##############################################################################
# #
# 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 2011-11-14
_journal_date_accepted 2011-11-26
_journal_name_full 'Acta Crystallographica, Section E'
_journal_year 2011
_journal_volume 67
_journal_issue 12
_journal_page_first o3518
_journal_page_last o3518
_journal_paper_category QO
_journal_paper_doi 10.1107/S1600536811050902
_journal_coeditor_code FJ2484
_publ_contact_author_name 'Dr. Kargar, Hadi'
_publ_contact_author_address
;
Department of Chemistry,
Payame Noor University,
PO BOX 19395-3697 Tehran,
Iran
;
_publ_contact_author_email 'hadi_kargar@yahoo.com, hkargar@pnu.ac.ir'
_publ_contact_author_fax ?
_publ_contact_author_phone ?
_publ_section_title
;\
(E)-5-[(2-Hydroxy-3-methoxybenzylidene)amino]-1,3,4-thiadiazole-\
2(3H)-thione
;
loop_
_publ_author_name
_publ_author_address
'Kargar, Hadi'
;
Department of Chemistry,
Payame Noor University,
PO BOX 19395-3697 Tehran,
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
;
data_I
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
(E)-5-[(2-Hydroxy-3-methoxybenzylidene)amino]-
1,3,4-thiadiazole-2(3H)-thione
;
_chemical_name_common
;
;
_chemical_formula_moiety 'C10 H9 N3 O2 S2'
_chemical_formula_sum 'C10 H9 N3 O2 S2'
_chemical_formula_iupac 'C10 H9 N3 O2 S2'
_chemical_formula_weight 267.32
_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 7.432(5)
_cell_length_b 14.993(5)
_cell_length_c 10.853(5)
_cell_angle_alpha 90.0
_cell_angle_beta 101.738(5)
_cell_angle_gamma 90.0
_cell_volume 1184.0(10)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 2780
_cell_measurement_theta_min 2.45
_cell_measurement_theta_max 27.43
_cell_measurement_temperature 291(2)
_exptl_crystal_description block
_exptl_crystal_colour yellow
_exptl_crystal_size_max 0.25
_exptl_crystal_size_mid 0.21
_exptl_crystal_size_min 0.11
_exptl_crystal_density_diffrn 1.500
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 552
_exptl_absorpt_coefficient_mu 0.442
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
[MULABS (Blessing, 1995) in PLATON (Spek, 2009)]
;
_exptl_absorpt_correction_T_min 0.898
_exptl_absorpt_correction_T_max 1.000
_exptl_special_details ?
_diffrn_ambient_temperature 291(2)
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71069
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Stoe IPDS 2T Image Plate'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_reflns_number 9012
_diffrn_reflns_av_R_equivalents 0.0748
_diffrn_reflns_av_sigmaI/netI 0.1135
_diffrn_reflns_theta_min 2.35
_diffrn_reflns_theta_max 29.00
_diffrn_reflns_theta_full 29.00
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_k_min -20
_diffrn_reflns_limit_k_max 19
_diffrn_reflns_limit_l_min -14
_diffrn_reflns_limit_l_max 14
_diffrn_standards_number 0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% ?
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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 3147
_reflns_number_gt 1530
_reflns_threshold_expression I>2\s(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.1511
_refine_ls_R_factor_gt 0.0573
_refine_ls_wR_factor_gt 0.0640
_refine_ls_wR_factor_ref 0.0792
_refine_ls_goodness_of_fit_ref 0.918
_refine_ls_restrained_S_all 0.918
_refine_ls_number_reflns 3147
_refine_ls_number_parameters 155
_refine_ls_number_restraints 0
_refine_ls_hydrogen_treatment constr
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0235P)^2^] where P=(Fo^2^+2Fc^2^)/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 0.207
_refine_diff_density_min -0.216
_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 'X-AREA (Stoe & Cie, 2009)'
_computing_cell_refinement 'X-AREA (Stoe & Cie, 2009)'
_computing_data_reduction 'X-AREA (Stoe & Cie, 2009)'
_computing_structure_solution 'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXTL (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
S S1 0.21750(10) 0.70390(4) 0.52967(6) 0.04780(19) Uani d . 1 1 . .
S S2 0.26803(11) 0.88098(5) 0.66246(8) 0.0669(3) Uani d . 1 1 . .
O O1 0.3794(2) 0.35277(10) 0.59426(14) 0.0493(5) Uani d . 1 1 . .
H H1 0.3815 0.4009 0.6167 0.074 Uiso d R 1 1 . .
O O2 0.3399(3) 0.19524(12) 0.50192(17) 0.0610(5) Uani d . 1 1 . .
N N1 0.3081(3) 0.52471(12) 0.57179(17) 0.0366(5) Uani d . 1 1 . .
N N2 0.4094(3) 0.63027(13) 0.72724(18) 0.0436(5) Uani d . 1 1 . .
N N3 0.3970(3) 0.72004(13) 0.74725(18) 0.0471(6) Uani d . 1 1 . .
H H3 0.4552 0.7361 0.8202 0.056 Uiso d R 1 1 . .
C C1 0.2778(3) 0.34679(16) 0.4758(2) 0.0380(6) Uani d . 1 1 . .
C C2 0.2551(4) 0.26105(18) 0.4235(2) 0.0437(7) Uani d . 1 1 . .
C C3 0.1578(4) 0.2506(2) 0.3031(3) 0.0561(8) Uani d . 1 1 . .
H H3A 0.1432 0.1940 0.2674 0.067 Uiso calc R 1 1 . .
C C4 0.0809(4) 0.3235(2) 0.2342(3) 0.0604(8) Uani d . 1 1 . .
H H4A 0.0156 0.3155 0.1523 0.073 Uiso calc R 1 1 . .
C C5 0.0996(4) 0.40713(18) 0.2846(2) 0.0528(7) Uani d . 1 1 . .
H H5A 0.0462 0.4556 0.2375 0.063 Uiso calc R 1 1 . .
C C6 0.1990(3) 0.41983(17) 0.4071(2) 0.0365(6) Uani d . 1 1 . .
C C7 0.2189(3) 0.50812(16) 0.4597(2) 0.0395(6) Uani d . 1 1 . .
H H7A 0.1647 0.5555 0.4103 0.047 Uiso calc R 1 1 . .
C C8 0.3194(3) 0.61176(16) 0.6153(2) 0.0351(6) Uani d . 1 1 . .
C C9 0.3028(4) 0.77222(16) 0.6575(2) 0.0438(6) Uani d . 1 1 . .
C C10 0.2996(5) 0.10417(18) 0.4652(3) 0.0769(10) Uani d . 1 1 . .
H H10A 0.3550 0.0653 0.5326 0.115 Uiso calc R 1 1 . .
H H10B 0.3481 0.0910 0.3917 0.115 Uiso calc R 1 1 . .
H H10C 0.1690 0.0953 0.4468 0.115 Uiso calc R 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
S1 0.0536(5) 0.0348(4) 0.0529(4) 0.0065(3) 0.0058(3) 0.0043(3)
S2 0.0708(6) 0.0335(4) 0.0980(6) 0.0065(4) 0.0208(5) -0.0043(4)
O1 0.0629(13) 0.0321(10) 0.0487(11) 0.0050(9) 0.0013(9) 0.0003(7)
O2 0.0684(14) 0.0303(11) 0.0841(14) 0.0019(10) 0.0148(11) -0.0055(9)
N1 0.0394(13) 0.0303(12) 0.0397(12) 0.0015(10) 0.0071(10) -0.0017(9)
N2 0.0455(14) 0.0333(13) 0.0497(13) 0.0026(10) 0.0041(11) -0.0036(10)
N3 0.0482(14) 0.0407(14) 0.0499(13) -0.0017(11) 0.0044(11) -0.0094(11)
C1 0.0352(15) 0.0415(15) 0.0389(13) -0.0042(12) 0.0112(12) -0.0040(12)
C2 0.0428(17) 0.0374(16) 0.0540(17) -0.0030(13) 0.0175(14) -0.0048(13)
C3 0.062(2) 0.0465(19) 0.0655(19) -0.0168(15) 0.0269(16) -0.0203(15)
C4 0.067(2) 0.064(2) 0.0484(16) -0.0238(18) 0.0068(15) -0.0136(16)
C5 0.0549(19) 0.0518(19) 0.0478(17) -0.0114(15) 0.0013(14) 0.0021(13)
C6 0.0338(15) 0.0358(15) 0.0399(14) -0.0044(12) 0.0074(12) 0.0008(11)
C7 0.0374(16) 0.0366(16) 0.0449(15) 0.0006(12) 0.0094(13) 0.0077(12)
C8 0.0344(14) 0.0309(14) 0.0414(14) 0.0033(11) 0.0108(12) 0.0054(11)
C9 0.0390(15) 0.0376(15) 0.0578(16) -0.0019(13) 0.0167(13) -0.0025(13)
C10 0.083(3) 0.0348(18) 0.115(3) -0.0048(17) 0.026(2) -0.0109(18)
_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
S1 C9 . 1.737(3) ?
S1 C8 . 1.749(2) ?
S2 C9 . 1.654(3) ?
O1 C1 . 1.355(3) ?
O1 H1 . 0.7607 ?
O2 C2 . 1.370(3) ?
O2 C10 . 1.437(3) ?
N1 C7 . 1.286(3) ?
N1 C8 . 1.385(3) ?
N2 C8 . 1.292(3) ?
N2 N3 . 1.369(3) ?
N3 C9 . 1.332(3) ?
N3 H3 . 0.8561 ?
C1 C6 . 1.386(3) ?
C1 C2 . 1.401(3) ?
C2 C3 . 1.369(3) ?
C3 C4 . 1.381(4) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.364(3) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.397(3) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.437(3) ?
C7 H7A . 0.9300 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
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
C9 S1 C8 . . 89.62(13) ?
C1 O1 H1 . . 109.8 ?
C2 O2 C10 . . 118.0(2) ?
C7 N1 C8 . . 119.3(2) ?
C8 N2 N3 . . 108.7(2) ?
C9 N3 N2 . . 120.2(2) ?
C9 N3 H3 . . 127.1 ?
N2 N3 H3 . . 112.7 ?
O1 C1 C6 . . 123.5(2) ?
O1 C1 C2 . . 116.3(2) ?
C6 C1 C2 . . 120.3(2) ?
C3 C2 O2 . . 126.7(3) ?
C3 C2 C1 . . 119.3(3) ?
O2 C2 C1 . . 114.0(2) ?
C2 C3 C4 . . 120.4(3) ?
C2 C3 H3A . . 119.8 ?
C4 C3 H3A . . 119.8 ?
C5 C4 C3 . . 120.9(3) ?
C5 C4 H4A . . 119.5 ?
C3 C4 H4A . . 119.5 ?
C4 C5 C6 . . 119.9(3) ?
C4 C5 H5A . . 120.1 ?
C6 C5 H5A . . 120.1 ?
C1 C6 C5 . . 119.2(2) ?
C1 C6 C7 . . 121.1(2) ?
C5 C6 C7 . . 119.7(2) ?
N1 C7 C6 . . 123.0(2) ?
N1 C7 H7A . . 118.5 ?
C6 C7 H7A . . 118.5 ?
N2 C8 N1 . . 120.5(2) ?
N2 C8 S1 . . 114.54(18) ?
N1 C8 S1 . . 125.01(18) ?
N3 C9 S2 . . 128.1(2) ?
N3 C9 S1 . . 106.85(18) ?
S2 C9 S1 . . 125.01(17) ?
O2 C10 H10A . . 109.5 ?
O2 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
O2 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
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
C8 N2 N3 C9 . . . . 0.0(3) ?
C10 O2 C2 C3 . . . . -11.4(4) ?
C10 O2 C2 C1 . . . . 169.9(2) ?
O1 C1 C2 C3 . . . . -178.4(2) ?
C6 C1 C2 C3 . . . . 1.3(4) ?
O1 C1 C2 O2 . . . . 0.4(3) ?
C6 C1 C2 O2 . . . . -179.9(2) ?
O2 C2 C3 C4 . . . . -179.3(3) ?
C1 C2 C3 C4 . . . . -0.7(4) ?
C2 C3 C4 C5 . . . . -0.3(4) ?
C3 C4 C5 C6 . . . . 0.6(4) ?
O1 C1 C6 C5 . . . . 178.7(2) ?
C2 C1 C6 C5 . . . . -1.0(4) ?
O1 C1 C6 C7 . . . . -1.0(4) ?
C2 C1 C6 C7 . . . . 179.3(2) ?
C4 C5 C6 C1 . . . . 0.1(4) ?
C4 C5 C6 C7 . . . . 179.8(2) ?
C8 N1 C7 C6 . . . . -179.6(2) ?
C1 C6 C7 N1 . . . . -0.5(4) ?
C5 C6 C7 N1 . . . . 179.8(2) ?
N3 N2 C8 N1 . . . . -179.1(2) ?
N3 N2 C8 S1 . . . . 0.5(2) ?
C7 N1 C8 N2 . . . . -179.5(2) ?
C7 N1 C8 S1 . . . . 1.0(3) ?
C9 S1 C8 N2 . . . . -0.61(19) ?
C9 S1 C8 N1 . . . . 178.9(2) ?
N2 N3 C9 S2 . . . . 179.02(18) ?
N2 N3 C9 S1 . . . . -0.4(3) ?
C8 S1 C9 N3 . . . . 0.53(18) ?
C8 S1 C9 S2 . . . . -178.93(18) ?
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 . 0.7600 1.9700 2.633(3) 146.00 y
N3 H3 O1 2_656 0.8600 2.2300 2.919(3) 138.00 y
N3 H3 O2 2_656 0.8600 2.2900 3.034(3) 146.00 y