# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2005


data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Assoc. Prof. Peter C. Junk'
_publ_contact_author_address     
;
School of Chemistry
Monash University
Victoria 3800
Australia
;
_publ_contact_author_email       peter.junk@sci.monash.edu.au
_publ_contact_author_phone       '+61 (0)3 9905 4570'
_publ_contact_author_fax         '+61 (0)3 9905 4597'

_publ_section_title              
;
Steric Engineering of C-F Activation with Lanthanoid
Formamidinates
;
loop_
_publ_author_name
'Peter Junk'
'Marcus L. Cole'
'Glen B. Deacon'
'Kristina Konstas'

data_compound_1
_database_code_depnum_ccdc_archive 'CCDC 253456'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            (La(DippForm)2(F)(THF)).C7H8
_chemical_melting_point          '557 dec.'
_chemical_formula_moiety         'C61 H86 F La N4 O'
_chemical_formula_sum            'C61 H86 F La N4 O'
_chemical_formula_weight         1049.25

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'
La La -0.2871 2.4523 '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_Int_Tables_number      2

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

_cell_length_a                   12.6721(9)
_cell_length_b                   13.6678(12)
_cell_length_c                   17.264(3)
_cell_angle_alpha                92.904(4)
_cell_angle_beta                 104.552(6)
_cell_angle_gamma                91.186(4)
_cell_volume                     2888.8(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       'hexagonal plate'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1108
_exptl_absorpt_coefficient_mu    0.784
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7446
_exptl_absorpt_correction_T_max  0.9258
_exptl_absorpt_process_details   'peformed as part of the DENZO-SMN program'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'psi 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            42471
_diffrn_reflns_av_R_equivalents  0.1285
_diffrn_reflns_av_sigmaI/netI    0.1444
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.28
_diffrn_reflns_theta_max         27.85
_reflns_number_total             13485
_reflns_number_gt                9041
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Nonius Collect'
_computing_cell_refinement       DENZO-SMN
_computing_data_reduction        X-Seed
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-Seed / POV-Ray'
_computing_publication_material  'Microsoft Office 2000'

_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^)+(0.0442P)^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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         13485
_refine_ls_number_parameters     694
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1143
_refine_ls_R_factor_gt           0.0576
_refine_ls_wR_factor_ref         0.1182
_refine_ls_wR_factor_gt          0.1013
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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
La1 La 0.951011(17) 0.646255(16) 0.676118(13) 0.02151(8) Uani 1 1 d . . .
F1 F 1.05903(19) 0.57371(18) 0.61681(14) 0.0447(6) Uani 1 1 d . . .
O1 O 0.8003(2) 0.5711(2) 0.56128(15) 0.0349(7) Uani 1 1 d . B .
N1 N 1.0195(2) 0.8221(2) 0.71506(17) 0.0227(7) Uani 1 1 d . . .
N2 N 0.8943(2) 0.7978(2) 0.59437(17) 0.0258(7) Uani 1 1 d . . .
N3 N 0.8329(2) 0.5700(2) 0.75788(18) 0.0268(7) Uani 1 1 d . . .
N4 N 1.0165(2) 0.5711(2) 0.81207(18) 0.0240(7) Uani 1 1 d . . .
C1 C 1.0982(3) 0.8887(3) 0.7674(2) 0.0240(8) Uani 1 1 d . . .
C2 C 1.2098(3) 0.8767(3) 0.7725(2) 0.0298(9) Uani 1 1 d . . .
C3 C 1.2853(3) 0.9424(3) 0.8237(3) 0.0366(10) Uani 1 1 d . . .
H3 H 1.3610 0.9355 0.8280 0.044 Uiso 1 1 calc R . .
C4 C 1.2519(3) 1.0168(3) 0.8679(3) 0.0406(11) Uani 1 1 d . . .
H4 H 1.3044 1.0608 0.9021 0.049 Uiso 1 1 calc R . .
C5 C 1.1427(3) 1.0273(3) 0.8626(2) 0.0369(10) Uani 1 1 d . . .
H5 H 1.1204 1.0786 0.8935 0.044 Uiso 1 1 calc R . .
C6 C 1.0639(3) 0.9638(3) 0.8127(2) 0.0282(9) Uani 1 1 d . . .
C7 C 1.2479(3) 0.7937(3) 0.7254(3) 0.0353(10) Uani 1 1 d . . .
H7 H 1.1877 0.7775 0.6763 0.042 Uiso 1 1 calc R . .
C8 C 1.2634(4) 0.7027(3) 0.7741(3) 0.0513(13) Uani 1 1 d . . .
H8A H 1.2809 0.6474 0.7417 0.077 Uiso 1 1 calc R . .
H8B H 1.1960 0.6869 0.7897 0.077 Uiso 1 1 calc R . .
H8C H 1.3232 0.7153 0.8224 0.077 Uiso 1 1 calc R . .
C9 C 1.3489(4) 0.8184(4) 0.6976(4) 0.0617(15) Uani 1 1 d . . .
H9A H 1.3388 0.8798 0.6700 0.092 Uiso 1 1 calc R . .
H9B H 1.3611 0.7655 0.6608 0.092 Uiso 1 1 calc R . .
H9C H 1.4121 0.8261 0.7441 0.092 Uiso 1 1 calc R . .
C10 C 0.9438(3) 0.9782(3) 0.8078(2) 0.0322(9) Uani 1 1 d . . .
H10 H 0.9008 0.9249 0.7707 0.039 Uiso 1 1 calc R . .
C11 C 0.9184(4) 0.9707(4) 0.8887(3) 0.0567(14) Uani 1 1 d . . .
H11A H 0.9372 0.9057 0.9086 0.085 Uiso 1 1 calc R . .
H11B H 0.8404 0.9802 0.8831 0.085 Uiso 1 1 calc R . .
H11C H 0.9611 1.0211 0.9268 0.085 Uiso 1 1 calc R . .
C12 C 0.9056(4) 1.0752(4) 0.7746(4) 0.0614(15) Uani 1 1 d . . .
H12A H 0.9453 1.1289 0.8107 0.092 Uiso 1 1 calc R . .
H12B H 0.8272 1.0799 0.7701 0.092 Uiso 1 1 calc R . .
H12C H 0.9195 1.0796 0.7215 0.092 Uiso 1 1 calc R . .
C13 C 0.8550(3) 0.8289(3) 0.5147(2) 0.0300(9) Uani 1 1 d . . .
C14 C 0.7476(3) 0.8625(3) 0.4905(3) 0.0390(11) Uani 1 1 d . . .
C15 C 0.7116(5) 0.8947(3) 0.4133(3) 0.0554(14) Uani 1 1 d . . .
H15 H 0.6394 0.9169 0.3960 0.067 Uiso 1 1 calc R . .
C16 C 0.7780(5) 0.8949(4) 0.3618(3) 0.0634(16) Uani 1 1 d . . .
H16 H 0.7520 0.9189 0.3100 0.076 Uiso 1 1 calc R . .
C17 C 0.8825(5) 0.8606(3) 0.3846(3) 0.0529(13) Uani 1 1 d . . .
H17 H 0.9276 0.8604 0.3482 0.064 Uiso 1 1 calc R . .
C18 C 0.9222(4) 0.8262(3) 0.4611(2) 0.0367(10) Uani 1 1 d . . .
C19 C 0.6762(3) 0.8669(4) 0.5486(3) 0.0488(13) Uani 1 1 d . . .
H19 H 0.7038 0.8184 0.5898 0.059 Uiso 1 1 calc R . .
C20 C 0.5557(4) 0.8396(5) 0.5098(4) 0.082(2) Uani 1 1 d . . .
H20A H 0.5239 0.8898 0.4732 0.122 Uiso 1 1 calc R . .
H20B H 0.5162 0.8355 0.5517 0.122 Uiso 1 1 calc R . .
H20C H 0.5501 0.7760 0.4799 0.122 Uiso 1 1 calc R . .
C21 C 0.6860(5) 0.9678(4) 0.5922(4) 0.0693(16) Uani 1 1 d . . .
H21A H 0.7616 0.9809 0.6231 0.104 Uiso 1 1 calc R . .
H21B H 0.6377 0.9696 0.6285 0.104 Uiso 1 1 calc R . .
H21C H 0.6650 1.0178 0.5529 0.104 Uiso 1 1 calc R . .
C22 C 1.0375(4) 0.7872(3) 0.4830(3) 0.0416(11) Uani 1 1 d . . .
H22 H 1.0476 0.7563 0.5355 0.050 Uiso 1 1 calc R . .
C23 C 1.0546(4) 0.7080(4) 0.4217(3) 0.0602(14) Uani 1 1 d . . .
H23A H 0.9969 0.6569 0.4137 0.090 Uiso 1 1 calc R . .
H23B H 1.1258 0.6792 0.4416 0.090 Uiso 1 1 calc R . .
H23C H 1.0520 0.7374 0.3707 0.090 Uiso 1 1 calc R . .
C24 C 1.1242(5) 0.8688(4) 0.4941(4) 0.0676(16) Uani 1 1 d . . .
H24A H 1.1967 0.8412 0.5101 0.101 Uiso 1 1 calc R . .
H24B H 1.1153 0.9170 0.5358 0.101 Uiso 1 1 calc R . .
H24C H 1.1165 0.9008 0.4435 0.101 Uiso 1 1 calc R . .
C25 C 0.9698(3) 0.8535(3) 0.6446(2) 0.0251(8) Uani 1 1 d . . .
H25 H 0.9885 0.9165 0.6300 0.030 Uiso 1 1 calc R . .
C26 C 0.7252(3) 0.5497(3) 0.7664(2) 0.0268(9) Uani 1 1 d . . .
C27 C 0.6709(3) 0.6235(3) 0.8002(2) 0.0328(10) Uani 1 1 d . . .
C28 C 0.5645(3) 0.6037(3) 0.8045(3) 0.0413(11) Uani 1 1 d . . .
H28 H 0.5267 0.6527 0.8266 0.050 Uiso 1 1 calc R . .
C29 C 0.5130(3) 0.5145(4) 0.7773(3) 0.0502(13) Uani 1 1 d . . .
H29 H 0.4408 0.5019 0.7818 0.060 Uiso 1 1 calc R . .
C30 C 0.5658(3) 0.4430(3) 0.7433(3) 0.0460(12) Uani 1 1 d . . .
H30 H 0.5291 0.3819 0.7238 0.055 Uiso 1 1 calc R . .
C31 C 0.6723(3) 0.4595(3) 0.7373(2) 0.0340(10) Uani 1 1 d . . .
C32 C 0.7241(3) 0.7238(3) 0.8268(3) 0.0371(10) Uani 1 1 d . . .
H32 H 0.8048 0.7156 0.8420 0.045 Uiso 1 1 calc R . .
C33 C 0.6989(4) 0.7887(4) 0.7564(3) 0.0554(13) Uani 1 1 d . . .
H33A H 0.7289 0.7606 0.7135 0.083 Uiso 1 1 calc R . .
H33B H 0.7317 0.8543 0.7735 0.083 Uiso 1 1 calc R . .
H33C H 0.6196 0.7932 0.7367 0.083 Uiso 1 1 calc R . .
C34 C 0.6930(4) 0.7711(4) 0.9002(3) 0.0606(14) Uani 1 1 d . . .
H34A H 0.6155 0.7864 0.8857 0.091 Uiso 1 1 calc R . .
H34B H 0.7371 0.8315 0.9185 0.091 Uiso 1 1 calc R . .
H34C H 0.7065 0.7254 0.9434 0.091 Uiso 1 1 calc R . .
C35 C 0.7327(3) 0.3797(3) 0.7022(3) 0.0414(11) Uani 1 1 d . . .
H35 H 0.7870 0.4130 0.6783 0.050 Uiso 1 1 calc R . .
C36 C 0.6570(4) 0.3133(4) 0.6353(3) 0.0662(16) Uani 1 1 d . . .
H36A H 0.7010 0.2689 0.6110 0.099 Uiso 1 1 calc R . .
H36B H 0.6145 0.3539 0.5943 0.099 Uiso 1 1 calc R . .
H36C H 0.6073 0.2747 0.6581 0.099 Uiso 1 1 calc R . .
C37 C 0.7955(4) 0.3177(3) 0.7675(3) 0.0556(14) Uani 1 1 d . . .
H37A H 0.8460 0.3599 0.8085 0.083 Uiso 1 1 calc R . .
H37B H 0.8367 0.2695 0.7442 0.083 Uiso 1 1 calc R . .
H37C H 0.7443 0.2835 0.7919 0.083 Uiso 1 1 calc R . .
C38 C 1.1053(3) 0.5497(3) 0.8779(2) 0.0234(8) Uani 1 1 d . . .
C39 C 1.1630(3) 0.4631(3) 0.8733(2) 0.0288(9) Uani 1 1 d . . .
C40 C 1.2507(4) 0.4456(3) 0.9371(3) 0.0468(12) Uani 1 1 d . . .
H40 H 1.2905 0.3878 0.9349 0.056 Uiso 1 1 calc R . .
C41 C 1.2815(4) 0.5095(3) 1.0034(3) 0.0477(12) Uani 1 1 d . . .
H41 H 1.3408 0.4950 1.0468 0.057 Uiso 1 1 calc R . .
C42 C 1.2265(4) 0.5944(3) 1.0071(2) 0.0422(11) Uani 1 1 d . . .
H42 H 1.2488 0.6388 1.0528 0.051 Uiso 1 1 calc R . .
C43 C 1.1380(3) 0.6164(3) 0.9443(2) 0.0295(9) Uani 1 1 d . . .
C44 C 1.1323(3) 0.3906(3) 0.8002(3) 0.0360(10) Uani 1 1 d . . .
H44 H 1.0563 0.4041 0.7698 0.043 Uiso 1 1 calc R . .
C45 C 1.2056(4) 0.4049(4) 0.7456(3) 0.0539(13) Uani 1 1 d . . .
H45A H 1.1992 0.4716 0.7270 0.081 Uiso 1 1 calc R . .
H45B H 1.1842 0.3576 0.6993 0.081 Uiso 1 1 calc R . .
H45C H 1.2812 0.3948 0.7745 0.081 Uiso 1 1 calc R . .
C46 C 1.1333(4) 0.2852(3) 0.8233(3) 0.0557(13) Uani 1 1 d . . .
H46A H 1.1021 0.2422 0.7755 0.084 Uiso 1 1 calc R . .
H46B H 1.0898 0.2778 0.8624 0.084 Uiso 1 1 calc R . .
H46C H 1.2085 0.2672 0.8470 0.084 Uiso 1 1 calc R . .
C47 C 1.0791(3) 0.7124(3) 0.9501(2) 0.0356(10) Uani 1 1 d . . .
H47 H 1.0357 0.7254 0.8949 0.043 Uiso 1 1 calc R . .
C48 C 1.1589(4) 0.7996(3) 0.9802(3) 0.0484(12) Uani 1 1 d . . .
H48A H 1.1987 0.7913 1.0359 0.073 Uiso 1 1 calc R . .
H48B H 1.1185 0.8602 0.9774 0.073 Uiso 1 1 calc R . .
H48C H 1.2108 0.8032 0.9467 0.073 Uiso 1 1 calc R . .
C49 C 0.9995(4) 0.7022(4) 1.0025(3) 0.0541(13) Uani 1 1 d . . .
H49A H 0.9482 0.6469 0.9812 0.081 Uiso 1 1 calc R . .
H49B H 0.9592 0.7626 1.0026 0.081 Uiso 1 1 calc R . .
H49C H 1.0400 0.6906 1.0574 0.081 Uiso 1 1 calc R . .
C50 C 0.9167(3) 0.5519(3) 0.8180(2) 0.0226(8) Uani 1 1 d . . .
H50 H 0.9050 0.5253 0.8650 0.027 Uiso 1 1 calc R . .
C51 C 0.6838(4) 0.5767(4) 0.5489(3) 0.0513(13) Uani 1 1 d . . .
H51A H 0.6617 0.6457 0.5448 0.062 Uiso 1 1 calc R A 1
H51B H 0.6603 0.5492 0.5941 0.062 Uiso 1 1 calc R A 1
C52A C 0.6308(18) 0.515(2) 0.4680(17) 0.096(9) Uani 0.62(4) 1 d P B 1
H52A H 0.5856 0.4589 0.4773 0.115 Uiso 0.62(4) 1 calc PR B 1
H52B H 0.5852 0.5561 0.4280 0.115 Uiso 0.62(4) 1 calc PR B 1
C52B C 0.644(2) 0.554(3) 0.464(2) 0.060(9) Uani 0.38(4) 1 d P B 2
H52C H 0.5892 0.4993 0.4556 0.072 Uiso 0.38(4) 1 calc PR B 2
H52D H 0.6051 0.6118 0.4395 0.072 Uiso 0.38(4) 1 calc PR B 2
C53A C 0.7234(13) 0.4820(9) 0.4425(10) 0.046(4) Uani 0.62(4) 1 d P B 1
H53A H 0.7104 0.4876 0.3840 0.055 Uiso 0.62(4) 1 calc PR B 1
H53B H 0.7345 0.4121 0.4539 0.055 Uiso 0.62(4) 1 calc PR B 1
C53B C 0.714(3) 0.531(6) 0.4246(17) 0.14(2) Uani 0.38(4) 1 d P B 2
H53C H 0.7108 0.5757 0.3808 0.165 Uiso 0.38(4) 1 calc PR B 2
H53D H 0.6998 0.4630 0.4013 0.165 Uiso 0.38(4) 1 calc PR B 2
C54 C 0.8226(4) 0.5412(4) 0.4847(3) 0.0600(15) Uani 1 1 d . . .
H54A H 0.8885 0.5015 0.4926 0.072 Uiso 1 1 calc R B 1
H54B H 0.8326 0.5989 0.4545 0.072 Uiso 1 1 calc R B 1
C55 C 1.416(3) 0.944(3) 1.085(2) 0.129(11) Uani 0.558(19) 1 d P C 1
C56 C 1.415(2) 0.969(2) 1.161(2) 0.132(14) Uani 0.558(19) 1 d P C 1
C57 C 1.4675(16) 0.9126(19) 1.2251(10) 0.079(6) Uani 0.558(19) 1 d P C 1
C58 C 1.5176(14) 0.8245(14) 1.2211(11) 0.100(6) Uani 0.558(19) 1 d P C 1
C59 C 1.5041(7) 0.7855(8) 1.1563(7) 0.116(3) Uani 1 1 d . . .
C60 C 1.506(2) 0.730(2) 1.068(4) 0.26(3) Uani 0.442(19) 1 d P C 2
C61 C 1.4718(16) 0.757(3) 1.0122(12) 0.251(15) Uani 1 1 d . . .
C62 C 1.449(3) 0.865(4) 1.026(4) 0.19(3) Uani 0.442(19) 1 d P C 2
C63 C 1.433(2) 0.8984(16) 1.0661(16) 0.057(7) Uani 0.442(19) 1 d P C 2
C64 C 1.4690(7) 0.8146(8) 1.0811(6) 0.047(4) Uani 0.558(19) 1 d P C 1
C65 C 1.459(3) 0.893(3) 1.163(5) 0.18(2) Uani 0.442(19) 1 d P C 2
C66 C 1.434(3) 0.952(3) 1.206(4) 0.18(3) Uani 0.442(19) 1 d P C 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
La1 0.02493(12) 0.02226(12) 0.01783(11) 0.00277(8) 0.00574(8) 0.00360(8)
F1 0.0437(14) 0.0578(16) 0.0372(14) -0.0064(12) 0.0192(12) 0.0162(12)
O1 0.0351(16) 0.0430(17) 0.0244(15) -0.0074(13) 0.0054(12) -0.0023(12)
N1 0.0212(16) 0.0252(17) 0.0206(16) 0.0047(13) 0.0024(13) 0.0031(12)
N2 0.0289(17) 0.0268(18) 0.0176(16) 0.0025(13) -0.0018(14) 0.0008(13)
N3 0.0178(16) 0.0362(19) 0.0268(17) 0.0074(15) 0.0052(14) 0.0031(13)
N4 0.0152(15) 0.0321(18) 0.0227(16) 0.0031(14) 0.0007(13) 0.0016(12)
C1 0.026(2) 0.024(2) 0.0187(19) 0.0046(16) -0.0004(16) -0.0017(15)
C2 0.028(2) 0.032(2) 0.027(2) 0.0083(17) 0.0007(17) -0.0027(16)
C3 0.025(2) 0.041(3) 0.039(2) 0.012(2) -0.0014(19) -0.0054(18)
C4 0.039(3) 0.033(2) 0.039(3) -0.001(2) -0.009(2) -0.0077(19)
C5 0.042(3) 0.028(2) 0.035(2) -0.0024(19) -0.002(2) -0.0002(18)
C6 0.034(2) 0.027(2) 0.022(2) 0.0026(17) 0.0028(17) -0.0011(16)
C7 0.028(2) 0.043(3) 0.035(2) 0.004(2) 0.0074(18) 0.0035(18)
C8 0.060(3) 0.040(3) 0.058(3) -0.001(2) 0.023(3) 0.012(2)
C9 0.053(3) 0.068(4) 0.074(4) 0.005(3) 0.035(3) 0.001(3)
C10 0.031(2) 0.028(2) 0.035(2) -0.0046(18) 0.0049(18) 0.0031(17)
C11 0.052(3) 0.077(4) 0.044(3) -0.002(3) 0.019(2) 0.011(3)
C12 0.042(3) 0.052(3) 0.087(4) 0.022(3) 0.008(3) 0.010(2)
C13 0.039(2) 0.022(2) 0.022(2) 0.0028(16) -0.0053(18) -0.0038(17)
C14 0.042(3) 0.032(2) 0.034(2) 0.0061(19) -0.010(2) 0.0059(19)
C15 0.072(4) 0.045(3) 0.037(3) 0.010(2) -0.012(3) 0.017(3)
C16 0.100(5) 0.049(3) 0.027(3) 0.009(2) -0.015(3) 0.011(3)
C17 0.090(4) 0.042(3) 0.024(2) 0.002(2) 0.008(3) 0.003(3)
C18 0.053(3) 0.031(2) 0.023(2) 0.0057(18) 0.003(2) -0.0033(19)
C19 0.033(2) 0.051(3) 0.054(3) 0.019(2) -0.007(2) 0.008(2)
C20 0.036(3) 0.091(5) 0.102(5) 0.024(4) -0.014(3) 0.002(3)
C21 0.062(4) 0.075(4) 0.075(4) -0.001(3) 0.026(3) 0.006(3)
C22 0.058(3) 0.042(3) 0.029(2) 0.005(2) 0.017(2) 0.000(2)
C23 0.071(4) 0.061(3) 0.055(3) -0.002(3) 0.030(3) 0.002(3)
C24 0.070(4) 0.070(4) 0.062(4) -0.003(3) 0.019(3) -0.020(3)
C25 0.029(2) 0.025(2) 0.023(2) 0.0037(16) 0.0085(17) 0.0031(16)
C26 0.0204(19) 0.039(2) 0.0208(19) 0.0132(17) 0.0030(16) -0.0007(16)
C27 0.022(2) 0.047(3) 0.031(2) 0.0129(19) 0.0069(17) 0.0074(17)
C28 0.029(2) 0.049(3) 0.051(3) 0.013(2) 0.016(2) 0.008(2)
C29 0.019(2) 0.064(3) 0.069(4) 0.020(3) 0.013(2) 0.000(2)
C30 0.030(2) 0.046(3) 0.058(3) 0.012(2) 0.002(2) -0.007(2)
C31 0.024(2) 0.041(3) 0.035(2) 0.0098(19) 0.0023(18) -0.0008(17)
C32 0.033(2) 0.042(3) 0.039(3) 0.002(2) 0.016(2) 0.0049(19)
C33 0.060(3) 0.050(3) 0.057(3) 0.011(3) 0.015(3) -0.009(2)
C34 0.074(4) 0.058(3) 0.060(3) -0.004(3) 0.036(3) 0.003(3)
C35 0.036(2) 0.042(3) 0.043(3) 0.000(2) 0.004(2) -0.0023(19)
C36 0.060(3) 0.062(4) 0.066(4) -0.012(3) 0.000(3) -0.013(3)
C37 0.054(3) 0.044(3) 0.063(3) 0.001(3) 0.005(3) 0.013(2)
C38 0.0217(19) 0.031(2) 0.0167(18) 0.0093(16) 0.0014(15) 0.0030(15)
C39 0.022(2) 0.029(2) 0.034(2) 0.0066(18) 0.0027(17) 0.0012(16)
C40 0.038(3) 0.042(3) 0.053(3) 0.013(2) -0.005(2) 0.012(2)
C41 0.039(3) 0.055(3) 0.035(3) 0.011(2) -0.019(2) 0.008(2)
C42 0.047(3) 0.049(3) 0.023(2) 0.003(2) -0.007(2) 0.003(2)
C43 0.027(2) 0.036(2) 0.025(2) 0.0072(18) 0.0050(17) 0.0038(17)
C44 0.028(2) 0.037(2) 0.041(3) 0.000(2) 0.0057(19) 0.0053(17)
C45 0.075(4) 0.047(3) 0.041(3) 0.004(2) 0.018(3) -0.008(2)
C46 0.083(4) 0.040(3) 0.055(3) -0.001(2) 0.039(3) -0.009(2)
C47 0.038(2) 0.046(3) 0.023(2) 0.0009(19) 0.0064(18) 0.0062(19)
C48 0.056(3) 0.044(3) 0.042(3) -0.002(2) 0.006(2) 0.004(2)
C49 0.057(3) 0.068(4) 0.041(3) 0.000(3) 0.018(2) 0.015(3)
C50 0.023(2) 0.029(2) 0.0166(18) 0.0014(16) 0.0053(15) 0.0028(15)
C51 0.041(3) 0.077(4) 0.034(3) -0.005(2) 0.006(2) 0.019(2)
C52A 0.062(10) 0.17(2) 0.049(8) -0.039(13) 0.013(6) -0.054(11)
C52B 0.015(10) 0.10(2) 0.045(12) -0.031(14) -0.016(9) 0.002(12)
C53A 0.045(6) 0.061(7) 0.031(8) -0.021(5) 0.014(5) -0.005(5)
C53B 0.062(17) 0.32(6) 0.021(10) -0.01(2) 0.007(10) -0.06(3)
C54 0.050(3) 0.099(4) 0.029(3) -0.024(3) 0.014(2) -0.021(3)
C55 0.093(19) 0.19(3) 0.084(16) 0.02(2) -0.019(14) -0.056(19)
C56 0.044(10) 0.079(18) 0.23(3) 0.043(16) -0.047(15) -0.021(12)
C57 0.054(10) 0.097(16) 0.083(11) -0.025(9) 0.019(7) 0.014(8)
C58 0.101(12) 0.105(14) 0.090(11) -0.008(10) 0.024(10) -0.043(10)
C59 0.090(6) 0.111(8) 0.133(8) 0.070(7) -0.011(6) -0.019(5)
C60 0.071(16) 0.105(19) 0.62(9) -0.17(4) 0.15(3) -0.046(13)
C61 0.128(15) 0.50(4) 0.147(13) -0.041(19) 0.089(11) -0.045(18)
C62 0.08(2) 0.24(5) 0.21(5) 0.09(4) -0.07(3) -0.09(3)
C63 0.054(10) 0.042(11) 0.068(18) 0.024(10) -0.006(11) 0.016(9)
C64 0.017(4) 0.081(9) 0.047(7) 0.011(6) 0.015(4) 0.001(4)
C65 0.058(17) 0.15(4) 0.36(8) -0.04(5) 0.10(3) -0.05(2)
C66 0.07(2) 0.068(18) 0.44(9) -0.02(3) 0.12(4) 0.032(13)

_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
La1 F1 2.136(2) . ?
La1 N1 2.538(3) . ?
La1 O1 2.539(3) . ?
La1 N3 2.543(3) . ?
La1 N4 2.560(3) . ?
La1 N2 2.578(3) . ?
La1 C25 2.928(4) . ?
La1 C50 2.947(4) . ?
O1 C51 1.441(5) . ?
O1 C54 1.461(5) . ?
N1 C25 1.319(4) . ?
N1 C1 1.437(4) . ?
N2 C25 1.316(5) . ?
N2 C13 1.430(5) . ?
N3 C50 1.322(4) . ?
N3 C26 1.432(5) . ?
N4 C50 1.316(4) . ?
N4 C38 1.431(4) . ?
C1 C6 1.400(5) . ?
C1 C2 1.408(5) . ?
C2 C3 1.401(5) . ?
C2 C7 1.519(5) . ?
C3 C4 1.377(6) . ?
C4 C5 1.375(6) . ?
C5 C6 1.396(5) . ?
C6 C10 1.521(5) . ?
C7 C9 1.512(6) . ?
C7 C8 1.525(6) . ?
C10 C12 1.511(6) . ?
C10 C11 1.518(6) . ?
C13 C18 1.406(6) . ?
C13 C14 1.413(5) . ?
C14 C15 1.392(6) . ?
C14 C19 1.509(7) . ?
C15 C16 1.369(8) . ?
C16 C17 1.383(7) . ?
C17 C18 1.399(6) . ?
C18 C22 1.528(6) . ?
C19 C21 1.526(7) . ?
C19 C20 1.535(7) . ?
C22 C24 1.520(7) . ?
C22 C23 1.531(6) . ?
C26 C31 1.398(6) . ?
C26 C27 1.414(5) . ?
C27 C28 1.391(6) . ?
C27 C32 1.513(6) . ?
C28 C29 1.374(6) . ?
C29 C30 1.384(7) . ?
C30 C31 1.395(6) . ?
C31 C35 1.531(6) . ?
C32 C33 1.513(6) . ?
C32 C34 1.536(6) . ?
C35 C37 1.514(6) . ?
C35 C36 1.543(6) . ?
C38 C43 1.399(5) . ?
C38 C39 1.414(5) . ?
C39 C40 1.389(5) . ?
C39 C44 1.528(6) . ?
C40 C41 1.374(6) . ?
C41 C42 1.372(6) . ?
C42 C43 1.400(5) . ?
C43 C47 1.534(5) . ?
C44 C45 1.498(6) . ?
C44 C46 1.514(6) . ?
C47 C49 1.524(6) . ?
C47 C48 1.529(6) . ?
C51 C52B 1.45(4) . ?
C51 C52A 1.58(3) . ?
C52A C53A 1.43(3) . ?
C52B C53B 1.27(6) . ?
C53A C54 1.484(16) . ?
C53B C54 1.50(3) . ?
C55 C56 1.34(5) . ?
C55 C64 1.91(5) . ?
C56 C57 1.42(4) . ?
C57 C58 1.38(3) . ?
C58 C59 1.186(17) . ?
C59 C64 1.347(14) . ?
C59 C65 1.59(4) . ?
C59 C60 1.68(5) . ?
C60 C61 1.04(7) . ?
C61 C64 1.40(2) . ?
C61 C62 1.53(5) . ?
C62 C63 0.88(7) . ?
C63 C65 1.63(9) . ?
C65 C66 1.17(6) . ?

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
F1 La1 N1 109.22(10) . . ?
F1 La1 O1 85.12(9) . . ?
N1 La1 O1 132.05(9) . . ?
F1 La1 N3 127.61(10) . . ?
N1 La1 N3 117.24(10) . . ?
O1 La1 N3 81.45(9) . . ?
F1 La1 N4 97.69(9) . . ?
N1 La1 N4 99.72(9) . . ?
O1 La1 N4 124.14(9) . . ?
N3 La1 N4 53.04(9) . . ?
F1 La1 N2 103.96(10) . . ?
N1 La1 N2 53.02(9) . . ?
O1 La1 N2 79.36(9) . . ?
N3 La1 N2 122.54(9) . . ?
N4 La1 N2 149.54(10) . . ?
F1 La1 C25 105.14(10) . . ?
N1 La1 C25 26.73(9) . . ?
O1 La1 C25 106.05(9) . . ?
N3 La1 C25 127.25(10) . . ?
N4 La1 C25 126.19(10) . . ?
N2 La1 C25 26.70(9) . . ?
F1 La1 C50 115.35(10) . . ?
N1 La1 C50 109.54(10) . . ?
O1 La1 C50 103.95(9) . . ?
N3 La1 C50 26.59(9) . . ?
N4 La1 C50 26.48(9) . . ?
N2 La1 C50 140.68(9) . . ?
C25 La1 C50 130.93(10) . . ?
C51 O1 C54 108.1(3) . . ?
C51 O1 La1 128.8(2) . . ?
C54 O1 La1 120.6(2) . . ?
C25 N1 C1 116.6(3) . . ?
C25 N1 La1 93.4(2) . . ?
C1 N1 La1 147.8(2) . . ?
C25 N2 C13 117.6(3) . . ?
C25 N2 La1 91.6(2) . . ?
C13 N2 La1 143.4(2) . . ?
C50 N3 C26 118.2(3) . . ?
C50 N3 La1 94.0(2) . . ?
C26 N3 La1 147.4(2) . . ?
C50 N4 C38 118.0(3) . . ?
C50 N4 La1 93.4(2) . . ?
C38 N4 La1 148.5(2) . . ?
C6 C1 C2 120.8(3) . . ?
C6 C1 N1 120.3(3) . . ?
C2 C1 N1 118.9(3) . . ?
C3 C2 C1 118.1(4) . . ?
C3 C2 C7 120.6(4) . . ?
C1 C2 C7 121.3(3) . . ?
C4 C3 C2 121.2(4) . . ?
C5 C4 C3 120.0(4) . . ?
C4 C5 C6 121.2(4) . . ?
C5 C6 C1 118.7(4) . . ?
C5 C6 C10 119.7(3) . . ?
C1 C6 C10 121.7(3) . . ?
C9 C7 C2 114.6(4) . . ?
C9 C7 C8 111.2(4) . . ?
C2 C7 C8 109.5(3) . . ?
C12 C10 C11 109.0(4) . . ?
C12 C10 C6 112.3(4) . . ?
C11 C10 C6 112.0(3) . . ?
C18 C13 C14 120.4(4) . . ?
C18 C13 N2 120.5(3) . . ?
C14 C13 N2 119.1(4) . . ?
C15 C14 C13 118.3(5) . . ?
C15 C14 C19 121.4(4) . . ?
C13 C14 C19 120.3(4) . . ?
C16 C15 C14 121.5(5) . . ?
C15 C16 C17 120.6(4) . . ?
C16 C17 C18 120.3(5) . . ?
C17 C18 C13 118.9(4) . . ?
C17 C18 C22 118.4(4) . . ?
C13 C18 C22 122.7(3) . . ?
C14 C19 C21 110.8(4) . . ?
C14 C19 C20 113.9(4) . . ?
C21 C19 C20 109.8(4) . . ?
C24 C22 C18 112.0(4) . . ?
C24 C22 C23 110.1(4) . . ?
C18 C22 C23 112.3(4) . . ?
N2 C25 N1 120.1(3) . . ?
N2 C25 La1 61.66(19) . . ?
N1 C25 La1 59.90(19) . . ?
C31 C26 C27 120.6(4) . . ?
C31 C26 N3 119.8(3) . . ?
C27 C26 N3 119.5(3) . . ?
C28 C27 C26 118.4(4) . . ?
C28 C27 C32 120.3(4) . . ?
C26 C27 C32 121.2(3) . . ?
C29 C28 C27 121.2(4) . . ?
C28 C29 C30 120.2(4) . . ?
C29 C30 C31 120.7(4) . . ?
C30 C31 C26 118.9(4) . . ?
C30 C31 C35 121.1(4) . . ?
C26 C31 C35 120.0(4) . . ?
C27 C32 C33 109.0(4) . . ?
C27 C32 C34 113.6(4) . . ?
C33 C32 C34 111.9(4) . . ?
C37 C35 C31 110.8(4) . . ?
C37 C35 C36 109.8(4) . . ?
C31 C35 C36 113.3(4) . . ?
C43 C38 C39 120.4(3) . . ?
C43 C38 N4 120.2(3) . . ?
C39 C38 N4 119.3(3) . . ?
C40 C39 C38 118.1(4) . . ?
C40 C39 C44 120.1(3) . . ?
C38 C39 C44 121.8(3) . . ?
C41 C40 C39 121.8(4) . . ?
C42 C41 C40 120.0(4) . . ?
C41 C42 C43 120.8(4) . . ?
C38 C43 C42 118.9(4) . . ?
C38 C43 C47 121.7(3) . . ?
C42 C43 C47 119.4(4) . . ?
C45 C44 C46 110.1(4) . . ?
C45 C44 C39 111.1(4) . . ?
C46 C44 C39 112.3(4) . . ?
C49 C47 C48 111.0(4) . . ?
C49 C47 C43 110.6(4) . . ?
C48 C47 C43 112.1(3) . . ?
N4 C50 N3 119.4(3) . . ?
N4 C50 La1 60.13(19) . . ?
N3 C50 La1 59.4(2) . . ?
O1 C51 C52B 102.7(12) . . ?
O1 C51 C52A 106.3(9) . . ?
C52B C51 C52A 21(2) . . ?
C53A C52A C51 103.0(15) . . ?
C53B C52B C51 117(2) . . ?
C52A C53A C54 110.5(14) . . ?
C52B C53B C54 106(2) . . ?
O1 C54 C53A 103.2(7) . . ?
O1 C54 C53B 106.1(14) . . ?
C53A C54 C53B 29(3) . . ?
C56 C55 C64 108(3) . . ?
C55 C56 C57 121(4) . . ?
C58 C57 C56 128(3) . . ?
C59 C58 C57 116.1(18) . . ?
C58 C59 C64 134.6(15) . . ?
C58 C59 C65 62(3) . . ?
C64 C59 C65 73(3) . . ?
C58 C59 C60 171.0(16) . . ?
C64 C59 C60 48.8(18) . . ?
C65 C59 C60 122(3) . . ?
C61 C60 C59 125(3) . . ?
C60 C61 C64 61(2) . . ?
C60 C61 C62 107(3) . . ?
C64 C61 C62 47(2) . . ?
C63 C62 C61 133(6) . . ?
C62 C63 C65 137(4) . . ?
C59 C64 C61 124.0(18) . . ?
C59 C64 C55 109.1(14) . . ?
C61 C64 C55 126.9(18) . . ?
C66 C65 C59 145(9) . . ?
C66 C65 C63 124(7) . . ?
C59 C65 C63 90(3) . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        27.85
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         1.328
_refine_diff_density_min         -1.203
_refine_diff_density_rms         0.125

data_compound_2
_database_code_depnum_ccdc_archive 'CCDC 253457'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_ccdc_chemical_compound_source_recrystallisation Toluene
_chemical_name_common            (DippForm(CH2)4O(o-HC6F4))
_chemical_melting_point          433
_chemical_formula_moiety         'C35 H44 F4 N2 O'
_chemical_formula_sum            'C35 H44 F4 N2 O'
_chemical_formula_weight         584.72

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   P21/n
_symmetry_Int_Tables_number      14

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

_cell_length_a                   10.6132(3)
_cell_length_b                   20.4222(7)
_cell_length_c                   14.8655(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.5310(10)
_cell_angle_gamma                90.00
_cell_volume                     3186.37(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1248
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9738
_exptl_absorpt_correction_T_max  0.9912
_exptl_absorpt_process_details   'performed as part of the DENZO-SMN program'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'psi 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            25587
_diffrn_reflns_av_R_equivalents  0.1111
_diffrn_reflns_av_sigmaI/netI    0.1313
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.72
_diffrn_reflns_theta_max         28.13
_reflns_number_total             7680
_reflns_number_gt                3758
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Nonius Collect'
_computing_cell_refinement       DENZO-SMN
_computing_data_reduction        X-Seed
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-Seed / POV-Ray'
_computing_publication_material  'Microsoft Office 2000'

_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^)+(0.0601P)^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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7680
_refine_ls_number_parameters     387
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1531
_refine_ls_R_factor_gt           0.0568
_refine_ls_wR_factor_ref         0.1381
_refine_ls_wR_factor_gt          0.1118
_refine_ls_goodness_of_fit_ref   0.938
_refine_ls_restrained_S_all      0.938
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.45821(13) 0.15992(6) 0.09181(9) 0.0469(4) Uani 1 1 d . . .
F2 F 0.68691(13) 0.10424(8) 0.08252(10) 0.0582(4) Uani 1 1 d . . .
F3 F 0.71807(13) -0.02723(7) 0.09941(9) 0.0567(4) Uani 1 1 d . . .
F4 F 0.51785(14) -0.10327(6) 0.12928(9) 0.0501(4) Uani 1 1 d . . .
O1 O 0.25598(13) 0.08871(6) 0.11447(9) 0.0306(4) Uani 1 1 d . . .
N1 N -0.07185(15) 0.19666(7) -0.13958(10) 0.0198(4) Uani 1 1 d . . .
N2 N -0.14516(15) 0.10386(7) -0.22106(10) 0.0206(4) Uani 1 1 d . . .
C1 C -0.04774(19) 0.26591(8) -0.14334(12) 0.0204(4) Uani 1 1 d . . .
C2 C -0.14750(19) 0.30923(9) -0.13242(13) 0.0242(5) Uani 1 1 d . . .
C3 C -0.1246(2) 0.37617(9) -0.13805(13) 0.0301(5) Uani 1 1 d . . .
H3 H -0.1904 0.4064 -0.1309 0.036 Uiso 1 1 calc R . .
C4 C -0.0077(2) 0.39906(10) -0.15378(13) 0.0318(5) Uani 1 1 d . . .
H4 H 0.0062 0.4449 -0.1579 0.038 Uiso 1 1 calc R . .
C5 C 0.0894(2) 0.35588(9) -0.16358(13) 0.0290(5) Uani 1 1 d . . .
H5 H 0.1697 0.3724 -0.1739 0.035 Uiso 1 1 calc R . .
C6 C 0.07186(19) 0.28836(9) -0.15853(13) 0.0232(5) Uani 1 1 d . . .
C7 C -0.2779(2) 0.28548(10) -0.11744(14) 0.0295(5) Uani 1 1 d . . .
H7 H -0.2785 0.2366 -0.1220 0.035 Uiso 1 1 calc R . .
C8 C -0.3078(2) 0.30389(12) -0.02261(16) 0.0454(6) Uani 1 1 d . . .
H8A H -0.2426 0.2853 0.0240 0.068 Uiso 1 1 calc R . .
H8B H -0.3915 0.2864 -0.0148 0.068 Uiso 1 1 calc R . .
H8C H -0.3084 0.3517 -0.0165 0.068 Uiso 1 1 calc R . .
C9 C -0.3808(2) 0.31175(11) -0.19117(17) 0.0472(7) Uani 1 1 d . . .
H9A H -0.3851 0.3595 -0.1863 0.071 Uiso 1 1 calc R . .
H9B H -0.4633 0.2927 -0.1834 0.071 Uiso 1 1 calc R . .
H9C H -0.3601 0.2999 -0.2512 0.071 Uiso 1 1 calc R . .
C10 C 0.1824(2) 0.24324(10) -0.16920(14) 0.0298(5) Uani 1 1 d . . .
H10 H 0.1513 0.1971 -0.1676 0.036 Uiso 1 1 calc R . .
C11 C 0.2922(2) 0.25167(11) -0.09108(16) 0.0419(6) Uani 1 1 d . . .
H11A H 0.3235 0.2968 -0.0904 0.063 Uiso 1 1 calc R . .
H11B H 0.3614 0.2215 -0.0995 0.063 Uiso 1 1 calc R . .
H11C H 0.2622 0.2421 -0.0333 0.063 Uiso 1 1 calc R . .
C12 C 0.2287(2) 0.25399(11) -0.26132(15) 0.0435(6) Uani 1 1 d . . .
H12A H 0.1569 0.2488 -0.3105 0.065 Uiso 1 1 calc R . .
H12B H 0.2947 0.2218 -0.2688 0.065 Uiso 1 1 calc R . .
H12C H 0.2638 0.2982 -0.2634 0.065 Uiso 1 1 calc R . .
C13 C -0.17676(19) 0.07429(8) -0.30852(12) 0.0200(4) Uani 1 1 d . . .
C14 C -0.08582(18) 0.03166(8) -0.33804(13) 0.0208(4) Uani 1 1 d . . .
C15 C -0.1187(2) -0.00075(9) -0.42090(13) 0.0247(5) Uani 1 1 d . . .
H15 H -0.0591 -0.0297 -0.4417 0.030 Uiso 1 1 calc R . .
C16 C -0.2362(2) 0.00849(9) -0.47321(13) 0.0266(5) Uani 1 1 d . . .
H16 H -0.2567 -0.0138 -0.5296 0.032 Uiso 1 1 calc R . .
C17 C -0.3234(2) 0.04991(9) -0.44365(13) 0.0263(5) Uani 1 1 d . . .
H17 H -0.4041 0.0557 -0.4800 0.032 Uiso 1 1 calc R . .
C18 C -0.29626(19) 0.08393(8) -0.36108(12) 0.0210(4) Uani 1 1 d . . .
C19 C 0.04657(19) 0.02627(9) -0.28407(13) 0.0248(5) Uani 1 1 d . . .
H19 H 0.0385 0.0328 -0.2185 0.030 Uiso 1 1 calc R . .
C20 C 0.1115(2) -0.03977(9) -0.29224(15) 0.0320(5) Uani 1 1 d . . .
H20A H 0.0586 -0.0747 -0.2724 0.048 Uiso 1 1 calc R . .
H20B H 0.1950 -0.0398 -0.2538 0.048 Uiso 1 1 calc R . .
H20C H 0.1227 -0.0472 -0.3557 0.048 Uiso 1 1 calc R . .
C21 C 0.1301(2) 0.08159(10) -0.31157(15) 0.0328(5) Uani 1 1 d . . .
H21A H 0.1404 0.0764 -0.3756 0.049 Uiso 1 1 calc R . .
H21B H 0.2139 0.0800 -0.2736 0.049 Uiso 1 1 calc R . .
H21C H 0.0896 0.1238 -0.3031 0.049 Uiso 1 1 calc R . .
C22 C -0.3944(2) 0.13116(9) -0.33391(13) 0.0254(5) Uani 1 1 d . . .
H22 H -0.3698 0.1420 -0.2680 0.031 Uiso 1 1 calc R . .
C23 C -0.5293(2) 0.10277(10) -0.34685(15) 0.0330(5) Uani 1 1 d . . .
H23A H -0.5594 0.0968 -0.4119 0.050 Uiso 1 1 calc R . .
H23B H -0.5863 0.1329 -0.3211 0.050 Uiso 1 1 calc R . .
H23C H -0.5286 0.0604 -0.3158 0.050 Uiso 1 1 calc R . .
C24 C -0.3943(2) 0.19507(9) -0.38877(15) 0.0371(6) Uani 1 1 d . . .
H24A H -0.3107 0.2161 -0.3750 0.056 Uiso 1 1 calc R . .
H24B H -0.4600 0.2246 -0.3723 0.056 Uiso 1 1 calc R . .
H24C H -0.4121 0.1852 -0.4539 0.056 Uiso 1 1 calc R . .
C25 C -0.10845(18) 0.16349(9) -0.21825(12) 0.0196(4) Uani 1 1 d . . .
H25 H -0.1067 0.1858 -0.2741 0.023 Uiso 1 1 calc R . .
C26 C -0.07875(19) 0.16492(9) -0.05153(12) 0.0232(5) Uani 1 1 d . . .
H26A H -0.1563 0.1374 -0.0573 0.028 Uiso 1 1 calc R . .
H26B H -0.0868 0.1991 -0.0055 0.028 Uiso 1 1 calc R . .
C27 C 0.03658(19) 0.12262(9) -0.01826(13) 0.0259(5) Uani 1 1 d . . .
H27A H 0.1148 0.1493 -0.0160 0.031 Uiso 1 1 calc R . .
H27B H 0.0415 0.0865 -0.0620 0.031 Uiso 1 1 calc R . .
C28 C 0.0307(2) 0.09405(9) 0.07551(13) 0.0275(5) Uani 1 1 d . . .
H28A H 0.0291 0.1303 0.1195 0.033 Uiso 1 1 calc R . .
H28B H -0.0495 0.0690 0.0737 0.033 Uiso 1 1 calc R . .
C29 C 0.14150(19) 0.04972(9) 0.10815(14) 0.0290(5) Uani 1 1 d . . .
H29A H 0.1325 0.0311 0.1684 0.035 Uiso 1 1 calc R . .
H29B H 0.1450 0.0132 0.0648 0.035 Uiso 1 1 calc R . .
C30 C 0.3677(2) 0.05627(10) 0.11551(13) 0.0277(5) Uani 1 1 d . . .
C31 C 0.4712(2) 0.09435(10) 0.10221(14) 0.0323(5) Uani 1 1 d . . .
C32 C 0.5879(2) 0.06672(12) 0.09817(15) 0.0389(6) Uani 1 1 d . . .
C33 C 0.6037(2) -0.00021(13) 0.10689(14) 0.0397(6) Uani 1 1 d . . .
C34 C 0.5022(2) -0.03765(11) 0.12192(14) 0.0349(6) Uani 1 1 d . . .
C35 C 0.3840(2) -0.01079(10) 0.12702(13) 0.0314(5) Uani 1 1 d . . .
H35 H 0.3150 -0.0377 0.1382 0.038 Uiso 1 1 calc 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
F1 0.0403(9) 0.0456(8) 0.0531(9) 0.0083(6) 0.0017(7) -0.0103(6)
F2 0.0317(9) 0.0891(11) 0.0543(9) 0.0023(8) 0.0083(7) -0.0126(8)
F3 0.0340(9) 0.0982(12) 0.0378(8) -0.0063(7) 0.0046(6) 0.0231(8)
F4 0.0617(10) 0.0479(8) 0.0408(8) 0.0021(6) 0.0079(7) 0.0234(7)
O1 0.0257(9) 0.0316(8) 0.0335(8) 0.0035(6) 0.0009(7) -0.0004(6)
N1 0.0256(10) 0.0170(8) 0.0168(8) 0.0003(6) 0.0030(7) -0.0001(7)
N2 0.0217(10) 0.0218(9) 0.0180(9) -0.0024(7) 0.0020(7) 0.0011(7)
C1 0.0250(12) 0.0193(10) 0.0160(10) -0.0017(8) 0.0002(8) 0.0008(9)
C2 0.0273(13) 0.0248(11) 0.0194(10) -0.0031(8) 0.0002(9) 0.0018(9)
C3 0.0373(15) 0.0239(11) 0.0277(12) -0.0040(9) 0.0007(10) 0.0079(10)
C4 0.0482(16) 0.0208(11) 0.0253(12) -0.0009(9) 0.0020(11) -0.0029(10)
C5 0.0372(14) 0.0252(11) 0.0251(11) -0.0023(9) 0.0062(10) -0.0067(10)
C6 0.0277(13) 0.0235(10) 0.0179(10) -0.0023(8) 0.0023(9) -0.0005(9)
C7 0.0279(14) 0.0284(11) 0.0321(12) -0.0040(9) 0.0040(10) 0.0065(9)
C8 0.0397(16) 0.0615(16) 0.0373(14) -0.0048(12) 0.0136(12) -0.0010(12)
C9 0.0343(15) 0.0562(15) 0.0486(15) -0.0004(12) -0.0027(12) 0.0086(12)
C10 0.0300(13) 0.0288(11) 0.0323(12) -0.0015(9) 0.0100(10) -0.0008(9)
C11 0.0288(14) 0.0496(15) 0.0479(15) -0.0027(11) 0.0078(11) 0.0019(11)
C12 0.0510(17) 0.0411(13) 0.0440(14) -0.0031(11) 0.0256(12) -0.0002(11)
C13 0.0264(12) 0.0179(10) 0.0164(10) 0.0004(8) 0.0052(9) -0.0046(8)
C14 0.0233(12) 0.0197(10) 0.0205(10) 0.0022(8) 0.0073(9) -0.0031(8)
C15 0.0271(13) 0.0241(10) 0.0248(11) -0.0020(8) 0.0100(9) -0.0020(9)
C16 0.0328(13) 0.0291(11) 0.0189(10) -0.0062(8) 0.0063(10) -0.0045(9)
C17 0.0287(13) 0.0284(11) 0.0208(11) 0.0008(8) 0.0007(9) -0.0003(9)
C18 0.0251(12) 0.0192(10) 0.0191(10) 0.0030(8) 0.0040(9) -0.0003(8)
C19 0.0234(12) 0.0295(11) 0.0227(11) -0.0024(8) 0.0072(9) -0.0017(9)
C20 0.0273(13) 0.0332(12) 0.0353(13) -0.0028(9) 0.0044(10) 0.0005(10)
C21 0.0273(13) 0.0340(12) 0.0390(13) -0.0052(10) 0.0107(10) -0.0032(10)
C22 0.0280(13) 0.0252(10) 0.0218(10) -0.0001(8) -0.0004(9) 0.0027(9)
C23 0.0282(13) 0.0340(12) 0.0365(13) -0.0032(10) 0.0035(10) 0.0039(10)
C24 0.0405(15) 0.0288(12) 0.0408(14) 0.0038(10) 0.0016(11) 0.0064(10)
C25 0.0172(11) 0.0250(11) 0.0164(10) 0.0004(8) 0.0019(8) 0.0032(8)
C26 0.0284(12) 0.0244(10) 0.0173(10) 0.0006(8) 0.0054(9) 0.0016(8)
C27 0.0254(13) 0.0318(11) 0.0207(11) 0.0028(9) 0.0044(9) 0.0006(9)
C28 0.0285(13) 0.0299(11) 0.0241(11) 0.0050(9) 0.0043(9) -0.0016(9)
C29 0.0259(13) 0.0320(11) 0.0284(12) 0.0078(9) 0.0018(9) -0.0030(9)
C30 0.0241(13) 0.0381(13) 0.0200(11) 0.0032(9) 0.0000(9) 0.0007(10)
C31 0.0318(15) 0.0386(13) 0.0247(12) 0.0024(9) -0.0020(10) -0.0030(10)
C32 0.0244(15) 0.0637(17) 0.0283(13) 0.0006(11) 0.0029(10) -0.0067(12)
C33 0.0260(14) 0.0697(17) 0.0222(12) -0.0029(11) -0.0001(10) 0.0124(13)
C34 0.0427(16) 0.0400(13) 0.0211(11) 0.0016(9) 0.0014(10) 0.0119(12)
C35 0.0319(14) 0.0391(13) 0.0229(11) 0.0045(9) 0.0029(10) 0.0047(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
F1 C31 1.353(2) . ?
F2 C32 1.349(3) . ?
F3 C33 1.352(3) . ?
F4 C34 1.353(2) . ?
O1 C30 1.357(2) . ?
O1 C29 1.444(2) . ?
N1 C25 1.358(2) . ?
N1 C1 1.440(2) . ?
N1 C26 1.472(2) . ?
N2 C25 1.277(2) . ?
N2 C13 1.428(2) . ?
C1 C6 1.399(3) . ?
C1 C2 1.408(3) . ?
C2 C3 1.393(3) . ?
C2 C7 1.514(3) . ?
C3 C4 1.378(3) . ?
C4 C5 1.381(3) . ?
C5 C6 1.395(3) . ?
C6 C10 1.519(3) . ?
C7 C9 1.525(3) . ?
C7 C8 1.537(3) . ?
C10 C11 1.528(3) . ?
C10 C12 1.537(3) . ?
C13 C18 1.401(3) . ?
C13 C14 1.417(3) . ?
C14 C15 1.396(3) . ?
C14 C19 1.515(3) . ?
C15 C16 1.381(3) . ?
C16 C17 1.373(3) . ?
C17 C18 1.403(3) . ?
C18 C22 1.518(3) . ?
C19 C20 1.528(3) . ?
C19 C21 1.529(3) . ?
C22 C23 1.530(3) . ?
C22 C24 1.539(3) . ?
C26 C27 1.520(3) . ?
C27 C28 1.521(3) . ?
C28 C29 1.506(3) . ?
C30 C31 1.383(3) . ?
C30 C35 1.388(3) . ?
C31 C32 1.370(3) . ?
C32 C33 1.381(3) . ?
C33 C34 1.367(3) . ?
C34 C35 1.381(3) . ?

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
C30 O1 C29 117.21(16) . . ?
C25 N1 C1 119.12(14) . . ?
C25 N1 C26 120.03(14) . . ?
C1 N1 C26 119.98(14) . . ?
C25 N2 C13 117.55(15) . . ?
C6 C1 C2 121.91(17) . . ?
C6 C1 N1 119.93(17) . . ?
C2 C1 N1 118.15(17) . . ?
C3 C2 C1 117.96(19) . . ?
C3 C2 C7 119.66(18) . . ?
C1 C2 C7 122.36(17) . . ?
C4 C3 C2 120.9(2) . . ?
C3 C4 C5 120.42(19) . . ?
C4 C5 C6 121.2(2) . . ?
C5 C6 C1 117.68(18) . . ?
C5 C6 C10 118.84(19) . . ?
C1 C6 C10 123.48(17) . . ?
C2 C7 C9 110.75(18) . . ?
C2 C7 C8 111.97(17) . . ?
C9 C7 C8 110.47(19) . . ?
C6 C10 C11 111.48(17) . . ?
C6 C10 C12 111.09(17) . . ?
C11 C10 C12 110.67(19) . . ?
C18 C13 C14 121.02(16) . . ?
C18 C13 N2 121.29(17) . . ?
C14 C13 N2 117.59(16) . . ?
C15 C14 C13 118.16(17) . . ?
C15 C14 C19 121.56(18) . . ?
C13 C14 C19 120.10(16) . . ?
C16 C15 C14 121.23(19) . . ?
C17 C16 C15 119.94(18) . . ?
C16 C17 C18 121.63(19) . . ?
C13 C18 C17 118.03(18) . . ?
C13 C18 C22 122.76(16) . . ?
C17 C18 C22 119.17(17) . . ?
C14 C19 C20 114.59(15) . . ?
C14 C19 C21 109.50(15) . . ?
C20 C19 C21 110.15(17) . . ?
C18 C22 C23 113.10(15) . . ?
C18 C22 C24 110.08(17) . . ?
C23 C22 C24 109.22(16) . . ?
N2 C25 N1 123.44(17) . . ?
N1 C26 C27 113.31(16) . . ?
C26 C27 C28 112.06(17) . . ?
C29 C28 C27 112.92(17) . . ?
O1 C29 C28 107.38(15) . . ?
O1 C30 C31 115.79(18) . . ?
O1 C30 C35 125.14(19) . . ?
C31 C30 C35 119.1(2) . . ?
F1 C31 C32 118.7(2) . . ?
F1 C31 C30 120.2(2) . . ?
C32 C31 C30 121.1(2) . . ?
F2 C32 C31 120.4(2) . . ?
F2 C32 C33 119.4(2) . . ?
C31 C32 C33 120.1(2) . . ?
F3 C33 C34 121.6(2) . . ?
F3 C33 C32 119.6(2) . . ?
C34 C33 C32 118.7(2) . . ?
F4 C34 C33 118.5(2) . . ?
F4 C34 C35 119.4(2) . . ?
C33 C34 C35 122.1(2) . . ?
C34 C35 C30 118.8(2) . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        28.13
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.057