#------------------------------------------------------------------------------
#$Date: 2016-03-22 10:36:45 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178877 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/06/4110601.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4110601
loop_
_publ_author_name
'Stefano Superchi'
'Roberto Bisaccia'
'Daniele Casarini'
'Alessandro Laurita'
'Carlo Rosini'
_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/[σ²(Fo²)+(0.0587P)²+0.0526P] where P=(Fo²+2Fc²)/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
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
O1 O 0.1544(2) 0.0908(2) 0.24054(9) 0.0578(5) Uani 1 1 d
C17 C -0.2009(3) 0.0092(3) 0.20336(11) 0.0429(6) Uani 1 1 d
N1 N 0.0293(2) -0.0197(2) 0.31767(9) 0.0421(5) Uani 1 1 d
C15 C 0.0521(3) 0.0095(3) 0.25617(12) 0.0412(6) Uani 1 1 d
C2 C -0.1915(3) 0.0055(3) 0.38712(11) 0.0437(6) Uani 1 1 d
C14 C 0.1272(3) 0.0507(3) 0.36398(14) 0.0500(7) Uani 1 1 d
C18 C -0.2151(4) 0.1539(3) 0.20524(15) 0.0528(7) Uani 1 1 d
C22 C -0.3317(4) -0.0703(4) 0.19779(14) 0.0551(8) Uani 1 1 d
C7 C -0.1362(3) 0.0344(3) 0.44724(12) 0.0455(6) Uani 1 1 d
C8 C 0.0113(3) -0.0239(3) 0.46758(12) 0.0464(6) Uani 1 1 d
C1 C -0.1049(3) -0.0908(3) 0.34390(12) 0.0412(6) Uani 1 1 d
C13 C 0.1352(3) -0.0229(3) 0.42634(12) 0.0454(6) Uani 1 1 d
C19 C -0.3556(4) 0.2185(4) 0.20306(17) 0.0655(9) Uani 1 1 d
C16 C -0.0480(3) -0.0609(3) 0.20694(12) 0.0432(6) Uani 1 1 d
C21 C -0.4729(4) -0.0052(4) 0.19546(15) 0.0643(9) Uani 1 1 d
C3 C -0.3273(3) 0.0642(4) 0.36802(14) 0.0553(8) Uani 1 1 d
C10 C 0.1665(5) -0.1343(5) 0.54674(17) 0.0738(10) Uani 1 1 d
C9 C 0.0291(4) -0.0806(4) 0.52775(14) 0.0617(8) Uani 1 1 d
C20 C -0.4833(4) 0.1383(4) 0.19872(15) 0.0647(9) Uani 1 1 d
C12 C 0.2716(4) -0.0795(4) 0.44700(16) 0.0619(9) Uani 1 1 d
C6 C -0.2204(4) 0.1202(4) 0.48730(15) 0.0610(8) Uani 1 1 d
C5 C -0.3547(4) 0.1784(4) 0.46765(18) 0.0731(10) Uani 1 1 d
C4 C -0.4078(4) 0.1512(4) 0.40792(17) 0.0685(9) Uani 1 1 d
C11 C 0.2869(5) -0.1353(4) 0.50655(17) 0.0749(11) Uani 1 1 d
C23 C 0.0318(4) -0.0594(4) 0.14287(16) 0.0598(8) Uiso 1 1 d
H18 H -0.324(4) -0.172(4) 0.1979(15) 0.067(10) Uiso 1 1 d
H12 H 0.088(4) 0.156(4) 0.3708(16) 0.073(10) Uiso 1 1 d
H2 H -0.072(4) -0.177(3) 0.3672(14) 0.057(9) Uiso 1 1 d
H1 H -0.164(3) -0.123(3) 0.3092(13) 0.046(7) Uiso 1 1 d
H11 H 0.233(4) 0.058(3) 0.3438(15) 0.062(9) Uiso 1 1 d
H4 H -0.507(4) 0.177(4) 0.3924(18) 0.089(12) Uiso 1 1 d
H14 H -0.123(3) 0.207(3) 0.2101(15) 0.057(9) Uiso 1 1 d
H15 H -0.364(4) 0.322(4) 0.2048(17) 0.082(11) Uiso 1 1 d
H17 H -0.569(4) -0.068(4) 0.1919(17) 0.078(11) Uiso 1 1 d
H13 H -0.065(3) -0.155(3) 0.2199(14) 0.057(9) Uiso 1 1 d
H16 H -0.584(4) 0.183(4) 0.1983(16) 0.067(10) Uiso 1 1 d
H3 H -0.365(3) 0.048(3) 0.3259(15) 0.060(9) Uiso 1 1 d
H7 H -0.060(4) -0.073(4) 0.5569(17) 0.074(11) Uiso 1 1 d
H10 H 0.351(4) -0.082(3) 0.4198(16) 0.064(10) Uiso 1 1 d
H6 H -0.188(4) 0.144(3) 0.5276(15) 0.063(9) Uiso 1 1 d
H9 H 0.387(5) -0.173(4) 0.5199(17) 0.088(12) Uiso 1 1 d
H8 H 0.177(5) -0.162(4) 0.5896(19) 0.100(13) Uiso 1 1 d
H5 H -0.413(5) 0.225(5) 0.498(2) 0.101(13) Uiso 1 1 d
H19 H -0.041(4) -0.097(4) 0.1131(16) 0.073(10) Uiso 1 1 d
H20 H 0.048(4) 0.028(3) 0.1313(14) 0.064(9) Uiso 1 1 d
H21 H 0.129(4) -0.115(3) 0.1479(15) 0.064(9) Uiso 1 1 d
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C18 C17 C22 117.9(3)
C18 C17 C16 121.3(3)
C22 C17 C16 120.9(3)
C15 N1 C14 117.7(2)
C15 N1 C1 125.4(2)
C14 N1 C1 115.4(2)
O1 C15 N1 119.9(2)
O1 C15 C16 121.0(2)
N1 C15 C16 119.1(2)
C3 C2 C7 119.6(3)
C3 C2 C1 120.4(2)
C7 C2 C1 120.0(2)
N1 C14 C13 114.1(2)
C17 C18 C19 121.4(3)
C17 C22 C21 120.7(3)
C6 C7 C2 119.1(3)
C6 C7 C8 120.7(3)
C2 C7 C8 120.2(2)
C9 C8 C13 119.1(3)
C9 C8 C7 120.7(3)
C13 C8 C7 120.2(2)
N1 C1 C2 111.3(2)
C12 C13 C8 118.5(3)
C12 C13 C14 119.9(3)
C8 C13 C14 121.2(3)
C20 C19 C18 119.9(3)
C17 C16 C15 111.3(2)
C17 C16 C23 111.3(2)
C15 C16 C23 109.7(2)
C20 C21 C22 120.0(3)
C4 C3 C2 120.5(3)
C11 C10 C9 120.5(3)
C10 C9 C8 120.6(3)
C19 C20 C21 120.2(3)
C11 C12 C13 121.5(3)
C5 C6 C7 120.7(3)
C6 C5 C4 119.9(3)
C5 C4 C3 120.1(3)
C10 C11 C12 119.6(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C15 1.235(3)
C17 C18 1.379(4)
C17 C22 1.388(4)
C17 C16 1.510(4)
N1 C15 1.352(3)
N1 C14 1.472(4)
N1 C1 1.476(3)
C15 C16 1.526(4)
C2 C3 1.387(4)
C2 C7 1.397(4)
C2 C1 1.505(4)
C14 C13 1.500(4)
C18 C19 1.388(5)
C22 C21 1.396(5)
C7 C6 1.394(4)
C7 C8 1.483(4)
C8 C9 1.397(4)
C8 C13 1.404(4)
C13 C12 1.393(4)
C19 C20 1.366(5)
C16 C23 1.535(4)
C21 C20 1.366(5)
C3 C4 1.382(5)
C10 C11 1.367(6)
C10 C9 1.380(5)
C12 C11 1.379(5)
C6 C5 1.376(5)
C5 C4 1.379(5)
