# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_author_name                'Zhang-Jun Hu'
_publ_contact_author_name        'Dr Zhang-Jun Hu'
_publ_contact_author_email       huzjun@tongji.edu.cn

data_eu
_database_code_depnum_ccdc_archive 'CCDC 838898'
#TrackingRef '- CCDC 838898_R.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C78 H71 Eu F9 N5 O6'
_chemical_formula_sum            'C78 H71 Eu F9 N5 O6'
_chemical_formula_weight         1497.36

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'
Eu Eu -0.1578 3.6682 '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

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.548(1)
_cell_length_b                   16.139(1)
_cell_length_c                   21.028(1)
_cell_angle_alpha                69.106(1)
_cell_angle_beta                 87.515(1)
_cell_angle_gamma                86.340(1)
_cell_volume                     3969.3(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    17818
_cell_measurement_theta_min      1.35
_cell_measurement_theta_max      27.50

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1532
_exptl_absorpt_coefficient_mu    0.861
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6726
_exptl_absorpt_correction_T_max  0.9188
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            28929
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0538
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.35
_diffrn_reflns_theta_max         25.05
_reflns_number_total             13957
_reflns_number_gt                10879
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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.
To refine the structure with reasonable C-F bond lengths, DFIX
command for C23-F4, C23-F5, C23-F6, C23'-F4', C23'-F5', C23'-F6' were
perfomed. To restrain atoms that are bond to others would move in similar
directions with sensible value, SIMU restraints can be found for C1-F1,
C1-F2, C1-F3, C1-C2, C23'-C24. Additionnally, although large solvent
accessible voids in the structure can be found in the cif, squeeze
command was not used here.
;

_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^)+(0.0795P)^2^+5.8668P] 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         13957
_refine_ls_number_parameters     929
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.1481
_refine_ls_wR_factor_gt          0.1339
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_restrained_S_all      0.972
_refine_ls_shift/su_max          0.002
_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 0.9163(18) 0.6937(8) 0.4783(5) 0.186(4) Uani 1 1 d U . .
C2 C 0.9036(11) 0.6666(5) 0.5544(4) 0.140(4) Uani 1 1 d U . .
C3 C 0.9071(8) 0.5795(5) 0.5912(4) 0.103(3) Uani 1 1 d . . .
H3 H 0.9154 0.5401 0.5679 0.124 Uiso 1 1 calc R . .
C4 C 0.8991(5) 0.5445(4) 0.6616(3) 0.0604(14) Uani 1 1 d . . .
C5 C 0.8993(5) 0.4474(4) 0.6995(3) 0.0597(14) Uani 1 1 d . . .
C6 C 0.9103(4) 0.4159(4) 0.7696(3) 0.0580(14) Uani 1 1 d . . .
H6 H 0.9185 0.4553 0.7920 0.070 Uiso 1 1 calc R . .
C7 C 0.9089(4) 0.3255(4) 0.8060(3) 0.0580(14) Uani 1 1 d . . .
C8 C 0.8963(5) 0.2667(4) 0.7707(3) 0.0639(15) Uani 1 1 d . . .
C9 C 0.8847(5) 0.2972(4) 0.7012(4) 0.0747(17) Uani 1 1 d . . .
H9 H 0.8754 0.2581 0.6785 0.090 Uiso 1 1 calc R . .
C10 C 0.8873(5) 0.3869(4) 0.6663(3) 0.0736(17) Uani 1 1 d . . .
H10 H 0.8809 0.4084 0.6193 0.088 Uiso 1 1 calc R . .
C11 C 0.9205(4) 0.2715(4) 0.8769(3) 0.0581(14) Uani 1 1 d . . .
C12 C 0.9377(5) 0.2888(4) 0.9353(3) 0.0670(16) Uani 1 1 d . . .
H12 H 0.9447 0.3467 0.9333 0.080 Uiso 1 1 calc R . .
C13 C 0.9445(5) 0.2188(5) 0.9966(3) 0.0801(19) Uani 1 1 d . . .
H13 H 0.9558 0.2297 1.0363 0.096 Uiso 1 1 calc R . .
C14 C 0.9347(6) 0.1324(5) 0.9995(4) 0.089(2) Uani 1 1 d . . .
H14 H 0.9395 0.0865 1.0415 0.107 Uiso 1 1 calc R . .
C15 C 0.9186(5) 0.1127(4) 0.9439(4) 0.082(2) Uani 1 1 d . . .
H15 H 0.9118 0.0545 0.9466 0.099 Uiso 1 1 calc R . .
C16 C 0.9124(4) 0.1835(4) 0.8819(3) 0.0648(16) Uani 1 1 d . . .
C17 C 0.8928(6) 0.1021(4) 0.8008(4) 0.088(2) Uani 1 1 d . . .
H17A H 0.8496 0.1146 0.7610 0.106 Uiso 1 1 calc R . .
H17B H 0.8601 0.0557 0.8384 0.106 Uiso 1 1 calc R . .
C18 C 1.0079(7) 0.0696(6) 0.7864(6) 0.126(3) Uani 1 1 d . . .
H18A H 1.0336 0.1099 0.7428 0.151 Uiso 1 1 calc R . .
H18B H 1.0549 0.0717 0.8211 0.151 Uiso 1 1 calc R . .
C19 C 1.0136(7) -0.0180(6) 0.7851(5) 0.114(3) Uani 1 1 d . . .
H19A H 0.9650 -0.0205 0.7513 0.137 Uiso 1 1 calc R . .
H19B H 0.9898 -0.0584 0.8291 0.137 Uiso 1 1 calc R . .
C20 C 1.1250(9) -0.0493(8) 0.7690(7) 0.148(4) Uani 1 1 d . . .
H20A H 1.1407 -0.0193 0.7210 0.177 Uiso 1 1 calc R . .
H20B H 1.1762 -0.0316 0.7943 0.177 Uiso 1 1 calc R . .
C21 C 1.1393(10) -0.1408(9) 0.7841(7) 0.182(6) Uani 1 1 d . . .
H21A H 1.0867 -0.1591 0.7600 0.218 Uiso 1 1 calc R . .
H21B H 1.1264 -0.1710 0.8325 0.218 Uiso 1 1 calc R . .
C22 C 1.2452(9) -0.1687(10) 0.7660(6) 0.186(6) Uani 1 1 d . . .
H22A H 1.2496 -0.2319 0.7776 0.279 Uiso 1 1 calc R . .
H22B H 1.2978 -0.1522 0.7906 0.279 Uiso 1 1 calc R . .
H22C H 1.2581 -0.1402 0.7180 0.279 Uiso 1 1 calc R . .
C23 C 0.9942(11) 0.5989(10) 0.9015(8) 0.074(4) Uani 0.69(3) 1 d PD A 1
C24 C 0.9342(4) 0.6738(3) 0.8464(2) 0.0486(12) Uani 1 1 d U . .
C25 C 0.8676(4) 0.7319(3) 0.8659(3) 0.0534(13) Uani 1 1 d . A .
H25 H 0.8544 0.7196 0.9121 0.064 Uiso 1 1 calc R . .
C26 C 0.8181(4) 0.8098(3) 0.8188(3) 0.0493(12) Uani 1 1 d . . .
C27 C 0.7576(4) 0.8741(3) 0.8443(3) 0.0515(12) Uani 1 1 d . A .
C28 C 0.7671(4) 0.8722(3) 0.9102(3) 0.0531(13) Uani 1 1 d . . .
H28 H 0.8101 0.8281 0.9407 0.064 Uiso 1 1 calc R A .
C29 C 0.7123(4) 0.9361(3) 0.9307(3) 0.0560(13) Uani 1 1 d . A .
C30 C 0.6457(5) 1.0020(4) 0.8840(3) 0.0650(15) Uani 1 1 d . . .
C31 C 0.6343(5) 1.0039(4) 0.8187(3) 0.0715(17) Uani 1 1 d . A .
H31 H 0.5905 1.0475 0.7884 0.086 Uiso 1 1 calc R . .
C32 C 0.6892(5) 0.9400(4) 0.7994(3) 0.0649(15) Uani 1 1 d . . .
H32 H 0.6811 0.9401 0.7556 0.078 Uiso 1 1 calc R A .
C33 C 0.7080(5) 0.9540(4) 0.9934(3) 0.0620(15) Uani 1 1 d . . .
C34 C 0.7539(5) 0.9139(4) 1.0561(3) 0.0710(16) Uani 1 1 d . A .
H34 H 0.8008 0.8643 1.0645 0.085 Uiso 1 1 calc R . .
C35 C 0.7290(6) 0.9487(5) 1.1058(4) 0.086(2) Uani 1 1 d . . .
H35 H 0.7582 0.9216 1.1486 0.103 Uiso 1 1 calc R A .
C36 C 0.6616(6) 1.0229(6) 1.0933(5) 0.097(2) Uani 1 1 d . A .
H36 H 0.6466 1.0452 1.1280 0.116 Uiso 1 1 calc R . .
C37 C 0.6156(6) 1.0653(5) 1.0311(5) 0.088(2) Uani 1 1 d . . .
H37 H 0.5707 1.1160 1.0229 0.106 Uiso 1 1 calc R A .
C38 C 0.6386(5) 1.0298(4) 0.9819(4) 0.0685(16) Uani 1 1 d . A .
C39 C 0.5388(5) 1.1397(4) 0.8833(4) 0.083(2) Uani 1 1 d . . .
H39A H 0.4933 1.1525 0.9174 0.100 Uiso 1 1 calc R A .
H39B H 0.4931 1.1310 0.8504 0.100 Uiso 1 1 calc R . .
C40 C 0.6066(5) 1.2184(5) 0.8475(4) 0.091(2) Uani 1 1 d . A .
H40A H 0.6490 1.2293 0.8809 0.109 Uiso 1 1 calc R . .
H40B H 0.6553 1.2040 0.8154 0.109 Uiso 1 1 calc R . .
C41 C 0.5402(6) 1.3022(5) 0.8098(5) 0.096(2) Uani 1 1 d . . .
H41A H 0.4881 1.2877 0.7832 0.116 Uiso 1 1 calc R A .
H41B H 0.5013 1.3221 0.8431 0.116 Uiso 1 1 calc R . .
C42 C 0.6019(7) 1.3768(5) 0.7637(5) 0.106(3) Uani 1 1 d . A .
H42A H 0.6460 1.3554 0.7332 0.127 Uiso 1 1 calc R . .
H42B H 0.6493 1.3951 0.7909 0.127 Uiso 1 1 calc R . .
C43 C 0.5343(7) 1.4571(5) 0.7215(5) 0.115(3) Uani 1 1 d . . .
H43A H 0.4835 1.4385 0.6965 0.138 Uiso 1 1 calc R A .
H43B H 0.4943 1.4817 0.7517 0.138 Uiso 1 1 calc R . .
C44 C 0.5992(9) 1.5279(7) 0.6723(6) 0.156(4) Uani 1 1 d . A .
H44A H 0.5526 1.5770 0.6469 0.234 Uiso 1 1 calc R . .
H44B H 0.6379 1.5043 0.6416 0.234 Uiso 1 1 calc R . .
H44C H 0.6486 1.5476 0.6968 0.234 Uiso 1 1 calc R . .
C45 C 0.5735(6) 0.9290(6) 0.6153(5) 0.105(3) Uani 1 1 d . . .
C46 C 0.6332(5) 0.8413(4) 0.6544(3) 0.0647(15) Uani 1 1 d . . .
C47 C 0.5792(5) 0.7823(4) 0.7083(3) 0.0693(17) Uani 1 1 d . . .
H47 H 0.5096 0.7979 0.7184 0.083 Uiso 1 1 calc R . .
C48 C 0.6258(4) 0.6982(4) 0.7494(3) 0.0563(13) Uani 1 1 d . . .
C49 C 0.5598(4) 0.6333(3) 0.8011(3) 0.0525(13) Uani 1 1 d . . .
C50 C 0.6095(4) 0.5608(3) 0.8493(3) 0.0517(12) Uani 1 1 d . . .
H50 H 0.6837 0.5535 0.8492 0.062 Uiso 1 1 calc R . .
C51 C 0.5495(4) 0.4990(3) 0.8977(3) 0.0514(12) Uani 1 1 d . . .
C52 C 0.4375(4) 0.5106(3) 0.8971(3) 0.0542(13) Uani 1 1 d . . .
C53 C 0.3853(4) 0.5823(4) 0.8485(3) 0.0663(16) Uani 1 1 d . . .
H53 H 0.3112 0.5889 0.8479 0.080 Uiso 1 1 calc R . .
C54 C 0.4477(4) 0.6433(4) 0.8012(3) 0.0631(15) Uani 1 1 d . . .
H54 H 0.4147 0.6923 0.7685 0.076 Uiso 1 1 calc R . .
C55 C 0.5748(4) 0.4183(3) 0.9540(3) 0.0538(13) Uani 1 1 d . . .
C56 C 0.6688(5) 0.3719(4) 0.9805(3) 0.0740(18) Uani 1 1 d . . .
H56 H 0.7345 0.3923 0.9610 0.089 Uiso 1 1 calc R . .
C57 C 0.6632(6) 0.2944(4) 1.0367(4) 0.084(2) Uani 1 1 d . . .
H57 H 0.7259 0.2623 1.0548 0.100 Uiso 1 1 calc R . .
C58 C 0.5660(6) 0.2639(4) 1.0663(3) 0.0753(18) Uani 1 1 d . . .
H58 H 0.5648 0.2124 1.1047 0.090 Uiso 1 1 calc R . .
C59 C 0.4718(5) 0.3072(4) 1.0408(3) 0.0653(15) Uani 1 1 d . . .
H59 H 0.4067 0.2857 1.0605 0.078 Uiso 1 1 calc R . .
C60 C 0.4772(4) 0.3854(3) 0.9836(3) 0.0554(13) Uani 1 1 d . . .
C61 C 0.2823(5) 0.4246(4) 0.9636(3) 0.0728(18) Uani 1 1 d . . .
H61A H 0.2405 0.4803 0.9460 0.087 Uiso 1 1 calc R . .
H61B H 0.2703 0.4004 1.0126 0.087 Uiso 1 1 calc R . .
C62 C 0.2441(5) 0.3600(5) 0.9323(3) 0.0776(19) Uani 1 1 d . . .
H62A H 0.2903 0.3064 0.9470 0.093 Uiso 1 1 calc R . .
H62B H 0.1726 0.3438 0.9496 0.093 Uiso 1 1 calc R . .
C63 C 0.2429(5) 0.3964(5) 0.8552(4) 0.0805(19) Uani 1 1 d . . .
H63A H 0.1901 0.4457 0.8405 0.097 Uiso 1 1 calc R . .
H63B H 0.3121 0.4192 0.8379 0.097 Uiso 1 1 calc R . .
C64 C 0.2181(5) 0.3294(5) 0.8257(4) 0.087(2) Uani 1 1 d . . .
H64A H 0.1496 0.3057 0.8439 0.104 Uiso 1 1 calc R . .
H64B H 0.2718 0.2807 0.8397 0.104 Uiso 1 1 calc R . .
C65 C 0.2145(7) 0.3661(7) 0.7492(5) 0.118(3) Uani 1 1 d . . .
H65A H 0.2808 0.3944 0.7314 0.141 Uiso 1 1 calc R . .
H65B H 0.1569 0.4115 0.7356 0.141 Uiso 1 1 calc R . .
C66 C 0.1978(10) 0.2955(10) 0.7168(6) 0.180(5) Uani 1 1 d . . .
H66A H 0.1956 0.3236 0.6682 0.271 Uiso 1 1 calc R . .
H66B H 0.1318 0.2677 0.7336 0.271 Uiso 1 1 calc R . .
H66C H 0.2558 0.2514 0.7286 0.271 Uiso 1 1 calc R . .
C67 C 1.1276(5) 0.8088(5) 0.6192(3) 0.0668(16) Uani 1 1 d . . .
C68 C 1.1356(6) 0.6580(5) 0.6770(4) 0.090(2) Uani 1 1 d . . .
H68 H 1.1028 0.6069 0.7044 0.108 Uiso 1 1 calc R . .
C69 C 1.2430(7) 0.6509(8) 0.6577(5) 0.122(3) Uani 1 1 d . . .
H69 H 1.2807 0.5961 0.6715 0.146 Uiso 1 1 calc R . .
C70 C 1.2910(7) 0.7259(8) 0.6184(5) 0.124(3) Uani 1 1 d . . .
H70 H 1.3624 0.7225 0.6053 0.149 Uiso 1 1 calc R . .
C71 C 1.2347(6) 0.8073(7) 0.5976(4) 0.093(2) Uani 1 1 d . . .
C72 C 1.2798(7) 0.8904(8) 0.5574(5) 0.118(3) Uani 1 1 d . . .
H72 H 1.3495 0.8901 0.5405 0.141 Uiso 1 1 calc R . .
C73 C 1.2243(8) 0.9675(8) 0.5441(4) 0.116(3) Uani 1 1 d . . .
H73 H 1.2567 1.0199 0.5192 0.139 Uiso 1 1 calc R . .
C74 C 1.1176(6) 0.9715(6) 0.5668(3) 0.085(2) Uani 1 1 d . . .
C75 C 1.0575(8) 1.0501(6) 0.5545(4) 0.100(3) Uani 1 1 d . . .
H75 H 1.0878 1.1037 0.5301 0.120 Uiso 1 1 calc R . .
C76 C 0.9554(7) 1.0504(5) 0.5776(4) 0.093(2) Uani 1 1 d . . .
H76 H 0.9154 1.1034 0.5703 0.112 Uiso 1 1 calc R . .
C77 C 0.9110(6) 0.9675(4) 0.6131(3) 0.0765(18) Uani 1 1 d . . .
H77 H 0.8405 0.9671 0.6287 0.092 Uiso 1 1 calc R . .
C78 C 1.0685(5) 0.8913(4) 0.6032(3) 0.0650(16) Uani 1 1 d . . .
C23' C 0.9714(19) 0.590(2) 0.9035(17) 0.054(6) Uani 0.31(3) 1 d PDU A 2
Eu1 Eu 0.87435(2) 0.743068(16) 0.683821(12) 0.04653(10) Uani 1 1 d . . .
F1 F 1.0094(11) 0.7351(6) 0.4577(4) 0.254(5) Uani 1 1 d U . .
F2 F 0.9229(9) 0.6306(4) 0.4538(3) 0.242(4) Uani 1 1 d U . .
F3 F 0.8487(11) 0.7560(6) 0.4440(3) 0.243(5) Uani 1 1 d U . .
F4 F 1.0959(8) 0.6095(15) 0.8984(8) 0.131(5) Uani 0.69(3) 1 d PD A 1
F5 F 0.982(3) 0.5227(6) 0.8947(7) 0.130(9) Uani 0.69(3) 1 d PD A 1
F6 F 0.9580(15) 0.5890(13) 0.9630(7) 0.105(6) Uani 0.69(3) 1 d PD A 1
F7 F 0.4782(4) 0.9410(3) 0.6399(3) 0.151(2) Uani 1 1 d . . .
F8 F 0.6297(4) 0.9975(3) 0.6099(3) 0.136(2) Uani 1 1 d . . .
F9 F 0.5590(4) 0.9352(4) 0.5514(3) 0.150(2) Uani 1 1 d . . .
F4' F 1.062(4) 0.559(3) 0.8874(10) 0.109(13) Uani 0.31(3) 1 d PD A 2
F5' F 0.905(3) 0.5274(16) 0.917(2) 0.134(11) Uani 0.31(3) 1 d PD A 2
F6' F 0.998(5) 0.604(3) 0.9581(18) 0.133(18) Uani 0.31(3) 1 d PD A 2
N1 N 0.8964(4) 0.1812(3) 0.8176(3) 0.0706(14) Uani 1 1 d . . .
N2 N 0.6028(4) 1.0583(3) 0.9157(3) 0.0754(15) Uani 1 1 d . A .
N3 N 0.3947(3) 0.4412(3) 0.9491(2) 0.0593(12) Uani 1 1 d . . .
N4 N 0.9647(4) 0.8909(3) 0.6251(2) 0.0617(12) Uani 1 1 d . A .
N5 N 1.0790(4) 0.7342(3) 0.6580(2) 0.0656(13) Uani 1 1 d . A .
O1 O 0.8891(4) 0.7331(3) 0.57284(18) 0.0729(11) Uani 1 1 d . A .
O2 O 0.8973(3) 0.5934(2) 0.69593(18) 0.0612(10) Uani 1 1 d . A .
O3 O 0.9588(3) 0.6755(2) 0.78772(17) 0.0581(9) Uani 1 1 d . A .
O4 O 0.8255(3) 0.8281(2) 0.75529(17) 0.0538(9) Uani 1 1 d . A .
O5 O 0.7268(3) 0.8346(3) 0.63083(19) 0.0654(10) Uani 1 1 d . A .
O6 O 0.7222(3) 0.6762(2) 0.74328(19) 0.0597(9) 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
C1 0.400(11) 0.091(5) 0.071(5) -0.029(5) 0.038(7) -0.058(7)
C2 0.317(11) 0.066(4) 0.044(4) -0.024(3) 0.029(5) -0.056(6)
C3 0.190(9) 0.061(4) 0.062(4) -0.024(3) 0.022(5) -0.030(5)
C4 0.075(4) 0.053(3) 0.053(3) -0.020(3) 0.011(3) -0.011(3)
C5 0.074(4) 0.047(3) 0.059(3) -0.020(3) 0.009(3) -0.010(3)
C6 0.068(3) 0.046(3) 0.062(4) -0.022(3) 0.008(3) -0.010(3)
C7 0.056(3) 0.046(3) 0.069(4) -0.016(3) 0.005(3) -0.006(2)
C8 0.061(3) 0.050(3) 0.081(4) -0.025(3) 0.002(3) -0.004(3)
C9 0.092(5) 0.057(4) 0.086(5) -0.038(4) 0.001(4) -0.008(3)
C10 0.099(5) 0.058(4) 0.062(4) -0.020(3) 0.002(3) -0.007(3)
C11 0.052(3) 0.048(3) 0.067(4) -0.012(3) 0.003(3) -0.004(2)
C12 0.062(3) 0.057(4) 0.075(4) -0.015(3) 0.003(3) -0.002(3)
C13 0.081(4) 0.076(5) 0.068(4) -0.009(4) -0.001(3) 0.005(4)
C14 0.086(5) 0.064(5) 0.088(5) 0.007(4) 0.008(4) 0.004(4)
C15 0.072(4) 0.049(4) 0.106(6) -0.003(4) 0.005(4) -0.001(3)
C16 0.052(3) 0.050(3) 0.083(4) -0.013(3) 0.005(3) -0.002(3)
C17 0.098(5) 0.056(4) 0.118(6) -0.039(4) 0.011(4) -0.011(4)
C18 0.119(7) 0.085(6) 0.187(10) -0.067(7) 0.019(7) -0.012(5)
C19 0.108(6) 0.087(6) 0.149(8) -0.045(6) -0.009(6) 0.003(5)
C20 0.148(9) 0.139(9) 0.191(11) -0.107(9) -0.019(8) 0.040(8)
C21 0.159(11) 0.184(13) 0.175(12) -0.043(10) 0.004(9) 0.054(10)
C22 0.159(10) 0.265(16) 0.146(10) -0.101(11) -0.053(8) 0.105(11)
C23 0.096(10) 0.063(8) 0.054(7) -0.014(7) -0.004(7) 0.022(8)
C24 0.059(3) 0.042(3) 0.040(3) -0.009(2) -0.002(2) 0.002(2)
C25 0.071(3) 0.043(3) 0.039(3) -0.008(2) 0.007(2) 0.003(2)
C26 0.053(3) 0.039(3) 0.054(3) -0.014(2) 0.001(2) -0.005(2)
C27 0.058(3) 0.037(3) 0.054(3) -0.011(2) 0.002(2) 0.000(2)
C28 0.057(3) 0.041(3) 0.056(3) -0.011(2) 0.004(2) 0.000(2)
C29 0.057(3) 0.046(3) 0.064(3) -0.018(3) 0.007(3) -0.005(2)
C30 0.057(3) 0.057(4) 0.082(4) -0.028(3) 0.007(3) 0.004(3)
C31 0.069(4) 0.056(4) 0.083(5) -0.019(3) -0.009(3) 0.017(3)
C32 0.070(4) 0.053(3) 0.068(4) -0.018(3) -0.011(3) 0.005(3)
C33 0.064(3) 0.054(3) 0.073(4) -0.028(3) 0.012(3) -0.011(3)
C34 0.078(4) 0.068(4) 0.072(4) -0.031(3) 0.012(3) -0.010(3)
C35 0.098(5) 0.091(5) 0.080(5) -0.041(4) 0.003(4) -0.011(4)
C36 0.097(5) 0.109(6) 0.117(7) -0.080(6) 0.019(5) -0.015(5)
C37 0.084(5) 0.082(5) 0.121(7) -0.064(5) 0.002(4) 0.005(4)
C38 0.065(4) 0.059(4) 0.093(5) -0.041(4) 0.009(3) -0.005(3)
C39 0.069(4) 0.060(4) 0.124(6) -0.039(4) 0.000(4) 0.015(3)
C40 0.066(4) 0.068(4) 0.135(7) -0.036(5) 0.000(4) 0.012(3)
C41 0.083(5) 0.068(4) 0.135(7) -0.033(5) 0.002(5) 0.008(4)
C42 0.096(6) 0.078(5) 0.137(7) -0.032(5) 0.017(5) 0.000(4)
C43 0.117(7) 0.074(5) 0.138(8) -0.019(5) -0.002(6) 0.001(5)
C44 0.153(10) 0.125(9) 0.169(11) -0.028(8) 0.013(8) -0.008(7)
C45 0.062(4) 0.090(6) 0.108(7) 0.032(5) -0.004(4) -0.003(4)
C46 0.060(4) 0.060(4) 0.060(4) -0.004(3) -0.012(3) -0.004(3)
C47 0.059(3) 0.057(4) 0.070(4) 0.002(3) 0.008(3) -0.005(3)
C48 0.059(3) 0.053(3) 0.054(3) -0.014(3) 0.008(3) -0.013(3)
C49 0.057(3) 0.045(3) 0.053(3) -0.014(2) 0.010(2) -0.006(2)
C50 0.049(3) 0.044(3) 0.058(3) -0.014(2) 0.008(2) -0.006(2)
C51 0.051(3) 0.048(3) 0.052(3) -0.014(2) 0.007(2) -0.006(2)
C52 0.053(3) 0.050(3) 0.055(3) -0.013(3) 0.010(2) -0.006(2)
C53 0.048(3) 0.055(3) 0.080(4) -0.006(3) 0.007(3) 0.000(3)
C54 0.056(3) 0.052(3) 0.068(4) -0.006(3) 0.006(3) 0.000(3)
C55 0.055(3) 0.050(3) 0.054(3) -0.016(2) 0.008(2) -0.005(2)
C56 0.059(4) 0.070(4) 0.077(4) -0.008(3) 0.003(3) 0.001(3)
C57 0.082(5) 0.070(4) 0.079(5) -0.004(4) -0.011(4) 0.011(4)
C58 0.097(5) 0.054(4) 0.061(4) -0.006(3) 0.005(4) -0.002(3)
C59 0.078(4) 0.057(3) 0.056(3) -0.014(3) 0.009(3) -0.012(3)
C60 0.066(3) 0.043(3) 0.054(3) -0.013(2) 0.006(3) -0.005(3)
C61 0.054(3) 0.074(4) 0.074(4) -0.007(3) 0.024(3) -0.010(3)
C62 0.055(3) 0.084(5) 0.078(4) -0.008(4) 0.010(3) -0.019(3)
C63 0.063(4) 0.082(5) 0.084(5) -0.014(4) 0.007(3) -0.007(3)
C64 0.066(4) 0.100(5) 0.087(5) -0.021(4) 0.000(4) -0.016(4)
C65 0.096(6) 0.144(8) 0.112(7) -0.042(6) -0.005(5) -0.017(6)
C66 0.164(11) 0.255(16) 0.162(11) -0.116(12) -0.003(9) -0.047(11)
C67 0.063(4) 0.091(5) 0.046(3) -0.021(3) 0.008(3) -0.025(3)
C68 0.073(4) 0.096(6) 0.093(5) -0.026(4) 0.008(4) 0.003(4)
C69 0.075(5) 0.148(9) 0.137(8) -0.049(7) 0.016(5) 0.016(6)
C70 0.062(5) 0.177(11) 0.133(8) -0.059(8) 0.029(5) -0.009(6)
C71 0.069(4) 0.134(7) 0.078(5) -0.036(5) 0.019(4) -0.029(5)
C72 0.082(6) 0.169(10) 0.098(7) -0.037(7) 0.036(5) -0.056(6)
C73 0.115(7) 0.151(9) 0.078(5) -0.029(6) 0.032(5) -0.083(7)
C74 0.102(5) 0.096(6) 0.050(4) -0.013(4) 0.010(4) -0.049(5)
C75 0.143(8) 0.080(6) 0.067(5) -0.005(4) 0.000(5) -0.059(6)
C76 0.128(7) 0.056(4) 0.078(5) 0.001(3) -0.010(5) -0.028(4)
C77 0.095(5) 0.058(4) 0.065(4) -0.005(3) -0.003(3) -0.022(4)
C78 0.073(4) 0.080(4) 0.039(3) -0.013(3) 0.008(3) -0.033(3)
C23' 0.063(9) 0.049(10) 0.045(10) -0.014(8) 0.002(8) 0.012(8)
Eu1 0.05400(16) 0.04072(15) 0.03793(15) -0.00518(10) 0.00345(10) -0.00715(10)
F1 0.458(13) 0.174(7) 0.123(5) -0.050(5) 0.150(7) -0.100(8)
F2 0.540(13) 0.123(5) 0.075(4) -0.048(3) 0.042(6) -0.059(7)
F3 0.482(14) 0.158(6) 0.074(4) -0.013(4) -0.081(6) -0.017(8)
F4 0.085(6) 0.144(12) 0.135(10) -0.018(8) -0.034(5) 0.038(7)
F5 0.24(2) 0.048(5) 0.098(8) -0.022(5) -0.059(12) 0.036(9)
F6 0.148(9) 0.091(9) 0.044(6) 0.004(5) 0.012(6) 0.056(7)
F7 0.089(3) 0.108(4) 0.171(5) 0.043(3) 0.026(3) 0.034(3)
F8 0.105(3) 0.060(3) 0.192(5) 0.020(3) -0.012(3) -0.001(2)
F9 0.111(4) 0.167(5) 0.098(4) 0.045(3) -0.037(3) 0.001(3)
F4' 0.13(2) 0.11(3) 0.064(10) -0.015(14) -0.009(15) 0.087(18)
F5' 0.115(18) 0.059(11) 0.17(2) 0.031(12) -0.010(16) 0.012(11)
F6' 0.26(4) 0.084(16) 0.07(2) -0.041(17) -0.10(3) 0.06(2)
N1 0.074(3) 0.038(3) 0.098(4) -0.023(3) 0.006(3) -0.007(2)
N2 0.065(3) 0.059(3) 0.107(5) -0.040(3) 0.003(3) 0.013(2)
N3 0.052(3) 0.055(3) 0.060(3) -0.007(2) 0.015(2) -0.010(2)
N4 0.074(3) 0.056(3) 0.043(2) -0.001(2) 0.000(2) -0.017(2)
N5 0.061(3) 0.071(3) 0.058(3) -0.015(3) 0.008(2) -0.005(3)
O1 0.110(3) 0.061(3) 0.041(2) -0.0087(19) 0.002(2) -0.014(2)
O2 0.084(3) 0.047(2) 0.051(2) -0.0146(18) 0.0032(19) -0.0028(19)
O3 0.067(2) 0.060(2) 0.042(2) -0.0146(17) -0.0027(17) 0.0127(18)
O4 0.071(2) 0.0410(19) 0.041(2) -0.0060(15) -0.0019(17) 0.0005(16)
O5 0.056(2) 0.065(2) 0.055(2) 0.0036(19) -0.0022(18) -0.0080(19)
O6 0.056(2) 0.046(2) 0.066(2) -0.0072(18) 0.0124(18) -0.0093(17)

_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 F2 1.292(12) . ?
C1 F3 1.295(19) . ?
C1 F1 1.36(2) . ?
C1 C2 1.505(12) . ?
C2 O1 1.264(8) . ?
C2 C3 1.340(10) . ?
C3 C4 1.386(9) . ?
C3 H3 0.9300 . ?
C4 O2 1.243(6) . ?
C4 C5 1.484(8) . ?
C5 C6 1.386(8) . ?
C5 C10 1.406(8) . ?
C6 C7 1.386(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.417(8) . ?
C7 C11 1.443(8) . ?
C8 C9 1.378(9) . ?
C8 N1 1.380(7) . ?
C9 C10 1.372(8) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.380(8) . ?
C11 C16 1.397(8) . ?
C12 C13 1.380(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.387(10) . ?
C13 H13 0.9300 . ?
C14 C15 1.343(10) . ?
C14 H14 0.9300 . ?
C15 C16 1.394(9) . ?
C15 H15 0.9300 . ?
C16 N1 1.391(8) . ?
C17 N1 1.444(8) . ?
C17 C18 1.560(11) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.419(11) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.521(12) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.396(15) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.454(14) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 F4 1.294(9) . ?
C23 F5 1.307(9) . ?
C23 F6 1.311(9) . ?
C23 C24 1.527(17) . ?
C24 O3 1.250(6) . ?
C24 C25 1.375(7) . ?
C24 C23' 1.51(4) . ?
C25 C26 1.418(7) . ?
C25 H25 0.9300 . ?
C26 O4 1.261(6) . ?
C26 C27 1.483(7) . ?
C27 C28 1.386(7) . ?
C27 C32 1.413(7) . ?
C28 C29 1.387(7) . ?
C28 H28 0.9300 . ?
C29 C30 1.415(8) . ?
C29 C33 1.444(8) . ?
C30 C31 1.376(9) . ?
C30 N2 1.378(7) . ?
C31 C32 1.375(8) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
C33 C34 1.379(9) . ?
C33 C38 1.409(8) . ?
C34 C35 1.367(9) . ?
C34 H34 0.9300 . ?
C35 C36 1.373(10) . ?
C35 H35 0.9300 . ?
C36 C37 1.375(11) . ?
C36 H36 0.9300 . ?
C37 C38 1.364(9) . ?
C37 H37 0.9300 . ?
C38 N2 1.386(8) . ?
C39 N2 1.452(8) . ?
C39 C40 1.518(10) . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C40 C41 1.516(9) . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C41 C42 1.487(10) . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C42 C43 1.514(10) . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C43 C44 1.496(12) . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?
C45 F7 1.312(9) . ?
C45 F8 1.317(9) . ?
C45 F9 1.331(11) . ?
C45 C46 1.526(9) . ?
C46 O5 1.269(7) . ?
C46 C47 1.377(8) . ?
C47 C48 1.427(8) . ?
C47 H47 0.9300 . ?
C48 O6 1.254(6) . ?
C48 C49 1.479(7) . ?
C49 C50 1.379(7) . ?
C49 C54 1.405(7) . ?
C50 C51 1.379(7) . ?
C50 H50 0.9300 . ?
C51 C52 1.406(7) . ?
C51 C55 1.441(7) . ?
C52 N3 1.375(6) . ?
C52 C53 1.389(7) . ?
C53 C54 1.380(8) . ?
C53 H53 0.9300 . ?
C54 H54 0.9300 . ?
C55 C56 1.382(8) . ?
C55 C60 1.397(7) . ?
C56 C57 1.384(8) . ?
C56 H56 0.9300 . ?
C57 C58 1.382(9) . ?
C57 H57 0.9300 . ?
C58 C59 1.361(9) . ?
C58 H58 0.9300 . ?
C59 C60 1.402(7) . ?
C59 H59 0.9300 . ?
C60 N3 1.374(7) . ?
C61 N3 1.452(7) . ?
C61 C62 1.526(9) . ?
C61 H61A 0.9700 . ?
C61 H61B 0.9700 . ?
C62 C63 1.515(9) . ?
C62 H62A 0.9700 . ?
C62 H62B 0.9700 . ?
C63 C64 1.480(10) . ?
C63 H63A 0.9700 . ?
C63 H63B 0.9700 . ?
C64 C65 1.505(11) . ?
C64 H64A 0.9700 . ?
C64 H64B 0.9700 . ?
C65 C66 1.550(13) . ?
C65 H65A 0.9700 . ?
C65 H65B 0.9700 . ?
C66 H66A 0.9600 . ?
C66 H66B 0.9600 . ?
C66 H66C 0.9600 . ?
C67 N5 1.355(7) . ?
C67 C71 1.401(9) . ?
C67 C78 1.418(9) . ?
C68 N5 1.319(8) . ?
C68 C69 1.400(10) . ?
C68 H68 0.9300 . ?
C69 C70 1.360(13) . ?
C69 H69 0.9300 . ?
C70 C71 1.383(12) . ?
C70 H70 0.9300 . ?
C71 C72 1.443(12) . ?
C72 C73 1.330(13) . ?
C72 H72 0.9300 . ?
C73 C74 1.407(12) . ?
C73 H73 0.9300 . ?
C74 C75 1.382(11) . ?
C74 C78 1.413(9) . ?
C75 C76 1.350(11) . ?
C75 H75 0.9300 . ?
C76 C77 1.417(9) . ?
C76 H76 0.9300 . ?
C77 N4 1.316(8) . ?
C77 H77 0.9300 . ?
C78 N4 1.361(7) . ?
C23' F4' 1.298(10) . ?
C23' F6' 1.303(10) . ?
C23' F5' 1.303(10) . ?
Eu1 O3 2.332(3) . ?
Eu1 O2 2.337(4) . ?
Eu1 O6 2.338(3) . ?
Eu1 O5 2.347(4) . ?
Eu1 O1 2.395(4) . ?
Eu1 O4 2.409(4) . ?
Eu1 N4 2.573(4) . ?
Eu1 N5 2.607(5) . ?

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
F2 C1 F3 109.9(13) . . ?
F2 C1 F1 104.0(14) . . ?
F3 C1 F1 100.3(10) . . ?
F2 C1 C2 116.8(9) . . ?
F3 C1 C2 114.6(14) . . ?
F1 C1 C2 109.4(13) . . ?
O1 C2 C3 130.5(7) . . ?
O1 C2 C1 112.0(7) . . ?
C3 C2 C1 117.5(8) . . ?
C2 C3 C4 124.2(7) . . ?
C2 C3 H3 117.9 . . ?
C4 C3 H3 117.9 . . ?
O2 C4 C3 121.0(6) . . ?
O2 C4 C5 117.0(5) . . ?
C3 C4 C5 121.9(6) . . ?
C6 C5 C10 119.5(5) . . ?
C6 C5 C4 118.9(5) . . ?
C10 C5 C4 121.7(5) . . ?
C5 C6 C7 119.7(5) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C6 C7 C8 119.2(5) . . ?
C6 C7 C11 133.9(6) . . ?
C8 C7 C11 106.9(5) . . ?
C9 C8 N1 130.0(6) . . ?
C9 C8 C7 121.7(5) . . ?
N1 C8 C7 108.4(5) . . ?
C10 C9 C8 117.9(6) . . ?
C10 C9 H9 121.0 . . ?
C8 C9 H9 121.0 . . ?
C9 C10 C5 122.1(6) . . ?
C9 C10 H10 119.0 . . ?
C5 C10 H10 119.0 . . ?
C12 C11 C16 118.7(6) . . ?
C12 C11 C7 134.7(5) . . ?
C16 C11 C7 106.6(5) . . ?
C11 C12 C13 119.0(6) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C12 C13 C14 120.4(7) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 122.4(7) . . ?
C15 C14 H14 118.8 . . ?
C13 C14 H14 118.8 . . ?
C14 C15 C16 117.0(7) . . ?
C14 C15 H15 121.5 . . ?
C16 C15 H15 121.5 . . ?
N1 C16 C15 128.4(6) . . ?
N1 C16 C11 109.2(5) . . ?
C15 C16 C11 122.4(7) . . ?
N1 C17 C18 110.2(6) . . ?
N1 C17 H17A 109.6 . . ?
C18 C17 H17A 109.6 . . ?
N1 C17 H17B 109.6 . . ?
C18 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
C19 C18 C17 113.3(7) . . ?
C19 C18 H18A 108.9 . . ?
C17 C18 H18A 108.9 . . ?
C19 C18 H18B 108.9 . . ?
C17 C18 H18B 108.9 . . ?
H18A C18 H18B 107.7 . . ?
C18 C19 C20 113.7(8) . . ?
C18 C19 H19A 108.8 . . ?
C20 C19 H19A 108.8 . . ?
C18 C19 H19B 108.8 . . ?
C20 C19 H19B 108.8 . . ?
H19A C19 H19B 107.7 . . ?
C21 C20 C19 114.8(11) . . ?
C21 C20 H20A 108.6 . . ?
C19 C20 H20A 108.6 . . ?
C21 C20 H20B 108.6 . . ?
C19 C20 H20B 108.6 . . ?
H20A C20 H20B 107.5 . . ?
C20 C21 C22 113.7(13) . . ?
C20 C21 H21A 108.8 . . ?
C22 C21 H21A 108.8 . . ?
C20 C21 H21B 108.8 . . ?
C22 C21 H21B 108.8 . . ?
H21A C21 H21B 107.7 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
F4 C23 F5 107.0(13) . . ?
F4 C23 F6 109.1(13) . . ?
F5 C23 F6 105.1(15) . . ?
F4 C23 C24 112.2(11) . . ?
F5 C23 C24 110.4(10) . . ?
F6 C23 C24 112.7(12) . . ?
O3 C24 C25 128.9(5) . . ?
O3 C24 C23' 115.2(10) . . ?
C25 C24 C23' 115.4(10) . . ?
O3 C24 C23 112.6(6) . . ?
C25 C24 C23 118.4(6) . . ?
C23' C24 C23 12.1(10) . . ?
C24 C25 C26 123.1(5) . . ?
C24 C25 H25 118.4 . . ?
C26 C25 H25 118.4 . . ?
O4 C26 C25 122.5(5) . . ?
O4 C26 C27 118.0(4) . . ?
C25 C26 C27 119.5(5) . . ?
C28 C27 C32 119.2(5) . . ?
C28 C27 C26 122.1(5) . . ?
C32 C27 C26 118.7(5) . . ?
C27 C28 C29 119.9(5) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 H28 120.0 . . ?
C28 C29 C30 119.4(5) . . ?
C28 C29 C33 133.3(5) . . ?
C30 C29 C33 107.3(5) . . ?
C31 C30 N2 130.4(6) . . ?
C31 C30 C29 121.3(5) . . ?
N2 C30 C29 108.2(6) . . ?
C32 C31 C30 118.5(6) . . ?
C32 C31 H31 120.8 . . ?
C30 C31 H31 120.8 . . ?
C31 C32 C27 121.7(6) . . ?
C31 C32 H32 119.2 . . ?
C27 C32 H32 119.2 . . ?
C34 C33 C38 119.4(6) . . ?
C34 C33 C29 134.5(6) . . ?
C38 C33 C29 106.0(5) . . ?
C35 C34 C33 118.5(6) . . ?
C35 C34 H34 120.7 . . ?
C33 C34 H34 120.7 . . ?
C34 C35 C36 121.0(7) . . ?
C34 C35 H35 119.5 . . ?
C36 C35 H35 119.5 . . ?
C35 C36 C37 122.0(7) . . ?
C35 C36 H36 119.0 . . ?
C37 C36 H36 119.0 . . ?
C38 C37 C36 117.1(7) . . ?
C38 C37 H37 121.5 . . ?
C36 C37 H37 121.5 . . ?
C37 C38 N2 129.0(6) . . ?
C37 C38 C33 121.9(7) . . ?
N2 C38 C33 109.1(5) . . ?
N2 C39 C40 112.6(5) . . ?
N2 C39 H39A 109.1 . . ?
C40 C39 H39A 109.1 . . ?
N2 C39 H39B 109.1 . . ?
C40 C39 H39B 109.1 . . ?
H39A C39 H39B 107.8 . . ?
C41 C40 C39 112.8(6) . . ?
C41 C40 H40A 109.0 . . ?
C39 C40 H40A 109.0 . . ?
C41 C40 H40B 109.0 . . ?
C39 C40 H40B 109.0 . . ?
H40A C40 H40B 107.8 . . ?
C42 C41 C40 115.1(6) . . ?
C42 C41 H41A 108.5 . . ?
C40 C41 H41A 108.5 . . ?
C42 C41 H41B 108.5 . . ?
C40 C41 H41B 108.5 . . ?
H41A C41 H41B 107.5 . . ?
C41 C42 C43 114.7(7) . . ?
C41 C42 H42A 108.6 . . ?
C43 C42 H42A 108.6 . . ?
C41 C42 H42B 108.6 . . ?
C43 C42 H42B 108.6 . . ?
H42A C42 H42B 107.6 . . ?
C44 C43 C42 112.9(8) . . ?
C44 C43 H43A 109.0 . . ?
C42 C43 H43A 109.0 . . ?
C44 C43 H43B 109.0 . . ?
C42 C43 H43B 109.0 . . ?
H43A C43 H43B 107.8 . . ?
C43 C44 H44A 109.5 . . ?
C43 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C43 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
F7 C45 F8 108.5(8) . . ?
F7 C45 F9 105.8(7) . . ?
F8 C45 F9 104.8(6) . . ?
F7 C45 C46 115.3(6) . . ?
F8 C45 C46 111.5(6) . . ?
F9 C45 C46 110.3(8) . . ?
O5 C46 C47 130.1(5) . . ?
O5 C46 C45 113.1(5) . . ?
C47 C46 C45 116.9(6) . . ?
C46 C47 C48 122.6(6) . . ?
C46 C47 H47 118.7 . . ?
C48 C47 H47 118.7 . . ?
O6 C48 C47 122.3(5) . . ?
O6 C48 C49 117.6(5) . . ?
C47 C48 C49 120.1(5) . . ?
C50 C49 C54 119.6(5) . . ?
C50 C49 C48 119.1(5) . . ?
C54 C49 C48 121.3(5) . . ?
C49 C50 C51 120.1(5) . . ?
C49 C50 H50 120.0 . . ?
C51 C50 H50 120.0 . . ?
C50 C51 C52 119.4(5) . . ?
C50 C51 C55 134.3(5) . . ?
C52 C51 C55 106.4(4) . . ?
N3 C52 C53 129.0(5) . . ?
N3 C52 C51 109.2(5) . . ?
C53 C52 C51 121.7(5) . . ?
C54 C53 C52 117.5(5) . . ?
C54 C53 H53 121.3 . . ?
C52 C53 H53 121.3 . . ?
C53 C54 C49 121.8(5) . . ?
C53 C54 H54 119.1 . . ?
C49 C54 H54 119.1 . . ?
C56 C55 C60 119.5(5) . . ?
C56 C55 C51 134.3(5) . . ?
C60 C55 C51 106.2(5) . . ?
C55 C56 C57 118.7(6) . . ?
C55 C56 H56 120.7 . . ?
C57 C56 H56 120.7 . . ?
C58 C57 C56 121.0(6) . . ?
C58 C57 H57 119.5 . . ?
C56 C57 H57 119.5 . . ?
C59 C58 C57 121.8(6) . . ?
C59 C58 H58 119.1 . . ?
C57 C58 H58 119.1 . . ?
C58 C59 C60 117.3(6) . . ?
C58 C59 H59 121.4 . . ?
C60 C59 H59 121.4 . . ?
N3 C60 C55 109.8(4) . . ?
N3 C60 C59 128.5(5) . . ?
C55 C60 C59 121.7(5) . . ?
N3 C61 C62 112.2(5) . . ?
N3 C61 H61A 109.2 . . ?
C62 C61 H61A 109.2 . . ?
N3 C61 H61B 109.2 . . ?
C62 C61 H61B 109.2 . . ?
H61A C61 H61B 107.9 . . ?
C63 C62 C61 114.1(6) . . ?
C63 C62 H62A 108.7 . . ?
C61 C62 H62A 108.7 . . ?
C63 C62 H62B 108.7 . . ?
C61 C62 H62B 108.7 . . ?
H62A C62 H62B 107.6 . . ?
C64 C63 C62 113.2(6) . . ?
C64 C63 H63A 108.9 . . ?
C62 C63 H63A 108.9 . . ?
C64 C63 H63B 108.9 . . ?
C62 C63 H63B 108.9 . . ?
H63A C63 H63B 107.8 . . ?
C63 C64 C65 113.1(7) . . ?
C63 C64 H64A 109.0 . . ?
C65 C64 H64A 109.0 . . ?
C63 C64 H64B 109.0 . . ?
C65 C64 H64B 109.0 . . ?
H64A C64 H64B 107.8 . . ?
C64 C65 C66 114.0(9) . . ?
C64 C65 H65A 108.8 . . ?
C66 C65 H65A 108.8 . . ?
C64 C65 H65B 108.8 . . ?
C66 C65 H65B 108.8 . . ?
H65A C65 H65B 107.6 . . ?
C65 C66 H66A 109.5 . . ?
C65 C66 H66B 109.5 . . ?
H66A C66 H66B 109.5 . . ?
C65 C66 H66C 109.5 . . ?
H66A C66 H66C 109.5 . . ?
H66B C66 H66C 109.5 . . ?
N5 C67 C71 122.3(7) . . ?
N5 C67 C78 118.1(5) . . ?
C71 C67 C78 119.5(6) . . ?
N5 C68 C69 122.7(8) . . ?
N5 C68 H68 118.6 . . ?
C69 C68 H68 118.6 . . ?
C70 C69 C68 118.5(9) . . ?
C70 C69 H69 120.8 . . ?
C68 C69 H69 120.8 . . ?
C69 C70 C71 120.7(8) . . ?
C69 C70 H70 119.7 . . ?
C71 C70 H70 119.7 . . ?
C70 C71 C67 117.4(8) . . ?
C70 C71 C72 124.4(8) . . ?
C67 C71 C72 118.2(9) . . ?
C73 C72 C71 121.6(8) . . ?
C73 C72 H72 119.2 . . ?
C71 C72 H72 119.2 . . ?
C72 C73 C74 121.5(8) . . ?
C72 C73 H73 119.3 . . ?
C74 C73 H73 119.3 . . ?
C75 C74 C73 123.3(8) . . ?
C75 C74 C78 118.0(7) . . ?
C73 C74 C78 118.8(9) . . ?
C76 C75 C74 121.0(7) . . ?
C76 C75 H75 119.5 . . ?
C74 C75 H75 119.5 . . ?
C75 C76 C77 117.9(8) . . ?
C75 C76 H76 121.1 . . ?
C77 C76 H76 121.1 . . ?
N4 C77 C76 123.2(7) . . ?
N4 C77 H77 118.4 . . ?
C76 C77 H77 118.4 . . ?
N4 C78 C74 121.4(7) . . ?
N4 C78 C67 118.3(5) . . ?
C74 C78 C67 120.3(6) . . ?
F4' C23' F6' 100(3) . . ?
F4' C23' F5' 107(3) . . ?
F6' C23' F5' 112(3) . . ?
F4' C23' C24 111(2) . . ?
F6' C23' C24 114(2) . . ?
F5' C23' C24 112(2) . . ?
O3 Eu1 O2 75.44(13) . . ?
O3 Eu1 O6 84.79(13) . . ?
O2 Eu1 O6 74.40(13) . . ?
O3 Eu1 O5 143.87(14) . . ?
O2 Eu1 O5 123.33(14) . . ?
O6 Eu1 O5 73.33(13) . . ?
O3 Eu1 O1 136.60(14) . . ?
O2 Eu1 O1 71.38(13) . . ?
O6 Eu1 O1 111.61(14) . . ?
O5 Eu1 O1 79.05(15) . . ?
O3 Eu1 O4 71.65(12) . . ?
O2 Eu1 O4 137.46(12) . . ?
O6 Eu1 O4 76.46(13) . . ?
O5 Eu1 O4 75.42(13) . . ?
O1 Eu1 O4 149.60(13) . . ?
O3 Eu1 N4 105.70(14) . . ?
O2 Eu1 N4 139.94(15) . . ?
O6 Eu1 N4 145.34(15) . . ?
O5 Eu1 N4 79.79(14) . . ?
O1 Eu1 N4 83.64(14) . . ?
O4 Eu1 N4 75.89(14) . . ?
O3 Eu1 N5 72.60(14) . . ?
O2 Eu1 N5 80.33(15) . . ?
O6 Eu1 N5 149.61(14) . . ?
O5 Eu1 N5 136.11(14) . . ?
O1 Eu1 N5 74.90(16) . . ?
O4 Eu1 N5 113.62(14) . . ?
N4 Eu1 N5 62.86(16) . . ?
C8 N1 C16 108.9(5) . . ?
C8 N1 C17 124.9(6) . . ?
C16 N1 C17 125.8(6) . . ?
C30 N2 C38 109.3(5) . . ?
C30 N2 C39 125.5(6) . . ?
C38 N2 C39 124.9(5) . . ?
C60 N3 C52 108.3(4) . . ?
C60 N3 C61 124.6(5) . . ?
C52 N3 C61 127.0(5) . . ?
C77 N4 C78 118.5(5) . . ?
C77 N4 Eu1 121.1(4) . . ?
C78 N4 Eu1 120.4(4) . . ?
C68 N5 C67 118.5(6) . . ?
C68 N5 Eu1 121.9(4) . . ?
C67 N5 Eu1 119.4(4) . . ?
C2 O1 Eu1 131.1(4) . . ?
C4 O2 Eu1 140.8(4) . . ?
C24 O3 Eu1 131.8(3) . . ?
C26 O4 Eu1 134.1(3) . . ?
C46 O5 Eu1 129.5(3) . . ?
C48 O6 Eu1 137.5(3) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.621
_refine_diff_density_min         -0.611
_refine_diff_density_rms         0.087

# Attachment '- HTHA.cif'

data_060502c
_database_code_depnum_ccdc_archive 'CCDC 838899'
#TrackingRef '- HTHA.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H22 F3 N O2'
_chemical_formula_weight         389.41

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   5.027(2)
_cell_length_b                   14.846(3)
_cell_length_c                   26.355(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.576(2)
_cell_angle_gamma                90.00
_cell_volume                     1964.8(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1252
_cell_measurement_theta_min      2.696
_cell_measurement_theta_max      18.581

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9513
_exptl_absorpt_correction_T_max  0.9797
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8354
_diffrn_reflns_av_R_equivalents  0.1596
_diffrn_reflns_av_sigmaI/netI    0.2323
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3010
_reflns_number_gt                854
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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^)+(0.0619P)^2^+0.0000P] 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     SHELXL
_refine_ls_extinction_coef       0.019(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3010
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2766
_refine_ls_R_factor_gt           0.0959
_refine_ls_wR_factor_ref         0.2361
_refine_ls_wR_factor_gt          0.1870
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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
F1 F 0.7996(13) 0.1443(4) -0.09052(19) 0.145(3) Uani 1 1 d . . .
F2 F 0.8579(13) 0.2411(4) -0.02893(18) 0.145(2) Uani 1 1 d . . .
F3 F 0.5099(15) 0.2552(4) -0.0845(2) 0.161(3) Uani 1 1 d . . .
N1 N 0.0426(13) 0.2145(4) 0.25363(19) 0.0685(17) Uani 1 1 d . . .
O1 O 0.1315(12) 0.0538(3) 0.03355(18) 0.0960(19) Uani 1 1 d . . .
H1 H 0.1734 0.0478 0.0040 0.144 Uiso 1 1 calc R . .
O2 O 0.3542(14) 0.0818(4) -0.04798(18) 0.103(2) Uani 1 1 d . . .
C1 C 0.0731(15) 0.1807(5) 0.2047(2) 0.0638(19) Uani 1 1 d . . .
C2 C -0.0508(16) 0.1082(5) 0.1803(2) 0.069(2) Uani 1 1 d . . .
H2 H -0.1776 0.0734 0.1958 0.082 Uiso 1 1 calc R . .
C3 C 0.0243(16) 0.0910(5) 0.1321(3) 0.072(2) Uani 1 1 d . . .
H3 H -0.0593 0.0441 0.1143 0.086 Uiso 1 1 calc R . .
C4 C 0.2192(16) 0.1398(4) 0.1085(2) 0.0651(19) Uani 1 1 d . . .
C5 C 0.3537(15) 0.2096(4) 0.1336(2) 0.0631(19) Uani 1 1 d . . .
H5 H 0.4937 0.2397 0.1191 0.076 Uiso 1 1 calc R . .
C6 C 0.2705(14) 0.2322(4) 0.1809(2) 0.0595(19) Uani 1 1 d . . .
C7 C 0.3710(15) 0.2987(5) 0.2188(2) 0.0599(19) Uani 1 1 d . . .
C8 C 0.5560(17) 0.3645(4) 0.2175(2) 0.074(2) Uani 1 1 d . . .
H8 H 0.6546 0.3748 0.1891 0.089 Uiso 1 1 calc R . .
C9 C 0.5908(17) 0.4177(4) 0.2633(2) 0.074(2) Uani 1 1 d . . .
H9 H 0.7187 0.4630 0.2649 0.089 Uiso 1 1 calc R . .
C10 C 0.441(2) 0.4029(6) 0.3037(3) 0.090(3) Uani 1 1 d . . .
H10 H 0.4709 0.4387 0.3324 0.108 Uiso 1 1 calc R . .
C11 C 0.2476(18) 0.3383(5) 0.3049(2) 0.074(2) Uani 1 1 d . . .
H11 H 0.1476 0.3291 0.3333 0.089 Uiso 1 1 calc R . .
C12 C 0.2103(17) 0.2871(5) 0.2607(2) 0.069(2) Uani 1 1 d . . .
C13 C 0.2734(17) 0.1157(5) 0.0549(3) 0.072(2) Uani 1 1 d . . .
C14 C 0.4652(16) 0.1593(5) 0.0254(2) 0.075(2) Uani 1 1 d . . .
H14 H 0.5759 0.2029 0.0405 0.090 Uiso 1 1 calc R . .
C15 C 0.4890(17) 0.1391(5) -0.0230(3) 0.077(2) Uani 1 1 d . . .
C16 C 0.663(2) 0.1952(7) -0.0564(3) 0.103(3) Uani 1 1 d . . .
C17 C -0.1444(16) 0.1750(5) 0.2881(3) 0.085(3) Uani 1 1 d . . .
H17A H -0.2903 0.1472 0.2685 0.103 Uiso 1 1 calc R . .
H17B H -0.2179 0.2222 0.3088 0.103 Uiso 1 1 calc R . .
C18 C -0.0118(19) 0.1057(5) 0.3221(3) 0.087(2) Uani 1 1 d . . .
H18A H 0.0722 0.0608 0.3014 0.104 Uiso 1 1 calc R . .
H18B H 0.1264 0.1344 0.3433 0.104 Uiso 1 1 calc R . .
C19 C -0.202(2) 0.0610(5) 0.3548(3) 0.104(3) Uani 1 1 d . . .
H19A H -0.3357 0.0302 0.3333 0.125 Uiso 1 1 calc R . .
H19B H -0.2929 0.1066 0.3739 0.125 Uiso 1 1 calc R . .
C20 C -0.076(2) -0.0062(7) 0.3914(3) 0.128(4) Uani 1 1 d . A .
H20A H 0.0102 -0.0517 0.3714 0.154 Uiso 1 1 calc R . .
H20B H 0.0642 0.0251 0.4109 0.154 Uiso 1 1 calc R . .
C21 C -0.236(2) -0.0521(7) 0.4267(4) 0.152(5) Uani 1 1 d . . .
H21A H -0.3763 -0.0852 0.4084 0.182 Uiso 0.71(7) 1 calc PR A 1
H21B H -0.3186 -0.0085 0.4485 0.182 Uiso 0.71(7) 1 calc PR A 1
H21C H -0.2876 -0.1037 0.4060 0.182 Uiso 0.29(7) 1 d PR A 2
H21D H -0.3908 -0.0131 0.4242 0.182 Uiso 0.29(7) 1 d PR A 2
C22 C -0.064(13) -0.1178(15) 0.4595(11) 0.156(19) Uani 0.71(7) 1 d P A 1
H22A H -0.1738 -0.1472 0.4835 0.235 Uiso 0.71(7) 1 calc PR A 1
H22B H 0.0751 -0.0851 0.4774 0.235 Uiso 0.71(7) 1 calc PR A 1
H22C H 0.0121 -0.1622 0.4381 0.235 Uiso 0.71(7) 1 calc PR A 1
C22' C -0.28(3) -0.094(5) 0.478(3) 0.16(3) Uani 0.29(7) 1 d P A 2
H22D H -0.4695 -0.1034 0.4819 0.241 Uiso 0.29(7) 1 calc PR A 2
H22E H -0.2151 -0.0544 0.5048 0.241 Uiso 0.29(7) 1 calc PR A 2
H22F H -0.1912 -0.1508 0.4812 0.241 Uiso 0.29(7) 1 calc PR A 2

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
F1 0.187(7) 0.173(5) 0.081(3) -0.023(3) 0.054(4) -0.020(5)
F2 0.185(5) 0.184(5) 0.067(3) -0.012(3) 0.018(3) -0.100(5)
F3 0.208(7) 0.150(5) 0.126(4) 0.078(4) 0.016(4) -0.023(5)
N1 0.095(5) 0.068(4) 0.043(3) 0.009(3) 0.012(3) 0.009(4)
O1 0.117(5) 0.106(4) 0.066(3) -0.026(3) 0.018(3) -0.048(4)
O2 0.145(6) 0.100(4) 0.063(3) -0.024(3) 0.000(3) -0.035(4)
C1 0.079(6) 0.062(4) 0.051(4) 0.007(4) 0.002(4) -0.003(4)
C2 0.087(6) 0.063(4) 0.056(4) 0.002(3) 0.002(4) -0.012(4)
C3 0.084(6) 0.067(5) 0.064(5) 0.007(4) 0.001(4) 0.002(5)
C4 0.077(6) 0.056(4) 0.062(4) -0.006(4) 0.001(4) -0.004(4)
C5 0.082(6) 0.064(4) 0.044(4) 0.001(3) 0.017(3) -0.010(4)
C6 0.090(6) 0.048(4) 0.040(4) 0.012(3) -0.006(4) 0.005(4)
C7 0.076(5) 0.061(5) 0.042(4) 0.013(3) -0.005(4) 0.003(4)
C8 0.109(7) 0.057(4) 0.054(4) 0.005(3) -0.012(4) -0.010(5)
C9 0.113(7) 0.057(4) 0.051(4) -0.006(3) -0.012(4) -0.004(4)
C10 0.133(9) 0.084(6) 0.052(5) -0.001(4) -0.008(5) 0.016(6)
C11 0.107(7) 0.064(5) 0.050(4) -0.003(4) 0.001(4) 0.004(5)
C12 0.090(6) 0.065(5) 0.051(4) 0.011(4) -0.001(4) 0.009(5)
C13 0.091(7) 0.069(5) 0.057(4) -0.009(4) 0.000(5) 0.003(4)
C14 0.104(7) 0.074(5) 0.049(4) -0.006(4) 0.008(4) -0.012(5)
C15 0.095(7) 0.081(5) 0.057(5) -0.005(4) 0.012(4) -0.016(5)
C16 0.125(9) 0.117(8) 0.067(5) 0.004(5) -0.002(6) -0.025(7)
C17 0.101(7) 0.090(5) 0.067(5) 0.010(4) 0.022(5) 0.005(5)
C18 0.117(7) 0.086(5) 0.058(4) 0.015(4) 0.012(5) 0.011(5)
C19 0.146(9) 0.077(6) 0.091(6) 0.013(5) 0.012(6) 0.009(6)
C20 0.179(12) 0.115(7) 0.091(6) 0.039(6) 0.013(7) -0.003(7)
C21 0.219(15) 0.127(9) 0.107(7) 0.045(7) -0.025(8) -0.007(9)
C22 0.26(5) 0.096(12) 0.109(14) 0.052(10) -0.02(2) -0.005(17)
C22' 0.22(7) 0.14(4) 0.12(4) 0.04(3) -0.01(5) 0.03(5)

_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
F1 C16 1.382(10) . ?
F2 C16 1.374(9) . ?
F3 C16 1.373(10) . ?
N1 C12 1.375(8) . ?
N1 C1 1.400(8) . ?
N1 C17 1.460(8) . ?
O1 C13 1.278(8) . ?
O1 H1 0.8200 . ?
O2 C15 1.255(8) . ?
C1 C2 1.386(9) . ?
C1 C6 1.421(9) . ?
C2 C3 1.364(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.389(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(9) . ?
C4 C13 1.494(9) . ?
C5 C6 1.373(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.478(8) . ?
C7 C8 1.350(9) . ?
C7 C12 1.408(9) . ?
C8 C9 1.446(9) . ?
C8 H8 0.9300 . ?
C9 C10 1.351(10) . ?
C9 H9 0.9300 . ?
C10 C11 1.366(11) . ?
C10 H10 0.9300 . ?
C11 C12 1.397(9) . ?
C11 H11 0.9300 . ?
C13 C14 1.420(9) . ?
C14 C15 1.323(9) . ?
C14 H14 0.9300 . ?
C15 C16 1.515(10) . ?
C17 C18 1.501(9) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.475(10) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.509(10) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.432(13) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22' 1.53(8) . ?
C21 C22 1.54(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 H21C 0.9700 . ?
C21 H21D 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C22' H22D 0.9600 . ?
C22' H22E 0.9600 . ?
C22' H22F 0.9600 . ?

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
C12 N1 C1 108.4(6) . . ?
C12 N1 C17 129.6(6) . . ?
C1 N1 C17 122.0(6) . . ?
C13 O1 H1 109.5 . . ?
C2 C1 N1 129.9(7) . . ?
C2 C1 C6 121.4(6) . . ?
N1 C1 C6 108.7(6) . . ?
C3 C2 C1 116.1(7) . . ?
C3 C2 H2 121.9 . . ?
C1 C2 H2 121.9 . . ?
C2 C3 C4 123.3(7) . . ?
C2 C3 H3 118.3 . . ?
C4 C3 H3 118.3 . . ?
C3 C4 C5 120.8(6) . . ?
C3 C4 C13 117.5(7) . . ?
C5 C4 C13 121.6(7) . . ?
C6 C5 C4 117.0(7) . . ?
C6 C5 H5 121.5 . . ?
C4 C5 H5 121.5 . . ?
C5 C6 C1 121.0(6) . . ?
C5 C6 C7 131.9(7) . . ?
C1 C6 C7 106.6(5) . . ?
C8 C7 C12 122.0(7) . . ?
C8 C7 C6 132.9(6) . . ?
C12 C7 C6 105.0(6) . . ?
C7 C8 C9 115.5(7) . . ?
C7 C8 H8 122.2 . . ?
C9 C8 H8 122.2 . . ?
C10 C9 C8 121.2(7) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C9 C10 C11 123.7(7) . . ?
C9 C10 H10 118.1 . . ?
C11 C10 H10 118.1 . . ?
C10 C11 C12 115.5(7) . . ?
C10 C11 H11 122.2 . . ?
C12 C11 H11 122.2 . . ?
N1 C12 C11 126.8(7) . . ?
N1 C12 C7 111.0(6) . . ?
C11 C12 C7 121.8(7) . . ?
O1 C13 C14 117.8(6) . . ?
O1 C13 C4 117.8(7) . . ?
C14 C13 C4 124.4(7) . . ?
C15 C14 C13 121.1(7) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
O2 C15 C14 126.1(8) . . ?
O2 C15 C16 112.4(7) . . ?
C14 C15 C16 121.0(8) . . ?
F3 C16 F2 109.4(8) . . ?
F3 C16 F1 106.6(7) . . ?
F2 C16 F1 104.4(8) . . ?
F3 C16 C15 110.4(8) . . ?
F2 C16 C15 112.6(7) . . ?
F1 C16 C15 113.2(8) . . ?
N1 C17 C18 111.5(7) . . ?
N1 C17 H17A 109.3 . . ?
C18 C17 H17A 109.3 . . ?
N1 C17 H17B 109.3 . . ?
C18 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
C19 C18 C17 111.9(8) . . ?
C19 C18 H18A 109.2 . . ?
C17 C18 H18A 109.2 . . ?
C19 C18 H18B 109.2 . . ?
C17 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
C18 C19 C20 113.8(9) . . ?
C18 C19 H19A 108.8 . . ?
C20 C19 H19A 108.8 . . ?
C18 C19 H19B 108.8 . . ?
C20 C19 H19B 108.8 . . ?
H19A C19 H19B 107.7 . . ?
C21 C20 C19 119.8(10) . . ?
C21 C20 H20A 107.4 . . ?
C19 C20 H20A 107.4 . . ?
C21 C20 H20B 107.4 . . ?
C19 C20 H20B 107.4 . . ?
H20A C20 H20B 106.9 . . ?
C20 C21 C22' 153(4) . . ?
C20 C21 C22 110(3) . . ?
C22' C21 C22 49(3) . . ?
C20 C21 H21A 109.6 . . ?
C22' C21 H21A 95.8 . . ?
C22 C21 H21A 109.6 . . ?
C20 C21 H21B 109.6 . . ?
C22' C21 H21B 70.0 . . ?
C22 C21 H21B 109.6 . . ?
H21A C21 H21B 108.1 . . ?
C20 C21 H21C 98.8 . . ?
C22' C21 H21C 97.7 . . ?
C22 C21 H21C 86.9 . . ?
H21A C21 H21C 31.7 . . ?
H21B C21 H21C 138.6 . . ?
C20 C21 H21D 98.3 . . ?
C22' C21 H21D 98.7 . . ?
C22 C21 H21D 147.5 . . ?
H21A C21 H21D 72.9 . . ?
H21B C21 H21D 43.8 . . ?
H21C C21 H21D 103.9 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C22' H22D 109.5 . . ?
C21 C22' H22E 109.5 . . ?
H22D C22' H22E 109.5 . . ?
C21 C22' H22F 109.5 . . ?
H22D C22' H22F 109.5 . . ?
H22E C22' H22F 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.873
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.873
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.050