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_1554321
_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 rmad
_chemical_formula_moiety         'C38 H28 N2 O4 S'
_chemical_formula_sum            'C38 H28 N2 O4 S'
_chemical_formula_weight         608.68
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
;
2017-11-29 deposited with the CCDC.
2018-05-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.279(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.8962(11)
_cell_length_b                   11.3205(8)
_cell_length_c                   20.153(2)
_cell_measurement_reflns_used    2450
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.0690
_cell_measurement_theta_min      3.7130
_cell_volume                     3320.7(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
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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)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details
;
  1 omega   32.00   57.60   0.8000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669 -178.0000   60.0000 32

  2 omega   12.00   52.00   0.8000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669   57.0000   60.0000 50

  3 omega  -78.00   10.00   0.8000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -19.0000  150.0000 110

  4 omega  -80.00    0.00   0.8000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -57.0000  -90.0000 100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0319498000
_diffrn_orient_matrix_UB_12      0.0060922000
_diffrn_orient_matrix_UB_13      -0.0313602000
_diffrn_orient_matrix_UB_21      -0.0356431000
_diffrn_orient_matrix_UB_22      -0.0207765000
_diffrn_orient_matrix_UB_23      0.0154247000
_diffrn_orient_matrix_UB_31      -0.0092058000
_diffrn_orient_matrix_UB_32      0.0587686000
_diffrn_orient_matrix_UB_33      0.0087117000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8439
_diffrn_reflns_point_group_measured_fraction_full 0.729
_diffrn_reflns_point_group_measured_fraction_max 0.707
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.500
_diffrn_reflns_theta_min         3.107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83304
_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    1.218
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 1012 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         4866
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0441
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0640P)^2^+0.0320P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1095
_refine_ls_wR_factor_ref         0.1153
_reflns_Friedel_coverage         0.392
_reflns_Friedel_fraction_full    0.457
_reflns_Friedel_fraction_max     0.420
_reflns_number_gt                3997
_reflns_number_total             4866
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00370j2.cif
_cod_data_source_block           170223_s1_zxy
_cod_original_cell_volume        3320.6(5)
_cod_database_code               1554321
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         c12h12n2o3s1
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.946
_reflns_odcompleteness_completeness 96.90
_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 C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C009(H009), C00L(H00L), C00P(H00P)
2.b Secondary CH2 refined with riding coordinates:
 C012(H01A,H01B)
2.c Aromatic/amide H refined with riding coordinates:
 C00F(H00F), C00G(H00G), C00I(H00I), C00M(H00M), C00N(H00N), C00O(H00O),
 C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T), C00V(H00V), C00W(H00W),
 C00X(H00X), C00Y(H00Y), C00Z(H00Z), C010(H010), C011(H011), C013(H013),
 C015(H015), C1(H1), C2(H2), C3(H3), C0AA(H0AA)
;
_shelx_res_checksum              7521
_shelx_hkl_checksum              57182
_olex2_submission_special_instructions 'No special instructions were received'