##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# 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.                                        #
#                                                                            #
# 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  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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# This file may be used for bona fide research purposes within the           #
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data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
8-Benzoyl-7-hydroxy-4-methyl-2<i>H</i>-1-benzopyran-2-one monohydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C17 H12 O4, H2 O'
_chemical_formula_sum     'C17 H14 O5'
_chemical_formula_iupac     'C17 H12 O4, H2 O'
_chemical_formula_weight     298.28
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'C 2/c'
_symmetry_space_group_name_Hall     '-C 2yc'
loop_
    _symmetry_equiv_pos_as_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'
_cell_length_a     14.8912(15)
_cell_length_b     9.6768(11)
_cell_length_c     20.644(2)
_cell_angle_alpha     90.00
_cell_angle_beta     104.275(2)
_cell_angle_gamma     90.00
_cell_volume     2882.9(5)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     2106
_cell_measurement_theta_min     2.598
_cell_measurement_theta_max     26.252
_cell_measurement_temperature     298(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.49
_exptl_crystal_size_mid     0.24
_exptl_crystal_size_min     0.21
_exptl_crystal_density_diffrn     1.374
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1248
_exptl_absorpt_coefficient_mu     0.102
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.9518
_exptl_absorpt_correction_T_max     0.9789
_exptl_special_details
;
;
_diffrn_ambient_temperature     298(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     7271
_diffrn_reflns_av_R_equivalents     0.0363
_diffrn_reflns_av_sigmaI/netI     0.0383
_diffrn_reflns_theta_min     2.04
_diffrn_reflns_theta_max     25.01
_diffrn_reflns_theta_full     25.01
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -17
_diffrn_reflns_limit_h_max     14
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -24
_diffrn_reflns_limit_l_max     24
_diffrn_standards_number     0
_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     2549
_reflns_number_gt     1706
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0714
_refine_ls_R_factor_gt     0.0404
_refine_ls_wR_factor_gt     0.0858
_refine_ls_wR_factor_ref     0.1104
_refine_ls_goodness_of_fit_ref     1.050
_refine_ls_restrained_S_all     1.050
_refine_ls_number_reflns     2549
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[\s^2^(Fo^2^)+(0.0463P)^2^+1.1970P] 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     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.147
_refine_diff_density_min     -0.193
_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 (Siemens, 1996)'
_computing_cell_refinement     'SAINT (Siemens, 1996)'
_computing_data_reduction     'SAINT (Siemens, 1996)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
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 0.17438(9) 0.30443(14) 0.31197(6) 0.0429(4) Uani d . 1 . .
    O O2 0.13299(12) 0.09551(16) 0.27504(8) 0.0590(5) Uani d . 1 . .
    O O3 0.27345(10) 0.73405(18) 0.40667(7) 0.0516(4) Uani d . 1 . .
    H H3 0.2699(19) 0.830(3) 0.4027(13) 0.093(10) Uiso d . 1 . .
    O O4 0.23351(10) 0.42720(19) 0.46551(7) 0.0621(5) Uani d . 1 . .
    C C1 0.12717(15) 0.2185(2) 0.26211(10) 0.0443(5) Uani d . 1 . .
    C C2 0.07607(15) 0.2814(2) 0.20096(10) 0.0453(6) Uani d . 1 . .
    H H2 0.0427(14) 0.218(2) 0.1671(10) 0.050(6) Uiso d . 1 . .
    C C3 0.07320(13) 0.4192(2) 0.19106(9) 0.0397(5) Uani d . 1 . .
    C C4 0.12370(13) 0.5072(2) 0.24429(9) 0.0367(5) Uani d . 1 . .
    C C5 0.12629(15) 0.6515(2) 0.24161(11) 0.0436(5) Uani d . 1 . .
    H H5 0.0918(13) 0.697(2) 0.2017(10) 0.042(5) Uiso d . 1 . .
    C C6 0.17489(14) 0.7290(2) 0.29421(11) 0.0438(5) Uani d . 1 . .
    H H6 0.1748(14) 0.829(2) 0.2898(10) 0.050(6) Uiso d . 1 . .
    C C7 0.22368(14) 0.6637(2) 0.35315(10) 0.0395(5) Uani d . 1 . .
    C C8 0.22316(13) 0.5202(2) 0.35827(9) 0.0364(5) Uani d . 1 . .
    C C9 0.17343(13) 0.4459(2) 0.30380(9) 0.0359(5) Uani d . 1 . .
    C C10 0.01805(19) 0.4821(3) 0.12713(12) 0.0522(6) Uani d . 1 . .
    H H10A -0.0231(17) 0.414(3) 0.0985(12) 0.074(8) Uiso d . 1 . .
    H H10B -0.0219(17) 0.555(3) 0.1356(12) 0.071(8) Uiso d . 1 . .
    H H10C 0.0575(16) 0.525(3) 0.1039(12) 0.064(8) Uiso d . 1 . .
    C C11 0.27364(14) 0.4473(2) 0.42133(9) 0.0390(5) Uani d . 1 . .
    C C12 0.37057(13) 0.4036(2) 0.42734(9) 0.0360(5) Uani d . 1 . .
    H H13 0.3868(14) 0.308(2) 0.5173(11) 0.056(7) Uiso d . 1 . .
    C C13 0.41872(16) 0.3316(2) 0.48382(11) 0.0484(6) Uani d . 1 . .
    C C14 0.51066(17) 0.2977(3) 0.49076(13) 0.0568(7) Uani d . 1 . .
    H H14 0.5453(14) 0.250(2) 0.5300(11) 0.057(6) Uiso d . 1 . .
    C C15 0.55516(17) 0.3334(3) 0.44212(12) 0.0552(6) Uani d . 1 . .
    H H15 0.6208(17) 0.309(2) 0.4484(11) 0.063(7) Uiso d . 1 . .
    C C16 0.50801(16) 0.4022(3) 0.38535(12) 0.0523(6) Uani d . 1 . .
    H H16 0.5390(16) 0.430(2) 0.3503(12) 0.070(7) Uiso d . 1 . .
    C C17 0.41556(15) 0.4371(2) 0.37787(10) 0.0417(5) Uani d . 1 . .
    H H17 0.3830(13) 0.483(2) 0.3384(10) 0.046(6) Uiso d . 1 . .
    O O5 0.25946(14) 0.00677(18) 0.39756(10) 0.0631(5) Uani d . 1 . .
    H H5A 0.220(2) 0.049(4) 0.3623(17) 0.125(13) Uiso d . 1 . .
    H H5B 0.258(2) 0.045(3) 0.4355(16) 0.101(11) Uiso 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 0.0533(9) 0.0359(9) 0.0360(8) 0.0039(7) 0.0042(6) 0.0021(6)
    O2 0.0815(12) 0.0410(10) 0.0500(9) 0.0009(9) 0.0076(8) 0.0008(8)
    O3 0.0539(10) 0.0458(11) 0.0477(9) -0.0017(8) -0.0015(7) -0.0047(8)
    O4 0.0535(10) 0.0921(13) 0.0436(9) 0.0117(9) 0.0173(8) 0.0148(8)
    C1 0.0524(14) 0.0411(14) 0.0403(12) 0.0011(11) 0.0133(10) -0.0015(10)
    C2 0.0499(14) 0.0491(15) 0.0357(12) -0.0010(11) 0.0086(10) -0.0057(10)
    C3 0.0376(12) 0.0496(14) 0.0324(10) 0.0032(10) 0.0095(9) 0.0010(10)
    C4 0.0360(11) 0.0409(13) 0.0327(10) 0.0051(9) 0.0078(9) 0.0034(9)
    C5 0.0431(13) 0.0445(14) 0.0393(12) 0.0072(11) 0.0031(10) 0.0094(11)
    C6 0.0454(13) 0.0354(13) 0.0479(13) 0.0045(10) 0.0065(10) 0.0046(10)
    C7 0.0366(12) 0.0425(13) 0.0383(11) 0.0014(10) 0.0074(9) -0.0020(10)
    C8 0.0351(11) 0.0401(13) 0.0339(10) 0.0035(9) 0.0080(9) 0.0017(9)
    C9 0.0373(11) 0.0340(12) 0.0374(11) 0.0049(9) 0.0108(9) 0.0027(9)
    C10 0.0494(15) 0.0626(18) 0.0403(13) 0.0049(14) 0.0029(12) 0.0046(12)
    C11 0.0427(12) 0.0404(12) 0.0329(11) -0.0018(10) 0.0076(9) -0.0017(9)
    C12 0.0390(11) 0.0333(12) 0.0329(10) -0.0020(9) 0.0039(9) -0.0018(9)
    C13 0.0480(14) 0.0536(15) 0.0419(12) 0.0010(11) 0.0079(11) 0.0088(11)
    C14 0.0501(15) 0.0607(17) 0.0526(15) 0.0086(12) -0.0007(12) 0.0109(12)
    C15 0.0391(14) 0.0596(16) 0.0636(16) 0.0030(12) 0.0064(12) -0.0049(13)
    C16 0.0473(14) 0.0588(16) 0.0534(14) -0.0038(12) 0.0176(12) -0.0056(12)
    C17 0.0464(13) 0.0402(13) 0.0363(11) -0.0016(10) 0.0065(10) 0.0000(10)
    O5 0.0828(13) 0.0548(12) 0.0488(11) 0.0045(9) 0.0106(10) -0.0027(9)
_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 C1 . 1.374(2) ?
    O1 C9 . 1.379(2) ?
    O2 C1 . 1.218(2) ?
    O3 C7 . 1.352(2) ?
    O3 H3 . 0.93(3) ?
    O4 C11 . 1.223(2) ?
    C1 C2 . 1.438(3) ?
    C2 C3 . 1.348(3) ?
    C2 H2 . 0.97(2) ?
    C3 C4 . 1.446(3) ?
    C3 C10 . 1.501(3) ?
    C4 C5 . 1.398(3) ?
    C4 C9 . 1.400(3) ?
    C5 C6 . 1.370(3) ?
    C5 H5 . 0.96(2) ?
    C6 C7 . 1.404(3) ?
    C6 H6 . 0.97(2) ?
    C7 C8 . 1.393(3) ?
    C8 C9 . 1.385(3) ?
    C8 C11 . 1.509(3) ?
    C10 H10A . 0.99(3) ?
    C10 H10B . 0.96(3) ?
    C10 H10C . 0.94(2) ?
    C11 C12 . 1.479(3) ?
    C12 C17 . 1.391(3) ?
    C12 C13 . 1.395(3) ?
    C13 C14 . 1.381(3) ?
    C13 H13 . 0.96(2) ?
    C14 C15 . 1.376(3) ?
    C14 H14 . 0.96(2) ?
    C15 C16 . 1.380(3) ?
    C15 H15 . 0.98(2) ?
    C16 C17 . 1.389(3) ?
    C16 H16 . 0.99(2) ?
    C17 H17 . 0.95(2) ?
    O5 H5A . 0.91(4) ?
    O5 H5B . 0.87(3) ?
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
    C1 O1 C9 . . 121.41(15) ?
    C7 O3 H3 . . 114.9(17) ?
    O2 C1 O1 . . 115.56(19) ?
    O2 C1 C2 . . 126.8(2) ?
    O1 C1 C2 . . 117.6(2) ?
    C3 C2 C1 . . 122.8(2) ?
    C3 C2 H2 . . 121.6(12) ?
    C1 C2 H2 . . 115.7(12) ?
    C2 C3 C4 . . 118.45(18) ?
    C2 C3 C10 . . 121.6(2) ?
    C4 C3 C10 . . 119.9(2) ?
    C5 C4 C9 . . 116.35(19) ?
    C5 C4 C3 . . 124.92(19) ?
    C9 C4 C3 . . 118.73(19) ?
    C6 C5 C4 . . 122.0(2) ?
    C6 C5 H5 . . 119.5(12) ?
    C4 C5 H5 . . 118.5(12) ?
    C5 C6 C7 . . 120.0(2) ?
    C5 C6 H6 . . 118.9(12) ?
    C7 C6 H6 . . 121.1(12) ?
    O3 C7 C8 . . 116.86(18) ?
    O3 C7 C6 . . 123.0(2) ?
    C8 C7 C6 . . 120.16(19) ?
    C9 C8 C7 . . 117.90(18) ?
    C9 C8 C11 . . 120.69(19) ?
    C7 C8 C11 . . 121.40(18) ?
    O1 C9 C8 . . 115.39(16) ?
    O1 C9 C4 . . 121.00(17) ?
    C8 C9 C4 . . 123.60(19) ?
    C3 C10 H10A . . 112.3(14) ?
    C3 C10 H10B . . 111.4(15) ?
    H10A C10 H10B . . 106(2) ?
    C3 C10 H10C . . 110.6(14) ?
    H10A C10 H10C . . 111(2) ?
    H10B C10 H10C . . 105(2) ?
    O4 C11 C12 . . 122.57(18) ?
    O4 C11 C8 . . 119.13(18) ?
    C12 C11 C8 . . 118.30(16) ?
    C17 C12 C13 . . 119.26(19) ?
    C17 C12 C11 . . 120.57(18) ?
    C13 C12 C11 . . 120.15(17) ?
    C14 C13 C12 . . 119.8(2) ?
    C14 C13 H13 . . 121.6(13) ?
    C12 C13 H13 . . 118.6(13) ?
    C15 C14 C13 . . 120.5(2) ?
    C15 C14 H14 . . 118.6(12) ?
    C13 C14 H14 . . 120.8(12) ?
    C14 C15 C16 . . 120.3(2) ?
    C14 C15 H15 . . 119.2(13) ?
    C16 C15 H15 . . 120.5(13) ?
    C15 C16 C17 . . 119.7(2) ?
    C15 C16 H16 . . 121.4(14) ?
    C17 C16 H16 . . 118.9(14) ?
    C16 C17 C12 . . 120.4(2) ?
    C16 C17 H17 . . 119.5(12) ?
    C12 C17 H17 . . 120.1(12) ?
    H5A O5 H5B . . 112(3) ?
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
    O3 H3 O5 1_565 0.93(3) 1.72(3) 2.650(2) 177(3)
    O5 H5A O2 . 0.91(4) 2.00(4) 2.887(3) 166(3)
    O5 H5B O4 7_556 0.87(3) 2.03(3) 2.875(2) 162(3)
    C17 H17 O2 4_555 0.95(2) 2.54(2) 3.422(3) 154.7(16)
data_global
_journal_date_recd_electronic     2010-11-08
_journal_date_accepted     2010-11-10
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue     12
_journal_page_first     o3183
_journal_page_last     o3183
_journal_paper_category     QO
_journal_coeditor_code     XU5087
_publ_contact_author_name     'Shu-Ping Yang'
_publ_contact_author_address
;
College of Chemical Engineering
Huaihai Institute of Technology
Lianyungang 222005
People's Republic of China
;
_publ_contact_author_email     'spyang69320@yahoo.cn'
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
8-Benzoyl-7-hydroxy-4-methyl-2<i>H</i>-1-benzopyran-2-one monohydrate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Yang, Shu-Ping' .
;
College of Chemical Engineering
Huaihai Institute of Technology
Lianyungang 222005
People's Republic of China
;
    'Han, Li-Jun' .
;
College of Mathematics and Science
Huaihai Institute of Technology
Lianyungang 222005
People's Republic of China
;
    'Wang, Da-Qi' .
;
College of Chemistry and Chemical Engineering
Liaocheng University
Shandong 252059
People's Republic of China
;
    'Chen, Xiao-Yun' .
;
College of Chemical Engineering
Huaihai Institute of Technology
Lianyungang 222005
People's Republic of China
;