#------------------------------------------------------------------------------
#$Date: 2020-07-08 08:12:08 +0300 (Wed, 08 Jul 2020) $
#$Revision: 254112 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/34/2243476.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2243476
loop_
_publ_author_name
'Flores Manuel, Fermin'
'Sosa Rivadeneyra, Martha'
'Bernès, Sylvain'
_publ_section_title
;
 One molecule, three crystal structures: conformational trimorphism of
 N-[(1S)-1-phenylethyl]benzamide
;
_journal_coeditor_code           YK2134
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1229
_journal_page_last               1233
_journal_paper_doi               10.1107/S2056989020008877
_journal_volume                  76
_journal_year                    2020
_chemical_absolute_configuration syn
_chemical_formula_iupac          'C15 H15 N O'
_chemical_formula_moiety         'C15 H15 N O'
_chemical_formula_sum            'C15 H15 N O'
_chemical_formula_weight         225.28
_chemical_melting_point          395
_chemical_name_systematic
;
N-[(1S)-1-Phenylethyl]benzamide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 99.708(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.0472(4)
_cell_length_b                   9.3118(7)
_cell_length_c                   13.9581(15)
_cell_measurement_reflns_used    7505
_cell_measurement_temperature    295.0(10)
_cell_measurement_theta_max      21.00
_cell_measurement_theta_min      2.90
_cell_volume                     646.62(10)
_computing_cell_refinement
;
X-AREA (Stoe & Cie, 2019)
;
_computing_data_collection
;
X-AREA (Stoe & Cie, 2019)
;
_computing_data_reduction
;
X-RED32 (Stoe & Cie, 2019)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2020)
;
_computing_publication_material
;
publCif (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2018/2 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      295.0(10)
_diffrn_detector                 'Reverse-biased silicon diode array'
_diffrn_detector_area_resol_mean 5.81
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Eulerian four-circle diffractometer'
_diffrn_measurement_device_type  'Stoe Stadivari'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support Mitegen
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56083
_diffrn_reflns_av_R_equivalents  0.0662
_diffrn_reflns_av_unetI/netI     0.0584
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15392
_diffrn_reflns_theta_full        19.664
_diffrn_reflns_theta_max         20.999
_diffrn_reflns_theta_min         2.905
_diffrn_source                   'Sealed X-ray tube'
_diffrn_source_current           0.600
_diffrn_source_power             0.039
_diffrn_source_voltage           65
_exptl_absorpt_coefficient_mu    0.047
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.3125
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(X-AREA; Stoe & Cie, 2019)
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.157
_exptl_crystal_description       Prism
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.368
_exptl_crystal_size_mid          0.119
_exptl_crystal_size_min          0.087
_refine_diff_density_max         0.111
_refine_diff_density_min         -0.123
_refine_ls_extinction_coef       0.110(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL-2018/3 (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   0.836
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     159
_refine_ls_number_reflns         2833
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.836
_refine_ls_R_factor_all          0.0857
_refine_ls_R_factor_gt           0.0429
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0482P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.1021
_reflns_number_gt                1573
_reflns_number_total             2833
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yk2134sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2243476
_shelx_estimated_absorpt_t_min   0.983
_shelx_estimated_absorpt_t_max   0.996
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.0514(3) 0.4480(2) 0.20994(15) 0.0634(7) Uani d 1 . .
N N1 0.4967(5) 0.4138(3) 0.24782(19) 0.0552(7) Uani d 1 . .
H H1 0.648(6) 0.434(4) 0.232(2) 0.066 Uiso d 1 . .
C C1 0.5907(9) 0.1568(5) 0.2590(3) 0.0930(13) Uani d 1 . .
H H1A 0.775962 0.172744 0.254262 0.140 Uiso calc 1 . .
H H1B 0.488542 0.143158 0.195139 0.140 Uiso calc 1 . .
H H1C 0.575931 0.072839 0.297644 0.140 Uiso calc 1 . .
C C2 0.4818(6) 0.2871(4) 0.3067(2) 0.0644(10) Uani d 1 . .
H H2 0.291287 0.268881 0.308304 0.077 Uiso calc 1 . .
C C3 0.6215(6) 0.3062(4) 0.4109(2) 0.0607(9) Uani d 1 . .
C C4 0.8300(8) 0.3981(5) 0.4371(3) 0.0897(13) Uani d 1 . .
H H4 0.889422 0.454313 0.389872 0.108 Uiso calc 1 . .
C C5 0.9556(10) 0.4096(7) 0.5331(3) 0.1221(18) Uani d 1 . .
H H5 1.099463 0.472265 0.549813 0.147 Uiso calc 1 . .
C C6 0.8674(14) 0.3286(9) 0.6029(4) 0.125(2) Uani d 1 . .
H H6 0.946930 0.337460 0.667740 0.150 Uiso calc 1 . .
C C7 0.6669(16) 0.2373(8) 0.5769(4) 0.143(2) Uani d 1 . .
H H7 0.609507 0.180178 0.624109 0.171 Uiso calc 1 . .
C C8 0.5405(10) 0.2247(6) 0.4809(3) 0.1114(17) Uani d 1 . .
H H8 0.399651 0.160002 0.464684 0.134 Uiso calc 1 . .
C C9 0.2809(5) 0.4846(3) 0.20237(19) 0.0465(7) Uani d 1 . .
C C10 0.3311(5) 0.6101(3) 0.1421(2) 0.0476(8) Uani d 1 . .
C C11 0.1515(6) 0.6394(4) 0.0594(2) 0.0674(10) Uani d 1 . .
H H11 0.000363 0.581618 0.042805 0.081 Uiso calc 1 . .
C C12 0.1920(9) 0.7537(5) 0.0002(3) 0.0898(14) Uani d 1 . .
H H12 0.072176 0.770246 -0.057018 0.108 Uiso calc 1 . .
C C13 0.4068(10) 0.8418(5) 0.0258(4) 0.0922(15) Uani d 1 . .
H H13 0.431123 0.920152 -0.013150 0.111 Uiso calc 1 . .
C C14 0.5853(8) 0.8160(4) 0.1077(4) 0.0855(13) Uani d 1 . .
H H14 0.731981 0.876693 0.124659 0.103 Uiso calc 1 . .
C C15 0.5512(6) 0.6993(4) 0.1667(3) 0.0646(10) Uani d 1 . .
H H15 0.675967 0.681326 0.222472 0.078 Uiso calc 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0015 0.0009 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -2 -2 0.0640
-1 2 2 0.0550
1 2 -1 0.2070
-1 -2 1 0.1610
-1 2 -9 0.0520
1 -1 6 0.0350
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9 N1 C2 . . 123.7(2) ?
C9 N1 H1 . . 118(2) ?
C2 N1 H1 . . 118(2) ?
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
N1 C2 C3 . . 112.9(3) ?
N1 C2 C1 . . 110.0(3) ?
C3 C2 C1 . . 111.6(3) ?
N1 C2 H2 . . 107.4 ?
C3 C2 H2 . . 107.4 ?
C1 C2 H2 . . 107.4 ?
C8 C3 C4 . . 118.3(4) ?
C8 C3 C2 . . 118.6(4) ?
C4 C3 C2 . . 123.1(3) ?
C3 C4 C5 . . 121.1(4) ?
C3 C4 H4 . . 119.5 ?
C5 C4 H4 . . 119.5 ?
C6 C5 C4 . . 119.8(6) ?
C6 C5 H5 . . 120.1 ?
C4 C5 H5 . . 120.1 ?
C7 C6 C5 . . 119.0(5) ?
C7 C6 H6 . . 120.5 ?
C5 C6 H6 . . 120.5 ?
C6 C7 C8 . . 121.6(5) ?
C6 C7 H7 . . 119.2 ?
C8 C7 H7 . . 119.2 ?
C3 C8 C7 . . 120.2(5) ?
C3 C8 H8 . . 119.9 ?
C7 C8 H8 . . 119.9 ?
O1 C9 N1 . . 121.7(3) ?
O1 C9 C10 . . 121.3(3) ?
N1 C9 C10 . . 116.9(2) ?
C11 C10 C15 . . 118.7(3) ?
C11 C10 C9 . . 118.8(3) ?
C15 C10 C9 . . 122.6(3) ?
C10 C11 C12 . . 120.8(4) ?
C10 C11 H11 . . 119.6 ?
C12 C11 H11 . . 119.6 ?
C13 C12 C11 . . 120.0(4) ?
C13 C12 H12 . . 120.0 ?
C11 C12 H12 . . 120.0 ?
C14 C13 C12 . . 120.2(4) ?
C14 C13 H13 . . 119.9 ?
C12 C13 H13 . . 119.9 ?
C13 C14 C15 . . 120.5(4) ?
C13 C14 H14 . . 119.7 ?
C15 C14 H14 . . 119.7 ?
C10 C15 C14 . . 119.7(3) ?
C10 C15 H15 . . 120.1 ?
C14 C15 H15 . . 120.1 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C9 . 1.229(3) ?
N1 C9 . 1.338(3) ?
N1 C2 . 1.448(4) ?
N1 H1 . 0.85(3) ?
C1 C2 . 1.530(5) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 C3 . 1.515(5) ?
C2 H2 . 0.9800 ?
C3 C8 . 1.354(5) ?
C3 C4 . 1.358(5) ?
C4 C5 . 1.386(5) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.365(8) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.325(8) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.388(8) ?
C7 H7 . 0.9300 ?
C8 H8 . 0.9300 ?
C9 C10 . 1.486(4) ?
C10 C11 . 1.370(4) ?
C10 C15 . 1.383(4) ?
C11 C12 . 1.384(5) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.358(6) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.352(6) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.392(5) ?
C14 H14 . 0.9300 ?
C15 H15 . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 O1 1_655 0.85(3) 2.11(3) 2.952(3) 169(3) yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9 N1 C2 C3 . . . . -120.7(3) ?
C9 N1 C2 C1 . . . . 114.0(3) ?
N1 C2 C3 C8 . . . . 154.8(3) ?
C1 C2 C3 C8 . . . . -80.7(4) ?
N1 C2 C3 C4 . . . . -27.3(5) ?
C1 C2 C3 C4 . . . . 97.1(4) ?
C8 C3 C4 C5 . . . . -0.6(6) ?
C2 C3 C4 C5 . . . . -178.5(4) ?
C3 C4 C5 C6 . . . . -0.7(8) ?
C4 C5 C6 C7 . . . . 1.8(9) ?
C5 C6 C7 C8 . . . . -1.6(10) ?
C4 C3 C8 C7 . . . . 0.8(7) ?
C2 C3 C8 C7 . . . . 178.8(5) ?
C6 C7 C8 C3 . . . . 0.3(9) ?
C2 N1 C9 O1 . . . . 2.0(5) ?
C2 N1 C9 C10 . . . . -178.1(3) ?
O1 C9 C10 C11 . . . . -33.8(4) ?
N1 C9 C10 C11 . . . . 146.2(3) ?
O1 C9 C10 C15 . . . . 145.7(3) ?
N1 C9 C10 C15 . . . . -34.2(4) ?
C15 C10 C11 C12 . . . . 1.5(5) ?
C9 C10 C11 C12 . . . . -179.0(3) ?
C10 C11 C12 C13 . . . . -2.4(6) ?
C11 C12 C13 C14 . . . . 1.7(6) ?
C12 C13 C14 C15 . . . . -0.1(6) ?
C11 C10 C15 C14 . . . . 0.2(4) ?
C9 C10 C15 C14 . . . . -179.4(3) ?
C13 C14 C15 C10 . . . . -0.9(5) ?

_cod_database_fobs_code 2243476
