# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_1143o _database_code_depnum_ccdc_archive 'CCDC 907253' #TrackingRef '1143o.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H30 O4 S2' _chemical_formula_weight 470.62 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' 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 21/n' 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 12.8645(3) _cell_length_b 6.0509(1) _cell_length_c 15.8520(4) _cell_angle_alpha 90.00 _cell_angle_beta 96.708(2) _cell_angle_gamma 90.00 _cell_volume 1225.50(5) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5158 _cell_measurement_theta_min 3.4564 _cell_measurement_theta_max 62.5246 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.275 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 500 _exptl_absorpt_coefficient_mu 2.205 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.38429 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.1399 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7561 _diffrn_reflns_av_R_equivalents 0.0221 _diffrn_reflns_av_sigmaI/netI 0.0217 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 4.19 _diffrn_reflns_theta_max 62.62 _reflns_number_total 1949 _reflns_number_gt 1778 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.' _computing_structure_solution 'SIR92 (Giacovazzo et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^ > 2\s(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^)+(0.0417P)^2^+0.3395P] 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 SHELXL _refine_ls_extinction_coef 0.0023(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1949 _refine_ls_number_parameters 186 _refine_ls_number_restraints 120 _refine_ls_R_factor_all 0.0309 _refine_ls_R_factor_gt 0.0263 _refine_ls_wR_factor_ref 0.0745 _refine_ls_wR_factor_gt 0.0732 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.034 _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 C1 C 0.2797(4) 0.1358(9) 1.1596(3) 0.0573(17) Uani 0.392(5) 1 d PDU A 1 H1A H 0.2912 0.2882 1.1794 0.086 Uiso 0.392(5) 1 calc PR A 1 H1B H 0.2677 0.0410 1.2076 0.086 Uiso 0.392(5) 1 calc PR A 1 H1C H 0.2185 0.1304 1.1166 0.086 Uiso 0.392(5) 1 calc PR A 1 C2 C 0.3744(4) 0.0558(14) 1.1215(4) 0.0508(15) Uani 0.392(5) 1 d PDU A 1 H2A H 0.3590 -0.0810 1.0881 0.061 Uiso 0.392(5) 1 calc PR A 1 H2B H 0.4338 0.0283 1.1658 0.061 Uiso 0.392(5) 1 calc PR A 1 C3 C 0.3986(15) 0.261(2) 1.0608(9) 0.042(2) Uani 0.392(5) 1 d PDU A 1 H3A H 0.3801 0.4036 1.0860 0.050 Uiso 0.392(5) 1 calc PR A 1 H3B H 0.4735 0.2644 1.0519 0.050 Uiso 0.392(5) 1 calc PR A 1 C4 C 0.3301(15) 0.219(3) 0.9778(8) 0.027(3) Uani 0.392(5) 1 d PDU A 1 H4A H 0.3225 0.0565 0.9714 0.032 Uiso 0.392(5) 1 calc PR A 1 H4B H 0.2597 0.2783 0.9840 0.032 Uiso 0.392(5) 1 calc PR A 1 C1A C 0.3631(3) -0.0641(7) 1.1414(2) 0.0599(11) Uani 0.608(5) 1 d PDU A 2 H1D H 0.3156 -0.1291 1.0952 0.090 Uiso 0.608(5) 1 calc PR A 2 H1E H 0.3423 -0.1116 1.1961 0.090 Uiso 0.608(5) 1 calc PR A 2 H1F H 0.4348 -0.1133 1.1368 0.090 Uiso 0.608(5) 1 calc PR A 2 C2A C 0.3578(3) 0.1874(7) 1.13527(19) 0.0411(9) Uani 0.608(5) 1 d PDU A 2 H2C H 0.4016 0.2561 1.1837 0.049 Uiso 0.608(5) 1 calc PR A 2 H2D H 0.2848 0.2394 1.1352 0.049 Uiso 0.608(5) 1 calc PR A 2 C3A C 0.4009(11) 0.248(2) 1.0481(6) 0.061(3) Uani 0.608(5) 1 d PDU A 2 H3C H 0.4202 0.4062 1.0483 0.073 Uiso 0.608(5) 1 calc PR A 2 H3D H 0.4646 0.1600 1.0424 0.073 Uiso 0.608(5) 1 calc PR A 2 C4A C 0.3194(10) 0.201(2) 0.9730(6) 0.036(2) Uani 0.608(5) 1 d PDU A 2 H4C H 0.3101 0.0399 0.9644 0.043 Uiso 0.608(5) 1 calc PR A 2 H4D H 0.2512 0.2669 0.9822 0.043 Uiso 0.608(5) 1 calc PR A 2 O1 O 0.36018(8) 0.30333(16) 0.89907(6) 0.0327(3) Uani 1 1 d DU . . C5 C 0.34060(10) 0.5193(2) 0.88489(9) 0.0274(3) Uani 1 1 d . A . O2 O 0.29966(8) 0.63827(17) 0.93245(6) 0.0346(3) Uani 1 1 d . . . C6 C 0.37294(10) 0.5916(2) 0.80362(9) 0.0262(3) Uani 1 1 d . . . C7 C 0.36586(10) 0.8012(2) 0.77132(9) 0.0285(3) Uani 1 1 d . A . H7 H 0.3403 0.9237 0.8002 0.034 Uiso 1 1 calc R . . C8 C 0.40065(11) 0.8157(2) 0.69042(9) 0.0287(3) Uani 1 1 d . . . H8 H 0.4015 0.9498 0.6593 0.034 Uiso 1 1 calc R A . C9 C 0.43311(10) 0.6176(2) 0.66109(9) 0.0249(3) Uani 1 1 d . A . S1 S 0.42265(3) 0.41146(5) 0.73453(2) 0.02844(14) Uani 1 1 d . A . C10 C 0.46960(10) 0.5621(2) 0.57854(8) 0.0235(3) Uani 1 1 d . . . C11 C 0.54862(10) 0.6830(2) 0.54536(8) 0.0249(3) Uani 1 1 d . . . C12 C 0.42333(10) 0.3833(2) 0.53283(8) 0.0252(3) Uani 1 1 d . . . H12 H 0.3701 0.3030 0.5563 0.030 Uiso 1 1 calc R . . C13 C 0.60478(12) 0.8750(2) 0.59123(9) 0.0327(3) Uani 1 1 d . . . H13A H 0.6713 0.9007 0.5683 0.049 Uiso 1 1 calc R A . H13B H 0.6184 0.8412 0.6520 0.049 Uiso 1 1 calc R . . H13C H 0.5611 1.0078 0.5832 0.049 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 0.064(3) 0.073(4) 0.035(3) 0.007(2) 0.008(2) -0.013(3) C2 0.048(3) 0.057(5) 0.045(3) 0.013(3) -0.006(2) -0.001(3) C3 0.038(5) 0.067(5) 0.019(4) 0.000(3) -0.002(3) -0.004(4) C4 0.027(4) 0.023(4) 0.031(4) -0.008(3) 0.010(3) -0.007(3) C1A 0.080(2) 0.052(3) 0.046(2) 0.0176(17) -0.0049(17) -0.0153(19) C2A 0.0437(19) 0.050(2) 0.0290(15) 0.0055(15) 0.0031(12) 0.0005(16) C3A 0.043(4) 0.110(6) 0.031(4) 0.019(4) 0.006(3) -0.021(4) C4A 0.042(4) 0.044(5) 0.022(3) 0.009(3) 0.004(2) -0.010(2) O1 0.0439(6) 0.0296(6) 0.0268(5) 0.0004(4) 0.0135(4) 0.0005(4) C5 0.0268(7) 0.0299(8) 0.0259(7) -0.0030(6) 0.0045(6) -0.0015(6) O2 0.0408(6) 0.0362(6) 0.0293(5) -0.0051(5) 0.0143(4) 0.0033(5) C6 0.0272(7) 0.0290(8) 0.0231(7) -0.0045(6) 0.0061(5) -0.0001(5) C7 0.0322(7) 0.0265(8) 0.0274(7) -0.0046(6) 0.0056(6) 0.0042(6) C8 0.0358(7) 0.0244(7) 0.0262(7) 0.0003(6) 0.0050(6) 0.0033(6) C9 0.0264(7) 0.0254(7) 0.0229(7) 0.0000(6) 0.0033(5) 0.0000(5) S1 0.0400(2) 0.0230(2) 0.0245(2) -0.00086(13) 0.01291(15) 0.00134(13) C10 0.0263(7) 0.0229(7) 0.0214(7) 0.0014(5) 0.0037(5) 0.0043(5) C11 0.0276(7) 0.0232(7) 0.0239(7) 0.0004(5) 0.0028(5) 0.0025(5) C12 0.0267(7) 0.0243(7) 0.0254(7) 0.0024(6) 0.0063(5) -0.0010(5) C13 0.0370(8) 0.0318(8) 0.0304(8) -0.0053(6) 0.0085(6) -0.0070(6) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.502(8) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.624(12) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.518(12) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 O1 1.443(11) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C1A C2A 1.526(5) . ? C1A H1D 0.9800 . ? C1A H1E 0.9800 . ? C1A H1F 0.9800 . ? C2A C3A 1.591(8) . ? C2A H2C 0.9900 . ? C2A H2D 0.9900 . ? C3A C4A 1.518(9) . ? C3A H3C 0.9900 . ? C3A H3D 0.9900 . ? C4A O1 1.475(7) . ? C4A H4C 0.9900 . ? C4A H4D 0.9900 . ? O1 C5 1.3445(18) . ? C5 O2 1.2071(17) . ? C5 C6 1.4662(19) . ? C6 C7 1.367(2) . ? C6 S1 1.7207(13) . ? C7 C8 1.410(2) . ? C7 H7 0.9500 . ? C8 C9 1.3686(19) . ? C8 H8 0.9500 . ? C9 C10 1.4794(18) . ? C9 S1 1.7220(13) . ? C10 C12 1.3964(19) . ? C10 C11 1.4037(19) . ? C11 C12 1.3899(19) 3_666 ? C11 C13 1.5090(19) . ? C12 C11 1.3899(19) 3_666 ? C12 H12 0.9500 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? 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 C1 C2 C3 102.2(9) . . ? C1 C2 H2A 111.3 . . ? C3 C2 H2A 111.3 . . ? C1 C2 H2B 111.3 . . ? C3 C2 H2B 111.3 . . ? H2A C2 H2B 109.2 . . ? C4 C3 C2 104.6(10) . . ? C4 C3 H3A 110.8 . . ? C2 C3 H3A 110.8 . . ? C4 C3 H3B 110.8 . . ? C2 C3 H3B 110.8 . . ? H3A C3 H3B 108.9 . . ? O1 C4 C3 120.2(12) . . ? O1 C4 H4A 107.3 . . ? C3 C4 H4A 107.3 . . ? O1 C4 H4B 107.3 . . ? C3 C4 H4B 107.3 . . ? H4A C4 H4B 106.9 . . ? C2A C1A H1D 109.5 . . ? C2A C1A H1E 109.5 . . ? H1D C1A H1E 109.5 . . ? C2A C1A H1F 109.5 . . ? H1D C1A H1F 109.5 . . ? H1E C1A H1F 109.5 . . ? C1A C2A C3A 105.5(5) . . ? C1A C2A H2C 110.7 . . ? C3A C2A H2C 110.7 . . ? C1A C2A H2D 110.7 . . ? C3A C2A H2D 110.7 . . ? H2C C2A H2D 108.8 . . ? C4A C3A C2A 111.1(7) . . ? C4A C3A H3C 109.4 . . ? C2A C3A H3C 109.4 . . ? C4A C3A H3D 109.4 . . ? C2A C3A H3D 109.4 . . ? H3C C3A H3D 108.0 . . ? O1 C4A C3A 105.5(8) . . ? O1 C4A H4C 110.6 . . ? C3A C4A H4C 110.6 . . ? O1 C4A H4D 110.6 . . ? C3A C4A H4D 110.6 . . ? H4C C4A H4D 108.8 . . ? C5 O1 C4 115.2(7) . . ? C5 O1 C4A 117.6(6) . . ? C4 O1 C4A 7.1(13) . . ? O2 C5 O1 124.21(13) . . ? O2 C5 C6 124.04(13) . . ? O1 C5 C6 111.73(11) . . ? C7 C6 C5 126.37(12) . . ? C7 C6 S1 111.28(10) . . ? C5 C6 S1 122.33(10) . . ? C6 C7 C8 112.59(12) . . ? C6 C7 H7 123.7 . . ? C8 C7 H7 123.7 . . ? C9 C8 C7 113.37(13) . . ? C9 C8 H8 123.3 . . ? C7 C8 H8 123.3 . . ? C8 C9 C10 129.79(12) . . ? C8 C9 S1 110.71(10) . . ? C10 C9 S1 119.45(10) . . ? C6 S1 C9 92.05(7) . . ? C12 C10 C11 119.54(12) . . ? C12 C10 C9 118.34(12) . . ? C11 C10 C9 122.12(12) . . ? C12 C11 C10 117.29(12) 3_666 . ? C12 C11 C13 119.50(12) 3_666 . ? C10 C11 C13 123.20(12) . . ? C11 C12 C10 123.18(12) 3_666 . ? C11 C12 H12 118.4 3_666 . ? C10 C12 H12 118.4 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 62.62 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.264 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.045 data_1179o _database_code_depnum_ccdc_archive 'CCDC 907254' #TrackingRef '1179o.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H26 O4 S2' _chemical_formula_weight 442.57 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' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.5601(5) _cell_length_b 11.8606(9) _cell_length_c 12.1527(6) _cell_angle_alpha 110.052(6) _cell_angle_beta 90.591(5) _cell_angle_gamma 108.776(6) _cell_volume 1087.22(14) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4041 _cell_measurement_theta_min 3.9051 _cell_measurement_theta_max 62.5597 _exptl_crystal_description 'transparent plate' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.352 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 2.452 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.65446 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.1399 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6517 _diffrn_reflns_av_R_equivalents 0.0226 _diffrn_reflns_av_sigmaI/netI 0.0247 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.91 _diffrn_reflns_theta_max 62.65 _reflns_number_total 3424 _reflns_number_gt 2908 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.' _computing_structure_solution 'SIR92 (Giacovazzo et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^ > 2\s(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^)+(0.0754P)^2^+0.0013P] 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 3424 _refine_ls_number_parameters 273 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0416 _refine_ls_R_factor_gt 0.0362 _refine_ls_wR_factor_ref 0.1073 _refine_ls_wR_factor_gt 0.1044 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _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 2.2940(2) 0.3526(2) 0.98918(19) 0.0468(5) Uani 1 1 d . . . H1A H 2.2346 0.3517 1.0575 0.070 Uiso 1 1 calc R . . H1B H 2.4137 0.3966 1.0162 0.070 Uiso 1 1 calc R . . H1C H 2.2740 0.2645 0.9357 0.070 Uiso 1 1 calc R . . C2 C 2.2315(2) 0.42245(18) 0.92402(16) 0.0373(4) Uani 1 1 d . . . H2A H 2.2504 0.5110 0.9787 0.045 Uiso 1 1 calc R . . H2B H 2.2962 0.4273 0.8577 0.045 Uiso 1 1 calc R . . C3 C 2.0480(2) 0.35625(17) 0.87619(15) 0.0336(4) Uani 1 1 d . . . H3A H 2.0291 0.2675 0.8221 0.040 Uiso 1 1 calc R . . H3B H 1.9833 0.3520 0.9426 0.040 Uiso 1 1 calc R . . C4 C 1.9858(2) 0.42444(16) 0.81083(15) 0.0313(4) Uani 1 1 d . . . H4A H 2.0084 0.5146 0.8627 0.038 Uiso 1 1 calc R . . H4B H 2.0429 0.4234 0.7403 0.038 Uiso 1 1 calc R . . C5 C 1.7322(2) 0.40684(16) 0.71575(14) 0.0302(4) Uani 1 1 d . . . C6 C 1.5533(2) 0.33261(16) 0.68159(14) 0.0299(4) Uani 1 1 d . . . C7 C 1.4556(2) 0.22710(16) 0.70120(15) 0.0323(4) Uani 1 1 d . . . H7 H 1.4967 0.1856 0.7429 0.039 Uiso 1 1 calc R . . C8 C 1.2883(2) 0.18603(16) 0.65355(15) 0.0319(4) Uani 1 1 d . . . H8 H 1.2043 0.1143 0.6602 0.038 Uiso 1 1 calc R . . C9 C 1.2581(2) 0.26060(16) 0.59583(14) 0.0288(4) Uani 1 1 d . . . C10 C 1.1007(2) 0.24845(15) 0.53618(13) 0.0276(4) Uani 1 1 d . . . C11 C 0.9499(2) 0.16107(16) 0.54365(14) 0.0310(4) Uani 1 1 d . . . H11 H 0.9500 0.1070 0.5860 0.037 Uiso 1 1 calc R . . C12 C 0.8010(2) 0.15219(16) 0.49055(14) 0.0305(4) Uani 1 1 d . . . H12 H 0.7001 0.0921 0.4968 0.037 Uiso 1 1 calc R . . C13 C 0.7965(2) 0.23072(15) 0.42740(13) 0.0276(4) Uani 1 1 d . . . C14 C 0.9472(2) 0.31765(16) 0.41992(14) 0.0310(4) Uani 1 1 d . . . H14 H 0.9472 0.3717 0.3776 0.037 Uiso 1 1 calc R . . C15 C 1.0959(2) 0.32658(17) 0.47270(14) 0.0313(4) Uani 1 1 d . . . H15 H 1.1967 0.3865 0.4661 0.038 Uiso 1 1 calc R . . C16 C 0.6395(2) 0.22136(15) 0.36902(14) 0.0289(4) Uani 1 1 d . . . C17 C 0.6109(2) 0.30415(16) 0.32165(15) 0.0329(4) Uani 1 1 d . . . H17 H 0.6948 0.3802 0.3230 0.040 Uiso 1 1 calc R . . C18 C 0.4447(2) 0.26478(16) 0.27098(15) 0.0324(4) Uani 1 1 d . . . H18 H 0.4048 0.3114 0.2347 0.039 Uiso 1 1 calc R . . C19 C 0.3471(2) 0.15299(16) 0.27935(14) 0.0303(4) Uani 1 1 d . . . C20 C 0.1681(2) 0.08156(16) 0.23917(14) 0.0300(4) Uani 1 1 d . . . C21 C -0.0734(2) 0.07687(17) 0.13845(16) 0.0335(4) Uani 1 1 d . . . H21A H -0.1336 0.0750 0.2073 0.040 Uiso 1 1 calc R . . H21B H -0.1024 -0.0119 0.0811 0.040 Uiso 1 1 calc R . . C22 C -0.1200(2) 0.15886(18) 0.08153(16) 0.0361(4) Uani 1 1 d . . . H22A H -0.0562 0.1622 0.0145 0.043 Uiso 1 1 calc R . . H22B H -0.0904 0.2472 0.1399 0.043 Uiso 1 1 calc R . . C23 C -0.3049(2) 0.10560(17) 0.03726(16) 0.0366(4) Uani 1 1 d . . . H23A H -0.3681 0.0990 0.1040 0.044 Uiso 1 1 calc R . . H23B H -0.3332 0.0183 -0.0228 0.044 Uiso 1 1 calc R . . C24 C -0.3582(3) 0.1879(2) -0.0167(2) 0.0555(6) Uani 1 1 d . . . H24A H -0.3317 0.2743 0.0425 0.083 Uiso 1 1 calc R . . H24B H -0.4784 0.1501 -0.0431 0.083 Uiso 1 1 calc R . . H24C H -0.2988 0.1925 -0.0845 0.083 Uiso 1 1 calc R . . O1 O 1.80801(15) 0.35783(11) 0.77576(10) 0.0331(3) Uani 1 1 d . . . O2 O 1.80279(16) 0.50052(12) 0.69346(12) 0.0434(3) Uani 1 1 d . . . O3 O 0.10459(15) 0.13398(12) 0.17573(11) 0.0350(3) Uani 1 1 d . . . O4 O 0.08840(16) -0.01164(12) 0.25945(12) 0.0421(3) Uani 1 1 d . . . S1 S 1.43959(5) 0.38227(4) 0.60236(4) 0.03067(16) Uani 1 1 d . . . S2 S 0.45807(5) 0.09420(4) 0.35053(4) 0.03126(16) Uani 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 C1 0.0311(11) 0.0505(12) 0.0592(12) 0.0265(10) -0.0047(9) 0.0081(9) C2 0.0312(10) 0.0347(10) 0.0412(10) 0.0136(8) -0.0012(8) 0.0055(8) C3 0.0293(10) 0.0323(10) 0.0373(9) 0.0136(7) 0.0002(7) 0.0074(8) C4 0.0250(9) 0.0306(9) 0.0345(9) 0.0116(7) -0.0007(7) 0.0050(7) C5 0.0303(10) 0.0308(9) 0.0295(8) 0.0129(7) 0.0023(7) 0.0086(8) C6 0.0319(10) 0.0300(9) 0.0303(8) 0.0136(7) 0.0004(7) 0.0114(8) C7 0.0339(10) 0.0314(10) 0.0357(9) 0.0173(7) 0.0000(8) 0.0113(8) C8 0.0318(10) 0.0279(9) 0.0369(9) 0.0165(7) 0.0010(7) 0.0067(7) C9 0.0304(10) 0.0263(9) 0.0295(8) 0.0113(7) 0.0038(7) 0.0084(7) C10 0.0307(9) 0.0245(9) 0.0268(8) 0.0089(7) 0.0013(7) 0.0090(7) C11 0.0337(10) 0.0279(9) 0.0333(9) 0.0159(7) 0.0021(7) 0.0082(8) C12 0.0292(10) 0.0278(9) 0.0343(9) 0.0153(7) 0.0023(7) 0.0057(7) C13 0.0292(10) 0.0253(9) 0.0271(8) 0.0097(7) 0.0022(7) 0.0081(7) C14 0.0319(10) 0.0290(9) 0.0344(9) 0.0175(7) 0.0013(7) 0.0072(8) C15 0.0296(9) 0.0293(9) 0.0347(9) 0.0156(7) 0.0022(7) 0.0056(7) C16 0.0296(10) 0.0265(9) 0.0287(8) 0.0107(7) 0.0028(7) 0.0068(7) C17 0.0306(10) 0.0293(9) 0.0401(9) 0.0175(7) 0.0006(8) 0.0069(8) C18 0.0327(10) 0.0304(9) 0.0364(9) 0.0167(7) -0.0009(8) 0.0092(8) C19 0.0332(10) 0.0289(9) 0.0306(9) 0.0131(7) 0.0001(7) 0.0110(8) C20 0.0309(10) 0.0282(9) 0.0308(9) 0.0129(7) 0.0011(7) 0.0080(8) C21 0.0242(9) 0.0344(10) 0.0389(9) 0.0146(8) -0.0020(8) 0.0054(8) C22 0.0325(10) 0.0338(10) 0.0417(10) 0.0183(8) -0.0003(8) 0.0066(8) C23 0.0310(10) 0.0373(10) 0.0428(10) 0.0187(8) 0.0016(8) 0.0091(8) C24 0.0338(12) 0.0629(15) 0.0798(15) 0.0469(12) -0.0041(10) 0.0077(10) O1 0.0261(7) 0.0328(7) 0.0384(7) 0.0164(5) -0.0022(5) 0.0043(5) O2 0.0350(8) 0.0417(8) 0.0572(8) 0.0316(6) -0.0009(6) 0.0035(6) O3 0.0283(7) 0.0357(7) 0.0427(7) 0.0216(5) -0.0025(5) 0.0058(5) O4 0.0364(8) 0.0364(7) 0.0538(8) 0.0261(6) -0.0030(6) 0.0033(6) S1 0.0283(3) 0.0294(3) 0.0367(3) 0.01819(19) 0.00007(18) 0.00656(19) S2 0.0292(3) 0.0283(3) 0.0377(3) 0.01751(19) -0.00124(19) 0.0060(2) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.525(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.515(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.509(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 O1 1.451(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 O2 1.204(2) . ? C5 O1 1.347(2) . ? C5 C6 1.470(2) . ? C6 C7 1.363(2) . ? C6 S1 1.7203(17) . ? C7 C8 1.401(3) . ? C7 H7 0.9500 . ? C8 C9 1.382(2) . ? C8 H8 0.9500 . ? C9 C10 1.464(3) . ? C9 S1 1.7259(18) . ? C10 C11 1.398(2) . ? C10 C15 1.403(2) . ? C11 C12 1.379(2) . ? C11 H11 0.9500 . ? C12 C13 1.404(2) . ? C12 H12 0.9500 . ? C13 C14 1.395(2) . ? C13 C16 1.467(2) . ? C14 C15 1.375(3) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 C17 1.377(2) . ? C16 S2 1.7292(17) . ? C17 C18 1.406(3) . ? C17 H17 0.9500 . ? C18 C19 1.359(2) . ? C18 H18 0.9500 . ? C19 C20 1.473(2) . ? C19 S2 1.7205(17) . ? C20 O4 1.205(2) . ? C20 O3 1.347(2) . ? C21 O3 1.448(2) . ? C21 C22 1.513(2) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.516(3) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.520(3) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? 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 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 C1 112.10(15) . . ? C3 C2 H2A 109.2 . . ? C1 C2 H2A 109.2 . . ? C3 C2 H2B 109.2 . . ? C1 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? C4 C3 C2 112.32(15) . . ? C4 C3 H3A 109.1 . . ? C2 C3 H3A 109.1 . . ? C4 C3 H3B 109.1 . . ? C2 C3 H3B 109.1 . . ? H3A C3 H3B 107.9 . . ? O1 C4 C3 107.52(14) . . ? O1 C4 H4A 110.2 . . ? C3 C4 H4A 110.2 . . ? O1 C4 H4B 110.2 . . ? C3 C4 H4B 110.2 . . ? H4A C4 H4B 108.5 . . ? O2 C5 O1 123.90(16) . . ? O2 C5 C6 124.29(16) . . ? O1 C5 C6 111.81(14) . . ? C7 C6 C5 131.35(16) . . ? C7 C6 S1 111.35(13) . . ? C5 C6 S1 117.30(13) . . ? C6 C7 C8 113.15(15) . . ? C6 C7 H7 123.4 . . ? C8 C7 H7 123.4 . . ? C9 C8 C7 113.11(16) . . ? C9 C8 H8 123.4 . . ? C7 C8 H8 123.4 . . ? C8 C9 C10 129.05(16) . . ? C8 C9 S1 110.37(14) . . ? C10 C9 S1 120.58(13) . . ? C11 C10 C15 117.94(16) . . ? C11 C10 C9 120.91(15) . . ? C15 C10 C9 121.13(16) . . ? C12 C11 C10 121.01(16) . . ? C12 C11 H11 119.5 . . ? C10 C11 H11 119.5 . . ? C11 C12 C13 120.94(16) . . ? C11 C12 H12 119.5 . . ? C13 C12 H12 119.5 . . ? C14 C13 C12 117.90(16) . . ? C14 C13 C16 120.42(15) . . ? C12 C13 C16 121.67(15) . . ? C15 C14 C13 121.26(16) . . ? C15 C14 H14 119.4 . . ? C13 C14 H14 119.4 . . ? C14 C15 C10 120.95(17) . . ? C14 C15 H15 119.5 . . ? C10 C15 H15 119.5 . . ? C17 C16 C13 128.33(16) . . ? C17 C16 S2 110.41(13) . . ? C13 C16 S2 121.26(13) . . ? C16 C17 C18 113.21(16) . . ? C16 C17 H17 123.4 . . ? C18 C17 H17 123.4 . . ? C19 C18 C17 112.93(16) . . ? C19 C18 H18 123.5 . . ? C17 C18 H18 123.5 . . ? C18 C19 C20 129.63(16) . . ? C18 C19 S2 111.60(14) . . ? C20 C19 S2 118.76(13) . . ? O4 C20 O3 124.19(16) . . ? O4 C20 C19 124.95(16) . . ? O3 C20 C19 110.86(14) . . ? O3 C21 C22 106.72(14) . . ? O3 C21 H21A 110.4 . . ? C22 C21 H21A 110.4 . . ? O3 C21 H21B 110.4 . . ? C22 C21 H21B 110.4 . . ? H21A C21 H21B 108.6 . . ? C21 C22 C23 110.93(15) . . ? C21 C22 H22A 109.5 . . ? C23 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? C23 C22 H22B 109.5 . . ? H22A C22 H22B 108.0 . . ? C22 C23 C24 112.64(16) . . ? C22 C23 H23A 109.1 . . ? C24 C23 H23A 109.1 . . ? C22 C23 H23B 109.1 . . ? C24 C23 H23B 109.1 . . ? H23A C23 H23B 107.8 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C5 O1 C4 115.21(13) . . ? C20 O3 C21 115.70(13) . . ? C6 S1 C9 92.02(8) . . ? C19 S2 C16 91.85(8) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 62.65 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.350 _refine_diff_density_min -0.178 _refine_diff_density_rms 0.047