Chiral Cobalt(II) Complex Catalyzed Friedel-Crafts-Aromatization for Synthesis of Axially Chiral Biaryldiols
Xu, Chaoran; Zheng, Haifeng; Hu, Bowen; Liu, Xiaohua; Lin, Lili; Feng, Xiaoming; Chem. Commun.  (2017) –; doi:10.1039/C7CC05266A

data_7120520
_publ_section_title
;
 Chiral Cobalt(II) Complex Catalyzed Friedel-Crafts-Aromatization for
 Synthesis of Axially Chiral Biaryldiols
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC05266A
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H20 O5'
_chemical_formula_sum            'C21 H20 O5'
_chemical_formula_weight         352.37
_chemical_name_systematic
'butyl (aR)-3,6-dihydroxy-2-(2-hydroxynaphthalen-1-yl)benzoate'
_chemical_properties_physical
', Air-sensitive,Heat-sensitive,Oxygen-sensitive'
_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_block_doi                 10.5517/ccdc.csd.cc1p26ml
_audit_creation_date             2017-03-23
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_audit_update_record
;
2017-05-20 deposited with the CCDC.
2017-08-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.576(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.0345(2)
_cell_length_b                   12.6015(4)
_cell_length_c                   9.2114(3)
_cell_measurement_reflns_used    4923
_cell_measurement_temperature    290.64(10)
_cell_measurement_theta_max      72.5340
_cell_measurement_theta_min      5.0310
_cell_volume                     889.09(5)
_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      290.64(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -57.0000 -180.0000 84

  2 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -99.0000  120.0000 74

  3 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   57.0000  150.0000 84

  4 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   57.0000   60.0000 84

  5 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   57.0000  -60.0000 84

  6 omega   23.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421 -125.0000  120.0000 66

  7 omega    9.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   77.0000  -60.0000 95

  8 omega    9.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   77.0000 -150.0000 95

  9 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   38.0000  -90.0000 88

 10 omega   23.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421 -125.0000  -90.0000 66

 11 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   38.0000   90.0000 88

 12 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   57.0000  -30.0000 84

 13 omega   90.00  175.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -30.0000 85

 14 omega   81.00  176.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 95

 15 omega   81.00  176.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 95

 16 omega   81.00  176.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 95

 17 omega   87.00  178.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000    0.0000 91

 18 omega   43.00  134.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  120.0000 91

 19 omega   97.00  123.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -30.0000 26

 20 omega   90.00  119.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   30.0000 29

 21 omega   87.00  114.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -90.0000 27

 22 omega   43.00  109.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 66

 23 omega   87.00  117.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -30.0000 30

 24 omega  126.00  169.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 43

 25 omega   91.00  117.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -90.0000 26

 26 omega   81.00  106.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 25

 27 omega   90.00  116.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000    0.0000 26

 28 omega  129.00  176.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 47

 29 omega   91.00  117.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -60.0000 26

 30 omega  125.00  157.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 32

 31 omega   91.00  117.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -60.0000 26

 32 omega   81.00  107.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 26

 33 omega   81.00  107.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 26

 34 omega   93.00  121.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   30.0000 28

 35 omega   96.00  122.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -120.0000 26

 36 omega   41.00   96.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 55

 37 omega   89.00  115.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -60.0000 26

 38 omega   71.00   96.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -30.0000 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      -0.0390082000
_diffrn_orient_matrix_UB_12      -0.0225974000
_diffrn_orient_matrix_UB_13      -0.1714388000
_diffrn_orient_matrix_UB_21      0.1923862000
_diffrn_orient_matrix_UB_22      0.0224226000
_diffrn_orient_matrix_UB_23      0.0126939000
_diffrn_orient_matrix_UB_31      0.0438995000
_diffrn_orient_matrix_UB_32      -0.1180236000
_diffrn_orient_matrix_UB_33      0.0351019000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8560
_diffrn_reflns_point_group_measured_fraction_full 0.913
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_theta_full        67.024
_diffrn_reflns_theta_max         67.024
_diffrn_reflns_theta_min         5.036
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.770
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.28972
_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    1.316
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexane/THF'
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.5
_refine_diff_density_max         0.521
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.089
_refine_ls_abs_structure_details
;
 Flack x determined using 1136 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         2889
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0513
_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^)+(0.0903P)^2^+0.2308P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1314
_refine_ls_wR_factor_ref         0.1330
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_full    0.816
_reflns_Friedel_fraction_max     0.816
_reflns_number_gt                2821
_reflns_number_total             2889
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc05266a2.cif
_cod_data_source_block           fxm-xcr-322dj-136k
_cod_original_cell_volume        889.10(5)
_cod_database_code               7120520
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.94
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00N(H00a,H00b), C00O(H00e,H00f), C00P(H00g,H00n)
2.b Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00D(H00D), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K),
 C00L(H00L), C00M(H00M)
2.c Idealised Me refined as rotating group:
 C00Q(H00o,H00p,H00q)
2.d Idealised tetrahedral OH refined as rotating group:
 O001(H001), O002(H002), O003(H003)
;
_olex2_date_sample_data_collection 2017-03-22
_olex2_submission_special_instructions 'No special instructions were received'