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_1554320
_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         'C38 H28 N2 O3 S'
_chemical_formula_sum            'C38 H28 N2 O3 S'
_chemical_formula_weight         592.68
_chemical_name_systematic
((1R,2R,3R,3aS)-1'-benzyl-2'-oxo-1,2-dihydro-3aH-spiro[benzo[d]pyrrolo[2,1-b]thiazole-3,3'-indoline]-1,2-diyl)bis(phenylmethanone)
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-07-11
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-10-07 deposited with the CCDC.
2018-05-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.00774(12)
_cell_length_b                   11.44511(14)
_cell_length_c                   29.0288(3)
_cell_measurement_reflns_used    7029
_cell_measurement_temperature    293.8(5)
_cell_measurement_theta_max      72.4890
_cell_measurement_theta_min      4.9240
_cell_volume                     2992.71(6)
_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
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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_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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_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.8(5)
_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 0.986
_diffrn_measurement_details
;
  1 omega   20.00  104.00   1.0000    3.6900
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000  -30.0000 84

  2 omega   23.00   90.00   1.0000    3.6900
omega____ theta____ kappa____ phi______ frames
    -       36.5421 -125.0000   30.0000 67

  3 omega  -31.00   53.00   1.0000    3.6900
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -57.0000 -180.0000 84

  4 omega   10.00  104.00   1.0000    3.6900
omega____ theta____ kappa____ phi______ frames
    -       36.5421   77.0000 -150.0000 94

  5 omega    7.00  108.00   1.0000    3.6900
omega____ theta____ kappa____ phi______ frames
    -       36.5421   19.0000  -90.0000 101

  6 omega    1.00   75.00   1.0000    3.6900
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000 -120.0000 74

  7 omega   20.00  104.00   1.0000    3.6900
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000   60.0000 84

  8 omega   38.00   91.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 53

  9 omega   39.00  109.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 70

 10 omega   40.00   98.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 58

 11 omega   38.00   91.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 53

 12 omega   40.00   98.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  150.0000 58

 13 omega   38.00   91.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 53

 14 omega   39.00  109.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 70

 15 omega   39.00  177.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000   90.0000 138

 16 omega   20.00  104.00   1.0000    3.6900
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000  150.0000 84
;
_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1710428000
_diffrn_orient_matrix_UB_12      0.0025185000
_diffrn_orient_matrix_UB_13      0.0002224000
_diffrn_orient_matrix_UB_21      0.0015428000
_diffrn_orient_matrix_UB_22      0.0333831000
_diffrn_orient_matrix_UB_23      0.0514198000
_diffrn_orient_matrix_UB_31      0.0029756000
_diffrn_orient_matrix_UB_32      0.1303248000
_diffrn_orient_matrix_UB_33      -0.0131458000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            16569
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.684
_diffrn_reflns_theta_min         4.921
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.291
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85770
_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 light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_description       plate
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 2166 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.011(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         5811
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0487
_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^)+(0.0900P)^2^+0.3160P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1321
_refine_ls_wR_factor_ref         0.1365
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_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.970
_reflns_number_gt                5410
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_cod_data_source_file            c8qo00370j2.cif
_cod_data_source_block           fxm-zxy-spiro-1
_cod_database_code               1554320
_reflns_odcompleteness_completeness 99.74
_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
2.a Ternary CH refined with riding coordinates:
 C00C(H00C), C00F(H00F), C00Q(H00Q)
2.b Secondary CH2 refined with riding coordinates:
 C00M(H00a,H00b)
2.c Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00J(H00J), C00N(H00N), C00O(H00O), C00P(H00P), C00R(H00R),
 C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X),
 C00Y(H00Y), C00Z(H00Z), C010(H010), C011(H011), C012(H012), C013(H013),
 C014(H014), C015(H015), C016(H016), C017(H017), C018(H018)
;
_shelx_res_checksum              10364
_shelx_hkl_checksum              35463
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-07-06
_olex2_submission_special_instructions 'No special instructions were received'