#------------------------------------------------------------------------------
#$Date: 2022-02-04 21:07:58 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272564 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/53/1565381.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_1565381
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         'Cl, C14 H10 Cl4 N3 S, Cl H'
_chemical_formula_sum            'C14 H11 Cl6 N3 S'
_chemical_formula_weight         466.02
_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   mixed
_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                90.608(3)
_cell_angle_beta                 101.838(3)
_cell_angle_gamma                105.699(2)
_cell_formula_units_Z            2
_cell_length_a                   8.1354(2)
_cell_length_b                   9.2414(2)
_cell_length_c                   12.9459(6)
_cell_measurement_reflns_used    11291
_cell_measurement_temperature    100.0(5)
_cell_measurement_theta_max      75.5540
_cell_measurement_theta_min      4.9550
_cell_volume                     914.81(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    -66.00  32.00   1.00    1.50    --  -41.91  38.00-150.00   98
  2  ω   -116.00 -17.00   1.00    1.50    --  -41.91 -38.00  30.00   99
  3  ω    -96.00  -2.00   1.00    1.50    --  -41.91 125.00 -60.00   94
  4  ω    -32.00  66.00   1.00    1.50    --   41.91 -38.00-120.00   98
  5  ω     23.00  98.00   1.00    1.50    --   41.91-125.00 -90.00   75
  6  ω     37.00 117.00   1.00    3.00    --  112.00-115.00 -46.00   80
  7  ω     84.00 178.00   1.00    3.00    --  112.00  30.00-120.00   94
  8  ω     36.00 145.00   1.00    3.00    --  112.00 -77.00 -90.00  109
  9  ω     29.00 109.00   1.00    3.00    --  112.00 -94.00-150.00   80
 10  ω     36.00 140.00   1.00    3.00    --  112.00 -30.00 -90.00  104
 11  ω     57.00 151.00   1.00    3.00    --  112.00 178.00 -90.00   94
 12  ω     36.00 116.00   1.00    3.00    --  112.00-111.00   0.00   80
 13  ω     29.00 109.00   1.00    3.00    --  112.00 -94.00  60.00   80
 14  ω     29.00 109.00   1.00    3.00    --  112.00 -94.00 120.00   80
 15  ω    100.00 178.00   1.00    3.00    --  112.00 111.00   0.00   78
 16  ω     36.00 116.00   1.00    3.00    --  112.00-111.00  90.00   80
 17  ω     79.00 178.00   1.00    3.00    --  112.00  77.00   0.00   99
 18  ω    100.00 178.00   1.00    3.00    --  112.00 111.00  60.00   78
 19  ω     29.00 109.00   1.00    3.00    --  112.00 -94.00 -90.00   80
 20  ω     86.00 178.00   1.00    3.00    --  112.00  45.00 150.00   92
 21  ω     39.00 138.00   1.00    3.00    --  112.00 -45.00  60.00   99
 22  ω    100.00 178.00   1.00    3.00    --  112.00 111.00-150.00   78
 23  ω     59.00 178.00   1.00    3.00    --  112.00  15.00 -30.00  119
 24  ω   -118.00  -9.00   1.00    1.50    --  -41.91 -77.00-150.00  109
 25  ω   -118.00  -9.00   1.00    1.50    --  -41.91 -77.00  30.00  109
 26  ω   -118.00  -9.00   1.00    1.50    --  -41.91 -77.00 -60.00  109
 27  ω     64.00 124.00   1.00    1.50    --   41.91 170.00-173.00   60
 28  ω      9.00 118.00   1.00    1.50    --   41.91  77.00-150.00  109
 29  ω     14.00 114.00   1.00    1.50    --   41.91  57.00 150.00  100
 30  ω     84.00 178.00   1.00    3.00    --  112.00  30.00  90.00   94
 31  ω     83.00 178.00   1.00    3.00    --  112.00  61.00-120.00   95
 32  ω     79.00 178.00   1.00    3.00    --  112.00  77.00 -90.00   99
 33  ω     79.00 178.00   1.00    3.00    --  112.00  77.00  30.00   99
 34  ω     83.00 178.00   1.00    3.00    --  112.00  61.00 -30.00   95
 35  ω     79.00 178.00   1.00    3.00    --  112.00  77.00  90.00   99
 36  ω     79.00 130.00   1.00    3.00    --  112.00  77.00  60.00   51
 37  ω     83.00 178.00   1.00    3.00    --  112.00  61.00-180.00   95
;
_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      -0.0742465000
_diffrn_orient_matrix_UB_12      -0.0127934000
_diffrn_orient_matrix_UB_13      -0.1202340000
_diffrn_orient_matrix_UB_21      -0.0584930000
_diffrn_orient_matrix_UB_22      -0.1729592000
_diffrn_orient_matrix_UB_23      0.0011653000
_diffrn_orient_matrix_UB_31      -0.1779123000
_diffrn_orient_matrix_UB_32      0.0074203000
_diffrn_orient_matrix_UB_33      0.0199692000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17679
_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         69.505
_diffrn_reflns_theta_min         3.497
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    9.662
_exptl_absorpt_correction_T_max  0.694
_exptl_absorpt_correction_T_min  0.174
_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 yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.692
_exptl_crystal_description       plank
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.393
_exptl_crystal_size_mid          0.097
_exptl_crystal_size_min          0.043
_refine_diff_density_max         1.328
_refine_diff_density_min         -0.975
_refine_diff_density_rms         0.219
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.209
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3432
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.209
_refine_ls_R_factor_all          0.1028
_refine_ls_R_factor_gt           0.1019
_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)+36.6427P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2915
_refine_ls_wR_factor_ref         0.2917
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3306
_reflns_number_total             3432
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc04248c2.cif
_cod_data_source_block           abs-819-twin-r1_twin1_hklf4-rf
_cod_depositor_comments
'Adding full bibliography for 1565368--1565385.cif.'
_cod_database_code               1565381
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'N3 S1 Cl6 C14 H111'
_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, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C11(H11), C5(H5), C6(H6), C3(H3A), C4(H4)
;
_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 1.432
_oxdiff_exptl_absorpt_empirical_full_min 0.613
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
Cl6 Cl 0.1488(3) 0.7459(3) 0.5225(2) 0.0251(6) Uani 1 1 d . . . . .
Cl1 Cl -0.0216(4) 0.3022(3) 0.0796(2) 0.0267(6) Uani 1 1 d . . . . .
S1 S -0.0408(3) 0.3704(3) 0.2421(2) 0.0184(6) Uani 1 1 d . . . . .
Cl3 Cl -0.3581(4) 0.8927(4) -0.0298(2) 0.0317(7) Uani 1 1 d . . . . .
Cl4 Cl -0.5939(3) 0.5756(4) 0.0942(2) 0.0265(7) Uani 1 1 d . . . . .
Cl2 Cl 0.0295(5) 1.0443(3) 0.3121(3) 0.0362(8) Uani 1 1 d . . . . .
Cl5 Cl 0.5066(5) 1.1504(4) 0.2940(3) 0.0443(9) Uani 1 1 d . . . . .
N2 N 0.1645(11) 0.6981(10) 0.2602(7) 0.0166(18) Uani 1 1 d . . . . .
N1 N 0.1483(12) 0.4438(10) 0.3080(7) 0.0187(19) Uani 1 1 d . . . . .
N3 N 0.7654(12) 0.7258(11) 0.4506(8) 0.024(2) Uani 1 1 d . . . . .
H3 H 0.874943 0.753704 0.479838 0.028 Uiso 1 1 calc R . . . .
C12 C -0.1260(13) 0.5204(12) 0.2072(8) 0.016(2) Uani 1 1 d . . . . .
C9 C -0.2623(14) 0.7601(13) 0.1475(8) 0.019(2) Uani 1 1 d . . . . .
C11 C -0.3043(14) 0.4926(13) 0.1686(9) 0.019(2) Uani 1 1 d . . . . .
H11 H -0.377987 0.394941 0.161385 0.023 Uiso 1 1 calc R . . . .
C2 C 0.4190(13) 0.6391(12) 0.3555(9) 0.018(2) Uani 1 1 d . . . . .
C1 C 0.2302(14) 0.5935(12) 0.3019(8) 0.018(2) Uani 1 1 d . . . . .
C7 C -0.0096(14) 0.6676(12) 0.2187(8) 0.018(2) Uani 1 1 d . . . . .
C8 C -0.0800(14) 0.7864(12) 0.1858(9) 0.019(2) Uani 1 1 d . . . . .
C5 C 0.6888(14) 0.5811(13) 0.4239(9) 0.021(2) Uani 1 1 d . . . . .
H5 H 0.752596 0.511091 0.437029 0.025 Uiso 1 1 calc R . . . .
C6 C 0.5136(14) 0.5349(12) 0.3765(8) 0.018(2) Uani 1 1 d . . . . .
H6 H 0.458602 0.433061 0.358480 0.022 Uiso 1 1 calc R . . . .
C3 C 0.5029(15) 0.7911(13) 0.3855(9) 0.023(2) Uani 1 1 d . . . . .
H3A H 0.441639 0.863080 0.373191 0.028 Uiso 1 1 calc R . . . .
C4 C 0.6774(15) 0.8324(13) 0.4336(10) 0.025(2) Uani 1 1 d . . . . .
H4 H 0.735316 0.933004 0.454555 0.030 Uiso 1 1 calc R . . . .
C10 C -0.3697(15) 0.6121(14) 0.1412(9) 0.022(2) Uani 1 1 d . . . . .
C14 C -0.3391(16) 0.8866(14) 0.1104(9) 0.024(2) Uani 1 1 d . . . . .
H14A H -0.264146 0.981604 0.145870 0.029 Uiso 1 1 calc R . . . .
H14B H -0.453311 0.870005 0.127137 0.029 Uiso 1 1 calc R . . . .
C13 C 0.0395(15) 0.9422(13) 0.1946(10) 0.024(2) Uani 1 1 d . . . . .
H13A H 0.005368 0.993987 0.132570 0.029 Uiso 1 1 calc R . . . .
H13B H 0.158346 0.937763 0.198408 0.029 Uiso 1 1 calc R . . . .
H5A H 0.741(16) 1.233(13) 0.323(9) 0.02(3) 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 0.0181 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 0 0.0442
0 -6 0 0.0497
-5 2 2 0.2019
0 0 8 0.0193
5 -2 -2 0.1830
0 0 -8 0.0211
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 108.2(4) . . ?
N1 S1 C12 105.1(5) . . ?
C12 S1 Cl1 96.9(4) . . ?
C1 N2 C7 120.4(9) . . ?
C1 N1 S1 120.6(8) . . ?
C5 N3 H3 118.7 . . ?
C5 N3 C4 122.5(10) . . ?
C4 N3 H3 118.7 . . ?
C11 C12 S1 119.2(8) . . ?
C11 C12 C7 122.3(10) . . ?
C7 C12 S1 118.5(8) . . ?
C8 C9 C14 121.2(10) . . ?
C10 C9 C8 118.3(10) . . ?
C10 C9 C14 120.5(10) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 C12 118.5(10) . . ?
C10 C11 H11 120.7 . . ?
C6 C2 C1 121.8(10) . . ?
C6 C2 C3 119.0(10) . . ?
C3 C2 C1 119.2(10) . . ?
N2 C1 N1 129.1(10) . . ?
N2 C1 C2 117.3(10) . . ?
N1 C1 C2 113.6(9) . . ?
N2 C7 C12 123.3(10) . . ?
N2 C7 C8 119.1(10) . . ?
C8 C7 C12 117.6(10) . . ?
C9 C8 C13 120.3(10) . . ?
C7 C8 C9 120.7(10) . . ?
C7 C8 C13 119.0(10) . . ?
N3 C5 H5 120.3 . . ?
N3 C5 C6 119.4(10) . . ?
C6 C5 H5 120.3 . . ?
C2 C6 H6 119.8 . . ?
C5 C6 C2 120.4(10) . . ?
C5 C6 H6 119.8 . . ?
C2 C3 H3A 120.6 . . ?
C4 C3 C2 118.8(11) . . ?
C4 C3 H3A 120.6 . . ?
N3 C4 C3 119.9(11) . . ?
N3 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C9 C10 Cl4 119.6(9) . . ?
C11 C10 Cl4 118.0(9) . . ?
C11 C10 C9 122.4(10) . . ?
Cl3 C14 H14A 109.9 . . ?
Cl3 C14 H14B 109.9 . . ?
C9 C14 Cl3 108.8(8) . . ?
C9 C14 H14A 109.9 . . ?
C9 C14 H14B 109.9 . . ?
H14A C14 H14B 108.3 . . ?
Cl2 C13 H13A 109.7 . . ?
Cl2 C13 H13B 109.7 . . ?
C8 C13 Cl2 109.8(8) . . ?
C8 C13 H13A 109.7 . . ?
C8 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
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
Cl1 S1 2.238(4) . ?
S1 N1 1.562(9) . ?
S1 C12 1.735(11) . ?
Cl3 C14 1.793(12) . ?
Cl4 C10 1.738(11) . ?
Cl2 C13 1.808(13) . ?
Cl5 H5A 1.81(12) . ?
N2 C1 1.298(14) . ?
N2 C7 1.357(14) . ?
N1 C1 1.374(14) . ?
N3 H3 0.8600 . ?
N3 C5 1.322(15) . ?
N3 C4 1.361(15) . ?
C12 C11 1.384(15) . ?
C12 C7 1.418(15) . ?
C9 C8 1.416(15) . ?
C9 C10 1.401(17) . ?
C9 C14 1.507(15) . ?
C11 H11 0.9300 . ?
C11 C10 1.370(16) . ?
C2 C1 1.492(15) . ?
C2 C6 1.383(15) . ?
C2 C3 1.397(16) . ?
C7 C8 1.402(15) . ?
C8 C13 1.491(16) . ?
C5 H5 0.9300 . ?
C5 C6 1.377(15) . ?
C6 H6 0.9300 . ?
C3 H3A 0.9300 . ?
C3 C4 1.374(16) . ?
C4 H4 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 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
0.0164 5.7686 -0.4123 -0.0254 -0.9992 0.0317
0.0550 -5.7900 0.3708 0.0254 0.9986 -0.0453
-5.2571 1.8117 2.4210 0.0761 -0.0030 0.9971
-0.0810 -0.0610 8.2375 -0.9836 0.0249 0.1784
5.2775 -1.8261 -1.7437 -0.1588 0.0051 -0.9873
-0.0036 0.0903 -8.2111 0.9864 -0.0250 -0.1627
