##############################################################################
###                                                                        ###
###        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_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
{[(5-fluoro-2-trifluoromenthylphenyl)
iminomethyl]phenolato-K²N,O}copper(II)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C28 H16 Cu F8 N2 O2'
_chemical_formula_sum     'C28 H16 Cu F8 N2 O2'
_chemical_formula_iupac     ' [Cu (C14 H8 F4 N O )2]'
_chemical_formula_weight     627.97
_chemical_melting_point     ?
_symmetry_cell_setting     'Monoclinic'
_symmetry_space_group_name_H-M     'P2(1)/c'
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     12.805(3)
_cell_length_b     7.0850(14)
_cell_length_c     13.893(3)
_cell_angle_alpha     90.00
_cell_angle_beta     96.481(3)
_cell_angle_gamma     90.00
_cell_volume     1252.3(4)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     2401
_cell_measurement_theta_min     2.10
_cell_measurement_theta_max     26.00
_cell_measurement_temperature     296(2)
_exptl_crystal_description     block
_exptl_crystal_colour     blue
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.15
_exptl_crystal_size_min     0.15
_exptl_crystal_density_diffrn     1.665
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     630
_exptl_absorpt_coefficient_mu     0.963
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.8308
_exptl_absorpt_correction_T_max     0.8691
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     296(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 APEX-II area-detector diffractometer'
_diffrn_measurement_method     'φ and ω scan'
_diffrn_reflns_number     7797
_diffrn_reflns_av_R_equivalents     0.0404
_diffrn_reflns_av_sigmaI/netI     0.0629
_diffrn_reflns_theta_min     2.95
_diffrn_reflns_theta_max     26.00
_diffrn_reflns_theta_full     26.00
_diffrn_measured_fraction_theta_max     0.977
_diffrn_measured_fraction_theta_full     0.977
_diffrn_reflns_limit_h_min     -15
_diffrn_reflns_limit_h_max     15
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     17
_diffrn_standards_number     ?
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_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     2401
_reflns_number_gt     1405
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0579
_refine_ls_R_factor_gt     0.0349
_refine_ls_wR_factor_gt     0.0849
_refine_ls_wR_factor_ref     0.0885
_refine_ls_goodness_of_fit_ref     0.848
_refine_ls_restrained_S_all     0.905
_refine_ls_number_reflns     2401
_refine_ls_number_parameters     187
_refine_ls_number_restraints     36
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.0471P)²] 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     0.530
_refine_diff_density_min     -0.281
_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'
    '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'
    'Cu' 'Cu' 0.3201 1.2651
                         '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'
_computing_data_collection     'SMART (Bruker,1998)'
_computing_cell_refinement     SMART
_computing_data_reduction     'SAINT (Bruker, 1999)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Bruker, 1998)'
_computing_publication_material     SHELXTL
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
    C C1 0.3555(2) 0.1122(4) 0.3382(2) 0.0487(8) Uani d . 1 . .
    C C2 0.2540(3) 0.0977(5) 0.2878(2) 0.0609(9) Uani d . 1 . .
    H H2 0.1993 0.0516 0.3198 0.073 Uiso calc R 1 . .
    C C3 0.2342(3) 0.1501(5) 0.1926(2) 0.0651(9) Uani d . 1 . .
    H H3 0.1662 0.1396 0.1614 0.078 Uiso calc R 1 . .
    C C4 0.3137(3) 0.2189(5) 0.1416(2) 0.0625(9) Uani d . 1 . .
    H H4 0.3000 0.2509 0.0765 0.075 Uiso calc R 1 . .
    C C5 0.4121(3) 0.2383(4) 0.1894(2) 0.0593(9) Uani d . 1 . .
    H H5 0.4654 0.2856 0.1559 0.071 Uiso calc R 1 . .
    C C6 0.4358(2) 0.1889(4) 0.2877(2) 0.0461(7) Uani d . 1 . .
    C C7 0.5386(2) 0.2258(4) 0.3337(2) 0.0507(8) Uani d . 1 . .
    H H7 0.5836 0.2915 0.2977 0.061 Uiso calc R 1 . .
    C C8 0.6815(2) 0.2335(4) 0.4528(2) 0.0494(8) Uani d . 1 . .
    C C9 0.7651(2) 0.1847(4) 0.4033(2) 0.0538(8) Uani d . 1 . .
    H H9 0.7532 0.1176 0.3456 0.065 Uiso calc R 1 . .
    C C10 0.8664(2) 0.2347(5) 0.4391(2) 0.0582(9) Uani d . 1 . .
    C C11 0.9537(3) 0.1821(7) 0.3826(3) 0.0793(11) Uani d U 1 . .
    C C12 0.8842(3) 0.3345(5) 0.5238(3) 0.0704(10) Uani d . 1 . .
    H H12 0.9526 0.3665 0.5480 0.084 Uiso calc R 1 . .
    C C13 0.8018(3) 0.3879(6) 0.5735(3) 0.0778(11) Uani d . 1 . .
    H H13 0.8135 0.4587 0.6301 0.093 Uiso calc R 1 . .
    C C14 0.7025(3) 0.3341(5) 0.5376(2) 0.0624(9) Uani d . 1 . .
    Cu Cu1 0.5000 0.0000 0.5000 0.0479(2) Uani d S 1 . .
    F F1 0.9467(2) 0.0170(4) 0.3449(3) 0.1432(12) Uani d U 1 . .
    F F2 0.9681(2) 0.3038(4) 0.3156(2) 0.1531(13) Uani d U 1 . .
    F F3 1.04688(18) 0.1823(4) 0.4370(2) 0.1327(10) Uani d U 1 . .
    F F4 0.62151(16) 0.3845(3) 0.58617(14) 0.0905(7) Uani d . 1 . .
    N N1 0.57589(19) 0.1775(3) 0.42057(17) 0.0489(6) Uani d . 1 . .
    O O1 0.37125(15) 0.0560(3) 0.42816(14) 0.0600(6) 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
    C1 0.0504(19) 0.0443(19) 0.054(2) 0.0004(15) 0.0161(16) -0.0011(16)
    C2 0.054(2) 0.066(2) 0.065(2) -0.0039(17) 0.0156(18) 0.0040(19)
    C3 0.061(2) 0.062(2) 0.071(2) -0.0002(17) 0.0022(19) 0.004(2)
    C4 0.078(3) 0.056(2) 0.054(2) 0.0024(18) 0.009(2) 0.0089(17)
    C5 0.071(2) 0.053(2) 0.057(2) 0.0026(17) 0.0200(18) 0.0106(17)
    C6 0.0513(19) 0.0424(18) 0.0474(18) -0.0021(14) 0.0173(15) -0.0004(15)
    C7 0.056(2) 0.0429(19) 0.057(2) -0.0035(15) 0.0229(17) 0.0041(16)
    C8 0.0499(19) 0.0465(19) 0.0546(19) -0.0107(15) 0.0173(16) 0.0013(16)
    C9 0.056(2) 0.054(2) 0.0537(19) -0.0089(16) 0.0170(16) 0.0017(16)
    C10 0.052(2) 0.056(2) 0.068(2) -0.0073(16) 0.0149(18) 0.0133(18)
    C11 0.050(2) 0.093(3) 0.099(3) -0.002(2) 0.024(2) 0.011(3)
    C12 0.057(2) 0.080(3) 0.074(2) -0.0210(19) 0.0068(19) 0.004(2)
    C13 0.081(3) 0.087(3) 0.068(2) -0.029(2) 0.019(2) -0.018(2)
    C14 0.061(2) 0.069(2) 0.062(2) -0.0190(18) 0.0243(19) -0.0085(19)
    Cu1 0.0499(3) 0.0530(4) 0.0441(3) -0.0081(3) 0.0199(2) 0.0002(3)
    F1 0.1019(19) 0.128(2) 0.215(3) -0.0180(17) 0.082(2) -0.071(2)
    F2 0.140(2) 0.179(3) 0.161(2) 0.056(2) 0.108(2) 0.083(2)
    F3 0.0627(15) 0.186(3) 0.153(2) 0.0084(16) 0.0282(16) -0.008(2)
    F4 0.0820(14) 0.1087(17) 0.0889(14) -0.0275(13) 0.0449(12) -0.0393(13)
    N1 0.0511(15) 0.0495(16) 0.0487(15) -0.0074(12) 0.0175(13) -0.0009(13)
    O1 0.0519(13) 0.0823(17) 0.0485(12) -0.0086(11) 0.0177(10) 0.0140(11)
_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
    C1 O1 . 1.305(3) ?
    C1 C2 . 1.410(4) ?
    C1 C6 . 1.417(4) ?
    C2 C3 . 1.369(4) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.393(4) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.363(4) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.409(4) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.421(4) ?
    C7 N1 . 1.293(3) ?
    C7 H7 . 0.9300 ?
    C8 C14 . 1.377(4) ?
    C8 C9 . 1.380(4) ?
    C8 N1 . 1.431(3) ?
    C9 C10 . 1.381(4) ?
    C9 H9 . 0.9300 ?
    C10 C12 . 1.370(4) ?
    C10 C11 . 1.485(5) ?
    C11 F1 . 1.280(4) ?
    C11 F2 . 1.297(4) ?
    C11 F3 . 1.338(4) ?
    C12 C13 . 1.378(5) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.367(4) ?
    C13 H13 . 0.9300 ?
    C14 F4 . 1.348(3) ?
    Cu1 O1 3_656 1.871(2) ?
    Cu1 O1 . 1.871(2) y
    Cu1 N1 . 1.996(2) y
    Cu1 N1 3_656 1.996(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
    O1 C1 C2 . . 119.2(3) ?
    O1 C1 C6 . . 123.3(3) ?
    C2 C1 C6 . . 117.5(3) ?
    C3 C2 C1 . . 121.3(3) ?
    C3 C2 H2 . . 119.3 ?
    C1 C2 H2 . . 119.3 ?
    C2 C3 C4 . . 121.3(3) ?
    C2 C3 H3 . . 119.3 ?
    C4 C3 H3 . . 119.3 ?
    C5 C4 C3 . . 118.5(3) ?
    C5 C4 H4 . . 120.8 ?
    C3 C4 H4 . . 120.8 ?
    C4 C5 C6 . . 122.2(3) ?
    C4 C5 H5 . . 118.9 ?
    C6 C5 H5 . . 118.9 ?
    C5 C6 C1 . . 119.1(3) ?
    C5 C6 C7 . . 118.5(3) ?
    C1 C6 C7 . . 122.3(3) ?
    N1 C7 C6 . . 126.7(3) ?
    N1 C7 H7 . . 116.7 ?
    C6 C7 H7 . . 116.7 ?
    C14 C8 C9 . . 117.9(3) ?
    C14 C8 N1 . . 119.8(3) ?
    C9 C8 N1 . . 122.2(3) ?
    C8 C9 C10 . . 120.4(3) ?
    C8 C9 H9 . . 119.8 ?
    C10 C9 H9 . . 119.8 ?
    C12 C10 C9 . . 120.0(3) ?
    C12 C10 C11 . . 121.4(3) ?
    C9 C10 C11 . . 118.6(3) ?
    F1 C11 F2 . . 108.9(4) ?
    F1 C11 F3 . . 104.4(4) ?
    F2 C11 F3 . . 102.4(3) ?
    F1 C11 C10 . . 115.0(3) ?
    F2 C11 C10 . . 112.9(3) ?
    F3 C11 C10 . . 112.2(4) ?
    C10 C12 C13 . . 120.6(3) ?
    C10 C12 H12 . . 119.7 ?
    C13 C12 H12 . . 119.7 ?
    C14 C13 C12 . . 118.3(3) ?
    C14 C13 H13 . . 120.9 ?
    C12 C13 H13 . . 120.9 ?
    F4 C14 C13 . . 118.7(3) ?
    F4 C14 C8 . . 118.6(3) ?
    C13 C14 C8 . . 122.7(3) ?
    O1 Cu1 O1 3_656 . 180.0 y
    O1 Cu1 N1 3_656 . 88.50(9) y
    O1 Cu1 N1 . . 91.50(9) y
    O1 Cu1 N1 3_656 3_656 91.50(9) ?
    O1 Cu1 N1 . 3_656 88.50(9) ?
    N1 Cu1 N1 . 3_656 180.00(11) y
    C7 N1 C8 . . 117.1(2) ?
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
    O1 C1 C2 C3 . . . . -178.2(3) ?
    C6 C1 C2 C3 . . . . 2.0(5) ?
    C1 C2 C3 C4 . . . . 0.4(5) ?
    C2 C3 C4 C5 . . . . -1.8(5) ?
    C3 C4 C5 C6 . . . . 0.8(5) ?
    C4 C5 C6 C1 . . . . 1.6(5) ?
    C4 C5 C6 C7 . . . . -175.7(3) ?
    O1 C1 C6 C5 . . . . 177.3(3) ?
    C2 C1 C6 C5 . . . . -2.9(4) ?
    O1 C1 C6 C7 . . . . -5.5(5) ?
    C2 C1 C6 C7 . . . . 174.2(3) ?
    C5 C6 C7 N1 . . . . -174.5(3) ?
    C1 C6 C7 N1 . . . . 8.3(5) ?
    C14 C8 C9 C10 . . . . 0.5(5) ?
    N1 C8 C9 C10 . . . . -177.2(3) ?
    C8 C9 C10 C12 . . . . -0.4(5) ?
    C8 C9 C10 C11 . . . . -178.9(3) ?
    C12 C10 C11 F1 . . . . 140.8(4) ?
    C9 C10 C11 F1 . . . . -40.7(5) ?
    C12 C10 C11 F2 . . . . -93.5(5) ?
    C9 C10 C11 F2 . . . . 85.0(5) ?
    C12 C10 C11 F3 . . . . 21.6(5) ?
    C9 C10 C11 F3 . . . . -159.9(3) ?
    C9 C10 C12 C13 . . . . -0.8(5) ?
    C11 C10 C12 C13 . . . . 177.7(3) ?
    C10 C12 C13 C14 . . . . 1.8(6) ?
    C12 C13 C14 F4 . . . . 179.5(3) ?
    C12 C13 C14 C8 . . . . -1.8(6) ?
    C9 C8 C14 F4 . . . . 179.3(3) ?
    N1 C8 C14 F4 . . . . -2.9(5) ?
    C9 C8 C14 C13 . . . . 0.6(5) ?
    N1 C8 C14 C13 . . . . 178.4(3) ?
    C6 C7 N1 C8 . . . . -178.7(3) ?
    C6 C7 N1 Cu1 . . . . 10.5(4) ?
    C14 C8 N1 C7 . . . . 125.7(3) ?
    C9 C8 N1 C7 . . . . -56.6(4) ?
    C14 C8 N1 Cu1 . . . . -63.2(4) ?
    C9 C8 N1 Cu1 . . . . 114.4(3) ?
    O1 Cu1 N1 C7 3_656 . . . 156.8(2) ?
    O1 Cu1 N1 C7 . . . . -23.2(2) ?
    O1 Cu1 N1 C8 3_656 . . . -13.7(2) ?
    O1 Cu1 N1 C8 . . . . 166.3(2) ?
    C2 C1 O1 Cu1 . . . . 162.5(2) ?
    C6 C1 O1 Cu1 . . . . -17.8(4) ?
    N1 Cu1 O1 C1 . . . . 27.4(3) ?
    N1 Cu1 O1 C1 3_656 . . . -152.6(3) ?
data_a
_journal_date_recd_electronic     2006-12-31
_journal_date_accepted     2007-01-02
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      2
_journal_page_first     m390
_journal_page_last     m391
_journal_paper_category     EM
_journal_coeditor_code     NG2198
_publ_contact_author_name     'Ming-Hua,Yang'
_publ_contact_author_address
;
Department of chemistry,
Lishui College,
323000 Lishui, ZheJiang
P.R. China
;
_publ_contact_author_email     zjlsxyhx@126.com
_publ_contact_author_fax     '86 571-88303459'
_publ_contact_author_phone     '86 571-88303459'
_publ_section_title
;
Bis{[(5-fluoro-2-trifluoromenthylphenyl)
iminomethyl]phenolato-κ²N,O}copper(II)
;
loop_
    _publ_author_name
    _publ_author_address
    'Wang, Liang-Gui'
;
Department of Chemistry, Lishui College,
323000 Lishui, ZheJiang
People's Republic of China
;
    'Zheng, Yun-Fa'
;
Department of Chemistry, Lishui College,
323000 Lishui, ZheJiang
People's Republic of China
;
