#------------------------------------------------------------------------------
#$Date: 2023-02-01 09:56:18 +0100 (Wed 01 de Feb de 2023) $
#$Revision: 280726 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/66/8106647.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_8106647
loop_
_publ_author_name
'Jianlong, Wang'
'Pengbao, Lian'
'Lizhen, Chen'
_publ_section_title
;
 Crystal structure of the triclinic modification of
 1-methyl-4-nitroimidzole, C4H5N3O2
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              699
_journal_page_last               700
_journal_paper_doi               10.1515/ncrs-2017-0020
_journal_volume                  232
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C4 H5 N3 O2'
_chemical_formula_sum            'C4 H5 N3 O2'
_chemical_formula_weight         127.11
_chemical_melting_point          407.45
_chemical_name_common            1-methyl-4-nitroimidzole
_chemical_name_systematic
;
1-methyl-4-nitroimidzole 
;
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                89.630(12)
_cell_angle_beta                 84.800(13)
_cell_angle_gamma                76.970(13)
_cell_formula_units_Z            1
_cell_length_a                   3.8976(6)
_cell_length_b                   5.7235(8)
_cell_length_c                   6.2670(10)
_cell_measurement_reflns_used    834
_cell_measurement_temperature    104.8
_cell_measurement_theta_max      28.9069
_cell_measurement_theta_min      3.2730
_cell_volume                     135.63(4)
_computing_cell_refinement       'CrysAlisPro [1]'
_computing_data_collection       'CrysAlisPro [1]'
_computing_data_reduction        'CrysAlisPro [1]'
_computing_molecular_graphics    'OLEX2 [3]'
_computing_publication_material  'OLEX2 [3]'
_computing_structure_refinement  'SHELXL-97 [2]'
_computing_structure_solution    'SHELXS-2007 [2]'
_diffrn_ambient_temperature      104.8
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0323
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            1610
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.26
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50354
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro, Agilent Technologies,Version 1.171.35.11 
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             66
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     83
_refine_ls_number_reflns         1062
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0519
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
w=1/[σ²(Fo²)+(0.0831P)²+0.0000P]
  where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1277
_refine_ls_wR_factor_ref         0.1303
_reflns_number_gt                1018
_reflns_number_total             1062
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2017-0020_suppl.cif
_cod_data_source_block           exp_01
_cod_database_code               8106647
_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_operation_xyz
'x, y, z'
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
N2 N -0.4443(6) -0.1521(5) -0.5265(4) 0.0210(6) Uani 1 1 d . . .
N3 N -0.1740(6) -0.0846(4) -0.2030(4) 0.0226(6) Uani 1 1 d . . .
O1 O -0.0785(6) 0.0609(4) -0.0913(3) 0.0292(6) Uani 1 1 d . . .
O2 O -0.1321(6) -0.3008(4) -0.1614(4) 0.0344(6) Uani 1 1 d . . .
C3 C -0.4190(7) 0.2372(5) -0.4574(5) 0.0207(6) Uani 1 1 d . . .
H3 H -0.3748 0.3743 -0.3901 0.025 Uiso 1 1 calc R . .
N1 N -0.5720(6) 0.2260(4) -0.6438(4) 0.0199(6) Uani 1 1 d . . .
C4 C -0.7062(8) 0.4237(5) -0.7864(5) 0.0247(7) Uani 1 1 d . . .
H4A H -0.5099 0.4916 -0.8470 0.037 Uiso 1 1 calc R . .
H4B H -0.8820 0.5482 -0.7048 0.037 Uiso 1 1 calc R . .
H4C H -0.8162 0.3631 -0.9025 0.037 Uiso 1 1 calc R . .
C1 C -0.5821(7) -0.0088(5) -0.6771(5) 0.0223(6) Uani 1 1 d . . .
H1 H -0.6785 -0.0626 -0.7966 0.027 Uiso 1 1 calc R . .
C2 C -0.3441(7) 0.0029(5) -0.3899(5) 0.0194(7) Uani 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N2 0.0256(12) 0.0130(13) 0.0245(13) 0.0031(11) -0.0055(10) -0.0034(9)
N3 0.0281(12) 0.0180(14) 0.0229(12) 0.0049(10) -0.0042(10) -0.0069(11)
O1 0.0390(11) 0.0250(12) 0.0269(11) -0.0016(9) -0.0051(9) -0.0130(10)
O2 0.0494(15) 0.0183(13) 0.0368(12) 0.0108(10) -0.0103(11) -0.0084(11)
C3 0.0245(14) 0.0119(13) 0.0262(15) 0.0005(11) -0.0013(11) -0.0059(10)
N1 0.0243(13) 0.0103(11) 0.0261(13) 0.0029(9) -0.0021(10) -0.0060(9)
C4 0.0297(17) 0.0121(14) 0.0321(16) 0.0050(12) -0.0049(12) -0.0037(11)
C1 0.0256(14) 0.0155(14) 0.0265(15) -0.0005(11) -0.0019(12) -0.0063(11)
C2 0.0218(12) 0.0140(16) 0.0213(13) 0.0009(11) 0.0005(10) -0.0028(11)
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 N2 C2 102.8(2) . .
O1 N3 O2 123.6(3) . .
O1 N3 C2 117.7(2) . .
O2 N3 C2 118.7(2) . .
N1 C3 H3 128.1 . .
N1 C3 C2 103.8(2) . .
C2 C3 H3 128.1 . .
C3 N1 C4 127.9(2) . .
C3 N1 C1 107.4(2) . .
C1 N1 C4 124.7(2) . .
N1 C4 H4A 109.5 . .
N1 C4 H4B 109.5 . .
N1 C4 H4C 109.5 . .
H4A C4 H4B 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
N2 C1 N1 113.1(2) . .
N2 C1 H1 123.5 . .
N1 C1 H1 123.5 . .
N2 C2 N3 120.6(2) . .
N2 C2 C3 112.9(3) . .
C3 C2 N3 126.5(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N2 C1 1.317(4) .
N2 C2 1.378(4) .
N3 O1 1.231(3) .
N3 O2 1.240(3) .
N3 C2 1.430(4) .
C3 H3 0.9500 .
C3 N1 1.367(4) .
C3 C2 1.378(4) .
N1 C4 1.469(3) .
N1 C1 1.371(4) .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
C1 H1 0.9500 .
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
O1 N3 C2 N2 177.3(3) . . . .
O1 N3 C2 C3 -1.2(3) . . . .
O2 N3 C2 N2 -3.0(3) . . . .
O2 N3 C2 C3 178.4(3) . . . .
C3 N1 C1 N2 -0.4(3) . . . .
N1 C3 C2 N2 0.0(3) . . . .
N1 C3 C2 N3 178.6(2) . . . .
C4 N1 C1 N2 179.9(3) . . . .
C1 N2 C2 N3 -178.9(2) . . . .
C1 N2 C2 C3 -0.2(3) . . . .
C2 N2 C1 N1 0.4(3) . . . .
C2 C3 N1 C4 180.0(2) . . . .
C2 C3 N1 C1 0.3(3) . . . .
