##############################################################################
# #
# 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 2011-11-13
_journal_date_accepted 2011-11-21
_journal_name_full 'Acta Crystallographica, Section E'
_journal_year 2011
_journal_volume 67
_journal_issue 12
_journal_page_first o3436
_journal_page_last o3436
_journal_paper_category QO
_journal_coeditor_code LH5379
loop_
_publ_contact_author_name
_publ_contact_author_address
_publ_contact_author_email
'Prof. Tahir, Muhammad Nawaz '
;
Department of Physics
University of Sargodha
Punjab, Pakistan
;
dmntahir_uos@yahoo.com
'Kia, Reza'
;
X-ray Crystallography Laboratory,
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
;
zsrkk@yahoo.com
_publ_contact_author_fax ?
_publ_contact_author_phone ?
_publ_section_title
;\
5-[(E)-(5-Bromo-2-hydroxybenzylidene)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 Laboratory,
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
;
5-[(E)-(5-bromo-2-hydroxybenzylidene)amino]-
1,3,4-thiadiazole-2(3H)-thione
;
_chemical_name_common
;
;
_chemical_formula_moiety 'C9 H6 Br N3 O S2'
_chemical_formula_sum 'C9 H6 Br N3 O S2'
_chemical_formula_iupac 'C9 H6 Br N3 O S2'
_chemical_formula_weight 316.20
_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 18.3690(13)
_cell_length_b 4.0016(3)
_cell_length_c 16.2877(13)
_cell_angle_alpha 90.00
_cell_angle_beta 112.660(4)
_cell_angle_gamma 90.00
_cell_volume 1104.82(14)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 2573
_cell_measurement_theta_min 2.50
_cell_measurement_theta_max 29.31
_cell_measurement_temperature 291(2)
_exptl_crystal_description block
_exptl_crystal_colour yellow
_exptl_crystal_size_max 0.11
_exptl_crystal_size_mid 0.05
_exptl_crystal_size_min 0.02
_exptl_crystal_density_diffrn 1.901
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 624
_exptl_absorpt_coefficient_mu 4.078
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min 0.6626
_exptl_absorpt_correction_T_max 0.9229
_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 '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 2734
_diffrn_reflns_av_R_equivalents 0.0707
_diffrn_reflns_av_sigmaI/netI 0.0778
_diffrn_reflns_theta_min 1.20
_diffrn_reflns_theta_max 28.27
_diffrn_reflns_theta_full 28.27
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_limit_h_min -24
_diffrn_reflns_limit_h_max 24
_diffrn_reflns_limit_k_min -5
_diffrn_reflns_limit_k_max 5
_diffrn_reflns_limit_l_min -21
_diffrn_reflns_limit_l_max 21
_diffrn_standards_number 0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_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 10313
_reflns_number_gt 1760
_reflns_threshold_expression I>2\s(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.1087
_refine_ls_R_factor_gt 0.0597
_refine_ls_wR_factor_gt 0.1248
_refine_ls_wR_factor_ref 0.1398
_refine_ls_goodness_of_fit_ref 1.079
_refine_ls_restrained_S_all 1.079
_refine_ls_number_reflns 2734
_refine_ls_number_parameters 147
_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^)+(0.0412P)^2^+3.7473P] 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 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 1.245
_refine_diff_density_min -0.709
_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'
'Br' 'Br' -0.2901 2.4595
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection 'APEX2 (Bruker, 2005)'
_computing_cell_refinement 'APEX2 (Bruker, 2005)'
_computing_data_reduction 'SAINT (Bruker, 2005)'
_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
Br Br1 0.65016(4) 0.82937(19) -0.22477(5) 0.0438(2) Uani d . 1 1 . .
S S1 0.92727(8) 0.4125(4) 0.25824(11) 0.0306(4) Uani d . 1 1 . .
S S2 1.06396(9) 0.3421(4) 0.43539(10) 0.0329(4) Uani d . 1 1 . .
O O1 0.6140(2) 0.1515(13) 0.0870(3) 0.0439(12) Uani d . 1 1 . .
H H1 0.6563 0.1408 0.1296 0.066 Uiso calc R 1 1 . .
N N1 0.7683(3) 0.2398(13) 0.1762(3) 0.0314(12) Uani d . 1 1 . .
N N2 0.8404(3) 0.0884(14) 0.3226(4) 0.0355(13) Uani d . 1 1 . .
N N3 0.9159(3) 0.1150(13) 0.3865(3) 0.0347(13) Uani d . 1 1 . .
H H3 0.9211 -0.0002 0.4408 0.042 Uiso d R 1 1 . .
C C1 0.6244(3) 0.3022(18) 0.0192(4) 0.0340(15) Uani d . 1 1 . .
C C2 0.6990(3) 0.4180(15) 0.0246(4) 0.0286(13) Uani d . 1 1 . .
C C3 0.7065(3) 0.5752(15) -0.0484(4) 0.0315(14) Uani d . 1 1 . .
H H3A 0.7556 0.6477 -0.0453 0.038 Uiso calc R 1 1 . .
C C4 0.6402(3) 0.6216(15) -0.1255(4) 0.0313(14) Uani d . 1 1 . .
C C5 0.5670(4) 0.5144(17) -0.1308(4) 0.0365(15) Uani d . 1 1 . .
H H5A 0.5229 0.5488 -0.1829 0.044 Uiso calc R 1 1 . .
C C6 0.5587(3) 0.3570(17) -0.0598(4) 0.0367(15) Uani d . 1 1 . .
H H6A 0.5091 0.2864 -0.0642 0.044 Uiso calc R 1 1 . .
C C7 0.7688(3) 0.3839(16) 0.1055(4) 0.0339(15) Uani d . 1 1 . .
H H7A 0.8162 0.4697 0.1066 0.041 Uiso calc R 1 1 . .
C C8 0.8377(3) 0.2352(15) 0.2507(4) 0.0260(13) Uani d . 1 1 . .
C C9 0.9707(3) 0.2737(14) 0.3678(4) 0.0261(13) 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
Br1 0.0511(4) 0.0493(4) 0.0304(4) 0.0088(3) 0.0152(3) 0.0084(3)
S1 0.0242(7) 0.0387(9) 0.0263(8) -0.0014(6) 0.0067(6) 0.0065(7)
S2 0.0252(7) 0.0429(9) 0.0264(9) -0.0014(7) 0.0055(6) -0.0007(7)
O1 0.030(2) 0.065(3) 0.033(3) -0.009(2) 0.008(2) 0.008(3)
N1 0.026(3) 0.039(3) 0.026(3) 0.002(2) 0.006(2) 0.001(2)
N2 0.024(2) 0.051(3) 0.029(3) -0.006(2) 0.006(2) 0.003(3)
N3 0.033(3) 0.047(3) 0.024(3) -0.005(2) 0.010(2) 0.006(3)
C1 0.029(3) 0.053(4) 0.024(3) -0.008(3) 0.014(3) -0.004(3)
C2 0.027(3) 0.031(3) 0.026(3) 0.001(2) 0.008(3) 0.001(3)
C3 0.024(3) 0.041(4) 0.028(3) 0.002(3) 0.008(3) 0.000(3)
C4 0.033(3) 0.032(3) 0.026(3) 0.001(3) 0.007(3) 0.003(3)
C5 0.033(3) 0.044(4) 0.025(3) 0.003(3) 0.003(3) -0.002(3)
C6 0.024(3) 0.045(4) 0.037(4) -0.003(3) 0.008(3) 0.001(3)
C7 0.023(3) 0.042(4) 0.034(4) 0.002(3) 0.007(3) -0.001(3)
C8 0.021(3) 0.033(3) 0.023(3) 0.003(2) 0.007(2) 0.003(2)
C9 0.032(3) 0.026(3) 0.021(3) 0.002(2) 0.010(3) -0.003(2)
_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
Br1 C4 . 1.889(6) ?
S1 C9 . 1.741(6) ?
S1 C8 . 1.752(6) ?
S2 C9 . 1.663(6) ?
O1 C1 . 1.334(7) ?
O1 H1 . 0.8200 ?
N1 C7 . 1.292(8) ?
N1 C8 . 1.381(7) ?
N2 C8 . 1.293(8) ?
N2 N3 . 1.381(7) ?
N3 C9 . 1.322(8) ?
N3 H3 . 0.9690 ?
C1 C6 . 1.402(8) ?
C1 C2 . 1.417(8) ?
C2 C3 . 1.399(8) ?
C2 C7 . 1.448(8) ?
C3 C4 . 1.384(8) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.382(9) ?
C5 C6 . 1.377(9) ?
C5 H5A . 0.9300 ?
C6 H6A . 0.9300 ?
C7 H7A . 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
C9 S1 C8 . . 89.4(3) ?
C1 O1 H1 . . 109.5 ?
C7 N1 C8 . . 117.9(5) ?
C8 N2 N3 . . 108.9(5) ?
C9 N3 N2 . . 119.8(5) ?
C9 N3 H3 . . 128.5 ?
N2 N3 H3 . . 111.7 ?
O1 C1 C6 . . 118.9(5) ?
O1 C1 C2 . . 122.7(6) ?
C6 C1 C2 . . 118.4(6) ?
C3 C2 C1 . . 120.3(6) ?
C3 C2 C7 . . 118.2(5) ?
C1 C2 C7 . . 121.5(6) ?
C4 C3 C2 . . 119.4(5) ?
C4 C3 H3A . . 120.3 ?
C2 C3 H3A . . 120.3 ?
C5 C4 C3 . . 120.8(6) ?
C5 C4 Br1 . . 119.7(5) ?
C3 C4 Br1 . . 119.6(5) ?
C6 C5 C4 . . 120.6(6) ?
C6 C5 H5A . . 119.7 ?
C4 C5 H5A . . 119.7 ?
C5 C6 C1 . . 120.6(6) ?
C5 C6 H6A . . 119.7 ?
C1 C6 H6A . . 119.7 ?
N1 C7 C2 . . 123.0(6) ?
N1 C7 H7A . . 118.5 ?
C2 C7 H7A . . 118.5 ?
N2 C8 N1 . . 120.1(5) ?
N2 C8 S1 . . 114.4(4) ?
N1 C8 S1 . . 125.5(5) ?
N3 C9 S2 . . 127.4(5) ?
N3 C9 S1 . . 107.5(4) ?
S2 C9 S1 . . 125.1(4) ?
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 . . . . 0.2(8) ?
O1 C1 C2 C3 . . . . -179.9(6) ?
C6 C1 C2 C3 . . . . -1.7(10) ?
O1 C1 C2 C7 . . . . -1.1(10) ?
C6 C1 C2 C7 . . . . 177.1(6) ?
C1 C2 C3 C4 . . . . 1.1(9) ?
C7 C2 C3 C4 . . . . -177.7(6) ?
C2 C3 C4 C5 . . . . -0.1(9) ?
C2 C3 C4 Br1 . . . . -179.3(5) ?
C3 C4 C5 C6 . . . . -0.4(10) ?
Br1 C4 C5 C6 . . . . 178.8(5) ?
C4 C5 C6 C1 . . . . -0.1(10) ?
O1 C1 C6 C5 . . . . 179.4(6) ?
C2 C1 C6 C5 . . . . 1.2(10) ?
C8 N1 C7 C2 . . . . -177.1(5) ?
C3 C2 C7 N1 . . . . -179.2(6) ?
C1 C2 C7 N1 . . . . 1.9(10) ?
N3 N2 C8 N1 . . . . 179.3(5) ?
N3 N2 C8 S1 . . . . -0.1(7) ?
C7 N1 C8 N2 . . . . -178.7(6) ?
C7 N1 C8 S1 . . . . 0.6(8) ?
C9 S1 C8 N2 . . . . 0.0(5) ?
C9 S1 C8 N1 . . . . -179.3(5) ?
N2 N3 C9 S2 . . . . 178.3(5) ?
N2 N3 C9 S1 . . . . -0.2(7) ?
C8 S1 C9 N3 . . . . 0.1(5) ?
C8 S1 C9 S2 . . . . -178.4(4) ?
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 1.94 2.664(7) 147 y
N3 H3 S2 3_756 0.97 2.36 3.327(5) 173 y