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###                                                                        ###
###        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/  #
# cif/home.html                                                              #
#                                                                            #
# 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.                                        #
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##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(E)-1,3-Bis(2,3,4,5,6-pentafluorophenyl)prop-2-en-1-one
;
_chemical_name_common     Decafluorochalcone
_chemical_formula_moiety     'C15 H2 F10 O'
_chemical_formula_sum     'C15 H2 F10 O'
_chemical_formula_iupac     'C15 H2 F10 O'
_chemical_formula_weight     388.17
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_hall     '-P 2yn'
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     11.4440(10)
_cell_length_b     9.5630(10)
_cell_length_c     12.138(2)
_cell_angle_alpha     90.00
_cell_angle_beta     101.414(3)
_cell_angle_gamma     90.00
_cell_volume     1302.1(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     6932
_cell_measurement_theta_min     2.73
_cell_measurement_theta_max     31.19
_cell_measurement_temperature     93(2)
_exptl_crystal_description     splitter
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.26
_exptl_crystal_size_mid     0.16
_exptl_crystal_size_min     0.14
_exptl_crystal_density_diffrn     1.980
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     760
_exptl_absorpt_coefficient_mu     0.222
_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     93(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     'phi and omega scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     26448
_diffrn_reflns_av_R_equivalents     0.0374
_diffrn_reflns_av_sigmaI/netI     0.0221
_diffrn_reflns_theta_min     2.24
_diffrn_reflns_theta_max     27.50
_diffrn_reflns_theta_full     27.50
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -14
_diffrn_reflns_limit_h_max     14
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     ?
_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     2993
_reflns_number_gt     2404
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0454
_refine_ls_R_factor_gt     0.0316
_refine_ls_wR_factor_gt     0.0748
_refine_ls_wR_factor_ref     0.0795
_refine_ls_goodness_of_fit_ref     1.083
_refine_ls_restrained_S_all     1.083
_refine_ls_number_reflns     2993
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0302P)²+0.8152P] 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     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.334
_refine_diff_density_min     -0.255
_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'
    'F' 'F' 0.0171 0.0103
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 2007)'
_computing_cell_refinement     'SAINT (Bruker, 2007)'
_computing_data_reduction     'SAINT (Bruker, 2007)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (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 -0.08561(10) 0.88461(13) 0.74475(9) 0.0217(3) Uani d . 1 . .
    F F1 0.11079(8) 0.82449(11) 1.13198(7) 0.0219(2) Uani d . 1 . .
    F F2 0.25675(9) 0.81099(10) 1.33222(7) 0.0229(2) Uani d . 1 . .
    F F3 0.47708(9) 0.92977(11) 1.36477(8) 0.0252(2) Uani d . 1 . .
    F F4 0.54620(8) 1.07257(10) 1.19539(8) 0.0235(2) Uani d . 1 . .
    F F5 0.39739(8) 1.09616(10) 0.99452(8) 0.0214(2) Uani d . 1 . .
    F F6 0.21736(9) 0.74714(11) 0.73250(8) 0.0252(2) Uani d . 1 . .
    F F7 0.34571(9) 0.82160(11) 0.57810(8) 0.0264(2) Uani d . 1 . .
    F F8 0.29589(9) 1.06719(11) 0.46224(8) 0.0237(2) Uani d . 1 . .
    F F9 0.10919(9) 1.22599(10) 0.49466(8) 0.0228(2) Uani d . 1 . .
    F F10 -0.02162(8) 1.14862(10) 0.64486(8) 0.0217(2) Uani d . 1 . .
    C C1 0.21650(14) 0.89021(17) 1.14490(13) 0.0170(3) Uani d . 1 . .
    C C2 0.29072(15) 0.88141(17) 1.24884(13) 0.0184(3) Uani d . 1 . .
    C C3 0.40208(15) 0.94296(17) 1.26555(13) 0.0187(3) Uani d . 1 . .
    C C4 0.43704(14) 1.01588(17) 1.17940(13) 0.0182(3) Uani d . 1 . .
    C C5 0.36026(14) 1.02514(17) 1.07695(12) 0.0167(3) Uani d . 1 . .
    C C6 0.24865(14) 0.96066(17) 1.05466(12) 0.0163(3) Uani d . 1 . .
    C C7 0.18133(14) 0.95916(17) 0.93890(13) 0.0170(3) Uani d . 1 . .
    H H7 0.2177 1.0056 0.8852 0.020 Uiso calc R 1 . .
    C C8 0.07515(15) 0.90086(17) 0.89895(13) 0.0189(3) Uani d . 1 . .
    H H8 0.0346 0.8541 0.9493 0.023 Uiso calc R 1 . .
    C C9 0.01954(14) 0.90743(17) 0.77860(13) 0.0168(3) Uani d . 1 . .
    C C10 0.09586(14) 0.94777(17) 0.69495(12) 0.0160(3) Uani d . 1 . .
    C C11 0.18995(15) 0.86724(17) 0.67481(13) 0.0180(3) Uani d . 1 . .
    C C12 0.25647(14) 0.90341(18) 0.59587(13) 0.0193(3) Uani d . 1 . .
    C C13 0.23042(14) 1.02638(18) 0.53571(12) 0.0181(3) Uani d . 1 . .
    C C14 0.13576(14) 1.10771(16) 0.55273(13) 0.0165(3) Uani d . 1 . .
    C C15 0.06936(14) 1.06744(17) 0.63041(13) 0.0167(3) Uani d . 1 . .
_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 C9 . 1.212(2) ?
    F1 C1 . 1.3446(19) ?
    F2 C2 . 1.3358(18) ?
    F3 C3 . 1.3393(17) ?
    F4 C4 . 1.3401(19) ?
    F5 C5 . 1.3458(18) ?
    F6 C11 . 1.3495(19) ?
    F7 C12 . 1.3375(19) ?
    F8 C13 . 1.3317(18) ?
    F9 C14 . 1.3356(18) ?
    F10 C15 . 1.3378(19) ?
    C1 C2 . 1.377(2) ?
    C1 C6 . 1.396(2) ?
    C2 C3 . 1.382(2) ?
    C3 C4 . 1.380(2) ?
    C4 C5 . 1.376(2) ?
    C5 C6 . 1.396(2) ?
    C6 C7 . 1.463(2) ?
    C7 C8 . 1.338(2) ?
    C7 H7 . 0.9500 ?
    C8 C9 . 1.475(2) ?
    C8 H8 . 0.9500 ?
    C9 C10 . 1.514(2) ?
    C10 C11 . 1.384(2) ?
    C10 C15 . 1.386(2) ?
    C11 C12 . 1.381(2) ?
    C12 C13 . 1.385(2) ?
    C13 C14 . 1.382(2) ?
    C14 C15 . 1.378(2) ?
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
    F1 C1 C2 . . 117.12(14) ?
    F1 C1 C6 . . 120.32(14) ?
    C2 C1 C6 . . 122.54(15) ?
    F2 C2 C1 . . 120.38(15) ?
    F2 C2 C3 . . 120.11(14) ?
    C1 C2 C3 . . 119.48(15) ?
    F3 C3 C4 . . 119.90(15) ?
    F3 C3 C2 . . 120.01(14) ?
    C4 C3 C2 . . 120.08(14) ?
    F4 C4 C5 . . 121.00(15) ?
    F4 C4 C3 . . 119.75(14) ?
    C5 C4 C3 . . 119.21(15) ?
    F5 C5 C4 . . 117.72(14) ?
    F5 C5 C6 . . 119.36(13) ?
    C4 C5 C6 . . 122.88(15) ?
    C5 C6 C1 . . 115.74(14) ?
    C5 C6 C7 . . 118.58(14) ?
    C1 C6 C7 . . 125.35(15) ?
    C8 C7 C6 . . 128.34(15) ?
    C8 C7 H7 . . 115.8 ?
    C6 C7 H7 . . 115.8 ?
    C7 C8 C9 . . 121.62(15) ?
    C7 C8 H8 . . 119.2 ?
    C9 C8 H8 . . 119.2 ?
    O1 C9 C8 . . 122.21(15) ?
    O1 C9 C10 . . 118.96(14) ?
    C8 C9 C10 . . 118.81(14) ?
    C11 C10 C15 . . 116.77(15) ?
    C11 C10 C9 . . 123.27(14) ?
    C15 C10 C9 . . 119.90(14) ?
    F6 C11 C12 . . 118.02(14) ?
    F6 C11 C10 . . 119.40(14) ?
    C12 C11 C10 . . 122.56(15) ?
    F7 C12 C11 . . 120.59(15) ?
    F7 C12 C13 . . 120.21(15) ?
    C11 C12 C13 . . 119.20(15) ?
    F8 C13 C14 . . 119.78(15) ?
    F8 C13 C12 . . 120.72(15) ?
    C14 C13 C12 . . 119.50(15) ?
    F9 C14 C15 . . 119.94(14) ?
    F9 C14 C13 . . 120.08(14) ?
    C15 C14 C13 . . 119.98(15) ?
    F10 C15 C14 . . 118.45(14) ?
    F10 C15 C10 . . 119.60(14) ?
    C14 C15 C10 . . 121.93(15) ?
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
    F1 C1 C2 F2 . . . . -0.5(2) ?
    C6 C1 C2 F2 . . . . -178.97(14) ?
    F1 C1 C2 C3 . . . . 177.77(14) ?
    C6 C1 C2 C3 . . . . -0.7(2) ?
    F2 C2 C3 F3 . . . . 1.3(2) ?
    C1 C2 C3 F3 . . . . -177.02(14) ?
    F2 C2 C3 C4 . . . . -179.91(15) ?
    C1 C2 C3 C4 . . . . 1.8(2) ?
    F3 C3 C4 F4 . . . . 0.3(2) ?
    C2 C3 C4 F4 . . . . -178.47(14) ?
    F3 C3 C4 C5 . . . . 178.17(14) ?
    C2 C3 C4 C5 . . . . -0.6(2) ?
    F4 C4 C5 F5 . . . . -1.7(2) ?
    C3 C4 C5 F5 . . . . -179.55(14) ?
    F4 C4 C5 C6 . . . . 176.10(14) ?
    C3 C4 C5 C6 . . . . -1.7(2) ?
    F5 C5 C6 C1 . . . . -179.47(14) ?
    C4 C5 C6 C1 . . . . 2.7(2) ?
    F5 C5 C6 C7 . . . . 6.8(2) ?
    C4 C5 C6 C7 . . . . -171.00(15) ?
    F1 C1 C6 C5 . . . . -179.90(14) ?
    C2 C1 C6 C5 . . . . -1.5(2) ?
    F1 C1 C6 C7 . . . . -6.7(2) ?
    C2 C1 C6 C7 . . . . 171.73(15) ?
    C5 C6 C7 C8 . . . . 178.28(16) ?
    C1 C6 C7 C8 . . . . 5.2(3) ?
    C6 C7 C8 C9 . . . . -179.30(15) ?
    C7 C8 C9 O1 . . . . -162.80(16) ?
    C7 C8 C9 C10 . . . . 15.6(2) ?
    O1 C9 C10 C11 . . . . -116.74(18) ?
    C8 C9 C10 C11 . . . . 64.8(2) ?
    O1 C9 C10 C15 . . . . 60.3(2) ?
    C8 C9 C10 C15 . . . . -118.11(17) ?
    C15 C10 C11 F6 . . . . -177.84(14) ?
    C9 C10 C11 F6 . . . . -0.7(2) ?
    C15 C10 C11 C12 . . . . 0.9(2) ?
    C9 C10 C11 C12 . . . . 178.04(15) ?
    F6 C11 C12 F7 . . . . -0.4(2) ?
    C10 C11 C12 F7 . . . . -179.14(14) ?
    F6 C11 C12 C13 . . . . -179.81(14) ?
    C10 C11 C12 C13 . . . . 1.4(2) ?
    F7 C12 C13 F8 . . . . -2.2(2) ?
    C11 C12 C13 F8 . . . . 177.26(14) ?
    F7 C12 C13 C14 . . . . 178.14(14) ?
    C11 C12 C13 C14 . . . . -2.4(2) ?
    F8 C13 C14 F9 . . . . 0.8(2) ?
    C12 C13 C14 F9 . . . . -179.51(14) ?
    F8 C13 C14 C15 . . . . -178.60(13) ?
    C12 C13 C14 C15 . . . . 1.1(2) ?
    F9 C14 C15 F10 . . . . 0.5(2) ?
    C13 C14 C15 F10 . . . . 179.96(13) ?
    F9 C14 C15 C10 . . . . -178.06(13) ?
    C13 C14 C15 C10 . . . . 1.4(2) ?
    C11 C10 C15 F10 . . . . 179.11(13) ?
    C9 C10 C15 F10 . . . . 1.9(2) ?
    C11 C10 C15 C14 . . . . -2.3(2) ?
    C9 C10 C15 C14 . . . . -179.54(14) ?
data_global
_journal_date_recd_electronic     2010-06-21
_journal_date_accepted     2010-06-30
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      8
_journal_page_first     o1931
_journal_page_last     o1931
_journal_paper_category     QO
_journal_coeditor_code     IM2215
_publ_contact_author_name     'Prof. Dr. Edwin Weber'
_publ_contact_author_address
;Institut für Organische Chemie
TU Bergakademie Freiberg
Leipziger Straße 29
D-09596 Freiberg/Sachsen
Germany
;
_publ_contact_author_email     Edwin.Weber@chemie.tu-freiberg.de
_publ_contact_author_fax     '+49 (0) 3731/393170'
_publ_contact_author_phone     '+49 (0) 3731/392386'
_publ_section_title
;
(E)-1,3-Bis(2,3,4,5,6-pentafluorophenyl)prop-2-en-1-one
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Schwarzer, Anke' .
;
Institut für Organische Chemie
TU Bergakademie Freiberg
Leipziger Strasse 29
D-09596 Freiberg/Sachsen
Germany
;
    'Weber, Edwin' .
;
Institut für Organische Chemie
TU Bergakademie Freiberg
Leipziger Strasse 29
D-09596 Freiberg/Sachsen
Germany
;
