Kinetic resolution of 2,3-epoxy 3-aryl ketones via catalytic asymmetric ring-opening with pyrazole derivatives
Tianyu Huang; Lili Lin; Xiaolei Hu; Jianfeng Zheng; Xiaohua Liu; Xiaoming Feng; Chem.Commun. 51 (2015) 11374–; doi:10.1039/C5cc02179K

data_7117412
_publ_section_title
;
 Kinetic resolution of 2,3-epoxy 3-aryl ketones via catalytic asymmetric
 ring-opening with pyrazole derivatives
;
_journal_name_full               Chem.Commun.
_journal_page_first              11374
_journal_paper_doi               10.1039/C5cc02179K
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C26 H23 N3 O4'
_chemical_formula_sum            'C26 H22 N3 O4'
_chemical_formula_weight         440.47
_chemical_name_systematic
;
 ? 
;
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-11-18
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2014-11-18 deposited with the CCDC.
2015-04-27 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.97760(10)
_cell_length_b                   12.83530(10)
_cell_length_c                   25.7684(3)
_cell_measurement_reflns_used    6556
_cell_measurement_temperature    293
_cell_measurement_theta_max      72.1970
_cell_measurement_theta_min      4.8630
_cell_volume                     2307.81(5)
_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-1997 (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega    1.00   75.00   1.0000    5.2050
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000  -30.0000 74

  2 omega    1.00   75.00   1.0000    5.2050
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000    0.0000 74

  3 omega  -31.00   53.00   1.0000    5.2050
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -57.0000   60.0000 84

  4 omega    1.00   28.00   1.0000    5.2050
omega____ theta____ kappa____ phi______ frames
    -       36.5421   92.0000  168.9230 27

  5 omega   10.00  104.00   1.0000    5.2050
omega____ theta____ kappa____ phi______ frames
    -       36.5421   77.0000    0.0000 94

  6 omega   38.00   91.00   1.0000   20.8150
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 53

  7 omega   90.00  175.00   1.0000   20.8150
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -60.0000 85

  8 omega   38.00   91.00   1.0000   20.8150
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 53

  9 omega   38.00  116.00   1.0000   20.8150
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -120.0000 78

 10 omega   40.00   98.00   1.0000   20.8150
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 58

 11 omega   40.00   98.00   1.0000   20.8150
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 58

 12 omega   20.00  104.00   1.0000    5.2050
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000 -150.0000 84

 13 omega   20.00  104.00   1.0000    5.2050
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000  120.0000 84

 14 omega   20.00  104.00   1.0000    5.2050
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000  -60.0000 84

 15 omega  -33.00   55.00   1.0000    5.2050
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -38.0000 -150.0000 88

 16 omega    1.00   75.00   1.0000    5.2050
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000 -150.0000 74

 17 omega   87.00  164.00   1.0000   20.8150
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  120.0000 77
;
_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      -0.0650489000
_diffrn_orient_matrix_UB_12      0.0984666000
_diffrn_orient_matrix_UB_13      0.0292841000
_diffrn_orient_matrix_UB_21      0.0049402000
_diffrn_orient_matrix_UB_22      -0.0608111000
_diffrn_orient_matrix_UB_23      0.0515257000
_diffrn_orient_matrix_UB_31      0.2109649000
_diffrn_orient_matrix_UB_32      0.0317813000
_diffrn_orient_matrix_UB_33      0.0078225000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            12044
_diffrn_reflns_theta_full        67.07
_diffrn_reflns_theta_max         67.07
_diffrn_reflns_theta_min         4.86
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.708
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85312
_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    1.268
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             924
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         4004
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0446
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0911P)^2^+0.1214P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1249
_refine_ls_wR_factor_ref         0.1288
_reflns_number_gt                3710
_reflns_number_total             4004
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc02179k2.cif
_cod_data_source_block           1
_cod_database_code               7117412
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C14(H14),
 C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C26(H26A,H26B,H26C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'