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_1565376
_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         'C15 H10 Cl4 N2 S'
_chemical_formula_sum            'C15 H10 Cl4 N2 S'
_chemical_formula_weight         392.11
_chemical_properties_physical    Moisture-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-06-18
_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                 96.598(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.38990(10)
_cell_length_b                   10.5325(2)
_cell_length_c                   20.5855(4)
_cell_measurement_reflns_used    10953
_cell_measurement_temperature    100.0(5)
_cell_measurement_theta_max      75.2570
_cell_measurement_theta_min      4.7080
_cell_volume                     1591.64(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   -113.00 -16.00   1.00    3.00    --  -42.70 -57.00  90.00   97
  2  \w    -69.00  27.00   1.00    3.00    --  -42.70  57.00-120.00   96
  3  \w    -65.00  30.00   1.00    3.00    --  -42.70  38.00  30.00   95
  4  \w      1.00  83.00   1.00    3.00    --   42.70 -99.00  30.00   82
  5  \w      1.00  83.00   1.00    3.00    --   42.70 -99.00 -60.00   82
  6  \w     31.00 156.00   1.00   12.50    --  111.00 -15.00   0.00  125
  7  \w     36.00 116.00   1.00   12.50    --  111.00-111.00-150.00   80
  8  \w     87.00 178.00   1.00   12.50    --  111.00  45.00  90.00   91
  9  \w     66.00 178.00   1.00   12.50    --  111.00  15.00-120.00  112
 10  \w    100.00 178.00   1.00   12.50    --  111.00 111.00 -90.00   78
 11  \w     87.00 178.00   1.00   12.50    --  111.00  45.00-180.00   91
 12  \w    100.00 178.00   1.00   12.50    --  111.00 111.00-150.00   78
 13  \w     36.00 116.00   1.00   12.50    --  111.00-111.00 -90.00   80
 14  \w     30.00 109.00   1.00   12.50    --  111.00 -94.00 -30.00   79
 15  \w     37.00 116.00   1.00   12.50    --  111.00-111.00  60.00   79
 16  \w     71.00 116.00   1.00   12.50    --  111.00-111.00 -30.00   45
 17  \w     52.00  83.00   1.00   12.50    --  111.00 -45.00 150.00   31
 18  \w     90.00 116.00   1.00   12.50    --  111.00-111.00 150.00   26
 19  \w    116.00 176.00   1.00   12.50    --  111.00 111.00  30.00   60
 20  \w     42.00  86.00   1.00   12.50    --  111.00 -45.00   0.00   44
 21  \w     94.00 135.00   1.00   12.50    --  111.00 -45.00   0.00   41
 22  \w     60.00  87.00   1.00   12.50    --  111.00 -94.00-150.00   27
 23  \w     31.00  69.00   1.00   12.50    --  111.00 -94.00 -60.00   38
 24  \w     31.00  60.00   1.00   12.50    --  111.00 -94.00  30.00   29
 25  \w     98.00 125.00   1.00   12.50    --  111.00  45.00 120.00   27
 26  \w    148.00 175.00   1.00   12.50    --  111.00  45.00 120.00   27
 27  \w     69.00 108.00   1.00   12.50    --  111.00 -77.00  30.00   39
 28  \w     69.00 107.00   1.00   12.50    --  111.00 -94.00 120.00   38
 29  \w     58.00 114.00   1.00   12.50    --  111.00-111.00  30.00   56
 30  \w     88.00 178.00   1.00   12.50    --  111.00  45.00   0.00   90
;
_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      0.0334482000
_diffrn_orient_matrix_UB_12      -0.0326049000
_diffrn_orient_matrix_UB_13      0.0733706000
_diffrn_orient_matrix_UB_21      0.0141451000
_diffrn_orient_matrix_UB_22      0.1425241000
_diffrn_orient_matrix_UB_23      0.0166349000
_diffrn_orient_matrix_UB_31      -0.2066450000
_diffrn_orient_matrix_UB_32      0.0045270000
_diffrn_orient_matrix_UB_33      0.0042072000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            19045
_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         73.489
_diffrn_reflns_theta_min         4.324
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    7.949
_exptl_absorpt_correction_T_max  0.793
_exptl_absorpt_correction_T_min  0.317
_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 orange'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_description       needle
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.377
_exptl_crystal_size_mid          0.042
_exptl_crystal_size_min          0.038
_refine_diff_density_max         1.262
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3201
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0456
_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^)+(0.0552P)^2^+3.3699P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1183
_refine_ls_wR_factor_ref         0.1198
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3031
_reflns_number_total             3201
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc04248c2.cif
_cod_data_source_block           serc256-r1-rf
_cod_depositor_comments
'Adding full bibliography for 1565368--1565385.cif.'
_cod_database_code               1565376
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'S1 N2 Cl4 C15 H10'
_chemical_oxdiff_usercomment     ABS-551
_reflns_odcompleteness_completeness 99.97
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C3(H3), C6(H6), C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_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 1.363
_oxdiff_exptl_absorpt_empirical_full_min 0.597