Synthesis of new hybrid 1,4-thiazinyl-1,2,3-dithiazolyl radicals via Smiles rearrangement
Vasko, Petra; Hurmalainen, Juha; Mansikkamäki, Akseli; Peuronen, Anssi; Mailman, Aaron; Tuononen, Heikki M.; Dalton Transactions  (2017) –; doi:10.1039/C7DT03243A

data_7044711
_publ_section_title
;
 Synthesis of new hybrid 1,4-thiazinyl-1,2,3-dithiazolyl radicals via
 Smiles rearrangement
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/C7DT03243A
_journal_year                    2017
_chemical_formula_moiety         'C12 H7 Cl N3 S3, C F3 O3 S'
_chemical_formula_sum            'C13 H7 Cl F3 N3 O3 S4'
_chemical_formula_weight         473.91
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-11-19
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_audit_update_record
;
2017-09-28 deposited with the CCDC.
2017-10-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.745(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4918(4)
_cell_length_b                   21.1396(9)
_cell_length_c                   11.7057(10)
_cell_measurement_reflns_used    2144
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      75.4420
_cell_measurement_theta_min      6.2490
_cell_volume                     1847.5(2)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  77.00   1.00   15.00    --   41.40 -99.00 120.00   76
  2  \w     15.00 113.00   1.00   15.00    --   41.40  57.00  60.00   98
  3  \w      3.00  63.00   1.00   15.00    --   41.40 -99.00-120.00   60
  4  \w     29.00 101.00   1.00   65.00    --  112.00 -94.00  60.00   72
  5  \w     99.00 160.00   1.00   65.00    --  112.00 125.00 120.00   61
  6  \w     40.00 140.00   1.00   65.00    --  112.00 -30.00  90.00  100
  7  \w     63.00  99.00   1.00   65.00    --  112.00 -94.00-120.00   36
  8  \w     83.00 167.00   1.00   65.00    --  112.00  61.00 -90.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1328811000
_diffrn_orient_matrix_UB_12      -0.0447300000
_diffrn_orient_matrix_UB_13      -0.0671518000
_diffrn_orient_matrix_UB_21      0.1163663000
_diffrn_orient_matrix_UB_22      0.0016082000
_diffrn_orient_matrix_UB_23      -0.1024366000
_diffrn_orient_matrix_UB_31      0.1067627000
_diffrn_orient_matrix_UB_32      -0.0574606000
_diffrn_orient_matrix_UB_33      0.0495126000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6154
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.989
_diffrn_reflns_theta_min         6.287
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.542
_exptl_absorpt_correction_T_max  0.936
_exptl_absorpt_correction_T_min  0.825
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.704
_exptl_crystal_description       plate
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.212
_exptl_crystal_size_mid          0.062
_exptl_crystal_size_min          0.061
_refine_diff_density_max         1.685
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.161
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.195
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3312
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.195
_refine_ls_R_factor_all          0.1117
_refine_ls_R_factor_gt           0.0989
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2731
_refine_ls_wR_factor_ref         0.2889
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2692
_reflns_number_total             3312
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7dt03243a3.cif
_cod_data_source_block           5b-OTf
_cod_database_code               7044711
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C13 H6 Cl N3 S4 O3 F3'
_chemical_oxdiff_usercomment     'ANR TBA-F 1:1 Ac-d6'
_reflns_odcompleteness_completeness 98.88
_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:
 C3(H3), C6(H6), C8(H8), C9(H9)
2.b Idealised Me refined as rotating group:
 C12(H12a,H12b,H12c)
;
_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 1.542
_oxdiff_exptl_absorpt_empirical_full_min 0.563