N,N'-Dioxide-Scandium(III)-Catalyzed Asymmetric Aza-Friedel-Crafts Reaction of Sesamol with Aldimines.
Bai, Sha; Liao, Yuting; Lin, Lili; Luo, Weiwei; Liu, Xiaohua; Feng, Xiaoming; The Journal of organic chemistry 79 (2014) 10662–; doi:10.1021/jo5020036

data_4030109
_publ_section_title
;
 N,N'-Dioxide-Scandium(III)-Catalyzed Asymmetric Aza-Friedel-Crafts
 Reaction of Sesamol with Aldimines.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10662
_journal_paper_doi               10.1021/jo5020036
_journal_volume                  79
_journal_year                    2014
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C31 H34 F N O9 S'
_chemical_formula_sum            'C31 H34 F N O9 S'
_chemical_formula_weight         615.65
_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_Hall           'C 2c 2'
_space_group_name_H-M_alt        'C 2 2 21'
_symmetry_space_group_name_Hall  'C 2c 2'
_symmetry_space_group_name_H-M   'C 2 2 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-08-21
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.13480(19)
_cell_length_b                   17.3090(3)
_cell_length_c                   38.8028(5)
_cell_measurement_reflns_used    4965
_cell_measurement_temperature    293
_cell_measurement_theta_max      69.4150
_cell_measurement_theta_min      5.1030
_cell_volume                     6806.91(19)
_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    'olex2.solve (Bourhis et al., 2013)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details
;
  1 omega   23.00   90.00   1.0000   15.2800
omega____ theta____ kappa____ phi______ frames
    -       36.6671 -125.0000  -90.0000 67

  2 omega   20.00  104.00   1.0000   15.2800
omega____ theta____ kappa____ phi______ frames
    -       36.6671   57.0000  -60.0000 84

  3 omega   23.00   90.00   1.0000   15.2800
omega____ theta____ kappa____ phi______ frames
    -       36.6671 -125.0000  150.0000 67

  4 omega   39.00   98.00   1.0000   61.1100
omega____ theta____ kappa____ phi______ frames
    -      107.7694  -45.0000   60.0000 59

  5 omega   38.00   91.00   1.0000   61.1100
omega____ theta____ kappa____ phi______ frames
    -      107.7694  -30.0000 -120.0000 53

  6 omega   39.00   98.00   1.0000   61.1100
omega____ theta____ kappa____ phi______ frames
    -      107.7694  -45.0000  120.0000 59

  7 omega   38.00   91.00   1.0000   61.1100
omega____ theta____ kappa____ phi______ frames
    -      107.7694  -30.0000  150.0000 53

  8 omega   69.00  178.00   1.0000   61.1100
omega____ theta____ kappa____ phi______ frames
    -      107.7694   15.0000 -180.0000 109

  9 omega   10.00  104.00   1.0000   15.2800
omega____ theta____ kappa____ phi______ frames
    -       36.6671   77.0000 -180.0000 94

 10 omega   10.00  104.00   1.0000   15.2800
omega____ theta____ kappa____ phi______ frames
    -       36.6671   77.0000   60.0000 94

 11 omega   38.00  109.00   1.0000   61.1100
omega____ theta____ kappa____ phi______ frames
    -      107.7694  -94.0000    0.0000 71
;
_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      -0.0249748000
_diffrn_orient_matrix_UB_12      -0.0608603000
_diffrn_orient_matrix_UB_13      -0.0282159000
_diffrn_orient_matrix_UB_21      -0.1231564500
_diffrn_orient_matrix_UB_22      -0.0282190500
_diffrn_orient_matrix_UB_23      0.0195622000
_diffrn_orient_matrix_UB_31      -0.0854316000
_diffrn_orient_matrix_UB_32      0.0585100000
_diffrn_orient_matrix_UB_33      -0.0199536000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            13001
_diffrn_reflns_point_group_measured_fraction_full 0.913
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.059
_diffrn_reflns_theta_min         4.558
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.315
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81523
_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    1.201
_exptl_crystal_description
;
;
_exptl_crystal_F_000             2592
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.089
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details
;
 Flack x determined using 1748 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.024(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     395
_refine_ls_number_reflns         5600
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0714
_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^)+(0.1585P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1995
_refine_ls_wR_factor_ref         0.2123
_reflns_Friedel_coverage         0.702
_reflns_Friedel_fraction_full    0.846
_reflns_Friedel_fraction_max     0.857
_reflns_number_gt                4754
_reflns_number_total             5600
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5020036_si_001.cif
_cod_data_source_block           fxm-3-f-2boc
_cod_depositor_comments          'Adding full bibliography for 4030109.cif.'
_cod_database_code               4030109
_shelxl_version_number           2014-1
_reflns_odcompleteness_completeness 97.67
_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
2.a Ternary CH refined with riding coordinates:
 C42(H42)
2.b Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C15(H15), C18(H18), C20(H20), C23(H23), C25(H25), C34(H34),
 C41(H41), C43(H43), C45(H45)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C27(H27A,H27B,H27C), C28(H28A,H28B,
 H28C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C35(H35A,H35B,H35C)
;
_shelx_res_checksum              69004
_shelx_hkl_checksum              99552
_olex2_submission_special_instructions 'No special instructions were received'