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_1565385
_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         'C16 H12 Cl4 N2 S'
_chemical_formula_sum            'C16 H12 Cl4 N2 S'
_chemical_formula_weight         406.14
_chemical_properties_physical    Moisture-sensitive
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2018-06-13
_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                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_formula_units_Z            8
_cell_length_a                   14.2979(4)
_cell_length_b                   14.0607(3)
_cell_length_c                   16.3174(4)
_cell_measurement_reflns_used    39392
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.0870
_cell_measurement_theta_min      3.8700
_cell_volume                     3280.43(14)
_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)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_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    -68.00  29.00   1.00    8.00    --  -41.51  57.00  90.00   97
  2  \w   -112.00 -15.00   1.00    8.00    --  -41.51 -57.00 -60.00   97
  3  \w   -114.00 -19.00   1.00    8.00    --  -41.51 -38.00  30.00   95
  4  \w    -64.00  31.00   1.00    8.00    --  -41.51  38.00-150.00   95
  5  \w     19.00 114.00   1.00    8.00    --   41.51  38.00 -90.00   95
  6  \w     23.00  97.00   1.00    8.00    --   41.51-125.00 120.00   74
  7  \w      1.00  81.00   1.00    8.00    --   41.51 -99.00 -60.00   80
  8  \w     30.00 109.00   1.00   20.00    --  111.00 -95.00 150.00   79
  9  \w     36.00 116.00   1.00   20.00    --  111.00-111.00  60.00   80
 10  \w     32.00 152.00   1.00   20.00    --  111.00 -17.00 -33.79  120
 11  \w     37.00 142.00   1.00   20.00    --  111.00 -77.00 -30.00  105
 12  \w     87.00 178.00   1.00   20.00    --  111.00  30.00-150.00   91
 13  \w     36.00 116.00   1.00   20.00    --  111.00-111.00 -60.00   80
 14  \w     87.00 178.00   1.00   20.00    --  111.00  30.00-180.00   91
 15  \w     36.00 116.00   1.00   20.00    --  111.00-111.00-120.00   80
 16  \w     57.00 151.00   1.00   20.00    --  111.00 178.00  60.00   94
 17  \w     36.00 116.00   1.00   20.00    --  111.00-111.00 120.00   80
 18  \w     36.00 116.00   1.00   20.00    --  111.00-111.00   0.00   80
 19  \w     37.00 142.00   1.00   20.00    --  111.00 -77.00-150.00  105
 20  \w     87.00 178.00   1.00   20.00    --  111.00  45.00-120.00   91
 21  \w     41.00 139.00   1.00   20.00    --  111.00 -61.00 -90.00   98
 22  \w     30.00 109.00   1.00   20.00    --  111.00 -95.00-180.00   79
 23  \w     50.00 120.00   1.00   20.00    --  111.00 -30.00-120.00   70
 24  \w     70.00 101.00   1.00   20.00    --  111.00 -95.00   0.00   31
 25  \w     70.00 112.00   1.00   20.00    --  111.00 -30.00   0.00   42
 26  \w    109.00 136.00   1.00   20.00    --  111.00  45.00 -60.00   27
 27  \w    107.00 175.00   1.00   20.00    --  111.00 111.00 -90.00   68
 28  \w     36.00  85.00   1.00   20.00    --  111.00 -30.00 150.00   49
 29  \w    153.00 178.00   1.00   20.00    --  111.00  15.00 -60.00   25
 30  \w     76.00 103.00   1.00   20.00    --  111.00 -95.00  60.00   27
 31  \w     83.00 122.00   1.00   20.00    --  111.00  15.00 -60.00   39
 32  \w     39.00 107.00   1.00   20.00    --  111.00 -95.00  30.00   68
 33  \w     54.00  81.00   1.00   20.00    --  111.00 -95.00 -60.00   27
 34  \w     33.00  85.00   1.00   20.00    --  111.00 -20.00 -42.64   52
 35  \w     84.00 131.00   1.00   20.00    --  111.00  61.00 -90.00   47
 36  \w     49.00  74.00   1.00   20.00    --  111.00-111.00-150.00   25
 37  \w     84.00 116.00   1.00   20.00    --  111.00-111.00-150.00   32
 38  \w     91.00 135.00   1.00   20.00    --  111.00 -45.00 -60.00   44
 39  \w    116.00 161.00   1.00   20.00    --  111.00  45.00  30.00   45
 40  \w     43.00 123.00   1.00   20.00    --  111.00 -45.00 -90.00   80
 41  \w     94.00 126.00   1.00   20.00    --  111.00 -61.00  90.00   32
 42  \w     45.00 114.00   1.00   20.00    --  111.00-111.00 150.00   69
 43  \w    101.00 148.00   1.00   20.00    --  111.00 111.00 -60.00   47
 44  \w     59.00  86.00   1.00   20.00    --  111.00 -77.00   0.00   27
 45  \w     91.00 118.00   1.00   20.00    --  111.00 -77.00   0.00   27
 46  \w     92.00 125.00   1.00   20.00    --  111.00 -77.00  90.00   33
 47  \w    108.00 141.00   1.00   20.00    --  111.00 -77.00 120.00   33
 48  \w     72.00  99.00   1.00   20.00    --  111.00  15.00 -90.00   27
 49  \w    142.00 167.00   1.00   20.00    --  111.00  15.00 -90.00   25
 50  \w    143.00 173.00   1.00   20.00    --  111.00 111.00-150.00   30
 51  \w     34.00  73.00   1.00   20.00    --  111.00 -95.00 120.00   39
 52  \w     89.00 116.00   1.00   20.00    --  111.00-111.00 -30.00   27
 53  \w     88.00 115.00   1.00   20.00    --  111.00-111.00  30.00   27
 54  \w     93.00 137.00   1.00   20.00    --  111.00 -58.00 -49.38   44
 55  \w    118.00 145.00   1.00   20.00    --  111.00  45.00  90.00   27
 56  \w    151.00 176.00   1.00   20.00    --  111.00  30.00  90.00   25
 57  \w     67.00 132.00   1.00   20.00    --  111.00 -40.00 131.86   65
;
_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      0.0908567000
_diffrn_orient_matrix_UB_12      -0.0005808000
_diffrn_orient_matrix_UB_13      -0.0508554000
_diffrn_orient_matrix_UB_21      -0.0550263000
_diffrn_orient_matrix_UB_22      0.0350278000
_diffrn_orient_matrix_UB_23      -0.0754912000
_diffrn_orient_matrix_UB_31      0.0187307000
_diffrn_orient_matrix_UB_32      0.1035064000
_diffrn_orient_matrix_UB_33      0.0255292000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0724
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            63211
_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         71.270
_diffrn_reflns_theta_min         5.178
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    7.736
_exptl_absorpt_correction_T_max  0.404
_exptl_absorpt_correction_T_min  0.107
_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            'clear orangish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_description       block
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.424
_exptl_crystal_size_mid          0.235
_exptl_crystal_size_min          0.177
_refine_diff_density_max         0.997
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3183
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0399
_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/[\s^2^(Fo^2^)+(0.0369P)^2^+6.1544P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.0977
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3176
_reflns_number_total             3183
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc04248c2.cif
_cod_data_source_block           serc086-r1-rf3
_cod_depositor_comments
'Adding full bibliography for 1565368--1565385.cif.'
_cod_original_cell_volume        3280.41(15)
_cod_database_code               1565385
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C16 H12 Cl4 N2 S1 '
_chemical_oxdiff_usercomment     'ABS-259 2,3-2-Me-Cl'
_cell_oxdiff_angle_alpha         90.190(2)
_cell_oxdiff_angle_beta          90.074(2)
_cell_oxdiff_angle_gamma         89.788(3)
_cell_oxdiff_length_a            14.2814(5)
_cell_oxdiff_length_b            14.0999(4)
_cell_oxdiff_length_c            16.2910(4)
_cell_oxdiff_measurement_reflns_used 39480
_cell_oxdiff_volume              3280.41(17)
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
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 1.580
_oxdiff_exptl_absorpt_empirical_full_min 0.638