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_1565377
_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 H10 Cl3 N2 S'
_chemical_formula_sum            'C15 H10 Cl3 N2 S'
_chemical_formula_weight         376.66
_chemical_properties_physical    Air-sensitive,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             2018-06-28
_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                91.036(3)
_cell_angle_beta                 107.068(4)
_cell_angle_gamma                109.355(3)
_cell_formula_units_Z            4
_cell_length_a                   9.9369(4)
_cell_length_b                   12.2664(4)
_cell_length_c                   13.3652(5)
_cell_measurement_reflns_used    14186
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.1990
_cell_measurement_theta_min      3.8030
_cell_volume                     1457.25(11)
_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    5.00    --  -40.39 -38.00  30.00   99
  2  \w   -120.00   1.00   1.00    5.00    --  -40.39 -19.00  90.00  121
  3  \w    -95.00  -2.00   1.00    5.00    --  -40.39 125.00-180.00   93
  4  \w      4.00  33.00   1.00    5.00    --   40.39  89.00  55.03   29
  5  \w     23.00  96.00   1.00    5.00    --   40.39-125.00   0.00   73
  6  \w     23.00  96.00   1.00    5.00    --   40.39-125.00-180.00   73
  7  \w     16.00 115.00   1.00    5.00    --   40.39  38.00 -30.00   99
  8  \w     36.00 116.00   1.00   17.50    --  112.00-111.00  30.00   80
  9  \w     40.00 141.00   1.00   17.50    --  112.00 -61.00  30.00  101
 10  \w     39.00 138.00   1.00   17.50    --  112.00 -45.00 166.81   99
 11  \w     36.00 116.00   1.00   17.50    --  112.00-111.00  60.00   80
 12  \w     57.00 151.00   1.00   17.50    --  112.00 178.00   0.00   94
 13  \w     57.00 151.00   1.00   17.50    --  112.00 178.00  90.00   94
 14  \w    100.00 178.00   1.00   17.50    --  112.00 111.00   0.00   78
 15  \w     36.00 116.00   1.00   17.50    --  112.00-111.00 -30.00   80
 16  \w     36.00 116.00   1.00   17.50    --  112.00-111.00-150.00   80
 17  \w     83.00 178.00   1.00   17.50    --  112.00  61.00-180.00   95
 18  \w     29.00 109.00   1.00   17.50    --  112.00 -94.00  30.00   80
 19  \w     36.00 116.00   1.00   17.50    --  112.00-111.00 -90.00   80
 20  \w     57.00 151.00   1.00   17.50    --  112.00 178.00 150.00   94
 21  \w     36.00 116.00   1.00   17.50    --  112.00-111.00-180.00   80
 22  \w     29.00 109.00   1.00   17.50    --  112.00 -94.00  60.00   80
 23  \w     57.00 151.00   1.00   17.50    --  112.00 178.00 -30.00   94
 24  \w     86.00 178.00   1.00   17.50    --  112.00  45.00 150.00   92
 25  \w     57.00 151.00   1.00   17.50    --  112.00 178.00  30.00   94
 26  \w     79.00 178.00   1.00   17.50    --  112.00  77.00-150.00   99
 27  \w     79.00 178.00   1.00   17.50    --  112.00  77.00  90.00   99
 28  \w     40.00 141.00   1.00   17.50    --  112.00 -61.00  90.00  101
 29  \w     83.00 178.00   1.00   17.50    --  112.00  61.00 120.00   95
 30  \w     83.00 178.00   1.00   17.50    --  112.00  61.00  60.00   95
 31  \w     84.00 178.00   1.00   17.50    --  112.00  30.00-180.00   94
 32  \w     26.00 178.00   1.00   17.50    --  112.00   5.00 -57.00  152
 33  \w     29.00 109.00   1.00   17.50    --  112.00 -94.00 120.00   80
 34  \w     29.00 109.00   1.00   17.50    --  112.00 -94.00  90.00   80
 35  \w     86.00 178.00   1.00   17.50    --  112.00  45.00 -60.00   92
 36  \w     39.00 138.00   1.00   17.50    --  112.00 -45.00-180.00   99
 37  \w     40.00 141.00   1.00   17.50    --  112.00 -61.00-150.00  101
 38  \w     36.00 145.00   1.00   17.50    --  112.00 -77.00-180.00  109
 39  \w     81.00 140.00   1.00   17.50    --  112.00 -26.00-169.80   59
;
_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      0.1510701000
_diffrn_orient_matrix_UB_12      0.0924662000
_diffrn_orient_matrix_UB_13      0.0032386000
_diffrn_orient_matrix_UB_21      -0.0645135000
_diffrn_orient_matrix_UB_22      0.0064988000
_diffrn_orient_matrix_UB_23      -0.1186400000
_diffrn_orient_matrix_UB_31      -0.0551742000
_diffrn_orient_matrix_UB_32      0.0970678000
_diffrn_orient_matrix_UB_33      0.0263586000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            29597
_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         71.061
_diffrn_reflns_theta_min         3.488
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.970
_exptl_absorpt_correction_T_max  0.759
_exptl_absorpt_correction_T_min  0.256
_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 violet'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_description       rhombohedral
_exptl_crystal_F_000             724
_exptl_crystal_size_max          0.273
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.048
_refine_diff_density_max         2.233
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.160
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         5631
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0679
_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^)+(0.1130P)^2^+3.1661P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1871
_refine_ls_wR_factor_ref         0.1907
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5213
_reflns_number_total             5631
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc04248c2.cif
_cod_data_source_block           serc079-r1-rf
_cod_depositor_comments
;
Adding full bibliography for 1565368--1565385.cif.

2022-04-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C30 H20 Cl6 N4 S2'
_cod_original_formula_weight         713.32
_cod_original_formula_moiety         '2(C15 H10 Cl3 N2 S)'
_cod_original_formula_units_Z            2
_cod_original_cell_volume        1457.25(10)
_cod_database_code               1565377
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'N4 S4 Cl6 C30 H20'
_chemical_oxdiff_usercomment     3,5-dimethyl-S-Radical
_shelx_estimated_absorpt_t_max   0.731
_shelx_estimated_absorpt_t_min   0.252
_reflns_odcompleteness_completeness 100.00
_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:
 C14(H14A,H14B), C29(H29A,H29B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C22(H22), C18(H18), C5(H5), C4(H4), C21(H21), C6(H6),
 C20(H20), C19(H19)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C30(H30A,H30B,H30C)
;
_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 1.653
_oxdiff_exptl_absorpt_empirical_full_min 0.496