#------------------------------------------------------------------------------
#$Date: 2025-08-21 22:04:39 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301851 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/06/7050612.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_7050612
loop_
_publ_author_name
'Nabih, Khadija'
'Baouid, Abdesselam'
'Hasnaoui, Aissa'
'Selkti, Mohamed'
'Compain, Philippe'
_publ_section_title
;
 1,3-Dipolar cycloaddition of nitrilimines to
 2,4-disubstituted-3H-1,5-benzodiazepines: remarkable effect of
 C4-substituent on diastereoselectivity
;
_journal_issue                   11
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1644
_journal_paper_doi               10.1039/b303995c
_journal_volume                  27
_journal_year                    2003
_chemical_formula_moiety         'C31 H30 Cl2 N6 O4'
_chemical_formula_sum            'C31 H30 Cl2 N6 O4'
_chemical_formula_weight         621.51
_chemical_melting_point          180.5(5)
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 116.76(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.749(3)
_cell_length_b                   23.587(5)
_cell_length_c                   17.758(4)
_cell_measurement_temperature    293(2)
_cell_volume                     6264(3)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'KappaCCD (Nonius, 1998)'
_computing_data_reduction        'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Ortep (Johnson, 1976)'
_computing_publication_material  'WinGX - Version 1.63.02 (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.390
_diffrn_measured_fraction_theta_max 0.390
_diffrn_measurement_device_type  'KappaCCD (Nonius, 1998)'
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0723
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            4102
_diffrn_reflns_theta_full        24.58
_diffrn_reflns_theta_max         24.58
_diffrn_reflns_theta_min         2.57
_exptl_absorpt_coefficient_mu    0.253
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_meas      1.32
_exptl_crystal_density_method    flotation
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             2592
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.673
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     775
_refine_ls_number_reflns         4102
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0612
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0933P)²+13.6892P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1546
_refine_ls_wR_factor_ref         0.1549
_reflns_number_gt                4097
_reflns_number_total             4102
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b303995c.txt
_cod_data_source_block           compound3b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '180-181' was changed to '180.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 
;
_cod_original_cell_volume        6264(2)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7050612
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, 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
Cl1 Cl 0.07513(15) 0.64964(10) 0.17837(13) 0.0346(6) Uani 1 1 d . . .
Cl2 Cl 0.19325(19) 1.02095(11) 0.07058(15) 0.0530(8) Uani 1 1 d . . .
C1 C 0.2408(6) 1.0025(4) 0.1778(5) 0.033(2) Uani 1 1 d . . .
C2 C 0.2967(6) 0.9564(4) 0.2054(5) 0.033(2) Uani 1 1 d . . .
H2 H 0.3089 0.9351 0.1677 0.039 Uiso 1 1 calc R . .
C3 C 0.2224(6) 1.0354(4) 0.2319(6) 0.038(2) Uani 1 1 d . . .
H3 H 0.1833 1.0659 0.2116 0.046 Uiso 1 1 calc R . .
C4 C 0.3347(6) 0.9418(4) 0.2896(5) 0.029(2) Uani 1 1 d . . .
H4 H 0.3706 0.9098 0.3086 0.034 Uiso 1 1 calc R . .
C5 C 0.2629(6) 1.0224(4) 0.3172(6) 0.032(2) Uani 1 1 d . . .
H5 H 0.2526 1.0452 0.3546 0.039 Uiso 1 1 calc R . .
C6 C 0.3187(5) 0.9757(3) 0.3470(5) 0.025(2) Uani 1 1 d . . .
N7 N 0.3590(5) 0.9642(3) 0.4341(4) 0.0275(18) Uani 1 1 d . . .
N8 N 0.3192(5) 0.9890(3) 0.4807(5) 0.0274(17) Uani 1 1 d . . .
C9 C 0.3581(6) 0.9664(4) 0.5546(6) 0.027(2) Uani 1 1 d . . .
C10 C 0.3261(6) 0.9764(5) 0.6195(6) 0.037(2) Uani 1 1 d . . .
O11 O 0.3302(4) 0.9412(3) 0.6702(4) 0.0458(18) Uani 1 1 d . . .
O12 O 0.2911(4) 1.0279(3) 0.6119(4) 0.0479(18) Uani 1 1 d . B .
C13 C 0.2458(9) 1.0380(5) 0.6640(8) 0.079(4) Uani 1 1 d . . .
H13A H 0.1873 1.0203 0.6373 0.095 Uiso 1 1 calc R A 1
H13B H 0.2795 1.0197 0.7181 0.095 Uiso 1 1 calc R A 1
C14A C 0.235(2) 1.0951(8) 0.6778(19) 0.036(8) Uiso 0.51(5) 1 d P B 1
H14A H 0.2049 1.0981 0.7126 0.053 Uiso 0.51(5) 1 calc PR B 1
H14B H 0.2002 1.1135 0.6248 0.053 Uiso 0.51(5) 1 calc PR B 1
H14C H 0.2927 1.1129 0.7057 0.053 Uiso 0.51(5) 1 calc PR B 1
C14B C 0.283(3) 1.0862(12) 0.714(3) 0.068(10) Uiso 0.49(5) 1 d P B 2
H14D H 0.2533 1.0931 0.7489 0.102 Uiso 0.49(5) 1 calc PR B 2
H14E H 0.2754 1.1185 0.6789 0.102 Uiso 0.49(5) 1 calc PR B 2
H14F H 0.3455 1.0800 0.7498 0.102 Uiso 0.49(5) 1 calc PR B 2
N15 N 0.4218(4) 0.9263(3) 0.5635(4) 0.0241(17) Uani 1 1 d . . .
C16 C 0.4141(6) 0.9139(4) 0.4777(5) 0.026(2) Uani 1 1 d . . .
C17 C 0.5053(5) 0.9152(3) 0.4791(5) 0.026(2) Uani 1 1 d . . .
H17A H 0.5385 0.8821 0.5077 0.039 Uiso 1 1 calc R . .
H17B H 0.5370 0.9485 0.5083 0.039 Uiso 1 1 calc R . .
H17C H 0.4981 0.9157 0.4224 0.039 Uiso 1 1 calc R . .
C18 C 0.3628(6) 0.8576(3) 0.4423(5) 0.029(2) Uani 1 1 d . . .
H18A H 0.3817 0.8419 0.4024 0.035 Uiso 1 1 calc R . .
H18B H 0.2994 0.8660 0.4117 0.035 Uiso 1 1 calc R . .
C19 C 0.3768(5) 0.8121(3) 0.5105(5) 0.022(2) Uani 1 1 d . . .
C20 C 0.3174(5) 0.8190(4) 0.5538(5) 0.030(2) Uani 1 1 d . . .
H20A H 0.2559 0.8192 0.5123 0.045 Uiso 1 1 calc R . .
H20B H 0.3312 0.8542 0.5844 0.045 Uiso 1 1 calc R . .
H20C H 0.3275 0.7881 0.5923 0.045 Uiso 1 1 calc R . .
N21 N 0.4725(4) 0.8109(3) 0.5726(4) 0.0231(17) Uani 1 1 d . . .
C22 C 0.5098(5) 0.8458(4) 0.6460(5) 0.028(2) Uani 1 1 d . . .
C23 C 0.5694(6) 0.8242(4) 0.7237(5) 0.033(2) Uani 1 1 d . . .
H23 H 0.5863 0.7864 0.7282 0.039 Uiso 1 1 calc R . .
C24 C 0.6040(6) 0.8583(4) 0.7944(6) 0.038(2) Uani 1 1 d . . .
H24 H 0.6415 0.8428 0.8467 0.046 Uiso 1 1 calc R . .
C25 C 0.5839(6) 0.9134(5) 0.7881(6) 0.039(3) Uani 1 1 d . . .
H25 H 0.6093 0.9364 0.8356 0.047 Uiso 1 1 calc R . .
C26 C 0.5263(6) 0.9363(4) 0.7119(5) 0.034(2) Uani 1 1 d . . .
H26 H 0.5137 0.9749 0.7083 0.041 Uiso 1 1 calc R . .
C27 C 0.4864(5) 0.9029(4) 0.6404(5) 0.025(2) Uani 1 1 d . . .
C28 C 0.5114(5) 0.7645(3) 0.5554(5) 0.022(2) Uani 1 1 d . . .
C29 C 0.6092(6) 0.7593(4) 0.5869(5) 0.029(2) Uani 1 1 d . . .
O30 O 0.6606(4) 0.7994(2) 0.6076(4) 0.0322(15) Uani 1 1 d . . .
O31 O 0.6334(4) 0.7051(3) 0.5875(4) 0.0431(17) Uani 1 1 d . . .
C32 C 0.7268(6) 0.6950(4) 0.6078(8) 0.059(3) Uani 1 1 d . . .
H32A H 0.7629 0.6944 0.6685 0.070 Uiso 1 1 calc R . .
H32B H 0.7485 0.7252 0.5849 0.070 Uiso 1 1 calc R . .
C33 C 0.7346(7) 0.6408(5) 0.5721(8) 0.080(4) Uani 1 1 d . . .
H33A H 0.7962 0.6339 0.5860 0.120 Uiso 1 1 calc R . .
H33B H 0.6999 0.6419 0.5119 0.120 Uiso 1 1 calc R . .
H33C H 0.7129 0.6111 0.5948 0.120 Uiso 1 1 calc R . .
N34 N 0.4571(4) 0.7314(3) 0.4988(4) 0.0260(17) Uani 1 1 d . . .
N35 N 0.3732(5) 0.7538(3) 0.4773(4) 0.0252(17) Uani 1 1 d . . .
C36 C 0.3006(6) 0.7306(3) 0.4062(5) 0.024(2) Uani 1 1 d . . .
C37 C 0.3153(6) 0.6813(4) 0.3691(5) 0.031(2) Uani 1 1 d . . .
H37 H 0.3719 0.6650 0.3925 0.037 Uiso 1 1 calc R . .
C38 C 0.2157(5) 0.7540(3) 0.3709(5) 0.023(2) Uani 1 1 d . . .
H38 H 0.2050 0.7866 0.3944 0.028 Uiso 1 1 calc R . .
C39 C 0.2474(6) 0.6566(4) 0.2990(5) 0.032(2) Uani 1 1 d . . .
H39 H 0.2583 0.6247 0.2743 0.038 Uiso 1 1 calc R . .
C40 C 0.1462(6) 0.7293(4) 0.3010(5) 0.027(2) Uani 1 1 d . . .
H40 H 0.0894 0.7453 0.2776 0.032 Uiso 1 1 calc R . .
C41 C 0.1627(6) 0.6803(3) 0.2661(5) 0.027(2) Uani 1 1 d . . .
Cl3 Cl 0.10732(17) 0.92978(11) 0.51021(14) 0.0464(7) Uani 1 1 d . . .
Cl4 Cl 0.58758(15) 0.79428(11) 0.36447(15) 0.0463(7) Uani 1 1 d . . .
C101 C 0.0749(6) 0.9012(4) 0.4092(5) 0.026(2) Uani 1 1 d . . .
C102 C 0.1143(6) 0.9213(4) 0.3620(5) 0.030(2) Uani 1 1 d . . .
H102 H 0.1577 0.9495 0.3828 0.037 Uiso 1 1 calc R . .
C103 C 0.0103(5) 0.8598(3) 0.3798(5) 0.024(2) Uani 1 1 d . . .
H103 H -0.0152 0.8465 0.4133 0.029 Uiso 1 1 calc R . .
C104 C 0.0881(6) 0.8984(4) 0.2811(5) 0.027(2) Uani 1 1 d . . .
H104 H 0.1152 0.9109 0.2486 0.032 Uiso 1 1 calc R . .
C105 C -0.0159(5) 0.8386(3) 0.3003(5) 0.022(2) Uani 1 1 d . . .
H105 H -0.0601 0.8109 0.2798 0.027 Uiso 1 1 calc R . .
C106 C 0.0220(5) 0.8573(3) 0.2496(5) 0.0190(19) Uani 1 1 d . . .
N107 N -0.0085(4) 0.8349(3) 0.1677(4) 0.0226(16) Uani 1 1 d . . .
N108 N -0.0549(4) 0.7835(3) 0.1515(4) 0.0206(16) Uani 1 1 d . . .
C109 C -0.0726(5) 0.7705(3) 0.0743(5) 0.021(2) Uani 1 1 d . . .
C110 C -0.1119(5) 0.7160(3) 0.0362(5) 0.021(2) Uani 1 1 d . . .
O111 O -0.1015(4) 0.6935(2) -0.0201(3) 0.0278(14) Uani 1 1 d . . .
O112 O -0.1612(4) 0.6938(2) 0.0709(3) 0.0271(14) Uani 1 1 d . . .
C113 C -0.2021(6) 0.6386(3) 0.0394(5) 0.030(2) Uani 1 1 d . . .
H11A H -0.2278 0.6384 -0.0217 0.036 Uiso 1 1 calc R . .
H11B H -0.2503 0.6326 0.0547 0.036 Uiso 1 1 calc R . .
C114 C -0.1355(6) 0.5905(4) 0.0743(6) 0.035(2) Uani 1 1 d . . .
H11C H -0.1650 0.5552 0.0517 0.052 Uiso 1 1 calc R . .
H11D H -0.1112 0.5899 0.1347 0.052 Uiso 1 1 calc R . .
H11E H -0.0881 0.5961 0.0588 0.052 Uiso 1 1 calc R . .
N115 N -0.0386(4) 0.8091(3) 0.0370(4) 0.0208(16) Uani 1 1 d . . .
C116 C 0.0209(5) 0.8494(4) 0.1019(5) 0.024(2) Uani 1 1 d . . .
C117 C 0.0004(6) 0.9101(3) 0.0735(5) 0.028(2) Uani 1 1 d . . .
H11F H 0.0408 0.9347 0.1171 0.043 Uiso 1 1 calc R . .
H11G H -0.0600 0.9188 0.0622 0.043 Uiso 1 1 calc R . .
H11H H 0.0073 0.9155 0.0232 0.043 Uiso 1 1 calc R . .
C118 C 0.1211(5) 0.8324(4) 0.1315(5) 0.024(2) Uani 1 1 d . . .
H11I H 0.1585 0.8652 0.1567 0.029 Uiso 1 1 calc R . .
H11J H 0.1373 0.8035 0.1748 0.029 Uiso 1 1 calc R . .
C119 C 0.1406(5) 0.8098(3) 0.0602(5) 0.020(2) Uani 1 1 d . . .
C120 C 0.1268(6) 0.7466(3) 0.0458(5) 0.027(2) Uani 1 1 d . . .
H12A H 0.0682 0.7366 0.0385 0.041 Uiso 1 1 calc R . .
H12B H 0.1710 0.7267 0.0937 0.041 Uiso 1 1 calc R . .
H12C H 0.1326 0.7363 -0.0038 0.041 Uiso 1 1 calc R . .
N121 N 0.0868(4) 0.8415(3) -0.0195(4) 0.0215(16) Uani 1 1 d . . .
C122 C -0.0005(5) 0.8282(3) -0.0777(5) 0.021(2) Uani 1 1 d . . .
C123 C -0.0279(6) 0.8293(3) -0.1639(5) 0.023(2) Uani 1 1 d . . .
H123 H 0.0136 0.8376 -0.1837 0.028 Uiso 1 1 calc R . .
C124 C -0.1160(6) 0.8184(3) -0.2213(5) 0.031(2) Uani 1 1 d . . .
H124 H -0.1325 0.8194 -0.2788 0.037 Uiso 1 1 calc R . .
C125 C -0.1786(6) 0.8062(4) -0.1943(5) 0.030(2) Uani 1 1 d . . .
H125 H -0.2377 0.7992 -0.2330 0.036 Uiso 1 1 calc R . .
C126 C -0.1526(6) 0.8043(3) -0.1079(5) 0.029(2) Uani 1 1 d . . .
H126 H -0.1947 0.7961 -0.0887 0.035 Uiso 1 1 calc R . .
C127 C -0.0647(6) 0.8146(3) -0.0505(5) 0.022(2) Uani 1 1 d . . .
C128 C 0.1445(6) 0.8777(3) -0.0333(5) 0.021(2) Uani 1 1 d . . .
C129 C 0.1120(6) 0.9270(3) -0.0900(5) 0.026(2) Uani 1 1 d . . .
O130 O 0.0412(4) 0.9503(2) -0.1080(4) 0.0338(15) Uani 1 1 d . . .
O131 O 0.1727(4) 0.9450(2) -0.1147(4) 0.0381(16) Uani 1 1 d . . .
C132 C 0.1539(7) 1.0007(4) -0.1585(6) 0.045(3) Uani 1 1 d . . .
H13C H 0.2094 1.0170 -0.1530 0.054 Uiso 1 1 calc R . .
H13D H 0.1291 1.0263 -0.1317 0.054 Uiso 1 1 calc R . .
C133 C 0.0902(8) 0.9954(4) -0.2493(6) 0.057(3) Uani 1 1 d . . .
H13E H 0.0798 1.0321 -0.2754 0.086 Uiso 1 1 calc R . .
H13F H 0.0347 0.9800 -0.2550 0.086 Uiso 1 1 calc R . .
H13G H 0.1150 0.9706 -0.2763 0.086 Uiso 1 1 calc R . .
N134 N 0.2277(5) 0.8710(3) 0.0182(4) 0.0264(17) Uani 1 1 d . . .
N135 N 0.2316(4) 0.8268(3) 0.0716(4) 0.0245(17) Uani 1 1 d . . .
C136 C 0.3139(6) 0.8176(3) 0.1410(5) 0.022(2) Uani 1 1 d . . .
C137 C 0.3910(6) 0.8380(3) 0.1390(6) 0.029(2) Uani 1 1 d . . .
H137 H 0.3860 0.8567 0.0910 0.035 Uiso 1 1 calc R . .
C138 C 0.3253(6) 0.7860(4) 0.2113(5) 0.026(2) Uani 1 1 d . . .
H138 H 0.2756 0.7696 0.2129 0.031 Uiso 1 1 calc R . .
C139 C 0.4091(6) 0.7783(3) 0.2792(5) 0.028(2) Uani 1 1 d . . .
H139 H 0.4150 0.7571 0.3256 0.033 Uiso 1 1 calc R . .
C140 C 0.4737(6) 0.8313(4) 0.2058(6) 0.035(2) Uani 1 1 d . . .
H140 H 0.5238 0.8463 0.2032 0.042 Uiso 1 1 calc R . .
C141 C 0.4834(6) 0.8021(4) 0.2775(6) 0.034(2) Uani 1 1 d . . .
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'
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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_publ_flag
C2 C1 C3 121.9(8) . . ?
C2 C1 Cl2 119.2(7) . . ?
C3 C1 Cl2 118.9(7) . . ?
C1 C2 C4 119.4(8) . . ?
C1 C2 H2 120.3 . . ?
C4 C2 H2 120.3 . . ?
C1 C3 C5 119.1(8) . . ?
C1 C3 H3 120.5 . . ?
C5 C3 H3 120.5 . . ?
C2 C4 C6 119.8(8) . . ?
C2 C4 H4 120.1 . . ?
C6 C4 H4 120.1 . . ?
C3 C5 C6 120.5(8) . . ?
C3 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C4 119.2(8) . . ?
C5 C6 N7 118.7(8) . . ?
C4 C6 N7 122.1(8) . . ?
N8 N7 C6 116.6(7) . . ?
N8 N7 C16 111.9(6) . . ?
C6 N7 C16 127.2(7) . . ?
C9 N8 N7 105.8(7) . . ?
N8 C9 N15 114.2(7) . . ?
N8 C9 C10 121.9(8) . . ?
N15 C9 C10 123.3(8) . . ?
O11 C10 O12 125.5(8) . . ?
O11 C10 C9 123.3(9) . . ?
O12 C10 C9 111.2(9) . . ?
C10 O12 C13 114.6(8) . . ?
C14A C13 C14B 33.2(13) . . ?
C14A C13 O12 114.5(11) . . ?
C14B C13 O12 109.2(13) . . ?
C14A C13 H13A 108.6 . . ?
C14B C13 H13A 136.0 . . ?
O12 C13 H13A 108.6 . . ?
C14A C13 H13B 108.6 . . ?
C14B C13 H13B 80.6 . . ?
O12 C13 H13B 108.6 . . ?
H13A C13 H13B 107.6 . . ?
C13 C14A H14A 109.5 . . ?
C13 C14A H14B 109.5 . . ?
H14A C14A H14B 109.5 . . ?
C13 C14A H14C 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
C13 C14B H14D 109.5 . . ?
C13 C14B H14E 109.5 . . ?
H14D C14B H14E 109.5 . . ?
C13 C14B H14F 109.4 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?
C9 N15 C27 126.2(7) . . ?
C9 N15 C16 108.0(6) . . ?
C27 N15 C16 125.7(7) . . ?
N7 C16 N15 97.1(6) . . ?
N7 C16 C17 112.2(7) . . ?
N15 C16 C17 110.7(7) . . ?
N7 C16 C18 111.8(7) . . ?
N15 C16 C18 110.9(7) . . ?
C17 C16 C18 113.1(7) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 C19 114.4(7) . . ?
C16 C18 H18A 108.7 . . ?
C19 C18 H18A 108.7 . . ?
C16 C18 H18B 108.7 . . ?
C19 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
N21 C19 N35 96.5(6) . . ?
N21 C19 C20 111.3(6) . . ?
N35 C19 C20 112.5(6) . . ?
N21 C19 C18 109.0(6) . . ?
N35 C19 C18 111.3(6) . . ?
C20 C19 C18 114.7(7) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C28 N21 C22 127.3(7) . . ?
C28 N21 C19 108.2(6) . . ?
C22 N21 C19 123.4(6) . . ?
C23 C22 C27 118.6(8) . . ?
C23 C22 N21 121.4(8) . . ?
C27 C22 N21 120.0(7) . . ?
C24 C23 C22 120.8(9) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C25 C24 C23 120.2(9) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C24 C25 C26 120.4(9) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C25 C26 C27 121.1(9) . . ?
C25 C26 H26 119.4 . . ?
C27 C26 H26 119.4 . . ?
C26 C27 C22 118.7(8) . . ?
C26 C27 N15 120.5(8) . . ?
C22 C27 N15 120.8(7) . . ?
N34 C28 N21 114.9(7) . . ?
N34 C28 C29 121.6(8) . . ?
N21 C28 C29 122.4(8) . . ?
O30 C29 O31 124.6(8) . . ?
O30 C29 C28 124.2(8) . . ?
O31 C29 C28 111.2(8) . . ?
C29 O31 C32 116.5(7) . . ?
O31 C32 C33 109.4(8) . . ?
O31 C32 H32A 109.8 . . ?
C33 C32 H32A 109.8 . . ?
O31 C32 H32B 109.8 . . ?
C33 C32 H32B 109.8 . . ?
H32A C32 H32B 108.2 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C28 N34 N35 105.1(7) . . ?
N34 N35 C36 117.3(6) . . ?
N34 N35 C19 112.9(6) . . ?
C36 N35 C19 125.3(7) . . ?
C38 C36 N35 123.1(8) . . ?
C38 C36 C37 118.5(8) . . ?
N35 C36 C37 118.4(7) . . ?
C39 C37 C36 121.5(8) . . ?
C39 C37 H37 119.2 . . ?
C36 C37 H37 119.2 . . ?
C36 C38 C40 120.9(8) . . ?
C36 C38 H38 119.6 . . ?
C40 C38 H38 119.6 . . ?
C37 C39 C41 118.8(8) . . ?
C37 C39 H39 120.6 . . ?
C41 C39 H39 120.6 . . ?
C38 C40 C41 119.3(8) . . ?
C38 C40 H40 120.4 . . ?
C41 C40 H40 120.4 . . ?
C39 C41 C40 121.1(8) . . ?
C39 C41 Cl1 119.9(7) . . ?
C40 C41 Cl1 119.0(7) . . ?
C102 C101 C103 122.0(8) . . ?
C102 C101 Cl3 118.7(7) . . ?
C103 C101 Cl3 119.3(6) . . ?
C101 C102 C104 118.5(8) . . ?
C101 C102 H102 120.7 . . ?
C104 C102 H102 120.7 . . ?
C105 C103 C101 118.9(8) . . ?
C105 C103 H103 120.6 . . ?
C101 C103 H103 120.6 . . ?
C106 C104 C102 120.5(8) . . ?
C106 C104 H104 119.7 . . ?
C102 C104 H104 119.7 . . ?
C103 C105 C106 121.6(8) . . ?
C103 C105 H105 119.2 . . ?
C106 C105 H105 119.2 . . ?
C104 C106 C105 118.4(7) . . ?
C104 C106 N107 122.2(7) . . ?
C105 C106 N107 119.4(7) . . ?
N108 N107 C106 116.6(6) . . ?
N108 N107 C116 112.7(6) . . ?
C106 N107 C116 128.7(6) . . ?
C109 N108 N107 105.2(6) . . ?
N108 C109 N115 113.6(7) . . ?
N108 C109 C110 122.3(7) . . ?
N115 C109 C110 123.4(7) . . ?
O111 C110 O112 123.8(8) . . ?
O111 C110 C109 124.4(7) . . ?
O112 C110 C109 111.9(7) . . ?
C110 O112 C113 116.9(6) . . ?
O112 C113 C114 112.2(7) . . ?
O112 C113 H11A 109.2 . . ?
C114 C113 H11A 109.2 . . ?
O112 C113 H11B 109.2 . . ?
C114 C113 H11B 109.2 . . ?
H11A C113 H11B 107.9 . . ?
C113 C114 H11C 109.5 . . ?
C113 C114 H11D 109.5 . . ?
H11C C114 H11D 109.5 . . ?
C113 C114 H11E 109.5 . . ?
H11C C114 H11E 109.5 . . ?
H11D C114 H11E 109.5 . . ?
C109 N115 C127 126.3(7) . . ?
C109 N115 C116 109.1(6) . . ?
C127 N115 C116 124.1(6) . . ?
N115 C116 N107 96.7(6) . . ?
N115 C116 C117 112.2(7) . . ?
N107 C116 C117 111.9(6) . . ?
N115 C116 C118 109.9(6) . . ?
N107 C116 C118 110.9(6) . . ?
C117 C116 C118 113.9(7) . . ?
C116 C117 H11F 109.5 . . ?
C116 C117 H11G 109.5 . . ?
H11F C117 H11G 109.5 . . ?
C116 C117 H11H 109.5 . . ?
H11F C117 H11H 109.5 . . ?
H11G C117 H11H 109.5 . . ?
C119 C118 C116 113.9(6) . . ?
C119 C118 H11I 108.8 . . ?
C116 C118 H11I 108.8 . . ?
C119 C118 H11J 108.8 . . ?
C116 C118 H11J 108.8 . . ?
H11I C118 H11J 107.7 . . ?
N121 C119 N135 97.9(5) . . ?
N121 C119 C120 110.7(6) . . ?
N135 C119 C120 110.8(6) . . ?
N121 C119 C118 110.2(6) . . ?
N135 C119 C118 112.1(6) . . ?
C120 C119 C118 114.0(6) . . ?
C119 C120 H12A 109.5 . . ?
C119 C120 H12B 109.5 . . ?
H12A C120 H12B 109.5 . . ?
C119 C120 H12C 109.5 . . ?
H12A C120 H12C 109.5 . . ?
H12B C120 H12C 109.5 . . ?
C128 N121 C122 125.9(7) . . ?
C128 N121 C119 107.7(6) . . ?
C122 N121 C119 125.1(6) . . ?
C123 C122 N121 122.0(7) . . ?
C123 C122 C127 117.5(7) . . ?
N121 C122 C127 120.5(7) . . ?
C122 C123 C124 121.4(8) . . ?
C122 C123 H123 119.3 . . ?
C124 C123 H123 119.3 . . ?
C125 C124 C123 120.8(8) . . ?
C125 C124 H124 119.6 . . ?
C123 C124 H124 119.6 . . ?
C124 C125 C126 119.0(8) . . ?
C124 C125 H125 120.5 . . ?
C126 C125 H125 120.5 . . ?
C127 C126 C125 120.4(8) . . ?
C127 C126 H126 119.8 . . ?
C125 C126 H126 119.8 . . ?
C126 C127 C122 120.9(7) . . ?
C126 C127 N115 119.4(7) . . ?
C122 C127 N115 119.6(7) . . ?
N134 C128 N121 114.4(7) . . ?
N134 C128 C129 122.2(7) . . ?
N121 C128 C129 122.3(8) . . ?
O130 C129 O131 124.3(8) . . ?
O130 C129 C128 123.7(7) . . ?
O131 C129 C128 111.9(7) . . ?
C129 O131 C132 115.9(7) . . ?
O131 C132 C133 111.9(8) . . ?
O131 C132 H13C 109.2 . . ?
C133 C132 H13C 109.2 . . ?
O131 C132 H13D 109.2 . . ?
C133 C132 H13D 109.2 . . ?
H13C C132 H13D 107.9 . . ?
C132 C133 H13E 109.5 . . ?
C132 C133 H13F 109.5 . . ?
H13E C133 H13F 109.5 . . ?
C132 C133 H13G 109.5 . . ?
H13E C133 H13G 109.5 . . ?
H13F C133 H13G 109.5 . . ?
C128 N134 N135 106.3(6) . . ?
C136 N135 N134 116.4(6) . . ?
C136 N135 C119 128.3(6) . . ?
N134 N135 C119 112.1(6) . . ?
N135 C136 C137 119.0(7) . . ?
N135 C136 C138 123.9(7) . . ?
C137 C136 C138 117.0(8) . . ?
C140 C137 C136 121.8(8) . . ?
C140 C137 H137 119.1 . . ?
C136 C137 H137 119.1 . . ?
C139 C138 C136 121.6(8) . . ?
C139 C138 H138 119.2 . . ?
C136 C138 H138 119.2 . . ?
C141 C139 C138 119.8(8) . . ?
C141 C139 H139 120.1 . . ?
C138 C139 H139 120.1 . . ?
C137 C140 C141 120.4(8) . . ?
C137 C140 H140 119.8 . . ?
C141 C140 H140 119.8 . . ?
C139 C141 C140 119.1(8) . . ?
C139 C141 Cl4 119.4(7) . . ?
C140 C141 Cl4 121.5(7) . . ?
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
Cl1 C41 1.744(8) . ?
Cl2 C1 1.756(9) . ?
C1 C2 1.374(12) . ?
C1 C3 1.375(12) . ?
C2 C4 1.379(11) . ?
C2 H2 0.9300 . ?
C3 C5 1.386(12) . ?
C3 H3 0.9300 . ?
C4 C6 1.412(11) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(11) . ?
C5 H5 0.9300 . ?
C6 N7 1.406(10) . ?
N7 N8 1.404(9) . ?
N7 C16 1.488(10) . ?
N8 C9 1.289(10) . ?
C9 N15 1.381(10) . ?
C9 C10 1.491(12) . ?
C10 O11 1.204(11) . ?
C10 O12 1.329(11) . ?
O12 C13 1.457(11) . ?
C13 C14A 1.39(2) . ?
C13 C14B 1.41(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14A H14A 0.9600 . ?
C14A H14B 0.9600 . ?
C14A H14C 0.9600 . ?
C14B H14D 0.9600 . ?
C14B H14E 0.9600 . ?
C14B H14F 0.9600 . ?
N15 C27 1.417(10) . ?
N15 C16 1.498(9) . ?
C16 C17 1.517(11) . ?
C16 C18 1.553(11) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.556(11) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 N21 1.481(10) . ?
C19 N35 1.488(10) . ?
C19 C20 1.515(11) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
N21 C28 1.376(10) . ?
N21 C22 1.427(10) . ?
C22 C23 1.386(11) . ?
C22 C27 1.394(12) . ?
C23 C24 1.379(12) . ?
C23 H23 0.9300 . ?
C24 C25 1.335(12) . ?
C24 H24 0.9300 . ?
C25 C26 1.369(12) . ?
C25 H25 0.9300 . ?
C26 C27 1.383(11) . ?
C26 H26 0.9300 . ?
C28 N34 1.274(10) . ?
C28 C29 1.478(11) . ?
C29 O30 1.218(10) . ?
C29 O31 1.340(10) . ?
O31 C32 1.459(10) . ?
C32 C33 1.457(14) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
N34 N35 1.383(9) . ?
N35 C36 1.410(10) . ?
C36 C38 1.385(11) . ?
C36 C37 1.411(11) . ?
C37 C39 1.381(11) . ?
C37 H37 0.9300 . ?
C38 C40 1.391(11) . ?
C38 H38 0.9300 . ?
C39 C41 1.386(11) . ?
C39 H39 0.9300 . ?
C40 C41 1.397(11) . ?
C40 H40 0.9300 . ?
Cl3 C101 1.758(8) . ?
Cl4 C141 1.742(9) . ?
C101 C102 1.365(11) . ?
C101 C103 1.373(11) . ?
C102 C104 1.406(11) . ?
C102 H102 0.9300 . ?
C103 C105 1.372(10) . ?
C103 H103 0.9300 . ?
C104 C106 1.385(11) . ?
C104 H104 0.9300 . ?
C105 C106 1.386(10) . ?
C105 H105 0.9300 . ?
C106 N107 1.409(10) . ?
N107 N108 1.398(8) . ?
N107 C116 1.498(9) . ?
N108 C109 1.301(9) . ?
C109 N115 1.389(9) . ?
C109 C110 1.465(11) . ?
C110 O111 1.211(9) . ?
C110 O112 1.340(9) . ?
O112 C113 1.461(9) . ?
C113 C114 1.514(11) . ?
C113 H11A 0.9700 . ?
C113 H11B 0.9700 . ?
C114 H11C 0.9600 . ?
C114 H11D 0.9600 . ?
C114 H11E 0.9600 . ?
N115 C127 1.418(9) . ?
N115 C116 1.480(10) . ?
C116 C117 1.504(11) . ?
C116 C118 1.568(11) . ?
C117 H11F 0.9600 . ?
C117 H11G 0.9600 . ?
C117 H11H 0.9600 . ?
C118 C119 1.539(10) . ?
C118 H11I 0.9700 . ?
C118 H11J 0.9700 . ?
C119 N121 1.491(9) . ?
C119 N135 1.499(10) . ?
C119 C120 1.513(11) . ?
C120 H12A 0.9600 . ?
C120 H12B 0.9600 . ?
C120 H12C 0.9600 . ?
N121 C128 1.392(10) . ?
N121 C122 1.395(10) . ?
C122 C123 1.386(10) . ?
C122 C127 1.400(10) . ?
C123 C124 1.388(11) . ?
C123 H123 0.9300 . ?
C124 C125 1.367(11) . ?
C124 H124 0.9300 . ?
C125 C126 1.395(11) . ?
C125 H125 0.9300 . ?
C126 C127 1.384(11) . ?
C126 H126 0.9300 . ?
C128 N134 1.288(10) . ?
C128 C129 1.471(11) . ?
C129 O130 1.213(9) . ?
C129 O131 1.344(10) . ?
O131 C132 1.487(10) . ?
C132 C133 1.485(13) . ?
C132 H13C 0.9700 . ?
C132 H13D 0.9700 . ?
C133 H13E 0.9600 . ?
C133 H13F 0.9600 . ?
C133 H13G 0.9600 . ?
N134 N135 1.389(9) . ?
N135 C136 1.392(10) . ?
C136 C137 1.392(11) . ?
C136 C138 1.393(11) . ?
C137 C140 1.368(11) . ?
C137 H137 0.9300 . ?
C138 C139 1.391(11) . ?
C138 H138 0.9300 . ?
C139 C141 1.379(11) . ?
C139 H139 0.9300 . ?
C140 C141 1.391(12) . ?
C140 H140 0.9300 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139175184
