#------------------------------------------------------------------------------
#$Date: 2020-07-08 08:12:08 +0300 (Wed, 08 Jul 2020) $
#$Revision: 254112 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/34/2243477.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_2243477
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_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                 99.800(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.3496(6)
_cell_length_b                   5.2632(2)
_cell_length_c                   14.2969(10)
_cell_measurement_reflns_used    15127
_cell_measurement_temperature    295.0(10)
_cell_measurement_theta_max      24.30
_cell_measurement_theta_min      2.74
_cell_volume                     619.12(7)
_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 0.996
_diffrn_measured_fraction_theta_max 0.997
_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  0.0370
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14738
_diffrn_reflns_theta_full        19.664
_diffrn_reflns_theta_max         20.998
_diffrn_reflns_theta_min         2.740
_diffrn_source                   'Sealed X-ray tube'
_diffrn_source_current           0.600
_diffrn_source_power             0.039
_diffrn_source_voltage           65
_exptl_absorpt_coefficient_mu    0.049
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(X-AREA; Stoe & Cie, 2019)
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_description       Prism
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.186
_exptl_crystal_size_min          0.143
_refine_diff_density_max         0.116
_refine_diff_density_min         -0.138
_refine_ls_extinction_coef       0.076(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   0.942
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     159
_refine_ls_number_reflns         2456
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.942
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0355
_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)+(0.0529P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.0899
_reflns_number_gt                1847
_reflns_number_total             2456
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yk2134sup1.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2243477
_shelx_estimated_absorpt_t_min   0.984
_shelx_estimated_absorpt_t_max   0.993
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 0.4368(2) 0.7962(3) 0.72214(11) 0.0587(5) Uani d 1 . .
N N1 0.4801(2) 0.3812(3) 0.75328(12) 0.0469(5) Uani d 1 . .
H H1 0.463(3) 0.230(5) 0.7361(17) 0.056 Uiso d 1 . .
C C1 0.5445(4) 0.2070(5) 0.91253(17) 0.0634(7) Uani d 1 . .
H H1A 0.431636 0.203287 0.918240 0.095 Uiso calc 1 . .
H H1B 0.609341 0.231415 0.974081 0.095 Uiso calc 1 . .
H H1C 0.573648 0.049095 0.886292 0.095 Uiso calc 1 . .
C C2 0.5745(3) 0.4245(4) 0.84752(14) 0.0477(5) Uani d 1 . .
H H2 0.533500 0.580228 0.872634 0.057 Uiso calc 1 . .
C C3 0.7537(3) 0.4647(4) 0.84452(15) 0.0513(5) Uani d 1 . .
C C4 0.8339(4) 0.3259(8) 0.7885(2) 0.0915(10) Uani d 1 . .
H H4 0.777746 0.203331 0.749040 0.110 Uiso calc 1 . .
C C5 0.9981(4) 0.3612(11) 0.7883(2) 0.1148(15) Uani d 1 . .
H H5 1.050709 0.260491 0.749457 0.138 Uiso calc 1 . .
C C6 1.0820(4) 0.5382(9) 0.8431(2) 0.0947(11) Uani d 1 . .
H H6 1.191933 0.563011 0.841941 0.114 Uiso calc 1 . .
C C7 1.0040(4) 0.6813(8) 0.9005(4) 0.1196(15) Uani d 1 . .
H H7 1.060842 0.805082 0.939071 0.144 Uiso calc 1 . .
C C8 0.8399(4) 0.6433(6) 0.9018(3) 0.0898(10) Uani d 1 . .
H H8 0.787916 0.740396 0.941994 0.108 Uiso calc 1 . .
C C9 0.4209(2) 0.5733(4) 0.69593(14) 0.0417(5) Uani d 1 . .
C C10 0.3338(2) 0.5054(4) 0.59924(14) 0.0395(5) Uani d 1 . .
C C11 0.2133(3) 0.6681(4) 0.55550(16) 0.0487(5) Uani d 1 . .
H H11 0.186538 0.811620 0.587523 0.058 Uiso calc 1 . .
C C12 0.1325(3) 0.6186(5) 0.46458(17) 0.0572(6) Uani d 1 . .
H H12 0.050761 0.727543 0.436194 0.069 Uiso calc 1 . .
C C13 0.1725(3) 0.4090(5) 0.41606(16) 0.0528(6) Uani d 1 . .
H H13 0.118548 0.376985 0.354762 0.063 Uiso calc 1 . .
C C14 0.2928(3) 0.2463(4) 0.45841(15) 0.0501(6) Uani d 1 . .
H H14 0.320498 0.105115 0.425418 0.060 Uiso calc 1 . .
C C15 0.3725(3) 0.2925(4) 0.54998(14) 0.0463(5) Uani d 1 . .
H H15 0.452280 0.180724 0.578634 0.056 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 3 8 0.0710
-1 -3 -9 0.0720
1 2 -3 0.1500
-2 -3 6 0.1900
5 -1 0 0.0800
-6 1 1 0.1060
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 . . 122.11(18) ?
C9 N1 H1 . . 120.7(17) ?
C2 N1 H1 . . 117.1(17) ?
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 . . 112.09(17) ?
N1 C2 C1 . . 109.10(18) ?
C3 C2 C1 . . 112.80(19) ?
N1 C2 H2 . . 107.5 ?
C3 C2 H2 . . 107.5 ?
C1 C2 H2 . . 107.5 ?
C4 C3 C8 . . 117.7(3) ?
C4 C3 C2 . . 122.3(2) ?
C8 C3 C2 . . 119.9(2) ?
C3 C4 C5 . . 121.5(3) ?
C3 C4 H4 . . 119.2 ?
C5 C4 H4 . . 119.2 ?
C6 C5 C4 . . 120.8(4) ?
C6 C5 H5 . . 119.6 ?
C4 C5 H5 . . 119.6 ?
C5 C6 C7 . . 118.9(3) ?
C5 C6 H6 . . 120.6 ?
C7 C6 H6 . . 120.6 ?
C6 C7 C8 . . 120.3(3) ?
C6 C7 H7 . . 119.9 ?
C8 C7 H7 . . 119.9 ?
C3 C8 C7 . . 120.7(3) ?
C3 C8 H8 . . 119.6 ?
C7 C8 H8 . . 119.6 ?
O1 C9 N1 . . 121.50(19) ?
O1 C9 C10 . . 121.34(18) ?
N1 C9 C10 . . 117.16(17) ?
C11 C10 C15 . . 118.86(19) ?
C11 C10 C9 . . 118.16(18) ?
C15 C10 C9 . . 122.93(18) ?
C12 C11 C10 . . 120.5(2) ?
C12 C11 H11 . . 119.7 ?
C10 C11 H11 . . 119.7 ?
C13 C12 C11 . . 120.3(2) ?
C13 C12 H12 . . 119.9 ?
C11 C12 H12 . . 119.9 ?
C12 C13 C14 . . 119.9(2) ?
C12 C13 H13 . . 120.1 ?
C14 C13 H13 . . 120.1 ?
C13 C14 C15 . . 120.2(2) ?
C13 C14 H14 . . 119.9 ?
C15 C14 H14 . . 119.9 ?
C14 C15 C10 . . 120.3(2) ?
C14 C15 H15 . . 119.8 ?
C10 C15 H15 . . 119.8 ?
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 . 1.232(3) ?
N1 C9 . 1.342(3) ?
N1 C2 . 1.459(3) ?
N1 H1 . 0.84(3) ?
C1 C2 . 1.522(3) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 C3 . 1.519(3) ?
C2 H2 . 0.9800 ?
C3 C4 . 1.343(4) ?
C3 C8 . 1.368(3) ?
C4 C5 . 1.385(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.336(5) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.359(5) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.388(5) ?
C7 H7 . 0.9300 ?
C8 H8 . 0.9300 ?
C9 C10 . 1.492(3) ?
C10 C11 . 1.387(3) ?
C10 C15 . 1.390(3) ?
C11 C12 . 1.383(3) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.374(4) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.379(3) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.386(3) ?
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_545 0.84(3) 2.30(3) 3.123(2) 168(2) 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 . . . . -85.6(2) ?
C9 N1 C2 C1 . . . . 148.7(2) ?
N1 C2 C3 C4 . . . . -41.1(3) ?
C1 C2 C3 C4 . . . . 82.5(3) ?
N1 C2 C3 C8 . . . . 140.4(2) ?
C1 C2 C3 C8 . . . . -95.9(3) ?
C8 C3 C4 C5 . . . . 0.0(5) ?
C2 C3 C4 C5 . . . . -178.5(3) ?
C3 C4 C5 C6 . . . . -1.0(6) ?
C4 C5 C6 C7 . . . . 1.0(7) ?
C5 C6 C7 C8 . . . . 0.0(6) ?
C4 C3 C8 C7 . . . . 1.0(5) ?
C2 C3 C8 C7 . . . . 179.5(3) ?
C6 C7 C8 C3 . . . . -1.0(6) ?
C2 N1 C9 O1 . . . . -3.7(3) ?
C2 N1 C9 C10 . . . . 176.80(18) ?
O1 C9 C10 C11 . . . . -28.1(3) ?
N1 C9 C10 C11 . . . . 151.43(19) ?
O1 C9 C10 C15 . . . . 149.3(2) ?
N1 C9 C10 C15 . . . . -31.2(3) ?
C15 C10 C11 C12 . . . . 0.3(3) ?
C9 C10 C11 C12 . . . . 177.8(2) ?
C10 C11 C12 C13 . . . . -0.9(4) ?
C11 C12 C13 C14 . . . . 0.5(3) ?
C12 C13 C14 C15 . . . . 0.5(3) ?
C13 C14 C15 C10 . . . . -1.1(3) ?
C11 C10 C15 C14 . . . . 0.7(3) ?
C9 C10 C15 C14 . . . . -176.71(19) ?

_cod_database_fobs_code 2243477
