Stereodynamics and Conformational Chirality of the Atropisomers of Ditolyl Anthrones and Anthraquinone
Lodovico Lunazzi; Michele Mancinelli; Andrea Mazzanti; Journal of Organic Chemistry 73 (2008) 5354–5359; doi:10.1021/jo800677n

data_4023551
_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
;
 Stereodynamics and Conformational Chirality of the Atropisomers
 of Ditolyl Anthrones and Anthraquinone
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5354
_journal_page_last               5359
_journal_paper_doi               10.1021/jo800677n
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C28 H22.3 N0.54 O'
_chemical_formula_weight         382.34
_chemical_name_common            'compound 1'
_chemical_name_systematic
; 
 4,5-dio-tolylanthracen-9(10H)-one 
;
_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             05/03/2008
_audit_creation_method           SHELXL-97
_audit_update_record             19/03/2008
_cell_angle_alpha                71.664(2)
_cell_angle_beta                 76.411(2)
_cell_angle_gamma                72.426(2)
_cell_formula_units_Z            2
_cell_length_a                   7.5933(10)
_cell_length_b                   10.1784(13)
_cell_length_c                   15.0517(19)
_cell_measurement_reflns_used    221
_cell_measurement_temperature    296(2)
_cell_volume                     1040.0(2)
_computing_cell_refinement       'Bruker APEX v2.1.4'
_computing_data_collection       'Bruker APEX v2.1.4'
_computing_data_reduction        Sadabs
_computing_molecular_graphics    'Mercury 1.4.1'
_computing_publication_material  'ortep 32'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.909
_diffrn_measured_fraction_theta_max 0.909
_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  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12113
_diffrn_reflns_theta_full        28.64
_diffrn_reflns_theta_max         28.64
_diffrn_reflns_theta_min         1.44
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9922
_exptl_absorpt_correction_T_min  0.9845
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            'slightly yellow'
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4876
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0606
_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^)+(0.1029P)^2^+0.1627P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1818
_refine_ls_wR_factor_ref         0.2009
_reflns_number_gt                3384
_reflns_number_total             4876
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo800677n-File003.cif
_cod_data_source_block           antrone
_cod_database_code               4023551