A catalytic asymmetric carbonyl-ene reaction of beta,gamma-unsaturated alpha-ketoesters with 5-methyleneoxazolines
Weiwei Luo; Jiannan Zhao; Jie Ji; Lili Lin; Xiaohua Liu; Hongjiang Mei; Xiaoming Feng; Chem.Commun. 51 (2015) 10042–; doi:10.1039/C5cc02748A

data_7117279
_publ_section_title
;
 A catalytic asymmetric carbonyl-ene reaction of beta,gamma-unsaturated
 alpha-ketoesters with 5-methyleneoxazolines
;
_journal_name_full               Chem.Commun.
_journal_page_first              10042
_journal_paper_doi               10.1039/C5cc02748A
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C21 H19 N O4'
_chemical_formula_sum            'C21 H19 N O4'
_chemical_formula_weight         349.37
_chemical_name_systematic
'(R,E)-methyl 2-hydroxy-4-phenyl-2-((2-phenyloxazol-5-yl)methyl)but-3-enoate'
_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     direct
_audit_creation_date             2015-01-05
_audit_creation_method
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Olex2 1.2
(compiled 2014.12.26 svn.r3119 for OlexSys, GUI svn.r4975)
;
_audit_update_record
;
2015-02-03 deposited with the CCDC.
2015-05-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7332(3)
_cell_length_b                   12.3327(3)
_cell_length_c                   15.1571(4)
_cell_measurement_reflns_used    5269
_cell_measurement_temperature    115(7)
_cell_measurement_theta_max      72.6150
_cell_measurement_theta_min      4.6330
_cell_volume                     1819.41(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
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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_environment      N~2~
_diffrn_ambient_temperature      115(7)
_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 0.987
_diffrn_measurement_details
;
  1 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000 -180.0000 67

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

  3 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000   30.0000 74

  4 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000  -90.0000 94

  5 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000  -60.0000 84

  6 omega   40.00   98.00   1.0000    1.1100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 58

  7 omega   90.00  175.00   1.0000    1.1100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   90.0000 85

  8 omega   40.00  135.00   1.0000    1.1100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -90.0000 95

  9 omega   91.00  176.00   1.0000    1.1100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -120.0000 85

 10 omega   38.00   91.00   1.0000    1.1100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 53

 11 omega   38.00   91.00   1.0000    1.1100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 53

 12 omega   38.00   91.00   1.0000    1.1100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 53

 13 omega   57.00  150.00   1.0000    1.1100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   30.0000 93

 14 omega   91.00  176.00   1.0000    1.1100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -150.0000 85

 15 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000   90.0000 94
;
_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      0.1123294000
_diffrn_orient_matrix_UB_12      0.0870604000
_diffrn_orient_matrix_UB_13      -0.0099240000
_diffrn_orient_matrix_UB_21      0.0747668000
_diffrn_orient_matrix_UB_22      -0.0718378000
_diffrn_orient_matrix_UB_23      -0.0678377000
_diffrn_orient_matrix_UB_31      -0.0826648000
_diffrn_orient_matrix_UB_32      0.0533299000
_diffrn_orient_matrix_UB_33      -0.0751499000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10033
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.857
_diffrn_reflns_theta_min         4.622
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.723
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42988
_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    1.275
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethyl acetate/ petroleum ether'
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.100
_refine_ls_abs_structure_details
;
 Flack x determined using 1384 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3555
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0500
_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^)+(0.0954P)^2^+0.0254P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1239
_refine_ls_wR_factor_ref         0.1267
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.970
_reflns_number_gt                3410
_reflns_number_total             3555
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc02748a2.cif
_cod_data_source_block           fxm-vick-10c-120k
_cod_original_cell_volume        1819.42(8)
_cod_database_code               7117279
_reflns_odcompleteness_completeness 99.89
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00A(H00A,H00B)
2.b Aromatic/amide H refined with riding coordinates:
 C006(H006), C007(H007), C00B(H00C), C00G(H00G), C00H(H00H), C00I(H00I),
 C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O),
 C00P(H00P)
2.c Idealised Me refined as rotating group:
 C00Q(H00D,H00E,H00F)
2.d Idealised tetrahedral OH refined as rotating group:
 O001(H001)
;
_shelx_res_checksum              47405
_shelx_hkl_checksum              83675
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'