Structure, Conformation, Stereodynamics, Dimer Formation, and Absolute Configuration of Axially Chiral Atropisomers of Hindered Biphenyl Carbinols
Daniele Casarini; Lodovico Lunazzi; Michele Mancinelli; Andrea Mazzanti; Carlo Rosini; Journal of Organic Chemistry 72 (2007) 7667–7676; doi:10.1021/jo701481m

data_4024208
_publ_contact_author
;
Dr. Andrea Mazzanti
University of Bologna
Department of Organic Chemistry A.Mangini
Viale Risorgimento 4
40136 Bologna
Italy
;
_publ_contact_author_email       mazzand@ms.fci.unibo.it
_publ_contact_author_fax         '[039]051 209 3654'
_publ_contact_author_phone       '[039]051 209 3633'
_publ_section_title
;
 Structure, Conformation, Stereodynamics, Dimer Formation, and
 Absolute Configuration of Axially Chiral Atropisomers of
 Hindered Biphenyl Carbinols
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7667
_journal_page_last               7676
_journal_paper_doi               10.1021/jo701481m
_journal_volume                  72
_journal_year                    2007
_chemical_formula_moiety         'C18 H22 O2'
_chemical_formula_sum            'C18 H22 O2'
_chemical_formula_weight         270.36
_chemical_name_systematic
; 
 2,2'-(biphenyl-2,2'-diyl)dipropan-2-ol  
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             30/03/2007
_audit_creation_method           SHELXL-97
_audit_update_record             30/06/2007
_cell_angle_alpha                118.0260(10)
_cell_angle_beta                 95.944(2)
_cell_angle_gamma                101.472(2)
_cell_formula_units_Z            2
_cell_length_a                   8.9963(13)
_cell_length_b                   9.9418(14)
_cell_length_c                   10.2139(14)
_cell_measurement_reflns_used    357
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.55
_cell_measurement_theta_min      2.32
_cell_volume                     769.52(19)
_computing_cell_refinement       'Bruker APEX 2 V1.0-27'
_computing_data_collection       'Bruker APEX 2 V1.0-27'
_computing_data_reduction        'Bruker APEX 2 V1.0-27'
_computing_molecular_graphics    'mercury 1.4.1'
_computing_publication_material  'mercury 1.4.1'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX 2'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0156
_diffrn_reflns_av_sigmaI/netI    0.0195
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7332
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.32
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.9926
_exptl_absorpt_correction_T_min  0.9709
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       brick
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2701
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0413
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0719P)^2^+0.1103P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1316
_reflns_number_gt                2296
_reflns_number_total             2701
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo701481m_data1_0824.cif
_cod_data_source_block           p-1
_cod_database_code               4024208