# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # 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_ohj191_0m _database_code_depnum_ccdc_archive 'CCDC 898465' #TrackingRef '13567_web_deposit_cif_file_0_JosephHarrity_1346140167.ohj191_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H12 O4 ' _chemical_formula_sum 'C9 H12 O4' _chemical_formula_weight 184.19 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.4701(6) _cell_length_b 10.1349(10) _cell_length_c 14.1595(13) _cell_angle_alpha 93.806(6) _cell_angle_beta 91.027(6) _cell_angle_gamma 105.958(6) _cell_volume 890.11(15) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6872 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 27.54 _exptl_crystal_description PLATE _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.374 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9662 _exptl_absorpt_correction_T_max 0.9903 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4104 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0300 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.44 _diffrn_reflns_theta_max 27.55 _reflns_number_total 4104 _reflns_number_gt 3588 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0739P)^2^+0.5602P] 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 4104 _refine_ls_number_parameters 240 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0543 _refine_ls_R_factor_gt 0.0443 _refine_ls_wR_factor_ref 0.1240 _refine_ls_wR_factor_gt 0.1163 _refine_ls_goodness_of_fit_ref 0.943 _refine_ls_restrained_S_all 0.943 _refine_ls_shift/su_max 0.003 _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 O1 O 0.0083(2) 0.67272(15) 0.97629(10) 0.0164(3) Uani 1 1 d . . . O2 O 0.3241(3) 0.55537(16) 0.89003(11) 0.0222(4) Uani 1 1 d . . . H2 H 0.4253 0.5237 0.9005 0.033 Uiso 1 1 calc R . . O3 O 0.3286(2) 0.54538(15) 1.07979(11) 0.0189(3) Uani 1 1 d . . . H3 H 0.2277 0.4883 1.0517 0.028 Uiso 1 1 calc R . . O4 O 0.2962(3) 0.99528(17) 0.92013(13) 0.0274(4) Uani 1 1 d . . . C1 C 0.1701(3) 0.7430(2) 0.91338(15) 0.0162(4) Uani 1 1 d . . . C2 C 0.3619(3) 0.6860(2) 0.93913(14) 0.0166(4) Uani 1 1 d . . . H2A H 0.4998 0.7483 0.9235 0.020 Uiso 1 1 calc R . . C3 C 0.3402(3) 0.6776(2) 1.04957(14) 0.0159(4) Uani 1 1 d . . . H3A H 0.4611 0.7461 1.0828 0.019 Uiso 1 1 calc R . . C4 C 0.1299(3) 0.7194(2) 1.06539(14) 0.0166(4) Uani 1 1 d . . . H4 H 0.0530 0.6819 1.1210 0.020 Uiso 1 1 calc R . . C5 C 0.1750(4) 0.8754(2) 1.06368(16) 0.0212(5) Uani 1 1 d . . . H5A H 0.0504 0.9063 1.0806 0.025 Uiso 1 1 calc R . . H5B H 0.2970 0.9242 1.1051 0.025 Uiso 1 1 calc R . . C6 C 0.2247(3) 0.8910(2) 0.95954(16) 0.0199(5) Uani 1 1 d . . . C7 C 0.0929(4) 0.7246(3) 0.81026(15) 0.0223(5) Uani 1 1 d . . . H7A H 0.0922 0.6333 0.7845 0.027 Uiso 1 1 calc R . . H7B H 0.1928 0.7911 0.7748 0.027 Uiso 1 1 calc R . . C8 C -0.1311(4) 0.7427(3) 0.79736(17) 0.0273(5) Uani 1 1 d . . . H8 H -0.2473 0.6711 0.8126 0.033 Uiso 1 1 calc R . . C9 C -0.1718(4) 0.8517(3) 0.76642(18) 0.0326(5) Uani 1 1 d . . . H9A H -0.0595 0.9252 0.7505 0.039 Uiso 1 1 calc R . . H9B H -0.3132 0.8558 0.7603 0.039 Uiso 1 1 calc R . . O1A O 0.4882(2) 0.81918(15) 0.47780(10) 0.0154(3) Uani 1 1 d . . . O2A O 0.1589(2) 0.92373(16) 0.39828(11) 0.0187(3) Uani 1 1 d . . . H2A1 H 0.0563 0.9554 0.4063 0.028 Uiso 1 1 calc R . . O3A O 0.1933(2) 0.97157(15) 0.58780(11) 0.0182(3) Uani 1 1 d . . . H3A1 H 0.2883 1.0232 0.5595 0.027 Uiso 1 1 calc R . . O4A O 0.1827(3) 0.48583(16) 0.42557(12) 0.0250(4) Uani 1 1 d . . . C1A C 0.3081(3) 0.7364(2) 0.41746(14) 0.0140(4) Uani 1 1 d . . . C2A C 0.1273(3) 0.8023(2) 0.44607(14) 0.0149(4) Uani 1 1 d . . . H2A2 H -0.0159 0.7389 0.4317 0.018 Uiso 1 1 calc R . . C3A C 0.1761(3) 0.8333(2) 0.55626(14) 0.0149(4) Uani 1 1 d . . . H3A2 H 0.0631 0.7716 0.5904 0.018 Uiso 1 1 calc R . . C4A C 0.3880(3) 0.7937(2) 0.56849(15) 0.0174(4) Uani 1 1 d . . . H4A H 0.4789 0.8430 0.6229 0.021 Uiso 1 1 calc R . . C5A C 0.3394(4) 0.6362(2) 0.56711(16) 0.0208(4) Uani 1 1 d . . . H5A1 H 0.4671 0.6078 0.5816 0.025 Uiso 1 1 calc R . . H5A2 H 0.2278 0.5976 0.6103 0.025 Uiso 1 1 calc R . . C6A C 0.2627(3) 0.5985(2) 0.46392(16) 0.0177(4) Uani 1 1 d . . . C7A C 0.3594(3) 0.7321(2) 0.31333(14) 0.0181(4) Uani 1 1 d . . . H7A1 H 0.2334 0.6761 0.2772 0.022 Uiso 1 1 calc R . . H7A2 H 0.3906 0.8246 0.2925 0.022 Uiso 1 1 calc R . . C8A C 0.5458(4) 0.6757(3) 0.29215(15) 0.0239(5) Uani 1 1 d . . . H8A H 0.5325 0.5844 0.3034 0.029 Uiso 1 1 calc R . . C9A C 0.7287(4) 0.7478(3) 0.25831(17) 0.0348(6) Uani 1 1 d . . . H9A1 H 0.7468 0.8393 0.2463 0.042 Uiso 1 1 calc R . . H9A2 H 0.8388 0.7069 0.2466 0.042 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 O1 0.0148(7) 0.0192(8) 0.0154(7) 0.0024(6) 0.0009(6) 0.0048(6) O2 0.0231(8) 0.0236(9) 0.0242(8) -0.0038(6) -0.0033(6) 0.0149(7) O3 0.0190(8) 0.0136(8) 0.0236(8) 0.0024(6) -0.0049(6) 0.0040(6) O4 0.0237(8) 0.0195(8) 0.0396(10) 0.0094(7) -0.0020(8) 0.0058(7) C1 0.0137(9) 0.0180(11) 0.0190(10) 0.0051(8) 0.0036(8) 0.0066(8) C2 0.0159(10) 0.0170(10) 0.0191(10) 0.0029(8) 0.0020(8) 0.0076(8) C3 0.0150(10) 0.0149(10) 0.0187(10) 0.0012(8) -0.0009(8) 0.0058(8) C4 0.0151(10) 0.0192(11) 0.0160(10) 0.0006(8) -0.0008(7) 0.0058(8) C5 0.0225(11) 0.0197(11) 0.0237(11) -0.0028(9) -0.0006(9) 0.0107(9) C6 0.0153(10) 0.0204(11) 0.0268(12) 0.0026(9) -0.0020(8) 0.0095(8) C7 0.0253(12) 0.0305(12) 0.0160(10) 0.0045(9) 0.0035(8) 0.0150(9) C8 0.0281(12) 0.0362(13) 0.0208(11) 0.0018(9) -0.0016(9) 0.0143(10) C9 0.0342(13) 0.0401(14) 0.0261(12) 0.0042(11) -0.0016(10) 0.0143(11) O1A 0.0112(7) 0.0156(7) 0.0184(7) 0.0012(5) 0.0004(5) 0.0018(6) O2A 0.0202(8) 0.0168(7) 0.0227(8) 0.0072(6) 0.0051(6) 0.0098(6) O3A 0.0187(8) 0.0124(7) 0.0234(8) 0.0001(6) 0.0049(6) 0.0042(6) O4A 0.0247(8) 0.0142(8) 0.0350(9) -0.0012(7) 0.0091(7) 0.0039(6) C1A 0.0130(10) 0.0118(9) 0.0170(10) 0.0009(7) 0.0016(7) 0.0029(7) C2A 0.0134(9) 0.0126(10) 0.0191(10) 0.0017(7) 0.0021(7) 0.0039(7) C3A 0.0152(9) 0.0106(9) 0.0183(10) 0.0000(7) 0.0015(8) 0.0030(7) C4A 0.0156(10) 0.0190(11) 0.0180(10) 0.0012(8) -0.0001(8) 0.0056(8) C5A 0.0227(11) 0.0184(11) 0.0241(10) 0.0069(9) 0.0045(9) 0.0087(9) C6A 0.0149(10) 0.0158(10) 0.0242(11) 0.0038(8) 0.0050(8) 0.0065(8) C7A 0.0177(10) 0.0200(10) 0.0166(9) 0.0001(8) 0.0002(8) 0.0058(8) C8A 0.0272(12) 0.0353(13) 0.0155(10) 0.0015(9) 0.0029(8) 0.0189(10) C9A 0.0200(11) 0.0609(18) 0.0219(12) -0.0140(11) -0.0001(9) 0.0127(11) _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 O1 C1 1.451(2) . ? O1 C4 1.454(2) . ? O2 C2 1.411(3) . ? O2 H2 0.8200 . ? O3 C3 1.416(2) . ? O3 H3 0.8200 . ? O4 C6 1.209(3) . ? C1 C7 1.518(3) . ? C1 C6 1.541(3) . ? C1 C2 1.553(3) . ? C2 C3 1.578(3) . ? C2 H2A 0.9800 . ? C3 C4 1.548(3) . ? C3 H3A 0.9800 . ? C4 C5 1.529(3) . ? C4 H4 0.9800 . ? C5 C6 1.524(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C7 C8 1.520(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.304(4) . ? C8 H8 0.9300 . ? C9 H9A 0.9300 . ? C9 H9B 0.9300 . ? O1A C4A 1.455(2) . ? O1A C1A 1.457(2) . ? O2A C2A 1.411(2) . ? O2A H2A1 0.8200 . ? O3A C3A 1.416(2) . ? O3A H3A1 0.8200 . ? O4A C6A 1.204(3) . ? C1A C7A 1.518(3) . ? C1A C6A 1.541(3) . ? C1A C2A 1.545(3) . ? C2A C3A 1.580(3) . ? C2A H2A2 0.9800 . ? C3A C4A 1.541(3) . ? C3A H3A2 0.9800 . ? C4A C5A 1.538(3) . ? C4A H4A 0.9800 . ? C5A C6A 1.524(3) . ? C5A H5A1 0.9700 . ? C5A H5A2 0.9700 . ? C7A C8A 1.497(3) . ? C7A H7A1 0.9700 . ? C7A H7A2 0.9700 . ? C8A C9A 1.325(4) . ? C8A H8A 0.9300 . ? C9A H9A1 0.9300 . ? C9A H9A2 0.9300 . ? 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 O1 C4 98.08(15) . . ? C2 O2 H2 109.5 . . ? C3 O3 H3 109.5 . . ? O1 C1 C7 113.38(17) . . ? O1 C1 C6 100.48(16) . . ? C7 C1 C6 115.81(18) . . ? O1 C1 C2 101.47(16) . . ? C7 C1 C2 117.17(17) . . ? C6 C1 C2 106.35(17) . . ? O2 C2 C1 107.07(17) . . ? O2 C2 C3 112.66(17) . . ? C1 C2 C3 101.31(16) . . ? O2 C2 H2A 111.8 . . ? C1 C2 H2A 111.8 . . ? C3 C2 H2A 111.8 . . ? O3 C3 C4 112.64(17) . . ? O3 C3 C2 113.34(16) . . ? C4 C3 C2 101.45(15) . . ? O3 C3 H3A 109.7 . . ? C4 C3 H3A 109.7 . . ? C2 C3 H3A 109.7 . . ? O1 C4 C5 101.13(17) . . ? O1 C4 C3 103.28(15) . . ? C5 C4 C3 109.76(17) . . ? O1 C4 H4 113.8 . . ? C5 C4 H4 113.8 . . ? C3 C4 H4 113.8 . . ? C6 C5 C4 99.63(17) . . ? C6 C5 H5A 111.8 . . ? C4 C5 H5A 111.8 . . ? C6 C5 H5B 111.8 . . ? C4 C5 H5B 111.8 . . ? H5A C5 H5B 109.6 . . ? O4 C6 C5 128.6(2) . . ? O4 C6 C1 126.2(2) . . ? C5 C6 C1 105.20(17) . . ? C1 C7 C8 112.53(17) . . ? C1 C7 H7A 109.1 . . ? C8 C7 H7A 109.1 . . ? C1 C7 H7B 109.1 . . ? C8 C7 H7B 109.1 . . ? H7A C7 H7B 107.8 . . ? C9 C8 C7 124.6(2) . . ? C9 C8 H8 117.7 . . ? C7 C8 H8 117.7 . . ? C8 C9 H9A 120.0 . . ? C8 C9 H9B 120.0 . . ? H9A C9 H9B 120.0 . . ? C4A O1A C1A 97.68(14) . . ? C2A O2A H2A1 109.5 . . ? C3A O3A H3A1 109.5 . . ? O1A C1A C7A 112.92(16) . . ? O1A C1A C6A 100.36(16) . . ? C7A C1A C6A 116.11(17) . . ? O1A C1A C2A 101.58(15) . . ? C7A C1A C2A 116.78(17) . . ? C6A C1A C2A 106.95(16) . . ? O2A C2A C1A 107.28(16) . . ? O2A C2A C3A 112.24(16) . . ? C1A C2A C3A 101.05(16) . . ? O2A C2A H2A2 111.9 . . ? C1A C2A H2A2 111.9 . . ? C3A C2A H2A2 111.9 . . ? O3A C3A C4A 113.33(16) . . ? O3A C3A C2A 113.18(17) . . ? C4A C3A C2A 101.68(16) . . ? O3A C3A H3A2 109.5 . . ? C4A C3A H3A2 109.5 . . ? C2A C3A H3A2 109.5 . . ? O1A C4A C5A 100.99(16) . . ? O1A C4A C3A 103.66(16) . . ? C5A C4A C3A 109.50(17) . . ? O1A C4A H4A 113.8 . . ? C5A C4A H4A 113.8 . . ? C3A C4A H4A 113.8 . . ? C6A C5A C4A 99.34(17) . . ? C6A C5A H5A1 111.9 . . ? C4A C5A H5A1 111.9 . . ? C6A C5A H5A2 111.9 . . ? C4A C5A H5A2 111.9 . . ? H5A1 C5A H5A2 109.6 . . ? O4A C6A C5A 128.2(2) . . ? O4A C6A C1A 126.4(2) . . ? C5A C6A C1A 105.39(17) . . ? C8A C7A C1A 113.64(17) . . ? C8A C7A H7A1 108.8 . . ? C1A C7A H7A1 108.8 . . ? C8A C7A H7A2 108.8 . . ? C1A C7A H7A2 108.8 . . ? H7A1 C7A H7A2 107.7 . . ? C9A C8A C7A 124.0(2) . . ? C9A C8A H8A 118.0 . . ? C7A C8A H8A 118.0 . . ? C8A C9A H9A1 120.0 . . ? C8A C9A H9A2 120.0 . . ? H9A1 C9A H9A2 120.0 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.55 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.680 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.059 data_shelxl _database_code_depnum_ccdc_archive 'CCDC 898466' #TrackingRef '13568_web_deposit_cif_file_1_JosephHarrity_1346140167.ohj182_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H26 O4 Si' _chemical_formula_weight 298.45 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' Si Si 0.0817 0.0704 '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 7.3493(12) _cell_length_b 9.3408(15) _cell_length_c 25.042(4) _cell_angle_alpha 73.729(6) _cell_angle_beta 88.572(6) _cell_angle_gamma 86.474(6) _cell_volume 1647.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3417 _cell_measurement_theta_min 2.19 _cell_measurement_theta_max 24.66 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.204 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.153 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9701 _exptl_absorpt_correction_T_max 0.9879 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 100 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 5771 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1011 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 0.85 _diffrn_reflns_theta_max 27.54 _reflns_number_total 5771 _reflns_number_gt 3964 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1053P)^2^+2.3595P] 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 5771 _refine_ls_number_parameters 374 _refine_ls_number_restraints 194 _refine_ls_R_factor_all 0.1199 _refine_ls_R_factor_gt 0.0727 _refine_ls_wR_factor_ref 0.2182 _refine_ls_wR_factor_gt 0.1868 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.062 _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 Si1 Si 1.0208(2) 0.6187(2) 0.19398(7) 0.0227(4) Uani 1 1 d . . . Si1A Si 0.4251(2) 0.9843(2) 0.35203(7) 0.0196(4) Uani 1 1 d . . . C1 C 0.9212(8) 1.0289(7) 0.1149(3) 0.0235(10) Uani 1 1 d U . . H1 H 1.0219 1.0350 0.1401 0.028 Uiso 1 1 calc R . . C1A C 0.5351(8) 0.8062(7) 0.5053(2) 0.0189(9) Uani 1 1 d U . . H1A H 0.4262 0.8739 0.5076 0.023 Uiso 1 1 calc R . . C2 C 0.9473(8) 1.1211(7) 0.0546(3) 0.0243(10) Uani 1 1 d U . . H2B H 0.9916 1.2206 0.0523 0.029 Uiso 1 1 calc R . . H2C H 1.0325 1.0688 0.0341 0.029 Uiso 1 1 calc R . . C2A C 0.5836(8) 0.7997(7) 0.4455(2) 0.0197(9) Uani 1 1 d U . . H2A1 H 0.5118 0.7249 0.4346 0.024 Uiso 1 1 calc R . . C3 C 0.7533(9) 1.1328(7) 0.0331(3) 0.0238(10) Uani 1 1 d U . . C3A C 0.7884(8) 0.7487(7) 0.4522(2) 0.0191(9) Uani 1 1 d U . . H3A H 0.8632 0.8293 0.4288 0.023 Uiso 1 1 calc R . . C4 C 0.6421(8) 1.0640(7) 0.0850(3) 0.0234(9) Uani 1 1 d U . . C4A C 0.8236(8) 0.7309(7) 0.5142(2) 0.0186(8) Uani 1 1 d U . . C5 C 0.6781(8) 0.8901(7) 0.0964(3) 0.0226(9) Uani 1 1 d U . . H5 H 0.5949 0.8362 0.1265 0.027 Uiso 1 1 calc R . . C5A C 0.7246(8) 0.5932(7) 0.5456(2) 0.0190(9) Uani 1 1 d U . . C6 C 0.8777(8) 0.8665(7) 0.1170(3) 0.0232(10) Uani 1 1 d U . . H6 H 0.9596 0.8264 0.0914 0.028 Uiso 1 1 calc R . . C6A C 0.5245(8) 0.6470(7) 0.5438(2) 0.0189(9) Uani 1 1 d U . . H6A1 H 0.4773 0.6471 0.5812 0.023 Uiso 1 1 calc R . . H6A2 H 0.4480 0.5858 0.5279 0.023 Uiso 1 1 calc R . . C7 C 1.2488(9) 0.6450(8) 0.1589(3) 0.0353(17) Uani 1 1 d . . . H7A H 1.2326 0.6786 0.1185 0.053 Uiso 1 1 calc R . . H7B H 1.3218 0.5501 0.1689 0.053 Uiso 1 1 calc R . . H7C H 1.3116 0.7202 0.1709 0.053 Uiso 1 1 calc R . . C7A C 0.1967(9) 0.9144(8) 0.3732(3) 0.0295(15) Uani 1 1 d . . . H7A1 H 0.2064 0.8052 0.3871 0.044 Uiso 1 1 calc R . . H7A2 H 0.1152 0.9446 0.3411 0.044 Uiso 1 1 calc R . . H7A3 H 0.1475 0.9563 0.4027 0.044 Uiso 1 1 calc R . . C8 C 1.0416(9) 0.5910(8) 0.2699(3) 0.0308(16) Uani 1 1 d . . . H8A H 1.0835 0.6819 0.2766 0.046 Uiso 1 1 calc R . . H8B H 1.1296 0.5073 0.2853 0.046 Uiso 1 1 calc R . . H8C H 0.9225 0.5691 0.2879 0.046 Uiso 1 1 calc R . . C8A C 0.4086(9) 1.1921(7) 0.3283(3) 0.0261(14) Uani 1 1 d . . . H8A1 H 0.3356 1.2306 0.3550 0.039 Uiso 1 1 calc R . . H8A2 H 0.3504 1.2255 0.2917 0.039 Uiso 1 1 calc R . . H8A3 H 0.5311 1.2296 0.3255 0.039 Uiso 1 1 calc R . . C9 C 0.9105(9) 0.4558(7) 0.1790(3) 0.0271(12) Uani 1 1 d U . . C9A C 0.5289(9) 0.9028(8) 0.2962(3) 0.0285(12) Uani 1 1 d U . . C10 C 1.0282(9) 0.3117(7) 0.2019(3) 0.0323(14) Uani 1 1 d U . . H10A H 0.9710 0.2285 0.1935 0.048 Uiso 1 1 calc R . . H10B H 1.0394 0.2915 0.2423 0.048 Uiso 1 1 calc R . . H10C H 1.1495 0.3226 0.1846 0.048 Uiso 1 1 calc R . . C10A C 0.5345(10) 0.7321(8) 0.3137(3) 0.0323(14) Uani 1 1 d U . . H10D H 0.5888 0.6948 0.2837 0.048 Uiso 1 1 calc R . . H10E H 0.4102 0.6986 0.3213 0.048 Uiso 1 1 calc R . . H10F H 0.6080 0.6933 0.3473 0.048 Uiso 1 1 calc R . . C11 C 0.7215(9) 0.4385(8) 0.2081(3) 0.0332(14) Uani 1 1 d U . . H11A H 0.6463 0.5315 0.1946 0.050 Uiso 1 1 calc R . . H11B H 0.7372 0.4165 0.2484 0.050 Uiso 1 1 calc R . . H11C H 0.6615 0.3565 0.1998 0.050 Uiso 1 1 calc R . . C11A C 0.7233(9) 0.9549(8) 0.2826(3) 0.0340(14) Uani 1 1 d U . . H11D H 0.8005 0.9140 0.3153 0.051 Uiso 1 1 calc R . . H11E H 0.7203 1.0642 0.2723 0.051 Uiso 1 1 calc R . . H11F H 0.7729 0.9196 0.2516 0.051 Uiso 1 1 calc R . . C12 C 0.8853(10) 0.4812(8) 0.1171(3) 0.0326(14) Uani 1 1 d U . . H12A H 0.8100 0.5735 0.1021 0.049 Uiso 1 1 calc R . . H12B H 0.8250 0.3968 0.1107 0.049 Uiso 1 1 calc R . . H12C H 1.0046 0.4897 0.0984 0.049 Uiso 1 1 calc R . . C12A C 0.4121(10) 0.9608(8) 0.2428(3) 0.0344(15) Uani 1 1 d U . . H12D H 0.4654 0.9202 0.2135 0.052 Uiso 1 1 calc R . . H12E H 0.4098 1.0702 0.2304 0.052 Uiso 1 1 calc R . . H12F H 0.2875 0.9287 0.2509 0.052 Uiso 1 1 calc R . . C13 C 0.4433(8) 1.1201(7) 0.0858(3) 0.0253(10) Uani 1 1 d U . . H13C H 0.3803 1.1045 0.0535 0.030 Uiso 1 1 calc R . . H13D H 0.3837 1.0606 0.1200 0.030 Uiso 1 1 calc R . . C13A C 1.0174(8) 0.7402(7) 0.5304(2) 0.0206(9) Uani 1 1 d U . . H13A H 1.0960 0.6677 0.5168 0.025 Uiso 1 1 calc R . . H13B H 1.0576 0.8413 0.5116 0.025 Uiso 1 1 calc R . . C14 C 0.4218(9) 1.2831(8) 0.0836(3) 0.0283(11) Uani 1 1 d U . . H14 H 0.4645 1.3116 0.1145 0.034 Uiso 1 1 calc R . . C14A C 1.0451(8) 0.7096(7) 0.5916(3) 0.0241(11) Uani 1 1 d U . . H14A H 0.9996 0.6205 0.6152 0.029 Uiso 1 1 calc R . . C15 C 0.3485(10) 1.3885(9) 0.0424(3) 0.0367(15) Uani 1 1 d U . . H15C H 0.3043 1.3642 0.0108 0.044 Uiso 1 1 calc R . . H15D H 0.3396 1.4891 0.0440 0.044 Uiso 1 1 calc R . . C15A C 1.1272(9) 0.7962(8) 0.6151(3) 0.0287(13) Uani 1 1 d U . . H15A H 1.1745 0.8863 0.5928 0.034 Uiso 1 1 calc R . . H15B H 1.1396 0.7691 0.6544 0.034 Uiso 1 1 calc R . . O1 O 0.7447(5) 1.0915(5) 0.12854(17) 0.0227(10) Uani 1 1 d . . . O1A O 0.7047(5) 0.8511(4) 0.52381(17) 0.0195(9) Uani 1 1 d . . . O2 O 0.6608(6) 0.8401(5) 0.04815(18) 0.0281(11) Uani 1 1 d . . . H2 H 0.5505 0.8282 0.0435 0.042 Uiso 1 1 calc R . . O2A O 0.8233(5) 0.6156(5) 0.43559(18) 0.0235(10) Uani 1 1 d . . . H2A H 0.9363 0.5957 0.4351 0.035 Uiso 1 1 calc R . . O3 O 0.7040(6) 1.1796(5) -0.01413(18) 0.0289(11) Uani 1 1 d . . . O3A O 0.7898(6) 0.4683(5) 0.56491(17) 0.0226(10) Uani 1 1 d . . . O4 O 0.8874(6) 0.7736(5) 0.17178(17) 0.0256(10) Uani 1 1 d . . . O4A O 0.5599(5) 0.9422(5) 0.40715(16) 0.0207(9) 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 Si1 0.0203(9) 0.0235(10) 0.0235(9) -0.0046(8) -0.0044(7) -0.0026(7) Si1A 0.0179(9) 0.0178(9) 0.0221(9) -0.0036(8) -0.0036(7) -0.0015(7) C1 0.023(2) 0.024(2) 0.025(2) -0.0071(19) -0.0013(17) -0.0034(18) C1A 0.0181(19) 0.016(2) 0.0219(19) -0.0036(17) -0.0027(17) -0.0047(17) C2 0.025(2) 0.023(2) 0.025(2) -0.0071(18) -0.0028(18) -0.0026(18) C2A 0.0178(19) 0.018(2) 0.0226(19) -0.0038(17) -0.0027(17) -0.0016(17) C3 0.025(2) 0.023(2) 0.024(2) -0.0085(18) -0.0036(16) -0.0020(18) C3A 0.0184(18) 0.016(2) 0.0235(19) -0.0067(17) -0.0028(16) 0.0003(17) C4 0.0239(18) 0.0249(19) 0.0232(18) -0.0089(17) -0.0053(15) -0.0027(16) C4A 0.0191(17) 0.0139(18) 0.0236(18) -0.0066(16) -0.0024(15) 0.0009(15) C5 0.024(2) 0.024(2) 0.022(2) -0.0088(18) -0.0046(17) -0.0051(17) C5A 0.0190(19) 0.017(2) 0.022(2) -0.0072(17) -0.0021(17) -0.0012(16) C6 0.024(2) 0.024(2) 0.022(2) -0.0061(18) -0.0029(17) -0.0053(18) C6A 0.0175(19) 0.017(2) 0.022(2) -0.0039(17) -0.0009(17) -0.0036(17) C7 0.028(4) 0.036(4) 0.042(4) -0.008(4) -0.001(3) -0.009(3) C7A 0.027(4) 0.022(4) 0.036(4) -0.002(3) -0.005(3) 0.001(3) C8 0.032(4) 0.030(4) 0.029(4) -0.005(3) -0.007(3) -0.004(3) C8A 0.029(4) 0.021(4) 0.027(4) -0.004(3) -0.007(3) -0.002(3) C9 0.025(2) 0.024(3) 0.032(3) -0.006(2) -0.003(2) -0.003(2) C9A 0.034(3) 0.030(3) 0.024(2) -0.010(2) -0.002(2) -0.003(2) C10 0.031(3) 0.023(3) 0.039(3) -0.003(3) -0.003(3) -0.001(2) C10A 0.036(3) 0.032(3) 0.031(3) -0.012(3) -0.003(3) -0.002(3) C11 0.025(3) 0.029(3) 0.044(3) -0.007(3) -0.001(2) -0.005(3) C11A 0.035(3) 0.036(4) 0.033(3) -0.013(3) 0.005(3) -0.006(3) C12 0.040(3) 0.025(3) 0.034(3) -0.008(3) -0.008(3) -0.004(3) C12A 0.044(3) 0.039(4) 0.022(3) -0.010(3) -0.006(2) -0.002(3) C13 0.024(2) 0.027(2) 0.027(2) -0.0105(19) -0.0036(18) -0.0032(18) C13A 0.0204(19) 0.016(2) 0.026(2) -0.0061(18) -0.0023(17) -0.0003(17) C14 0.025(2) 0.029(2) 0.033(2) -0.012(2) -0.003(2) -0.003(2) C14A 0.023(2) 0.022(2) 0.026(2) -0.004(2) -0.0040(19) 0.000(2) C15 0.036(4) 0.032(3) 0.038(3) -0.006(3) 0.002(3) 0.001(3) C15A 0.029(3) 0.029(3) 0.029(3) -0.010(3) -0.007(2) 0.003(3) O1 0.023(2) 0.022(3) 0.025(2) -0.011(2) -0.0050(18) 0.0005(18) O1A 0.018(2) 0.014(2) 0.027(2) -0.0071(18) -0.0059(17) 0.0018(17) O2 0.029(3) 0.030(3) 0.028(2) -0.013(2) -0.009(2) 0.000(2) O2A 0.019(2) 0.023(2) 0.032(3) -0.013(2) -0.0021(19) 0.0028(18) O3 0.032(3) 0.030(3) 0.022(2) -0.002(2) -0.0053(19) -0.001(2) O3A 0.024(2) 0.013(2) 0.030(2) -0.0046(19) -0.0079(19) 0.0014(18) O4 0.029(2) 0.026(3) 0.021(2) -0.005(2) -0.0041(18) 0.002(2) O4A 0.023(2) 0.017(2) 0.022(2) -0.0045(19) -0.0055(17) -0.0002(18) _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 Si1 O4 1.663(5) . ? Si1 C8 1.854(7) . ? Si1 C7 1.870(7) . ? Si1 C9 1.897(6) . ? Si1A O4A 1.660(4) . ? Si1A C7A 1.850(7) . ? Si1A C8A 1.861(7) . ? Si1A C9A 1.894(7) . ? C1 O1 1.462(7) . ? C1 C2 1.528(9) . ? C1 C6 1.556(9) . ? C1 H1 1.0000 . ? C1A O1A 1.465(7) . ? C1A C6A 1.534(8) . ? C1A C2A 1.547(8) . ? C1A H1A 1.0000 . ? C2 C3 1.523(8) . ? C2 H2B 0.9900 . ? C2 H2C 0.9900 . ? C2A O4A 1.410(7) . ? C2A C3A 1.550(8) . ? C2A H2A1 1.0000 . ? C3 O3 1.198(7) . ? C3 C4 1.520(9) . ? C3A O2A 1.425(7) . ? C3A C4A 1.540(8) . ? C3A H3A 1.0000 . ? C4 O1 1.431(7) . ? C4 C13 1.523(9) . ? C4 C5 1.575(9) . ? C4A O1A 1.450(7) . ? C4A C13A 1.506(8) . ? C4A C5A 1.523(8) . ? C5 O2 1.423(7) . ? C5 C6 1.549(8) . ? C5 H5 1.0000 . ? C5A O3A 1.205(7) . ? C5A C6A 1.522(8) . ? C6 O4 1.404(8) . ? C6 H6 1.0000 . ? C6A H6A1 0.9900 . ? C6A H6A2 0.9900 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C7A H7A1 0.9800 . ? C7A H7A2 0.9800 . ? C7A H7A3 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C8A H8A1 0.9800 . ? C8A H8A2 0.9800 . ? C8A H8A3 0.9800 . ? C9 C12 1.516(9) . ? C9 C10 1.529(9) . ? C9 C11 1.549(9) . ? C9A C10A 1.529(9) . ? C9A C11A 1.537(9) . ? C9A C12A 1.554(9) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C10A H10D 0.9800 . ? C10A H10E 0.9800 . ? C10A H10F 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C11A H11D 0.9800 . ? C11A H11E 0.9800 . ? C11A H11F 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C12A H12D 0.9800 . ? C12A H12E 0.9800 . ? C12A H12F 0.9800 . ? C13 C14 1.507(9) . ? C13 H13C 0.9900 . ? C13 H13D 0.9900 . ? C13A C14A 1.494(8) . ? C13A H13A 0.9900 . ? C13A H13B 0.9900 . ? C14 C15 1.311(10) . ? C14 H14 0.9500 . ? C14A C15A 1.308(9) . ? C14A H14A 0.9500 . ? C15 H15C 0.9500 . ? C15 H15D 0.9500 . ? C15A H15A 0.9500 . ? C15A H15B 0.9500 . ? O2 H2 0.8400 . ? O2A H2A 0.8400 . ? 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 O4 Si1 C8 104.8(3) . . ? O4 Si1 C7 109.9(3) . . ? C8 Si1 C7 110.8(3) . . ? O4 Si1 C9 109.9(3) . . ? C8 Si1 C9 111.1(3) . . ? C7 Si1 C9 110.1(3) . . ? O4A Si1A C7A 109.6(3) . . ? O4A Si1A C8A 104.7(3) . . ? C7A Si1A C8A 109.6(3) . . ? O4A Si1A C9A 110.2(3) . . ? C7A Si1A C9A 111.2(3) . . ? C8A Si1A C9A 111.3(3) . . ? O1 C1 C2 101.3(5) . . ? O1 C1 C6 102.3(5) . . ? C2 C1 C6 110.0(5) . . ? O1 C1 H1 114.0 . . ? C2 C1 H1 114.0 . . ? C6 C1 H1 114.0 . . ? O1A C1A C6A 101.3(4) . . ? O1A C1A C2A 102.7(4) . . ? C6A C1A C2A 109.6(5) . . ? O1A C1A H1A 114.0 . . ? C6A C1A H1A 114.0 . . ? C2A C1A H1A 114.0 . . ? C3 C2 C1 100.7(5) . . ? C3 C2 H2B 111.6 . . ? C1 C2 H2B 111.6 . . ? C3 C2 H2C 111.6 . . ? C1 C2 H2C 111.6 . . ? H2B C2 H2C 109.4 . . ? O4A C2A C1A 111.0(5) . . ? O4A C2A C3A 110.8(5) . . ? C1A C2A C3A 100.5(4) . . ? O4A C2A H2A1 111.4 . . ? C1A C2A H2A1 111.4 . . ? C3A C2A H2A1 111.4 . . ? O3 C3 C4 129.0(6) . . ? O3 C3 C2 127.2(6) . . ? C4 C3 C2 103.7(5) . . ? O2A C3A C4A 114.5(5) . . ? O2A C3A C2A 110.4(4) . . ? C4A C3A C2A 103.3(5) . . ? O2A C3A H3A 109.5 . . ? C4A C3A H3A 109.5 . . ? C2A C3A H3A 109.5 . . ? O1 C4 C3 103.1(5) . . ? O1 C4 C13 112.2(5) . . ? C3 C4 C13 117.1(6) . . ? O1 C4 C5 101.3(5) . . ? C3 C4 C5 105.2(5) . . ? C13 C4 C5 116.1(5) . . ? O1A C4A C13A 112.1(4) . . ? O1A C4A C5A 102.1(5) . . ? C13A C4A C5A 117.3(5) . . ? O1A C4A C3A 101.2(4) . . ? C13A C4A C3A 116.9(5) . . ? C5A C4A C3A 105.1(5) . . ? O2 C5 C6 110.9(5) . . ? O2 C5 C4 113.4(5) . . ? C6 C5 C4 101.9(5) . . ? O2 C5 H5 110.1 . . ? C6 C5 H5 110.1 . . ? C4 C5 H5 110.1 . . ? O3A C5A C6A 127.9(6) . . ? O3A C5A C4A 127.5(5) . . ? C6A C5A C4A 104.5(5) . . ? O4 C6 C5 110.6(5) . . ? O4 C6 C1 110.6(5) . . ? C5 C6 C1 101.1(5) . . ? O4 C6 H6 111.4 . . ? C5 C6 H6 111.4 . . ? C1 C6 H6 111.4 . . ? C5A C6A C1A 100.4(5) . . ? C5A C6A H6A1 111.7 . . ? C1A C6A H6A1 111.7 . . ? C5A C6A H6A2 111.7 . . ? C1A C6A H6A2 111.7 . . ? H6A1 C6A H6A2 109.5 . . ? Si1 C7 H7A 109.5 . . ? Si1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? Si1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? Si1A C7A H7A1 109.5 . . ? Si1A C7A H7A2 109.5 . . ? H7A1 C7A H7A2 109.5 . . ? Si1A C7A H7A3 109.5 . . ? H7A1 C7A H7A3 109.5 . . ? H7A2 C7A H7A3 109.5 . . ? Si1 C8 H8A 109.5 . . ? Si1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? Si1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? Si1A C8A H8A1 109.5 . . ? Si1A C8A H8A2 109.5 . . ? H8A1 C8A H8A2 109.5 . . ? Si1A C8A H8A3 109.5 . . ? H8A1 C8A H8A3 109.5 . . ? H8A2 C8A H8A3 109.5 . . ? C12 C9 C10 109.0(6) . . ? C12 C9 C11 108.9(5) . . ? C10 C9 C11 108.8(6) . . ? C12 C9 Si1 111.3(5) . . ? C10 C9 Si1 110.1(4) . . ? C11 C9 Si1 108.6(4) . . ? C10A C9A C11A 109.3(6) . . ? C10A C9A C12A 108.3(5) . . ? C11A C9A C12A 108.5(6) . . ? C10A C9A Si1A 112.2(5) . . ? C11A C9A Si1A 109.6(4) . . ? C12A C9A Si1A 108.7(5) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9A C10A H10D 109.5 . . ? C9A C10A H10E 109.5 . . ? H10D C10A H10E 109.5 . . ? C9A C10A H10F 109.5 . . ? H10D C10A H10F 109.5 . . ? H10E C10A H10F 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9A C11A H11D 109.5 . . ? C9A C11A H11E 109.5 . . ? H11D C11A H11E 109.5 . . ? C9A C11A H11F 109.5 . . ? H11D C11A H11F 109.5 . . ? H11E C11A H11F 109.5 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C9A C12A H12D 109.5 . . ? C9A C12A H12E 109.5 . . ? H12D C12A H12E 109.5 . . ? C9A C12A H12F 109.5 . . ? H12D C12A H12F 109.5 . . ? H12E C12A H12F 109.5 . . ? C14 C13 C4 112.7(5) . . ? C14 C13 H13C 109.0 . . ? C4 C13 H13C 109.0 . . ? C14 C13 H13D 109.0 . . ? C4 C13 H13D 109.0 . . ? H13C C13 H13D 107.8 . . ? C14A C13A C4A 114.3(5) . . ? C14A C13A H13A 108.7 . . ? C4A C13A H13A 108.7 . . ? C14A C13A H13B 108.7 . . ? C4A C13A H13B 108.7 . . ? H13A C13A H13B 107.6 . . ? C15 C14 C13 124.8(7) . . ? C15 C14 H14 117.6 . . ? C13 C14 H14 117.6 . . ? C15A C14A C13A 124.9(7) . . ? C15A C14A H14A 117.6 . . ? C13A C14A H14A 117.6 . . ? C14 C15 H15C 120.0 . . ? C14 C15 H15D 120.0 . . ? H15C C15 H15D 120.0 . . ? C14A C15A H15A 120.0 . . ? C14A C15A H15B 120.0 . . ? H15A C15A H15B 120.0 . . ? C4 O1 C1 97.5(4) . . ? C4A O1A C1A 97.3(4) . . ? C5 O2 H2 109.5 . . ? C3A O2A H2A 109.5 . . ? C6 O4 Si1 126.0(4) . . ? C2A O4A Si1A 125.1(4) . . ? _diffrn_measured_fraction_theta_max 0.735 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.796 _refine_diff_density_max 0.418 _refine_diff_density_min -0.374 _refine_diff_density_rms 0.100 data_ohj192 _database_code_depnum_ccdc_archive 'CCDC 898467' #TrackingRef '13569_web_deposit_cif_file_2_JosephHarrity_1346140167.ohj192.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H11 Cl O3' _chemical_formula_weight 202.63 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' Cl Cl 0.1484 0.1585 '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 7.5774(18) _cell_length_b 7.5917(14) _cell_length_c 16.577(4) _cell_angle_alpha 77.041(13) _cell_angle_beta 88.566(19) _cell_angle_gamma 85.931(13) _cell_volume 926.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3107 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 27.23 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.452 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 0.382 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9414 _exptl_absorpt_correction_T_max 0.9556 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 20873 _diffrn_reflns_av_R_equivalents 0.1309 _diffrn_reflns_av_sigmaI/netI 0.1089 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.26 _diffrn_reflns_theta_max 28.02 _reflns_number_total 4045 _reflns_number_gt 2448 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1639P)^2^+11.7371P] 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 4045 _refine_ls_number_parameters 239 _refine_ls_number_restraints 146 _refine_ls_R_factor_all 0.1930 _refine_ls_R_factor_gt 0.1434 _refine_ls_wR_factor_ref 0.3872 _refine_ls_wR_factor_gt 0.3560 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.077 _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 Cl1 Cl 0.7281(3) 0.6266(3) 0.86508(16) 0.0326(6) Uani 1 1 d . . . Cl2 Cl 0.9406(3) -0.2932(3) 0.63338(16) 0.0329(6) Uani 1 1 d . . . O1 O 0.2561(8) 1.0313(7) 0.9697(4) 0.0216(13) Uani 1 1 d . . . H1 H 0.1521 1.0429 0.9838 0.032 Uiso 1 1 calc R . . O2 O 0.0367(8) 0.7538(8) 0.9907(4) 0.0261(14) Uani 1 1 d . . . O3 O 0.5731(8) 1.0065(7) 0.8819(4) 0.0253(14) Uani 1 1 d . . . H3 H 0.5944 1.0177 0.8323 0.038 Uiso 1 1 calc R . . O4 O 0.7485(9) 0.4582(7) 0.5097(4) 0.0270(14) Uani 1 1 d . . . O5 O 0.4816(8) 0.2301(7) 0.5309(4) 0.0229(13) Uani 1 1 d . . . H5 H 0.4928 0.3300 0.5005 0.034 Uiso 1 1 calc R . . O6 O 0.5514(9) -0.1298(7) 0.6201(4) 0.0268(14) Uani 1 1 d . . . H6 H 0.5198 -0.1756 0.5830 0.040 Uiso 1 1 calc R . . C1 C 0.5011(12) 0.7186(11) 0.8557(6) 0.0240(12) Uani 1 1 d U . . H1A H 0.4793 0.7812 0.7980 0.029 Uiso 1 1 calc R . . C2 C 0.4695(11) 0.8535(10) 0.9104(6) 0.0231(11) Uani 1 1 d U . . H2 H 0.5065 0.7940 0.9667 0.028 Uiso 1 1 calc R . . C3 C 0.2724(11) 0.9145(10) 0.9129(6) 0.0221(10) Uani 1 1 d U . . C4 C 0.2017(11) 1.0150(11) 0.8257(5) 0.0227(12) Uani 1 1 d U . . H4A H 0.2686 1.1206 0.8053 0.027 Uiso 1 1 calc R . . H4B H 0.2210 0.9353 0.7876 0.027 Uiso 1 1 calc R . . C5 C 0.0104(12) 1.0734(11) 0.8272(6) 0.0252(13) Uani 1 1 d U . . H5A H -0.0699 0.9838 0.8358 0.030 Uiso 1 1 calc R . . C6 C -0.0542(13) 1.2439(12) 0.8170(6) 0.0304(17) Uani 1 1 d U . . H6A H 0.0221 1.3372 0.8082 0.037 Uiso 1 1 calc R . . H6B H -0.1758 1.2702 0.8187 0.037 Uiso 1 1 calc R . . C7 C 0.1676(12) 0.7471(10) 0.9462(6) 0.0224(11) Uani 1 1 d U . . C8 C 0.2283(12) 0.5782(11) 0.9212(6) 0.0236(12) Uani 1 1 d U . . H8 H 0.1597 0.4787 0.9348 0.028 Uiso 1 1 calc R . . C9 C 0.3801(12) 0.5651(11) 0.8793(6) 0.0241(12) Uani 1 1 d U . . H9 H 0.4125 0.4566 0.8639 0.029 Uiso 1 1 calc R . . C10 C 0.9941(12) 0.0592(10) 0.6186(6) 0.0251(12) Uani 1 1 d U . . H10 H 1.1108 0.0192 0.6320 0.030 Uiso 1 1 calc R . . C11 C 0.9595(12) 0.2349(10) 0.5778(6) 0.0248(12) Uani 1 1 d U . . H11 H 1.0520 0.3109 0.5649 0.030 Uiso 1 1 calc R . . C12 C 0.7784(12) 0.3059(10) 0.5540(6) 0.0231(12) Uani 1 1 d U . . C13 C 0.6266(12) 0.1855(10) 0.5868(6) 0.0242(11) Uani 1 1 d U . . C14 C 0.5683(12) 0.2109(10) 0.6733(6) 0.0255(12) Uani 1 1 d U . . H14A H 0.4684 0.1384 0.6918 0.031 Uiso 1 1 calc R . . H14B H 0.6643 0.1656 0.7116 0.031 Uiso 1 1 calc R . . C15 C 0.5170(12) 0.4032(11) 0.6766(6) 0.0260(13) Uani 1 1 d U . . H15 H 0.6067 0.4807 0.6767 0.031 Uiso 1 1 calc R . . C16 C 0.3501(13) 0.4693(11) 0.6794(6) 0.0278(17) Uani 1 1 d U . . H16A H 0.2579 0.3947 0.6794 0.033 Uiso 1 1 calc R . . H16B H 0.3257 0.5900 0.6814 0.033 Uiso 1 1 calc R . . C17 C 0.8547(12) -0.0721(10) 0.6427(6) 0.0250(12) Uani 1 1 d U . . H17 H 0.8225 -0.0778 0.7008 0.030 Uiso 1 1 calc R . . C18 C 0.6884(12) -0.0151(10) 0.5906(6) 0.0245(12) Uani 1 1 d U . . H18 H 0.7179 -0.0268 0.5340 0.029 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 Cl1 0.0180(12) 0.0257(11) 0.0578(16) -0.0193(10) 0.0036(9) 0.0039(8) Cl2 0.0289(14) 0.0161(9) 0.0558(15) -0.0152(9) 0.0032(10) 0.0057(8) O1 0.013(3) 0.014(3) 0.043(4) -0.019(2) 0.002(2) 0.002(2) O2 0.014(3) 0.022(3) 0.045(4) -0.014(3) 0.006(3) 0.001(2) O3 0.017(3) 0.017(3) 0.045(4) -0.013(3) 0.007(3) -0.006(2) O4 0.027(4) 0.016(3) 0.040(4) -0.012(2) 0.002(3) 0.001(2) O5 0.022(3) 0.007(2) 0.043(4) -0.011(2) 0.000(3) 0.001(2) O6 0.025(4) 0.011(3) 0.048(4) -0.015(3) 0.001(3) -0.004(2) C1 0.016(3) 0.017(2) 0.043(3) -0.017(2) 0.005(2) -0.0007(19) C2 0.015(2) 0.015(2) 0.042(3) -0.015(2) 0.005(2) -0.0027(19) C3 0.015(2) 0.0161(19) 0.039(2) -0.0156(18) 0.0052(18) -0.0018(17) C4 0.016(2) 0.018(2) 0.038(3) -0.015(2) 0.005(2) 0.0005(19) C5 0.016(3) 0.024(3) 0.039(3) -0.014(2) 0.003(2) -0.001(2) C6 0.021(4) 0.027(3) 0.045(4) -0.014(3) 0.001(3) 0.004(3) C7 0.016(2) 0.016(2) 0.040(3) -0.0161(19) 0.005(2) -0.0028(18) C8 0.017(3) 0.015(2) 0.043(3) -0.016(2) 0.005(2) -0.0007(19) C9 0.017(3) 0.016(2) 0.043(3) -0.016(2) 0.005(2) 0.0002(19) C10 0.021(3) 0.014(2) 0.043(3) -0.012(2) 0.004(2) 0.0024(19) C11 0.021(3) 0.012(2) 0.043(3) -0.011(2) 0.005(2) 0.0019(19) C12 0.021(3) 0.010(2) 0.041(3) -0.014(2) 0.005(2) 0.0019(18) C13 0.022(2) 0.0107(19) 0.043(2) -0.0136(18) 0.004(2) 0.0014(17) C14 0.023(3) 0.014(2) 0.043(3) -0.013(2) 0.004(2) 0.002(2) C15 0.024(3) 0.015(2) 0.042(3) -0.014(2) 0.002(2) 0.002(2) C16 0.027(4) 0.017(3) 0.040(4) -0.012(3) 0.003(3) 0.008(3) C17 0.022(3) 0.013(2) 0.044(3) -0.015(2) 0.004(2) 0.0005(19) C18 0.022(3) 0.011(2) 0.046(3) -0.017(2) 0.004(2) -0.0003(19) _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 Cl1 C1 1.807(9) . ? Cl2 C17 1.795(8) . ? O1 C3 1.429(9) . ? O1 H1 0.8200 . ? O2 C7 1.226(10) . ? O3 C2 1.433(10) . ? O3 H3 0.8200 . ? O4 C12 1.232(10) . ? O5 C13 1.428(11) . ? O5 H5 0.8200 . ? O6 C18 1.410(10) . ? O6 H6 0.8200 . ? C1 C9 1.511(12) . ? C1 C2 1.516(10) . ? C1 H1A 0.9800 . ? C2 C3 1.535(12) . ? C2 H2 0.9800 . ? C3 C7 1.535(11) . ? C3 C4 1.564(13) . ? C4 C5 1.487(12) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.327(12) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C6 H6B 0.9300 . ? C7 C8 1.475(10) . ? C8 C9 1.338(12) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.364(11) . ? C10 C17 1.490(12) . ? C10 H10 0.9300 . ? C11 C12 1.468(13) . ? C11 H11 0.9300 . ? C12 C13 1.533(12) . ? C13 C14 1.539(12) . ? C13 C18 1.549(10) . ? C14 C15 1.496(10) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.331(12) . ? C15 H15 0.9300 . ? C16 H16A 0.9300 . ? C16 H16B 0.9300 . ? C17 C18 1.527(13) . ? C17 H17 0.9800 . ? C18 H18 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 C3 O1 H1 109.5 . . ? C2 O3 H3 109.5 . . ? C13 O5 H5 109.5 . . ? C18 O6 H6 109.5 . . ? C9 C1 C2 111.4(7) . . ? C9 C1 Cl1 109.0(6) . . ? C2 C1 Cl1 109.6(6) . . ? C9 C1 H1A 108.9 . . ? C2 C1 H1A 108.9 . . ? Cl1 C1 H1A 108.9 . . ? O3 C2 C1 110.4(7) . . ? O3 C2 C3 110.5(6) . . ? C1 C2 C3 110.7(7) . . ? O3 C2 H2 108.4 . . ? C1 C2 H2 108.4 . . ? C3 C2 H2 108.4 . . ? O1 C3 C2 106.1(7) . . ? O1 C3 C7 109.3(7) . . ? C2 C3 C7 108.7(7) . . ? O1 C3 C4 110.8(6) . . ? C2 C3 C4 112.1(7) . . ? C7 C3 C4 109.7(7) . . ? C5 C4 C3 112.7(7) . . ? C5 C4 H4A 109.1 . . ? C3 C4 H4A 109.1 . . ? C5 C4 H4B 109.1 . . ? C3 C4 H4B 109.1 . . ? H4A C4 H4B 107.8 . . ? C6 C5 C4 124.8(9) . . ? C6 C5 H5A 117.6 . . ? C4 C5 H5A 117.6 . . ? C5 C6 H6A 120.0 . . ? C5 C6 H6B 120.0 . . ? H6A C6 H6B 120.0 . . ? O2 C7 C8 121.1(7) . . ? O2 C7 C3 121.5(7) . . ? C8 C7 C3 117.4(7) . . ? C9 C8 C7 121.3(8) . . ? C9 C8 H8 119.3 . . ? C7 C8 H8 119.3 . . ? C8 C9 C1 122.9(7) . . ? C8 C9 H9 118.5 . . ? C1 C9 H9 118.5 . . ? C11 C10 C17 123.4(8) . . ? C11 C10 H10 118.3 . . ? C17 C10 H10 118.3 . . ? C10 C11 C12 121.0(8) . . ? C10 C11 H11 119.5 . . ? C12 C11 H11 119.5 . . ? O4 C12 C11 121.3(8) . . ? O4 C12 C13 120.8(8) . . ? C11 C12 C13 117.9(7) . . ? O5 C13 C12 109.7(7) . . ? O5 C13 C14 110.4(7) . . ? C12 C13 C14 110.0(7) . . ? O5 C13 C18 107.1(6) . . ? C12 C13 C18 109.4(7) . . ? C14 C13 C18 110.3(7) . . ? C15 C14 C13 114.0(7) . . ? C15 C14 H14A 108.7 . . ? C13 C14 H14A 108.7 . . ? C15 C14 H14B 108.7 . . ? C13 C14 H14B 108.7 . . ? H14A C14 H14B 107.6 . . ? C16 C15 C14 123.6(8) . . ? C16 C15 H15 118.2 . . ? C14 C15 H15 118.2 . . ? C15 C16 H16A 120.0 . . ? C15 C16 H16B 120.0 . . ? H16A C16 H16B 120.0 . . ? C10 C17 C18 112.0(8) . . ? C10 C17 Cl2 109.6(6) . . ? C18 C17 Cl2 110.1(6) . . ? C10 C17 H17 108.3 . . ? C18 C17 H17 108.3 . . ? Cl2 C17 H17 108.3 . . ? O6 C18 C17 111.2(7) . . ? O6 C18 C13 110.9(7) . . ? C17 C18 C13 111.4(7) . . ? O6 C18 H18 107.7 . . ? C17 C18 H18 107.7 . . ? C13 C18 H18 107.7 . . ? _diffrn_measured_fraction_theta_max 0.906 _diffrn_reflns_theta_full 28.02 _diffrn_measured_fraction_theta_full 0.906 _refine_diff_density_max 2.864 _refine_diff_density_min -0.684 _refine_diff_density_rms 0.188 data_ohj202_0m _database_code_depnum_ccdc_archive 'CCDC 898468' #TrackingRef '13570_web_deposit_cif_file_3_JosephHarrity_1346140167.ohj202_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H15 N O8 S' _chemical_formula_sum 'C15 H15 N O8 S' _chemical_formula_weight 369.34 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' N N 0.0061 0.0033 '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 Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.1742(3) _cell_length_b 12.7465(3) _cell_length_c 12.9261(3) _cell_angle_alpha 77.0340(10) _cell_angle_beta 65.9850(10) _cell_angle_gamma 82.4980(10) _cell_volume 1637.25(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6033 _cell_measurement_theta_min 2.18 _cell_measurement_theta_max 29.49 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.498 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.243 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9508 _exptl_absorpt_correction_T_max 0.9808 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 23767 _diffrn_reflns_av_R_equivalents 0.0276 _diffrn_reflns_av_sigmaI/netI 0.0429 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 31.35 _reflns_number_total 9297 _reflns_number_gt 6275 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0779P)^2^+0.1904P] 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 9297 _refine_ls_number_parameters 455 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0819 _refine_ls_R_factor_gt 0.0479 _refine_ls_wR_factor_ref 0.1436 _refine_ls_wR_factor_gt 0.1210 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 S1 S 0.24895(4) 0.18097(4) 0.34024(4) 0.02482(12) Uani 1 1 d . . . S2 S 0.21869(4) 0.28904(4) 0.69787(4) 0.02465(12) Uani 1 1 d . . . O1 O 0.21958(12) 0.16950(10) 0.68321(11) 0.0244(3) Uani 1 1 d . . . O2 O 0.19152(13) 0.29195(11) 0.81500(12) 0.0334(3) Uani 1 1 d . . . O3 O 0.13549(13) 0.34662(11) 0.64381(13) 0.0350(3) Uani 1 1 d . . . O4 O 0.85493(14) 0.39352(13) 0.43507(15) 0.0438(4) Uani 1 1 d . . . O5 O 0.79883(16) 0.44507(14) 0.28950(14) 0.0506(4) Uani 1 1 d . . . O6 O 0.29172(16) -0.24232(12) 0.86602(14) 0.0437(4) Uani 1 1 d . . . O7 O 0.14079(13) -0.11034(12) 1.01998(12) 0.0405(4) Uani 1 1 d . . . H7 H 0.1691 -0.1691 1.0485 0.061 Uiso 1 1 calc R . . O8 O 0.07422(12) -0.00135(12) 0.83866(13) 0.0338(3) Uani 1 1 d . . . H8 H 0.0025 0.0266 0.8783 0.051 Uiso 1 1 calc R . . O9 O 0.26240(11) 0.30023(10) 0.34706(11) 0.0234(3) Uani 1 1 d . . . O10 O 0.28362(13) 0.17223(12) 0.22375(12) 0.0368(3) Uani 1 1 d . . . O11 O 0.31859(13) 0.11851(11) 0.40517(12) 0.0339(3) Uani 1 1 d . . . O12 O -0.39492(14) 0.12131(12) 0.55340(14) 0.0413(4) Uani 1 1 d . . . O13 O -0.37001(16) 0.09788(14) 0.71366(15) 0.0519(4) Uani 1 1 d . . . O14 O 0.35125(13) 0.57688(12) 0.00530(11) 0.0355(3) Uani 1 1 d . . . H14 H 0.3256 0.6362 -0.0246 0.053 Uiso 1 1 calc R . . O15 O 0.21761(15) 0.71484(12) 0.15701(13) 0.0385(3) Uani 1 1 d . . . O16 O 0.41732(11) 0.46336(12) 0.18659(11) 0.0299(3) Uani 1 1 d . . . H16 H 0.4854 0.4648 0.1259 0.045 Uiso 1 1 calc R . . N1 N 0.77331(16) 0.40909(14) 0.39232(16) 0.0343(4) Uani 1 1 d . . . N2 N -0.32678(16) 0.11429(14) 0.60841(16) 0.0350(4) Uani 1 1 d . . . C1 C 0.28152(16) 0.08400(14) 0.74338(15) 0.0224(4) Uani 1 1 d . . . H1 H 0.3492 0.1153 0.7583 0.027 Uiso 1 1 calc R . . C2 C 0.17681(16) 0.03279(15) 0.85905(16) 0.0260(4) Uani 1 1 d . . . H2 H 0.1416 0.0861 0.9117 0.031 Uiso 1 1 calc R . . C3 C 0.24123(17) -0.06523(16) 0.91304(16) 0.0280(4) Uani 1 1 d . . . C4 C 0.29511(17) -0.14461(16) 0.83044(17) 0.0297(4) Uani 1 1 d . . . C5 C 0.35571(17) -0.09955(16) 0.70577(17) 0.0273(4) Uani 1 1 d . . . H5 H 0.4021 -0.1470 0.6538 0.033 Uiso 1 1 calc R . . C6 C 0.34740(16) 0.00508(15) 0.66399(16) 0.0241(4) Uani 1 1 d . . . H6 H 0.3835 0.0304 0.5830 0.029 Uiso 1 1 calc R . . C7 C 0.38336(17) 0.32615(14) 0.60913(16) 0.0236(4) Uani 1 1 d . . . C8 C 0.46431(18) 0.34640(15) 0.65895(17) 0.0277(4) Uani 1 1 d . . . H8A H 0.4331 0.3414 0.7400 0.033 Uiso 1 1 calc R . . C9 C 0.59331(19) 0.37444(15) 0.58737(18) 0.0297(4) Uani 1 1 d . . . H9 H 0.6514 0.3881 0.6193 0.036 Uiso 1 1 calc R . . C10 C 0.63510(17) 0.38206(15) 0.46922(17) 0.0272(4) Uani 1 1 d . . . C11 C 0.55482(19) 0.36495(15) 0.41798(17) 0.0299(4) Uani 1 1 d . . . H11 H 0.5853 0.3728 0.3366 0.036 Uiso 1 1 calc R . . C12 C 0.42668(18) 0.33556(15) 0.49005(16) 0.0282(4) Uani 1 1 d . . . H12 H 0.3689 0.3219 0.4577 0.034 Uiso 1 1 calc R . . C13 C 0.35891(18) -0.03671(17) 0.93363(17) 0.0319(4) Uani 1 1 d . . . H13A H 0.3895 -0.1016 0.9764 0.038 Uiso 1 1 calc R . . H13B H 0.4317 -0.0154 0.8582 0.038 Uiso 1 1 calc R . . C14 C 0.3260(2) 0.0536(2) 1.00069(18) 0.0397(5) Uani 1 1 d . . . H14A H 0.2576 0.0435 1.0754 0.048 Uiso 1 1 calc R . . C15 C 0.3855(3) 0.1447(2) 0.9627(2) 0.0472(6) Uani 1 1 d . . . H15A H 0.4544 0.1574 0.8883 0.057 Uiso 1 1 calc R . . H15B H 0.3599 0.1981 1.0094 0.057 Uiso 1 1 calc R . . C16 C 0.07840(16) 0.16029(14) 0.41987(15) 0.0229(4) Uani 1 1 d . . . C17 C 0.02310(19) 0.16197(16) 0.53802(17) 0.0297(4) Uani 1 1 d . . . H17 H 0.0763 0.1741 0.5754 0.036 Uiso 1 1 calc R . . C18 C -0.11091(19) 0.14573(16) 0.60100(17) 0.0312(4) Uani 1 1 d . . . H18 H -0.1505 0.1468 0.6812 0.037 Uiso 1 1 calc R . . C19 C -0.18331(18) 0.12804(15) 0.54233(17) 0.0279(4) Uani 1 1 d . . . C20 C -0.12967(18) 0.12491(16) 0.42593(18) 0.0315(4) Uani 1 1 d . . . H20 H -0.1831 0.1122 0.3890 0.038 Uiso 1 1 calc R . . C21 C 0.00493(18) 0.14078(16) 0.36288(17) 0.0288(4) Uani 1 1 d . . . H21 H 0.0444 0.1381 0.2830 0.035 Uiso 1 1 calc R . . C22 C 0.20476(16) 0.38930(14) 0.28557(15) 0.0223(4) Uani 1 1 d . . . H22 H 0.1323 0.3622 0.2735 0.027 Uiso 1 1 calc R . . C23 C 0.14905(15) 0.47091(15) 0.36291(15) 0.0231(4) Uani 1 1 d . . . H23 H 0.1133 0.4469 0.4442 0.028 Uiso 1 1 calc R . . C24 C 0.14871(16) 0.57512(15) 0.32030(16) 0.0250(4) Uani 1 1 d . . . H24 H 0.1098 0.6242 0.3717 0.030 Uiso 1 1 calc R . . C25 C 0.20736(16) 0.61778(15) 0.19450(16) 0.0258(4) Uani 1 1 d . . . C26 C 0.24986(16) 0.53650(15) 0.11345(15) 0.0254(4) Uani 1 1 d . . . C27 C 0.31014(16) 0.43578(15) 0.16766(15) 0.0235(4) Uani 1 1 d . . . H27 H 0.3395 0.3812 0.1164 0.028 Uiso 1 1 calc R . . C28 C 0.12504(18) 0.51520(16) 0.09846(16) 0.0294(4) Uani 1 1 d . . . H28A H 0.0530 0.4994 0.1755 0.035 Uiso 1 1 calc R . . H28B H 0.0985 0.5814 0.0545 0.035 Uiso 1 1 calc R . . C29 C 0.1432(2) 0.42304(19) 0.03696(18) 0.0379(5) Uani 1 1 d . . . H29 H 0.2132 0.4252 -0.0364 0.046 Uiso 1 1 calc R . . C30 C 0.0683(2) 0.3404(2) 0.0786(2) 0.0451(6) Uani 1 1 d . . . H30A H -0.0025 0.3359 0.1518 0.054 Uiso 1 1 calc R . . H30B H 0.0847 0.2848 0.0357 0.054 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 0.0235(2) 0.0230(3) 0.0281(2) -0.00774(19) -0.01036(18) 0.00442(17) S2 0.0251(2) 0.0209(2) 0.0292(2) -0.00540(19) -0.01265(18) 0.00307(17) O1 0.0267(6) 0.0211(7) 0.0286(7) -0.0024(5) -0.0157(5) 0.0005(5) O2 0.0376(7) 0.0328(8) 0.0296(7) -0.0102(6) -0.0113(6) 0.0009(6) O3 0.0307(7) 0.0296(8) 0.0460(9) -0.0033(6) -0.0207(6) 0.0072(6) O4 0.0316(7) 0.0379(9) 0.0607(11) -0.0061(8) -0.0182(7) -0.0031(6) O5 0.0464(9) 0.0578(12) 0.0382(9) -0.0054(8) -0.0046(7) -0.0174(8) O6 0.0543(9) 0.0245(9) 0.0475(10) 0.0034(7) -0.0209(8) 0.0001(7) O7 0.0284(7) 0.0381(9) 0.0334(8) 0.0088(6) -0.0005(6) 0.0058(6) O8 0.0190(6) 0.0351(8) 0.0436(9) -0.0039(7) -0.0103(6) -0.0015(5) O9 0.0255(6) 0.0217(7) 0.0256(7) -0.0022(5) -0.0140(5) -0.0005(5) O10 0.0364(7) 0.0423(9) 0.0311(8) -0.0168(7) -0.0086(6) 0.0021(6) O11 0.0298(7) 0.0275(8) 0.0433(8) -0.0020(6) -0.0176(6) 0.0060(6) O12 0.0305(7) 0.0295(8) 0.0647(11) -0.0089(7) -0.0197(7) -0.0005(6) O13 0.0420(9) 0.0578(12) 0.0431(10) -0.0056(8) -0.0022(7) -0.0135(8) O14 0.0297(7) 0.0370(9) 0.0224(7) 0.0053(6) -0.0010(5) 0.0072(6) O15 0.0479(8) 0.0254(8) 0.0353(8) 0.0023(6) -0.0135(7) -0.0017(6) O16 0.0173(6) 0.0399(8) 0.0273(7) -0.0026(6) -0.0060(5) 0.0008(5) N1 0.0334(9) 0.0238(9) 0.0420(11) -0.0053(8) -0.0102(8) -0.0058(7) N2 0.0307(8) 0.0206(9) 0.0463(11) -0.0047(8) -0.0078(8) -0.0031(7) C1 0.0207(7) 0.0213(9) 0.0255(9) -0.0015(7) -0.0112(7) 0.0003(7) C2 0.0205(8) 0.0258(10) 0.0290(10) -0.0032(8) -0.0090(7) 0.0019(7) C3 0.0221(8) 0.0293(11) 0.0244(9) -0.0001(8) -0.0050(7) 0.0039(7) C4 0.0244(8) 0.0278(11) 0.0356(11) -0.0026(9) -0.0129(8) 0.0015(7) C5 0.0233(8) 0.0262(10) 0.0306(10) -0.0067(8) -0.0085(7) 0.0006(7) C6 0.0176(7) 0.0269(10) 0.0261(9) -0.0045(8) -0.0071(7) -0.0012(7) C7 0.0264(8) 0.0160(9) 0.0294(10) -0.0023(7) -0.0134(7) 0.0007(7) C8 0.0327(9) 0.0245(10) 0.0301(10) -0.0051(8) -0.0168(8) -0.0005(7) C9 0.0321(9) 0.0243(10) 0.0381(11) -0.0054(9) -0.0191(8) -0.0025(8) C10 0.0270(8) 0.0159(9) 0.0358(11) -0.0027(8) -0.0101(8) -0.0023(7) C11 0.0367(10) 0.0242(10) 0.0274(10) -0.0015(8) -0.0123(8) -0.0031(8) C12 0.0350(10) 0.0241(10) 0.0303(10) -0.0027(8) -0.0185(8) -0.0028(8) C13 0.0300(9) 0.0390(12) 0.0263(10) -0.0058(9) -0.0133(8) 0.0074(8) C14 0.0405(11) 0.0545(15) 0.0271(11) -0.0152(10) -0.0158(9) 0.0092(10) C15 0.0599(14) 0.0546(16) 0.0370(13) -0.0216(12) -0.0264(11) 0.0115(12) C16 0.0260(8) 0.0159(9) 0.0271(9) -0.0037(7) -0.0116(7) 0.0012(7) C17 0.0332(9) 0.0291(11) 0.0304(10) -0.0059(8) -0.0158(8) -0.0014(8) C18 0.0366(10) 0.0250(11) 0.0291(10) -0.0040(8) -0.0104(8) -0.0011(8) C19 0.0264(8) 0.0157(9) 0.0368(11) -0.0015(8) -0.0091(8) -0.0020(7) C20 0.0314(9) 0.0293(11) 0.0392(12) -0.0071(9) -0.0183(9) -0.0036(8) C21 0.0331(9) 0.0274(11) 0.0290(10) -0.0081(8) -0.0138(8) -0.0013(8) C22 0.0223(8) 0.0228(10) 0.0225(9) -0.0024(7) -0.0115(7) 0.0029(7) C23 0.0176(7) 0.0288(10) 0.0204(9) -0.0047(7) -0.0054(6) 0.0005(7) C24 0.0199(7) 0.0283(10) 0.0259(9) -0.0079(8) -0.0082(7) 0.0034(7) C25 0.0210(8) 0.0243(11) 0.0283(10) -0.0007(8) -0.0086(7) 0.0007(7) C26 0.0221(8) 0.0266(10) 0.0204(9) 0.0001(7) -0.0053(7) 0.0048(7) C27 0.0206(7) 0.0270(10) 0.0206(9) -0.0042(7) -0.0077(7) 0.0047(7) C28 0.0303(9) 0.0344(11) 0.0252(10) -0.0079(8) -0.0145(8) 0.0091(8) C29 0.0377(11) 0.0524(15) 0.0285(11) -0.0159(10) -0.0169(9) 0.0096(10) C30 0.0558(14) 0.0473(15) 0.0441(13) -0.0202(12) -0.0289(11) 0.0095(11) _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 O11 1.4191(13) . ? S1 O10 1.4208(14) . ? S1 O9 1.5722(13) . ? S1 C16 1.7815(18) . ? S2 O3 1.4184(13) . ? S2 O2 1.4263(14) . ? S2 O1 1.5755(13) . ? S2 C7 1.7863(18) . ? O1 C1 1.460(2) . ? O4 N1 1.221(2) . ? O5 N1 1.229(2) . ? O6 C4 1.227(2) . ? O7 C3 1.432(2) . ? O7 H7 0.8400 . ? O8 C2 1.414(2) . ? O8 H8 0.8400 . ? O9 C22 1.468(2) . ? O12 N2 1.220(2) . ? O13 N2 1.221(2) . ? O14 C26 1.429(2) . ? O14 H14 0.8400 . ? O15 C25 1.225(2) . ? O16 C27 1.416(2) . ? O16 H16 0.8400 . ? N1 C10 1.493(2) . ? N2 C19 1.491(2) . ? C1 C6 1.504(2) . ? C1 C2 1.539(2) . ? C1 H1 1.0000 . ? C2 C3 1.533(2) . ? C2 H2 1.0000 . ? C3 C4 1.526(3) . ? C3 C13 1.545(3) . ? C4 C5 1.478(3) . ? C5 C6 1.328(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.382(2) . ? C7 C12 1.394(3) . ? C8 C9 1.401(3) . ? C8 H8A 0.9500 . ? C9 C10 1.387(3) . ? C9 H9 0.9500 . ? C10 C11 1.375(3) . ? C11 C12 1.399(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.513(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.308(3) . ? C14 H14A 0.9500 . ? C15 H15A 0.9500 . ? C15 H15B 0.9500 . ? C16 C21 1.381(2) . ? C16 C17 1.399(3) . ? C17 C18 1.400(3) . ? C17 H17 0.9500 . ? C18 C19 1.380(3) . ? C18 H18 0.9500 . ? C19 C20 1.382(3) . ? C20 C21 1.405(3) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 C23 1.503(2) . ? C22 C27 1.542(2) . ? C22 H22 1.0000 . ? C23 C24 1.319(3) . ? C23 H23 0.9500 . ? C24 C25 1.483(3) . ? C24 H24 0.9500 . ? C25 C26 1.533(3) . ? C26 C27 1.532(2) . ? C26 C28 1.549(3) . ? C27 H27 1.0000 . ? C28 C29 1.510(3) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 C30 1.307(3) . ? C29 H29 0.9500 . ? C30 H30A 0.9500 . ? C30 H30B 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 O11 S1 O10 120.44(8) . . ? O11 S1 O9 103.76(8) . . ? O10 S1 O9 109.97(8) . . ? O11 S1 C16 108.36(8) . . ? O10 S1 C16 109.65(8) . . ? O9 S1 C16 103.19(7) . . ? O3 S2 O2 120.45(8) . . ? O3 S2 O1 103.79(8) . . ? O2 S2 O1 110.19(8) . . ? O3 S2 C7 108.30(8) . . ? O2 S2 C7 109.75(8) . . ? O1 S2 C7 102.83(7) . . ? C1 O1 S2 118.88(11) . . ? C3 O7 H7 109.5 . . ? C2 O8 H8 109.5 . . ? C22 O9 S1 119.40(10) . . ? C26 O14 H14 109.5 . . ? C27 O16 H16 109.5 . . ? O4 N1 O5 123.65(18) . . ? O4 N1 C10 118.07(17) . . ? O5 N1 C10 118.28(17) . . ? O12 N2 O13 123.59(18) . . ? O12 N2 C19 117.54(17) . . ? O13 N2 C19 118.86(18) . . ? O1 C1 C6 106.71(14) . . ? O1 C1 C2 109.31(13) . . ? C6 C1 C2 112.85(15) . . ? O1 C1 H1 109.3 . . ? C6 C1 H1 109.3 . . ? C2 C1 H1 109.3 . . ? O8 C2 C3 109.30(16) . . ? O8 C2 C1 109.21(15) . . ? C3 C2 C1 108.05(14) . . ? O8 C2 H2 110.1 . . ? C3 C2 H2 110.1 . . ? C1 C2 H2 110.1 . . ? O7 C3 C4 111.94(17) . . ? O7 C3 C2 106.22(14) . . ? C4 C3 C2 108.92(15) . . ? O7 C3 C13 110.44(16) . . ? C4 C3 C13 106.24(14) . . ? C2 C3 C13 113.18(16) . . ? O6 C4 C5 121.01(19) . . ? O6 C4 C3 121.44(18) . . ? C5 C4 C3 117.52(17) . . ? C6 C5 C4 122.16(18) . . ? C6 C5 H5 118.9 . . ? C4 C5 H5 118.9 . . ? C5 C6 C1 120.82(17) . . ? C5 C6 H6 119.6 . . ? C1 C6 H6 119.6 . . ? C8 C7 C12 121.39(17) . . ? C8 C7 S2 119.82(14) . . ? C12 C7 S2 118.78(13) . . ? C7 C8 C9 118.59(18) . . ? C7 C8 H8A 120.7 . . ? C9 C8 H8A 120.7 . . ? C10 C9 C8 119.15(17) . . ? C10 C9 H9 120.4 . . ? C8 C9 H9 120.4 . . ? C11 C10 C9 123.00(17) . . ? C11 C10 N1 117.34(17) . . ? C9 C10 N1 119.66(16) . . ? C10 C11 C12 117.56(18) . . ? C10 C11 H11 121.2 . . ? C12 C11 H11 121.2 . . ? C7 C12 C11 120.28(17) . . ? C7 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C14 C13 C3 112.91(16) . . ? C14 C13 H13A 109.0 . . ? C3 C13 H13A 109.0 . . ? C14 C13 H13B 109.0 . . ? C3 C13 H13B 109.0 . . ? H13A C13 H13B 107.8 . . ? C15 C14 C13 124.4(2) . . ? C15 C14 H14A 117.8 . . ? C13 C14 H14A 117.8 . . ? C14 C15 H15A 120.0 . . ? C14 C15 H15B 120.0 . . ? H15A C15 H15B 120.0 . . ? C21 C16 C17 121.84(17) . . ? C21 C16 S1 118.55(14) . . ? C17 C16 S1 119.60(13) . . ? C16 C17 C18 119.81(17) . . ? C16 C17 H17 120.1 . . ? C18 C17 H17 120.1 . . ? C19 C18 C17 117.59(18) . . ? C19 C18 H18 121.2 . . ? C17 C18 H18 121.2 . . ? C18 C19 C20 123.21(17) . . ? C18 C19 N2 117.65(18) . . ? C20 C19 N2 119.12(17) . . ? C19 C20 C21 119.17(17) . . ? C19 C20 H20 120.4 . . ? C21 C20 H20 120.4 . . ? C16 C21 C20 118.36(18) . . ? C16 C21 H21 120.8 . . ? C20 C21 H21 120.8 . . ? O9 C22 C23 106.21(13) . . ? O9 C22 C27 110.02(13) . . ? C23 C22 C27 112.49(15) . . ? O9 C22 H22 109.4 . . ? C23 C22 H22 109.4 . . ? C27 C22 H22 109.4 . . ? C24 C23 C22 121.38(16) . . ? C24 C23 H23 119.3 . . ? C22 C23 H23 119.3 . . ? C23 C24 C25 121.86(17) . . ? C23 C24 H24 119.1 . . ? C25 C24 H24 119.1 . . ? O15 C25 C24 120.95(18) . . ? O15 C25 C26 121.41(17) . . ? C24 C25 C26 117.60(16) . . ? O14 C26 C27 105.86(13) . . ? O14 C26 C25 111.38(16) . . ? C27 C26 C25 108.16(14) . . ? O14 C26 C28 111.62(15) . . ? C27 C26 C28 113.72(16) . . ? C25 C26 C28 106.14(13) . . ? O16 C27 C26 110.23(15) . . ? O16 C27 C22 108.13(14) . . ? C26 C27 C22 108.01(13) . . ? O16 C27 H27 110.1 . . ? C26 C27 H27 110.1 . . ? C22 C27 H27 110.1 . . ? C29 C28 C26 113.50(15) . . ? C29 C28 H28A 108.9 . . ? C26 C28 H28A 108.9 . . ? C29 C28 H28B 108.9 . . ? C26 C28 H28B 108.9 . . ? H28A C28 H28B 107.7 . . ? C30 C29 C28 123.9(2) . . ? C30 C29 H29 118.0 . . ? C28 C29 H29 118.0 . . ? C29 C30 H30A 120.0 . . ? C29 C30 H30B 120.0 . . ? H30A C30 H30B 120.0 . . ? _diffrn_measured_fraction_theta_max 0.863 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.586 _refine_diff_density_min -0.425 _refine_diff_density_rms 0.093