Asymmetric [4 + 2] annulation of 5H-thiazol-4-ones with a chiral dipeptide-based Brønsted base catalyst
Zhu, Bo; Qiu, Shuai; Li, Jiangtao; Coote, Michelle L.; Lee, Richmond; Jiang, Zhiyong; Chem. Sci. 7 (2016) 6060–; doi:10.1039/C6SC02039A

data_1543433
_publ_section_title
;
 Asymmetric [4 + 2] annulation of 5H-thiazol-4-ones with a chiral
 dipeptide-based Br\/onsted base catalyst
;
_journal_issue                   9
_journal_name_full               'Chem. Sci.'
_journal_page_first              6060
_journal_paper_doi               10.1039/C6SC02039A
_journal_volume                  7
_journal_year                    2016
_chemical_formula_sum            'C25 H19 F3 N2 O3 S'
_chemical_formula_weight         484.48
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-08-19 deposited with the CCDC.
2016-06-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.949(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.2983(4)
_cell_length_b                   40.617(2)
_cell_length_c                   11.3731(4)
_cell_measurement_temperature    291(2)
_cell_volume                     4806.1(4)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       48
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            19277
_diffrn_reflns_point_group_measured_fraction_full 0.732
_diffrn_reflns_point_group_measured_fraction_max 0.732
_diffrn_reflns_theta_full        67.078
_diffrn_reflns_theta_max         67.078
_diffrn_reflns_theta_min         4.221
_exptl_absorpt_coefficient_mu    1.662
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_F_000             2000
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.536
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Flack x determined using 2364 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.032(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1233
_refine_ls_number_reflns         12573
_refine_ls_number_restraints     102
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_gt           0.0784
_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^)+(0.1102P)^2^+3.3396P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2049
_refine_ls_wR_factor_ref         0.2157
_reflns_Friedel_coverage         0.443
_reflns_Friedel_fraction_full    0.456
_reflns_Friedel_fraction_max     0.456
_reflns_number_gt                10148
_reflns_number_total             12573
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6sc02039a2.cif
_cod_data_source_block           zb33047
_cod_depositor_comments
'Adding full bibliography for 1543432--1543434.cif.'
_cod_original_cell_volume        4806.0(4)
_cod_database_code               1543433
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.732
_shelx_estimated_absorpt_t_max   0.937
_shelx_res_checksum              59747