#------------------------------------------------------------------------------
#$Date: 2022-02-04 21:07:58 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272564 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/53/1565376.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_1565376
loop_
_publ_author_name
'Borys, Andryj M.'
'Clark, Ewan R.'
'Saines, Paul J.'
'Alberola, Antonio'
'Rawson, Jeremy M.'
_publ_section_title
;
 A short, versatile route towards benzothiadiazinyl radicals.
;
_journal_issue                   1
_journal_name_full               'Chemical science'
_journal_page_first              149
_journal_page_last               158
_journal_paper_doi               10.1039/d1sc04248c
_journal_volume                  13
_journal_year                    2021
_chemical_formula_moiety         'C15 H10 Cl4 N2 S'
_chemical_formula_sum            'C15 H10 Cl4 N2 S'
_chemical_formula_weight         392.11
_chemical_properties_physical    Moisture-sensitive
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-06-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-08-03 deposited with the CCDC.	2021-11-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.598(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.38990(10)
_cell_length_b                   10.5325(2)
_cell_length_c                   20.5855(4)
_cell_measurement_reflns_used    10953
_cell_measurement_temperature    100.0(5)
_cell_measurement_theta_max      75.2570
_cell_measurement_theta_min      4.7080
_cell_volume                     1591.64(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2887
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -113.00 -16.00   1.00    3.00    --  -42.70 -57.00  90.00   97
  2  ω    -69.00  27.00   1.00    3.00    --  -42.70  57.00-120.00   96
  3  ω    -65.00  30.00   1.00    3.00    --  -42.70  38.00  30.00   95
  4  ω      1.00  83.00   1.00    3.00    --   42.70 -99.00  30.00   82
  5  ω      1.00  83.00   1.00    3.00    --   42.70 -99.00 -60.00   82
  6  ω     31.00 156.00   1.00   12.50    --  111.00 -15.00   0.00  125
  7  ω     36.00 116.00   1.00   12.50    --  111.00-111.00-150.00   80
  8  ω     87.00 178.00   1.00   12.50    --  111.00  45.00  90.00   91
  9  ω     66.00 178.00   1.00   12.50    --  111.00  15.00-120.00  112
 10  ω    100.00 178.00   1.00   12.50    --  111.00 111.00 -90.00   78
 11  ω     87.00 178.00   1.00   12.50    --  111.00  45.00-180.00   91
 12  ω    100.00 178.00   1.00   12.50    --  111.00 111.00-150.00   78
 13  ω     36.00 116.00   1.00   12.50    --  111.00-111.00 -90.00   80
 14  ω     30.00 109.00   1.00   12.50    --  111.00 -94.00 -30.00   79
 15  ω     37.00 116.00   1.00   12.50    --  111.00-111.00  60.00   79
 16  ω     71.00 116.00   1.00   12.50    --  111.00-111.00 -30.00   45
 17  ω     52.00  83.00   1.00   12.50    --  111.00 -45.00 150.00   31
 18  ω     90.00 116.00   1.00   12.50    --  111.00-111.00 150.00   26
 19  ω    116.00 176.00   1.00   12.50    --  111.00 111.00  30.00   60
 20  ω     42.00  86.00   1.00   12.50    --  111.00 -45.00   0.00   44
 21  ω     94.00 135.00   1.00   12.50    --  111.00 -45.00   0.00   41
 22  ω     60.00  87.00   1.00   12.50    --  111.00 -94.00-150.00   27
 23  ω     31.00  69.00   1.00   12.50    --  111.00 -94.00 -60.00   38
 24  ω     31.00  60.00   1.00   12.50    --  111.00 -94.00  30.00   29
 25  ω     98.00 125.00   1.00   12.50    --  111.00  45.00 120.00   27
 26  ω    148.00 175.00   1.00   12.50    --  111.00  45.00 120.00   27
 27  ω     69.00 108.00   1.00   12.50    --  111.00 -77.00  30.00   39
 28  ω     69.00 107.00   1.00   12.50    --  111.00 -94.00 120.00   38
 29  ω     58.00 114.00   1.00   12.50    --  111.00-111.00  30.00   56
 30  ω     88.00 178.00   1.00   12.50    --  111.00  45.00   0.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0334482000
_diffrn_orient_matrix_UB_12      -0.0326049000
_diffrn_orient_matrix_UB_13      0.0733706000
_diffrn_orient_matrix_UB_21      0.0141451000
_diffrn_orient_matrix_UB_22      0.1425241000
_diffrn_orient_matrix_UB_23      0.0166349000
_diffrn_orient_matrix_UB_31      -0.2066450000
_diffrn_orient_matrix_UB_32      0.0045270000
_diffrn_orient_matrix_UB_33      0.0042072000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            19045
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.489
_diffrn_reflns_theta_min         4.324
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    7.949
_exptl_absorpt_correction_T_max  0.793
_exptl_absorpt_correction_T_min  0.317
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light orange'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_description       needle
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.377
_exptl_crystal_size_mid          0.042
_exptl_crystal_size_min          0.038
_refine_diff_density_max         1.262
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3201
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0456
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0552P)²+3.3699P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1183
_refine_ls_wR_factor_ref         0.1198
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3031
_reflns_number_total             3201
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc04248c2.cif
_cod_data_source_block           serc256-r1-rf
_cod_depositor_comments
'Adding full bibliography for 1565368--1565385.cif.'
_cod_database_code               1565376
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'S1 N2 Cl4 C15 H10'
_chemical_oxdiff_usercomment     ABS-551
_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 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C3(H3), C6(H6), C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.363
_oxdiff_exptl_absorpt_empirical_full_min 0.597
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
S1 S 0.14967(9) 0.75980(6) 0.52057(3) 0.02383(17) Uani 1 1 d . . . . .
Cl1 Cl 0.41138(10) 0.84450(7) 0.57457(3) 0.03172(19) Uani 1 1 d . . . . .
Cl4 Cl 0.26055(11) 0.94928(8) 0.28505(4) 0.0362(2) Uani 1 1 d . . . . .
Cl3 Cl 0.34887(11) 0.67988(8) 0.23875(3) 0.0356(2) Uani 1 1 d . . . . .
Cl2 Cl 0.17832(11) 0.37081(8) 0.31840(4) 0.0425(2) Uani 1 1 d . . . . .
N2 N 0.2841(3) 0.5170(2) 0.46684(11) 0.0221(5) Uani 1 1 d . . . . .
N1 N 0.1363(3) 0.6227(2) 0.54952(12) 0.0255(5) Uani 1 1 d . . . . .
C2 C 0.2318(3) 0.4061(3) 0.56451(13) 0.0223(5) Uani 1 1 d . . . . .
C8 C 0.2710(3) 0.6203(3) 0.42611(13) 0.0213(5) Uani 1 1 d . . . . .
C12 C 0.2119(3) 0.8475(3) 0.40080(13) 0.0219(5) Uani 1 1 d . . . . .
C1 C 0.2211(3) 0.5223(3) 0.52323(13) 0.0214(5) Uani 1 1 d . . . . .
C7 C 0.1821(4) 0.4103(3) 0.62745(14) 0.0234(5) Uani 1 1 d . . . . .
H7 H 0.140698 0.485927 0.643741 0.028 Uiso 1 1 calc R . . . .
C13 C 0.2167(3) 0.7429(3) 0.44355(13) 0.0206(5) Uani 1 1 d . . . . .
C15 C 0.1576(4) 0.9806(3) 0.42083(15) 0.0274(6) Uani 1 1 d . . . . .
H15A H 0.056847 1.010100 0.391086 0.041 Uiso 1 1 calc GR . . . .
H15B H 0.259029 1.037189 0.419650 0.041 Uiso 1 1 calc GR . . . .
H15C H 0.122976 0.978086 0.464348 0.041 Uiso 1 1 calc GR . . . .
C3 C 0.2917(4) 0.2921(3) 0.53984(14) 0.0253(6) Uani 1 1 d . . . . .
H3 H 0.323457 0.288647 0.497454 0.030 Uiso 1 1 calc R . . . .
C6 C 0.1938(4) 0.3023(3) 0.66614(14) 0.0266(6) Uani 1 1 d . . . . .
H6 H 0.160442 0.305721 0.708313 0.032 Uiso 1 1 calc R . . . .
C11 C 0.2583(4) 0.8237(3) 0.33880(14) 0.0248(6) Uani 1 1 d . . . . .
C9 C 0.3163(4) 0.5997(3) 0.36166(14) 0.0237(5) Uani 1 1 d . . . . .
C10 C 0.3056(4) 0.7007(3) 0.31903(13) 0.0250(6) Uani 1 1 d . . . . .
C4 C 0.3038(4) 0.1841(3) 0.57836(16) 0.0278(6) Uani 1 1 d . . . . .
H4 H 0.344198 0.108292 0.561887 0.033 Uiso 1 1 calc R . . . .
C5 C 0.2554(4) 0.1887(3) 0.64194(15) 0.0288(6) Uani 1 1 d . . . . .
H5 H 0.264301 0.116293 0.667968 0.035 Uiso 1 1 calc R . . . .
C14 C 0.3746(4) 0.4687(3) 0.34361(16) 0.0296(6) Uani 1 1 d . . . . .
H14A H 0.446031 0.430027 0.380909 0.035 Uiso 1 1 calc R . . . .
H14B H 0.450436 0.474389 0.308276 0.035 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 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 6 7 0.0163
5 0 -2 0.1913
0 -6 -7 0.0190
-5 0 2 0.1786
0 -4 11 0.0136
0 4 -11 0.0181
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
_geom_angle_publ_flag
N1 S1 Cl1 105.06(10) . . ?
N1 S1 C13 106.95(13) . . ?
C13 S1 Cl1 99.80(9) . . ?
C1 N2 C8 120.4(2) . . ?
C1 N1 S1 120.5(2) . . ?
C7 C2 C1 120.3(3) . . ?
C7 C2 C3 119.7(3) . . ?
C3 C2 C1 119.9(2) . . ?
N2 C8 C13 125.0(2) . . ?
N2 C8 C9 116.2(2) . . ?
C13 C8 C9 118.8(3) . . ?
C13 C12 C15 122.5(2) . . ?
C11 C12 C13 116.4(3) . . ?
C11 C12 C15 121.1(3) . . ?
N2 C1 N1 127.7(3) . . ?
N2 C1 C2 118.3(2) . . ?
N1 C1 C2 113.9(2) . . ?
C2 C7 H7 119.8 . . ?
C6 C7 C2 120.3(3) . . ?
C6 C7 H7 119.8 . . ?
C8 C13 S1 116.7(2) . . ?
C12 C13 S1 120.3(2) . . ?
C12 C13 C8 123.0(2) . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3 120.0 . . ?
C7 C6 H6 120.0 . . ?
C7 C6 C5 120.1(3) . . ?
C5 C6 H6 120.0 . . ?
C12 C11 Cl4 118.3(2) . . ?
C12 C11 C10 121.9(3) . . ?
C10 C11 Cl4 119.8(2) . . ?
C8 C9 C14 118.4(3) . . ?
C10 C9 C8 118.3(3) . . ?
C10 C9 C14 123.3(3) . . ?
C11 C10 Cl3 118.0(2) . . ?
C9 C10 Cl3 120.4(2) . . ?
C9 C10 C11 121.5(3) . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.1(3) . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 119.6(3) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
Cl2 C14 H14A 109.5 . . ?
Cl2 C14 H14B 109.5 . . ?
C9 C14 Cl2 110.57(19) . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 Cl1 2.2974(10) . ?
S1 N1 1.570(2) . ?
S1 C13 1.724(3) . ?
Cl4 C11 1.726(3) . ?
Cl3 C10 1.733(3) . ?
Cl2 C14 1.806(3) . ?
N2 C8 1.370(4) . ?
N2 C1 1.300(4) . ?
N1 C1 1.372(3) . ?
C2 C1 1.487(4) . ?
C2 C7 1.387(4) . ?
C2 C3 1.396(4) . ?
C8 C13 1.411(4) . ?
C8 C9 1.422(4) . ?
C12 C13 1.408(4) . ?
C12 C15 1.527(4) . ?
C12 C11 1.382(4) . ?
C7 H7 0.9300 . ?
C7 C6 1.385(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C3 H3 0.9300 . ?
C3 C4 1.383(4) . ?
C6 H6 0.9300 . ?
C6 C5 1.393(4) . ?
C11 C10 1.414(4) . ?
C9 C10 1.376(4) . ?
C9 C14 1.505(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.397(4) . ?
C5 H5 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0470 5.7773 7.0815 0.3328 0.9419 0.0462
4.7927 -0.1024 -2.1338 0.0071 0.0177 -0.9998
0.1422 -5.7707 -7.1525 -0.3319 -0.9394 -0.0856
-4.7864 0.1820 2.3897 0.0093 -0.0020 1.0000
-0.1265 -3.6364 11.2718 0.9414 -0.3326 0.0571
0.2849 3.6203 -11.3200 -0.9391 0.3317 -0.0901
