#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/54/2205426.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_2205426
loop_
_publ_author_name
'Ali, Hapipah M.'
'Puvaneswary, Subramaniam'
'Basirun, Wan Jefri'
'Ng, Seik Weng'
_publ_section_title
;
 3-Hydroxysalicylaldehyde 2-thienoylhydrazone
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1083
_journal_page_last               o1084
_journal_paper_doi               10.1107/S160053680500841X
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C12 H10 N2 O3 S'
_chemical_formula_moiety         'C12 H10 N2 O3 S'
_chemical_formula_sum            'C12 H10 N2 O3 S'
_chemical_formula_weight         262.28
_chemical_name_systematic
;
3-Hydroxysalicylaldehyde 2-thienoylhydrazone
;
_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
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.9940(10)
_cell_length_b                   11.990(2)
_cell_length_c                   24.787(4)
_cell_measurement_reflns_used    814
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      22.4
_cell_measurement_theta_min      3.1
_cell_volume                     2375.8(6)
_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 0.99
_diffrn_measured_fraction_theta_max 0.99
_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  0.024
_diffrn_reflns_av_sigmaI/netI    0.045
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            10174
_diffrn_reflns_theta_full        27.2
_diffrn_reflns_theta_max         27.2
_diffrn_reflns_theta_min         1.9
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.274
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'Faint yellow--orange'
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.28
_refine_diff_density_min         -0.40
_refine_ls_abs_structure_details 'Flack (1983), 2201 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.05(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.03
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         5149
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.03
_refine_ls_R_factor_all          0.082
_refine_ls_R_factor_gt           0.045
_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)+(0.0638P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.104
_refine_ls_wR_factor_ref         0.121
_reflns_number_gt                3383
_reflns_number_total             5149
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6632.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_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:

'_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               2205426
_cod_database_fobs_code          2205426
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'
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
S1 0.35970(10) 0.60172(8) 0.77784(4) 0.0690(3) Uani d . 1 S
O1 0.8484(3) 0.1702(2) 1.05580(10) 0.0555(6) Uani d . 1 O
O2 0.7107(3) 0.3025(2) 0.98500(10) 0.0631(7) Uani d . 1 O
O3 0.4717(3) 0.4562(2) 0.86500(10) 0.0619(6) Uani d . 1 O
N1 0.6344(3) 0.5093(2) 0.95550(10) 0.0443(6) Uani d . 1 N
N2 0.5815(3) 0.5882(2) 0.91940(10) 0.0457(6) Uani d . 1 N
C1 0.7805(4) 0.3519(2) 1.02890(10) 0.0420(10) Uani d . 1 C
C2 0.8544(4) 0.2821(2) 1.06630(10) 0.0420(10) Uani d . 1 C
C3 0.9260(4) 0.3269(2) 1.11220(10) 0.0490(10) Uani d . 1 C
C4 0.9252(4) 0.4396(2) 1.12060(10) 0.0520(10) Uani d . 1 C
C5 0.8542(4) 0.5090(2) 1.08350(10) 0.0470(10) Uani d . 1 C
C6 0.7811(3) 0.4676(2) 1.03670(10) 0.0380(10) Uani d . 1 C
C7 0.7140(4) 0.5435(2) 0.99690(10) 0.0440(10) Uani d . 1 C
C8 0.5075(4) 0.5536(2) 0.87330(10) 0.0450(10) Uani d . 1 C
C9 0.4724(4) 0.6412(2) 0.83310(10) 0.0450(10) Uani d . 1 C
C10 0.5161(4) 0.7521(2) 0.83140(10) 0.0500(10) Uani d . 1 C
C11 0.4522(5) 0.8028(3) 0.78440(10) 0.0710(10) Uani d . 1 C
C12 0.3670(5) 0.7319(3) 0.75270(10) 0.0730(10) Uani d . 1 C
S1' 0.0760(2) 0.72486(8) 0.92850(10) 0.0790(3) Uani d . 1 S
O1' 0.6317(4) 0.5334(2) 1.25480(10) 0.0871(9) Uani d . 1 O
O2' 0.4460(3) 0.5700(2) 1.16660(10) 0.0676(6) Uani d . 1 O
O3' 0.1817(3) 0.6811(2) 1.04290(10) 0.0597(6) Uani d . 1 O
N1' 0.3243(3) 0.4899(2) 1.07760(10) 0.0464(6) Uani d . 1 N
N2' 0.2515(3) 0.5009(2) 1.02780(10) 0.0488(6) Uani d . 1 N
C1' 0.4981(4) 0.4643(3) 1.17610(10) 0.0480(10) Uani d . 1 C
C2' 0.5925(4) 0.4460(3) 1.22200(10) 0.0580(10) Uani d . 1 C
C3' 0.6503(5) 0.3408(3) 1.23410(10) 0.0680(10) Uani d . 1 C
C4' 0.6127(5) 0.2535(3) 1.20070(10) 0.0700(10) Uani d . 1 C
C5' 0.5212(4) 0.2691(3) 1.15500(10) 0.0610(10) Uani d . 1 C
C6' 0.4625(4) 0.3754(2) 1.14110(10) 0.0470(10) Uani d . 1 C
C7' 0.3763(4) 0.3938(3) 1.09070(10) 0.0500(10) Uani d . 1 C
C8' 0.1843(3) 0.5991(3) 1.01300(10) 0.0460(10) Uani d . 1 C
C9' 0.1127(3) 0.6002(3) 0.95870(10) 0.0440(10) Uani d . 1 C
C10' 0.0664(4) 0.5137(3) 0.92550(10) 0.0540(10) Uani d . 1 C
C11' -0.0026(4) 0.5523(3) 0.87690(10) 0.0660(10) Uani d . 1 C
C12' -0.0015(5) 0.6624(3) 0.8728(2) 0.0740(10) Uani d . 1 C
H1o 0.8930 0.1346 1.0818 0.067 Uiso calc R 1 H
H2o 0.6785 0.3523 0.9629 0.076 Uiso calc R 1 H
H2n 0.5949 0.6573 0.9259 0.055 Uiso calc R 1 H
H3 0.9750 0.2800 1.1375 0.059 Uiso calc R 1 H
H4 0.9733 0.4689 1.1517 0.063 Uiso calc R 1 H
H5 0.8546 0.5856 1.0897 0.057 Uiso calc R 1 H
H7 0.7294 0.6198 1.0016 0.052 Uiso calc R 1 H
H10 0.5790 0.7884 0.8576 0.060 Uiso calc R 1 H
H11 0.4675 0.8779 0.7763 0.085 Uiso calc R 1 H
H12 0.3174 0.7526 0.7202 0.087 Uiso calc R 1 H
H1o' 0.6106 0.5944 1.2387 0.105 Uiso calc R 1 H
H2o' 0.4059 0.5743 1.1349 0.081 Uiso calc R 1 H
H2n' 0.2488 0.4457 1.0063 0.059 Uiso calc R 1 H
H3' 0.7145 0.3292 1.2649 0.082 Uiso calc R 1 H
H4' 0.6503 0.1823 1.2093 0.084 Uiso calc R 1 H
H5' 0.4974 0.2086 1.1328 0.073 Uiso calc R 1 H
H7' 0.3585 0.3341 1.0675 0.060 Uiso calc R 1 H
H10' 0.0792 0.4387 0.9342 0.064 Uiso calc R 1 H
H11' -0.0447 0.5054 0.8502 0.079 Uiso calc R 1 H
H12' -0.0392 0.7011 0.8426 0.088 Uiso calc R 1 H
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'
S S 0.1246 0.1234 '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
C12 S1 C9 91.3(2) no
C7 N1 N2 117.2(2) no
C8 N2 N1 118.4(2) no
O2 C1 C2 116.6(2) no
O2 C1 C6 122.9(2) no
C2 C1 C6 120.4(3) no
O1 C2 C1 116.9(2) no
O1 C2 C3 123.5(2) no
C1 C2 C3 119.6(3) no
C4 C3 C2 120.6(3) no
C5 C4 C3 120.1(3) no
C4 C5 C6 121.3(3) no
C5 C6 C1 118.1(3) no
C5 C6 C7 120.0(2) no
C1 C6 C7 121.9(3) no
N1 C7 C6 122.1(2) no
O3 C8 N2 122.6(3) no
O3 C8 C9 121.5(3) no
N2 C8 C9 115.9(2) no
C10 C9 C8 131.3(3) no
C10 C9 S1 112.2(2) no
C8 C9 S1 116.5(2) no
C9 C10 C11 110.5(3) no
C12 C11 C10 113.2(3) no
C11 C12 S1 112.8(3) no
C12' S1' C9' 91.9(2) no
C7' N1' N2' 117.3(2) no
C8' N2' N1' 120.0(2) no
O2' C1' C2' 117.3(3) no
O2' C1' C6' 122.7(3) no
C2' C1' C6' 119.9(3) no
O1' C2' C3' 119.8(3) no
O1' C2' C1' 119.6(3) no
C3' C2' C1' 120.6(3) no
C4' C3' C2' 119.6(3) no
C5' C4' C3' 121.1(3) no
C4' C5' C6' 120.7(3) no
C5' C6' C1' 118.0(3) no
C5' C6' C7' 120.8(3) no
C1' C6' C7' 121.0(3) no
N1' C7' C6' 121.2(3) no
C10' C9' C8' 130.4(3) no
C10' C9' S1' 110.8(2) no
C8' C9' S1' 118.8(2) no
O3' C8' N2' 122.8(3) no
O3' C8' C9' 122.7(3) no
N2' C8' C9' 114.6(3) no
C9' C10' C11' 111.7(3) no
C12' C11' C10' 113.0(3) no
C11' C12' S1' 112.5(3) no
C2 O1 H1o 109.5 no
C1 O2 H2o 109.5 no
C8 N2 H2n 120.8 no
N1 N2 H2n 120.8 no
C4 C3 H3 119.7 no
C2 C3 H3 119.7 no
C5 C4 H4 119.9 no
C3 C4 H4 119.9 no
C4 C5 H5 119.4 no
C6 C5 H5 119.4 no
N1 C7 H7 119.0 no
C6 C7 H7 119.0 no
C9 C10 H10 124.8 no
C11 C10 H10 124.8 no
C12 C11 H11 123.4 no
C10 C11 H11 123.4 no
C11 C12 H12 123.6 no
S1 C12 H12 123.6 no
C2' O1' H1o' 109.5 no
C1' O2' H2o' 109.5 no
C8' N2' H2n' 120.0 no
N1' N2' H2n' 120.0 no
C4' C3' H3' 120.2 no
C2' C3' H3' 120.2 no
C5' C4' H4' 119.5 no
C3' C4' H4' 119.5 no
C4' C5' H5' 119.6 no
C6' C5' H5' 119.6 no
N1' C7' H7' 119.4 no
C6' C7' H7' 119.4 no
C9' C10' H10' 124.1 no
C11' C10' H10' 124.1 no
C12' C11' H11' 123.5 no
C10' C11' H11' 123.5 no
C11' C12' H12' 123.7 no
S1' C12' H12' 123.7 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C12 1.682(4) no
S1 C9 1.706(3) no
O1 C2 1.368(3) no
O2 C1 1.360(3) no
O3 C8 1.220(3) no
N1 C7 1.276(4) no
N1 N2 1.369(3) no
N2 C8 1.352(4) no
C1 C2 1.381(4) no
C1 C6 1.400(4) no
C2 C3 1.382(4) no
C3 C4 1.367(4) no
C4 C5 1.365(4) no
C5 C6 1.391(4) no
C6 C7 1.445(4) no
C8 C9 1.476(4) no
C9 C10 1.375(4) no
C10 C11 1.410(4) no
C11 C12 1.345(5) no
S1' C12' 1.687(4) no
S1' C9' 1.697(3) no
O1' C2' 1.364(4) no
O2' C1' 1.353(4) no
O3' C8' 1.231(3) no
N1' C7' 1.267(4) no
N1' N2' 1.371(3) no
N2' C8' 1.345(4) no
C1' C2' 1.383(4) no
C1' C6' 1.404(4) no
C2' C3' 1.377(5) no
C3' C4' 1.369(5) no
C4' C5' 1.361(4) no
C5' C6' 1.402(4) no
C6' C7' 1.442(4) no
C9' C10' 1.374(4) no
C9' C8' 1.463(4) no
C10' C11' 1.405(4) no
C11' C12' 1.324(5) no
O1 H1o 0.85 no
O2 H2o 0.85 no
N2 H2n 0.85 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
O1' H1o' 0.85 no
O2' H2o' 0.85 no
N2' H2n' 0.85 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
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 O3 3_557 0.85 1.82 2.668(3) 173 yes
O2 H2o N1 . 0.85 1.92 2.656(3) 144 yes
N2 H2n O3' 3_567 0.85 2.20 3.028(3) 165 yes
O1' H1o' O2' . 0.85 2.24 2.679(3) 112 yes
O2' H2o' N1' . 0.85 1.86 2.595(3) 144 yes
N2' H2n' O1 3_457 0.85 2.22 3.017(3) 156 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 175.3(3) no
O2 C1 C2 O1 -0.8(4) no
C6 C1 C2 O1 179.9(3) no
O2 C1 C2 C3 -179.3(3) no
C6 C1 C2 C3 1.4(4) no
O1 C2 C3 C4 -178.9(3) no
C1 C2 C3 C4 -0.5(5) no
C2 C3 C4 C5 -0.3(5) no
C3 C4 C5 C6 0.1(5) no
C4 C5 C6 C1 0.8(5) no
C4 C5 C6 C7 -177.0(3) no
O2 C1 C6 C5 179.2(3) no
C2 C1 C6 C5 -1.5(5) no
O2 C1 C6 C7 -3.1(5) no
C2 C1 C6 C7 176.2(2) no
N2 N1 C7 C6 -177.8(2) no
C5 C6 C7 N1 -174.4(3) no
C1 C6 C7 N1 7.9(4) no
N1 N2 C8 O3 7.3(4) no
N1 N2 C8 C9 -172.6(2) no
O3 C8 C9 C10 -172.6(3) no
N2 C8 C9 C10 7.3(4) no
O3 C8 C9 S1 6.7(4) no
N2 C8 C9 S1 -173.4(2) no
C12 S1 C9 C10 -0.8(2) no
C12 S1 C9 C8 179.7(2) no
C8 C9 C10 C11 -179.6(3) no
S1 C9 C10 C11 1.0(3) no
C9 C10 C11 C12 -0.7(4) no
C10 C11 C12 S1 0.1(4) no
C9 S1 C12 C11 0.4(3) no
C7' N1' N2' C8' 175.7(3) no
O2' C1' C2' O1' -1.2(5) no
C6' C1' C2' O1' 177.7(3) no
O2' C1' C2' C3' -179.8(3) no
C6' C1' C2' C3' -0.9(5) no
O1' C2' C3' C4' -179.1(3) no
C1' C2' C3' C4' -0.5(5) no
C2' C3' C4' C5' 1.1(6) no
C3' C4' C5' C6' -0.2(5) no
C4' C5' C6' C1' -1.2(5) no
C4' C5' C6' C7' 175.3(3) no
O2' C1' C6' C5' -179.4(3) no
C2' C1' C6' C5' 1.7(4) no
O2' C1' C6' C7' 4.0(4) no
C2' C1' C6' C7' -174.8(3) no
N2' N1' C7' C6' 176.7(2) no
C5' C6' C7' N1' -179.3(3) no
C1' C6' C7' N1' -2.8(4) no
C12' S1' C9' C10' 0.5(3) no
C12' S1' C9' C8' -179.3(2) no
N1' N2' C8' O3' -1.5(5) no
N1' N2' C8' C9' 179.2(2) no
C10' C9' C8' O3' -161.6(3) no
S1' C9' C8' O3' 18.2(4) no
C10' C9' C8' N2' 17.7(5) no
S1' C9' C8' N2' -162.5(2) no
C8' C9' C10' C11' 178.0(3) no
S1' C9' C10' C11' -1.8(3) no
C9' C10' C11' C12' 2.6(5) no
C10' C11' C12' S1' -2.2(5) no
C9' S1' C12' C11' 1.0(3) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 23264379
