Synthesis, Conformational Stability, and Asymmetric Transformation of Atropisomeric 1,8-Bisphenolnaphthalenes
Marwan W. Ghosn; Christian Wolf; Journal of Organic Chemistry 76 (2011) 3888–3897; doi:10.1021/jo200309g

data_4026296
_publ_section_title
;
 Synthesis, Conformational Stability, and Asymmetric Transformation of
 Atropisomeric 1,8-Bisphenolnaphthalenes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3888
_journal_page_last               3897
_journal_paper_doi               10.1021/jo200309g
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C32 H34 N2 O4'
_chemical_formula_weight         510.61
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.9560(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.340(2)
_cell_length_b                   6.8469(6)
_cell_length_c                   17.6753(16)
_cell_measurement_temperature    100(2)
_cell_volume                     2654.3(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0405
_diffrn_reflns_av_sigmaI/netI    0.0368
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18762
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9941
_exptl_absorpt_correction_T_min  0.9900
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.107
_refine_diff_density_min         -0.549
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         4669
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.1284
_refine_ls_R_factor_gt           0.0987
_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^)+(0.1335P)^2^+6.1196P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2619
_refine_ls_wR_factor_ref         0.2788
_reflns_number_gt                3327
_reflns_number_total             4669
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200309g_si_002.cif
_cod_data_source_block           9
_cod_database_code               4026296