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_7120521
_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 unk
_chemical_formula_moiety         'C51 H80 Co N4 O6, 2(Cl O4)'
_chemical_formula_sum            'C51 H80 Cl2 Co N4 O14'
_chemical_formula_weight         1103.02
_chemical_name_systematic        'L-RaPr2/Co(ClO4)2?6H2O complex'
_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     dual
_audit_block_doi                 10.5517/ccdc.csd.cc1p26nm
_audit_creation_date             2017-04-20
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2017-05-20 deposited with the CCDC.
2017-08-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.375(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.6288(8)
_cell_length_b                   16.6036(7)
_cell_length_c                   13.9577(8)
_cell_measurement_reflns_used    7066
_cell_measurement_temperature    143.00(10)
_cell_measurement_theta_max      24.1090
_cell_measurement_theta_min      3.2540
_cell_volume                     2926.6(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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      N~2~
_diffrn_ambient_temperature      143.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     -8.00  20.00   1.00    7.50    --  -14.97 -99.00  90.00   28
  2  \w    -79.00  -8.00   1.00    7.50    --  -14.97 -57.00-150.00   71
  3  \w    -39.00  22.00   1.00    7.50    --   16.84 -57.00  90.00   61
  4  \w    -72.00   8.00   1.00    7.50    --  -14.81 -77.00 120.00   80
  5  \w    -50.00  13.00   1.00    7.50    --   16.53 -57.00-180.00   63
  6  \w      3.00  55.00   1.00    7.50    --   16.53 -99.00 -30.00   52
  7  \w    -21.00   8.00   1.00    7.50    --   16.53 -99.00 -90.00   29
  8  \w     12.00  55.00   1.00    7.50    --   16.53 -99.00   0.00   43
  9  \w     22.00  57.00   1.00    7.50    --   16.53-101.00  37.07   35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0458576000
_diffrn_orient_matrix_UB_12      0.0037294000
_diffrn_orient_matrix_UB_13      -0.0293271000
_diffrn_orient_matrix_UB_21      -0.0322604000
_diffrn_orient_matrix_UB_22      -0.0010089000
_diffrn_orient_matrix_UB_23      0.0413652000
_diffrn_orient_matrix_UB_31      0.0032157000
_diffrn_orient_matrix_UB_32      0.0425425000
_diffrn_orient_matrix_UB_33      0.0035006000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0576
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            28110
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.936
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.447
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74568
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_description       block
_exptl_crystal_F_000             1174
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexane/THF'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.938
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 2871 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.020(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     639
_refine_ls_number_reflns         11959
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.0991
_refine_ls_R_factor_gt           0.0698
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1236P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1768
_refine_ls_wR_factor_ref         0.1959
_reflns_Friedel_coverage         0.929
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                8292
_reflns_number_total             11959
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc05266a2.cif
_cod_data_source_block           1
_cod_database_code               7120521
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C191
_shelx_estimated_absorpt_t_max   0.897
_shelx_estimated_absorpt_t_min   0.859
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl2-O14
 1.5 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C23) = Uanis(C22) = Uanis(C49) = Uanis(C50)
4.a Ternary CH refined with riding coordinates:
 C1(H1), C5(H5), C7(H7), C15(H15), C18(H18), C25(H25), C29(H29), C31(H31),
 C42(H42), C45(H45)
4.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C6(H6A,H6B), C21(H21A,H21B), C22(H22A,
 H22B), C23(H23A,H23B), C24(H24A,H24B), C26(H26A,H26B), C27(H27A,H27B),
 C28(H28A,H28B), C30(H30A,H30B), C33(H33A,H33B), C34(H34A,H34B), C35(H35A,H35B),
  C48(H48A,H48B), C49(H49A,H49B), C50(H50A,H50B), C51(H51A,H51B)
4.c Aromatic/amide H refined with riding coordinates:
 N2(H2), N4(H4), C11(H11), C12(H12), C13(H13), C38(H38), C39(H39), C40(H40)
4.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C43(H43A,H43B,H43C), C44(H44A,H44B,H44C), C46(H46A,H46B,H46C), C47(H47A,
 H47B,H47C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.366
_oxdiff_exptl_absorpt_empirical_full_min 0.743