#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/13/2221317.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_2221317
loop_
_publ_author_name
'Liu, Deyun'
_publ_section_title
;
 N'-Cyclohexylidene-2-hydroxybenzohydrazide
;
_journal_coeditor_code           CV2521
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o691
_journal_paper_doi               10.1107/S1600536809007636
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C13 H16 N2 O2'
_chemical_formula_moiety         'C13 H16 N2 O2'
_chemical_formula_sum            'C13 H16 N2 O2'
_chemical_formula_weight         232.28
_chemical_name_systematic        ?
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 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                 102.241(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.376(2)
_cell_length_b                   5.3386(10)
_cell_length_c                   12.9435(15)
_cell_measurement_reflns_used    1322
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.498
_cell_measurement_theta_min      3.221
_cell_volume                     1240.9(3)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART Apex CCD area-detector'
_diffrn_measurement_method       'phi and omega 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  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0271
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2969
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.27
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9774
_exptl_absorpt_correction_T_min  0.9676
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.150
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1090
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0465
_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)+(0.0866P)²+0.3353P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1265
_refine_ls_wR_factor_ref         0.1377
_reflns_number_gt                898
_reflns_number_total             1090
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cv2521.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               2221317
_cod_database_fobs_code          2221317
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, 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
N N1 0.18964(17) 0.6052(6) 0.1521(2) 0.0432(8) Uani d . 1 . .
H H1 0.1776 0.6179 0.2126 0.052 Uiso calc R 1 . .
N N2 0.15740(18) 0.7600(7) 0.0684(2) 0.0475(8) Uani d . 1 . .
O O1 0.2584(2) 0.4124(5) 0.0501(2) 0.0577(8) Uani d . 1 . .
O O2 0.20359(16) 0.4399(5) 0.3488(2) 0.0511(8) Uani d . 1 . .
H H2 0.1965 0.4152 0.4084 0.077 Uiso calc R 1 . .
C C1 0.24015(19) 0.4354(7) 0.1362(2) 0.0371(8) Uani d . 1 . .
C C2 0.27283(19) 0.2675(7) 0.2264(3) 0.0369(8) Uani d . 1 . .
C C3 0.25343(18) 0.2669(6) 0.3267(3) 0.0370(8) Uani d . 1 . .
C C4 0.2836(2) 0.0878(7) 0.4024(3) 0.0465(10) Uani d . 1 . .
H H4 0.2699 0.0859 0.4675 0.056 Uiso calc R 1 . .
C C5 0.3333(2) -0.0845(8) 0.3810(3) 0.0524(11) Uani d . 1 . .
H H5 0.3533 -0.2032 0.4317 0.063 Uiso calc R 1 . .
C C6 0.3545(2) -0.0838(7) 0.2838(3) 0.0505(11) Uani d . 1 . .
H H6 0.3890 -0.1997 0.2699 0.061 Uiso calc R 1 . .
C C7 0.3240(2) 0.0891(7) 0.2088(3) 0.0422(9) Uani d . 1 . .
H H7 0.3380 0.0871 0.1439 0.051 Uiso calc R 1 . .
C C8 0.1097(3) 0.9202(8) 0.0854(3) 0.0531(11) Uani d . 1 . .
C C9 0.0802(3) 0.9560(10) 0.1848(4) 0.0681(13) Uani d . 1 . .
H H9A 0.0993 0.8241 0.2348 0.082 Uiso calc R 1 . .
H H9B 0.0976 1.1151 0.2170 0.082 Uiso calc R 1 . .
C C10 -0.0029(3) 0.9511(13) 0.1616(5) 0.0863(18) Uani d . 1 . .
H H10A -0.0200 0.9941 0.2253 0.104 Uiso calc R 1 . .
H H10B -0.0198 0.7824 0.1415 0.104 Uiso calc R 1 . .
C C11 -0.0380(3) 1.1323(12) 0.0730(5) 0.0874(17) Uani d . 1 . .
H H11A -0.0917 1.1123 0.0572 0.105 Uiso calc R 1 . .
H H11B -0.0266 1.3034 0.0961 0.105 Uiso calc R 1 . .
C C12 -0.0081(3) 1.0816(13) -0.0264(5) 0.0849(17) Uani d . 1 . .
H H12A -0.0253 0.9184 -0.0543 0.102 Uiso calc R 1 . .
H H12B -0.0280 1.2059 -0.0795 0.102 Uiso calc R 1 . .
C C13 0.0746(3) 1.0884(9) -0.0060(4) 0.0690(14) Uani d . 1 . .
H H13A 0.0914 1.2591 0.0096 0.083 Uiso calc R 1 . .
H H13B 0.0908 1.0354 -0.0691 0.083 Uiso calc R 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
C1 N1 N2 . . 118.4(3) ?
C1 N1 H1 . . 120.8 ?
N2 N1 H1 . . 120.8 ?
C8 N2 N1 . . 117.3(3) ?
C3 O2 H2 . . 109.5 ?
O1 C1 N1 . . 122.2(3) ?
O1 C1 C2 . . 120.3(3) ?
N1 C1 C2 . . 117.5(3) ?
C7 C2 C3 . . 117.3(3) ?
C7 C2 C1 . . 117.2(3) ?
C3 C2 C1 . . 125.4(3) ?
O2 C3 C4 . . 119.8(3) ?
O2 C3 C2 . . 119.9(3) ?
C4 C3 C2 . . 120.3(3) ?
C5 C4 C3 . . 120.1(4) ?
C5 C4 H4 . . 119.9 ?
C3 C4 H4 . . 119.9 ?
C4 C5 C6 . . 120.5(4) ?
C4 C5 H5 . . 119.7 ?
C6 C5 H5 . . 119.7 ?
C7 C6 C5 . . 119.4(4) ?
C7 C6 H6 . . 120.3 ?
C5 C6 H6 . . 120.3 ?
C6 C7 C2 . . 122.3(4) ?
C6 C7 H7 . . 118.8 ?
C2 C7 H7 . . 118.8 ?
N2 C8 C9 . . 128.0(4) ?
N2 C8 C13 . . 117.1(4) ?
C9 C8 C13 . . 114.8(4) ?
C10 C9 C8 . . 111.3(4) ?
C10 C9 H9A . . 109.4 ?
C8 C9 H9A . . 109.4 ?
C10 C9 H9B . . 109.4 ?
C8 C9 H9B . . 109.4 ?
H9A C9 H9B . . 108.0 ?
C9 C10 C11 . . 112.9(5) ?
C9 C10 H10A . . 109.0 ?
C11 C10 H10A . . 109.0 ?
C9 C10 H10B . . 109.0 ?
C11 C10 H10B . . 109.0 ?
H10A C10 H10B . . 107.8 ?
C12 C11 C10 . . 110.4(5) ?
C12 C11 H11A . . 109.6 ?
C10 C11 H11A . . 109.6 ?
C12 C11 H11B . . 109.6 ?
C10 C11 H11B . . 109.6 ?
H11A C11 H11B . . 108.1 ?
C13 C12 C11 . . 112.5(5) ?
C13 C12 H12A . . 109.1 ?
C11 C12 H12A . . 109.1 ?
C13 C12 H12B . . 109.1 ?
C11 C12 H12B . . 109.1 ?
H12A C12 H12B . . 107.8 ?
C12 C13 C8 . . 112.0(5) ?
C12 C13 H13A . . 109.2 ?
C8 C13 H13A . . 109.2 ?
C12 C13 H13B . . 109.2 ?
C8 C13 H13B . . 109.2 ?
H13A C13 H13B . . 107.9 ?
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
N1 C1 . 1.344(5) ?
N1 N2 . 1.391(4) ?
N1 H1 . 0.8600 ?
N2 C8 . 1.277(5) ?
O1 C1 . 1.236(5) ?
O2 C3 . 1.373(4) ?
O2 H2 . 0.8200 ?
C1 C2 . 1.493(5) ?
C2 C7 . 1.391(5) ?
C2 C3 . 1.417(4) ?
C3 C4 . 1.398(5) ?
C4 C5 . 1.365(6) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.394(6) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.370(6) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.510(6) ?
C8 C13 . 1.516(6) ?
C9 C10 . 1.493(8) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 C11 . 1.534(9) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C12 . 1.526(9) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 C13 . 1.486(8) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
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
N1 H1 O2 . 0.86 1.97 2.655(4) 135.7
O2 H2 O1 2_565 0.82 2.15 2.704(4) 125.0
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 594616
