#------------------------------------------------------------------------------
#$Date: 2019-11-23 21:05:50 +0200 (Sat, 23 Nov 2019) $
#$Revision: 234998 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/66/4036633.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_4036633
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 H11 N O S2'
_chemical_formula_sum            'C15 H11 N O S2'
_chemical_formula_weight         285.37
_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                87.223(8)
_cell_angle_beta                 88.919(9)
_cell_angle_gamma                85.132(9)
_cell_formula_units_Z            2
_cell_length_a                   5.6221(11)
_cell_length_b                   9.6836(17)
_cell_length_c                   12.619(2)
_cell_measurement_reflns_used    2043
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.99
_cell_measurement_theta_min      2.72
_cell_volume                     683.6(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0510
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4468
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         1.62
_exptl_absorpt_coefficient_mu    0.379
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.502
_refine_diff_density_min         -1.095
_refine_diff_density_rms         0.132
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         1960
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.148
_refine_ls_R_factor_all          0.1511
_refine_ls_R_factor_gt           0.0796
_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)+(0.0500P)²+3.6000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1883
_refine_ls_wR_factor_ref         0.2469
_reflns_number_gt                1522
_reflns_number_total             2428
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b00113_si_002.cif
_cod_data_source_block           ad-131_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        683.7(2)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4036633
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 0.3690(5) 1.0166(2) 0.25160(17) 0.0658(8) Uani 1 1 d .
S2 S 0.9626(5) 0.6973(2) 0.28187(18) 0.0730(9) Uani 1 1 d .
C4 C 0.9627(19) 0.5440(9) 0.2107(6) 0.061(3) Uani 1 1 d .
C3 C 1.1536(18) 0.5101(9) 0.1420(7) 0.064(3) Uani 1 1 d .
H3 H 1.2760 0.5686 0.1321 0.077 Uiso 1 1 calc R
C1 C 0.9769(19) 0.3008(8) 0.0997(7) 0.060(3) Uani 1 1 d .
C6 C 0.7874(19) 0.3364(9) 0.1689(8) 0.069(3) Uani 1 1 d .
H6 H 0.6636 0.2788 0.1779 0.082 Uiso 1 1 calc R
C5 C 0.7819(17) 0.4571(9) 0.2244(7) 0.066(3) Uani 1 1 d .
H5 H 0.6556 0.4793 0.2709 0.079 Uiso 1 1 calc R
C2 C 1.1583(17) 0.3871(9) 0.0881(6) 0.062(3) Uani 1 1 d .
H2 H 1.2871 0.3631 0.0435 0.074 Uiso 1 1 calc R
C7 C 0.6995(17) 0.7915(8) 0.2319(6) 0.061(3) Uani 1 1 d .
O1 O 0.5780(11) 0.7538(6) 0.1625(5) 0.0732(19) Uani 1 1 d .
N1 N 0.7581(13) 0.9679(7) 0.3607(5) 0.059(2) Uani 1 1 d .
C8 C 0.6365(15) 0.9214(8) 0.2865(6) 0.054(2) Uani 1 1 d .
C10 C 0.4226(17) 1.1331(9) 0.3474(6) 0.061(3) Uani 1 1 d .
C9 C 0.6397(17) 1.0903(9) 0.3978(6) 0.062(3) Uani 1 1 d .
C11 C 0.2868(19) 1.2524(9) 0.3749(7) 0.073(3) Uani 1 1 d .
H11 H 0.1447 1.2813 0.3409 0.088 Uiso 1 1 calc R
C14 C 0.7206(19) 1.1662(9) 0.4787(7) 0.071(3) Uani 1 1 d .
H14 H 0.8625 1.1384 0.5133 0.085 Uiso 1 1 calc R
C12 C 0.3703(19) 1.3255(10) 0.4538(7) 0.076(3) Uani 1 1 d .
H12 H 0.2823 1.4060 0.4739 0.091 Uiso 1 1 calc R
C13 C 0.583(2) 1.2836(10) 0.5054(7) 0.075(3) Uani 1 1 d .
H13 H 0.6335 1.3364 0.5590 0.090 Uiso 1 1 calc R
C15 C 0.974(2) 0.1721(9) 0.0373(7) 0.089(3) Uani 1 1 d .
H15A H 0.8927 0.1035 0.0780 0.133 Uiso 1 1 calc R
H15B H 1.1347 0.1361 0.0224 0.133 Uiso 1 1 calc R
H15C H 0.8920 0.1947 -0.0281 0.133 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C10 S1 C8 88.6(4)
C4 S2 C7 100.4(4)
C5 C4 C3 120.0(9)
C5 C4 S2 121.2(9)
C3 C4 S2 118.8(7)
C4 C3 C2 119.0(8)
C2 C1 C6 118.6(8)
C2 C1 C15 121.8(10)
C6 C1 C15 119.5(8)
C5 C6 C1 120.6(8)
C4 C5 C6 120.2(10)
C1 C2 C3 121.5(9)
O1 C7 C8 122.2(8)
O1 C7 S2 124.8(7)
C8 C7 S2 113.0(5)
C8 N1 C9 109.9(7)
N1 C8 C7 125.4(8)
N1 C8 S1 117.2(7)
C7 C8 S1 117.4(6)
C11 C10 C9 121.4(8)
C11 C10 S1 129.1(7)
C9 C10 S1 109.5(7)
C14 C9 N1 124.8(9)
C14 C9 C10 120.3(9)
N1 C9 C10 114.8(7)
C12 C11 C10 117.2(9)
C13 C14 C9 117.5(9)
C11 C12 C13 122.1(10)
C14 C13 C12 121.4(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C10 1.740(8)
S1 C8 1.748(9)
S2 C4 1.772(9)
S2 C7 1.780(9)
C4 C5 1.377(12)
C4 C3 1.395(13)
C3 C2 1.398(11)
C1 C2 1.374(11)
C1 C6 1.396(13)
C1 C15 1.507(11)
C6 C5 1.390(12)
C7 O1 1.210(8)
C7 C8 1.477(11)
N1 C8 1.290(9)
N1 C9 1.405(11)
C10 C11 1.384(12)
C10 C9 1.408(12)
C9 C14 1.392(10)
C11 C12 1.362(11)
C14 C13 1.371(13)
C12 C13 1.395(13)
