#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/11/7201169.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_7201169
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_sum            'C51 H49 Br4 Cl3 N12'
_chemical_formula_weight         1256.01
_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                97.289(4)
_cell_angle_beta                 103.462(3)
_cell_angle_gamma                107.880(3)
_cell_formula_units_Z            2
_cell_length_a                   12.2064(19)
_cell_length_b                   14.770(2)
_cell_length_c                   17.428(3)
_cell_measurement_reflns_used    2011
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      18.62
_cell_measurement_theta_min      2.16
_cell_volume                     2840.6(8)
_computing_cell_refinement       'Bruker SMART APEX II'
_computing_data_collection       'Bruker SMART APEX II'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'APEX II CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_sigmaI/netI    0.0970
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14654
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.48
_exptl_absorpt_coefficient_mu    3.020
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.641066
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            ORANGE
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1260
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.762
_refine_diff_density_min         -0.681
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     630
_refine_ls_number_reflns         9981
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.1717
_refine_ls_R_factor_gt           0.0650
_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)+(0.0812P)²+2.4936P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1565
_refine_ls_wR_factor_ref         0.2029
_reflns_number_gt                4267
_reflns_number_total             9981
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b905568a.txt
_cod_data_source_block           071209a
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed
to 'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'NONE' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7201169
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
Br1 Br 0.17957(10) -0.11576(7) 0.04653(7) 0.1090(4) Uani 1 1 d . . .
Br2 Br 0.88804(10) 0.96688(10) 0.16665(8) 0.1414(5) Uani 1 1 d . . .
Br3 Br -0.52358(7) 0.10198(7) 0.12045(8) 0.1141(4) Uani 1 1 d . . .
Br4 Br 0.41917(14) 0.99236(8) 0.66393(7) 0.1425(5) Uani 1 1 d . . .
N1 N 0.1403(4) 0.4138(4) 0.3066(3) 0.0498(14) Uani 1 1 d . . .
H1' H 0.1063 0.4007 0.2554 0.060 Uiso 1 1 calc R . .
N2 N 0.2151(5) 0.2782(4) 0.3118(4) 0.0599(15) Uani 1 1 d . . .
N3 N 0.1827(5) 0.2613(4) 0.2350(4) 0.0546(14) Uani 1 1 d . . .
N4 N 0.2208(5) 0.6408(4) 0.2656(3) 0.0509(14) Uani 1 1 d . . .
H4' H 0.2827 0.6428 0.3024 0.061 Uiso 1 1 calc R . .
N5 N 0.3245(5) 0.7324(4) 0.1800(3) 0.0598(15) Uani 1 1 d . . .
N6 N 0.4231(5) 0.7297(4) 0.2245(3) 0.0530(14) Uani 1 1 d . . .
N7 N 0.2158(4) 0.4135(3) 0.1304(3) 0.0397(12) Uani 1 1 d . . .
H7' H 0.2113 0.3790 0.1665 0.048 Uiso 1 1 calc R . .
N8 N 0.0015(4) 0.3817(4) 0.0754(3) 0.0483(13) Uani 1 1 d . . .
N9 N -0.0139(4) 0.3389(4) 0.1330(3) 0.0465(13) Uani 1 1 d . . .
N10 N 0.4570(4) 0.5549(4) 0.2881(3) 0.0442(13) Uani 1 1 d . . .
H10' H 0.4331 0.5979 0.2674 0.053 Uiso 1 1 calc R . .
N11 N 0.4961(5) 0.6259(4) 0.4315(3) 0.0551(15) Uani 1 1 d . . .
N12 N 0.4476(5) 0.6858(4) 0.4081(3) 0.0572(15) Uani 1 1 d . . .
C1 C 0.1448(6) 0.1491(5) 0.1122(5) 0.063(2) Uani 1 1 d . . .
H1 H 0.1188 0.1925 0.0851 0.076 Uiso 1 1 calc R . .
C2 C 0.1432(6) 0.0643(5) 0.0684(5) 0.066(2) Uani 1 1 d . . .
H2 H 0.1165 0.0508 0.0123 0.079 Uiso 1 1 calc R . .
C3 C 0.1809(6) 0.0000(5) 0.1073(6) 0.067(2) Uani 1 1 d . . .
C4 C 0.2213(7) 0.0179(6) 0.1905(6) 0.077(2) Uani 1 1 d . . .
H4 H 0.2465 -0.0266 0.2164 0.092 Uiso 1 1 calc R . .
C5 C 0.2233(6) 0.1043(6) 0.2351(5) 0.067(2) Uani 1 1 d . . .
H5 H 0.2507 0.1177 0.2912 0.081 Uiso 1 1 calc R . .
C6 C 0.1843(5) 0.1711(5) 0.1956(4) 0.0516(17) Uani 1 1 d . . .
C7 C 0.2013(6) 0.3611(5) 0.3459(4) 0.0528(17) Uani 1 1 d . . .
C8 C 0.2425(7) 0.4058(6) 0.4270(4) 0.071(2) Uani 1 1 d . . .
H8 H 0.2858 0.3857 0.4685 0.085 Uiso 1 1 calc R . .
C9 C 0.2072(7) 0.4860(6) 0.4345(4) 0.069(2) Uani 1 1 d . . .
H9 H 0.2251 0.5305 0.4824 0.082 Uiso 1 1 calc R . .
C10 C 0.1412(6) 0.4897(5) 0.3600(4) 0.0519(17) Uani 1 1 d . . .
C11 C 0.0712(6) 0.5536(5) 0.3340(4) 0.0554(18) Uani 1 1 d . . .
C12 C -0.0635(6) 0.4929(6) 0.3064(5) 0.073(2) Uani 1 1 d . . .
H12A H -0.1080 0.5358 0.2929 0.087 Uiso 1 1 calc R . .
H12B H -0.0799 0.4456 0.2574 0.087 Uiso 1 1 calc R . .
C13 C -0.1114(8) 0.4387(8) 0.3676(5) 0.117(4) Uani 1 1 d . . .
H13A H -0.0656 0.3982 0.3837 0.175 Uiso 1 1 calc R . .
H13B H -0.1943 0.3989 0.3435 0.175 Uiso 1 1 calc R . .
H13C H -0.1041 0.4849 0.4142 0.175 Uiso 1 1 calc R . .
C14 C 0.1006(7) 0.6394(6) 0.4068(5) 0.082(2) Uani 1 1 d . . .
H14A H 0.0750 0.6126 0.4504 0.099 Uiso 1 1 calc R . .
H14B H 0.1870 0.6723 0.4261 0.099 Uiso 1 1 calc R . .
C15 C 0.0412(10) 0.7149(8) 0.3872(6) 0.145(5) Uani 1 1 d . . .
H15A H 0.0681 0.7438 0.3455 0.217 Uiso 1 1 calc R . .
H15B H 0.0629 0.7647 0.4348 0.217 Uiso 1 1 calc R . .
H15C H -0.0446 0.6835 0.3690 0.217 Uiso 1 1 calc R . .
C16 C 0.1035(6) 0.5963(5) 0.2642(4) 0.0533(17) Uani 1 1 d . . .
C17 C 0.0329(7) 0.6084(6) 0.1954(5) 0.071(2) Uani 1 1 d . . .
H17 H -0.0507 0.5846 0.1788 0.086 Uiso 1 1 calc R . .
C18 C 0.1050(7) 0.6613(6) 0.1548(5) 0.080(2) Uani 1 1 d . . .
H18 H 0.0791 0.6798 0.1067 0.096 Uiso 1 1 calc R . .
C19 C 0.2243(6) 0.6820(5) 0.1990(4) 0.0559(18) Uani 1 1 d . . .
C20 C 0.5284(6) 0.7871(5) 0.2067(4) 0.0520(17) Uani 1 1 d . . .
C21 C 0.5291(7) 0.8458(5) 0.1505(4) 0.065(2) Uani 1 1 d . . .
H21 H 0.4570 0.8494 0.1211 0.078 Uiso 1 1 calc R . .
C22 C 0.6354(8) 0.8988(6) 0.1379(5) 0.078(2) Uani 1 1 d . . .
H22 H 0.6354 0.9378 0.1000 0.094 Uiso 1 1 calc R . .
C23 C 0.7419(8) 0.8933(6) 0.1822(6) 0.081(2) Uani 1 1 d . . .
C24 C 0.7435(7) 0.8370(6) 0.2390(6) 0.087(3) Uani 1 1 d . . .
H24 H 0.8157 0.8343 0.2690 0.104 Uiso 1 1 calc R . .
C25 C 0.6357(7) 0.7842(6) 0.2511(5) 0.077(2) Uani 1 1 d . . .
H25 H 0.6361 0.7462 0.2898 0.092 Uiso 1 1 calc R . .
C26 C -0.2346(6) 0.2888(5) 0.0678(4) 0.0533(18) Uani 1 1 d . . .
H26 H -0.2238 0.3276 0.0301 0.064 Uiso 1 1 calc R . .
C27 C -0.3492(6) 0.2326(5) 0.0663(5) 0.0594(19) Uani 1 1 d . . .
H27 H -0.4154 0.2316 0.0264 0.071 Uiso 1 1 calc R . .
C28 C -0.3651(6) 0.1781(5) 0.1239(5) 0.068(2) Uani 1 1 d . . .
C29 C -0.2699(7) 0.1749(6) 0.1828(5) 0.082(2) Uani 1 1 d . . .
H29 H -0.2820 0.1370 0.2209 0.099 Uiso 1 1 calc R . .
C30 C -0.1560(6) 0.2301(6) 0.1831(5) 0.072(2) Uani 1 1 d . . .
H30 H -0.0904 0.2296 0.2226 0.086 Uiso 1 1 calc R . .
C31 C -0.1354(5) 0.2873(4) 0.1257(4) 0.0461(16) Uani 1 1 d . . .
C32 C 0.1187(5) 0.4249(5) 0.0777(4) 0.0449(16) Uani 1 1 d . . .
C33 C 0.1644(6) 0.4861(5) 0.0310(4) 0.0593(19) Uani 1 1 d . . .
H33 H 0.1201 0.5068 -0.0096 0.071 Uiso 1 1 calc R . .
C34 C 0.2876(5) 0.5117(5) 0.0548(4) 0.0533(18) Uani 1 1 d . . .
H34 H 0.3406 0.5533 0.0332 0.064 Uiso 1 1 calc R . .
C35 C 0.3193(5) 0.4656(4) 0.1157(3) 0.0370(14) Uani 1 1 d . . .
C36 C 0.4380(5) 0.4545(4) 0.1544(4) 0.0398(15) Uani 1 1 d . . .
C37 C 0.4291(6) 0.3488(5) 0.1236(4) 0.0542(18) Uani 1 1 d . . .
H37A H 0.5074 0.3435 0.1437 0.065 Uiso 1 1 calc R . .
H37B H 0.3740 0.3054 0.1463 0.065 Uiso 1 1 calc R . .
C38 C 0.3863(7) 0.3141(5) 0.0311(4) 0.073(2) Uani 1 1 d . . .
H38A H 0.3094 0.3201 0.0104 0.110 Uiso 1 1 calc R . .
H38B H 0.3795 0.2472 0.0171 0.110 Uiso 1 1 calc R . .
H38C H 0.4434 0.3533 0.0082 0.110 Uiso 1 1 calc R . .
C39 C 0.5383(5) 0.5293(5) 0.1312(4) 0.0543(18) Uani 1 1 d . . .
H39A H 0.5231 0.5138 0.0730 0.065 Uiso 1 1 calc R . .
H39B H 0.5340 0.5935 0.1456 0.065 Uiso 1 1 calc R . .
C40 C 0.6663(6) 0.5328(6) 0.1717(5) 0.085(3) Uani 1 1 d . . .
H40A H 0.6833 0.5500 0.2293 0.128 Uiso 1 1 calc R . .
H40B H 0.7232 0.5804 0.1543 0.128 Uiso 1 1 calc R . .
H40C H 0.6722 0.4700 0.1568 0.128 Uiso 1 1 calc R . .
C41 C 0.4642(5) 0.4740(5) 0.2455(4) 0.0469(16) Uani 1 1 d . . .
C42 C 0.5068(6) 0.4247(5) 0.3011(4) 0.0595(19) Uani 1 1 d . . .
H42 H 0.5205 0.3667 0.2890 0.071 Uiso 1 1 calc R . .
C43 C 0.5255(7) 0.4765(5) 0.3779(4) 0.068(2) Uani 1 1 d . . .
H43 H 0.5541 0.4595 0.4262 0.082 Uiso 1 1 calc R . .
C44 C 0.4945(6) 0.5570(5) 0.3701(4) 0.0517(17) Uani 1 1 d . . .
C45 C 0.4491(6) 0.7581(5) 0.4719(4) 0.0578(18) Uani 1 1 d . . .
C46 C 0.4014(7) 0.8277(6) 0.4484(5) 0.077(2) Uani 1 1 d . . .
H46 H 0.3753 0.8279 0.3939 0.092 Uiso 1 1 calc R . .
C47 C 0.3927(8) 0.8964(6) 0.5056(6) 0.089(3) Uani 1 1 d . . .
H47 H 0.3607 0.9429 0.4896 0.107 Uiso 1 1 calc R . .
C48 C 0.4311(9) 0.8963(6) 0.5857(6) 0.089(3) Uani 1 1 d . . .
C49 C 0.4799(8) 0.8305(7) 0.6108(5) 0.089(3) Uani 1 1 d . . .
H49 H 0.5067 0.8323 0.6657 0.107 Uiso 1 1 calc R . .
C50 C 0.4899(7) 0.7610(6) 0.5548(5) 0.075(2) Uani 1 1 d . . .
H50 H 0.5237 0.7159 0.5720 0.090 Uiso 1 1 calc R . .
Cl1 Cl 0.8077(6) 0.8296(6) 0.4730(4) 0.349(4) Uani 1 1 d . . .
Cl2 Cl 1.0238(6) 0.8847(6) 0.5939(4) 0.297(3) Uani 1 1 d . . .
Cl3 Cl 0.8787(7) 0.9987(5) 0.5960(4) 0.309(3) Uani 1 1 d . . .
C51 C 0.8799(16) 0.8790(12) 0.5685(11) 0.199(6) Uiso 1 1 d . . .
H51 H 0.8387 0.8388 0.6011 0.238 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'
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'
Br Br -0.2901 2.4595 '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 110.3(5) . . ?
C10 N1 H1' 124.8 . . ?
C7 N1 H1' 124.8 . . ?
N3 N2 C7 112.6(6) . . ?
N2 N3 C6 115.3(6) . . ?
C16 N4 C19 109.7(5) . . ?
C16 N4 H4' 125.2 . . ?
C19 N4 H4' 125.2 . . ?
N6 N5 C19 114.4(6) . . ?
N5 N6 C20 113.8(6) . . ?
C35 N7 C32 109.2(5) . . ?
C35 N7 H7' 125.4 . . ?
C32 N7 H7' 125.4 . . ?
N9 N8 C32 114.8(5) . . ?
N8 N9 C31 114.0(5) . . ?
C41 N10 C44 109.1(5) . . ?
C41 N10 H10' 125.4 . . ?
C44 N10 H10' 125.4 . . ?
N12 N11 C44 114.3(5) . . ?
N11 N12 C45 114.6(6) . . ?
C2 C1 C6 121.2(7) . . ?
C2 C1 H1 119.4 . . ?
C6 C1 H1 119.4 . . ?
C3 C2 C1 119.9(7) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 121.5(7) . . ?
C2 C3 Br1 119.6(7) . . ?
C4 C3 Br1 118.9(6) . . ?
C3 C4 C5 118.6(7) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C4 C5 C6 120.4(7) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 118.3(7) . . ?
C1 C6 N3 116.5(6) . . ?
C5 C6 N3 125.1(7) . . ?
N2 C7 N1 126.5(6) . . ?
N2 C7 C8 126.5(7) . . ?
N1 C7 C8 107.0(6) . . ?
C9 C8 C7 107.0(6) . . ?
C9 C8 H8 126.5 . . ?
C7 C8 H8 126.5 . . ?
C10 C9 C8 109.3(7) . . ?
C10 C9 H9 125.3 . . ?
C8 C9 H9 125.3 . . ?
N1 C10 C9 106.3(6) . . ?
N1 C10 C11 121.2(6) . . ?
C9 C10 C11 132.3(7) . . ?
C10 C11 C16 111.7(5) . . ?
C10 C11 C12 109.2(6) . . ?
C16 C11 C12 108.1(6) . . ?
C10 C11 C14 108.7(6) . . ?
C16 C11 C14 108.3(6) . . ?
C12 C11 C14 110.8(6) . . ?
C13 C12 C11 115.6(6) . . ?
C13 C12 H12A 108.4 . . ?
C11 C12 H12A 108.4 . . ?
C13 C12 H12B 108.4 . . ?
C11 C12 H12B 108.4 . . ?
H12A C12 H12B 107.5 . . ?
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 114.5(7) . . ?
C15 C14 H14A 108.6 . . ?
C11 C14 H14A 108.6 . . ?
C15 C14 H14B 108.6 . . ?
C11 C14 H14B 108.6 . . ?
H14A C14 H14B 107.6 . . ?
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 . . ?
C17 C16 N4 106.9(6) . . ?
C17 C16 C11 131.0(6) . . ?
N4 C16 C11 121.8(6) . . ?
C16 C17 C18 109.3(7) . . ?
C16 C17 H17 125.3 . . ?
C18 C17 H17 125.3 . . ?
C17 C18 C19 107.5(7) . . ?
C17 C18 H18 126.3 . . ?
C19 C18 H18 126.3 . . ?
N5 C19 N4 126.6(6) . . ?
N5 C19 C18 126.8(7) . . ?
N4 C19 C18 106.6(6) . . ?
C25 C20 C21 119.1(7) . . ?
C25 C20 N6 115.9(7) . . ?
C21 C20 N6 125.0(6) . . ?
C22 C21 C20 120.7(7) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C21 C22 C23 119.2(8) . . ?
C21 C22 H22 120.4 . . ?
C23 C22 H22 120.4 . . ?
C24 C23 C22 121.1(8) . . ?
C24 C23 Br2 119.3(7) . . ?
C22 C23 Br2 119.6(7) . . ?
C23 C24 C25 119.0(8) . . ?
C23 C24 H24 120.5 . . ?
C25 C24 H24 120.5 . . ?
C20 C25 C24 120.9(8) . . ?
C20 C25 H25 119.5 . . ?
C24 C25 H25 119.5 . . ?
C27 C26 C31 119.9(6) . . ?
C27 C26 H26 120.1 . . ?
C31 C26 H26 120.1 . . ?
C28 C27 C26 119.9(6) . . ?
C28 C27 H27 120.1 . . ?
C26 C27 H27 120.1 . . ?
C27 C28 C29 122.3(6) . . ?
C27 C28 Br3 118.9(6) . . ?
C29 C28 Br3 118.8(6) . . ?
C28 C29 C30 117.4(7) . . ?
C28 C29 H29 121.3 . . ?
C30 C29 H29 121.3 . . ?
C29 C30 C31 122.3(7) . . ?
C29 C30 H30 118.8 . . ?
C31 C30 H30 118.8 . . ?
C26 C31 C30 118.2(6) . . ?
C26 C31 N9 125.9(6) . . ?
C30 C31 N9 115.9(6) . . ?
N8 C32 C33 128.5(6) . . ?
N8 C32 N7 124.6(6) . . ?
C33 C32 N7 106.9(5) . . ?
C32 C33 C34 108.0(5) . . ?
C32 C33 H33 126.0 . . ?
C34 C33 H33 126.0 . . ?
C35 C34 C33 108.8(5) . . ?
C35 C34 H34 125.6 . . ?
C33 C34 H34 125.6 . . ?
N7 C35 C34 107.0(5) . . ?
N7 C35 C36 121.2(5) . . ?
C34 C35 C36 131.1(5) . . ?
C35 C36 C41 110.3(5) . . ?
C35 C36 C39 108.2(5) . . ?
C41 C36 C39 109.4(5) . . ?
C35 C36 C37 108.5(5) . . ?
C41 C36 C37 108.8(5) . . ?
C39 C36 C37 111.6(5) . . ?
C38 C37 C36 114.7(5) . . ?
C38 C37 H37A 108.6 . . ?
C36 C37 H37A 108.6 . . ?
C38 C37 H37B 108.6 . . ?
C36 C37 H37B 108.6 . . ?
H37A C37 H37B 107.6 . . ?
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 114.4(6) . . ?
C40 C39 H39A 108.7 . . ?
C36 C39 H39A 108.7 . . ?
C40 C39 H39B 108.7 . . ?
C36 C39 H39B 108.7 . . ?
H39A C39 H39B 107.6 . . ?
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 107.1(6) . . ?
N10 C41 C36 121.9(5) . . ?
C42 C41 C36 130.7(6) . . ?
C41 C42 C43 108.3(6) . . ?
C41 C42 H42 125.8 . . ?
C43 C42 H42 125.8 . . ?
C44 C43 C42 107.9(6) . . ?
C44 C43 H43 126.0 . . ?
C42 C43 H43 126.0 . . ?
C43 C44 N11 126.6(6) . . ?
C43 C44 N10 107.5(6) . . ?
N11 C44 N10 125.9(6) . . ?
C46 C45 C50 118.5(7) . . ?
C46 C45 N12 116.3(6) . . ?
C50 C45 N12 125.2(7) . . ?
C47 C46 C45 120.2(8) . . ?
C47 C46 H46 119.9 . . ?
C45 C46 H46 119.9 . . ?
C48 C47 C46 120.0(8) . . ?
C48 C47 H47 120.0 . . ?
C46 C47 H47 120.0 . . ?
C49 C48 C47 121.4(8) . . ?
C49 C48 Br4 119.2(7) . . ?
C47 C48 Br4 119.4(8) . . ?
C48 C49 C50 119.8(8) . . ?
C48 C49 H49 120.1 . . ?
C50 C49 H49 120.1 . . ?
C49 C50 C45 120.1(8) . . ?
C49 C50 H50 120.0 . . ?
C45 C50 H50 120.0 . . ?
Cl1 C51 Cl2 113.5(11) . . ?
Cl1 C51 Cl3 111.9(11) . . ?
Cl2 C51 Cl3 107.9(10) . . ?
Cl1 C51 H51 107.8 . . ?
Cl2 C51 H51 107.8 . . ?
Cl3 C51 H51 107.8 . . ?
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
Br1 C3 1.887(7) . ?
Br2 C23 1.883(8) . ?
Br3 C28 1.899(7) . ?
Br4 C48 1.903(8) . ?
N1 C10 1.358(8) . ?
N1 C7 1.372(8) . ?
N1 H1' 0.8600 . ?
N2 N3 1.272(7) . ?
N2 C7 1.368(8) . ?
N3 C6 1.428(8) . ?
N4 C16 1.373(8) . ?
N4 C19 1.380(8) . ?
N4 H4' 0.8600 . ?
N5 N6 1.285(7) . ?
N5 C19 1.361(8) . ?
N6 C20 1.433(8) . ?
N7 C35 1.363(7) . ?
N7 C32 1.390(7) . ?
N7 H7' 0.8600 . ?
N8 N9 1.272(6) . ?
N8 C32 1.364(7) . ?
N9 C31 1.411(7) . ?
N10 C41 1.363(7) . ?
N10 C44 1.389(7) . ?
N10 H10' 0.8600 . ?
N11 N12 1.264(7) . ?
N11 C44 1.373(8) . ?
N12 C45 1.434(8) . ?
C1 C2 1.374(9) . ?
C1 C6 1.382(9) . ?
C1 H1 0.9300 . ?
C2 C3 1.364(10) . ?
C2 H2 0.9300 . ?
C3 C4 1.381(10) . ?
C4 C5 1.397(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.408(9) . ?
C5 H5 0.9300 . ?
C7 C8 1.384(9) . ?
C8 C9 1.381(9) . ?
C8 H8 0.9300 . ?
C9 C10 1.377(9) . ?
C9 H9 0.9300 . ?
C10 C11 1.500(9) . ?
C11 C16 1.516(9) . ?
C11 C12 1.535(9) . ?
C11 C14 1.564(9) . ?
C12 C13 1.531(10) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.539(11) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.371(9) . ?
C17 C18 1.377(10) . ?
C17 H17 0.9300 . ?
C18 C19 1.397(9) . ?
C18 H18 0.9300 . ?
C20 C25 1.374(9) . ?
C20 C21 1.387(9) . ?
C21 C22 1.378(10) . ?
C21 H21 0.9300 . ?
C22 C23 1.381(11) . ?
C22 H22 0.9300 . ?
C23 C24 1.372(11) . ?
C24 C25 1.387(10) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 C27 1.382(8) . ?
C26 C31 1.392(8) . ?
C26 H26 0.9300 . ?
C27 C28 1.376(10) . ?
C27 H27 0.9300 . ?
C28 C29 1.377(10) . ?
C29 C30 1.377(9) . ?
C29 H29 0.9300 . ?
C30 C31 1.406(9) . ?
C30 H30 0.9300 . ?
C32 C33 1.371(8) . ?
C33 C34 1.377(8) . ?
C33 H33 0.9300 . ?
C34 C35 1.377(8) . ?
C34 H34 0.9300 . ?
C35 C36 1.516(8) . ?
C36 C41 1.516(8) . ?
C36 C39 1.547(8) . ?
C36 C37 1.547(8) . ?
C37 C38 1.538(9) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 C40 1.540(8) . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C41 C42 1.384(8) . ?
C42 C43 1.386(9) . ?
C42 H42 0.9300 . ?
C43 C44 1.366(9) . ?
C43 H43 0.9300 . ?
C45 C46 1.388(9) . ?
C45 C50 1.405(9) . ?
C46 C47 1.375(10) . ?
C46 H46 0.9300 . ?
C47 C48 1.366(11) . ?
C47 H47 0.9300 . ?
C48 C49 1.354(11) . ?
C49 C50 1.378(10) . ?
C49 H49 0.9300 . ?
C50 H50 0.9300 . ?
Cl1 C51 1.641(17) . ?
Cl2 C51 1.680(17) . ?
Cl3 C51 1.778(16) . ?
C51 H51 0.9800 . ?
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 -174.4(5) . . . . ?
C19 N5 N6 C20 -177.0(5) . . . . ?
C32 N8 N9 C31 -174.5(5) . . . . ?
C44 N11 N12 C45 -179.9(5) . . . . ?
C6 C1 C2 C3 0.2(11) . . . . ?
C1 C2 C3 C4 -0.1(11) . . . . ?
C1 C2 C3 Br1 -179.5(5) . . . . ?
C2 C3 C4 C5 -0.2(11) . . . . ?
Br1 C3 C4 C5 179.3(5) . . . . ?
C3 C4 C5 C6 0.4(11) . . . . ?
C2 C1 C6 C5 0.0(10) . . . . ?
C2 C1 C6 N3 179.7(6) . . . . ?
C4 C5 C6 C1 -0.3(10) . . . . ?
C4 C5 C6 N3 -179.9(6) . . . . ?
N2 N3 C6 C1 177.4(6) . . . . ?
N2 N3 C6 C5 -2.9(9) . . . . ?
N3 N2 C7 N1 11.4(9) . . . . ?
N3 N2 C7 C8 -171.0(7) . . . . ?
C10 N1 C7 N2 177.7(6) . . . . ?
C10 N1 C7 C8 -0.3(7) . . . . ?
N2 C7 C8 C9 -179.1(7) . . . . ?
N1 C7 C8 C9 -1.1(8) . . . . ?
C7 C8 C9 C10 2.1(9) . . . . ?
C7 N1 C10 C9 1.6(7) . . . . ?
C7 N1 C10 C11 -174.3(6) . . . . ?
C8 C9 C10 N1 -2.3(8) . . . . ?
C8 C9 C10 C11 172.9(7) . . . . ?
N1 C10 C11 C16 -55.0(8) . . . . ?
C9 C10 C11 C16 130.4(8) . . . . ?
N1 C10 C11 C12 64.5(8) . . . . ?
C9 C10 C11 C12 -110.1(9) . . . . ?
N1 C10 C11 C14 -174.5(6) . . . . ?
C9 C10 C11 C14 10.8(11) . . . . ?
C10 C11 C12 C13 54.7(9) . . . . ?
C16 C11 C12 C13 176.4(7) . . . . ?
C14 C11 C12 C13 -65.0(9) . . . . ?
C10 C11 C14 C15 176.2(8) . . . . ?
C16 C11 C14 C15 54.5(9) . . . . ?
C12 C11 C14 C15 -63.9(9) . . . . ?
C19 N4 C16 C17 0.9(7) . . . . ?
C19 N4 C16 C11 -173.6(6) . . . . ?
C10 C11 C16 C17 137.9(8) . . . . ?
C12 C11 C16 C17 17.8(10) . . . . ?
C14 C11 C16 C17 -102.3(9) . . . . ?
C10 C11 C16 N4 -49.0(8) . . . . ?
C12 C11 C16 N4 -169.1(6) . . . . ?
C14 C11 C16 N4 70.8(8) . . . . ?
N4 C16 C17 C18 -1.0(9) . . . . ?
C11 C16 C17 C18 172.9(7) . . . . ?
C16 C17 C18 C19 0.6(9) . . . . ?
N6 N5 C19 N4 8.8(10) . . . . ?
N6 N5 C19 C18 -170.8(7) . . . . ?
C16 N4 C19 N5 179.8(6) . . . . ?
C16 N4 C19 C18 -0.6(8) . . . . ?
C17 C18 C19 N5 179.6(7) . . . . ?
C17 C18 C19 N4 -0.1(9) . . . . ?
N5 N6 C20 C25 -178.1(6) . . . . ?
N5 N6 C20 C21 3.7(9) . . . . ?
C25 C20 C21 C22 1.5(11) . . . . ?
N6 C20 C21 C22 179.7(6) . . . . ?
C20 C21 C22 C23 -0.3(11) . . . . ?
C21 C22 C23 C24 -0.8(13) . . . . ?
C21 C22 C23 Br2 -179.0(6) . . . . ?
C22 C23 C24 C25 0.8(13) . . . . ?
Br2 C23 C24 C25 179.0(6) . . . . ?
C21 C20 C25 C24 -1.6(12) . . . . ?
N6 C20 C25 C24 -179.9(7) . . . . ?
C23 C24 C25 C20 0.5(13) . . . . ?
C31 C26 C27 C28 2.4(10) . . . . ?
C26 C27 C28 C29 -1.9(12) . . . . ?
C26 C27 C28 Br3 179.8(5) . . . . ?
C27 C28 C29 C30 0.9(13) . . . . ?
Br3 C28 C29 C30 179.3(6) . . . . ?
C28 C29 C30 C31 -0.6(12) . . . . ?
C27 C26 C31 C30 -2.1(10) . . . . ?
C27 C26 C31 N9 178.4(6) . . . . ?
C29 C30 C31 C26 1.2(11) . . . . ?
C29 C30 C31 N9 -179.2(7) . . . . ?
N8 N9 C31 C26 -7.2(9) . . . . ?
N8 N9 C31 C30 173.3(6) . . . . ?
N9 N8 C32 C33 -170.9(7) . . . . ?
N9 N8 C32 N7 9.0(9) . . . . ?
C35 N7 C32 N8 179.3(6) . . . . ?
C35 N7 C32 C33 -0.8(7) . . . . ?
N8 C32 C33 C34 179.9(6) . . . . ?
N7 C32 C33 C34 0.0(8) . . . . ?
C32 C33 C34 C35 0.8(8) . . . . ?
C32 N7 C35 C34 1.3(7) . . . . ?
C32 N7 C35 C36 -170.1(5) . . . . ?
C33 C34 C35 N7 -1.3(7) . . . . ?
C33 C34 C35 C36 168.9(6) . . . . ?
N7 C35 C36 C41 -55.7(7) . . . . ?
C34 C35 C36 C41 135.2(7) . . . . ?
N7 C35 C36 C39 -175.4(5) . . . . ?
C34 C35 C36 C39 15.6(9) . . . . ?
N7 C35 C36 C37 63.4(7) . . . . ?
C34 C35 C36 C37 -105.6(7) . . . . ?
C35 C36 C37 C38 52.3(7) . . . . ?
C41 C36 C37 C38 172.3(5) . . . . ?
C39 C36 C37 C38 -66.8(7) . . . . ?
C35 C36 C39 C40 175.3(6) . . . . ?
C41 C36 C39 C40 55.1(7) . . . . ?
C37 C36 C39 C40 -65.4(7) . . . . ?
C44 N10 C41 C42 -0.1(7) . . . . ?
C44 N10 C41 C36 -175.5(5) . . . . ?
C35 C36 C41 N10 -49.8(7) . . . . ?
C39 C36 C41 N10 69.1(7) . . . . ?
C37 C36 C41 N10 -168.7(5) . . . . ?
C35 C36 C41 C42 136.0(7) . . . . ?
C39 C36 C41 C42 -105.1(7) . . . . ?
C37 C36 C41 C42 17.1(9) . . . . ?
N10 C41 C42 C43 -0.1(7) . . . . ?
C36 C41 C42 C43 174.8(6) . . . . ?
C41 C42 C43 C44 0.2(8) . . . . ?
C42 C43 C44 N11 177.8(6) . . . . ?
C42 C43 C44 N10 -0.3(8) . . . . ?
N12 N11 C44 C43 -170.7(7) . . . . ?
N12 N11 C44 N10 7.1(9) . . . . ?
C41 N10 C44 C43 0.2(7) . . . . ?
C41 N10 C44 N11 -177.9(6) . . . . ?
N11 N12 C45 C46 177.3(6) . . . . ?
N11 N12 C45 C50 -5.5(10) . . . . ?
C50 C45 C46 C47 -1.2(12) . . . . ?
N12 C45 C46 C47 176.2(7) . . . . ?
C45 C46 C47 C48 0.0(13) . . . . ?
C46 C47 C48 C49 1.1(14) . . . . ?
C46 C47 C48 Br4 179.6(7) . . . . ?
C47 C48 C49 C50 -1.0(14) . . . . ?
Br4 C48 C49 C50 -179.5(7) . . . . ?
C48 C49 C50 C45 -0.2(13) . . . . ?
C46 C45 C50 C49 1.3(12) . . . . ?
N12 C45 C50 C49 -175.8(7) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653611
