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_1565381
_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  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -66.00  32.00   1.00    1.50    --  -41.91  38.00-150.00   98
  2  \w   -116.00 -17.00   1.00    1.50    --  -41.91 -38.00  30.00   99
  3  \w    -96.00  -2.00   1.00    1.50    --  -41.91 125.00 -60.00   94
  4  \w    -32.00  66.00   1.00    1.50    --   41.91 -38.00-120.00   98
  5  \w     23.00  98.00   1.00    1.50    --   41.91-125.00 -90.00   75
  6  \w     37.00 117.00   1.00    3.00    --  112.00-115.00 -46.00   80
  7  \w     84.00 178.00   1.00    3.00    --  112.00  30.00-120.00   94
  8  \w     36.00 145.00   1.00    3.00    --  112.00 -77.00 -90.00  109
  9  \w     29.00 109.00   1.00    3.00    --  112.00 -94.00-150.00   80
 10  \w     36.00 140.00   1.00    3.00    --  112.00 -30.00 -90.00  104
 11  \w     57.00 151.00   1.00    3.00    --  112.00 178.00 -90.00   94
 12  \w     36.00 116.00   1.00    3.00    --  112.00-111.00   0.00   80
 13  \w     29.00 109.00   1.00    3.00    --  112.00 -94.00  60.00   80
 14  \w     29.00 109.00   1.00    3.00    --  112.00 -94.00 120.00   80
 15  \w    100.00 178.00   1.00    3.00    --  112.00 111.00   0.00   78
 16  \w     36.00 116.00   1.00    3.00    --  112.00-111.00  90.00   80
 17  \w     79.00 178.00   1.00    3.00    --  112.00  77.00   0.00   99
 18  \w    100.00 178.00   1.00    3.00    --  112.00 111.00  60.00   78
 19  \w     29.00 109.00   1.00    3.00    --  112.00 -94.00 -90.00   80
 20  \w     86.00 178.00   1.00    3.00    --  112.00  45.00 150.00   92
 21  \w     39.00 138.00   1.00    3.00    --  112.00 -45.00  60.00   99
 22  \w    100.00 178.00   1.00    3.00    --  112.00 111.00-150.00   78
 23  \w     59.00 178.00   1.00    3.00    --  112.00  15.00 -30.00  119
 24  \w   -118.00  -9.00   1.00    1.50    --  -41.91 -77.00-150.00  109
 25  \w   -118.00  -9.00   1.00    1.50    --  -41.91 -77.00  30.00  109
 26  \w   -118.00  -9.00   1.00    1.50    --  -41.91 -77.00 -60.00  109
 27  \w     64.00 124.00   1.00    1.50    --   41.91 170.00-173.00   60
 28  \w      9.00 118.00   1.00    1.50    --   41.91  77.00-150.00  109
 29  \w     14.00 114.00   1.00    1.50    --   41.91  57.00 150.00  100
 30  \w     84.00 178.00   1.00    3.00    --  112.00  30.00  90.00   94
 31  \w     83.00 178.00   1.00    3.00    --  112.00  61.00-120.00   95
 32  \w     79.00 178.00   1.00    3.00    --  112.00  77.00 -90.00   99
 33  \w     79.00 178.00   1.00    3.00    --  112.00  77.00  30.00   99
 34  \w     83.00 178.00   1.00    3.00    --  112.00  61.00 -30.00   95
 35  \w     79.00 178.00   1.00    3.00    --  112.00  77.00  90.00   99
 36  \w     79.00 130.00   1.00    3.00    --  112.00  77.00  60.00   51
 37  \w     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       '\w 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/[\s^2^(Fo^2^)+36.6427P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(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'
_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