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#$Date: 2022-09-20 12:32:28 +0300 (Tue, 20 Sep 2022) $
#$Revision: 278007 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/58/8105806.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_8105806
loop_
_publ_author_name
'Cao, Junyan'
'Wang, Jianlong'
'Li, Min'
'Zhang, Ke'
'Li, Shuai'
'Wan, Zhen'
_publ_section_title
;
 The crystal structure of
 2-(4-chloro-2,6-dinitrophenyl)-1-(4-chloro-3,5-dinitrophenyl)diazene
 1-oxide, C12H4Cl2N6O9
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              641
_journal_page_last               643
_journal_paper_doi               10.1515/ncrs-2018-0596
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C12 H4 Cl2 N6 O9'
_chemical_formula_sum            'C12 H4 Cl2 N6 O9'
_chemical_formula_weight         447.11
_chemical_name_systematic
;
2-(4-chloro-2,6-dinitrophenyl)-1-(4-chloro-3,5-dinitrophenyl)diazene 1-oxide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 91.927(2)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   50.136(3)
_cell_length_b                   8.1074(5)
_cell_length_c                   15.9816(11)
_cell_measurement_reflns_used    5048
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.28
_cell_measurement_theta_min      2.84
_cell_volume                     6492.4(7)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_av_unetI/netI     0.0546
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       60
_diffrn_reflns_limit_h_min       -51
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16784
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.361
_diffrn_reflns_theta_min         2.841
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.470
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
SADABS (Bruker, 2014)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.830
_exptl_crystal_description       block
_exptl_crystal_F_000             3584
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     523
_refine_ls_number_reflns         5924
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0427
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0424P)²+2.3063P]
 where P=(Fo²+2Fc²)/3'
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0849
_refine_ls_wR_factor_ref         0.0969
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4283
_reflns_number_total             5924
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0596_suppl.cif
_cod_data_source_block           exp_01
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               8105806
_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_min   0.900
_shelx_estimated_absorpt_t_max   0.937
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1A C 0.13861(5) 0.5902(3) 0.04922(16) 0.0163(6) Uani 1 1 d . . . . .
C2A C 0.14421(5) 0.5197(3) 0.12720(17) 0.0178(6) Uani 1 1 d . . . . .
C3A C 0.16927(5) 0.5303(3) 0.16593(17) 0.0173(6) Uani 1 1 d . . . . .
H3A H 0.1730 0.4790 0.2185 0.021 Uiso 1 1 calc R U . . .
C4A C 0.18864(5) 0.6174(3) 0.12609(16) 0.0157(6) Uani 1 1 d . . . . .
C5A C 0.18441(5) 0.6884(3) 0.04844(17) 0.0190(6) Uani 1 1 d . . . . .
H5A H 0.1981 0.7480 0.0219 0.023 Uiso 1 1 calc R U . . .
C6A C 0.15942(5) 0.6688(3) 0.01112(16) 0.0175(6) Uani 1 1 d . . . . .
C7A C 0.29165(5) 0.6196(3) 0.37139(17) 0.0182(6) Uani 1 1 d . . . . .
C8A C 0.29389(5) 0.6067(4) 0.28557(18) 0.0215(7) Uani 1 1 d . . . . .
H8A H 0.3108 0.6139 0.2607 0.026 Uiso 1 1 calc R U . . .
C9A C 0.27092(6) 0.5830(4) 0.23693(17) 0.0197(6) Uani 1 1 d . . . . .
C10A C 0.24547(5) 0.5781(3) 0.26960(16) 0.0158(6) Uani 1 1 d . . . . .
C11A C 0.24464(5) 0.5970(3) 0.35597(17) 0.0176(6) Uani 1 1 d . . . . .
C12A C 0.26713(5) 0.6145(3) 0.40753(17) 0.0192(6) Uani 1 1 d . . . . .
H12A H 0.2657 0.6229 0.4665 0.023 Uiso 1 1 calc R U . . .
C1B C 0.88857(5) -0.1256(3) 0.15552(17) 0.0173(6) Uani 1 1 d . . . . .
C2B C 0.90384(5) -0.0832(3) 0.08700(16) 0.0166(6) Uani 1 1 d . . . . .
C3B C 0.92360(5) 0.0350(3) 0.09233(16) 0.0161(6) Uani 1 1 d . . . . .
H3B H 0.9337 0.0617 0.0450 0.019 Uiso 1 1 calc R U . . .
C4B C 0.92837(5) 0.1132(3) 0.16758(17) 0.0157(6) Uani 1 1 d . . . . .
C5B C 0.91428(5) 0.0751(3) 0.23775(17) 0.0170(6) Uani 1 1 d . . . . .
H5B H 0.9181 0.1287 0.2897 0.020 Uiso 1 1 calc R U . . .
C6B C 0.89455(5) -0.0430(3) 0.23029(17) 0.0181(6) Uani 1 1 d . . . . .
C7B C 1.02603(5) 0.6043(3) 0.11146(16) 0.0168(6) Uani 1 1 d . . . . .
C8B C 1.00133(5) 0.6625(3) 0.13406(16) 0.0169(6) Uani 1 1 d . . . . .
H8B H 0.9990 0.7752 0.1483 0.020 Uiso 1 1 calc R U . . .
C9B C 0.98009(5) 0.5546(3) 0.13563(16) 0.0165(6) Uani 1 1 d . . . . .
C10B C 0.98240(5) 0.3874(3) 0.11764(16) 0.0170(6) Uani 1 1 d . . . . .
C11B C 1.00778(6) 0.3365(3) 0.09622(17) 0.0193(6) Uani 1 1 d . . . . .
C12B C 1.02947(5) 0.4402(3) 0.09115(16) 0.0186(6) Uani 1 1 d . . . . .
H12B H 1.0463 0.4000 0.0742 0.022 Uiso 1 1 calc R U . . .
Cl1A Cl 0.10813(2) 0.57844(9) -0.00203(5) 0.02560(18) Uani 1 1 d . . . . .
Cl2A Cl 0.32000(2) 0.64070(10) 0.43496(5) 0.0298(2) Uani 1 1 d . . . . .
Cl1B Cl 0.86541(2) -0.28033(10) 0.15009(5) 0.0308(2) Uani 1 1 d . . . . .
Cl2B Cl 1.05268(2) 0.73773(9) 0.10846(5) 0.02625(18) Uani 1 1 d . . . . .
N1A N 0.21515(4) 0.6396(3) 0.16596(14) 0.0174(5) Uani 1 1 d . . . . .
N2A N 0.22098(4) 0.5420(3) 0.22598(14) 0.0195(5) Uani 1 1 d . . . . .
N3A N 0.12375(5) 0.4306(3) 0.17325(15) 0.0297(6) Uani 1 1 d . . . . .
N4A N 0.15532(5) 0.7326(3) -0.07549(16) 0.0266(6) Uani 1 1 d . . . . .
N5A N 0.27425(5) 0.5568(3) 0.14686(15) 0.0272(6) Uani 1 1 d . . . . .
N6A N 0.21858(5) 0.6068(3) 0.39649(15) 0.0258(6) Uani 1 1 d . . . . .
N1B N 0.94919(4) 0.2392(3) 0.17577(14) 0.0178(5) Uani 1 1 d . . . . .
N2B N 0.96142(5) 0.2703(3) 0.10942(14) 0.0219(6) Uani 1 1 d . . . . .
N3B N 0.89958(5) -0.1634(3) 0.00462(14) 0.0196(5) Uani 1 1 d . . . . .
N4B N 0.87943(5) -0.0786(3) 0.30656(15) 0.0228(6) Uani 1 1 d . . . . .
N5B N 0.95392(5) 0.6286(3) 0.15257(15) 0.0222(6) Uani 1 1 d . . . . .
N6B N 1.01215(5) 0.1600(3) 0.08119(17) 0.0274(6) Uani 1 1 d . . . . .
O1A O 0.22933(4) 0.7533(2) 0.13873(13) 0.0261(5) Uani 1 1 d . . . . .
O2A O 0.10185(5) 0.4890(4) 0.17507(16) 0.0545(8) Uani 1 1 d . . . . .
O3A O 0.13100(5) 0.3029(3) 0.20785(14) 0.0417(6) Uani 1 1 d . . . . .
O4A O 0.16121(6) 0.6386(3) -0.13086(14) 0.0540(7) Uani 1 1 d . . . . .
O5A O 0.14760(6) 0.8704(4) -0.08457(16) 0.0598(8) Uani 1 1 d . . . . .
O6A O 0.29196(5) 0.6329(4) 0.11404(14) 0.0610(9) Uani 1 1 d . . . . .
O7A O 0.25941(4) 0.4593(3) 0.11086(12) 0.0308(5) Uani 1 1 d . . . . .
O8A O 0.20051(4) 0.6792(3) 0.35871(14) 0.0392(6) Uani 1 1 d . . . . .
O9A O 0.21735(4) 0.5486(3) 0.46613(14) 0.0425(6) Uani 1 1 d . . . . .
O1B O 0.95327(4) 0.3045(3) 0.24551(12) 0.0329(5) Uani 1 1 d . . . . .
O2B O 0.87693(4) -0.1948(3) -0.01900(13) 0.0300(5) Uani 1 1 d . . . . .
O3B O 0.91943(4) -0.1897(3) -0.03548(13) 0.0329(5) Uani 1 1 d . . . . .
O4B O 0.89251(4) -0.0934(3) 0.37174(13) 0.0344(5) Uani 1 1 d . . . . .
O5B O 0.85526(4) -0.0897(3) 0.29932(14) 0.0365(6) Uani 1 1 d . . . . .
O6B O 0.95376(4) 0.7545(3) 0.19408(13) 0.0323(5) Uani 1 1 d . . . . .
O7B O 0.93411(4) 0.5627(3) 0.12148(15) 0.0406(6) Uani 1 1 d . . . . .
O8B O 1.00398(5) 0.0643(3) 0.13355(16) 0.0459(6) Uani 1 1 d . . . . .
O9B O 1.02383(4) 0.1210(3) 0.01829(15) 0.0365(6) 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
C6A C1A C2A 116.9(2) . .
C6A C1A Cl1A 119.3(2) . .
C2A C1A Cl1A 123.8(2) . .
C3A C2A C1A 121.9(3) . .
C3A C2A N3A 116.4(2) . .
C1A C2A N3A 121.8(2) . .
C4A C3A C2A 118.0(2) . .
C4A C3A H3A 121.0 . .
C2A C3A H3A 121.0 . .
C3A C4A C5A 122.8(2) . .
C3A C4A N1A 120.4(2) . .
C5A C4A N1A 116.8(2) . .
C4A C5A C6A 116.9(3) . .
C4A C5A H5A 121.6 . .
C6A C5A H5A 121.6 . .
C5A C6A C1A 123.5(2) . .
C5A C6A N4A 117.3(2) . .
C1A C6A N4A 119.2(2) . .
C12A C7A C8A 121.1(2) . .
C12A C7A Cl2A 119.0(2) . .
C8A C7A Cl2A 119.9(2) . .
C9A C8A C7A 118.3(3) . .
C9A C8A H8A 120.8 . .
C7A C8A H8A 120.8 . .
C8A C9A C10A 123.3(3) . .
C8A C9A N5A 116.8(2) . .
C10A C9A N5A 119.8(2) . .
C11A C10A C9A 115.3(2) . .
C11A C10A N2A 117.1(2) . .
C9A C10A N2A 127.4(2) . .
C12A C11A C10A 123.5(2) . .
C12A C11A N6A 116.6(2) . .
C10A C11A N6A 119.8(2) . .
C7A C12A C11A 118.4(3) . .
C7A C12A H12A 120.8 . .
C11A C12A H12A 120.8 . .
C6B C1B C2B 116.4(2) . .
C6B C1B Cl1B 121.5(2) . .
C2B C1B Cl1B 121.9(2) . .
C3B C2B C1B 122.2(2) . .
C3B C2B N3B 116.3(2) . .
C1B C2B N3B 121.5(2) . .
C4B C3B C2B 118.6(3) . .
C4B C3B H3B 120.7 . .
C2B C3B H3B 120.7 . .
C3B C4B C5B 122.0(2) . .
C3B C4B N1B 120.2(2) . .
C5B C4B N1B 117.8(2) . .
C6B C5B C4B 118.1(2) . .
C6B C5B H5B 121.0 . .
C4B C5B H5B 121.0 . .
C5B C6B C1B 122.7(3) . .
C5B C6B N4B 116.7(2) . .
C1B C6B N4B 120.6(2) . .
C12B C7B C8B 120.6(3) . .
C12B C7B Cl2B 119.7(2) . .
C8B C7B Cl2B 119.7(2) . .
C9B C8B C7B 119.1(3) . .
C9B C8B H8B 120.4 . .
C7B C8B H8B 120.4 . .
C8B C9B C10B 123.0(3) . .
C8B C9B N5B 115.9(2) . .
C10B C9B N5B 121.0(2) . .
C11B C10B C9B 115.0(3) . .
C11B C10B N2B 117.4(3) . .
C9B C10B N2B 127.2(3) . .
C12B C11B C10B 124.3(3) . .
C12B C11B N6B 117.5(3) . .
C10B C11B N6B 118.1(3) . .
C11B C12B C7B 117.9(3) . .
C11B C12B H12B 121.0 . .
C7B C12B H12B 121.0 . .
O1A N1A N2A 127.0(2) . .
O1A N1A C4A 117.2(2) . .
N2A N1A C4A 115.7(2) . .
N1A N2A C10A 114.5(2) . .
O2A N3A O3A 125.6(3) . .
O2A N3A C2A 118.3(3) . .
O3A N3A C2A 116.1(2) . .
O5A N4A O4A 126.0(3) . .
O5A N4A C6A 118.3(3) . .
O4A N4A C6A 115.6(3) . .
O6A N5A O7A 124.8(3) . .
O6A N5A C9A 117.3(3) . .
O7A N5A C9A 118.0(2) . .
O9A N6A O8A 125.5(3) . .
O9A N6A C11A 117.0(2) . .
O8A N6A C11A 117.4(2) . .
O1B N1B N2B 126.5(2) . .
O1B N1B C4B 118.2(2) . .
N2B N1B C4B 115.3(2) . .
N1B N2B C10B 115.7(2) . .
O2B N3B O3B 124.9(2) . .
O2B N3B C2B 118.4(2) . .
O3B N3B C2B 116.7(2) . .
O5B N4B O4B 125.4(3) . .
O5B N4B C6B 118.1(2) . .
O4B N4B C6B 116.5(2) . .
O6B N5B O7B 124.7(3) . .
O6B N5B C9B 117.6(2) . .
O7B N5B C9B 117.6(2) . .
O8B N6B O9B 125.5(3) . .
O8B N6B C11B 116.8(3) . .
O9B N6B C11B 117.7(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1A C6A 1.381(4) .
C1A C2A 1.391(4) .
C1A Cl1A 1.712(3) .
C2A C3A 1.384(4) .
C2A N3A 1.472(4) .
C3A C4A 1.374(4) .
C3A H3A 0.9500 .
C4A C5A 1.378(4) .
C4A N1A 1.466(3) .
C5A C6A 1.379(4) .
C5A H5A 0.9500 .
C6A N4A 1.485(3) .
C7A C12A 1.376(4) .
C7A C8A 1.384(4) .
C7A Cl2A 1.727(3) .
C8A C9A 1.381(4) .
C8A H8A 0.9500 .
C9A C10A 1.395(4) .
C9A N5A 1.470(4) .
C10A C11A 1.391(4) .
C10A N2A 1.422(3) .
C11A C12A 1.381(4) .
C11A N6A 1.480(3) .
C12A H12A 0.9500 .
C1B C6B 1.394(4) .
C1B C2B 1.400(4) .
C1B Cl1B 1.709(3) .
C2B C3B 1.379(4) .
C2B N3B 1.477(3) .
C3B C4B 1.373(4) .
C3B H3B 0.9500 .
C4B C5B 1.380(4) .
C4B N1B 1.463(3) .
C5B C6B 1.378(4) .
C5B H5B 0.9500 .
C6B N4B 1.485(4) .
C7B C12B 1.382(4) .
C7B C8B 1.384(4) .
C7B Cl2B 1.721(3) .
C8B C9B 1.379(4) .
C8B H8B 0.9500 .
C9B C10B 1.392(4) .
C9B N5B 1.476(3) .
C10B C11B 1.391(4) .
C10B N2B 1.420(3) .
C11B C12B 1.379(4) .
C11B N6B 1.469(4) .
C12B H12B 0.9500 .
N1A O1A 1.251(3) .
N1A N2A 1.270(3) .
N3A O2A 1.197(3) .
N3A O3A 1.223(3) .
N4A O5A 1.190(3) .
N4A O4A 1.212(3) .
N5A O6A 1.215(3) .
N5A O7A 1.217(3) .
N6A O9A 1.213(3) .
N6A O8A 1.222(3) .
N1B O1B 1.245(3) .
N1B N2B 1.268(3) .
N3B O2B 1.212(3) .
N3B O3B 1.220(3) .
N4B O5B 1.217(3) .
N4B O4B 1.218(3) .
N5B O6B 1.217(3) .
N5B O7B 1.219(3) .
N6B O8B 1.221(3) .
N6B O9B 1.222(3) .
