# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2009 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'Krayushkin, Mikhail' 'Levchenko, Konstantin' 'Yarovenko, Vladimir' 'Christoforova, Ludmila' 'Barachevsky, Valery' 'Puankov, Yury' 'Valova, Tatyana' 'Kobeleva, Olga' 'Lyssenko, Konstantin' _publ_contact_author_name 'Levchenko, Konstantin' _publ_contact_author_email ? _publ_section_title ; Synthesis and reactivity of 1-aryl-9\/D-thieno[3,4-b]chromon-9-ones ; # Attachment '- 19a.cif' data_a _database_code_depnum_ccdc_archive 'CCDC 742366' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C42 H26 O5 S3, C7.5 H13' _chemical_formula_sum 'C49.50 H39 O5 S3' _chemical_formula_weight 809.99 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 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 12.116(2) _cell_length_b 12.633(3) _cell_length_c 14.075(3) _cell_angle_alpha 75.424(7) _cell_angle_beta 88.977(6) _cell_angle_gamma 73.821(7) _cell_volume 1999.2(8) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 806 _cell_measurement_theta_min 3 _cell_measurement_theta_max 27 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.350 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 853 _exptl_absorpt_coefficient_mu 0.235 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.933 _exptl_absorpt_correction_T_max 0.954 _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 area detector'" _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14629 _diffrn_reflns_av_R_equivalents 0.0284 _diffrn_reflns_av_sigmaI/netI 0.0604 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 27.50 _reflns_number_total 9103 _reflns_number_gt 6580 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX II' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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. Analysis of the Fourier density synthesis has revealed that 19a crystallizes with solvate molecule, which is the superposition of n-alkanes (crystals were obtained from the petroleum ether). Upon the refinement of the solvate molecule, its atoms C(7S), C(8s), C(9s) and C(10s) disordered around the center of symmetry were refined with occupancies equal to 0.5, 0.5, 0.25 and 0.25, respectively. Due to the complicated disordering scheme the hydrogens for C(8S)-C(10S) atoms were not adde. The C(8s)-C(10S) bond length was refined with the constraints on it bond lengths. ; _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^)+(0.0960P)^2^+0.7739P] 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 onstr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9103 _refine_ls_number_parameters 523 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0778 _refine_ls_R_factor_gt 0.0511 _refine_ls_wR_factor_ref 0.1531 _refine_ls_wR_factor_gt 0.1335 _refine_ls_goodness_of_fit_ref 0.926 _refine_ls_restrained_S_all 0.929 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.001 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 0.85481(14) 0.21171(14) 0.16856(12) 0.0172(3) Uani 1 1 d . . . C2 C 0.79344(19) 0.1537(2) 0.23387(16) 0.0150(5) Uani 1 1 d . . . C3 C 0.6980(2) 0.21258(19) 0.27158(16) 0.0152(5) Uani 1 1 d . . . S4 S 0.63699(5) 0.11667(5) 0.34704(4) 0.01772(14) Uani 1 1 d . . . C6 C 0.8207(2) 0.03192(19) 0.26719(17) 0.0155(5) Uani 1 1 d . . . C7 C 0.9293(2) -0.0373(2) 0.23764(17) 0.0181(5) Uani 1 1 d . . . C8 C 0.9857(2) 0.0293(2) 0.16088(17) 0.0183(5) Uani 1 1 d . . . C9 C 1.0818(2) -0.0281(2) 0.11704(19) 0.0223(5) Uani 1 1 d . . . H9A H 1.1101 -0.1088 0.1379 0.027 Uiso 1 1 calc R . . C10 C 1.1351(2) 0.0321(2) 0.0441(2) 0.0275(6) Uani 1 1 d . . . H10A H 1.2003 -0.0071 0.0154 0.033 Uiso 1 1 calc R . . C11 C 1.0930(2) 0.1505(2) 0.0127(2) 0.0257(6) Uani 1 1 d . . . H11A H 1.1296 0.1915 -0.0379 0.031 Uiso 1 1 calc R . . C12 C 0.9983(2) 0.2096(2) 0.05408(18) 0.0222(5) Uani 1 1 d . . . H12A H 0.9698 0.2902 0.0322 0.027 Uiso 1 1 calc R . . C13 C 0.9463(2) 0.1482(2) 0.12815(17) 0.0178(5) Uani 1 1 d . . . O14 O 0.97145(15) -0.14040(14) 0.27333(14) 0.0244(4) Uani 1 1 d . . . C15 C 0.7397(2) -0.0020(2) 0.32975(17) 0.0170(5) Uani 1 1 d . . . C16 C 0.7212(2) -0.1141(2) 0.37716(18) 0.0188(5) Uani 1 1 d . . . C17 C 0.6565(2) -0.1257(2) 0.46038(19) 0.0243(5) Uani 1 1 d . . . H17A H 0.6311 -0.0636 0.4897 0.029 Uiso 1 1 calc R . . C18 C 0.6286(2) -0.2273(2) 0.5011(2) 0.0281(6) Uani 1 1 d . . . H18A H 0.5830 -0.2333 0.5567 0.034 Uiso 1 1 calc R . . C19 C 0.6676(2) -0.3191(2) 0.4603(2) 0.0272(6) Uani 1 1 d . . . H19A H 0.6482 -0.3880 0.4876 0.033 Uiso 1 1 calc R . . C20 C 0.7350(2) -0.3105(2) 0.3795(2) 0.0271(6) Uani 1 1 d . . . H20A H 0.7641 -0.3744 0.3531 0.033 Uiso 1 1 calc R . . C21 C 0.7601(2) -0.2084(2) 0.33702(19) 0.0225(5) Uani 1 1 d . . . H21A H 0.8041 -0.2024 0.2803 0.027 Uiso 1 1 calc R . . C22 C 0.64599(19) 0.34002(19) 0.25308(16) 0.0139(4) Uani 1 1 d . . . H22A H 0.6970 0.3790 0.2098 0.017 Uiso 1 1 calc R . . C23 C 0.52755(19) 0.37833(19) 0.20167(16) 0.0138(4) Uani 1 1 d . . . C24 C 0.50528(19) 0.37257(19) 0.10825(16) 0.0135(4) Uani 1 1 d . . . O25 O 0.59388(13) 0.32889(14) 0.05436(11) 0.0155(3) Uani 1 1 d . . . C26 C 0.5656(2) 0.31752(19) -0.03600(16) 0.0150(5) Uani 1 1 d . . . C27 C 0.6557(2) 0.2609(2) -0.08366(17) 0.0180(5) Uani 1 1 d . . . H27A H 0.7319 0.2338 -0.0546 0.022 Uiso 1 1 calc R . . C28 C 0.6329(2) 0.2446(2) -0.17373(18) 0.0219(5) Uani 1 1 d . . . H28A H 0.6940 0.2051 -0.2062 0.026 Uiso 1 1 calc R . . C29 C 0.5213(2) 0.2852(2) -0.21833(18) 0.0232(5) Uani 1 1 d . . . H29A H 0.5068 0.2732 -0.2803 0.028 Uiso 1 1 calc R . . C30 C 0.4330(2) 0.3427(2) -0.17112(18) 0.0210(5) Uani 1 1 d . . . H30A H 0.3574 0.3712 -0.2013 0.025 Uiso 1 1 calc R . . C31 C 0.4534(2) 0.3596(2) -0.07879(17) 0.0160(5) Uani 1 1 d . . . C32 C 0.3567(2) 0.4215(2) -0.02837(17) 0.0163(5) Uani 1 1 d . . . C33 C 0.38735(19) 0.41563(19) 0.07295(17) 0.0142(4) Uani 1 1 d . . . C34 C 0.3183(2) 0.4535(2) 0.14456(16) 0.0155(5) Uani 1 1 d . . . S35 S 0.39880(5) 0.43423(5) 0.24985(4) 0.01541(14) Uani 1 1 d . . . O36 O 0.26128(14) 0.47185(16) -0.07069(12) 0.0222(4) Uani 1 1 d . . . C37 C 0.19251(19) 0.4981(2) 0.14755(16) 0.0153(5) Uani 1 1 d . . . C38 C 0.1171(2) 0.4488(2) 0.11202(17) 0.0178(5) Uani 1 1 d . . . H38A H 0.1465 0.3890 0.0807 0.021 Uiso 1 1 calc R . . C39 C -0.0004(2) 0.4869(2) 0.12232(18) 0.0193(5) Uani 1 1 d . . . H39A H -0.0510 0.4530 0.0981 0.023 Uiso 1 1 calc R . . C40 C -0.0447(2) 0.5746(2) 0.16804(17) 0.0197(5) Uani 1 1 d . . . H40A H -0.1253 0.6004 0.1746 0.024 Uiso 1 1 calc R . . C41 C 0.0283(2) 0.6239(2) 0.20372(18) 0.0197(5) Uani 1 1 d . . . H41A H -0.0019 0.6836 0.2350 0.024 Uiso 1 1 calc R . . C42 C 0.1466(2) 0.5860(2) 0.19374(17) 0.0179(5) Uani 1 1 d . . . H42A H 0.1967 0.6200 0.2185 0.022 Uiso 1 1 calc R . . C43 C 0.6453(2) 0.36909(19) 0.35359(16) 0.0152(5) Uani 1 1 d . . . O44 O 0.55549(15) 0.38638(16) 0.39593(12) 0.0242(4) Uani 1 1 d . . . C45 C 0.7549(2) 0.36658(19) 0.39764(17) 0.0160(5) Uani 1 1 d . . . C46 C 0.8607(2) 0.3642(2) 0.34908(17) 0.0182(5) Uani 1 1 d . . . H46A H 0.8682 0.3645 0.2817 0.022 Uiso 1 1 calc R . . C47 C 0.9490(2) 0.3613(2) 0.40871(18) 0.0202(5) Uani 1 1 d . . . S48 S 0.90397(6) 0.36007(6) 0.52626(4) 0.02437(16) Uani 1 1 d . . . C49 C 0.7666(2) 0.3648(2) 0.49608(17) 0.0195(5) Uani 1 1 d . . . C50 C 0.6802(2) 0.3599(3) 0.57409(18) 0.0278(6) Uani 1 1 d . . . H50A H 0.6493 0.2955 0.5766 0.042 Uiso 1 1 calc R . . H50B H 0.6174 0.4310 0.5584 0.042 Uiso 1 1 calc R . . H50C H 0.7178 0.3501 0.6381 0.042 Uiso 1 1 calc R . . C51 C 1.0711(2) 0.3586(2) 0.3865(2) 0.0270(6) Uani 1 1 d . . . H51A H 1.0854 0.3483 0.3202 0.041 Uiso 1 1 calc R . . H51B H 1.1234 0.2951 0.4345 0.041 Uiso 1 1 calc R . . H51C H 1.0843 0.4305 0.3902 0.041 Uiso 1 1 calc R . . C1S C 1.0539(4) -0.0311(3) 0.4778(3) 0.0605(12) Uani 1 1 d . . . H1SA H 1.1127 -0.0775 0.5311 0.073 Uiso 1 1 calc R . . H1SB H 1.0338 -0.0832 0.4434 0.073 Uiso 1 1 calc R . . C2S C 1.1018(4) 0.0505(3) 0.4079(3) 0.0647(12) Uani 1 1 d . . . H2SA H 1.1206 0.1028 0.4427 0.078 Uiso 1 1 calc R . . H2SB H 1.0422 0.0968 0.3552 0.078 Uiso 1 1 calc R . . C3S C 1.2102(4) -0.0062(4) 0.3608(3) 0.0673(12) Uani 1 1 d . . . H3SA H 1.1922 -0.0595 0.3267 0.081 Uiso 1 1 calc R . . H3SB H 1.2709 -0.0510 0.4131 0.081 Uiso 1 1 calc R . . C4S C 1.2563(5) 0.0821(4) 0.2864(3) 0.0747(14) Uani 1 1 d . . . H4SA H 1.1959 0.1261 0.2337 0.090 Uiso 1 1 calc R . . H4SB H 1.2730 0.1361 0.3203 0.090 Uiso 1 1 calc R . . C5S C 1.3608(5) 0.0290(4) 0.2422(4) 0.0793(15) Uani 1 1 d . A . H5SA H 1.3436 -0.0265 0.2102 0.095 Uiso 1 1 calc R . . H5SB H 1.4206 -0.0144 0.2955 0.095 Uiso 1 1 calc R . . C6S C 1.4120(7) 0.1126(5) 0.1644(5) 0.137(3) Uani 1 1 d . . . H6SA H 1.4342 0.1624 0.1970 0.164 Uiso 1 1 d R A . H6SB H 1.3515 0.1587 0.1159 0.164 Uiso 1 1 d R . . C7S C 1.5086(8) 0.0607(7) 0.1154(6) 0.0480(18) Uiso 0.50 1 d P A 1 H7SA H 1.5581 -0.0051 0.1603 0.058 Uiso 0.50 1 d PR A 1 H7SB H 1.5521 0.1134 0.0893 0.058 Uiso 0.50 1 d PR A 1 C8S C 1.4582(7) 0.0288(8) 0.0346(7) 0.064(2) Uiso 0.50 1 d PD . . C9S C 1.4530(16) 0.0399(16) -0.0436(14) 0.067(5) Uiso 0.25 1 d P . 2 C10S C 1.5637(11) 0.0243(13) 0.1070(9) 0.043(3) Uiso 0.25 1 d PD . 2 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 0.0170(8) 0.0138(8) 0.0193(8) -0.0040(7) 0.0060(7) -0.0025(7) C2 0.0127(11) 0.0163(12) 0.0157(11) -0.0045(9) 0.0004(9) -0.0033(9) C3 0.0141(11) 0.0139(11) 0.0158(11) -0.0035(9) -0.0004(9) -0.0014(9) S4 0.0158(3) 0.0148(3) 0.0206(3) -0.0035(2) 0.0039(2) -0.0023(2) C6 0.0145(11) 0.0136(11) 0.0172(11) -0.0045(9) -0.0014(9) -0.0014(9) C7 0.0179(12) 0.0164(12) 0.0199(11) -0.0064(9) -0.0010(9) -0.0032(9) C8 0.0170(12) 0.0167(12) 0.0202(11) -0.0057(9) -0.0005(9) -0.0022(9) C9 0.0193(13) 0.0177(13) 0.0273(13) -0.0077(10) 0.0030(10) 0.0007(10) C10 0.0218(13) 0.0268(14) 0.0314(14) -0.0108(12) 0.0096(11) -0.0004(11) C11 0.0222(13) 0.0271(14) 0.0253(13) -0.0045(11) 0.0073(11) -0.0051(11) C12 0.0217(13) 0.0200(13) 0.0225(12) -0.0050(10) 0.0030(10) -0.0027(10) C13 0.0148(11) 0.0179(12) 0.0197(11) -0.0074(9) 0.0016(9) -0.0008(9) O14 0.0231(10) 0.0142(9) 0.0321(10) -0.0053(7) 0.0032(8) 0.0000(7) C15 0.0164(12) 0.0150(12) 0.0177(11) -0.0043(9) 0.0006(9) -0.0014(9) C16 0.0168(12) 0.0145(12) 0.0223(12) -0.0014(9) -0.0002(9) -0.0030(9) C17 0.0221(13) 0.0187(13) 0.0282(13) -0.0038(10) 0.0046(11) -0.0019(10) C18 0.0215(13) 0.0231(14) 0.0344(15) 0.0005(11) 0.0068(11) -0.0055(11) C19 0.0219(13) 0.0189(13) 0.0382(15) 0.0007(11) -0.0011(11) -0.0085(11) C20 0.0303(15) 0.0192(13) 0.0331(14) -0.0077(11) -0.0029(12) -0.0080(11) C21 0.0226(13) 0.0210(13) 0.0245(12) -0.0058(10) 0.0019(10) -0.0073(10) C22 0.0131(11) 0.0121(11) 0.0152(10) -0.0042(9) 0.0014(8) -0.0008(9) C23 0.0124(11) 0.0124(11) 0.0158(10) -0.0035(8) 0.0017(8) -0.0024(9) C24 0.0126(11) 0.0109(11) 0.0158(10) -0.0035(9) 0.0023(8) -0.0017(8) O25 0.0108(8) 0.0194(9) 0.0154(8) -0.0066(6) 0.0016(6) -0.0008(6) C26 0.0173(11) 0.0134(11) 0.0153(10) -0.0044(9) 0.0035(9) -0.0058(9) C27 0.0148(11) 0.0194(12) 0.0197(11) -0.0055(9) 0.0029(9) -0.0043(9) C28 0.0210(13) 0.0260(14) 0.0198(12) -0.0084(10) 0.0086(10) -0.0066(11) C29 0.0232(13) 0.0318(15) 0.0185(12) -0.0103(11) 0.0036(10) -0.0104(11) C30 0.0156(12) 0.0283(14) 0.0213(12) -0.0083(10) -0.0002(10) -0.0081(10) C31 0.0148(11) 0.0181(12) 0.0165(11) -0.0053(9) 0.0040(9) -0.0062(9) C32 0.0145(11) 0.0167(12) 0.0180(11) -0.0038(9) 0.0019(9) -0.0056(9) C33 0.0123(11) 0.0133(11) 0.0170(11) -0.0044(9) 0.0019(9) -0.0033(9) C34 0.0148(11) 0.0153(11) 0.0158(11) -0.0042(9) 0.0001(9) -0.0029(9) S35 0.0122(3) 0.0174(3) 0.0152(3) -0.0057(2) 0.0014(2) -0.0005(2) O36 0.0133(8) 0.0319(10) 0.0197(8) -0.0060(7) 0.0003(7) -0.0040(7) C37 0.0138(11) 0.0161(12) 0.0142(10) -0.0022(9) 0.0027(8) -0.0028(9) C38 0.0155(11) 0.0189(12) 0.0185(11) -0.0068(9) 0.0039(9) -0.0027(9) C39 0.0154(12) 0.0247(13) 0.0195(11) -0.0077(10) 0.0013(9) -0.0068(10) C40 0.0139(11) 0.0239(13) 0.0189(11) -0.0053(10) 0.0030(9) -0.0020(10) C41 0.0175(12) 0.0180(12) 0.0230(12) -0.0083(10) 0.0063(10) -0.0014(10) C42 0.0160(12) 0.0185(12) 0.0206(11) -0.0072(10) 0.0015(9) -0.0050(10) C43 0.0181(12) 0.0120(11) 0.0130(10) -0.0013(8) 0.0012(9) -0.0021(9) O44 0.0183(9) 0.0350(11) 0.0181(8) -0.0096(8) 0.0034(7) -0.0033(8) C45 0.0188(12) 0.0117(11) 0.0163(11) -0.0031(9) -0.0006(9) -0.0030(9) C46 0.0190(12) 0.0175(12) 0.0170(11) -0.0049(9) 0.0009(9) -0.0032(10) C47 0.0218(13) 0.0147(12) 0.0214(12) -0.0020(9) -0.0026(10) -0.0031(10) S48 0.0279(4) 0.0287(4) 0.0178(3) -0.0050(3) -0.0049(2) -0.0106(3) C49 0.0229(13) 0.0191(12) 0.0169(11) -0.0048(9) -0.0003(10) -0.0066(10) C50 0.0349(15) 0.0357(16) 0.0163(12) -0.0086(11) 0.0049(11) -0.0142(13) C51 0.0214(13) 0.0289(15) 0.0295(14) -0.0046(11) -0.0054(11) -0.0075(11) C1S 0.085(3) 0.040(2) 0.053(2) -0.0174(17) -0.035(2) -0.003(2) C2S 0.090(3) 0.035(2) 0.065(3) -0.0180(19) -0.035(2) -0.006(2) C3S 0.088(3) 0.053(2) 0.057(2) -0.011(2) -0.034(2) -0.014(2) C4S 0.098(4) 0.051(3) 0.069(3) -0.012(2) -0.036(3) -0.014(3) C5S 0.102(4) 0.046(3) 0.087(3) -0.006(2) -0.028(3) -0.025(3) C6S 0.214(8) 0.076(4) 0.123(5) 0.051(3) -0.108(5) -0.107(5) _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 C2 1.369(3) . ? O1 C13 1.381(3) . ? C2 C3 1.367(3) . ? C2 C6 1.434(3) . ? C3 C22 1.512(3) . ? C3 S4 1.722(2) . ? S4 C15 1.729(2) . ? C6 C15 1.390(3) . ? C6 C7 1.481(3) . ? C7 O14 1.233(3) . ? C7 C8 1.475(3) . ? C8 C13 1.399(3) . ? C8 C9 1.411(3) . ? C9 C10 1.380(4) . ? C9 H9A 0.9500 . ? C10 C11 1.394(4) . ? C10 H10A 0.9500 . ? C11 C12 1.389(3) . ? C11 H11A 0.9500 . ? C12 C13 1.388(4) . ? C12 H12A 0.9500 . ? C15 C16 1.483(3) . ? C16 C17 1.397(4) . ? C16 C21 1.406(3) . ? C17 C18 1.398(4) . ? C17 H17A 0.9500 . ? C18 C19 1.385(4) . ? C18 H18A 0.9500 . ? C19 C20 1.387(4) . ? C19 H19A 0.9500 . ? C20 C21 1.392(4) . ? C20 H20A 0.9500 . ? C21 H21A 0.9500 . ? C22 C23 1.514(3) . ? C22 C43 1.548(3) . ? C22 H22A 1.0000 . ? C23 C24 1.371(3) . ? C23 S35 1.727(2) . ? C24 O25 1.372(3) . ? C24 C33 1.429(3) . ? O25 C26 1.375(3) . ? C26 C27 1.391(3) . ? C26 C31 1.400(3) . ? C27 C28 1.379(3) . ? C27 H27A 0.9500 . ? C28 C29 1.403(4) . ? C28 H28A 0.9500 . ? C29 C30 1.378(3) . ? C29 H29A 0.9500 . ? C30 C31 1.406(3) . ? C30 H30A 0.9500 . ? C31 C32 1.492(3) . ? C32 O36 1.233(3) . ? C32 C33 1.459(3) . ? C33 C34 1.391(3) . ? C34 C37 1.474(3) . ? C34 S35 1.716(2) . ? C37 C38 1.401(3) . ? C37 C42 1.404(3) . ? C38 C39 1.387(3) . ? C38 H38A 0.9500 . ? C39 C40 1.395(3) . ? C39 H39A 0.9500 . ? C40 C41 1.380(3) . ? C40 H40A 0.9500 . ? C41 C42 1.397(3) . ? C41 H41A 0.9500 . ? C42 H42A 0.9500 . ? C43 O44 1.223(3) . ? C43 C45 1.464(3) . ? C45 C49 1.389(3) . ? C45 C46 1.439(3) . ? C46 C47 1.358(3) . ? C46 H46A 0.9500 . ? C47 C51 1.499(4) . ? C47 S48 1.730(3) . ? S48 C49 1.706(3) . ? C49 C50 1.505(3) . ? C50 H50A 0.9800 . ? C50 H50B 0.9800 . ? C50 H50C 0.9800 . ? C51 H51A 0.9800 . ? C51 H51B 0.9800 . ? C51 H51C 0.9800 . ? C1S C2S 1.472(6) . ? C1S C1S 1.536(8) 2_756 ? C1S H1SA 0.9900 . ? C1S H1SB 0.9900 . ? C2S C3S 1.537(6) . ? C2S H2SA 0.9900 . ? C2S H2SB 0.9900 . ? C3S C4S 1.545(7) . ? C3S H3SA 0.9900 . ? C3S H3SB 0.9900 . ? C4S C5S 1.467(7) . ? C4S H4SA 0.9900 . ? C4S H4SB 0.9900 . ? C5S C6S 1.567(7) . ? C5S H5SA 0.9900 . ? C5S H5SB 0.9900 . ? C6S C7S 1.431(10) . ? C6S H6SA 0.9601 . ? C6S H6SB 0.9599 . ? C7S C8S 1.489(11) . ? C7S H7SA 0.9599 . ? C7S H7SB 0.9600 . ? C8S C9S 1.076(18) . ? C8S C9S 1.164(18) 2_855 ? C8S C8S 1.555(18) 2_855 ? C8S C10S 1.628(9) . ? C9S C8S 1.164(18) 2_855 ? C9S C10S 1.40(2) 2_855 ? C9S C9S 1.61(4) 2_855 ? C10S C9S 1.40(2) 2_855 ? C10S H7SA 0.7595 . ? C10S H7SB 1.0575 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 C13 117.54(18) . . ? C3 C2 O1 119.9(2) . . ? C3 C2 C6 115.3(2) . . ? O1 C2 C6 124.8(2) . . ? C2 C3 C22 129.1(2) . . ? C2 C3 S4 108.90(17) . . ? C22 C3 S4 121.97(17) . . ? C3 S4 C15 94.35(11) . . ? C15 C6 C2 111.6(2) . . ? C15 C6 C7 130.0(2) . . ? C2 C6 C7 118.3(2) . . ? O14 C7 C8 121.9(2) . . ? O14 C7 C6 124.5(2) . . ? C8 C7 C6 113.6(2) . . ? C13 C8 C9 118.1(2) . . ? C13 C8 C7 122.4(2) . . ? C9 C8 C7 119.5(2) . . ? C10 C9 C8 120.6(2) . . ? C10 C9 H9A 119.7 . . ? C8 C9 H9A 119.7 . . ? C9 C10 C11 119.7(2) . . ? C9 C10 H10A 120.1 . . ? C11 C10 H10A 120.1 . . ? C12 C11 C10 121.1(2) . . ? C12 C11 H11A 119.4 . . ? C10 C11 H11A 119.4 . . ? C11 C12 C13 118.6(2) . . ? C11 C12 H12A 120.7 . . ? C13 C12 H12A 120.7 . . ? O1 C13 C12 116.0(2) . . ? O1 C13 C8 122.2(2) . . ? C12 C13 C8 121.8(2) . . ? C6 C15 C16 133.8(2) . . ? C6 C15 S4 109.81(18) . . ? C16 C15 S4 116.28(17) . . ? C17 C16 C21 118.2(2) . . ? C17 C16 C15 119.7(2) . . ? C21 C16 C15 121.9(2) . . ? C18 C17 C16 120.9(2) . . ? C18 C17 H17A 119.6 . . ? C16 C17 H17A 119.6 . . ? C19 C18 C17 120.0(3) . . ? C19 C18 H18A 120.0 . . ? C17 C18 H18A 120.0 . . ? C20 C19 C18 120.0(2) . . ? C20 C19 H19A 120.0 . . ? C18 C19 H19A 120.0 . . ? C19 C20 C21 120.2(2) . . ? C19 C20 H20A 119.9 . . ? C21 C20 H20A 119.9 . . ? C20 C21 C16 120.7(2) . . ? C20 C21 H21A 119.7 . . ? C16 C21 H21A 119.7 . . ? C23 C22 C3 111.35(19) . . ? C23 C22 C43 112.91(18) . . ? C3 C22 C43 107.22(18) . . ? C23 C22 H22A 108.4 . . ? C3 C22 H22A 108.4 . . ? C43 C22 H22A 108.4 . . ? C24 C23 C22 124.9(2) . . ? C24 C23 S35 108.64(17) . . ? C22 C23 S35 126.48(16) . . ? C23 C24 O25 120.1(2) . . ? C23 C24 C33 115.8(2) . . ? O25 C24 C33 124.12(19) . . ? C24 O25 C26 117.47(17) . . ? O25 C26 C27 116.0(2) . . ? O25 C26 C31 122.9(2) . . ? C27 C26 C31 121.1(2) . . ? C28 C27 C26 119.0(2) . . ? C28 C27 H27A 120.5 . . ? C26 C27 H27A 120.5 . . ? C27 C28 C29 121.3(2) . . ? C27 C28 H28A 119.3 . . ? C29 C28 H28A 119.3 . . ? C30 C29 C28 119.2(2) . . ? C30 C29 H29A 120.4 . . ? C28 C29 H29A 120.4 . . ? C29 C30 C31 120.8(2) . . ? C29 C30 H30A 119.6 . . ? C31 C30 H30A 119.6 . . ? C26 C31 C30 118.6(2) . . ? C26 C31 C32 121.3(2) . . ? C30 C31 C32 120.2(2) . . ? O36 C32 C33 125.0(2) . . ? O36 C32 C31 121.6(2) . . ? C33 C32 C31 113.4(2) . . ? C34 C33 C24 110.6(2) . . ? C34 C33 C32 129.7(2) . . ? C24 C33 C32 119.6(2) . . ? C33 C34 C37 132.0(2) . . ? C33 C34 S35 111.12(17) . . ? C37 C34 S35 116.71(17) . . ? C34 S35 C23 93.84(11) . . ? C38 C37 C42 118.6(2) . . ? C38 C37 C34 121.4(2) . . ? C42 C37 C34 119.7(2) . . ? C39 C38 C37 120.3(2) . . ? C39 C38 H38A 119.9 . . ? C37 C38 H38A 119.9 . . ? C38 C39 C40 120.4(2) . . ? C38 C39 H39A 119.8 . . ? C40 C39 H39A 119.8 . . ? C41 C40 C39 120.1(2) . . ? C41 C40 H40A 119.9 . . ? C39 C40 H40A 119.9 . . ? C40 C41 C42 119.8(2) . . ? C40 C41 H41A 120.1 . . ? C42 C41 H41A 120.1 . . ? C41 C42 C37 120.8(2) . . ? C41 C42 H42A 119.6 . . ? C37 C42 H42A 119.6 . . ? O44 C43 C45 122.4(2) . . ? O44 C43 C22 119.3(2) . . ? C45 C43 C22 118.14(19) . . ? C49 C45 C46 112.0(2) . . ? C49 C45 C43 121.4(2) . . ? C46 C45 C43 126.6(2) . . ? C47 C46 C45 113.6(2) . . ? C47 C46 H46A 123.2 . . ? C45 C46 H46A 123.2 . . ? C46 C47 C51 129.9(2) . . ? C46 C47 S48 110.20(19) . . ? C51 C47 S48 119.88(18) . . ? C49 S48 C47 93.58(12) . . ? C45 C49 C50 129.4(2) . . ? C45 C49 S48 110.58(18) . . ? C50 C49 S48 119.93(18) . . ? C49 C50 H50A 109.5 . . ? C49 C50 H50B 109.5 . . ? H50A C50 H50B 109.5 . . ? C49 C50 H50C 109.5 . . ? H50A C50 H50C 109.5 . . ? H50B C50 H50C 109.5 . . ? C47 C51 H51A 109.5 . . ? C47 C51 H51B 109.5 . . ? H51A C51 H51B 109.5 . . ? C47 C51 H51C 109.5 . . ? H51A C51 H51C 109.5 . . ? H51B C51 H51C 109.5 . . ? C2S C1S C1S 111.1(4) . 2_756 ? C2S C1S H1SA 109.4 . . ? C1S C1S H1SA 109.4 2_756 . ? C2S C1S H1SB 109.4 . . ? C1S C1S H1SB 109.4 2_756 . ? H1SA C1S H1SB 108.0 . . ? C1S C2S C3S 113.8(3) . . ? C1S C2S H2SA 108.8 . . ? C3S C2S H2SA 108.8 . . ? C1S C2S H2SB 108.8 . . ? C3S C2S H2SB 108.8 . . ? H2SA C2S H2SB 107.7 . . ? C2S C3S C4S 112.2(4) . . ? C2S C3S H3SA 109.2 . . ? C4S C3S H3SA 109.2 . . ? C2S C3S H3SB 109.2 . . ? C4S C3S H3SB 109.2 . . ? H3SA C3S H3SB 107.9 . . ? C5S C4S C3S 112.6(4) . . ? C5S C4S H4SA 109.1 . . ? C3S C4S H4SA 109.1 . . ? C5S C4S H4SB 109.1 . . ? C3S C4S H4SB 109.1 . . ? H4SA C4S H4SB 107.8 . . ? C4S C5S C6S 115.9(5) . . ? C4S C5S H5SA 108.3 . . ? C6S C5S H5SA 108.3 . . ? C4S C5S H5SB 108.3 . . ? C6S C5S H5SB 108.3 . . ? H5SA C5S H5SB 107.4 . . ? C7S C6S C5S 116.1(6) . . ? C7S C6S H6SA 108.5 . . ? C5S C6S H6SA 108.0 . . ? C7S C6S H6SB 108.6 . . ? C5S C6S H6SB 107.7 . . ? H6SA C6S H6SB 107.6 . . ? C6S C7S C8S 105.1(7) . . ? C6S C7S H7SA 110.3 . . ? C8S C7S H7SA 111.4 . . ? C6S C7S H7SB 110.7 . . ? C8S C7S H7SB 110.7 . . ? H7SA C7S H7SB 108.7 . . ? C9S C8S C9S 92.2(17) . 2_855 ? C9S C8S C7S 144.4(13) . . ? C9S C8S C7S 83.0(11) 2_855 . ? C7S C8S C8S 118.1(9) . 2_855 ? C9S C8S C10S 130.3(14) . . ? C8S C8S C10S 92.5(9) 2_855 . ? C8S C9S C8S 87.8(17) . 2_855 ? C8S C9S C10S 136.2(19) . 2_855 ? C8S C9S C10S 78.3(12) 2_855 2_855 ? C10S C9S C9S 109.6(18) 2_855 2_855 ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.683 _refine_diff_density_min -0.495 _publ_section_references ; Bruker, Programs APEX II, version 2.0-1; SAINT, version 7.23A; SADABS, version 2004/1; XPREP, version 2005/2; SHELXTL, version 6.1. Bruker AXS Inc., Madison, WI, USA, 2005. G.M. Sheldrick, Programs SHELXS97 (crystal structure solution) and SHELXL97 (crystal structure refinement), University of Gottingen, Germany, 1997. ;