##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# 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.                                        #
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# 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 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
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data_global
_audit_creation_method     SHELXL-97
_journal_data_validation_number     ?
_journal_date_recd_electronic     2010-10-29
_journal_date_accepted     2010-11-03
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue     12
_journal_page_first     o3122
_journal_page_last     o3122
_journal_paper_category     QO
_journal_coeditor_code     XU5076
_publ_contact_author_name     'Professor Jerzy Błażejowski'
_publ_contact_author_address
;
University of Gdańsk
Faculty of Chemistry
J. Sobieskiego 18
80-952 Gdańsk
Poland
;
_publ_contact_author_email     'bla@chem.univ.gda.pl'
_publ_contact_author_fax     '+48 58 523 53 57'
_publ_contact_author_phone     '+48 58 523 53 31'
_publ_section_title
;
2-(4-Fluorophenyl)-3-hydroxy-4H-chromen-4-one
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Wera, Michał' ?
;
Faculty of Chemistry,
University of Gdańsk,
J. Sobieskiego 18,
80-952 Gdańsk
Poland
;
    'Serdiuk, Ilia E.' ?
;
Institute of Chemistry
V.N. Karazin National University
Svobody 4
61077 Kharkiv
Ukraine
;
    'Roshal, Alexander D.' ?
;
Institute of Chemistry
V.N. Karazin National University
Svobody 4
61077 Kharkiv
Ukraine
;
    'Błażejowski, Jerzy' ?
;
Faculty of Chemistry,
University of Gdańsk,
J. Sobieskiego 18,
80-952 Gdańsk
Poland
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
2-(4-Fluorophenyl)-3-hydroxy-4H-chromen-4-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C15 H9 F O3'
_chemical_formula_sum     'C15 H9 F O3'
_chemical_formula_iupac     'C15 H9 F O3'
_chemical_formula_weight     256.22
_chemical_melting_point     ?
_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     15.5971(9)
_cell_length_b     3.8790(2)
_cell_length_c     19.1655(12)
_cell_angle_alpha     90.00
_cell_angle_beta     103.906(6)
_cell_angle_gamma     90.00
_cell_volume     1125.55(11)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1729
_cell_measurement_theta_min     3.86
_cell_measurement_theta_max     25.05
_cell_measurement_temperature     295(2)
_exptl_crystal_description     'plate'
_exptl_crystal_colour     'yellow'
_exptl_crystal_size_max     0.6
_exptl_crystal_size_mid     0.4
_exptl_crystal_size_min     0.05
_exptl_crystal_density_diffrn     1.512
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     528
_exptl_absorpt_coefficient_mu     0.116
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2008)
;
_exptl_absorpt_correction_T_min     0.956
_exptl_absorpt_correction_T_max     0.991
_exptl_special_details
;
;
_diffrn_ambient_temperature     295(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Oxford Diffraction Gemini R Ultra Ruby CCD'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     10.4002
_diffrn_reflns_number     7973
_diffrn_reflns_av_R_equivalents     0.0258
_diffrn_reflns_av_sigmaI/netI     0.0168
_diffrn_reflns_theta_min     3.86
_diffrn_reflns_theta_max     25.05
_diffrn_reflns_theta_full     25.05
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -18
_diffrn_reflns_limit_h_max     14
_diffrn_reflns_limit_k_min     -4
_diffrn_reflns_limit_k_max     4
_diffrn_reflns_limit_l_min     -20
_diffrn_reflns_limit_l_max     22
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     1999
_reflns_number_gt     1729
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0595
_refine_ls_R_factor_gt     0.0499
_refine_ls_wR_factor_gt     0.1086
_refine_ls_wR_factor_ref     0.1133
_refine_ls_goodness_of_fit_ref     1.122
_refine_ls_restrained_S_all     1.122
_refine_ls_number_reflns     1999
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0392P)²+0.8330P] 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     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.207
_refine_diff_density_min     -0.211
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.010(2)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
    'F' 'F' 0.0171 0.0103
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CrysAlis CCD (Oxford Diffraction, 2008)'
_computing_cell_refinement     'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_data_reduction     'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
              'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
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
    O O1 0.78326(8) 0.9690(4) 0.42669(7) 0.0375(4) Uani d . 1 . .
    C C2 0.75381(12) 0.8861(5) 0.48666(10) 0.0305(5) Uani d . 1 . .
    C C3 0.66843(13) 0.9437(6) 0.48778(10) 0.0340(5) Uani d . 1 . .
    C C4 0.60607(13) 1.0994(6) 0.42768(11) 0.0350(5) Uani d . 1 . .
    C C5 0.58939(13) 1.3469(6) 0.30419(11) 0.0376(5) Uani d . 1 . .
    H H5 0.5310 1.4047 0.3022 0.045 Uiso calc R 1 . .
    C C6 0.62406(14) 1.4144(6) 0.24658(12) 0.0421(6) Uani d . 1 . .
    H H6 0.5891 1.5134 0.2052 0.051 Uiso calc R 1 . .
    C C7 0.71196(15) 1.3346(7) 0.25000(12) 0.0442(6) Uani d . 1 . .
    H H7 0.7354 1.3816 0.2108 0.053 Uiso calc R 1 . .
    C C8 0.76441(14) 1.1878(7) 0.31031(11) 0.0423(6) Uani d . 1 . .
    H H8 0.8232 1.1364 0.3124 0.051 Uiso calc R 1 . .
    C C9 0.64095(12) 1.1912(5) 0.36633(10) 0.0306(5) Uani d . 1 . .
    C C10 0.72829(12) 1.1169(6) 0.36824(10) 0.0320(5) Uani d . 1 . .
    O O11 0.63946(10) 0.8624(5) 0.54678(8) 0.0542(5) Uani d . 1 . .
    H H11 0.585(2) 0.891(9) 0.5380(16) 0.081 Uiso d . 1 . .
    O O12 0.52826(9) 1.1478(5) 0.42954(9) 0.0554(5) Uani d . 1 . .
    C C13 0.82586(12) 0.7435(5) 0.54311(10) 0.0306(5) Uani d . 1 . .
    C C14 0.91251(13) 0.7678(6) 0.53545(11) 0.0389(5) Uani d . 1 . .
    H H14 0.9230 0.8692 0.4943 0.047 Uiso calc R 1 . .
    C C15 0.98280(14) 0.6447(6) 0.58754(11) 0.0420(6) Uani d . 1 . .
    H H15 1.0402 0.6623 0.5818 0.050 Uiso calc R 1 . .
    C C16 0.96660(13) 0.4969(6) 0.64746(11) 0.0369(5) Uani d . 1 . .
    C C17 0.88298(14) 0.4651(6) 0.65736(11) 0.0406(6) Uani d . 1 . .
    H H17 0.8736 0.3620 0.6987 0.049 Uiso calc R 1 . .
    C C18 0.81276(13) 0.5880(6) 0.60519(11) 0.0366(5) Uani d . 1 . .
    H H18 0.7557 0.5667 0.6116 0.044 Uiso calc R 1 . .
    F F19 1.03595(8) 0.3745(4) 0.69849(7) 0.0561(4) Uani 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
    O1 0.0255(7) 0.0598(10) 0.0287(7) 0.0049(7) 0.0097(6) 0.0056(7)
    C2 0.0284(10) 0.0368(12) 0.0278(10) -0.0038(9) 0.0098(8) -0.0027(9)
    C3 0.0294(10) 0.0435(12) 0.0310(10) -0.0026(10) 0.0109(8) -0.0009(10)
    C4 0.0262(10) 0.0423(12) 0.0375(11) -0.0016(9) 0.0095(9) -0.0022(10)
    C5 0.0281(10) 0.0424(13) 0.0409(12) 0.0012(9) 0.0053(9) 0.0008(10)
    C6 0.0402(12) 0.0492(14) 0.0346(11) 0.0048(11) 0.0043(9) 0.0049(11)
    C7 0.0427(12) 0.0580(15) 0.0343(11) 0.0027(11) 0.0140(10) 0.0054(11)
    C8 0.0314(11) 0.0615(16) 0.0363(11) 0.0035(11) 0.0129(9) 0.0020(11)
    C9 0.0265(10) 0.0340(11) 0.0314(10) -0.0030(9) 0.0068(8) -0.0043(9)
    C10 0.0263(10) 0.0402(12) 0.0284(10) -0.0014(9) 0.0045(8) -0.0028(9)
    O11 0.0303(8) 0.0941(15) 0.0432(9) 0.0096(9) 0.0185(7) 0.0201(9)
    O12 0.0274(8) 0.0902(14) 0.0523(10) 0.0100(9) 0.0169(7) 0.0174(10)
    C13 0.0280(10) 0.0351(11) 0.0292(10) -0.0022(9) 0.0081(8) -0.0043(9)
    C14 0.0331(11) 0.0515(14) 0.0342(11) -0.0001(10) 0.0122(9) 0.0077(10)
    C15 0.0267(10) 0.0566(15) 0.0429(12) -0.0002(10) 0.0090(9) 0.0054(11)
    C16 0.0327(11) 0.0424(13) 0.0320(11) 0.0020(10) 0.0010(9) 0.0002(10)
    C17 0.0392(12) 0.0537(15) 0.0302(11) -0.0035(11) 0.0109(9) 0.0040(10)
    C18 0.0287(10) 0.0497(13) 0.0328(11) -0.0027(10) 0.0100(8) 0.0006(10)
    F19 0.0386(7) 0.0798(11) 0.0443(8) 0.0069(7) -0.0013(6) 0.0139(7)
_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 C10 . 1.363(2) ?
    O1 C2 . 1.374(2) ?
    C2 C3 . 1.355(3) ?
    C2 C13 . 1.468(3) ?
    C3 O11 . 1.352(2) ?
    C3 C4 . 1.449(3) ?
    C4 O12 . 1.237(2) ?
    C4 C9 . 1.454(3) ?
    C5 C6 . 1.367(3) ?
    C5 C9 . 1.403(3) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.392(3) ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.369(3) ?
    C7 H7 . 0.9300 ?
    C8 C10 . 1.388(3) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.384(3) ?
    O11 H11 . 0.83(3) ?
    C13 C18 . 1.392(3) ?
    C13 C14 . 1.397(3) ?
    C14 C15 . 1.379(3) ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.360(3) ?
    C15 H15 . 0.9300 ?
    C16 F19 . 1.358(2) ?
    C16 C17 . 1.368(3) ?
    C17 C18 . 1.378(3) ?
    C17 H17 . 0.9300 ?
    C18 H18 . 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
    C10 O1 C2 . . 121.01(15) ?
    C3 C2 O1 . . 120.12(18) ?
    C3 C2 C13 . . 129.15(18) ?
    O1 C2 C13 . . 110.73(16) ?
    O11 C3 C2 . . 120.13(19) ?
    O11 C3 C4 . . 117.82(17) ?
    C2 C3 C4 . . 122.04(18) ?
    O12 C4 C3 . . 121.08(19) ?
    O12 C4 C9 . . 123.13(19) ?
    C3 C4 C9 . . 115.79(17) ?
    C6 C5 C9 . . 120.73(19) ?
    C6 C5 H5 . . 119.6 ?
    C9 C5 H5 . . 119.6 ?
    C5 C6 C7 . . 119.7(2) ?
    C5 C6 H6 . . 120.1 ?
    C7 C6 H6 . . 120.1 ?
    C8 C7 C6 . . 120.9(2) ?
    C8 C7 H7 . . 119.5 ?
    C6 C7 H7 . . 119.5 ?
    C7 C8 C10 . . 118.86(19) ?
    C7 C8 H8 . . 120.6 ?
    C10 C8 H8 . . 120.6 ?
    C10 C9 C5 . . 118.14(18) ?
    C10 C9 C4 . . 119.01(18) ?
    C5 C9 C4 . . 122.85(18) ?
    O1 C10 C9 . . 122.00(17) ?
    O1 C10 C8 . . 116.41(17) ?
    C9 C10 C8 . . 121.58(19) ?
    C3 O11 H11 . . 109(2) ?
    C18 C13 C14 . . 117.60(18) ?
    C18 C13 C2 . . 123.34(17) ?
    C14 C13 C2 . . 119.05(18) ?
    C15 C14 C13 . . 121.43(19) ?
    C15 C14 H14 . . 119.3 ?
    C13 C14 H14 . . 119.3 ?
    C16 C15 C14 . . 118.73(19) ?
    C16 C15 H15 . . 120.6 ?
    C14 C15 H15 . . 120.6 ?
    F19 C16 C15 . . 118.55(19) ?
    F19 C16 C17 . . 119.32(19) ?
    C15 C16 C17 . . 122.1(2) ?
    C16 C17 C18 . . 119.08(19) ?
    C16 C17 H17 . . 120.5 ?
    C18 C17 H17 . . 120.5 ?
    C17 C18 C13 . . 121.04(18) ?
    C17 C18 H18 . . 119.5 ?
    C13 C18 H18 . . 119.5 ?
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
    C10 O1 C2 C3 . . . . 1.5(3) ?
    C10 O1 C2 C13 . . . . -177.75(18) ?
    O1 C2 C3 O11 . . . . -179.95(19) ?
    C13 C2 C3 O11 . . . . -0.8(4) ?
    O1 C2 C3 C4 . . . . -1.4(3) ?
    C13 C2 C3 C4 . . . . 177.7(2) ?
    O11 C3 C4 O12 . . . . -1.9(3) ?
    C2 C3 C4 O12 . . . . 179.5(2) ?
    O11 C3 C4 C9 . . . . 178.3(2) ?
    C2 C3 C4 C9 . . . . -0.3(3) ?
    C9 C5 C6 C7 . . . . -1.3(4) ?
    C5 C6 C7 C8 . . . . 0.2(4) ?
    C6 C7 C8 C10 . . . . 0.4(4) ?
    C6 C5 C9 C10 . . . . 1.7(3) ?
    C6 C5 C9 C4 . . . . -177.0(2) ?
    O12 C4 C9 C10 . . . . -177.9(2) ?
    C3 C4 C9 C10 . . . . 1.9(3) ?
    O12 C4 C9 C5 . . . . 0.8(4) ?
    C3 C4 C9 C5 . . . . -179.4(2) ?
    C2 O1 C10 C9 . . . . 0.2(3) ?
    C2 O1 C10 C8 . . . . -179.50(19) ?
    C5 C9 C10 O1 . . . . 179.34(19) ?
    C4 C9 C10 O1 . . . . -1.9(3) ?
    C5 C9 C10 C8 . . . . -1.0(3) ?
    C4 C9 C10 C8 . . . . 177.8(2) ?
    C7 C8 C10 O1 . . . . 179.6(2) ?
    C7 C8 C10 C9 . . . . 0.0(4) ?
    C3 C2 C13 C18 . . . . 11.1(4) ?
    O1 C2 C13 C18 . . . . -169.68(19) ?
    C3 C2 C13 C14 . . . . -167.8(2) ?
    O1 C2 C13 C14 . . . . 11.4(3) ?
    C18 C13 C14 C15 . . . . -0.4(3) ?
    C2 C13 C14 C15 . . . . 178.6(2) ?
    C13 C14 C15 C16 . . . . 0.0(4) ?
    C14 C15 C16 F19 . . . . 179.7(2) ?
    C14 C15 C16 C17 . . . . 0.4(4) ?
    F19 C16 C17 C18 . . . . -179.6(2) ?
    C15 C16 C17 C18 . . . . -0.3(4) ?
    C16 C17 C18 C13 . . . . -0.1(4) ?
    C14 C13 C18 C17 . . . . 0.5(3) ?
    C2 C13 C18 C17 . . . . -178.5(2) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_D
    _geom_hbond_site_symmetry_H
    _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
    O11 H11 O12 1_555 1_555 1_555 0.83(3) 2.28(3) 2.722(2) 113(3) y
    O11 H11 O12 1_555 1_555 3_676 0.83(3) 2.02(3) 2.761(2) 149(3) y
