#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/76/2237698.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_2237698
loop_
_publ_author_name
'Yousuf, Sammer'
'Khan, Khalid M.'
'Naz, Frazana'
'Perveen, Shahanaz'
'Miana, Ghulam A.'
_publ_section_title
;
 1-(2-Methyl-5-nitro-1H-imidazol-1-yl)acetone
;
_journal_coeditor_code           RZ5048
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o552
_journal_paper_doi               10.1107/S1600536813006569
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C7 H9 N3 O3'
_chemical_formula_moiety         'C7 H9 N3 O3'
_chemical_formula_sum            'C7 H9 N3 O3'
_chemical_formula_weight         183.17
_chemical_name_systematic
;
1-(2-Methyl-5-nitro-1H-imidazol-1-yl)acetone
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.350(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.7548(4)
_cell_length_b                   12.3971(9)
_cell_length_c                   14.8580(11)
_cell_measurement_reflns_used    1790
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.65
_cell_measurement_theta_min      2.76
_cell_volume                     868.62(12)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON
(Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type
;
Bruker SMART APEX CCD area-detector
;
_diffrn_measurement_method       'ω scan'
_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  0.0185
_diffrn_reflns_av_sigmaI/netI    0.0184
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5030
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.9737
_exptl_absorpt_correction_T_min  0.9442
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.153
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1614
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0414
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0591P)²+0.2124P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1215
_reflns_number_gt                1328
_reflns_number_total             1614
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz5048.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2237698
_cod_database_fobs_code          2237698
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_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_symmetry_multiplicity
O O1 -0.1621(4) 0.29596(12) 0.33611(13) 0.0887(5) Uani d . 1 1
O O2 0.1562(3) 0.37418(11) 0.26792(12) 0.0791(5) Uani d . 1 1
O O3 -0.2465(3) 0.53369(11) 0.15962(9) 0.0622(4) Uani d . 1 1
N N1 -0.0008(3) 0.57463(11) 0.33181(9) 0.0424(4) Uani d . 1 1
N N2 -0.2805(3) 0.59824(13) 0.43940(10) 0.0574(4) Uani d . 1 1
N N3 -0.0337(3) 0.37691(12) 0.31638(12) 0.0589(4) Uani d . 1 1
C C1 -0.1098(3) 0.47575(13) 0.35252(12) 0.0464(4) Uani d . 1 1
C C2 -0.2784(4) 0.49243(16) 0.41793(12) 0.0554(5) Uani d . 1 1
H H2B -0.3781 0.4389 0.4442 0.067 Uiso calc R 1 1
C C3 -0.1137(4) 0.64611(14) 0.38648(11) 0.0485(4) Uani d . 1 1
C C4 -0.0467(5) 0.76284(16) 0.38973(15) 0.0728(6) Uani d . 1 1
H H4A -0.1214 0.7951 0.4404 0.109 Uiso calc R 1 1
H H4B -0.1305 0.7965 0.3346 0.109 Uiso calc R 1 1
H H4C 0.1552 0.7725 0.3963 0.109 Uiso calc R 1 1
C C5 0.1509(3) 0.60187(13) 0.25566(11) 0.0444(4) Uani d . 1 1
H H5A 0.3240 0.5598 0.2597 0.053 Uiso calc R 1 1
H H5B 0.2034 0.6775 0.2595 0.053 Uiso calc R 1 1
C C6 -0.0235(3) 0.58087(13) 0.16507(12) 0.0451(4) Uani d . 1 1
C C7 0.1011(4) 0.62131(17) 0.08469(13) 0.0653(5) Uani d . 1 1
H H7A -0.0270 0.6069 0.0307 0.098 Uiso calc R 1 1
H H7B 0.2783 0.5855 0.0810 0.098 Uiso calc R 1 1
H H7C 0.1326 0.6976 0.0905 0.098 Uiso calc R 1 1
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
C3 N1 C1 104.93(14)
C3 N1 C5 125.87(14)
C1 N1 C5 128.02(14)
C3 N2 C2 105.74(15)
O2 N3 O1 122.92(17)
O2 N3 C1 119.63(15)
O1 N3 C1 117.45(17)
C2 C1 N1 107.35(15)
C2 C1 N3 127.87(16)
N1 C1 N3 124.56(15)
N2 C2 C1 109.97(15)
N2 C2 H2B 125.0
C1 C2 H2B 125.0
N2 C3 N1 112.01(16)
N2 C3 C4 124.07(16)
N1 C3 C4 123.86(16)
C3 C4 H4A 109.5
C3 C4 H4B 109.5
H4A C4 H4B 109.5
C3 C4 H4C 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
N1 C5 C6 112.47(13)
N1 C5 H5A 109.1
C6 C5 H5A 109.1
N1 C5 H5B 109.1
C6 C5 H5B 109.1
H5A C5 H5B 107.8
O3 C6 C7 123.21(16)
O3 C6 C5 121.44(15)
C7 C6 C5 115.35(14)
C6 C7 H7A 109.5
C6 C7 H7B 109.5
H7A C7 H7B 109.5
C6 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N3 1.230(2)
O2 N3 1.225(2)
O3 C6 1.205(2)
N1 C3 1.358(2)
N1 C1 1.381(2)
N1 C5 1.457(2)
N2 C3 1.326(2)
N2 C2 1.350(3)
N3 C1 1.404(2)
C1 C2 1.352(2)
C2 H2B 0.9300
C3 C4 1.481(3)
C4 H4A 0.9600
C4 H4B 0.9600
C4 H4C 0.9600
C5 C6 1.510(2)
C5 H5A 0.9700
C5 H5B 0.9700
C6 C7 1.486(3)
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
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
C2 H2B N2 3_466 0.9300 2.5600 3.361(2) 144.00 yes
C5 H5B O2 2_555 0.9700 2.5700 3.527(2) 167.00 yes
C7 H7B O3 1_655 0.9600 2.4900 3.340(2) 147.00 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
C3 N1 C1 C2 -0.39(18)
C5 N1 C1 C2 -168.41(15)
C3 N1 C1 N3 -175.31(16)
C5 N1 C1 N3 16.7(3)
O2 N3 C1 C2 -168.38(18)
O1 N3 C1 C2 11.0(3)
O2 N3 C1 N1 5.5(3)
O1 N3 C1 N1 -175.14(16)
C3 N2 C2 C1 0.3(2)
N1 C1 C2 N2 0.1(2)
N3 C1 C2 N2 174.76(17)
C2 N2 C3 N1 -0.6(2)
C2 N2 C3 C4 -177.73(19)
C1 N1 C3 N2 0.60(18)
C5 N1 C3 N2 168.96(14)
C1 N1 C3 C4 177.77(18)
C5 N1 C3 C4 -13.9(3)
C3 N1 C5 C6 -106.10(18)
C1 N1 C5 C6 59.6(2)
N1 C5 C6 O3 -9.0(2)
N1 C5 C6 C7 171.59(15)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 129973
