# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Jin Qu' _publ_contact_author_email qujin@nankai.edu.cn _publ_contact_author_address ; State key Laboratory of Elemento-organicemistry, Nankai University, Tianjin, China ; loop_ _publ_author_name 'Guo-Xing Li' 'Jin Qu' data_shelx _database_code_depnum_ccdc_archive 'CCDC 838866' #TrackingRef 'web_deposit_cif_file_0_Guo-XingLi_1313051034.m110620.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C48 H54 N2 O10 S2' _chemical_formula_weight 883.05 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 14.142(4) _cell_length_b 8.134(2) _cell_length_c 19.517(5) _cell_angle_alpha 90.00 _cell_angle_beta 92.482(5) _cell_angle_gamma 90.00 _cell_volume 2243.2(10) _cell_formula_units_Z 2 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 7969 _cell_measurement_theta_min 1.8 _cell_measurement_theta_max 28.0 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.307 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 0.180 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9650 _exptl_absorpt_correction_T_max 0.9788 _exptl_absorpt_process_details CrystalClear _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator multilayer _diffrn_measurement_device_type 'Rigaku Saturn724 CCD' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean 14.22 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 29214 _diffrn_reflns_av_R_equivalents 0.0409 _diffrn_reflns_av_sigmaI/netI 0.0583 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 27.89 _reflns_number_total 10708 _reflns_number_gt 9624 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'CrystalStructure 3.8' _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^)+(0.0428P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.02(5) _refine_ls_number_reflns 10708 _refine_ls_number_parameters 577 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0509 _refine_ls_R_factor_gt 0.0451 _refine_ls_wR_factor_ref 0.0937 _refine_ls_wR_factor_gt 0.0907 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.001 _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 0.14355(3) -0.11454(6) 0.63728(2) 0.02062(11) Uani 1 1 d . . . S2 S 0.32686(4) 1.06062(6) 0.85091(2) 0.02242(11) Uani 1 1 d . . . O1 O 0.16976(10) -0.13775(19) 0.70805(7) 0.0273(3) Uani 1 1 d . . . O2 O 0.09567(10) -0.24572(17) 0.59983(7) 0.0252(3) Uani 1 1 d . . . O3 O 0.00507(9) 0.23020(19) 0.52423(7) 0.0257(3) Uani 1 1 d . . . H3 H -0.0149 0.2357 0.4831 0.039 Uiso 1 1 calc R . . O4 O 0.25482(9) 0.56946(19) 0.43917(6) 0.0236(3) Uani 1 1 d . . . O5 O 0.25999(9) 0.3858(2) 0.67030(6) 0.0265(3) Uani 1 1 d . . . O6 O 0.40611(10) 1.12678(18) 0.89082(7) 0.0270(3) Uani 1 1 d . . . O7 O 0.28520(10) 1.15560(18) 0.79570(7) 0.0284(3) Uani 1 1 d . . . O8 O 0.50127(11) 0.7242(2) 0.98757(7) 0.0319(4) Uani 1 1 d . . . H8 H 0.5236 0.6939 1.0261 0.048 Uiso 1 1 calc R . . O9 O 0.24211(9) 0.3751(2) 1.04962(7) 0.0292(3) Uani 1 1 d . . . O10 O 0.25495(10) 0.60819(18) 0.82680(7) 0.0255(3) Uani 1 1 d . . . N1 N 0.06983(11) 0.0374(2) 0.63043(8) 0.0215(4) Uani 1 1 d D . . N2 N 0.36319(11) 0.8907(2) 0.81700(8) 0.0209(3) Uani 1 1 d D . . C1 C 0.24688(14) -0.0636(2) 0.59496(10) 0.0206(4) Uani 1 1 d . . . C2 C 0.32381(14) 0.0016(3) 0.63191(11) 0.0289(5) Uani 1 1 d . . . H2A H 0.3214 0.0178 0.6800 0.035 Uiso 1 1 calc R . . C3 C 0.40400(15) 0.0427(3) 0.59798(11) 0.0337(5) Uani 1 1 d . . . H3A H 0.4569 0.0874 0.6232 0.040 Uiso 1 1 calc R . . C4 C 0.40907(15) 0.0203(3) 0.52798(12) 0.0325(5) Uani 1 1 d . . . C5 C 0.33086(17) -0.0438(3) 0.49161(12) 0.0366(6) Uani 1 1 d . . . H5 H 0.3333 -0.0600 0.4435 0.044 Uiso 1 1 calc R . . C6 C 0.24919(15) -0.0845(3) 0.52477(10) 0.0280(5) Uani 1 1 d . . . H6 H 0.1955 -0.1262 0.4995 0.034 Uiso 1 1 calc R . . C7 C 0.49850(18) 0.0615(4) 0.49212(14) 0.0501(7) Uani 1 1 d . . . H7A H 0.4972 0.0078 0.4471 0.075 Uiso 1 1 calc R . . H7B H 0.5535 0.0226 0.5198 0.075 Uiso 1 1 calc R . . H7C H 0.5028 0.1808 0.4861 0.075 Uiso 1 1 calc R . . C8 C 0.09915(14) 0.2031(2) 0.65480(10) 0.0212(4) Uani 1 1 d . . . H8A H 0.1536 0.1875 0.6886 0.025 Uiso 1 1 calc R . . C9 C 0.01823(13) 0.2774(3) 0.69387(9) 0.0195(4) Uani 1 1 d . . . C10 C -0.00863(14) 0.4406(3) 0.68573(10) 0.0224(4) Uani 1 1 d . . . H10 H 0.0222 0.5078 0.6538 0.027 Uiso 1 1 calc R . . C11 C -0.08058(15) 0.5071(3) 0.72407(11) 0.0279(5) Uani 1 1 d . . . C12 C -0.12609(14) 0.4065(3) 0.76941(10) 0.0271(5) Uani 1 1 d . . . H12 H -0.1763 0.4503 0.7946 0.033 Uiso 1 1 calc R . . C13 C -0.10005(14) 0.2429(3) 0.77890(10) 0.0245(5) Uani 1 1 d . . . C14 C -0.02710(14) 0.1806(3) 0.74123(10) 0.0237(4) Uani 1 1 d . . . H14 H -0.0077 0.0697 0.7479 0.028 Uiso 1 1 calc R . . C15 C -0.1072(2) 0.6858(3) 0.71559(15) 0.0505(7) Uani 1 1 d . . . H15A H -0.1628 0.7095 0.7422 0.076 Uiso 1 1 calc R . . H15B H -0.1219 0.7091 0.6670 0.076 Uiso 1 1 calc R . . H15C H -0.0542 0.7550 0.7320 0.076 Uiso 1 1 calc R . . C16 C -0.15106(17) 0.1323(3) 0.82736(13) 0.0426(6) Uani 1 1 d . . . H16A H -0.1926 0.0571 0.8009 0.064 Uiso 1 1 calc R . . H16B H -0.1890 0.1994 0.8575 0.064 Uiso 1 1 calc R . . H16C H -0.1046 0.0687 0.8551 0.064 Uiso 1 1 calc R . . C17 C 0.13511(13) 0.3063(2) 0.59621(10) 0.0184(4) Uani 1 1 d . . . C18 C 0.08931(13) 0.3135(2) 0.53198(10) 0.0194(4) Uani 1 1 d . . . C19 C 0.12702(13) 0.3976(3) 0.47738(9) 0.0201(4) Uani 1 1 d . . . H19 H 0.0954 0.3978 0.4334 0.024 Uiso 1 1 calc R . . C20 C 0.21155(13) 0.4809(2) 0.48850(10) 0.0195(4) Uani 1 1 d . . . C21 C 0.25868(13) 0.4792(3) 0.55270(10) 0.0212(4) Uani 1 1 d . . . H21 H 0.3165 0.5372 0.5600 0.025 Uiso 1 1 calc R . . C22 C 0.22040(13) 0.3925(3) 0.60540(9) 0.0199(4) Uani 1 1 d . . . C23 C 0.19854(15) 0.6115(3) 0.37918(10) 0.0283(5) Uani 1 1 d . . . H23A H 0.1811 0.5112 0.3539 0.042 Uiso 1 1 calc R . . H23B H 0.2348 0.6839 0.3500 0.042 Uiso 1 1 calc R . . H23C H 0.1411 0.6683 0.3926 0.042 Uiso 1 1 calc R . . C24 C 0.34951(15) 0.4623(3) 0.68345(11) 0.0385(6) Uani 1 1 d . . . H24A H 0.3965 0.4119 0.6546 0.058 Uiso 1 1 calc R . . H24B H 0.3691 0.4479 0.7319 0.058 Uiso 1 1 calc R . . H24C H 0.3445 0.5799 0.6730 0.058 Uiso 1 1 calc R . . C25 C 0.23611(14) 1.0101(3) 0.90639(10) 0.0237(4) Uani 1 1 d . . . C26 C 0.14899(16) 0.9686(3) 0.87785(12) 0.0372(6) Uani 1 1 d . . . H26 H 0.1379 0.9722 0.8295 0.045 Uiso 1 1 calc R . . C27 C 0.07769(16) 0.9216(3) 0.91959(12) 0.0414(7) Uani 1 1 d . . . H27 H 0.0178 0.8910 0.8996 0.050 Uiso 1 1 calc R . . C28 C 0.09173(16) 0.9181(3) 0.99044(12) 0.0381(6) Uani 1 1 d . . . C29 C 0.18076(17) 0.9586(3) 1.01729(12) 0.0402(6) Uani 1 1 d . . . H29 H 0.1922 0.9550 1.0656 0.048 Uiso 1 1 calc R . . C30 C 0.25356(17) 1.0040(3) 0.97657(11) 0.0341(6) Uani 1 1 d . . . H30 H 0.3143 1.0306 0.9963 0.041 Uiso 1 1 calc R . . C31 C 0.01209(19) 0.8743(5) 1.03546(13) 0.0661(9) Uani 1 1 d . . . H31A H 0.0006 0.7556 1.0331 0.099 Uiso 1 1 calc R . . H31B H -0.0453 0.9332 1.0198 0.099 Uiso 1 1 calc R . . H31C H 0.0290 0.9055 1.0829 0.099 Uiso 1 1 calc R . . C32 C 0.42525(14) 0.7764(3) 0.85827(10) 0.0215(4) Uani 1 1 d . . . H32 H 0.4689 0.8482 0.8867 0.026 Uiso 1 1 calc R . . C33 C 0.48796(13) 0.6851(3) 0.80926(10) 0.0213(4) Uani 1 1 d . . . C34 C 0.51038(13) 0.5204(3) 0.81867(10) 0.0238(5) Uani 1 1 d . . . H34 H 0.4838 0.4614 0.8551 0.029 Uiso 1 1 calc R . . C35 C 0.57136(15) 0.4402(3) 0.77547(11) 0.0280(5) Uani 1 1 d . . . C36 C 0.61041(14) 0.5297(3) 0.72306(11) 0.0285(5) Uani 1 1 d . . . H36 H 0.6522 0.4760 0.6935 0.034 Uiso 1 1 calc R . . C37 C 0.59017(14) 0.6952(3) 0.71251(11) 0.0274(5) Uani 1 1 d . . . C38 C 0.52803(14) 0.7708(3) 0.75565(10) 0.0240(5) Uani 1 1 d . . . H38 H 0.5124 0.8833 0.7486 0.029 Uiso 1 1 calc R . . C39 C 0.5917(2) 0.2601(3) 0.78485(15) 0.0498(7) Uani 1 1 d . . . H39A H 0.6091 0.2382 0.8331 0.075 Uiso 1 1 calc R . . H39B H 0.6441 0.2284 0.7564 0.075 Uiso 1 1 calc R . . H39C H 0.5352 0.1963 0.7712 0.075 Uiso 1 1 calc R . . C40 C 0.63294(17) 0.7925(3) 0.65566(12) 0.0408(6) Uani 1 1 d . . . H40A H 0.6815 0.7261 0.6344 0.061 Uiso 1 1 calc R . . H40B H 0.6617 0.8932 0.6746 0.061 Uiso 1 1 calc R . . H40C H 0.5834 0.8213 0.6211 0.061 Uiso 1 1 calc R . . C41 C 0.37552(14) 0.6703(3) 0.90816(10) 0.0205(4) Uani 1 1 d . . . C42 C 0.41619(14) 0.6471(3) 0.97380(10) 0.0221(4) Uani 1 1 d . . . C43 C 0.37431(13) 0.5510(3) 1.02300(10) 0.0236(4) Uani 1 1 d . . . H43 H 0.4033 0.5388 1.0675 0.028 Uiso 1 1 calc R . . C44 C 0.28978(14) 0.4739(3) 1.00570(10) 0.0223(4) Uani 1 1 d . . . C45 C 0.24703(14) 0.4902(3) 0.94050(10) 0.0242(4) Uani 1 1 d . . . H45 H 0.1891 0.4358 0.9290 0.029 Uiso 1 1 calc R . . C46 C 0.29048(13) 0.5873(3) 0.89254(10) 0.0210(4) Uani 1 1 d . . . C47 C 0.29368(16) 0.3182(3) 1.10923(11) 0.0318(5) Uani 1 1 d . . . H47A H 0.3516 0.2630 1.0957 0.048 Uiso 1 1 calc R . . H47B H 0.2546 0.2407 1.1341 0.048 Uiso 1 1 calc R . . H47C H 0.3103 0.4118 1.1390 0.048 Uiso 1 1 calc R . . C48 C 0.16613(14) 0.5330(3) 0.80784(11) 0.0290(5) Uani 1 1 d . . . H48A H 0.1714 0.4136 0.8133 0.043 Uiso 1 1 calc R . . H48B H 0.1489 0.5591 0.7599 0.043 Uiso 1 1 calc R . . H48C H 0.1172 0.5750 0.8373 0.043 Uiso 1 1 calc R . . H1 H 0.0372(14) 0.031(3) 0.5898(7) 0.035 Uiso 1 1 d D . . H2 H 0.3177(12) 0.842(3) 0.7912(9) 0.035 Uiso 1 1 d 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 S1 0.0237(2) 0.0188(2) 0.0196(2) 0.0021(2) 0.00367(19) 0.0019(2) S2 0.0272(2) 0.0222(3) 0.0177(2) 0.0008(2) -0.0002(2) 0.0013(2) O1 0.0330(8) 0.0306(9) 0.0184(7) 0.0056(6) 0.0008(6) -0.0001(7) O2 0.0266(7) 0.0228(8) 0.0263(8) -0.0004(6) 0.0008(6) -0.0020(6) O3 0.0201(7) 0.0313(8) 0.0253(8) 0.0060(7) -0.0037(6) -0.0066(6) O4 0.0208(7) 0.0294(8) 0.0206(7) 0.0056(7) 0.0026(5) -0.0004(6) O5 0.0240(7) 0.0362(8) 0.0190(7) 0.0009(7) -0.0028(6) -0.0065(7) O6 0.0292(8) 0.0264(8) 0.0249(8) -0.0030(6) -0.0033(6) -0.0024(6) O7 0.0372(8) 0.0269(8) 0.0209(7) 0.0053(6) -0.0021(6) 0.0040(7) O8 0.0284(8) 0.0428(10) 0.0236(8) 0.0081(7) -0.0086(7) -0.0110(7) O9 0.0247(7) 0.0356(9) 0.0278(7) 0.0113(7) 0.0050(6) -0.0025(7) O10 0.0232(7) 0.0324(9) 0.0205(7) 0.0011(6) -0.0050(6) -0.0050(6) N1 0.0199(8) 0.0213(9) 0.0233(9) -0.0004(8) 0.0001(7) 0.0003(7) N2 0.0225(8) 0.0234(9) 0.0167(8) -0.0006(8) 0.0001(6) 0.0013(8) C1 0.0230(10) 0.0167(10) 0.0222(10) 0.0009(8) 0.0032(8) 0.0049(8) C2 0.0252(10) 0.0370(13) 0.0243(11) 0.0026(10) -0.0006(9) 0.0013(10) C3 0.0214(10) 0.0402(14) 0.0390(13) 0.0035(12) -0.0036(9) 0.0011(10) C4 0.0239(11) 0.0338(13) 0.0405(13) 0.0056(11) 0.0100(10) 0.0031(9) C5 0.0405(13) 0.0429(14) 0.0272(12) -0.0045(11) 0.0105(10) -0.0062(11) C6 0.0266(10) 0.0331(13) 0.0244(11) -0.0028(9) 0.0035(9) -0.0062(9) C7 0.0310(12) 0.0638(18) 0.0572(16) 0.0027(16) 0.0190(11) -0.0043(14) C8 0.0200(10) 0.0207(10) 0.0230(10) 0.0029(8) 0.0023(8) 0.0017(8) C9 0.0191(9) 0.0228(11) 0.0166(10) -0.0027(8) 0.0011(8) -0.0018(8) C10 0.0230(10) 0.0200(10) 0.0247(11) -0.0012(8) 0.0047(8) 0.0003(8) C11 0.0283(11) 0.0242(12) 0.0318(12) 0.0009(10) 0.0070(9) 0.0040(9) C12 0.0232(10) 0.0334(13) 0.0253(11) 0.0000(10) 0.0083(8) 0.0030(10) C13 0.0233(10) 0.0269(12) 0.0235(10) 0.0034(9) 0.0033(9) -0.0006(9) C14 0.0261(10) 0.0197(10) 0.0253(10) 0.0014(9) 0.0018(9) -0.0006(9) C15 0.0558(17) 0.0289(14) 0.0694(19) 0.0081(14) 0.0337(15) 0.0131(13) C16 0.0404(14) 0.0432(15) 0.0460(15) 0.0096(12) 0.0210(12) 0.0014(12) C17 0.0189(9) 0.0165(9) 0.0201(10) 0.0027(8) 0.0043(8) 0.0033(8) C18 0.0159(9) 0.0187(10) 0.0237(10) -0.0009(8) 0.0015(8) 0.0007(8) C19 0.0195(9) 0.0226(10) 0.0180(9) -0.0018(9) 0.0004(7) 0.0029(9) C20 0.0193(9) 0.0185(10) 0.0209(10) 0.0006(8) 0.0047(8) 0.0018(8) C21 0.0157(9) 0.0250(11) 0.0228(10) -0.0002(9) 0.0020(8) -0.0009(8) C22 0.0189(9) 0.0206(10) 0.0200(9) -0.0022(9) -0.0003(7) 0.0025(8) C23 0.0295(11) 0.0318(12) 0.0237(11) 0.0083(9) 0.0033(9) 0.0001(9) C24 0.0288(12) 0.0587(17) 0.0276(12) 0.0004(12) -0.0054(10) -0.0149(12) C25 0.0282(11) 0.0245(11) 0.0184(10) -0.0001(8) 0.0021(8) 0.0062(9) C26 0.0287(12) 0.0572(17) 0.0255(12) 0.0020(11) -0.0005(9) 0.0056(11) C27 0.0216(11) 0.0629(19) 0.0398(14) 0.0039(13) 0.0018(10) 0.0013(12) C28 0.0359(13) 0.0442(16) 0.0349(13) 0.0015(11) 0.0106(10) 0.0032(11) C29 0.0464(15) 0.0521(16) 0.0222(11) 0.0007(11) 0.0044(11) -0.0095(13) C30 0.0365(13) 0.0441(15) 0.0216(11) 0.0011(10) 0.0011(10) -0.0079(11) C31 0.0457(16) 0.106(3) 0.0484(16) 0.0069(19) 0.0200(13) -0.0066(19) C32 0.0217(10) 0.0256(11) 0.0168(9) 0.0027(8) -0.0017(8) -0.0005(8) C33 0.0176(9) 0.0242(11) 0.0219(10) -0.0014(9) -0.0016(8) -0.0016(8) C34 0.0214(10) 0.0255(12) 0.0247(10) 0.0043(9) 0.0037(8) 0.0000(9) C35 0.0245(10) 0.0275(12) 0.0321(12) 0.0024(10) 0.0041(9) 0.0015(9) C36 0.0240(10) 0.0334(13) 0.0286(11) -0.0021(10) 0.0071(9) 0.0009(9) C37 0.0245(11) 0.0291(12) 0.0290(11) 0.0025(10) 0.0059(9) -0.0042(9) C38 0.0260(11) 0.0200(11) 0.0259(11) 0.0017(9) 0.0022(9) -0.0025(9) C39 0.0527(16) 0.0328(15) 0.0662(19) 0.0098(13) 0.0283(14) 0.0166(13) C40 0.0414(14) 0.0404(15) 0.0421(14) 0.0065(12) 0.0194(11) 0.0008(12) C41 0.0204(10) 0.0203(10) 0.0207(10) -0.0022(8) 0.0007(8) -0.0001(8) C42 0.0202(10) 0.0232(11) 0.0230(10) -0.0006(9) 0.0004(8) -0.0014(8) C43 0.0246(10) 0.0250(11) 0.0211(10) 0.0013(9) 0.0014(8) 0.0019(9) C44 0.0218(10) 0.0228(11) 0.0231(10) 0.0018(9) 0.0088(8) 0.0039(8) C45 0.0193(9) 0.0273(11) 0.0258(11) 0.0020(9) 0.0017(8) 0.0008(9) C46 0.0188(9) 0.0234(11) 0.0210(10) 0.0001(8) 0.0029(8) 0.0023(8) C47 0.0358(12) 0.0331(12) 0.0270(11) 0.0082(10) 0.0067(10) 0.0029(10) C48 0.0250(10) 0.0324(13) 0.0289(11) -0.0010(10) -0.0050(9) -0.0048(9) _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 O1 1.4270(14) . ? S1 O2 1.4452(15) . ? S1 N1 1.6185(18) . ? S1 C1 1.759(2) . ? S2 O7 1.4318(15) . ? S2 O6 1.4413(15) . ? S2 N2 1.6255(18) . ? S2 C25 1.763(2) . ? O3 C18 1.373(2) . ? O3 H3 0.8400 . ? O4 C20 1.368(2) . ? O4 C23 1.428(2) . ? O5 C22 1.364(2) . ? O5 C24 1.424(2) . ? O8 C42 1.373(2) . ? O8 H8 0.8400 . ? O9 C44 1.373(2) . ? O9 C47 1.423(2) . ? O10 C46 1.368(2) . ? O10 C48 1.431(2) . ? N1 C8 1.483(3) . ? N1 H1 0.901(9) . ? N2 C32 1.490(2) . ? N2 H2 0.895(9) . ? C1 C6 1.382(3) . ? C1 C2 1.385(3) . ? C2 C3 1.379(3) . ? C2 H2A 0.9500 . ? C3 C4 1.383(3) . ? C3 H3A 0.9500 . ? C4 C5 1.390(3) . ? C4 C7 1.510(3) . ? C5 C6 1.388(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C17 1.523(3) . ? C8 C9 1.527(3) . ? C8 H8A 1.0000 . ? C9 C10 1.388(3) . ? C9 C14 1.391(3) . ? C10 C11 1.398(3) . ? C10 H10 0.9500 . ? C11 C12 1.384(3) . ? C11 C15 1.509(3) . ? C12 C13 1.391(3) . ? C12 H12 0.9500 . ? C13 C14 1.388(3) . ? C13 C16 1.511(3) . ? C14 H14 0.9500 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.387(3) . ? C17 C22 1.400(3) . ? C18 C19 1.392(3) . ? C19 C20 1.383(3) . ? C19 H19 0.9500 . ? C20 C21 1.394(3) . ? C21 C22 1.377(3) . ? C21 H21 0.9500 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C26 1.372(3) . ? C25 C30 1.382(3) . ? C26 C27 1.378(3) . ? C26 H26 0.9500 . ? C27 C28 1.389(3) . ? C27 H27 0.9500 . ? C28 C29 1.383(3) . ? C28 C31 1.501(3) . ? C29 C30 1.378(3) . ? C29 H29 0.9500 . ? C30 H30 0.9500 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 C41 1.499(3) . ? C32 C33 1.526(3) . ? C32 H32 1.0000 . ? C33 C34 1.386(3) . ? C33 C38 1.398(3) . ? C34 C35 1.394(3) . ? C34 H34 0.9500 . ? C35 C36 1.389(3) . ? C35 C39 1.503(3) . ? C36 C37 1.390(3) . ? C36 H36 0.9500 . ? C37 C38 1.387(3) . ? C37 C40 1.510(3) . ? C38 H38 0.9500 . ? C39 H39A 0.9800 . ? C39 H39B 0.9800 . ? C39 H39C 0.9800 . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 H40C 0.9800 . ? C41 C42 1.394(3) . ? C41 C46 1.401(3) . ? C42 C43 1.390(3) . ? C43 C44 1.379(3) . ? C43 H43 0.9500 . ? C44 C45 1.391(3) . ? C45 C46 1.388(3) . ? C45 H45 0.9500 . ? C47 H47A 0.9800 . ? C47 H47B 0.9800 . ? C47 H47C 0.9800 . ? C48 H48A 0.9800 . ? C48 H48B 0.9800 . ? C48 H48C 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 O1 S1 O2 119.23(9) . . ? O1 S1 N1 108.69(9) . . ? O2 S1 N1 103.64(8) . . ? O1 S1 C1 107.43(9) . . ? O2 S1 C1 108.47(9) . . ? N1 S1 C1 109.07(9) . . ? O7 S2 O6 119.36(9) . . ? O7 S2 N2 106.23(9) . . ? O6 S2 N2 106.58(9) . . ? O7 S2 C25 107.54(9) . . ? O6 S2 C25 108.96(9) . . ? N2 S2 C25 107.64(10) . . ? C18 O3 H3 109.5 . . ? C20 O4 C23 116.91(15) . . ? C22 O5 C24 118.41(16) . . ? C42 O8 H8 109.5 . . ? C44 O9 C47 116.90(16) . . ? C46 O10 C48 118.16(15) . . ? C8 N1 S1 119.83(13) . . ? C8 N1 H1 117.6(16) . . ? S1 N1 H1 109.3(16) . . ? C32 N2 S2 119.96(13) . . ? C32 N2 H2 114.7(15) . . ? S2 N2 H2 112.2(15) . . ? C6 C1 C2 120.76(19) . . ? C6 C1 S1 119.50(16) . . ? C2 C1 S1 119.71(16) . . ? C3 C2 C1 119.1(2) . . ? C3 C2 H2A 120.4 . . ? C1 C2 H2A 120.4 . . ? C2 C3 C4 121.4(2) . . ? C2 C3 H3A 119.3 . . ? C4 C3 H3A 119.3 . . ? C3 C4 C5 118.7(2) . . ? C3 C4 C7 120.6(2) . . ? C5 C4 C7 120.7(2) . . ? C6 C5 C4 120.7(2) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C1 C6 C5 119.3(2) . . ? C1 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N1 C8 C17 110.97(16) . . ? N1 C8 C9 108.34(16) . . ? C17 C8 C9 116.02(17) . . ? N1 C8 H8A 107.0 . . ? C17 C8 H8A 107.0 . . ? C9 C8 H8A 107.0 . . ? C10 C9 C14 119.04(19) . . ? C10 C9 C8 121.90(18) . . ? C14 C9 C8 119.00(18) . . ? C9 C10 C11 120.70(19) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? C12 C11 C10 118.9(2) . . ? C12 C11 C15 121.2(2) . . ? C10 C11 C15 119.9(2) . . ? C11 C12 C13 121.5(2) . . ? C11 C12 H12 119.2 . . ? C13 C12 H12 119.2 . . ? C14 C13 C12 118.5(2) . . ? C14 C13 C16 120.0(2) . . ? C12 C13 C16 121.5(2) . . ? C13 C14 C9 121.3(2) . . ? C13 C14 H14 119.3 . . ? C9 C14 H14 119.3 . . ? C11 C15 H15A 109.5 . . ? C11 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C11 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 C22 117.42(17) . . ? C18 C17 C8 122.93(18) . . ? C22 C17 C8 119.58(17) . . ? O3 C18 C17 116.60(17) . . ? O3 C18 C19 121.17(17) . . ? C17 C18 C19 122.22(18) . . ? C20 C19 C18 118.56(17) . . ? C20 C19 H19 120.7 . . ? C18 C19 H19 120.7 . . ? O4 C20 C19 123.88(17) . . ? O4 C20 C21 115.28(17) . . ? C19 C20 C21 120.84(18) . . ? C22 C21 C20 119.24(18) . . ? C22 C21 H21 120.4 . . ? C20 C21 H21 120.4 . . ? O5 C22 C21 123.75(17) . . ? O5 C22 C17 114.55(17) . . ? C21 C22 C17 121.68(17) . . ? O4 C23 H23A 109.5 . . ? O4 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O4 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O5 C24 H24A 109.5 . . ? O5 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O5 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C26 C25 C30 120.8(2) . . ? C26 C25 S2 118.21(16) . . ? C30 C25 S2 120.89(16) . . ? C25 C26 C27 119.7(2) . . ? C25 C26 H26 120.1 . . ? C27 C26 H26 120.1 . . ? C26 C27 C28 121.2(2) . . ? C26 C27 H27 119.4 . . ? C28 C27 H27 119.4 . . ? C29 C28 C27 117.5(2) . . ? C29 C28 C31 121.9(2) . . ? C27 C28 C31 120.6(2) . . ? C30 C29 C28 122.4(2) . . ? C30 C29 H29 118.8 . . ? C28 C29 H29 118.8 . . ? C29 C30 C25 118.4(2) . . ? C29 C30 H30 120.8 . . ? C25 C30 H30 120.8 . . ? C28 C31 H31A 109.5 . . ? C28 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C28 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? N2 C32 C41 115.36(16) . . ? N2 C32 C33 108.04(15) . . ? C41 C32 C33 115.37(18) . . ? N2 C32 H32 105.7 . . ? C41 C32 H32 105.7 . . ? C33 C32 H32 105.7 . . ? C34 C33 C38 118.91(19) . . ? C34 C33 C32 121.56(19) . . ? C38 C33 C32 119.45(19) . . ? C33 C34 C35 121.0(2) . . ? C33 C34 H34 119.5 . . ? C35 C34 H34 119.5 . . ? C36 C35 C34 118.5(2) . . ? C36 C35 C39 121.3(2) . . ? C34 C35 C39 120.2(2) . . ? C35 C36 C37 122.0(2) . . ? C35 C36 H36 119.0 . . ? C37 C36 H36 119.0 . . ? C38 C37 C36 118.1(2) . . ? C38 C37 C40 119.9(2) . . ? C36 C37 C40 122.0(2) . . ? C37 C38 C33 121.4(2) . . ? C37 C38 H38 119.3 . . ? C33 C38 H38 119.3 . . ? C35 C39 H39A 109.5 . . ? C35 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C35 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C37 C40 H40A 109.5 . . ? C37 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C37 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? C42 C41 C46 116.78(18) . . ? C42 C41 C32 119.24(18) . . ? C46 C41 C32 123.95(18) . . ? O8 C42 C43 121.15(18) . . ? O8 C42 C41 116.17(18) . . ? C43 C42 C41 122.68(18) . . ? C44 C43 C42 118.50(18) . . ? C44 C43 H43 120.8 . . ? C42 C43 H43 120.8 . . ? O9 C44 C43 123.86(18) . . ? O9 C44 C45 114.90(18) . . ? C43 C44 C45 121.23(19) . . ? C46 C45 C44 118.90(19) . . ? C46 C45 H45 120.5 . . ? C44 C45 H45 120.5 . . ? O10 C46 C45 123.21(17) . . ? O10 C46 C41 114.90(17) . . ? C45 C46 C41 121.88(18) . . ? O9 C47 H47A 109.5 . . ? O9 C47 H47B 109.5 . . ? H47A C47 H47B 109.5 . . ? O9 C47 H47C 109.5 . . ? H47A C47 H47C 109.5 . . ? H47B C47 H47C 109.5 . . ? O10 C48 H48A 109.5 . . ? O10 C48 H48B 109.5 . . ? H48A C48 H48B 109.5 . . ? O10 C48 H48C 109.5 . . ? H48A C48 H48C 109.5 . . ? H48B C48 H48C 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 O1 S1 N1 C8 60.32(16) . . . . ? O2 S1 N1 C8 -171.91(14) . . . . ? C1 S1 N1 C8 -56.52(17) . . . . ? O7 S2 N2 C32 169.16(14) . . . . ? O6 S2 N2 C32 40.88(16) . . . . ? C25 S2 N2 C32 -75.88(16) . . . . ? O1 S1 C1 C6 159.79(17) . . . . ? O2 S1 C1 C6 29.67(19) . . . . ? N1 S1 C1 C6 -82.57(19) . . . . ? O1 S1 C1 C2 -22.2(2) . . . . ? O2 S1 C1 C2 -152.35(17) . . . . ? N1 S1 C1 C2 95.41(18) . . . . ? C6 C1 C2 C3 -1.3(3) . . . . ? S1 C1 C2 C3 -179.27(18) . . . . ? C1 C2 C3 C4 0.1(4) . . . . ? C2 C3 C4 C5 0.6(4) . . . . ? C2 C3 C4 C7 -178.2(2) . . . . ? C3 C4 C5 C6 0.1(4) . . . . ? C7 C4 C5 C6 178.8(2) . . . . ? C2 C1 C6 C5 1.9(3) . . . . ? S1 C1 C6 C5 179.87(18) . . . . ? C4 C5 C6 C1 -1.3(4) . . . . ? S1 N1 C8 C17 94.94(17) . . . . ? S1 N1 C8 C9 -136.59(15) . . . . ? N1 C8 C9 C10 -137.62(19) . . . . ? C17 C8 C9 C10 -12.1(3) . . . . ? N1 C8 C9 C14 45.3(2) . . . . ? C17 C8 C9 C14 170.83(17) . . . . ? C14 C9 C10 C11 -0.5(3) . . . . ? C8 C9 C10 C11 -177.55(18) . . . . ? C9 C10 C11 C12 -1.3(3) . . . . ? C9 C10 C11 C15 178.6(2) . . . . ? C10 C11 C12 C13 1.8(3) . . . . ? C15 C11 C12 C13 -178.1(2) . . . . ? C11 C12 C13 C14 -0.5(3) . . . . ? C11 C12 C13 C16 -178.8(2) . . . . ? C12 C13 C14 C9 -1.3(3) . . . . ? C16 C13 C14 C9 177.0(2) . . . . ? C10 C9 C14 C13 1.8(3) . . . . ? C8 C9 C14 C13 178.96(18) . . . . ? N1 C8 C17 C18 44.5(2) . . . . ? C9 C8 C17 C18 -79.7(2) . . . . ? N1 C8 C17 C22 -132.39(18) . . . . ? C9 C8 C17 C22 103.4(2) . . . . ? C22 C17 C18 O3 -179.04(17) . . . . ? C8 C17 C18 O3 4.0(3) . . . . ? C22 C17 C18 C19 2.2(3) . . . . ? C8 C17 C18 C19 -174.70(19) . . . . ? O3 C18 C19 C20 179.23(18) . . . . ? C17 C18 C19 C20 -2.1(3) . . . . ? C23 O4 C20 C19 16.3(3) . . . . ? C23 O4 C20 C21 -163.69(17) . . . . ? C18 C19 C20 O4 -179.16(18) . . . . ? C18 C19 C20 C21 0.8(3) . . . . ? O4 C20 C21 C22 -179.73(19) . . . . ? C19 C20 C21 C22 0.3(3) . . . . ? C24 O5 C22 C21 -4.8(3) . . . . ? C24 O5 C22 C17 176.55(19) . . . . ? C20 C21 C22 O5 -178.70(18) . . . . ? C20 C21 C22 C17 -0.2(3) . . . . ? C18 C17 C22 O5 177.58(17) . . . . ? C8 C17 C22 O5 -5.4(3) . . . . ? C18 C17 C22 C21 -1.1(3) . . . . ? C8 C17 C22 C21 175.97(19) . . . . ? O7 S2 C25 C26 39.5(2) . . . . ? O6 S2 C25 C26 170.23(18) . . . . ? N2 S2 C25 C26 -74.6(2) . . . . ? O7 S2 C25 C30 -143.80(19) . . . . ? O6 S2 C25 C30 -13.1(2) . . . . ? N2 S2 C25 C30 102.11(19) . . . . ? C30 C25 C26 C27 0.6(4) . . . . ? S2 C25 C26 C27 177.2(2) . . . . ? C25 C26 C27 C28 1.1(4) . . . . ? C26 C27 C28 C29 -2.0(4) . . . . ? C26 C27 C28 C31 177.1(3) . . . . ? C27 C28 C29 C30 1.2(4) . . . . ? C31 C28 C29 C30 -177.9(3) . . . . ? C28 C29 C30 C25 0.4(4) . . . . ? C26 C25 C30 C29 -1.3(4) . . . . ? S2 C25 C30 C29 -177.91(19) . . . . ? S2 N2 C32 C41 78.7(2) . . . . ? S2 N2 C32 C33 -150.58(14) . . . . ? N2 C32 C33 C34 -141.90(19) . . . . ? C41 C32 C33 C34 -11.1(3) . . . . ? N2 C32 C33 C38 41.6(2) . . . . ? C41 C32 C33 C38 172.31(17) . . . . ? C38 C33 C34 C35 -0.4(3) . . . . ? C32 C33 C34 C35 -176.93(18) . . . . ? C33 C34 C35 C36 0.8(3) . . . . ? C33 C34 C35 C39 -177.6(2) . . . . ? C34 C35 C36 C37 -0.3(3) . . . . ? C39 C35 C36 C37 178.2(2) . . . . ? C35 C36 C37 C38 -0.8(3) . . . . ? C35 C36 C37 C40 179.8(2) . . . . ? C36 C37 C38 C33 1.3(3) . . . . ? C40 C37 C38 C33 -179.3(2) . . . . ? C34 C33 C38 C37 -0.7(3) . . . . ? C32 C33 C38 C37 175.91(18) . . . . ? N2 C32 C41 C42 -137.55(19) . . . . ? C33 C32 C41 C42 95.3(2) . . . . ? N2 C32 C41 C46 44.4(3) . . . . ? C33 C32 C41 C46 -82.8(2) . . . . ? C46 C41 C42 O8 177.63(18) . . . . ? C32 C41 C42 O8 -0.6(3) . . . . ? C46 C41 C42 C43 -2.0(3) . . . . ? C32 C41 C42 C43 179.75(19) . . . . ? O8 C42 C43 C44 -178.68(19) . . . . ? C41 C42 C43 C44 1.0(3) . . . . ? C47 O9 C44 C43 -15.8(3) . . . . ? C47 O9 C44 C45 163.37(18) . . . . ? C42 C43 C44 O9 179.47(19) . . . . ? C42 C43 C44 C45 0.4(3) . . . . ? O9 C44 C45 C46 -179.71(18) . . . . ? C43 C44 C45 C46 -0.5(3) . . . . ? C48 O10 C46 C45 3.4(3) . . . . ? C48 O10 C46 C41 -177.31(18) . . . . ? C44 C45 C46 O10 178.66(18) . . . . ? C44 C45 C46 C41 -0.6(3) . . . . ? C42 C41 C46 O10 -177.50(17) . . . . ? C32 C41 C46 O10 0.6(3) . . . . ? C42 C41 C46 C45 1.8(3) . . . . ? C32 C41 C46 C45 179.97(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 O3 H3 O2 0.84 1.95 2.763(2) 163.6 2_556 O8 H8 O6 0.84 1.94 2.776(2) 171.2 2_647 N1 H1 O3 0.901(9) 2.11(2) 2.726(2) 125(2) . N2 H2 O10 0.895(9) 2.22(2) 2.772(2) 119.5(18) . N2 H2 O1 0.895(9) 2.597(14) 3.399(2) 150(2) 1_565 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.89 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.291 _refine_diff_density_min -0.360 _refine_diff_density_rms 0.053 # Attachment 'web_deposit_cif_file_1_Guo-XingLi_1313051034.shelx.cif' data_shelx2 _database_code_depnum_ccdc_archive 'CCDC 838867' #TrackingRef 'web_deposit_cif_file_1_Guo-XingLi_1313051034.shelx.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H22 F N O5 S' _chemical_formula_weight 431.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.745(3) _cell_length_b 11.871(3) _cell_length_c 18.087(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2092.4(9) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 7314 _cell_measurement_theta_min 1.7 _cell_measurement_theta_max 27.9 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.370 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 0.197 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9616 _exptl_absorpt_correction_T_max 0.9767 _exptl_absorpt_process_details CrystalClear _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator multilayer _diffrn_measurement_device_type 'Rigaku Saturn724 CCD' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean 14.22 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 24105 _diffrn_reflns_av_R_equivalents 0.0485 _diffrn_reflns_av_sigmaI/netI 0.0492 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 27.90 _reflns_number_total 4988 _reflns_number_gt 4325 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'CrystalStructure 3.8' _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^)+(0.0325P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.05(5) _refine_ls_number_reflns 4988 _refine_ls_number_parameters 279 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0394 _refine_ls_R_factor_gt 0.0337 _refine_ls_wR_factor_ref 0.0700 _refine_ls_wR_factor_gt 0.0679 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _refine_ls_shift/su_max 0.001 _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 0.25088(4) 0.58592(3) 0.83797(2) 0.02169(9) Uani 1 1 d . . . F1 F 0.16274(12) 0.54654(9) 0.62129(6) 0.0470(3) Uani 1 1 d . . . O1 O 0.11267(13) 0.55433(9) 0.81880(6) 0.0316(3) Uani 1 1 d . . . O2 O 0.34050(12) 0.50409(9) 0.87075(6) 0.0274(3) Uani 1 1 d . . . O3 O 0.06492(11) 0.87218(9) 0.69380(6) 0.0255(3) Uani 1 1 d . . . H3 H 0.0097 0.9257 0.6878 0.038 Uiso 1 1 calc R . . O4 O 0.50406(11) 0.79541(9) 0.78936(6) 0.0237(3) Uani 1 1 d . . . O5 O 0.30559(12) 1.15328(9) 0.83563(7) 0.0323(3) Uani 1 1 d . . . N1 N 0.32505(15) 0.62494(11) 0.76201(7) 0.0204(3) Uani 1 1 d D . . C1 C 0.23712(17) 0.70196(12) 0.89853(8) 0.0211(3) Uani 1 1 d . . . C2 C 0.12726(17) 0.77571(14) 0.89142(8) 0.0239(4) Uani 1 1 d . . . H2 H 0.0571 0.7616 0.8562 0.029 Uiso 1 1 calc R . . C3 C 0.12131(19) 0.87031(14) 0.93649(9) 0.0284(4) Uani 1 1 d . . . H3A H 0.0467 0.9213 0.9314 0.034 Uiso 1 1 calc R . . C4 C 0.22258(19) 0.89191(14) 0.98894(9) 0.0296(4) Uani 1 1 d . . . C5 C 0.3309(2) 0.81648(14) 0.99491(9) 0.0298(4) Uani 1 1 d . . . H5 H 0.4007 0.8299 1.0305 0.036 Uiso 1 1 calc R . . C6 C 0.33942(18) 0.72218(14) 0.95008(8) 0.0250(4) Uani 1 1 d . . . H6 H 0.4147 0.6718 0.9546 0.030 Uiso 1 1 calc R . . C7 C 0.2147(2) 0.99579(17) 1.03714(11) 0.0483(6) Uani 1 1 d . . . H7A H 0.2360 1.0626 1.0074 0.072 Uiso 1 1 calc R . . H7B H 0.2812 0.9893 1.0776 0.072 Uiso 1 1 calc R . . H7C H 0.1220 1.0028 1.0576 0.072 Uiso 1 1 calc R . . C8 C 0.26540(17) 0.71430(12) 0.71427(7) 0.0190(3) Uani 1 1 d . . . H8 H 0.1644 0.6999 0.7118 0.023 Uiso 1 1 calc R . . C9 C 0.28348(15) 0.83331(12) 0.74233(8) 0.0172(3) Uani 1 1 d . . . C10 C 0.17734(16) 0.90951(13) 0.73272(8) 0.0185(3) Uani 1 1 d . . . C11 C 0.17940(17) 1.01799(13) 0.76221(8) 0.0204(3) Uani 1 1 d . . . H11 H 0.1048 1.0682 0.7547 0.025 Uiso 1 1 calc R . . C12 C 0.29240(16) 1.05024(13) 0.80255(9) 0.0217(4) Uani 1 1 d . . . C13 C 0.40311(17) 0.97806(13) 0.81264(8) 0.0220(4) Uani 1 1 d . . . H13 H 0.4810 1.0018 0.8401 0.026 Uiso 1 1 calc R . . C14 C 0.39858(16) 0.87175(13) 0.78230(8) 0.0197(3) Uani 1 1 d . . . C15 C 0.62148(17) 0.82855(15) 0.83137(10) 0.0327(4) Uani 1 1 d . . . H15A H 0.5936 0.8454 0.8822 0.049 Uiso 1 1 calc R . . H15B H 0.6626 0.8958 0.8091 0.049 Uiso 1 1 calc R . . H15C H 0.6887 0.7672 0.8316 0.049 Uiso 1 1 calc R . . C16 C 0.1906(2) 1.22715(14) 0.83276(10) 0.0353(4) Uani 1 1 d . . . H16A H 0.1117 1.1912 0.8566 0.053 Uiso 1 1 calc R . . H16B H 0.1683 1.2437 0.7811 0.053 Uiso 1 1 calc R . . H16C H 0.2128 1.2974 0.8586 0.053 Uiso 1 1 calc R . . C17 C 0.32225(18) 0.69400(13) 0.63684(8) 0.0223(4) Uani 1 1 d . . . C18 C 0.43028(18) 0.75535(15) 0.60739(9) 0.0286(4) Uani 1 1 d . . . H18 H 0.4682 0.8162 0.6347 0.034 Uiso 1 1 calc R . . C19 C 0.4838(2) 0.72856(18) 0.53819(9) 0.0413(5) Uani 1 1 d . . . H19 H 0.5576 0.7714 0.5185 0.050 Uiso 1 1 calc R . . C20 C 0.4304(3) 0.6404(2) 0.49828(10) 0.0526(7) Uani 1 1 d . . . H20 H 0.4689 0.6215 0.4516 0.063 Uiso 1 1 calc R . . C21 C 0.3211(2) 0.57898(18) 0.52565(10) 0.0474(6) Uani 1 1 d . . . H21 H 0.2819 0.5190 0.4980 0.057 Uiso 1 1 calc R . . C22 C 0.2708(2) 0.60756(14) 0.59419(9) 0.0334(4) Uani 1 1 d . . . H1 H 0.4140(10) 0.6363(13) 0.7716(8) 0.017(4) Uiso 1 1 d 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 S1 0.0262(2) 0.01705(17) 0.02177(18) 0.00187(15) -0.00190(18) -0.00319(19) F1 0.0538(8) 0.0380(6) 0.0492(7) -0.0158(5) -0.0164(6) -0.0074(6) O1 0.0288(7) 0.0278(6) 0.0383(7) 0.0002(5) -0.0038(5) -0.0112(6) O2 0.0372(8) 0.0192(6) 0.0259(6) 0.0061(5) -0.0025(5) 0.0023(6) O3 0.0239(7) 0.0202(6) 0.0324(6) -0.0039(5) -0.0112(5) 0.0033(5) O4 0.0180(6) 0.0217(6) 0.0314(6) -0.0022(5) -0.0041(5) 0.0027(5) O5 0.0325(7) 0.0182(6) 0.0460(7) -0.0113(5) -0.0084(6) 0.0006(5) N1 0.0225(8) 0.0189(7) 0.0198(7) 0.0011(5) -0.0025(6) 0.0020(6) C1 0.0249(9) 0.0209(8) 0.0174(7) 0.0027(6) 0.0015(7) -0.0033(8) C2 0.0206(9) 0.0295(9) 0.0216(8) 0.0046(7) 0.0014(7) 0.0000(7) C3 0.0295(10) 0.0287(9) 0.0270(9) 0.0044(7) 0.0089(8) 0.0078(8) C4 0.0366(12) 0.0281(10) 0.0242(8) -0.0031(7) 0.0061(7) 0.0003(8) C5 0.0324(11) 0.0345(10) 0.0226(8) -0.0038(7) -0.0051(8) -0.0028(9) C6 0.0258(10) 0.0255(9) 0.0238(8) 0.0017(7) -0.0033(7) 0.0021(7) C7 0.0588(16) 0.0400(11) 0.0461(11) -0.0173(9) 0.0063(10) 0.0042(11) C8 0.0226(9) 0.0164(7) 0.0179(7) 0.0000(6) -0.0047(7) 0.0025(7) C9 0.0202(9) 0.0166(7) 0.0147(7) 0.0001(6) 0.0014(6) -0.0018(6) C10 0.0193(8) 0.0198(8) 0.0162(7) -0.0002(6) -0.0022(6) -0.0012(7) C11 0.0199(8) 0.0161(8) 0.0253(8) 0.0020(6) -0.0011(7) 0.0016(7) C12 0.0248(10) 0.0160(8) 0.0243(8) -0.0019(6) 0.0026(7) -0.0027(6) C13 0.0195(9) 0.0217(9) 0.0248(8) -0.0011(7) -0.0022(7) -0.0040(7) C14 0.0167(9) 0.0201(8) 0.0225(8) 0.0043(7) 0.0014(6) 0.0002(7) C15 0.0196(9) 0.0332(10) 0.0454(11) 0.0028(9) -0.0095(8) -0.0002(8) C16 0.0391(11) 0.0192(9) 0.0477(11) -0.0107(8) 0.0016(9) 0.0042(8) C17 0.0270(9) 0.0222(9) 0.0177(7) -0.0003(6) -0.0049(7) 0.0103(7) C18 0.0340(11) 0.0295(9) 0.0223(8) 0.0057(7) -0.0002(7) 0.0110(8) C19 0.0448(12) 0.0560(13) 0.0230(9) 0.0104(9) 0.0051(8) 0.0219(11) C20 0.0738(17) 0.0692(16) 0.0149(9) -0.0009(10) -0.0015(10) 0.0407(14) C21 0.0664(15) 0.0494(13) 0.0264(10) -0.0156(9) -0.0174(10) 0.0216(13) C22 0.0417(12) 0.0320(10) 0.0264(9) -0.0059(7) -0.0101(8) 0.0101(9) _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 O2 1.4345(11) . ? S1 O1 1.4405(13) . ? S1 N1 1.6200(14) . ? S1 C1 1.7650(16) . ? F1 C22 1.369(2) . ? O3 C10 1.3756(18) . ? O3 H3 0.8400 . ? O4 C14 1.3763(18) . ? O4 C15 1.4287(19) . ? O5 C12 1.3677(18) . ? O5 C16 1.424(2) . ? N1 C8 1.4862(18) . ? N1 H1 0.894(9) . ? C1 C6 1.386(2) . ? C1 C2 1.389(2) . ? C2 C3 1.389(2) . ? C2 H2 0.9500 . ? C3 C4 1.393(2) . ? C3 H3A 0.9500 . ? C4 C5 1.389(2) . ? C4 C7 1.512(2) . ? C5 C6 1.385(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C9 1.511(2) . ? C8 C17 1.525(2) . ? C8 H8 1.0000 . ? C9 C10 1.385(2) . ? C9 C14 1.410(2) . ? C10 C11 1.394(2) . ? C11 C12 1.375(2) . ? C11 H11 0.9500 . ? C12 C13 1.390(2) . ? C13 C14 1.377(2) . ? C13 H13 0.9500 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C22 1.378(2) . ? C17 C18 1.386(2) . ? C18 C19 1.393(2) . ? C18 H18 0.9500 . ? C19 C20 1.374(3) . ? C19 H19 0.9500 . ? C20 C21 1.383(3) . ? C20 H20 0.9500 . ? C21 C22 1.375(3) . ? C21 H21 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 O2 S1 O1 119.50(7) . . ? O2 S1 N1 105.81(7) . . ? O1 S1 N1 106.71(7) . . ? O2 S1 C1 108.56(7) . . ? O1 S1 C1 106.35(8) . . ? N1 S1 C1 109.70(7) . . ? C10 O3 H3 109.5 . . ? C14 O4 C15 117.79(12) . . ? C12 O5 C16 117.45(13) . . ? C8 N1 S1 121.48(11) . . ? C8 N1 H1 112.6(10) . . ? S1 N1 H1 108.1(9) . . ? C6 C1 C2 120.50(14) . . ? C6 C1 S1 119.87(12) . . ? C2 C1 S1 119.54(12) . . ? C3 C2 C1 119.18(15) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C2 C3 C4 121.27(16) . . ? C2 C3 H3A 119.4 . . ? C4 C3 H3A 119.4 . . ? C5 C4 C3 118.23(15) . . ? C5 C4 C7 121.30(16) . . ? C3 C4 C7 120.47(17) . . ? C6 C5 C4 121.42(16) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C5 C6 C1 119.40(16) . . ? C5 C6 H6 120.3 . . ? C1 C6 H6 120.3 . . ? C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N1 C8 C9 115.25(12) . . ? N1 C8 C17 106.17(12) . . ? C9 C8 C17 114.43(13) . . ? N1 C8 H8 106.8 . . ? C9 C8 H8 106.8 . . ? C17 C8 H8 106.8 . . ? C10 C9 C14 116.54(13) . . ? C10 C9 C8 118.77(13) . . ? C14 C9 C8 124.56(14) . . ? O3 C10 C9 116.65(13) . . ? O3 C10 C11 120.32(14) . . ? C9 C10 C11 123.00(14) . . ? C12 C11 C10 118.14(15) . . ? C12 C11 H11 120.9 . . ? C10 C11 H11 120.9 . . ? O5 C12 C11 123.80(14) . . ? O5 C12 C13 114.90(14) . . ? C11 C12 C13 121.30(14) . . ? C14 C13 C12 119.21(15) . . ? C14 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? O4 C14 C13 122.87(14) . . ? O4 C14 C9 115.37(13) . . ? C13 C14 C9 121.76(15) . . ? O4 C15 H15A 109.5 . . ? O4 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O4 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O5 C16 H16A 109.5 . . ? O5 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O5 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C22 C17 C18 116.90(15) . . ? C22 C17 C8 119.96(16) . . ? C18 C17 C8 123.06(15) . . ? C17 C18 C19 120.64(18) . . ? C17 C18 H18 119.7 . . ? C19 C18 H18 119.7 . . ? C20 C19 C18 120.3(2) . . ? C20 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? C19 C20 C21 120.36(18) . . ? C19 C20 H20 119.8 . . ? C21 C20 H20 119.8 . . ? C22 C21 C20 117.85(19) . . ? C22 C21 H21 121.1 . . ? C20 C21 H21 121.1 . . ? F1 C22 C21 117.78(17) . . ? F1 C22 C17 118.26(15) . . ? C21 C22 C17 123.96(19) . . ? 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 O2 S1 N1 C8 -176.85(11) . . . . ? O1 S1 N1 C8 54.88(13) . . . . ? C1 S1 N1 C8 -59.93(13) . . . . ? O2 S1 C1 C6 22.92(15) . . . . ? O1 S1 C1 C6 152.70(12) . . . . ? N1 S1 C1 C6 -92.26(13) . . . . ? O2 S1 C1 C2 -160.50(11) . . . . ? O1 S1 C1 C2 -30.72(14) . . . . ? N1 S1 C1 C2 84.32(14) . . . . ? C6 C1 C2 C3 0.2(2) . . . . ? S1 C1 C2 C3 -176.36(12) . . . . ? C1 C2 C3 C4 -0.6(2) . . . . ? C2 C3 C4 C5 0.4(2) . . . . ? C2 C3 C4 C7 179.60(16) . . . . ? C3 C4 C5 C6 0.2(3) . . . . ? C7 C4 C5 C6 -179.03(16) . . . . ? C4 C5 C6 C1 -0.6(2) . . . . ? C2 C1 C6 C5 0.4(2) . . . . ? S1 C1 C6 C5 176.90(12) . . . . ? S1 N1 C8 C9 75.88(17) . . . . ? S1 N1 C8 C17 -156.32(12) . . . . ? N1 C8 C9 C10 -142.13(14) . . . . ? C17 C8 C9 C10 94.33(17) . . . . ? N1 C8 C9 C14 33.7(2) . . . . ? C17 C8 C9 C14 -89.88(17) . . . . ? C14 C9 C10 O3 -179.95(13) . . . . ? C8 C9 C10 O3 -3.8(2) . . . . ? C14 C9 C10 C11 -1.9(2) . . . . ? C8 C9 C10 C11 174.28(14) . . . . ? O3 C10 C11 C12 178.10(14) . . . . ? C9 C10 C11 C12 0.1(2) . . . . ? C16 O5 C12 C11 5.2(2) . . . . ? C16 O5 C12 C13 -174.61(14) . . . . ? C10 C11 C12 O5 -178.54(14) . . . . ? C10 C11 C12 C13 1.3(2) . . . . ? O5 C12 C13 C14 179.09(14) . . . . ? C11 C12 C13 C14 -0.8(2) . . . . ? C15 O4 C14 C13 1.2(2) . . . . ? C15 O4 C14 C9 -178.03(13) . . . . ? C12 C13 C14 O4 179.64(14) . . . . ? C12 C13 C14 C9 -1.2(2) . . . . ? C10 C9 C14 O4 -178.34(12) . . . . ? C8 C9 C14 O4 5.8(2) . . . . ? C10 C9 C14 C13 2.4(2) . . . . ? C8 C9 C14 C13 -173.49(14) . . . . ? N1 C8 C17 C22 75.87(18) . . . . ? C9 C8 C17 C22 -155.85(15) . . . . ? N1 C8 C17 C18 -100.67(17) . . . . ? C9 C8 C17 C18 27.6(2) . . . . ? C22 C17 C18 C19 -0.7(2) . . . . ? C8 C17 C18 C19 175.91(15) . . . . ? C17 C18 C19 C20 -0.3(3) . . . . ? C18 C19 C20 C21 1.5(3) . . . . ? C19 C20 C21 C22 -1.5(3) . . . . ? C20 C21 C22 F1 -179.84(16) . . . . ? C20 C21 C22 C17 0.5(3) . . . . ? C18 C17 C22 F1 -179.03(14) . . . . ? C8 C17 C22 F1 4.2(2) . . . . ? C18 C17 C22 C21 0.7(2) . . . . ? C8 C17 C22 C21 -176.09(16) . . . . ? 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 O3 H3 O1 0.84 1.94 2.7789(16) 175.5 3_556 N1 H1 O4 0.894(9) 2.107(13) 2.7172(18) 124.7(13) . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.90 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.187 _refine_diff_density_min -0.303 _refine_diff_density_rms 0.048