Chiral Lewis acid-catalyzed enantioselective cyclopropanation and C-H insertion reactions of vinyl ketones with α-diazoesters.
Zhao, Peng; Wu, Simeng; Ke, Chaoqi; Liu, Xiaohua; Feng, Xiaoming; Chemical communications (Cambridge, England) 54 (2018) 9837–9840; doi:10.1039/c8cc05420g

data_7122188
_publ_section_title
;
 Chiral Lewis acid-catalyzed enantioselective cyclopropanation and C-H
 insertion reactions of vinyl ketones with \a-diazoesters.
;
_journal_issue                   70
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9837
_journal_page_last               9840
_journal_paper_doi               10.1039/c8cc05420g
_journal_volume                  54
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C32 H30 N2 O4 S'
_chemical_formula_sum            'C32 H30 N2 O4 S'
_chemical_formula_weight         538.64
_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_creation_date             2017-07-19
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-05-17 deposited with the CCDC.
2018-08-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.782(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.7057(2)
_cell_length_b                   10.0310(3)
_cell_length_c                   14.8723(4)
_cell_measurement_reflns_used    4224
_cell_measurement_temperature    299.1(3)
_cell_measurement_theta_max      72.6270
_cell_measurement_theta_min      4.4040
_cell_volume                     1434.60(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, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      299.1(3)
_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 0.981
_diffrn_measurement_details
;
  1 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   57.0000 -150.0000 84

  2 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671 -125.0000  -90.0000 67

  3 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -99.0000 -120.0000 74

  4 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   57.0000    0.0000 84

  5 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   57.0000 -180.0000 84

  6 omega  -31.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -77.0000   60.0000 94

  7 omega   39.00  109.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 70

  8 omega   81.00  176.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 95

  9 omega   38.00   91.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 53

 10 omega   91.00  176.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 85

 11 omega   38.00   91.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 53

 12 omega   39.00  109.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   60.0000 70

 13 omega   40.00   98.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 58

 14 omega   87.00  178.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   90.0000 91

 15 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   57.0000  -60.0000 84

 16 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -57.0000  -60.0000 84

 17 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   57.0000   90.0000 84
;
_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      0.0474132000
_diffrn_orient_matrix_UB_12      -0.0308021000
_diffrn_orient_matrix_UB_13      -0.0925533000
_diffrn_orient_matrix_UB_21      -0.0890810000
_diffrn_orient_matrix_UB_22      -0.1276143000
_diffrn_orient_matrix_UB_23      -0.0076533000
_diffrn_orient_matrix_UB_31      -0.1244760000
_diffrn_orient_matrix_UB_32      0.0796541000
_diffrn_orient_matrix_UB_33      -0.0480001000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8332
_diffrn_reflns_point_group_measured_fraction_full 0.873
_diffrn_reflns_point_group_measured_fraction_max 0.841
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.589
_diffrn_reflns_theta_min         4.598
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.314
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46227
_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    1.247
_exptl_crystal_description       plate
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 1534 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.073(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         4788
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0557
_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^)+(0.1076P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1466
_refine_ls_wR_factor_ref         0.1516
_reflns_Friedel_coverage         0.616
_reflns_Friedel_fraction_full    0.731
_reflns_Friedel_fraction_max     0.683
_reflns_number_gt                4329
_reflns_number_total             4788
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc05420g2.cif
_cod_data_source_block           fxm-wsm-182
_cod_depositor_comments
'Adding full bibliography for 7122187--7122188.cif.'
_cod_database_code               7122188
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.96
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00G(H00G)
2.b Secondary CH2 refined with riding coordinates:
 C00T(H00B,H00D)
2.c Aromatic/amide H refined with riding coordinates:
 N007(H007), C009(H009), C00A(H00A), C00C(H00C), C00F(H00F), C00H(H00H),
 C00I(H00I), C00J(H00J), C00L(H00L), C00M(H00M), C00O(H00O), C00R(H00R),
 C00S(H00S), C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y),
 C010(H010), C011(H011), C012(H012)
2.d Idealised Me refined as rotating group:
 C00Z(H00E,H00K,H00N), C013(H01A,H01B,H01C)
;
_olex2_date_sample_data_collection 2017-07-18
_olex2_submission_special_instructions 'No special instructions were received'