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_1565375
_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 H9.88 Cl4.12 N2 S'
_chemical_formula_sum            'C15 H9.88 Cl4.12 N2 S'
_chemical_formula_weight         396.33
_chemical_properties_physical    Moisture-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-06-27
_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                 105.795(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8074(3)
_cell_length_b                   15.8724(4)
_cell_length_c                   13.5003(4)
_cell_measurement_reflns_used    12836
_cell_measurement_temperature    100.0(6)
_cell_measurement_theta_max      74.5590
_cell_measurement_theta_min      4.3690
_cell_volume                     1609.82(9)
_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(6)
_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    -65.00  30.00   1.00   10.00    --  -42.45  38.00 -90.00   95
  2  \w   -113.00 -16.00   1.00   10.00    --  -42.45 -57.00 -30.00   97
  3  \w    -74.00  31.00   1.00   10.00    --  -42.45  77.00 -90.00  105
  4  \w    -69.00  28.00   1.00   10.00    --  -42.45  57.00 120.00   97
  5  \w     23.00  97.00   1.00   10.00    --   42.45-125.00-180.00   74
  6  \w     38.00 134.00   1.00   30.00    --  109.57 -45.00 150.00   96
  7  \w     28.00 109.00   1.00   30.00    --  109.57 -94.00  90.00   81
  8  \w     38.00 122.00   1.00   30.00    --  109.57-125.00 -90.00   84
  9  \w     36.00 141.00   1.00   30.00    --  109.57 -77.00 150.00  105
 10  \w     94.00 178.00   1.00   30.00    --  109.57 125.00 150.00   84
 11  \w     86.00 178.00   1.00   30.00    --  109.57  30.00-150.00   92
 12  \w     38.00 122.00   1.00   30.00    --  109.57-125.00  30.00   84
 13  \w     35.00 133.00   1.00   30.00    --  109.57 -30.00-120.00   98
 14  \w     98.00 178.00   1.00   30.00    --  109.57  85.00-140.00   80
 15  \w     94.00 178.00   1.00   30.00    --  109.57 125.00  60.00   84
 16  \w     86.00 178.00   1.00   30.00    --  109.57  30.00 120.00   92
 17  \w     38.00 134.00   1.00   30.00    --  109.57 -45.00  60.00   96
 18  \w   -113.00 -16.00   1.00   10.00    --  -42.45 -57.00-120.00   97
 19  \w   -116.00 -11.00   1.00   10.00    --  -42.45 -77.00-180.00  105
 20  \w   -113.00 -16.00   1.00   10.00    --  -42.45 -57.00  60.00   97
 21  \w   -116.00 -11.00   1.00   10.00    --  -42.45 -77.00  30.00  105
 22  \w      1.00  82.00   1.00   10.00    --   42.45 -99.00  30.00   81
 23  \w     86.00 178.00   1.00   30.00    --  109.57  30.00  60.00   92
 24  \w     64.00 178.00   1.00   30.00    --  109.57  15.00   0.00  114
 25  \w     82.00 178.00   1.00   30.00    --  109.57  61.00   0.00   96
 26  \w     82.00 178.00   1.00   30.00    --  109.57  61.00 150.00   96
 27  \w     86.00 178.00   1.00   30.00    --  109.57  30.00 -90.00   92
;
_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      0.0442674000
_diffrn_orient_matrix_UB_12      -0.0808354000
_diffrn_orient_matrix_UB_13      0.0650528000
_diffrn_orient_matrix_UB_21      -0.1225484000
_diffrn_orient_matrix_UB_22      0.0291048000
_diffrn_orient_matrix_UB_23      0.0656030000
_diffrn_orient_matrix_UB_31      -0.1582905000
_diffrn_orient_matrix_UB_32      -0.0451727000
_diffrn_orient_matrix_UB_33      -0.0743564000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22798
_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         67.907
_diffrn_reflns_theta_min         4.398
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    8.049
_exptl_absorpt_correction_T_max  0.833
_exptl_absorpt_correction_T_min  0.244
_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            'dark yellow'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.635
_exptl_crystal_description       trapezoid
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.315
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.163
_refine_diff_density_min         -0.735
_refine_diff_density_rms         0.117
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.318
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2931
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.318
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0744
_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^)+(0.0220P)^2^+12.6400P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1732
_refine_ls_wR_factor_ref         0.1733
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2898
_reflns_number_total             2931
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc04248c2.cif
_cod_data_source_block           serc211-r1-rf
_cod_depositor_comments
'Adding full bibliography for 1565368--1565385.cif.'
_cod_database_code               1565375
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'S1 N2 Cl4 C15 H10'
_chemical_oxdiff_usercomment
'ABS-284 - Recrystallised (Partial chlorination)'
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(Cl4)=1-FVAR(1)
 Sof(H10)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C14(H14)
3.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C3(H3), C7(H7), C4(H4), C6(H6), C5(H5)
3.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 1.425
_oxdiff_exptl_absorpt_empirical_full_min 0.603