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_1554322
_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         'C26 H21 N O4 S'
_chemical_formula_sum            'C26 H21 N O4 S'
_chemical_formula_weight         443.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-07-13
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-07-13 deposited with the CCDC.
2018-05-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.301(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.34670(18)
_cell_length_b                   16.1435(4)
_cell_length_c                   10.7987(3)
_cell_measurement_reflns_used    3151
_cell_measurement_temperature    295.97(11)
_cell_measurement_theta_max      72.5350
_cell_measurement_theta_min      4.9450
_cell_volume                     1099.73(5)
_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
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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)'
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_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.97(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details
;
  1 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000 -180.0000 67

  2 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000  120.0000 84

  3 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000 -150.0000 74

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

  5 omega  -35.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -19.0000  -90.0000 101

  6 omega   70.00  178.00   1.0000    1.9500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -60.0000 108

  7 omega   38.00   91.00   1.0000    1.9500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 53

  8 omega   39.00  109.00   1.0000    1.9500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 70

  9 omega  100.00  178.00   1.0000    1.9500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -150.0000 78

 10 omega   40.00   98.00   1.0000    1.9500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 58

 11 omega   38.00   91.00   1.0000    1.9500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 53

 12 omega   40.00   98.00   1.0000    1.9500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  150.0000 58

 13 omega   39.00  109.00   1.0000    1.9500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  120.0000 70

 14 omega   38.00   91.00   1.0000    1.9500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 53

 15 omega   87.00  178.00   1.0000    1.9500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   30.0000 91

 16 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000   30.0000 84

 17 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000  -90.0000 94
;
_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      0.1682003000
_diffrn_orient_matrix_UB_12      -0.0072282000
_diffrn_orient_matrix_UB_13      0.1136866000
_diffrn_orient_matrix_UB_21      -0.1485104000
_diffrn_orient_matrix_UB_22      -0.0574270000
_diffrn_orient_matrix_UB_23      0.0642754000
_diffrn_orient_matrix_UB_31      0.0963091000
_diffrn_orient_matrix_UB_32      -0.0758853000
_diffrn_orient_matrix_UB_33      -0.0595423000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6601
_diffrn_reflns_point_group_measured_fraction_full 0.840
_diffrn_reflns_point_group_measured_fraction_max 0.812
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.559
_diffrn_reflns_theta_min         4.948
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.584
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53292
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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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 yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.531
_refine_diff_density_rms         0.091
_refine_ls_abs_structure_details
;
 Flack x determined using 1154 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.022(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         3544
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0618
_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^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1519
_refine_ls_wR_factor_ref         0.1572
_reflns_Friedel_coverage         0.594
_reflns_Friedel_fraction_full    0.669
_reflns_Friedel_fraction_max     0.628
_reflns_number_gt                3371
_reflns_number_total             3544
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00370j2.cif
_cod_data_source_block           fxm-6
_cod_database_code               1554322
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.90
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C007(H007), C00H(H00H)
2.b Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00E(H00E), C00G(H00G), C00J(H00J), C00L(H00L), C00M(H00M),
 C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S),
 C00T(H00T), C00U(H00U), C00W(H00W)
2.c Idealised Me refined as rotating group:
 C00V(H00B,H00C,H00D)
2.d Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
_olex2_date_sample_data_collection 2017-04-25
_olex2_submission_special_instructions 'No special instructions were received'