##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# 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 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. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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#                                                                            #
# 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.                                        #
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##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
1-(2-Hydroxybenzoyl)thiosemicarbazide hemihydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H20 N6 O5 S2'
_chemical_formula_sum     'C16 H20 N6 O5 S2'
_chemical_formula_iupac     'C16 H20 N6 O5 S2'
_chemical_formula_weight     440.50
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     9.0718(11)
_cell_length_b     21.608(2)
_cell_length_c     10.1035(13)
_cell_angle_alpha     90.00
_cell_angle_beta     90.1730(10)
_cell_angle_gamma     90.00
_cell_volume     1980.5(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2367
_cell_measurement_theta_min     2.225
_cell_measurement_theta_max     25.686
_cell_measurement_temperature     298(2)
_exptl_crystal_description     block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.45
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.17
_exptl_crystal_density_diffrn     1.474
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     916
_exptl_absorpt_coefficient_mu     0.311
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.8727
_exptl_absorpt_correction_T_max     0.9490
_exptl_special_details
;
;
_diffrn_ambient_temperature     298(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 APEX CCD area-detector'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     9862
_diffrn_reflns_av_R_equivalents     0.0406
_diffrn_reflns_av_sigmaI/netI     0.0544
_diffrn_reflns_theta_min     1.88
_diffrn_reflns_theta_max     25.02
_diffrn_reflns_theta_full     25.02
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -21
_diffrn_reflns_limit_k_max     25
_diffrn_reflns_limit_l_min     -11
_diffrn_reflns_limit_l_max     12
_diffrn_standards_number     ?
_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 >
σ(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     3487
_reflns_number_gt     2202
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0864
_refine_ls_R_factor_gt     0.0465
_refine_ls_wR_factor_gt     0.1010
_refine_ls_wR_factor_ref     0.1221
_refine_ls_goodness_of_fit_ref     1.013
_refine_ls_restrained_S_all     1.013
_refine_ls_number_reflns     3487
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0468P)²+1.2463P] 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     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.372
_refine_diff_density_min     -0.325
_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     'SMART (Bruker, 2007)'
_computing_cell_refinement     'SAINT (Bruker, 2007)'
_computing_data_reduction     'SAINT (Bruker, 2007)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
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
    N N1 0.4021(3) 0.07227(12) 0.5682(3) 0.0401(7) Uani d . 1 . .
    H H1 0.3330 0.0634 0.6231 0.048 Uiso calc R 1 . .
    N N2 0.5273(3) 0.10117(11) 0.6152(3) 0.0392(7) Uani d . 1 . .
    H H2 0.6033 0.0794 0.6354 0.047 Uiso calc R 1 . .
    N N3 0.4849(3) 0.07466(12) 0.3544(3) 0.0443(7) Uani d . 1 . .
    H H3A 0.5612 0.0950 0.3806 0.053 Uiso calc R 1 . .
    H H3B 0.4746 0.0655 0.2721 0.053 Uiso calc R 1 . .
    N N4 0.8800(3) 0.06010(11) 0.3372(3) 0.0399(7) Uani d . 1 . .
    H H4' 0.8275 0.0385 0.3908 0.048 Uiso calc R 1 . .
    N N5 0.9398(3) 0.11556(11) 0.3803(3) 0.0362(7) Uani d . 1 . .
    H H5 1.0322 0.1177 0.3992 0.043 Uiso calc R 1 . .
    N N6 0.9674(3) 0.07614(13) 0.1292(3) 0.0527(8) Uani d . 1 . .
    H H6A 0.9949 0.1125 0.1534 0.063 Uiso calc R 1 . .
    H H6B 0.9827 0.0639 0.0495 0.063 Uiso calc R 1 . .
    O O1 0.4251(2) 0.19444(10) 0.5943(2) 0.0386(6) Uani d . 1 . .
    O O2 0.5712(3) 0.29296(10) 0.6415(2) 0.0441(6) Uani d . 1 . .
    H H2A 0.5042 0.2722 0.6100 0.066 Uiso calc R 1 . .
    O O3 0.7237(2) 0.16510(10) 0.3629(2) 0.0439(6) Uani d . 1 . .
    O O4 1.1396(2) 0.17295(9) 0.5240(2) 0.0408(6) Uani d . 1 . .
    H H4 1.2180 0.1806 0.5612 0.061 Uiso calc R 1 . .
    O O5 0.3935(7) 0.0087(2) 0.0932(4) 0.172(2) Uani d . 1 . .
    H H5D 0.3575 -0.0063 0.1638 0.206 Uiso d PR 0.50 . .
    H H5B 0.4780 0.0030 0.0591 0.206 Uiso d PR 0.50 . .
    S S1 0.23175(9) 0.01686(4) 0.39559(9) 0.0415(3) Uani d . 1 . .
    S S2 0.84286(14) -0.03260(5) 0.17448(11) 0.0703(4) Uani d . 1 . .
    C C1 0.3839(4) 0.05757(13) 0.4406(3) 0.0336(8) Uani d . 1 . .
    C C2 0.5320(3) 0.16295(14) 0.6297(3) 0.0307(7) Uani d . 1 . .
    C C3 0.6647(3) 0.19040(13) 0.6870(3) 0.0287(7) Uani d . 1 . .
    C C4 0.6763(3) 0.25507(14) 0.6910(3) 0.0315(7) Uani d . 1 . .
    C C5 0.7998(4) 0.28273(16) 0.7474(3) 0.0404(8) Uani d . 1 . .
    H H5A 0.8066 0.3256 0.7513 0.049 Uiso calc R 1 . .
    C C6 0.9113(4) 0.24687(18) 0.7971(3) 0.0448(9) Uani d . 1 . .
    H H6 0.9938 0.2657 0.8342 0.054 Uiso calc R 1 . .
    C C7 0.9031(4) 0.18322(17) 0.7929(3) 0.0445(9) Uani d . 1 . .
    H H7 0.9797 0.1593 0.8267 0.053 Uiso calc R 1 . .
    C C8 0.7813(3) 0.15549(15) 0.7387(3) 0.0377(8) Uani d . 1 . .
    H H8 0.7761 0.1125 0.7361 0.045 Uiso calc R 1 . .
    C C9 0.9021(4) 0.03945(15) 0.2138(4) 0.0412(8) Uani d . 1 . .
    C C10 0.8546(3) 0.16613(14) 0.3929(3) 0.0307(7) Uani d . 1 . .
    C C11 0.9288(3) 0.22405(13) 0.4381(3) 0.0288(7) Uani d . 1 . .
    C C12 1.0660(3) 0.22665(13) 0.5004(3) 0.0303(7) Uani d . 1 . .
    C C13 1.1241(4) 0.28340(14) 0.5386(3) 0.0370(8) Uani d . 1 . .
    H H13 1.2142 0.2849 0.5826 0.044 Uiso calc R 1 . .
    C C14 1.0501(4) 0.33711(15) 0.5122(3) 0.0425(9) Uani d . 1 . .
    H H14 1.0910 0.3749 0.5365 0.051 Uiso calc R 1 . .
    C C15 0.9147(4) 0.33536(15) 0.4495(3) 0.0431(9) Uani d . 1 . .
    H H15 0.8642 0.3719 0.4314 0.052 Uiso calc R 1 . .
    C C16 0.8552(4) 0.27936(14) 0.4143(3) 0.0373(8) Uani d . 1 . .
    H H16 0.7633 0.2784 0.3733 0.045 Uiso calc R 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
    N1 C1 . 1.338(4) ?
    N1 N2 . 1.379(3) ?
    N1 H1 . 0.8600 ?
    N2 C2 . 1.344(4) ?
    N2 H2 . 0.8600 ?
    N3 C1 . 1.319(4) ?
    N3 H3A . 0.8600 ?
    N3 H3B . 0.8600 ?
    N4 C9 . 1.340(4) ?
    N4 N5 . 1.385(3) ?
    N4 H4' . 0.8600 ?
    N5 C10 . 1.345(4) ?
    N5 H5 . 0.8600 ?
    N6 C9 . 1.308(4) ?
    N6 H6A . 0.8600 ?
    N6 H6B . 0.8600 ?
    O1 C2 . 1.237(3) ?
    O2 C4 . 1.351(4) ?
    O2 H2A . 0.8200 ?
    O3 C10 . 1.225(3) ?
    O4 C12 . 1.359(3) ?
    O4 H4 . 0.8200 ?
    O5 H5D . 0.8496 ?
    O5 H5B . 0.8500 ?
    S1 C1 . 1.697(3) ?
    S2 C9 . 1.694(3) ?
    C2 C3 . 1.460(4) ?
    C3 C8 . 1.399(4) ?
    C3 C4 . 1.402(4) ?
    C4 C5 . 1.391(4) ?
    C5 C6 . 1.369(5) ?
    C5 H5A . 0.9300 ?
    C6 C7 . 1.378(5) ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.370(4) ?
    C7 H7 . 0.9300 ?
    C8 H8 . 0.9300 ?
    C10 C11 . 1.492(4) ?
    C11 C16 . 1.390(4) ?
    C11 C12 . 1.394(4) ?
    C12 C13 . 1.389(4) ?
    C13 C14 . 1.367(4) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.381(5) ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.371(4) ?
    C15 H15 . 0.9300 ?
    C16 H16 . 0.9300 ?
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 N1 N2 . . 122.6(3) ?
    C1 N1 H1 . . 118.7 ?
    N2 N1 H1 . . 118.7 ?
    C2 N2 N1 . . 120.9(3) ?
    C2 N2 H2 . . 119.5 ?
    N1 N2 H2 . . 119.5 ?
    C1 N3 H3A . . 120.0 ?
    C1 N3 H3B . . 120.0 ?
    H3A N3 H3B . . 120.0 ?
    C9 N4 N5 . . 121.4(3) ?
    C9 N4 H4' . . 119.3 ?
    N5 N4 H4' . . 119.3 ?
    C10 N5 N4 . . 120.5(3) ?
    C10 N5 H5 . . 119.7 ?
    N4 N5 H5 . . 119.7 ?
    C9 N6 H6A . . 120.0 ?
    C9 N6 H6B . . 120.0 ?
    H6A N6 H6B . . 120.0 ?
    C4 O2 H2A . . 109.5 ?
    C12 O4 H4 . . 109.5 ?
    H5D O5 H5B . . 129.4 ?
    N3 C1 N1 . . 119.1(3) ?
    N3 C1 S1 . . 122.3(3) ?
    N1 C1 S1 . . 118.6(3) ?
    O1 C2 N2 . . 119.4(3) ?
    O1 C2 C3 . . 122.4(3) ?
    N2 C2 C3 . . 118.2(3) ?
    C8 C3 C4 . . 118.1(3) ?
    C8 C3 C2 . . 123.4(3) ?
    C4 C3 C2 . . 118.5(3) ?
    O2 C4 C5 . . 117.2(3) ?
    O2 C4 C3 . . 122.7(3) ?
    C5 C4 C3 . . 120.0(3) ?
    C6 C5 C4 . . 120.1(3) ?
    C6 C5 H5A . . 120.0 ?
    C4 C5 H5A . . 120.0 ?
    C5 C6 C7 . . 120.9(3) ?
    C5 C6 H6 . . 119.5 ?
    C7 C6 H6 . . 119.5 ?
    C8 C7 C6 . . 119.5(3) ?
    C8 C7 H7 . . 120.3 ?
    C6 C7 H7 . . 120.3 ?
    C7 C8 C3 . . 121.4(3) ?
    C7 C8 H8 . . 119.3 ?
    C3 C8 H8 . . 119.3 ?
    N6 C9 N4 . . 118.4(3) ?
    N6 C9 S2 . . 123.2(3) ?
    N4 C9 S2 . . 118.4(3) ?
    O3 C10 N5 . . 121.3(3) ?
    O3 C10 C11 . . 121.8(3) ?
    N5 C10 C11 . . 116.8(3) ?
    C16 C11 C12 . . 118.1(3) ?
    C16 C11 C10 . . 116.9(3) ?
    C12 C11 C10 . . 125.0(3) ?
    O4 C12 C13 . . 121.3(3) ?
    O4 C12 C11 . . 118.8(3) ?
    C13 C12 C11 . . 119.9(3) ?
    C14 C13 C12 . . 120.6(3) ?
    C14 C13 H13 . . 119.7 ?
    C12 C13 H13 . . 119.7 ?
    C13 C14 C15 . . 120.2(3) ?
    C13 C14 H14 . . 119.9 ?
    C15 C14 H14 . . 119.9 ?
    C16 C15 C14 . . 119.5(3) ?
    C16 C15 H15 . . 120.3 ?
    C14 C15 H15 . . 120.3 ?
    C15 C16 C11 . . 121.7(3) ?
    C15 C16 H16 . . 119.2 ?
    C11 C16 H16 . . 119.2 ?
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
    N2 H2 S1 3_656 0.86 2.58 3.361(3) 151.4
    N5 H5 S1 1_655 0.86 2.83 3.404(3) 125.4
    N6 H6A O2 4_665 0.86 2.16 2.984(3) 160.3
    N6 H6B S2 3_755 0.86 2.85 3.647(3) 155.5
    O4 H4 O1 1_655 0.82 1.93 2.724(3) 162.3
    O5 H5B O5 3_655 0.85 1.95 2.728(10) 151.7
    N3 H3A O3 . 0.86 2.12 2.918(3) 153.7
    N3 H3B O5 . 0.86 2.30 3.110(5) 156.3
    N5 H5 O4 . 0.86 1.99 2.629(3) 130.3
    O2 H2A O1 . 0.82 1.83 2.552(3) 145.6
    O5 H5D S1 . 0.85 2.66 3.398(4) 146.7
data_global
_journal_date_recd_electronic     2010-10-14
_journal_date_accepted     2010-10-29
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue     12
_journal_page_first     o3048
_journal_page_last     o3048
_journal_paper_category     QO
_journal_coeditor_code     CV2777
_publ_contact_author_name     'Ming-zhi Song'
_publ_contact_author_address
;
College of Chemistry and Chemical Technology;
Binzhou University; Binzhou 256600;
Shandong; China
;
_publ_contact_author_email     fanchuangang2009@163.com
_publ_contact_author_fax     '86 543 8230686'
_publ_contact_author_phone     '86 543 8230686'
_publ_section_title
;
1-(2-Hydroxybenzoyl)thiosemicarbazide hemihydrate
;
loop_
    _publ_author_name
    _publ_author_address
    'Ming-zhi Song'
;
College of Chemistry and Chemical Technology
Binzhou University, Binzhou 256600
Shandong, People's Republic of China
;
    'Chuangang Fan'
;
College of Chemistry and Chemical Technology
Binzhou University, Binzhou 256600
Shandong, People's Republic of China
;
