# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Rita Delgado' _publ_contact_author_email DELGADO@ITQB.UNL.PT _publ_section_title ; Selective Recognition of Tetrahedral Dianions by a Hexaaza Cryptand Receptor ; loop_ _publ_author_name 'Rita Delgado' 'Paula Brandao' 'Silvia Carvalho' 'Vitor Felix' 'Pedro Mateus' # Attachment 'B912940E_cif.cif' data_referee _database_code_depnum_ccdc_archive 'CCDC 734450' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C54 H109 N6 O27.50 S3' _chemical_formula_weight 1378.65 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.5490(5) _cell_length_b 15.0384(6) _cell_length_c 19.0959(7) _cell_angle_alpha 99.510(2) _cell_angle_beta 99.578(2) _cell_angle_gamma 98.598(2) _cell_volume 3446.1(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour clourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.329 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1486 _exptl_absorpt_coefficient_mu 0.191 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9627 _exptl_absorpt_correction_T_max 0.9924 _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CCD _diffrn_measurement_method 'omega phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count 0.5 _diffrn_standards_interval_time 120 _diffrn_standards_decay_% ? _diffrn_reflns_number 55623 _diffrn_reflns_av_R_equivalents 0.0365 _diffrn_reflns_av_sigmaI/netI 0.0425 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 29.12 _reflns_number_total 16070 _reflns_number_gt 10951 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PYMOL (DeLano Scientific LLC 2008)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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 w=1/[\s^2^(Fo^2^)+(0.1362P)^2^+4.6118P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 16070 _refine_ls_number_parameters 935 _refine_ls_number_restraints 20 _refine_ls_R_factor_all 0.1114 _refine_ls_R_factor_gt 0.0761 _refine_ls_wR_factor_ref 0.2510 _refine_ls_wR_factor_gt 0.2188 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.7660(3) 0.1517(2) -0.01721(16) 0.0453(8) Uani 1 d . . . H1A H 0.8157 0.1227 -0.0381 0.054 Uiso 1 calc R . . H1B H 0.7912 0.1644 0.0321 0.054 Uiso 1 calc R . . N2 N 0.6540(2) -0.28138(18) -0.08803(15) 0.0295(6) Uani 1 d . . . H2A H 0.5874 -0.2822 -0.0738 0.035 Uiso 1 calc R . . H2B H 0.6532 -0.2493 -0.1251 0.035 Uiso 1 calc R . . N3 N 0.4866(2) -0.2849(2) -0.37273(16) 0.0355(6) Uani 1 d . . . H3A H 0.4485 -0.2687 -0.3368 0.043 Uiso 1 calc R . . H3B H 0.5548 -0.2478 -0.3609 0.043 Uiso 1 calc R . . N4 N 0.5072(2) 0.1348(2) -0.32883(16) 0.0349(7) Uani 1 d . . . H4A H 0.5093 0.1038 -0.2911 0.042 Uiso 1 calc R . . H4B H 0.4357 0.1418 -0.3430 0.042 Uiso 1 calc R . . N5 N 1.0117(2) 0.15622(18) -0.27272(15) 0.0294(6) Uani 1 d . . . H5A H 0.9468 0.1209 -0.2992 0.035 Uiso 1 calc R . . H5B H 1.0579 0.1664 -0.3044 0.035 Uiso 1 calc R . . N6 N 0.9684(2) -0.28368(18) -0.27952(14) 0.0295(6) Uani 1 d . . . H6A H 0.9392 -0.2538 -0.2433 0.035 Uiso 1 calc R . . H6B H 1.0405 -0.2844 -0.2604 0.035 Uiso 1 calc R . . C1 C 0.6586(4) 0.0881(3) -0.0338(2) 0.0492(11) Uani 1 d . . . H1C H 0.6368 0.0650 -0.0867 0.059 Uiso 1 calc R . . H1D H 0.6016 0.1212 -0.0181 0.059 Uiso 1 calc R . . C2 C 0.6665(4) 0.0080(2) 0.00468(19) 0.0450(10) Uani 1 d . . . C3 C 0.6360(3) 0.0131(2) 0.07183(18) 0.0385(8) Uani 1 d . . . H3 H 0.6132 0.0666 0.0937 0.046 Uiso 1 calc R . . C4 C 0.6394(3) -0.0612(3) 0.10670(19) 0.0411(9) Uani 1 d . . . H4 H 0.6173 -0.0586 0.1521 0.049 Uiso 1 calc R . . C5 C 0.6745(4) -0.1386(3) 0.0758(2) 0.0454(9) Uani 1 d . . . H5 H 0.6754 -0.1889 0.0999 0.055 Uiso 1 calc R . . C6 C 0.7086(3) -0.1436(3) 0.0094(2) 0.0394(8) Uani 1 d . . . C7 C 0.7040(3) -0.0699(3) -0.02568(19) 0.0411(9) Uani 1 d . . . H7 H 0.7266 -0.0724 -0.0709 0.049 Uiso 1 calc R . . C8 C 0.7435(3) -0.2293(3) -0.0249(2) 0.0433(9) Uani 1 d . . . H8A H 0.7571 -0.2685 0.0113 0.052 Uiso 1 calc R . . H8B H 0.8126 -0.2129 -0.0422 0.052 Uiso 1 calc R . . C9 C 0.6634(3) -0.3792(2) -0.11753(19) 0.0330(7) Uani 1 d . . . H9A H 0.7279 -0.3955 -0.0883 0.040 Uiso 1 calc R . . H9B H 0.5970 -0.4214 -0.1138 0.040 Uiso 1 calc R . . C10 C 0.6758(3) -0.3899(2) -0.19578(18) 0.0285(7) Uani 1 d . . . C11 C 0.5843(3) -0.3918(2) -0.24958(19) 0.0320(7) Uani 1 d . . . C12 C 0.4712(3) -0.3931(2) -0.2298(2) 0.0384(8) Uani 1 d . . . H12A H 0.4802 -0.3587 -0.1797 0.046 Uiso 1 calc R . . H12B H 0.4273 -0.3615 -0.2624 0.046 Uiso 1 calc R . . C13 C 0.4089(4) -0.4896(3) -0.2353(3) 0.0603(13) Uani 1 d . . . H13A H 0.4012 -0.5245 -0.2845 0.072 Uiso 1 calc R . . H13B H 0.3358 -0.4864 -0.2242 0.072 Uiso 1 calc R . . H13C H 0.4494 -0.5199 -0.2007 0.072 Uiso 1 calc R . . C14 C 0.5976(3) -0.3914(2) -0.32082(18) 0.0320(7) Uani 1 d . . . C15 C 0.5000(3) -0.3838(3) -0.3768(2) 0.0395(8) Uani 1 d . . . H15A H 0.5108 -0.4094 -0.4258 0.047 Uiso 1 calc R . . H15B H 0.4325 -0.4201 -0.3683 0.047 Uiso 1 calc R . . C16 C 0.4271(3) -0.2704(3) -0.44232(19) 0.0446(9) Uani 1 d . . . H16A H 0.3570 -0.3149 -0.4569 0.054 Uiso 1 calc R . . H16B H 0.4715 -0.2836 -0.4798 0.054 Uiso 1 calc R . . C17 C 0.4024(3) -0.1751(3) -0.44069(17) 0.0367(8) Uani 1 d . . . C18 C 0.2984(3) -0.1679(3) -0.47369(19) 0.0440(10) Uani 1 d . . . H18 H 0.2434 -0.2215 -0.4903 0.053 Uiso 1 calc R . . C19 C 0.2732(3) -0.0843(3) -0.4829(2) 0.0567(13) Uani 1 d . . . H19 H 0.2021 -0.0804 -0.5073 0.068 Uiso 1 calc R . . C20 C 0.3526(3) -0.0052(3) -0.4564(2) 0.0538(12) Uani 1 d . . . H20 H 0.3356 0.0526 -0.4633 0.065 Uiso 1 calc R . . C21 C 0.4563(3) -0.0102(3) -0.41981(18) 0.0350(8) Uani 1 d . . . C22 C 0.4817(3) -0.0951(3) -0.41286(17) 0.0344(8) Uani 1 d . . . H22 H 0.5531 -0.0993 -0.3892 0.041 Uiso 1 calc R . . C23 C 0.5398(3) 0.0775(2) -0.39057(17) 0.0321(7) Uani 1 d . . . H23A H 0.6127 0.0622 -0.3741 0.039 Uiso 1 calc R . . H23B H 0.5457 0.1127 -0.4296 0.039 Uiso 1 calc R . . C24 C 0.5781(3) 0.2292(2) -0.30138(19) 0.0338(7) Uani 1 d . . . H24A H 0.5996 0.2535 -0.3431 0.041 Uiso 1 calc R . . H24B H 0.5338 0.2708 -0.2788 0.041 Uiso 1 calc R . . C25 C 0.6809(3) 0.2302(2) -0.24684(17) 0.0298(7) Uani 1 d . . . C26 C 0.6728(3) 0.2306(2) -0.17404(19) 0.0342(8) Uani 1 d . . . C27 C 0.5632(4) 0.2377(3) -0.1520(2) 0.0431(9) Uani 1 d . . . H27A H 0.5570 0.2073 -0.1103 0.052 Uiso 1 calc R . . H27B H 0.5026 0.2061 -0.1927 0.052 Uiso 1 calc R . . C28 C 0.5534(4) 0.3390(3) -0.1314(3) 0.0578(12) Uani 1 d . . . H28A H 0.6125 0.3698 -0.0905 0.069 Uiso 1 calc R . . H28B H 0.4821 0.3429 -0.1177 0.069 Uiso 1 calc R . . H28C H 0.5593 0.3688 -0.1729 0.069 Uiso 1 calc R . . C29 C 0.7675(3) 0.2351(2) -0.12236(18) 0.0365(8) Uani 1 d . . . C30 C 0.7622(4) 0.2414(2) -0.04324(19) 0.0451(10) Uani 1 d . . . H30A H 0.6934 0.2624 -0.0349 0.054 Uiso 1 calc R . . H30B H 0.8245 0.2883 -0.0139 0.054 Uiso 1 calc R . . C31 C 0.8717(3) 0.2402(2) -0.14178(18) 0.0343(8) Uani 1 d . . . C32 C 0.9760(4) 0.2555(2) -0.08449(19) 0.0435(9) Uani 1 d . . . H32A H 1.0315 0.2248 -0.1050 0.052 Uiso 1 calc R . . H32B H 0.9596 0.2279 -0.0430 0.052 Uiso 1 calc R . . C33 C 1.0230(4) 0.3584(3) -0.0579(2) 0.0520(11) Uani 1 d . . . H33A H 1.0386 0.3859 -0.0990 0.062 Uiso 1 calc R . . H33B H 1.0910 0.3662 -0.0220 0.062 Uiso 1 calc R . . H33C H 0.9692 0.3884 -0.0358 0.062 Uiso 1 calc R . . C34 C 0.8795(3) 0.2392(2) -0.21473(17) 0.0291(7) Uani 1 d . . . C35 C 0.7841(3) 0.2354(2) -0.26692(16) 0.0266(6) Uani 1 d . . . C36 C 0.7954(3) 0.2460(2) -0.34309(17) 0.0282(7) Uani 1 d . . . H36A H 0.7288 0.2113 -0.3778 0.034 Uiso 1 calc R . . H36B H 0.8594 0.2201 -0.3555 0.034 Uiso 1 calc R . . C37 C 0.8107(3) 0.3476(2) -0.3501(2) 0.0386(8) Uani 1 d . . . H37A H 0.7457 0.3726 -0.3403 0.046 Uiso 1 calc R . . H37B H 0.8203 0.3526 -0.3993 0.046 Uiso 1 calc R . . H37C H 0.8757 0.3824 -0.3152 0.046 Uiso 1 calc R . . C38 C 0.9887(3) 0.2473(2) -0.23769(18) 0.0314(7) Uani 1 d . . . H38A H 1.0475 0.2744 -0.1948 0.038 Uiso 1 calc R . . H38B H 0.9908 0.2895 -0.2723 0.038 Uiso 1 calc R . . C39 C 1.0628(3) 0.1036(2) -0.21986(19) 0.0366(8) Uani 1 d . . . H39A H 1.1288 0.1432 -0.1878 0.044 Uiso 1 calc R . . H39B H 1.0099 0.0856 -0.1893 0.044 Uiso 1 calc R . . C40 C 1.0946(3) 0.0192(2) -0.25864(18) 0.0314(7) Uani 1 d . . . C41 C 1.0204(3) -0.0632(2) -0.27849(18) 0.0312(7) Uani 1 d . . . H41 H 0.9493 -0.0660 -0.2670 0.037 Uiso 1 calc R . . C42 C 1.0484(3) -0.1414(2) -0.31492(17) 0.0305(7) Uani 1 d . . . C43 C 1.1532(3) -0.1373(2) -0.3299(2) 0.0362(8) Uani 1 d . . . H43 H 1.1736 -0.1909 -0.3537 0.043 Uiso 1 calc R . . C44 C 1.2286(3) -0.0555(3) -0.3104(2) 0.0405(8) Uani 1 d . . . H44 H 1.3004 -0.0534 -0.3206 0.049 Uiso 1 calc R . . C45 C 1.1989(3) 0.0227(2) -0.2763(2) 0.0391(8) Uani 1 d . . . H45 H 1.2494 0.0791 -0.2647 0.047 Uiso 1 calc R . . C46 C 0.9664(3) -0.2299(2) -0.33816(19) 0.0360(8) Uani 1 d . . . H46A H 0.8917 -0.2162 -0.3515 0.043 Uiso 1 calc R . . H46B H 0.9834 -0.2668 -0.3815 0.043 Uiso 1 calc R . . C47 C 0.9067(3) -0.3822(2) -0.30192(18) 0.0295(7) Uani 1 d . . . H47A H 0.9019 -0.4037 -0.3544 0.035 Uiso 1 calc R . . H47B H 0.9474 -0.4220 -0.2756 0.035 Uiso 1 calc R . . C48 C 0.7925(2) -0.3893(2) -0.28560(17) 0.0271(6) Uani 1 d . . . C49 C 0.7018(3) -0.3891(2) -0.33981(17) 0.0296(7) Uani 1 d . . . C50 C 0.7156(3) -0.3851(2) -0.41631(18) 0.0343(7) Uani 1 d . . . H50A H 0.7897 -0.3505 -0.4150 0.041 Uiso 1 calc R . . H50B H 0.6609 -0.3514 -0.4381 0.041 Uiso 1 calc R . . C51 C 0.7015(4) -0.4799(3) -0.4642(2) 0.0456(9) Uani 1 d . . . H51A H 0.7626 -0.5098 -0.4476 0.055 Uiso 1 calc R . . H51B H 0.7008 -0.4734 -0.5145 0.055 Uiso 1 calc R . . H51C H 0.6320 -0.5173 -0.4611 0.055 Uiso 1 calc R . . C52 C 0.7803(3) -0.3885(2) -0.21325(17) 0.0271(6) Uani 1 d . . . C53 C 0.8793(3) -0.3863(2) -0.15473(18) 0.0322(7) Uani 1 d . . . H53A H 0.8726 -0.3463 -0.1095 0.039 Uiso 1 calc R . . H53B H 0.9466 -0.3592 -0.1698 0.039 Uiso 1 calc R . . C54 C 0.8907(3) -0.4811(3) -0.1397(2) 0.0439(9) Uani 1 d . . . H54A H 0.8231 -0.5093 -0.1266 0.053 Uiso 1 calc R . . H54B H 0.9528 -0.4755 -0.0996 0.053 Uiso 1 calc R . . H54C H 0.9035 -0.5194 -0.1831 0.053 Uiso 1 calc R . . S1 S 0.78879(6) 0.28994(5) 0.15649(4) 0.02608(18) Uani 1 d . . . O11 O 0.8245(2) 0.3086(2) 0.23527(13) 0.0514(7) Uani 1 d . . . O12 O 0.67420(19) 0.24352(18) 0.13588(16) 0.0473(7) Uani 1 d . . . O13 O 0.85877(19) 0.23103(18) 0.12476(14) 0.0394(6) Uani 1 d . . . O14 O 0.8013(3) 0.37688(19) 0.13120(18) 0.0547(8) Uani 1 d . . . S2 S 0.72695(6) -0.14332(5) -0.23674(4) 0.02722(19) Uani 1 d . . . O21 O 0.63855(19) -0.17889(16) -0.20088(13) 0.0337(5) Uani 1 d . . . O22 O 0.7438(2) -0.04171(15) -0.22224(13) 0.0337(5) Uani 1 d . . . O23 O 0.82899(19) -0.17276(16) -0.20731(13) 0.0348(5) Uani 1 d . . . O24 O 0.6957(2) -0.17703(17) -0.31572(12) 0.0355(5) Uani 1 d . . . S31 S 0.73380(10) 0.75569(9) 0.35720(9) 0.0276(5) Uani 0.592(4) d PD A 1 O311 O 0.8570(4) 0.7852(6) 0.3608(5) 0.0372(19) Uani 0.592(4) d PD A 1 O321 O 0.7201(5) 0.6658(3) 0.3825(3) 0.0470(14) Uani 0.592(4) d PDU A 1 O331 O 0.6783(5) 0.7514(4) 0.2803(2) 0.0387(14) Uani 0.592(4) d PD A 1 O341 O 0.6871(3) 0.8223(3) 0.4049(2) 0.0440(11) Uani 0.592(4) d PD A 1 S32 S 0.74960(19) 0.73773(15) 0.31119(15) 0.0377(8) Uani 0.408(4) d PD A 2 O312 O 0.8440(8) 0.8090(9) 0.3607(9) 0.058(5) Uani 0.408(4) d PD A 2 O322 O 0.7121(7) 0.6719(5) 0.3594(4) 0.0374(18) Uani 0.408(4) d PDU A 2 O332 O 0.6572(7) 0.7881(7) 0.2880(6) 0.063(3) Uani 0.408(4) d PD A 2 O342 O 0.7814(5) 0.6860(4) 0.2449(3) 0.0470(18) Uani 0.408(4) d PD A 2 OW1 O 0.80866(19) 0.03546(16) -0.33900(12) 0.0339(5) Uani 1 d . . . OW2 O 0.4617(2) -0.3070(2) -0.03930(16) 0.0517(7) Uani 1 d . . . OW3 O 0.4657(2) 0.98532(17) 0.23114(13) 0.0394(6) Uani 1 d . . . OW4 O 0.1062(3) 0.95133(19) 0.09628(14) 0.0521(7) Uani 1 d . . . OW5 O 0.5763(2) 0.17394(18) 0.24877(15) 0.0427(6) Uani 1 d . . . OW6 O 0.8956(2) 0.5410(2) 0.2333(2) 0.0650(10) Uani 1 d . . . OW7 O 0.0123(3) 0.1168(3) 0.08400(18) 0.0769(11) Uani 1 d . . . OW8 O 0.7682(4) 0.3704(3) 0.3673(2) 0.0811(12) Uani 1 d . . . OW9 O 0.8666(4) 0.5570(3) 0.3793(2) 0.0836(11) Uani 1 d . . . OW11 O 0.9314(8) 0.8245(7) 0.4979(4) 0.099(3) Uani 0.50 d P . . OW12 O 1.0169(7) 0.7787(11) 0.4784(5) 0.148(6) Uani 0.50 d P . . OW13 O 0.7480(4) 0.6490(3) 0.1650(3) 0.0332(10) Uani 0.50 d P B 1 OW14 O 0.7154(7) 0.6374(5) 0.1008(5) 0.082(2) Uani 0.50 d P C 2 OW15 O 0.2337(5) 0.1342(3) 0.4401(2) 0.0633(12) Uani 0.75 d P D 1 OW16 O 0.1407(15) 0.0865(13) 0.4637(8) 0.096(7) Uani 0.25 d P E 2 OW10 O 0.5115(4) 0.6167(4) 0.4150(3) 0.0416(12) Uani 0.50 d P . . OW17 O 0.5829(6) 0.7455(5) 0.4460(4) 0.0662(17) Uani 0.50 d P . . OW18 O 0.9661(10) 0.9700(16) 0.4703(10) 0.269(14) Uani 0.50 d P . . OW19 O 1.0544(17) 0.6617(11) 0.5121(11) 0.077(7) Uani 0.25 d P F 1 OW20 O 1.0354(12) 0.6170(16) 0.5169(11) 0.092(8) Uani 0.25 d P G 2 OW21 O 0.7812(6) 0.4718(5) 0.0275(4) 0.0676(18) Uani 0.50 d P . . OW22 O 0.6632(8) 0.4892(5) 0.0594(4) 0.091(3) Uani 0.50 d P H 1 OW23 O 0.5442(7) 0.4913(5) 0.0203(4) 0.079(2) Uani 0.50 d P . 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 N1 0.091(3) 0.0246(15) 0.0268(14) 0.0079(11) 0.0206(15) 0.0184(16) N2 0.0293(13) 0.0243(14) 0.0358(14) 0.0024(11) 0.0095(11) 0.0083(11) N3 0.0278(13) 0.0377(17) 0.0354(14) -0.0049(12) 0.0007(11) 0.0077(12) N4 0.0311(13) 0.0387(17) 0.0488(17) 0.0257(14) 0.0218(12) 0.0150(12) N5 0.0296(13) 0.0227(14) 0.0345(14) 0.0028(11) 0.0047(10) 0.0054(11) N6 0.0294(13) 0.0259(14) 0.0307(13) 0.0000(11) 0.0076(10) 0.0007(11) C1 0.093(3) 0.0252(19) 0.0310(17) 0.0068(14) 0.0151(19) 0.012(2) C2 0.082(3) 0.0258(18) 0.0285(16) 0.0030(14) 0.0156(17) 0.0104(19) C3 0.062(2) 0.0254(17) 0.0282(16) 0.0015(13) 0.0117(15) 0.0103(16) C4 0.060(2) 0.037(2) 0.0300(16) 0.0099(15) 0.0163(16) 0.0085(18) C5 0.068(3) 0.036(2) 0.0375(18) 0.0146(16) 0.0135(17) 0.0115(19) C6 0.0433(19) 0.0320(19) 0.0400(18) 0.0043(15) 0.0036(15) 0.0060(16) C7 0.055(2) 0.038(2) 0.0308(16) 0.0074(15) 0.0096(15) 0.0077(17) C8 0.0415(19) 0.038(2) 0.048(2) 0.0063(16) 0.0035(16) 0.0086(16) C9 0.0376(17) 0.0231(17) 0.0418(18) 0.0043(13) 0.0163(14) 0.0097(14) C10 0.0320(15) 0.0157(15) 0.0380(16) 0.0014(12) 0.0116(13) 0.0047(12) C11 0.0287(15) 0.0181(16) 0.0464(18) -0.0029(13) 0.0097(13) 0.0029(12) C12 0.0299(16) 0.0310(19) 0.053(2) -0.0034(16) 0.0152(15) 0.0066(14) C13 0.040(2) 0.040(2) 0.101(4) 0.008(2) 0.028(2) -0.0003(18) C14 0.0274(15) 0.0205(16) 0.0416(18) -0.0066(13) 0.0023(13) 0.0027(13) C15 0.0310(16) 0.0324(19) 0.0459(19) -0.0080(15) -0.0006(14) 0.0031(14) C16 0.051(2) 0.049(2) 0.0268(16) 0.0002(15) -0.0003(15) 0.0029(18) C17 0.0380(17) 0.047(2) 0.0231(14) 0.0100(14) 0.0064(12) -0.0016(15) C18 0.0335(17) 0.062(3) 0.0335(17) 0.0215(17) 0.0028(13) -0.0115(17) C19 0.0290(18) 0.076(3) 0.062(2) 0.041(2) -0.0102(16) -0.0089(19) C20 0.0305(17) 0.063(3) 0.071(3) 0.047(2) -0.0043(17) -0.0036(18) C21 0.0255(15) 0.050(2) 0.0330(16) 0.0225(15) 0.0067(12) 0.0014(14) C22 0.0275(15) 0.049(2) 0.0263(14) 0.0124(14) 0.0032(12) 0.0025(14) C23 0.0261(14) 0.042(2) 0.0333(16) 0.0186(14) 0.0096(12) 0.0057(14) C24 0.0396(17) 0.0330(18) 0.0416(18) 0.0201(15) 0.0222(14) 0.0163(15) C25 0.0425(17) 0.0239(16) 0.0325(15) 0.0133(13) 0.0175(13) 0.0163(14) C26 0.057(2) 0.0190(16) 0.0376(17) 0.0114(13) 0.0259(15) 0.0175(15) C27 0.063(2) 0.034(2) 0.049(2) 0.0174(16) 0.0378(19) 0.0206(18) C28 0.084(3) 0.042(2) 0.068(3) 0.019(2) 0.046(3) 0.034(2) C29 0.069(2) 0.0208(16) 0.0281(15) 0.0088(12) 0.0190(16) 0.0188(16) C30 0.091(3) 0.0224(17) 0.0303(17) 0.0085(13) 0.0242(18) 0.0189(19) C31 0.056(2) 0.0184(16) 0.0302(16) 0.0044(12) 0.0083(15) 0.0132(15) C32 0.070(3) 0.0298(19) 0.0294(16) 0.0030(14) -0.0002(16) 0.0193(18) C33 0.076(3) 0.034(2) 0.0386(19) -0.0020(16) -0.0076(19) 0.019(2) C34 0.0417(17) 0.0187(15) 0.0288(15) 0.0039(12) 0.0082(13) 0.0108(13) C35 0.0394(16) 0.0190(15) 0.0275(14) 0.0078(12) 0.0147(12) 0.0116(13) C36 0.0313(15) 0.0284(17) 0.0300(15) 0.0117(12) 0.0118(12) 0.0085(13) C37 0.051(2) 0.0345(19) 0.0395(18) 0.0182(15) 0.0203(16) 0.0130(16) C38 0.0363(16) 0.0206(16) 0.0352(16) 0.0019(12) 0.0045(13) 0.0053(13) C39 0.0448(19) 0.0265(17) 0.0361(17) 0.0029(13) -0.0002(14) 0.0116(15) C40 0.0337(16) 0.0243(16) 0.0352(16) 0.0060(13) 0.0007(13) 0.0085(13) C41 0.0273(15) 0.0290(17) 0.0381(17) 0.0085(14) 0.0043(12) 0.0074(13) C42 0.0305(15) 0.0253(17) 0.0338(16) 0.0057(13) 0.0012(12) 0.0051(13) C43 0.0375(17) 0.0272(18) 0.0453(19) 0.0054(14) 0.0089(15) 0.0112(15) C44 0.0293(16) 0.035(2) 0.060(2) 0.0114(17) 0.0098(15) 0.0105(15) C45 0.0310(16) 0.0262(18) 0.055(2) 0.0065(15) -0.0011(15) 0.0020(14) C46 0.0376(17) 0.0280(18) 0.0373(17) 0.0044(14) -0.0001(14) 0.0007(14) C47 0.0292(15) 0.0230(16) 0.0352(16) -0.0004(12) 0.0098(12) 0.0042(13) C48 0.0287(14) 0.0175(15) 0.0344(15) -0.0003(12) 0.0085(12) 0.0055(12) C49 0.0323(15) 0.0172(15) 0.0353(16) -0.0040(12) 0.0058(13) 0.0028(13) C50 0.0336(16) 0.0297(18) 0.0336(16) 0.0002(13) 0.0002(13) 0.0012(14) C51 0.060(2) 0.038(2) 0.0327(17) -0.0055(15) 0.0047(16) 0.0059(18) C52 0.0302(15) 0.0153(14) 0.0350(16) 0.0014(12) 0.0062(12) 0.0057(12) C53 0.0351(16) 0.0304(18) 0.0325(16) 0.0048(13) 0.0079(13) 0.0107(14) C54 0.055(2) 0.038(2) 0.046(2) 0.0104(16) 0.0129(17) 0.0241(18) S1 0.0243(3) 0.0236(4) 0.0281(4) 0.0026(3) 0.0010(3) 0.0043(3) O11 0.0531(16) 0.075(2) 0.0270(12) 0.0035(12) 0.0021(11) 0.0273(15) O12 0.0251(12) 0.0375(15) 0.0704(18) 0.0006(13) -0.0002(11) -0.0007(11) O13 0.0321(12) 0.0430(15) 0.0434(14) 0.0016(11) 0.0080(10) 0.0150(11) O14 0.0579(17) 0.0365(15) 0.075(2) 0.0242(14) 0.0145(15) 0.0078(13) S2 0.0293(4) 0.0227(4) 0.0293(4) 0.0019(3) 0.0058(3) 0.0069(3) O21 0.0352(12) 0.0309(13) 0.0388(12) 0.0082(10) 0.0134(10) 0.0093(10) O22 0.0435(13) 0.0214(12) 0.0378(12) 0.0035(9) 0.0105(10) 0.0102(10) O23 0.0322(12) 0.0292(13) 0.0405(13) 0.0011(10) 0.0025(10) 0.0092(10) O24 0.0398(13) 0.0351(13) 0.0296(11) 0.0011(10) 0.0060(9) 0.0073(11) S31 0.0258(6) 0.0235(7) 0.0349(10) 0.0062(6) 0.0097(5) 0.0044(5) O311 0.022(3) 0.039(5) 0.053(4) 0.005(3) 0.016(2) 0.007(3) O321 0.049(2) 0.044(2) 0.049(2) 0.0124(17) 0.0083(17) 0.0114(15) O331 0.029(3) 0.052(4) 0.033(2) 0.007(2) -0.002(2) 0.011(2) O341 0.040(2) 0.045(3) 0.046(2) -0.004(2) 0.0063(19) 0.021(2) S32 0.0377(12) 0.0287(12) 0.0471(18) 0.0016(10) 0.0211(11) -0.0005(9) O312 0.030(4) 0.033(7) 0.107(10) -0.015(6) 0.024(5) 0.016(4) O322 0.040(2) 0.034(2) 0.040(2) 0.0091(18) 0.0097(18) 0.0080(17) O332 0.043(5) 0.059(8) 0.088(7) -0.005(5) 0.040(4) 0.010(4) O342 0.043(4) 0.043(4) 0.053(4) -0.006(3) 0.025(3) 0.003(3) OW1 0.0344(12) 0.0274(12) 0.0376(12) 0.0059(10) 0.0020(9) 0.0044(10) OW2 0.0387(14) 0.064(2) 0.0535(17) 0.0067(14) 0.0137(12) 0.0123(13) OW3 0.0579(16) 0.0327(13) 0.0399(13) 0.0169(11) 0.0244(11) 0.0195(12) OW4 0.081(2) 0.0385(15) 0.0363(14) 0.0002(11) 0.0048(13) 0.0236(15) OW5 0.0416(14) 0.0411(15) 0.0512(15) 0.0141(12) 0.0162(11) 0.0118(12) OW6 0.0418(15) 0.0333(16) 0.121(3) 0.0050(17) 0.0331(17) 0.0028(13) OW7 0.077(2) 0.097(3) 0.0515(19) -0.0099(18) -0.0100(16) 0.049(2) OW8 0.127(3) 0.070(2) 0.081(2) 0.031(2) 0.071(2) 0.051(2) OW9 0.097(3) 0.060(2) 0.103(3) 0.014(2) 0.032(2) 0.031(2) OW11 0.099(7) 0.135(8) 0.044(4) -0.004(4) 0.018(4) -0.011(6) OW12 0.049(5) 0.299(17) 0.082(6) 0.073(8) -0.027(4) -0.009(7) OW13 0.031(2) 0.033(3) 0.034(2) 0.0014(19) 0.0109(19) 0.0003(19) OW14 0.072(5) 0.063(5) 0.119(7) 0.021(5) 0.036(5) 0.015(4) OW15 0.098(4) 0.050(3) 0.040(2) 0.0079(18) -0.003(2) 0.027(2) OW16 0.091(11) 0.107(13) 0.064(9) -0.049(9) -0.047(9) 0.080(11) OW10 0.041(3) 0.042(3) 0.046(3) 0.010(2) 0.024(2) 0.003(2) OW17 0.062(4) 0.070(5) 0.069(4) 0.012(3) 0.021(3) 0.015(3) OW18 0.076(7) 0.38(3) 0.226(17) -0.214(19) -0.043(9) 0.047(11) OW19 0.084(12) 0.042(9) 0.083(11) -0.047(8) 0.052(9) -0.037(8) OW20 0.028(7) 0.115(18) 0.089(13) -0.072(14) -0.001(7) -0.007(10) OW21 0.068(4) 0.052(4) 0.084(5) 0.015(3) 0.026(4) 0.000(3) OW22 0.117(7) 0.061(4) 0.069(5) 0.005(4) -0.044(5) 0.014(4) OW23 0.112(7) 0.052(4) 0.074(5) -0.001(3) 0.017(4) 0.038(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 N1 C1 1.485(6) . ? N1 C30 1.518(4) . ? N1 H1A 0.9200 . ? N1 H1B 0.9200 . ? N2 C9 1.515(4) . ? N2 C8 1.517(4) . ? N2 H2A 0.9200 . ? N2 H2B 0.9200 . ? N3 C16 1.478(4) . ? N3 C15 1.512(5) . ? N3 H3A 0.9200 . ? N3 H3B 0.9200 . ? N4 C23 1.493(5) . ? N4 C24 1.517(5) . ? N4 H4A 0.9200 . ? N4 H4B 0.9200 . ? N5 C39 1.503(4) . ? N5 C38 1.512(4) . ? N5 H5A 0.9200 . ? N5 H5B 0.9200 . ? N6 C46 1.485(4) . ? N6 C47 1.521(4) . ? N6 H6A 0.9200 . ? N6 H6B 0.9200 . ? C1 C2 1.518(5) . ? C1 H1C 0.9900 . ? C1 H1D 0.9900 . ? C2 C3 1.391(5) . ? C2 C7 1.400(6) . ? C3 C4 1.393(5) . ? C3 H3 0.9500 . ? C4 C5 1.382(6) . ? C4 H4 0.9500 . ? C5 C6 1.398(5) . ? C5 H5 0.9500 . ? C6 C7 1.390(5) . ? C6 C8 1.506(6) . ? C7 H7 0.9500 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.513(5) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.401(5) . ? C10 C52 1.404(4) . ? C11 C14 1.399(5) . ? C11 C12 1.526(5) . ? C12 C13 1.520(5) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C49 1.410(5) . ? C14 C15 1.517(5) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.507(6) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.381(5) . ? C17 C22 1.406(5) . ? C18 C19 1.373(6) . ? C18 H18 0.9500 . ? C19 C20 1.394(6) . ? C19 H19 0.9500 . ? C20 C21 1.390(5) . ? C20 H20 0.9500 . ? C21 C22 1.382(5) . ? C21 C23 1.516(5) . ? C22 H22 0.9500 . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.514(5) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 C35 1.405(4) . ? C25 C26 1.410(4) . ? C26 C29 1.398(5) . ? C26 C27 1.517(5) . ? C27 C28 1.537(6) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 C31 1.412(5) . ? C29 C30 1.511(4) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 C34 1.410(4) . ? C31 C32 1.521(5) . ? C32 C33 1.538(5) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C34 C35 1.412(4) . ? C34 C38 1.502(5) . ? C35 C36 1.516(4) . ? C36 C37 1.542(5) . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C38 H38A 0.9900 . ? C38 H38B 0.9900 . ? C39 C40 1.502(5) . ? C39 H39A 0.9900 . ? C39 H39B 0.9900 . ? C40 C41 1.389(4) . ? C40 C45 1.400(5) . ? C41 C42 1.388(5) . ? C41 H41 0.9500 . ? C42 C43 1.386(5) . ? C42 C46 1.507(4) . ? C43 C44 1.389(5) . ? C43 H43 0.9500 . ? C44 C45 1.381(6) . ? C44 H44 0.9500 . ? C45 H45 0.9500 . ? C46 H46A 0.9900 . ? C46 H46B 0.9900 . ? C47 C48 1.508(4) . ? C47 H47A 0.9900 . ? C47 H47B 0.9900 . ? C48 C49 1.406(4) . ? C48 C52 1.413(4) . ? C49 C50 1.509(5) . ? C50 C51 1.529(5) . ? C50 H50A 0.9900 . ? C50 H50B 0.9900 . ? C51 H51A 0.9800 . ? C51 H51B 0.9800 . ? C51 H51C 0.9800 . ? C52 C53 1.518(4) . ? C53 C54 1.522(5) . ? C53 H53A 0.9900 . ? C53 H53B 0.9900 . ? C54 H54A 0.9800 . ? C54 H54B 0.9800 . ? C54 H54C 0.9800 . ? S1 O12 1.460(2) . ? S1 O14 1.463(3) . ? S1 O11 1.463(3) . ? S1 O13 1.468(3) . ? S2 O23 1.471(2) . ? S2 O24 1.475(2) . ? S2 O21 1.477(2) . ? S2 O22 1.484(2) . ? S31 O341 1.493(4) . ? S31 O331 1.504(4) . ? S31 O321 1.504(4) . ? S31 O311 1.530(4) . ? S32 O342 1.518(4) . ? S32 O332 1.522(5) . ? S32 O322 1.534(4) . ? S32 O312 1.535(5) . ? OW11 OW12 1.426(16) . ? OW18 OW18 1.39(2) 2_776 ? OW21 OW22 1.731(12) . ? OW23 OW23 1.329(15) 2_665 ? 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 C1 N1 C30 114.2(3) . . ? C1 N1 H1A 108.7 . . ? C30 N1 H1A 108.7 . . ? C1 N1 H1B 108.7 . . ? C30 N1 H1B 108.7 . . ? H1A N1 H1B 107.6 . . ? C9 N2 C8 116.2(3) . . ? C9 N2 H2A 108.2 . . ? C8 N2 H2A 108.2 . . ? C9 N2 H2B 108.2 . . ? C8 N2 H2B 108.2 . . ? H2A N2 H2B 107.4 . . ? C16 N3 C15 111.4(3) . . ? C16 N3 H3A 109.3 . . ? C15 N3 H3A 109.3 . . ? C16 N3 H3B 109.3 . . ? C15 N3 H3B 109.3 . . ? H3A N3 H3B 108.0 . . ? C23 N4 C24 115.1(2) . . ? C23 N4 H4A 108.5 . . ? C24 N4 H4A 108.5 . . ? C23 N4 H4B 108.5 . . ? C24 N4 H4B 108.5 . . ? H4A N4 H4B 107.5 . . ? C39 N5 C38 114.0(3) . . ? C39 N5 H5A 108.8 . . ? C38 N5 H5A 108.8 . . ? C39 N5 H5B 108.8 . . ? C38 N5 H5B 108.8 . . ? H5A N5 H5B 107.7 . . ? C46 N6 C47 115.5(2) . . ? C46 N6 H6A 108.4 . . ? C47 N6 H6A 108.4 . . ? C46 N6 H6B 108.4 . . ? C47 N6 H6B 108.4 . . ? H6A N6 H6B 107.5 . . ? N1 C1 C2 110.2(4) . . ? N1 C1 H1C 109.6 . . ? C2 C1 H1C 109.6 . . ? N1 C1 H1D 109.6 . . ? C2 C1 H1D 109.6 . . ? H1C C1 H1D 108.1 . . ? C3 C2 C7 119.7(3) . . ? C3 C2 C1 118.7(4) . . ? C7 C2 C1 121.5(3) . . ? C2 C3 C4 119.4(4) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C5 C4 C3 120.6(3) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 120.8(3) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C7 C6 C5 118.5(4) . . ? C7 C6 C8 121.1(4) . . ? C5 C6 C8 120.4(3) . . ? C6 C7 C2 121.0(3) . . ? C6 C7 H7 119.5 . . ? C2 C7 H7 119.5 . . ? C6 C8 N2 109.6(3) . . ? C6 C8 H8A 109.8 . . ? N2 C8 H8A 109.8 . . ? C6 C8 H8B 109.8 . . ? N2 C8 H8B 109.8 . . ? H8A C8 H8B 108.2 . . ? C10 C9 N2 110.5(3) . . ? C10 C9 H9A 109.6 . . ? N2 C9 H9A 109.6 . . ? C10 C9 H9B 109.6 . . ? N2 C9 H9B 109.6 . . ? H9A C9 H9B 108.1 . . ? C11 C10 C52 120.3(3) . . ? C11 C10 C9 119.4(3) . . ? C52 C10 C9 120.0(3) . . ? C14 C11 C10 119.7(3) . . ? C14 C11 C12 120.6(3) . . ? C10 C11 C12 119.7(3) . . ? C13 C12 C11 113.0(3) . . ? C13 C12 H12A 109.0 . . ? C11 C12 H12A 109.0 . . ? C13 C12 H12B 109.0 . . ? C11 C12 H12B 109.0 . . ? H12A C12 H12B 107.8 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 C14 C49 121.3(3) . . ? C11 C14 C15 118.9(3) . . ? C49 C14 C15 119.5(3) . . ? N3 C15 C14 110.8(3) . . ? N3 C15 H15A 109.5 . . ? C14 C15 H15A 109.5 . . ? N3 C15 H15B 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 108.1 . . ? N3 C16 C17 114.4(3) . . ? N3 C16 H16A 108.6 . . ? C17 C16 H16A 108.6 . . ? N3 C16 H16B 108.6 . . ? C17 C16 H16B 108.6 . . ? H16A C16 H16B 107.6 . . ? C18 C17 C22 119.3(4) . . ? C18 C17 C16 117.1(3) . . ? C22 C17 C16 123.4(3) . . ? C19 C18 C17 120.9(3) . . ? C19 C18 H18 119.5 . . ? C17 C18 H18 119.5 . . ? C18 C19 C20 119.6(3) . . ? C18 C19 H19 120.2 . . ? C20 C19 H19 120.2 . . ? C21 C20 C19 120.6(4) . . ? C21 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? C22 C21 C20 119.3(3) . . ? C22 C21 C23 121.7(3) . . ? C20 C21 C23 119.0(3) . . ? C21 C22 C17 120.3(3) . . ? C21 C22 H22 119.9 . . ? C17 C22 H22 119.9 . . ? N4 C23 C21 111.0(3) . . ? N4 C23 H23A 109.4 . . ? C21 C23 H23A 109.4 . . ? N4 C23 H23B 109.4 . . ? C21 C23 H23B 109.4 . . ? H23A C23 H23B 108.0 . . ? C25 C24 N4 113.8(3) . . ? C25 C24 H24A 108.8 . . ? N4 C24 H24A 108.8 . . ? C25 C24 H24B 108.8 . . ? N4 C24 H24B 108.8 . . ? H24A C24 H24B 107.7 . . ? C35 C25 C26 119.9(3) . . ? C35 C25 C24 121.1(3) . . ? C26 C25 C24 118.8(3) . . ? C29 C26 C25 119.7(3) . . ? C29 C26 C27 121.2(3) . . ? C25 C26 C27 118.7(3) . . ? C26 C27 C28 110.0(3) . . ? C26 C27 H27A 109.7 . . ? C28 C27 H27A 109.7 . . ? C26 C27 H27B 109.7 . . ? C28 C27 H27B 109.7 . . ? H27A C27 H27B 108.2 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C26 C29 C31 121.0(3) . . ? C26 C29 C30 120.8(4) . . ? C31 C29 C30 118.1(3) . . ? C29 C30 N1 113.9(3) . . ? C29 C30 H30A 108.8 . . ? N1 C30 H30A 108.8 . . ? C29 C30 H30B 108.8 . . ? N1 C30 H30B 108.8 . . ? H30A C30 H30B 107.7 . . ? C34 C31 C29 119.2(3) . . ? C34 C31 C32 119.6(3) . . ? C29 C31 C32 121.0(3) . . ? C31 C32 C33 111.1(3) . . ? C31 C32 H32A 109.4 . . ? C33 C32 H32A 109.4 . . ? C31 C32 H32B 109.4 . . ? C33 C32 H32B 109.4 . . ? H32A C32 H32B 108.0 . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C31 C34 C35 120.0(3) . . ? C31 C34 C38 121.1(3) . . ? C35 C34 C38 118.8(3) . . ? C25 C35 C34 120.2(3) . . ? C25 C35 C36 120.2(3) . . ? C34 C35 C36 119.3(3) . . ? C35 C36 C37 111.3(3) . . ? C35 C36 H36A 109.4 . . ? C37 C36 H36A 109.4 . . ? C35 C36 H36B 109.4 . . ? C37 C36 H36B 109.4 . . ? H36A C36 H36B 108.0 . . ? C36 C37 H37A 109.5 . . ? C36 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C36 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C34 C38 N5 113.0(3) . . ? C34 C38 H38A 109.0 . . ? N5 C38 H38A 109.0 . . ? C34 C38 H38B 109.0 . . ? N5 C38 H38B 109.0 . . ? H38A C38 H38B 107.8 . . ? C40 C39 N5 111.0(3) . . ? C40 C39 H39A 109.4 . . ? N5 C39 H39A 109.4 . . ? C40 C39 H39B 109.4 . . ? N5 C39 H39B 109.4 . . ? H39A C39 H39B 108.0 . . ? C41 C40 C45 118.9(3) . . ? C41 C40 C39 120.5(3) . . ? C45 C40 C39 120.6(3) . . ? C42 C41 C40 121.0(3) . . ? C42 C41 H41 119.5 . . ? C40 C41 H41 119.5 . . ? C43 C42 C41 119.2(3) . . ? C43 C42 C46 120.1(3) . . ? C41 C42 C46 120.7(3) . . ? C42 C43 C44 120.6(3) . . ? C42 C43 H43 119.7 . . ? C44 C43 H43 119.7 . . ? C45 C44 C43 119.8(3) . . ? C45 C44 H44 120.1 . . ? C43 C44 H44 120.1 . . ? C44 C45 C40 120.4(3) . . ? C44 C45 H45 119.8 . . ? C40 C45 H45 119.8 . . ? N6 C46 C42 111.3(3) . . ? N6 C46 H46A 109.4 . . ? C42 C46 H46A 109.4 . . ? N6 C46 H46B 109.4 . . ? C42 C46 H46B 109.4 . . ? H46A C46 H46B 108.0 . . ? C48 C47 N6 110.8(3) . . ? C48 C47 H47A 109.5 . . ? N6 C47 H47A 109.5 . . ? C48 C47 H47B 109.5 . . ? N6 C47 H47B 109.5 . . ? H47A C47 H47B 108.1 . . ? C49 C48 C52 120.8(3) . . ? C49 C48 C47 120.7(3) . . ? C52 C48 C47 118.3(3) . . ? C48 C49 C14 118.4(3) . . ? C48 C49 C50 120.9(3) . . ? C14 C49 C50 120.7(3) . . ? C49 C50 C51 113.1(3) . . ? C49 C50 H50A 109.0 . . ? C51 C50 H50A 109.0 . . ? C49 C50 H50B 109.0 . . ? C51 C50 H50B 109.0 . . ? H50A C50 H50B 107.8 . . ? C50 C51 H51A 109.5 . . ? C50 C51 H51B 109.5 . . ? H51A C51 H51B 109.5 . . ? C50 C51 H51C 109.5 . . ? H51A C51 H51C 109.5 . . ? H51B C51 H51C 109.5 . . ? C10 C52 C48 119.5(3) . . ? C10 C52 C53 120.1(3) . . ? C48 C52 C53 120.4(3) . . ? C52 C53 C54 112.7(3) . . ? C52 C53 H53A 109.1 . . ? C54 C53 H53A 109.1 . . ? C52 C53 H53B 109.1 . . ? C54 C53 H53B 109.1 . . ? H53A C53 H53B 107.8 . . ? C53 C54 H54A 109.5 . . ? C53 C54 H54B 109.5 . . ? H54A C54 H54B 109.5 . . ? C53 C54 H54C 109.5 . . ? H54A C54 H54C 109.5 . . ? H54B C54 H54C 109.5 . . ? O12 S1 O14 109.91(17) . . ? O12 S1 O11 110.38(18) . . ? O14 S1 O11 108.81(19) . . ? O12 S1 O13 109.62(16) . . ? O14 S1 O13 109.93(17) . . ? O11 S1 O13 108.16(16) . . ? O23 S2 O24 110.50(15) . . ? O23 S2 O21 109.14(14) . . ? O24 S2 O21 110.17(14) . . ? O23 S2 O22 109.54(14) . . ? O24 S2 O22 108.49(14) . . ? O21 S2 O22 108.98(14) . . ? O341 S31 O331 107.6(3) . . ? O341 S31 O321 108.4(3) . . ? O331 S31 O321 114.9(3) . . ? O341 S31 O311 113.1(4) . . ? O331 S31 O311 106.5(4) . . ? O321 S31 O311 106.4(5) . . ? O342 S32 O332 109.9(5) . . ? O342 S32 O322 110.8(4) . . ? O332 S32 O322 109.3(6) . . ? O342 S32 O312 114.1(7) . . ? O332 S32 O312 107.4(8) . . ? O322 S32 O312 105.1(8) . . ? _diffrn_measured_fraction_theta_max 0.868 _diffrn_reflns_theta_full 29.12 _diffrn_measured_fraction_theta_full 0.868 _refine_diff_density_max 1.342 _refine_diff_density_min -0.585 _refine_diff_density_rms 0.096