#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/88/2228868.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_2228868
loop_
_publ_author_name
'Wu, Hong-Yun'
'Ban, Hong-Yan'
'Wang, Jia-Bo'
'Zhang, Li-Hua'
_publ_section_title
;
 (E)-2-Fluoro-N'-(4-nitrobenzylidene)benzohydrazide
;
_journal_coeditor_code           RZ2538
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o160
_journal_paper_doi               10.1107/S1600536810052268
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C14 H10 F N3 O3'
_chemical_formula_moiety         'C14 H10 F N3 O3'
_chemical_formula_sum            'C14 H10 F N3 O3'
_chemical_formula_weight         287.25
_chemical_name_systematic
;
(E)-2-Fluoro-N'-(4-nitrobenzylidene)benzohydrazide
;
_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                 111.640(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.077(2)
_cell_length_b                   25.718(4)
_cell_length_c                   7.6844(17)
_cell_measurement_reflns_used    680
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.5
_cell_measurement_theta_min      2.5
_cell_volume                     1300.0(5)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       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  0.0740
_diffrn_reflns_av_sigmaI/netI    0.1181
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            6999
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.96
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.9829
_exptl_absorpt_correction_T_min  0.9806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.221
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2810
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.981
_refine_ls_R_factor_all          0.1841
_refine_ls_R_factor_gt           0.0672
_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)+(0.0571P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1266
_refine_ls_wR_factor_ref         0.1731
_reflns_number_gt                1155
_reflns_number_total             2810
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2538.cif
_cod_data_source_block           I
_cod_original_cell_volume        1300.1(5)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2228868
_cod_database_fobs_code          2228868
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_disorder_assembly
_atom_site_disorder_group
F F1 0.2225(4) 0.24829(9) 0.4967(3) 0.0822(8) Uani d . 1 . .
N N1 0.2495(5) 0.48648(15) -0.5057(5) 0.0631(10) Uani d . 1 . .
N N2 0.2488(4) 0.29033(11) 0.0113(4) 0.0432(8) Uani d . 1 . .
N N3 0.2828(5) 0.25789(11) 0.1631(4) 0.0464(8) Uani d D 1 . .
O O1 0.2201(5) 0.47230(12) -0.6636(4) 0.0978(12) Uani d . 1 . .
O O2 0.2646(6) 0.53203(12) -0.4634(5) 0.1069(13) Uani d . 1 . .
O O3 0.0937(4) 0.19271(9) -0.0144(3) 0.0547(8) Uani d . 1 . .
C C1 0.2637(5) 0.44701(14) -0.3635(5) 0.0438(9) Uani d . 1 . .
C C2 0.2406(6) 0.39574(14) -0.4128(5) 0.0486(10) Uani d . 1 . .
H H2 0.2183 0.3855 -0.5348 0.058 Uiso calc R 1 . .
C C3 0.2511(5) 0.35963(14) -0.2776(5) 0.0465(10) Uani d . 1 . .
H H3 0.2325 0.3246 -0.3094 0.056 Uiso calc R 1 . .
C C4 0.2891(5) 0.37471(13) -0.0952(5) 0.0374(8) Uani d . 1 . .
C C5 0.3140(5) 0.42716(14) -0.0505(5) 0.0474(10) Uani d . 1 . .
H H5 0.3419 0.4376 0.0723 0.057 Uiso calc R 1 . .
C C6 0.2981(5) 0.46400(13) -0.1853(5) 0.0494(10) Uani d . 1 . .
H H6 0.3103 0.4993 -0.1564 0.059 Uiso calc R 1 . .
C C7 0.3085(5) 0.33691(14) 0.0518(5) 0.0448(10) Uani d . 1 . .
H H7 0.3652 0.3470 0.1766 0.054 Uiso calc R 1 . .
C C8 0.2013(5) 0.21010(13) 0.1394(5) 0.0404(9) Uani d . 1 . .
C C9 0.2475(5) 0.17828(13) 0.3115(5) 0.0361(8) Uani d . 1 . .
C C10 0.2603(5) 0.19735(14) 0.4817(5) 0.0484(10) Uani d . 1 . .
C C11 0.3020(6) 0.16713(18) 0.6393(5) 0.0627(12) Uani d . 1 . .
H H11 0.3100 0.1815 0.7529 0.075 Uiso calc R 1 . .
C C12 0.3310(6) 0.11534(18) 0.6222(6) 0.0658(12) Uani d . 1 . .
H H12 0.3597 0.0940 0.7266 0.079 Uiso calc R 1 . .
C C13 0.3190(5) 0.09383(15) 0.4558(6) 0.0595(11) Uani d . 1 . .
H H13 0.3399 0.0584 0.4478 0.071 Uiso calc R 1 . .
C C14 0.2757(5) 0.12515(13) 0.2996(6) 0.0489(10) Uani d . 1 . .
H H14 0.2653 0.1105 0.1858 0.059 Uiso calc R 1 . .
H H3A 0.374(4) 0.2695(13) 0.272(3) 0.073 Uiso d 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 N1 O1 . . 121.8(4) ?
O2 N1 C1 . . 119.7(4) ?
O1 N1 C1 . . 118.5(4) ?
C7 N2 N3 . . 115.1(3) ?
C8 N3 N2 . . 120.4(3) ?
C8 N3 H3A . . 124(2) ?
N2 N3 H3A . . 115(2) ?
C2 C1 C6 . . 123.0(3) ?
C2 C1 N1 . . 119.6(3) ?
C6 C1 N1 . . 117.5(3) ?
C1 C2 C3 . . 118.4(3) ?
C1 C2 H2 . . 120.8 ?
C3 C2 H2 . . 120.8 ?
C2 C3 C4 . . 120.8(3) ?
C2 C3 H3 . . 119.6 ?
C4 C3 H3 . . 119.6 ?
C3 C4 C5 . . 118.9(3) ?
C3 C4 C7 . . 121.7(3) ?
C5 C4 C7 . . 119.3(3) ?
C6 C5 C4 . . 121.0(3) ?
C6 C5 H5 . . 119.5 ?
C4 C5 H5 . . 119.5 ?
C1 C6 C5 . . 117.8(3) ?
C1 C6 H6 . . 121.1 ?
C5 C6 H6 . . 121.1 ?
N2 C7 C4 . . 120.8(3) ?
N2 C7 H7 . . 119.6 ?
C4 C7 H7 . . 119.6 ?
O3 C8 N3 . . 123.1(3) ?
O3 C8 C9 . . 120.7(3) ?
N3 C8 C9 . . 116.2(3) ?
C10 C9 C14 . . 117.1(3) ?
C10 C9 C8 . . 124.7(3) ?
C14 C9 C8 . . 118.3(3) ?
F1 C10 C9 . . 118.9(3) ?
F1 C10 C11 . . 117.3(4) ?
C9 C10 C11 . . 123.8(4) ?
C12 C11 C10 . . 117.3(4) ?
C12 C11 H11 . . 121.3 ?
C10 C11 H11 . . 121.3 ?
C11 C12 C13 . . 121.8(4) ?
C11 C12 H12 . . 119.1 ?
C13 C12 H12 . . 119.1 ?
C12 C13 C14 . . 119.6(4) ?
C12 C13 H13 . . 120.2 ?
C14 C13 H13 . . 120.2 ?
C13 C14 C9 . . 120.5(4) ?
C13 C14 H14 . . 119.8 ?
C9 C14 H14 . . 119.8 ?
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
F1 C10 . 1.350(4) ?
N1 O2 . 1.210(4) ?
N1 O1 . 1.210(4) ?
N1 C1 . 1.468(5) ?
N2 C7 . 1.270(4) ?
N2 N3 . 1.381(4) ?
N3 C8 . 1.341(4) ?
N3 H3A . 0.900(10) ?
O3 C8 . 1.230(4) ?
C1 C2 . 1.365(4) ?
C1 C6 . 1.370(4) ?
C2 C3 . 1.375(5) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.382(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.387(4) ?
C4 C7 . 1.458(5) ?
C5 C6 . 1.377(5) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.485(4) ?
C9 C10 . 1.368(4) ?
C9 C14 . 1.389(4) ?
C10 C11 . 1.376(5) ?
C11 C12 . 1.361(5) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.367(5) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.383(5) ?
C13 H13 . 0.9300 ?
C14 H14 . 0.9300 ?
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
N3 H3A O3 4_666 0.900(10) 2.04(3) 2.928(3) 168(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 5287085
