# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_101208a1
#TrackingRef 'web_deposit_cif_file_0_AkikoHori_1344479020.101208a1.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C44 H18 Cu F20 O6'
_chemical_formula_sum            'C44 H18 Cu F20 O6'
_chemical_formula_weight         1086.13

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.7020(19)
_cell_length_b                   11.163(3)
_cell_length_c                   11.884(3)
_cell_angle_alpha                106.861(2)
_cell_angle_beta                 92.790(2)
_cell_angle_gamma                94.258(2)
_cell_volume                     972.5(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    100
_cell_measurement_reflns_used    6538
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      27.83

_exptl_crystal_description       prismatic
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.855
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             539
_exptl_absorpt_coefficient_mu    0.712
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8421
_exptl_absorpt_correction_T_max  0.9007
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            10973
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_av_sigmaI/netI    0.0204
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.66
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4340
_reflns_number_gt                3996
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0345P)²+0.5996P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4340
_refine_ls_number_parameters     323
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0271
_refine_ls_wR_factor_ref         0.0729
_refine_ls_wR_factor_gt          0.0710
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.5000 0.5000 0.0000 0.01318(8) Uani 1 2 d S . .
O1 O 0.29896(14) 0.39264(10) -0.08305(9) 0.0150(2) Uani 1 1 d . . .
O2 O 0.44627(14) 0.47482(10) 0.15018(9) 0.0156(2) Uani 1 1 d . . .
O3 O 0.33892(15) 0.70094(11) 0.05480(10) 0.0211(2) Uani 1 1 d . . .
C1 C 0.01195(19) 0.24255(14) -0.23100(13) 0.0146(3) Uani 1 1 d . . .
C2 C -0.0695(2) 0.15055(15) -0.32726(13) 0.0170(3) Uani 1 1 d . . .
C3 C -0.0662(2) 0.02533(15) -0.33256(14) 0.0184(3) Uani 1 1 d . . .
C4 C 0.0152(2) -0.00685(14) -0.24086(14) 0.0185(3) Uani 1 1 d . . .
C5 C 0.0962(2) 0.08641(14) -0.14560(13) 0.0160(3) Uani 1 1 d . . .
C6 C 0.10142(19) 0.21333(14) -0.13865(13) 0.0137(3) Uani 1 1 d . . .
C7 C 0.21429(19) 0.31226(13) -0.04514(13) 0.0138(3) Uani 1 1 d . . .
C8 C 0.2212(2) 0.30798(14) 0.07143(13) 0.0159(3) Uani 1 1 d . . .
H8 H 0.1483 0.2451 0.0903 0.019 Uiso 1 1 calc R . .
C9 C 0.33093(19) 0.39244(14) 0.16118(13) 0.0138(3) Uani 1 1 d . . .
C10 C 0.31506(19) 0.38240(13) 0.28394(13) 0.0136(3) Uani 1 1 d . . .
C11 C 0.45947(19) 0.36795(14) 0.35249(13) 0.0144(3) Uani 1 1 d . . .
C12 C 0.4449(2) 0.35144(14) 0.46267(13) 0.0156(3) Uani 1 1 d . . .
C13 C 0.2834(2) 0.35254(14) 0.50885(13) 0.0166(3) Uani 1 1 d . . .
C14 C 0.1379(2) 0.36910(14) 0.44419(13) 0.0157(3) Uani 1 1 d . . .
C15 C 0.15478(19) 0.38338(13) 0.33370(13) 0.0142(3) Uani 1 1 d . . .
C16 C 0.4722(2) 0.80067(15) 0.24414(14) 0.0196(3) Uani 1 1 d . . .
H16 H 0.4713 0.7204 0.2568 0.023 Uiso 1 1 calc R . .
C17 C 0.5410(2) 0.90698(16) 0.33164(15) 0.0241(3) Uani 1 1 d . . .
H17 H 0.5872 0.8996 0.4047 0.029 Uiso 1 1 calc R . .
C18 C 0.5433(2) 1.02508(17) 0.31366(17) 0.0296(4) Uani 1 1 d . . .
H18 H 0.5914 1.0980 0.3738 0.036 Uiso 1 1 calc R . .
C19 C 0.4748(3) 1.03480(17) 0.20759(18) 0.0318(4) Uani 1 1 d . . .
H19 H 0.4753 1.1152 0.1953 0.038 Uiso 1 1 calc R . .
C20 C 0.4048(2) 0.92884(16) 0.11811(16) 0.0249(4) Uani 1 1 d . . .
H20 H 0.3584 0.9366 0.0452 0.030 Uiso 1 1 calc R . .
C21 C 0.4039(2) 0.81164(15) 0.13706(14) 0.0172(3) Uani 1 1 d . . .
C22 C 0.2552(2) 0.70998(19) -0.05238(15) 0.0267(4) Uani 1 1 d . . .
H22A H 0.1585 0.7632 -0.0339 0.040 Uiso 1 1 calc R . .
H22B H 0.2099 0.6259 -0.1019 0.040 Uiso 1 1 calc R . .
H22C H 0.3398 0.7471 -0.0946 0.040 Uiso 1 1 calc R . .
F1 F 0.00014(12) 0.36210(8) -0.22779(8) 0.0193(2) Uani 1 1 d . . .
F2 F -0.15211(13) 0.18081(9) -0.41513(8) 0.0233(2) Uani 1 1 d . . .
F3 F -0.14230(14) -0.06447(9) -0.42647(8) 0.0262(2) Uani 1 1 d . . .
F4 F 0.01833(15) -0.12799(9) -0.24461(9) 0.0289(2) Uani 1 1 d . . .
F5 F 0.17574(13) 0.04859(9) -0.06002(8) 0.0225(2) Uani 1 1 d . . .
F6 F 0.61857(12) 0.36488(9) 0.31126(8) 0.0203(2) Uani 1 1 d . . .
F7 F 0.58613(12) 0.33468(9) 0.52480(8) 0.0215(2) Uani 1 1 d . . .
F8 F 0.26887(13) 0.33662(9) 0.61505(8) 0.0235(2) Uani 1 1 d . . .
F9 F -0.01859(12) 0.36943(9) 0.48813(8) 0.0215(2) Uani 1 1 d . . .
F10 F 0.00969(11) 0.39873(9) 0.27424(8) 0.01869(19) Uani 1 1 d . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.9229(11) 2_665 ?
Cu1 O1 1.9229(11) . ?
Cu1 O2 1.9445(11) 2_665 ?
Cu1 O2 1.9446(11) . ?
Cu1 O3 2.5768(13) . ?
O1 C7 1.2687(18) . ?
O2 C9 1.2695(18) . ?
O3 C21 1.3760(19) . ?
O3 C22 1.4328(19) . ?
C1 F1 1.3340(17) . ?
C1 C2 1.382(2) . ?
C1 C6 1.398(2) . ?
C2 F2 1.3346(18) . ?
C2 C3 1.383(2) . ?
C3 F3 1.3396(17) . ?
C3 C4 1.380(2) . ?
C4 F4 1.3421(18) . ?
C4 C5 1.380(2) . ?
C5 F5 1.3471(17) . ?
C5 C6 1.393(2) . ?
C6 C7 1.504(2) . ?
C7 C8 1.399(2) . ?
C8 C9 1.397(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.505(2) . ?
C10 C11 1.393(2) . ?
C10 C15 1.394(2) . ?
C11 F6 1.3408(17) . ?
C11 C12 1.383(2) . ?
C12 F7 1.3399(17) . ?
C12 C13 1.384(2) . ?
C13 F8 1.3333(17) . ?
C13 C14 1.381(2) . ?
C14 F9 1.3368(18) . ?
C14 C15 1.379(2) . ?
C15 F10 1.3413(17) . ?
C16 C17 1.381(2) . ?
C16 C21 1.395(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.394(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.379(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.393(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.390(2) . ?
C20 H20 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 180.0 2_665 . ?
O1 Cu1 O2 93.04(4) 2_665 2_665 ?
O1 Cu1 O2 86.96(4) . 2_665 ?
O1 Cu1 O2 86.96(4) 2_665 . ?
O1 Cu1 O2 93.04(4) . . ?
O2 Cu1 O2 180.0 2_665 . ?
O1 Cu1 O3 85.32(4) 2_665 . ?
O1 Cu1 O3 94.68(4) . . ?
O2 Cu1 O3 91.15(4) 2_665 . ?
O2 Cu1 O3 88.85(4) . . ?
C7 O1 Cu1 124.49(10) . . ?
C9 O2 Cu1 123.97(10) . . ?
C21 O3 C22 117.11(13) . . ?
C21 O3 Cu1 124.17(9) . . ?
C22 O3 Cu1 106.80(9) . . ?
F1 C1 C2 117.51(13) . . ?
F1 C1 C6 120.43(13) . . ?
C2 C1 C6 122.05(14) . . ?
F2 C2 C1 120.92(14) . . ?
F2 C2 C3 119.44(14) . . ?
C1 C2 C3 119.64(14) . . ?
F3 C3 C4 120.10(14) . . ?
F3 C3 C2 120.00(14) . . ?
C4 C3 C2 119.90(14) . . ?
F4 C4 C3 120.45(14) . . ?
F4 C4 C5 119.96(14) . . ?
C3 C4 C5 119.58(14) . . ?
F5 C5 C4 116.61(13) . . ?
F5 C5 C6 120.95(13) . . ?
C4 C5 C6 122.40(14) . . ?
C5 C6 C1 116.33(13) . . ?
C5 C6 C7 121.94(13) . . ?
C1 C6 C7 121.33(13) . . ?
O1 C7 C8 126.02(13) . . ?
O1 C7 C6 114.29(13) . . ?
C8 C7 C6 119.68(13) . . ?
C9 C8 C7 122.61(14) . . ?
C9 C8 H8 118.7 . . ?
C7 C8 H8 118.7 . . ?
O2 C9 C8 127.07(14) . . ?
O2 C9 C10 116.21(13) . . ?
C8 C9 C10 116.69(13) . . ?
C11 C10 C15 116.50(13) . . ?
C11 C10 C9 121.60(13) . . ?
C15 C10 C9 121.87(13) . . ?
F6 C11 C12 117.29(13) . . ?
F6 C11 C10 120.56(13) . . ?
C12 C11 C10 122.10(14) . . ?
F7 C12 C11 120.40(14) . . ?
F7 C12 C13 119.97(14) . . ?
C11 C12 C13 119.63(14) . . ?
F8 C13 C14 120.45(14) . . ?
F8 C13 C12 119.78(14) . . ?
C14 C13 C12 119.77(14) . . ?
F9 C14 C15 120.31(14) . . ?
F9 C14 C13 119.98(14) . . ?
C15 C14 C13 119.70(14) . . ?
F10 C15 C14 117.46(13) . . ?
F10 C15 C10 120.27(13) . . ?
C14 C15 C10 122.27(14) . . ?
C17 C16 C21 119.70(15) . . ?
C17 C16 H16 120.2 . . ?
C21 C16 H16 120.2 . . ?
C16 C17 C18 120.54(16) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C19 C18 C17 119.23(17) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C18 C19 C20 121.19(16) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C21 C20 C19 118.98(16) . . ?
C21 C20 H20 120.5 . . ?
C19 C20 H20 120.5 . . ?
O3 C21 C20 123.86(15) . . ?
O3 C21 C16 115.79(14) . . ?
C20 C21 C16 120.36(15) . . ?
O3 C22 H22A 109.5 . . ?
O3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 Cu1 O1 C7 157(29) 2_665 . . . ?
O2 Cu1 O1 C7 161.55(12) 2_665 . . . ?
O2 Cu1 O1 C7 -18.45(12) . . . . ?
O3 Cu1 O1 C7 -107.54(12) . . . . ?
O1 Cu1 O2 C9 -169.14(12) 2_665 . . . ?
O1 Cu1 O2 C9 10.86(12) . . . . ?
O2 Cu1 O2 C9 72(27) 2_665 . . . ?
O3 Cu1 O2 C9 105.49(12) . . . . ?
O1 Cu1 O3 C21 -13.43(11) 2_665 . . . ?
O1 Cu1 O3 C21 166.57(11) . . . . ?
O2 Cu1 O3 C21 -106.39(11) 2_665 . . . ?
O2 Cu1 O3 C21 73.61(11) . . . . ?
O1 Cu1 O3 C22 127.86(11) 2_665 . . . ?
O1 Cu1 O3 C22 -52.14(11) . . . . ?
O2 Cu1 O3 C22 34.91(11) 2_665 . . . ?
O2 Cu1 O3 C22 -145.09(11) . . . . ?
F1 C1 C2 F2 2.0(2) . . . . ?
C6 C1 C2 F2 -179.07(13) . . . . ?
F1 C1 C2 C3 -177.73(13) . . . . ?
C6 C1 C2 C3 1.2(2) . . . . ?
F2 C2 C3 F3 1.4(2) . . . . ?
C1 C2 C3 F3 -178.88(14) . . . . ?
F2 C2 C3 C4 -178.44(14) . . . . ?
C1 C2 C3 C4 1.3(2) . . . . ?
F3 C3 C4 F4 -0.3(2) . . . . ?
C2 C3 C4 F4 179.54(14) . . . . ?
F3 C3 C4 C5 178.74(14) . . . . ?
C2 C3 C4 C5 -1.4(2) . . . . ?
F4 C4 C5 F5 0.1(2) . . . . ?
C3 C4 C5 F5 -178.92(14) . . . . ?
F4 C4 C5 C6 178.11(14) . . . . ?
C3 C4 C5 C6 -0.9(2) . . . . ?
F5 C5 C6 C1 -178.85(13) . . . . ?
C4 C5 C6 C1 3.2(2) . . . . ?
F5 C5 C6 C7 8.3(2) . . . . ?
C4 C5 C6 C7 -169.65(14) . . . . ?
F1 C1 C6 C5 175.53(13) . . . . ?
C2 C1 C6 C5 -3.4(2) . . . . ?
F1 C1 C6 C7 -11.5(2) . . . . ?
C2 C1 C6 C7 169.56(14) . . . . ?
Cu1 O1 C7 C8 17.1(2) . . . . ?
Cu1 O1 C7 C6 -161.53(10) . . . . ?
C5 C6 C7 O1 135.01(15) . . . . ?
C1 C6 C7 O1 -37.5(2) . . . . ?
C5 C6 C7 C8 -43.7(2) . . . . ?
C1 C6 C7 C8 143.77(15) . . . . ?
O1 C7 C8 C9 -2.4(2) . . . . ?
C6 C7 C8 C9 176.16(14) . . . . ?
Cu1 O2 C9 C8 -1.2(2) . . . . ?
Cu1 O2 C9 C10 176.72(9) . . . . ?
C7 C8 C9 O2 -6.3(3) . . . . ?
C7 C8 C9 C10 175.73(14) . . . . ?
O2 C9 C10 C11 -52.36(19) . . . . ?
C8 C9 C10 C11 125.82(16) . . . . ?
O2 C9 C10 C15 129.54(15) . . . . ?
C8 C9 C10 C15 -52.3(2) . . . . ?
C15 C10 C11 F6 179.44(12) . . . . ?
C9 C10 C11 F6 1.2(2) . . . . ?
C15 C10 C11 C12 2.0(2) . . . . ?
C9 C10 C11 C12 -176.23(13) . . . . ?
F6 C11 C12 F7 0.8(2) . . . . ?
C10 C11 C12 F7 178.31(13) . . . . ?
F6 C11 C12 C13 -179.37(13) . . . . ?
C10 C11 C12 C13 -1.8(2) . . . . ?
F7 C12 C13 F8 -0.1(2) . . . . ?
C11 C12 C13 F8 179.99(13) . . . . ?
F7 C12 C13 C14 -179.62(13) . . . . ?
C11 C12 C13 C14 0.5(2) . . . . ?
F8 C13 C14 F9 0.1(2) . . . . ?
C12 C13 C14 F9 179.57(13) . . . . ?
F8 C13 C14 C15 -178.94(13) . . . . ?
C12 C13 C14 C15 0.5(2) . . . . ?
F9 C14 C15 F10 0.7(2) . . . . ?
C13 C14 C15 F10 179.76(13) . . . . ?
F9 C14 C15 C10 -179.36(13) . . . . ?
C13 C14 C15 C10 -0.3(2) . . . . ?
C11 C10 C15 F10 179.02(12) . . . . ?
C9 C10 C15 F10 -2.8(2) . . . . ?
C11 C10 C15 C14 -0.9(2) . . . . ?
C9 C10 C15 C14 177.30(13) . . . . ?
C21 C16 C17 C18 -0.2(3) . . . . ?
C16 C17 C18 C19 0.4(3) . . . . ?
C17 C18 C19 C20 -0.5(3) . . . . ?
C18 C19 C20 C21 0.3(3) . . . . ?
C22 O3 C21 C20 -5.2(2) . . . . ?
Cu1 O3 C21 C20 132.55(14) . . . . ?
C22 O3 C21 C16 175.07(14) . . . . ?
Cu1 O3 C21 C16 -47.19(18) . . . . ?
C19 C20 C21 O3 -179.73(16) . . . . ?
C19 C20 C21 C16 0.0(3) . . . . ?
C17 C16 C21 O3 179.69(14) . . . . ?
C17 C16 C21 C20 -0.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.055
_database_code_depnum_ccdc_archive 'CCDC 895479'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_101209b1
#TrackingRef 'web_deposit_cif_file_2_AkikoHori_1344479020.101209b1.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H2 Cu F20 O4, 2(C9 H12)'
_chemical_formula_sum            'C48 H26 Cu F20 O4'
_chemical_formula_weight         1110.24

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   14.845(3)
_cell_length_b                   31.844(7)
_cell_length_c                   10.082(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.011(2)
_cell_angle_gamma                90.00
_cell_volume                     4449.1(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    9955
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      27.67

_exptl_crystal_description       prismatic
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2220
_exptl_absorpt_coefficient_mu    0.621
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8602
_exptl_absorpt_correction_T_max  0.9181
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            24874
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_sigmaI/netI    0.0192
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.42
_diffrn_reflns_theta_max         27.48
_reflns_number_total             5067
_reflns_number_gt                4451
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0402P)²+5.2287P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5067
_refine_ls_number_parameters     334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0299
_refine_ls_wR_factor_ref         0.0822
_refine_ls_wR_factor_gt          0.0785
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.0000 0.084257(8) 0.2500 0.01534(8) Uani 1 2 d S . .
O1 O 0.09310(8) 0.04285(3) 0.35127(12) 0.0192(2) Uani 1 1 d . . .
O2 O 0.07988(8) 0.12550(3) 0.37651(11) 0.0180(2) Uani 1 1 d . . .
C1 C 0.25797(12) -0.01457(5) 0.44699(17) 0.0201(3) Uani 1 1 d . . .
C2 C 0.33594(12) -0.03631(5) 0.54002(18) 0.0236(3) Uani 1 1 d . . .
C3 C 0.32036(12) -0.06629(5) 0.62862(17) 0.0236(3) Uani 1 1 d . . .
C4 C 0.22791(13) -0.07465(5) 0.62230(17) 0.0223(3) Uani 1 1 d . . .
C5 C 0.15141(11) -0.05284(5) 0.52762(16) 0.0190(3) Uani 1 1 d . . .
C6 C 0.16385(11) -0.02197(5) 0.43829(16) 0.0172(3) Uani 1 1 d . . .
C7 C 0.08100(11) 0.00333(5) 0.34114(16) 0.0167(3) Uani 1 1 d . . .
C8 C 0.0000 -0.01782(7) 0.2500 0.0197(4) Uani 1 2 d S . .
H8 H 0.0000 -0.0476 0.2500 0.024 Uiso 1 2 calc SR . .
C9 C 0.23768(11) 0.18607(5) 0.51919(16) 0.0189(3) Uani 1 1 d . . .
C10 C 0.30210(11) 0.20810(5) 0.63169(17) 0.0211(3) Uani 1 1 d . . .
C11 C 0.26745(12) 0.23466(5) 0.71060(17) 0.0221(3) Uani 1 1 d . . .
C12 C 0.16942(12) 0.23976(5) 0.67564(17) 0.0214(3) Uani 1 1 d . . .
C13 C 0.10626(11) 0.21814(5) 0.56090(16) 0.0185(3) Uani 1 1 d . . .
C14 C 0.13821(11) 0.19056(5) 0.48082(15) 0.0158(3) Uani 1 1 d . . .
C15 C 0.06870(10) 0.16495(5) 0.36213(15) 0.0152(3) Uani 1 1 d . . .
C16 C 0.0000 0.18610(7) 0.2500 0.0179(4) Uani 1 2 d S . .
H16 H 0.0000 0.2159 0.2500 0.021 Uiso 1 2 calc SR . .
C17 C 0.29693(16) 0.10400(6) 0.75552(19) 0.0352(4) Uani 1 1 d . . .
C18 C 0.38430(14) 0.12015(6) 0.84556(19) 0.0311(4) Uani 1 1 d . . .
H18 H 0.4424 0.1112 0.8350 0.037 Uiso 1 1 calc R . .
C19 C 0.38858(13) 0.14901(6) 0.95060(18) 0.0279(4) Uani 1 1 d . . .
C20 C 0.30369(15) 0.16129(5) 0.96561(19) 0.0304(4) Uani 1 1 d . . .
H20 H 0.3059 0.1809 1.0378 0.037 Uiso 1 1 calc R . .
C21 C 0.21530(14) 0.14571(6) 0.8779(2) 0.0333(4) Uani 1 1 d . . .
C22 C 0.21276(14) 0.11728(6) 0.7730(2) 0.0352(5) Uani 1 1 d . . .
H22 H 0.1524 0.1066 0.7117 0.042 Uiso 1 1 calc R . .
C23 C 0.2950(3) 0.07259(8) 0.6419(3) 0.0683(9) Uani 1 1 d . . .
H23A H 0.3023 0.0441 0.6814 0.102 Uiso 1 1 calc R . .
H23B H 0.3480 0.0785 0.6084 0.102 Uiso 1 1 calc R . .
H23C H 0.2333 0.0748 0.5622 0.102 Uiso 1 1 calc R . .
C24 C 0.48359(17) 0.16692(8) 1.0475(2) 0.0499(6) Uani 1 1 d . . .
H24A H 0.5194 0.1453 1.1151 0.075 Uiso 1 1 calc R . .
H24B H 0.4715 0.1909 1.0995 0.075 Uiso 1 1 calc R . .
H24C H 0.5215 0.1761 0.9907 0.075 Uiso 1 1 calc R . .
C25 C 0.12276(19) 0.15954(9) 0.8968(3) 0.0653(8) Uani 1 1 d . . .
H25A H 0.1365 0.1668 0.9965 0.098 Uiso 1 1 calc R . .
H25B H 0.0757 0.1366 0.8691 0.098 Uiso 1 1 calc R . .
H25C H 0.0964 0.1841 0.8369 0.098 Uiso 1 1 calc R . .
F1 F 0.27594(7) 0.01396(3) 0.36176(11) 0.0283(2) Uani 1 1 d . . .
F2 F 0.42508(7) -0.02830(4) 0.54462(13) 0.0359(3) Uani 1 1 d . . .
F3 F 0.39469(8) -0.08681(3) 0.72053(12) 0.0338(3) Uani 1 1 d . . .
F4 F 0.21230(8) -0.10357(3) 0.70778(11) 0.0328(2) Uani 1 1 d . . .
F5 F 0.06193(7) -0.06173(3) 0.52600(10) 0.0260(2) Uani 1 1 d . . .
F6 F 0.27321(7) 0.16106(3) 0.44333(11) 0.0279(2) Uani 1 1 d . . .
F7 F 0.39722(7) 0.20445(3) 0.66362(11) 0.0299(2) Uani 1 1 d . . .
F8 F 0.32915(7) 0.25580(3) 0.81992(11) 0.0317(2) Uani 1 1 d . . .
F9 F 0.13604(8) 0.26490(3) 0.75406(11) 0.0339(3) Uani 1 1 d . . .
F10 F 0.01150(7) 0.22351(3) 0.53112(10) 0.0263(2) Uani 1 1 d . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O2 1.9164(11) . ?
Cu1 O2 1.9165(11) 2 ?
Cu1 O1 1.9181(11) 2 ?
Cu1 O1 1.9181(11) . ?
O1 C7 1.2701(18) . ?
O2 C15 1.2687(18) . ?
C1 F1 1.3413(18) . ?
C1 C2 1.386(2) . ?
C1 C6 1.388(2) . ?
C2 F2 1.332(2) . ?
C2 C3 1.382(2) . ?
C3 F3 1.3304(18) . ?
C3 C4 1.377(2) . ?
C4 F4 1.3371(19) . ?
C4 C5 1.381(2) . ?
C5 F5 1.3526(18) . ?
C5 C6 1.390(2) . ?
C6 C7 1.502(2) . ?
C7 C8 1.3970(18) . ?
C8 C7 1.3969(18) 2 ?
C8 H8 0.9500 . ?
C9 F6 1.3367(18) . ?
C9 C10 1.384(2) . ?
C9 C14 1.393(2) . ?
C10 F7 1.3361(18) . ?
C10 C11 1.381(2) . ?
C11 F8 1.3354(18) . ?
C11 C12 1.379(2) . ?
C12 F9 1.3387(19) . ?
C12 C13 1.383(2) . ?
C13 F10 1.3400(18) . ?
C13 C14 1.387(2) . ?
C14 C15 1.509(2) . ?
C15 C16 1.3947(18) . ?
C16 C15 1.3947(18) 2 ?
C16 H16 0.9500 . ?
C17 C18 1.388(3) . ?
C17 C22 1.389(3) . ?
C17 C23 1.513(3) . ?
C18 C19 1.386(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.379(3) . ?
C19 C24 1.510(3) . ?
C20 C21 1.385(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.382(3) . ?
C21 C25 1.518(3) . ?
C22 H22 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 O2 93.50(6) . 2 ?
O2 Cu1 O1 168.83(5) . 2 ?
O2 Cu1 O1 87.76(5) 2 2 ?
O2 Cu1 O1 87.76(5) . . ?
O2 Cu1 O1 168.83(5) 2 . ?
O1 Cu1 O1 93.15(7) 2 . ?
C7 O1 Cu1 125.74(10) . . ?
C15 O2 Cu1 125.32(10) . . ?
F1 C1 C2 117.53(14) . . ?
F1 C1 C6 120.08(14) . . ?
C2 C1 C6 122.38(15) . . ?
F2 C2 C3 120.27(15) . . ?
F2 C2 C1 120.41(15) . . ?
C3 C2 C1 119.32(15) . . ?
F3 C3 C4 120.07(16) . . ?
F3 C3 C2 120.01(16) . . ?
C4 C3 C2 119.91(15) . . ?
F4 C4 C3 120.24(15) . . ?
F4 C4 C5 120.17(15) . . ?
C3 C4 C5 119.59(15) . . ?
F5 C5 C4 117.64(14) . . ?
F5 C5 C6 119.89(14) . . ?
C4 C5 C6 122.45(15) . . ?
C1 C6 C5 116.34(14) . . ?
C1 C6 C7 121.36(14) . . ?
C5 C6 C7 122.27(14) . . ?
O1 C7 C8 126.45(15) . . ?
O1 C7 C6 114.82(13) . . ?
C8 C7 C6 118.73(14) . . ?
C7 C8 C7 122.4(2) 2 . ?
C7 C8 H8 118.8 2 . ?
C7 C8 H8 118.8 . . ?
F6 C9 C10 118.19(14) . . ?
F6 C9 C14 119.92(14) . . ?
C10 C9 C14 121.85(15) . . ?
F7 C10 C11 119.63(14) . . ?
F7 C10 C9 120.89(15) . . ?
C11 C10 C9 119.47(15) . . ?
F8 C11 C12 120.02(15) . . ?
F8 C11 C10 119.83(15) . . ?
C12 C11 C10 120.14(14) . . ?
F9 C12 C11 119.98(14) . . ?
F9 C12 C13 120.54(15) . . ?
C11 C12 C13 119.46(15) . . ?
F10 C13 C12 117.78(14) . . ?
F10 C13 C14 120.08(13) . . ?
C12 C13 C14 122.11(14) . . ?
C13 C14 C9 116.95(14) . . ?
C13 C14 C15 121.65(13) . . ?
C9 C14 C15 121.34(13) . . ?
O2 C15 C16 126.77(14) . . ?
O2 C15 C14 114.86(13) . . ?
C16 C15 C14 118.37(14) . . ?
C15 C16 C15 122.24(19) . 2 ?
C15 C16 H16 118.9 . . ?
C15 C16 H16 118.9 2 . ?
C18 C17 C22 118.45(17) . . ?
C18 C17 C23 120.0(2) . . ?
C22 C17 C23 121.6(2) . . ?
C19 C18 C17 121.43(18) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C20 C19 C18 118.58(17) . . ?
C20 C19 C24 120.02(19) . . ?
C18 C19 C24 121.39(19) . . ?
C19 C20 C21 121.49(17) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 H20 119.3 . . ?
C22 C21 C20 118.89(18) . . ?
C22 C21 C25 120.6(2) . . ?
C20 C21 C25 120.6(2) . . ?
C21 C22 C17 121.16(17) . . ?
C21 C22 H22 119.4 . . ?
C17 C22 H22 119.4 . . ?
C17 C23 H23A 109.5 . . ?
C17 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C17 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C19 C24 H24A 109.5 . . ?
C19 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C19 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C21 C25 H25A 109.5 . . ?
C21 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C21 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 Cu1 O1 C7 167.28(12) . . . . ?
O2 Cu1 O1 C7 -96.0(2) 2 . . . ?
O1 Cu1 O1 C7 -1.58(10) 2 . . . ?
O2 Cu1 O2 C15 1.47(10) 2 . . . ?
O1 Cu1 O2 C15 -94.7(2) 2 . . . ?
O1 Cu1 O2 C15 170.36(12) . . . . ?
F1 C1 C2 F2 1.0(2) . . . . ?
C6 C1 C2 F2 179.80(15) . . . . ?
F1 C1 C2 C3 -179.34(14) . . . . ?
C6 C1 C2 C3 -0.5(2) . . . . ?
F2 C2 C3 F3 1.1(2) . . . . ?
C1 C2 C3 F3 -178.64(15) . . . . ?
F2 C2 C3 C4 -179.40(15) . . . . ?
C1 C2 C3 C4 0.9(2) . . . . ?
F3 C3 C4 F4 -0.4(2) . . . . ?
C2 C3 C4 F4 -179.93(15) . . . . ?
F3 C3 C4 C5 179.29(14) . . . . ?
C2 C3 C4 C5 -0.3(2) . . . . ?
F4 C4 C5 F5 0.4(2) . . . . ?
C3 C4 C5 F5 -179.30(14) . . . . ?
F4 C4 C5 C6 178.83(14) . . . . ?
C3 C4 C5 C6 -0.9(2) . . . . ?
F1 C1 C6 C5 178.27(14) . . . . ?
C2 C1 C6 C5 -0.5(2) . . . . ?
F1 C1 C6 C7 -3.9(2) . . . . ?
C2 C1 C6 C7 177.27(14) . . . . ?
F5 C5 C6 C1 179.63(13) . . . . ?
C4 C5 C6 C1 1.2(2) . . . . ?
F5 C5 C6 C7 1.8(2) . . . . ?
C4 C5 C6 C7 -176.57(14) . . . . ?
Cu1 O1 C7 C8 3.3(2) . . . . ?
Cu1 O1 C7 C6 -176.91(9) . . . . ?
C1 C6 C7 O1 -49.7(2) . . . . ?
C5 C6 C7 O1 128.02(16) . . . . ?
C1 C6 C7 C8 130.13(14) . . . . ?
C5 C6 C7 C8 -52.20(19) . . . . ?
O1 C7 C8 C7 -1.82(11) . . . 2 ?
C6 C7 C8 C7 178.43(15) . . . 2 ?
F6 C9 C10 F7 0.0(2) . . . . ?
C14 C9 C10 F7 -177.62(14) . . . . ?
F6 C9 C10 C11 179.02(14) . . . . ?
C14 C9 C10 C11 1.4(2) . . . . ?
F7 C10 C11 F8 -1.4(2) . . . . ?
C9 C10 C11 F8 179.53(14) . . . . ?
F7 C10 C11 C12 177.80(14) . . . . ?
C9 C10 C11 C12 -1.3(2) . . . . ?
F8 C11 C12 F9 -2.1(2) . . . . ?
C10 C11 C12 F9 178.68(14) . . . . ?
F8 C11 C12 C13 179.08(14) . . . . ?
C10 C11 C12 C13 -0.1(2) . . . . ?
F9 C12 C13 F10 0.4(2) . . . . ?
C11 C12 C13 F10 179.24(14) . . . . ?
F9 C12 C13 C14 -177.37(14) . . . . ?
C11 C12 C13 C14 1.4(2) . . . . ?
F10 C13 C14 C9 -179.02(13) . . . . ?
C12 C13 C14 C9 -1.3(2) . . . . ?
F10 C13 C14 C15 -2.0(2) . . . . ?
C12 C13 C14 C15 175.81(14) . . . . ?
F6 C9 C14 C13 -177.73(14) . . . . ?
C10 C9 C14 C13 -0.2(2) . . . . ?
F6 C9 C14 C15 5.2(2) . . . . ?
C10 C9 C14 C15 -177.25(14) . . . . ?
Cu1 O2 C15 C16 -3.1(2) . . . . ?
Cu1 O2 C15 C14 176.83(9) . . . . ?
C13 C14 C15 O2 -121.02(16) . . . . ?
C9 C14 C15 O2 55.92(19) . . . . ?
C13 C14 C15 C16 58.92(19) . . . . ?
C9 C14 C15 C16 -124.14(14) . . . . ?
O2 C15 C16 C15 1.71(11) . . . 2 ?
C14 C15 C16 C15 -178.22(14) . . . 2 ?
C22 C17 C18 C19 -0.3(3) . . . . ?
C23 C17 C18 C19 179.89(18) . . . . ?
C17 C18 C19 C20 0.7(3) . . . . ?
C17 C18 C19 C24 -179.33(18) . . . . ?
C18 C19 C20 C21 -0.5(3) . . . . ?
C24 C19 C20 C21 179.51(17) . . . . ?
C19 C20 C21 C22 -0.1(3) . . . . ?
C19 C20 C21 C25 179.74(18) . . . . ?
C20 C21 C22 C17 0.6(3) . . . . ?
C25 C21 C22 C17 -179.26(18) . . . . ?
C18 C17 C22 C21 -0.4(3) . . . . ?
C23 C17 C22 C21 179.44(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.053
_database_code_depnum_ccdc_archive 'CCDC 895481'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_111106b2
#TrackingRef 'web_deposit_cif_file_3_AkikoHori_1344479020.111106b2.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H2 Cu F20 O4, C10 H14'
_chemical_formula_sum            'C40 H16 Cu F20 O4'
_chemical_formula_weight         1004.08

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.319(3)
_cell_length_b                   9.625(3)
_cell_length_c                   12.998(5)
_cell_angle_alpha                82.099(4)
_cell_angle_beta                 76.943(4)
_cell_angle_gamma                88.950(4)
_cell_volume                     883.4(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    100
_cell_measurement_reflns_used    2613
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      27.84

_exptl_crystal_description       prismatic
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.887
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             497
_exptl_absorpt_coefficient_mu    0.771
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8017
_exptl_absorpt_correction_T_max  0.9552
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            5012
_diffrn_reflns_av_R_equivalents  0.0134
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         27.47
_reflns_number_total             3814
_reflns_number_gt                3403
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0431P)²+0.4038P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3814
_refine_ls_number_parameters     297
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0322
_refine_ls_wR_factor_ref         0.0847
_refine_ls_wR_factor_gt          0.0816
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 1.0000 1.0000 0.0000 0.01273(10) Uani 1 2 d S . .
O1 O 0.78428(18) 0.88476(13) 0.06782(10) 0.0146(3) Uani 1 1 d . . .
O2 O 1.02359(18) 1.05922(14) 0.13198(10) 0.0161(3) Uani 1 1 d . . .
C1 C 0.3980(3) 0.77998(19) 0.14866(14) 0.0147(4) Uani 1 1 d . . .
C2 C 0.2469(3) 0.6878(2) 0.17502(15) 0.0166(4) Uani 1 1 d . . .
C3 C 0.2437(3) 0.5729(2) 0.25223(16) 0.0181(4) Uani 1 1 d . . .
C4 C 0.3893(3) 0.5520(2) 0.30357(15) 0.0177(4) Uani 1 1 d . . .
C5 C 0.5379(3) 0.6467(2) 0.27771(15) 0.0158(4) Uani 1 1 d . . .
C6 C 0.5468(2) 0.76217(19) 0.19942(14) 0.0132(4) Uani 1 1 d . . .
C7 C 0.7119(2) 0.86250(19) 0.16681(14) 0.0130(4) Uani 1 1 d . . .
C8 C 0.7683(3) 0.9240(2) 0.24651(14) 0.0155(4) Uani 1 1 d . . .
H8 H 0.7030 0.8997 0.3186 0.019 Uiso 1 1 calc R . .
C9 C 0.9170(2) 1.01960(19) 0.22316(14) 0.0137(4) Uani 1 1 d . . .
C10 C 0.9593(3) 1.08657(19) 0.31382(14) 0.0145(4) Uani 1 1 d . . .
C11 C 1.1252(3) 1.0641(2) 0.34768(14) 0.0154(4) Uani 1 1 d . . .
C12 C 1.1648(3) 1.1285(2) 0.42918(15) 0.0181(4) Uani 1 1 d . . .
C13 C 1.0356(3) 1.2188(2) 0.47865(15) 0.0199(4) Uani 1 1 d . . .
C14 C 0.8689(3) 1.2430(2) 0.44732(15) 0.0198(4) Uani 1 1 d . . .
C15 C 0.8316(3) 1.1759(2) 0.36680(15) 0.0166(4) Uani 1 1 d . . .
C16 C 0.2044(3) 0.5798(2) -0.11377(16) 0.0201(4) Uani 1 1 d . . .
H16A H 0.1096 0.5045 -0.0962 0.030 Uiso 1 1 calc R . .
H16B H 0.2576 0.5935 -0.1908 0.030 Uiso 1 1 calc R . .
H16C H 0.1461 0.6669 -0.0922 0.030 Uiso 1 1 calc R . .
C17 C 0.3581(3) 0.5406(2) -0.05545(14) 0.0151(4) Uani 1 1 d . . .
C18 C 0.3452(3) 0.4157(2) 0.01453(15) 0.0155(4) Uani 1 1 d . . .
H18 H 0.2376 0.3573 0.0248 0.019 Uiso 1 1 calc R . .
C19 C 0.4833(3) 0.37258(19) 0.07015(14) 0.0151(4) Uani 1 1 d . . .
C20 C 0.4597(3) 0.2361(2) 0.14432(16) 0.0206(4) Uani 1 1 d . . .
H20A H 0.4308 0.2554 0.2183 0.031 Uiso 1 1 calc R . .
H20B H 0.5760 0.1828 0.1306 0.031 Uiso 1 1 calc R . .
H20C H 0.3568 0.1813 0.1323 0.031 Uiso 1 1 calc R . .
F1 F 0.39483(15) 0.89025(12) 0.07423(9) 0.0193(2) Uani 1 1 d . . .
F2 F 0.10371(16) 0.70981(12) 0.12622(10) 0.0229(3) Uani 1 1 d . . .
F3 F 0.09927(17) 0.48172(13) 0.27700(10) 0.0268(3) Uani 1 1 d . . .
F4 F 0.38693(18) 0.43991(12) 0.37776(10) 0.0254(3) Uani 1 1 d . . .
F5 F 0.67760(16) 0.62230(12) 0.32879(9) 0.0222(3) Uani 1 1 d . . .
F6 F 1.25057(16) 0.97315(12) 0.30395(9) 0.0214(3) Uani 1 1 d . . .
F7 F 1.32284(17) 1.10029(14) 0.46266(9) 0.0264(3) Uani 1 1 d . . .
F8 F 1.07149(19) 1.28108(14) 0.55779(10) 0.0301(3) Uani 1 1 d . . .
F9 F 0.74372(19) 1.33045(14) 0.49470(10) 0.0321(3) Uani 1 1 d . . .
F10 F 0.66726(16) 1.20069(13) 0.33949(9) 0.0232(3) Uani 1 1 d . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.9148(13) 2_775 ?
Cu1 O1 1.9148(13) . ?
Cu1 O2 1.9245(14) . ?
Cu1 O2 1.9245(14) 2_775 ?
O1 C7 1.266(2) . ?
O2 C9 1.276(2) . ?
C1 F1 1.338(2) . ?
C1 C2 1.381(3) . ?
C1 C6 1.392(3) . ?
C2 F2 1.342(2) . ?
C2 C3 1.384(3) . ?
C3 F3 1.339(2) . ?
C3 C4 1.378(3) . ?
C4 F4 1.342(2) . ?
C4 C5 1.383(3) . ?
C5 F5 1.340(2) . ?
C5 C6 1.392(3) . ?
C6 C7 1.507(2) . ?
C7 C8 1.402(3) . ?
C8 C9 1.390(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.510(2) . ?
C10 C11 1.386(3) . ?
C10 C15 1.389(3) . ?
C11 F6 1.343(2) . ?
C11 C12 1.385(3) . ?
C12 F7 1.336(2) . ?
C12 C13 1.382(3) . ?
C13 F8 1.336(2) . ?
C13 C14 1.377(3) . ?
C14 F9 1.336(2) . ?
C14 C15 1.382(3) . ?
C15 F10 1.338(2) . ?
C16 C17 1.508(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.395(3) . ?
C17 C19 1.405(3) 2_665 ?
C18 C19 1.396(3) . ?
C18 H18 0.9500 . ?
C19 C17 1.405(3) 2_665 ?
C19 C20 1.506(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 180.00(5) 2_775 . ?
O1 Cu1 O2 87.16(5) 2_775 . ?
O1 Cu1 O2 92.84(5) . . ?
O1 Cu1 O2 92.84(5) 2_775 2_775 ?
O1 Cu1 O2 87.16(5) . 2_775 ?
O2 Cu1 O2 180.000(1) . 2_775 ?
C7 O1 Cu1 126.40(12) . . ?
C9 O2 Cu1 125.29(12) . . ?
F1 C1 C2 117.77(16) . . ?
F1 C1 C6 120.55(16) . . ?
C2 C1 C6 121.65(17) . . ?
F2 C2 C1 120.13(17) . . ?
F2 C2 C3 120.17(16) . . ?
C1 C2 C3 119.71(17) . . ?
F3 C3 C4 119.92(18) . . ?
F3 C3 C2 120.09(17) . . ?
C4 C3 C2 120.00(17) . . ?
F4 C4 C3 119.99(17) . . ?
F4 C4 C5 120.37(18) . . ?
C3 C4 C5 119.63(18) . . ?
F5 C5 C4 117.90(17) . . ?
F5 C5 C6 120.26(16) . . ?
C4 C5 C6 121.82(17) . . ?
C1 C6 C5 117.18(16) . . ?
C1 C6 C7 120.35(16) . . ?
C5 C6 C7 122.44(16) . . ?
O1 C7 C8 126.29(17) . . ?
O1 C7 C6 115.49(15) . . ?
C8 C7 C6 118.20(16) . . ?
C9 C8 C7 121.94(17) . . ?
C9 C8 H8 119.0 . . ?
C7 C8 H8 119.0 . . ?
O2 C9 C8 127.09(17) . . ?
O2 C9 C10 115.06(16) . . ?
C8 C9 C10 117.85(16) . . ?
C11 C10 C15 116.78(17) . . ?
C11 C10 C9 122.55(17) . . ?
C15 C10 C9 120.66(17) . . ?
F6 C11 C12 117.77(17) . . ?
F6 C11 C10 119.99(16) . . ?
C12 C11 C10 122.20(18) . . ?
F7 C12 C13 120.02(17) . . ?
F7 C12 C11 120.64(18) . . ?
C13 C12 C11 119.30(18) . . ?
F8 C13 C14 120.01(19) . . ?
F8 C13 C12 119.96(19) . . ?
C14 C13 C12 120.03(18) . . ?
F9 C14 C13 120.27(17) . . ?
F9 C14 C15 120.20(18) . . ?
C13 C14 C15 119.53(18) . . ?
F10 C15 C14 117.81(17) . . ?
F10 C15 C10 120.05(17) . . ?
C14 C15 C10 122.14(18) . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C17 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C19 118.54(17) . 2_665 ?
C18 C17 C16 120.13(17) . . ?
C19 C17 C16 121.34(17) 2_665 . ?
C17 C18 C19 123.00(17) . . ?
C17 C18 H18 118.5 . . ?
C19 C18 H18 118.5 . . ?
C18 C19 C17 118.47(17) . 2_665 ?
C18 C19 C20 119.97(17) . . ?
C17 C19 C20 121.57(17) 2_665 . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 Cu1 O1 C7 167(24) 2_775 . . . ?
O2 Cu1 O1 C7 -3.70(15) . . . . ?
O2 Cu1 O1 C7 176.30(15) 2_775 . . . ?
O1 Cu1 O2 C9 -179.23(15) 2_775 . . . ?
O1 Cu1 O2 C9 0.77(15) . . . . ?
O2 Cu1 O2 C9 -37(98) 2_775 . . . ?
F1 C1 C2 F2 0.3(3) . . . . ?
C6 C1 C2 F2 178.47(16) . . . . ?
F1 C1 C2 C3 -179.49(16) . . . . ?
C6 C1 C2 C3 -1.3(3) . . . . ?
F2 C2 C3 F3 1.3(3) . . . . ?
C1 C2 C3 F3 -178.89(17) . . . . ?
F2 C2 C3 C4 -178.77(17) . . . . ?
C1 C2 C3 C4 1.0(3) . . . . ?
F3 C3 C4 F4 0.5(3) . . . . ?
C2 C3 C4 F4 -179.39(17) . . . . ?
F3 C3 C4 C5 -179.92(17) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
F4 C4 C5 F5 0.1(3) . . . . ?
C3 C4 C5 F5 -179.49(17) . . . . ?
F4 C4 C5 C6 178.46(17) . . . . ?
C3 C4 C5 C6 -1.1(3) . . . . ?
F1 C1 C6 C5 178.53(16) . . . . ?
C2 C1 C6 C5 0.4(3) . . . . ?
F1 C1 C6 C7 -3.5(3) . . . . ?
C2 C1 C6 C7 178.39(17) . . . . ?
F5 C5 C6 C1 179.16(16) . . . . ?
C4 C5 C6 C1 0.8(3) . . . . ?
F5 C5 C6 C7 1.2(3) . . . . ?
C4 C5 C6 C7 -177.13(17) . . . . ?
Cu1 O1 C7 C8 4.0(3) . . . . ?
Cu1 O1 C7 C6 -177.51(11) . . . . ?
C1 C6 C7 O1 -50.3(2) . . . . ?
C5 C6 C7 O1 127.61(19) . . . . ?
C1 C6 C7 C8 128.40(19) . . . . ?
C5 C6 C7 C8 -53.7(2) . . . . ?
O1 C7 C8 C9 -0.3(3) . . . . ?
C6 C7 C8 C9 -178.81(17) . . . . ?
Cu1 O2 C9 C8 2.2(3) . . . . ?
Cu1 O2 C9 C10 -177.25(12) . . . . ?
C7 C8 C9 O2 -3.0(3) . . . . ?
C7 C8 C9 C10 176.38(17) . . . . ?
O2 C9 C10 C11 -65.4(2) . . . . ?
C8 C9 C10 C11 115.1(2) . . . . ?
O2 C9 C10 C15 114.0(2) . . . . ?
C8 C9 C10 C15 -65.5(2) . . . . ?
C15 C10 C11 F6 176.43(16) . . . . ?
C9 C10 C11 F6 -4.2(3) . . . . ?
C15 C10 C11 C12 -1.0(3) . . . . ?
C9 C10 C11 C12 178.42(17) . . . . ?
F6 C11 C12 F7 -0.1(3) . . . . ?
C10 C11 C12 F7 177.38(17) . . . . ?
F6 C11 C12 C13 -177.65(16) . . . . ?
C10 C11 C12 C13 -0.2(3) . . . . ?
F7 C12 C13 F8 2.0(3) . . . . ?
C11 C12 C13 F8 179.61(17) . . . . ?
F7 C12 C13 C14 -177.09(17) . . . . ?
C11 C12 C13 C14 0.5(3) . . . . ?
F8 C13 C14 F9 1.0(3) . . . . ?
C12 C13 C14 F9 -179.84(17) . . . . ?
F8 C13 C14 C15 -178.72(17) . . . . ?
C12 C13 C14 C15 0.4(3) . . . . ?
F9 C14 C15 F10 -0.6(3) . . . . ?
C13 C14 C15 F10 179.17(17) . . . . ?
F9 C14 C15 C10 178.58(17) . . . . ?
C13 C14 C15 C10 -1.7(3) . . . . ?
C11 C10 C15 F10 -178.94(16) . . . . ?
C9 C10 C15 F10 1.6(3) . . . . ?
C11 C10 C15 C14 1.9(3) . . . . ?
C9 C10 C15 C14 -177.50(17) . . . . ?
C19 C17 C18 C19 -0.4(3) 2_665 . . . ?
C16 C17 C18 C19 179.35(17) . . . . ?
C17 C18 C19 C17 0.4(3) . . . 2_665 ?
C17 C18 C19 C20 -179.93(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.940
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.940
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.065
_database_code_depnum_ccdc_archive 'CCDC 895482'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_110418a1
#TrackingRef 'web_deposit_cif_file_4_AkikoHori_1344479020.110418a1.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H2 Cu F20 O4, 2(C8 H10)'
_chemical_formula_sum            'C46 H22 Cu F20 O4'
_chemical_formula_weight         1082.19

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   9.8602(12)
_cell_length_b                   16.961(2)
_cell_length_c                   24.948(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4172.3(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    9936
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      27.81

_exptl_crystal_description       prismatic
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.723
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2156
_exptl_absorpt_coefficient_mu    0.660
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8266
_exptl_absorpt_correction_T_max  0.9075
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            22088
_diffrn_reflns_av_R_equivalents  0.0165
_diffrn_reflns_av_sigmaI/netI    0.0219
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.39
_diffrn_reflns_theta_max         27.48
_reflns_number_total             8931
_reflns_number_gt                8347
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0384P)²+0.6599P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_number_reflns         8931
_refine_ls_number_parameters     644
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0250
_refine_ls_wR_factor_ref         0.0642
_refine_ls_wR_factor_gt          0.0623
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.64150(2) 0.833927(11) 0.522268(10) 0.01726(5) Uani 1 1 d . . .
O1 O 0.69923(13) 0.91214(7) 0.47187(5) 0.0199(3) Uani 1 1 d . . .
O2 O 0.58405(13) 0.91014(7) 0.57426(5) 0.0197(3) Uani 1 1 d . . .
O3 O 0.55258(14) 0.75635(7) 0.56511(5) 0.0199(3) Uani 1 1 d . . .
O4 O 0.72676(14) 0.75796(7) 0.47686(5) 0.0209(3) Uani 1 1 d . . .
C1 C 0.71539(19) 1.02165(11) 0.38173(8) 0.0221(4) Uani 1 1 d . . .
C2 C 0.7633(2) 1.06827(12) 0.34039(8) 0.0255(4) Uani 1 1 d . . .
C3 C 0.85223(19) 1.12911(12) 0.35139(8) 0.0233(4) Uani 1 1 d . . .
C4 C 0.8907(2) 1.14359(11) 0.40330(8) 0.0219(4) Uani 1 1 d . . .
C5 C 0.83883(18) 1.09754(11) 0.44386(8) 0.0189(4) Uani 1 1 d . . .
C6 C 0.75102(18) 1.03547(10) 0.43491(8) 0.0177(4) Uani 1 1 d . . .
C7 C 0.69448(18) 0.98605(10) 0.47954(7) 0.0177(4) Uani 1 1 d . . .
C8 C 0.64039(18) 1.02492(9) 0.52416(10) 0.0197(3) Uani 1 1 d . . .
H8 H 0.6408 1.0809 0.5247 0.024 Uiso 1 1 calc R . .
C9 C 0.58579(18) 0.98434(10) 0.56795(7) 0.0170(4) Uani 1 1 d . . .
C10 C 0.52330(18) 1.03116(10) 0.61294(7) 0.0164(3) Uani 1 1 d . . .
C11 C 0.54464(19) 1.01080(11) 0.66607(8) 0.0189(4) Uani 1 1 d . . .
C12 C 0.48579(19) 1.05192(11) 0.70772(8) 0.0220(4) Uani 1 1 d . . .
C13 C 0.4017(2) 1.11502(12) 0.69726(8) 0.0239(4) Uani 1 1 d . . .
C14 C 0.37631(19) 1.13624(12) 0.64471(9) 0.0229(4) Uani 1 1 d . . .
C15 C 0.43769(18) 1.09518(11) 0.60383(8) 0.0202(4) Uani 1 1 d . . .
C16 C 0.49595(19) 0.63495(11) 0.64938(8) 0.0218(4) Uani 1 1 d . . .
C17 C 0.4144(2) 0.59299(12) 0.68449(8) 0.0258(4) Uani 1 1 d . . .
C18 C 0.3063(2) 0.55063(12) 0.66470(9) 0.0272(4) Uani 1 1 d . . .
C19 C 0.2820(2) 0.54838(12) 0.61075(9) 0.0271(4) Uani 1 1 d . . .
C20 C 0.3656(2) 0.58972(11) 0.57619(8) 0.0222(4) Uani 1 1 d . . .
C21 C 0.47377(18) 0.63380(10) 0.59489(8) 0.0183(4) Uani 1 1 d . . .
C22 C 0.55924(18) 0.68237(11) 0.55746(8) 0.0178(4) Uani 1 1 d . . .
C23 C 0.63556(19) 0.64345(10) 0.51861(10) 0.0217(3) Uani 1 1 d . . .
H23 H 0.6340 0.5875 0.5177 0.026 Uiso 1 1 calc R . .
C24 C 0.71410(18) 0.68369(10) 0.48105(8) 0.0179(4) Uani 1 1 d . . .
C25 C 0.79157(18) 0.63563(10) 0.44081(8) 0.0180(4) Uani 1 1 d . . .
C26 C 0.7640(2) 0.64068(11) 0.38655(8) 0.0232(4) Uani 1 1 d . . .
C27 C 0.8337(2) 0.59629(13) 0.34902(8) 0.0258(4) Uani 1 1 d . . .
C28 C 0.9347(2) 0.54609(11) 0.36562(8) 0.0228(4) Uani 1 1 d . . .
C29 C 0.9653(2) 0.54025(11) 0.41922(9) 0.0245(4) Uani 1 1 d . . .
C30 C 0.8936(2) 0.58415(11) 0.45617(8) 0.0210(4) Uani 1 1 d . . .
C31 C 0.2218(2) 0.77746(12) 0.65184(9) 0.0274(4) Uani 1 1 d . . .
C32 C 0.1485(2) 0.74110(13) 0.69240(9) 0.0276(5) Uani 1 1 d . . .
H32 H 0.1716 0.7520 0.7286 0.033 Uiso 1 1 calc R . .
C33 C 0.0423(2) 0.68909(13) 0.68185(9) 0.0289(4) Uani 1 1 d . . .
C34 C 0.0109(2) 0.67309(12) 0.62879(10) 0.0320(5) Uani 1 1 d . . .
H34 H -0.0606 0.6375 0.6205 0.038 Uiso 1 1 calc R . .
C35 C 0.0833(2) 0.70872(13) 0.58767(10) 0.0334(5) Uani 1 1 d . . .
H35 H 0.0608 0.6978 0.5514 0.040 Uiso 1 1 calc R . .
C36 C 0.1882(2) 0.76022(12) 0.59940(9) 0.0294(5) Uani 1 1 d . . .
H36 H 0.2377 0.7840 0.5710 0.035 Uiso 1 1 calc R . .
C37 C 0.3347(3) 0.83442(14) 0.66500(12) 0.0419(6) Uani 1 1 d . . .
H37A H 0.3926 0.8415 0.6334 0.063 Uiso 1 1 calc R . .
H37B H 0.3889 0.8134 0.6947 0.063 Uiso 1 1 calc R . .
H37C H 0.2958 0.8853 0.6755 0.063 Uiso 1 1 calc R . .
C38 C -0.0368(3) 0.65066(15) 0.72683(11) 0.0439(6) Uani 1 1 d . . .
H38A H -0.0146 0.5944 0.7284 0.066 Uiso 1 1 calc R . .
H38B H -0.1341 0.6571 0.7203 0.066 Uiso 1 1 calc R . .
H38C H -0.0127 0.6756 0.7610 0.066 Uiso 1 1 calc R . .
C39 C 0.5024(2) 0.20817(14) 0.35024(11) 0.0370(5) Uani 1 1 d . . .
C40 C 0.5996(2) 0.26565(13) 0.33856(10) 0.0328(5) Uani 1 1 d . . .
H40 H 0.6122 0.2815 0.3024 0.039 Uiso 1 1 calc R . .
C41 C 0.6783(2) 0.30032(12) 0.37817(10) 0.0318(5) Uani 1 1 d . . .
C42 C 0.6568(2) 0.27709(13) 0.43127(10) 0.0330(5) Uani 1 1 d . . .
H42 H 0.7082 0.3003 0.4593 0.040 Uiso 1 1 calc R . .
C43 C 0.5608(2) 0.22045(13) 0.44280(10) 0.0356(5) Uani 1 1 d . . .
H43 H 0.5470 0.2047 0.4789 0.043 Uiso 1 1 calc R . .
C44 C 0.4848(2) 0.18653(13) 0.40294(11) 0.0376(6) Uani 1 1 d . . .
H44 H 0.4191 0.1476 0.4118 0.045 Uiso 1 1 calc R . .
C45 C 0.4161(3) 0.1720(2) 0.30650(16) 0.0682(10) Uani 1 1 d . . .
H45A H 0.4564 0.1220 0.2950 0.102 Uiso 1 1 calc R . .
H45B H 0.4116 0.2082 0.2759 0.102 Uiso 1 1 calc R . .
H45C H 0.3245 0.1625 0.3202 0.102 Uiso 1 1 calc R . .
C46 C 0.7821(3) 0.36228(15) 0.36444(14) 0.0558(8) Uani 1 1 d . . .
H46A H 0.8731 0.3391 0.3658 0.084 Uiso 1 1 calc R . .
H46B H 0.7762 0.4057 0.3903 0.084 Uiso 1 1 calc R . .
H46C H 0.7647 0.3824 0.3283 0.084 Uiso 1 1 calc R . .
F1 F 0.62641(13) 0.96478(9) 0.36958(5) 0.0343(3) Uani 1 1 d . . .
F2 F 0.72224(13) 1.05559(9) 0.29005(5) 0.0394(3) Uani 1 1 d . . .
F3 F 0.89989(13) 1.17406(7) 0.31190(5) 0.0322(3) Uani 1 1 d . . .
F4 F 0.97631(13) 1.20272(7) 0.41444(5) 0.0323(3) Uani 1 1 d . . .
F5 F 0.87809(12) 1.11554(7) 0.49453(5) 0.0266(3) Uani 1 1 d . . .
F6 F 0.62746(12) 0.95102(7) 0.67908(5) 0.0255(3) Uani 1 1 d . . .
F7 F 0.50975(13) 1.03052(7) 0.75863(5) 0.0308(3) Uani 1 1 d . . .
F8 F 0.34432(13) 1.15448(8) 0.73719(6) 0.0352(3) Uani 1 1 d . . .
F9 F 0.29060(12) 1.19511(7) 0.63396(5) 0.0314(3) Uani 1 1 d . . .
F10 F 0.40711(12) 1.11747(7) 0.55344(5) 0.0251(2) Uani 1 1 d . . .
F11 F 0.60038(14) 0.67559(8) 0.66967(5) 0.0336(3) Uani 1 1 d . . .
F12 F 0.43718(15) 0.59558(9) 0.73736(5) 0.0443(3) Uani 1 1 d . . .
F13 F 0.22457(15) 0.51161(8) 0.69839(5) 0.0406(3) Uani 1 1 d . . .
F14 F 0.17440(14) 0.50891(8) 0.59175(6) 0.0425(3) Uani 1 1 d . . .
F15 F 0.33584(12) 0.58887(7) 0.52355(6) 0.0337(3) Uani 1 1 d . . .
F16 F 0.66547(15) 0.68837(10) 0.36921(5) 0.0421(4) Uani 1 1 d . . .
F17 F 0.80263(15) 0.60129(9) 0.29707(5) 0.0464(4) Uani 1 1 d . . .
F18 F 1.00361(14) 0.50281(8) 0.33018(5) 0.0338(3) Uani 1 1 d . . .
F19 F 1.06699(15) 0.49312(8) 0.43521(6) 0.0434(4) Uani 1 1 d . . .
F20 F 0.92723(13) 0.57771(8) 0.50816(5) 0.0341(3) Uani 1 1 d . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O3 1.9085(13) . ?
Cu1 O4 1.9106(13) . ?
Cu1 O1 1.9144(13) . ?
Cu1 O2 1.9168(13) . ?
O1 C7 1.269(2) . ?
O2 C9 1.268(2) . ?
O3 C22 1.271(2) . ?
O4 C24 1.270(2) . ?
C1 F1 1.339(2) . ?
C1 C2 1.383(3) . ?
C1 C6 1.392(3) . ?
C2 F2 1.337(2) . ?
C2 C3 1.381(3) . ?
C3 F3 1.332(2) . ?
C3 C4 1.372(3) . ?
C4 F4 1.340(2) . ?
C4 C5 1.377(3) . ?
C5 F5 1.357(2) . ?
C5 C6 1.381(3) . ?
C6 C7 1.501(2) . ?
C7 C8 1.399(3) . ?
C8 C9 1.399(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.507(2) . ?
C10 C11 1.386(3) . ?
C10 C15 1.394(2) . ?
C11 F6 1.342(2) . ?
C11 C12 1.379(3) . ?
C12 F7 1.342(2) . ?
C12 C13 1.379(3) . ?
C13 F8 1.327(2) . ?
C13 C14 1.382(3) . ?
C14 F9 1.335(2) . ?
C14 C15 1.375(3) . ?
C15 F10 1.347(2) . ?
C16 F11 1.339(2) . ?
C16 C21 1.377(3) . ?
C16 C17 1.386(3) . ?
C17 F12 1.339(2) . ?
C17 C18 1.377(3) . ?
C18 F13 1.340(2) . ?
C18 C19 1.368(3) . ?
C19 F14 1.341(2) . ?
C19 C20 1.383(3) . ?
C20 F15 1.346(2) . ?
C20 C21 1.384(3) . ?
C21 C22 1.504(3) . ?
C22 C23 1.393(3) . ?
C23 C24 1.394(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.502(3) . ?
C25 C26 1.383(3) . ?
C25 C30 1.386(3) . ?
C26 F16 1.336(2) . ?
C26 C27 1.384(3) . ?
C27 F17 1.334(2) . ?
C27 C28 1.374(3) . ?
C28 F18 1.335(2) . ?
C28 C29 1.375(3) . ?
C29 F19 1.343(2) . ?
C29 C30 1.380(3) . ?
C30 F20 1.343(2) . ?
C31 C36 1.381(3) . ?
C31 C32 1.388(3) . ?
C31 C37 1.510(3) . ?
C32 C33 1.395(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.386(3) . ?
C33 C38 1.514(3) . ?
C34 C35 1.388(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.385(3) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 C44 1.376(4) . ?
C39 C40 1.398(3) . ?
C39 C45 1.513(4) . ?
C40 C41 1.387(4) . ?
C40 H40 0.9500 . ?
C41 C42 1.398(3) . ?
C41 C46 1.507(3) . ?
C42 C43 1.379(3) . ?
C42 H42 0.9500 . ?
C43 C44 1.372(4) . ?
C43 H43 0.9500 . ?
C44 H44 0.9500 . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 0.9800 . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Cu1 O4 93.97(5) . . ?
O3 Cu1 O1 169.16(6) . . ?
O4 Cu1 O1 86.96(6) . . ?
O3 Cu1 O2 87.15(5) . . ?
O4 Cu1 O2 170.42(6) . . ?
O1 Cu1 O2 93.73(5) . . ?
C7 O1 Cu1 125.07(12) . . ?
C9 O2 Cu1 125.53(12) . . ?
C22 O3 Cu1 124.95(12) . . ?
C24 O4 Cu1 125.22(12) . . ?
F1 C1 C2 117.84(18) . . ?
F1 C1 C6 120.17(17) . . ?
C2 C1 C6 121.87(17) . . ?
F2 C2 C3 119.94(18) . . ?
F2 C2 C1 120.32(18) . . ?
C3 C2 C1 119.73(18) . . ?
F3 C3 C4 119.90(18) . . ?
F3 C3 C2 120.31(19) . . ?
C4 C3 C2 119.79(18) . . ?
F4 C4 C3 120.27(18) . . ?
F4 C4 C5 120.41(18) . . ?
C3 C4 C5 119.31(18) . . ?
F5 C5 C4 116.81(16) . . ?
F5 C5 C6 120.06(17) . . ?
C4 C5 C6 123.13(18) . . ?
C5 C6 C1 116.14(17) . . ?
C5 C6 C7 122.58(17) . . ?
C1 C6 C7 121.27(16) . . ?
O1 C7 C8 126.83(17) . . ?
O1 C7 C6 115.22(16) . . ?
C8 C7 C6 117.94(15) . . ?
C9 C8 C7 122.42(14) . . ?
C9 C8 H8 118.8 . . ?
C7 C8 H8 118.8 . . ?
O2 C9 C8 126.18(16) . . ?
O2 C9 C10 115.15(15) . . ?
C8 C9 C10 118.67(15) . . ?
C11 C10 C15 116.22(17) . . ?
C11 C10 C9 121.27(16) . . ?
C15 C10 C9 122.47(17) . . ?
F6 C11 C12 117.11(17) . . ?
F6 C11 C10 120.81(16) . . ?
C12 C11 C10 122.05(17) . . ?
F7 C12 C13 119.66(17) . . ?
F7 C12 C11 120.15(18) . . ?
C13 C12 C11 120.19(18) . . ?
F8 C13 C12 120.40(19) . . ?
F8 C13 C14 120.23(19) . . ?
C12 C13 C14 119.37(18) . . ?
F9 C14 C15 120.55(19) . . ?
F9 C14 C13 119.98(18) . . ?
C15 C14 C13 119.45(18) . . ?
F10 C15 C14 116.84(16) . . ?
F10 C15 C10 120.41(17) . . ?
C14 C15 C10 122.70(18) . . ?
F11 C16 C21 120.19(17) . . ?
F11 C16 C17 118.14(18) . . ?
C21 C16 C17 121.64(18) . . ?
F12 C17 C18 120.01(18) . . ?
F12 C17 C16 120.58(19) . . ?
C18 C17 C16 119.36(19) . . ?
F13 C18 C19 119.9(2) . . ?
F13 C18 C17 119.9(2) . . ?
C19 C18 C17 120.21(19) . . ?
F14 C19 C18 120.03(19) . . ?
F14 C19 C20 120.27(19) . . ?
C18 C19 C20 119.64(19) . . ?
F15 C20 C19 118.22(17) . . ?
F15 C20 C21 120.19(17) . . ?
C19 C20 C21 121.53(19) . . ?
C16 C21 C20 117.58(17) . . ?
C16 C21 C22 121.08(17) . . ?
C20 C21 C22 121.25(17) . . ?
O3 C22 C23 126.88(17) . . ?
O3 C22 C21 114.76(16) . . ?
C23 C22 C21 118.36(16) . . ?
C22 C23 C24 122.38(15) . . ?
C22 C23 H23 118.8 . . ?
C24 C23 H23 118.8 . . ?
O4 C24 C23 126.54(17) . . ?
O4 C24 C25 115.67(16) . . ?
C23 C24 C25 117.78(15) . . ?
C26 C25 C30 116.88(17) . . ?
C26 C25 C24 121.37(17) . . ?
C30 C25 C24 121.75(17) . . ?
F16 C26 C25 119.81(17) . . ?
F16 C26 C27 118.11(18) . . ?
C25 C26 C27 122.07(18) . . ?
F17 C27 C28 119.88(18) . . ?
F17 C27 C26 120.59(18) . . ?
C28 C27 C26 119.53(18) . . ?
F18 C28 C27 120.67(18) . . ?
F18 C28 C29 119.53(18) . . ?
C27 C28 C29 119.80(17) . . ?
F19 C29 C28 119.74(18) . . ?
F19 C29 C30 120.35(19) . . ?
C28 C29 C30 119.89(18) . . ?
F20 C30 C29 118.33(17) . . ?
F20 C30 C25 119.83(17) . . ?
C29 C30 C25 121.82(19) . . ?
C36 C31 C32 118.2(2) . . ?
C36 C31 C37 121.2(2) . . ?
C32 C31 C37 120.6(2) . . ?
C31 C32 C33 122.3(2) . . ?
C31 C32 H32 118.8 . . ?
C33 C32 H32 118.8 . . ?
C34 C33 C32 118.1(2) . . ?
C34 C33 C38 120.6(2) . . ?
C32 C33 C38 121.3(2) . . ?
C33 C34 C35 120.4(2) . . ?
C33 C34 H34 119.8 . . ?
C35 C34 H34 119.8 . . ?
C36 C35 C34 120.2(2) . . ?
C36 C35 H35 119.9 . . ?
C34 C35 H35 119.9 . . ?
C31 C36 C35 120.9(2) . . ?
C31 C36 H36 119.6 . . ?
C35 C36 H36 119.6 . . ?
C31 C37 H37A 109.5 . . ?
C31 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C31 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C33 C38 H38A 109.5 . . ?
C33 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C33 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C44 C39 C40 118.2(2) . . ?
C44 C39 C45 120.6(3) . . ?
C40 C39 C45 121.2(3) . . ?
C41 C40 C39 122.0(2) . . ?
C41 C40 H40 119.0 . . ?
C39 C40 H40 119.0 . . ?
C40 C41 C42 118.1(2) . . ?
C40 C41 C46 120.9(2) . . ?
C42 C41 C46 121.0(2) . . ?
C43 C42 C41 119.9(2) . . ?
C43 C42 H42 120.1 . . ?
C41 C42 H42 120.1 . . ?
C44 C43 C42 121.1(2) . . ?
C44 C43 H43 119.5 . . ?
C42 C43 H43 119.5 . . ?
C43 C44 C39 120.8(2) . . ?
C43 C44 H44 119.6 . . ?
C39 C44 H44 119.6 . . ?
C39 C45 H45A 109.5 . . ?
C39 C45 H45B 109.5 . . ?
H45A C45 H45B 109.5 . . ?
C39 C45 H45C 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
C41 C46 H46A 109.5 . . ?
C41 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C41 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 Cu1 O1 C7 95.7(3) . . . . ?
O4 Cu1 O1 C7 -168.99(15) . . . . ?
O2 Cu1 O1 C7 1.44(16) . . . . ?
O3 Cu1 O2 C9 -166.00(15) . . . . ?
O4 Cu1 O2 C9 97.0(3) . . . . ?
O1 Cu1 O2 C9 3.18(15) . . . . ?
O4 Cu1 O3 C22 -1.80(16) . . . . ?
O1 Cu1 O3 C22 92.8(3) . . . . ?
O2 Cu1 O3 C22 -172.27(15) . . . . ?
O3 Cu1 O4 C24 0.07(16) . . . . ?
O1 Cu1 O4 C24 -169.11(15) . . . . ?
O2 Cu1 O4 C24 96.5(4) . . . . ?
F1 C1 C2 F2 -0.7(3) . . . . ?
C6 C1 C2 F2 -176.95(18) . . . . ?
F1 C1 C2 C3 178.11(18) . . . . ?
C6 C1 C2 C3 1.9(3) . . . . ?
F2 C2 C3 F3 -1.6(3) . . . . ?
C1 C2 C3 F3 179.52(17) . . . . ?
F2 C2 C3 C4 177.86(18) . . . . ?
C1 C2 C3 C4 -1.0(3) . . . . ?
F3 C3 C4 F4 -0.1(3) . . . . ?
C2 C3 C4 F4 -179.64(18) . . . . ?
F3 C3 C4 C5 178.86(17) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
F4 C4 C5 F5 0.4(3) . . . . ?
C3 C4 C5 F5 -178.64(17) . . . . ?
F4 C4 C5 C6 -179.53(17) . . . . ?
C3 C4 C5 C6 1.5(3) . . . . ?
F5 C5 C6 C1 179.51(16) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
F5 C5 C6 C7 0.5(3) . . . . ?
C4 C5 C6 C7 -179.60(17) . . . . ?
F1 C1 C6 C5 -177.22(17) . . . . ?
C2 C1 C6 C5 -1.1(3) . . . . ?
F1 C1 C6 C7 1.8(3) . . . . ?
C2 C1 C6 C7 177.92(18) . . . . ?
Cu1 O1 C7 C8 -3.8(3) . . . . ?
Cu1 O1 C7 C6 177.57(11) . . . . ?
C5 C6 C7 O1 -133.51(19) . . . . ?
C1 C6 C7 O1 47.5(2) . . . . ?
C5 C6 C7 C8 47.7(3) . . . . ?
C1 C6 C7 C8 -131.26(19) . . . . ?
O1 C7 C8 C9 1.6(3) . . . . ?
C6 C7 C8 C9 -179.72(17) . . . . ?
Cu1 O2 C9 C8 -5.9(3) . . . . ?
Cu1 O2 C9 C10 174.62(11) . . . . ?
C7 C8 C9 O2 3.7(3) . . . . ?
C7 C8 C9 C10 -176.89(17) . . . . ?
O2 C9 C10 C11 40.9(2) . . . . ?
C8 C9 C10 C11 -138.54(19) . . . . ?
O2 C9 C10 C15 -136.81(18) . . . . ?
C8 C9 C10 C15 43.7(2) . . . . ?
C15 C10 C11 F6 -178.68(15) . . . . ?
C9 C10 C11 F6 3.4(3) . . . . ?
C15 C10 C11 C12 -0.6(3) . . . . ?
C9 C10 C11 C12 -178.52(17) . . . . ?
F6 C11 C12 F7 -1.5(3) . . . . ?
C10 C11 C12 F7 -179.61(17) . . . . ?
F6 C11 C12 C13 178.72(17) . . . . ?
C10 C11 C12 C13 0.6(3) . . . . ?
F7 C12 C13 F8 -0.1(3) . . . . ?
C11 C12 C13 F8 179.65(17) . . . . ?
F7 C12 C13 C14 -179.32(17) . . . . ?
C11 C12 C13 C14 0.5(3) . . . . ?
F8 C13 C14 F9 -2.0(3) . . . . ?
C12 C13 C14 F9 177.18(17) . . . . ?
F8 C13 C14 C15 179.37(17) . . . . ?
C12 C13 C14 C15 -1.4(3) . . . . ?
F9 C14 C15 F10 0.1(3) . . . . ?
C13 C14 C15 F10 178.73(17) . . . . ?
F9 C14 C15 C10 -177.18(17) . . . . ?
C13 C14 C15 C10 1.4(3) . . . . ?
C11 C10 C15 F10 -177.60(16) . . . . ?
C9 C10 C15 F10 0.3(3) . . . . ?
C11 C10 C15 C14 -0.4(3) . . . . ?
C9 C10 C15 C14 177.46(17) . . . . ?
F11 C16 C17 F12 2.3(3) . . . . ?
C21 C16 C17 F12 -179.38(18) . . . . ?
F11 C16 C17 C18 -179.96(18) . . . . ?
C21 C16 C17 C18 -1.7(3) . . . . ?
F12 C17 C18 F13 -0.4(3) . . . . ?
C16 C17 C18 F13 -178.16(18) . . . . ?
F12 C17 C18 C19 179.43(19) . . . . ?
C16 C17 C18 C19 1.7(3) . . . . ?
F13 C18 C19 F14 1.8(3) . . . . ?
C17 C18 C19 F14 -178.11(18) . . . . ?
F13 C18 C19 C20 179.06(17) . . . . ?
C17 C18 C19 C20 -0.8(3) . . . . ?
F14 C19 C20 F15 -0.1(3) . . . . ?
C18 C19 C20 F15 -177.42(19) . . . . ?
F14 C19 C20 C21 177.11(18) . . . . ?
C18 C19 C20 C21 -0.2(3) . . . . ?
F11 C16 C21 C20 178.95(17) . . . . ?
C17 C16 C21 C20 0.7(3) . . . . ?
F11 C16 C21 C22 -4.4(3) . . . . ?
C17 C16 C21 C22 177.32(17) . . . . ?
F15 C20 C21 C16 177.42(17) . . . . ?
C19 C20 C21 C16 0.2(3) . . . . ?
F15 C20 C21 C22 0.8(3) . . . . ?
C19 C20 C21 C22 -176.38(18) . . . . ?
Cu1 O3 C22 C23 2.9(3) . . . . ?
Cu1 O3 C22 C21 -176.75(12) . . . . ?
C16 C21 C22 O3 -61.6(2) . . . . ?
C20 C21 C22 O3 114.9(2) . . . . ?
C16 C21 C22 C23 118.7(2) . . . . ?
C20 C21 C22 C23 -64.8(2) . . . . ?
O3 C22 C23 C24 -1.9(3) . . . . ?
C21 C22 C23 C24 177.77(18) . . . . ?
Cu1 O4 C24 C23 0.8(3) . . . . ?
Cu1 O4 C24 C25 -179.74(12) . . . . ?
C22 C23 C24 O4 -0.2(3) . . . . ?
C22 C23 C24 C25 -179.64(18) . . . . ?
O4 C24 C25 C26 -63.1(2) . . . . ?
C23 C24 C25 C26 116.4(2) . . . . ?
O4 C24 C25 C30 117.0(2) . . . . ?
C23 C24 C25 C30 -63.4(2) . . . . ?
C30 C25 C26 F16 179.01(18) . . . . ?
C24 C25 C26 F16 -0.9(3) . . . . ?
C30 C25 C26 C27 0.5(3) . . . . ?
C24 C25 C26 C27 -179.42(18) . . . . ?
F16 C26 C27 F17 0.0(3) . . . . ?
C25 C26 C27 F17 178.56(19) . . . . ?
F16 C26 C27 C28 -179.4(2) . . . . ?
C25 C26 C27 C28 -0.8(3) . . . . ?
F17 C27 C28 F18 0.9(3) . . . . ?
C26 C27 C28 F18 -179.81(18) . . . . ?
F17 C27 C28 C29 -179.16(19) . . . . ?
C26 C27 C28 C29 0.2(3) . . . . ?
F18 C28 C29 F19 2.2(3) . . . . ?
C27 C28 C29 F19 -177.84(19) . . . . ?
F18 C28 C29 C30 -179.30(18) . . . . ?
C27 C28 C29 C30 0.7(3) . . . . ?
F19 C29 C30 F20 -0.7(3) . . . . ?
C28 C29 C30 F20 -179.23(18) . . . . ?
F19 C29 C30 C25 177.48(18) . . . . ?
C28 C29 C30 C25 -1.1(3) . . . . ?
C26 C25 C30 F20 178.62(18) . . . . ?
C24 C25 C30 F20 -1.5(3) . . . . ?
C26 C25 C30 C29 0.5(3) . . . . ?
C24 C25 C30 C29 -179.66(18) . . . . ?
C36 C31 C32 C33 -0.8(3) . . . . ?
C37 C31 C32 C33 179.0(2) . . . . ?
C31 C32 C33 C34 0.7(3) . . . . ?
C31 C32 C33 C38 -179.5(2) . . . . ?
C32 C33 C34 C35 -0.5(3) . . . . ?
C38 C33 C34 C35 179.7(2) . . . . ?
C33 C34 C35 C36 0.4(3) . . . . ?
C32 C31 C36 C35 0.7(3) . . . . ?
C37 C31 C36 C35 -179.1(2) . . . . ?
C34 C35 C36 C31 -0.5(3) . . . . ?
C44 C39 C40 C41 0.6(3) . . . . ?
C45 C39 C40 C41 179.0(2) . . . . ?
C39 C40 C41 C42 -0.9(3) . . . . ?
C39 C40 C41 C46 -179.9(2) . . . . ?
C40 C41 C42 C43 0.8(3) . . . . ?
C46 C41 C42 C43 179.8(2) . . . . ?
C41 C42 C43 C44 -0.4(3) . . . . ?
C42 C43 C44 C39 0.0(3) . . . . ?
C40 C39 C44 C43 -0.1(3) . . . . ?
C45 C39 C44 C43 -178.6(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.043
_database_code_depnum_ccdc_archive 'CCDC 895483'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_110609b1
#TrackingRef 'web_deposit_cif_file_5_AkikoHori_1344479020.110609b1.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C46 H22 Cu F20 O8'
_chemical_formula_sum            'C46 H22 Cu F20 O8'
_chemical_formula_weight         1146.19

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.7727(17)
_cell_length_b                   12.309(3)
_cell_length_c                   12.672(3)
_cell_angle_alpha                65.030(2)
_cell_angle_beta                 85.208(2)
_cell_angle_gamma                79.032(2)
_cell_volume                     1079.0(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    100
_cell_measurement_reflns_used    5975
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      27.88

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.764
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             571
_exptl_absorpt_coefficient_mu    0.650
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8810
_exptl_absorpt_correction_T_max  0.9088
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;


_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            11966
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.67
_diffrn_reflns_theta_max         27.46
_reflns_number_total             4780
_reflns_number_gt                4149
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0362P)²+0.5776P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4780
_refine_ls_number_parameters     342
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0299
_refine_ls_wR_factor_ref         0.0785
_refine_ls_wR_factor_gt          0.0743
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 1.0000 0.0000 0.5000 0.01415(8) Uani 1 2 d S . .
O1 O 0.92509(15) -0.00783(10) 0.65196(10) 0.0165(2) Uani 1 1 d . . .
O2 O 0.81582(15) 0.13287(10) 0.42327(9) 0.0158(2) Uani 1 1 d . . .
O3 O 1.19987(16) 0.15474(11) 0.48077(10) 0.0213(3) Uani 1 1 d . . .
O4 O 0.92483(17) 0.44801(11) 0.12850(10) 0.0225(3) Uani 1 1 d . . .
C1 C 0.7178(2) -0.05189(15) 0.86978(15) 0.0187(3) Uani 1 1 d . . .
C2 C 0.6961(2) -0.08066(17) 0.98732(15) 0.0238(4) Uani 1 1 d . . .
C3 C 0.7435(2) -0.00641(18) 1.03254(14) 0.0250(4) Uani 1 1 d . . .
C4 C 0.8129(2) 0.09501(16) 0.96107(15) 0.0221(4) Uani 1 1 d . . .
C5 C 0.8327(2) 0.12284(15) 0.84365(15) 0.0180(3) Uani 1 1 d . . .
C6 C 0.7865(2) 0.05039(14) 0.79511(14) 0.0148(3) Uani 1 1 d . . .
C7 C 0.8172(2) 0.07514(14) 0.66844(13) 0.0137(3) Uani 1 1 d . . .
C8 C 0.7262(2) 0.18117(14) 0.58454(14) 0.0156(3) Uani 1 1 d . . .
H8 H 0.6595 0.2404 0.6079 0.019 Uiso 1 1 calc R . .
C9 C 0.7301(2) 0.20321(14) 0.46619(14) 0.0144(3) Uani 1 1 d . . .
C10 C 0.6259(2) 0.31710(14) 0.37894(14) 0.0145(3) Uani 1 1 d . . .
C11 C 0.5486(2) 0.31522(15) 0.28401(14) 0.0170(3) Uani 1 1 d . . .
C12 C 0.4688(2) 0.42060(16) 0.19478(14) 0.0191(3) Uani 1 1 d . . .
C13 C 0.4643(2) 0.53128(15) 0.19886(14) 0.0195(3) Uani 1 1 d . . .
C14 C 0.5370(2) 0.53646(15) 0.29170(15) 0.0186(3) Uani 1 1 d . . .
C15 C 0.6147(2) 0.43074(15) 0.38069(14) 0.0162(3) Uani 1 1 d . . .
C16 C 1.1461(2) 0.27626(15) 0.41136(14) 0.0178(3) Uani 1 1 d . . .
C17 C 1.0772(2) 0.29931(15) 0.30424(14) 0.0176(3) Uani 1 1 d . . .
H17 H 1.0786 0.2345 0.2819 0.021 Uiso 1 1 calc R . .
C18 C 1.0067(2) 0.41731(15) 0.23080(14) 0.0178(3) Uani 1 1 d . . .
C19 C 1.0136(2) 0.51395(16) 0.26085(15) 0.0208(4) Uani 1 1 d . . .
H19 H 0.9677 0.5953 0.2099 0.025 Uiso 1 1 calc R . .
C20 C 1.0881(2) 0.48889(16) 0.36542(15) 0.0219(4) Uani 1 1 d . . .
H20 H 1.0946 0.5544 0.3852 0.026 Uiso 1 1 calc R . .
C21 C 1.1542(2) 0.37041(16) 0.44317(15) 0.0204(4) Uani 1 1 d . . .
H21 H 1.2032 0.3545 0.5155 0.024 Uiso 1 1 calc R . .
C22 C 1.2670(3) 0.12423(18) 0.59363(15) 0.0260(4) Uani 1 1 d . . .
H22A H 1.3722 0.1603 0.5851 0.039 Uiso 1 1 calc R . .
H22B H 1.2968 0.0356 0.6352 0.039 Uiso 1 1 calc R . .
H22C H 1.1779 0.1559 0.6377 0.039 Uiso 1 1 calc R . .
C23 C 0.9244(3) 0.35262(16) 0.09209(15) 0.0236(4) Uani 1 1 d . . .
H23A H 1.0452 0.3196 0.0789 0.035 Uiso 1 1 calc R . .
H23B H 0.8577 0.3851 0.0197 0.035 Uiso 1 1 calc R . .
H23C H 0.8701 0.2879 0.1527 0.035 Uiso 1 1 calc R . .
F1 F 0.66844(15) -0.12429(10) 0.82797(9) 0.0271(2) Uani 1 1 d . . .
F2 F 0.62864(16) -0.17959(11) 1.05763(10) 0.0377(3) Uani 1 1 d . . .
F3 F 0.72241(17) -0.03403(12) 1.14670(9) 0.0393(3) Uani 1 1 d . . .
F4 F 0.86477(16) 0.16427(11) 1.00630(10) 0.0335(3) Uani 1 1 d . . .
F5 F 0.90411(15) 0.22102(9) 0.77638(9) 0.0262(2) Uani 1 1 d . . .
F6 F 0.54681(13) 0.21030(9) 0.27688(9) 0.0224(2) Uani 1 1 d . . .
F7 F 0.39643(14) 0.41527(10) 0.10530(9) 0.0254(2) Uani 1 1 d . . .
F8 F 0.38840(14) 0.63375(9) 0.11267(9) 0.0273(2) Uani 1 1 d . . .
F9 F 0.53362(14) 0.64448(9) 0.29526(9) 0.0255(2) Uani 1 1 d . . .
F10 F 0.68525(13) 0.44159(9) 0.46813(8) 0.0204(2) Uani 1 1 d . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O2 1.9154(11) . ?
Cu1 O2 1.9154(11) 2_756 ?
Cu1 O1 1.9323(12) 2_756 ?
Cu1 O1 1.9323(12) . ?
Cu1 O3 2.6023(13) . ?
O1 C7 1.2709(19) . ?
O2 C9 1.2676(19) . ?
O3 C16 1.378(2) . ?
O3 C22 1.434(2) . ?
O4 C18 1.364(2) . ?
O4 C23 1.432(2) . ?
C1 F1 1.3359(19) . ?
C1 C2 1.381(2) . ?
C1 C6 1.390(2) . ?
C2 F2 1.342(2) . ?
C2 C3 1.380(3) . ?
C3 F3 1.342(2) . ?
C3 C4 1.375(3) . ?
C4 F4 1.342(2) . ?
C4 C5 1.381(2) . ?
C5 F5 1.342(2) . ?
C5 C6 1.387(2) . ?
C6 C7 1.509(2) . ?
C7 C8 1.392(2) . ?
C8 C9 1.406(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.501(2) . ?
C10 C15 1.394(2) . ?
C10 C11 1.399(2) . ?
C11 F6 1.3349(19) . ?
C11 C12 1.385(2) . ?
C12 F7 1.3380(19) . ?
C12 C13 1.379(2) . ?
C13 F8 1.3393(19) . ?
C13 C14 1.377(2) . ?
C14 F9 1.3446(19) . ?
C14 C15 1.380(2) . ?
C15 F10 1.3420(18) . ?
C16 C21 1.391(2) . ?
C16 C17 1.396(2) . ?
C17 C18 1.384(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.405(2) . ?
C19 C20 1.379(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.396(3) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 O2 180.0 . 2_756 ?
O2 Cu1 O1 87.44(5) . 2_756 ?
O2 Cu1 O1 92.56(5) 2_756 2_756 ?
O2 Cu1 O1 92.56(5) . . ?
O2 Cu1 O1 87.44(5) 2_756 . ?
O1 Cu1 O1 179.999(1) 2_756 . ?
O2 Cu1 O3 89.48(5) . . ?
O2 Cu1 O3 90.52(5) 2_756 . ?
O1 Cu1 O3 90.26(4) 2_756 . ?
O1 Cu1 O3 89.74(4) . . ?
C7 O1 Cu1 123.94(10) . . ?
C9 O2 Cu1 125.41(10) . . ?
C16 O3 C22 117.28(13) . . ?
C16 O3 Cu1 118.99(10) . . ?
C22 O3 Cu1 108.57(10) . . ?
C18 O4 C23 117.17(13) . . ?
F1 C1 C2 118.33(15) . . ?
F1 C1 C6 119.95(15) . . ?
C2 C1 C6 121.71(16) . . ?
F2 C2 C3 119.81(16) . . ?
F2 C2 C1 120.65(17) . . ?
C3 C2 C1 119.55(16) . . ?
F3 C3 C4 120.15(17) . . ?
F3 C3 C2 119.71(17) . . ?
C4 C3 C2 120.14(16) . . ?
F4 C4 C3 119.84(16) . . ?
F4 C4 C5 120.59(17) . . ?
C3 C4 C5 119.55(16) . . ?
F5 C5 C4 118.25(15) . . ?
F5 C5 C6 119.80(15) . . ?
C4 C5 C6 121.92(16) . . ?
C5 C6 C1 117.12(15) . . ?
C5 C6 C7 122.66(14) . . ?
C1 C6 C7 120.13(14) . . ?
O1 C7 C8 127.51(15) . . ?
O1 C7 C6 113.84(13) . . ?
C8 C7 C6 118.63(14) . . ?
C7 C8 C9 121.98(14) . . ?
C7 C8 H8 119.0 . . ?
C9 C8 H8 119.0 . . ?
O2 C9 C8 125.38(15) . . ?
O2 C9 C10 114.31(14) . . ?
C8 C9 C10 120.31(14) . . ?
C15 C10 C11 116.45(15) . . ?
C15 C10 C9 122.85(14) . . ?
C11 C10 C9 120.42(14) . . ?
F6 C11 C12 117.09(15) . . ?
F6 C11 C10 120.83(14) . . ?
C12 C11 C10 122.06(15) . . ?
F7 C12 C13 120.15(15) . . ?
F7 C12 C11 120.38(15) . . ?
C13 C12 C11 119.46(15) . . ?
F8 C13 C14 120.01(15) . . ?
F8 C13 C12 119.92(15) . . ?
C14 C13 C12 120.07(15) . . ?
F9 C14 C13 120.04(15) . . ?
F9 C14 C15 120.00(15) . . ?
C13 C14 C15 119.96(15) . . ?
F10 C15 C14 117.28(15) . . ?
F10 C15 C10 120.71(14) . . ?
C14 C15 C10 121.97(15) . . ?
O3 C16 C21 124.42(15) . . ?
O3 C16 C17 114.31(14) . . ?
C21 C16 C17 121.26(16) . . ?
C18 C17 C16 119.49(15) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
O4 C18 C17 123.93(15) . . ?
O4 C18 C19 115.83(15) . . ?
C17 C18 C19 120.23(15) . . ?
C20 C19 C18 118.93(16) . . ?
C20 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
C19 C20 C21 122.10(16) . . ?
C19 C20 H20 119.0 . . ?
C21 C20 H20 119.0 . . ?
C16 C21 C20 117.89(16) . . ?
C16 C21 H21 121.1 . . ?
C20 C21 H21 121.1 . . ?
O3 C22 H22A 109.5 . . ?
O3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O4 C23 H23A 109.5 . . ?
O4 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O4 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 Cu1 O1 C7 -13.99(13) . . . . ?
O2 Cu1 O1 C7 166.01(13) 2_756 . . . ?
O1 Cu1 O1 C7 93(24) 2_756 . . . ?
O3 Cu1 O1 C7 75.48(12) . . . . ?
O2 Cu1 O2 C9 -68(33) 2_756 . . . ?
O1 Cu1 O2 C9 -160.47(13) 2_756 . . . ?
O1 Cu1 O2 C9 19.53(13) . . . . ?
O3 Cu1 O2 C9 -70.18(13) . . . . ?
O2 Cu1 O3 C16 -10.63(11) . . . . ?
O2 Cu1 O3 C16 169.37(11) 2_756 . . . ?
O1 Cu1 O3 C16 76.81(11) 2_756 . . . ?
O1 Cu1 O3 C16 -103.19(11) . . . . ?
O2 Cu1 O3 C22 127.01(11) . . . . ?
O2 Cu1 O3 C22 -52.99(11) 2_756 . . . ?
O1 Cu1 O3 C22 -145.55(11) 2_756 . . . ?
O1 Cu1 O3 C22 34.45(11) . . . . ?
F1 C1 C2 F2 0.6(3) . . . . ?
C6 C1 C2 F2 179.66(16) . . . . ?
F1 C1 C2 C3 -179.03(15) . . . . ?
C6 C1 C2 C3 0.0(3) . . . . ?
F2 C2 C3 F3 0.3(3) . . . . ?
C1 C2 C3 F3 179.94(16) . . . . ?
F2 C2 C3 C4 179.92(16) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
F3 C3 C4 F4 2.2(3) . . . . ?
C2 C3 C4 F4 -177.50(16) . . . . ?
F3 C3 C4 C5 -179.55(15) . . . . ?
C2 C3 C4 C5 0.8(3) . . . . ?
F4 C4 C5 F5 -0.4(2) . . . . ?
C3 C4 C5 F5 -178.65(15) . . . . ?
F4 C4 C5 C6 177.49(15) . . . . ?
C3 C4 C5 C6 -0.8(3) . . . . ?
F5 C5 C6 C1 178.20(14) . . . . ?
C4 C5 C6 C1 0.4(2) . . . . ?
F5 C5 C6 C7 1.6(2) . . . . ?
C4 C5 C6 C7 -176.24(15) . . . . ?
F1 C1 C6 C5 179.03(14) . . . . ?
C2 C1 C6 C5 0.0(2) . . . . ?
F1 C1 C6 C7 -4.3(2) . . . . ?
C2 C1 C6 C7 176.74(15) . . . . ?
Cu1 O1 C7 C8 3.9(2) . . . . ?
Cu1 O1 C7 C6 -177.19(10) . . . . ?
C5 C6 C7 O1 115.66(17) . . . . ?
C1 C6 C7 O1 -60.9(2) . . . . ?
C5 C6 C7 C8 -65.4(2) . . . . ?
C1 C6 C7 C8 118.13(17) . . . . ?
O1 C7 C8 C9 7.2(3) . . . . ?
C6 C7 C8 C9 -171.62(14) . . . . ?
Cu1 O2 C9 C8 -15.1(2) . . . . ?
Cu1 O2 C9 C10 165.47(10) . . . . ?
C7 C8 C9 O2 -1.2(3) . . . . ?
C7 C8 C9 C10 178.19(14) . . . . ?
O2 C9 C10 C15 -138.86(16) . . . . ?
C8 C9 C10 C15 41.7(2) . . . . ?
O2 C9 C10 C11 34.7(2) . . . . ?
C8 C9 C10 C11 -144.70(16) . . . . ?
C15 C10 C11 F6 -177.44(14) . . . . ?
C9 C10 C11 F6 8.6(2) . . . . ?
C15 C10 C11 C12 1.6(2) . . . . ?
C9 C10 C11 C12 -172.45(15) . . . . ?
F6 C11 C12 F7 -1.0(2) . . . . ?
C10 C11 C12 F7 179.94(15) . . . . ?
F6 C11 C12 C13 178.88(15) . . . . ?
C10 C11 C12 C13 -0.1(3) . . . . ?
F7 C12 C13 F8 -0.5(2) . . . . ?
C11 C12 C13 F8 179.60(15) . . . . ?
F7 C12 C13 C14 179.22(15) . . . . ?
C11 C12 C13 C14 -0.7(3) . . . . ?
F8 C13 C14 F9 -0.7(2) . . . . ?
C12 C13 C14 F9 179.56(15) . . . . ?
F8 C13 C14 C15 179.76(15) . . . . ?
C12 C13 C14 C15 0.1(3) . . . . ?
F9 C14 C15 F10 -0.3(2) . . . . ?
C13 C14 C15 F10 179.19(14) . . . . ?
F9 C14 C15 C10 -178.04(14) . . . . ?
C13 C14 C15 C10 1.5(3) . . . . ?
C11 C10 C15 F10 -179.86(14) . . . . ?
C9 C10 C15 F10 -6.0(2) . . . . ?
C11 C10 C15 C14 -2.2(2) . . . . ?
C9 C10 C15 C14 171.63(15) . . . . ?
C22 O3 C16 C21 0.6(2) . . . . ?
Cu1 O3 C16 C21 134.67(14) . . . . ?
C22 O3 C16 C17 -178.09(15) . . . . ?
Cu1 O3 C16 C17 -44.03(17) . . . . ?
O3 C16 C17 C18 175.17(14) . . . . ?
C21 C16 C17 C18 -3.6(3) . . . . ?
C23 O4 C18 C17 -4.8(2) . . . . ?
C23 O4 C18 C19 176.50(15) . . . . ?
C16 C17 C18 O4 -174.99(15) . . . . ?
C16 C17 C18 C19 3.6(2) . . . . ?
O4 C18 C19 C20 177.37(15) . . . . ?
C17 C18 C19 C20 -1.4(3) . . . . ?
C18 C19 C20 C21 -1.1(3) . . . . ?
O3 C16 C21 C20 -177.43(15) . . . . ?
C17 C16 C21 C20 1.2(2) . . . . ?
C19 C20 C21 C16 1.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.969
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.969
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.607
_refine_diff_density_rms         0.056


_database_code_depnum_ccdc_archive 'CCDC 895484'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_110202a2
#TrackingRef 'web_deposit_cif_file_0_AkikoHori_1344479419.110202a2.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H6 Cu F16 O4'
_chemical_formula_sum            'C30 H6 Cu F16 O4'
_chemical_formula_weight         797.90

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   12.3918(8)
_cell_length_b                   10.5445(6)
_cell_length_c                   10.1291(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.1060(10)
_cell_angle_gamma                90.00
_cell_volume                     1323.28(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7139
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      27.92

_exptl_crystal_description       prismatic
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    2.003
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             782
_exptl_absorpt_coefficient_mu    0.980
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8873
_exptl_absorpt_correction_T_max  0.9712
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            14400
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_sigmaI/netI    0.0154
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.54
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3002
_reflns_number_gt                2693
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0298P)²+0.9686P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3002
_refine_ls_number_parameters     232
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0272
_refine_ls_wR_factor_ref         0.0699
_refine_ls_wR_factor_gt          0.0676
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 1.0000 1.0000 0.0000 0.01537(8) Uani 1 2 d S . .
O1 O 0.85219(9) 1.05017(11) 0.02673(12) 0.0200(2) Uani 1 1 d . . .
O2 O 0.96374(9) 0.82388(10) -0.01458(11) 0.0165(2) Uani 1 1 d . . .
C1 C 0.62029(13) 1.12721(16) 0.02038(16) 0.0181(3) Uani 1 1 d . . .
C2 C 0.52269(13) 1.17711(15) 0.05818(17) 0.0188(3) Uani 1 1 d . . .
C3 C 0.47146(13) 1.13480(16) 0.17057(17) 0.0198(3) Uani 1 1 d . . .
H3 H 0.4044 1.1697 0.1965 0.024 Uiso 1 1 calc R . .
C4 C 0.52114(14) 1.04055(16) 0.24308(16) 0.0196(3) Uani 1 1 d . . .
C5 C 0.61899(13) 0.99003(15) 0.20555(17) 0.0182(3) Uani 1 1 d . . .
C6 C 0.67083(13) 1.03171(15) 0.09321(17) 0.0170(3) Uani 1 1 d . . .
C7 C 0.77578(13) 0.97312(15) 0.04990(17) 0.0173(3) Uani 1 1 d . . .
C8 C 0.77856(13) 0.84212(16) 0.03927(17) 0.0190(3) Uani 1 1 d . . .
H8 H 0.7146 0.7955 0.0554 0.023 Uiso 1 1 calc R . .
C9 C 0.87160(12) 0.77601(15) 0.00577(15) 0.0154(3) Uani 1 1 d . . .
C10 C 0.86357(12) 0.63454(15) -0.00788(16) 0.0159(3) Uani 1 1 d . . .
C11 C 0.90823(13) 0.57126(15) -0.11450(16) 0.0172(3) Uani 1 1 d . . .
C12 C 0.90162(14) 0.44061(16) -0.12599(17) 0.0204(3) Uani 1 1 d . . .
C13 C 0.85005(14) 0.36759(16) -0.03415(19) 0.0235(4) Uani 1 1 d . . .
H13 H 0.8453 0.2781 -0.0434 0.028 Uiso 1 1 calc R . .
C14 C 0.80565(14) 0.42888(17) 0.0716(2) 0.0258(4) Uani 1 1 d . . .
C15 C 0.81247(14) 0.55932(17) 0.08548(18) 0.0215(4) Uani 1 1 d . . .
F1 F 0.66364(8) 1.16892(10) -0.09176(10) 0.0241(2) Uani 1 1 d . . .
F2 F 0.47612(8) 1.26709(10) -0.01837(10) 0.0250(2) Uani 1 1 d . . .
F3 F 0.47411(9) 0.99518(10) 0.35149(11) 0.0276(2) Uani 1 1 d . . .
F4 F 0.66363(8) 0.89928(10) 0.28246(10) 0.0241(2) Uani 1 1 d . . .
F5 F 0.95786(9) 0.63646(10) -0.20974(9) 0.0242(2) Uani 1 1 d . . .
F6 F 0.95051(10) 0.38452(10) -0.22796(10) 0.0303(3) Uani 1 1 d . . .
F7 F 0.75708(10) 0.36183(11) 0.16586(14) 0.0423(3) Uani 1 1 d . . .
F8 F 0.77213(9) 0.61255(10) 0.19473(11) 0.0317(3) Uani 1 1 d . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O2 1.9157(11) 3_775 ?
Cu1 O2 1.9157(11) . ?
Cu1 O1 1.9306(11) . ?
Cu1 O1 1.9306(11) 3_775 ?
O1 C7 1.273(2) . ?
O2 C9 1.2688(19) . ?
C1 F1 1.3401(19) . ?
C1 C2 1.380(2) . ?
C1 C6 1.390(2) . ?
C2 F2 1.3480(19) . ?
C2 C3 1.388(2) . ?
C3 C4 1.374(2) . ?
C3 H3 0.9500 . ?
C4 F3 1.3413(19) . ?
C4 C5 1.384(2) . ?
C5 F4 1.3461(19) . ?
C5 C6 1.389(2) . ?
C6 C7 1.512(2) . ?
C7 C8 1.386(2) . ?
C8 C9 1.395(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.501(2) . ?
C10 C11 1.393(2) . ?
C10 C15 1.396(2) . ?
C11 F5 1.3433(19) . ?
C11 C12 1.385(2) . ?
C12 F6 1.3445(19) . ?
C12 C13 1.375(3) . ?
C13 C14 1.375(3) . ?
C13 H13 0.9500 . ?
C14 F7 1.340(2) . ?
C14 C15 1.385(3) . ?
C15 F8 1.346(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 O2 180.00(6) 3_775 . ?
O2 Cu1 O1 86.87(5) 3_775 . ?
O2 Cu1 O1 93.13(5) . . ?
O2 Cu1 O1 93.13(5) 3_775 3_775 ?
O2 Cu1 O1 86.87(5) . 3_775 ?
O1 Cu1 O1 180.00(10) . 3_775 ?
C7 O1 Cu1 124.20(11) . . ?
C9 O2 Cu1 125.71(10) . . ?
F1 C1 C2 118.55(15) . . ?
F1 C1 C6 120.25(15) . . ?
C2 C1 C6 121.15(15) . . ?
F2 C2 C1 118.46(15) . . ?
F2 C2 C3 120.04(14) . . ?
C1 C2 C3 121.49(15) . . ?
C4 C3 C2 117.62(15) . . ?
C4 C3 H3 121.2 . . ?
C2 C3 H3 121.2 . . ?
F3 C4 C3 119.88(15) . . ?
F3 C4 C5 118.97(15) . . ?
C3 C4 C5 121.15(16) . . ?
F4 C5 C4 117.84(15) . . ?
F4 C5 C6 120.51(15) . . ?
C4 C5 C6 121.65(15) . . ?
C5 C6 C1 116.95(15) . . ?
C5 C6 C7 121.49(15) . . ?
C1 C6 C7 121.54(15) . . ?
O1 C7 C8 127.02(16) . . ?
O1 C7 C6 116.08(14) . . ?
C8 C7 C6 116.90(14) . . ?
C7 C8 C9 122.61(15) . . ?
C7 C8 H8 118.7 . . ?
C9 C8 H8 118.7 . . ?
O2 C9 C8 126.25(15) . . ?
O2 C9 C10 116.02(14) . . ?
C8 C9 C10 117.74(14) . . ?
C11 C10 C15 116.44(15) . . ?
C11 C10 C9 121.38(14) . . ?
C15 C10 C9 122.18(15) . . ?
F5 C11 C12 118.42(14) . . ?
F5 C11 C10 120.38(14) . . ?
C12 C11 C10 121.19(15) . . ?
F6 C12 C13 119.72(16) . . ?
F6 C12 C11 118.38(15) . . ?
C13 C12 C11 121.86(16) . . ?
C12 C13 C14 117.53(16) . . ?
C12 C13 H13 121.2 . . ?
C14 C13 H13 121.2 . . ?
F7 C14 C13 119.94(16) . . ?
F7 C14 C15 118.61(16) . . ?
C13 C14 C15 121.42(16) . . ?
F8 C15 C14 118.35(15) . . ?
F8 C15 C10 120.05(15) . . ?
C14 C15 C10 121.55(16) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 Cu1 O1 C7 -168.57(13) 3_775 . . . ?
O2 Cu1 O1 C7 11.43(13) . . . . ?
O1 Cu1 O1 C7 33(7) 3_775 . . . ?
O2 Cu1 O2 C9 47(3) 3_775 . . . ?
O1 Cu1 O2 C9 -6.99(13) . . . . ?
O1 Cu1 O2 C9 173.01(13) 3_775 . . . ?
F1 C1 C2 F2 -1.0(2) . . . . ?
C6 C1 C2 F2 -178.19(14) . . . . ?
F1 C1 C2 C3 177.61(14) . . . . ?
C6 C1 C2 C3 0.4(3) . . . . ?
F2 C2 C3 C4 178.30(15) . . . . ?
C1 C2 C3 C4 -0.3(2) . . . . ?
C2 C3 C4 F3 -179.06(15) . . . . ?
C2 C3 C4 C5 0.2(2) . . . . ?
F3 C4 C5 F4 -1.7(2) . . . . ?
C3 C4 C5 F4 179.04(15) . . . . ?
F3 C4 C5 C6 179.01(15) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
F4 C5 C6 C1 -178.92(14) . . . . ?
C4 C5 C6 C1 0.4(2) . . . . ?
F4 C5 C6 C7 2.9(2) . . . . ?
C4 C5 C6 C7 -177.83(15) . . . . ?
F1 C1 C6 C5 -177.58(14) . . . . ?
C2 C1 C6 C5 -0.5(2) . . . . ?
F1 C1 C6 C7 0.6(2) . . . . ?
C2 C1 C6 C7 177.76(15) . . . . ?
Cu1 O1 C7 C8 -11.3(2) . . . . ?
Cu1 O1 C7 C6 168.89(11) . . . . ?
C5 C6 C7 O1 -128.89(17) . . . . ?
C1 C6 C7 O1 53.0(2) . . . . ?
C5 C6 C7 C8 51.3(2) . . . . ?
C1 C6 C7 C8 -126.84(18) . . . . ?
O1 C7 C8 C9 3.0(3) . . . . ?
C6 C7 C8 C9 -177.21(15) . . . . ?
Cu1 O2 C9 C8 1.7(2) . . . . ?
Cu1 O2 C9 C10 -178.23(10) . . . . ?
C7 C8 C9 O2 2.4(3) . . . . ?
C7 C8 C9 C10 -177.66(15) . . . . ?
O2 C9 C10 C11 -45.7(2) . . . . ?
C8 C9 C10 C11 134.35(17) . . . . ?
O2 C9 C10 C15 133.55(16) . . . . ?
C8 C9 C10 C15 -46.4(2) . . . . ?
C15 C10 C11 F5 179.24(14) . . . . ?
C9 C10 C11 F5 -1.5(2) . . . . ?
C15 C10 C11 C12 0.0(2) . . . . ?
C9 C10 C11 C12 179.31(15) . . . . ?
F5 C11 C12 F6 3.7(2) . . . . ?
C10 C11 C12 F6 -177.04(14) . . . . ?
F5 C11 C12 C13 -178.53(15) . . . . ?
C10 C11 C12 C13 0.7(2) . . . . ?
F6 C12 C13 C14 177.02(16) . . . . ?
C11 C12 C13 C14 -0.7(3) . . . . ?
C12 C13 C14 F7 -178.15(16) . . . . ?
C12 C13 C14 C15 0.0(3) . . . . ?
F7 C14 C15 F8 1.5(3) . . . . ?
C13 C14 C15 F8 -176.65(17) . . . . ?
F7 C14 C15 C10 178.90(16) . . . . ?
C13 C14 C15 C10 0.7(3) . . . . ?
C11 C10 C15 F8 176.62(15) . . . . ?
C9 C10 C15 F8 -2.7(2) . . . . ?
C11 C10 C15 C14 -0.7(2) . . . . ?
C9 C10 C15 C14 179.99(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.059
_database_code_depnum_ccdc_archive 'CCDC 895485'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_100308a1
#TrackingRef 'web_deposit_cif_file_1_AkikoHori_1344479419.100308a1.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H6 Cu F16 O4, 2(C6 H6)'
_chemical_formula_sum            'C42 H18 Cu F16 O4'
_chemical_formula_weight         954.11

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   8.8327(4)
_cell_length_b                   20.6413(10)
_cell_length_c                   10.5150(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.6550(10)
_cell_angle_gamma                90.00
_cell_volume                     1836.65(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    9960
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      27.87

_exptl_crystal_description       prismatic
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.725
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             950
_exptl_absorpt_coefficient_mu    0.722
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7611
_exptl_absorpt_correction_T_max  0.8995
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            20494
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0157
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4186
_reflns_number_gt                3866
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0366P)²+1.0110P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4186
_refine_ls_number_parameters     286
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0270
_refine_ls_wR_factor_ref         0.0731
_refine_ls_wR_factor_gt          0.0716
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.0000 0.5000 0.5000 0.01560(7) Uani 1 2 d S . .
O1 O 0.04454(12) 0.48277(5) 0.33567(9) 0.0189(2) Uani 1 1 d . . .
O2 O 0.14389(11) 0.43489(5) 0.59368(9) 0.0182(2) Uani 1 1 d . . .
C1 C 0.20013(17) 0.48034(7) 0.11376(14) 0.0206(3) Uani 1 1 d . . .
C2 C 0.19561(18) 0.47645(8) -0.01861(15) 0.0231(3) Uani 1 1 d . . .
C3 C 0.12385(18) 0.42469(7) -0.09597(14) 0.0234(3) Uani 1 1 d . . .
H3 H 0.1186 0.4224 -0.1874 0.028 Uiso 1 1 calc R . .
C4 C 0.06031(19) 0.37670(7) -0.03666(14) 0.0243(3) Uani 1 1 d . . .
C5 C 0.06832(18) 0.37951(7) 0.09657(14) 0.0221(3) Uani 1 1 d . . .
C6 C 0.13724(16) 0.43186(7) 0.17431(13) 0.0186(3) Uani 1 1 d . . .
C7 C 0.13453(16) 0.43837(7) 0.31654(13) 0.0175(3) Uani 1 1 d . . .
C8 C 0.22669(17) 0.39610(7) 0.41120(14) 0.0202(3) Uani 1 1 d . . .
H8 H 0.2928 0.3658 0.3848 0.024 Uiso 1 1 calc R . .
C9 C 0.22464(16) 0.39695(7) 0.54347(13) 0.0176(3) Uani 1 1 d . . .
C10 C 0.32517(16) 0.34916(7) 0.63918(14) 0.0191(3) Uani 1 1 d . . .
C11 C 0.41716(17) 0.36911(7) 0.76461(14) 0.0210(3) Uani 1 1 d . . .
C12 C 0.50658(18) 0.32518(8) 0.85506(14) 0.0255(3) Uani 1 1 d . . .
C13 C 0.50517(18) 0.26008(8) 0.82577(15) 0.0270(3) Uani 1 1 d . . .
H13 H 0.5649 0.2300 0.8887 0.032 Uiso 1 1 calc R . .
C14 C 0.41446(18) 0.23991(7) 0.70244(16) 0.0250(3) Uani 1 1 d . . .
C15 C 0.32709(17) 0.28360(7) 0.61066(14) 0.0221(3) Uani 1 1 d . . .
C16 C 0.15206(19) 0.67780(8) 0.45517(17) 0.0301(3) Uani 1 1 d . . .
H16 H 0.0909 0.7102 0.3992 0.036 Uiso 1 1 calc R . .
C17 C 0.2489(2) 0.63764(9) 0.40763(17) 0.0313(4) Uani 1 1 d . . .
H17 H 0.2545 0.6426 0.3193 0.038 Uiso 1 1 calc R . .
C18 C 0.3379(2) 0.59015(8) 0.48913(18) 0.0323(4) Uani 1 1 d . . .
H18 H 0.4043 0.5625 0.4565 0.039 Uiso 1 1 calc R . .
C19 C 0.3299(2) 0.58312(8) 0.61806(18) 0.0332(4) Uani 1 1 d . . .
H19 H 0.3907 0.5506 0.6738 0.040 Uiso 1 1 calc R . .
C20 C 0.2332(2) 0.62356(9) 0.66579(17) 0.0323(4) Uani 1 1 d . . .
H20 H 0.2281 0.6188 0.7543 0.039 Uiso 1 1 calc R . .
C21 C 0.14395(19) 0.67090(8) 0.58439(17) 0.0304(3) Uani 1 1 d . . .
H21 H 0.0775 0.6985 0.6169 0.037 Uiso 1 1 calc R . .
F1 F 0.26675(11) 0.53240(4) 0.18525(9) 0.0284(2) Uani 1 1 d . . .
F2 F 0.25869(12) 0.52478(5) -0.07187(9) 0.0330(2) Uani 1 1 d . . .
F3 F -0.01383(13) 0.32595(5) -0.10880(9) 0.0330(2) Uani 1 1 d . . .
F4 F 0.00595(13) 0.33071(4) 0.15050(9) 0.0328(2) Uani 1 1 d . . .
F5 F 0.42328(11) 0.43186(4) 0.79786(9) 0.0269(2) Uani 1 1 d . . .
F6 F 0.59494(12) 0.34694(5) 0.97310(9) 0.0379(2) Uani 1 1 d . . .
F7 F 0.40752(12) 0.17678(5) 0.67011(11) 0.0351(2) Uani 1 1 d . . .
F8 F 0.23940(11) 0.26042(4) 0.49290(9) 0.0292(2) Uani 1 1 d . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.9123(10) . ?
Cu1 O1 1.9123(10) 3_566 ?
Cu1 O2 1.9168(9) 3_566 ?
Cu1 O2 1.9168(9) . ?
O1 C7 1.2664(17) . ?
O2 C9 1.2714(17) . ?
C1 F1 1.3463(17) . ?
C1 C2 1.383(2) . ?
C1 C6 1.385(2) . ?
C2 F2 1.3410(18) . ?
C2 C3 1.382(2) . ?
C3 C4 1.373(2) . ?
C3 H3 0.9500 . ?
C4 F3 1.3480(17) . ?
C4 C5 1.384(2) . ?
C5 F4 1.3485(17) . ?
C5 C6 1.386(2) . ?
C6 C7 1.5086(18) . ?
C7 C8 1.3965(19) . ?
C8 C9 1.3962(19) . ?
C8 H8 0.9500 . ?
C9 C10 1.5042(18) . ?
C10 C15 1.387(2) . ?
C10 C11 1.398(2) . ?
C11 F5 1.3386(17) . ?
C11 C12 1.386(2) . ?
C12 F6 1.3402(18) . ?
C12 C13 1.378(2) . ?
C13 C14 1.379(2) . ?
C13 H13 0.9500 . ?
C14 F7 1.3437(18) . ?
C14 C15 1.383(2) . ?
C15 F8 1.3462(17) . ?
C16 C17 1.383(3) . ?
C16 C21 1.388(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.388(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.385(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.388(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.386(2) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 180.00(5) . 3_566 ?
O1 Cu1 O2 86.78(4) . 3_566 ?
O1 Cu1 O2 93.22(4) 3_566 3_566 ?
O1 Cu1 O2 93.22(4) . . ?
O1 Cu1 O2 86.78(4) 3_566 . ?
O2 Cu1 O2 180.00(4) 3_566 . ?
C7 O1 Cu1 125.39(9) . . ?
C9 O2 Cu1 125.92(9) . . ?
F1 C1 C2 119.35(13) . . ?
F1 C1 C6 119.25(13) . . ?
C2 C1 C6 121.39(14) . . ?
F2 C2 C3 120.32(13) . . ?
F2 C2 C1 118.78(14) . . ?
C3 C2 C1 120.88(14) . . ?
C4 C3 C2 117.94(13) . . ?
C4 C3 H3 121.0 . . ?
C2 C3 H3 121.0 . . ?
F3 C4 C3 120.06(13) . . ?
F3 C4 C5 118.55(14) . . ?
C3 C4 C5 121.38(14) . . ?
F4 C5 C4 119.08(13) . . ?
F4 C5 C6 119.84(13) . . ?
C4 C5 C6 121.08(14) . . ?
C1 C6 C5 117.28(13) . . ?
C1 C6 C7 120.92(13) . . ?
C5 C6 C7 121.67(13) . . ?
O1 C7 C8 127.09(13) . . ?
O1 C7 C6 114.27(12) . . ?
C8 C7 C6 118.64(12) . . ?
C9 C8 C7 122.06(13) . . ?
C9 C8 H8 119.0 . . ?
C7 C8 H8 119.0 . . ?
O2 C9 C8 126.19(13) . . ?
O2 C9 C10 114.83(12) . . ?
C8 C9 C10 118.98(12) . . ?
C15 C10 C11 116.84(13) . . ?
C15 C10 C9 122.46(13) . . ?
C11 C10 C9 120.66(13) . . ?
F5 C11 C12 118.78(13) . . ?
F5 C11 C10 120.03(13) . . ?
C12 C11 C10 121.17(14) . . ?
F6 C12 C13 119.97(14) . . ?
F6 C12 C11 118.84(14) . . ?
C13 C12 C11 121.19(14) . . ?
C12 C13 C14 118.05(14) . . ?
C12 C13 H13 121.0 . . ?
C14 C13 H13 121.0 . . ?
F7 C14 C13 120.19(14) . . ?
F7 C14 C15 118.68(14) . . ?
C13 C14 C15 121.12(15) . . ?
F8 C15 C14 117.96(14) . . ?
F8 C15 C10 120.41(13) . . ?
C14 C15 C10 121.61(14) . . ?
C17 C16 C21 120.20(16) . . ?
C17 C16 H16 119.9 . . ?
C21 C16 H16 119.9 . . ?
C16 C17 C18 119.96(16) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C19 C18 C17 119.96(16) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 120.03(16) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C21 C20 C19 120.06(16) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C16 119.79(16) . . ?
C20 C21 H21 120.1 . . ?
C16 C21 H21 120.1 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 Cu1 O1 C7 159.8(15) 3_566 . . . ?
O2 Cu1 O1 C7 -176.24(11) 3_566 . . . ?
O2 Cu1 O1 C7 3.76(11) . . . . ?
O1 Cu1 O2 C9 -2.29(11) . . . . ?
O1 Cu1 O2 C9 177.71(11) 3_566 . . . ?
O2 Cu1 O2 C9 125(14) 3_566 . . . ?
F1 C1 C2 F2 0.3(2) . . . . ?
C6 C1 C2 F2 -179.85(13) . . . . ?
F1 C1 C2 C3 -178.00(13) . . . . ?
C6 C1 C2 C3 1.9(2) . . . . ?
F2 C2 C3 C4 -179.61(14) . . . . ?
C1 C2 C3 C4 -1.4(2) . . . . ?
C2 C3 C4 F3 178.59(13) . . . . ?
C2 C3 C4 C5 -0.4(2) . . . . ?
F3 C4 C5 F4 1.9(2) . . . . ?
C3 C4 C5 F4 -179.12(14) . . . . ?
F3 C4 C5 C6 -177.28(13) . . . . ?
C3 C4 C5 C6 1.7(2) . . . . ?
F1 C1 C6 C5 179.32(13) . . . . ?
C2 C1 C6 C5 -0.5(2) . . . . ?
F1 C1 C6 C7 3.4(2) . . . . ?
C2 C1 C6 C7 -176.49(13) . . . . ?
F4 C5 C6 C1 179.64(13) . . . . ?
C4 C5 C6 C1 -1.2(2) . . . . ?
F4 C5 C6 C7 -4.4(2) . . . . ?
C4 C5 C6 C7 174.69(13) . . . . ?
Cu1 O1 C7 C8 -4.5(2) . . . . ?
Cu1 O1 C7 C6 174.86(9) . . . . ?
C1 C6 C7 O1 66.78(17) . . . . ?
C5 C6 C7 O1 -108.99(15) . . . . ?
C1 C6 C7 C8 -113.83(16) . . . . ?
C5 C6 C7 C8 70.40(18) . . . . ?
O1 C7 C8 C9 2.5(2) . . . . ?
C6 C7 C8 C9 -176.81(13) . . . . ?
Cu1 O2 C9 C8 1.3(2) . . . . ?
Cu1 O2 C9 C10 -178.43(9) . . . . ?
C7 C8 C9 O2 -0.8(2) . . . . ?
C7 C8 C9 C10 178.98(13) . . . . ?
O2 C9 C10 C15 131.58(14) . . . . ?
C8 C9 C10 C15 -48.2(2) . . . . ?
O2 C9 C10 C11 -45.85(18) . . . . ?
C8 C9 C10 C11 134.38(14) . . . . ?
C15 C10 C11 F5 178.70(13) . . . . ?
C9 C10 C11 F5 -3.7(2) . . . . ?
C15 C10 C11 C12 0.5(2) . . . . ?
C9 C10 C11 C12 178.06(13) . . . . ?
F5 C11 C12 F6 0.6(2) . . . . ?
C10 C11 C12 F6 178.82(13) . . . . ?
F5 C11 C12 C13 -179.75(14) . . . . ?
C10 C11 C12 C13 -1.5(2) . . . . ?
F6 C12 C13 C14 -179.05(14) . . . . ?
C11 C12 C13 C14 1.3(2) . . . . ?
C12 C13 C14 F7 -179.00(14) . . . . ?
C12 C13 C14 C15 -0.1(2) . . . . ?
F7 C14 C15 F8 -0.1(2) . . . . ?
C13 C14 C15 F8 -179.05(13) . . . . ?
F7 C14 C15 C10 178.01(13) . . . . ?
C13 C14 C15 C10 -0.9(2) . . . . ?
C11 C10 C15 F8 178.80(13) . . . . ?
C9 C10 C15 F8 1.3(2) . . . . ?
C11 C10 C15 C14 0.7(2) . . . . ?
C9 C10 C15 C14 -176.83(13) . . . . ?
C21 C16 C17 C18 0.2(2) . . . . ?
C16 C17 C18 C19 -0.1(2) . . . . ?
C17 C18 C19 C20 -0.1(2) . . . . ?
C18 C19 C20 C21 0.2(2) . . . . ?
C19 C20 C21 C16 -0.2(2) . . . . ?
C17 C16 C21 C20 -0.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.471
_refine_diff_density_rms         0.051
_database_code_depnum_ccdc_archive 'CCDC 895486'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_110201a1
#TrackingRef 'web_deposit_cif_file_2_AkikoHori_1344479419.110201a1.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C44 H22 Cu F16 O6'
_chemical_formula_sum            'C44 H22 Cu F16 O6'
_chemical_formula_weight         1014.17

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.728(2)
_cell_length_b                   11.089(3)
_cell_length_c                   12.681(4)
_cell_angle_alpha                106.688(3)
_cell_angle_beta                 104.543(3)
_cell_angle_gamma                92.432(3)
_cell_volume                     999.9(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    100
_cell_measurement_reflns_used    6793
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      27.91

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.684
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             507
_exptl_absorpt_coefficient_mu    0.672
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8238
_exptl_absorpt_correction_T_max  0.8773
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            11323
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.74
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4461
_reflns_number_gt                4164
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0367P)²+0.3692P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4461
_refine_ls_number_parameters     305
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0269
_refine_ls_wR_factor_ref         0.0739
_refine_ls_wR_factor_gt          0.0721
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.0000 1.0000 0.0000 0.01626(7) Uani 1 2 d S . .
O1 O 0.06433(13) 0.84045(9) 0.01978(8) 0.0189(2) Uani 1 1 d . . .
O2 O 0.19335(13) 1.09698(9) 0.12930(8) 0.01866(19) Uani 1 1 d . . .
O3 O 0.19597(15) 0.98374(10) -0.14311(9) 0.0279(2) Uani 1 1 d . . .
C1 C 0.2549(2) 0.61274(14) 0.02199(13) 0.0244(3) Uani 1 1 d . . .
C2 C 0.2639(2) 0.48666(14) 0.01616(15) 0.0302(3) Uani 1 1 d . . .
C3 C 0.2141(2) 0.43842(14) 0.09383(15) 0.0342(4) Uani 1 1 d . . .
H3 H 0.2195 0.3517 0.0895 0.041 Uiso 1 1 calc R . .
C4 C 0.1562(2) 0.52039(15) 0.17832(14) 0.0338(4) Uani 1 1 d . . .
C5 C 0.1482(2) 0.64655(14) 0.18586(12) 0.0260(3) Uani 1 1 d . . .
C6 C 0.19663(18) 0.69532(12) 0.10696(12) 0.0189(3) Uani 1 1 d . . .
C7 C 0.17617(18) 0.83001(12) 0.10835(11) 0.0171(3) Uani 1 1 d . . .
C8 C 0.27841(18) 0.92711(13) 0.20283(11) 0.0188(3) Uani 1 1 d . . .
H8 H 0.3493 0.9061 0.2665 0.023 Uiso 1 1 calc R . .
C9 C 0.28071(17) 1.05500(13) 0.20756(11) 0.0177(3) Uani 1 1 d . . .
C10 C 0.39565(18) 1.15437(13) 0.31176(12) 0.0191(3) Uani 1 1 d . . .
C11 C 0.48921(19) 1.25908(13) 0.30179(13) 0.0225(3) Uani 1 1 d . . .
C12 C 0.5826(2) 1.35679(14) 0.39707(14) 0.0275(3) Uani 1 1 d . . .
C13 C 0.5866(2) 1.35533(15) 0.50610(14) 0.0311(3) Uani 1 1 d . . .
H13 H 0.6499 1.4234 0.5715 0.037 Uiso 1 1 calc R . .
C14 C 0.4961(2) 1.25213(15) 0.51700(13) 0.0271(3) Uani 1 1 d . . .
C15 C 0.40414(19) 1.15264(13) 0.42244(12) 0.0221(3) Uani 1 1 d . . .
C16 C 0.0629(2) 0.78654(14) -0.27579(13) 0.0239(3) Uani 1 1 d . . .
H16 H 0.0563 0.7577 -0.2131 0.029 Uiso 1 1 calc R . .
C17 C -0.0037(2) 0.70633(14) -0.38714(13) 0.0267(3) Uani 1 1 d . . .
H17 H -0.0581 0.6229 -0.4006 0.032 Uiso 1 1 calc R . .
C18 C 0.0086(2) 0.74713(16) -0.47940(14) 0.0297(3) Uani 1 1 d . . .
H18 H -0.0378 0.6922 -0.5556 0.036 Uiso 1 1 calc R . .
C19 C 0.0890(2) 0.86819(16) -0.45889(14) 0.0304(3) Uani 1 1 d . . .
H19 H 0.0999 0.8956 -0.5216 0.037 Uiso 1 1 calc R . .
C20 C 0.1542(2) 0.95079(15) -0.34804(14) 0.0279(3) Uani 1 1 d . . .
H20 H 0.2081 1.0343 -0.3350 0.033 Uiso 1 1 calc R . .
C21 C 0.1394(2) 0.90951(14) -0.25644(13) 0.0234(3) Uani 1 1 d . . .
C22 C 0.2887(2) 1.10709(16) -0.11892(16) 0.0371(4) Uani 1 1 d . . .
H22A H 0.3946 1.0992 -0.1486 0.056 Uiso 1 1 calc R . .
H22B H 0.3271 1.1486 -0.0359 0.056 Uiso 1 1 calc R . .
H22C H 0.2079 1.1580 -0.1557 0.056 Uiso 1 1 calc R . .
F1 F 0.30489(14) 0.65495(9) -0.05628(9) 0.0351(2) Uani 1 1 d . . .
F2 F 0.32100(15) 0.41075(9) -0.06888(10) 0.0460(3) Uani 1 1 d . . .
F3 F 0.10307(19) 0.47740(10) 0.25594(9) 0.0563(4) Uani 1 1 d . . .
F4 F 0.08768(15) 0.72155(9) 0.26912(8) 0.0381(2) Uani 1 1 d . . .
F5 F 0.49392(12) 1.26541(8) 0.19866(8) 0.02758(19) Uani 1 1 d . . .
F6 F 0.67072(14) 1.45553(9) 0.38270(9) 0.0381(2) Uani 1 1 d . . .
F7 F 0.49514(14) 1.24659(10) 0.62170(8) 0.0370(2) Uani 1 1 d . . .
F8 F 0.31824(12) 1.05558(8) 0.43988(7) 0.02727(19) Uani 1 1 d . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O2 1.9231(10) . ?
Cu1 O2 1.9231(10) 2_575 ?
Cu1 O1 1.9255(10) . ?
Cu1 O1 1.9255(10) 2_575 ?
Cu1 O3 2.6144(12) . ?
O1 C7 1.2717(16) . ?
O2 C9 1.2699(16) . ?
O3 C21 1.3815(18) . ?
O3 C22 1.4297(19) . ?
C1 F1 1.3406(18) . ?
C1 C6 1.384(2) . ?
C1 C2 1.384(2) . ?
C2 F2 1.347(2) . ?
C2 C3 1.371(3) . ?
C3 C4 1.375(3) . ?
C3 H3 0.9500 . ?
C4 F3 1.3492(19) . ?
C4 C5 1.380(2) . ?
C5 F4 1.3425(19) . ?
C5 C6 1.384(2) . ?
C6 C7 1.5042(18) . ?
C7 C8 1.3895(19) . ?
C8 C9 1.4014(19) . ?
C8 H8 0.9500 . ?
C9 C10 1.4968(19) . ?
C10 C15 1.394(2) . ?
C10 C11 1.395(2) . ?
C11 F5 1.3391(17) . ?
C11 C12 1.378(2) . ?
C12 F6 1.3453(18) . ?
C12 C13 1.380(2) . ?
C13 C14 1.374(2) . ?
C13 H13 0.9500 . ?
C14 F7 1.3485(18) . ?
C14 C15 1.381(2) . ?
C15 F8 1.3408(17) . ?
C16 C17 1.387(2) . ?
C16 C21 1.391(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.392(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.380(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.391(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.393(2) . ?
C20 H20 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 O2 179.999(1) . 2_575 ?
O2 Cu1 O1 93.13(4) . . ?
O2 Cu1 O1 86.87(4) 2_575 . ?
O2 Cu1 O1 86.87(4) . 2_575 ?
O2 Cu1 O1 93.13(4) 2_575 2_575 ?
O1 Cu1 O1 180.0 . 2_575 ?
O2 Cu1 O3 92.98(4) . . ?
O2 Cu1 O3 87.02(4) 2_575 . ?
O1 Cu1 O3 90.50(4) . . ?
O1 Cu1 O3 89.50(4) 2_575 . ?
C7 O1 Cu1 123.96(9) . . ?
C9 O2 Cu1 124.88(9) . . ?
C21 O3 C22 117.12(12) . . ?
C21 O3 Cu1 123.40(9) . . ?
C22 O3 Cu1 107.72(9) . . ?
F1 C1 C6 119.78(13) . . ?
F1 C1 C2 118.89(14) . . ?
C6 C1 C2 121.33(14) . . ?
F2 C2 C3 120.09(14) . . ?
F2 C2 C1 118.58(15) . . ?
C3 C2 C1 121.33(15) . . ?
C2 C3 C4 117.40(14) . . ?
C2 C3 H3 121.3 . . ?
C4 C3 H3 121.3 . . ?
F3 C4 C3 119.82(15) . . ?
F3 C4 C5 118.27(16) . . ?
C3 C4 C5 121.90(15) . . ?
F4 C5 C4 119.20(14) . . ?
F4 C5 C6 119.89(13) . . ?
C4 C5 C6 120.88(15) . . ?
C1 C6 C5 117.16(13) . . ?
C1 C6 C7 120.96(12) . . ?
C5 C6 C7 121.77(13) . . ?
O1 C7 C8 127.60(12) . . ?
O1 C7 C6 114.25(11) . . ?
C8 C7 C6 118.16(12) . . ?
C7 C8 C9 122.31(12) . . ?
C7 C8 H8 118.8 . . ?
C9 C8 H8 118.8 . . ?
O2 C9 C8 125.75(12) . . ?
O2 C9 C10 114.93(12) . . ?
C8 C9 C10 119.32(12) . . ?
C15 C10 C11 116.78(13) . . ?
C15 C10 C9 122.38(13) . . ?
C11 C10 C9 120.67(12) . . ?
F5 C11 C12 118.24(13) . . ?
F5 C11 C10 120.44(13) . . ?
C12 C11 C10 121.30(14) . . ?
F6 C12 C11 118.91(14) . . ?
F6 C12 C13 119.72(14) . . ?
C11 C12 C13 121.37(14) . . ?
C14 C13 C12 117.83(14) . . ?
C14 C13 H13 121.1 . . ?
C12 C13 H13 121.1 . . ?
F7 C14 C13 120.08(14) . . ?
F7 C14 C15 118.44(14) . . ?
C13 C14 C15 121.47(15) . . ?
F8 C15 C14 118.03(13) . . ?
F8 C15 C10 120.73(13) . . ?
C14 C15 C10 121.21(14) . . ?
C17 C16 C21 119.64(13) . . ?
C17 C16 H16 120.2 . . ?
C21 C16 H16 120.2 . . ?
C16 C17 C18 120.53(14) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C19 C18 C17 119.24(15) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C18 C19 C20 121.17(14) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C19 C20 C21 119.12(14) . . ?
C19 C20 H20 120.4 . . ?
C21 C20 H20 120.4 . . ?
O3 C21 C16 115.47(13) . . ?
O3 C21 C20 124.26(13) . . ?
C16 C21 C20 120.27(14) . . ?
O3 C22 H22A 109.5 . . ?
O3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 Cu1 O1 C7 11.98(11) . . . . ?
O2 Cu1 O1 C7 -168.02(11) 2_575 . . . ?
O1 Cu1 O1 C7 -41(46) 2_575 . . . ?
O3 Cu1 O1 C7 104.99(11) . . . . ?
O2 Cu1 O2 C9 -135(29) 2_575 . . . ?
O1 Cu1 O2 C9 -16.92(11) . . . . ?
O1 Cu1 O2 C9 163.08(11) 2_575 . . . ?
O3 Cu1 O2 C9 -107.58(10) . . . . ?
O2 Cu1 O3 C21 172.48(10) . . . . ?
O2 Cu1 O3 C21 -7.53(10) 2_575 . . . ?
O1 Cu1 O3 C21 79.31(10) . . . . ?
O1 Cu1 O3 C21 -100.69(10) 2_575 . . . ?
O2 Cu1 O3 C22 -45.91(11) . . . . ?
O2 Cu1 O3 C22 134.09(11) 2_575 . . . ?
O1 Cu1 O3 C22 -139.07(11) . . . . ?
O1 Cu1 O3 C22 40.93(11) 2_575 . . . ?
F1 C1 C2 F2 -0.7(2) . . . . ?
C6 C1 C2 F2 179.71(13) . . . . ?
F1 C1 C2 C3 -179.87(14) . . . . ?
C6 C1 C2 C3 0.5(2) . . . . ?
F2 C2 C3 C4 -179.68(14) . . . . ?
C1 C2 C3 C4 -0.5(2) . . . . ?
C2 C3 C4 F3 179.01(15) . . . . ?
C2 C3 C4 C5 -0.2(2) . . . . ?
F3 C4 C5 F4 -0.3(2) . . . . ?
C3 C4 C5 F4 178.90(14) . . . . ?
F3 C4 C5 C6 -178.36(14) . . . . ?
C3 C4 C5 C6 0.8(2) . . . . ?
F1 C1 C6 C5 -179.47(13) . . . . ?
C2 C1 C6 C5 0.1(2) . . . . ?
F1 C1 C6 C7 4.3(2) . . . . ?
C2 C1 C6 C7 -176.12(13) . . . . ?
F4 C5 C6 C1 -178.85(13) . . . . ?
C4 C5 C6 C1 -0.8(2) . . . . ?
F4 C5 C6 C7 -2.6(2) . . . . ?
C4 C5 C6 C7 175.44(14) . . . . ?
Cu1 O1 C7 C8 -3.58(19) . . . . ?
Cu1 O1 C7 C6 176.70(8) . . . . ?
C1 C6 C7 O1 60.16(17) . . . . ?
C5 C6 C7 O1 -115.92(15) . . . . ?
C1 C6 C7 C8 -119.60(15) . . . . ?
C5 C6 C7 C8 64.32(18) . . . . ?
O1 C7 C8 C9 -5.5(2) . . . . ?
C6 C7 C8 C9 174.22(12) . . . . ?
Cu1 O2 C9 C8 13.68(19) . . . . ?
Cu1 O2 C9 C10 -166.97(8) . . . . ?
C7 C8 C9 O2 -0.1(2) . . . . ?
C7 C8 C9 C10 -179.38(12) . . . . ?
O2 C9 C10 C15 136.71(13) . . . . ?
C8 C9 C10 C15 -43.90(19) . . . . ?
O2 C9 C10 C11 -38.32(18) . . . . ?
C8 C9 C10 C11 141.08(14) . . . . ?
C15 C10 C11 F5 177.23(12) . . . . ?
C9 C10 C11 F5 -7.5(2) . . . . ?
C15 C10 C11 C12 -1.1(2) . . . . ?
C9 C10 C11 C12 174.18(13) . . . . ?
F5 C11 C12 F6 1.5(2) . . . . ?
C10 C11 C12 F6 179.93(13) . . . . ?
F5 C11 C12 C13 -178.70(13) . . . . ?
C10 C11 C12 C13 -0.3(2) . . . . ?
F6 C12 C13 C14 -179.42(14) . . . . ?
C11 C12 C13 C14 0.8(2) . . . . ?
C12 C13 C14 F7 -179.60(14) . . . . ?
C12 C13 C14 C15 0.1(2) . . . . ?
F7 C14 C15 F8 0.1(2) . . . . ?
C13 C14 C15 F8 -179.63(13) . . . . ?
F7 C14 C15 C10 178.12(12) . . . . ?
C13 C14 C15 C10 -1.6(2) . . . . ?
C11 C10 C15 F8 -179.97(12) . . . . ?
C9 C10 C15 F8 4.8(2) . . . . ?
C11 C10 C15 C14 2.1(2) . . . . ?
C9 C10 C15 C14 -173.16(13) . . . . ?
C21 C16 C17 C18 1.2(2) . . . . ?
C16 C17 C18 C19 0.4(2) . . . . ?
C17 C18 C19 C20 -1.4(2) . . . . ?
C18 C19 C20 C21 0.7(2) . . . . ?
C22 O3 C21 C16 174.99(14) . . . . ?
Cu1 O3 C21 C16 -46.66(16) . . . . ?
C22 O3 C21 C20 -5.3(2) . . . . ?
Cu1 O3 C21 C20 133.01(12) . . . . ?
C17 C16 C21 O3 177.75(13) . . . . ?
C17 C16 C21 C20 -1.9(2) . . . . ?
C19 C20 C21 O3 -178.66(14) . . . . ?
C19 C20 C21 C16 1.0(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.049
_database_code_depnum_ccdc_archive 'CCDC 895487'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_110418b1
#TrackingRef 'web_deposit_cif_file_3_AkikoHori_1344479419.110418b1.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H6 Cu F16 O4, C8 H10'
_chemical_formula_sum            'C38 H16 Cu F16 O4'
_chemical_formula_weight         904.06

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   29.351(3)
_cell_length_b                   10.5754(12)
_cell_length_c                   21.985(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.8570(10)
_cell_angle_gamma                90.00
_cell_volume                     6775.3(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    100
_cell_measurement_reflns_used    5617
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      27.69

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.773
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3592
_exptl_absorpt_coefficient_mu    0.777
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8923
_exptl_absorpt_correction_T_max  0.9771
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            37362
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_av_sigmaI/netI    0.0490
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         27.48
_reflns_number_total             7736
_reflns_number_gt                5257
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0364P)²+5.6536P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7736
_refine_ls_number_parameters     534
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.0901
_refine_ls_wR_factor_gt          0.0765
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.041596(9) 0.74518(3) 0.410526(12) 0.01463(8) Uani 1 1 d . . .
O1 O 0.03156(5) 0.91948(14) 0.38921(7) 0.0161(3) Uani 1 1 d . . .
O2 O -0.01526(5) 0.69142(14) 0.36581(7) 0.0171(4) Uani 1 1 d . . .
O3 O 0.05427(5) 0.57041(14) 0.42588(7) 0.0167(4) Uani 1 1 d . . .
O4 O 0.09689(5) 0.79913(14) 0.45837(7) 0.0178(4) Uani 1 1 d . . .
C1 C 0.03113(9) 1.1675(2) 0.32336(11) 0.0199(5) Uani 1 1 d . . .
C2 C 0.03158(9) 1.2978(2) 0.31947(11) 0.0244(6) Uani 1 1 d . . .
C3 C -0.00212(9) 1.3699(2) 0.34086(12) 0.0281(6) Uani 1 1 d . . .
H3 H -0.0016 1.4595 0.3382 0.034 Uiso 1 1 calc R . .
C4 C -0.03663(9) 1.3086(2) 0.36612(13) 0.0267(6) Uani 1 1 d . . .
C5 C -0.03743(9) 1.1783(2) 0.37015(12) 0.0232(6) Uani 1 1 d . . .
C6 C -0.00374(8) 1.1047(2) 0.34864(11) 0.0174(5) Uani 1 1 d . . .
C7 C -0.00315(8) 0.9629(2) 0.35568(10) 0.0161(5) Uani 1 1 d . . .
C8 C -0.03975(8) 0.8932(2) 0.32663(11) 0.0191(5) Uani 1 1 d . . .
H8 H -0.0630 0.9362 0.3009 0.023 Uiso 1 1 calc R . .
C9 C -0.04354(8) 0.7634(2) 0.33375(10) 0.0153(5) Uani 1 1 d . . .
C10 C -0.08573(8) 0.6974(2) 0.30297(10) 0.0149(5) Uani 1 1 d . . .
C11 C -0.11674(8) 0.6392(2) 0.33640(10) 0.0176(5) Uani 1 1 d . . .
C12 C -0.15540(8) 0.5802(2) 0.30878(11) 0.0195(5) Uani 1 1 d . . .
C13 C -0.16458(8) 0.5749(2) 0.24602(11) 0.0209(5) Uani 1 1 d . . .
H13 H -0.1912 0.5336 0.2269 0.025 Uiso 1 1 calc R . .
C14 C -0.13402(8) 0.6313(2) 0.21190(10) 0.0208(5) Uani 1 1 d . . .
C15 C -0.09561(8) 0.6929(2) 0.23962(11) 0.0188(5) Uani 1 1 d . . .
C16 C 0.05505(8) 0.3145(2) 0.48137(10) 0.0169(5) Uani 1 1 d . . .
C17 C 0.05679(8) 0.1844(2) 0.48491(11) 0.0189(5) Uani 1 1 d . . .
C18 C 0.09362(8) 0.1175(2) 0.46886(11) 0.0209(6) Uani 1 1 d . . .
H18 H 0.0946 0.0279 0.4713 0.025 Uiso 1 1 calc R . .
C19 C 0.12899(8) 0.1853(2) 0.44905(11) 0.0209(6) Uani 1 1 d . . .
C20 C 0.12813(8) 0.3160(2) 0.44642(11) 0.0192(5) Uani 1 1 d . . .
C21 C 0.09090(8) 0.3840(2) 0.46241(10) 0.0146(5) Uani 1 1 d . . .
C22 C 0.08905(8) 0.5258(2) 0.45904(10) 0.0150(5) Uani 1 1 d . . .
C23 C 0.12443(8) 0.5955(2) 0.49091(10) 0.0167(5) Uani 1 1 d . . .
H23 H 0.1478 0.5520 0.5164 0.020 Uiso 1 1 calc R . .
C24 C 0.12682(8) 0.7262(2) 0.48675(10) 0.0165(5) Uani 1 1 d . . .
C25 C 0.17024(8) 0.7908(2) 0.51422(11) 0.0192(5) Uani 1 1 d . . .
C26 C 0.19607(8) 0.8581(2) 0.47613(11) 0.0215(5) Uani 1 1 d . . .
C27 C 0.23700(8) 0.9141(2) 0.49870(12) 0.0246(6) Uani 1 1 d . . .
C28 C 0.25387(8) 0.9046(2) 0.55979(13) 0.0255(6) Uani 1 1 d . . .
H28 H 0.2821 0.9433 0.5753 0.031 Uiso 1 1 calc R . .
C29 C 0.22870(9) 0.8376(2) 0.59733(12) 0.0245(6) Uani 1 1 d . . .
C30 C 0.18746(8) 0.7812(2) 0.57528(11) 0.0205(5) Uani 1 1 d . . .
C31 C 0.18815(10) 0.9644(3) 0.23627(13) 0.0333(7) Uani 1 1 d . . .
C32 C 0.16174(9) 0.9772(3) 0.18005(13) 0.0314(7) Uani 1 1 d . . .
H32 H 0.1358 1.0316 0.1767 0.038 Uiso 1 1 calc R . .
C33 C 0.17200(9) 0.9136(3) 0.12925(13) 0.0318(7) Uani 1 1 d . . .
H33 H 0.1526 0.9233 0.0917 0.038 Uiso 1 1 calc R . .
C34 C 0.21025(9) 0.8349(3) 0.13136(13) 0.0305(6) Uani 1 1 d . . .
C35 C 0.23712(10) 0.8232(3) 0.18753(15) 0.0366(7) Uani 1 1 d . . .
H35 H 0.2636 0.7709 0.1907 0.044 Uiso 1 1 calc R . .
C36 C 0.22603(10) 0.8863(3) 0.23874(14) 0.0367(7) Uani 1 1 d . . .
H36 H 0.2449 0.8756 0.2766 0.044 Uiso 1 1 calc R . .
C37 C 0.17567(12) 1.0320(3) 0.29245(14) 0.0494(9) Uani 1 1 d . . .
H37A H 0.1656 1.1182 0.2814 0.074 Uiso 1 1 calc R . .
H37B H 0.2025 1.0353 0.3235 0.074 Uiso 1 1 calc R . .
H37C H 0.1508 0.9864 0.3089 0.074 Uiso 1 1 calc R . .
C38 C 0.22181(11) 0.7659(3) 0.07513(15) 0.0442(8) Uani 1 1 d . . .
H38A H 0.2512 0.7222 0.0846 0.066 Uiso 1 1 calc R . .
H38B H 0.2240 0.8267 0.0420 0.066 Uiso 1 1 calc R . .
H38C H 0.1977 0.7040 0.0623 0.066 Uiso 1 1 calc R . .
F1 F 0.06449(5) 1.10080(13) 0.30142(7) 0.0290(4) Uani 1 1 d . . .
F2 F 0.06637(6) 1.35443(14) 0.29489(7) 0.0364(4) Uani 1 1 d . . .
F3 F -0.06967(5) 1.37561(14) 0.38847(8) 0.0415(4) Uani 1 1 d . . .
F4 F -0.07083(5) 1.12326(13) 0.39748(7) 0.0313(4) Uani 1 1 d . . .
F5 F -0.10950(5) 0.64381(13) 0.39824(6) 0.0248(3) Uani 1 1 d . . .
F6 F -0.18505(5) 0.52930(14) 0.34394(6) 0.0282(3) Uani 1 1 d . . .
F7 F -0.14124(5) 0.62813(15) 0.15021(6) 0.0335(4) Uani 1 1 d . . .
F8 F -0.06661(5) 0.74790(15) 0.20435(6) 0.0302(4) Uani 1 1 d . . .
F9 F 0.01823(4) 0.37422(13) 0.49805(6) 0.0224(3) Uani 1 1 d . . .
F10 F 0.02108(5) 0.12321(13) 0.50470(7) 0.0279(4) Uani 1 1 d . . .
F11 F 0.16587(5) 0.12555(13) 0.43196(8) 0.0339(4) Uani 1 1 d . . .
F12 F 0.16377(5) 0.37676(13) 0.42628(7) 0.0286(4) Uani 1 1 d . . .
F13 F 0.18243(5) 0.86387(13) 0.41568(6) 0.0271(3) Uani 1 1 d . . .
F14 F 0.26124(5) 0.97594(14) 0.45965(7) 0.0332(4) Uani 1 1 d . . .
F15 F 0.24400(5) 0.82660(14) 0.65757(7) 0.0336(4) Uani 1 1 d . . .
F16 F 0.16388(5) 0.71929(13) 0.61438(6) 0.0279(4) Uani 1 1 d . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O3 1.9074(16) . ?
Cu1 O4 1.9127(16) . ?
Cu1 O1 1.9160(16) . ?
Cu1 O2 1.9190(16) . ?
O1 C7 1.270(3) . ?
O2 C9 1.275(3) . ?
O3 C22 1.272(3) . ?
O4 C24 1.274(3) . ?
C1 F1 1.342(3) . ?
C1 C2 1.381(3) . ?
C1 C6 1.390(3) . ?
C2 F2 1.351(3) . ?
C2 C3 1.375(4) . ?
C3 C4 1.374(4) . ?
C3 H3 0.9500 . ?
C4 F3 1.341(3) . ?
C4 C5 1.381(3) . ?
C5 F4 1.342(3) . ?
C5 C6 1.385(3) . ?
C6 C7 1.507(3) . ?
C7 C8 1.394(3) . ?
C8 C9 1.388(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.509(3) . ?
C10 C11 1.381(3) . ?
C10 C15 1.389(3) . ?
C11 F5 1.352(3) . ?
C11 C12 1.371(3) . ?
C12 F6 1.344(3) . ?
C12 C13 1.375(3) . ?
C13 C14 1.372(3) . ?
C13 H13 0.9500 . ?
C14 F7 1.348(3) . ?
C14 C15 1.380(3) . ?
C15 F8 1.350(3) . ?
C16 F9 1.340(3) . ?
C16 C17 1.379(3) . ?
C16 C21 1.388(3) . ?
C17 F10 1.347(3) . ?
C17 C18 1.372(3) . ?
C18 C19 1.374(3) . ?
C18 H18 0.9500 . ?
C19 F11 1.345(3) . ?
C19 C20 1.383(3) . ?
C20 F12 1.347(3) . ?
C20 C21 1.388(3) . ?
C21 C22 1.502(3) . ?
C22 C23 1.392(3) . ?
C23 C24 1.388(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.507(3) . ?
C25 C30 1.381(3) . ?
C25 C26 1.391(3) . ?
C26 F13 1.343(3) . ?
C26 C27 1.378(3) . ?
C27 F14 1.348(3) . ?
C27 C28 1.378(4) . ?
C28 C29 1.369(4) . ?
C28 H28 0.9500 . ?
C29 F15 1.352(3) . ?
C29 C30 1.384(3) . ?
C30 F16 1.337(3) . ?
C31 C36 1.381(4) . ?
C31 C32 1.385(4) . ?
C31 C37 1.509(4) . ?
C32 C33 1.368(4) . ?
C32 H32 0.9500 . ?
C33 C34 1.394(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.389(4) . ?
C34 C38 1.509(4) . ?
C35 C36 1.380(4) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Cu1 O4 93.27(7) . . ?
O3 Cu1 O1 175.21(7) . . ?
O4 Cu1 O1 86.74(7) . . ?
O3 Cu1 O2 86.72(7) . . ?
O4 Cu1 O2 177.40(7) . . ?
O1 Cu1 O2 93.48(7) . . ?
C7 O1 Cu1 125.39(15) . . ?
C9 O2 Cu1 125.14(15) . . ?
C22 O3 Cu1 125.92(14) . . ?
C24 O4 Cu1 125.37(15) . . ?
F1 C1 C2 119.3(2) . . ?
F1 C1 C6 119.7(2) . . ?
C2 C1 C6 121.0(2) . . ?
F2 C2 C3 120.0(2) . . ?
F2 C2 C1 118.7(2) . . ?
C3 C2 C1 121.3(2) . . ?
C4 C3 C2 118.1(2) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
F3 C4 C3 119.9(2) . . ?
F3 C4 C5 119.0(3) . . ?
C3 C4 C5 121.0(3) . . ?
F4 C5 C4 118.7(2) . . ?
F4 C5 C6 119.9(2) . . ?
C4 C5 C6 121.3(2) . . ?
C5 C6 C1 117.2(2) . . ?
C5 C6 C7 121.6(2) . . ?
C1 C6 C7 121.1(2) . . ?
O1 C7 C8 126.6(2) . . ?
O1 C7 C6 114.7(2) . . ?
C8 C7 C6 118.7(2) . . ?
C9 C8 C7 122.7(2) . . ?
C9 C8 H8 118.7 . . ?
C7 C8 H8 118.7 . . ?
O2 C9 C8 126.7(2) . . ?
O2 C9 C10 114.7(2) . . ?
C8 C9 C10 118.6(2) . . ?
C11 C10 C15 116.5(2) . . ?
C11 C10 C9 121.7(2) . . ?
C15 C10 C9 121.8(2) . . ?
F5 C11 C12 118.9(2) . . ?
F5 C11 C10 119.0(2) . . ?
C12 C11 C10 122.0(2) . . ?
F6 C12 C11 119.1(2) . . ?
F6 C12 C13 119.9(2) . . ?
C11 C12 C13 121.0(2) . . ?
C14 C13 C12 117.9(2) . . ?
C14 C13 H13 121.0 . . ?
C12 C13 H13 121.0 . . ?
F7 C14 C13 120.3(2) . . ?
F7 C14 C15 118.6(2) . . ?
C13 C14 C15 121.1(2) . . ?
F8 C15 C14 119.2(2) . . ?
F8 C15 C10 119.4(2) . . ?
C14 C15 C10 121.4(2) . . ?
F9 C16 C17 118.7(2) . . ?
F9 C16 C21 119.9(2) . . ?
C17 C16 C21 121.4(2) . . ?
F10 C17 C18 120.2(2) . . ?
F10 C17 C16 118.2(2) . . ?
C18 C17 C16 121.6(2) . . ?
C17 C18 C19 117.4(2) . . ?
C17 C18 H18 121.3 . . ?
C19 C18 H18 121.3 . . ?
F11 C19 C18 120.5(2) . . ?
F11 C19 C20 118.0(2) . . ?
C18 C19 C20 121.6(2) . . ?
F12 C20 C19 118.7(2) . . ?
F12 C20 C21 120.1(2) . . ?
C19 C20 C21 121.2(2) . . ?
C16 C21 C20 116.7(2) . . ?
C16 C21 C22 121.3(2) . . ?
C20 C21 C22 122.0(2) . . ?
O3 C22 C23 126.3(2) . . ?
O3 C22 C21 114.84(19) . . ?
C23 C22 C21 118.9(2) . . ?
C24 C23 C22 122.3(2) . . ?
C24 C23 H23 118.8 . . ?
C22 C23 H23 118.8 . . ?
O4 C24 C23 126.7(2) . . ?
O4 C24 C25 115.00(19) . . ?
C23 C24 C25 118.2(2) . . ?
C30 C25 C26 117.4(2) . . ?
C30 C25 C24 123.4(2) . . ?
C26 C25 C24 119.1(2) . . ?
F13 C26 C27 118.8(2) . . ?
F13 C26 C25 120.0(2) . . ?
C27 C26 C25 121.2(2) . . ?
F14 C27 C26 118.9(2) . . ?
F14 C27 C28 120.0(2) . . ?
C26 C27 C28 121.1(2) . . ?
C29 C28 C27 117.9(2) . . ?
C29 C28 H28 121.0 . . ?
C27 C28 H28 121.0 . . ?
F15 C29 C28 119.7(2) . . ?
F15 C29 C30 118.7(2) . . ?
C28 C29 C30 121.6(2) . . ?
F16 C30 C25 120.2(2) . . ?
F16 C30 C29 118.9(2) . . ?
C25 C30 C29 120.8(2) . . ?
C36 C31 C32 117.1(3) . . ?
C36 C31 C37 121.6(3) . . ?
C32 C31 C37 121.3(3) . . ?
C33 C32 C31 121.8(3) . . ?
C33 C32 H32 119.1 . . ?
C31 C32 H32 119.1 . . ?
C32 C33 C34 121.4(3) . . ?
C32 C33 H33 119.3 . . ?
C34 C33 H33 119.3 . . ?
C35 C34 C33 116.9(3) . . ?
C35 C34 C38 121.7(3) . . ?
C33 C34 C38 121.4(3) . . ?
C36 C35 C34 121.2(3) . . ?
C36 C35 H35 119.4 . . ?
C34 C35 H35 119.4 . . ?
C35 C36 C31 121.6(3) . . ?
C35 C36 H36 119.2 . . ?
C31 C36 H36 119.2 . . ?
C31 C37 H37A 109.5 . . ?
C31 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C31 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C34 C38 H38A 109.5 . . ?
C34 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C34 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 Cu1 O1 C7 91.6(8) . . . . ?
O4 Cu1 O1 C7 -178.12(18) . . . . ?
O2 Cu1 O1 C7 -0.72(18) . . . . ?
O3 Cu1 O2 C9 -172.44(18) . . . . ?
O4 Cu1 O2 C9 97.7(14) . . . . ?
O1 Cu1 O2 C9 2.77(18) . . . . ?
O4 Cu1 O3 C22 1.29(18) . . . . ?
O1 Cu1 O3 C22 91.3(8) . . . . ?
O2 Cu1 O3 C22 -176.10(18) . . . . ?
O3 Cu1 O4 C24 -0.09(19) . . . . ?
O1 Cu1 O4 C24 -175.30(19) . . . . ?
O2 Cu1 O4 C24 89.7(15) . . . . ?
F1 C1 C2 F2 -1.6(3) . . . . ?
C6 C1 C2 F2 179.6(2) . . . . ?
F1 C1 C2 C3 179.4(2) . . . . ?
C6 C1 C2 C3 0.6(4) . . . . ?
F2 C2 C3 C4 -179.3(2) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C2 C3 C4 F3 178.8(2) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
F3 C4 C5 F4 -1.3(4) . . . . ?
C3 C4 C5 F4 177.3(2) . . . . ?
F3 C4 C5 C6 -179.0(2) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
F4 C5 C6 C1 -177.1(2) . . . . ?
C4 C5 C6 C1 0.6(4) . . . . ?
F4 C5 C6 C7 -0.7(4) . . . . ?
C4 C5 C6 C7 177.0(2) . . . . ?
F1 C1 C6 C5 -179.5(2) . . . . ?
C2 C1 C6 C5 -0.7(4) . . . . ?
F1 C1 C6 C7 4.1(3) . . . . ?
C2 C1 C6 C7 -177.1(2) . . . . ?
Cu1 O1 C7 C8 -1.9(3) . . . . ?
Cu1 O1 C7 C6 177.06(15) . . . . ?
C5 C6 C7 O1 -116.2(3) . . . . ?
C1 C6 C7 O1 60.0(3) . . . . ?
C5 C6 C7 C8 62.9(3) . . . . ?
C1 C6 C7 C8 -120.9(3) . . . . ?
O1 C7 C8 C9 3.2(4) . . . . ?
C6 C7 C8 C9 -175.7(2) . . . . ?
Cu1 O2 C9 C8 -2.4(3) . . . . ?
Cu1 O2 C9 C10 179.85(14) . . . . ?
C7 C8 C9 O2 -0.8(4) . . . . ?
C7 C8 C9 C10 176.9(2) . . . . ?
O2 C9 C10 C11 62.9(3) . . . . ?
C8 C9 C10 C11 -115.0(3) . . . . ?
O2 C9 C10 C15 -117.6(2) . . . . ?
C8 C9 C10 C15 64.4(3) . . . . ?
C15 C10 C11 F5 -178.1(2) . . . . ?
C9 C10 C11 F5 1.3(3) . . . . ?
C15 C10 C11 C12 -0.1(3) . . . . ?
C9 C10 C11 C12 179.3(2) . . . . ?
F5 C11 C12 F6 0.3(3) . . . . ?
C10 C11 C12 F6 -177.7(2) . . . . ?
F5 C11 C12 C13 179.0(2) . . . . ?
C10 C11 C12 C13 1.0(4) . . . . ?
F6 C12 C13 C14 178.2(2) . . . . ?
C11 C12 C13 C14 -0.4(4) . . . . ?
C12 C13 C14 F7 179.6(2) . . . . ?
C12 C13 C14 C15 -0.9(4) . . . . ?
F7 C14 C15 F8 0.0(4) . . . . ?
C13 C14 C15 F8 -179.5(2) . . . . ?
F7 C14 C15 C10 -178.7(2) . . . . ?
C13 C14 C15 C10 1.8(4) . . . . ?
C11 C10 C15 F8 -179.9(2) . . . . ?
C9 C10 C15 F8 0.6(3) . . . . ?
C11 C10 C15 C14 -1.2(4) . . . . ?
C9 C10 C15 C14 179.3(2) . . . . ?
F9 C16 C17 F10 0.4(3) . . . . ?
C21 C16 C17 F10 178.9(2) . . . . ?
F9 C16 C17 C18 -179.6(2) . . . . ?
C21 C16 C17 C18 -1.2(4) . . . . ?
F10 C17 C18 C19 -180.0(2) . . . . ?
C16 C17 C18 C19 0.1(4) . . . . ?
C17 C18 C19 F11 -179.2(2) . . . . ?
C17 C18 C19 C20 1.2(4) . . . . ?
F11 C19 C20 F12 0.8(4) . . . . ?
C18 C19 C20 F12 -179.7(2) . . . . ?
F11 C19 C20 C21 179.0(2) . . . . ?
C18 C19 C20 C21 -1.5(4) . . . . ?
F9 C16 C21 C20 179.4(2) . . . . ?
C17 C16 C21 C20 0.9(3) . . . . ?
F9 C16 C21 C22 -1.1(3) . . . . ?
C17 C16 C21 C22 -179.6(2) . . . . ?
F12 C20 C21 C16 178.5(2) . . . . ?
C19 C20 C21 C16 0.4(4) . . . . ?
F12 C20 C21 C22 -1.0(3) . . . . ?
C19 C20 C21 C22 -179.2(2) . . . . ?
Cu1 O3 C22 C23 0.5(3) . . . . ?
Cu1 O3 C22 C21 -178.98(14) . . . . ?
C16 C21 C22 O3 -55.9(3) . . . . ?
C20 C21 C22 O3 123.7(2) . . . . ?
C16 C21 C22 C23 124.6(2) . . . . ?
C20 C21 C22 C23 -55.9(3) . . . . ?
O3 C22 C23 C24 -4.0(4) . . . . ?
C21 C22 C23 C24 175.5(2) . . . . ?
Cu1 O4 C24 C23 -3.1(3) . . . . ?
Cu1 O4 C24 C25 172.26(15) . . . . ?
C22 C23 C24 O4 5.4(4) . . . . ?
C22 C23 C24 C25 -169.8(2) . . . . ?
O4 C24 C25 C30 125.5(2) . . . . ?
C23 C24 C25 C30 -58.8(3) . . . . ?
O4 C24 C25 C26 -58.3(3) . . . . ?
C23 C24 C25 C26 117.5(3) . . . . ?
C30 C25 C26 F13 175.8(2) . . . . ?
C24 C25 C26 F13 -0.6(3) . . . . ?
C30 C25 C26 C27 -0.7(4) . . . . ?
C24 C25 C26 C27 -177.2(2) . . . . ?
F13 C26 C27 F14 2.0(3) . . . . ?
C25 C26 C27 F14 178.6(2) . . . . ?
F13 C26 C27 C28 -176.2(2) . . . . ?
C25 C26 C27 C28 0.4(4) . . . . ?
F14 C27 C28 C29 -178.1(2) . . . . ?
C26 C27 C28 C29 0.1(4) . . . . ?
C27 C28 C29 F15 -179.7(2) . . . . ?
C27 C28 C29 C30 -0.2(4) . . . . ?
C26 C25 C30 F16 179.0(2) . . . . ?
C24 C25 C30 F16 -4.7(3) . . . . ?
C26 C25 C30 C29 0.5(3) . . . . ?
C24 C25 C30 C29 176.8(2) . . . . ?
F15 C29 C30 F16 0.9(3) . . . . ?
C28 C29 C30 F16 -178.6(2) . . . . ?
F15 C29 C30 C25 179.4(2) . . . . ?
C28 C29 C30 C25 -0.1(4) . . . . ?
C36 C31 C32 C33 1.2(4) . . . . ?
C37 C31 C32 C33 -178.1(3) . . . . ?
C31 C32 C33 C34 -1.5(4) . . . . ?
C32 C33 C34 C35 0.6(4) . . . . ?
C32 C33 C34 C38 -179.3(3) . . . . ?
C33 C34 C35 C36 0.5(4) . . . . ?
C38 C34 C35 C36 -179.6(3) . . . . ?
C34 C35 C36 C31 -0.7(4) . . . . ?
C32 C31 C36 C35 -0.1(4) . . . . ?
C37 C31 C36 C35 179.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.070
_database_code_depnum_ccdc_archive 'CCDC 895488'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_110201e1
#TrackingRef 'web_deposit_cif_file_4_AkikoHori_1344479419.110201e1.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H6 Cu F16 O4, 2(C7 H8)'
_chemical_formula_sum            'C44 H22 Cu F16 O4'
_chemical_formula_weight         982.17

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   8.0572(14)
_cell_length_b                   23.306(4)
_cell_length_c                   10.5652(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.830(2)
_cell_angle_gamma                90.00
_cell_volume                     1908.7(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    9602
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      27.70

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.709
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             982
_exptl_absorpt_coefficient_mu    0.697
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8181
_exptl_absorpt_correction_T_max  0.9026
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            20988
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0196
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.63
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4332
_reflns_number_gt                3811
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0359P)²+1.2846P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4332
_refine_ls_number_parameters     296
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.0801
_refine_ls_wR_factor_gt          0.0767
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.0000 0.5000 0.5000 0.01902(8) Uani 1 2 d S . .
O1 O 0.12377(15) 0.56645(5) 0.58328(11) 0.0210(2) Uani 1 1 d . . .
O2 O 0.03877(15) 0.51793(5) 0.33301(11) 0.0219(2) Uani 1 1 d . . .
C1 C 0.3936(2) 0.63645(8) 0.74478(17) 0.0244(3) Uani 1 1 d . . .
C2 C 0.4729(2) 0.67888(9) 0.83195(17) 0.0303(4) Uani 1 1 d . . .
C3 C 0.4543(2) 0.73571(9) 0.7982(2) 0.0333(4) Uani 1 1 d . . .
H3 H 0.5081 0.7647 0.8587 0.040 Uiso 1 1 calc R . .
C4 C 0.3552(2) 0.74953(8) 0.6739(2) 0.0312(4) Uani 1 1 d . . .
C5 C 0.2754(2) 0.70754(8) 0.58531(17) 0.0261(4) Uani 1 1 d . . .
C6 C 0.2914(2) 0.64993(7) 0.61900(16) 0.0215(3) Uani 1 1 d . . .
C7 C 0.1988(2) 0.60325(7) 0.52896(15) 0.0197(3) Uani 1 1 d . . .
C8 C 0.2026(2) 0.60323(7) 0.39791(16) 0.0223(3) Uani 1 1 d . . .
H8 H 0.2633 0.6329 0.3681 0.027 Uiso 1 1 calc R . .
C9 C 0.1203(2) 0.56115(7) 0.30898(15) 0.0201(3) Uani 1 1 d . . .
C10 C 0.1261(2) 0.56619(7) 0.16830(15) 0.0217(3) Uani 1 1 d . . .
C11 C 0.2040(2) 0.52458(7) 0.11084(16) 0.0236(3) Uani 1 1 d . . .
C12 C 0.2025(2) 0.52780(8) -0.02036(17) 0.0272(4) Uani 1 1 d . . .
C13 C 0.1188(2) 0.57171(8) -0.09935(17) 0.0287(4) Uani 1 1 d . . .
H13 H 0.1147 0.5733 -0.1900 0.034 Uiso 1 1 calc R . .
C14 C 0.0415(3) 0.61321(8) -0.04272(17) 0.0291(4) Uani 1 1 d . . .
C15 C 0.0460(2) 0.61113(7) 0.08900(16) 0.0253(4) Uani 1 1 d . . .
C16 C 0.7645(2) 0.65597(8) 0.38026(18) 0.0292(4) Uani 1 1 d . . .
H16 H 0.8044 0.6866 0.3369 0.035 Uiso 1 1 calc R . .
C17 C 0.7026(3) 0.60641(9) 0.31111(19) 0.0334(4) Uani 1 1 d . . .
H17 H 0.6989 0.6035 0.2207 0.040 Uiso 1 1 calc R . .
C18 C 0.6459(2) 0.56111(8) 0.3732(2) 0.0323(4) Uani 1 1 d . . .
H18 H 0.6034 0.5271 0.3259 0.039 Uiso 1 1 calc R . .
C19 C 0.6518(2) 0.56589(8) 0.50521(19) 0.0309(4) Uani 1 1 d . . .
H19 H 0.6138 0.5349 0.5487 0.037 Uiso 1 1 calc R . .
C20 C 0.7128(2) 0.61556(8) 0.57384(18) 0.0274(4) Uani 1 1 d . . .
H20 H 0.7162 0.6183 0.6642 0.033 Uiso 1 1 calc R . .
C21 C 0.7692(2) 0.66166(8) 0.51270(17) 0.0255(4) Uani 1 1 d . . .
C22 C 0.8327(3) 0.71616(8) 0.58735(19) 0.0341(4) Uani 1 1 d . . .
H22A H 0.7436 0.7311 0.6258 0.051 Uiso 1 1 calc R . .
H22B H 0.8579 0.7447 0.5271 0.051 Uiso 1 1 calc R . .
H22C H 0.9377 0.7081 0.6576 0.051 Uiso 1 1 calc R . .
F1 F 0.42201(14) 0.58162(4) 0.78167(10) 0.0303(2) Uani 1 1 d . . .
F2 F 0.57164(16) 0.66297(6) 0.95143(11) 0.0433(3) Uani 1 1 d . . .
F3 F 0.33311(16) 0.80483(5) 0.63681(13) 0.0446(3) Uani 1 1 d . . .
F4 F 0.17809(15) 0.72424(5) 0.46607(11) 0.0338(3) Uani 1 1 d . . .
F5 F -0.03155(15) 0.65296(4) 0.13931(10) 0.0335(3) Uani 1 1 d . . .
F6 F -0.04177(17) 0.65744(5) -0.11565(10) 0.0406(3) Uani 1 1 d . . .
F7 F 0.28161(15) 0.48616(5) -0.07029(11) 0.0365(3) Uani 1 1 d . . .
F8 F 0.28365(14) 0.48017(5) 0.18375(10) 0.0302(2) Uani 1 1 d . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O2 1.9197(11) 3_566 ?
Cu1 O2 1.9197(11) . ?
Cu1 O1 1.9206(11) 3_566 ?
Cu1 O1 1.9206(11) . ?
O1 C7 1.273(2) . ?
O2 C9 1.266(2) . ?
C1 F1 1.337(2) . ?
C1 C2 1.383(2) . ?
C1 C6 1.395(2) . ?
C2 F2 1.348(2) . ?
C2 C3 1.369(3) . ?
C3 C4 1.376(3) . ?
C3 H3 0.9500 . ?
C4 F3 1.345(2) . ?
C4 C5 1.385(3) . ?
C5 F4 1.347(2) . ?
C5 C6 1.386(2) . ?
C6 C7 1.503(2) . ?
C7 C8 1.393(2) . ?
C8 C9 1.394(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.504(2) . ?
C10 C11 1.382(2) . ?
C10 C15 1.386(2) . ?
C11 F8 1.344(2) . ?
C11 C12 1.385(2) . ?
C12 F7 1.345(2) . ?
C12 C13 1.375(3) . ?
C13 C14 1.373(3) . ?
C13 H13 0.9500 . ?
C14 F6 1.351(2) . ?
C14 C15 1.383(2) . ?
C15 F5 1.343(2) . ?
C16 C17 1.385(3) . ?
C16 C21 1.396(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.385(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.387(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.383(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.392(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.509(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 O2 180.00(7) 3_566 . ?
O2 Cu1 O1 92.93(5) 3_566 3_566 ?
O2 Cu1 O1 87.07(5) . 3_566 ?
O2 Cu1 O1 87.07(5) 3_566 . ?
O2 Cu1 O1 92.93(5) . . ?
O1 Cu1 O1 180.0 3_566 . ?
C7 O1 Cu1 126.01(10) . . ?
C9 O2 Cu1 125.53(10) . . ?
F1 C1 C2 118.55(16) . . ?
F1 C1 C6 120.16(15) . . ?
C2 C1 C6 121.24(17) . . ?
F2 C2 C3 120.31(17) . . ?
F2 C2 C1 118.32(18) . . ?
C3 C2 C1 121.36(17) . . ?
C2 C3 C4 117.95(17) . . ?
C2 C3 H3 121.0 . . ?
C4 C3 H3 121.0 . . ?
F3 C4 C3 119.91(17) . . ?
F3 C4 C5 118.69(18) . . ?
C3 C4 C5 121.40(18) . . ?
F4 C5 C4 118.18(16) . . ?
F4 C5 C6 120.65(15) . . ?
C4 C5 C6 121.15(17) . . ?
C5 C6 C1 116.89(15) . . ?
C5 C6 C7 122.92(15) . . ?
C1 C6 C7 120.14(15) . . ?
O1 C7 C8 126.14(15) . . ?
O1 C7 C6 114.66(14) . . ?
C8 C7 C6 119.20(15) . . ?
C7 C8 C9 122.33(16) . . ?
C7 C8 H8 118.8 . . ?
C9 C8 H8 118.8 . . ?
O2 C9 C8 127.01(15) . . ?
O2 C9 C10 114.70(14) . . ?
C8 C9 C10 118.29(15) . . ?
C11 C10 C15 117.19(15) . . ?
C11 C10 C9 121.29(15) . . ?
C15 C10 C9 121.43(15) . . ?
F8 C11 C10 119.44(15) . . ?
F8 C11 C12 119.18(15) . . ?
C10 C11 C12 121.38(16) . . ?
F7 C12 C13 120.34(15) . . ?
F7 C12 C11 118.55(17) . . ?
C13 C12 C11 121.09(16) . . ?
C14 C13 C12 117.75(16) . . ?
C14 C13 H13 121.1 . . ?
C12 C13 H13 121.1 . . ?
F6 C14 C13 120.19(16) . . ?
F6 C14 C15 118.27(16) . . ?
C13 C14 C15 121.54(17) . . ?
F5 C15 C14 119.03(15) . . ?
F5 C15 C10 119.96(14) . . ?
C14 C15 C10 121.00(16) . . ?
C17 C16 C21 121.03(17) . . ?
C17 C16 H16 119.5 . . ?
C21 C16 H16 119.5 . . ?
C18 C17 C16 120.25(18) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 119.35(18) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?
C20 C19 C18 120.29(18) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 121.12(17) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C20 C21 C16 117.95(17) . . ?
C20 C21 C22 120.94(16) . . ?
C16 C21 C22 121.10(17) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 Cu1 O1 C7 178.66(13) 3_566 . . . ?
O2 Cu1 O1 C7 -1.34(13) . . . . ?
O1 Cu1 O1 C7 31(3) 3_566 . . . ?
O2 Cu1 O2 C9 -74.5(17) 3_566 . . . ?
O1 Cu1 O2 C9 179.58(13) 3_566 . . . ?
O1 Cu1 O2 C9 -0.42(13) . . . . ?
F1 C1 C2 F2 -1.7(2) . . . . ?
C6 C1 C2 F2 -179.22(15) . . . . ?
F1 C1 C2 C3 177.48(16) . . . . ?
C6 C1 C2 C3 -0.1(3) . . . . ?
F2 C2 C3 C4 178.52(17) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C2 C3 C4 F3 179.78(17) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
F3 C4 C5 F4 -0.4(3) . . . . ?
C3 C4 C5 F4 178.95(17) . . . . ?
F3 C4 C5 C6 -178.93(16) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
F4 C5 C6 C1 -179.56(15) . . . . ?
C4 C5 C6 C1 -1.1(3) . . . . ?
F4 C5 C6 C7 -2.1(3) . . . . ?
C4 C5 C6 C7 176.35(16) . . . . ?
F1 C1 C6 C5 -176.60(15) . . . . ?
C2 C1 C6 C5 0.9(2) . . . . ?
F1 C1 C6 C7 5.9(2) . . . . ?
C2 C1 C6 C7 -176.60(15) . . . . ?
Cu1 O1 C7 C8 1.6(2) . . . . ?
Cu1 O1 C7 C6 -177.93(10) . . . . ?
C5 C6 C7 O1 -132.90(17) . . . . ?
C1 C6 C7 O1 44.4(2) . . . . ?
C5 C6 C7 C8 47.6(2) . . . . ?
C1 C6 C7 C8 -135.08(17) . . . . ?
O1 C7 C8 C9 0.2(3) . . . . ?
C6 C7 C8 C9 179.71(15) . . . . ?
Cu1 O2 C9 C8 2.1(2) . . . . ?
Cu1 O2 C9 C10 -177.79(10) . . . . ?
C7 C8 C9 O2 -2.3(3) . . . . ?
C7 C8 C9 C10 177.66(15) . . . . ?
O2 C9 C10 C11 -62.0(2) . . . . ?
C8 C9 C10 C11 118.06(18) . . . . ?
O2 C9 C10 C15 114.64(18) . . . . ?
C8 C9 C10 C15 -65.3(2) . . . . ?
C15 C10 C11 F8 179.89(15) . . . . ?
C9 C10 C11 F8 -3.3(2) . . . . ?
C15 C10 C11 C12 0.2(3) . . . . ?
C9 C10 C11 C12 176.99(16) . . . . ?
F8 C11 C12 F7 -0.1(2) . . . . ?
C10 C11 C12 F7 179.56(15) . . . . ?
F8 C11 C12 C13 178.34(16) . . . . ?
C10 C11 C12 C13 -2.0(3) . . . . ?
F7 C12 C13 C14 -179.55(16) . . . . ?
C11 C12 C13 C14 2.0(3) . . . . ?
C12 C13 C14 F6 179.68(17) . . . . ?
C12 C13 C14 C15 -0.4(3) . . . . ?
F6 C14 C15 F5 -0.2(3) . . . . ?
C13 C14 C15 F5 179.86(17) . . . . ?
F6 C14 C15 C10 178.56(16) . . . . ?
C13 C14 C15 C10 -1.4(3) . . . . ?
C11 C10 C15 F5 -179.83(16) . . . . ?
C9 C10 C15 F5 3.4(3) . . . . ?
C11 C10 C15 C14 1.4(3) . . . . ?
C9 C10 C15 C14 -175.34(16) . . . . ?
C21 C16 C17 C18 -0.8(3) . . . . ?
C16 C17 C18 C19 0.0(3) . . . . ?
C17 C18 C19 C20 0.4(3) . . . . ?
C18 C19 C20 C21 0.0(3) . . . . ?
C19 C20 C21 C16 -0.8(3) . . . . ?
C19 C20 C21 C22 178.92(17) . . . . ?
C17 C16 C21 C20 1.2(3) . . . . ?
C17 C16 C21 C22 -178.54(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.052


_database_code_depnum_ccdc_archive 'CCDC 895489'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_110905b2
#TrackingRef 'web_deposit_cif_file_0_AkikoHori_1344479752.110905b2.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H10 Cu F12 O4'
_chemical_formula_sum            'C30 H10 Cu F12 O4'
_chemical_formula_weight         725.93

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.225(2)
_cell_length_b                   10.922(4)
_cell_length_c                   16.756(5)
_cell_angle_alpha                88.023(4)
_cell_angle_beta                 86.760(3)
_cell_angle_gamma                86.128(4)
_cell_volume                     1316.5(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    6437
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      27.94

_exptl_crystal_description       prismatic
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.831
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             718
_exptl_absorpt_coefficient_mu    0.954
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8034
_exptl_absorpt_correction_T_max  0.9106
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            14887
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         27.48
_reflns_number_total             5890
_reflns_number_gt                4918
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0355P)²+0.6916P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5890
_refine_ls_number_parameters     427
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0291
_refine_ls_wR_factor_ref         0.0752
_refine_ls_wR_factor_gt          0.0707
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.5000 0.5000 0.0000 0.01752(8) Uani 1 2 d S . .
Cu2 Cu 1.0000 0.0000 0.5000 0.01477(8) Uani 1 2 d S . .
O1 O 0.30152(17) 0.62039(12) -0.01822(7) 0.0207(3) Uani 1 1 d . . .
O2 O 0.40355(17) 0.45523(12) 0.10465(7) 0.0207(3) Uani 1 1 d . . .
O3 O 0.91056(17) 0.12497(11) 0.42608(7) 0.0188(3) Uani 1 1 d . . .
O4 O 0.80008(17) 0.03246(11) 0.57862(7) 0.0179(3) Uani 1 1 d . . .
C1 C 0.0679(3) 0.83775(18) -0.04953(11) 0.0219(4) Uani 1 1 d . . .
C2 C -0.0574(3) 0.92621(18) -0.07892(12) 0.0268(4) Uani 1 1 d . . .
H2 H -0.0179 0.9939 -0.1111 0.032 Uiso 1 1 calc R . .
C3 C -0.2423(3) 0.91195(19) -0.05951(12) 0.0269(4) Uani 1 1 d . . .
C4 C -0.3058(3) 0.81442(19) -0.01507(11) 0.0239(4) Uani 1 1 d . . .
H4 H -0.4347 0.8057 -0.0037 0.029 Uiso 1 1 calc R . .
C5 C -0.1726(3) 0.72965(17) 0.01230(10) 0.0190(4) Uani 1 1 d . . .
C6 C 0.0185(2) 0.73630(16) -0.00223(10) 0.0172(4) Uani 1 1 d . . .
C7 C 0.1601(2) 0.64314(16) 0.02921(11) 0.0179(4) Uani 1 1 d . . .
C8 C 0.1322(3) 0.59139(17) 0.10604(11) 0.0199(4) Uani 1 1 d . . .
H8 H 0.0225 0.6165 0.1368 0.024 Uiso 1 1 calc R . .
C9 C 0.2583(2) 0.50440(17) 0.13985(10) 0.0181(4) Uani 1 1 d . . .
C10 C 0.2229(2) 0.46187(17) 0.22530(10) 0.0185(4) Uani 1 1 d . . .
C11 C 0.2447(3) 0.33911(18) 0.25032(11) 0.0222(4) Uani 1 1 d . . .
C12 C 0.2185(3) 0.29686(19) 0.32859(11) 0.0244(4) Uani 1 1 d . . .
H12 H 0.2326 0.2120 0.3430 0.029 Uiso 1 1 calc R . .
C13 C 0.1710(3) 0.38416(19) 0.38435(11) 0.0232(4) Uani 1 1 d . . .
C14 C 0.1482(3) 0.50721(19) 0.36591(11) 0.0249(4) Uani 1 1 d . . .
H14 H 0.1153 0.5654 0.4060 0.030 Uiso 1 1 calc R . .
C15 C 0.1751(3) 0.54278(18) 0.28647(11) 0.0222(4) Uani 1 1 d . . .
C16 C 0.7446(3) 0.27333(17) 0.29332(11) 0.0205(4) Uani 1 1 d . . .
C17 C 0.7196(3) 0.36443(18) 0.23476(11) 0.0226(4) Uani 1 1 d . . .
H17 H 0.7295 0.3470 0.1795 0.027 Uiso 1 1 calc R . .
C18 C 0.6795(3) 0.48174(18) 0.26106(11) 0.0220(4) Uani 1 1 d . . .
C19 C 0.6609(3) 0.51054(17) 0.34041(12) 0.0223(4) Uani 1 1 d . . .
H19 H 0.6321 0.5924 0.3567 0.027 Uiso 1 1 calc R . .
C20 C 0.6862(2) 0.41485(18) 0.39500(11) 0.0197(4) Uani 1 1 d . . .
C21 C 0.7292(2) 0.29373(17) 0.37516(10) 0.0168(4) Uani 1 1 d . . .
C22 C 0.7631(2) 0.19419(16) 0.43734(10) 0.0166(4) Uani 1 1 d . . .
C23 C 0.6341(3) 0.18657(17) 0.50221(11) 0.0198(4) Uani 1 1 d . . .
H23 H 0.5228 0.2380 0.5012 0.024 Uiso 1 1 calc R . .
C24 C 0.6596(2) 0.10744(16) 0.56847(11) 0.0164(3) Uani 1 1 d . . .
C25 C 0.5142(2) 0.11394(16) 0.63578(10) 0.0167(4) Uani 1 1 d . . .
C26 C 0.5591(2) 0.11220(17) 0.71596(11) 0.0196(4) Uani 1 1 d . . .
C27 C 0.4292(3) 0.12891(17) 0.77862(11) 0.0216(4) Uani 1 1 d . . .
H27 H 0.4649 0.1304 0.8323 0.026 Uiso 1 1 calc R . .
C28 C 0.2459(3) 0.14330(17) 0.76047(11) 0.0196(4) Uani 1 1 d . . .
C29 C 0.1865(2) 0.14138(16) 0.68400(11) 0.0188(4) Uani 1 1 d . . .
H29 H 0.0585 0.1491 0.6732 0.023 Uiso 1 1 calc R . .
C30 C 0.3239(2) 0.12759(16) 0.62396(10) 0.0164(4) Uani 1 1 d . . .
F1 F 0.24957(16) 0.85528(11) -0.06533(8) 0.0325(3) Uani 1 1 d . . .
F2 F -0.36800(18) 0.99845(13) -0.08611(8) 0.0426(3) Uani 1 1 d . . .
F3 F -0.23478(15) 0.63180(10) 0.05495(7) 0.0261(3) Uani 1 1 d . . .
F4 F 0.28837(19) 0.25451(11) 0.19489(7) 0.0352(3) Uani 1 1 d . . .
F5 F 0.14264(18) 0.34692(12) 0.46167(7) 0.0332(3) Uani 1 1 d . . .
F6 F 0.15779(19) 0.66399(11) 0.26832(7) 0.0354(3) Uani 1 1 d . . .
F7 F 0.78177(18) 0.15758(10) 0.26972(7) 0.0322(3) Uani 1 1 d . . .
F8 F 0.65655(18) 0.57420(11) 0.20651(7) 0.0327(3) Uani 1 1 d . . .
F9 F 0.67542(17) 0.44285(10) 0.47318(6) 0.0300(3) Uani 1 1 d . . .
F10 F 0.73854(15) 0.09757(11) 0.73343(6) 0.0277(3) Uani 1 1 d . . .
F11 F 0.11661(15) 0.16032(11) 0.82119(6) 0.0258(3) Uani 1 1 d . . .
F12 F 0.26795(14) 0.12652(10) 0.54847(6) 0.0223(2) Uani 1 1 d . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.9093(13) 2_665 ?
Cu1 O1 1.9093(13) . ?
Cu1 O2 1.9099(13) 2_665 ?
Cu1 O2 1.9100(13) . ?
Cu2 O3 1.9156(13) . ?
Cu2 O3 1.9156(13) 2_756 ?
Cu2 O4 1.9223(13) . ?
Cu2 O4 1.9223(13) 2_756 ?
O1 C7 1.275(2) . ?
O2 C9 1.270(2) . ?
O3 C22 1.273(2) . ?
O4 C24 1.276(2) . ?
C1 F1 1.349(2) . ?
C1 C2 1.376(3) . ?
C1 C6 1.394(3) . ?
C2 C3 1.375(3) . ?
C2 H2 0.9500 . ?
C3 F2 1.348(2) . ?
C3 C4 1.368(3) . ?
C4 C5 1.376(3) . ?
C4 H4 0.9500 . ?
C5 F3 1.353(2) . ?
C5 C6 1.394(3) . ?
C6 C7 1.498(2) . ?
C7 C8 1.398(3) . ?
C8 C9 1.399(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.503(2) . ?
C10 C15 1.390(3) . ?
C10 C11 1.392(3) . ?
C11 F4 1.343(2) . ?
C11 C12 1.382(3) . ?
C12 C13 1.371(3) . ?
C12 H12 0.9500 . ?
C13 F5 1.353(2) . ?
C13 C14 1.370(3) . ?
C14 C15 1.380(3) . ?
C14 H14 0.9500 . ?
C15 F6 1.347(2) . ?
C16 F7 1.343(2) . ?
C16 C17 1.383(3) . ?
C16 C21 1.394(3) . ?
C17 C18 1.376(3) . ?
C17 H17 0.9500 . ?
C18 F8 1.347(2) . ?
C18 C19 1.374(3) . ?
C19 C20 1.375(3) . ?
C19 H19 0.9500 . ?
C20 F9 1.352(2) . ?
C20 C21 1.386(3) . ?
C21 C22 1.497(2) . ?
C22 C23 1.395(2) . ?
C23 C24 1.396(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.497(2) . ?
C25 C30 1.397(2) . ?
C25 C26 1.399(2) . ?
C26 F10 1.343(2) . ?
C26 C27 1.377(3) . ?
C27 C28 1.373(3) . ?
C27 H27 0.9500 . ?
C28 F11 1.351(2) . ?
C28 C29 1.375(3) . ?
C29 C30 1.378(2) . ?
C29 H29 0.9500 . ?
C30 F12 1.350(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 180.0 2_665 . ?
O1 Cu1 O2 93.76(5) 2_665 2_665 ?
O1 Cu1 O2 86.24(5) . 2_665 ?
O1 Cu1 O2 86.24(5) 2_665 . ?
O1 Cu1 O2 93.76(5) . . ?
O2 Cu1 O2 180.00(3) 2_665 . ?
O3 Cu2 O3 180.0 . 2_756 ?
O3 Cu2 O4 94.10(5) . . ?
O3 Cu2 O4 85.90(5) 2_756 . ?
O3 Cu2 O4 85.90(5) . 2_756 ?
O3 Cu2 O4 94.10(5) 2_756 2_756 ?
O4 Cu2 O4 180.0 . 2_756 ?
C7 O1 Cu1 125.73(11) . . ?
C9 O2 Cu1 125.46(12) . . ?
C22 O3 Cu2 125.03(11) . . ?
C24 O4 Cu2 124.86(11) . . ?
F1 C1 C2 116.68(17) . . ?
F1 C1 C6 119.06(16) . . ?
C2 C1 C6 124.19(18) . . ?
C3 C2 C1 116.86(18) . . ?
C3 C2 H2 121.6 . . ?
C1 C2 H2 121.6 . . ?
F2 C3 C4 118.21(18) . . ?
F2 C3 C2 118.18(19) . . ?
C4 C3 C2 123.61(18) . . ?
C3 C4 C5 116.27(18) . . ?
C3 C4 H4 121.9 . . ?
C5 C4 H4 121.9 . . ?
F3 C5 C4 116.49(16) . . ?
F3 C5 C6 118.53(16) . . ?
C4 C5 C6 124.96(17) . . ?
C5 C6 C1 114.08(16) . . ?
C5 C6 C7 123.66(16) . . ?
C1 C6 C7 122.26(16) . . ?
O1 C7 C8 125.56(16) . . ?
O1 C7 C6 114.78(15) . . ?
C8 C7 C6 119.63(16) . . ?
C7 C8 C9 123.09(17) . . ?
C7 C8 H8 118.5 . . ?
C9 C8 H8 118.5 . . ?
O2 C9 C8 125.97(16) . . ?
O2 C9 C10 115.11(15) . . ?
C8 C9 C10 118.92(16) . . ?
C15 C10 C11 114.50(17) . . ?
C15 C10 C9 122.58(17) . . ?
C11 C10 C9 122.84(17) . . ?
F4 C11 C12 117.02(18) . . ?
F4 C11 C10 118.41(16) . . ?
C12 C11 C10 124.54(18) . . ?
C13 C12 C11 116.36(18) . . ?
C13 C12 H12 121.8 . . ?
C11 C12 H12 121.8 . . ?
F5 C13 C14 118.04(18) . . ?
F5 C13 C12 118.41(18) . . ?
C14 C13 C12 123.54(18) . . ?
C13 C14 C15 116.98(18) . . ?
C13 C14 H14 121.5 . . ?
C15 C14 H14 121.5 . . ?
F6 C15 C14 117.20(17) . . ?
F6 C15 C10 118.70(17) . . ?
C14 C15 C10 124.08(18) . . ?
F7 C16 C17 117.81(17) . . ?
F7 C16 C21 118.04(16) . . ?
C17 C16 C21 124.14(18) . . ?
C18 C17 C16 116.28(18) . . ?
C18 C17 H17 121.9 . . ?
C16 C17 H17 121.9 . . ?
F8 C18 C19 117.60(18) . . ?
F8 C18 C17 118.72(17) . . ?
C19 C18 C17 123.68(17) . . ?
C18 C19 C20 116.57(18) . . ?
C18 C19 H19 121.7 . . ?
C20 C19 H19 121.7 . . ?
F9 C20 C19 117.05(17) . . ?
F9 C20 C21 118.34(16) . . ?
C19 C20 C21 124.55(17) . . ?
C20 C21 C16 114.77(16) . . ?
C20 C21 C22 122.08(16) . . ?
C16 C21 C22 123.11(16) . . ?
O3 C22 C23 126.09(16) . . ?
O3 C22 C21 115.99(15) . . ?
C23 C22 C21 117.91(16) . . ?
C22 C23 C24 123.57(17) . . ?
C22 C23 H23 118.2 . . ?
C24 C23 H23 118.2 . . ?
O4 C24 C23 125.86(16) . . ?
O4 C24 C25 116.30(15) . . ?
C23 C24 C25 117.78(15) . . ?
C30 C25 C26 114.52(16) . . ?
C30 C25 C24 123.12(16) . . ?
C26 C25 C24 122.30(16) . . ?
F10 C26 C27 117.56(16) . . ?
F10 C26 C25 118.90(16) . . ?
C27 C26 C25 123.51(17) . . ?
C28 C27 C26 117.31(17) . . ?
C28 C27 H27 121.3 . . ?
C26 C27 H27 121.3 . . ?
F11 C28 C27 118.11(17) . . ?
F11 C28 C29 118.15(16) . . ?
C27 C28 C29 123.73(17) . . ?
C28 C29 C30 115.95(17) . . ?
C28 C29 H29 122.0 . . ?
C30 C29 H29 122.0 . . ?
F12 C30 C29 116.67(15) . . ?
F12 C30 C25 118.44(15) . . ?
C29 C30 C25 124.88(17) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 Cu1 O1 C7 92(5) 2_665 . . . ?
O2 Cu1 O1 C7 176.36(15) 2_665 . . . ?
O2 Cu1 O1 C7 -3.64(15) . . . . ?
O1 Cu1 O2 C9 177.64(15) 2_665 . . . ?
O1 Cu1 O2 C9 -2.36(15) . . . . ?
O2 Cu1 O2 C9 -157(20) 2_665 . . . ?
O3 Cu2 O3 C22 3(29) 2_756 . . . ?
O4 Cu2 O3 C22 -0.87(14) . . . . ?
O4 Cu2 O3 C22 179.13(14) 2_756 . . . ?
O3 Cu2 O4 C24 6.02(14) . . . . ?
O3 Cu2 O4 C24 -173.98(14) 2_756 . . . ?
O4 Cu2 O4 C24 -31(6) 2_756 . . . ?
F1 C1 C2 C3 -176.77(18) . . . . ?
C6 C1 C2 C3 0.2(3) . . . . ?
C1 C2 C3 F2 178.69(18) . . . . ?
C1 C2 C3 C4 -1.7(3) . . . . ?
F2 C3 C4 C5 -178.65(17) . . . . ?
C2 C3 C4 C5 1.7(3) . . . . ?
C3 C4 C5 F3 -178.75(17) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
F3 C5 C6 C1 177.37(16) . . . . ?
C4 C5 C6 C1 -1.1(3) . . . . ?
F3 C5 C6 C7 -2.2(3) . . . . ?
C4 C5 C6 C7 179.30(18) . . . . ?
F1 C1 C6 C5 178.00(16) . . . . ?
C2 C1 C6 C5 1.1(3) . . . . ?
F1 C1 C6 C7 -2.4(3) . . . . ?
C2 C1 C6 C7 -179.25(18) . . . . ?
Cu1 O1 C7 C8 5.7(3) . . . . ?
Cu1 O1 C7 C6 -175.96(11) . . . . ?
C5 C6 C7 O1 143.43(18) . . . . ?
C1 C6 C7 O1 -36.1(2) . . . . ?
C5 C6 C7 C8 -38.1(3) . . . . ?
C1 C6 C7 C8 142.29(19) . . . . ?
O1 C7 C8 C9 -1.4(3) . . . . ?
C6 C7 C8 C9 -179.66(17) . . . . ?
Cu1 O2 C9 C8 6.8(3) . . . . ?
Cu1 O2 C9 C10 -173.78(12) . . . . ?
C7 C8 C9 O2 -5.4(3) . . . . ?
C7 C8 C9 C10 175.17(18) . . . . ?
O2 C9 C10 C15 133.54(19) . . . . ?
C8 C9 C10 C15 -47.0(3) . . . . ?
O2 C9 C10 C11 -43.1(3) . . . . ?
C8 C9 C10 C11 136.42(19) . . . . ?
C15 C10 C11 F4 179.08(17) . . . . ?
C9 C10 C11 F4 -4.1(3) . . . . ?
C15 C10 C11 C12 1.3(3) . . . . ?
C9 C10 C11 C12 178.14(18) . . . . ?
F4 C11 C12 C13 -178.99(17) . . . . ?
C10 C11 C12 C13 -1.2(3) . . . . ?
C11 C12 C13 F5 179.52(17) . . . . ?
C11 C12 C13 C14 0.5(3) . . . . ?
F5 C13 C14 C15 -179.03(17) . . . . ?
C12 C13 C14 C15 0.0(3) . . . . ?
C13 C14 C15 F6 -178.22(17) . . . . ?
C13 C14 C15 C10 0.1(3) . . . . ?
C11 C10 C15 F6 177.58(17) . . . . ?
C9 C10 C15 F6 0.7(3) . . . . ?
C11 C10 C15 C14 -0.7(3) . . . . ?
C9 C10 C15 C14 -177.59(18) . . . . ?
F7 C16 C17 C18 179.24(17) . . . . ?
C21 C16 C17 C18 0.8(3) . . . . ?
C16 C17 C18 F8 179.02(16) . . . . ?
C16 C17 C18 C19 -1.1(3) . . . . ?
F8 C18 C19 C20 -179.55(16) . . . . ?
C17 C18 C19 C20 0.6(3) . . . . ?
C18 C19 C20 F9 177.51(16) . . . . ?
C18 C19 C20 C21 0.3(3) . . . . ?
F9 C20 C21 C16 -177.69(16) . . . . ?
C19 C20 C21 C16 -0.5(3) . . . . ?
F9 C20 C21 C22 0.2(3) . . . . ?
C19 C20 C21 C22 177.35(17) . . . . ?
F7 C16 C21 C20 -178.49(16) . . . . ?
C17 C16 C21 C20 -0.1(3) . . . . ?
F7 C16 C21 C22 3.7(3) . . . . ?
C17 C16 C21 C22 -177.92(18) . . . . ?
Cu2 O3 C22 C23 -4.7(3) . . . . ?
Cu2 O3 C22 C21 174.29(11) . . . . ?
C20 C21 C22 O3 -130.14(18) . . . . ?
C16 C21 C22 O3 47.5(2) . . . . ?
C20 C21 C22 C23 48.9(2) . . . . ?
C16 C21 C22 C23 -133.44(19) . . . . ?
O3 C22 C23 C24 6.4(3) . . . . ?
C21 C22 C23 C24 -172.54(17) . . . . ?
Cu2 O4 C24 C23 -6.1(3) . . . . ?
Cu2 O4 C24 C25 176.70(11) . . . . ?
C22 C23 C24 O4 -0.4(3) . . . . ?
C22 C23 C24 C25 176.70(17) . . . . ?
O4 C24 C25 C30 -141.78(18) . . . . ?
C23 C24 C25 C30 40.8(3) . . . . ?
O4 C24 C25 C26 41.1(2) . . . . ?
C23 C24 C25 C26 -136.28(19) . . . . ?
C30 C25 C26 F10 179.00(16) . . . . ?
C24 C25 C26 F10 -3.7(3) . . . . ?
C30 C25 C26 C27 -3.3(3) . . . . ?
C24 C25 C26 C27 174.05(17) . . . . ?
F10 C26 C27 C28 -179.73(16) . . . . ?
C25 C26 C27 C28 2.5(3) . . . . ?
C26 C27 C28 F11 -179.72(16) . . . . ?
C26 C27 C28 C29 0.3(3) . . . . ?
F11 C28 C29 C30 178.06(15) . . . . ?
C27 C28 C29 C30 -1.9(3) . . . . ?
C28 C29 C30 F12 -179.48(15) . . . . ?
C28 C29 C30 C25 1.0(3) . . . . ?
C26 C25 C30 F12 -178.05(15) . . . . ?
C24 C25 C30 F12 4.6(3) . . . . ?
C26 C25 C30 C29 1.4(3) . . . . ?
C24 C25 C30 C29 -175.86(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.973
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.973
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.058
_database_code_depnum_ccdc_archive 'CCDC 895491'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_100308b1
#TrackingRef 'web_deposit_cif_file_1_AkikoHori_1344479752.100308b1.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H10 Cu F12 O4, 2(C6 H6)'
_chemical_formula_sum            'C42 H22 Cu F12 O4'
_chemical_formula_weight         882.15

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/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                   8.7060(14)
_cell_length_b                   17.782(3)
_cell_length_c                   23.038(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.888(2)
_cell_angle_gamma                90.00
_cell_volume                     3513.5(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    5944
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      27.82

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1772
_exptl_absorpt_coefficient_mu    0.731
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7839
_exptl_absorpt_correction_T_max  0.9438
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            19047
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_sigmaI/netI    0.0331
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.29
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4000
_reflns_number_gt                3257
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0446P)²+9.0062P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4000
_refine_ls_number_parameters     267
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1069
_refine_ls_wR_factor_gt          0.0999
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.5000 0.88666(2) 0.7500 0.01584(11) Uani 1 2 d S . .
F1 F 0.15633(16) 0.70031(8) 0.73499(6) 0.0250(3) Uani 1 1 d . . .
F4 F 0.17138(16) 1.07120(8) 0.74264(6) 0.0252(3) Uani 1 1 d . . .
C14 C 0.0548(3) 1.10632(13) 0.56450(11) 0.0230(5) Uani 1 1 d . . .
H14 H 0.0252 1.1142 0.5233 0.028 Uiso 1 1 calc R . .
F6 F 0.15132(17) 0.98732(8) 0.54816(6) 0.0268(3) Uani 1 1 d . . .
F2 F -0.03920(18) 0.55624(8) 0.56885(7) 0.0345(4) Uani 1 1 d . . .
F3 F 0.17613(17) 0.79269(8) 0.54557(6) 0.0260(3) Uani 1 1 d . . .
O1 O 0.37706(18) 0.80800(8) 0.70764(7) 0.0193(3) Uani 1 1 d . . .
O2 O 0.37843(18) 0.96584(8) 0.70806(7) 0.0192(3) Uani 1 1 d . . .
C7 C 0.2560(3) 0.81852(12) 0.66866(10) 0.0178(4) Uani 1 1 d . . .
C9 C 0.2548(2) 0.95622(12) 0.67004(10) 0.0167(4) Uani 1 1 d . . .
C6 C 0.1753(3) 0.74904(12) 0.64198(10) 0.0187(5) Uani 1 1 d . . .
C10 C 0.1726(3) 1.02672(12) 0.64687(10) 0.0181(4) Uani 1 1 d . . .
C11 C 0.1379(3) 1.08331(13) 0.68416(10) 0.0199(5) Uani 1 1 d . . .
C1 C 0.1309(3) 0.69121(13) 0.67608(10) 0.0200(5) Uani 1 1 d . . .
C5 C 0.1392(3) 0.73838(13) 0.58134(10) 0.0208(5) Uani 1 1 d . . .
C8 C 0.1909(3) 0.88769(12) 0.64937(10) 0.0194(4) Uani 1 1 d . . .
H8 H 0.0983 0.8880 0.6207 0.023 Uiso 1 1 calc R . .
C3 C 0.0301(3) 0.61940(13) 0.59301(12) 0.0255(5) Uani 1 1 d . . .
C4 C 0.0693(3) 0.67378(14) 0.55536(11) 0.0251(5) Uani 1 1 d . . .
H4 H 0.0495 0.6673 0.5138 0.030 Uiso 1 1 calc R . .
C2 C 0.0572(3) 0.62589(13) 0.65327(12) 0.0238(5) Uani 1 1 d . . .
H2 H 0.0272 0.5878 0.6780 0.029 Uiso 1 1 calc R . .
C15 C 0.1246(3) 1.04063(13) 0.58693(10) 0.0206(5) Uani 1 1 d . . .
C12 C 0.0676(3) 1.15082(13) 0.66512(11) 0.0221(5) Uani 1 1 d . . .
H12 H 0.0465 1.1885 0.6919 0.027 Uiso 1 1 calc R . .
C13 C 0.0300(3) 1.16020(13) 0.60495(11) 0.0217(5) Uani 1 1 d . . .
F5 F -0.03329(16) 1.22642(8) 0.58421(6) 0.0282(3) Uani 1 1 d . . .
C18 C 0.1925(4) 0.9114(3) 0.82169(16) 0.0575(10) Uani 1 1 d . . .
H18 H 0.1770 0.9304 0.7826 0.069 Uiso 1 1 calc R . .
C21 C 0.2359(4) 0.8567(4) 0.93375(16) 0.0740(16) Uani 1 1 d . . .
H21 H 0.2517 0.8379 0.9729 0.089 Uiso 1 1 calc R . .
C20 C 0.2396(3) 0.9352(2) 0.92374(15) 0.0477(9) Uani 1 1 d . . .
H20 H 0.2583 0.9702 0.9553 0.057 Uiso 1 1 calc R . .
C16 C 0.2109(4) 0.8100(2) 0.8893(3) 0.090(2) Uani 1 1 d . . .
H16 H 0.2061 0.7574 0.8961 0.108 Uiso 1 1 calc R . .
C19 C 0.2147(4) 0.9582(2) 0.8657(2) 0.0587(11) Uani 1 1 d . . .
H19 H 0.2138 1.0106 0.8575 0.070 Uiso 1 1 calc R . .
C17 C 0.1909(4) 0.8383(3) 0.8303(2) 0.0668(12) Uani 1 1 d . . .
H17 H 0.1767 0.8047 0.7977 0.080 Uiso 1 1 calc R . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O2 1.9194(16) 2_656 ?
Cu1 O2 1.9195(15) . ?
Cu1 O1 1.9224(16) 2_656 ?
Cu1 O1 1.9224(16) . ?
F1 C1 1.347(3) . ?
F4 C11 1.346(3) . ?
C14 C15 1.376(3) . ?
C14 C13 1.379(3) . ?
C14 H14 0.9500 . ?
F6 C15 1.350(3) . ?
F2 C3 1.349(3) . ?
F3 C5 1.344(3) . ?
O1 C7 1.276(3) . ?
O2 C9 1.277(3) . ?
C7 C8 1.395(3) . ?
C7 C6 1.500(3) . ?
C9 C8 1.390(3) . ?
C9 C10 1.496(3) . ?
C6 C1 1.389(3) . ?
C6 C5 1.391(3) . ?
C10 C11 1.390(3) . ?
C10 C15 1.395(3) . ?
C11 C12 1.384(3) . ?
C1 C2 1.386(3) . ?
C5 C4 1.387(3) . ?
C8 H8 0.9500 . ?
C3 C2 1.373(4) . ?
C3 C4 1.381(4) . ?
C4 H4 0.9500 . ?
C2 H2 0.9500 . ?
C12 C13 1.379(3) . ?
C12 H12 0.9500 . ?
C13 F5 1.352(3) . ?
C18 C19 1.299(6) . ?
C18 C17 1.316(6) . ?
C18 H18 0.9500 . ?
C21 C16 1.309(7) . ?
C21 C20 1.416(7) . ?
C21 H21 0.9500 . ?
C20 C19 1.380(5) . ?
C20 H20 0.9500 . ?
C16 C17 1.432(7) . ?
C16 H16 0.9500 . ?
C19 H19 0.9500 . ?
C17 H17 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 O2 85.65(9) 2_656 . ?
O2 Cu1 O1 93.86(6) 2_656 2_656 ?
O2 Cu1 O1 179.51(7) . 2_656 ?
O2 Cu1 O1 179.51(7) 2_656 . ?
O2 Cu1 O1 93.86(7) . . ?
O1 Cu1 O1 86.63(9) 2_656 . ?
C15 C14 C13 116.5(2) . . ?
C15 C14 H14 121.7 . . ?
C13 C14 H14 121.7 . . ?
C7 O1 Cu1 124.85(14) . . ?
C9 O2 Cu1 125.02(14) . . ?
O1 C7 C8 126.5(2) . . ?
O1 C7 C6 116.10(19) . . ?
C8 C7 C6 117.38(19) . . ?
O2 C9 C8 126.4(2) . . ?
O2 C9 C10 115.33(19) . . ?
C8 C9 C10 118.27(19) . . ?
C1 C6 C5 115.5(2) . . ?
C1 C6 C7 122.3(2) . . ?
C5 C6 C7 122.2(2) . . ?
C11 C10 C15 115.1(2) . . ?
C11 C10 C9 121.9(2) . . ?
C15 C10 C9 123.1(2) . . ?
F4 C11 C12 117.6(2) . . ?
F4 C11 C10 118.1(2) . . ?
C12 C11 C10 124.3(2) . . ?
F1 C1 C2 117.9(2) . . ?
F1 C1 C6 117.9(2) . . ?
C2 C1 C6 124.2(2) . . ?
F3 C5 C4 117.6(2) . . ?
F3 C5 C6 118.8(2) . . ?
C4 C5 C6 123.6(2) . . ?
C9 C8 C7 123.2(2) . . ?
C9 C8 H8 118.4 . . ?
C7 C8 H8 118.4 . . ?
F2 C3 C2 118.3(2) . . ?
F2 C3 C4 117.7(2) . . ?
C2 C3 C4 124.0(2) . . ?
C3 C4 C5 116.5(2) . . ?
C3 C4 H4 121.7 . . ?
C5 C4 H4 121.7 . . ?
C3 C2 C1 116.2(2) . . ?
C3 C2 H2 121.9 . . ?
C1 C2 H2 121.9 . . ?
F6 C15 C14 117.6(2) . . ?
F6 C15 C10 118.3(2) . . ?
C14 C15 C10 124.1(2) . . ?
C13 C12 C11 116.1(2) . . ?
C13 C12 H12 122.0 . . ?
C11 C12 H12 122.0 . . ?
F5 C13 C12 118.2(2) . . ?
F5 C13 C14 117.9(2) . . ?
C12 C13 C14 123.9(2) . . ?
C19 C18 C17 121.3(4) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C16 C21 C20 120.3(4) . . ?
C16 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C19 C20 C21 116.5(3) . . ?
C19 C20 H20 121.8 . . ?
C21 C20 H20 121.8 . . ?
C21 C16 C17 119.7(4) . . ?
C21 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C18 C19 C20 123.0(3) . . ?
C18 C19 H19 118.5 . . ?
C20 C19 H19 118.5 . . ?
C18 C17 C16 119.2(4) . . ?
C18 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 Cu1 O1 C7 0(9) 2_656 . . . ?
O2 Cu1 O1 C7 -2.78(18) . . . . ?
O1 Cu1 O1 C7 177.2(2) 2_656 . . . ?
O2 Cu1 O2 C9 -175.3(2) 2_656 . . . ?
O1 Cu1 O2 C9 -179(100) 2_656 . . . ?
O1 Cu1 O2 C9 4.63(18) . . . . ?
Cu1 O1 C7 C8 0.3(3) . . . . ?
Cu1 O1 C7 C6 -178.65(14) . . . . ?
Cu1 O2 C9 C8 -4.2(3) . . . . ?
Cu1 O2 C9 C10 175.07(14) . . . . ?
O1 C7 C6 C1 52.2(3) . . . . ?
C8 C7 C6 C1 -126.8(2) . . . . ?
O1 C7 C6 C5 -128.2(2) . . . . ?
C8 C7 C6 C5 52.8(3) . . . . ?
O2 C9 C10 C11 -49.4(3) . . . . ?
C8 C9 C10 C11 129.9(2) . . . . ?
O2 C9 C10 C15 130.9(2) . . . . ?
C8 C9 C10 C15 -49.8(3) . . . . ?
C15 C10 C11 F4 175.47(19) . . . . ?
C9 C10 C11 F4 -4.3(3) . . . . ?
C15 C10 C11 C12 -2.9(3) . . . . ?
C9 C10 C11 C12 177.4(2) . . . . ?
C5 C6 C1 F1 -176.85(19) . . . . ?
C7 C6 C1 F1 2.8(3) . . . . ?
C5 C6 C1 C2 0.8(3) . . . . ?
C7 C6 C1 C2 -179.5(2) . . . . ?
C1 C6 C5 F3 178.77(19) . . . . ?
C7 C6 C5 F3 -0.9(3) . . . . ?
C1 C6 C5 C4 -2.5(3) . . . . ?
C7 C6 C5 C4 177.8(2) . . . . ?
O2 C9 C8 C7 0.4(4) . . . . ?
C10 C9 C8 C7 -178.8(2) . . . . ?
O1 C7 C8 C9 1.8(4) . . . . ?
C6 C7 C8 C9 -179.3(2) . . . . ?
F2 C3 C4 C5 179.4(2) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
F3 C5 C4 C3 -178.9(2) . . . . ?
C6 C5 C4 C3 2.4(4) . . . . ?
F2 C3 C2 C1 179.0(2) . . . . ?
C4 C3 C2 C1 -1.1(4) . . . . ?
F1 C1 C2 C3 178.6(2) . . . . ?
C6 C1 C2 C3 0.9(3) . . . . ?
C13 C14 C15 F6 -179.4(2) . . . . ?
C13 C14 C15 C10 -1.1(4) . . . . ?
C11 C10 C15 F6 -178.6(2) . . . . ?
C9 C10 C15 F6 1.2(3) . . . . ?
C11 C10 C15 C14 3.2(3) . . . . ?
C9 C10 C15 C14 -177.1(2) . . . . ?
F4 C11 C12 C13 -177.8(2) . . . . ?
C10 C11 C12 C13 0.6(3) . . . . ?
C11 C12 C13 F5 -177.5(2) . . . . ?
C11 C12 C13 C14 1.8(4) . . . . ?
C15 C14 C13 F5 177.7(2) . . . . ?
C15 C14 C13 C12 -1.5(4) . . . . ?
C16 C21 C20 C19 0.4(5) . . . . ?
C20 C21 C16 C17 1.5(5) . . . . ?
C17 C18 C19 C20 0.7(6) . . . . ?
C21 C20 C19 C18 -1.6(5) . . . . ?
C19 C18 C17 C16 1.3(6) . . . . ?
C21 C16 C17 C18 -2.4(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.813
_refine_diff_density_min         -0.545
_refine_diff_density_rms         0.070
_database_code_depnum_ccdc_archive 'CCDC 895492'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_110413b5
#TrackingRef 'web_deposit_cif_file_2_AkikoHori_1344479752.110413b5.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H10 Cu F12 O4, 2(C7 H8 O)'
_chemical_formula_sum            'C44 H26 Cu F12 O6'
_chemical_formula_weight         942.20

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.1260(15)
_cell_length_b                   11.308(2)
_cell_length_c                   13.124(3)
_cell_angle_alpha                111.308(2)
_cell_angle_beta                 95.096(2)
_cell_angle_gamma                100.130(2)
_cell_volume                     956.4(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    173
_cell_measurement_reflns_used    6090
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      28.12

_exptl_crystal_description       prismatic
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             475
_exptl_absorpt_coefficient_mu    0.681
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8536
_exptl_absorpt_correction_T_max  0.9350
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            10827
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0280
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.94
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4257
_reflns_number_gt                3929
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0397P)²+0.4476P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4257
_refine_ls_number_parameters     287
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0299
_refine_ls_wR_factor_ref         0.0823
_refine_ls_wR_factor_gt          0.0802
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.5000 1.0000 1.0000 0.02038(8) Uani 1 2 d S . .
O1 O 0.28406(15) 0.88575(11) 0.89105(9) 0.0242(2) Uani 1 1 d . . .
O2 O 0.43290(15) 0.93000(11) 1.10826(9) 0.0250(2) Uani 1 1 d . . .
O3 O 0.2019(2) 0.06763(12) 0.63420(10) 0.0369(3) Uani 1 1 d . . .
C1 C -0.0133(2) 0.68924(15) 0.70831(13) 0.0223(3) Uani 1 1 d . . .
C2 C -0.1638(2) 0.64494(16) 0.62048(13) 0.0260(3) Uani 1 1 d . . .
H2 H -0.1482 0.5966 0.5468 0.031 Uiso 1 1 calc R . .
C3 C -0.3384(2) 0.67460(15) 0.64525(13) 0.0259(3) Uani 1 1 d . . .
C4 C -0.3684(2) 0.74154(16) 0.75100(14) 0.0279(3) Uani 1 1 d . . .
H4 H -0.4903 0.7604 0.7657 0.033 Uiso 1 1 calc R . .
C5 C -0.2120(2) 0.77987(15) 0.83457(13) 0.0247(3) Uani 1 1 d . . .
C6 C -0.0289(2) 0.75772(14) 0.81792(12) 0.0209(3) Uani 1 1 d . . .
C7 C 0.1422(2) 0.81508(15) 0.91028(12) 0.0214(3) Uani 1 1 d . . .
C8 C 0.1338(2) 0.78854(16) 1.00517(13) 0.0252(3) Uani 1 1 d . . .
H8 H 0.0231 0.7295 1.0075 0.030 Uiso 1 1 calc R . .
C9 C 0.2818(2) 0.84522(15) 1.09792(12) 0.0218(3) Uani 1 1 d . . .
C10 C 0.2608(2) 0.80676(15) 1.19488(12) 0.0214(3) Uani 1 1 d . . .
C11 C 0.2965(2) 0.89758(15) 1.30381(13) 0.0251(3) Uani 1 1 d . . .
C12 C 0.2711(2) 0.86648(17) 1.39485(14) 0.0287(3) Uani 1 1 d . . .
H12 H 0.2939 0.9314 1.4679 0.034 Uiso 1 1 calc R . .
C13 C 0.2107(2) 0.73580(18) 1.37390(14) 0.0292(4) Uani 1 1 d . . .
C14 C 0.1774(2) 0.63918(16) 1.26992(14) 0.0285(3) Uani 1 1 d . . .
H14 H 0.1391 0.5499 1.2585 0.034 Uiso 1 1 calc R . .
C15 C 0.2022(2) 0.67760(15) 1.18279(13) 0.0245(3) Uani 1 1 d . . .
C16 C 0.2870(3) 0.28105(18) 0.64560(16) 0.0333(4) Uani 1 1 d . . .
H16 H 0.2782 0.2471 0.5672 0.040 Uiso 1 1 calc R . .
C17 C 0.3360(3) 0.41400(19) 0.70532(19) 0.0422(5) Uani 1 1 d . . .
H17 H 0.3610 0.4714 0.6678 0.051 Uiso 1 1 calc R . .
C18 C 0.3488(3) 0.4641(2) 0.8196(2) 0.0481(5) Uani 1 1 d . . .
H18 H 0.3810 0.5556 0.8604 0.058 Uiso 1 1 calc R . .
C19 C 0.3146(3) 0.3805(2) 0.87360(17) 0.0423(5) Uani 1 1 d . . .
H19 H 0.3248 0.4152 0.9521 0.051 Uiso 1 1 calc R . .
C20 C 0.2652(2) 0.24588(18) 0.81537(14) 0.0325(4) Uani 1 1 d . . .
H20 H 0.2421 0.1889 0.8534 0.039 Uiso 1 1 calc R . .
C21 C 0.2505(2) 0.19676(16) 0.70056(14) 0.0271(3) Uani 1 1 d . . .
C22 C 0.1531(3) -0.02275(18) 0.68574(17) 0.0405(4) Uani 1 1 d . . .
H22A H 0.2661 -0.0173 0.7369 0.061 Uiso 1 1 calc R . .
H22B H 0.1125 -0.1113 0.6288 0.061 Uiso 1 1 calc R . .
H22C H 0.0472 -0.0016 0.7269 0.061 Uiso 1 1 calc R . .
F1 F 0.16998(16) 0.58350(9) 1.08038(8) 0.0360(2) Uani 1 1 d . . .
F2 F 0.15918(14) 0.66215(10) 0.68609(8) 0.0334(2) Uani 1 1 d . . .
F3 F 0.18231(17) 0.70089(11) 1.46048(9) 0.0426(3) Uani 1 1 d . . .
F4 F 0.35141(17) 1.02511(9) 1.32240(8) 0.0377(3) Uani 1 1 d . . .
F5 F -0.48738(15) 0.63696(11) 0.56122(9) 0.0385(3) Uani 1 1 d . . .
F6 F -0.23761(15) 0.84719(11) 0.93942(8) 0.0379(3) Uani 1 1 d . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.9102(11) . ?
Cu1 O1 1.9102(11) 2_677 ?
Cu1 O2 1.9180(11) 2_677 ?
Cu1 O2 1.9180(11) . ?
O1 C7 1.2775(18) . ?
O2 C9 1.2700(19) . ?
O3 C21 1.362(2) . ?
O3 C22 1.429(2) . ?
C1 F2 1.3495(17) . ?
C1 C2 1.379(2) . ?
C1 C6 1.389(2) . ?
C2 C3 1.380(2) . ?
C2 H2 0.9500 . ?
C3 F5 1.3477(18) . ?
C3 C4 1.375(2) . ?
C4 C5 1.378(2) . ?
C4 H4 0.9500 . ?
C5 F6 1.3559(18) . ?
C5 C6 1.392(2) . ?
C6 C7 1.505(2) . ?
C7 C8 1.387(2) . ?
C8 C9 1.405(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.498(2) . ?
C10 C15 1.392(2) . ?
C10 C11 1.393(2) . ?
C11 F4 1.3495(19) . ?
C11 C12 1.380(2) . ?
C12 C13 1.380(2) . ?
C12 H12 0.9500 . ?
C13 F3 1.3515(18) . ?
C13 C14 1.371(2) . ?
C14 C15 1.377(2) . ?
C14 H14 0.9500 . ?
C15 F1 1.3459(18) . ?
C16 C17 1.381(3) . ?
C16 C21 1.394(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.385(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.375(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.394(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.390(2) . ?
C20 H20 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 180.0 . 2_677 ?
O1 Cu1 O2 86.77(5) . 2_677 ?
O1 Cu1 O2 93.23(5) 2_677 2_677 ?
O1 Cu1 O2 93.23(5) . . ?
O1 Cu1 O2 86.77(5) 2_677 . ?
O2 Cu1 O2 179.999(1) 2_677 . ?
C7 O1 Cu1 124.73(10) . . ?
C9 O2 Cu1 126.14(10) . . ?
C21 O3 C22 117.59(14) . . ?
F2 C1 C2 117.58(14) . . ?
F2 C1 C6 118.14(13) . . ?
C2 C1 C6 124.27(14) . . ?
C1 C2 C3 116.47(15) . . ?
C1 C2 H2 121.8 . . ?
C3 C2 H2 121.8 . . ?
F5 C3 C4 118.08(14) . . ?
F5 C3 C2 118.33(15) . . ?
C4 C3 C2 123.59(15) . . ?
C3 C4 C5 116.41(15) . . ?
C3 C4 H4 121.8 . . ?
C5 C4 H4 121.8 . . ?
F6 C5 C4 117.47(14) . . ?
F6 C5 C6 118.10(14) . . ?
C4 C5 C6 124.39(15) . . ?
C1 C6 C5 114.83(14) . . ?
C1 C6 C7 122.81(13) . . ?
C5 C6 C7 122.10(14) . . ?
O1 C7 C8 126.57(14) . . ?
O1 C7 C6 114.07(13) . . ?
C8 C7 C6 119.35(13) . . ?
C7 C8 C9 122.80(14) . . ?
C7 C8 H8 118.6 . . ?
C9 C8 H8 118.6 . . ?
O2 C9 C8 125.32(14) . . ?
O2 C9 C10 116.19(13) . . ?
C8 C9 C10 118.47(13) . . ?
C15 C10 C11 114.94(14) . . ?
C15 C10 C9 122.51(14) . . ?
C11 C10 C9 122.54(14) . . ?
F4 C11 C12 117.11(14) . . ?
F4 C11 C10 118.57(14) . . ?
C12 C11 C10 124.25(15) . . ?
C13 C12 C11 116.27(15) . . ?
C13 C12 H12 121.9 . . ?
C11 C12 H12 121.9 . . ?
F3 C13 C14 118.07(16) . . ?
F3 C13 C12 118.31(15) . . ?
C14 C13 C12 123.62(15) . . ?
C13 C14 C15 116.90(15) . . ?
C13 C14 H14 121.5 . . ?
C15 C14 H14 121.5 . . ?
F1 C15 C14 117.38(14) . . ?
F1 C15 C10 118.65(14) . . ?
C14 C15 C10 123.97(15) . . ?
C17 C16 C21 119.86(18) . . ?
C17 C16 H16 120.1 . . ?
C21 C16 H16 120.1 . . ?
C16 C17 C18 120.35(19) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 119.60(18) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C18 C19 C20 121.25(19) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C21 C20 C19 118.65(18) . . ?
C21 C20 H20 120.7 . . ?
C19 C20 H20 120.7 . . ?
O3 C21 C20 124.38(16) . . ?
O3 C21 C16 115.33(15) . . ?
C20 C21 C16 120.29(16) . . ?
O3 C22 H22A 109.5 . . ?
O3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 Cu1 O1 C7 -101(9) 2_677 . . . ?
O2 Cu1 O1 C7 -168.35(13) 2_677 . . . ?
O2 Cu1 O1 C7 11.65(13) . . . . ?
O1 Cu1 O2 C9 -5.00(13) . . . . ?
O1 Cu1 O2 C9 174.99(13) 2_677 . . . ?
O2 Cu1 O2 C9 117(9) 2_677 . . . ?
F2 C1 C2 C3 -179.60(13) . . . . ?
C6 C1 C2 C3 1.5(2) . . . . ?
C1 C2 C3 F5 177.76(14) . . . . ?
C1 C2 C3 C4 -1.7(2) . . . . ?
F5 C3 C4 C5 -179.19(14) . . . . ?
C2 C3 C4 C5 0.2(2) . . . . ?
C3 C4 C5 F6 179.34(14) . . . . ?
C3 C4 C5 C6 1.5(2) . . . . ?
F2 C1 C6 C5 -178.85(13) . . . . ?
C2 C1 C6 C5 0.0(2) . . . . ?
F2 C1 C6 C7 6.8(2) . . . . ?
C2 C1 C6 C7 -174.32(14) . . . . ?
F6 C5 C6 C1 -179.42(13) . . . . ?
C4 C5 C6 C1 -1.6(2) . . . . ?
F6 C5 C6 C7 -5.1(2) . . . . ?
C4 C5 C6 C7 172.75(15) . . . . ?
Cu1 O1 C7 C8 -13.0(2) . . . . ?
Cu1 O1 C7 C6 166.83(10) . . . . ?
C1 C6 C7 O1 51.4(2) . . . . ?
C5 C6 C7 O1 -122.48(16) . . . . ?
C1 C6 C7 C8 -128.71(16) . . . . ?
C5 C6 C7 C8 57.4(2) . . . . ?
O1 C7 C8 C9 4.2(3) . . . . ?
C6 C7 C8 C9 -175.60(14) . . . . ?
Cu1 O2 C9 C8 -1.1(2) . . . . ?
Cu1 O2 C9 C10 -179.46(10) . . . . ?
C7 C8 C9 O2 3.5(3) . . . . ?
C7 C8 C9 C10 -178.18(15) . . . . ?
O2 C9 C10 C15 -135.72(16) . . . . ?
C8 C9 C10 C15 45.8(2) . . . . ?
O2 C9 C10 C11 45.0(2) . . . . ?
C8 C9 C10 C11 -133.45(16) . . . . ?
C15 C10 C11 F4 -179.10(14) . . . . ?
C9 C10 C11 F4 0.2(2) . . . . ?
C15 C10 C11 C12 -2.1(2) . . . . ?
C9 C10 C11 C12 177.20(15) . . . . ?
F4 C11 C12 C13 178.58(15) . . . . ?
C10 C11 C12 C13 1.6(3) . . . . ?
C11 C12 C13 F3 -179.43(15) . . . . ?
C11 C12 C13 C14 0.4(3) . . . . ?
F3 C13 C14 C15 178.22(14) . . . . ?
C12 C13 C14 C15 -1.6(3) . . . . ?
C13 C14 C15 F1 179.96(15) . . . . ?
C13 C14 C15 C10 1.0(2) . . . . ?
C11 C10 C15 F1 -178.17(14) . . . . ?
C9 C10 C15 F1 2.5(2) . . . . ?
C11 C10 C15 C14 0.8(2) . . . . ?
C9 C10 C15 C14 -178.54(15) . . . . ?
C21 C16 C17 C18 -0.1(3) . . . . ?
C16 C17 C18 C19 0.7(3) . . . . ?
C17 C18 C19 C20 -0.6(3) . . . . ?
C18 C19 C20 C21 -0.1(3) . . . . ?
C22 O3 C21 C20 3.4(3) . . . . ?
C22 O3 C21 C16 -176.78(16) . . . . ?
C19 C20 C21 O3 -179.43(16) . . . . ?
C19 C20 C21 C16 0.8(3) . . . . ?
C17 C16 C21 O3 179.52(16) . . . . ?
C17 C16 C21 C20 -0.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.052
_database_code_depnum_ccdc_archive 'CCDC 895493'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_111108b2
#TrackingRef 'web_deposit_cif_file_3_AkikoHori_1344479752.111108b2.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H10 Cu F12 O4, C8 H10'
_chemical_formula_sum            'C38 H20 Cu F12 O4'
_chemical_formula_weight         832.09

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   7.4012(5)
_cell_length_b                   25.6642(16)
_cell_length_c                   17.3466(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.9960(10)
_cell_angle_gamma                90.00
_cell_volume                     3286.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    7081
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      26.30

_exptl_crystal_description       prismatic
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.681
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1668
_exptl_absorpt_coefficient_mu    0.776
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8296
_exptl_absorpt_correction_T_max  0.9405
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            36824
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_av_sigmaI/netI    0.0425
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.35
_diffrn_reflns_theta_max         27.48
_reflns_number_total             7517
_reflns_number_gt                5684
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0531P)²+1.0867P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7517
_refine_ls_number_parameters     498
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.1057
_refine_ls_wR_factor_gt          0.0902
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.87721(4) 0.767843(11) 0.064456(16) 0.01426(9) Uani 1 1 d . . .
O1 O 0.8070(2) 0.72788(6) 0.15052(9) 0.0165(3) Uani 1 1 d . . .
O2 O 0.7042(2) 0.82116(6) 0.07949(9) 0.0176(4) Uani 1 1 d . . .
O3 O 0.9415(2) 0.80670(6) -0.02422(9) 0.0170(3) Uani 1 1 d . . .
O4 O 1.0501(2) 0.71412(6) 0.05033(9) 0.0178(4) Uani 1 1 d . . .
C1 C 0.6616(3) 0.64437(9) 0.24108(13) 0.0173(5) Uani 1 1 d . . .
C2 C 0.6377(3) 0.60746(9) 0.29703(14) 0.0195(5) Uani 1 1 d . . .
H2 H 0.6525 0.5714 0.2872 0.023 Uiso 1 1 calc R . .
C3 C 0.5914(3) 0.62530(9) 0.36796(14) 0.0197(5) Uani 1 1 d . . .
C4 C 0.5709(3) 0.67715(9) 0.38439(13) 0.0176(5) Uani 1 1 d . . .
H4 H 0.5412 0.6885 0.4341 0.021 Uiso 1 1 calc R . .
C5 C 0.5954(3) 0.71194(9) 0.32571(14) 0.0160(5) Uani 1 1 d . . .
C6 C 0.6403(3) 0.69802(9) 0.25192(13) 0.0144(5) Uani 1 1 d . . .
C7 C 0.6706(3) 0.73695(9) 0.18953(13) 0.0144(5) Uani 1 1 d . . .
C8 C 0.5505(3) 0.77881(9) 0.17805(13) 0.0160(5) Uani 1 1 d . . .
H8 H 0.4476 0.7803 0.2078 0.019 Uiso 1 1 calc R . .
C9 C 0.5756(3) 0.81851(9) 0.12480(13) 0.0146(5) Uani 1 1 d . . .
C10 C 0.4483(3) 0.86383(9) 0.11927(13) 0.0166(5) Uani 1 1 d . . .
C11 C 0.5082(3) 0.91478(10) 0.11055(15) 0.0212(5) Uani 1 1 d . . .
C12 C 0.3954(4) 0.95733(10) 0.10333(15) 0.0259(6) Uani 1 1 d . . .
H12 H 0.4420 0.9915 0.0972 0.031 Uiso 1 1 calc R . .
C13 C 0.2127(4) 0.94855(10) 0.10539(15) 0.0256(6) Uani 1 1 d . . .
C14 C 0.1392(4) 0.89974(10) 0.11383(14) 0.0234(6) Uani 1 1 d . . .
H14 H 0.0123 0.8944 0.1146 0.028 Uiso 1 1 calc R . .
C15 C 0.2605(3) 0.85909(9) 0.12117(13) 0.0181(5) Uani 1 1 d . . .
C16 C 1.0879(3) 0.88462(9) -0.12740(13) 0.0186(5) Uani 1 1 d . . .
C17 C 1.1085(3) 0.91873(9) -0.18754(14) 0.0201(5) Uani 1 1 d . . .
H17 H 1.1086 0.9554 -0.1800 0.024 Uiso 1 1 calc R . .
C18 C 1.1289(3) 0.89726(9) -0.25884(13) 0.0175(5) Uani 1 1 d . . .
C19 C 1.1320(3) 0.84456(9) -0.27227(14) 0.0173(5) Uani 1 1 d . . .
H19 H 1.1458 0.8308 -0.3224 0.021 Uiso 1 1 calc R . .
C20 C 1.1140(3) 0.81271(9) -0.20946(13) 0.0156(5) Uani 1 1 d . . .
C21 C 1.0908(3) 0.83058(9) -0.13497(13) 0.0141(5) Uani 1 1 d . . .
C22 C 1.0679(3) 0.79489(9) -0.06759(13) 0.0147(5) Uani 1 1 d . . .
C23 C 1.1836(3) 0.75227(9) -0.05725(13) 0.0158(5) Uani 1 1 d . . .
H23 H 1.2776 0.7484 -0.0914 0.019 Uiso 1 1 calc R . .
C24 C 1.1689(3) 0.71504(9) 0.00041(13) 0.0144(5) Uani 1 1 d . . .
C25 C 1.3003(3) 0.67074(9) 0.00491(13) 0.0151(5) Uani 1 1 d . . .
C26 C 1.2427(3) 0.61915(9) 0.00943(13) 0.0175(5) Uani 1 1 d . . .
C27 C 1.3592(3) 0.57698(9) 0.01232(14) 0.0212(5) Uani 1 1 d . . .
H27 H 1.3159 0.5422 0.0152 0.025 Uiso 1 1 calc R . .
C28 C 1.5404(4) 0.58779(9) 0.01089(14) 0.0219(5) Uani 1 1 d . . .
C29 C 1.6107(3) 0.63745(9) 0.00654(13) 0.0176(5) Uani 1 1 d . . .
H29 H 1.7371 0.6436 0.0056 0.021 Uiso 1 1 calc R . .
C30 C 1.4867(3) 0.67735(9) 0.00370(13) 0.0152(5) Uani 1 1 d . . .
C31 C 0.0617(4) 0.61005(11) 0.81500(16) 0.0281(6) Uani 1 1 d . . .
C32 C 0.0476(4) 0.55600(11) 0.82001(18) 0.0334(7) Uani 1 1 d . . .
H32 H -0.0684 0.5405 0.8227 0.040 Uiso 1 1 calc R . .
C33 C 0.1992(4) 0.52459(11) 0.82110(16) 0.0294(6) Uani 1 1 d . . .
H33 H 0.1856 0.4879 0.8254 0.035 Uiso 1 1 calc R . .
C34 C 0.3703(3) 0.54534(10) 0.81609(14) 0.0245(6) Uani 1 1 d . . .
C35 C 0.3836(4) 0.59963(10) 0.81072(14) 0.0250(6) Uani 1 1 d . . .
H35 H 0.4993 0.6151 0.8071 0.030 Uiso 1 1 calc R . .
C36 C 0.2330(4) 0.63094(10) 0.81053(14) 0.0232(5) Uani 1 1 d . . .
H36 H 0.2468 0.6677 0.8073 0.028 Uiso 1 1 calc R . .
C37 C -0.1031(4) 0.64453(13) 0.8134(2) 0.0456(8) Uani 1 1 d . . .
H37A H -0.0652 0.6811 0.8155 0.068 Uiso 1 1 calc R . .
H37B H -0.1727 0.6366 0.8579 0.068 Uiso 1 1 calc R . .
H37C H -0.1785 0.6383 0.7656 0.068 Uiso 1 1 calc R . .
C38 C 0.5355(4) 0.51150(12) 0.81732(17) 0.0337(7) Uani 1 1 d . . .
H38A H 0.5024 0.4755 0.8291 0.051 Uiso 1 1 calc R . .
H38B H 0.6257 0.5241 0.8570 0.051 Uiso 1 1 calc R . .
H38C H 0.5863 0.5127 0.7667 0.051 Uiso 1 1 calc R . .
F1 F 0.7046(2) 0.62679(5) 0.17155(8) 0.0250(3) Uani 1 1 d . . .
F2 F 0.5663(2) 0.59012(6) 0.42395(8) 0.0306(4) Uani 1 1 d . . .
F3 F 0.5786(2) 0.76327(5) 0.34182(8) 0.0228(3) Uani 1 1 d . . .
F4 F 0.6882(2) 0.92375(6) 0.11214(10) 0.0306(4) Uani 1 1 d . . .
F5 F 0.1000(2) 0.98966(6) 0.09822(10) 0.0382(4) Uani 1 1 d . . .
F6 F 0.18952(18) 0.81071(6) 0.12940(8) 0.0242(3) Uani 1 1 d . . .
F7 F 1.0692(2) 0.90521(6) -0.05723(8) 0.0315(4) Uani 1 1 d . . .
F8 F 1.1442(2) 0.92980(5) -0.31930(8) 0.0266(3) Uani 1 1 d . . .
F9 F 1.1171(2) 0.76082(5) -0.22182(8) 0.0253(3) Uani 1 1 d . . .
F10 F 1.06439(19) 0.60942(5) 0.00871(9) 0.0247(3) Uani 1 1 d . . .
F11 F 1.6586(2) 0.54755(6) 0.01474(10) 0.0336(4) Uani 1 1 d . . .
F12 F 1.55247(18) 0.72665(5) 0.00215(8) 0.0183(3) Uani 1 1 d . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O2 1.9046(16) . ?
Cu1 O4 1.9086(16) . ?
Cu1 O1 1.9129(16) . ?
Cu1 O3 1.9208(16) . ?
O1 C7 1.275(3) . ?
O2 C9 1.277(3) . ?
O3 C22 1.277(3) . ?
O4 C24 1.276(3) . ?
C1 F1 1.346(3) . ?
C1 C2 1.376(3) . ?
C1 C6 1.400(3) . ?
C2 C3 1.378(3) . ?
C2 H2 0.9500 . ?
C3 F2 1.349(3) . ?
C3 C4 1.372(3) . ?
C4 C5 1.375(3) . ?
C4 H4 0.9500 . ?
C5 F3 1.354(3) . ?
C5 C6 1.391(3) . ?
C6 C7 1.501(3) . ?
C7 C8 1.400(3) . ?
C8 C9 1.396(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.496(3) . ?
C10 C11 1.392(3) . ?
C10 C15 1.398(3) . ?
C11 F4 1.350(3) . ?
C11 C12 1.375(3) . ?
C12 C13 1.374(4) . ?
C12 H12 0.9500 . ?
C13 F5 1.345(3) . ?
C13 C14 1.378(4) . ?
C14 C15 1.377(3) . ?
C14 H14 0.9500 . ?
C15 F6 1.360(3) . ?
C16 F7 1.343(3) . ?
C16 C17 1.378(3) . ?
C16 C21 1.393(3) . ?
C17 C18 1.372(3) . ?
C17 H17 0.9500 . ?
C18 F8 1.352(3) . ?
C18 C19 1.373(3) . ?
C19 C20 1.376(3) . ?
C19 H19 0.9500 . ?
C20 F9 1.349(3) . ?
C20 C21 1.393(3) . ?
C21 C22 1.504(3) . ?
C22 C23 1.393(3) . ?
C23 C24 1.393(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.495(3) . ?
C25 C30 1.391(3) . ?
C25 C26 1.395(3) . ?
C26 F10 1.343(3) . ?
C26 C27 1.382(3) . ?
C27 C28 1.371(4) . ?
C27 H27 0.9500 . ?
C28 F11 1.352(3) . ?
C28 C29 1.381(3) . ?
C29 C30 1.374(3) . ?
C29 H29 0.9500 . ?
C30 F12 1.357(3) . ?
C31 C36 1.384(4) . ?
C31 C32 1.394(4) . ?
C31 C37 1.505(4) . ?
C32 C33 1.381(4) . ?
C32 H32 0.9500 . ?
C33 C34 1.383(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.400(4) . ?
C34 C38 1.498(4) . ?
C35 C36 1.374(4) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 O4 179.44(7) . . ?
O2 Cu1 O1 93.24(7) . . ?
O4 Cu1 O1 86.21(7) . . ?
O2 Cu1 O3 86.75(7) . . ?
O4 Cu1 O3 93.80(7) . . ?
O1 Cu1 O3 178.01(7) . . ?
C7 O1 Cu1 125.76(15) . . ?
C9 O2 Cu1 125.65(15) . . ?
C22 O3 Cu1 125.54(15) . . ?
C24 O4 Cu1 124.98(15) . . ?
F1 C1 C2 116.8(2) . . ?
F1 C1 C6 119.1(2) . . ?
C2 C1 C6 124.1(2) . . ?
C1 C2 C3 116.9(2) . . ?
C1 C2 H2 121.5 . . ?
C3 C2 H2 121.5 . . ?
F2 C3 C4 118.5(2) . . ?
F2 C3 C2 118.4(2) . . ?
C4 C3 C2 123.1(2) . . ?
C3 C4 C5 117.0(2) . . ?
C3 C4 H4 121.5 . . ?
C5 C4 H4 121.5 . . ?
F3 C5 C4 117.4(2) . . ?
F3 C5 C6 118.1(2) . . ?
C4 C5 C6 124.5(2) . . ?
C5 C6 C1 114.4(2) . . ?
C5 C6 C7 123.3(2) . . ?
C1 C6 C7 122.3(2) . . ?
O1 C7 C8 125.7(2) . . ?
O1 C7 C6 115.1(2) . . ?
C8 C7 C6 119.2(2) . . ?
C9 C8 C7 122.8(2) . . ?
C9 C8 H8 118.6 . . ?
C7 C8 H8 118.6 . . ?
O2 C9 C8 125.8(2) . . ?
O2 C9 C10 114.3(2) . . ?
C8 C9 C10 119.8(2) . . ?
C11 C10 C15 114.2(2) . . ?
C11 C10 C9 122.2(2) . . ?
C15 C10 C9 123.6(2) . . ?
F4 C11 C12 117.3(2) . . ?
F4 C11 C10 118.6(2) . . ?
C12 C11 C10 124.0(2) . . ?
C13 C12 C11 117.4(2) . . ?
C13 C12 H12 121.3 . . ?
C11 C12 H12 121.3 . . ?
F5 C13 C12 118.3(2) . . ?
F5 C13 C14 118.4(2) . . ?
C12 C13 C14 123.3(2) . . ?
C15 C14 C13 116.0(2) . . ?
C15 C14 H14 122.0 . . ?
C13 C14 H14 122.0 . . ?
F6 C15 C14 116.6(2) . . ?
F6 C15 C10 118.3(2) . . ?
C14 C15 C10 125.1(2) . . ?
F7 C16 C17 117.4(2) . . ?
F7 C16 C21 118.7(2) . . ?
C17 C16 C21 123.9(2) . . ?
C18 C17 C16 116.9(2) . . ?
C18 C17 H17 121.6 . . ?
C16 C17 H17 121.6 . . ?
F8 C18 C17 118.1(2) . . ?
F8 C18 C19 118.3(2) . . ?
C17 C18 C19 123.6(2) . . ?
C18 C19 C20 116.6(2) . . ?
C18 C19 H19 121.7 . . ?
C20 C19 H19 121.7 . . ?
F9 C20 C19 117.2(2) . . ?
F9 C20 C21 118.5(2) . . ?
C19 C20 C21 124.3(2) . . ?
C20 C21 C16 114.8(2) . . ?
C20 C21 C22 123.2(2) . . ?
C16 C21 C22 122.0(2) . . ?
O3 C22 C23 125.4(2) . . ?
O3 C22 C21 116.1(2) . . ?
C23 C22 C21 118.5(2) . . ?
C24 C23 C22 123.6(2) . . ?
C24 C23 H23 118.2 . . ?
C22 C23 H23 118.2 . . ?
O4 C24 C23 126.3(2) . . ?
O4 C24 C25 115.3(2) . . ?
C23 C24 C25 118.4(2) . . ?
C30 C25 C26 115.1(2) . . ?
C30 C25 C24 123.3(2) . . ?
C26 C25 C24 121.6(2) . . ?
F10 C26 C27 117.7(2) . . ?
F10 C26 C25 118.7(2) . . ?
C27 C26 C25 123.6(2) . . ?
C28 C27 C26 116.7(2) . . ?
C28 C27 H27 121.7 . . ?
C26 C27 H27 121.7 . . ?
F11 C28 C27 118.4(2) . . ?
F11 C28 C29 117.5(2) . . ?
C27 C28 C29 124.1(2) . . ?
C30 C29 C28 115.9(2) . . ?
C30 C29 H29 122.1 . . ?
C28 C29 H29 122.1 . . ?
F12 C30 C29 117.1(2) . . ?
F12 C30 C25 118.1(2) . . ?
C29 C30 C25 124.7(2) . . ?
C36 C31 C32 117.5(3) . . ?
C36 C31 C37 121.0(3) . . ?
C32 C31 C37 121.5(3) . . ?
C33 C32 C31 121.1(3) . . ?
C33 C32 H32 119.4 . . ?
C31 C32 H32 119.4 . . ?
C32 C33 C34 121.4(3) . . ?
C32 C33 H33 119.3 . . ?
C34 C33 H33 119.3 . . ?
C33 C34 C35 117.1(2) . . ?
C33 C34 C38 121.7(2) . . ?
C35 C34 C38 121.1(2) . . ?
C36 C35 C34 121.4(2) . . ?
C36 C35 H35 119.3 . . ?
C34 C35 H35 119.3 . . ?
C35 C36 C31 121.3(2) . . ?
C35 C36 H36 119.3 . . ?
C31 C36 H36 119.3 . . ?
C31 C37 H37A 109.5 . . ?
C31 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C31 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C34 C38 H38A 109.5 . . ?
C34 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C34 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 Cu1 O1 C7 8.37(19) . . . . ?
O4 Cu1 O1 C7 -171.73(19) . . . . ?
O3 Cu1 O1 C7 -81(2) . . . . ?
O4 Cu1 O2 C9 -21(8) . . . . ?
O1 Cu1 O2 C9 -11.08(19) . . . . ?
O3 Cu1 O2 C9 166.93(19) . . . . ?
O2 Cu1 O3 C22 176.97(19) . . . . ?
O4 Cu1 O3 C22 -2.95(19) . . . . ?
O1 Cu1 O3 C22 -93.3(19) . . . . ?
O2 Cu1 O4 C24 -166(28) . . . . ?
O1 Cu1 O4 C24 -175.28(19) . . . . ?
O3 Cu1 O4 C24 6.71(19) . . . . ?
F1 C1 C2 C3 -179.2(2) . . . . ?
C6 C1 C2 C3 -0.6(4) . . . . ?
C1 C2 C3 F2 179.7(2) . . . . ?
C1 C2 C3 C4 -0.7(4) . . . . ?
F2 C3 C4 C5 -179.2(2) . . . . ?
C2 C3 C4 C5 1.2(4) . . . . ?
C3 C4 C5 F3 -178.8(2) . . . . ?
C3 C4 C5 C6 -0.5(4) . . . . ?
F3 C5 C6 C1 177.7(2) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
F3 C5 C6 C7 -0.1(3) . . . . ?
C4 C5 C6 C7 -178.4(2) . . . . ?
F1 C1 C6 C5 179.8(2) . . . . ?
C2 C1 C6 C5 1.2(4) . . . . ?
F1 C1 C6 C7 -2.4(3) . . . . ?
C2 C1 C6 C7 179.0(2) . . . . ?
Cu1 O1 C7 C8 -2.2(3) . . . . ?
Cu1 O1 C7 C6 177.09(14) . . . . ?
C5 C6 C7 O1 136.7(2) . . . . ?
C1 C6 C7 O1 -41.0(3) . . . . ?
C5 C6 C7 C8 -44.0(3) . . . . ?
C1 C6 C7 C8 138.4(2) . . . . ?
O1 C7 C8 C9 -5.0(4) . . . . ?
C6 C7 C8 C9 175.7(2) . . . . ?
Cu1 O2 C9 C8 7.9(3) . . . . ?
Cu1 O2 C9 C10 -174.02(14) . . . . ?
C7 C8 C9 O2 2.0(4) . . . . ?
C7 C8 C9 C10 -176.0(2) . . . . ?
O2 C9 C10 C11 -39.7(3) . . . . ?
C8 C9 C10 C11 138.5(2) . . . . ?
O2 C9 C10 C15 139.3(2) . . . . ?
C8 C9 C10 C15 -42.4(3) . . . . ?
C15 C10 C11 F4 176.6(2) . . . . ?
C9 C10 C11 F4 -4.3(4) . . . . ?
C15 C10 C11 C12 -0.8(4) . . . . ?
C9 C10 C11 C12 178.3(2) . . . . ?
F4 C11 C12 C13 -177.0(2) . . . . ?
C10 C11 C12 C13 0.4(4) . . . . ?
C11 C12 C13 F5 -179.8(2) . . . . ?
C11 C12 C13 C14 -0.3(4) . . . . ?
F5 C13 C14 C15 -179.8(2) . . . . ?
C12 C13 C14 C15 0.7(4) . . . . ?
C13 C14 C15 F6 -179.9(2) . . . . ?
C13 C14 C15 C10 -1.2(4) . . . . ?
C11 C10 C15 F6 179.9(2) . . . . ?
C9 C10 C15 F6 0.8(3) . . . . ?
C11 C10 C15 C14 1.2(4) . . . . ?
C9 C10 C15 C14 -177.9(2) . . . . ?
F7 C16 C17 C18 179.5(2) . . . . ?
C21 C16 C17 C18 1.5(4) . . . . ?
C16 C17 C18 F8 178.1(2) . . . . ?
C16 C17 C18 C19 -0.9(4) . . . . ?
F8 C18 C19 C20 -179.3(2) . . . . ?
C17 C18 C19 C20 -0.3(4) . . . . ?
C18 C19 C20 F9 -179.9(2) . . . . ?
C18 C19 C20 C21 1.0(4) . . . . ?
F9 C20 C21 C16 -179.6(2) . . . . ?
C19 C20 C21 C16 -0.4(3) . . . . ?
F9 C20 C21 C22 -0.3(3) . . . . ?
C19 C20 C21 C22 178.8(2) . . . . ?
F7 C16 C21 C20 -178.8(2) . . . . ?
C17 C16 C21 C20 -0.8(4) . . . . ?
F7 C16 C21 C22 1.9(3) . . . . ?
C17 C16 C21 C22 179.9(2) . . . . ?
Cu1 O3 C22 C23 -1.3(3) . . . . ?
Cu1 O3 C22 C21 178.66(14) . . . . ?
C20 C21 C22 O3 -134.5(2) . . . . ?
C16 C21 C22 O3 44.7(3) . . . . ?
C20 C21 C22 C23 45.5(3) . . . . ?
C16 C21 C22 C23 -135.3(2) . . . . ?
O3 C22 C23 C24 3.7(4) . . . . ?
C21 C22 C23 C24 -176.3(2) . . . . ?
Cu1 O4 C24 C23 -6.6(3) . . . . ?
Cu1 O4 C24 C25 174.72(15) . . . . ?
C22 C23 C24 O4 0.7(4) . . . . ?
C22 C23 C24 C25 179.3(2) . . . . ?
O4 C24 C25 C30 -132.3(2) . . . . ?
C23 C24 C25 C30 49.0(3) . . . . ?
O4 C24 C25 C26 48.8(3) . . . . ?
C23 C24 C25 C26 -130.0(2) . . . . ?
C30 C25 C26 F10 -178.19(19) . . . . ?
C24 C25 C26 F10 0.8(3) . . . . ?
C30 C25 C26 C27 -0.2(3) . . . . ?
C24 C25 C26 C27 178.8(2) . . . . ?
F10 C26 C27 C28 178.3(2) . . . . ?
C25 C26 C27 C28 0.3(4) . . . . ?
C26 C27 C28 F11 179.1(2) . . . . ?
C26 C27 C28 C29 -0.2(4) . . . . ?
F11 C28 C29 C30 -179.2(2) . . . . ?
C27 C28 C29 C30 0.1(4) . . . . ?
C28 C29 C30 F12 177.7(2) . . . . ?
C28 C29 C30 C25 0.0(4) . . . . ?
C26 C25 C30 F12 -177.67(19) . . . . ?
C24 C25 C30 F12 3.3(3) . . . . ?
C26 C25 C30 C29 0.1(3) . . . . ?
C24 C25 C30 C29 -179.0(2) . . . . ?
C36 C31 C32 C33 0.5(4) . . . . ?
C37 C31 C32 C33 179.7(3) . . . . ?
C31 C32 C33 C34 -1.0(4) . . . . ?
C32 C33 C34 C35 0.7(4) . . . . ?
C32 C33 C34 C38 179.9(3) . . . . ?
C33 C34 C35 C36 0.1(4) . . . . ?
C38 C34 C35 C36 -179.2(2) . . . . ?
C34 C35 C36 C31 -0.5(4) . . . . ?
C32 C31 C36 C35 0.2(4) . . . . ?
C37 C31 C36 C35 -178.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.078
_database_code_depnum_ccdc_archive 'CCDC 895494'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_110411a1
#TrackingRef 'web_deposit_cif_file_4_AkikoHori_1344479752.110411a1.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H10 Cu F12 O4, 2(C9 H12)'
_chemical_formula_sum            'C48 H34 Cu F12 O4'
_chemical_formula_weight         966.30

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.0546(11)
_cell_length_b                   9.8563(15)
_cell_length_c                   16.396(3)
_cell_angle_alpha                73.042(2)
_cell_angle_beta                 88.210(2)
_cell_angle_gamma                71.792(2)
_cell_volume                     1033.6(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    100
_cell_measurement_reflns_used    6206
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      27.87

_exptl_crystal_description       prismatic
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             491
_exptl_absorpt_coefficient_mu    0.629
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7870
_exptl_absorpt_correction_T_max  0.9514
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            11627
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0241
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4610
_reflns_number_gt                4170
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0372P)²+0.5062P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4610
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0286
_refine_ls_wR_factor_ref         0.0763
_refine_ls_wR_factor_gt          0.0734
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.5000 0.5000 0.5000 0.01316(8) Uani 1 2 d S . .
O1 O 0.61194(15) 0.63240(11) 0.53326(6) 0.0156(2) Uani 1 1 d . . .
O2 O 0.55195(15) 0.56942(12) 0.38218(6) 0.0169(2) Uani 1 1 d . . .
C1 C 0.7217(2) 0.86816(16) 0.58087(9) 0.0156(3) Uani 1 1 d . . .
C2 C 0.8166(2) 0.93033(17) 0.62546(10) 0.0178(3) Uani 1 1 d . . .
H2 H 0.7451 0.9923 0.6584 0.021 Uiso 1 1 calc R . .
C3 C 1.0208(2) 0.89784(17) 0.61964(9) 0.0171(3) Uani 1 1 d . . .
C4 C 1.1292(2) 0.81211(16) 0.57061(10) 0.0170(3) Uani 1 1 d . . .
H4 H 1.2696 0.7917 0.5676 0.020 Uiso 1 1 calc R . .
C5 C 1.0229(2) 0.75776(16) 0.52639(9) 0.0151(3) Uani 1 1 d . . .
C6 C 0.8180(2) 0.77974(16) 0.53004(9) 0.0144(3) Uani 1 1 d . . .
C7 C 0.7130(2) 0.70761(15) 0.48565(9) 0.0142(3) Uani 1 1 d . . .
C8 C 0.7336(2) 0.72779(17) 0.39871(10) 0.0174(3) Uani 1 1 d . . .
H8 H 0.8088 0.7901 0.3697 0.021 Uiso 1 1 calc R . .
C9 C 0.6489(2) 0.66064(16) 0.35196(9) 0.0149(3) Uani 1 1 d . . .
C10 C 0.6716(2) 0.69662(17) 0.25764(9) 0.0160(3) Uani 1 1 d . . .
C11 C 0.7354(2) 0.58584(17) 0.21693(10) 0.0194(3) Uani 1 1 d . . .
C12 C 0.7534(2) 0.61416(18) 0.13025(10) 0.0226(3) Uani 1 1 d . . .
H12 H 0.8008 0.5355 0.1050 0.027 Uiso 1 1 calc R . .
C13 C 0.6994(2) 0.76188(19) 0.08200(10) 0.0215(3) Uani 1 1 d . . .
C14 C 0.6337(2) 0.87937(18) 0.11612(10) 0.0213(3) Uani 1 1 d . . .
H14 H 0.5973 0.9805 0.0813 0.026 Uiso 1 1 calc R . .
C15 C 0.6234(2) 0.84249(17) 0.20361(10) 0.0180(3) Uani 1 1 d . . .
C16 C 0.2448(2) 0.5866(2) 0.20655(11) 0.0259(4) Uani 1 1 d . . .
H16 H 0.2554 0.5484 0.2671 0.031 Uiso 1 1 calc R . .
C17 C 0.2843(3) 0.48726(19) 0.15755(11) 0.0254(3) Uani 1 1 d . . .
C18 C 0.2689(3) 0.54523(19) 0.06923(11) 0.0246(3) Uani 1 1 d . . .
H18 H 0.2962 0.4784 0.0355 0.030 Uiso 1 1 calc R . .
C19 C 0.2144(2) 0.69900(19) 0.02838(11) 0.0239(3) Uani 1 1 d . . .
C20 C 0.1767(2) 0.79451(19) 0.07933(11) 0.0251(3) Uani 1 1 d . . .
H20 H 0.1409 0.8994 0.0528 0.030 Uiso 1 1 calc R . .
C21 C 0.1904(2) 0.7400(2) 0.16812(11) 0.0254(4) Uani 1 1 d . . .
C22 C 0.3390(3) 0.3211(2) 0.20036(13) 0.0399(5) Uani 1 1 d . . .
H22A H 0.3660 0.2684 0.1568 0.060 Uiso 1 1 calc R . .
H22B H 0.2279 0.2991 0.2330 0.060 Uiso 1 1 calc R . .
H22C H 0.4586 0.2878 0.2390 0.060 Uiso 1 1 calc R . .
C23 C 0.1915(3) 0.7590(2) -0.06780(11) 0.0332(4) Uani 1 1 d . . .
H23A H 0.3051 0.7001 -0.0920 0.050 Uiso 1 1 calc R . .
H23B H 0.1878 0.8638 -0.0855 0.050 Uiso 1 1 calc R . .
H23C H 0.0670 0.7521 -0.0884 0.050 Uiso 1 1 calc R . .
C24 C 0.1416(3) 0.8458(2) 0.22182(13) 0.0329(4) Uani 1 1 d . . .
H24A H -0.0037 0.8839 0.2246 0.049 Uiso 1 1 calc R . .
H24B H 0.1924 0.9296 0.1961 0.049 Uiso 1 1 calc R . .
H24C H 0.2043 0.7927 0.2796 0.049 Uiso 1 1 calc R . .
F1 F 0.52250(12) 0.89807(10) 0.58604(6) 0.0208(2) Uani 1 1 d . . .
F2 F 1.11955(14) 0.95305(11) 0.66444(6) 0.0251(2) Uani 1 1 d . . .
F3 F 1.12597(13) 0.67376(10) 0.47723(6) 0.0218(2) Uani 1 1 d . . .
F4 F 0.78963(17) 0.44206(10) 0.26515(6) 0.0303(2) Uani 1 1 d . . .
F5 F 0.71144(16) 0.79385(12) -0.00376(6) 0.0312(2) Uani 1 1 d . . .
F6 F 0.55666(15) 0.95657(10) 0.23820(6) 0.0252(2) Uani 1 1 d . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O2 1.9172(10) . ?
Cu1 O2 1.9172(10) 2_666 ?
Cu1 O1 1.9262(10) 2_666 ?
Cu1 O1 1.9262(10) . ?
O1 C7 1.2747(18) . ?
O2 C9 1.2745(18) . ?
C1 F1 1.3481(16) . ?
C1 C2 1.381(2) . ?
C1 C6 1.391(2) . ?
C2 C3 1.381(2) . ?
C2 H2 0.9500 . ?
C3 F2 1.3503(16) . ?
C3 C4 1.378(2) . ?
C4 C5 1.373(2) . ?
C4 H4 0.9500 . ?
C5 F3 1.3565(16) . ?
C5 C6 1.395(2) . ?
C6 C7 1.4998(19) . ?
C7 C8 1.390(2) . ?
C8 C9 1.398(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.498(2) . ?
C10 C15 1.392(2) . ?
C10 C11 1.393(2) . ?
C11 F4 1.3439(18) . ?
C11 C12 1.376(2) . ?
C12 C13 1.375(2) . ?
C12 H12 0.9500 . ?
C13 F5 1.3544(18) . ?
C13 C14 1.377(2) . ?
C14 C15 1.379(2) . ?
C14 H14 0.9500 . ?
C15 F6 1.3535(17) . ?
C16 C21 1.388(3) . ?
C16 C17 1.398(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.387(2) . ?
C17 C22 1.508(3) . ?
C18 C19 1.398(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.394(2) . ?
C19 C23 1.508(2) . ?
C20 C21 1.392(2) . ?
C20 H20 0.9500 . ?
C21 C24 1.508(2) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 O2 180.00(6) . 2_666 ?
O2 Cu1 O1 86.57(4) . 2_666 ?
O2 Cu1 O1 93.43(4) 2_666 2_666 ?
O2 Cu1 O1 93.43(4) . . ?
O2 Cu1 O1 86.57(4) 2_666 . ?
O1 Cu1 O1 180.00(7) 2_666 . ?
C7 O1 Cu1 124.53(9) . . ?
C9 O2 Cu1 125.52(9) . . ?
F1 C1 C2 117.44(13) . . ?
F1 C1 C6 118.41(12) . . ?
C2 C1 C6 124.14(13) . . ?
C1 C2 C3 116.55(13) . . ?
C1 C2 H2 121.7 . . ?
C3 C2 H2 121.7 . . ?
F2 C3 C4 118.21(13) . . ?
F2 C3 C2 118.22(13) . . ?
C4 C3 C2 123.57(13) . . ?
C5 C4 C3 116.27(13) . . ?
C5 C4 H4 121.9 . . ?
C3 C4 H4 121.9 . . ?
F3 C5 C4 117.45(13) . . ?
F3 C5 C6 117.80(12) . . ?
C4 C5 C6 124.73(13) . . ?
C1 C6 C5 114.68(13) . . ?
C1 C6 C7 122.97(13) . . ?
C5 C6 C7 122.29(13) . . ?
O1 C7 C8 126.46(13) . . ?
O1 C7 C6 115.09(12) . . ?
C8 C7 C6 118.45(13) . . ?
C7 C8 C9 123.08(13) . . ?
C7 C8 H8 118.5 . . ?
C9 C8 H8 118.5 . . ?
O2 C9 C8 125.94(14) . . ?
O2 C9 C10 115.54(12) . . ?
C8 C9 C10 118.53(13) . . ?
C15 C10 C11 114.90(14) . . ?
C15 C10 C9 122.87(13) . . ?
C11 C10 C9 122.18(13) . . ?
F4 C11 C12 117.56(14) . . ?
F4 C11 C10 118.36(14) . . ?
C12 C11 C10 124.04(15) . . ?
C13 C12 C11 116.79(15) . . ?
C13 C12 H12 121.6 . . ?
C11 C12 H12 121.6 . . ?
F5 C13 C12 118.36(14) . . ?
F5 C13 C14 118.08(14) . . ?
C12 C13 C14 123.56(15) . . ?
C13 C14 C15 116.43(14) . . ?
C13 C14 H14 121.8 . . ?
C15 C14 H14 121.8 . . ?
F6 C15 C14 117.26(14) . . ?
F6 C15 C10 118.45(13) . . ?
C14 C15 C10 124.26(14) . . ?
C21 C16 C17 121.07(16) . . ?
C21 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C18 C17 C16 118.54(16) . . ?
C18 C17 C22 121.11(16) . . ?
C16 C17 C22 120.35(16) . . ?
C17 C18 C19 121.94(16) . . ?
C17 C18 H18 119.0 . . ?
C19 C18 H18 119.0 . . ?
C20 C19 C18 117.89(16) . . ?
C20 C19 C23 121.38(15) . . ?
C18 C19 C23 120.71(15) . . ?
C21 C20 C19 121.60(16) . . ?
C21 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?
C16 C21 C20 118.96(15) . . ?
C16 C21 C24 120.40(16) . . ?
C20 C21 C24 120.62(16) . . ?
C17 C22 H22A 109.5 . . ?
C17 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C17 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C19 C23 H23A 109.5 . . ?
C19 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C19 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 Cu1 O1 C7 -11.24(11) . . . . ?
O2 Cu1 O1 C7 168.76(11) 2_666 . . . ?
O1 Cu1 O1 C7 -102(72) 2_666 . . . ?
O2 Cu1 O2 C9 81(31) 2_666 . . . ?
O1 Cu1 O2 C9 -173.76(12) 2_666 . . . ?
O1 Cu1 O2 C9 6.24(12) . . . . ?
F1 C1 C2 C3 179.73(13) . . . . ?
C6 C1 C2 C3 -1.6(2) . . . . ?
C1 C2 C3 F2 -178.07(13) . . . . ?
C1 C2 C3 C4 1.9(2) . . . . ?
F2 C3 C4 C5 179.75(13) . . . . ?
C2 C3 C4 C5 -0.2(2) . . . . ?
C3 C4 C5 F3 179.62(13) . . . . ?
C3 C4 C5 C6 -2.0(2) . . . . ?
F1 C1 C6 C5 178.30(12) . . . . ?
C2 C1 C6 C5 -0.4(2) . . . . ?
F1 C1 C6 C7 -4.3(2) . . . . ?
C2 C1 C6 C7 176.99(14) . . . . ?
F3 C5 C6 C1 -179.35(12) . . . . ?
C4 C5 C6 C1 2.3(2) . . . . ?
F3 C5 C6 C7 3.3(2) . . . . ?
C4 C5 C6 C7 -175.11(14) . . . . ?
Cu1 O1 C7 C8 11.2(2) . . . . ?
Cu1 O1 C7 C6 -168.75(9) . . . . ?
C1 C6 C7 O1 -51.17(19) . . . . ?
C5 C6 C7 O1 125.99(15) . . . . ?
C1 C6 C7 C8 128.87(15) . . . . ?
C5 C6 C7 C8 -54.0(2) . . . . ?
O1 C7 C8 C9 -2.6(2) . . . . ?
C6 C7 C8 C9 177.32(13) . . . . ?
Cu1 O2 C9 C8 -0.6(2) . . . . ?
Cu1 O2 C9 C10 179.35(9) . . . . ?
C7 C8 C9 O2 -3.3(2) . . . . ?
C7 C8 C9 C10 176.82(14) . . . . ?
O2 C9 C10 C15 128.79(15) . . . . ?
C8 C9 C10 C15 -51.3(2) . . . . ?
O2 C9 C10 C11 -48.65(19) . . . . ?
C8 C9 C10 C11 131.27(16) . . . . ?
C15 C10 C11 F4 178.27(13) . . . . ?
C9 C10 C11 F4 -4.1(2) . . . . ?
C15 C10 C11 C12 0.6(2) . . . . ?
C9 C10 C11 C12 178.27(14) . . . . ?
F4 C11 C12 C13 -179.28(14) . . . . ?
C10 C11 C12 C13 -1.6(2) . . . . ?
C11 C12 C13 F5 -178.72(14) . . . . ?
C11 C12 C13 C14 1.3(2) . . . . ?
F5 C13 C14 C15 -179.98(13) . . . . ?
C12 C13 C14 C15 0.0(2) . . . . ?
C13 C14 C15 F6 -179.17(13) . . . . ?
C13 C14 C15 C10 -1.1(2) . . . . ?
C11 C10 C15 F6 178.84(13) . . . . ?
C9 C10 C15 F6 1.2(2) . . . . ?
C11 C10 C15 C14 0.8(2) . . . . ?
C9 C10 C15 C14 -176.80(14) . . . . ?
C21 C16 C17 C18 0.3(2) . . . . ?
C21 C16 C17 C22 -178.71(16) . . . . ?
C16 C17 C18 C19 -0.4(3) . . . . ?
C22 C17 C18 C19 178.66(17) . . . . ?
C17 C18 C19 C20 0.5(3) . . . . ?
C17 C18 C19 C23 -177.74(16) . . . . ?
C18 C19 C20 C21 -0.7(2) . . . . ?
C23 C19 C20 C21 177.58(16) . . . . ?
C17 C16 C21 C20 -0.5(2) . . . . ?
C17 C16 C21 C24 177.93(15) . . . . ?
C19 C20 C21 C16 0.7(2) . . . . ?
C19 C20 C21 C24 -177.74(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.973
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.973
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.052
_database_code_depnum_ccdc_archive 'CCDC 895495'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_100924a3
#TrackingRef 'web_deposit_cif_file_5_AkikoHori_1344479752.100924a3.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H14 Cu F8 O4'
_chemical_formula_sum            'C30 H14 Cu F8 O4'
_chemical_formula_weight         653.96

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.1345(5)
_cell_length_b                   7.3565(5)
_cell_length_c                   12.0946(8)
_cell_angle_alpha                97.5060(10)
_cell_angle_beta                 100.9420(10)
_cell_angle_gamma                94.5940(10)
_cell_volume                     614.31(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    100
_cell_measurement_reflns_used    5139
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      27.93

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.768
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             327
_exptl_absorpt_coefficient_mu    0.989
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8267
_exptl_absorpt_correction_T_max  0.9251
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            6953
_diffrn_reflns_av_R_equivalents  0.0130
_diffrn_reflns_av_sigmaI/netI    0.0153
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.81
_diffrn_reflns_theta_max         27.46
_reflns_number_total             2747
_reflns_number_gt                2613
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0259P)²+0.5520P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2747
_refine_ls_number_parameters     196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0244
_refine_ls_wR_factor_ref         0.0637
_refine_ls_wR_factor_gt          0.0630
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.5000 0.0000 1.0000 0.01269(8) Uani 1 2 d S . .
O1 O 0.49635(15) -0.09795(15) 0.84438(9) 0.0149(2) Uani 1 1 d . . .
O2 O 0.31720(16) 0.16749(15) 0.95877(9) 0.0166(2) Uani 1 1 d . . .
C1 C 0.6012(2) -0.1450(2) 0.61749(13) 0.0145(3) Uani 1 1 d . . .
C2 C 0.6335(2) -0.2227(2) 0.51351(13) 0.0175(3) Uani 1 1 d . . .
H2 H 0.7598 -0.2181 0.4988 0.021 Uiso 1 1 calc R . .
C3 C 0.4781(2) -0.3077(2) 0.43089(13) 0.0189(3) Uani 1 1 d . . .
H3 H 0.4980 -0.3623 0.3590 0.023 Uiso 1 1 calc R . .
C4 C 0.2940(2) -0.3137(2) 0.45256(13) 0.0188(3) Uani 1 1 d . . .
H4 H 0.1870 -0.3720 0.3964 0.023 Uiso 1 1 calc R . .
C5 C 0.2699(2) -0.2327(2) 0.55769(13) 0.0164(3) Uani 1 1 d . . .
C6 C 0.4196(2) -0.1456(2) 0.64417(12) 0.0134(3) Uani 1 1 d . . .
C7 C 0.3903(2) -0.0541(2) 0.75709(12) 0.0131(3) Uani 1 1 d . . .
C8 C 0.2547(2) 0.0735(2) 0.75820(13) 0.0152(3) Uani 1 1 d . . .
H8 H 0.1782 0.0910 0.6878 0.018 Uiso 1 1 calc R . .
C9 C 0.2274(2) 0.1756(2) 0.85821(13) 0.0130(3) Uani 1 1 d . . .
C10 C 0.0815(2) 0.3122(2) 0.85026(12) 0.0131(3) Uani 1 1 d . . .
C11 C 0.1098(2) 0.4753(2) 0.80652(13) 0.0160(3) Uani 1 1 d . . .
C12 C -0.0175(2) 0.6074(2) 0.80283(13) 0.0186(3) Uani 1 1 d . . .
H12 H 0.0091 0.7186 0.7739 0.022 Uiso 1 1 calc R . .
C13 C -0.1855(2) 0.5733(2) 0.84266(13) 0.0188(3) Uani 1 1 d . . .
H13 H -0.2760 0.6614 0.8400 0.023 Uiso 1 1 calc R . .
C14 C -0.2220(2) 0.4113(2) 0.88630(13) 0.0183(3) Uani 1 1 d . . .
H14 H -0.3374 0.3871 0.9127 0.022 Uiso 1 1 calc R . .
C15 C -0.0873(2) 0.2864(2) 0.89047(12) 0.0149(3) Uani 1 1 d . . .
F1 F 0.75304(13) -0.05764(13) 0.69613(8) 0.0199(2) Uani 1 1 d . . .
F2 F 0.08925(13) -0.24031(15) 0.57825(8) 0.0256(2) Uani 1 1 d . . .
F3 F 0.27395(14) 0.50656(14) 0.76728(9) 0.0246(2) Uani 1 1 d . . .
F4 F -0.11927(14) 0.13102(13) 0.93568(8) 0.0210(2) Uani 1 1 d . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O2 1.9075(10) 2_657 ?
Cu1 O2 1.9076(10) . ?
Cu1 O1 1.9200(10) . ?
Cu1 O1 1.9200(10) 2_657 ?
O1 C7 1.2714(18) . ?
O2 C9 1.2737(18) . ?
C1 F1 1.3524(17) . ?
C1 C2 1.380(2) . ?
C1 C6 1.393(2) . ?
C2 C3 1.387(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.386(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.379(2) . ?
C4 H4 0.9500 . ?
C5 F2 1.3563(17) . ?
C5 C6 1.392(2) . ?
C6 C7 1.5009(19) . ?
C7 C8 1.401(2) . ?
C8 C9 1.393(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.5026(19) . ?
C10 C11 1.388(2) . ?
C10 C15 1.390(2) . ?
C11 F3 1.3589(18) . ?
C11 C12 1.381(2) . ?
C12 C13 1.391(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.390(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.381(2) . ?
C14 H14 0.9500 . ?
C15 F4 1.3512(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 O2 179.999(1) 2_657 . ?
O2 Cu1 O1 86.86(4) 2_657 . ?
O2 Cu1 O1 93.14(4) . . ?
O2 Cu1 O1 93.14(4) 2_657 2_657 ?
O2 Cu1 O1 86.86(4) . 2_657 ?
O1 Cu1 O1 179.999(1) . 2_657 ?
C7 O1 Cu1 126.03(10) . . ?
C9 O2 Cu1 125.84(10) . . ?
F1 C1 C2 118.23(14) . . ?
F1 C1 C6 118.24(13) . . ?
C2 C1 C6 123.49(14) . . ?
C1 C2 C3 118.79(14) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 120.42(14) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C5 C4 C3 118.35(15) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
F2 C5 C4 117.87(14) . . ?
F2 C5 C6 118.11(13) . . ?
C4 C5 C6 124.02(14) . . ?
C5 C6 C1 114.92(13) . . ?
C5 C6 C7 123.32(13) . . ?
C1 C6 C7 121.73(13) . . ?
O1 C7 C8 125.69(14) . . ?
O1 C7 C6 115.80(13) . . ?
C8 C7 C6 118.49(13) . . ?
C9 C8 C7 122.73(14) . . ?
C9 C8 H8 118.6 . . ?
C7 C8 H8 118.6 . . ?
O2 C9 C8 126.29(14) . . ?
O2 C9 C10 114.99(13) . . ?
C8 C9 C10 118.72(13) . . ?
C11 C10 C15 115.75(14) . . ?
C11 C10 C9 122.28(13) . . ?
C15 C10 C9 121.92(13) . . ?
F3 C11 C12 118.76(14) . . ?
F3 C11 C10 117.57(13) . . ?
C12 C11 C10 123.66(15) . . ?
C11 C12 C13 118.20(15) . . ?
C11 C12 H12 120.9 . . ?
C13 C12 H12 120.9 . . ?
C14 C13 C12 120.54(14) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C15 C14 C13 118.68(15) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
F4 C15 C14 119.03(14) . . ?
F4 C15 C10 117.81(13) . . ?
C14 C15 C10 123.15(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 Cu1 O1 C7 176.86(13) 2_657 . . . ?
O2 Cu1 O1 C7 -3.14(13) . . . . ?
O1 Cu1 O1 C7 -68(22) 2_657 . . . ?
O2 Cu1 O2 C9 26(5) 2_657 . . . ?
O1 Cu1 O2 C9 5.72(13) . . . . ?
O1 Cu1 O2 C9 -174.28(13) 2_657 . . . ?
F1 C1 C2 C3 -178.04(13) . . . . ?
C6 C1 C2 C3 -0.6(2) . . . . ?
C1 C2 C3 C4 0.2(2) . . . . ?
C2 C3 C4 C5 0.2(2) . . . . ?
C3 C4 C5 F2 -179.60(14) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
F2 C5 C6 C1 179.29(13) . . . . ?
C4 C5 C6 C1 -0.1(2) . . . . ?
F2 C5 C6 C7 -2.2(2) . . . . ?
C4 C5 C6 C7 178.42(14) . . . . ?
F1 C1 C6 C5 177.95(13) . . . . ?
C2 C1 C6 C5 0.5(2) . . . . ?
F1 C1 C6 C7 -0.6(2) . . . . ?
C2 C1 C6 C7 -178.02(14) . . . . ?
Cu1 O1 C7 C8 -0.5(2) . . . . ?
Cu1 O1 C7 C6 177.87(9) . . . . ?
C5 C6 C7 O1 130.41(16) . . . . ?
C1 C6 C7 O1 -51.2(2) . . . . ?
C5 C6 C7 C8 -51.1(2) . . . . ?
C1 C6 C7 C8 127.27(16) . . . . ?
O1 C7 C8 C9 3.3(3) . . . . ?
C6 C7 C8 C9 -175.07(14) . . . . ?
Cu1 O2 C9 C8 -4.9(2) . . . . ?
Cu1 O2 C9 C10 176.13(10) . . . . ?
C7 C8 C9 O2 -0.3(3) . . . . ?
C7 C8 C9 C10 178.59(14) . . . . ?
O2 C9 C10 C11 108.24(16) . . . . ?
C8 C9 C10 C11 -70.8(2) . . . . ?
O2 C9 C10 C15 -69.21(19) . . . . ?
C8 C9 C10 C15 111.75(17) . . . . ?
C15 C10 C11 F3 179.42(13) . . . . ?
C9 C10 C11 F3 1.8(2) . . . . ?
C15 C10 C11 C12 0.6(2) . . . . ?
C9 C10 C11 C12 -176.95(14) . . . . ?
F3 C11 C12 C13 179.64(13) . . . . ?
C10 C11 C12 C13 -1.6(2) . . . . ?
C11 C12 C13 C14 0.9(2) . . . . ?
C12 C13 C14 C15 0.7(2) . . . . ?
C13 C14 C15 F4 178.18(13) . . . . ?
C13 C14 C15 C10 -1.8(2) . . . . ?
C11 C10 C15 F4 -178.86(13) . . . . ?
C9 C10 C15 F4 -1.2(2) . . . . ?
C11 C10 C15 C14 1.1(2) . . . . ?
C9 C10 C15 C14 178.69(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.972
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.055


_database_code_depnum_ccdc_archive 'CCDC 895496'
