Diastereoselective and Enantioselective Alleno-aldol Reaction of Allenoates with Isatins to Synthesis of Carbinol Allenoates Catalyzed by Gold
Wang, Gang; Liu, Xiaohua; Chen, Yushuang; Yang, Jian; Li, Jun; Lin, Lili; Feng, Xiaoming; ACS Catalysis 6 (2016) 2482–; doi:10.1021/acscatal.6b00294

data_4513839
_publ_section_title
;
 Diastereoselective and Enantioselective Alleno-aldol Reaction of
 Allenoates with Isatins to Synthesis of Carbinol Allenoates Catalyzed by
 Gold
;
_journal_issue                   4
_journal_name_full               'ACS Catalysis'
_journal_page_first              2482
_journal_paper_doi               10.1021/acscatal.6b00294
_journal_volume                  6
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H19 N O4'
_chemical_formula_sum            'C21 H19 N O4'
_chemical_formula_weight         349.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-06-23
_audit_creation_method
;
Olex2 1.2
(compiled 2014.06.18 svn.r2945 for OlexSys, GUI svn.r4846)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.32516(19)
_cell_length_b                   13.4286(3)
_cell_length_c                   19.6168(6)
_cell_measurement_reflns_used    5457
_cell_measurement_temperature    119.99(10)
_cell_measurement_theta_max      72.6320
_cell_measurement_theta_min      5.5760
_cell_volume                     1929.64(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      119.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000    0.0000 84

  2 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000  -90.0000 67

  3 omega  -31.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -77.0000  -30.0000 94

  4 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000  -90.0000 74

  5 omega    7.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   19.0000 -150.0000 101

  6 omega   39.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   60.0000 70

  7 omega   39.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -60.0000 70

  8 omega   38.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 53

  9 omega   90.00  175.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -180.0000 85

 10 omega   38.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 53

 11 omega   41.00  126.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  120.0000 85

 12 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000  -30.0000 94

 13 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000  -90.0000 84

 14 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000  120.0000 84

 15 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   38.0000   90.0000 88

 16 omega   39.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000    0.0000 59
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0194731000
_diffrn_orient_matrix_UB_12      0.0517432000
_diffrn_orient_matrix_UB_13      0.0696879000
_diffrn_orient_matrix_UB_21      0.0402557000
_diffrn_orient_matrix_UB_22      -0.0994101000
_diffrn_orient_matrix_UB_23      0.0361448000
_diffrn_orient_matrix_UB_31      0.2056419000
_diffrn_orient_matrix_UB_32      0.0243697000
_diffrn_orient_matrix_UB_33      -0.0004488000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10511
_diffrn_reflns_point_group_measured_fraction_full 0.920
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.077
_diffrn_reflns_theta_min         4.508
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.682
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_description
;
;
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 1112 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3212
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0453
_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^)+(0.0900P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1215
_reflns_Friedel_coverage         0.605
_reflns_Friedel_fraction_full    0.823
_reflns_Friedel_fraction_max     0.831
_reflns_number_gt                3049
_reflns_number_total             3212
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs6b00294_si_002.cif
_cod_data_source_block           fxm-wg-x-6-120k
_cod_depositor_comments          'Adding full bibliography for 4513839.cif.'
_cod_database_code               4513839
_shelxl_version_number           2014-1
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H2(0.038) H1(0.03) H3(0.036) H9(0.027) H18(0.038) H14(0.036)
 H1A(0.039) H2A(0.038) H16(0.043) H5(0.034) H17(0.044) H12A(0.036) H12B(0.036)
 H15(0.041) H20A(0.048) H20B(0.048) H21A(0.087) H21B(0.087) H21C(0.087)
 Fixed X: H2(-0.4907) H1(0.1145) H3(0.2554) H9(-0.2531) H18(-1.0521) H14(-
 0.5646) H1A(-0.1164) H2A(0.175) H16(-0.9023) H5(-0.3386) H17(-1.1155) H12A(-
 0.8715) H12B(-0.6756) H15(-0.6276) H20A(-0.9177) H20B(-0.8561) H21A(-0.5879)
 H21B(-0.6497) H21C(-0.7574)
 Fixed Y: H2(-0.7333) H1(-0.7404) H3(-0.7078) H9(-0.5129) H18(-0.4452) H14(-
 0.3514) H1A(-0.5994) H2A(-0.653) H16(-0.1623) H5(-0.5994) H17(-0.2881) H12A(-
 0.5574) H12B(-0.5519) H15(-0.1937) H20A(-0.4508) H20B(-0.3424) H21A(-0.363)
 H21B(-0.4707) H21C(-0.378)
 Fixed Z: H2(-0.4239) H1(-0.4331) H3(-0.3068) H9(-0.4293) H18(-0.5888) H14(-
 0.5249) H1A(-0.1749) H2A(-0.1977) H16(-0.62) H5(-0.2597) H17(-0.6311) H12A(-
 0.5229) H12B(-0.555) H15(-0.5663) H20A(-0.2781) H20B(-0.2985) H21A(-0.236)
 H21B(-0.2155) H21C(-0.1883)
;
_shelx_res_checksum              73606
_shelx_hkl_checksum              64910
_olex2_submission_special_instructions 'No special instructions were received'