#------------------------------------------------------------------------------
#$Date: 2019-11-23 21:06:13 +0200 (Sat, 23 Nov 2019) $
#$Revision: 235000 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/66/4036634.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4036634
loop_
_publ_author_name
'Dar, Ajaz A.'
'Shadab, M.'
'Khan, Suman'
'Ali, Nahid'
'Khan, Abu T.'
_publ_section_title
;
 One-Pot Synthesis and Evaluation of Antileishmanial Activities of
 Functionalized S-Alkyl/Aryl Benzothiazole-2-carbothioate Scaffold.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3149
_journal_page_last               3160
_journal_paper_doi               10.1021/acs.joc.6b00113
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C15 H10 Cl N O S2'
_chemical_formula_sum            'C15 H10 Cl N O S2'
_chemical_formula_weight         319.81
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.930(8)
_cell_angle_beta                 96.487(7)
_cell_angle_gamma                93.239(8)
_cell_formula_units_Z            2
_cell_length_a                   8.1250(7)
_cell_length_b                   8.2239(9)
_cell_length_c                   10.6956(8)
_cell_measurement_reflns_used    1496
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.9180
_cell_measurement_theta_min      3.8120
_cell_volume                     708.78(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_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  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0441
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4749
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.99
_exptl_absorpt_coefficient_mu    0.557
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'face installed'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.56
_exptl_crystal_size_min          0.43
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2495
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0407
_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)+(0.0504P)²+0.0136P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.1152
_reflns_number_gt                1891
_reflns_number_total             2495
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b00113_si_003.cif
_cod_data_source_block           ad-145
_cod_original_cell_volume        708.77(11)
_cod_original_sg_symbol_H-M      p-1
_cod_database_code               4036634
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.68020(8) 0.30229(10) 0.66096(6) 0.0530(3) Uani 1 1 d .
S2 S 0.62388(9) 0.07160(9) 0.28923(6) 0.0510(2) Uani 1 1 d .
Cl1 Cl 0.68112(10) 0.13040(13) -0.02023(7) 0.0785(3) Uani 1 1 d .
O1 O 0.8610(2) 0.1265(3) 0.47839(17) 0.0660(7) Uani 1 1 d .
N1 N 0.4487(2) 0.2439(3) 0.47526(18) 0.0417(5) Uani 1 1 d .
C6 C 0.3784(3) 0.3270(3) 0.5678(2) 0.0404(6) Uani 1 1 d .
C1 C 0.4855(3) 0.3691(3) 0.6765(2) 0.0439(7) Uani 1 1 d .
C7 C 0.6038(3) 0.2257(3) 0.5132(2) 0.0391(6) Uani 1 1 d .
C10 C 0.9180(3) 0.0947(3) 0.1751(2) 0.0443(7) Uani 1 1 d .
C8 C 0.7175(3) 0.1422(3) 0.4372(2) 0.0435(7) Uani 1 1 d .
C9 C 0.7990(4) -0.0219(4) 0.2320(3) 0.0623(9) Uani 1 1 d .
H9A H 0.8594 -0.0757 0.3013 0.075 Uiso 1 1 calc R
H9B H 0.7571 -0.1049 0.1691 0.075 Uiso 1 1 calc R
C11 C 0.8778(3) 0.1666(3) 0.0600(2) 0.0439(6) Uani 1 1 d .
C12 C 0.9910(4) 0.2677(4) 0.0070(2) 0.0537(8) Uani 1 1 d .
H12 H 0.9623 0.3125 -0.0712 0.064 Uiso 1 1 calc R
C13 C 1.1457(4) 0.3018(4) 0.0698(3) 0.0638(9) Uani 1 1 d .
H13 H 1.2220 0.3703 0.0345 0.077 Uiso 1 1 calc R
C3 C 0.2663(4) 0.4912(4) 0.7649(3) 0.0674(10) Uani 1 1 d .
H3 H 0.2268 0.5477 0.8303 0.081 Uiso 1 1 calc R
C15 C 1.0758(4) 0.1323(4) 0.2363(3) 0.0566(9) Uani 1 1 d .
H15 H 1.1062 0.0869 0.3140 0.068 Uiso 1 1 calc R
C5 C 0.2122(3) 0.3670(4) 0.5592(3) 0.0565(8) Uani 1 1 d .
H5 H 0.1394 0.3383 0.4878 0.068 Uiso 1 1 calc R
C2 C 0.4299(4) 0.4516(4) 0.7768(3) 0.0588(8) Uani 1 1 d .
H2 H 0.5007 0.4791 0.8495 0.071 Uiso 1 1 calc R
C4 C 0.1594(4) 0.4488(4) 0.6576(3) 0.0655(10) Uani 1 1 d .
H4 H 0.0495 0.4767 0.6527 0.079 Uiso 1 1 calc R
C14 C 1.1884(4) 0.2350(4) 0.1852(3) 0.0662(9) Uani 1 1 d .
H14 H 1.2930 0.2593 0.2284 0.079 Uiso 1 1 calc R
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'
Cl Cl 0.1484 0.1585 '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
C7 S1 C1 88.44(12)
C8 S2 C9 99.49(14)
C7 N1 C6 109.2(2)
N1 C6 C1 115.3(2)
N1 C6 C5 124.8(3)
C1 C6 C5 119.9(2)
C2 C1 C6 121.0(2)
C2 C1 S1 129.5(2)
C6 C1 S1 109.54(18)
N1 C7 C8 123.7(2)
N1 C7 S1 117.54(18)
C8 C7 S1 118.75(18)
C15 C10 C11 117.0(3)
C15 C10 C9 120.5(2)
C11 C10 C9 122.4(3)
O1 C8 C7 120.8(3)
O1 C8 S2 125.3(2)
C7 C8 S2 113.88(19)
C10 C9 S2 114.69(18)
C12 C11 C10 121.6(3)
C12 C11 Cl1 118.5(2)
C10 C11 Cl1 119.9(2)
C13 C12 C11 119.8(2)
C12 C13 C14 120.1(3)
C2 C3 C4 121.5(3)
C14 C15 C10 121.8(2)
C4 C5 C6 118.6(3)
C3 C2 C1 117.8(3)
C5 C4 C3 121.2(3)
C15 C14 C13 119.7(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C7 1.727(3)
S1 C1 1.729(2)
S2 C8 1.751(3)
S2 C9 1.815(2)
Cl1 C11 1.734(3)
O1 C8 1.214(3)
N1 C7 1.297(3)
N1 C6 1.387(3)
C6 C1 1.398(4)
C6 C5 1.401(3)
C1 C2 1.391(3)
C7 C8 1.486(3)
C10 C15 1.388(4)
C10 C11 1.388(3)
C10 C9 1.507(4)
C11 C12 1.381(4)
C12 C13 1.369(4)
C13 C14 1.375(4)
C3 C2 1.379(4)
C3 C4 1.386(4)
C15 C14 1.375(4)
C5 C4 1.362(4)
