# 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 'Vincent Lynch' _publ_contact_author_email vmlynch@mail.utexas.edu loop_ _publ_author_name 'Kwan-Bok Jung' 'Sung Kuk Kim' V.Lynch 'Dong-Gyu Cho' J.Sessler data_9 _database_code_depnum_ccdc_archive 'CCDC 858002' #TrackingRef '- combo-ChemComm 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2 C32 H32 N2 O2, C2 H3 N' _chemical_formula_sum 'C66 H67 N5 O4' _chemical_formula_weight 994.25 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pna21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 24.3554(10) _cell_length_b 11.3368(3) _cell_length_c 20.2929(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5603.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 7075 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.179 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2120 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.961 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details ; DENZO and Scalepack (Otwinoski and Minor, 1997) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12374 _diffrn_reflns_av_R_equivalents 0.0527 _diffrn_reflns_av_sigmaI/netI 0.0610 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.35 _diffrn_reflns_theta_max 27.48 _reflns_number_total 6597 _reflns_number_gt 4256 _reflns_threshold_expression >2sigma(I) _publ_section_references ; Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. Sir97. (1999) J. Appl. Cryst. 32, 115-119. Farrugia, L. J. (1999) J. Appl. Cryst., 32, 837-838. An Integrated System of Windows Programs for the Solution, Refinement and Analysis of Single Crystal X-ray Diffraction Data. Otwinowski, Z. and Minor, W. (1997). Methods in Enzymology, 276, Macromolecular Crystallography, part A, 307-326, C. W. Carter, Jr. and R. M. Sweets, Eds., Academic Press. Sheldrick, G. M. (2008). SHELXL-97. Acat Cryst., A64, 112-122. Spek, A. L. (1998) PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands. ; _computing_data_collection 'Collect software, Nonius B.V. 1998' _computing_cell_refinement 'Collect software, Nonius B.V. 1998' _computing_data_reduction ; DENZO and Scalepack (Otwinoski and Minor, 1997) ; _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _computing_publication_material ? _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. There are two crystallographically unique macrocycles in the asymmetric unit. One is H-bound to a molecule of acetonitrile. The second macrocycle is disordered by an approximately 180 degree rotation about the mean plane through the two orientations of the molecule. The disorder was modeled by restraining the geometry of the two components of the molecule to be equivalent. The site occupancy factor for one component was assigned the variable x, while the site occupancy factor for the second component was set to (1-x). A common isotropic displacement parameter was refined for atoms of both components while refining x. In this way, the site occupancy factor for the major component consisting of atoms with labels appended with an A refined to 79(2)%. The atoms of the major component were refined anisotropically with their displacement parameters restrained to be approximately isotropic. The hydrogen atoms for this molecule were calculated in idealized positions. The atoms of the minor component were refined isotropically. No hydrogen atoms for this molecule were included in the refinement. ; _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^)+(0.0777P)^2^+0.1980P] 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 SHELXL _refine_ls_extinction_coef 0.0019(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -3.0(17) _refine_ls_number_reflns 6597 _refine_ls_number_parameters 849 _refine_ls_number_restraints 1872 _refine_ls_R_factor_all 0.0972 _refine_ls_R_factor_gt 0.0519 _refine_ls_wR_factor_ref 0.1394 _refine_ls_wR_factor_gt 0.1218 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.130 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 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 O1 O 0.61999(10) 0.5078(2) 0.52804(13) 0.0342(6) Uani 1 1 d D . . O2 O 0.62482(10) 0.5084(2) 0.68525(12) 0.0338(6) Uani 1 1 d D . . N1 N 0.65804(11) 0.3699(2) 0.60554(15) 0.0283(6) Uani 1 1 d D . . H1N H 0.6899(16) 0.399(3) 0.602(3) 0.050(11) Uiso 1 1 d . . . N2 N 0.64991(10) 0.7326(2) 0.60082(16) 0.0320(6) Uani 1 1 d D . . H2N H 0.6320 0.6652 0.6020 0.038 Uiso 1 1 calc R . . C1 C 0.63041(14) 0.3819(3) 0.66627(16) 0.0345(9) Uani 1 1 d D . . C2 C 0.57339(16) 0.3358(4) 0.6521(2) 0.0528(12) Uani 1 1 d D . . H2A H 0.5454 0.3819 0.6764 0.063 Uiso 1 1 calc R . . H2B H 0.5702 0.2518 0.6650 0.063 Uiso 1 1 calc R . . C3 C 0.56624(15) 0.3502(4) 0.5785(2) 0.0514(12) Uani 1 1 d D . . H3A H 0.5394 0.4134 0.5689 0.062 Uiso 1 1 calc R . . H3B H 0.5529 0.2758 0.5586 0.062 Uiso 1 1 calc R . . C4 C 0.62305(15) 0.3827(3) 0.55050(17) 0.0347(9) Uani 1 1 d D . . C5 C 0.64485(16) 0.3184(3) 0.48823(18) 0.0444(10) Uani 1 1 d D . . C6 C 0.68023(16) 0.4157(3) 0.45940(18) 0.0402(10) Uani 1 1 d D . . C7 C 0.72284(19) 0.4129(4) 0.4152(2) 0.0509(12) Uani 1 1 d D . . H7A H 0.7369 0.3398 0.3997 0.061 Uiso 1 1 calc R . . C8 C 0.74504(18) 0.5183(3) 0.3936(2) 0.0497(11) Uani 1 1 d D . . H8A H 0.7760 0.5178 0.3651 0.060 Uiso 1 1 calc R . . C9 C 0.72227(17) 0.6248(4) 0.4136(2) 0.0448(10) Uani 1 1 d D . . H9A H 0.7372 0.6959 0.3965 0.054 Uiso 1 1 calc R . . C10 C 0.67834(15) 0.6316(3) 0.45768(18) 0.0325(9) Uani 1 1 d D . . C11 C 0.66053(14) 0.5228(3) 0.48113(17) 0.0309(9) Uani 1 1 d D . . C12 C 0.65033(14) 0.7484(3) 0.47547(17) 0.0361(9) Uani 1 1 d D . . C13 C 0.66576(14) 0.7900(3) 0.54388(16) 0.0303(9) Uani 1 1 d D . . C14 C 0.69345(15) 0.8890(3) 0.5634(2) 0.0368(10) Uani 1 1 d D . . H14A H 0.7100 0.9453 0.5350 0.044 Uiso 1 1 calc R . . C15 C 0.69340(15) 0.8935(3) 0.6328(2) 0.0392(10) Uani 1 1 d D . . H15A H 0.7095 0.9537 0.6591 0.047 Uiso 1 1 calc R . . C16 C 0.66611(15) 0.7959(3) 0.65587(17) 0.0337(9) Uani 1 1 d D . . C17 C 0.65179(14) 0.7586(3) 0.72528(17) 0.0351(9) Uani 1 1 d D . . C18 C 0.68320(14) 0.6474(3) 0.74599(18) 0.0353(9) Uani 1 1 d D . . C19 C 0.73034(16) 0.6511(4) 0.7856(2) 0.0499(11) Uani 1 1 d D . . H19A H 0.7437 0.7262 0.7989 0.060 Uiso 1 1 calc R . . C20 C 0.7586(2) 0.5521(4) 0.8066(2) 0.0624(14) Uani 1 1 d D . . H20A H 0.7903 0.5601 0.8334 0.075 Uiso 1 1 calc R . . C21 C 0.7404(2) 0.4415(4) 0.7882(2) 0.0617(14) Uani 1 1 d D . . H21A H 0.7593 0.3727 0.8022 0.074 Uiso 1 1 calc R . . C22 C 0.69389(16) 0.4327(3) 0.74889(18) 0.0416(10) Uani 1 1 d D . . C23 C 0.66816(14) 0.5339(3) 0.72751(18) 0.0329(9) Uani 1 1 d D . . C24 C 0.66313(18) 0.3261(3) 0.72450(18) 0.0496(11) Uani 1 1 d D . . C25 C 0.6754(2) 0.2053(4) 0.5058(2) 0.0600(13) Uani 1 1 d D . . H25A H 0.7084 0.2248 0.5312 0.090 Uiso 1 1 calc R . . H25B H 0.6859 0.1639 0.4654 0.090 Uiso 1 1 calc R . . H25C H 0.6515 0.1544 0.5323 0.090 Uiso 1 1 calc R . . C26 C 0.5968(2) 0.2908(4) 0.4406(2) 0.0611(13) Uani 1 1 d D . . H26A H 0.6115 0.2636 0.3983 0.092 Uiso 1 1 calc R . . H26B H 0.5749 0.3622 0.4337 0.092 Uiso 1 1 calc R . . H26C H 0.5736 0.2290 0.4597 0.092 Uiso 1 1 calc R . . C27 C 0.58750(14) 0.7336(4) 0.4704(2) 0.0380(9) Uani 1 1 d D . . H27A H 0.5777 0.7114 0.4252 0.057 Uiso 1 1 calc R . . H27B H 0.5695 0.8081 0.4818 0.057 Uiso 1 1 calc R . . H27C H 0.5754 0.6717 0.5008 0.057 Uiso 1 1 calc R . . C28 C 0.6658(2) 0.8459(4) 0.4260(2) 0.0519(12) Uani 1 1 d D . . H28A H 0.6565 0.8201 0.3813 0.078 Uiso 1 1 calc R . . H28B H 0.7053 0.8615 0.4287 0.078 Uiso 1 1 calc R . . H28C H 0.6455 0.9181 0.4365 0.078 Uiso 1 1 calc R . . C29 C 0.58953(15) 0.7378(4) 0.7318(2) 0.0406(10) Uani 1 1 d D . . H29A H 0.5701 0.8131 0.7272 0.061 Uiso 1 1 calc R . . H29B H 0.5815 0.7036 0.7751 0.061 Uiso 1 1 calc R . . H29C H 0.5773 0.6835 0.6972 0.061 Uiso 1 1 calc R . . C30 C 0.66650(19) 0.8617(4) 0.7715(2) 0.0512(12) Uani 1 1 d D . . H30A H 0.7052 0.8829 0.7655 0.077 Uiso 1 1 calc R . . H30B H 0.6603 0.8380 0.8173 0.077 Uiso 1 1 calc R . . H30C H 0.6433 0.9299 0.7611 0.077 Uiso 1 1 calc R . . C31 C 0.7002(3) 0.2238(4) 0.7028(2) 0.085(2) Uani 1 1 d D . . H31A H 0.7282 0.2533 0.6724 0.127 Uiso 1 1 calc R . . H31B H 0.6780 0.1636 0.6807 0.127 Uiso 1 1 calc R . . H31C H 0.7180 0.1892 0.7416 0.127 Uiso 1 1 calc R . . C32 C 0.6257(3) 0.2845(5) 0.7798(2) 0.0795(18) Uani 1 1 d D . . H32A H 0.6476 0.2686 0.8193 0.119 Uiso 1 1 calc R . . H32B H 0.6067 0.2123 0.7662 0.119 Uiso 1 1 calc R . . H32C H 0.5985 0.3460 0.7895 0.119 Uiso 1 1 calc R . . N1B N 0.77001(13) 0.4888(3) 0.6011(3) 0.0650(10) Uani 1 1 d . . . C1B C 0.78664(14) 0.5819(4) 0.6049(3) 0.0474(9) Uani 1 1 d . . . C2B C 0.80894(19) 0.6988(4) 0.6120(4) 0.0779(17) Uani 1 1 d . . . H2B1 H 0.8157 0.7150 0.6588 0.117 Uiso 1 1 calc R . . H2B2 H 0.7827 0.7565 0.5946 0.117 Uiso 1 1 calc R . . H2B3 H 0.8435 0.7044 0.5875 0.117 Uiso 1 1 calc R . . O1A O 0.36831(12) 0.4344(3) 0.57979(15) 0.0335(7) Uani 0.79 1 d PDU A 1 O2A O 0.40184(12) 0.1624(3) 0.58509(16) 0.0337(7) Uani 0.79 1 d PDU A 1 N1A N 0.4194(2) 0.3146(4) 0.5041(3) 0.0297(11) Uani 0.79 1 d PDU A 1 N2A N 0.4176(2) 0.3065(4) 0.7075(4) 0.0334(12) Uani 0.79 1 d PDU A 1 H2A1 H 0.3987 0.2946 0.6712 0.040 Uiso 0.79 1 calc PR A 1 C1A C 0.39725(17) 0.1996(4) 0.5146(2) 0.0347(10) Uani 0.79 1 d PDU A 1 C2A C 0.33627(18) 0.2124(4) 0.4993(3) 0.0423(12) Uani 0.79 1 d PDU A 1 H2A2 H 0.3139 0.1884 0.5378 0.051 Uiso 0.79 1 calc PR A 1 H2A3 H 0.3260 0.1628 0.4611 0.051 Uiso 0.79 1 calc PR A 1 C3A C 0.32736(19) 0.3426(4) 0.4837(3) 0.0403(12) Uani 0.79 1 d PDU A 1 H3A1 H 0.3237 0.3550 0.4356 0.048 Uiso 0.79 1 calc PR A 1 H3A2 H 0.2939 0.3726 0.5058 0.048 Uiso 0.79 1 calc PR A 1 C4A C 0.37842(17) 0.4041(4) 0.5101(2) 0.0330(10) Uani 0.79 1 d PDU A 1 C5A C 0.39574(19) 0.5239(4) 0.4787(3) 0.0358(13) Uani 0.79 1 d PDU A 1 C6A C 0.4204(2) 0.5843(5) 0.5380(3) 0.0360(15) Uani 0.79 1 d PDU A 1 C7A C 0.4545(2) 0.6810(6) 0.5437(3) 0.0423(15) Uani 0.79 1 d PDU A 1 H7A1 H 0.4687 0.7177 0.5053 0.051 Uiso 0.79 1 calc PR A 1 C8A C 0.4680(3) 0.7246(6) 0.6055(3) 0.0442(14) Uani 0.79 1 d PDU A 1 H8A1 H 0.4915 0.7913 0.6091 0.053 Uiso 0.79 1 calc PR A 1 C9A C 0.4476(3) 0.6717(6) 0.6623(4) 0.0444(15) Uani 0.79 1 d PDU A 1 H9A1 H 0.4575 0.7017 0.7043 0.053 Uiso 0.79 1 calc PR A 1 C10A C 0.4121(2) 0.5734(5) 0.6577(2) 0.0332(12) Uani 0.79 1 d PDU A 1 C11A C 0.4008(2) 0.5322(4) 0.5947(2) 0.0297(12) Uani 0.79 1 d PDU A 1 C12A C 0.38773(19) 0.5199(4) 0.7205(3) 0.0372(13) Uani 0.79 1 d PDU A 1 C13A C 0.42054(17) 0.4130(4) 0.7410(2) 0.0351(10) Uani 0.79 1 d PDU A 1 C14A C 0.45369(18) 0.3949(5) 0.7940(2) 0.0427(12) Uani 0.79 1 d PDU A 1 H14B H 0.4635 0.4521 0.8262 0.051 Uiso 0.79 1 calc PR A 1 C15A C 0.4712(2) 0.2744(4) 0.7929(2) 0.0414(12) Uani 0.79 1 d PDU A 1 H15B H 0.4947 0.2377 0.8242 0.050 Uiso 0.79 1 calc PR A 1 C16A C 0.44855(17) 0.2215(4) 0.7395(2) 0.0350(10) Uani 0.79 1 d PDU A 1 C17A C 0.44932(19) 0.0936(4) 0.7183(2) 0.0328(12) Uani 0.79 1 d PDU A 1 C18A C 0.47731(17) 0.0778(4) 0.6515(2) 0.0301(11) Uani 0.79 1 d PDU A 1 C19A C 0.52924(17) 0.0276(3) 0.6444(3) 0.0315(10) Uani 0.79 1 d PDU A 1 H19B H 0.5491 0.0091 0.6833 0.038 Uiso 0.79 1 calc PR A 1 C20A C 0.55391(19) 0.0029(4) 0.5840(3) 0.0360(11) Uani 0.79 1 d PDU A 1 H20B H 0.5897 -0.0302 0.5824 0.043 Uiso 0.79 1 calc PR A 1 C21A C 0.52558(19) 0.0271(4) 0.5259(3) 0.0369(11) Uani 0.79 1 d PDU A 1 H21B H 0.5413 0.0093 0.4843 0.044 Uiso 0.79 1 calc PR A 1 C22A C 0.47405(18) 0.0776(4) 0.5304(2) 0.0319(12) Uani 0.79 1 d PDU A 1 C23A C 0.45238(16) 0.1050(4) 0.5919(2) 0.0285(10) Uani 0.79 1 d PDU A 1 C24A C 0.43098(19) 0.1023(4) 0.4787(2) 0.0382(13) Uani 0.79 1 d PDU A 1 C25A C 0.3440(2) 0.5921(5) 0.4565(3) 0.0460(13) Uani 0.79 1 d PDU A 1 H25D H 0.3168 0.5915 0.4920 0.069 Uiso 0.79 1 calc PR A 1 H25E H 0.3285 0.5543 0.4172 0.069 Uiso 0.79 1 calc PR A 1 H25F H 0.3540 0.6737 0.4460 0.069 Uiso 0.79 1 calc PR A 1 C26A C 0.4351(2) 0.5087(5) 0.4203(3) 0.0511(14) Uani 0.79 1 d PDU A 1 H26D H 0.4443 0.5863 0.4021 0.077 Uiso 0.79 1 calc PR A 1 H26E H 0.4175 0.4605 0.3862 0.077 Uiso 0.79 1 calc PR A 1 H26F H 0.4688 0.4697 0.4353 0.077 Uiso 0.79 1 calc PR A 1 C27A C 0.3899(3) 0.6082(5) 0.7782(3) 0.0513(14) Uani 0.79 1 d PDU A 1 H27D H 0.3707 0.5748 0.8164 0.077 Uiso 0.79 1 calc PR A 1 H27E H 0.3720 0.6820 0.7651 0.077 Uiso 0.79 1 calc PR A 1 H27F H 0.4283 0.6239 0.7899 0.077 Uiso 0.79 1 calc PR A 1 C28A C 0.32677(17) 0.4877(5) 0.7117(3) 0.0425(12) Uani 0.79 1 d PDU A 1 H28D H 0.3232 0.4266 0.6778 0.064 Uiso 0.79 1 calc PR A 1 H28E H 0.3062 0.5579 0.6981 0.064 Uiso 0.79 1 calc PR A 1 H28F H 0.3121 0.4582 0.7535 0.064 Uiso 0.79 1 calc PR A 1 C29A C 0.3899(2) 0.0436(5) 0.7154(3) 0.0466(13) Uani 0.79 1 d PDU A 1 H29D H 0.3677 0.0917 0.6854 0.070 Uiso 0.79 1 calc PR A 1 H29E H 0.3736 0.0454 0.7595 0.070 Uiso 0.79 1 calc PR A 1 H29F H 0.3909 -0.0380 0.6993 0.070 Uiso 0.79 1 calc PR A 1 C30A C 0.4794(3) 0.0222(5) 0.7718(3) 0.0541(15) Uani 0.79 1 d PDU A 1 H30D H 0.4819 -0.0605 0.7582 0.081 Uiso 0.79 1 calc PR A 1 H30E H 0.4590 0.0275 0.8134 0.081 Uiso 0.79 1 calc PR A 1 H30F H 0.5164 0.0542 0.7780 0.081 Uiso 0.79 1 calc PR A 1 C31A C 0.3971(3) -0.0119(5) 0.4690(3) 0.0564(16) Uani 0.79 1 d PDU A 1 H31D H 0.4210 -0.0746 0.4523 0.085 Uiso 0.79 1 calc PR A 1 H31E H 0.3675 0.0028 0.4373 0.085 Uiso 0.79 1 calc PR A 1 H31F H 0.3813 -0.0361 0.5113 0.085 Uiso 0.79 1 calc PR A 1 C32A C 0.4532(2) 0.1433(5) 0.4119(2) 0.0496(14) Uani 0.79 1 d PDU A 1 H32D H 0.4773 0.2116 0.4184 0.074 Uiso 0.79 1 calc PR A 1 H32E H 0.4225 0.1656 0.3832 0.074 Uiso 0.79 1 calc PR A 1 H32F H 0.4740 0.0791 0.3914 0.074 Uiso 0.79 1 calc PR A 1 O1C O 0.4039(4) 0.1600(10) 0.6276(6) 0.027(2) Uiso 0.21 1 d PDU B 2 O2C O 0.3712(5) 0.4294(10) 0.6319(5) 0.032(2) Uiso 0.21 1 d PDU B 2 N1C N 0.4234(8) 0.3105(13) 0.7055(18) 0.032(3) Uiso 0.21 1 d PDU B 2 N2C N 0.4137(8) 0.2982(14) 0.5050(10) 0.034(3) Uiso 0.21 1 d PDU B 2 C1C C 0.3840(6) 0.4009(12) 0.6997(6) 0.033(3) Uiso 0.21 1 d PDU B 2 C2C C 0.3343(6) 0.3398(13) 0.7296(9) 0.039(4) Uiso 0.21 1 d PDU B 2 C3C C 0.3430(8) 0.2087(13) 0.7182(10) 0.042(4) Uiso 0.21 1 d PDU B 2 C4C C 0.4030(6) 0.1953(13) 0.6960(6) 0.030(3) Uiso 0.21 1 d PDU B 2 C5C C 0.4377(7) 0.1010(15) 0.7331(8) 0.036(3) Uiso 0.21 1 d PDU B 2 C6C C 0.4794(6) 0.0761(14) 0.6801(9) 0.030(3) Uiso 0.21 1 d PDU B 2 C7C C 0.5313(6) 0.0275(13) 0.6804(9) 0.034(3) Uiso 0.21 1 d PDU B 2 C8C C 0.5554(8) 0.0034(15) 0.6198(9) 0.034(3) Uiso 0.21 1 d PDU B 2 C9C C 0.5324(9) 0.0230(17) 0.5581(9) 0.031(3) Uiso 0.21 1 d PDU B 2 C10C C 0.4776(9) 0.0742(18) 0.5566(10) 0.029(3) Uiso 0.21 1 d PDU B 2 C11C C 0.4549(6) 0.0982(14) 0.6206(9) 0.027(3) Uiso 0.21 1 d PDU B 2 C12C C 0.4474(7) 0.0883(13) 0.4917(8) 0.033(3) Uiso 0.21 1 d PDU B 2 C13C C 0.4424(6) 0.2148(13) 0.4678(7) 0.034(3) Uiso 0.21 1 d PDU B 2 C14C C 0.4631(7) 0.2617(17) 0.4113(7) 0.044(4) Uiso 0.21 1 d PDU B 2 C15C C 0.4471(7) 0.3837(19) 0.4112(8) 0.047(4) Uiso 0.21 1 d PDU B 2 C16C C 0.4176(6) 0.4016(14) 0.4677(7) 0.033(3) Uiso 0.21 1 d PDU B 2 C17C C 0.3850(7) 0.5107(15) 0.4871(10) 0.037(3) Uiso 0.21 1 d PDU B 2 C18C C 0.4116(10) 0.570(3) 0.5465(13) 0.036(3) Uiso 0.21 1 d PDU B 2 C19C C 0.4439(10) 0.669(3) 0.5338(15) 0.044(3) Uiso 0.21 1 d PDU B 2 C20C C 0.4657(12) 0.726(3) 0.5883(13) 0.044(3) Uiso 0.21 1 d PDU B 2 C21C C 0.4542(11) 0.682(2) 0.6508(15) 0.041(3) Uiso 0.21 1 d PDU B 2 C22C C 0.4235(9) 0.587(2) 0.6719(10) 0.038(3) Uiso 0.21 1 d PDU B 2 C23C C 0.4027(8) 0.5326(15) 0.6167(12) 0.030(3) Uiso 0.21 1 d PDU B 2 C24C C 0.4000(7) 0.5218(15) 0.7305(9) 0.036(3) Uiso 0.21 1 d PDU B 2 C25C C 0.4649(8) 0.147(2) 0.7971(9) 0.051(4) Uiso 0.21 1 d PDU B 2 C26C C 0.4028(10) -0.011(2) 0.7445(14) 0.061(6) Uiso 0.21 1 d PDU B 2 C27C C 0.3884(7) 0.038(2) 0.4963(12) 0.048(5) Uiso 0.21 1 d PDU B 2 C28C C 0.4742(9) 0.0141(19) 0.4370(10) 0.056(5) Uiso 0.21 1 d PDU B 2 C29C C 0.3242(7) 0.4806(19) 0.4998(11) 0.047(4) Uiso 0.21 1 d PDU B 2 C30C C 0.3854(11) 0.604(2) 0.4319(11) 0.061(5) Uiso 0.21 1 d PDU B 2 C31C C 0.4427(8) 0.5149(19) 0.7862(10) 0.048(4) Uiso 0.21 1 d PDU B 2 C32C C 0.3508(9) 0.598(2) 0.7528(11) 0.054(4) Uiso 0.21 1 d PDU B 2 H1NA H 0.4494(17) 0.326(4) 0.524(2) 0.050(13) 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 O1 0.0381(14) 0.0261(15) 0.0382(15) 0.0043(11) -0.0002(12) 0.0003(11) O2 0.0347(14) 0.0263(14) 0.0405(15) -0.0084(12) -0.0007(12) 0.0024(11) N1 0.0297(14) 0.0265(13) 0.0287(14) -0.0009(16) -0.0015(16) -0.0009(11) N2 0.0357(13) 0.0237(13) 0.0367(16) -0.0013(16) 0.0040(17) -0.0041(10) C1 0.043(2) 0.027(2) 0.033(2) -0.0040(17) 0.0079(17) -0.0033(16) C2 0.045(2) 0.043(3) 0.070(3) -0.020(2) 0.019(2) -0.018(2) C3 0.036(2) 0.037(2) 0.081(3) 0.018(2) -0.017(2) -0.0108(17) C4 0.044(2) 0.021(2) 0.039(2) 0.0012(17) -0.0088(18) -0.0010(16) C5 0.073(3) 0.025(2) 0.034(2) -0.0007(17) -0.007(2) 0.0012(19) C6 0.063(3) 0.032(2) 0.025(2) -0.0038(17) -0.0055(19) 0.0077(19) C7 0.081(3) 0.040(3) 0.032(2) -0.006(2) 0.002(2) 0.022(2) C8 0.056(3) 0.058(3) 0.036(2) 0.000(2) 0.018(2) 0.019(2) C9 0.051(2) 0.046(2) 0.037(2) 0.0066(19) 0.012(2) 0.008(2) C10 0.037(2) 0.027(2) 0.033(2) 0.0020(16) 0.0064(17) 0.0043(16) C11 0.035(2) 0.032(2) 0.0258(19) 0.0006(16) -0.0008(16) 0.0074(16) C12 0.045(2) 0.026(2) 0.037(2) 0.0068(17) 0.0024(19) 0.0025(17) C13 0.0295(19) 0.020(2) 0.041(2) 0.0038(17) 0.0073(17) 0.0053(16) C14 0.032(2) 0.024(2) 0.054(3) 0.0019(18) 0.0067(18) 0.0000(17) C15 0.025(2) 0.029(2) 0.064(3) -0.0068(19) 0.0006(17) 0.0011(17) C16 0.033(2) 0.024(2) 0.044(2) -0.0060(18) 0.0016(19) 0.0003(16) C17 0.039(2) 0.028(2) 0.039(2) -0.0097(18) -0.0060(18) 0.0040(16) C18 0.037(2) 0.039(2) 0.030(2) -0.0087(17) -0.0017(17) -0.0002(17) C19 0.052(3) 0.059(3) 0.039(2) -0.012(2) -0.012(2) 0.006(2) C20 0.066(3) 0.078(4) 0.044(3) -0.017(3) -0.022(2) 0.020(3) C21 0.089(4) 0.064(3) 0.032(2) -0.002(2) -0.015(2) 0.030(3) C22 0.062(3) 0.037(2) 0.026(2) -0.0001(17) -0.0022(19) 0.0127(19) C23 0.035(2) 0.039(2) 0.0252(19) -0.0040(17) 0.0015(16) 0.0018(17) C24 0.092(3) 0.029(2) 0.028(2) 0.0037(19) 0.004(2) 0.002(2) C25 0.094(4) 0.035(2) 0.051(3) -0.008(2) 0.010(3) 0.015(2) C26 0.086(3) 0.056(3) 0.042(3) 0.000(2) -0.016(2) -0.022(3) C27 0.039(2) 0.034(2) 0.041(2) 0.0018(18) -0.0024(18) 0.0117(18) C28 0.068(3) 0.037(3) 0.050(3) 0.013(2) 0.016(2) 0.004(2) C29 0.046(2) 0.037(2) 0.038(2) -0.0054(19) 0.0067(19) 0.0063(19) C30 0.065(3) 0.042(3) 0.047(3) -0.023(2) -0.002(2) -0.005(2) C31 0.165(6) 0.040(3) 0.049(3) -0.009(2) -0.029(4) 0.051(3) C32 0.143(5) 0.056(3) 0.040(3) 0.003(2) 0.012(3) -0.035(3) N1B 0.0421(18) 0.063(2) 0.090(3) -0.013(3) 0.009(2) -0.0076(17) C1B 0.0279(17) 0.054(2) 0.060(2) 0.003(3) 0.005(2) 0.0033(16) C2B 0.057(3) 0.038(2) 0.138(5) 0.002(3) 0.009(4) 0.0028(19) O1A 0.0339(15) 0.0308(16) 0.0359(17) -0.0004(13) 0.0025(13) -0.0052(12) O2A 0.0299(14) 0.0376(17) 0.0337(18) 0.0052(13) -0.0038(13) 0.0053(12) N1A 0.026(2) 0.028(2) 0.035(2) 0.0031(19) -0.0041(18) 0.0010(18) N2A 0.034(2) 0.039(2) 0.027(2) -0.0024(18) -0.006(2) 0.0028(18) C1A 0.038(2) 0.033(2) 0.033(2) 0.0034(19) -0.0081(19) -0.0042(18) C2A 0.038(2) 0.044(3) 0.045(3) 0.007(2) -0.017(2) -0.002(2) C3A 0.037(2) 0.044(3) 0.040(3) 0.000(2) -0.010(2) -0.001(2) C4A 0.031(2) 0.035(2) 0.033(2) -0.0003(19) -0.0030(18) 0.0025(17) C5A 0.036(2) 0.035(2) 0.036(3) 0.007(2) 0.000(2) -0.001(2) C6A 0.031(3) 0.028(3) 0.048(3) 0.008(2) 0.000(2) 0.005(2) C7A 0.034(3) 0.036(3) 0.056(4) 0.001(3) -0.008(3) -0.002(2) C8A 0.042(2) 0.037(2) 0.053(4) 0.004(3) -0.007(3) -0.0125(17) C9A 0.045(3) 0.039(3) 0.049(3) 0.000(3) 0.005(3) -0.002(2) C10A 0.029(2) 0.032(2) 0.039(3) -0.003(2) -0.001(2) 0.001(2) C11A 0.0256(18) 0.0258(19) 0.038(3) -0.003(2) -0.001(2) 0.0018(14) C12A 0.039(3) 0.037(2) 0.036(3) -0.007(2) 0.002(2) 0.008(2) C13A 0.038(2) 0.037(2) 0.031(2) -0.0055(19) 0.0027(19) -0.0009(19) C14A 0.050(3) 0.048(3) 0.030(2) -0.003(2) -0.007(2) 0.006(2) C15A 0.045(3) 0.051(3) 0.028(2) 0.002(2) -0.006(2) 0.003(2) C16A 0.035(2) 0.041(2) 0.030(2) 0.0052(19) -0.0023(19) 0.0034(18) C17A 0.036(3) 0.030(2) 0.032(2) 0.010(2) -0.002(2) 0.0051(19) C18A 0.035(2) 0.025(2) 0.031(2) 0.003(2) -0.004(2) -0.0040(17) C19A 0.037(2) 0.022(2) 0.036(3) 0.0019(19) -0.006(2) 0.0006(18) C20A 0.039(2) 0.023(2) 0.046(3) 0.004(2) 0.000(2) 0.0024(18) C21A 0.042(2) 0.027(2) 0.042(3) 0.002(2) 0.007(2) 0.0004(19) C22A 0.036(2) 0.024(2) 0.035(3) -0.004(2) 0.000(2) -0.0014(18) C23A 0.0280(18) 0.0242(19) 0.033(3) 0.0032(19) -0.004(2) 0.0001(15) C24A 0.040(3) 0.040(3) 0.034(2) -0.009(2) -0.007(2) 0.003(2) C25A 0.047(3) 0.041(3) 0.049(3) 0.008(2) -0.007(2) 0.009(2) C26A 0.065(3) 0.044(3) 0.044(3) 0.013(2) 0.011(3) 0.007(2) C27A 0.063(3) 0.047(3) 0.044(3) -0.015(2) 0.002(3) 0.011(2) C28A 0.037(2) 0.053(3) 0.038(3) 0.002(2) 0.009(2) 0.008(2) C29A 0.051(3) 0.044(3) 0.045(3) 0.011(3) 0.008(2) -0.008(2) C30A 0.070(3) 0.048(3) 0.044(3) 0.018(2) -0.006(3) 0.016(3) C31A 0.064(3) 0.041(3) 0.065(4) -0.010(3) -0.026(3) -0.008(3) C32A 0.063(3) 0.054(3) 0.032(3) -0.006(2) 0.001(2) 0.007(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C11 1.382(4) . ? O1 C4 1.492(4) . ? O2 C23 1.390(4) . ? O2 C1 1.491(4) . ? N1 C1 1.411(4) . ? N1 C4 1.412(4) . ? N1 H1N 0.85(4) . ? N2 C13 1.381(4) . ? N2 C16 1.386(4) . ? N2 H2N 0.8800 . ? C1 C2 1.511(5) . ? C1 C24 1.559(5) . ? C2 C3 1.514(6) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.540(5) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.552(5) . ? C5 C6 1.517(5) . ? C5 C25 1.524(5) . ? C5 C26 1.550(5) . ? C6 C7 1.372(5) . ? C6 C11 1.379(4) . ? C7 C8 1.383(5) . ? C7 H7A 0.9500 . ? C8 C9 1.389(5) . ? C8 H8A 0.9500 . ? C9 C10 1.397(5) . ? C9 H9A 0.9500 . ? C10 C11 1.391(5) . ? C10 C12 1.533(4) . ? C12 C13 1.513(4) . ? C12 C28 1.540(5) . ? C12 C27 1.543(5) . ? C13 C14 1.368(4) . ? C14 C15 1.409(5) . ? C14 H14A 0.9500 . ? C15 C16 1.373(5) . ? C15 H15A 0.9500 . ? C16 C17 1.512(5) . ? C17 C18 1.534(4) . ? C17 C29 1.540(4) . ? C17 C30 1.541(4) . ? C18 C23 1.389(5) . ? C18 C19 1.402(5) . ? C19 C20 1.384(5) . ? C19 H19A 0.9500 . ? C20 C21 1.382(5) . ? C20 H20A 0.9500 . ? C21 C22 1.388(5) . ? C21 H21A 0.9500 . ? C22 C23 1.377(4) . ? C22 C24 1.506(5) . ? C24 C32 1.521(5) . ? C24 C31 1.534(5) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? N1B C1B 1.133(5) . ? C1B C2B 1.440(6) . ? C2B H2B1 0.9800 . ? C2B H2B2 0.9800 . ? C2B H2B3 0.9800 . ? O1A C11A 1.396(4) . ? O1A C4A 1.475(5) . ? O2A C23A 1.399(4) . ? O2A C1A 1.496(5) . ? N1A C1A 1.426(5) . ? N1A C4A 1.429(5) . ? N1A H1NA 0.84(4) . ? N2A C16A 1.385(6) . ? N2A C13A 1.387(6) . ? N2A H2A1 0.8800 . ? C1A C2A 1.524(6) . ? C1A C24A 1.557(6) . ? C2A C3A 1.526(6) . ? C2A H2A2 0.9900 . ? C2A H2A3 0.9900 . ? C3A C4A 1.523(6) . ? C3A H3A1 0.9900 . ? C3A H3A2 0.9900 . ? C4A C5A 1.558(6) . ? C5A C6A 1.507(6) . ? C5A C26A 1.535(6) . ? C5A C25A 1.546(6) . ? C6A C7A 1.380(6) . ? C6A C11A 1.379(6) . ? C7A C8A 1.388(6) . ? C7A H7A1 0.9500 . ? C8A C9A 1.391(6) . ? C8A H8A1 0.9500 . ? C9A C10A 1.413(7) . ? C9A H9A1 0.9500 . ? C10A C11A 1.388(6) . ? C10A C12A 1.532(5) . ? C12A C13A 1.510(5) . ? C12A C28A 1.539(5) . ? C12A C27A 1.542(5) . ? C13A C14A 1.362(5) . ? C14A C15A 1.431(6) . ? C14A H14B 0.9500 . ? C15A C16A 1.355(5) . ? C15A H15B 0.9500 . ? C16A C17A 1.513(5) . ? C17A C18A 1.527(5) . ? C17A C30A 1.541(5) . ? C17A C29A 1.556(5) . ? C18A C23A 1.389(6) . ? C18A C19A 1.394(5) . ? C19A C20A 1.394(6) . ? C19A H19B 0.9500 . ? C20A C21A 1.392(6) . ? C20A H20B 0.9500 . ? C21A C22A 1.383(5) . ? C21A H21B 0.9500 . ? C22A C23A 1.390(5) . ? C22A C24A 1.510(6) . ? C24A C32A 1.531(5) . ? C24A C31A 1.547(5) . ? C25A H25D 0.9800 . ? C25A H25E 0.9800 . ? C25A H25F 0.9800 . ? C26A H26D 0.9800 . ? C26A H26E 0.9800 . ? C26A H26F 0.9800 . ? C27A H27D 0.9800 . ? C27A H27E 0.9800 . ? C27A H27F 0.9800 . ? C28A H28D 0.9800 . ? C28A H28E 0.9800 . ? C28A H28F 0.9800 . ? C29A H29D 0.9800 . ? C29A H29E 0.9800 . ? C29A H29F 0.9800 . ? C30A H30D 0.9800 . ? C30A H30E 0.9800 . ? C30A H30F 0.9800 . ? C31A H31D 0.9800 . ? C31A H31E 0.9800 . ? C31A H31F 0.9800 . ? C32A H32D 0.9800 . ? C32A H32E 0.9800 . ? C32A H32F 0.9800 . ? O1C C11C 1.433(8) . ? O1C C4C 1.445(8) . ? O2C C23C 1.434(8) . ? O2C C1C 1.448(8) . ? N1C C1C 1.409(9) . ? N1C C4C 1.409(9) . ? N2C C13C 1.399(9) . ? N2C C16C 1.400(9) . ? N2C H1NA 1.00(5) . ? C1C C2C 1.520(10) . ? C1C C24C 1.556(9) . ? C2C C3C 1.519(10) . ? C3C C4C 1.54(2) . ? C4C C5C 1.558(9) . ? C5C C6C 1.505(9) . ? C5C C25C 1.545(8) . ? C5C C26C 1.546(8) . ? C6C C11C 1.370(8) . ? C6C C7C 1.381(8) . ? C7C C8C 1.389(8) . ? C8C C9C 1.390(8) . ? C9C C10C 1.46(3) . ? C10C C11C 1.44(3) . ? C10C C12C 1.517(8) . ? C12C C13C 1.518(8) . ? C12C C28C 1.538(8) . ? C12C C27C 1.547(8) . ? C13C C14C 1.361(9) . ? C14C C15C 1.44(3) . ? C15C C16C 1.368(9) . ? C16C C17C 1.522(9) . ? C17C C18C 1.526(9) . ? C17C C30C 1.542(8) . ? C17C C29C 1.542(8) . ? C18C C19C 1.390(9) . ? C18C C23C 1.50(3) . ? C19C C20C 1.388(9) . ? C20C C21C 1.390(8) . ? C21C C22C 1.381(9) . ? C22C C23C 1.376(9) . ? C22C C24C 1.512(9) . ? C24C C31C 1.538(8) . ? C24C C32C 1.542(8) . ? 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 C11 O1 C4 107.0(3) . . ? C23 O2 C1 106.8(2) . . ? C1 N1 C4 113.1(3) . . ? C1 N1 H1N 118(3) . . ? C4 N1 H1N 117(3) . . ? C13 N2 C16 110.5(2) . . ? C13 N2 H2N 124.7 . . ? C16 N2 H2N 124.7 . . ? N1 C1 O2 111.2(3) . . ? N1 C1 C2 103.8(3) . . ? O2 C1 C2 107.3(3) . . ? N1 C1 C24 112.3(3) . . ? O2 C1 C24 104.0(3) . . ? C2 C1 C24 118.2(3) . . ? C1 C2 C3 104.8(3) . . ? C1 C2 H2A 110.8 . . ? C3 C2 H2A 110.8 . . ? C1 C2 H2B 110.8 . . ? C3 C2 H2B 110.8 . . ? H2A C2 H2B 108.9 . . ? C2 C3 C4 106.6(3) . . ? C2 C3 H3A 110.4 . . ? C4 C3 H3A 110.4 . . ? C2 C3 H3B 110.4 . . ? C4 C3 H3B 110.4 . . ? H3A C3 H3B 108.6 . . ? N1 C4 O1 111.7(3) . . ? N1 C4 C3 103.1(3) . . ? O1 C4 C3 107.2(3) . . ? N1 C4 C5 112.9(3) . . ? O1 C4 C5 102.4(3) . . ? C3 C4 C5 119.7(3) . . ? C6 C5 C25 115.1(4) . . ? C6 C5 C26 109.6(3) . . ? C25 C5 C26 110.2(4) . . ? C6 C5 C4 99.6(3) . . ? C25 C5 C4 111.8(3) . . ? C26 C5 C4 110.1(3) . . ? C7 C6 C11 119.5(4) . . ? C7 C6 C5 131.7(3) . . ? C11 C6 C5 108.6(3) . . ? C6 C7 C8 118.9(4) . . ? C6 C7 H7A 120.5 . . ? C8 C7 H7A 120.5 . . ? C7 C8 C9 120.2(4) . . ? C7 C8 H8A 119.9 . . ? C9 C8 H8A 119.9 . . ? C8 C9 C10 122.7(4) . . ? C8 C9 H9A 118.6 . . ? C10 C9 H9A 118.6 . . ? C11 C10 C9 114.1(3) . . ? C11 C10 C12 123.1(3) . . ? C9 C10 C12 122.7(3) . . ? C6 C11 O1 111.1(3) . . ? C6 C11 C10 124.3(3) . . ? O1 C11 C10 124.6(3) . . ? C13 C12 C10 112.0(3) . . ? C13 C12 C28 108.3(3) . . ? C10 C12 C28 110.9(3) . . ? C13 C12 C27 110.0(3) . . ? C10 C12 C27 109.3(3) . . ? C28 C12 C27 106.1(3) . . ? C14 C13 N2 106.3(3) . . ? C14 C13 C12 130.1(3) . . ? N2 C13 C12 123.5(3) . . ? C13 C14 C15 108.6(4) . . ? C13 C14 H14A 125.7 . . ? C15 C14 H14A 125.7 . . ? C16 C15 C14 108.1(4) . . ? C16 C15 H15A 125.9 . . ? C14 C15 H15A 125.9 . . ? C15 C16 N2 106.3(3) . . ? C15 C16 C17 130.9(3) . . ? N2 C16 C17 122.7(3) . . ? C16 C17 C18 111.7(3) . . ? C16 C17 C29 110.5(3) . . ? C18 C17 C29 110.0(3) . . ? C16 C17 C30 107.5(3) . . ? C18 C17 C30 109.9(3) . . ? C29 C17 C30 107.0(3) . . ? C23 C18 C19 113.5(3) . . ? C23 C18 C17 123.8(3) . . ? C19 C18 C17 122.7(3) . . ? C20 C19 C18 124.0(4) . . ? C20 C19 H19A 118.0 . . ? C18 C19 H19A 118.0 . . ? C21 C20 C19 119.6(4) . . ? C21 C20 H20A 120.2 . . ? C19 C20 H20A 120.2 . . ? C20 C21 C22 118.8(4) . . ? C20 C21 H21A 120.6 . . ? C22 C21 H21A 120.6 . . ? C23 C22 C21 119.5(4) . . ? C23 C22 C24 109.8(3) . . ? C21 C22 C24 130.7(4) . . ? C22 C23 C18 124.5(3) . . ? C22 C23 O2 111.6(3) . . ? C18 C23 O2 124.0(3) . . ? C22 C24 C32 107.7(3) . . ? C22 C24 C31 114.1(4) . . ? C32 C24 C31 109.3(4) . . ? C22 C24 C1 100.2(3) . . ? C32 C24 C1 112.2(4) . . ? C31 C24 C1 113.0(3) . . ? C5 C25 H25A 109.5 . . ? C5 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C5 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C5 C26 H26A 109.5 . . ? C5 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C5 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C12 C27 H27A 109.5 . . ? C12 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C12 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C12 C28 H28A 109.5 . . ? C12 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C12 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C17 C29 H29A 109.5 . . ? C17 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C17 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C17 C30 H30A 109.5 . . ? C17 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C17 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C24 C31 H31A 109.5 . . ? C24 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C24 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C24 C32 H32A 109.5 . . ? C24 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C24 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? N1B C1B C2B 177.8(6) . . ? C1B C2B H2B1 109.5 . . ? C1B C2B H2B2 109.5 . . ? H2B1 C2B H2B2 109.5 . . ? C1B C2B H2B3 109.5 . . ? H2B1 C2B H2B3 109.5 . . ? H2B2 C2B H2B3 109.5 . . ? C11A O1A C4A 107.3(3) . . ? C23A O2A C1A 106.9(3) . . ? C1A N1A C4A 111.8(4) . . ? C1A N1A H1NA 113(3) . . ? C4A N1A H1NA 117(3) . . ? C16A N2A C13A 110.4(6) . . ? C16A N2A H2A1 124.8 . . ? C13A N2A H2A1 124.8 . . ? N1A C1A O2A 111.9(4) . . ? N1A C1A C2A 104.6(4) . . ? O2A C1A C2A 107.1(3) . . ? N1A C1A C24A 112.2(4) . . ? O2A C1A C24A 102.0(3) . . ? C2A C1A C24A 119.1(4) . . ? C1A C2A C3A 105.8(4) . . ? C1A C2A H2A2 110.6 . . ? C3A C2A H2A2 110.6 . . ? C1A C2A H2A3 110.6 . . ? C3A C2A H2A3 110.6 . . ? H2A2 C2A H2A3 108.7 . . ? C4A C3A C2A 104.7(4) . . ? C4A C3A H3A1 110.8 . . ? C2A C3A H3A1 110.8 . . ? C4A C3A H3A2 110.8 . . ? C2A C3A H3A2 110.8 . . ? H3A1 C3A H3A2 108.9 . . ? N1A C4A O1A 111.4(4) . . ? N1A C4A C3A 102.4(4) . . ? O1A C4A C3A 107.9(3) . . ? N1A C4A C5A 113.3(4) . . ? O1A C4A C5A 103.6(3) . . ? C3A C4A C5A 118.4(4) . . ? C6A C5A C26A 114.7(4) . . ? C6A C5A C25A 109.3(4) . . ? C26A C5A C25A 109.8(4) . . ? C6A C5A C4A 100.2(4) . . ? C26A C5A C4A 112.8(4) . . ? C25A C5A C4A 109.6(4) . . ? C7A C6A C11A 118.5(5) . . ? C7A C6A C5A 131.9(5) . . ? C11A C6A C5A 109.5(4) . . ? C6A C7A C8A 120.2(6) . . ? C6A C7A H7A1 119.9 . . ? C8A C7A H7A1 119.9 . . ? C7A C8A C9A 120.6(7) . . ? C7A C8A H8A1 119.7 . . ? C9A C8A H8A1 119.7 . . ? C8A C9A C10A 120.3(7) . . ? C8A C9A H9A1 119.9 . . ? C10A C9A H9A1 119.9 . . ? C11A C10A C9A 116.6(5) . . ? C11A C10A C12A 123.7(4) . . ? C9A C10A C12A 119.6(5) . . ? C6A C11A C10A 123.8(4) . . ? C6A C11A O1A 110.8(4) . . ? C10A C11A O1A 125.4(4) . . ? C13A C12A C10A 110.0(4) . . ? C13A C12A C28A 110.6(4) . . ? C10A C12A C28A 111.8(4) . . ? C13A C12A C27A 107.1(4) . . ? C10A C12A C27A 111.2(4) . . ? C28A C12A C27A 105.9(4) . . ? C14A C13A N2A 106.6(4) . . ? C14A C13A C12A 130.8(4) . . ? N2A C13A C12A 122.4(4) . . ? C13A C14A C15A 108.0(4) . . ? C13A C14A H14B 126.0 . . ? C15A C14A H14B 126.0 . . ? C16A C15A C14A 108.3(4) . . ? C16A C15A H15B 125.9 . . ? C14A C15A H15B 125.9 . . ? C15A C16A N2A 106.8(4) . . ? C15A C16A C17A 130.3(4) . . ? N2A C16A C17A 122.7(4) . . ? C16A C17A C18A 111.8(4) . . ? C16A C17A C30A 108.0(4) . . ? C18A C17A C30A 110.6(4) . . ? C16A C17A C29A 110.4(4) . . ? C18A C17A C29A 109.8(4) . . ? C30A C17A C29A 106.1(4) . . ? C23A C18A C19A 113.4(4) . . ? C23A C18A C17A 123.5(4) . . ? C19A C18A C17A 123.0(5) . . ? C20A C19A C18A 124.4(4) . . ? C20A C19A H19B 117.8 . . ? C18A C19A H19B 117.8 . . ? C21A C20A C19A 119.4(4) . . ? C21A C20A H20B 120.3 . . ? C19A C20A H20B 120.3 . . ? C22A C21A C20A 118.4(5) . . ? C22A C21A H21B 120.8 . . ? C20A C21A H21B 120.8 . . ? C21A C22A C23A 119.8(5) . . ? C21A C22A C24A 131.4(5) . . ? C23A C22A C24A 108.6(4) . . ? C18A C23A C22A 124.5(4) . . ? C18A C23A O2A 125.0(4) . . ? C22A C23A O2A 110.5(4) . . ? C22A C24A C32A 115.2(4) . . ? C22A C24A C31A 107.7(4) . . ? C32A C24A C31A 109.3(4) . . ? C22A C24A C1A 99.9(3) . . ? C32A C24A C1A 112.7(4) . . ? C31A C24A C1A 111.7(4) . . ? C11C O1C C4C 104.1(12) . . ? C23C O2C C1C 105.8(13) . . ? C1C N1C C4C 115.1(17) . . ? C13C N2C C16C 103.8(15) . . ? C13C N2C H1NA 89(3) . . ? C16C N2C H1NA 83(3) . . ? N1C C1C O2C 112.8(19) . . ? N1C C1C C2C 100.2(15) . . ? O2C C1C C2C 108.0(12) . . ? N1C C1C C24C 116.0(14) . . ? O2C C1C C24C 103.8(11) . . ? C2C C1C C24C 116.1(13) . . ? C3C C2C C1C 105.9(13) . . ? C2C C3C C4C 105.9(13) . . ? N1C C4C O1C 112.5(19) . . ? N1C C4C C3C 101.7(14) . . ? O1C C4C C3C 108.8(13) . . ? N1C C4C C5C 112.3(15) . . ? O1C C4C C5C 105.4(11) . . ? C3C C4C C5C 116.3(13) . . ? C6C C5C C25C 112.0(16) . . ? C6C C5C C26C 108.8(16) . . ? C25C C5C C26C 112.7(16) . . ? C6C C5C C4C 98.5(12) . . ? C25C C5C C4C 114.1(15) . . ? C26C C5C C4C 109.7(16) . . ? C11C C6C C7C 118.4(16) . . ? C11C C6C C5C 107.7(13) . . ? C7C C6C C5C 133.5(16) . . ? C6C C7C C8C 117.5(18) . . ? C7C C8C C9C 126.6(18) . . ? C8C C9C C10C 116.9(18) . . ? C11C C10C C9C 114.2(15) . . ? C11C C10C C12C 125.3(19) . . ? C9C C10C C12C 120.3(19) . . ? C6C C11C O1C 112.2(13) . . ? C6C C11C C10C 126.5(14) . . ? O1C C11C C10C 121.0(15) . . ? C10C C12C C13C 114.5(15) . . ? C10C C12C C28C 111.3(16) . . ? C13C C12C C28C 108.6(14) . . ? C10C C12C C27C 111.0(16) . . ? C13C C12C C27C 107.0(15) . . ? C28C C12C C27C 103.8(17) . . ? C14C C13C N2C 112.1(16) . . ? C14C C13C C12C 127.5(15) . . ? N2C C13C C12C 120.4(13) . . ? C13C C14C C15C 106.1(15) . . ? C16C C15C C14C 106.5(15) . . ? C15C C16C N2C 111.5(16) . . ? C15C C16C C17C 127.8(16) . . ? N2C C16C C17C 120.3(13) . . ? C16C C17C C18C 110.1(17) . . ? C16C C17C C30C 111.4(17) . . ? C18C C17C C30C 105.5(19) . . ? C16C C17C C29C 111.4(15) . . ? C18C C17C C29C 111.9(17) . . ? C30C C17C C29C 106.2(17) . . ? C19C C18C C23C 119(2) . . ? C19C C18C C17C 117(2) . . ? C23C C18C C17C 124(2) . . ? C20C C19C C18C 116(3) . . ? C19C C20C C21C 119(3) . . ? C22C C21C C20C 132(3) . . ? C23C C22C C21C 107(2) . . ? C23C C22C C24C 106.4(18) . . ? C21C C22C C24C 146(2) . . ? C22C C23C O2C 112.8(18) . . ? C22C C23C C18C 126.3(15) . . ? O2C C23C C18C 120.9(19) . . ? C22C C24C C31C 110.3(16) . . ? C22C C24C C32C 104.6(16) . . ? C31C C24C C32C 109.8(16) . . ? C22C C24C C1C 102.1(15) . . ? C31C C24C C1C 114.8(14) . . ? C32C C24C C1C 114.5(15) . . ? 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 C4 N1 C1 O2 -83.8(3) . . . . ? C4 N1 C1 C2 31.3(4) . . . . ? C4 N1 C1 C24 160.1(3) . . . . ? C23 O2 C1 N1 -95.9(3) . . . . ? C23 O2 C1 C2 151.1(3) . . . . ? C23 O2 C1 C24 25.1(3) . . . . ? N1 C1 C2 C3 -23.9(4) . . . . ? O2 C1 C2 C3 94.0(4) . . . . ? C24 C1 C2 C3 -149.0(4) . . . . ? C1 C2 C3 C4 10.3(5) . . . . ? C1 N1 C4 O1 90.4(3) . . . . ? C1 N1 C4 C3 -24.3(3) . . . . ? C1 N1 C4 C5 -154.8(3) . . . . ? C11 O1 C4 N1 91.2(3) . . . . ? C11 O1 C4 C3 -156.6(3) . . . . ? C11 O1 C4 C5 -29.9(3) . . . . ? C2 C3 C4 N1 7.1(4) . . . . ? C2 C3 C4 O1 -110.8(4) . . . . ? C2 C3 C4 C5 133.4(4) . . . . ? N1 C4 C5 C6 -88.2(3) . . . . ? O1 C4 C5 C6 32.0(3) . . . . ? C3 C4 C5 C6 150.2(3) . . . . ? N1 C4 C5 C25 33.9(4) . . . . ? O1 C4 C5 C25 154.1(3) . . . . ? C3 C4 C5 C25 -87.7(4) . . . . ? N1 C4 C5 C26 156.7(3) . . . . ? O1 C4 C5 C26 -83.1(3) . . . . ? C3 C4 C5 C26 35.1(4) . . . . ? C25 C5 C6 C7 40.0(6) . . . . ? C26 C5 C6 C7 -84.8(5) . . . . ? C4 C5 C6 C7 159.7(4) . . . . ? C25 C5 C6 C11 -144.7(4) . . . . ? C26 C5 C6 C11 90.5(4) . . . . ? C4 C5 C6 C11 -25.0(4) . . . . ? C11 C6 C7 C8 0.1(6) . . . . ? C5 C6 C7 C8 174.9(4) . . . . ? C6 C7 C8 C9 -3.7(7) . . . . ? C7 C8 C9 C10 2.8(7) . . . . ? C8 C9 C10 C11 1.7(6) . . . . ? C8 C9 C10 C12 -175.1(4) . . . . ? C7 C6 C11 O1 -176.5(4) . . . . ? C5 C6 C11 O1 7.5(4) . . . . ? C7 C6 C11 C10 4.9(6) . . . . ? C5 C6 C11 C10 -171.1(4) . . . . ? C4 O1 C11 C6 14.7(4) . . . . ? C4 O1 C11 C10 -166.6(3) . . . . ? C9 C10 C11 C6 -5.6(6) . . . . ? C12 C10 C11 C6 171.2(4) . . . . ? C9 C10 C11 O1 176.0(3) . . . . ? C12 C10 C11 O1 -7.3(6) . . . . ? C11 C10 C12 C13 77.7(4) . . . . ? C9 C10 C12 C13 -105.8(4) . . . . ? C11 C10 C12 C28 -161.1(4) . . . . ? C9 C10 C12 C28 15.3(5) . . . . ? C11 C10 C12 C27 -44.4(5) . . . . ? C9 C10 C12 C27 132.0(4) . . . . ? C16 N2 C13 C14 1.5(3) . . . . ? C16 N2 C13 C12 -175.0(3) . . . . ? C10 C12 C13 C14 116.5(4) . . . . ? C28 C12 C13 C14 -6.2(5) . . . . ? C27 C12 C13 C14 -121.7(4) . . . . ? C10 C12 C13 N2 -67.8(4) . . . . ? C28 C12 C13 N2 169.5(3) . . . . ? C27 C12 C13 N2 54.0(4) . . . . ? N2 C13 C14 C15 -1.4(4) . . . . ? C12 C13 C14 C15 174.9(4) . . . . ? C13 C14 C15 C16 0.8(5) . . . . ? C14 C15 C16 N2 0.2(4) . . . . ? C14 C15 C16 C17 -177.1(4) . . . . ? C13 N2 C16 C15 -1.0(3) . . . . ? C13 N2 C16 C17 176.5(4) . . . . ? C15 C16 C17 C18 -112.8(4) . . . . ? N2 C16 C17 C18 70.3(4) . . . . ? C15 C16 C17 C29 124.4(4) . . . . ? N2 C16 C17 C29 -52.5(4) . . . . ? C15 C16 C17 C30 7.9(5) . . . . ? N2 C16 C17 C30 -169.0(3) . . . . ? C16 C17 C18 C23 -79.8(4) . . . . ? C29 C17 C18 C23 43.3(5) . . . . ? C30 C17 C18 C23 160.9(4) . . . . ? C16 C17 C18 C19 100.1(4) . . . . ? C29 C17 C18 C19 -136.8(4) . . . . ? C30 C17 C18 C19 -19.2(5) . . . . ? C23 C18 C19 C20 -2.0(6) . . . . ? C17 C18 C19 C20 178.1(4) . . . . ? C18 C19 C20 C21 0.0(8) . . . . ? C19 C20 C21 C22 0.0(7) . . . . ? C20 C21 C22 C23 2.1(6) . . . . ? C20 C21 C22 C24 -176.3(4) . . . . ? C21 C22 C23 C18 -4.5(6) . . . . ? C24 C22 C23 C18 174.2(4) . . . . ? C21 C22 C23 O2 175.9(4) . . . . ? C24 C22 C23 O2 -5.4(4) . . . . ? C19 C18 C23 C22 4.3(6) . . . . ? C17 C18 C23 C22 -175.9(4) . . . . ? C19 C18 C23 O2 -176.1(3) . . . . ? C17 C18 C23 O2 3.7(6) . . . . ? C1 O2 C23 C22 -13.0(4) . . . . ? C1 O2 C23 C18 167.4(3) . . . . ? C23 C22 C24 C32 -97.3(4) . . . . ? C21 C22 C24 C32 81.2(6) . . . . ? C23 C22 C24 C31 141.1(4) . . . . ? C21 C22 C24 C31 -40.4(6) . . . . ? C23 C22 C24 C1 20.1(4) . . . . ? C21 C22 C24 C1 -161.4(4) . . . . ? N1 C1 C24 C22 93.8(3) . . . . ? O2 C1 C24 C22 -26.5(3) . . . . ? C2 C1 C24 C22 -145.4(3) . . . . ? N1 C1 C24 C32 -152.1(3) . . . . ? O2 C1 C24 C32 87.5(4) . . . . ? C2 C1 C24 C32 -31.3(5) . . . . ? N1 C1 C24 C31 -28.0(5) . . . . ? O2 C1 C24 C31 -148.4(4) . . . . ? C2 C1 C24 C31 92.8(5) . . . . ? C4A N1A C1A O2A -92.1(5) . . . . ? C4A N1A C1A C2A 23.4(6) . . . . ? C4A N1A C1A C24A 153.9(4) . . . . ? C23A O2A C1A N1A -89.9(4) . . . . ? C23A O2A C1A C2A 156.1(4) . . . . ? C23A O2A C1A C24A 30.3(4) . . . . ? N1A C1A C2A C3A -2.9(5) . . . . ? O2A C1A C2A C3A 116.0(4) . . . . ? C24A C1A C2A C3A -129.2(4) . . . . ? C1A C2A C3A C4A -16.4(5) . . . . ? C1A N1A C4A O1A 81.4(5) . . . . ? C1A N1A C4A C3A -33.7(5) . . . . ? C1A N1A C4A C5A -162.4(4) . . . . ? C11A O1A C4A N1A 95.1(4) . . . . ? C11A O1A C4A C3A -153.3(4) . . . . ? C11A O1A C4A C5A -27.0(4) . . . . ? C2A C3A C4A N1A 29.4(5) . . . . ? C2A C3A C4A O1A -88.2(4) . . . . ? C2A C3A C4A C5A 154.7(4) . . . . ? N1A C4A C5A C6A -92.7(5) . . . . ? O1A C4A C5A C6A 28.0(4) . . . . ? C3A C4A C5A C6A 147.4(4) . . . . ? N1A C4A C5A C26A 29.7(6) . . . . ? O1A C4A C5A C26A 150.4(4) . . . . ? C3A C4A C5A C26A -90.2(5) . . . . ? N1A C4A C5A C25A 152.4(5) . . . . ? O1A C4A C5A C25A -86.8(4) . . . . ? C3A C4A C5A C25A 32.5(6) . . . . ? C26A C5A C6A C7A 42.3(7) . . . . ? C25A C5A C6A C7A -81.6(6) . . . . ? C4A C5A C6A C7A 163.4(4) . . . . ? C26A C5A C6A C11A -141.9(4) . . . . ? C25A C5A C6A C11A 94.3(5) . . . . ? C4A C5A C6A C11A -20.8(5) . . . . ? C11A C6A C7A C8A -0.6(2) . . . . ? C5A C6A C7A C8A 175.0(6) . . . . ? C6A C7A C8A C9A 0.1(3) . . . . ? C7A C8A C9A C10A -0.8(5) . . . . ? C8A C9A C10A C11A 1.9(6) . . . . ? C8A C9A C10A C12A -177.0(5) . . . . ? C7A C6A C11A C10A 1.9(4) . . . . ? C5A C6A C11A C10A -174.6(5) . . . . ? C7A C6A C11A O1A -178.5(4) . . . . ? C5A C6A C11A O1A 5.0(5) . . . . ? C9A C10A C11A C6A -2.6(5) . . . . ? C12A C10A C11A C6A 176.3(5) . . . . ? C9A C10A C11A O1A 177.9(5) . . . . ? C12A C10A C11A O1A -3.2(7) . . . . ? C4A O1A C11A C6A 14.5(4) . . . . ? C4A O1A C11A C10A -165.9(4) . . . . ? C11A C10A C12A C13A 82.5(5) . . . . ? C9A C10A C12A C13A -98.6(5) . . . . ? C11A C10A C12A C28A -40.8(6) . . . . ? C9A C10A C12A C28A 138.1(5) . . . . ? C11A C10A C12A C27A -159.0(5) . . . . ? C9A C10A C12A C27A 19.9(6) . . . . ? C16A N2A C13A C14A 0.2(2) . . . . ? C16A N2A C13A C12A -175.6(5) . . . . ? C10A C12A C13A C14A 111.8(5) . . . . ? C28A C12A C13A C14A -124.1(5) . . . . ? C27A C12A C13A C14A -9.1(7) . . . . ? C10A C12A C13A N2A -73.5(5) . . . . ? C28A C12A C13A N2A 50.5(5) . . . . ? C27A C12A C13A N2A 165.5(4) . . . . ? N2A C13A C14A C15A -0.1(2) . . . . ? C12A C13A C14A C15A 175.2(5) . . . . ? C13A C14A C15A C16A 0.0(4) . . . . ? C14A C15A C16A N2A 0.2(4) . . . . ? C14A C15A C16A C17A -173.9(4) . . . . ? C13A N2A C16A C15A -0.2(4) . . . . ? C13A N2A C16A C17A 174.4(4) . . . . ? C15A C16A C17A C18A -118.6(5) . . . . ? N2A C16A C17A C18A 68.1(5) . . . . ? C15A C16A C17A C30A 3.2(6) . . . . ? N2A C16A C17A C30A -170.0(4) . . . . ? C15A C16A C17A C29A 118.8(5) . . . . ? N2A C16A C17A C29A -54.4(6) . . . . ? C16A C17A C18A C23A -77.0(5) . . . . ? C30A C17A C18A C23A 162.7(4) . . . . ? C29A C17A C18A C23A 45.9(5) . . . . ? C16A C17A C18A C19A 107.2(4) . . . . ? C30A C17A C18A C19A -13.1(5) . . . . ? C29A C17A C18A C19A -129.9(4) . . . . ? C23A C18A C19A C20A -1.9(2) . . . . ? C17A C18A C19A C20A 174.3(4) . . . . ? C18A C19A C20A C21A -1.1(2) . . . . ? C19A C20A C21A C22A 1.4(5) . . . . ? C20A C21A C22A C23A 1.3(5) . . . . ? C20A C21A C22A C24A -172.5(4) . . . . ? C19A C18A C23A C22A 4.8(4) . . . . ? C17A C18A C23A C22A -171.4(4) . . . . ? C19A C18A C23A O2A -176.0(4) . . . . ? C17A C18A C23A O2A 7.8(6) . . . . ? C21A C22A C23A C18A -4.7(6) . . . . ? C24A C22A C23A C18A 170.4(4) . . . . ? C21A C22A C23A O2A 176.0(4) . . . . ? C24A C22A C23A O2A -8.9(4) . . . . ? C1A O2A C23A C18A 166.5(3) . . . . ? C1A O2A C23A C22A -14.2(4) . . . . ? C21A C22A C24A C32A -38.0(7) . . . . ? C23A C22A C24A C32A 147.7(4) . . . . ? C21A C22A C24A C31A 84.3(6) . . . . ? C23A C22A C24A C31A -90.1(5) . . . . ? C21A C22A C24A C1A -159.0(5) . . . . ? C23A C22A C24A C1A 26.7(4) . . . . ? N1A C1A C24A C22A 86.6(4) . . . . ? O2A C1A C24A C22A -33.3(4) . . . . ? C2A C1A C24A C22A -150.9(4) . . . . ? N1A C1A C24A C32A -36.2(5) . . . . ? O2A C1A C24A C32A -156.1(4) . . . . ? C2A C1A C24A C32A 86.4(5) . . . . ? N1A C1A C24A C31A -159.8(4) . . . . ? O2A C1A C24A C31A 80.4(4) . . . . ? C2A C1A C24A C31A -37.2(6) . . . . ? C4C N1C C1C O2C -79(3) . . . . ? C4C N1C C1C C2C 36(3) . . . . ? C4C N1C C1C C24C 162(2) . . . . ? C23C O2C C1C N1C -99.2(17) . . . . ? C23C O2C C1C C2C 151.0(14) . . . . ? C23C O2C C1C C24C 27.1(16) . . . . ? N1C C1C C2C C3C -27(2) . . . . ? O2C C1C C2C C3C 91.1(16) . . . . ? C24C C1C C2C C3C -152.8(14) . . . . ? C1C C2C C3C C4C 12.3(18) . . . . ? C1C N1C C4C O1C 88(3) . . . . ? C1C N1C C4C C3C -28(3) . . . . ? C1C N1C C4C C5C -153(2) . . . . ? C11C O1C C4C N1C 94.4(15) . . . . ? C11C O1C C4C C3C -153.7(13) . . . . ? C11C O1C C4C C5C -28.3(15) . . . . ? C2C C3C C4C N1C 7(2) . . . . ? C2C C3C C4C O1C -111.4(15) . . . . ? C2C C3C C4C C5C 129.8(15) . . . . ? N1C C4C C5C C6C -89(2) . . . . ? O1C C4C C5C C6C 34.2(15) . . . . ? C3C C4C C5C C6C 154.8(13) . . . . ? N1C C4C C5C C25C 30(2) . . . . ? O1C C4C C5C C25C 153.0(15) . . . . ? C3C C4C C5C C25C -86.4(19) . . . . ? N1C C4C C5C C26C 158(2) . . . . ? O1C C4C C5C C26C -79.4(17) . . . . ? C3C C4C C5C C26C 41.2(19) . . . . ? C25C C5C C6C C11C -148.3(14) . . . . ? C26C C5C C6C C11C 86.4(16) . . . . ? C4C C5C C6C C11C -27.9(14) . . . . ? C25C C5C C6C C7C 39(2) . . . . ? C26C C5C C6C C7C -86(2) . . . . ? C4C C5C C6C C7C 159.6(13) . . . . ? C11C C6C C7C C8C -0.3(3) . . . . ? C5C C6C C7C C8C 171.5(18) . . . . ? C6C C7C C8C C9C -0.2(3) . . . . ? C7C C8C C9C C10C 0.1(7) . . . . ? C8C C9C C10C C11C 0.4(8) . . . . ? C8C C9C C10C C12C -174.5(16) . . . . ? C7C C6C C11C O1C -173.7(14) . . . . ? C5C C6C C11C O1C 12.5(14) . . . . ? C7C C6C C11C C10C 0.9(8) . . . . ? C5C C6C C11C C10C -172.9(14) . . . . ? C4C O1C C11C C6C 10.6(14) . . . . ? C4C O1C C11C C10C -164.4(11) . . . . ? C9C C10C C11C C6C -0.9(9) . . . . ? C12C C10C C11C C6C 173.6(17) . . . . ? C9C C10C C11C O1C 173.3(15) . . . . ? C12C C10C C11C O1C -12.2(18) . . . . ? C11C C10C C12C C13C 77.5(18) . . . . ? C9C C10C C12C C13C -108.3(15) . . . . ? C11C C10C C12C C28C -158.8(14) . . . . ? C9C C10C C12C C28C 15(2) . . . . ? C11C C10C C12C C27C -44(2) . . . . ? C9C C10C C12C C27C 130.5(16) . . . . ? C16C N2C C13C C14C 0.1(3) . . . . ? C16C N2C C13C C12C -179.5(16) . . . . ? C10C C12C C13C C14C 118.2(18) . . . . ? C28C C12C C13C C14C -7(2) . . . . ? C27C C12C C13C C14C -118.4(18) . . . . ? C10C C12C C13C N2C -62.3(19) . . . . ? C28C C12C C13C N2C 172.7(13) . . . . ? C27C C12C C13C N2C 61.2(18) . . . . ? N2C C13C C14C C15C 0.1(3) . . . . ? C12C C13C C14C C15C 179.7(17) . . . . ? C13C C14C C15C C16C -0.3(5) . . . . ? C14C C15C C16C N2C 0.4(7) . . . . ? C14C C15C C16C C17C -171.3(17) . . . . ? C13C N2C C16C C15C -0.3(5) . . . . ? C13C N2C C16C C17C 172.0(16) . . . . ? C15C C16C C17C C18C -113(2) . . . . ? N2C C16C C17C C18C 75.6(19) . . . . ? C15C C16C C17C C30C 3(2) . . . . ? N2C C16C C17C C30C -167.6(15) . . . . ? C15C C16C C17C C29C 121.9(17) . . . . ? N2C C16C C17C C29C -49(2) . . . . ? C16C C17C C18C C19C 100.7(17) . . . . ? C30C C17C C18C C19C -20(2) . . . . ? C29C C17C C18C C19C -134.8(17) . . . . ? C16C C17C C18C C23C -82(2) . . . . ? C30C C17C C18C C23C 157.2(18) . . . . ? C29C C17C C18C C23C 42(2) . . . . ? C23C C18C C19C C20C -0.1(3) . . . . ? C17C C18C C19C C20C 177(2) . . . . ? C18C C19C C20C C21C -0.1(3) . . . . ? C19C C20C C21C C22C 0.1(9) . . . . ? C20C C21C C22C C23C 0.1(10) . . . . ? C20C C21C C22C C24C -174(3) . . . . ? C21C C22C C23C O2C 178.2(19) . . . . ? C24C C22C C23C O2C -5.4(19) . . . . ? C21C C22C C23C C18C -0.4(9) . . . . ? C24C C22C C23C C18C 176.1(18) . . . . ? C1C O2C C23C C22C -14.5(18) . . . . ? C1C O2C C23C C18C 164.1(13) . . . . ? C19C C18C C23C C22C 0.4(8) . . . . ? C17C C18C C23C C22C -176(2) . . . . ? C19C C18C C23C O2C -178(2) . . . . ? C17C C18C C23C O2C 5(2) . . . . ? C23C C22C C24C C31C 143.8(16) . . . . ? C21C C22C C24C C31C -42(3) . . . . ? C23C C22C C24C C32C -98.3(17) . . . . ? C21C C22C C24C C32C 76(3) . . . . ? C23C C22C C24C C1C 21.4(17) . . . . ? C21C C22C C24C C1C -165(2) . . . . ? N1C C1C C24C C22C 95(2) . . . . ? O2C C1C C24C C22C -29.6(16) . . . . ? C2C C1C C24C C22C -148.0(14) . . . . ? N1C C1C C24C C31C -25(2) . . . . ? O2C C1C C24C C31C -148.9(15) . . . . ? C2C C1C C24C C31C 92.7(18) . . . . ? N1C C1C C24C C32C -153(2) . . . . ? O2C C1C C24C C32C 82.7(17) . . . . ? C2C C1C C24C C32C -36(2) . . . . ? 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 N1 H1N N1B 0.85(4) 2.20(4) 3.043(4) 174(4) . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.261 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.038 #===END data_4 _database_code_depnum_ccdc_archive 'CCDC 858003' #TrackingRef '- combo-ChemComm 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H38 N2 O2' _chemical_formula_sum 'C32 H38 N2 O2' _chemical_formula_weight 482.64 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.3075(2) _cell_length_b 17.5050(4) _cell_length_c 9.9498(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.307(1) _cell_angle_gamma 90.00 _cell_volume 1272.43(6) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 2884 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description prisms _exptl_crystal_colour 'light brown' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.260 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 'Nonius Kappa CCD' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5334 _diffrn_reflns_av_R_equivalents 0.0184 _diffrn_reflns_av_sigmaI/netI 0.0321 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 27.43 _reflns_number_total 2892 _reflns_number_gt 2323 _reflns_threshold_expression >2sigma(I) _publ_section_references ; Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. Sir97. (1999) J. Appl. Cryst. 32, 115-119. Otwinowski, Z. and Minor, W. (1997). Methods in Enzymology, 276, Macromolecular Crystallography, part A, 307-326, C. W. Carter, Jr. and R. M. Sweets, Eds., Academic Press. Sheldrick, G. M. (1998). SHELXTL/PC. Release 5.10. Siemens Analytical X-ray Instruments, Inc., Madison, WI, USA. ; _computing_data_collection 'Collect software, Nonius B.V. 1998' _computing_cell_refinement 'Collect software, Nonius B.V. 1998' _computing_data_reduction ; DENZO and Scalepack (Otwinoski and Minor, 1997) ; _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _computing_publication_material ? _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^)+(0.0590P)^2^+0.4715P] 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 refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.013(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2892 _refine_ls_number_parameters 240 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0555 _refine_ls_R_factor_gt 0.0417 _refine_ls_wR_factor_ref 0.1164 _refine_ls_wR_factor_gt 0.1076 _refine_ls_goodness_of_fit_ref 0.986 _refine_ls_restrained_S_all 0.986 _refine_ls_shift/su_max 0.028 _refine_ls_shift/su_mean 0.005 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 O1 O 1.23114(13) 0.56528(7) 0.54408(12) 0.0395(3) Uani 1 1 d . . . N1 N 0.51532(15) 0.55788(6) 0.28805(11) 0.0247(3) Uani 1 1 d . . . C1 C 0.36745(17) 0.53086(7) 0.21351(13) 0.0241(3) Uani 1 1 d . . . C2 C 0.26802(19) 0.59341(8) 0.17174(14) 0.0296(3) Uani 1 1 d . . . C3 C 0.35775(19) 0.65984(8) 0.22200(14) 0.0298(3) Uani 1 1 d . . . C4 C 0.51068(18) 0.63717(7) 0.29332(13) 0.0251(3) Uani 1 1 d . . . C5 C 0.66942(18) 0.68499(7) 0.34781(13) 0.0262(3) Uani 1 1 d . . . C6 C 0.77439(17) 0.64285(7) 0.46004(13) 0.0244(3) Uani 1 1 d . . . C7 C 0.68354(18) 0.62140(7) 0.57705(13) 0.0238(3) Uani 1 1 d . . . C8 C 0.77336(17) 0.58242(7) 0.68100(13) 0.0235(3) Uani 1 1 d . . . C9 C 0.95917(18) 0.56440(8) 0.66773(14) 0.0278(3) Uani 1 1 d . . . C10 C 1.04907(18) 0.58576(8) 0.55296(14) 0.0292(3) Uani 1 1 d . . . C11 C 0.95892(18) 0.62487(8) 0.44966(14) 0.0279(3) Uani 1 1 d . . . C12 C 0.67101(18) 0.55383(7) 0.80565(13) 0.0251(3) Uani 1 1 d . . . C13 C 0.7914(2) 0.70326(9) 0.22720(15) 0.0343(4) Uani 1 1 d . . . C14 C 0.5968(2) 0.76087(8) 0.40286(16) 0.0356(4) Uani 1 1 d . . . C15 C 0.4934(2) 0.59787(8) 0.82817(16) 0.0317(3) Uani 1 1 d . . . C16 C 0.7913(2) 0.56416(10) 0.93337(15) 0.0349(4) Uani 1 1 d . . . H12N H 0.606(2) 0.5282(10) 0.3312(17) 0.038(4) Uiso 1 1 d . . . H2A H 0.152(2) 0.5926(9) 0.1176(17) 0.038(4) Uiso 1 1 d . . . H3A H 0.322(2) 0.7131(11) 0.2060(18) 0.043(5) Uiso 1 1 d . . . H7A H 0.554(2) 0.6339(9) 0.5862(15) 0.029(4) Uiso 1 1 d . . . H9A H 1.026(2) 0.5348(9) 0.7378(17) 0.032(4) Uiso 1 1 d . . . H11A H 1.027(2) 0.6382(10) 0.3700(17) 0.038(4) Uiso 1 1 d . . . H13A H 0.838(2) 0.6539(10) 0.1847(18) 0.043(5) Uiso 1 1 d . . . H13B H 0.712(2) 0.7306(9) 0.1629(16) 0.030(4) Uiso 1 1 d . . . H13C H 0.900(2) 0.7358(10) 0.2568(17) 0.042(5) Uiso 1 1 d . . . H14A H 0.505(2) 0.7503(9) 0.4735(17) 0.036(4) Uiso 1 1 d . . . H14B H 0.699(2) 0.7923(10) 0.4370(17) 0.038(4) Uiso 1 1 d . . . H14C H 0.533(3) 0.7900(11) 0.333(2) 0.052(5) Uiso 1 1 d . . . H15A H 0.401(2) 0.5929(10) 0.7528(19) 0.041(5) Uiso 1 1 d . . . H15B H 0.432(2) 0.5799(10) 0.9088(19) 0.041(4) Uiso 1 1 d . . . H15C H 0.528(2) 0.6532(10) 0.8439(17) 0.038(4) Uiso 1 1 d . . . H16A H 0.726(2) 0.5481(10) 1.0105(18) 0.040(5) Uiso 1 1 d . . . H16B H 0.905(2) 0.5371(10) 0.9287(18) 0.040(5) Uiso 1 1 d . . . H16C H 0.817(2) 0.6194(11) 0.9494(18) 0.046(5) Uiso 1 1 d . . . H1O H 1.265(4) 0.5776(16) 0.463(3) 0.098(9) 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 O1 0.0223(5) 0.0584(7) 0.0379(6) -0.0037(5) 0.0035(4) 0.0004(5) N1 0.0273(6) 0.0236(6) 0.0232(6) 0.0007(4) -0.0013(4) -0.0002(4) C1 0.0246(6) 0.0277(7) 0.0202(6) 0.0010(5) 0.0020(5) -0.0016(5) C2 0.0286(7) 0.0326(7) 0.0275(7) 0.0040(6) -0.0020(5) 0.0021(6) C3 0.0342(7) 0.0253(7) 0.0299(7) 0.0047(5) 0.0010(6) 0.0035(6) C4 0.0316(7) 0.0219(6) 0.0221(6) 0.0016(5) 0.0042(5) 0.0001(5) C5 0.0334(7) 0.0234(6) 0.0219(6) 0.0003(5) 0.0028(5) -0.0034(5) C6 0.0291(7) 0.0217(6) 0.0226(6) -0.0033(5) 0.0017(5) -0.0046(5) C7 0.0245(6) 0.0236(6) 0.0235(7) -0.0017(5) 0.0020(5) -0.0029(5) C8 0.0267(6) 0.0222(6) 0.0217(6) -0.0033(5) 0.0011(5) -0.0038(5) C9 0.0273(7) 0.0303(7) 0.0255(7) -0.0018(6) -0.0030(5) -0.0016(5) C10 0.0223(6) 0.0337(7) 0.0315(7) -0.0074(6) 0.0012(5) -0.0035(5) C11 0.0286(7) 0.0320(7) 0.0233(7) -0.0036(5) 0.0055(5) -0.0072(6) C12 0.0288(7) 0.0265(7) 0.0201(6) 0.0002(5) 0.0009(5) -0.0016(5) C13 0.0422(8) 0.0350(8) 0.0258(7) 0.0027(6) 0.0043(6) -0.0099(7) C14 0.0515(10) 0.0245(7) 0.0309(8) -0.0009(6) 0.0011(7) 0.0024(7) C15 0.0382(8) 0.0286(7) 0.0287(8) 0.0007(6) 0.0119(6) 0.0011(6) C16 0.0431(9) 0.0390(9) 0.0224(7) -0.0002(6) -0.0033(6) -0.0113(7) _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 O1 C10 1.3827(16) . ? O1 H1O 0.88(3) . ? N1 C1 1.3801(17) . ? N1 C4 1.3894(17) . ? N1 H12N 0.937(18) . ? C1 C2 1.3732(19) . ? C1 C12 1.5202(18) 3_666 ? C2 C3 1.420(2) . ? C2 H2A 0.997(18) . ? C3 C4 1.3688(19) . ? C3 H3A 0.980(18) . ? C4 C5 1.5204(19) . ? C5 C6 1.5298(19) . ? C5 C14 1.5361(19) . ? C5 C13 1.5446(18) . ? C6 C11 1.3908(18) . ? C6 C7 1.4045(17) . ? C7 C8 1.3911(19) . ? C7 H7A 0.980(16) . ? C8 C9 1.4031(18) . ? C8 C12 1.5461(17) . ? C9 C10 1.382(2) . ? C9 H9A 0.989(17) . ? C10 C11 1.389(2) . ? C11 H11A 0.974(17) . ? C12 C1 1.5202(18) 3_666 ? C12 C15 1.531(2) . ? C12 C16 1.5392(19) . ? C13 H13A 1.024(18) . ? C13 H13B 0.980(16) . ? C13 H13C 1.017(18) . ? C14 H14A 0.998(17) . ? C14 H14B 0.983(18) . ? C14 H14C 0.97(2) . ? C15 H15A 1.002(19) . ? C15 H15B 0.978(19) . ? C15 H15C 1.012(18) . ? C16 H16A 0.954(18) . ? C16 H16B 0.959(18) . ? C16 H16C 0.998(19) . ? 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 C10 O1 H1O 106.7(18) . . ? C1 N1 C4 110.06(11) . . ? C1 N1 H12N 126.3(10) . . ? C4 N1 H12N 123.6(10) . . ? C2 C1 N1 106.97(12) . . ? C2 C1 C12 130.14(12) . 3_666 ? N1 C1 C12 122.81(11) . 3_666 ? C1 C2 C3 108.02(12) . . ? C1 C2 H2A 126.3(10) . . ? C3 C2 H2A 125.7(9) . . ? C4 C3 C2 108.06(12) . . ? C4 C3 H3A 124.7(10) . . ? C2 C3 H3A 127.2(10) . . ? C3 C4 N1 106.88(12) . . ? C3 C4 C5 129.23(12) . . ? N1 C4 C5 122.98(12) . . ? C4 C5 C6 111.14(10) . . ? C4 C5 C14 109.64(12) . . ? C6 C5 C14 109.17(11) . . ? C4 C5 C13 106.62(11) . . ? C6 C5 C13 112.23(12) . . ? C14 C5 C13 107.95(12) . . ? C11 C6 C7 118.59(12) . . ? C11 C6 C5 121.72(11) . . ? C7 C6 C5 119.69(11) . . ? C8 C7 C6 121.57(12) . . ? C8 C7 H7A 118.8(9) . . ? C6 C7 H7A 119.6(9) . . ? C7 C8 C9 118.78(12) . . ? C7 C8 C12 121.77(11) . . ? C9 C8 C12 119.32(12) . . ? C10 C9 C8 119.75(13) . . ? C10 C9 H9A 119.2(9) . . ? C8 C9 H9A 121.0(9) . . ? C9 C10 C11 121.24(12) . . ? C9 C10 O1 117.32(13) . . ? C11 C10 O1 121.43(13) . . ? C10 C11 C6 120.07(12) . . ? C10 C11 H11A 118.5(10) . . ? C6 C11 H11A 121.4(10) . . ? C1 C12 C15 110.77(11) 3_666 . ? C1 C12 C16 108.57(11) 3_666 . ? C15 C12 C16 106.87(12) . . ? C1 C12 C8 107.85(10) 3_666 . ? C15 C12 C8 112.45(11) . . ? C16 C12 C8 110.29(11) . . ? C5 C13 H13A 110.4(10) . . ? C5 C13 H13B 105.3(9) . . ? H13A C13 H13B 109.9(13) . . ? C5 C13 H13C 110.7(10) . . ? H13A C13 H13C 109.2(14) . . ? H13B C13 H13C 111.3(13) . . ? C5 C14 H14A 109.4(9) . . ? C5 C14 H14B 109.9(10) . . ? H14A C14 H14B 112.2(13) . . ? C5 C14 H14C 111.2(12) . . ? H14A C14 H14C 106.7(14) . . ? H14B C14 H14C 107.5(15) . . ? C12 C15 H15A 114.0(10) . . ? C12 C15 H15B 111.2(10) . . ? H15A C15 H15B 105.9(14) . . ? C12 C15 H15C 107.1(9) . . ? H15A C15 H15C 111.1(14) . . ? H15B C15 H15C 107.3(14) . . ? C12 C16 H16A 110.1(10) . . ? C12 C16 H16B 112.4(11) . . ? H16A C16 H16B 110.0(15) . . ? C12 C16 H16C 110.4(10) . . ? H16A C16 H16C 104.6(15) . . ? H16B C16 H16C 108.9(15) . . ? 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 C4 N1 C1 C2 -0.25(14) . . . . ? C4 N1 C1 C12 -177.14(11) . . . 3_666 ? N1 C1 C2 C3 0.05(15) . . . . ? C12 C1 C2 C3 176.64(13) 3_666 . . . ? C1 C2 C3 C4 0.17(16) . . . . ? C2 C3 C4 N1 -0.31(15) . . . . ? C2 C3 C4 C5 168.88(13) . . . . ? C1 N1 C4 C3 0.35(15) . . . . ? C1 N1 C4 C5 -169.67(11) . . . . ? C3 C4 C5 C6 160.24(13) . . . . ? N1 C4 C5 C6 -32.11(16) . . . . ? C3 C4 C5 C14 39.46(18) . . . . ? N1 C4 C5 C14 -152.89(12) . . . . ? C3 C4 C5 C13 -77.16(17) . . . . ? N1 C4 C5 C13 90.49(15) . . . . ? C4 C5 C6 C11 119.65(13) . . . . ? C14 C5 C6 C11 -119.29(14) . . . . ? C13 C5 C6 C11 0.35(17) . . . . ? C4 C5 C6 C7 -60.31(15) . . . . ? C14 C5 C6 C7 60.75(15) . . . . ? C13 C5 C6 C7 -179.60(12) . . . . ? C11 C6 C7 C8 -0.54(19) . . . . ? C5 C6 C7 C8 179.42(11) . . . . ? C6 C7 C8 C9 0.05(19) . . . . ? C6 C7 C8 C12 -175.74(11) . . . . ? C7 C8 C9 C10 0.26(19) . . . . ? C12 C8 C9 C10 176.15(12) . . . . ? C8 C9 C10 C11 -0.1(2) . . . . ? C8 C9 C10 O1 -178.81(12) . . . . ? C9 C10 C11 C6 -0.4(2) . . . . ? O1 C10 C11 C6 178.26(12) . . . . ? C7 C6 C11 C10 0.72(19) . . . . ? C5 C6 C11 C10 -179.23(12) . . . . ? C7 C8 C12 C1 100.04(14) . . . 3_666 ? C9 C8 C12 C1 -75.73(14) . . . 3_666 ? C7 C8 C12 C15 -22.37(17) . . . . ? C9 C8 C12 C15 161.85(12) . . . . ? C7 C8 C12 C16 -141.55(13) . . . . ? C9 C8 C12 C16 42.68(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 N1 H12N O1 0.937(18) 2.361(18) 3.2756(17) 165.4(14) 3_766 O1 H1O N1 0.88(3) 2.58(3) 3.3257(16) 144(2) 1_655 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.43 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.253 _refine_diff_density_min -0.211 _refine_diff_density_rms 0.044 #===END data_(4)2-H _database_code_depnum_ccdc_archive 'CCDC 858004' #TrackingRef '- combo-ChemComm 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; C32 H38 N2 O2, C32 H37 N2 O2 1-, F 1-, 2 C16 H36 N 1+, H2 O, 3 C H2 Cl2 ; _chemical_formula_sum 'C99 H155 Cl6 F N6 O5' _chemical_formula_weight 1740.99 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' 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 I2/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z' '-x+1/2, -y+1/2, -z+1/2' 'x, -y+1/2, z+1/2' _cell_length_a 29.8044(8) _cell_length_b 10.3800(5) _cell_length_c 31.855(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.290(2) _cell_angle_gamma 90.00 _cell_volume 9813.1(8) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 18376 _cell_measurement_theta_min 1.7 _cell_measurement_theta_max 27.5 _exptl_crystal_description plates _exptl_crystal_colour colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.178 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3768 _exptl_absorpt_coefficient_mu 0.230 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.903 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details ; DENZO and Scalepack (Otwinoski and Minor, 1997) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18633 _diffrn_reflns_av_R_equivalents 0.0493 _diffrn_reflns_av_sigmaI/netI 0.0977 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -41 _diffrn_reflns_limit_l_max 41 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 27.50 _reflns_number_total 10914 _reflns_number_gt 5835 _reflns_threshold_expression >2sigma(I) _publ_section_references ; Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. Sir97. (1999) J. Appl. Cryst. 32, 115-119. Farrugia, L. J. (1999) J. Appl. Cryst., 32, 837-838. An Integrated System of Windows Programs for the Solution, Refinement and Analysis of Single Crystal X-ray Diffraction Data. Otwinowski, Z. and Minor, W. (1997). Methods in Enzymology, 276, Macromolecular Crystallography, part A, 307-326, C. W. Carter, Jr. and R. M. Sweets, Eds., Academic Press. Sheldrick, G. M. (2008). SHELXL-97. Acat Cryst., A64, 112-122. Spek, A. L. (1998) PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands. ; _computing_data_collection 'Collect software, Nonius B.V. 1998' _computing_cell_refinement 'Collect software, Nonius B.V. 1998' _computing_data_reduction ; DENZO and Scalepack (Otwinoski and Minor, 1997) ; _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _computing_publication_material ? _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. The fluoride ion resides on a crystallographic two-fold rotation axis. Because the fluoride ion resides on a two-fold and the tetrakis- n-butyl ammonium ion is in a general position, requires that a second ion be present to maintain charge neutrality. It appears that one hydroxyl group on the dipyrrole is deprotonated in the H-bound complex. It appears that O1 is the hydroxyl oxygen that is deprotonated. The cation has some disorder on one n-butyl chain. The disorder involves the terminal CH2-CH3 atoms, C15a and C16a. The disorder was modeled by assigning the variable x to the site occupancy factors for one component of the disorder and (1-x) to the site occupancy factors for the alternate component. In addition, geometric restraints were applied to the atoms involved and a common isotropic displacement parameter was refined while refining x. In this way, the site occupancy factor for C15a and C16a refined to 78(2)%. One of the dichloromethane molecules was disordered about a crystallographic two-fold rotation axis. No hydrogen atoms were calculated for this molecule. In addition, a water molecule was found to be H-bound to the fluoride ion but did not have enough e- density to constitute a full oxygen atom. The site occupancy for this atom, O1w, was assigned to 1/2. ; _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^)+(0.1000P)^2^+] 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 10914 _refine_ls_number_parameters 562 _refine_ls_number_restraints 68 _refine_ls_R_factor_all 0.1623 _refine_ls_R_factor_gt 0.0831 _refine_ls_wR_factor_ref 0.2553 _refine_ls_wR_factor_gt 0.2221 _refine_ls_goodness_of_fit_ref 1.366 _refine_ls_restrained_S_all 1.382 _refine_ls_shift/su_max 0.006 _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 Cl1B Cl 0.56671(4) 0.34836(12) 0.77701(4) 0.0603(4) Uani 1 1 d . . . Cl2B Cl 0.66145(4) 0.27972(12) 0.77862(4) 0.0584(4) Uani 1 1 d . . . O1 O 0.50370(9) 0.3912(2) 0.51526(8) 0.0344(6) Uani 1 1 d . . . H1O H 0.5068 0.4661 0.5059 0.052 Uiso 0.50 1 calc PR . . O2 O 0.70813(9) 0.2361(3) 0.53071(8) 0.0417(7) Uani 1 1 d . . . H2O H 0.7230 0.2998 0.5235 0.063 Uiso 1 1 calc R . . N1 N 0.58334(9) 0.1061(3) 0.65021(9) 0.0254(6) Uani 1 1 d . . . H1N H 0.5861 0.1445 0.6260 0.031 Uiso 1 1 calc R . . N2 N 0.62854(9) 0.5438(3) 0.65199(9) 0.0256(6) Uani 1 1 d . . . H2N H 0.6257 0.5134 0.6261 0.031 Uiso 1 1 calc R . . C1 C 0.61760(11) 0.0414(3) 0.67369(10) 0.0228(7) Uani 1 1 d . . . C2 C 0.59985(12) -0.0049(3) 0.70800(11) 0.0308(8) Uani 1 1 d . . . H2 H 0.6154 -0.0540 0.7299 0.037 Uiso 1 1 calc R . . C3 C 0.55383(12) 0.0323(3) 0.70586(11) 0.0314(8) Uani 1 1 d . . . H3 H 0.5332 0.0119 0.7259 0.038 Uiso 1 1 calc R . . C4 C 0.54449(11) 0.1022(3) 0.66997(11) 0.0249(8) Uani 1 1 d . . . C5 C 0.50046(11) 0.1548(3) 0.64933(11) 0.0267(8) Uani 1 1 d . . . C6 C 0.50933(10) 0.2770(3) 0.62368(11) 0.0243(8) Uani 1 1 d . . . C7 C 0.52525(10) 0.3878(3) 0.64512(11) 0.0236(7) Uani 1 1 d . . . H7 H 0.5312 0.3856 0.6749 0.028 Uiso 1 1 calc R . . C8 C 0.53260(10) 0.5017(3) 0.62347(11) 0.0217(7) Uani 1 1 d . . . C9 C 0.52508(10) 0.5027(3) 0.57987(11) 0.0254(8) Uani 1 1 d . . . H9 H 0.5298 0.5801 0.5650 0.030 Uiso 1 1 calc R . . C10 C 0.51065(11) 0.3925(3) 0.55727(11) 0.0268(8) Uani 1 1 d . . . C11 C 0.50239(11) 0.2800(3) 0.58008(11) 0.0256(8) Uani 1 1 d . . . H11 H 0.4919 0.2048 0.5653 0.031 Uiso 1 1 calc R . . C12 C 0.54853(11) 0.6230(3) 0.64870(11) 0.0246(8) Uani 1 1 d . . . C13 C 0.59439(11) 0.6003(3) 0.67169(11) 0.0221(7) Uani 1 1 d . . . C14 C 0.61247(11) 0.6336(3) 0.71098(11) 0.0289(8) Uani 1 1 d . . . H14 H 0.5970 0.6743 0.7321 0.035 Uiso 1 1 calc R . . C15 C 0.65863(12) 0.5967(3) 0.71480(11) 0.0305(8) Uani 1 1 d . . . H15 H 0.6794 0.6091 0.7389 0.037 Uiso 1 1 calc R . . C16 C 0.66773(10) 0.5412(3) 0.67831(11) 0.0248(8) Uani 1 1 d . . . C17 C 0.71137(11) 0.4912(3) 0.66292(12) 0.0287(8) Uani 1 1 d . . . C18 C 0.70227(10) 0.3677(3) 0.63685(11) 0.0268(8) Uani 1 1 d . . . C19 C 0.68586(11) 0.2585(3) 0.65620(11) 0.0259(8) Uani 1 1 d . . . H19 H 0.6800 0.2630 0.6850 0.031 Uiso 1 1 calc R . . C20 C 0.67779(10) 0.1421(3) 0.63402(11) 0.0254(8) Uani 1 1 d . . . C21 C 0.68497(11) 0.1392(3) 0.59191(11) 0.0283(8) Uani 1 1 d . . . H21 H 0.6788 0.0625 0.5762 0.034 Uiso 1 1 calc R . . C22 C 0.70103(11) 0.2469(4) 0.57213(11) 0.0294(8) Uani 1 1 d . . . C23 C 0.70994(11) 0.3605(3) 0.59421(12) 0.0289(8) Uani 1 1 d . . . H23 H 0.7212 0.4332 0.5805 0.035 Uiso 1 1 calc R . . C24 C 0.66383(11) 0.0229(3) 0.65772(11) 0.0267(8) Uani 1 1 d . . . C25 C 0.47731(12) 0.0475(3) 0.62150(12) 0.0353(9) Uani 1 1 d . . . H25A H 0.4971 0.0211 0.6002 0.053 Uiso 1 1 calc R . . H25B H 0.4489 0.0801 0.6075 0.053 Uiso 1 1 calc R . . H25C H 0.4712 -0.0267 0.6391 0.053 Uiso 1 1 calc R . . C26 C 0.46897(13) 0.1875(4) 0.68368(13) 0.0406(10) Uani 1 1 d . . . H26A H 0.4653 0.1112 0.7012 0.061 Uiso 1 1 calc R . . H26B H 0.4395 0.2143 0.6703 0.061 Uiso 1 1 calc R . . H26C H 0.4821 0.2576 0.7014 0.061 Uiso 1 1 calc R . . C27 C 0.51451(12) 0.6534(4) 0.68107(12) 0.0343(9) Uani 1 1 d . . . H27A H 0.5135 0.5813 0.7008 0.051 Uiso 1 1 calc R . . H27B H 0.4845 0.6665 0.6663 0.051 Uiso 1 1 calc R . . H27C H 0.5239 0.7318 0.6966 0.051 Uiso 1 1 calc R . . C28 C 0.55116(12) 0.7423(3) 0.62029(12) 0.0326(9) Uani 1 1 d . . . H28A H 0.5600 0.8175 0.6377 0.049 Uiso 1 1 calc R . . H28B H 0.5216 0.7577 0.6049 0.049 Uiso 1 1 calc R . . H28C H 0.5736 0.7274 0.6001 0.049 Uiso 1 1 calc R . . C29 C 0.73163(12) 0.6001(4) 0.63734(13) 0.0381(9) Uani 1 1 d . . . H29A H 0.7104 0.6226 0.6131 0.057 Uiso 1 1 calc R . . H29B H 0.7600 0.5706 0.6273 0.057 Uiso 1 1 calc R . . H29C H 0.7373 0.6759 0.6554 0.057 Uiso 1 1 calc R . . C30 C 0.74499(12) 0.4609(4) 0.70112(13) 0.0382(10) Uani 1 1 d . . . H30A H 0.7504 0.5388 0.7182 0.057 Uiso 1 1 calc R . . H30B H 0.7734 0.4311 0.6913 0.057 Uiso 1 1 calc R . . H30C H 0.7326 0.3933 0.7182 0.057 Uiso 1 1 calc R . . C31 C 0.69856(12) -0.0031(4) 0.69555(12) 0.0362(9) Uani 1 1 d . . . H31A H 0.7285 -0.0138 0.6856 0.054 Uiso 1 1 calc R . . H31B H 0.6903 -0.0819 0.7100 0.054 Uiso 1 1 calc R . . H31C H 0.6990 0.0697 0.7152 0.054 Uiso 1 1 calc R . . C32 C 0.66160(12) -0.0982(3) 0.62982(13) 0.0350(9) Uani 1 1 d . . . H32A H 0.6395 -0.0850 0.6054 0.052 Uiso 1 1 calc R . . H32B H 0.6525 -0.1723 0.6462 0.052 Uiso 1 1 calc R . . H32C H 0.6913 -0.1147 0.6201 0.052 Uiso 1 1 calc R . . C1B C 0.61109(13) 0.3130(4) 0.74676(12) 0.0381(9) Uani 1 1 d . . . H1BA H 0.6161 0.3870 0.7281 0.046 Uiso 1 1 calc R . . H1BB H 0.6029 0.2375 0.7287 0.046 Uiso 1 1 calc R . . F1 F 0.7500 0.4137(3) 0.5000 0.0520(9) Uani 1 2 d S . . O1W O 0.7250(3) 0.6056(8) 0.4539(3) 0.090(2) Uani 0.50 1 d P . . N1AA N 0.62052(9) 0.3241(3) 0.43305(10) 0.0357(8) Uani 1 1 d . . . C1A C 0.60150(13) 0.3836(4) 0.39162(14) 0.0469(11) Uani 1 1 d . . . H1AA H 0.5928 0.3130 0.3716 0.056 Uiso 1 1 calc R . . H1AB H 0.5737 0.4311 0.3966 0.056 Uiso 1 1 calc R . . C2A C 0.63217(14) 0.4736(5) 0.37113(15) 0.0522(12) Uani 1 1 d . . . H2AA H 0.6591 0.4258 0.3639 0.063 Uiso 1 1 calc R . . H2AB H 0.6423 0.5426 0.3913 0.063 Uiso 1 1 calc R . . C3A C 0.60907(15) 0.5327(4) 0.33196(15) 0.0531(12) Uani 1 1 d . . . H3AA H 0.5804 0.5721 0.3388 0.064 Uiso 1 1 calc R . . H3AB H 0.6018 0.4642 0.3108 0.064 Uiso 1 1 calc R . . C4A C 0.63753(15) 0.6343(4) 0.31311(15) 0.0542(12) Uani 1 1 d . . . H4A1 H 0.6477 0.6973 0.3348 0.081 Uiso 1 1 calc R . . H4A2 H 0.6196 0.6780 0.2900 0.081 Uiso 1 1 calc R . . H4A3 H 0.6637 0.5934 0.3022 0.081 Uiso 1 1 calc R . . C5A C 0.66089(11) 0.2412(4) 0.42588(13) 0.0351(9) Uani 1 1 d . . . H5AA H 0.6833 0.2954 0.4130 0.042 Uiso 1 1 calc R . . H5AB H 0.6749 0.2119 0.4536 0.042 Uiso 1 1 calc R . . C6A C 0.65124(13) 0.1244(4) 0.39833(14) 0.0437(10) Uani 1 1 d . . . H6AA H 0.6328 0.1503 0.3723 0.052 Uiso 1 1 calc R . . H6AB H 0.6337 0.0613 0.4134 0.052 Uiso 1 1 calc R . . C7A C 0.69443(15) 0.0614(5) 0.38672(17) 0.0605(13) Uani 1 1 d . . . H7AA H 0.7102 0.1210 0.3688 0.073 Uiso 1 1 calc R . . H7AB H 0.7145 0.0452 0.4127 0.073 Uiso 1 1 calc R . . C8A C 0.6855(2) -0.0641(6) 0.3635(2) 0.096(2) Uani 1 1 d . . . H8A1 H 0.6695 -0.1230 0.3810 0.145 Uiso 1 1 calc R . . H8A2 H 0.7141 -0.1030 0.3575 0.145 Uiso 1 1 calc R . . H8A3 H 0.6669 -0.0478 0.3370 0.145 Uiso 1 1 calc R . . C9A C 0.58250(12) 0.2445(4) 0.44900(13) 0.0394(10) Uani 1 1 d . . . H9AA H 0.5571 0.3030 0.4534 0.047 Uiso 1 1 calc R . . H9AB H 0.5718 0.1822 0.4268 0.047 Uiso 1 1 calc R . . C10A C 0.59477(13) 0.1713(4) 0.48931(13) 0.0419(10) Uani 1 1 d . . . H10A H 0.5983 0.2321 0.5133 0.050 Uiso 1 1 calc R . . H10B H 0.6238 0.1262 0.4876 0.050 Uiso 1 1 calc R . . C11A C 0.55819(13) 0.0740(4) 0.49631(13) 0.0461(11) Uani 1 1 d . . . H11B H 0.5529 0.0189 0.4710 0.055 Uiso 1 1 calc R . . H11C H 0.5298 0.1205 0.5000 0.055 Uiso 1 1 calc R . . C12A C 0.57013(15) -0.0108(5) 0.53457(15) 0.0560(12) Uani 1 1 d . . . H12A H 0.5983 -0.0569 0.5312 0.084 Uiso 1 1 calc R . . H12B H 0.5459 -0.0731 0.5373 0.084 Uiso 1 1 calc R . . H12C H 0.5740 0.0429 0.5600 0.084 Uiso 1 1 calc R . . C13A C 0.63605(13) 0.4265(4) 0.46474(13) 0.0404(10) Uani 1 1 d D A . H13A H 0.6473 0.3840 0.4915 0.048 Uiso 1 1 calc R . . H13B H 0.6616 0.4737 0.4542 0.048 Uiso 1 1 calc R . . C14A C 0.60022(16) 0.5223(4) 0.47373(16) 0.0596(13) Uani 1 1 d DU . . H14C H 0.5915 0.5718 0.4488 0.071 Uiso 0.22 1 d PR A . H14D H 0.5742 0.4771 0.4817 0.071 Uiso 0.22 1 d PR . . H14A H 0.5800 0.4809 0.4913 0.071 Uiso 0.78 1 d PR . . H14B H 0.5833 0.5431 0.4475 0.071 Uiso 0.78 1 d PR . . C15A C 0.6152(2) 0.6431(6) 0.4939(2) 0.069(2) Uani 0.78 1 d PDU A 1 H15A H 0.5888 0.6975 0.4985 0.083 Uiso 0.78 1 calc PR A 1 H15B H 0.6344 0.6909 0.4755 0.083 Uiso 0.78 1 calc PR A 1 C16A C 0.6411(2) 0.6144(6) 0.53513(19) 0.0634(17) Uani 0.78 1 d PDU A 1 H16A H 0.6241 0.5536 0.5511 0.095 Uiso 0.78 1 calc PR A 1 H16B H 0.6461 0.6944 0.5513 0.095 Uiso 0.78 1 calc PR A 1 H16C H 0.6703 0.5765 0.5301 0.095 Uiso 0.78 1 calc PR A 1 C15B C 0.6187(6) 0.6136(19) 0.5096(7) 0.076(5) Uiso 0.22 1 d PDU A 2 H15C H 0.5964 0.6828 0.5127 0.092 Uiso 0.22 1 calc PR A 2 H15D H 0.6221 0.5645 0.5364 0.092 Uiso 0.22 1 calc PR A 2 C16B C 0.6634(6) 0.675(2) 0.5028(8) 0.085(6) Uiso 0.22 1 d PDU A 2 H16D H 0.6810 0.6152 0.4869 0.128 Uiso 0.22 1 calc PR A 2 H16E H 0.6799 0.6936 0.5301 0.128 Uiso 0.22 1 calc PR A 2 H16F H 0.6582 0.7548 0.4868 0.128 Uiso 0.22 1 calc PR A 2 Cl1A Cl 0.80006(9) -0.1013(2) 0.50534(10) 0.1661(11) Uani 1 1 d U B -1 C1AA C 0.7475(16) -0.0215(12) 0.5055(12) 0.100(6) Uani 0.50 1 d PU B -1 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 Cl1B 0.0584(7) 0.0634(8) 0.0642(8) -0.0006(6) 0.0330(6) 0.0063(6) Cl2B 0.0566(7) 0.0721(8) 0.0460(7) 0.0083(6) 0.0016(5) 0.0136(6) O1 0.0538(16) 0.0262(14) 0.0223(14) -0.0002(10) -0.0023(12) 0.0005(13) O2 0.0497(17) 0.0496(18) 0.0261(15) -0.0021(12) 0.0058(12) -0.0103(14) N1 0.0302(15) 0.0242(16) 0.0226(16) 0.0037(12) 0.0065(12) 0.0010(12) N2 0.0261(14) 0.0273(16) 0.0235(16) -0.0042(13) 0.0031(12) 0.0014(12) C1 0.0305(17) 0.0131(16) 0.0238(18) 0.0002(14) -0.0023(14) 0.0023(14) C2 0.038(2) 0.029(2) 0.026(2) 0.0070(16) 0.0031(16) 0.0021(16) C3 0.039(2) 0.028(2) 0.027(2) 0.0029(16) 0.0046(16) -0.0029(16) C4 0.0296(18) 0.0184(18) 0.028(2) 0.0001(15) 0.0064(15) -0.0006(15) C5 0.0279(17) 0.0212(18) 0.031(2) 0.0014(15) 0.0045(15) -0.0011(15) C6 0.0208(16) 0.0212(18) 0.031(2) 0.0014(15) 0.0035(14) 0.0005(14) C7 0.0219(16) 0.0232(19) 0.0254(19) -0.0005(15) 0.0013(14) -0.0005(14) C8 0.0182(15) 0.0210(18) 0.0257(19) 0.0001(14) 0.0017(13) 0.0034(14) C9 0.0265(17) 0.0224(18) 0.0271(19) 0.0032(15) 0.0015(14) 0.0005(15) C10 0.0306(18) 0.0254(19) 0.0238(19) -0.0005(15) -0.0006(14) 0.0038(15) C11 0.0297(17) 0.0181(18) 0.029(2) -0.0028(15) 0.0013(15) 0.0001(15) C12 0.0248(16) 0.0184(18) 0.030(2) -0.0013(14) -0.0001(14) 0.0014(14) C13 0.0259(16) 0.0151(17) 0.0256(19) -0.0012(14) 0.0033(14) -0.0003(14) C14 0.0338(18) 0.0239(19) 0.029(2) -0.0074(15) 0.0019(15) -0.0003(16) C15 0.0310(18) 0.031(2) 0.028(2) -0.0044(16) -0.0039(15) -0.0001(16) C16 0.0235(17) 0.0214(18) 0.029(2) 0.0001(15) -0.0024(14) -0.0013(14) C17 0.0229(16) 0.0231(19) 0.040(2) 0.0010(16) 0.0030(15) -0.0025(15) C18 0.0207(16) 0.0237(19) 0.036(2) 0.0013(16) 0.0024(15) 0.0037(14) C19 0.0270(17) 0.0251(19) 0.0258(19) -0.0029(15) 0.0034(14) 0.0037(15) C20 0.0209(16) 0.0245(19) 0.031(2) 0.0028(15) 0.0016(14) 0.0041(14) C21 0.0269(17) 0.027(2) 0.031(2) -0.0053(16) 0.0017(15) 0.0040(15) C22 0.0254(17) 0.035(2) 0.028(2) -0.0029(16) 0.0029(15) 0.0049(16) C23 0.0227(16) 0.029(2) 0.036(2) 0.0072(17) 0.0046(15) 0.0031(15) C24 0.0270(17) 0.0220(19) 0.031(2) 0.0007(15) -0.0011(15) 0.0026(15) C25 0.0324(19) 0.026(2) 0.046(2) 0.0012(18) -0.0022(17) -0.0083(16) C26 0.038(2) 0.033(2) 0.054(3) 0.0062(19) 0.0220(19) 0.0024(18) C27 0.0293(18) 0.033(2) 0.040(2) -0.0123(17) 0.0031(16) 0.0029(17) C28 0.038(2) 0.0207(19) 0.037(2) -0.0009(16) -0.0060(16) 0.0029(16) C29 0.033(2) 0.029(2) 0.053(3) 0.0009(18) 0.0078(18) -0.0016(17) C30 0.0266(18) 0.031(2) 0.056(3) 0.0001(19) -0.0044(17) 0.0041(16) C31 0.036(2) 0.030(2) 0.041(2) 0.0061(17) -0.0050(17) 0.0019(17) C32 0.037(2) 0.024(2) 0.044(2) -0.0004(17) 0.0055(17) 0.0021(16) C1B 0.044(2) 0.035(2) 0.036(2) -0.0032(18) 0.0104(18) 0.0025(18) F1 0.062(2) 0.048(2) 0.049(2) 0.000 0.0257(17) 0.000 O1W 0.083(5) 0.093(6) 0.099(7) -0.006(5) 0.026(5) -0.004(4) N1AA 0.0261(15) 0.0410(19) 0.040(2) 0.0013(15) 0.0017(14) -0.0022(14) C1A 0.032(2) 0.059(3) 0.049(3) 0.007(2) 0.0008(19) 0.003(2) C2A 0.040(2) 0.069(3) 0.047(3) 0.015(2) 0.005(2) 0.001(2) C3A 0.052(3) 0.045(3) 0.062(3) 0.010(2) 0.004(2) 0.014(2) C4A 0.059(3) 0.058(3) 0.046(3) 0.007(2) 0.008(2) 0.013(2) C5A 0.0226(17) 0.042(2) 0.041(2) -0.0006(18) 0.0039(16) -0.0006(16) C6A 0.035(2) 0.052(3) 0.044(3) -0.004(2) 0.0026(18) -0.0046(19) C7A 0.048(3) 0.055(3) 0.081(4) -0.018(3) 0.016(2) 0.005(2) C8A 0.094(4) 0.072(4) 0.129(6) -0.038(4) 0.043(4) -0.008(3) C9A 0.0276(19) 0.043(2) 0.048(3) -0.004(2) 0.0070(17) -0.0037(17) C10A 0.034(2) 0.048(3) 0.043(3) -0.002(2) 0.0058(18) -0.0074(19) C11A 0.040(2) 0.057(3) 0.041(3) -0.002(2) 0.0054(19) -0.010(2) C12A 0.050(3) 0.070(3) 0.047(3) 0.004(2) 0.002(2) -0.011(2) C13A 0.038(2) 0.042(2) 0.044(2) -0.0050(19) 0.0115(18) -0.0076(19) C14A 0.071(3) 0.040(3) 0.070(3) 0.000(2) 0.020(3) 0.001(2) C15A 0.074(4) 0.071(4) 0.064(4) -0.002(3) 0.015(3) -0.001(3) C16A 0.062(3) 0.060(4) 0.070(4) 0.000(3) 0.015(3) 0.006(3) Cl1A 0.159(2) 0.1239(18) 0.221(3) 0.0256(18) 0.052(2) 0.0498(16) C1AA 0.076(8) 0.123(7) 0.100(12) 0.008(8) -0.003(9) -0.008(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 Cl1B C1B 1.746(4) . ? Cl2B C1B 1.767(4) . ? O1 C10 1.335(4) . ? O1 H1O 0.8400 . ? O2 C22 1.360(4) . ? O2 H2O 0.8400 . ? N1 C4 1.369(4) . ? N1 C1 1.383(4) . ? N1 H1N 0.8800 . ? N2 C16 1.374(4) . ? N2 C13 1.375(4) . ? N2 H2N 0.8800 . ? C1 C2 1.346(5) . ? C1 C24 1.524(5) . ? C2 C3 1.420(5) . ? C2 H2 0.9500 . ? C3 C4 1.361(5) . ? C3 H3 0.9500 . ? C4 C5 1.515(5) . ? C5 C26 1.543(5) . ? C5 C6 1.545(5) . ? C5 C25 1.546(5) . ? C6 C11 1.386(5) . ? C6 C7 1.398(5) . ? C7 C8 1.396(5) . ? C7 H7 0.9500 . ? C8 C9 1.386(5) . ? C8 C12 1.545(5) . ? C9 C10 1.398(5) . ? C9 H9 0.9500 . ? C10 C11 1.409(5) . ? C11 H11 0.9500 . ? C12 C13 1.508(5) . ? C12 C28 1.540(5) . ? C12 C27 1.544(5) . ? C13 C14 1.361(5) . ? C14 C15 1.423(5) . ? C14 H14 0.9500 . ? C15 C16 1.347(5) . ? C15 H15 0.9500 . ? C16 C17 1.523(5) . ? C17 C30 1.536(5) . ? C17 C18 1.538(5) . ? C17 C29 1.548(5) . ? C18 C19 1.400(5) . ? C18 C23 1.400(5) . ? C19 C20 1.409(5) . ? C19 H19 0.9500 . ? C20 C21 1.378(5) . ? C20 C24 1.527(5) . ? C21 C22 1.389(5) . ? C21 H21 0.9500 . ? C22 C23 1.386(5) . ? C23 H23 0.9500 . ? C24 C32 1.538(5) . ? C24 C31 1.538(5) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C1B H1BA 0.9900 . ? C1B H1BB 0.9900 . ? N1AA C13A 1.509(5) . ? N1AA C5A 1.514(4) . ? N1AA C1A 1.519(5) . ? N1AA C9A 1.527(5) . ? C1A C2A 1.498(6) . ? C1A H1AA 0.9900 . ? C1A H1AB 0.9900 . ? C2A C3A 1.500(6) . ? C2A H2AA 0.9900 . ? C2A H2AB 0.9900 . ? C3A C4A 1.512(6) . ? C3A H3AA 0.9900 . ? C3A H3AB 0.9900 . ? C4A H4A1 0.9800 . ? C4A H4A2 0.9800 . ? C4A H4A3 0.9800 . ? C5A C6A 1.509(5) . ? C5A H5AA 0.9900 . ? C5A H5AB 0.9900 . ? C6A C7A 1.519(6) . ? C6A H6AA 0.9900 . ? C6A H6AB 0.9900 . ? C7A C8A 1.509(7) . ? C7A H7AA 0.9900 . ? C7A H7AB 0.9900 . ? C8A H8A1 0.9800 . ? C8A H8A2 0.9800 . ? C8A H8A3 0.9800 . ? C9A C10A 1.508(6) . ? C9A H9AA 0.9900 . ? C9A H9AB 0.9900 . ? C10A C11A 1.517(5) . ? C10A H10A 0.9900 . ? C10A H10B 0.9900 . ? C11A C12A 1.519(6) . ? C11A H11B 0.9900 . ? C11A H11C 0.9900 . ? C12A H12A 0.9800 . ? C12A H12B 0.9800 . ? C12A H12C 0.9800 . ? C13A C14A 1.506(6) . ? C13A H13A 0.9900 . ? C13A H13B 0.9900 . ? C14A C15A 1.460(6) . ? C14A C15B 1.547(9) . ? C14A H14C 0.9599 . ? C14A H14D 0.9602 . ? C14A H14A 0.9600 . ? C14A H14B 0.9600 . ? C15A C16A 1.491(7) . ? C15A H15A 0.9900 . ? C15A H15B 0.9900 . ? C16A H16A 0.9800 . ? C16A H16B 0.9800 . ? C16A H16C 0.9800 . ? C15B C16B 1.508(10) . ? C15B H15C 0.9900 . ? C15B H15D 0.9900 . ? C16B H16D 0.9800 . ? C16B H16E 0.9800 . ? C16B H16F 0.9800 . ? Cl1A C1AA 1.77(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 C10 O1 H1O 109.5 . . ? C22 O2 H2O 109.5 . . ? C4 N1 C1 110.5(3) . . ? C4 N1 H1N 124.7 . . ? C1 N1 H1N 124.7 . . ? C16 N2 C13 110.7(3) . . ? C16 N2 H2N 124.7 . . ? C13 N2 H2N 124.7 . . ? C2 C1 N1 106.7(3) . . ? C2 C1 C24 131.4(3) . . ? N1 C1 C24 121.7(3) . . ? C1 C2 C3 108.3(3) . . ? C1 C2 H2 125.8 . . ? C3 C2 H2 125.8 . . ? C4 C3 C2 107.9(3) . . ? C4 C3 H3 126.1 . . ? C2 C3 H3 126.1 . . ? C3 C4 N1 106.6(3) . . ? C3 C4 C5 131.2(3) . . ? N1 C4 C5 121.7(3) . . ? C4 C5 C26 109.3(3) . . ? C4 C5 C6 110.0(3) . . ? C26 C5 C6 109.8(3) . . ? C4 C5 C25 108.2(3) . . ? C26 C5 C25 107.2(3) . . ? C6 C5 C25 112.2(3) . . ? C11 C6 C7 118.9(3) . . ? C11 C6 C5 122.1(3) . . ? C7 C6 C5 118.9(3) . . ? C8 C7 C6 121.1(3) . . ? C8 C7 H7 119.4 . . ? C6 C7 H7 119.4 . . ? C9 C8 C7 118.9(3) . . ? C9 C8 C12 121.9(3) . . ? C7 C8 C12 119.2(3) . . ? C8 C9 C10 121.5(3) . . ? C8 C9 H9 119.2 . . ? C10 C9 H9 119.2 . . ? O1 C10 C9 122.4(3) . . ? O1 C10 C11 119.4(3) . . ? C9 C10 C11 118.2(3) . . ? C6 C11 C10 121.2(3) . . ? C6 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C13 C12 C28 108.5(3) . . ? C13 C12 C27 109.2(3) . . ? C28 C12 C27 107.5(3) . . ? C13 C12 C8 110.3(3) . . ? C28 C12 C8 112.3(3) . . ? C27 C12 C8 109.0(3) . . ? C14 C13 N2 106.3(3) . . ? C14 C13 C12 132.1(3) . . ? N2 C13 C12 121.4(3) . . ? C13 C14 C15 107.9(3) . . ? C13 C14 H14 126.0 . . ? C15 C14 H14 126.0 . . ? C16 C15 C14 108.1(3) . . ? C16 C15 H15 125.9 . . ? C14 C15 H15 125.9 . . ? C15 C16 N2 106.9(3) . . ? C15 C16 C17 132.0(3) . . ? N2 C16 C17 120.9(3) . . ? C16 C17 C30 109.2(3) . . ? C16 C17 C18 110.2(3) . . ? C30 C17 C18 109.1(3) . . ? C16 C17 C29 107.9(3) . . ? C30 C17 C29 108.0(3) . . ? C18 C17 C29 112.5(3) . . ? C19 C18 C23 118.6(3) . . ? C19 C18 C17 119.3(3) . . ? C23 C18 C17 122.1(3) . . ? C18 C19 C20 121.6(3) . . ? C18 C19 H19 119.2 . . ? C20 C19 H19 119.2 . . ? C21 C20 C19 118.2(3) . . ? C21 C20 C24 122.5(3) . . ? C19 C20 C24 119.2(3) . . ? C20 C21 C22 121.0(3) . . ? C20 C21 H21 119.5 . . ? C22 C21 H21 119.5 . . ? O2 C22 C23 121.5(3) . . ? O2 C22 C21 117.7(3) . . ? C23 C22 C21 120.8(3) . . ? C22 C23 C18 119.8(3) . . ? C22 C23 H23 120.1 . . ? C18 C23 H23 120.1 . . ? C1 C24 C20 111.0(3) . . ? C1 C24 C32 107.7(3) . . ? C20 C24 C32 112.1(3) . . ? C1 C24 C31 108.9(3) . . ? C20 C24 C31 109.6(3) . . ? C32 C24 C31 107.4(3) . . ? C5 C25 H25A 109.5 . . ? C5 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C5 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C5 C26 H26A 109.5 . . ? C5 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C5 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C12 C27 H27A 109.5 . . ? C12 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C12 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C12 C28 H28A 109.5 . . ? C12 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C12 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C17 C29 H29A 109.5 . . ? C17 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C17 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C17 C30 H30A 109.5 . . ? C17 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C17 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C24 C31 H31A 109.5 . . ? C24 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C24 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C24 C32 H32A 109.5 . . ? C24 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C24 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? Cl1B C1B Cl2B 111.8(2) . . ? Cl1B C1B H1BA 109.3 . . ? Cl2B C1B H1BA 109.3 . . ? Cl1B C1B H1BB 109.3 . . ? Cl2B C1B H1BB 109.3 . . ? H1BA C1B H1BB 107.9 . . ? C13A N1AA C5A 107.6(3) . . ? C13A N1AA C1A 111.2(3) . . ? C5A N1AA C1A 109.8(3) . . ? C13A N1AA C9A 110.5(3) . . ? C5A N1AA C9A 111.5(3) . . ? C1A N1AA C9A 106.3(3) . . ? C2A C1A N1AA 116.0(3) . . ? C2A C1A H1AA 108.3 . . ? N1AA C1A H1AA 108.3 . . ? C2A C1A H1AB 108.3 . . ? N1AA C1A H1AB 108.3 . . ? H1AA C1A H1AB 107.4 . . ? C1A C2A C3A 111.5(4) . . ? C1A C2A H2AA 109.3 . . ? C3A C2A H2AA 109.3 . . ? C1A C2A H2AB 109.3 . . ? C3A C2A H2AB 109.3 . . ? H2AA C2A H2AB 108.0 . . ? C2A C3A C4A 112.6(4) . . ? C2A C3A H3AA 109.1 . . ? C4A C3A H3AA 109.1 . . ? C2A C3A H3AB 109.1 . . ? C4A C3A H3AB 109.1 . . ? H3AA C3A H3AB 107.8 . . ? C3A C4A H4A1 109.5 . . ? C3A C4A H4A2 109.5 . . ? H4A1 C4A H4A2 109.5 . . ? C3A C4A H4A3 109.5 . . ? H4A1 C4A H4A3 109.5 . . ? H4A2 C4A H4A3 109.5 . . ? C6A C5A N1AA 115.7(3) . . ? C6A C5A H5AA 108.4 . . ? N1AA C5A H5AA 108.4 . . ? C6A C5A H5AB 108.4 . . ? N1AA C5A H5AB 108.4 . . ? H5AA C5A H5AB 107.4 . . ? C5A C6A C7A 111.5(3) . . ? C5A C6A H6AA 109.3 . . ? C7A C6A H6AA 109.3 . . ? C5A C6A H6AB 109.3 . . ? C7A C6A H6AB 109.3 . . ? H6AA C6A H6AB 108.0 . . ? C8A C7A C6A 112.0(4) . . ? C8A C7A H7AA 109.2 . . ? C6A C7A H7AA 109.2 . . ? C8A C7A H7AB 109.2 . . ? C6A C7A H7AB 109.2 . . ? H7AA C7A H7AB 107.9 . . ? C7A C8A H8A1 109.5 . . ? C7A C8A H8A2 109.5 . . ? H8A1 C8A H8A2 109.5 . . ? C7A C8A H8A3 109.5 . . ? H8A1 C8A H8A3 109.5 . . ? H8A2 C8A H8A3 109.5 . . ? C10A C9A N1AA 115.3(3) . . ? C10A C9A H9AA 108.5 . . ? N1AA C9A H9AA 108.5 . . ? C10A C9A H9AB 108.5 . . ? N1AA C9A H9AB 108.5 . . ? H9AA C9A H9AB 107.5 . . ? C9A C10A C11A 109.9(3) . . ? C9A C10A H10A 109.7 . . ? C11A C10A H10A 109.7 . . ? C9A C10A H10B 109.7 . . ? C11A C10A H10B 109.7 . . ? H10A C10A H10B 108.2 . . ? C10A C11A C12A 112.7(3) . . ? C10A C11A H11B 109.1 . . ? C12A C11A H11B 109.1 . . ? C10A C11A H11C 109.1 . . ? C12A C11A H11C 109.1 . . ? H11B C11A H11C 107.8 . . ? C11A C12A H12A 109.5 . . ? C11A C12A H12B 109.5 . . ? H12A C12A H12B 109.5 . . ? C11A C12A H12C 109.5 . . ? H12A C12A H12C 109.5 . . ? H12B C12A H12C 109.5 . . ? C14A C13A N1AA 114.4(3) . . ? C14A C13A H13A 108.7 . . ? N1AA C13A H13A 108.7 . . ? C14A C13A H13B 108.7 . . ? N1AA C13A H13B 108.7 . . ? H13A C13A H13B 107.6 . . ? C15A C14A C13A 117.3(4) . . ? C13A C14A C15B 109.6(8) . . ? C13A C14A H14C 109.8 . . ? C15B C14A H14C 109.5 . . ? C13A C14A H14D 109.4 . . ? C15B C14A H14D 110.2 . . ? H14C C14A H14D 108.4 . . ? C15A C14A H14A 108.1 . . ? C13A C14A H14A 108.0 . . ? C15A C14A H14B 107.7 . . ? C13A C14A H14B 107.9 . . ? H14A C14A H14B 107.5 . . ? C14A C15A C16A 109.2(5) . . ? C14A C15A H15A 109.8 . . ? C16A C15A H15A 109.8 . . ? C14A C15A H15B 109.8 . . ? C16A C15A H15B 109.8 . . ? H15A C15A H15B 108.3 . . ? C16B C15B C14A 114.1(9) . . ? C16B C15B H15C 108.7 . . ? C14A C15B H15C 108.7 . . ? C16B C15B H15D 108.7 . . ? C14A C15B H15D 108.7 . . ? H15C C15B H15D 107.6 . . ? C15B C16B H16D 109.5 . . ? C15B C16B H16E 109.5 . . ? H16D C16B H16E 109.5 . . ? C15B C16B H16F 109.5 . . ? H16D C16B H16F 109.5 . . ? H16E C16B H16F 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 C4 N1 C1 C2 0.9(4) . . . . ? C4 N1 C1 C24 175.9(3) . . . . ? N1 C1 C2 C3 -0.3(4) . . . . ? C24 C1 C2 C3 -174.5(3) . . . . ? C1 C2 C3 C4 -0.5(4) . . . . ? C2 C3 C4 N1 1.0(4) . . . . ? C2 C3 C4 C5 173.2(3) . . . . ? C1 N1 C4 C3 -1.2(4) . . . . ? C1 N1 C4 C5 -174.3(3) . . . . ? C3 C4 C5 C26 31.5(5) . . . . ? N1 C4 C5 C26 -157.4(3) . . . . ? C3 C4 C5 C6 152.1(4) . . . . ? N1 C4 C5 C6 -36.7(4) . . . . ? C3 C4 C5 C25 -85.0(5) . . . . ? N1 C4 C5 C25 86.1(4) . . . . ? C4 C5 C6 C11 112.5(3) . . . . ? C26 C5 C6 C11 -127.1(3) . . . . ? C25 C5 C6 C11 -8.0(4) . . . . ? C4 C5 C6 C7 -66.9(4) . . . . ? C26 C5 C6 C7 53.5(4) . . . . ? C25 C5 C6 C7 172.6(3) . . . . ? C11 C6 C7 C8 2.4(5) . . . . ? C5 C6 C7 C8 -178.2(3) . . . . ? C6 C7 C8 C9 -1.8(5) . . . . ? C6 C7 C8 C12 177.8(3) . . . . ? C7 C8 C9 C10 -0.4(5) . . . . ? C12 C8 C9 C10 -180.0(3) . . . . ? C8 C9 C10 O1 -179.2(3) . . . . ? C8 C9 C10 C11 2.0(5) . . . . ? C7 C6 C11 C10 -0.6(5) . . . . ? C5 C6 C11 C10 179.9(3) . . . . ? O1 C10 C11 C6 179.7(3) . . . . ? C9 C10 C11 C6 -1.5(5) . . . . ? C9 C8 C12 C13 -116.9(3) . . . . ? C7 C8 C12 C13 63.6(4) . . . . ? C9 C8 C12 C28 4.3(4) . . . . ? C7 C8 C12 C28 -175.3(3) . . . . ? C9 C8 C12 C27 123.2(3) . . . . ? C7 C8 C12 C27 -56.3(4) . . . . ? C16 N2 C13 C14 0.0(4) . . . . ? C16 N2 C13 C12 176.0(3) . . . . ? C28 C12 C13 C14 97.0(4) . . . . ? C27 C12 C13 C14 -19.9(5) . . . . ? C8 C12 C13 C14 -139.6(4) . . . . ? C28 C12 C13 N2 -77.8(4) . . . . ? C27 C12 C13 N2 165.3(3) . . . . ? C8 C12 C13 N2 45.6(4) . . . . ? N2 C13 C14 C15 0.3(4) . . . . ? C12 C13 C14 C15 -175.1(3) . . . . ? C13 C14 C15 C16 -0.5(4) . . . . ? C14 C15 C16 N2 0.4(4) . . . . ? C14 C15 C16 C17 175.6(3) . . . . ? C13 N2 C16 C15 -0.3(4) . . . . ? C13 N2 C16 C17 -176.0(3) . . . . ? C15 C16 C17 C30 22.6(5) . . . . ? N2 C16 C17 C30 -162.9(3) . . . . ? C15 C16 C17 C18 142.3(4) . . . . ? N2 C16 C17 C18 -43.1(4) . . . . ? C15 C16 C17 C29 -94.5(5) . . . . ? N2 C16 C17 C29 80.0(4) . . . . ? C16 C17 C18 C19 -62.5(4) . . . . ? C30 C17 C18 C19 57.3(4) . . . . ? C29 C17 C18 C19 177.1(3) . . . . ? C16 C17 C18 C23 117.6(3) . . . . ? C30 C17 C18 C23 -122.6(3) . . . . ? C29 C17 C18 C23 -2.8(4) . . . . ? C23 C18 C19 C20 1.1(5) . . . . ? C17 C18 C19 C20 -178.7(3) . . . . ? C18 C19 C20 C21 -2.3(5) . . . . ? C18 C19 C20 C24 174.7(3) . . . . ? C19 C20 C21 C22 1.9(5) . . . . ? C24 C20 C21 C22 -174.9(3) . . . . ? C20 C21 C22 O2 178.8(3) . . . . ? C20 C21 C22 C23 -0.5(5) . . . . ? O2 C22 C23 C18 -179.9(3) . . . . ? C21 C22 C23 C18 -0.7(5) . . . . ? C19 C18 C23 C22 0.3(5) . . . . ? C17 C18 C23 C22 -179.8(3) . . . . ? C2 C1 C24 C20 -148.8(4) . . . . ? N1 C1 C24 C20 37.7(4) . . . . ? C2 C1 C24 C32 88.2(4) . . . . ? N1 C1 C24 C32 -85.4(4) . . . . ? C2 C1 C24 C31 -28.0(5) . . . . ? N1 C1 C24 C31 158.5(3) . . . . ? C21 C20 C24 C1 -117.3(3) . . . . ? C19 C20 C24 C1 65.9(4) . . . . ? C21 C20 C24 C32 3.2(4) . . . . ? C19 C20 C24 C32 -173.6(3) . . . . ? C21 C20 C24 C31 122.3(4) . . . . ? C19 C20 C24 C31 -54.5(4) . . . . ? C13A N1AA C1A C2A 56.0(5) . . . . ? C5A N1AA C1A C2A -62.9(5) . . . . ? C9A N1AA C1A C2A 176.3(4) . . . . ? N1AA C1A C2A C3A -176.5(4) . . . . ? C1A C2A C3A C4A 174.0(4) . . . . ? C13A N1AA C5A C6A 174.0(3) . . . . ? C1A N1AA C5A C6A -64.8(4) . . . . ? C9A N1AA C5A C6A 52.7(4) . . . . ? N1AA C5A C6A C7A 169.9(4) . . . . ? C5A C6A C7A C8A 173.2(5) . . . . ? C13A N1AA C9A C10A -61.9(4) . . . . ? C5A N1AA C9A C10A 57.7(4) . . . . ? C1A N1AA C9A C10A 177.4(3) . . . . ? N1AA C9A C10A C11A -167.2(3) . . . . ? C9A C10A C11A C12A 175.4(4) . . . . ? C5A N1AA C13A C14A 176.9(3) . . . . ? C1A N1AA C13A C14A 56.6(4) . . . . ? C9A N1AA C13A C14A -61.2(4) . . . . ? N1AA C13A C14A C15A -162.7(4) . . . . ? N1AA C13A C14A C15B 174.5(11) . . . . ? C13A C14A C15A C16A -58.8(7) . . . . ? C15B C14A C15A C16A 15.9(16) . . . . ? C15A C14A C15B C16B -63(2) . . . . ? C13A C14A C15B C16B 51(2) . . . . ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.995 _refine_diff_density_min -1.248 _refine_diff_density_rms 0.082