Diastereo- and enantioselective direct vinylogous Michael addition of gamma-substituted butenolides to 2-enoylpyridines catalyzed by chiral bifunctional amine-squaramides
Zhen-Hua Wang; Zhi-Jun Wu; Xue-Qun Huang; Deng-Feng Yue; Yong You; Xiao-Ying Xu; Xiao-Mei Zhang; Wei-Cheng Yuan; Chem.Commun. 51 (2015) 15835–; doi:10.1039/C5cc06383C

data_7117992
_publ_section_title
;
 Diastereo- and enantioselective direct vinylogous Michael addition of
 gamma-substituted butenolides to 2-enoylpyridines catalyzed by chiral
 bifunctional amine-squaramides
;
_journal_name_full               Chem.Commun.
_journal_page_first              15835
_journal_paper_doi               10.1039/C5cc06383C
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C22 H17 N O3 S'
_chemical_formula_weight         375.30
_chemical_name_systematic
;
 ?
;
_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'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-03-31 deposited with the CCDC.
2015-09-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.466(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.9821(9)
_cell_length_b                   6.4380(3)
_cell_length_c                   15.2420(5)
_cell_measurement_reflns_used    7000
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      69.1640
_cell_measurement_theta_min      4.5270
_cell_volume                     1916.11(14)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-2013
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      290(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_laue_measured_fraction_full 0.995
_diffrn_reflns_laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12444
_diffrn_reflns_point_group_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.700
_diffrn_reflns_theta_min         4.529
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.679
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.17818
_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            colorless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.310
_refine_diff_density_max         0.991
_refine_diff_density_min         -0.546
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.066(58)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3429
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0802
_refine_ls_R_factor_gt           0.0788
_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^)+(0.1595P)^2^+1.3887P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2317
_refine_ls_wR_factor_ref         0.2342
_reflns_Friedel_coverage         0.743
_reflns_friedel_fraction_full    0.909
_reflns_friedel_fraction_max     0.890
_reflns_number_gt                3320
_reflns_number_total             3429
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc06383c2.cif
_cod_data_source_block           shelxl
_cod_database_code               7117992
_shelx_estimated_absorpt_t_min   0.560
_shelx_estimated_absorpt_t_max   0.624
_shelxl_version_number           2013-4
_shelx_res_checksum              69378