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_1565368
_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 H9.96 Cl4.04 N2 S'
_chemical_formula_sum            'C15 H9.97 Cl4.03 N2 S'
_chemical_formula_weight         393.31
_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             2018-06-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_audit_update_record
;
2021-08-03 deposited with the CCDC.	2021-11-23 downloaded from the CCDC.
;
_cell_angle_alpha                80.349(3)
_cell_angle_beta                 86.679(3)
_cell_angle_gamma                72.338(3)
_cell_formula_units_Z            2
_cell_length_a                   7.3043(3)
_cell_length_b                   9.0923(3)
_cell_length_c                   12.6109(5)
_cell_measurement_reflns_used    10009
_cell_measurement_temperature    100.0(5)
_cell_measurement_theta_max      75.6800
_cell_measurement_theta_min      5.1490
_cell_volume                     786.73(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   -115.00 -20.00   1.00    1.00    --  -42.45 -38.00  60.00   95
  2  \w    -79.00  36.00   1.00    1.00    --  -42.45  19.00-120.00  115
  3  \w      1.00  82.00   1.00    1.00    --   42.45 -99.00 -60.00   81
  4  \w     23.00  97.00   1.00    1.00    --   42.45-125.00  30.00   74
  5  \w     23.00  97.00   1.00    1.00    --   42.45-125.00 -90.00   74
  6  \w     30.00 109.00   1.00    2.50    --  111.00 -94.00-150.00   79
  7  \w    100.00 178.00   1.00    2.50    --  111.00 111.00-150.00   78
  8  \w    100.00 178.00   1.00    2.50    --  111.00 111.00 -60.00   78
  9  \w     36.00 116.00   1.00    2.50    --  111.00-111.00 -30.00   80
 10  \w     36.00 116.00   1.00    2.50    --  111.00-111.00-180.00   80
 11  \w     37.00 142.00   1.00    2.50    --  111.00 -77.00   0.00  105
 12  \w     30.00 109.00   1.00    2.50    --  111.00 -94.00  60.00   79
 13  \w     40.00 135.00   1.00    2.50    --  111.00 -45.00  30.00   95
 14  \w     41.00 139.00   1.00    2.50    --  111.00 -61.00 -60.00   98
 15  \w     36.00 135.00   1.00    2.50    --  111.00 -30.00-180.00   99
 16  \w     83.00 178.00   1.00    2.50    --  111.00  61.00   0.00   95
 17  \w     37.00 142.00   1.00    2.50    --  111.00 -77.00-120.00  105
 18  \w     36.00 116.00   1.00    2.50    --  111.00-111.00   0.00   80
 19  \w     66.00 178.00   1.00    2.50    --  111.00  15.00  90.00  112
 20  \w     66.00 178.00   1.00    2.50    --  111.00  15.00-180.00  112
 21  \w     36.00 116.00   1.00    2.50    --  111.00-111.00  90.00   80
 22  \w     37.00 142.00   1.00    2.50    --  111.00 -77.00 120.00  105
 23  \w   -116.00 -11.00   1.00    1.00    --  -42.45 -77.00  90.00  105
 24  \w    -65.00  30.00   1.00    1.00    --  -42.45  38.00 120.00   95
 25  \w   -113.00 -16.00   1.00    1.00    --  -42.45 -57.00-120.00   97
 26  \w   -116.00 -11.00   1.00    1.00    --  -42.45 -77.00   0.00  105
 27  \w   -113.00 -16.00   1.00    1.00    --  -42.45 -57.00 150.00   97
 28  \w     87.00 178.00   1.00    2.50    --  111.00  45.00-150.00   91
 29  \w     83.00 178.00   1.00    2.50    --  111.00  61.00 120.00   95
 30  \w     66.00 178.00   1.00    2.50    --  111.00  15.00 -60.00  112
 31  \w     80.00 178.00   1.00    2.50    --  111.00  77.00 -90.00   98
 32  \w     80.00 178.00   1.00    2.50    --  111.00  77.00  60.00   98
 33  \w     80.00 178.00   1.00    2.50    --  111.00  77.00 150.00   98
 34  \w     83.00 178.00   1.00    2.50    --  111.00  61.00-120.00   95
 35  \w     80.00 178.00   1.00    2.50    --  111.00  77.00 -60.00   98
;
_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      0.0564637000
_diffrn_orient_matrix_UB_12      -0.0381698000
_diffrn_orient_matrix_UB_13      0.1195522000
_diffrn_orient_matrix_UB_21      0.0522881000
_diffrn_orient_matrix_UB_22      -0.1759623000
_diffrn_orient_matrix_UB_23      -0.0054536000
_diffrn_orient_matrix_UB_31      0.2075418000
_diffrn_orient_matrix_UB_32      -0.0025932000
_diffrn_orient_matrix_UB_33      -0.0321446000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0213
_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       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15042
_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         68.583
_diffrn_reflns_theta_min         3.555
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    8.097
_exptl_absorpt_correction_T_max  0.689
_exptl_absorpt_correction_T_min  0.272
_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    1.660
_exptl_crystal_description       block
_exptl_crystal_F_000             397
_exptl_crystal_size_max          0.267
_exptl_crystal_size_mid          0.168
_exptl_crystal_size_min          0.053
_refine_diff_density_max         1.290
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2891
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0360
_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^)+(0.0510P)^2^+0.9320P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.0950
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2792
_reflns_number_total             2891
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc04248c2.cif
_cod_data_source_block           serc233-r1-rf
_cod_depositor_comments
'Adding full bibliography for 1565368--1565385.cif.'
_cod_database_code               1565368
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'S1 N2 Cl4 C15 H20'
_chemical_oxdiff_usercomment     ABS-416
_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
2. Others
 Sof(H6)=1-FVAR(1)
 Sof(Cl5)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B)
3.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C15(H15), C14(H14), C12(H12), C13(H13)
;
_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 1.482
_oxdiff_exptl_absorpt_empirical_full_min 0.714