##############################################################################
###                                                                        ###
###        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 2.1.    #
#                                                                            #
# 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/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2003-12-03
_journal_date_accepted     2003-12-22
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2004
_journal_volume     60
_journal_issue      2
_journal_page_first     o168
_journal_page_last     o169
_journal_paper_category     EO
_publ_contact_author_name     'Dr. Zhifang YU'
_publ_contact_author_address
; Department of Chemistry,Tianjin University
   Tianjin 300072
   People's Republic of China
;
_publ_contact_author_email     zhifang@public.tpt.tj.cn
_publ_contact_author_fax     ?
_publ_contact_author_phone     '86 022 27406034'
_publ_section_title
;
3-(2,4-Dichlorophenyl)-1-(2-furyl)-3-hydroxypropan-1-one
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Yu*, Zhifang' .
; Department of Chemistry, Tianjin University
   Tianjin 300072
   People's Repulic of China
;
    'Gu, Xiuyan' .
; Department of Chemistry, Tianjin University
   Tianjin 300072
   People's Repulic of China
;
    'Zhao, Bing' .
; Department of Chemistry, Tianjin University
   Tianjin 300072
   People's Repulic of China
;
    'Cao, Xiaoqiang' .
; Department of Chemistry, Tianjin University
   Tianjin 300072
   People's Repulic of China
;
data_I
_chemical_name_systematic
;
3-(2,4-Dichlorophenyl)-1-(2-furyl)-3-hydroxypropan-1-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H10 Cl2 O3'
_chemical_formula_sum     'C13 H10 Cl2 O3'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac     'C13 H10 Cl2 O3'
_chemical_formula_weight     285.11
_chemical_melting_point     340
_symmetry_cell_setting     Triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     7.933(2)
_cell_length_b     8.737(3)
_cell_length_c     9.907(3)
_cell_angle_alpha     79.464(4)
_cell_angle_beta     72.596(4)
_cell_angle_gamma     79.918(5)
_cell_volume     638.9(3)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     989
_cell_measurement_theta_min     2.71
_cell_measurement_theta_max     26.28
_cell_measurement_temperature     293(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.22
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.14
_exptl_crystal_density_diffrn     1.482
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     292
_exptl_absorpt_coefficient_mu     0.504
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.882
_exptl_absorpt_correction_T_max     0.932
_exptl_special_details
;
  ?
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     'Mo K\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     'ψ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     3322
_diffrn_reflns_av_R_equivalents     0.0158
_diffrn_reflns_av_sigmaI/netI     0.0272
_diffrn_reflns_theta_min     2.18
_diffrn_reflns_theta_max     25.01
_diffrn_reflns_theta_full     25.01
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -11
_diffrn_reflns_limit_l_max     11
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
loop_
    _diffrn_standard_refln_index_h
    _diffrn_standard_refln_index_k
    _diffrn_standard_refln_index_l
    ? ? ?
_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 > 2sigma(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     2246
_reflns_number_gt     1808
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0498
_refine_ls_R_factor_gt     0.0385
_refine_ls_wR_factor_gt     0.1018
_refine_ls_wR_factor_ref     0.1109
_refine_ls_goodness_of_fit_ref     1.067
_refine_ls_restrained_S_all     1.067
_refine_ls_number_reflns     2246
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
          'w = 1/[σ²(Fo²)+(0.0554P)²+0.1932P] 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     0.004
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.324
_refine_diff_density_min     -0.438
_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
;
    Cl Cl 0.1484 0.1585
; 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, 1997) '
_computing_cell_refinement     'SMART'
_computing_data_reduction     'SMART'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Bruker, 1997)'
_computing_publication_material     'SHELXTL'
loop_
    _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
    _atom_site_type_symbol
    Cl1 0.43230(8) 0.14544(9) 0.77489(7) 0.0706(3) Uani d . 1 . . Cl
    Cl2 -0.17314(9) -0.08303(9) 0.84055(8) 0.0758(3) Uani d . 1 . . Cl
    O1 0.3100(2) 0.46997(19) 0.41418(17) 0.0588(4) Uani d . 1 . . O
    H1 0.2657 0.5367 0.4675 0.088 Uiso calc R 1 . . H
    O2 0.7640(2) 0.3692(2) 0.34604(18) 0.0656(5) Uani d . 1 . . O
    O3 0.8364(2) 0.4239(2) 0.05729(18) 0.0687(5) Uani d . 1 . . O
    C1 0.0880(3) 0.2283(3) 0.5397(2) 0.0512(6) Uani d . 1 . . C
    H1A 0.0737 0.2896 0.4557 0.061 Uiso calc R 1 . . H
    C2 -0.0390(3) 0.1325(3) 0.6170(2) 0.0535(6) Uani d . 1 . . C
    H2 -0.1371 0.1285 0.5854 0.064 Uiso calc R 1 . . H
    C3 -0.0178(3) 0.0426(3) 0.7423(2) 0.0483(5) Uani d . 1 . . C
    C4 0.1239(3) 0.0486(3) 0.7919(2) 0.0466(5) Uani d . 1 . . C
    H4 0.1356 -0.0109 0.8774 0.056 Uiso calc R 1 . . H
    C5 0.2496(3) 0.1456(3) 0.7117(2) 0.0436(5) Uani d . 1 . . C
    C6 0.2371(3) 0.2358(2) 0.5837(2) 0.0411(5) Uani d . 1 . . C
    C7 0.3811(3) 0.3332(3) 0.4909(2) 0.0460(5) Uani d . 1 . . C
    H7 0.4445 0.3635 0.5510 0.055 Uiso calc R 1 . . H
    C8 0.5123(3) 0.2362(3) 0.3812(2) 0.0569(6) Uani d . 1 . . C
    H8A 0.5584 0.1389 0.4304 0.068 Uiso calc R 1 . . H
    H8B 0.4503 0.2100 0.3194 0.068 Uiso calc R 1 . . H
    C9 0.6662(3) 0.3234(3) 0.2911(2) 0.0499(5) Uani d . 1 . . C
    C10 0.6960(3) 0.3472(3) 0.1375(2) 0.0473(5) Uani d . 1 . . C
    C11 0.6134(3) 0.3081(3) 0.0499(3) 0.0561(6) Uani d . 1 . . C
    H11 0.5142 0.2548 0.0773 0.067 Uiso calc R 1 . . H
    C12 0.7062(4) 0.3635(3) -0.0913(3) 0.0663(7) Uani d . 1 . . C
    H12 0.6802 0.3541 -0.1747 0.080 Uiso calc R 1 . . H
    C13 0.8379(4) 0.4317(4) -0.0811(3) 0.0732(8) Uani d . 1 . . C
    H13 0.9203 0.4788 -0.1586 0.088 Uiso calc R 1 . . H
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
    Cl1 0.0547(4) 0.1037(6) 0.0590(4) -0.0306(3) -0.0275(3) 0.0139(3)
    Cl2 0.0567(4) 0.0902(5) 0.0782(5) -0.0356(4) -0.0115(3) 0.0075(4)
    O1 0.0757(12) 0.0515(9) 0.0461(9) -0.0115(8) -0.0158(8) 0.0025(7)
    O2 0.0646(11) 0.0862(13) 0.0510(10) -0.0243(10) -0.0096(8) -0.0190(9)
    O3 0.0678(11) 0.0902(13) 0.0469(10) -0.0369(10) -0.0017(8) -0.0050(9)
    C1 0.0560(13) 0.0611(14) 0.0385(11) -0.0097(11) -0.0174(10) -0.0021(10)
    C2 0.0459(13) 0.0686(15) 0.0513(13) -0.0121(11) -0.0169(10) -0.0114(11)
    C3 0.0392(11) 0.0540(13) 0.0493(13) -0.0106(10) -0.0058(10) -0.0077(10)
    C4 0.0426(12) 0.0525(13) 0.0406(11) -0.0061(10) -0.0090(9) 0.0001(9)
    C5 0.0381(11) 0.0533(12) 0.0400(11) -0.0065(9) -0.0112(9) -0.0064(9)
    C6 0.0451(11) 0.0448(11) 0.0330(10) -0.0075(9) -0.0074(9) -0.0083(9)
    C7 0.0539(13) 0.0489(12) 0.0350(11) -0.0139(10) -0.0086(9) -0.0048(9)
    C8 0.0634(15) 0.0554(14) 0.0474(13) -0.0200(12) 0.0018(11) -0.0127(11)
    C9 0.0507(13) 0.0507(13) 0.0460(12) -0.0087(10) -0.0045(10) -0.0137(10)
    C10 0.0466(12) 0.0481(12) 0.0439(12) -0.0109(10) -0.0046(10) -0.0063(10)
    C11 0.0556(14) 0.0597(14) 0.0545(14) -0.0095(11) -0.0147(11) -0.0105(11)
    C12 0.0792(19) 0.0743(18) 0.0461(14) -0.0050(15) -0.0202(13) -0.0096(12)
    C13 0.084(2) 0.085(2) 0.0413(14) -0.0208(16) -0.0020(13) -0.0025(13)
_geom_special_details
;
  All esds (except the esd in the dihedral angle between two l.s. planes)
  are estimated using the full covariance matrix.  The cell esds are taken
  into account individually in the estimation of esds in distances, angles
  and torsion angles; correlations between esds in cell parameters are only
  used when they are defined by crystal symmetry.  An approximate (isotropic)
  treatment of cell esds is used for estimating esds 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
    Cl1 C5 . 1.742(2) yes
    Cl2 C3 . 1.743(2) yes
    O1 C7 . 1.418(3) yes
    O1 H1 . 0.8200 ?
    O2 C9 . 1.224(3) yes
    O3 C13 . 1.357(3) ?
    O3 C10 . 1.363(3) ?
    C1 C2 . 1.379(3) ?
    C1 C6 . 1.393(3) ?
    C1 H1A . 0.9300 ?
    C2 C3 . 1.381(3) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.367(3) ?
    C4 C5 . 1.386(3) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.386(3) ?
    C6 C7 . 1.516(3) ?
    C7 C8 . 1.528(3) ?
    C7 H7 . 0.9800 ?
    C8 C9 . 1.514(3) ?
    C8 H8A . 0.9700 ?
    C8 H8B . 0.9700 ?
    C9 C10 . 1.449(3) ?
    C10 C11 . 1.352(3) ?
    C11 C12 . 1.412(4) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.326(4) ?
    C12 H12 . 0.9300 ?
    C13 H13 . 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 H1 . . 109.5 ?
    C13 O3 C10 . . 106.5(2) yes
    C2 C1 C6 . . 121.9(2) ?
    C2 C1 H1A . . 119.0 ?
    C6 C1 H1A . . 119.0 ?
    C1 C2 C3 . . 118.8(2) ?
    C1 C2 H2 . . 120.6 ?
    C3 C2 H2 . . 120.6 ?
    C4 C3 C2 . . 121.6(2) ?
    C4 C3 Cl2 . . 118.45(17) ?
    C2 C3 Cl2 . . 119.98(17) yes
    C3 C4 C5 . . 118.3(2) ?
    C3 C4 H4 . . 120.8 ?
    C5 C4 H4 . . 120.8 ?
    C6 C5 C4 . . 122.57(19) ?
    C6 C5 Cl1 . . 120.29(16) yes
    C4 C5 Cl1 . . 117.11(16) ?
    C5 C6 C1 . . 116.80(19) ?
    C5 C6 C7 . . 122.51(19) ?
    C1 C6 C7 . . 120.63(18) ?
    O1 C7 C6 . . 111.93(18) yes
    O1 C7 C8 . . 107.32(18) ?
    C6 C7 C8 . . 109.40(17) ?
    O1 C7 H7 . . 109.4 ?
    C6 C7 H7 . . 109.4 ?
    C8 C7 H7 . . 109.4 ?
    C9 C8 C7 . . 111.98(18) ?
    C9 C8 H8A . . 109.2 ?
    C7 C8 H8A . . 109.2 ?
    C9 C8 H8B . . 109.2 ?
    C7 C8 H8B . . 109.2 ?
    H8A C8 H8B . . 107.9 ?
    O2 C9 C10 . . 121.3(2) yes
    O2 C9 C8 . . 121.1(2) ?
    C10 C9 C8 . . 117.6(2) ?
    C11 C10 O3 . . 109.1(2) ?
    C11 C10 C9 . . 133.8(2) ?
    O3 C10 C9 . . 117.1(2) yes
    C10 C11 C12 . . 107.1(2) ?
    C10 C11 H11 . . 126.5 ?
    C12 C11 H11 . . 126.5 ?
    C13 C12 C11 . . 106.2(2) ?
    C13 C12 H12 . . 126.9 ?
    C11 C12 H12 . . 126.9 ?
    C12 C13 O3 . . 111.1(2) ?
    C12 C13 H13 . . 124.4 ?
    O3 C13 H13 . . 124.4 ?
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
    C6 C1 C2 C3 . . . . 0.5(4) ?
    C1 C2 C3 C4 . . . . 1.1(4) ?
    C1 C2 C3 Cl2 . . . . -178.54(17) ?
    C2 C3 C4 C5 . . . . -1.3(3) ?
    Cl2 C3 C4 C5 . . . . 178.37(16) ?
    C3 C4 C5 C6 . . . . -0.1(3) ?
    C3 C4 C5 Cl1 . . . . -177.88(17) ?
    C4 C5 C6 C1 . . . . 1.6(3) ?
    Cl1 C5 C6 C1 . . . . 179.31(16) ?
    C4 C5 C6 C7 . . . . -175.64(19) ?
    Cl1 C5 C6 C7 . . . . 2.0(3) ?
    C2 C1 C6 C5 . . . . -1.8(3) ?
    C2 C1 C6 C7 . . . . 175.5(2) ?
    C5 C6 C7 O1 . . . . -149.0(2) yes
    C1 C6 C7 O1 . . . . 33.8(3) ?
    C5 C6 C7 C8 . . . . 92.2(2) ?
    C1 C6 C7 C8 . . . . -85.0(3) ?
    O1 C7 C8 C9 . . . . 62.0(3) yes
    C6 C7 C8 C9 . . . . -176.37(19) ?
    C7 C8 C9 O2 . . . . 58.6(3) yes
    C7 C8 C9 C10 . . . . -122.8(2) ?
    C13 O3 C10 C11 . . . . 0.3(3) ?
    C13 O3 C10 C9 . . . . 179.8(2) ?
    O2 C9 C10 C11 . . . . 178.9(3) yes
    C8 C9 C10 C11 . . . . 0.3(4) ?
    O2 C9 C10 O3 . . . . -0.5(3) ?
    C8 C9 C10 O3 . . . . -179.1(2) ?
    O3 C10 C11 C12 . . . . -0.2(3) ?
    C9 C10 C11 C12 . . . . -179.7(3) ?
    C10 C11 C12 C13 . . . . 0.1(3) ?
    C11 C12 C13 O3 . . . . 0.1(3) ?
    C10 O3 C13 C12 . . . . -0.2(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
    _geom_hbond_publ_flag
    O1 H1 O2 2_666 0.82 2.09 2.839(3) 152 yes
    C7 H7 Cl1 . 0.98 2.64 3.088(2) 108 yes
    C12 H12 O1 2_665 0.93 2.57 3.293(3) 135 yes
