#------------------------------------------------------------------------------
#$Date: 2018-01-17 08:40:45 +0200 (Wed, 17 Jan 2018) $
#$Revision: 205326 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/23/2242325.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_2242325
loop_
_publ_author_name
'Djedouani, Amel'
'Anak, Barkahem'
'Tabti, Salima'
'Cleymand, Franck'
'François, Michel'
'Fleutot, Solenne'
_publ_section_title
;
 Crystal structure and DFT study of the zwitterionic form of
 3-{(E)-1-[(4-ethoxyphenyl)iminiumyl]ethyl}-6-methyl-2-oxo-2H-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
(E)-6-methyl-2-oxo-3-[1-(p-ethoxyiminio)ethyl]-2H-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 et al.,  2008)
;
_computing_publication_material
;
SHELXL2016/6 (Sheldrick, 2015), PLATON (Spek, 2009) and
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2016/6 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS2016/6 (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 ω 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/[σ²(Fo²)+(0.0419P)²+2.3424P] where P=(Fo²+2Fc²)/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 > 2σ(I)'
_cod_data_source_file            ex2003sup1.cif
_cod_data_source_block           I
_cod_database_code               2242325
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -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
O O1 0.37595(5) -0.09851(12) 0.25430(5) 0.0178(2) Uani d 1
O O2 0.46409(5) 0.36094(13) 0.13692(6) 0.0223(2) Uani d 1
O O3 0.48126(5) 0.09177(13) 0.11188(5) 0.0203(2) Uani d 1
O O4 0.28470(5) 0.53164(13) 0.53959(6) 0.0195(2) Uani d 1
N N1 0.35473(6) 0.20560(15) 0.29392(7) 0.0167(3) Uani d 1
H H1N 0.3533(9) 0.090(2) 0.2929(10) 0.033(5) Uiso d 1
C C1 0.51239(8) -0.1830(2) 0.07643(9) 0.0261(4) Uani d 1
H H1A 0.558974 -0.151115 0.094154 0.039 Uiso calc 1
H H1B 0.495675 -0.158824 0.020257 0.039 Uiso calc 1
H H1C 0.507565 -0.305845 0.085797 0.039 Uiso calc 1
C C2 0.47443(7) -0.08168(19) 0.12051(8) 0.0186(3) Uani d 1
C C3 0.43857(7) -0.14438(18) 0.16567(8) 0.0179(3) Uani d 1
H H3 0.433601 -0.265332 0.168807 0.021 Uiso calc 1
C C4 0.40712(6) -0.03355(17) 0.20989(8) 0.0154(3) Uani d 1
C C5 0.41363(6) 0.14995(17) 0.20071(7) 0.0153(3) Uani d 1
C C6 0.45203(6) 0.21302(18) 0.15026(8) 0.0169(3) Uani d 1
C C7 0.38639(6) 0.26807(18) 0.24515(8) 0.0162(3) Uani d 1
C C8 0.39081(7) 0.45891(18) 0.23821(8) 0.0203(3) Uani d 1
H H8C 0.374124 0.492541 0.183088 0.031 Uiso calc 1
H H8B 0.436806 0.495022 0.257827 0.031 Uiso calc 1
H H8A 0.364402 0.514294 0.269172 0.031 Uiso calc 1
C C9 0.33460(7) 0.29881(17) 0.35356(8) 0.0164(3) Uani d 1
C C10 0.26863(7) 0.30913(17) 0.35148(8) 0.0171(3) Uani d 1
H H10 0.236228 0.263353 0.308090 0.020 Uiso calc 1
C C11 0.24977(7) 0.38655(17) 0.41296(8) 0.0173(3) Uani d 1
H H11 0.204561 0.393367 0.411788 0.021 Uiso calc 1
C C12 0.29738(7) 0.45369(17) 0.47593(8) 0.0166(3) Uani d 1
C C13 0.36385(7) 0.44554(18) 0.47719(8) 0.0193(3) Uani d 1
H H13 0.396300 0.493437 0.519946 0.023 Uiso calc 1
C C14 0.38224(7) 0.36797(18) 0.41637(8) 0.0186(3) Uani d 1
H H14 0.427417 0.361699 0.417316 0.022 Uiso calc 1
C C15 0.21698(7) 0.56107(18) 0.53868(8) 0.0193(3) Uani d 1
H H15A 0.192613 0.451001 0.533117 0.023 Uiso calc 1
H H15B 0.195276 0.637069 0.494438 0.023 Uiso calc 1
C C16 0.21851(7) 0.64530(19) 0.61584(9) 0.0224(3) Uani d 1
H H16A 0.245376 0.749760 0.622067 0.034 Uiso calc 1
H H16B 0.237520 0.565599 0.658818 0.034 Uiso calc 1
H H16C 0.173613 0.675273 0.616796 0.034 Uiso calc 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
C2 O3 C6 122.46(11)
C12 O4 C15 118.24(11)
C7 N1 C9 126.68(12)
C7 N1 H1N 112.0(11)
C9 N1 H1N 120.3(11)
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 121.42(13)
C3 C2 C1 126.45(14)
O3 C2 C1 112.10(12)
C2 C3 C4 121.71(13)
C2 C3 H3 119.1
C4 C3 H3 119.1
O1 C4 C3 119.56(12)
O1 C4 C5 123.19(13)
C3 C4 C5 117.25(12)
C7 C5 C6 119.89(12)
C7 C5 C4 120.58(12)
C6 C5 C4 119.38(13)
O2 C6 O3 113.66(12)
O2 C6 C5 128.60(14)
O3 C6 C5 117.73(12)
N1 C7 C5 118.27(13)
N1 C7 C8 118.28(13)
C5 C7 C8 123.44(12)
C7 C8 H8C 109.5
C7 C8 H8B 109.5
H8C C8 H8B 109.5
C7 C8 H8A 109.5
H8C C8 H8A 109.5
H8B C8 H8A 109.5
C10 C9 C14 120.28(13)
C10 C9 N1 120.22(12)
C14 C9 N1 119.34(12)
C9 C10 C11 120.03(13)
C9 C10 H10 120.0
C11 C10 H10 120.0
C12 C11 C10 119.60(13)
C12 C11 H11 120.2
C10 C11 H11 120.2
O4 C12 C11 124.71(13)
O4 C12 C13 115.09(12)
C11 C12 C13 120.19(13)
C14 C13 C12 119.94(13)
C14 C13 H13 120.0
C12 C13 H13 120.0
C13 C14 C9 119.95(13)
C13 C14 H14 120.0
C9 C14 H14 120.0
O4 C15 C16 106.17(11)
O4 C15 H15A 110.5
C16 C15 H15A 110.5
O4 C15 H15B 110.5
C16 C15 H15B 110.5
H15A C15 H15B 108.7
C15 C16 H16A 109.5
C15 C16 H16B 109.5
H16A C16 H16B 109.5
C15 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C4 1.2585(16)
O2 C6 1.2154(17)
O3 C2 1.3698(17)
O3 C6 1.3988(18)
O4 C12 1.3680(16)
O4 C15 1.4427(16)
N1 C7 1.3182(18)
N1 C9 1.4358(18)
N1 H1N 0.902(19)
C1 C2 1.486(2)
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C2 C3 1.332(2)
C3 C4 1.440(2)
C3 H3 0.9500
C4 C5 1.4474(19)
C5 C7 1.427(2)
C5 C6 1.4431(19)
C7 C8 1.4946(19)
C8 H8C 0.9800
C8 H8B 0.9800
C8 H8A 0.9800
C9 C10 1.385(2)
C9 C14 1.392(2)
C10 C11 1.392(2)
C10 H10 0.9500
C11 C12 1.387(2)
C11 H11 0.9500
C12 C13 1.398(2)
C13 C14 1.378(2)
C13 H13 0.9500
C14 H14 0.9500
C15 C16 1.508(2)
C15 H15A 0.9900
C15 H15B 0.9900
C16 H16A 0.9800
C16 H16B 0.9800
C16 H16C 0.9800
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 H1N O1 . 0.90(2) 1.74(2) 2.5411(15) 147(2)
C1 H1B O3 5_655 0.98 2.57 3.4461(18) 149
C8 H8B O2 2_655 0.98 2.62 3.3478(17) 132
C10 H10 O1 4 0.95 2.56 3.2035(16) 125
C13 H13 O2 6_566 0.95 2.46 3.3950(17) 170
C15 H15A Cg1 7_556 0.99 2.74 3.618(2) 149
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
C6 O3 C2 C3 0.80(19)
C6 O3 C2 C1 -177.59(11)
O3 C2 C3 C4 -2.3(2)
C1 C2 C3 C4 175.89(13)
C2 C3 C4 O1 -177.10(12)
C2 C3 C4 C5 2.62(19)
O1 C4 C5 C7 2.5(2)
C3 C4 C5 C7 -177.19(12)
O1 C4 C5 C6 178.11(12)
C3 C4 C5 C6 -1.60(18)
C2 O3 C6 O2 178.87(11)
C2 O3 C6 C5 0.19(18)
C7 C5 C6 O2 -2.5(2)
C4 C5 C6 O2 -178.17(13)
C7 C5 C6 O3 175.91(11)
C4 C5 C6 O3 0.28(18)
C9 N1 C7 C5 167.68(12)
C9 N1 C7 C8 -13.4(2)
C6 C5 C7 N1 -176.26(12)
C4 C5 C7 N1 -0.68(18)
C6 C5 C7 C8 4.91(19)
C4 C5 C7 C8 -179.52(12)
C7 N1 C9 C10 119.67(15)
C7 N1 C9 C14 -64.93(18)
C14 C9 C10 C11 -1.0(2)
N1 C9 C10 C11 174.36(12)
C9 C10 C11 C12 0.3(2)
C15 O4 C12 C11 -5.99(19)
C15 O4 C12 C13 173.59(12)
C10 C11 C12 O4 -179.66(12)
C10 C11 C12 C13 0.8(2)
O4 C12 C13 C14 179.28(12)
C11 C12 C13 C14 -1.1(2)
C12 C13 C14 C9 0.4(2)
C10 C9 C14 C13 0.7(2)
N1 C9 C14 C13 -174.74(12)
C12 O4 C15 C16 179.27(11)

_cod_database_fobs_code 2242325
