#------------------------------------------------------------------------------
#$Date: 2017-10-13 08:09:21 +0200 (vie 13 de oct de 2017) $
#$Revision: 201973 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/71/2207153.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2207153
loop_
_publ_author_name
'Wu, Hai-Qiang'
'Liu, Zhi-Gang'
'Ng, Seik Weng'
_publ_section_title
;
 1-Methyl-4-nitro-1H-imidazole-2-carboxylic acid dihydrate
;
_journal_coeditor_code           BT6758
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3759
_journal_page_last               o3760
_journal_paper_doi               10.1107/S1600536805032800
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C5 H5 N3 O4, 2H2 O'
_chemical_formula_moiety         'C5 H5 N3 O4, 2H2 O'
_chemical_formula_sum            'C5 H9 N3 O6'
_chemical_formula_weight         207.15
_chemical_name_systematic
;
1-Methyl-4-nitro-1H-imidazole-2-carboxylic acid dihydrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 97.735(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5163(9)
_cell_length_b                   12.199(2)
_cell_length_c                   9.7300(10)
_cell_measurement_reflns_used    890
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.0
_cell_measurement_theta_min      2.7
_cell_volume                     884.0(2)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type  'Bruker SMART area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.015
_diffrn_reflns_av_sigmaI/netI    0.018
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5110
_diffrn_reflns_theta_full        27.0
_diffrn_reflns_theta_max         27.0
_diffrn_reflns_theta_min         2.7
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Prism
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Yellow
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.33
_refine_diff_density_min         -0.16
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.02
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         1931
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.02
_refine_ls_R_factor_all          0.049
_refine_ls_R_factor_gt           0.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0631P)²+0.1428P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.099
_refine_ls_wR_factor_ref         0.109
_reflns_number_gt                1504
_reflns_number_total             1931
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6758.cif
_cod_data_source_block           I
_cod_original_cell_volume        884.1(2)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2207153
_cod_database_fobs_code          2207153
loop_
_symmetry_equiv_pos_as_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_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
O1 0.8235(2) 0.31330(10) 0.53680(10) 0.0548(3) Uani d . 1 O
O2 0.6369(2) 0.29300(10) 0.34070(10) 0.0664(4) Uani d . 1 O
O4 0.8741(2) 0.71780(10) 0.68230(10) 0.0645(4) Uani d . 1 O
O3 0.7244(2) 0.81950(10) 0.5274(2) 0.0734(4) Uani d . 1 O
O1w 0.9850(2) 0.45930(10) 0.78280(10) 0.0552(3) Uani d D 1 O
O2w 1.1566(2) 0.60510(10) 0.97220(10) 0.0561(3) Uani d D 1 O
N1 0.7771(2) 0.53390(10) 0.53140(10) 0.0371(3) Uani d . 1 N
N2 0.6005(2) 0.52940(10) 0.32860(10) 0.0388(3) Uani d . 1 N
N3 0.7781(2) 0.73050(10) 0.57220(10) 0.0488(3) Uani d . 1 N
C1 0.7169(2) 0.34910(10) 0.43010(10) 0.0410(3) Uani d . 1 C
C2 0.7002(2) 0.47040(10) 0.43060(10) 0.0366(3) Uani d . 1 C
C3 0.4954(2) 0.4899(2) 0.1997(2) 0.0525(4) Uani d . 1 C
C4 0.6150(2) 0.63580(10) 0.3659(2) 0.0426(3) Uani d . 1 C
C5 0.7237(2) 0.63590(10) 0.49010(10) 0.0390(3) Uani d . 1 C
H1 0.8254 0.2461 0.5354 0.086(7) Uiso calc R 1 H
H1w1 0.924(2) 0.481(2) 0.7070(10) 0.073(6) Uiso d D 1 H
H1w2 1.027(3) 0.3970(10) 0.772(2) 0.080(7) Uiso d D 1 H
H2w1 1.098(2) 0.571(2) 0.9050(10) 0.070(6) Uiso d D 1 H
H2w2 1.124(3) 0.584(2) 1.0470(10) 0.084(7) Uiso d D 1 H
H3a 0.4468 0.5514 0.1456 0.077(6) Uiso calc R 1 H
H3b 0.3990 0.4443 0.2219 0.074(6) Uiso calc R 1 H
H3c 0.5716 0.4482 0.1476 0.076(6) Uiso calc R 1 H
H4 0.5624 0.6959 0.3176 0.044(4) Uiso calc R 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0710(10) 0.0350(10) 0.0530(10) 0.0050(10) -0.0130(10) 0.0000(10)
O2 0.0820(10) 0.0470(10) 0.0620(10) -0.0010(10) -0.0210(10) -0.0150(10)
O4 0.0810(10) 0.0520(10) 0.0550(10) -0.0030(10) -0.0120(10) -0.0110(10)
O3 0.0900(10) 0.0360(10) 0.0900(10) 0.0040(10) -0.0070(10) 0.0020(10)
O1w 0.0700(10) 0.0490(10) 0.0420(10) 0.0070(10) -0.0110(10) -0.0010(10)
O2w 0.0700(10) 0.0420(10) 0.0540(10) -0.0130(10) 0.0000(10) -0.0010(10)
N1 0.0400(10) 0.0350(10) 0.0350(10) 0.0000(10) 0.0010(10) 0.0000(10)
N2 0.0380(10) 0.0440(10) 0.0330(10) 0.0010(10) 0.0000(10) 0.0020(10)
N3 0.0520(10) 0.0390(10) 0.0550(10) -0.0030(10) 0.0050(10) -0.0030(10)
C1 0.0440(10) 0.0390(10) 0.0390(10) 0.0000(10) 0.0010(10) -0.0040(10)
C2 0.0370(10) 0.0380(10) 0.0340(10) 0.0000(10) 0.0020(10) 0.0000(10)
C3 0.0510(10) 0.0670(10) 0.0360(10) 0.0020(10) -0.0090(10) 0.0010(10)
C4 0.0440(10) 0.0400(10) 0.0440(10) 0.0050(10) 0.0040(10) 0.0070(10)
C5 0.0420(10) 0.0340(10) 0.0410(10) 0.0000(10) 0.0050(10) 0.0010(10)
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_publ_flag
C2 N1 C5 103.70(10) yes
C4 N2 C2 107.20(10) yes
C4 N2 C3 124.00(10) yes
C2 N2 C3 128.80(10) yes
O3 N3 O4 123.80(10) yes
O3 N3 C5 117.60(10) yes
O4 N3 C5 118.60(10) yes
O2 C1 O1 125.60(10) yes
O2 C1 C2 122.40(10) yes
O1 C1 C2 112.10(10) yes
N1 C2 N2 111.90(10) yes
N1 C2 C1 123.90(10) yes
N2 C2 C1 124.20(10) yes
N2 C4 C5 104.90(10) yes
N1 C5 C4 112.30(10) yes
N1 C5 N3 121.70(10) yes
C4 C5 N3 126.00(10) yes
C1 O1 H1 109.5 no
H1w1 O1w H1w2 109.0(10) no
H2w1 O2w H2w2 110.0(10) no
N2 C3 H3a 109.5 no
N2 C3 H3b 109.5 no
H3a C3 H3b 109.5 no
N2 C3 H3c 109.5 no
H3a C3 H3c 109.5 no
H3b C3 H3c 109.5 no
N2 C4 H4 127.6 no
C5 C4 H4 127.6 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 1.299(2) yes
O2 C1 1.203(2) yes
O4 N3 1.220(2) yes
O3 N3 1.217(2) yes
N1 C2 1.321(2) yes
N1 C5 1.352(2) yes
N2 C4 1.348(2) yes
N2 C2 1.365(2) yes
N2 C3 1.470(2) yes
N3 C5 1.431(2) yes
C1 C2 1.485(2) yes
C4 C5 1.365(2) yes
O1 H1 0.82 no
O1w H1w1 0.850(10) no
O1w H1w2 0.840(10) no
O2w H2w1 0.850(10) no
O2w H2w2 0.840(10) no
C3 H3a 0.96 no
C3 H3b 0.96 no
C3 H3c 0.96 no
C4 H4 0.93 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 O2w 2_746 0.82 1.73 2.546(2) 176 yes
O1w H1w1 N1 . 0.850(10) 2.020(10) 2.868(2) 179(2) yes
O1w H1w2 O4 2_746 0.840(10) 2.330(10) 3.134(2) 161(2) yes
O2w H2w1 O1w . 0.850(10) 1.930(10) 2.754(2) 165(2) yes
O2w H2w2 O1w 3_767 0.840(10) 2.010(10) 2.848(2) 173(2) yes
C4 H4 O2 2_655 0.93 2.32 3.206(2) 158 yes
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_publ_flag
C5 N1 C2 N2 -0.2(2) no
C5 N1 C2 C1 -178.90(10) no
C4 N2 C2 N1 0.2(2) no
C3 N2 C2 N1 179.80(10) no
C4 N2 C2 C1 178.90(10) no
C3 N2 C2 C1 -1.5(2) no
O2 C1 C2 N1 175.7(2) no
O1 C1 C2 N1 -3.3(2) no
O2 C1 C2 N2 -2.9(2) no
O1 C1 C2 N2 178.10(10) no
C2 N2 C4 C5 -0.1(2) no
C3 N2 C4 C5 -179.70(10) no
C2 N1 C5 C4 0.2(2) no
C2 N1 C5 N3 179.70(10) no
N2 C4 C5 N1 0.0(2) no
N2 C4 C5 N3 -179.60(10) no
O3 N3 C5 N1 179.90(10) no
O4 N3 C5 N1 -0.5(2) no
O3 N3 C5 C4 -0.7(2) no
O4 N3 C5 C4 179.00(10) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21128659
