#------------------------------------------------------------------------------
#$Date: 2017-05-05 02:26:47 +0300 (Fri, 05 May 2017) $
#$Revision: 196194 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/24/4032475.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_4032475
loop_
_publ_author_name
'Langis-Barsetti, Sophie'
'Maris, Thierry'
'Wuest, James D.'
_publ_section_title
;
 Molecular Organization of 2,1,3-Benzothiadiazoles in the Solid State.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.6b02778
_journal_year                    2017
_chemical_formula_moiety         'C6 N6 S3'
_chemical_formula_sum            'C6 N6 S3'
_chemical_formula_weight         252.30
_space_group_crystal_system      orthorhombic
_space_group_IT_number           31
_space_group_name_Hall           'P 2ac -2'
_space_group_name_H-M_alt        'P m n 21'
_symmetry_space_group_name_Hall  'P 2ac -2'
_symmetry_space_group_name_H-M   'P m n 21'
_atom_sites_solution_primary     direct
_audit_creation_date             2016-10-29
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.218(2)
_cell_length_b                   3.6510(7)
_cell_length_c                   7.7954(13)
_cell_measurement_reflns_used    2474
_cell_measurement_temperature    100
_cell_measurement_theta_max      60.565
_cell_measurement_theta_min      5.415
_cell_volume                     404.66(12)
_computing_cell_refinement
;
SAINT (2013) V8.34A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction
;
SAINT (2013) V8.34A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_av_unetI/netI     0.0581
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3851
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.707
_diffrn_reflns_theta_min         5.414
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_exptl_absorpt_coefficient_mu    5.384
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.5586
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1329 before and 0.0806 after correction.
The Ratio of minimum to maximum transmission is 0.7429.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.071
_exptl_crystal_description       Needle
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.015
_exptl_crystal_size_min          0.015
_refine_diff_density_max         0.512
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.110
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.08(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     71
_refine_ls_number_reflns         910
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0387
_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)+(0.0556P)²+0.0335P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.0979
_reflns_Friedel_coverage         0.865
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                846
_reflns_number_total             910
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo6b02778_si_004.cif
_cod_data_source_block           jw1814
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               4032475
_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.
;
_shelx_estimated_absorpt_t_max   0.924
_shelx_estimated_absorpt_t_min   0.222
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.92(7) 0.08(7)
;
_shelx_shelxl_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y, z+1/2'
'-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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
S1 S 0.500000 0.3778(4) 0.15094(17) 0.0193(4) Uani 1 2 d S T P
S2 S 0.71491(7) 0.8882(3) 0.78586(16) 0.0193(3) Uani 1 1 d . . .
N1 N 0.5880(2) 0.4786(11) 0.2766(5) 0.0188(7) Uani 1 1 d . . .
N2 N 0.6078(2) 0.9655(11) 0.8490(5) 0.0184(7) Uani 1 1 d . . .
N3 N 0.6946(2) 0.7205(11) 0.5964(5) 0.0190(8) Uani 1 1 d . . .
C1 C 0.5507(3) 0.5968(12) 0.4240(6) 0.0173(9) Uani 1 1 d . . .
C2 C 0.6009(3) 0.7186(12) 0.5767(6) 0.0169(8) Uani 1 1 d . . .
C3 C 0.5515(3) 0.8524(12) 0.7214(6) 0.0167(9) Uani 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 0.0140 0.0070 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0250 0.0140 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2920 0.4290 '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
N1 S1 N1 100.2(3) . 4_655
N3 S2 N2 100.05(19) . .
C1 N1 S1 106.5(3) . .
C3 N2 S2 106.3(3) . .
C2 N3 S2 106.4(3) . .
N1 C1 C1 113.4(2) . 4_655
N1 C1 C2 127.3(4) . .
C1 C1 C2 119.3(2) 4_655 .
N3 C2 C1 125.5(4) . .
N3 C2 C3 113.6(4) . .
C3 C2 C1 120.9(4) . .
N2 C3 C2 113.6(4) . .
N2 C3 C3 126.6(2) . 4_655
C2 C3 C3 119.8(2) . 4_655
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 N1 1.631(4) .
S1 N1 1.631(4) 4_655
S2 N2 1.626(4) .
S2 N3 1.624(4) .
N1 C1 1.337(6) .
N2 C3 1.342(6) .
N3 C2 1.342(5) .
C1 C1 1.442(8) 4_655
C1 C2 1.457(6) .
C2 C3 1.415(6) .
C3 C3 1.463(9) 4_655
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
S1 N1 C1 C1 0.0(3) . 4_655
S1 N1 C1 C2 179.9(4) . .
S2 N2 C3 C2 -1.8(5) . .
S2 N2 C3 C3 177.35(11) . 4_655
S2 N3 C2 C1 178.8(4) . .
S2 N3 C2 C3 -0.8(5) . .
N1 S1 N1 C1 0.0(4) 4_655 .
N1 C1 C2 N3 -2.4(7) . .
N1 C1 C2 C3 177.1(4) . .
N2 S2 N3 C2 -0.3(3) . .
N3 S2 N2 C3 1.2(3) . .
N3 C2 C3 N2 1.8(6) . .
N3 C2 C3 C3 -177.4(3) . 4_655
C1 C1 C2 N3 177.5(3) 4_655 .
C1 C1 C2 C3 -3.0(5) 4_655 .
C1 C2 C3 N2 -177.8(4) . .
C1 C2 C3 C3 3.0(5) . 4_655
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.92(7)
2 0.08(7)
