#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/17/2011706.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_2011706
loop_
_publ_author_name
'Kubicki, Maciej'
'Borowiak, Teresa'
'Suwiński, Jerzy'
'Wagner, Paweł'
_publ_section_title
;
 Two 1-substituted 4-nitroimidazoles
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              106
_journal_page_last               108
_journal_paper_doi               10.1107/S0108270100014852
_journal_volume                  57
_journal_year                    2001
_chemical_formula_moiety         'C12 H9 N5 O2'
_chemical_formula_sum            'C12 H9 N5 O2'
_chemical_formula_weight         255.24
_chemical_melting_point          '209-211 (methanol)'
_chemical_name_systematic
;
 1-(1-phenyl-4-imidazolyl)-4-nitroimidazole
;
_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-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.92(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.143(3)
_cell_length_b                   3.8880(10)
_cell_length_c                   20.660(4)
_cell_measurement_reflns_used    531
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      50
_cell_measurement_theta_min      1
_cell_volume                     1131.9(4)
_computing_cell_refinement       'CrysAlis CCD'
_computing_data_collection       'CrysAlis CCD  (KUMA Diffraction, 1999)'
_computing_data_reduction        'CrysAlis CCD'
_computing_molecular_graphics    'Stereochemical workstation (Siemens 1989)'
_computing_publication_material  'Stereochemical workstation'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      301
_diffrn_measured_fraction_theta_full .923
_diffrn_measured_fraction_theta_max .923
_diffrn_measurement_device_type  'KUMA KM4 CCD'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .0560
_diffrn_reflns_av_sigmaI/netI    .1347
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            6713
_diffrn_reflns_theta_full        29.35
_diffrn_reflns_theta_max         29.35
_diffrn_reflns_theta_min         3.36
_diffrn_standards_decay_%        'not measured'
_diffrn_standards_interval_count '50 frames'
_diffrn_standards_number         '2 frames'
_exptl_absorpt_coefficient_mu    .108
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             528
_exptl_crystal_size_max          .4
_exptl_crystal_size_mid          .2
_exptl_crystal_size_min          .02
_refine_diff_density_max         .156
_refine_diff_density_min         -.173
_refine_ls_extinction_coef       .0034(10)
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   .781
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2882
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      .781
_refine_ls_R_factor_all          .1627
_refine_ls_R_factor_gt           .0456
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0453P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1047
_reflns_number_gt                1046
_reflns_number_total             2882
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            de1151.cif
_cod_data_source_block           II
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2011706
_cod_database_fobs_code          2011706
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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
N6 .23611(11) .0437(4) .39758(7) .0412(4) Uani d . 1 . . N
N1 .01115(11) -.3600(4) .37315(7) .0398(4) Uani d . 1 . . N
C4 -.13052(14) -.5578(6) .36235(9) .0443(6) Uani d . 1 . . C
N3 -.09174(13) -.6482(4) .30671(8) .0490(5) Uani d . 1 . . N
C9 .09675(15) -.1879(5) .39356(10) .0398(5) Uani d . 1 . . C
C10 .16838(15) -.1183(6) .35678(11) .0437(6) Uani d . 1 . . C
N8 .11439(13) -.0749(5) .45543(8) .0536(5) Uani d . 1 . . N
N17 -.22617(13) -.6559(5) .37163(10) .0589(5) Uani d . 1 . . N
C11 .32471(14) .1763(5) .38106(10) .0425(5) Uani d . 1 . . C
C5 -.06947(15) -.3834(6) .40436(11) .0449(6) Uani d . 1 . . C
O2 -.26021(10) -.5573(5) .42069(8) .0794(6) Uani d . 1 . . O
C7 .19943(18) .0634(6) .45584(11) .0556(7) Uani d . 1 . . C
C2 -.00587(18) -.5220(6) .31513(10) .0468(6) Uani d . 1 . . C
O1 -.26964(12) -.8270(5) .32952(9) .0891(7) Uani d . 1 . . O
C12 .33392(17) .2862(6) .31788(11) .0492(6) Uani d . 1 . . C
C16 .40009(17) .1998(6) .42756(12) .0553(7) Uani d . 1 . . C
C14 .49497(19) .4421(7) .34865(14) .0615(7) Uani d . 1 . . C
C13 .41958(18) .4194(6) .30233(13) .0574(7) Uani d . 1 . . C
C15 .48545(19) .3308(7) .41093(15) .0658(8) Uani d . 1 . . C
H161 .3937(15) .111(5) .4708(11) .069(7) Uiso d . 1 . . H
H71 .2321(13) .173(5) .4928(9) .047(6) Uiso d . 1 . . H
H101 .1734(13) -.159(5) .3134(10) .056(6) Uiso d . 1 . . H
H51 -.0762(13) -.283(5) .4459(10) .051(6) Uiso d . 1 . . H
H21 .0414(14) -.534(5) .2846(9) .055(6) Uiso d . 1 . . H
H121 .2758(15) .271(5) .2842(10) .063(7) Uiso d . 1 . . H
H141 .5522(16) .532(6) .3366(10) .070(7) Uiso d . 1 . . H
H131 .4236(15) .500(6) .2571(11) .083(8) Uiso d . 1 . . H
H151 .5351(16) .347(5) .4434(11) .070(8) Uiso d . 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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
C7 N6 C10 105.75(19) ?
C7 N6 C11 127.3(2) ?
C10 N6 C11 126.94(17) ?
C2 N1 C5 107.17(18) ?
C2 N1 C9 124.39(17) ?
C5 N1 C9 128.37(17) ?
C5 C4 N3 112.94(19) ?
C5 C4 N17 127.2(2) ?
N3 C4 N17 119.8(2) ?
C2 N3 C4 103.16(18) ?
C10 C9 N8 112.41(19) ?
C10 C9 N1 126.39(18) ?
N8 C9 N1 121.20(18) ?
C9 C10 N6 105.36(18) ?
C7 N8 C9 103.46(18) ?
O1 N17 O2 123.6(2) ?
O1 N17 C4 118.3(2) ?
O2 N17 C4 118.1(2) ?
C16 C11 C12 120.4(2) yes
C16 C11 N6 120.14(19) ?
C12 C11 N6 119.5(2) ?
C4 C5 N1 104.14(19) ?
N8 C7 N6 113.0(2) ?
N3 C2 N1 112.6(2) ?
C13 C12 C11 119.2(2) ?
C11 C16 C15 119.5(2) ?
C13 C14 C15 120.0(3) ?
C14 C13 C12 120.4(2) ?
C14 C15 C16 120.5(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N6 C7 . 1.353(2) yes
N6 C10 . 1.374(2) yes
N6 C11 . 1.423(2) yes
N1 C2 . 1.357(2) yes
N1 C5 . 1.360(2) yes
N1 C9 . 1.415(2) yes
C4 C5 . 1.353(3) yes
C4 N3 . 1.362(2) yes
C4 N17 . 1.434(3) ?
N3 C2 . 1.308(3) yes
C9 C10 . 1.345(3) yes
C9 N8 . 1.354(2) yes
N8 C7 . 1.317(3) yes
N17 O1 . 1.219(2) ?
N17 O2 . 1.220(2) ?
C11 C16 . 1.376(3) ?
C11 C12 . 1.390(3) ?
C12 C13 . 1.381(3) ?
C16 C15 . 1.381(3) ?
C14 C13 . 1.373(3) ?
C14 C15 . 1.375(3) ?
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
C7 H71 O2 3_556 .959(19) 2.34(2) 3.249(3) 158.9(15)
C5 H51 N8 3_556 .955(19) 2.56(2) 3.505(3) 168.7(15)
C2 H21 N3 2 .959(19) 2.56(2) 3.309(3) 135.2(16)
C10 H101 N3 2 .919(19) 2.65(2) 3.460(3) 148.0(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21135389
