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#$Date: 2022-05-02 11:16:29 +0300 (Mon, 02 May 2022) $
#$Revision: 274785 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/50/8105095.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_8105095
loop_
_publ_author_name
'Mei, Xue'
'Yong, Xiang'
'Jian, Wang'
'Yushan, Zhang'
'Yuehua, Yao'
'Jianlong, Wang'
_publ_section_title
;
 The crystal structure of 3-chloro-1-hydrazino-2,4,6-trinitrobenzene,
 C6H4ClN5O6
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              317
_journal_page_last               318
_journal_paper_doi               10.1515/ncrs-2019-0647
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C6 H4 Cl N5 O6'
_chemical_formula_sum            'C6 H4 Cl N5 O6'
_chemical_formula_weight         277.59
_chemical_name_systematic
;
3-chloro-1-hydrazino-2,4,6-trinitrobenzene
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 106.484(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2139(13)
_cell_length_b                   5.6835(6)
_cell_length_c                   17.597(2)
_cell_measurement_reflns_used    1818
_cell_measurement_temperature    173
_cell_measurement_theta_max      25.024
_cell_measurement_theta_min      2.684
_cell_volume                     979.5(2)
_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      173
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0698
_diffrn_reflns_av_unetI/netI     0.0742
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7003
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.414
_exptl_absorpt_coefficient_mu    0.426
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6435
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker,2016/2)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.882
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         1974
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0958
_refine_ls_R_factor_gt           0.0497
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0379P)²+0.2908P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.1138
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1268
_reflns_number_total             1974
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0647_suppl.cif
_cod_data_source_block           22019736062101_0m
_cod_original_cell_volume        979.6(2)
_cod_database_code               8105095
_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   0.983
_shelx_estimated_absorpt_t_min   0.967
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
Cl1 Cl 0.61771(8) 0.79091(15) 0.50526(5) 0.0355(3) Uani 1 1 d . . . . .
O1 O 0.9015(2) 0.6515(5) 0.55432(14) 0.0455(7) Uani 1 1 d . . . . .
O2 O 0.9138(2) 0.2714(5) 0.56408(14) 0.0475(7) Uani 1 1 d . . . . .
O3 O 0.7745(2) -0.1102(4) 0.31743(15) 0.0432(7) Uani 1 1 d . . . . .
O4 O 0.5901(2) -0.0182(4) 0.22709(13) 0.0365(6) Uani 1 1 d . . . . .
O5 O 0.3144(2) 0.5900(4) 0.35412(14) 0.0421(7) Uani 1 1 d . . . . .
O6 O 0.4257(2) 0.9114(4) 0.34942(14) 0.0358(6) Uani 1 1 d . . . . .
N1 N 0.8632(3) 0.4537(5) 0.53113(16) 0.0335(7) Uani 1 1 d . . . . .
N2 N 0.6758(3) 0.0201(5) 0.29058(17) 0.0308(7) Uani 1 1 d . . . . .
N3 N 0.4650(3) 0.3801(5) 0.23775(15) 0.0309(7) Uani 1 1 d . . . . .
H3 H 0.459213 0.254406 0.207780 0.037 Uiso 1 1 calc R . . . .
N4 N 0.3823(3) 0.5769(5) 0.20935(18) 0.0349(7) Uani 1 1 d . . . . .
N5 N 0.4178(3) 0.6978(5) 0.35429(16) 0.0291(6) Uani 1 1 d . . . . .
C1 C 0.7524(3) 0.4303(5) 0.45836(18) 0.0253(7) Uani 1 1 d . . . . .
C2 C 0.7578(3) 0.2478(5) 0.40926(18) 0.0263(7) Uani 1 1 d . . . . .
H2 H 0.829735 0.136294 0.424932 0.032 Uiso 1 1 calc R . . . .
C3 C 0.6611(3) 0.2220(5) 0.33753(18) 0.0232(7) Uani 1 1 d . . . . .
C4 C 0.5519(3) 0.3844(5) 0.30993(18) 0.0237(7) Uani 1 1 d . . . . .
C5 C 0.5443(3) 0.5575(5) 0.36709(18) 0.0238(7) Uani 1 1 d . . . . .
C6 C 0.6411(3) 0.5870(5) 0.43848(18) 0.0250(7) Uani 1 1 d . . . . .
H4A H 0.303(3) 0.529(5) 0.1891(19) 0.027(9) Uiso 1 1 d . . . . .
H4B H 0.417(4) 0.658(7) 0.174(2) 0.063(13) Uiso 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 124.5(3) . .
O1 N1 C1 118.3(3) . .
O2 N1 C1 117.2(3) . .
O3 N2 C3 117.7(3) . .
O4 N2 O3 122.5(3) . .
O4 N2 C3 119.9(3) . .
N4 N3 H3 120.1 . .
C4 N3 H3 120.1 . .
C4 N3 N4 119.8(3) . .
N3 N4 H4A 108(2) . .
N3 N4 H4B 109(2) . .
H4A N4 H4B 113(3) . .
O5 N5 O6 125.0(3) . .
O5 N5 C5 116.6(3) . .
O6 N5 C5 118.3(3) . .
C2 C1 N1 117.8(3) . .
C2 C1 C6 120.0(3) . .
C6 C1 N1 122.2(3) . .
C1 C2 H2 119.4 . .
C1 C2 C3 121.1(3) . .
C3 C2 H2 119.4 . .
C2 C3 N2 116.5(3) . .
C2 C3 C4 122.3(3) . .
C4 C3 N2 121.2(3) . .
N3 C4 C3 124.1(3) . .
N3 C4 C5 122.2(3) . .
C3 C4 C5 113.7(3) . .
C4 C5 N5 119.0(3) . .
C6 C5 N5 116.5(3) . .
C6 C5 C4 124.2(3) . .
C1 C6 Cl1 121.1(2) . .
C5 C6 Cl1 120.4(2) . .
C5 C6 C1 118.2(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C6 1.715(3) .
O1 N1 1.222(3) .
O2 N1 1.228(3) .
O3 N2 1.232(3) .
O4 N2 1.227(3) .
O5 N5 1.220(3) .
O6 N5 1.221(3) .
N1 C1 1.455(4) .
N2 C3 1.446(4) .
N3 H3 0.8800 .
N3 N4 1.405(4) .
N3 C4 1.327(4) .
N4 H4A 0.83(3) .
N4 H4B 0.92(4) .
N5 C5 1.480(4) .
C1 C2 1.361(4) .
C1 C6 1.407(4) .
C2 H2 0.9500 .
C2 C3 1.372(4) .
C3 C4 1.423(4) .
C4 C5 1.425(4) .
C5 C6 1.371(4) .
