#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/06/7150602.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7150602
loop_
_publ_author_name
'Rahanyan, Nelli'
'Linden, Anthony'
'Baldridge, Kim K.'
'Siegel, Jay S.'
_publ_section_title
;
 Diels--Alder reactions of 3,6-disubstituted 1,2,4,5-tetrazines.
 Synthesis and X-ray crystal structures of diazafluoranthene
 derivatives
;
_journal_issue                   10
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              2082
_journal_page_last               2092
_journal_paper_doi               10.1039/b820551e
_journal_volume                  7
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H16 N2 O2, 0.25(C H2 Cl2)'
_chemical_formula_sum            'C26.25 H16.5 Cl0.5 N2 O2'
_chemical_formula_weight         409.66
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      7
_symmetry_space_group_name_Hall  'P -2yac'
_symmetry_space_group_name_H-M   'P 1 n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             07-03-01
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.0449(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.4781(1)
_cell_length_b                   22.6399(3)
_cell_length_c                   23.8830(3)
_cell_measurement_reflns_used    109460
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.0
_cell_volume                     4012.95(9)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction
'DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL97 and PLATON (Spek, 2006)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 '65 mm CCD camera on \k goniostat'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scans with κ offsets'
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_source         'Nonius FR590 sealed tube generator'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0664
_diffrn_reflns_av_sigmaI/netI    0.0551
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            86266
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.49
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.150
_exptl_absorpt_correction_T_max  0.959
_exptl_absorpt_correction_T_min  0.850
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_crystal_colour            paleyellow
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1700
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.100
_refine_ls_abs_structure_details 'Flack & Bernardinelli (2000), ? Friedel pairs'
_refine_ls_abs_structure_Flack   0.11(5)
_refine_ls_extinction_coef       0.0092(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1132
_refine_ls_number_reflns         17993
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0563
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0815P)²+0.1428P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1289
_refine_ls_wR_factor_ref         0.1380
_reflns_number_gt                14245
_reflns_number_total             17993
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            b820551e.txt
_cod_data_source_block           SG0709
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'geom & difmap' was changed to
'mixed'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_original_formula_sum        'C26.25 H16.50 Cl0.50 N2 O2'
_cod_database_code               7150602
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.0082(3) 0.33989(8) 0.82821(8) 0.0307(4) Uani 1 1 d . . .
H1 H -0.070(6) 0.373(2) 0.8352(19) 0.078(13) Uiso 1 1 d . . .
O2 O 0.2387(3) 0.22916(9) 1.05204(9) 0.0456(6) Uani 1 1 d . . .
H2 H 0.2659 0.2498 1.0251 0.055 Uiso 1 1 calc R . .
N1 N 0.3589(3) 0.24676(9) 0.95402(10) 0.0305(5) Uani 1 1 d . . .
N2 N 0.3536(3) 0.28804(10) 0.91357(10) 0.0305(5) Uani 1 1 d . . .
C3 C 0.3209(3) 0.27335(12) 0.85966(12) 0.0265(6) Uani 1 1 d . . .
C4 C 0.2898(3) 0.21394(11) 0.84396(11) 0.0256(5) Uani 1 1 d . . .
C5 C 0.2492(3) 0.18717(12) 0.78818(12) 0.0274(6) Uani 1 1 d . . .
C6 C 0.2354(4) 0.20629(13) 0.73359(12) 0.0309(6) Uani 1 1 d . . .
H61 H 0.2547 0.2467 0.7255 0.037 Uiso 1 1 calc R . .
C7 C 0.1920(4) 0.16531(13) 0.68913(13) 0.0373(7) Uani 1 1 d . . .
H71 H 0.1891 0.1783 0.6512 0.045 Uiso 1 1 calc R . .
C8 C 0.1539(4) 0.10695(13) 0.69960(12) 0.0351(7) Uani 1 1 d . . .
H81 H 0.1236 0.0805 0.6690 0.042 Uiso 1 1 calc R . .
C9 C 0.1598(3) 0.08630(12) 0.75593(11) 0.0274(6) Uani 1 1 d . . .
C10 C 0.1139(3) 0.02901(12) 0.77385(13) 0.0318(6) Uani 1 1 d . . .
H10 H 0.0799 -0.0008 0.7467 0.038 Uiso 1 1 calc R . .
C11 C 0.1185(3) 0.01654(11) 0.83082(12) 0.0299(6) Uani 1 1 d . . .
H11 H 0.0819 -0.0215 0.8418 0.036 Uiso 1 1 calc R . .
C12 C 0.1759(3) 0.05855(12) 0.87312(12) 0.0271(6) Uani 1 1 d . . .
H12 H 0.1791 0.0487 0.9119 0.033 Uiso 1 1 calc R . .
C13 C 0.2273(3) 0.11424(11) 0.85727(12) 0.0253(5) Uani 1 1 d . . .
C14 C 0.2847(3) 0.17049(11) 0.88613(11) 0.0255(5) Uani 1 1 d . . .
C15 C 0.3270(3) 0.18889(11) 0.94250(11) 0.0257(5) Uani 1 1 d . . .
C16 C 0.2118(3) 0.12673(11) 0.79842(11) 0.0253(5) Uani 1 1 d . . .
C17 C 0.3144(3) 0.32219(11) 0.81795(12) 0.0275(6) Uani 1 1 d . . .
C18 C 0.1573(3) 0.35494(11) 0.80359(11) 0.0251(5) Uani 1 1 d . . .
C19 C 0.1531(4) 0.40000(11) 0.76410(11) 0.0272(6) Uani 1 1 d . . .
H19 H 0.0465 0.4226 0.7548 0.033 Uiso 1 1 calc R . .
C20 C 0.3046(4) 0.41182(12) 0.73840(12) 0.0328(6) Uani 1 1 d . . .
H20 H 0.3010 0.4423 0.7109 0.039 Uiso 1 1 calc R . .
C21 C 0.4614(4) 0.37996(13) 0.75207(13) 0.0365(7) Uani 1 1 d . . .
H21 H 0.5650 0.3887 0.7342 0.044 Uiso 1 1 calc R . .
C22 C 0.4675(4) 0.33567(12) 0.79156(13) 0.0337(6) Uani 1 1 d . . .
H22 H 0.5757 0.3140 0.8011 0.040 Uiso 1 1 calc R . .
C23 C 0.3352(4) 0.15103(12) 0.99298(12) 0.0297(6) Uani 1 1 d . . .
C24 C 0.2858(4) 0.17247(13) 1.04441(12) 0.0336(6) Uani 1 1 d . . .
C25 C 0.2778(5) 0.13350(14) 1.08964(13) 0.0443(8) Uani 1 1 d . . .
H25 H 0.2351 0.1472 1.1232 0.053 Uiso 1 1 calc R . .
C26 C 0.3310(5) 0.07582(14) 1.08588(14) 0.0480(9) Uani 1 1 d . . .
H26 H 0.3255 0.0498 1.1169 0.058 Uiso 1 1 calc R . .
C27 C 0.3929(4) 0.05521(13) 1.03693(13) 0.0417(8) Uani 1 1 d . . .
H27 H 0.4344 0.0157 1.0350 0.050 Uiso 1 1 calc R . .
C28 C 0.3939(4) 0.09211(12) 0.99144(13) 0.0329(6) Uani 1 1 d . . .
H28 H 0.4352 0.0775 0.9580 0.039 Uiso 1 1 calc R . .
O3 O 0.8948(3) -0.08936(9) 0.92929(9) 0.0329(4) Uani 1 1 d . . .
H3 H 0.975(6) -0.122(2) 0.9365(18) 0.076(13) Uiso 1 1 d . . .
O4 O 0.3006(3) -0.03830(10) 0.66998(9) 0.0396(5) Uani 1 1 d . . .
H4 H 0.358(7) -0.053(3) 0.698(2) 0.099(18) Uiso 1 1 d . . .
N31 N 0.5115(3) -0.04943(10) 0.76632(9) 0.0288(5) Uani 1 1 d . . .
N32 N 0.5134(3) -0.07229(10) 0.81754(9) 0.0270(5) Uani 1 1 d . . .
C33 C 0.5908(3) -0.04310(11) 0.86298(11) 0.0234(5) Uani 1 1 d . . .
C34 C 0.6605(3) 0.01308(11) 0.85732(10) 0.0229(5) Uani 1 1 d . . .
C35 C 0.7393(3) 0.05504(11) 0.90003(11) 0.0226(5) Uani 1 1 d . . .
C36 C 0.7982(4) 0.05201(12) 0.95678(11) 0.0295(6) Uani 1 1 d . . .
H36 H 0.7925 0.0161 0.9770 0.035 Uiso 1 1 calc R . .
C37 C 0.8682(4) 0.10434(13) 0.98438(12) 0.0329(6) Uani 1 1 d . . .
H37 H 0.9102 0.1027 1.0235 0.040 Uiso 1 1 calc R . .
C38 C 0.8771(4) 0.15689(12) 0.95653(12) 0.0322(6) Uani 1 1 d . . .
H38 H 0.9208 0.1912 0.9766 0.039 Uiso 1 1 calc R . .
C39 C 0.8210(3) 0.16010(12) 0.89746(12) 0.0279(6) Uani 1 1 d . . .
C40 C 0.8317(4) 0.21019(12) 0.86235(13) 0.0308(6) Uani 1 1 d . . .
H40 H 0.8759 0.2467 0.8780 0.037 Uiso 1 1 calc R . .
C41 C 0.7777(4) 0.20530(12) 0.80564(13) 0.0319(6) Uani 1 1 d . . .
H41 H 0.7861 0.2392 0.7826 0.038 Uiso 1 1 calc R . .
C42 C 0.7105(3) 0.15287(12) 0.77976(12) 0.0283(6) Uani 1 1 d . . .
H42 H 0.6713 0.1518 0.7404 0.034 Uiso 1 1 calc R . .
C43 C 0.7023(3) 0.10291(11) 0.81244(11) 0.0242(5) Uani 1 1 d . . .
C44 C 0.6446(3) 0.04059(11) 0.80418(10) 0.0229(5) Uani 1 1 d . . .
C45 C 0.5750(3) 0.00525(11) 0.75765(11) 0.0240(5) Uani 1 1 d . . .
C46 C 0.7556(3) 0.10893(11) 0.87124(11) 0.0245(5) Uani 1 1 d . . .
C47 C 0.5790(3) -0.07388(11) 0.91780(11) 0.0244(5) Uani 1 1 d . . .
C48 C 0.7323(3) -0.09699(11) 0.94863(11) 0.0246(5) Uani 1 1 d . . .
C49 C 0.7166(4) -0.12787(13) 0.99822(12) 0.0333(6) Uani 1 1 d . . .
H49 H 0.8207 -0.1448 1.0189 0.040 Uiso 1 1 calc R . .
C50 C 0.5504(4) -0.13408(13) 1.01760(12) 0.0331(6) Uani 1 1 d . . .
H50 H 0.5408 -0.1552 1.0515 0.040 Uiso 1 1 calc R . .
C51 C 0.3994(4) -0.10958(12) 0.98772(12) 0.0325(6) Uani 1 1 d . . .
H51 H 0.2855 -0.1133 1.0012 0.039 Uiso 1 1 calc R . .
C52 C 0.4141(4) -0.07952(12) 0.93794(11) 0.0286(6) Uani 1 1 d . . .
H52 H 0.3098 -0.0626 0.9174 0.034 Uiso 1 1 calc R . .
C53 C 0.5637(3) 0.02201(11) 0.69716(11) 0.0264(5) Uani 1 1 d . . .
C54 C 0.4280(4) -0.00041(13) 0.65682(12) 0.0298(6) Uani 1 1 d . . .
C55 C 0.4186(4) 0.01658(14) 0.60120(12) 0.0377(7) Uani 1 1 d . . .
H55 H 0.3220 0.0031 0.5747 0.045 Uiso 1 1 calc R . .
C56 C 0.5511(4) 0.05374(16) 0.58344(13) 0.0437(8) Uani 1 1 d . . .
H56 H 0.5453 0.0648 0.5449 0.052 Uiso 1 1 calc R . .
C57 C 0.6912(4) 0.07434(14) 0.62252(12) 0.0375(7) Uani 1 1 d . . .
H57 H 0.7828 0.0989 0.6109 0.045 Uiso 1 1 calc R . .
C58 C 0.6942(4) 0.05847(13) 0.67840(12) 0.0310(6) Uani 1 1 d . . .
H58 H 0.7887 0.0729 0.7051 0.037 Uiso 1 1 calc R . .
O5 O 0.5651(3) 0.39073(9) 0.92264(9) 0.0341(5) Uani 1 1 d . . .
H5 H 0.476(6) 0.3590(19) 0.9179(17) 0.068(12) Uiso 1 1 d . . .
O6 O 0.5710(3) 0.51184(9) 0.70427(9) 0.0395(5) Uani 1 1 d . . .
H6 H 0.6142 0.4894 0.7305 0.047 Uiso 1 1 calc R . .
N61 N 0.7896(3) 0.48726(10) 0.79950(9) 0.0278(5) Uani 1 1 d . . .
N62 N 0.8210(3) 0.44564(10) 0.83964(9) 0.0278(5) Uani 1 1 d . . .
C63 C 0.8439(3) 0.46156(12) 0.89434(11) 0.0256(5) Uani 1 1 d . . .
C64 C 0.8335(3) 0.52027(11) 0.91001(11) 0.0243(5) Uani 1 1 d . . .
C65 C 0.8424(3) 0.54809(11) 0.96616(11) 0.0266(5) Uani 1 1 d . . .
C66 C 0.8845(4) 0.52879(12) 1.02151(12) 0.0305(6) Uani 1 1 d . . .
H66 H 0.9169 0.4889 1.0297 0.037 Uiso 1 1 calc R . .
C67 C 0.8775(4) 0.57020(14) 1.06497(12) 0.0362(7) Uani 1 1 d . . .
H67 H 0.9083 0.5578 1.1029 0.043 Uiso 1 1 calc R . .
C68 C 0.8279(4) 0.62781(13) 1.05469(12) 0.0342(6) Uani 1 1 d . . .
H68 H 0.8242 0.6542 1.0855 0.041 Uiso 1 1 calc R . .
C69 C 0.7824(3) 0.64860(12) 0.99897(12) 0.0283(6) Uani 1 1 d . . .
C70 C 0.7172(4) 0.70522(13) 0.98060(12) 0.0314(6) Uani 1 1 d . . .
H70 H 0.7040 0.7350 1.0078 0.038 Uiso 1 1 calc R . .
C71 C 0.6732(4) 0.71773(12) 0.92457(12) 0.0304(6) Uani 1 1 d . . .
H711 H 0.6270 0.7557 0.9139 0.036 Uiso 1 1 calc R . .
C72 C 0.6947(3) 0.67551(12) 0.88195(12) 0.0278(6) Uani 1 1 d . . .
H72 H 0.6641 0.6852 0.8433 0.033 Uiso 1 1 calc R . .
C73 C 0.7608(3) 0.62011(11) 0.89738(11) 0.0255(5) Uani 1 1 d . . .
C74 C 0.7894(3) 0.56373(11) 0.86835(11) 0.0240(5) Uani 1 1 d . . .
C75 C 0.7757(3) 0.54498(11) 0.81224(11) 0.0254(5) Uani 1 1 d . . .
C76 C 0.7988(3) 0.60784(11) 0.95621(11) 0.0256(5) Uani 1 1 d . . .
C77 C 0.8761(4) 0.41276(11) 0.93631(11) 0.0280(6) Uani 1 1 d . . .
C78 C 0.7312(3) 0.37727(11) 0.94862(11) 0.0261(5) Uani 1 1 d . . .
C79 C 0.7623(4) 0.33222(12) 0.98811(12) 0.0321(6) Uani 1 1 d . . .
H79 H 0.6652 0.3079 0.9963 0.039 Uiso 1 1 calc R . .
C80 C 0.9337(4) 0.32250(13) 1.01572(12) 0.0351(7) Uani 1 1 d . . .
H80 H 0.9540 0.2917 1.0428 0.042 Uiso 1 1 calc R . .
C81 C 1.0745(4) 0.35760(13) 1.00383(13) 0.0347(6) Uani 1 1 d . . .
H811 H 1.1912 0.3515 1.0236 0.042 Uiso 1 1 calc R . .
C82 C 1.0483(4) 0.40107(13) 0.96395(12) 0.0332(6) Uani 1 1 d . . .
H82 H 1.1481 0.4236 0.9549 0.040 Uiso 1 1 calc R . .
C83 C 0.7477(3) 0.58424(12) 0.76179(11) 0.0264(6) Uani 1 1 d . . .
C84 C 0.6497(4) 0.56594(12) 0.71108(12) 0.0306(6) Uani 1 1 d . . .
C85 C 0.6236(4) 0.60434(14) 0.66504(13) 0.0395(7) Uani 1 1 d . . .
H85 H 0.5540 0.5920 0.6311 0.047 Uiso 1 1 calc R . .
C86 C 0.6983(4) 0.66012(13) 0.66865(13) 0.0400(7) Uani 1 1 d . . .
H86 H 0.6785 0.6862 0.6373 0.048 Uiso 1 1 calc R . .
C87 C 0.8017(4) 0.67832(13) 0.71737(13) 0.0371(7) Uani 1 1 d . . .
H87 H 0.8562 0.7163 0.7194 0.044 Uiso 1 1 calc R . .
C88 C 0.8251(4) 0.64051(12) 0.76350(12) 0.0305(6) Uani 1 1 d . . .
H88 H 0.8956 0.6532 0.7971 0.037 Uiso 1 1 calc R . .
O7 O 0.3763(3) 0.81639(10) 0.83491(9) 0.0388(5) Uani 1 1 d . . .
H7 H 0.441(5) 0.8456(16) 0.8327(14) 0.040(9) Uiso 1 1 d . . .
O8 O -0.0236(3) 0.77192(9) 1.09465(8) 0.0349(5) Uani 1 1 d . . .
H8 H -0.0242 0.7871 1.0625 0.042 Uiso 1 1 calc R . .
N91 N 0.0993(3) 0.78372(9) 0.99517(9) 0.0252(5) Uani 1 1 d . . .
N92 N 0.0615(3) 0.80468(10) 0.94255(9) 0.0259(5) Uani 1 1 d . . .
C93 C 0.1120(3) 0.77507(11) 0.89873(10) 0.0248(5) Uani 1 1 d . . .
C94 C 0.1919(3) 0.71965(11) 0.90627(11) 0.0236(5) Uani 1 1 d . . .
C95 C 0.2382(3) 0.67504(12) 0.86574(11) 0.0281(6) Uani 1 1 d . . .
C96 C 0.2503(4) 0.67386(13) 0.80897(12) 0.0337(6) Uani 1 1 d . . .
H96 H 0.2278 0.7084 0.7866 0.040 Uiso 1 1 calc R . .
C97 C 0.2970(4) 0.62025(15) 0.78453(14) 0.0406(8) Uani 1 1 d . . .
H97 H 0.3054 0.6191 0.7452 0.049 Uiso 1 1 calc R . .
C98 C 0.3308(4) 0.56956(14) 0.81556(14) 0.0408(8) Uani 1 1 d . . .
H98 H 0.3561 0.5339 0.7972 0.049 Uiso 1 1 calc R . .
C99 C 0.3283(3) 0.56999(13) 0.87444(14) 0.0350(7) Uani 1 1 d . . .
C100 C 0.3677(4) 0.52308(13) 0.91292(16) 0.0410(8) Uani 1 1 d . . .
H100 H 0.3989 0.4854 0.8995 0.049 Uiso 1 1 calc R . .
C101 C 0.3614(4) 0.53156(13) 0.96957(15) 0.0403(7) Uani 1 1 d . . .
H101 H 0.3890 0.4992 0.9945 0.048 Uiso 1 1 calc R . .
C102 C 0.3151(4) 0.58673(12) 0.99250(14) 0.0333(6) Uani 1 1 d . . .
H102 H 0.3105 0.5911 1.0319 0.040 Uiso 1 1 calc R . .
C103 C 0.2773(3) 0.63328(11) 0.95661(12) 0.0270(6) Uani 1 1 d . . .
C104 C 0.2205(3) 0.69545(11) 0.96098(11) 0.0241(5) Uani 1 1 d . . .
C105 C 0.1837(3) 0.73198(11) 1.00603(11) 0.0224(5) Uani 1 1 d . . .
C106 C 0.2831(3) 0.62402(12) 0.89799(12) 0.0281(6) Uani 1 1 d . . .
C107 C 0.0659(4) 0.80432(12) 0.84278(11) 0.0289(6) Uani 1 1 d . . .
C108 C 0.2011(4) 0.82405(12) 0.81300(12) 0.0336(6) Uani 1 1 d . . .
C109 C 0.1565(5) 0.85305(15) 0.76145(13) 0.0482(9) Uani 1 1 d . . .
H109 H 0.2491 0.8666 0.7407 0.058 Uiso 1 1 calc R . .
C110 C -0.0211(5) 0.86185(15) 0.74082(14) 0.0506(9) Uani 1 1 d . . .
H110 H -0.0497 0.8815 0.7057 0.061 Uiso 1 1 calc R . .
C111 C -0.1602(5) 0.84272(15) 0.77008(13) 0.0428(7) Uani 1 1 d . . .
H111 H -0.2827 0.8494 0.7557 0.051 Uiso 1 1 calc R . .
C112 C -0.1138(4) 0.81324(13) 0.82161(12) 0.0348(6) Uani 1 1 d . . .
H112 H -0.2062 0.7993 0.8422 0.042 Uiso 1 1 calc R . .
C113 C 0.2342(3) 0.71893(11) 1.06663(11) 0.0264(6) Uani 1 1 d . . .
C114 C 0.1271(3) 0.73903(12) 1.10689(11) 0.0275(6) Uani 1 1 d . . .
C115 C 0.1758(4) 0.72508(13) 1.16444(11) 0.0327(6) Uani 1 1 d . . .
H115 H 0.1025 0.7378 1.1919 0.039 Uiso 1 1 calc R . .
C116 C 0.3294(4) 0.69307(14) 1.18035(12) 0.0369(7) Uani 1 1 d . . .
H116 H 0.3598 0.6827 1.2189 0.044 Uiso 1 1 calc R . .
C117 C 0.4400(4) 0.67583(13) 1.14133(12) 0.0337(6) Uani 1 1 d . . .
H117 H 0.5487 0.6552 1.1532 0.040 Uiso 1 1 calc R . .
C118 C 0.3932(4) 0.68847(12) 1.08552(12) 0.0297(6) Uani 1 1 d . . .
H118 H 0.4703 0.6763 1.0589 0.036 Uiso 1 1 calc R . .
Cl1 Cl 0.45277(14) 0.51591(4) 1.13547(4) 0.0574(2) Uani 1 1 d . . .
Cl2 Cl 0.60107(18) 0.41219(5) 1.08669(5) 0.0779(3) Uani 1 1 d . . .
C119 C 0.5723(5) 0.44850(16) 1.14895(16) 0.0568(9) Uani 1 1 d . . .
H119 H 0.6917 0.4568 1.1703 0.068 Uiso 1 1 calc R . .
H120 H 0.5051 0.4227 1.1725 0.068 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_number_in_cell
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 210 0.0033 0.0016
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
H H 132 0.0000 0.0000
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
Cl Cl 4 0.1484 0.1585
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
N N 16 0.0061 0.0033
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
O O 16 0.0106 0.0060
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18 O1 H1 115(3) . . ?
C24 O2 H2 109.5 . . ?
N2 N1 C15 122.6(2) . . ?
C3 N2 N1 120.8(2) . . ?
N2 C3 C4 120.3(2) . . ?
N2 C3 C17 116.9(2) . . ?
C4 C3 C17 122.8(2) . . ?
C3 C4 C14 119.6(2) . . ?
C3 C4 C5 130.4(2) . . ?
C14 C4 C5 109.9(2) . . ?
C6 C5 C16 118.4(3) . . ?
C6 C5 C4 136.2(3) . . ?
C16 C5 C4 105.4(2) . . ?
C5 C6 C7 119.4(3) . . ?
C5 C6 H61 120.3 . . ?
C7 C6 H61 120.3 . . ?
C8 C7 C6 121.6(3) . . ?
C8 C7 H71 119.2 . . ?
C6 C7 H71 119.2 . . ?
C7 C8 C9 120.2(3) . . ?
C7 C8 H81 119.9 . . ?
C9 C8 H81 119.9 . . ?
C16 C9 C8 116.7(2) . . ?
C16 C9 C10 116.0(2) . . ?
C8 C9 C10 127.2(3) . . ?
C11 C10 C9 120.3(3) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 122.2(2) . . ?
C10 C11 H11 118.9 . . ?
C12 C11 H11 118.9 . . ?
C13 C12 C11 119.1(3) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C12 C13 C16 117.3(2) . . ?
C12 C13 C14 136.7(3) . . ?
C16 C13 C14 105.7(2) . . ?
C15 C14 C4 117.0(2) . . ?
C15 C14 C13 135.7(2) . . ?
C4 C14 C13 107.3(2) . . ?
N1 C15 C14 119.6(2) . . ?
N1 C15 C23 114.1(2) . . ?
C14 C15 C23 126.3(2) . . ?
C9 C16 C5 123.5(2) . . ?
C9 C16 C13 124.9(2) . . ?
C5 C16 C13 111.5(2) . . ?
C18 C17 C22 118.8(2) . . ?
C18 C17 C3 121.2(2) . . ?
C22 C17 C3 120.0(2) . . ?
O1 C18 C19 121.6(2) . . ?
O1 C18 C17 117.9(2) . . ?
C19 C18 C17 120.4(2) . . ?
C20 C19 C18 119.6(3) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C19 C20 C21 120.9(3) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C22 C21 C20 119.9(3) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C17 120.4(3) . . ?
C21 C22 H22 119.8 . . ?
C17 C22 H22 119.8 . . ?
C28 C23 C24 117.7(3) . . ?
C28 C23 C15 120.8(3) . . ?
C24 C23 C15 121.5(2) . . ?
O2 C24 C25 117.3(3) . . ?
O2 C24 C23 123.0(3) . . ?
C25 C24 C23 119.7(3) . . ?
C26 C25 C24 120.6(3) . . ?
C26 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
C25 C26 C27 120.3(3) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C28 C27 C26 119.8(3) . . ?
C28 C27 H27 120.1 . . ?
C26 C27 H27 120.1 . . ?
C27 C28 C23 121.7(3) . . ?
C27 C28 H28 119.2 . . ?
C23 C28 H28 119.2 . . ?
C48 O3 H3 114(3) . . ?
C54 O4 H4 98(4) . . ?
N32 N31 C45 122.3(2) . . ?
N31 N32 C33 120.6(2) . . ?
N32 C33 C34 120.2(2) . . ?
N32 C33 C47 114.4(2) . . ?
C34 C33 C47 125.1(2) . . ?
C33 C34 C44 120.2(2) . . ?
C33 C34 C35 130.6(2) . . ?
C44 C34 C35 108.9(2) . . ?
C36 C35 C46 119.1(2) . . ?
C36 C35 C34 135.1(2) . . ?
C46 C35 C34 105.8(2) . . ?
C35 C36 C37 118.1(3) . . ?
C35 C36 H36 121.0 . . ?
C37 C36 H36 121.0 . . ?
C38 C37 C36 122.4(3) . . ?
C38 C37 H37 118.8 . . ?
C36 C37 H37 118.8 . . ?
C37 C38 C39 120.0(3) . . ?
C37 C38 H38 120.0 . . ?
C39 C38 H38 120.0 . . ?
C46 C39 C40 116.5(2) . . ?
C46 C39 C38 116.9(2) . . ?
C40 C39 C38 126.5(3) . . ?
C41 C40 C39 119.3(3) . . ?
C41 C40 H40 120.4 . . ?
C39 C40 H40 120.4 . . ?
C40 C41 C42 123.4(2) . . ?
C40 C41 H41 118.3 . . ?
C42 C41 H41 118.3 . . ?
C43 C42 C41 118.9(3) . . ?
C43 C42 H42 120.6 . . ?
C41 C42 H42 120.6 . . ?
C42 C43 C46 117.1(2) . . ?
C42 C43 C44 137.5(2) . . ?
C46 C43 C44 105.4(2) . . ?
C34 C44 C45 116.1(2) . . ?
C34 C44 C43 108.1(2) . . ?
C45 C44 C43 135.7(2) . . ?
N31 C45 C44 120.0(2) . . ?
N31 C45 C53 113.8(2) . . ?
C44 C45 C53 126.2(2) . . ?
C39 C46 C35 123.5(2) . . ?
C39 C46 C43 124.9(2) . . ?
C35 C46 C43 111.6(2) . . ?
C52 C47 C48 119.6(2) . . ?
C52 C47 C33 119.9(2) . . ?
C48 C47 C33 120.5(2) . . ?
O3 C48 C47 119.0(2) . . ?
O3 C48 C49 121.6(2) . . ?
C47 C48 C49 119.4(2) . . ?
C50 C49 C48 120.5(3) . . ?
C50 C49 H49 119.8 . . ?
C48 C49 H49 119.8 . . ?
C51 C50 C49 119.9(3) . . ?
C51 C50 H50 120.0 . . ?
C49 C50 H50 120.0 . . ?
C50 C51 C52 119.7(3) . . ?
C50 C51 H51 120.1 . . ?
C52 C51 H51 120.1 . . ?
C47 C52 C51 120.8(3) . . ?
C47 C52 H52 119.6 . . ?
C51 C52 H52 119.6 . . ?
C58 C53 C54 117.9(2) . . ?
C58 C53 C45 120.4(2) . . ?
C54 C53 C45 121.6(2) . . ?
O4 C54 C55 116.7(2) . . ?
O4 C54 C53 122.8(2) . . ?
C55 C54 C53 120.5(3) . . ?
C54 C55 C56 120.3(3) . . ?
C54 C55 H55 119.9 . . ?
C56 C55 H55 119.9 . . ?
C57 C56 C55 119.9(3) . . ?
C57 C56 H56 120.1 . . ?
C55 C56 H56 120.1 . . ?
C58 C57 C56 118.8(3) . . ?
C58 C57 H57 120.6 . . ?
C56 C57 H57 120.6 . . ?
C57 C58 C53 122.4(3) . . ?
C57 C58 H58 118.8 . . ?
C53 C58 H58 118.8 . . ?
C78 O5 H5 117(2) . . ?
C84 O6 H6 109.5 . . ?
N62 N61 C75 122.0(2) . . ?
N61 N62 C63 119.7(2) . . ?
N62 C63 C64 121.0(2) . . ?
N62 C63 C77 116.4(2) . . ?
C64 C63 C77 122.6(2) . . ?
C63 C64 C74 119.7(2) . . ?
C63 C64 C65 131.1(2) . . ?
C74 C64 C65 108.9(2) . . ?
C66 C65 C76 118.9(2) . . ?
C66 C65 C64 135.2(2) . . ?
C76 C65 C64 105.9(2) . . ?
C65 C66 C67 117.9(3) . . ?
C65 C66 H66 121.1 . . ?
C67 C66 H66 121.1 . . ?
C68 C67 C66 122.5(3) . . ?
C68 C67 H67 118.8 . . ?
C66 C67 H67 118.8 . . ?
C67 C68 C69 121.0(3) . . ?
C67 C68 H68 119.5 . . ?
C69 C68 H68 119.5 . . ?
C76 C69 C68 115.9(2) . . ?
C76 C69 C70 115.4(2) . . ?
C68 C69 C70 128.7(3) . . ?
C71 C70 C69 121.4(3) . . ?
C71 C70 H70 119.3 . . ?
C69 C70 H70 119.3 . . ?
C70 C71 C72 121.8(3) . . ?
C70 C71 H711 119.1 . . ?
C72 C71 H711 119.1 . . ?
C73 C72 C71 119.2(3) . . ?
C73 C72 H72 120.4 . . ?
C71 C72 H72 120.4 . . ?
C72 C73 C76 117.5(2) . . ?
C72 C73 C74 136.5(3) . . ?
C76 C73 C74 105.7(2) . . ?
C75 C74 C64 116.6(2) . . ?
C75 C74 C73 135.5(2) . . ?
C64 C74 C73 107.8(2) . . ?
N61 C75 C74 120.8(2) . . ?
N61 C75 C83 113.7(2) . . ?
C74 C75 C83 125.5(2) . . ?
C69 C76 C65 123.6(2) . . ?
C69 C76 C73 124.6(2) . . ?
C65 C76 C73 111.6(2) . . ?
C82 C77 C78 118.8(2) . . ?
C82 C77 C63 121.4(2) . . ?
C78 C77 C63 119.8(2) . . ?
O5 C78 C79 123.0(2) . . ?
O5 C78 C77 117.5(2) . . ?
C79 C78 C77 119.4(2) . . ?
C80 C79 C78 120.5(3) . . ?
C80 C79 H79 119.7 . . ?
C78 C79 H79 119.7 . . ?
C81 C80 C79 119.8(3) . . ?
C81 C80 H80 120.1 . . ?
C79 C80 H80 120.1 . . ?
C82 C81 C80 120.8(3) . . ?
C82 C81 H811 119.6 . . ?
C80 C81 H811 119.6 . . ?
C81 C82 C77 120.7(3) . . ?
C81 C82 H82 119.7 . . ?
C77 C82 H82 119.7 . . ?
C88 C83 C84 117.8(2) . . ?
C88 C83 C75 120.2(2) . . ?
C84 C83 C75 122.0(2) . . ?
O6 C84 C85 116.7(2) . . ?
O6 C84 C83 122.9(2) . . ?
C85 C84 C83 120.3(3) . . ?
C86 C85 C84 120.3(3) . . ?
C86 C85 H85 119.9 . . ?
C84 C85 H85 119.9 . . ?
C87 C86 C85 120.5(3) . . ?
C87 C86 H86 119.8 . . ?
C85 C86 H86 119.8 . . ?
C86 C87 C88 119.2(3) . . ?
C86 C87 H87 120.4 . . ?
C88 C87 H87 120.4 . . ?
C87 C88 C83 121.8(3) . . ?
C87 C88 H88 119.1 . . ?
C83 C88 H88 119.1 . . ?
C108 O7 H7 115(2) . . ?
C114 O8 H8 109.5 . . ?
N92 N91 C105 122.0(2) . . ?
C93 N92 N91 120.6(2) . . ?
N92 C93 C94 120.6(2) . . ?
N92 C93 C107 115.0(2) . . ?
C94 C93 C107 124.3(2) . . ?
C93 C94 C104 119.0(2) . . ?
C93 C94 C95 131.8(2) . . ?
C104 C94 C95 108.8(2) . . ?
C96 C95 C106 119.0(3) . . ?
C96 C95 C94 135.6(3) . . ?
C106 C95 C94 105.3(2) . . ?
C95 C96 C97 118.5(3) . . ?
C95 C96 H96 120.8 . . ?
C97 C96 H96 120.8 . . ?
C98 C97 C96 122.3(3) . . ?
C98 C97 H97 118.8 . . ?
C96 C97 H97 118.8 . . ?
C97 C98 C99 120.6(3) . . ?
C97 C98 H98 119.7 . . ?
C99 C98 H98 119.7 . . ?
C106 C99 C98 116.0(3) . . ?
C106 C99 C100 115.8(3) . . ?
C98 C99 C100 128.1(3) . . ?
C101 C100 C99 120.4(3) . . ?
C101 C100 H100 119.8 . . ?
C99 C100 H100 119.8 . . ?
C100 C101 C102 122.8(3) . . ?
C100 C101 H101 118.6 . . ?
C102 C101 H101 118.6 . . ?
C103 C102 C101 118.5(3) . . ?
C103 C102 H102 120.8 . . ?
C101 C102 H102 120.8 . . ?
C102 C103 C106 118.4(3) . . ?
C102 C103 C104 136.9(3) . . ?
C106 C103 C104 104.7(2) . . ?
C94 C104 C105 117.2(2) . . ?
C94 C104 C103 108.5(2) . . ?
C105 C104 C103 134.2(2) . . ?
N91 C105 C104 119.7(2) . . ?
N91 C105 C113 114.9(2) . . ?
C104 C105 C113 125.3(2) . . ?
C99 C106 C95 123.3(3) . . ?
C99 C106 C103 124.1(3) . . ?
C95 C106 C103 112.6(2) . . ?
C108 C107 C112 120.1(3) . . ?
C108 C107 C93 120.1(2) . . ?
C112 C107 C93 119.7(2) . . ?
O7 C108 C107 119.5(2) . . ?
O7 C108 C109 120.8(3) . . ?
C107 C108 C109 119.7(3) . . ?
C110 C109 C108 119.9(3) . . ?
C110 C109 H109 120.0 . . ?
C108 C109 H109 120.0 . . ?
C109 C110 C111 121.6(3) . . ?
C109 C110 H110 119.2 . . ?
C111 C110 H110 119.2 . . ?
C110 C111 C112 117.9(3) . . ?
C110 C111 H111 121.0 . . ?
C112 C111 H111 121.0 . . ?
C107 C112 C111 120.7(3) . . ?
C107 C112 H112 119.6 . . ?
C111 C112 H112 119.6 . . ?
C118 C113 C114 118.3(2) . . ?
C118 C113 C105 121.2(2) . . ?
C114 C113 C105 120.5(2) . . ?
O8 C114 C113 124.2(2) . . ?
O8 C114 C115 116.2(2) . . ?
C113 C114 C115 119.6(2) . . ?
C116 C115 C114 119.6(3) . . ?
C116 C115 H115 120.2 . . ?
C114 C115 H115 120.2 . . ?
C115 C116 C117 121.0(3) . . ?
C115 C116 H116 119.5 . . ?
C117 C116 H116 119.5 . . ?
C118 C117 C116 119.8(3) . . ?
C118 C117 H117 120.1 . . ?
C116 C117 H117 120.1 . . ?
C117 C118 C113 121.6(3) . . ?
C117 C118 H118 119.2 . . ?
C113 C118 H118 119.2 . . ?
Cl2 C119 Cl1 111.3(2) . . ?
Cl2 C119 H119 109.4 . . ?
Cl1 C119 H119 109.4 . . ?
Cl2 C119 H120 109.4 . . ?
Cl1 C119 H120 109.4 . . ?
H119 C119 H120 108.0 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C18 1.366(3) . ?
O1 H1 0.97(5) . ?
O2 C24 1.349(3) . ?
O2 H2 0.8400 . ?
N1 N2 1.341(3) . ?
N1 C15 1.354(3) . ?
N2 C3 1.323(4) . ?
C3 C4 1.408(4) . ?
C3 C17 1.485(4) . ?
C4 C14 1.412(4) . ?
C4 C5 1.461(4) . ?
C5 C6 1.366(4) . ?
C5 C16 1.424(4) . ?
C6 C7 1.417(4) . ?
C6 H61 0.9500 . ?
C7 C8 1.381(4) . ?
C7 H71 0.9500 . ?
C8 C9 1.420(4) . ?
C8 H81 0.9500 . ?
C9 C16 1.386(4) . ?
C9 C10 1.421(4) . ?
C10 C11 1.386(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.415(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.384(4) . ?
C12 H12 0.9500 . ?
C13 C16 1.425(4) . ?
C13 C14 1.486(4) . ?
C14 C15 1.408(4) . ?
C15 C23 1.474(4) . ?
C17 C18 1.396(4) . ?
C17 C22 1.406(4) . ?
C18 C19 1.387(4) . ?
C19 C20 1.380(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.381(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.374(4) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C28 1.406(4) . ?
C23 C24 1.412(4) . ?
C24 C25 1.402(4) . ?
C25 C26 1.371(5) . ?
C25 H25 0.9500 . ?
C26 C27 1.390(5) . ?
C26 H26 0.9500 . ?
C27 C28 1.371(4) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
O3 C48 1.363(3) . ?
O3 H3 0.96(5) . ?
O4 C54 1.347(3) . ?
O4 H4 0.82(5) . ?
N31 N32 1.327(3) . ?
N31 C45 1.351(3) . ?
N32 C33 1.340(3) . ?
C33 C34 1.388(4) . ?
C33 C47 1.495(4) . ?
C34 C44 1.405(3) . ?
C34 C35 1.464(4) . ?
C35 C36 1.375(4) . ?
C35 C46 1.413(4) . ?
C36 C37 1.424(4) . ?
C36 H36 0.9500 . ?
C37 C38 1.369(4) . ?
C37 H37 0.9500 . ?
C38 C39 1.423(4) . ?
C38 H38 0.9500 . ?
C39 C46 1.378(4) . ?
C39 C40 1.419(4) . ?
C40 C41 1.370(4) . ?
C40 H40 0.9500 . ?
C41 C42 1.403(4) . ?
C41 H41 0.9500 . ?
C42 C43 1.380(4) . ?
C42 H42 0.9500 . ?
C43 C46 1.418(4) . ?
C43 C44 1.482(4) . ?
C44 C45 1.416(4) . ?
C45 C53 1.486(4) . ?
C47 C52 1.384(4) . ?
C47 C48 1.386(4) . ?
C48 C49 1.392(4) . ?
C49 C50 1.385(4) . ?
C49 H49 0.9500 . ?
C50 C51 1.377(4) . ?
C50 H50 0.9500 . ?
C51 C52 1.386(4) . ?
C51 H51 0.9500 . ?
C52 H52 0.9500 . ?
C53 C58 1.393(4) . ?
C53 C54 1.406(4) . ?
C54 C55 1.376(4) . ?
C55 C56 1.404(5) . ?
C55 H55 0.9500 . ?
C56 C57 1.395(4) . ?
C56 H56 0.9500 . ?
C57 C58 1.380(4) . ?
C57 H57 0.9500 . ?
C58 H58 0.9500 . ?
O5 C78 1.353(3) . ?
O5 H5 0.98(5) . ?
O6 C84 1.360(3) . ?
O6 H6 0.8400 . ?
N61 N62 1.344(3) . ?
N61 C75 1.348(4) . ?
N62 C63 1.346(3) . ?
C63 C64 1.386(4) . ?
C63 C77 1.491(4) . ?
C64 C74 1.409(4) . ?
C64 C65 1.476(4) . ?
C65 C66 1.391(4) . ?
C65 C76 1.405(4) . ?
C66 C67 1.404(4) . ?
C66 H66 0.9500 . ?
C67 C68 1.370(4) . ?
C67 H67 0.9500 . ?
C68 C69 1.413(4) . ?
C68 H68 0.9500 . ?
C69 C76 1.393(4) . ?
C69 C70 1.422(4) . ?
C70 C71 1.368(4) . ?
C70 H70 0.9500 . ?
C71 C72 1.420(4) . ?
C71 H711 0.9500 . ?
C72 C73 1.381(4) . ?
C72 H72 0.9500 . ?
C73 C76 1.426(4) . ?
C73 C74 1.481(4) . ?
C74 C75 1.397(4) . ?
C75 C83 1.491(4) . ?
C77 C82 1.398(4) . ?
C77 C78 1.409(4) . ?
C78 C79 1.389(4) . ?
C79 C80 1.385(4) . ?
C79 H79 0.9500 . ?
C80 C81 1.376(4) . ?
C80 H80 0.9500 . ?
C81 C82 1.367(4) . ?
C81 H811 0.9500 . ?
C82 H82 0.9500 . ?
C83 C88 1.398(4) . ?
C83 C84 1.399(4) . ?
C84 C85 1.397(4) . ?
C85 C86 1.380(4) . ?
C85 H85 0.9500 . ?
C86 C87 1.378(4) . ?
C86 H86 0.9500 . ?
C87 C88 1.389(4) . ?
C87 H87 0.9500 . ?
C88 H88 0.9500 . ?
O7 C108 1.361(4) . ?
O7 H7 0.82(4) . ?
O8 C114 1.352(3) . ?
O8 H8 0.8400 . ?
N91 N92 1.341(3) . ?
N91 C105 1.341(3) . ?
N92 C93 1.336(3) . ?
C93 C94 1.392(4) . ?
C93 C107 1.493(4) . ?
C94 C104 1.409(4) . ?
C94 C95 1.469(4) . ?
C95 C96 1.370(4) . ?
C95 C106 1.406(4) . ?
C96 C97 1.409(4) . ?
C96 H96 0.9500 . ?
C97 C98 1.373(5) . ?
C97 H97 0.9500 . ?
C98 C99 1.408(5) . ?
C98 H98 0.9500 . ?
C99 C106 1.405(4) . ?
C99 C100 1.412(5) . ?
C100 C101 1.373(5) . ?
C100 H100 0.9500 . ?
C101 C102 1.424(4) . ?
C101 H101 0.9500 . ?
C102 C103 1.366(4) . ?
C102 H102 0.9500 . ?
C103 C106 1.422(4) . ?
C103 C104 1.477(4) . ?
C104 C105 1.411(4) . ?
C105 C113 1.480(4) . ?
C107 C108 1.379(4) . ?
C107 C112 1.391(4) . ?
C108 C109 1.399(4) . ?
C109 C110 1.373(5) . ?
C109 H109 0.9500 . ?
C110 C111 1.391(5) . ?
C110 H110 0.9500 . ?
C111 C112 1.406(4) . ?
C111 H111 0.9500 . ?
C112 H112 0.9500 . ?
C113 C118 1.400(4) . ?
C113 C114 1.401(4) . ?
C114 C115 1.414(4) . ?
C115 C116 1.372(4) . ?
C115 H115 0.9500 . ?
C116 C117 1.377(4) . ?
C116 H116 0.9500 . ?
C117 C118 1.366(4) . ?
C117 H117 0.9500 . ?
C118 H118 0.9500 . ?
Cl1 C119 1.778(4) . ?
Cl2 C119 1.735(4) . ?
C119 H119 0.9900 . ?
C119 H120 0.9900 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N62 0.97(5) 1.85(5) 2.804(3) 166(4) 1_455 yes
O2 H2 N1 0.84 1.91 2.639(3) 144.0 . yes
O3 H3 N92 0.96(5) 1.78(5) 2.704(3) 162(4) 1_645 yes
O4 H4 N31 0.82(5) 1.88(5) 2.637(3) 153(6) . yes
O5 H5 N2 0.98(5) 1.85(5) 2.805(3) 167(4) . yes
O6 H6 N61 0.84 1.98 2.691(3) 142.4 . yes
O7 H7 N32 0.82(4) 1.98(4) 2.771(3) 160(3) 1_565 yes
O8 H8 N91 0.84 1.95 2.664(3) 141.9 . yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N1 N2 C3 -1.7(4) . . . . ?
N1 N2 C3 C4 0.4(4) . . . . ?
N1 N2 C3 C17 178.9(2) . . . . ?
N2 C3 C4 C14 3.2(4) . . . . ?
C17 C3 C4 C14 -175.2(2) . . . . ?
N2 C3 C4 C5 179.2(2) . . . . ?
C17 C3 C4 C5 0.7(4) . . . . ?
C3 C4 C5 C6 4.0(5) . . . . ?
C14 C4 C5 C6 -179.8(3) . . . . ?
C3 C4 C5 C16 -173.8(3) . . . . ?
C14 C4 C5 C16 2.5(3) . . . . ?
C16 C5 C6 C7 -2.6(4) . . . . ?
C4 C5 C6 C7 179.9(3) . . . . ?
C5 C6 C7 C8 3.5(4) . . . . ?
C6 C7 C8 C9 -0.9(4) . . . . ?
C7 C8 C9 C16 -2.4(4) . . . . ?
C7 C8 C9 C10 175.8(3) . . . . ?
C16 C9 C10 C11 1.5(4) . . . . ?
C8 C9 C10 C11 -176.8(3) . . . . ?
C9 C10 C11 C12 -2.9(4) . . . . ?
C10 C11 C12 C13 0.8(4) . . . . ?
C11 C12 C13 C16 2.6(3) . . . . ?
C11 C12 C13 C14 176.0(3) . . . . ?
C3 C4 C14 C15 -5.3(3) . . . . ?
C5 C4 C14 C15 177.9(2) . . . . ?
C3 C4 C14 C13 173.0(2) . . . . ?
C5 C4 C14 C13 -3.7(3) . . . . ?
C12 C13 C14 C15 7.4(5) . . . . ?
C16 C13 C14 C15 -178.6(3) . . . . ?
C12 C13 C14 C4 -170.5(3) . . . . ?
C16 C13 C14 C4 3.5(3) . . . . ?
N2 N1 C15 C14 -0.6(4) . . . . ?
N2 N1 C15 C23 -178.6(2) . . . . ?
C4 C14 C15 N1 4.1(3) . . . . ?
C13 C14 C15 N1 -173.6(3) . . . . ?
C4 C14 C15 C23 -178.2(2) . . . . ?
C13 C14 C15 C23 4.1(5) . . . . ?
C8 C9 C16 C5 3.4(4) . . . . ?
C10 C9 C16 C5 -175.1(2) . . . . ?
C8 C9 C16 C13 -179.4(2) . . . . ?
C10 C9 C16 C13 2.1(4) . . . . ?
C6 C5 C16 C9 -0.9(4) . . . . ?
C4 C5 C16 C9 177.3(2) . . . . ?
C6 C5 C16 C13 -178.4(2) . . . . ?
C4 C5 C16 C13 -0.2(3) . . . . ?
C12 C13 C16 C9 -4.2(4) . . . . ?
C14 C13 C16 C9 -179.5(2) . . . . ?
C12 C13 C16 C5 173.3(2) . . . . ?
C14 C13 C16 C5 -2.0(3) . . . . ?
N2 C3 C17 C18 -84.1(3) . . . . ?
C4 C3 C17 C18 94.4(3) . . . . ?
N2 C3 C17 C22 96.8(3) . . . . ?
C4 C3 C17 C22 -84.7(3) . . . . ?
C22 C17 C18 O1 177.8(2) . . . . ?
C3 C17 C18 O1 -1.4(4) . . . . ?
C22 C17 C18 C19 -0.1(4) . . . . ?
C3 C17 C18 C19 -179.3(2) . . . . ?
O1 C18 C19 C20 -177.0(2) . . . . ?
C17 C18 C19 C20 0.9(4) . . . . ?
C18 C19 C20 C21 -1.0(4) . . . . ?
C19 C20 C21 C22 0.3(5) . . . . ?
C20 C21 C22 C17 0.5(5) . . . . ?
C18 C17 C22 C21 -0.5(4) . . . . ?
C3 C17 C22 C21 178.6(3) . . . . ?
N1 C15 C23 C28 -148.3(3) . . . . ?
C14 C15 C23 C28 33.9(4) . . . . ?
N1 C15 C23 C24 31.4(4) . . . . ?
C14 C15 C23 C24 -146.4(3) . . . . ?
C28 C23 C24 O2 175.6(3) . . . . ?
C15 C23 C24 O2 -4.1(4) . . . . ?
C28 C23 C24 C25 -6.9(4) . . . . ?
C15 C23 C24 C25 173.5(3) . . . . ?
O2 C24 C25 C26 -177.2(3) . . . . ?
C23 C24 C25 C26 5.1(5) . . . . ?
C24 C25 C26 C27 -0.3(5) . . . . ?
C25 C26 C27 C28 -2.6(5) . . . . ?
C26 C27 C28 C23 0.7(5) . . . . ?
C24 C23 C28 C27 4.0(4) . . . . ?
C15 C23 C28 C27 -176.3(3) . . . . ?
C45 N31 N32 C33 -4.6(4) . . . . ?
N31 N32 C33 C34 3.9(4) . . . . ?
N31 N32 C33 C47 178.8(2) . . . . ?
N32 C33 C34 C44 2.3(4) . . . . ?
C47 C33 C34 C44 -172.1(2) . . . . ?
N32 C33 C34 C35 175.4(2) . . . . ?
C47 C33 C34 C35 1.0(4) . . . . ?
C33 C34 C35 C36 12.5(5) . . . . ?
C44 C34 C35 C36 -173.8(3) . . . . ?
C33 C34 C35 C46 -169.2(3) . . . . ?
C44 C34 C35 C46 4.5(3) . . . . ?
C46 C35 C36 C37 2.0(4) . . . . ?
C34 C35 C36 C37 -179.8(3) . . . . ?
C35 C36 C37 C38 0.5(4) . . . . ?
C36 C37 C38 C39 -2.2(4) . . . . ?
C37 C38 C39 C46 1.3(4) . . . . ?
C37 C38 C39 C40 -176.1(3) . . . . ?
C46 C39 C40 C41 0.1(4) . . . . ?
C38 C39 C40 C41 177.6(3) . . . . ?
C39 C40 C41 C42 0.3(4) . . . . ?
C40 C41 C42 C43 -1.8(4) . . . . ?
C41 C42 C43 C46 2.9(4) . . . . ?
C41 C42 C43 C44 -179.9(3) . . . . ?
C33 C34 C44 C45 -7.3(3) . . . . ?
C35 C34 C44 C45 178.2(2) . . . . ?
C33 C34 C44 C43 170.7(2) . . . . ?
C35 C34 C44 C43 -3.8(3) . . . . ?
C42 C43 C44 C34 -175.8(3) . . . . ?
C46 C43 C44 C34 1.6(3) . . . . ?
C42 C43 C44 C45 1.6(5) . . . . ?
C46 C43 C44 C45 179.0(3) . . . . ?
N32 N31 C45 C44 -0.8(4) . . . . ?
N32 N31 C45 C53 178.9(2) . . . . ?
C34 C44 C45 N31 6.6(3) . . . . ?
C43 C44 C45 N31 -170.6(3) . . . . ?
C34 C44 C45 C53 -173.1(2) . . . . ?
C43 C44 C45 C53 9.7(4) . . . . ?
C40 C39 C46 C35 178.9(2) . . . . ?
C38 C39 C46 C35 1.2(4) . . . . ?
C40 C39 C46 C43 1.2(4) . . . . ?
C38 C39 C46 C43 -176.6(2) . . . . ?
C36 C35 C46 C39 -2.9(4) . . . . ?
C34 C35 C46 C39 178.4(2) . . . . ?
C36 C35 C46 C43 175.1(2) . . . . ?
C34 C35 C46 C43 -3.6(3) . . . . ?
C42 C43 C46 C39 -2.7(4) . . . . ?
C44 C43 C46 C39 179.3(2) . . . . ?
C42 C43 C46 C35 179.3(2) . . . . ?
C44 C43 C46 C35 1.3(3) . . . . ?
N32 C33 C47 C52 -68.9(3) . . . . ?
C34 C33 C47 C52 105.8(3) . . . . ?
N32 C33 C47 C48 111.0(3) . . . . ?
C34 C33 C47 C48 -74.4(3) . . . . ?
C52 C47 C48 O3 -177.8(2) . . . . ?
C33 C47 C48 O3 2.4(4) . . . . ?
C52 C47 C48 C49 2.8(4) . . . . ?
C33 C47 C48 C49 -177.0(2) . . . . ?
O3 C48 C49 C50 178.8(3) . . . . ?
C47 C48 C49 C50 -1.9(4) . . . . ?
C48 C49 C50 C51 0.0(4) . . . . ?
C49 C50 C51 C52 0.9(4) . . . . ?
C48 C47 C52 C51 -2.0(4) . . . . ?
C33 C47 C52 C51 177.9(2) . . . . ?
C50 C51 C52 C47 0.1(4) . . . . ?
N31 C45 C53 C58 -146.9(3) . . . . ?
C44 C45 C53 C58 32.8(4) . . . . ?
N31 C45 C53 C54 29.9(3) . . . . ?
C44 C45 C53 C54 -150.4(3) . . . . ?
C58 C53 C54 O4 176.7(3) . . . . ?
C45 C53 C54 O4 -0.2(4) . . . . ?
C58 C53 C54 C55 -4.3(4) . . . . ?
C45 C53 C54 C55 178.9(2) . . . . ?
O4 C54 C55 C56 -177.0(3) . . . . ?
C53 C54 C55 C56 3.9(4) . . . . ?
C54 C55 C56 C57 -1.1(5) . . . . ?
C55 C56 C57 C58 -1.3(5) . . . . ?
C56 C57 C58 C53 0.8(5) . . . . ?
C54 C53 C58 C57 1.9(4) . . . . ?
C45 C53 C58 C57 178.8(3) . . . . ?
C75 N61 N62 C63 -1.6(3) . . . . ?
N61 N62 C63 C64 0.8(4) . . . . ?
N61 N62 C63 C77 179.3(2) . . . . ?
N62 C63 C64 C74 3.2(4) . . . . ?
C77 C63 C64 C74 -175.3(2) . . . . ?
N62 C63 C64 C65 175.8(2) . . . . ?
C77 C63 C64 C65 -2.7(4) . . . . ?
C63 C64 C65 C66 9.4(5) . . . . ?
C74 C64 C65 C66 -177.4(3) . . . . ?
C63 C64 C65 C76 -171.9(3) . . . . ?
C74 C64 C65 C76 1.3(3) . . . . ?
C76 C65 C66 C67 1.3(4) . . . . ?
C64 C65 C66 C67 179.9(3) . . . . ?
C65 C66 C67 C68 1.3(4) . . . . ?
C66 C67 C68 C69 -0.5(4) . . . . ?
C67 C68 C69 C76 -2.7(4) . . . . ?
C67 C68 C69 C70 175.5(3) . . . . ?
C76 C69 C70 C71 0.5(4) . . . . ?
C68 C69 C70 C71 -177.7(3) . . . . ?
C69 C70 C71 C72 -1.7(4) . . . . ?
C70 C71 C72 C73 0.4(4) . . . . ?
C71 C72 C73 C76 1.9(4) . . . . ?
C71 C72 C73 C74 174.1(3) . . . . ?
C63 C64 C74 C75 -6.1(3) . . . . ?
C65 C64 C74 C75 179.8(2) . . . . ?
C63 C64 C74 C73 171.5(2) . . . . ?
C65 C64 C74 C73 -2.6(3) . . . . ?
C72 C73 C74 C75 7.0(5) . . . . ?
C76 C73 C74 C75 179.7(3) . . . . ?
C72 C73 C74 C64 -169.9(3) . . . . ?
C76 C73 C74 C64 2.9(3) . . . . ?
N62 N61 C75 C74 -1.5(4) . . . . ?
N62 N61 C75 C83 177.8(2) . . . . ?
C64 C74 C75 N61 5.3(3) . . . . ?
C73 C74 C75 N61 -171.4(3) . . . . ?
C64 C74 C75 C83 -173.9(2) . . . . ?
C73 C74 C75 C83 9.4(4) . . . . ?
C68 C69 C76 C65 5.4(4) . . . . ?
C70 C69 C76 C65 -173.0(2) . . . . ?
C68 C69 C76 C73 -179.5(2) . . . . ?
C70 C69 C76 C73 2.1(4) . . . . ?
C66 C65 C76 C69 -4.8(4) . . . . ?
C64 C65 C76 C69 176.2(2) . . . . ?
C66 C65 C76 C73 179.5(2) . . . . ?
C64 C65 C76 C73 0.5(3) . . . . ?
C72 C73 C76 C69 -3.3(4) . . . . ?
C74 C73 C76 C69 -177.7(2) . . . . ?
C72 C73 C76 C65 172.3(2) . . . . ?
C74 C73 C76 C65 -2.1(3) . . . . ?
N62 C63 C77 C82 103.3(3) . . . . ?
C64 C63 C77 C82 -78.1(3) . . . . ?
N62 C63 C77 C78 -76.5(3) . . . . ?
C64 C63 C77 C78 102.0(3) . . . . ?
C82 C77 C78 O5 177.9(2) . . . . ?
C63 C77 C78 O5 -2.2(4) . . . . ?
C82 C77 C78 C79 0.7(4) . . . . ?
C63 C77 C78 C79 -179.5(2) . . . . ?
O5 C78 C79 C80 -176.4(3) . . . . ?
C77 C78 C79 C80 0.7(4) . . . . ?
C78 C79 C80 C81 -0.2(4) . . . . ?
C79 C80 C81 C82 -1.7(4) . . . . ?
C80 C81 C82 C77 3.2(5) . . . . ?
C78 C77 C82 C81 -2.6(4) . . . . ?
C63 C77 C82 C81 177.6(3) . . . . ?
N61 C75 C83 C88 -144.5(3) . . . . ?
C74 C75 C83 C88 34.7(4) . . . . ?
N61 C75 C83 C84 33.4(3) . . . . ?
C74 C75 C83 C84 -147.3(3) . . . . ?
C88 C83 C84 O6 178.9(3) . . . . ?
C75 C83 C84 O6 1.0(4) . . . . ?
C88 C83 C84 C85 -3.2(4) . . . . ?
C75 C83 C84 C85 178.8(3) . . . . ?
O6 C84 C85 C86 179.7(3) . . . . ?
C83 C84 C85 C86 1.7(5) . . . . ?
C84 C85 C86 C87 0.9(5) . . . . ?
C85 C86 C87 C88 -2.0(5) . . . . ?
C86 C87 C88 C83 0.5(5) . . . . ?
C84 C83 C88 C87 2.1(4) . . . . ?
C75 C83 C88 C87 -179.9(3) . . . . ?
C105 N91 N92 C93 -2.0(4) . . . . ?
N91 N92 C93 C94 5.2(4) . . . . ?
N91 N92 C93 C107 -178.3(2) . . . . ?
N92 C93 C94 C104 -0.6(4) . . . . ?
C107 C93 C94 C104 -176.8(2) . . . . ?
N92 C93 C94 C95 171.0(3) . . . . ?
C107 C93 C94 C95 -5.1(4) . . . . ?
C93 C94 C95 C96 13.3(5) . . . . ?
C104 C94 C95 C96 -174.4(3) . . . . ?
C93 C94 C95 C106 -168.9(3) . . . . ?
C104 C94 C95 C106 3.4(3) . . . . ?
C106 C95 C96 C97 3.8(4) . . . . ?
C94 C95 C96 C97 -178.6(3) . . . . ?
C95 C96 C97 C98 -0.1(4) . . . . ?
C96 C97 C98 C99 -3.1(4) . . . . ?
C97 C98 C99 C106 2.3(4) . . . . ?
C97 C98 C99 C100 -176.8(3) . . . . ?
C106 C99 C100 C101 -0.2(4) . . . . ?
C98 C99 C100 C101 179.0(3) . . . . ?
C99 C100 C101 C102 0.3(4) . . . . ?
C100 C101 C102 C103 -0.7(4) . . . . ?
C101 C102 C103 C106 1.1(4) . . . . ?
C101 C102 C103 C104 177.9(3) . . . . ?
C93 C94 C104 C105 -6.7(3) . . . . ?
C95 C94 C104 C105 179.8(2) . . . . ?
C93 C94 C104 C103 170.6(2) . . . . ?
C95 C94 C104 C103 -2.9(3) . . . . ?
C102 C103 C104 C94 -175.9(3) . . . . ?
C106 C103 C104 C94 1.2(3) . . . . ?
C102 C103 C104 C105 0.7(5) . . . . ?
C106 C103 C104 C105 177.8(3) . . . . ?
N92 N91 C105 C104 -5.8(4) . . . . ?
N92 N91 C105 C113 173.0(2) . . . . ?
C94 C104 C105 N91 9.9(3) . . . . ?
C103 C104 C105 N91 -166.5(3) . . . . ?
C94 C104 C105 C113 -168.8(2) . . . . ?
C103 C104 C105 C113 14.8(4) . . . . ?
C98 C99 C106 C95 1.5(4) . . . . ?
C100 C99 C106 C95 -179.3(2) . . . . ?
C98 C99 C106 C103 -178.7(2) . . . . ?
C100 C99 C106 C103 0.6(4) . . . . ?
C96 C95 C106 C99 -4.6(4) . . . . ?
C94 C95 C106 C99 177.2(2) . . . . ?
C96 C95 C106 C103 175.5(2) . . . . ?
C94 C95 C106 C103 -2.7(3) . . . . ?
C102 C103 C106 C99 -1.1(4) . . . . ?
C104 C103 C106 C99 -178.8(2) . . . . ?
C102 C103 C106 C95 178.8(2) . . . . ?
C104 C103 C106 C95 1.0(3) . . . . ?
N92 C93 C107 C108 114.5(3) . . . . ?
C94 C93 C107 C108 -69.1(4) . . . . ?
N92 C93 C107 C112 -63.5(3) . . . . ?
C94 C93 C107 C112 112.8(3) . . . . ?
C112 C107 C108 O7 178.3(3) . . . . ?
C93 C107 C108 O7 0.3(4) . . . . ?
C112 C107 C108 C109 0.0(4) . . . . ?
C93 C107 C108 C109 -178.0(3) . . . . ?
O7 C108 C109 C110 -178.1(3) . . . . ?
C107 C108 C109 C110 0.2(5) . . . . ?
C108 C109 C110 C111 0.2(5) . . . . ?
C109 C110 C111 C112 -0.7(5) . . . . ?
C108 C107 C112 C111 -0.5(4) . . . . ?
C93 C107 C112 C111 177.5(3) . . . . ?
C110 C111 C112 C107 0.8(5) . . . . ?
N91 C105 C113 C118 -145.0(2) . . . . ?
C104 C105 C113 C118 33.7(4) . . . . ?
N91 C105 C113 C114 32.4(3) . . . . ?
C104 C105 C113 C114 -148.9(3) . . . . ?
C118 C113 C114 O8 175.9(2) . . . . ?
C105 C113 C114 O8 -1.5(4) . . . . ?
C118 C113 C114 C115 -3.8(4) . . . . ?
C105 C113 C114 C115 178.7(2) . . . . ?
O8 C114 C115 C116 -178.4(3) . . . . ?
C113 C114 C115 C116 1.3(4) . . . . ?
C114 C115 C116 C117 2.0(5) . . . . ?
C115 C116 C117 C118 -2.8(5) . . . . ?
C116 C117 C118 C113 0.1(4) . . . . ?
C114 C113 C118 C117 3.1(4) . . . . ?
C105 C113 C118 C117 -179.4(3) . . . . ?
loop_
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1 PubChem 139190142
