#------------------------------------------------------------------------------
#$Date: 2020-03-06 04:58:33 +0200 (Fri, 06 Mar 2020) $
#$Revision: 249106 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/00/7240059.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_7240059
loop_
_publ_author_name
'Odounga Odounga, Jean-Eudes'
'Báthori, Nikoletta B.'
_publ_section_title
;
 Systematic comparison of racemic and enantiopure multicomponent crystals
 of phenylsuccinic acid---the role of chirality
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE00072H
_journal_year                    2020
_chemical_formula_sum            'C16 H17 N O4'
_chemical_formula_weight         287.30
_chemical_melting_point          408.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yac'
_space_group_name_H-M_alt        'P 1 n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/4
_audit_update_record
;
2020-01-09 deposited with the CCDC.	2020-02-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.82(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.5310(19)
_cell_length_b                   8.3030(17)
_cell_length_c                   9.885(2)
_cell_measurement_reflns_used    2428
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.77
_cell_measurement_theta_min      2.45
_cell_volume                     726.2(3)
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  Bruker
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10213
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.389
_diffrn_reflns_theta_min         2.453
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_description       chunk
_exptl_crystal_F_000             304
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: aniline'
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1218 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         3608
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0392
_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)+(0.0443P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0810
_refine_ls_wR_factor_ref         0.0862
_reflns_Friedel_coverage         0.973
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                3039
_reflns_number_total             3608
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce00072h2.cif
_cod_data_source_block           racpsa-ani
_cod_original_sg_symbol_H-M      'P n'
_cod_database_code               7240059
_shelx_shelxl_version_number     2016/4
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.972
_shelx_estimated_absorpt_t_max   0.996
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5469(2) 0.4384(3) 0.3316(2) 0.0219(5) Uani 1 1 d . . . . .
H1 H 0.623998 0.485024 0.418615 0.026 Uiso 1 1 calc R U . . .
C2 C 0.5565(2) 0.2562(3) 0.3490(3) 0.0232(5) Uani 1 1 d . . . . .
C3 C 0.6162(3) 0.1889(3) 0.4869(3) 0.0335(6) Uani 1 1 d . . . . .
H3 H 0.654506 0.255166 0.568245 0.040 Uiso 1 1 calc R U . . .
C4 C 0.6190(3) 0.0226(4) 0.5043(3) 0.0422(7) Uani 1 1 d . . . . .
H4 H 0.658193 -0.021627 0.597281 0.051 Uiso 1 1 calc R U . . .
C5 C 0.5644(3) -0.0765(3) 0.3851(3) 0.0414(7) Uani 1 1 d . . . . .
H5 H 0.567799 -0.187659 0.397173 0.050 Uiso 1 1 calc R U . . .
C6 C 0.5045(3) -0.0108(3) 0.2474(4) 0.0394(7) Uani 1 1 d . . . . .
H6 H 0.467441 -0.077640 0.166280 0.047 Uiso 1 1 calc R U . . .
H15A H 0.495(3) 0.660(3) 0.729(3) 0.031(7) Uiso 1 1 d . . . . .
H15B H 0.449(3) 0.666(3) 0.862(3) 0.035(7) Uiso 1 1 d . . . . .
H15C H 0.611(3) 0.647(4) 0.891(3) 0.046(9) Uiso 1 1 d . . . . .
H14 H 0.740(4) 0.495(4) 0.138(4) 0.058(10) Uiso 1 1 d . . . . .
C7 C 0.4994(3) 0.1547(3) 0.2299(3) 0.0316(6) Uani 1 1 d . . . . .
H7 H 0.457053 0.198323 0.136794 0.038 Uiso 1 1 calc R U . . .
C8 C 0.3935(3) 0.5010(3) 0.3244(2) 0.0242(5) Uani 1 1 d . . . . .
H8A H 0.373583 0.604700 0.275707 0.029 Uiso 1 1 calc R U . . .
H8B H 0.314828 0.427019 0.267682 0.029 Uiso 1 1 calc R U . . .
C9 C 0.3892(2) 0.5185(3) 0.4752(2) 0.0212(5) Uani 1 1 d . . . . .
O10 O 0.49142(18) 0.5946(2) 0.56826(18) 0.0315(4) Uani 1 1 d . . . . .
O11 O 0.27742(17) 0.4581(2) 0.49702(18) 0.0304(4) Uani 1 1 d . . . . .
C12 C 0.5827(3) 0.4914(3) 0.2014(3) 0.0242(5) Uani 1 1 d . . . . .
O13 O 0.4939(2) 0.5586(2) 0.0957(2) 0.0415(5) Uani 1 1 d . . . . .
O14 O 0.72273(18) 0.4576(2) 0.21765(19) 0.0342(4) Uani 1 1 d . . . . .
N15 N 0.5204(2) 0.6986(2) 0.8334(2) 0.0248(4) Uani 1 1 d . . . . .
C16 C 0.5298(2) 0.8742(3) 0.8428(2) 0.0233(5) Uani 1 1 d . . . . .
C17 C 0.6698(3) 0.9466(3) 0.8990(3) 0.0336(6) Uani 1 1 d . . . . .
H17 H 0.757479 0.884923 0.932428 0.040 Uiso 1 1 calc R U . . .
C18 C 0.6770(3) 1.1124(3) 0.9045(3) 0.0418(7) Uani 1 1 d . . . . .
H18 H 0.770589 1.163127 0.942721 0.050 Uiso 1 1 calc R U . . .
C19 C 0.5472(3) 1.2038(3) 0.8539(3) 0.0432(7) Uani 1 1 d . . . . .
H19 H 0.553236 1.315614 0.856919 0.052 Uiso 1 1 calc R U . . .
C20 C 0.4084(3) 1.1290(3) 0.7988(3) 0.0445(7) Uani 1 1 d . . . . .
H20 H 0.320722 1.190643 0.765175 0.053 Uiso 1 1 calc R U . . .
C21 C 0.3986(3) 0.9630(3) 0.7933(3) 0.0350(6) Uani 1 1 d . . . . .
H21 H 0.304944 0.912241 0.756748 0.042 Uiso 1 1 calc R U . . .
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 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C12 C1 C2 111.24(19) . . ?
C12 C1 C8 112.08(19) . . ?
C2 C1 C8 111.07(19) . . ?
C12 C1 H1 107.4 . . ?
C2 C1 H1 107.4 . . ?
C8 C1 H1 107.4 . . ?
C3 C2 C7 118.6(2) . . ?
C3 C2 C1 119.9(2) . . ?
C7 C2 C1 121.4(2) . . ?
C2 C3 C4 120.3(3) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 120.4(3) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 119.8(3) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C7 119.9(3) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 C2 120.9(2) . . ?
C6 C7 H7 119.5 . . ?
C2 C7 H7 119.5 . . ?
C9 C8 C1 111.27(19) . . ?
C9 C8 H8A 109.4 . . ?
C1 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
C1 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
O10 C9 O11 123.8(2) . . ?
O10 C9 C8 118.6(2) . . ?
O11 C9 C8 117.55(19) . . ?
O13 C12 O14 123.9(2) . . ?
O13 C12 C1 124.2(2) . . ?
O14 C12 C1 111.9(2) . . ?
C12 O14 H14 109(2) . . ?
C16 N15 H15A 111.3(15) . . ?
C16 N15 H15B 109.3(18) . . ?
H15A N15 H15B 108(2) . . ?
C16 N15 H15C 113.1(19) . . ?
H15A N15 H15C 107(2) . . ?
H15B N15 H15C 108(2) . . ?
C21 C16 C17 121.7(2) . . ?
C21 C16 N15 119.1(2) . . ?
C17 C16 N15 119.2(2) . . ?
C16 C17 C18 118.6(2) . . ?
C16 C17 H17 120.7 . . ?
C18 C17 H17 120.7 . . ?
C19 C18 C17 120.7(3) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C20 119.7(3) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C19 C20 C21 120.5(3) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C16 C21 C20 118.8(2) . . ?
C16 C21 H21 120.6 . . ?
C20 C21 H21 120.6 . . ?
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
C1 C12 1.514(3) . ?
C1 C2 1.522(3) . ?
C1 C8 1.528(3) . ?
C1 H1 0.9800 . ?
C2 C3 1.385(3) . ?
C2 C7 1.385(3) . ?
C3 C4 1.390(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.378(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.383(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.513(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 O10 1.237(3) . ?
C9 O11 1.266(3) . ?
C12 O13 1.208(3) . ?
C12 O14 1.314(3) . ?
O14 H14 0.91(4) . ?
N15 C16 1.462(3) . ?
N15 H15A 1.02(3) . ?
N15 H15B 0.87(3) . ?
N15 H15C 0.94(3) . ?
C16 C21 1.376(3) . ?
C16 C17 1.378(3) . ?
C17 C18 1.379(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.377(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.377(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.381(4) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
