# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_k94e _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 2-mercapto-1,3-di(ethoxycarbonyl)azulene _chemical_melting_point ? _chemical_formula_moiety 'C16 H16 O4 S' _chemical_formula_sum 'C16 H16 O4 S' _chemical_formula_weight 304.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.8453(14) _cell_length_b 12.1730(15) _cell_length_c 12.2364(15) _cell_angle_alpha 109.364(2) _cell_angle_beta 106.530(3) _cell_angle_gamma 98.626(2) _cell_volume 1406.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2370 _cell_measurement_theta_min 2.76 _cell_measurement_theta_max 28.64 _exptl_crystal_description 'Square plate' _exptl_crystal_colour Red-orange _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.437 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.243 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.912 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'SADABS (2000)' _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 SMART APEX CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 12191 _diffrn_reflns_av_R_equivalents 0.0395 _diffrn_reflns_av_sigmaI/netI 0.0587 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.76 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5491 _reflns_number_gt 3772 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections except those that were flagged by the user for being in the beamstop. 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^)+(0.0794P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5491 _refine_ls_number_parameters 391 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0811 _refine_ls_R_factor_gt 0.0516 _refine_ls_wR_factor_ref 0.1346 _refine_ls_wR_factor_gt 0.1235 _refine_ls_goodness_of_fit_ref 0.960 _refine_ls_restrained_S_all 0.960 _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 0.22237(7) 0.34730(6) 0.86718(6) 0.02488(18) Uani 1 1 d . . . H1S H 0.143(3) 0.272(2) 0.877(2) 0.035(8) Uiso 1 1 d . . . O1 O 0.57255(16) 0.12209(15) 0.32731(16) 0.0229(4) Uani 1 1 d . . . O2 O 0.22996(16) -0.24974(14) 0.27256(15) 0.0220(4) Uani 1 1 d . . . O3 O 0.59476(17) 0.29458(15) 0.48352(16) 0.0265(4) Uani 1 1 d . . . O4 O 0.11261(17) -0.21375(15) 0.39882(16) 0.0248(4) Uani 1 1 d . . . C1 C 0.4329(2) 0.1145(2) 0.4390(2) 0.0190(5) Uani 1 1 d . . . C2 C 0.3725(2) -0.0091(2) 0.3676(2) 0.0188(5) Uani 1 1 d . . . H2 H 0.3941 -0.0573 0.3006 0.023 Uiso 1 1 calc R . . C3 C 0.2756(2) -0.0507(2) 0.4097(2) 0.0190(5) Uani 1 1 d . . . C4 C 0.1873(2) 0.0445(2) 0.5765(2) 0.0203(5) Uani 1 1 d . . . H4 H 0.1260 -0.0321 0.5491 0.024 Uiso 1 1 calc R . . C5 C 0.1776(2) 0.1338(2) 0.6752(2) 0.0223(6) Uani 1 1 d . . . H5 H 0.1097 0.1107 0.7043 0.027 Uiso 1 1 calc R . . C6 C 0.2547(2) 0.2549(2) 0.7389(2) 0.0195(5) Uani 1 1 d . . . C7 C 0.3566(2) 0.3146(2) 0.7123(2) 0.0217(6) Uani 1 1 d . . . H7 H 0.3961 0.3976 0.7653 0.026 Uiso 1 1 calc R . . C8 C 0.4072(2) 0.2699(2) 0.6206(2) 0.0196(5) Uani 1 1 d . . . H8 H 0.4758 0.3273 0.6191 0.024 Uiso 1 1 calc R . . C9 C 0.2716(2) 0.0472(2) 0.5100(2) 0.0173(5) Uani 1 1 d . . . C10 C 0.3740(2) 0.1536(2) 0.5294(2) 0.0176(5) Uani 1 1 d . . . C11 C 0.5398(2) 0.1876(2) 0.4213(2) 0.0201(5) Uani 1 1 d . . . C12 C 0.6786(2) 0.1855(2) 0.3022(2) 0.0246(6) Uani 1 1 d . . . H12A H 0.7633 0.2153 0.3743 0.030 Uiso 1 1 calc R . . H12B H 0.6557 0.2554 0.2855 0.030 Uiso 1 1 calc R . . C13 C 0.6930(3) 0.0963(2) 0.1902(2) 0.0293(6) Uani 1 1 d . . . H13A H 0.7628 0.1362 0.1691 0.044 Uiso 1 1 calc R . . H13B H 0.6081 0.0663 0.1201 0.044 Uiso 1 1 calc R . . H13C H 0.7176 0.0284 0.2086 0.044 Uiso 1 1 calc R . . C14 C 0.1968(2) -0.1761(2) 0.3625(2) 0.0185(5) Uani 1 1 d . . . C15 C 0.1679(3) -0.3776(2) 0.2330(2) 0.0238(6) Uani 1 1 d . . . H15A H 0.0696 -0.3952 0.1961 0.029 Uiso 1 1 calc R . . H15B H 0.1899 -0.4013 0.3047 0.029 Uiso 1 1 calc R . . C16 C 0.2213(3) -0.4459(2) 0.1388(2) 0.0279(6) Uani 1 1 d . . . H16A H 0.1826 -0.5329 0.1109 0.042 Uiso 1 1 calc R . . H16B H 0.3187 -0.4267 0.1761 0.042 Uiso 1 1 calc R . . H16C H 0.1975 -0.4227 0.0677 0.042 Uiso 1 1 calc R . . S2 S 0.12645(7) 0.47418(6) 0.62308(6) 0.02575(19) Uani 1 1 d . . . H2S H 0.031(3) 0.400(3) 0.622(2) 0.034(8) Uiso 1 1 d . . . O21 O 0.44709(16) 0.23496(15) 0.06290(16) 0.0223(4) Uani 1 1 d . . . O22 O 0.10650(16) -0.13153(14) 0.02042(15) 0.0207(4) Uani 1 1 d . . . O23 O 0.47103(17) 0.41063(15) 0.21557(17) 0.0292(4) Uani 1 1 d . . . O24 O -0.00179(17) -0.09265(15) 0.15425(16) 0.0245(4) Uani 1 1 d . . . C21 C 0.3164(2) 0.2306(2) 0.1833(2) 0.0196(5) Uani 1 1 d . . . C22 C 0.2538(2) 0.1069(2) 0.1134(2) 0.0200(5) Uani 1 1 d . . . H22 H 0.2717 0.0575 0.0444 0.024 Uiso 1 1 calc R . . C23 C 0.1614(2) 0.0677(2) 0.1610(2) 0.0174(5) Uani 1 1 d . . . C24 C 0.0831(2) 0.1653(2) 0.3344(2) 0.0199(5) Uani 1 1 d . . . H24 H 0.0231 0.0889 0.3102 0.024 Uiso 1 1 calc R . . C25 C 0.0773(2) 0.2572(2) 0.4352(2) 0.0208(5) Uani 1 1 d . . . H25 H 0.0142 0.2350 0.4696 0.025 Uiso 1 1 calc R . . C26 C 0.1527(2) 0.3789(2) 0.4931(2) 0.0213(5) Uani 1 1 d . . . C27 C 0.2513(3) 0.4356(2) 0.4618(2) 0.0237(6) Uani 1 1 d . . . H27 H 0.2916 0.5189 0.5132 0.028 Uiso 1 1 calc R . . C28 C 0.2991(2) 0.3898(2) 0.3685(2) 0.0212(6) Uani 1 1 d . . . H28 H 0.3670 0.4462 0.3648 0.025 Uiso 1 1 calc R . . C29 C 0.1627(2) 0.1670(2) 0.2629(2) 0.0179(5) Uani 1 1 d . . . C30 C 0.2626(2) 0.2720(2) 0.2777(2) 0.0179(5) Uani 1 1 d . . . C31 C 0.4173(2) 0.3029(2) 0.1585(2) 0.0215(6) Uani 1 1 d . . . C32 C 0.5430(3) 0.2979(2) 0.0276(3) 0.0267(6) Uani 1 1 d . . . H32A H 0.6286 0.3387 0.0985 0.032 Uiso 1 1 calc R . . H32B H 0.5090 0.3597 0.0014 0.032 Uiso 1 1 calc R . . C33 C 0.5630(3) 0.2048(2) -0.0785(2) 0.0269(6) Uani 1 1 d . . . H33A H 0.6253 0.2449 -0.1067 0.040 Uiso 1 1 calc R . . H33B H 0.4770 0.1632 -0.1470 0.040 Uiso 1 1 calc R . . H33C H 0.5996 0.1458 -0.0506 0.040 Uiso 1 1 calc R . . C34 C 0.0803(2) -0.0568(2) 0.1144(2) 0.0183(5) Uani 1 1 d . . . C35 C 0.0285(2) -0.2563(2) -0.0311(2) 0.0206(5) Uani 1 1 d . . . H35A H -0.0679 -0.2616 -0.0617 0.025 Uiso 1 1 calc R . . H35B H 0.0461 -0.2901 0.0332 0.025 Uiso 1 1 calc R . . C36 C 0.0680(3) -0.3257(2) -0.1359(2) 0.0251(6) Uani 1 1 d . . . H36A H 0.0184 -0.4111 -0.1708 0.038 Uiso 1 1 calc R . . H36B H 0.1640 -0.3181 -0.1050 0.038 Uiso 1 1 calc R . . H36C H 0.0474 -0.2933 -0.2003 0.038 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 0.0288(4) 0.0163(3) 0.0250(4) 0.0018(3) 0.0134(3) 0.0011(3) O1 0.0228(9) 0.0186(9) 0.0278(10) 0.0074(8) 0.0146(8) 0.0001(7) O2 0.0274(10) 0.0088(9) 0.0250(10) 0.0009(7) 0.0132(8) -0.0025(7) O3 0.0256(10) 0.0164(10) 0.0313(10) 0.0051(8) 0.0115(8) -0.0044(8) O4 0.0251(10) 0.0182(9) 0.0289(10) 0.0058(8) 0.0145(8) -0.0016(7) C1 0.0181(12) 0.0151(13) 0.0216(13) 0.0064(11) 0.0063(10) 0.0012(10) C2 0.0195(13) 0.0160(13) 0.0187(12) 0.0051(10) 0.0073(10) 0.0020(10) C3 0.0183(12) 0.0142(13) 0.0214(13) 0.0050(11) 0.0063(10) 0.0020(10) C4 0.0212(13) 0.0127(12) 0.0222(13) 0.0044(10) 0.0063(10) -0.0002(10) C5 0.0225(13) 0.0167(13) 0.0256(14) 0.0065(11) 0.0103(11) 0.0001(10) C6 0.0198(13) 0.0149(13) 0.0230(13) 0.0060(11) 0.0090(11) 0.0030(10) C7 0.0209(13) 0.0135(13) 0.0231(13) 0.0030(11) 0.0042(11) -0.0001(10) C8 0.0196(13) 0.0124(12) 0.0216(13) 0.0037(10) 0.0064(10) -0.0018(10) C9 0.0154(12) 0.0132(12) 0.0204(12) 0.0050(10) 0.0057(10) 0.0008(10) C10 0.0157(12) 0.0133(12) 0.0221(13) 0.0061(10) 0.0069(10) 0.0005(10) C11 0.0178(13) 0.0188(13) 0.0213(13) 0.0077(11) 0.0057(10) 0.0010(10) C12 0.0195(13) 0.0215(14) 0.0334(15) 0.0121(12) 0.0122(11) -0.0012(11) C13 0.0329(15) 0.0271(15) 0.0334(16) 0.0132(13) 0.0195(13) 0.0059(12) C14 0.0204(13) 0.0132(12) 0.0184(13) 0.0021(10) 0.0068(10) 0.0044(10) C15 0.0296(14) 0.0076(12) 0.0275(14) 0.0009(11) 0.0122(12) -0.0036(10) C16 0.0329(15) 0.0147(13) 0.0299(15) 0.0023(11) 0.0134(12) -0.0002(11) S2 0.0321(4) 0.0177(3) 0.0243(4) 0.0025(3) 0.0138(3) 0.0042(3) O21 0.0225(9) 0.0160(9) 0.0279(10) 0.0051(8) 0.0150(8) 0.0002(7) O22 0.0220(9) 0.0110(9) 0.0236(9) 0.0010(7) 0.0109(7) -0.0026(7) O23 0.0307(10) 0.0158(10) 0.0362(11) 0.0048(8) 0.0164(9) -0.0032(8) O24 0.0273(10) 0.0151(9) 0.0261(10) 0.0027(8) 0.0143(8) -0.0047(7) C21 0.0182(12) 0.0139(12) 0.0222(13) 0.0050(10) 0.0054(10) 0.0004(10) C22 0.0220(13) 0.0164(13) 0.0201(13) 0.0046(10) 0.0092(10) 0.0039(10) C23 0.0140(12) 0.0143(12) 0.0188(12) 0.0035(10) 0.0042(10) -0.0001(9) C24 0.0179(12) 0.0136(12) 0.0237(13) 0.0055(11) 0.0058(10) -0.0007(10) C25 0.0203(13) 0.0171(13) 0.0230(13) 0.0060(11) 0.0086(11) 0.0020(10) C26 0.0259(13) 0.0181(13) 0.0182(13) 0.0042(10) 0.0086(11) 0.0066(11) C27 0.0281(14) 0.0114(12) 0.0236(13) 0.0028(11) 0.0065(11) -0.0021(11) C28 0.0225(13) 0.0131(12) 0.0253(14) 0.0040(11) 0.0117(11) -0.0006(10) C29 0.0177(12) 0.0143(12) 0.0188(12) 0.0050(10) 0.0056(10) 0.0015(10) C30 0.0166(12) 0.0129(12) 0.0212(13) 0.0057(10) 0.0060(10) -0.0002(9) C31 0.0204(13) 0.0178(13) 0.0247(13) 0.0076(11) 0.0078(11) 0.0027(11) C32 0.0231(14) 0.0228(14) 0.0334(15) 0.0093(12) 0.0149(12) -0.0014(11) C33 0.0262(14) 0.0241(14) 0.0307(15) 0.0106(12) 0.0136(12) 0.0016(12) C34 0.0193(13) 0.0159(12) 0.0167(12) 0.0039(10) 0.0062(10) 0.0024(10) C35 0.0196(13) 0.0107(12) 0.0249(13) 0.0010(10) 0.0092(11) -0.0033(10) C36 0.0272(14) 0.0139(13) 0.0289(14) 0.0043(11) 0.0104(12) -0.0001(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 C6 1.765(3) . ? S1 H1S 1.23(3) . ? O1 C11 1.340(3) . ? O1 C12 1.451(3) . ? O2 C14 1.346(3) . ? O2 C15 1.453(3) . ? O3 C11 1.217(3) . ? O4 C14 1.217(3) . ? C1 C2 1.401(3) . ? C1 C10 1.415(3) . ? C1 C11 1.464(3) . ? C2 C3 1.396(3) . ? C2 H2 0.9500 . ? C3 C9 1.416(3) . ? C3 C14 1.462(3) . ? C4 C5 1.375(3) . ? C4 C9 1.390(3) . ? C4 H4 0.9500 . ? C5 C6 1.405(3) . ? C5 H5 0.9500 . ? C6 C7 1.406(3) . ? C7 C8 1.376(3) . ? C7 H7 0.9500 . ? C8 C10 1.397(3) . ? C8 H8 0.9500 . ? C9 C10 1.477(3) . ? C12 C13 1.506(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C15 C16 1.498(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? S2 C26 1.758(2) . ? S2 H2S 1.26(3) . ? O21 C31 1.346(3) . ? O21 C32 1.446(3) . ? O22 C34 1.342(3) . ? O22 C35 1.447(3) . ? O23 C31 1.216(3) . ? O24 C34 1.221(3) . ? C21 C22 1.403(3) . ? C21 C30 1.420(3) . ? C21 C31 1.463(3) . ? C22 C23 1.394(3) . ? C22 H22 0.9500 . ? C23 C29 1.415(3) . ? C23 C34 1.462(3) . ? C24 C25 1.388(3) . ? C24 C29 1.396(3) . ? C24 H24 0.9500 . ? C25 C26 1.406(3) . ? C25 H25 0.9500 . ? C26 C27 1.397(3) . ? C27 C28 1.374(3) . ? C27 H27 0.9500 . ? C28 C30 1.403(3) . ? C28 H28 0.9500 . ? C29 C30 1.469(3) . ? C32 C33 1.508(3) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C35 C36 1.498(3) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 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 C6 S1 H1S 100.4(13) . . ? C11 O1 C12 116.37(19) . . ? C14 O2 C15 114.37(18) . . ? C2 C1 C10 108.3(2) . . ? C2 C1 C11 124.5(2) . . ? C10 C1 C11 127.1(2) . . ? C3 C2 C1 109.7(2) . . ? C3 C2 H2 125.2 . . ? C1 C2 H2 125.2 . . ? C2 C3 C9 108.8(2) . . ? C2 C3 C14 125.5(2) . . ? C9 C3 C14 125.7(2) . . ? C5 C4 C9 130.8(2) . . ? C5 C4 H4 114.6 . . ? C9 C4 H4 114.6 . . ? C4 C5 C6 128.7(2) . . ? C4 C5 H5 115.6 . . ? C6 C5 H5 115.6 . . ? C5 C6 C7 127.8(2) . . ? C5 C6 S1 118.18(19) . . ? C7 C6 S1 114.06(18) . . ? C8 C7 C6 129.2(2) . . ? C8 C7 H7 115.4 . . ? C6 C7 H7 115.4 . . ? C7 C8 C10 130.3(2) . . ? C7 C8 H8 114.8 . . ? C10 C8 H8 114.8 . . ? C4 C9 C3 126.9(2) . . ? C4 C9 C10 126.7(2) . . ? C3 C9 C10 106.4(2) . . ? C8 C10 C1 126.7(2) . . ? C8 C10 C9 126.4(2) . . ? C1 C10 C9 106.9(2) . . ? O3 C11 O1 122.9(2) . . ? O3 C11 C1 125.4(2) . . ? O1 C11 C1 111.7(2) . . ? O1 C12 C13 106.9(2) . . ? O1 C12 H12A 110.3 . . ? C13 C12 H12A 110.3 . . ? O1 C12 H12B 110.3 . . ? C13 C12 H12B 110.3 . . ? H12A C12 H12B 108.6 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O4 C14 O2 122.1(2) . . ? O4 C14 C3 126.2(2) . . ? O2 C14 C3 111.7(2) . . ? O2 C15 C16 107.2(2) . . ? O2 C15 H15A 110.3 . . ? C16 C15 H15A 110.3 . . ? O2 C15 H15B 110.3 . . ? C16 C15 H15B 110.3 . . ? H15A C15 H15B 108.5 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C26 S2 H2S 98.3(12) . . ? C31 O21 C32 116.38(19) . . ? C34 O22 C35 115.01(18) . . ? C22 C21 C30 108.5(2) . . ? C22 C21 C31 124.6(2) . . ? C30 C21 C31 126.9(2) . . ? C23 C22 C21 109.4(2) . . ? C23 C22 H22 125.3 . . ? C21 C22 H22 125.3 . . ? C22 C23 C29 108.8(2) . . ? C22 C23 C34 125.0(2) . . ? C29 C23 C34 126.2(2) . . ? C25 C24 C29 130.5(2) . . ? C25 C24 H24 114.8 . . ? C29 C24 H24 114.8 . . ? C24 C25 C26 128.5(2) . . ? C24 C25 H25 115.8 . . ? C26 C25 H25 115.8 . . ? C27 C26 C25 127.8(2) . . ? C27 C26 S2 114.03(19) . . ? C25 C26 S2 118.17(19) . . ? C28 C27 C26 130.1(2) . . ? C28 C27 H27 114.9 . . ? C26 C27 H27 114.9 . . ? C27 C28 C30 129.6(2) . . ? C27 C28 H28 115.2 . . ? C30 C28 H28 115.2 . . ? C24 C29 C23 126.4(2) . . ? C24 C29 C30 126.8(2) . . ? C23 C29 C30 106.8(2) . . ? C28 C30 C21 126.7(2) . . ? C28 C30 C29 126.8(2) . . ? C21 C30 C29 106.6(2) . . ? O23 C31 O21 122.3(2) . . ? O23 C31 C21 126.1(2) . . ? O21 C31 C21 111.6(2) . . ? O21 C32 C33 107.3(2) . . ? O21 C32 H32A 110.3 . . ? C33 C32 H32A 110.3 . . ? O21 C32 H32B 110.3 . . ? C33 C32 H32B 110.3 . . ? H32A C32 H32B 108.5 . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? O24 C34 O22 122.0(2) . . ? O24 C34 C23 125.9(2) . . ? O22 C34 C23 112.0(2) . . ? O22 C35 C36 107.92(19) . . ? O22 C35 H35A 110.1 . . ? C36 C35 H35A 110.1 . . ? O22 C35 H35B 110.1 . . ? C36 C35 H35B 110.1 . . ? H35A C35 H35B 108.4 . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 C1 C2 C3 0.1(3) . . . . ? C11 C1 C2 C3 179.4(2) . . . . ? C1 C2 C3 C9 0.4(3) . . . . ? C1 C2 C3 C14 -176.5(2) . . . . ? C9 C4 C5 C6 -1.6(5) . . . . ? C4 C5 C6 C7 3.2(4) . . . . ? C4 C5 C6 S1 -177.5(2) . . . . ? C5 C6 C7 C8 -1.3(4) . . . . ? S1 C6 C7 C8 179.4(2) . . . . ? C6 C7 C8 C10 -0.9(5) . . . . ? C5 C4 C9 C3 179.1(2) . . . . ? C5 C4 C9 C10 -1.6(4) . . . . ? C2 C3 C9 C4 178.8(2) . . . . ? C14 C3 C9 C4 -4.4(4) . . . . ? C2 C3 C9 C10 -0.7(3) . . . . ? C14 C3 C9 C10 176.2(2) . . . . ? C7 C8 C10 C1 -179.0(2) . . . . ? C7 C8 C10 C9 0.1(4) . . . . ? C2 C1 C10 C8 178.7(2) . . . . ? C11 C1 C10 C8 -0.5(4) . . . . ? C2 C1 C10 C9 -0.5(3) . . . . ? C11 C1 C10 C9 -179.8(2) . . . . ? C4 C9 C10 C8 2.0(4) . . . . ? C3 C9 C10 C8 -178.5(2) . . . . ? C4 C9 C10 C1 -178.7(2) . . . . ? C3 C9 C10 C1 0.8(3) . . . . ? C12 O1 C11 O3 0.0(3) . . . . ? C12 O1 C11 C1 -179.46(19) . . . . ? C2 C1 C11 O3 -178.9(2) . . . . ? C10 C1 C11 O3 0.3(4) . . . . ? C2 C1 C11 O1 0.6(3) . . . . ? C10 C1 C11 O1 179.7(2) . . . . ? C11 O1 C12 C13 -177.3(2) . . . . ? C15 O2 C14 O4 -6.2(3) . . . . ? C15 O2 C14 C3 172.33(19) . . . . ? C2 C3 C14 O4 179.5(2) . . . . ? C9 C3 C14 O4 3.1(4) . . . . ? C2 C3 C14 O2 1.0(3) . . . . ? C9 C3 C14 O2 -175.4(2) . . . . ? C14 O2 C15 C16 -176.9(2) . . . . ? C30 C21 C22 C23 -0.2(3) . . . . ? C31 C21 C22 C23 -178.8(2) . . . . ? C21 C22 C23 C29 0.4(3) . . . . ? C21 C22 C23 C34 -178.0(2) . . . . ? C29 C24 C25 C26 -0.3(5) . . . . ? C24 C25 C26 C27 0.2(4) . . . . ? C24 C25 C26 S2 -178.2(2) . . . . ? C25 C26 C27 C28 0.6(5) . . . . ? S2 C26 C27 C28 179.0(2) . . . . ? C26 C27 C28 C30 -0.3(5) . . . . ? C25 C24 C29 C23 179.9(2) . . . . ? C25 C24 C29 C30 -0.8(4) . . . . ? C22 C23 C29 C24 179.0(2) . . . . ? C34 C23 C29 C24 -2.7(4) . . . . ? C22 C23 C29 C30 -0.4(3) . . . . ? C34 C23 C29 C30 177.9(2) . . . . ? C27 C28 C30 C21 179.9(3) . . . . ? C27 C28 C30 C29 -1.0(4) . . . . ? C22 C21 C30 C28 179.2(2) . . . . ? C31 C21 C30 C28 -2.3(4) . . . . ? C22 C21 C30 C29 0.0(3) . . . . ? C31 C21 C30 C29 178.5(2) . . . . ? C24 C29 C30 C28 1.6(4) . . . . ? C23 C29 C30 C28 -179.0(2) . . . . ? C24 C29 C30 C21 -179.2(2) . . . . ? C23 C29 C30 C21 0.2(3) . . . . ? C32 O21 C31 O23 -2.5(3) . . . . ? C32 O21 C31 C21 178.1(2) . . . . ? C22 C21 C31 O23 178.2(2) . . . . ? C30 C21 C31 O23 -0.1(4) . . . . ? C22 C21 C31 O21 -2.4(3) . . . . ? C30 C21 C31 O21 179.2(2) . . . . ? C31 O21 C32 C33 178.9(2) . . . . ? C35 O22 C34 O24 1.2(3) . . . . ? C35 O22 C34 C23 -179.39(19) . . . . ? C22 C23 C34 O24 -179.4(2) . . . . ? C29 C23 C34 O24 2.5(4) . . . . ? C22 C23 C34 O22 1.2(3) . . . . ? C29 C23 C34 O22 -176.8(2) . . . . ? C34 O22 C35 C36 178.72(19) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A S1 H1S O24 1.23(3) 2.31(3) 3.5043(18) 163.1(19) 2_556 S2 H2S O4 1.26(3) 2.44(3) 3.6632(18) 162.4(18) 2_556 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.655 _refine_diff_density_min -0.313 _refine_diff_density_rms 0.077 _database_code_depnum_ccdc_archive 'CCDC 941157' ####################################################################### # # 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_11037 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 2,6-dichloro-1,3-diethoxycarbonylazulene _chemical_melting_point 162 _chemical_formula_moiety 'C16 H14 Cl2 O4' _chemical_formula_sum 'C16 H14 Cl2 O4' _chemical_formula_weight 341.17 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 3.9099(11) _cell_length_b 13.413(4) _cell_length_c 14.207(4) _cell_angle_alpha 82.606(5) _cell_angle_beta 86.888(6) _cell_angle_gamma 82.453(6) _cell_volume 731.9(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3427 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 28.23 _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.548 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.459 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8167 _exptl_absorpt_correction_T_max 0.9686 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2001)' _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 'CCD Bruker APEX' _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 7409 _diffrn_reflns_av_R_equivalents 0.0499 _diffrn_reflns_av_sigmaI/netI 0.0604 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 25.25 _reflns_number_total 2654 _reflns_number_gt 1994 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2007)' _computing_cell_refinement 'SAINT (Bruker, 2007)' _computing_data_reduction 'SAINT (Bruker, 2007)' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _refine_special_details ; The final difference map has two peaks > 2 electrons/Angstroms^3^. These peaks were located about 0.9 Angstroms from the two chlorine atoms. The vector between the two chlorine atoms and the two large peaks in the difference map are approximately the same. Therefore, it is believed that these extra peaks represent an example of whole molecule disorder. ; _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^)+(0.1200P)^2^+0.4400P] 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 2654 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0933 _refine_ls_R_factor_gt 0.0700 _refine_ls_wR_factor_ref 0.1876 _refine_ls_wR_factor_gt 0.1702 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _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 0.9917(3) 0.15437(7) 0.34224(7) 0.0186(3) Uani 1 1 d . . . Cl2 Cl 0.0842(3) 0.77431(8) 0.17220(7) 0.0218(3) Uani 1 1 d . . . O1 O 0.2612(8) 0.3645(2) 0.5094(2) 0.0276(8) Uani 1 1 d . . . O2 O 0.5872(7) 0.2155(2) 0.50316(19) 0.0182(7) Uani 1 1 d . . . O3 O 1.0970(8) 0.3471(2) 0.0581(2) 0.0253(8) Uani 1 1 d . . . O4 O 1.2189(7) 0.2006(2) 0.15037(19) 0.0177(7) Uani 1 1 d . . . C1 C 0.5927(11) 0.3373(3) 0.3672(3) 0.0141(9) Uani 1 1 d . . . C2 C 0.8106(11) 0.2761(3) 0.3073(3) 0.0169(9) Uani 1 1 d . . . C3 C 0.8582(11) 0.3307(3) 0.2163(3) 0.0159(9) Uani 1 1 d . . . C4 C 0.6400(10) 0.5042(3) 0.1409(3) 0.0152(9) Uani 1 1 d . . . H4 H 0.7617 0.4875 0.0842 0.018 Uiso 1 1 calc R . . C5 C 0.4595(11) 0.6022(3) 0.1353(3) 0.0184(9) Uani 1 1 d . . . H5 H 0.4743 0.6423 0.0753 0.022 Uiso 1 1 calc R . . C6 C 0.2636(11) 0.6481(3) 0.2051(3) 0.0176(9) Uani 1 1 d . . . C7 C 0.1856(11) 0.6100(3) 0.2979(3) 0.0169(9) Uani 1 1 d . . . H7 H 0.0425 0.6551 0.3340 0.020 Uiso 1 1 calc R . . C8 C 0.2900(10) 0.5136(3) 0.3455(3) 0.0148(9) Uani 1 1 d . . . H8 H 0.2056 0.5021 0.4095 0.018 Uiso 1 1 calc R . . C9 C 0.5005(10) 0.4320(3) 0.3123(3) 0.0135(9) Uani 1 1 d . . . C10 C 0.6667(10) 0.4280(3) 0.2173(3) 0.0139(9) Uani 1 1 d . . . C11 C 0.4649(11) 0.3103(3) 0.4641(3) 0.0153(9) Uani 1 1 d . . . C12 C 0.4416(11) 0.1829(3) 0.5944(3) 0.0163(9) Uani 1 1 d . . . H12A H 0.1866 0.1917 0.5927 0.020 Uiso 1 1 calc R . . H12B H 0.5089 0.2236 0.6421 0.020 Uiso 1 1 calc R . . C13 C 0.5748(11) 0.0729(3) 0.6202(3) 0.0216(10) Uani 1 1 d . . . H13A H 0.4940 0.0327 0.5750 0.032 Uiso 1 1 calc R . . H13B H 0.4895 0.0499 0.6845 0.032 Uiso 1 1 calc R . . H13C H 0.8278 0.0645 0.6181 0.032 Uiso 1 1 calc R . . C14 C 1.0635(11) 0.2969(3) 0.1342(3) 0.0166(9) Uani 1 1 d . . . C15 C 1.4241(11) 0.1627(3) 0.0722(3) 0.0165(9) Uani 1 1 d . . . H15A H 1.5999 0.2080 0.0497 0.020 Uiso 1 1 calc R . . H15B H 1.2757 0.1592 0.0188 0.020 Uiso 1 1 calc R . . C16 C 1.5966(11) 0.0584(3) 0.1078(3) 0.0182(9) Uani 1 1 d . . . H16A H 1.7330 0.0623 0.1627 0.027 Uiso 1 1 calc R . . H16B H 1.7486 0.0318 0.0572 0.027 Uiso 1 1 calc R . . H16C H 1.4203 0.0133 0.1265 0.027 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 0.0240(6) 0.0118(5) 0.0175(5) 0.0007(4) 0.0027(4) 0.0034(4) Cl2 0.0278(7) 0.0140(6) 0.0211(6) 0.0016(4) -0.0008(5) 0.0031(4) O1 0.040(2) 0.0142(16) 0.0246(17) 0.0031(13) 0.0023(15) 0.0067(14) O2 0.0222(17) 0.0121(15) 0.0174(15) 0.0026(12) 0.0036(12) 0.0019(12) O3 0.0319(19) 0.0213(17) 0.0187(16) 0.0016(13) 0.0060(14) 0.0043(14) O4 0.0191(16) 0.0142(15) 0.0178(15) -0.0033(12) 0.0044(12) 0.0046(12) C1 0.016(2) 0.013(2) 0.014(2) -0.0027(16) -0.0014(16) -0.0034(17) C2 0.016(2) 0.022(2) 0.014(2) -0.0050(17) 0.0002(17) -0.0061(18) C3 0.014(2) 0.016(2) 0.019(2) -0.0071(17) -0.0016(17) -0.0012(17) C4 0.015(2) 0.020(2) 0.012(2) -0.0034(17) 0.0012(16) -0.0060(17) C5 0.018(2) 0.020(2) 0.016(2) 0.0007(17) -0.0003(17) -0.0013(18) C6 0.017(2) 0.013(2) 0.022(2) 0.0012(17) -0.0036(18) -0.0004(17) C7 0.017(2) 0.020(2) 0.014(2) -0.0031(17) 0.0003(17) -0.0031(18) C8 0.016(2) 0.016(2) 0.013(2) -0.0037(17) 0.0005(17) -0.0062(17) C9 0.015(2) 0.014(2) 0.013(2) -0.0031(16) -0.0014(16) -0.0030(17) C10 0.012(2) 0.014(2) 0.016(2) -0.0015(16) 0.0006(16) -0.0012(16) C11 0.018(2) 0.011(2) 0.017(2) -0.0024(17) -0.0036(17) 0.0008(17) C12 0.018(2) 0.013(2) 0.017(2) 0.0028(17) -0.0023(17) -0.0039(17) C13 0.022(2) 0.013(2) 0.027(2) 0.0044(18) -0.0007(19) 0.0016(18) C14 0.017(2) 0.015(2) 0.018(2) -0.0014(17) -0.0021(17) -0.0012(17) C15 0.015(2) 0.018(2) 0.015(2) -0.0023(17) 0.0028(17) 0.0019(17) C16 0.016(2) 0.019(2) 0.018(2) -0.0037(17) -0.0010(17) 0.0033(18) _geom_special_details ; ; 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 C2 1.714(4) . ? Cl2 C6 1.759(4) . ? O1 C11 1.220(5) . ? O2 C11 1.356(5) . ? O2 C12 1.426(5) . ? O3 C14 1.208(5) . ? O4 C14 1.351(5) . ? O4 C15 1.441(5) . ? C1 C9 1.417(5) . ? C1 C2 1.429(6) . ? C1 C11 1.457(6) . ? C2 C3 1.417(6) . ? C3 C10 1.419(6) . ? C3 C14 1.466(6) . ? C4 C10 1.390(5) . ? C4 C5 1.403(6) . ? C4 H4 0.9500 . ? C5 C6 1.379(6) . ? C5 H5 0.9500 . ? C6 C7 1.385(6) . ? C7 C8 1.401(6) . ? C7 H7 0.9500 . ? C8 C9 1.397(6) . ? C8 H8 0.9500 . ? C9 C10 1.470(6) . ? C12 C13 1.504(5) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C15 C16 1.508(5) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 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 C11 O2 C12 115.9(3) . . ? C14 O4 C15 116.1(3) . . ? C9 C1 C2 106.7(4) . . ? C9 C1 C11 124.4(4) . . ? C2 C1 C11 128.8(4) . . ? C3 C2 C1 110.4(4) . . ? C3 C2 Cl1 125.3(3) . . ? C1 C2 Cl1 124.3(3) . . ? C2 C3 C10 107.2(4) . . ? C2 C3 C14 128.4(4) . . ? C10 C3 C14 124.4(4) . . ? C10 C4 C5 129.5(4) . . ? C10 C4 H4 115.3 . . ? C5 C4 H4 115.3 . . ? C6 C5 C4 128.7(4) . . ? C6 C5 H5 115.7 . . ? C4 C5 H5 115.7 . . ? C5 C6 C7 129.7(4) . . ? C5 C6 Cl2 115.7(3) . . ? C7 C6 Cl2 114.6(3) . . ? C6 C7 C8 128.5(4) . . ? C6 C7 H7 115.7 . . ? C8 C7 H7 115.7 . . ? C9 C8 C7 129.2(4) . . ? C9 C8 H8 115.4 . . ? C7 C8 H8 115.4 . . ? C8 C9 C1 124.5(4) . . ? C8 C9 C10 127.4(3) . . ? C1 C9 C10 108.0(3) . . ? C4 C10 C3 125.4(4) . . ? C4 C10 C9 127.0(4) . . ? C3 C10 C9 107.6(3) . . ? O1 C11 O2 120.1(4) . . ? O1 C11 C1 125.5(4) . . ? O2 C11 C1 114.4(4) . . ? O2 C12 C13 108.0(3) . . ? O2 C12 H12A 110.1 . . ? C13 C12 H12A 110.1 . . ? O2 C12 H12B 110.1 . . ? C13 C12 H12B 110.1 . . ? H12A C12 H12B 108.4 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O3 C14 O4 121.0(4) . . ? O3 C14 C3 125.6(4) . . ? O4 C14 C3 113.4(3) . . ? O4 C15 C16 107.3(3) . . ? O4 C15 H15A 110.2 . . ? C16 C15 H15A 110.2 . . ? O4 C15 H15B 110.2 . . ? C16 C15 H15B 110.2 . . ? H15A C15 H15B 108.5 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 C1 C2 C3 0.3(5) . . . . ? C11 C1 C2 C3 177.0(4) . . . . ? C9 C1 C2 Cl1 179.5(3) . . . . ? C11 C1 C2 Cl1 -3.8(7) . . . . ? C1 C2 C3 C10 -0.4(5) . . . . ? Cl1 C2 C3 C10 -179.6(3) . . . . ? C1 C2 C3 C14 179.5(4) . . . . ? Cl1 C2 C3 C14 0.3(7) . . . . ? C10 C4 C5 C6 0.5(8) . . . . ? C4 C5 C6 C7 -1.7(8) . . . . ? C4 C5 C6 Cl2 178.3(4) . . . . ? C5 C6 C7 C8 0.6(8) . . . . ? Cl2 C6 C7 C8 -179.4(3) . . . . ? C6 C7 C8 C9 0.7(7) . . . . ? C7 C8 C9 C1 179.5(4) . . . . ? C7 C8 C9 C10 0.1(7) . . . . ? C2 C1 C9 C8 -179.6(4) . . . . ? C11 C1 C9 C8 3.5(6) . . . . ? C2 C1 C9 C10 -0.1(4) . . . . ? C11 C1 C9 C10 -177.0(4) . . . . ? C5 C4 C10 C3 -179.7(4) . . . . ? C5 C4 C10 C9 1.4(7) . . . . ? C2 C3 C10 C4 -178.7(4) . . . . ? C14 C3 C10 C4 1.4(7) . . . . ? C2 C3 C10 C9 0.4(5) . . . . ? C14 C3 C10 C9 -179.6(4) . . . . ? C8 C9 C10 C4 -1.6(7) . . . . ? C1 C9 C10 C4 178.9(4) . . . . ? C8 C9 C10 C3 179.3(4) . . . . ? C1 C9 C10 C3 -0.2(5) . . . . ? C12 O2 C11 O1 4.9(6) . . . . ? C12 O2 C11 C1 -174.1(3) . . . . ? C9 C1 C11 O1 1.1(7) . . . . ? C2 C1 C11 O1 -175.1(4) . . . . ? C9 C1 C11 O2 180.0(4) . . . . ? C2 C1 C11 O2 3.8(6) . . . . ? C11 O2 C12 C13 173.1(3) . . . . ? C15 O4 C14 O3 0.2(6) . . . . ? C15 O4 C14 C3 179.8(3) . . . . ? C2 C3 C14 O3 -179.5(4) . . . . ? C10 C3 C14 O3 0.4(7) . . . . ? C2 C3 C14 O4 0.9(6) . . . . ? C10 C3 C14 O4 -179.2(4) . . . . ? C14 O4 C15 C16 175.2(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 2.253 _refine_diff_density_min -0.309 _refine_diff_density_rms 0.124 #===END _database_code_depnum_ccdc_archive 'CCDC 941158' ####################################################################### # # 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_12027 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '[PPh3Au](1,3-diethoxycarbonyl-2-mercapto-6-azulenethiolate)' _chemical_melting_point '179 - 181' _chemical_formula_moiety 'C34 H30 Au O4 P S2' _chemical_formula_sum 'C34 H30 Au O4 P S2' _chemical_formula_weight 794.64 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' P P 0.1023 0.0942 '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' Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P c a 21' _symmetry_space_group_name_Hall 'P 2c -2ac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 23.574(2) _cell_length_b 11.1504(10) _cell_length_c 23.342(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6135.7(9) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7184 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 28.27 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.720 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3136 _exptl_absorpt_coefficient_mu 5.022 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2964 _exptl_absorpt_correction_T_max 0.5840 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2001)' _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 'CCD Bruker APEX' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 37712 _diffrn_reflns_av_R_equivalents 0.0404 _diffrn_reflns_av_sigmaI/netI 0.0431 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 25.50 _reflns_number_total 10050 _reflns_number_gt 9157 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2007)' _computing_cell_refinement 'SAINT (Bruker, 2007)' _computing_data_reduction 'SAINT (Bruker, 2007)' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _refine_special_details ; The selected crystal exhibited racemic twinning as shown by the refined value of the Flack parameter. ; _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^)+(0.0320P)^2^+11.4000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.240(6) _refine_ls_number_reflns 10050 _refine_ls_number_parameters 768 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0342 _refine_ls_R_factor_gt 0.0294 _refine_ls_wR_factor_ref 0.0721 _refine_ls_wR_factor_gt 0.0698 _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_restrained_S_all 0.998 _refine_ls_shift/su_max 0.030 _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 Au1A Au 0.511393(8) 0.22633(2) 0.546817(10) 0.01557(7) Uani 1 1 d . . . S1A S 0.75786(7) 0.91000(17) 0.47579(10) 0.0251(4) Uani 1 1 d . . . H1A H 0.762(3) 0.920(6) 0.527(3) 0.030 Uiso 1 1 d . . . S2A S 0.55849(7) 0.24323(15) 0.45997(8) 0.0179(4) Uani 1 1 d . . . P1A P 0.46345(7) 0.21203(15) 0.63066(9) 0.0149(4) Uani 1 1 d . . . O1A O 0.74025(19) 0.8309(4) 0.5987(2) 0.0236(11) Uani 1 1 d . . . O2A O 0.69756(19) 0.6607(4) 0.6216(2) 0.0232(11) Uani 1 1 d . . . O3A O 0.7198(2) 0.6713(5) 0.3262(2) 0.0332(13) Uani 1 1 d . . . O4A O 0.7378(2) 0.8551(4) 0.3603(2) 0.0265(12) Uani 1 1 d . . . C1A C 0.7030(3) 0.7079(6) 0.5239(3) 0.0156(16) Uani 1 1 d . . . C2A C 0.7206(3) 0.7738(6) 0.4760(3) 0.0190(16) Uani 1 1 d . . . C3A C 0.7044(3) 0.7116(7) 0.4256(3) 0.0209(17) Uani 1 1 d . . . C4A C 0.6498(3) 0.5259(6) 0.4043(3) 0.0191(16) Uani 1 1 d . . . H4A H 0.6570 0.5410 0.3649 0.023 Uiso 1 1 calc R . . C5A C 0.6172(3) 0.4266(6) 0.4150(3) 0.0194(16) Uani 1 1 d . . . H5A H 0.6039 0.3863 0.3818 0.023 Uiso 1 1 calc R . . C6A C 0.6004(3) 0.3744(6) 0.4672(3) 0.0168(15) Uani 1 1 d . . . C7A C 0.6166(3) 0.4156(6) 0.5209(3) 0.0195(16) Uani 1 1 d . . . H7A H 0.6044 0.3673 0.5521 0.023 Uiso 1 1 calc R . . C8A C 0.6473(2) 0.5144(5) 0.5360(3) 0.0178(14) Uani 1 1 d . . . H8A H 0.6520 0.5239 0.5762 0.021 Uiso 1 1 calc R . . C9A C 0.6731(3) 0.6044(6) 0.5035(3) 0.0179(15) Uani 1 1 d . . . C10A C 0.6737(3) 0.6077(6) 0.4417(3) 0.0184(16) Uani 1 1 d . . . C11A C 0.7158(3) 0.7405(7) 0.5823(4) 0.0223(19) Uani 1 1 d . . . C12A C 0.7105(3) 0.6860(7) 0.6821(3) 0.0246(18) Uani 1 1 d . . . H12A H 0.6924 0.7620 0.6942 0.030 Uiso 1 1 calc R . . H12B H 0.7520 0.6931 0.6878 0.030 Uiso 1 1 calc R . . C13A C 0.6874(3) 0.5826(6) 0.7165(3) 0.0248(17) Uani 1 1 d . . . H13A H 0.6460 0.5796 0.7124 0.037 Uiso 1 1 calc R . . H13B H 0.6972 0.5934 0.7570 0.037 Uiso 1 1 calc R . . H13C H 0.7039 0.5074 0.7025 0.037 Uiso 1 1 calc R . . C14A C 0.7205(3) 0.7417(6) 0.3660(3) 0.0235(17) Uani 1 1 d . . . C15A C 0.7605(3) 0.8880(8) 0.3049(3) 0.032(2) Uani 1 1 d . . . H15A H 0.7859 0.8233 0.2912 0.039 Uiso 1 1 calc R . . H15B H 0.7836 0.9618 0.3090 0.039 Uiso 1 1 calc R . . C16A C 0.7148(3) 0.9092(8) 0.2614(4) 0.037(2) Uani 1 1 d . . . H16A H 0.6865 0.9644 0.2772 0.056 Uiso 1 1 calc R . . H16B H 0.6966 0.8328 0.2518 0.056 Uiso 1 1 calc R . . H16C H 0.7315 0.9441 0.2268 0.056 Uiso 1 1 calc R . . C17A C 0.5108(2) 0.2192(6) 0.6929(4) 0.0181(18) Uani 1 1 d . . . C18A C 0.5569(3) 0.2974(6) 0.6900(3) 0.0191(15) Uani 1 1 d . . . H18A H 0.5645 0.3401 0.6556 0.023 Uiso 1 1 calc R . . C19A C 0.5915(3) 0.3127(7) 0.7369(3) 0.0224(16) Uani 1 1 d . . . H19A H 0.6225 0.3671 0.7353 0.027 Uiso 1 1 calc R . . C20A C 0.5812(3) 0.2497(7) 0.7857(4) 0.0271(17) Uani 1 1 d . . . H20A H 0.6051 0.2601 0.8180 0.032 Uiso 1 1 calc R . . C21A C 0.5366(3) 0.1711(7) 0.7885(4) 0.0293(18) Uani 1 1 d . . . H21A H 0.5305 0.1262 0.8225 0.035 Uiso 1 1 calc R . . C22A C 0.5005(3) 0.1564(8) 0.7427(4) 0.029(2) Uani 1 1 d . . . H22A H 0.4689 0.1038 0.7454 0.035 Uiso 1 1 calc R . . C23A C 0.4122(3) 0.3328(6) 0.6416(3) 0.0177(16) Uani 1 1 d . . . C24A C 0.3953(3) 0.4033(7) 0.5964(3) 0.0263(17) Uani 1 1 d . . . H24A H 0.4108 0.3909 0.5593 0.032 Uiso 1 1 calc R . . C25A C 0.3553(3) 0.4929(8) 0.6054(4) 0.035(2) Uani 1 1 d . . . H25A H 0.3432 0.5415 0.5742 0.042 Uiso 1 1 calc R . . C26A C 0.3331(3) 0.5116(7) 0.6590(3) 0.0233(17) Uani 1 1 d . . . H26A H 0.3059 0.5734 0.6646 0.028 Uiso 1 1 calc R . . C27A C 0.3496(3) 0.4428(7) 0.7045(4) 0.0263(18) Uani 1 1 d . . . H27A H 0.3338 0.4563 0.7414 0.032 Uiso 1 1 calc R . . C28A C 0.3896(3) 0.3530(6) 0.6966(3) 0.0208(15) Uani 1 1 d . . . H28A H 0.4017 0.3054 0.7280 0.025 Uiso 1 1 calc R . . C29A C 0.4230(3) 0.0748(6) 0.6387(3) 0.0152(16) Uani 1 1 d . . . C30A C 0.4504(3) -0.0317(7) 0.6509(3) 0.0225(17) Uani 1 1 d . . . H30A H 0.4903 -0.0323 0.6566 0.027 Uiso 1 1 calc R . . C31A C 0.4200(3) -0.1379(7) 0.6550(3) 0.0227(17) Uani 1 1 d . . . H31A H 0.4389 -0.2109 0.6637 0.027 Uiso 1 1 calc R . . C32A C 0.3619(3) -0.1360(7) 0.6461(3) 0.0192(17) Uani 1 1 d . . . H32A H 0.3408 -0.2084 0.6490 0.023 Uiso 1 1 calc R . . C33A C 0.3345(3) -0.0315(6) 0.6334(3) 0.0186(15) Uani 1 1 d . . . H33A H 0.2947 -0.0319 0.6269 0.022 Uiso 1 1 calc R . . C34A C 0.3644(2) 0.0747(6) 0.6298(3) 0.0161(15) Uani 1 1 d . . . H34A H 0.3452 0.1474 0.6214 0.019 Uiso 1 1 calc R . . Au1B Au 0.257865(8) 0.72326(2) 0.539559(10) 0.01562(7) Uani 1 1 d . . . S1B S 0.01475(7) 1.40395(16) 0.62809(9) 0.0242(4) Uani 1 1 d . . . H1B H 0.019(3) 1.428(6) 0.580(3) 0.029 Uiso 1 1 d . . . S2B S 0.21361(7) 0.73428(15) 0.62814(8) 0.0180(4) Uani 1 1 d . . . P1B P 0.30606(7) 0.71845(16) 0.45587(9) 0.0163(4) Uani 1 1 d . . . O1B O 0.02315(19) 1.3244(5) 0.5038(2) 0.0277(12) Uani 1 1 d . . . O2B O 0.07028(19) 1.1604(4) 0.4770(2) 0.0233(11) Uani 1 1 d . . . O3B O 0.0910(2) 1.1991(4) 0.7755(2) 0.0303(12) Uani 1 1 d . . . O4B O 0.0298(2) 1.3347(5) 0.7412(2) 0.0270(12) Uani 1 1 d . . . C1B C 0.0652(3) 1.1996(6) 0.5756(3) 0.0172(16) Uani 1 1 d . . . C2B C 0.0521(3) 1.2678(6) 0.6260(3) 0.0187(15) Uani 1 1 d . . . C3B C 0.0728(3) 1.2077(6) 0.6750(3) 0.0175(16) Uani 1 1 d . . . C4B C 0.1298(3) 1.0193(6) 0.6918(3) 0.0166(15) Uani 1 1 d . . . H4B H 0.1266 1.0349 0.7316 0.020 Uiso 1 1 calc R . . C5B C 0.1605(2) 0.9203(6) 0.6782(3) 0.0151(14) Uani 1 1 d . . . H5B H 0.1770 0.8806 0.7101 0.018 Uiso 1 1 calc R . . C6B C 0.1719(2) 0.8673(6) 0.6258(3) 0.0152(15) Uani 1 1 d . . . C7B C 0.1508(3) 0.9057(6) 0.5733(3) 0.0167(15) Uani 1 1 d . . . H7B H 0.1601 0.8552 0.5418 0.020 Uiso 1 1 calc R . . C8B C 0.1185(2) 1.0057(6) 0.5590(3) 0.0189(16) Uani 1 1 d . . . H8B H 0.1098 1.0132 0.5194 0.023 Uiso 1 1 calc R . . C9B C 0.0967(3) 1.0968(6) 0.5937(3) 0.0163(15) Uani 1 1 d . . . C10B C 0.1018(3) 1.1028(6) 0.6560(3) 0.0183(17) Uani 1 1 d . . . C11B C 0.0504(3) 1.2352(6) 0.5180(4) 0.0266(19) Uani 1 1 d . . . C12B C 0.0567(3) 1.1883(7) 0.4186(3) 0.0174(16) Uani 1 1 d . . . H12C H 0.0716 1.2685 0.4082 0.021 Uiso 1 1 calc R . . H12D H 0.0151 1.1880 0.4128 0.021 Uiso 1 1 calc R . . C13B C 0.0843(3) 1.0931(7) 0.3829(3) 0.0301(19) Uani 1 1 d . . . H13D H 0.1253 1.0932 0.3899 0.045 Uiso 1 1 calc R . . H13E H 0.0770 1.1091 0.3423 0.045 Uiso 1 1 calc R . . H13F H 0.0686 1.0146 0.3932 0.045 Uiso 1 1 calc R . . C14B C 0.0664(3) 1.2429(6) 0.7348(3) 0.0220(16) Uani 1 1 d . . . C15B C 0.0238(3) 1.3846(8) 0.7983(3) 0.029(2) Uani 1 1 d . . . H15C H 0.0603 1.4186 0.8116 0.035 Uiso 1 1 calc R . . H15D H 0.0117 1.3218 0.8256 0.035 Uiso 1 1 calc R . . C16B C -0.0204(3) 1.4812(8) 0.7943(3) 0.033(2) Uani 1 1 d . . . H16D H -0.0552 1.4478 0.7778 0.050 Uiso 1 1 calc R . . H16E H -0.0064 1.5461 0.7697 0.050 Uiso 1 1 calc R . . H16F H -0.0283 1.5128 0.8326 0.050 Uiso 1 1 calc R . . C17B C 0.2607(2) 0.7276(6) 0.3932(4) 0.0165(17) Uani 1 1 d . . . C18B C 0.2127(3) 0.8015(6) 0.3957(3) 0.0206(16) Uani 1 1 d . . . H18B H 0.2038 0.8422 0.4303 0.025 Uiso 1 1 calc R . . C19B C 0.1786(3) 0.8156(7) 0.3488(3) 0.0237(17) Uani 1 1 d . . . H19B H 0.1464 0.8668 0.3509 0.028 Uiso 1 1 calc R . . C20B C 0.1904(3) 0.7560(7) 0.2985(3) 0.030(2) Uani 1 1 d . . . H20B H 0.1665 0.7660 0.2660 0.036 Uiso 1 1 calc R . . C21B C 0.2379(3) 0.6806(8) 0.2953(4) 0.034(2) Uani 1 1 d . . . H21B H 0.2464 0.6393 0.2608 0.040 Uiso 1 1 calc R . . C22B C 0.2722(3) 0.6668(7) 0.3431(3) 0.0224(16) Uani 1 1 d . . . H22B H 0.3040 0.6147 0.3412 0.027 Uiso 1 1 calc R . . C23B C 0.3553(3) 0.8438(6) 0.4489(3) 0.0146(16) Uani 1 1 d . . . C24B C 0.3921(3) 0.8679(6) 0.4941(3) 0.0220(16) Uani 1 1 d . . . H24B H 0.3897 0.8225 0.5285 0.026 Uiso 1 1 calc R . . C25B C 0.4326(3) 0.9586(6) 0.4891(3) 0.0222(16) Uani 1 1 d . . . H25B H 0.4592 0.9721 0.5189 0.027 Uiso 1 1 calc R . . C26B C 0.4335(3) 1.0265(7) 0.4419(3) 0.0240(18) Uani 1 1 d . . . H26B H 0.4604 1.0897 0.4393 0.029 Uiso 1 1 calc R . . C27B C 0.3959(3) 1.0072(7) 0.3959(4) 0.0248(17) Uani 1 1 d . . . H27B H 0.3967 1.0569 0.3629 0.030 Uiso 1 1 calc R . . C28B C 0.3579(3) 0.9141(6) 0.4004(3) 0.0221(16) Uani 1 1 d . . . H28B H 0.3330 0.8979 0.3694 0.027 Uiso 1 1 calc R . . C29B C 0.3485(3) 0.5842(6) 0.4458(3) 0.0165(15) Uani 1 1 d . . . C30B C 0.3214(3) 0.4730(7) 0.4441(4) 0.0241(18) Uani 1 1 d . . . H30B H 0.2814 0.4691 0.4480 0.029 Uiso 1 1 calc R . . C31B C 0.3518(3) 0.3694(7) 0.4368(4) 0.031(2) Uani 1 1 d . . . H31B H 0.3326 0.2948 0.4334 0.037 Uiso 1 1 calc R . . C32B C 0.4111(3) 0.3736(7) 0.4343(3) 0.0220(18) Uani 1 1 d . . . H32B H 0.4322 0.3017 0.4299 0.026 Uiso 1 1 calc R . . C33B C 0.4389(3) 0.4827(6) 0.4382(3) 0.0226(16) Uani 1 1 d . . . H33B H 0.4792 0.4859 0.4369 0.027 Uiso 1 1 calc R . . C34B C 0.4079(3) 0.5857(7) 0.4438(3) 0.0202(16) Uani 1 1 d . . . H34B H 0.4272 0.6604 0.4464 0.024 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 Au1A 0.01425(10) 0.01741(12) 0.01504(15) -0.00006(17) 0.00060(12) -0.00208(8) S1A 0.0270(9) 0.0184(10) 0.0300(12) -0.0013(8) 0.0074(8) -0.0057(7) S2A 0.0178(8) 0.0208(9) 0.0151(10) -0.0014(7) 0.0008(7) -0.0046(7) P1A 0.0136(7) 0.0157(9) 0.0154(10) 0.0005(8) 0.0009(7) 0.0009(7) O1A 0.023(2) 0.021(3) 0.026(3) -0.001(2) -0.005(2) -0.011(2) O2A 0.025(2) 0.024(3) 0.021(3) -0.002(2) -0.004(2) -0.007(2) O3A 0.045(3) 0.025(3) 0.029(4) -0.001(3) 0.015(3) -0.008(3) O4A 0.036(3) 0.024(3) 0.019(3) 0.005(2) 0.007(2) -0.010(2) C1A 0.010(3) 0.016(4) 0.021(4) -0.002(3) 0.000(3) -0.003(3) C2A 0.014(3) 0.017(4) 0.026(4) -0.003(3) 0.006(3) 0.005(3) C3A 0.025(4) 0.019(4) 0.019(4) 0.004(3) 0.000(3) 0.007(3) C4A 0.021(3) 0.021(4) 0.015(4) -0.001(3) 0.005(3) 0.004(3) C5A 0.015(3) 0.024(4) 0.018(4) -0.005(3) -0.003(3) 0.002(3) C6A 0.014(3) 0.020(4) 0.016(4) 0.008(3) -0.001(3) 0.000(3) C7A 0.025(3) 0.017(4) 0.017(4) 0.003(3) 0.000(3) -0.002(3) C8A 0.013(3) 0.027(3) 0.014(4) 0.001(3) -0.004(3) -0.002(2) C9A 0.016(3) 0.018(4) 0.019(4) 0.004(3) 0.002(3) 0.007(3) C10A 0.012(3) 0.022(4) 0.021(4) -0.001(3) -0.001(3) 0.007(3) C11A 0.007(3) 0.015(4) 0.045(6) 0.008(3) -0.001(3) -0.003(3) C12A 0.026(4) 0.031(5) 0.017(4) -0.009(3) -0.009(3) 0.001(3) C13A 0.028(3) 0.021(4) 0.025(5) -0.001(3) -0.005(3) -0.003(3) C14A 0.024(4) 0.019(4) 0.027(5) 0.004(3) 0.003(3) -0.003(3) C15A 0.034(5) 0.035(5) 0.028(6) 0.006(4) 0.003(3) -0.016(4) C16A 0.046(5) 0.031(5) 0.034(5) -0.006(4) 0.014(4) 0.011(4) C17A 0.014(3) 0.019(4) 0.022(5) -0.001(3) 0.003(3) 0.003(3) C18A 0.027(3) 0.008(3) 0.022(4) 0.003(3) -0.005(3) 0.002(3) C19A 0.020(3) 0.020(4) 0.027(5) -0.004(3) -0.001(3) 0.000(3) C20A 0.024(3) 0.039(5) 0.018(4) 0.000(4) -0.004(3) 0.004(3) C21A 0.021(4) 0.042(5) 0.024(4) 0.010(4) -0.002(3) 0.002(3) C22A 0.017(3) 0.044(5) 0.027(5) 0.006(4) 0.006(3) -0.005(3) C23A 0.015(3) 0.012(4) 0.027(5) -0.006(3) -0.001(3) -0.005(3) C24A 0.025(4) 0.034(5) 0.020(4) 0.008(3) 0.008(3) 0.007(3) C25A 0.037(4) 0.045(5) 0.024(5) 0.022(4) -0.001(4) 0.013(4) C26A 0.025(4) 0.015(4) 0.031(5) -0.004(4) 0.003(3) 0.003(3) C27A 0.020(3) 0.035(5) 0.024(5) -0.009(4) -0.001(3) 0.000(3) C28A 0.022(3) 0.024(4) 0.016(4) 0.007(3) -0.002(3) 0.002(3) C29A 0.017(3) 0.017(4) 0.011(4) -0.001(3) 0.003(3) -0.002(3) C30A 0.010(3) 0.031(5) 0.026(5) 0.004(3) 0.001(3) 0.007(3) C31A 0.021(3) 0.022(4) 0.026(5) 0.004(3) 0.002(3) 0.004(3) C32A 0.020(4) 0.021(4) 0.017(4) -0.003(3) 0.008(3) -0.007(3) C33A 0.018(3) 0.027(4) 0.011(4) -0.003(3) 0.001(3) 0.002(3) C34A 0.019(3) 0.010(3) 0.019(4) -0.001(3) -0.005(3) 0.005(3) Au1B 0.01356(10) 0.01711(12) 0.01619(15) -0.00022(17) 0.00144(12) 0.00172(8) S1B 0.0289(9) 0.0178(9) 0.0258(12) 0.0000(8) -0.0007(8) 0.0049(7) S2B 0.0177(8) 0.0192(9) 0.0171(10) 0.0027(8) 0.0015(7) 0.0037(7) P1B 0.0144(8) 0.0165(9) 0.0181(11) -0.0020(8) 0.0019(7) 0.0005(7) O1B 0.025(2) 0.031(3) 0.027(3) 0.001(2) -0.005(2) 0.003(2) O2B 0.029(3) 0.022(3) 0.019(3) -0.003(2) -0.002(2) 0.006(2) O3B 0.042(3) 0.026(3) 0.023(3) -0.006(2) -0.001(3) 0.012(2) O4B 0.029(3) 0.031(3) 0.022(3) -0.002(2) 0.002(2) 0.012(2) C1B 0.011(3) 0.017(4) 0.023(4) -0.007(3) -0.001(3) -0.005(3) C2B 0.017(3) 0.015(4) 0.024(4) -0.003(3) -0.002(3) -0.006(3) C3B 0.012(3) 0.020(4) 0.021(4) 0.001(3) 0.001(3) -0.006(3) C4B 0.019(3) 0.022(4) 0.008(4) -0.001(3) -0.006(3) -0.006(3) C5B 0.016(3) 0.019(4) 0.011(4) 0.002(3) -0.005(3) 0.004(3) C6B 0.010(3) 0.017(4) 0.019(4) 0.002(3) 0.000(3) -0.007(2) C7B 0.016(3) 0.021(4) 0.014(4) -0.005(3) 0.000(3) -0.002(3) C8B 0.016(3) 0.022(4) 0.019(4) 0.001(3) -0.005(3) -0.002(3) C9B 0.017(3) 0.014(4) 0.018(4) 0.000(3) 0.001(3) -0.001(3) C10B 0.015(3) 0.012(4) 0.029(5) 0.000(3) -0.005(3) 0.000(3) C11B 0.024(4) 0.010(4) 0.046(5) -0.003(3) -0.005(3) 0.003(3) C12B 0.017(3) 0.023(4) 0.012(4) 0.008(3) -0.005(3) 0.004(3) C13B 0.032(4) 0.038(5) 0.021(5) -0.003(4) -0.013(3) 0.004(4) C14B 0.018(3) 0.023(4) 0.026(5) 0.001(3) 0.003(3) 0.001(3) C15B 0.034(4) 0.032(5) 0.021(6) -0.006(3) 0.005(3) 0.003(4) C16B 0.035(4) 0.032(5) 0.033(6) 0.004(3) 0.017(4) 0.011(3) C17B 0.015(3) 0.014(4) 0.021(5) -0.001(3) 0.001(3) -0.009(3) C18B 0.022(3) 0.020(4) 0.020(4) -0.005(3) 0.005(3) 0.001(3) C19B 0.025(4) 0.023(4) 0.023(5) 0.002(3) 0.001(3) 0.007(3) C20B 0.033(4) 0.029(5) 0.028(6) 0.007(3) -0.004(3) 0.000(4) C21B 0.034(5) 0.036(4) 0.031(6) -0.010(4) 0.005(4) 0.002(3) C22B 0.021(3) 0.029(4) 0.017(4) -0.004(3) 0.001(3) -0.003(3) C23B 0.015(3) 0.009(3) 0.020(4) 0.000(3) 0.007(3) 0.003(3) C24B 0.029(4) 0.017(4) 0.020(4) -0.004(3) 0.001(3) -0.005(3) C25B 0.017(3) 0.025(4) 0.024(5) -0.003(3) -0.002(3) -0.005(3) C26B 0.021(4) 0.017(4) 0.034(5) -0.015(4) 0.000(3) -0.005(3) C27B 0.023(3) 0.023(4) 0.029(5) 0.002(3) 0.002(3) 0.003(3) C28B 0.019(3) 0.021(4) 0.027(5) -0.005(3) -0.001(3) 0.003(3) C29B 0.010(3) 0.023(4) 0.016(4) -0.006(3) 0.002(3) -0.001(3) C30B 0.014(3) 0.022(4) 0.037(5) -0.003(4) 0.003(3) -0.008(3) C31B 0.033(4) 0.015(4) 0.045(6) -0.006(4) -0.002(4) -0.001(3) C32B 0.027(4) 0.016(4) 0.023(5) 0.000(3) 0.004(3) 0.004(3) C33B 0.017(3) 0.026(4) 0.025(4) 0.000(3) 0.000(3) 0.000(3) C34B 0.018(3) 0.022(4) 0.020(4) 0.003(3) 0.003(3) -0.003(3) _geom_special_details ; ; 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 Au1A P1A 2.2655(19) . ? Au1A S2A 2.3190(19) . ? S1A C2A 1.755(7) . ? S1A H1A 1.20(8) . ? S2A C6A 1.772(7) . ? P1A C29A 1.813(7) . ? P1A C23A 1.827(7) . ? P1A C17A 1.833(8) . ? O1A C11A 1.223(9) . ? O2A C11A 1.348(9) . ? O2A C12A 1.473(9) . ? O3A C14A 1.217(9) . ? O4A C14A 1.336(8) . ? O4A C15A 1.447(9) . ? C1A C2A 1.401(10) . ? C1A C9A 1.434(10) . ? C1A C11A 1.442(11) . ? C2A C3A 1.417(11) . ? C3A C10A 1.417(10) . ? C3A C14A 1.479(11) . ? C4A C5A 1.370(9) . ? C4A C10A 1.383(10) . ? C4A H4A 0.9500 . ? C5A C6A 1.408(10) . ? C5A H5A 0.9500 . ? C6A C7A 1.389(10) . ? C7A C8A 1.365(9) . ? C7A H7A 0.9500 . ? C8A C9A 1.398(9) . ? C8A H8A 0.9500 . ? C9A C10A 1.441(10) . ? C12A C13A 1.507(10) . ? C12A H12A 0.9900 . ? C12A H12B 0.9900 . ? C13A H13A 0.9800 . ? C13A H13B 0.9800 . ? C13A H13C 0.9800 . ? C15A C16A 1.500(11) . ? C15A H15A 0.9900 . ? C15A H15B 0.9900 . ? C16A H16A 0.9800 . ? C16A H16B 0.9800 . ? C16A H16C 0.9800 . ? C17A C22A 1.380(11) . ? C17A C18A 1.397(9) . ? C18A C19A 1.376(10) . ? C18A H18A 0.9500 . ? C19A C20A 1.360(11) . ? C19A H19A 0.9500 . ? C20A C21A 1.370(10) . ? C20A H20A 0.9500 . ? C21A C22A 1.376(11) . ? C21A H21A 0.9500 . ? C22A H22A 0.9500 . ? C23A C24A 1.375(10) . ? C23A C28A 1.407(10) . ? C24A C25A 1.390(10) . ? C24A H24A 0.9500 . ? C25A C26A 1.373(11) . ? C25A H25A 0.9500 . ? C26A C27A 1.368(11) . ? C26A H26A 0.9500 . ? C27A C28A 1.388(9) . ? C27A H27A 0.9500 . ? C28A H28A 0.9500 . ? C29A C30A 1.381(9) . ? C29A C34A 1.397(9) . ? C30A C31A 1.386(10) . ? C30A H30A 0.9500 . ? C31A C32A 1.386(9) . ? C31A H31A 0.9500 . ? C32A C33A 1.365(10) . ? C32A H32A 0.9500 . ? C33A C34A 1.380(9) . ? C33A H33A 0.9500 . ? C34A H34A 0.9500 . ? Au1B P1B 2.260(2) . ? Au1B S2B 2.3191(19) . ? S1B C2B 1.756(7) . ? S1B H1B 1.15(8) . ? S2B C6B 1.780(7) . ? P1B C17B 1.815(8) . ? P1B C29B 1.816(7) . ? P1B C23B 1.823(7) . ? O1B C11B 1.229(9) . ? O2B C11B 1.354(9) . ? O2B C12B 1.434(8) . ? O3B C14B 1.216(9) . ? O4B C14B 1.347(8) . ? O4B C15B 1.451(8) . ? C1B C9B 1.429(10) . ? C1B C2B 1.434(10) . ? C1B C11B 1.444(11) . ? C2B C3B 1.412(10) . ? C3B C10B 1.426(10) . ? C3B C14B 1.458(10) . ? C4B C5B 1.357(9) . ? C4B C10B 1.413(9) . ? C4B H4B 0.9500 . ? C5B C6B 1.386(10) . ? C5B H5B 0.9500 . ? C6B C7B 1.391(10) . ? C7B C8B 1.392(9) . ? C7B H7B 0.9500 . ? C8B C9B 1.396(9) . ? C8B H8B 0.9500 . ? C9B C10B 1.462(10) . ? C12B C13B 1.498(10) . ? C12B H12C 0.9900 . ? C12B H12D 0.9900 . ? C13B H13D 0.9800 . ? C13B H13E 0.9800 . ? C13B H13F 0.9800 . ? C15B C16B 1.501(11) . ? C15B H15C 0.9900 . ? C15B H15D 0.9900 . ? C16B H16D 0.9800 . ? C16B H16E 0.9800 . ? C16B H16F 0.9800 . ? C17B C22B 1.379(11) . ? C17B C18B 1.401(9) . ? C18B C19B 1.369(10) . ? C18B H18B 0.9500 . ? C19B C20B 1.378(11) . ? C19B H19B 0.9500 . ? C20B C21B 1.401(11) . ? C20B H20B 0.9500 . ? C21B C22B 1.385(11) . ? C21B H21B 0.9500 . ? C22B H22B 0.9500 . ? C23B C28B 1.378(10) . ? C23B C24B 1.394(10) . ? C24B C25B 1.394(9) . ? C24B H24B 0.9500 . ? C25B C26B 1.336(11) . ? C25B H25B 0.9500 . ? C26B C27B 1.408(10) . ? C26B H26B 0.9500 . ? C27B C28B 1.374(10) . ? C27B H27B 0.9500 . ? C28B H28B 0.9500 . ? C29B C30B 1.396(9) . ? C29B C34B 1.401(8) . ? C30B C31B 1.369(10) . ? C30B H30B 0.9500 . ? C31B C32B 1.400(10) . ? C31B H31B 0.9500 . ? C32B C33B 1.385(10) . ? C32B H32B 0.9500 . ? C33B C34B 1.368(10) . ? C33B H33B 0.9500 . ? C34B H34B 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 P1A Au1A S2A 178.56(6) . . ? C2A S1A H1A 97(3) . . ? C6A S2A Au1A 104.5(2) . . ? C29A P1A C23A 105.1(3) . . ? C29A P1A C17A 105.9(3) . . ? C23A P1A C17A 105.1(3) . . ? C29A P1A Au1A 114.3(2) . . ? C23A P1A Au1A 113.5(3) . . ? C17A P1A Au1A 112.2(2) . . ? C11A O2A C12A 117.4(6) . . ? C14A O4A C15A 116.3(6) . . ? C2A C1A C9A 107.5(6) . . ? C2A C1A C11A 124.1(6) . . ? C9A C1A C11A 128.3(6) . . ? C1A C2A C3A 109.1(6) . . ? C1A C2A S1A 127.1(6) . . ? C3A C2A S1A 123.8(6) . . ? C2A C3A C10A 108.5(7) . . ? C2A C3A C14A 126.8(7) . . ? C10A C3A C14A 124.5(7) . . ? C5A C4A C10A 130.3(7) . . ? C5A C4A H4A 114.9 . . ? C10A C4A H4A 114.9 . . ? C4A C5A C6A 130.5(7) . . ? C4A C5A H5A 114.7 . . ? C6A C5A H5A 114.7 . . ? C7A C6A C5A 124.5(6) . . ? C7A C6A S2A 120.8(5) . . ? C5A C6A S2A 114.6(5) . . ? C8A C7A C6A 130.3(7) . . ? C8A C7A H7A 114.9 . . ? C6A C7A H7A 114.9 . . ? C7A C8A C9A 132.1(7) . . ? C7A C8A H8A 114.0 . . ? C9A C8A H8A 114.0 . . ? C8A C9A C1A 127.6(7) . . ? C8A C9A C10A 124.5(7) . . ? C1A C9A C10A 107.9(6) . . ? C4A C10A C3A 125.4(7) . . ? C4A C10A C9A 127.7(7) . . ? C3A C10A C9A 106.9(7) . . ? O1A C11A O2A 118.8(7) . . ? O1A C11A C1A 127.0(7) . . ? O2A C11A C1A 114.1(6) . . ? O2A C12A C13A 106.8(6) . . ? O2A C12A H12A 110.4 . . ? C13A C12A H12A 110.4 . . ? O2A C12A H12B 110.4 . . ? C13A C12A H12B 110.4 . . ? H12A C12A H12B 108.6 . . ? C12A C13A H13A 109.5 . . ? C12A C13A H13B 109.5 . . ? H13A C13A H13B 109.5 . . ? C12A C13A H13C 109.5 . . ? H13A C13A H13C 109.5 . . ? H13B C13A H13C 109.5 . . ? O3A C14A O4A 122.5(7) . . ? O3A C14A C3A 124.7(7) . . ? O4A C14A C3A 112.8(7) . . ? O4A C15A C16A 112.3(6) . . ? O4A C15A H15A 109.2 . . ? C16A C15A H15A 109.2 . . ? O4A C15A H15B 109.2 . . ? C16A C15A H15B 109.2 . . ? H15A C15A H15B 107.9 . . ? C15A C16A H16A 109.5 . . ? C15A C16A H16B 109.5 . . ? H16A C16A H16B 109.5 . . ? C15A C16A H16C 109.5 . . ? H16A C16A H16C 109.5 . . ? H16B C16A H16C 109.5 . . ? C22A C17A C18A 119.7(7) . . ? C22A C17A P1A 122.6(5) . . ? C18A C17A P1A 117.6(6) . . ? C19A C18A C17A 120.0(7) . . ? C19A C18A H18A 120.0 . . ? C17A C18A H18A 120.0 . . ? C20A C19A C18A 119.8(7) . . ? C20A C19A H19A 120.1 . . ? C18A C19A H19A 120.1 . . ? C19A C20A C21A 120.6(8) . . ? C19A C20A H20A 119.7 . . ? C21A C20A H20A 119.7 . . ? C20A C21A C22A 120.9(8) . . ? C20A C21A H21A 119.5 . . ? C22A C21A H21A 119.5 . . ? C21A C22A C17A 119.0(7) . . ? C21A C22A H22A 120.5 . . ? C17A C22A H22A 120.5 . . ? C24A C23A C28A 119.9(6) . . ? C24A C23A P1A 120.4(6) . . ? C28A C23A P1A 119.7(6) . . ? C23A C24A C25A 119.5(7) . . ? C23A C24A H24A 120.3 . . ? C25A C24A H24A 120.3 . . ? C26A C25A C24A 120.4(7) . . ? C26A C25A H25A 119.8 . . ? C24A C25A H25A 119.8 . . ? C27A C26A C25A 121.0(7) . . ? C27A C26A H26A 119.5 . . ? C25A C26A H26A 119.5 . . ? C26A C27A C28A 119.6(7) . . ? C26A C27A H27A 120.2 . . ? C28A C27A H27A 120.2 . . ? C27A C28A C23A 119.6(7) . . ? C27A C28A H28A 120.2 . . ? C23A C28A H28A 120.2 . . ? C30A C29A C34A 119.4(6) . . ? C30A C29A P1A 120.1(5) . . ? C34A C29A P1A 120.4(5) . . ? C29A C30A C31A 120.5(6) . . ? C29A C30A H30A 119.7 . . ? C31A C30A H30A 119.7 . . ? C30A C31A C32A 119.2(7) . . ? C30A C31A H31A 120.4 . . ? C32A C31A H31A 120.4 . . ? C33A C32A C31A 120.8(7) . . ? C33A C32A H32A 119.6 . . ? C31A C32A H32A 119.6 . . ? C32A C33A C34A 120.3(6) . . ? C32A C33A H33A 119.9 . . ? C34A C33A H33A 119.9 . . ? C33A C34A C29A 119.8(6) . . ? C33A C34A H34A 120.1 . . ? C29A C34A H34A 120.1 . . ? P1B Au1B S2B 176.20(6) . . ? C2B S1B H1B 97(4) . . ? C6B S2B Au1B 105.4(2) . . ? C17B P1B C29B 105.5(3) . . ? C17B P1B C23B 105.0(3) . . ? C29B P1B C23B 105.6(3) . . ? C17B P1B Au1B 113.5(2) . . ? C29B P1B Au1B 114.1(2) . . ? C23B P1B Au1B 112.3(2) . . ? C11B O2B C12B 117.5(6) . . ? C14B O4B C15B 117.1(6) . . ? C9B C1B C2B 107.2(7) . . ? C9B C1B C11B 128.3(6) . . ? C2B C1B C11B 124.4(6) . . ? C3B C2B C1B 109.7(6) . . ? C3B C2B S1B 124.1(6) . . ? C1B C2B S1B 126.1(6) . . ? C2B C3B C10B 107.7(7) . . ? C2B C3B C14B 127.7(7) . . ? C10B C3B C14B 124.5(7) . . ? C5B C4B C10B 130.3(7) . . ? C5B C4B H4B 114.8 . . ? C10B C4B H4B 114.8 . . ? C4B C5B C6B 131.0(7) . . ? C4B C5B H5B 114.5 . . ? C6B C5B H5B 114.5 . . ? C5B C6B C7B 125.3(6) . . ? C5B C6B S2B 115.8(5) . . ? C7B C6B S2B 118.8(5) . . ? C6B C7B C8B 130.8(7) . . ? C6B C7B H7B 114.6 . . ? C8B C7B H7B 114.6 . . ? C7B C8B C9B 130.2(7) . . ? C7B C8B H8B 114.9 . . ? C9B C8B H8B 114.9 . . ? C8B C9B C1B 127.1(7) . . ? C8B C9B C10B 125.4(6) . . ? C1B C9B C10B 107.5(6) . . ? C4B C10B C3B 125.6(7) . . ? C4B C10B C9B 126.6(6) . . ? C3B C10B C9B 107.8(6) . . ? O1B C11B O2B 119.2(8) . . ? O1B C11B C1B 126.9(7) . . ? O2B C11B C1B 113.9(6) . . ? O2B C12B C13B 106.1(6) . . ? O2B C12B H12C 110.5 . . ? C13B C12B H12C 110.5 . . ? O2B C12B H12D 110.5 . . ? C13B C12B H12D 110.5 . . ? H12C C12B H12D 108.7 . . ? C12B C13B H13D 109.5 . . ? C12B C13B H13E 109.5 . . ? H13D C13B H13E 109.5 . . ? C12B C13B H13F 109.5 . . ? H13D C13B H13F 109.5 . . ? H13E C13B H13F 109.5 . . ? O3B C14B O4B 121.6(7) . . ? O3B C14B C3B 126.3(6) . . ? O4B C14B C3B 112.1(6) . . ? O4B C15B C16B 106.6(6) . . ? O4B C15B H15C 110.4 . . ? C16B C15B H15C 110.4 . . ? O4B C15B H15D 110.4 . . ? C16B C15B H15D 110.4 . . ? H15C C15B H15D 108.6 . . ? C15B C16B H16D 109.5 . . ? C15B C16B H16E 109.5 . . ? H16D C16B H16E 109.5 . . ? C15B C16B H16F 109.5 . . ? H16D C16B H16F 109.5 . . ? H16E C16B H16F 109.5 . . ? C22B C17B C18B 118.9(7) . . ? C22B C17B P1B 122.7(5) . . ? C18B C17B P1B 118.3(6) . . ? C19B C18B C17B 120.6(7) . . ? C19B C18B H18B 119.7 . . ? C17B C18B H18B 119.7 . . ? C18B C19B C20B 120.5(7) . . ? C18B C19B H19B 119.8 . . ? C20B C19B H19B 119.8 . . ? C19B C20B C21B 119.7(7) . . ? C19B C20B H20B 120.1 . . ? C21B C20B H20B 120.1 . . ? C22B C21B C20B 119.4(8) . . ? C22B C21B H21B 120.3 . . ? C20B C21B H21B 120.3 . . ? C17B C22B C21B 120.9(7) . . ? C17B C22B H22B 119.6 . . ? C21B C22B H22B 119.6 . . ? C28B C23B C24B 118.9(7) . . ? C28B C23B P1B 122.6(6) . . ? C24B C23B P1B 118.5(5) . . ? C25B C24B C23B 120.2(7) . . ? C25B C24B H24B 119.9 . . ? C23B C24B H24B 119.9 . . ? C26B C25B C24B 119.4(7) . . ? C26B C25B H25B 120.3 . . ? C24B C25B H25B 120.3 . . ? C25B C26B C27B 122.1(7) . . ? C25B C26B H26B 119.0 . . ? C27B C26B H26B 119.0 . . ? C28B C27B C26B 117.8(8) . . ? C28B C27B H27B 121.1 . . ? C26B C27B H27B 121.1 . . ? C27B C28B C23B 121.5(7) . . ? C27B C28B H28B 119.3 . . ? C23B C28B H28B 119.3 . . ? C30B C29B C34B 117.8(6) . . ? C30B C29B P1B 118.9(5) . . ? C34B C29B P1B 123.0(5) . . ? C31B C30B C29B 121.0(6) . . ? C31B C30B H30B 119.5 . . ? C29B C30B H30B 119.5 . . ? C30B C31B C32B 119.9(7) . . ? C30B C31B H31B 120.1 . . ? C32B C31B H31B 120.1 . . ? C33B C32B C31B 120.0(7) . . ? C33B C32B H32B 120.0 . . ? C31B C32B H32B 120.0 . . ? C34B C33B C32B 119.4(6) . . ? C34B C33B H33B 120.3 . . ? C32B C33B H33B 120.3 . . ? C33B C34B C29B 121.8(7) . . ? C33B C34B H34B 119.1 . . ? C29B C34B H34B 119.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag #P1A Au1A S2A C6A 98(2) . . . . ? #S2A Au1A P1A C29A 90(2) . . . . ? #S2A Au1A P1A C23A -31(2) . . . . ? #S2A Au1A P1A C17A -150(2) . . . . ? #P1B Au1B S2B C6B 95.6(9) . . . . ? #S2B Au1B P1B C17B -149.7(9) . . . . ? #S2B Au1B P1B C29B 89.4(10) . . . . ? #S2B Au1B P1B C23B -30.7(10) . . . . ? C9A C1A C2A C3A -2.2(8) . . . . ? C11A C1A C2A C3A 175.6(7) . . . . ? C9A C1A C2A S1A 178.8(5) . . . . ? C11A C1A C2A S1A -3.4(10) . . . . ? C1A C2A C3A C10A 2.8(8) . . . . ? S1A C2A C3A C10A -178.2(5) . . . . ? C1A C2A C3A C14A -172.1(7) . . . . ? S1A C2A C3A C14A 6.9(10) . . . . ? C10A C4A C5A C6A -3.2(12) . . . . ? C4A C5A C6A C7A -2.4(11) . . . . ? C4A C5A C6A S2A -179.2(6) . . . . ? Au1A S2A C6A C7A 24.2(6) . . . . ? Au1A S2A C6A C5A -158.9(4) . . . . ? C5A C6A C7A C8A 4.9(11) . . . . ? S2A C6A C7A C8A -178.5(5) . . . . ? C6A C7A C8A C9A -1.3(12) . . . . ? C7A C8A C9A C1A 177.4(7) . . . . ? C7A C8A C9A C10A -2.3(11) . . . . ? C2A C1A C9A C8A -178.9(6) . . . . ? C11A C1A C9A C8A 3.4(12) . . . . ? C2A C1A C9A C10A 0.8(7) . . . . ? C11A C1A C9A C10A -176.8(7) . . . . ? C5A C4A C10A C3A -176.5(7) . . . . ? C5A C4A C10A C9A 4.2(12) . . . . ? C2A C3A C10A C4A 178.4(6) . . . . ? C14A C3A C10A C4A -6.6(11) . . . . ? C2A C3A C10A C9A -2.2(8) . . . . ? C14A C3A C10A C9A 172.9(6) . . . . ? C8A C9A C10A C4A 0.0(11) . . . . ? C1A C9A C10A C4A -179.7(6) . . . . ? C8A C9A C10A C3A -179.4(6) . . . . ? C1A C9A C10A C3A 0.8(7) . . . . ? C12A O2A C11A O1A -2.4(9) . . . . ? C12A O2A C11A C1A 178.3(6) . . . . ? C2A C1A C11A O1A 4.5(12) . . . . ? C9A C1A C11A O1A -178.2(6) . . . . ? C2A C1A C11A O2A -176.2(6) . . . . ? C9A C1A C11A O2A 1.1(11) . . . . ? C11A O2A C12A C13A -178.3(6) . . . . ? C15A O4A C14A O3A -5.1(10) . . . . ? C15A O4A C14A C3A 173.1(6) . . . . ? C2A C3A C14A O3A 158.3(7) . . . . ? C10A C3A C14A O3A -15.8(12) . . . . ? C2A C3A C14A O4A -19.8(10) . . . . ? C10A C3A C14A O4A 166.1(6) . . . . ? C14A O4A C15A C16A 78.1(9) . . . . ? C29A P1A C17A C22A -21.0(7) . . . . ? C23A P1A C17A C22A 89.9(7) . . . . ? Au1A P1A C17A C22A -146.3(6) . . . . ? C29A P1A C17A C18A 163.1(5) . . . . ? C23A P1A C17A C18A -86.1(6) . . . . ? Au1A P1A C17A C18A 37.7(6) . . . . ? C22A C17A C18A C19A -0.7(10) . . . . ? P1A C17A C18A C19A 175.4(5) . . . . ? C17A C18A C19A C20A 1.3(10) . . . . ? C18A C19A C20A C21A -0.1(11) . . . . ? C19A C20A C21A C22A -1.6(12) . . . . ? C20A C21A C22A C17A 2.1(12) . . . . ? C18A C17A C22A C21A -1.0(11) . . . . ? P1A C17A C22A C21A -176.9(6) . . . . ? C29A P1A C23A C24A -109.6(6) . . . . ? C17A P1A C23A C24A 138.9(6) . . . . ? Au1A P1A C23A C24A 16.0(6) . . . . ? C29A P1A C23A C28A 70.0(6) . . . . ? C17A P1A C23A C28A -41.6(6) . . . . ? Au1A P1A C23A C28A -164.5(5) . . . . ? C28A C23A C24A C25A -1.0(11) . . . . ? P1A C23A C24A C25A 178.5(6) . . . . ? C23A C24A C25A C26A 0.5(12) . . . . ? C24A C25A C26A C27A -0.2(12) . . . . ? C25A C26A C27A C28A 0.4(11) . . . . ? C26A C27A C28A C23A -0.8(10) . . . . ? C24A C23A C28A C27A 1.1(10) . . . . ? P1A C23A C28A C27A -178.4(5) . . . . ? C23A P1A C29A C30A -159.7(6) . . . . ? C17A P1A C29A C30A -48.8(7) . . . . ? Au1A P1A C29A C30A 75.2(7) . . . . ? C23A P1A C29A C34A 23.5(7) . . . . ? C17A P1A C29A C34A 134.4(6) . . . . ? Au1A P1A C29A C34A -101.5(6) . . . . ? C34A C29A C30A C31A -0.7(11) . . . . ? P1A C29A C30A C31A -177.5(6) . . . . ? C29A C30A C31A C32A 0.6(11) . . . . ? C30A C31A C32A C33A 0.2(11) . . . . ? C31A C32A C33A C34A -0.8(11) . . . . ? C32A C33A C34A C29A 0.7(11) . . . . ? C30A C29A C34A C33A 0.1(11) . . . . ? P1A C29A C34A C33A 176.8(6) . . . . ? C9B C1B C2B C3B -2.2(7) . . . . ? C11B C1B C2B C3B -179.7(7) . . . . ? C9B C1B C2B S1B 179.0(5) . . . . ? C11B C1B C2B S1B 1.5(10) . . . . ? C1B C2B C3B C10B 2.7(7) . . . . ? S1B C2B C3B C10B -178.5(5) . . . . ? C1B C2B C3B C14B -177.0(6) . . . . ? S1B C2B C3B C14B 1.8(10) . . . . ? C10B C4B C5B C6B -3.3(12) . . . . ? C4B C5B C6B C7B -2.6(11) . . . . ? C4B C5B C6B S2B -178.7(6) . . . . ? Au1B S2B C6B C5B -154.3(4) . . . . ? Au1B S2B C6B C7B 29.4(5) . . . . ? C5B C6B C7B C8B 5.3(11) . . . . ? S2B C6B C7B C8B -178.8(5) . . . . ? C6B C7B C8B C9B -1.1(12) . . . . ? C7B C8B C9B C1B 177.8(6) . . . . ? C7B C8B C9B C10B -3.1(11) . . . . ? C2B C1B C9B C8B -179.9(6) . . . . ? C11B C1B C9B C8B -2.5(12) . . . . ? C2B C1B C9B C10B 0.8(7) . . . . ? C11B C1B C9B C10B 178.2(7) . . . . ? C5B C4B C10B C3B -176.8(7) . . . . ? C5B C4B C10B C9B 4.1(12) . . . . ? C2B C3B C10B C4B 178.6(6) . . . . ? C14B C3B C10B C4B -1.6(11) . . . . ? C2B C3B C10B C9B -2.1(7) . . . . ? C14B C3B C10B C9B 177.6(6) . . . . ? C8B C9B C10B C4B 0.7(11) . . . . ? C1B C9B C10B C4B -180.0(6) . . . . ? C8B C9B C10B C3B -178.5(6) . . . . ? C1B C9B C10B C3B 0.8(7) . . . . ? C12B O2B C11B O1B -1.8(10) . . . . ? C12B O2B C11B C1B 179.1(6) . . . . ? C9B C1B C11B O1B -180.0(7) . . . . ? C2B C1B C11B O1B -3.0(12) . . . . ? C9B C1B C11B O2B -0.9(11) . . . . ? C2B C1B C11B O2B 176.1(6) . . . . ? C11B O2B C12B C13B 179.3(6) . . . . ? C15B O4B C14B O3B 4.0(10) . . . . ? C15B O4B C14B C3B -174.7(6) . . . . ? C2B C3B C14B O3B -169.3(7) . . . . ? C10B C3B C14B O3B 11.1(11) . . . . ? C2B C3B C14B O4B 9.5(10) . . . . ? C10B C3B C14B O4B -170.2(6) . . . . ? C14B O4B C15B C16B -178.0(6) . . . . ? C29B P1B C17B C22B -18.8(7) . . . . ? C23B P1B C17B C22B 92.6(6) . . . . ? Au1B P1B C17B C22B -144.4(5) . . . . ? C29B P1B C17B C18B 162.5(5) . . . . ? C23B P1B C17B C18B -86.2(6) . . . . ? Au1B P1B C17B C18B 36.8(6) . . . . ? C22B C17B C18B C19B -1.7(10) . . . . ? P1B C17B C18B C19B 177.1(5) . . . . ? C17B C18B C19B C20B 0.9(11) . . . . ? C18B C19B C20B C21B -0.1(12) . . . . ? C19B C20B C21B C22B 0.2(12) . . . . ? C18B C17B C22B C21B 1.8(11) . . . . ? P1B C17B C22B C21B -177.0(6) . . . . ? C20B C21B C22B C17B -1.0(12) . . . . ? C17B P1B C23B C28B -7.5(7) . . . . ? C29B P1B C23B C28B 103.7(6) . . . . ? Au1B P1B C23B C28B -131.3(5) . . . . ? C17B P1B C23B C24B 173.5(5) . . . . ? C29B P1B C23B C24B -75.3(6) . . . . ? Au1B P1B C23B C24B 49.7(6) . . . . ? C28B C23B C24B C25B -2.7(10) . . . . ? P1B C23B C24B C25B 176.3(5) . . . . ? C23B C24B C25B C26B 3.8(10) . . . . ? C24B C25B C26B C27B -2.0(11) . . . . ? C25B C26B C27B C28B -0.9(11) . . . . ? C26B C27B C28B C23B 2.0(10) . . . . ? C24B C23B C28B C27B -0.2(10) . . . . ? P1B C23B C28B C27B -179.2(5) . . . . ? C17B P1B C29B C30B -63.8(7) . . . . ? C23B P1B C29B C30B -174.7(6) . . . . ? Au1B P1B C29B C30B 61.5(7) . . . . ? C17B P1B C29B C34B 121.0(6) . . . . ? C23B P1B C29B C34B 10.0(7) . . . . ? Au1B P1B C29B C34B -113.8(6) . . . . ? C34B C29B C30B C31B -4.3(12) . . . . ? P1B C29B C30B C31B -179.8(7) . . . . ? C29B C30B C31B C32B 3.7(13) . . . . ? C30B C31B C32B C33B -1.1(13) . . . . ? C31B C32B C33B C34B -0.7(12) . . . . ? C32B C33B C34B C29B 0.1(12) . . . . ? C30B C29B C34B C33B 2.4(11) . . . . ? P1B C29B C34B C33B 177.7(6) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A S1A H1A O1A 1.20(8) 2.01(8) 3.029(6) 140(5) . S1B H1B O1B 1.15(8) 2.13(8) 3.041(6) 134(5) . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.203 _refine_diff_density_min -0.548 _refine_diff_density_rms 0.103 _iucr_refine_instruction_details ; TITL 12027 in Pca2(1) CELL 0.71073 23.574 11.1504 23.342 90.000 90.000 90.000 ZERR 8.00 0.002 0.0010 0.002 0.000 0.000 0.000 LATT -1 SYMM -X, -Y, 0.5+Z SYMM 0.5+X, -Y, Z SYMM 0.5-X, Y, 0.5+Z SFAC C H O P S AU UNIT 272 240 32 8 16 8 TEMP -173 SIZE 0.12 0.30 0.32 omit -2 51.0 acta 50.5 conf wpdb -2 htab s1a o1a htab s1b o1b htab L.S. 4 BOND $h FMAP 2 PLAN 20 twin WGHT 0.032000 11.400000 BASF 0.24025 FVAR 0.10921 AU1A 6 0.511393 0.226325 0.546817 11.00000 0.01425 0.01741 = 0.01504 -0.00006 0.00060 -0.00208 S1A 5 0.757862 0.909998 0.475787 11.00000 0.02698 0.01843 = 0.02999 -0.00133 0.00736 -0.00565 H1A 2 0.761788 0.919720 0.526711 11.00000 -1.20000 S2A 5 0.558486 0.243234 0.459969 11.00000 0.01784 0.02083 = 0.01507 -0.00142 0.00080 -0.00463 P1A 4 0.463452 0.212027 0.630657 11.00000 0.01361 0.01565 = 0.01536 0.00050 0.00093 0.00086 O1A 3 0.740250 0.830946 0.598664 11.00000 0.02332 0.02144 = 0.02603 -0.00088 -0.00524 -0.01110 O2A 3 0.697562 0.660731 0.621553 11.00000 0.02468 0.02406 = 0.02078 -0.00187 -0.00414 -0.00709 O3A 3 0.719837 0.671329 0.326191 11.00000 0.04544 0.02496 = 0.02912 -0.00124 0.01468 -0.00832 O4A 3 0.737816 0.855124 0.360317 11.00000 0.03604 0.02417 = 0.01926 0.00469 0.00707 -0.00956 C1A 1 0.702973 0.707937 0.523911 11.00000 0.01030 0.01564 = 0.02076 -0.00176 -0.00008 -0.00309 C2A 1 0.720600 0.773752 0.475958 11.00000 0.01408 0.01718 = 0.02560 -0.00306 0.00573 0.00473 C3A 1 0.704390 0.711578 0.425587 11.00000 0.02493 0.01920 = 0.01870 0.00400 0.00047 0.00732 C4A 1 0.649760 0.525909 0.404322 11.00000 0.02149 0.02113 = 0.01477 -0.00052 0.00507 0.00389 AFIX 43 H4A 2 0.657022 0.541037 0.364947 11.00000 -1.20000 AFIX 0 C5A 1 0.617247 0.426570 0.415003 11.00000 0.01545 0.02431 = 0.01850 -0.00479 -0.00276 0.00237 AFIX 43 H5A 2 0.603926 0.386313 0.381752 11.00000 -1.20000 AFIX 0 C6A 1 0.600353 0.374396 0.467202 11.00000 0.01449 0.01984 = 0.01596 0.00788 -0.00122 -0.00006 C7A 1 0.616579 0.415586 0.520922 11.00000 0.02483 0.01714 = 0.01660 0.00339 -0.00030 -0.00248 AFIX 43 H7A 2 0.604352 0.367311 0.552101 11.00000 -1.20000 AFIX 0 C8A 1 0.647307 0.514429 0.536023 11.00000 0.01273 0.02716 = 0.01362 0.00132 -0.00428 -0.00224 AFIX 43 H8A 2 0.652022 0.523861 0.576190 11.00000 -1.20000 AFIX 0 C9A 1 0.673136 0.604370 0.503456 11.00000 0.01572 0.01846 = 0.01939 0.00391 0.00207 0.00712 C10A 1 0.673686 0.607652 0.441732 11.00000 0.01170 0.02215 = 0.02137 -0.00071 -0.00056 0.00722 C11A 1 0.715798 0.740550 0.582279 11.00000 0.00686 0.01459 = 0.04533 0.00776 -0.00103 -0.00330 C12A 1 0.710496 0.685998 0.682103 11.00000 0.02592 0.03073 = 0.01718 -0.00909 -0.00899 0.00076 AFIX 23 H12A 2 0.692406 0.762032 0.694179 11.00000 -1.20000 H12B 2 0.751979 0.693133 0.687761 11.00000 -1.20000 AFIX 0 C13A 1 0.687369 0.582582 0.716487 11.00000 0.02819 0.02075 = 0.02535 -0.00073 -0.00527 -0.00277 AFIX 137 H13A 2 0.646021 0.579636 0.712376 11.00000 -1.50000 H13B 2 0.697184 0.593445 0.756953 11.00000 -1.50000 H13C 2 0.703864 0.507416 0.702491 11.00000 -1.50000 AFIX 0 C14A 1 0.720481 0.741651 0.366048 11.00000 0.02449 0.01942 = 0.02664 0.00429 0.00297 -0.00345 C15A 1 0.760546 0.888016 0.304939 11.00000 0.03410 0.03536 = 0.02771 0.00598 0.00318 -0.01566 AFIX 23 H15A 2 0.785850 0.823270 0.291185 11.00000 -1.20000 H15B 2 0.783557 0.961798 0.309001 11.00000 -1.20000 AFIX 0 C16A 1 0.714802 0.909166 0.261407 11.00000 0.04648 0.03065 = 0.03435 -0.00560 0.01403 0.01116 AFIX 137 H16A 2 0.686498 0.964397 0.277202 11.00000 -1.50000 H16B 2 0.696562 0.832778 0.251823 11.00000 -1.50000 H16C 2 0.731465 0.944137 0.226760 11.00000 -1.50000 AFIX 0 C17A 1 0.510777 0.219166 0.692854 11.00000 0.01367 0.01906 = 0.02154 -0.00124 0.00346 0.00294 C18A 1 0.556949 0.297438 0.689957 11.00000 0.02717 0.00809 = 0.02213 0.00263 -0.00508 0.00231 AFIX 43 H18A 2 0.564494 0.340136 0.655572 11.00000 -1.20000 AFIX 0 C19A 1 0.591513 0.312709 0.736907 11.00000 0.02027 0.01964 = 0.02715 -0.00398 -0.00052 0.00031 AFIX 43 H19A 2 0.622488 0.367100 0.735262 11.00000 -1.20000 AFIX 0 C20A 1 0.581162 0.249650 0.785663 11.00000 0.02423 0.03893 = 0.01803 -0.00011 -0.00449 0.00443 AFIX 43 H20A 2 0.605065 0.260141 0.818043 11.00000 -1.20000 AFIX 0 C21A 1 0.536565 0.171139 0.788484 11.00000 0.02104 0.04240 = 0.02448 0.01004 -0.00166 0.00187 AFIX 43 H21A 2 0.530488 0.126210 0.822515 11.00000 -1.20000 AFIX 0 C22A 1 0.500450 0.156432 0.742731 11.00000 0.01679 0.04355 = 0.02717 0.00642 0.00571 -0.00474 AFIX 43 H22A 2 0.468857 0.103844 0.745433 11.00000 -1.20000 AFIX 0 C23A 1 0.412190 0.332809 0.641580 11.00000 0.01471 0.01156 = 0.02681 -0.00607 -0.00108 -0.00473 C24A 1 0.395285 0.403336 0.596398 11.00000 0.02525 0.03384 = 0.01977 0.00846 0.00786 0.00709 AFIX 43 H24A 2 0.410832 0.390937 0.559320 11.00000 -1.20000 AFIX 0 C25A 1 0.355270 0.492922 0.605379 11.00000 0.03699 0.04484 = 0.02385 0.02188 -0.00143 0.01293 AFIX 43 H25A 2 0.343203 0.541460 0.574230 11.00000 -1.20000 AFIX 0 C26A 1 0.333093 0.511650 0.659011 11.00000 0.02464 0.01481 = 0.03051 -0.00412 0.00344 0.00328 AFIX 43 H26A 2 0.305869 0.573374 0.664587 11.00000 -1.20000 AFIX 0 C27A 1 0.349598 0.442785 0.704541 11.00000 0.01974 0.03463 = 0.02442 -0.00933 -0.00137 -0.00029 AFIX 43 H27A 2 0.333776 0.456329 0.741409 11.00000 -1.20000 AFIX 0 C28A 1 0.389611 0.352970 0.696562 11.00000 0.02165 0.02430 = 0.01635 0.00669 -0.00167 0.00227 AFIX 43 H28A 2 0.401685 0.305379 0.728041 11.00000 -1.20000 AFIX 0 C29A 1 0.423004 0.074806 0.638735 11.00000 0.01723 0.01712 = 0.01133 -0.00120 0.00289 -0.00247 C30A 1 0.450359 -0.031734 0.650914 11.00000 0.01031 0.03085 = 0.02631 0.00413 0.00125 0.00690 AFIX 43 H30A 2 0.490266 -0.032254 0.656565 11.00000 -1.20000 AFIX 0 C31A 1 0.420042 -0.137852 0.654953 11.00000 0.02053 0.02206 = 0.02559 0.00413 0.00205 0.00438 AFIX 43 H31A 2 0.438863 -0.210944 0.663670 11.00000 -1.20000 AFIX 0 C32A 1 0.361895 -0.136022 0.646112 11.00000 0.02002 0.02092 = 0.01671 -0.00281 0.00762 -0.00744 AFIX 43 H32A 2 0.340839 -0.208422 0.648950 11.00000 -1.20000 AFIX 0 C33A 1 0.334526 -0.031522 0.633384 11.00000 0.01816 0.02653 = 0.01108 -0.00304 0.00125 0.00228 AFIX 43 H33A 2 0.294737 -0.031864 0.626931 11.00000 -1.20000 AFIX 0 C34A 1 0.364415 0.074684 0.629845 11.00000 0.01888 0.01008 = 0.01938 -0.00084 -0.00470 0.00466 AFIX 43 H34A 2 0.345196 0.147448 0.621390 11.00000 -1.20000 AFIX 0 AU1B 6 0.257865 0.723265 0.539559 11.00000 0.01356 0.01711 = 0.01619 -0.00022 0.00144 0.00172 S1B 5 0.014747 1.403951 0.628090 11.00000 0.02892 0.01778 = 0.02583 0.00004 -0.00070 0.00492 H1B 2 0.019457 1.427652 0.580494 11.00000 -1.20000 S2B 5 0.213613 0.734281 0.628139 11.00000 0.01768 0.01924 = 0.01710 0.00268 0.00154 0.00366 P1B 4 0.306062 0.718448 0.455873 11.00000 0.01438 0.01653 = 0.01811 -0.00203 0.00194 0.00052 O1B 3 0.023146 1.324365 0.503780 11.00000 0.02547 0.03118 = 0.02658 0.00069 -0.00529 0.00302 O2B 3 0.070282 1.160370 0.477003 11.00000 0.02873 0.02247 = 0.01881 -0.00314 -0.00151 0.00621 O3B 3 0.091029 1.199114 0.775498 11.00000 0.04212 0.02607 = 0.02262 -0.00618 -0.00109 0.01186 O4B 3 0.029837 1.334719 0.741169 11.00000 0.02863 0.03085 = 0.02155 -0.00211 0.00157 0.01170 C1B 1 0.065183 1.199570 0.575612 11.00000 0.01144 0.01708 = 0.02298 -0.00702 -0.00083 -0.00488 C2B 1 0.052063 1.267762 0.626000 11.00000 0.01690 0.01534 = 0.02385 -0.00259 -0.00154 -0.00569 C3B 1 0.072795 1.207730 0.674956 11.00000 0.01204 0.01974 = 0.02058 0.00071 0.00091 -0.00639 C4B 1 0.129812 1.019270 0.691758 11.00000 0.01931 0.02245 = 0.00790 -0.00054 -0.00576 -0.00620 AFIX 43 H4B 2 0.126596 1.034919 0.731633 11.00000 -1.20000 AFIX 0 C5B 1 0.160530 0.920283 0.678224 11.00000 0.01557 0.01908 = 0.01061 0.00234 -0.00501 0.00356 AFIX 43 H5B 2 0.177032 0.880574 0.710143 11.00000 -1.20000 AFIX 0 C6B 1 0.171913 0.867304 0.625777 11.00000 0.00960 0.01717 = 0.01896 0.00212 0.00050 -0.00651 C7B 1 0.150822 0.905715 0.573255 11.00000 0.01575 0.02078 = 0.01364 -0.00474 0.00045 -0.00188 AFIX 43 H7B 2 0.160063 0.855201 0.541837 11.00000 -1.20000 AFIX 0 C8B 1 0.118450 1.005729 0.558979 11.00000 0.01637 0.02190 = 0.01858 0.00102 -0.00462 -0.00239 AFIX 43 H8B 2 0.109768 1.013180 0.519396 11.00000 -1.20000 AFIX 0 C9B 1 0.096718 1.096849 0.593654 11.00000 0.01690 0.01375 = 0.01838 -0.00023 0.00082 -0.00105 C10B 1 0.101849 1.102779 0.656026 11.00000 0.01462 0.01191 = 0.02852 -0.00029 -0.00479 -0.00010 C11B 1 0.050393 1.235195 0.518020 11.00000 0.02391 0.00965 = 0.04611 -0.00339 -0.00519 0.00303 C12B 1 0.056734 1.188322 0.418597 11.00000 0.01701 0.02283 = 0.01223 0.00844 -0.00457 0.00389 AFIX 23 H12C 2 0.071594 1.268462 0.408202 11.00000 -1.20000 H12D 2 0.015137 1.187985 0.412770 11.00000 -1.20000 AFIX 0 C13B 1 0.084285 1.093050 0.382892 11.00000 0.03182 0.03769 = 0.02084 -0.00329 -0.01311 0.00365 AFIX 137 H13D 2 0.125274 1.093218 0.389891 11.00000 -1.50000 H13E 2 0.077017 1.109055 0.342267 11.00000 -1.50000 H13F 2 0.068583 1.014564 0.393164 11.00000 -1.50000 AFIX 0 C14B 1 0.066442 1.242930 0.734776 11.00000 0.01792 0.02252 = 0.02561 0.00111 0.00337 0.00142 C15B 1 0.023783 1.384647 0.798271 11.00000 0.03365 0.03241 = 0.02097 -0.00622 0.00536 0.00262 AFIX 23 H15C 2 0.060298 1.418562 0.811553 11.00000 -1.20000 H15D 2 0.011683 1.321771 0.825609 11.00000 -1.20000 AFIX 0 C16B 1 -0.020370 1.481212 0.794252 11.00000 0.03503 0.03165 = 0.03268 0.00360 0.01722 0.01106 AFIX 137 H16D 2 -0.055222 1.447818 0.777844 11.00000 -1.50000 H16E 2 -0.006410 1.546089 0.769687 11.00000 -1.50000 H16F 2 -0.028313 1.512798 0.832602 11.00000 -1.50000 AFIX 0 C17B 1 0.260706 0.727616 0.393181 11.00000 0.01523 0.01366 = 0.02068 -0.00142 0.00111 -0.00889 C18B 1 0.212714 0.801490 0.395730 11.00000 0.02197 0.01957 = 0.02013 -0.00516 0.00465 0.00137 AFIX 43 H18B 2 0.203785 0.842165 0.430336 11.00000 -1.20000 AFIX 0 C19B 1 0.178558 0.815569 0.348757 11.00000 0.02508 0.02284 = 0.02328 0.00212 0.00126 0.00710 AFIX 43 H19B 2 0.146433 0.866819 0.350862 11.00000 -1.20000 AFIX 0 C20B 1 0.190433 0.755970 0.298471 11.00000 0.03326 0.02890 = 0.02830 0.00691 -0.00380 -0.00024 AFIX 43 H20B 2 0.166548 0.765953 0.266040 11.00000 -1.20000 AFIX 0 C21B 1 0.237876 0.680574 0.295345 11.00000 0.03398 0.03562 = 0.03140 -0.01008 0.00524 0.00224 AFIX 43 H21B 2 0.246443 0.639308 0.260805 11.00000 -1.20000 AFIX 0 C22B 1 0.272168 0.666750 0.343059 11.00000 0.02108 0.02854 = 0.01744 -0.00437 0.00099 -0.00283 AFIX 43 H22B 2 0.304006 0.614659 0.341246 11.00000 -1.20000 AFIX 0 C23B 1 0.355257 0.843766 0.448891 11.00000 0.01537 0.00891 = 0.01958 -0.00045 0.00700 0.00253 C24B 1 0.392138 0.867943 0.494117 11.00000 0.02906 0.01750 = 0.01958 -0.00396 0.00068 -0.00525 AFIX 43 H24B 2 0.389729 0.822522 0.528464 11.00000 -1.20000 AFIX 0 C25B 1 0.432555 0.958624 0.489072 11.00000 0.01670 0.02547 = 0.02436 -0.00282 -0.00164 -0.00511 AFIX 43 H25B 2 0.459202 0.972057 0.518922 11.00000 -1.20000 AFIX 0 C26B 1 0.433491 1.026471 0.441898 11.00000 0.02081 0.01730 = 0.03387 -0.01508 0.00008 -0.00470 AFIX 43 H26B 2 0.460369 1.089716 0.439288 11.00000 -1.20000 AFIX 0 C27B 1 0.395891 1.007190 0.395920 11.00000 0.02264 0.02313 = 0.02859 0.00242 0.00201 0.00300 AFIX 43 H27B 2 0.396740 1.056903 0.362879 11.00000 -1.20000 AFIX 0 C28B 1 0.357936 0.914119 0.400413 11.00000 0.01912 0.02050 = 0.02676 -0.00536 -0.00072 0.00340 AFIX 43 H28B 2 0.332983 0.897905 0.369408 11.00000 -1.20000 AFIX 0 C29B 1 0.348531 0.584219 0.445798 11.00000 0.01036 0.02281 = 0.01626 -0.00587 0.00220 -0.00073 C30B 1 0.321441 0.472975 0.444060 11.00000 0.01421 0.02160 = 0.03661 -0.00303 0.00262 -0.00780 AFIX 43 H30B 2 0.281373 0.469087 0.447999 11.00000 -1.20000 AFIX 0 C31B 1 0.351755 0.369408 0.436766 11.00000 0.03287 0.01488 = 0.04539 -0.00556 -0.00224 -0.00144 AFIX 43 H31B 2 0.332589 0.294793 0.433407 11.00000 -1.20000 AFIX 0 C32B 1 0.411067 0.373625 0.434262 11.00000 0.02693 0.01570 = 0.02343 -0.00018 0.00362 0.00419 AFIX 43 H32B 2 0.432209 0.301671 0.429894 11.00000 -1.20000 AFIX 0 C33B 1 0.438905 0.482679 0.438151 11.00000 0.01720 0.02606 = 0.02457 -0.00012 0.00032 0.00047 AFIX 43 H33B 2 0.479156 0.485889 0.436918 11.00000 -1.20000 AFIX 0 C34B 1 0.407930 0.585743 0.443785 11.00000 0.01779 0.02227 = 0.02047 0.00282 0.00329 -0.00296 AFIX 43 H34B 2 0.427209 0.660358 0.446404 11.00000 -1.20000 HKLF 4 REM 12027 in Pca2(1) REM R1 = 0.0294 for 9157 Fo > 4sig(Fo) and 0.0342 for all 10050 data REM 768 parameters refined using 1 restraints END WGHT 0.0162 11.3346 REM Highest difference peak 1.203, deepest hole -0.548, 1-sigma level 0.103 Q1 1 0.2596 0.6279 0.5394 11.00000 0.05 1.20 Q2 1 0.5099 0.1316 0.5480 11.00000 0.05 1.12 Q3 1 0.7404 0.7172 0.5485 11.00000 0.05 0.82 Q4 1 0.5101 0.2173 0.5869 11.00000 0.05 0.78 Q5 1 0.2377 0.7982 0.5321 11.00000 0.05 0.78 Q6 1 0.5131 0.2170 0.5033 11.00000 0.05 0.77 Q7 1 0.2390 0.7967 0.5457 11.00000 0.05 0.77 Q8 1 0.2447 0.7165 0.5787 11.00000 0.05 0.69 Q9 1 0.5276 0.3023 0.5433 11.00000 0.05 0.66 Q10 1 0.2890 0.6773 0.5592 11.00000 0.05 0.66 Q11 1 0.2560 0.7179 0.4992 11.00000 0.05 0.65 Q12 1 0.2369 0.6968 0.5063 11.00000 0.05 0.64 Q13 1 0.2789 0.7935 0.5492 11.00000 0.05 0.63 Q14 1 0.2286 0.7123 0.5649 11.00000 0.05 0.62 Q15 1 0.4944 0.3017 0.5325 11.00000 0.05 0.60 Q16 1 0.5417 0.1819 0.5255 11.00000 0.05 0.58 Q17 1 0.4913 0.3005 0.5617 11.00000 0.05 0.56 Q18 1 0.0305 1.2128 0.5478 11.00000 0.05 0.55 Q19 1 0.7945 0.7155 0.5389 11.00000 0.05 0.50 Q20 1 0.4423 0.2900 0.6392 11.00000 0.05 0.49 ; #===END _database_code_depnum_ccdc_archive 'CCDC 941159'