# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2013

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#
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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
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data_shelxl
#TrackingRef 'cadgmf32.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H29 F6 N O3'
_chemical_formula_sum            'C28 H29 F6 N O3'
_chemical_formula_weight         541.52

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           orthorhombic
_symmetry_space_group_name_H-M   P212121

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

_cell_length_a                   5.9746(3)
_cell_length_b                   17.1181(11)
_cell_length_c                   25.5543(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2613.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    18245
_cell_measurement_theta_min      2.6685
_cell_measurement_theta_max      27.663

_exptl_crystal_description       prismatic
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1128
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9491
_exptl_absorpt_correction_T_max  0.9781
_exptl_absorpt_process_details   
;
SADABS-2004/1 - Bruker Nonius area detector scaling and absorption correction
;

_exptl_special_details           
;
SADABS-2004/1 - Bruker Nonius area detector scaling and absorption correction
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'TXS rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Kappa ApexII Ultra CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            43473
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_sigmaI/netI    0.1065
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.51
_diffrn_reflns_theta_max         27.77
_reflns_number_total             6160
_reflns_number_gt                5747
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^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       ?
_chemical_absolute_configuration syn
_refine_ls_number_reflns         6160
_refine_ls_number_parameters     448
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1247
_refine_ls_wR_factor_gt          0.1185
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.053
_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 -0.1495(4) 0.60341(9) 0.29802(5) 0.0804(6) Uani 1 1 d . . .
F2 F -0.1111(5) 0.53354(9) 0.36555(5) 0.1072(9) Uani 1 1 d U . .
F3 F 0.1586(5) 0.60307(13) 0.33917(9) 0.1088(8) Uani 1 1 d . . .
F4 F 0.0791(2) 0.09004(7) -0.05214(3) 0.0366(3) Uani 1 1 d . . .
F5 F 0.1202(2) 0.00780(6) 0.00966(4) 0.0397(3) Uani 1 1 d . . .
F6 F -0.1884(2) 0.06991(9) 0.00153(6) 0.0580(4) Uani 1 1 d . . .
O1 O 0.59846(19) 0.31766(7) 0.14216(4) 0.0214(3) Uani 1 1 d . . .
O21 O 0.7041(2) 0.19168(9) 0.27966(4) 0.0317(3) Uani 1 1 d . . .
O22 O 0.33961(19) 0.22066(7) 0.29247(4) 0.0203(3) Uani 1 1 d . . .
N2 N 0.6667(2) 0.27558(9) 0.18626(5) 0.0208(3) Uani 1 1 d . . .
C3 C 0.4961(3) 0.26216(9) 0.21502(5) 0.0177(3) Uani 1 1 d . . .
C4 C 0.2797(3) 0.29672(9) 0.19585(5) 0.0152(3) Uani 1 1 d . . .
C5 C 0.3542(3) 0.31686(9) 0.13928(5) 0.0167(3) Uani 1 1 d . . .
C6 C 0.2091(3) 0.36606(9) 0.22885(5) 0.0169(3) Uani 1 1 d . . .
C7 C 0.3341(4) 0.43456(11) 0.22980(6) 0.0288(4) Uani 1 1 d . . .
C8 C 0.0194(3) 0.35969(10) 0.25997(5) 0.0197(3) Uani 1 1 d . . .
C9 C 0.2653(4) 0.49683(12) 0.26063(7) 0.0388(5) Uani 1 1 d . . .
C10 C -0.0501(3) 0.42207(11) 0.29010(6) 0.0267(4) Uani 1 1 d . . .
C11 C 0.0734(4) 0.49070(11) 0.29032(6) 0.0331(5) Uani 1 1 d . . .
C12 C -0.0055(5) 0.55785(13) 0.32321(7) 0.0521(7) Uani 1 1 d . . .
C13 C 0.2792(3) 0.25671(10) 0.09974(5) 0.0167(3) Uani 1 1 d . . .
C14 C 0.0696(3) 0.26446(10) 0.07642(5) 0.0178(3) Uani 1 1 d . . .
C15 C 0.4116(3) 0.19174(10) 0.08789(5) 0.0185(3) Uani 1 1 d . . .
C16 C -0.0108(3) 0.20676(10) 0.04282(5) 0.0192(3) Uani 1 1 d . . .
C17 C 0.3330(3) 0.13446(10) 0.05471(5) 0.0203(3) Uani 1 1 d . . .
C18 C 0.1199(3) 0.14119(10) 0.03274(5) 0.0188(3) Uani 1 1 d . . .
C19 C 0.0329(3) 0.07779(10) -0.00162(6) 0.0238(3) Uani 1 1 d . . .
C20 C 0.5306(3) 0.22005(9) 0.26569(5) 0.0180(3) Uani 1 1 d . . .
C23 C 0.3326(3) 0.18353(10) 0.34429(6) 0.0208(3) Uani 1 1 d . . .
C24 C 0.2328(3) 0.24306(10) 0.38193(5) 0.0212(3) Uani 1 1 d . . .
C25 C 0.1937(3) 0.11009(10) 0.33897(6) 0.0228(3) Uani 1 1 d . . .
C26 C 0.1996(3) 0.20253(12) 0.43509(6) 0.0300(4) Uani 1 1 d . . .
C27 C 0.1577(3) 0.07024(11) 0.39200(6) 0.0254(4) Uani 1 1 d . . .
C28 C 0.0588(4) 0.12859(12) 0.43056(7) 0.0300(4) Uani 1 1 d . . .
C29 C 0.0118(4) -0.00212(13) 0.38582(8) 0.0372(4) Uani 1 1 d . . .
C30 C 0.3649(3) 0.32054(11) 0.38522(6) 0.0248(4) Uani 1 1 d . . .
C31 C 0.6062(3) 0.31039(14) 0.40394(8) 0.0330(4) Uani 1 1 d . . .
C32 C 0.2441(3) 0.38083(13) 0.41858(7) 0.0349(4) Uani 1 1 d . . .
H32A H 0.3234 0.4309 0.4165 0.052 Uiso 1 1 calc R . .
H32B H 0.2405 0.3631 0.4550 0.052 Uiso 1 1 calc R . .
H32C H 0.0908 0.3874 0.4057 0.052 Uiso 1 1 calc R . .
H4 H 0.169(3) 0.2592(12) 0.1976(6) 0.013(4) Uiso 1 1 d . . .
H5 H 0.314(4) 0.3743(13) 0.1277(7) 0.025(5) Uiso 1 1 d . . .
H7 H 0.465(4) 0.4403(14) 0.2097(8) 0.032(5) Uiso 1 1 d . . .
H8 H -0.065(4) 0.3124(13) 0.2609(7) 0.028(5) Uiso 1 1 d . . .
H9 H 0.335(4) 0.5425(16) 0.2589(8) 0.037(6) Uiso 1 1 d . . .
H10 H -0.182(4) 0.4149(13) 0.3112(8) 0.031(5) Uiso 1 1 d . . .
H23 H 0.486(4) 0.1729(13) 0.3545(7) 0.030(5) Uiso 1 1 d . . .
H24 H 0.071(3) 0.2558(11) 0.3702(6) 0.012(4) Uiso 1 1 d . . .
H27 H 0.305(4) 0.0543(13) 0.4045(8) 0.032(6) Uiso 1 1 d . . .
H30 H 0.373(4) 0.3453(14) 0.3493(8) 0.040(6) Uiso 1 1 d . . .
H14A H -0.020(3) 0.3103(12) 0.0838(6) 0.018(4) Uiso 1 1 d . . .
H15A H 0.560(3) 0.1910(13) 0.1031(7) 0.026(5) Uiso 1 1 d . . .
H16A H -0.152(4) 0.2096(11) 0.0267(7) 0.019(4) Uiso 1 1 d . . .
H17A H 0.436(3) 0.0881(12) 0.0476(6) 0.021(5) Uiso 1 1 d . . .
H25A H 0.049(4) 0.1195(12) 0.3211(7) 0.026(5) Uiso 1 1 d . . .
H26A H 0.355(4) 0.1894(15) 0.4482(8) 0.039(6) Uiso 1 1 d . . .
H28A H 0.033(3) 0.1033(10) 0.4651(6) 0.011(4) Uiso 1 1 d . . .
H29A H 0.000(3) -0.0265(12) 0.4196(7) 0.021(4) Uiso 1 1 d . . .
H31A H 0.687(3) 0.3582(12) 0.4060(6) 0.014(4) Uiso 1 1 d . . .
H25B H 0.269(4) 0.0738(16) 0.3165(9) 0.048(7) Uiso 1 1 d . . .
H26B H 0.120(3) 0.2387(12) 0.4602(7) 0.022(5) Uiso 1 1 d . . .
H28B H -0.070(5) 0.1422(16) 0.4183(9) 0.048(7) Uiso 1 1 d . . .
H29B H -0.136(5) 0.0162(16) 0.3718(9) 0.053(7) Uiso 1 1 d . . .
H31B H 0.604(4) 0.2843(15) 0.4421(8) 0.044(6) Uiso 1 1 d . . .
H29C H 0.081(4) -0.0374(15) 0.3610(8) 0.037(6) Uiso 1 1 d . . .
H31C H 0.697(4) 0.2819(16) 0.3835(10) 0.049(7) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.1463(18) 0.0454(9) 0.0495(7) -0.0108(6) 0.0024(9) 0.0556(11)
F2 0.238(3) 0.0401(9) 0.0434(7) -0.0030(6) 0.0602(12) 0.0396(13)
F3 0.139(2) 0.0728(14) 0.1152(14) -0.0763(12) -0.0193(14) 0.0090(13)
F4 0.0620(8) 0.0327(6) 0.0151(4) -0.0028(4) -0.0019(5) 0.0003(6)
F5 0.0693(9) 0.0192(5) 0.0306(5) 0.0003(4) -0.0120(5) -0.0019(6)
F6 0.0295(7) 0.0662(10) 0.0784(9) -0.0452(8) 0.0072(6) -0.0162(7)
O1 0.0182(5) 0.0295(6) 0.0164(5) 0.0044(4) 0.0005(4) -0.0038(5)
O21 0.0213(6) 0.0471(8) 0.0267(6) 0.0126(5) 0.0018(5) 0.0109(6)
O22 0.0178(5) 0.0285(6) 0.0146(4) 0.0064(4) 0.0014(4) 0.0032(5)
N2 0.0189(6) 0.0282(7) 0.0154(5) 0.0008(5) -0.0006(5) -0.0020(6)
C3 0.0177(7) 0.0201(8) 0.0152(6) -0.0005(5) 0.0000(5) -0.0008(6)
C4 0.0174(7) 0.0152(8) 0.0131(6) -0.0006(5) -0.0008(5) -0.0017(6)
C5 0.0159(7) 0.0186(7) 0.0156(6) 0.0017(6) 0.0016(5) 0.0006(6)
C6 0.0221(7) 0.0167(7) 0.0118(6) -0.0007(5) -0.0041(6) 0.0032(6)
C7 0.0414(10) 0.0224(9) 0.0226(7) 0.0008(6) 0.0044(8) -0.0068(8)
C8 0.0199(8) 0.0214(8) 0.0177(6) -0.0008(6) -0.0022(6) 0.0023(6)
C9 0.0723(16) 0.0155(9) 0.0287(8) -0.0017(7) 0.0015(9) -0.0101(10)
C10 0.0286(9) 0.0322(10) 0.0195(7) -0.0027(6) 0.0002(7) 0.0099(8)
C11 0.0575(13) 0.0216(9) 0.0203(7) -0.0025(6) -0.0022(8) 0.0120(9)
C12 0.105(2) 0.0272(10) 0.0238(8) -0.0047(7) 0.0054(12) 0.0159(13)
C13 0.0174(7) 0.0191(8) 0.0136(6) 0.0025(5) 0.0026(5) -0.0003(6)
C14 0.0162(7) 0.0219(8) 0.0154(6) 0.0000(5) 0.0024(5) 0.0041(6)
C15 0.0160(7) 0.0243(8) 0.0153(6) 0.0027(6) 0.0009(6) 0.0046(7)
C16 0.0156(7) 0.0267(8) 0.0152(6) 0.0005(6) 0.0004(6) 0.0006(6)
C17 0.0198(8) 0.0221(8) 0.0190(6) 0.0014(6) 0.0053(6) 0.0032(6)
C18 0.0214(8) 0.0225(8) 0.0124(6) 0.0005(5) 0.0029(6) -0.0026(6)
C19 0.0263(8) 0.0245(8) 0.0206(7) -0.0015(6) 0.0022(6) -0.0011(7)
C20 0.0172(7) 0.0194(8) 0.0173(6) -0.0007(6) -0.0007(6) 0.0029(6)
C23 0.0209(8) 0.0264(8) 0.0152(6) 0.0076(6) 0.0008(6) 0.0047(7)
C24 0.0192(8) 0.0272(9) 0.0172(6) 0.0043(6) 0.0004(6) 0.0019(7)
C25 0.0242(8) 0.0241(9) 0.0201(7) 0.0031(6) 0.0000(7) 0.0026(7)
C26 0.0379(10) 0.0347(10) 0.0175(7) 0.0043(7) 0.0055(7) -0.0010(9)
C27 0.0257(8) 0.0256(9) 0.0249(7) 0.0089(6) -0.0012(7) -0.0010(7)
C28 0.0322(10) 0.0330(10) 0.0248(8) 0.0097(7) 0.0086(7) -0.0008(8)
C29 0.0419(12) 0.0292(10) 0.0403(10) 0.0105(8) 0.0002(10) -0.0055(9)
C30 0.0232(8) 0.0294(9) 0.0218(7) 0.0012(6) -0.0019(6) -0.0023(7)
C31 0.0216(9) 0.0407(12) 0.0367(9) -0.0015(8) -0.0026(8) -0.0024(9)
C32 0.0324(10) 0.0355(11) 0.0367(9) -0.0073(8) -0.0030(8) -0.0021(9)

_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 C12 1.328(3) . ?
F2 C12 1.320(3) . ?
F3 C12 1.314(4) . ?
F4 C19 1.3368(17) . ?
F5 C19 1.338(2) . ?
F6 C19 1.331(2) . ?
O1 N2 1.3983(17) . ?
O1 C5 1.4615(19) . ?
O21 C20 1.1995(19) . ?
O22 C20 1.3304(18) . ?
O22 C23 1.4695(17) . ?
N2 C3 1.278(2) . ?
C3 C20 1.4962(19) . ?
C3 C4 1.504(2) . ?
C4 C6 1.516(2) . ?
C4 C5 1.5514(18) . ?
C5 C13 1.510(2) . ?
C6 C8 1.389(2) . ?
C6 C7 1.390(2) . ?
C7 C9 1.388(3) . ?
C8 C10 1.380(2) . ?
C9 C11 1.379(3) . ?
C10 C11 1.387(3) . ?
C11 C12 1.500(3) . ?
C13 C14 1.394(2) . ?
C13 C15 1.398(2) . ?
C14 C16 1.394(2) . ?
C15 C17 1.379(2) . ?
C16 C18 1.391(2) . ?
C17 C18 1.396(2) . ?
C18 C19 1.490(2) . ?
C23 C25 1.513(2) . ?
C23 C24 1.523(2) . ?
C24 C26 1.538(2) . ?
C24 C30 1.546(2) . ?
C25 C27 1.532(2) . ?
C26 C28 1.524(3) . ?
C27 C28 1.523(3) . ?
C27 C29 1.523(3) . ?
C30 C32 1.521(3) . ?
C30 C31 1.529(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
N2 O1 C5 109.09(10) . . ?
C20 O22 C23 118.98(11) . . ?
C3 N2 O1 108.87(12) . . ?
N2 C3 C20 118.33(14) . . ?
N2 C3 C4 115.34(12) . . ?
C20 C3 C4 126.14(13) . . ?
C3 C4 C6 111.47(11) . . ?
C3 C4 C5 98.30(11) . . ?
C6 C4 C5 115.09(12) . . ?
O1 C5 C13 109.63(12) . . ?
O1 C5 C4 103.98(11) . . ?
C13 C5 C4 112.76(12) . . ?
C8 C6 C7 119.62(15) . . ?
C8 C6 C4 118.95(14) . . ?
C7 C6 C4 121.40(14) . . ?
C9 C7 C6 119.94(18) . . ?
C10 C8 C6 120.28(16) . . ?
C11 C9 C7 120.00(19) . . ?
C8 C10 C11 119.82(17) . . ?
C9 C11 C10 120.30(16) . . ?
C9 C11 C12 120.8(2) . . ?
C10 C11 C12 119.0(2) . . ?
F3 C12 F2 106.7(2) . . ?
F3 C12 F1 106.7(2) . . ?
F2 C12 F1 105.8(3) . . ?
F3 C12 C11 113.0(2) . . ?
F2 C12 C11 111.59(18) . . ?
F1 C12 C11 112.46(16) . . ?
C14 C13 C15 119.46(14) . . ?
C14 C13 C5 119.18(14) . . ?
C15 C13 C5 121.30(13) . . ?
C13 C14 C16 120.36(14) . . ?
C17 C15 C13 120.40(14) . . ?
C18 C16 C14 119.50(15) . . ?
C15 C17 C18 119.97(15) . . ?
C16 C18 C17 120.26(14) . . ?
C16 C18 C19 120.06(14) . . ?
C17 C18 C19 119.68(15) . . ?
F6 C19 F4 106.21(14) . . ?
F6 C19 F5 106.45(16) . . ?
F4 C19 F5 105.56(13) . . ?
F6 C19 C18 112.62(14) . . ?
F4 C19 C18 112.51(14) . . ?
F5 C19 C18 112.93(13) . . ?
O21 C20 O22 126.27(13) . . ?
O21 C20 C3 124.87(13) . . ?
O22 C20 C3 108.86(12) . . ?
O22 C23 C25 107.10(12) . . ?
O22 C23 C24 106.92(13) . . ?
C25 C23 C24 113.46(14) . . ?
C23 C24 C26 107.85(14) . . ?
C23 C24 C30 114.12(13) . . ?
C26 C24 C30 113.89(13) . . ?
C23 C25 C27 111.56(13) . . ?
C28 C26 C24 112.26(14) . . ?
C28 C27 C29 112.25(16) . . ?
C28 C27 C25 109.56(15) . . ?
C29 C27 C25 110.53(15) . . ?
C27 C28 C26 112.32(15) . . ?
C32 C30 C31 110.43(16) . . ?
C32 C30 C24 111.77(14) . . ?
C31 C30 C24 113.63(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 O1 N2 C3 -11.74(17) . . . . ?
O1 N2 C3 C20 -177.85(12) . . . . ?
O1 N2 C3 C4 -2.55(18) . . . . ?
N2 C3 C4 C6 -106.89(15) . . . . ?
C20 C3 C4 C6 67.99(19) . . . . ?
N2 C3 C4 C5 14.30(17) . . . . ?
C20 C3 C4 C5 -170.82(14) . . . . ?
N2 O1 C5 C13 -100.66(13) . . . . ?
N2 O1 C5 C4 20.15(16) . . . . ?
C3 C4 C5 O1 -19.31(14) . . . . ?
C6 C4 C5 O1 99.16(14) . . . . ?
C3 C4 C5 C13 99.37(14) . . . . ?
C6 C4 C5 C13 -142.16(13) . . . . ?
C3 C4 C6 C8 -112.17(15) . . . . ?
C5 C4 C6 C8 137.02(13) . . . . ?
C3 C4 C6 C7 65.75(18) . . . . ?
C5 C4 C6 C7 -45.1(2) . . . . ?
C8 C6 C7 C9 -1.8(2) . . . . ?
C4 C6 C7 C9 -179.70(16) . . . . ?
C7 C6 C8 C10 2.6(2) . . . . ?
C4 C6 C8 C10 -179.45(14) . . . . ?
C6 C7 C9 C11 0.1(3) . . . . ?
C6 C8 C10 C11 -1.7(2) . . . . ?
C7 C9 C11 C10 0.9(3) . . . . ?
C7 C9 C11 C12 -179.02(19) . . . . ?
C8 C10 C11 C9 -0.1(3) . . . . ?
C8 C10 C11 C12 179.82(16) . . . . ?
C9 C11 C12 F3 -28.6(3) . . . . ?
C10 C11 C12 F3 151.5(2) . . . . ?
C9 C11 C12 F2 -148.9(2) . . . . ?
C10 C11 C12 F2 31.2(3) . . . . ?
C9 C11 C12 F1 92.3(3) . . . . ?
C10 C11 C12 F1 -87.6(3) . . . . ?
O1 C5 C13 C14 -156.58(12) . . . . ?
C4 C5 C13 C14 88.09(16) . . . . ?
O1 C5 C13 C15 26.33(18) . . . . ?
C4 C5 C13 C15 -89.00(17) . . . . ?
C15 C13 C14 C16 2.0(2) . . . . ?
C5 C13 C14 C16 -175.14(13) . . . . ?
C14 C13 C15 C17 -2.0(2) . . . . ?
C5 C13 C15 C17 175.03(14) . . . . ?
C13 C14 C16 C18 0.1(2) . . . . ?
C13 C15 C17 C18 0.0(2) . . . . ?
C14 C16 C18 C17 -2.1(2) . . . . ?
C14 C16 C18 C19 177.88(14) . . . . ?
C15 C17 C18 C16 2.1(2) . . . . ?
C15 C17 C18 C19 -177.91(14) . . . . ?
C16 C18 C19 F6 -31.7(2) . . . . ?
C17 C18 C19 F6 148.30(16) . . . . ?
C16 C18 C19 F4 88.29(18) . . . . ?
C17 C18 C19 F4 -91.69(18) . . . . ?
C16 C18 C19 F5 -152.33(14) . . . . ?
C17 C18 C19 F5 27.7(2) . . . . ?
C23 O22 C20 O21 -0.2(2) . . . . ?
C23 O22 C20 C3 -179.13(13) . . . . ?
N2 C3 C20 O21 -6.8(2) . . . . ?
C4 C3 C20 O21 178.51(16) . . . . ?
N2 C3 C20 O22 172.25(14) . . . . ?
C4 C3 C20 O22 -2.5(2) . . . . ?
C20 O22 C23 C25 -109.23(15) . . . . ?
C20 O22 C23 C24 128.84(14) . . . . ?
O22 C23 C24 C26 173.83(13) . . . . ?
C25 C23 C24 C26 55.99(17) . . . . ?
O22 C23 C24 C30 -58.55(17) . . . . ?
C25 C23 C24 C30 -176.39(13) . . . . ?
O22 C23 C25 C27 -174.95(13) . . . . ?
C24 C23 C25 C27 -57.22(18) . . . . ?
C23 C24 C26 C28 -55.1(2) . . . . ?
C30 C24 C26 C28 177.12(15) . . . . ?
C23 C25 C27 C28 54.1(2) . . . . ?
C23 C25 C27 C29 178.32(16) . . . . ?
C29 C27 C28 C26 -177.60(15) . . . . ?
C25 C27 C28 C26 -54.4(2) . . . . ?
C24 C26 C28 C27 56.7(2) . . . . ?
C23 C24 C30 C32 173.69(14) . . . . ?
C26 C24 C30 C32 -61.9(2) . . . . ?
C23 C24 C30 C31 -60.52(18) . . . . ?
C26 C24 C30 C31 63.93(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.77
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.039
_database_code_depnum_ccdc_archive 'CCDC 828351'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_shelxl2
#TrackingRef 'cadmefm_xp.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H47 N O5'
_chemical_formula_sum            'C32 H47 N O5'
_chemical_formula_weight         525.71

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21

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

_cell_length_a                   9.0578(3)
_cell_length_b                   17.9136(7)
_cell_length_c                   10.2169(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.597(2)
_cell_angle_gamma                90.00
_cell_volume                     1519.15(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    22357
_cell_measurement_theta_min      2.2720
_cell_measurement_theta_max      27.765

_exptl_crystal_description       prismatic
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             572
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9753
_exptl_absorpt_correction_T_max  0.9894
_exptl_absorpt_process_details   
;
SADABS-2004/1 - Bruker Nonius area detector scaling and absorption correction
;

_exptl_special_details           
;
SADABS-2004/1 - Bruker Nonius area detector scaling and absorption correction
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'TXS rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Kappa ApexII Ultra CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            42193
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0193
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         27.48
_reflns_number_total             6911
_reflns_number_gt                6435
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0727P)^2^+0.2728P] 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       ?
_chemical_absolute_configuration syn
_refine_ls_number_reflns         6911
_refine_ls_number_parameters     465
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1136
_refine_ls_wR_factor_gt          0.1096
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

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
O8 O 0.62748(14) 0.49265(7) 0.99655(11) 0.0290(3) Uani 1 1 d . . .
O7 O 0.82640(19) 0.40899(8) 1.03626(16) 0.0421(3) Uani 1 1 d . . .
O1 O 0.62045(15) 0.43199(8) 0.71107(14) 0.0363(3) Uani 1 1 d . . .
O21 O 1.09754(13) 0.56422(6) 0.85283(12) 0.0255(2) Uani 1 1 d . . .
O20 O 0.85409(15) 0.59084(7) 0.68216(13) 0.0329(3) Uani 1 1 d . . .
N2 N 0.70642(17) 0.39664(8) 0.64082(15) 0.0296(3) Uani 1 1 d . . .
C18 C 0.9691(2) 0.52827(13) 1.3415(2) 0.0412(4) Uani 1 1 d . . .
H18A H 1.0721 0.5491 1.3488 0.062 Uiso 1 1 calc R . .
H18B H 0.9550 0.4783 1.2990 0.062 Uiso 1 1 calc R . .
H18C H 0.9683 0.5249 1.4369 0.062 Uiso 1 1 calc R . .
C16 C 0.8320(2) 0.57874(10) 1.2476(2) 0.0334(4) Uani 1 1 d . . .
C14 C 0.6633(2) 0.54892(10) 1.22208(17) 0.0259(3) Uani 1 1 d . . .
C9 C 0.62006(19) 0.47725(9) 1.13485(16) 0.0243(3) Uani 1 1 d . . .
C6 C 0.7334(2) 0.45577(9) 0.96293(17) 0.0249(3) Uani 1 1 d . . .
C5 C 0.7273(2) 0.48195(9) 0.81893(18) 0.0267(3) Uani 1 1 d . . .
C4 C 0.89188(18) 0.47584(8) 0.81144(16) 0.0214(3) Uani 1 1 d . . .
C3 C 0.85244(19) 0.41912(8) 0.69143(16) 0.0226(3) Uani 1 1 d . . .
C32 C 0.96947(19) 0.38935(8) 0.63903(17) 0.0228(3) Uani 1 1 d . . .
C33 C 0.9185(2) 0.34995(10) 0.51106(19) 0.0283(3) Uani 1 1 d . . .
C35 C 1.0301(2) 0.32029(10) 0.46433(19) 0.0298(3) Uani 1 1 d . . .
C37 C 1.1946(2) 0.32855(9) 0.54346(19) 0.0272(3) Uani 1 1 d . . .
C38 C 1.3161(2) 0.29221(11) 0.4975(2) 0.0335(4) Uani 1 1 d . . .
H38A H 1.3566 0.2464 0.5529 0.050 Uiso 1 1 calc R . .
H38B H 1.4060 0.3266 0.5143 0.050 Uiso 1 1 calc R . .
H38C H 1.2649 0.2799 0.3957 0.050 Uiso 1 1 calc R . .
C17 C 0.8570(3) 0.65759(13) 1.3116(3) 0.0532(6) Uani 1 1 d . . .
H17A H 0.8631 0.6552 1.4095 0.080 Uiso 1 1 calc R . .
H17B H 0.7664 0.6894 1.2536 0.080 Uiso 1 1 calc R . .
H17C H 0.9574 0.6784 1.3125 0.080 Uiso 1 1 calc R . .
C10 C 0.4498(2) 0.45114(10) 1.10210(17) 0.0268(3) Uani 1 1 d . . .
C11 C 0.4191(2) 0.43974(10) 1.23739(18) 0.0281(3) Uani 1 1 d . . .
C15 C 0.2438(2) 0.41803(13) 1.1987(2) 0.0412(4) Uani 1 1 d . . .
H15A H 0.2271 0.4084 1.2862 0.062 Uiso 1 1 calc R . .
H15B H 0.2184 0.3729 1.1395 0.062 Uiso 1 1 calc R . .
H15C H 0.1733 0.4589 1.1455 0.062 Uiso 1 1 calc R . .
C12 C 0.4644(2) 0.51015(11) 1.32786(18) 0.0313(4) Uani 1 1 d . . .
C13 C 0.6354(2) 0.53555(11) 1.35925(18) 0.0304(4) Uani 1 1 d . . .
C36 C 1.2448(2) 0.36969(10) 0.6700(2) 0.0308(4) Uani 1 1 d . . .
C34 C 1.1339(2) 0.39955(9) 0.71781(19) 0.0280(3) Uani 1 1 d . . .
C19 C 0.94389(19) 0.55064(9) 0.77325(16) 0.0218(3) Uani 1 1 d . . .
C22 C 1.16574(19) 0.63307(9) 0.82252(19) 0.0266(3) Uani 1 1 d . . .
C27 C 1.2639(2) 0.67053(9) 0.9638(2) 0.0320(4) Uani 1 1 d . . .
C29 C 1.1664(3) 0.68542(10) 1.0561(2) 0.0378(4) Uani 1 1 d . . .
C31 C 1.0149(3) 0.73248(12) 0.9808(3) 0.0435(5) Uani 1 1 d . . .
C30 C 1.2737(4) 0.71965(14) 1.1992(3) 0.0582(6) Uani 1 1 d . . .
H30A H 1.2966 0.7718 1.1850 0.087 Uiso 1 1 calc R . .
H30B H 1.3750 0.6917 1.2402 0.087 Uiso 1 1 calc R . .
H30C H 1.2185 0.7175 1.2643 0.087 Uiso 1 1 calc R . .
C26 C 1.3437(3) 0.74031(11) 0.9312(3) 0.0431(5) Uani 1 1 d . . .
C25 C 1.4405(3) 0.72109(12) 0.8435(3) 0.0493(6) Uani 1 1 d . . .
C24 C 1.3400(2) 0.68152(11) 0.7041(3) 0.0416(5) Uani 1 1 d . . .
C23 C 1.2647(2) 0.61174(10) 0.7380(2) 0.0324(4) Uani 1 1 d . . .
C28 C 1.4356(3) 0.66304(15) 0.6143(3) 0.0589(7) Uani 1 1 d . . .
H28A H 1.4685 0.7094 0.5827 0.088 Uiso 1 1 calc R . .
H28B H 1.3681 0.6338 0.5307 0.088 Uiso 1 1 calc R . .
H28C H 1.5315 0.6341 0.6718 0.088 Uiso 1 1 calc R . .
H14 H 0.582(2) 0.5866(12) 1.164(2) 0.024(5) Uiso 1 1 d . . .
H10B H 0.371(2) 0.4873(12) 1.045(2) 0.024(5) Uiso 1 1 d . . .
H5 H 0.684(2) 0.5310(11) 0.798(2) 0.021(4) Uiso 1 1 d . . .
H12B H 0.389(3) 0.5531(15) 1.279(3) 0.042(6) Uiso 1 1 d . . .
H13A H 0.720(3) 0.4965(14) 1.420(2) 0.038(6) Uiso 1 1 d . . .
H23B H 1.348(3) 0.5780(13) 0.795(2) 0.033(5) Uiso 1 1 d . . .
H9 H 0.699(3) 0.4378(14) 1.183(3) 0.037(6) Uiso 1 1 d . . .
H38 H 0.994(3) 0.2953(13) 0.372(2) 0.030(5) Uiso 1 1 d . . .
H4 H 0.969(2) 0.4526(12) 0.893(2) 0.029(5) Uiso 1 1 d . . .
H36 H 1.360(3) 0.3794(14) 0.729(3) 0.041(6) Uiso 1 1 d . . .
H31A H 0.970(3) 0.7390(15) 1.052(3) 0.046(7) Uiso 1 1 d . . .
H34 H 1.172(3) 0.4289(13) 0.801(3) 0.033(5) Uiso 1 1 d . . .
H10A H 0.434(3) 0.4037(13) 1.052(2) 0.033(5) Uiso 1 1 d . . .
H27 H 1.357(3) 0.6348(14) 1.016(2) 0.035(6) Uiso 1 1 d . . .
H11 H 0.485(3) 0.4017(13) 1.291(2) 0.033(5) Uiso 1 1 d . . .
H22 H 1.077(3) 0.6628(12) 0.763(2) 0.030(5) Uiso 1 1 d . . .
H33 H 0.807(3) 0.3430(14) 0.457(3) 0.037(6) Uiso 1 1 d . . .
H26A H 1.407(3) 0.7591(16) 1.029(3) 0.051(7) Uiso 1 1 d . . .
H13B H 0.657(3) 0.5833(14) 1.408(3) 0.038(6) Uiso 1 1 d . . .
H24 H 1.253(3) 0.7124(14) 0.644(2) 0.034(5) Uiso 1 1 d . . .
H23A H 1.192(3) 0.5846(13) 0.643(2) 0.033(5) Uiso 1 1 d . . .
H29 H 1.138(3) 0.6361(13) 1.073(2) 0.030(5) Uiso 1 1 d . . .
H26B H 1.248(3) 0.7760(16) 0.870(3) 0.053(7) Uiso 1 1 d . . .
H16 H 0.836(3) 0.5802(13) 1.149(3) 0.038(6) Uiso 1 1 d . . .
H31C H 0.942(3) 0.7067(14) 0.892(3) 0.042(6) Uiso 1 1 d . . .
H25A H 1.534(3) 0.6909(16) 0.905(3) 0.050(7) Uiso 1 1 d . . .
H31B H 1.046(3) 0.7781(18) 0.959(3) 0.052(7) Uiso 1 1 d . . .
H12A H 0.455(3) 0.5008(14) 1.420(3) 0.041(6) Uiso 1 1 d . . .
H25B H 1.490(4) 0.7668(18) 0.825(3) 0.062(8) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O8 0.0299(6) 0.0397(7) 0.0193(5) 0.0050(5) 0.0119(5) 0.0123(5)
O7 0.0568(9) 0.0370(7) 0.0490(8) 0.0173(6) 0.0383(7) 0.0208(6)
O1 0.0242(6) 0.0530(8) 0.0355(7) -0.0071(6) 0.0160(5) -0.0074(5)
O21 0.0224(5) 0.0212(5) 0.0306(6) 0.0062(4) 0.0083(4) -0.0015(4)
O20 0.0301(6) 0.0307(6) 0.0287(6) 0.0074(5) 0.0022(5) -0.0041(5)
N2 0.0272(7) 0.0339(8) 0.0290(7) -0.0007(6) 0.0125(6) -0.0040(6)
C18 0.0243(8) 0.0507(11) 0.0414(10) -0.0028(9) 0.0057(8) -0.0035(8)
C16 0.0335(9) 0.0362(9) 0.0322(9) -0.0022(7) 0.0149(7) -0.0013(7)
C14 0.0260(7) 0.0283(8) 0.0236(7) 0.0018(6) 0.0101(6) 0.0047(6)
C9 0.0255(7) 0.0299(7) 0.0174(7) 0.0038(6) 0.0086(6) 0.0089(6)
C6 0.0300(8) 0.0210(7) 0.0289(8) 0.0018(6) 0.0173(6) 0.0001(6)
C5 0.0262(7) 0.0293(8) 0.0278(8) 0.0042(6) 0.0140(6) 0.0012(6)
C4 0.0235(7) 0.0223(7) 0.0205(7) 0.0008(6) 0.0110(6) -0.0009(6)
C3 0.0266(7) 0.0203(7) 0.0209(7) 0.0000(6) 0.0094(6) -0.0007(6)
C32 0.0229(7) 0.0196(7) 0.0266(7) -0.0004(6) 0.0106(6) -0.0024(5)
C33 0.0218(7) 0.0286(8) 0.0311(8) -0.0053(7) 0.0069(6) -0.0020(6)
C35 0.0298(8) 0.0293(8) 0.0308(9) -0.0066(7) 0.0127(7) 0.0009(7)
C37 0.0270(8) 0.0236(7) 0.0347(8) -0.0005(6) 0.0164(7) 0.0004(6)
C38 0.0306(8) 0.0334(9) 0.0426(10) -0.0017(8) 0.0211(8) 0.0033(7)
C17 0.0587(14) 0.0405(12) 0.0670(15) -0.0127(11) 0.0321(12) -0.0135(10)
C10 0.0270(8) 0.0308(8) 0.0214(7) 0.0010(6) 0.0084(6) 0.0042(6)
C11 0.0269(8) 0.0330(9) 0.0241(7) 0.0056(7) 0.0099(6) 0.0064(6)
C15 0.0323(9) 0.0528(12) 0.0404(10) 0.0071(9) 0.0164(8) -0.0012(8)
C12 0.0353(9) 0.0381(9) 0.0250(8) 0.0018(7) 0.0169(7) 0.0074(7)
C13 0.0333(8) 0.0372(9) 0.0213(7) -0.0035(7) 0.0115(7) 0.0031(7)
C36 0.0211(7) 0.0335(9) 0.0371(9) -0.0075(7) 0.0110(7) -0.0034(6)
C34 0.0242(8) 0.0290(8) 0.0292(8) -0.0063(7) 0.0091(6) -0.0035(6)
C19 0.0259(7) 0.0223(7) 0.0194(6) -0.0007(6) 0.0114(6) -0.0015(6)
C22 0.0212(7) 0.0207(7) 0.0362(9) 0.0106(6) 0.0097(6) 0.0014(6)
C27 0.0252(8) 0.0208(7) 0.0429(10) 0.0029(7) 0.0062(7) -0.0017(6)
C29 0.0482(11) 0.0229(8) 0.0398(10) -0.0012(7) 0.0149(9) -0.0035(7)
C31 0.0432(11) 0.0328(10) 0.0593(14) 0.0007(9) 0.0256(10) 0.0002(8)
C30 0.0792(18) 0.0394(11) 0.0437(12) -0.0078(9) 0.0117(12) -0.0012(11)
C26 0.0368(10) 0.0262(9) 0.0606(13) 0.0021(9) 0.0135(10) -0.0078(8)
C25 0.0297(10) 0.0337(10) 0.0857(17) 0.0144(10) 0.0243(11) -0.0041(8)
C24 0.0309(9) 0.0349(9) 0.0653(13) 0.0210(9) 0.0260(9) 0.0069(7)
C23 0.0298(8) 0.0281(8) 0.0410(10) 0.0113(7) 0.0158(8) 0.0031(7)
C28 0.0518(13) 0.0553(14) 0.0900(19) 0.0292(13) 0.0498(14) 0.0132(11)

_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
O8 C6 1.318(2) . ?
O8 C9 1.4674(18) . ?
O7 C6 1.212(2) . ?
O1 N2 1.404(2) . ?
O1 C5 1.449(2) . ?
O21 C19 1.3233(19) . ?
O21 C22 1.4668(19) . ?
O20 C19 1.200(2) . ?
N2 C3 1.277(2) . ?
C18 C16 1.525(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C16 C17 1.535(3) . ?
C16 C14 1.539(2) . ?
C16 H16 1.03(2) . ?
C14 C9 1.522(2) . ?
C14 C13 1.539(2) . ?
C14 H14 1.00(2) . ?
C9 C10 1.515(2) . ?
C9 H9 0.98(2) . ?
C6 C5 1.524(2) . ?
C5 C4 1.527(2) . ?
C5 H5 0.95(2) . ?
C4 C3 1.521(2) . ?
C4 C19 1.522(2) . ?
C4 H4 0.94(2) . ?
C3 C32 1.466(2) . ?
C32 C34 1.393(2) . ?
C32 C33 1.392(2) . ?
C33 C35 1.385(2) . ?
C33 H33 0.94(2) . ?
C35 C37 1.389(2) . ?
C35 H38 0.98(2) . ?
C37 C36 1.397(2) . ?
C37 C38 1.507(2) . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C10 C11 1.529(2) . ?
C10 H10B 0.97(2) . ?
C10 H10A 0.97(2) . ?
C11 C12 1.520(3) . ?
C11 C15 1.525(3) . ?
C11 H11 0.93(2) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C12 C13 1.520(3) . ?
C12 H12B 1.02(3) . ?
C12 H12A 0.99(2) . ?
C13 H13A 1.04(2) . ?
C13 H13B 0.97(3) . ?
C36 C34 1.388(2) . ?
C36 H36 0.99(2) . ?
C34 H34 0.94(2) . ?
C22 C27 1.516(3) . ?
C22 C23 1.522(3) . ?
C22 H22 0.95(2) . ?
C27 C26 1.545(2) . ?
C27 C29 1.551(3) . ?
C27 H27 1.02(2) . ?
C29 C30 1.523(3) . ?
C29 C31 1.530(3) . ?
C29 H29 0.96(2) . ?
C31 H31A 0.97(3) . ?
C31 H31C 1.00(3) . ?
C31 H31B 0.92(3) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C26 C25 1.523(4) . ?
C26 H26A 0.99(3) . ?
C26 H26B 1.06(3) . ?
C25 C24 1.523(4) . ?
C25 H25A 0.99(3) . ?
C25 H25B 0.99(3) . ?
C24 C28 1.529(3) . ?
C24 C23 1.529(2) . ?
C24 H24 0.96(2) . ?
C23 H23B 0.96(2) . ?
C23 H23A 1.05(2) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 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
C6 O8 C9 118.37(12) . . ?
N2 O1 C5 109.22(12) . . ?
C19 O21 C22 116.94(12) . . ?
C3 N2 O1 110.32(13) . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C18 C16 C17 109.50(18) . . ?
C18 C16 C14 113.85(16) . . ?
C17 C16 C14 111.04(16) . . ?
C18 C16 H16 107.2(13) . . ?
C17 C16 H16 109.8(14) . . ?
C14 C16 H16 105.2(13) . . ?
C9 C14 C16 113.43(13) . . ?
C9 C14 C13 107.71(14) . . ?
C16 C14 C13 114.42(14) . . ?
C9 C14 H14 105.6(12) . . ?
C16 C14 H14 108.1(12) . . ?
C13 C14 H14 107.1(12) . . ?
O8 C9 C10 106.28(12) . . ?
O8 C9 C14 107.75(13) . . ?
C10 C9 C14 112.98(13) . . ?
O8 C9 H9 108.2(14) . . ?
C10 C9 H9 111.0(14) . . ?
C14 C9 H9 110.4(14) . . ?
O7 C6 O8 125.72(15) . . ?
O7 C6 C5 123.85(15) . . ?
O8 C6 C5 110.40(14) . . ?
O1 C5 C6 107.40(13) . . ?
O1 C5 C4 106.62(13) . . ?
C6 C5 C4 111.58(13) . . ?
O1 C5 H5 108.0(12) . . ?
C6 C5 H5 110.8(11) . . ?
C4 C5 H5 112.1(12) . . ?
C3 C4 C19 112.23(12) . . ?
C3 C4 C5 99.75(12) . . ?
C19 C4 C5 111.00(13) . . ?
C3 C4 H4 105.6(13) . . ?
C19 C4 H4 114.8(13) . . ?
C5 C4 H4 112.4(13) . . ?
N2 C3 C32 121.36(14) . . ?
N2 C3 C4 114.09(14) . . ?
C32 C3 C4 124.52(13) . . ?
C34 C32 C33 119.03(14) . . ?
C34 C32 C3 120.24(14) . . ?
C33 C32 C3 120.73(14) . . ?
C35 C33 C32 120.32(15) . . ?
C35 C33 H33 120.4(15) . . ?
C32 C33 H33 119.2(15) . . ?
C33 C35 C37 121.27(16) . . ?
C33 C35 H38 119.9(12) . . ?
C37 C35 H38 118.8(12) . . ?
C35 C37 C36 118.09(15) . . ?
C35 C37 C38 121.32(16) . . ?
C36 C37 C38 120.56(15) . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C9 C10 C11 112.29(13) . . ?
C9 C10 H10B 111.5(12) . . ?
C11 C10 H10B 106.1(12) . . ?
C9 C10 H10A 107.9(13) . . ?
C11 C10 H10A 108.6(13) . . ?
H10B C10 H10A 110.5(18) . . ?
C12 C11 C15 111.65(15) . . ?
C12 C11 C10 109.65(14) . . ?
C15 C11 C10 110.32(14) . . ?
C12 C11 H11 107.4(14) . . ?
C15 C11 H11 108.9(14) . . ?
C10 C11 H11 108.8(14) . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C11 C12 C13 112.41(14) . . ?
C11 C12 H12B 111.2(14) . . ?
C13 C12 H12B 107.8(14) . . ?
C11 C12 H12A 109.4(15) . . ?
C13 C12 H12A 108.5(14) . . ?
H12B C12 H12A 107(2) . . ?
C12 C13 C14 112.30(14) . . ?
C12 C13 H13A 111.8(13) . . ?
C14 C13 H13A 107.0(13) . . ?
C12 C13 H13B 110.5(13) . . ?
C14 C13 H13B 105.0(14) . . ?
H13A C13 H13B 109.8(19) . . ?
C34 C36 C37 121.05(15) . . ?
C34 C36 H36 117.1(14) . . ?
C37 C36 H36 121.9(14) . . ?
C36 C34 C32 120.21(15) . . ?
C36 C34 H34 118.6(14) . . ?
C32 C34 H34 121.1(14) . . ?
O20 C19 O21 125.86(15) . . ?
O20 C19 C4 122.94(14) . . ?
O21 C19 C4 111.20(13) . . ?
O21 C22 C27 107.90(13) . . ?
O21 C22 C23 107.60(13) . . ?
C27 C22 C23 113.41(14) . . ?
O21 C22 H22 106.6(13) . . ?
C27 C22 H22 112.6(13) . . ?
C23 C22 H22 108.3(13) . . ?
C22 C27 C26 107.42(16) . . ?
C22 C27 C29 113.27(14) . . ?
C26 C27 C29 114.90(16) . . ?
C22 C27 H27 105.3(13) . . ?
C26 C27 H27 104.9(13) . . ?
C29 C27 H27 110.3(13) . . ?
C30 C29 C31 111.09(19) . . ?
C30 C29 C27 110.67(19) . . ?
C31 C29 C27 113.81(17) . . ?
C30 C29 H29 108.1(13) . . ?
C31 C29 H29 110.2(13) . . ?
C27 C29 H29 102.5(13) . . ?
C29 C31 H31A 104.3(15) . . ?
C29 C31 H31C 109.8(14) . . ?
H31A C31 H31C 114(2) . . ?
C29 C31 H31B 108.1(17) . . ?
H31A C31 H31B 109(2) . . ?
H31C C31 H31B 110(2) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C25 C26 C27 111.90(17) . . ?
C25 C26 H26A 115.9(16) . . ?
C27 C26 H26A 100.7(16) . . ?
C25 C26 H26B 108.7(15) . . ?
C27 C26 H26B 105.8(16) . . ?
H26A C26 H26B 113(2) . . ?
C26 C25 C24 112.72(17) . . ?
C26 C25 H25A 107.4(15) . . ?
C24 C25 H25A 112.3(16) . . ?
C26 C25 H25B 109.8(18) . . ?
C24 C25 H25B 110.6(18) . . ?
H25A C25 H25B 104(2) . . ?
C28 C24 C25 113.09(19) . . ?
C28 C24 C23 111.71(18) . . ?
C25 C24 C23 108.83(18) . . ?
C28 C24 H24 105.2(14) . . ?
C25 C24 H24 111.0(14) . . ?
C23 C24 H24 106.8(14) . . ?
C22 C23 C24 109.92(16) . . ?
C22 C23 H23B 108.0(13) . . ?
C24 C23 H23B 110.0(13) . . ?
C22 C23 H23A 110.1(12) . . ?
C24 C23 H23A 110.2(12) . . ?
H23B C23 H23A 108.7(18) . . ?
C24 C28 H28A 109.5 . . ?
C24 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C24 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.039





_database_code_depnum_ccdc_archive 'CCDC 828352'