# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Juan Carlos Carretero' _publ_contact_author_address ; Quimica Organica Universidad Autonoma de Madrid carretera de comenar km 15 Madrid 28049 SPAIN ; _publ_contact_author_email JUANCARLOS.CARRETERO@UAM.ES _publ_section_title ; Enantioselective construction of stereogenic quaternary centres via Rh-catalyzed?asymmetric addition of alkenyl boronic acids to a,b-unsaturated pyridylsulfones ; loop_ _publ_author_name 'Juan Carlos Carretero' 'Pablo Mauleon' data_a1_m _database_code_depnum_ccdc_archive 'CCDC 274114' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H23 N O2 S' _chemical_formula_weight 377.48 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 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 7.9003(2) _cell_length_b 14.1271(3) _cell_length_c 17.2611(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1926.48(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.301 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 1.627 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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_type 'CCD area detector' _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 10238 _diffrn_reflns_av_R_equivalents 0.0291 _diffrn_reflns_av_sigmaI/netI 0.0281 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 4.04 _diffrn_reflns_theta_max 70.45 _reflns_number_total 3528 _reflns_number_gt 3411 _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 'Bruker SHELXTL' _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^)+(0.0448P)^2^+0.2498P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.010(13) _refine_ls_number_reflns 3528 _refine_ls_number_parameters 336 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0296 _refine_ls_R_factor_gt 0.0285 _refine_ls_wR_factor_ref 0.0737 _refine_ls_wR_factor_gt 0.0727 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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 0.14143(5) 0.19847(3) 0.38635(2) 0.02060(11) Uani 1 1 d . . . N1 N -0.18650(17) 0.17116(10) 0.37789(8) 0.0220(3) Uani 1 1 d . . . O1 O 0.15745(16) 0.11656(8) 0.43571(7) 0.0276(3) Uani 1 1 d . . . O2 O 0.27366(15) 0.21690(9) 0.33102(7) 0.0273(3) Uani 1 1 d . . . C1 C -0.0522(2) 0.18815(11) 0.33352(9) 0.0197(3) Uani 1 1 d . . . C2 C -0.0539(2) 0.19588(12) 0.25362(9) 0.0231(3) Uani 1 1 d . . . C3 C -0.2096(2) 0.18386(12) 0.21705(10) 0.0269(4) Uani 1 1 d . . . C4 C -0.3502(3) 0.16566(12) 0.26128(10) 0.0266(4) Uani 1 1 d . . . C5 C -0.3342(2) 0.15986(12) 0.34129(10) 0.0250(4) Uani 1 1 d . . . C6 C 0.1100(2) 0.29677(12) 0.45002(9) 0.0198(3) Uani 1 1 d . . . C7 C 0.1372(2) 0.39847(11) 0.41835(9) 0.0204(3) Uani 1 1 d . . . C8 C 0.0316(2) 0.41465(11) 0.34477(9) 0.0203(3) Uani 1 1 d . . . C9 C -0.1454(2) 0.40775(11) 0.34773(9) 0.0221(3) Uani 1 1 d . . . C10 C -0.2437(2) 0.42494(12) 0.28244(11) 0.0268(4) Uani 1 1 d . . . C11 C -0.1672(3) 0.45043(12) 0.21333(10) 0.0295(4) Uani 1 1 d . . . C12 C 0.0067(3) 0.45642(12) 0.20895(10) 0.0284(4) Uani 1 1 d . . . C13 C 0.1057(2) 0.43865(12) 0.27405(10) 0.0235(4) Uani 1 1 d . . . C14 C 0.3273(2) 0.41524(13) 0.40615(10) 0.0245(4) Uani 1 1 d . . . C15 C 0.0680(2) 0.46372(12) 0.48144(9) 0.0212(3) Uani 1 1 d . . . C16 C 0.1527(2) 0.52805(12) 0.52124(9) 0.0233(3) Uani 1 1 d . . . C17 C 0.0728(2) 0.58910(13) 0.58241(9) 0.0253(4) Uani 1 1 d . . . C18 C 0.0985(2) 0.69400(12) 0.56833(9) 0.0225(3) Uani 1 1 d . . . C19 C 0.0564(2) 0.73332(14) 0.49689(10) 0.0285(4) Uani 1 1 d . . . C20 C 0.0778(2) 0.82918(15) 0.48334(12) 0.0339(4) Uani 1 1 d . . . C21 C 0.1414(2) 0.88782(13) 0.54070(11) 0.0314(4) Uani 1 1 d . . . C22 C 0.1840(2) 0.84960(13) 0.61185(12) 0.0296(4) Uani 1 1 d . . . C23 C 0.1622(2) 0.75297(12) 0.62545(9) 0.0243(3) Uani 1 1 d . . . H2 H 0.043(2) 0.2078(12) 0.2272(10) 0.012(4) Uiso 1 1 d . . . H3 H -0.216(3) 0.1907(16) 0.1615(13) 0.037(6) Uiso 1 1 d . . . H4 H -0.458(3) 0.1581(15) 0.2385(13) 0.036(6) Uiso 1 1 d . . . H5 H -0.432(3) 0.1461(15) 0.3737(12) 0.031(5) Uiso 1 1 d . . . H6A H -0.003(2) 0.2885(12) 0.4704(10) 0.015(4) Uiso 1 1 d . . . H6B H 0.186(3) 0.2851(13) 0.4944(12) 0.027(5) Uiso 1 1 d . . . H9 H -0.199(2) 0.3909(13) 0.3979(11) 0.021(5) Uiso 1 1 d . . . H10 H -0.366(3) 0.4186(14) 0.2860(11) 0.025(5) Uiso 1 1 d . . . H11 H -0.239(3) 0.4635(17) 0.1689(15) 0.046(7) Uiso 1 1 d . . . H12 H 0.061(3) 0.4731(16) 0.1629(13) 0.038(6) Uiso 1 1 d . . . H13 H 0.224(3) 0.4424(14) 0.2723(12) 0.025(5) Uiso 1 1 d . . . H14A H 0.382(3) 0.4047(16) 0.4535(13) 0.038(6) Uiso 1 1 d . . . H14B H 0.349(2) 0.4794(13) 0.3902(10) 0.016(4) Uiso 1 1 d . . . H14C H 0.371(3) 0.3711(14) 0.3678(11) 0.025(5) Uiso 1 1 d . . . H15 H -0.051(3) 0.4560(14) 0.4927(11) 0.026(5) Uiso 1 1 d . . . H16 H 0.273(3) 0.5396(13) 0.5111(12) 0.025(5) Uiso 1 1 d . . . H17A H -0.049(3) 0.5759(14) 0.5829(11) 0.028(5) Uiso 1 1 d . . . H17B H 0.126(3) 0.5710(14) 0.6345(11) 0.024(5) Uiso 1 1 d . . . H19 H 0.012(3) 0.6906(15) 0.4579(12) 0.032(5) Uiso 1 1 d . . . H20 H 0.056(3) 0.8557(17) 0.4381(14) 0.041(6) Uiso 1 1 d . . . H21 H 0.159(3) 0.9564(16) 0.5342(12) 0.034(5) Uiso 1 1 d . . . H22 H 0.228(3) 0.8874(15) 0.6521(12) 0.030(5) Uiso 1 1 d . . . H23 H 0.185(2) 0.7257(13) 0.6756(11) 0.020(5) 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 S1 0.01909(19) 0.02047(19) 0.02224(18) -0.00209(15) -0.00103(16) 0.00213(14) N1 0.0207(7) 0.0239(7) 0.0214(6) -0.0006(6) 0.0009(6) 0.0004(5) O1 0.0284(7) 0.0234(6) 0.0311(6) -0.0008(5) -0.0066(6) 0.0045(5) O2 0.0211(6) 0.0303(7) 0.0304(6) -0.0070(5) 0.0023(5) 0.0014(5) C1 0.0226(8) 0.0148(7) 0.0218(7) -0.0032(7) -0.0004(6) 0.0009(6) C2 0.0253(9) 0.0221(8) 0.0220(8) -0.0003(7) 0.0034(7) -0.0017(7) C3 0.0352(10) 0.0249(9) 0.0205(8) -0.0005(7) -0.0034(7) 0.0007(7) C4 0.0244(9) 0.0274(9) 0.0281(8) -0.0026(7) -0.0063(8) 0.0010(7) C5 0.0208(8) 0.0277(8) 0.0265(8) 0.0012(7) 0.0004(8) -0.0001(7) C6 0.0202(8) 0.0205(8) 0.0187(7) -0.0006(6) -0.0017(6) 0.0002(6) C7 0.0192(8) 0.0213(8) 0.0207(7) -0.0018(6) -0.0007(7) -0.0011(6) C8 0.0254(8) 0.0145(7) 0.0210(8) -0.0042(6) -0.0002(7) -0.0005(6) C9 0.0229(8) 0.0196(7) 0.0238(8) -0.0039(6) -0.0020(7) 0.0020(7) C10 0.0275(10) 0.0224(8) 0.0306(9) -0.0031(7) -0.0074(8) 0.0021(7) C11 0.0419(11) 0.0218(8) 0.0247(8) -0.0005(7) -0.0123(9) 0.0002(8) C12 0.0437(11) 0.0216(8) 0.0198(8) -0.0001(7) 0.0002(8) -0.0069(8) C13 0.0275(10) 0.0186(8) 0.0244(8) -0.0013(7) -0.0002(7) -0.0034(6) C14 0.0225(9) 0.0269(9) 0.0241(8) -0.0011(7) 0.0004(7) -0.0035(7) C15 0.0207(8) 0.0221(8) 0.0209(7) 0.0017(6) 0.0007(7) -0.0012(6) C16 0.0240(9) 0.0243(8) 0.0218(7) -0.0007(6) -0.0003(7) -0.0006(7) C17 0.0300(10) 0.0260(9) 0.0200(7) -0.0033(7) 0.0007(7) -0.0042(7) C18 0.0195(8) 0.0256(9) 0.0223(7) -0.0017(7) 0.0026(6) -0.0001(6) C19 0.0265(9) 0.0351(10) 0.0240(8) -0.0010(8) -0.0029(8) -0.0008(7) C20 0.0278(9) 0.0406(11) 0.0332(9) 0.0106(8) 0.0001(8) 0.0043(8) C21 0.0243(9) 0.0236(8) 0.0465(10) 0.0030(8) 0.0102(9) 0.0038(7) C22 0.0277(9) 0.0265(9) 0.0347(9) -0.0069(8) 0.0042(9) -0.0014(7) C23 0.0250(8) 0.0260(8) 0.0218(7) -0.0043(7) 0.0019(7) -0.0005(7) _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 O2 1.4392(13) . ? S1 O1 1.4426(12) . ? S1 C1 1.7872(17) . ? S1 C6 1.7883(16) . ? N1 C1 1.330(2) . ? N1 C5 1.337(2) . ? C1 C2 1.383(2) . ? C2 C3 1.393(2) . ? C2 H2 0.905(18) . ? C3 C4 1.372(3) . ? C3 H3 0.96(2) . ? C4 C5 1.389(2) . ? C4 H4 0.95(2) . ? C5 H5 0.97(2) . ? C6 C7 1.552(2) . ? C6 H6A 0.967(19) . ? C6 H6B 0.99(2) . ? C7 C15 1.528(2) . ? C7 C14 1.535(2) . ? C7 C8 1.537(2) . ? C8 C13 1.395(2) . ? C8 C9 1.403(2) . ? C9 C10 1.390(2) . ? C9 H9 0.99(2) . ? C10 C11 1.385(3) . ? C10 H10 0.97(2) . ? C11 C12 1.378(3) . ? C11 H11 0.97(3) . ? C12 C13 1.392(3) . ? C12 H12 0.93(2) . ? C13 H13 0.93(2) . ? C14 H14A 0.94(2) . ? C14 H14B 0.963(19) . ? C14 H14C 0.97(2) . ? C15 C16 1.321(2) . ? C15 H15 0.97(2) . ? C16 C17 1.503(2) . ? C16 H16 0.98(2) . ? C17 C18 1.515(2) . ? C17 H17A 0.98(2) . ? C17 H17B 1.024(19) . ? C18 C23 1.386(2) . ? C18 C19 1.393(2) . ? C19 C20 1.385(3) . ? C19 H19 0.97(2) . ? C20 C21 1.385(3) . ? C20 H20 0.88(2) . ? C21 C22 1.383(3) . ? C21 H21 0.99(2) . ? C22 C23 1.396(2) . ? C22 H22 0.94(2) . ? C23 H23 0.964(19) . ? 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 O2 S1 O1 118.26(8) . . ? O2 S1 C1 107.32(7) . . ? O1 S1 C1 108.12(7) . . ? O2 S1 C6 111.60(7) . . ? O1 S1 C6 105.79(7) . . ? C1 S1 C6 104.95(7) . . ? C1 N1 C5 116.47(14) . . ? N1 C1 C2 125.50(16) . . ? N1 C1 S1 113.80(11) . . ? C2 C1 S1 120.68(13) . . ? C1 C2 C3 116.76(16) . . ? C1 C2 H2 120.6(11) . . ? C3 C2 H2 122.6(11) . . ? C4 C3 C2 119.04(16) . . ? C4 C3 H3 121.9(14) . . ? C2 C3 H3 119.0(14) . . ? C3 C4 C5 119.42(18) . . ? C3 C4 H4 121.3(14) . . ? C5 C4 H4 119.3(14) . . ? N1 C5 C4 122.81(17) . . ? N1 C5 H5 116.4(12) . . ? C4 C5 H5 120.8(12) . . ? C7 C6 S1 118.89(11) . . ? C7 C6 H6A 111.6(10) . . ? S1 C6 H6A 105.0(10) . . ? C7 C6 H6B 110.1(11) . . ? S1 C6 H6B 105.3(11) . . ? H6A C6 H6B 104.9(15) . . ? C15 C7 C14 110.78(14) . . ? C15 C7 C8 107.76(13) . . ? C14 C7 C8 113.26(13) . . ? C15 C7 C6 104.94(12) . . ? C14 C7 C6 109.08(14) . . ? C8 C7 C6 110.70(13) . . ? C13 C8 C9 117.83(16) . . ? C13 C8 C7 122.10(15) . . ? C9 C8 C7 120.05(15) . . ? C10 C9 C8 121.01(17) . . ? C10 C9 H9 120.8(11) . . ? C8 C9 H9 118.2(11) . . ? C11 C10 C9 120.02(18) . . ? C11 C10 H10 120.8(12) . . ? C9 C10 H10 119.2(12) . . ? C12 C11 C10 119.86(17) . . ? C12 C11 H11 121.7(15) . . ? C10 C11 H11 118.4(15) . . ? C11 C12 C13 120.32(18) . . ? C11 C12 H12 121.3(15) . . ? C13 C12 H12 118.4(15) . . ? C12 C13 C8 120.94(17) . . ? C12 C13 H13 121.7(13) . . ? C8 C13 H13 117.4(13) . . ? C7 C14 H14A 107.9(14) . . ? C7 C14 H14B 111.1(11) . . ? H14A C14 H14B 108.4(18) . . ? C7 C14 H14C 110.0(13) . . ? H14A C14 H14C 109.1(17) . . ? H14B C14 H14C 110.2(15) . . ? C16 C15 C7 127.17(17) . . ? C16 C15 H15 117.8(12) . . ? C7 C15 H15 115.0(12) . . ? C15 C16 C17 123.18(17) . . ? C15 C16 H16 120.9(12) . . ? C17 C16 H16 115.9(12) . . ? C16 C17 C18 113.10(14) . . ? C16 C17 H17A 108.0(12) . . ? C18 C17 H17A 108.7(12) . . ? C16 C17 H17B 107.6(11) . . ? C18 C17 H17B 109.3(11) . . ? H17A C17 H17B 110.2(16) . . ? C23 C18 C19 118.50(16) . . ? C23 C18 C17 121.49(14) . . ? C19 C18 C17 120.01(15) . . ? C20 C19 C18 120.70(18) . . ? C20 C19 H19 122.3(12) . . ? C18 C19 H19 117.0(12) . . ? C19 C20 C21 120.55(18) . . ? C19 C20 H20 122.8(16) . . ? C21 C20 H20 116.6(16) . . ? C22 C21 C20 119.30(17) . . ? C22 C21 H21 116.8(12) . . ? C20 C21 H21 123.9(12) . . ? C21 C22 C23 120.08(18) . . ? C21 C22 H22 121.5(13) . . ? C23 C22 H22 118.4(13) . . ? C18 C23 C22 120.87(17) . . ? C18 C23 H23 117.7(11) . . ? C22 C23 H23 121.3(11) . . ? 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 N1 C1 C2 0.7(2) . . . . ? C5 N1 C1 S1 -178.02(12) . . . . ? O2 S1 C1 N1 -179.83(11) . . . . ? O1 S1 C1 N1 51.58(13) . . . . ? C6 S1 C1 N1 -60.98(13) . . . . ? O2 S1 C1 C2 1.38(16) . . . . ? O1 S1 C1 C2 -127.21(14) . . . . ? C6 S1 C1 C2 120.23(14) . . . . ? N1 C1 C2 C3 -0.7(3) . . . . ? S1 C1 C2 C3 177.99(12) . . . . ? C1 C2 C3 C4 0.2(3) . . . . ? C2 C3 C4 C5 0.1(3) . . . . ? C1 N1 C5 C4 -0.3(2) . . . . ? C3 C4 C5 N1 -0.1(3) . . . . ? O2 S1 C6 C7 33.39(15) . . . . ? O1 S1 C6 C7 163.27(12) . . . . ? C1 S1 C6 C7 -82.52(14) . . . . ? S1 C6 C7 C15 169.44(11) . . . . ? S1 C6 C7 C14 -71.81(16) . . . . ? S1 C6 C7 C8 53.45(18) . . . . ? C15 C7 C8 C13 125.18(16) . . . . ? C14 C7 C8 C13 2.3(2) . . . . ? C6 C7 C8 C13 -120.59(16) . . . . ? C15 C7 C8 C9 -53.22(19) . . . . ? C14 C7 C8 C9 -176.12(15) . . . . ? C6 C7 C8 C9 61.02(19) . . . . ? C13 C8 C9 C10 -0.4(2) . . . . ? C7 C8 C9 C10 178.02(15) . . . . ? C8 C9 C10 C11 -0.8(3) . . . . ? C9 C10 C11 C12 1.6(3) . . . . ? C10 C11 C12 C13 -1.2(3) . . . . ? C11 C12 C13 C8 -0.1(3) . . . . ? C9 C8 C13 C12 0.9(2) . . . . ? C7 C8 C13 C12 -177.55(15) . . . . ? C14 C7 C15 C16 1.0(2) . . . . ? C8 C7 C15 C16 -123.44(18) . . . . ? C6 C7 C15 C16 118.55(18) . . . . ? C7 C15 C16 C17 179.96(15) . . . . ? C15 C16 C17 C18 -125.06(18) . . . . ? C16 C17 C18 C23 -128.44(18) . . . . ? C16 C17 C18 C19 52.1(2) . . . . ? C23 C18 C19 C20 0.0(3) . . . . ? C17 C18 C19 C20 179.46(17) . . . . ? C18 C19 C20 C21 0.0(3) . . . . ? C19 C20 C21 C22 0.1(3) . . . . ? C20 C21 C22 C23 -0.2(3) . . . . ? C19 C18 C23 C22 -0.1(3) . . . . ? C17 C18 C23 C22 -179.52(16) . . . . ? C21 C22 C23 C18 0.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 70.45 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.222 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.039