#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/50/2005067.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_2005067
loop_
_publ_author_name
'Kowalski, A.'
_publ_section_title
;
 1-(p-Methoxyphenyl)-2-methyl-4-nitroimidazole and
 1-(p-Acetylphenyl)-2-methyl-4-nitroimidazole
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1784
_journal_page_last               1787
_journal_paper_doi               10.1107/S0108270196001722
_journal_volume                  52
_journal_year                    1996
_chemical_formula_sum            'C11 H11 N3 O3'
_chemical_formula_weight         233.23
_chemical_name_systematic
;
1-(p-pethoxy-phenyl)-2-methyl-4-nitro-imidazole
;
_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'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.
_cell_angle_beta                 90.83(3)
_cell_angle_gamma                90.
_cell_formula_units_Z            4
_cell_length_a                   12.299(2)
_cell_length_b                   8.046(2)
_cell_length_c                   11.563(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      16
_cell_volume                     1144.1(4)
_computing_data_collection       'Kuma KM-4 User's Guide (Kuma, 1989)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Kuma KM-4 automated four-circle κ-axis'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0105
_diffrn_reflns_av_sigmaI/netI    0.0433
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2514
_diffrn_reflns_theta_max         79.92
_diffrn_reflns_theta_min         3.59
_diffrn_standards_decay_%        3.2
_diffrn_standards_interval_count 50
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.849
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_meas      1.40
_exptl_crystal_density_method    flotation
_exptl_crystal_description       irregular
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.113
_refine_diff_density_min         -0.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.120
_refine_ls_goodness_of_fit_obs   1.251
_refine_ls_hydrogen_treatment    'H atoms refined isotropically'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         2179
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.416
_refine_ls_restrained_S_obs      1.251
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_obs          0.0409
_refine_ls_shift/esd_max         0.630
_refine_ls_shift/esd_mean        0.076
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
;
calc w = 1/[\s^2^(F~o~^2^) + (0.0763P)^2^ + 0.0557P]
where P = (F~o~^2^ + 2F~c~^2^)/3
;
_refine_ls_wR_factor_all         0.1628
_refine_ls_wR_factor_obs         0.1270
_reflns_number_observed          1614
_reflns_number_total             2385
_reflns_observed_criterion       >3sigma(I)
_cod_data_source_file            ab1279.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2005067
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_occupancy
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_type_symbol
O1 1 1.14314(13) 0.3797(3) 0.4787(2) 0.1045(6) Uani d O
O2 1 1.13408(14) 0.3013(3) 0.6554(2) 0.1052(6) Uani d O
O3 1 0.51503(10) 0.1041(2) 0.11819(10) 0.0688(4) Uani d O
N1 1 0.84297(10) 0.1669(2) 0.45103(10) 0.0557(3) Uani d N
N2 1 0.93710(11) 0.1546(2) 0.61565(11) 0.0608(4) Uani d N
N3 1 1.09668(12) 0.3102(2) 0.55785(15) 0.0707(4) Uani d N
C1 1 0.84631(13) 0.1111(2) 0.56381(13) 0.0571(4) Uani d C
C2 1 0.99299(11) 0.2388(2) 0.53389(13) 0.0578(4) Uani d C
C3 1 0.93842(12) 0.2479(2) 0.43074(14) 0.0608(4) Uani d C
C4 1 0.75565(12) 0.1476(2) 0.36824(12) 0.0535(3) Uani d C
C5 1 0.77232(12) 0.0586(2) 0.26773(13) 0.0581(4) Uani d C
C6 1 0.68937(13) 0.0464(2) 0.18695(13) 0.0605(4) Uani d C
C7 1 0.58958(12) 0.1222(2) 0.20567(12) 0.0541(3) Uani d C
C8 1 0.57282(12) 0.2099(2) 0.30668(13) 0.0604(4) Uani d C
C9 1 0.65666(13) 0.2233(2) 0.38762(13) 0.0619(4) Uani d C
C10 1 0.7580(2) 0.0118(3) 0.6157(2) 0.0752(5) Uani d C
C11 1 0.4145(2) 0.1892(4) 0.1276(2) 0.0849(6) Uani d C
H3 1 0.9567(19) 0.3023(29) 0.3532(21) 0.075(5) Uiso d H
H5 1 0.8398(17) 0.0103(25) 0.2528(16) 0.059(4) Uiso d H
H6 1 0.7012(18) -0.0175(31) 0.1128(22) 0.078(6) Uiso d H
H8 1 0.4990(20) 0.2636(28) 0.3174(19) 0.073(5) Uiso d H
H9 1 0.6454(19) 0.2913(30) 0.4605(21) 0.077(6) Uiso d H
H10A 1 0.6903(40) 0.0729(62) 0.6053(42) 0.135(13) Uiso d H
H10B 1 0.7932(54) -0.0660(85) 0.6695(62) 0.177(18) Uiso d H
H10C 1 0.7212(34) -0.0472(51) 0.5530(39) 0.123(11) Uiso d H
H11A 1 0.3736(30) 0.1544(43) 0.0618(33) 0.110(9) Uiso d H
H11B 1 0.4229(35) 0.3090(63) 0.1391(39) 0.134(12) Uiso d H
H11C 1 0.3691(31) 0.1474(44) 0.1995(36) 0.113(10) Uiso d H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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
C7 O3 C11 117.98(14) n
C3 N1 C1 107.69(12) n
C3 N1 C4 124.97(12) n
C1 N1 C4 127.34(13) n
C1 N2 C2 104.58(13) n
O1 N3 O2 123.2(2) n
O2 N3 C2 118.9(2) n
O1 N3 C2 117.8(2) n
N2 C1 N1 111.10(14) n
N2 C1 C10 125.8(2) n
N1 C1 C10 123.13(15) n
N2 C2 C3 112.87(13) n
N2 C2 N3 121.84(14) n
C3 C2 N3 125.29(15) n
C2 C3 N1 103.75(13) n
C5 C4 C9 120.39(13) n
C5 C4 N1 119.83(13) n
C9 C4 N1 119.74(13) n
C6 C5 C4 119.32(14) n
C5 C6 C7 120.68(13) n
O3 C7 C8 125.06(13) n
O3 C7 C6 115.05(13) n
C8 C7 C6 119.88(13) n
C7 C8 C9 119.42(13) n
C4 C9 C8 120.29(13) n
C2 C3 H3 132.3(14) n
N1 C3 H3 124.0(14) n
C6 C5 H5 120.1(12) n
C4 C5 H5 120.4(12) n
C5 C6 H6 119.9(14) n
C7 C6 H6 119.4(14) n
C9 C8 H8 123.2(15) n
C7 C8 H8 117.4(15) n
C4 C9 H9 120.5(15) n
C8 C9 H9 119.2(15) n
C1 C10 H10A 109.(3) n
C1 C10 H10B 106.(3) n
H10A C10 H10B 145.(4) n
C1 C10 H10C 106.(3) n
H10A C10 H10C 82.(3) n
H10B C10 H10C 88.(4) n
O3 C11 H11A 106.(2) n
O3 C11 H11B 111.(3) n
H11A C11 H11B 116.(4) n
O3 C11 H11C 111.(2) n
H10A C11 H11C 104.(3) n
H11B C11 H11C 109.(4) n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 N3 1.221(2) yes
O2 N3 1.214(2) yes
O3 C7 1.363(2) yes
O3 C11 1.419(3) yes
N1 C3 1.366(2) yes
N1 C1 1.379(2) yes
N1 C4 1.437(2) yes
N2 C1 1.307(2) yes
N2 C2 1.358(2) yes
N3 C2 1.423(2) yes
C1 C10 1.482(3) yes
C2 C3 1.362(2) yes
C4 C5 1.383(2) yes
C4 C9 1.382(2) yes
C5 C6 1.377(2) yes
C6 C7 1.390(2) yes
C7 C8 1.383(2) yes
C8 C9 1.387(2) yes
C3 H3 1.101(3) n
C5 H5 0.93(2) n
C6 H6 1.101(3) n
C8 H8 1.02(3) n
C9 H9 1.101(3) n
C10 H10A 0.98(5) n
C10 H10B 1.103(7) n
C10 H10C 0.96(5) n
C11 H11A 0.94(4) n
C11 H11A 0.98(5) n
C11 H11A 1.10(5) n
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2274068
