# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 #TrackingRef '- archive.cif' #------------------ AUDIT DETAILS -------------------------------------------# _audit_creation_date 2010-06-07 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic _audit_update_record ? #------------------ AUTHOR DETAILS -------------------------------------------# # Name and address of author for correspondence _publ_contact_author_name 'Farrugia, Louis J.' # Name of author for correspondence _publ_contact_author_address ; Department of Chemistry University of Glasgow Glasgow G12 8QQ, UK ; # Address of author for correspondence _publ_contact_author_email louis@chem.gla.ac.uk _publ_contact_author_fax 44(0141)3304888 _publ_contact_author_phone 44(0141)3305137 # Insert blank lines between references _publ_section_references ; Blessing, R. H. (1995) Acta Cryst., A51, 33-38. Blessing, R. H. (1987) Cryst. Rev. 1, 3-58. Blessing, R. H. (1989) J. Appl. Cryst. 22, 396-397. APEX, APEX2, SMART, SAINT, SAINT-Plus: Bruker (2007). Program name(s). Bruker AXS Inc., Madison, Wisconsin, USA. [Older versions (pre-1997) should refer to Siemens Analytical X-ray Instruments Inc. instead of Bruker AXS.] ORTEP-3: Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. PLATON: Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13. SADABS, TWINABS: Bruker (2001). Program name. Bruker AXS Inc., Madison, Wisconsin, USA. or Sheldrick, G. M. (1996). Program name. University of G ttingen, Germany. SHELX Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122. SIR92: Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. WinGX: Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838. ; _publ_requested_category FO _publ_author_name 'Louis J. Farrugia' #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# data_compound_1a _database_code_depnum_ccdc_archive 'CCDC 891354' #TrackingRef '- archive.cif' _audit_creation_date 2010-06-07T14:18:31-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C30 H22 O8 S4, 2(C4 H8 O2 S)' _chemical_formula_sum 'C38 H38 O12 S6' _chemical_formula_weight 879.04 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'I 2/a' _symmetry_space_group_name_Hall '-I 2ya' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z' '-x+1/2, -y+1/2, -z+1/2' 'x, -y+1/2, z+1/2' _cell_length_a 18.3523(13) _cell_length_b 11.5228(8) _cell_length_c 18.6286(14) _cell_angle_alpha 90 _cell_angle_beta 90.916(6) _cell_angle_gamma 90 _cell_volume 3938.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9895 _cell_measurement_theta_min 2.2197 _cell_measurement_theta_max 34.8173 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.482 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1832 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.411 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2008/1 - Bruker AXS area detector scaling and absorption correction ; _exptl_absorpt_correction_T_min 0.663 _exptl_absorpt_correction_T_max 0.747 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'sealed x-ray tube' _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'APEX-II CCD' _diffrn_orient_matrix_type 'x-axis to radiation source' _diffrn_orient_matrix_ub_11 -0.468577E-1 _diffrn_orient_matrix_ub_12 -0.248359E-1 _diffrn_orient_matrix_ub_13 -0.676418E-1 _diffrn_orient_matrix_ub_21 0.142704E-1 _diffrn_orient_matrix_ub_22 -0.831481E-1 _diffrn_orient_matrix_ub_23 0.198537E-1 _diffrn_orient_matrix_ub_31 -0.21978E-1 _diffrn_orient_matrix_ub_32 -0.103759E-2 _diffrn_orient_matrix_ub_33 0.280888E-1 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Bruker APEX-II' _diffrn_measurement_method '\f or \w oscillation scans' _diffrn_reflns_av_R_equivalents 0.035 _diffrn_reflns_av_unetI/netI 0.0338 _diffrn_reflns_number 60930 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 34.89 _diffrn_reflns_theta_full 34.89 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 8583 _reflns_number_gt 7301 _reflns_threshold_expression >2\s(I) _diffrn_reflns_reduction_process ; Scaled and merged with Sortav R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 After data reduction, the structure was transformed from the input space group of C2/c (having a beta angle of ~134 deg) to the non-standard I2/a cell with a beta angle closer to 90 deg. This was done to remove many high correlations in the refinement. The data given for _diffrn_reflns_limit_h_min etc are for the original C2/c cell ; #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker APEX2 software' _computing_cell_refinement 'SAINT V7.68A integration software' _computing_data_reduction 'SORTAV (Blessing, 1995)' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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 high value for the ratio of maximum / minimum residual density is due the high quality and the relatively high resolution of the data. These preponderance of peaks as opposed to troughs is because these are bonding density peaks, which are a necessary result of the spherical atom approximation for the atomic scattering factors. The strongest peaks lie at the centre of the covalent bonds. ; _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^)+(0.0584P)^2^+1.8791P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 8583 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0443 _refine_ls_R_factor_gt 0.0366 _refine_ls_wR_factor_ref 0.1056 _refine_ls_wR_factor_gt 0.1021 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.857 _refine_diff_density_min -0.284 _refine_diff_density_rms 0.092 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.827494(12) 1.06162(2) 0.446493(12) 0.01374(5) Uani 1 1 d . . . S2 S 0.835363(12) 0.59967(2) 0.455889(12) 0.01366(5) Uani 1 1 d . . . O11 O 0.77411(4) 1.14569(7) 0.42371(4) 0.01724(13) Uani 1 1 d . . . O12 O 0.87834(4) 1.01916(7) 0.39431(4) 0.02018(14) Uani 1 1 d . . . O21 O 0.90528(4) 0.64676(7) 0.43727(5) 0.02013(14) Uani 1 1 d . . . O22 O 0.83178(4) 0.51690(7) 0.51362(4) 0.01732(13) Uani 1 1 d . . . C1 C 0.78137(5) 0.93514(8) 0.47906(5) 0.01269(14) Uani 1 1 d . . . C2 C 0.81220(5) 0.82967(8) 0.45935(5) 0.01316(14) Uani 1 1 d . . . H2 H 0.855 0.8297 0.4313 0.016 Uiso 1 1 calc R . . C3 C 0.78183(5) 0.72414(8) 0.47982(5) 0.01205(14) Uani 1 1 d . . . C111 C 0.87727(5) 1.11581(8) 0.52059(5) 0.01533(15) Uani 1 1 d . . . C112 C 0.91865(7) 1.04064(10) 0.56271(7) 0.0269(2) Uani 1 1 d . . . H112 H 0.9184 0.9596 0.5533 0.032 Uiso 1 1 calc R . . C113 C 0.96046(7) 1.08587(12) 0.61894(8) 0.0302(3) Uani 1 1 d . . . H113 H 0.9882 1.0354 0.649 0.036 Uiso 1 1 calc R . . C114 C 0.96178(6) 1.20441(11) 0.63121(7) 0.0248(2) Uani 1 1 d . . . H114 H 0.9912 1.2352 0.6691 0.03 Uiso 1 1 calc R . . C115 C 0.92028(7) 1.27845(10) 0.58823(7) 0.0253(2) Uani 1 1 d . . . H115 H 0.9216 1.3598 0.5966 0.03 Uiso 1 1 calc R . . C116 C 0.87682(6) 1.23400(9) 0.53303(6) 0.02059(18) Uani 1 1 d . . . H116 H 0.8473 1.284 0.5043 0.025 Uiso 1 1 calc R . . C211 C 0.79646(5) 0.53921(9) 0.37751(5) 0.01578(16) Uani 1 1 d . . . C212 C 0.76640(6) 0.42858(9) 0.37998(5) 0.01871(17) Uani 1 1 d . . . H212 H 0.7632 0.3882 0.4243 0.022 Uiso 1 1 calc R . . C213 C 0.74118(7) 0.37794(10) 0.31667(6) 0.0242(2) Uani 1 1 d . . . H213 H 0.7209 0.3021 0.3173 0.029 Uiso 1 1 calc R . . C214 C 0.74565(8) 0.43837(12) 0.25232(6) 0.0284(2) Uani 1 1 d . . . H214 H 0.728 0.4037 0.2092 0.034 Uiso 1 1 calc R . . C215 C 0.77573(8) 0.54906(12) 0.25039(6) 0.0301(3) Uani 1 1 d . . . H215 H 0.7785 0.5895 0.2061 0.036 Uiso 1 1 calc R . . C216 C 0.80177(7) 0.60062(10) 0.31341(6) 0.0231(2) Uani 1 1 d . . . H216 H 0.8227 0.676 0.3127 0.028 Uiso 1 1 calc R . . S3 S -0.079858(14) 0.73835(2) 0.662775(13) 0.01788(6) Uani 1 1 d . . . O31 O -0.14866(5) 0.76585(9) 0.62825(5) 0.02625(17) Uani 1 1 d . . . O32 O -0.05688(5) 0.80922(9) 0.72274(5) 0.02820(18) Uani 1 1 d . . . C31 C -0.00800(7) 0.73429(11) 0.59833(7) 0.0254(2) Uani 1 1 d . . . H31A H -0.0269 0.7549 0.5499 0.03 Uiso 1 1 calc R . . H31B H 0.0313 0.7893 0.6119 0.03 Uiso 1 1 calc R . . C32 C 0.02043(8) 0.60929(12) 0.59943(8) 0.0321(3) Uani 1 1 d . . . H32A H -0.0041 0.5632 0.5612 0.038 Uiso 1 1 calc R . . H32B H 0.0735 0.6084 0.5909 0.038 Uiso 1 1 calc R . . C33 C 0.00441(7) 0.55741(11) 0.67319(7) 0.0283(2) Uani 1 1 d . . . H33A H 0.0107 0.4721 0.6726 0.034 Uiso 1 1 calc R . . H33B H 0.0374 0.5906 0.7104 0.034 Uiso 1 1 calc R . . C34 C -0.07466(7) 0.58941(11) 0.68791(7) 0.0273(2) Uani 1 1 d . . . H34A H -0.086 0.579 0.7393 0.033 Uiso 1 1 calc R . . H34B H -0.1087 0.5417 0.6586 0.033 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 0.01650(10) 0.01061(10) 0.01413(9) 0.00126(7) 0.00045(7) -0.00110(7) S2 0.01453(10) 0.01041(10) 0.01603(10) -0.00110(7) -0.00024(7) 0.00128(7) O11 0.0212(3) 0.0135(3) 0.0170(3) 0.0034(2) -0.0028(2) 0.0011(2) O12 0.0235(3) 0.0172(3) 0.0201(3) 0.0007(3) 0.0076(3) -0.0012(3) O21 0.0144(3) 0.0165(3) 0.0296(4) -0.0024(3) 0.0028(3) 0.0003(2) O22 0.0221(3) 0.0130(3) 0.0168(3) 0.0016(2) -0.0031(2) 0.0034(2) C1 0.0154(3) 0.0101(3) 0.0125(3) 0.0003(3) -0.0007(3) -0.0002(3) C2 0.0148(3) 0.0104(3) 0.0143(3) -0.0002(3) 0.0001(3) -0.0002(3) C3 0.0134(3) 0.0101(3) 0.0125(3) -0.0007(3) -0.0012(3) 0.0004(3) C111 0.0147(3) 0.0123(4) 0.0188(4) 0.0002(3) -0.0021(3) -0.0009(3) C112 0.0325(6) 0.0151(5) 0.0327(6) -0.0016(4) -0.0152(4) 0.0038(4) C113 0.0315(6) 0.0234(6) 0.0352(6) -0.0016(4) -0.0172(5) 0.0039(4) C114 0.0216(5) 0.0238(5) 0.0286(5) -0.0038(4) -0.0070(4) -0.0031(4) C115 0.0288(5) 0.0164(5) 0.0303(5) -0.0039(4) -0.0071(4) -0.0038(4) C116 0.0237(4) 0.0129(4) 0.0250(5) -0.0005(3) -0.0053(4) -0.0004(3) C211 0.0203(4) 0.0129(4) 0.0142(3) -0.0014(3) 0.0015(3) 0.0008(3) C212 0.0264(5) 0.0131(4) 0.0166(4) -0.0018(3) -0.0010(3) 0.0001(3) C213 0.0348(6) 0.0183(5) 0.0193(4) -0.0048(3) -0.0028(4) -0.0019(4) C214 0.0426(7) 0.0265(6) 0.0162(4) -0.0045(4) -0.0028(4) -0.0006(5) C215 0.0472(7) 0.0291(6) 0.0140(4) 0.0011(4) 0.0013(4) -0.0039(5) C216 0.0330(5) 0.0199(5) 0.0166(4) 0.0017(3) 0.0029(4) -0.0034(4) S3 0.01874(11) 0.01682(11) 0.01798(11) -0.00267(8) -0.00290(8) 0.00294(8) O31 0.0224(4) 0.0303(5) 0.0258(4) -0.0027(3) -0.0077(3) 0.0058(3) O32 0.0309(4) 0.0274(4) 0.0259(4) -0.0108(3) -0.0095(3) 0.0064(3) C31 0.0259(5) 0.0212(5) 0.0293(5) 0.0009(4) 0.0052(4) 0.0046(4) C32 0.0350(6) 0.0266(6) 0.0348(6) 0.0007(5) 0.0056(5) 0.0127(5) C33 0.0310(6) 0.0213(5) 0.0325(6) 0.0017(4) -0.0043(4) 0.0077(4) C34 0.0304(6) 0.0205(5) 0.0311(6) 0.0033(4) 0.0014(4) 0.0013(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 S1 O11 1.4370(8) . ? S1 O12 1.4436(8) . ? S1 C111 1.7577(10) . ? S1 C1 1.7959(9) . ? S2 O22 1.4397(8) . ? S2 O21 1.4407(8) . ? S2 C211 1.7590(10) . ? S2 C3 1.7986(9) . ? C1 C2 1.3923(13) . ? C1 C1 1.4010(18) 2_656 ? C2 C3 1.3934(13) . ? C2 H2 0.95 . ? C3 C3 1.3995(18) 2_656 ? C111 C116 1.3815(15) . ? C111 C112 1.3867(15) . ? C112 C113 1.3900(16) . ? C112 H112 0.95 . ? C113 C114 1.3850(18) . ? C113 H113 0.95 . ? C114 C115 1.3891(17) . ? C114 H114 0.95 . ? C115 C116 1.3892(15) . ? C115 H115 0.95 . ? C116 H116 0.95 . ? C211 C212 1.3900(14) . ? C211 C216 1.3927(14) . ? C212 C213 1.3886(15) . ? C212 H212 0.95 . ? C213 C214 1.3898(17) . ? C213 H213 0.95 . ? C214 C215 1.3906(19) . ? C214 H214 0.95 . ? C215 C216 1.3934(17) . ? C215 H215 0.95 . ? C216 H216 0.95 . ? S3 O32 1.4414(9) . ? S3 O31 1.4431(9) . ? S3 C34 1.7811(13) . ? S3 C31 1.7981(12) . ? C31 C32 1.5320(18) . ? C31 H31A 0.99 . ? C31 H31B 0.99 . ? C32 C33 1.531(2) . ? C32 H32A 0.99 . ? C32 H32B 0.99 . ? C33 C34 1.5263(18) . ? C33 H33A 0.99 . ? C33 H33B 0.99 . ? C34 H34A 0.99 . ? C34 H34B 0.99 . ? 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 O11 S1 O12 118.33(5) . . ? O11 S1 C111 109.62(5) . . ? O12 S1 C111 108.41(5) . . ? O11 S1 C1 108.90(4) . . ? O12 S1 C1 105.41(5) . . ? C111 S1 C1 105.36(4) . . ? O22 S2 O21 118.74(5) . . ? O22 S2 C211 109.56(5) . . ? O21 S2 C211 107.50(5) . . ? O22 S2 C3 108.15(4) . . ? O21 S2 C3 104.57(4) . . ? C211 S2 C3 107.79(4) . . ? C2 C1 C1 119.21(5) . 2_656 ? C2 C1 S1 115.05(7) . . ? C1 C1 S1 125.74(3) 2_656 . ? C1 C2 C3 121.57(8) . . ? C1 C2 H2 119.2 . . ? C3 C2 H2 119.2 . . ? C2 C3 C3 119.22(5) . 2_656 ? C2 C3 S2 113.93(7) . . ? C3 C3 S2 126.67(3) 2_656 . ? C116 C111 C112 121.70(9) . . ? C116 C111 S1 118.52(8) . . ? C112 C111 S1 119.70(8) . . ? C111 C112 C113 118.88(11) . . ? C111 C112 H112 120.6 . . ? C113 C112 H112 120.6 . . ? C114 C113 C112 120.14(11) . . ? C114 C113 H113 119.9 . . ? C112 C113 H113 119.9 . . ? C113 C114 C115 120.18(10) . . ? C113 C114 H114 119.9 . . ? C115 C114 H114 119.9 . . ? C114 C115 C116 120.21(11) . . ? C114 C115 H115 119.9 . . ? C116 C115 H115 119.9 . . ? C111 C116 C115 118.86(10) . . ? C111 C116 H116 120.6 . . ? C115 C116 H116 120.6 . . ? C212 C211 C216 121.85(9) . . ? C212 C211 S2 119.45(7) . . ? C216 C211 S2 118.52(8) . . ? C213 C212 C211 118.96(10) . . ? C213 C212 H212 120.5 . . ? C211 C212 H212 120.5 . . ? C212 C213 C214 119.90(11) . . ? C212 C213 H213 120 . . ? C214 C213 H213 120 . . ? C213 C214 C215 120.72(11) . . ? C213 C214 H214 119.6 . . ? C215 C214 H214 119.6 . . ? C214 C215 C216 120.01(11) . . ? C214 C215 H215 120 . . ? C216 C215 H215 120 . . ? C211 C216 C215 118.55(11) . . ? C211 C216 H216 120.7 . . ? C215 C216 H216 120.7 . . ? O32 S3 O31 117.65(5) . . ? O32 S3 C34 109.17(6) . . ? O31 S3 C34 111.81(6) . . ? O32 S3 C31 108.88(6) . . ? O31 S3 C31 110.73(6) . . ? C34 S3 C31 96.53(6) . . ? C32 C31 S3 105.59(9) . . ? C32 C31 H31A 110.6 . . ? S3 C31 H31A 110.6 . . ? C32 C31 H31B 110.6 . . ? S3 C31 H31B 110.6 . . ? H31A C31 H31B 108.8 . . ? C33 C32 C31 107.99(10) . . ? C33 C32 H32A 110.1 . . ? C31 C32 H32A 110.1 . . ? C33 C32 H32B 110.1 . . ? C31 C32 H32B 110.1 . . ? H32A C32 H32B 108.4 . . ? C34 C33 C32 105.29(10) . . ? C34 C33 H33A 110.7 . . ? C32 C33 H33A 110.7 . . ? C34 C33 H33B 110.7 . . ? C32 C33 H33B 110.7 . . ? H33A C33 H33B 108.8 . . ? C33 C34 S3 103.45(9) . . ? C33 C34 H34A 111.1 . . ? S3 C34 H34A 111.1 . . ? C33 C34 H34B 111.1 . . ? S3 C34 H34B 111.1 . . ? H34A C34 H34B 109 . . ? 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 O11 S1 C1 C2 139.46(7) . . . . ? O12 S1 C1 C2 11.53(8) . . . . ? C111 S1 C1 C2 -103.01(7) . . . . ? O11 S1 C1 C1 -40.11(12) . . . 2_656 ? O12 S1 C1 C1 -168.04(11) . . . 2_656 ? C111 S1 C1 C1 77.42(12) . . . 2_656 ? C1 C1 C2 C3 0.50(16) 2_656 . . . ? S1 C1 C2 C3 -179.10(7) . . . . ? C1 C2 C3 C3 1.03(15) . . . 2_656 ? C1 C2 C3 S2 -174.31(7) . . . . ? O22 S2 C3 C2 141.47(7) . . . . ? O21 S2 C3 C2 14.03(8) . . . . ? C211 S2 C3 C2 -100.16(7) . . . . ? O22 S2 C3 C3 -33.46(12) . . . 2_656 ? O21 S2 C3 C3 -160.90(11) . . . 2_656 ? C211 S2 C3 C3 84.92(11) . . . 2_656 ? O11 S1 C111 C116 -19.28(10) . . . . ? O12 S1 C111 C116 111.24(9) . . . . ? C1 S1 C111 C116 -136.32(9) . . . . ? O11 S1 C111 C112 163.93(9) . . . . ? O12 S1 C111 C112 -65.55(10) . . . . ? C1 S1 C111 C112 46.89(10) . . . . ? C116 C111 C112 C113 0.19(19) . . . . ? S1 C111 C112 C113 176.88(11) . . . . ? C111 C112 C113 C114 -1.5(2) . . . . ? C112 C113 C114 C115 1.2(2) . . . . ? C113 C114 C115 C116 0.5(2) . . . . ? C112 C111 C116 C115 1.45(17) . . . . ? S1 C111 C116 C115 -175.28(9) . . . . ? C114 C115 C116 C111 -1.76(18) . . . . ? O22 S2 C211 C212 2.17(10) . . . . ? O21 S2 C211 C212 132.49(8) . . . . ? C3 S2 C211 C212 -115.30(8) . . . . ? O22 S2 C211 C216 -173.00(8) . . . . ? O21 S2 C211 C216 -42.68(10) . . . . ? C3 S2 C211 C216 69.54(9) . . . . ? C216 C211 C212 C213 0.16(16) . . . . ? S2 C211 C212 C213 -174.84(9) . . . . ? C211 C212 C213 C214 -0.58(18) . . . . ? C212 C213 C214 C215 0.5(2) . . . . ? C213 C214 C215 C216 0.0(2) . . . . ? C212 C211 C216 C215 0.31(17) . . . . ? S2 C211 C216 C215 175.36(10) . . . . ? C214 C215 C216 C211 -0.4(2) . . . . ? O32 S3 C31 C32 111.90(9) . . . . ? O31 S3 C31 C32 -117.27(9) . . . . ? C34 S3 C31 C32 -0.96(10) . . . . ? S3 C31 C32 C33 -25.71(13) . . . . ? C31 C32 C33 C34 46.56(14) . . . . ? C32 C33 C34 S3 -45.01(12) . . . . ? O32 S3 C34 C33 -85.79(9) . . . . ? O31 S3 C34 C33 142.27(8) . . . . ? C31 S3 C34 C33 26.83(10) . . . . ? #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# data_compound_1b _database_code_depnum_ccdc_archive 'CCDC 891355' #TrackingRef '- archive.cif' _audit_creation_date 2012-06-29T11:11:40-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4.2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C30 H22 O8 S4, 2(C7 H12 O)' _chemical_formula_sum 'C44 H46 O10 S4' _chemical_formula_weight 863.05 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'I 2/c' _symmetry_space_group_name_Hall '-I 2yc' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z+1/2' '-x+1/2, y+1/2, -z+1' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 19.1198(6) _cell_length_b 11.6030(4) _cell_length_c 19.1943(5) _cell_angle_alpha 90 _cell_angle_beta 102.023(2) _cell_angle_gamma 90 _cell_volume 4164.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9884 _cell_measurement_theta_min 2.1697 _cell_measurement_theta_max 31.2255 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.376 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1816 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.287 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2008/1 - Bruker AXS area detector scaling and absorption correction ; _exptl_absorpt_correction_T_min 0.682 _exptl_absorpt_correction_T_max 0.746 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'sealed x-ray tube' _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'APEX-II CCD' _diffrn_orient_matrix_type 'x-axis to radiation source' _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Bruker APEX-II' _diffrn_measurement_method '\f or \w oscillation scans' _diffrn_reflns_av_R_equivalents 0.0824 _diffrn_reflns_av_unetI/netI 0.057 _diffrn_reflns_number 71078 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 31.96 _diffrn_reflns_theta_full 31.96 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 7196 _reflns_number_gt 5660 _reflns_threshold_expression >2\s(I) _diffrn_reflns_reduction_process ; Scaled and merged with Sortav R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 Data were transformed from standard C2/c setting to I2/c as the beta angle in the standard setting was close to 130 deg. Many high correlations were observed in refinement with C2/c, which were absent in I2/c. ; #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker APEX2 software' _computing_cell_refinement 'SAINT V7.68A integration software' _computing_data_reduction 'SORTAV (Blessing, 1995)' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.0512P)^2^+1.1685P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 7196 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.057 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.1039 _refine_ls_wR_factor_gt 0.0975 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.592 _refine_diff_density_min -0.41 _refine_diff_density_rms 0.074 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.554879(16) 0.58027(2) 0.837922(15) 0.01302(7) Uani 1 1 d . . . S2 S 0.561464(15) 1.03964(2) 0.831932(14) 0.01201(7) Uani 1 1 d . . . O11 O 0.50130(5) 0.49156(7) 0.82528(5) 0.01732(18) Uani 1 1 d . . . O12 O 0.57771(5) 0.62527(8) 0.90901(5) 0.01964(19) Uani 1 1 d . . . O21 O 0.61568(5) 0.99552(8) 0.88956(5) 0.01756(18) Uani 1 1 d . . . O22 O 0.58235(5) 1.11851(7) 0.78204(5) 0.01626(17) Uani 1 1 d . . . C1 C 0.52255(6) 0.70410(9) 0.78381(6) 0.0121(2) Uani 1 1 d . . . C2 C 0.54481(6) 0.80925(9) 0.81649(6) 0.0127(2) Uani 1 1 d . . . H2 H 0.5756 0.8093 0.8623 0.015 Uiso 1 1 calc R . . C3 C 0.52294(6) 0.91400(9) 0.78355(6) 0.0117(2) Uani 1 1 d . . . C111 C 0.63179(7) 0.53235(10) 0.80921(6) 0.0149(2) Uani 1 1 d . . . C112 C 0.69274(7) 0.60184(12) 0.82131(7) 0.0215(3) Uani 1 1 d . . . H112 H 0.6918 0.6764 0.8416 0.026 Uiso 1 1 calc R . . C113 C 0.75485(8) 0.56044(13) 0.80333(8) 0.0262(3) Uani 1 1 d . . . H113 H 0.7966 0.607 0.8109 0.031 Uiso 1 1 calc R . . C114 C 0.75582(7) 0.45056(13) 0.77421(8) 0.0244(3) Uani 1 1 d . . . H114 H 0.7985 0.4221 0.7624 0.029 Uiso 1 1 calc R . . C115 C 0.69467(7) 0.38247(12) 0.76230(7) 0.0224(3) Uani 1 1 d . . . H115 H 0.6957 0.3078 0.7423 0.027 Uiso 1 1 calc R . . C116 C 0.63192(7) 0.42296(11) 0.77951(7) 0.0175(2) Uani 1 1 d . . . H116 H 0.59 0.3768 0.7711 0.021 Uiso 1 1 calc R . . C211 C 0.49413(6) 1.10244(10) 0.86956(6) 0.0128(2) Uani 1 1 d . . . C212 C 0.48449(7) 1.22093(11) 0.86334(7) 0.0183(2) Uani 1 1 d . . . H212 H 0.5089 1.2648 0.8341 0.022 Uiso 1 1 calc R . . C213 C 0.43854(8) 1.27400(11) 0.90070(8) 0.0224(3) Uani 1 1 d . . . H213 H 0.4319 1.3551 0.8977 0.027 Uiso 1 1 calc R . . C214 C 0.40217(8) 1.20862(12) 0.94245(7) 0.0218(3) Uani 1 1 d . . . H214 H 0.3713 1.2455 0.9684 0.026 Uiso 1 1 calc R . . C215 C 0.41067(8) 1.08950(11) 0.94649(7) 0.0217(3) Uani 1 1 d . . . H215 H 0.3846 1.0451 0.974 0.026 Uiso 1 1 calc R . . C216 C 0.45738(7) 1.03542(11) 0.91020(7) 0.0181(2) Uani 1 1 d . . . H216 H 0.464 0.9543 0.9131 0.022 Uiso 1 1 calc R . . O31 O 0.89480(7) 0.74526(9) 0.86313(6) 0.0312(2) Uani 1 1 d . . . C31 C 0.87899(7) 0.79740(11) 0.91286(7) 0.0202(2) Uani 1 1 d . . . C32 C 0.86748(10) 0.73021(12) 0.97728(8) 0.0281(3) Uani 1 1 d . . . H32A H 0.9118 0.6863 0.996 0.034 Uiso 1 1 calc R . . H32B H 0.8292 0.6731 0.9605 0.034 Uiso 1 1 calc R . . C33 C 0.84794(9) 0.79587(13) 1.03945(8) 0.0283(3) Uani 1 1 d . . . H33A H 0.8858 0.8534 1.0567 0.034 Uiso 1 1 calc R . . H33B H 0.8475 0.7409 1.0788 0.034 Uiso 1 1 calc R . . C34 C 0.77557(8) 0.85830(15) 1.02233(8) 0.0292(3) Uani 1 1 d . . . H34A H 0.7404 0.8079 0.9915 0.035 Uiso 1 1 calc R . . H34B H 0.7589 0.8703 1.0673 0.035 Uiso 1 1 calc R . . C35 C 0.77689(7) 0.97415(13) 0.98551(7) 0.0234(3) Uani 1 1 d . . . H35A H 0.8125 1.0242 1.0162 0.028 Uiso 1 1 calc R . . H35B H 0.7295 1.011 0.9811 0.028 Uiso 1 1 calc R . . C36 C 0.79483(8) 0.96840(13) 0.91188(8) 0.0250(3) Uani 1 1 d . . . H36A H 0.7882 1.0461 0.8902 0.03 Uiso 1 1 calc R . . H36B H 0.7602 0.9162 0.8817 0.03 Uiso 1 1 calc R . . C37 C 0.87075(8) 0.92684(12) 0.91053(8) 0.0248(3) Uani 1 1 d . . . H37A H 0.8843 0.9561 0.8667 0.03 Uiso 1 1 calc R . . H37B H 0.9044 0.9605 0.9518 0.03 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 0.01572(14) 0.01010(13) 0.01382(13) 0.00165(9) 0.00441(10) 0.00226(9) S2 0.01255(13) 0.01032(13) 0.01327(12) -0.00167(9) 0.00295(9) -0.00091(9) O11 0.0176(4) 0.0128(4) 0.0235(4) 0.0035(3) 0.0087(3) -0.0001(3) O12 0.0287(5) 0.0166(4) 0.0129(4) 0.0009(3) 0.0026(3) 0.0058(4) O21 0.0161(4) 0.0172(4) 0.0173(4) -0.0026(3) -0.0015(3) 0.0004(3) O22 0.0178(4) 0.0143(4) 0.0183(4) -0.0006(3) 0.0074(3) -0.0029(3) C1 0.0126(5) 0.0100(5) 0.0142(5) 0.0004(4) 0.0044(4) 0.0013(4) C2 0.0129(5) 0.0121(5) 0.0130(5) -0.0002(4) 0.0024(4) 0.0014(4) C3 0.0123(5) 0.0099(5) 0.0130(5) -0.0011(4) 0.0032(4) -0.0001(4) C111 0.0142(5) 0.0145(5) 0.0163(5) 0.0017(4) 0.0037(4) 0.0027(4) C112 0.0192(6) 0.0179(6) 0.0275(6) -0.0020(5) 0.0052(5) -0.0009(5) C113 0.0166(6) 0.0297(7) 0.0328(7) 0.0000(6) 0.0066(5) -0.0028(5) C114 0.0169(6) 0.0306(7) 0.0271(6) 0.0011(5) 0.0077(5) 0.0062(5) C115 0.0206(6) 0.0208(6) 0.0264(6) -0.0021(5) 0.0065(5) 0.0069(5) C116 0.0168(6) 0.0153(5) 0.0208(6) 0.0004(4) 0.0048(4) 0.0019(4) C211 0.0150(5) 0.0114(5) 0.0125(5) -0.0015(4) 0.0037(4) -0.0002(4) C212 0.0228(6) 0.0124(5) 0.0222(6) 0.0003(4) 0.0105(5) 0.0003(4) C213 0.0278(7) 0.0125(5) 0.0298(7) -0.0020(5) 0.0130(6) 0.0026(5) C214 0.0236(6) 0.0205(6) 0.0242(6) -0.0045(5) 0.0117(5) 0.0013(5) C215 0.0254(7) 0.0197(6) 0.0236(6) 0.0019(5) 0.0134(5) -0.0004(5) C216 0.0225(6) 0.0126(5) 0.0216(6) 0.0020(4) 0.0099(5) -0.0004(4) O31 0.0393(6) 0.0256(5) 0.0344(6) -0.0060(4) 0.0211(5) -0.0024(5) C31 0.0177(6) 0.0182(6) 0.0264(6) -0.0020(5) 0.0083(5) -0.0018(5) C32 0.0436(9) 0.0183(6) 0.0240(7) 0.0011(5) 0.0108(6) 0.0033(6) C33 0.0368(8) 0.0280(7) 0.0207(6) 0.0030(5) 0.0077(6) 0.0056(6) C34 0.0268(7) 0.0395(9) 0.0234(6) 0.0003(6) 0.0101(6) -0.0020(6) C35 0.0185(6) 0.0310(7) 0.0196(6) -0.0052(5) 0.0017(5) 0.0058(5) C36 0.0277(7) 0.0255(7) 0.0228(6) 0.0025(5) 0.0071(5) 0.0067(5) C37 0.0279(7) 0.0167(6) 0.0343(7) 0.0019(5) 0.0170(6) -0.0013(5) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 S1 O11 1.4368(9) . ? S1 O12 1.4411(9) . ? S1 C111 1.7644(12) . ? S1 C1 1.8050(11) . ? S2 O22 1.4399(9) . ? S2 O21 1.4431(9) . ? S2 C211 1.7599(12) . ? S2 C3 1.8015(11) . ? C1 C2 1.3972(16) . ? C1 C1 1.401(2) 2_656 ? C2 C3 1.3935(15) . ? C2 H2 0.95 . ? C3 C3 1.399(2) 2_656 ? C111 C116 1.3916(17) . ? C111 C112 1.3961(18) . ? C112 C113 1.3896(19) . ? C112 H112 0.95 . ? C113 C114 1.394(2) . ? C113 H113 0.95 . ? C114 C115 1.390(2) . ? C114 H114 0.95 . ? C115 C116 1.3907(18) . ? C115 H115 0.95 . ? C116 H116 0.95 . ? C211 C212 1.3890(16) . ? C211 C216 1.3911(16) . ? C212 C213 1.3884(17) . ? C212 H212 0.95 . ? C213 C214 1.3905(19) . ? C213 H213 0.95 . ? C214 C215 1.3919(19) . ? C214 H214 0.95 . ? C215 C216 1.3913(17) . ? C215 H215 0.95 . ? C216 H216 0.95 . ? O31 C31 1.2201(16) . ? C31 C37 1.5099(19) . ? C31 C32 1.5161(19) . ? C32 C33 1.526(2) . ? C32 H32A 0.99 . ? C32 H32B 0.99 . ? C33 C34 1.535(2) . ? C33 H33A 0.99 . ? C33 H33B 0.99 . ? C34 C35 1.521(2) . ? C34 H34A 0.99 . ? C34 H34B 0.99 . ? C35 C36 1.5237(19) . ? C35 H35A 0.99 . ? C35 H35B 0.99 . ? C36 C37 1.535(2) . ? C36 H36A 0.99 . ? C36 H36B 0.99 . ? C37 H37A 0.99 . ? C37 H37B 0.99 . ? 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 O11 S1 O12 118.96(6) . . ? O11 S1 C111 109.44(6) . . ? O12 S1 C111 107.58(6) . . ? O11 S1 C1 109.05(5) . . ? O12 S1 C1 104.86(5) . . ? C111 S1 C1 106.19(5) . . ? O22 S2 O21 118.74(6) . . ? O22 S2 C211 109.74(5) . . ? O21 S2 C211 107.59(5) . . ? O22 S2 C3 108.17(5) . . ? O21 S2 C3 105.03(5) . . ? C211 S2 C3 106.92(5) . . ? C2 C1 C1 119.16(7) . 2_656 ? C2 C1 S1 113.63(8) . . ? C1 C1 S1 127.17(4) 2_656 . ? C3 C2 C1 121.55(11) . . ? C3 C2 H2 119.2 . . ? C1 C2 H2 119.2 . . ? C2 C3 C3 119.28(7) . 2_656 ? C2 C3 S2 114.84(9) . . ? C3 C3 S2 125.82(4) 2_656 . ? C116 C111 C112 121.48(11) . . ? C116 C111 S1 119.22(9) . . ? C112 C111 S1 119.15(9) . . ? C113 C112 C111 119.07(12) . . ? C113 C112 H112 120.5 . . ? C111 C112 H112 120.5 . . ? C112 C113 C114 119.95(13) . . ? C112 C113 H113 120 . . ? C114 C113 H113 120 . . ? C115 C114 C113 120.33(12) . . ? C115 C114 H114 119.8 . . ? C113 C114 H114 119.8 . . ? C114 C115 C116 120.44(13) . . ? C114 C115 H115 119.8 . . ? C116 C115 H115 119.8 . . ? C115 C116 C111 118.73(12) . . ? C115 C116 H116 120.6 . . ? C111 C116 H116 120.6 . . ? C212 C211 C216 121.87(11) . . ? C212 C211 S2 118.02(9) . . ? C216 C211 S2 119.79(9) . . ? C213 C212 C211 118.78(11) . . ? C213 C212 H212 120.6 . . ? C211 C212 H212 120.6 . . ? C212 C213 C214 120.13(12) . . ? C212 C213 H213 119.9 . . ? C214 C213 H213 119.9 . . ? C213 C214 C215 120.48(12) . . ? C213 C214 H214 119.8 . . ? C215 C214 H214 119.8 . . ? C216 C215 C214 119.98(12) . . ? C216 C215 H215 120 . . ? C214 C215 H215 120 . . ? C211 C216 C215 118.71(11) . . ? C211 C216 H216 120.6 . . ? C215 C216 H216 120.6 . . ? O31 C31 C37 120.76(13) . . ? O31 C31 C32 119.00(12) . . ? C37 C31 C32 120.25(12) . . ? C31 C32 C33 118.80(12) . . ? C31 C32 H32A 107.6 . . ? C33 C32 H32A 107.6 . . ? C31 C32 H32B 107.6 . . ? C33 C32 H32B 107.6 . . ? H32A C32 H32B 107 . . ? C32 C33 C34 115.12(13) . . ? C32 C33 H33A 108.5 . . ? C34 C33 H33A 108.5 . . ? C32 C33 H33B 108.5 . . ? C34 C33 H33B 108.5 . . ? H33A C33 H33B 107.5 . . ? C35 C34 C33 114.51(12) . . ? C35 C34 H34A 108.6 . . ? C33 C34 H34A 108.6 . . ? C35 C34 H34B 108.6 . . ? C33 C34 H34B 108.6 . . ? H34A C34 H34B 107.6 . . ? C34 C35 C36 114.89(12) . . ? C34 C35 H35A 108.5 . . ? C36 C35 H35A 108.5 . . ? C34 C35 H35B 108.5 . . ? C36 C35 H35B 108.5 . . ? H35A C35 H35B 107.5 . . ? C35 C36 C37 115.21(12) . . ? C35 C36 H36A 108.5 . . ? C37 C36 H36A 108.5 . . ? C35 C36 H36B 108.5 . . ? C37 C36 H36B 108.5 . . ? H36A C36 H36B 107.5 . . ? C31 C37 C36 113.91(12) . . ? C31 C37 H37A 108.8 . . ? C36 C37 H37A 108.8 . . ? C31 C37 H37B 108.8 . . ? C36 C37 H37B 108.8 . . ? H37A C37 H37B 107.7 . . ? 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 O11 S1 C1 C2 145.12(9) . . . . ? O12 S1 C1 C2 16.69(10) . . . . ? C111 S1 C1 C2 -97.04(9) . . . . ? O11 S1 C1 C1 -32.76(15) . . . 2_656 ? O12 S1 C1 C1 -161.19(14) . . . 2_656 ? C111 S1 C1 C1 85.08(15) . . . 2_656 ? C1 C1 C2 C3 0.3(2) 2_656 . . . ? S1 C1 C2 C3 -177.77(9) . . . . ? C1 C2 C3 C3 0.6(2) . . . 2_656 ? C1 C2 C3 S2 -176.57(9) . . . . ? O22 S2 C3 C2 136.61(9) . . . . ? O21 S2 C3 C2 8.87(10) . . . . ? C211 S2 C3 C2 -105.27(9) . . . . ? O22 S2 C3 C3 -40.37(15) . . . 2_656 ? O21 S2 C3 C3 -168.11(13) . . . 2_656 ? C211 S2 C3 C3 77.75(14) . . . 2_656 ? O11 S1 C111 C116 0.33(12) . . . . ? O12 S1 C111 C116 130.90(10) . . . . ? C1 S1 C111 C116 -117.25(10) . . . . ? O11 S1 C111 C112 -175.28(10) . . . . ? O12 S1 C111 C112 -44.71(12) . . . . ? C1 S1 C111 C112 67.14(11) . . . . ? C116 C111 C112 C113 -0.1(2) . . . . ? S1 C111 C112 C113 175.41(11) . . . . ? C111 C112 C113 C114 -0.5(2) . . . . ? C112 C113 C114 C115 0.7(2) . . . . ? C113 C114 C115 C116 -0.2(2) . . . . ? C114 C115 C116 C111 -0.4(2) . . . . ? C112 C111 C116 C115 0.58(19) . . . . ? S1 C111 C116 C115 -174.93(10) . . . . ? O22 S2 C211 C212 -16.97(12) . . . . ? O21 S2 C211 C212 113.55(10) . . . . ? C3 S2 C211 C212 -134.05(10) . . . . ? O22 S2 C211 C216 169.37(10) . . . . ? O21 S2 C211 C216 -60.11(11) . . . . ? C3 S2 C211 C216 52.28(11) . . . . ? C216 C211 C212 C213 2.1(2) . . . . ? S2 C211 C212 C213 -171.42(11) . . . . ? C211 C212 C213 C214 -1.1(2) . . . . ? C212 C213 C214 C215 -0.9(2) . . . . ? C213 C214 C215 C216 1.8(2) . . . . ? C212 C211 C216 C215 -1.1(2) . . . . ? S2 C211 C216 C215 172.28(10) . . . . ? C214 C215 C216 C211 -0.8(2) . . . . ? O31 C31 C32 C33 179.80(15) . . . . ? C37 C31 C32 C33 -0.3(2) . . . . ? C31 C32 C33 C34 64.3(2) . . . . ? C32 C33 C34 C35 -81.01(17) . . . . ? C33 C34 C35 C36 63.85(17) . . . . ? C34 C35 C36 C37 -65.39(17) . . . . ? O31 C31 C37 C36 116.55(15) . . . . ? C32 C31 C37 C36 -63.30(19) . . . . ? C35 C36 C37 C31 82.06(17) . . . . ? # END of CIF