#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/39/2233986.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_2233986
loop_
_publ_author_name
'Li, Xiao-Yan'
_publ_section_title
;
 (E)-N'-(3-Fluorobenzylidene)-3-nitrobenzohydrazide
;
_journal_coeditor_code           RZ2708
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o697
_journal_paper_doi               10.1107/S1600536812005478
_journal_volume                  68
_journal_year                    2012
_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)-N'-(3-Fluorobenzylidene)-3-nitrobenzohydrazide
;
_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'
_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                 94.855(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.823(2)
_cell_length_b                   12.813(3)
_cell_length_c                   8.7020(17)
_cell_measurement_reflns_used    690
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.20
_cell_measurement_theta_min      2.35
_cell_volume                     1313.5(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 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'ω scans'
_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  0.0745
_diffrn_reflns_av_sigmaI/netI    0.0850
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9452
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.73
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  0.9831
_exptl_absorpt_correction_T_min  0.9808
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.453
_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          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.588
_refine_diff_density_min         -0.224
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2429
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.1352
_refine_ls_R_factor_gt           0.0798
_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)+(0.0985P)²+0.4222P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1867
_refine_ls_wR_factor_ref         0.2179
_reflns_number_gt                1438
_reflns_number_total             2429
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2708.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2233986
_cod_database_fobs_code          2233986
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_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
F F1 0.6421(4) -0.2974(2) 1.1301(4) 0.1160(14) Uani d . 1 1
N N1 1.0252(3) 0.4021(4) 0.6545(5) 0.0679(12) Uani d . 1 1
N N2 0.7281(3) 0.2345(2) 0.9891(3) 0.0395(8) Uani d D 1 1
N N3 0.6810(3) 0.1600(2) 1.0796(3) 0.0378(8) Uani d . 1 1
O O1 1.0149(4) 0.3120(3) 0.6079(6) 0.1118(16) Uani d . 1 1
O O2 1.0930(3) 0.4628(3) 0.6109(4) 0.0929(13) Uani d . 1 1
O O3 0.7513(2) 0.34723(19) 1.1894(3) 0.0479(8) Uani d . 1 1
C C1 0.8197(3) 0.3996(3) 0.9543(4) 0.0342(9) Uani d . 1 1
C C2 0.8882(3) 0.3651(3) 0.8433(4) 0.0375(9) Uani d . 1 1
H H2A 0.8947 0.2943 0.8222 0.045 Uiso calc R 1 1
C C3 0.9466(3) 0.4386(3) 0.7646(4) 0.0427(10) Uani d . 1 1
C C4 0.9357(4) 0.5431(3) 0.7881(5) 0.0527(11) Uani d . 1 1
H H4 0.9744 0.5910 0.7318 0.063 Uiso calc R 1 1
C C5 0.8655(4) 0.5763(3) 0.8979(5) 0.0538(11) Uani d . 1 1
H H5 0.8568 0.6473 0.9156 0.065 Uiso calc R 1 1
C C6 0.8089(3) 0.5051(3) 0.9806(5) 0.0445(10) Uani d . 1 1
H H6 0.7628 0.5282 1.0551 0.053 Uiso calc R 1 1
C C7 0.7631(3) 0.3250(3) 1.0550(4) 0.0354(9) Uani d . 1 1
C C8 0.6781(3) 0.0680(3) 1.0258(4) 0.0367(9) Uani d . 1 1
H H8 0.7070 0.0547 0.9316 0.044 Uiso calc R 1 1
C C9 0.6300(3) -0.0173(3) 1.1103(4) 0.0385(9) Uani d . 1 1
C C10 0.6562(4) -0.1197(3) 1.0745(5) 0.0529(11) Uani d . 1 1
H H10 0.7025 -0.1344 0.9961 0.064 Uiso calc R 1 1
C C11 0.6121(4) -0.1984(3) 1.1575(5) 0.0619(13) Uani d . 1 1
C C12 0.5428(4) -0.1806(4) 1.2734(5) 0.0634(13) Uani d . 1 1
H H12 0.5138 -0.2358 1.3273 0.076 Uiso calc R 1 1
C C13 0.5176(4) -0.0806(4) 1.3071(5) 0.0546(12) Uani d . 1 1
H H13 0.4702 -0.0673 1.3848 0.066 Uiso calc R 1 1
C C14 0.5605(3) 0.0019(3) 1.2291(4) 0.0447(10) Uani d . 1 1
H H14 0.5433 0.0701 1.2555 0.054 Uiso calc R 1 1
H H2 0.736(4) 0.215(4) 0.891(2) 0.080 Uiso d D 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'
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
O2 N1 O1 123.8(4)
O2 N1 C3 118.4(4)
O1 N1 C3 117.8(4)
C7 N2 N3 118.5(3)
C7 N2 H2 126(3)
N3 N2 H2 115(3)
C8 N3 N2 115.5(3)
C6 C1 C2 119.8(3)
C6 C1 C7 118.6(3)
C2 C1 C7 121.5(3)
C3 C2 C1 118.3(4)
C3 C2 H2A 120.9
C1 C2 H2A 120.9
C4 C3 C2 122.5(4)
C4 C3 N1 119.0(4)
C2 C3 N1 118.5(4)
C3 C4 C5 118.4(4)
C3 C4 H4 120.8
C5 C4 H4 120.8
C6 C5 C4 120.4(4)
C6 C5 H5 119.8
C4 C5 H5 119.8
C5 C6 C1 120.6(4)
C5 C6 H6 119.7
C1 C6 H6 119.7
O3 C7 N2 123.6(3)
O3 C7 C1 120.3(3)
N2 C7 C1 116.0(3)
N3 C8 C9 120.6(3)
N3 C8 H8 119.7
C9 C8 H8 119.7
C10 C9 C14 119.2(4)
C10 C9 C8 119.4(3)
C14 C9 C8 121.4(3)
C11 C10 C9 118.4(4)
C11 C10 H10 120.8
C9 C10 H10 120.8
F1 C11 C10 118.9(5)
F1 C11 C12 118.1(4)
C10 C11 C12 122.9(4)
C13 C12 C11 118.2(4)
C13 C12 H12 120.9
C11 C12 H12 120.9
C12 C13 C14 121.6(4)
C12 C13 H13 119.2
C14 C13 H13 119.2
C13 C14 C9 119.7(4)
C13 C14 H14 120.2
C9 C14 H14 120.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C11 1.344(5)
N1 O2 1.201(5)
N1 O1 1.225(5)
N1 C3 1.467(5)
N2 C7 1.343(5)
N2 N3 1.383(4)
N2 H2 0.897(10)
N3 C8 1.268(4)
O3 C7 1.223(4)
C1 C6 1.379(5)
C1 C2 1.384(5)
C1 C7 1.493(5)
C2 C3 1.384(5)
C2 H2A 0.9300
C3 C4 1.362(6)
C4 C5 1.384(6)
C4 H4 0.9300
C5 C6 1.372(6)
C5 H5 0.9300
C6 H6 0.9300
C8 C9 1.459(5)
C8 H8 0.9300
C9 C10 1.390(6)
C9 C14 1.396(5)
C10 C11 1.369(6)
C10 H10 0.9300
C11 C12 1.371(7)
C12 C13 1.353(6)
C12 H12 0.9300
C13 C14 1.376(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
N2 H2 O3 4_565 0.897(10) 1.955(13) 2.846(4) 172(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 7839575
