N-Heterocyclic carbene promoted enantioselective desymmetrization reaction of diarylalkane-bisphenols
Li, Shoulei; Liu, Bin; Chen, Li; Li, Xin; Cheng, Jin-Pei; Organic Chemistry Frontiers 5 (2018) 1101–; doi:10.1039/C7QO01083D

data_1553964
_publ_section_title
;
 N-Heterocyclic carbene promoted enantioselective desymmetrization
 reaction of diarylalkane-bisphenols
;
_journal_issue                   7
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1101
_journal_paper_doi               10.1039/C7QO01083D
_journal_volume                  5
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H27 Br O3'
_chemical_formula_sum            'C26 H27 Br O3'
_chemical_formula_weight         467.38
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-09-05
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-09-14 deposited with the CCDC.
2018-01-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.839(4)
_cell_length_b                   17.596(4)
_cell_length_c                   8.652(2)
_cell_measurement_reflns_used    7046
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4661
_cell_measurement_theta_min      2.3149
_cell_volume                     2259.1(10)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            15380
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.458
_diffrn_reflns_theta_min         2.745
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    1.844
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.72002
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.323
_exptl_crystal_size_mid          0.261
_exptl_crystal_size_min          0.112
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 1521 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.005(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         5155
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0480
_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^)+(0.0162P)^2^+0.8236P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0846
_refine_ls_wR_factor_ref         0.0877
_reflns_Friedel_coverage         0.762
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                4673
_reflns_number_total             5155
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo01083d2.cif
_cod_data_source_block           a
_cod_original_cell_volume        2259.2(9)
_cod_database_code               1553964
_shelx_estimated_absorpt_t_max   0.820
_shelx_estimated_absorpt_t_min   0.587
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C15(H15), C16(H16), C18(H18), C23(H23), C24(H24),
 C25(H25), C26(H26)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,
 H12C), C19(H19A,H19B,H19C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              1281
_shelx_shelxl_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'