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#$Date: 2022-06-30 12:37:23 +0300 (Thu, 30 Jun 2022) $
#$Revision: 276449 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/55/8105594.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_8105594
loop_
_publ_author_name
'Fanfan, Shen'
'Shaomin, Xue'
'Jianlong, Wang'
_publ_section_title
;
 The crystal structure of 1,2-dimethyl-3,4-dinitrobenzene, C8H8N2O4
;
_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-2018-0248
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C8 H8 N2 O4'
_chemical_formula_sum            'C8 H8 N2 O4'
_chemical_formula_weight         196.16
_chemical_name_systematic
;
1,2-dimethyl-3,4-dinitrobenzene
;
_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
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 99.124(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.8936(7)
_cell_length_b                   14.4210(13)
_cell_length_c                   16.0109(15)
_cell_measurement_reflns_used    1935
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      23.52
_cell_measurement_theta_min      3.11
_cell_volume                     1799.5(3)
_computing_cell_refinement       'Bruker SMART[5]'
_computing_data_collection       'Bruker SMART[5]'
_computing_data_reduction        'Bruker SAINT[6]'
_computing_molecular_graphics    'Bruker SHELXTL[7]'
_computing_publication_material  'Bruker SHELXTL[7]'
_computing_structure_refinement  'Bruker SHELXTL[7]'
_computing_structure_solution    'Bruker SHELXTL[7]'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector[4]'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1020
_diffrn_reflns_av_unetI/netI     0.0792
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13096
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.419
_diffrn_reflns_theta_min         2.971
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;SADABS (Bruker, 2014) 
(Sheldrick, G. M. SADABS, version 2014/4. Bruker AXC Inc., Madison, WI, 2014)
;
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_description       column
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details ' '
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         3282
_refine_ls_number_restraints     87
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.1353
_refine_ls_R_factor_gt           0.0590
_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)+(0.0261P)²+1.6439P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1293
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1811
_reflns_number_total             3282
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0248_suppl.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8105594
_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   0.965
_shelx_estimated_absorpt_t_max   0.987
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
C1A C 1.1441(3) 0.3081(2) 0.23964(19) 0.0308(7) Uani 1 1 d . . . . .
C2A C 1.1138(3) 0.34172(19) 0.15757(19) 0.0279(7) Uani 1 1 d . . . . .
C3A C 1.0610(4) 0.2851(2) 0.08892(19) 0.0345(8) Uani 1 1 d . . . . .
C4A C 1.0335(4) 0.1907(2) 0.1050(2) 0.0384(8) Uani 1 1 d . . . . .
C5A C 1.0639(4) 0.1583(2) 0.1869(2) 0.0394(8) Uani 1 1 d . . . . .
H5A H 1.0462 0.0944 0.1971 0.047 Uiso 1 1 calc R U . . .
C6A C 1.1191(4) 0.2154(2) 0.2543(2) 0.0369(8) Uani 1 1 d . . . . .
H6A H 1.1397 0.1913 0.3102 0.044 Uiso 1 1 calc R U . . .
C7A C 1.0347(5) 0.3228(2) 0.0003(2) 0.0528(10) Uani 1 1 d . . . . .
H7A1 H 0.9127 0.3197 -0.0236 0.079 Uiso 1 1 calc R U . . .
H7A2 H 1.1010 0.2858 -0.0344 0.079 Uiso 1 1 calc R U . . .
H7A3 H 1.0734 0.3874 0.0013 0.079 Uiso 1 1 calc R U . . .
C8A C 0.9743(5) 0.1239(3) 0.0340(2) 0.0621(11) Uani 1 1 d . . . . .
H8A1 H 0.9560 0.0626 0.0575 0.093 Uiso 1 1 calc R U . . .
H8A2 H 1.0619 0.1194 -0.0029 0.093 Uiso 1 1 calc R U . . .
H8A3 H 0.8666 0.1462 0.0012 0.093 Uiso 1 1 calc R U . . .
C1B C 0.6326(4) 0.3808(2) 0.1312(2) 0.0371(8) Uani 1 1 d D . . . .
C2B C 0.6367(3) 0.3193(2) 0.1971(2) 0.0337(8) Uani 1 1 d . . . . .
C3B C 0.5990(4) 0.2261(2) 0.1842(2) 0.0411(8) Uani 1 1 d . . . . .
C4B C 0.5524(4) 0.1962(2) 0.1005(2) 0.0480(10) Uani 1 1 d . . . . .
C5B C 0.5519(4) 0.2595(3) 0.0352(2) 0.0546(10) Uani 1 1 d . . . . .
H5B H 0.5239 0.2385 -0.0216 0.066 Uiso 1 1 calc R U . . .
C6B C 0.5906(4) 0.3512(3) 0.0499(2) 0.0499(9) Uani 1 1 d . . . . .
H6B H 0.5882 0.3934 0.0041 0.060 Uiso 1 1 calc R U . . .
C7B C 0.6082(5) 0.1599(3) 0.2572(3) 0.0715(13) Uani 1 1 d . . . . .
H7B1 H 0.6787 0.1869 0.3071 0.107 Uiso 1 1 calc R U . . .
H7B2 H 0.6595 0.1014 0.2426 0.107 Uiso 1 1 calc R U . . .
H7B3 H 0.4923 0.1482 0.2694 0.107 Uiso 1 1 calc R U . . .
C8B C 0.5037(5) 0.0964(2) 0.0805(3) 0.0870(16) Uani 1 1 d . . . . .
H8B1 H 0.4676 0.0894 0.0194 0.131 Uiso 1 1 calc R U . . .
H8B2 H 0.4091 0.0787 0.1102 0.131 Uiso 1 1 calc R U . . .
H8B3 H 0.6028 0.0564 0.0991 0.131 Uiso 1 1 calc R U . . .
N1A N 1.1908(3) 0.3688(2) 0.31266(18) 0.0406(7) Uani 1 1 d . . . . .
N2A N 1.1402(3) 0.44083(17) 0.13973(17) 0.0379(7) Uani 1 1 d . . . . .
N2B N 0.6776(4) 0.3490(2) 0.28623(19) 0.0546(8) Uani 1 1 d . . . . .
O1A O 1.2353(3) 0.33283(18) 0.38171(15) 0.0578(7) Uani 1 1 d . . . . .
O2A O 1.1809(3) 0.45230(17) 0.30191(16) 0.0609(7) Uani 1 1 d . . . . .
O3A O 1.2848(3) 0.46599(15) 0.13367(16) 0.0557(7) Uani 1 1 d . . . . .
O4A O 1.0147(3) 0.49054(15) 0.12921(18) 0.0610(8) Uani 1 1 d . . . . .
O3B O 0.5581(3) 0.3687(2) 0.32266(17) 0.0725(9) Uani 1 1 d . . . . .
O4B O 0.8267(3) 0.3480(3) 0.31930(18) 0.1039(13) Uani 1 1 d . . . . .
N1B N 0.6641(8) 0.4803(3) 0.1517(5) 0.0497(14) Uani 0.83(2) 1 d D U P A 1
O1B O 0.6499(7) 0.5347(3) 0.0921(6) 0.0639(19) Uani 0.83(2) 1 d D U P A 1
O2B O 0.7031(10) 0.5029(5) 0.2252(5) 0.078(2) Uani 0.83(2) 1 d D U P A 1
N1Y N 0.662(3) 0.4820(11) 0.1213(19) 0.056(6) Uani 0.17(2) 1 d D U P A 2
O1Y O 0.680(4) 0.511(2) 0.052(2) 0.066(7) Uani 0.17(2) 1 d D U P A 2
O2Y O 0.668(4) 0.5262(15) 0.187(3) 0.064(6) Uani 0.17(2) 1 d D U P A 2
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'
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 119.6(3) . .
C6A C1A N1A 118.1(3) . .
C2A C1A N1A 122.2(3) . .
C3A C2A C1A 122.3(3) . .
C3A C2A N2A 116.9(3) . .
C1A C2A N2A 120.9(3) . .
C2A C3A C4A 117.5(3) . .
C2A C3A C7A 121.2(3) . .
C4A C3A C7A 121.3(3) . .
C5A C4A C3A 119.6(3) . .
C5A C4A C8A 119.2(3) . .
C3A C4A C8A 121.3(3) . .
C6A C5A C4A 122.0(3) . .
C6A C5A H5A 119.0 . .
C4A C5A H5A 119.0 . .
C5A C6A C1A 119.0(3) . .
C5A C6A H6A 120.5 . .
C1A C6A H6A 120.5 . .
C3A C7A H7A1 109.5 . .
C3A C7A H7A2 109.5 . .
H7A1 C7A H7A2 109.5 . .
C3A C7A H7A3 109.5 . .
H7A1 C7A H7A3 109.5 . .
H7A2 C7A H7A3 109.5 . .
C4A C8A H8A1 109.5 . .
C4A C8A H8A2 109.5 . .
H8A1 C8A H8A2 109.5 . .
C4A C8A H8A3 109.5 . .
H8A1 C8A H8A3 109.5 . .
H8A2 C8A H8A3 109.5 . .
C6B C1B C2B 120.3(3) . .
C6B C1B N1B 121.5(4) . .
C2B C1B N1B 118.1(4) . .
C6B C1B N1Y 103.0(12) . .
C2B C1B N1Y 136.7(12) . .
C1B C2B C3B 122.2(3) . .
C1B C2B N2B 122.0(3) . .
C3B C2B N2B 115.8(3) . .
C2B C3B C4B 117.4(3) . .
C2B C3B C7B 121.2(3) . .
C4B C3B C7B 121.4(3) . .
C5B C4B C3B 119.2(3) . .
C5B C4B C8B 119.8(4) . .
C3B C4B C8B 121.0(4) . .
C6B C5B C4B 122.1(3) . .
C6B C5B H5B 118.9 . .
C4B C5B H5B 118.9 . .
C1B C6B C5B 118.8(3) . .
C1B C6B H6B 120.6 . .
C5B C6B H6B 120.6 . .
C3B C7B H7B1 109.5 . .
C3B C7B H7B2 109.5 . .
H7B1 C7B H7B2 109.5 . .
C3B C7B H7B3 109.5 . .
H7B1 C7B H7B3 109.5 . .
H7B2 C7B H7B3 109.5 . .
C4B C8B H8B1 109.5 . .
C4B C8B H8B2 109.5 . .
H8B1 C8B H8B2 109.5 . .
C4B C8B H8B3 109.5 . .
H8B1 C8B H8B3 109.5 . .
H8B2 C8B H8B3 109.5 . .
O2A N1A O1A 123.4(3) . .
O2A N1A C1A 118.5(3) . .
O1A N1A C1A 118.0(3) . .
O4A N2A O3A 124.7(3) . .
O4A N2A C2A 117.4(2) . .
O3A N2A C2A 117.8(3) . .
O4B N2B O3B 124.5(3) . .
O4B N2B C2B 117.9(3) . .
O3B N2B C2B 117.6(3) . .
O2B N1B O1B 124.1(5) . .
O2B N1B C1B 118.8(5) . .
O1B N1B C1B 117.0(5) . .
O1Y N1Y O2Y 127.6(18) . .
O1Y N1Y C1B 118.6(14) . .
O2Y N1Y C1B 113.8(13) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1A C6A 1.377(4) .
C1A C2A 1.385(4) .
C1A N1A 1.460(4) .
C2A C3A 1.379(4) .
C2A N2A 1.479(4) .
C3A C4A 1.409(4) .
C3A C7A 1.502(4) .
C4A C5A 1.378(4) .
C4A C8A 1.507(4) .
C5A C6A 1.372(4) .
C5A H5A 0.9500 .
C6A H6A 0.9500 .
C7A H7A1 0.9800 .
C7A H7A2 0.9800 .
C7A H7A3 0.9800 .
C8A H8A1 0.9800 .
C8A H8A2 0.9800 .
C8A H8A3 0.9800 .
C1B C6B 1.360(5) .
C1B C2B 1.376(4) .
C1B N1B 1.485(5) .
C1B N1Y 1.491(16) .
C2B C3B 1.384(4) .
C2B N2B 1.476(4) .
C3B C4B 1.401(5) .
C3B C7B 1.502(5) .
C4B C5B 1.388(5) .
C4B C8B 1.510(4) .
C5B C6B 1.370(5) .
C5B H5B 0.9500 .
C6B H6B 0.9500 .
C7B H7B1 0.9800 .
C7B H7B2 0.9800 .
C7B H7B3 0.9800 .
C8B H8B1 0.9800 .
C8B H8B2 0.9800 .
C8B H8B3 0.9800 .
N1A O2A 1.217(3) .
N1A O1A 1.221(3) .
N2A O4A 1.213(3) .
N2A O3A 1.216(3) .
N2B O4B 1.212(3) .
N2B O3B 1.219(3) .
N1B O2B 1.212(6) .
N1B O1B 1.227(6) .
N1Y O1Y 1.215(14) .
N1Y O2Y 1.224(14) .
