# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_cu_mh116_0m _audit_creation_method SHELXTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C50H53N5O4) (HCl) (HCCl3) (C5H12)' _chemical_formula_sum 'C56 H67 Cl4 N5 O4' _chemical_formula_weight 1015.95 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 14.6699(8) _cell_length_b 13.9019(8) _cell_length_c 27.0087(15) _cell_angle_alpha 90.00 _cell_angle_beta 102.838(3) _cell_angle_gamma 90.00 _cell_volume 5370.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9916 _cell_measurement_theta_min 3.17 _cell_measurement_theta_max 67.83 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.257 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2152 _exptl_absorpt_coefficient_mu 2.392 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6592 _exptl_absorpt_correction_T_max 0.9537 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus Icotec I\MS tube' _diffrn_radiation_monochromator optics _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 37694 _diffrn_reflns_av_R_equivalents 0.0531 _diffrn_reflns_av_sigmaI/netI 0.0500 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.17 _diffrn_reflns_theta_max 67.83 _reflns_number_total 9580 _reflns_number_gt 7599 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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. In the crystal structure there is pentane, CH3CH2CH2CH2CH3, solvent molecule disordered over two positions related by an inversion center. It was treated by SQUEEZE [Van der Sluis,P. & Spek, A.L. (1990) Acta Cryst., Sect.A,A46,194-201.]. Corrections of the X-ray data by SQUEEZE (193 electron/cell) was close to the required values (168 electron/cell). ; _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^)+(0.1806P)^2^+6.0085P] 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 9580 _refine_ls_number_parameters 577 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1023 _refine_ls_R_factor_gt 0.0891 _refine_ls_wR_factor_ref 0.2771 _refine_ls_wR_factor_gt 0.2627 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 0.002 _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 Cl1 Cl 0.68866(6) 0.54324(6) 0.03730(3) 0.0319(2) Uani 1 1 d . . . O1 O 0.98735(18) 0.74637(19) 0.06721(10) 0.0359(6) Uani 1 1 d . . . O2 O 0.8309(2) 0.8598(2) 0.26816(10) 0.0444(7) Uani 1 1 d . . . O3 O 0.5572(2) 1.05712(19) 0.09239(12) 0.0444(7) Uani 1 1 d . . . O4 O 0.39377(18) 0.62688(18) 0.10149(10) 0.0362(6) Uani 1 1 d . . . N1 N 0.7284(2) 0.3437(2) 0.00270(11) 0.0262(6) Uani 1 1 d . . . H1A H 0.7208 0.4027 0.0129 0.031 Uiso 1 1 calc R . . N2 N 0.8922(2) 0.6440(2) 0.01206(12) 0.0309(7) Uani 1 1 d . . . H2A H 0.8416 0.6083 0.0082 0.037 Uiso 1 1 calc R . . N3 N 0.8599(2) 0.6781(2) 0.08873(12) 0.0349(7) Uani 1 1 d . . . H3A H 0.8178 0.6324 0.0800 0.042 Uiso 1 1 calc R . . N4 N 0.5237(2) 0.6583(2) 0.07079(11) 0.0305(7) Uani 1 1 d . . . H4A H 0.5669 0.6315 0.0574 0.037 Uiso 1 1 calc R . . N5 N 0.4785(2) 0.5029(2) 0.07768(11) 0.0280(6) Uani 1 1 d . . . H5A H 0.5268 0.4903 0.0644 0.034 Uiso 1 1 calc R . . C1 C 0.6754(2) 0.2735(3) 0.01578(13) 0.0279(7) Uani 1 1 d . . . C2 C 0.6870(3) 0.1799(3) 0.00040(15) 0.0345(8) Uani 1 1 d . . . H2B H 0.6502 0.1290 0.0091 0.041 Uiso 1 1 calc R . . C3 C 0.7533(3) 0.1620(3) -0.02793(16) 0.0368(8) Uani 1 1 d . . . H3B H 0.7620 0.0981 -0.0385 0.044 Uiso 1 1 calc R . . C4 C 0.8066(3) 0.2350(3) -0.04091(14) 0.0323(8) Uani 1 1 d . . . H4B H 0.8522 0.2220 -0.0601 0.039 Uiso 1 1 calc R . . C5 C 0.7926(2) 0.3285(3) -0.02534(13) 0.0277(7) Uani 1 1 d . . . C6 C 0.8419(2) 0.4095(3) -0.03730(13) 0.0288(7) Uani 1 1 d . . . C7 C 0.8835(2) 0.4783(3) -0.04753(13) 0.0288(7) Uani 1 1 d . . . C8 C 0.9330(2) 0.5612(2) -0.05859(13) 0.0277(7) Uani 1 1 d . . . C9 C 0.9759(3) 0.5583(3) -0.09995(14) 0.0311(8) Uani 1 1 d . . . H9A H 0.9718 0.5013 -0.1197 0.037 Uiso 1 1 calc R . . C10 C 1.0247(3) 0.6374(3) -0.11276(14) 0.0337(8) Uani 1 1 d . . . C11 C 1.0280(3) 0.7187(3) -0.08184(15) 0.0349(8) Uani 1 1 d . . . H11A H 1.0607 0.7737 -0.0896 0.042 Uiso 1 1 calc R . . C12 C 0.9866(3) 0.7235(3) -0.04075(14) 0.0319(8) Uani 1 1 d . . . H12A H 0.9914 0.7806 -0.0210 0.038 Uiso 1 1 calc R . . C13 C 0.9379(2) 0.6444(3) -0.02843(13) 0.0291(7) Uani 1 1 d . . . C14 C 1.0692(3) 0.6367(3) -0.15910(15) 0.0389(9) Uani 1 1 d . . . C15 C 1.0548(4) 0.5414(4) -0.18758(19) 0.0539(12) Uani 1 1 d . . . H15A H 1.0846 0.5442 -0.2166 0.081 Uiso 1 1 calc R . . H15B H 0.9877 0.5294 -0.1997 0.081 Uiso 1 1 calc R . . H15C H 1.0828 0.4894 -0.1648 0.081 Uiso 1 1 calc R . . C16 C 1.1745(3) 0.6554(4) -0.14140(17) 0.0482(11) Uani 1 1 d . . . H16A H 1.2035 0.6546 -0.1708 0.072 Uiso 1 1 calc R . . H16B H 1.2027 0.6051 -0.1174 0.072 Uiso 1 1 calc R . . H16C H 1.1847 0.7183 -0.1247 0.072 Uiso 1 1 calc R . . C17 C 1.0242(4) 0.7164(4) -0.19547(17) 0.0548(12) Uani 1 1 d . . . H17A H 1.0519 0.7168 -0.2253 0.082 Uiso 1 1 calc R . . H17B H 1.0350 0.7787 -0.1782 0.082 Uiso 1 1 calc R . . H17C H 0.9568 0.7047 -0.2062 0.082 Uiso 1 1 calc R . . C18 C 0.9182(3) 0.6937(3) 0.05721(14) 0.0299(7) Uani 1 1 d . . . C19 C 0.8599(3) 0.7285(3) 0.13473(13) 0.0307(8) Uani 1 1 d . . . C20 C 0.9393(3) 0.7476(3) 0.17129(16) 0.0407(9) Uani 1 1 d . . . H20A H 0.9987 0.7291 0.1659 0.049 Uiso 1 1 calc R . . C21 C 0.9330(3) 0.7941(3) 0.21623(16) 0.0404(9) Uani 1 1 d . . . H21A H 0.9880 0.8075 0.2414 0.048 Uiso 1 1 calc R . . C22 C 0.8466(3) 0.8203(3) 0.22396(14) 0.0361(8) Uani 1 1 d . . . C23 C 0.7676(3) 0.8026(3) 0.18732(15) 0.0374(8) Uani 1 1 d . . . H23A H 0.7083 0.8216 0.1926 0.045 Uiso 1 1 calc R . . C24 C 0.7737(3) 0.7573(3) 0.14281(15) 0.0362(8) Uani 1 1 d . . . H24A H 0.7186 0.7458 0.1174 0.043 Uiso 1 1 calc R . . C25 C 0.9070(3) 0.9026(3) 0.30401(15) 0.0440(10) Uani 1 1 d . . . H25A H 0.9632 0.8619 0.3070 0.053 Uiso 1 1 calc R . . H25B H 0.8910 0.9048 0.3377 0.053 Uiso 1 1 calc R . . C26 C 0.9292(3) 1.0034(3) 0.28903(15) 0.0411(9) Uani 1 1 d . . . H26A H 0.9313 1.0035 0.2527 0.049 Uiso 1 1 calc R . . H26B H 0.9920 1.0216 0.3088 0.049 Uiso 1 1 calc R . . C27 C 0.8587(3) 1.0795(3) 0.29763(17) 0.0489(10) Uani 1 1 d . . . H27A H 0.8554 1.0775 0.3338 0.059 Uiso 1 1 calc R . . H27B H 0.8829 1.1436 0.2911 0.059 Uiso 1 1 calc R . . C28 C 0.7599(3) 1.0693(3) 0.26522(17) 0.0450(10) Uani 1 1 d . . . H28A H 0.7372 1.0033 0.2693 0.054 Uiso 1 1 calc R . . H28B H 0.7183 1.1146 0.2779 0.054 Uiso 1 1 calc R . . C29 C 0.7527(3) 1.0882(3) 0.20954(17) 0.0474(10) Uani 1 1 d . . . H29A H 0.7972 1.0461 0.1970 0.057 Uiso 1 1 calc R . . H29B H 0.7699 1.1559 0.2047 0.057 Uiso 1 1 calc R . . C30 C 0.6529(3) 1.0690(3) 0.17887(18) 0.0471(10) Uani 1 1 d . . . H30A H 0.6346 1.0023 0.1851 0.057 Uiso 1 1 calc R . . H30B H 0.6090 1.1134 0.1903 0.057 Uiso 1 1 calc R . . C31 C 0.6462(4) 1.0829(3) 0.12309(18) 0.0500(11) Uani 1 1 d . . . H31A H 0.6589 1.1512 0.1168 0.060 Uiso 1 1 calc R . . H31B H 0.6951 1.0436 0.1127 0.060 Uiso 1 1 calc R . . C32 C 0.5469(3) 0.9582(3) 0.08692(17) 0.0397(9) Uani 1 1 d . . . C33 C 0.5808(3) 0.9109(3) 0.04976(15) 0.0379(9) Uani 1 1 d . . . H33A H 0.6111 0.9462 0.0280 0.045 Uiso 1 1 calc R . . C34 C 0.5706(3) 0.8118(3) 0.04411(15) 0.0348(8) Uani 1 1 d . . . H34A H 0.5939 0.7798 0.0184 0.042 Uiso 1 1 calc R . . C35 C 0.5264(3) 0.7590(3) 0.07603(14) 0.0323(8) Uani 1 1 d . . . C36 C 0.4900(3) 0.8069(3) 0.11261(17) 0.0420(9) Uani 1 1 d . . . H36A H 0.4589 0.7720 0.1342 0.050 Uiso 1 1 calc R . . C37 C 0.4995(3) 0.9061(3) 0.11729(18) 0.0461(10) Uani 1 1 d . . . H37A H 0.4733 0.9389 0.1417 0.055 Uiso 1 1 calc R . . C38 C 0.4599(3) 0.5986(3) 0.08469(13) 0.0296(7) Uani 1 1 d . . . C39 C 0.4281(2) 0.4238(3) 0.08956(12) 0.0275(7) Uani 1 1 d . . . C40 C 0.4625(2) 0.3310(3) 0.08300(12) 0.0266(7) Uani 1 1 d . . . C41 C 0.4183(3) 0.2494(3) 0.09700(13) 0.0293(7) Uani 1 1 d . . . H41A H 0.4427 0.1875 0.0924 0.035 Uiso 1 1 calc R . . C42 C 0.3394(3) 0.2565(3) 0.11751(13) 0.0309(8) Uani 1 1 d . . . C43 C 0.3052(3) 0.3483(3) 0.12240(14) 0.0345(8) Uani 1 1 d . . . H43A H 0.2507 0.3551 0.1356 0.041 Uiso 1 1 calc R . . C44 C 0.3476(3) 0.4306(3) 0.10880(14) 0.0335(8) Uani 1 1 d . . . H44A H 0.3215 0.4919 0.1126 0.040 Uiso 1 1 calc R . . C45 C 0.2973(3) 0.1648(3) 0.13475(16) 0.0389(9) Uani 1 1 d . . . C46 C 0.2089(3) 0.1861(3) 0.15427(18) 0.0447(10) Uani 1 1 d . . . H46A H 0.1616 0.2153 0.1270 0.067 Uiso 1 1 calc R . . H46B H 0.2241 0.2306 0.1831 0.067 Uiso 1 1 calc R . . H46C H 0.1844 0.1260 0.1652 0.067 Uiso 1 1 calc R . . C47 C 0.2738(4) 0.0940(4) 0.0908(2) 0.0655(16) Uani 1 1 d . . . H47A H 0.2270 0.1225 0.0630 0.098 Uiso 1 1 calc R . . H47B H 0.2488 0.0347 0.1022 0.098 Uiso 1 1 calc R . . H47C H 0.3305 0.0792 0.0787 0.098 Uiso 1 1 calc R . . C48 C 0.3706(3) 0.1184(3) 0.1777(2) 0.0541(12) Uani 1 1 d . . . H48A H 0.3446 0.0598 0.1892 0.081 Uiso 1 1 calc R . . H48B H 0.3874 0.1637 0.2061 0.081 Uiso 1 1 calc R . . H48C H 0.4264 0.1023 0.1651 0.081 Uiso 1 1 calc R . . C49 C 0.5423(2) 0.3168(2) 0.06198(13) 0.0268(7) Uani 1 1 d . . . C50 C 0.6061(3) 0.2999(2) 0.04272(13) 0.0282(7) Uani 1 1 d . . . C1S C 0.9551(4) 0.9507(3) 0.0932(2) 0.0615(14) Uani 1 1 d . . . H1SA H 0.9715 0.8840 0.1061 0.074 Uiso 1 1 calc R . . Cl1S Cl 0.84673(15) 0.94646(18) 0.04768(11) 0.1223(9) Uani 1 1 d . . . Cl2S Cl 0.9448(3) 1.02272(14) 0.14362(9) 0.1507(14) Uani 1 1 d . . . Cl3S Cl 1.04315(13) 0.99284(11) 0.06534(8) 0.0869(6) Uani 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 Cl1 0.0327(4) 0.0261(4) 0.0407(5) -0.0063(3) 0.0163(4) -0.0011(3) O1 0.0331(13) 0.0333(13) 0.0462(15) -0.0086(11) 0.0193(12) -0.0064(11) O2 0.0486(17) 0.0502(17) 0.0364(14) -0.0112(13) 0.0139(12) -0.0047(14) O3 0.0494(17) 0.0233(13) 0.0529(17) -0.0006(12) -0.0048(13) 0.0048(12) O4 0.0361(14) 0.0278(13) 0.0488(15) 0.0026(11) 0.0178(12) 0.0073(11) N1 0.0292(14) 0.0214(13) 0.0303(14) -0.0033(11) 0.0118(12) 0.0011(11) N2 0.0306(15) 0.0289(15) 0.0372(16) -0.0063(13) 0.0161(13) -0.0048(12) N3 0.0361(16) 0.0380(17) 0.0349(16) -0.0106(14) 0.0174(13) -0.0107(14) N4 0.0368(16) 0.0207(14) 0.0377(16) 0.0037(12) 0.0159(13) 0.0068(12) N5 0.0279(14) 0.0258(15) 0.0329(14) 0.0023(12) 0.0122(12) 0.0031(12) C1 0.0278(17) 0.0258(17) 0.0330(17) -0.0022(14) 0.0133(14) -0.0018(14) C2 0.0334(19) 0.0265(18) 0.049(2) -0.0044(16) 0.0197(17) -0.0068(15) C3 0.0359(19) 0.0244(17) 0.053(2) -0.0098(16) 0.0166(17) -0.0007(15) C4 0.0297(18) 0.0308(18) 0.0398(19) -0.0052(15) 0.0150(15) 0.0013(15) C5 0.0276(17) 0.0280(17) 0.0291(16) -0.0015(14) 0.0101(14) -0.0004(14) C6 0.0310(17) 0.0286(18) 0.0315(17) -0.0045(14) 0.0169(14) 0.0015(15) C7 0.0298(17) 0.0275(17) 0.0311(17) -0.0029(14) 0.0112(14) 0.0044(15) C8 0.0267(16) 0.0263(17) 0.0326(17) -0.0005(14) 0.0121(14) 0.0013(14) C9 0.0320(18) 0.0274(17) 0.0359(18) -0.0013(15) 0.0118(15) 0.0001(14) C10 0.0323(18) 0.038(2) 0.0335(18) 0.0047(16) 0.0128(15) 0.0000(16) C11 0.038(2) 0.0259(18) 0.043(2) 0.0057(16) 0.0129(16) -0.0020(15) C12 0.0346(19) 0.0269(17) 0.0359(18) -0.0020(15) 0.0115(15) -0.0009(15) C13 0.0294(17) 0.0301(18) 0.0286(16) 0.0020(14) 0.0080(14) 0.0016(14) C14 0.039(2) 0.042(2) 0.041(2) 0.0030(17) 0.0193(17) -0.0016(17) C15 0.060(3) 0.060(3) 0.053(3) -0.006(2) 0.038(2) -0.005(2) C16 0.045(2) 0.064(3) 0.042(2) 0.007(2) 0.0247(19) -0.003(2) C17 0.062(3) 0.067(3) 0.041(2) 0.016(2) 0.024(2) 0.012(2) C18 0.0303(18) 0.0260(17) 0.0357(18) -0.0050(15) 0.0125(15) 0.0024(14) C19 0.040(2) 0.0256(17) 0.0292(17) -0.0006(14) 0.0134(15) -0.0048(15) C20 0.038(2) 0.045(2) 0.044(2) -0.0062(18) 0.0172(17) -0.0027(17) C21 0.039(2) 0.041(2) 0.040(2) -0.0054(17) 0.0053(17) -0.0024(17) C22 0.043(2) 0.0338(19) 0.0339(18) -0.0012(16) 0.0136(16) -0.0038(16) C23 0.036(2) 0.040(2) 0.040(2) -0.0021(17) 0.0159(16) -0.0017(16) C24 0.0345(19) 0.041(2) 0.0345(19) -0.0003(16) 0.0109(15) -0.0007(16) C25 0.052(2) 0.048(2) 0.0301(18) -0.0081(18) 0.0050(17) -0.004(2) C26 0.042(2) 0.049(2) 0.0320(18) -0.0023(17) 0.0071(16) -0.0045(18) C27 0.059(3) 0.046(2) 0.040(2) -0.0074(19) 0.007(2) 0.000(2) C28 0.046(2) 0.036(2) 0.054(2) -0.0026(19) 0.013(2) 0.0014(18) C29 0.046(2) 0.047(2) 0.048(2) -0.001(2) 0.0087(19) -0.001(2) C30 0.046(2) 0.039(2) 0.056(3) -0.002(2) 0.012(2) -0.0014(19) C31 0.059(3) 0.036(2) 0.052(2) 0.0014(19) 0.006(2) -0.007(2) C32 0.038(2) 0.0242(18) 0.053(2) 0.0039(17) 0.0018(18) 0.0041(15) C33 0.042(2) 0.0296(19) 0.0390(19) 0.0048(16) 0.0027(17) -0.0022(16) C34 0.039(2) 0.0282(18) 0.0381(19) 0.0036(15) 0.0094(16) 0.0010(15) C35 0.0315(18) 0.0250(17) 0.0388(19) 0.0040(15) 0.0044(15) 0.0048(14) C36 0.045(2) 0.0298(19) 0.056(2) -0.0014(18) 0.022(2) 0.0030(17) C37 0.046(2) 0.034(2) 0.062(3) -0.0074(19) 0.019(2) 0.0077(18) C38 0.0316(18) 0.0292(18) 0.0292(16) 0.0036(14) 0.0090(14) 0.0047(14) C39 0.0286(17) 0.0284(17) 0.0261(16) 0.0020(14) 0.0073(13) 0.0024(14) C40 0.0267(17) 0.0290(17) 0.0247(15) -0.0005(13) 0.0067(13) -0.0005(14) C41 0.0317(18) 0.0271(17) 0.0313(17) -0.0015(14) 0.0116(14) 0.0008(14) C42 0.0311(18) 0.0329(19) 0.0316(17) -0.0022(15) 0.0130(14) -0.0051(15) C43 0.0301(18) 0.038(2) 0.0398(19) 0.0003(16) 0.0175(15) 0.0004(15) C44 0.0287(18) 0.0331(19) 0.0407(19) 0.0028(16) 0.0122(15) 0.0064(15) C45 0.040(2) 0.035(2) 0.048(2) -0.0052(17) 0.0242(18) -0.0089(17) C46 0.039(2) 0.045(2) 0.057(2) 0.002(2) 0.0245(19) -0.0046(18) C47 0.073(3) 0.064(3) 0.073(3) -0.029(3) 0.045(3) -0.040(3) C48 0.051(3) 0.044(2) 0.075(3) 0.023(2) 0.028(2) 0.003(2) C49 0.0308(17) 0.0216(16) 0.0289(16) 0.0007(13) 0.0088(14) -0.0013(13) C50 0.0322(18) 0.0219(16) 0.0330(17) 0.0018(14) 0.0126(15) -0.0033(14) C1S 0.087(4) 0.034(2) 0.075(3) -0.005(2) 0.043(3) -0.003(2) Cl1S 0.0817(12) 0.1115(16) 0.158(2) 0.0503(15) -0.0064(13) 0.0119(11) Cl2S 0.319(4) 0.0595(10) 0.1112(16) -0.0200(10) 0.129(2) -0.0147(16) Cl3S 0.0943(11) 0.0620(8) 0.1249(14) -0.0043(9) 0.0684(11) -0.0191(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C18 1.232(5) . ? O2 C22 1.379(5) . ? O2 C25 1.434(5) . ? O3 C32 1.387(5) . ? O3 C31 1.428(6) . ? O4 C38 1.224(4) . ? N1 C1 1.343(4) . ? N1 C5 1.351(4) . ? N1 H1A 0.8800 . ? N2 C18 1.379(5) . ? N2 C13 1.404(5) . ? N2 H2A 0.8800 . ? N3 C18 1.352(5) . ? N3 C19 1.426(5) . ? N3 H3A 0.8800 . ? N4 C38 1.364(5) . ? N4 C35 1.407(5) . ? N4 H4A 0.8800 . ? N5 C38 1.379(5) . ? N5 C39 1.402(5) . ? N5 H5A 0.8800 . ? C1 C2 1.388(5) . ? C1 C50 1.423(5) . ? C2 C3 1.388(5) . ? C2 H2B 0.9500 . ? C3 C4 1.373(5) . ? C3 H3B 0.9500 . ? C4 C5 1.395(5) . ? C4 H4B 0.9500 . ? C5 C6 1.414(5) . ? C6 C7 1.199(5) . ? C7 C8 1.429(5) . ? C8 C9 1.400(5) . ? C8 C13 1.408(5) . ? C9 C10 1.397(5) . ? C9 H9A 0.9500 . ? C10 C11 1.399(6) . ? C10 C14 1.535(5) . ? C11 C12 1.380(5) . ? C11 H11A 0.9500 . ? C12 C13 1.392(5) . ? C12 H12A 0.9500 . ? C14 C15 1.523(6) . ? C14 C17 1.530(6) . ? C14 C16 1.534(6) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C19 C20 1.375(6) . ? C19 C24 1.389(5) . ? C20 C21 1.396(6) . ? C20 H20A 0.9500 . ? C21 C22 1.379(6) . ? C21 H21A 0.9500 . ? C22 C23 1.369(6) . ? C23 C24 1.377(6) . ? C23 H23A 0.9500 . ? C24 H24A 0.9500 . ? C25 C26 1.514(6) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 C27 1.531(6) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C28 1.525(6) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 C29 1.507(6) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 C30 1.537(6) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 C31 1.500(7) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 C33 1.382(6) . ? C32 C37 1.390(6) . ? C33 C34 1.391(5) . ? C33 H33A 0.9500 . ? C34 C35 1.397(5) . ? C34 H34A 0.9500 . ? C35 C36 1.392(6) . ? C36 C37 1.390(6) . ? C36 H36A 0.9500 . ? C37 H37A 0.9500 . ? C39 C44 1.395(5) . ? C39 C40 1.411(5) . ? C40 C41 1.400(5) . ? C40 C49 1.424(5) . ? C41 C42 1.393(5) . ? C41 H41A 0.9500 . ? C42 C43 1.387(5) . ? C42 C45 1.533(5) . ? C43 C44 1.390(5) . ? C43 H43A 0.9500 . ? C44 H44A 0.9500 . ? C45 C47 1.522(6) . ? C45 C46 1.534(5) . ? C45 C48 1.536(7) . ? C46 H46A 0.9800 . ? C46 H46B 0.9800 . ? C46 H46C 0.9800 . ? C47 H47A 0.9800 . ? C47 H47B 0.9800 . ? C47 H47C 0.9800 . ? C48 H48A 0.9800 . ? C48 H48B 0.9800 . ? C48 H48C 0.9800 . ? C49 C50 1.191(5) . ? C1S Cl2S 1.725(5) . ? C1S Cl3S 1.735(5) . ? C1S Cl1S 1.781(7) . ? C1S H1SA 1.0000 . ? 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 C22 O2 C25 119.7(3) . . ? C32 O3 C31 112.0(3) . . ? C1 N1 C5 123.4(3) . . ? C1 N1 H1A 118.3 . . ? C5 N1 H1A 118.3 . . ? C18 N2 C13 126.9(3) . . ? C18 N2 H2A 116.5 . . ? C13 N2 H2A 116.5 . . ? C18 N3 C19 126.3(3) . . ? C18 N3 H3A 116.9 . . ? C19 N3 H3A 116.9 . . ? C38 N4 C35 125.7(3) . . ? C38 N4 H4A 117.1 . . ? C35 N4 H4A 117.1 . . ? C38 N5 C39 126.5(3) . . ? C38 N5 H5A 116.7 . . ? C39 N5 H5A 116.7 . . ? N1 C1 C2 119.1(3) . . ? N1 C1 C50 117.9(3) . . ? C2 C1 C50 122.9(3) . . ? C3 C2 C1 118.7(3) . . ? C3 C2 H2B 120.6 . . ? C1 C2 H2B 120.6 . . ? C4 C3 C2 121.2(3) . . ? C4 C3 H3B 119.4 . . ? C2 C3 H3B 119.4 . . ? C3 C4 C5 118.8(3) . . ? C3 C4 H4B 120.6 . . ? C5 C4 H4B 120.6 . . ? N1 C5 C4 118.9(3) . . ? N1 C5 C6 117.3(3) . . ? C4 C5 C6 123.8(3) . . ? C7 C6 C5 179.8(5) . . ? C6 C7 C8 178.7(4) . . ? C9 C8 C13 120.7(3) . . ? C9 C8 C7 118.9(3) . . ? C13 C8 C7 120.4(3) . . ? C10 C9 C8 121.4(3) . . ? C10 C9 H9A 119.3 . . ? C8 C9 H9A 119.3 . . ? C9 C10 C11 116.1(3) . . ? C9 C10 C14 122.1(3) . . ? C11 C10 C14 121.8(3) . . ? C12 C11 C10 123.8(3) . . ? C12 C11 H11A 118.1 . . ? C10 C11 H11A 118.1 . . ? C11 C12 C13 119.6(3) . . ? C11 C12 H12A 120.2 . . ? C13 C12 H12A 120.2 . . ? C12 C13 N2 123.3(3) . . ? C12 C13 C8 118.3(3) . . ? N2 C13 C8 118.4(3) . . ? C15 C14 C17 108.3(4) . . ? C15 C14 C10 112.4(3) . . ? C17 C14 C10 108.5(3) . . ? C15 C14 C16 108.7(4) . . ? C17 C14 C16 109.8(4) . . ? C10 C14 C16 109.1(3) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O1 C18 N3 124.3(3) . . ? O1 C18 N2 122.9(3) . . ? N3 C18 N2 112.8(3) . . ? C20 C19 C24 119.1(3) . . ? C20 C19 N3 123.8(3) . . ? C24 C19 N3 117.0(3) . . ? C19 C20 C21 120.3(4) . . ? C19 C20 H20A 119.9 . . ? C21 C20 H20A 119.9 . . ? C22 C21 C20 119.7(4) . . ? C22 C21 H21A 120.2 . . ? C20 C21 H21A 120.2 . . ? C23 C22 O2 114.9(4) . . ? C23 C22 C21 120.1(4) . . ? O2 C22 C21 124.9(4) . . ? C22 C23 C24 120.3(4) . . ? C22 C23 H23A 119.9 . . ? C24 C23 H23A 119.9 . . ? C23 C24 C19 120.5(4) . . ? C23 C24 H24A 119.8 . . ? C19 C24 H24A 119.8 . . ? O2 C25 C26 112.7(3) . . ? O2 C25 H25A 109.1 . . ? C26 C25 H25A 109.1 . . ? O2 C25 H25B 109.1 . . ? C26 C25 H25B 109.1 . . ? H25A C25 H25B 107.8 . . ? C25 C26 C27 113.9(4) . . ? C25 C26 H26A 108.8 . . ? C27 C26 H26A 108.8 . . ? C25 C26 H26B 108.8 . . ? C27 C26 H26B 108.8 . . ? H26A C26 H26B 107.7 . . ? C28 C27 C26 115.9(4) . . ? C28 C27 H27A 108.3 . . ? C26 C27 H27A 108.3 . . ? C28 C27 H27B 108.3 . . ? C26 C27 H27B 108.3 . . ? H27A C27 H27B 107.4 . . ? C29 C28 C27 113.8(4) . . ? C29 C28 H28A 108.8 . . ? C27 C28 H28A 108.8 . . ? C29 C28 H28B 108.8 . . ? C27 C28 H28B 108.8 . . ? H28A C28 H28B 107.7 . . ? C28 C29 C30 110.7(4) . . ? C28 C29 H29A 109.5 . . ? C30 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? C30 C29 H29B 109.5 . . ? H29A C29 H29B 108.1 . . ? C31 C30 C29 111.2(4) . . ? C31 C30 H30A 109.4 . . ? C29 C30 H30A 109.4 . . ? C31 C30 H30B 109.4 . . ? C29 C30 H30B 109.4 . . ? H30A C30 H30B 108.0 . . ? O3 C31 C30 113.5(4) . . ? O3 C31 H31A 108.9 . . ? C30 C31 H31A 108.9 . . ? O3 C31 H31B 108.9 . . ? C30 C31 H31B 108.9 . . ? H31A C31 H31B 107.7 . . ? C33 C32 O3 120.1(4) . . ? C33 C32 C37 119.2(4) . . ? O3 C32 C37 120.7(4) . . ? C32 C33 C34 120.3(4) . . ? C32 C33 H33A 119.8 . . ? C34 C33 H33A 119.8 . . ? C33 C34 C35 120.4(4) . . ? C33 C34 H34A 119.8 . . ? C35 C34 H34A 119.8 . . ? C36 C35 C34 119.4(4) . . ? C36 C35 N4 122.7(3) . . ? C34 C35 N4 117.8(3) . . ? C37 C36 C35 119.5(4) . . ? C37 C36 H36A 120.2 . . ? C35 C36 H36A 120.2 . . ? C32 C37 C36 121.1(4) . . ? C32 C37 H37A 119.4 . . ? C36 C37 H37A 119.4 . . ? O4 C38 N4 123.7(3) . . ? O4 C38 N5 123.9(3) . . ? N4 C38 N5 112.4(3) . . ? N5 C39 C44 124.4(3) . . ? N5 C39 C40 117.9(3) . . ? C44 C39 C40 117.7(3) . . ? C41 C40 C39 120.5(3) . . ? C41 C40 C49 117.9(3) . . ? C39 C40 C49 121.7(3) . . ? C42 C41 C40 121.7(3) . . ? C42 C41 H41A 119.2 . . ? C40 C41 H41A 119.2 . . ? C43 C42 C41 116.9(3) . . ? C43 C42 C45 123.9(3) . . ? C41 C42 C45 119.1(3) . . ? C44 C43 C42 122.7(3) . . ? C44 C43 H43A 118.7 . . ? C42 C43 H43A 118.7 . . ? C43 C44 C39 120.5(3) . . ? C43 C44 H44A 119.7 . . ? C39 C44 H44A 119.7 . . ? C47 C45 C46 109.3(4) . . ? C47 C45 C42 109.7(3) . . ? C46 C45 C42 111.9(3) . . ? C47 C45 C48 108.4(4) . . ? C46 C45 C48 108.9(4) . . ? C42 C45 C48 108.5(3) . . ? C45 C46 H46A 109.5 . . ? C45 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? C45 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? C45 C47 H47A 109.5 . . ? C45 C47 H47B 109.5 . . ? H47A C47 H47B 109.5 . . ? C45 C47 H47C 109.5 . . ? H47A C47 H47C 109.5 . . ? H47B C47 H47C 109.5 . . ? C45 C48 H48A 109.5 . . ? C45 C48 H48B 109.5 . . ? H48A C48 H48B 109.5 . . ? C45 C48 H48C 109.5 . . ? H48A C48 H48C 109.5 . . ? H48B C48 H48C 109.5 . . ? C50 C49 C40 175.7(4) . . ? C49 C50 C1 173.7(4) . . ? Cl2S C1S Cl3S 110.5(3) . . ? Cl2S C1S Cl1S 110.1(3) . . ? Cl3S C1S Cl1S 110.4(3) . . ? Cl2S C1S H1SA 108.6 . . ? Cl3S C1S H1SA 108.6 . . ? Cl1S C1S H1SA 108.6 . . ? 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 C5 N1 C1 C2 0.6(5) . . . . ? C5 N1 C1 C50 -176.1(3) . . . . ? N1 C1 C2 C3 0.2(6) . . . . ? C50 C1 C2 C3 176.8(4) . . . . ? C1 C2 C3 C4 -0.3(6) . . . . ? C2 C3 C4 C5 -0.4(6) . . . . ? C1 N1 C5 C4 -1.3(5) . . . . ? C1 N1 C5 C6 178.5(3) . . . . ? C3 C4 C5 N1 1.2(5) . . . . ? C3 C4 C5 C6 -178.7(4) . . . . ? N1 C5 C6 C7 -65(100) . . . . ? C4 C5 C6 C7 115(100) . . . . ? C5 C6 C7 C8 101(100) . . . . ? C6 C7 C8 C9 166(18) . . . . ? C6 C7 C8 C13 -15(18) . . . . ? C13 C8 C9 C10 -0.2(6) . . . . ? C7 C8 C9 C10 179.5(3) . . . . ? C8 C9 C10 C11 0.2(6) . . . . ? C8 C9 C10 C14 -177.8(4) . . . . ? C9 C10 C11 C12 0.0(6) . . . . ? C14 C10 C11 C12 178.0(4) . . . . ? C10 C11 C12 C13 -0.2(6) . . . . ? C11 C12 C13 N2 -178.7(4) . . . . ? C11 C12 C13 C8 0.3(5) . . . . ? C18 N2 C13 C12 -31.5(6) . . . . ? C18 N2 C13 C8 149.5(4) . . . . ? C9 C8 C13 C12 -0.1(5) . . . . ? C7 C8 C13 C12 -179.8(3) . . . . ? C9 C8 C13 N2 178.9(3) . . . . ? C7 C8 C13 N2 -0.8(5) . . . . ? C9 C10 C14 C15 -0.8(6) . . . . ? C11 C10 C14 C15 -178.7(4) . . . . ? C9 C10 C14 C17 118.9(4) . . . . ? C11 C10 C14 C17 -58.9(5) . . . . ? C9 C10 C14 C16 -121.4(4) . . . . ? C11 C10 C14 C16 60.7(5) . . . . ? C19 N3 C18 O1 9.3(6) . . . . ? C19 N3 C18 N2 -170.7(3) . . . . ? C13 N2 C18 O1 0.2(6) . . . . ? C13 N2 C18 N3 -179.8(3) . . . . ? C18 N3 C19 C20 -46.4(6) . . . . ? C18 N3 C19 C24 135.1(4) . . . . ? C24 C19 C20 C21 1.0(6) . . . . ? N3 C19 C20 C21 -177.5(4) . . . . ? C19 C20 C21 C22 0.4(6) . . . . ? C25 O2 C22 C23 -165.0(4) . . . . ? C25 O2 C22 C21 18.7(6) . . . . ? C20 C21 C22 C23 -1.3(6) . . . . ? C20 C21 C22 O2 174.8(4) . . . . ? O2 C22 C23 C24 -175.6(4) . . . . ? C21 C22 C23 C24 0.9(6) . . . . ? C22 C23 C24 C19 0.5(6) . . . . ? C20 C19 C24 C23 -1.4(6) . . . . ? N3 C19 C24 C23 177.1(3) . . . . ? C22 O2 C25 C26 79.9(5) . . . . ? O2 C25 C26 C27 75.1(4) . . . . ? C25 C26 C27 C28 -65.3(5) . . . . ? C26 C27 C28 C29 -68.1(5) . . . . ? C27 C28 C29 C30 175.7(4) . . . . ? C28 C29 C30 C31 -177.2(4) . . . . ? C32 O3 C31 C30 -77.2(5) . . . . ? C29 C30 C31 O3 174.4(4) . . . . ? C31 O3 C32 C33 -84.6(5) . . . . ? C31 O3 C32 C37 97.9(5) . . . . ? O3 C32 C33 C34 180.0(4) . . . . ? C37 C32 C33 C34 -2.4(6) . . . . ? C32 C33 C34 C35 -0.2(6) . . . . ? C33 C34 C35 C36 1.9(6) . . . . ? C33 C34 C35 N4 -175.8(3) . . . . ? C38 N4 C35 C36 26.0(6) . . . . ? C38 N4 C35 C34 -156.4(4) . . . . ? C34 C35 C36 C37 -1.0(6) . . . . ? N4 C35 C36 C37 176.6(4) . . . . ? C33 C32 C37 C36 3.3(7) . . . . ? O3 C32 C37 C36 -179.1(4) . . . . ? C35 C36 C37 C32 -1.6(7) . . . . ? C35 N4 C38 O4 3.6(6) . . . . ? C35 N4 C38 N5 -176.4(3) . . . . ? C39 N5 C38 O4 -2.0(6) . . . . ? C39 N5 C38 N4 178.0(3) . . . . ? C38 N5 C39 C44 2.8(6) . . . . ? C38 N5 C39 C40 -175.4(3) . . . . ? N5 C39 C40 C41 176.3(3) . . . . ? C44 C39 C40 C41 -2.0(5) . . . . ? N5 C39 C40 C49 -3.9(5) . . . . ? C44 C39 C40 C49 177.8(3) . . . . ? C39 C40 C41 C42 0.3(5) . . . . ? C49 C40 C41 C42 -179.5(3) . . . . ? C40 C41 C42 C43 1.4(5) . . . . ? C40 C41 C42 C45 -176.7(3) . . . . ? C41 C42 C43 C44 -1.4(6) . . . . ? C45 C42 C43 C44 176.7(4) . . . . ? C42 C43 C44 C39 -0.4(6) . . . . ? N5 C39 C44 C43 -176.1(3) . . . . ? C40 C39 C44 C43 2.0(5) . . . . ? C43 C42 C45 C47 125.8(5) . . . . ? C41 C42 C45 C47 -56.2(5) . . . . ? C43 C42 C45 C46 4.3(6) . . . . ? C41 C42 C45 C46 -177.7(4) . . . . ? C43 C42 C45 C48 -115.9(4) . . . . ? C41 C42 C45 C48 62.1(5) . . . . ? C41 C40 C49 C50 39(5) . . . . ? C39 C40 C49 C50 -141(5) . . . . ? C40 C49 C50 C1 18(8) . . . . ? N1 C1 C50 C49 131(3) . . . . ? C2 C1 C50 C49 -46(4) . . . . ? 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 H1A Cl1 0.88 2.15 3.025(3) 174.5 . N2 H2A Cl1 0.88 2.69 3.500(3) 153.0 . N3 H3A Cl1 0.88 2.34 3.194(3) 162.9 . N4 H4A Cl1 0.88 2.33 3.194(3) 168.3 . N5 H5A Cl1 0.88 2.74 3.536(3) 151.7 . _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 67.83 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 1.824 _refine_diff_density_min -1.053 _refine_diff_density_rms 0.101 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.250 -0.007 0.250 385.9 96.2 2 0.750 -0.042 0.750 385.9 96.6 _platon_squeeze_details ; ? ; _database_code_depnum_ccdc_archive 'CCDC 968267' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_mh90a _audit_creation_method SHELXLTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C50H53N5O4) (H2O) 0.5(C6H14)' _chemical_formula_sum 'C53 H62 N5 O5' _chemical_formula_weight 849.08 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 Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 24.0752(18) _cell_length_b 9.9609(7) _cell_length_c 45.509(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 10913.6(14) _cell_formula_units_Z 8 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 3990 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 18.64 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.034 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3640 _exptl_absorpt_coefficient_mu 0.067 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9875 _exptl_absorpt_correction_T_max 0.9954 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(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 'Bruker Apex CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 59833 _diffrn_reflns_av_R_equivalents 0.0709 _diffrn_reflns_av_sigmaI/netI 0.0561 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -54 _diffrn_reflns_limit_l_max 54 _diffrn_reflns_theta_min 0.89 _diffrn_reflns_theta_max 25.00 _reflns_number_total 9605 _reflns_number_gt 5951 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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. In the crystal structure a hexane solvent molecule, C6H14, disordered around an inversion center was treated by SQUEEZE [Van der Sluis,P. & Spek, A.L. (1990) Acta Cryst., Sect.A,A46,194-201.]. Corrections of the X-ray data by SQUEEZE (223 electron/cell) was close to the required values (200 electron/cell) for four molecules in the full unit cell. ; _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^)+(0.1148P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9605 _refine_ls_number_parameters 699 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1058 _refine_ls_R_factor_gt 0.0636 _refine_ls_wR_factor_ref 0.2000 _refine_ls_wR_factor_gt 0.1759 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.014 _refine_ls_shift/su_max 0.002 _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 O1 O 0.35804(8) -0.20870(18) 0.10020(4) 0.0460(5) Uani 1 1 d . . . O2 O 0.17400(9) -0.4703(2) 0.02181(5) 0.0557(6) Uani 1 1 d . . . O3 O 0.02568(8) -0.21505(19) -0.00413(4) 0.0485(5) Uani 1 1 d . . . O4 O -0.00711(10) -0.0066(2) 0.12659(5) 0.0723(8) Uani 1 1 d . . . O5 O 0.22806(11) 0.1209(2) 0.12694(5) 0.0512(6) Uani 1 1 d . . . N1 N 0.24590(9) 0.3417(2) 0.16941(5) 0.0377(5) Uani 1 1 d . . . N2 N 0.35318(10) 0.0108(2) 0.11477(5) 0.0379(6) Uani 1 1 d . . . N3 N 0.27940(10) -0.0871(2) 0.09156(5) 0.0386(6) Uani 1 1 d . . . N4 N 0.06838(10) 0.0578(2) 0.10036(5) 0.0409(6) Uani 1 1 d . . . N5 N 0.05199(11) 0.1492(2) 0.14565(5) 0.0424(6) Uani 1 1 d . . . C1 C 0.20671(11) 0.4127(3) 0.18382(6) 0.0380(7) Uani 1 1 d . . . C2 C 0.21900(13) 0.5257(3) 0.20061(6) 0.0427(7) Uani 1 1 d . . . C3 C 0.27346(13) 0.5676(3) 0.20271(7) 0.0434(7) Uani 1 1 d . . . C4 C 0.31357(14) 0.4973(3) 0.18830(6) 0.0408(7) Uani 1 1 d . . . C5 C 0.29861(11) 0.3845(3) 0.17190(6) 0.0356(6) Uani 1 1 d . . . C6 C 0.34073(12) 0.3037(3) 0.15825(6) 0.0400(7) Uani 1 1 d . . . C7 C 0.37748(12) 0.2335(3) 0.14939(6) 0.0390(7) Uani 1 1 d . . . C8 C 0.42105(11) 0.1472(3) 0.13950(5) 0.0350(6) Uani 1 1 d . . . C9 C 0.47598(12) 0.1758(3) 0.14711(6) 0.0420(7) Uani 1 1 d . . . C10 C 0.51959(12) 0.0935(3) 0.13896(6) 0.0448(7) Uani 1 1 d . . . C11 C 0.50621(13) -0.0179(3) 0.12190(6) 0.0458(7) Uani 1 1 d . . . C12 C 0.45267(12) -0.0464(3) 0.11354(7) 0.0429(7) Uani 1 1 d . . . C13 C 0.40848(11) 0.0342(3) 0.12247(5) 0.0350(6) Uani 1 1 d . . . C14 C 0.58025(12) 0.1258(3) 0.14682(7) 0.0546(8) Uani 1 1 d . . . C15 C 0.58423(18) 0.2327(6) 0.16993(13) 0.144(3) Uani 1 1 d . . . H15A H 0.6234 0.2507 0.1743 0.216 Uiso 1 1 calc R . . H15B H 0.5654 0.2022 0.1878 0.216 Uiso 1 1 calc R . . H15C H 0.5665 0.3150 0.1628 0.216 Uiso 1 1 calc R . . C16 C 0.60812(18) 0.1866(6) 0.11998(11) 0.1226(19) Uani 1 1 d . . . H16A H 0.6469 0.2080 0.1246 0.184 Uiso 1 1 calc R . . H16B H 0.5885 0.2688 0.1143 0.184 Uiso 1 1 calc R . . H16C H 0.6069 0.1222 0.1037 0.184 Uiso 1 1 calc R . . C17 C 0.6103(2) 0.0015(5) 0.15587(14) 0.130(2) Uani 1 1 d . . . H17A H 0.6489 0.0240 0.1608 0.195 Uiso 1 1 calc R . . H17B H 0.6099 -0.0634 0.1397 0.195 Uiso 1 1 calc R . . H17C H 0.5921 -0.0377 0.1731 0.195 Uiso 1 1 calc R . . C18 C 0.33150(11) -0.1013(3) 0.10190(5) 0.0363(6) Uani 1 1 d . . . C19 C 0.25148(11) -0.1821(3) 0.07363(5) 0.0355(6) Uani 1 1 d . . . C20 C 0.19411(12) -0.1949(3) 0.07504(6) 0.0405(7) Uani 1 1 d . . . C21 C 0.16635(13) -0.2870(3) 0.05740(6) 0.0433(7) Uani 1 1 d . . . C22 C 0.19632(12) -0.3695(3) 0.03886(6) 0.0407(7) Uani 1 1 d . . . C23 C 0.25312(13) -0.3560(3) 0.03701(7) 0.0459(7) Uani 1 1 d . . . C24 C 0.28066(13) -0.2621(3) 0.05381(6) 0.0409(7) Uani 1 1 d . . . C25 C 0.11591(14) -0.4948(4) 0.02288(8) 0.0525(8) Uani 1 1 d . . . C26 C 0.10423(17) -0.6082(3) 0.00166(8) 0.0571(9) Uani 1 1 d . . . C27 C 0.12563(16) -0.5859(3) -0.02923(8) 0.0579(9) Uani 1 1 d . . . C28 C 0.11136(14) -0.4498(3) -0.04248(8) 0.0532(8) Uani 1 1 d . . . C29 C 0.04938(15) -0.4241(3) -0.04546(7) 0.0501(8) Uani 1 1 d . . . C30 C 0.03411(18) -0.2803(3) -0.05409(7) 0.0544(9) Uani 1 1 d . . . C31 C 0.05121(15) -0.1758(3) -0.03117(6) 0.0472(8) Uani 1 1 d . . . C32 C 0.03806(11) -0.1435(3) 0.02063(6) 0.0375(7) Uani 1 1 d . . . C33 C 0.07056(13) -0.0298(3) 0.02140(7) 0.0434(7) Uani 1 1 d . . . C34 C 0.07967(12) 0.0348(3) 0.04809(6) 0.0405(7) Uani 1 1 d . . . C35 C 0.05720(11) -0.0137(3) 0.07398(6) 0.0358(6) Uani 1 1 d . . . C36 C 0.02533(12) -0.1306(3) 0.07310(7) 0.0419(7) Uani 1 1 d . . . C37 C 0.01563(12) -0.1934(3) 0.04652(6) 0.0435(7) Uani 1 1 d . . . C38 C 0.03412(12) 0.0616(3) 0.12423(6) 0.0424(7) Uani 1 1 d . . . C39 C 0.02244(11) 0.1881(3) 0.17075(6) 0.0379(7) Uani 1 1 d . . . C40 C -0.03096(13) 0.1445(3) 0.17735(7) 0.0503(8) Uani 1 1 d . . . C41 C -0.05752(14) 0.1875(3) 0.20256(7) 0.0548(9) Uani 1 1 d . . . C42 C -0.03316(12) 0.2742(3) 0.22278(6) 0.0482(8) Uani 1 1 d . A . C43 C 0.02016(13) 0.3173(3) 0.21609(6) 0.0438(7) Uani 1 1 d . . . C44 C 0.04825(11) 0.2763(3) 0.19061(6) 0.0383(6) Uani 1 1 d . . . C45 C -0.06403(14) 0.3170(4) 0.25050(7) 0.0610(9) Uani 1 1 d D . . C46 C -0.0315(2) 0.4069(6) 0.27014(12) 0.0866(17) Uani 0.772(4) 1 d PD A 1 H46A H -0.0066 0.3529 0.2824 0.130 Uiso 0.772(4) 1 calc PR A 1 H46B H -0.0569 0.4579 0.2827 0.130 Uiso 0.772(4) 1 calc PR A 1 H46C H -0.0094 0.4692 0.2582 0.130 Uiso 0.772(4) 1 calc PR A 1 C47 C -0.1194(3) 0.3720(10) 0.24230(12) 0.142(4) Uani 0.772(4) 1 d PD A 1 H47A H -0.1464 0.2986 0.2410 0.212 Uiso 0.772(4) 1 calc PR A 1 H47B H -0.1167 0.4172 0.2232 0.212 Uiso 0.772(4) 1 calc PR A 1 H47C H -0.1315 0.4365 0.2573 0.212 Uiso 0.772(4) 1 calc PR A 1 C48 C -0.0749(3) 0.1905(6) 0.26947(12) 0.0945(19) Uani 0.772(4) 1 d PD A 1 H48A H -0.0520 0.1161 0.2623 0.142 Uiso 0.772(4) 1 calc PR A 1 H48B H -0.1143 0.1659 0.2682 0.142 Uiso 0.772(4) 1 calc PR A 1 H48C H -0.0653 0.2095 0.2900 0.142 Uiso 0.772(4) 1 calc PR A 1 C46A C -0.0249(9) 0.287(4) 0.2749(4) 0.142(4) Uani 0.228(4) 1 d PD A 2 H46D H -0.0187 0.1897 0.2759 0.212 Uiso 0.228(4) 1 calc PR A 2 H46E H -0.0408 0.3182 0.2935 0.212 Uiso 0.228(4) 1 calc PR A 2 H46F H 0.0105 0.3326 0.2713 0.212 Uiso 0.228(4) 1 calc PR A 2 C47A C -0.0695(9) 0.4834(14) 0.2478(4) 0.0945(19) Uani 0.228(4) 1 d PD A 2 H47D H -0.0490 0.5145 0.2305 0.142 Uiso 0.228(4) 1 calc PR A 2 H47E H -0.0540 0.5254 0.2655 0.142 Uiso 0.228(4) 1 calc PR A 2 H47F H -0.1087 0.5082 0.2459 0.142 Uiso 0.228(4) 1 calc PR A 2 C48A C -0.1169(8) 0.259(2) 0.2560(5) 0.0866(17) Uani 0.228(4) 1 d PD A 2 H48D H -0.1124 0.1625 0.2599 0.130 Uiso 0.228(4) 1 calc PR A 2 H48E H -0.1407 0.2710 0.2387 0.130 Uiso 0.228(4) 1 calc PR A 2 H48F H -0.1339 0.3021 0.2730 0.130 Uiso 0.228(4) 1 calc PR A 2 C49 C 0.10395(12) 0.3233(3) 0.18586(6) 0.0396(7) Uani 1 1 d . . . C50 C 0.15051(12) 0.3622(3) 0.18324(6) 0.0384(7) Uani 1 1 d . . . H1OA H 0.2346(16) 0.195(4) 0.1436(9) 0.095(13) Uiso 1 1 d . . . H1OB H 0.2079(19) 0.159(4) 0.1180(10) 0.096(18) Uiso 1 1 d . . . H2 H 0.1899(12) 0.569(3) 0.2108(6) 0.049(8) Uiso 1 1 d . . . H2N H 0.3304(13) 0.078(3) 0.1179(6) 0.051(9) Uiso 1 1 d . . . H3 H 0.2847(11) 0.639(3) 0.2147(6) 0.040(8) Uiso 1 1 d . . . H3N H 0.2605(12) -0.013(3) 0.0986(6) 0.046(8) Uiso 1 1 d . . . H4 H 0.3480(12) 0.523(3) 0.1891(6) 0.035(8) Uiso 1 1 d . . . H4N H 0.0942(11) 0.122(3) 0.0991(6) 0.036(8) Uiso 1 1 d . . . H5N H 0.0815(13) 0.203(3) 0.1431(6) 0.053(9) Uiso 1 1 d . . . H9 H 0.4871(14) 0.254(3) 0.1589(7) 0.069(10) Uiso 1 1 d . . . H11 H 0.5399(12) -0.080(3) 0.1161(6) 0.044(7) Uiso 1 1 d . . . H12 H 0.4446(12) -0.124(3) 0.1016(7) 0.058(9) Uiso 1 1 d . . . H20 H 0.1733(12) -0.137(3) 0.0892(6) 0.049(8) Uiso 1 1 d . . . H21 H 0.1266(13) -0.297(3) 0.0580(6) 0.045(8) Uiso 1 1 d . . . H23 H 0.2706(13) -0.411(3) 0.0247(7) 0.063(10) Uiso 1 1 d . . . H24 H 0.3198(13) -0.253(3) 0.0528(6) 0.043(8) Uiso 1 1 d . . . H25A H 0.0972(12) -0.412(3) 0.0171(6) 0.054(9) Uiso 1 1 d . . . H25B H 0.1051(12) -0.521(3) 0.0434(7) 0.053(9) Uiso 1 1 d . . . H26A H 0.1209(15) -0.693(3) 0.0095(8) 0.080(11) Uiso 1 1 d . . . H26B H 0.0629(14) -0.625(3) 0.0032(7) 0.061(9) Uiso 1 1 d . . . H27A H 0.1667(13) -0.597(3) -0.0294(6) 0.049(8) Uiso 1 1 d . . . H27B H 0.1107(13) -0.655(3) -0.0422(7) 0.058(9) Uiso 1 1 d . . . H28A H 0.1290(14) -0.446(3) -0.0628(8) 0.073(10) Uiso 1 1 d . . . H28B H 0.1336(12) -0.375(3) -0.0289(7) 0.059(9) Uiso 1 1 d . . . H29A H 0.0337(11) -0.485(3) -0.0605(6) 0.044(8) Uiso 1 1 d . . . H29B H 0.0279(13) -0.446(3) -0.0280(8) 0.060(10) Uiso 1 1 d . . . H30A H 0.0546(14) -0.252(3) -0.0720(8) 0.071(11) Uiso 1 1 d . . . H30B H -0.0076(13) -0.266(3) -0.0579(6) 0.052(9) Uiso 1 1 d . . . H31A H 0.0378(11) -0.074(3) -0.0378(6) 0.041(7) Uiso 1 1 d . . . H31B H 0.0905(12) -0.172(2) -0.0259(6) 0.037(7) Uiso 1 1 d . . . H33 H 0.0861(13) 0.007(3) 0.0030(7) 0.067(10) Uiso 1 1 d . . . H34 H 0.1011(10) 0.127(2) 0.0479(5) 0.029(6) Uiso 1 1 d . . . H36 H 0.0106(13) -0.172(3) 0.0916(7) 0.062(9) Uiso 1 1 d . . . H37 H -0.0033(13) -0.279(3) 0.0470(7) 0.062(9) Uiso 1 1 d . . . H40 H -0.0508(14) 0.096(3) 0.1638(8) 0.071(11) Uiso 1 1 d . . . H41 H -0.0930(14) 0.152(3) 0.2069(7) 0.064(10) Uiso 1 1 d . . . H43 H 0.0390(10) 0.384(3) 0.2289(6) 0.038(7) 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 0.0406(12) 0.0386(11) 0.0589(13) -0.0034(9) -0.0052(9) 0.0076(9) O2 0.0480(14) 0.0558(13) 0.0634(14) -0.0147(11) -0.0166(11) -0.0027(10) O3 0.0598(14) 0.0472(12) 0.0386(11) -0.0130(9) -0.0045(10) -0.0066(10) O4 0.0705(17) 0.0762(16) 0.0702(16) -0.0349(13) 0.0323(13) -0.0374(13) O5 0.0673(16) 0.0425(13) 0.0439(13) 0.0045(11) 0.0054(12) 0.0106(12) N1 0.0393(14) 0.0370(13) 0.0369(12) 0.0027(10) -0.0007(11) 0.0033(11) N2 0.0341(14) 0.0361(13) 0.0434(14) -0.0044(11) -0.0025(11) 0.0029(11) N3 0.0365(14) 0.0353(13) 0.0441(14) -0.0040(11) -0.0053(11) 0.0038(11) N4 0.0454(15) 0.0421(14) 0.0352(13) -0.0107(11) 0.0050(11) -0.0131(12) N5 0.0396(15) 0.0473(15) 0.0404(14) -0.0131(11) 0.0073(11) -0.0060(12) C1 0.0407(17) 0.0384(16) 0.0348(15) 0.0048(12) -0.0011(13) 0.0046(13) C2 0.049(2) 0.0370(16) 0.0422(17) -0.0038(13) -0.0028(15) 0.0082(14) C3 0.053(2) 0.0353(16) 0.0423(17) -0.0016(14) -0.0097(15) 0.0015(14) C4 0.0404(19) 0.0375(16) 0.0446(17) 0.0033(13) -0.0053(14) -0.0021(14) C5 0.0373(16) 0.0364(15) 0.0331(15) 0.0057(12) -0.0021(12) 0.0012(13) C6 0.0392(17) 0.0389(16) 0.0418(16) 0.0024(13) -0.0032(14) -0.0061(14) C7 0.0388(17) 0.0408(16) 0.0373(15) 0.0013(13) -0.0032(13) -0.0046(14) C8 0.0352(16) 0.0368(15) 0.0329(14) 0.0023(12) 0.0016(12) -0.0006(12) C9 0.0402(18) 0.0458(17) 0.0400(16) -0.0010(14) -0.0012(13) -0.0016(14) C10 0.0392(18) 0.0551(19) 0.0402(16) 0.0008(14) 0.0008(13) 0.0002(14) C11 0.0394(18) 0.0564(19) 0.0418(17) -0.0038(15) 0.0047(14) 0.0030(15) C12 0.0395(18) 0.0475(18) 0.0417(16) -0.0059(14) 0.0038(14) 0.0006(14) C13 0.0348(16) 0.0408(15) 0.0294(14) 0.0049(12) 0.0021(12) -0.0014(12) C14 0.0333(17) 0.070(2) 0.061(2) -0.0102(17) -0.0058(15) -0.0004(16) C15 0.052(3) 0.187(6) 0.193(6) -0.110(5) -0.042(3) 0.006(3) C16 0.055(3) 0.177(5) 0.136(4) 0.030(4) 0.000(3) -0.047(3) C17 0.070(3) 0.105(4) 0.216(6) 0.039(4) -0.076(4) -0.006(3) C18 0.0375(17) 0.0377(16) 0.0336(14) 0.0023(12) 0.0006(12) 0.0000(13) C19 0.0400(17) 0.0342(14) 0.0322(14) 0.0057(12) -0.0036(12) -0.0002(12) C20 0.0376(17) 0.0464(17) 0.0375(16) 0.0027(13) -0.0009(13) 0.0082(14) C21 0.0333(17) 0.0503(18) 0.0462(17) 0.0025(14) -0.0090(14) 0.0003(14) C22 0.0440(18) 0.0387(15) 0.0394(16) 0.0026(13) -0.0100(14) -0.0005(13) C23 0.047(2) 0.0426(17) 0.0476(18) -0.0062(15) -0.0005(15) 0.0047(15) C24 0.0349(17) 0.0467(17) 0.0410(16) -0.0054(13) 0.0030(13) -0.0016(14) C25 0.049(2) 0.056(2) 0.053(2) 0.0042(17) -0.0153(16) -0.0091(16) C26 0.061(2) 0.047(2) 0.064(2) 0.0051(16) -0.0186(19) -0.0087(17) C27 0.058(2) 0.052(2) 0.064(2) -0.0140(18) -0.0107(19) 0.0046(17) C28 0.057(2) 0.0533(19) 0.049(2) -0.0058(16) 0.0011(17) 0.0045(16) C29 0.062(2) 0.0485(19) 0.0394(18) -0.0107(15) -0.0099(17) -0.0030(16) C30 0.077(3) 0.0468(19) 0.0389(18) -0.0080(15) -0.0132(18) 0.0050(17) C31 0.060(2) 0.0454(19) 0.0361(16) -0.0051(14) -0.0046(15) 0.0000(16) C32 0.0404(16) 0.0333(15) 0.0387(16) -0.0072(12) -0.0070(13) 0.0010(12) C33 0.0509(19) 0.0420(17) 0.0374(17) -0.0035(13) -0.0002(14) -0.0033(14) C34 0.0447(18) 0.0374(16) 0.0396(16) -0.0044(13) 0.0014(13) -0.0039(13) C35 0.0356(16) 0.0356(15) 0.0364(15) -0.0053(12) -0.0048(12) -0.0004(12) C36 0.0453(18) 0.0428(17) 0.0377(17) -0.0019(13) 0.0008(14) -0.0051(14) C37 0.0426(17) 0.0408(17) 0.0471(18) -0.0063(14) -0.0030(14) -0.0087(14) C38 0.0441(18) 0.0438(17) 0.0394(16) -0.0067(13) 0.0043(14) -0.0054(14) C39 0.0385(17) 0.0392(15) 0.0359(15) -0.0045(12) 0.0046(13) 0.0035(12) C40 0.0420(19) 0.060(2) 0.0482(19) -0.0121(16) 0.0034(15) -0.0078(16) C41 0.0427(19) 0.067(2) 0.055(2) -0.0136(17) 0.0140(16) -0.0079(17) C42 0.0456(19) 0.0578(19) 0.0411(17) -0.0043(14) 0.0075(14) 0.0032(15) C43 0.0475(19) 0.0473(17) 0.0368(16) -0.0084(14) -0.0004(14) 0.0025(14) C44 0.0395(16) 0.0393(15) 0.0362(15) -0.0032(12) 0.0029(13) 0.0015(12) C45 0.053(2) 0.080(2) 0.0495(19) -0.0164(18) 0.0154(16) -0.0014(18) C46 0.092(4) 0.104(4) 0.064(3) -0.042(3) 0.030(3) -0.004(3) C47 0.101(5) 0.264(10) 0.060(3) -0.041(5) 0.011(3) 0.099(6) C48 0.104(5) 0.115(4) 0.065(3) -0.021(3) 0.041(3) -0.032(4) C46A 0.101(5) 0.264(10) 0.060(3) -0.041(5) 0.011(3) 0.099(6) C47A 0.104(5) 0.115(4) 0.065(3) -0.021(3) 0.041(3) -0.032(4) C48A 0.092(4) 0.104(4) 0.064(3) -0.042(3) 0.030(3) -0.004(3) C49 0.0426(18) 0.0402(16) 0.0361(15) -0.0072(13) 0.0006(13) 0.0042(14) C50 0.0405(18) 0.0407(16) 0.0339(15) -0.0018(12) 0.0023(13) 0.0048(13) _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 C18 1.248(3) . ? O2 C22 1.377(3) . ? O2 C25 1.421(4) . ? O3 C32 1.367(3) . ? O3 C31 1.430(3) . ? O4 C38 1.207(3) . ? O5 H1OA 1.07(4) . ? O5 H1OB 0.74(4) . ? N1 C5 1.344(3) . ? N1 C1 1.349(3) . ? N2 C18 1.364(3) . ? N2 C13 1.396(3) . ? N2 H2N 0.88(3) . ? N3 C18 1.347(3) . ? N3 C19 1.419(3) . ? N3 H3N 0.92(3) . ? N4 C38 1.365(3) . ? N4 C35 1.421(3) . ? N4 H4N 0.89(3) . ? N5 C38 1.378(4) . ? N5 C39 1.401(3) . ? N5 H5N 0.90(3) . ? C1 C2 1.392(4) . ? C1 C50 1.444(4) . ? C2 C3 1.379(4) . ? C2 H2 0.95(3) . ? C3 C4 1.361(4) . ? C3 H3 0.94(3) . ? C4 C5 1.396(4) . ? C4 H4 0.87(3) . ? C5 C6 1.436(4) . ? C6 C7 1.198(4) . ? C7 C8 1.429(4) . ? C8 C9 1.397(4) . ? C8 C13 1.400(4) . ? C9 C10 1.383(4) . ? C9 H9 0.98(3) . ? C10 C11 1.392(4) . ? C10 C14 1.537(4) . ? C11 C12 1.374(4) . ? C11 H11 1.05(3) . ? C12 C13 1.393(4) . ? C12 H12 0.97(3) . ? C14 C17 1.493(5) . ? C14 C15 1.500(5) . ? C14 C16 1.519(5) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C19 C20 1.388(4) . ? C19 C24 1.394(4) . ? C20 C21 1.391(4) . ? C20 H20 1.00(3) . ? C21 C22 1.381(4) . ? C21 H21 0.96(3) . ? C22 C23 1.377(4) . ? C23 C24 1.378(4) . ? C23 H23 0.89(3) . ? C24 H24 0.95(3) . ? C25 C26 1.512(4) . ? C25 H25A 0.98(3) . ? C25 H25B 1.00(3) . ? C26 C27 1.514(5) . ? C26 H26A 1.00(4) . ? C26 H26B 1.01(3) . ? C27 C28 1.523(5) . ? C27 H27A 1.00(3) . ? C27 H27B 0.98(3) . ? C28 C29 1.520(5) . ? C28 H28A 1.02(4) . ? C28 H28B 1.10(3) . ? C29 C30 1.530(4) . ? C29 H29A 0.99(3) . ? C29 H29B 0.97(3) . ? C30 C31 1.530(4) . ? C30 H30A 0.99(4) . ? C30 H30B 1.03(3) . ? C31 H31A 1.10(3) . ? C31 H31B 0.98(3) . ? C32 C33 1.376(4) . ? C32 C37 1.388(4) . ? C33 C34 1.392(4) . ? C33 H33 0.99(3) . ? C34 C35 1.383(4) . ? C34 H34 1.05(2) . ? C35 C36 1.395(4) . ? C36 C37 1.382(4) . ? C36 H36 1.00(3) . ? C37 H37 0.97(3) . ? C39 C40 1.390(4) . ? C39 C44 1.405(4) . ? C40 C41 1.381(4) . ? C40 H40 0.92(3) . ? C41 C42 1.391(4) . ? C41 H41 0.95(3) . ? C42 C43 1.387(4) . ? C42 C45 1.525(4) . ? C43 C44 1.403(4) . ? C43 H43 0.99(3) . ? C44 C49 1.437(4) . ? C45 C48A 1.421(14) . ? C45 C47 1.488(6) . ? C45 C46 1.489(6) . ? C45 C46A 1.485(15) . ? C45 C48 1.549(6) . ? C45 C47A 1.668(14) . ? C46 H46A 0.9800 . ? C46 H46B 0.9800 . ? C46 H46C 0.9800 . ? C47 H47A 0.9800 . ? C47 H47B 0.9800 . ? C47 H47C 0.9800 . ? C48 H48A 0.9800 . ? C48 H48B 0.9800 . ? C48 H48C 0.9800 . ? C46A H46D 0.9800 . ? C46A H46E 0.9800 . ? C46A H46F 0.9800 . ? C47A H47D 0.9800 . ? C47A H47E 0.9800 . ? C47A H47F 0.9800 . ? C48A H48D 0.9800 . ? C48A H48E 0.9800 . ? C48A H48F 0.9800 . ? C49 C50 1.192(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 C22 O2 C25 119.4(2) . . ? C32 O3 C31 118.2(2) . . ? H1OA O5 H1OB 98(4) . . ? C5 N1 C1 117.0(2) . . ? C18 N2 C13 127.5(2) . . ? C18 N2 H2N 117.2(19) . . ? C13 N2 H2N 115.2(19) . . ? C18 N3 C19 124.9(2) . . ? C18 N3 H3N 115.0(17) . . ? C19 N3 H3N 119.9(17) . . ? C38 N4 C35 124.9(2) . . ? C38 N4 H4N 116.8(17) . . ? C35 N4 H4N 116.0(17) . . ? C38 N5 C39 126.4(3) . . ? C38 N5 H5N 122.3(19) . . ? C39 N5 H5N 110.0(19) . . ? N1 C1 C2 122.8(3) . . ? N1 C1 C50 117.7(2) . . ? C2 C1 C50 119.4(3) . . ? C3 C2 C1 119.0(3) . . ? C3 C2 H2 122.1(17) . . ? C1 C2 H2 118.9(17) . . ? C4 C3 C2 119.0(3) . . ? C4 C3 H3 117.7(16) . . ? C2 C3 H3 123.1(16) . . ? C3 C4 C5 119.2(3) . . ? C3 C4 H4 120.6(18) . . ? C5 C4 H4 120.2(18) . . ? N1 C5 C4 123.0(3) . . ? N1 C5 C6 116.9(2) . . ? C4 C5 C6 120.0(3) . . ? C7 C6 C5 174.0(3) . . ? C6 C7 C8 178.4(3) . . ? C9 C8 C13 120.4(3) . . ? C9 C8 C7 119.6(2) . . ? C13 C8 C7 120.0(2) . . ? C10 C9 C8 122.1(3) . . ? C10 C9 H9 114.2(19) . . ? C8 C9 H9 123.7(19) . . ? C9 C10 C11 116.5(3) . . ? C9 C10 C14 122.3(3) . . ? C11 C10 C14 121.1(3) . . ? C12 C11 C10 122.4(3) . . ? C12 C11 H11 122.0(15) . . ? C10 C11 H11 115.5(15) . . ? C11 C12 C13 121.1(3) . . ? C11 C12 H12 120.6(18) . . ? C13 C12 H12 118.2(18) . . ? C12 C13 N2 124.0(3) . . ? C12 C13 C8 117.4(3) . . ? N2 C13 C8 118.6(2) . . ? C17 C14 C15 111.4(4) . . ? C17 C14 C16 109.8(4) . . ? C15 C14 C16 104.6(4) . . ? C17 C14 C10 110.6(3) . . ? C15 C14 C10 111.9(3) . . ? C16 C14 C10 108.4(3) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O1 C18 N3 123.0(2) . . ? O1 C18 N2 122.1(3) . . ? N3 C18 N2 114.8(2) . . ? C20 C19 C24 118.6(3) . . ? C20 C19 N3 120.4(2) . . ? C24 C19 N3 121.0(3) . . ? C21 C20 C19 120.8(3) . . ? C21 C20 H20 120.8(16) . . ? C19 C20 H20 118.4(16) . . ? C22 C21 C20 119.6(3) . . ? C22 C21 H21 118.3(16) . . ? C20 C21 H21 122.0(16) . . ? C23 C22 O2 115.1(3) . . ? C23 C22 C21 119.9(3) . . ? O2 C22 C21 125.0(3) . . ? C22 C23 C24 120.7(3) . . ? C22 C23 H23 117(2) . . ? C24 C23 H23 123(2) . . ? C23 C24 C19 120.3(3) . . ? C23 C24 H24 121.1(16) . . ? C19 C24 H24 118.5(16) . . ? O2 C25 C26 106.9(3) . . ? O2 C25 H25A 107.5(17) . . ? C26 C25 H25A 111.8(17) . . ? O2 C25 H25B 109.3(17) . . ? C26 C25 H25B 110.9(16) . . ? H25A C25 H25B 110(2) . . ? C27 C26 C25 114.9(3) . . ? C27 C26 H26A 109(2) . . ? C25 C26 H26A 109(2) . . ? C27 C26 H26B 115.0(18) . . ? C25 C26 H26B 105.3(18) . . ? H26A C26 H26B 103(3) . . ? C26 C27 C28 114.9(3) . . ? C26 C27 H27A 109.2(16) . . ? C28 C27 H27A 108.8(16) . . ? C26 C27 H27B 109.3(17) . . ? C28 C27 H27B 108.0(17) . . ? H27A C27 H27B 106(2) . . ? C29 C28 C27 114.0(3) . . ? C29 C28 H28A 108.7(19) . . ? C27 C28 H28A 107.5(19) . . ? C29 C28 H28B 114.3(15) . . ? C27 C28 H28B 105.5(15) . . ? H28A C28 H28B 106(2) . . ? C28 C29 C30 114.6(3) . . ? C28 C29 H29A 109.5(16) . . ? C30 C29 H29A 107.8(15) . . ? C28 C29 H29B 114.2(19) . . ? C30 C29 H29B 107.2(19) . . ? H29A C29 H29B 103(2) . . ? C31 C30 C29 113.4(3) . . ? C31 C30 H30A 103(2) . . ? C29 C30 H30A 111(2) . . ? C31 C30 H30B 106.5(16) . . ? C29 C30 H30B 114.0(17) . . ? H30A C30 H30B 108(3) . . ? O3 C31 C30 106.6(3) . . ? O3 C31 H31A 111.0(14) . . ? C30 C31 H31A 111.0(14) . . ? O3 C31 H31B 102.5(15) . . ? C30 C31 H31B 117.0(15) . . ? H31A C31 H31B 108(2) . . ? O3 C32 C33 125.0(3) . . ? O3 C32 C37 115.4(2) . . ? C33 C32 C37 119.6(3) . . ? C32 C33 C34 119.5(3) . . ? C32 C33 H33 119.9(18) . . ? C34 C33 H33 120.6(18) . . ? C35 C34 C33 121.3(3) . . ? C35 C34 H34 120.1(13) . . ? C33 C34 H34 118.3(13) . . ? C34 C35 C36 118.8(2) . . ? C34 C35 N4 118.1(2) . . ? C36 C35 N4 123.1(2) . . ? C37 C36 C35 119.7(3) . . ? C37 C36 H36 119.1(18) . . ? C35 C36 H36 121.2(18) . . ? C36 C37 C32 121.0(3) . . ? C36 C37 H37 117.3(18) . . ? C32 C37 H37 121.2(18) . . ? O4 C38 N4 123.5(3) . . ? O4 C38 N5 123.4(3) . . ? N4 C38 N5 113.1(3) . . ? C40 C39 N5 124.0(3) . . ? C40 C39 C44 117.7(3) . . ? N5 C39 C44 118.2(2) . . ? C41 C40 C39 120.7(3) . . ? C41 C40 H40 119(2) . . ? C39 C40 H40 120(2) . . ? C40 C41 C42 123.1(3) . . ? C40 C41 H41 118.5(19) . . ? C42 C41 H41 118.3(19) . . ? C43 C42 C41 115.9(3) . . ? C43 C42 C45 123.1(3) . . ? C41 C42 C45 121.0(3) . . ? C42 C43 C44 122.5(3) . . ? C42 C43 H43 120.1(15) . . ? C44 C43 H43 117.4(15) . . ? C43 C44 C39 120.0(3) . . ? C43 C44 C49 118.7(2) . . ? C39 C44 C49 121.3(2) . . ? C48A C45 C47 52.6(10) . . ? C48A C45 C46 127.8(7) . . ? C47 C45 C46 113.6(5) . . ? C48A C45 C46A 110.7(16) . . ? C47 C45 C46A 146.0(8) . . ? C46 C45 C46A 48.7(14) . . ? C48A C45 C42 117.8(7) . . ? C47 C45 C42 109.4(3) . . ? C46 C45 C42 114.1(3) . . ? C46A C45 C42 104.6(7) . . ? C48A C45 C48 54.4(11) . . ? C47 C45 C48 106.7(5) . . ? C46 C45 C48 104.1(4) . . ? C46A C45 C48 61.7(15) . . ? C42 C45 C48 108.4(3) . . ? C48A C45 C47A 110.4(12) . . ? C47 C45 C47A 62.9(8) . . ? C46 C45 C47A 59.2(8) . . ? C46A C45 C47A 107.8(17) . . ? C42 C45 C47A 104.8(6) . . ? C48 C45 C47A 146.7(6) . . ? C45 C46 H46A 109.5 . . ? C45 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? C45 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? C45 C47 H47A 109.5 . . ? C45 C47 H47B 109.5 . . ? H47A C47 H47B 109.5 . . ? C45 C47 H47C 109.5 . . ? H47A C47 H47C 109.5 . . ? H47B C47 H47C 109.5 . . ? C45 C48 H48A 109.5 . . ? C45 C48 H48B 109.5 . . ? H48A C48 H48B 109.5 . . ? C45 C48 H48C 109.5 . . ? H48A C48 H48C 109.5 . . ? H48B C48 H48C 109.5 . . ? C45 C46A H46D 109.5 . . ? C45 C46A H46E 109.5 . . ? H46D C46A H46E 109.5 . . ? C45 C46A H46F 109.5 . . ? H46D C46A H46F 109.5 . . ? H46E C46A H46F 109.5 . . ? C45 C47A H47D 109.5 . . ? C45 C47A H47E 109.5 . . ? H47D C47A H47E 109.5 . . ? C45 C47A H47F 109.5 . . ? H47D C47A H47F 109.5 . . ? H47E C47A H47F 109.5 . . ? C45 C48A H48D 109.5 . . ? C45 C48A H48E 109.5 . . ? H48D C48A H48E 109.5 . . ? C45 C48A H48F 109.5 . . ? H48D C48A H48F 109.5 . . ? H48E C48A H48F 109.5 . . ? C50 C49 C44 177.1(3) . . ? C49 C50 C1 173.1(3) . . ? 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 C5 N1 C1 C2 0.2(4) . . . . ? C5 N1 C1 C50 -175.4(2) . . . . ? N1 C1 C2 C3 0.0(4) . . . . ? C50 C1 C2 C3 175.5(3) . . . . ? C1 C2 C3 C4 0.0(4) . . . . ? C2 C3 C4 C5 -0.2(4) . . . . ? C1 N1 C5 C4 -0.4(4) . . . . ? C1 N1 C5 C6 175.8(2) . . . . ? C3 C4 C5 N1 0.4(4) . . . . ? C3 C4 C5 C6 -175.6(3) . . . . ? N1 C5 C6 C7 -112(3) . . . . ? C4 C5 C6 C7 65(3) . . . . ? C5 C6 C7 C8 37(14) . . . . ? C6 C7 C8 C9 -97(12) . . . . ? C6 C7 C8 C13 83(12) . . . . ? C13 C8 C9 C10 -1.6(4) . . . . ? C7 C8 C9 C10 177.9(3) . . . . ? C8 C9 C10 C11 1.9(4) . . . . ? C8 C9 C10 C14 178.9(3) . . . . ? C9 C10 C11 C12 -0.3(4) . . . . ? C14 C10 C11 C12 -177.3(3) . . . . ? C10 C11 C12 C13 -1.6(5) . . . . ? C11 C12 C13 N2 -180.0(3) . . . . ? C11 C12 C13 C8 1.9(4) . . . . ? C18 N2 C13 C12 11.4(4) . . . . ? C18 N2 C13 C8 -170.4(2) . . . . ? C9 C8 C13 C12 -0.3(4) . . . . ? C7 C8 C13 C12 -179.8(2) . . . . ? C9 C8 C13 N2 -178.6(2) . . . . ? C7 C8 C13 N2 1.9(4) . . . . ? C9 C10 C14 C17 139.1(4) . . . . ? C11 C10 C14 C17 -44.0(5) . . . . ? C9 C10 C14 C15 14.4(5) . . . . ? C11 C10 C14 C15 -168.8(4) . . . . ? C9 C10 C14 C16 -100.5(4) . . . . ? C11 C10 C14 C16 76.4(4) . . . . ? C19 N3 C18 O1 -10.5(4) . . . . ? C19 N3 C18 N2 170.2(2) . . . . ? C13 N2 C18 O1 13.4(4) . . . . ? C13 N2 C18 N3 -167.2(2) . . . . ? C18 N3 C19 C20 149.7(3) . . . . ? C18 N3 C19 C24 -31.8(4) . . . . ? C24 C19 C20 C21 1.0(4) . . . . ? N3 C19 C20 C21 179.5(2) . . . . ? C19 C20 C21 C22 1.9(4) . . . . ? C25 O2 C22 C23 178.1(3) . . . . ? C25 O2 C22 C21 -0.4(4) . . . . ? C20 C21 C22 C23 -2.9(4) . . . . ? C20 C21 C22 O2 175.6(3) . . . . ? O2 C22 C23 C24 -177.6(3) . . . . ? C21 C22 C23 C24 1.0(4) . . . . ? C22 C23 C24 C19 1.9(4) . . . . ? C20 C19 C24 C23 -2.9(4) . . . . ? N3 C19 C24 C23 178.6(3) . . . . ? C22 O2 C25 C26 179.1(2) . . . . ? O2 C25 C26 C27 -53.7(4) . . . . ? C25 C26 C27 C28 -48.3(5) . . . . ? C26 C27 C28 C29 -61.3(4) . . . . ? C27 C28 C29 C30 170.7(3) . . . . ? C28 C29 C30 C31 -63.2(4) . . . . ? C32 O3 C31 C30 174.9(2) . . . . ? C29 C30 C31 O3 -56.4(4) . . . . ? C31 O3 C32 C33 4.6(4) . . . . ? C31 O3 C32 C37 -174.9(3) . . . . ? O3 C32 C33 C34 179.4(3) . . . . ? C37 C32 C33 C34 -1.1(4) . . . . ? C32 C33 C34 C35 0.7(4) . . . . ? C33 C34 C35 C36 0.7(4) . . . . ? C33 C34 C35 N4 180.0(3) . . . . ? C38 N4 C35 C34 151.4(3) . . . . ? C38 N4 C35 C36 -29.4(4) . . . . ? C34 C35 C36 C37 -1.7(4) . . . . ? N4 C35 C36 C37 179.1(3) . . . . ? C35 C36 C37 C32 1.3(4) . . . . ? O3 C32 C37 C36 179.6(3) . . . . ? C33 C32 C37 C36 0.1(4) . . . . ? C35 N4 C38 O4 7.6(5) . . . . ? C35 N4 C38 N5 -173.6(2) . . . . ? C39 N5 C38 O4 -10.1(5) . . . . ? C39 N5 C38 N4 171.1(3) . . . . ? C38 N5 C39 C40 -1.4(5) . . . . ? C38 N5 C39 C44 178.3(3) . . . . ? N5 C39 C40 C41 -179.9(3) . . . . ? C44 C39 C40 C41 0.3(5) . . . . ? C39 C40 C41 C42 -0.7(5) . . . . ? C40 C41 C42 C43 0.6(5) . . . . ? C40 C41 C42 C45 -179.1(3) . . . . ? C41 C42 C43 C44 -0.2(5) . . . . ? C45 C42 C43 C44 179.5(3) . . . . ? C42 C43 C44 C39 -0.1(4) . . . . ? C42 C43 C44 C49 -178.4(3) . . . . ? C40 C39 C44 C43 0.0(4) . . . . ? N5 C39 C44 C43 -179.7(3) . . . . ? C40 C39 C44 C49 178.3(3) . . . . ? N5 C39 C44 C49 -1.5(4) . . . . ? C43 C42 C45 C48A -175.6(14) . . . . ? C41 C42 C45 C48A 4.1(14) . . . . ? C43 C42 C45 C47 127.2(5) . . . . ? C41 C42 C45 C47 -53.1(6) . . . . ? C43 C42 C45 C46 -1.2(5) . . . . ? C41 C42 C45 C46 178.4(4) . . . . ? C43 C42 C45 C46A -52.1(17) . . . . ? C41 C42 C45 C46A 127.5(17) . . . . ? C43 C42 C45 C48 -116.7(4) . . . . ? C41 C42 C45 C48 62.9(5) . . . . ? C43 C42 C45 C47A 61.2(9) . . . . ? C41 C42 C45 C47A -119.1(9) . . . . ? C43 C44 C49 C50 33(6) . . . . ? C39 C44 C49 C50 -146(6) . . . . ? C44 C49 C50 C1 -14(8) . . . . ? N1 C1 C50 C49 135(2) . . . . ? C2 C1 C50 C49 -41(3) . . . . ? 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 O5 H1OA N1 1.07(4) 1.90(4) 2.959(3) 173(3) . O5 H1OB O1 0.74(4) 2.22(4) 2.943(3) 168(5) 8_665 N2 H2N O5 0.88(3) 2.53(3) 3.253(4) 139(2) . N3 H3N O5 0.92(3) 2.01(3) 2.900(3) 160(2) . N4 H4N O1 0.89(3) 2.04(3) 2.924(3) 169(2) 8_665 N5 H5N O1 0.90(3) 2.59(3) 3.313(3) 138(2) 8_665 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.309 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.064 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.750 -0.024 0.132 745.5 55.6 2 0.250 -0.031 0.368 745.5 55.8 3 0.750 -0.040 0.632 745.4 55.7 4 0.250 -0.034 0.868 745.4 55.8 _platon_squeeze_details ; ? ; _database_code_depnum_ccdc_archive 'CCDC 968268'