#------------------------------------------------------------------------------
#$Date: 2023-01-17 12:23:28 +0200 (Tue, 17 Jan 2023) $
#$Revision: 280382 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/64/8106487.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_8106487
loop_
_publ_author_name
'Jianlong, Wang'
'Tianbei, Zhang'
'Lizhen, Chen'
_publ_section_title
;
 The crystal structure of 4-chloro-3,5-dinitroaniline, C6H4ClN3O4
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              215
_journal_page_last               216
_journal_paper_doi               10.1515/ncrs-2016-0210
_journal_volume                  232
_journal_year                    2017
_chemical_formula_moiety         'C6 H4 Cl N3 O4'
_chemical_formula_sum            'C6 H4 Cl N3 O4'
_chemical_formula_weight         217.57
_chemical_melting_point          481.2
_chemical_name_common            4-chloro-3,5-dinitroaniline
_chemical_name_systematic
;
4-chloro-3,5-dinitroaniline 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'Olex2 1.1'
_cell_angle_alpha                90.00
_cell_angle_beta                 115.472(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.1945(7)
_cell_length_b                   8.1107(3)
_cell_length_c                   15.3834(6)
_cell_measurement_reflns_used    3434
_cell_measurement_temperature    105.6
_cell_measurement_theta_max      29.1255
_cell_measurement_theta_min      2.9671
_cell_volume                     1598.90(14)
_computing_cell_refinement       CrysAlisPro
_computing_data_collection       CrysAlisPro
_computing_data_reduction        CrysAlisPro
_computing_molecular_graphics    OLEX2
_computing_publication_material  OLEX2
_computing_structure_refinement  SHELXL-97
_computing_structure_solution    SHELXS-2007
_diffrn_ambient_temperature      105.6
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6746
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.97
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.469
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84919
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'brownish red'
_exptl_crystal_density_diffrn    1.808
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         2817
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0269
_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)+(0.0361P)²+0.6448P] 
where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0664
_refine_ls_wR_factor_ref         0.0669
_reflns_number_gt                2743
_reflns_number_total             2817
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2016-0210_suppl.cif
_cod_data_source_block           exp_01
_cod_original_cell_volume        1598.90(12)
_cod_database_code               8106487
_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.
;
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 'x, -y, z+1/2'
3 'x+1/2, y+1/2, z'
4 '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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.27657(4) -0.20277(6) -0.21736(4) 0.01674(14) Uani 1 1 d . . .
O5 O -0.31206(14) -0.3147(2) 0.03255(12) 0.0200(4) Uani 1 1 d . . .
O3 O -0.08117(14) -0.2233(2) -0.24315(12) 0.0188(4) Uani 1 1 d . . .
O4 O -0.31047(15) -0.1024(2) -0.05187(14) 0.0229(4) Uani 1 1 d . . .
O1 O -0.04694(14) -0.4856(2) -0.22877(12) 0.0207(4) Uani 1 1 d . . .
N1 N -0.07356(15) -0.3566(2) -0.20375(13) 0.0143(4) Uani 1 1 d . . .
N3 N 0.04874(16) -0.5335(3) 0.12546(13) 0.0197(5) Uani 1 1 d . . .
H3A H 0.1034 -0.5726 0.1221 0.024 Uiso 1 1 calc R . .
H3B H 0.0422 -0.5405 0.1784 0.024 Uiso 1 1 calc R . .
N2 N -0.27819(15) -0.2369(2) -0.01607(13) 0.0142(4) Uani 1 1 d . . .
C3 C -0.01844(19) -0.4478(3) -0.04011(15) 0.0134(5) Uani 1 1 d . . .
H3 H 0.0381 -0.4959 -0.0458 0.016 Uiso 1 1 calc R . .
C2 C -0.09293(18) -0.3644(3) -0.11685(15) 0.0119(5) Uani 1 1 d . . .
C4 C -0.02805(18) -0.4600(3) 0.04634(15) 0.0131(5) Uani 1 1 d . . .
C1 C -0.18116(19) -0.2901(3) -0.11618(16) 0.0120(5) Uani 1 1 d . . .
C6 C -0.18946(19) -0.3083(3) -0.02876(16) 0.0122(5) Uani 1 1 d . . .
C5 C -0.11649(18) -0.3898(3) 0.04997(15) 0.0133(5) Uani 1 1 d . . .
H5 H -0.1260 -0.3984 0.1060 0.016 Uiso 1 1 calc R . .
Cl2 Cl -0.27376(4) -0.67217(6) -0.23098(4) 0.01614(13) Uani 1 1 d . . .
O6 O -0.00013(15) -0.8617(2) -0.22916(12) 0.0220(4) Uani 1 1 d . . .
O9 O -0.25860(15) -0.6992(2) 0.05115(12) 0.0251(4) Uani 1 1 d . . .
O8 O -0.36188(14) -0.7317(2) -0.09930(13) 0.0245(4) Uani 1 1 d . . .
O7 O -0.16757(15) -0.8849(2) -0.31063(11) 0.0209(4) Uani 1 1 d . . .
N6 N 0.05061(16) -1.0357(2) 0.09724(13) 0.0167(4) Uani 1 1 d . . .
H6A H 0.1020 -1.0804 0.0905 0.020 Uiso 1 1 calc R . .
H6B H 0.0475 -1.0406 0.1518 0.020 Uiso 1 1 calc R . .
N5 N -0.27561(16) -0.7382(2) -0.03103(14) 0.0165(4) Uani 1 1 d . . .
N4 N -0.08922(17) -0.8693(2) -0.23525(14) 0.0159(4) Uani 1 1 d . . .
C7 C -0.18559(18) -0.7890(3) -0.13825(16) 0.0120(5) Uani 1 1 d . . .
C10 C -0.02612(18) -0.9566(3) 0.02117(16) 0.0124(5) Uani 1 1 d . . .
C12 C -0.18703(19) -0.8014(3) -0.04777(17) 0.0127(5) Uani 1 1 d . . .
C9 C -0.02283(19) -0.9469(3) -0.06826(16) 0.0129(5) Uani 1 1 d . . .
H9 H 0.0318 -0.9958 -0.0768 0.016 Uiso 1 1 calc R . .
C8 C -0.10028(18) -0.8649(3) -0.14372(16) 0.0125(5) Uani 1 1 d . . .
C11 C -0.11030(19) -0.8806(3) 0.03037(16) 0.0135(5) Uani 1 1 d . . .
H11 H -0.1145 -0.8835 0.0890 0.016 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'
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
O3 N1 O1 124.9(2) . .
O3 N1 C2 118.42(19) . .
O1 N1 C2 116.66(19) . .
H3A N3 H3B 120.0 . .
C4 N3 H3A 120.0 . .
C4 N3 H3B 120.0 . .
O5 N2 C6 117.42(19) . .
O4 N2 O5 124.6(2) . .
O4 N2 C6 117.95(19) . .
C2 C3 H3 120.1 . .
C2 C3 C4 119.8(2) . .
C4 C3 H3 120.1 . .
C3 C2 N1 115.1(2) . .
C3 C2 C1 124.6(2) . .
C1 C2 N1 120.37(19) . .
N3 C4 C3 120.6(2) . .
N3 C4 C5 121.6(2) . .
C3 C4 C5 117.7(2) . .
C2 C1 Cl1 122.20(17) . .
C2 C1 C6 114.0(2) . .
C6 C1 Cl1 123.52(19) . .
C1 C6 N2 120.8(2) . .
C5 C6 N2 115.8(2) . .
C5 C6 C1 123.4(2) . .
C4 C5 H5 119.7 . .
C6 C5 C4 120.5(2) . .
C6 C5 H5 119.7 . .
H6A N6 H6B 120.0 . .
C10 N6 H6A 120.0 . .
C10 N6 H6B 120.0 . .
O9 N5 O8 123.8(2) . .
O9 N5 C12 117.7(2) . .
O8 N5 C12 118.49(19) . .
O6 N4 C8 116.88(19) . .
O7 N4 O6 124.42(19) . .
O7 N4 C8 118.66(19) . .
C12 C7 Cl2 123.06(18) . .
C8 C7 Cl2 122.30(17) . .
C8 C7 C12 114.3(2) . .
N6 C10 C9 121.1(2) . .
N6 C10 C11 121.2(2) . .
C9 C10 C11 117.6(2) . .
C7 C12 N5 121.6(2) . .
C11 C12 N5 114.8(2) . .
C11 C12 C7 123.5(2) . .
C10 C9 H9 119.9 . .
C8 C9 C10 120.2(2) . .
C8 C9 H9 119.9 . .
C7 C8 N4 121.2(2) . .
C9 C8 N4 114.6(2) . .
C9 C8 C7 124.2(2) . .
C10 C11 H11 119.9 . .
C12 C11 C10 120.1(2) . .
C12 C11 H11 119.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C1 1.716(2) .
O5 N2 1.224(2) .
O3 N1 1.221(3) .
O4 N2 1.219(3) .
O1 N1 1.229(3) .
N1 C2 1.477(3) .
N3 H3A 0.8600 .
N3 H3B 0.8600 .
N3 C4 1.373(3) .
N2 C6 1.474(3) .
C3 H3 0.9300 .
C3 C2 1.377(3) .
C3 C4 1.398(3) .
C2 C1 1.394(3) .
C4 C5 1.401(3) .
C1 C6 1.407(3) .
C6 C5 1.377(3) .
C5 H5 0.9300 .
Cl2 C7 1.721(2) .
O6 N4 1.229(3) .
O9 N5 1.222(3) .
O8 N5 1.224(3) .
O7 N4 1.220(3) .
N6 H6A 0.8600 .
N6 H6B 0.8600 .
N6 C10 1.368(3) .
N5 C12 1.480(3) .
N4 C8 1.483(3) .
C7 C12 1.404(3) .
C7 C8 1.393(3) .
C10 C9 1.399(3) .
C10 C11 1.405(3) .
C12 C11 1.385(3) .
C9 H9 0.9300 .
C9 C8 1.378(3) .
C11 H11 0.9300 .
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
Cl1 C1 C6 N2 -6.2(3) . . . .
Cl1 C1 C6 C5 174.80(17) . . . .
O5 N2 C6 C1 144.2(2) . . . .
O5 N2 C6 C5 -36.8(3) . . . .
O3 N1 C2 C3 -131.7(2) . . . .
O3 N1 C2 C1 48.0(3) . . . .
O4 N2 C6 C1 -38.2(3) . . . .
O4 N2 C6 C5 140.9(2) . . . .
O1 N1 C2 C3 45.6(3) . . . .
O1 N1 C2 C1 -134.6(2) . . . .
N1 C2 C1 Cl1 5.8(3) . . . .
N1 C2 C1 C6 179.72(19) . . . .
N3 C4 C5 C6 176.2(2) . . . .
N2 C6 C5 C4 -178.9(2) . . . .
C3 C2 C1 Cl1 -174.49(18) . . . .
C3 C2 C1 C6 -0.6(3) . . . .
C3 C4 C5 C6 -1.6(3) . . . .
C2 C3 C4 N3 -175.9(2) . . . .
C2 C3 C4 C5 2.0(3) . . . .
C2 C1 C6 N2 179.92(19) . . . .
C2 C1 C6 C5 1.0(3) . . . .
C4 C3 C2 N1 178.8(2) . . . .
C4 C3 C2 C1 -0.9(3) . . . .
C1 C6 C5 C4 0.1(3) . . . .
Cl2 C7 C12 N5 10.8(3) . . . .
Cl2 C7 C12 C11 -172.97(17) . . . .
Cl2 C7 C8 N4 -9.0(3) . . . .
Cl2 C7 C8 C9 173.89(18) . . . .
O6 N4 C8 C7 145.9(2) . . . .
O6 N4 C8 C9 -36.7(3) . . . .
O9 N5 C12 C7 -154.8(2) . . . .
O9 N5 C12 C11 28.7(3) . . . .
O8 N5 C12 C7 27.0(3) . . . .
O8 N5 C12 C11 -149.5(2) . . . .
O7 N4 C8 C7 -36.2(3) . . . .
O7 N4 C8 C9 141.2(2) . . . .
N6 C10 C9 C8 -179.2(2) . . . .
N6 C10 C11 C12 -180.0(2) . . . .
N5 C12 C11 C10 175.3(2) . . . .
C7 C12 C11 C10 -1.1(3) . . . .
C10 C9 C8 N4 -177.87(19) . . . .
C10 C9 C8 C7 -0.6(3) . . . .
C12 C7 C8 N4 177.42(19) . . . .
C12 C7 C8 C9 0.3(3) . . . .
C9 C10 C11 C12 0.8(3) . . . .
C8 C7 C12 N5 -175.63(19) . . . .
C8 C7 C12 C11 0.6(3) . . . .
C11 C10 C9 C8 0.0(3) . . . .
