Catalytic Desymmetrization of meso-Aziridines with Benzofuran-2(3H)-Ones Employing a Simple In Situ-Generated Magnesium Catalyst
Li, Dan; Wang, Linqing; Yang, Dongxu; Zhang, Bangzhi; Wang, Rui; ACS Catalysis 5 (2015) 7432–; doi:10.1021/acscatal.5b02177

data_4516693
_publ_section_title
;
 Catalytic Desymmetrization of meso-Aziridines with Benzofuran-2(3H)-Ones
 Employing a Simple In Situ-Generated Magnesium Catalyst
;
_journal_issue                   12
_journal_name_full               'ACS Catalysis'
_journal_page_first              7432
_journal_paper_doi               10.1021/acscatal.5b02177
_journal_volume                  5
_journal_year                    2015
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C26 H24 N2 O3'
_chemical_formula_sum            'C26 H24 N2 O3'
_chemical_formula_weight         412.47
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-07-31
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.604(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.4911(4)
_cell_length_b                   9.8015(3)
_cell_length_c                   12.0673(5)
_cell_measurement_reflns_used    8990
_cell_measurement_temperature    300.79(10)
_cell_measurement_theta_max      69.7880
_cell_measurement_theta_min      4.7720
_cell_volume                     1091.09(7)
_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)'
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_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
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_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
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_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
  1 omega  -21.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  -60.0000 90

  2 omega  -69.00   21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000   90.0000 90

  3 omega  -22.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   61.0000  136.0000 90

  4 omega  -15.00   75.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000 -120.0000 90

  5 omega   33.00  123.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  -60.0000 90

  6 omega   23.00  111.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000 -180.0000 88

  7 omega  -15.00   75.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  -30.0000 90

  8 omega   33.00  123.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  120.0000 90

  9 omega   33.00  123.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000   30.0000 90

 10 omega   36.00  116.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -120.0000 80

 11 omega  101.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  112.0000   13.0000 77

 12 omega   35.00   94.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -120.0000 59

 13 omega   38.00  138.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -60.0000 100

 14 omega   36.00  116.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000    0.0000 80

 15 omega   38.00  104.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000   90.0000 66

 16 omega   36.00  116.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 80

 17 omega   36.00  116.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 80

 18 omega   86.00  176.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000 -150.0000 90

 19 omega   36.00  116.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -60.0000 80

 20 omega   35.00   94.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000    0.0000 59

 21 omega   36.00   93.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000   30.0000 57

 22 omega   78.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 100

 23 omega  100.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  120.0000 78

 24 omega  100.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   90.0000 78

 25 omega   78.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 100

 26 omega   74.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000  -60.0000 104

 27 omega  -69.00   21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000 -180.0000 90

 28 omega  -44.00   73.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   19.0000   90.0000 117

 29 omega   24.00  124.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000   60.0000 100

 30 omega   24.00  124.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000 -120.0000 100

 31 omega  -15.00   75.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  150.0000 90

 32 omega   24.00  124.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000 -150.0000 100

 33 omega   24.00  124.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  -30.0000 100

 34 omega   24.00  124.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  150.0000 100

 35 omega   78.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 100

 36 omega   78.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 100

 37 omega   78.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 100

 38 omega   86.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000   30.0000 92

 39 omega   78.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 100

 40 omega   86.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000 -120.0000 92

 41 omega   86.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  120.0000 92

 42 omega   78.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 100

 43 omega   78.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 100

 44 omega   82.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000    0.0000 96

 45 omega   78.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 100

 46 omega   78.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0710948000
_diffrn_orient_matrix_UB_12      -0.1293235000
_diffrn_orient_matrix_UB_13      -0.0349069000
_diffrn_orient_matrix_UB_21      0.0574919000
_diffrn_orient_matrix_UB_22      0.0836447000
_diffrn_orient_matrix_UB_23      -0.0881908000
_diffrn_orient_matrix_UB_31      0.1396959000
_diffrn_orient_matrix_UB_32      0.0312933000
_diffrn_orient_matrix_UB_33      0.0909042000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19261
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.161
_diffrn_reflns_theta_min         3.769
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.662
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83643
_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    1.255
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 1569 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4090
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.120
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0481
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0741P)^2^+0.2014P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1351
_refine_ls_wR_factor_ref         0.1407
_reflns_Friedel_coverage         0.868
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                3688
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_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs5b02177_si_002.cif
_cod_data_source_block           lidan0730
_cod_original_cell_volume        1091.10(7)
_cod_database_code               4516693
_reflns_odcompleteness_completeness 99.86
_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, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C3(H3), C4(H4), C18(H18), C19(H19), C20(H20),
 C21(H21), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28)
;
_shelx_res_checksum              79691
_shelx_hkl_checksum              50544
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-07-30
_olex2_submission_special_instructions 'No special instructions were received'