#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/11/2231186.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_2231186
loop_
_publ_author_name
'Schmitt, Bonell'
'Gerber, Thomas'
'Hosten, Eric'
'Betz, Richard'
_publ_section_title
;
 A monoclinic polymorph of
 (1E,5E)-1,5-bis(2-hydroxybenzylidene)thiocarbonohydrazide
;
_journal_coeditor_code           KJ2182
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2206
_journal_page_last               o2207
_journal_paper_doi               10.1107/S1600536811030340
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C15 H14 N4 O2 S'
_chemical_formula_moiety         'C15 H14 N4 O2 S'
_chemical_formula_sum            'C15 H14 N4 O2 S'
_chemical_formula_weight         314.36
_chemical_name_systematic
;
(1E,5E)-1,5-bis(2-hydroxybenzylidene)thiocarbonohydrazide
;
_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                 91.2250(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.60200(10)
_cell_length_b                   7.4260(2)
_cell_length_c                   34.5220(8)
_cell_measurement_reflns_used    3781
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.16
_cell_measurement_theta_min      3.27
_cell_volume                     1435.80(6)
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            13304
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         2.36
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8785
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2008)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.203
_exptl_crystal_size_mid          0.168
_exptl_crystal_size_min          0.104
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.302
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3578
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0484
_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)+(0.0459P)²+0.6828P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1087
_refine_ls_wR_factor_ref         0.1155
_reflns_number_gt                2830
_reflns_number_total             3578
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            kj2182.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2231186
_cod_database_fobs_code          2231186
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_symmetry_multiplicity
S S1 0.12373(8) 0.21558(7) 0.258163(14) 0.02903(14) Uani d . 1 1
O O1 0.1741(2) 0.2387(2) 0.36537(4) 0.0324(3) Uani d . 1 1
H H81 0.2203 0.2637 0.3430 0.049 Uiso calc R 1 1
O O2 -0.1378(2) 0.2458(2) 0.15547(4) 0.0383(4) Uani d . 1 1
H H82 -0.0382 0.2723 0.1731 0.057 Uiso calc R 1 1
N N1 0.5251(3) 0.3922(2) 0.27723(4) 0.0281(4) Uani d . 1 1
H H71 0.646(4) 0.457(3) 0.2711(6) 0.037(6) Uiso d . 1 1
N N2 0.4749(3) 0.3542(2) 0.31484(4) 0.0265(3) Uani d . 1 1
N N3 0.4199(3) 0.4051(2) 0.21391(5) 0.0294(4) Uani d . 1 1
H H73 0.546(5) 0.466(4) 0.2103(7) 0.053(8) Uiso d . 1 1
N N4 0.2684(3) 0.3694(2) 0.18331(4) 0.0274(3) Uani d . 1 1
C C1 0.3648(3) 0.3442(2) 0.24941(5) 0.0248(4) Uani d . 1 1
C C2 0.6209(3) 0.4048(2) 0.34167(5) 0.0256(4) Uani d . 1 1
H H2 0.7674 0.4613 0.3355 0.031 Uiso calc R 1 1
C C3 0.3279(3) 0.4210(2) 0.14954(5) 0.0255(4) Uani d . 1 1
H H3 0.4739 0.4834 0.1460 0.031 Uiso calc R 1 1
C C11 0.5583(3) 0.3740(2) 0.38171(5) 0.0237(4) Uani d . 1 1
C C12 0.3391(3) 0.2956(3) 0.39193(5) 0.0258(4) Uani d . 1 1
C C13 0.2860(3) 0.2726(3) 0.43090(6) 0.0303(4) Uani d . 1 1
H H13 0.1391 0.2186 0.4378 0.036 Uiso calc R 1 1
C C14 0.4458(4) 0.3279(3) 0.45949(6) 0.0319(4) Uani d . 1 1
H H14 0.4073 0.3126 0.4860 0.038 Uiso calc R 1 1
C C15 0.6625(4) 0.4057(3) 0.44992(6) 0.0312(4) Uani d . 1 1
H H15 0.7718 0.4439 0.4697 0.037 Uiso calc R 1 1
C C16 0.7166(3) 0.4266(3) 0.41139(6) 0.0270(4) Uani d . 1 1
H H16 0.8656 0.4783 0.4049 0.032 Uiso calc R 1 1
C C21 0.1696(3) 0.3832(2) 0.11659(5) 0.0239(4) Uani d . 1 1
C C22 -0.0524(3) 0.2973(3) 0.12065(6) 0.0287(4) Uani d . 1 1
C C23 -0.1919(4) 0.2586(3) 0.08796(6) 0.0345(5) Uani d . 1 1
H H23 -0.3413 0.2000 0.0907 0.041 Uiso calc R 1 1
C C24 -0.1148(4) 0.3048(3) 0.05168(6) 0.0368(5) Uani d . 1 1
H H24 -0.2114 0.2772 0.0295 0.044 Uiso calc R 1 1
C C25 0.1036(4) 0.3915(3) 0.04711(6) 0.0336(5) Uani d . 1 1
H H25 0.1562 0.4234 0.0221 0.040 Uiso calc R 1 1
C C26 0.2414(3) 0.4301(3) 0.07948(5) 0.0277(4) Uani d . 1 1
H H26 0.3896 0.4903 0.0765 0.033 Uiso calc R 1 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
C12 O1 H81 109.5
C22 O2 H82 109.5
C1 N1 N2 118.38(15)
C1 N1 H71 119.2(15)
N2 N1 H71 121.9(15)
C2 N2 N1 119.14(16)
C1 N3 N4 119.14(16)
C1 N3 H73 121.2(17)
N4 N3 H73 119.7(17)
C3 N4 N3 118.46(16)
N3 C1 N1 113.38(16)
N3 C1 S1 123.54(14)
N1 C1 S1 123.06(14)
N2 C2 C11 118.67(16)
N2 C2 H2 120.7
C11 C2 H2 120.7
N4 C3 C21 119.25(17)
N4 C3 H3 120.4
C21 C3 H3 120.4
C16 C11 C12 118.32(17)
C16 C11 C2 119.49(16)
C12 C11 C2 122.18(17)
O1 C12 C13 117.24(16)
O1 C12 C11 122.97(16)
C13 C12 C11 119.79(17)
C14 C13 C12 120.30(18)
C14 C13 H13 119.9
C12 C13 H13 119.9
C13 C14 C15 120.65(17)
C13 C14 H14 119.7
C15 C14 H14 119.7
C16 C15 C14 119.13(18)
C16 C15 H15 120.4
C14 C15 H15 120.4
C15 C16 C11 121.80(18)
C15 C16 H16 119.1
C11 C16 H16 119.1
C26 C21 C22 118.51(17)
C26 C21 C3 119.15(16)
C22 C21 C3 122.33(17)
O2 C22 C23 117.24(17)
O2 C22 C21 123.01(17)
C23 C22 C21 119.73(18)
C24 C23 C22 120.37(19)
C24 C23 H23 119.8
C22 C23 H23 119.8
C23 C24 C25 120.72(19)
C23 C24 H24 119.6
C25 C24 H24 119.6
C26 C25 C24 118.90(19)
C26 C25 H25 120.6
C24 C25 H25 120.6
C25 C26 C21 121.76(18)
C25 C26 H26 119.1
C21 C26 H26 119.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.6867(19)
O1 C12 1.356(2)
O1 H81 0.8400
O2 C22 1.359(2)
O2 H82 0.8400
N1 C1 1.349(2)
N1 N2 1.364(2)
N1 H71 0.86(2)
N2 C2 1.279(2)
N3 C1 1.348(2)
N3 N4 1.367(2)
N3 H73 0.85(3)
N4 C3 1.278(2)
C2 C11 1.451(2)
C2 H2 0.9500
C3 C21 1.455(2)
C3 H3 0.9500
C11 C16 1.396(3)
C11 C12 1.411(2)
C12 C13 1.394(3)
C13 C14 1.381(3)
C13 H13 0.9500
C14 C15 1.390(3)
C14 H14 0.9500
C15 C16 1.379(3)
C15 H15 0.9500
C16 H16 0.9500
C21 C26 1.395(3)
C21 C22 1.407(3)
C22 C23 1.389(3)
C23 C24 1.377(3)
C23 H23 0.9500
C24 C25 1.394(3)
C24 H24 0.9500
C25 C26 1.375(3)
C25 H25 0.9500
C26 H26 0.9500
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
O1 H81 N2 . 0.84 1.87 2.597(2) 144.2
O1 H81 S1 . 0.84 2.99 3.7096(14) 145.2
O2 H82 N4 . 0.84 1.89 2.617(2) 144.3
O2 H82 S1 . 0.84 3.08 3.8135(16) 146.6
N1 H71 S1 2_655 0.86(2) 2.53(2) 3.3514(17) 159(2)
N3 H73 S1 2_655 0.85(3) 2.82(3) 3.5605(18) 147(2)
C16 H16 <i>C</i>~g~2 2_655 0.95 2.81 3.423(2) 123
C26 H26 <i>C</i>~g~1 2_655 0.95 2.74 3.438(2) 130
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
C1 N1 N2 C2 -177.46(17)
C1 N3 N4 C3 -176.94(18)
N4 N3 C1 N1 -178.39(16)
N4 N3 C1 S1 3.2(3)
N2 N1 C1 N3 173.21(16)
N2 N1 C1 S1 -8.4(2)
N1 N2 C2 C11 176.08(16)
N3 N4 C3 C21 179.64(16)
N2 C2 C11 C16 179.37(17)
N2 C2 C11 C12 -2.0(3)
C16 C11 C12 O1 -179.45(17)
C2 C11 C12 O1 1.9(3)
C16 C11 C12 C13 0.0(3)
C2 C11 C12 C13 -178.65(17)
O1 C12 C13 C14 -179.87(17)
C11 C12 C13 C14 0.7(3)
C12 C13 C14 C15 -0.6(3)
C13 C14 C15 C16 -0.2(3)
C14 C15 C16 C11 0.8(3)
C12 C11 C16 C15 -0.7(3)
C2 C11 C16 C15 177.92(17)
N4 C3 C21 C26 -176.19(17)
N4 C3 C21 C22 2.4(3)
C26 C21 C22 O2 179.74(17)
C3 C21 C22 O2 1.1(3)
C26 C21 C22 C23 1.1(3)
C3 C21 C22 C23 -177.55(17)
O2 C22 C23 C24 -179.10(18)
C21 C22 C23 C24 -0.4(3)
C22 C23 C24 C25 -0.2(3)
C23 C24 C25 C26 0.1(3)
C24 C25 C26 C21 0.6(3)
C22 C21 C26 C25 -1.2(3)
C3 C21 C26 C25 177.45(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656857
