#------------------------------------------------------------------------------
#$Date: 2023-06-08 10:51:32 +0300 (Thu, 08 Jun 2023) $
#$Revision: 284404 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/73/8107312.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_8107312
loop_
_publ_author_name
'Huipeng, Zhao'
'Pengbao, Lian'
'Cai, Cao'
'LiZhen, Chen'
'Jianlong, Wang'
_publ_section_title
;
 The crystal structure of 5-azido-1-methyl-4-nitroimidazole, C4H4O2N6
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1127
_journal_page_last               1128
_journal_paper_doi               10.1515/ncrs-2022-0385
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C4 H4 N6 O2'
_chemical_formula_sum            'C4 H4 N6 O2'
_chemical_formula_weight         168.13
_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
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 105.216(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.633(3)
_cell_length_b                   8.899(3)
_cell_length_c                   6.7638(18)
_cell_measurement_reflns_used    1273
_cell_measurement_temperature    170
_cell_measurement_theta_max      25.84
_cell_measurement_theta_min      2.92
_cell_volume                     675.7(3)
_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      170.0
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_unetI/netI     0.0569
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            4814
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.331
_diffrn_reflns_theta_min         2.921
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_correction_T_min  0.7987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0823 before and 0.0492 after correction. The Ratio of minimum to maximum transmission is 0.8606. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.653
_exptl_crystal_description       plate
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1354
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.1010
_refine_ls_R_factor_gt           0.0607
_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)+(0.0565P)²+0.8679P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1388
_refine_ls_wR_factor_ref         0.1617
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                914
_reflns_number_total             1354
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0385_suppl.cif
_cod_data_source_block           3
_cod_original_cell_volume        675.6(4)
_cod_database_code               8107312
_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   0.997
_shelx_estimated_absorpt_t_min   0.985
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3)
2.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
O1 O 0.3606(2) 0.9455(3) 0.2047(4) 0.0388(7) Uani 1 1 d . . . . .
O2 O 0.2018(2) 1.0539(3) 0.2491(4) 0.0434(7) Uani 1 1 d . . . . .
N6 N 0.2597(2) 0.9410(3) 0.2336(4) 0.0315(7) Uani 1 1 d . . . . .
N4 N 0.1775(2) 0.5581(3) 0.2405(4) 0.0300(7) Uani 1 1 d . . . . .
N5 N 0.0929(2) 0.7820(3) 0.2476(4) 0.0326(7) Uani 1 1 d . . . . .
N2 N 0.4627(3) 0.6857(3) 0.3347(5) 0.0349(7) Uani 1 1 d . . . . .
N1 N 0.3759(2) 0.6082(3) 0.2364(5) 0.0339(7) Uani 1 1 d . . . . .
N3 N 0.5485(3) 0.7402(4) 0.4153(6) 0.0485(9) Uani 1 1 d . . . . .
C1 C 0.2093(3) 0.7975(3) 0.2460(5) 0.0281(7) Uani 1 1 d . . . . .
C2 C 0.2643(3) 0.6616(4) 0.2429(5) 0.0279(7) Uani 1 1 d . . . . .
C3 C 0.0771(3) 0.6361(4) 0.2425(5) 0.0319(8) Uani 1 1 d . . . . .
H3 H 0.003321 0.589586 0.240346 0.038 Uiso 1 1 calc R . . . .
C4 C 0.1907(3) 0.3942(4) 0.2392(6) 0.0358(8) Uani 1 1 d . . . . .
H4A H 0.220754 0.364519 0.122484 0.054 Uiso 1 1 calc GR . . . .
H4B H 0.113169 0.346771 0.227407 0.054 Uiso 1 1 calc GR . . . .
H4C H 0.247008 0.361950 0.366867 0.054 Uiso 1 1 calc GR . . . .
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
O1 N6 C1 117.5(3) . .
O2 N6 O1 123.3(3) . .
O2 N6 C1 119.2(3) . .
C2 N4 C4 126.4(3) . .
C3 N4 C2 106.8(3) . .
C3 N4 C4 126.8(3) . .
C3 N5 C1 103.4(3) . .
N3 N2 N1 170.9(3) . .
N2 N1 C2 114.9(3) . .
N5 C1 N6 121.2(3) . .
N5 C1 C2 112.3(3) . .
C2 C1 N6 126.4(3) . .
N4 C2 N1 117.5(3) . .
N4 C2 C1 104.4(3) . .
C1 C2 N1 138.0(3) . .
N4 C3 H3 123.5 . .
N5 C3 N4 113.0(3) . .
N5 C3 H3 123.5 . .
N4 C4 H4A 109.5 . .
N4 C4 H4B 109.5 . .
N4 C4 H4C 109.5 . .
H4A C4 H4B 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 N6 1.240(3) .
O2 N6 1.229(3) .
N6 C1 1.416(4) .
N4 C2 1.364(4) .
N4 C3 1.361(4) .
N4 C4 1.466(4) .
N5 C1 1.364(4) .
N5 C3 1.311(5) .
N2 N1 1.258(4) .
N2 N3 1.115(4) .
N1 C2 1.395(4) .
C1 C2 1.370(4) .
C3 H3 0.9500 .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
