# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Bradley Smith' _publ_contact_author_email SMITH.115@ND.EDU loop_ _publ_author_name B.Smith J.M.Baumes J.Eberhard J.J.Gassensmith data_jjg_sq _database_code_depnum_ccdc_archive 'CCDC 717858' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C46 H36 N6 O8, O H2, 4(C H Cl3)' _chemical_formula_sum 'C50 H42 Cl12 N6 O9' _chemical_formula_weight 1296.30 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 17.4237(13) _cell_length_b 18.9917(14) _cell_length_c 17.0898(12) _cell_angle_alpha 90.00 _cell_angle_beta 102.159(3) _cell_angle_gamma 90.00 _cell_volume 5528.2(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 78882 _cell_measurement_theta_min 1.20 _cell_measurement_theta_max 25.030 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.557 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2640 _exptl_absorpt_coefficient_mu 0.662 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7749 _exptl_absorpt_correction_T_max 0.9677 _exptl_absorpt_process_details ; Blessing, R. H. (1995) Acta Cryst. A51, 33-38. Sheldrick, G. M. (2004) SADABS University of G\"ottingen, Germany. ; _exptl_special_details ; Modeling of highly disordered solvent proved unsuccessful. In the asymmetric unit four chloroforms could be distinguished but none could be adequately refined. It is apparent that there are two regions of solvent. One of which forms large sheets of solvents as planes through the lattice and anothe which forms between two cofacial macrocycles. Platon SQUEEZE was executed to remove all halogenated solvent. Remaining is a single molecule of water whose protons were found in the difference map. The crystal size was very small and diffraction data at high angles are very weak or absent resulting in a higher Rint for redundant data. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_source_type 'Siemens KFFMO2K-90' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker d8-APEX II CCD diffractometer' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.33 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 78882 _diffrn_reflns_av_R_equivalents 0.1208 _diffrn_reflns_av_sigmaI/netI 0.0524 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.20 _diffrn_reflns_theta_max 25.03 _reflns_number_total 9771 _reflns_number_gt 7318 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_cell_refinement 'APEX2/SAINT (Bruker, 2004)' _computing_data_reduction 'SAINT/XPREP (Bruker, 2004; Sheldrick, 2003)' _computing_structure_solution 'XS (Sheldrick, 2001)' _computing_structure_refinement 'XL (Sheldrick, 2001)' _computing_molecular_graphics 'XP (Sheldrick, 1998)' _computing_publication_material 'enCIFer (CCDC, 2004)' _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^)+(0.1179P)^2^+0.7828P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9771 _refine_ls_number_parameters 574 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0797 _refine_ls_R_factor_gt 0.0649 _refine_ls_wR_factor_ref 0.1908 _refine_ls_wR_factor_gt 0.1833 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.01038(14) 0.27331(12) -0.10728(14) 0.0217(5) Uani 1 1 d . . . C2 C 1.02287(15) 0.29944(13) -0.17882(15) 0.0273(6) Uani 1 1 d . . . H2A H 0.9866 0.2905 -0.2276 0.033 Uiso 1 1 calc R . . C3 C 1.08937(17) 0.33882(15) -0.17750(16) 0.0355(7) Uani 1 1 d . . . H3A H 1.0994 0.3582 -0.2256 0.043 Uiso 1 1 calc R . . C4 C 1.14127(16) 0.34995(14) -0.10572(16) 0.0329(6) Uani 1 1 d . . . H4A H 1.1882 0.3760 -0.1037 0.039 Uiso 1 1 calc R . . C5 C 1.12375(14) 0.32258(13) -0.03690(15) 0.0241(5) Uani 1 1 d . . . C6 C 1.17901(14) 0.33358(14) 0.04223(15) 0.0270(6) Uani 1 1 d . . . C7 C 1.19850(14) 0.31115(13) 0.18660(15) 0.0264(6) Uani 1 1 d . . . H7A H 1.2509 0.3308 0.1856 0.032 Uiso 1 1 calc R . . H7B H 1.2061 0.2619 0.2057 0.032 Uiso 1 1 calc R . . C8 C 1.16321(13) 0.35284(12) 0.24535(14) 0.0209(5) Uani 1 1 d . . . C9 C 1.20163(13) 0.33996(12) 0.33271(14) 0.0222(5) Uani 1 1 d . . . C10 C 1.26913(15) 0.30181(13) 0.36218(16) 0.0280(6) Uani 1 1 d . . . H10A H 1.2978 0.2807 0.3268 0.034 Uiso 1 1 calc R . . C11 C 1.29426(15) 0.29491(14) 0.44509(17) 0.0326(6) Uani 1 1 d . . . H11A H 1.3409 0.2693 0.4663 0.039 Uiso 1 1 calc R . . C12 C 1.25248(15) 0.32460(14) 0.49603(16) 0.0299(6) Uani 1 1 d . . . H12A H 1.2705 0.3195 0.5522 0.036 Uiso 1 1 calc R . . C13 C 1.18431(14) 0.36198(13) 0.46673(15) 0.0256(6) Uani 1 1 d . . . H13A H 1.1548 0.3814 0.5024 0.031 Uiso 1 1 calc R . . C14 C 1.15938(14) 0.37083(12) 0.38445(14) 0.0219(5) Uani 1 1 d . . . C15 C 1.08881(13) 0.40986(12) 0.34046(14) 0.0202(5) Uani 1 1 d . . . C16 C 1.11388(13) 0.46301(12) 0.28566(13) 0.0198(5) Uani 1 1 d . . . C17 C 1.10061(14) 0.53444(13) 0.28264(14) 0.0237(5) Uani 1 1 d . . . H17A H 1.0728 0.5561 0.3184 0.028 Uiso 1 1 calc R . . C18 C 1.12859(14) 0.57442(13) 0.22640(14) 0.0248(5) Uani 1 1 d . . . H18A H 1.1208 0.6240 0.2246 0.030 Uiso 1 1 calc R . . C19 C 1.16744(15) 0.54293(14) 0.17328(15) 0.0275(6) Uani 1 1 d . . . H19A H 1.1850 0.5709 0.1344 0.033 Uiso 1 1 calc R . . C20 C 1.18121(14) 0.47121(13) 0.17577(14) 0.0237(5) Uani 1 1 d . . . H20A H 1.2085 0.4497 0.1395 0.028 Uiso 1 1 calc R . . C21 C 1.15423(13) 0.43120(12) 0.23255(13) 0.0196(5) Uani 1 1 d . . . C22 C 1.03581(14) 0.43494(13) 0.39548(14) 0.0229(5) Uani 1 1 d . . . H22A H 1.0348 0.3986 0.4368 0.027 Uiso 1 1 calc R . . H22B H 1.0582 0.4784 0.4231 0.027 Uiso 1 1 calc R . . C23 C 0.91841(15) 0.50784(13) 0.36248(14) 0.0234(5) Uani 1 1 d . . . C24 C 0.83260(14) 0.50787(13) 0.32280(14) 0.0226(5) Uani 1 1 d . . . C25 C 0.78944(15) 0.57061(13) 0.31879(15) 0.0279(6) Uani 1 1 d . . . H25A H 0.8134 0.6135 0.3397 0.034 Uiso 1 1 calc R . . C26 C 0.71037(16) 0.56730(15) 0.28299(17) 0.0364(7) Uani 1 1 d . . . H26A H 0.6790 0.6086 0.2785 0.044 Uiso 1 1 calc R . . C27 C 0.67756(16) 0.50470(15) 0.25414(15) 0.0313(6) Uani 1 1 d . . . H27A H 0.6233 0.5018 0.2302 0.038 Uiso 1 1 calc R . . C28 C 0.72533(14) 0.44487(13) 0.26048(13) 0.0233(5) Uani 1 1 d . . . C29 C 0.68996(14) 0.37499(14) 0.22993(13) 0.0228(5) Uani 1 1 d . . . C30 C 0.71853(14) 0.25231(12) 0.20573(13) 0.0199(5) Uani 1 1 d . . . H30A H 0.6605 0.2500 0.1919 0.024 Uiso 1 1 calc R . . H30B H 0.7368 0.2206 0.2519 0.024 Uiso 1 1 calc R . . C31 C 0.75054(13) 0.22572(12) 0.13488(13) 0.0176(5) Uani 1 1 d . . . C32 C 0.73393(13) 0.14881(12) 0.11593(13) 0.0199(5) Uani 1 1 d . . . C33 C 0.68688(14) 0.10405(13) 0.14903(15) 0.0251(5) Uani 1 1 d . . . H33A H 0.6618 0.1204 0.1899 0.030 Uiso 1 1 calc R . . C34 C 0.67659(15) 0.03559(14) 0.12242(17) 0.0331(6) Uani 1 1 d . . . H34A H 0.6436 0.0050 0.1445 0.040 Uiso 1 1 calc R . . C35 C 0.71373(15) 0.01094(13) 0.06400(17) 0.0319(6) Uani 1 1 d . . . H35A H 0.7058 -0.0363 0.0459 0.038 Uiso 1 1 calc R . . C36 C 0.76239(14) 0.05473(12) 0.03177(15) 0.0253(5) Uani 1 1 d . . . H36A H 0.7891 0.0375 -0.0074 0.030 Uiso 1 1 calc R . . C37 C 0.77177(13) 0.12436(13) 0.05748(14) 0.0212(5) Uani 1 1 d . . . C38 C 0.82274(13) 0.18010(12) 0.03147(13) 0.0186(5) Uani 1 1 d . . . C39 C 0.76993(13) 0.24209(12) 0.00072(13) 0.0170(5) Uani 1 1 d . . . C40 C 0.75694(13) 0.27196(12) -0.07479(13) 0.0196(5) Uani 1 1 d . . . H40A H 0.7859 0.2567 -0.1130 0.023 Uiso 1 1 calc R . . C41 C 0.70155(14) 0.32407(13) -0.09353(14) 0.0242(5) Uani 1 1 d . . . H41A H 0.6926 0.3452 -0.1450 0.029 Uiso 1 1 calc R . . C42 C 0.65886(14) 0.34618(13) -0.03901(14) 0.0250(5) Uani 1 1 d . . . H42A H 0.6195 0.3812 -0.0538 0.030 Uiso 1 1 calc R . . C43 C 0.67270(14) 0.31788(12) 0.03717(14) 0.0211(5) Uani 1 1 d . . . H43A H 0.6441 0.3340 0.0753 0.025 Uiso 1 1 calc R . . C44 C 0.72848(13) 0.26597(12) 0.05706(13) 0.0175(5) Uani 1 1 d . . . C45 C 0.87632(13) 0.15343(12) -0.02130(14) 0.0204(5) Uani 1 1 d . . . H45A H 0.9037 0.1107 0.0034 0.024 Uiso 1 1 calc R . . H45B H 0.8439 0.1398 -0.0739 0.024 Uiso 1 1 calc R . . C46 C 0.94022(13) 0.22675(12) -0.10646(13) 0.0200(5) Uani 1 1 d . . . N1 N 0.93430(12) 0.20437(11) -0.03391(12) 0.0218(4) Uani 1 1 d . . . N2 N 1.05919(11) 0.28419(11) -0.03696(11) 0.0218(4) Uani 1 1 d . . . N3 N 1.15198(12) 0.31086(11) 0.10613(12) 0.0261(5) Uani 1 1 d . . . N4 N 0.95623(12) 0.44887(11) 0.35288(12) 0.0222(4) Uani 1 1 d . . . N5 N 0.80167(11) 0.44703(11) 0.29393(11) 0.0223(4) Uani 1 1 d . . . N6 N 0.74203(12) 0.32353(10) 0.22920(11) 0.0198(4) Uani 1 1 d . . . O1 O 0.94902(11) 0.55818(9) 0.40214(11) 0.0323(4) Uani 1 1 d . . . O2 O 0.61911(10) 0.36887(9) 0.20654(10) 0.0289(4) Uani 1 1 d . . . O3 O 0.83544(9) 0.23275(8) 0.16313(8) 0.0187(4) Uani 1 1 d . . . O4 O 0.87750(9) 0.20308(8) 0.10454(9) 0.0199(4) Uani 1 1 d . . . O5 O 0.89453(9) 0.21076(9) -0.16864(9) 0.0250(4) Uani 1 1 d . . . O6 O 1.24327(10) 0.36142(11) 0.04699(11) 0.0364(5) Uani 1 1 d . . . O7 O 1.08391(9) 0.32366(8) 0.23508(10) 0.0224(4) Uani 1 1 d . . . O8 O 1.03929(9) 0.35769(8) 0.28935(10) 0.0226(4) Uani 1 1 d . . . O1W O 1.04759(11) 0.19824(10) 0.12418(11) 0.0338(4) Uani 1 1 d . . . H5 H 0.992(3) 0.220(3) 0.151(3) 0.115(17) Uiso 1 1 d . . . H3 H 0.9775(17) 0.2136(14) 0.0063(17) 0.025(7) Uiso 1 1 d . . . H1 H 0.793(2) 0.3352(17) 0.2518(19) 0.046(9) Uiso 1 1 d . . . H2 H 0.930(2) 0.411(2) 0.331(2) 0.072(12) Uiso 1 1 d . . . H4 H 1.099(2) 0.2900(19) 0.091(2) 0.064(11) Uiso 1 1 d . . . H6 H 1.056(2) 0.140(2) 0.128(2) 0.066(11) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0171(12) 0.0257(13) 0.0237(12) -0.0041(10) 0.0075(10) 0.0039(9) C2 0.0284(14) 0.0322(14) 0.0227(13) -0.0051(10) 0.0083(10) -0.0001(11) C3 0.0430(17) 0.0406(16) 0.0270(14) -0.0059(12) 0.0170(12) -0.0085(13) C4 0.0323(15) 0.0372(16) 0.0339(15) -0.0124(12) 0.0179(12) -0.0095(12) C5 0.0207(13) 0.0252(13) 0.0284(13) -0.0114(10) 0.0096(10) -0.0011(10) C6 0.0178(13) 0.0320(14) 0.0343(14) -0.0133(11) 0.0122(10) -0.0016(10) C7 0.0164(12) 0.0280(13) 0.0330(14) -0.0080(11) 0.0011(10) 0.0015(10) C8 0.0137(12) 0.0242(13) 0.0234(12) -0.0037(10) 0.0010(9) -0.0032(9) C9 0.0176(12) 0.0225(12) 0.0248(13) -0.0019(10) 0.0006(10) -0.0038(9) C10 0.0220(14) 0.0247(13) 0.0359(15) -0.0056(11) 0.0032(11) 0.0008(10) C11 0.0225(14) 0.0277(14) 0.0417(16) 0.0026(12) -0.0069(12) 0.0020(11) C12 0.0284(14) 0.0295(14) 0.0276(14) 0.0052(11) -0.0036(11) -0.0020(11) C13 0.0232(13) 0.0249(13) 0.0287(13) -0.0021(10) 0.0053(10) -0.0067(10) C14 0.0187(12) 0.0199(12) 0.0257(13) 0.0009(9) 0.0018(10) -0.0038(9) C15 0.0171(12) 0.0205(12) 0.0225(12) -0.0058(9) 0.0029(9) -0.0049(9) C16 0.0139(12) 0.0252(13) 0.0191(12) -0.0026(9) 0.0006(9) -0.0017(9) C17 0.0239(13) 0.0231(13) 0.0223(12) -0.0052(10) 0.0011(10) -0.0004(10) C18 0.0268(14) 0.0176(12) 0.0283(13) -0.0020(10) 0.0017(10) -0.0025(10) C19 0.0284(14) 0.0310(14) 0.0220(12) -0.0010(10) 0.0032(10) -0.0097(11) C20 0.0174(12) 0.0303(14) 0.0235(12) -0.0073(10) 0.0041(10) -0.0048(10) C21 0.0132(12) 0.0225(12) 0.0216(12) -0.0033(9) 0.0002(9) -0.0018(9) C22 0.0213(13) 0.0253(13) 0.0225(12) -0.0025(10) 0.0055(10) -0.0004(10) C23 0.0284(14) 0.0226(13) 0.0209(12) 0.0008(10) 0.0088(10) -0.0025(10) C24 0.0243(13) 0.0247(13) 0.0190(12) 0.0023(10) 0.0048(10) 0.0027(10) C25 0.0331(15) 0.0234(13) 0.0270(13) 0.0004(10) 0.0057(11) 0.0023(11) C26 0.0334(16) 0.0358(16) 0.0396(16) 0.0032(12) 0.0064(12) 0.0153(12) C27 0.0232(14) 0.0405(16) 0.0274(14) 0.0005(11) -0.0009(11) 0.0087(11) C28 0.0202(13) 0.0318(14) 0.0182(12) -0.0016(10) 0.0049(9) 0.0043(10) C29 0.0196(14) 0.0373(14) 0.0119(11) 0.0000(10) 0.0043(9) 0.0028(10) C30 0.0176(12) 0.0265(13) 0.0152(11) 0.0003(9) 0.0031(9) -0.0008(9) C31 0.0108(11) 0.0254(12) 0.0172(11) 0.0007(9) 0.0041(9) -0.0015(9) C32 0.0155(12) 0.0233(12) 0.0189(11) 0.0022(9) -0.0010(9) 0.0003(9) C33 0.0166(12) 0.0307(14) 0.0278(13) 0.0057(10) 0.0039(10) -0.0010(10) C34 0.0188(13) 0.0255(14) 0.0524(17) 0.0134(12) 0.0014(12) -0.0048(10) C35 0.0229(14) 0.0202(13) 0.0493(17) -0.0019(11) 0.0002(12) 0.0010(10) C36 0.0211(13) 0.0203(12) 0.0315(13) -0.0041(10) -0.0011(10) 0.0020(10) C37 0.0173(12) 0.0244(13) 0.0198(12) 0.0007(9) -0.0005(9) 0.0014(9) C38 0.0159(12) 0.0233(12) 0.0150(11) -0.0023(9) -0.0006(9) -0.0009(9) C39 0.0131(11) 0.0210(12) 0.0164(11) -0.0009(9) 0.0018(9) -0.0040(9) C40 0.0180(12) 0.0245(12) 0.0163(11) -0.0013(9) 0.0038(9) 0.0003(9) C41 0.0256(13) 0.0290(13) 0.0174(12) 0.0042(10) 0.0031(10) -0.0008(10) C42 0.0240(13) 0.0252(13) 0.0245(13) 0.0043(10) 0.0020(10) 0.0078(10) C43 0.0198(12) 0.0257(13) 0.0185(12) -0.0018(9) 0.0059(9) 0.0013(10) C44 0.0156(12) 0.0199(12) 0.0163(11) -0.0023(9) 0.0018(9) -0.0036(9) C45 0.0180(12) 0.0240(12) 0.0187(12) -0.0020(9) 0.0029(9) 0.0018(9) C46 0.0140(12) 0.0267(13) 0.0193(12) -0.0024(10) 0.0037(9) 0.0058(9) N1 0.0156(11) 0.0313(12) 0.0185(10) -0.0034(8) 0.0036(9) 0.0012(8) N2 0.0152(10) 0.0265(11) 0.0241(11) -0.0073(8) 0.0050(8) 0.0017(8) N3 0.0211(12) 0.0289(12) 0.0280(12) -0.0125(9) 0.0045(9) -0.0031(9) N4 0.0181(11) 0.0245(11) 0.0256(11) -0.0045(9) 0.0080(8) 0.0008(9) N5 0.0207(11) 0.0307(12) 0.0163(10) -0.0005(8) 0.0058(8) 0.0022(9) N6 0.0176(11) 0.0263(11) 0.0152(10) -0.0025(8) 0.0027(8) 0.0002(8) O1 0.0317(10) 0.0256(10) 0.0371(10) -0.0071(8) 0.0018(8) 0.0004(8) O2 0.0185(10) 0.0385(11) 0.0292(10) -0.0086(8) 0.0039(7) 0.0011(7) O3 0.0148(8) 0.0296(9) 0.0121(8) -0.0039(6) 0.0037(6) -0.0013(6) O4 0.0169(8) 0.0301(9) 0.0131(8) -0.0033(6) 0.0038(6) -0.0004(7) O5 0.0194(9) 0.0388(10) 0.0157(9) -0.0040(7) 0.0014(7) -0.0014(7) O6 0.0222(10) 0.0542(13) 0.0356(11) -0.0180(9) 0.0122(8) -0.0114(9) O7 0.0179(9) 0.0223(9) 0.0273(9) -0.0094(7) 0.0056(7) -0.0038(6) O8 0.0151(8) 0.0256(9) 0.0281(9) -0.0089(7) 0.0070(7) -0.0038(6) O1W 0.0341(11) 0.0335(11) 0.0325(10) -0.0035(8) 0.0045(8) -0.0018(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N2 1.334(3) . ? C1 C2 1.379(3) . ? C1 C46 1.511(3) . ? C2 C3 1.375(4) . ? C2 H2A 0.9500 . ? C3 C4 1.378(4) . ? C3 H3A 0.9500 . ? C4 C5 1.378(4) . ? C4 H4A 0.9500 . ? C5 N2 1.340(3) . ? C5 C6 1.500(4) . ? C6 O6 1.225(3) . ? C6 N3 1.348(3) . ? C7 N3 1.442(3) . ? C7 C8 1.508(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 O7 1.465(3) . ? C8 C21 1.507(3) . ? C8 C9 1.522(3) . ? C9 C10 1.383(3) . ? C9 C14 1.394(3) . ? C10 C11 1.398(4) . ? C10 H10A 0.9500 . ? C11 C12 1.368(4) . ? C11 H11A 0.9500 . ? C12 C13 1.384(4) . ? C12 H12A 0.9500 . ? C13 C14 1.392(3) . ? C13 H13A 0.9500 . ? C14 C15 1.496(3) . ? C15 O8 1.474(3) . ? C15 C16 1.503(3) . ? C15 C22 1.526(3) . ? C16 C17 1.375(3) . ? C16 C21 1.397(3) . ? C17 C18 1.391(3) . ? C17 H17A 0.9500 . ? C18 C19 1.378(4) . ? C18 H18A 0.9500 . ? C19 C20 1.382(4) . ? C19 H19A 0.9500 . ? C20 C21 1.390(3) . ? C20 H20A 0.9500 . ? C22 N4 1.448(3) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 O1 1.227(3) . ? C23 N4 1.327(3) . ? C23 C24 1.506(4) . ? C24 N5 1.325(3) . ? C24 C25 1.403(3) . ? C25 C26 1.386(4) . ? C25 H25A 0.9500 . ? C26 C27 1.366(4) . ? C26 H26A 0.9500 . ? C27 C28 1.399(4) . ? C27 H27A 0.9500 . ? C28 N5 1.333(3) . ? C28 C29 1.509(4) . ? C29 O2 1.220(3) . ? C29 N6 1.335(3) . ? C30 N6 1.445(3) . ? C30 C31 1.522(3) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 O3 1.462(3) . ? C31 C32 1.511(3) . ? C31 C44 1.512(3) . ? C32 C33 1.382(3) . ? C32 C37 1.388(3) . ? C33 C34 1.377(4) . ? C33 H33A 0.9500 . ? C34 C35 1.381(4) . ? C34 H34A 0.9500 . ? C35 C36 1.382(4) . ? C35 H35A 0.9500 . ? C36 C37 1.392(3) . ? C36 H36A 0.9500 . ? C37 C38 1.508(3) . ? C38 O4 1.469(3) . ? C38 C45 1.515(3) . ? C38 C39 1.518(3) . ? C39 C40 1.384(3) . ? C39 C44 1.395(3) . ? C40 C41 1.372(3) . ? C40 H40A 0.9500 . ? C41 C42 1.375(3) . ? C41 H41A 0.9500 . ? C42 C43 1.382(3) . ? C42 H42A 0.9500 . ? C43 C44 1.376(3) . ? C43 H43A 0.9500 . ? C45 N1 1.447(3) . ? C45 H45A 0.9900 . ? C45 H45B 0.9900 . ? C46 O5 1.224(3) . ? C46 N1 1.335(3) . ? N1 H3 0.92(3) . ? N3 H4 0.99(4) . ? N4 H2 0.89(4) . ? N6 H1 0.92(3) . ? O3 O4 1.472(2) . ? O7 O8 1.478(2) . ? O1W H5 1.22(5) . ? O1W H6 1.11(4) . ? 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 C1 C2 123.6(2) . . ? N2 C1 C46 116.5(2) . . ? C2 C1 C46 119.9(2) . . ? C3 C2 C1 118.1(2) . . ? C3 C2 H2A 120.9 . . ? C1 C2 H2A 120.9 . . ? C2 C3 C4 119.4(2) . . ? C2 C3 H3A 120.3 . . ? C4 C3 H3A 120.3 . . ? C5 C4 C3 118.7(2) . . ? C5 C4 H4A 120.7 . . ? C3 C4 H4A 120.7 . . ? N2 C5 C4 122.8(2) . . ? N2 C5 C6 117.1(2) . . ? C4 C5 C6 120.1(2) . . ? O6 C6 N3 123.7(2) . . ? O6 C6 C5 121.6(2) . . ? N3 C6 C5 114.7(2) . . ? N3 C7 C8 114.3(2) . . ? N3 C7 H7A 108.7 . . ? C8 C7 H7A 108.7 . . ? N3 C7 H7B 108.7 . . ? C8 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? O7 C8 C21 106.84(18) . . ? O7 C8 C7 103.20(17) . . ? C21 C8 C7 117.8(2) . . ? O7 C8 C9 105.40(18) . . ? C21 C8 C9 108.17(19) . . ? C7 C8 C9 114.3(2) . . ? C10 C9 C14 120.8(2) . . ? C10 C9 C8 127.3(2) . . ? C14 C9 C8 111.9(2) . . ? C9 C10 C11 118.6(2) . . ? C9 C10 H10A 120.7 . . ? C11 C10 H10A 120.7 . . ? C12 C11 C10 120.7(2) . . ? C12 C11 H11A 119.6 . . ? C10 C11 H11A 119.6 . . ? C11 C12 C13 120.8(2) . . ? C11 C12 H12A 119.6 . . ? C13 C12 H12A 119.6 . . ? C12 C13 C14 119.3(2) . . ? C12 C13 H13A 120.4 . . ? C14 C13 H13A 120.4 . . ? C13 C14 C9 119.7(2) . . ? C13 C14 C15 128.1(2) . . ? C9 C14 C15 112.2(2) . . ? O8 C15 C14 106.35(18) . . ? O8 C15 C16 107.03(17) . . ? C14 C15 C16 109.27(19) . . ? O8 C15 C22 102.73(17) . . ? C14 C15 C22 112.65(19) . . ? C16 C15 C22 117.9(2) . . ? C17 C16 C21 120.4(2) . . ? C17 C16 C15 128.1(2) . . ? C21 C16 C15 111.5(2) . . ? C16 C17 C18 118.9(2) . . ? C16 C17 H17A 120.5 . . ? C18 C17 H17A 120.5 . . ? C19 C18 C17 120.7(2) . . ? C19 C18 H18A 119.7 . . ? C17 C18 H18A 119.7 . . ? C18 C19 C20 120.9(2) . . ? C18 C19 H19A 119.5 . . ? C20 C19 H19A 119.5 . . ? C19 C20 C21 118.6(2) . . ? C19 C20 H20A 120.7 . . ? C21 C20 H20A 120.7 . . ? C20 C21 C16 120.5(2) . . ? C20 C21 C8 126.9(2) . . ? C16 C21 C8 112.6(2) . . ? N4 C22 C15 112.76(19) . . ? N4 C22 H22A 109.0 . . ? C15 C22 H22A 109.0 . . ? N4 C22 H22B 109.0 . . ? C15 C22 H22B 109.0 . . ? H22A C22 H22B 107.8 . . ? O1 C23 N4 123.8(2) . . ? O1 C23 C24 121.6(2) . . ? N4 C23 C24 114.6(2) . . ? N5 C24 C25 123.4(2) . . ? N5 C24 C23 117.0(2) . . ? C25 C24 C23 119.6(2) . . ? C26 C25 C24 117.1(2) . . ? C26 C25 H25A 121.4 . . ? C24 C25 H25A 121.4 . . ? C27 C26 C25 120.0(2) . . ? C27 C26 H26A 120.0 . . ? C25 C26 H26A 120.0 . . ? C26 C27 C28 118.8(2) . . ? C26 C27 H27A 120.6 . . ? C28 C27 H27A 120.6 . . ? N5 C28 C27 122.1(2) . . ? N5 C28 C29 118.2(2) . . ? C27 C28 C29 119.6(2) . . ? O2 C29 N6 124.7(2) . . ? O2 C29 C28 120.6(2) . . ? N6 C29 C28 114.7(2) . . ? N6 C30 C31 113.66(18) . . ? N6 C30 H30A 108.8 . . ? C31 C30 H30A 108.8 . . ? N6 C30 H30B 108.8 . . ? C31 C30 H30B 108.8 . . ? H30A C30 H30B 107.7 . . ? O3 C31 C32 107.09(17) . . ? O3 C31 C44 107.23(17) . . ? C32 C31 C44 107.37(18) . . ? O3 C31 C30 102.82(17) . . ? C32 C31 C30 113.92(18) . . ? C44 C31 C30 117.66(19) . . ? C33 C32 C37 120.1(2) . . ? C33 C32 C31 127.6(2) . . ? C37 C32 C31 112.28(19) . . ? C34 C33 C32 119.5(2) . . ? C34 C33 H33A 120.2 . . ? C32 C33 H33A 120.2 . . ? C33 C34 C35 120.7(2) . . ? C33 C34 H34A 119.6 . . ? C35 C34 H34A 119.6 . . ? C34 C35 C36 120.3(2) . . ? C34 C35 H35A 119.9 . . ? C36 C35 H35A 119.9 . . ? C35 C36 C37 119.1(2) . . ? C35 C36 H36A 120.4 . . ? C37 C36 H36A 120.4 . . ? C32 C37 C36 120.2(2) . . ? C32 C37 C38 112.1(2) . . ? C36 C37 C38 127.7(2) . . ? O4 C38 C37 105.99(17) . . ? O4 C38 C45 103.53(17) . . ? C37 C38 C45 114.56(19) . . ? O4 C38 C39 107.56(17) . . ? C37 C38 C39 107.15(18) . . ? C45 C38 C39 117.23(19) . . ? C40 C39 C44 120.2(2) . . ? C40 C39 C38 127.5(2) . . ? C44 C39 C38 112.15(19) . . ? C41 C40 C39 118.8(2) . . ? C41 C40 H40A 120.6 . . ? C39 C40 H40A 120.6 . . ? C40 C41 C42 121.1(2) . . ? C40 C41 H41A 119.5 . . ? C42 C41 H41A 119.5 . . ? C41 C42 C43 120.5(2) . . ? C41 C42 H42A 119.7 . . ? C43 C42 H42A 119.7 . . ? C44 C43 C42 119.0(2) . . ? C44 C43 H43A 120.5 . . ? C42 C43 H43A 120.5 . . ? C43 C44 C39 120.2(2) . . ? C43 C44 C31 128.0(2) . . ? C39 C44 C31 111.72(19) . . ? N1 C45 C38 113.71(19) . . ? N1 C45 H45A 108.8 . . ? C38 C45 H45A 108.8 . . ? N1 C45 H45B 108.8 . . ? C38 C45 H45B 108.8 . . ? H45A C45 H45B 107.7 . . ? O5 C46 N1 124.3(2) . . ? O5 C46 C1 121.1(2) . . ? N1 C46 C1 114.6(2) . . ? C46 N1 C45 123.0(2) . . ? C46 N1 H3 114.9(16) . . ? C45 N1 H3 120.1(16) . . ? C1 N2 C5 117.4(2) . . ? C6 N3 C7 123.3(2) . . ? C6 N3 H4 113(2) . . ? C7 N3 H4 124(2) . . ? C23 N4 C22 122.7(2) . . ? C23 N4 H2 121(3) . . ? C22 N4 H2 115(3) . . ? C24 N5 C28 118.5(2) . . ? C29 N6 C30 122.3(2) . . ? C29 N6 H1 115(2) . . ? C30 N6 H1 122(2) . . ? C31 O3 O4 110.76(14) . . ? C38 O4 O3 111.39(14) . . ? C8 O7 O8 111.53(14) . . ? C15 O8 O7 110.25(14) . . ? H5 O1W H6 114(3) . . ? loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.011 0.501 -0.027 2324 1178 ' ' _platon_squeeze_details ; ; _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.358 _refine_diff_density_min -0.339 _refine_diff_density_rms 0.071 _vrf_CHEMW03_jjg_sq ; PROBLEM: ALERT: The ratio of given/expected molecular weight as RESPONSE: Use of Platon SQUEEZE to remove disordered solvent ; _vrf_PLAT355_jjg_sq ; PROBLEM: Long O-H Bond (0.82A) O1W - H5 ... 1.23 Ang. RESPONSE: Hydrogen is a component of solvent water. There appears to be an O---H bond between the endoperoxide oxygen and the hydrogen, possibly acidifying and elongating that bond. The other hydrogen of the water appears to form a bond between a proximal macrocyclic amide. ; _vrf_PLAT043_jjg_sq ; PROBLEM: Check Reported Molecular Weight ................ 1296.30 RESPONSE: Use of Platon SQUEEZE to remove disordered solvent ; _vrf_PLAT044_jjg_sq ; PROBLEM: Calculated and Reported Dx Differ .............. ? RESPONSE: Use of Platon SQUEEZE to remove disordered solvent ; _vrf_PLAT051_jjg_sq ; PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by . 89.49 Perc. RESPONSE: Use of Platon SQUEEZE to remove disordered solvent ; # Attachment 'macrocycle_1a.cif' data_new1 _database_code_depnum_ccdc_archive 'CCDC 717859' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C56 H52 N4 O4, 2(C4 H8 O2), C H Cl3' _chemical_formula_sum 'C65 H69 Cl3 N4 O8' _chemical_formula_weight 1140.59 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'p -1' _symmetry_space_group_name_Hall '-p 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.5937(5) _cell_length_b 13.2158(5) _cell_length_c 18.7174(8) _cell_angle_alpha 73.655(2) _cell_angle_beta 88.986(2) _cell_angle_gamma 79.997(2) _cell_volume 2942.3(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7682 _cell_measurement_theta_min 1.13 _cell_measurement_theta_max 26.500 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.287 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1204 _exptl_absorpt_coefficient_mu 0.215 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9231 _exptl_absorpt_correction_T_max 0.9564 _exptl_absorpt_process_details ; Blessing, R. H. (1995) Acta Cryst. A51, 33-38. Sheldrick, G. M. (2004) SADABS University of G\"ottingen, Germany. ; _exptl_special_details ; One molecule of disordered chloroform is present. Two atoms of chlorine were modeled with ISOR= 0.003. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_source_type 'Siemens KFFMO2K-90' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker d8-APEX II CCD diffractometer' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.33 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 44027 _diffrn_reflns_av_R_equivalents 0.0465 _diffrn_reflns_av_sigmaI/netI 0.0498 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.13 _diffrn_reflns_theta_max 25.35 _reflns_number_total 10733 _reflns_number_gt 7239 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_cell_refinement 'APEX2/SAINT (Bruker, 2004)' _computing_data_reduction 'SAINT/XPREP (Bruker, 2004; Sheldrick, 2003)' _computing_structure_solution 'XS (Sheldrick, 2001)' _computing_structure_refinement 'XL (Sheldrick, 2001)' _computing_molecular_graphics 'XP (Sheldrick, 1998)' _computing_publication_material 'enCIFer (CCDC, 2004)' _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^)+(0.0715P)^2^+5.7501P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10733 _refine_ls_number_parameters 755 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.1071 _refine_ls_R_factor_gt 0.0649 _refine_ls_wR_factor_ref 0.1952 _refine_ls_wR_factor_gt 0.1657 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.091 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C9S C 0.3978(4) 0.3558(4) 0.1448(3) 0.0490(12) Uani 1 1 d . . . Cl1 Cl 0.3816(2) 0.47138(13) 0.06646(12) 0.0747(7) Uani 0.767(3) 1 d P A 1 Cl2 Cl 0.27279(12) 0.31342(17) 0.16873(11) 0.0691(6) Uani 0.767(3) 1 d P A 1 Cl3 Cl 0.48981(10) 0.25383(11) 0.12669(8) 0.0410(4) Uani 0.767(3) 1 d P A 1 Cl1X Cl 0.3097(8) 0.4543(8) 0.1239(8) 0.134(4) Uani 0.233(3) 1 d P A 2 Cl2X Cl 0.485(2) 0.369(2) 0.0732(16) 0.313(13) Uani 0.233(3) 1 d PU A 2 Cl3X Cl 0.360(2) 0.228(2) 0.1641(16) 0.322(13) Uani 0.233(3) 1 d PU A 2 C32 C 1.0681(3) 1.1652(3) 0.0955(3) 0.0484(12) Uani 1 1 d . . . H32A H 1.1244 1.2096 0.0862 0.073 Uiso 1 1 calc R . . H32B H 1.0286 1.1742 0.1395 0.073 Uiso 1 1 calc R . . H32C H 1.0181 1.1870 0.0522 0.073 Uiso 1 1 calc R . . C5S C 0.7702(3) 0.6406(4) 0.4458(2) 0.0406(10) Uani 1 1 d . . . H5SA H 0.6998 0.6390 0.4252 0.061 Uiso 1 1 calc R . . H5SB H 0.7611 0.6885 0.4779 0.061 Uiso 1 1 calc R . . H5SC H 0.8028 0.5682 0.4752 0.061 Uiso 1 1 calc R . . C33 C 1.1826(3) 1.0370(3) 0.0405(2) 0.0424(10) Uani 1 1 d . . . H33A H 1.2361 1.0845 0.0310 0.064 Uiso 1 1 calc R . . H33B H 1.1328 1.0565 -0.0028 0.064 Uiso 1 1 calc R . . H33C H 1.2192 0.9626 0.0492 0.064 Uiso 1 1 calc R . . C31 C 1.1981(3) 1.0144(3) 0.1765(2) 0.0366(9) Uani 1 1 d . . . H31A H 1.2524 1.0610 0.1680 0.055 Uiso 1 1 calc R . . H31B H 1.2337 0.9400 0.1838 0.055 Uiso 1 1 calc R . . H31C H 1.1581 1.0204 0.2210 0.055 Uiso 1 1 calc R . . C1S C 0.7225(3) 0.6692(3) 0.0671(2) 0.0319(9) Uani 1 1 d . . . H1SA H 0.7160 0.6730 0.0142 0.048 Uiso 1 1 calc R . . H1SB H 0.7985 0.6471 0.0837 0.048 Uiso 1 1 calc R . . H1SC H 0.6949 0.7397 0.0739 0.048 Uiso 1 1 calc R . . C1 C 0.2488(3) -0.0321(3) 0.4337(2) 0.0348(9) Uani 1 1 d . . . H1A H 0.1939 -0.0771 0.4507 0.052 Uiso 1 1 calc R . . H1B H 0.3090 -0.0543 0.4704 0.052 Uiso 1 1 calc R . . H1C H 0.2751 -0.0402 0.3856 0.052 Uiso 1 1 calc R . . C3S C 0.6347(3) 0.5328(3) 0.3161(2) 0.0332(9) Uani 1 1 d . . . H3SA H 0.5921 0.4872 0.3513 0.050 Uiso 1 1 calc R . . H3SB H 0.6133 0.6072 0.3175 0.050 Uiso 1 1 calc R . . H3SC H 0.7115 0.5085 0.3299 0.050 Uiso 1 1 calc R . . C2 C 0.1044(3) 0.1183(3) 0.3680(2) 0.0357(9) Uani 1 1 d . . . H2A H 0.0720 0.1933 0.3619 0.054 Uiso 1 1 calc R . . H2B H 0.0502 0.0727 0.3857 0.054 Uiso 1 1 calc R . . H2C H 0.1304 0.1097 0.3200 0.054 Uiso 1 1 calc R . . C20 C 0.4908(3) 0.7760(3) 0.4490(2) 0.0330(9) Uani 1 1 d . . . H20A H 0.5192 0.7891 0.4916 0.040 Uiso 1 1 calc R . . C7S C 1.0172(3) 0.7242(3) 0.3571(2) 0.0375(10) Uani 1 1 d . . . H7SA H 1.0068 0.7056 0.3103 0.045 Uiso 1 1 calc R . . H7SB H 1.0910 0.6902 0.3774 0.045 Uiso 1 1 calc R . . C3 C 0.1580(3) 0.0958(3) 0.5007(2) 0.0350(9) Uani 1 1 d . . . H3A H 0.1259 0.1706 0.4960 0.053 Uiso 1 1 calc R . . H3B H 0.2183 0.0731 0.5373 0.053 Uiso 1 1 calc R . . H3C H 0.1034 0.0503 0.5172 0.053 Uiso 1 1 calc R . . C21 C 0.4201(3) 0.7015(3) 0.4578(2) 0.0325(9) Uani 1 1 d . . . H21A H 0.4011 0.6648 0.5064 0.039 Uiso 1 1 calc R . . C41 C 0.9203(3) 0.3800(3) 0.4328(2) 0.0309(9) Uani 1 1 d . . . H41A H 0.9447 0.4059 0.4709 0.037 Uiso 1 1 calc R . . C2S C 0.6579(3) 0.5885(3) 0.1123(2) 0.0264(8) Uani 1 1 d . . . H2SA H 0.5808 0.6098 0.0961 0.032 Uiso 1 1 calc R . . H2SB H 0.6849 0.5167 0.1059 0.032 Uiso 1 1 calc R . . C6S C 0.8419(3) 0.6802(3) 0.3838(2) 0.0281(8) Uani 1 1 d . . . C4S C 0.6150(3) 0.5262(3) 0.2397(2) 0.0258(8) Uani 1 1 d . . . C8S C 1.0057(4) 0.8430(4) 0.3409(2) 0.0473(11) Uani 1 1 d . . . H8SA H 1.0593 0.8688 0.3049 0.071 Uiso 1 1 calc R . . H8SB H 1.0170 0.8613 0.3870 0.071 Uiso 1 1 calc R . . H8SC H 0.9331 0.8768 0.3200 0.071 Uiso 1 1 calc R . . C200 C 0.1992(3) 0.0856(3) 0.4249(2) 0.0264(8) Uani 1 1 d . . . C42 C 0.8525(3) 0.3013(3) 0.4505(2) 0.0303(8) Uani 1 1 d . . . H42A H 0.8321 0.2746 0.5004 0.036 Uiso 1 1 calc R . . C13 C 0.4001(3) 0.7854(3) 0.0550(2) 0.0275(8) Uani 1 1 d . . . H13A H 0.3756 0.7688 0.0127 0.033 Uiso 1 1 calc R . . C43 C 0.8170(3) 0.2642(3) 0.3964(2) 0.0263(8) Uani 1 1 d . . . H43A H 0.7725 0.2111 0.4093 0.032 Uiso 1 1 calc R . . C22 C 0.3794(3) 0.6821(3) 0.3973(2) 0.0284(8) Uani 1 1 d . . . H22A H 0.3314 0.6323 0.4043 0.034 Uiso 1 1 calc R . . C19 C 0.5181(3) 0.8289(3) 0.3798(2) 0.0273(8) Uani 1 1 d . . . H19A H 0.5649 0.8795 0.3749 0.033 Uiso 1 1 calc R . . C14 C 0.4706(3) 0.8610(3) 0.0460(2) 0.0272(8) Uani 1 1 d . . . H14A H 0.4935 0.8942 -0.0023 0.033 Uiso 1 1 calc R . . C9 C 0.2817(3) 0.6432(3) 0.2702(2) 0.0242(8) Uani 1 1 d . . . H9A H 0.2299 0.6608 0.3071 0.029 Uiso 1 1 calc R . . H9B H 0.2414 0.6591 0.2222 0.029 Uiso 1 1 calc R . . C49 C 0.8752(3) 0.4089(3) 0.0390(2) 0.0272(8) Uani 1 1 d . . . H49A H 0.8902 0.4407 -0.0114 0.033 Uiso 1 1 calc R . . C50 C 0.8061(3) 0.3329(3) 0.0562(2) 0.0262(8) Uani 1 1 d . . . H50A H 0.7750 0.3136 0.0172 0.031 Uiso 1 1 calc R . . C52 C 0.7424(3) 0.1763(3) 0.2840(2) 0.0230(7) Uani 1 1 d . . . H52A H 0.7414 0.1449 0.2419 0.028 Uiso 1 1 calc R . . H52B H 0.7778 0.1195 0.3276 0.028 Uiso 1 1 calc R . . C11 C 0.3675(3) 0.7371(3) 0.1236(2) 0.0242(8) Uani 1 1 d . . . H11A H 0.3209 0.6863 0.1285 0.029 Uiso 1 1 calc R . . C30 C 1.1196(3) 1.0485(3) 0.1089(2) 0.0249(8) Uani 1 1 d . . . C40 C 0.9501(3) 0.4181(3) 0.3618(2) 0.0254(8) Uani 1 1 d . . . H40A H 0.9958 0.4703 0.3509 0.031 Uiso 1 1 calc R . . C27 C 0.9266(3) 1.0091(3) 0.13469(18) 0.0208(7) Uani 1 1 d . . . H27A H 0.9019 1.0829 0.1299 0.025 Uiso 1 1 calc R . . C100 C 1.0304(3) 0.4908(3) 0.2120(2) 0.0216(7) Uani 1 1 d . . . H10A H 1.0812 0.4709 0.2555 0.026 Uiso 1 1 calc R . . H10B H 1.0719 0.4777 0.1691 0.026 Uiso 1 1 calc R . . C24 C 0.5735(3) 0.9522(3) 0.2307(2) 0.0229(7) Uani 1 1 d . . . H24A H 0.5405 1.0138 0.1890 0.027 Uiso 1 1 calc R . . H24B H 0.5716 0.9766 0.2762 0.027 Uiso 1 1 calc R . . C48 C 0.9208(3) 0.4370(3) 0.09451(19) 0.0225(7) Uani 1 1 d . . . H48A H 0.9672 0.4885 0.0820 0.027 Uiso 1 1 calc R . . C51 C 0.7835(3) 0.2872(3) 0.1278(2) 0.0238(8) Uani 1 1 d . . . H51A H 0.7361 0.2365 0.1380 0.029 Uiso 1 1 calc R . . C15 C 0.5052(3) 0.8857(3) 0.10603(19) 0.0238(8) Uani 1 1 d . . . H15A H 0.5520 0.9366 0.0990 0.029 Uiso 1 1 calc R . . C4 C 0.2813(3) 0.1607(3) 0.39823(19) 0.0210(7) Uani 1 1 d . . . C23 C 0.4068(3) 0.7347(3) 0.32335(19) 0.0216(7) Uani 1 1 d . . . C44 C 0.8448(3) 0.3030(3) 0.32029(19) 0.0215(7) Uani 1 1 d . . . C35 C 0.9953(3) 0.7938(3) 0.14639(18) 0.0189(7) Uani 1 1 d . . . C7 C 0.4251(2) 0.3043(3) 0.34652(18) 0.0184(7) Uani 1 1 d . . . H7A H 0.4739 0.3526 0.3292 0.022 Uiso 1 1 calc R . . C34 C 1.0671(3) 0.8656(3) 0.12899(18) 0.0202(7) Uani 1 1 d . . . H34A H 1.1401 0.8401 0.1203 0.024 Uiso 1 1 calc R . . C55 C 0.3886(3) 0.1239(3) 0.38598(18) 0.0198(7) Uani 1 1 d . . . H55A H 0.4135 0.0491 0.3954 0.024 Uiso 1 1 calc R . . C26 C 0.8537(2) 0.9380(3) 0.15231(18) 0.0186(7) Uani 1 1 d . . . C5 C 0.2476(3) 0.2707(3) 0.38454(18) 0.0202(7) Uani 1 1 d . . . H5A H 0.1750 0.2973 0.3932 0.024 Uiso 1 1 calc R . . C6 C 0.3180(3) 0.3431(3) 0.35839(18) 0.0184(7) Uani 1 1 d . . . C53 C 0.5747(2) 0.1484(3) 0.34834(18) 0.0174(7) Uani 1 1 d . . . C36 C 1.0390(3) 0.6792(3) 0.15220(18) 0.0191(7) Uani 1 1 d . . . C28 C 1.0352(3) 0.9738(3) 0.12393(19) 0.0207(7) Uani 1 1 d . . . C54 C 0.4602(2) 0.1951(3) 0.36009(17) 0.0181(7) Uani 1 1 d . . . C38 C 0.9454(2) 0.4200(2) 0.22872(19) 0.0194(7) Uani 1 1 d . . . C16 C 0.4732(2) 0.8371(2) 0.17996(18) 0.0189(7) Uani 1 1 d . . . C39 C 0.9145(2) 0.3816(3) 0.30263(19) 0.0207(7) Uani 1 1 d . . . C17 C 0.5076(2) 0.8641(2) 0.24209(19) 0.0197(7) Uani 1 1 d . . . C29 C 0.8880(3) 0.8304(3) 0.15894(18) 0.0192(7) Uani 1 1 d . . . H29A H 0.8387 0.7818 0.1720 0.023 Uiso 1 1 calc R . . C45 C 0.8070(2) 0.2666(2) 0.26348(19) 0.0193(7) Uani 1 1 d . . . C46 C 0.8290(2) 0.3128(2) 0.18882(19) 0.0189(7) Uani 1 1 d . . . C18 C 0.4787(2) 0.8111(2) 0.31425(19) 0.0201(7) Uani 1 1 d . . . C10 C 0.4015(2) 0.7605(2) 0.18882(19) 0.0200(7) Uani 1 1 d . . . C25 C 0.7381(2) 0.9822(3) 0.16237(18) 0.0184(7) Uani 1 1 d . . . C47 C 0.9002(2) 0.3908(2) 0.17121(19) 0.0194(7) Uani 1 1 d . . . C12 C 0.3666(3) 0.7137(2) 0.26035(19) 0.0207(7) Uani 1 1 d . . . C8 C 0.2730(3) 0.4595(3) 0.34252(18) 0.0187(7) Uani 1 1 d . . . N2 N 0.6315(2) 0.2141(2) 0.30161(16) 0.0222(6) Uani 1 1 d . . . H2D H 0.6015 0.2813 0.2811 0.027 Uiso 1 1 calc R . . N3 N 0.9849(2) 0.6048(2) 0.19508(15) 0.0205(6) Uani 1 1 d . . . H3D H 0.9222 0.6253 0.2128 0.025 Uiso 1 1 calc R . . O2S O 0.8179(2) 0.7058(2) 0.31821(14) 0.0359(6) Uani 1 1 d . . . N1 N 0.3264(2) 0.5292(2) 0.29477(16) 0.0218(6) Uani 1 1 d . . . H1D H 0.3890 0.5054 0.2783 0.026 Uiso 1 1 calc R . . O1S O 0.93922(19) 0.6834(2) 0.41021(14) 0.0330(6) Uani 1 1 d . . . N4 N 0.6859(2) 0.9179(2) 0.21437(15) 0.0206(6) Uani 1 1 d . . . H4A H 0.7200 0.8540 0.2391 0.025 Uiso 1 1 calc R . . O4S O 0.55459(19) 0.4724(2) 0.22381(14) 0.0313(6) Uani 1 1 d . . . O2 O 0.61304(18) 0.05475(18) 0.37904(14) 0.0272(6) Uani 1 1 d . . . O3 O 1.12230(18) 0.65265(18) 0.12144(13) 0.0252(5) Uani 1 1 d . . . O4 O 0.69498(18) 1.07194(17) 0.12527(13) 0.0246(5) Uani 1 1 d . . . O3S O 0.67074(18) 0.58668(19) 0.18968(14) 0.0277(6) Uani 1 1 d . . . O1 O 0.18915(18) 0.49122(18) 0.37110(13) 0.0249(5) Uani 1 1 d . . . H1S H 0.431(4) 0.374(4) 0.188(3) 0.075(16) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C9S 0.049(3) 0.046(3) 0.058(3) -0.028(2) -0.007(2) -0.003(2) Cl1 0.1063(17) 0.0339(9) 0.0779(14) -0.0083(8) -0.0443(12) -0.0045(9) Cl2 0.0311(8) 0.1032(15) 0.0959(14) -0.0667(12) 0.0080(8) -0.0094(8) Cl3 0.0321(7) 0.0379(8) 0.0547(9) -0.0206(6) 0.0038(6) 0.0016(6) Cl1X 0.101(7) 0.093(7) 0.201(12) -0.046(7) -0.014(8) 0.010(5) Cl2X 0.312(13) 0.315(13) 0.314(13) -0.092(5) 0.010(3) -0.054(4) Cl3X 0.323(13) 0.321(13) 0.324(13) -0.091(5) 0.006(3) -0.059(4) C32 0.023(2) 0.020(2) 0.104(4) -0.016(2) 0.007(2) -0.0112(16) C5S 0.038(2) 0.050(3) 0.035(2) -0.0128(19) 0.0063(18) -0.012(2) C33 0.043(2) 0.042(2) 0.047(3) -0.010(2) 0.016(2) -0.026(2) C31 0.031(2) 0.035(2) 0.050(3) -0.0132(19) -0.0010(18) -0.0170(17) C1S 0.026(2) 0.0251(19) 0.042(2) -0.0055(17) 0.0046(17) -0.0066(16) C1 0.0202(19) 0.0223(19) 0.062(3) -0.0086(18) 0.0087(18) -0.0109(15) C3S 0.025(2) 0.033(2) 0.041(2) -0.0087(17) 0.0042(17) -0.0048(16) C2 0.0218(19) 0.029(2) 0.059(3) -0.0123(18) -0.0018(18) -0.0117(16) C20 0.032(2) 0.037(2) 0.031(2) -0.0146(17) 0.0046(17) -0.0017(17) C7S 0.029(2) 0.056(3) 0.033(2) -0.0186(19) 0.0076(17) -0.0115(19) C3 0.031(2) 0.028(2) 0.047(2) -0.0074(17) 0.0145(18) -0.0134(17) C21 0.033(2) 0.030(2) 0.030(2) -0.0048(16) 0.0120(17) -0.0022(17) C41 0.027(2) 0.035(2) 0.031(2) -0.0094(17) -0.0064(16) -0.0042(16) C2S 0.0192(18) 0.0248(19) 0.033(2) -0.0054(15) -0.0017(15) -0.0028(14) C6S 0.029(2) 0.027(2) 0.028(2) -0.0083(16) -0.0001(16) -0.0039(15) C4S 0.0177(17) 0.0181(17) 0.038(2) -0.0046(15) 0.0040(15) 0.0010(14) C8S 0.049(3) 0.056(3) 0.043(3) -0.016(2) 0.008(2) -0.024(2) C200 0.0172(17) 0.0228(18) 0.040(2) -0.0084(16) 0.0050(15) -0.0077(14) C42 0.0234(19) 0.035(2) 0.027(2) -0.0005(16) -0.0001(15) -0.0030(16) C13 0.0225(18) 0.0265(19) 0.033(2) -0.0085(16) -0.0039(15) -0.0021(15) C43 0.0179(17) 0.0257(19) 0.031(2) -0.0012(15) -0.0003(15) -0.0027(14) C22 0.0260(19) 0.0247(19) 0.033(2) -0.0063(16) 0.0105(16) -0.0040(15) C19 0.0217(18) 0.0238(19) 0.038(2) -0.0126(16) 0.0039(16) -0.0016(15) C14 0.0211(18) 0.0267(19) 0.030(2) -0.0028(15) 0.0015(15) -0.0027(15) C9 0.0165(17) 0.0163(17) 0.037(2) -0.0019(14) 0.0012(15) -0.0040(13) C49 0.0221(18) 0.0281(19) 0.031(2) -0.0084(16) 0.0083(15) -0.0040(15) C50 0.0196(18) 0.0280(19) 0.035(2) -0.0157(16) 0.0005(15) -0.0022(15) C52 0.0143(16) 0.0176(17) 0.037(2) -0.0072(15) 0.0056(14) -0.0041(13) C11 0.0168(17) 0.0181(17) 0.038(2) -0.0079(15) -0.0004(15) -0.0026(14) C30 0.0187(17) 0.0160(17) 0.041(2) -0.0073(15) 0.0025(15) -0.0077(14) C40 0.0189(17) 0.0223(18) 0.035(2) -0.0070(15) -0.0040(15) -0.0034(14) C27 0.0212(17) 0.0172(17) 0.0248(18) -0.0065(14) 0.0012(14) -0.0046(13) C100 0.0134(16) 0.0186(17) 0.033(2) -0.0068(14) 0.0030(14) -0.0055(13) C24 0.0170(17) 0.0200(17) 0.034(2) -0.0109(15) 0.0069(14) -0.0044(14) C48 0.0161(17) 0.0175(17) 0.034(2) -0.0071(14) 0.0081(14) -0.0033(13) C51 0.0158(17) 0.0205(17) 0.037(2) -0.0122(15) 0.0036(15) -0.0027(14) C15 0.0141(16) 0.0193(17) 0.033(2) -0.0007(15) 0.0022(14) -0.0013(13) C4 0.0150(16) 0.0204(17) 0.0283(19) -0.0081(14) 0.0021(14) -0.0035(13) C23 0.0165(17) 0.0144(16) 0.031(2) -0.0045(14) 0.0065(14) 0.0008(13) C44 0.0134(16) 0.0174(17) 0.030(2) -0.0024(14) -0.0002(14) -0.0007(13) C35 0.0182(17) 0.0186(17) 0.0216(18) -0.0071(13) 0.0005(13) -0.0056(13) C7 0.0148(16) 0.0199(17) 0.0225(18) -0.0061(13) 0.0014(13) -0.0086(13) C34 0.0156(16) 0.0193(17) 0.0254(18) -0.0060(14) 0.0009(13) -0.0028(13) C55 0.0176(17) 0.0157(16) 0.0272(19) -0.0068(14) 0.0019(14) -0.0049(13) C26 0.0152(16) 0.0186(17) 0.0237(18) -0.0076(13) 0.0001(13) -0.0045(13) C5 0.0141(16) 0.0232(18) 0.0253(18) -0.0083(14) 0.0031(13) -0.0062(13) C6 0.0183(17) 0.0187(17) 0.0197(17) -0.0062(13) 0.0015(13) -0.0059(13) C53 0.0145(16) 0.0186(17) 0.0221(17) -0.0079(14) 0.0013(13) -0.0071(13) C36 0.0163(17) 0.0214(17) 0.0226(18) -0.0085(14) -0.0020(14) -0.0075(14) C28 0.0179(17) 0.0176(17) 0.0271(19) -0.0051(14) 0.0015(14) -0.0067(13) C54 0.0160(16) 0.0216(17) 0.0186(17) -0.0064(13) 0.0012(13) -0.0069(13) C38 0.0131(16) 0.0116(15) 0.0316(19) -0.0043(13) 0.0003(14) 0.0003(12) C16 0.0104(15) 0.0154(16) 0.0287(19) -0.0049(13) 0.0025(13) 0.0013(12) C39 0.0130(16) 0.0173(17) 0.030(2) -0.0046(14) -0.0009(14) -0.0016(13) C17 0.0121(16) 0.0152(16) 0.0304(19) -0.0061(14) 0.0030(13) 0.0006(13) C29 0.0158(16) 0.0230(18) 0.0209(18) -0.0061(14) 0.0007(13) -0.0092(14) C45 0.0109(15) 0.0134(16) 0.033(2) -0.0070(14) 0.0042(14) -0.0003(12) C46 0.0095(15) 0.0147(16) 0.032(2) -0.0092(14) 0.0036(13) 0.0015(12) C18 0.0139(16) 0.0153(16) 0.0313(19) -0.0083(14) 0.0035(14) -0.0003(13) C10 0.0114(15) 0.0136(16) 0.032(2) -0.0049(14) 0.0015(13) 0.0039(12) C25 0.0162(16) 0.0179(17) 0.0257(18) -0.0108(14) 0.0001(14) -0.0071(13) C47 0.0120(15) 0.0142(16) 0.0314(19) -0.0070(14) 0.0042(13) 0.0001(12) C12 0.0150(16) 0.0103(15) 0.034(2) -0.0038(14) 0.0035(14) 0.0005(13) C8 0.0164(17) 0.0189(17) 0.0234(18) -0.0069(14) 0.0011(14) -0.0082(13) N2 0.0119(13) 0.0184(14) 0.0350(17) -0.0051(12) 0.0043(12) -0.0031(11) N3 0.0135(13) 0.0162(14) 0.0324(16) -0.0070(12) 0.0055(12) -0.0048(11) O2S 0.0372(16) 0.0412(16) 0.0287(16) -0.0042(12) -0.0049(12) -0.0138(13) N1 0.0153(14) 0.0147(14) 0.0340(17) -0.0037(12) 0.0058(12) -0.0047(11) O1S 0.0246(14) 0.0446(16) 0.0285(14) -0.0098(12) -0.0007(11) -0.0037(12) N4 0.0136(14) 0.0173(14) 0.0292(16) -0.0032(12) 0.0033(12) -0.0037(11) O4S 0.0263(14) 0.0313(14) 0.0390(15) -0.0091(12) 0.0042(11) -0.0144(11) O2 0.0192(12) 0.0173(13) 0.0427(15) -0.0037(11) 0.0065(11) -0.0052(10) O3 0.0205(13) 0.0216(13) 0.0356(14) -0.0115(11) 0.0098(11) -0.0049(10) O4 0.0177(12) 0.0159(12) 0.0376(15) -0.0035(10) 0.0030(10) -0.0028(10) O3S 0.0216(13) 0.0265(13) 0.0357(15) -0.0082(11) 0.0028(11) -0.0075(10) O1 0.0170(12) 0.0187(12) 0.0382(15) -0.0064(10) 0.0079(10) -0.0045(10) _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 C9S Cl1X 1.519(10) . ? C9S Cl3 1.725(5) . ? C9S Cl2X 1.71(3) . ? C9S Cl3X 1.77(3) . ? C9S Cl2 1.770(5) . ? C9S Cl1 1.780(5) . ? C9S H1S 1.01(5) . ? C32 C30 1.517(5) . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C5S C6S 1.490(5) . ? C5S H5SA 0.9800 . ? C5S H5SB 0.9800 . ? C5S H5SC 0.9800 . ? C33 C30 1.524(5) . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C31 C30 1.533(5) . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C1S C2S 1.511(5) . ? C1S H1SA 0.9800 . ? C1S H1SB 0.9800 . ? C1S H1SC 0.9800 . ? C1 C200 1.536(5) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C3S C4S 1.485(5) . ? C3S H3SA 0.9800 . ? C3S H3SB 0.9800 . ? C3S H3SC 0.9800 . ? C2 C200 1.534(5) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C20 C19 1.357(5) . ? C20 C21 1.414(5) . ? C20 H20A 0.9500 . ? C7S O1S 1.447(4) . ? C7S C8S 1.494(6) . ? C7S H7SA 0.9900 . ? C7S H7SB 0.9900 . ? C3 C200 1.537(5) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C21 C22 1.357(5) . ? C21 H21A 0.9500 . ? C41 C40 1.354(5) . ? C41 C42 1.423(5) . ? C41 H41A 0.9500 . ? C2S O3S 1.454(4) . ? C2S H2SA 0.9900 . ? C2S H2SB 0.9900 . ? C6S O2S 1.207(4) . ? C6S O1S 1.342(4) . ? C4S O4S 1.219(4) . ? C4S O3S 1.326(4) . ? C8S H8SA 0.9800 . ? C8S H8SB 0.9800 . ? C8S H8SC 0.9800 . ? C200 C4 1.537(4) . ? C42 C43 1.356(5) . ? C42 H42A 0.9500 . ? C13 C11 1.355(5) . ? C13 C14 1.423(5) . ? C13 H13A 0.9500 . ? C43 C44 1.431(5) . ? C43 H43A 0.9500 . ? C22 C23 1.431(5) . ? C22 H22A 0.9500 . ? C19 C18 1.426(5) . ? C19 H19A 0.9500 . ? C14 C15 1.354(5) . ? C14 H14A 0.9500 . ? C9 N1 1.457(4) . ? C9 C12 1.512(4) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C49 C48 1.363(5) . ? C49 C50 1.407(5) . ? C49 H49A 0.9500 . ? C50 C51 1.354(5) . ? C50 H50A 0.9500 . ? C52 N2 1.464(4) . ? C52 C45 1.516(4) . ? C52 H52A 0.9900 . ? C52 H52B 0.9900 . ? C11 C10 1.431(5) . ? C11 H11A 0.9500 . ? C30 C28 1.544(4) . ? C40 C39 1.432(5) . ? C40 H40A 0.9500 . ? C27 C28 1.396(5) . ? C27 C26 1.397(4) . ? C27 H27A 0.9500 . ? C100 N3 1.461(4) . ? C100 C38 1.514(4) . ? C100 H10A 0.9900 . ? C100 H10B 0.9900 . ? C24 N4 1.464(4) . ? C24 C17 1.510(4) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C48 C47 1.432(5) . ? C48 H48A 0.9500 . ? C51 C46 1.434(5) . ? C51 H51A 0.9500 . ? C15 C16 1.435(5) . ? C15 H15A 0.9500 . ? C4 C55 1.392(4) . ? C4 C5 1.393(5) . ? C23 C12 1.406(5) . ? C23 C18 1.443(4) . ? C44 C45 1.405(5) . ? C44 C39 1.440(4) . ? C35 C29 1.393(4) . ? C35 C34 1.393(4) . ? C35 C36 1.492(4) . ? C7 C54 1.386(4) . ? C7 C6 1.395(4) . ? C7 H7A 0.9500 . ? C34 C28 1.393(4) . ? C34 H34A 0.9500 . ? C55 C54 1.399(4) . ? C55 H55A 0.9500 . ? C26 C29 1.384(4) . ? C26 C25 1.501(4) . ? C5 C6 1.398(4) . ? C5 H5A 0.9500 . ? C6 C8 1.491(4) . ? C53 O2 1.223(4) . ? C53 N2 1.341(4) . ? C53 C54 1.505(4) . ? C36 O3 1.232(4) . ? C36 N3 1.358(4) . ? C38 C47 1.401(5) . ? C38 C39 1.406(5) . ? C16 C17 1.405(5) . ? C16 C10 1.444(4) . ? C17 C18 1.410(5) . ? C29 H29A 0.9500 . ? C45 C46 1.403(5) . ? C46 C47 1.446(4) . ? C10 C12 1.406(5) . ? C25 O4 1.229(4) . ? C25 N4 1.344(4) . ? C8 O1 1.237(4) . ? C8 N1 1.352(4) . ? N2 H2D 0.8800 . ? N3 H3D 0.8800 . ? N1 H1D 0.8800 . ? N4 H4A 0.8800 . ? 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 Cl1X C9S Cl3 154.4(6) . . ? Cl1X C9S Cl2X 106.8(11) . . ? Cl3 C9S Cl2X 53.9(10) . . ? Cl1X C9S Cl3X 118.2(11) . . ? Cl3 C9S Cl3X 62.8(10) . . ? Cl2X C9S Cl3X 108.5(14) . . ? Cl1X C9S Cl2 72.2(5) . . ? Cl3 C9S Cl2 110.4(3) . . ? Cl2X C9S Cl2 139.3(10) . . ? Cl3X C9S Cl2 48.2(10) . . ? Cl1X C9S Cl1 49.0(5) . . ? Cl3 C9S Cl1 110.2(3) . . ? Cl2X C9S Cl1 57.8(10) . . ? Cl3X C9S Cl1 134.6(10) . . ? Cl2 C9S Cl1 110.9(3) . . ? Cl1X C9S H1S 96(3) . . ? Cl3 C9S H1S 106(3) . . ? Cl2X C9S H1S 109(3) . . ? Cl3X C9S H1S 117(3) . . ? Cl2 C9S H1S 111(3) . . ? Cl1 C9S H1S 108(3) . . ? C30 C32 H32A 109.5 . . ? C30 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C30 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C6S C5S H5SA 109.5 . . ? C6S C5S H5SB 109.5 . . ? H5SA C5S H5SB 109.5 . . ? C6S C5S H5SC 109.5 . . ? H5SA C5S H5SC 109.5 . . ? H5SB C5S H5SC 109.5 . . ? C30 C33 H33A 109.5 . . ? C30 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C30 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C2S C1S H1SA 109.5 . . ? C2S C1S H1SB 109.5 . . ? H1SA C1S H1SB 109.5 . . ? C2S C1S H1SC 109.5 . . ? H1SA C1S H1SC 109.5 . . ? H1SB C1S H1SC 109.5 . . ? C200 C1 H1A 109.5 . . ? C200 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C200 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C4S C3S H3SA 109.5 . . ? C4S C3S H3SB 109.5 . . ? H3SA C3S H3SB 109.5 . . ? C4S C3S H3SC 109.5 . . ? H3SA C3S H3SC 109.5 . . ? H3SB C3S H3SC 109.5 . . ? C200 C2 H2A 109.5 . . ? C200 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C200 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C19 C20 C21 120.2(4) . . ? C19 C20 H20A 119.9 . . ? C21 C20 H20A 119.9 . . ? O1S C7S C8S 110.9(3) . . ? O1S C7S H7SA 109.5 . . ? C8S C7S H7SA 109.5 . . ? O1S C7S H7SB 109.5 . . ? C8S C7S H7SB 109.5 . . ? H7SA C7S H7SB 108.0 . . ? C200 C3 H3A 109.5 . . ? C200 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C200 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C22 C21 C20 120.3(3) . . ? C22 C21 H21A 119.9 . . ? C20 C21 H21A 119.9 . . ? C40 C41 C42 120.2(3) . . ? C40 C41 H41A 119.9 . . ? C42 C41 H41A 119.9 . . ? O3S C2S C1S 106.8(3) . . ? O3S C2S H2SA 110.4 . . ? C1S C2S H2SA 110.4 . . ? O3S C2S H2SB 110.4 . . ? C1S C2S H2SB 110.4 . . ? H2SA C2S H2SB 108.6 . . ? O2S C6S O1S 123.3(3) . . ? O2S C6S C5S 125.7(3) . . ? O1S C6S C5S 111.0(3) . . ? O4S C4S O3S 123.3(3) . . ? O4S C4S C3S 124.7(3) . . ? O3S C4S C3S 112.0(3) . . ? C7S C8S H8SA 109.5 . . ? C7S C8S H8SB 109.5 . . ? H8SA C8S H8SB 109.5 . . ? C7S C8S H8SC 109.5 . . ? H8SA C8S H8SC 109.5 . . ? H8SB C8S H8SC 109.5 . . ? C2 C200 C1 108.7(3) . . ? C2 C200 C4 109.1(3) . . ? C1 C200 C4 112.2(3) . . ? C2 C200 C3 109.5(3) . . ? C1 C200 C3 108.4(3) . . ? C4 C200 C3 109.0(3) . . ? C43 C42 C41 120.3(3) . . ? C43 C42 H42A 119.9 . . ? C41 C42 H42A 119.9 . . ? C11 C13 C14 120.5(3) . . ? C11 C13 H13A 119.8 . . ? C14 C13 H13A 119.8 . . ? C42 C43 C44 121.7(3) . . ? C42 C43 H43A 119.1 . . ? C44 C43 H43A 119.1 . . ? C21 C22 C23 121.7(3) . . ? C21 C22 H22A 119.2 . . ? C23 C22 H22A 119.2 . . ? C20 C19 C18 122.1(3) . . ? C20 C19 H19A 119.0 . . ? C18 C19 H19A 119.0 . . ? C15 C14 C13 120.1(3) . . ? C15 C14 H14A 120.0 . . ? C13 C14 H14A 120.0 . . ? N1 C9 C12 113.2(3) . . ? N1 C9 H9A 108.9 . . ? C12 C9 H9A 108.9 . . ? N1 C9 H9B 108.9 . . ? C12 C9 H9B 108.9 . . ? H9A C9 H9B 107.7 . . ? C48 C49 C50 120.3(3) . . ? C48 C49 H49A 119.8 . . ? C50 C49 H49A 119.8 . . ? C51 C50 C49 120.6(3) . . ? C51 C50 H50A 119.7 . . ? C49 C50 H50A 119.7 . . ? N2 C52 C45 111.5(3) . . ? N2 C52 H52A 109.3 . . ? C45 C52 H52A 109.3 . . ? N2 C52 H52B 109.3 . . ? C45 C52 H52B 109.3 . . ? H52A C52 H52B 108.0 . . ? C13 C11 C10 121.6(3) . . ? C13 C11 H11A 119.2 . . ? C10 C11 H11A 119.2 . . ? C32 C30 C33 108.5(3) . . ? C32 C30 C31 109.4(3) . . ? C33 C30 C31 108.9(3) . . ? C32 C30 C28 112.1(3) . . ? C33 C30 C28 109.6(3) . . ? C31 C30 C28 108.3(3) . . ? C41 C40 C39 121.6(3) . . ? C41 C40 H40A 119.2 . . ? C39 C40 H40A 119.2 . . ? C28 C27 C26 121.2(3) . . ? C28 C27 H27A 119.4 . . ? C26 C27 H27A 119.4 . . ? N3 C100 C38 113.0(3) . . ? N3 C100 H10A 109.0 . . ? C38 C100 H10A 109.0 . . ? N3 C100 H10B 109.0 . . ? C38 C100 H10B 109.0 . . ? H10A C100 H10B 107.8 . . ? N4 C24 C17 112.6(3) . . ? N4 C24 H24A 109.1 . . ? C17 C24 H24A 109.1 . . ? N4 C24 H24B 109.1 . . ? C17 C24 H24B 109.1 . . ? H24A C24 H24B 107.8 . . ? C49 C48 C47 121.5(3) . . ? C49 C48 H48A 119.3 . . ? C47 C48 H48A 119.3 . . ? C50 C51 C46 121.9(3) . . ? C50 C51 H51A 119.0 . . ? C46 C51 H51A 119.0 . . ? C14 C15 C16 121.9(3) . . ? C14 C15 H15A 119.1 . . ? C16 C15 H15A 119.1 . . ? C55 C4 C5 117.9(3) . . ? C55 C4 C200 122.9(3) . . ? C5 C4 C200 119.2(3) . . ? C12 C23 C22 122.1(3) . . ? C12 C23 C18 119.8(3) . . ? C22 C23 C18 118.1(3) . . ? C45 C44 C43 122.3(3) . . ? C45 C44 C39 119.8(3) . . ? C43 C44 C39 117.9(3) . . ? C29 C35 C34 119.5(3) . . ? C29 C35 C36 123.1(3) . . ? C34 C35 C36 117.3(3) . . ? C54 C7 C6 119.8(3) . . ? C54 C7 H7A 120.1 . . ? C6 C7 H7A 120.1 . . ? C28 C34 C35 121.9(3) . . ? C28 C34 H34A 119.0 . . ? C35 C34 H34A 119.0 . . ? C4 C55 C54 121.2(3) . . ? C4 C55 H55A 119.4 . . ? C54 C55 H55A 119.4 . . ? C29 C26 C27 120.2(3) . . ? C29 C26 C25 121.6(3) . . ? C27 C26 C25 118.1(3) . . ? C4 C5 C6 121.8(3) . . ? C4 C5 H5A 119.1 . . ? C6 C5 H5A 119.1 . . ? C7 C6 C5 119.3(3) . . ? C7 C6 C8 123.0(3) . . ? C5 C6 C8 117.6(3) . . ? O2 C53 N2 122.0(3) . . ? O2 C53 C54 121.5(3) . . ? N2 C53 C54 116.5(3) . . ? O3 C36 N3 121.2(3) . . ? O3 C36 C35 121.8(3) . . ? N3 C36 C35 117.0(3) . . ? C34 C28 C27 117.5(3) . . ? C34 C28 C30 119.7(3) . . ? C27 C28 C30 122.8(3) . . ? C7 C54 C55 120.1(3) . . ? C7 C54 C53 122.3(3) . . ? C55 C54 C53 117.6(3) . . ? C47 C38 C39 120.4(3) . . ? C47 C38 C100 120.1(3) . . ? C39 C38 C100 119.4(3) . . ? C17 C16 C15 121.8(3) . . ? C17 C16 C10 120.3(3) . . ? C15 C16 C10 117.8(3) . . ? C38 C39 C40 122.2(3) . . ? C38 C39 C44 119.5(3) . . ? C40 C39 C44 118.3(3) . . ? C16 C17 C18 120.2(3) . . ? C16 C17 C24 119.4(3) . . ? C18 C17 C24 120.3(3) . . ? C26 C29 C35 119.6(3) . . ? C26 C29 H29A 120.2 . . ? C35 C29 H29A 120.2 . . ? C46 C45 C44 120.4(3) . . ? C46 C45 C52 120.4(3) . . ? C44 C45 C52 119.1(3) . . ? C45 C46 C51 123.1(3) . . ? C45 C46 C47 119.5(3) . . ? C51 C46 C47 117.5(3) . . ? C17 C18 C19 122.7(3) . . ? C17 C18 C23 119.5(3) . . ? C19 C18 C23 117.8(3) . . ? C12 C10 C11 122.8(3) . . ? C12 C10 C16 119.1(3) . . ? C11 C10 C16 118.1(3) . . ? O4 C25 N4 122.7(3) . . ? O4 C25 C26 121.4(3) . . ? N4 C25 C26 115.9(3) . . ? C38 C47 C48 122.0(3) . . ? C38 C47 C46 119.7(3) . . ? C48 C47 C46 118.2(3) . . ? C10 C12 C23 120.7(3) . . ? C10 C12 C9 120.2(3) . . ? C23 C12 C9 119.0(3) . . ? O1 C8 N1 121.2(3) . . ? O1 C8 C6 121.3(3) . . ? N1 C8 C6 117.5(3) . . ? C53 N2 C52 121.2(3) . . ? C53 N2 H2D 119.4 . . ? C52 N2 H2D 119.4 . . ? C36 N3 C100 120.3(3) . . ? C36 N3 H3D 119.8 . . ? C100 N3 H3D 119.8 . . ? C8 N1 C9 120.9(3) . . ? C8 N1 H1D 119.6 . . ? C9 N1 H1D 119.6 . . ? C6S O1S C7S 117.9(3) . . ? C25 N4 C24 121.4(3) . . ? C25 N4 H4A 119.3 . . ? C24 N4 H4A 119.3 . . ? C4S O3S C2S 117.6(3) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.814 _refine_diff_density_min -0.533 _refine_diff_density_rms 0.071 _chemical_compound_source synthesized _exptl_crystal_recrystallization_method 'Sample was dissolved in 1:1 CDCl3:EtOAc w slow evap' _vrf_PLAT221_new1 ; PROBLEM: Large Solvent/Anion Cl Ueq(max)/Ueq(min) ... 7.91 Ratio RESPONSE: Disodered solvent molcule that would not solve split. Atom is part of solvent modled as two chloroforms w/ site occupancy of ~ .33 and .66. Set ISOR=0.003. ;