# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_shelxl _database_code_depnum_ccdc_archive 'CCDC 907004' #TrackingRef 'web_deposit_cif_file_3_ChaeIlSeok_1350886122.SHELXL.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H27 N O5 S' _chemical_formula_weight 333.44 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' N N 0.0311 0.0180 '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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.5326(16) _cell_length_b 10.2411(18) _cell_length_c 11.634(2) _cell_angle_alpha 97.339(12) _cell_angle_beta 108.413(12) _cell_angle_gamma 106.459(12) _cell_volume 898.3(3) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.233 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 360 _exptl_absorpt_coefficient_mu 1.788 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.4135 _exptl_absorpt_correction_T_max 0.6635 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 1.54187 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9494 _diffrn_reflns_av_R_equivalents 0.0755 _diffrn_reflns_av_sigmaI/netI 0.0871 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 4.12 _diffrn_reflns_theta_max 68.25 _reflns_number_total 3195 _reflns_number_gt 2341 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^ > 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^)+(0.1515P)^2^+1.2447P] 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 3195 _refine_ls_number_parameters 247 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1161 _refine_ls_R_factor_gt 0.0950 _refine_ls_wR_factor_ref 0.2742 _refine_ls_wR_factor_gt 0.2562 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _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 S1 S 0.25793(14) 0.92142(11) 1.21049(10) 0.0340(4) Uani 1 1 d . . . O2 O 0.2630(4) 0.8166(3) 1.1155(3) 0.0394(8) Uani 1 1 d . . . O3 O 0.2176(5) 0.5018(4) 0.7813(4) 0.0561(11) Uani 1 1 d . . . O4 O 0.1352(5) 0.9884(4) 1.1512(4) 0.0517(10) Uani 1 1 d . . . O5 O 0.4282(4) 1.0158(4) 1.2930(3) 0.0539(10) Uani 1 1 d . . . O6 O 0.1692(7) 0.4394(5) 0.5818(4) 0.0859(17) Uani 1 1 d . . . N7 N 0.0289(5) 0.8169(4) 0.8686(4) 0.0300(9) Uani 1 1 d . . . H7 H 0.085(7) 0.823(6) 0.943(5) 0.046(16) Uiso 1 1 d . . . C8 C 0.3430(6) 0.3410(4) 0.7212(4) 0.0338(10) Uani 1 1 d . . . C9 C 0.1627(6) 0.8566(4) 0.8051(4) 0.0329(10) Uani 1 1 d . . . C10 C 0.2534(7) 0.7473(5) 0.8103(5) 0.0377(11) Uani 1 1 d . . . H10A H 0.321(6) 0.749(5) 0.896(5) 0.037(13) Uiso 1 1 d . . . H10B H 0.312(7) 0.758(5) 0.762(5) 0.045(15) Uiso 1 1 d . . . C11 C 0.2378(6) 0.4317(5) 0.6853(5) 0.0425(12) Uani 1 1 d . . . C12 C -0.1053(6) 0.6707(4) 0.8294(5) 0.0361(11) Uani 1 1 d . . . C13 C -0.2441(6) 0.6462(5) 0.7011(5) 0.0429(12) Uani 1 1 d . . . H13A H -0.2819 0.7279 0.6964 0.051 Uiso 1 1 calc R . . H13B H -0.3455 0.5628 0.6872 0.051 Uiso 1 1 calc R . . H13C H -0.1945 0.6320 0.6371 0.051 Uiso 1 1 calc R . . C14 C 0.0733(8) 0.8676(6) 0.6727(5) 0.0489(13) Uani 1 1 d . . . H14A H -0.0084 0.7749 0.6216 0.059 Uiso 1 1 calc R . . H14B H 0.1625 0.9026 0.6371 0.059 Uiso 1 1 calc R . . H14C H 0.0084 0.9324 0.6742 0.059 Uiso 1 1 calc R . . C15 C -0.0045(7) 0.5676(5) 0.8333(5) 0.0461(13) Uani 1 1 d . . . H15A H 0.059(6) 0.573(5) 0.929(5) 0.039(13) Uiso 1 1 d . . . H15B H -0.091(8) 0.472(7) 0.803(5) 0.062(17) Uiso 1 1 d . . . C16 C -0.1888(8) 0.6629(6) 0.9279(6) 0.0461(13) Uani 1 1 d . . . H16A H -0.244(6) 0.724(5) 0.918(4) 0.033(13) Uiso 1 1 d . . . H16B H -0.097(7) 0.687(5) 1.015(5) 0.039(13) Uiso 1 1 d . . . H16C H -0.267(8) 0.578(7) 0.908(6) 0.066(19) Uiso 1 1 d . . . C17 C 0.2919(7) 1.0008(5) 0.8831(6) 0.0444(13) Uani 1 1 d . . . H17A H 0.340(7) 0.990(6) 0.967(6) 0.053(16) Uiso 1 1 d . . . H17B H 0.395(8) 1.033(6) 0.853(6) 0.069(18) Uiso 1 1 d . . . H17C H 0.233(7) 1.076(6) 0.876(5) 0.049(14) Uiso 1 1 d . . . C18 C 0.1195(8) 0.5980(5) 0.7595(5) 0.0480(13) Uani 1 1 d . . . H18 H 0.052(8) 0.586(6) 0.666(6) 0.059(17) Uiso 1 1 d . . . C19 C 0.4229(7) 0.3455(5) 0.8404(5) 0.0466(13) Uani 1 1 d . . . H19A H 0.3352 0.3213 0.8791 0.056 Uiso 1 1 calc R . . H19B H 0.5071 0.4402 0.8833 0.056 Uiso 1 1 calc R . . H19C H 0.4855 0.2783 0.8468 0.056 Uiso 1 1 calc R . . C20 C 0.1620(7) 0.8262(5) 1.3000(5) 0.0443(12) Uani 1 1 d . . . H20 H 0.0421 0.7675 1.2607 0.053 Uiso 1 1 calc R . . C21 C 0.2420(9) 0.8295(6) 1.4163(5) 0.0604(16) Uani 1 1 d . . . H21A H 0.3620 0.8869 1.4589 0.072 Uiso 1 1 calc R . . H21B H 0.1806 0.7744 1.4587 0.072 Uiso 1 1 calc R . . C22 C 0.3557(9) 0.2482(7) 0.6167(6) 0.072(2) Uani 1 1 d . . . H22A H 0.4234 0.1888 0.6344 0.086 Uiso 1 1 calc R . . H22B H 0.2960 0.2487 0.5327 0.086 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 S1 0.0273(6) 0.0323(6) 0.0416(7) -0.0005(5) 0.0125(5) 0.0133(5) O2 0.0397(19) 0.0451(19) 0.0393(18) 0.0027(15) 0.0152(15) 0.0258(16) O3 0.070(3) 0.054(2) 0.054(2) 0.0063(18) 0.021(2) 0.043(2) O4 0.058(2) 0.049(2) 0.064(2) 0.0140(18) 0.025(2) 0.0384(19) O5 0.037(2) 0.054(2) 0.053(2) -0.0087(18) 0.0138(17) 0.0016(17) O6 0.112(4) 0.106(4) 0.046(2) -0.006(2) 0.002(3) 0.089(3) N7 0.0247(19) 0.0275(19) 0.034(2) -0.0023(16) 0.0112(17) 0.0071(15) C8 0.027(2) 0.026(2) 0.043(3) 0.0014(19) 0.009(2) 0.0089(18) C9 0.031(2) 0.029(2) 0.044(3) 0.0059(19) 0.020(2) 0.0136(19) C10 0.036(3) 0.042(3) 0.042(3) 0.006(2) 0.016(2) 0.022(2) C11 0.035(3) 0.041(3) 0.048(3) 0.000(2) 0.013(2) 0.015(2) C12 0.031(2) 0.025(2) 0.047(3) -0.0025(19) 0.012(2) 0.0083(19) C13 0.033(3) 0.034(2) 0.048(3) -0.006(2) 0.006(2) 0.009(2) C14 0.058(3) 0.062(3) 0.047(3) 0.016(3) 0.028(3) 0.039(3) C15 0.051(3) 0.029(3) 0.054(3) 0.000(2) 0.011(3) 0.020(2) C16 0.039(3) 0.036(3) 0.056(4) 0.003(2) 0.021(3) 0.002(3) C17 0.037(3) 0.035(3) 0.071(4) 0.012(3) 0.030(3) 0.014(2) C18 0.058(3) 0.042(3) 0.051(3) 0.005(2) 0.020(3) 0.032(3) C19 0.038(3) 0.033(3) 0.067(4) 0.009(2) 0.021(3) 0.008(2) C20 0.040(3) 0.040(3) 0.049(3) -0.003(2) 0.019(2) 0.012(2) C21 0.067(4) 0.064(4) 0.048(3) 0.002(3) 0.029(3) 0.016(3) C22 0.087(5) 0.081(4) 0.061(4) 0.001(3) 0.018(4) 0.066(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O5 1.433(4) . ? S1 O4 1.454(3) . ? S1 O2 1.459(3) . ? S1 C20 1.747(5) . ? O3 C11 1.335(6) . ? O3 C18 1.460(6) . ? O6 C11 1.185(6) . ? N7 C12 1.512(6) . ? N7 C9 1.537(6) . ? N7 H7 0.83(6) . ? C8 C19 1.326(7) . ? C8 C11 1.475(6) . ? C8 C22 1.496(7) . ? C9 C14 1.522(7) . ? C9 C17 1.524(7) . ? C9 C10 1.527(6) . ? C10 C18 1.532(7) . ? C10 H10A 0.98(5) . ? C10 H10B 0.86(5) . ? C12 C13 1.521(7) . ? C12 C16 1.528(7) . ? C12 C15 1.535(6) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C18 1.552(8) . ? C15 H15A 1.06(5) . ? C15 H15B 0.99(6) . ? C16 H16A 0.88(5) . ? C16 H16B 1.02(5) . ? C16 H16C 0.88(7) . ? C17 H17A 0.96(6) . ? C17 H17B 1.03(6) . ? C17 H17C 1.03(5) . ? C18 H18 1.03(6) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C21 1.299(8) . ? C20 H20 0.9500 . ? C21 H21A 0.9500 . ? C21 H21B 0.9500 . ? C22 H22A 0.9500 . ? C22 H22B 0.9500 . ? 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 O5 S1 O4 115.0(2) . . ? O5 S1 O2 113.8(2) . . ? O4 S1 O2 109.3(2) . . ? O5 S1 C20 107.3(2) . . ? O4 S1 C20 105.3(2) . . ? O2 S1 C20 105.3(2) . . ? C11 O3 C18 119.2(4) . . ? C12 N7 C9 120.6(3) . . ? C12 N7 H7 102(4) . . ? C9 N7 H7 108(4) . . ? C19 C8 C11 120.6(4) . . ? C19 C8 C22 123.1(4) . . ? C11 C8 C22 116.3(4) . . ? C14 C9 C17 109.0(4) . . ? C14 C9 C10 113.0(4) . . ? C17 C9 C10 111.3(4) . . ? C14 C9 N7 110.8(4) . . ? C17 C9 N7 104.9(4) . . ? C10 C9 N7 107.6(4) . . ? C9 C10 C18 111.5(4) . . ? C9 C10 H10A 111(3) . . ? C18 C10 H10A 104(3) . . ? C9 C10 H10B 108(3) . . ? C18 C10 H10B 106(4) . . ? H10A C10 H10B 116(5) . . ? O6 C11 O3 121.4(5) . . ? O6 C11 C8 125.1(5) . . ? O3 C11 C8 113.4(4) . . ? N7 C12 C13 110.9(4) . . ? N7 C12 C16 105.3(4) . . ? C13 C12 C16 110.4(4) . . ? N7 C12 C15 107.2(4) . . ? C13 C12 C15 112.4(4) . . ? C16 C12 C15 110.4(5) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C9 C14 H14A 109.5 . . ? C9 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C9 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C12 C15 C18 111.8(4) . . ? C12 C15 H15A 106(3) . . ? C18 C15 H15A 115(3) . . ? C12 C15 H15B 108(3) . . ? C18 C15 H15B 113(3) . . ? H15A C15 H15B 102(4) . . ? C12 C16 H16A 104(3) . . ? C12 C16 H16B 112(3) . . ? H16A C16 H16B 111(4) . . ? C12 C16 H16C 107(4) . . ? H16A C16 H16C 109(5) . . ? H16B C16 H16C 113(5) . . ? C9 C17 H17A 106(3) . . ? C9 C17 H17B 111(3) . . ? H17A C17 H17B 107(5) . . ? C9 C17 H17C 112(3) . . ? H17A C17 H17C 114(5) . . ? H17B C17 H17C 106(4) . . ? O3 C18 C10 107.4(4) . . ? O3 C18 C15 105.5(4) . . ? C10 C18 C15 111.6(4) . . ? O3 C18 H18 112(3) . . ? C10 C18 H18 108(3) . . ? C15 C18 H18 113(3) . . ? C8 C19 H19A 109.5 . . ? C8 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C8 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 C20 S1 125.0(5) . . ? C21 C20 H20 117.5 . . ? S1 C20 H20 117.5 . . ? C20 C21 H21A 120.0 . . ? C20 C21 H21B 120.0 . . ? H21A C21 H21B 120.0 . . ? C8 C22 H22A 120.0 . . ? C8 C22 H22B 120.0 . . ? H22A C22 H22B 120.0 . . ? 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 C12 N7 C9 C14 71.7(5) . . . . ? C12 N7 C9 C17 -170.7(4) . . . . ? C12 N7 C9 C10 -52.2(5) . . . . ? C14 C9 C10 C18 -70.7(6) . . . . ? C17 C9 C10 C18 166.3(5) . . . . ? N7 C9 C10 C18 51.9(5) . . . . ? C18 O3 C11 O6 -4.6(8) . . . . ? C18 O3 C11 C8 178.6(4) . . . . ? C19 C8 C11 O6 176.2(6) . . . . ? C22 C8 C11 O6 -2.7(8) . . . . ? C19 C8 C11 O3 -7.1(7) . . . . ? C22 C8 C11 O3 174.0(5) . . . . ? C9 N7 C12 C13 -71.3(5) . . . . ? C9 N7 C12 C16 169.3(4) . . . . ? C9 N7 C12 C15 51.8(6) . . . . ? N7 C12 C15 C18 -51.5(6) . . . . ? C13 C12 C15 C18 70.6(5) . . . . ? C16 C12 C15 C18 -165.7(4) . . . . ? C11 O3 C18 C10 -105.8(5) . . . . ? C11 O3 C18 C15 135.1(5) . . . . ? C9 C10 C18 O3 -173.7(4) . . . . ? C9 C10 C18 C15 -58.6(6) . . . . ? C12 C15 C18 O3 174.7(4) . . . . ? C12 C15 C18 C10 58.5(6) . . . . ? O5 S1 C20 C21 -8.1(6) . . . . ? O4 S1 C20 C21 -131.1(5) . . . . ? O2 S1 C20 C21 113.5(5) . . . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 68.25 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.987 _refine_diff_density_min -1.146 _refine_diff_density_rms 0.098