Enantioselective [3 + 2] cycloaddition and rearrangement of thiazolium salts to synthesize thiazole and 1,4-thiazine derivatives
Zhang, Xiying; Liu, Xiaohua; Zhang, Jianlin; Zhang, Dong; Lin, Lili; Feng, Xiaoming; Organic Chemistry Frontiers 5 (2018) 2126–; doi:10.1039/C8QO00370J

data_1554324
_publ_section_title
;
 Enantioselective [3 + 2] cycloaddition and rearrangement of thiazolium
 salts to synthesize thiazole and 1,4-thiazine derivatives
;
_journal_issue                   13
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2126
_journal_paper_doi               10.1039/C8QO00370J
_journal_volume                  5
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         '2(C F3 O3 S), C25 H48 Mg N4 O6, C4 H8 O2'
_chemical_formula_sum            'C31 H56 F6 Mg N4 O14 S2'
_chemical_formula_weight         911.22
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-12-20
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-12-22 deposited with the CCDC.
2018-05-28 downloaded from the CCDC.
;
_cell_angle_alpha                97.598(3)
_cell_angle_beta                 91.193(3)
_cell_angle_gamma                97.349(3)
_cell_formula_units_Z            1
_cell_length_a                   9.2007(2)
_cell_length_b                   9.2791(4)
_cell_length_c                   14.2370(5)
_cell_measurement_reflns_used    10018
_cell_measurement_temperature    139
_cell_measurement_theta_max      72.0910
_cell_measurement_theta_min      4.8510
_cell_volume                     1194.02(7)
_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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      139
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details
;
  1 omega  -45.00   -3.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       10.0000  127.0000  141.5279 42

  2 omega  -39.00   -6.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       18.0000  131.0000 -155.6515 33

  3 omega  -35.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -19.0000 -150.0000 101

  4 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000  -60.0000 74

  5 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000   60.0000 67

  6 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000   60.0000 84

  7 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000    0.0000 84

  8 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   38.0000 -120.0000 88

  9 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000 -120.0000 67

 10 omega  -33.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -38.0000  -60.0000 88

 11 omega    8.00   40.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.0000   83.0000 -177.5651 32

 12 omega    5.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.0000   89.0000   28.3164 28

 13 omega    6.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.0000   86.0000  -23.0508 29

 14 omega   14.00   46.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.0000   80.0000   98.7013 32

 15 omega   16.00   45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   82.0000  -99.6522 29

 16 omega   23.00   49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   78.0000   46.4366 26

 17 omega   25.00  117.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   74.0000  -86.0693 92

 18 omega   23.00   49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   78.0000  -16.1605 26

 19 omega   23.00   49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   78.0000 -139.2245 26

 20 omega   23.00  118.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   77.0000  174.3041 95

 21 omega   23.00   49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   78.0000  109.4089 26

 22 omega   28.00  121.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   75.0000   64.2131 93

 23 omega   32.00  125.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   76.0000  130.3532 93

 24 omega   31.00  126.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000  -60.5496 95

 25 omega   44.00  131.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   42.0000 -167.9255 87

 26 omega   40.00  129.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   69.0000  -13.6609 89

 27 omega   52.00  137.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   61.0000   77.4451 85

 28 omega   70.00  157.00   1.0000    3.8300
omega____ theta____ kappa____ phi______ frames
    -       90.0000   64.0000  -17.8398 87

 29 omega   81.00  176.00   1.0000    3.8300
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 95

 30 omega   90.00  175.00   1.0000    3.8300
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   60.0000 85

 31 omega   90.00  175.00   1.0000    3.8300
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -150.0000 85

 32 omega   90.00  175.00   1.0000    3.8300
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -60.0000 85

 33 omega   90.00  175.00   1.0000    3.8300
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   90.0000 85

 34 omega   90.00  175.00   1.0000    3.8300
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000    0.0000 85

 35 omega   81.00  176.00   1.0000    3.8300
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 95

 36 omega   90.00  175.00   1.0000    3.8300
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -90.0000 85

 37 omega   38.00  116.00   1.0000    3.8300
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 78

 38 omega   81.00  176.00   1.0000    3.8300
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 95

 39 omega   90.00  175.00   1.0000    3.8300
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -120.0000 85

 40 omega   41.00  126.00   1.0000    3.8300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  150.0000 85

 41 omega   81.00  176.00   1.0000    3.8300
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 95

 42 omega   81.00  176.00   1.0000    3.8300
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 95

 43 omega   81.00  176.00   1.0000    3.8300
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 95

 44 omega   40.00   98.00   1.0000    3.8300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 58

 45 omega  100.00  178.00   1.0000    3.8300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -150.0000 78

 46 omega   38.00  116.00   1.0000    3.8300
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  150.0000 78

 47 omega   81.00  176.00   1.0000    3.8300
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 95

 48 omega   81.00  176.00   1.0000    3.8300
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 95

 49 omega   90.00  131.00   1.0000    3.8300
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -180.0000 41

 50 omega   74.00  101.00   1.0000    3.8300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 27

 51 omega  122.00  176.00   1.0000    3.8300
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 54

 52 omega   90.00  123.00   1.0000    3.8300
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  120.0000 33

 53 omega  129.00  156.00   1.0000    3.8300
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  120.0000 27

 54 omega   81.00  108.00   1.0000    3.8300
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 27

 55 omega  122.00  174.00   1.0000    3.8300
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 52

 56 omega   82.00  116.00   1.0000    3.8300
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 34

 57 omega  139.00  170.00   1.0000    3.8300
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 31

 58 omega   81.00  108.00   1.0000    3.8300
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 27

 59 omega   82.00  107.00   1.0000    3.8300
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 25

 60 omega   55.00  111.00   1.0000    3.8300
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -30.0000 56

 61 omega   90.00  161.00   1.0000    3.8300
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  150.0000 71
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0354182000
_diffrn_orient_matrix_UB_12      0.0792048000
_diffrn_orient_matrix_UB_13      0.0972238000
_diffrn_orient_matrix_UB_21      0.1586535000
_diffrn_orient_matrix_UB_22      -0.0018950000
_diffrn_orient_matrix_UB_23      0.0361267000
_diffrn_orient_matrix_UB_31      0.0460326000
_diffrn_orient_matrix_UB_32      0.1492446000
_diffrn_orient_matrix_UB_33      -0.0343132000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0609
_diffrn_reflns_av_unetI/netI     0.0569
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            24144
_diffrn_reflns_point_group_measured_fraction_full 0.909
_diffrn_reflns_point_group_measured_fraction_max 0.886
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.827
_diffrn_reflns_theta_min         4.850
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.868
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.14044
_exptl_absorpt_correction_type   multi-scan
_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)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 3083 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     535
_refine_ls_number_reflns         8450
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0610
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1344P)^2^+0.0891P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1662
_refine_ls_wR_factor_ref         0.1745
_reflns_Friedel_coverage         0.806
_reflns_Friedel_fraction_full    0.819
_reflns_Friedel_fraction_max     0.790
_reflns_number_gt                7886
_reflns_number_total             8450
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00370j2.cif
_cod_data_source_block           fxm-zxy-2-139k_sq
_cod_original_cell_volume        1194.03(7)
_cod_database_code               1554324
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.706
_shelx_estimated_absorpt_t_min   0.487
_reflns_odcompleteness_completeness 99.91
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O005-H00B
 0.85 with sigma of 0.02
 O00B-H00D
 0.85 with sigma of 0.02
3.a Rotating group:
 O005(H00A), O00B(H00C)
3.b Ternary CH refined with riding coordinates:
 C00T(H00T), C00Z(H00Z), C013(H013), C01H(H01W)
3.c Secondary CH2 refined with riding coordinates:
 C00V(H00E,H00F), C00W(H00G,H00H), C00Y(H00I,H00J), C010(H01A,H01B), C012(H01C,
 H01D), C015(H01E,H01F), C016(H01G,H01H), C017(H2AA,H), C018(H01I,H01J),
 C019(H01K,H01L), C01A(H01M,H01N), C01C(H01O,H01P), C01D(H01Q,H01R), C01E(H01S,
 H01T), C01F(H01U,H01V), C01J(H01X,H01Y), C01N(H01Z,HC), C01O(H01,HD),
 C01Q(H0AA,HG), C01R(H1AA,HH)
3.d Aromatic/amide H refined with riding coordinates:
 N00M(H00M), N00R(H00R)
3.e Idealised Me refined as rotating group:
 C01K(H3AA,HA,HB), C01P(H4AA,HE,HF)
;
_olex2_submission_special_instructions 'No special instructions were received'