#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/80/1558035.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_1558035
loop_
_publ_author_name
'Yu, MingChao'
'Wang, LinLin'
'Wang, LingYang'
'Wu, ZhiYong'
_publ_section_title
;
 2-(2-Ethoxy-2-oxoacetamido)benzoic acid
;
_journal_coeditor_code           XU4040
_journal_issue                   5
_journal_name_full               IUCrData
_journal_page_first              x200603
_journal_paper_doi               10.1107/S2414314620006033
_journal_volume                  5
_journal_year                    2020
_chemical_formula_iupac          'C11 H11 N O5'
_chemical_formula_moiety         'C11 H11 N O5'
_chemical_formula_sum            'C11 H11 N O5'
_chemical_formula_weight         237.21
_chemical_name_systematic
;
2-(2-Ethoxy-2-oxoacetamido)benzoic acid
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                106.784(7)
_cell_angle_beta                 97.222(7)
_cell_angle_gamma                92.444(8)
_cell_formula_units_Z            2
_cell_length_a                   4.8774(13)
_cell_length_b                   9.470(3)
_cell_length_c                   12.719(3)
_cell_measurement_reflns_used    4983
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.661
_cell_measurement_theta_min      2.382
_cell_volume                     556.1(3)
_computing_cell_refinement
;
SAINT (Bruker, 2002)
;
_computing_data_collection
;
SMART (Bruker, 2002)
;
_computing_data_reduction
;
SAINT (Bruker, 2002)
;
_computing_molecular_graphics
;
XP in SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014/7 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEX area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.668
_diffrn_reflns_theta_min         3.194
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2002)
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_description       plate
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.730
_exptl_crystal_size_mid          0.235
_exptl_crystal_size_min          0.186
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.274
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         2557
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0487
_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)+(0.0728P)²+0.0917P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1264
_refine_ls_wR_factor_ref         0.1375
_reflns_number_gt                2016
_reflns_number_total             2557
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            xu4040sup1.cif
_cod_data_source_block           I
_cod_database_code               1558035
_cod_database_fobs_code          1558035
_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   0.922
_shelx_estimated_absorpt_t_max   0.979
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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 0.2576(3) 0.38020(16) 1.03091(9) 0.0681(4) Uani d 1 . .
O O2 0.0551(2) 0.41447(12) 0.87522(8) 0.0535(3) Uani d 1 . .
O O3 0.2481(3) 0.12887(17) 0.50560(9) 0.0830(5) Uani d 1 . .
O O4 -0.2254(3) 0.38059(15) 0.60001(9) 0.0660(4) Uani d 1 . .
O O5 -0.1328(2) 0.27460(13) 0.42790(8) 0.0557(3) Uani d 1 . .
N N1 0.1791(2) 0.24475(13) 0.68396(9) 0.0422(3) Uani d 1 . .
C C1 0.3864(3) 0.23438(16) 0.86482(11) 0.0420(3) Uani d 1 . .
C C2 0.5692(3) 0.1711(2) 0.92768(13) 0.0551(4) Uani d 1 . .
C C3 0.7340(4) 0.0645(2) 0.87854(15) 0.0602(4) Uani d 1 . .
C C4 0.7185(3) 0.01962(18) 0.76469(14) 0.0533(4) Uani d 1 . .
C C5 0.5376(3) 0.07796(17) 0.70010(12) 0.0463(3) Uani d 1 . .
C C6 0.3673(3) 0.18576(15) 0.74833(10) 0.0385(3) Uani d 1 . .
C C7 0.2187(3) 0.35013(17) 0.92252(11) 0.0456(3) Uani d 1 . .
C C8 0.1306(3) 0.21176(16) 0.57239(10) 0.0451(3) Uani d 1 . .
C C9 -0.1000(3) 0.29967(16) 0.53589(11) 0.0446(3) Uani d 1 . .
C C10 -0.3469(4) 0.3514(2) 0.38191(15) 0.0622(5) Uani d 1 . .
C C11 -0.3098(6) 0.3297(3) 0.26382(17) 0.0828(7) Uani d 1 . .
H H1 0.139(5) 0.455(3) 1.061(2) 0.099(8) Uiso d 1 . .
H H1A 0.065(4) 0.311(2) 0.7222(17) 0.070(6) Uiso d 1 . .
H H2 0.581(4) 0.206(2) 1.0049(19) 0.078(6) Uiso d 1 . .
H H3 0.856(4) 0.025(2) 0.9243(18) 0.081(6) Uiso d 1 . .
H H4 0.836(4) -0.0499(19) 0.7304(16) 0.058(5) Uiso d 1 . .
H H5 0.532(4) 0.046(2) 0.6220(16) 0.054(4) Uiso d 1 . .
H H10A -0.321(4) 0.452(2) 0.4258(18) 0.077(6) Uiso d 1 . .
H H10B -0.517(4) 0.307(2) 0.3905(17) 0.075(6) Uiso d 1 . .
H H11A -0.121(6) 0.375(3) 0.260(2) 0.114(9) Uiso d 1 . .
H H11B -0.326(5) 0.229(3) 0.224(2) 0.109(9) Uiso d 1 . .
H H11C -0.457(5) 0.377(3) 0.230(2) 0.096(7) Uiso d 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 O1 H1 . . 108.9(15) ?
C9 O5 C10 . . 116.37(13) ?
C8 N1 C6 . . 128.24(12) ?
C8 N1 H1A . . 115.5(12) ?
C6 N1 H1A . . 116.1(12) ?
C2 C1 C6 . . 119.03(13) ?
C2 C1 C7 . . 118.80(12) ?
C6 C1 C7 . . 122.16(12) ?
C3 C2 C1 . . 121.37(14) ?
C3 C2 H2 . . 121.1(13) ?
C1 C2 H2 . . 117.5(13) ?
C2 C3 C4 . . 119.29(15) ?
C2 C3 H3 . . 118.4(13) ?
C4 C3 H3 . . 122.3(13) ?
C5 C4 C3 . . 120.89(14) ?
C5 C4 H4 . . 119.0(11) ?
C3 C4 H4 . . 120.1(11) ?
C4 C5 C6 . . 120.72(14) ?
C4 C5 H5 . . 119.4(11) ?
C6 C5 H5 . . 119.9(11) ?
N1 C6 C5 . . 121.55(12) ?
N1 C6 C1 . . 119.77(11) ?
C5 C6 C1 . . 118.68(13) ?
O2 C7 O1 . . 121.64(13) ?
O2 C7 C1 . . 124.02(12) ?
O1 C7 C1 . . 114.35(12) ?
O3 C8 N1 . . 127.84(14) ?
O3 C8 C9 . . 121.08(13) ?
N1 C8 C9 . . 111.06(11) ?
O4 C9 O5 . . 126.54(14) ?
O4 C9 C8 . . 122.79(12) ?
O5 C9 C8 . . 110.66(12) ?
O5 C10 C11 . . 106.64(18) ?
O5 C10 H10A . . 106.7(13) ?
C11 C10 H10A . . 113.3(13) ?
O5 C10 H10B . . 105.1(12) ?
C11 C10 H10B . . 113.6(13) ?
H10A C10 H10B . . 110.7(18) ?
C10 C11 H11A . . 109.9(15) ?
C10 C11 H11B . . 111.3(16) ?
H11A C11 H11B . . 109(2) ?
C10 C11 H11C . . 108.4(15) ?
H11A C11 H11C . . 110(2) ?
H11B C11 H11C . . 108(2) ?
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 C7 . 1.3116(17) ?
O1 H1 . 0.96(3) ?
O2 C7 . 1.2258(17) ?
O3 C8 . 1.2007(18) ?
O4 C9 . 1.1963(18) ?
O5 C9 . 1.3122(16) ?
O5 C10 . 1.456(2) ?
N1 C8 . 1.3493(17) ?
N1 C6 . 1.3944(18) ?
N1 H1A . 0.93(2) ?
C1 C2 . 1.392(2) ?
C1 C6 . 1.4084(18) ?
C1 C7 . 1.474(2) ?
C2 C3 . 1.374(2) ?
C2 H2 . 0.94(2) ?
C3 C4 . 1.377(2) ?
C3 H3 . 0.94(2) ?
C4 C5 . 1.371(2) ?
C4 H4 . 0.939(18) ?
C5 C6 . 1.3955(19) ?
C5 H5 . 0.948(19) ?
C8 C9 . 1.532(2) ?
C10 C11 . 1.491(3) ?
C10 H10A . 0.95(2) ?
C10 H10B . 0.95(2) ?
C11 H11A . 1.01(3) ?
C11 H11B . 0.93(3) ?
C11 H11C . 0.98(3) ?
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
O1 H1 O2 2_567 0.96(3) 1.67(3) 2.6274(16) 176(2) yes
N1 H1A O2 . 0.93(2) 1.92(2) 2.6574(15) 135.1(16) yes
C5 H5 O3 . 0.948(19) 2.230(18) 2.866(2) 123.7(14) yes
C5 H5 O3 2_656 0.948(19) 2.36(2) 3.1107(19) 135.9(14) 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
C6 C1 C2 C3 . . . . 1.2(2) ?
C7 C1 C2 C3 . . . . -178.93(16) ?
C1 C2 C3 C4 . . . . 0.2(3) ?
C2 C3 C4 C5 . . . . -1.2(3) ?
C3 C4 C5 C6 . . . . 0.8(3) ?
C8 N1 C6 C5 . . . . -0.1(2) ?
C8 N1 C6 C1 . . . . -179.63(13) ?
C4 C5 C6 N1 . . . . -178.99(14) ?
C4 C5 C6 C1 . . . . 0.5(2) ?
C2 C1 C6 N1 . . . . 178.03(13) ?
C7 C1 C6 N1 . . . . -1.9(2) ?
C2 C1 C6 C5 . . . . -1.5(2) ?
C7 C1 C6 C5 . . . . 178.62(13) ?
C2 C1 C7 O2 . . . . 178.82(14) ?
C6 C1 C7 O2 . . . . -1.3(2) ?
C2 C1 C7 O1 . . . . -1.2(2) ?
C6 C1 C7 O1 . . . . 178.69(13) ?
C6 N1 C8 O3 . . . . -3.3(3) ?
C6 N1 C8 C9 . . . . 178.43(13) ?
C10 O5 C9 O4 . . . . -1.1(2) ?
C10 O5 C9 C8 . . . . 179.88(14) ?
O3 C8 C9 O4 . . . . 178.26(18) ?
N1 C8 C9 O4 . . . . -3.3(2) ?
O3 C8 C9 O5 . . . . -2.7(2) ?
N1 C8 C9 O5 . . . . 175.70(12) ?
C9 O5 C10 C11 . . . . 169.35(16) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 40082
