#------------------------------------------------------------------------------
#$Date: 2018-02-24 09:33:37 +0200 (Sat, 24 Feb 2018) $
#$Revision: 206646 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/23/2242395.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_2242395
loop_
_publ_author_name
'Osorio, Luis F. B.'
'Carvalho, Samir A.'
'da Silva, Edson F.'
'Fraga, Carlos A. M.'
'Wardell, Solange M. S. V.'
'Milne, Bruce F.'
'Wardell, James L.'
'Harrison, William T. A.'
_publ_section_title
;
 Different molecular conformations in the crystal structures of three
 5-nitroimidazolyl derivatives
;
_journal_coeditor_code           MW2136
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              380
_journal_page_last               384
_journal_paper_doi               10.1107/S2056989018002876
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C12 H11 F N4 O3'
_chemical_formula_moiety         'C12 H11 F N4 O3'
_chemical_formula_sum            'C12 H11 F N4 O3'
_chemical_formula_weight         278.25
_chemical_name_systematic
;
(E)-1-Methyl-5-nitro-1H-imidazole-2-carbaldehyde
O-(4-fluorobenzyl) oxime
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_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
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 102.988(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5484(2)
_cell_length_b                   12.6442(4)
_cell_length_c                   13.4150(9)
_cell_measurement_reflns_used    7472
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     1247.62(10)
_computing_cell_refinement
;
CrystalClear (Rigaku, 2012)
;
_computing_data_collection
;
CrystalClear (Rigaku, 2012)
;
_computing_data_reduction
;
CrystalClear (Rigaku, 2012)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Saturn724+ CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8522
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_min         3.117
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.802
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(FS_ABSCOR; Rigaku, 2013)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.180
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2848
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0338
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0501P)²+0.1808P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.0943
_reflns_number_gt                2292
_reflns_number_total             2848
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            mw2136sup1.cif
_cod_data_source_block           II
_cod_database_code               2242395
_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.
;
_shelx_estimated_absorpt_t_min   0.978
_shelx_estimated_absorpt_t_max   0.988
loop_
_space_group_symop_operation_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_occupancy
C C1 0.40044(15) 0.59196(9) 0.16775(9) 0.0177(2) Uani d 1
C C2 0.38559(16) 0.48697(9) 0.14129(9) 0.0192(3) Uani d 1
H H2 0.3923 0.4590 0.0765 0.023 Uiso calc 1
C C3 0.35720(15) 0.49975(9) 0.29626(9) 0.0160(2) Uani d 1
C C4 0.40828(17) 0.69554(9) 0.33328(9) 0.0213(3) Uani d 1
H H4A 0.3204 0.7499 0.3025 0.032 Uiso calc 1
H H4B 0.5320 0.7228 0.3401 0.032 Uiso calc 1
H H4C 0.3892 0.6769 0.4010 0.032 Uiso calc 1
C C5 0.32784(15) 0.46335(9) 0.39394(9) 0.0176(2) Uani d 1
H H5 0.3457 0.3906 0.4109 0.021 Uiso calc 1
C C6 0.18665(15) 0.54029(9) 0.60895(9) 0.0185(2) Uani d 1
H H6A 0.0718 0.5716 0.5697 0.022 Uiso calc 1
H H6B 0.2737 0.5984 0.6330 0.022 Uiso calc 1
C C7 0.15188(14) 0.47943(9) 0.69873(9) 0.0175(2) Uani d 1
C C8 0.10500(15) 0.37210(9) 0.69078(9) 0.0201(3) Uani d 1
H H8 0.1018 0.3354 0.6286 0.024 Uiso calc 1
C C9 0.06311(16) 0.31892(10) 0.77312(10) 0.0238(3) Uani d 1
H H9 0.0328 0.2459 0.7684 0.029 Uiso calc 1
C C10 0.06662(16) 0.37454(11) 0.86169(10) 0.0249(3) Uani d 1
C C11 0.11210(17) 0.48020(11) 0.87283(9) 0.0250(3) Uani d 1
H H11 0.1132 0.5165 0.9350 0.030 Uiso calc 1
C C12 0.15620(16) 0.53179(10) 0.79027(9) 0.0210(3) Uani d 1
H H12 0.1900 0.6043 0.7965 0.025 Uiso calc 1
N N1 0.36001(13) 0.42969(8) 0.22186(7) 0.0187(2) Uani d 1
N N2 0.38326(12) 0.60100(7) 0.26758(7) 0.0160(2) Uani d 1
N N3 0.27904(12) 0.52518(8) 0.45773(7) 0.0180(2) Uani d 1
N N4 0.42710(14) 0.67827(8) 0.10515(8) 0.0225(2) Uani d 1
O O1 0.26029(11) 0.46915(6) 0.54488(6) 0.01878(19) Uani d 1
O O2 0.44180(14) 0.76801(7) 0.14148(7) 0.0315(2) Uani d 1
O O3 0.43216(14) 0.65795(8) 0.01587(7) 0.0338(2) Uani d 1
F F1 0.02098(11) 0.32309(7) 0.94206(6) 0.0378(2) Uani d 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'
F F 0.0171 0.0103 '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
C2 C1 N2 108.14(10)
C2 C1 N4 127.25(11)
N2 C1 N4 124.60(10)
N1 C2 C1 109.26(10)
N1 C2 H2 125.4
C1 C2 H2 125.4
N1 C3 N2 112.56(10)
N1 C3 C5 119.63(10)
N2 C3 C5 127.81(10)
N2 C4 H4A 109.5
N2 C4 H4B 109.5
H4A C4 H4B 109.5
N2 C4 H4C 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
N3 C5 C3 122.53(11)
N3 C5 H5 118.7
C3 C5 H5 118.7
O1 C6 C7 108.62(9)
O1 C6 H6A 110.0
C7 C6 H6A 110.0
O1 C6 H6B 110.0
C7 C6 H6B 110.0
H6A C6 H6B 108.3
C12 C7 C8 118.98(11)
C12 C7 C6 119.43(10)
C8 C7 C6 121.49(11)
C9 C8 C7 120.48(11)
C9 C8 H8 119.8
C7 C8 H8 119.8
C10 C9 C8 118.41(12)
C10 C9 H9 120.8
C8 C9 H9 120.8
F1 C10 C9 118.57(12)
F1 C10 C11 118.42(12)
C9 C10 C11 123.01(12)
C10 C11 C12 117.84(12)
C10 C11 H11 121.1
C12 C11 H11 121.1
C11 C12 C7 121.26(11)
C11 C12 H12 119.4
C7 C12 H12 119.4
C3 N1 C2 105.71(10)
C3 N2 C1 104.31(9)
C3 N2 C4 126.92(10)
C1 N2 C4 128.42(10)
C5 N3 O1 110.43(9)
O2 N4 O3 123.85(11)
O2 N4 C1 119.16(10)
O3 N4 C1 116.99(10)
N3 O1 C6 107.89(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.3721(16)
C1 N2 1.3789(15)
C1 N4 1.4187(15)
C2 N1 1.3506(15)
C2 H2 0.9500
C3 N1 1.3382(15)
C3 N2 1.3636(15)
C3 C5 1.4522(16)
C4 N2 1.4721(15)
C4 H4A 0.9800
C4 H4B 0.9800
C4 H4C 0.9800
C5 N3 1.2731(15)
C5 H5 0.9500
C6 O1 1.4393(13)
C6 C7 1.5013(16)
C6 H6A 0.9900
C6 H6B 0.9900
C7 C12 1.3890(16)
C7 C8 1.4005(17)
C8 C9 1.3890(17)
C8 H8 0.9500
C9 C10 1.3757(18)
C9 H9 0.9500
C10 F1 1.3679(14)
C10 C11 1.3791(19)
C11 C12 1.3888(17)
C11 H11 0.9500
C12 H12 0.9500
N3 O1 1.4012(12)
N4 O2 1.2301(14)
N4 O3 1.2339(14)
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
C4 H4C N3 . 0.98 2.29 3.0184(15) 131
C4 H4A N1 2 0.98 2.63 3.5693(16) 160
C9 H9 N1 4_566 0.95 2.58 3.4973(16) 163
C2 H2 O3 3_665 0.95 2.49 3.3165(15) 145
C5 H5 O2 2_545 0.95 2.63 3.1676(14) 116
C6 H6A O2 4_576 0.99 2.54 3.1376(14) 119
C4 H4C F1 2_556 0.98 2.77 3.353(2) 119
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
N2 C1 C2 N1 -0.16(13)
N4 C1 C2 N1 -179.62(11)
N1 C3 C5 N3 -162.10(10)
N2 C3 C5 N3 17.64(18)
O1 C6 C7 C12 152.70(10)
O1 C6 C7 C8 -30.95(14)
C12 C7 C8 C9 0.13(16)
C6 C7 C8 C9 -176.23(10)
C7 C8 C9 C10 0.82(17)
C8 C9 C10 F1 178.37(10)
C8 C9 C10 C11 -0.87(18)
F1 C10 C11 C12 -179.30(10)
C9 C10 C11 C12 -0.05(18)
C10 C11 C12 C7 1.06(18)
C8 C7 C12 C11 -1.10(17)
C6 C7 C12 C11 175.34(10)
N2 C3 N1 C2 -1.05(13)
C5 C3 N1 C2 178.73(10)
C1 C2 N1 C3 0.72(13)
N1 C3 N2 C1 0.95(12)
C5 C3 N2 C1 -178.81(11)
N1 C3 N2 C4 -172.71(10)
C5 C3 N2 C4 7.53(18)
C2 C1 N2 C3 -0.46(12)
N4 C1 N2 C3 179.02(10)
C2 C1 N2 C4 173.07(10)
N4 C1 N2 C4 -7.45(18)
C3 C5 N3 O1 179.79(9)
C2 C1 N4 O2 -178.34(11)
N2 C1 N4 O2 2.29(17)
C2 C1 N4 O3 2.41(18)
N2 C1 N4 O3 -176.96(11)
C5 N3 O1 C6 -173.96(9)
C7 C6 O1 N3 175.61(8)

_cod_database_fobs_code 2242395
