Crystal structure and DFT study of the zwitterionic form of 3-{(<i>E</i>)-1-[(4-ethoxyphenyl)iminiumyl]ethyl}-6-methyl-2-oxo-2<i>H</i>-pyran-4-olate
Djedouani, Amel; Anak, Barkahem; Tabti, Salima; Cleymand, Franck; François, Michel; Fleutot, Solenne; Acta Crystallographica Section E 74 (2018) 172–175; doi:10.1107/S2056989018000919

data_2242325
_publ_section_title
;
 Crystal structure and DFT study of the zwitterionic form of
 3-{(<i>E</i>)-1-[(4-ethoxyphenyl)iminiumyl]ethyl}-6-methyl-2-oxo-2<i>H</i>-pyran-4-olate
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              172
_journal_page_last               175
_journal_paper_doi               10.1107/S2056989018000919
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C16 H17 N O4'
_chemical_formula_moiety         'C16 H17 N O4'
_chemical_formula_sum            'C16 H17 N O4'
_chemical_formula_weight         287.30
_chemical_name_systematic
(<i>E</i>)-6-methyl-2-oxo-3-[1-(<i>p</i>-ethoxyiminio)ethyl]-2<i>H</i>-pyran-4-olate
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 105.564(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.0983(13)
_cell_length_b                   7.7792(5)
_cell_length_c                   17.7036(11)
_cell_measurement_reflns_used    18962
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      2.0
_cell_volume                     2799.1(3)
_computing_cell_refinement
;
SAINT (Bruker, 2004)
;
_computing_data_collection
;
APEX2 (Bruker, 2004)
;
_computing_data_reduction
;
SAINT (Bruker, 2004)
;
_computing_molecular_graphics
;
Mercury (Macrae <i>et al.</i>,  2008)
;
_computing_publication_material
;
<i>SHELXL2016/6</i> (Sheldrick, 2015), PLATON (Spek, 2009) and
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
<i>SHELXL2016/6</i> (Sheldrick, 2015)
;
_computing_structure_solution
;
<i>SHELXS2016/6</i> (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII QUAZAR CCD'
_diffrn_measurement_method       'f\ and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         ImuS
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17108
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.989
_diffrn_reflns_theta_min         2.004
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2004)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       plate
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.208
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         2750
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0354
_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^)+(0.0419P)^2^+2.3424P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.0939
_reflns_number_gt                2315
_reflns_number_total             2750
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ex2003sup1.cif
_cod_data_source_block           I
_cod_database_code               2242325
_cod_database_fobs_code          2242325
_shelx_hkl_checksum              16289
_shelx_res_checksum              78969