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_7044708
_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         'C10 H12 N5 S, C F3 O3 S, C2 H3 N'
_chemical_formula_sum            'C13 H15 F3 N6 O3 S2'
_chemical_formula_weight         424.43
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-11-29
_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                86.713(6)
_cell_angle_beta                 78.198(6)
_cell_angle_gamma                89.864(6)
_cell_formula_units_Z            2
_cell_length_a                   6.2134(4)
_cell_length_b                   10.3216(7)
_cell_length_c                   14.0396(9)
_cell_measurement_reflns_used    3077
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      28.8200
_cell_measurement_theta_min      3.8630
_cell_volume                     879.87(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0107
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega  -42.00   47.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.1368   77.0000   60.0000 89

  2 omega  -53.00   42.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2305  -37.0000  150.0000 95

  3 omega  -86.00   12.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.1368  -77.0000  -60.0000 98

  4 omega   22.00   61.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2305  -99.0000 -150.0000 39
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0245301000
_diffrn_orient_matrix_UB_12      0.0060377000
_diffrn_orient_matrix_UB_13      0.0511486000
_diffrn_orient_matrix_UB_21      -0.1041110000
_diffrn_orient_matrix_UB_22      0.0261434000
_diffrn_orient_matrix_UB_23      -0.0032301000
_diffrn_orient_matrix_UB_31      -0.0464855000
_diffrn_orient_matrix_UB_32      -0.0633919000
_diffrn_orient_matrix_UB_33      0.0067998000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5350
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_min         2.969
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.362
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.934
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_description       plank
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.2595
_exptl_crystal_size_mid          0.2133
_exptl_crystal_size_min          0.0385
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3444
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0366
_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^)+(0.0380P)^2^+0.3182P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.0950
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2998
_reflns_number_total             3444
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7dt03243a3.cif
_cod_data_source_block           3c-OTf
_cod_original_cell_volume        879.87(11)
_cod_database_code               7044708
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         C11H12F3O3N5S2
_reflns_odcompleteness_completeness 99.26
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C8(H8), C9(H9)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C13(H13A,H13B,H13C)
;
_olex2_submission_special_instructions 'No special instructions were received'