Arylbiphenylene Atropisomers: Structure, Conformation, Stereodynamics, and Absolute Configuration
Lodovico Lunazzi; Michele Mancinelli; Andrea Mazzanti; Journal of Organic Chemistry 73 (2008) 2198–2205; doi:10.1021/jo702502n

data_4023339
_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
;
 Arylbiphenylene Atropisomers: Structure, Conformation,
 Stereodynamics, and Absolute Configuration
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2198
_journal_page_last               2205
_journal_paper_doi               10.1021/jo702502n
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C32 H32'
_chemical_formula_weight         416.58
_chemical_name_common            'compound 4'
_chemical_name_systematic
; 
 1,8-bis(2-tert-butylphenyl)biphenylene  
;
_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             29/05/2007
_audit_creation_method           SHELXL-97
_audit_update_record             10/11/2007
_cell_angle_alpha                90.00
_cell_angle_beta                 95.982(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.132(6)
_cell_length_b                   11.507(6)
_cell_length_c                   21.320(12)
_cell_measurement_temperature    273(2)
_cell_volume                     2472(2)
_computing_cell_refinement       'Bruker APEX v1.0.27'
_computing_data_collection       'Bruker APEX v1.0.27'
_computing_data_reduction        'Bruker APEX 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 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX2'
_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  0.0303
_diffrn_reflns_av_sigmaI/netI    0.0258
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            27469
_diffrn_reflns_theta_full        27.77
_diffrn_reflns_theta_max         27.77
_diffrn_reflns_theta_min         1.92
_exptl_absorpt_coefficient_mu    0.063
_exptl_absorpt_correction_T_max  0.9938
_exptl_absorpt_correction_T_min  0.9814
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.119
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.029
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         5731
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0518
_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^)+(0.0618P)^2^+0.4145P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1278
_refine_ls_wR_factor_ref         0.1464
_reflns_number_gt                3781
_reflns_number_total             5731
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702502n-File004.cif
_cod_data_source_block           bifetbu
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4023339