Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2001 data_c _database_code_CSD 160079 _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'F.S.Mair' 'R.Manning' 'R.J.Pritchard' 'J.E.Warren' _publ_contact_author_name 'F.S.Mair' _publ_contact_author_address ; ? ; _publ_contact_author_email 'frank.mair@umist.ac.uk' _audit_creation_date 2000-04-04T10:18:09-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.1beta5 _audit_conform_dict_location ; ftp://ftp.iucr.org/cifdics/cif_core_2.1beta5.dic ; _publ_requested_category FO #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C26 H36 B1 N2 Cl3' _chemical_formula_structural 'C26 H36 B1 N2 CL3' _chemical_formula_sum 'C26 H36 B Cl3 N2' _chemical_formula_weight 493.73 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.323(4) _cell_length_b 9.8086(3) _cell_length_c 17.35350(10) _cell_angle_alpha 93.246(3) _cell_angle_beta 90.208(2) _cell_angle_gamma 115.0350(10) _cell_volume 1281.0(6) _cell_formula_units_Z 2 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour clear _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_diffrn 1.28 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 524 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.375 _exptl_absorpt_factor_muR 0.047 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 7 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied. ; _exptl_absorpt_correction_T_min 0.8812 _exptl_absorpt_correction_T_max 0.9531 _exptl_absorpt_correction_T_ave 0.9236 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'scintillation LiI' _diffrn_detector_dtime 1.195 _diffrn_orient_matrix_type ; x-axis points to radiation source the matrix is specified in reciprocal space ; _diffrn_orient_matrix_ub_11 0.38482E-1 _diffrn_orient_matrix_ub_12 0.1108 _diffrn_orient_matrix_ub_13 -0.3406E-2 _diffrn_orient_matrix_ub_21 -0.125594 _diffrn_orient_matrix_ub_22 -0.18105E-1 _diffrn_orient_matrix_ub_23 -0.11268E-1 _diffrn_orient_matrix_ub_31 -0.18582E-1 _diffrn_orient_matrix_ub_32 0.01046 _diffrn_orient_matrix_ub_33 0.56532E-1 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 2 _diffrn_standards_decay_corr_max 1.056 _diffrn_standards_decay_corr_min 0.903 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -1 -5 6 -5 1 5 -5 3 -8 _diffrn_reflns_number 4812 _diffrn_reflns_av_R_equivalents 0.0199 _diffrn_reflns_av_sigmaI/netI 0.0278 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.3 _diffrn_reflns_theta_max 24.97 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 4475 _reflns_number_gt 3324 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0789P)^2^+0.3057P] 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_number_reflns 4475 _refine_ls_number_parameters 433 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.067 _refine_ls_R_factor_gt 0.0445 _refine_ls_wR_factor_ref 0.1257 _refine_ls_wR_factor_gt 0.1134 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.416 _refine_diff_density_min -0.413 _refine_diff_density_rms 0.058 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group B1 B 0.7157(4) 0.0001(3) 0.25024(16) 0.0235(6) Uani 1 d . . . N1 N 0.7979(3) -0.0316(2) 0.31313(11) 0.0228(4) Uani 1 d . . . N4 N 0.8292(3) 0.0315(2) 0.18665(11) 0.0228(4) Uani 1 d . . . Cl3 Cl 1.17157(9) 0.22560(8) 0.22408(4) 0.0398(2) Uani 1 d . . . Cl2 Cl 0.94597(10) -0.22566(8) 0.27598(4) 0.0401(2) Uani 1 d . . . Cl1 Cl 0.50629(9) 0.00001(8) 0.25001(4) 0.03277(19) Uani 1 d . . . C2 C 0.9592(3) -0.0337(3) 0.28947(14) 0.0250(5) Uani 1 d . . . C3 C 0.9931(3) 0.0335(3) 0.21061(14) 0.0255(5) Uani 1 d . . . C5 C 0.7977(3) 0.0604(3) 0.10930(13) 0.0239(5) Uani 1 d . . . C6 C 0.7557(3) -0.0564(3) 0.05187(14) 0.0270(5) Uani 1 d . . . C7 C 0.7255(4) -0.0265(3) -0.02296(16) 0.0353(6) Uani 1 d . . . C8 C 0.7352(4) 0.1119(3) -0.03938(16) 0.0376(7) Uani 1 d . . . C9 C 0.7729(4) 0.2233(3) 0.01782(15) 0.0339(6) Uani 1 d . . . C10 C 0.8056(3) 0.2010(3) 0.09391(14) 0.0270(5) Uani 1 d . . . C11 C 0.8449(4) 0.3285(3) 0.15469(16) 0.0321(6) Uani 1 d . . . C12 C 1.0090(5) 0.4690(4) 0.1361(2) 0.0447(8) Uani 1 d . . . C13 C 0.6873(5) 0.3665(4) 0.1647(2) 0.0456(8) Uani 1 d . . . C14 C 0.7323(4) -0.2126(3) 0.07118(16) 0.0319(6) Uani 1 d . . . C15 C 0.7597(5) -0.3027(4) 0.00271(19) 0.0450(7) Uani 1 d . . . C16 C 0.5512(4) -0.3018(3) 0.10583(19) 0.0391(7) Uani 1 d . . . C17 C 0.7371(3) -0.0609(3) 0.39092(13) 0.0238(5) Uani 1 d . . . C18 C 0.6047(3) -0.2012(3) 0.40612(14) 0.0277(5) Uani 1 d . . . C19 C 0.5491(4) -0.2236(3) 0.48186(15) 0.0338(6) Uani 1 d . . . C20 C 0.6236(4) -0.1122(3) 0.53941(16) 0.0382(7) Uani 1 d . . . C21 C 0.7520(4) 0.0263(3) 0.52306(16) 0.0347(6) Uani 1 d . . . C22 C 0.8125(3) 0.0563(3) 0.44840(14) 0.0281(6) Uani 1 d . . . C23 C 0.9450(4) 0.2123(3) 0.42881(16) 0.0335(6) Uani 1 d . . . C24 C 0.8529(4) 0.3020(4) 0.3942(2) 0.0405(7) Uani 1 d . . . C25 C 1.0620(5) 0.3025(4) 0.4975(2) 0.0453(7) Uani 1 d . . . C26 C 0.5403(5) -0.4688(4) 0.3641(2) 0.0440(8) Uani 1 d . . . C27 C 0.5161(4) -0.3281(3) 0.34542(16) 0.0333(6) Uani 1 d . . . C28 C 0.3201(4) -0.3666(4) 0.3351(2) 0.0462(8) Uani 1 d . . . H2 H 1.066(4) 0.006(3) 0.3283(17) 0.036(8) Uiso 1 d . . . H3 H 1.058(4) -0.007(3) 0.1707(17) 0.040(8) Uiso 1 d . . . H7 H 0.696(3) -0.097(3) -0.0620(17) 0.027(7) Uiso 1 d . . . H9 H 0.776(4) 0.324(3) 0.0076(16) 0.033(7) Uiso 1 d . . . H8 H 0.704(4) 0.121(3) -0.088(2) 0.045(9) Uiso 1 d . . . H11 H 0.876(3) 0.300(3) 0.2011(16) 0.025(7) Uiso 1 d . . . H12A H 1.103(5) 0.448(4) 0.125(2) 0.055(11) Uiso 1 d . . . H12B H 1.039(4) 0.555(4) 0.176(2) 0.056(10) Uiso 1 d . . . H12C H 0.988(5) 0.508(4) 0.091(2) 0.062(11) Uiso 1 d . . . H13A H 0.591(5) 0.282(4) 0.181(2) 0.056(10) Uiso 1 d . . . H13B H 0.725(4) 0.445(4) 0.205(2) 0.049(9) Uiso 1 d . . . H13C H 0.658(6) 0.398(5) 0.117(3) 0.086(14) Uiso 1 d . . . H14 H 0.826(4) -0.195(3) 0.1056(16) 0.025(7) Uiso 1 d . . . H15A H 0.659(5) -0.332(4) -0.036(2) 0.062(11) Uiso 1 d . . . H15B H 0.876(5) -0.234(4) -0.022(2) 0.061(10) Uiso 1 d . . . H15C H 0.757(5) -0.402(5) 0.023(2) 0.077(12) Uiso 1 d . . . H16A H 0.454(5) -0.330(4) 0.071(2) 0.050(10) Uiso 1 d . . . H16B H 0.539(5) -0.396(4) 0.124(2) 0.057(10) Uiso 1 d . . . H16C H 0.511(6) -0.257(5) 0.148(3) 0.083(13) Uiso 1 d . . . H19 H 0.455(3) -0.324(3) 0.4919(15) 0.022(6) Uiso 1 d . . . H20 H 0.580(4) -0.126(3) 0.587(2) 0.044(9) Uiso 1 d . . . H21 H 0.798(4) 0.101(3) 0.5619(17) 0.031(7) Uiso 1 d . . . H23 H 1.019(3) 0.196(3) 0.3922(15) 0.017(6) Uiso 1 d . . . H24B H 0.788(5) 0.328(4) 0.430(2) 0.062(11) Uiso 1 d . . . H24A H 0.770(5) 0.250(4) 0.354(2) 0.066(11) Uiso 1 d . . . H24C H 0.938(4) 0.402(4) 0.3808(19) 0.050(9) Uiso 1 d . . . H25A H 1.158(5) 0.396(4) 0.481(2) 0.064(11) Uiso 1 d . . . H25C H 0.991(5) 0.336(4) 0.533(2) 0.065(11) Uiso 1 d . . . H25B H 1.114(4) 0.233(4) 0.527(2) 0.051(9) Uiso 1 d . . . H26A H 0.661(5) -0.443(4) 0.3745(19) 0.045(9) Uiso 1 d . . . H26B H 0.505(4) -0.538(4) 0.325(2) 0.047(9) Uiso 1 d . . . H26C H 0.476(6) -0.511(5) 0.406(3) 0.081(13) Uiso 1 d . . . H27 H 0.577(4) -0.293(3) 0.3018(18) 0.034(8) Uiso 1 d . . . H28A H 0.308(5) -0.277(5) 0.320(2) 0.066(11) Uiso 1 d . . . H28B H 0.279(4) -0.442(4) 0.297(2) 0.050(10) Uiso 1 d . . . H28C H 0.254(5) -0.401(4) 0.385(2) 0.073(12) Uiso 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 B1 0.0334(15) 0.0203(13) 0.0183(13) 0.0018(10) 0.0028(11) 0.0127(11) N1 0.0288(11) 0.0276(11) 0.0135(10) 0.0029(8) 0.0021(8) 0.0131(9) N4 0.0296(11) 0.0260(11) 0.0145(10) 0.0049(8) 0.0027(8) 0.0129(9) Cl3 0.0362(4) 0.0361(4) 0.0384(4) 0.0070(3) 0.0018(3) 0.0063(3) Cl2 0.0555(5) 0.0368(4) 0.0390(4) 0.0073(3) 0.0065(3) 0.0295(3) Cl1 0.0335(4) 0.0444(4) 0.0261(3) 0.0071(3) 0.0040(2) 0.0214(3) C2 0.0310(13) 0.0277(13) 0.0192(12) 0.0025(10) -0.0002(10) 0.0152(11) C3 0.0290(13) 0.0265(13) 0.0198(13) 0.0022(10) 0.0027(10) 0.0105(11) C5 0.0291(13) 0.0294(13) 0.0144(11) 0.0055(10) 0.0029(9) 0.0128(10) C6 0.0324(14) 0.0310(14) 0.0203(12) 0.0048(10) 0.0008(10) 0.0157(11) C7 0.0482(17) 0.0396(16) 0.0201(13) -0.0028(12) -0.0027(11) 0.0212(14) C8 0.0498(17) 0.0476(18) 0.0181(14) 0.0084(12) -0.0025(12) 0.0224(14) C9 0.0437(16) 0.0382(16) 0.0254(14) 0.0114(12) 0.0022(11) 0.0217(13) C10 0.0311(13) 0.0299(13) 0.0222(13) 0.0083(10) 0.0053(10) 0.0141(11) C11 0.0474(17) 0.0277(14) 0.0255(14) 0.0064(11) 0.0036(12) 0.0195(12) C12 0.059(2) 0.0305(16) 0.0429(19) 0.0025(14) 0.0037(15) 0.0168(15) C13 0.062(2) 0.0407(19) 0.0438(19) 0.0052(16) 0.0107(16) 0.0308(17) C14 0.0419(16) 0.0312(14) 0.0257(14) -0.0027(11) -0.0068(12) 0.0190(12) C15 0.059(2) 0.0409(18) 0.0391(18) -0.0044(14) 0.0025(16) 0.0264(16) C16 0.0491(19) 0.0312(16) 0.0396(17) 0.0068(13) 0.0053(14) 0.0189(14) C17 0.0298(13) 0.0301(13) 0.0145(11) 0.0057(10) 0.0027(9) 0.0150(11) C18 0.0328(14) 0.0318(14) 0.0212(13) 0.0065(10) 0.0010(10) 0.0159(11) C19 0.0396(16) 0.0342(15) 0.0278(14) 0.0121(12) 0.0103(11) 0.0145(13) C20 0.0481(17) 0.0471(18) 0.0199(14) 0.0090(12) 0.0105(12) 0.0196(14) C21 0.0429(16) 0.0387(16) 0.0205(13) -0.0020(12) 0.0012(11) 0.0159(13) C22 0.0322(14) 0.0338(14) 0.0196(12) 0.0026(10) 0.0029(10) 0.0152(11) C23 0.0387(16) 0.0312(15) 0.0275(14) -0.0003(11) 0.0076(12) 0.0119(12) C24 0.0434(18) 0.0348(17) 0.0381(18) 0.0041(14) -0.0010(14) 0.0112(14) C25 0.0437(18) 0.0416(18) 0.0421(18) -0.0020(15) -0.0042(14) 0.0105(15) C26 0.053(2) 0.0316(16) 0.0428(19) 0.0036(15) 0.0023(16) 0.0136(15) C27 0.0380(15) 0.0279(14) 0.0288(15) 0.0066(12) 0.0030(12) 0.0083(12) C28 0.0414(18) 0.0418(19) 0.045(2) 0.0061(16) -0.0029(14) 0.0073(15) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 B1 N1 1.403(3) . ? B1 N4 1.416(3) . ? B1 Cl1 1.743(3) . ? N1 C2 1.413(3) . ? N1 C17 1.445(3) . ? N4 C3 1.417(3) . ? N4 C5 1.433(3) . ? Cl3 C3 1.841(3) . ? Cl2 C2 1.840(3) . ? C2 C3 1.528(3) . ? C5 C10 1.394(3) . ? C5 C6 1.399(4) . ? C6 C7 1.392(4) . ? C6 C14 1.517(4) . ? C7 C8 1.372(4) . ? C8 C9 1.365(4) . ? C9 C10 1.395(4) . ? C10 C11 1.512(4) . ? C11 C13 1.516(4) . ? C11 C12 1.526(4) . ? C14 C15 1.516(4) . ? C14 C16 1.532(4) . ? C17 C18 1.392(4) . ? C17 C22 1.402(4) . ? C18 C19 1.393(4) . ? C18 C27 1.507(4) . ? C19 C20 1.369(4) . ? C20 C21 1.374(4) . ? C21 C22 1.393(4) . ? C22 C23 1.519(4) . ? C23 C25 1.514(4) . ? C23 C24 1.532(4) . ? C26 C27 1.528(4) . ? C27 C28 1.519(4) . ? 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 N1 B1 N4 109.4(2) . . ? N1 B1 Cl1 125.5(2) . . ? N4 B1 Cl1 125.1(2) . . ? B1 N1 C2 109.10(19) . . ? B1 N1 C17 128.9(2) . . ? C2 N1 C17 121.98(19) . . ? B1 N4 C3 108.82(19) . . ? B1 N4 C5 129.4(2) . . ? C3 N4 C5 121.78(19) . . ? N1 C2 C3 105.45(19) . . ? N1 C2 Cl2 112.93(17) . . ? C3 C2 Cl2 107.26(16) . . ? N4 C3 C2 105.05(19) . . ? N4 C3 Cl3 112.85(17) . . ? C2 C3 Cl3 107.51(17) . . ? C10 C5 C6 122.2(2) . . ? C10 C5 N4 119.6(2) . . ? C6 C5 N4 118.2(2) . . ? C7 C6 C5 117.4(2) . . ? C7 C6 C14 121.1(2) . . ? C5 C6 C14 121.3(2) . . ? C8 C7 C6 121.1(3) . . ? C9 C8 C7 120.5(3) . . ? C8 C9 C10 121.3(3) . . ? C5 C10 C9 117.4(2) . . ? C5 C10 C11 123.9(2) . . ? C9 C10 C11 118.7(2) . . ? C10 C11 C13 111.4(3) . . ? C10 C11 C12 111.7(2) . . ? C13 C11 C12 110.1(3) . . ? C15 C14 C6 113.0(2) . . ? C15 C14 C16 110.1(3) . . ? C6 C14 C16 111.7(2) . . ? C18 C17 C22 122.4(2) . . ? C18 C17 N1 119.7(2) . . ? C22 C17 N1 117.9(2) . . ? C17 C18 C19 117.6(2) . . ? C17 C18 C27 123.9(2) . . ? C19 C18 C27 118.5(2) . . ? C20 C19 C18 121.2(3) . . ? C19 C20 C21 120.4(3) . . ? C20 C21 C22 121.3(3) . . ? C21 C22 C17 117.2(2) . . ? C21 C22 C23 121.5(2) . . ? C17 C22 C23 121.2(2) . . ? C25 C23 C22 112.7(2) . . ? C25 C23 C24 109.7(3) . . ? C22 C23 C24 111.7(2) . . ? C18 C27 C28 111.6(3) . . ? C18 C27 C26 111.5(2) . . ? C28 C27 C26 109.9(3) . . ?