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#$Date: 2022-12-06 11:36:56 +0200 (Tue, 06 Dec 2022) $
#$Revision: 279732 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/63/8106340.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_8106340
loop_
_publ_author_name
'Junyan, Cao'
'Jianlong, Wang'
'Lizhen, Chen'
'Luyao, Zhang'
_publ_section_title
;
 Crystal structure of
 2-(4-chloro-2,6-dinitrophenyl)-1-(4-chloro-3-nitrophenyl)diazene 1-oxide,
 C12H5Cl2N5O7
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              905
_journal_page_last               906
_journal_paper_doi               10.1515/ncrs-2018-0091
_journal_volume                  233
_journal_year                    2018
_chemical_formula_moiety
;
C12 H5 Cl2 N5 O7'
;
_chemical_formula_sum            'C12 H5 Cl2 N5 O7'
_chemical_formula_weight         402.11
_chemical_name_systematic
;
2-(4-chloro-2,6-dinitrophenyl)-1-(4-chloro-3-nitrophenyl)diazene oxide 
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                93.370(4)
_cell_angle_beta                 101.590(4)
_cell_angle_gamma                118.222(3)
_cell_formula_units_Z            2
_cell_length_a                   8.2425(8)
_cell_length_b                   8.2814(7)
_cell_length_c                   12.4713(12)
_cell_measurement_reflns_used    1557
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.28
_cell_measurement_theta_min      2.84
_cell_volume                     723.03(12)
_computing_cell_refinement       'APEX3 (Bruker, 2016)[6]'
_computing_data_collection       'APEX3 (Bruker, 2016)[6]'
_computing_data_reduction        'APEX3 (Bruker, 2016)[6]'
_computing_molecular_graphics    OLEX2[8]
_computing_publication_material  OLEX2[8]
_computing_structure_refinement  SHELXL-2014[7]
_computing_structure_solution    'APEX3 (Bruker, 2016)[6]'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0893
_diffrn_reflns_av_unetI/netI     0.0970
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7671
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.369
_diffrn_reflns_theta_min         2.837
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.504
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6601
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
SADABS (Bruker, 2014)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.847
_exptl_crystal_description       sheet
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2626
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.1078
_refine_ls_R_factor_gt           0.0516
_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)+(0.0262P)²+0.0260P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0738
_refine_ls_wR_factor_ref         0.0858
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1683
_reflns_number_total             2626
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0091_suppl.cif
_cod_data_source_block           exp_01
_cod_database_code               8106340
_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   0.910
_shelx_estimated_absorpt_t_max   0.975
loop_
_space_group_symop_operation_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_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
C1 C 0.7600(5) 0.7866(4) 0.4462(3) 0.0180(8) Uani 1 1 d . . . . .
C2 C 0.8634(5) 0.7049(4) 0.4969(3) 0.0160(8) Uani 1 1 d . . . . .
C3 C 0.8398(5) 0.6405(4) 0.5953(3) 0.0164(8) Uani 1 1 d . . . . .
H3 H 0.9139 0.5895 0.6306 0.020 Uiso 1 1 calc R U . . .
C4 C 0.7070(5) 0.6520(4) 0.6407(3) 0.0158(8) Uani 1 1 d . . . . .
C5 C 0.6029(5) 0.7315(4) 0.5938(3) 0.0184(8) Uani 1 1 d . . . . .
H5 H 0.5118 0.7381 0.6273 0.022 Uiso 1 1 calc R U . . .
C6 C 0.6325(5) 0.8017(4) 0.4974(3) 0.0201(8) Uani 1 1 d . . . . .
H6 H 0.5646 0.8609 0.4660 0.024 Uiso 1 1 calc R U . . .
C7 C 0.7299(4) 0.2928(4) 1.0799(3) 0.0165(8) Uani 1 1 d . . . . .
C8 C 0.7384(4) 0.4634(4) 1.0794(3) 0.0167(8) Uani 1 1 d . . . . .
H8 H 0.7338 0.5270 1.1437 0.020 Uiso 1 1 calc R U . . .
C9 C 0.7536(4) 0.5400(4) 0.9837(3) 0.0155(8) Uani 1 1 d . . . . .
C10 C 0.7560(4) 0.4492(4) 0.8861(3) 0.0159(8) Uani 1 1 d . . . . .
C11 C 0.7494(4) 0.2788(4) 0.8933(3) 0.0152(8) Uani 1 1 d . . . . .
C12 C 0.7385(4) 0.2004(4) 0.9877(3) 0.0162(8) Uani 1 1 d . . . . .
H12 H 0.7370 0.0851 0.9892 0.019 Uiso 1 1 calc R U . . .
Cl1 Cl 0.79370(13) 0.87469(11) 0.32644(7) 0.0256(3) Uani 1 1 d . . . . .
Cl2 Cl 0.70640(13) 0.19242(12) 1.19747(7) 0.0248(2) Uani 1 1 d . . . . .
N1 N 0.6725(4) 0.5764(3) 0.7422(2) 0.0168(7) Uani 1 1 d . . . . .
N2 N 0.7855(4) 0.5200(4) 0.7871(2) 0.0186(7) Uani 1 1 d . . . . .
N3 N 1.0025(4) 0.6857(4) 0.4484(2) 0.0212(7) Uani 1 1 d . . . . .
N4 N 0.7751(4) 0.7269(4) 0.9895(2) 0.0219(7) Uani 1 1 d . . . . .
N5 N 0.7539(4) 0.1743(4) 0.7954(2) 0.0202(7) Uani 1 1 d . . . . .
O1 O 0.5385(3) 0.5729(3) 0.77512(19) 0.0250(6) Uani 1 1 d . . . . .
O2 O 0.9566(4) 0.6263(3) 0.34839(19) 0.0299(6) Uani 1 1 d . . . . .
O3 O 1.1540(3) 0.7212(3) 0.51273(19) 0.0287(6) Uani 1 1 d . . . . .
O4 O 0.6984(4) 0.7694(3) 1.0515(2) 0.0314(7) Uani 1 1 d . . . . .
O5 O 0.8703(4) 0.8288(3) 0.93295(19) 0.0327(7) Uani 1 1 d . . . . .
O6 O 0.6406(3) 0.1458(3) 0.70681(19) 0.0301(7) Uani 1 1 d . . . . .
O7 O 0.8698(4) 0.1203(3) 0.8099(2) 0.0307(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'
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
C6 C1 C2 118.3(3) . .
C6 C1 Cl1 119.7(3) . .
C2 C1 Cl1 122.0(3) . .
C3 C2 C1 121.4(3) . .
C3 C2 N3 117.0(3) . .
C1 C2 N3 121.6(3) . .
C4 C3 C2 118.2(3) . .
C4 C3 H3 120.9 . .
C2 C3 H3 120.9 . .
C3 C4 C5 122.2(3) . .
C3 C4 N1 119.4(3) . .
C5 C4 N1 118.4(3) . .
C4 C5 C6 119.1(3) . .
C4 C5 H5 120.5 . .
C6 C5 H5 120.5 . .
C5 C6 C1 120.7(3) . .
C5 C6 H6 119.6 . .
C1 C6 H6 119.6 . .
C12 C7 C8 121.0(3) . .
C12 C7 Cl2 119.3(3) . .
C8 C7 Cl2 119.7(3) . .
C7 C8 C9 118.9(3) . .
C7 C8 H8 120.6 . .
C9 C8 H8 120.6 . .
C8 C9 C10 122.5(3) . .
C8 C9 N4 116.9(3) . .
C10 C9 N4 120.5(3) . .
C11 C10 C9 115.3(3) . .
C11 C10 N2 117.1(3) . .
C9 C10 N2 127.2(3) . .
C12 C11 C10 123.7(3) . .
C12 C11 N5 117.1(3) . .
C10 C11 N5 119.2(3) . .
C7 C12 C11 118.4(3) . .
C7 C12 H12 120.8 . .
C11 C12 H12 120.8 . .
O1 N1 N2 127.1(3) . .
O1 N1 C4 117.6(3) . .
N2 N1 C4 115.3(3) . .
N1 N2 C10 116.0(3) . .
O2 N3 O3 124.6(3) . .
O2 N3 C2 118.2(3) . .
O3 N3 C2 117.1(3) . .
O5 N4 O4 125.1(3) . .
O5 N4 C9 117.3(3) . .
O4 N4 C9 117.6(3) . .
O7 N5 O6 125.0(3) . .
O7 N5 C11 116.9(3) . .
O6 N5 C11 118.1(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.382(5) .
C1 C2 1.400(4) .
C1 Cl1 1.716(3) .
C2 C3 1.380(4) .
C2 N3 1.465(4) .
C3 C4 1.367(5) .
C3 H3 0.9500 .
C4 C5 1.375(5) .
C4 N1 1.464(4) .
C5 C6 1.382(4) .
C5 H5 0.9500 .
C6 H6 0.9500 .
C7 C12 1.376(5) .
C7 C8 1.381(4) .
C7 Cl2 1.728(3) .
C8 C9 1.385(4) .
C8 H8 0.9500 .
C9 C10 1.401(5) .
C9 N4 1.468(4) .
C10 C11 1.395(4) .
C10 N2 1.414(4) .
C11 C12 1.376(4) .
C11 N5 1.471(4) .
C12 H12 0.9500 .
N1 O1 1.241(4) .
N1 N2 1.278(4) .
N3 O2 1.226(3) .
N3 O3 1.229(3) .
N4 O5 1.221(3) .
N4 O4 1.224(4) .
N5 O7 1.221(3) .
N5 O6 1.223(3) .
