##############################################################################
#                                                                            #
# 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
;
4-Hydroxy-3-[(<i>E</i>)-3-phenylprop-2-enoyl]-2<i>H</i>-chromen-2-one
;
_chemical_name_common     phenyl-4-hydroxycoumarinchalcone
_chemical_formula_moiety     'C18 H12 O4'
_chemical_formula_sum     'C18 H12 O4'
_chemical_formula_iupac     'C18 H12 O4'
_chemical_formula_weight     292.28
_chemical_melting_point     489
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     -P2ybc
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     11.8040(5)
_cell_length_b     3.8860(5)
_cell_length_c     29.7190(5)
_cell_angle_alpha     90.00
_cell_angle_beta     97.164(5)
_cell_angle_gamma     90.00
_cell_volume     1352.58(18)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     203
_cell_measurement_theta_min     ?
_cell_measurement_theta_max     ?
_cell_measurement_temperature     296(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.3
_exptl_crystal_size_mid     0.14
_exptl_crystal_size_min     0.06
_exptl_crystal_density_diffrn     1.435
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     608
_exptl_absorpt_coefficient_mu     0.102
_exptl_absorpt_correction_type     numerical
_exptl_absorpt_process_details     '(SADABS; Bruker, 2003)'
_exptl_absorpt_correction_T_min     0.8614
_exptl_absorpt_correction_T_max     0.8645
_exptl_special_details
;
;
_diffrn_ambient_temperature     296(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'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     11154
_diffrn_reflns_av_R_equivalents     0.0700
_diffrn_reflns_av_sigmaI/netI     0.0731
_diffrn_reflns_theta_min     1.38
_diffrn_reflns_theta_max     27.23
_diffrn_reflns_theta_full     27.23
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -15
_diffrn_reflns_limit_h_max     14
_diffrn_reflns_limit_k_min     -4
_diffrn_reflns_limit_k_max     4
_diffrn_reflns_limit_l_min     -38
_diffrn_reflns_limit_l_max     37
_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     2983
_reflns_number_gt     1404
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1738
_refine_ls_R_factor_gt     0.0692
_refine_ls_wR_factor_gt     0.1768
_refine_ls_wR_factor_ref     0.2996
_refine_ls_goodness_of_fit_ref     1.041
_refine_ls_restrained_S_all     1.041
_refine_ls_number_reflns     2983
_refine_ls_number_parameters     203
_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^)+(0.1616P)^2^] 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     0.539
_refine_diff_density_min     -0.686
_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' 0.0033 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'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 2003)'
_computing_cell_refinement     'SAINT (Bruker, 2003)'
_computing_data_reduction     'SAINT (Bruker, 2003)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'DIAMOND (Brandenburg, 1999)'
_computing_publication_material     'WinGX (Farrugia, 1999)'
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 0.0403(2) 0.2994(9) 0.14926(11) 0.0562(9) Uani d . 1 1 . .
    O O2 0.0632(2) 0.0415(9) 0.07711(9) 0.0559(9) Uani d . 1 1 . .
    C C1 0.1298(4) 0.5245(10) 0.23674(14) 0.0449(11) Uani d . 1 1 . .
    H H1 0.0526 0.5667 0.2281 0.054 Uiso calc R 1 1 . .
    C C2 0.1481(3) 0.2566(10) 0.16162(13) 0.0372(9) Uani d . 1 1 . .
    C C10 0.1719(3) 0.0080(10) 0.08756(13) 0.0403(10) Uani d . 1 1 . .
    C C3 0.1795(4) 0.6154(11) 0.27952(14) 0.0531(12) Uani d . 1 1 . .
    H H3 0.1357 0.7162 0.2999 0.064 Uiso calc R 1 1 . .
    C C14 0.1811(4) -0.5082(11) -0.06124(13) 0.0473(11) Uani d . 1 1 . .
    H H12 0.1031 -0.5413 -0.0610 0.057 Uiso calc R 1 1 . .
    C C12 0.1891(4) -0.2364(10) 0.01330(13) 0.0418(10) Uani d . 1 1 . .
    H H6 0.1098 -0.2428 0.0093 0.050 Uiso calc R 1 1 . .
    C C7 0.1950(3) 0.3694(9) 0.20651(12) 0.0362(9) Uani d . 1 1 . .
    C C8 0.2206(3) 0.1046(10) 0.13289(12) 0.0363(9) Uani d . 1 1 . .
    C C15 0.2328(4) -0.6146(11) -0.09835(14) 0.0546(13) Uani d . 1 1 . .
    H H11 0.1895 -0.7214 -0.1227 0.065 Uiso calc R 1 1 . .
    C C11 0.2385(4) -0.1217(10) 0.05304(13) 0.0421(10) Uani d . 1 1 . .
    H H7 0.3177 -0.1241 0.0590 0.050 Uiso calc R 1 1 . .
    C C4 0.2948(4) 0.5566(11) 0.29212(14) 0.0532(12) Uani d . 1 1 . .
    H H4 0.3282 0.6208 0.3209 0.064 Uiso calc R 1 1 . .
    C C6 0.3095(3) 0.3138(10) 0.22020(12) 0.0379(9) Uani d . 1 1 . .
    C C9 0.3401(4) 0.0457(11) 0.14931(13) 0.0445(10) Uani d . 1 1 . .
    C C16 0.3483(4) -0.5624(11) -0.09925(14) 0.0536(12) Uani d . 1 1 . .
    H H10 0.3824 -0.6308 -0.1244 0.064 Uiso calc R 1 1 . .
    C C5 0.3595(4) 0.4068(11) 0.26304(14) 0.0507(11) Uani d . 1 1 . .
    H H5 0.4368 0.3669 0.2718 0.061 Uiso calc R 1 1 . .
    O O3 0.3791(2) 0.1608(8) 0.19242(9) 0.0485(8) Uani d . 1 1 . .
    C C17 0.4132(4) -0.4082(12) -0.06275(15) 0.0538(12) Uani d . 1 1 . .
    H H9 0.4912 -0.3759 -0.0630 0.065 Uiso calc R 1 1 . .
    O O4 0.4098(3) -0.0973(11) 0.12993(11) 0.0753(12) Uani d . 1 1 . .
    C C18 0.3610(4) -0.3021(11) -0.02576(13) 0.0471(11) Uani d . 1 1 . .
    H H8 0.4046 -0.1954 -0.0015 0.057 Uiso calc R 1 1 . .
    C C13 0.2453(4) -0.3519(10) -0.02429(13) 0.0386(9) Uani d . 1 1 . .
    H H2 0.022(6) 0.181(17) 0.120(2) 0.13(2) 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 0.0409(18) 0.085(2) 0.0422(18) 0.0068(16) 0.0031(14) -0.0133(17)
    O2 0.0428(18) 0.083(2) 0.0404(17) 0.0022(16) -0.0005(14) -0.0144(16)
    C1 0.056(3) 0.040(2) 0.041(2) 0.0013(19) 0.017(2) 0.0005(18)
    C2 0.040(2) 0.038(2) 0.034(2) -0.0007(17) 0.0080(17) 0.0014(17)
    C10 0.045(2) 0.040(2) 0.037(2) -0.0008(18) 0.0070(19) 0.0017(18)
    C3 0.086(4) 0.044(2) 0.034(2) -0.002(2) 0.021(2) -0.0042(18)
    C14 0.053(3) 0.049(2) 0.038(2) 0.005(2) 0.001(2) 0.0004(19)
    C12 0.048(2) 0.044(2) 0.034(2) 0.0010(19) 0.0072(19) -0.0007(18)
    C7 0.045(2) 0.036(2) 0.028(2) -0.0032(17) 0.0103(17) 0.0047(16)
    C8 0.042(2) 0.038(2) 0.029(2) -0.0014(17) 0.0038(17) 0.0021(16)
    C15 0.084(4) 0.047(3) 0.030(2) 0.011(2) 0.001(2) -0.0057(19)
    C11 0.046(2) 0.047(2) 0.033(2) 0.0025(19) 0.0059(18) -0.0005(18)
    C4 0.076(3) 0.050(3) 0.032(2) -0.010(2) 0.000(2) -0.0010(19)
    C6 0.043(2) 0.041(2) 0.030(2) -0.0036(18) 0.0080(17) 0.0012(17)
    C9 0.043(2) 0.056(3) 0.034(2) 0.008(2) 0.0060(19) -0.0003(19)
    C16 0.078(4) 0.052(3) 0.034(2) 0.018(2) 0.016(2) 0.003(2)
    C5 0.055(3) 0.055(3) 0.041(2) -0.009(2) -0.002(2) 0.000(2)
    O3 0.0369(16) 0.072(2) 0.0357(16) 0.0048(15) 0.0014(12) -0.0042(14)
    C17 0.060(3) 0.056(3) 0.047(3) 0.007(2) 0.014(2) 0.003(2)
    O4 0.053(2) 0.123(3) 0.050(2) 0.032(2) 0.0068(17) -0.021(2)
    C18 0.060(3) 0.047(2) 0.033(2) 0.001(2) 0.005(2) 0.0004(18)
    C13 0.052(2) 0.035(2) 0.029(2) 0.0043(18) 0.0049(18) 0.0029(16)
_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 C2 . 1.290(5) ?
    O1 H2 . 0.99(7) ?
    O2 C10 . 1.289(5) ?
    C1 C3 . 1.378(6) ?
    C1 C7 . 1.391(5) ?
    C1 H1 . 0.9300 ?
    C2 C8 . 1.411(5) ?
    C2 C7 . 1.447(5) ?
    C10 C8 . 1.447(5) ?
    C10 C11 . 1.457(5) ?
    C3 C4 . 1.385(7) ?
    C3 H3 . 0.9300 ?
    C14 C15 . 1.388(6) ?
    C14 C13 . 1.394(6) ?
    C14 H12 . 0.9300 ?
    C12 C11 . 1.327(5) ?
    C12 C13 . 1.440(5) ?
    C12 H6 . 0.9300 ?
    C7 C6 . 1.379(5) ?
    C8 C9 . 1.452(5) ?
    C15 C16 . 1.383(7) ?
    C15 H11 . 0.9300 ?
    C11 H7 . 0.9300 ?
    C4 C5 . 1.354(6) ?
    C4 H4 . 0.9300 ?
    C6 O3 . 1.371(4) ?
    C6 C5 . 1.383(5) ?
    C9 O4 . 1.198(5) ?
    C9 O3 . 1.381(5) ?
    C16 C17 . 1.384(6) ?
    C16 H10 . 0.9300 ?
    C5 H5 . 0.9300 ?
    C17 C18 . 1.388(6) ?
    C17 H9 . 0.9300 ?
    C18 C13 . 1.385(6) ?
    C18 H8 . 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
    C2 O1 H2 . . 107(4) ?
    C3 C1 C7 . . 120.0(4) ?
    C3 C1 H1 . . 120.0 ?
    C7 C1 H1 . . 120.0 ?
    O1 C2 C8 . . 122.2(4) ?
    O1 C2 C7 . . 118.3(3) ?
    C8 C2 C7 . . 119.5(4) ?
    O2 C10 C8 . . 117.8(4) ?
    O2 C10 C11 . . 118.2(4) ?
    C8 C10 C11 . . 124.0(4) ?
    C1 C3 C4 . . 119.9(4) ?
    C1 C3 H3 . . 120.1 ?
    C4 C3 H3 . . 120.1 ?
    C15 C14 C13 . . 120.4(4) ?
    C15 C14 H12 . . 119.8 ?
    C13 C14 H12 . . 119.8 ?
    C11 C12 C13 . . 127.0(4) ?
    C11 C12 H6 . . 116.5 ?
    C13 C12 H6 . . 116.5 ?
    C6 C7 C1 . . 118.6(4) ?
    C6 C7 C2 . . 118.2(3) ?
    C1 C7 C2 . . 123.2(4) ?
    C2 C8 C10 . . 118.1(4) ?
    C2 C8 C9 . . 120.0(3) ?
    C10 C8 C9 . . 121.9(3) ?
    C16 C15 C14 . . 120.3(4) ?
    C16 C15 H11 . . 119.9 ?
    C14 C15 H11 . . 119.9 ?
    C12 C11 C10 . . 121.8(4) ?
    C12 C11 H7 . . 119.1 ?
    C10 C11 H7 . . 119.1 ?
    C5 C4 C3 . . 120.8(4) ?
    C5 C4 H4 . . 119.6 ?
    C3 C4 H4 . . 119.6 ?
    O3 C6 C7 . . 122.0(3) ?
    O3 C6 C5 . . 116.7(4) ?
    C7 C6 C5 . . 121.4(4) ?
    O4 C9 O3 . . 115.3(4) ?
    O4 C9 C8 . . 127.5(4) ?
    O3 C9 C8 . . 117.3(3) ?
    C15 C16 C17 . . 120.0(4) ?
    C15 C16 H10 . . 120.0 ?
    C17 C16 H10 . . 120.0 ?
    C4 C5 C6 . . 119.4(4) ?
    C4 C5 H5 . . 120.3 ?
    C6 C5 H5 . . 120.3 ?
    C6 O3 C9 . . 122.9(3) ?
    C16 C17 C18 . . 119.5(5) ?
    C16 C17 H9 . . 120.3 ?
    C18 C17 H9 . . 120.3 ?
    C13 C18 C17 . . 121.4(4) ?
    C13 C18 H8 . . 119.3 ?
    C17 C18 H8 . . 119.3 ?
    C18 C13 C14 . . 118.5(4) ?
    C18 C13 C12 . . 122.1(4) ?
    C14 C13 C12 . . 119.3(4) ?
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
    C5 H5 O3 2_655 0.93 2.57 3.350(5) 142.4
    O1 H2 O2 . 0.99(7) 1.51(7) 2.413(4) 149(6)
data_global
_journal_date_recd_electronic     2011-06-21
_journal_date_accepted     2011-07-22
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2011
_journal_volume     67
_journal_issue      8
_journal_page_first     o2209
_journal_page_last     o2209
_journal_paper_category     QO
_journal_coeditor_code     CV5125
_publ_contact_author_name     'Ben Hassen, Rached'
_publ_contact_author_address
;
Unit\'e de chimie des Mat\'eriaux,
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
;
4-Hydroxy-3-[(<i>E</i>)-3-phenylprop-2-enoyl]-2<i>H</i>-chromen-2-one
;
loop_
    _publ_author_name
    _publ_author_address
    'Ghouili, Afef'
;
Unit\'e de chimie des Mat\'eriaux,
ISSBAT, Universit\'e de Tunis-ElManar,
9 Avenue Dr Zoheir SAFI, 1006 Tunis, Tunisia
;
    'Ben Hassen, Rached'
;
Unit\'e de chimie des Mat\'eriaux,
ISSBAT, Universit\'e de Tunis-ElManar,
9 Avenue Dr Zoheir SAFI, 1006 Tunis, Tunisia
;