#------------------------------------------------------------------------------
#$Date: 2025-08-22 23:12:46 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301866 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/07/7230722.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_7230722
loop_
_publ_author_name
'Wang, Dong'
'Li, Linna'
'Feng, Hairong'
'Sun, Hua'
'Almeida-Veloso, Fabrice'
'Charavin, Marine'
'Yu, Peng'
'Désaubry, Laurent'
_publ_section_title
;
 Catalyst-free three-component synthesis of highly functionalized
 2,3-dihydropyrroles
;
_journal_issue                   12
_journal_name_full               'Green Chemistry'
_journal_page_first              2775
_journal_paper_doi               10.1039/C8GC00987B
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C41 H35 Cl2 N3 O3, C4 H8 O, C3 H6'
_chemical_formula_sum            'C48 H49 Cl2 N3 O4'
_chemical_formula_weight         802.80
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-12-02
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2018-02-08 deposited with the CCDC.
2018-05-14 downloaded from the CCDC.
;
_cell_angle_alpha                98.819(9)
_cell_angle_beta                 97.641(6)
_cell_angle_gamma                98.079(5)
_cell_formula_units_Z            2
_cell_length_a                   12.043(3)
_cell_length_b                   13.174(4)
_cell_length_c                   13.616(4)
_cell_measurement_reflns_used    3214
_cell_measurement_temperature    113
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.1
_cell_volume                     2087.0(10)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      113
_diffrn_detector                 PILT
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details
;
scan:
    Number of images: 360
               Slice: -105.0000 - 75.0000
         Image width: 0.5000
            Exp time: 40.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 0.0000
                 XTD: 44.9752
              2theta: -15.0855
scan:
    Number of images: 360
               Slice: -105.0000 - 75.0000
         Image width: 0.5000
            Exp time: 40.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 90.0000
                 XTD: 44.9752
              2theta: -15.0855
scan:
    Number of images: 360
               Slice: -105.0000 - 75.0000
         Image width: 0.5000
            Exp time: 40.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 180.0000
                 XTD: 44.9752
              2theta: -15.0855
;
_diffrn_measurement_device
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Rigaku Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.022704
_diffrn_orient_matrix_UB_12      -0.001546
_diffrn_orient_matrix_UB_13      -0.081829
_diffrn_orient_matrix_UB_21      0.003085
_diffrn_orient_matrix_UB_22      0.076566
_diffrn_orient_matrix_UB_23      -0.013873
_diffrn_orient_matrix_UB_31      0.073900
_diffrn_orient_matrix_UB_32      0.011881
_diffrn_orient_matrix_UB_33      0.007941
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            26425
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.603
_diffrn_reflns_theta_min         3.067
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.411
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    "'not measured'"
_exptl_crystal_description       Prism
_exptl_crystal_F_000             848
_exptl_crystal_preparation       Fiber
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.777
_refine_diff_density_min         -0.738
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     523
_refine_ls_number_reflns         9393
_refine_ls_number_restraints     50
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0568
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0723P)²+1.1140P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1415
_refine_ls_wR_factor_ref         0.1572
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6643
_reflns_number_total             9393
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8gc00987b2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7230721--7230722.cif.
;
_cod_original_cell_volume        2086.9(11)
_cod_database_code               7230722
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.957
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-H1 = N3-H3
 0.9 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C42) \\sim Ueq, Uanis(C43) \\sim Ueq, Uanis(C44) \\sim Ueq, Uanis(C45)
\\sim Ueq, Uanis(C46) \\sim Ueq, Uanis(C47) \\sim Ueq, Uanis(C48) \\sim Ueq,
Uanis(O4) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4.a Ternary CH refined with riding coordinates:
 C10(H10)
4.b Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B), C42(H42A,H42B), C43(H43A,H43B), C44(H44A,H44B), C45(H45A,
 H45B), C46(H46A,H46B), C47(H47A,H47B), C48(H48A,H48B)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C4(H4), C6(H6), C12(H12), C13(H13), C15(H15), C16(H16),
 C22(H22), C23(H23), C24(H24), C26(H26), C29(H29), C30(H30), C31(H31), C32(H32),
  C33(H33), C36(H36), C37(H37), C39(H39), C40(H40)
4.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C41(H41A,H41B,H41C)
;
_shelx_shelxl_version_number     2014/8
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Cl1 Cl 1.06924(5) 0.40908(6) 0.06734(5) 0.04782(19) Uani 1 1 d . .
Cl2 Cl 0.37451(7) 0.16010(6) 0.97118(8) 0.0708(3) Uani 1 1 d . .
O1 O 0.81712(12) 0.46860(10) 0.33123(11) 0.0244(3) Uani 1 1 d . .
O2 O 0.54845(12) 0.40750(11) 0.34057(10) 0.0228(3) Uani 1 1 d . .
O3 O 0.64573(13) 0.30488(12) 0.76696(12) 0.0324(4) Uani 1 1 d . .
N1 N 0.70878(14) 0.32576(13) 0.22579(13) 0.0220(4) Uani 1 1 d D .
H1 H 0.6470(13) 0.2788(14) 0.2235(18) 0.026 Uiso 1 1 d DR .
N2 N 0.76964(14) 0.37848(12) 0.63318(12) 0.0203(3) Uani 1 1 d . .
N3 N 0.54032(15) 0.43594(13) 0.77702(13) 0.0227(4) Uani 1 1 d D .
H3 H 0.526(2) 0.4904(13) 0.7481(16) 0.027 Uiso 1 1 d DR .
C1 C 0.76733(17) 0.31647(15) 0.14296(15) 0.0223(4) Uani 1 1 d . .
C2 C 0.70889(19) 0.25593(17) 0.05276(17) 0.0303(5) Uani 1 1 d . .
H2 H 0.6330 0.2224 0.0495 0.036 Uiso 1 1 calc R .
C3 C 0.7614(2) 0.24478(19) -0.03164(17) 0.0352(5) Uani 1 1 d . .
H3A H 0.7208 0.2041 -0.0929 0.042 Uiso 1 1 calc R .
C4 C 0.8723(2) 0.29216(19) -0.02820(17) 0.0331(5) Uani 1 1 d . .
H4 H 0.9085 0.2847 -0.0861 0.040 Uiso 1 1 calc R .
C5 C 0.92838(19) 0.35059(18) 0.06200(17) 0.0296(5) Uani 1 1 d . .
C6 C 0.87925(18) 0.36399(17) 0.14788(16) 0.0269(4) Uani 1 1 d . .
H6 H 0.9206 0.4046 0.2088 0.032 Uiso 1 1 calc R .
C7 C 0.73541(16) 0.39829(15) 0.31115(14) 0.0195(4) Uani 1 1 d . .
C8 C 0.64341(16) 0.39153(14) 0.37878(15) 0.0188(4) Uani 1 1 d . .
C9 C 0.66939(16) 0.38155(14) 0.48076(15) 0.0197(4) Uani 1 1 d . .
C10 C 0.58745(16) 0.40028(15) 0.55427(14) 0.0196(4) Uani 1 1 d . .
H10 H 0.5513 0.4618 0.5414 0.024 Uiso 1 1 calc R .
C11 C 0.49467(17) 0.30691(15) 0.54984(15) 0.0216(4) Uani 1 1 d . .
C12 C 0.5153(2) 0.20524(18) 0.5351(2) 0.0361(5) Uani 1 1 d . .
H12 H 0.5882 0.1917 0.5231 0.043 Uiso 1 1 calc R .
C13 C 0.4306(2) 0.12299(18) 0.5377(2) 0.0429(6) Uani 1 1 d . .
H13 H 0.4467 0.0540 0.5263 0.051 Uiso 1 1 calc R .
C14 C 0.3236(2) 0.13851(17) 0.55636(18) 0.0333(5) Uani 1 1 d . .
C15 C 0.30305(19) 0.24002(17) 0.57174(18) 0.0313(5) Uani 1 1 d . .
H15 H 0.2305 0.2534 0.5851 0.038 Uiso 1 1 calc R .
C16 C 0.38716(18) 0.32285(16) 0.56791(17) 0.0270(5) Uani 1 1 d . .
H16 H 0.3706 0.3917 0.5779 0.032 Uiso 1 1 calc R .
C17 C 0.2330(2) 0.0483(2) 0.5608(3) 0.0510(7) Uani 1 1 d . .
H17A H 0.2444 -0.0140 0.5162 0.077 Uiso 1 1 calc GR .
H17B H 0.1580 0.0653 0.5391 0.077 Uiso 1 1 calc GR .
H17C H 0.2379 0.0350 0.6300 0.077 Uiso 1 1 calc GR .
C18 C 0.67166(16) 0.42999(15) 0.65690(15) 0.0203(4) Uani 1 1 d . .
C19 C 0.71202(18) 0.54771(15) 0.68337(16) 0.0240(4) Uani 1 1 d . .
H19A H 0.7673 0.5639 0.7455 0.036 Uiso 1 1 calc GR .
H19B H 0.6469 0.5831 0.6930 0.036 Uiso 1 1 calc GR .
H19C H 0.7477 0.5716 0.6285 0.036 Uiso 1 1 calc GR .
C20 C 0.61944(17) 0.38350(15) 0.74023(15) 0.0219(4) Uani 1 1 d . .
C21 C 0.46771(17) 0.40450(17) 0.84450(15) 0.0244(4) Uani 1 1 d . .
C22 C 0.4033(2) 0.47574(19) 0.88334(17) 0.0328(5) Uani 1 1 d . .
H22 H 0.4095 0.5428 0.8649 0.039 Uiso 1 1 calc R .
C23 C 0.3301(2) 0.4493(2) 0.9489(2) 0.0422(6) Uani 1 1 d . .
H23 H 0.2858 0.4983 0.9747 0.051 Uiso 1 1 calc R .
C24 C 0.3206(2) 0.3528(2) 0.9772(2) 0.0446(7) Uani 1 1 d . .
H24 H 0.2707 0.3345 1.0225 0.054 Uiso 1 1 calc R .
C25 C 0.3855(2) 0.2839(2) 0.9379(2) 0.0395(6) Uani 1 1 d . .
C26 C 0.45898(19) 0.30716(18) 0.87165(18) 0.0329(5) Uani 1 1 d . .
H26 H 0.5023 0.2575 0.8454 0.039 Uiso 1 1 calc R .
C27 C 0.86858(17) 0.38736(15) 0.71182(15) 0.0223(4) Uani 1 1 d . .
H27A H 0.8450 0.4070 0.7781 0.027 Uiso 1 1 calc R .
H27B H 0.9269 0.4448 0.7032 0.027 Uiso 1 1 calc R .
C28 C 0.92249(18) 0.29074(16) 0.71337(15) 0.0233(4) Uani 1 1 d . .
C29 C 1.03937(19) 0.30231(19) 0.74240(18) 0.0321(5) Uani 1 1 d . .
H29 H 1.0842 0.3697 0.7554 0.039 Uiso 1 1 calc R .
C30 C 1.0906(2) 0.2158(2) 0.7525(2) 0.0439(6) Uani 1 1 d . .
H30 H 1.1704 0.2240 0.7725 0.053 Uiso 1 1 calc R .
C31 C 1.0261(2) 0.1185(2) 0.7334(2) 0.0481(7) Uani 1 1 d . .
H31 H 1.0612 0.0594 0.7410 0.058 Uiso 1 1 calc R .
C32 C 0.9095(2) 0.1061(2) 0.7032(2) 0.0444(6) Uani 1 1 d . .
H32 H 0.8654 0.0383 0.6888 0.053 Uiso 1 1 calc R .
C33 C 0.8574(2) 0.19224(17) 0.69390(18) 0.0308(5) Uani 1 1 d . .
H33 H 0.7775 0.1838 0.6743 0.037 Uiso 1 1 calc R .
C34 C 0.76984(16) 0.36289(14) 0.53256(14) 0.0189(4) Uani 1 1 d . .
C35 C 0.86291(16) 0.32344(14) 0.48573(14) 0.0192(4) Uani 1 1 d . .
C36 C 0.97556(17) 0.37252(15) 0.51102(15) 0.0208(4) Uani 1 1 d . .
H36 H 0.9959 0.4320 0.5629 0.025 Uiso 1 1 calc R .
C37 C 1.05804(17) 0.33489(15) 0.46075(16) 0.0233(4) Uani 1 1 d . .
H37 H 1.1346 0.3691 0.4787 0.028 Uiso 1 1 calc R .
C38 C 1.03112(18) 0.24803(15) 0.38447(16) 0.0250(4) Uani 1 1 d . .
C39 C 0.91830(18) 0.19821(15) 0.36065(16) 0.0263(4) Uani 1 1 d . .
H39 H 0.8983 0.1381 0.3096 0.032 Uiso 1 1 calc R .
C40 C 0.83515(17) 0.23516(14) 0.41039(15) 0.0218(4) Uani 1 1 d . .
H40 H 0.7588 0.2003 0.3932 0.026 Uiso 1 1 calc R .
C41 C 1.1205(2) 0.20846(18) 0.3283(2) 0.0364(5) Uani 1 1 d . .
H41A H 1.1254 0.2421 0.2693 0.055 Uiso 1 1 calc GR .
H41B H 1.1002 0.1329 0.3066 0.055 Uiso 1 1 calc GR .
H41C H 1.1942 0.2246 0.3727 0.055 Uiso 1 1 calc GR .
O4 O 0.53278(17) 0.16259(15) 0.2371(2) 0.0669(7) Uani 1 1 d . U
C42 C 0.4175(2) 0.1655(2) 0.2530(2) 0.0506(7) Uani 1 1 d . U
H42A H 0.3765 0.1964 0.2001 0.061 Uiso 1 1 calc R .
H42B H 0.4156 0.2073 0.3195 0.061 Uiso 1 1 calc R .
C43 C 0.3644(3) 0.0539(2) 0.2481(3) 0.0621(9) Uani 1 1 d . U
H43A H 0.3576 0.0390 0.3163 0.074 Uiso 1 1 calc R .
H43B H 0.2881 0.0385 0.2066 0.074 Uiso 1 1 calc R .
C44 C 0.4427(4) -0.0079(3) 0.2013(4) 0.0914(13) Uani 1 1 d . U
H44A H 0.4466 -0.0719 0.2305 0.110 Uiso 1 1 calc R .
H44B H 0.4175 -0.0279 0.1277 0.110 Uiso 1 1 calc R .
C45 C 0.5526(3) 0.0595(3) 0.2228(5) 0.1001(16) Uani 1 1 d . U
H45A H 0.5978 0.0457 0.2841 0.120 Uiso 1 1 calc R .
H45B H 0.5951 0.0466 0.1660 0.120 Uiso 1 1 calc R .
C46 C 0.8843(3) 0.0120(3) -0.0008(4) 0.0825(12) Uani 1 1 d . U
H46A H 0.8703 0.0486 -0.0585 0.099 Uiso 1 1 calc R .
H46B H 0.8126 0.0004 0.0271 0.099 Uiso 1 1 calc R .
C47 C 0.9735(3) 0.0797(2) 0.0781(3) 0.0578(8) Uani 1 1 d . U
H47A H 0.9510 0.1487 0.0965 0.069 Uiso 1 1 calc R .
H47B H 0.9823 0.0476 0.1393 0.069 Uiso 1 1 calc R .
C48 C 1.0832(3) 0.0920(2) 0.0379(3) 0.0638(9) Uani 1 1 d . U
H48A H 1.1440 0.1324 0.0915 0.077 Uiso 1 1 calc R .
H48B H 1.0763 0.1317 -0.0182 0.077 Uiso 1 1 calc R .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C1 N1 H1 117.6(15) . .
C7 N1 H1 114.7(15) . .
C7 N1 C1 127.61(17) . .
C27 N2 C18 119.42(16) . .
C34 N2 C18 109.75(15) . .
C34 N2 C27 126.28(16) . .
C20 N3 H3 115.6(16) . .
C20 N3 C21 126.56(17) . .
C21 N3 H3 117.1(16) . .
C2 C1 N1 117.33(18) . .
C6 C1 N1 122.94(18) . .
C6 C1 C2 119.73(19) . .
C1 C2 H2 120.0 . .
C3 C2 C1 120.1(2) . .
C3 C2 H2 120.0 . .
C2 C3 H3A 119.6 . .
C2 C3 C4 120.9(2) . .
C4 C3 H3A 119.6 . .
C3 C4 H4 121.1 . .
C5 C4 C3 117.9(2) . .
C5 C4 H4 121.1 . .
C4 C5 Cl1 118.08(17) . .
C6 C5 Cl1 118.74(17) . .
C6 C5 C4 123.2(2) . .
C1 C6 H6 120.9 . .
C5 C6 C1 118.3(2) . .
C5 C6 H6 120.9 . .
O1 C7 N1 126.02(18) . .
O1 C7 C8 121.21(17) . .
N1 C7 C8 112.47(16) . .
O2 C8 C7 115.11(17) . .
O2 C8 C9 122.93(18) . .
C9 C8 C7 121.47(17) . .
C8 C9 C10 121.83(17) . .
C34 C9 C8 129.07(18) . .
C34 C9 C10 108.92(16) . .
C9 C10 H10 109.2 . .
C9 C10 C11 113.92(16) . .
C9 C10 C18 100.86(15) . .
C11 C10 H10 109.2 . .
C11 C10 C18 114.00(15) . .
C18 C10 H10 109.2 . .
C12 C11 C10 122.43(19) . .
C12 C11 C16 117.54(19) . .
C16 C11 C10 119.88(18) . .
C11 C12 H12 119.7 . .
C11 C12 C13 120.7(2) . .
C13 C12 H12 119.7 . .
C12 C13 H13 119.0 . .
C14 C13 C12 122.0(2) . .
C14 C13 H13 119.0 . .
C13 C14 C15 117.4(2) . .
C13 C14 C17 121.3(2) . .
C15 C14 C17 121.3(2) . .
C14 C15 H15 119.5 . .
C14 C15 C16 120.9(2) . .
C16 C15 H15 119.5 . .
C11 C16 C15 121.4(2) . .
C11 C16 H16 119.3 . .
C15 C16 H16 119.3 . .
C14 C17 H17A 109.5 . .
C14 C17 H17B 109.5 . .
C14 C17 H17C 109.5 . .
H17A C17 H17B 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
N2 C18 C10 102.34(15) . .
N2 C18 C19 108.63(15) . .
N2 C18 C20 109.67(15) . .
C19 C18 C10 111.00(16) . .
C19 C18 C20 113.79(16) . .
C20 C18 C10 110.78(15) . .
C18 C19 H19A 109.5 . .
C18 C19 H19B 109.5 . .
C18 C19 H19C 109.5 . .
H19A C19 H19B 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
O3 C20 N3 124.60(19) . .
O3 C20 C18 121.68(18) . .
N3 C20 C18 113.68(17) . .
C22 C21 N3 117.34(19) . .
C26 C21 N3 122.73(19) . .
C26 C21 C22 119.9(2) . .
C21 C22 H22 120.0 . .
C23 C22 C21 120.0(2) . .
C23 C22 H22 120.0 . .
C22 C23 H23 119.6 . .
C24 C23 C22 120.9(2) . .
C24 C23 H23 119.6 . .
C23 C24 H24 121.1 . .
C25 C24 C23 117.9(2) . .
C25 C24 H24 121.1 . .
C24 C25 Cl2 119.12(19) . .
C24 C25 C26 122.9(2) . .
C26 C25 Cl2 117.9(2) . .
C21 C26 C25 118.3(2) . .
C21 C26 H26 120.8 . .
C25 C26 H26 120.8 . .
N2 C27 H27A 108.4 . .
N2 C27 H27B 108.4 . .
N2 C27 C28 115.69(16) . .
H27A C27 H27B 107.4 . .
C28 C27 H27A 108.4 . .
C28 C27 H27B 108.4 . .
C29 C28 C27 118.59(19) . .
C33 C28 C27 121.47(19) . .
C33 C28 C29 119.8(2) . .
C28 C29 H29 119.9 . .
C30 C29 C28 120.2(2) . .
C30 C29 H29 119.9 . .
C29 C30 H30 120.0 . .
C31 C30 C29 120.0(2) . .
C31 C30 H30 120.0 . .
C30 C31 H31 119.9 . .
C30 C31 C32 120.2(2) . .
C32 C31 H31 119.9 . .
C31 C32 H32 119.9 . .
C33 C32 C31 120.2(2) . .
C33 C32 H32 119.9 . .
C28 C33 H33 120.2 . .
C32 C33 C28 119.7(2) . .
C32 C33 H33 120.2 . .
N2 C34 C9 111.41(17) . .
N2 C34 C35 123.02(17) . .
C9 C34 C35 125.42(17) . .
C36 C35 C34 122.86(17) . .
C36 C35 C40 119.02(18) . .
C40 C35 C34 118.08(17) . .
C35 C36 H36 119.9 . .
C37 C36 C35 120.14(18) . .
C37 C36 H36 119.9 . .
C36 C37 H37 119.3 . .
C36 C37 C38 121.36(19) . .
C38 C37 H37 119.3 . .
C37 C38 C39 118.17(19) . .
C37 C38 C41 121.32(19) . .
C39 C38 C41 120.51(19) . .
C38 C39 H39 119.5 . .
C40 C39 C38 120.95(19) . .
C40 C39 H39 119.5 . .
C35 C40 H40 119.8 . .
C39 C40 C35 120.34(19) . .
C39 C40 H40 119.8 . .
C38 C41 H41A 109.5 . .
C38 C41 H41B 109.5 . .
C38 C41 H41C 109.5 . .
H41A C41 H41B 109.5 . .
H41A C41 H41C 109.5 . .
H41B C41 H41C 109.5 . .
C45 O4 C42 110.0(2) . .
O4 C42 H42A 110.6 . .
O4 C42 H42B 110.6 . .
O4 C42 C43 105.8(2) . .
H42A C42 H42B 108.7 . .
C43 C42 H42A 110.6 . .
C43 C42 H42B 110.6 . .
C42 C43 H43A 110.8 . .
C42 C43 H43B 110.8 . .
H43A C43 H43B 108.9 . .
C44 C43 C42 104.6(3) . .
C44 C43 H43A 110.8 . .
C44 C43 H43B 110.8 . .
C43 C44 H44A 110.6 . .
C43 C44 H44B 110.6 . .
H44A C44 H44B 108.8 . .
C45 C44 C43 105.5(3) . .
C45 C44 H44A 110.6 . .
C45 C44 H44B 110.6 . .
O4 C45 C44 107.5(3) . .
O4 C45 H45A 110.2 . .
O4 C45 H45B 110.2 . .
C44 C45 H45A 110.2 . .
C44 C45 H45B 110.2 . .
H45A C45 H45B 108.5 . .
H46A C46 H46B 107.8 . .
C47 C46 H46A 109.0 . .
C47 C46 H46B 109.0 . .
C47 C46 C48 112.8(3) . 2_755
C48 C46 H46A 109.0 2_755 .
C48 C46 H46B 109.0 2_755 .
C46 C47 H47A 109.9 . .
C46 C47 H47B 109.9 . .
H47A C47 H47B 108.3 . .
C48 C47 C46 108.9(3) . .
C48 C47 H47A 109.9 . .
C48 C47 H47B 109.9 . .
C46 C48 H48A 109.3 2_755 .
C46 C48 H48B 109.3 2_755 .
C47 C48 C46 111.6(3) . 2_755
C47 C48 H48A 109.3 . .
C47 C48 H48B 109.3 . .
H48A C48 H48B 108.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C5 1.749(2) .
Cl2 C25 1.750(3) .
O1 C7 1.223(2) .
O2 C8 1.251(2) .
O3 C20 1.218(2) .
N1 H1 0.892(10) .
N1 C1 1.406(3) .
N1 C7 1.357(3) .
N2 C18 1.489(2) .
N2 C27 1.471(3) .
N2 C34 1.354(3) .
N3 H3 0.897(10) .
N3 C20 1.357(3) .
N3 C21 1.417(3) .
C1 C2 1.397(3) .
C1 C6 1.392(3) .
C2 H2 0.9500 .
C2 C3 1.382(3) .
C3 H3A 0.9500 .
C3 C4 1.384(3) .
C4 H4 0.9500 .
C4 C5 1.379(3) .
C5 C6 1.378(3) .
C6 H6 0.9500 .
C7 C8 1.534(3) .
C8 C9 1.413(3) .
C9 C10 1.514(3) .
C9 C34 1.390(3) .
C10 H10 1.0000 .
C10 C11 1.529(3) .
C10 C18 1.574(3) .
C11 C12 1.386(3) .
C11 C16 1.388(3) .
C12 H12 0.9500 .
C12 C13 1.388(3) .
C13 H13 0.9500 .
C13 C14 1.383(3) .
C14 C15 1.384(3) .
C14 C17 1.511(3) .
C15 H15 0.9500 .
C15 C16 1.393(3) .
C16 H16 0.9500 .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C18 C19 1.530(3) .
C18 C20 1.534(3) .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
C21 C22 1.387(3) .
C21 C26 1.382(3) .
C22 H22 0.9500 .
C22 C23 1.383(3) .
C23 H23 0.9500 .
C23 C24 1.378(4) .
C24 H24 0.9500 .
C24 C25 1.373(4) .
C25 C26 1.383(3) .
C26 H26 0.9500 .
C27 H27A 0.9900 .
C27 H27B 0.9900 .
C27 C28 1.510(3) .
C28 C29 1.391(3) .
C28 C33 1.386(3) .
C29 H29 0.9500 .
C29 C30 1.386(3) .
C30 H30 0.9500 .
C30 C31 1.371(4) .
C31 H31 0.9500 .
C31 C32 1.389(4) .
C32 H32 0.9500 .
C32 C33 1.386(3) .
C33 H33 0.9500 .
C34 C35 1.478(3) .
C35 C36 1.392(3) .
C35 C40 1.397(3) .
C36 H36 0.9500 .
C36 C37 1.384(3) .
C37 H37 0.9500 .
C37 C38 1.391(3) .
C38 C39 1.396(3) .
C38 C41 1.507(3) .
C39 H39 0.9500 .
C39 C40 1.384(3) .
C40 H40 0.9500 .
C41 H41A 0.9800 .
C41 H41B 0.9800 .
C41 H41C 0.9800 .
O4 C42 1.437(3) .
O4 C45 1.401(4) .
C42 H42A 0.9900 .
C42 H42B 0.9900 .
C42 C43 1.506(4) .
C43 H43A 0.9900 .
C43 H43B 0.9900 .
C43 C44 1.475(5) .
C44 H44A 0.9900 .
C44 H44B 0.9900 .
C44 C45 1.453(5) .
C45 H45A 0.9900 .
C45 H45B 0.9900 .
C46 H46A 0.9900 .
C46 H46B 0.9900 .
C46 C47 1.495(5) .
C46 C48 1.509(5) 2_755
C47 H47A 0.9900 .
C47 H47B 0.9900 .
C47 C48 1.494(5) .
C48 C46 1.509(5) 2_755
C48 H48A 0.9900 .
C48 H48B 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
N1 H1 O4 0.892(10) 1.958(11) 2.836(3) 168(2) .
N3 H3 O2 0.897(10) 2.148(11) 3.023(2) 165(2) 2_666
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_4
Cl1 C5 C6 C1 -179.55(16) . .
Cl2 C25 C26 C21 179.61(19) . .
O1 C7 C8 O2 111.9(2) . .
O1 C7 C8 C9 -60.2(3) . .
O2 C8 C9 C10 -6.3(3) . .
O2 C8 C9 C34 179.30(18) . .
N1 C1 C2 C3 179.3(2) . .
N1 C1 C6 C5 -179.5(2) . .
N1 C7 C8 O2 -62.1(2) . .
N1 C7 C8 C9 125.75(19) . .
N2 C18 C20 O3 -11.3(3) . .
N2 C18 C20 N3 170.88(16) . .
N2 C27 C28 C29 146.54(19) . .
N2 C27 C28 C33 -38.3(3) . .
N2 C34 C35 C36 -56.9(3) . .
N2 C34 C35 C40 125.5(2) . .
N3 C21 C22 C23 179.4(2) . .
N3 C21 C26 C25 -179.9(2) . .
C1 N1 C7 O1 -0.8(3) . .
C1 N1 C7 C8 172.89(18) . .
C1 C2 C3 C4 0.6(4) . .
C2 C1 C6 C5 0.9(3) . .
C2 C3 C4 C5 0.0(4) . .
C3 C4 C5 Cl1 179.07(18) . .
C3 C4 C5 C6 -0.2(4) . .
C4 C5 C6 C1 -0.3(3) . .
C6 C1 C2 C3 -1.1(3) . .
C7 N1 C1 C2 -162.2(2) . .
C7 N1 C1 C6 18.1(3) . .
C7 C8 C9 C10 165.23(17) . .
C7 C8 C9 C34 -9.2(3) . .
C8 C9 C10 C11 82.1(2) . .
C8 C9 C10 C18 -155.34(17) . .
C8 C9 C34 N2 168.06(18) . .
C8 C9 C34 C35 -16.3(3) . .
C9 C10 C11 C12 38.1(3) . .
C9 C10 C11 C16 -146.48(19) . .
C9 C10 C18 N2 -24.74(17) . .
C9 C10 C18 C19 90.99(17) . .
C9 C10 C18 C20 -141.58(15) . .
C9 C34 C35 C36 127.9(2) . .
C9 C34 C35 C40 -49.7(3) . .
C10 C9 C34 N2 -6.9(2) . .
C10 C9 C34 C35 168.74(17) . .
C10 C11 C12 C13 176.0(2) . .
C10 C11 C16 C15 -175.3(2) . .
C10 C18 C20 O3 100.9(2) . .
C10 C18 C20 N3 -76.9(2) . .
C11 C10 C18 N2 97.77(18) . .
C11 C10 C18 C19 -146.50(17) . .
C11 C10 C18 C20 -19.1(2) . .
C11 C12 C13 C14 -1.0(4) . .
C12 C11 C16 C15 0.4(3) . .
C12 C13 C14 C15 0.5(4) . .
C12 C13 C14 C17 -178.9(3) . .
C13 C14 C15 C16 0.3(4) . .
C14 C15 C16 C11 -0.8(4) . .
C16 C11 C12 C13 0.5(4) . .
C17 C14 C15 C16 179.7(2) . .
C18 N2 C27 C28 141.54(17) . .
C18 N2 C34 C9 -10.8(2) . .
C18 N2 C34 C35 173.36(16) . .
C18 C10 C11 C12 -76.9(2) . .
C18 C10 C11 C16 98.5(2) . .
C19 C18 C20 O3 -133.2(2) . .
C19 C18 C20 N3 49.0(2) . .
C20 N3 C21 C22 171.7(2) . .
C20 N3 C21 C26 -8.7(3) . .
C21 N3 C20 O3 -6.3(3) . .
C21 N3 C20 C18 171.40(18) . .
C21 C22 C23 C24 0.5(4) . .
C22 C21 C26 C25 -0.3(3) . .
C22 C23 C24 C25 -0.3(4) . .
C23 C24 C25 Cl2 -179.3(2) . .
C23 C24 C25 C26 -0.2(4) . .
C24 C25 C26 C21 0.5(4) . .
C26 C21 C22 C23 -0.2(3) . .
C27 N2 C18 C10 -179.61(15) . .
C27 N2 C18 C19 63.0(2) . .
C27 N2 C18 C20 -62.0(2) . .
C27 N2 C34 C9 -166.47(17) . .
C27 N2 C34 C35 17.7(3) . .
C27 C28 C29 C30 174.8(2) . .
C27 C28 C33 C32 -175.4(2) . .
C28 C29 C30 C31 0.2(4) . .
C29 C28 C33 C32 -0.3(3) . .
C29 C30 C31 C32 0.6(4) . .
C30 C31 C32 C33 -1.3(4) . .
C31 C32 C33 C28 1.1(4) . .
C33 C28 C29 C30 -0.4(3) . .
C34 N2 C18 C10 22.83(19) . .
C34 N2 C18 C19 -94.61(18) . .
C34 N2 C18 C20 140.47(16) . .
C34 N2 C27 C28 -64.9(2) . .
C34 C9 C10 C11 -102.47(19) . .
C34 C9 C10 C18 20.10(19) . .
C34 C35 C36 C37 -176.61(18) . .
C34 C35 C40 C39 176.74(18) . .
C35 C36 C37 C38 0.0(3) . .
C36 C35 C40 C39 -1.0(3) . .
C36 C37 C38 C39 -1.0(3) . .
C36 C37 C38 C41 178.7(2) . .
C37 C38 C39 C40 1.0(3) . .
C38 C39 C40 C35 0.0(3) . .
C40 C35 C36 C37 1.0(3) . .
C41 C38 C39 C40 -178.7(2) . .
O4 C42 C43 C44 -15.7(4) . .
C42 O4 C45 C44 15.7(5) . .
C42 C43 C44 C45 24.8(5) . .
C43 C44 C45 O4 -25.4(6) . .
C45 O4 C42 C43 0.3(4) . .
C46 C47 C48 C46 -54.8(5) . 2_755
C48 C46 C47 C48 55.5(5) 2_755 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139204713
