Chiral Phosphoric Acid Catalyzed Asymmetric Oxidative Dearomatization of Naphthols with Quinones.
Zhu, Gongming; Bao, Guangjun; Li, Yiping; Yang, Junxian; Sun, Wangsheng; Li, Jing; Hong, Liang; Wang, Rui; Organic letters 18 (2016) 5288–5291; doi:10.1021/acs.orglett.6b02609

data_1555826
_publ_section_title
;
 Chiral Phosphoric Acid Catalyzed Asymmetric Oxidative Dearomatization of
 Naphthols with Quinones.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              5288
_journal_page_last               5291
_journal_paper_doi               10.1021/acs.orglett.6b02609
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C18 H14 O3'
_chemical_formula_sum            'C18 H14 O3'
_chemical_formula_weight         278.29
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-01-13
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                72.019(7)
_cell_angle_beta                 79.887(7)
_cell_angle_gamma                74.428(7)
_cell_formula_units_Z            2
_cell_length_a                   7.6607(7)
_cell_length_b                   9.2315(7)
_cell_length_c                   11.1270(8)
_cell_measurement_reflns_used    2491
_cell_measurement_temperature    293.60(10)
_cell_measurement_theta_max      69.0600
_cell_measurement_theta_min      4.1390
_cell_volume                     717.29(11)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.60(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_details
;
  1 omega  120.00  148.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       80.0000   56.0000   13.4054 28

  2 omega  133.00  168.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   71.0000   66.7909 35

  3 omega  150.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 26

  4 omega  109.00  135.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   74.0000   99.8065 26

  5 omega   90.00  140.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   76.0000   55.8104 50

  6 omega   90.00  118.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000    0.0000 28

  7 omega   73.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   71.0000   66.7909 34

  8 omega   86.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000   30.0000 26

  9 omega   84.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000   60.0000 93

 10 omega  110.00  154.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 44

 11 omega  107.00  164.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 57

 12 omega  104.00  130.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       88.0000   75.0000 -132.2110 26

 13 omega  100.00  137.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   49.0000 -144.5057 37

 14 omega   86.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000 -180.0000 26

 15 omega   79.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 26

 16 omega   78.00  170.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 92

 17 omega  105.00  132.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  -90.0000 27

 18 omega   83.00  172.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 89

 19 omega   86.00  144.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000  120.0000 58

 20 omega   79.00  162.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 83

 21 omega   83.00  122.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000  120.0000 39

 22 omega   78.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 26

 23 omega   69.00  100.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       96.0000   72.0000   98.2853 31

 24 omega   72.00   97.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       92.0000   57.0000  155.5822 25

 25 omega   45.00   83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   74.0000   99.8065 38

 26 omega   44.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   76.0000   55.8104 33

 27 omega   59.00   85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       80.0000   56.0000   13.4054 26

 28 omega   68.00   94.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       88.0000   59.0000   14.9017 26

 29 omega   78.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 71

 30 omega   78.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 28

 31 omega   80.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 97

 32 omega   81.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   76.0000 -101.1669 25

 33 omega   78.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 99

 34 omega   59.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       84.0000   70.0000  -51.1693 47

 35 omega   63.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       88.0000   75.0000 -132.2110 27

 36 omega   56.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   49.0000  -70.7980 51

 37 omega   48.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   42.0000 -103.9842 26

 38 omega   50.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   49.0000 -144.5057 27

 39 omega   25.00   51.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000 -120.0000 26

 40 omega   24.00   52.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  -90.0000 28

 41 omega   28.00   57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  -60.0000 29

 42 omega   35.00   73.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   72.0000  -17.4517 38

 43 omega   21.00   49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   78.0000   64.1490 28

 44 omega   27.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   75.0000  112.7224 26

 45 omega   40.00  126.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   74.0000  142.0606 86

 46 omega   40.00  125.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000    0.0000 85

 47 omega   78.00  114.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000    0.0000 36

 48 omega   52.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000    0.0000 25

 49 omega   23.00   83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000  -60.0000 60

 50 omega   43.00  134.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -120.0000 91

 51 omega   38.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -120.0000 65

 52 omega   40.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -120.0000 53

 53 omega   25.00   51.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000    0.0000 26

 54 omega    7.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       44.0000   89.0000  -17.5544 26

 55 omega  -11.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000   30.0000 64

 56 omega   20.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   19.0000  -30.0000 33

 57 omega   -4.00   21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0000   96.0000 -109.6576 25

 58 omega   27.00   56.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000 -180.0000 29

 59 omega   -6.00   19.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -38.0000  -90.0000 25

 60 omega   71.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  150.0000 32

 61 omega    2.00   94.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -99.0000   30.0000 92

 62 omega  -12.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -38.0000   90.0000 89

 63 omega    3.00   28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0000   91.0000  127.5930 25

 64 omega  -26.00   11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0000  107.0000   82.9376 37

 65 omega  -44.00   -9.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   19.0000  -30.0000 35

 66 omega  -72.00  -16.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -38.0000  -90.0000 56
;
_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      0.0686297000
_diffrn_orient_matrix_UB_12      -0.1065432000
_diffrn_orient_matrix_UB_13      0.1272786000
_diffrn_orient_matrix_UB_21      0.1440202000
_diffrn_orient_matrix_UB_22      0.0949059000
_diffrn_orient_matrix_UB_23      -0.0155194000
_diffrn_orient_matrix_UB_31      -0.1363129000
_diffrn_orient_matrix_UB_32      0.1101126000
_diffrn_orient_matrix_UB_33      0.0704760000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8746
_diffrn_reflns_point_group_measured_fraction_full 0.879
_diffrn_reflns_point_group_measured_fraction_max 0.854
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.915
_diffrn_reflns_theta_min         4.199
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.708
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86853
_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    1.289
_exptl_crystal_description       block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1179 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.29(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         4653
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0429
_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^)+(0.0503P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.1185
_reflns_Friedel_coverage         0.776
_reflns_Friedel_fraction_full    0.776
_reflns_Friedel_fraction_max     0.747
_reflns_number_gt                3320
_reflns_number_total             4653
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02609_si_001.cif
_cod_data_source_block           zhgm_0111
_cod_database_code               1555826
_reflns_odcompleteness_completeness 99.02
_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:
 C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C13(H13), C14(H14), C16(H16),
 C21(H21), C23(H23), C24(H24), C25(H25), C26(H26), C30(H30), C32(H32), C33(H33)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C35(H35A,H35B,H35C), C36(H36A,H36B,
 H36C)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-01-12
_olex2_submission_special_instructions 'No special instructions were received'