Diastereodivergent asymmetric Michael-alkylation reactions using chiral <i>N</i>,<i>N</i>'-dioxide/metal complexes.
Kuang, Yulong; Shen, Bin; Dai, Li; Yao, Qian; Liu, Xiaohua; Lin, Lili; Feng, Xiaoming; Chemical science 9 (2018) 688–692; doi:10.1039/c7sc02757e

data_1547942
_publ_section_title
;
 Diastereodivergent asymmetric Michael-alkylation reactions using chiral
 <i>N</i>,<i>N</i>'-dioxide/metal complexes.
;
_journal_issue                   3
_journal_name_full               'Chemical science'
_journal_page_first              688
_journal_page_last               692
_journal_paper_doi               10.1039/c7sc02757e
_journal_volume                  9
_journal_year                    2018
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C24 H23 N O6'
_chemical_formula_sum            'C24 H23 N O6'
_chemical_formula_weight         421.43
_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             2015-01-26
_audit_creation_method
;
Olex2 1.2
(compiled 2014.05.21 svn.r2940 for OlexSys, GUI svn.r4846)
;
_audit_update_record
;
2015-07-09 deposited with the CCDC.
2017-11-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.3470(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.51320(10)
_cell_length_b                   9.68370(10)
_cell_length_c                   10.80560(10)
_cell_measurement_reflns_used    12537
_cell_measurement_temperature    293
_cell_measurement_theta_max      72.6950
_cell_measurement_theta_min      4.5730
_cell_volume                     1098.206(19)
_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    'ShelXT (Sheldrick, 2008)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
  1 omega  -18.00   71.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        2.0000   36.0000  126.8295 89

  2 omega  -38.00   -6.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       18.0000  130.0000  -44.3546 32

  3 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000   60.0000 84

  4 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000  -60.0000 74

  5 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000  -30.0000 84

  6 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   38.0000 -120.0000 88

  7 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   38.0000  -30.0000 88

  8 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000 -150.0000 74

  9 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000  -90.0000 84

 10 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000  150.0000 67

 11 omega    4.00   32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.0000   90.0000  136.5377 28

 12 omega    7.00   36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.0000   85.0000  118.0698 29

 13 omega    5.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.0000   88.0000    9.6228 28

 14 omega   11.00   38.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.0000   84.0000   46.5190 27

 15 omega   12.00   40.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.0000   83.0000 -124.9151 28

 16 omega   16.00   45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   82.0000  -74.4725 29

 17 omega   24.00  117.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   75.0000    0.0039 93

 18 omega   28.00  121.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   75.0000  162.8734 93

 19 omega   28.00  121.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   75.0000  109.5090 93

 20 omega   31.00  126.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000  -62.7127 95

 21 omega   38.00  125.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   64.0000   68.8260 87

 22 omega   31.00  126.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000   29.0849 95

 23 omega   32.00  125.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   76.0000  -34.6370 93

 24 omega   33.00  125.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   74.0000 -160.4908 92

 25 omega   31.00  126.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000 -128.8754 95

 26 omega   81.00  176.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 95

 27 omega   90.00  175.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -30.0000 85

 28 omega   81.00  176.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 95

 29 omega   81.00  176.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 95

 30 omega   81.00  176.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 95

 31 omega   81.00  176.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 95

 32 omega   90.00  175.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   30.0000 85

 33 omega   90.00  175.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -180.0000 85

 34 omega   90.00  175.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -150.0000 85

 35 omega   39.00  109.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  150.0000 70

 36 omega   90.00  175.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   90.0000 85

 37 omega   39.00  109.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 70

 38 omega   81.00  176.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 95

 39 omega   90.00  175.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -90.0000 85

 40 omega   81.00  176.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 95

 41 omega   81.00  176.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 95

 42 omega   40.00   98.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 58

 43 omega   81.00  176.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 95

 44 omega   81.00  159.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 78

 45 omega   90.00  166.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  150.0000 76

 46 omega   39.00   82.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 43

 47 omega   91.00  132.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   60.0000 41

 48 omega   39.00  116.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 77

 49 omega   82.00  108.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 26

 50 omega  125.00  175.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 50

 51 omega   72.00  134.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -120.0000 62

 52 omega   90.00  133.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  120.0000 43

 53 omega  140.00  168.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  120.0000 28

 54 omega   81.00  108.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 27

 55 omega   42.00   67.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -120.0000 25
;
_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      0.1203670000
_diffrn_orient_matrix_UB_12      -0.0139628000
_diffrn_orient_matrix_UB_13      0.0874575000
_diffrn_orient_matrix_UB_21      -0.0686263000
_diffrn_orient_matrix_UB_22      0.0743375000
_diffrn_orient_matrix_UB_23      0.1030734000
_diffrn_orient_matrix_UB_31      -0.0484499000
_diffrn_orient_matrix_UB_32      -0.1399887000
_diffrn_orient_matrix_UB_33      0.0460102000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            21649
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.686
_diffrn_reflns_theta_min         4.098
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.759
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68481
_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 light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_description       block
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details
;
 Flack x determined using 1787 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         4188
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0499
_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^)+(0.0940P)^2^+0.0830P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1275
_refine_ls_wR_factor_ref         0.1285
_reflns_Friedel_coverage         0.820
_reflns_Friedel_fraction_full    0.938
_reflns_Friedel_fraction_max     0.924
_reflns_number_gt                4111
_reflns_number_total             4188
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc02757e2.cif
_cod_data_source_block           fxm-kyl-9c-boc-2
_cod_depositor_comments
'Adding full bibliography for 1547942--1547944.cif.'
_cod_database_code               1547942
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H00D(0.057) H00E(0.057) H00I(0.078) H00J(0.07) H00L(0.081)
 H00M(0.089) H00N(0.089) H00O(0.121) H00P(0.1) H00A(0.17) H00B(0.17) H00C(0.17)
 H00F(0.155) H00G(0.155) H00H(0.155) H00K(0.152) H00Q(0.152) H00R(0.152)
 H00T(0.126) H00U(0.139) H00S(0.199) H00V(0.199) H00W(0.199)
 Fixed X: H00D(0.3992) H00E(0.3413) H00I(0.1333) H00J(0.177) H00L(0.0446)
 H00M(0.0693) H00N(0.0229) H00O(-0.0981) H00P(0.296) H00A(0.8395) H00B(0.8188)
 H00C(0.9255) H00F(0.5122) H00G(0.4661) H00H(0.3666) H00K(0.5577) H00Q(0.5842)
 H00R(0.6262) H00T(-0.0652) H00U(0.1266) H00S(0.2571) H00V(0.3588) H00W(0.3065)
 Fixed Y: H00D(0.1588) H00E(0.4249) H00I(0.3913) H00J(0.0943) H00L(0.0373)
 H00M(0.4164) H00N(0.1836) H00O(0.3226) H00P(0.1131) H00A(0.2591) H00B(0.1167)
 H00C(0.2174) H00F(0.7207) H00G(0.8734) H00H(0.7527) H00K(0.8401) H00Q(0.9334)
 H00R(0.7781) H00T(0.1295) H00U(0.0221) H00S(0.8849) H00V(0.9898) H00W(0.8733)
 Fixed Z: H00D(0.4565) H00E(0.5559) H00I(0.0055) H00J(0.3464) H00L(0.1735)
 H00M(0.5145) H00N(0.0075) H00O(0.6177) H00P(0.65) H00A(0.2408) H00B(0.3056)
 H00C(0.3582) H00F(-0.0709) H00G(-0.0914) H00H(-0.0938) H00K(0.2298)
 H00Q(0.1156) H00R(0.1173) H00T(0.7403) H00U(0.7485) H00S(0.0592) H00V(0.1145)
 H00W(0.1985)
;
_shelx_res_checksum              8653
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'