#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/54/2205419.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_2205419
loop_
_publ_author_name
'Ali, Hapipah M.'
'Puvaneswary, Subramaniam'
'Basirun, Wan Jefri'
'Ng, Seik Weng'
_publ_section_title
;
 3-Hydroxysalicylaldehyde benzoylhydrazone
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1013
_journal_page_last               o1014
_journal_paper_doi               10.1107/S1600536805007555
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C14 H12 N2 O3'
_chemical_formula_moiety         'C14 H12 N2 O3'
_chemical_formula_sum            'C14 H12 N2 O3'
_chemical_formula_weight         256.26
_chemical_name_systematic
;
3-Hydroxysalicylaldehyde benzoylhydrazone
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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            8
_cell_length_a                   10.6030(6)
_cell_length_b                   9.7780(6)
_cell_length_c                   25.203(2)
_cell_measurement_reflns_used    3480
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      23.8
_cell_measurement_theta_min      2.5
_cell_volume                     2612.9(3)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device_type  'Bruker SMART area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'medium-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.033
_diffrn_reflns_av_sigmaI/netI    0.027
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            14751
_diffrn_reflns_theta_full        27.0
_diffrn_reflns_theta_max         27.0
_diffrn_reflns_theta_min         2.5
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.14
_refine_diff_density_min         -0.15
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2855
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0400
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0597P)²+0.3349P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1243
_reflns_number_gt                1651
_reflns_number_total             2855
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6624.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               2205419
_cod_database_fobs_code          2205419
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
loop_
_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_type_symbol
O1 0.5061(2) 0.5996(2) 0.41965(6) 0.0889(5) Uani d D 1 O
O2 0.58010(10) 0.63420(10) 0.52152(5) 0.0649(4) Uani d D 1 O
O3 0.71870(10) 0.58260(10) 0.65676(5) 0.0668(4) Uani d . 1 O
N1 0.69710(10) 0.78550(10) 0.58850(5) 0.0524(4) Uani d . 1 N
N2 0.7490(2) 0.80440(10) 0.63790(5) 0.0520(4) Uani d D 1 N
C1 0.5928(2) 0.7422(2) 0.48773(6) 0.0532(4) Uani d . 1 C
C2 0.5534(2) 0.7225(2) 0.43570(7) 0.0646(5) Uani d . 1 C
C3 0.5631(2) 0.8273(2) 0.39990(8) 0.0796(6) Uani d . 1 C
C4 0.6112(2) 0.9521(2) 0.41513(8) 0.0817(6) Uani d . 1 C
C5 0.6519(2) 0.9720(2) 0.46615(7) 0.0705(5) Uani d . 1 C
C6 0.6443(2) 0.8667(2) 0.50329(6) 0.0540(4) Uani d . 1 C
C7 0.6936(2) 0.8862(2) 0.55645(6) 0.0556(4) Uani d . 1 C
C8 0.7599(2) 0.6950(2) 0.66983(6) 0.0497(4) Uani d . 1 C
C9 0.8237(2) 0.7178(2) 0.72173(6) 0.0504(4) Uani d . 1 C
C10 0.9097(2) 0.8210(2) 0.73034(7) 0.0626(5) Uani d . 1 C
C11 0.9679(2) 0.8325(2) 0.77915(8) 0.0793(6) Uani d . 1 C
C12 0.9412(2) 0.7426(3) 0.81879(8) 0.0830(6) Uani d . 1 C
C13 0.8572(2) 0.6397(3) 0.81063(8) 0.0874(7) Uani d . 1 C
C14 0.7984(2) 0.6268(2) 0.76232(7) 0.0739(6) Uani d . 1 C
H1o 0.509(3) 0.542(2) 0.4454(9) 0.160(10) Uiso d D 1 H
H2o 0.614(2) 0.663(2) 0.5502(6) 0.100(10) Uiso d D 1 H
H2n 0.771(2) 0.8860(10) 0.6468(7) 0.070(10) Uiso d D 1 H
H3 0.5370 0.8141 0.3650 0.096 Uiso calc R 1 H
H4 0.6162 1.0231 0.3907 0.098 Uiso calc R 1 H
H5 0.6847 1.0564 0.4761 0.085 Uiso calc R 1 H
H7 0.7225 0.9718 0.5671 0.067 Uiso calc R 1 H
H10 0.9285 0.8827 0.7034 0.075 Uiso calc R 1 H
H11 1.0258 0.9023 0.7850 0.095 Uiso calc R 1 H
H12 0.9806 0.7515 0.8516 0.100 Uiso calc R 1 H
H13 0.8395 0.5781 0.8377 0.105 Uiso calc R 1 H
H14 0.7411 0.5561 0.7569 0.089 Uiso calc R 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.1180(10) 0.0880(10) 0.0610(10) -0.0270(10) -0.0260(10) -0.0030(10)
O2 0.0920(10) 0.0520(10) 0.0500(10) -0.0110(10) -0.0120(10) 0.0030(10)
O3 0.1080(10) 0.0360(10) 0.0570(10) -0.0060(10) -0.0060(10) -0.0050(10)
N1 0.0700(10) 0.0460(10) 0.0410(10) -0.0040(10) -0.0040(10) -0.0010(10)
N2 0.0790(10) 0.0360(10) 0.0410(10) -0.0060(10) -0.0060(10) -0.0030(10)
C1 0.0580(10) 0.0560(10) 0.0460(10) 0.0010(10) -0.0030(10) 0.0030(10)
C2 0.0680(10) 0.0730(10) 0.0530(10) -0.0090(10) -0.0110(10) 0.0020(10)
C3 0.088(2) 0.098(2) 0.0530(10) -0.0150(10) -0.0180(10) 0.0140(10)
C4 0.094(2) 0.089(2) 0.0620(10) -0.0130(10) -0.0140(10) 0.0320(10)
C5 0.0850(10) 0.0640(10) 0.0630(10) -0.0100(10) -0.0090(10) 0.0170(10)
C6 0.0600(10) 0.0540(10) 0.0480(10) 0.0030(10) -0.0020(10) 0.0060(10)
C7 0.0720(10) 0.0440(10) 0.0510(10) -0.0050(10) -0.0010(10) 0.0000(10)
C8 0.0680(10) 0.0360(10) 0.0450(10) 0.0020(10) 0.0030(10) -0.0050(10)
C9 0.0650(10) 0.0420(10) 0.0440(10) 0.0090(10) 0.0030(10) -0.0050(10)
C10 0.0730(10) 0.0550(10) 0.0600(10) 0.0010(10) -0.0080(10) -0.0010(10)
C11 0.082(2) 0.0800(10) 0.0760(10) -0.0030(10) -0.0220(10) -0.0080(10)
C12 0.087(2) 0.109(2) 0.0530(10) 0.0140(10) -0.0170(10) -0.0060(10)
C13 0.101(2) 0.111(2) 0.0500(10) -0.005(2) -0.0050(10) 0.0160(10)
C14 0.092(2) 0.0750(10) 0.0550(10) -0.0110(10) -0.0040(10) 0.0100(10)
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'
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
C7 N1 N2 118.80(10) no
C8 N2 N1 118.00(10) no
O2 C1 C2 116.9(2) no
O2 C1 C6 122.70(10) no
C2 C1 C6 120.4(2) no
O1 C2 C3 119.4(2) no
O1 C2 C1 120.9(2) no
C3 C2 C1 119.7(2) no
C2 C3 C4 120.5(2) no
C5 C4 C3 120.3(2) no
C4 C5 C6 120.5(2) no
C1 C6 C5 118.7(2) no
C1 C6 C7 121.10(10) no
C5 C6 C7 120.2(2) no
N1 C7 C6 119.6(2) no
O3 C8 N2 121.4(2) no
O3 C8 C9 122.10(10) no
N2 C8 C9 116.50(10) no
C10 C9 C14 118.9(2) no
C10 C9 C8 123.3(2) no
C14 C9 C8 117.7(2) no
C9 C10 C11 119.7(2) no
C12 C11 C10 120.6(2) no
C13 C12 C11 120.24(19) no
C12 C13 C14 120.0(2) no
C13 C14 C9 120.6(2) no
C2 O1 H1o 110(2) no
C1 O2 H2o 103(2) no
C8 N2 H2n 124.0(10) no
N1 N2 H2n 118.0(10) no
C2 C3 H3 119.8 no
C4 C3 H3 119.8 no
C5 C4 H4 119.9 no
C3 C4 H4 119.9 no
C4 C5 H5 119.8 no
C6 C5 H5 119.8 no
N1 C7 H7 120.2 no
C6 C7 H7 120.2 no
C9 C10 H10 120.1 no
C11 C10 H10 120.1 no
C12 C11 H11 119.7 no
C10 C11 H11 119.7 no
C13 C12 H12 119.9 no
C11 C12 H12 119.9 no
C12 C13 H13 120.0 no
C14 C13 H13 120.0 no
C13 C14 H14 119.7 no
C9 C14 H14 119.7 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 1.363(2) no
O2 C1 1.363(2) no
O3 C8 1.227(2) no
N1 C7 1.275(2) no
N1 N2 1.374(2) no
N2 C8 1.344(2) no
C1 C2 1.390(2) no
C1 C6 1.391(2) no
C2 C3 1.369(3) no
C3 C4 1.377(3) no
C4 C5 1.370(3) no
C5 C6 1.394(2) no
C6 C7 1.451(2) no
C8 C9 1.489(2) no
C9 C10 1.377(2) no
C9 C14 1.382(2) no
C10 C11 1.381(3) no
C11 C12 1.361(3) no
C12 C13 1.359(3) no
C13 C14 1.374(3) no
O1 H1o 0.860(10) no
O2 H2o 0.860(10) no
N2 H2n 0.860(10) no
C3 H3 0.93 no
C4 H4 0.93 no
C5 H5 0.93 no
C7 H7 0.93 no
C10 H10 0.93 no
C11 H11 0.93 no
C12 H12 0.93 no
C13 H13 0.93 no
C14 H14 0.93 no
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 . 0.860(10) 2.25(3) 2.706(2) 113(2) yes
O1 H1o O2 5_666 0.860(10) 2.14(2) 2.874(2) 144(3) yes
O2 H2o N1 . 0.860(10) 1.770(10) 2.564(2) 153(2) yes
N2 H2n O3 7_765 0.860(10) 1.940(10) 2.783(2) 165(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
_geom_torsion_publ_flag
C7 N1 N2 C8 -175.5(2) no
O2 C1 C2 O1 -0.9(3) no
C6 C1 C2 O1 178.1(2) no
O2 C1 C2 C3 179.7(2) no
C6 C1 C2 C3 -1.3(3) no
O1 C2 C3 C4 -179.7(2) no
C1 C2 C3 C4 -0.2(3) no
C2 C3 C4 C5 1.0(3) no
C3 C4 C5 C6 -0.4(3) no
O2 C1 C6 C5 -179.1(2) no
C2 C1 C6 C5 2.0(3) no
O2 C1 C6 C7 3.0(3) no
C2 C1 C6 C7 -175.9(2) no
C4 C5 C6 C1 -1.1(3) no
C4 C5 C6 C7 176.7(2) no
N2 N1 C7 C6 177.3(2) no
C1 C6 C7 N1 4.4(3) no
C5 C6 C7 N1 -173.4(2) no
N1 N2 C8 O3 -3.9(3) no
N1 N2 C8 C9 176.40(10) no
O3 C8 C9 C10 155.1(2) no
N2 C8 C9 C10 -25.2(2) no
O3 C8 C9 C14 -22.2(2) no
N2 C8 C9 C14 157.5(2) no
C14 C9 C10 C11 -0.6(3) no
C8 C9 C10 C11 -177.8(2) no
C9 C10 C11 C12 0.1(3) no
C10 C11 C12 C13 0.3(3) no
C11 C12 C13 C14 -0.3(4) no
C12 C13 C14 C9 -0.1(3) no
C10 C9 C14 C13 0.6(3) no
C8 C9 C14 C13 178.0(2) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 20180211
