#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:01:59 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301802 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/87/2108732.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_2108732
loop_
_publ_author_name
'Guillén, Marilia'
'Mora, Asiloé J.'
'Belandria, Lusbely M.'
'Seijas, Luis E.'
'Ramírez, Jeans W.'
'Burgos, José L.'
'Rincón, Luis'
'Delgado, Gerzon E.'
_publ_section_title
;
 Two conformational polymorphs of 4-methylhippuric acid
;
_journal_coeditor_code           AW5049SUP1
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2052520620013773
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C10 H11 N O3'
_chemical_formula_moiety         'C10 H11 N O3'
_chemical_formula_sum            'C10 H11 N O3'
_chemical_formula_weight         193.20
_chemical_melting_point_gt       433
_chemical_melting_point_lt       434
_chemical_name_common            '4-Methylhippuric acid polymorph II'
_chemical_name_systematic        '2-[(4-Methylbenzoyl)amino]ethanoic acid'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                90
_cell_angle_beta                 94.364(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.590(3)
_cell_length_b                   8.670(3)
_cell_length_c                   23.811(7)
_cell_measurement_reflns_used    4019
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.392
_cell_measurement_theta_min      2.501
_cell_volume                     1974.0(11)
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_structure_refinement  'SHELXL2018 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean CCD
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0945
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            46748
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.392
_diffrn_reflns_theta_min         2.501
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Jacobson, 1998)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rectangular plates'
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.314
_exptl_crystal_size_mid          0.309
_exptl_crystal_size_min          0.034
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0079(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL2018 (Sheldrick, 2015)'
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4019
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.1086
_refine_ls_R_factor_gt           0.0486
_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)+(0.0438P)²+0.6696P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1217
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2413
_reflns_number_total             4019
_reflns_threshold_expression     'I > 2σ(I)'
_publcif_datablock.id            {c26a842a-6fda-4f0f-a6c4-4faf18084701}
_publcif_info_exptl_table_max_cols 5
_publcif_info_exptl_table_use_headnotes y
_cod_data_source_file            aw5049sup1.cif
_cod_data_source_block           4MHA-II
_cod_original_cell_volume        1974.1(11)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2108732
_cod_database_fobs_code          2108732
_shelx_shelxl_version_number     2018/1
_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   0.970
_shelx_estimated_absorpt_t_max   0.997
_publcif_funding_html
;
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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_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
O1A O 0.41603(16) 0.55182(18) -0.07757(6) 0.0490(4) Uani 1 1 d . . . . .
H1A H 0.509(3) 0.575(3) -0.0767(12) 0.102(10) Uiso 1 1 d . . . . .
O2A O 0.42402(13) 0.69175(17) 0.00177(6) 0.0489(4) Uani 1 1 d . . . . .
O3A O 0.31008(14) 0.40957(17) 0.06907(6) 0.0525(4) Uani 1 1 d . . . . .
N1A N 0.16422(18) 0.5815(2) 0.02682(7) 0.0436(5) Uani 1 1 d . . . . .
H4A H 0.102(2) 0.651(3) 0.0297(9) 0.055(7) Uiso 1 1 d . . . . .
C1A C 0.3629(2) 0.6070(2) -0.03182(9) 0.0377(5) Uani 1 1 d . . . . .
C2A C 0.2158(2) 0.5504(2) -0.02739(8) 0.0442(5) Uani 1 1 d . . . . .
H2A H 0.154653 0.599489 -0.056412 0.053 Uiso 1 1 calc R U . . .
H3A H 0.212763 0.440045 -0.034180 0.053 Uiso 1 1 calc R U . . .
C3A C 0.21786(19) 0.5081(2) 0.07295(9) 0.0410(5) Uani 1 1 d . . . . .
C4A C 0.16457(19) 0.5458(2) 0.12847(9) 0.0420(5) Uani 1 1 d . . . . .
C5A C 0.2249(2) 0.4715(3) 0.17611(10) 0.0523(6) Uani 1 1 d . . . . .
H5A H 0.294401 0.398418 0.172088 0.063 Uiso 1 1 calc R U . . .
C6A C 0.1842(2) 0.5037(3) 0.22902(10) 0.0596(7) Uani 1 1 d . . . . .
H6A H 0.227498 0.452621 0.259964 0.072 Uiso 1 1 calc R U . . .
C7A C 0.0811(2) 0.6097(3) 0.23724(10) 0.0597(7) Uani 1 1 d . . . . .
C8A C 0.0198(3) 0.6815(3) 0.18972(10) 0.0707(8) Uani 1 1 d . . . . .
H7A H -0.051433 0.752478 0.193813 0.085 Uiso 1 1 calc R U . . .
C9A C 0.0606(2) 0.6517(3) 0.13640(10) 0.0611(7) Uani 1 1 d . . . . .
H8A H 0.017646 0.703549 0.105564 0.073 Uiso 1 1 calc R U . . .
C10A C 0.0392(3) 0.6469(4) 0.29573(10) 0.0859(9) Uani 1 1 d . . . . .
H9A H 0.093283 0.585227 0.322883 0.129 Uiso 1 1 calc R U . . .
H10A H -0.058366 0.624906 0.297821 0.129 Uiso 1 1 calc R U . . .
H11A H 0.056146 0.754149 0.303603 0.129 Uiso 1 1 calc R U . . .
O1B O 0.93657(17) 0.9188(2) -0.07612(6) 0.0606(5) Uani 1 1 d . . . . .
H1B H 1.026(3) 0.906(4) -0.0719(13) 0.114(12) Uiso 1 1 d . . . . .
O2B O 0.93440(13) 0.80226(17) 0.00767(6) 0.0507(4) Uani 1 1 d . . . . .
O3B O 0.78581(13) 1.09458(17) 0.06821(6) 0.0473(4) Uani 1 1 d . . . . .
N1B N 0.66341(17) 0.9100(2) 0.01986(7) 0.0405(4) Uani 1 1 d . . . . .
H4B H 0.597(2) 0.843(2) 0.0197(9) 0.049(6) Uiso 1 1 d . . . . .
C1B C 0.8778(2) 0.8775(2) -0.03010(8) 0.0371(5) Uani 1 1 d . . . . .
C2B C 0.73181(19) 0.9378(2) -0.03122(8) 0.0421(5) Uani 1 1 d . . . . .
H2B H 0.733513 1.048035 -0.038082 0.051 Uiso 1 1 calc R U . . .
H3B H 0.676804 0.890489 -0.062485 0.051 Uiso 1 1 calc R U . . .
C3B C 0.69173(18) 0.9959(2) 0.06611(8) 0.0375(5) Uani 1 1 d . . . . .
C4B C 0.60166(18) 0.9766(2) 0.11392(8) 0.0370(5) Uani 1 1 d . . . . .
C5B C 0.5782(2) 1.1050(3) 0.14675(9) 0.0451(5) Uani 1 1 d . . . . .
H5B H 0.622658 1.197473 0.139600 0.054 Uiso 1 1 calc R U . . .
C6B C 0.4898(2) 1.0975(3) 0.18989(9) 0.0518(6) Uani 1 1 d . . . . .
H6B H 0.474385 1.185933 0.210651 0.062 Uiso 1 1 calc R U . . .
C7B C 0.4242(2) 0.9627(3) 0.20284(9) 0.0534(6) Uani 1 1 d . . . . .
C8B C 0.4499(2) 0.8348(3) 0.17056(10) 0.0610(7) Uani 1 1 d . . . . .
H7B H 0.407618 0.741739 0.178677 0.073 Uiso 1 1 calc R U . . .
C9B C 0.5361(2) 0.8404(3) 0.12659(9) 0.0522(6) Uani 1 1 d . . . . .
H8B H 0.549996 0.752184 0.105495 0.063 Uiso 1 1 calc R U . . .
C10B C 0.3293(3) 0.9573(4) 0.25101(11) 0.0856(9) Uani 1 1 d . . . . .
H9B H 0.385025 0.958497 0.286239 0.128 Uiso 1 1 calc R U . . .
H10B H 0.274303 0.864701 0.248335 0.128 Uiso 1 1 calc R U . . .
H11B H 0.268414 1.045391 0.248896 0.128 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
C3A N1A C2A 120.61(19) . . ?
O2A C1A O1A 124.58(18) . . ?
C1A O1A H1A 109.7(2) . . ?
O2A C1A C2A 124.29(18) . . ?
O1A C1A C2A 111.13(18) . . ?
N1A C2A C1A 112.87(17) . . ?
C2A N1A H4A 119.5(2) . . ?
C3A N1A H4A 119.8(2) . . ?
O3A C3A N1A 119.9(2) . . ?
O3A C3A C4A 120.85(19) . . ?
N1A C3A C4A 119.20(18) . . ?
C9A C4A C5A 117.2(2) . . ?
C9A C4A C3A 124.61(19) . . ?
C5A C4A C3A 118.21(19) . . ?
C6A C5A C4A 121.6(2) . . ?
C7A C6A C5A 121.6(2) . . ?
C6A C7A C8A 116.8(2) . . ?
C6A C7A C10A 121.2(2) . . ?
C8A C7A C10A 122.1(2) . . ?
C9A C8A C7A 122.4(2) . . ?
C4A C9A C8A 120.6(2) . . ?
C1A C2A H2A 109.0 . . ?
N1A C2A H2A 109.0 . . ?
N1A C2A H3A 109.0 . . ?
H2A C2A H3A 108.0 . . ?
C1A C2A H3A 109.0 . . ?
C6A C5A H5A 119.0 . . ?
C4A C5A H5A 119.0 . . ?
C7A C6A H6A 119.0 . . ?
C5A C6A H6A 119.0 . . ?
C9A C8A H7A 119.0 . . ?
C7A C8A H7A 119.0 . . ?
C4A C9A H8A 120.0 . . ?
C8A C9A H8A 120.0 . . ?
C7A C10A H10A 109.0 . . ?
C7A C10A H9A 109.0 . . ?
H9A C10A H11A 109.0 . . ?
H9A C10A H10A 109.0 . . ?
C7A C10A H11A 109.0 . . ?
H10A C10A H11A 109.0 . . ?
C3B N1B C2B 121.50(18) . . ?
O2B C1B O1B 124.74(19) . . ?
C1B O1B H1B 111.0(2) . . ?
O2B C1B C2B 124.81(18) . . ?
O1B C1B C2B 110.45(18) . . ?
N1B C2B C1B 114.32(16) . . ?
C2B N1B H4B 119.4(1) . . ?
C3B N1B H4B 118.8(1) . . ?
O3B C3B N1B 121.14(18) . . ?
O3B C3B C4B 120.57(18) . . ?
N1B C3B C4B 118.19(17) . . ?
C9B C4B C5B 117.79(18) . . ?
C9B C4B C3B 124.24(19) . . ?
C5B C4B C3B 117.94(18) . . ?
C6B C5B C4B 121.1(2) . . ?
C7B C6B C5B 121.6(2) . . ?
C6B C7B C8B 117.0(2) . . ?
C6B C7B C10B 120.4(2) . . ?
C8B C7B C10B 122.5(2) . . ?
C7B C8B C9B 122.3(2) . . ?
C4B C9B C8B 120.2(2) . . ?
N1B C2B H2B 109.0 . . ?
N1B C2B H3B 109.0 . . ?
C1B C2B H2B 109.0 . . ?
C1B C2B H3B 109.0 . . ?
H2B C2B H3B 108.0 . . ?
C4B C5B H5B 120.0 . . ?
C6B C5B H5B 120.0 . . ?
C5B C6B H6B 119.0 . . ?
C7B C6B H6B 119.0 . . ?
C7B C8B H7B 119.0 . . ?
C9B C8B H7B 119.0 . . ?
C4B C9B H8B 120.0 . . ?
C8B C9B H8B 120.0 . . ?
C7B C10B H9B 109.0 . . ?
C7B C10B H10B 109.0 . . ?
C7B C10B H11B 109.0 . . ?
H9B C10B H10B 109.0 . . ?
H9B C10B H11B 109.0 . . ?
H10B C10B H11B 110.0 . . ?
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
O1A C1A 1.326(2) . ?
O2A C1A 1.205(2) . ?
O3A C3A 1.238(2) . ?
N1A C3A 1.338(3) . ?
N1A C2A 1.442(3) . ?
C1A C2A 1.506(3) . ?
C3A C4A 1.490(3) . ?
C4A C9A 1.379(3) . ?
C4A C5A 1.391(3) . ?
C5A C6A 1.376(3) . ?
C6A C7A 1.374(3) . ?
C7A C8A 1.383(3) . ?
C7A C10A 1.514(3) . ?
C8A C9A 1.381(3) . ?
O1A H1A 0.910(3) . ?
N1A H4A 0.850(2) . ?
C2A H2A 0.970 . ?
C2A H3A 0.970 . ?
C5A H5A 0.930 . ?
C6A H6A 0.930 . ?
C8A H7A 0.930 . ?
C9A H8A 0.930 . ?
C10A H9A 0.960 . ?
C10A H10A 0.960 . ?
C10A H11A 0.960 . ?
O1B C1B 1.319(2) . ?
O2B C1B 1.206(2) . ?
O3B C3B 1.241(2) . ?
N1B C3B 1.340(3) . ?
N1B C2B 1.445(2) . ?
C1B C2B 1.493(3) . ?
C3B C4B 1.490(3) . ?
C4B C9B 1.382(3) . ?
C4B C5B 1.388(3) . ?
C5B C6B 1.382(3) . ?
C6B C7B 1.374(3) . ?
C7B C8B 1.381(3) . ?
C7B C10B 1.519(3) . ?
C8B C9B 1.384(3) . ?
O1B H1B 0.860(3) . ?
N1B H4B 0.862(2) . ?
C2B H2B 0.970 . ?
C2B H3B 0.970 . ?
C5B H5B 0.930 . ?
C6B H6B 0.930 . ?
C8B H7B 0.930 . ?
C9B H8B 0.930 . ?
C10B H9B 0.960 . ?
C10B H10B 0.960 . ?
C10B H11B 0.960 . ?
loop_
_publcif_info_cif.paper_type
CB
loop_
_publcif_info_datablock.id
_publcif_info_datablock.publ_exptl
_publcif_info_datablock.publ_geom
_publcif_info_datablock.structure
{1435ed5e-15b8-4ec0-a055-4741481d580f} y y y
{c26a842a-6fda-4f0f-a6c4-4faf18084701} y y y
loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max
loop_
_publcif_info_exptl_table_header_item
Datablock_name
loop_
_publcif_info_tables.block_id
_publcif_info_tables.reference_item
{1435ed5e-15b8-4ec0-a055-4741481d580f} '_publcif_info_datablock.publ_exptl'
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168308543
