#------------------------------------------------------------------------------
#$Date: 2021-03-17 11:53:00 +0200 (Wed, 17 Mar 2021) $
#$Revision: 263084 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/10/1561077.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_1561077
loop_
_publ_author_name
'Yadav, Priyanka'
'Patel, Vatsa'
'Ballabh, Amar'
_publ_section_title
;
 Role of S…O non-bonded interaction in controlling supramolecular
 assemblies in a new series of 2-aminobenzothiazole based organic salts/
 co-crystals
;
_journal_name_full               'Journal of Solid State Chemistry'
_journal_page_first              231
_journal_page_last               238
_journal_paper_doi               10.1016/j.jssc.2018.04.015
_journal_volume                  263
_journal_year                    2018
_chemical_formula_moiety         'C7 H7 N2 S, C8 H7 O2'
_chemical_formula_sum            'C15 H14 N2 O2 S'
_chemical_formula_weight         286.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 113.798(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5590(7)
_cell_length_b                   10.7188(5)
_cell_length_c                   12.1113(7)
_cell_measurement_reflns_used    2807
_cell_measurement_temperature    293
_cell_measurement_theta_max      28.2660
_cell_measurement_theta_min      3.6770
_cell_volume                     1372.99(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0851
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   12.00   38.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2013  -38.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -53.00    8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2013  -38.0000    0.0000 61

#__ type_ start__ end____ width___ exp.time_
  3 omega  -50.00   72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2013    0.0000   30.0000 122

#__ type_ start__ end____ width___ exp.time_
  4 omega  -96.00  -59.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.8263  178.0000   30.0000 37
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0390375000
_diffrn_orient_matrix_UB_12      0.0042812000
_diffrn_orient_matrix_UB_13      0.0323734000
_diffrn_orient_matrix_UB_21      -0.0518403000
_diffrn_orient_matrix_UB_22      -0.0235659000
_diffrn_orient_matrix_UB_23      -0.0508568000
_diffrn_orient_matrix_UB_31      0.0169434000
_diffrn_orient_matrix_UB_32      -0.0616935000
_diffrn_orient_matrix_UB_33      0.0215933000
_diffrn_radiation_collimation    0.8
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    Mo
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5769
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         3.393
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Enhance (Mo) X-ray source'
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68634
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dull white'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_description
;
;
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.866
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2692
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.866
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0380
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0660P)²+0.7121P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1064
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2315
_reflns_number_total             2692
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            JSSC-2018-263-231.cif
_cod_data_source_block           BTzA11
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the built-in table derived from the CIF
Core dictionary named 'cif_core.dic' version 2.4.5 last updated on
2014-11-21.

Automatic conversion script
Id: cif_fix_values 8369 2020-08-20 11:38:08Z andrius 
;
_cod_original_cell_volume        1372.97(14)
_cod_database_code               1561077
_chemical_oxdiff_formula         'C H N O S'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_reflns_odcompleteness_completeness 99.53
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C12(H12), C13(H13), C14(H14), C4(H4), C16(H16), C7(H7)
2.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S9 S 0.07083(4) 0.06147(4) 0.28662(4) 0.03527(16) Uani 1 1 d . . . . .
C8 C 0.14696(16) 0.04449(16) 0.18813(15) 0.0303(4) Uani 1 1 d . . . . .
O19 O 0.15235(13) 0.64323(12) 0.07992(12) 0.0409(3) Uani 1 1 d . . . . .
O18 O 0.26079(13) 0.61612(13) -0.03366(12) 0.0446(4) Uani 1 1 d . . . . .
C17 C 0.23098(16) 0.58419(16) 0.05056(15) 0.0311(4) Uani 1 1 d . . . . .
N10 N -0.12822(16) 0.21734(16) 0.20570(16) 0.0396(4) Uani 1 1 d . . . . .
C6 C 0.29146(18) -0.03274(18) 0.11042(19) 0.0410(5) Uani 1 1 d . . . . .
H6 H 0.3589 -0.0838 0.1169 0.049 Uiso 1 1 calc R . . . .
C5 C 0.23453(18) 0.04121(18) 0.00891(18) 0.0395(4) Uani 1 1 d . . . . .
H5 H 0.2645 0.0386 -0.0517 0.047 Uiso 1 1 calc R . . . .
C12 C 0.2598(2) 0.42288(17) 0.21143(17) 0.0392(4) Uani 1 1 d . . . . .
H12 H 0.1991 0.4637 0.2302 0.047 Uiso 1 1 calc R . . . .
C1 C -0.03479(16) 0.16633(16) 0.18670(15) 0.0306(4) Uani 1 1 d . . . . .
C13 C 0.3187(2) 0.31693(18) 0.27483(18) 0.0454(5) Uani 1 1 d . . . . .
H13 H 0.2982 0.2877 0.3370 0.055 Uiso 1 1 calc R . . . .
C15 C 0.43828(16) 0.29510(17) 0.15276(17) 0.0376(4) Uani 1 1 d . . . . .
C14 C 0.40753(19) 0.25445(18) 0.24644(18) 0.0424(5) Uani 1 1 d . . . . .
H14 H 0.4473 0.1843 0.2906 0.051 Uiso 1 1 calc R . . . .
C4 C 0.13402(17) 0.11896(17) -0.00432(16) 0.0355(4) Uani 1 1 d . . . . .
H4 H 0.0971 0.1692 -0.0722 0.043 Uiso 1 1 calc R . . . .
C3 C 0.09024(15) 0.11967(15) 0.08657(15) 0.0285(4) Uani 1 1 d . . . . .
C16 C 0.38020(16) 0.40248(17) 0.09091(17) 0.0351(4) Uani 1 1 d . . . . .
H16 H 0.4007 0.4315 0.0287 0.042 Uiso 1 1 calc R . . . .
C11 C 0.29158(16) 0.46798(16) 0.12002(15) 0.0311(4) Uani 1 1 d . . . . .
N2 N -0.01088(13) 0.18848(14) 0.08968(13) 0.0310(3) Uani 1 1 d . . . . .
C7 C 0.24926(17) -0.03148(17) 0.20197(18) 0.0367(4) Uani 1 1 d . . . . .
H7 H 0.2881 -0.0800 0.2708 0.044 Uiso 1 1 calc R . . . .
C20 C 0.53027(19) 0.2219(2) 0.1186(2) 0.0530(6) Uani 1 1 d . . . . .
H20A H 0.6029 0.2004 0.1902 0.079 Uiso 1 1 calc GR . . . .
H20B H 0.5563 0.2716 0.0667 0.079 Uiso 1 1 calc GR . . . .
H20C H 0.4902 0.1471 0.0771 0.079 Uiso 1 1 calc GR . . . .
H10A H -0.140(2) 0.193(2) 0.269(2) 0.050(6) Uiso 1 1 d . . . . .
H1 H -0.057(2) 0.247(2) 0.033(2) 0.052(6) Uiso 1 1 d . . . . .
H10B H -0.178(2) 0.270(2) 0.149(2) 0.062(7) Uiso 1 1 d . . . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 S9 C8 89.87(8) . .
C3 C8 S9 110.72(13) . .
C7 C8 S9 127.95(14) . .
C7 C8 C3 121.33(16) . .
O19 C17 C11 118.63(15) . .
O18 C17 O19 123.80(17) . .
O18 C17 C11 117.57(16) . .
C7 C6 C5 120.80(18) . .
C6 C5 C4 121.51(17) . .
C11 C12 C13 119.93(18) . .
N10 C1 S9 122.95(14) . .
N10 C1 N2 124.00(17) . .
N2 C1 S9 113.05(13) . .
C14 C13 C12 120.53(18) . .
C14 C15 C16 118.23(18) . .
C14 C15 C20 120.16(18) . .
C16 C15 C20 121.60(18) . .
C13 C14 C15 120.83(18) . .
C3 C4 C5 118.01(17) . .
C8 C3 N2 112.50(15) . .
C4 C3 C8 120.39(16) . .
C4 C3 N2 127.09(16) . .
C15 C16 C11 121.56(17) . .
C12 C11 C17 121.35(16) . .
C12 C11 C16 118.87(17) . .
C16 C11 C17 119.76(16) . .
C1 N2 C3 113.81(15) . .
C6 C7 C8 117.94(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S9 C8 1.7544(17) .
S9 C1 1.7395(18) .
C8 C3 1.393(2) .
C8 C7 1.389(2) .
O19 C17 1.270(2) .
O18 C17 1.249(2) .
C17 C11 1.508(2) .
N10 C1 1.311(2) .
C6 C5 1.386(3) .
C6 C7 1.380(3) .
C5 C4 1.386(3) .
C12 C13 1.386(3) .
C12 C11 1.386(2) .
C1 N2 1.332(2) .
C13 C14 1.380(3) .
C15 C14 1.389(3) .
C15 C16 1.389(3) .
C15 C20 1.507(3) .
C4 C3 1.385(2) .
C3 N2 1.395(2) .
C16 C11 1.399(2) .
