#------------------------------------------------------------------------------
#$Date: 2022-02-04 21:07:58 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272564 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/53/1565375.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_1565375
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 H9.88 Cl4.12 N2 S'
_chemical_formula_sum            'C15 H9.88 Cl4.12 N2 S'
_chemical_formula_weight         396.33
_chemical_properties_physical    Moisture-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-06-27
_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                 105.795(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8074(3)
_cell_length_b                   15.8724(4)
_cell_length_c                   13.5003(4)
_cell_measurement_reflns_used    12836
_cell_measurement_temperature    100.0(6)
_cell_measurement_theta_max      74.5590
_cell_measurement_theta_min      4.3690
_cell_volume                     1609.82(9)
_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(6)
_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    -65.00  30.00   1.00   10.00    --  -42.45  38.00 -90.00   95
  2  ω   -113.00 -16.00   1.00   10.00    --  -42.45 -57.00 -30.00   97
  3  ω    -74.00  31.00   1.00   10.00    --  -42.45  77.00 -90.00  105
  4  ω    -69.00  28.00   1.00   10.00    --  -42.45  57.00 120.00   97
  5  ω     23.00  97.00   1.00   10.00    --   42.45-125.00-180.00   74
  6  ω     38.00 134.00   1.00   30.00    --  109.57 -45.00 150.00   96
  7  ω     28.00 109.00   1.00   30.00    --  109.57 -94.00  90.00   81
  8  ω     38.00 122.00   1.00   30.00    --  109.57-125.00 -90.00   84
  9  ω     36.00 141.00   1.00   30.00    --  109.57 -77.00 150.00  105
 10  ω     94.00 178.00   1.00   30.00    --  109.57 125.00 150.00   84
 11  ω     86.00 178.00   1.00   30.00    --  109.57  30.00-150.00   92
 12  ω     38.00 122.00   1.00   30.00    --  109.57-125.00  30.00   84
 13  ω     35.00 133.00   1.00   30.00    --  109.57 -30.00-120.00   98
 14  ω     98.00 178.00   1.00   30.00    --  109.57  85.00-140.00   80
 15  ω     94.00 178.00   1.00   30.00    --  109.57 125.00  60.00   84
 16  ω     86.00 178.00   1.00   30.00    --  109.57  30.00 120.00   92
 17  ω     38.00 134.00   1.00   30.00    --  109.57 -45.00  60.00   96
 18  ω   -113.00 -16.00   1.00   10.00    --  -42.45 -57.00-120.00   97
 19  ω   -116.00 -11.00   1.00   10.00    --  -42.45 -77.00-180.00  105
 20  ω   -113.00 -16.00   1.00   10.00    --  -42.45 -57.00  60.00   97
 21  ω   -116.00 -11.00   1.00   10.00    --  -42.45 -77.00  30.00  105
 22  ω      1.00  82.00   1.00   10.00    --   42.45 -99.00  30.00   81
 23  ω     86.00 178.00   1.00   30.00    --  109.57  30.00  60.00   92
 24  ω     64.00 178.00   1.00   30.00    --  109.57  15.00   0.00  114
 25  ω     82.00 178.00   1.00   30.00    --  109.57  61.00   0.00   96
 26  ω     82.00 178.00   1.00   30.00    --  109.57  61.00 150.00   96
 27  ω     86.00 178.00   1.00   30.00    --  109.57  30.00 -90.00   92
;
_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      0.0442674000
_diffrn_orient_matrix_UB_12      -0.0808354000
_diffrn_orient_matrix_UB_13      0.0650528000
_diffrn_orient_matrix_UB_21      -0.1225484000
_diffrn_orient_matrix_UB_22      0.0291048000
_diffrn_orient_matrix_UB_23      0.0656030000
_diffrn_orient_matrix_UB_31      -0.1582905000
_diffrn_orient_matrix_UB_32      -0.0451727000
_diffrn_orient_matrix_UB_33      -0.0743564000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22798
_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         67.907
_diffrn_reflns_theta_min         4.398
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    8.049
_exptl_absorpt_correction_T_max  0.833
_exptl_absorpt_correction_T_min  0.244
_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            'dark yellow'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.635
_exptl_crystal_description       trapezoid
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.315
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.163
_refine_diff_density_min         -0.735
_refine_diff_density_rms         0.117
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.318
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2931
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.318
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0744
_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)+(0.0220P)²+12.6400P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1732
_refine_ls_wR_factor_ref         0.1733
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2898
_reflns_number_total             2931
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc04248c2.cif
_cod_data_source_block           serc211-r1-rf
_cod_depositor_comments
'Adding full bibliography for 1565368--1565385.cif.'
_cod_database_code               1565375
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'S1 N2 Cl4 C15 H10'
_chemical_oxdiff_usercomment
'ABS-284 - Recrystallised (Partial chlorination)'
_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 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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. Others
 Sof(Cl4)=1-FVAR(1)
 Sof(H10)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C14(H14)
3.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C3(H3), C7(H7), C4(H4), C6(H6), C5(H5)
3.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 1.425
_oxdiff_exptl_absorpt_empirical_full_min 0.603
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.84506(18) 0.39968(9) 0.40060(11) 0.0241(3) Uani 1 1 d . . . . .
Cl5 Cl 0.6242(2) 0.60272(10) 0.06882(11) 0.0324(4) Uani 1 1 d . . . . .
Cl2 Cl 0.7721(2) 0.74661(10) 0.49881(13) 0.0365(4) Uani 1 1 d . . . . .
Cl1 Cl 0.6129(2) 0.30808(9) 0.34394(14) 0.0351(4) Uani 1 1 d . . . . .
N2 N 0.7004(6) 0.5379(3) 0.5081(4) 0.0186(10) Uani 1 1 d . . . . .
N1 N 0.8770(6) 0.4125(3) 0.5193(4) 0.0246(11) Uani 1 1 d . . . . .
C1 C 0.7875(7) 0.4735(4) 0.5589(5) 0.0207(12) Uani 1 1 d . . . . .
C8 C 0.6892(7) 0.5495(3) 0.4064(4) 0.0195(11) Uani 1 1 d . . . . .
C12 C 0.7229(7) 0.5033(4) 0.2365(5) 0.0233(12) Uani 1 1 d . . . . .
C13 C 0.7420(7) 0.4902(4) 0.3422(4) 0.0210(12) Uani 1 1 d . . . . .
C2 C 0.8013(7) 0.4665(4) 0.6703(5) 0.0232(12) Uani 1 1 d . . . . .
C11 C 0.6515(7) 0.5802(4) 0.1973(5) 0.0242(12) Uani 1 1 d . . . . .
C10 C 0.6015(7) 0.6414(4) 0.2585(5) 0.0240(13) Uani 1 1 d . . . . .
H10 H 0.556113 0.692489 0.229190 0.029 Uiso 0.877(7) 1 calc R . P A 1
C9 C 0.6179(7) 0.6276(4) 0.3606(5) 0.0219(12) Uani 1 1 d . . . . .
C3 C 0.7318(8) 0.5308(4) 0.7186(5) 0.0272(13) Uani 1 1 d . . . . .
H3 H 0.680264 0.577994 0.681375 0.033 Uiso 1 1 calc R . . . .
C7 C 0.8829(7) 0.3968(4) 0.7269(5) 0.0251(13) Uani 1 1 d . . . . .
H7 H 0.930821 0.354234 0.695273 0.030 Uiso 1 1 calc R . . . .
C4 C 0.7401(8) 0.5241(4) 0.8213(5) 0.0291(14) Uani 1 1 d . . . . .
H4 H 0.691645 0.566371 0.853042 0.035 Uiso 1 1 calc R . . . .
C6 C 0.8919(8) 0.3917(4) 0.8305(5) 0.0312(14) Uani 1 1 d . . . . .
H6 H 0.946633 0.345434 0.868545 0.037 Uiso 1 1 calc R . . . .
C5 C 0.8203(8) 0.4545(4) 0.8784(5) 0.0314(14) Uani 1 1 d . . . . .
H5 H 0.825752 0.450341 0.947924 0.038 Uiso 1 1 calc R . . . .
C15 C 0.7767(8) 0.4371(4) 0.1710(5) 0.0287(13) Uani 1 1 d . . . . .
H15A H 0.872577 0.458034 0.145992 0.043 Uiso 1 1 calc GR . . . .
H15B H 0.677015 0.423601 0.113721 0.043 Uiso 1 1 calc GR . . . .
H15C H 0.814996 0.387320 0.211395 0.043 Uiso 1 1 calc GR . . . .
C14 C 0.5729(8) 0.6918(4) 0.4315(5) 0.0291(14) Uani 1 1 d . . . . .
H14 H 0.523094 0.662982 0.481590 0.035 Uiso 1 1 calc R . . . .
Cl3 Cl 0.4179(2) 0.76932(11) 0.36451(16) 0.0441(5) Uani 1 1 d . . . . .
Cl4 Cl 0.5106(15) 0.7300(7) 0.2167(9) 0.025(4) Uani 0.123(7) 1 d . . P A -1
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 4 8 0.0345
5 3 -2 0.1193
0 -4 -8 0.0179
-3 0 -5 0.0957
0 -10 1 0.0145
3 0 5 0.1027
0 10 -1 0.0101
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 108.4(2) . . ?
N1 S1 C13 106.5(3) . . ?
C13 S1 Cl1 98.51(19) . . ?
C1 N2 C8 120.8(5) . . ?
C1 N1 S1 122.0(4) . . ?
N2 C1 N1 126.0(5) . . ?
N2 C1 C2 118.2(5) . . ?
N1 C1 C2 115.7(5) . . ?
N2 C8 C13 125.3(5) . . ?
N2 C8 C9 117.6(5) . . ?
C13 C8 C9 117.1(5) . . ?
C13 C12 C15 121.5(5) . . ?
C11 C12 C13 115.9(5) . . ?
C11 C12 C15 122.6(6) . . ?
C8 C13 S1 116.8(4) . . ?
C12 C13 S1 119.5(4) . . ?
C12 C13 C8 123.7(5) . . ?
C3 C2 C1 119.2(5) . . ?
C7 C2 C1 120.7(5) . . ?
C7 C2 C3 120.1(6) . . ?
C12 C11 Cl5 119.5(5) . . ?
C12 C11 C10 122.3(6) . . ?
C10 C11 Cl5 118.2(5) . . ?
C11 C10 H10 119.3 . . ?
C11 C10 Cl4 124.6(6) . . ?
C9 C10 C11 121.4(5) . . ?
C9 C10 H10 119.3 . . ?
C9 C10 Cl4 113.9(6) . . ?
Cl4 C10 H10 6.2 . . ?
C8 C9 C14 116.3(5) . . ?
C10 C9 C8 119.6(5) . . ?
C10 C9 C14 124.0(5) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.7(6) . . ?
C4 C3 H3 120.1 . . ?
C2 C7 H7 120.3 . . ?
C6 C7 C2 119.3(6) . . ?
C6 C7 H7 120.3 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.7(6) . . ?
C5 C4 H4 119.7 . . ?
C7 C6 H6 119.6 . . ?
C7 C6 C5 120.9(6) . . ?
C5 C6 H6 119.6 . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.3(6) . . ?
C6 C5 H5 120.3 . . ?
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 . . ?
Cl2 C14 H14 109.2 . . ?
C9 C14 Cl2 109.3(4) . . ?
C9 C14 H14 109.2 . . ?
C9 C14 Cl3 112.8(5) . . ?
Cl3 C14 Cl2 107.2(3) . . ?
Cl3 C14 H14 109.2 . . ?
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 2.287(2) . ?
S1 N1 1.567(5) . ?
S1 C13 1.729(6) . ?
Cl5 C11 1.726(6) . ?
Cl2 C14 1.798(7) . ?
N2 C1 1.313(7) . ?
N2 C8 1.365(7) . ?
N1 C1 1.383(7) . ?
C1 C2 1.483(8) . ?
C8 C13 1.415(8) . ?
C8 C9 1.428(8) . ?
C12 C13 1.408(8) . ?
C12 C11 1.386(8) . ?
C12 C15 1.505(8) . ?
C2 C3 1.398(8) . ?
C2 C7 1.396(8) . ?
C11 C10 1.398(9) . ?
C10 H10 0.9300 . ?
C10 C9 1.366(9) . ?
C10 Cl4 1.608(12) . ?
C9 C14 1.504(8) . ?
C3 H3 0.9300 . ?
C3 C4 1.375(9) . ?
C7 H7 0.9300 . ?
C7 C6 1.384(9) . ?
C4 H4 0.9300 . ?
C4 C5 1.393(9) . ?
C6 H6 0.9300 . ?
C6 C5 1.387(9) . ?
C5 H5 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C14 H14 0.9800 . ?
C14 Cl3 1.790(6) . ?
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
-0.0028 4.2972 7.6619 0.1509 0.6281 -0.7634
4.8900 2.7008 -2.4762 -0.1629 -0.6831 -0.7119
0.0157 -4.2911 -7.6702 -0.1514 -0.6300 0.7617
-3.3915 0.0647 -4.6721 -0.4593 0.1110 0.8813
-0.4487 -10.2499 0.6204 0.8490 -0.2026 0.4879
3.3769 -0.4008 4.6927 0.4872 -0.1176 -0.8654
0.2603 10.2477 -0.8792 -0.8740 0.2087 -0.4387
