Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Rees, Charles' 'Guillard, Jerome' 'Meth-Cohn, Otto' 'White, Andrew J. P.' 'WIlliams, David J.' _publ_contact_author_name 'Prof Charles Rees' _publ_contact_author_address ; Prof Charles Rees Chemistry Imperial College South Kensington London SW7 2AY UNITED KINGDOM ; _publ_contact_author_email 'C.REES@IC.AC.UK' _publ_section_title ; Direct conversion of macrocyclic furans into macrocyclic isothiazoles ; data_5 #(OMC0004) _database_code_CSD 174287 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C42 H47 N O6 S' _chemical_formula_weight 693.87 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.3331 0.5567 '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 12.234(2) _cell_length_b 13.685(2) _cell_length_c 14.102(3) _cell_angle_alpha 85.07(2) _cell_angle_beta 69.152(15) _cell_angle_gamma 64.010(13) _cell_volume 1976.4(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 20 _cell_measurement_theta_min 11.10 _cell_measurement_theta_max 19.92 _exptl_crystal_description prisms _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.166 _exptl_crystal_density_method ? _exptl_crystal_F_000 740 _exptl_absorpt_coefficient_mu 1.090 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6187 _diffrn_reflns_av_R_equivalents 0.0299 _diffrn_reflns_av_sigmaI/netI 0.0616 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.37 _diffrn_reflns_theta_max 60.00 _reflns_number_total 5868 _reflns_number_observed 3835 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 614 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0742P)^2^+0.1346P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0034(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 5254 _refine_ls_number_parameters 452 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0983 _refine_ls_R_factor_obs 0.0596 _refine_ls_wR_factor_all 0.1711 _refine_ls_wR_factor_obs 0.1449 _refine_ls_goodness_of_fit_all 1.059 _refine_ls_goodness_of_fit_obs 1.146 _refine_ls_restrained_S_all 1.076 _refine_ls_restrained_S_obs 1.146 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group S1 S 0.10210(13) 0.26478(11) 1.15530(8) 0.0780(4) Uani 1 d . . N2 N 0.0889(4) 0.1825(3) 1.0859(3) 0.0761(10) Uani 1 d . . C3 C 0.1452(4) 0.1894(3) 0.9877(3) 0.0540(9) Uani 1 d . . C4 C 0.2012(3) 0.2641(3) 0.9663(3) 0.0531(8) Uani 1 d . . H4A H 0.2434(3) 0.2778(3) 0.9011(3) 0.064 Uiso 1 calc R . C5 C 0.1851(3) 0.3136(3) 1.0542(3) 0.0512(8) Uani 1 d . . C6 C 0.2221(3) 0.3969(3) 1.0757(3) 0.0530(9) Uani 1 d . . O6 O 0.2139(3) 0.4117(3) 1.1626(2) 0.0778(8) Uani 1 d . . C7 C 0.2614(3) 0.4690(3) 0.9930(3) 0.0521(8) Uani 1 d . . C8 C 0.1344(4) 0.5565(3) 0.9829(3) 0.0699(11) Uani 1 d . . H8A H 0.0788(4) 0.5989(3) 1.0469(3) 0.105 Uiso 1 calc R . H8B H 0.0911(4) 0.5218(3) 0.9638(3) 0.105 Uiso 1 calc R . H8C H 0.1540(4) 0.6032(3) 0.9316(3) 0.105 Uiso 1 calc R . C9 C 0.3275(5) 0.5239(4) 1.0291(4) 0.0771(12) Uani 1 d . . H9A H 0.2693(5) 0.5657(4) 1.0931(4) 0.116 Uiso 1 calc R . H9B H 0.3491(5) 0.5714(4) 0.9795(4) 0.116 Uiso 1 calc R . H9C H 0.4054(5) 0.4690(4) 1.0373(4) 0.116 Uiso 1 calc R . C10 C 0.3480(3) 0.4028(3) 0.8934(3) 0.0511(8) Uani 1 d . . O11 O 0.4537(2) 0.3090(2) 0.8966(2) 0.0555(6) Uani 1 d . . C12 C 0.5162(3) 0.2550(3) 0.8003(3) 0.0564(9) Uani 1 d . . C13 C 0.4536(4) 0.3142(3) 0.7378(3) 0.0587(9) Uani 1 d . . H13A H 0.4763(4) 0.2968(3) 0.6690(3) 0.070 Uiso 1 calc R . C14 C 0.3453(3) 0.4091(3) 0.7989(3) 0.0543(9) Uani 1 d . . H14A H 0.2841(3) 0.4650(3) 0.7768(3) 0.065 Uiso 1 calc R . C15 C 0.6327(4) 0.1481(4) 0.7878(3) 0.0675(11) Uani 1 d . . C16 C 0.5917(5) 0.0717(4) 0.8645(4) 0.102(2) Uani 1 d . . H16A H 0.6660(5) 0.0029(4) 0.8569(4) 0.153 Uiso 1 calc R . H16B H 0.5260(5) 0.0604(4) 0.8515(4) 0.153 Uiso 1 calc R . H16C H 0.5577(5) 0.1044(4) 0.9326(4) 0.153 Uiso 1 calc R . C17 C 0.7398(4) 0.1647(5) 0.8065(4) 0.100(2) Uani 1 d . . H17A H 0.8137(4) 0.0954(5) 0.7982(4) 0.149 Uiso 1 calc R . H17B H 0.7077(4) 0.1971(5) 0.8744(4) 0.149 Uiso 1 calc R . H17C H 0.7652(4) 0.2118(5) 0.7585(4) 0.149 Uiso 1 calc R . C18 C 0.6808(4) 0.0973(3) 0.6819(3) 0.0636(10) Uani 1 d . . O19 O 0.7346(2) 0.1489(2) 0.6033(2) 0.0601(7) Uani 1 d . . C20 C 0.7671(3) 0.0930(3) 0.5135(3) 0.0571(9) Uani 1 d . . C21 C 0.7361(4) 0.0094(4) 0.5333(4) 0.0721(11) Uani 1 d . . H21A H 0.7477(4) -0.0407(4) 0.4858(4) 0.087 Uiso 1 calc R . C22 C 0.6813(4) 0.0120(4) 0.6419(4) 0.0759(12) Uani 1 d . . H22A H 0.6516(4) -0.0369(4) 0.6780(4) 0.091 Uiso 1 calc R . C23 C 0.8279(4) 0.1370(4) 0.4174(3) 0.0640(10) Uani 1 d . . C24 C 0.8808(5) 0.0552(4) 0.3258(4) 0.089(2) Uani 1 d . . H24A H 0.9449(5) -0.0133(4) 0.3354(4) 0.133 Uiso 1 calc R . H24B H 0.9197(5) 0.0829(4) 0.2648(4) 0.133 Uiso 1 calc R . H24C H 0.8107(5) 0.0447(4) 0.3199(4) 0.133 Uiso 1 calc R . C25 C 0.9394(4) 0.1538(5) 0.4269(4) 0.094(2) Uani 1 d . . H25A H 1.0043(4) 0.0852(5) 0.4354(4) 0.142 Uiso 1 calc R . H25B H 0.9065(4) 0.2040(5) 0.4848(4) 0.142 Uiso 1 calc R . H25C H 0.9774(4) 0.1827(5) 0.3664(4) 0.142 Uiso 1 calc R . C26 C 0.7267(3) 0.2454(3) 0.4041(3) 0.0575(9) Uani 1 d . . O27 O 0.6365(2) 0.2414(2) 0.3681(2) 0.0584(6) Uani 1 d . . C28 C 0.5541(3) 0.3481(3) 0.3608(3) 0.0576(9) Uani 1 d . . C29 C 0.5900(5) 0.4160(4) 0.3911(3) 0.0713(11) Uani 1 d . . H29A H 0.5504(5) 0.4918(4) 0.3935(3) 0.086 Uiso 1 calc R . C30 C 0.7012(5) 0.3499(4) 0.4193(3) 0.0739(12) Uani 1 d . . H30A H 0.7468(5) 0.3748(4) 0.4434(3) 0.089 Uiso 1 calc R . C31 C 0.4573(4) 0.3636(3) 0.3117(3) 0.0576(9) Uani 1 d . . C32 C 0.5304(4) 0.3018(4) 0.2051(3) 0.0810(13) Uani 1 d . . H32A H 0.5944(4) 0.3263(4) 0.1658(3) 0.122 Uiso 1 calc R . H32B H 0.4697(4) 0.3156(4) 0.1716(3) 0.122 Uiso 1 calc R . H32C H 0.5727(4) 0.2250(4) 0.2115(3) 0.122 Uiso 1 calc R . C33 C 0.3858(4) 0.4864(4) 0.2995(4) 0.0793(13) Uani 1 d . . H33A H 0.4483(4) 0.5128(4) 0.2610(4) 0.119 Uiso 1 calc R . H33B H 0.3372(4) 0.5258(4) 0.3655(4) 0.119 Uiso 1 calc R . H33C H 0.3276(4) 0.4970(4) 0.2644(4) 0.119 Uiso 1 calc R . C34 C 0.3579(4) 0.3243(3) 0.3720(3) 0.0563(9) Uani 1 d . . O35 O 0.2976(2) 0.3564(2) 0.4749(2) 0.0550(6) Uani 1 d . . C36 C 0.1970(3) 0.3256(3) 0.5113(3) 0.0566(9) Uani 1 d . . C37 C 0.1948(5) 0.2763(4) 0.4335(3) 0.0720(12) Uani 1 d . . H37A H 0.1368(5) 0.2481(4) 0.4374(3) 0.086 Uiso 1 calc R . C38 C 0.2980(4) 0.2755(4) 0.3443(3) 0.0691(11) Uani 1 d . . H38A H 0.3197(4) 0.2467(4) 0.2792(3) 0.083 Uiso 1 calc R . C39 C 0.1207(4) 0.3454(3) 0.6237(3) 0.0590(9) Uani 1 d . . C40 C -0.0145(4) 0.3524(5) 0.6424(4) 0.091(2) Uani 1 d . . H40A H -0.0639(4) 0.3651(5) 0.7141(4) 0.137 Uiso 1 calc R . H40B H -0.0048(4) 0.2852(5) 0.6169(4) 0.137 Uiso 1 calc R . H40C H -0.0590(4) 0.4114(5) 0.6079(4) 0.137 Uiso 1 calc R . C41 C 0.1066(5) 0.4519(4) 0.6669(3) 0.0779(12) Uani 1 d . . H41A H 0.0577(5) 0.4631(4) 0.7387(3) 0.117 Uiso 1 calc R . H41B H 0.0620(5) 0.5122(4) 0.6335(3) 0.117 Uiso 1 calc R . H41C H 0.1913(5) 0.4465(4) 0.6554(3) 0.117 Uiso 1 calc R . C42 C 0.1936(3) 0.2481(3) 0.6732(3) 0.0552(9) Uani 1 d . . O43 O 0.1257(2) 0.2406(2) 0.7741(2) 0.0565(6) Uani 1 d . . C44 C 0.2047(4) 0.1440(3) 0.8036(3) 0.0559(9) Uani 1 d . . C45 C 0.3183(4) 0.0939(4) 0.7253(3) 0.0663(10) Uani 1 d . . H45A H 0.3880(4) 0.0281(4) 0.7254(3) 0.080 Uiso 1 calc R . C46 C 0.3113(4) 0.1618(4) 0.6414(3) 0.0662(10) Uani 1 d . . H46A H 0.3759(4) 0.1484(4) 0.5775(3) 0.079 Uiso 1 calc R . C47 C 0.1479(4) 0.1167(3) 0.9097(3) 0.0570(9) Uani 1 d . . C48 C 0.0094(4) 0.1304(4) 0.9306(3) 0.0713(11) Uani 1 d . . H48A H -0.0256(4) 0.1127(4) 0.9986(3) 0.107 Uiso 1 calc R . H48B H 0.0121(4) 0.0826(4) 0.8829(3) 0.107 Uiso 1 calc R . H48C H -0.0448(4) 0.2046(4) 0.9232(3) 0.107 Uiso 1 calc R . C49 C 0.2339(5) -0.0029(3) 0.9207(4) 0.0786(13) Uani 1 d . . H49A H 0.1984(5) -0.0212(3) 0.9884(4) 0.118 Uiso 1 calc R . H49B H 0.3204(5) -0.0121(3) 0.9084(4) 0.118 Uiso 1 calc R . H49C H 0.2367(5) -0.0498(3) 0.8723(4) 0.118 Uiso 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 0.1059(9) 0.0959(8) 0.0467(5) 0.0180(5) -0.0192(5) -0.0649(7) N2 0.106(3) 0.088(3) 0.053(2) 0.017(2) -0.020(2) -0.067(2) C3 0.055(2) 0.060(2) 0.049(2) 0.015(2) -0.017(2) -0.030(2) C4 0.052(2) 0.062(2) 0.047(2) 0.014(2) -0.015(2) -0.029(2) C5 0.044(2) 0.058(2) 0.049(2) 0.012(2) -0.0156(15) -0.022(2) C6 0.040(2) 0.063(2) 0.050(2) 0.007(2) -0.0151(15) -0.019(2) O6 0.089(2) 0.107(2) 0.054(2) 0.0108(15) -0.0268(15) -0.057(2) C7 0.041(2) 0.060(2) 0.057(2) 0.008(2) -0.017(2) -0.024(2) C8 0.052(2) 0.059(2) 0.079(3) 0.010(2) -0.019(2) -0.012(2) C9 0.082(3) 0.096(3) 0.077(3) 0.009(2) -0.029(2) -0.059(3) C10 0.038(2) 0.062(2) 0.054(2) 0.014(2) -0.0178(15) -0.023(2) O11 0.0394(12) 0.066(2) 0.0516(14) 0.0107(11) -0.0154(10) -0.0173(11) C12 0.044(2) 0.069(2) 0.050(2) 0.007(2) -0.012(2) -0.022(2) C13 0.054(2) 0.071(2) 0.049(2) 0.011(2) -0.017(2) -0.027(2) C14 0.047(2) 0.060(2) 0.058(2) 0.017(2) -0.023(2) -0.023(2) C15 0.050(2) 0.074(3) 0.057(2) 0.012(2) -0.017(2) -0.012(2) C16 0.092(3) 0.083(3) 0.072(3) 0.030(3) -0.013(3) -0.005(3) C17 0.052(2) 0.146(5) 0.078(3) -0.015(3) -0.029(2) -0.014(3) C18 0.045(2) 0.065(3) 0.064(2) 0.014(2) -0.014(2) -0.016(2) O19 0.0526(14) 0.069(2) 0.0542(14) 0.0066(12) -0.0137(11) -0.0265(13) C20 0.043(2) 0.064(2) 0.054(2) 0.002(2) -0.017(2) -0.014(2) C21 0.061(2) 0.068(3) 0.080(3) -0.005(2) -0.023(2) -0.021(2) C22 0.063(3) 0.064(3) 0.085(3) 0.011(2) -0.014(2) -0.025(2) C23 0.043(2) 0.084(3) 0.053(2) 0.005(2) -0.015(2) -0.019(2) C24 0.069(3) 0.093(3) 0.067(3) -0.010(2) -0.017(2) -0.006(3) C25 0.056(3) 0.151(5) 0.083(3) 0.035(3) -0.027(2) -0.054(3) C26 0.048(2) 0.074(3) 0.053(2) 0.008(2) -0.019(2) -0.029(2) O27 0.0485(13) 0.060(2) 0.065(2) 0.0090(12) -0.0214(12) -0.0219(12) C28 0.049(2) 0.054(2) 0.059(2) 0.013(2) -0.015(2) -0.019(2) C29 0.080(3) 0.064(3) 0.069(3) 0.012(2) -0.024(2) -0.034(2) C30 0.079(3) 0.083(3) 0.074(3) 0.014(2) -0.030(2) -0.047(3) C31 0.049(2) 0.063(2) 0.054(2) 0.016(2) -0.016(2) -0.022(2) C32 0.066(3) 0.107(4) 0.055(2) 0.005(2) -0.017(2) -0.027(3) C33 0.064(2) 0.072(3) 0.096(3) 0.035(2) -0.029(2) -0.028(2) C34 0.058(2) 0.063(2) 0.050(2) 0.015(2) -0.023(2) -0.028(2) O35 0.0508(13) 0.067(2) 0.0497(13) 0.0076(11) -0.0157(11) -0.0306(12) C36 0.049(2) 0.071(2) 0.056(2) 0.016(2) -0.021(2) -0.032(2) C37 0.088(3) 0.094(3) 0.067(3) 0.027(2) -0.042(2) -0.061(3) C38 0.085(3) 0.086(3) 0.052(2) 0.014(2) -0.028(2) -0.049(3) C39 0.049(2) 0.070(2) 0.060(2) 0.017(2) -0.020(2) -0.029(2) C40 0.053(2) 0.142(5) 0.084(3) 0.036(3) -0.027(2) -0.050(3) C41 0.080(3) 0.069(3) 0.069(3) 0.006(2) -0.018(2) -0.026(2) C42 0.050(2) 0.071(2) 0.051(2) 0.012(2) -0.016(2) -0.034(2) O43 0.0520(13) 0.0604(15) 0.0527(14) 0.0127(11) -0.0139(11) -0.0258(12) C44 0.054(2) 0.058(2) 0.055(2) 0.009(2) -0.018(2) -0.026(2) C45 0.054(2) 0.070(3) 0.067(2) 0.007(2) -0.020(2) -0.021(2) C46 0.055(2) 0.081(3) 0.056(2) 0.008(2) -0.014(2) -0.028(2) C47 0.066(2) 0.053(2) 0.057(2) 0.013(2) -0.022(2) -0.033(2) C48 0.072(3) 0.084(3) 0.071(3) 0.012(2) -0.023(2) -0.048(2) C49 0.095(3) 0.058(3) 0.079(3) 0.020(2) -0.029(3) -0.034(2) _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 N2 1.647(4) . ? S1 C5 1.707(3) . ? N2 C3 1.325(5) . ? C3 C4 1.421(5) . ? C3 C47 1.529(5) . ? C4 C5 1.374(5) . ? C5 C6 1.485(5) . ? C6 O6 1.221(4) . ? C6 C7 1.544(5) . ? C7 C10 1.495(5) . ? C7 C8 1.538(5) . ? C7 C9 1.540(5) . ? C10 C14 1.340(5) . ? C10 O11 1.377(4) . ? O11 C12 1.382(4) . ? C12 C13 1.355(5) . ? C12 C15 1.497(5) . ? C13 C14 1.433(5) . ? C15 C18 1.501(6) . ? C15 C17 1.534(7) . ? C15 C16 1.547(6) . ? C18 C22 1.336(6) . ? C18 O19 1.384(5) . ? O19 C20 1.374(5) . ? C20 C21 1.335(6) . ? C20 C23 1.512(5) . ? C21 C22 1.433(6) . ? C23 C26 1.509(6) . ? C23 C25 1.531(6) . ? C23 C24 1.537(6) . ? C26 C30 1.342(6) . ? C26 O27 1.390(4) . ? O27 C28 1.385(4) . ? C28 C29 1.341(6) . ? C28 C31 1.504(5) . ? C29 C30 1.440(6) . ? C31 C34 1.500(5) . ? C31 C32 1.540(6) . ? C31 C33 1.546(6) . ? C34 C38 1.347(6) . ? C34 O35 1.381(4) . ? O35 C36 1.387(4) . ? C36 C37 1.350(6) . ? C36 C39 1.502(5) . ? C37 C38 1.427(6) . ? C39 C42 1.516(5) . ? C39 C40 1.539(5) . ? C39 C41 1.543(6) . ? C42 C46 1.346(6) . ? C42 O43 1.390(4) . ? O43 C44 1.389(4) . ? C44 C45 1.351(5) . ? C44 C47 1.501(5) . ? C45 C46 1.444(6) . ? C47 C48 1.539(6) . ? C47 C49 1.540(6) . ? 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 N2 S1 C5 95.3(2) . . ? C3 N2 S1 110.3(3) . . ? N2 C3 C4 114.7(3) . . ? N2 C3 C47 118.8(3) . . ? C4 C3 C47 126.4(3) . . ? C5 C4 C3 111.4(3) . . ? C4 C5 C6 133.8(3) . . ? C4 C5 S1 108.2(3) . . ? C6 C5 S1 117.9(3) . . ? O6 C6 C5 118.3(3) . . ? O6 C6 C7 120.1(4) . . ? C5 C6 C7 121.5(3) . . ? C10 C7 C8 109.5(3) . . ? C10 C7 C9 111.8(3) . . ? C8 C7 C9 109.7(3) . . ? C10 C7 C6 110.6(3) . . ? C8 C7 C6 106.4(3) . . ? C9 C7 C6 108.7(3) . . ? C14 C10 O11 109.4(3) . . ? C14 C10 C7 135.1(3) . . ? O11 C10 C7 115.4(3) . . ? C10 O11 C12 107.2(3) . . ? C13 C12 O11 109.5(3) . . ? C13 C12 C15 134.7(4) . . ? O11 C12 C15 115.9(3) . . ? C12 C13 C14 106.2(3) . . ? C10 C14 C13 107.8(3) . . ? C12 C15 C18 108.4(3) . . ? C12 C15 C17 110.6(4) . . ? C18 C15 C17 110.5(3) . . ? C12 C15 C16 109.0(3) . . ? C18 C15 C16 108.5(4) . . ? C17 C15 C16 109.8(4) . . ? C22 C18 O19 108.5(4) . . ? C22 C18 C15 135.0(4) . . ? O19 C18 C15 116.5(4) . . ? C20 O19 C18 107.5(3) . . ? C21 C20 O19 109.6(3) . . ? C21 C20 C23 134.6(4) . . ? O19 C20 C23 115.8(4) . . ? C20 C21 C22 106.6(4) . . ? C18 C22 C21 107.8(4) . . ? C26 C23 C20 109.2(3) . . ? C26 C23 C25 108.9(4) . . ? C20 C23 C25 109.3(3) . . ? C26 C23 C24 110.5(3) . . ? C20 C23 C24 109.5(4) . . ? C25 C23 C24 109.5(4) . . ? C30 C26 O27 109.4(3) . . ? C30 C26 C23 134.5(4) . . ? O27 C26 C23 116.2(3) . . ? C28 O27 C26 107.0(3) . . ? C29 C28 O27 109.4(4) . . ? C29 C28 C31 133.8(4) . . ? O27 C28 C31 116.4(3) . . ? C28 C29 C30 107.3(4) . . ? C26 C30 C29 107.0(4) . . ? C34 C31 C28 113.3(3) . . ? C34 C31 C32 108.8(4) . . ? C28 C31 C32 109.2(3) . . ? C34 C31 C33 108.5(3) . . ? C28 C31 C33 108.6(4) . . ? C32 C31 C33 108.4(4) . . ? C38 C34 O35 109.5(3) . . ? C38 C34 C31 132.4(4) . . ? O35 C34 C31 117.2(3) . . ? C34 O35 C36 107.1(3) . . ? C37 C36 O35 109.0(3) . . ? C37 C36 C39 133.3(4) . . ? O35 C36 C39 117.5(3) . . ? C36 C37 C38 107.4(4) . . ? C34 C38 C37 107.1(4) . . ? C36 C39 C42 107.1(3) . . ? C36 C39 C40 108.9(3) . . ? C42 C39 C40 109.2(3) . . ? C36 C39 C41 110.7(3) . . ? C42 C39 C41 110.8(3) . . ? C40 C39 C41 110.0(4) . . ? C46 C42 O43 109.6(3) . . ? C46 C42 C39 134.8(3) . . ? O43 C42 C39 115.6(3) . . ? C44 O43 C42 107.0(3) . . ? C45 C44 O43 109.4(3) . . ? C45 C44 C47 134.5(4) . . ? O43 C44 C47 116.1(3) . . ? C44 C45 C46 107.0(4) . . ? C42 C46 C45 107.0(3) . . ? C44 C47 C3 110.5(3) . . ? C44 C47 C48 110.5(3) . . ? C3 C47 C48 109.9(3) . . ? C44 C47 C49 108.8(3) . . ? C3 C47 C49 108.3(3) . . ? C48 C47 C49 108.9(3) . . ? _refine_diff_density_max 0.393 _refine_diff_density_min -0.187 _refine_diff_density_rms 0.041 data_2 #(OMC0003) _database_code_CSD 174288 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C28 H30 N2 O4 S2' _chemical_formula_weight 522.66 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 21.0015(15) _cell_length_b 6.8083(5) _cell_length_c 19.5208(13) _cell_angle_alpha 90.00 _cell_angle_beta 101.895(6) _cell_angle_gamma 90.00 _cell_volume 2731.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 24 _cell_measurement_theta_min 11.21 _cell_measurement_theta_max 24.80 _exptl_crystal_description needles _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.271 _exptl_crystal_density_method ? _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 2.056 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7934 _exptl_absorpt_correction_T_max 0.9499 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2210 _diffrn_reflns_av_R_equivalents 0.0216 _diffrn_reflns_av_sigmaI/netI 0.0359 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 4.30 _diffrn_reflns_theta_max 61.98 _reflns_number_total 2148 _reflns_number_observed 1687 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 172 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0466P)^2^+4.3086P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00028(7) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1976 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0692 _refine_ls_R_factor_obs 0.0493 _refine_ls_wR_factor_all 0.1285 _refine_ls_wR_factor_obs 0.1109 _refine_ls_goodness_of_fit_all 1.051 _refine_ls_goodness_of_fit_obs 1.074 _refine_ls_restrained_S_all 1.094 _refine_ls_restrained_S_obs 1.074 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group S1 S 0.49770(4) -0.19784(12) 0.92198(5) 0.0543(3) Uani 1 d . . N2 N 0.57110(13) -0.1051(4) 0.9259(2) 0.0530(7) Uani 1 d . . C3 C 0.56641(15) 0.0702(4) 0.89723(14) 0.0384(7) Uani 1 d . . C4 C 0.50192(14) 0.1364(4) 0.87061(14) 0.0374(6) Uani 1 d . . H4A H 0.49165(14) 0.2573(4) 0.84903(14) 0.045 Uiso 1 calc R . C5 C 0.45723(15) 0.0016(4) 0.88052(14) 0.0384(6) Uani 1 d . . C6 C 0.38538(15) -0.0011(4) 0.86538(14) 0.0389(7) Uani 1 d . . O6 O 0.35838(12) -0.1544(3) 0.87456(14) 0.0577(6) Uani 1 d . . C7 C 0.34671(13) 0.1860(4) 0.84303(14) 0.0362(6) Uani 1 d . . C8 C 0.3591(2) 0.3276(5) 0.9061(2) 0.0475(7) Uani 1 d . . H8A H 0.3463(2) 0.2657(5) 0.9453(2) 0.071 Uiso 1 calc R . H8B H 0.3342(2) 0.4454(5) 0.8941(2) 0.071 Uiso 1 calc R . H8C H 0.4045(2) 0.3599(5) 0.9181(2) 0.071 Uiso 1 calc R . C9 C 0.2742(2) 0.1343(6) 0.8241(2) 0.0537(8) Uani 1 d . . H9A H 0.2615(2) 0.0723(6) 0.8634(2) 0.081 Uiso 1 calc R . H9B H 0.2664(2) 0.0463(6) 0.7848(2) 0.081 Uiso 1 calc R . H9C H 0.2492(2) 0.2521(6) 0.8122(2) 0.081 Uiso 1 calc R . C10 C 0.36663(12) 0.2826(4) 0.78192(13) 0.0315(6) Uani 1 d . . O11 O 0.36220(9) 0.1677(3) 0.72331(9) 0.0337(4) Uani 1 d . . C12 C 0.37625(12) 0.2870(4) 0.67128(13) 0.0336(6) Uani 1 d . . C13 C 0.38989(14) 0.4685(4) 0.6969(2) 0.0409(7) Uani 1 d . . H13A H 0.40104(14) 0.5761(4) 0.6725(2) 0.049 Uiso 1 calc R . C14 C 0.38416(15) 0.4663(4) 0.7686(2) 0.0403(7) Uani 1 d . . H14A H 0.39117(15) 0.5711(4) 0.7998(2) 0.048 Uiso 1 calc R . C15 C 0.37218(14) 0.1946(5) 0.60102(14) 0.0387(6) Uani 1 d . . C16 C 0.3101(2) 0.0713(6) 0.5816(2) 0.0590(9) Uani 1 d . . H16A H 0.3080(2) 0.0126(6) 0.5364(2) 0.089 Uiso 1 calc R . H16B H 0.2729(2) 0.1539(6) 0.5802(2) 0.089 Uiso 1 calc R . H16C H 0.3107(2) -0.0300(6) 0.6159(2) 0.089 Uiso 1 calc R . C17 C 0.3718(2) 0.3566(5) 0.5465(2) 0.0526(8) Uani 1 d . . H17A H 0.3691(2) 0.2984(5) 0.5012(2) 0.079 Uiso 1 calc R . H17B H 0.4110(2) 0.4324(5) 0.5587(2) 0.079 Uiso 1 calc R . H17C H 0.3348(2) 0.4406(5) 0.5454(2) 0.079 Uiso 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 0.0508(5) 0.0394(4) 0.0717(6) 0.0200(4) 0.0104(4) 0.0050(4) N2 0.048(2) 0.045(2) 0.064(2) 0.0150(13) 0.0077(13) 0.0095(12) C3 0.046(2) 0.043(2) 0.0275(12) 0.0035(12) 0.0092(11) 0.0091(13) C4 0.043(2) 0.0335(15) 0.0367(14) 0.0080(12) 0.0102(12) 0.0062(12) C5 0.046(2) 0.036(2) 0.0346(13) 0.0005(12) 0.0119(12) 0.0021(13) C6 0.049(2) 0.035(2) 0.0352(14) -0.0041(12) 0.0145(12) -0.0027(13) O6 0.0573(14) 0.0416(13) 0.076(2) 0.0046(11) 0.0175(12) -0.0100(11) C7 0.0384(14) 0.0383(15) 0.0326(13) -0.0028(12) 0.0093(11) -0.0004(12) C8 0.062(2) 0.045(2) 0.038(2) -0.0072(14) 0.0170(14) 0.008(2) C9 0.040(2) 0.067(2) 0.056(2) 0.003(2) 0.0140(14) -0.004(2) C10 0.0291(12) 0.0351(14) 0.0293(12) -0.0026(11) 0.0035(10) 0.0047(11) O11 0.0392(10) 0.0314(10) 0.0312(9) -0.0011(8) 0.0091(7) -0.0028(8) C12 0.0314(13) 0.0373(15) 0.0331(13) 0.0056(12) 0.0092(10) -0.0013(11) C13 0.044(2) 0.035(2) 0.044(2) 0.0041(13) 0.0117(13) -0.0010(13) C14 0.046(2) 0.0325(15) 0.042(2) -0.0043(12) 0.0075(12) 0.0000(13) C15 0.0372(14) 0.048(2) 0.0320(13) 0.0007(12) 0.0090(11) -0.0044(13) C16 0.042(2) 0.083(3) 0.050(2) -0.018(2) 0.0058(14) -0.017(2) C17 0.059(2) 0.061(2) 0.038(2) 0.0103(15) 0.0099(14) 0.005(2) _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 N2 1.653(3) . ? S1 C5 1.714(3) . ? N2 C3 1.313(4) . ? C3 C4 1.420(4) . ? C3 C15 1.538(4) 2_656 ? C4 C5 1.354(4) . ? C5 C6 1.477(4) . ? C6 O6 1.219(4) . ? C6 C7 1.525(4) . ? C7 C10 1.496(4) . ? C7 C9 1.533(4) . ? C7 C8 1.543(4) . ? C10 C14 1.344(4) . ? C10 O11 1.373(3) . ? O11 C12 1.379(3) . ? C12 C13 1.342(4) . ? C12 C15 1.495(4) . ? C13 C14 1.429(4) . ? C15 C16 1.531(4) . ? C15 C17 1.531(4) . ? C15 C3 1.538(4) 2_656 ? 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 N2 S1 C5 94.94(14) . . ? C3 N2 S1 109.9(2) . . ? N2 C3 C4 115.2(3) . . ? N2 C3 C15 120.2(3) . 2_656 ? C4 C3 C15 124.4(3) . 2_656 ? C5 C4 C3 111.7(3) . . ? C4 C5 C6 133.6(3) . . ? C4 C5 S1 108.2(2) . . ? C6 C5 S1 118.1(2) . . ? O6 C6 C5 117.9(3) . . ? O6 C6 C7 121.4(3) . . ? C5 C6 C7 120.6(2) . . ? C10 C7 C6 112.1(2) . . ? C10 C7 C9 109.6(2) . . ? C6 C7 C9 108.8(3) . . ? C10 C7 C8 109.4(2) . . ? C6 C7 C8 107.5(2) . . ? C9 C7 C8 109.4(2) . . ? C14 C10 O11 110.1(2) . . ? C14 C10 C7 134.2(3) . . ? O11 C10 C7 115.6(2) . . ? C10 O11 C12 106.9(2) . . ? C13 C12 O11 109.2(2) . . ? C13 C12 C15 134.2(3) . . ? O11 C12 C15 116.6(2) . . ? C12 C13 C14 107.5(3) . . ? C10 C14 C13 106.3(3) . . ? C12 C15 C16 110.1(2) . . ? C12 C15 C17 109.0(3) . . ? C16 C15 C17 109.9(3) . . ? C12 C15 C3 108.8(2) . 2_656 ? C16 C15 C3 111.7(3) . 2_656 ? C17 C15 C3 107.3(2) . 2_656 ? _refine_diff_density_max 0.329 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.047 data_4 #(OMC0007) _database_code_CSD 174289 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C28 H28 N4 O4 S4' _chemical_formula_weight 612.78 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.119(2) _cell_length_b 10.052(2) _cell_length_c 10.710(3) _cell_angle_alpha 83.539(15) _cell_angle_beta 74.42(2) _cell_angle_gamma 82.83(2) _cell_volume 730.0(3) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 13 _cell_measurement_theta_min 4.45 _cell_measurement_theta_max 24.07 _exptl_crystal_description needles _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.043 _exptl_crystal_size_mid 0.027 _exptl_crystal_size_min 0.027 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.394 _exptl_crystal_density_method ? _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 3.332 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2358 _diffrn_reflns_av_R_equivalents 0.0726 _diffrn_reflns_av_sigmaI/netI 0.1216 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 4.30 _diffrn_reflns_theta_max 59.98 _reflns_number_total 2154 _reflns_number_observed 1187 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 349 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0326P)^2^+2.1253P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1805 _refine_ls_number_parameters 261 _refine_ls_number_restraints 261 _refine_ls_R_factor_all 0.1732 _refine_ls_R_factor_obs 0.0837 _refine_ls_wR_factor_all 0.2120 _refine_ls_wR_factor_obs 0.1514 _refine_ls_goodness_of_fit_all 1.081 _refine_ls_goodness_of_fit_obs 1.204 _refine_ls_restrained_S_all 1.133 _refine_ls_restrained_S_obs 1.072 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group S1 S 0.6397(4) 0.1593(3) 0.4461(2) 0.0536(7) Uani 0.90 d PD 1 N2 N 0.4512(12) 0.1515(7) 0.5741(7) 0.054(2) Uani 0.90 d PD 1 C3 C 0.4771(15) 0.2211(9) 0.6656(9) 0.046(2) Uani 0.90 d PD 1 C4 C 0.6534(14) 0.2800(8) 0.6328(8) 0.044(2) Uani 0.90 d PD 1 H4A H 0.6912(14) 0.3303(8) 0.6881(8) 0.053 Uiso 0.90 calc PR 1 C5 C 0.7621(14) 0.2561(8) 0.5126(9) 0.042(2) Uani 0.90 d PD 1 C6 C 0.9583(14) 0.2998(9) 0.4521(9) 0.046(2) Uani 0.90 d PD 1 O6 O 1.0327(10) 0.3625(7) 0.5145(7) 0.067(2) Uani 0.90 d PD 1 C7 C 1.0781(14) 0.2621(9) 0.3173(9) 0.042(2) Uani 0.90 d PD 1 C8 C 1.1523(18) 0.1121(10) 0.3323(11) 0.060(3) Uani 0.90 d PD 1 H8A H 1.0426(18) 0.0601(10) 0.3657(11) 0.091 Uiso 0.90 calc PR 1 H8B H 1.2344(18) 0.0992(10) 0.3915(11) 0.091 Uiso 0.90 calc PR 1 H8C H 1.2262(18) 0.0836(10) 0.2491(11) 0.091 Uiso 0.90 calc PR 1 C9 C 1.2527(13) 0.3417(10) 0.2649(10) 0.056(2) Uani 0.90 d PD 1 H9A H 1.3233(13) 0.3147(10) 0.1804(10) 0.084 Uiso 0.90 calc PR 1 H9B H 1.3370(13) 0.3252(10) 0.3226(10) 0.084 Uiso 0.90 calc PR 1 H9C H 1.2089(13) 0.4359(10) 0.2583(10) 0.084 Uiso 0.90 calc PR 1 C16 C 0.3249(15) 0.2244(9) 0.7963(9) 0.052(2) Uani 0.90 d PD 1 C17 C 0.1381(14) 0.1649(9) 0.7958(10) 0.060(3) Uani 0.90 d PD 1 H17A H 0.1690(14) 0.0722(9) 0.7774(10) 0.090 Uiso 0.90 calc PR 1 H17B H 0.0818(14) 0.2140(9) 0.7303(10) 0.090 Uiso 0.90 calc PR 1 H17C H 0.0462(14) 0.1710(9) 0.8794(10) 0.090 Uiso 0.90 calc PR 1 C18 C 0.4188(21) 0.1402(11) 0.8991(10) 0.081(4) Uani 0.90 d PD 1 H18A H 0.4449(21) 0.0479(11) 0.8791(10) 0.121 Uiso 0.90 calc PR 1 H18B H 0.3302(21) 0.1461(11) 0.9840(10) 0.121 Uiso 0.90 calc PR 1 H18C H 0.5392(21) 0.1746(11) 0.8978(10) 0.121 Uiso 0.90 calc PR 1 C10 C 0.9585(15) 0.2794(9) 0.2162(9) 0.048(3) Uani 0.90 d PD 1 O10 O 0.9550(13) 0.1856(7) 0.1517(8) 0.063(2) Uani 0.90 d PD 1 C11 C 0.8530(15) 0.4059(9) 0.1902(8) 0.046(3) Uani 0.90 d PD 1 S12 S 0.7455(19) 0.4256(6) 0.0635(10) 0.054(2) Uani 0.90 d PD 1 N13 N 0.6655(15) 0.5859(9) 0.0794(10) 0.059(3) Uani 0.90 d PD 1 C14 C 0.7182(14) 0.6290(9) 0.1749(8) 0.045(2) Uani 0.90 d PD 1 C15 C 0.8268(15) 0.5279(9) 0.2419(9) 0.043(3) Uani 0.90 d PD 1 H15A H 0.8733(15) 0.5434(9) 0.3117(9) 0.052 Uiso 0.90 calc PR 1 S1' S 0.6945(39) 0.2810(28) 0.7146(25) 0.083(7) Uiso 0.10 d PDU 2 N2' N 0.8900(45) 0.2895(36) 0.5919(33) 0.058(14) Uiso 0.10 d PDU 2 C3' C 0.8486(52) 0.2592(37) 0.4854(31) 0.041(18) Uiso 0.10 d PDU 2 C4' C 0.6574(53) 0.2274(46) 0.5034(31) 0.049(16) Uiso 0.10 d PDU 2 H4'A H 0.6096(53) 0.2033(46) 0.4373(31) 0.058 Uiso 0.10 calc PR 2 C5' C 0.5503(44) 0.2355(43) 0.6264(38) 0.061(20) Uiso 0.10 d PDU 2 C6' C 0.3438(53) 0.2087(67) 0.6757(40) 0.069(18) Uiso 0.10 d PDU 2 O6' O 0.2694(61) 0.1548(51) 0.6053(41) 0.052(13) Uiso 0.10 d PDU 2 C7' C 0.2384(64) 0.2123(50) 0.8196(38) 0.066(20) Uiso 0.10 d PDU 2 C8' C 0.3617(127) 0.1249(70) 0.8984(69) 0.099(33) Uiso 0.10 d PDU 2 H8'A H 0.4898(127) 0.1555(70) 0.8780(69) 0.148 Uiso 0.10 calc PR 2 H8'B H 0.3730(127) 0.0332(70) 0.8778(69) 0.148 Uiso 0.10 calc PR 2 H8'C H 0.3004(127) 0.1305(70) 0.9895(69) 0.148 Uiso 0.10 calc PR 2 C9' C 0.0358(76) 0.1649(66) 0.8510(63) 0.063(22) Uiso 0.10 d PDU 2 H9'A H -0.0414(76) 0.2208(66) 0.8007(63) 0.094 Uiso 0.10 calc PR 2 H9'B H -0.0261(76) 0.1706(66) 0.9420(63) 0.094 Uiso 0.10 calc PR 2 H9'C H 0.0465(76) 0.0734(66) 0.8303(63) 0.094 Uiso 0.10 calc PR 2 C16' C 1.0069(59) 0.2575(50) 0.3578(33) 0.047(19) Uiso 0.10 d PDU 2 C17' C 1.1678(80) 0.3451(83) 0.3462(60) 0.069(23) Uiso 0.10 d PDU 2 H17D H 1.2606(80) 0.3377(83) 0.2630(60) 0.103 Uiso 0.10 calc PR 2 H17E H 1.2327(80) 0.3167(83) 0.4140(60) 0.103 Uiso 0.10 calc PR 2 H17F H 1.1131(80) 0.4370(83) 0.3542(60) 0.103 Uiso 0.10 calc PR 2 C18' C 1.1054(113) 0.1051(61) 0.3575(60) 0.099(35) Uiso 0.10 d PDU 2 H18D H 1.0071(113) 0.0454(61) 0.3648(60) 0.148 Uiso 0.10 calc PR 2 H18E H 1.1629(113) 0.0849(61) 0.4298(60) 0.148 Uiso 0.10 calc PR 2 H18F H 1.2051(113) 0.0940(61) 0.2778(60) 0.148 Uiso 0.10 calc PR 2 C10' C 0.0667(106) 0.7220(50) 0.7652(43) 0.073(22) Uiso 0.10 d PDU 2 O10' O 0.1217(89) 0.8201(51) 0.8037(54) 0.044(17) Uiso 0.10 d PDU 2 C11' C 0.1369(84) 0.5902(47) 0.8083(43) 0.063(22) Uiso 0.10 d PDU 2 S12' S 0.2508(155) 0.5683(51) 0.9318(81) 0.048(18) Uiso 0.10 d PDU 2 N13' N 0.2912(139) 0.4018(54) 0.9320(76) 0.069(21) Uiso 0.10 d PDU 2 C14' C 0.2248(69) 0.3605(49) 0.8432(45) 0.059(21) Uiso 0.10 d PDU 2 C15' C 0.1326(80) 0.4656(50) 0.7691(41) 0.053(21) Uiso 0.10 d PDU 2 H15B H 0.0773(80) 0.4505(50) 0.7031(41) 0.063 Uiso 0.10 calc PR 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.058(2) 0.065(2) 0.0394(13) -0.0140(11) -0.0070(11) -0.0136(12) N2 0.053(5) 0.055(5) 0.047(4) -0.003(4) -0.002(4) -0.004(4) C3 0.061(7) 0.035(5) 0.039(5) -0.006(4) -0.016(5) 0.013(4) C4 0.058(6) 0.042(5) 0.030(5) -0.005(4) -0.011(4) -0.001(4) C5 0.047(6) 0.028(4) 0.051(5) 0.002(4) -0.017(5) 0.004(4) C6 0.053(6) 0.039(5) 0.046(5) -0.001(4) -0.017(4) 0.004(4) O6 0.073(5) 0.072(5) 0.065(4) -0.019(4) -0.023(4) -0.020(4) C7 0.045(5) 0.045(5) 0.037(5) 0.003(4) -0.016(4) 0.002(4) C8 0.065(7) 0.055(6) 0.055(6) -0.002(5) -0.011(5) 0.006(5) C9 0.038(5) 0.063(6) 0.066(7) -0.008(5) -0.009(5) -0.008(5) C16 0.054(6) 0.055(6) 0.038(5) 0.008(4) -0.007(4) 0.007(5) C17 0.056(7) 0.043(5) 0.069(7) -0.006(5) 0.002(6) -0.001(5) C18 0.103(10) 0.068(7) 0.044(6) 0.024(5) -0.003(6) 0.036(7) C10 0.050(6) 0.037(5) 0.049(5) -0.005(4) -0.001(4) 0.000(4) O10 0.078(6) 0.051(4) 0.059(5) -0.018(4) -0.016(5) 0.000(4) C11 0.043(5) 0.060(6) 0.035(5) -0.003(4) -0.010(4) -0.002(4) S12 0.065(3) 0.058(3) 0.046(2) -0.0120(14) -0.026(2) 0.0028(15) N13 0.052(6) 0.059(5) 0.065(6) -0.009(4) -0.018(5) 0.008(4) C14 0.042(5) 0.059(6) 0.031(5) -0.005(4) -0.005(4) -0.001(4) C15 0.045(6) 0.047(5) 0.041(5) -0.017(4) -0.012(4) -0.002(4) _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 N2 1.644(8) . ? S1 C5 1.707(9) . ? N2 C3 1.329(11) . ? C3 C4 1.397(13) . ? C3 C16 1.524(13) . ? C4 C5 1.342(12) . ? C5 C6 1.472(13) . ? C6 O6 1.222(10) . ? C6 C7 1.528(12) . ? C7 C9 1.507(12) . ? C7 C10 1.531(12) . ? C7 C8 1.539(12) . ? C16 C14 1.516(12) 2_666 ? C16 C17 1.526(13) . ? C16 C18 1.556(12) . ? C10 O10 1.236(10) . ? C10 C11 1.433(11) . ? C11 C15 1.373(11) . ? C11 S12 1.710(8) . ? S12 N13 1.652(8) . ? N13 C14 1.312(10) . ? C14 C15 1.443(11) . ? C14 C16 1.516(12) 2_666 ? S1' N2' 1.64(2) . ? S1' C5' 1.70(3) . ? N2' C3' 1.33(3) . ? C3' C4' 1.39(3) . ? C3' C16' 1.52(2) . ? C4' C5' 1.34(3) . ? C5' C6' 1.47(2) . ? C6' O6' 1.23(3) . ? C6' C7' 1.52(3) . ? C7' C9' 1.51(3) . ? C7' C8' 1.51(3) . ? C7' C14' 1.53(2) . ? C16' C17' 1.50(3) . ? C16' C10' 1.53(3) 2_666 ? C16' C18' 1.60(3) . ? C10' O10' 1.25(3) . ? C10' C11' 1.43(2) . ? C10' C16' 1.53(3) 2_666 ? C11' C15' 1.37(2) . ? C11' S12' 1.71(2) . ? S12' N13' 1.66(2) . ? N13' C14' 1.30(2) . ? C14' C15' 1.45(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 N2 S1 C5 94.8(4) . . ? C3 N2 S1 109.7(7) . . ? N2 C3 C4 114.7(8) . . ? N2 C3 C16 119.6(9) . . ? C4 C3 C16 125.6(8) . . ? C5 C4 C3 112.5(9) . . ? C4 C5 C6 125.5(9) . . ? C4 C5 S1 108.4(8) . . ? C6 C5 S1 126.1(7) . . ? O6 C6 C5 118.8(8) . . ? O6 C6 C7 118.6(9) . . ? C5 C6 C7 122.5(8) . . ? C9 C7 C6 112.4(7) . . ? C9 C7 C10 107.9(7) . . ? C6 C7 C10 113.4(8) . . ? C9 C7 C8 108.5(8) . . ? C6 C7 C8 106.7(7) . . ? C10 C7 C8 107.7(7) . . ? C14 C16 C3 106.1(8) 2_666 . ? C14 C16 C17 110.9(8) 2_666 . ? C3 C16 C17 112.6(8) . . ? C14 C16 C18 110.9(8) 2_666 . ? C3 C16 C18 107.4(8) . . ? C17 C16 C18 108.8(9) . . ? O10 C10 C11 118.0(8) . . ? O10 C10 C7 120.9(8) . . ? C11 C10 C7 121.1(7) . . ? C15 C11 C10 133.1(8) . . ? C15 C11 S12 107.5(6) . . ? C10 C11 S12 119.2(6) . . ? N13 S12 C11 95.8(4) . . ? C14 N13 S12 110.5(6) . . ? N13 C14 C15 114.3(7) . . ? N13 C14 C16 120.9(7) . 2_666 ? C15 C14 C16 124.7(7) . 2_666 ? C11 C15 C14 111.9(7) . . ? N2' S1' C5' 95.1(13) . . ? C3' N2' S1' 109.3(16) . . ? N2' C3' C4' 114.8(18) . . ? N2' C3' C16' 119.7(23) . . ? C4' C3' C16' 125.4(22) . . ? C5' C4' C3' 112.6(20) . . ? C4' C5' C6' 125.5(23) . . ? C4' C5' S1' 108.2(16) . . ? C6' C5' S1' 126.3(20) . . ? O6' C6' C5' 118.1(25) . . ? O6' C6' C7' 118.6(24) . . ? C5' C6' C7' 121.4(22) . . ? C9' C7' C8' 110.0(23) . . ? C9' C7' C6' 112.3(24) . . ? C8' C7' C6' 108.7(24) . . ? C9' C7' C14' 110.5(20) . . ? C8' C7' C14' 111.6(22) . . ? C6' C7' C14' 103.6(32) . . ? C17' C16' C3' 115.3(22) . . ? C17' C16' C10' 110.5(21) . 2_666 ? C3' C16' C10' 115.5(24) . 2_666 ? C17' C16' C18' 106.7(24) . . ? C3' C16' C18' 103.8(22) . . ? C10' C16' C18' 103.7(20) 2_666 . ? O10' C10' C11' 117.6(25) . . ? O10' C10' C16' 119.2(26) . 2_666 ? C11' C10' C16' 119.6(30) . 2_666 ? C15' C11' C10' 132.1(24) . . ? C15' C11' S12' 107.6(14) . . ? C10' C11' S12' 120.3(22) . . ? N13' S12' C11' 95.7(12) . . ? C14' N13' S12' 110.3(16) . . ? N13' C14' C15' 114.9(17) . . ? N13' C14' C7' 122.9(23) . . ? C15' C14' C7' 122.1(22) . . ? C11' C15' C14' 111.5(17) . . ? _refine_diff_density_max 0.331 _refine_diff_density_min -0.275 _refine_diff_density_rms 0.069