Highly Efficient Asymmetric Synthesis of Chiral γ-Alkenyl Butenolides Catalyzed by Chiral N,N′-Dioxide‒Scandium(III) Complexes
Ji, Jie; Lin, Lili; Tang, Qiong; Kang, Tengfei; Liu, Xiaohua; Feng, Xiaoming; ACS Catalysis 7 (2017) 3763–; doi:10.1021/acscatal.7b00590

data_4514096
_publ_section_title
;
 Highly Efficient Asymmetric Synthesis of Chiral \g-Alkenyl Butenolides
 Catalyzed by Chiral N,N&#x2032;-Dioxide--Scandium(III) Complexes
;
_journal_issue                   6
_journal_name_full               'ACS Catalysis'
_journal_page_first              3763
_journal_paper_doi               10.1021/acscatal.7b00590
_journal_volume                  7
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H10 O5'
_chemical_formula_sum            'C12 H10 O5'
_chemical_formula_weight         234.20
_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             2017-01-18
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.9658(2)
_cell_length_b                   6.8587(3)
_cell_length_c                   26.8770(10)
_cell_measurement_reflns_used    1884
_cell_measurement_temperature    293.52(10)
_cell_measurement_theta_max      72.2590
_cell_measurement_theta_min      6.5800
_cell_volume                     1099.74(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      293.52(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega   23.00   89.00   1.0000    3.3800
omega____ theta____ kappa____ phi______ frames
    -       36.0421 -125.0000 -150.0000 66

  2 omega  -32.00   63.00   1.0000    3.3800
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -77.0000  120.0000 95

  3 omega    9.00  104.00   1.0000    3.3800
omega____ theta____ kappa____ phi______ frames
    -       36.0421   77.0000   30.0000 95

  4 omega    7.00  107.00   1.0000    3.3800
omega____ theta____ kappa____ phi______ frames
    -       36.0421   19.0000 -120.0000 100

  5 omega   40.00   98.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 58

  6 omega   39.00  109.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 70

  7 omega   40.00   98.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 58

  8 omega   38.00   91.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 53

  9 omega   38.00   91.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 53

 10 omega   40.00   98.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 58

 11 omega   40.00   98.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 58

 12 omega  -31.00   -6.00   1.0000    3.3800
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -57.0000  -90.0000 25
;
_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      0.0873071000
_diffrn_orient_matrix_UB_12      0.0679311000
_diffrn_orient_matrix_UB_13      0.0510979000
_diffrn_orient_matrix_UB_21      0.0754017000
_diffrn_orient_matrix_UB_22      0.1947540000
_diffrn_orient_matrix_UB_23      -0.0232266000
_diffrn_orient_matrix_UB_31      -0.2309553000
_diffrn_orient_matrix_UB_32      0.0889985000
_diffrn_orient_matrix_UB_33      0.0116584000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            3539
_diffrn_reflns_point_group_measured_fraction_full 0.952
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        65.069
_diffrn_reflns_theta_max         65.069
_diffrn_reflns_theta_min         6.588
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.948
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50976
_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    1.415
_exptl_crystal_description       plate
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 565 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1777
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0509
_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^)+(0.1000P)^2^+0.0630P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1384
_refine_ls_wR_factor_ref         0.1424
_reflns_Friedel_coverage         0.577
_reflns_Friedel_fraction_full    0.882
_reflns_Friedel_fraction_max     0.882
_reflns_number_gt                1680
_reflns_number_total             1777
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs7b00590_si_004.cif
_cod_data_source_block           fxm-h-111-3
_cod_depositor_comments          'Adding full bibliography for 4514096.cif.'
_cod_original_cell_volume        1099.74(8)
_cod_database_code               4514096
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C48 H40 O20'
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C008(H008), C009(H009)
2.b Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00B(H00B), C00C(H00C), C00E(H00E), C00G(H00G)
2.c Idealised Me refined as rotating group:
 C00H(H00D,H00F,H00H)
;
_olex2_date_sample_data_collection 2017-01-18
_olex2_submission_special_instructions 'No special instructions were received'