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#$Date: 2022-05-11 12:31:14 +0300 (Wed, 11 May 2022) $
#$Revision: 275338 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/52/8105225.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_8105225
loop_
_publ_author_name
'Cai, Cao'
'Jingqi, Wang'
'Min, Li'
'Jun, Chen'
'Jianlong, Wang'
_publ_section_title
;
 The crystal structure of
 2-(4-chloro-6-nitrophenyl)-1-(4-chloro-3-nitrophenyl)diazene 1-oxide,
 C12H6Cl2N4O5
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              583
_journal_page_last               584
_journal_paper_doi               10.1515/ncrs-2019-0832
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C12 H6 Cl2 N4 O5'
_chemical_formula_sum            'C12 H6 Cl2 N4 O5'
_chemical_formula_weight         357.11
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 91.738(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4268(16)
_cell_length_b                   5.1250(8)
_cell_length_c                   23.569(4)
_cell_measurement_reflns_used    2907
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.143
_cell_measurement_theta_min      2.522
_cell_volume                     1379.6(4)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0834
_diffrn_reflns_av_unetI/netI     0.0748
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            13102
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.559
_diffrn_reflns_theta_min         2.446
_exptl_absorpt_coefficient_mu    0.504
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5260
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1667 before and 0.0691 after correction. The Ratio of minimum to maximum transmission is 0.7055. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.719
_exptl_crystal_description       needle
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.799
_refine_diff_density_min         -0.547
_refine_diff_density_rms         0.107
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3160
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0995
_refine_ls_R_factor_gt           0.0555
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0623P)²+2.1806P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1292
_refine_ls_wR_factor_ref         0.1632
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2159
_reflns_number_total             3160
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0832_suppl.cif
_cod_data_source_block           1
_cod_database_code               8105225
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.961
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C8(H8), C9(H9), C11(H11)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_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
Cl1 Cl 0.75384(8) 1.37305(18) 0.60943(4) 0.0272(2) Uani 1 1 d . . . . .
Cl2 Cl -0.07410(8) -0.18693(19) 0.65590(4) 0.0295(3) Uani 1 1 d . . . . .
O1 O 0.4785(2) 1.4111(5) 0.71470(11) 0.0320(6) Uani 1 1 d . . . . .
O2 O 0.6646(2) 1.3235(6) 0.72567(12) 0.0413(8) Uani 1 1 d . . . . .
O3 O 0.3692(2) 0.4381(5) 0.55879(10) 0.0246(6) Uani 1 1 d . . . . .
O4 O 0.1593(2) 0.7025(5) 0.52866(10) 0.0252(6) Uani 1 1 d . . . . .
O5 O 0.1094(2) 0.3319(5) 0.48992(10) 0.0262(6) Uani 1 1 d . . . . .
N1 N 0.5692(3) 1.3053(6) 0.70027(12) 0.0258(7) Uani 1 1 d . . . . .
N2 N 0.3636(2) 0.6114(6) 0.59636(12) 0.0197(6) Uani 1 1 d . . . . .
N3 N 0.2841(2) 0.6385(6) 0.63281(12) 0.0218(6) Uani 1 1 d . . . . .
N4 N 0.1341(2) 0.4705(6) 0.53126(11) 0.0207(6) Uani 1 1 d . . . . .
C1 C 0.5604(3) 1.1362(7) 0.65026(14) 0.0209(7) Uani 1 1 d . . . . .
C2 C 0.6427(3) 1.1484(7) 0.60794(15) 0.0218(7) Uani 1 1 d . . . . .
C3 C 0.6304(3) 0.9843(7) 0.56169(15) 0.0238(8) Uani 1 1 d . . . . .
H3 H 0.685123 0.992964 0.532181 0.029 Uiso 1 1 calc R . . . .
C4 C 0.5390(3) 0.8071(7) 0.55801(15) 0.0213(7) Uani 1 1 d . . . . .
H4 H 0.531694 0.690815 0.526708 0.026 Uiso 1 1 calc R . . . .
C5 C 0.4583(3) 0.8021(7) 0.60070(14) 0.0187(7) Uani 1 1 d . . . . .
C6 C 0.4666(3) 0.9659(7) 0.64676(14) 0.0203(7) Uani 1 1 d . . . . .
H6 H 0.409781 0.962321 0.675330 0.024 Uiso 1 1 calc R . . . .
C7 C 0.1974(3) 0.4385(7) 0.63311(14) 0.0206(7) Uani 1 1 d . . . . .
C8 C 0.1782(3) 0.3328(8) 0.68652(15) 0.0269(8) Uani 1 1 d . . . . .
H8 H 0.221852 0.396386 0.718569 0.032 Uiso 1 1 calc R . . . .
C9 C 0.0972(3) 0.1378(8) 0.69359(15) 0.0272(8) Uani 1 1 d . . . . .
H9 H 0.087130 0.061977 0.729896 0.033 Uiso 1 1 calc R . . . .
C10 C 0.0301(3) 0.0531(7) 0.64692(15) 0.0226(8) Uani 1 1 d . . . . .
C11 C 0.0443(3) 0.1577(7) 0.59385(14) 0.0211(7) Uani 1 1 d . . . . .
H11 H -0.002026 0.098765 0.562250 0.025 Uiso 1 1 calc R . . . .
C12 C 0.1278(3) 0.3508(7) 0.58743(14) 0.0187(7) 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O1 N1 O2 125.1(3) . .
O1 N1 C1 116.5(3) . .
O2 N1 C1 118.3(3) . .
O3 N2 N3 127.1(3) . .
O3 N2 C5 118.0(3) . .
N3 N2 C5 114.9(3) . .
N2 N3 C7 115.7(3) . .
O4 N4 O5 124.7(3) . .
O4 N4 C12 118.1(3) . .
O5 N4 C12 117.2(3) . .
C2 C1 N1 121.2(3) . .
C6 C1 N1 117.1(3) . .
C6 C1 C2 121.6(3) . .
C1 C2 Cl1 122.1(3) . .
C3 C2 Cl1 118.9(3) . .
C3 C2 C1 118.9(3) . .
C2 C3 H3 119.8 . .
C2 C3 C4 120.5(3) . .
C4 C3 H3 119.8 . .
C3 C4 H4 120.5 . .
C3 C4 C5 119.0(3) . .
C5 C4 H4 120.5 . .
C4 C5 N2 118.0(3) . .
C6 C5 N2 119.9(3) . .
C6 C5 C4 122.0(3) . .
C1 C6 H6 121.0 . .
C5 C6 C1 117.9(3) . .
C5 C6 H6 121.0 . .
C8 C7 N3 114.3(3) . .
C12 C7 N3 127.5(3) . .
C12 C7 C8 118.1(3) . .
C7 C8 H8 119.5 . .
C9 C8 C7 121.1(3) . .
C9 C8 H8 119.5 . .
C8 C9 H9 120.4 . .
C8 C9 C10 119.2(3) . .
C10 C9 H9 120.4 . .
C9 C10 Cl2 119.3(3) . .
C11 C10 Cl2 119.3(3) . .
C11 C10 C9 121.3(3) . .
C10 C11 H11 120.7 . .
C10 C11 C12 118.6(3) . .
C12 C11 H11 120.7 . .
C7 C12 N4 121.4(3) . .
C11 C12 N4 116.8(3) . .
C11 C12 C7 121.6(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C2 1.714(4) .
Cl2 C10 1.730(4) .
O1 N1 1.227(4) .
O2 N1 1.232(4) .
O3 N2 1.257(4) .
O4 N4 1.226(4) .
O5 N4 1.232(4) .
N1 C1 1.464(4) .
N2 N3 1.277(4) .
N2 C5 1.459(4) .
N3 C7 1.426(4) .
N4 C12 1.463(4) .
C1 C2 1.393(5) .
C1 C6 1.382(5) .
C2 C3 1.380(5) .
C3 H3 0.9500 .
C3 C4 1.385(5) .
C4 H4 0.9500 .
C4 C5 1.386(5) .
C5 C6 1.373(5) .
C6 H6 0.9500 .
C7 C8 1.394(5) .
C7 C12 1.393(4) .
C8 H8 0.9500 .
C8 C9 1.376(5) .
C9 H9 0.9500 .
C9 C10 1.391(5) .
C10 C11 1.375(5) .
C11 H11 0.9500 .
C11 C12 1.386(5) .
