##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     'WinGX routine-INITIALISE'
_journal_date_recd_electronic     2006-12-24
_journal_date_accepted     2007-02-05
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      3
_journal_page_first     o1271
_journal_page_last     o1273
_journal_paper_category     EO
_journal_coeditor_code     LN3035
_publ_contact_author_name     'Amel, Djedouani'
_publ_contact_author_address
;
Laboratoire d'Electrochimie des Matériaux Moléculaires et Complexes
Département de Génie des Procédés
Faculté des Science de l'Ingénieur
Université Farhet Abbes de Setif
DZ-19000 Sétif
Algérie
;
_publ_contact_author_email     djedouani_amel@yahoo.fr
_publ_contact_author_fax     '00 (213) 31 61 46 44'
_publ_contact_author_phone     '00 (213) 31 61 46 44'
_publ_section_title
;\
Zwitterionic
(E)-6-methyl-2-oxo-3-[1-(p-tolyliminio)ethyl]-2H-pyran-\
4-olate
;
loop_
    _publ_author_name
    _publ_author_address
    'Djedouani, Amel'
;
Laboratoire d'Electrochimie des Matériaux Moléculaires et Complexes
Département de Génie des Procédés
Faculté des Science de l'Ingénieur
Université Farhet Abbes de Setif
DZ-19000 Sétif
Algeria
;
    'Bendaas, Abderrahmen'
;
Laboratoire d'Electrochimie des Matériaux Moléculaires et Complexes
Département de Génie des Procédés
Faculté des Science de l'Ingénieur
Université Farhet Abbes de Setif
DZ-19000 Sétif
Algeria
;
    'Boufas, Sihem'
;
Faculté des Sciences
Département de Chimie
Université Mentouri de Constantine
Constantine
Algeria
;
    'Allain, Magali'
;
CIMM
CNRS UMR 6200
Faculté des Science
Angers Cedex
France
;
    'Bouet, Gilles'
;
SONAS, EA 921
Université D'Angers
Faculté de Pharmacie
Angers Cedex
France
;
    'Khan, Mustayeen'
;
SONAS, EA 921
Université D'Angers
Faculté de Pharmacie
Angers Cedex
France
;
data_I
_chemical_name_systematic
;
(E)-6-methyl-2-oxo-3-[1-(p-tolyliminio)ethyl]-2H-pyran-4-olate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C15 H15 N1 O3'
_chemical_formula_sum     'C15 H15 N O3'
_chemical_formula_structural     'C15 H15 N1 O3'
_chemical_formula_iupac     'C15 H15 N1 O3'
_chemical_formula_weight     257.28
_symmetry_cell_setting     'monoclinic'
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     14.131(2)
_cell_length_b     7.8128(6)
_cell_length_c     12.841(2)
_cell_angle_alpha     90
_cell_angle_beta     109.92(2)
_cell_angle_gamma     90
_cell_volume     1332.9(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2841
_cell_measurement_theta_min     3.05
_cell_measurement_theta_max     25.8
_cell_measurement_temperature     173(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.35
_exptl_crystal_size_mid     0.05
_exptl_crystal_size_min     0.02
_exptl_crystal_density_diffrn     1.282
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     544
_exptl_absorpt_coefficient_mu     0.09
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
;
_diffrn_ambient_temperature     173(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_measurement_device     'Nonius KappaCCD'
_diffrn_measurement_method     'CCD'
_diffrn_detector_area_resol_mean     9
_diffrn_reflns_number     10079
_diffrn_reflns_av_R_equivalents     0.0399
_diffrn_reflns_av_sigmaI/netI     0.0378
_diffrn_reflns_theta_min     3.02
_diffrn_reflns_theta_max     26.02
_diffrn_reflns_theta_full     26.02
_diffrn_measured_fraction_theta_max     0.985
_diffrn_measured_fraction_theta_full     0.985
_diffrn_reflns_limit_h_min     -16
_diffrn_reflns_limit_h_max     17
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_reflns_number_total     2581
_reflns_number_gt     1487
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_gt     0.0402
_refine_ls_wR_factor_ref     0.1099
_refine_ls_goodness_of_fit_ref     0.884
_refine_ls_restrained_S_all     0.884
_refine_ls_number_reflns     2581
_refine_ls_number_parameters     179
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.0634P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0
_refine_diff_density_max     0.109
_refine_diff_density_min     -0.13
_refine_ls_extinction_method     none
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'COLLECT (Nonius, 1997)'
_computing_cell_refinement     'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction     'SCALEPACK and DENZO (Otwinowski & Minor, 1997)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and MERCURY (Macrae et al.,  2006)'
_computing_publication_material
                             'WinGX (Farrugia, 1999) and PARST (Nardelli, 1995)'
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_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.96325(16) 0.8363(4) 0.6561(2) 0.1078(8) Uani d . 1 . .
    H H1A 1 0.9416 0.6639 0.129 Uiso calc R 1 . .
    H H1B 1.0013 0.7452 0.6393 0.129 Uiso calc R 1 . .
    H H1C 0.9519 0.8111 0.7241 0.129 Uiso calc R 1 . .
    C C2 0.86497(14) 0.8531(3) 0.56502(16) 0.0724(5) Uani d . 1 . .
    C C3 0.77491(13) 0.8298(3) 0.57339(15) 0.0695(5) Uani d . 1 . .
    H H3 0.7704 0.7997 0.6416 0.084 Uiso calc R 1 . .
    C C4 0.68452(13) 0.8498(2) 0.48027(14) 0.0615(4) Uani d . 1 . .
    C C5 0.69439(12) 0.8968(2) 0.37635(13) 0.0551(4) Uani d . 1 . .
    C C6 0.79348(13) 0.9139(3) 0.36927(15) 0.0694(5) Uani d . 1 . .
    C C7 0.60849(12) 0.9238(2) 0.28059(13) 0.0539(4) Uani d . 1 . .
    C C8 0.61333(14) 0.9966(2) 0.17518(14) 0.0664(5) Uani d . 1 . .
    H H8A 0.6652 1.0821 0.1916 0.08 Uiso calc R 1 . .
    H H8B 0.5497 1.0476 0.1341 0.08 Uiso calc R 1 . .
    H H8C 0.6282 0.907 0.132 0.08 Uiso calc R 1 . .
    C C9 0.42279(13) 0.8904(2) 0.20279(13) 0.0574(4) Uani d . 1 . .
    C C10 0.40667(14) 0.8122(2) 0.10152(14) 0.0658(5) Uani d . 1 . .
    H H10 0.4602 0.7638 0.0853 0.079 Uiso calc R 1 . .
    C C11 0.31062(15) 0.8066(3) 0.02479(16) 0.0741(5) Uani d . 1 . .
    H H11 0.3002 0.7546 -0.0434 0.089 Uiso calc R 1 . .
    C C12 0.22964(15) 0.8761(3) 0.04661(17) 0.0767(6) Uani d . 1 . .
    C C13 0.24728(15) 0.9513(3) 0.14907(18) 0.0815(6) Uani d . 1 . .
    H H13 0.1936 0.9977 0.1659 0.098 Uiso calc R 1 . .
    C C14 0.34285(14) 0.9589(3) 0.22681(15) 0.0694(5) Uani d . 1 . .
    H H14 0.3532 1.0102 0.2952 0.083 Uiso calc R 1 . .
    C C15 0.12531(17) 0.8683(4) -0.0396(2) 0.1129(9) Uani d . 1 . .
    H H15A 0.0827 0.9507 -0.0219 0.136 Uiso calc R 1 . .
    H H15B 0.0979 0.7557 -0.0404 0.136 Uiso calc R 1 . .
    H H15C 0.1292 0.8936 -0.1112 0.136 Uiso calc R 1 . .
    N N1 0.51920(10) 0.88972(19) 0.28791(12) 0.0595(4) Uani d . 1 . .
    O O1 0.81620(10) 0.9390(3) 0.28800(11) 0.1035(6) Uani d . 1 . .
    O O2 0.60066(9) 0.8289(2) 0.49350(10) 0.0800(4) Uani d . 1 . .
    O O3 0.87607(9) 0.8939(2) 0.46639(11) 0.0829(4) Uani d . 1 . .
    H H1 0.5251(14) 0.860(2) 0.3600(17) 0.083(6) Uiso d . 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    C1 0.0717(14) 0.136(2) 0.0970(17) -0.0151(14) 0.0053(12) -0.0027(15)
    C2 0.0630(11) 0.0793(14) 0.0700(11) -0.0104(9) 0.0166(9) -0.0065(9)
    C3 0.0620(11) 0.0862(14) 0.0578(10) -0.0068(9) 0.0170(9) 0.0068(9)
    C4 0.0598(10) 0.0651(11) 0.0620(10) -0.0031(8) 0.0239(8) 0.0048(8)
    C5 0.0584(9) 0.0560(10) 0.0559(9) -0.0067(7) 0.0259(8) -0.0064(7)
    C6 0.0632(11) 0.0848(14) 0.0639(10) -0.0191(9) 0.0263(9) -0.0204(9)
    C7 0.0640(10) 0.0476(9) 0.0566(9) -0.0060(7) 0.0289(8) -0.0036(7)
    C8 0.0794(12) 0.0681(12) 0.0603(10) -0.0098(9) 0.0347(9) 0.0001(8)
    C9 0.0605(10) 0.0592(11) 0.0530(9) -0.0006(8) 0.0202(8) 0.0114(7)
    C10 0.0733(11) 0.0664(12) 0.0609(10) -0.0053(9) 0.0268(9) 0.0041(8)
    C11 0.0843(13) 0.0740(13) 0.0589(10) -0.0159(11) 0.0178(10) 0.0090(9)
    C12 0.0717(12) 0.0692(13) 0.0776(13) -0.0067(10) 0.0103(10) 0.0218(10)
    C13 0.0647(12) 0.0807(15) 0.0971(15) 0.0095(10) 0.0248(11) 0.0100(12)
    C14 0.0675(11) 0.0720(13) 0.0707(11) 0.0034(9) 0.0263(9) 0.0024(9)
    C15 0.0803(15) 0.115(2) 0.1129(18) -0.0100(14) -0.0070(13) 0.0238(15)
    N1 0.0600(9) 0.0686(10) 0.0529(8) -0.0009(7) 0.0229(7) 0.0087(7)
    O1 0.0738(9) 0.1776(17) 0.0722(8) -0.0339(10) 0.0419(7) -0.0238(9)
    O2 0.0598(7) 0.1195(12) 0.0647(8) -0.0002(7) 0.0263(6) 0.0259(7)
    O3 0.0602(7) 0.1139(12) 0.0750(9) -0.0193(7) 0.0236(7) -0.0142(8)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    C1 C2 . 1.486(3) ?
    C1 H1A . 0.96 ?
    C1 H1B . 0.96 ?
    C1 H1C . 0.96 ?
    C2 C3 . 1.326(2) ?
    C2 O3 . 1.366(2) ?
    C3 C4 . 1.430(2) ?
    C3 H3 . 0.93 ?
    C4 O2 . 1.2637(19) yes
    C4 C5 . 1.436(2) ?
    C5 C7 . 1.419(2) yes
    C5 C6 . 1.440(2) ?
    C6 O1 . 1.208(2) yes
    C6 O3 . 1.396(2) ?
    C7 N1 . 1.324(2) yes
    C7 C8 . 1.491(2) ?
    C8 H8A . 0.96 ?
    C8 H8B . 0.96 ?
    C8 H8C . 0.96 ?
    C9 C14 . 1.377(2) ?
    C9 C10 . 1.383(2) ?
    C9 N1 . 1.427(2) yes
    C10 C11 . 1.380(3) ?
    C10 H10 . 0.93 ?
    C11 C12 . 1.379(3) ?
    C11 H11 . 0.93 ?
    C12 C13 . 1.384(3) ?
    C12 C15 . 1.513(3) ?
    C13 C14 . 1.380(3) ?
    C13 H13 . 0.93 ?
    C14 H14 . 0.93 ?
    C15 H15A . 0.96 ?
    C15 H15B . 0.96 ?
    C15 H15C . 0.96 ?
    N1 H1 . 0.93(2) ?
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
    C2 C1 H1A . . 109.5 ?
    C2 C1 H1B . . 109.5 ?
    H1A C1 H1B . . 109.5 ?
    C2 C1 H1C . . 109.5 ?
    H1A C1 H1C . . 109.5 ?
    H1B C1 H1C . . 109.5 ?
    C3 C2 O3 . . 121.59(18) ?
    C3 C2 C1 . . 126.1(2) ?
    O3 C2 C1 . . 112.27(18) ?
    C2 C3 C4 . . 121.73(17) ?
    C2 C3 H3 . . 119.1 ?
    C4 C3 H3 . . 119.1 ?
    O2 C4 C3 . . 119.00(15) ?
    O2 C4 C5 . . 123.40(16) ?
    C3 C4 C5 . . 117.59(15) ?
    C7 C5 C4 . . 121.21(14) ?
    C7 C5 C6 . . 119.65(15) ?
    C4 C5 C6 . . 119.13(16) ?
    O1 C6 O3 . . 113.73(15) ?
    O1 C6 C5 . . 128.32(18) ?
    O3 C6 C5 . . 117.91(15) ?
    N1 C7 C5 . . 117.59(14) ?
    N1 C7 C8 . . 118.74(16) ?
    C5 C7 C8 . . 123.59(15) ?
    C7 C8 H8A . . 109.5 ?
    C7 C8 H8B . . 109.5 ?
    H8A C8 H8B . . 109.5 ?
    C7 C8 H8C . . 109.5 ?
    H8A C8 H8C . . 109.5 ?
    H8B C8 H8C . . 109.5 ?
    C14 C9 C10 . . 119.82(17) ?
    C14 C9 N1 . . 118.16(15) ?
    C10 C9 N1 . . 121.80(16) ?
    C11 C10 C9 . . 119.49(18) ?
    C11 C10 H10 . . 120.3 ?
    C9 C10 H10 . . 120.3 ?
    C12 C11 C10 . . 121.66(19) ?
    C12 C11 H11 . . 119.2 ?
    C10 C11 H11 . . 119.2 ?
    C11 C12 C13 . . 117.86(18) ?
    C11 C12 C15 . . 120.3(2) ?
    C13 C12 C15 . . 121.8(2) ?
    C14 C13 C12 . . 121.4(2) ?
    C14 C13 H13 . . 119.3 ?
    C12 C13 H13 . . 119.3 ?
    C9 C14 C13 . . 119.77(18) ?
    C9 C14 H14 . . 120.1 ?
    C13 C14 H14 . . 120.1 ?
    C12 C15 H15A . . 109.5 ?
    C12 C15 H15B . . 109.5 ?
    H15A C15 H15B . . 109.5 ?
    C12 C15 H15C . . 109.5 ?
    H15A C15 H15C . . 109.5 ?
    H15B C15 H15C . . 109.5 ?
    C7 N1 C9 . . 128.99(14) ?
    C7 N1 H1 . . 110.9(12) ?
    C9 N1 H1 . . 120.1(12) ?
    C2 O3 C6 . . 121.95(14) ?
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 O3 C2 C3 . . . . 0.2(3) ?
    C6 O3 C2 C1 . . . . 179.2(2) ?
    O3 C2 C3 C4 . . . . -1.4(3) ?
    C1 C2 C3 C4 . . . . 179.8(2) ?
    C2 C3 C4 O2 . . . . -178.80(19) ?
    C2 C3 C4 C5 . . . . -0.1(3) ?
    O2 C4 C5 C7 . . . . 0.4(3) ?
    C3 C4 C5 C7 . . . . -178.24(17) ?
    O2 C4 C5 C6 . . . . -178.66(18) ?
    C3 C4 C5 C6 . . . . 2.7(3) ?
    C2 O3 C6 O1 . . . . -175.50(19) ?
    C2 O3 C6 C5 . . . . 2.4(3) ?
    C7 C5 C6 O1 . . . . -5.3(3) ?
    C4 C5 C6 O1 . . . . 173.7(2) ?
    C7 C5 C6 O3 . . . . 177.14(16) ?
    C4 C5 C6 O3 . . . . -3.8(3) ?
    C9 N1 C7 C5 . . . . -173.64(16) ?
    C9 N1 C7 C8 . . . . 9.5(3) ?
    C4 C5 C7 N1 . . . . -5.8(2) ?
    C6 C5 C7 N1 . . . . 173.21(16) ?
    C4 C5 C7 C8 . . . . 170.90(16) ?
    C6 C5 C7 C8 . . . . -10.1(2) ?
    C7 N1 C9 C14 . . . . -138.75(18) ?
    C7 N1 C9 C10 . . . . 46.6(3) ?
    C14 C9 C10 C11 . . . . 1.2(3) ?
    N1 C9 C10 C11 . . . . 175.70(16) ?
    C9 C10 C11 C12 . . . . -0.5(3) ?
    C10 C11 C12 C13 . . . . -0.5(3) ?
    C10 C11 C12 C15 . . . . 179.76(19) ?
    C11 C12 C13 C14 . . . . 0.8(3) ?
    C15 C12 C13 C14 . . . . -179.5(2) ?
    C10 C9 C14 C13 . . . . -0.9(3) ?
    N1 C9 C14 C13 . . . . -175.62(17) ?
    C12 C13 C14 C9 . . . . -0.1(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
    N1 H1 O2 1_555 0.93(2) 1.70(2) 2.5396(19) 148.4(19)
    C3 H3 O1 4_576 0.93 2.57 3.354(3) 142
    C8 H8A O1 1_555 0.96 2.35 2.773(3) 106
    C8 H8C O2 4_575 0.96 2.50 3.414(2) 160
