data_pw13abs _audit_update_record ; 2018-02-01 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-cyano-1-methyl-3-(4-methoxyphenyl)-2-(2-phenylsulfonylethyl)piperidine ; _chemical_name_common ? _chemical_melting_point 411 _chemical_formula_moiety 'C22 H24 N2 O3 S' _chemical_formula_sum 'C22 H24 N2 O3 S' _chemical_formula_weight 396.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 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' 'N' 'N' 0.0311 0.0180 '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' 'S' 'S' 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.90480(10) _cell_length_b 11.17140(10) _cell_length_c 17.31320(10) _cell_angle_alpha 90.00 _cell_angle_beta 95.5410(10) _cell_angle_gamma 90.00 _cell_volume 2099.27(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 19818 _cell_measurement_theta_min 2.5820 _cell_measurement_theta_max 71.1490 _exptl_crystal_description 'paralellepiped, cut from longer' _exptl_crystal_colour 'colourless, transparent' _exptl_crystal_size_max 0.367 _exptl_crystal_size_mid 0.244 _exptl_crystal_size_min 0.185 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.255 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 1.567 _exptl_absorpt_correction_T_min 0.618 _exptl_absorpt_correction_T_max 0.777 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.25a (Rigaku Oxford Diffraction, 2015) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_measurement_method '\w scans' _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Cu) X-ray Source' _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Ruby' _diffrn_detector 'CCD plate' _diffrn_detector_type Ruby _diffrn_detector_area_resol_mean 10.4922 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 37267 _diffrn_reflns_av_R_equivalents 0.0367 _diffrn_reflns_av_sigmaI/netI 0.0145 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 4.60 _diffrn_reflns_theta_max 71.22 _reflns_number_total 4060 _reflns_number_gt 3618 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro 1.171.39.25a (Rigaku OD, 2015)' _computing_cell_refinement 'CrysAlisPro 1.171.39.25a (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.39.25a (Rigaku OD, 2015)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (Bruker AXS, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.0885P)^2^+0.3757P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4060 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0494 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_ref 0.1368 _refine_ls_wR_factor_gt 0.1302 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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 S1 S 0.44304(3) 0.01476(4) 0.13456(2) 0.04440(15) Uani 1 1 d . . . O1 O 0.40478(14) -0.03020(14) 0.20564(9) 0.0656(4) Uani 1 1 d . . . O2 O 0.42492(13) -0.05997(13) 0.06675(8) 0.0646(4) Uani 1 1 d . . . O3 O 0.61659(15) -0.18897(17) 0.52860(9) 0.0790(5) Uani 1 1 d . . . N1 N 0.86652(13) 0.05421(13) 0.14197(8) 0.0489(3) Uani 1 1 d . . . N2 N 0.93972(16) -0.22094(14) 0.21629(10) 0.0611(4) Uani 1 1 d . . . C2 C 0.81506(15) -0.01872(13) 0.20120(9) 0.0405(3) Uani 1 1 d . . . C3 C 0.82341(15) 0.04845(15) 0.28073(9) 0.0450(4) Uani 1 1 d . . . H3 H 0.7723 0.1203 0.2724 0.054 Uiso 1 1 calc R . . C4 C 0.95547(18) 0.09253(19) 0.30357(12) 0.0613(5) Uani 1 1 d . . . C5 C 0.9991(2) 0.1681(2) 0.23877(14) 0.0690(6) Uani 1 1 d . . . H5A H 0.9481 0.2390 0.2313 0.083 Uiso 1 1 calc R . . H5B H 1.0834 0.1935 0.2528 0.083 Uiso 1 1 calc R . . C6 C 0.99217(18) 0.09696(18) 0.16423(12) 0.0589(5) Uani 1 1 d . . . H6A H 1.0187 0.1468 0.1231 0.071 Uiso 1 1 calc R . . H6B H 1.0476 0.0290 0.1708 0.071 Uiso 1 1 calc R . . C7 C 0.8613(2) -0.0029(2) 0.06579(11) 0.0644(5) Uani 1 1 d . . . H7A H 0.8963 0.0496 0.0299 0.097 Uiso 1 1 calc R . . H7B H 0.7771 -0.0195 0.0476 0.097 Uiso 1 1 calc R . . H7C H 0.9071 -0.0765 0.0698 0.097 Uiso 1 1 calc R . . C8 C 0.88511(15) -0.13447(15) 0.21203(9) 0.0445(4) Uani 1 1 d . . . C9 C 0.67997(14) -0.05408(14) 0.17455(9) 0.0421(3) Uani 1 1 d . . . H9A H 0.6792 -0.1099 0.1316 0.050 Uiso 1 1 calc R . . H9B H 0.6445 -0.0942 0.2168 0.050 Uiso 1 1 calc R . . C10 C 0.60106(15) 0.05491(15) 0.14930(10) 0.0470(4) Uani 1 1 d . . . H10A H 0.6274 0.0872 0.1016 0.056 Uiso 1 1 calc R . . H10B H 0.6122 0.1165 0.1888 0.056 Uiso 1 1 calc R . . C11 C 0.36998(14) 0.15422(15) 0.11410(9) 0.0436(3) Uani 1 1 d . . . C12 C 0.37454(19) 0.20554(19) 0.04191(11) 0.0579(5) Uani 1 1 d . . . H12 H 0.4139 0.1667 0.0037 0.069 Uiso 1 1 calc R . . C13 C 0.3194(2) 0.3158(2) 0.02751(14) 0.0760(6) Uani 1 1 d . . . H13 H 0.3219 0.3519 -0.0207 0.091 Uiso 1 1 calc R . . C14 C 0.2610(2) 0.3721(2) 0.08411(16) 0.0772(7) Uani 1 1 d . . . H14 H 0.2225 0.4453 0.0735 0.093 Uiso 1 1 calc R . . C15 C 0.2586(2) 0.3217(2) 0.15614(15) 0.0721(6) Uani 1 1 d . . . H15 H 0.2201 0.3614 0.1944 0.086 Uiso 1 1 calc R . . C16 C 0.31380(17) 0.21140(18) 0.17194(11) 0.0565(4) Uani 1 1 d . . . H16 H 0.3130 0.1766 0.2207 0.068 Uiso 1 1 calc R . . C21 C 0.77081(16) -0.02163(15) 0.34513(9) 0.0449(4) Uani 1 1 d . . . C22 C 0.64948(17) -0.00389(17) 0.36096(10) 0.0522(4) Uani 1 1 d . . . H22 H 0.6001 0.0488 0.3302 0.063 Uiso 1 1 calc R . . C23 C 0.60037(18) -0.0622(2) 0.42105(11) 0.0592(5) Uani 1 1 d . . . H23 H 0.5185 -0.0496 0.4297 0.071 Uiso 1 1 calc R . . C24 C 0.67241(18) -0.13946(18) 0.46854(10) 0.0559(4) Uani 1 1 d . . . C25 C 0.79331(19) -0.15994(19) 0.45425(10) 0.0575(5) Uani 1 1 d . . . H25 H 0.8423 -0.2123 0.4855 0.069 Uiso 1 1 calc R . . C26 C 0.84099(17) -0.10169(18) 0.39279(10) 0.0534(4) Uani 1 1 d . . . H26 H 0.9220 -0.1165 0.3832 0.064 Uiso 1 1 calc R . . C27 C 0.6905(3) -0.2445(3) 0.58894(13) 0.0812(7) Uani 1 1 d . . . H27A H 0.6393 -0.2749 0.6266 0.122 Uiso 1 1 calc R . . H27B H 0.7476 -0.1873 0.6132 0.122 Uiso 1 1 calc R . . H27C H 0.7351 -0.3093 0.5684 0.122 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0381(2) 0.0450(2) 0.0500(3) 0.00387(15) 0.00398(16) -0.00111(14) O1 0.0575(8) 0.0696(9) 0.0719(9) 0.0241(7) 0.0173(6) 0.0027(6) O2 0.0607(8) 0.0584(8) 0.0732(8) -0.0156(7) -0.0017(6) -0.0027(6) O3 0.0731(10) 0.1041(12) 0.0625(8) 0.0215(8) 0.0202(7) 0.0110(9) N1 0.0441(8) 0.0483(8) 0.0554(8) 0.0081(6) 0.0100(6) 0.0009(6) N2 0.0639(10) 0.0483(9) 0.0708(10) 0.0028(7) 0.0053(8) 0.0133(7) C2 0.0388(8) 0.0370(8) 0.0457(8) 0.0022(6) 0.0044(6) 0.0033(6) C3 0.0410(8) 0.0422(8) 0.0517(9) -0.0041(7) 0.0038(6) 0.0024(6) C4 0.0518(10) 0.0675(12) 0.0641(11) -0.0111(9) 0.0037(8) -0.0155(9) C5 0.0600(12) 0.0580(11) 0.0903(15) -0.0091(10) 0.0147(10) -0.0178(9) C6 0.0498(10) 0.0558(10) 0.0733(11) 0.0045(9) 0.0167(8) -0.0064(8) C7 0.0637(13) 0.0820(14) 0.0492(10) 0.0074(9) 0.0137(9) -0.0015(10) C8 0.0436(8) 0.0425(9) 0.0474(8) -0.0004(6) 0.0043(6) 0.0021(7) C9 0.0403(8) 0.0399(8) 0.0455(8) 0.0022(6) 0.0011(6) 0.0000(6) C10 0.0391(8) 0.0442(8) 0.0569(9) 0.0068(7) 0.0004(7) -0.0003(6) C11 0.0345(7) 0.0481(8) 0.0471(8) 0.0021(6) -0.0009(6) -0.0006(6) C12 0.0597(11) 0.0657(11) 0.0476(9) 0.0054(8) 0.0015(8) 0.0060(9) C13 0.0765(14) 0.0770(15) 0.0737(13) 0.0292(11) 0.0034(11) 0.0118(12) C14 0.0615(13) 0.0583(12) 0.1125(19) 0.0197(12) 0.0119(12) 0.0142(10) C15 0.0586(12) 0.0637(13) 0.0968(16) -0.0053(11) 0.0220(11) 0.0120(10) C16 0.0481(10) 0.0642(11) 0.0584(10) 0.0017(8) 0.0118(8) 0.0063(8) C21 0.0433(9) 0.0478(9) 0.0431(8) -0.0063(6) 0.0019(6) 0.0030(7) C22 0.0453(9) 0.0618(11) 0.0489(9) 0.0010(7) 0.0018(7) 0.0082(7) C23 0.0441(9) 0.0800(13) 0.0543(9) 0.0020(9) 0.0083(7) 0.0064(9) C24 0.0595(11) 0.0638(11) 0.0452(9) -0.0006(8) 0.0093(7) 0.0024(9) C25 0.0610(11) 0.0621(11) 0.0491(9) 0.0042(8) 0.0040(8) 0.0159(9) C26 0.0479(9) 0.0610(11) 0.0514(9) -0.0003(8) 0.0056(7) 0.0113(8) C27 0.0962(18) 0.0913(17) 0.0571(11) 0.0203(11) 0.0117(11) 0.0073(14) _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 O1 1.4283(14) . ? S1 O2 1.4386(14) . ? S1 C11 1.7700(17) . ? S1 C10 1.7750(17) . ? O3 C24 1.371(2) . ? O3 C27 1.401(3) . ? N1 C7 1.462(2) . ? N1 C2 1.463(2) . ? N1 C6 1.467(2) . ? N2 C8 1.133(2) . ? C2 C8 1.504(2) . ? C2 C9 1.552(2) . ? C2 C3 1.563(2) . ? C3 C21 1.519(2) . ? C3 C4 1.537(2) . ? C3 H3 0.9800 . ? C4 C5 1.517(3) . ? C5 C6 1.511(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C9 C10 1.530(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C16 1.380(2) . ? C11 C12 1.380(2) . ? C12 C13 1.383(3) . ? C12 H12 0.9300 . ? C13 C14 1.372(4) . ? C13 H13 0.9300 . ? C14 C15 1.371(3) . ? C14 H14 0.9300 . ? C15 C16 1.386(3) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C21 C22 1.391(3) . ? C21 C26 1.394(2) . ? C22 C23 1.379(3) . ? C22 H22 0.9300 . ? C23 C24 1.383(3) . ? C23 H23 0.9300 . ? C24 C25 1.384(3) . ? C25 C26 1.390(3) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? 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 O1 S1 O2 118.07(10) . . ? O1 S1 C11 108.58(8) . . ? O2 S1 C11 108.89(8) . . ? O1 S1 C10 108.98(8) . . ? O2 S1 C10 108.60(9) . . ? C11 S1 C10 102.61(8) . . ? C24 O3 C27 118.60(18) . . ? C7 N1 C2 113.89(14) . . ? C7 N1 C6 109.47(15) . . ? C2 N1 C6 114.13(14) . . ? N1 C2 C8 109.96(13) . . ? N1 C2 C9 110.52(13) . . ? C8 C2 C9 105.92(13) . . ? N1 C2 C3 110.88(13) . . ? C8 C2 C3 108.50(13) . . ? C9 C2 C3 110.92(13) . . ? C21 C3 C4 112.77(14) . . ? C21 C3 C2 113.89(13) . . ? C4 C3 C2 110.72(14) . . ? C21 C3 H3 106.3 . . ? C4 C3 H3 106.3 . . ? C2 C3 H3 106.3 . . ? C5 C4 C3 109.94(16) . . ? C6 C5 C4 110.24(17) . . ? 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 . . ? N1 C6 C5 111.35(16) . . ? N1 C6 H6A 109.4 . . ? C5 C6 H6A 109.4 . . ? N1 C6 H6B 109.4 . . ? C5 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? N1 C7 H7A 109.5 . . ? N1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N2 C8 C2 176.33(18) . . ? C10 C9 C2 111.96(13) . . ? C10 C9 H9A 109.2 . . ? C2 C9 H9A 109.2 . . ? C10 C9 H9B 109.2 . . ? C2 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? C9 C10 S1 110.57(11) . . ? C9 C10 H10A 109.5 . . ? S1 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? S1 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? C16 C11 C12 121.48(17) . . ? C16 C11 S1 119.01(13) . . ? C12 C11 S1 119.47(14) . . ? C11 C12 C13 118.70(19) . . ? C11 C12 H12 120.7 . . ? C13 C12 H12 120.7 . . ? C14 C13 C12 120.2(2) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C15 C14 C13 120.8(2) . . ? C15 C14 H14 119.6 . . ? C13 C14 H14 119.6 . . ? C14 C15 C16 119.9(2) . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C11 C16 C15 118.85(19) . . ? C11 C16 H16 120.6 . . ? C15 C16 H16 120.6 . . ? C22 C21 C26 116.93(17) . . ? C22 C21 C3 120.32(15) . . ? C26 C21 C3 122.70(16) . . ? C23 C22 C21 121.83(17) . . ? C23 C22 H22 119.1 . . ? C21 C22 H22 119.1 . . ? C22 C23 C24 120.24(18) . . ? C22 C23 H23 119.9 . . ? C24 C23 H23 119.9 . . ? O3 C24 C23 115.73(17) . . ? O3 C24 C25 124.70(18) . . ? C23 C24 C25 119.55(17) . . ? C24 C25 C26 119.51(17) . . ? C24 C25 H25 120.2 . . ? C26 C25 H25 120.2 . . ? C25 C26 C21 121.92(17) . . ? C25 C26 H26 119.0 . . ? C21 C26 H26 119.0 . . ? O3 C27 H27A 109.5 . . ? O3 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? O3 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 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 C7 N1 C2 C8 60.26(19) . . . . ? C6 N1 C2 C8 -66.46(18) . . . . ? C7 N1 C2 C9 -56.33(18) . . . . ? C6 N1 C2 C9 176.95(14) . . . . ? C7 N1 C2 C3 -179.76(14) . . . . ? C6 N1 C2 C3 53.53(18) . . . . ? N1 C2 C3 C21 179.62(13) . . . . ? C8 C2 C3 C21 -59.52(17) . . . . ? C9 C2 C3 C21 56.42(17) . . . . ? N1 C2 C3 C4 -52.06(18) . . . . ? C8 C2 C3 C4 68.80(18) . . . . ? C9 C2 C3 C4 -175.26(14) . . . . ? C21 C3 C4 C5 -176.48(16) . . . . ? C2 C3 C4 C5 54.6(2) . . . . ? C3 C4 C5 C6 -57.5(2) . . . . ? C7 N1 C6 C5 174.08(17) . . . . ? C2 N1 C6 C5 -56.9(2) . . . . ? C4 C5 C6 N1 57.9(2) . . . . ? N1 C2 C8 N2 -23(3) . . . . ? C9 C2 C8 N2 96(3) . . . . ? C3 C2 C8 N2 -145(3) . . . . ? N1 C2 C9 C10 -52.30(17) . . . . ? C8 C2 C9 C10 -171.37(13) . . . . ? C3 C2 C9 C10 71.10(16) . . . . ? C2 C9 C10 S1 -170.44(11) . . . . ? O1 S1 C10 C9 60.41(14) . . . . ? O2 S1 C10 C9 -69.44(14) . . . . ? C11 S1 C10 C9 175.38(12) . . . . ? O1 S1 C11 C16 14.08(17) . . . . ? O2 S1 C11 C16 143.85(15) . . . . ? C10 S1 C11 C16 -101.19(15) . . . . ? O1 S1 C11 C12 -168.45(15) . . . . ? O2 S1 C11 C12 -38.68(17) . . . . ? C10 S1 C11 C12 76.28(16) . . . . ? C16 C11 C12 C13 -1.1(3) . . . . ? S1 C11 C12 C13 -178.54(17) . . . . ? C11 C12 C13 C14 -0.3(4) . . . . ? C12 C13 C14 C15 1.5(4) . . . . ? C13 C14 C15 C16 -1.2(4) . . . . ? C12 C11 C16 C15 1.4(3) . . . . ? S1 C11 C16 C15 178.82(16) . . . . ? C14 C15 C16 C11 -0.2(3) . . . . ? C4 C3 C21 C22 138.23(17) . . . . ? C2 C3 C21 C22 -94.50(18) . . . . ? C4 C3 C21 C26 -39.0(2) . . . . ? C2 C3 C21 C26 88.25(19) . . . . ? C26 C21 C22 C23 0.2(3) . . . . ? C3 C21 C22 C23 -177.24(17) . . . . ? C21 C22 C23 C24 1.1(3) . . . . ? C27 O3 C24 C23 -165.1(2) . . . . ? C27 O3 C24 C25 13.6(3) . . . . ? C22 C23 C24 O3 177.27(19) . . . . ? C22 C23 C24 C25 -1.5(3) . . . . ? O3 C24 C25 C26 -178.03(19) . . . . ? C23 C24 C25 C26 0.6(3) . . . . ? C24 C25 C26 C21 0.7(3) . . . . ? C22 C21 C26 C25 -1.1(3) . . . . ? C3 C21 C26 C25 176.27(17) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 71.22 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.623 _refine_diff_density_min -0.270 _refine_diff_density_rms 0.049