A N,N′-dioxide/Mg(OTf)2complex catalyzed enantioselective α-addition of isocyanides to alkylidene malonates
Luo, Weiwei; Yuan, Xiao; Lin, Lili; Zhou, Pengfei; Liu, Xiaohua; Feng, Xiaoming; Chem. Sci. 7 (2016) 4736–; doi:10.1039/C6SC00689B

data_1543497
_publ_section_title
;
 A N,N&#x2032;-dioxide/Mg(OTf)2complex catalyzed enantioselective
 \a-addition of isocyanides to alkylidene malonates
;
_journal_issue                   7
_journal_name_full               'Chem. Sci.'
_journal_page_first              4736
_journal_paper_doi               10.1039/C6SC00689B
_journal_volume                  7
_journal_year                    2016
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C23 H29 N2 O6'
_chemical_formula_sum            'C23 H30 N2 O6'
_chemical_formula_weight         430.49
_chemical_name_systematic
'dimethyl 2-((4-tert-butyl-5-morpholinooxazol-2-yl)(phenyl)methyl)malonate'
_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_block_doi                 10.5517/cc1jjj9w
_audit_creation_date             2015-07-13
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-07-30 deposited with the CCDC.
2016-04-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.181(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.8375(4)
_cell_length_b                   9.9410(3)
_cell_length_c                   11.3983(4)
_cell_measurement_reflns_used    5052
_cell_measurement_temperature    293
_cell_measurement_theta_max      72.3230
_cell_measurement_theta_min      4.4940
_cell_volume                     1204.69(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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, 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
  1 omega   23.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421 -125.0000  120.0000 66

  2 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -57.0000  120.0000 84

  3 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -57.0000  -60.0000 84

  4 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   38.0000  120.0000 88

  5 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   57.0000    0.0000 84

  6 omega   23.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421 -125.0000 -120.0000 66

  7 omega   23.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421 -125.0000 -180.0000 66

  8 omega   23.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421 -125.0000  -60.0000 66

  9 omega    9.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   77.0000   30.0000 95

 10 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -57.0000 -150.0000 84

 11 omega   81.00  176.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 95

 12 omega   91.00  176.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 85

 13 omega   87.00  178.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  150.0000 91

 14 omega   90.00  175.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   90.0000 85

 15 omega   81.00  176.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 95

 16 omega   81.00  176.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 95

 17 omega   37.00  146.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000   30.0000 109

 18 omega   40.00   98.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 58

 19 omega   87.00  178.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   90.0000 91

 20 omega   41.00  126.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  150.0000 85

 21 omega   87.00  178.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  120.0000 91

 22 omega   70.00  178.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000   90.0000 108

 23 omega   40.00  103.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 63

 24 omega   39.00   65.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 26

 25 omega  126.00  171.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 45

 26 omega   86.00  111.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 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      0.1159482000
_diffrn_orient_matrix_UB_12      -0.0224511000
_diffrn_orient_matrix_UB_13      0.1001120000
_diffrn_orient_matrix_UB_21      0.0681703000
_diffrn_orient_matrix_UB_22      0.1168016000
_diffrn_orient_matrix_UB_23      -0.0495906000
_diffrn_orient_matrix_UB_31      -0.0537190000
_diffrn_orient_matrix_UB_32      0.0992777000
_diffrn_orient_matrix_UB_33      0.0808239000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11120
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.072
_diffrn_reflns_theta_max         67.072
_diffrn_reflns_theta_min         5.155
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.707
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39467
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_F_000             460
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent:  ethyl acetate/petroleum ether'
_exptl_crystal_size_max          1.0
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.5
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.084
_refine_ls_abs_structure_details
;
 Flack x determined using 1558 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         4143
_refine_ls_number_restraints     433
_refine_ls_restrained_S_all      1.154
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0735
_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^)+(0.1544P)^2^+0.0322P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1906
_refine_ls_wR_factor_ref         0.1967
_reflns_Friedel_coverage         0.828
_reflns_Friedel_fraction_full    0.930
_reflns_Friedel_fraction_max     0.930
_reflns_number_gt                3825
_reflns_number_total             4143
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6sc00689b2.cif
_cod_data_source_block           fxm-tick-zze
_cod_depositor_comments          'Adding full bibliography for 1543497.cif.'
_cod_original_cell_volume        1204.69(8)
_cod_database_code               1543497
_reflns_odcompleteness_completeness 99.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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. Uiso/Uaniso restraints and constraints
C008 \\sim C009 \\sim C00A \\sim C00B \\sim C00C \\sim C00D \\sim C00F \\sim
C00G \\sim C00H \\sim C00I \\sim C00J \\sim C00K \\sim C00L \\sim C00M \\sim
C00N \\sim C00O \\sim C00P \\sim C00Q \\sim C00R \\sim C00S \\sim C00T \\sim
C00U \\sim C00V: within 3.8A with sigma of 0.01 and sigma for terminal atoms of
0.02
3.a Ternary CH refined with riding coordinates:
 C00C(H00C), C00F(H00F)
3.b Secondary CH2 refined with riding coordinates:
 C00D(H00A,H00B), C00L(H00D,H00E), C00O(H00G,H00K)
3.c Aromatic/amide H refined with riding coordinates:
 C00H(H00H), C00I(H00I), C00J(H00J), C00M(H00M), C00P(H00P), C00Q(H00Q)
3.d Idealised Me refined as rotating group:
 C00R(H00L,H00N,H00O), C00S(H00R,H00S,H00T), C00T(H00U,H00V,H00W), C00U(H00X,
 H00Y,H), C00V(H00Z,HA,HB)
;
_shelx_res_checksum              308
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-07-13
_olex2_submission_special_instructions 'No special instructions were received'