# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2002 data_bf_m _database_code_CSD 189550 _journal_coden_Cambridge 207 loop_ _publ_author_name 'Perlmutter, Patrick' 'Fraser, Benjamin' _publ_contact_author_name 'Dr Patrick Perlmutter' _publ_contact_author_address ; Department of Chemistry Monash University PO Box 23 Melbourne Victoria 3800 AUSTRALIA ; _publ_contact_author_email 'PATRICK.PERLMUTTER@SCI.MONASH.EDU.AU' _publ_requested_journal 'Perkin Transactions 1' _publ_section_title ; A Nucleophilic Addition Ring Closure [NARC]-Based Synthesis of (+) -Nonactic acid ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H50 Cl1 Hg1 N1 O5 S1 Si1' _chemical_formula_structural 'C36 H50 CL1 HG1 N1 O5 S1 SI1' _chemical_formula_sum 'C36 H50 Cl1 Hg1 N1 O5 S1 Si1' _chemical_formula_weight 872.96 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Hg' 'Hg' -2.3894 9.2266 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Si' 'Si' 0.0817 0.0704 '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 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 7.5515(1) _cell_length_b 19.0540(1) _cell_length_c 25.3617(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 3649.20(6) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 38127 _cell_measurement_theta_min 2.9 _cell_measurement_theta_max 28.3 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.589 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1760 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 0 0 0.1190 -1 0 0 0.1190 0 1 0 0.0690 0 -1 0 0.0690 0 0 1 0.0440 0 0 -1 0.0440 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; PLATON Reference : Spek, A.L. (1990), Acta Cryst. A46, C-34 a grid of 8 x 8 x 8 = 512 sampling points was used ; _exptl_absorpt_correction_T_min 0.4556 _exptl_absorpt_correction_T_max 0.6885 _exptl_absorpt_correction_T_ave 0.6342 _exptl_absorpt_coefficient_mu 4.423 _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_radiation_probe x-ray _diffrn_source 'Enraf Nonius FR590' _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_UB_11 -0.104717 _diffrn_orient_matrix_UB_12 0.323086E-1 _diffrn_orient_matrix_UB_13 0.743408E-1 _diffrn_orient_matrix_UB_21 -0.303809E-1 _diffrn_orient_matrix_UB_22 0 _diffrn_orient_matrix_UB_23 -0.427949E-1 _diffrn_orient_matrix_UB_31 -0.78442E-2 _diffrn_orient_matrix_UB_32 -0.38238E-1 _diffrn_orient_matrix_UB_33 0.55688E-2 _diffrn_reflns_number 38911 _diffrn_reflns_av_R_equivalents 0.0437 _diffrn_reflns_av_sigmaI/netI 0.0363 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 2.90 _diffrn_reflns_theta_max 28.29 _reflns_number_total 8889 _reflns_number_gt 8488 _reflns_threshold_expression >2sigma(I) _chemical_compound_source 'synthesis as described' _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R- factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R- factors(gt) etc. and is not relevant to the choice of reflections for refinement. R- factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0158P)^2^+0.9320P] 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 0.003(3) _refine_ls_number_reflns 8889 _refine_ls_number_parameters 422 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0242 _refine_ls_R_factor_gt 0.0217 _refine_ls_wR_factor_ref 0.0450 _refine_ls_wR_factor_gt 0.0444 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.0294(4) 0.39098(15) 0.41400(10) 0.0187(6) Uani 1 1 d . . . C2 C -0.0438(4) 0.31186(15) 0.41145(10) 0.0188(6) Uani 1 1 d . . . H2 H 0.0736 0.2914 0.4016 0.023 Uiso 1 1 calc R . . C3 C -0.1794(4) 0.29558(14) 0.36843(10) 0.0164(6) Uani 1 1 d . . . H3 H -0.2964 0.3159 0.3788 0.020 Uiso 1 1 calc R . . C4 C -0.2040(4) 0.21751(15) 0.35516(10) 0.0219(6) Uani 1 1 d . . . H4A H -0.3084 0.1978 0.3736 0.026 Uiso 1 1 calc R . . H4B H -0.0977 0.1900 0.3650 0.026 Uiso 1 1 calc R . . C5 C -0.2316(4) 0.21743(15) 0.29492(10) 0.0211(6) Uani 1 1 d . . . H5A H -0.1357 0.1913 0.2770 0.025 Uiso 1 1 calc R . . H5B H -0.3468 0.1960 0.2855 0.025 Uiso 1 1 calc R . . C6 C -0.2274(3) 0.29542(13) 0.27980(10) 0.0174(5) Uani 1 1 d . . . H6 H -0.3504 0.3145 0.2821 0.021 Uiso 1 1 calc R . . C7 C -0.1529(3) 0.31220(13) 0.22567(10) 0.0164(6) Uani 1 1 d . . . H7 H -0.2232 0.2842 0.1997 0.020 Uiso 1 1 calc R . . C8 C -0.1705(3) 0.38942(13) 0.20916(10) 0.0161(5) Uani 1 1 d . . . H8 H -0.1428 0.4195 0.2404 0.019 Uiso 1 1 calc R . . C9 C -0.3583(4) 0.40548(14) 0.19148(11) 0.0211(6) Uani 1 1 d . . . H9A H -0.3862 0.3778 0.1600 0.032 Uiso 1 1 calc R . . H9B H -0.3685 0.4556 0.1832 0.032 Uiso 1 1 calc R . . H9C H -0.4412 0.3935 0.2198 0.032 Uiso 1 1 calc R . . C10 C -0.1022(4) 0.28283(17) 0.46493(10) 0.0307(6) Uani 1 1 d . . . H10A H -0.2171 0.3031 0.4745 0.046 Uiso 1 1 calc R . . H10B H -0.0142 0.2952 0.4918 0.046 Uiso 1 1 calc R . . H10C H -0.1128 0.2316 0.4628 0.046 Uiso 1 1 calc R . . C11 C 0.1361(4) 0.49896(13) 0.39211(10) 0.0166(6) Uani 1 1 d . . . H11 H 0.1161 0.5215 0.4272 0.020 Uiso 1 1 calc R . . C12 C 0.3229(4) 0.51639(14) 0.37160(10) 0.0179(6) Uani 1 1 d . . . C13 C 0.3546(4) 0.59389(14) 0.38622(11) 0.0246(7) Uani 1 1 d . . . H13A H 0.4780 0.6082 0.3786 0.030 Uiso 1 1 calc R . . H13B H 0.3283 0.6027 0.4239 0.030 Uiso 1 1 calc R . . C14 C 0.2206(4) 0.63271(16) 0.34954(12) 0.0289(7) Uani 1 1 d . . . H14A H 0.1278 0.6567 0.3704 0.035 Uiso 1 1 calc R . . H14B H 0.2817 0.6677 0.3271 0.035 Uiso 1 1 calc R . . C15 C 0.1404(4) 0.57304(14) 0.31576(11) 0.0237(7) Uani 1 1 d . . . H15 H 0.0899 0.5891 0.2814 0.028 Uiso 1 1 calc R . . C16 C 0.0102(4) 0.53157(15) 0.35003(11) 0.0207(6) Uani 1 1 d . . . H16A H -0.0512 0.4948 0.3294 0.025 Uiso 1 1 calc R . . H16B H -0.0789 0.5628 0.3665 0.025 Uiso 1 1 calc R . . C17 C 0.4515(4) 0.46274(14) 0.39344(12) 0.0223(6) Uani 1 1 d . . . H17A H 0.5016 0.4792 0.4273 0.027 Uiso 1 1 calc R . . H17B H 0.5498 0.4548 0.3683 0.027 Uiso 1 1 calc R . . C18 C 0.2964(4) 0.52102(15) 0.31015(11) 0.0213(6) Uani 1 1 d . . . C19 C 0.4588(4) 0.55062(16) 0.28129(13) 0.0304(7) Uani 1 1 d . . . H19A H 0.4359 0.5513 0.2433 0.046 Uiso 1 1 calc R . . H19B H 0.5620 0.5210 0.2886 0.046 Uiso 1 1 calc R . . H19C H 0.4821 0.5985 0.2936 0.046 Uiso 1 1 calc R . . C20 C 0.2442(4) 0.45284(15) 0.28224(12) 0.0248(6) Uani 1 1 d . . . H20A H 0.3467 0.4214 0.2808 0.037 Uiso 1 1 calc R . . H20B H 0.2044 0.4635 0.2463 0.037 Uiso 1 1 calc R . . H20C H 0.1480 0.4301 0.3017 0.037 Uiso 1 1 calc R . . C21 C -0.1449(4) 0.53926(14) 0.12865(10) 0.0186(6) Uani 1 1 d . . . C22 C -0.1414(4) 0.56118(13) 0.18115(10) 0.0196(6) Uani 1 1 d . . . H22 H -0.0885 0.5315 0.2068 0.023 Uiso 1 1 calc R . . C23 C -0.2124(4) 0.62470(15) 0.19701(12) 0.0240(6) Uani 1 1 d . . . H23 H -0.2110 0.6374 0.2332 0.029 Uiso 1 1 calc R . . C24 C -0.2856(4) 0.66982(15) 0.16015(13) 0.0275(7) Uani 1 1 d . . . H24 H -0.3341 0.7136 0.1708 0.033 Uiso 1 1 calc R . . C25 C -0.2870(4) 0.65044(17) 0.10802(13) 0.0302(7) Uani 1 1 d . . . H25 H -0.3352 0.6816 0.0825 0.036 Uiso 1 1 calc R . . C26 C -0.2189(4) 0.58581(15) 0.09176(12) 0.0259(7) Uani 1 1 d . . . H26 H -0.2228 0.5732 0.0555 0.031 Uiso 1 1 calc R . . C27 C -0.1754(4) 0.39823(15) 0.06309(10) 0.0207(6) Uani 1 1 d . . . C28 C -0.2371(4) 0.42605(18) 0.01541(12) 0.0308(7) Uani 1 1 d . . . H28 H -0.2246 0.4749 0.0089 0.037 Uiso 1 1 calc R . . C29 C -0.3157(5) 0.3840(2) -0.02234(13) 0.0432(9) Uani 1 1 d . . . H29 H -0.3550 0.4041 -0.0545 0.052 Uiso 1 1 calc R . . C30 C -0.3377(5) 0.3125(2) -0.01360(14) 0.0461(10) Uani 1 1 d . . . H30 H -0.3911 0.2837 -0.0397 0.055 Uiso 1 1 calc R . . C31 C -0.2814(5) 0.2837(2) 0.03319(13) 0.0446(9) Uani 1 1 d . . . H31 H -0.2980 0.2351 0.0399 0.054 Uiso 1 1 calc R . . C32 C -0.2001(5) 0.32618(17) 0.07072(12) 0.0323(8) Uani 1 1 d . . . H32 H -0.1598 0.3055 0.1026 0.039 Uiso 1 1 calc R . . C33 C 0.1879(4) 0.45958(15) 0.09005(10) 0.0205(6) Uani 1 1 d . . . C34 C 0.1905(5) 0.4988(2) 0.03692(12) 0.0364(9) Uani 1 1 d . . . H34A H 0.1295 0.4706 0.0102 0.055 Uiso 1 1 calc R . . H34B H 0.3134 0.5066 0.0260 0.055 Uiso 1 1 calc R . . H34C H 0.1304 0.5440 0.0408 0.055 Uiso 1 1 calc R . . C35 C 0.2951(4) 0.50336(18) 0.12979(12) 0.0284(7) Uani 1 1 d . . . H35A H 0.4158 0.5100 0.1165 0.043 Uiso 1 1 calc R . . H35B H 0.2993 0.4788 0.1637 0.043 Uiso 1 1 calc R . . H35C H 0.2384 0.5492 0.1345 0.043 Uiso 1 1 calc R . . C36 C 0.2736(4) 0.38757(17) 0.08317(14) 0.0340(8) Uani 1 1 d . . . H36A H 0.3940 0.3933 0.0694 0.051 Uiso 1 1 calc R . . H36B H 0.2035 0.3596 0.0584 0.051 Uiso 1 1 calc R . . H36C H 0.2785 0.3636 0.1173 0.051 Uiso 1 1 calc R . . Cl1 Cl 0.39395(11) 0.24284(4) 0.19851(3) 0.03220(17) Uani 1 1 d . . . Hg1 Hg 0.109958(13) 0.281463(5) 0.216939(4) 0.01876(3) Uani 1 1 d . . . N1 N 0.1270(3) 0.42207(11) 0.39696(8) 0.0159(4) Uani 1 1 d . . . O1 O -0.1530(3) 0.42845(11) 0.42681(8) 0.0258(5) Uani 1 1 d . . . O2 O -0.1214(3) 0.32798(9) 0.32016(6) 0.0183(4) Uani 1 1 d . . . O3 O -0.0405(2) 0.40364(10) 0.16864(7) 0.0163(4) Uani 1 1 d . . . O4 O 0.3574(3) 0.33571(10) 0.36027(9) 0.0308(5) Uani 1 1 d . . . O5 O 0.3471(3) 0.35710(11) 0.45539(8) 0.0324(5) Uani 1 1 d . . . S1 S 0.32791(10) 0.38365(4) 0.40297(3) 0.02082(15) Uani 1 1 d . . . Si1 Si -0.04928(10) 0.45013(4) 0.11347(3) 0.01617(16) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0192(15) 0.0258(15) 0.0110(12) 0.0021(11) -0.0004(11) 0.0028(12) C2 0.0196(15) 0.0190(13) 0.0177(13) 0.0046(11) 0.0011(11) 0.0013(11) C3 0.0156(13) 0.0170(14) 0.0166(12) 0.0046(10) 0.0035(10) 0.0006(11) C4 0.0260(16) 0.0178(13) 0.0218(13) 0.0078(12) 0.0009(11) -0.0038(13) C5 0.0229(14) 0.0180(13) 0.0225(13) 0.0009(11) -0.0006(10) -0.0063(12) C6 0.0187(13) 0.0166(13) 0.0169(12) 0.0019(11) -0.0022(11) -0.0008(10) C7 0.0185(15) 0.0124(11) 0.0182(13) 0.0000(9) -0.0014(10) 0.0019(10) C8 0.0164(13) 0.0167(12) 0.0153(13) 0.0007(10) 0.0021(10) 0.0043(10) C9 0.0180(17) 0.0189(13) 0.0265(14) 0.0042(11) 0.0003(12) 0.0029(12) C10 0.0370(17) 0.0338(16) 0.0213(13) 0.0092(12) -0.0013(13) -0.0032(19) C11 0.0200(16) 0.0148(12) 0.0151(12) -0.0008(9) -0.0011(11) 0.0032(11) C12 0.0220(15) 0.0143(13) 0.0173(12) -0.0006(10) -0.0010(11) -0.0003(11) C13 0.0319(19) 0.0167(13) 0.0252(14) -0.0022(11) -0.0017(12) -0.0018(13) C14 0.041(2) 0.0190(15) 0.0270(15) 0.0003(12) -0.0009(14) 0.0009(13) C15 0.0317(19) 0.0185(13) 0.0208(13) 0.0038(10) -0.0033(12) 0.0032(13) C16 0.0236(16) 0.0183(14) 0.0202(13) 0.0024(11) -0.0007(12) 0.0059(12) C17 0.0197(16) 0.0163(14) 0.0310(15) -0.0005(11) -0.0035(12) -0.0027(12) C18 0.0256(17) 0.0201(14) 0.0182(13) 0.0031(11) -0.0008(12) -0.0037(12) C19 0.0355(17) 0.0278(16) 0.0280(15) -0.0008(14) 0.0069(15) -0.0079(13) C20 0.0284(16) 0.0268(15) 0.0192(13) -0.0037(13) 0.0048(13) -0.0017(12) C21 0.0179(17) 0.0155(13) 0.0225(13) 0.0023(10) 0.0018(11) 0.0015(11) C22 0.0221(17) 0.0135(12) 0.0231(13) 0.0025(10) 0.0012(11) -0.0009(11) C23 0.0243(17) 0.0178(14) 0.0299(15) -0.0027(12) 0.0036(12) -0.0042(12) C24 0.0237(17) 0.0147(14) 0.0440(19) -0.0017(13) 0.0061(14) 0.0015(12) C25 0.0308(19) 0.0211(15) 0.0386(17) 0.0080(14) -0.0031(14) 0.0038(14) C26 0.0294(18) 0.0221(15) 0.0262(15) 0.0024(12) 0.0002(13) 0.0043(13) C27 0.0214(15) 0.0227(14) 0.0179(13) -0.0012(11) -0.0002(11) 0.0074(12) C28 0.035(2) 0.0344(18) 0.0225(15) -0.0002(13) -0.0092(13) 0.0089(15) C29 0.047(2) 0.055(2) 0.0270(17) -0.0062(16) -0.0168(16) 0.014(2) C30 0.053(3) 0.045(2) 0.0394(19) -0.0208(16) -0.0207(17) 0.0066(19) C31 0.063(3) 0.0266(17) 0.044(2) -0.0090(16) -0.0143(17) -0.0024(19) C32 0.043(2) 0.0263(17) 0.0272(16) -0.0022(13) -0.0056(14) 0.0020(15) C33 0.0181(15) 0.0263(15) 0.0171(13) 0.0047(11) -0.0002(11) 0.0030(12) C34 0.0260(18) 0.058(2) 0.0256(16) 0.0156(15) 0.0050(14) 0.0005(18) C35 0.0213(17) 0.0381(19) 0.0257(15) 0.0013(13) -0.0005(12) -0.0018(14) C36 0.0258(18) 0.0314(18) 0.045(2) -0.0012(15) 0.0084(15) 0.0064(14) Cl1 0.0195(4) 0.0253(3) 0.0518(4) 0.0104(3) 0.0060(4) 0.0065(3) Hg1 0.01696(5) 0.01545(5) 0.02387(5) 0.00387(4) 0.00095(4) 0.00295(4) N1 0.0159(12) 0.0138(10) 0.0181(10) 0.0013(8) 0.0031(9) 0.0020(9) O1 0.0230(12) 0.0257(11) 0.0288(11) -0.0010(8) 0.0051(9) 0.0054(9) O2 0.0213(10) 0.0178(9) 0.0158(8) 0.0037(7) -0.0019(8) -0.0038(9) O3 0.0156(10) 0.0180(10) 0.0153(9) 0.0045(7) 0.0021(7) 0.0030(8) O4 0.0213(12) 0.0183(10) 0.0528(13) -0.0110(9) 0.0084(10) 0.0007(9) O5 0.0307(13) 0.0275(11) 0.0391(12) 0.0151(9) -0.0103(10) -0.0008(10) S1 0.0172(4) 0.0144(3) 0.0309(4) 0.0015(3) -0.0020(3) 0.0025(3) Si1 0.0177(4) 0.0167(4) 0.0141(3) 0.0015(3) -0.0006(3) 0.0036(3) _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 C1 O1 1.219(3) . ? C1 N1 1.390(4) . ? C1 C2 1.513(4) . ? C2 C3 1.528(4) . ? C2 C10 1.530(4) . ? C2 H2 1.0000 . ? C3 O2 1.439(3) . ? C3 C4 1.536(4) . ? C3 H3 1.0000 . ? C4 C5 1.542(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.535(4) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 O2 1.440(3) . ? C6 C7 1.518(4) . ? C6 H6 1.0000 . ? C7 C8 1.536(3) . ? C7 Hg1 2.081(3) . ? C7 H7 1.0000 . ? C8 O3 1.447(3) . ? C8 C9 1.518(4) . ? C8 H8 1.0000 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 N1 1.472(3) . ? C11 C12 1.540(4) . ? C11 C16 1.559(4) . ? C11 H11 1.0000 . ? C12 C17 1.515(4) . ? C12 C13 1.541(4) . ? C12 C18 1.574(4) . ? C13 C14 1.561(4) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.547(4) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.532(4) . ? C15 C18 1.546(4) . ? C15 H15 1.0000 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 S1 1.789(3) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C20 1.531(4) . ? C18 C19 1.535(4) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C22 1.396(4) . ? C21 C26 1.405(4) . ? C21 Si1 1.885(3) . ? C22 C23 1.384(4) . ? C22 H22 0.9500 . ? C23 C24 1.385(4) . ? C23 H23 0.9500 . ? C24 C25 1.373(4) . ? C24 H24 0.9500 . ? C25 C26 1.397(4) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 C32 1.399(4) . ? C27 C28 1.400(4) . ? C27 Si1 1.876(3) . ? C28 C29 1.383(5) . ? C28 H28 0.9500 . ? C29 C30 1.390(5) . ? C29 H29 0.9500 . ? C30 C31 1.374(5) . ? C30 H30 0.9500 . ? C31 C32 1.392(4) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? C33 C36 1.527(4) . ? C33 C35 1.538(4) . ? C33 C34 1.541(4) . ? C33 Si1 1.896(3) . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? Cl1 Hg1 2.3150(8) . ? N1 S1 1.692(2) . ? O3 Si1 1.6573(19) . ? O4 S1 1.434(2) . ? O5 S1 1.430(2) . ? 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 O1 C1 N1 118.9(3) . . ? O1 C1 C2 122.7(3) . . ? N1 C1 C2 118.2(2) . . ? C1 C2 C3 106.3(2) . . ? C1 C2 C10 110.1(2) . . ? C3 C2 C10 111.5(2) . . ? C1 C2 H2 109.6 . . ? C3 C2 H2 109.6 . . ? C10 C2 H2 109.6 . . ? O2 C3 C2 108.4(2) . . ? O2 C3 C4 105.4(2) . . ? C2 C3 C4 115.7(2) . . ? O2 C3 H3 109.0 . . ? C2 C3 H3 109.0 . . ? C4 C3 H3 109.0 . . ? C3 C4 C5 103.6(2) . . ? C3 C4 H4A 111.1 . . ? C5 C4 H4A 111.1 . . ? C3 C4 H4B 111.1 . . ? C5 C4 H4B 111.1 . . ? H4A C4 H4B 109.0 . . ? C6 C5 C4 104.1(2) . . ? C6 C5 H5A 110.9 . . ? C4 C5 H5A 110.9 . . ? C6 C5 H5B 110.9 . . ? C4 C5 H5B 110.9 . . ? H5A C5 H5B 109.0 . . ? O2 C6 C7 110.3(2) . . ? O2 C6 C5 104.5(2) . . ? C7 C6 C5 115.9(2) . . ? O2 C6 H6 108.6 . . ? C7 C6 H6 108.6 . . ? C5 C6 H6 108.6 . . ? C6 C7 C8 114.6(2) . . ? C6 C7 Hg1 112.98(17) . . ? C8 C7 Hg1 108.86(17) . . ? C6 C7 H7 106.6 . . ? C8 C7 H7 106.6 . . ? Hg1 C7 H7 106.6 . . ? O3 C8 C9 112.7(2) . . ? O3 C8 C7 108.3(2) . . ? C9 C8 C7 110.8(2) . . ? O3 C8 H8 108.3 . . ? C9 C8 H8 108.3 . . ? C7 C8 H8 108.3 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C2 C10 H10A 109.5 . . ? C2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N1 C11 C12 106.6(2) . . ? N1 C11 C16 115.2(2) . . ? C12 C11 C16 104.0(2) . . ? N1 C11 H11 110.3 . . ? C12 C11 H11 110.3 . . ? C16 C11 H11 110.3 . . ? C17 C12 C11 108.5(2) . . ? C17 C12 C13 117.3(2) . . ? C11 C12 C13 105.5(2) . . ? C17 C12 C18 118.8(2) . . ? C11 C12 C18 103.3(2) . . ? C13 C12 C18 101.8(2) . . ? C12 C13 C14 102.1(2) . . ? C12 C13 H13A 111.3 . . ? C14 C13 H13A 111.3 . . ? C12 C13 H13B 111.3 . . ? C14 C13 H13B 111.3 . . ? H13A C13 H13B 109.2 . . ? C15 C14 C13 103.6(2) . . ? C15 C14 H14A 111.0 . . ? C13 C14 H14A 111.0 . . ? C15 C14 H14B 111.0 . . ? C13 C14 H14B 111.0 . . ? H14A C14 H14B 109.0 . . ? C16 C15 C18 102.2(2) . . ? C16 C15 C14 108.4(2) . . ? C18 C15 C14 103.0(2) . . ? C16 C15 H15 114.0 . . ? C18 C15 H15 114.0 . . ? C14 C15 H15 114.0 . . ? C15 C16 C11 101.7(2) . . ? C15 C16 H16A 111.4 . . ? C11 C16 H16A 111.4 . . ? C15 C16 H16B 111.4 . . ? C11 C16 H16B 111.4 . . ? H16A C16 H16B 109.3 . . ? C12 C17 S1 106.47(19) . . ? C12 C17 H17A 110.4 . . ? S1 C17 H17A 110.4 . . ? C12 C17 H17B 110.4 . . ? S1 C17 H17B 110.4 . . ? H17A C17 H17B 108.6 . . ? C20 C18 C19 107.3(2) . . ? C20 C18 C15 113.0(2) . . ? C19 C18 C15 114.6(2) . . ? C20 C18 C12 116.3(2) . . ? C19 C18 C12 113.0(2) . . ? C15 C18 C12 92.4(2) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C22 C21 C26 117.0(3) . . ? C22 C21 Si1 117.2(2) . . ? C26 C21 Si1 125.8(2) . . ? C23 C22 C21 122.1(3) . . ? C23 C22 H22 118.9 . . ? C21 C22 H22 118.9 . . ? C22 C23 C24 120.1(3) . . ? C22 C23 H23 120.0 . . ? C24 C23 H23 120.0 . . ? C25 C24 C23 119.1(3) . . ? C25 C24 H24 120.5 . . ? C23 C24 H24 120.5 . . ? C24 C25 C26 121.2(3) . . ? C24 C25 H25 119.4 . . ? C26 C25 H25 119.4 . . ? C25 C26 C21 120.4(3) . . ? C25 C26 H26 119.8 . . ? C21 C26 H26 119.8 . . ? C32 C27 C28 116.6(3) . . ? C32 C27 Si1 119.4(2) . . ? C28 C27 Si1 123.9(2) . . ? C29 C28 C27 121.4(3) . . ? C29 C28 H28 119.3 . . ? C27 C28 H28 119.3 . . ? C28 C29 C30 120.6(3) . . ? C28 C29 H29 119.7 . . ? C30 C29 H29 119.7 . . ? C31 C30 C29 119.4(3) . . ? C31 C30 H30 120.3 . . ? C29 C30 H30 120.3 . . ? C30 C31 C32 119.7(3) . . ? C30 C31 H31 120.1 . . ? C32 C31 H31 120.1 . . ? C31 C32 C27 122.3(3) . . ? C31 C32 H32 118.9 . . ? C27 C32 H32 118.9 . . ? C36 C33 C35 109.8(3) . . ? C36 C33 C34 109.3(3) . . ? C35 C33 C34 107.7(3) . . ? C36 C33 Si1 110.5(2) . . ? C35 C33 Si1 110.07(19) . . ? C34 C33 Si1 109.4(2) . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C33 C35 H35A 109.5 . . ? C33 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C33 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C33 C36 H36A 109.5 . . ? C33 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C33 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C7 Hg1 Cl1 173.93(7) . . ? C1 N1 C11 119.3(2) . . ? C1 N1 S1 123.34(18) . . ? C11 N1 S1 113.35(18) . . ? C3 O2 C6 104.51(19) . . ? C8 O3 Si1 132.26(16) . . ? O5 S1 O4 117.45(13) . . ? O5 S1 N1 109.12(12) . . ? O4 S1 N1 110.31(12) . . ? O5 S1 C17 111.77(13) . . ? O4 S1 C17 110.70(13) . . ? N1 S1 C17 95.23(12) . . ? O3 Si1 C27 108.28(12) . . ? O3 Si1 C21 108.93(11) . . ? C27 Si1 C21 114.81(13) . . ? O3 Si1 C33 106.11(11) . . ? C27 Si1 C33 108.45(13) . . ? C21 Si1 C33 109.90(13) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.534 _refine_diff_density_min -0.932 _refine_diff_density_rms 0.084