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_1565373
_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      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
_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                103.868(4)
_cell_angle_beta                 94.530(5)
_cell_angle_gamma                95.061(4)
_cell_formula_units_Z            2
_cell_length_a                   8.9856(5)
_cell_length_b                   9.2182(3)
_cell_length_c                   9.3740(6)
_cell_measurement_reflns_used    5879
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      72.6660
_cell_measurement_theta_min      4.8830
_cell_volume                     746.85(7)
_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)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(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   -113.00 -13.00   0.50    0.50    --  -41.14 -57.00 120.00  200
  2  \w    -69.00  32.00   0.50    0.50    --  -41.14  57.00 -90.00  202
  3  \w     23.00  97.00   0.50    0.50    --   41.14-125.00 -30.00  148
  4  \w      9.00 117.00   0.50    0.50    --   41.14  77.00  30.00  216
  5  \w     28.00 115.00   0.50    0.76    --  104.67-111.00 150.00  174
  6  \w    100.00 178.00   0.50    0.76    --  104.67 111.00  60.00  156
  7  \w     29.00 137.00   0.50    0.76    --  104.67 -77.00 150.00  216
  8  \w     28.00 133.00   0.50    0.76    --  104.67 -30.00 -90.00  210
  9  \w     72.00 178.00   0.50    0.76    --  104.67  77.00-150.00  212
 10  \w     22.00 108.00   0.50    0.76    --  104.67 -94.00  60.00  172
 11  \w     22.00 108.00   0.50    0.76    --  104.67 -94.00 -90.00  172
 12  \w     32.00 131.00   0.50    0.76    --  104.67 -45.00 150.00  198
 13  \w     22.00 108.00   0.50    0.76    --  104.67 -94.00   0.00  172
 14  \w     32.00 131.00   0.50    0.76    --  104.67 -45.00-180.00  198
 15  \w     23.00 157.00   0.50    0.76    --  104.67 -15.00  30.00  268
 16  \w   -113.00 -13.00   0.50    0.50    --  -41.14 -57.00-120.00  200
 17  \w    -33.00  66.00   0.50    0.50    --   41.14 -38.00 -30.00  198
 18  \w      9.00 117.00   0.50    0.50    --   41.14  77.00 -60.00  216
 19  \w    -33.00  66.00   0.50    0.50    --   41.14 -38.00  90.00  198
;
_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      -0.1246967000
_diffrn_orient_matrix_UB_12      -0.0338747000
_diffrn_orient_matrix_UB_13      0.0949063000
_diffrn_orient_matrix_UB_21      -0.0018905000
_diffrn_orient_matrix_UB_22      0.1697901000
_diffrn_orient_matrix_UB_23      0.0656508000
_diffrn_orient_matrix_UB_31      -0.1199724000
_diffrn_orient_matrix_UB_32      0.0048733000
_diffrn_orient_matrix_UB_33      -0.1250943000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_unetI/netI     0.0186
_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       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7792
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        65.382
_diffrn_reflns_theta_max         65.382
_diffrn_reflns_theta_min         4.886
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    8.456
_exptl_absorpt_correction_T_max  0.507
_exptl_absorpt_correction_T_min  0.285
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
'CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)'
_exptl_crystal_colour            'clear orangish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.681
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_recrystallization_method
'Layering of dry hexane onto a saturated solution of the product in thionyl chloride.'
_exptl_crystal_size_max          0.239
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.119
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2562
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0275
_refine_ls_R_factor_gt           0.0267
_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^)+(0.0372P)^2^+0.4301P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0724
_refine_ls_wR_factor_ref         0.0730
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2470
_reflns_number_total             2562
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc04248c2.cif
_cod_data_source_block           serc010-r1-rf-fixed
_cod_depositor_comments
'Adding full bibliography for 1565368--1565385.cif.'
_cod_original_cell_volume        746.84(7)
_cod_database_code               1565373
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C14 H8 Cl4 N2 S1 '
_chemical_oxdiff_usercomment     ortho-methylphenylbenzamidine-SOCl2/hexane
_cell_oxdiff_angle_alpha         103.868(4)
_cell_oxdiff_angle_beta          94.530(5)
_cell_oxdiff_angle_gamma         95.061(4)
_cell_oxdiff_length_a            8.9856(5)
_cell_oxdiff_length_b            9.2182(3)
_cell_oxdiff_length_c            9.3740(6)
_cell_oxdiff_measurement_reflns_used 5879
_cell_oxdiff_volume              746.84(7)
_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, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C4(H4), C10(H10), C13(H13), C11(H11), C12(H12)
;
_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 1.395
_oxdiff_exptl_absorpt_empirical_full_min 0.811