Flexible Biphenyl Chromophore as a Circular Dichroism Probe for Assignment of the Absolute Configuration of Carboxylic Acids
Stefano Superchi; Roberto Bisaccia; Daniele Casarini; Alessandro Laurita; Carlo Rosini; Journal of the American Chemical Society 128 (2006) 6893–6902; doi:10.1021/ja058552a

data_4110601
_publ_contact_author_address
;Universita degli Studi della Basilicata
Dipartimento di Chimica
Via N. Sauro n. 85
85100 Potenza
Italy
;
_publ_contact_author_email       rosini@unibas.it
_publ_contact_author_fax         +39(0971)202223
_publ_contact_author_name        'Prof. Carlo Rosini'
_publ_contact_author_phone       +39(0971)202241
_publ_section_title
;
 Flexible Biphenyl Chromophore as a Circular Dichroism Probe for
 Assignment of the Absolute Configuration of Carboxylic Acids
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6893
_journal_page_last               6902
_journal_paper_doi               10.1021/ja058552a
_journal_volume                  128
_journal_year                    2006
_chemical_absolute_configuration syn
_chemical_compound_source        synthesis
_chemical_formula_moiety         'C23 H21 N O'
_chemical_formula_sum            'C23 H21 N O'
_chemical_formula_weight         327.41
_chemical_melting_point          450
_chemical_name_common            '2-Phenylpropionic acid biphenyl amide'
_chemical_name_systematic
(R)-1-(5,7-Dihydro-dibenzo[c,e]azepin-6-yl)-2-phenyl-propan-1-one
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2005-12-16T18:24:54-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90.000(10)
_cell_angle_beta                 90.000(8)
_cell_angle_gamma                90.000(10)
_cell_formula_units_Z            4
_cell_length_a                   8.8552(9)
_cell_length_b                   9.4886(2)
_cell_length_c                   21.266(2)
_cell_measurement_temperature    293(2)
_cell_volume                     1786.8(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_pressure         101.325
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1915
_diffrn_reflns_theta_full        69.93
_diffrn_reflns_theta_max         69.93
_diffrn_reflns_theta_min         1
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.573
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             696
_exptl_crystal_recrystallization_method
'crystalized from diethyl ether/hexane mixture'
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.6(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         1915
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0377
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0587P)^2^+0.0526P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.1023
_reflns_number_gt                1417
_reflns_number_total             1915
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja058552asi20051216_060828.cif
_cod_data_source_block           cad4
_cod_database_code               4110601