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_4024186
_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         'C26 H38 O2'
_chemical_formula_sum            'C26 H38 O2'
_chemical_formula_weight         382.56
_chemical_name_systematic
; 
3-[2'-(1-Hydroxy-1-isopropyl-2-methyl-propyl)-biphenyl-2-yl]
-2,4-dimethyl-pentan-3-ol 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             18/07/2006
_audit_creation_method           SHELXL-97
_audit_update_record             30/06/2007
_cell_angle_alpha                90.00
_cell_angle_beta                 103.9570(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0332(9)
_cell_length_b                   23.745(2)
_cell_length_c                   11.0309(11)
_cell_measurement_reflns_used    531
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.19
_cell_measurement_theta_min      2.33
_cell_volume                     2296.2(4)
_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_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0204
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            25552
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.72
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.9800
_exptl_absorpt_correction_T_min  0.9479
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.107
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.729
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         5256
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.729
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0484
_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^)+(0.0768P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1639
_refine_ls_wR_factor_ref         0.1699
_reflns_number_gt                4452
_reflns_number_total             5256
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0701481m_data2_0824.cif
_cod_data_source_block           p21n
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4024186