Highly diastereo- and enantioselective Michael addition of 3-substituted benzofuran-2(3H)-ones to 4-oxo-enoates catalyzed by lanthanide(III) complexes
Zhen Wang; Qian Yao; Tengfei Kang; Juhua Feng; Xiaohua Liu; Lili Lin; Xiaoming Feng; Chem.Commun. 50 (2014) 4918–; doi:10.1039/C4CC01499E

data_7112617
_publ_section_title
;
 Highly diastereo- and enantioselective Michael addition of 3-substituted
 benzofuran-2(3H)-ones to 4-oxo-enoates catalyzed by lanthanide(III)
 complexes
;
_journal_name_full               Chem.Commun.
_journal_page_first              4918
_journal_paper_doi               10.1039/C4CC01499E
_journal_volume                  50
_journal_year                    2014
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C25 H22 O5 S'
_chemical_formula_sum            'C25 H22 O5 S'
_chemical_formula_weight         434.48
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2013-09-10
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.370(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.7042(4)
_cell_length_b                   15.7653(7)
_cell_length_c                   9.1879(4)
_cell_measurement_reflns_used    1506
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.0022
_cell_measurement_theta_min      3.0138
_cell_volume                     1081.04(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL-2012, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -73.00  -39.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      -17.5174 -178.0000  -30.0000 34

  2 omega  -22.00    5.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      -17.5174  -99.0000  -30.0000 27

  3 omega  -36.00   54.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      -17.5174   38.0000  -30.0000 90

  4 omega   37.00   89.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -       19.3143   77.0000 -150.0000 52

  5 omega  -49.00  -24.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -       19.3143  -57.0000 -180.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0460970000
_diffrn_orient_matrix_UB_12      0.0257578000
_diffrn_orient_matrix_UB_13      -0.0414321000
_diffrn_orient_matrix_UB_21      0.0672093000
_diffrn_orient_matrix_UB_22      -0.0315624000
_diffrn_orient_matrix_UB_23      0.0071575000
_diffrn_orient_matrix_UB_31      -0.0488852000
_diffrn_orient_matrix_UB_32      -0.0191076000
_diffrn_orient_matrix_UB_33      -0.0676932000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0562
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4739
_diffrn_reflns_point_group_measured_fraction_full 0.791
_diffrn_reflns_point_group_measured_fraction_max 0.776
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.365
_diffrn_reflns_theta_min         3.020
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 755 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.13(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3432
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0548
_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^)+(0.0683P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1238
_refine_ls_wR_factor_ref         0.1396
_reflns_Friedel_coverage         0.498
_reflns_Friedel_fraction_full    0.567
_reflns_Friedel_fraction_max     0.536
_reflns_number_gt                2655
_reflns_number_total             3432
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc01499e2.cif
_cod_data_source_block           130909_s1_wz
_cod_original_cell_volume        1081.03(9)
_cod_database_code               7112617
_chemical_oxdiff_formula         C25H22O5S1
_reflns_odcompleteness_completeness 99.78
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C23(H23)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C12(H12), C13(H13), C14(H14), C15(H15), C17(H17),
 C18(H18), C19(H19), C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C25(H25A,H25B,H25C)
;
_shelx_estimated_absorpt_t_max   0.964
_shelx_estimated_absorpt_t_min   0.947
_shelx_hkl_checksum              60717
_shelx_res_checksum              53636
_shelxl_version_number           2013-2