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_1565374
_publ_section_title
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 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         'C16 H12 Cl4 N2 O S'
_chemical_formula_sum            'C16 H12 Cl4 N2 O S'
_chemical_formula_weight         422.14
_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   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                115.075(9)
_cell_angle_beta                 91.228(8)
_cell_angle_gamma                95.201(8)
_cell_formula_units_Z            2
_cell_length_a                   7.4264(7)
_cell_length_b                   11.9574(11)
_cell_length_c                   11.9660(9)
_cell_measurement_reflns_used    3110
_cell_measurement_temperature    99.9(6)
_cell_measurement_theta_max      75.2470
_cell_measurement_theta_min      4.3620
_cell_volume                     956.37(16)
_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      99.9(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2887
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -84.00  -6.00   1.00   12.50    --  -42.45 125.00  90.00   78
  2  \w   -119.00  -8.00   1.00   12.50    --  -42.45 -19.00   0.00  111
  3  \w   -114.00 -41.00   1.00   12.50    --  -42.45 -38.00 -60.00   73
  4  \w     25.00  50.00   1.00   12.50    --   42.45-125.00 -90.00   25
  5  \w     36.00  96.00   1.00   12.50    --   42.45-125.00   0.00   60
  6  \w     82.00 123.00   1.00   37.50    --  111.00  77.00 -30.00   41
  7  \w     64.00 111.00   1.00   37.50    --  111.00-111.00 -60.00   47
  8  \w     47.00 104.00   1.00   37.50    --  111.00 -94.00  90.00   57
  9  \w     84.00 122.00   1.00   37.50    --  111.00  61.00  60.00   38
 10  \w     43.00 137.00   1.00   37.50    --  111.00 -61.00 150.00   94
 11  \w     76.00 103.00   1.00   37.50    --  111.00-111.00  60.00   27
 12  \w     56.00 102.00   1.00   37.50    --  111.00 -94.00 150.00   46
 13  \w     44.00  71.00   1.00   37.50    --  111.00-111.00  60.00   27
 14  \w    127.00 177.00   1.00   37.50    --  111.00  77.00 -30.00   50
 15  \w     36.00 133.00   1.00   37.50    --  111.00 -30.00  30.00   97
 16  \w     37.00 130.00   1.00   37.50    --  111.00 -77.00 -60.00   93
 17  \w    137.00 164.00   1.00   37.50    --  111.00 111.00  90.00   27
 18  \w     45.00 137.00   1.00   37.50    --  111.00 -15.00-180.00   92
 19  \w     89.00 176.00   1.00   37.50    --  111.00  30.00  30.00   87
;
_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      0.0116791000
_diffrn_orient_matrix_UB_12      0.0654763000
_diffrn_orient_matrix_UB_13      -0.0865942000
_diffrn_orient_matrix_UB_21      -0.0297331000
_diffrn_orient_matrix_UB_22      0.1236541000
_diffrn_orient_matrix_UB_23      0.1090144000
_diffrn_orient_matrix_UB_31      0.2063030000
_diffrn_orient_matrix_UB_32      0.0300649000
_diffrn_orient_matrix_UB_33      0.0301780000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6147
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         4.088
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.697
_exptl_absorpt_correction_T_max  0.804
_exptl_absorpt_correction_T_min  0.295
_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    1.466
_exptl_crystal_description       needle
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.415
_exptl_crystal_size_mid          0.042
_exptl_crystal_size_min          0.028
_refine_diff_density_max         0.812
_refine_diff_density_min         -0.836
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3403
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0546
_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^)+(0.0891P)^2^+0.7585P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1486
_refine_ls_wR_factor_ref         0.1565
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2906
_reflns_number_total             3403
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc04248c2.cif
_cod_data_source_block           serc232-r1-rf
_cod_depositor_comments
'Adding full bibliography for 1565368--1565385.cif.'
_cod_database_code               1565374
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C15 O0.5 S1.5 Cl5 N2 H12'
_chemical_oxdiff_usercomment     ABS-326
_reflns_odcompleteness_completeness 99.79
_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:
 C15(H15A,H15B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C6(H6), C13(H13), C4(H4)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_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 1.742
_oxdiff_exptl_absorpt_empirical_full_min 0.521