#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/18/2221866.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_2221866
loop_
_publ_author_name
'Lo, Kong Mun'
'Ng, Seik Weng'
_publ_section_title
;
 4-Hydroxy-N'-(4-hydroxybenzoyl)benzohydrazide
;
_journal_coeditor_code           XU2507
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o969
_journal_paper_doi               10.1107/S1600536809012136
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H12 N2 O4'
_chemical_formula_moiety         'C14 H12 N2 O4'
_chemical_formula_sum            'C14 H12 N2 O4'
_chemical_formula_weight         272.26
_chemical_name_systematic
;
4-Hydroxy-N'-(4-hydroxybenzoyl)benzohydrazide
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.7058(7)
_cell_length_b                   9.7646(8)
_cell_length_c                   14.2580(10)
_cell_measurement_reflns_used    3150
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      28.1
_cell_measurement_theta_min      2.7
_cell_volume                     1212.05(16)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type  'Bruker SMART APEX'
_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  0.0213
_diffrn_reflns_av_sigmaI/netI    0.0188
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6928
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.53
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'Light yellow'
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.170
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         1599
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0304
_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)+(0.0567P)²+0.1781P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0839
_refine_ls_wR_factor_ref         0.0875
_reflns_number_gt                1475
_reflns_number_total             1599
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2507.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' 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 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' 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_database_code               2221866
_cod_database_fobs_code          2221866
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.60946(17) 0.59285(14) 0.90517(8) 0.0287(3) Uani d D 1 . .
O O2 0.72656(15) 0.62247(13) 0.46567(8) 0.0247(3) Uani d . 1 . .
O O3 0.65093(19) 0.92446(15) 0.39648(9) 0.0364(4) Uani d . 1 . .
O O4 0.63007(17) 0.90074(14) -0.04878(8) 0.0310(3) Uani d D 1 . .
N N1 0.49389(17) 0.72003(15) 0.47376(9) 0.0217(3) Uani d D 1 . .
N N2 0.49553(19) 0.74438(15) 0.37802(9) 0.0223(3) Uani d D 1 . .
C C1 0.6163(2) 0.60858(17) 0.81114(11) 0.0206(3) Uani d . 1 . .
C C2 0.7010(2) 0.52136(18) 0.75329(12) 0.0224(4) Uani d . 1 . .
H H2 0.7591 0.4487 0.7799 0.027 Uiso calc R 1 . .
C C3 0.7002(2) 0.54091(17) 0.65708(12) 0.0222(4) Uani d . 1 . .
H H3 0.7585 0.4818 0.6179 0.027 Uiso calc R 1 . .
C C4 0.61465(19) 0.64672(17) 0.61727(11) 0.0191(3) Uani d . 1 . .
C C5 0.5318(2) 0.73400(18) 0.67564(11) 0.0214(3) Uani d . 1 . .
H H5 0.4735 0.8065 0.6491 0.026 Uiso calc R 1 . .
C C6 0.5334(2) 0.71626(18) 0.77205(11) 0.0235(4) Uani d . 1 . .
H H6 0.4781 0.7774 0.8114 0.028 Uiso calc R 1 . .
C C7 0.6172(2) 0.66161(17) 0.51417(11) 0.0197(3) Uani d . 1 . .
C C8 0.5846(2) 0.84605(18) 0.34327(12) 0.0226(4) Uani d . 1 . .
C C9 0.5944(2) 0.85689(17) 0.23956(12) 0.0210(4) Uani d . 1 . .
C C10 0.7023(2) 0.94658(17) 0.20197(12) 0.0224(4) Uani d . 1 . .
H H10 0.7664 0.9979 0.2429 0.027 Uiso calc R 1 . .
C C11 0.7180(2) 0.96226(18) 0.10568(12) 0.0233(4) Uani d . 1 . .
H H11 0.7928 1.0232 0.0809 0.028 Uiso calc R 1 . .
C C12 0.6230(2) 0.88771(17) 0.04537(11) 0.0222(4) Uani d . 1 . .
C C13 0.5156(2) 0.79694(19) 0.08191(11) 0.0265(4) Uani d . 1 . .
H H13 0.4517 0.7455 0.0409 0.032 Uiso calc R 1 . .
C C14 0.5017(2) 0.78146(18) 0.17811(12) 0.0247(4) Uani d . 1 . .
H H14 0.4285 0.7189 0.2027 0.030 Uiso calc R 1 . .
H H1O 0.668(3) 0.529(2) 0.9222(17) 0.045(7) Uiso d D 1 . .
H H4O 0.698(2) 0.958(2) -0.0659(18) 0.050(8) Uiso d D 1 . .
H H1N 0.4167(19) 0.757(2) 0.5039(15) 0.031(6) Uiso d D 1 . .
H H2N 0.467(3) 0.6748(17) 0.3437(14) 0.046(7) 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 0.0000 '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 O1 H1O . . 110.1(18) ?
C12 O4 H4O . . 112.4(19) ?
O1 C1 C6 . . 117.41(15) ?
O1 C1 C2 . . 122.70(15) ?
C6 C1 C2 . . 119.88(15) ?
C3 C2 C1 . . 119.90(16) ?
C3 C2 H2 . . 120.1 ?
C1 C2 H2 . . 120.1 ?
C2 C3 C4 . . 120.52(16) ?
C2 C3 H3 . . 119.7 ?
C4 C3 H3 . . 119.7 ?
C5 C4 C3 . . 119.15(15) ?
C5 C4 C7 . . 122.84(15) ?
C3 C4 C7 . . 118.02(15) ?
C6 C5 C4 . . 120.74(16) ?
C6 C5 H5 . . 119.6 ?
C4 C5 H5 . . 119.6 ?
C5 C6 C1 . . 119.80(16) ?
C5 C6 H6 . . 120.1 ?
C1 C6 H6 . . 120.1 ?
O2 C7 N1 . . 120.37(14) ?
O2 C7 C4 . . 122.52(15) ?
N1 C7 C4 . . 117.11(14) ?
O3 C8 N2 . . 120.18(16) ?
O3 C8 C9 . . 123.09(17) ?
N2 C8 C9 . . 116.72(15) ?
C10 C9 C14 . . 118.62(15) ?
C10 C9 C8 . . 117.85(15) ?
C14 C9 C8 . . 123.53(16) ?
C11 C10 C9 . . 121.10(16) ?
C11 C10 H10 . . 119.5 ?
C9 C10 H10 . . 119.5 ?
C10 C11 C12 . . 119.54(17) ?
C10 C11 H11 . . 120.2 ?
C12 C11 H11 . . 120.2 ?
O4 C12 C13 . . 117.63(15) ?
O4 C12 C11 . . 122.39(16) ?
C13 C12 C11 . . 119.98(15) ?
C14 C13 C12 . . 119.96(16) ?
C14 C13 H13 . . 120.0 ?
C12 C13 H13 . . 120.0 ?
C13 C14 C9 . . 120.80(17) ?
C13 C14 H14 . . 119.6 ?
C9 C14 H14 . . 119.6 ?
C7 N1 N2 . . 119.10(14) ?
C7 N1 H1N . . 125.3(15) ?
N2 N1 H1N . . 114.8(16) ?
C8 N2 N1 . . 119.49(14) ?
C8 N2 H2N . . 121.9(16) ?
N1 N2 H2N . . 114.5(16) ?
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
O1 C1 . 1.3506(19) ?
O1 H1O . 0.839(10) ?
O2 C7 . 1.237(2) ?
O3 C8 . 1.223(2) ?
O4 C12 . 1.3497(19) ?
O4 H4O . 0.846(10) ?
C1 C6 . 1.392(2) ?
C1 C2 . 1.396(2) ?
C2 C3 . 1.385(2) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.395(2) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.393(2) ?
C4 C7 . 1.477(2) ?
C5 C6 . 1.386(2) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 N1 . 1.345(2) ?
C8 N2 . 1.354(2) ?
C8 C9 . 1.485(2) ?
C9 C10 . 1.392(2) ?
C9 C14 . 1.400(2) ?
C10 C11 . 1.388(2) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.398(2) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.390(2) ?
C13 C14 . 1.385(2) ?
C13 H13 . 0.9500 ?
C14 H14 . 0.9500 ?
N1 N2 . 1.3856(18) ?
N1 H1N . 0.877(10) ?
N2 H2N . 0.874(10) ?
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
O1 H1o O2 2_665 0.840(10) 1.850(10) 2.684(2) 172(3) yes
O4 H4o O3 2_674 0.850(10) 1.830(10) 2.675(2) 178(3) yes
N1 H1n O2 4_466 0.880(10) 2.080(10) 2.920(2) 162(2) yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 C2 C3 . . . . 178.36(16) ?
C6 C1 C2 C3 . . . . -1.0(3) ?
C1 C2 C3 C4 . . . . -0.4(3) ?
C2 C3 C4 C5 . . . . 1.0(3) ?
C2 C3 C4 C7 . . . . -179.43(16) ?
C3 C4 C5 C6 . . . . -0.2(3) ?
C7 C4 C5 C6 . . . . -179.74(16) ?
C4 C5 C6 C1 . . . . -1.2(3) ?
O1 C1 C6 C5 . . . . -177.59(17) ?
C2 C1 C6 C5 . . . . 1.8(3) ?
C5 C4 C7 O2 . . . . 152.83(17) ?
C3 C4 C7 O2 . . . . -26.7(2) ?
C5 C4 C7 N1 . . . . -27.4(2) ?
C3 C4 C7 N1 . . . . 153.10(16) ?
O3 C8 C9 C10 . . . . 10.2(3) ?
N2 C8 C9 C10 . . . . -170.57(16) ?
O3 C8 C9 C14 . . . . -170.11(19) ?
N2 C8 C9 C14 . . . . 9.1(3) ?
C14 C9 C10 C11 . . . . 0.4(3) ?
C8 C9 C10 C11 . . . . -179.92(17) ?
C9 C10 C11 C12 . . . . 0.6(3) ?
C10 C11 C12 O4 . . . . 178.43(16) ?
C10 C11 C12 C13 . . . . -1.1(3) ?
O4 C12 C13 C14 . . . . -178.89(17) ?
C11 C12 C13 C14 . . . . 0.6(3) ?
C12 C13 C14 C9 . . . . 0.3(3) ?
C10 C9 C14 C13 . . . . -0.9(3) ?
C8 C9 C14 C13 . . . . 179.49(17) ?
O2 C7 N1 N2 . . . . -4.4(2) ?
C4 C7 N1 N2 . . . . 175.75(14) ?
O3 C8 N2 N1 . . . . -7.3(3) ?
C9 C8 N2 N1 . . . . 173.48(15) ?
C7 N1 N2 C8 . . . . -72.5(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9555169
