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_1565384
_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 S'
_chemical_formula_sum            'C14 H8 Cl4 N2 S'
_chemical_formula_weight         378.08
_chemical_properties_physical    Moisture-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-06-23
_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                 98.513(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0246(3)
_cell_length_b                   13.7857(5)
_cell_length_c                   12.0756(4)
_cell_measurement_reflns_used    37692
_cell_measurement_temperature    100.0(6)
_cell_measurement_theta_max      75.7670
_cell_measurement_theta_min      3.6390
_cell_volume                     1485.78(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 5.2774
_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     -1.00  25.00   1.00    5.00    --   38.00  95.00 -26.00   26
  2  \w      6.00  34.00   1.00    5.00    --   42.00  87.00-137.12   28
  3  \w   -114.00 -14.00   1.00    5.00    --  -42.08 -57.00-180.00  100
  4  \w   -116.00 -18.00   1.00    5.00    --  -42.08 -38.00  60.00   98
  5  \w    -67.00  32.00   1.00    5.00    --  -42.08  38.00-120.00   99
  6  \w   -116.00 -18.00   1.00    5.00    --  -42.08 -38.00 -90.00   98
  7  \w     23.00  98.00   1.00    5.00    --   42.08-125.00   0.00   75
  8  \w     23.00  98.00   1.00    5.00    --   42.08-125.00 150.00   75
  9  \w     16.00  45.00   1.00    5.00    --   50.00  82.00 123.54   29
 10  \w     17.00  46.00   1.00    5.00    --   50.00  80.00 -25.04   29
 11  \w     20.00  46.00   1.00    5.00    --   54.00  81.00-124.45   26
 12  \w     20.00  46.00   1.00    5.00    --   54.00  81.00  62.43   26
 13  \w     25.00 134.00   1.00    5.00    --   58.00  77.00  21.36  109
 14  \w     29.00 138.00   1.00    5.00    --   62.00  77.00 114.13  109
 15  \w     30.00 138.00   1.00    5.00    --   62.00  76.00 154.66  108
 16  \w     33.00 142.00   1.00    5.00    --   66.00  77.00-172.27  109
 17  \w     33.00 142.00   1.00    5.00    --   66.00  77.00 -44.94  109
 18  \w     38.00 146.00   1.00    5.00    --   70.00  76.00  34.91  108
 19  \w     38.00 146.00   1.00    5.00    --   70.00  76.00-137.16  108
 20  \w     38.00 146.00   1.00    5.00    --   70.00  76.00 -91.12  108
 21  \w     38.00 146.00   1.00    5.00    --   70.00  76.00 -15.51  108
 22  \w     78.00 178.00   1.00   20.00    --  111.00  77.00-180.00  100
 23  \w     82.00 178.00   1.00   20.00    --  111.00  61.00-150.00   96
 24  \w     78.00 178.00   1.00   20.00    --  111.00  77.00 -30.00  100
 25  \w     82.00 178.00   1.00   20.00    --  111.00  61.00  90.00   96
 26  \w     82.00 178.00   1.00   20.00    --  111.00  61.00 -30.00   96
 27  \w     82.00 178.00   1.00   20.00    --  111.00  61.00 -90.00   96
 28  \w     82.00 178.00   1.00   20.00    --  111.00  61.00-180.00   96
 29  \w     35.00 116.00   1.00   20.00    --  111.00-111.00 -90.00   81
 30  \w     78.00 178.00   1.00   20.00    --  111.00  77.00  90.00  100
 31  \w    100.00 178.00   1.00   20.00    --  111.00 111.00  30.00   78
 32  \w     35.00 116.00   1.00   20.00    --  111.00-111.00 120.00   81
 33  \w     78.00 178.00   1.00   20.00    --  111.00  77.00 -60.00  100
 34  \w     82.00 178.00   1.00   20.00    --  111.00  61.00  30.00   96
 35  \w     78.00 178.00   1.00   20.00    --  111.00  77.00   0.00  100
 36  \w     78.00 178.00   1.00   20.00    --  111.00  77.00-120.00  100
 37  \w     35.00 116.00   1.00   20.00    --  111.00-111.00   0.00   81
 38  \w     82.00 178.00   1.00   20.00    --  111.00  61.00 150.00   96
 39  \w     78.00 178.00   1.00   20.00    --  111.00  77.00-150.00  100
 40  \w     82.00 178.00   1.00   20.00    --  111.00  61.00  60.00   96
 41  \w     78.00 178.00   1.00   20.00    --  111.00  77.00  60.00  100
 42  \w     82.00 178.00   1.00   20.00    --  111.00  61.00 120.00   96
 43  \w     78.00 178.00   1.00   20.00    --  111.00  77.00 120.00  100
 44  \w     82.00 178.00   1.00   20.00    --  111.00  61.00   0.00   96
 45  \w     28.00 109.00   1.00   20.00    --  111.00 -94.00-180.00   81
 46  \w     78.00 178.00   1.00   20.00    --  111.00  77.00 150.00  100
 47  \w     35.00 116.00   1.00   20.00    --  111.00-111.00 -30.00   81
 48  \w     78.00 178.00   1.00   20.00    --  111.00  77.00  30.00  100
 49  \w     35.00 116.00   1.00   20.00    --  111.00-111.00  30.00   81
 50  \w     82.00 178.00   1.00   20.00    --  111.00  61.00 -60.00   96
 51  \w     38.00 137.00   1.00   20.00    --  111.00 -45.00  30.00   99
 52  \w     28.00 109.00   1.00   20.00    --  111.00 -94.00-150.00   81
 53  \w     35.00 144.00   1.00   20.00    --  111.00 -77.00  30.00  109
 54  \w     78.00 178.00   1.00   20.00    --  111.00  77.00 -90.00  100
 55  \w      7.00  35.00   1.00    5.00    --   42.00  86.00  79.66   28
 56  \w   -114.00 -14.00   1.00    5.00    --  -42.08 -57.00 120.00  100
 57  \w     11.00 116.00   1.00    5.00    --   42.08  70.00 142.30  105
 58  \w     16.00  45.00   1.00    5.00    --   50.00  82.00-163.20   29
 59  \w     21.00  49.00   1.00    5.00    --   54.00  78.00 -75.62   28
 60  \w     20.00  46.00   1.00    5.00    --   54.00  81.00 -55.32   26
 61  \w     20.00  46.00   1.00    5.00    --   54.00  81.00 104.84   26
 62  \w     25.00 134.00   1.00    5.00    --   58.00  77.00 -71.09  109
 63  \w     26.00 133.00   1.00    5.00    --   58.00  75.00   6.09  107
 64  \w     26.00 133.00   1.00    5.00    --   58.00  75.00 110.06  107
 65  \w     25.00 134.00   1.00    5.00    --   58.00  77.00-132.01  109
 66  \w     30.00 138.00   1.00    5.00    --   62.00  76.00-107.44  108
 67  \w     30.00 137.00   1.00    5.00    --   62.00  75.00  33.64  107
 68  \w     30.00 137.00   1.00    5.00    --   62.00  75.00-135.39  107
 69  \w     30.00 137.00   1.00    5.00    --   62.00  75.00  79.94  107
 70  \w     34.00 142.00   1.00    5.00    --   66.00  76.00 -67.40  108
;
_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      -0.1599030000
_diffrn_orient_matrix_UB_12      0.0129340000
_diffrn_orient_matrix_UB_13      0.0276028000
_diffrn_orient_matrix_UB_21      0.0535925000
_diffrn_orient_matrix_UB_22      -0.0329002000
_diffrn_orient_matrix_UB_23      0.1214787000
_diffrn_orient_matrix_UB_31      0.0358979000
_diffrn_orient_matrix_UB_32      0.1059595000
_diffrn_orient_matrix_UB_33      0.0343349000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0805
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            54843
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.067
_diffrn_reflns_theta_min         3.701
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    8.491
_exptl_absorpt_correction_T_max  0.722
_exptl_absorpt_correction_T_min  0.328
_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    1.690
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.216
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.048
_refine_diff_density_max         1.102
_refine_diff_density_min         -0.693
_refine_diff_density_rms         0.128
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.06(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         5617
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0766
_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^)+(0.1760P)^2^+0.9125P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2049
_refine_ls_wR_factor_ref         0.2058
_reflns_Friedel_coverage         0.878
_reflns_Friedel_fraction_full    0.964
_reflns_Friedel_fraction_max     0.959
_reflns_number_gt                5556
_reflns_number_total             5617
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc04248c2.cif
_cod_data_source_block           serc118-r1-fm-non-equiv-rf1
_cod_depositor_comments
;
Adding full bibliography for 1565368--1565385.cif.

2022-05-30
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C28 H16 Cl8 N4 S2'
_cod_original_formula_weight         756.17
_cod_original_formula_moiety         '2(C14 H8 Cl4 N2 S)'
_cod_original_formula_units_Z            2
_cod_database_code               1565384
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C28 N4 S2 Cl8 H14'
_chemical_oxdiff_usercomment     ABS-295
_reflns_odcompleteness_completeness 99.96
_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.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C27(H27), C7(H7), C5(H5), C19(H19), C21(H21), C18(H18), C4(H4),
 C20(H20), C6(H6)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C22(H22A,H22B,H22C)
;
_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 2.373
_oxdiff_exptl_absorpt_empirical_full_min 0.432