##############################################################################
###                                                                        ###
###        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.                                        #
#                                                                            #
# 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           #
# scientific community so long as proper attribution is given to the journal # 
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data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
N-{[2,5-Dichloro-4-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]aminocarbonyl}-
2,6-difluorobenzamide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C17 H8 Cl2 F8 N2 O3'
_chemical_formula_sum     'C17 H8 Cl2 F8 N2 O3'
_chemical_formula_iupac     'C17 H8 Cl2 F8 N2 O3'
_chemical_formula_weight     511.15
_chemical_melting_point     ?
_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     9.2300(18)
_cell_length_b     16.404(3)
_cell_length_c     14.074(3)
_cell_angle_alpha     90.00
_cell_angle_beta     108.77(3)
_cell_angle_gamma     90.00
_cell_volume     2017.6(8)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     9
_cell_measurement_theta_max     12
_cell_measurement_temperature     294(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.40
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.683
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1016
_exptl_absorpt_coefficient_mu     0.417
_exptl_absorpt_correction_type     psi-scan
_exptl_absorpt_process_details     '(North et al.,  1968)'
_exptl_absorpt_correction_T_min     0.8508
_exptl_absorpt_correction_T_max     0.9212
_exptl_special_details
;
;
_diffrn_ambient_temperature     294(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     'Enraf--Nonius CAD-4'
_diffrn_measurement_method     'ω/2θ'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     3609
_diffrn_reflns_av_R_equivalents     0.0000
_diffrn_reflns_av_sigmaI/netI     0.0651
_diffrn_reflns_theta_min     1.97
_diffrn_reflns_theta_max     25.17
_diffrn_reflns_theta_full     25.17
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     0
_diffrn_reflns_limit_k_max     19
_diffrn_reflns_limit_l_min     0
_diffrn_reflns_limit_l_max     16
_diffrn_standards_number     3
_diffrn_standards_interval_count     200
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
_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     3609
_reflns_number_gt     1922
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1520
_refine_ls_R_factor_gt     0.0856
_refine_ls_wR_factor_gt     0.2068
_refine_ls_wR_factor_ref     0.2475
_refine_ls_goodness_of_fit_ref     1.086
_refine_ls_restrained_S_all     1.084
_refine_ls_number_reflns     3609
_refine_ls_number_parameters     283
_refine_ls_number_restraints     96
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.1258P)²+1.1819P] 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     0.424
_refine_diff_density_min     -0.345
_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'
    'N' 'N' 0.0061 0.0033
                         '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'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_cell_refinement     'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction     'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 for Windows (Farrugia, 1997)'
_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
    Cl Cl1 1.21022(15) 1.15534(9) 0.61828(12) 0.0527(5) Uani d . 1 . .
    Cl Cl2 1.06547(19) 0.83402(11) 0.80001(17) 0.0914(8) Uani d . 1 . .
    F F1 0.4001(5) 0.7889(3) 0.7184(3) 0.0975(16) Uani d . 1 . .
    F F2 0.4224(4) 0.8023(3) 0.3906(3) 0.0810(13) Uani d . 1 . .
    F F3 1.5260(5) 1.0359(3) 0.6887(5) 0.1116(18) Uani d . 1 . .
    F F4 1.5722(4) 0.9618(3) 0.8001(4) 0.1039(17) Uani d . 1 . .
    F F5 1.8146(6) 1.0579(3) 0.7942(5) 0.145(3) Uani d . 1 . .
    F F6 1.8127(6) 1.0156(3) 0.9703(4) 0.1121(18) Uani d . 1 . .
    F F7 1.9281(6) 1.1152(3) 0.9350(4) 0.119(2) Uani d . 1 . .
    F F8 1.6616(6) 1.1347(3) 0.9601(4) 0.1029(15) Uani d . 1 . .
    O O1 0.6850(4) 0.7921(2) 0.6546(4) 0.0703(15) Uani d . 1 . .
    O O2 0.6981(4) 1.0216(3) 0.5376(3) 0.0505(11) Uani d . 1 . .
    O O3 1.4248(4) 1.0694(3) 0.7916(4) 0.0758(16) Uani d . 1 . .
    N N1 0.5870(4) 0.9045(2) 0.5577(3) 0.0359(11) Uani d . 1 . .
    H H1A 0.5033 0.9242 0.5175 0.043 Uiso calc R 1 . .
    N N2 0.8483(4) 0.9219(2) 0.6377(3) 0.0327(10) Uani d . 1 . .
    H H2A 0.8468 0.8724 0.6576 0.039 Uiso calc R 1 . .
    C C1 0.1954(8) 0.7296(5) 0.5816(6) 0.074(2) Uani d U 1 . .
    H H1B 0.1414 0.7140 0.6242 0.089 Uiso calc R 1 . .
    C C2 0.1405(7) 0.7183(4) 0.4832(5) 0.0588(17) Uani d U 1 . .
    H H2B 0.0444 0.6945 0.4569 0.071 Uiso calc R 1 . .
    C C3 0.2142(7) 0.7389(4) 0.4199(5) 0.0607(17) Uani d U 1 . .
    H H3A 0.1704 0.7275 0.3519 0.073 Uiso calc R 1 . .
    C C4 0.3505(6) 0.7758(4) 0.4526(4) 0.0450(14) Uani d U 1 . .
    C C5 0.4228(6) 0.7893(3) 0.5551(4) 0.0435(14) Uani d U 1 . .
    C C6 0.3397(7) 0.7666(4) 0.6175(5) 0.0568(16) Uani d U 1 . .
    C C7 0.5790(6) 0.8247(3) 0.5960(4) 0.0437(14) Uani d . 1 . .
    C C8 0.7151(6) 0.9534(3) 0.5785(4) 0.0407(14) Uani d . 1 . .
    C C9 0.9852(5) 0.9614(3) 0.6689(4) 0.0330(12) Uani d U 1 . .
    C C10 1.0214(5) 1.0332(3) 0.6291(4) 0.0368(12) Uani d U 1 . .
    H H10A 0.9477 1.0595 0.5770 0.044 Uiso calc R 1 . .
    C C11 1.1661(5) 1.0655(3) 0.6667(4) 0.0355(12) Uani d U 1 . .
    C C12 1.2807(6) 1.0310(4) 0.7494(5) 0.0518(16) Uani d U 1 . .
    C C13 1.2445(7) 0.9591(4) 0.7901(5) 0.0572(17) Uani d U 1 . .
    H H13A 1.3159 0.9350 0.8453 0.069 Uiso calc R 1 . .
    C C14 1.1065(5) 0.9252(3) 0.7492(4) 0.0391(13) Uani d U 1 . .
    C C15 1.5460(7) 1.0386(4) 0.8024(7) 0.079(3) Uani d . 1 . .
    C C16 1.6854(8) 1.0845(5) 0.8271(9) 0.107(4) Uani d . 1 . .
    H H16A 1.6576 1.1394 0.7999 0.129 Uiso calc R 1 . .
    C C17 1.7772(11) 1.0946(6) 0.9319(7) 0.089 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
    Cl1 0.0401(8) 0.0436(9) 0.0782(11) -0.0152(6) 0.0242(7) -0.0007(7)
    Cl2 0.0513(10) 0.0599(12) 0.1330(18) -0.0100(8) -0.0123(10) 0.0497(12)
    F1 0.097(3) 0.135(4) 0.051(3) -0.054(3) 0.010(2) 0.026(2)
    F2 0.086(3) 0.103(3) 0.059(3) -0.045(3) 0.030(2) -0.034(2)
    F3 0.099(4) 0.106(4) 0.133(5) -0.034(3) 0.041(3) -0.032(3)
    F4 0.054(2) 0.072(3) 0.172(5) -0.010(2) 0.019(3) -0.015(3)
    F5 0.092(3) 0.141(5) 0.225(7) -0.023(3) 0.082(4) -0.111(5)
    F6 0.127(4) 0.104(4) 0.095(4) -0.017(3) 0.021(3) 0.052(3)
    F7 0.099(3) 0.083(3) 0.116(4) -0.024(3) -0.048(3) 0.006(3)
    F8 0.097(3) 0.111(4) 0.103(4) -0.001(3) 0.034(3) -0.012(3)
    O1 0.029(2) 0.047(3) 0.107(4) 0.0006(18) -0.017(2) 0.037(2)
    O2 0.046(2) 0.047(3) 0.057(3) -0.0033(19) 0.013(2) -0.005(2)
    O3 0.035(2) 0.043(3) 0.129(5) -0.009(2) -0.001(2) 0.009(3)
    N1 0.028(2) 0.019(2) 0.058(3) 0.0007(17) 0.009(2) 0.0093(19)
    N2 0.028(2) 0.025(2) 0.043(3) -0.0005(17) 0.0085(19) -0.0044(19)
    C1 0.070(4) 0.082(5) 0.076(4) -0.028(4) 0.032(4) 0.017(4)
    C2 0.046(3) 0.051(4) 0.071(4) -0.016(3) 0.007(3) 0.003(3)
    C3 0.059(4) 0.061(4) 0.051(4) -0.023(3) 0.002(3) -0.014(3)
    C4 0.045(3) 0.046(3) 0.042(3) -0.003(3) 0.011(3) -0.004(3)
    C5 0.039(3) 0.042(3) 0.047(3) -0.006(2) 0.011(2) 0.010(3)
    C6 0.044(3) 0.067(4) 0.053(4) -0.009(3) 0.007(3) 0.014(3)
    C7 0.045(3) 0.039(3) 0.047(4) -0.010(3) 0.016(3) 0.004(3)
    C8 0.037(3) 0.027(3) 0.051(4) 0.000(2) 0.005(3) 0.009(3)
    C9 0.026(2) 0.036(3) 0.036(3) 0.000(2) 0.009(2) -0.005(2)
    C10 0.032(2) 0.040(3) 0.042(3) -0.007(2) 0.016(2) -0.003(2)
    C11 0.033(3) 0.035(3) 0.044(3) -0.009(2) 0.020(2) 0.008(2)
    C12 0.030(3) 0.053(4) 0.065(4) -0.003(2) 0.006(3) 0.004(3)
    C13 0.042(3) 0.051(4) 0.071(4) 0.013(3) 0.007(3) 0.017(3)
    C14 0.022(2) 0.042(3) 0.049(3) 0.012(2) 0.005(2) 0.009(2)
    C15 0.029(3) 0.050(5) 0.142(8) 0.006(3) 0.007(4) -0.014(4)
    C16 0.041(4) 0.046(4) 0.219(11) -0.009(3) 0.021(5) 0.007(6)
    C17 0.080 0.089 0.096 -0.006 0.026 0.004
_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
    Cl1 C11 . 1.727(5) ?
    Cl2 C14 . 1.751(6) ?
    F1 C6 . 1.398(7) ?
    F2 C4 . 1.327(7) ?
    F3 C15 . 1.552(10) ?
    F4 C15 . 1.284(8) ?
    F5 C16 . 1.477(9) ?
    F6 C17 . 1.403(10) ?
    F7 C17 . 1.420(10) ?
    F8 C17 . 1.415(10) ?
    O1 C7 . 1.186(6) ?
    N1 C8 . 1.380(6) ?
    N1 C7 . 1.427(7) ?
    N1 H1A . 0.8600 ?
    C1 C2 . 1.327(10) ?
    C1 C6 . 1.401(9) ?
    C1 H1B . 0.9300 ?
    N2 C8 . 1.347(6) ?
    N2 C9 . 1.361(6) ?
    N2 H2A . 0.8600 ?
    O2 C8 . 1.245(6) ?
    C2 C3 . 1.326(9) ?
    C2 H2B . 0.9300 ?
    O3 C15 . 1.191(7) ?
    O3 C12 . 1.418(6) ?
    C3 C4 . 1.338(8) ?
    C3 H3A . 0.9300 ?
    C4 C5 . 1.399(8) ?
    C5 C6 . 1.389(8) ?
    C5 C7 . 1.488(7) ?
    C9 C10 . 1.390(7) ?
    C9 C14 . 1.439(7) ?
    C10 C11 . 1.374(7) ?
    C10 H10A . 0.9300 ?
    C11 C12 . 1.414(7) ?
    C12 C13 . 1.398(8) ?
    C13 C14 . 1.338(8) ?
    C13 H13A . 0.9300 ?
    C15 C16 . 1.434(9) ?
    C16 C17 . 1.455(13) ?
    C16 H16A . 0.9800 ?
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
    C8 N1 C7 . . 126.7(4) ?
    C8 N1 H1A . . 116.6 ?
    C7 N1 H1A . . 116.6 ?
    C2 C1 C6 . . 115.8(6) ?
    C2 C1 H1B . . 122.1 ?
    C6 C1 H1B . . 122.1 ?
    C8 N2 C9 . . 125.8(4) ?
    C8 N2 H2A . . 117.1 ?
    C9 N2 H2A . . 117.1 ?
    C1 C2 C3 . . 124.0(6) ?
    C1 C2 H2B . . 118.0 ?
    C3 C2 H2B . . 118.0 ?
    C15 O3 C12 . . 125.5(6) ?
    C2 C3 C4 . . 120.9(6) ?
    C2 C3 H3A . . 119.6 ?
    C4 C3 H3A . . 119.6 ?
    F2 C4 C3 . . 122.4(6) ?
    F2 C4 C5 . . 117.0(5) ?
    C3 C4 C5 . . 120.7(6) ?
    C6 C5 C4 . . 115.6(5) ?
    C6 C5 C7 . . 121.6(5) ?
    C4 C5 C7 . . 122.8(5) ?
    C5 C6 F1 . . 116.8(5) ?
    C5 C6 C1 . . 122.9(6) ?
    F1 C6 C1 . . 120.1(6) ?
    O1 C7 N1 . . 123.1(5) ?
    O1 C7 C5 . . 125.0(5) ?
    N1 C7 C5 . . 111.9(5) ?
    O2 C8 N2 . . 125.8(5) ?
    O2 C8 N1 . . 116.9(4) ?
    N2 C8 N1 . . 117.2(5) ?
    N2 C9 C10 . . 126.3(5) ?
    N2 C9 C14 . . 117.6(5) ?
    C10 C9 C14 . . 116.0(4) ?
    C11 C10 C9 . . 120.1(5) ?
    C11 C10 H10A . . 120.0 ?
    C9 C10 H10A . . 120.0 ?
    C10 C11 C12 . . 122.7(5) ?
    C10 C11 Cl1 . . 120.0(4) ?
    C12 C11 Cl1 . . 117.2(4) ?
    C13 C12 C11 . . 117.4(5) ?
    C13 C12 O3 . . 121.2(5) ?
    C11 C12 O3 . . 121.4(5) ?
    C14 C13 C12 . . 119.7(5) ?
    C14 C13 H13A . . 120.2 ?
    C12 C13 H13A . . 120.2 ?
    C13 C14 C9 . . 123.9(5) ?
    C13 C14 Cl2 . . 118.8(4) ?
    C9 C14 Cl2 . . 117.2(4) ?
    O3 C15 F4 . . 126.1(6) ?
    O3 C15 C16 . . 122.7(7) ?
    F4 C15 C16 . . 111.1(6) ?
    O3 C15 F3 . . 94.9(6) ?
    F4 C15 F3 . . 84.7(6) ?
    C16 C15 F3 . . 93.7(7) ?
    C15 C16 C17 . . 119.4(9) ?
    C15 C16 F5 . . 121.4(7) ?
    C17 C16 F5 . . 94.9(6) ?
    C15 C16 H16A . . 106.6 ?
    C17 C16 H16A . . 106.6 ?
    F5 C16 H16A . . 106.6 ?
    F6 C17 F8 . . 115.2(7) ?
    F6 C17 F7 . . 95.9(6) ?
    F8 C17 F7 . . 134.6(8) ?
    F6 C17 C16 . . 105.8(7) ?
    F8 C17 C16 . . 95.3(7) ?
    F7 C17 C16 . . 107.7(7) ?
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
    N2 H2A Cl2 . 0.86 2.43 2.892(4) 114.7 yes
    N2 H2A O1 . 0.86 1.98 2.664(6) 135.4 yes
    N1 H1A O2 3_676 0.86 1.98 2.814(6) 163.2 yes
    C10 H10A O2 . 0.93 2.28 2.851(6) 119.0 yes
data_global
_journal_date_recd_electronic     2008-08-06
_journal_date_accepted     2008-08-08
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      9
_journal_page_first     o1756
_journal_page_last     o1756
_journal_paper_category     QO
_journal_coeditor_code     HK2510
_publ_contact_author_name     'Professor Fang-shi Li'
_publ_contact_author_address
;
'Fang-shi Li'
Department of Applied Chemistry
College of Science
Nanjing University of Technology
Xinmofan Road No.5
Nanjing 210009
People's Republic of China
;
_publ_contact_author_email     fangshi.li@njut.edu.cn
_publ_contact_author_fax     '86 25  83587450'
_publ_contact_author_phone     '86 25 83587450'
_publ_section_title
;\
N-{[2,5-Dichloro-4-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]aminocarbonyl}-\
2,6-difluorobenzamide
;
loop_
    _publ_author_name
    _publ_author_address
    'Yin-hong Liu'
;
Department of Applied Chemistry,
College of Science,
Nanjing University of Technology,
Xinmofan Road No. 5
Nanjing 210009
People's Republic of China
;
    'Fang-shi Li'
;
Department of Applied Chemistry,
College of Science,
Nanjing University of Technology,
Xinmofan Road No. 5
Nanjing 210009
People's Republic of China
;
    'Yi Li'
;
Department of Applied Chemistry,
College of Science,
Nanjing University of Technology,
Xinmofan Road No. 5
Nanjing 210009
People's Republic of China
;
