#------------------------------------------------------------------------------
#$Date: 2025-08-21 22:04:39 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301851 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/25/7052535.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_7052535
loop_
_publ_author_name
'Domínguez, Oscar'
'Rodríguez-Molina, Braulio'
'Rodríguez, Mario'
'Ariza, Armando'
'Farfán, Norberto'
'Santillan, Rosa'
_publ_section_title
;
 X-Ray crystallographic and spectroscopic properties of eight Schiff
 bases as evidence of the proton transfer reaction. Role of the
 intermolecular hydrogen bond
;
_journal_issue                   1
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              156
_journal_paper_doi               10.1039/c0nj00179a
_journal_volume                  35
_journal_year                    2011
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C21 H19 N1 O2'
_chemical_formula_sum            'C21 H19 N O2'
_chemical_formula_weight         317.37
_chemical_name_common
(1R,2S)-2-((2-hydroxy-1,2-diphenyl-ethylimino)-methyl)-phenol
_chemical_name_systematic
;
(1R,2S)-2-[(2-hydroxy-1,2-diphenyl-ethylimino)-methyl]-phenol
;
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2010-07-20T23:29:25-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.1478(2)
_cell_length_b                   7.5477(2)
_cell_length_c                   36.07980(10)
_cell_measurement_reflns_used    4678
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.91
_cell_measurement_wavelength     0.71073
_cell_volume                     1674.17(7)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.882
_diffrn_measured_fraction_theta_max 0.869
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      -0.874791E-1
_diffrn_orient_matrix_UB_12      -0.110313
_diffrn_orient_matrix_UB_13      -0.00367
_diffrn_orient_matrix_UB_21      0.133882
_diffrn_orient_matrix_UB_22      -0.732058E-1
_diffrn_orient_matrix_UB_23      0.36398E-2
_diffrn_orient_matrix_UB_31      -0.296861E-1
_diffrn_orient_matrix_UB_32      -0.50825E-2
_diffrn_orient_matrix_UB_33      0.272301E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_unetI/netI     0.0705
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            4795
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.19
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
The light-atom structure prevented a useful absolute structure parameter.
However, the chirality of the molecule is completely reliable by considering
the enantiomeric purity of the starting material,
(1S,2R)-2-amino-1,2-diphenyletanol. The Friedel-pairs reflections were
merged in the refinement by using MERG4, Flack H D (1983), Acta Cryst. A39,
876-881.
;
_refine_ls_abs_structure_Flack   -10(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         1958
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0940
_refine_ls_R_factor_gt           0.0499
_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/[σ²(Fo²)+(0.0841P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1488
_reflns_number_gt                1312
_reflns_number_total             1958
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            C0NJ00179A.TXT
_cod_data_source_block           Compound3
_cod_original_formula_sum        'C21 H19 N1 O2'
_cod_database_code               7052535
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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.4549(5) 0.3070(4) 0.44591(10) 0.0416(8) Uani 1 1 d . . .
C3 C 0.3167(6) 0.3591(5) 0.47426(10) 0.0505(9) Uani 1 1 d . . .
H3 H 0.1815 0.3053 0.4769 0.061 Uiso 1 1 calc R . .
C4 C 0.3787(7) 0.4903(5) 0.49859(12) 0.0558(10) Uani 1 1 d . . .
H4 H 0.2845 0.5251 0.5174 0.067 Uiso 1 1 calc R . .
C5 C 0.5817(7) 0.5716(5) 0.49526(10) 0.0561(10) Uani 1 1 d . . .
H5 H 0.6233 0.6599 0.5118 0.067 Uiso 1 1 calc R . .
C6 C 0.7182(6) 0.5200(4) 0.46754(11) 0.0490(9) Uani 1 1 d . . .
H6 H 0.8528 0.5751 0.4652 0.059 Uiso 1 1 calc R . .
C7 C 0.6610(5) 0.3866(4) 0.44258(9) 0.0382(8) Uani 1 1 d . . .
C8 C 0.8106(6) 0.3271(4) 0.41431(9) 0.0413(8) Uani 1 1 d . . .
H8 H 0.947 0.3798 0.4129 0.05 Uiso 1 1 calc R . .
C10 C 0.9307(5) 0.1397(4) 0.36601(10) 0.0423(8) Uani 1 1 d . . .
H10 H 1.0617 0.2108 0.3702 0.051 Uiso 1 1 calc R . .
C11 C 0.9878(5) -0.0550(5) 0.37569(9) 0.0436(8) Uani 1 1 d . . .
H11 H 1.1155 -0.0895 0.3611 0.052 Uiso 1 1 calc R . .
C12 C 0.8654(6) 0.1649(4) 0.32547(9) 0.0402(8) Uani 1 1 d . . .
C13 C 1.0150(6) 0.2339(5) 0.30074(11) 0.0523(9) Uani 1 1 d . . .
H13 H 1.154 0.2619 0.3091 0.063 Uiso 1 1 calc R . .
C14 C 0.9630(7) 0.2620(6) 0.26408(11) 0.0607(11) Uani 1 1 d . . .
H14 H 1.0656 0.3098 0.248 0.073 Uiso 1 1 calc R . .
C15 C 0.7564(8) 0.2189(6) 0.25117(11) 0.0597(11) Uani 1 1 d . . .
H15 H 0.7197 0.2377 0.2265 0.072 Uiso 1 1 calc R . .
C16 C 0.6068(7) 0.1479(5) 0.27546(12) 0.0572(10) Uani 1 1 d . . .
H16 H 0.4693 0.1167 0.2669 0.069 Uiso 1 1 calc R . .
C17 C 0.6593(6) 0.1223(5) 0.31254(11) 0.0496(9) Uani 1 1 d . . .
H18 H 0.5559 0.0764 0.3287 0.06 Uiso 1 1 calc R . .
C18 C 0.8081(6) -0.1849(4) 0.36770(9) 0.0439(8) Uani 1 1 d . . .
C19 C 0.8145(7) -0.2866(5) 0.33568(11) 0.0592(11) Uani 1 1 d . . .
H19 H 0.9339 -0.2793 0.3199 0.071 Uiso 1 1 calc R . .
C20 C 0.6434(10) -0.3993(5) 0.32712(13) 0.0754(14) Uani 1 1 d . . .
H20 H 0.648 -0.4657 0.3054 0.091 Uiso 1 1 calc R . .
C21 C 0.4671(8) -0.4137(5) 0.35038(15) 0.0721(13) Uani 1 1 d . . .
H21 H 0.3514 -0.4874 0.3442 0.086 Uiso 1 1 calc R . .
C22 C 0.4635(7) -0.3176(5) 0.38298(13) 0.0601(11) Uani 1 1 d . . .
H22 H 0.3465 -0.329 0.3991 0.072 Uiso 1 1 calc R . .
C23 C 0.6328(6) -0.2046(4) 0.39166(10) 0.0475(9) Uani 1 1 d . . .
H23 H 0.6294 -0.1412 0.4137 0.057 Uiso 1 1 calc R . .
N9 N 0.7635(4) 0.2051(3) 0.39114(8) 0.0404(7) Uani 1 1 d . . .
O1 O 0.3911(4) 0.1794(3) 0.42197(7) 0.0571(7) Uani 1 1 d D . .
O2 O 1.0422(4) -0.0695(3) 0.41394(8) 0.0558(7) Uani 1 1 d . . .
H1 H 0.502(5) 0.149(5) 0.4081(10) 0.067 Uiso 1 1 d D . .
H2 H 1.147(7) -0.002(5) 0.4160(13) 0.067 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 0.0033 0 '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 0.0061 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C2 C3 119.7(3) . . ?
O1 C2 C7 120.7(3) . . ?
C3 C2 C7 119.6(3) . . ?
C4 C3 C2 120.3(4) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.6(4) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 119.2(4) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C7 121.7(4) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C6 C7 C2 118.6(3) . . ?
C6 C7 C8 121.3(3) . . ?
C2 C7 C8 120.0(3) . . ?
N9 C8 C7 122.8(3) . . ?
N9 C8 H8 118.6 . . ?
C7 C8 H8 118.6 . . ?
N9 C10 C12 111.6(3) . . ?
N9 C10 C11 109.9(3) . . ?
C12 C10 C11 113.1(3) . . ?
N9 C10 H10 107.3 . . ?
C12 C10 H10 107.3 . . ?
C11 C10 H10 107.3 . . ?
O2 C11 C18 107.9(3) . . ?
O2 C11 C10 110.1(3) . . ?
C18 C11 C10 114.1(3) . . ?
O2 C11 H11 108.2 . . ?
C18 C11 H11 108.2 . . ?
C10 C11 H11 108.2 . . ?
C13 C12 C17 118.5(4) . . ?
C13 C12 C10 119.3(3) . . ?
C17 C12 C10 122.2(3) . . ?
C14 C13 C12 121.5(4) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C13 C14 C15 119.8(4) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C16 C15 C14 119.1(4) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C15 C16 C17 120.8(4) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C12 C17 C16 120.2(4) . . ?
C12 C17 H18 119.9 . . ?
C16 C17 H18 119.9 . . ?
C19 C18 C23 118.7(4) . . ?
C19 C18 C11 119.9(3) . . ?
C23 C18 C11 121.3(3) . . ?
C20 C19 C18 120.2(4) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C21 C20 C19 120.7(4) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C21 C22 119.4(4) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 H21 120.3 . . ?
C23 C22 C21 120.3(4) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C18 120.6(3) . . ?
C22 C23 H23 119.7 . . ?
C18 C23 H23 119.7 . . ?
C8 N9 C10 119.5(3) . . ?
C2 O1 H1 109(3) . . ?
C11 O2 H2 103(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2 O1 1.352(4) . ?
C2 C3 1.386(5) . ?
C2 C7 1.408(5) . ?
C3 C4 1.377(5) . ?
C3 H3 0.93 . ?
C4 C5 1.396(5) . ?
C4 H4 0.93 . ?
C5 C6 1.362(5) . ?
C5 H5 0.93 . ?
C6 C7 1.396(5) . ?
C6 H6 0.93 . ?
C7 C8 1.445(4) . ?
C8 N9 1.276(4) . ?
C8 H8 0.93 . ?
C10 N9 1.457(4) . ?
C10 C12 1.529(5) . ?
C10 C11 1.551(5) . ?
C10 H10 0.98 . ?
C11 O2 1.424(4) . ?
C11 C18 1.505(5) . ?
C11 H11 0.98 . ?
C12 C13 1.384(5) . ?
C12 C17 1.388(5) . ?
C13 C14 1.377(5) . ?
C13 H13 0.93 . ?
C14 C15 1.391(6) . ?
C14 H14 0.93 . ?
C15 C16 1.379(6) . ?
C15 H15 0.93 . ?
C16 C17 1.390(5) . ?
C16 H16 0.93 . ?
C17 H18 0.93 . ?
C18 C19 1.388(5) . ?
C18 C23 1.390(5) . ?
C19 C20 1.387(6) . ?
C19 H19 0.93 . ?
C20 C21 1.375(7) . ?
C20 H20 0.93 . ?
C21 C22 1.382(6) . ?
C21 H21 0.93 . ?
C22 C23 1.381(5) . ?
C22 H22 0.93 . ?
C23 H23 0.93 . ?
O1 H1 0.88(2) . ?
O2 H2 0.83(4) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N9 0.88(2) 1.77(3) 2.553(4) 147(4) .
O2 H2 O1 0.83(4) 2.04(4) 2.866(3) 176(4) 1_655
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 -179.3(3) . . . . ?
C7 C2 C3 C4 1.3(5) . . . . ?
C2 C3 C4 C5 -0.5(6) . . . . ?
C3 C4 C5 C6 0.2(6) . . . . ?
C4 C5 C6 C7 -0.7(6) . . . . ?
C5 C6 C7 C2 1.4(5) . . . . ?
C5 C6 C7 C8 -177.1(3) . . . . ?
O1 C2 C7 C6 178.9(3) . . . . ?
C3 C2 C7 C6 -1.7(5) . . . . ?
O1 C2 C7 C8 -2.6(5) . . . . ?
C3 C2 C7 C8 176.9(3) . . . . ?
C6 C7 C8 N9 179.8(3) . . . . ?
C2 C7 C8 N9 1.3(5) . . . . ?
N9 C10 C11 O2 -53.2(4) . . . . ?
C12 C10 C11 O2 -178.7(3) . . . . ?
N9 C10 C11 C18 68.3(4) . . . . ?
C12 C10 C11 C18 -57.2(4) . . . . ?
N9 C10 C12 C13 134.0(3) . . . . ?
C11 C10 C12 C13 -101.4(4) . . . . ?
N9 C10 C12 C17 -45.4(4) . . . . ?
C11 C10 C12 C17 79.2(4) . . . . ?
C17 C12 C13 C14 0.6(5) . . . . ?
C10 C12 C13 C14 -178.8(3) . . . . ?
C12 C13 C14 C15 -0.7(6) . . . . ?
C13 C14 C15 C16 -0.2(6) . . . . ?
C14 C15 C16 C17 1.1(6) . . . . ?
C13 C12 C17 C16 0.4(5) . . . . ?
C10 C12 C17 C16 179.8(3) . . . . ?
C15 C16 C17 C12 -1.3(6) . . . . ?
O2 C11 C18 C19 -137.1(3) . . . . ?
C10 C11 C18 C19 100.2(4) . . . . ?
O2 C11 C18 C23 43.6(4) . . . . ?
C10 C11 C18 C23 -79.2(4) . . . . ?
C23 C18 C19 C20 3.0(5) . . . . ?
C11 C18 C19 C20 -176.3(3) . . . . ?
C18 C19 C20 C21 -0.9(6) . . . . ?
C19 C20 C21 C22 -1.4(6) . . . . ?
C20 C21 C22 C23 1.7(6) . . . . ?
C21 C22 C23 C18 0.5(5) . . . . ?
C19 C18 C23 C22 -2.8(5) . . . . ?
C11 C18 C23 C22 176.6(3) . . . . ?
C7 C8 N9 C10 -173.6(3) . . . . ?
C12 C10 N9 C8 -120.9(3) . . . . ?
C11 C10 N9 C8 112.8(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652934
2 PubChem 135750853
