# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_r131219d1
_database_code_depnum_ccdc_archive 'CCDC 1007200'
_audit_update_record             
;
2014-06-07 deposited with the CCDC.
2015-04-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H25 F O2'
_chemical_formula_weight         268.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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   P2(1)2(1)2(1)

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                   5.9958(12)
_cell_length_b                   13.644(3)
_cell_length_c                   17.789(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1455.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4498
_cell_measurement_theta_min      1.8797
_cell_measurement_theta_max      27.9304

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9828
_exptl_absorpt_correction_T_max  0.9896
_exptl_absorpt_process_details   crystalclear

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  confocal
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            17044
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_sigmaI/netI    0.0332
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.88
_diffrn_reflns_theta_max         27.98
_reflns_number_total             3480
_reflns_number_gt                3288
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.1038P)²+0.3211P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.063(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.0(12)
_refine_ls_number_reflns         3480
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_ref         0.1600
_refine_ls_wR_factor_gt          0.1577
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.003
_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
F1 F 0.9019(4) 0.16910(12) 0.58630(8) 0.0602(5) Uani 1 1 d . . .
O1 O 0.6716(3) 0.12668(11) 0.19597(8) 0.0346(4) Uani 1 1 d . . .
O2 O 0.5472(3) 0.28008(13) 0.18326(10) 0.0502(5) Uani 1 1 d . . .
C1 C 0.9864(4) 0.11545(14) 0.52509(11) 0.0330(4) Uani 1 1 d . . .
H1 H 1.1528 0.1198 0.5248 0.040 Uiso 1 1 calc R . .
C2 C 0.8948(4) 0.16010(14) 0.45301(10) 0.0285(4) Uani 1 1 d . . .
H2A H 0.9516 0.2279 0.4478 0.034 Uiso 1 1 calc R . .
H2B H 0.7302 0.1633 0.4562 0.034 Uiso 1 1 calc R . .
C3 C 0.9616(3) 0.10051(12) 0.38286(10) 0.0217(4) Uani 1 1 d . . .
C4 C 0.8138(3) 0.13353(12) 0.31664(10) 0.0225(4) Uani 1 1 d . . .
H4 H 0.6588 0.1177 0.3335 0.027 Uiso 1 1 calc R . .
C5 C 0.7969(4) 0.23881(15) 0.28831(11) 0.0325(4) Uani 1 1 d . . .
H5A H 0.7189 0.2817 0.3247 0.039 Uiso 1 1 calc R . .
H5B H 0.9454 0.2667 0.2767 0.039 Uiso 1 1 calc R . .
C6 C 0.6591(4) 0.22255(15) 0.21737(11) 0.0342(5) Uani 1 1 d . . .
C7 C 0.8402(3) 0.07614(14) 0.24303(10) 0.0272(4) Uani 1 1 d . . .
C8 C 0.7782(4) -0.03000(15) 0.25731(11) 0.0315(4) Uani 1 1 d . . .
H8A H 0.8071 -0.0694 0.2116 0.038 Uiso 1 1 calc R . .
H8B H 0.6174 -0.0348 0.2694 0.038 Uiso 1 1 calc R . .
C9 C 0.9178(4) -0.07027(13) 0.32353(11) 0.0288(4) Uani 1 1 d . . .
H9A H 0.8715 -0.1386 0.3340 0.035 Uiso 1 1 calc R . .
H9B H 1.0770 -0.0714 0.3088 0.035 Uiso 1 1 calc R . .
C10 C 0.8919(3) -0.00918(12) 0.39564(10) 0.0221(4) Uani 1 1 d . . .
H10 H 0.7270 -0.0061 0.4038 0.026 Uiso 1 1 calc R . .
C11 C 0.9830(3) -0.05729(13) 0.46890(11) 0.0277(4) Uani 1 1 d . . .
C12 C 0.9170(4) 0.00973(15) 0.53537(11) 0.0331(4) Uani 1 1 d . . .
H12A H 0.7531 0.0070 0.5420 0.040 Uiso 1 1 calc R . .
H12B H 0.9863 -0.0159 0.5819 0.040 Uiso 1 1 calc R . .
C13 C 0.8677(4) -0.15674(16) 0.48097(14) 0.0405(5) Uani 1 1 d . . .
H13A H 0.9333 -0.2055 0.4471 0.061 Uiso 1 1 calc R . .
H13B H 0.7080 -0.1503 0.4703 0.061 Uiso 1 1 calc R . .
H13C H 0.8884 -0.1777 0.5332 0.061 Uiso 1 1 calc R . .
C14 C 1.2367(4) -0.07596(16) 0.46924(12) 0.0336(5) Uani 1 1 d . . .
H14A H 1.2757 -0.1172 0.5124 0.050 Uiso 1 1 calc R . .
H14B H 1.3158 -0.0133 0.4729 0.050 Uiso 1 1 calc R . .
H14C H 1.2798 -0.1093 0.4226 0.050 Uiso 1 1 calc R . .
C15 C 1.2121(3) 0.11722(15) 0.36635(12) 0.0297(4) Uani 1 1 d . . .
H15A H 1.2733 0.0596 0.3407 0.045 Uiso 1 1 calc R . .
H15B H 1.2921 0.1277 0.4137 0.045 Uiso 1 1 calc R . .
H15C H 1.2296 0.1750 0.3341 0.045 Uiso 1 1 calc R . .
C16 C 1.0589(4) 0.08472(18) 0.19916(12) 0.0384(5) Uani 1 1 d . . .
H16A H 1.0369 0.0604 0.1478 0.058 Uiso 1 1 calc R . .
H16B H 1.1745 0.0457 0.2241 0.058 Uiso 1 1 calc R . .
H16C H 1.1055 0.1535 0.1975 0.058 Uiso 1 1 calc R . .


_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 C1 1.406(2) . ?
O1 C6 1.364(3) . ?
O1 C7 1.483(2) . ?
O2 C6 1.198(3) . ?
C1 C12 1.512(3) . ?
C1 C2 1.522(3) . ?
C1 H1 1.0000 . ?
C2 C3 1.542(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.541(2) . ?
C3 C15 1.547(2) . ?
C3 C10 1.570(2) . ?
C4 C5 1.526(3) . ?
C4 C7 1.534(2) . ?
C4 H4 1.0000 . ?
C5 C6 1.525(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C7 C8 1.516(3) . ?
C7 C16 1.531(3) . ?
C8 C9 1.546(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.538(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.558(2) . ?
C10 H10 1.0000 . ?
C11 C13 1.538(3) . ?
C11 C14 1.542(3) . ?
C11 C12 1.546(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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 O1 C7 109.02(15) . . ?
F1 C1 C12 107.69(18) . . ?
F1 C1 C2 108.31(16) . . ?
C12 C1 C2 112.61(17) . . ?
F1 C1 H1 109.4 . . ?
C12 C1 H1 109.4 . . ?
C2 C1 H1 109.4 . . ?
C1 C2 C3 112.16(15) . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
C3 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C4 C3 C2 108.38(14) . . ?
C4 C3 C15 111.70(14) . . ?
C2 C3 C15 109.13(16) . . ?
C4 C3 C10 103.67(13) . . ?
C2 C3 C10 108.44(14) . . ?
C15 C3 C10 115.22(15) . . ?
C5 C4 C7 101.86(14) . . ?
C5 C4 C3 124.45(15) . . ?
C7 C4 C3 116.36(15) . . ?
C5 C4 H4 104.0 . . ?
C7 C4 H4 104.0 . . ?
C3 C4 H4 104.0 . . ?
C6 C5 C4 99.92(16) . . ?
C6 C5 H5A 111.8 . . ?
C4 C5 H5A 111.8 . . ?
C6 C5 H5B 111.8 . . ?
C4 C5 H5B 111.8 . . ?
H5A C5 H5B 109.5 . . ?
O2 C6 O1 121.2(2) . . ?
O2 C6 C5 128.9(2) . . ?
O1 C6 C5 109.92(16) . . ?
O1 C7 C8 111.83(16) . . ?
O1 C7 C16 105.11(15) . . ?
C8 C7 C16 111.61(17) . . ?
O1 C7 C4 100.04(14) . . ?
C8 C7 C4 108.61(15) . . ?
C16 C7 C4 118.98(17) . . ?
C7 C8 C9 109.55(16) . . ?
C7 C8 H8A 109.8 . . ?
C9 C8 H8A 109.8 . . ?
C7 C8 H8B 109.8 . . ?
C9 C8 H8B 109.8 . . ?
H8A C8 H8B 108.2 . . ?
C10 C9 C8 112.86(15) . . ?
C10 C9 H9A 109.0 . . ?
C8 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C8 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 C11 115.73(14) . . ?
C9 C10 C3 111.66(14) . . ?
C11 C10 C3 115.43(14) . . ?
C9 C10 H10 104.1 . . ?
C11 C10 H10 104.1 . . ?
C3 C10 H10 104.1 . . ?
C13 C11 C14 107.28(17) . . ?
C13 C11 C12 107.46(17) . . ?
C14 C11 C12 110.32(17) . . ?
C13 C11 C10 109.32(16) . . ?
C14 C11 C10 114.74(17) . . ?
C12 C11 C10 107.50(14) . . ?
C1 C12 C11 113.65(16) . . ?
C1 C12 H12A 108.8 . . ?
C11 C12 H12A 108.8 . . ?
C1 C12 H12B 108.8 . . ?
C11 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C3 C15 H15A 109.5 . . ?
C3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C7 C16 H16A 109.5 . . ?
C7 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C7 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
F1 C1 C2 C3 -174.93(17) . . . . ?
C12 C1 C2 C3 -55.9(2) . . . . ?
C1 C2 C3 C4 165.07(17) . . . . ?
C1 C2 C3 C15 -73.1(2) . . . . ?
C1 C2 C3 C10 53.1(2) . . . . ?
C2 C3 C4 C5 57.1(2) . . . . ?
C15 C3 C4 C5 -63.1(2) . . . . ?
C10 C3 C4 C5 172.21(16) . . . . ?
C2 C3 C4 C7 -174.69(15) . . . . ?
C15 C3 C4 C7 65.0(2) . . . . ?
C10 C3 C4 C7 -59.61(19) . . . . ?
C7 C4 C5 C6 37.94(18) . . . . ?
C3 C4 C5 C6 171.91(17) . . . . ?
C7 O1 C6 O2 173.8(2) . . . . ?
C7 O1 C6 C5 -8.0(2) . . . . ?
C4 C5 C6 O2 158.5(2) . . . . ?
C4 C5 C6 O1 -19.5(2) . . . . ?
C6 O1 C7 C8 146.77(17) . . . . ?
C6 O1 C7 C16 -91.96(18) . . . . ?
C6 O1 C7 C4 31.92(19) . . . . ?
C5 C4 C7 O1 -42.94(18) . . . . ?
C3 C4 C7 O1 178.54(14) . . . . ?
C5 C4 C7 C8 -160.21(16) . . . . ?
C3 C4 C7 C8 61.3(2) . . . . ?
C5 C4 C7 C16 70.7(2) . . . . ?
C3 C4 C7 C16 -67.8(2) . . . . ?
O1 C7 C8 C9 -163.84(15) . . . . ?
C16 C7 C8 C9 78.7(2) . . . . ?
C4 C7 C8 C9 -54.4(2) . . . . ?
C7 C8 C9 C10 56.2(2) . . . . ?
C8 C9 C10 C11 166.83(16) . . . . ?
C8 C9 C10 C3 -58.4(2) . . . . ?
C4 C3 C10 C9 55.73(18) . . . . ?
C2 C3 C10 C9 170.77(15) . . . . ?
C15 C3 C10 C9 -66.6(2) . . . . ?
C4 C3 C10 C11 -169.36(14) . . . . ?
C2 C3 C10 C11 -54.3(2) . . . . ?
C15 C3 C10 C11 68.3(2) . . . . ?
C9 C10 C11 C13 -57.2(2) . . . . ?
C3 C10 C11 C13 169.72(17) . . . . ?
C9 C10 C11 C14 63.3(2) . . . . ?
C3 C10 C11 C14 -69.7(2) . . . . ?
C9 C10 C11 C12 -173.58(16) . . . . ?
C3 C10 C11 C12 53.4(2) . . . . ?
F1 C1 C12 C11 175.62(17) . . . . ?
C2 C1 C12 C11 56.3(2) . . . . ?
C13 C11 C12 C1 -170.46(18) . . . . ?
C14 C11 C12 C1 72.9(2) . . . . ?
C10 C11 C12 C1 -52.9(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.98
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         1.024
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.052
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1007330'
_audit_update_record             
;
2014-06-09 deposited with the CCDC.
2015-04-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H31 F O8'
_chemical_formula_weight         466.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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                   8.7359(17)
_cell_length_b                   12.804(3)
_cell_length_c                   20.625(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2307.0(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    5522
_cell_measurement_theta_min      1.8721
_cell_measurement_theta_max      27.8664

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             992
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9793
_exptl_absorpt_correction_T_max  0.9875
_exptl_absorpt_process_details   crystalclear

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  confocal
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            22246
_diffrn_reflns_av_R_equivalents  0.1118
_diffrn_reflns_av_sigmaI/netI    0.0982
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         28.02
_reflns_number_total             5526
_reflns_number_gt                4090
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0517P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0128(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.7(10)
_refine_ls_number_reflns         5526
_refine_ls_number_parameters     304
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0615
_refine_ls_wR_factor_ref         0.1344
_refine_ls_wR_factor_gt          0.1225
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.1920(2) 0.42042(13) 1.02264(8) 0.0391(5) Uani 1 1 d . . .
O1 O -0.0492(2) 0.59610(16) 0.54309(9) 0.0332(5) Uani 1 1 d . . .
O2 O 0.0455(2) 0.54257(14) 0.63939(9) 0.0276(4) Uani 1 1 d . . .
O3 O 0.1516(3) 0.83502(16) 0.75705(10) 0.0404(6) Uani 1 1 d . . .
O4 O -0.0119(2) 0.72485(14) 0.80639(9) 0.0286(5) Uani 1 1 d . . .
O5 O 0.4251(2) 0.48636(15) 0.87087(9) 0.0299(5) Uani 1 1 d . . .
O6 O 0.3104(2) 0.39984(15) 0.78957(9) 0.0292(5) Uani 1 1 d . . .
O7 O 0.0268(2) 0.57128(16) 1.06735(9) 0.0308(5) Uani 1 1 d . . .
O8 O -0.0239(3) 0.74193(16) 1.05313(11) 0.0429(6) Uani 1 1 d . . .
C1 C 0.0305(4) 0.4177(2) 0.55825(14) 0.0320(7) Uani 1 1 d . . .
H1A H 0.0095 0.4092 0.5119 0.048 Uiso 1 1 calc R . .
H1B H -0.0377 0.3722 0.5832 0.048 Uiso 1 1 calc R . .
H1C H 0.1372 0.3989 0.5671 0.048 Uiso 1 1 calc R . .
C2 C 0.0040(3) 0.5276(2) 0.57708(13) 0.0266(6) Uani 1 1 d . . .
C3 C 0.0275(4) 0.6466(2) 0.66568(13) 0.0288(7) Uani 1 1 d . . .
H3 H 0.0588 0.6993 0.6325 0.035 Uiso 1 1 calc R . .
C4 C -0.1373(4) 0.6667(2) 0.68618(14) 0.0326(7) Uani 1 1 d . . .
H4A H -0.2064 0.6457 0.6504 0.039 Uiso 1 1 calc R . .
H4B H -0.1512 0.7425 0.6935 0.039 Uiso 1 1 calc R . .
C5 C -0.1837(3) 0.6077(2) 0.74798(13) 0.0292(6) Uani 1 1 d . . .
H5A H -0.2776 0.6393 0.7663 0.035 Uiso 1 1 calc R . .
H5B H -0.2062 0.5339 0.7372 0.035 Uiso 1 1 calc R . .
C6 C -0.0559(3) 0.6124(2) 0.79768(12) 0.0233(6) Uani 1 1 d . . .
C7 C 0.0923(3) 0.5662(2) 0.77215(12) 0.0228(6) Uani 1 1 d . . .
H7 H 0.0746 0.4972 0.7507 0.027 Uiso 1 1 calc R . .
C8 C 0.1412(3) 0.6493(2) 0.72320(13) 0.0269(6) Uani 1 1 d . . .
C9 C 0.0985(4) 0.7484(2) 0.76222(14) 0.0305(7) Uani 1 1 d . . .
C10 C 0.3060(4) 0.6488(2) 0.70067(13) 0.0327(7) Uani 1 1 d . . .
H10A H 0.3741 0.6496 0.7384 0.049 Uiso 1 1 calc R . .
H10B H 0.3254 0.7108 0.6740 0.049 Uiso 1 1 calc R . .
H10C H 0.3254 0.5859 0.6750 0.049 Uiso 1 1 calc R . .
C11 C 0.1921(3) 0.5549(2) 0.83319(12) 0.0217(6) Uani 1 1 d . . .
H11 H 0.2436 0.6234 0.8415 0.026 Uiso 1 1 calc R . .
C12 C 0.0789(3) 0.5330(2) 0.89055(12) 0.0217(6) Uani 1 1 d . . .
C13 C 0.1121(3) 0.5991(2) 0.95148(12) 0.0242(6) Uani 1 1 d . . .
H13A H 0.2199 0.5923 0.9657 0.029 Uiso 1 1 calc R . .
H13B H 0.0874 0.6737 0.9447 0.029 Uiso 1 1 calc R . .
C14 C 0.0016(3) 0.5472(2) 0.99905(12) 0.0250(6) Uani 1 1 d . . .
C15 C -0.1658(3) 0.5686(2) 0.97981(13) 0.0292(6) Uani 1 1 d . . .
H15A H -0.2131 0.6149 1.0126 0.035 Uiso 1 1 calc R . .
H15B H -0.2231 0.5019 0.9798 0.035 Uiso 1 1 calc R . .
C16 C -0.1803(3) 0.6199(2) 0.91246(13) 0.0278(6) Uani 1 1 d . . .
H16A H -0.2888 0.6192 0.8986 0.033 Uiso 1 1 calc R . .
H16B H -0.1464 0.6936 0.9149 0.033 Uiso 1 1 calc R . .
C17 C -0.0829(3) 0.5615(2) 0.86279(12) 0.0226(6) Uani 1 1 d . . .
H17 H -0.1363 0.4938 0.8540 0.027 Uiso 1 1 calc R . .
C18 C 0.3140(3) 0.4724(2) 0.82721(12) 0.0229(6) Uani 1 1 d . . .
C19 C 0.5380(3) 0.4035(2) 0.87355(15) 0.0354(7) Uani 1 1 d . . .
H19A H 0.4859 0.3358 0.8758 0.053 Uiso 1 1 calc R . .
H19B H 0.6022 0.4126 0.9121 0.053 Uiso 1 1 calc R . .
H19C H 0.6021 0.4061 0.8346 0.053 Uiso 1 1 calc R . .
C20 C 0.0766(3) 0.4200(2) 0.91877(12) 0.0240(6) Uani 1 1 d . . .
H20A H -0.0047 0.3780 0.8978 0.029 Uiso 1 1 calc R . .
H20B H 0.1762 0.3851 0.9114 0.029 Uiso 1 1 calc R . .
C21 C 0.0451(3) 0.4311(2) 0.99141(13) 0.0264(6) Uani 1 1 d . . .
C22 C -0.0544(4) 0.3489(2) 1.02226(15) 0.0421(8) Uani 1 1 d . . .
H22A H -0.0104 0.2797 1.0142 0.063 Uiso 1 1 calc R . .
H22B H -0.1575 0.3522 1.0036 0.063 Uiso 1 1 calc R . .
H22C H -0.0602 0.3612 1.0691 0.063 Uiso 1 1 calc R . .
C23 C 0.0081(4) 0.6695(3) 1.08875(14) 0.0333(7) Uani 1 1 d . . .
C24 C 0.0314(4) 0.6757(3) 1.16010(14) 0.0448(9) Uani 1 1 d . . .
H24A H 0.0255 0.7487 1.1740 0.067 Uiso 1 1 calc R . .
H24B H 0.1322 0.6473 1.1712 0.067 Uiso 1 1 calc R . .
H24C H -0.0482 0.6351 1.1821 0.067 Uiso 1 1 calc R . .


_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 C21 1.442(3) . ?
O1 C2 1.216(3) . ?
O2 C2 1.349(3) . ?
O2 C3 1.447(3) . ?
O3 C9 1.206(3) . ?
O4 C9 1.361(4) . ?
O4 C6 1.501(3) . ?
O5 C18 1.336(3) . ?
O5 C19 1.449(3) . ?
O6 C18 1.212(3) . ?
O7 C23 1.342(4) . ?
O7 C14 1.459(3) . ?
O8 C23 1.216(4) . ?
C1 C2 1.478(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C3 C4 1.522(4) . ?
C3 C8 1.547(4) . ?
C3 H3 1.0000 . ?
C4 C5 1.536(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.517(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C17 1.512(4) . ?
C6 C7 1.518(4) . ?
C7 C8 1.527(4) . ?
C7 C11 1.539(3) . ?
C7 H7 1.0000 . ?
C8 C10 1.513(4) . ?
C8 C9 1.549(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C18 1.504(4) . ?
C11 C12 1.568(4) . ?
C11 H11 1.0000 . ?
C12 C13 1.543(4) . ?
C12 C20 1.560(4) . ?
C12 C17 1.568(4) . ?
C13 C14 1.529(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.540(4) . ?
C14 C21 1.543(4) . ?
C15 C16 1.542(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.528(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17 1.0000 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.530(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.506(4) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.488(4) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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
C2 O2 C3 117.3(2) . . ?
C9 O4 C6 108.3(2) . . ?
C18 O5 C19 115.0(2) . . ?
C23 O7 C14 119.8(2) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 O2 123.3(3) . . ?
O1 C2 C1 126.5(3) . . ?
O2 C2 C1 110.1(2) . . ?
O2 C3 C4 111.2(2) . . ?
O2 C3 C8 103.7(2) . . ?
C4 C3 C8 113.0(2) . . ?
O2 C3 H3 109.6 . . ?
C4 C3 H3 109.6 . . ?
C8 C3 H3 109.6 . . ?
C3 C4 C5 113.4(2) . . ?
C3 C4 H4A 108.9 . . ?
C5 C4 H4A 108.9 . . ?
C3 C4 H4B 108.9 . . ?
C5 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
C6 C5 C4 110.3(2) . . ?
C6 C5 H5A 109.6 . . ?
C4 C5 H5A 109.6 . . ?
C6 C5 H5B 109.6 . . ?
C4 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
O4 C6 C17 110.3(2) . . ?
O4 C6 C5 107.9(2) . . ?
C17 C6 C5 117.9(2) . . ?
O4 C6 C7 101.3(2) . . ?
C17 C6 C7 105.8(2) . . ?
C5 C6 C7 112.2(2) . . ?
C6 C7 C8 101.3(2) . . ?
C6 C7 C11 103.7(2) . . ?
C8 C7 C11 116.6(2) . . ?
C6 C7 H7 111.5 . . ?
C8 C7 H7 111.5 . . ?
C11 C7 H7 111.5 . . ?
C10 C8 C7 117.8(2) . . ?
C10 C8 C3 112.0(2) . . ?
C7 C8 C3 108.2(2) . . ?
C10 C8 C9 113.0(3) . . ?
C7 C8 C9 99.2(2) . . ?
C3 C8 C9 105.2(2) . . ?
O3 C9 O4 122.4(3) . . ?
O3 C9 C8 128.0(3) . . ?
O4 C9 C8 109.7(2) . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C18 C11 C7 113.6(2) . . ?
C18 C11 C12 112.5(2) . . ?
C7 C11 C12 106.1(2) . . ?
C18 C11 H11 108.2 . . ?
C7 C11 H11 108.2 . . ?
C12 C11 H11 108.2 . . ?
C13 C12 C20 102.0(2) . . ?
C13 C12 C11 113.4(2) . . ?
C20 C12 C11 117.1(2) . . ?
C13 C12 C17 109.9(2) . . ?
C20 C12 C17 109.9(2) . . ?
C11 C12 C17 104.6(2) . . ?
C14 C13 C12 99.5(2) . . ?
C14 C13 H13A 111.9 . . ?
C12 C13 H13A 111.9 . . ?
C14 C13 H13B 111.9 . . ?
C12 C13 H13B 111.9 . . ?
H13A C13 H13B 109.6 . . ?
O7 C14 C13 115.6(2) . . ?
O7 C14 C15 110.8(2) . . ?
C13 C14 C15 110.9(2) . . ?
O7 C14 C21 105.3(2) . . ?
C13 C14 C21 101.4(2) . . ?
C15 C14 C21 112.3(2) . . ?
C14 C15 C16 112.7(2) . . ?
C14 C15 H15A 109.1 . . ?
C16 C15 H15A 109.1 . . ?
C14 C15 H15B 109.1 . . ?
C16 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
C17 C16 C15 110.5(2) . . ?
C17 C16 H16A 109.6 . . ?
C15 C16 H16A 109.6 . . ?
C17 C16 H16B 109.6 . . ?
C15 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
C6 C17 C16 118.1(2) . . ?
C6 C17 C12 106.5(2) . . ?
C16 C17 C12 111.8(2) . . ?
C6 C17 H17 106.6 . . ?
C16 C17 H17 106.6 . . ?
C12 C17 H17 106.6 . . ?
O6 C18 O5 123.6(3) . . ?
O6 C18 C11 124.9(2) . . ?
O5 C18 C11 111.4(2) . . ?
O5 C19 H19A 109.5 . . ?
O5 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O5 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C12 106.4(2) . . ?
C21 C20 H20A 110.5 . . ?
C12 C20 H20A 110.5 . . ?
C21 C20 H20B 110.5 . . ?
C12 C20 H20B 110.5 . . ?
H20A C20 H20B 108.6 . . ?
F1 C21 C22 105.0(2) . . ?
F1 C21 C20 105.6(2) . . ?
C22 C21 C20 116.9(2) . . ?
F1 C21 C14 105.4(2) . . ?
C22 C21 C14 119.2(2) . . ?
C20 C21 C14 103.5(2) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O8 C23 O7 123.0(3) . . ?
O8 C23 C24 126.0(3) . . ?
O7 C23 C24 111.0(3) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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 O2 C2 O1 -1.2(4) . . . . ?
C3 O2 C2 C1 179.8(2) . . . . ?
C2 O2 C3 C4 80.9(3) . . . . ?
C2 O2 C3 C8 -157.4(2) . . . . ?
O2 C3 C4 C5 72.5(3) . . . . ?
C8 C3 C4 C5 -43.7(3) . . . . ?
C3 C4 C5 C6 42.0(3) . . . . ?
C9 O4 C6 C17 141.0(2) . . . . ?
C9 O4 C6 C5 -88.8(3) . . . . ?
C9 O4 C6 C7 29.2(3) . . . . ?
C4 C5 C6 O4 52.2(3) . . . . ?
C4 C5 C6 C17 178.0(2) . . . . ?
C4 C5 C6 C7 -58.6(3) . . . . ?
O4 C6 C7 C8 -43.4(2) . . . . ?
C17 C6 C7 C8 -158.5(2) . . . . ?
C5 C6 C7 C8 71.5(3) . . . . ?
O4 C6 C7 C11 77.9(2) . . . . ?
C17 C6 C7 C11 -37.3(3) . . . . ?
C5 C6 C7 C11 -167.2(2) . . . . ?
C6 C7 C8 C10 162.7(2) . . . . ?
C11 C7 C8 C10 51.0(3) . . . . ?
C6 C7 C8 C3 -69.0(2) . . . . ?
C11 C7 C8 C3 179.3(2) . . . . ?
C6 C7 C8 C9 40.5(2) . . . . ?
C11 C7 C8 C9 -71.3(3) . . . . ?
O2 C3 C8 C10 69.8(3) . . . . ?
C4 C3 C8 C10 -169.6(2) . . . . ?
O2 C3 C8 C7 -61.7(3) . . . . ?
C4 C3 C8 C7 58.9(3) . . . . ?
O2 C3 C8 C9 -167.0(2) . . . . ?
C4 C3 C8 C9 -46.4(3) . . . . ?
C6 O4 C9 O3 177.6(3) . . . . ?
C6 O4 C9 C8 -3.0(3) . . . . ?
C10 C8 C9 O3 29.7(4) . . . . ?
C7 C8 C9 O3 155.3(3) . . . . ?
C3 C8 C9 O3 -92.8(4) . . . . ?
C10 C8 C9 O4 -149.6(2) . . . . ?
C7 C8 C9 O4 -24.0(3) . . . . ?
C3 C8 C9 O4 87.8(3) . . . . ?
C6 C7 C11 C18 155.6(2) . . . . ?
C8 C7 C11 C18 -94.0(3) . . . . ?
C6 C7 C11 C12 31.5(3) . . . . ?
C8 C7 C11 C12 141.9(2) . . . . ?
C18 C11 C12 C13 101.3(3) . . . . ?
C7 C11 C12 C13 -133.9(2) . . . . ?
C18 C11 C12 C20 -17.1(3) . . . . ?
C7 C11 C12 C20 107.7(2) . . . . ?
C18 C11 C12 C17 -139.0(2) . . . . ?
C7 C11 C12 C17 -14.2(3) . . . . ?
C20 C12 C13 C14 -44.8(2) . . . . ?
C11 C12 C13 C14 -171.6(2) . . . . ?
C17 C12 C13 C14 71.7(2) . . . . ?
C23 O7 C14 C13 64.8(3) . . . . ?
C23 O7 C14 C15 -62.6(3) . . . . ?
C23 O7 C14 C21 175.8(2) . . . . ?
C12 C13 C14 O7 165.1(2) . . . . ?
C12 C13 C14 C15 -67.6(3) . . . . ?
C12 C13 C14 C21 51.8(2) . . . . ?
O7 C14 C15 C16 139.5(2) . . . . ?
C13 C14 C15 C16 9.6(3) . . . . ?
C21 C14 C15 C16 -103.0(3) . . . . ?
C14 C15 C16 C17 48.0(3) . . . . ?
O4 C6 C17 C16 46.3(3) . . . . ?
C5 C6 C17 C16 -78.3(3) . . . . ?
C7 C6 C17 C16 155.2(2) . . . . ?
O4 C6 C17 C12 -80.4(3) . . . . ?
C5 C6 C17 C12 155.0(2) . . . . ?
C7 C6 C17 C12 28.5(3) . . . . ?
C15 C16 C17 C6 -167.5(2) . . . . ?
C15 C16 C17 C12 -43.4(3) . . . . ?
C13 C12 C17 C6 113.6(2) . . . . ?
C20 C12 C17 C6 -135.0(2) . . . . ?
C11 C12 C17 C6 -8.5(3) . . . . ?
C13 C12 C17 C16 -16.8(3) . . . . ?
C20 C12 C17 C16 94.6(3) . . . . ?
C11 C12 C17 C16 -138.8(2) . . . . ?
C19 O5 C18 O6 -4.2(4) . . . . ?
C19 O5 C18 C11 173.1(2) . . . . ?
C7 C11 C18 O6 -22.1(4) . . . . ?
C12 C11 C18 O6 98.4(3) . . . . ?
C7 C11 C18 O5 160.6(2) . . . . ?
C12 C11 C18 O5 -78.9(3) . . . . ?
C13 C12 C20 C21 21.5(3) . . . . ?
C11 C12 C20 C21 145.9(2) . . . . ?
C17 C12 C20 C21 -95.0(2) . . . . ?
C12 C20 C21 F1 -100.4(2) . . . . ?
C12 C20 C21 C22 143.3(3) . . . . ?
C12 C20 C21 C14 10.1(3) . . . . ?
O7 C14 C21 F1 -48.5(2) . . . . ?
C13 C14 C21 F1 72.3(2) . . . . ?
C15 C14 C21 F1 -169.2(2) . . . . ?
O7 C14 C21 C22 69.0(3) . . . . ?
C13 C14 C21 C22 -170.2(3) . . . . ?
C15 C14 C21 C22 -51.7(3) . . . . ?
O7 C14 C21 C20 -159.2(2) . . . . ?
C13 C14 C21 C20 -38.3(3) . . . . ?
C15 C14 C21 C20 80.1(3) . . . . ?
C14 O7 C23 O8 -2.9(5) . . . . ?
C14 O7 C23 C24 177.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        28.02
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.062
