#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/78/2217843.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_2217843
loop_
_publ_author_name
'Sarıkavaklı, Nursabah'
'Babahan, knur'
'Şahin, Ertan'
'Hökelek, Tuncer'
_publ_section_title
;
 2-Hydroxyimino-1-phenylethanone thiosemicarbazone monohydrate
;
_journal_coeditor_code           XU2403
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o623
_journal_page_last               o624
_journal_paper_doi               10.1107/S1600536808004947
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C9 H10 N4 O S, H2 O'
_chemical_formula_moiety         'C9 H10 N4 O S, H2 O'
_chemical_formula_sum            'C9 H12 N4 O2 S'
_chemical_formula_weight         240.29
_chemical_melting_point          443
_chemical_name_systematic
;
2-Hydroxyimino-1-phenylethanone thiosemicarbazone monohydrate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 127.24(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   28.5615(3)
_cell_length_b                   4.6805(3)
_cell_length_c                   22.0977(4)
_cell_measurement_reflns_used    2893
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      30.5214
_cell_measurement_theta_min      2.3153
_cell_volume                     2351.8(6)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2005)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID-S'
_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  0.0898
_diffrn_reflns_av_sigmaI/netI    0.0553
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            31269
_diffrn_reflns_theta_full        30.54
_diffrn_reflns_theta_max         30.54
_diffrn_reflns_theta_min         2.32
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.268
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.309
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3607
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.1063
_refine_ls_R_factor_gt           0.0618
_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)+(0.0474P)²+0.9027P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1340
_refine_ls_wR_factor_ref         0.1543
_reflns_number_gt                2146
_reflns_number_total             3607
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2403.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2217843
_cod_database_fobs_code          2217843
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
S S1 0.08587(3) 0.69943(16) 0.58554(3) 0.0693(2) Uani d . 1
O O1 0.24428(8) 0.9359(4) 0.88734(10) 0.0740(5) Uani d D 1
H H1A 0.2527(12) 1.022(6) 0.8584(15) 0.100(10) Uiso d D 1
O O2 0.22848(8) 0.6577(4) 0.70204(11) 0.0720(5) Uani d D 1
H H21 0.1878(8) 0.692(7) 0.6673(16) 0.133(14) Uiso d D 1
H H22 0.2445(13) 0.817(5) 0.7313(16) 0.113(12) Uiso d D 1
N N1 0.19953(8) 0.7460(4) 0.83853(10) 0.0576(5) Uani d . 1
N N2 0.09978(8) 0.3607(4) 0.75639(10) 0.0577(5) Uani d . 1
N N3 0.10929(9) 0.5206(5) 0.71329(10) 0.0619(5) Uani d D 1
H H3A 0.1412(9) 0.641(5) 0.7347(14) 0.077(8) Uiso d D 1
N N4 0.02448(9) 0.3422(5) 0.60650(11) 0.0654(6) Uani d D 1
H H41 -0.0011(10) 0.316(5) 0.5550(10) 0.076(8) Uiso d D 1
H H42 0.0210(12) 0.238(5) 0.6394(14) 0.084(9) Uiso d D 1
C C1 0.07415(11) 0.0295(6) 0.83508(14) 0.0644(6) Uani d . 1
H H1 0.0517(11) 0.012(5) 0.7826(15) 0.074(8) Uiso d . 1
C C2 0.06113(12) -0.1405(6) 0.87378(17) 0.0721(7) Uani d . 1
H H2 0.0280(11) -0.257(5) 0.8455(15) 0.071(8) Uiso d . 1
C C3 0.09577(13) -0.1362(6) 0.95201(17) 0.0724(7) Uani d . 1
H H3 0.0859(12) -0.245(6) 0.9780(16) 0.083(9) Uiso d . 1
C C4 0.14393(14) 0.0388(6) 0.99041(16) 0.0742(7) Uani d . 1
H H4 0.1666(12) 0.036(6) 1.0426(16) 0.092(9) Uiso d . 1
C C5 0.15737(13) 0.2112(6) 0.95211(14) 0.0639(6) Uani d . 1
H H5 0.1913(13) 0.330(6) 0.9810(17) 0.089(9) Uiso d . 1
C C6 0.12248(9) 0.2111(5) 0.87338(12) 0.0521(5) Uani d . 1
C C7 0.13487(9) 0.3927(5) 0.82959(11) 0.0516(5) Uani d . 1
C C8 0.18351(10) 0.5985(5) 0.87101(13) 0.0580(6) Uani d . 1
H H8 0.2005(11) 0.621(5) 0.9241(15) 0.080(8) Uiso d . 1
C C9 0.07134(10) 0.5057(5) 0.63645(11) 0.0556(5) Uani 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 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1250 0.1230 '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
N1 O1 H1A 104.6(19)
H21 O2 H22 106(3)
C8 N1 O1 112.88(19)
C7 N2 N3 118.58(19)
C9 N3 N2 120.1(2)
C9 N3 H3A 117.9(16)
N2 N3 H3A 122.0(17)
C9 N4 H41 120.3(17)
C9 N4 H42 117.9(17)
H41 N4 H42 121(2)
C2 C1 C6 121.2(2)
C2 C1 H1 118.9(16)
C6 C1 H1 119.7(16)
C1 C2 C3 120.9(3)
C1 C2 H2 118.0(16)
C3 C2 H2 121.1(16)
C4 C3 C2 118.4(3)
C4 C3 H3 120.7(18)
C2 C3 H3 120.8(18)
C3 C4 C5 121.2(3)
C3 C4 H4 116.6(19)
C5 C4 H4 122.2(19)
C4 C5 C6 120.9(3)
C4 C5 H5 118.5(18)
C6 C5 H5 120.6(18)
C1 C6 C7 119.6(2)
C5 C6 C1 117.3(2)
C5 C6 C7 123.0(2)
N2 C7 C8 125.4(2)
N2 C7 C6 116.00(19)
C8 C7 C6 118.60(18)
N1 C8 C7 122.4(2)
N1 C8 H8 122.8(16)
C7 C8 H8 114.7(16)
N4 C9 N3 117.2(2)
N4 C9 S1 124.28(17)
N3 C9 S1 118.46(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C9 1.681(2)
O1 H1A 0.903(18)
O2 H21 0.940(17)
O2 H22 0.907(18)
N1 O1 1.385(2)
N1 C8 1.264(3)
N2 N3 1.362(3)
N2 C7 1.297(3)
N3 H3A 0.923(17)
N4 C9 1.320(3)
N4 H41 0.915(17)
N4 H42 0.930(17)
C1 C2 1.374(3)
C1 H1 0.93(2)
C2 H2 0.93(3)
C3 C2 1.378(4)
C3 C4 1.368(4)
C3 H3 0.93(3)
C4 H4 0.92(3)
C5 C4 1.381(4)
C5 H5 0.95(3)
C6 C1 1.389(3)
C6 C5 1.386(3)
C6 C7 1.483(3)
C7 C8 1.469(3)
C8 H8 0.97(3)
C9 N3 1.355(3)
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 H1A O2 4_556 0.90(3) 1.83(3) 2.728(3) 174(3)
O2 H21 S1 . 0.94(3) 2.32(3) 3.250(3) 171(3)
O2 H22 O2 4_556 0.91(3) 1.98(3) 2.886(3) 172(4)
N3 H3A N1 . 0.92(3) 1.91(2) 2.604(3) 130(2)
N4 H41 S1 5_566 0.92(2) 2.53(2) 3.434(2) 169(3)
N4 H42 N2 . 0.93(3) 2.24(3) 2.643(3) 105(2)
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
O1 N1 C8 C7 177.1(2)
C7 N2 N3 C9 -175.9(2)
N3 N2 C7 C8 2.8(3)
N3 N2 C7 C6 -179.56(19)
C6 C1 C2 C3 -0.1(4)
C4 C3 C2 C1 -0.8(4)
C2 C3 C4 C5 1.0(4)
C6 C5 C4 C3 -0.3(4)
C5 C6 C1 C2 0.8(4)
C7 C6 C1 C2 -179.6(2)
C1 C6 C5 C4 -0.6(4)
C7 C6 C5 C4 179.8(2)
C5 C6 C7 N2 177.2(2)
C1 C6 C7 N2 -2.4(3)
C5 C6 C7 C8 -5.0(3)
C1 C6 C7 C8 175.4(2)
N2 C7 C8 N1 -7.6(4)
C6 C7 C8 N1 174.8(2)
S1 C9 N3 N2 -178.23(16)
N4 C9 N3 N2 3.0(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655456
