# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2013


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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
# 
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#  fide research purposes only. It may contain copyright material 
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data_zv02
_database_code_depnum_ccdc_archive 'CCDC 775425'
#TrackingRef 'zv02.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H39 F6 N3 O8'
_chemical_formula_sum            'C29 H39 F6 N3 O8'
_chemical_formula_weight         671.63
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'P 21 21 21 '
_symmetry_space_group_name_Hall  'P 2ac 2ab '
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
_cell_length_a                   14.698(2)
_cell_length_b                   14.698(1)
_cell_length_c                   15.598(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3369.5(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    20393
_cell_measurement_theta_min      2.352
_cell_measurement_theta_max      20.235
_chemical_absolute_configuration rm
_exptl_crystal_description       'elongated table'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1408
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker, 1997'
_exptl_absorpt_correction_T_min  0.9528
_exptl_absorpt_correction_T_max  0.9862
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      296(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  'Bruker APEX-II CCD area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_standards_decay_%        0.00
_diffrn_reflns_number            95977
_diffrn_reflns_av_R_equivalents  0.0662
_diffrn_reflns_av_sigmaI/netI    0.0369
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         26.41
_reflns_number_total             3841
_reflns_number_gt                2287
_reflns_threshold_expression     >2\s(I)
_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    
;
M.C. Burla, M. Camalli, B. Carrozzini, G.L. Cascarano, C. Giacovazzo,
G. Polidori, R. Spagna (2003).
SIR2002: the program. J. Appl. Cryst. 36,1103
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
ORTEP-III (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565)
and Mercury 1.4.2, CCDC
;
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_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^ > 2\s(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.
The structure was collected at R.T. the benzyl, hexafluoroisopropyl, the
ether methyl group and the two methyl groups on acetal moiety are
disordered. Several splitting models have been performed for the C27 and C8
but no one has given a satified results, the correlation were too high.
We decided to no-split C27 and C26. The benzyl group was splitted. The
hexafluoroisopropyl and the ether methyl group (C24) were not splitted.
The hydrogen H3N was refined in different model but all of them put the
hydrogen close to H21B.
;
_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^)+(0.0902P)^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    noref
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0062(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3841
_refine_ls_number_parameters     477
_refine_ls_number_restraints     239
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.1320
_refine_ls_wR_factor_gt          0.1157
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_restrained_S_all      0.954
_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
C1A C 1.0118(10) 1.2010(9) 0.9816(8) 0.073(2) Uani 0.50 1 d PDU A 1
C2A C 1.0793(8) 1.1811(10) 1.0379(9) 0.078(2) Uani 0.50 1 d PDU A 1
H2A H 1.0779 1.1259 1.0671 0.093 Uiso 0.50 1 calc PR A 1
C3A C 1.1486(9) 1.2399(9) 1.0524(10) 0.090(3) Uani 0.50 1 d PDU A 1
H3A H 1.1926 1.2260 1.0932 0.108 Uiso 0.50 1 calc PR A 1
C4A C 1.1539(9) 1.3186(8) 1.0079(7) 0.093(2) Uani 0.50 1 d PDU A 1
H4A H 1.2033 1.3574 1.0156 0.112 Uiso 0.50 1 calc PR A 1
C5A C 1.0870(6) 1.3406(7) 0.9520(7) 0.091(2) Uani 0.50 1 d PDU A 1
H5A H 1.0882 1.3959 0.9231 0.110 Uiso 0.50 1 calc PR A 1
C6A C 1.0181(6) 1.2808(6) 0.9388(7) 0.080(2) Uani 0.50 1 d PDU A 1
H6A H 0.9735 1.2953 0.8988 0.096 Uiso 0.50 1 calc PR A 1
C1B C 1.0142(9) 1.2006(8) 0.9970(9) 0.075(2) Uani 0.50 1 d PDU A 2
C2B C 1.0987(8) 1.1723(9) 1.0248(9) 0.076(2) Uani 0.50 1 d PDU A 2
H2B H 1.1092 1.1107 1.0338 0.091 Uiso 0.50 1 calc PR A 2
C3B C 1.1678(9) 1.2338(8) 1.0396(10) 0.086(2) Uani 0.50 1 d PDU A 2
H3B H 1.2261 1.2134 1.0526 0.103 Uiso 0.50 1 calc PR A 2
C4B C 1.1497(9) 1.3254(8) 1.0349(8) 0.095(2) Uani 0.50 1 d PDU A 2
H4B H 1.1924 1.3674 1.0541 0.115 Uiso 0.50 1 calc PR A 2
C5B C 1.0682(7) 1.3546(7) 1.0016(8) 0.103(2) Uani 0.50 1 d PDU A 2
H5B H 1.0598 1.4154 0.9873 0.123 Uiso 0.50 1 calc PR A 2
C6B C 0.9990(7) 1.2926(6) 0.9895(8) 0.094(2) Uani 0.50 1 d PDU A 2
H6B H 0.9409 1.3134 0.9761 0.113 Uiso 0.50 1 calc PR A 2
C7 C 0.9348(3) 1.1373(3) 0.9763(4) 0.0920(14) Uani 1 1 d . . .
H7A H 0.9063 1.1307 1.0320 0.110 Uiso 1 1 calc R A 1
H7B H 0.8897 1.1597 0.9361 0.110 Uiso 1 1 calc R A 1
O1 O 0.97020(16) 1.05124(17) 0.9478(2) 0.0754(8) Uani 1 1 d . A .
C8 C 0.9084(2) 0.9880(2) 0.9303(2) 0.0599(9) Uani 1 1 d . . .
O2 O 0.82825(18) 1.00141(18) 0.9330(2) 0.0849(9) Uani 1 1 d . A .
C9 C 0.9528(2) 0.9000(2) 0.9051(3) 0.0576(9) Uani 1 1 d . A .
H9 H 0.9943 0.8818 0.9512 0.069 Uiso 1 1 calc R . .
C10 C 1.0068(3) 0.9085(3) 0.8238(3) 0.0904(14) Uani 1 1 d . . .
H10A H 0.9665 0.9214 0.7770 0.136 Uiso 1 1 calc R A .
H10B H 1.0384 0.8524 0.8130 0.136 Uiso 1 1 calc R . .
H10C H 1.0501 0.9570 0.8296 0.136 Uiso 1 1 calc R . .
N1 N 0.88183(17) 0.83221(18) 0.89872(19) 0.0542(7) Uani 1 1 d . . .
H1 H 0.8302 0.8473 0.8771 0.065 Uiso 1 1 calc R A .
C11 C 0.8941(2) 0.7472(2) 0.9253(2) 0.0460(7) Uani 1 1 d . A .
O3 O 0.96902(13) 0.71453(15) 0.94127(15) 0.0551(6) Uani 1 1 d . . .
C12 C 0.80542(18) 0.6901(2) 0.9298(2) 0.0435(7) Uani 1 1 d . . .
H12 H 0.7847 0.6823 0.8706 0.052 Uiso 1 1 calc R A .
C13 C 0.8291(2) 0.5940(2) 0.9633(2) 0.0564(9) Uani 1 1 d . A .
H13 H 0.8800 0.6005 1.0034 0.068 Uiso 1 1 calc R . .
C14 C 0.7536(3) 0.5476(3) 1.0103(3) 0.0757(12) Uani 1 1 d . . .
F1 F 0.67452(14) 0.54634(16) 0.9682(2) 0.0937(8) Uani 1 1 d . A .
F2 F 0.77435(19) 0.46260(17) 1.0298(2) 0.1164(11) Uani 1 1 d . A .
F3 F 0.73653(19) 0.5875(2) 1.08546(19) 0.1045(9) Uani 1 1 d . A .
C15 C 0.8612(3) 0.5343(3) 0.8908(4) 0.0878(14) Uani 1 1 d . . .
F4 F 0.89944(17) 0.5800(2) 0.82604(19) 0.0992(9) Uani 1 1 d . A .
F5 F 0.7944(2) 0.4887(3) 0.8540(3) 0.1546(16) Uani 1 1 d . A .
F6 F 0.9216(3) 0.4750(2) 0.9128(3) 0.1679(17) Uani 1 1 d . A .
N2 N 0.73328(15) 0.73641(18) 0.97434(15) 0.0437(6) Uani 1 1 d . A .
C16 C 0.7547(2) 0.7732(2) 1.0539(2) 0.0486(8) Uani 1 1 d D . .
O4 O 0.83319(14) 0.76802(18) 1.07941(14) 0.0649(7) Uani 1 1 d . A .
N3 N 0.68629(18) 0.8101(2) 1.09858(18) 0.0577(8) Uani 1 1 d D A .
H3N H 0.6314(10) 0.799(2) 1.085(2) 0.069 Uiso 1 1 d D . .
C17 C 0.6986(3) 0.8577(3) 1.1804(2) 0.0711(11) Uani 1 1 d D . .
C18 C 0.6044(3) 0.8857(4) 1.2093(4) 0.125(2) Uani 1 1 d . A .
H18A H 0.5684 0.8324 1.2200 0.187 Uiso 1 1 calc R . .
H18B H 0.5760 0.9215 1.1652 0.187 Uiso 1 1 calc R . .
H18C H 0.6089 0.9211 1.2608 0.187 Uiso 1 1 calc R . .
C19 C 0.7573(4) 0.9399(4) 1.1676(4) 0.125(2) Uani 1 1 d . A .
H19A H 0.7249 0.9841 1.1341 0.187 Uiso 1 1 calc R . .
H19B H 0.8120 0.9227 1.1381 0.187 Uiso 1 1 calc R . .
H19C H 0.7725 0.9656 1.2223 0.187 Uiso 1 1 calc R . .
C20 C 0.7384(4) 0.7951(4) 1.2465(3) 0.1084(18) Uani 1 1 d . A .
H20A H 0.8005 0.7818 1.2319 0.163 Uiso 1 1 calc R . .
H20B H 0.7041 0.7395 1.2480 0.163 Uiso 1 1 calc R . .
H20C H 0.7362 0.8238 1.3017 0.163 Uiso 1 1 calc R . .
C21 C 0.64313(18) 0.7440(2) 0.93444(19) 0.0426(7) Uani 1 1 d . . .
H21A H 0.5969 0.7340 0.9778 0.051 Uiso 1 1 calc R A .
H21B H 0.6368 0.6966 0.8916 0.051 Uiso 1 1 calc R . .
C22 C 0.62683(19) 0.8357(2) 0.8924(2) 0.0492(8) Uani 1 1 d . A .
H22 H 0.6301 0.8836 0.9359 0.059 Uiso 1 1 calc R . .
O5 O 0.69429(13) 0.85252(16) 0.82738(14) 0.0550(6) Uani 1 1 d . . .
C23 C 0.6597(2) 0.8234(3) 0.7479(2) 0.0609(9) Uani 1 1 d . A .
H23 H 0.6856 0.8600 0.7014 0.073 Uiso 1 1 calc R . .
O6 O 0.6791(2) 0.73162(19) 0.73484(19) 0.0862(8) Uani 1 1 d . . .
C24 C 0.7561(4) 0.7128(5) 0.6863(4) 0.142(3) Uani 1 1 d . A .
H24A H 0.7632 0.6482 0.6808 0.212 Uiso 1 1 calc R . .
H24B H 0.8087 0.7380 0.7140 0.212 Uiso 1 1 calc R . .
H24C H 0.7496 0.7394 0.6304 0.212 Uiso 1 1 calc R . .
C25 C 0.5588(2) 0.8375(3) 0.7525(2) 0.0606(9) Uani 1 1 d . . .
H25 H 0.5249 0.7900 0.7221 0.073 Uiso 1 1 calc R A .
O7 O 0.53906(19) 0.9244(2) 0.72157(19) 0.0880(9) Uani 1 1 d . A .
C26 C 0.4795(3) 0.9670(3) 0.7804(3) 0.0811(13) Uani 1 1 d . . .
C27 C 0.3820(3) 0.9544(6) 0.7551(4) 0.164(4) Uani 1 1 d . A .
H27A H 0.3716 0.9826 0.7005 0.245 Uiso 1 1 calc R . .
H27B H 0.3434 0.9820 0.7974 0.245 Uiso 1 1 calc R . .
H27C H 0.3687 0.8906 0.7513 0.245 Uiso 1 1 calc R . .
C28 C 0.5039(6) 1.0660(5) 0.7878(8) 0.219(6) Uani 1 1 d . A .
H28A H 0.4944 1.0954 0.7336 0.328 Uiso 1 1 calc R . .
H28B H 0.5667 1.0716 0.8041 0.328 Uiso 1 1 calc R . .
H28C H 0.4663 1.0941 0.8305 0.328 Uiso 1 1 calc R . .
O8 O 0.4941(2) 0.9261(2) 0.85981(19) 0.0954(10) Uani 1 1 d . A .
C29 C 0.5357(2) 0.8411(3) 0.8468(2) 0.0540(9) Uani 1 1 d . A .
H29 H 0.4955 0.7909 0.8634 0.065 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
C1A 0.067(4) 0.054(4) 0.099(5) -0.013(4) -0.017(4) 0.004(3)
C2A 0.077(5) 0.067(4) 0.089(5) -0.014(4) -0.014(4) 0.003(4)
C3A 0.091(5) 0.084(4) 0.096(5) -0.026(4) -0.025(4) 0.003(4)
C4A 0.094(4) 0.077(4) 0.109(5) -0.034(4) -0.006(4) -0.008(4)
C5A 0.094(4) 0.068(4) 0.113(5) -0.011(4) 0.000(4) 0.007(4)
C6A 0.079(4) 0.060(4) 0.102(5) -0.003(4) -0.019(4) 0.010(3)
C1B 0.069(4) 0.055(4) 0.101(5) -0.008(4) -0.014(4) 0.005(3)
C2B 0.071(4) 0.063(4) 0.093(5) -0.012(4) -0.015(4) 0.006(4)
C3B 0.084(4) 0.081(4) 0.093(5) -0.024(4) -0.017(4) 0.003(4)
C4B 0.099(4) 0.083(4) 0.105(5) -0.018(4) -0.017(4) -0.012(4)
C5B 0.107(4) 0.074(4) 0.127(5) -0.010(5) -0.023(5) -0.003(4)
C6B 0.087(4) 0.067(4) 0.127(5) -0.003(4) -0.024(4) 0.005(4)
C7 0.078(3) 0.058(3) 0.140(4) -0.018(3) -0.005(3) 0.006(2)
O1 0.0560(14) 0.0487(15) 0.122(2) -0.0108(15) -0.0047(15) -0.0030(12)
C8 0.050(2) 0.049(2) 0.081(2) 0.0086(19) -0.0053(17) -0.0039(17)
O2 0.0503(16) 0.0686(17) 0.136(3) -0.0109(18) -0.0013(15) 0.0041(12)
C9 0.0386(16) 0.048(2) 0.086(3) 0.014(2) -0.0042(16) -0.0066(15)
C10 0.083(3) 0.062(3) 0.126(4) 0.010(3) 0.039(3) 0.000(2)
N1 0.0398(13) 0.0449(17) 0.0780(19) 0.0124(15) -0.0140(13) -0.0052(12)
C11 0.0422(17) 0.044(2) 0.0514(17) 0.0003(16) -0.0067(14) -0.0020(14)
O3 0.0351(11) 0.0494(13) 0.0808(16) 0.0013(12) -0.0036(10) 0.0015(10)
C12 0.0357(15) 0.0417(17) 0.0530(17) -0.0017(15) -0.0045(13) 0.0024(13)
C13 0.0419(17) 0.0404(18) 0.087(2) 0.0058(18) -0.0136(17) -0.0015(15)
C14 0.072(3) 0.051(2) 0.105(4) 0.021(2) -0.017(2) -0.0016(19)
F1 0.0579(13) 0.0733(15) 0.150(2) 0.0311(15) -0.0168(14) -0.0206(11)
F2 0.1087(18) 0.0557(15) 0.185(3) 0.0493(18) -0.031(2) -0.0146(14)
F3 0.114(2) 0.0992(19) 0.100(2) 0.0420(18) 0.0057(17) -0.0186(16)
C15 0.060(2) 0.058(3) 0.145(4) -0.021(3) -0.020(3) 0.006(2)
F4 0.0807(16) 0.094(2) 0.123(2) -0.0423(18) 0.0151(15) 0.0049(15)
F5 0.116(2) 0.139(3) 0.209(4) -0.101(3) 0.017(2) -0.055(2)
F6 0.161(3) 0.107(2) 0.236(4) -0.013(3) -0.013(3) 0.088(3)
N2 0.0360(12) 0.0491(15) 0.0460(15) 0.0014(13) -0.0079(11) 0.0005(11)
C16 0.0439(18) 0.0500(19) 0.0519(19) -0.0014(16) -0.0125(15) 0.0007(15)
O4 0.0438(13) 0.0851(18) 0.0658(14) -0.0091(13) -0.0188(11) 0.0048(12)
N3 0.0457(15) 0.0725(19) 0.0547(16) -0.0188(15) -0.0103(13) 0.0082(15)
C17 0.072(2) 0.082(3) 0.059(2) -0.026(2) -0.0197(19) 0.015(2)
C18 0.107(4) 0.164(6) 0.103(4) -0.076(4) -0.025(3) 0.056(4)
C19 0.155(5) 0.079(3) 0.140(5) -0.029(3) -0.052(4) -0.019(3)
C20 0.125(4) 0.142(5) 0.058(2) -0.017(3) -0.015(3) 0.041(4)
C21 0.0344(14) 0.0479(18) 0.0455(16) 0.0019(15) -0.0078(12) -0.0004(13)
C22 0.0435(17) 0.052(2) 0.0519(19) -0.0003(16) -0.0104(15) 0.0014(15)
O5 0.0396(11) 0.0597(14) 0.0657(15) 0.0137(12) -0.0073(11) -0.0100(11)
C23 0.063(2) 0.061(2) 0.059(2) 0.0122(19) 0.0025(17) -0.0015(18)
O6 0.102(2) 0.0670(18) 0.0898(19) -0.0003(16) 0.0292(17) 0.0102(16)
C24 0.168(6) 0.135(6) 0.122(5) -0.014(4) 0.068(4) 0.030(5)
C25 0.056(2) 0.067(2) 0.059(2) 0.006(2) -0.0112(17) -0.0062(18)
O7 0.0770(19) 0.103(2) 0.0843(18) 0.0404(18) 0.0016(16) 0.0228(17)
C26 0.059(2) 0.076(3) 0.108(3) 0.040(3) -0.006(2) 0.014(2)
C27 0.059(3) 0.319(11) 0.113(4) 0.052(6) -0.019(3) 0.034(5)
C28 0.181(7) 0.081(5) 0.394(17) 0.031(7) 0.078(10) 0.003(5)
O8 0.104(2) 0.100(2) 0.083(2) -0.0041(18) -0.0246(17) 0.0626(19)
C29 0.0455(17) 0.060(2) 0.056(2) 0.0077(17) -0.0090(15) 0.0078(17)
_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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
C1A C6A 1.353(8) . ?
C1A C2A 1.357(8) . ?
C1A C7 1.472(15) . ?
C2A C3A 1.355(8) . ?
C2A H2A 0.9300 . ?
C3A C4A 1.353(8) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.353(8) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.356(8) . ?
C5A H5A 0.9300 . ?
C6A H6A 0.9300 . ?
C1B C6B 1.376(8) . ?
C1B C2B 1.379(8) . ?
C1B C7 1.526(15) . ?
C2B C3B 1.378(8) . ?
C2B H2B 0.9300 . ?
C3B C4B 1.375(8) . ?
C3B H3B 0.9300 . ?
C4B C5B 1.375(8) . ?
C4B H4B 0.9300 . ?
C5B C6B 1.378(8) . ?
C5B H5B 0.9300 . ?
C6B H6B 0.9300 . ?
C7 O1 1.438(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
O1 C8 1.328(4) . ?
C8 O2 1.195(4) . ?
C8 C9 1.502(5) . ?
C9 N1 1.446(4) . ?
C9 C10 1.502(6) . ?
C9 H9 0.9800 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
N1 C11 1.329(4) . ?
N1 H1 0.8600 . ?
C11 O3 1.226(4) . ?
C11 C12 1.552(4) . ?
C12 N2 1.439(4) . ?
C12 C13 1.545(5) . ?
C12 H12 0.9800 . ?
C13 C14 1.495(5) . ?
C13 C15 1.507(6) . ?
C13 H13 0.9800 . ?
C14 F2 1.322(4) . ?
C14 F3 1.334(5) . ?
C14 F1 1.335(4) . ?
C15 F6 1.290(5) . ?
C15 F5 1.320(5) . ?
C15 F4 1.337(6) . ?
N2 C16 1.390(4) . ?
N2 C21 1.468(4) . ?
C16 O4 1.223(4) . ?
C16 N3 1.338(4) . ?
N3 C17 1.467(5) . ?
N3 H3N 0.849(10) . ?
C17 C19 1.499(7) . ?
C17 C20 1.500(6) . ?
C17 C18 1.513(6) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.519(5) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 O5 1.439(4) . ?
C22 C29 1.519(4) . ?
C22 H22 0.9800 . ?
O5 C23 1.407(4) . ?
C23 O6 1.393(5) . ?
C23 C25 1.499(5) . ?
C23 H23 0.9800 . ?
O6 C24 1.389(6) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 O7 1.395(5) . ?
C25 C29 1.511(5) . ?
C25 H25 0.9800 . ?
O7 C26 1.414(5) . ?
C26 O8 1.394(5) . ?
C26 C27 1.498(6) . ?
C26 C28 1.502(9) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
O8 C29 1.406(5) . ?
C29 H29 0.9800 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6A C1A C2A 117.2(9) . . ?
C6A C1A C7 125.2(9) . . ?
C2A C1A C7 117.4(8) . . ?
C3A C2A C1A 121.3(8) . . ?
C3A C2A H2A 119.4 . . ?
C1A C2A H2A 119.4 . . ?
C4A C3A C2A 120.3(7) . . ?
C4A C3A H3A 119.9 . . ?
C2A C3A H3A 119.9 . . ?
C3A C4A C5A 119.5(7) . . ?
C3A C4A H4A 120.2 . . ?
C5A C4A H4A 120.2 . . ?
C4A C5A C6A 119.1(7) . . ?
C4A C5A H5A 120.4 . . ?
C6A C5A H5A 120.4 . . ?
C1A C6A C5A 122.5(8) . . ?
C1A C6A H6A 118.8 . . ?
C5A C6A H6A 118.8 . . ?
C6B C1B C2B 117.9(9) . . ?
C6B C1B C7 117.2(8) . . ?
C2B C1B C7 124.9(8) . . ?
C3B C2B C1B 121.3(8) . . ?
C3B C2B H2B 119.4 . . ?
C1B C2B H2B 119.4 . . ?
C4B C3B C2B 119.4(7) . . ?
C4B C3B H3B 120.3 . . ?
C2B C3B H3B 120.3 . . ?
C3B C4B C5B 119.6(7) . . ?
C3B C4B H4B 120.2 . . ?
C5B C4B H4B 120.2 . . ?
C4B C5B C6B 119.3(7) . . ?
C4B C5B H5B 120.4 . . ?
C6B C5B H5B 120.4 . . ?
C1B C6B C5B 121.2(8) . . ?
C1B C6B H6B 119.4 . . ?
C5B C6B H6B 119.4 . . ?
O1 C7 C1A 107.4(6) . . ?
O1 C7 C1B 109.0(5) . . ?
O1 C7 H7A 110.2 . . ?
C1A C7 H7A 110.2 . . ?
C1B C7 H7A 101.6 . . ?
O1 C7 H7B 110.2 . . ?
C1A C7 H7B 110.2 . . ?
C1B C7 H7B 116.9 . . ?
H7A C7 H7B 108.5 . . ?
C8 O1 C7 115.6(3) . . ?
O2 C8 O1 123.5(3) . . ?
O2 C8 C9 125.5(3) . . ?
O1 C8 C9 111.0(3) . . ?
N1 C9 C10 112.4(3) . . ?
N1 C9 C8 107.3(3) . . ?
C10 C9 C8 112.3(3) . . ?
N1 C9 H9 108.2 . . ?
C10 C9 H9 108.2 . . ?
C8 C9 H9 108.2 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C11 N1 C9 121.9(3) . . ?
C11 N1 H1 119.1 . . ?
C9 N1 H1 119.1 . . ?
O3 C11 N1 123.6(3) . . ?
O3 C11 C12 122.2(3) . . ?
N1 C11 C12 114.1(3) . . ?
N2 C12 C13 115.8(3) . . ?
N2 C12 C11 112.7(2) . . ?
C13 C12 C11 108.7(2) . . ?
N2 C12 H12 106.3 . . ?
C13 C12 H12 106.3 . . ?
C11 C12 H12 106.3 . . ?
C14 C13 C15 109.6(4) . . ?
C14 C13 C12 114.5(3) . . ?
C15 C13 C12 110.5(3) . . ?
C14 C13 H13 107.3 . . ?
C15 C13 H13 107.3 . . ?
C12 C13 H13 107.3 . . ?
F2 C14 F3 104.8(4) . . ?
F2 C14 F1 107.5(3) . . ?
F3 C14 F1 105.9(4) . . ?
F2 C14 C13 111.9(4) . . ?
F3 C14 C13 111.8(3) . . ?
F1 C14 C13 114.3(4) . . ?
F6 C15 F5 106.5(4) . . ?
F6 C15 F4 104.6(4) . . ?
F5 C15 F4 103.9(5) . . ?
F6 C15 C13 114.1(5) . . ?
F5 C15 C13 112.9(4) . . ?
F4 C15 C13 113.9(3) . . ?
C16 N2 C12 116.6(2) . . ?
C16 N2 C21 123.6(3) . . ?
C12 N2 C21 119.8(2) . . ?
O4 C16 N3 124.4(3) . . ?
O4 C16 N2 118.7(3) . . ?
N3 C16 N2 116.9(3) . . ?
C16 N3 C17 123.7(3) . . ?
C16 N3 H3N 121(2) . . ?
C17 N3 H3N 115(2) . . ?
N3 C17 C19 109.8(4) . . ?
N3 C17 C20 110.7(3) . . ?
C19 C17 C20 111.2(4) . . ?
N3 C17 C18 106.0(3) . . ?
C19 C17 C18 110.3(4) . . ?
C20 C17 C18 108.7(4) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N2 C21 C22 113.1(2) . . ?
N2 C21 H21A 109.0 . . ?
C22 C21 H21A 109.0 . . ?
N2 C21 H21B 109.0 . . ?
C22 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
O5 C22 C21 110.4(2) . . ?
O5 C22 C29 105.6(2) . . ?
C21 C22 C29 112.8(3) . . ?
O5 C22 H22 109.3 . . ?
C21 C22 H22 109.3 . . ?
C29 C22 H22 109.3 . . ?
C23 O5 C22 108.6(2) . . ?
O6 C23 O5 110.4(3) . . ?
O6 C23 C25 110.1(3) . . ?
O5 C23 C25 105.9(3) . . ?
O6 C23 H23 110.1 . . ?
O5 C23 H23 110.1 . . ?
C25 C23 H23 110.1 . . ?
C24 O6 C23 116.0(4) . . ?
O6 C24 H24A 109.5 . . ?
O6 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O6 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O7 C25 C23 108.5(3) . . ?
O7 C25 C29 105.0(3) . . ?
C23 C25 C29 105.9(3) . . ?
O7 C25 H25 112.4 . . ?
C23 C25 H25 112.4 . . ?
C29 C25 H25 112.4 . . ?
C25 O7 C26 108.1(3) . . ?
O8 C26 O7 106.9(3) . . ?
O8 C26 C27 109.1(4) . . ?
O7 C26 C27 111.5(5) . . ?
O8 C26 C28 108.2(6) . . ?
O7 C26 C28 109.4(5) . . ?
C27 C26 C28 111.6(6) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C26 O8 C29 108.8(3) . . ?
O8 C29 C25 105.6(3) . . ?
O8 C29 C22 111.2(3) . . ?
C25 C29 C22 104.8(3) . . ?
O8 C29 H29 111.6 . . ?
C25 C29 H29 111.6 . . ?
C22 C29 H29 111.6 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6A C1A C2A C3A 1.9(14) . . . . ?
C7 C1A C2A C3A -174.1(11) . . . . ?
C1A C2A C3A C4A -2.9(14) . . . . ?
C2A C3A C4A C5A 3.5(19) . . . . ?
C3A C4A C5A C6A -3.2(18) . . . . ?
C2A C1A C6A C5A -1.6(18) . . . . ?
C7 C1A C6A C5A 174.0(11) . . . . ?
C4A C5A C6A C1A 2.4(17) . . . . ?
C6B C1B C2B C3B -4.0(15) . . . . ?
C7 C1B C2B C3B 177.9(12) . . . . ?
C1B C2B C3B C4B 6.6(14) . . . . ?
C2B C3B C4B C5B -11(2) . . . . ?
C3B C4B C5B C6B 13(2) . . . . ?
C2B C1B C6B C5B 6(2) . . . . ?
C7 C1B C6B C5B -175.8(12) . . . . ?
C4B C5B C6B C1B -11(2) . . . . ?
C6A C1A C7 O1 122.0(12) . . . . ?
C2A C1A C7 O1 -62.4(12) . . . . ?
C6A C1A C7 C1B -137(7) . . . . ?
C2A C1A C7 C1B 39(5) . . . . ?
C6B C1B C7 O1 152.9(11) . . . . ?
C2B C1B C7 O1 -29.0(14) . . . . ?
C6B C1B C7 C1A 71(5) . . . . ?
C2B C1B C7 C1A -111(6) . . . . ?
C1A C7 O1 C8 -172.9(6) . . . . ?
C1B C7 O1 C8 177.6(6) . . . . ?
C7 O1 C8 O2 4.1(6) . . . . ?
C7 O1 C8 C9 -177.4(4) . . . . ?
O2 C8 C9 N1 -9.1(6) . . . . ?
O1 C8 C9 N1 172.4(3) . . . . ?
O2 C8 C9 C10 114.9(5) . . . . ?
O1 C8 C9 C10 -63.6(4) . . . . ?
C10 C9 N1 C11 95.1(4) . . . . ?
C8 C9 N1 C11 -141.0(3) . . . . ?
C9 N1 C11 O3 -14.7(5) . . . . ?
C9 N1 C11 C12 168.6(3) . . . . ?
O3 C11 C12 N2 134.1(3) . . . . ?
N1 C11 C12 N2 -49.1(4) . . . . ?
O3 C11 C12 C13 4.4(4) . . . . ?
N1 C11 C12 C13 -178.9(3) . . . . ?
N2 C12 C13 C14 23.8(4) . . . . ?
C11 C12 C13 C14 151.8(3) . . . . ?
N2 C12 C13 C15 148.1(3) . . . . ?
C11 C12 C13 C15 -83.9(3) . . . . ?
C15 C13 C14 F2 48.9(5) . . . . ?
C12 C13 C14 F2 173.7(3) . . . . ?
C15 C13 C14 F3 166.1(3) . . . . ?
C12 C13 C14 F3 -69.1(4) . . . . ?
C15 C13 C14 F1 -73.6(4) . . . . ?
C12 C13 C14 F1 51.2(5) . . . . ?
C14 C13 C15 F6 -85.6(5) . . . . ?
C12 C13 C15 F6 147.3(4) . . . . ?
C14 C13 C15 F5 36.1(5) . . . . ?
C12 C13 C15 F5 -91.0(5) . . . . ?
C14 C13 C15 F4 154.3(3) . . . . ?
C12 C13 C15 F4 27.2(4) . . . . ?
C13 C12 N2 C16 76.2(3) . . . . ?
C11 C12 N2 C16 -49.8(4) . . . . ?
C13 C12 N2 C21 -104.8(3) . . . . ?
C11 C12 N2 C21 129.3(3) . . . . ?
C12 N2 C16 O4 3.3(4) . . . . ?
C21 N2 C16 O4 -175.7(3) . . . . ?
C12 N2 C16 N3 -174.9(3) . . . . ?
C21 N2 C16 N3 6.1(4) . . . . ?
O4 C16 N3 C17 6.5(6) . . . . ?
N2 C16 N3 C17 -175.3(3) . . . . ?
C16 N3 C17 C19 62.4(5) . . . . ?
C16 N3 C17 C20 -60.7(5) . . . . ?
C16 N3 C17 C18 -178.5(4) . . . . ?
C16 N2 C21 C22 79.4(4) . . . . ?
C12 N2 C21 C22 -99.6(3) . . . . ?
N2 C21 C22 O5 58.8(3) . . . . ?
N2 C21 C22 C29 176.6(3) . . . . ?
C21 C22 O5 C23 93.6(3) . . . . ?
C29 C22 O5 C23 -28.6(3) . . . . ?
C22 O5 C23 O6 -87.8(3) . . . . ?
C22 O5 C23 C25 31.4(4) . . . . ?
O5 C23 O6 C24 -96.4(4) . . . . ?
C25 C23 O6 C24 147.1(4) . . . . ?
O6 C23 C25 O7 -149.7(3) . . . . ?
O5 C23 C25 O7 90.9(3) . . . . ?
O6 C23 C25 C29 98.1(4) . . . . ?
O5 C23 C25 C29 -21.3(4) . . . . ?
C23 C25 O7 C26 -132.3(3) . . . . ?
C29 C25 O7 C26 -19.4(4) . . . . ?
C25 O7 C26 O8 25.1(4) . . . . ?
C25 O7 C26 C27 -94.1(5) . . . . ?
C25 O7 C26 C28 142.0(6) . . . . ?
O7 C26 O8 C29 -20.3(4) . . . . ?
C27 C26 O8 C29 100.4(5) . . . . ?
C28 C26 O8 C29 -137.9(5) . . . . ?
C26 O8 C29 C25 8.1(4) . . . . ?
C26 O8 C29 C22 121.3(3) . . . . ?
O7 C25 C29 O8 7.0(4) . . . . ?
C23 C25 C29 O8 121.7(3) . . . . ?
O7 C25 C29 C22 -110.5(3) . . . . ?
C23 C25 C29 C22 4.2(4) . . . . ?
O5 C22 C29 O8 -99.7(3) . . . . ?
C21 C22 C29 O8 139.7(3) . . . . ?
O5 C22 C29 C25 13.9(4) . . . . ?
C21 C22 C29 C25 -106.7(3) . . . . ?
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        26.41
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.049


data_zv03_2
_database_code_depnum_ccdc_archive 'CCDC 892811'
#TrackingRef 'zv03_2.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H35 F6 N3 O4'
_chemical_formula_sum            'C21 H35 F6 N3 O4'
_chemical_formula_weight         507.52
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   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
_cell_length_a                   11.1300(10)
_cell_length_b                   17.4990(10)
_cell_length_c                   14.0510(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.900(3)
_cell_angle_gamma                90.00
_cell_volume                     2695.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2738
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      20.56
_chemical_absolute_configuration rm
_exptl_crystal_description       table
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.10
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_max          0.16
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1072
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.'
_exptl_absorpt_correction_T_min  0.6463
_exptl_absorpt_correction_T_max  0.7454
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      173(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  'Bruker APEX-II CCD area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_reflns_number            16750
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_sigmaI/netI    0.0924
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.86
_diffrn_reflns_theta_max         26.37
_reflns_number_total             5393
_reflns_number_gt                3401
_reflns_threshold_expression     >2\s(I)
_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    
;
SUPERFLIP (L. Palatinus and G. Chapuis (2007) J. Appl. Cryst 40, 786-790'
;
_computing_structure_refinement  
'SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)'
_computing_molecular_graphics    
;
ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565)
Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E.,
Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006).
J. Appl. Cryst. 39, 453-457
;
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_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^ > 2\s(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^)+(0.0469P)^2^+0.1413P] 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    noref
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5393
_refine_ls_number_parameters     634
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1055
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1081
_refine_ls_wR_factor_gt          0.0915
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_iucr_refine_instructions_details 
;
TITL zv03_2
CELL 0.71073 11.130 17.499 14.051 90.000 99.900 90.000
ZERR 4 0.001 0.001 0.001 0.000 0.003 0.000
LATT -1
SYMM -X,1/2+Y,-Z
SFAC C H N O F
UNIT 84 140 12 16 24
L.S. 8
FMAP 2
PLAN 50
ACTA
BOND $H
TEMP -100
MERG 3
CONF
SADI 0.01 N3 H3
SADI 0.02 C19 H3 C18 H3
WGHT 0.046900 0.141200
WGHT 0.0469 0.1413
FVAR 0.16749
Mole 1
C1 1 0.231513 0.763306 -0.165139 11.00000 0.03362 0.03328 =
0.06961 0.01324 -0.00123 0.00234
AFIX 137
H1A 2 0.169977 0.733475 -0.207849 11.00000 -1.50000
H1B 2 0.295819 0.779115 -0.200641 11.00000 -1.50000
H1C 2 0.193207 0.808683 -0.142471 11.00000 -1.50000
AFIX 0
C2 1 0.389602 0.756735 -0.014122 11.00000 0.04598 0.01959 =
0.06623 -0.00334 -0.00355 0.00192
AFIX 137
H2A 2 0.455099 0.767977 -0.050549 11.00000 -1.50000
H2B 2 0.421414 0.724490 0.041549 11.00000 -1.50000
H2C 2 0.358486 0.804621 0.008445 11.00000 -1.50000
AFIX 0
C3 1 0.189842 0.685791 -0.025551 11.00000 0.04793 0.03577 =
0.08799 -0.00840 0.03503 0.00229
AFIX 137
H3A 2 0.228282 0.656350 0.030874 11.00000 -1.50000
H3B 2 0.132937 0.652961 -0.068245 11.00000 -1.50000
H3C 2 0.145382 0.729140 -0.004285 11.00000 -1.50000
AFIX 0
C4 1 0.286444 0.714842 -0.079279 11.00000 0.03559 0.01844 =
0.05080 0.00223 0.01067 0.00325
O1 4 0.338060 0.649545 -0.126237 11.00000 0.02772 0.02329 =
0.03919 0.00594 0.00812 0.00171
C5 1 0.403718 0.595705 -0.075167 11.00000 0.02820 0.01429 =
0.03189 0.00102 0.01033 -0.00312
O2 4 0.423065 0.590082 0.011736 11.00000 0.05713 0.02919 =
0.02491 0.00251 0.01269 0.01118
C6 1 0.452063 0.539285 -0.142518 11.00000 0.02430 0.03136 =
0.02069 0.00553 0.00738 0.00073
AFIX 13
H6 2 0.454284 0.565748 -0.205270 11.00000 -1.20000
AFIX 0
C7 1 0.370500 0.468347 -0.163113 11.00000 0.04091 0.03313 =
0.04083 -0.01465 0.01095 -0.00644
AFIX 13
H7 2 0.410794 0.433461 -0.204411 11.00000 -1.20000
AFIX 0
C8 1 0.246430 0.489895 -0.221508 11.00000 0.04338 0.06527 =
0.05419 -0.01988 -0.00084 -0.01182
AFIX 137
H8A 2 0.258206 0.520227 -0.277810 11.00000 -1.50000
H8B 2 0.200598 0.519947 -0.181007 11.00000 -1.50000
H8C 2 0.200876 0.443338 -0.243174 11.00000 -1.50000
AFIX 0
C9 1 0.357404 0.423736 -0.071473 11.00000 0.04140 0.02926 =
0.07801 0.00260 0.01818 -0.00897
AFIX 137
H9A 2 0.303954 0.379587 -0.088843 11.00000 -1.50000
H9B 2 0.322028 0.457037 -0.027479 11.00000 -1.50000
H9C 2 0.437863 0.406086 -0.039552 11.00000 -1.50000
AFIX 0
N1 3 0.576025 0.518575 -0.100124 11.00000 0.02485 0.01681 =
0.02817 0.00155 0.00751 0.00286
AFIX 43
H1 2 0.590104 0.473604 -0.072422 11.00000 -1.20000
AFIX 0
C10 1 0.668286 0.565840 -0.102231 11.00000 0.02353 0.01831 =
0.01871 -0.00573 0.00873 -0.00083
O3 4 0.660158 0.625384 -0.150192 11.00000 0.03588 0.02404 =
0.02118 0.00616 0.00842 -0.00105
C11 1 0.792087 0.545672 -0.039476 11.00000 0.02741 0.02189 =
0.02505 0.00254 0.01603 -0.00120
AFIX 13
H11 2 0.849248 0.587185 -0.051760 11.00000 -1.20000
AFIX 0
C12 1 0.849271 0.470196 -0.069690 11.00000 0.02973 0.02606 =
0.02778 0.00056 0.01164 0.00708
AFIX 13
H12 2 0.791935 0.427554 -0.061905 11.00000 -1.20000
AFIX 0
C13 1 0.970432 0.451793 -0.008752 11.00000 0.04237 0.03265 =
0.03530 0.00379 0.01261 0.02193
C14 1 0.861790 0.473686 -0.175630 11.00000 0.05656 0.04387 =
0.03055 -0.00357 0.01831 0.01415
F1 5 0.752937 0.479912 -0.232584 11.00000 0.05902 0.07727 =
0.02035 -0.00740 0.00538 0.02774
F2 5 0.912997 0.412007 -0.206438 11.00000 0.10059 0.09161 =
0.03485 -0.00606 0.02629 0.06253
F3 5 0.926819 0.534031 -0.195202 11.00000 0.09105 0.09969 =
0.04182 0.00812 0.03892 -0.01854
F4 5 1.023232 0.389170 -0.036798 11.00000 0.04876 0.05033 =
0.04740 -0.00449 0.01011 0.03064
F5 5 0.962403 0.439265 0.083907 11.00000 0.05629 0.06789 =
0.02487 0.01007 0.00935 0.03034
F6 5 1.051012 0.508218 -0.008135 11.00000 0.03540 0.05781 =
0.07383 0.00693 0.00136 -0.00021
N2 3 0.785795 0.550684 0.063916 11.00000 0.02430 0.01587 =
0.01745 0.00202 0.00940 -0.00293
C15 1 0.814739 0.626023 0.114621 11.00000 0.03661 0.02194 =
0.02776 -0.00524 0.01212 -0.01137
AFIX 13
H15 2 0.833860 0.614831 0.185403 11.00000 -1.20000
AFIX 0
C16 1 0.704184 0.679245 0.099000 11.00000 0.05122 0.01887 =
0.02767 0.00064 0.01456 0.00462
AFIX 137
H16A 2 0.635183 0.653829 0.120644 11.00000 -1.50000
H16B 2 0.682439 0.691703 0.030191 11.00000 -1.50000
H16C 2 0.724053 0.726324 0.136150 11.00000 -1.50000
AFIX 0
C17 1 0.926051 0.664392 0.087901 11.00000 0.05427 0.04227 =
0.04701 -0.01207 0.02734 -0.02583
AFIX 137
H17A 2 0.906603 0.683799 0.021613 11.00000 -1.50000
H17B 2 0.992768 0.627298 0.092508 11.00000 -1.50000
H17C 2 0.950922 0.706946 0.132267 11.00000 -1.50000
AFIX 0
C18 1 0.720293 0.496173 0.103315 11.00000 0.01643 0.01729 =
0.02299 0.00217 0.00292 0.00402
O4 4 0.684603 0.436731 0.056000 11.00000 0.03623 0.01459 =
0.01946 -0.00193 0.01009 -0.00159
N3 3 0.692954 0.506670 0.192221 11.00000 0.03051 0.01709 =
0.01442 -0.00400 0.00995 -0.00106
H3 2 0.704787 0.546770 0.222238 11.00000 -1.20000
C19 1 0.618630 0.452621 0.236532 11.00000 0.02827 0.02038 =
0.02033 0.00406 0.00936 -0.00468
AFIX 13
H19 2 0.596149 0.409300 0.190499 11.00000 -1.20000
AFIX 0
C20 1 0.502402 0.491656 0.252212 11.00000 0.02600 0.03272 =
0.04316 -0.00122 0.01184 -0.00410
AFIX 137
H20A 2 0.455948 0.507859 0.189820 11.00000 -1.50000
H20B 2 0.522631 0.536440 0.293757 11.00000 -1.50000
H20C 2 0.453301 0.455967 0.283221 11.00000 -1.50000
AFIX 0
C21 1 0.692643 0.420643 0.328779 11.00000 0.04657 0.03026 =
0.02394 0.00276 0.01034 -0.00173
AFIX 137
H21A 2 0.720588 0.462671 0.373197 11.00000 -1.50000
H21B 2 0.763353 0.392871 0.313432 11.00000 -1.50000
H21C 2 0.641767 0.385743 0.359257 11.00000 -1.50000
AFIX 0
Mole 2
C22 1 1.193356 0.524045 0.450853 11.00000 0.03902 0.04272 =
0.12692 -0.01140 -0.02583 0.01204
AFIX 137
H22A 2 1.144642 0.524413 0.502694 11.00000 -1.50000
H22B 2 1.250223 0.567248 0.459291 11.00000 -1.50000
H22C 2 1.239339 0.476125 0.453178 11.00000 -1.50000
AFIX 0
C23 1 1.182059 0.538061 0.272832 11.00000 0.04808 0.04453 =
0.12861 -0.01920 0.05800 0.00225
AFIX 137
H23A 2 1.237364 0.581930 0.284500 11.00000 -1.50000
H23B 2 1.125132 0.545622 0.212140 11.00000 -1.50000
H23C 2 1.229515 0.491399 0.268514 11.00000 -1.50000
AFIX 0
C24 1 1.019189 0.466869 0.337550 11.00000 0.03369 0.03426 =
0.05607 -0.01445 0.01187 -0.00187
AFIX 137
H24A 2 0.963928 0.475909 0.276374 11.00000 -1.50000
H24B 2 0.972124 0.464976 0.390387 11.00000 -1.50000
H24C 2 1.061749 0.418178 0.334151 11.00000 -1.50000
AFIX 0
C25 1 1.110965 0.530662 0.355573 11.00000 0.01728 0.02918 =
0.07226 -0.01373 0.00496 0.00748
O5 4 1.046940 0.605986 0.349431 11.00000 0.02821 0.02822 =
0.04354 -0.00670 0.01024 0.00694
C26 1 0.974913 0.624866 0.413184 11.00000 0.02018 0.03177 =
0.02552 -0.00645 0.00174 -0.00002
O6 4 0.951639 0.585259 0.477594 11.00000 0.05284 0.03307 =
0.03049 0.00363 0.00701 0.01233
C27 1 0.929792 0.706444 0.393055 11.00000 0.02256 0.02698 =
0.02131 0.00040 0.00497 0.00709
AFIX 13
H27 2 0.909490 0.713294 0.321433 11.00000 -1.20000
AFIX 0
C28 1 1.027230 0.765033 0.432602 11.00000 0.02246 0.03632 =
0.03873 -0.00710 0.01122 -0.00129
AFIX 13
H28 2 1.099136 0.754523 0.400617 11.00000 -1.20000
AFIX 0
C29 1 1.071821 0.757193 0.541738 11.00000 0.04609 0.04603 =
0.03861 -0.00915 -0.00561 -0.00462
AFIX 137
H29A 2 1.004242 0.767807 0.576226 11.00000 -1.50000
H29B 2 1.138027 0.793666 0.562253 11.00000 -1.50000
H29C 2 1.101670 0.705099 0.556430 11.00000 -1.50000
AFIX 0
C30 1 0.986840 0.846706 0.405873 11.00000 0.04868 0.03389 =
0.05661 -0.00722 0.02274 -0.01087
AFIX 137
H30A 2 1.056070 0.881482 0.423698 11.00000 -1.50000
H30B 2 0.921126 0.861198 0.440619 11.00000 -1.50000
H30C 2 0.957381 0.849899 0.336132 11.00000 -1.50000
AFIX 0
N4 3 0.819055 0.719056 0.432930 11.00000 0.02294 0.02363 =
0.01911 -0.00571 0.00936 0.00222
AFIX 43
H4 2 0.818245 0.752934 0.479100 11.00000 -1.20000
AFIX 0
C31 1 0.719487 0.679267 0.399352 11.00000 0.02840 0.01463 =
0.01972 0.00624 0.00335 0.00220
O7 4 0.710920 0.632511 0.332973 11.00000 0.03401 0.01789 =
0.01638 -0.00561 0.00426 -0.00193
C32 1 0.608574 0.693119 0.450852 11.00000 0.02484 0.01504 =
0.01660 -0.00051 0.00278 -0.00412
AFIX 13
H32 2 0.551341 0.649841 0.430188 11.00000 -1.20000
AFIX 0
C33 1 0.535503 0.766932 0.415929 11.00000 0.02849 0.02241 =
0.01996 0.00064 0.00661 0.00054
AFIX 13
H33 2 0.585390 0.811720 0.443663 11.00000 -1.20000
AFIX 0
C34 1 0.415286 0.770691 0.451409 11.00000 0.03543 0.03407 =
0.03542 0.00092 0.01095 0.00613
C35 1 0.514609 0.774716 0.306464 11.00000 0.02633 0.03490 =
0.03267 0.00727 0.01062 0.00847
F7 5 0.620267 0.788627 0.275896 11.00000 0.03875 0.04279 =
0.03986 0.01826 0.02235 0.01023
F8 5 0.469076 0.711066 0.261544 11.00000 0.04893 0.04718 =
0.02557 -0.00725 -0.00348 -0.00137
F9 5 0.441047 0.831793 0.273135 11.00000 0.04626 0.05307 =
0.03603 0.01909 0.01123 0.02259
F10 5 0.428725 0.767768 0.548275 11.00000 0.04108 0.05978 =
0.03083 0.00297 0.02017 0.01250
F11 5 0.340157 0.713044 0.417666 11.00000 0.02956 0.06132 =
0.05576 -0.00747 0.01562 -0.01070
F12 5 0.353335 0.835254 0.426501 11.00000 0.04586 0.05536 =
0.04919 0.00880 0.02022 0.02840
N5 3 0.639863 0.686667 0.555755 11.00000 0.02783 0.01391 =
0.01632 -0.00052 0.00802 -0.00608
C36 1 0.621545 0.610539 0.598851 11.00000 0.03982 0.01724 =
0.01819 -0.00009 0.00864 -0.00880
AFIX 13
H36 2 0.667506 0.611125 0.666578 11.00000 -1.20000
AFIX 0
C37 1 0.676154 0.547127 0.545479 11.00000 0.07604 0.01722 =
0.02637 0.00059 0.01315 -0.00491
AFIX 137
H37A 2 0.760235 0.560398 0.539999 11.00000 -1.50000
H37B 2 0.627702 0.541057 0.480761 11.00000 -1.50000
H37C 2 0.675661 0.499125 0.581337 11.00000 -1.50000
AFIX 0
C38 1 0.488424 0.596066 0.604751 11.00000 0.04319 0.04889 =
0.03451 0.00644 0.00913 -0.02380
AFIX 137
H38A 2 0.439705 0.597430 0.539667 11.00000 -1.50000
H38B 2 0.459459 0.635636 0.644682 11.00000 -1.50000
H38C 2 0.480246 0.545797 0.633710 11.00000 -1.50000
AFIX 0
C39 1 0.689036 0.748202 0.609781 11.00000 0.02208 0.02010 =
0.02222 0.00206 0.01012 0.00196
O8 4 0.729467 0.804011 0.570504 11.00000 0.02950 0.01659 =
0.02058 0.00064 0.00859 -0.00365
N7A 3 0.688989 0.747219 0.705862 11.00000 0.03059 0.02343 =
0.02044 -0.00225 0.01157 -0.01053
AFIX 43
H7A 2 0.644733 0.712973 0.730015 11.00000 -1.20000
AFIX 0
C40 1 0.760953 0.801885 0.770384 11.00000 0.03113 0.01872 =
0.02141 -0.00481 0.00744 -0.00719
AFIX 13
H40 2 0.765886 0.850485 0.733815 11.00000 -1.20000
AFIX 0
C41 1 0.698090 0.818990 0.855508 11.00000 0.04440 0.02946 =
0.02246 -0.00184 0.01072 0.00241
AFIX 137
H41A 2 0.694605 0.772369 0.893582 11.00000 -1.50000
H41B 2 0.615099 0.837283 0.831888 11.00000 -1.50000
H41C 2 0.743921 0.858378 0.896091 11.00000 -1.50000
AFIX 0
C42 1 0.889247 0.771902 0.801555 11.00000 0.03370 0.04526 =
0.03769 -0.01178 0.00789 -0.00871
AFIX 137
H42A 2 0.927422 0.763834 0.744495 11.00000 -1.50000
H42B 2 0.886323 0.723360 0.835865 11.00000 -1.50000
H42C 2 0.937063 0.809099 0.844487 11.00000 -1.50000
MOLE 5
HKLF 4
REM zv03_2
REM R1 = 0.0499 for 3401 Fo > 4sig(Fo) and 0.1055 for all 5393 data
REM 634 parameters refined using 2 restraints
END
;
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 0.2315(5) 0.7633(3) -0.1651(4) 0.0467(15) Uani 1 1 d . . .
H1A H 0.1700 0.7335 -0.2078 0.070 Uiso 1 1 calc R . .
H1B H 0.2958 0.7791 -0.2006 0.070 Uiso 1 1 calc R . .
H1C H 0.1932 0.8087 -0.1425 0.070 Uiso 1 1 calc R . .
C2 C 0.3896(5) 0.7567(3) -0.0141(4) 0.0455(15) Uani 1 1 d . . .
H2A H 0.4551 0.7680 -0.0505 0.068 Uiso 1 1 calc R . .
H2B H 0.4214 0.7245 0.0415 0.068 Uiso 1 1 calc R . .
H2C H 0.3585 0.8046 0.0084 0.068 Uiso 1 1 calc R . .
C3 C 0.1898(5) 0.6858(3) -0.0256(5) 0.0545(17) Uani 1 1 d . . .
H3A H 0.2283 0.6564 0.0309 0.082 Uiso 1 1 calc R . .
H3B H 0.1329 0.6530 -0.0682 0.082 Uiso 1 1 calc R . .
H3C H 0.1454 0.7291 -0.0043 0.082 Uiso 1 1 calc R . .
C4 C 0.2864(5) 0.7148(3) -0.0793(4) 0.0346(13) Uani 1 1 d . . .
O1 O 0.3381(3) 0.64954(17) -0.1262(2) 0.0298(8) Uani 1 1 d . . .
C5 C 0.4037(4) 0.5957(3) -0.0752(4) 0.0242(11) Uani 1 1 d . . .
O2 O 0.4231(3) 0.59008(18) 0.0117(2) 0.0364(9) Uani 1 1 d . . .
C6 C 0.4521(4) 0.5393(3) -0.1425(3) 0.0250(11) Uani 1 1 d . . .
H6 H 0.4543 0.5657 -0.2053 0.030 Uiso 1 1 calc R . .
C7 C 0.3705(5) 0.4683(3) -0.1631(4) 0.0378(14) Uani 1 1 d . . .
H7 H 0.4108 0.4335 -0.2044 0.045 Uiso 1 1 calc R . .
C8 C 0.2464(5) 0.4899(4) -0.2215(4) 0.0554(17) Uani 1 1 d . . .
H8A H 0.2582 0.5202 -0.2778 0.083 Uiso 1 1 calc R . .
H8B H 0.2006 0.5199 -0.1810 0.083 Uiso 1 1 calc R . .
H8C H 0.2009 0.4433 -0.2432 0.083 Uiso 1 1 calc R . .
C9 C 0.3574(5) 0.4237(3) -0.0715(4) 0.0486(16) Uani 1 1 d . . .
H9A H 0.3040 0.3796 -0.0888 0.073 Uiso 1 1 calc R . .
H9B H 0.3220 0.4570 -0.0275 0.073 Uiso 1 1 calc R . .
H9C H 0.4379 0.4061 -0.0396 0.073 Uiso 1 1 calc R . .
N1 N 0.5760(3) 0.5186(2) -0.1001(3) 0.0229(9) Uani 1 1 d . . .
H1 H 0.5901 0.4736 -0.0724 0.028 Uiso 1 1 calc R . .
C10 C 0.6683(4) 0.5658(3) -0.1022(3) 0.0196(11) Uani 1 1 d . . .
O3 O 0.6602(3) 0.62538(18) -0.1502(2) 0.0266(8) Uani 1 1 d . . .
C11 C 0.7921(4) 0.5457(3) -0.0395(3) 0.0234(11) Uani 1 1 d . . .
H11 H 0.8492 0.5872 -0.0518 0.028 Uiso 1 1 calc R . .
C12 C 0.8493(4) 0.4702(3) -0.0697(3) 0.0271(12) Uani 1 1 d . . .
H12 H 0.7919 0.4276 -0.0619 0.032 Uiso 1 1 calc R . .
C13 C 0.9704(5) 0.4518(3) -0.0088(4) 0.0361(13) Uani 1 1 d . . .
C14 C 0.8618(6) 0.4737(3) -0.1756(4) 0.0424(15) Uani 1 1 d . . .
F1 F 0.7529(3) 0.4799(2) -0.23258(19) 0.0524(9) Uani 1 1 d . . .
F2 F 0.9130(4) 0.4120(2) -0.2064(2) 0.0740(12) Uani 1 1 d . . .
F3 F 0.9268(4) 0.5340(2) -0.1952(2) 0.0743(12) Uani 1 1 d . . .
F4 F 1.0232(3) 0.38917(17) -0.0368(2) 0.0486(9) Uani 1 1 d . . .
F5 F 0.9624(3) 0.43926(19) 0.08391(19) 0.0494(9) Uani 1 1 d . . .
F6 F 1.0510(3) 0.50822(19) -0.0081(2) 0.0566(9) Uani 1 1 d . . .
N2 N 0.7858(3) 0.5507(2) 0.0639(2) 0.0185(9) Uani 1 1 d . . .
C15 C 0.8147(4) 0.6260(3) 0.1146(3) 0.0280(12) Uani 1 1 d . . .
H15 H 0.8339 0.6148 0.1854 0.034 Uiso 1 1 calc R . .
C16 C 0.7042(5) 0.6792(3) 0.0990(3) 0.0317(13) Uani 1 1 d . . .
H16A H 0.6352 0.6538 0.1206 0.047 Uiso 1 1 calc R . .
H16B H 0.6824 0.6917 0.0302 0.047 Uiso 1 1 calc R . .
H16C H 0.7241 0.7263 0.1362 0.047 Uiso 1 1 calc R . .
C17 C 0.9261(5) 0.6644(3) 0.0879(4) 0.0456(16) Uani 1 1 d . . .
H17A H 0.9066 0.6838 0.0216 0.068 Uiso 1 1 calc R . .
H17B H 0.9928 0.6273 0.0925 0.068 Uiso 1 1 calc R . .
H17C H 0.9509 0.7069 0.1323 0.068 Uiso 1 1 calc R . .
C18 C 0.7203(4) 0.4962(3) 0.1033(3) 0.0190(10) Uani 1 1 d D . .
O4 O 0.6846(3) 0.43673(16) 0.0560(2) 0.0228(7) Uani 1 1 d . . .
N3 N 0.6930(3) 0.5067(2) 0.1922(2) 0.0200(9) Uani 1 1 d . . .
H3 H 0.705(4) 0.547(3) 0.222(2) 0.024 Uiso 1 1 d D . .
C19 C 0.6186(4) 0.4526(3) 0.2365(3) 0.0224(11) Uani 1 1 d D . .
H19 H 0.5961 0.4093 0.1905 0.027 Uiso 1 1 calc R . .
C20 C 0.5024(4) 0.4917(3) 0.2522(4) 0.0333(13) Uani 1 1 d . . .
H20A H 0.4559 0.5079 0.1898 0.050 Uiso 1 1 calc R . .
H20B H 0.5226 0.5364 0.2938 0.050 Uiso 1 1 calc R . .
H20C H 0.4533 0.4560 0.2832 0.050 Uiso 1 1 calc R . .
C21 C 0.6926(5) 0.4206(3) 0.3288(3) 0.0331(13) Uani 1 1 d . . .
H21A H 0.7206 0.4627 0.3732 0.050 Uiso 1 1 calc R . .
H21B H 0.7634 0.3929 0.3134 0.050 Uiso 1 1 calc R . .
H21C H 0.6418 0.3857 0.3593 0.050 Uiso 1 1 calc R . .
C22 C 1.1934(6) 0.5240(4) 0.4509(5) 0.074(2) Uani 1 1 d . . .
H22A H 1.1446 0.5244 0.5027 0.111 Uiso 1 1 calc R . .
H22B H 1.2502 0.5672 0.4593 0.111 Uiso 1 1 calc R . .
H22C H 1.2393 0.4761 0.4532 0.111 Uiso 1 1 calc R . .
C23 C 1.1821(6) 0.5381(4) 0.2728(5) 0.069(2) Uani 1 1 d . . .
H23A H 1.2374 0.5819 0.2845 0.103 Uiso 1 1 calc R . .
H23B H 1.1251 0.5456 0.2121 0.103 Uiso 1 1 calc R . .
H23C H 1.2295 0.4914 0.2685 0.103 Uiso 1 1 calc R . .
C24 C 1.0192(5) 0.4669(3) 0.3375(4) 0.0409(14) Uani 1 1 d . . .
H24A H 0.9639 0.4759 0.2764 0.061 Uiso 1 1 calc R . .
H24B H 0.9721 0.4650 0.3904 0.061 Uiso 1 1 calc R . .
H24C H 1.0617 0.4182 0.3342 0.061 Uiso 1 1 calc R . .
C25 C 1.1110(4) 0.5307(3) 0.3556(4) 0.0399(14) Uani 1 1 d . . .
O5 O 1.0469(3) 0.60599(18) 0.3494(2) 0.0328(8) Uani 1 1 d . . .
C26 C 0.9749(4) 0.6249(3) 0.4132(3) 0.0261(11) Uani 1 1 d . . .
O6 O 0.9516(3) 0.5853(2) 0.4776(2) 0.0388(9) Uani 1 1 d . . .
C27 C 0.9298(4) 0.7064(3) 0.3931(3) 0.0235(11) Uani 1 1 d . . .
H27 H 0.9095 0.7133 0.3214 0.028 Uiso 1 1 calc R . .
C28 C 1.0272(4) 0.7650(3) 0.4326(3) 0.0318(12) Uani 1 1 d . . .
H28 H 1.0991 0.7545 0.4006 0.038 Uiso 1 1 calc R . .
C29 C 1.0718(5) 0.7572(3) 0.5417(3) 0.0451(15) Uani 1 1 d . . .
H29A H 1.0042 0.7678 0.5762 0.068 Uiso 1 1 calc R . .
H29B H 1.1380 0.7937 0.5623 0.068 Uiso 1 1 calc R . .
H29C H 1.1017 0.7051 0.5564 0.068 Uiso 1 1 calc R . .
C30 C 0.9868(5) 0.8467(3) 0.4059(4) 0.0448(15) Uani 1 1 d . . .
H30A H 1.0561 0.8815 0.4237 0.067 Uiso 1 1 calc R . .
H30B H 0.9211 0.8612 0.4406 0.067 Uiso 1 1 calc R . .
H30C H 0.9574 0.8499 0.3361 0.067 Uiso 1 1 calc R . .
N4 N 0.8191(3) 0.7191(2) 0.4329(2) 0.0212(9) Uani 1 1 d . . .
H4 H 0.8182 0.7529 0.4791 0.025 Uiso 1 1 calc R . .
C31 C 0.7195(4) 0.6793(3) 0.3994(3) 0.0210(11) Uani 1 1 d . . .
O7 O 0.7109(3) 0.63251(17) 0.3330(2) 0.0228(7) Uani 1 1 d . . .
C32 C 0.6086(4) 0.6931(2) 0.4509(3) 0.0189(11) Uani 1 1 d . . .
H32 H 0.5513 0.6498 0.4302 0.023 Uiso 1 1 calc R . .
C33 C 0.5355(4) 0.7669(3) 0.4159(3) 0.0233(11) Uani 1 1 d . . .
H33 H 0.5854 0.8117 0.4437 0.028 Uiso 1 1 calc R . .
C34 C 0.4153(5) 0.7707(3) 0.4514(4) 0.0344(13) Uani 1 1 d . . .
C35 C 0.5146(4) 0.7747(3) 0.3065(3) 0.0306(12) Uani 1 1 d . . .
F7 F 0.6203(3) 0.78863(16) 0.27590(19) 0.0386(8) Uani 1 1 d . . .
F8 F 0.4691(3) 0.71107(17) 0.26154(19) 0.0417(8) Uani 1 1 d . . .
F9 F 0.4410(3) 0.83179(17) 0.2731(2) 0.0446(8) Uani 1 1 d . . .
F10 F 0.4287(2) 0.76777(18) 0.54828(19) 0.0422(8) Uani 1 1 d . . .
F11 F 0.3402(3) 0.71304(19) 0.4177(2) 0.0479(8) Uani 1 1 d . . .
F12 F 0.3533(3) 0.83525(18) 0.4265(2) 0.0487(9) Uani 1 1 d . . .
N5 N 0.6399(3) 0.68667(19) 0.5558(2) 0.0189(9) Uani 1 1 d . . .
C36 C 0.6215(4) 0.6105(2) 0.5989(3) 0.0247(11) Uani 1 1 d . . .
H36 H 0.6675 0.6111 0.6666 0.030 Uiso 1 1 calc R . .
C37 C 0.6762(6) 0.5471(3) 0.5455(4) 0.0394(14) Uani 1 1 d . . .
H37A H 0.7602 0.5604 0.5400 0.059 Uiso 1 1 calc R . .
H37B H 0.6277 0.5411 0.4808 0.059 Uiso 1 1 calc R . .
H37C H 0.6757 0.4991 0.5813 0.059 Uiso 1 1 calc R . .
C38 C 0.4884(5) 0.5961(3) 0.6048(4) 0.0419(14) Uani 1 1 d . . .
H38A H 0.4397 0.5974 0.5397 0.063 Uiso 1 1 calc R . .
H38B H 0.4595 0.6356 0.6447 0.063 Uiso 1 1 calc R . .
H38C H 0.4802 0.5458 0.6337 0.063 Uiso 1 1 calc R . .
C39 C 0.6890(4) 0.7482(3) 0.6098(3) 0.0207(11) Uani 1 1 d . . .
O8 O 0.7295(3) 0.80401(16) 0.5705(2) 0.0217(7) Uani 1 1 d . . .
N7A N 0.6890(3) 0.7472(2) 0.7059(2) 0.0240(9) Uani 1 1 d . . .
H7A H 0.6447 0.7130 0.7300 0.029 Uiso 1 1 calc R . .
C40 C 0.7610(4) 0.8019(3) 0.7704(3) 0.0234(11) Uani 1 1 d . . .
H40 H 0.7659 0.8505 0.7338 0.028 Uiso 1 1 calc R . .
C41 C 0.6981(5) 0.8190(3) 0.8555(3) 0.0315(12) Uani 1 1 d . . .
H41A H 0.6946 0.7724 0.8936 0.047 Uiso 1 1 calc R . .
H41B H 0.6151 0.8373 0.8319 0.047 Uiso 1 1 calc R . .
H41C H 0.7439 0.8584 0.8961 0.047 Uiso 1 1 calc R . .
C42 C 0.8892(4) 0.7719(3) 0.8016(4) 0.0387(13) Uani 1 1 d . . .
H42A H 0.9274 0.7638 0.7445 0.058 Uiso 1 1 calc R . .
H42B H 0.8863 0.7234 0.8359 0.058 Uiso 1 1 calc R . .
H42C H 0.9371 0.8091 0.8445 0.058 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
C1 0.034(3) 0.033(3) 0.070(4) 0.013(3) -0.001(3) 0.002(3)
C2 0.046(4) 0.020(3) 0.066(4) -0.003(3) -0.004(3) 0.002(3)
C3 0.048(4) 0.036(4) 0.088(5) -0.008(3) 0.035(4) 0.002(3)
C4 0.036(3) 0.018(3) 0.051(3) 0.002(3) 0.011(3) 0.003(2)
O1 0.0277(19) 0.0233(19) 0.039(2) 0.0059(16) 0.0081(16) 0.0017(16)
C5 0.028(3) 0.014(3) 0.032(3) 0.001(2) 0.010(2) -0.003(2)
O2 0.057(2) 0.029(2) 0.025(2) 0.0025(16) 0.0127(18) 0.0112(18)
C6 0.024(3) 0.031(3) 0.021(2) 0.006(2) 0.007(2) 0.001(2)
C7 0.041(3) 0.033(3) 0.041(3) -0.015(3) 0.011(3) -0.006(3)
C8 0.043(4) 0.065(4) 0.054(4) -0.020(3) -0.001(3) -0.012(3)
C9 0.041(4) 0.029(3) 0.078(4) 0.003(3) 0.018(3) -0.009(3)
N1 0.025(2) 0.017(2) 0.028(2) 0.0016(17) 0.0075(18) 0.0029(19)
C10 0.024(3) 0.018(3) 0.019(2) -0.006(2) 0.009(2) -0.001(2)
O3 0.036(2) 0.0240(19) 0.0212(17) 0.0062(16) 0.0084(15) -0.0011(16)
C11 0.027(3) 0.022(3) 0.025(3) 0.003(2) 0.016(2) -0.001(2)
C12 0.030(3) 0.026(3) 0.028(3) 0.001(2) 0.012(2) 0.007(2)
C13 0.042(4) 0.033(3) 0.035(3) 0.004(3) 0.013(3) 0.022(3)
C14 0.057(4) 0.044(4) 0.031(3) -0.004(3) 0.018(3) 0.014(3)
F1 0.059(2) 0.077(2) 0.0203(15) -0.0074(16) 0.0054(15) 0.0277(19)
F2 0.101(3) 0.092(3) 0.0348(19) -0.0061(18) 0.0263(19) 0.063(2)
F3 0.091(3) 0.100(3) 0.042(2) 0.008(2) 0.039(2) -0.019(3)
F4 0.049(2) 0.050(2) 0.0474(19) -0.0045(16) 0.0101(16) 0.0306(16)
F5 0.056(2) 0.068(2) 0.0249(16) 0.0101(15) 0.0093(14) 0.0303(18)
F6 0.0354(19) 0.058(2) 0.074(2) 0.0069(18) 0.0014(17) -0.0002(18)
N2 0.024(2) 0.016(2) 0.017(2) 0.0020(16) 0.0094(17) -0.0029(17)
C15 0.037(3) 0.022(3) 0.028(3) -0.005(2) 0.012(2) -0.011(2)
C16 0.051(4) 0.019(3) 0.028(3) 0.001(2) 0.015(3) 0.005(3)
C17 0.054(4) 0.042(4) 0.047(4) -0.012(3) 0.027(3) -0.026(3)
C18 0.016(2) 0.017(3) 0.023(3) 0.002(2) 0.003(2) 0.004(2)
O4 0.036(2) 0.0146(18) 0.0195(17) -0.0019(14) 0.0101(14) -0.0016(15)
N3 0.031(2) 0.017(2) 0.014(2) -0.0040(17) 0.0100(18) -0.0011(18)
C19 0.028(3) 0.020(3) 0.020(2) 0.004(2) 0.009(2) -0.005(2)
C20 0.026(3) 0.033(3) 0.043(3) -0.001(3) 0.012(2) -0.004(2)
C21 0.047(3) 0.030(3) 0.024(3) 0.003(2) 0.010(2) -0.002(3)
C22 0.039(4) 0.043(4) 0.127(6) -0.011(4) -0.026(4) 0.012(3)
C23 0.048(4) 0.045(4) 0.129(6) -0.019(4) 0.058(4) 0.002(3)
C24 0.034(3) 0.034(3) 0.056(3) -0.014(3) 0.012(3) -0.002(3)
C25 0.017(3) 0.029(3) 0.072(4) -0.014(3) 0.005(3) 0.007(2)
O5 0.0282(19) 0.028(2) 0.044(2) -0.0067(16) 0.0102(17) 0.0069(16)
C26 0.020(3) 0.032(3) 0.026(3) -0.006(3) 0.002(2) 0.000(2)
O6 0.053(3) 0.033(2) 0.030(2) 0.0036(17) 0.0070(18) 0.0123(18)
C27 0.023(3) 0.027(3) 0.021(3) 0.000(2) 0.005(2) 0.007(2)
C28 0.022(3) 0.036(3) 0.039(3) -0.007(3) 0.011(2) -0.001(2)
C29 0.046(4) 0.046(4) 0.039(3) -0.009(3) -0.006(3) -0.005(3)
C30 0.049(4) 0.034(3) 0.057(4) -0.007(3) 0.023(3) -0.011(3)
N4 0.023(2) 0.024(2) 0.019(2) -0.0057(17) 0.0094(18) 0.0022(19)
C31 0.028(3) 0.015(2) 0.020(3) 0.006(2) 0.003(2) 0.002(2)
O7 0.0340(19) 0.0179(17) 0.0164(16) -0.0056(15) 0.0043(14) -0.0019(15)
C32 0.025(3) 0.015(3) 0.017(2) -0.0005(19) 0.003(2) -0.004(2)
C33 0.028(3) 0.022(3) 0.020(2) 0.001(2) 0.007(2) 0.001(2)
C34 0.035(3) 0.034(3) 0.035(3) 0.001(3) 0.011(3) 0.006(3)
C35 0.026(3) 0.035(3) 0.033(3) 0.007(3) 0.011(2) 0.008(3)
F7 0.0388(18) 0.0428(19) 0.0399(17) 0.0183(14) 0.0224(14) 0.0102(14)
F8 0.049(2) 0.047(2) 0.0256(16) -0.0072(14) -0.0035(14) -0.0014(16)
F9 0.046(2) 0.053(2) 0.0360(17) 0.0191(15) 0.0112(14) 0.0226(17)
F10 0.0411(19) 0.060(2) 0.0308(17) 0.0030(15) 0.0202(14) 0.0125(16)
F11 0.0296(18) 0.061(2) 0.056(2) -0.0075(17) 0.0156(16) -0.0107(16)
F12 0.046(2) 0.055(2) 0.0492(19) 0.0088(16) 0.0202(16) 0.0284(17)
N5 0.028(2) 0.014(2) 0.016(2) -0.0005(16) 0.0080(17) -0.0061(18)
C36 0.040(3) 0.017(3) 0.018(2) 0.000(2) 0.009(2) -0.009(2)
C37 0.076(4) 0.017(3) 0.026(3) 0.001(2) 0.013(3) -0.005(3)
C38 0.043(3) 0.049(4) 0.035(3) 0.006(3) 0.009(3) -0.024(3)
C39 0.022(3) 0.020(3) 0.022(3) 0.002(2) 0.010(2) 0.002(2)
O8 0.0295(19) 0.0166(18) 0.0206(17) 0.0006(14) 0.0086(14) -0.0037(14)
N7A 0.031(2) 0.023(2) 0.020(2) -0.0023(17) 0.0116(18) -0.0105(18)
C40 0.031(3) 0.019(3) 0.021(3) -0.005(2) 0.007(2) -0.007(2)
C41 0.044(3) 0.029(3) 0.022(3) -0.002(2) 0.011(2) 0.002(3)
C42 0.034(3) 0.045(3) 0.038(3) -0.012(3) 0.008(3) -0.009(3)
_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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 C4 1.515(7) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C4 1.527(7) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.504(7) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 O1 1.484(6) . ?
O1 C5 1.325(5) . ?
C5 O2 1.207(5) . ?
C5 C6 1.528(7) . ?
C6 N1 1.452(6) . ?
C6 C7 1.536(7) . ?
C6 H6 1.0000 . ?
C7 C8 1.527(8) . ?
C7 C9 1.534(7) . ?
C7 H7 1.0000 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
N1 C10 1.323(6) . ?
N1 H1 0.8800 . ?
C10 O3 1.236(5) . ?
C10 C11 1.544(6) . ?
C11 N2 1.469(5) . ?
C11 C12 1.556(6) . ?
C11 H11 1.0000 . ?
C12 C13 1.503(7) . ?
C12 C14 1.520(6) . ?
C12 H12 1.0000 . ?
C13 F6 1.333(6) . ?
C13 F4 1.335(5) . ?
C13 F5 1.338(5) . ?
C14 F2 1.327(6) . ?
C14 F3 1.335(7) . ?
C14 F1 1.337(6) . ?
N2 C18 1.374(5) . ?
N2 C15 1.507(6) . ?
C15 C17 1.512(7) . ?
C15 C16 1.529(7) . ?
C15 H15 1.0000 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 O4 1.261(5) . ?
C18 N3 1.348(5) . ?
N3 C19 1.464(5) . ?
N3 H3 0.82(5) . ?
C19 C20 1.512(6) . ?
C19 C21 1.518(6) . ?
C19 H19 1.0000 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C25 1.491(8) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C25 1.520(8) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C25 1.505(7) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 O5 1.494(6) . ?
O5 C26 1.342(5) . ?
C26 O6 1.203(6) . ?
C26 C27 1.524(7) . ?
C27 N4 1.456(5) . ?
C27 C28 1.526(7) . ?
C27 H27 1.0000 . ?
C28 C30 1.526(7) . ?
C28 C29 1.535(7) . ?
C28 H28 1.0000 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
N4 C31 1.325(6) . ?
N4 H4 0.8800 . ?
C31 O7 1.232(5) . ?
C31 C32 1.554(6) . ?
C32 N5 1.460(5) . ?
C32 C33 1.560(6) . ?
C32 H32 1.0000 . ?
C33 C34 1.507(7) . ?
C33 C35 1.522(6) . ?
C33 H33 1.0000 . ?
C34 F12 1.338(6) . ?
C34 F11 1.344(6) . ?
C34 F10 1.344(5) . ?
C35 F9 1.325(5) . ?
C35 F8 1.336(6) . ?
C35 F7 1.342(5) . ?
N5 C39 1.376(6) . ?
N5 C36 1.492(5) . ?
C36 C38 1.519(7) . ?
C36 C37 1.523(7) . ?
C36 H36 1.0000 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 O8 1.243(5) . ?
C39 N7A 1.350(5) . ?
N7A C40 1.459(6) . ?
N7A H7A 0.8800 . ?
C40 C42 1.514(7) . ?
C40 C41 1.516(6) . ?
C40 H40 1.0000 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 C1 H1A 109.5 . . ?
C4 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C4 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C4 C2 H2A 109.5 . . ?
C4 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C4 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O1 C4 C3 109.1(4) . . ?
O1 C4 C1 102.2(4) . . ?
C3 C4 C1 111.3(5) . . ?
O1 C4 C2 109.1(4) . . ?
C3 C4 C2 112.9(5) . . ?
C1 C4 C2 111.6(4) . . ?
C5 O1 C4 121.8(4) . . ?
O2 C5 O1 126.3(4) . . ?
O2 C5 C6 123.6(4) . . ?
O1 C5 C6 110.1(4) . . ?
N1 C6 C5 108.6(4) . . ?
N1 C6 C7 111.4(4) . . ?
C5 C6 C7 112.3(4) . . ?
N1 C6 H6 108.2 . . ?
C5 C6 H6 108.2 . . ?
C7 C6 H6 108.2 . . ?
C8 C7 C9 111.7(4) . . ?
C8 C7 C6 110.6(4) . . ?
C9 C7 C6 113.1(4) . . ?
C8 C7 H7 107.1 . . ?
C9 C7 H7 107.1 . . ?
C6 C7 H7 107.1 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C10 N1 C6 121.4(4) . . ?
C10 N1 H1 119.3 . . ?
C6 N1 H1 119.3 . . ?
O3 C10 N1 123.7(4) . . ?
O3 C10 C11 118.6(4) . . ?
N1 C10 C11 117.7(4) . . ?
N2 C11 C10 111.2(3) . . ?
N2 C11 C12 114.3(4) . . ?
C10 C11 C12 113.9(4) . . ?
N2 C11 H11 105.5 . . ?
C10 C11 H11 105.5 . . ?
C12 C11 H11 105.5 . . ?
C13 C12 C14 110.0(4) . . ?
C13 C12 C11 113.3(4) . . ?
C14 C12 C11 110.1(4) . . ?
C13 C12 H12 107.7 . . ?
C14 C12 H12 107.7 . . ?
C11 C12 H12 107.7 . . ?
F6 C13 F4 106.3(4) . . ?
F6 C13 F5 105.8(4) . . ?
F4 C13 F5 105.0(4) . . ?
F6 C13 C12 112.4(4) . . ?
F4 C13 C12 113.9(4) . . ?
F5 C13 C12 112.7(4) . . ?
F2 C14 F3 107.3(5) . . ?
F2 C14 F1 105.5(5) . . ?
F3 C14 F1 106.2(5) . . ?
F2 C14 C12 113.8(5) . . ?
F3 C14 C12 112.2(4) . . ?
F1 C14 C12 111.3(4) . . ?
C18 N2 C11 118.4(4) . . ?
C18 N2 C15 120.1(3) . . ?
C11 N2 C15 118.5(3) . . ?
N2 C15 C17 112.9(4) . . ?
N2 C15 C16 111.3(4) . . ?
C17 C15 C16 111.6(4) . . ?
N2 C15 H15 106.9 . . ?
C17 C15 H15 106.9 . . ?
C16 C15 H15 106.9 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O4 C18 N3 120.0(4) . . ?
O4 C18 N2 120.1(4) . . ?
N3 C18 N2 119.9(4) . . ?
C18 N3 C19 122.7(4) . . ?
C18 N3 H3 123.6(13) . . ?
C19 N3 H3 112.8(13) . . ?
N3 C19 C20 109.3(4) . . ?
N3 C19 C21 109.7(4) . . ?
C20 C19 C21 113.2(4) . . ?
N3 C19 H19 108.1 . . ?
C20 C19 H19 108.1 . . ?
C21 C19 H19 108.1 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C25 C22 H22A 109.5 . . ?
C25 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C25 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C25 C23 H23A 109.5 . . ?
C25 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C25 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 H24A 109.5 . . ?
C25 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C25 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 C25 O5 109.5(4) . . ?
C22 C25 C24 112.8(5) . . ?
O5 C25 C24 110.0(4) . . ?
C22 C25 C23 111.9(5) . . ?
O5 C25 C23 100.8(4) . . ?
C24 C25 C23 111.2(5) . . ?
C26 O5 C25 120.8(4) . . ?
O6 C26 O5 126.2(5) . . ?
O6 C26 C27 124.9(4) . . ?
O5 C26 C27 108.8(4) . . ?
N4 C27 C26 110.1(4) . . ?
N4 C27 C28 110.7(4) . . ?
C26 C27 C28 111.8(4) . . ?
N4 C27 H27 108.0 . . ?
C26 C27 H27 108.0 . . ?
C28 C27 H27 108.0 . . ?
C30 C28 C27 112.3(4) . . ?
C30 C28 C29 111.1(4) . . ?
C27 C28 C29 113.0(4) . . ?
C30 C28 H28 106.6 . . ?
C27 C28 H28 106.6 . . ?
C29 C28 H28 106.6 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C31 N4 C27 119.7(4) . . ?
C31 N4 H4 120.2 . . ?
C27 N4 H4 120.2 . . ?
O7 C31 N4 124.7(4) . . ?
O7 C31 C32 119.5(4) . . ?
N4 C31 C32 115.8(4) . . ?
N5 C32 C31 112.8(4) . . ?
N5 C32 C33 113.7(3) . . ?
C31 C32 C33 113.3(3) . . ?
N5 C32 H32 105.3 . . ?
C31 C32 H32 105.3 . . ?
C33 C32 H32 105.3 . . ?
C34 C33 C35 109.9(4) . . ?
C34 C33 C32 112.1(4) . . ?
C35 C33 C32 111.9(4) . . ?
C34 C33 H33 107.6 . . ?
C35 C33 H33 107.6 . . ?
C32 C33 H33 107.6 . . ?
F12 C34 F11 106.3(4) . . ?
F12 C34 F10 105.0(4) . . ?
F11 C34 F10 106.4(4) . . ?
F12 C34 C33 113.4(4) . . ?
F11 C34 C33 112.6(4) . . ?
F10 C34 C33 112.5(4) . . ?
F9 C35 F8 107.5(4) . . ?
F9 C35 F7 105.8(4) . . ?
F8 C35 F7 106.4(4) . . ?
F9 C35 C33 113.7(4) . . ?
F8 C35 C33 112.5(4) . . ?
F7 C35 C33 110.5(4) . . ?
C39 N5 C32 120.0(3) . . ?
C39 N5 C36 123.0(4) . . ?
C32 N5 C36 117.0(3) . . ?
N5 C36 C38 111.9(4) . . ?
N5 C36 C37 110.9(4) . . ?
C38 C36 C37 112.4(4) . . ?
N5 C36 H36 107.1 . . ?
C38 C36 H36 107.1 . . ?
C37 C36 H36 107.1 . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C36 C38 H38A 109.5 . . ?
C36 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C36 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
O8 C39 N7A 121.1(4) . . ?
O8 C39 N5 120.7(4) . . ?
N7A C39 N5 118.2(4) . . ?
C39 N7A C40 121.2(4) . . ?
C39 N7A H7A 119.4 . . ?
C40 N7A H7A 119.4 . . ?
N7A C40 C42 110.0(4) . . ?
N7A C40 C41 110.0(4) . . ?
C42 C40 C41 112.4(4) . . ?
N7A C40 H40 108.1 . . ?
C42 C40 H40 108.1 . . ?
C41 C40 H40 108.1 . . ?
C40 C41 H41A 109.5 . . ?
C40 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C40 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C40 C42 H42A 109.5 . . ?
C40 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C40 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 C4 O1 C5 -67.4(6) . . . . ?
C1 C4 O1 C5 174.7(4) . . . . ?
C2 C4 O1 C5 56.5(5) . . . . ?
C4 O1 C5 O2 4.7(7) . . . . ?
C4 O1 C5 C6 -176.0(4) . . . . ?
O2 C5 C6 N1 -40.2(6) . . . . ?
O1 C5 C6 N1 140.5(4) . . . . ?
O2 C5 C6 C7 83.4(6) . . . . ?
O1 C5 C6 C7 -95.9(5) . . . . ?
N1 C6 C7 C8 -171.3(4) . . . . ?
C5 C6 C7 C8 66.7(5) . . . . ?
N1 C6 C7 C9 62.6(5) . . . . ?
C5 C6 C7 C9 -59.4(6) . . . . ?
C5 C6 N1 C10 -75.8(5) . . . . ?
C7 C6 N1 C10 160.1(4) . . . . ?
C6 N1 C10 O3 -10.0(6) . . . . ?
C6 N1 C10 C11 168.8(4) . . . . ?
O3 C10 C11 N2 111.8(4) . . . . ?
N1 C10 C11 N2 -67.1(5) . . . . ?
O3 C10 C11 C12 -117.3(4) . . . . ?
N1 C10 C11 C12 63.8(5) . . . . ?
N2 C11 C12 C13 -51.4(5) . . . . ?
C10 C11 C12 C13 179.3(4) . . . . ?
N2 C11 C12 C14 -175.0(4) . . . . ?
C10 C11 C12 C14 55.6(5) . . . . ?
C14 C12 C13 F6 67.7(5) . . . . ?
C11 C12 C13 F6 -56.0(5) . . . . ?
C14 C12 C13 F4 -53.2(6) . . . . ?
C11 C12 C13 F4 -177.0(4) . . . . ?
C14 C12 C13 F5 -172.8(4) . . . . ?
C11 C12 C13 F5 63.5(6) . . . . ?
C13 C12 C14 F2 52.8(7) . . . . ?
C11 C12 C14 F2 178.3(5) . . . . ?
C13 C12 C14 F3 -69.3(6) . . . . ?
C11 C12 C14 F3 56.2(6) . . . . ?
C13 C12 C14 F1 171.8(5) . . . . ?
C11 C12 C14 F1 -62.7(6) . . . . ?
C10 C11 N2 C18 71.0(5) . . . . ?
C12 C11 N2 C18 -59.6(5) . . . . ?
C10 C11 N2 C15 -89.6(5) . . . . ?
C12 C11 N2 C15 139.7(4) . . . . ?
C18 N2 C15 C17 155.9(4) . . . . ?
C11 N2 C15 C17 -43.7(6) . . . . ?
C18 N2 C15 C16 -77.7(5) . . . . ?
C11 N2 C15 C16 82.6(5) . . . . ?
C11 N2 C18 O4 11.9(6) . . . . ?
C15 N2 C18 O4 172.2(4) . . . . ?
C11 N2 C18 N3 -167.4(4) . . . . ?
C15 N2 C18 N3 -7.0(6) . . . . ?
O4 C18 N3 C19 -2.2(6) . . . . ?
N2 C18 N3 C19 177.0(4) . . . . ?
C18 N3 C19 C20 -116.4(4) . . . . ?
C18 N3 C19 C21 118.9(4) . . . . ?
C22 C25 O5 C26 -59.9(6) . . . . ?
C24 C25 O5 C26 64.6(6) . . . . ?
C23 C25 O5 C26 -177.9(4) . . . . ?
C25 O5 C26 O6 -2.0(7) . . . . ?
C25 O5 C26 C27 176.1(4) . . . . ?
O6 C26 C27 N4 -23.5(6) . . . . ?
O5 C26 C27 N4 158.3(3) . . . . ?
O6 C26 C27 C28 100.0(5) . . . . ?
O5 C26 C27 C28 -78.2(5) . . . . ?
N4 C27 C28 C30 -61.4(5) . . . . ?
C26 C27 C28 C30 175.4(4) . . . . ?
N4 C27 C28 C29 65.3(5) . . . . ?
C26 C27 C28 C29 -57.9(5) . . . . ?
C26 C27 N4 C31 -63.2(5) . . . . ?
C28 C27 N4 C31 172.7(4) . . . . ?
C27 N4 C31 O7 -2.4(6) . . . . ?
C27 N4 C31 C32 176.3(4) . . . . ?
O7 C31 C32 N5 128.2(4) . . . . ?
N4 C31 C32 N5 -50.6(5) . . . . ?
O7 C31 C32 C33 -100.7(5) . . . . ?
N4 C31 C32 C33 80.5(5) . . . . ?
N5 C32 C33 C34 -61.0(5) . . . . ?
C31 C32 C33 C34 168.4(4) . . . . ?
N5 C32 C33 C35 175.0(4) . . . . ?
C31 C32 C33 C35 44.4(5) . . . . ?
C35 C33 C34 F12 -58.0(6) . . . . ?
C32 C33 C34 F12 176.9(4) . . . . ?
C35 C33 C34 F11 62.7(6) . . . . ?
C32 C33 C34 F11 -62.4(5) . . . . ?
C35 C33 C34 F10 -177.0(4) . . . . ?
C32 C33 C34 F10 57.9(5) . . . . ?
C34 C33 C35 F9 47.4(6) . . . . ?
C32 C33 C35 F9 172.6(4) . . . . ?
C34 C33 C35 F8 -75.1(5) . . . . ?
C32 C33 C35 F8 50.2(5) . . . . ?
C34 C33 C35 F7 166.2(4) . . . . ?
C32 C33 C35 F7 -68.6(5) . . . . ?
C31 C32 N5 C39 83.7(5) . . . . ?
C33 C32 N5 C39 -47.1(5) . . . . ?
C31 C32 N5 C36 -93.4(4) . . . . ?
C33 C32 N5 C36 135.7(4) . . . . ?
C39 N5 C36 C38 104.6(5) . . . . ?
C32 N5 C36 C38 -78.3(5) . . . . ?
C39 N5 C36 C37 -129.0(5) . . . . ?
C32 N5 C36 C37 48.1(5) . . . . ?
C32 N5 C39 O8 -14.2(6) . . . . ?
C36 N5 C39 O8 162.7(4) . . . . ?
C32 N5 C39 N7A 163.9(4) . . . . ?
C36 N5 C39 N7A -19.1(6) . . . . ?
O8 C39 N7A C40 -14.7(7) . . . . ?
N5 C39 N7A C40 167.2(4) . . . . ?
C39 N7A C40 C42 -86.7(5) . . . . ?
C39 N7A C40 C41 149.0(4) . . . . ?
_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.051