#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/96/2219669.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_2219669
loop_
_publ_author_name
'Feng, Hai-Mei'
'Wang, Xin'
'Lei, Ke-Wei'
_publ_section_title
;
 N-(4-Fluorobenzoyl)-2-hydroxy-4-methylbenzohydrazide
;
_journal_coeditor_code           NG2492
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1953
_journal_paper_doi               10.1107/S1600536808029292
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C15 H13 F N2 O3'
_chemical_formula_moiety         'C15 H13 F N2 O3'
_chemical_formula_sum            'C15 H13 F N2 O3'
_chemical_formula_weight         288.27
_chemical_melting_point_gt       490
_chemical_melting_point_lt       499
_chemical_name_systematic
;
N-(4-Fluorobenzoyl)-2-hydroxy-4-methylbenzohydrazide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                102.854(2)
_cell_angle_beta                 97.754(3)
_cell_angle_gamma                105.5380(10)
_cell_formula_units_Z            2
_cell_length_a                   7.0969(13)
_cell_length_b                   7.2994(14)
_cell_length_c                   13.701(3)
_cell_measurement_reflns_used    6530
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.62
_cell_measurement_theta_min      1.56
_cell_volume                     652.2(2)
_computing_cell_refinement       'APEX2 (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_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      296(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker Kappa APEXII diffractometer'
_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  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0275
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4591
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.56
_diffrn_standards_decay_%        no
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.540
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.446
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2274
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0467
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0930P)²+0.2642P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1338
_refine_ls_wR_factor_ref         0.1393
_reflns_number_gt                2090
_reflns_number_total             2274
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ng2492.cif
_cod_data_source_block           I
_cod_database_code               2219669
_cod_database_fobs_code          2219669
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C C1 1.5146(3) 0.7327(3) 0.90895(14) 0.0382(4) Uani d . 1
H H1A 1.5688 0.6263 0.9116 0.057 Uiso calc R 1
H H1B 1.4846 0.7824 0.9741 0.057 Uiso calc R 1
H H1C 1.6105 0.8366 0.8931 0.057 Uiso calc R 1
C C2 1.3255(2) 0.6585(2) 0.82719(12) 0.0275(4) Uani d . 1
C C3 1.1619(2) 0.7274(2) 0.83934(12) 0.0291(4) Uani d . 1
H H3A 1.1679 0.8211 0.8990 0.035 Uiso calc R 1
C C4 0.9911(2) 0.6566(2) 0.76276(12) 0.0256(4) Uani d . 1
H H4A 0.8839 0.7043 0.7722 0.031 Uiso calc R 1
C C5 1.3107(2) 0.5166(2) 0.73751(12) 0.0260(4) Uani d . 1
H H5A 1.4184 0.4696 0.7285 0.031 Uiso calc R 1
C C6 1.1384(2) 0.4435(2) 0.66103(11) 0.0227(3) Uani d . 1
C C7 0.9748(2) 0.5153(2) 0.67156(11) 0.0215(3) Uani d . 1
C C8 0.7818(2) 0.4502(2) 0.59554(11) 0.0210(3) Uani d . 1
C C9 0.5611(2) 0.0444(2) 0.37524(11) 0.0225(3) Uani d . 1
C C10 0.3744(2) -0.0450(2) 0.29516(12) 0.0228(4) Uani d . 1
C C11 0.3805(2) -0.1729(2) 0.20387(12) 0.0292(4) Uani d . 1
H H11A 0.4995 -0.1983 0.1948 0.035 Uiso calc R 1
C C12 0.1944(2) -0.0106(2) 0.30968(12) 0.0258(4) Uani d . 1
H H12A 0.1892 0.0725 0.3708 0.031 Uiso calc R 1
C C13 0.0234(2) -0.1002(2) 0.23314(13) 0.0298(4) Uani d . 1
H H13A -0.0972 -0.0786 0.2422 0.036 Uiso calc R 1
C C14 0.2107(3) -0.2622(3) 0.12657(13) 0.0332(4) Uani d . 1
H H14A 0.2140 -0.3465 0.0654 0.040 Uiso calc R 1
C C15 0.0363(2) -0.2216(2) 0.14356(13) 0.0311(4) Uani d . 1
F F -0.13083(16) -0.30700(16) 0.06798(8) 0.0459(3) Uani d . 1
N N1 0.76066(18) 0.30055(19) 0.51310(10) 0.0239(3) Uani d . 1
H H1D 0.8590 0.2550 0.5049 0.029 Uiso calc R 1
N N2 0.58263(18) 0.21862(18) 0.44102(9) 0.0223(3) Uani d . 1
H H2A 0.4916 0.2760 0.4386 0.027 Uiso calc R 1
O O1 1.12712(16) 0.30064(17) 0.57426(8) 0.0287(3) Uani d . 1
H H1E 1.1820 0.2223 0.5895 0.043 Uiso calc R 1
O O2 0.64816(15) 0.52694(16) 0.60736(8) 0.0270(3) Uani d . 1
O O3 0.69450(16) -0.03614(17) 0.38199(9) 0.0320(3) 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
_geom_angle_publ_flag
C2 C1 H1A 109.5 ?
C2 C1 H1B 109.5 ?
H1A C1 H1B 109.5 ?
C2 C1 H1C 109.5 ?
H1A C1 H1C 109.5 ?
H1B C1 H1C 109.5 ?
C5 C2 C3 118.40(14) ?
C5 C2 C1 119.88(15) ?
C3 C2 C1 121.71(15) ?
C4 C3 C2 120.21(14) ?
C4 C3 H3A 119.9 ?
C2 C3 H3A 119.9 ?
C3 C4 C7 122.03(14) ?
C3 C4 H4A 119.0 ?
C7 C4 H4A 119.0 ?
C2 C5 C6 121.48(14) ?
C2 C5 H5A 119.3 ?
C6 C5 H5A 119.3 ?
O1 C6 C5 120.01(13) y
O1 C6 C7 119.48(13) y
C5 C6 C7 120.50(14) ?
C4 C7 C6 117.33(14) ?
C4 C7 C8 116.67(13) ?
C6 C7 C8 125.97(14) ?
O2 C8 N1 121.54(13) y
O2 C8 C7 122.52(13) y
N1 C8 C7 115.94(12) y
O3 C9 N2 120.31(14) y
O3 C9 C10 122.26(13) y
N2 C9 C10 117.42(12) y
C12 C10 C11 119.65(14) ?
C12 C10 C9 122.36(14) ?
C11 C10 C9 117.95(13) ?
C14 C11 C10 120.64(15) ?
C14 C11 H11A 119.7 ?
C10 C11 H11A 119.7 ?
C13 C12 C10 120.17(15) ?
C13 C12 H12A 119.9 ?
C10 C12 H12A 119.9 ?
C15 C13 C12 118.47(15) ?
C15 C13 H13A 120.8 ?
C12 C13 H13A 120.8 ?
C15 C14 C11 117.78(15) ?
C15 C14 H14A 121.1 ?
C11 C14 H14A 121.1 ?
F C15 C13 118.40(15) ?
F C15 C14 118.34(15) ?
C13 C15 C14 123.26(15) ?
C8 N1 N2 121.02(12) ?
C8 N1 H1D 119.5 ?
N2 N1 H1D 119.5 ?
C9 N2 N1 115.98(12) ?
C9 N2 H2A 122.0 ?
N1 N2 H2A 122.0 ?
C6 O1 H1E 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.511(2)
C1 H1A 0.9601
C1 H1B 0.9601
C1 H1C 0.9601
C2 C5 1.390(2)
C2 C3 1.399(2)
C3 C4 1.385(2)
C3 H3A 0.9300
C4 C7 1.401(2)
C4 H4A 0.9300
C5 C6 1.391(2)
C5 H5A 0.9300
C6 O1 1.3732(19)
C6 C7 1.407(2)
C7 C8 1.494(2)
C8 O2 1.2351(18)
C8 N1 1.345(2)
C9 O3 1.2451(19)
C9 N2 1.342(2)
C9 C10 1.487(2)
C10 C12 1.397(2)
C10 C11 1.398(2)
C11 C14 1.388(2)
C11 H11A 0.9300
C12 C13 1.388(2)
C12 H12A 0.9300
C13 C15 1.375(3)
C13 H13A 0.9300
C14 C15 1.385(3)
C14 H14A 0.9300
C15 F 1.3614(18)
N1 N2 1.3875(17)
N1 H1D 0.8600
N2 H2A 0.8600
O1 H1E 0.8200
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
_geom_hbond_publ_flag
N1 H1D O1 1_555 0.8597 1.9148 2.6224(19) 138.64 y
O1 H1E O3 2_756 0.8202 1.8839 2.7035(18) 177.34 y
N2 H2A O2 2_666 0.8598 2.1091 2.9079(19) 154.32 y
C4 H4A O2 1_555 0.9302 2.4688 2.797(2) 100.84 n
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24740769
