A short, versatile route towards benzothiadiazinyl radicals.
Borys, Andryj M.; Clark, Ewan R.; Saines, Paul J.; Alberola, Antonio; Rawson, Jeremy M.; Chemical science 13 (2021) 149–158; doi:10.1039/d1sc04248c

data_1565383
_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         'C13 H6 Cl3 N2 S, C0.5 H Cl'
_chemical_formula_sum            'C13.5 H7 Cl4 N2 S'
_chemical_formula_weight         371.07
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-06-28
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.7712(3)
_cell_length_b                   13.1359(2)
_cell_length_c                   13.0495(2)
_cell_measurement_reflns_used    52319
_cell_measurement_temperature    100.0(7)
_cell_measurement_theta_max      76.1040
_cell_measurement_theta_min      4.7660
_cell_volume                     2874.87(8)
_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(7)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2774
_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  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -116.00 -17.00   1.00    5.00    --  -41.95 -38.00-180.00   99
  2  \w   -116.00 -17.00   1.00    5.00    --  -41.95 -38.00 -90.00   99
  3  \w    -32.00  66.00   1.00    5.00    --   41.95 -38.00  30.00   98
  4  \w      1.00  83.00   1.00    5.00    --   41.95 -99.00 150.00   82
  5  \w     23.00  98.00   1.00    5.00    --   41.95-125.00   0.00   75
  6  \w      1.00  83.00   1.00    5.00    --   41.95 -99.00   0.00   82
  7  \w     23.00  98.00   1.00    5.00    --   41.95-125.00  90.00   75
  8  \w     35.00 138.00   1.00   17.50    --  111.00 -31.00  -3.76  103
  9  \w     83.00 178.00   1.00   17.50    --  111.00  30.00 -60.00   95
 10  \w     38.00 141.00   1.00   17.50    --  111.00 -65.00-146.14  103
 11  \w     39.00 140.00   1.00   17.50    --  111.00 -61.00 -60.00  101
 12  \w     82.00 178.00   1.00   17.50    --  111.00  61.00 -60.00   96
 13  \w     36.00 143.00   1.00   17.50    --  111.00 -73.00 135.33  107
 14  \w     83.00 178.00   1.00   17.50    --  111.00  30.00   0.00   95
 15  \w    100.00 178.00   1.00   17.50    --  111.00 111.00-180.00   78
 16  \w     35.00 116.00   1.00   17.50    --  111.00-111.00  30.00   81
 17  \w     37.00 136.00   1.00   17.50    --  111.00 -39.00 -18.33   99
 18  \w     35.00 116.00   1.00   17.50    --  111.00-111.00 -90.00   81
 19  \w    100.00 178.00   1.00   17.50    --  111.00 111.00-150.00   78
 20  \w     35.00 116.00   1.00   17.50    --  111.00-111.00-120.00   81
 21  \w     85.00 178.00   1.00   17.50    --  111.00  45.00 -60.00   93
 22  \w     28.00 109.00   1.00   17.50    --  111.00 -94.00-150.00   81
 23  \w     31.00 111.00   1.00   17.50    --  111.00-100.00  95.00   80
 24  \w     35.00 116.00   1.00   17.50    --  111.00-111.00-180.00   81
 25  \w     58.00 178.00   1.00   17.50    --  111.00  15.00-180.00  120
 26  \w     38.00 137.00   1.00   17.50    --  111.00 -45.00 -60.00   99
 27  \w     35.00 116.00   1.00   17.50    --  111.00-111.00  90.00   81
 28  \w     28.00 109.00   1.00   17.50    --  111.00 -94.00 120.00   81
 29  \w     35.00 116.00   1.00   17.50    --  111.00-111.00 -30.00   81
 30  \w     35.00 116.00   1.00   17.50    --  111.00-111.00-150.00   81
 31  \w     38.00 137.00   1.00   17.50    --  111.00 -45.00  90.00   99
 32  \w     23.00 178.00   1.00   17.50    --  111.00   0.00 -90.00  155
 33  \w     83.00 178.00   1.00   17.50    --  111.00  30.00  60.00   95
 34  \w     35.00 139.00   1.00   17.50    --  111.00 -30.00 150.00  104
 35  \w     35.00 144.00   1.00   17.50    --  111.00 -77.00 -60.00  109
 36  \w     35.00 144.00   1.00   17.50    --  111.00 -77.00 150.00  109
 37  \w     35.00 116.00   1.00   17.50    --  111.00-111.00 150.00   81
 38  \w     38.00 137.00   1.00   17.50    --  111.00 -45.00 -90.00   99
 39  \w     29.00 164.00   1.00   17.50    --  111.00 -15.00  90.00  135
 40  \w     37.00 142.00   1.00   17.50    --  111.00 -72.00 102.51  105
 41  \w     28.00 109.00   1.00   17.50    --  111.00 -94.00 -90.00   81
 42  \w     32.00 109.00   1.00   17.50    --  111.00 -94.00   0.00   77
 43  \w    102.00 145.00   1.00   17.50    --  111.00 -85.00 -92.21   43
 44  \w     87.00 123.00   1.00   17.50    --  111.00  45.00 -90.00   36
 45  \w    141.00 171.00   1.00   17.50    --  111.00  45.00 -90.00   30
 46  \w    105.00 142.00   1.00   17.50    --  111.00 178.00-150.00   37
 47  \w     51.00 120.00   1.00   17.50    --  111.00 -48.00 134.98   69
 48  \w     34.00  93.00   1.00   17.50    --  111.00 -85.00 -92.21   59
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0747518000
_diffrn_orient_matrix_UB_12      0.0668136000
_diffrn_orient_matrix_UB_13      0.0147681000
_diffrn_orient_matrix_UB_21      0.0453587000
_diffrn_orient_matrix_UB_22      0.0922651000
_diffrn_orient_matrix_UB_23      -0.0439606000
_diffrn_orient_matrix_UB_31      -0.0285855000
_diffrn_orient_matrix_UB_32      -0.0283156000
_diffrn_orient_matrix_UB_33      -0.1082633000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0861
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            72177
_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         71.014
_diffrn_reflns_theta_min         4.275
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    8.764
_exptl_absorpt_correction_T_max  0.569
_exptl_absorpt_correction_T_min  0.282
_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 violet'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.715
_exptl_crystal_description       block
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.257
_exptl_crystal_size_mid          0.084
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.153
_refine_diff_density_min         -0.683
_refine_diff_density_rms         0.126
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.237
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2779
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.237
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0615
_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/[\s^2^(Fo^2^)+(0.0311P)^2^+15.7442P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1453
_refine_ls_wR_factor_ref         0.1454
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2777
_reflns_number_total             2779
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc04248c2.cif
_cod_data_source_block           serc114-r2-rf
_cod_depositor_comments
'Adding full bibliography for 1565368--1565385.cif.'
_cod_original_formula_sum        'C13.50 H7 Cl4 N2 S'
_cod_database_code               1565383
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'S1 N2 Cl4 C13.5 H8'
_chemical_oxdiff_usercomment     'ABS-410 100K'
_reflns_odcompleteness_completeness 99.90
_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
2. Others
 Fixed Sof: H14A(0.5) H14B(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C7(H7), C6(H6), C12(H12)
;
_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 1.406
_oxdiff_exptl_absorpt_empirical_full_min 0.781