#------------------------------------------------------------------------------
#$Date: 2022-02-04 21:07:58 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272564 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/53/1565380.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_1565380
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         'C14 H8 Cl4 N2 O S'
_chemical_formula_sum            'C14 H8 Cl4 N2 O S'
_chemical_formula_weight         394.08
_chemical_properties_physical    Moisture-sensitive
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-06-25
_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                95.257(5)
_cell_angle_beta                 106.738(6)
_cell_angle_gamma                101.231(6)
_cell_formula_units_Z            2
_cell_length_a                   7.0073(5)
_cell_length_b                   9.6628(6)
_cell_length_c                   12.0172(7)
_cell_measurement_reflns_used    5355
_cell_measurement_temperature    100.0(5)
_cell_measurement_theta_max      74.9780
_cell_measurement_theta_min      4.5990
_cell_volume                     754.78(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(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    -74.00  32.00   1.00    3.00    --  -42.20  77.00 -60.00  106
  2  ω   -112.00 -16.00   1.00    3.00    --  -42.20 -57.00  60.00   96
  3  ω    -69.00  28.00   1.00    3.00    --  -42.20  57.00-150.00   97
  4  ω      1.00  82.00   1.00    3.00    --   42.20 -99.00   0.00   81
  5  ω     11.00 116.00   1.00    3.00    --   42.20  77.00 150.00  105
  6  ω     31.00 156.00   1.00   11.00    --  111.00 -15.00-150.00  125
  7  ω     36.00 116.00   1.00   11.00    --  111.00-111.00-150.00   80
  8  ω     40.00 135.00   1.00   11.00    --  111.00 -45.00  30.00   95
  9  ω     36.00 116.00   1.00   11.00    --  111.00-111.00  60.00   80
 10  ω     30.00 109.00   1.00   11.00    --  111.00 -94.00-120.00   79
 11  ω     36.00 116.00   1.00   11.00    --  111.00-111.00 150.00   80
 12  ω     31.00 156.00   1.00   11.00    --  111.00 -15.00 -30.00  125
 13  ω     66.00 178.00   1.00   11.00    --  111.00  15.00-150.00  112
 14  ω    100.00 178.00   1.00   11.00    --  111.00 111.00-180.00   78
 15  ω     40.00 135.00   1.00   11.00    --  111.00 -45.00-120.00   95
 16  ω     30.00 109.00   1.00   11.00    --  111.00 -94.00 -90.00   79
 17  ω     41.00 139.00   1.00   11.00    --  111.00 -61.00 120.00   98
 18  ω     36.00 135.00   1.00   11.00    --  111.00 -30.00 120.00   99
 19  ω     36.00 116.00   1.00   11.00    --  111.00-111.00 -30.00   80
 20  ω     57.00 151.00   1.00   11.00    --  111.00 178.00 150.00   94
 21  ω     37.00 142.00   1.00   11.00    --  111.00 -77.00 -90.00  105
 22  ω   -112.00 -16.00   1.00    3.00    --  -42.20 -57.00   0.00   96
 23  ω   -112.00 -16.00   1.00    3.00    --  -42.20 -57.00-150.00   96
 24  ω   -116.00 -11.00   1.00    3.00    --  -42.20 -77.00 -60.00  105
 25  ω   -112.00 -16.00   1.00    3.00    --  -42.20 -57.00 150.00   96
 26  ω     11.00 116.00   1.00    3.00    --   42.20  77.00  60.00  105
 27  ω      1.00  82.00   1.00    3.00    --   42.20 -99.00  90.00   81
 28  ω     66.00 178.00   1.00   11.00    --  111.00  15.00  30.00  112
 29  ω     66.00 178.00   1.00   11.00    --  111.00  15.00 120.00  112
;
_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      0.0826065000
_diffrn_orient_matrix_UB_12      0.0118011000
_diffrn_orient_matrix_UB_13      0.1348244000
_diffrn_orient_matrix_UB_21      -0.1023898000
_diffrn_orient_matrix_UB_22      0.1250611000
_diffrn_orient_matrix_UB_23      0.0139857000
_diffrn_orient_matrix_UB_31      -0.1959457000
_diffrn_orient_matrix_UB_32      -0.1063545000
_diffrn_orient_matrix_UB_33      -0.0015969000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11718
_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         72.122
_diffrn_reflns_theta_min         3.890
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    8.438
_exptl_absorpt_correction_T_max  0.781
_exptl_absorpt_correction_T_min  0.324
_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 red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.734
_exptl_crystal_description       plank
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.222
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.035
_refine_diff_density_max         0.643
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2964
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0387
_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)+(0.0675P)²+0.4578P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1073
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2767
_reflns_number_total             2964
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc04248c2.cif
_cod_data_source_block           abs-391-r1-rf
_cod_depositor_comments
'Adding full bibliography for 1565368--1565385.cif.'
_cod_database_code               1565380
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C14 S1 N2 O1 Cl4 H8'
_chemical_oxdiff_usercomment     ABS-391
_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 100.00
_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.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C3(H3), C7(H7), C4(H4), C6(H6)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_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 1.960
_oxdiff_exptl_absorpt_empirical_full_min 0.668
loop_
_space_group_symop_operation_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_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
Cl4 Cl 0.30010(8) 0.27632(6) 0.94623(5) 0.02623(16) Uani 1 1 d . . . . .
Cl3 Cl 0.23593(9) 0.05969(6) 0.72206(5) 0.02763(16) Uani 1 1 d . . . . .
Cl2 Cl 0.22925(9) 0.17002(6) 0.48421(5) 0.02679(16) Uani 1 1 d . . . . .
S1 S 0.27794(9) 0.70050(6) 0.68588(5) 0.02438(16) Uani 1 1 d . . . . .
Cl1 Cl 0.62249(9) 0.79798(6) 0.78474(5) 0.02974(17) Uani 1 1 d . . . . .
O1 O 0.1947(3) 0.72281(18) 0.01682(15) 0.0285(4) Uani 1 1 d . . . . .
N2 N 0.2575(3) 0.4742(2) 0.49079(17) 0.0214(4) Uani 1 1 d . . . . .
N1 N 0.2356(3) 0.7127(2) 0.55245(18) 0.0252(4) Uani 1 1 d . . . . .
C2 C 0.2372(3) 0.6413(2) 0.3559(2) 0.0212(4) Uani 1 1 d . . . . .
C9 C 0.2629(3) 0.4326(2) 0.5964(2) 0.0209(4) Uani 1 1 d . . . . .
C1 C 0.2490(3) 0.6053(2) 0.4735(2) 0.0214(4) Uani 1 1 d . . . . .
C13 C 0.2876(3) 0.4768(3) 0.8066(2) 0.0231(5) Uani 1 1 d . . . . .
H13 H 0.299722 0.540717 0.872447 0.028 Uiso 1 1 calc R . . . .
C3 C 0.2162(3) 0.5334(2) 0.2637(2) 0.0225(4) Uani 1 1 d . . . . .
H3 H 0.211147 0.440004 0.277968 0.027 Uiso 1 1 calc R . . . .
C11 C 0.2580(3) 0.2381(2) 0.7123(2) 0.0225(5) Uani 1 1 d . . . . .
C7 C 0.2444(3) 0.7812(2) 0.3320(2) 0.0237(5) Uani 1 1 d . . . . .
H7 H 0.257376 0.853888 0.391946 0.028 Uiso 1 1 calc R . . . .
C5 C 0.2109(3) 0.7042(3) 0.1298(2) 0.0237(5) Uani 1 1 d . . . . .
C14 C 0.2770(3) 0.5226(2) 0.6984(2) 0.0211(4) Uani 1 1 d . . . . .
C10 C 0.2510(3) 0.2854(2) 0.6064(2) 0.0217(4) Uani 1 1 d . . . . .
C4 C 0.2029(3) 0.5639(2) 0.1525(2) 0.0235(5) Uani 1 1 d . . . . .
H4 H 0.188634 0.491241 0.092266 0.028 Uiso 1 1 calc R . . . .
C6 C 0.2326(3) 0.8128(2) 0.2203(2) 0.0232(5) Uani 1 1 d . . . . .
H6 H 0.239152 0.906253 0.205879 0.028 Uiso 1 1 calc R . . . .
C12 C 0.2795(3) 0.3349(3) 0.8128(2) 0.0228(5) Uani 1 1 d . . . . .
C8 C 0.2058(5) 0.8649(3) -0.0105(2) 0.0360(6) Uani 1 1 d . . . . .
H8A H 0.198104 0.864090 -0.091642 0.054 Uiso 1 1 calc GR . . . .
H8B H 0.333002 0.926386 0.038550 0.054 Uiso 1 1 calc GR . . . .
H8C H 0.093795 0.899446 0.003260 0.054 Uiso 1 1 calc GR . . . .
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'
O O 0.0492 0.0322 '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
-5 0 3 0.1078
0 -6 0 0.0172
5 -1 -3 0.1048
0 6 0 0.0204
-3 -3 1 0.0805
0 1 -8 0.0145
3 3 -2 0.0841
0 -1 7 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 108.79(8) . . ?
N1 S1 C14 106.78(11) . . ?
C14 S1 Cl1 98.20(8) . . ?
C5 O1 C8 117.72(19) . . ?
C1 N2 C9 121.1(2) . . ?
C1 N1 S1 121.61(17) . . ?
C3 C2 C1 119.7(2) . . ?
C7 C2 C1 121.9(2) . . ?
C7 C2 C3 118.4(2) . . ?
N2 C9 C14 125.4(2) . . ?
N2 C9 C10 118.5(2) . . ?
C14 C9 C10 116.1(2) . . ?
N2 C1 N1 126.7(2) . . ?
N2 C1 C2 118.0(2) . . ?
N1 C1 C2 115.2(2) . . ?
C14 C13 H13 121.0 . . ?
C12 C13 H13 121.0 . . ?
C12 C13 C14 118.0(2) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 120.9(2) . . ?
C4 C3 H3 119.5 . . ?
C10 C11 Cl3 120.14(18) . . ?
C10 C11 C12 120.5(2) . . ?
C12 C11 Cl3 119.32(17) . . ?
C2 C7 H7 119.5 . . ?
C6 C7 C2 120.9(2) . . ?
C6 C7 H7 119.5 . . ?
O1 C5 C4 115.5(2) . . ?
O1 C5 C6 124.7(2) . . ?
C6 C5 C4 119.7(2) . . ?
C9 C14 S1 116.78(17) . . ?
C13 C14 S1 119.30(18) . . ?
C13 C14 C9 123.9(2) . . ?
C9 C10 Cl2 118.14(17) . . ?
C11 C10 Cl2 121.20(18) . . ?
C11 C10 C9 120.7(2) . . ?
C3 C4 C5 120.2(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C7 C6 C5 119.8(2) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C13 C12 Cl4 119.00(19) . . ?
C13 C12 C11 120.8(2) . . ?
C11 C12 Cl4 120.20(18) . . ?
O1 C8 H8A 109.5 . . ?
O1 C8 H8B 109.5 . . ?
O1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
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
Cl4 C12 1.725(2) . ?
Cl3 C11 1.718(2) . ?
Cl2 C10 1.711(2) . ?
S1 Cl1 2.3205(8) . ?
S1 N1 1.564(2) . ?
S1 C14 1.738(2) . ?
O1 C5 1.361(3) . ?
O1 C8 1.434(3) . ?
N2 C9 1.358(3) . ?
N2 C1 1.312(3) . ?
N1 C1 1.377(3) . ?
C2 C1 1.470(3) . ?
C2 C3 1.404(3) . ?
C2 C7 1.402(3) . ?
C9 C14 1.404(3) . ?
C9 C10 1.427(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.399(3) . ?
C13 C12 1.371(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.376(3) . ?
C11 C10 1.382(3) . ?
C11 C12 1.410(3) . ?
C7 H7 0.9300 . ?
C7 C6 1.386(3) . ?
C5 C4 1.401(3) . ?
C5 C6 1.393(3) . ?
C4 H4 0.9300 . ?
C6 H6 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
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
-4.5017 0.4166 2.8350 0.0153 0.5527 0.8333
-0.1430 -6.0787 0.4870 -0.0179 -0.7388 0.6737
4.5273 -0.8028 -2.8261 -0.0165 -0.6035 -0.7972
0.0278 6.1113 -0.4159 0.0183 0.7556 -0.6547
-3.4495 -2.9151 1.0582 -0.1767 0.0034 0.9843
0.1191 1.1419 -7.5219 -0.9908 0.0254 -0.1328
3.4592 3.0318 -1.8420 0.0732 -0.0008 -0.9973
-0.0337 -1.0683 7.4852 0.9938 -0.0255 0.1083
