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_1554323
_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         'C30 H22 Cl N O2 S'
_chemical_formula_sum            'C30 H22 Cl N O2 S'
_chemical_formula_weight         495.99
_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     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
;
2017-07-13 deposited with the CCDC.
2018-05-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.756(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4185(9)
_cell_length_b                   15.4927(12)
_cell_length_c                   15.8277(18)
_cell_measurement_reflns_used    2971
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.7250
_cell_measurement_theta_min      3.3910
_cell_volume                     2541.9(4)
_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    '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 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega  -32.00   12.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669   57.0000  -60.0000 44

  2 omega  -10.00   51.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669   77.0000  -60.0000 61

  3 omega  -21.00   15.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000  -30.0000 36

  4 omega  -84.00    4.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -38.0000  150.0000 88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0433188000
_diffrn_orient_matrix_UB_12      -0.0001859000
_diffrn_orient_matrix_UB_13      0.0375035000
_diffrn_orient_matrix_UB_21      0.0529559000
_diffrn_orient_matrix_UB_22      -0.0008096000
_diffrn_orient_matrix_UB_23      -0.0248769000
_diffrn_orient_matrix_UB_31      0.0010917000
_diffrn_orient_matrix_UB_32      0.0458092000
_diffrn_orient_matrix_UB_33      -0.0002907000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0587
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12090
_diffrn_reflns_point_group_measured_fraction_full 0.830
_diffrn_reflns_point_group_measured_fraction_max 0.813
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.088
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.260
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72632
_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    1.296
_exptl_crystal_description       block
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.737
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.083
_refine_ls_abs_structure_details
;
 Flack x determined using 1575 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     631
_refine_ls_number_reflns         8448
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.1377
_refine_ls_R_factor_gt           0.1004
_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^)+(0.1663P)^2^+3.3597P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2762
_refine_ls_wR_factor_ref         0.3105
_reflns_Friedel_coverage         0.571
_reflns_Friedel_fraction_full    0.651
_reflns_Friedel_fraction_max     0.615
_reflns_number_gt                5435
_reflns_number_total             8448
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00370j2.cif
_cod_data_source_block           170223_s2_zxy
_cod_depositor_comments
;

2022-05-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C30 H22 Cl N O2 S)'
_cod_original_formula_sum        'C60 H44 Cl2 N2 O4 S2'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     991.99
_cod_database_code               1554323
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c12h12n2o3s1cl1
_shelx_estimated_absorpt_t_max   0.914
_shelx_estimated_absorpt_t_min   0.903
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C12-C17
 1.37 with sigma of 0.01
 C16-C17
 1.37 with sigma of 0.01
 C16-C15
 1.37 with sigma of 0.01
 C15-C14
 1.37 with sigma of 0.01
 C13-C14
 1.37 with sigma of 0.01
 C12-C13
 1.37 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
 C1(H1), C8(H8), C9(H9), C10(H10), C31(H31), C38(H38), C39(H39), C40(H40)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C19(H19), C20(H20), C22(H22), C23(H23), C26(H26), C27(H27), C28(H28),
  C29(H29), C30(H30), C33(H33), C34(H34), C35(H35), C36(H36), C43(H43),
 C44(H44), C45(H45), C46(H46), C47(H47), C49(H49), C50(H50), C52(H52), C53(H53),
  C56(H56), C57(H57), C58(H58), C59(H59), C60(H60)
;
_olex2_submission_special_instructions 'No special instructions were received'