Chiral N,N’-Dioxide/Sc(OTf)3 Complex-Catalyzed Asymmetric Dearomatization of β-Naphthols
Ge, Shulin; Kang, Tengfei; Lin, Lili; Zhang, Xiying; Zhao, Peng; Liu, Xiaohua; Feng, Xiaoming; Chem. Commun.  (2017) –; doi:10.1039/C7CC06388A

data_7120748
_publ_section_title
;
 Chiral N,N&#x2019;-Dioxide/Sc(OTf)3 Complex-Catalyzed Asymmetric
 Dearomatization of \b-Naphthols
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC06388A
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H22 O2'
_chemical_formula_sum            'C27 H22 O2'
_chemical_formula_weight         378.44
_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             2016-08-24
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2017-03-21 deposited with the CCDC.
2017-10-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.177(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.7287(3)
_cell_length_b                   36.9509(16)
_cell_length_c                   8.6433(5)
_cell_measurement_reflns_used    7717
_cell_measurement_temperature    297.0(5)
_cell_measurement_theta_max      71.5690
_cell_measurement_theta_min      4.7910
_cell_volume                     2074.04(19)
_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      297.0(5)
_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 0.990
_diffrn_measurement_details
;
  1 omega  -35.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.9171  -19.0000 -180.0000 100

  2 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.9171   57.0000 -150.0000 84

  3 omega    9.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.9171   77.0000  -90.0000 94

  4 omega   23.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.9171 -125.0000   90.0000 66

  5 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.9171   57.0000  150.0000 84

  6 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.9171   38.0000 -120.0000 88

  7 omega    9.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.9171   77.0000 -150.0000 94

  8 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.9171   38.0000    0.0000 88

  9 omega  -35.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.9171  -19.0000  -30.0000 100

 10 omega  -32.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.9171  -77.0000  -90.0000 95

 11 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.9171  -99.0000 -120.0000 74

 12 omega   81.00  176.00   1.0000    2.5500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 95

 13 omega   90.00  175.00   1.0000    2.5500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -180.0000 85

 14 omega   40.00   98.00   1.0000    2.5500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  150.0000 58

 15 omega   81.00  176.00   1.0000    2.5500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 95

 16 omega   39.00  109.00   1.0000    2.5500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 70

 17 omega   46.00   90.00   1.0000    2.5500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 44

 18 omega  100.00  136.00   1.0000    2.5500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  120.0000 36

 19 omega   81.00  107.00   1.0000    2.5500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 26

 20 omega  150.00  175.00   1.0000    2.5500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -150.0000 25

 21 omega  126.00  161.00   1.0000    2.5500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -120.0000 35

 22 omega   90.00  116.00   1.0000    2.5500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -150.0000 26

 23 omega   90.00  177.00   1.0000    2.5500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -90.0000 87

 24 omega   93.00  140.00   1.0000    2.5500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  120.0000 47

 25 omega   87.00  113.00   1.0000    2.5500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -180.0000 26

 26 omega   91.00  116.00   1.0000    2.5500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -120.0000 25

 27 omega   40.00   97.00   1.0000    2.5500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 57

 28 omega   94.00  162.00   1.0000    2.5500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   30.0000 68

 29 omega   87.00  116.00   1.0000    2.5500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -120.0000 29

 30 omega   96.00  122.00   1.0000    2.5500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -180.0000 26

 31 omega   93.00  119.00   1.0000    2.5500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  150.0000 26

 32 omega  131.00  175.00   1.0000    2.5500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 44

 33 omega   91.00  117.00   1.0000    2.5500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  150.0000 26

 34 omega   90.00  130.00   1.0000    2.5500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -120.0000 40

 35 omega   81.00  107.00   1.0000    2.5500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 26

 36 omega   90.00  122.00   1.0000    2.5500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  150.0000 32

 37 omega   40.00   91.00   1.0000    2.5500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 51

 38 omega   88.00  114.00   1.0000    2.5500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -150.0000 26

 39 omega   40.00   66.00   1.0000    2.5500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 26

 40 omega   91.00  148.00   1.0000    2.5500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -30.0000 57

 41 omega   74.00  100.00   1.0000    2.5500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -120.0000 26

 42 omega   83.00  109.00   1.0000    2.5500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   23.0000 -157.6189 26
;
_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      0.1429072000
_diffrn_orient_matrix_UB_12      0.0240242000
_diffrn_orient_matrix_UB_13      -0.0693427000
_diffrn_orient_matrix_UB_21      0.1442037000
_diffrn_orient_matrix_UB_22      0.0049438000
_diffrn_orient_matrix_UB_23      0.1693896000
_diffrn_orient_matrix_UB_31      0.1228038000
_diffrn_orient_matrix_UB_32      -0.0337242000
_diffrn_orient_matrix_UB_33      -0.0244523000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       -45
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            22516
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.569
_diffrn_reflns_theta_min         4.787
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.588
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49190
_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    1.212
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.7
_exptl_crystal_size_min          0.6
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 2767 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     527
_refine_ls_number_reflns         7821
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0599
_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^)+(0.1015P)^2^+0.1186P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1578
_refine_ls_wR_factor_ref         0.1653
_reflns_Friedel_coverage         0.882
_reflns_Friedel_fraction_full    0.938
_reflns_Friedel_fraction_max     0.903
_reflns_number_gt                7043
_reflns_number_total             7821
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc06388a2.cif
_cod_data_source_block           fxm-c-na-k18
_cod_depositor_comments
;

2018-02-18
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        2074.05(19)
_cod_original_formula_moiety     '2(C27 H22 O2)'
_cod_original_formula_sum        'C54 H44 O4'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     756.89
_cod_database_code               7120748
_reflns_odcompleteness_completeness 99.89
_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 Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00E(H00E), C00F(H00F), C00H(H00H), C00I(H00I), C00J(H00J),
 C00K(H00K), C00L(H00L), C00O(H00O), C00P(H00P), C00Q(H00Q), C00T(H00T),
 C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y), C010(H010), C011(H011),
 C012(H012), C013(H013), C014(H014), C017(H017), C018(H018), C01A(H01d),
 C01B(H01n), C01D(H01r), C01E(H01E), C01H(H01H), C01I(H01I), C01J(H01J),
 C01K(H01K), C01L(H01L)
2.b Idealised Me refined as rotating group:
 C019(H01a,H01b,H01c), C01C(H01o,H01p,H01q), C01F(H01s,H01t,H01u), C01M(H01f,
 H01g,H01m)
;
_shelx_res_checksum              41176
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-08-23
_olex2_submission_special_instructions 'No special instructions were received'