Synthesis and crystal structures of three Schiff bases derived from 3-formylacetylacetone and <i>o</i>-, <i>m</i>- and <i>p</i>-aminobenzoic acid
Halz, Jan Henrik; Hentsch, Andreas; Wagner, Christoph; Merzweiler, Kurt; Acta Crystallographica Section E 78 (2022) –; doi:10.1107/S2056989021013050

data_2243955
_publ_section_title
;
 Synthesis and crystal structures of three Schiff bases derived from
 3-formylacetylacetone and <i>o</i>-, <i>m</i>- and <i>p</i>-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
;
<i>OLEX2</i> (Dolomanov <i>et al.</i>,  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, \w 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/[\s^2^(Fo^2^)+(0.0692P)^2^+0.4804P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(I)'
_cod_data_source_file            wm5628sup1.cif
_cod_data_source_block           2
_cod_database_code               2243955
_shelx_estimated_absorpt_t_min   0.983
_shelx_estimated_absorpt_t_max   0.992
_shelx_hkl_checksum              72480
_shelx_res_checksum              79907
_cod_database_fobs_code 2243955