# Supplementary Material (ESI) for Perkin Transactions
# This journal is © The Royal Society of Chemistry 2002

data_GR238576X    

_database_code_CSD	177055


_audit_creation_method            SHELXL

_journal_coden_Cambridge      207

loop_
_publ_author_name		  
'R.M.Angel'
'K.Biggadike'
'R.M.Farrell'
'S.S.Flack'
'A.P.Hancock'
'W.R.Irving'
'S.M.Lynn' 
'P.A.Procopiou'

_publ_requested_journal       'Perkin Transactions 1'


_publ_contact_author_name     	'Dr P Procopiou'  
_publ_contact_author_address 
;
Enzyme Medicinal Chemistry 1
Glaxo Wellcome Research & Development
Medicines Research Centre
Gunnels Wood Road
Stevenage
Herts
SG1  2NY
UK
;


_publ_contact_author_email	  'PAP1746@GGR.CO.UK'


_publ_section_title		  
;
Novel Glucocorticoid antedrugs possessing a 21-(gamma-lactone) ring
;

_chemical_name_systematic 
; 
(4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-4b,12-difluoro-5-hydroxy-4a,6a,8,
8-tetramethyl-6b-({[(3S)-2-oxotetrahydro-3-furanyl]sulfanyl}acetyl)-4a,4b,5,6,
6a,6b,9a,10,10a,10b,11,12-dodecahydro-2H-naphtho[2',1':4,5]indeno[1,2-d][1,3]
dioxol-2-one
; 

_chemical_name_common             ? 
_chemical_formula_moiety          ? 
_chemical_formula_structural      ? 
_chemical_formula_analytical      ? 
_chemical_formula_sum             'C28 H34 F2 O7 S' 
_chemical_formula_weight          552.64 
_chemical_melting_point           ? 
_chemical_compound_source         ? 

loop_ 
_atom_type_symbol 
_atom_type_description 
_atom_type_scat_dispersion_real 
_atom_type_scat_dispersion_imag 
_atom_type_scat_source 
'C'  'C'   0.0181   0.0091 
'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'   0.0492   0.0322 
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
'F'  'F'   0.0727   0.0534 
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
'S'  'S'   0.3331   0.5567 
'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, y+1/2, -z+1/2' 
'x+1/2, -y+1/2, -z' 

_cell_length_a                    7.939(2) 
_cell_length_b                    14.627(3) 
_cell_length_c                    29.719(6) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      3451.0(12) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     19 
_cell_measurement_theta_min       8.44 
_cell_measurement_theta_max       46.76 

_exptl_crystal_description        rhomboid 
_exptl_crystal_preparation	  'iso-butyl methylketone'
_exptl_crystal_colour             colorless 
_exptl_crystal_size_max           0.5 
_exptl_crystal_size_mid           0.2 
_exptl_crystal_size_min           0.2 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.249 
_exptl_crystal_density_method     ? 
_exptl_crystal_F_000              1360 
_exptl_absorpt_coefficient_mu     1.316 
_exptl_absorpt_correction_type    none 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 

_exptl_special_details 
; 
? 
; 

_diffrn_ambient_temperature       293(2) 
_diffrn_radiation_wavelength      1.54178 
_diffrn_radiation_type            CuK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device        'Siemens P3' 
_diffrn_measurement_method        '\w scans' 
_diffrn_standards_number          3 
_diffrn_standards_interval_count  97 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         0 
_diffrn_reflns_number             2624 
_diffrn_reflns_av_R_equivalents   0.0000 
_diffrn_reflns_av_sigmaI/netI     0.0694 
_diffrn_reflns_limit_h_min        0 
_diffrn_reflns_limit_h_max        8 
_diffrn_reflns_limit_k_min        0 
_diffrn_reflns_limit_k_max        15 
_diffrn_reflns_limit_l_min        0 
_diffrn_reflns_limit_l_max        32 
_diffrn_reflns_theta_min          2.97 
_diffrn_reflns_theta_max          57.27 
_reflns_number_total              2624 
_reflns_number_observed           1781 
_reflns_observed_criterion        >2sigma(I) 

_computing_data_collection        'Siemens XSCANS' 
_computing_cell_refinement        'Siemens XSCANS' 
_computing_data_reduction         'Siemens SHELXTL' 
_computing_structure_solution     'SHELXS-86 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-93 (Sheldrick, 1993)' 
_computing_molecular_graphics     'Siemens SHELXTL' 
_computing_publication_material   'Siemens SHELXTL' 

_refine_special_details 
; 
Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ 
or flagged by the user for potential systematic errors.  Weighted R-factors 
wR and all goodnesses 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 observed criterion 
of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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.

Refinement of the steroid structure led to the discovery of extraneous peaks 
in the difference E-map.  These peaks, which represent partially disordered 
solvent molecules, were modelled by the atoms C53 to C57 and C61 to C63. 
; 

_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme 
'calc w=1/[\s^2^(Fo^2^)+(0.0978P)^2^+1.7470P] 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     ? 
_refine_ls_extinction_method      SHELXL 
_refine_ls_extinction_coef        0.0020(3) 
_refine_ls_extinction_expression 
'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' 
_refine_ls_abs_structure_details 
'Flack H D (1983), Acta Cryst. A39, 876-881' 
_refine_ls_abs_structure_Flack    -0.05(7) 
_refine_ls_number_reflns          2624 
_refine_ls_number_parameters      460 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1080 
_refine_ls_R_factor_obs           0.0684 
_refine_ls_wR_factor_all          0.1917 
_refine_ls_wR_factor_obs          0.1620 
_refine_ls_goodness_of_fit_all    1.040 
_refine_ls_goodness_of_fit_obs    1.116 
_refine_ls_restrained_S_all       1.040 
_refine_ls_restrained_S_obs       1.116 
_refine_ls_shift/esd_max          0.007 
_refine_ls_shift/esd_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_thermal_displace_type 
_atom_site_occupancy 
_atom_site_calc_flag 
_atom_site_refinement_flags 
_atom_site_disorder_group 
S1 S -0.8196(4) -0.9095(2) -0.01758(8) 0.0678(8) Uani 1 d . . 
C1 C -1.1208(12) -1.3135(7) -0.2564(3) 0.048(2) Uani 1 d . . 
H1 H -1.0132(107) -1.2973(49) -0.2567(24) 0.030(21) Uiso 1 d . . 
C2 C -1.1227(14) -1.4027(7) -0.2671(3) 0.055(2) Uani 1 d . . 
H2 H -1.0159(131) -1.4274(62) -0.2723(30) 0.063(29) Uiso 1 d . . 
O3 O -1.2809(10) -1.5377(4) -0.2749(2) 0.072(2) Uani 1 d . . 
C3 C -1.2777(12) -1.4546(6) -0.2662(3) 0.052(2) Uani 1 d . . 
C4 C -1.4298(12) -1.4060(7) -0.2534(3) 0.053(2) Uani 1 d . . 
H4 H -1.5312(12) -1.4378(7) -0.2532(3) 0.064 Uiso 1 calc R . 
C5 C -1.4309(11) -1.3173(7) -0.2418(3) 0.048(2) Uani 1 d . . 
F6 F -1.7247(6) -1.3246(4) -0.2276(2) 0.082(2) Uani 1 d . . 
C6 C -1.5850(11) -1.2660(7) -0.2280(3) 0.056(3) Uani 1 d . . 
H6 H -1.6336(101) -1.2191(47) -0.2483(22) 0.035(21) Uiso 1 d . . 
C7 C -1.5619(10) -1.2267(6) -0.1807(3) 0.052(2) Uani 1 d . . 
H7A H -1.6585(10) -1.1890(6) -0.1732(3) 0.062 Uiso 1 calc R . 
H7B H -1.5568(10) -1.2764(6) -0.1591(3) 0.062 Uiso 1 calc R . 
C8 C -1.4016(10) -1.1693(5) -0.1769(3) 0.042(2) Uani 1 d . . 
H8 H -1.4154(10) -1.1143(5) -0.1954(3) 0.051 Uiso 1 calc R . 
F9 F -1.2393(6) -1.3036(2) -0.16658(13) 0.0437(11) Uani 1 d . . 
C9 C -1.2434(10) -1.2218(5) -0.1936(2) 0.036(2) Uani 1 d . . 
C10 C -1.2683(11) -1.2604(5) -0.2430(3) 0.045(2) Uani 1 d . . 
O11 O -1.0459(9) -1.1089(4) -0.2174(2) 0.057(2) Uani 1 d . . 
H11A H -0.9246(141) -1.0825(63) -0.2174(30) 0.074(30) Uiso 1 d . . 
C11 C -1.0737(11) -1.1772(6) -0.1845(3) 0.042(2) Uani 1 d . . 
H11 H -0.9658(102) -1.2270(49) -0.1831(24) 0.042(22) Uiso 1 d . . 
C12 C -1.0577(11) -1.1387(6) -0.1363(3) 0.042(2) Uani 1 d . . 
H12B H -1.0358(82) -1.1863(45) -0.1162(21) 0.018(18) Uiso 1 d . . 
H12A H -0.9368(99) -1.1040(47) -0.1390(22) 0.034(19) Uiso 1 d . . 
C13 C -1.2108(11) -1.0822(5) -0.1219(2) 0.041(2) Uani 1 d . . 
C14 C -1.3711(11) -1.1397(6) -0.1282(3) 0.046(2) Uani 1 d . . 
H14 H -1.3400(95) -1.1988(51) -0.1138(22) 0.034(20) Uiso 1 d . . 
C15 C -1.5086(12) -1.0833(6) -0.1038(3) 0.057(2) Uani 1 d . . 
H15A H -1.5426(12) -1.0306(6) -0.1214(3) 0.068 Uiso 1 calc R . 
H15B H -1.6068(12) -1.1203(6) -0.0970(3) 0.068 Uiso 1 calc R . 
O16 O -1.4469(9) -1.1220(5) -0.0269(2) 0.077(2) Uani 1 d . . 
C16 C -1.4152(12) -1.0548(6) -0.0608(3) 0.054(2) Uani 1 d . . 
H16 H -1.5023(104) -0.9905(56) -0.0448(27) 0.057(25) Uiso 1 d . . 
O17 O -1.1724(8) -1.1413(4) -0.0451(2) 0.053(2) Uani 1 d . . 
C17 C -1.2252(12) -1.0615(5) -0.0696(3) 0.047(2) Uani 1 d . . 
C18 C -1.2175(13) -0.9892(5) -0.1466(3) 0.054(2) Uani 1 d . . 
H18A H -1.2261(83) -0.9994(5) -0.1785(3) 0.081 Uiso 1 calc R . 
H18B H -1.1168(38) -0.9552(19) -0.1403(17) 0.081 Uiso 1 calc R . 
H18C H -1.3138(46) -0.9552(19) -0.1365(16) 0.081 Uiso 1 calc R . 
C19 C -1.2958(16) -1.1826(6) -0.2786(3) 0.070(3) Uani 1 d . . 
H19A H -1.3796(66) -1.1407(28) -0.2678(12) 0.105 Uiso 1 calc R . 
H19B H -1.3328(89) -1.2090(8) -0.3065(8) 0.105 Uiso 1 calc R . 
H19C H -1.1918(26) -1.1506(31) -0.2833(18) 0.105 Uiso 1 calc R . 
O20 O -1.1832(10) -0.9051(4) -0.0491(2) 0.075(2) Uani 1 d . . 
C20 C -1.1170(14) -0.9807(7) -0.0540(3) 0.059(3) Uani 1 d . . 
C21 C -0.9367(12) -0.9955(7) -0.0470(4) 0.062(3) Uani 1 d . . 
H21A H -0.8849(12) -1.0038(7) -0.0763(4) 0.074 Uiso 1 calc R . 
H21B H -0.9235(12) -1.0526(7) -0.0307(4) 0.074 Uiso 1 calc R . 
C23 C -0.8147(14) -0.8159(6) -0.0565(3) 0.062(3) Uani 1 d . . 
H23 H -0.9336(102) -0.7994(47) -0.0631(22) 0.030(19) Uiso 1 d . . 
C24 C -0.7274(16) -0.8461(8) -0.1000(4) 0.075(3) Uani 1 d . . 
O24 O -0.7811(13) -0.8933(6) -0.1291(2) 0.108(3) Uani 1 d . . 
O25 O -0.5727(12) -0.8176(6) -0.1001(3) 0.097(3) Uani 1 d . . 
C26 C -0.5277(18) -0.7662(10) -0.0596(5) 0.107(5) Uani 1 d . . 
H26A H -0.4644(18) -0.7116(10) -0.0671(5) 0.129 Uiso 1 calc R . 
H26B H -0.4614(18) -0.8034(10) -0.0392(5) 0.129 Uiso 1 calc R . 
C27 C -0.6976(16) -0.7418(7) -0.0389(4) 0.087(4) Uani 1 d . . 
H27A H -0.6920(16) -0.7429(7) -0.0063(4) 0.105 Uiso 1 calc R . 
H27B H -0.7345(16) -0.6817(7) -0.0486(4) 0.105 Uiso 1 calc R . 
C28 C -1.2955(13) -1.1544(8) -0.0100(3) 0.071(3) Uani 1 d . . 
C29 C -1.3068(16) -1.2557(9) -0.0017(5) 0.099(4) Uani 1 d . . 
H29A H -1.3912(93) -1.2677(11) 0.0207(26) 0.148 Uiso 1 calc R . 
H29B H -1.1999(41) -1.2780(15) 0.0086(33) 0.148 Uiso 1 calc R . 
H29C H -1.3366(127) -1.2862(12) -0.0292(10) 0.148 Uiso 1 calc R . 
C30 C -1.2401(17) -1.0995(10) 0.0324(3) 0.116(5) Uani 1 d . . 
H30A H -1.1198(22) -1.1025(59) 0.0355(20) 0.174 Uiso 1 calc R . 
H30B H -1.2920(106) -1.1254(46) 0.0587(5) 0.174 Uiso 1 calc R . 
H30C H -1.2742(115) -1.0369(19) 0.0293(16) 0.174 Uiso 1 calc R . 
C53 C -1.8706(35) -1.5990(15) -0.1088(7) 0.180(11) Uani 1 d . . 
C54 C -2.3944(47) -1.5421(33) -0.1297(15) 0.345(29) Uani 1 d . . 
C55 C -2.1384(66) -1.4943(33) -0.1059(20) 0.402(36) Uani 1 d . . 
C57 C -2.1715(91) -1.5443(46) -0.1398(16) 0.403(50) Uani 1 d . . 
C56 C -1.8346(53) -1.4693(16) -0.1555(8) 0.262(19) Uani 1 d . . 
C61 C -2.2046(61) -1.6771(48) -0.1550(11) 0.327(31) Uani 1 d . . 
C62 C -2.1817(103) -1.6235(65) -0.1246(28) 0.561(81) Uani 1 d . . 
C63 C -1.9243(39) -1.5349(18) -0.1293(8) 0.168(9) Uani 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 
S1 0.074(2) 0.070(2) 0.0595(14) -0.0092(13) -0.0099(14) -0.011(2) 
C1 0.033(5) 0.061(6) 0.048(5) -0.012(5) 0.008(4) -0.001(5) 
C2 0.059(7) 0.064(7) 0.040(5) -0.019(5) -0.003(4) 0.008(6) 
O3 0.074(5) 0.046(4) 0.095(5) -0.026(3) -0.002(4) 0.009(4) 
C3 0.045(6) 0.055(6) 0.057(5) -0.011(4) 0.001(5) 0.003(5) 
C4 0.043(5) 0.054(6) 0.062(5) -0.009(5) -0.001(5) -0.003(5) 
C5 0.039(5) 0.055(6) 0.050(5) -0.002(4) -0.007(4) -0.003(5) 
F6 0.026(3) 0.093(4) 0.126(5) -0.038(4) -0.005(3) -0.003(3) 
C6 0.028(5) 0.067(6) 0.074(6) -0.009(5) -0.017(5) 0.000(5) 
C7 0.027(4) 0.053(5) 0.077(6) -0.016(5) 0.000(5) 0.003(4) 
C8 0.032(4) 0.039(5) 0.055(5) 0.002(4) 0.000(4) 0.006(4) 
F9 0.046(3) 0.036(2) 0.049(2) 0.007(2) 0.000(2) 0.004(2) 
C9 0.034(5) 0.041(4) 0.032(4) 0.004(3) -0.003(4) 0.004(4) 
C10 0.041(5) 0.040(4) 0.053(5) -0.001(4) 0.002(4) -0.005(4) 
O11 0.067(4) 0.052(4) 0.053(3) 0.012(3) 0.004(3) -0.018(4) 
C11 0.037(4) 0.048(5) 0.041(5) -0.005(4) 0.002(4) -0.001(5) 
C12 0.037(5) 0.045(5) 0.044(5) -0.002(4) 0.003(4) 0.008(5) 
C13 0.042(5) 0.038(4) 0.043(4) -0.007(4) 0.001(4) 0.002(4) 
C14 0.038(5) 0.042(5) 0.059(5) -0.002(5) 0.008(4) -0.001(4) 
C15 0.042(5) 0.053(5) 0.075(6) -0.003(5) 0.007(5) 0.012(5) 
O16 0.049(4) 0.096(5) 0.084(5) 0.015(4) 0.020(4) 0.001(4) 
C16 0.047(6) 0.061(6) 0.053(5) -0.002(5) 0.009(5) 0.005(5) 
O17 0.048(4) 0.061(4) 0.050(3) -0.001(3) 0.012(3) -0.005(3) 
C17 0.043(5) 0.041(5) 0.055(5) -0.008(4) 0.002(4) 0.002(4) 
C18 0.064(6) 0.035(4) 0.063(5) -0.005(4) -0.006(5) 0.002(5) 
C19 0.098(8) 0.066(6) 0.046(5) 0.013(5) -0.018(6) -0.014(7) 
O20 0.071(5) 0.059(4) 0.096(5) -0.035(4) -0.006(4) 0.008(4) 
C20 0.074(7) 0.052(6) 0.052(5) -0.019(5) 0.011(5) -0.005(6) 
C21 0.040(5) 0.055(6) 0.091(7) -0.018(5) -0.011(5) 0.004(5) 
C23 0.056(7) 0.055(6) 0.074(6) -0.008(5) -0.008(6) 0.005(5) 
C24 0.079(9) 0.079(7) 0.066(7) 0.007(6) -0.005(6) 0.009(7) 
O24 0.141(8) 0.127(7) 0.057(4) -0.032(5) -0.015(5) -0.018(7) 
O25 0.084(6) 0.121(6) 0.086(5) -0.031(5) 0.012(5) -0.015(6) 
C26 0.093(10) 0.111(10) 0.119(11) -0.034(9) -0.012(9) -0.025(9) 
C27 0.092(9) 0.062(6) 0.107(8) -0.026(6) 0.005(8) 0.001(7) 
C28 0.051(6) 0.100(8) 0.060(6) 0.003(6) 0.016(5) -0.007(6) 
C29 0.067(8) 0.112(9) 0.117(8) 0.057(7) 0.008(8) -0.003(8) 
C30 0.085(9) 0.207(14) 0.056(6) -0.035(8) 0.012(6) 0.005(12) 
C53 0.201(25) 0.163(17) 0.177(19) 0.089(16) -0.012(17) 0.026(18) 
C54 0.173(27) 0.460(63) 0.401(56) 0.196(50) 0.023(37) 0.050(41) 
C55 0.318(56) 0.398(58) 0.490(73) 0.237(58) -0.232(57) -0.186(52) 
C57 0.455(97) 0.483(88) 0.270(44) -0.180(55) -0.224(58) 0.235(76) 
C56 0.452(59) 0.165(19) 0.168(19) 0.030(16) 0.002(29) -0.049(31) 
C61 0.199(33) 0.594(86) 0.188(24) -0.119(36) 0.032(24) -0.089(46) 
C62 0.494(114) 0.713(175) 0.477(106) 0.119(113) 0.192(102) -0.393(116) 
C63 0.213(28) 0.156(20) 0.136(17) -0.040(16) 0.014(19) -0.061(21) 

_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 
S1 C21 1.792(9) . ? 
S1 C23 1.792(10) . ? 
C1 C2 1.342(13) . ? 
C1 C10 1.461(12) . ? 
C2 C3 1.446(14) . ? 
O3 C3 1.243(10) . ? 
C3 C4 1.452(13) . ? 
C4 C5 1.343(12) . ? 
C5 C6 1.493(13) . ? 
C5 C10 1.536(12) . ? 
F6 C6 1.402(10) . ? 
C6 C7 1.531(13) . ? 
C7 C8 1.529(12) . ? 
C8 C14 1.530(12) . ? 
C8 C9 1.554(11) . ? 
F9 C9 1.443(8) . ? 
C9 C11 1.521(11) . ? 
C9 C10 1.584(11) . ? 
C10 C19 1.570(11) . ? 
O11 C11 1.415(10) . ? 
C11 C12 1.544(11) . ? 
C12 C13 1.531(11) . ? 
C13 C14 1.537(12) . ? 
C13 C18 1.547(11) . ? 
C13 C17 1.589(11) . ? 
C14 C15 1.548(12) . ? 
C15 C16 1.536(13) . ? 
O16 C28 1.386(12) . ? 
O16 C16 1.430(11) . ? 
C16 C17 1.534(13) . ? 
O17 C17 1.438(10) . ? 
O17 C28 1.442(11) . ? 
C17 C20 1.533(12) . ? 
O20 C20 1.233(11) . ? 
C20 C21 1.462(14) . ? 
C23 C27 1.521(15) . ? 
C23 C24 1.53(2) . ? 
C24 O24 1.184(13) . ? 
C24 O25 1.298(14) . ? 
O25 C26 1.465(14) . ? 
C26 C27 1.52(2) . ? 
C28 C29 1.51(2) . ? 
C28 C30 1.558(14) . ? 
C53 C63 1.20(3) . ? 
C54 C57 1.79(8) . ? 
C54 C62 2.07(11) . ? 
C55 C57 1.27(6) . ? 
C55 C63 1.93(7) . ? 
C55 C62 2.00(12) . ? 
C57 C62 1.25(10) . ? 
C57 C63 1.99(7) . ? 
C57 C61 2.01(10) . ? 
C56 C63 1.43(3) . ? 
C61 C62 1.21(11) . ? 

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 
C21 S1 C23 103.5(5) . . ? 
C2 C1 C10 124.9(9) . . ? 
C1 C2 C3 121.1(10) . . ? 
O3 C3 C2 121.8(9) . . ? 
O3 C3 C4 121.1(9) . . ? 
C2 C3 C4 117.1(7) . . ? 
C5 C4 C3 123.1(9) . . ? 
C4 C5 C6 124.2(9) . . ? 
C4 C5 C10 120.8(9) . . ? 
C6 C5 C10 115.0(7) . . ? 
F6 C6 C5 110.1(7) . . ? 
F6 C6 C7 108.6(8) . . ? 
C5 C6 C7 110.1(8) . . ? 
C8 C7 C6 111.9(8) . . ? 
C7 C8 C14 110.8(7) . . ? 
C7 C8 C9 112.2(6) . . ? 
C14 C8 C9 108.3(6) . . ? 
F9 C9 C11 103.7(6) . . ? 
F9 C9 C8 104.5(6) . . ? 
C11 C9 C8 116.5(6) . . ? 
F9 C9 C10 102.9(5) . . ? 
C11 C9 C10 115.4(7) . . ? 
C8 C9 C10 111.8(6) . . ? 
C1 C10 C5 113.1(7) . . ? 
C1 C10 C19 108.2(8) . . ? 
C5 C10 C19 106.9(8) . . ? 
C1 C10 C9 110.0(7) . . ? 
C5 C10 C9 106.1(7) . . ? 
C19 C10 C9 112.6(6) . . ? 
O11 C11 C9 108.5(7) . . ? 
O11 C11 C12 111.8(7) . . ? 
C9 C11 C12 113.2(7) . . ? 
C13 C12 C11 113.0(7) . . ? 
C12 C13 C14 109.1(6) . . ? 
C12 C13 C18 111.7(7) . . ? 
C14 C13 C18 113.3(7) . . ? 
C12 C13 C17 115.7(7) . . ? 
C14 C13 C17 99.4(7) . . ? 
C18 C13 C17 107.2(6) . . ? 
C8 C14 C13 113.6(7) . . ? 
C8 C14 C15 118.9(8) . . ? 
C13 C14 C15 103.6(7) . . ? 
C16 C15 C14 101.2(7) . . ? 
C28 O16 C16 109.7(7) . . ? 
O16 C16 C17 104.4(7) . . ? 
O16 C16 C15 108.3(8) . . ? 
C17 C16 C15 108.3(7) . . ? 
C17 O17 C28 106.1(7) . . ? 
O17 C17 C16 104.6(7) . . ? 
O17 C17 C20 108.0(7) . . ? 
C16 C17 C20 116.7(8) . . ? 
O17 C17 C13 108.7(6) . . ? 
C16 C17 C13 104.5(7) . . ? 
C20 C17 C13 113.7(7) . . ? 
O20 C20 C21 122.3(9) . . ? 
O20 C20 C17 119.2(9) . . ? 
C21 C20 C17 118.5(9) . . ? 
C20 C21 S1 118.2(7) . . ? 
C27 C23 C24 102.6(9) . . ? 
C27 C23 S1 109.7(7) . . ? 
C24 C23 S1 109.5(7) . . ? 
O24 C24 O25 121.8(12) . . ? 
O24 C24 C23 128.4(12) . . ? 
O25 C24 C23 109.7(10) . . ? 
C24 O25 C26 113.2(10) . . ? 
O25 C26 C27 103.7(10) . . ? 
C23 C27 C26 103.6(8) . . ? 
O16 C28 O17 106.3(7) . . ? 
O16 C28 C29 110.1(9) . . ? 
O17 C28 C29 106.8(9) . . ? 
O16 C28 C30 111.3(10) . . ? 
O17 C28 C30 109.0(8) . . ? 
C29 C28 C30 113.1(11) . . ? 
C57 C54 C62 36.7(28) . . ? 
C57 C55 C63 73.7(56) . . ? 
C57 C55 C62 37.0(42) . . ? 
C63 C55 C62 76.2(35) . . ? 
C62 C57 C55 105.0(68) . . ? 
C62 C57 C54 83.8(76) . . ? 
C55 C57 C54 93.4(53) . . ? 
C62 C57 C63 94.1(53) . . ? 
C55 C57 C63 68.4(46) . . ? 
C54 C57 C63 160.6(29) . . ? 
C62 C57 C61 34.5(54) . . ? 
C55 C57 C61 139.3(56) . . ? 
C54 C57 C61 85.8(42) . . ? 
C63 C57 C61 103.4(28) . . ? 
C62 C61 C57 35.6(49) . . ? 
C57 C62 C61 109.9(86) . . ? 
C57 C62 C55 38.0(38) . . ? 
C61 C62 C55 147.8(77) . . ? 
C57 C62 C54 59.5(65) . . ? 
C61 C62 C54 101.2(86) . . ? 
C55 C62 C54 67.5(43) . . ? 
C53 C63 C56 128.8(35) . . ? 
C53 C63 C55 111.8(26) . . ? 
C56 C63 C55 115.5(27) . . ? 
C53 C63 C57 112.1(31) . . ? 
C56 C63 C57 116.9(35) . . ? 
C55 C63 C57 37.9(19) . . ? 

_refine_diff_density_max    0.232 
_refine_diff_density_min   -0.218 
_refine_diff_density_rms    0.050