##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2011-12-28
_journal_date_accepted     2011-12-29
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2012
_journal_volume     68
_journal_issue      2
_journal_page_first     o324
_journal_page_last     o325
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536811056182
_journal_coeditor_code     SU2361
_publ_contact_author_name     'Prof. Tahir, Muhammad Nawaz'
_publ_contact_author_address
;
Department of Physics
University of Sargodha
Punjab, Pakistan
;
_publ_contact_author_email     dmntahir_uos@yahoo.com
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
(E)-1-(2-Hydroxy-5-methoxybenzylidene)thiosemicarbazide
;
loop_
    _publ_author_name
    _publ_author_address
    'Adabi Ardakani, Amir'
;
Ardakan Branch,
Islamic Azad University,
Ardakan,
Iran
;
    'Kargar, Hadi'
;
      Department of Chemistry,
      Payame Noor University,
      PO BOX 19395-3697 Tehran,
      I. R. of IRAN
;
    'Kia, Reza'
;
      X-ray Crystallography Lab.,
      Plasma Physics Research Center,
      Science and Research Branch,
      Islamic Azad University,
      Tehran,
      Iran
      and
      Department of Chemistry,
      Science and Research Branch,
      Islamic Azad University,
      Tehran,
      Iran
;
    'Tahir, Muhammad Nawaz'
;
Department of Physics
University of Sargodha
Punjab, Pakistan
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(E)-1-(2-Hydroxy-5-methoxybenzylidene)thiosemicarbazide
;
_chemical_name_common
;
;
_chemical_formula_moiety     'C9 H11 N3 O2 S'
_chemical_formula_sum     'C9 H11 N3 O2 S'
_chemical_formula_iupac     'C9 H11 N3 O2 S'
_chemical_formula_weight     225.27
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
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'
_cell_length_a     7.4878(2)
_cell_length_b     9.9880(2)
_cell_length_c     14.3754(3)
_cell_angle_alpha     90.00
_cell_angle_beta     91.8460(10)
_cell_angle_gamma     90.00
_cell_volume     1074.55(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2750
_cell_measurement_theta_min     2.37
_cell_measurement_theta_max     27.49
_cell_measurement_temperature     291(2)
_exptl_crystal_description     'Plate'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.24
_exptl_crystal_size_mid     0.14
_exptl_crystal_size_min     0.08
_exptl_crystal_density_diffrn     1.392
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     472
_exptl_absorpt_coefficient_mu     0.285
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min     0.7999
_exptl_absorpt_correction_T_max     0.9262
_exptl_special_details     ?
_diffrn_ambient_temperature     291(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector
;
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     10176
_diffrn_reflns_av_R_equivalents     0.0164
_diffrn_reflns_av_sigmaI/netI     0.0135
_diffrn_reflns_theta_min     2.48
_diffrn_reflns_theta_max     28.36
_diffrn_reflns_theta_full     28.36
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     19
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     2673
_reflns_number_gt     2365
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0398
_refine_ls_R_factor_gt     0.0354
_refine_ls_wR_factor_gt     0.1058
_refine_ls_wR_factor_ref     0.1100
_refine_ls_goodness_of_fit_ref     1.074
_refine_ls_restrained_S_all     1.074
_refine_ls_number_reflns     2673
_refine_ls_number_parameters     138
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0594P)²+0.2733P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.313
_refine_diff_density_min     -0.238
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'APEX2 (Bruker, 2005)'
_computing_cell_refinement     'SAINT (Bruker, 2005)'
_computing_data_reduction     'SAINT (Bruker, 2005)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
                             'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
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
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.26170(16) 0.48062(13) 0.97372(9) 0.0346(3) Uani d . 1 1 . .
    C C2 0.24057(17) 0.58273(14) 1.03826(10) 0.0386(3) Uani d . 1 1 . .
    C C3 0.2907(2) 0.71257(15) 1.01635(13) 0.0510(4) Uani d . 1 1 . .
    H H3 0.2758 0.7812 1.0591 0.061 Uiso calc R 1 1 . .
    C C4 0.3626(2) 0.73967(16) 0.93147(14) 0.0573(4) Uani d . 1 1 . .
    H H4 0.3962 0.8268 0.9175 0.069 Uiso calc R 1 1 . .
    C C5 0.3857(2) 0.63922(17) 0.86653(12) 0.0512(4) Uani d . 1 1 . .
    C C6 0.33436(19) 0.51057(16) 0.88716(10) 0.0438(3) Uani d . 1 1 . .
    H H6 0.3478 0.4429 0.8435 0.053 Uiso calc R 1 1 . .
    C C7 0.4842(3) 0.5753(3) 0.71703(14) 0.0797(7) Uani d . 1 1 . .
    H H7A 0.5574 0.5054 0.7437 0.120 Uiso calc R 1 1 . .
    H H7B 0.5415 0.6124 0.6641 0.120 Uiso calc R 1 1 . .
    H H7C 0.3701 0.5392 0.6978 0.120 Uiso calc R 1 1 . .
    C C8 0.21137(17) 0.34293(13) 0.99115(9) 0.0365(3) Uani d . 1 1 . .
    H H8 0.2270 0.2798 0.9445 0.044 Uiso calc R 1 1 . .
    C C9 0.02639(18) 0.11834(12) 1.14708(9) 0.0353(3) Uani d . 1 1 . .
    N N1 0.14624(14) 0.30443(10) 1.06812(8) 0.0349(2) Uani d . 1 1 . .
    N N2 0.10299(16) 0.17032(11) 1.07211(8) 0.0388(3) Uani d . 1 1 . .
    H H2 0.1255 0.1192 1.0258 0.047 Uiso calc R 1 1 . .
    N N3 0.0098(2) 0.19397(12) 1.22149(8) 0.0507(3) Uani d . 1 1 . .
    H H3A 0.0478 0.2752 1.2214 0.061 Uiso calc R 1 1 . .
    H H3B -0.0390 0.1620 1.2701 0.061 Uiso calc R 1 1 . .
    O O1 0.17090(17) 0.56061(11) 1.12351(8) 0.0514(3) Uani d . 1 1 . .
    H H1 0.1484 0.4807 1.1292 0.077 Uiso calc R 1 1 . .
    O O2 0.4601(2) 0.67718(16) 0.78420(11) 0.0777(4) Uani d . 1 1 . .
    S S1 -0.04238(6) -0.04281(3) 1.14369(3) 0.04739(14) Uani d . 1 1 . .
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
    C1 0.0324(6) 0.0336(6) 0.0378(6) -0.0011(5) 0.0011(5) 0.0040(5)
    C2 0.0356(6) 0.0346(6) 0.0455(7) 0.0003(5) 0.0019(5) 0.0011(5)
    C3 0.0486(8) 0.0323(7) 0.0722(10) -0.0006(6) 0.0028(7) -0.0008(7)
    C4 0.0489(8) 0.0387(7) 0.0844(12) -0.0041(6) 0.0022(8) 0.0213(8)
    C5 0.0422(7) 0.0543(9) 0.0573(9) -0.0021(6) 0.0051(6) 0.0232(7)
    C6 0.0430(7) 0.0474(8) 0.0411(7) -0.0017(6) 0.0048(5) 0.0072(6)
    C7 0.0654(11) 0.123(2) 0.0515(10) 0.0004(12) 0.0163(9) 0.0260(12)
    C8 0.0411(6) 0.0329(6) 0.0356(6) -0.0024(5) 0.0041(5) -0.0009(5)
    C9 0.0440(6) 0.0293(6) 0.0326(6) 0.0004(5) 0.0021(5) 0.0016(5)
    N1 0.0401(5) 0.0285(5) 0.0362(5) -0.0025(4) 0.0027(4) 0.0010(4)
    N2 0.0540(6) 0.0282(5) 0.0346(5) -0.0040(4) 0.0091(5) -0.0012(4)
    N3 0.0834(9) 0.0347(6) 0.0347(6) -0.0109(6) 0.0138(6) -0.0034(5)
    O1 0.0678(7) 0.0401(5) 0.0473(6) -0.0046(5) 0.0163(5) -0.0072(4)
    O2 0.0770(9) 0.0822(10) 0.0750(9) -0.0103(7) 0.0193(7) 0.0389(8)
    S1 0.0754(3) 0.02908(19) 0.0382(2) -0.00904(14) 0.01049(17) 0.00096(12)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    C1 C2 . 1.3912(19) ?
    C1 C6 . 1.4063(18) ?
    C1 C8 . 1.4499(17) ?
    C2 O1 . 1.3653(17) ?
    C2 C3 . 1.389(2) ?
    C3 C4 . 1.376(2) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.385(3) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.376(2) ?
    C5 O2 . 1.3774(19) ?
    C6 H6 . 0.9300 ?
    C7 O2 . 1.418(3) ?
    C7 H7A . 0.9600 ?
    C7 H7B . 0.9600 ?
    C7 H7C . 0.9600 ?
    C8 N1 . 1.2824(16) ?
    C8 H8 . 0.9300 ?
    C9 N3 . 1.3187(17) ?
    C9 N2 . 1.3415(16) ?
    C9 S1 . 1.6901(13) ?
    N1 N2 . 1.3797(14) ?
    N2 H2 . 0.8600 ?
    N3 H3A . 0.8600 ?
    N3 H3B . 0.8600 ?
    O1 H1 . 0.8200 ?
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
    C2 C1 C6 . . 119.32(13) ?
    C2 C1 C8 . . 122.98(12) ?
    C6 C1 C8 . . 117.70(12) ?
    O1 C2 C3 . . 117.94(13) ?
    O1 C2 C1 . . 122.33(12) ?
    C3 C2 C1 . . 119.72(13) ?
    C4 C3 C2 . . 120.06(15) ?
    C4 C3 H3 . . 120.0 ?
    C2 C3 H3 . . 120.0 ?
    C3 C4 C5 . . 121.07(14) ?
    C3 C4 H4 . . 119.5 ?
    C5 C4 H4 . . 119.5 ?
    C6 C5 O2 . . 124.45(17) ?
    C6 C5 C4 . . 119.29(14) ?
    O2 C5 C4 . . 116.26(15) ?
    C5 C6 C1 . . 120.53(15) ?
    C5 C6 H6 . . 119.7 ?
    C1 C6 H6 . . 119.7 ?
    O2 C7 H7A . . 109.5 ?
    O2 C7 H7B . . 109.5 ?
    H7A C7 H7B . . 109.5 ?
    O2 C7 H7C . . 109.5 ?
    H7A C7 H7C . . 109.5 ?
    H7B C7 H7C . . 109.5 ?
    N1 C8 C1 . . 122.80(12) ?
    N1 C8 H8 . . 118.6 ?
    C1 C8 H8 . . 118.6 ?
    N3 C9 N2 . . 118.93(12) ?
    N3 C9 S1 . . 122.17(10) ?
    N2 C9 S1 . . 118.89(10) ?
    C8 N1 N2 . . 115.04(11) ?
    C9 N2 N1 . . 121.08(11) ?
    C9 N2 H2 . . 119.5 ?
    N1 N2 H2 . . 119.5 ?
    C9 N3 H3A . . 120.0 ?
    C9 N3 H3B . . 120.0 ?
    H3A N3 H3B . . 120.0 ?
    C2 O1 H1 . . 109.5 ?
    C5 O2 C7 . . 116.83(15) ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C6 C1 C2 O1 . . . . 179.97(12) ?
    C8 C1 C2 O1 . . . . 0.2(2) ?
    C6 C1 C2 C3 . . . . 0.2(2) ?
    C8 C1 C2 C3 . . . . -179.54(13) ?
    O1 C2 C3 C4 . . . . 179.62(14) ?
    C1 C2 C3 C4 . . . . -0.6(2) ?
    C2 C3 C4 C5 . . . . 0.2(2) ?
    C3 C4 C5 C6 . . . . 0.6(2) ?
    C3 C4 C5 O2 . . . . -179.49(14) ?
    O2 C5 C6 C1 . . . . 179.10(14) ?
    C4 C5 C6 C1 . . . . -1.0(2) ?
    C2 C1 C6 C5 . . . . 0.6(2) ?
    C8 C1 C6 C5 . . . . -179.64(13) ?
    C2 C1 C8 N1 . . . . -1.2(2) ?
    C6 C1 C8 N1 . . . . 179.03(12) ?
    C1 C8 N1 N2 . . . . 178.93(11) ?
    N3 C9 N2 N1 . . . . -7.2(2) ?
    S1 C9 N2 N1 . . . . 173.92(10) ?
    C8 N1 N2 C9 . . . . -177.01(12) ?
    C6 C5 O2 C7 . . . . 0.0(2) ?
    C4 C5 O2 C7 . . . . -179.90(16) ?
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 H1 N1 . 0.82 1.97 2.6844(15) 146 y
    N2 H2 S1 3_557 0.86 2.61 3.3706(12) 148 y
    N3 H3A S1 2_557 0.86 2.66 3.2706(12) 129 y
    N3 H3B O1 2_547 0.86 2.11 2.9604(17) 172 y
