#------------------------------------------------------------------------------
#$Date: 2021-12-17 04:59:22 +0200 (Fri, 17 Dec 2021) $
#$Revision: 271493 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/39/2243955.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_2243955
loop_
_publ_author_name
'Halz, Jan Henrik'
'Hentsch, Andreas'
'Wagner, Christoph'
'Merzweiler, Kurt'
_publ_section_title
;
 Synthesis and crystal structures of three Schiff bases derived from
 3-formylacetylacetone and o-, m- and p-aminobenzoic
 acid
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2056989021013050
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          'C13 H13 N O4'
_chemical_formula_moiety         'C13 H13 N O4'
_chemical_formula_sum            'C13 H13 N O4'
_chemical_formula_weight         247.24
_chemical_name_common
;
3-[(3-Carboxyphenylamino)methylidene]pentane-2,4-dione
;
_chemical_name_systematic
;
3-[(2-Acetyl-3-oxobut-1-en-1-yl)amino]benzoic acid
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4880(4)
_cell_length_b                   6.4726(3)
_cell_length_c                   15.2012(5)
_cell_measurement_reflns_used    10416
_cell_measurement_temperature    170
_cell_measurement_theta_max      29.72
_cell_measurement_theta_min      2.68
_cell_volume                     1130.32(8)
_computing_cell_refinement
;
X-Area (Stoe, 2016)
;
_computing_data_collection
;
X-Area (Stoe, 2016)
;
_computing_data_reduction
;
X-Area (Stoe, 2016)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg et al., 2019)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      170
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'Stoe IPDS 2T'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4667
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.994
_diffrn_reflns_theta_min         2.680
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   none
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.073
_exptl_crystal_size_min          0.073
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.246
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         1346
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0440
_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)+(0.0692P)²+0.4804P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1169
_refine_ls_wR_factor_ref         0.1277
_reflns_number_gt                1118
_reflns_number_total             1346
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            wm5628sup1.cif
_cod_data_source_block           2
_cod_database_code               2243955
_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   0.983
_shelx_estimated_absorpt_t_max   0.992
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'
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 0.95570(13) 0.2500 0.53720(10) 0.0312(4) Uani d 1 . .
O O2 1.00391(13) 0.2500 0.26645(10) 0.0337(4) Uani d 1 . .
O O3 0.55070(12) 0.2500 0.80351(10) 0.0272(4) Uani d 1 . .
H H11 0.532(3) 0.2500 0.856(2) 0.060(11) Uiso d 1 . .
O O4 0.35794(13) 0.2500 0.78224(10) 0.0362(5) Uani d 1 . .
N N 0.73322(14) 0.2500 0.50635(11) 0.0204(4) Uani d 1 . .
H H6 0.7858 0.2500 0.5466 0.025 Uiso calc 1 . .
C C1 1.10424(19) 0.2500 0.43063(16) 0.0359(6) Uani d 1 . .
H H1 1.146(3) 0.2500 0.487(2) 0.046(8) Uiso d 1 . .
H H2 1.1236(17) 0.134(3) 0.3925(15) 0.049(6) Uiso d 1 . .
C C2 0.97887(18) 0.2500 0.45735(13) 0.0236(5) Uani d 1 . .
C C3 0.88505(17) 0.2500 0.39425(13) 0.0210(4) Uani d 1 . .
C C4 0.90572(18) 0.2500 0.29799(13) 0.0251(5) Uani d 1 . .
C C5 0.8029(2) 0.2500 0.23691(15) 0.0422(7) Uani d 1 . .
H H3 0.829(3) 0.2500 0.175(3) 0.069(11) Uiso d 1 . .
H H4 0.7490(18) 0.124(4) 0.2474(14) 0.058(6) Uiso d 1 . .
C C6 0.76977(17) 0.2500 0.42287(13) 0.0209(4) Uani d 1 . .
H H5 0.7126 0.2500 0.3796 0.025 Uiso calc 1 . .
C C7 0.61523(17) 0.2500 0.53461(13) 0.0190(4) Uani d 1 . .
C C8 0.59563(16) 0.2500 0.62497(13) 0.0195(4) Uani d 1 . .
H H7 0.6581 0.2500 0.6638 0.023 Uiso calc 1 . .
C C9 0.48160(17) 0.2500 0.65704(13) 0.0206(4) Uani d 1 . .
C C10 0.38808(17) 0.2500 0.59853(14) 0.0225(5) Uani d 1 . .
H H8 0.3121 0.2500 0.6196 0.027 Uiso calc 1 . .
C C11 0.40940(17) 0.2500 0.50868(14) 0.0238(5) Uani d 1 . .
H H9 0.3470 0.2500 0.4697 0.029 Uiso calc 1 . .
C C12 0.52216(18) 0.2500 0.47599(13) 0.0213(4) Uani d 1 . .
H H10 0.5354 0.2500 0.4156 0.026 Uiso calc 1 . .
C C13 0.45603(17) 0.2500 0.75316(14) 0.0232(5) Uani 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
C13 O3 H11 . . 110(2) ?
C6 N H6 . . 117.1 ?
C6 N C7 . . 125.89(17) ?
C7 N H6 . . 117.1 ?
H1 C1 H2 . . 114.2(15) ?
C2 C1 H1 . . 103.3(18) ?
C2 C1 H2 . . 112.4(12) ?
O1 C2 C1 . . 118.12(19) ?
O1 C2 C3 . . 119.29(19) ?
C3 C2 C1 . . 122.58(18) ?
C2 C3 C4 . . 122.45(17) ?
C6 C3 C2 . . 120.15(18) ?
C6 C3 C4 . . 117.40(18) ?
O2 C4 C3 . . 122.24(18) ?
O2 C4 C5 . . 118.81(19) ?
C3 C4 C5 . . 118.94(18) ?
C4 C5 H3 . . 111(2) ?
C4 C5 H4 . . 112.0(12) ?
H3 C5 H4 . . 109.1(17) ?
N C6 C3 . . 126.50(19) ?
N C6 H5 . . 116.8 ?
C3 C6 H5 . . 116.8 ?
C8 C7 N . . 116.89(17) ?
C12 C7 N . . 122.60(18) ?
C12 C7 C8 . . 120.50(18) ?
C7 C8 H7 . . 120.1 ?
C7 C8 C9 . . 119.73(18) ?
C9 C8 H7 . . 120.1 ?
C8 C9 C13 . . 121.79(18) ?
C10 C9 C8 . . 119.96(18) ?
C10 C9 C13 . . 118.25(17) ?
C9 C10 H8 . . 120.3 ?
C11 C10 C9 . . 119.45(18) ?
C11 C10 H8 . . 120.3 ?
C10 C11 H9 . . 119.4 ?
C12 C11 C10 . . 121.16(19) ?
C12 C11 H9 . . 119.4 ?
C7 C12 H10 . . 120.4 ?
C11 C12 C7 . . 119.20(18) ?
C11 C12 H10 . . 120.4 ?
O3 C13 C9 . . 113.76(16) ?
O4 C13 O3 . . 123.45(19) ?
O4 C13 C9 . . 122.79(19) ?
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 C2 . 1.243(3) y
O2 C4 . 1.226(3) y
O3 H11 . 0.83(4) ?
O3 C13 . 1.330(2) ?
O4 C13 . 1.210(2) ?
N H6 . 0.8600 ?
N C6 . 1.337(3) y
N C7 . 1.422(2) ?
C1 H1 . 0.98(3) ?
C1 H2 . 0.97(2) ?
C1 C2 . 1.496(3) y
C2 C3 . 1.443(3) y
C3 C4 . 1.482(3) y
C3 C6 . 1.394(3) y
C4 C5 . 1.503(3) y
C5 H3 . 0.98(4) ?
C5 H4 . 1.03(2) ?
C6 H5 . 0.9300 ?
C7 C8 . 1.392(3) ?
C7 C12 . 1.392(3) ?
C8 H7 . 0.9300 ?
C8 C9 . 1.398(3) ?
C9 C10 . 1.395(3) ?
C9 C13 . 1.490(3) ?
C10 H8 . 0.9300 ?
C10 C11 . 1.388(3) ?
C11 H9 . 0.9300 ?
C11 C12 . 1.387(3) ?
C12 H10 . 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
O3 H11 O1 6_557 0.83(4) 1.84(4) 2.656(2) 166(3)
N H6 O1 . 0.86 1.96 2.598(2) 130.4
C8 H7 O4 6_657 0.93 2.44 3.327(2) 160.2
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
O1 C2 C3 C4 . . . . 180.000000 ?
O1 C2 C3 C6 . . . . 0.000000 ?
N C7 C8 C9 . . . . 180.000000 ?
N C7 C12 C11 . . . . 180.000000 ?
C1 C2 C3 C4 . . . . 0.000000 ?
C1 C2 C3 C6 . . . . 180.000000 ?
C2 C3 C4 O2 . . . . 0.000000 ?
C2 C3 C4 C5 . . . . 180.000000 ?
C2 C3 C6 N . . . . 0.000000 ?
C4 C3 C6 N . . . . 180.000000 ?
C6 N C7 C8 . . . . 180.000000 y
C6 N C7 C12 . . . . 0.0000(10) ?
C6 C3 C4 O2 . . . . 180.000000 y
C6 C3 C4 C5 . . . . 0.000000 ?
C7 N C6 C3 . . . . 180.000000 ?
C7 C8 C9 C10 . . . . 0.0000(10) ?
C7 C8 C9 C13 . . . . 180.000000 ?
C8 C7 C12 C11 . . . . 0.000000 ?
C8 C9 C10 C11 . . . . 0.0000(10) ?
C8 C9 C13 O3 . . . . 0.0000(10) ?
C8 C9 C13 O4 . . . . 180.000000 ?
C9 C10 C11 C12 . . . . 0.0000(10) ?
C10 C9 C13 O3 . . . . 180.000000 ?
C10 C9 C13 O4 . . . . 0.0000(10) ?
C10 C11 C12 C7 . . . . 0.000000 ?
C12 C7 C8 C9 . . . . 0.0000(10) ?
C13 C9 C10 C11 . . . . 180.000000 ?

_cod_database_fobs_code 2243955
