#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/09/2240920.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_2240920
loop_
_publ_author_name
'Djedouani, Amel'
'Boufas, Sihem'
'Cleymand, Franck'
'François, Michel'
'Fleutot, Solenne'
_publ_section_title
;
 Crystal structure of
 (E)-4-hydroxy-3-{1-[(4-hydroxyphenyl)imino]ethyl}-6-methyl-2H-pyran-2-one
;
_journal_coeditor_code           HB7460
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o564
_journal_page_last               o565
_journal_paper_doi               10.1107/S2056989015012840
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C14 H13 N O4'
_chemical_formula_moiety         'C14 H13 N O4'
_chemical_formula_sum            'C14 H13 N O4'
_chemical_formula_weight         259.26
_chemical_name_systematic
(E)-4-hydroxy-3-{1-[(4-hydroxyphenyl)imino]ethyl}-6-methyl-2H-pyran-2-one
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90
_cell_angle_beta                 99.896(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8730(5)
_cell_length_b                   11.7930(8)
_cell_length_c                   13.5330(8)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.91
_cell_volume                     1237.79(14)
_computing_cell_refinement
;
DENZO-SMN  (Otwinowski & Minor, 1997)
;
_computing_data_collection
;
COLLECT (Nonius, 2002)
;
_computing_data_reduction
;
EvalCCD (Duisenberg et al.,  2003)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al.,
2006)
;
_computing_publication_material
;
WinGX (Farrugia, 2012) and PARST (Nardelli, 1995)
;
_computing_structure_refinement
;
olex2.refine (Dolomanov et al.,  2009)
;
_computing_structure_solution
;
SIR97 (Altomare et al.,  1999)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.9931
_diffrn_measured_fraction_theta_max 0.9931
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enraf--Nonius FR590'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.026
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17976
_diffrn_reflns_theta_full        26.665
_diffrn_reflns_theta_max         26.67
_diffrn_reflns_theta_min         2.31
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9472
_exptl_absorpt_correction_T_min  0.8752
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2002)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.3911
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             544.3271
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.5375
_refine_diff_density_min         -0.3745
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2582
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0472
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0655P)²+0.6848P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1361
_refine_ls_wR_factor_ref         0.1476
_reflns_number_gt                2061
_reflns_number_total             2582
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb7460sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2240920
_cod_database_fobs_code          2240920
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
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_occupancy
O O1 0.6637(2) -0.08723(12) 0.50633(10) 0.0520(4) Uani 1
H H1 0.6696(2) -0.05535(12) 0.45317(10) 0.0779(6) Uiso 1
O O2 0.4993(2) 0.21003(13) -0.00201(10) 0.0543(4) Uani 1
H H2 0.4624(2) 0.27519(13) -0.00450(10) 0.0815(7) Uiso 1
O O3 1.0343(3) 0.20593(17) 0.65333(13) 0.0814(7) Uani 1
O O4 0.92760(19) 0.08216(12) 0.74439(9) 0.0443(4) Uani 1
C C1 0.6821(3) 0.11371(17) 0.29043(13) 0.0390(4) Uani 1
C C2 0.7568(3) -0.07161(18) 0.67874(15) 0.0444(5) Uani 1
H H2a 0.7031(3) -0.13959(18) 0.68968(15) 0.0533(6) Uiso 1
C C3 0.6279(3) 0.07382(18) 0.11415(14) 0.0433(5) Uani 1
H H3 0.6333(3) 0.02421(18) 0.06136(14) 0.0520(6) Uiso 1
C C4 0.7488(3) -0.03156(16) 0.57810(14) 0.0391(4) Uani 1
C C5 0.8305(3) 0.12191(16) 0.46720(14) 0.0382(4) Uani 1
C C6 0.6138(3) 0.22135(17) 0.27136(14) 0.0416(5) Uani 1
H H6 0.6089(3) 0.27092(17) 0.32425(14) 0.0499(6) Uiso 1
C C7 0.5531(3) 0.25514(17) 0.17428(14) 0.0416(5) Uani 1
H H7 0.5074(3) 0.32751(17) 0.16191(14) 0.0499(6) Uiso 1
C C8 0.8390(3) -0.01396(17) 0.75665(14) 0.0407(5) Uani 1
C C9 0.9259(3) 0.22691(19) 0.44950(16) 0.0489(5) Uani 1
H H9a 0.9215(18) 0.2372(8) 0.37874(17) 0.0733(8) Uiso 1
H H9b 0.8738(13) 0.2909(3) 0.4764(11) 0.0733(8) Uiso 1
H H9c 1.0438(6) 0.2203(6) 0.4820(10) 0.0733(8) Uiso 1
C C10 0.5598(3) 0.18172(17) 0.09476(13) 0.0389(4) Uani 1
C C11 0.9398(3) 0.12553(18) 0.65006(15) 0.0454(5) Uani 1
C C12 0.8492(3) -0.0416(2) 0.86465(15) 0.0554(6) Uani 1
H H12a 0.9678(4) -0.0434(15) 0.8967(3) 0.0831(9) Uiso 1
H H12b 0.789(2) 0.0151(9) 0.8959(3) 0.0831(9) Uiso 1
H H12c 0.797(2) -0.1144(7) 0.87109(15) 0.0831(9) Uiso 1
C C13 0.6877(3) 0.03998(17) 0.21150(15) 0.0419(5) Uani 1
H H13 0.7319(3) -0.03271(17) 0.22414(15) 0.0502(6) Uiso 1
C C14 0.8397(2) 0.07122(16) 0.56378(13) 0.0368(4) Uani 1
N N1 0.7321(2) 0.07168(14) 0.39048(12) 0.0434(4) Uani 1
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
H 0 0 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
C 0.00347 0.00161 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
O 0.01158 0.00611 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
N 0.00653 0.00323 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C4 O1 H1 109.5
C10 O2 H2 109.5
C11 O4 C8 122.46(15)
C13 C1 C6 119.66(17)
N1 C1 C6 121.88(17)
N1 C1 C13 118.18(18)
C4 C2 H2a 119.25(12)
C8 C2 H2a 119.25(12)
C8 C2 C4 121.5(2)
C10 C3 H3 119.90(11)
C13 C3 H3 119.90(12)
C13 C3 C10 120.19(18)
C2 C4 O1 119.33(18)
C14 C4 O1 122.99(17)
C14 C4 C2 117.68(17)
C14 C5 C9 123.23(17)
N1 C5 C9 119.29(17)
N1 C5 C14 117.48(18)
H6 C6 C1 119.91(11)
C7 C6 C1 120.17(18)
C7 C6 H6 119.91(12)
H7 C7 C6 119.82(12)
C10 C7 C6 120.36(18)
C10 C7 H7 119.82(11)
C2 C8 O4 121.50(18)
C12 C8 O4 111.21(18)
C12 C8 C2 127.3(2)
H9a C9 C5 109.5
H9b C9 C5 109.5
H9b C9 H9a 109.5
H9c C9 C5 109.5
H9c C9 H9a 109.5
H9c C9 H9b 109.5
C3 C10 O2 117.93(17)
C7 C10 O2 122.75(18)
C7 C10 C3 119.31(17)
O4 C11 O3 113.30(18)
C14 C11 O3 129.00(19)
C14 C11 O4 117.69(18)
H12a C12 C8 109.5
H12b C12 C8 109.5
H12b C12 H12a 109.5
H12c C12 C8 109.5
H12c C12 H12a 109.5
H12c C12 H12b 109.5
C3 C13 C1 120.30(18)
H13 C13 C1 119.85(11)
H13 C13 C3 119.85(12)
C5 C14 C4 121.89(17)
C11 C14 C4 118.74(17)
C11 C14 C5 119.35(18)
C5 N1 C1 127.99(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 H1 0.82
O1 C4 1.265(2)
O2 H2 0.82
O2 C10 1.356(2)
O3 C11 1.201(3)
O4 C8 1.356(2)
O4 C11 1.394(2)
C1 C6 1.385(3)
C1 C13 1.384(3)
C1 N1 1.432(2)
C2 H2a 0.93
C2 C4 1.433(3)
C2 C8 1.326(3)
C3 H3 0.93
C3 C10 1.388(3)
C3 C13 1.380(3)
C4 C14 1.438(3)
C5 C9 1.489(3)
C5 C14 1.428(3)
C5 N1 1.324(2)
C6 H6 0.93
C6 C7 1.377(3)
C7 H7 0.93
C7 C10 1.389(3)
C8 C12 1.486(3)
C9 H9a 0.96
C9 H9b 0.96
C9 H9c 0.96
C11 C14 1.442(3)
C12 H12a 0.96
C12 H12b 0.96
C12 H12c 0.96
C13 H13 0.93
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
_geom_hbond_publ_flag
O1 H1 N1 1_555 0.82 1.83 2.560(2) 147 yes
O2 H2 O1 2_655 0.82 1.90 2.710(2) 169 yes
C12 H12B O3 2_746 0.96 2.55 3.137(3) 120 yes
