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_7117280
_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         'C22 H19 N O4'
_chemical_formula_sum            'C22 H19 N O4'
_chemical_formula_weight         361.38
_chemical_name_systematic
'(R)-ethyl 2-hydroxy-4-phenyl-2-((2-phenyloxazol-5-yl)methyl)but-3-ynoate'
_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             2015-01-12
_audit_creation_method
;
Olex2 1.2
(compiled 2014.05.21 svn.r2940 for OlexSys, GUI svn.r4846)
;
_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                   9.8442(3)
_cell_length_b                   12.3537(3)
_cell_length_c                   16.5313(6)
_cell_measurement_reflns_used    5527
_cell_measurement_temperature    293
_cell_measurement_theta_max      72.6310
_cell_measurement_theta_min      4.4820
_cell_volume                     2010.41(11)
_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 0.990
_diffrn_measurement_details
;
  1 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171   57.0000 -120.0000 84

  2 omega  -33.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -38.0000   30.0000 88

  3 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171   57.0000  -90.0000 84

  4 omega   32.00   97.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171 -139.0000  -87.0000 65

  5 omega  -31.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -77.0000  120.0000 94

  6 omega  -31.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -77.0000 -120.0000 94

  7 omega   39.00  109.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 70

  8 omega   38.00   91.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 53

  9 omega   38.00   91.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 53

 10 omega   38.00   91.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 53

 11 omega   38.00   91.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 53

 12 omega   40.00   98.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 58

 13 omega   38.00   91.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 53

 14 omega   39.00  109.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 70

 15 omega   87.00  178.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   90.0000 91

 16 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171   57.0000    0.0000 84

 17 omega   20.00   92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171   57.0000  150.0000 72

 18 omega    2.00   29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171   91.0000   99.8498 27
;
_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      0.0838989000
_diffrn_orient_matrix_UB_12      0.1031717000
_diffrn_orient_matrix_UB_13      -0.0155487000
_diffrn_orient_matrix_UB_21      -0.1320788000
_diffrn_orient_matrix_UB_22      0.0661540000
_diffrn_orient_matrix_UB_23      -0.0079485000
_diffrn_orient_matrix_UB_31      0.0027699000
_diffrn_orient_matrix_UB_32      0.0232250000
_diffrn_orient_matrix_UB_33      0.0915101000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11269
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.926
_diffrn_reflns_theta_min         4.468
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.672
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43559
_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    1.194
_exptl_crystal_F_000             760
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethyl acetate/petroleum ether'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 1405 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3917
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0527
_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^)+(0.1100P)^2^+0.0260P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1417
_refine_ls_wR_factor_ref         0.1465
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.959
_reflns_number_gt                3559
_reflns_number_total             3917
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc02748a2.cif
_cod_data_source_block           fxm-vick-18f
_cod_database_code               7117280
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H001(0.105) H006(0.079) H00A(0.082) H00B(0.082) H00G(0.088)
 H00H(0.095) H00I(0.098) H00J(0.096) H00K(0.107) H00L(0.104) H00M(0.123)
 H00N(0.146) H00C(0.132) H00D(0.132) H00P(0.161) H00Q(0.194) H00E(0.3)
 H00F(0.3) H00O(0.3)
 Fixed X: H001(0.3857) H006(0.4136) H00A(0.4513) H00B(0.3291) H00G(0.191)
 H00H(0.0647) H00I(0.0457) H00J(-0.0927) H00K(-0.0809) H00L(0.875) H00M(1.1038)
 H00N(1.2149) H00C(0.7198) H00D(0.7939) H00P(0.8753) H00Q(1.1023) H00E(0.6603)
 H00F(0.8181) H00O(0.7245)
 Fixed Y: H001(0.5287) H006(0.8927) H00A(0.7008) H00B(0.7323) H00G(0.4303)
 H00H(0.3255) H00I(0.3114) H00J(0.2018) H00K(0.2073) H00L(0.9597) H00M(0.9411)
 H00N(0.7834) H00C(0.4017) H00D(0.5146) H00P(0.6611) H00Q(0.6445) H00E(0.436)
 H00F(0.4493) H00O(0.5519)
 Fixed Z: H001(0.7205) H006(0.692) H00A(0.5311) H00B(0.5872) H00G(0.381)
 H00H(0.5967) H00I(0.3193) H00J(0.3948) H00K(0.5331) H00L(0.7471) H00M(0.7773)
 H00N(0.7499) H00C(0.5332) H00D(0.5387) H00P(0.6554) H00Q(0.688) H00E(0.4021)
 H00F(0.4102) H00O(0.4072)
;
_shelx_res_checksum              79127
_shelx_hkl_checksum              69651
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'