# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name _publ_author_footnote _publ_author_address 'Rik Tykwinski' . ; Department of Chemistry University of Alberta Edmonton, Alberta T6G 2G2 Canada ; 'Manuel Chaur' . ; Department of Chemistry Clemson University Clemson, South Carolina 29634 U.S.A. ; 'Luis Echegoyen' . ; Department of Chemistry University of Alberta Edmonton, Alberta T6G 2G2 Canada ; 'Michael J. Ferguson' 'X-ray Crystallography Laboratory' ; Department of Chemistry University of Alberta Edmonton, Alberta T6G 2G2 Canada ; 'Mojtaba Gholami' 'X-ray Crystallography Laboratory' ; Department of Chemistry University of Alberta Edmonton, Alberta T6G 2G2 Canada ; ; R.McDonald ; . ; Department of Chemistry Clemson University Clemson, South Carolina 29634 U.S.A. ; 'Myron Wilde' . ; Department of Chemistry University of Alberta Edmonton, Alberta T6G 2G2 Canada ; _publ_contact_author_name 'Rik Tykwinski' _publ_contact_author_email RIK.TYKWINSKI@UALBERTA.CA _publ_section_title ; Radiaannulenes: Synthesis, electrochemistry, and solid-state structure ; _publ_contact_author_address ; Department of Chemistry University of Alberta Edmonton, Alberta T6G 2G2 Canada ; _publ_contact_author_fax 1(780)4928231 _publ_contact_author_phone 1(780)4925307 _publ_contact_letter ; To: Cambridge Crystallographic Data Centre Please accept the following CIF data for a structure we hope to publish in Chemical Communications. Please forward any questions concerning this CIF to Bob McDonald (Bob.McDonald@ualberta.ca). ; # Attachment 'Gholami.CC2009.cif' data_3a _database_code_depnum_ccdc_archive 'CCDC 721525' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C48 H28' _chemical_formula_sum 'C48 H28' _chemical_formula_weight 604.70 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.7217(9) _cell_length_b 30.219(4) _cell_length_c 8.2151(11) _cell_angle_alpha 90.00 _cell_angle_beta 101.073(2) _cell_angle_gamma 90.00 _cell_volume 1637.6(4) _cell_formula_units_Z 2 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 5323 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 27.41 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.226 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9667 _exptl_absorpt_correction_T_max 0.9951 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker PLATFORM diffractometer/SMART 1000 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 13960 _diffrn_reflns_av_R_equivalents 0.0314 _diffrn_reflns_av_sigmaI/netI 0.0274 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -39 _diffrn_reflns_limit_k_max 39 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 27.52 _reflns_number_total 3770 _reflns_number_gt 2870 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART (Bruker, 1997)' _computing_cell_refinement 'Bruker SAINT (Bruker, 1997)' _computing_data_reduction 'Bruker SAINT (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL (Bruker, 1997)' _computing_publication_material 'Bruker SHELXTL (Bruker, 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^)+(0.0613P)^2^+0.3326P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3770 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0660 _refine_ls_R_factor_gt 0.0464 _refine_ls_wR_factor_ref 0.1258 _refine_ls_wR_factor_gt 0.1158 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 C1 C -0.2967(2) -0.04434(4) 0.42856(17) 0.0311(3) Uani 1 1 d . . . C2 C -0.3621(2) -0.01418(4) 0.33987(17) 0.0316(3) Uani 1 1 d . . . C3 C -0.4545(2) 0.01941(4) 0.22699(16) 0.0301(3) Uani 1 1 d . . . C4 C -0.6566(2) 0.01511(5) 0.14800(17) 0.0358(3) Uani 1 1 d . . . H4 H -0.7329 -0.0098 0.1711 0.043 Uiso 1 1 calc R . . C5 C -0.7468(2) 0.04674(5) 0.03648(18) 0.0408(4) Uani 1 1 d . . . H5 H -0.8850 0.0436 -0.0156 0.049 Uiso 1 1 calc R . . C6 C -0.6373(2) 0.08287(5) 0.00018(19) 0.0418(4) Uani 1 1 d . . . H6 H -0.6997 0.1042 -0.0781 0.050 Uiso 1 1 calc R . . C7 C -0.4372(2) 0.08800(5) 0.07753(18) 0.0370(3) Uani 1 1 d . . . H7 H -0.3629 0.1130 0.0525 0.044 Uiso 1 1 calc R . . C8 C -0.3430(2) 0.05667(4) 0.19247(16) 0.0307(3) Uani 1 1 d . . . C9 C -0.1393(2) 0.06316(4) 0.27808(17) 0.0315(3) Uani 1 1 d . . . C10 C 0.0255(2) 0.07140(4) 0.35776(17) 0.0312(3) Uani 1 1 d . . . C11 C 0.2156(2) 0.08028(4) 0.46494(17) 0.0305(3) Uani 1 1 d . . . C12 C 0.3089(2) 0.12061(4) 0.47136(17) 0.0329(3) Uani 1 1 d . . . C13 C 0.2189(2) 0.15799(4) 0.36409(18) 0.0365(3) Uani 1 1 d . . . C14 C 0.0187(2) 0.17154(5) 0.3533(2) 0.0424(4) Uani 1 1 d . . . H14 H -0.0664 0.1564 0.4148 0.051 Uiso 1 1 calc R . . C15 C -0.0572(3) 0.20705(5) 0.2534(2) 0.0548(5) Uani 1 1 d . . . H15 H -0.1937 0.2161 0.2478 0.066 Uiso 1 1 calc R . . C16 C 0.0623(4) 0.22918(6) 0.1628(2) 0.0620(5) Uani 1 1 d . . . H16 H 0.0092 0.2536 0.0952 0.074 Uiso 1 1 calc R . . C17 C 0.2605(4) 0.21588(6) 0.1701(2) 0.0622(5) Uani 1 1 d . . . H17 H 0.3428 0.2307 0.1054 0.075 Uiso 1 1 calc R . . C18 C 0.3394(3) 0.18092(5) 0.2720(2) 0.0499(4) Uani 1 1 d . . . H18 H 0.4770 0.1725 0.2790 0.060 Uiso 1 1 calc R . . C19 C 0.5029(2) 0.12986(5) 0.58768(18) 0.0357(3) Uani 1 1 d . . . C20 C 0.5214(3) 0.16883(5) 0.6808(2) 0.0487(4) Uani 1 1 d . . . H20 H 0.4112 0.1890 0.6676 0.058 Uiso 1 1 calc R . . C21 C 0.6988(3) 0.17836(6) 0.7921(2) 0.0570(5) Uani 1 1 d . . . H21 H 0.7083 0.2047 0.8563 0.068 Uiso 1 1 calc R . . C22 C 0.8615(3) 0.14980(6) 0.8101(2) 0.0524(4) Uani 1 1 d . . . H22 H 0.9834 0.1566 0.8855 0.063 Uiso 1 1 calc R . . C23 C 0.8466(2) 0.11133(6) 0.7183(2) 0.0446(4) Uani 1 1 d . . . H23 H 0.9586 0.0916 0.7305 0.054 Uiso 1 1 calc R . . C24 C 0.6682(2) 0.10127(5) 0.60791(18) 0.0374(3) Uani 1 1 d . . . H24 H 0.6590 0.0746 0.5457 0.045 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 C1 0.0301(7) 0.0289(7) 0.0344(7) -0.0008(5) 0.0061(5) -0.0039(5) C2 0.0319(7) 0.0301(7) 0.0329(7) -0.0030(5) 0.0066(5) -0.0044(5) C3 0.0332(7) 0.0293(7) 0.0279(7) -0.0030(5) 0.0064(5) 0.0012(5) C4 0.0343(7) 0.0380(7) 0.0347(7) -0.0016(6) 0.0059(6) -0.0034(6) C5 0.0329(8) 0.0508(9) 0.0365(8) -0.0011(7) 0.0013(6) 0.0045(6) C6 0.0445(9) 0.0421(8) 0.0365(8) 0.0056(6) 0.0016(7) 0.0090(7) C7 0.0418(8) 0.0320(7) 0.0368(7) 0.0041(6) 0.0068(6) 0.0004(6) C8 0.0330(7) 0.0299(7) 0.0293(7) -0.0025(5) 0.0064(5) 0.0022(5) C9 0.0358(8) 0.0262(6) 0.0334(7) 0.0011(5) 0.0084(6) 0.0000(5) C10 0.0341(7) 0.0257(6) 0.0347(7) 0.0019(5) 0.0088(6) 0.0000(5) C11 0.0312(7) 0.0285(7) 0.0322(7) 0.0000(5) 0.0072(5) 0.0000(5) C12 0.0344(7) 0.0301(7) 0.0341(7) 0.0004(5) 0.0066(6) -0.0016(6) C13 0.0446(8) 0.0272(7) 0.0355(7) -0.0003(5) 0.0022(6) -0.0044(6) C14 0.0487(9) 0.0317(8) 0.0444(8) 0.0001(6) 0.0026(7) 0.0007(6) C15 0.0635(11) 0.0352(8) 0.0574(11) 0.0008(7) -0.0087(9) 0.0064(8) C16 0.0935(16) 0.0324(9) 0.0499(10) 0.0093(7) -0.0121(10) -0.0009(9) C17 0.0953(16) 0.0385(9) 0.0524(11) 0.0086(8) 0.0136(10) -0.0166(10) C18 0.0604(11) 0.0365(8) 0.0540(10) 0.0053(7) 0.0139(8) -0.0078(7) C19 0.0380(8) 0.0316(7) 0.0364(7) 0.0034(6) 0.0046(6) -0.0077(6) C20 0.0534(10) 0.0312(8) 0.0565(10) -0.0019(7) -0.0023(8) -0.0040(7) C21 0.0695(12) 0.0393(9) 0.0553(10) -0.0058(8) -0.0056(9) -0.0148(8) C22 0.0482(10) 0.0579(11) 0.0456(9) 0.0023(8) -0.0048(7) -0.0187(8) C23 0.0353(8) 0.0573(10) 0.0408(8) 0.0066(7) 0.0059(6) -0.0046(7) C24 0.0357(8) 0.0423(8) 0.0353(7) 0.0006(6) 0.0095(6) -0.0057(6) _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 C1 C2 1.1966(19) . ? C1 C11 1.4347(19) 3_556 ? C2 C3 1.4334(19) . ? C3 C4 1.3945(19) . ? C3 C8 1.4113(18) . ? C4 C5 1.381(2) . ? C5 C6 1.381(2) . ? C6 C7 1.381(2) . ? C7 C8 1.3996(19) . ? C8 C9 1.4278(19) . ? C9 C10 1.1994(19) . ? C10 C11 1.4312(19) . ? C11 C12 1.3673(18) . ? C11 C1 1.4347(19) 3_556 ? C12 C19 1.4873(19) . ? C12 C13 1.4879(19) . ? C13 C14 1.393(2) . ? C13 C18 1.395(2) . ? C14 C15 1.387(2) . ? C15 C16 1.370(3) . ? C16 C17 1.382(3) . ? C17 C18 1.388(2) . ? C19 C24 1.392(2) . ? C19 C20 1.397(2) . ? C20 C21 1.386(2) . ? C21 C22 1.379(3) . ? C22 C23 1.379(2) . ? C23 C24 1.391(2) . ? 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 C1 C11 179.22(15) . 3_556 ? C1 C2 C3 174.97(14) . . ? C4 C3 C8 119.22(12) . . ? C4 C3 C2 119.83(12) . . ? C8 C3 C2 120.94(12) . . ? C5 C4 C3 120.56(13) . . ? C4 C5 C6 120.43(14) . . ? C5 C6 C7 120.09(14) . . ? C6 C7 C8 120.59(13) . . ? C7 C8 C3 119.10(12) . . ? C7 C8 C9 120.42(12) . . ? C3 C8 C9 120.44(12) . . ? C10 C9 C8 174.33(14) . . ? C9 C10 C11 175.21(14) . . ? C12 C11 C10 122.66(12) . . ? C12 C11 C1 122.23(12) . 3_556 ? C10 C11 C1 115.04(11) . 3_556 ? C11 C12 C19 122.09(12) . . ? C11 C12 C13 121.49(12) . . ? C19 C12 C13 116.41(11) . . ? C14 C13 C18 118.30(14) . . ? C14 C13 C12 122.62(13) . . ? C18 C13 C12 119.07(14) . . ? C15 C14 C13 120.40(16) . . ? C16 C15 C14 120.78(18) . . ? C15 C16 C17 119.68(16) . . ? C16 C17 C18 120.11(18) . . ? C17 C18 C13 120.71(18) . . ? C24 C19 C20 118.21(14) . . ? C24 C19 C12 122.77(13) . . ? C20 C19 C12 119.02(14) . . ? C21 C20 C19 120.75(16) . . ? C22 C21 C20 120.31(16) . . ? C23 C22 C21 119.77(15) . . ? C22 C23 C24 120.23(16) . . ? C23 C24 C19 120.71(15) . . ? 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 C11 C1 C2 C3 150(10) 3_556 . . . ? C1 C2 C3 C4 18.8(17) . . . . ? C1 C2 C3 C8 -160.3(16) . . . . ? C8 C3 C4 C5 0.4(2) . . . . ? C2 C3 C4 C5 -178.74(13) . . . . ? C3 C4 C5 C6 0.7(2) . . . . ? C4 C5 C6 C7 -1.1(2) . . . . ? C5 C6 C7 C8 0.3(2) . . . . ? C6 C7 C8 C3 0.8(2) . . . . ? C6 C7 C8 C9 -176.97(13) . . . . ? C4 C3 C8 C7 -1.11(19) . . . . ? C2 C3 C8 C7 178.01(12) . . . . ? C4 C3 C8 C9 176.62(12) . . . . ? C2 C3 C8 C9 -4.26(19) . . . . ? C7 C8 C9 C10 72.7(15) . . . . ? C3 C8 C9 C10 -105.0(15) . . . . ? C8 C9 C10 C11 60(3) . . . . ? C9 C10 C11 C12 -121.9(17) . . . . ? C9 C10 C11 C1 55.2(17) . . . 3_556 ? C10 C11 C12 C19 177.77(13) . . . . ? C1 C11 C12 C19 0.9(2) 3_556 . . . ? C10 C11 C12 C13 -1.0(2) . . . . ? C1 C11 C12 C13 -177.81(13) 3_556 . . . ? C11 C12 C13 C14 51.0(2) . . . . ? C19 C12 C13 C14 -127.83(15) . . . . ? C11 C12 C13 C18 -129.92(16) . . . . ? C19 C12 C13 C18 51.29(19) . . . . ? C18 C13 C14 C15 -0.1(2) . . . . ? C12 C13 C14 C15 178.97(14) . . . . ? C13 C14 C15 C16 0.5(3) . . . . ? C14 C15 C16 C17 0.3(3) . . . . ? C15 C16 C17 C18 -1.5(3) . . . . ? C16 C17 C18 C13 1.9(3) . . . . ? C14 C13 C18 C17 -1.1(2) . . . . ? C12 C13 C18 C17 179.79(14) . . . . ? C11 C12 C19 C24 46.9(2) . . . . ? C13 C12 C19 C24 -134.29(14) . . . . ? C11 C12 C19 C20 -133.21(15) . . . . ? C13 C12 C19 C20 45.57(19) . . . . ? C24 C19 C20 C21 -1.0(2) . . . . ? C12 C19 C20 C21 179.15(15) . . . . ? C19 C20 C21 C22 1.3(3) . . . . ? C20 C21 C22 C23 -0.8(3) . . . . ? C21 C22 C23 C24 -0.1(2) . . . . ? C22 C23 C24 C19 0.4(2) . . . . ? C20 C19 C24 C23 0.1(2) . . . . ? C12 C19 C24 C23 180.00(13) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.225 _refine_diff_density_min -0.128 _refine_diff_density_rms 0.037 #===END data_3b _database_code_depnum_ccdc_archive 'CCDC 721526' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C48 H24, 0.5(C2 H2 Cl4)' _chemical_formula_sum 'C49 H25 Cl2' _chemical_formula_weight 684.59 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 15.983(4) _cell_length_b 19.880(4) _cell_length_c 21.062(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6692(3) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9687 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 24.01 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.359 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2824 _exptl_absorpt_coefficient_mu 0.231 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.9189 _exptl_absorpt_correction_T_max 0.9552 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 47774 _diffrn_reflns_av_R_equivalents 0.0580 _diffrn_reflns_av_sigmaI/netI 0.0282 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 25.75 _reflns_number_total 6393 _reflns_number_gt 4613 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0392P)^2^+3.0150P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6393 _refine_ls_number_parameters 460 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0636 _refine_ls_R_factor_gt 0.0400 _refine_ls_wR_factor_ref 0.1039 _refine_ls_wR_factor_gt 0.0911 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 C1 C 0.01197(12) 0.41354(9) 0.36252(8) 0.0334(4) Uani 1 1 d . . . C2 C 0.05638(12) 0.37053(10) 0.38402(8) 0.0340(4) Uani 1 1 d . . . C3 C 0.10579(11) 0.31543(9) 0.40596(8) 0.0337(4) Uani 1 1 d . . . C4 C 0.10087(12) 0.25294(10) 0.37523(9) 0.0399(5) Uani 1 1 d . . . H4 H 0.0641 0.2476 0.3401 0.048 Uiso 1 1 calc R . . C5 C 0.14828(13) 0.19938(10) 0.39506(10) 0.0440(5) Uani 1 1 d . . . H5 H 0.1443 0.1575 0.3735 0.053 Uiso 1 1 calc R . . C6 C 0.20168(13) 0.20604(10) 0.44605(10) 0.0440(5) Uani 1 1 d . . . H6 H 0.2344 0.1688 0.4596 0.053 Uiso 1 1 calc R . . C7 C 0.20754(12) 0.26672(10) 0.47730(10) 0.0407(5) Uani 1 1 d . . . H7 H 0.2439 0.2708 0.5128 0.049 Uiso 1 1 calc R . . C8 C 0.16093(11) 0.32245(9) 0.45772(9) 0.0331(4) Uani 1 1 d . . . C9 C 0.17178(11) 0.38589(10) 0.48835(9) 0.0331(4) Uani 1 1 d . . . C10 C 0.18692(11) 0.43798(9) 0.51440(8) 0.0322(4) Uani 1 1 d . . . C11 C 0.20092(11) 0.50209(9) 0.54353(8) 0.0313(4) Uani 1 1 d . . . C12 C 0.25920(11) 0.51229(9) 0.59008(8) 0.0320(4) Uani 1 1 d . . . C13 C 0.14980(11) 0.55499(9) 0.51865(9) 0.0327(4) Uani 1 1 d . . . C14 C 0.10699(12) 0.59789(9) 0.49523(9) 0.0338(4) Uani 1 1 d . . . C15 C 0.06023(11) 0.65381(9) 0.47168(9) 0.0327(4) Uani 1 1 d . . . C16 C 0.06961(12) 0.71692(10) 0.49991(9) 0.0392(5) Uani 1 1 d . . . H16 H 0.1067 0.7217 0.5348 0.047 Uiso 1 1 calc R . . C17 C 0.02652(13) 0.77218(10) 0.47845(10) 0.0435(5) Uani 1 1 d . . . H17 H 0.0339 0.8146 0.4985 0.052 Uiso 1 1 calc R . . C18 C -0.02766(13) 0.76588(10) 0.42759(10) 0.0450(5) Uani 1 1 d . . . H18 H -0.0572 0.8041 0.4124 0.054 Uiso 1 1 calc R . . C19 C -0.03866(13) 0.70400(10) 0.39899(10) 0.0411(5) Uani 1 1 d . . . H19 H -0.0762 0.7000 0.3642 0.049 Uiso 1 1 calc R . . C20 C 0.00439(11) 0.64720(9) 0.42030(9) 0.0331(4) Uani 1 1 d . . . C21 C -0.00917(11) 0.58320(10) 0.39095(9) 0.0346(4) Uani 1 1 d . . . C22 C -0.02508(11) 0.53069(10) 0.36583(8) 0.0340(4) Uani 1 1 d . . . C23 C -0.03971(11) 0.46628(10) 0.33789(8) 0.0334(4) Uani 1 1 d . . . C24 C -0.09687(11) 0.45554(10) 0.29044(8) 0.0356(4) Uani 1 1 d . . . C25 C 0.31891(11) 0.46221(9) 0.61566(8) 0.0331(4) Uani 1 1 d . . . C26 C 0.33294(13) 0.39490(10) 0.60181(9) 0.0409(5) Uani 1 1 d . . . H26 H 0.2993 0.3724 0.5713 0.049 Uiso 1 1 calc R . . C27 C 0.39653(13) 0.36093(11) 0.63296(10) 0.0469(5) Uani 1 1 d . . . H27 H 0.4061 0.3148 0.6237 0.056 Uiso 1 1 calc R . . C28 C 0.44643(14) 0.39311(11) 0.67746(10) 0.0487(5) Uani 1 1 d . . . H28 H 0.4900 0.3690 0.6981 0.058 Uiso 1 1 calc R . . C29 C 0.43309(13) 0.46004(11) 0.69190(10) 0.0455(5) Uani 1 1 d . . . H29 H 0.4671 0.4821 0.7225 0.055 Uiso 1 1 calc R . . C30 C 0.36948(11) 0.49458(10) 0.66120(9) 0.0355(4) Uani 1 1 d . . . C31 C 0.34309(11) 0.56484(10) 0.66669(8) 0.0347(4) Uani 1 1 d . . . C32 C 0.37196(13) 0.61563(10) 0.70564(9) 0.0415(5) Uani 1 1 d . . . H32 H 0.4164 0.6075 0.7346 0.050 Uiso 1 1 calc R . . C33 C 0.33518(13) 0.67849(11) 0.70187(9) 0.0440(5) Uani 1 1 d . . . H33 H 0.3542 0.7137 0.7287 0.053 Uiso 1 1 calc R . . C34 C 0.27104(13) 0.69047(10) 0.65944(9) 0.0422(5) Uani 1 1 d . . . H34 H 0.2470 0.7341 0.6569 0.051 Uiso 1 1 calc R . . C35 C 0.24110(12) 0.63947(10) 0.62027(9) 0.0390(5) Uani 1 1 d . . . H35 H 0.1965 0.6480 0.5916 0.047 Uiso 1 1 calc R . . C36 C 0.27714(11) 0.57596(9) 0.62362(8) 0.0325(4) Uani 1 1 d . . . C37 C -0.11143(12) 0.39169(11) 0.25583(9) 0.0399(5) Uani 1 1 d . . . C38 C -0.07907(13) 0.32747(11) 0.26324(10) 0.0473(5) Uani 1 1 d . . . H38 H -0.0403 0.3182 0.2963 0.057 Uiso 1 1 calc R . . C39 C -0.10390(15) 0.27672(13) 0.22187(11) 0.0571(6) Uani 1 1 d . . . H39 H -0.0818 0.2327 0.2268 0.068 Uiso 1 1 calc R . . C40 C -0.16014(16) 0.28969(14) 0.17390(11) 0.0647(7) Uani 1 1 d . . . H40 H -0.1759 0.2546 0.1457 0.078 Uiso 1 1 calc R . . C41 C -0.19371(15) 0.35281(15) 0.16636(11) 0.0616(7) Uani 1 1 d . . . H41 H -0.2325 0.3614 0.1332 0.074 Uiso 1 1 calc R . . C42 C -0.17043(13) 0.40411(12) 0.20765(9) 0.0463(5) Uani 1 1 d . . . C43 C -0.19709(13) 0.47423(12) 0.21125(9) 0.0470(5) Uani 1 1 d . . . C44 C -0.25606(14) 0.50928(14) 0.17631(11) 0.0602(7) Uani 1 1 d . . . H44 H -0.2852 0.4879 0.1425 0.072 Uiso 1 1 calc R . . C45 C -0.27203(15) 0.57573(15) 0.19120(12) 0.0638(7) Uani 1 1 d . . . H45 H -0.3127 0.6001 0.1677 0.077 Uiso 1 1 calc R . . C46 C -0.22935(14) 0.60715(13) 0.24005(11) 0.0552(6) Uani 1 1 d . . . H46 H -0.2410 0.6529 0.2496 0.066 Uiso 1 1 calc R . . C47 C -0.16964(13) 0.57280(11) 0.27536(10) 0.0469(5) Uani 1 1 d . . . H47 H -0.1405 0.5948 0.3087 0.056 Uiso 1 1 calc R . . C48 C -0.15312(12) 0.50580(11) 0.26125(9) 0.0397(5) Uani 1 1 d . . . Cl1S Cl 0.56731(5) 0.55473(3) 0.57144(3) 0.0699(2) Uani 1 1 d . . . Cl2S Cl 0.59611(4) 0.42672(3) 0.51161(3) 0.06271(19) Uani 1 1 d . . . C1S C 0.52003(14) 0.48768(10) 0.52985(10) 0.0480(5) Uani 1 1 d . . . H1S H 0.4762 0.4668 0.5574 0.058 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 C1 0.0331(10) 0.0398(11) 0.0273(9) -0.0042(8) 0.0015(8) -0.0097(9) C2 0.0344(10) 0.0400(11) 0.0277(10) -0.0039(8) 0.0014(8) -0.0093(9) C3 0.0310(10) 0.0385(10) 0.0315(10) -0.0013(8) 0.0050(8) -0.0058(8) C4 0.0401(11) 0.0431(11) 0.0366(10) -0.0052(9) 0.0015(9) -0.0066(9) C5 0.0453(12) 0.0387(11) 0.0481(12) -0.0087(9) 0.0085(10) -0.0039(10) C6 0.0385(11) 0.0374(11) 0.0561(13) 0.0011(10) 0.0033(10) 0.0019(9) C7 0.0350(11) 0.0431(12) 0.0440(12) 0.0003(9) -0.0029(9) -0.0019(9) C8 0.0297(10) 0.0373(10) 0.0323(10) -0.0020(8) 0.0041(8) -0.0056(8) C9 0.0273(10) 0.0413(11) 0.0307(9) 0.0007(8) -0.0006(8) -0.0029(8) C10 0.0266(10) 0.0408(11) 0.0292(9) 0.0040(8) -0.0023(8) -0.0026(8) C11 0.0288(10) 0.0355(10) 0.0297(9) 0.0003(8) 0.0011(8) -0.0033(8) C12 0.0289(10) 0.0363(10) 0.0307(9) -0.0001(8) 0.0017(8) -0.0042(8) C13 0.0312(10) 0.0363(10) 0.0305(10) -0.0021(8) -0.0021(8) -0.0053(8) C14 0.0319(10) 0.0365(10) 0.0328(10) -0.0031(8) -0.0023(8) -0.0055(9) C15 0.0289(10) 0.0340(10) 0.0352(10) 0.0020(8) 0.0024(8) -0.0027(8) C16 0.0368(11) 0.0387(11) 0.0422(11) -0.0021(9) -0.0053(9) -0.0042(9) C17 0.0467(12) 0.0342(11) 0.0498(12) -0.0016(9) -0.0019(10) -0.0023(9) C18 0.0461(12) 0.0379(11) 0.0511(13) 0.0065(10) -0.0050(10) 0.0033(9) C19 0.0401(11) 0.0422(11) 0.0410(11) 0.0034(9) -0.0054(9) -0.0018(9) C20 0.0297(10) 0.0366(10) 0.0329(10) 0.0031(8) 0.0013(8) -0.0024(8) C21 0.0307(10) 0.0416(11) 0.0316(10) 0.0038(9) -0.0023(8) -0.0014(9) C22 0.0289(10) 0.0436(11) 0.0294(9) 0.0032(9) -0.0018(8) -0.0026(8) C23 0.0298(10) 0.0419(11) 0.0283(9) -0.0005(8) 0.0031(8) -0.0066(8) C24 0.0287(10) 0.0494(12) 0.0287(10) 0.0004(8) 0.0031(8) -0.0101(9) C25 0.0297(10) 0.0400(11) 0.0296(9) 0.0014(8) 0.0002(8) -0.0027(8) C26 0.0398(11) 0.0421(11) 0.0408(11) -0.0024(9) -0.0080(9) 0.0001(9) C27 0.0481(13) 0.0454(12) 0.0471(12) -0.0010(10) -0.0072(10) 0.0066(10) C28 0.0449(13) 0.0528(13) 0.0485(13) 0.0049(10) -0.0117(10) 0.0093(10) C29 0.0396(12) 0.0575(13) 0.0394(11) -0.0008(10) -0.0108(9) -0.0045(10) C30 0.0305(10) 0.0466(11) 0.0293(10) 0.0016(8) -0.0018(8) -0.0046(9) C31 0.0311(10) 0.0442(11) 0.0287(9) -0.0004(8) 0.0015(8) -0.0072(8) C32 0.0397(11) 0.0506(13) 0.0343(10) -0.0034(9) -0.0052(9) -0.0094(10) C33 0.0476(12) 0.0478(12) 0.0365(11) -0.0088(9) 0.0011(10) -0.0161(10) C34 0.0459(12) 0.0381(11) 0.0424(11) -0.0037(9) 0.0022(10) -0.0055(9) C35 0.0367(11) 0.0428(11) 0.0373(10) -0.0018(9) -0.0020(9) -0.0045(9) C36 0.0302(10) 0.0394(10) 0.0279(9) -0.0010(8) 0.0023(8) -0.0057(8) C37 0.0323(10) 0.0558(13) 0.0316(10) -0.0028(9) 0.0030(8) -0.0157(9) C38 0.0418(12) 0.0565(13) 0.0435(12) -0.0116(10) -0.0001(10) -0.0125(10) C39 0.0540(14) 0.0629(15) 0.0542(14) -0.0182(12) 0.0037(12) -0.0192(12) C40 0.0659(16) 0.0783(19) 0.0499(14) -0.0198(13) 0.0015(13) -0.0338(15) C41 0.0538(15) 0.094(2) 0.0372(12) -0.0034(13) -0.0079(11) -0.0344(14) C42 0.0378(12) 0.0681(15) 0.0330(11) 0.0010(10) -0.0005(9) -0.0217(11) C43 0.0333(11) 0.0746(16) 0.0333(11) 0.0100(10) -0.0024(9) -0.0174(11) C44 0.0440(13) 0.091(2) 0.0454(13) 0.0181(13) -0.0108(11) -0.0200(13) C45 0.0431(13) 0.091(2) 0.0572(15) 0.0306(14) -0.0101(12) -0.0049(14) C46 0.0426(13) 0.0693(15) 0.0536(14) 0.0210(12) -0.0008(11) -0.0007(11) C47 0.0367(12) 0.0618(14) 0.0422(12) 0.0086(10) -0.0023(9) -0.0048(10) C48 0.0299(10) 0.0591(13) 0.0302(10) 0.0094(9) 0.0004(8) -0.0101(9) Cl1S 0.0880(5) 0.0567(4) 0.0651(4) -0.0049(3) -0.0269(4) -0.0162(3) Cl2S 0.0502(3) 0.0534(3) 0.0845(5) 0.0133(3) 0.0078(3) 0.0130(3) C1S 0.0471(13) 0.0436(12) 0.0534(13) 0.0002(10) -0.0036(10) -0.0027(10) _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 C1 C2 1.200(3) . ? C1 C23 1.432(3) . ? C2 C3 1.427(3) . ? C3 C4 1.403(3) . ? C3 C8 1.409(3) . ? C4 C5 1.372(3) . ? C5 C6 1.378(3) . ? C6 C7 1.377(3) . ? C7 C8 1.397(3) . ? C8 C9 1.427(3) . ? C9 C10 1.197(3) . ? C10 C11 1.432(3) . ? C11 C12 1.367(2) . ? C11 C13 1.431(3) . ? C12 C36 1.477(2) . ? C12 C25 1.481(3) . ? C13 C14 1.199(3) . ? C14 C15 1.428(3) . ? C15 C16 1.396(3) . ? C15 C20 1.409(3) . ? C16 C17 1.373(3) . ? C17 C18 1.383(3) . ? C18 C19 1.381(3) . ? C19 C20 1.396(3) . ? C20 C21 1.431(3) . ? C21 C22 1.198(3) . ? C22 C23 1.428(3) . ? C23 C24 1.371(3) . ? C24 C48 1.478(3) . ? C24 C37 1.482(3) . ? C25 C26 1.388(3) . ? C25 C30 1.410(3) . ? C26 C27 1.386(3) . ? C27 C28 1.387(3) . ? C28 C29 1.381(3) . ? C29 C30 1.387(3) . ? C30 C31 1.464(3) . ? C31 C32 1.380(3) . ? C31 C36 1.408(3) . ? C32 C33 1.383(3) . ? C33 C34 1.381(3) . ? C34 C35 1.392(3) . ? C35 C36 1.390(3) . ? C37 C38 1.386(3) . ? C37 C42 1.407(3) . ? C38 C39 1.391(3) . ? C39 C40 1.377(3) . ? C40 C41 1.374(4) . ? C41 C42 1.391(3) . ? C42 C43 1.460(3) . ? C43 C44 1.384(3) . ? C43 C48 1.413(3) . ? C44 C45 1.382(4) . ? C45 C46 1.383(3) . ? C46 C47 1.389(3) . ? C47 C48 1.390(3) . ? Cl1S C1S 1.765(2) . ? Cl2S C1S 1.759(2) . ? C1S C1S 1.494(4) 5_666 ? 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 C1 C23 178.3(2) . . ? C1 C2 C3 175.08(19) . . ? C4 C3 C8 118.67(18) . . ? C4 C3 C2 119.95(17) . . ? C8 C3 C2 121.37(16) . . ? C5 C4 C3 121.05(19) . . ? C4 C5 C6 120.32(19) . . ? C7 C6 C5 119.91(19) . . ? C6 C7 C8 121.14(19) . . ? C7 C8 C3 118.91(17) . . ? C7 C8 C9 120.17(17) . . ? C3 C8 C9 120.88(17) . . ? C10 C9 C8 175.2(2) . . ? C9 C10 C11 176.5(2) . . ? C12 C11 C13 122.85(17) . . ? C12 C11 C10 123.07(17) . . ? C13 C11 C10 114.07(15) . . ? C11 C12 C36 127.01(17) . . ? C11 C12 C25 126.88(17) . . ? C36 C12 C25 106.09(15) . . ? C14 C13 C11 177.08(19) . . ? C13 C14 C15 174.03(19) . . ? C16 C15 C20 118.61(17) . . ? C16 C15 C14 119.68(17) . . ? C20 C15 C14 121.71(16) . . ? C17 C16 C15 121.65(18) . . ? C16 C17 C18 119.77(19) . . ? C19 C18 C17 119.88(19) . . ? C18 C19 C20 121.15(19) . . ? C19 C20 C15 118.93(17) . . ? C19 C20 C21 120.37(17) . . ? C15 C20 C21 120.70(16) . . ? C22 C21 C20 176.3(2) . . ? C21 C22 C23 176.4(2) . . ? C24 C23 C22 123.31(18) . . ? C24 C23 C1 122.31(17) . . ? C22 C23 C1 114.37(16) . . ? C23 C24 C48 127.11(18) . . ? C23 C24 C37 126.62(18) . . ? C48 C24 C37 106.20(16) . . ? C26 C25 C30 119.37(17) . . ? C26 C25 C12 132.53(17) . . ? C30 C25 C12 108.07(16) . . ? C27 C26 C25 119.27(18) . . ? C26 C27 C28 121.1(2) . . ? C29 C28 C27 120.28(19) . . ? C28 C29 C30 119.17(19) . . ? C29 C30 C25 120.77(18) . . ? C29 C30 C31 130.31(18) . . ? C25 C30 C31 108.91(16) . . ? C32 C31 C36 121.21(18) . . ? C32 C31 C30 130.44(18) . . ? C36 C31 C30 108.34(16) . . ? C31 C32 C33 118.99(19) . . ? C34 C33 C32 120.57(19) . . ? C33 C34 C35 120.9(2) . . ? C36 C35 C34 119.29(18) . . ? C35 C36 C31 119.05(17) . . ? C35 C36 C12 132.36(17) . . ? C31 C36 C12 108.58(16) . . ? C38 C37 C42 119.52(19) . . ? C38 C37 C24 132.45(18) . . ? C42 C37 C24 108.04(19) . . ? C37 C38 C39 119.4(2) . . ? C40 C39 C38 120.7(2) . . ? C41 C40 C39 120.7(2) . . ? C40 C41 C42 119.5(2) . . ? C41 C42 C37 120.1(2) . . ? C41 C42 C43 130.9(2) . . ? C37 C42 C43 109.00(18) . . ? C44 C43 C48 120.8(2) . . ? C44 C43 C42 130.7(2) . . ? C48 C43 C42 108.53(18) . . ? C45 C44 C43 119.1(2) . . ? C44 C45 C46 120.6(2) . . ? C45 C46 C47 121.0(2) . . ? C46 C47 C48 119.1(2) . . ? C47 C48 C43 119.36(19) . . ? C47 C48 C24 132.41(18) . . ? C43 C48 C24 108.20(19) . . ? C1S C1S Cl2S 109.8(2) 5_666 . ? C1S C1S Cl1S 110.7(2) 5_666 . ? Cl2S C1S Cl1S 109.44(12) . . ? 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 C23 C1 C2 C3 -173(100) . . . . ? C1 C2 C3 C4 7(2) . . . . ? C1 C2 C3 C8 -174(2) . . . . ? C8 C3 C4 C5 0.3(3) . . . . ? C2 C3 C4 C5 179.42(18) . . . . ? C3 C4 C5 C6 0.3(3) . . . . ? C4 C5 C6 C7 0.0(3) . . . . ? C5 C6 C7 C8 -0.9(3) . . . . ? C6 C7 C8 C3 1.4(3) . . . . ? C6 C7 C8 C9 -176.17(18) . . . . ? C4 C3 C8 C7 -1.1(3) . . . . ? C2 C3 C8 C7 179.77(17) . . . . ? C4 C3 C8 C9 176.46(17) . . . . ? C2 C3 C8 C9 -2.6(3) . . . . ? C7 C8 C9 C10 36(2) . . . . ? C3 C8 C9 C10 -141(2) . . . . ? C8 C9 C10 C11 151(3) . . . . ? C9 C10 C11 C12 175(100) . . . . ? C9 C10 C11 C13 -6(3) . . . . ? C13 C11 C12 C36 2.6(3) . . . . ? C10 C11 C12 C36 -178.87(17) . . . . ? C13 C11 C12 C25 -175.38(17) . . . . ? C10 C11 C12 C25 3.2(3) . . . . ? C12 C11 C13 C14 148(4) . . . . ? C10 C11 C13 C14 -31(4) . . . . ? C11 C13 C14 C15 -147(3) . . . . ? C13 C14 C15 C16 -5(2) . . . . ? C13 C14 C15 C20 175.3(19) . . . . ? C20 C15 C16 C17 -0.6(3) . . . . ? C14 C15 C16 C17 179.39(19) . . . . ? C15 C16 C17 C18 -0.1(3) . . . . ? C16 C17 C18 C19 0.5(3) . . . . ? C17 C18 C19 C20 -0.3(3) . . . . ? C18 C19 C20 C15 -0.4(3) . . . . ? C18 C19 C20 C21 178.65(19) . . . . ? C16 C15 C20 C19 0.8(3) . . . . ? C14 C15 C20 C19 -179.17(17) . . . . ? C16 C15 C20 C21 -178.22(17) . . . . ? C14 C15 C20 C21 1.8(3) . . . . ? C19 C20 C21 C22 -33(3) . . . . ? C15 C20 C21 C22 146(3) . . . . ? C20 C21 C22 C23 -158(3) . . . . ? C21 C22 C23 C24 -172(3) . . . . ? C21 C22 C23 C1 7(3) . . . . ? C2 C1 C23 C24 172(100) . . . . ? C2 C1 C23 C22 -7(7) . . . . ? C22 C23 C24 C48 -1.3(3) . . . . ? C1 C23 C24 C48 -179.80(17) . . . . ? C22 C23 C24 C37 175.23(17) . . . . ? C1 C23 C24 C37 -3.2(3) . . . . ? C11 C12 C25 C26 -0.3(3) . . . . ? C36 C12 C25 C26 -178.6(2) . . . . ? C11 C12 C25 C30 177.86(17) . . . . ? C36 C12 C25 C30 -0.45(19) . . . . ? C30 C25 C26 C27 -0.1(3) . . . . ? C12 C25 C26 C27 177.9(2) . . . . ? C25 C26 C27 C28 -0.3(3) . . . . ? C26 C27 C28 C29 0.4(3) . . . . ? C27 C28 C29 C30 -0.2(3) . . . . ? C28 C29 C30 C25 -0.1(3) . . . . ? C28 C29 C30 C31 -179.0(2) . . . . ? C26 C25 C30 C29 0.3(3) . . . . ? C12 C25 C30 C29 -178.15(17) . . . . ? C26 C25 C30 C31 179.36(17) . . . . ? C12 C25 C30 C31 0.9(2) . . . . ? C29 C30 C31 C32 -2.8(3) . . . . ? C25 C30 C31 C32 178.25(19) . . . . ? C29 C30 C31 C36 177.9(2) . . . . ? C25 C30 C31 C36 -1.0(2) . . . . ? C36 C31 C32 C33 -0.2(3) . . . . ? C30 C31 C32 C33 -179.36(19) . . . . ? C31 C32 C33 C34 -0.5(3) . . . . ? C32 C33 C34 C35 1.0(3) . . . . ? C33 C34 C35 C36 -0.7(3) . . . . ? C34 C35 C36 C31 0.1(3) . . . . ? C34 C35 C36 C12 178.80(18) . . . . ? C32 C31 C36 C35 0.4(3) . . . . ? C30 C31 C36 C35 179.75(16) . . . . ? C32 C31 C36 C12 -178.63(17) . . . . ? C30 C31 C36 C12 0.7(2) . . . . ? C11 C12 C36 C35 2.7(3) . . . . ? C25 C12 C36 C35 -179.03(19) . . . . ? C11 C12 C36 C31 -178.49(17) . . . . ? C25 C12 C36 C31 -0.19(19) . . . . ? C23 C24 C37 C38 5.2(3) . . . . ? C48 C24 C37 C38 -177.7(2) . . . . ? C23 C24 C37 C42 -175.17(18) . . . . ? C48 C24 C37 C42 2.0(2) . . . . ? C42 C37 C38 C39 1.6(3) . . . . ? C24 C37 C38 C39 -178.8(2) . . . . ? C37 C38 C39 C40 -0.1(3) . . . . ? C38 C39 C40 C41 -0.8(4) . . . . ? C39 C40 C41 C42 0.1(4) . . . . ? C40 C41 C42 C37 1.5(3) . . . . ? C40 C41 C42 C43 -178.7(2) . . . . ? C38 C37 C42 C41 -2.3(3) . . . . ? C24 C37 C42 C41 177.97(18) . . . . ? C38 C37 C42 C43 177.79(18) . . . . ? C24 C37 C42 C43 -1.9(2) . . . . ? C41 C42 C43 C44 3.2(4) . . . . ? C37 C42 C43 C44 -176.9(2) . . . . ? C41 C42 C43 C48 -178.8(2) . . . . ? C37 C42 C43 C48 1.1(2) . . . . ? C48 C43 C44 C45 -0.5(3) . . . . ? C42 C43 C44 C45 177.3(2) . . . . ? C43 C44 C45 C46 0.5(3) . . . . ? C44 C45 C46 C47 -0.1(3) . . . . ? C45 C46 C47 C48 -0.2(3) . . . . ? C46 C47 C48 C43 0.2(3) . . . . ? C46 C47 C48 C24 -177.60(19) . . . . ? C44 C43 C48 C47 0.1(3) . . . . ? C42 C43 C48 C47 -178.13(17) . . . . ? C44 C43 C48 C24 178.43(18) . . . . ? C42 C43 C48 C24 0.2(2) . . . . ? C23 C24 C48 C47 -6.2(3) . . . . ? C37 C24 C48 C47 176.7(2) . . . . ? C23 C24 C48 C43 175.82(18) . . . . ? C37 C24 C48 C43 -1.3(2) . . . . ? Cl1S C1S C1S Cl1S 180.0 . . 5_666 5_666 ? Cl1S C1S C1S Cl2S -59.1(3) . . 5_666 5_666 ? Cl2S C1S C1S Cl2S 180.0 . . 5_666 5_666 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.75 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.305 _refine_diff_density_min -0.359 _refine_diff_density_rms 0.038 #===END