#------------------------------------------------------------------------------
#$Date: 2022-04-26 10:44:07 +0300 (Tue, 26 Apr 2022) $
#$Revision: 274676 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/50/8105062.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_8105062
loop_
_publ_author_name
'Yong, Wang'
'Jun, Yuan'
'Duanlin, Cao'
'Jianlong, Wang'
'Lizhen, Chen'
_publ_section_title
;
 The crystal structure of bis(4-nitroimidazole-1-1yl)methane, C7H6N6O4
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              217
_journal_page_last               218
_journal_paper_doi               10.1515/ncrs-2019-0582
_journal_volume                  235
_journal_year                    2019
_chemical_formula_moiety         'C7 H6 N6 O4'
_chemical_formula_sum            'C7 H6 N6 O4'
_chemical_formula_weight         238.18
_chemical_name_systematic        Bis(imidazole-1-yl)methane
_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'
_audit_creation_method           'Olex2 1.1 '
_cell_angle_alpha                90
_cell_angle_beta                 102.3790(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.0402(7)
_cell_length_b                   7.9959(3)
_cell_length_c                   11.8012(4)
_cell_measurement_reflns_used    8720
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.360
_cell_measurement_theta_min      2.733
_cell_volume                     1939.22(12)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 [9] '
_computing_publication_material  'Olex2 [9]'
_computing_structure_refinement  'SHELXL [7]'
_computing_structure_solution    'SHELX [8]'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17779
_diffrn_reflns_theta_full        26.242
_diffrn_reflns_theta_max         26.399
_diffrn_reflns_theta_min         2.733
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  0.2602
_exptl_absorpt_correction_T_min  0.2179
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   .
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.632
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_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     307
_refine_ls_number_reflns         3885
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0481
_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)+(0.0563P)²+1.2349P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1184
_refine_ls_wR_factor_ref         0.1296
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3131
_reflns_number_total             3885
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0582_suppl.cif
_cod_data_source_block           exp_6069
_cod_database_code               8105062
_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   0.989
_shelx_estimated_absorpt_t_min   0.978
_olex2_refinement_description
;

1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C12(H12), C1(H1), C9(H9), C14(H14), C10(H10), C3(H3), C7(H7)
;
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
O8 O 0.89684(8) -0.1999(2) 1.03517(14) 0.0473(4) Uani 1 1 d . . . . .
O4 O 0.28112(8) 0.8320(2) 0.77591(14) 0.0457(4) Uani 1 1 d . . . . .
O7 O 0.98989(8) -0.2980(2) 1.01603(15) 0.0494(4) Uani 1 1 d . . . . .
O3 O 0.37100(7) 0.8863(2) 0.72055(15) 0.0494(4) Uani 1 1 d . . . . .
N3 N 0.40881(8) 0.2963(2) 0.48938(14) 0.0323(4) Uani 1 1 d . . . . .
N11 N 0.99290(8) -0.0799(2) 0.83821(15) 0.0356(4) Uani 1 1 d . . . . .
N9 N 0.83789(8) 0.1188(2) 0.57747(15) 0.0351(4) Uani 1 1 d . . . . .
N10 N 0.91305(7) 0.0930(2) 0.75936(14) 0.0338(4) Uani 1 1 d . . . . .
N12 N 0.94339(8) -0.2031(2) 0.98760(15) 0.0365(4) Uani 1 1 d . . . . .
O2 O 0.59384(8) 0.0466(2) 0.64212(16) 0.0595(5) Uani 1 1 d . . . . .
O1 O 0.51996(9) 0.0045(2) 0.74135(15) 0.0593(5) Uani 1 1 d . . . . .
N6 N 0.32105(8) 0.8039(2) 0.71549(15) 0.0369(4) Uani 1 1 d . . . . .
N4 N 0.32062(8) 0.4694(2) 0.51962(15) 0.0349(4) Uani 1 1 d . . . . .
N8 N 0.76113(9) -0.0429(2) 0.47366(16) 0.0421(4) Uani 1 1 d . . . . .
O5 O 0.76985(11) -0.1984(2) 0.27015(16) 0.0682(6) Uani 1 1 d . . . . .
N2 N 0.51421(9) 0.2598(2) 0.49720(17) 0.0438(4) Uani 1 1 d . . . . .
O6 O 0.86232(11) -0.0747(3) 0.27101(17) 0.0706(6) Uani 1 1 d . . . . .
N1 N 0.53978(9) 0.0682(2) 0.66043(17) 0.0453(5) Uani 1 1 d . . . . .
N7 N 0.81427(11) -0.1034(3) 0.31257(17) 0.0515(5) Uani 1 1 d . . . . .
N5 N 0.25439(10) 0.5756(3) 0.6235(2) 0.0625(7) Uani 1 1 d . . . . .
C5 C 0.35072(9) 0.6089(3) 0.57166(17) 0.0340(4) Uani 1 1 d . . . . .
H5 H 0.391383 0.654483 0.564595 0.041 Uiso 1 1 calc R . . . .
C13 C 0.94201(9) -0.0905(2) 0.89307(17) 0.0319(4) Uani 1 1 d . . . . .
C2 C 0.49453(10) 0.1719(2) 0.58274(17) 0.0341(4) Uani 1 1 d . . . . .
C12 C 0.89224(9) 0.0136(3) 0.84660(18) 0.0346(4) Uani 1 1 d . . . . .
H12 H 0.852026 0.027650 0.869765 0.042 Uiso 1 1 calc R . . . .
C1 C 0.43008(10) 0.1908(3) 0.57943(18) 0.0369(5) Uani 1 1 d . . . . .
H1 H 0.405367 0.141241 0.629143 0.044 Uiso 1 1 calc R . . . .
C6 C 0.30935(9) 0.6676(2) 0.63575(18) 0.0339(4) Uani 1 1 d . . . . .
C8 C 0.81183(11) -0.0217(3) 0.42008(18) 0.0380(5) Uani 1 1 d . . . . .
C9 C 0.85972(10) 0.0763(3) 0.48104(18) 0.0386(5) Uani 1 1 d . . . . .
H9 H 0.899413 0.107965 0.460968 0.046 Uiso 1 1 calc R . . . .
C11 C 0.87474(10) 0.2089(3) 0.67704(19) 0.0394(5) Uani 1 1 d . . . . .
H11A H 0.844517 0.271369 0.715254 0.047 Uiso 1 1 calc R . . . .
H11B H 0.903965 0.290556 0.650992 0.047 Uiso 1 1 calc R . . . .
C14 C 0.97355(10) 0.0324(3) 0.75756(18) 0.0369(5) Uani 1 1 d . . . . .
H14 H 0.998665 0.067801 0.703964 0.044 Uiso 1 1 calc R . . . .
C10 C 0.77865(10) 0.0445(3) 0.56942(19) 0.0394(5) Uani 1 1 d . . . . .
H10 H 0.753131 0.054811 0.626419 0.047 Uiso 1 1 calc R . . . .
C4 C 0.34333(10) 0.3527(3) 0.44190(18) 0.0387(5) Uani 1 1 d . . . . .
H4A H 0.313802 0.254886 0.428093 0.046 Uiso 1 1 calc R . . . .
H4B H 0.341946 0.407937 0.366354 0.046 Uiso 1 1 calc R . . . .
C3 C 0.46082(10) 0.3334(3) 0.44252(19) 0.0404(5) Uani 1 1 d . . . . .
H3 H 0.458624 0.404637 0.377390 0.048 Uiso 1 1 calc R . . . .
C7 C 0.26291(12) 0.4567(3) 0.5516(3) 0.0635(8) Uani 1 1 d . . . . .
H7 H 0.231939 0.371163 0.525003 0.076 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'
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
C1 N3 C4 128.74(17) . .
C1 N3 C3 107.18(17) . .
C3 N3 C4 123.92(18) . .
C14 N11 C13 103.53(16) . .
C9 N9 C11 125.74(17) . .
C9 N9 C10 107.46(17) . .
C10 N9 C11 126.37(18) . .
C12 N10 C11 125.52(17) . .
C12 N10 C14 107.36(17) . .
C14 N10 C11 126.88(18) . .
O8 N12 C13 117.30(17) . .
O7 N12 O8 123.69(18) . .
O7 N12 C13 119.01(16) . .
O4 N6 C6 118.55(17) . .
O3 N6 O4 123.67(18) . .
O3 N6 C6 117.77(16) . .
C5 N4 C4 128.61(16) . .
C7 N4 C5 107.14(17) . .
C7 N4 C4 124.24(18) . .
C10 N8 C8 103.29(18) . .
C3 N2 C2 103.39(17) . .
O2 N1 O1 124.4(2) . .
O2 N1 C2 119.1(2) . .
O1 N1 C2 116.47(18) . .
O5 N7 O6 124.8(2) . .
O5 N7 C8 118.3(2) . .
O6 N7 C8 116.9(2) . .
C7 N5 C6 103.40(18) . .
N4 C5 H5 128.0 . .
C6 C5 N4 104.09(17) . .
C6 C5 H5 128.0 . .
N11 C13 N12 121.45(17) . .
C12 C13 N11 112.65(18) . .
C12 C13 N12 125.89(17) . .
N2 C2 N1 120.33(18) . .
C1 C2 N2 112.38(19) . .
C1 C2 N1 127.23(19) . .
N10 C12 H12 127.9 . .
C13 C12 N10 104.28(16) . .
C13 C12 H12 127.9 . .
N3 C1 C2 104.60(18) . .
N3 C1 H1 127.7 . .
C2 C1 H1 127.7 . .
N5 C6 N6 120.61(17) . .
N5 C6 C5 112.89(19) . .
C5 C6 N6 126.37(18) . .
N8 C8 N7 122.2(2) . .
C9 C8 N8 113.14(18) . .
C9 C8 N7 124.6(2) . .
N9 C9 H9 128.0 . .
C8 C9 N9 104.06(18) . .
C8 C9 H9 128.0 . .
N9 C11 N10 110.35(16) . .
N9 C11 H11A 109.6 . .
N9 C11 H11B 109.6 . .
N10 C11 H11A 109.6 . .
N10 C11 H11B 109.6 . .
H11A C11 H11B 108.1 . .
N11 C14 N10 112.19(18) . .
N11 C14 H14 123.9 . .
N10 C14 H14 123.9 . .
N9 C10 H10 124.0 . .
N8 C10 N9 112.05(19) . .
N8 C10 H10 124.0 . .
N3 C4 N4 111.70(17) . .
N3 C4 H4A 109.3 . .
N3 C4 H4B 109.3 . .
N4 C4 H4A 109.3 . .
N4 C4 H4B 109.3 . .
H4A C4 H4B 107.9 . .
N3 C3 H3 123.8 . .
N2 C3 N3 112.45(19) . .
N2 C3 H3 123.8 . .
N4 C7 H7 123.8 . .
N5 C7 N4 112.4(2) . .
N5 C7 H7 123.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O8 N12 1.229(2) .
O4 N6 1.234(2) .
O7 N12 1.227(2) .
O3 N6 1.231(2) .
N3 C1 1.355(3) .
N3 C4 1.444(3) .
N3 C3 1.360(2) .
N11 C13 1.367(2) .
N11 C14 1.309(3) .
N9 C9 1.359(3) .
N9 C11 1.452(3) .
N9 C10 1.366(3) .
N10 C12 1.360(3) .
N10 C11 1.455(3) .
N10 C14 1.366(2) .
N12 C13 1.429(3) .
O2 N1 1.215(2) .
O1 N1 1.231(3) .
N6 C6 1.426(3) .
N4 C5 1.362(3) .
N4 C4 1.459(3) .
N4 C7 1.350(3) .
N8 C8 1.362(3) .
N8 C10 1.312(3) .
O5 N7 1.225(3) .
N2 C2 1.366(3) .
N2 C3 1.309(3) .
O6 N7 1.236(3) .
N1 C2 1.435(3) .
N7 C8 1.438(3) .
N5 C6 1.352(3) .
N5 C7 1.312(3) .
C5 H5 0.9500 .
C5 C6 1.354(3) .
C13 C12 1.358(3) .
C2 C1 1.357(3) .
C12 H12 0.9500 .
C1 H1 0.9500 .
C8 C9 1.355(3) .
C9 H9 0.9500 .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C14 H14 0.9500 .
C10 H10 0.9500 .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C3 H3 0.9500 .
C7 H7 0.9500 .
