Copper-catalyzed enantioselective synthesis of bridged bicyclic ketals from 1,1-disubstituted-4-methylene-1,6-hexanediols and related alkenols.
Burde, Ameya S.; Karyakarte, Shuklendu D.; Sylvester, Eric D.; Chemler, Sherry R.; Chemical communications (Cambridge, England) 57 (2021) 105–108; doi:10.1039/d0cc06404a

data_7127519
_publ_section_title
;
 Copper-catalyzed enantioselective synthesis of bridged bicyclic ketals
 from 1,1-disubstituted-4-methylene-1,6-hexanediols and related alkenols.
;
_journal_issue                   1
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              105
_journal_page_last               108
_journal_paper_doi               10.1039/d0cc06404a
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C31 H28 O2'
_chemical_formula_sum            'C31 H28 O2'
_chemical_formula_weight         432.53
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-07-31
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_audit_update_record
;
2020-07-31 deposited with the CCDC.	2020-12-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.826(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.015(2)
_cell_length_b                   9.4761(9)
_cell_length_c                   17.0238(18)
_cell_measurement_reflns_used    6747
_cell_measurement_temperature    90
_cell_measurement_theta_max      26.398
_cell_measurement_theta_min      2.405
_cell_volume                     2249.2(5)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL n/a (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      90.0
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1985
_diffrn_reflns_av_unetI/netI     0.1030
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            21398
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.403
_diffrn_reflns_theta_min         1.795
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7058
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/2 (Bruker,2014/2) was used for absorption correction. wR2(int) was 0.1751 before and 0.0450 after correction. The Ratio of minimum to maximum transmission is 0.9469. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_description       plate
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4604
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0593
_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^)+(0.0181P)^2^+1.2055P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1589
_refine_ls_wR_factor_ref         0.1662
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3661
_reflns_number_total             4604
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc06404a2.cif
_cod_data_source_block           asb-achiralketal-biphenyl
_cod_depositor_comments
'Adding full bibliography for 7127518--7127519.cif.'
_cod_database_code               7127519
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.999
_shelx_estimated_absorpt_t_min   0.997
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid bond restraints
 C6B, C6
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C6B \\sim C5B \\sim C5 \\sim C6: within 1.7A with sigma of 0.02 and sigma for
terminal atoms of 0.08 within 1.7A
Uanis(C6B) = Uanis(C6)
Uanis(C2) = Uanis(C2B)
Uanis(O2) = Uanis(O2B)
Uanis(C6B) = Uanis(C2B) = Uanis(C3B) = Uanis(C5B)
Uanis(C6B) = Uanis(C5B) = Uanis(C2B) = Uanis(C3B)
4. Others
 Sof(O1B)=Sof(O2B)=Sof(C2B)=Sof(H2BA)=Sof(H2BB)=Sof(C3B)=Sof(H3BA)=Sof(H3BB)=
 Sof(C6B)=Sof(H7BA)=Sof(H7BB)=Sof(C5B)=Sof(H8BA)=Sof(H8BB)=1-FVAR(1)
 Sof(O1)=Sof(O2)=Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(C3)=Sof(H3A)=Sof(H3B)=Sof(C5)=
 Sof(H5A)=Sof(H5B)=Sof(C6)=Sof(H6A)=Sof(H6B)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C2B(H2BA,H2BB), C3B(H3BA,H3BB), C6B(H7BA,H7BB), C5B(H8BA,H8BB),
 C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B)
5.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C13(H13), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19), C21(H21), C22(H22), C24(H24), C25(H25), C27(H27), C28(H28), C29(H29),
  C30(H30), C31(H31)
;
_shelx_res_checksum              83697
_shelx_hkl_checksum              12729
_olex2_submission_special_instructions 'No special instructions were received'