##############################################################################
#                                                                            #
# 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 Acta Crystallographica 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
3-[1-(2-Hydroxyanilino)ethylidene]-3<i>H</i>-chromen-2,4-dione
;
_chemical_name_common     phenylamino-3H-chromenedione
_chemical_formula_moiety     'C17 H13 N O4'
_chemical_formula_sum     'C17 H13 N O4'
_chemical_formula_iupac     'C17 H13 N O4'
_chemical_formula_weight     295.29
_chemical_melting_point     446
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     -P2yn
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     12.5596(4)
_cell_length_b     7.5870(3)
_cell_length_c     14.3433(6)
_cell_angle_alpha     90.00
_cell_angle_beta     94.660(2)
_cell_angle_gamma     90.00
_cell_volume     1362.25(9)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1721
_cell_measurement_theta_min     ?
_cell_measurement_theta_max     ?
_cell_measurement_temperature     293(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.16
_exptl_crystal_size_mid     0.13
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.440
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     616
_exptl_absorpt_coefficient_mu     0.104
_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     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART CCD area-detector'
_diffrn_measurement_method     '\f and \w scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     11784
_diffrn_reflns_av_R_equivalents     0.0526
_diffrn_reflns_av_sigmaI/netI     0.0730
_diffrn_reflns_theta_min     2.07
_diffrn_reflns_theta_max     29.77
_diffrn_reflns_theta_full     29.77
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -14
_diffrn_reflns_limit_h_max     17
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -19
_diffrn_reflns_limit_l_max     20
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of <i>F</i>^2^ against ALL reflections. The weighted <i>R</i>-factor
<i>wR</i> and goodness of fit <i>S</i> are based on <i>F</i>^2^, conventional
<i>R</i>-factors <i>R</i> are based on <i>F</i>, with <i>F</i> set to zero for
negative <i>F</i>^2^. The threshold expression of <i>F</i>^2^ >
\s(<i>F</i>^2^) is used only for calculating <i>R</i>-factors(gt) <i>etc</i>.
and is not relevant to the choice of reflections for refinement.
<i>R</i>-factors based on <i>F</i>^2^ are statistically about twice as large
as those based on <i>F</i>, and <i>R</i>- factors based on ALL data will be
even larger.
;
_reflns_number_total     3891
_reflns_number_gt     1721
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1466
_refine_ls_R_factor_gt     0.0579
_refine_ls_wR_factor_gt     0.1434
_refine_ls_wR_factor_ref     0.1941
_refine_ls_goodness_of_fit_ref     0.908
_refine_ls_restrained_S_all     0.908
_refine_ls_number_reflns     3891
_refine_ls_number_parameters     251
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[\s^2^(Fo^2^)+(0.0922P)^2^+0.2201P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.225
_refine_diff_density_min     -0.199
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0030 0.0020
                         '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' 0.0060 0.0030
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0110 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 2001)'
_computing_cell_refinement     'SMART (Bruker, 2001)'
_computing_data_reduction     'SAINT (Bruker, 2001)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material     'WinGX (Farrugia, 2012)'
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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.12600(13) 0.1466(2) 0.90032(12) 0.0480(5) Uani d . 1 1 . .
    N N1 0.22554(16) 0.0473(3) 1.22516(14) 0.0375(5) Uani d . 1 1 . .
    C C1 0.17836(17) 0.0955(3) 1.06478(16) 0.0350(5) Uani d . 1 1 . .
    O O3 0.34691(12) -0.0400(2) 1.09988(12) 0.0484(5) Uani d . 1 1 . .
    C C2 0.27686(18) 0.0180(3) 1.04068(17) 0.0378(6) Uani d . 1 1 . .
    C C3 0.29714(18) 0.0128(3) 0.94130(17) 0.0389(6) Uani d . 1 1 . .
    C C4 0.21353(18) 0.0298(3) 1.32227(17) 0.0368(6) Uani d . 1 1 . .
    O O4 0.38154(13) 0.1659(2) 1.35092(12) 0.0473(5) Uani d . 1 1 . .
    H H12 0.4244 0.1965 1.3941 0.071 Uiso calc R 1 1 . .
    C C5 0.15554(17) 0.1107(3) 1.16048(17) 0.0363(6) Uani d . 1 1 . .
    O O2 0.01364(14) 0.2201(3) 1.00033(13) 0.0556(5) Uani d . 1 1 . .
    C C6 0.29532(19) 0.0900(3) 1.38614(18) 0.0376(6) Uani d . 1 1 . .
    C C7 0.22130(19) 0.0795(3) 0.87552(18) 0.0417(6) Uani d . 1 1 . .
    C C8 0.2850(2) 0.0704(3) 1.48055(18) 0.0439(6) Uani d . 1 1 . .
    H H4 0.3384 0.1118 1.5238 0.053 Uiso calc R 1 1 . .
    C C9 0.05868(19) 0.2032(4) 1.19047(19) 0.0475(7) Uani d . 1 1 . .
    H H5 0.0586 0.1977 1.2573 0.071 Uiso calc R 1 1 . .
    H H11 -0.0045 0.1470 1.1623 0.071 Uiso calc R 1 1 . .
    H H7 0.0598 0.3242 1.1710 0.071 Uiso calc R 1 1 . .
    C C10 0.2392(2) 0.0838(4) 0.78132(19) 0.0546(7) Uani d . 1 1 . .
    H H10 0.1871 0.1274 0.7375 0.065 Uiso calc R 1 1 . .
    C C11 0.10187(19) 0.1569(3) 0.99164(18) 0.0416(6) Uani d . 1 1 . .
    C C12 0.3922(2) -0.0510(3) 0.9114(2) 0.0481(7) Uani d . 1 1 . .
    H H1 0.4431 -0.0990 0.9548 0.058 Uiso calc R 1 1 . .
    C C13 0.12623(19) -0.0559(3) 1.35386(19) 0.0451(7) Uani d . 1 1 . .
    H H2 0.0735 -0.1007 1.3111 0.054 Uiso calc R 1 1 . .
    C C14 0.1168(2) -0.0752(4) 1.4483(2) 0.0503(7) Uani d . 1 1 . .
    H H3 0.0575 -0.1314 1.4695 0.060 Uiso calc R 1 1 . .
    C C15 0.4121(2) -0.0446(4) 0.8187(2) 0.0545(7) Uani d . 1 1 . .
    H H8 0.4768 -0.0848 0.7996 0.065 Uiso calc R 1 1 . .
    C C16 0.1960(2) -0.0104(4) 1.51091(19) 0.0497(7) Uani d . 1 1 . .
    H H6 0.1893 -0.0214 1.5747 0.060 Uiso calc R 1 1 . .
    C C17 0.3343(2) 0.0230(4) 0.7537(2) 0.0583(8) Uani d . 1 1 . .
    H H9 0.3471 0.0268 0.6908 0.070 Uiso calc R 1 1 . .
    H H13 0.283(2) 0.007(4) 1.201(2) 0.061(9) Uiso d . 1 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
    O1 0.0451(10) 0.0600(12) 0.0366(10) 0.0120(9) -0.0099(8) 0.0012(9)
    N1 0.0327(11) 0.0452(12) 0.0330(11) 0.0007(9) -0.0072(9) -0.0010(9)
    C1 0.0327(11) 0.0370(13) 0.0335(13) 0.0004(10) -0.0089(10) 0.0011(10)
    O3 0.0378(9) 0.0621(12) 0.0433(10) 0.0091(8) -0.0085(8) 0.0041(9)
    C2 0.0347(12) 0.0368(13) 0.0398(13) -0.0011(10) -0.0104(10) 0.0017(11)
    C3 0.0387(13) 0.0355(13) 0.0413(14) -0.0040(11) -0.0045(11) -0.0031(11)
    C4 0.0355(12) 0.0391(13) 0.0342(13) 0.0009(10) -0.0057(10) -0.0007(11)
    O4 0.0390(9) 0.0621(12) 0.0390(10) -0.0135(8) -0.0080(8) 0.0009(9)
    C5 0.0339(12) 0.0330(13) 0.0403(14) -0.0055(10) -0.0082(10) -0.0012(10)
    O2 0.0406(10) 0.0748(14) 0.0484(11) 0.0151(9) -0.0141(8) 0.0016(10)
    C6 0.0403(13) 0.0340(13) 0.0375(13) -0.0002(10) -0.0032(10) -0.0001(11)
    C7 0.0436(14) 0.0406(14) 0.0393(14) -0.0002(11) -0.0069(11) -0.0026(11)
    C8 0.0474(14) 0.0477(16) 0.0351(14) -0.0028(12) -0.0063(11) -0.0026(12)
    C9 0.0409(13) 0.0541(17) 0.0462(16) 0.0054(12) -0.0047(12) -0.0015(13)
    C10 0.0630(18) 0.0593(18) 0.0395(16) 0.0063(15) -0.0078(13) 0.0033(13)
    C11 0.0399(13) 0.0428(15) 0.0400(15) -0.0012(12) -0.0094(11) 0.0003(12)
    C12 0.0413(13) 0.0493(16) 0.0519(17) 0.0012(12) -0.0073(12) -0.0047(13)
    C13 0.0377(13) 0.0486(16) 0.0475(16) -0.0029(11) -0.0056(12) -0.0019(12)
    C14 0.0471(15) 0.0493(16) 0.0554(18) -0.0022(12) 0.0104(13) 0.0016(14)
    C15 0.0489(15) 0.0655(19) 0.0492(17) -0.0035(14) 0.0040(13) -0.0079(15)
    C16 0.0601(17) 0.0510(16) 0.0384(14) 0.0040(14) 0.0057(13) 0.0006(13)
    C17 0.0656(18) 0.067(2) 0.0427(16) -0.0056(16) 0.0035(14) -0.0031(15)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
    O1 C7 . 1.374(3) ?
    O1 C11 . 1.370(3) ?
    N1 C5 . 1.316(3) ?
    N1 C4 . 1.419(3) ?
    N1 H13 . 0.88(3) ?
    C1 C5 . 1.429(3) ?
    C1 C2 . 1.437(3) ?
    C1 C11 . 1.441(3) ?
    O3 C2 . 1.252(3) ?
    C2 C3 . 1.469(3) ?
    C3 C7 . 1.381(3) ?
    C3 C12 . 1.388(3) ?
    C4 C13 . 1.382(3) ?
    C4 C6 . 1.396(3) ?
    O4 C6 . 1.359(3) ?
    O4 H12 . 0.8200 ?
    C5 C9 . 1.498(3) ?
    O2 C11 . 1.223(3) ?
    C6 C8 . 1.379(3) ?
    C7 C10 . 1.388(4) ?
    C8 C16 . 1.376(4) ?
    C8 H4 . 0.9300 ?
    C9 H5 . 0.9600 ?
    C9 H11 . 0.9600 ?
    C9 H7 . 0.9600 ?
    C10 C17 . 1.369(4) ?
    C10 H10 . 0.9300 ?
    C12 C15 . 1.373(4) ?
    C12 H1 . 0.9300 ?
    C13 C14 . 1.376(4) ?
    C13 H2 . 0.9300 ?
    C14 C16 . 1.376(4) ?
    C14 H3 . 0.9300 ?
    C15 C17 . 1.393(4) ?
    C15 H8 . 0.9300 ?
    C16 H6 . 0.9300 ?
    C17 H9 . 0.9300 ?
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
    C7 O1 C11 . . 122.26(19) ?
    C5 N1 C4 . . 127.4(2) ?
    C5 N1 H13 . . 112(2) ?
    C4 N1 H13 . . 121(2) ?
    C5 C1 C2 . . 120.5(2) ?
    C5 C1 C11 . . 119.9(2) ?
    C2 C1 C11 . . 119.6(2) ?
    O3 C2 C1 . . 123.5(2) ?
    O3 C2 C3 . . 118.8(2) ?
    C1 C2 C3 . . 117.7(2) ?
    C7 C3 C12 . . 118.6(2) ?
    C7 C3 C2 . . 119.3(2) ?
    C12 C3 C2 . . 122.0(2) ?
    C13 C4 C6 . . 120.0(2) ?
    C13 C4 N1 . . 121.1(2) ?
    C6 C4 N1 . . 118.8(2) ?
    C6 O4 H12 . . 109.5 ?
    N1 C5 C1 . . 118.2(2) ?
    N1 C5 C9 . . 118.7(2) ?
    C1 C5 C9 . . 123.0(2) ?
    O4 C6 C8 . . 123.5(2) ?
    O4 C6 C4 . . 117.4(2) ?
    C8 C6 C4 . . 119.1(2) ?
    O1 C7 C3 . . 121.7(2) ?
    O1 C7 C10 . . 117.2(2) ?
    C3 C7 C10 . . 121.1(2) ?
    C6 C8 C16 . . 120.1(2) ?
    C6 C8 H4 . . 119.9 ?
    C16 C8 H4 . . 119.9 ?
    C5 C9 H5 . . 109.5 ?
    C5 C9 H11 . . 109.5 ?
    H5 C9 H11 . . 109.5 ?
    C5 C9 H7 . . 109.5 ?
    H5 C9 H7 . . 109.5 ?
    H11 C9 H7 . . 109.5 ?
    C17 C10 C7 . . 119.2(3) ?
    C17 C10 H10 . . 120.4 ?
    C7 C10 H10 . . 120.4 ?
    O2 C11 O1 . . 113.1(2) ?
    O2 C11 C1 . . 127.5(2) ?
    O1 C11 C1 . . 119.4(2) ?
    C15 C12 C3 . . 121.0(3) ?
    C15 C12 H1 . . 119.5 ?
    C3 C12 H1 . . 119.5 ?
    C4 C13 C14 . . 120.4(2) ?
    C4 C13 H2 . . 119.8 ?
    C14 C13 H2 . . 119.8 ?
    C13 C14 C16 . . 119.3(2) ?
    C13 C14 H3 . . 120.4 ?
    C16 C14 H3 . . 120.4 ?
    C12 C15 C17 . . 119.3(3) ?
    C12 C15 H8 . . 120.4 ?
    C17 C15 H8 . . 120.4 ?
    C8 C16 C14 . . 121.0(3) ?
    C8 C16 H6 . . 119.5 ?
    C14 C16 H6 . . 119.5 ?
    C10 C17 C15 . . 120.7(3) ?
    C10 C17 H9 . . 119.6 ?
    C15 C17 H9 . . 119.6 ?
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
    O4 H12 O2 4_666 0.82 1.92 2.742(2) 174.5
    N1 H13 O3 . 0.88(3) 1.75(3) 2.537(3) 148(3)
    C8 H4 O2 4_666 0.93 2.59 3.274(3) 130.8
data_global
_journal_date_recd_electronic     2013-06-25
_journal_date_accepted     2013-07-12
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2013
_journal_volume     69
_journal_issue      8
_journal_page_first     o1296
_journal_page_last     o1296
_journal_paper_category     QO
_journal_paper_doi     10.1107/S160053681301934X
_journal_coeditor_code     FF2111
_publ_contact_author_name     'Ben Hassen, Rached'
_publ_contact_author_address
;
Unit\'e de chimie des Mat\'eriaux et de l'environnement,
ISSBAT, Universit\'e de Tunis-ElManar,
9 Avenue Dr. Zoheir SAFI, 1006 Tunis, Tunisia
;
_publ_contact_author_email     'rached.benhassen@fss.rnu.tn'
_publ_contact_author_fax     '216 71 57 35 26'
_publ_contact_author_phone     '216 98 69 27 45'
_publ_section_title
;
3-[1-(2-Hydroxyanilino)ethylidene]-3<i>H</i>-chromen-2,4-dione
;
loop_
    _publ_author_name
    _publ_author_address
    'Brahmia, Ameni'
;
Unit\'e de Chimie des Mat\'eriaux et de l'Environnement,
ISSBAT, Universit\'e de Tunis-ElManar,
9 Avenue Dr Zoheir SAFI, 1006 Tunis, Tunisia
;
    'Ben Ayed, Taicir'
;
INSAT, Universit\'e de Carthage, Centre Urbain Nord,
BP 676, 1080 Tunis Cedex, Tunis, Tunisia
;
    'Ben Hassen, Rached'
;
Unit\'e de Chimie des Mat\'eriaux et de l'Environnement,
ISSBAT, Universit\'e de Tunis-ElManar,
9 Avenue Dr Zoheir SAFI, 1006 Tunis, Tunisia
;