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_1565369
_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         'C14 H8 Cl4 N2 O S'
_chemical_formula_sum            'C14 H8 Cl4 N2 O S'
_chemical_formula_weight         394.08
_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     direct
_audit_creation_date             2017-08-16
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5289)
;
_audit_update_record
;
2021-08-03 deposited with the CCDC.	2021-11-23 downloaded from the CCDC.
;
_cell_angle_alpha                83.2406(19)
_cell_angle_beta                 78.4301(19)
_cell_angle_gamma                71.106(2)
_cell_formula_units_Z            2
_cell_length_a                   7.10603(16)
_cell_length_b                   7.22142(17)
_cell_length_c                   15.6955(4)
_cell_measurement_reflns_used    10470
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.0600
_cell_measurement_theta_min      2.8610
_cell_volume                     745.33(3)
_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      100.00(10)
_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 -16.00   1.00    1.00    --  -40.37 -38.00-150.00   99
  2  \w    -73.00  36.00   1.00    1.00    --  -40.37  77.00 -30.00  109
  3  \w   -115.00 -16.00   1.00    1.00    --  -40.37 -38.00 120.00   99
  4  \w      1.00  81.00   1.00    1.00    --   40.37 -99.00  90.00   80
  5  \w      1.00  81.00   1.00    1.00    --   40.37 -99.00  60.00   80
  6  \w     23.00  96.00   1.00    1.00    --   40.37-125.00-150.00   73
  7  \w     29.00 109.00   1.00    1.00    --  112.00 -94.00  60.00   80
  8  \w     86.00 178.00   1.00    1.00    --  112.00  45.00 -60.00   92
  9  \w     86.00 178.00   1.00    1.00    --  112.00  45.00-180.00   92
 10  \w     86.00 178.00   1.00    1.00    --  112.00  45.00-150.00   92
 11  \w     36.00 116.00   1.00    1.00    --  112.00-111.00 -90.00   80
 12  \w     36.00 145.00   1.00    1.00    --  112.00 -77.00 120.00  109
 13  \w    100.00 178.00   1.00    1.00    --  112.00 111.00 120.00   78
 14  \w     36.00 116.00   1.00    1.00    --  112.00-111.00 120.00   80
 15  \w     40.00 141.00   1.00    1.00    --  112.00 -61.00-120.00  101
 16  \w    100.00 178.00   1.00    1.00    --  112.00 111.00 150.00   78
 17  \w     36.00 116.00   1.00    1.00    --  112.00-111.00   0.00   80
 18  \w     37.00 117.00   1.00    1.00    --  112.00-115.00-117.00   80
 19  \w     29.00 109.00   1.00    1.00    --  112.00 -94.00 -90.00   80
 20  \w     79.00 178.00   1.00    1.00    --  112.00  77.00-120.00   99
 21  \w   -115.00 -16.00   1.00    1.00    --  -40.37 -38.00 -60.00   99
 22  \w   -117.00  -8.00   1.00    1.00    --  -40.37 -77.00  90.00  109
 23  \w    -34.00  65.00   1.00    1.00    --   40.37 -38.00-150.00   99
 24  \w      8.00 117.00   1.00    1.00    --   40.37  77.00 -90.00  109
 25  \w      8.00 117.00   1.00    1.00    --   40.37  77.00   0.00  109
 26  \w      4.00  33.00   1.00    1.00    --   40.37  88.00-158.51   29
 27  \w     59.00 178.00   1.00    1.00    --  112.00  15.00  90.00  119
 28  \w     79.00 178.00   1.00    1.00    --  112.00  77.00   0.00   99
 29  \w     79.00 178.00   1.00    1.00    --  112.00  77.00 120.00   99
 30  \w     79.00 178.00   1.00    1.00    --  112.00  77.00 -60.00   99
 31  \w     79.00 178.00   1.00    1.00    --  112.00  77.00  60.00   99
 32  \w     86.00 178.00   1.00    1.00    --  112.00  45.00 120.00   92
 33  \w     79.00 178.00   1.00    1.00    --  112.00  77.00-150.00   99
 34  \w     79.00 178.00   1.00    1.00    --  112.00  77.00  30.00   99
 35  \w     83.00 178.00   1.00    1.00    --  112.00  61.00  90.00   95
 36  \w     83.00 178.00   1.00    1.00    --  112.00  61.00 150.00   95
 37  \w     79.00 178.00   1.00    1.00    --  112.00  77.00 -30.00   99
;
_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      0.2032564000
_diffrn_orient_matrix_UB_12      -0.1554607000
_diffrn_orient_matrix_UB_13      -0.0303672000
_diffrn_orient_matrix_UB_21      0.0413911000
_diffrn_orient_matrix_UB_22      -0.0354161000
_diffrn_orient_matrix_UB_23      0.0941725000
_diffrn_orient_matrix_UB_31      -0.1053473000
_diffrn_orient_matrix_UB_32      -0.1599522000
_diffrn_orient_matrix_UB_33      0.0167278000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0191
_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       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14538
_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         71.255
_diffrn_reflns_theta_min         2.878
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    8.544
_exptl_absorpt_correction_T_max  0.559
_exptl_absorpt_correction_T_min  0.202
_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 red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.756
_exptl_crystal_description       irregular
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.367
_exptl_crystal_size_mid          0.197
_exptl_crystal_size_min          0.115
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         2893
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0269
_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^)+(0.0504P)^2^+0.2877P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0769
_refine_ls_wR_factor_ref         0.0778
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2795
_reflns_number_total             2893
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc04248c2.cif
_cod_data_source_block           serc027-r1-rf
_cod_depositor_comments
'Adding full bibliography for 1565368--1565385.cif.'
_cod_database_code               1565369
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C14 N2 S1 Cl4 O1 H8'
_chemical_oxdiff_usercomment     ABS-092
_cell_oxdiff_angle_alpha         83.2406(19)
_cell_oxdiff_angle_beta          78.4301(19)
_cell_oxdiff_angle_gamma         71.106(2)
_cell_oxdiff_length_a            7.10603(16)
_cell_oxdiff_length_b            7.22142(17)
_cell_oxdiff_length_c            15.6955(4)
_cell_oxdiff_measurement_reflns_used 10470
_cell_oxdiff_volume              745.33(3)
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: C15(0.5) H15A(0.5) H15B(0.5) H15C(0.5) C14(0.5) H14A(0.5)
 H14B(0.5) H14C(0.5)
3.a Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C14(H14A,H14B,H14C)
;
_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 1.887
_oxdiff_exptl_absorpt_empirical_full_min 0.576