#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/11/7201170.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_7201170
loop_
_publ_author_name
'Yin, Zhenming'
'Wang, Wuyan'
'Du, Miao'
'Wang, Xiuguang'
'Guo, Jianhua'
_publ_section_title
;
 Crystal engineering of 5,5′-bisdiazo-dipyrromethane with
 halogen⋯π synthons
;
_journal_issue                   11
_journal_name_full               CrystEngComm
_journal_page_first              2441
_journal_paper_doi               10.1039/b905568a
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C51 H49 Cl7 N12'
_chemical_formula_sum            'C51 H49 Cl7 N12'
_chemical_formula_weight         1078.17
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                96.321(4)
_cell_angle_beta                 103.106(4)
_cell_angle_gamma                108.281(6)
_cell_formula_units_Z            2
_cell_length_a                   12.100(5)
_cell_length_b                   14.317(5)
_cell_length_c                   17.195(6)
_cell_measurement_reflns_used    6232
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.8
_cell_measurement_theta_min      1.5
_cell_volume                     2701.4(17)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalClear
_computing_publication_material  'CrystalStructure 3.7.0'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'Rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_sigmaI/netI    0.0517
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            27828
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.53
_exptl_absorpt_coefficient_mu    0.414
_exptl_absorpt_correction_T_max  0.9217
_exptl_absorpt_correction_T_min  0.9071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1116
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.712
_refine_diff_density_min         -1.525
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     635
_refine_ls_number_reflns         9503
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.1063
_refine_ls_R_factor_gt           0.0876
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1627P)²+5.6889P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2593
_refine_ls_wR_factor_ref         0.2788
_reflns_number_gt                7407
_reflns_number_total             9503
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b905568a.txt
_cod_data_source_block           shelxl
_cod_database_code               7201170
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.31386(13) 1.61569(9) 0.46009(9) 0.0468(4) Uani 1 1 d . . .
Cl2 Cl -0.39369(12) 0.51677(12) 0.33091(9) 0.0526(4) Uani 1 1 d . . .
Cl3 Cl 1.02142(10) 0.39361(9) 0.36631(9) 0.0426(4) Uani 1 1 d . . .
Cl4 Cl 0.08235(17) -0.49808(10) -0.16112(9) 0.0575(5) Uani 1 1 d . . .
N1 N 0.3610(3) 1.0920(2) 0.1940(2) 0.0189(7) Uani 1 1 d . . .
H1' H 0.3964 1.1051 0.2467 0.023 Uiso 1 1 calc R . .
N2 N 0.2866(3) 1.2322(3) 0.1895(2) 0.0248(8) Uani 1 1 d . . .
N3 N 0.3202(3) 1.2485(3) 0.2681(2) 0.0216(8) Uani 1 1 d . . .
N4 N 0.2752(3) 0.8544(2) 0.2345(2) 0.0196(7) Uani 1 1 d . . .
H4' H 0.2115 0.8520 0.1963 0.023 Uiso 1 1 calc R . .
N5 N 0.1691(3) 0.7590(3) 0.3229(2) 0.0248(8) Uani 1 1 d . . .
N6 N 0.0696(3) 0.7633(3) 0.2792(2) 0.0220(8) Uani 1 1 d . . .
N7 N 0.2848(3) 0.0889(2) 0.36951(19) 0.0158(7) Uani 1 1 d . . .
H7' H 0.2898 0.1250 0.3314 0.019 Uiso 1 1 calc R . .
N8 N 0.5017(3) 0.1220(3) 0.4258(2) 0.0198(7) Uani 1 1 d . . .
N9 N 0.5183(3) 0.1648(2) 0.3650(2) 0.0197(7) Uani 1 1 d . . .
N10 N 0.0416(3) -0.0580(2) 0.21119(19) 0.0181(7) Uani 1 1 d . . .
H10' H 0.0662 -0.1031 0.2334 0.022 Uiso 1 1 calc R . .
N11 N 0.0025(3) -0.1317(3) 0.0666(2) 0.0240(8) Uani 1 1 d . . .
N12 N 0.0530(3) -0.1942(3) 0.0907(2) 0.0231(8) Uani 1 1 d . . .
C1 C 0.3556(4) 1.3567(3) 0.3933(3) 0.0247(9) Uani 1 1 d . . .
H1 H 0.3821 1.3092 0.4193 0.030 Uiso 1 1 calc R . .
C2 C 0.3549(4) 1.4408(3) 0.4398(3) 0.0277(10) Uani 1 1 d . . .
H2 H 0.3798 1.4515 0.4976 0.033 Uiso 1 1 calc R . .
C3 C 0.3170(4) 1.5103(3) 0.4007(3) 0.0316(11) Uani 1 1 d . . .
C4 C 0.2806(4) 1.4963(3) 0.3161(3) 0.0321(10) Uani 1 1 d . . .
H4 H 0.2561 1.5448 0.2904 0.038 Uiso 1 1 calc R . .
C5 C 0.2807(4) 1.4104(3) 0.2699(3) 0.0275(10) Uani 1 1 d . . .
H5 H 0.2556 1.3997 0.2121 0.033 Uiso 1 1 calc R . .
C6 C 0.3178(4) 1.3397(3) 0.3083(3) 0.0216(9) Uani 1 1 d . . .
C7 C 0.2999(4) 1.1478(3) 0.1538(2) 0.0222(9) Uani 1 1 d . . .
C8 C 0.2562(4) 1.1021(4) 0.0714(3) 0.0305(10) Uani 1 1 d . . .
H8 H 0.2118 1.1243 0.0290 0.037 Uiso 1 1 calc R . .
C9 C 0.2902(4) 1.0172(3) 0.0631(2) 0.0265(10) Uani 1 1 d . . .
H9 H 0.2705 0.9702 0.0141 0.032 Uiso 1 1 calc R . .
C10 C 0.3582(4) 1.0138(3) 0.1398(2) 0.0195(8) Uani 1 1 d . . .
C11 C 0.4288(4) 0.9461(3) 0.1647(2) 0.0215(9) Uani 1 1 d . . .
C12 C 0.5664(4) 1.0092(4) 0.1926(3) 0.0272(10) Uani 1 1 d . . .
H12A H 0.5833 1.0581 0.2430 0.033 Uiso 1 1 calc R . .
H12B H 0.6121 0.9639 0.2060 0.033 Uiso 1 1 calc R . .
C13 C 0.6128(5) 1.0656(5) 0.1303(3) 0.0435(13) Uani 1 1 d . . .
H13A H 0.6018 1.0177 0.0814 0.065 Uiso 1 1 calc R . .
H13B H 0.6990 1.1055 0.1533 0.065 Uiso 1 1 calc R . .
H13C H 0.5675 1.1102 0.1160 0.065 Uiso 1 1 calc R . .
C14 C 0.3986(4) 0.8592(4) 0.0912(3) 0.0305(10) Uani 1 1 d . . .
H14A H 0.3096 0.8250 0.0721 0.037 Uiso 1 1 calc R . .
H14B H 0.4248 0.8887 0.0461 0.037 Uiso 1 1 calc R . .
C15 C 0.4569(6) 0.7810(4) 0.1091(4) 0.0548(17) Uani 1 1 d . . .
H15A H 0.5453 0.8129 0.1245 0.082 Uiso 1 1 calc R . .
H15B H 0.4308 0.7283 0.0604 0.082 Uiso 1 1 calc R . .
H15C H 0.4323 0.7514 0.1539 0.082 Uiso 1 1 calc R . .
C16 C 0.3936(4) 0.9011(3) 0.2359(2) 0.0210(9) Uani 1 1 d . . .
C17 C 0.4668(4) 0.8889(3) 0.3072(3) 0.0273(10) Uani 1 1 d . . .
H17 H 0.5528 0.9146 0.3245 0.033 Uiso 1 1 calc R . .
C18 C 0.3910(4) 0.8323(4) 0.3482(3) 0.0313(10) Uani 1 1 d . . .
H18 H 0.4162 0.8119 0.3979 0.038 Uiso 1 1 calc R . .
C19 C 0.2719(4) 0.8110(3) 0.3032(3) 0.0242(9) Uani 1 1 d . . .
C20 C -0.0367(4) 0.7034(3) 0.2960(2) 0.0226(9) Uani 1 1 d . . .
C21 C -0.0386(4) 0.6407(3) 0.3535(3) 0.0265(10) Uani 1 1 d . . .
H21 H 0.0351 0.6370 0.3846 0.032 Uiso 1 1 calc R . .
C22 C -0.1472(4) 0.5845(3) 0.3647(3) 0.0319(11) Uani 1 1 d . . .
H22 H -0.1487 0.5421 0.4036 0.038 Uiso 1 1 calc R . .
C23 C -0.2556(4) 0.5901(4) 0.3185(3) 0.0347(11) Uani 1 1 d . . .
C24 C -0.2555(4) 0.6507(4) 0.2608(3) 0.0380(12) Uani 1 1 d . . .
H24 H -0.3295 0.6533 0.2292 0.046 Uiso 1 1 calc R . .
C25 C -0.1463(4) 0.7073(3) 0.2499(3) 0.0306(10) Uani 1 1 d . . .
H25 H -0.1455 0.7492 0.2107 0.037 Uiso 1 1 calc R . .
C26 C 0.7401(4) 0.2181(3) 0.4310(3) 0.0219(9) Uani 1 1 d . . .
H26 H 0.7278 0.1826 0.4736 0.026 Uiso 1 1 calc R . .
C27 C 0.8571(4) 0.2728(3) 0.4291(3) 0.0266(10) Uani 1 1 d . . .
H27 H 0.9249 0.2742 0.4705 0.032 Uiso 1 1 calc R . .
C28 C 0.8748(4) 0.3249(3) 0.3674(3) 0.0276(10) Uani 1 1 d . . .
C29 C 0.7774(4) 0.3239(3) 0.3058(3) 0.0327(11) Uani 1 1 d . . .
H29 H 0.7904 0.3597 0.2634 0.039 Uiso 1 1 calc R . .
C30 C 0.6607(4) 0.2698(3) 0.3073(3) 0.0277(10) Uani 1 1 d . . .
H30 H 0.5933 0.2690 0.2658 0.033 Uiso 1 1 calc R . .
C31 C 0.6416(4) 0.2166(3) 0.3693(2) 0.0205(9) Uani 1 1 d . . .
C32 C 0.3825(4) 0.0777(3) 0.4229(2) 0.0189(8) Uani 1 1 d . . .
C33 C 0.3368(4) 0.0139(3) 0.4729(3) 0.0238(9) Uani 1 1 d . . .
H33 H 0.3828 -0.0069 0.5156 0.029 Uiso 1 1 calc R . .
C34 C 0.2103(4) -0.0136(3) 0.4484(2) 0.0216(9) Uani 1 1 d . . .
H34 H 0.1548 -0.0578 0.4708 0.026 Uiso 1 1 calc R . .
C35 C 0.1802(3) 0.0353(3) 0.3851(2) 0.0166(8) Uani 1 1 d . . .
C36 C 0.0601(3) 0.0453(3) 0.3448(2) 0.0165(8) Uani 1 1 d . . .
C37 C 0.0700(4) 0.1554(3) 0.3748(2) 0.0189(8) Uani 1 1 d . . .
H37A H 0.1258 0.2005 0.3495 0.023 Uiso 1 1 calc R . .
H37B H -0.0107 0.1610 0.3549 0.023 Uiso 1 1 calc R . .
C38 C 0.1147(4) 0.1924(3) 0.4668(3) 0.0266(9) Uani 1 1 d . . .
H38A H 0.0580 0.1508 0.4925 0.040 Uiso 1 1 calc R . .
H38B H 0.1198 0.2623 0.4797 0.040 Uiso 1 1 calc R . .
H38C H 0.1950 0.1880 0.4874 0.040 Uiso 1 1 calc R . .
C39 C -0.0424(3) -0.0310(3) 0.3699(2) 0.0213(9) Uani 1 1 d . . .
H39A H -0.0372 -0.0984 0.3578 0.026 Uiso 1 1 calc R . .
H39B H -0.0282 -0.0130 0.4295 0.026 Uiso 1 1 calc R . .
C40 C -0.1708(4) -0.0365(4) 0.3277(3) 0.0311(10) Uani 1 1 d . . .
H40A H -0.1790 0.0287 0.3421 0.047 Uiso 1 1 calc R . .
H40B H -0.2296 -0.0879 0.3454 0.047 Uiso 1 1 calc R . .
H40C H -0.1860 -0.0538 0.2686 0.047 Uiso 1 1 calc R . .
C41 C 0.0346(3) 0.0255(3) 0.2530(2) 0.0165(8) Uani 1 1 d . . .
C42 C -0.0061(4) 0.0778(3) 0.1961(2) 0.0244(9) Uani 1 1 d . . .
H42 H -0.0178 0.1399 0.2082 0.029 Uiso 1 1 calc R . .
C43 C -0.0271(4) 0.0240(3) 0.1183(3) 0.0272(10) Uani 1 1 d . . .
H43 H -0.0567 0.0419 0.0682 0.033 Uiso 1 1 calc R . .
C44 C 0.0035(4) -0.0610(3) 0.1275(2) 0.0223(9) Uani 1 1 d . . .
C45 C 0.0514(4) -0.2673(3) 0.0262(3) 0.0248(9) Uani 1 1 d . . .
C46 C 0.0036(4) -0.2719(4) -0.0571(3) 0.0312(10) Uani 1 1 d . . .
H46 H -0.0359 -0.2267 -0.0740 0.037 Uiso 1 1 calc R . .
C47 C 0.0136(5) -0.3418(4) -0.1149(3) 0.0356(11) Uani 1 1 d . . .
H47 H -0.0176 -0.3442 -0.1713 0.043 Uiso 1 1 calc R . .
C48 C 0.0701(5) -0.4086(4) -0.0891(3) 0.0381(12) Uani 1 1 d . . .
C49 C 0.1152(5) -0.4067(4) -0.0065(3) 0.0407(12) Uani 1 1 d . . .
H49 H 0.1521 -0.4534 0.0103 0.049 Uiso 1 1 calc R . .
C50 C 0.1054(4) -0.3362(3) 0.0503(3) 0.0308(10) Uani 1 1 d . . .
H50 H 0.1359 -0.3345 0.1067 0.037 Uiso 1 1 calc R . .
C51 C 0.3912(10) 0.3914(7) 0.0750(6) 0.097(3) Uani 1 1 d . . .
H51 H 0.3461 0.3490 0.1081 0.116 Uiso 1 1 calc R . .
Cl5 Cl 0.3957(3) 0.51393(19) 0.10320(17) 0.1062(8) Uani 1 1 d . . .
Cl6 Cl 0.3123(3) 0.3420(2) -0.02826(17) 0.1246(10) Uani 1 1 d . . .
Cl7 Cl 0.5378(3) 0.3858(2) 0.09695(17) 0.1166(9) 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'
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
C10 N1 C7 109.8(3) . . ?
C10 N1 H1' 125.1 . . ?
C7 N1 H1' 125.1 . . ?
N3 N2 C7 113.5(3) . . ?
N2 N3 C6 115.7(3) . . ?
C16 N4 C19 109.0(3) . . ?
C16 N4 H4' 125.5 . . ?
C19 N4 H4' 125.5 . . ?
N6 N5 C19 115.3(3) . . ?
N5 N6 C20 114.8(3) . . ?
C35 N7 C32 109.5(3) . . ?
C35 N7 H7' 125.2 . . ?
C32 N7 H7' 125.2 . . ?
N9 N8 C32 114.0(3) . . ?
N8 N9 C31 114.8(3) . . ?
C41 N10 C44 109.4(3) . . ?
C41 N10 H10' 125.3 . . ?
C44 N10 H10' 125.3 . . ?
N12 N11 C44 115.0(3) . . ?
N11 N12 C45 114.2(3) . . ?
C2 C1 C6 121.1(4) . . ?
C2 C1 H1 119.5 . . ?
C6 C1 H1 119.5 . . ?
C1 C2 C3 118.8(4) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 121.5(4) . . ?
C4 C3 Cl1 120.0(4) . . ?
C2 C3 Cl1 118.5(4) . . ?
C5 C4 C3 119.1(4) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 120.1(4) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 119.5(4) . . ?
C1 C6 N3 115.0(4) . . ?
C5 C6 N3 125.5(4) . . ?
N2 C7 N1 125.3(4) . . ?
N2 C7 C8 127.2(4) . . ?
N1 C7 C8 107.4(4) . . ?
C7 C8 C9 107.2(4) . . ?
C7 C8 H8 126.4 . . ?
C9 C8 H8 126.4 . . ?
C10 C9 C8 108.0(4) . . ?
C10 C9 H9 126.0 . . ?
C8 C9 H9 126.0 . . ?
N1 C10 C9 107.5(4) . . ?
N1 C10 C11 121.6(3) . . ?
C9 C10 C11 130.7(4) . . ?
C10 C11 C16 110.1(3) . . ?
C10 C11 C12 109.1(3) . . ?
C16 C11 C12 108.5(3) . . ?
C10 C11 C14 109.1(3) . . ?
C16 C11 C14 108.9(3) . . ?
C12 C11 C14 111.1(3) . . ?
C13 C12 C11 114.6(4) . . ?
C13 C12 H12A 108.6 . . ?
C11 C12 H12A 108.6 . . ?
C13 C12 H12B 108.6 . . ?
C11 C12 H12B 108.6 . . ?
H12A C12 H12B 107.6 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C11 115.0(4) . . ?
C15 C14 H14A 108.5 . . ?
C11 C14 H14A 108.5 . . ?
C15 C14 H14B 108.5 . . ?
C11 C14 H14B 108.5 . . ?
H14A C14 H14B 107.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N4 C16 C17 107.6(4) . . ?
N4 C16 C11 122.2(3) . . ?
C17 C16 C11 129.9(4) . . ?
C18 C17 C16 108.0(4) . . ?
C18 C17 H17 126.0 . . ?
C16 C17 H17 126.0 . . ?
C19 C18 C17 107.8(4) . . ?
C19 C18 H18 126.1 . . ?
C17 C18 H18 126.1 . . ?
N5 C19 C18 126.8(4) . . ?
N5 C19 N4 125.7(4) . . ?
C18 C19 N4 107.5(4) . . ?
C25 C20 C21 119.4(4) . . ?
C25 C20 N6 116.1(4) . . ?
C21 C20 N6 124.5(4) . . ?
C22 C21 C20 120.0(4) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C23 119.7(4) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C24 C23 C22 121.0(4) . . ?
C24 C23 Cl2 119.1(4) . . ?
C22 C23 Cl2 119.8(4) . . ?
C25 C24 C23 119.1(5) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C24 C25 C20 120.7(4) . . ?
C24 C25 H25 119.6 . . ?
C20 C25 H25 119.6 . . ?
C27 C26 C31 118.9(4) . . ?
C27 C26 H26 120.5 . . ?
C31 C26 H26 120.5 . . ?
C28 C27 C26 120.4(4) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C27 C28 C29 121.1(4) . . ?
C27 C28 Cl3 119.8(4) . . ?
C29 C28 Cl3 119.1(4) . . ?
C30 C29 C28 118.9(4) . . ?
C30 C29 H29 120.5 . . ?
C28 C29 H29 120.5 . . ?
C29 C30 C31 120.6(4) . . ?
C29 C30 H30 119.7 . . ?
C31 C30 H30 119.7 . . ?
C30 C31 C26 120.1(4) . . ?
C30 C31 N9 115.5(4) . . ?
C26 C31 N9 124.4(4) . . ?
N8 C32 N7 125.7(4) . . ?
N8 C32 C33 126.7(4) . . ?
N7 C32 C33 107.6(3) . . ?
C32 C33 C34 107.1(4) . . ?
C32 C33 H33 126.5 . . ?
C34 C33 H33 126.5 . . ?
C35 C34 C33 107.9(4) . . ?
C35 C34 H34 126.0 . . ?
C33 C34 H34 126.0 . . ?
N7 C35 C34 107.8(3) . . ?
N7 C35 C36 121.5(3) . . ?
C34 C35 C36 130.2(3) . . ?
C41 C36 C35 110.8(3) . . ?
C41 C36 C39 109.8(3) . . ?
C35 C36 C39 108.9(3) . . ?
C41 C36 C37 108.8(3) . . ?
C35 C36 C37 107.3(3) . . ?
C39 C36 C37 111.2(3) . . ?
C38 C37 C36 115.3(3) . . ?
C38 C37 H37A 108.5 . . ?
C36 C37 H37A 108.5 . . ?
C38 C37 H37B 108.5 . . ?
C36 C37 H37B 108.5 . . ?
H37A C37 H37B 107.5 . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C40 C39 C36 114.9(3) . . ?
C40 C39 H39A 108.5 . . ?
C36 C39 H39A 108.5 . . ?
C40 C39 H39B 108.5 . . ?
C36 C39 H39B 108.5 . . ?
H39A C39 H39B 107.5 . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
N10 C41 C42 107.5(3) . . ?
N10 C41 C36 121.8(3) . . ?
C42 C41 C36 130.5(4) . . ?
C41 C42 C43 108.6(4) . . ?
C41 C42 H42 125.7 . . ?
C43 C42 H42 125.7 . . ?
C44 C43 C42 107.4(4) . . ?
C44 C43 H43 126.3 . . ?
C42 C43 H43 126.3 . . ?
N11 C44 C43 126.6(4) . . ?
N11 C44 N10 126.2(4) . . ?
C43 C44 N10 107.1(4) . . ?
C50 C45 C46 119.3(4) . . ?
C50 C45 N12 115.6(4) . . ?
C46 C45 N12 125.1(4) . . ?
C47 C46 C45 120.5(4) . . ?
C47 C46 H46 119.8 . . ?
C45 C46 H46 119.8 . . ?
C46 C47 C48 119.1(4) . . ?
C46 C47 H47 120.5 . . ?
C48 C47 H47 120.5 . . ?
C49 C48 C47 121.1(4) . . ?
C49 C48 Cl4 119.1(4) . . ?
C47 C48 Cl4 119.7(4) . . ?
C50 C49 C48 119.2(5) . . ?
C50 C49 H49 120.4 . . ?
C48 C49 H49 120.4 . . ?
C49 C50 C45 120.8(4) . . ?
C49 C50 H50 119.6 . . ?
C45 C50 H50 119.6 . . ?
Cl5 C51 Cl7 111.1(6) . . ?
Cl5 C51 Cl6 111.1(5) . . ?
Cl7 C51 Cl6 111.4(5) . . ?
Cl5 C51 H51 107.7 . . ?
Cl7 C51 H51 107.7 . . ?
Cl6 C51 H51 107.7 . . ?
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 C3 1.742(5) . ?
Cl2 C23 1.746(5) . ?
Cl3 C28 1.744(4) . ?
Cl4 C48 1.746(5) . ?
N1 C10 1.363(5) . ?
N1 C7 1.388(5) . ?
N1 H1' 0.8800 . ?
N2 N3 1.291(5) . ?
N2 C7 1.365(6) . ?
N3 C6 1.420(5) . ?
N4 C16 1.372(5) . ?
N4 C19 1.397(5) . ?
N4 H4' 0.8800 . ?
N5 N6 1.291(5) . ?
N5 C19 1.371(6) . ?
N6 C20 1.416(5) . ?
N7 C35 1.361(5) . ?
N7 C32 1.387(5) . ?
N7 H7' 0.8800 . ?
N8 N9 1.291(5) . ?
N8 C32 1.369(5) . ?
N9 C31 1.422(5) . ?
N10 C41 1.362(5) . ?
N10 C44 1.399(5) . ?
N10 H10' 0.8800 . ?
N11 N12 1.287(5) . ?
N11 C44 1.370(5) . ?
N12 C45 1.431(5) . ?
C1 C2 1.374(6) . ?
C1 C6 1.397(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.396(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(7) . ?
C4 C5 1.389(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.400(6) . ?
C5 H5 0.9500 . ?
C7 C8 1.398(6) . ?
C8 C9 1.403(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.402(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.516(6) . ?
C11 C16 1.527(6) . ?
C11 C12 1.555(6) . ?
C11 C14 1.562(6) . ?
C12 C13 1.514(6) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.524(7) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.403(6) . ?
C17 C18 1.395(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.391(6) . ?
C18 H18 0.9500 . ?
C20 C25 1.404(6) . ?
C20 C21 1.406(6) . ?
C21 C22 1.378(6) . ?
C21 H21 0.9500 . ?
C22 C23 1.402(7) . ?
C22 H22 0.9500 . ?
C23 C24 1.389(7) . ?
C24 C25 1.383(7) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 C27 1.396(6) . ?
C26 C31 1.398(6) . ?
C26 H26 0.9500 . ?
C27 C28 1.380(7) . ?
C27 H27 0.9500 . ?
C28 C29 1.389(7) . ?
C29 C30 1.389(6) . ?
C29 H29 0.9500 . ?
C30 C31 1.397(6) . ?
C30 H30 0.9500 . ?
C32 C33 1.396(6) . ?
C33 C34 1.404(6) . ?
C33 H33 0.9500 . ?
C34 C35 1.399(6) . ?
C34 H34 0.9500 . ?
C35 C36 1.520(5) . ?
C36 C41 1.516(5) . ?
C36 C39 1.553(5) . ?
C36 C37 1.562(5) . ?
C37 C38 1.526(5) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 C40 1.531(6) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C41 C42 1.391(6) . ?
C42 C43 1.395(6) . ?
C42 H42 0.9500 . ?
C43 C44 1.392(6) . ?
C43 H43 0.9500 . ?
C45 C50 1.395(6) . ?
C45 C46 1.404(6) . ?
C46 C47 1.383(7) . ?
C46 H46 0.9500 . ?
C47 C48 1.395(7) . ?
C47 H47 0.9500 . ?
C48 C49 1.395(7) . ?
C49 C50 1.378(7) . ?
C49 H49 0.9500 . ?
C50 H50 0.9500 . ?
C51 Cl5 1.749(10) . ?
C51 Cl7 1.758(11) . ?
C51 Cl6 1.759(10) . ?
C51 H51 1.0000 . ?
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
N10 H10' N6 0.88 2.16 3.009(5) 163.0 1_545
N7 H7' N3 0.88 2.16 3.009(5) 163.4 1_545
N4 H4' N12 0.88 2.19 3.043(5) 164.5 1_565
N1 H1' N9 0.88 2.12 2.982(5) 164.9 1_565
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
C7 N2 N3 C6 174.9(3) . . . . ?
C19 N5 N6 C20 175.6(3) . . . . ?
C32 N8 N9 C31 176.4(3) . . . . ?
C44 N11 N12 C45 -179.8(4) . . . . ?
C6 C1 C2 C3 -0.7(6) . . . . ?
C1 C2 C3 C4 -0.3(7) . . . . ?
C1 C2 C3 Cl1 178.9(3) . . . . ?
C2 C3 C4 C5 0.9(7) . . . . ?
Cl1 C3 C4 C5 -178.3(3) . . . . ?
C3 C4 C5 C6 -0.5(7) . . . . ?
C2 C1 C6 C5 1.1(6) . . . . ?
C2 C1 C6 N3 -178.4(4) . . . . ?
C4 C5 C6 C1 -0.5(6) . . . . ?
C4 C5 C6 N3 178.9(4) . . . . ?
N2 N3 C6 C1 -179.4(4) . . . . ?
N2 N3 C6 C5 1.1(6) . . . . ?
N3 N2 C7 N1 -10.3(6) . . . . ?
N3 N2 C7 C8 170.0(4) . . . . ?
C10 N1 C7 N2 -179.1(4) . . . . ?
C10 N1 C7 C8 0.6(5) . . . . ?
N2 C7 C8 C9 -179.3(4) . . . . ?
N1 C7 C8 C9 1.0(5) . . . . ?
C7 C8 C9 C10 -2.2(5) . . . . ?
C7 N1 C10 C9 -2.0(5) . . . . ?
C7 N1 C10 C11 173.5(4) . . . . ?
C8 C9 C10 N1 2.6(5) . . . . ?
C8 C9 C10 C11 -172.4(4) . . . . ?
N1 C10 C11 C16 55.9(5) . . . . ?
C9 C10 C11 C16 -129.7(5) . . . . ?
N1 C10 C11 C12 -63.0(5) . . . . ?
C9 C10 C11 C12 111.4(5) . . . . ?
N1 C10 C11 C14 175.5(4) . . . . ?
C9 C10 C11 C14 -10.2(6) . . . . ?
C10 C11 C12 C13 -55.4(5) . . . . ?
C16 C11 C12 C13 -175.3(4) . . . . ?
C14 C11 C12 C13 65.0(5) . . . . ?
C10 C11 C14 C15 -176.1(4) . . . . ?
C16 C11 C14 C15 -55.9(5) . . . . ?
C12 C11 C14 C15 63.5(6) . . . . ?
C19 N4 C16 C17 -1.0(5) . . . . ?
C19 N4 C16 C11 173.2(4) . . . . ?
C10 C11 C16 N4 50.5(5) . . . . ?
C12 C11 C16 N4 169.8(4) . . . . ?
C14 C11 C16 N4 -69.1(5) . . . . ?
C10 C11 C16 C17 -136.7(5) . . . . ?
C12 C11 C16 C17 -17.4(6) . . . . ?
C14 C11 C16 C17 103.7(5) . . . . ?
N4 C16 C17 C18 1.2(5) . . . . ?
C11 C16 C17 C18 -172.4(4) . . . . ?
C16 C17 C18 C19 -0.9(5) . . . . ?
N6 N5 C19 C18 168.7(4) . . . . ?
N6 N5 C19 N4 -9.8(6) . . . . ?
C17 C18 C19 N5 -178.5(4) . . . . ?
C17 C18 C19 N4 0.3(5) . . . . ?
C16 N4 C19 N5 179.2(4) . . . . ?
C16 N4 C19 C18 0.5(5) . . . . ?
N5 N6 C20 C25 179.5(4) . . . . ?
N5 N6 C20 C21 -1.8(6) . . . . ?
C25 C20 C21 C22 -0.7(6) . . . . ?
N6 C20 C21 C22 -179.3(4) . . . . ?
C20 C21 C22 C23 0.1(7) . . . . ?
C21 C22 C23 C24 0.7(7) . . . . ?
C21 C22 C23 Cl2 178.5(3) . . . . ?
C22 C23 C24 C25 -0.9(7) . . . . ?
Cl2 C23 C24 C25 -178.8(4) . . . . ?
C23 C24 C25 C20 0.4(7) . . . . ?
C21 C20 C25 C24 0.4(7) . . . . ?
N6 C20 C25 C24 179.2(4) . . . . ?
C31 C26 C27 C28 0.4(6) . . . . ?
C26 C27 C28 C29 -0.3(7) . . . . ?
C26 C27 C28 Cl3 179.5(3) . . . . ?
C27 C28 C29 C30 0.3(7) . . . . ?
Cl3 C28 C29 C30 -179.4(4) . . . . ?
C28 C29 C30 C31 -0.5(7) . . . . ?
C29 C30 C31 C26 0.6(7) . . . . ?
C29 C30 C31 N9 179.4(4) . . . . ?
C27 C26 C31 C30 -0.5(6) . . . . ?
C27 C26 C31 N9 -179.2(4) . . . . ?
N8 N9 C31 C30 -175.2(4) . . . . ?
N8 N9 C31 C26 3.5(6) . . . . ?
N9 N8 C32 N7 -10.5(6) . . . . ?
N9 N8 C32 C33 169.8(4) . . . . ?
C35 N7 C32 N8 -179.0(4) . . . . ?
C35 N7 C32 C33 0.7(4) . . . . ?
N8 C32 C33 C34 -179.9(4) . . . . ?
N7 C32 C33 C34 0.4(5) . . . . ?
C32 C33 C34 C35 -1.4(5) . . . . ?
C32 N7 C35 C34 -1.6(4) . . . . ?
C32 N7 C35 C36 170.8(3) . . . . ?
C33 C34 C35 N7 1.8(5) . . . . ?
C33 C34 C35 C36 -169.7(4) . . . . ?
N7 C35 C36 C41 54.8(5) . . . . ?
C34 C35 C36 C41 -134.6(4) . . . . ?
N7 C35 C36 C39 175.7(3) . . . . ?
C34 C35 C36 C39 -13.8(6) . . . . ?
N7 C35 C36 C37 -63.9(4) . . . . ?
C34 C35 C36 C37 106.6(5) . . . . ?
C41 C36 C37 C38 -171.0(3) . . . . ?
C35 C36 C37 C38 -50.9(4) . . . . ?
C39 C36 C37 C38 68.0(4) . . . . ?
C41 C36 C39 C40 -53.1(5) . . . . ?
C35 C36 C39 C40 -174.7(3) . . . . ?
C37 C36 C39 C40 67.3(4) . . . . ?
C44 N10 C41 C42 -1.0(4) . . . . ?
C44 N10 C41 C36 174.9(3) . . . . ?
C35 C36 C41 N10 50.9(5) . . . . ?
C39 C36 C41 N10 -69.4(4) . . . . ?
C37 C36 C41 N10 168.7(3) . . . . ?
C35 C36 C41 C42 -134.3(4) . . . . ?
C39 C36 C41 C42 105.4(5) . . . . ?
C37 C36 C41 C42 -16.4(6) . . . . ?
N10 C41 C42 C43 1.4(5) . . . . ?
C36 C41 C42 C43 -174.0(4) . . . . ?
C41 C42 C43 C44 -1.2(5) . . . . ?
N12 N11 C44 C43 169.2(4) . . . . ?
N12 N11 C44 N10 -7.3(6) . . . . ?
C42 C43 C44 N11 -176.4(4) . . . . ?
C42 C43 C44 N10 0.6(5) . . . . ?
C41 N10 C44 N11 177.3(4) . . . . ?
C41 N10 C44 C43 0.3(5) . . . . ?
N11 N12 C45 C50 180.0(4) . . . . ?
N11 N12 C45 C46 2.0(6) . . . . ?
C50 C45 C46 C47 -2.2(7) . . . . ?
N12 C45 C46 C47 175.8(4) . . . . ?
C45 C46 C47 C48 1.0(7) . . . . ?
C46 C47 C48 C49 0.7(8) . . . . ?
C46 C47 C48 Cl4 179.4(4) . . . . ?
C47 C48 C49 C50 -1.2(8) . . . . ?
Cl4 C48 C49 C50 -179.9(4) . . . . ?
C48 C49 C50 C45 0.0(8) . . . . ?
C46 C45 C50 C49 1.7(7) . . . . ?
N12 C45 C50 C49 -176.5(4) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653612
