# Electronic Supplementary Material (ESI) for CrystEngComm # 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_compound3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H0 O2 S4' _chemical_formula_weight 292.35 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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/b 1 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, -y, -z' '-x-1/2, y-1/2, z' _cell_length_a 3.848(6) _cell_length_b 11.006(9) _cell_length_c 26.045(8) _cell_angle_alpha 99.47(3) _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1088.0(19) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 0.79 _cell_measurement_theta_max 31.10 _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.015 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.785 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.853 _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 150(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II 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 5626 _diffrn_reflns_av_R_equivalents 0.1442 _diffrn_reflns_av_sigmaI/netI 0.1905 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 0.79 _diffrn_reflns_theta_max 31.10 _reflns_number_total 2167 _reflns_number_gt 957 _reflns_threshold_expression >2\s(I) _computing_data_collection 'BRUKER APEX2 (Bruker, 2005)' _computing_cell_refinement 'BRUKER SMART (Bruker, 2005)' _computing_data_reduction 'BRUKER SAINT (Bruker, 2005)' _computing_structure_solution 'SIR 97 (Altomare et al, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP 3.2 (Farrugia, 1997) and Mercury 2.3' _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. The residual electron density present in the refinement is due to the isotropic refinement of all the atoms, specially the sulfur atoms, and also to the omission of the H atoms from the model. ISOR, SIMU and EADP restraints were unsuccessfully attempted and therefore an isotropic refinement was applied to all the atoms. Given the data quality, H atoms have been removed from the structure. Higher data completeness was precluded by partial dimerization of the compound. ; _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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens none _refine_ls_hydrogen_treatment none _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.044(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2167 _refine_ls_number_parameters 70 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2531 _refine_ls_R_factor_gt 0.1432 _refine_ls_wR_factor_ref 0.3774 _refine_ls_wR_factor_gt 0.3231 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _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 0.292(4) 0.0647(14) 0.4348(6) 0.026(4) Uiso 1 1 d . . . C2 C 0.126(3) 0.1193(12) 0.3859(5) 0.015(3) Uiso 1 1 d . . . C3 C -0.021(3) 0.2258(12) 0.3729(5) 0.015(3) Uiso 1 1 d . . . C4 C -0.008(3) 0.1349(12) 0.2902(5) 0.013(3) Uiso 1 1 d . . . C5 C -0.028(3) 0.1242(11) 0.2401(5) 0.013(3) Uiso 1 1 d . . . C6 C -0.071(3) 0.1608(12) 0.1398(5) 0.013(3) Uiso 1 1 d . . . C7 C 0.079(3) 0.0457(12) 0.1538(5) 0.011(3) Uiso 1 1 d . . . C8 C 0.190(3) -0.0159(12) 0.1150(5) 0.014(3) Uiso 1 1 d . . . C9 C 0.137(4) 0.0312(13) 0.0626(5) 0.018(3) Uiso 1 1 d . . . C10 C -0.027(4) 0.1455(13) 0.0500(5) 0.019(3) Uiso 1 1 d . . . C11 C -0.134(3) 0.2102(12) 0.0876(5) 0.014(3) Uiso 1 1 d . . . O1 O 0.424(2) -0.0338(9) 0.4425(4) 0.020(2) Uiso 1 1 d . . . O2 O 0.260(3) 0.1330(10) 0.4715(4) 0.027(3) Uiso 1 1 d . . . S1 S 0.1571(9) 0.0255(3) 0.33854(13) 0.0150(9) Uiso 1 1 d . . . S2 S -0.1710(9) 0.2675(3) 0.31202(13) 0.0150(9) Uiso 1 1 d . . . S3 S 0.1391(9) -0.0068(3) 0.21956(13) 0.0150(9) Uiso 1 1 d . . . S4 S -0.2076(9) 0.2324(3) 0.19138(13) 0.0150(9) Uiso 1 1 d . . . _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 O2 1.121(18) . ? C1 O1 1.242(17) . ? C1 C2 1.63(2) . ? C2 C3 1.393(19) . ? C2 S1 1.477(13) . ? C3 S2 1.816(14) . ? C4 C5 1.295(17) . ? C4 S2 1.604(13) . ? C4 S1 1.983(14) . ? C4 S3 2.279(13) . ? C5 S3 1.589(13) . ? C5 S4 2.000(13) . ? C6 C7 1.490(18) . ? C6 S4 1.534(13) . ? C6 C11 1.564(18) . ? C7 C8 1.198(17) . ? C7 S3 1.910(13) . ? C8 C9 1.550(19) . ? C9 C10 1.493(19) . ? C10 C11 1.185(18) . ? 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 C1 O1 112.9(15) . . ? O2 C1 C2 110.0(14) . . ? O1 C1 C2 136.9(14) . . ? C3 C2 S1 109.3(10) . . ? C3 C2 C1 141.6(12) . . ? S1 C2 C1 109.0(10) . . ? C2 C3 S2 133.2(10) . . ? C5 C4 S2 105.1(10) . . ? C5 C4 S1 134.1(10) . . ? S2 C4 S1 120.8(7) . . ? C5 C4 S3 42.6(7) . . ? S2 C4 S3 147.6(8) . . ? S1 C4 S3 91.5(5) . . ? C4 C5 S3 104.0(10) . . ? C4 C5 S4 134.1(10) . . ? S3 C5 S4 121.9(7) . . ? C7 C6 S4 104.7(9) . . ? C7 C6 C11 134.7(11) . . ? S4 C6 C11 120.4(10) . . ? C8 C7 C6 108.6(12) . . ? C8 C7 S3 120.0(11) . . ? C6 C7 S3 131.3(9) . . ? C7 C8 C9 118.0(12) . . ? C10 C9 C8 131.7(12) . . ? C11 C10 C9 112.2(13) . . ? C10 C11 C6 114.6(13) . . ? C2 S1 C4 95.2(6) . . ? C4 S2 C3 80.7(6) . . ? C5 S3 C7 82.0(6) . . ? C5 S3 C4 33.5(6) . . ? C7 S3 C4 115.3(5) . . ? C6 S4 C5 99.4(6) . . ? _diffrn_measured_fraction_theta_max 0.619 _diffrn_reflns_theta_full 31.10 _diffrn_measured_fraction_theta_full 0.619 _refine_diff_density_max 2.753 _refine_diff_density_min -2.387 _refine_diff_density_rms 0.431 _database_code_depnum_ccdc_archive 'CCDC 926913' ####################################################################### # # 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_compound4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common compound4 _chemical_melting_point ? _chemical_formula_moiety 'C22 H12 O4 S8, C4 H8 O' _chemical_formula_sum 'C26 H20 O5 S8' _chemical_formula_weight 668.98 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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 Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 43.192(4) _cell_length_b 6.091(3) _cell_length_c 23.009(6) _cell_angle_alpha 90.00 _cell_angle_beta 91.706(9) _cell_angle_gamma 90.00 _cell_volume 6051(3) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 0.94 _cell_measurement_theta_max 25.87 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.469 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2752 _exptl_absorpt_coefficient_mu 0.625 _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 150(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II 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 48694 _diffrn_reflns_av_R_equivalents 0.1000 _diffrn_reflns_av_sigmaI/netI 0.0663 _diffrn_reflns_limit_h_min -52 _diffrn_reflns_limit_h_max 52 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 0.94 _diffrn_reflns_theta_max 25.87 _reflns_number_total 5845 _reflns_number_gt 4186 _reflns_threshold_expression >2\s(I) _computing_data_collection 'BRUKER APEX2 (Bruker, 2005)' _computing_cell_refinement 'BRUKER SMART (Bruker, 2005)' _computing_data_reduction 'BRUKER SAINT (Bruker, 2005)' _computing_structure_solution 'SIR 97 (Altomare et al, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP 3.2 (Farrugia, 1997) and Mercury 2.3' _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^)+(0.0666P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5845 _refine_ls_number_parameters 357 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0809 _refine_ls_R_factor_gt 0.0514 _refine_ls_wR_factor_ref 0.1327 _refine_ls_wR_factor_gt 0.1225 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _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 S5 S 0.14896(2) 0.72064(15) 0.06825(4) 0.0217(2) Uani 1 1 d . . . S6 S 0.12431(2) 0.27156(15) 0.07198(5) 0.0253(2) Uani 1 1 d . . . S7 S 0.19601(2) 0.60969(16) 0.17552(4) 0.0262(2) Uani 1 1 d . . . S4 S 0.09041(2) 0.83966(15) 0.15798(4) 0.0225(2) Uani 1 1 d . . . S3 S 0.06181(2) 0.40231(15) 0.14501(4) 0.0223(2) Uani 1 1 d . . . S2 S 0.12616(2) 0.69160(16) 0.27414(4) 0.0258(2) Uani 1 1 d . . . S8 S 0.16819(2) 0.16801(16) 0.18568(5) 0.0298(3) Uani 1 1 d . . . S1 S 0.09357(2) 0.26343(16) 0.27111(4) 0.0248(2) Uani 1 1 d . . . O1 O 0.02289(6) 0.6895(4) 0.02853(11) 0.0257(6) Uani 1 1 d . . . O2 O 0.02887(7) 0.3245(4) 0.03339(12) 0.0252(7) Uani 1 1 d . . . O4 O 0.08956(7) 0.1800(4) -0.03138(12) 0.0355(7) Uani 1 1 d . . . H11 H 0.0804 0.1481 -0.0619 0.053 Uiso 1 1 calc R . . O3 O 0.07524(6) 0.5205(5) -0.05578(12) 0.0326(7) Uani 1 1 d . . . O5 O 0.05791(8) 0.9232(6) 0.37325(14) 0.0502(9) Uani 1 1 d . . . C5 C 0.12107(8) 0.3022(6) 0.32769(15) 0.0203(8) Uani 1 1 d . . . C9 C 0.08270(8) 0.7693(6) 0.08294(15) 0.0181(8) Uani 1 1 d . . . H15 H 0.0694 0.8799 0.0640 0.022 Uiso 1 1 calc R . . C3 C 0.15738(9) 0.5541(7) 0.37404(17) 0.0276(9) Uani 1 1 d . . . H16 H 0.1675 0.6890 0.3754 0.033 Uiso 1 1 calc R . . C13 C 0.09748(8) 0.4643(6) 0.03877(16) 0.0197(8) Uani 1 1 d . . . C7 C 0.10121(8) 0.5119(6) 0.23606(16) 0.0205(8) Uani 1 1 d . . . C1 C 0.14907(9) 0.1958(7) 0.41417(16) 0.0275(9) Uani 1 1 d . . . H19 H 0.1538 0.0916 0.4426 0.033 Uiso 1 1 calc R . . C15 C 0.14845(8) 0.4704(6) 0.10564(16) 0.0199(8) Uani 1 1 d . . . C12 C 0.10946(8) 0.7038(6) 0.04311(16) 0.0186(8) Uani 1 1 d . . . H21 H 0.1069 0.7768 0.0053 0.022 Uiso 1 1 calc R . . C18 C 0.20649(8) 0.4598(6) 0.23826(17) 0.0250(9) Uani 1 1 d . . . C2 C 0.16356(9) 0.3967(7) 0.41642(17) 0.0317(10) Uani 1 1 d . . . H23 H 0.1777 0.4275 0.4467 0.038 Uiso 1 1 calc R . . C4 C 0.13593(8) 0.5074(6) 0.32960(16) 0.0227(8) Uani 1 1 d . . . C6 C 0.12778(9) 0.1462(6) 0.37064(16) 0.0245(9) Uani 1 1 d . . . H25 H 0.1180 0.0103 0.3698 0.029 Uiso 1 1 calc R . . C8 C 0.08746(8) 0.5715(6) 0.18518(16) 0.0199(8) Uani 1 1 d . . . C19 C 0.22749(9) 0.5348(7) 0.28041(18) 0.0317(10) Uani 1 1 d . . . H27 H 0.2365 0.6727 0.2772 0.038 Uiso 1 1 calc R . . C10 C 0.06818(8) 0.5365(6) 0.07622(15) 0.0180(8) Uani 1 1 d . . . C11 C 0.03763(8) 0.5278(6) 0.04331(16) 0.0194(8) Uani 1 1 d . . . C14 C 0.08693(9) 0.3906(7) -0.02193(17) 0.0279(9) Uani 1 1 d . . . C16 C 0.16737(8) 0.4245(6) 0.15104(17) 0.0235(9) Uani 1 1 d . . . C17 C 0.19339(8) 0.2506(6) 0.24261(17) 0.0233(9) Uani 1 1 d . . . C20 C 0.23477(10) 0.4005(8) 0.32740(19) 0.0399(11) Uani 1 1 d . . . H33 H 0.2489 0.4487 0.3560 0.048 Uiso 1 1 calc R . . C22 C 0.20092(9) 0.1187(7) 0.29032(18) 0.0331(10) Uani 1 1 d . . . H34 H 0.1922 -0.0203 0.2938 0.040 Uiso 1 1 calc R . . C21 C 0.22143(10) 0.1975(8) 0.33233(19) 0.0403(12) Uani 1 1 d . . . H35 H 0.2263 0.1112 0.3647 0.048 Uiso 1 1 calc R . . C23 C 0.04791(12) 0.7596(8) 0.3328(3) 0.0578(15) Uani 1 1 d . . . H36A H 0.0527 0.8036 0.2936 0.069 Uiso 1 1 calc R . . H36B H 0.0583 0.6215 0.3413 0.069 Uiso 1 1 calc R . . C26 C 0.03255(12) 1.0614(9) 0.3854(2) 0.0581(15) Uani 1 1 d . . . H38A H 0.0372 1.2121 0.3752 0.070 Uiso 1 1 calc R . . H38B H 0.0281 1.0557 0.4264 0.070 Uiso 1 1 calc R . . C25 C 0.00602(13) 0.9813(11) 0.3505(3) 0.080(2) Uani 1 1 d . . . H41A H 0.0032 1.0646 0.3148 0.096 Uiso 1 1 calc R . . H41B H -0.0129 0.9868 0.3721 0.096 Uiso 1 1 calc R . . C24 C 0.01602(14) 0.7363(11) 0.3379(3) 0.084(2) Uani 1 1 d . . . H42A H 0.0111 0.6394 0.3697 0.101 Uiso 1 1 calc R . . H42B H 0.0063 0.6815 0.3022 0.101 Uiso 1 1 calc R . . H12 H 0.0143(9) 0.302(7) 0.0193(17) 0.019(12) 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 S5 0.0199(5) 0.0180(5) 0.0267(5) 0.0047(4) -0.0069(4) -0.0033(4) S6 0.0227(5) 0.0136(5) 0.0389(6) 0.0004(4) -0.0105(4) 0.0011(4) S7 0.0245(5) 0.0211(5) 0.0325(6) 0.0044(4) -0.0106(4) -0.0019(4) S4 0.0318(5) 0.0137(5) 0.0216(5) -0.0002(4) -0.0054(4) -0.0017(4) S3 0.0277(5) 0.0177(5) 0.0210(5) 0.0038(4) -0.0054(4) -0.0062(4) S2 0.0356(6) 0.0200(5) 0.0212(5) 0.0013(4) -0.0083(4) -0.0054(4) S8 0.0297(6) 0.0193(5) 0.0395(6) 0.0090(4) -0.0119(5) -0.0011(4) S1 0.0338(6) 0.0199(5) 0.0203(5) 0.0025(4) -0.0065(4) -0.0046(4) O1 0.0253(15) 0.0193(14) 0.0320(16) 0.0012(12) -0.0113(12) 0.0002(12) O2 0.0216(16) 0.0188(15) 0.0343(17) 0.0020(12) -0.0145(13) -0.0057(12) O4 0.049(2) 0.0287(17) 0.0284(17) -0.0092(13) -0.0114(14) -0.0016(14) O3 0.0387(17) 0.0330(17) 0.0252(16) 0.0017(13) -0.0139(13) -0.0026(14) O5 0.052(2) 0.056(2) 0.041(2) 0.0072(17) -0.0143(16) 0.0096(17) C5 0.023(2) 0.022(2) 0.0164(19) -0.0007(15) 0.0002(15) 0.0022(16) C9 0.0216(19) 0.0150(18) 0.0174(19) 0.0022(15) -0.0058(15) -0.0015(15) C3 0.030(2) 0.027(2) 0.026(2) -0.0040(17) -0.0034(18) -0.0016(17) C13 0.023(2) 0.0152(19) 0.021(2) 0.0001(15) -0.0045(16) -0.0029(15) C7 0.024(2) 0.0162(19) 0.021(2) 0.0009(15) 0.0003(16) 0.0002(15) C1 0.030(2) 0.035(2) 0.017(2) 0.0029(17) -0.0027(17) 0.0044(19) C15 0.0173(19) 0.0164(19) 0.026(2) 0.0012(16) -0.0043(16) -0.0014(15) C12 0.0218(19) 0.0135(19) 0.0204(19) 0.0052(15) -0.0039(15) -0.0013(15) C18 0.019(2) 0.030(2) 0.026(2) 0.0000(17) -0.0029(16) 0.0065(17) C2 0.027(2) 0.044(3) 0.023(2) 0.0021(19) -0.0106(18) 0.002(2) C4 0.026(2) 0.021(2) 0.021(2) -0.0011(16) -0.0004(16) 0.0060(17) C6 0.033(2) 0.023(2) 0.017(2) -0.0023(16) 0.0047(17) 0.0016(17) C8 0.0204(19) 0.0185(19) 0.021(2) -0.0018(16) -0.0028(16) -0.0030(15) C19 0.024(2) 0.039(3) 0.032(2) -0.005(2) -0.0098(18) 0.0033(19) C10 0.0228(19) 0.0128(18) 0.0180(19) 0.0010(15) -0.0055(15) -0.0043(15) C11 0.0194(19) 0.018(2) 0.020(2) 0.0017(16) -0.0050(15) -0.0031(16) C14 0.027(2) 0.032(2) 0.025(2) -0.0117(19) 0.0026(18) -0.0103(19) C16 0.022(2) 0.018(2) 0.030(2) -0.0021(17) -0.0024(17) -0.0018(16) C17 0.0157(18) 0.027(2) 0.027(2) 0.0031(17) -0.0008(16) 0.0040(16) C20 0.029(2) 0.060(3) 0.030(3) 0.000(2) -0.0078(19) 0.013(2) C22 0.026(2) 0.040(3) 0.034(2) 0.011(2) 0.0041(19) 0.0116(19) C21 0.035(3) 0.060(3) 0.025(2) 0.014(2) -0.001(2) 0.016(2) C23 0.060(4) 0.034(3) 0.079(4) -0.006(3) 0.004(3) 0.008(3) C26 0.062(4) 0.050(3) 0.063(4) -0.022(3) -0.001(3) 0.009(3) C25 0.045(3) 0.108(6) 0.086(5) -0.011(4) -0.010(3) 0.042(4) C24 0.070(4) 0.082(5) 0.101(6) -0.036(4) -0.001(4) -0.023(4) _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 S5 C15 1.751(4) . ? S5 C12 1.788(3) . ? S6 C15 1.762(4) . ? S6 C13 1.804(4) . ? S7 C16 1.754(4) . ? S7 C18 1.756(4) . ? S4 C8 1.755(4) . ? S4 C9 1.800(4) . ? S3 C8 1.756(4) . ? S3 C10 1.810(4) . ? S2 C4 1.742(4) . ? S2 C7 1.752(4) . ? S8 C17 1.752(4) . ? S8 C16 1.754(4) . ? S1 C7 1.751(4) . ? S1 C5 1.752(4) . ? O1 C11 1.216(4) . ? O2 C11 1.312(4) . ? O4 C14 1.306(5) . ? O3 C14 1.210(5) . ? O5 C26 1.416(6) . ? O5 C23 1.422(6) . ? C5 C6 1.395(5) . ? C5 C4 1.405(5) . ? C9 C12 1.549(5) . ? C9 C10 1.556(5) . ? C3 C2 1.388(6) . ? C3 C4 1.389(5) . ? C13 C14 1.524(5) . ? C13 C12 1.550(5) . ? C13 C10 1.613(5) . ? C7 C8 1.347(5) . ? C1 C6 1.373(5) . ? C1 C2 1.375(6) . ? C15 C16 1.336(5) . ? C18 C19 1.385(5) . ? C18 C17 1.399(5) . ? C19 C20 1.384(6) . ? C10 C11 1.503(5) . ? C17 C22 1.391(5) . ? C20 C21 1.371(7) . ? C22 C21 1.378(6) . ? C23 C24 1.393(7) . ? C26 C25 1.463(7) . ? C25 C24 1.583(8) . ? 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 C15 S5 C12 94.77(16) . . ? C15 S6 C13 95.91(17) . . ? C16 S7 C18 95.27(18) . . ? C8 S4 C9 96.16(17) . . ? C8 S3 C10 94.90(17) . . ? C4 S2 C7 95.51(18) . . ? C17 S8 C16 95.03(18) . . ? C7 S1 C5 95.34(17) . . ? C26 O5 C23 108.9(4) . . ? C6 C5 C4 119.9(3) . . ? C6 C5 S1 123.8(3) . . ? C4 C5 S1 116.2(3) . . ? C12 C9 C10 90.7(3) . . ? C12 C9 S4 120.6(2) . . ? C10 C9 S4 112.0(2) . . ? C2 C3 C4 119.1(4) . . ? C14 C13 C12 115.2(3) . . ? C14 C13 C10 110.6(3) . . ? C12 C13 C10 88.6(3) . . ? C14 C13 S6 111.5(3) . . ? C12 C13 S6 112.1(2) . . ? C10 C13 S6 117.1(2) . . ? C8 C7 S1 123.3(3) . . ? C8 C7 S2 121.0(3) . . ? S1 C7 S2 115.5(2) . . ? C6 C1 C2 121.2(4) . . ? C16 C15 S5 123.4(3) . . ? C16 C15 S6 122.7(3) . . ? S5 C15 S6 113.5(2) . . ? C9 C12 C13 91.6(3) . . ? C9 C12 S5 121.0(3) . . ? C13 C12 S5 112.8(2) . . ? C19 C18 C17 120.5(4) . . ? C19 C18 S7 123.5(3) . . ? C17 C18 S7 115.9(3) . . ? C1 C2 C3 120.7(4) . . ? C3 C4 C5 120.0(3) . . ? C3 C4 S2 123.3(3) . . ? C5 C4 S2 116.7(3) . . ? C1 C6 C5 119.2(4) . . ? C7 C8 S4 121.7(3) . . ? C7 C8 S3 123.7(3) . . ? S4 C8 S3 114.2(2) . . ? C20 C19 C18 118.7(4) . . ? C11 C10 C9 115.3(3) . . ? C11 C10 C13 114.3(3) . . ? C9 C10 C13 88.9(3) . . ? C11 C10 S3 105.7(2) . . ? C9 C10 S3 113.3(2) . . ? C13 C10 S3 119.1(2) . . ? O1 C11 O2 124.8(3) . . ? O1 C11 C10 123.8(3) . . ? O2 C11 C10 111.4(3) . . ? O3 C14 O4 124.9(4) . . ? O3 C14 C13 120.3(4) . . ? O4 C14 C13 114.6(4) . . ? C15 C16 S8 123.0(3) . . ? C15 C16 S7 121.7(3) . . ? S8 C16 S7 115.0(2) . . ? C22 C17 C18 119.8(4) . . ? C22 C17 S8 123.3(3) . . ? C18 C17 S8 116.9(3) . . ? C21 C20 C19 120.8(4) . . ? C21 C22 C17 118.9(4) . . ? C20 C21 C22 121.3(4) . . ? C24 C23 O5 107.4(5) . . ? O5 C26 C25 107.0(4) . . ? C26 C25 C24 101.6(4) . . ? C23 C24 C25 101.3(5) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.87 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.831 _refine_diff_density_min -0.417 _refine_diff_density_rms 0.086 # SQUEEZE RESULTS loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.250 0.028 0.000 186 18 ' ' 2 0.250 -0.097 0.500 186 18 ' ' 3 0.750 -0.105 0.000 186 18 ' ' 4 0.750 0.038 0.500 186 18 ' ' _platon_squeeze_details ; ; _database_code_depnum_ccdc_archive 'CCDC 926914'