#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/64/2226477.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_2226477
loop_
_publ_author_name
'Li, Yu-Feng'
'Jiang, Jin-He'
'Jian, Fang-Fang'
_publ_section_title
;
 N'-(4-Hydroxybenzylidene)thiophene-2-carbohydrazide
;
_journal_coeditor_code           HB5483
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1719
_journal_paper_doi               10.1107/S1600536810021483
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C12 H10 N2 O2 S'
_chemical_formula_moiety         'C12 H10 N2 O2 S'
_chemical_formula_sum            'C12 H10 N2 O2 S'
_chemical_formula_weight         246.28
_chemical_name_systematic
;
N'-(4-Hydroxybenzylidene)thiophene-2-carbohydrazide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 104.40(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.5622(19)
_cell_length_b                   12.404(3)
_cell_length_c                   9.991(2)
_cell_measurement_reflns_used    1501
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      3.11
_cell_volume                     1147.8(5)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART CCD'
_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  0.0570
_diffrn_reflns_av_sigmaI/netI    0.0486
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10889
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.11
_exptl_absorpt_coefficient_mu    0.272
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.375
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2629
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0963
_refine_ls_R_factor_gt           0.0481
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1300
_refine_ls_wR_factor_ref         0.1814
_reflns_number_gt                1501
_reflns_number_total             2629
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5483.cif
_cod_data_source_block           I
_cod_original_cell_volume        1147.8(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2226477
_cod_database_fobs_code          2226477
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
S S1 0.89443(10) 0.07271(7) 0.19012(8) 0.0713(3) Uani d . 1 . .
N N2 1.2232(2) 0.37439(19) 0.1118(2) 0.0452(6) Uani d . 1 . .
O O1 1.1172(2) 0.24125(17) 0.27388(17) 0.0548(6) Uani d . 1 . .
N N1 1.1217(2) 0.29541(19) 0.0602(2) 0.0482(6) Uani d . 1 . .
H H1A 1.0911 0.2863 -0.0275 0.058 Uiso calc R 1 . .
C C12 1.4377(3) 0.5507(2) 0.1730(3) 0.0464(6) Uani d . 1 . .
H H12A 1.4518 0.4976 0.2407 0.056 Uiso calc R 1 . .
C C4 0.9590(3) 0.1566(2) 0.0840(2) 0.0435(6) Uani d . 1 . .
C C5 1.0717(3) 0.2334(2) 0.1475(2) 0.0406(6) Uani d . 1 . .
C C7 1.3299(3) 0.5378(2) 0.0519(2) 0.0430(6) Uani d . 1 . .
C C6 1.2339(3) 0.4464(2) 0.0230(3) 0.0483(7) Uani d . 1 . .
H H6A 1.1759 0.4392 -0.0663 0.058 Uiso calc R 1 . .
C C11 1.5235(3) 0.6408(2) 0.1941(3) 0.0506(7) Uani d . 1 . .
H H11A 1.5936 0.6491 0.2767 0.061 Uiso calc R 1 . .
O O2 1.5867(3) 0.81085(19) 0.1088(2) 0.0816(8) Uani d . 1 . .
H H2C 1.6718 0.7957 0.1418 0.122 Uiso calc R 1 . .
C C10 1.5063(3) 0.7198(2) 0.0930(3) 0.0518(7) Uani d . 1 . .
C C8 1.3140(3) 0.6189(2) -0.0471(3) 0.0510(7) Uani d . 1 . .
H H8A 1.2427 0.6120 -0.1291 0.061 Uiso calc R 1 . .
C C9 1.3999(3) 0.7083(2) -0.0273(3) 0.0569(8) Uani d . 1 . .
H H9A 1.3866 0.7613 -0.0951 0.068 Uiso calc R 1 . .
C C3 0.8883(4) 0.1398(3) -0.0502(3) 0.0647(9) Uani d . 1 . .
H H3A 0.9077 0.1779 -0.1237 0.078 Uiso calc R 1 . .
C C2 0.7834(4) 0.0591(3) -0.0662(3) 0.0756(11) Uani d . 1 . .
H H2B 0.7253 0.0377 -0.1512 0.091 Uiso calc R 1 . .
C C1 0.7759(4) 0.0163(3) 0.0548(3) 0.0765(11) Uani d . 1 . .
H H1B 0.7124 -0.0386 0.0632 0.092 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 0.0016 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 S1 C4 . . 91.70(14) ?
C6 N2 N1 . . 113.9(2) ?
C5 N1 N2 . . 119.68(19) ?
C5 N1 H1A . . 120.2 ?
N2 N1 H1A . . 120.2 ?
C11 C12 C7 . . 120.9(2) ?
C11 C12 H12A . . 119.6 ?
C7 C12 H12A . . 119.6 ?
C3 C4 C5 . . 131.4(2) ?
C3 C4 S1 . . 110.6(2) ?
C5 C4 S1 . . 118.01(18) ?
O1 C5 N1 . . 122.0(2) ?
O1 C5 C4 . . 122.1(2) ?
N1 C5 C4 . . 115.9(2) ?
C12 C7 C8 . . 117.5(3) ?
C12 C7 C6 . . 124.2(2) ?
C8 C7 C6 . . 118.3(2) ?
N2 C6 C7 . . 124.5(2) ?
N2 C6 H6A . . 117.8 ?
C7 C6 H6A . . 117.8 ?
C12 C11 C10 . . 120.3(3) ?
C12 C11 H11A . . 119.8 ?
C10 C11 H11A . . 119.8 ?
C10 O2 H2C . . 109.5 ?
O2 C10 C9 . . 117.6(3) ?
O2 C10 C11 . . 122.9(3) ?
C9 C10 C11 . . 119.5(3) ?
C9 C8 C7 . . 121.9(3) ?
C9 C8 H8A . . 119.1 ?
C7 C8 H8A . . 119.1 ?
C8 C9 C10 . . 119.9(3) ?
C8 C9 H9A . . 120.0 ?
C10 C9 H9A . . 120.0 ?
C4 C3 C2 . . 112.9(3) ?
C4 C3 H3A . . 123.5 ?
C2 C3 H3A . . 123.5 ?
C1 C2 C3 . . 112.3(3) ?
C1 C2 H2B . . 123.9 ?
C3 C2 H2B . . 123.9 ?
C2 C1 S1 . . 112.6(3) ?
C2 C1 H1B . . 123.7 ?
S1 C1 H1B . . 123.7 ?
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
S1 C1 . 1.685(4) ?
S1 C4 . 1.707(2) ?
N2 C6 . 1.281(3) ?
N2 N1 . 1.385(3) ?
O1 C5 . 1.233(3) ?
N1 C5 . 1.337(3) ?
N1 H1A . 0.8600 ?
C12 C11 . 1.371(4) ?
C12 C7 . 1.390(4) ?
C12 H12A . 0.9300 ?
C4 C3 . 1.360(4) ?
C4 C5 . 1.461(4) ?
C7 C8 . 1.392(4) ?
C7 C6 . 1.443(4) ?
C6 H6A . 0.9300 ?
C11 C10 . 1.387(4) ?
C11 H11A . 0.9300 ?
O2 C10 . 1.354(3) ?
O2 H2C . 0.8200 ?
C10 C9 . 1.375(4) ?
C8 C9 . 1.364(4) ?
C8 H8A . 0.9300 ?
C9 H9A . 0.9300 ?
C3 C2 . 1.398(4) ?
C3 H3A . 0.9300 ?
C2 C1 . 1.339(4) ?
C2 H2B . 0.9300 ?
C1 H1B . 0.9300 ?
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 H1A O1 4_565 0.86 2.09 2.887(3) 154
O2 H2C O1 2_855 0.82 2.10 2.913(3) 174
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10858625
