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# CCDC
#
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# 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.
#
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# fide research purposes only. It may contain copyright material
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data_lwz01
#TrackingRef 'complex1.CIF'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C40 H36 F9 Nd O14'
_chemical_formula_sum 'C40 H36 F9 Nd O14'
_chemical_formula_weight 1055.93
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'
Nd Nd -0.1943 3.0179 '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'
_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 13.228(3)
_cell_length_b 12.583(3)
_cell_length_c 26.182(8)
_cell_angle_alpha 90.00
_cell_angle_beta 108.30(3)
_cell_angle_gamma 90.00
_cell_volume 4137.5(19)
_cell_formula_units_Z 4
_cell_measurement_temperature 293(2)
_cell_measurement_reflns_used 28719
_cell_measurement_theta_min 3.10
_cell_measurement_theta_max 27.48
_exptl_crystal_description block
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.41
_exptl_crystal_size_mid 0.26
_exptl_crystal_size_min 0.17
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.695
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 2116
_exptl_absorpt_coefficient_mu 1.363
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.6082
_exptl_absorpt_correction_T_max 0.7974
_exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 293(2)
_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 'Rigaku RAXIS-RAPID'
_diffrn_measurement_method '\w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time 0
_diffrn_standards_decay_% 0
_diffrn_reflns_number 37536
_diffrn_reflns_av_R_equivalents 0.0647
_diffrn_reflns_av_sigmaI/netI 0.0547
_diffrn_reflns_limit_h_min -17
_diffrn_reflns_limit_h_max 17
_diffrn_reflns_limit_k_min -16
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_l_min -33
_diffrn_reflns_limit_l_max 33
_diffrn_reflns_theta_min 3.10
_diffrn_reflns_theta_max 27.48
_reflns_number_total 9304
_reflns_number_gt 6740
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'RAPID-AUTO (Rigaku 1998 RAPID-AUTO)'
_computing_cell_refinement 'RAPID-AUTO (Rigaku 1998 RAPID-AUTO)'
_computing_data_reduction 'CrystalClear (Rigaku/MSC, 2002)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)'
_computing_publication_material SHELXL-97
_refine_special_details
;
dfix 0.85 0.01 h131 o13
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0524P)^2^+6.3506P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 9304
_refine_ls_number_parameters 587
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0760
_refine_ls_R_factor_gt 0.0508
_refine_ls_wR_factor_ref 0.1248
_refine_ls_wR_factor_gt 0.1124
_refine_ls_goodness_of_fit_ref 1.065
_refine_ls_restrained_S_all 1.065
_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
C1 C 0.7502(4) 0.5938(3) 0.20478(19) 0.0373(11) Uani 1 1 d . . .
C2 C 0.8256(4) 0.6378(4) 0.1820(2) 0.0396(11) Uani 1 1 d . . .
C3 C 0.8813(5) 0.7314(4) 0.2162(2) 0.0476(13) Uani 1 1 d . . .
H3A H 0.9575 0.7198 0.2304 0.057 Uiso 1 1 calc R . .
H3B H 0.8680 0.7970 0.1956 0.057 Uiso 1 1 calc R . .
C4 C 0.8309(4) 0.7339(4) 0.2607(2) 0.0420(12) Uani 1 1 d . . .
C5 C 0.8524(5) 0.8000(4) 0.3053(2) 0.0499(14) Uani 1 1 d . . .
H5 H 0.9042 0.8525 0.3112 0.060 Uiso 1 1 calc R . .
C6 C 0.7951(5) 0.7860(4) 0.3409(2) 0.0461(13) Uani 1 1 d . . .
C7 C 0.7148(4) 0.7075(4) 0.3319(2) 0.0417(11) Uani 1 1 d . . .
C8 C 0.6959(5) 0.6415(4) 0.2878(2) 0.0423(12) Uani 1 1 d . . .
H8 H 0.6445 0.5885 0.2817 0.051 Uiso 1 1 calc R . .
C9 C 0.7545(4) 0.6550(4) 0.25285(19) 0.0378(11) Uani 1 1 d . . .
C10 C 0.8384(4) 0.5979(4) 0.13550(19) 0.0372(10) Uani 1 1 d . . .
C11 C 0.9198(5) 0.6503(5) 0.1131(2) 0.0475(13) Uani 1 1 d . . .
C12 C 0.8915(6) 0.9208(5) 0.4008(3) 0.073(2) Uani 1 1 d . . .
H12A H 0.9578 0.8899 0.4007 0.109 Uiso 1 1 calc R . .
H12B H 0.8988 0.9486 0.4359 0.109 Uiso 1 1 calc R . .
H12C H 0.8726 0.9772 0.3748 0.109 Uiso 1 1 calc R . .
C13 C 0.5953(5) 0.6141(5) 0.3662(2) 0.0607(16) Uani 1 1 d . . .
H13A H 0.5389 0.6150 0.3324 0.091 Uiso 1 1 calc R . .
H13B H 0.5655 0.6171 0.3952 0.091 Uiso 1 1 calc R . .
H13C H 0.6359 0.5499 0.3689 0.091 Uiso 1 1 calc R . .
C14 C 0.8462(4) 0.2020(4) 0.1460(2) 0.0415(12) Uani 1 1 d . . .
C15 C 0.8173(5) 0.1531(4) 0.1892(2) 0.0446(12) Uani 1 1 d . . .
C16 C 0.8826(5) 0.0525(4) 0.2054(2) 0.0511(14) Uani 1 1 d . . .
H16A H 0.9264 0.0554 0.2429 0.061 Uiso 1 1 calc R . .
H16B H 0.8370 -0.0096 0.2000 0.061 Uiso 1 1 calc R . .
C17 C 0.9504(5) 0.0500(4) 0.1690(2) 0.0480(13) Uani 1 1 d . . .
C18 C 1.0310(5) -0.0181(4) 0.1675(2) 0.0507(14) Uani 1 1 d . . .
H18 H 1.0518 -0.0730 0.1924 0.061 Uiso 1 1 calc R . .
C19 C 1.0810(5) -0.0040(4) 0.1286(2) 0.0530(15) Uani 1 1 d . . .
C20 C 1.0462(4) 0.0767(4) 0.0890(2) 0.0464(12) Uani 1 1 d . . .
C21 C 0.9691(4) 0.1478(4) 0.0916(2) 0.0456(13) Uani 1 1 d . . .
H21 H 0.9481 0.2028 0.0668 0.055 Uiso 1 1 calc R . .
C22 C 0.9231(5) 0.1353(4) 0.1323(2) 0.0461(13) Uani 1 1 d . . .
C23 C 1.2107(6) -0.1378(5) 0.1665(3) 0.073(2) Uani 1 1 d . . .
H23A H 1.2287 -0.1026 0.2008 0.110 Uiso 1 1 calc R . .
H23B H 1.2740 -0.1670 0.1615 0.110 Uiso 1 1 calc R . .
H23C H 1.1610 -0.1939 0.1655 0.110 Uiso 1 1 calc R . .
C24 C 1.0539(6) 0.1444(6) 0.0055(3) 0.0654(17) Uani 1 1 d . . .
H24A H 0.9789 0.1315 -0.0095 0.098 Uiso 1 1 calc R . .
H24B H 1.0881 0.1298 -0.0211 0.098 Uiso 1 1 calc R . .
H24C H 1.0657 0.2173 0.0166 0.098 Uiso 1 1 calc R . .
C25 C 0.7401(5) 0.1935(4) 0.20762(18) 0.0427(12) Uani 1 1 d . . .
C26 C 0.7028(5) 0.1280(4) 0.2478(2) 0.0458(13) Uani 1 1 d . . .
C27 C 0.6226(4) 0.1557(3) 0.05148(17) 0.0328(10) Uani 1 1 d . . .
C28 C 0.6646(4) 0.1903(4) 0.00989(18) 0.0355(10) Uani 1 1 d . . .
C29 C 0.6963(5) 0.0940(4) -0.0167(2) 0.0420(12) Uani 1 1 d . . .
H29A H 0.6563 0.0907 -0.0547 0.050 Uiso 1 1 calc R . .
H29B H 0.7719 0.0946 -0.0124 0.050 Uiso 1 1 calc R . .
C30 C 0.6677(4) 0.0026(3) 0.01396(18) 0.0335(10) Uani 1 1 d . . .
C31 C 0.6791(4) -0.1061(3) 0.00696(19) 0.0366(10) Uani 1 1 d . . .
H31 H 0.7062 -0.1310 -0.0196 0.044 Uiso 1 1 calc R . .
C32 C 0.6495(4) -0.1751(4) 0.03999(19) 0.0377(11) Uani 1 1 d . . .
C33 C 0.6102(4) -0.1389(4) 0.08134(19) 0.0376(11) Uani 1 1 d . . .
C34 C 0.5995(4) -0.0320(3) 0.08814(19) 0.0361(11) Uani 1 1 d . . .
H34 H 0.5745 -0.0069 0.1154 0.043 Uiso 1 1 calc R . .
C35 C 0.6270(4) 0.0390(4) 0.05335(18) 0.0334(10) Uani 1 1 d . . .
C36 C 0.5555(6) -0.1874(5) 0.1564(2) 0.0629(18) Uani 1 1 d . . .
H36A H 0.6109 -0.1455 0.1805 0.094 Uiso 1 1 calc R . .
H36B H 0.5437 -0.2500 0.1748 0.094 Uiso 1 1 calc R . .
H36C H 0.4911 -0.1464 0.1447 0.094 Uiso 1 1 calc R . .
C37 C 0.6801(6) -0.3282(4) -0.0078(2) 0.0564(16) Uani 1 1 d . . .
H37A H 0.6278 -0.3062 -0.0406 0.085 Uiso 1 1 calc R . .
H37B H 0.6802 -0.4044 -0.0053 0.085 Uiso 1 1 calc R . .
H37C H 0.7492 -0.3041 -0.0075 0.085 Uiso 1 1 calc R . .
C38 C 0.6720(4) 0.2958(3) -0.00140(18) 0.0368(11) Uani 1 1 d . . .
C39 C 0.7247(6) 0.3275(4) -0.0434(2) 0.0523(15) Uani 1 1 d . . .
C40 C 0.4511(8) 0.4451(8) 0.1732(4) 0.108(3) Uani 1 1 d . . .
H40A H 0.4737 0.4102 0.2076 0.162 Uiso 1 1 calc R . .
H40B H 0.3750 0.4520 0.1613 0.162 Uiso 1 1 calc R . .
H40C H 0.4830 0.5143 0.1765 0.162 Uiso 1 1 calc R . .
F1 F 0.9237(3) 0.6073(3) 0.06804(15) 0.0716(10) Uani 1 1 d . . .
F2 F 1.0173(3) 0.6459(4) 0.14779(17) 0.0868(13) Uani 1 1 d . . .
F3 F 0.8992(4) 0.7540(3) 0.10304(16) 0.0744(11) Uani 1 1 d . . .
F4 F 0.6327(4) 0.1776(3) 0.26595(16) 0.0877(13) Uani 1 1 d . . .
F5 F 0.6560(4) 0.0390(3) 0.22656(15) 0.0834(13) Uani 1 1 d . . .
F6 F 0.7807(3) 0.1013(4) 0.29127(15) 0.0967(16) Uani 1 1 d . . .
F7 F 0.7166(6) 0.4262(3) -0.0554(2) 0.128(2) Uani 1 1 d . . .
F8 F 0.6762(6) 0.2840(5) -0.09100(19) 0.146(3) Uani 1 1 d . . .
F9 F 0.8174(5) 0.2950(6) -0.0347(3) 0.175(4) Uani 1 1 d . . .
Nd1 Nd 0.65741(2) 0.392154(18) 0.114801(9) 0.03324(9) Uani 1 1 d . . .
O1 O 0.6888(3) 0.5157(3) 0.18826(13) 0.0447(9) Uani 1 1 d . . .
O2 O 0.7886(3) 0.5203(3) 0.10798(13) 0.0426(8) Uani 1 1 d . . .
O3 O 0.6624(3) 0.7027(3) 0.36906(14) 0.0522(10) Uani 1 1 d . . .
O4 O 0.8108(4) 0.8419(3) 0.38736(15) 0.0657(12) Uani 1 1 d . . .
O5 O 0.8129(3) 0.2895(3) 0.12252(14) 0.0454(9) Uani 1 1 d . . .
O6 O 0.6887(3) 0.2798(3) 0.19352(13) 0.0485(9) Uani 1 1 d . . .
O7 O 1.1639(4) -0.0631(4) 0.12467(17) 0.0642(12) Uani 1 1 d . . .
O8 O 1.0971(3) 0.0770(3) 0.05077(17) 0.0599(11) Uani 1 1 d . . .
O9 O 0.5881(3) 0.2124(2) 0.08234(13) 0.0379(8) Uani 1 1 d . . .
O10 O 0.6422(3) 0.3755(2) 0.02064(13) 0.0419(8) Uani 1 1 d . . .
O11 O 0.5861(4) -0.2174(3) 0.11134(15) 0.0541(10) Uani 1 1 d . . .
O12 O 0.6551(3) -0.2837(2) 0.03688(14) 0.0481(9) Uani 1 1 d . . .
O13 O 0.4827(4) 0.3846(3) 0.13560(16) 0.0543(10) Uani 1 1 d D . .
H131 H 0.445(5) 0.331(4) 0.137(3) 0.081 Uiso 1 1 d D . .
O14 O 0.5435(3) 0.5479(3) 0.06872(15) 0.0500(9) Uani 1 1 d . . .
H142 H 0.5774 0.5972 0.0648 0.075 Uiso 1 1 d R . .
H141 H 0.4831 0.5474 0.0380 0.075 Uiso 1 1 d R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.043(3) 0.026(2) 0.043(3) -0.0009(18) 0.013(2) -0.003(2)
C2 0.050(3) 0.026(2) 0.045(3) -0.0011(18) 0.018(2) -0.005(2)
C3 0.056(4) 0.035(3) 0.055(3) -0.010(2) 0.021(3) -0.013(2)
C4 0.045(3) 0.034(3) 0.045(3) -0.001(2) 0.012(2) -0.006(2)
C5 0.059(4) 0.033(3) 0.053(3) -0.012(2) 0.012(3) -0.017(2)
C6 0.063(4) 0.031(3) 0.042(3) -0.008(2) 0.012(2) -0.004(2)
C7 0.045(3) 0.037(3) 0.046(3) -0.005(2) 0.019(2) -0.001(2)
C8 0.050(3) 0.034(3) 0.044(3) -0.001(2) 0.016(2) -0.002(2)
C9 0.039(3) 0.033(2) 0.043(3) -0.0042(19) 0.013(2) 0.001(2)
C10 0.034(3) 0.033(2) 0.046(3) 0.008(2) 0.014(2) 0.003(2)
C11 0.046(3) 0.053(3) 0.046(3) 0.003(2) 0.016(2) 0.001(3)
C12 0.097(6) 0.054(4) 0.061(4) -0.025(3) 0.015(4) -0.024(4)
C13 0.068(4) 0.070(4) 0.053(3) -0.015(3) 0.032(3) -0.017(3)
C14 0.040(3) 0.027(2) 0.052(3) 0.001(2) 0.007(2) 0.000(2)
C15 0.048(3) 0.039(3) 0.042(3) 0.005(2) 0.008(2) -0.001(2)
C16 0.061(4) 0.036(3) 0.059(3) 0.016(2) 0.022(3) 0.007(3)
C17 0.052(4) 0.030(3) 0.057(3) 0.006(2) 0.010(3) 0.006(2)
C18 0.052(4) 0.036(3) 0.060(3) 0.010(2) 0.012(3) 0.005(2)
C19 0.052(4) 0.033(3) 0.066(4) 0.000(2) 0.007(3) 0.008(2)
C20 0.039(3) 0.038(3) 0.062(3) 0.002(2) 0.016(2) 0.001(2)
C21 0.044(3) 0.032(3) 0.055(3) 0.008(2) 0.008(2) 0.000(2)
C22 0.050(3) 0.034(3) 0.052(3) 0.006(2) 0.011(2) -0.002(2)
C23 0.069(5) 0.057(4) 0.091(5) 0.016(3) 0.019(4) 0.027(3)
C24 0.065(4) 0.071(4) 0.066(4) 0.013(3) 0.029(3) 0.007(3)
C25 0.055(3) 0.035(3) 0.034(2) -0.0027(19) 0.007(2) -0.005(2)
C26 0.053(3) 0.041(3) 0.041(3) 0.005(2) 0.012(2) -0.003(2)
C27 0.040(3) 0.019(2) 0.039(2) -0.0025(17) 0.012(2) -0.0018(18)
C28 0.040(3) 0.031(2) 0.036(2) -0.0059(18) 0.013(2) -0.001(2)
C29 0.059(3) 0.027(2) 0.047(3) -0.0048(19) 0.028(2) -0.002(2)
C30 0.038(3) 0.021(2) 0.040(2) -0.0012(17) 0.010(2) 0.0014(18)
C31 0.042(3) 0.025(2) 0.041(2) -0.0025(19) 0.012(2) 0.003(2)
C32 0.041(3) 0.024(2) 0.046(3) -0.0002(19) 0.010(2) 0.0021(19)
C33 0.046(3) 0.023(2) 0.044(3) 0.0051(18) 0.016(2) 0.0033(19)
C34 0.044(3) 0.022(2) 0.044(3) -0.0019(18) 0.017(2) 0.0023(19)
C35 0.033(3) 0.027(2) 0.038(2) -0.0026(17) 0.0091(19) -0.0014(18)
C36 0.099(6) 0.040(3) 0.059(3) 0.011(3) 0.038(3) 0.003(3)
C37 0.089(5) 0.024(3) 0.055(3) -0.006(2) 0.022(3) 0.003(3)
C38 0.051(3) 0.024(2) 0.036(2) -0.0012(17) 0.015(2) 0.001(2)
C39 0.080(5) 0.032(3) 0.057(3) 0.000(2) 0.039(3) 0.004(3)
C40 0.102(7) 0.135(8) 0.112(7) -0.055(6) 0.070(6) -0.043(6)
F1 0.082(3) 0.079(3) 0.070(2) -0.0086(19) 0.048(2) -0.016(2)
F2 0.043(2) 0.135(4) 0.082(3) 0.012(2) 0.0176(19) -0.010(2)
F3 0.097(3) 0.045(2) 0.096(3) 0.0138(18) 0.052(2) -0.0107(19)
F4 0.127(4) 0.074(3) 0.086(3) 0.018(2) 0.068(3) 0.012(3)
F5 0.118(4) 0.067(2) 0.075(2) -0.0151(19) 0.044(2) -0.044(2)
F6 0.072(3) 0.144(4) 0.059(2) 0.053(2) 0.0003(19) -0.009(3)
F7 0.239(7) 0.040(2) 0.170(5) 0.026(3) 0.159(5) 0.011(3)
F8 0.247(8) 0.145(5) 0.078(3) -0.028(3) 0.094(4) -0.081(5)
F9 0.110(5) 0.248(8) 0.213(7) 0.161(6) 0.116(5) 0.082(5)
Nd1 0.04541(16) 0.02006(12) 0.03488(14) -0.00143(10) 0.01351(10) -0.00066(11)
O1 0.056(2) 0.0378(19) 0.0457(19) -0.0107(15) 0.0229(17) -0.0176(17)
O2 0.057(2) 0.0313(18) 0.0450(19) -0.0040(14) 0.0232(17) -0.0036(16)
O3 0.068(3) 0.046(2) 0.051(2) -0.0139(16) 0.0296(19) -0.0080(19)
O4 0.089(4) 0.059(3) 0.051(2) -0.0229(19) 0.024(2) -0.023(2)
O5 0.054(2) 0.0318(18) 0.050(2) 0.0072(15) 0.0163(17) 0.0028(16)
O6 0.068(3) 0.0363(19) 0.0433(19) 0.0046(15) 0.0200(18) 0.0052(18)
O7 0.061(3) 0.053(2) 0.078(3) 0.009(2) 0.020(2) 0.022(2)
O8 0.052(3) 0.062(3) 0.071(3) 0.011(2) 0.025(2) 0.011(2)
O9 0.051(2) 0.0224(15) 0.0446(18) -0.0052(13) 0.0217(15) -0.0037(14)
O10 0.064(3) 0.0232(17) 0.0409(18) 0.0011(12) 0.0206(16) 0.0035(15)
O11 0.084(3) 0.0257(18) 0.063(2) 0.0081(16) 0.038(2) 0.0035(18)
O12 0.073(3) 0.0189(16) 0.054(2) -0.0024(14) 0.0228(18) 0.0041(16)
O13 0.064(3) 0.042(2) 0.062(2) -0.0039(18) 0.028(2) -0.0074(19)
O14 0.053(2) 0.0292(19) 0.067(2) 0.0079(16) 0.0170(19) 0.0016(16)
_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
C1 O1 1.261(5) . ?
C1 C2 1.425(7) . ?
C1 C9 1.461(7) . ?
C2 C10 1.375(7) . ?
C2 C3 1.523(7) . ?
C3 C4 1.514(8) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C9 1.385(7) . ?
C4 C5 1.389(7) . ?
C5 C6 1.383(8) . ?
C5 H5 0.9300 . ?
C6 O4 1.365(6) . ?
C6 C7 1.415(7) . ?
C7 O3 1.362(6) . ?
C7 C8 1.380(7) . ?
C8 C9 1.382(7) . ?
C8 H8 0.9300 . ?
C10 O2 1.268(6) . ?
C10 C11 1.529(7) . ?
C11 F1 1.314(6) . ?
C11 F2 1.324(7) . ?
C11 F3 1.341(7) . ?
C12 O4 1.418(8) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 O3 1.413(7) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 O5 1.270(6) . ?
C14 C15 1.442(7) . ?
C14 C22 1.448(8) . ?
C15 C25 1.357(8) . ?
C15 C16 1.516(7) . ?
C16 C17 1.501(8) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.377(8) . ?
C17 C22 1.409(7) . ?
C18 C19 1.389(9) . ?
C18 H18 0.9300 . ?
C19 O7 1.356(7) . ?
C19 C20 1.421(7) . ?
C20 O8 1.371(7) . ?
C20 C21 1.374(8) . ?
C21 C22 1.392(8) . ?
C21 H21 0.9300 . ?
C23 O7 1.429(7) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 O8 1.422(7) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 O6 1.273(6) . ?
C25 C26 1.536(7) . ?
C26 F5 1.315(6) . ?
C26 F6 1.316(6) . ?
C26 F4 1.323(7) . ?
C27 O9 1.265(5) . ?
C27 C28 1.437(7) . ?
C27 C35 1.469(6) . ?
C28 C38 1.370(6) . ?
C28 C29 1.521(6) . ?
C29 C30 1.518(6) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C35 1.383(6) . ?
C30 C31 1.394(6) . ?
C31 C32 1.367(7) . ?
C31 H31 0.9300 . ?
C32 O12 1.372(5) . ?
C32 C33 1.416(7) . ?
C33 O11 1.360(6) . ?
C33 C34 1.370(6) . ?
C34 C35 1.403(6) . ?
C34 H34 0.9300 . ?
C36 O11 1.414(7) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 O12 1.426(6) . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 O10 1.279(5) . ?
C38 C39 1.530(7) . ?
C39 F9 1.245(8) . ?
C39 F7 1.277(7) . ?
C39 F8 1.327(7) . ?
C40 O13 1.409(8) . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
Nd1 O5 2.383(4) . ?
Nd1 O1 2.405(3) . ?
Nd1 O2 2.416(4) . ?
Nd1 O10 2.419(3) . ?
Nd1 O6 2.425(3) . ?
Nd1 O9 2.488(3) . ?
Nd1 O14 2.535(3) . ?
Nd1 O13 2.537(4) . ?
O13 H131 0.848(10) . ?
O14 H142 0.7906 . ?
O14 H141 0.9399 . ?
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 C1 C2 128.2(5) . . ?
O1 C1 C9 123.6(5) . . ?
C2 C1 C9 108.2(4) . . ?
C10 C2 C1 121.7(4) . . ?
C10 C2 C3 129.1(5) . . ?
C1 C2 C3 109.1(4) . . ?
C4 C3 C2 102.7(4) . . ?
C4 C3 H3A 111.2 . . ?
C2 C3 H3A 111.2 . . ?
C4 C3 H3B 111.2 . . ?
C2 C3 H3B 111.2 . . ?
H3A C3 H3B 109.1 . . ?
C9 C4 C5 120.1(5) . . ?
C9 C4 C3 110.4(4) . . ?
C5 C4 C3 129.5(5) . . ?
C6 C5 C4 118.6(5) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
O4 C6 C5 124.9(5) . . ?
O4 C6 C7 113.8(5) . . ?
C5 C6 C7 121.2(4) . . ?
O3 C7 C8 124.9(5) . . ?
O3 C7 C6 115.9(4) . . ?
C8 C7 C6 119.2(5) . . ?
C7 C8 C9 119.2(5) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C8 C9 C4 121.6(5) . . ?
C8 C9 C1 128.8(5) . . ?
C4 C9 C1 109.6(4) . . ?
O2 C10 C2 126.7(5) . . ?
O2 C10 C11 114.7(4) . . ?
C2 C10 C11 118.7(4) . . ?
F1 C11 F2 107.1(5) . . ?
F1 C11 F3 106.7(4) . . ?
F2 C11 F3 105.6(5) . . ?
F1 C11 C10 113.4(5) . . ?
F2 C11 C10 111.7(4) . . ?
F3 C11 C10 111.7(5) . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O5 C14 C15 127.8(5) . . ?
O5 C14 C22 123.1(5) . . ?
C15 C14 C22 109.0(4) . . ?
C25 C15 C14 122.2(5) . . ?
C25 C15 C16 129.8(5) . . ?
C14 C15 C16 108.0(5) . . ?
C17 C16 C15 104.0(4) . . ?
C17 C16 H16A 111.0 . . ?
C15 C16 H16A 111.0 . . ?
C17 C16 H16B 111.0 . . ?
C15 C16 H16B 111.0 . . ?
H16A C16 H16B 109.0 . . ?
C18 C17 C22 119.3(6) . . ?
C18 C17 C16 130.7(5) . . ?
C22 C17 C16 109.9(5) . . ?
C17 C18 C19 119.4(5) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?
O7 C19 C18 124.7(5) . . ?
O7 C19 C20 114.9(6) . . ?
C18 C19 C20 120.5(5) . . ?
O8 C20 C21 125.2(5) . . ?
O8 C20 C19 114.5(5) . . ?
C21 C20 C19 120.3(6) . . ?
C20 C21 C22 118.3(5) . . ?
C20 C21 H21 120.9 . . ?
C22 C21 H21 120.9 . . ?
C21 C22 C17 121.8(5) . . ?
C21 C22 C14 129.3(5) . . ?
C17 C22 C14 108.8(5) . . ?
O7 C23 H23A 109.5 . . ?
O7 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O7 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O8 C24 H24A 109.5 . . ?
O8 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O8 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O6 C25 C15 127.6(5) . . ?
O6 C25 C26 113.5(5) . . ?
C15 C25 C26 118.8(5) . . ?
F5 C26 F6 106.6(5) . . ?
F5 C26 F4 105.4(5) . . ?
F6 C26 F4 104.9(5) . . ?
F5 C26 C25 112.1(4) . . ?
F6 C26 C25 113.3(5) . . ?
F4 C26 C25 113.9(4) . . ?
O9 C27 C28 128.0(4) . . ?
O9 C27 C35 124.1(4) . . ?
C28 C27 C35 107.9(4) . . ?
C38 C28 C27 121.9(4) . . ?
C38 C28 C29 128.6(4) . . ?
C27 C28 C29 109.5(4) . . ?
C30 C29 C28 102.2(4) . . ?
C30 C29 H29A 111.3 . . ?
C28 C29 H29A 111.3 . . ?
C30 C29 H29B 111.3 . . ?
C28 C29 H29B 111.3 . . ?
H29A C29 H29B 109.2 . . ?
C35 C30 C31 120.4(4) . . ?
C35 C30 C29 111.3(4) . . ?
C31 C30 C29 128.2(4) . . ?
C32 C31 C30 118.4(5) . . ?
C32 C31 H31 120.8 . . ?
C30 C31 H31 120.8 . . ?
C31 C32 O12 124.3(5) . . ?
C31 C32 C33 121.8(4) . . ?
O12 C32 C33 113.9(4) . . ?
O11 C33 C34 125.8(5) . . ?
O11 C33 C32 114.6(4) . . ?
C34 C33 C32 119.5(4) . . ?
C33 C34 C35 118.9(4) . . ?
C33 C34 H34 120.6 . . ?
C35 C34 H34 120.6 . . ?
C30 C35 C34 120.9(4) . . ?
C30 C35 C27 109.1(4) . . ?
C34 C35 C27 130.0(4) . . ?
O11 C36 H36A 109.5 . . ?
O11 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
O11 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
O12 C37 H37A 109.5 . . ?
O12 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
O12 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
O10 C38 C28 127.5(5) . . ?
O10 C38 C39 113.3(4) . . ?
C28 C38 C39 119.2(4) . . ?
F9 C39 F7 111.6(7) . . ?
F9 C39 F8 101.2(7) . . ?
F7 C39 F8 101.1(6) . . ?
F9 C39 C38 115.4(5) . . ?
F7 C39 C38 114.0(5) . . ?
F8 C39 C38 111.9(5) . . ?
O13 C40 H40A 109.5 . . ?
O13 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
O13 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
O5 Nd1 O1 110.78(13) . . ?
O5 Nd1 O2 75.37(12) . . ?
O1 Nd1 O2 71.34(11) . . ?
O5 Nd1 O10 80.37(12) . . ?
O1 Nd1 O10 144.01(11) . . ?
O2 Nd1 O10 79.30(12) . . ?
O5 Nd1 O6 72.51(13) . . ?
O1 Nd1 O6 75.91(12) . . ?
O2 Nd1 O6 121.13(13) . . ?
O10 Nd1 O6 138.85(11) . . ?
O5 Nd1 O9 75.64(12) . . ?
O1 Nd1 O9 144.41(11) . . ?
O2 Nd1 O9 141.06(11) . . ?
O10 Nd1 O9 70.69(11) . . ?
O6 Nd1 O9 72.94(11) . . ?
O5 Nd1 O14 145.86(12) . . ?
O1 Nd1 O14 78.96(13) . . ?
O2 Nd1 O14 77.41(12) . . ?
O10 Nd1 O14 74.65(12) . . ?
O6 Nd1 O14 140.58(13) . . ?
O9 Nd1 O14 116.11(12) . . ?
O5 Nd1 O13 141.41(12) . . ?
O1 Nd1 O13 78.04(13) . . ?
O2 Nd1 O13 139.87(12) . . ?
O10 Nd1 O13 115.20(14) . . ?
O6 Nd1 O13 73.72(14) . . ?
O9 Nd1 O13 77.08(12) . . ?
O14 Nd1 O13 71.69(13) . . ?
C1 O1 Nd1 135.1(3) . . ?
C10 O2 Nd1 136.8(3) . . ?
C7 O3 C13 116.6(4) . . ?
C6 O4 C12 118.2(5) . . ?
C14 O5 Nd1 132.0(4) . . ?
C25 O6 Nd1 132.6(3) . . ?
C19 O7 C23 117.9(5) . . ?
C20 O8 C24 116.7(5) . . ?
C27 O9 Nd1 124.2(3) . . ?
C38 O10 Nd1 126.1(3) . . ?
C33 O11 C36 118.0(4) . . ?
C32 O12 C37 118.1(4) . . ?
C40 O13 Nd1 128.4(4) . . ?
C40 O13 H131 96(5) . . ?
Nd1 O13 H131 128(5) . . ?
Nd1 O14 H142 113.1 . . ?
Nd1 O14 H141 128.4 . . ?
H142 O14 H141 104.9 . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O13 H131 O3 0.848(10) 2.121(14) 2.964(6) 173(7) 2_645
O14 H142 O12 0.79 2.08 2.853(5) 167.5 1_565
O14 H141 O10 0.94 2.11 2.971(5) 152.0 3_665
_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full 27.48
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max 1.362
_refine_diff_density_min -0.655
_refine_diff_density_rms 0.108
_database_code_depnum_ccdc_archive 'CCDC 931138'
#######################################################################
#
# 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_lwz05
#TrackingRef 'complex2.CIF'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C41 H40 Cl4 F9 O15 Yb'
_chemical_formula_sum 'C41 H40 Cl4 F9 O15 Yb'
_chemical_formula_weight 1258.57
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'
Yb Yb -0.3850 5.5486 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_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 11.777(2)
_cell_length_b 12.332(3)
_cell_length_c 18.168(4)
_cell_angle_alpha 78.47(3)
_cell_angle_beta 88.87(3)
_cell_angle_gamma 70.05(3)
_cell_volume 2426.8(9)
_cell_formula_units_Z 2
_cell_measurement_temperature 293(2)
_cell_measurement_reflns_used 18635
_cell_measurement_theta_min 3.01
_cell_measurement_theta_max 27.45
_exptl_crystal_description block
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.42
_exptl_crystal_size_mid 0.22
_exptl_crystal_size_min 0.21
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.722
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1250
_exptl_absorpt_coefficient_mu 2.246
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.4500
_exptl_absorpt_correction_T_max 0.6450
_exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 293(2)
_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 'Rigaku RAXIS-RAPID'
_diffrn_measurement_method '\w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time 0
_diffrn_standards_decay_% 0
_diffrn_reflns_number 22968
_diffrn_reflns_av_R_equivalents 0.0541
_diffrn_reflns_av_sigmaI/netI 0.0771
_diffrn_reflns_limit_h_min -13
_diffrn_reflns_limit_h_max 15
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_l_min -23
_diffrn_reflns_limit_l_max 23
_diffrn_reflns_theta_min 3.02
_diffrn_reflns_theta_max 27.45
_reflns_number_total 10739
_reflns_number_gt 8487
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'RAPID-AUTO (Rigaku 1998 RAPID-AUTO)'
_computing_cell_refinement 'RAPID-AUTO (Rigaku 1998 RAPID-AUTO)'
_computing_data_reduction 'CrystalClear (Rigaku/MSC, 2002)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)'
_computing_publication_material SHELXL-97
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0878P)^2^+3.9950P] where P=(Fo^2^+2Fc^2^)/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 10739
_refine_ls_number_parameters 607
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0765
_refine_ls_R_factor_gt 0.0564
_refine_ls_wR_factor_ref 0.1592
_refine_ls_wR_factor_gt 0.1425
_refine_ls_goodness_of_fit_ref 1.035
_refine_ls_restrained_S_all 1.035
_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
C1 C 0.7437(6) 0.3121(5) 0.1858(4) 0.0317(12) Uani 1 1 d . . .
C2 C 0.7464(6) 0.2159(5) 0.1503(4) 0.0360(14) Uani 1 1 d . . .
C3 C 0.8649(6) 0.1132(6) 0.1742(4) 0.0402(15) Uani 1 1 d . . .
H3A H 0.8501 0.0422 0.1989 0.048 Uiso 1 1 calc R . .
H3B H 0.9141 0.0971 0.1316 0.048 Uiso 1 1 calc R . .
C4 C 0.9239(7) 0.1595(6) 0.2288(4) 0.0411(15) Uani 1 1 d . . .
C5 C 1.0352(7) 0.1032(6) 0.2707(5) 0.0462(17) Uani 1 1 d . . .
H5 H 1.0850 0.0278 0.2669 0.055 Uiso 1 1 calc R . .
C6 C 1.0669(7) 0.1642(7) 0.3170(5) 0.0475(17) Uani 1 1 d . . .
C7 C 0.9958(7) 0.2785(7) 0.3244(4) 0.0425(16) Uani 1 1 d . . .
C8 C 0.8869(6) 0.3344(6) 0.2820(4) 0.0379(14) Uani 1 1 d . . .
H8 H 0.8374 0.4101 0.2854 0.045 Uiso 1 1 calc R . .
C9 C 0.8545(6) 0.2726(6) 0.2342(4) 0.0349(13) Uani 1 1 d . . .
C10 C 1.2554(10) 0.0071(10) 0.3579(8) 0.093(4) Uani 1 1 d . . .
H10A H 1.2185 -0.0509 0.3759 0.140 Uiso 1 1 calc R . .
H10B H 1.3276 -0.0098 0.3882 0.140 Uiso 1 1 calc R . .
H10C H 1.2757 0.0053 0.3066 0.140 Uiso 1 1 calc R . .
C11 C 0.9717(10) 0.4440(8) 0.3801(6) 0.073(3) Uani 1 1 d . . .
H11A H 0.9693 0.4976 0.3334 0.109 Uiso 1 1 calc R . .
H11B H 1.0084 0.4648 0.4193 0.109 Uiso 1 1 calc R . .
H11C H 0.8908 0.4483 0.3924 0.109 Uiso 1 1 calc R . .
C12 C 0.6518(6) 0.2284(5) 0.1025(4) 0.0353(14) Uani 1 1 d . . .
C13 C 0.6531(7) 0.1243(6) 0.0671(5) 0.0457(17) Uani 1 1 d . . .
C14 C 0.5540(6) 0.4126(6) 0.3301(4) 0.0357(14) Uani 1 1 d . . .
C15 C 0.5952(6) 0.2854(6) 0.3436(4) 0.0393(15) Uani 1 1 d . . .
C16 C 0.6729(7) 0.2332(7) 0.4169(4) 0.0454(16) Uani 1 1 d . . .
H16A H 0.6396 0.1833 0.4522 0.055 Uiso 1 1 calc R . .
H16B H 0.7554 0.1881 0.4080 0.055 Uiso 1 1 calc R . .
C17 C 0.6661(7) 0.3437(7) 0.4447(4) 0.0421(15) Uani 1 1 d . . .
C18 C 0.7162(8) 0.3506(7) 0.5119(4) 0.0488(18) Uani 1 1 d . . .
H18 H 0.7599 0.2827 0.5463 0.059 Uiso 1 1 calc R . .
C19 C 0.6990(8) 0.4609(7) 0.5260(4) 0.0484(18) Uani 1 1 d . . .
C20 C 0.6322(7) 0.5644(7) 0.4739(4) 0.0449(16) Uani 1 1 d . . .
C21 C 0.5839(7) 0.5570(6) 0.4076(4) 0.0413(15) Uani 1 1 d . . .
H21 H 0.5408 0.6244 0.3727 0.050 Uiso 1 1 calc R . .
C22 C 0.6018(6) 0.4435(6) 0.3943(4) 0.0396(15) Uani 1 1 d . . .
C23 C 0.7782(9) 0.3841(9) 0.6529(5) 0.066(3) Uani 1 1 d . . .
H23A H 0.7117 0.3579 0.6680 0.100 Uiso 1 1 calc R . .
H23B H 0.8058 0.4087 0.6940 0.100 Uiso 1 1 calc R . .
H23C H 0.8429 0.3207 0.6390 0.100 Uiso 1 1 calc R . .
C24 C 0.5631(10) 0.7739(7) 0.4442(6) 0.064(2) Uani 1 1 d . . .
H24A H 0.6093 0.7782 0.4002 0.096 Uiso 1 1 calc R . .
H24B H 0.5559 0.8395 0.4671 0.096 Uiso 1 1 calc R . .
H24C H 0.4840 0.7764 0.4301 0.096 Uiso 1 1 calc R . .
C25 C 0.5598(6) 0.2262(6) 0.2959(4) 0.0373(14) Uani 1 1 d . . .
C26 C 0.5862(8) 0.0946(7) 0.3205(5) 0.0506(18) Uani 1 1 d . . .
C27 C 0.2148(6) 0.6078(5) 0.0419(4) 0.0346(13) Uani 1 1 d . . .
C28 C 0.1804(6) 0.7101(6) 0.0756(4) 0.0372(14) Uani 1 1 d . . .
C29 C 0.0587(7) 0.7961(6) 0.0426(5) 0.0456(17) Uani 1 1 d . . .
H29A H 0.0649 0.8703 0.0162 0.055 Uiso 1 1 calc R . .
H29B H 0.0005 0.8110 0.0811 0.055 Uiso 1 1 calc R . .
C30 C 0.0246(6) 0.7317(6) -0.0113(4) 0.0409(15) Uani 1 1 d . . .
C31 C -0.0825(7) 0.7685(7) -0.0556(5) 0.0456(17) Uani 1 1 d . . .
H31 H -0.1428 0.8407 -0.0555 0.055 Uiso 1 1 calc R . .
C32 C -0.0961(7) 0.6938(7) -0.1000(4) 0.0433(16) Uani 1 1 d . . .
C33 C -0.0016(7) 0.5847(6) -0.1013(4) 0.0397(15) Uani 1 1 d . . .
C34 C 0.1036(6) 0.5503(6) -0.0582(4) 0.0369(14) Uani 1 1 d . . .
H34 H 0.1653 0.4795 -0.0594 0.044 Uiso 1 1 calc R . .
C35 C 0.1157(6) 0.6254(6) -0.0119(4) 0.0349(13) Uani 1 1 d . . .
C36 C -0.2977(9) 0.8198(9) -0.1422(7) 0.083(3) Uani 1 1 d . . .
H36A H -0.3243 0.8149 -0.0917 0.124 Uiso 1 1 calc R . .
H36B H -0.3619 0.8243 -0.1757 0.124 Uiso 1 1 calc R . .
H36C H -0.2757 0.8889 -0.1568 0.124 Uiso 1 1 calc R . .
C37 C 0.0599(8) 0.4147(8) -0.1563(5) 0.058(2) Uani 1 1 d . . .
H37A H 0.1319 0.4300 -0.1728 0.087 Uiso 1 1 calc R . .
H37B H 0.0318 0.3819 -0.1929 0.087 Uiso 1 1 calc R . .
H37C H 0.0774 0.3598 -0.1089 0.087 Uiso 1 1 calc R . .
C38 C 0.2534(6) 0.7226(6) 0.1298(4) 0.0384(14) Uani 1 1 d . . .
C39 C 0.2095(8) 0.8343(7) 0.1625(5) 0.052(2) Uani 1 1 d . . .
C40 C 0.8712(19) 0.8328(18) 0.4607(12) 0.156(7) Uiso 1 1 d . . .
H40A H 0.8886 0.7924 0.5130 0.187 Uiso 1 1 calc R . .
H40B H 0.7882 0.8868 0.4555 0.187 Uiso 1 1 calc R . .
C41 C 0.5896(19) 0.7658(19) 0.1484(12) 0.154(7) Uiso 1 1 d . . .
H41A H 0.5717 0.6944 0.1491 0.184 Uiso 1 1 calc R . .
H41B H 0.5130 0.8306 0.1428 0.184 Uiso 1 1 calc R . .
Cl1 Cl 0.9679(8) 0.9108(7) 0.4352(5) 0.220(3) Uiso 1 1 d . . .
Cl2 Cl 0.8875(8) 0.7363(8) 0.4072(5) 0.223(3) Uiso 1 1 d . . .
Cl3 Cl 0.6629(6) 0.7521(6) 0.2392(4) 0.174(2) Uiso 1 1 d . . .
Cl4 Cl 0.6636(4) 0.7870(4) 0.0775(2) 0.1146(11) Uiso 1 1 d . . .
Yb1 Yb 0.45861(2) 0.45734(2) 0.156559(15) 0.03032(10) Uani 1 1 d . . .
F1 F 0.5819(7) 0.0711(5) 0.1022(4) 0.095(2) Uani 1 1 d . . .
F2 F 0.6115(6) 0.1609(5) -0.0041(3) 0.085(2) Uani 1 1 d . . .
F3 F 0.7604(5) 0.0434(5) 0.0659(4) 0.0785(18) Uani 1 1 d . . .
F4 F 0.5282(8) 0.0545(5) 0.2790(4) 0.118(3) Uani 1 1 d . . .
F5 F 0.7033(7) 0.0352(5) 0.3178(6) 0.117(3) Uani 1 1 d . . .
F6 F 0.5610(8) 0.0602(6) 0.3903(4) 0.102(2) Uani 1 1 d . . .
F7 F 0.2883(6) 0.8419(6) 0.2079(5) 0.110(3) Uani 1 1 d . . .
F8 F 0.1138(7) 0.8355(6) 0.2047(4) 0.102(2) Uani 1 1 d . . .
F9 F 0.1664(7) 0.9335(4) 0.1123(4) 0.092(2) Uani 1 1 d . . .
O1 O 0.6635(4) 0.4114(4) 0.1794(3) 0.0363(10) Uani 1 1 d . . .
O2 O 0.5549(4) 0.3173(4) 0.0850(3) 0.0370(10) Uani 1 1 d . . .
O3 O 1.1740(5) 0.1199(5) 0.3620(4) 0.0643(17) Uani 1 1 d . . .
O4 O 1.0406(5) 0.3271(5) 0.3729(4) 0.0584(15) Uani 1 1 d . . .
O5 O 0.5015(4) 0.2734(4) 0.2329(3) 0.0387(10) Uani 1 1 d . . .
O6 O 0.4899(4) 0.4846(4) 0.2758(3) 0.0372(10) Uani 1 1 d . . .
O7 O 0.7397(6) 0.4806(6) 0.5903(3) 0.0631(16) Uani 1 1 d . . .
O8 O 0.6223(6) 0.6676(5) 0.4958(3) 0.0611(16) Uani 1 1 d . . .
O9 O 0.3548(4) 0.6510(4) 0.1576(3) 0.0405(11) Uani 1 1 d . . .
O10 O 0.3090(4) 0.5185(4) 0.0564(3) 0.0356(10) Uani 1 1 d . . .
O11 O -0.1951(5) 0.7172(5) -0.1456(4) 0.0584(15) Uani 1 1 d . . .
O12 O -0.0320(5) 0.5229(5) -0.1479(3) 0.0530(13) Uani 1 1 d . . .
O13 O 0.5364(5) 0.5686(4) 0.0609(3) 0.0400(10) Uani 1 1 d . . .
H131 H 0.5003 0.6229 0.0240 0.060 Uiso 1 1 d R . .
H132 H 0.6071 0.5316 0.0491 0.060 Uiso 1 1 d R . .
O14 O 0.2784(4) 0.4428(4) 0.2087(3) 0.0403(11) Uani 1 1 d . . .
H141 H 0.2592 0.5166 0.2042 0.060 Uiso 1 1 d R . .
H142 H 0.2187 0.4242 0.1975 0.060 Uiso 1 1 d R . .
O15 O 0.3033(6) 0.3004(6) 0.3518(3) 0.0623(16) Uani 1 1 d . . .
H151 H 0.2571 0.3679 0.3567 0.093 Uiso 1 1 d R . .
H152 H 0.2649 0.2522 0.3613 0.093 Uiso 1 1 d R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.027(3) 0.029(3) 0.033(3) -0.006(2) 0.003(2) -0.003(3)
C2 0.033(3) 0.026(3) 0.042(4) -0.009(3) -0.001(3) 0.000(3)
C3 0.035(3) 0.034(3) 0.044(4) -0.013(3) 0.000(3) 0.000(3)
C4 0.041(4) 0.043(4) 0.035(4) -0.007(3) 0.000(3) -0.009(3)
C5 0.038(4) 0.036(3) 0.055(5) -0.006(3) -0.008(3) -0.001(3)
C6 0.031(4) 0.046(4) 0.055(5) -0.002(3) -0.008(3) -0.005(3)
C7 0.039(4) 0.046(4) 0.043(4) -0.006(3) -0.003(3) -0.016(3)
C8 0.028(3) 0.036(3) 0.046(4) -0.008(3) 0.004(3) -0.006(3)
C9 0.025(3) 0.030(3) 0.043(4) -0.002(3) 0.000(3) -0.003(3)
C10 0.060(6) 0.071(7) 0.120(11) -0.013(7) -0.043(7) 0.013(5)
C11 0.074(6) 0.053(5) 0.094(8) -0.030(5) -0.021(6) -0.014(5)
C12 0.036(3) 0.027(3) 0.039(4) -0.010(3) -0.002(3) -0.004(3)
C13 0.040(4) 0.030(3) 0.061(5) -0.015(3) -0.010(3) -0.001(3)
C14 0.034(3) 0.038(3) 0.032(3) -0.009(3) -0.001(3) -0.006(3)
C15 0.043(4) 0.041(4) 0.030(3) -0.004(3) -0.007(3) -0.011(3)
C16 0.049(4) 0.046(4) 0.034(4) -0.004(3) -0.009(3) -0.009(3)
C17 0.051(4) 0.044(4) 0.030(3) -0.004(3) -0.006(3) -0.016(3)
C18 0.058(5) 0.051(4) 0.030(4) 0.001(3) -0.013(3) -0.014(4)
C19 0.057(5) 0.056(4) 0.032(4) -0.009(3) -0.010(3) -0.018(4)
C20 0.046(4) 0.043(4) 0.045(4) -0.015(3) 0.001(3) -0.012(3)
C21 0.044(4) 0.037(3) 0.035(4) -0.009(3) -0.007(3) -0.004(3)
C22 0.038(4) 0.046(4) 0.032(3) -0.007(3) -0.005(3) -0.010(3)
C23 0.074(6) 0.075(6) 0.035(4) -0.012(4) -0.017(4) -0.004(5)
C24 0.087(7) 0.041(4) 0.065(6) -0.014(4) -0.004(5) -0.020(5)
C25 0.032(3) 0.036(3) 0.040(4) -0.004(3) -0.002(3) -0.008(3)
C26 0.055(5) 0.035(4) 0.050(5) 0.000(3) -0.012(4) -0.005(4)
C27 0.036(3) 0.029(3) 0.036(3) -0.002(3) -0.006(3) -0.010(3)
C28 0.037(4) 0.030(3) 0.041(4) -0.009(3) -0.008(3) -0.005(3)
C29 0.037(4) 0.032(3) 0.061(5) -0.011(3) -0.009(3) -0.002(3)
C30 0.039(4) 0.040(4) 0.042(4) -0.004(3) -0.007(3) -0.013(3)
C31 0.036(4) 0.041(4) 0.054(5) -0.002(3) -0.012(3) -0.011(3)
C32 0.040(4) 0.050(4) 0.037(4) 0.006(3) -0.012(3) -0.019(3)
C33 0.047(4) 0.045(4) 0.032(3) -0.004(3) -0.003(3) -0.025(3)
C34 0.033(3) 0.039(3) 0.040(4) -0.008(3) 0.000(3) -0.014(3)
C35 0.033(3) 0.038(3) 0.032(3) 0.002(3) -0.005(3) -0.015(3)
C36 0.060(6) 0.071(7) 0.096(9) -0.012(6) -0.038(6) 0.004(5)
C37 0.063(5) 0.060(5) 0.057(5) -0.022(4) -0.003(4) -0.025(5)
C38 0.042(4) 0.028(3) 0.041(4) -0.009(3) -0.001(3) -0.005(3)
C39 0.057(5) 0.041(4) 0.052(5) -0.018(4) -0.016(4) -0.002(4)
Yb1 0.03126(16) 0.02628(14) 0.02955(15) -0.00582(10) -0.00687(10) -0.00449(11)
F1 0.116(5) 0.067(4) 0.133(6) -0.051(4) 0.048(5) -0.056(4)
F2 0.121(5) 0.059(3) 0.067(4) -0.027(3) -0.037(3) -0.011(3)
F3 0.058(3) 0.063(3) 0.112(5) -0.054(3) -0.014(3) 0.004(3)
F4 0.195(8) 0.050(3) 0.112(6) 0.010(3) -0.086(6) -0.055(5)
F5 0.098(5) 0.043(3) 0.178(8) 0.001(4) 0.014(5) 0.003(3)
F6 0.181(8) 0.063(4) 0.068(4) 0.005(3) 0.017(4) -0.060(5)
F7 0.086(4) 0.075(4) 0.159(7) -0.081(5) -0.059(4) 0.020(3)
F8 0.123(6) 0.086(4) 0.099(5) -0.054(4) 0.042(5) -0.020(4)
F9 0.154(6) 0.032(2) 0.074(4) -0.010(2) -0.024(4) -0.008(3)
O1 0.037(3) 0.027(2) 0.040(3) -0.0045(19) -0.006(2) -0.0053(19)
O2 0.042(3) 0.030(2) 0.034(2) -0.0088(19) -0.009(2) -0.005(2)
O3 0.039(3) 0.055(3) 0.085(5) -0.014(3) -0.033(3) 0.003(3)
O4 0.052(3) 0.054(3) 0.067(4) -0.017(3) -0.025(3) -0.012(3)
O5 0.040(3) 0.035(2) 0.038(3) -0.005(2) -0.006(2) -0.010(2)
O6 0.039(3) 0.033(2) 0.032(2) -0.0072(19) -0.0110(19) -0.003(2)
O7 0.084(4) 0.063(4) 0.042(3) -0.012(3) -0.021(3) -0.024(3)
O8 0.085(4) 0.048(3) 0.052(3) -0.016(3) -0.014(3) -0.020(3)
O9 0.040(3) 0.031(2) 0.043(3) -0.010(2) -0.012(2) 0.000(2)
O10 0.030(2) 0.028(2) 0.042(3) -0.0085(19) -0.0074(19) -0.0007(19)
O11 0.047(3) 0.059(3) 0.067(4) -0.004(3) -0.023(3) -0.019(3)
O12 0.053(3) 0.057(3) 0.054(3) -0.013(3) -0.017(3) -0.022(3)
O13 0.046(3) 0.034(2) 0.036(3) -0.004(2) -0.004(2) -0.011(2)
O14 0.033(2) 0.042(3) 0.046(3) -0.011(2) -0.005(2) -0.012(2)
O15 0.066(4) 0.076(4) 0.058(4) -0.020(3) 0.007(3) -0.037(4)
_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
C1 O1 1.250(7) . ?
C1 C2 1.451(8) . ?
C1 C9 1.467(9) . ?
C2 C12 1.374(9) . ?
C2 C3 1.529(9) . ?
C3 C4 1.522(9) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C9 1.377(9) . ?
C4 C5 1.409(10) . ?
C5 C6 1.368(11) . ?
C5 H5 0.9300 . ?
C6 O3 1.396(9) . ?
C6 C7 1.404(11) . ?
C7 O4 1.364(8) . ?
C7 C8 1.391(10) . ?
C8 C9 1.399(9) . ?
C8 H8 0.9300 . ?
C10 O3 1.410(12) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 O4 1.423(10) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 O2 1.276(8) . ?
C12 C13 1.541(8) . ?
C13 F1 1.314(10) . ?
C13 F3 1.319(9) . ?
C13 F2 1.326(10) . ?
C14 O6 1.246(8) . ?
C14 C15 1.445(9) . ?
C14 C22 1.474(9) . ?
C15 C25 1.391(9) . ?
C15 C16 1.526(9) . ?
C16 C17 1.522(10) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C22 1.367(10) . ?
C17 C18 1.396(9) . ?
C18 C19 1.381(11) . ?
C18 H18 0.9300 . ?
C19 O7 1.368(8) . ?
C19 C20 1.416(11) . ?
C20 C21 1.374(10) . ?
C20 O8 1.375(8) . ?
C21 C22 1.412(9) . ?
C21 H21 0.9300 . ?
C23 O7 1.423(11) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 O8 1.413(11) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 O5 1.269(8) . ?
C25 C26 1.517(10) . ?
C26 F4 1.296(9) . ?
C26 F6 1.317(10) . ?
C26 F5 1.327(11) . ?
C27 O10 1.256(8) . ?
C27 C28 1.443(9) . ?
C27 C35 1.467(8) . ?
C28 C38 1.385(9) . ?
C28 C29 1.511(9) . ?
C29 C30 1.515(9) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C35 1.385(10) . ?
C30 C31 1.396(9) . ?
C31 C32 1.388(10) . ?
C31 H31 0.9300 . ?
C32 O11 1.357(8) . ?
C32 C33 1.428(11) . ?
C33 C34 1.369(9) . ?
C33 O12 1.372(8) . ?
C34 C35 1.410(9) . ?
C34 H34 0.9300 . ?
C36 O11 1.431(12) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 O12 1.437(10) . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 O9 1.259(8) . ?
C38 C39 1.532(9) . ?
C39 F7 1.293(9) . ?
C39 F9 1.317(10) . ?
C39 F8 1.349(11) . ?
C40 Cl2 1.643(19) . ?
C40 Cl1 1.728(19) . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C41 Cl4 1.57(2) . ?
C41 Cl3 1.83(2) . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
Yb1 O9 2.285(5) . ?
Yb1 O5 2.305(5) . ?
Yb1 O1 2.309(5) . ?
Yb1 O6 2.313(4) . ?
Yb1 O2 2.337(4) . ?
Yb1 O14 2.356(5) . ?
Yb1 O13 2.363(5) . ?
Yb1 O10 2.378(4) . ?
Yb1 H141 2.4086 . ?
O13 H131 0.8469 . ?
O13 H132 0.8489 . ?
O14 H141 0.8469 . ?
O14 H142 0.8500 . ?
O15 H151 0.8460 . ?
O15 H152 0.8519 . ?
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 C1 C2 128.5(6) . . ?
O1 C1 C9 123.9(6) . . ?
C2 C1 C9 107.6(5) . . ?
C12 C2 C1 120.0(6) . . ?
C12 C2 C3 130.8(6) . . ?
C1 C2 C3 109.2(5) . . ?
C4 C3 C2 101.9(5) . . ?
C4 C3 H3A 111.4 . . ?
C2 C3 H3A 111.4 . . ?
C4 C3 H3B 111.4 . . ?
C2 C3 H3B 111.4 . . ?
H3A C3 H3B 109.2 . . ?
C9 C4 C5 119.6(6) . . ?
C9 C4 C3 111.6(6) . . ?
C5 C4 C3 128.9(7) . . ?
C6 C5 C4 117.2(7) . . ?
C6 C5 H5 121.4 . . ?
C4 C5 H5 121.4 . . ?
C5 C6 O3 123.7(7) . . ?
C5 C6 C7 123.8(7) . . ?
O3 C6 C7 112.5(7) . . ?
O4 C7 C8 124.7(7) . . ?
O4 C7 C6 116.5(7) . . ?
C8 C7 C6 118.8(6) . . ?
C7 C8 C9 117.5(6) . . ?
C7 C8 H8 121.2 . . ?
C9 C8 H8 121.2 . . ?
C4 C9 C8 123.0(6) . . ?
C4 C9 C1 109.6(6) . . ?
C8 C9 C1 127.3(6) . . ?
O3 C10 H10A 109.5 . . ?
O3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O4 C11 H11A 109.5 . . ?
O4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 C2 127.4(5) . . ?
O2 C12 C13 112.7(6) . . ?
C2 C12 C13 119.7(6) . . ?
F1 C13 F3 107.6(7) . . ?
F1 C13 F2 106.3(7) . . ?
F3 C13 F2 105.1(7) . . ?
F1 C13 C12 110.7(7) . . ?
F3 C13 C12 115.4(6) . . ?
F2 C13 C12 111.3(6) . . ?
O6 C14 C15 128.1(6) . . ?
O6 C14 C22 125.3(6) . . ?
C15 C14 C22 106.6(6) . . ?
C25 C15 C14 121.8(6) . . ?
C25 C15 C16 128.2(6) . . ?
C14 C15 C16 109.9(6) . . ?
C17 C16 C15 101.7(6) . . ?
C17 C16 H16A 111.4 . . ?
C15 C16 H16A 111.4 . . ?
C17 C16 H16B 111.4 . . ?
C15 C16 H16B 111.4 . . ?
H16A C16 H16B 109.3 . . ?
C22 C17 C18 120.9(7) . . ?
C22 C17 C16 111.3(6) . . ?
C18 C17 C16 127.8(7) . . ?
C19 C18 C17 118.2(7) . . ?
C19 C18 H18 120.9 . . ?
C17 C18 H18 120.9 . . ?
O7 C19 C18 124.3(7) . . ?
O7 C19 C20 114.6(7) . . ?
C18 C19 C20 121.1(6) . . ?
C21 C20 O8 125.2(7) . . ?
C21 C20 C19 120.4(6) . . ?
O8 C20 C19 114.4(6) . . ?
C20 C21 C22 117.8(7) . . ?
C20 C21 H21 121.1 . . ?
C22 C21 H21 121.1 . . ?
C17 C22 C21 121.7(6) . . ?
C17 C22 C14 110.3(6) . . ?
C21 C22 C14 128.0(6) . . ?
O7 C23 H23A 109.5 . . ?
O7 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O7 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O8 C24 H24A 109.5 . . ?
O8 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O8 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O5 C25 C15 125.6(6) . . ?
O5 C25 C26 115.2(6) . . ?
C15 C25 C26 119.2(6) . . ?
F4 C26 F6 105.9(8) . . ?
F4 C26 F5 107.3(8) . . ?
F6 C26 F5 104.3(8) . . ?
F4 C26 C25 113.0(7) . . ?
F6 C26 C25 114.8(7) . . ?
F5 C26 C25 110.9(7) . . ?
O10 C27 C28 127.6(6) . . ?
O10 C27 C35 125.6(6) . . ?
C28 C27 C35 106.8(6) . . ?
C38 C28 C27 122.3(6) . . ?
C38 C28 C29 127.5(6) . . ?
C27 C28 C29 110.2(5) . . ?
C28 C29 C30 102.2(5) . . ?
C28 C29 H29A 111.3 . . ?
C30 C29 H29A 111.3 . . ?
C28 C29 H29B 111.3 . . ?
C30 C29 H29B 111.3 . . ?
H29A C29 H29B 109.2 . . ?
C35 C30 C31 121.7(6) . . ?
C35 C30 C29 110.9(6) . . ?
C31 C30 C29 127.4(7) . . ?
C32 C31 C30 117.7(7) . . ?
C32 C31 H31 121.1 . . ?
C30 C31 H31 121.1 . . ?
O11 C32 C31 124.4(7) . . ?
O11 C32 C33 115.0(6) . . ?
C31 C32 C33 120.6(6) . . ?
C34 C33 O12 126.9(7) . . ?
C34 C33 C32 121.1(6) . . ?
O12 C33 C32 112.0(6) . . ?
C33 C34 C35 118.1(7) . . ?
C33 C34 H34 121.0 . . ?
C35 C34 H34 121.0 . . ?
C30 C35 C34 120.8(6) . . ?
C30 C35 C27 109.8(6) . . ?
C34 C35 C27 129.4(6) . . ?
O11 C36 H36A 109.5 . . ?
O11 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
O11 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
O12 C37 H37A 109.5 . . ?
O12 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
O12 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
O9 C38 C28 127.6(6) . . ?
O9 C38 C39 113.7(6) . . ?
C28 C38 C39 118.7(6) . . ?
F7 C39 F9 109.8(7) . . ?
F7 C39 F8 104.3(8) . . ?
F9 C39 F8 102.5(8) . . ?
F7 C39 C38 113.8(7) . . ?
F9 C39 C38 114.9(7) . . ?
F8 C39 C38 110.3(7) . . ?
Cl2 C40 Cl1 110.1(13) . . ?
Cl2 C40 H40A 109.6 . . ?
Cl1 C40 H40A 109.6 . . ?
Cl2 C40 H40B 109.6 . . ?
Cl1 C40 H40B 109.6 . . ?
H40A C40 H40B 108.2 . . ?
Cl4 C41 Cl3 115.9(12) . . ?
Cl4 C41 H41A 108.3 . . ?
Cl3 C41 H41A 108.3 . . ?
Cl4 C41 H41B 108.3 . . ?
Cl3 C41 H41B 108.3 . . ?
H41A C41 H41B 107.4 . . ?
O9 Yb1 O5 139.91(18) . . ?
O9 Yb1 O1 111.20(16) . . ?
O5 Yb1 O1 80.91(16) . . ?
O9 Yb1 O6 73.11(17) . . ?
O5 Yb1 O6 75.40(16) . . ?
O1 Yb1 O6 71.52(17) . . ?
O9 Yb1 O2 147.14(18) . . ?
O5 Yb1 O2 72.26(17) . . ?
O1 Yb1 O2 74.01(16) . . ?
O6 Yb1 O2 135.61(16) . . ?
O9 Yb1 O14 79.74(18) . . ?
O5 Yb1 O14 71.38(17) . . ?
O1 Yb1 O14 145.08(17) . . ?
O6 Yb1 O14 81.06(17) . . ?
O2 Yb1 O14 115.30(16) . . ?
O9 Yb1 O13 73.70(18) . . ?
O5 Yb1 O13 143.12(18) . . ?
O1 Yb1 O13 69.61(17) . . ?
O6 Yb1 O13 113.54(16) . . ?
O2 Yb1 O13 78.53(16) . . ?
O14 Yb1 O13 143.53(18) . . ?
O9 Yb1 O10 75.63(15) . . ?
O5 Yb1 O10 119.08(15) . . ?
O1 Yb1 O10 141.63(17) . . ?
O6 Yb1 O10 141.93(16) . . ?
O2 Yb1 O10 81.38(15) . . ?
O14 Yb1 O10 72.43(17) . . ?
O13 Yb1 O10 77.04(16) . . ?
O9 Yb1 H141 59.3 . . ?
O5 Yb1 H141 89.4 . . ?
O1 Yb1 H141 147.4 . . ?
O6 Yb1 H141 75.9 . . ?
O2 Yb1 H141 132.4 . . ?
O14 Yb1 H141 20.4 . . ?
O13 Yb1 H141 127.2 . . ?
O10 Yb1 H141 69.7 . . ?
C1 O1 Yb1 126.8(4) . . ?
C12 O2 Yb1 128.0(4) . . ?
C6 O3 C10 118.0(7) . . ?
C7 O4 C11 117.6(6) . . ?
C25 O5 Yb1 132.4(4) . . ?
C14 O6 Yb1 129.0(4) . . ?
C19 O7 C23 117.5(7) . . ?
C20 O8 C24 117.0(6) . . ?
C38 O9 Yb1 133.8(4) . . ?
C27 O10 Yb1 130.2(4) . . ?
C32 O11 C36 118.1(7) . . ?
C33 O12 C37 116.3(6) . . ?
Yb1 O13 H131 130.2 . . ?
Yb1 O13 H132 114.3 . . ?
H131 O13 H132 109.1 . . ?
Yb1 O14 H141 83.3 . . ?
Yb1 O14 H142 138.9 . . ?
H141 O14 H142 111.6 . . ?
H151 O15 H152 109.1 . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O15 H152 O4 0.85 2.50 3.022(8) 120.1 1_455
O15 H152 O3 0.85 2.23 3.073(8) 168.0 1_455
O15 H151 O7 0.85 2.28 2.973(8) 139.7 2_666
O14 H142 O11 0.85 2.24 2.906(7) 135.5 2_565
O14 H142 O12 0.85 2.22 2.987(7) 149.7 2_565
O14 H141 O9 0.85 2.32 2.976(7) 134.0 .
O13 H132 O10 0.85 2.24 2.905(7) 135.4 2_665
O13 H131 F2 0.85 2.49 3.156(8) 135.9 2_665
O13 H131 O2 0.85 2.01 2.785(7) 152.3 2_665
_diffrn_measured_fraction_theta_max 0.969
_diffrn_reflns_theta_full 27.45
_diffrn_measured_fraction_theta_full 0.969
_refine_diff_density_max 2.101
_refine_diff_density_min -1.750
_refine_diff_density_rms 0.154
_database_code_depnum_ccdc_archive 'CCDC 931139'
#######################################################################
#
# 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_a
#TrackingRef 'complex3.CIF'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C51 H38 F9 N2 Nd O12'
_chemical_formula_sum 'C51 H38 F9 N2 Nd O12'
_chemical_formula_weight 1186.07
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Nd Nd -0.1943 3.0179 '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 13.3522(5)
_cell_length_b 19.6431(9)
_cell_length_c 19.7333(5)
_cell_angle_alpha 90.00
_cell_angle_beta 106.942(3)
_cell_angle_gamma 90.00
_cell_volume 4951.0(3)
_cell_formula_units_Z 4
_cell_measurement_temperature 293(2)
_cell_measurement_reflns_used 2857
_cell_measurement_theta_min 3.1834
_cell_measurement_theta_max 27.5021
_exptl_crystal_description block
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.22
_exptl_crystal_size_mid 0.19
_exptl_crystal_size_min 0.16
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.591
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 2380
_exptl_absorpt_coefficient_mu 1.147
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.7864
_exptl_absorpt_correction_T_max 0.8377
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 293(2)
_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 'Xcalibur, Eos'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean 16.1954
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 18813
_diffrn_reflns_av_R_equivalents 0.0331
_diffrn_reflns_av_sigmaI/netI 0.0709
_diffrn_reflns_limit_h_min -17
_diffrn_reflns_limit_h_max 17
_diffrn_reflns_limit_k_min -5
_diffrn_reflns_limit_k_max 25
_diffrn_reflns_limit_l_min -25
_diffrn_reflns_limit_l_max 13
_diffrn_reflns_theta_min 3.19
_diffrn_reflns_theta_max 27.56
_reflns_number_total 11319
_reflns_number_gt 6845
_reflns_threshold_expression >2sigma(I)
_computing_data_collection ?
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics ?
_computing_publication_material ?
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0422P)^2^+7.0574P] where P=(Fo^2^+2Fc^2^)/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 11319
_refine_ls_number_parameters 676
_refine_ls_number_restraints 18
_refine_ls_R_factor_all 0.1091
_refine_ls_R_factor_gt 0.0575
_refine_ls_wR_factor_ref 0.1324
_refine_ls_wR_factor_gt 0.1113
_refine_ls_goodness_of_fit_ref 1.033
_refine_ls_restrained_S_all 1.075
_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
C1 C 0.4355(6) 0.7343(6) 0.1741(4) 0.086(3) Uani 1 1 d U . .
C2 C 0.5063(5) 0.7379(4) 0.2497(3) 0.0562(19) Uani 1 1 d . . .
C3 C 0.4771(4) 0.7054(4) 0.3021(3) 0.0478(15) Uani 1 1 d . . .
C4 C 0.5446(4) 0.7036(3) 0.3740(3) 0.0406(13) Uani 1 1 d . . .
C5 C 0.4912(4) 0.6642(3) 0.4157(3) 0.0407(14) Uani 1 1 d . . .
C6 C 0.5272(5) 0.6452(3) 0.4870(3) 0.0468(15) Uani 1 1 d . . .
H6 H 0.5928 0.6590 0.5152 0.056 Uiso 1 1 calc R . .
C7 C 0.4646(5) 0.6061(3) 0.5143(3) 0.0502(16) Uani 1 1 d . . .
C8 C 0.3628(5) 0.5869(3) 0.4711(3) 0.0525(16) Uani 1 1 d . . .
C9 C 0.3291(5) 0.6048(3) 0.4010(3) 0.0537(17) Uani 1 1 d . . .
H9 H 0.2640 0.5908 0.3724 0.064 Uiso 1 1 calc R . .
C10 C 0.3941(4) 0.6442(3) 0.3733(3) 0.0453(15) Uani 1 1 d . . .
C11 C 0.5921(6) 0.5947(4) 0.6270(3) 0.079(2) Uani 1 1 d . . .
H11A H 0.6001 0.5747 0.6727 0.118 Uiso 1 1 calc R . .
H11B H 0.6031 0.6430 0.6321 0.118 Uiso 1 1 calc R . .
H11C H 0.6424 0.5752 0.6064 0.118 Uiso 1 1 calc R . .
C12 C 0.2044(6) 0.5296(5) 0.4664(4) 0.088(3) Uani 1 1 d . . .
H12A H 0.1733 0.5039 0.4964 0.132 Uiso 1 1 calc R . .
H12B H 0.2082 0.5018 0.4271 0.132 Uiso 1 1 calc R . .
H12C H 0.1625 0.5691 0.4490 0.132 Uiso 1 1 calc R . .
C13 C 0.8975(6) 0.9377(4) 0.2480(3) 0.0590(18) Uani 1 1 d . . .
C14 C 0.8765(5) 0.8973(3) 0.3086(3) 0.0413(13) Uani 1 1 d . . .
C15 C 0.9411(4) 0.9041(3) 0.3769(3) 0.0385(13) Uani 1 1 d . . .
C16 C 0.9186(4) 0.8691(3) 0.4347(3) 0.0369(13) Uani 1 1 d . . .
C17 C 1.0012(4) 0.8875(3) 0.4996(3) 0.0356(12) Uani 1 1 d . . .
C18 C 1.0136(4) 0.8658(3) 0.5694(3) 0.0398(13) Uani 1 1 d . . .
H18 H 0.9651 0.8370 0.5801 0.048 Uiso 1 1 calc R . .
C19 C 1.1000(4) 0.8887(3) 0.6215(3) 0.0444(14) Uani 1 1 d . . .
C20 C 1.1733(4) 0.9321(3) 0.6037(3) 0.0486(15) Uani 1 1 d . . .
C21 C 1.1605(4) 0.9517(3) 0.5348(3) 0.0480(15) Uani 1 1 d . . .
H21 H 1.2096 0.9796 0.5235 0.058 Uiso 1 1 calc R . .
C22 C 1.0727(4) 0.9291(3) 0.4824(3) 0.0390(13) Uani 1 1 d . . .
C23 C 1.0397(6) 0.8453(4) 0.7143(3) 0.069(2) Uani 1 1 d . . .
H23A H 1.0641 0.8367 0.7643 0.104 Uiso 1 1 calc R . .
H23B H 1.0174 0.8034 0.6896 0.104 Uiso 1 1 calc R . .
H23C H 0.9818 0.8765 0.7044 0.104 Uiso 1 1 calc R . .
C24 C 1.3312(6) 0.9958(5) 0.6472(4) 0.103(3) Uani 1 1 d . . .
H24A H 1.3836 1.0056 0.6910 0.154 Uiso 1 1 calc R . .
H24B H 1.2979 1.0374 0.6269 0.154 Uiso 1 1 calc R . .
H24C H 1.3634 0.9747 0.6150 0.154 Uiso 1 1 calc R . .
C25 C 0.9790(5) 0.6494(4) 0.5435(3) 0.0581(18) Uani 1 1 d . . .
C26 C 0.9571(5) 0.6844(3) 0.4713(3) 0.0440(14) Uani 1 1 d . . .
C27 C 1.0377(4) 0.7149(3) 0.4530(3) 0.0404(13) Uani 1 1 d . . .
C28 C 1.0240(4) 0.7410(3) 0.3832(3) 0.0365(13) Uani 1 1 d . . .
C29 C 1.1241(4) 0.7682(3) 0.3804(3) 0.0378(14) Uani 1 1 d . . .
C30 C 1.1481(4) 0.7993(3) 0.3236(3) 0.0424(14) Uani 1 1 d . . .
H30 H 1.0975 0.8038 0.2800 0.051 Uiso 1 1 calc R . .
C31 C 1.2478(4) 0.8233(3) 0.3332(3) 0.0462(15) Uani 1 1 d . . .
C32 C 1.3228(4) 0.8179(3) 0.4007(3) 0.0453(14) Uani 1 1 d . . .
C33 C 1.2976(4) 0.7872(3) 0.4564(3) 0.0490(15) Uani 1 1 d . . .
H33 H 1.3472 0.7838 0.5005 0.059 Uiso 1 1 calc R . .
C34 C 1.1973(4) 0.7614(3) 0.4460(3) 0.0422(14) Uani 1 1 d . . .
C35 C 1.2108(5) 0.8561(5) 0.2131(3) 0.081(3) Uani 1 1 d . . .
H35A H 1.2428 0.8787 0.1816 0.122 Uiso 1 1 calc R . .
H35B H 1.1495 0.8808 0.2148 0.122 Uiso 1 1 calc R . .
H35C H 1.1912 0.8107 0.1963 0.122 Uiso 1 1 calc R . .
C36 C 1.4947(5) 0.8470(4) 0.4702(3) 0.072(2) Uani 1 1 d . . .
H36A H 1.5573 0.8673 0.4648 0.108 Uiso 1 1 calc R . .
H36B H 1.5098 0.8016 0.4883 0.108 Uiso 1 1 calc R . .
H36C H 1.4695 0.8736 0.5026 0.108 Uiso 1 1 calc R . .
C37 C 0.6957(4) 0.5990(3) 0.2361(3) 0.0381(13) Uani 1 1 d . . .
C38 C 0.6822(5) 0.5815(3) 0.3485(3) 0.0486(15) Uani 1 1 d . . .
H38 H 0.6950 0.5963 0.3950 0.058 Uiso 1 1 calc R . .
C39 C 0.6380(5) 0.5180(3) 0.3316(4) 0.0565(17) Uani 1 1 d . . .
H39 H 0.6180 0.4919 0.3648 0.068 Uiso 1 1 calc R . .
C40 C 0.6247(5) 0.4948(3) 0.2644(4) 0.0603(18) Uani 1 1 d . . .
H40 H 0.5949 0.4522 0.2512 0.072 Uiso 1 1 calc R . .
C41 C 0.6557(5) 0.5349(3) 0.2150(3) 0.0469(15) Uani 1 1 d . . .
C42 C 0.6470(5) 0.5112(4) 0.1443(3) 0.0602(18) Uani 1 1 d . . .
H42 H 0.6205 0.4680 0.1300 0.072 Uiso 1 1 calc R . .
C43 C 0.6776(5) 0.5521(4) 0.0994(3) 0.0582(18) Uani 1 1 d . . .
H43 H 0.6737 0.5358 0.0545 0.070 Uiso 1 1 calc R . .
C44 C 0.7158(4) 0.6195(3) 0.1176(3) 0.0413(14) Uani 1 1 d . . .
C45 C 0.7427(4) 0.6628(4) 0.0709(3) 0.0483(17) Uani 1 1 d . . .
H45 H 0.7389 0.6483 0.0253 0.058 Uiso 1 1 calc R . .
C46 C 0.7746(4) 0.7267(4) 0.0922(3) 0.0495(17) Uani 1 1 d . . .
H46 H 0.7909 0.7570 0.0607 0.059 Uiso 1 1 calc R . .
C47 C 0.7830(4) 0.7471(4) 0.1611(3) 0.0497(15) Uani 1 1 d . . .
H47 H 0.8060 0.7911 0.1748 0.060 Uiso 1 1 calc R . .
C48 C 0.7256(4) 0.6434(3) 0.1868(3) 0.0361(13) Uani 1 1 d . . .
C49 C 1.1504(4) 0.7262(3) 0.4970(3) 0.0471(15) Uani 1 1 d . . .
H49A H 1.1541 0.7546 0.5379 0.057 Uiso 1 1 calc R . .
H49B H 1.1853 0.6833 0.5129 0.057 Uiso 1 1 calc R . .
C50 C 1.0413(4) 0.9444(3) 0.4046(3) 0.0432(14) Uani 1 1 d . . .
H50A H 1.0942 0.9292 0.3832 0.052 Uiso 1 1 calc R . .
H50B H 1.0291 0.9927 0.3957 0.052 Uiso 1 1 calc R . .
C51 C 0.3762(4) 0.6685(4) 0.2984(3) 0.0520(16) Uani 1 1 d . . .
H51A H 0.3165 0.6990 0.2842 0.062 Uiso 1 1 calc R . .
H51B H 0.3650 0.6306 0.2656 0.062 Uiso 1 1 calc R . .
F1 F 0.4163(5) 0.8007(5) 0.1513(4) 0.176(3) Uani 1 1 d U . .
F2 F 0.3431(4) 0.7160(4) 0.1623(2) 0.138(3) Uani 1 1 d . . .
F3 F 0.4791(5) 0.7181(5) 0.1309(3) 0.188(3) Uani 1 1 d U . .
F4 F 0.9734(5) 0.9816(3) 0.2657(2) 0.118(2) Uani 1 1 d . . .
F5 F 0.8176(4) 0.9705(4) 0.2114(3) 0.142(3) Uani 1 1 d . . .
F6 F 0.9218(6) 0.8975(3) 0.2031(3) 0.133(2) Uani 1 1 d . . .
F7 F 0.8961(4) 0.6212(3) 0.55412(19) 0.0923(16) Uani 1 1 d . . .
F8 F 1.0550(5) 0.6058(3) 0.5564(2) 0.126(2) Uani 1 1 d . . .
F9 F 1.0081(4) 0.6943(3) 0.59681(19) 0.0916(15) Uani 1 1 d . . .
N4 N 0.7082(3) 0.6235(3) 0.3027(2) 0.0414(11) Uani 1 1 d . . .
N5 N 0.7598(3) 0.7068(3) 0.2081(2) 0.0405(11) Uani 1 1 d . . .
Nd1 Nd 0.76376(2) 0.751263(19) 0.336021(13) 0.03616(10) Uani 1 1 d . . .
O1 O 0.5930(3) 0.7682(2) 0.25573(19) 0.0569(13) Uani 1 1 d . . .
O2 O 0.6347(3) 0.7289(2) 0.39786(18) 0.0449(11) Uani 1 1 d . . .
O3 O 0.4889(4) 0.5816(3) 0.5820(2) 0.0708(15) Uani 1 1 d . . .
O4 O 0.3062(4) 0.5501(3) 0.5054(2) 0.0751(15) Uani 1 1 d . . .
O5 O 0.7974(3) 0.8583(2) 0.28687(18) 0.0455(10) Uani 1 1 d . . .
O6 O 0.8428(3) 0.8303(2) 0.43269(17) 0.0413(9) Uani 1 1 d . . .
O7 O 1.1215(3) 0.8739(3) 0.69166(19) 0.0642(14) Uani 1 1 d . . .
O8 O 1.2550(3) 0.9509(3) 0.6602(2) 0.0730(15) Uani 1 1 d . . .
O9 O 0.8616(3) 0.6816(2) 0.43479(18) 0.0481(11) Uani 1 1 d . . .
O10 O 0.9415(3) 0.7423(2) 0.33157(16) 0.0398(9) Uani 1 1 d . . .
O11 O 1.2834(3) 0.8532(3) 0.2825(2) 0.0624(13) Uani 1 1 d . . .
O12 O 1.4173(3) 0.8447(3) 0.4035(2) 0.0606(13) Uani 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.059(4) 0.151(8) 0.044(4) 0.025(4) 0.010(3) -0.009(5)
C2 0.037(3) 0.093(6) 0.034(3) 0.011(3) 0.003(2) 0.002(4)
C3 0.038(3) 0.068(5) 0.036(3) 0.001(3) 0.008(2) 0.004(3)
C4 0.038(3) 0.049(4) 0.033(3) -0.006(3) 0.008(2) 0.000(3)
C5 0.037(3) 0.050(4) 0.035(3) -0.005(3) 0.011(2) -0.003(3)
C6 0.043(3) 0.057(4) 0.040(3) -0.006(3) 0.011(3) -0.013(3)
C7 0.053(4) 0.058(4) 0.041(3) 0.000(3) 0.017(3) -0.012(3)
C8 0.057(4) 0.051(4) 0.057(4) -0.009(3) 0.027(3) -0.019(3)
C9 0.041(3) 0.065(5) 0.056(4) -0.016(3) 0.015(3) -0.015(3)
C10 0.038(3) 0.057(4) 0.041(3) -0.008(3) 0.011(3) -0.008(3)
C11 0.076(5) 0.105(7) 0.049(4) 0.027(4) 0.010(4) -0.010(5)
C12 0.082(6) 0.102(7) 0.091(6) -0.023(5) 0.044(5) -0.050(5)
C13 0.084(5) 0.058(5) 0.031(3) 0.002(3) 0.010(3) -0.018(4)
C14 0.052(4) 0.034(3) 0.036(3) 0.002(3) 0.011(3) -0.003(3)
C15 0.046(3) 0.037(3) 0.033(3) -0.001(2) 0.012(2) -0.002(3)
C16 0.039(3) 0.040(3) 0.032(3) -0.003(2) 0.010(2) 0.000(3)
C17 0.035(3) 0.034(3) 0.035(3) -0.002(2) 0.007(2) 0.004(2)
C18 0.038(3) 0.046(4) 0.033(3) 0.000(3) 0.007(2) -0.001(3)
C19 0.040(3) 0.050(4) 0.038(3) -0.004(3) 0.003(2) -0.001(3)
C20 0.036(3) 0.057(4) 0.046(3) -0.011(3) 0.002(3) -0.006(3)
C21 0.038(3) 0.055(4) 0.049(3) -0.007(3) 0.009(3) -0.011(3)
C22 0.037(3) 0.038(3) 0.041(3) -0.001(3) 0.010(2) 0.002(3)
C23 0.080(5) 0.085(6) 0.038(3) 0.007(4) 0.010(3) -0.010(5)
C24 0.061(5) 0.147(10) 0.085(6) -0.014(6) -0.002(4) -0.054(6)
C25 0.058(4) 0.063(5) 0.043(4) 0.015(3) -0.001(3) -0.002(4)
C26 0.052(4) 0.044(4) 0.028(3) 0.000(3) -0.002(2) -0.001(3)
C27 0.036(3) 0.045(4) 0.033(3) 0.004(3) -0.001(2) -0.003(3)
C28 0.036(3) 0.038(4) 0.030(2) -0.003(2) 0.002(2) -0.001(3)
C29 0.033(3) 0.040(4) 0.034(3) -0.004(2) 0.000(2) 0.001(2)
C30 0.037(3) 0.046(4) 0.035(3) 0.002(3) -0.003(2) -0.002(3)
C31 0.039(3) 0.055(4) 0.041(3) -0.003(3) 0.006(3) -0.004(3)
C32 0.031(3) 0.048(4) 0.049(3) -0.004(3) -0.001(2) -0.007(3)
C33 0.035(3) 0.057(4) 0.042(3) -0.006(3) -0.010(2) 0.001(3)
C34 0.038(3) 0.045(4) 0.038(3) -0.002(3) 0.001(2) 0.001(3)
C35 0.061(5) 0.133(8) 0.040(3) 0.018(4) -0.002(3) -0.030(5)
C36 0.041(4) 0.087(6) 0.070(4) -0.003(4) -0.013(3) -0.012(4)
C37 0.031(3) 0.051(4) 0.028(3) -0.002(3) 0.003(2) 0.000(3)
C38 0.056(4) 0.050(4) 0.041(3) 0.004(3) 0.017(3) -0.001(3)
C39 0.065(4) 0.043(4) 0.066(4) 0.018(3) 0.027(3) -0.003(3)
C40 0.065(4) 0.039(4) 0.072(4) 0.000(3) 0.014(4) -0.011(3)
C41 0.046(3) 0.041(4) 0.051(3) -0.003(3) 0.010(3) -0.003(3)
C42 0.067(4) 0.048(4) 0.058(4) -0.016(3) 0.006(3) 0.005(4)
C43 0.065(4) 0.065(5) 0.042(3) -0.016(3) 0.011(3) 0.006(4)
C44 0.031(3) 0.057(4) 0.033(3) -0.006(3) 0.005(2) 0.004(3)
C45 0.033(3) 0.085(5) 0.027(3) -0.002(3) 0.009(2) 0.007(3)
C46 0.044(3) 0.074(5) 0.032(3) 0.005(3) 0.014(3) -0.009(3)
C47 0.049(3) 0.065(4) 0.035(3) 0.001(3) 0.012(2) -0.011(4)
C48 0.025(3) 0.052(4) 0.027(2) -0.003(3) 0.002(2) 0.003(3)
C49 0.049(3) 0.049(4) 0.034(3) 0.004(3) -0.003(2) 0.004(3)
C50 0.050(3) 0.039(4) 0.041(3) -0.002(3) 0.014(3) -0.007(3)
C51 0.040(3) 0.068(5) 0.043(3) -0.001(3) 0.003(3) -0.006(3)
F1 0.143(5) 0.209(7) 0.134(5) 0.087(5) -0.027(4) -0.030(5)
F2 0.077(3) 0.247(8) 0.058(3) 0.033(4) -0.028(2) -0.050(4)
F3 0.113(4) 0.378(9) 0.054(3) -0.062(4) -0.005(3) 0.049(5)
F4 0.172(5) 0.119(4) 0.054(2) 0.016(3) 0.018(3) -0.087(4)
F5 0.119(4) 0.184(7) 0.108(4) 0.104(4) 0.011(3) 0.016(4)
F6 0.266(7) 0.084(4) 0.093(3) -0.020(3) 0.123(4) -0.043(5)
F7 0.094(3) 0.118(4) 0.056(2) 0.035(3) 0.008(2) -0.033(3)
F8 0.175(5) 0.133(5) 0.091(3) 0.076(3) 0.072(4) 0.102(4)
F9 0.120(4) 0.101(4) 0.039(2) 0.004(2) 0.001(2) -0.013(3)
N4 0.042(3) 0.045(3) 0.034(2) 0.004(2) 0.007(2) -0.004(2)
N5 0.036(2) 0.053(3) 0.029(2) 0.001(2) 0.0058(19) -0.005(2)
Nd1 0.03406(15) 0.04856(18) 0.02328(13) -0.00034(15) 0.00432(10) -0.00762(16)
O1 0.040(2) 0.089(4) 0.038(2) 0.019(2) 0.0060(17) 0.000(2)
O2 0.037(2) 0.066(3) 0.0304(18) -0.0008(18) 0.0081(16) -0.0079(19)
O3 0.079(3) 0.087(4) 0.045(2) 0.010(3) 0.014(2) -0.031(3)
O4 0.076(3) 0.087(4) 0.069(3) -0.003(3) 0.032(3) -0.040(3)
O5 0.050(2) 0.052(3) 0.0311(19) 0.0044(18) 0.0056(17) -0.004(2)
O6 0.043(2) 0.051(3) 0.0301(18) -0.0042(18) 0.0095(16) -0.007(2)
O7 0.055(3) 0.095(4) 0.032(2) 0.009(2) -0.0043(19) -0.010(3)
O8 0.049(3) 0.100(4) 0.056(3) -0.003(3) -0.005(2) -0.020(3)
O9 0.044(2) 0.058(3) 0.037(2) 0.010(2) 0.0039(18) -0.012(2)
O10 0.0330(18) 0.054(3) 0.0275(16) -0.0005(18) 0.0009(14) -0.0025(19)
O11 0.043(2) 0.090(4) 0.046(2) 0.007(2) -0.0009(19) -0.026(2)
O12 0.034(2) 0.076(4) 0.058(3) 0.001(2) -0.0069(19) -0.014(2)
_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
C1 F3 1.206(9) . ?
C1 F2 1.240(8) . ?
C1 F1 1.379(12) . ?
C1 C2 1.518(9) . ?
C2 O1 1.276(7) . ?
C2 C3 1.364(8) . ?
C3 C4 1.444(7) . ?
C3 C51 1.513(8) . ?
C4 O2 1.260(6) . ?
C4 C5 1.459(8) . ?
C5 C10 1.379(7) . ?
C5 C6 1.399(7) . ?
C6 C7 1.357(8) . ?
C6 H6 0.9300 . ?
C7 O3 1.367(7) . ?
C7 C8 1.429(8) . ?
C8 O4 1.360(7) . ?
C8 C9 1.371(8) . ?
C9 C10 1.387(8) . ?
C9 H9 0.9300 . ?
C10 C51 1.505(8) . ?
C11 O3 1.427(8) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 O4 1.411(8) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 F5 1.276(8) . ?
C13 F6 1.296(8) . ?
C13 F4 1.298(8) . ?
C13 C14 1.527(8) . ?
C14 O5 1.275(6) . ?
C14 C15 1.379(7) . ?
C15 C16 1.437(7) . ?
C15 C50 1.513(7) . ?
C16 O6 1.259(6) . ?
C16 C17 1.471(7) . ?
C17 C22 1.372(7) . ?
C17 C18 1.404(7) . ?
C18 C19 1.377(7) . ?
C18 H18 0.9300 . ?
C19 O7 1.362(6) . ?
C19 C20 1.417(8) . ?
C20 O8 1.365(6) . ?
C20 C21 1.374(8) . ?
C21 C22 1.392(7) . ?
C21 H21 0.9300 . ?
C22 C50 1.500(7) . ?
C23 O7 1.412(7) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 O8 1.425(8) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 F8 1.295(8) . ?
C25 F7 1.309(7) . ?
C25 F9 1.339(8) . ?
C25 C26 1.531(8) . ?
C26 O9 1.270(6) . ?
C26 C27 1.369(8) . ?
C27 C28 1.430(7) . ?
C27 C49 1.518(7) . ?
C28 O10 1.264(6) . ?
C28 C29 1.456(7) . ?
C29 C34 1.383(7) . ?
C29 C30 1.393(7) . ?
C30 C31 1.372(7) . ?
C30 H30 0.9300 . ?
C31 O11 1.360(7) . ?
C31 C32 1.418(7) . ?
C32 O12 1.353(6) . ?
C32 C33 1.379(8) . ?
C33 C34 1.391(8) . ?
C33 H33 0.9300 . ?
C34 C49 1.500(8) . ?
C35 O11 1.429(7) . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C36 O12 1.417(7) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 N4 1.364(6) . ?
C37 C41 1.383(8) . ?
C37 C48 1.446(7) . ?
C38 N4 1.341(7) . ?
C38 C39 1.379(9) . ?
C38 H38 0.9300 . ?
C39 C40 1.364(9) . ?
C39 H39 0.9300 . ?
C40 C41 1.408(8) . ?
C40 H40 0.9300 . ?
C41 C42 1.442(8) . ?
C42 C43 1.346(9) . ?
C42 H42 0.9300 . ?
C43 C44 1.425(9) . ?
C43 H43 0.9300 . ?
C44 C45 1.376(8) . ?
C44 C48 1.415(7) . ?
C45 C46 1.353(9) . ?
C45 H45 0.9300 . ?
C46 C47 1.391(7) . ?
C46 H46 0.9300 . ?
C47 N5 1.323(7) . ?
C47 H47 0.9300 . ?
C48 N5 1.350(7) . ?
C49 H49A 0.9700 . ?
C49 H49B 0.9700 . ?
C50 H50A 0.9700 . ?
C50 H50B 0.9700 . ?
C51 H51A 0.9700 . ?
C51 H51B 0.9700 . ?
N4 Nd1 2.645(5) . ?
N5 Nd1 2.658(4) . ?
Nd1 O1 2.390(4) . ?
Nd1 O10 2.407(3) . ?
Nd1 O5 2.412(4) . ?
Nd1 O2 2.424(3) . ?
Nd1 O9 2.428(4) . ?
Nd1 O6 2.447(4) . ?
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
F3 C1 F2 116.8(9) . . ?
F3 C1 F1 95.8(8) . . ?
F2 C1 F1 97.6(8) . . ?
F3 C1 C2 114.6(7) . . ?
F2 C1 C2 119.8(6) . . ?
F1 C1 C2 106.3(8) . . ?
O1 C2 C3 126.8(5) . . ?
O1 C2 C1 113.6(5) . . ?
C3 C2 C1 119.3(6) . . ?
C2 C3 C4 121.4(5) . . ?
C2 C3 C51 129.4(5) . . ?
C4 C3 C51 109.1(5) . . ?
O2 C4 C3 127.8(5) . . ?
O2 C4 C5 124.7(5) . . ?
C3 C4 C5 107.4(5) . . ?
C10 C5 C6 121.4(5) . . ?
C10 C5 C4 109.7(5) . . ?
C6 C5 C4 128.9(5) . . ?
C7 C6 C5 118.6(5) . . ?
C7 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C6 C7 O3 126.0(5) . . ?
C6 C7 C8 120.1(5) . . ?
O3 C7 C8 113.9(5) . . ?
O4 C8 C9 124.9(6) . . ?
O4 C8 C7 114.4(5) . . ?
C9 C8 C7 120.6(5) . . ?
C8 C9 C10 118.8(6) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
C5 C10 C9 120.4(5) . . ?
C5 C10 C51 111.0(5) . . ?
C9 C10 C51 128.6(5) . . ?
O3 C11 H11A 109.5 . . ?
O3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
F5 C13 F6 104.8(6) . . ?
F5 C13 F4 106.0(7) . . ?
F6 C13 F4 104.9(7) . . ?
F5 C13 C14 113.1(6) . . ?
F6 C13 C14 111.0(6) . . ?
F4 C13 C14 116.2(5) . . ?
O5 C14 C15 127.4(5) . . ?
O5 C14 C13 111.9(5) . . ?
C15 C14 C13 120.7(5) . . ?
C14 C15 C16 121.0(5) . . ?
C14 C15 C50 129.7(5) . . ?
C16 C15 C50 109.3(4) . . ?
O6 C16 C15 128.1(5) . . ?
O6 C16 C17 124.7(5) . . ?
C15 C16 C17 107.2(5) . . ?
C22 C17 C18 122.1(5) . . ?
C22 C17 C16 109.3(5) . . ?
C18 C17 C16 128.5(5) . . ?
C19 C18 C17 117.8(5) . . ?
C19 C18 H18 121.1 . . ?
C17 C18 H18 121.1 . . ?
O7 C19 C18 124.9(5) . . ?
O7 C19 C20 115.1(5) . . ?
C18 C19 C20 120.0(5) . . ?
O8 C20 C21 124.8(6) . . ?
O8 C20 C19 113.9(5) . . ?
C21 C20 C19 121.2(5) . . ?
C20 C21 C22 118.7(6) . . ?
C20 C21 H21 120.7 . . ?
C22 C21 H21 120.7 . . ?
C17 C22 C21 120.2(5) . . ?
C17 C22 C50 111.4(5) . . ?
C21 C22 C50 128.4(5) . . ?
O7 C23 H23A 109.5 . . ?
O7 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O7 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O8 C24 H24A 109.5 . . ?
O8 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O8 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
F8 C25 F7 109.8(6) . . ?
F8 C25 F9 104.4(6) . . ?
F7 C25 F9 102.6(6) . . ?
F8 C25 C26 113.9(6) . . ?
F7 C25 C26 113.4(5) . . ?
F9 C25 C26 111.6(6) . . ?
O9 C26 C27 127.2(5) . . ?
O9 C26 C25 113.4(5) . . ?
C27 C26 C25 119.4(5) . . ?
C26 C27 C28 121.4(5) . . ?
C26 C27 C49 129.6(5) . . ?
C28 C27 C49 109.0(5) . . ?
O10 C28 C27 128.4(5) . . ?
O10 C28 C29 123.7(5) . . ?
C27 C28 C29 107.9(4) . . ?
C34 C29 C30 122.1(5) . . ?
C34 C29 C28 109.5(5) . . ?
C30 C29 C28 128.4(5) . . ?
C31 C30 C29 118.7(5) . . ?
C31 C30 H30 120.6 . . ?
C29 C30 H30 120.6 . . ?
O11 C31 C30 125.4(5) . . ?
O11 C31 C32 114.9(5) . . ?
C30 C31 C32 119.7(5) . . ?
O12 C32 C33 125.3(5) . . ?
O12 C32 C31 113.9(5) . . ?
C33 C32 C31 120.8(5) . . ?
C32 C33 C34 119.4(5) . . ?
C32 C33 H33 120.3 . . ?
C34 C33 H33 120.3 . . ?
C29 C34 C33 119.3(5) . . ?
C29 C34 C49 110.7(5) . . ?
C33 C34 C49 129.9(5) . . ?
O11 C35 H35A 109.5 . . ?
O11 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
O11 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
O12 C36 H36A 109.5 . . ?
O12 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
O12 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
N4 C37 C41 122.7(5) . . ?
N4 C37 C48 117.1(5) . . ?
C41 C37 C48 120.2(5) . . ?
N4 C38 C39 124.7(6) . . ?
N4 C38 H38 117.7 . . ?
C39 C38 H38 117.7 . . ?
C40 C39 C38 117.6(6) . . ?
C40 C39 H39 121.2 . . ?
C38 C39 H39 121.2 . . ?
C39 C40 C41 120.3(6) . . ?
C39 C40 H40 119.8 . . ?
C41 C40 H40 119.8 . . ?
C37 C41 C40 117.8(5) . . ?
C37 C41 C42 120.1(6) . . ?
C40 C41 C42 122.1(6) . . ?
C43 C42 C41 119.2(6) . . ?
C43 C42 H42 120.4 . . ?
C41 C42 H42 120.4 . . ?
C42 C43 C44 123.0(6) . . ?
C42 C43 H43 118.5 . . ?
C44 C43 H43 118.5 . . ?
C45 C44 C48 118.2(6) . . ?
C45 C44 C43 123.3(5) . . ?
C48 C44 C43 118.5(5) . . ?
C46 C45 C44 119.1(5) . . ?
C46 C45 H45 120.4 . . ?
C44 C45 H45 120.4 . . ?
C45 C46 C47 119.9(6) . . ?
C45 C46 H46 120.0 . . ?
C47 C46 H46 120.0 . . ?
N5 C47 C46 123.0(6) . . ?
N5 C47 H47 118.5 . . ?
C46 C47 H47 118.5 . . ?
N5 C48 C44 122.3(5) . . ?
N5 C48 C37 118.8(5) . . ?
C44 C48 C37 118.9(5) . . ?
C34 C49 C27 102.8(4) . . ?
C34 C49 H49A 111.2 . . ?
C27 C49 H49A 111.2 . . ?
C34 C49 H49B 111.2 . . ?
C27 C49 H49B 111.2 . . ?
H49A C49 H49B 109.1 . . ?
C22 C50 C15 102.6(4) . . ?
C22 C50 H50A 111.2 . . ?
C15 C50 H50A 111.2 . . ?
C22 C50 H50B 111.2 . . ?
C15 C50 H50B 111.2 . . ?
H50A C50 H50B 109.2 . . ?
C10 C51 C3 102.7(4) . . ?
C10 C51 H51A 111.2 . . ?
C3 C51 H51A 111.2 . . ?
C10 C51 H51B 111.2 . . ?
C3 C51 H51B 111.2 . . ?
H51A C51 H51B 109.1 . . ?
C38 N4 C37 116.7(5) . . ?
C38 N4 Nd1 121.7(4) . . ?
C37 N4 Nd1 121.4(4) . . ?
C47 N5 C48 117.5(5) . . ?
C47 N5 Nd1 121.6(4) . . ?
C48 N5 Nd1 120.6(3) . . ?
O1 Nd1 O10 138.26(12) . . ?
O1 Nd1 O5 82.27(14) . . ?
O10 Nd1 O5 75.42(13) . . ?
O1 Nd1 O2 71.23(12) . . ?
O10 Nd1 O2 149.12(12) . . ?
O5 Nd1 O2 127.08(14) . . ?
O1 Nd1 O9 142.82(14) . . ?
O10 Nd1 O9 71.47(12) . . ?
O5 Nd1 O9 133.99(13) . . ?
O2 Nd1 O9 77.82(13) . . ?
O1 Nd1 O6 122.67(15) . . ?
O10 Nd1 O6 82.49(12) . . ?
O5 Nd1 O6 70.86(12) . . ?
O2 Nd1 O6 86.01(12) . . ?
O9 Nd1 O6 73.90(14) . . ?
O1 Nd1 N4 79.80(15) . . ?
O10 Nd1 N4 97.45(14) . . ?
O5 Nd1 N4 143.03(12) . . ?
O2 Nd1 N4 76.36(14) . . ?
O9 Nd1 N4 73.21(13) . . ?
O6 Nd1 N4 145.22(13) . . ?
O1 Nd1 N5 70.43(14) . . ?
O10 Nd1 N5 71.82(12) . . ?
O5 Nd1 N5 81.90(14) . . ?
O2 Nd1 N5 126.76(13) . . ?
O9 Nd1 N5 115.75(15) . . ?
O6 Nd1 N5 146.50(13) . . ?
N4 Nd1 N5 61.68(14) . . ?
C2 O1 Nd1 131.4(4) . . ?
C4 O2 Nd1 128.7(3) . . ?
C7 O3 C11 117.1(5) . . ?
C8 O4 C12 117.8(5) . . ?
C14 O5 Nd1 128.5(3) . . ?
C16 O6 Nd1 124.7(3) . . ?
C19 O7 C23 117.0(4) . . ?
C20 O8 C24 117.6(5) . . ?
C26 O9 Nd1 130.4(4) . . ?
C28 O10 Nd1 127.5(3) . . ?
C31 O11 C35 115.9(5) . . ?
C32 O12 C36 118.0(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
F3 C1 C2 O1 45.0(13) . . . . ?
F2 C1 C2 O1 -168.6(9) . . . . ?
F1 C1 C2 O1 -59.5(9) . . . . ?
F3 C1 C2 C3 -130.1(10) . . . . ?
F2 C1 C2 C3 16.3(14) . . . . ?
F1 C1 C2 C3 125.4(8) . . . . ?
O1 C2 C3 C4 1.6(12) . . . . ?
C1 C2 C3 C4 176.1(7) . . . . ?
O1 C2 C3 C51 -179.8(7) . . . . ?
C1 C2 C3 C51 -5.3(12) . . . . ?
C2 C3 C4 O2 -1.0(11) . . . . ?
C51 C3 C4 O2 -179.9(6) . . . . ?
C2 C3 C4 C5 -178.8(6) . . . . ?
C51 C3 C4 C5 2.3(7) . . . . ?
O2 C4 C5 C10 -180.0(6) . . . . ?
C3 C4 C5 C10 -2.0(7) . . . . ?
O2 C4 C5 C6 -1.7(10) . . . . ?
C3 C4 C5 C6 176.2(6) . . . . ?
C10 C5 C6 C7 0.2(9) . . . . ?
C4 C5 C6 C7 -177.9(6) . . . . ?
C5 C6 C7 O3 178.1(6) . . . . ?
C5 C6 C7 C8 -2.0(10) . . . . ?
C6 C7 C8 O4 -177.5(6) . . . . ?
O3 C7 C8 O4 2.4(9) . . . . ?
C6 C7 C8 C9 3.2(10) . . . . ?
O3 C7 C8 C9 -176.8(6) . . . . ?
O4 C8 C9 C10 178.3(6) . . . . ?
C7 C8 C9 C10 -2.6(10) . . . . ?
C6 C5 C10 C9 0.4(10) . . . . ?
C4 C5 C10 C9 178.8(6) . . . . ?
C6 C5 C10 C51 -177.4(6) . . . . ?
C4 C5 C10 C51 1.0(7) . . . . ?
C8 C9 C10 C5 0.8(10) . . . . ?
C8 C9 C10 C51 178.2(7) . . . . ?
F5 C13 C14 O5 53.6(8) . . . . ?
F6 C13 C14 O5 -63.9(8) . . . . ?
F4 C13 C14 O5 176.4(6) . . . . ?
F5 C13 C14 C15 -127.9(7) . . . . ?
F6 C13 C14 C15 114.7(7) . . . . ?
F4 C13 C14 C15 -5.0(10) . . . . ?
O5 C14 C15 C16 -5.1(10) . . . . ?
C13 C14 C15 C16 176.6(6) . . . . ?
O5 C14 C15 C50 173.7(6) . . . . ?
C13 C14 C15 C50 -4.6(10) . . . . ?
C14 C15 C16 O6 -0.4(9) . . . . ?
C50 C15 C16 O6 -179.4(5) . . . . ?
C14 C15 C16 C17 -179.6(5) . . . . ?
C50 C15 C16 C17 1.4(6) . . . . ?
O6 C16 C17 C22 178.4(5) . . . . ?
C15 C16 C17 C22 -2.3(6) . . . . ?
O6 C16 C17 C18 1.2(9) . . . . ?
C15 C16 C17 C18 -179.5(6) . . . . ?
C22 C17 C18 C19 1.1(8) . . . . ?
C16 C17 C18 C19 178.0(6) . . . . ?
C17 C18 C19 O7 178.0(6) . . . . ?
C17 C18 C19 C20 -0.6(9) . . . . ?
O7 C19 C20 O8 1.2(8) . . . . ?
C18 C19 C20 O8 180.0(6) . . . . ?
O7 C19 C20 C21 -179.3(6) . . . . ?
C18 C19 C20 C21 -0.5(9) . . . . ?
O8 C20 C21 C22 -179.4(6) . . . . ?
C19 C20 C21 C22 1.1(9) . . . . ?
C18 C17 C22 C21 -0.6(9) . . . . ?
C16 C17 C22 C21 -178.0(5) . . . . ?
C18 C17 C22 C50 179.8(5) . . . . ?
C16 C17 C22 C50 2.3(7) . . . . ?
C20 C21 C22 C17 -0.6(9) . . . . ?
C20 C21 C22 C50 179.0(6) . . . . ?
F8 C25 C26 O9 128.4(7) . . . . ?
F7 C25 C26 O9 1.8(9) . . . . ?
F9 C25 C26 O9 -113.6(6) . . . . ?
F8 C25 C26 C27 -52.2(9) . . . . ?
F7 C25 C26 C27 -178.8(6) . . . . ?
F9 C25 C26 C27 65.8(8) . . . . ?
O9 C26 C27 C28 -8.3(10) . . . . ?
C25 C26 C27 C28 172.4(6) . . . . ?
O9 C26 C27 C49 173.0(6) . . . . ?
C25 C26 C27 C49 -6.3(10) . . . . ?
C26 C27 C28 O10 2.3(10) . . . . ?
C49 C27 C28 O10 -178.8(6) . . . . ?
C26 C27 C28 C29 -178.4(6) . . . . ?
C49 C27 C28 C29 0.5(7) . . . . ?
O10 C28 C29 C34 177.7(5) . . . . ?
C27 C28 C29 C34 -1.6(7) . . . . ?
O10 C28 C29 C30 0.0(10) . . . . ?
C27 C28 C29 C30 -179.3(6) . . . . ?
C34 C29 C30 C31 0.6(9) . . . . ?
C28 C29 C30 C31 178.1(6) . . . . ?
C29 C30 C31 O11 178.3(6) . . . . ?
C29 C30 C31 C32 -2.0(9) . . . . ?
O11 C31 C32 O12 1.1(8) . . . . ?
C30 C31 C32 O12 -178.6(6) . . . . ?
O11 C31 C32 C33 -178.5(6) . . . . ?
C30 C31 C32 C33 1.8(10) . . . . ?
O12 C32 C33 C34 -179.6(6) . . . . ?
C31 C32 C33 C34 -0.1(10) . . . . ?
C30 C29 C34 C33 1.1(9) . . . . ?
C28 C29 C34 C33 -176.8(5) . . . . ?
C30 C29 C34 C49 179.9(5) . . . . ?
C28 C29 C34 C49 2.1(7) . . . . ?
C32 C33 C34 C29 -1.3(9) . . . . ?
C32 C33 C34 C49 -179.9(6) . . . . ?
N4 C38 C39 C40 3.5(10) . . . . ?
C38 C39 C40 C41 0.2(10) . . . . ?
N4 C37 C41 C40 1.6(9) . . . . ?
C48 C37 C41 C40 -177.9(5) . . . . ?
N4 C37 C41 C42 -178.3(5) . . . . ?
C48 C37 C41 C42 2.2(9) . . . . ?
C39 C40 C41 C37 -2.6(10) . . . . ?
C39 C40 C41 C42 177.4(6) . . . . ?
C37 C41 C42 C43 -0.3(10) . . . . ?
C40 C41 C42 C43 179.7(6) . . . . ?
C41 C42 C43 C44 -2.0(10) . . . . ?
C42 C43 C44 C45 -176.8(6) . . . . ?
C42 C43 C44 C48 2.4(9) . . . . ?
C48 C44 C45 C46 -1.6(8) . . . . ?
C43 C44 C45 C46 177.6(6) . . . . ?
C44 C45 C46 C47 2.0(9) . . . . ?
C45 C46 C47 N5 -0.8(9) . . . . ?
C45 C44 C48 N5 0.1(8) . . . . ?
C43 C44 C48 N5 -179.2(5) . . . . ?
C45 C44 C48 C37 178.8(5) . . . . ?
C43 C44 C48 C37 -0.5(8) . . . . ?
N4 C37 C48 N5 -2.5(7) . . . . ?
C41 C37 C48 N5 177.0(5) . . . . ?
N4 C37 C48 C44 178.8(5) . . . . ?
C41 C37 C48 C44 -1.7(8) . . . . ?
C29 C34 C49 C27 -1.7(7) . . . . ?
C33 C34 C49 C27 177.0(6) . . . . ?
C26 C27 C49 C34 179.5(6) . . . . ?
C28 C27 C49 C34 0.7(7) . . . . ?
C17 C22 C50 C15 -1.4(6) . . . . ?
C21 C22 C50 C15 178.9(6) . . . . ?
C14 C15 C50 C22 -179.0(6) . . . . ?
C16 C15 C50 C22 -0.1(6) . . . . ?
C5 C10 C51 C3 0.4(7) . . . . ?
C9 C10 C51 C3 -177.2(6) . . . . ?
C2 C3 C51 C10 179.6(7) . . . . ?
C4 C3 C51 C10 -1.7(7) . . . . ?
C39 C38 N4 C37 -4.5(9) . . . . ?
C39 C38 N4 Nd1 170.0(5) . . . . ?
C41 C37 N4 C38 1.8(8) . . . . ?
C48 C37 N4 C38 -178.7(5) . . . . ?
C41 C37 N4 Nd1 -172.7(4) . . . . ?
C48 C37 N4 Nd1 6.8(6) . . . . ?
C46 C47 N5 C48 -0.7(8) . . . . ?
C46 C47 N5 Nd1 -175.4(4) . . . . ?
C44 C48 N5 C47 1.0(8) . . . . ?
C37 C48 N5 C47 -177.6(5) . . . . ?
C44 C48 N5 Nd1 175.8(4) . . . . ?
C37 C48 N5 Nd1 -2.9(6) . . . . ?
C38 N4 Nd1 O1 -106.7(4) . . . . ?
C37 N4 Nd1 O1 67.4(4) . . . . ?
C38 N4 Nd1 O10 115.4(4) . . . . ?
C37 N4 Nd1 O10 -70.4(4) . . . . ?
C38 N4 Nd1 O5 -168.9(4) . . . . ?
C37 N4 Nd1 O5 5.2(5) . . . . ?
C38 N4 Nd1 O2 -33.8(4) . . . . ?
C37 N4 Nd1 O2 140.4(4) . . . . ?
C38 N4 Nd1 O9 47.4(4) . . . . ?
C37 N4 Nd1 O9 -138.4(4) . . . . ?
C38 N4 Nd1 O6 27.9(5) . . . . ?
C37 N4 Nd1 O6 -158.0(3) . . . . ?
C38 N4 Nd1 N5 -179.9(5) . . . . ?
C37 N4 Nd1 N5 -5.7(4) . . . . ?
C47 N5 Nd1 O1 90.1(4) . . . . ?
C48 N5 Nd1 O1 -84.4(4) . . . . ?
C47 N5 Nd1 O10 -71.8(4) . . . . ?
C48 N5 Nd1 O10 113.7(4) . . . . ?
C47 N5 Nd1 O5 5.4(4) . . . . ?
C48 N5 Nd1 O5 -169.1(4) . . . . ?
C47 N5 Nd1 O2 136.3(4) . . . . ?
C48 N5 Nd1 O2 -38.2(4) . . . . ?
C47 N5 Nd1 O9 -129.8(4) . . . . ?
C48 N5 Nd1 O9 55.7(4) . . . . ?
C47 N5 Nd1 O6 -30.0(5) . . . . ?
C48 N5 Nd1 O6 155.5(3) . . . . ?
C47 N5 Nd1 N4 178.8(5) . . . . ?
C48 N5 Nd1 N4 4.3(4) . . . . ?
C3 C2 O1 Nd1 27.0(11) . . . . ?
C1 C2 O1 Nd1 -147.7(6) . . . . ?
O10 Nd1 O1 C2 133.9(5) . . . . ?
O5 Nd1 O1 C2 -168.3(6) . . . . ?
O2 Nd1 O1 C2 -34.8(5) . . . . ?
O9 Nd1 O1 C2 0.4(7) . . . . ?
O6 Nd1 O1 C2 -107.0(6) . . . . ?
N4 Nd1 O1 C2 44.1(6) . . . . ?
N5 Nd1 O1 C2 107.6(6) . . . . ?
C3 C4 O2 Nd1 -26.7(9) . . . . ?
C5 C4 O2 Nd1 150.8(4) . . . . ?
O1 Nd1 O2 C4 33.7(5) . . . . ?
O10 Nd1 O2 C4 -131.6(5) . . . . ?
O5 Nd1 O2 C4 97.9(5) . . . . ?
O9 Nd1 O2 C4 -125.4(5) . . . . ?
O6 Nd1 O2 C4 160.3(5) . . . . ?
N4 Nd1 O2 C4 -50.0(5) . . . . ?
N5 Nd1 O2 C4 -12.2(6) . . . . ?
C6 C7 O3 C11 -4.2(10) . . . . ?
C8 C7 O3 C11 175.8(6) . . . . ?
C9 C8 O4 C12 -1.2(10) . . . . ?
C7 C8 O4 C12 179.6(7) . . . . ?
C15 C14 O5 Nd1 -27.7(8) . . . . ?
C13 C14 O5 Nd1 150.8(4) . . . . ?
O1 Nd1 O5 C14 168.6(5) . . . . ?
O10 Nd1 O5 C14 -47.0(4) . . . . ?
O2 Nd1 O5 C14 109.3(4) . . . . ?
O9 Nd1 O5 C14 -2.0(5) . . . . ?
O6 Nd1 O5 C14 40.0(4) . . . . ?
N4 Nd1 O5 C14 -129.9(4) . . . . ?
N5 Nd1 O5 C14 -120.2(5) . . . . ?
C15 C16 O6 Nd1 35.9(8) . . . . ?
C17 C16 O6 Nd1 -145.0(4) . . . . ?
O1 Nd1 O6 C16 -109.6(4) . . . . ?
O10 Nd1 O6 C16 34.4(4) . . . . ?
O5 Nd1 O6 C16 -42.7(4) . . . . ?
O2 Nd1 O6 C16 -174.3(4) . . . . ?
O9 Nd1 O6 C16 107.2(4) . . . . ?
N4 Nd1 O6 C16 126.7(4) . . . . ?
N5 Nd1 O6 C16 -5.3(6) . . . . ?
C18 C19 O7 C23 -13.8(9) . . . . ?
C20 C19 O7 C23 164.9(6) . . . . ?
C21 C20 O8 C24 1.8(10) . . . . ?
C19 C20 O8 C24 -178.7(7) . . . . ?
C27 C26 O9 Nd1 -19.8(10) . . . . ?
C25 C26 O9 Nd1 159.5(4) . . . . ?
O1 Nd1 O9 C26 -177.9(4) . . . . ?
O10 Nd1 O9 C26 32.7(5) . . . . ?
O5 Nd1 O9 C26 -13.5(6) . . . . ?
O2 Nd1 O9 C26 -143.9(5) . . . . ?
O6 Nd1 O9 C26 -54.6(5) . . . . ?
N4 Nd1 O9 C26 136.8(5) . . . . ?
N5 Nd1 O9 C26 90.9(5) . . . . ?
C27 C28 O10 Nd1 30.6(9) . . . . ?
C29 C28 O10 Nd1 -148.5(4) . . . . ?
O1 Nd1 O10 C28 170.9(4) . . . . ?
O5 Nd1 O10 C28 110.9(5) . . . . ?
O2 Nd1 O10 C28 -30.2(6) . . . . ?
O9 Nd1 O10 C28 -36.6(5) . . . . ?
O6 Nd1 O10 C28 38.8(5) . . . . ?
N4 Nd1 O10 C28 -106.1(5) . . . . ?
N5 Nd1 O10 C28 -162.9(5) . . . . ?
C30 C31 O11 C35 -3.3(10) . . . . ?
C32 C31 O11 C35 177.0(6) . . . . ?
C33 C32 O12 C36 -5.7(10) . . . . ?
C31 C32 O12 C36 174.7(6) . . . . ?
_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full 27.56
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max 1.195
_refine_diff_density_min -0.868
_refine_diff_density_rms 0.089
_database_code_depnum_ccdc_archive 'CCDC 931140'
#######################################################################
#
# 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_exp_683
#TrackingRef '5-ccdc-921510.CIF'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C13 H11 F3 O4'
_chemical_formula_sum 'C13 H11 F3 O4'
_chemical_formula_weight 288.22
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'
_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 8.4438(6)
_cell_length_b 11.4961(8)
_cell_length_c 13.5973(9)
_cell_angle_alpha 103.513(6)
_cell_angle_beta 96.609(6)
_cell_angle_gamma 95.597(6)
_cell_volume 1264.21(15)
_cell_formula_units_Z 4
_cell_measurement_temperature 293(2)
_cell_measurement_reflns_used 2087
_cell_measurement_theta_min 3.0772
_cell_measurement_theta_max 29.5825
_exptl_crystal_description block
_exptl_crystal_colour green
_exptl_crystal_size_max 0.22
_exptl_crystal_size_mid 0.21
_exptl_crystal_size_min 0.19
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.514
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 592
_exptl_absorpt_coefficient_mu 0.139
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9700
_exptl_absorpt_correction_T_max 0.9740
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 293(2)
_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 'Xcalibur, Eos'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean 16.1954
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 8241
_diffrn_reflns_av_R_equivalents 0.0169
_diffrn_reflns_av_unetI/netI 0.0303
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_k_min -13
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_l_min -16
_diffrn_reflns_limit_l_max 14
_diffrn_reflns_theta_min 3.08
_diffrn_reflns_theta_max 25.00
_reflns_number_total 4434
_reflns_number_gt 3119
_reflns_threshold_expression >2sigma(I)
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)'
_computing_publication_material SHELXL-97
_refine_special_details
;
dfix 1.33 0.01 c1 f1 c1 f2 c1 f3
dfix 1.33 0.01 c1 f1' c1 f2' c1 f3'
dfix 1.33 0.01 c14 f4 c14 f5 c14 f6
dfix 1.33 0.01 c14 f4' c14 f5' c14 f6'
isor 0.01 f1 f3 f1' f3' f2 f2' f4 f4' f5 f5' f6 f6'
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0487P)^2^+0.2189P] where P=(Fo^2^+2Fc^2^)/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 4434
_refine_ls_number_parameters 423
_refine_ls_number_restraints 84
_refine_ls_R_factor_all 0.0702
_refine_ls_R_factor_gt 0.0458
_refine_ls_wR_factor_ref 0.1194
_refine_ls_wR_factor_gt 0.1033
_refine_ls_goodness_of_fit_ref 1.022
_refine_ls_restrained_S_all 1.148
_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
F5' F 0.6434(19) 0.8462(10) 0.4115(9) 0.107(3) Uani 0.45(2) 1 d PDU A 2
F6' F 0.4253(11) 0.8001(18) 0.4564(10) 0.124(4) Uani 0.45(2) 1 d PDU A 2
F4' F 0.610(2) 0.6898(10) 0.4659(12) 0.117(4) Uani 0.45(2) 1 d PDU A 2
F1' F 1.0396(19) 0.6758(6) 0.1720(8) 0.140(4) Uani 0.437(12) 1 d PDU B 2
F3' F 0.8871(7) 0.7865(10) 0.2418(8) 0.103(3) Uani 0.437(12) 1 d PDU B 2
F2' F 1.1127(15) 0.7990(11) 0.3156(10) 0.146(4) Uani 0.437(12) 1 d PDU B 2
F1 F 0.9293(11) 0.6999(7) 0.1584(5) 0.123(3) Uani 0.563(12) 1 d PDU B 1
F2 F 1.1416(5) 0.7454(7) 0.2611(7) 0.097(2) Uani 0.563(12) 1 d PDU B 1
F3 F 0.9399(14) 0.8263(6) 0.2997(10) 0.150(3) Uani 0.563(12) 1 d PDU B 1
F4 F 0.5453(17) 0.7003(7) 0.4847(5) 0.095(2) Uani 0.55(2) 1 d PDU A 1
F5 F 0.6925(10) 0.8010(14) 0.4108(8) 0.121(3) Uani 0.55(2) 1 d PDU A 1
F6 F 0.4635(15) 0.8458(8) 0.4401(6) 0.103(3) Uani 0.55(2) 1 d PDU A 1
C1 C 0.9899(3) 0.7230(3) 0.2584(2) 0.0729(8) Uani 1 1 d D . .
C2 C 0.9370(3) 0.6261(2) 0.3081(2) 0.0603(6) Uani 1 1 d . B .
C3 C 0.8349(3) 0.5266(2) 0.26098(18) 0.0549(6) Uani 1 1 d . . .
C4 C 0.7836(3) 0.4417(2) 0.31959(18) 0.0539(6) Uani 1 1 d . B .
C5 C 0.6698(3) 0.3466(2) 0.25090(16) 0.0492(5) Uani 1 1 d . . .
C6 C 0.6540(3) 0.3672(2) 0.15427(17) 0.0504(5) Uani 1 1 d . B .
C7 C 0.7547(3) 0.4816(2) 0.15178(18) 0.0594(6) Uani 1 1 d . B .
H7A H 0.6885 0.5391 0.1320 0.071 Uiso 1 1 calc R . .
H7B H 0.8333 0.4656 0.1052 0.071 Uiso 1 1 calc R . .
C8 C 0.5838(3) 0.2469(2) 0.27172(17) 0.0525(6) Uani 1 1 d . B .
H8 H 0.5951 0.2342 0.3371 0.063 Uiso 1 1 calc R . .
C9 C 0.4825(3) 0.1685(2) 0.19317(17) 0.0518(6) Uani 1 1 d . . .
C10 C 0.4683(3) 0.1877(2) 0.09282(16) 0.0515(6) Uani 1 1 d . B .
C11 C 0.5531(3) 0.2868(2) 0.07412(17) 0.0548(6) Uani 1 1 d . . .
H11 H 0.5430 0.2998 0.0088 0.066 Uiso 1 1 calc R B .
C12 C 0.3987(4) 0.0412(2) 0.29734(19) 0.0796(8) Uani 1 1 d . . .
H12A H 0.5071 0.0292 0.3186 0.119 Uiso 1 1 calc R B .
H12B H 0.3276 -0.0309 0.2926 0.119 Uiso 1 1 calc R . .
H12C H 0.3685 0.1069 0.3464 0.119 Uiso 1 1 calc R . .
C13 C 0.3535(3) 0.1109(3) -0.08154(18) 0.0737(8) Uani 1 1 d . B .
H13A H 0.3134 0.1849 -0.0866 0.111 Uiso 1 1 calc R . .
H13B H 0.2807 0.0439 -0.1239 0.111 Uiso 1 1 calc R . .
H13C H 0.4573 0.1096 -0.1038 0.111 Uiso 1 1 calc R . .
C14 C 0.5419(3) 0.7540(2) 0.4098(2) 0.0659(7) Uani 1 1 d D . .
C15 C 0.4721(3) 0.6756(2) 0.30726(18) 0.0569(6) Uani 1 1 d . A .
C16 C 0.3869(3) 0.5664(2) 0.29218(16) 0.0511(6) Uani 1 1 d . . .
C17 C 0.3389(3) 0.4949(2) 0.36582(16) 0.0537(6) Uani 1 1 d . A .
H17A H 0.2869 0.5423 0.4186 0.064 Uiso 1 1 calc R . .
H17B H 0.4311 0.4662 0.3976 0.064 Uiso 1 1 calc R . .
C18 C 0.2234(3) 0.3918(2) 0.29784(16) 0.0494(5) Uani 1 1 d . . .
C19 C 0.2093(3) 0.3975(2) 0.19659(16) 0.0503(5) Uani 1 1 d . A .
C20 C 0.3092(3) 0.5038(2) 0.18915(17) 0.0544(6) Uani 1 1 d . A .
C21 C 0.1352(3) 0.2992(2) 0.32522(17) 0.0540(6) Uani 1 1 d . A .
H21 H 0.1440 0.2946 0.3930 0.065 Uiso 1 1 calc R . .
C22 C 0.0341(3) 0.2140(2) 0.24999(18) 0.0563(6) Uani 1 1 d . . .
C23 C 0.0201(3) 0.2197(2) 0.14621(17) 0.0564(6) Uani 1 1 d . A .
C24 C 0.1077(3) 0.3107(2) 0.11948(17) 0.0567(6) Uani 1 1 d . . .
H24 H 0.1003 0.3150 0.0517 0.068 Uiso 1 1 calc R A .
C25 C -0.1054(3) 0.1316(3) -0.02418(19) 0.0826(9) Uani 1 1 d . A .
H25A H -0.1419 0.2061 -0.0313 0.124 Uiso 1 1 calc R . .
H25B H -0.1836 0.0653 -0.0620 0.124 Uiso 1 1 calc R . .
H25C H -0.0048 0.1243 -0.0501 0.124 Uiso 1 1 calc R . .
C26 C -0.0619(4) 0.1131(3) 0.3701(2) 0.0855(9) Uani 1 1 d . . .
H26A H 0.0434 0.1039 0.3998 0.128 Uiso 1 1 calc R A .
H26B H -0.1366 0.0453 0.3717 0.128 Uiso 1 1 calc R . .
H26C H -0.0948 0.1859 0.4082 0.128 Uiso 1 1 calc R . .
O1 O 0.8304(2) 0.45312(15) 0.41236(12) 0.0682(5) Uani 1 1 d . . .
O2 O 1.0010(2) 0.65183(17) 0.40634(14) 0.0771(5) Uani 1 1 d . . .
H2 H 0.9648 0.5997 0.4328 0.116 Uiso 1 1 calc R B .
O3 O 0.3885(2) 0.06839(14) 0.20066(12) 0.0645(5) Uani 1 1 d . B .
O4 O 0.36711(19) 0.10251(15) 0.02231(12) 0.0637(5) Uani 1 1 d . . .
O5 O 0.4975(2) 0.72855(16) 0.23226(13) 0.0765(5) Uani 1 1 d . . .
H5 H 0.4557 0.6836 0.1773 0.115 Uiso 1 1 calc R A .
O6 O 0.3266(2) 0.54092(16) 0.11084(12) 0.0725(5) Uani 1 1 d . . .
O7 O -0.0846(2) 0.13010(16) 0.08095(13) 0.0731(5) Uani 1 1 d . . .
O8 O -0.0587(2) 0.11929(16) 0.26688(13) 0.0725(5) Uani 1 1 d . A .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F5' 0.138(7) 0.076(4) 0.091(4) 0.017(3) 0.009(5) -0.045(4)
F6' 0.098(4) 0.153(8) 0.086(5) -0.035(5) 0.016(3) 0.002(5)
F4' 0.131(7) 0.102(4) 0.098(6) 0.024(4) -0.060(5) 0.018(5)
F1' 0.192(9) 0.124(5) 0.143(7) 0.069(5) 0.100(7) 0.026(5)
F3' 0.077(3) 0.117(6) 0.147(7) 0.094(5) 0.006(3) 0.034(3)
F2' 0.135(7) 0.132(7) 0.163(7) 0.085(5) -0.049(5) -0.064(5)
F1 0.140(5) 0.118(5) 0.107(4) 0.070(3) -0.027(3) -0.051(4)
F2 0.047(2) 0.107(4) 0.155(5) 0.072(4) 0.017(3) 0.003(2)
F3 0.200(8) 0.071(3) 0.212(7) 0.053(4) 0.103(6) 0.047(4)
F4 0.150(6) 0.069(3) 0.056(2) 0.024(2) -0.016(3) -0.016(3)
F5 0.080(3) 0.145(6) 0.105(4) -0.015(5) 0.011(2) -0.031(4)
F6 0.138(6) 0.078(4) 0.081(3) -0.002(2) -0.012(3) 0.041(4)
C1 0.0648(18) 0.0653(19) 0.090(2) 0.0294(17) 0.0045(17) -0.0001(15)
C2 0.0567(14) 0.0625(16) 0.0665(17) 0.0236(13) 0.0098(12) 0.0117(13)
C3 0.0541(13) 0.0548(14) 0.0591(15) 0.0195(12) 0.0109(11) 0.0063(12)
C4 0.0606(14) 0.0569(14) 0.0469(14) 0.0145(11) 0.0121(11) 0.0116(11)
C5 0.0560(13) 0.0494(13) 0.0453(13) 0.0146(11) 0.0107(10) 0.0102(11)
C6 0.0559(13) 0.0541(14) 0.0470(13) 0.0198(11) 0.0116(10) 0.0127(11)
C7 0.0637(14) 0.0649(16) 0.0567(15) 0.0291(13) 0.0093(11) 0.0076(12)
C8 0.0674(15) 0.0525(14) 0.0414(13) 0.0165(11) 0.0114(11) 0.0100(12)
C9 0.0619(14) 0.0470(13) 0.0496(14) 0.0145(11) 0.0146(11) 0.0089(11)
C10 0.0567(13) 0.0536(14) 0.0445(13) 0.0111(11) 0.0086(10) 0.0087(11)
C11 0.0604(14) 0.0647(15) 0.0431(13) 0.0194(12) 0.0081(11) 0.0107(12)
C12 0.116(2) 0.0647(17) 0.0603(17) 0.0291(14) 0.0109(15) -0.0117(16)
C13 0.0858(18) 0.087(2) 0.0432(14) 0.0135(13) 0.0042(13) 0.0003(15)
C14 0.0721(18) 0.0642(18) 0.0604(17) 0.0202(14) 0.0035(14) -0.0008(15)
C15 0.0629(14) 0.0627(16) 0.0503(14) 0.0234(12) 0.0080(11) 0.0107(12)
C16 0.0572(13) 0.0542(14) 0.0438(13) 0.0148(11) 0.0079(10) 0.0099(11)
C17 0.0603(14) 0.0583(14) 0.0444(13) 0.0176(11) 0.0058(10) 0.0073(11)
C18 0.0515(13) 0.0549(14) 0.0436(13) 0.0139(11) 0.0073(10) 0.0116(11)
C19 0.0537(13) 0.0559(14) 0.0431(13) 0.0133(11) 0.0092(10) 0.0113(11)
C20 0.0612(14) 0.0601(15) 0.0451(14) 0.0161(12) 0.0102(11) 0.0121(12)
C21 0.0588(14) 0.0602(15) 0.0451(13) 0.0179(11) 0.0061(11) 0.0079(12)
C22 0.0564(14) 0.0583(15) 0.0558(15) 0.0168(12) 0.0097(11) 0.0073(12)
C23 0.0551(14) 0.0608(15) 0.0491(14) 0.0073(12) 0.0041(11) 0.0056(12)
C24 0.0613(14) 0.0660(16) 0.0430(13) 0.0128(12) 0.0079(11) 0.0105(12)
C25 0.090(2) 0.094(2) 0.0509(16) 0.0073(15) 0.0015(14) -0.0137(16)
C26 0.096(2) 0.089(2) 0.0737(19) 0.0339(16) 0.0140(16) -0.0137(17)
O1 0.0841(12) 0.0703(11) 0.0467(10) 0.0151(8) 0.0048(8) -0.0034(9)
O2 0.0868(13) 0.0682(12) 0.0700(13) 0.0167(10) 0.0006(10) -0.0065(10)
O3 0.0854(12) 0.0548(10) 0.0516(10) 0.0162(8) 0.0092(8) -0.0056(9)
O4 0.0755(11) 0.0667(11) 0.0442(9) 0.0111(8) 0.0036(8) -0.0021(9)
O5 0.0955(14) 0.0771(13) 0.0607(11) 0.0311(10) 0.0111(10) -0.0049(10)
O6 0.0949(13) 0.0809(12) 0.0452(10) 0.0258(9) 0.0112(9) 0.0021(10)
O7 0.0805(12) 0.0758(12) 0.0533(11) 0.0087(9) 0.0017(9) -0.0110(10)
O8 0.0810(12) 0.0707(12) 0.0632(11) 0.0202(9) 0.0090(9) -0.0101(10)
_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
F5' C14 1.291(7) . ?
F6' C14 1.319(8) . ?
F4' C14 1.305(8) . ?
F1' C1 1.308(6) . ?
F3' C1 1.222(6) . ?
F2' C1 1.328(6) . ?
F1 C1 1.351(5) . ?
F2 C1 1.277(5) . ?
F3 C1 1.320(6) . ?
F4 C14 1.307(6) . ?
F5 C14 1.329(6) . ?
F6 C14 1.311(6) . ?
C1 C2 1.490(4) . ?
C2 O2 1.335(3) . ?
C2 C3 1.342(3) . ?
C3 C4 1.461(3) . ?
C3 C7 1.507(3) . ?
C4 O1 1.250(3) . ?
C4 C5 1.451(3) . ?
C5 C6 1.383(3) . ?
C5 C8 1.399(3) . ?
C6 C11 1.389(3) . ?
C6 C7 1.505(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.369(3) . ?
C8 H8 0.9300 . ?
C9 O3 1.364(3) . ?
C9 C10 1.426(3) . ?
C10 O4 1.349(3) . ?
C10 C11 1.376(3) . ?
C11 H11 0.9300 . ?
C12 O3 1.416(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 O4 1.430(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.491(3) . ?
C15 O5 1.331(3) . ?
C15 C16 1.344(3) . ?
C16 C20 1.461(3) . ?
C16 C17 1.502(3) . ?
C17 C18 1.505(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.386(3) . ?
C18 C21 1.386(3) . ?
C19 C24 1.403(3) . ?
C19 C20 1.446(3) . ?
C20 O6 1.254(3) . ?
C21 C22 1.379(3) . ?
C21 H21 0.9300 . ?
C22 O8 1.358(3) . ?
C22 C23 1.420(3) . ?
C23 O7 1.358(3) . ?
C23 C24 1.365(3) . ?
C24 H24 0.9300 . ?
C25 O7 1.424(3) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 O8 1.425(3) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
O2 H2 0.8200 . ?
O5 H5 0.8200 . ?
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
F3' C1 F2 127.9(4) . . ?
F3' C1 F1' 108.4(6) . . ?
F2 C1 F1' 66.8(5) . . ?
F3' C1 F3 39.3(4) . . ?
F2 C1 F3 106.4(5) . . ?
F1' C1 F3 135.8(5) . . ?
F3' C1 F2' 105.0(6) . . ?
F2 C1 F2' 41.3(6) . . ?
F1' C1 F2' 106.4(6) . . ?
F3 C1 F2' 70.3(6) . . ?
F3' C1 F1 67.2(4) . . ?
F2 C1 F1 104.8(4) . . ?
F1' C1 F1 44.4(4) . . ?
F3 C1 F1 104.1(5) . . ?
F2' C1 F1 132.6(5) . . ?
F3' C1 C2 114.6(4) . . ?
F2 C1 C2 115.3(3) . . ?
F1' C1 C2 110.0(4) . . ?
F3 C1 C2 111.7(4) . . ?
F2' C1 C2 111.9(4) . . ?
F1 C1 C2 113.5(3) . . ?
O2 C2 C3 124.0(2) . . ?
O2 C2 C1 111.6(2) . . ?
C3 C2 C1 124.5(2) . . ?
C2 C3 C4 119.4(2) . . ?
C2 C3 C7 131.3(2) . . ?
C4 C3 C7 109.3(2) . . ?
O1 C4 C5 127.9(2) . . ?
O1 C4 C3 124.7(2) . . ?
C5 C4 C3 107.4(2) . . ?
C6 C5 C8 121.8(2) . . ?
C6 C5 C4 109.21(19) . . ?
C8 C5 C4 129.0(2) . . ?
C5 C6 C11 120.1(2) . . ?
C5 C6 C7 111.9(2) . . ?
C11 C6 C7 128.0(2) . . ?
C6 C7 C3 102.22(18) . . ?
C6 C7 H7A 111.3 . . ?
C3 C7 H7A 111.3 . . ?
C6 C7 H7B 111.3 . . ?
C3 C7 H7B 111.3 . . ?
H7A C7 H7B 109.2 . . ?
C9 C8 C5 118.2(2) . . ?
C9 C8 H8 120.9 . . ?
C5 C8 H8 120.9 . . ?
O3 C9 C8 125.6(2) . . ?
O3 C9 C10 113.97(19) . . ?
C8 C9 C10 120.4(2) . . ?
O4 C10 C11 125.2(2) . . ?
O4 C10 C9 114.28(19) . . ?
C11 C10 C9 120.5(2) . . ?
C10 C11 C6 119.0(2) . . ?
C10 C11 H11 120.5 . . ?
C6 C11 H11 120.5 . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O4 C13 H13A 109.5 . . ?
O4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
F5' C14 F4' 108.3(7) . . ?
F5' C14 F4 122.5(6) . . ?
F4' C14 F4 28.4(7) . . ?
F5' C14 F6 76.5(5) . . ?
F4' C14 F6 127.4(8) . . ?
F4 C14 F6 103.8(5) . . ?
F5' C14 F6' 104.6(6) . . ?
F4' C14 F6' 107.5(7) . . ?
F4 C14 F6' 79.7(6) . . ?
F6 C14 F6' 30.1(6) . . ?
F5' C14 F5 30.7(5) . . ?
F4' C14 F5 83.4(6) . . ?
F4 C14 F5 106.2(6) . . ?
F6 C14 F5 105.9(5) . . ?
F6' C14 F5 130.7(6) . . ?
F5' C14 C15 116.7(5) . . ?
F4' C14 C15 110.0(6) . . ?
F4 C14 C15 115.1(4) . . ?
F6 C14 C15 113.5(4) . . ?
F6' C14 C15 109.2(5) . . ?
F5 C14 C15 111.6(5) . . ?
O5 C15 C16 123.6(2) . . ?
O5 C15 C14 112.2(2) . . ?
C16 C15 C14 124.1(2) . . ?
C15 C16 C20 119.1(2) . . ?
C15 C16 C17 131.6(2) . . ?
C20 C16 C17 109.0(2) . . ?
C16 C17 C18 102.48(18) . . ?
C16 C17 H17A 111.3 . . ?
C18 C17 H17A 111.3 . . ?
C16 C17 H17B 111.3 . . ?
C18 C17 H17B 111.3 . . ?
H17A C17 H17B 109.2 . . ?
C19 C18 C21 120.1(2) . . ?
C19 C18 C17 111.62(19) . . ?
C21 C18 C17 128.29(19) . . ?
C18 C19 C24 121.6(2) . . ?
C18 C19 C20 109.09(19) . . ?
C24 C19 C20 129.3(2) . . ?
O6 C20 C19 128.1(2) . . ?
O6 C20 C16 124.2(2) . . ?
C19 C20 C16 107.69(19) . . ?
C22 C21 C18 118.7(2) . . ?
C22 C21 H21 120.7 . . ?
C18 C21 H21 120.7 . . ?
O8 C22 C21 124.4(2) . . ?
O8 C22 C23 114.4(2) . . ?
C21 C22 C23 121.2(2) . . ?
O7 C23 C24 125.5(2) . . ?
O7 C23 C22 114.6(2) . . ?
C24 C23 C22 119.9(2) . . ?
C23 C24 C19 118.5(2) . . ?
C23 C24 H24 120.8 . . ?
C19 C24 H24 120.8 . . ?
O7 C25 H25A 109.5 . . ?
O7 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O7 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O8 C26 H26A 109.5 . . ?
O8 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O8 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C2 O2 H2 109.5 . . ?
C9 O3 C12 117.47(18) . . ?
C10 O4 C13 117.86(18) . . ?
C15 O5 H5 109.5 . . ?
C23 O7 C25 117.3(2) . . ?
C22 O8 C26 117.76(19) . . ?
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
F3' C1 C2 O2 -106.2(7) . . . . ?
F2 C1 C2 O2 58.3(6) . . . . ?
F1' C1 C2 O2 131.3(8) . . . . ?
F3 C1 C2 O2 -63.4(8) . . . . ?
F2' C1 C2 O2 13.2(10) . . . . ?
F1 C1 C2 O2 179.2(6) . . . . ?
F3' C1 C2 C3 72.4(7) . . . . ?
F2 C1 C2 C3 -123.1(6) . . . . ?
F1' C1 C2 C3 -50.1(9) . . . . ?
F3 C1 C2 C3 115.2(8) . . . . ?
F2' C1 C2 C3 -168.2(10) . . . . ?
F1 C1 C2 C3 -2.2(7) . . . . ?
O2 C2 C3 C4 2.4(4) . . . . ?
C1 C2 C3 C4 -176.0(2) . . . . ?
O2 C2 C3 C7 -178.4(2) . . . . ?
C1 C2 C3 C7 3.2(4) . . . . ?
C2 C3 C4 O1 -1.4(4) . . . . ?
C7 C3 C4 O1 179.2(2) . . . . ?
C2 C3 C4 C5 177.7(2) . . . . ?
C7 C3 C4 C5 -1.7(2) . . . . ?
O1 C4 C5 C6 -179.0(2) . . . . ?
C3 C4 C5 C6 2.0(2) . . . . ?
O1 C4 C5 C8 1.2(4) . . . . ?
C3 C4 C5 C8 -177.9(2) . . . . ?
C8 C5 C6 C11 -1.2(3) . . . . ?
C4 C5 C6 C11 178.89(19) . . . . ?
C8 C5 C6 C7 178.3(2) . . . . ?
C4 C5 C6 C7 -1.5(3) . . . . ?
C5 C6 C7 C3 0.5(2) . . . . ?
C11 C6 C7 C3 180.0(2) . . . . ?
C2 C3 C7 C6 -178.5(2) . . . . ?
C4 C3 C7 C6 0.8(2) . . . . ?
C6 C5 C8 C9 0.3(3) . . . . ?
C4 C5 C8 C9 -179.9(2) . . . . ?
C5 C8 C9 O3 -179.0(2) . . . . ?
C5 C8 C9 C10 1.1(3) . . . . ?
O3 C9 C10 O4 -1.3(3) . . . . ?
C8 C9 C10 O4 178.68(19) . . . . ?
O3 C9 C10 C11 178.4(2) . . . . ?
C8 C9 C10 C11 -1.6(3) . . . . ?
O4 C10 C11 C6 -179.7(2) . . . . ?
C9 C10 C11 C6 0.7(3) . . . . ?
C5 C6 C11 C10 0.7(3) . . . . ?
C7 C6 C11 C10 -178.8(2) . . . . ?
F5' C14 C15 O5 -14.6(10) . . . . ?
F4' C14 C15 O5 -138.6(10) . . . . ?
F4 C14 C15 O5 -168.9(8) . . . . ?
F6 C14 C15 O5 71.6(7) . . . . ?
F6' C14 C15 O5 103.7(11) . . . . ?
F5 C14 C15 O5 -47.9(9) . . . . ?
F5' C14 C15 C16 168.3(10) . . . . ?
F4' C14 C15 C16 44.4(10) . . . . ?
F4 C14 C15 C16 14.0(8) . . . . ?
F6 C14 C15 C16 -105.4(7) . . . . ?
F6' C14 C15 C16 -73.3(11) . . . . ?
F5 C14 C15 C16 135.1(9) . . . . ?
O5 C15 C16 C20 -3.6(4) . . . . ?
C14 C15 C16 C20 173.2(2) . . . . ?
O5 C15 C16 C17 -176.7(2) . . . . ?
C14 C15 C16 C17 0.0(4) . . . . ?
C15 C16 C17 C18 171.1(2) . . . . ?
C20 C16 C17 C18 -2.6(2) . . . . ?
C16 C17 C18 C19 2.4(2) . . . . ?
C16 C17 C18 C21 -177.0(2) . . . . ?
C21 C18 C19 C24 -0.4(3) . . . . ?
C17 C18 C19 C24 -179.8(2) . . . . ?
C21 C18 C19 C20 178.2(2) . . . . ?
C17 C18 C19 C20 -1.2(2) . . . . ?
C18 C19 C20 O6 -178.8(2) . . . . ?
C24 C19 C20 O6 -0.3(4) . . . . ?
C18 C19 C20 C16 -0.5(2) . . . . ?
C24 C19 C20 C16 177.9(2) . . . . ?
C15 C16 C20 O6 5.8(3) . . . . ?
C17 C16 C20 O6 -179.6(2) . . . . ?
C15 C16 C20 C19 -172.5(2) . . . . ?
C17 C16 C20 C19 2.1(2) . . . . ?
C19 C18 C21 C22 -0.1(3) . . . . ?
C17 C18 C21 C22 179.3(2) . . . . ?
C18 C21 C22 O8 -179.9(2) . . . . ?
C18 C21 C22 C23 0.3(3) . . . . ?
O8 C22 C23 O7 0.5(3) . . . . ?
C21 C22 C23 O7 -179.7(2) . . . . ?
O8 C22 C23 C24 -179.8(2) . . . . ?
C21 C22 C23 C24 0.1(3) . . . . ?
O7 C23 C24 C19 179.2(2) . . . . ?
C22 C23 C24 C19 -0.5(3) . . . . ?
C18 C19 C24 C23 0.7(3) . . . . ?
C20 C19 C24 C23 -177.6(2) . . . . ?
C8 C9 O3 C12 -1.5(3) . . . . ?
C10 C9 O3 C12 178.4(2) . . . . ?
C11 C10 O4 C13 4.1(3) . . . . ?
C9 C10 O4 C13 -176.2(2) . . . . ?
C24 C23 O7 C25 -0.4(3) . . . . ?
C22 C23 O7 C25 179.3(2) . . . . ?
C21 C22 O8 C26 5.4(3) . . . . ?
C23 C22 O8 C26 -174.7(2) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H5 O6 0.82 1.85 2.577(3) 146.8 .
O2 H2 O1 0.82 1.88 2.602(2) 146.1 .
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max 0.191
_refine_diff_density_min -0.165
_refine_diff_density_rms 0.035
_database_code_depnum_ccdc_archive 'CCDC 921510'