# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_01211chl _database_code_depnum_ccdc_archive 'CCDC 872113' #TrackingRef '10201_web_deposit_cif_file_0_chang-heeLee_1332160289.01211CHL.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C54 H68 N4 O4, C O ' _chemical_formula_sum 'C55 H68 N4 O5' _chemical_formula_weight 865.13 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' O O 0.0492 0.0322 '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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P ccn' _symmetry_space_group_name_Hall '-P 2ab 2ac' _symmetry_Int_Tables_number 56 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' 'x+1/2, -y, -z+1/2' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' '-x-1/2, y, z-1/2' 'x, -y-1/2, z-1/2' _cell_length_a 34.4374(8) _cell_length_b 10.2869(2) _cell_length_c 13.5539(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4801.52(18) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 26811 _cell_measurement_theta_min 3.26 _cell_measurement_theta_max 68.18 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.197 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1864 _exptl_absorpt_coefficient_mu 0.600 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9424 _exptl_absorpt_correction_T_max 0.9706 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 1.54187 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 47801 _diffrn_reflns_av_R_equivalents 0.0676 _diffrn_reflns_av_sigmaI/netI 0.0502 _diffrn_reflns_limit_h_min -41 _diffrn_reflns_limit_h_max 41 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 5.14 _diffrn_reflns_theta_max 68.24 _reflns_number_total 4347 _reflns_number_gt 2512 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0943P)^2^+0.7386P] 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 4347 _refine_ls_number_parameters 299 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1136 _refine_ls_R_factor_gt 0.0642 _refine_ls_wR_factor_ref 0.2029 _refine_ls_wR_factor_gt 0.1634 _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_restrained_S_all 1.102 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.49360(6) 0.33046(19) 0.52947(15) 0.0666(6) Uani 1 1 d . . . O2 O 0.55637(6) -0.07629(19) 0.61374(15) 0.0684(6) Uani 1 1 d . . . N2 N 0.73255(7) 0.4667(2) 0.34975(19) 0.0684(7) Uani 1 1 d . . . H1 H 0.7375 0.4310 0.2921 0.082 Uiso 1 1 calc R . . N1 N 0.68343(7) 0.1849(2) 0.36890(19) 0.0640(7) Uani 1 1 d . . . H2 H 0.6943 0.2011 0.4264 0.077 Uiso 1 1 calc R . . C22 C 0.75985(8) 0.5288(3) 0.4078(2) 0.0655(8) Uani 1 1 d . . . C16 C 0.66075(8) 0.4167(3) 0.3439(2) 0.0620(8) Uani 1 1 d . . . C1 C 0.47001(8) 0.1973(3) 0.6562(2) 0.0645(8) Uani 1 1 d . . . H3 H 0.4505 0.2608 0.6680 0.077 Uiso 1 1 calc R . . C12 C 0.51839(8) 0.3463(3) 0.4444(2) 0.0662(8) Uani 1 1 d . . . H10 H 0.5064 0.4098 0.3988 0.079 Uiso 1 1 calc R . . H11 H 0.5204 0.2622 0.4093 0.079 Uiso 1 1 calc R . . C23 C 0.69662(8) 0.4681(3) 0.3942(2) 0.0630(8) Uani 1 1 d . . . C13 C 0.55856(8) 0.3923(3) 0.4710(2) 0.0610(8) Uani 1 1 d . . . H12 H 0.5680 0.3419 0.5284 0.073 Uiso 1 1 calc R . . H13 H 0.5572 0.4848 0.4909 0.073 Uiso 1 1 calc R . . C2 C 0.52801(9) 0.0165(3) 0.6246(2) 0.0630(8) Uani 1 1 d . . . C18 C 0.66543(8) 0.2771(3) 0.3112(2) 0.0611(7) Uani 1 1 d . . . C14 C 0.62711(8) 0.4255(3) 0.4200(2) 0.0639(8) Uani 1 1 d . . . H14 H 0.6347 0.3750 0.4791 0.077 Uiso 1 1 calc R . . H15 H 0.6246 0.5175 0.4406 0.077 Uiso 1 1 calc R . . C19 C 0.68233(8) 0.0632(3) 0.3249(2) 0.0623(8) Uani 1 1 d . . . C15 C 0.58756(8) 0.3784(3) 0.3868(2) 0.0652(8) Uani 1 1 d . . . H16 H 0.5892 0.2862 0.3664 0.078 Uiso 1 1 calc R . . H17 H 0.5787 0.4301 0.3294 0.078 Uiso 1 1 calc R . . C3 C 0.47060(9) 0.0842(3) 0.7120(2) 0.0665(8) Uani 1 1 d . . . C4 C 0.50000(9) -0.0060(3) 0.6959(2) 0.0658(8) Uani 1 1 d . . . H4 H 0.5009 -0.0835 0.7340 0.079 Uiso 1 1 calc R . . C26 C 0.70172(9) -0.1659(3) 0.2949(2) 0.0715(9) Uani 1 1 d . . . H18 H 0.6757 -0.1830 0.2684 0.107 Uiso 1 1 calc R . . H19 H 0.7118 -0.2446 0.3266 0.107 Uiso 1 1 calc R . . H20 H 0.7191 -0.1402 0.2411 0.107 Uiso 1 1 calc R . . C8 C 0.58350(9) -0.0571(3) 0.5342(2) 0.0651(8) Uani 1 1 d . . . H21 H 0.6006 0.0178 0.5491 0.078 Uiso 1 1 calc R . . H22 H 0.5692 -0.0379 0.4724 0.078 Uiso 1 1 calc R . . C27 C 0.69943(8) -0.0545(3) 0.3720(2) 0.0645(8) Uani 1 1 d . . . C20 C 0.66257(9) 0.0805(3) 0.2379(2) 0.0653(8) Uani 1 1 d . . . H5 H 0.6569 0.0145 0.1910 0.078 Uiso 1 1 calc R . . C9 C 0.60750(9) -0.1776(3) 0.5212(2) 0.0668(8) Uani 1 1 d . . . H23 H 0.5902 -0.2530 0.5093 0.080 Uiso 1 1 calc R . . H24 H 0.6225 -0.1946 0.5822 0.080 Uiso 1 1 calc R . . C10 C 0.63561(8) -0.1614(3) 0.4336(2) 0.0657(8) Uani 1 1 d . . . H25 H 0.6407 -0.2480 0.4044 0.079 Uiso 1 1 calc R . . H26 H 0.6229 -0.1075 0.3824 0.079 Uiso 1 1 calc R . . C24 C 0.70128(9) 0.5329(3) 0.4820(2) 0.0712(9) Uani 1 1 d . . . H6 H 0.6814 0.5492 0.5290 0.085 Uiso 1 1 calc R . . C21 C 0.65208(9) 0.2130(3) 0.2296(2) 0.0674(8) Uani 1 1 d . . . H7 H 0.6382 0.2510 0.1764 0.081 Uiso 1 1 calc R . . C5 C 0.49752(9) 0.2185(3) 0.5836(2) 0.0630(8) Uani 1 1 d . . . C25 C 0.74047(9) 0.5713(3) 0.4908(2) 0.0710(9) Uani 1 1 d . . . H8 H 0.7515 0.6181 0.5443 0.085 Uiso 1 1 calc R . . C17 C 0.65148(9) 0.5017(3) 0.2537(2) 0.0706(9) Uani 1 1 d . . . H27 H 0.6476 0.5918 0.2749 0.106 Uiso 1 1 calc R . . H28 H 0.6278 0.4697 0.2217 0.106 Uiso 1 1 calc R . . H29 H 0.6731 0.4978 0.2069 0.106 Uiso 1 1 calc R . . C28 C 0.67403(8) -0.0993(3) 0.4613(2) 0.0658(8) Uani 1 1 d . . . H30 H 0.6892 -0.1623 0.5009 0.079 Uiso 1 1 calc R . . H31 H 0.6687 -0.0229 0.5037 0.079 Uiso 1 1 calc R . . C6 C 0.43908(9) 0.0583(4) 0.7861(2) 0.0792(10) Uani 1 1 d . . . H32 H 0.4370 0.1324 0.8312 0.119 Uiso 1 1 calc R . . H33 H 0.4454 -0.0202 0.8237 0.119 Uiso 1 1 calc R . . H34 H 0.4143 0.0459 0.7517 0.119 Uiso 1 1 calc R . . C7 C 0.52691(9) 0.1278(3) 0.5673(2) 0.0630(8) Uani 1 1 d . . . H9 H 0.5459 0.1421 0.5177 0.076 Uiso 1 1 calc R . . O3 O 0.7500 0.2500 0.1969(4) 0.126(3) Uani 0.732(10) 2 d SP A 1 C31 C 0.7500 0.2500 0.1048(7) 0.122(2) Uani 1 2 d S . . O4 O 0.7500 0.2500 0.0189(11) 0.114(7) Uani 0.268(10) 2 d SP A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0593(12) 0.0572(13) 0.0833(14) 0.0055(11) 0.0071(10) 0.0006(10) O2 0.0678(14) 0.0598(13) 0.0777(13) 0.0050(10) 0.0057(11) 0.0054(10) N2 0.0573(15) 0.0701(17) 0.0776(17) -0.0114(13) 0.0023(12) -0.0093(13) N1 0.0617(15) 0.0607(16) 0.0694(16) -0.0011(13) -0.0042(12) -0.0036(12) C22 0.0568(18) 0.0601(19) 0.080(2) -0.0055(16) 0.0012(15) -0.0100(15) C16 0.0562(18) 0.0568(19) 0.073(2) 0.0002(15) 0.0002(14) -0.0024(14) C1 0.0525(17) 0.065(2) 0.076(2) -0.0026(16) 0.0021(14) -0.0010(14) C12 0.0607(19) 0.063(2) 0.075(2) 0.0042(15) 0.0064(15) 0.0007(15) C23 0.0522(18) 0.0626(19) 0.0741(19) -0.0020(16) 0.0044(14) -0.0052(14) C13 0.0540(18) 0.0545(18) 0.0745(19) -0.0017(14) 0.0032(14) 0.0016(14) C2 0.0617(18) 0.0564(19) 0.0709(19) -0.0002(15) -0.0023(15) -0.0001(15) C18 0.0529(17) 0.0551(19) 0.075(2) -0.0002(15) 0.0005(14) -0.0028(14) C14 0.0580(18) 0.0560(19) 0.078(2) -0.0049(15) 0.0032(15) -0.0029(14) C19 0.0608(19) 0.0530(19) 0.073(2) 0.0005(15) 0.0023(15) -0.0052(14) C15 0.0582(18) 0.0619(19) 0.075(2) -0.0034(16) 0.0020(15) -0.0025(14) C3 0.0589(19) 0.071(2) 0.069(2) -0.0009(16) -0.0016(15) -0.0072(16) C4 0.064(2) 0.065(2) 0.068(2) 0.0050(15) -0.0029(15) -0.0063(16) C26 0.067(2) 0.064(2) 0.083(2) -0.0062(17) 0.0043(17) -0.0047(16) C8 0.0656(19) 0.059(2) 0.0708(19) 0.0038(15) 0.0045(15) -0.0023(15) C27 0.0556(18) 0.0607(19) 0.077(2) 0.0014(15) -0.0019(15) -0.0057(14) C20 0.069(2) 0.059(2) 0.068(2) -0.0026(15) 0.0013(15) -0.0022(15) C9 0.0598(18) 0.060(2) 0.081(2) 0.0002(15) 0.0011(16) -0.0056(15) C10 0.0603(19) 0.0568(19) 0.080(2) 0.0012(15) 0.0030(15) -0.0071(14) C24 0.0585(19) 0.075(2) 0.080(2) -0.0051(17) 0.0077(16) -0.0085(16) C21 0.0630(19) 0.069(2) 0.070(2) -0.0032(16) -0.0040(15) 0.0006(16) C5 0.0586(19) 0.0545(19) 0.076(2) 0.0019(15) -0.0009(15) -0.0065(15) C25 0.065(2) 0.074(2) 0.074(2) -0.0067(16) -0.0006(16) -0.0139(17) C17 0.0695(19) 0.064(2) 0.078(2) 0.0038(17) 0.0028(16) -0.0059(16) C28 0.0601(19) 0.0597(19) 0.078(2) 0.0055(16) 0.0000(15) -0.0063(14) C6 0.063(2) 0.097(3) 0.077(2) 0.0119(19) 0.0044(16) -0.0061(18) C7 0.0572(18) 0.0587(19) 0.0730(19) -0.0016(15) 0.0029(15) -0.0012(15) O3 0.157(5) 0.152(6) 0.070(4) 0.000 0.000 0.071(4) C31 0.136(6) 0.143(6) 0.085(5) 0.000 0.000 -0.001(5) O4 0.140(13) 0.140(14) 0.062(10) 0.000 0.000 0.052(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C5 1.372(3) . ? O1 C12 1.444(3) . ? O2 C2 1.374(3) . ? O2 C8 1.441(3) . ? N2 C23 1.376(3) . ? N2 C22 1.382(4) . ? N2 H1 0.8800 . ? N1 C18 1.377(4) . ? N1 C19 1.387(4) . ? N1 H2 0.8800 . ? C22 C25 1.379(4) . ? C22 C27 1.507(4) 2_655 ? C16 C23 1.507(4) . ? C16 C18 1.511(4) . ? C16 C17 1.537(4) . ? C16 C14 1.553(4) . ? C1 C5 1.384(4) . ? C1 C3 1.387(4) . ? C1 H3 0.9500 . ? C12 C13 1.506(4) . ? C12 H10 0.9900 . ? C12 H11 0.9900 . ? C23 C24 1.374(4) . ? C13 C15 1.523(4) . ? C13 H12 0.9900 . ? C13 H13 0.9900 . ? C2 C7 1.384(4) . ? C2 C4 1.385(4) . ? C18 C21 1.367(4) . ? C14 C15 1.514(4) . ? C14 H14 0.9900 . ? C14 H15 0.9900 . ? C19 C20 1.373(4) . ? C19 C27 1.490(4) . ? C15 H16 0.9900 . ? C15 H17 0.9900 . ? C3 C4 1.391(4) . ? C3 C6 1.503(4) . ? C4 H4 0.9500 . ? C26 C27 1.552(4) . ? C26 H18 0.9800 . ? C26 H19 0.9800 . ? C26 H20 0.9800 . ? C8 C9 1.501(4) . ? C8 H21 0.9900 . ? C8 H22 0.9900 . ? C27 C22 1.507(4) 2_655 ? C27 C28 1.563(4) . ? C20 C21 1.415(4) . ? C20 H5 0.9500 . ? C9 C10 1.542(4) . ? C9 H23 0.9900 . ? C9 H24 0.9900 . ? C10 C28 1.517(4) . ? C10 H25 0.9900 . ? C10 H26 0.9900 . ? C24 C25 1.411(4) . ? C24 H6 0.9500 . ? C21 H7 0.9500 . ? C5 C7 1.394(4) . ? C25 H8 0.9500 . ? C17 H27 0.9800 . ? C17 H28 0.9800 . ? C17 H29 0.9800 . ? C28 H30 0.9900 . ? C28 H31 0.9900 . ? C6 H32 0.9800 . ? C6 H33 0.9800 . ? C6 H34 0.9800 . ? C7 H9 0.9500 . ? O3 C31 1.249(8) . ? C31 O4 1.164(13) . ? 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 C5 O1 C12 117.6(2) . . ? C2 O2 C8 116.5(2) . . ? C23 N2 C22 110.9(3) . . ? C23 N2 H1 124.5 . . ? C22 N2 H1 124.5 . . ? C18 N1 C19 111.4(3) . . ? C18 N1 H2 124.3 . . ? C19 N1 H2 124.3 . . ? C25 C22 N2 106.4(3) . . ? C25 C22 C27 131.1(3) . 2_655 ? N2 C22 C27 122.0(3) . 2_655 ? C23 C16 C18 112.2(2) . . ? C23 C16 C17 109.3(2) . . ? C18 C16 C17 109.3(2) . . ? C23 C16 C14 106.9(2) . . ? C18 C16 C14 109.2(2) . . ? C17 C16 C14 109.9(2) . . ? C5 C1 C3 120.7(3) . . ? C5 C1 H3 119.7 . . ? C3 C1 H3 119.7 . . ? O1 C12 C13 112.8(2) . . ? O1 C12 H10 109.0 . . ? C13 C12 H10 109.0 . . ? O1 C12 H11 109.0 . . ? C13 C12 H11 109.0 . . ? H10 C12 H11 107.8 . . ? C24 C23 N2 106.2(3) . . ? C24 C23 C16 131.1(3) . . ? N2 C23 C16 122.4(3) . . ? C12 C13 C15 113.2(2) . . ? C12 C13 H12 108.9 . . ? C15 C13 H12 108.9 . . ? C12 C13 H13 108.9 . . ? C15 C13 H13 108.9 . . ? H12 C13 H13 107.8 . . ? O2 C2 C7 122.3(3) . . ? O2 C2 C4 117.0(3) . . ? C7 C2 C4 120.7(3) . . ? C21 C18 N1 106.2(3) . . ? C21 C18 C16 131.2(3) . . ? N1 C18 C16 122.4(3) . . ? C15 C14 C16 117.1(2) . . ? C15 C14 H14 108.0 . . ? C16 C14 H14 108.0 . . ? C15 C14 H15 108.0 . . ? C16 C14 H15 108.0 . . ? H14 C14 H15 107.3 . . ? C20 C19 N1 105.4(3) . . ? C20 C19 C27 132.0(3) . . ? N1 C19 C27 122.6(3) . . ? C14 C15 C13 109.7(2) . . ? C14 C15 H16 109.7 . . ? C13 C15 H16 109.7 . . ? C14 C15 H17 109.7 . . ? C13 C15 H17 109.7 . . ? H16 C15 H17 108.2 . . ? C1 C3 C4 119.0(3) . . ? C1 C3 C6 120.2(3) . . ? C4 C3 C6 120.8(3) . . ? C2 C4 C3 120.3(3) . . ? C2 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C27 C26 H18 109.5 . . ? C27 C26 H19 109.5 . . ? H18 C26 H19 109.5 . . ? C27 C26 H20 109.5 . . ? H18 C26 H20 109.5 . . ? H19 C26 H20 109.5 . . ? O2 C8 C9 109.3(2) . . ? O2 C8 H21 109.8 . . ? C9 C8 H21 109.8 . . ? O2 C8 H22 109.8 . . ? C9 C8 H22 109.8 . . ? H21 C8 H22 108.3 . . ? C19 C27 C22 111.3(2) . 2_655 ? C19 C27 C26 109.4(3) . . ? C22 C27 C26 107.4(2) 2_655 . ? C19 C27 C28 110.5(3) . . ? C22 C27 C28 108.8(2) 2_655 . ? C26 C27 C28 109.4(2) . . ? C19 C20 C21 108.6(3) . . ? C19 C20 H5 125.7 . . ? C21 C20 H5 125.7 . . ? C8 C9 C10 110.3(2) . . ? C8 C9 H23 109.6 . . ? C10 C9 H23 109.6 . . ? C8 C9 H24 109.6 . . ? C10 C9 H24 109.6 . . ? H23 C9 H24 108.1 . . ? C28 C10 C9 113.7(3) . . ? C28 C10 H25 108.8 . . ? C9 C10 H25 108.8 . . ? C28 C10 H26 108.8 . . ? C9 C10 H26 108.8 . . ? H25 C10 H26 107.7 . . ? C23 C24 C25 108.7(3) . . ? C23 C24 H6 125.6 . . ? C25 C24 H6 125.6 . . ? C18 C21 C20 108.4(3) . . ? C18 C21 H7 125.8 . . ? C20 C21 H7 125.8 . . ? O1 C5 C1 116.4(3) . . ? O1 C5 C7 123.3(3) . . ? C1 C5 C7 120.3(3) . . ? C22 C25 C24 107.7(3) . . ? C22 C25 H8 126.1 . . ? C24 C25 H8 126.1 . . ? C16 C17 H27 109.5 . . ? C16 C17 H28 109.5 . . ? H27 C17 H28 109.5 . . ? C16 C17 H29 109.5 . . ? H27 C17 H29 109.5 . . ? H28 C17 H29 109.5 . . ? C10 C28 C27 114.9(2) . . ? C10 C28 H30 108.6 . . ? C27 C28 H30 108.6 . . ? C10 C28 H31 108.6 . . ? C27 C28 H31 108.6 . . ? H30 C28 H31 107.5 . . ? C3 C6 H32 109.5 . . ? C3 C6 H33 109.5 . . ? H32 C6 H33 109.5 . . ? C3 C6 H34 109.5 . . ? H32 C6 H34 109.5 . . ? H33 C6 H34 109.5 . . ? C2 C7 C5 119.0(3) . . ? C2 C7 H9 120.5 . . ? C5 C7 H9 120.5 . . ? O4 C31 O3 180.000(2) . . ? 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 C23 N2 C22 C25 -0.4(4) . . . . ? C23 N2 C22 C27 -173.1(3) . . . 2_655 ? C5 O1 C12 C13 -80.6(3) . . . . ? C22 N2 C23 C24 0.2(4) . . . . ? C22 N2 C23 C16 175.0(3) . . . . ? C18 C16 C23 C24 -130.6(4) . . . . ? C17 C16 C23 C24 108.0(4) . . . . ? C14 C16 C23 C24 -10.9(4) . . . . ? C18 C16 C23 N2 56.0(4) . . . . ? C17 C16 C23 N2 -65.3(4) . . . . ? C14 C16 C23 N2 175.8(3) . . . . ? O1 C12 C13 C15 166.1(2) . . . . ? C8 O2 C2 C7 -4.6(4) . . . . ? C8 O2 C2 C4 175.1(2) . . . . ? C19 N1 C18 C21 0.9(3) . . . . ? C19 N1 C18 C16 177.0(3) . . . . ? C23 C16 C18 C21 -143.8(3) . . . . ? C17 C16 C18 C21 -22.3(4) . . . . ? C14 C16 C18 C21 97.9(4) . . . . ? C23 C16 C18 N1 41.2(4) . . . . ? C17 C16 C18 N1 162.7(3) . . . . ? C14 C16 C18 N1 -77.1(3) . . . . ? C23 C16 C14 C15 -179.7(3) . . . . ? C18 C16 C14 C15 -58.0(3) . . . . ? C17 C16 C14 C15 61.8(3) . . . . ? C18 N1 C19 C20 -0.8(3) . . . . ? C18 N1 C19 C27 -179.5(3) . . . . ? C16 C14 C15 C13 179.1(2) . . . . ? C12 C13 C15 C14 -179.5(3) . . . . ? C5 C1 C3 C4 1.9(4) . . . . ? C5 C1 C3 C6 -176.0(3) . . . . ? O2 C2 C4 C3 179.3(3) . . . . ? C7 C2 C4 C3 -1.0(4) . . . . ? C1 C3 C4 C2 -0.6(4) . . . . ? C6 C3 C4 C2 177.4(3) . . . . ? C2 O2 C8 C9 -169.7(2) . . . . ? C20 C19 C27 C22 133.0(3) . . . 2_655 ? N1 C19 C27 C22 -48.8(4) . . . 2_655 ? C20 C19 C27 C26 14.5(4) . . . . ? N1 C19 C27 C26 -167.3(3) . . . . ? C20 C19 C27 C28 -106.0(4) . . . . ? N1 C19 C27 C28 72.3(3) . . . . ? N1 C19 C20 C21 0.4(3) . . . . ? C27 C19 C20 C21 178.9(3) . . . . ? O2 C8 C9 C10 177.6(2) . . . . ? C8 C9 C10 C28 87.6(3) . . . . ? N2 C23 C24 C25 0.1(4) . . . . ? C16 C23 C24 C25 -174.1(3) . . . . ? N1 C18 C21 C20 -0.6(3) . . . . ? C16 C18 C21 C20 -176.2(3) . . . . ? C19 C20 C21 C18 0.1(3) . . . . ? C12 O1 C5 C1 -171.4(2) . . . . ? C12 O1 C5 C7 7.7(4) . . . . ? C3 C1 C5 O1 177.3(3) . . . . ? C3 C1 C5 C7 -1.8(4) . . . . ? N2 C22 C25 C24 0.4(4) . . . . ? C27 C22 C25 C24 172.2(3) 2_655 . . . ? C23 C24 C25 C22 -0.3(4) . . . . ? C9 C10 C28 C27 -167.5(3) . . . . ? C19 C27 C28 C10 72.5(3) . . . . ? C22 C27 C28 C10 -165.0(3) 2_655 . . . ? C26 C27 C28 C10 -48.0(3) . . . . ? O2 C2 C7 C5 -179.1(3) . . . . ? C4 C2 C7 C5 1.2(4) . . . . ? O1 C5 C7 C2 -178.8(3) . . . . ? C1 C5 C7 C2 0.2(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 N2 H1 O3 0.88 2.31 3.101(4) 150.4 . N1 H2 O4 0.88 2.35 3.136(10) 149.3 7_756 N2 H1 O3 0.88 2.31 3.101(4) 150.4 . N2 H1 O3 0.88 2.31 3.101(4) 150.4 . N2 H1 O3 0.88 2.31 3.101(4) 150.4 . N2 H1 O3 0.88 2.31 3.101(4) 150.4 . _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 68.24 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.286 _refine_diff_density_min -0.257 _refine_diff_density_rms 0.044 data_01130chl _database_code_depnum_ccdc_archive 'CCDC 872114' #TrackingRef '10202_web_deposit_cif_file_1_chang-heeLee_1332160289.01130CHL.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C54 H68 N4 O4, C H4 O, C Cl3 ' _chemical_formula_sum 'C56 H72 Cl3 N4 O5' _chemical_formula_weight 987.53 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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.7904(6) _cell_length_b 12.5321(6) _cell_length_c 19.6483(10) _cell_angle_alpha 72.935(3) _cell_angle_beta 78.389(3) _cell_angle_gamma 68.038(3) _cell_volume 2560.2(2) _cell_formula_units_Z 2 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 10855 _cell_measurement_theta_min 3.92 _cell_measurement_theta_max 68.01 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.281 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1054 _exptl_absorpt_coefficient_mu 2.032 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6867 _exptl_absorpt_correction_T_max 0.9052 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 1.54187 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21173 _diffrn_reflns_av_R_equivalents 0.1997 _diffrn_reflns_av_sigmaI/netI 0.2561 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.92 _diffrn_reflns_theta_max 60.00 _reflns_number_total 7406 _reflns_number_gt 2185 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.1254P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7406 _refine_ls_number_parameters 621 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.2272 _refine_ls_R_factor_gt 0.1251 _refine_ls_wR_factor_ref 0.3635 _refine_ls_wR_factor_gt 0.2857 _refine_ls_goodness_of_fit_ref 0.894 _refine_ls_restrained_S_all 0.894 _refine_ls_shift/su_max 0.011 _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 -0.2428(3) -0.0155(2) 0.55185(15) 0.1043(10) Uani 1 1 d . . . Cl2 Cl -0.4853(3) 0.1241(3) 0.50871(17) 0.1251(12) Uani 1 1 d . . . O1 O 0.3331(6) 0.5519(5) -0.2895(3) 0.0804(18) Uani 1 1 d . . . O2 O -0.0349(6) 0.1906(5) 0.2713(3) 0.0773(17) Uani 1 1 d . . . O3 O 0.2653(6) 0.3570(5) 0.2562(3) 0.0752(18) Uani 1 1 d . . . O4 O 0.0311(6) 0.3701(5) -0.2814(4) 0.0838(19) Uani 1 1 d . . . C1 C 0.1817(9) 0.4579(7) -0.2794(5) 0.072(3) Uani 1 1 d . . . H1 H 0.1568 0.4607 -0.2307 0.087 Uiso 1 1 calc R . . N1 N 0.4414(7) 0.1906(6) 0.1592(4) 0.071(2) Uani 1 1 d . . . H65 H 0.3730 0.2174 0.1863 0.085 Uiso 1 1 calc R . . C2 C 0.0183(9) 0.2359(8) 0.3060(5) 0.072(3) Uani 1 1 d . . . N2 N 0.1345(7) 0.0162(6) 0.1680(4) 0.076(2) Uani 1 1 d . . . H66 H 0.1105 0.0723 0.1914 0.091 Uiso 1 1 calc R . . N3 N 0.2240(8) 0.2334(6) 0.0504(4) 0.080(2) Uani 1 1 d . . . H67 H 0.2817 0.1719 0.0375 0.096 Uiso 1 1 calc R . . C3 C 0.1146(9) 0.2731(8) 0.2674(5) 0.074(3) Uani 1 1 d . . . H2 H 0.1419 0.2646 0.2198 0.089 Uiso 1 1 calc R . . C4 C 0.1705(9) 0.3229(7) 0.2995(6) 0.069(3) Uani 1 1 d . . . C5 C 0.0627(9) 0.2623(8) -0.1573(5) 0.075(3) Uani 1 1 d . . . H3 H 0.1500 0.2572 -0.1677 0.090 Uiso 1 1 calc R . . H4 H 0.0567 0.1902 -0.1652 0.090 Uiso 1 1 calc R . . C6 C 0.2721(10) 0.4995(8) -0.3173(6) 0.080(3) Uani 1 1 d . . . N4 N 0.3721(8) -0.0453(7) 0.2658(4) 0.084(2) Uani 1 1 d . . . H68 H 0.3185 0.0262 0.2529 0.100 Uiso 1 1 calc R . . C7 C 0.3301(9) 0.4599(8) -0.0863(5) 0.083(3) Uani 1 1 d . . . H5 H 0.3348 0.5347 -0.0818 0.100 Uiso 1 1 calc R . . H6 H 0.2438 0.4621 -0.0727 0.100 Uiso 1 1 calc R . . C8 C 0.2471(10) 0.3308(8) 0.0598(5) 0.075(3) Uani 1 1 d . . . C9 C 0.3708(9) 0.3408(7) 0.0446(5) 0.071(3) Uani 1 1 d . . . C10 C 0.2204(10) -0.1505(8) 0.2752(5) 0.080(3) Uani 1 1 d . . . C11 C 0.0823(8) 0.1503(7) -0.0273(5) 0.074(3) Uani 1 1 d . . . H7 H 0.1723 0.1261 -0.0408 0.089 Uiso 1 1 calc R . . H8 H 0.0544 0.0880 -0.0326 0.089 Uiso 1 1 calc R . . C12 C 0.1224(8) 0.0344(8) 0.0970(5) 0.072(3) Uani 1 1 d . . . C13 C 0.1212(9) -0.0764(8) 0.3236(5) 0.079(3) Uani 1 1 d . . . H9 H 0.1426 -0.1107 0.3735 0.095 Uiso 1 1 calc R . . H10 H 0.1249 0.0050 0.3092 0.095 Uiso 1 1 calc R . . C14 C 0.5195(9) 0.2174(8) 0.3022(5) 0.081(3) Uani 1 1 d . . . H11 H 0.5414 0.2482 0.2507 0.097 Uiso 1 1 calc R . . H12 H 0.5953 0.1869 0.3264 0.097 Uiso 1 1 calc R . . C15 C 0.1637(10) 0.4053(8) -0.3831(5) 0.087(3) Uani 1 1 d . . . H13 H 0.1248 0.3723 -0.4054 0.104 Uiso 1 1 calc R . . C16 C 0.0042(10) 0.3030(9) 0.4867(5) 0.092(3) Uani 1 1 d . . . H14 H 0.0673 0.2435 0.5167 0.138 Uiso 1 1 calc R . . H15 H -0.0745 0.2895 0.5034 0.138 Uiso 1 1 calc R . . H16 H -0.0042 0.3823 0.4899 0.138 Uiso 1 1 calc R . . C17 C 0.0419(10) 0.2934(8) 0.4089(6) 0.084(3) Uani 1 1 d . . . C18 C -0.0185(9) 0.2432(8) 0.3779(5) 0.080(3) Uani 1 1 d . . . H17 H -0.0824 0.2150 0.4050 0.095 Uiso 1 1 calc R . . C19 C 0.4509(9) -0.2388(9) 0.2993(5) 0.086(3) Uani 1 1 d . . . H18 H 0.4613 -0.3209 0.3130 0.103 Uiso 1 1 calc R . . C20 C 0.4631(10) 0.2363(8) 0.0861(6) 0.075(3) Uani 1 1 d . . . C21 C 0.3447(10) -0.1496(9) 0.2802(5) 0.079(3) Uani 1 1 d . . . C22 C -0.0117(9) 0.3684(8) -0.2075(5) 0.081(3) Uani 1 1 d . . . H19 H -0.0981 0.3707 -0.1988 0.098 Uiso 1 1 calc R . . H20 H -0.0099 0.4406 -0.1973 0.098 Uiso 1 1 calc R . . C23 C 0.0571(9) 0.1539(8) 0.0541(5) 0.074(3) Uani 1 1 d . . . C24 C 0.0210(8) 0.2663(8) -0.0808(5) 0.078(3) Uani 1 1 d . . . H21 H -0.0692 0.2844 -0.0726 0.093 Uiso 1 1 calc R . . H22 H 0.0388 0.3316 -0.0713 0.093 Uiso 1 1 calc R . . C25 C 0.3304(9) 0.4076(8) 0.2845(5) 0.083(3) Uani 1 1 d . . . H23 H 0.2700 0.4641 0.3114 0.099 Uiso 1 1 calc R . . H24 H 0.3712 0.4535 0.2439 0.099 Uiso 1 1 calc R . . C26 C 0.3650(9) 0.4525(7) 0.0678(5) 0.084(3) Uani 1 1 d . . . H25 H 0.3009 0.5223 0.0443 0.126 Uiso 1 1 calc R . . H26 H 0.4446 0.4649 0.0538 0.126 Uiso 1 1 calc R . . H27 H 0.3460 0.4399 0.1198 0.126 Uiso 1 1 calc R . . C27 C 0.3688(9) 0.4497(8) -0.1647(5) 0.083(3) Uani 1 1 d . . . H28 H 0.4581 0.4357 -0.1760 0.100 Uiso 1 1 calc R . . H29 H 0.3529 0.3809 -0.1706 0.100 Uiso 1 1 calc R . . C28 C 0.2990(10) 0.5614(8) -0.2168(5) 0.093(3) Uani 1 1 d . . . H30 H 0.2096 0.5761 -0.2050 0.112 Uiso 1 1 calc R . . H31 H 0.3159 0.6300 -0.2114 0.112 Uiso 1 1 calc R . . C29 C 0.3108(10) 0.4936(8) -0.3880(5) 0.080(3) Uani 1 1 d . . . H32 H 0.3751 0.5228 -0.4131 0.096 Uiso 1 1 calc R . . C30 C 0.6807(8) -0.0303(8) 0.2790(5) 0.086(3) Uani 1 1 d . . . H33 H 0.6831 -0.0632 0.3307 0.129 Uiso 1 1 calc R . . H34 H 0.7216 0.0294 0.2632 0.129 Uiso 1 1 calc R . . H35 H 0.7232 -0.0939 0.2540 0.129 Uiso 1 1 calc R . . C31 C 0.5453(10) 0.0954(9) 0.1828(6) 0.084(3) Uani 1 1 d . . . C32 C -0.0813(9) 0.1877(8) 0.0775(5) 0.087(3) Uani 1 1 d . . . H36 H -0.1089 0.1223 0.0790 0.131 Uiso 1 1 calc R . . H37 H -0.1254 0.2589 0.0432 0.131 Uiso 1 1 calc R . . H38 H -0.0980 0.2035 0.1251 0.131 Uiso 1 1 calc R . . C33 C 0.2233(10) -0.2823(7) 0.3011(5) 0.090(3) Uani 1 1 d . . . H39 H 0.2910 -0.3312 0.2736 0.135 Uiso 1 1 calc R . . H40 H 0.1453 -0.2862 0.2938 0.135 Uiso 1 1 calc R . . H41 H 0.2354 -0.3117 0.3520 0.135 Uiso 1 1 calc R . . C34 C 0.1353(10) 0.4043(8) 0.0789(5) 0.076(3) Uani 1 1 d . . . H42 H 0.1193 0.4784 0.0893 0.091 Uiso 1 1 calc R . . C35 C 0.0431(9) 0.3514(8) 0.0811(5) 0.076(3) Uani 1 1 d . . . H43 H -0.0430 0.3849 0.0928 0.092 Uiso 1 1 calc R . . C36 C 0.4892(10) -0.0669(9) 0.2740(5) 0.083(3) Uani 1 1 d . . . C37 C 0.5450(10) 0.0282(8) 0.2617(5) 0.079(3) Uani 1 1 d . . . C38 C 0.6330(9) 0.0830(8) 0.1258(6) 0.078(3) Uani 1 1 d . . . H44 H 0.7141 0.0271 0.1266 0.094 Uiso 1 1 calc R . . C39 C 0.1264(10) 0.4111(8) -0.3138(6) 0.081(3) Uani 1 1 d . . . C40 C -0.1007(10) 0.0294(9) 0.3578(5) 0.090(3) Uani 1 1 d . . . H45 H -0.0626 0.0326 0.3973 0.108 Uiso 1 1 calc R . . H46 H -0.1756 0.0087 0.3789 0.108 Uiso 1 1 calc R . . C41 C 0.1337(9) 0.3329(8) 0.3697(6) 0.077(3) Uani 1 1 d . . . H47 H 0.1730 0.3676 0.3905 0.093 Uiso 1 1 calc R . . C42 C 0.2117(9) -0.1607(9) 0.1445(5) 0.082(3) Uani 1 1 d . . . H48 H 0.2469 -0.2437 0.1489 0.099 Uiso 1 1 calc R . . C43 C 0.5803(10) 0.1691(9) 0.0652(6) 0.087(3) Uani 1 1 d . . . H49 H 0.6197 0.1788 0.0177 0.104 Uiso 1 1 calc R . . C44 C 0.2993(10) 0.4445(9) -0.4986(5) 0.100(3) Uani 1 1 d . . . H50 H 0.3771 0.4605 -0.5122 0.150 Uiso 1 1 calc R . . H51 H 0.2371 0.5054 -0.5287 0.150 Uiso 1 1 calc R . . H52 H 0.3113 0.3665 -0.5054 0.150 Uiso 1 1 calc R . . C45 C 0.1026(9) 0.2455(8) 0.0635(5) 0.071(3) Uani 1 1 d . . . C46 C 0.4259(9) 0.3207(9) 0.3328(5) 0.086(3) Uani 1 1 d . . . H53 H 0.3833 0.2873 0.3782 0.103 Uiso 1 1 calc R . . H54 H 0.4714 0.3643 0.3444 0.103 Uiso 1 1 calc R . . C47 C 0.2575(10) 0.4464(8) -0.4221(6) 0.082(3) Uani 1 1 d . . . C48 C 0.4740(9) 0.1145(8) 0.3105(5) 0.081(3) Uani 1 1 d . . . H55 H 0.3866 0.1479 0.3011 0.097 Uiso 1 1 calc R . . H56 H 0.4774 0.0684 0.3609 0.097 Uiso 1 1 calc R . . C49 C -0.0114(9) -0.0677(8) 0.3226(5) 0.083(3) Uani 1 1 d . . . H57 H -0.0289 -0.0503 0.2725 0.099 Uiso 1 1 calc R . . H58 H -0.0224 -0.1445 0.3484 0.099 Uiso 1 1 calc R . . C50 C -0.3653(10) 0.1191(9) 0.5502(6) 0.103(4) Uani 1 1 d . . . C51 C 0.5456(10) -0.1890(8) 0.2952(5) 0.085(3) Uani 1 1 d . . . H59 H 0.6286 -0.2309 0.3050 0.102 Uiso 1 1 calc R . . C52 C 0.1903(9) -0.1039(8) 0.1975(6) 0.081(3) Uani 1 1 d . . . C53 C 0.4130(10) 0.3553(8) -0.0356(5) 0.089(3) Uani 1 1 d . . . H60 H 0.4956 0.3630 -0.0442 0.107 Uiso 1 1 calc R . . H61 H 0.4220 0.2816 -0.0484 0.107 Uiso 1 1 calc R . . C54 C 0.1717(8) -0.0729(8) 0.0816(5) 0.075(3) Uani 1 1 d . . . H62 H 0.1786 -0.0873 0.0359 0.090 Uiso 1 1 calc R . . C55 C -0.1383(10) 0.1530(8) 0.3061(5) 0.091(3) Uani 1 1 d . . . H63 H -0.1837 0.1520 0.2691 0.109 Uiso 1 1 calc R . . H64 H -0.1947 0.2114 0.3330 0.109 Uiso 1 1 calc R . . Cl3 Cl -0.3125(3) 0.2410(2) 0.49760(16) 0.1155(11) Uani 1 1 d . . . C56 C 0.5428(17) 0.0562(17) -0.0933(7) 0.158(6) Uani 1 1 d D . . H69 H 0.5707 0.1242 -0.1031 0.237 Uiso 1 1 calc R . . H70 H 0.5275 0.0475 -0.1383 0.237 Uiso 1 1 calc R . . H71 H 0.6062 -0.0159 -0.0711 0.237 Uiso 1 1 calc R . . O6 O 0.4298(14) 0.0751(15) -0.0450(14) 0.45(2) Uani 1 1 d D . . H72 H 0.3818 0.0504 -0.0574 0.668 Uiso 1 1 calc R . . 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 0.108(2) 0.0893(18) 0.108(2) -0.0233(15) -0.0129(17) -0.0246(16) Cl2 0.142(3) 0.112(2) 0.137(3) -0.0097(18) -0.055(2) -0.053(2) O1 0.086(5) 0.090(4) 0.070(4) -0.019(3) -0.011(4) -0.034(4) O2 0.066(5) 0.093(4) 0.085(4) -0.023(3) -0.017(4) -0.036(4) O3 0.077(5) 0.069(4) 0.085(4) -0.017(3) -0.016(4) -0.027(3) O4 0.086(5) 0.082(4) 0.086(5) -0.014(3) -0.014(4) -0.034(4) C1 0.078(8) 0.063(5) 0.080(7) -0.024(5) -0.010(6) -0.023(5) N1 0.058(5) 0.077(5) 0.085(6) -0.033(4) 0.003(4) -0.027(4) C2 0.072(7) 0.072(6) 0.074(7) -0.011(5) -0.026(6) -0.021(5) N2 0.080(6) 0.071(5) 0.076(6) -0.027(4) -0.012(4) -0.015(4) N3 0.084(7) 0.069(5) 0.098(6) -0.036(4) -0.011(5) -0.023(4) C3 0.068(7) 0.081(6) 0.079(7) -0.023(5) -0.007(5) -0.028(5) C4 0.065(7) 0.057(5) 0.087(7) -0.018(5) -0.006(6) -0.021(5) C5 0.071(7) 0.080(6) 0.080(7) -0.021(5) -0.013(5) -0.029(5) C6 0.083(8) 0.064(6) 0.092(8) -0.019(5) -0.025(7) -0.015(5) N4 0.074(6) 0.075(5) 0.106(6) -0.017(4) -0.012(5) -0.032(4) C7 0.074(7) 0.081(6) 0.090(8) -0.016(5) 0.001(6) -0.028(5) C8 0.078(8) 0.071(6) 0.091(7) -0.028(5) -0.017(6) -0.032(6) C9 0.068(7) 0.069(6) 0.085(7) -0.022(5) -0.015(6) -0.025(5) C10 0.091(8) 0.072(6) 0.086(7) -0.019(5) -0.014(6) -0.034(6) C11 0.066(7) 0.063(5) 0.092(7) -0.027(5) -0.013(5) -0.012(5) C12 0.060(6) 0.066(6) 0.085(7) -0.013(5) -0.020(5) -0.013(5) C13 0.076(7) 0.085(6) 0.081(7) -0.015(5) -0.012(6) -0.034(6) C14 0.078(7) 0.080(6) 0.092(7) -0.021(5) -0.012(6) -0.031(6) C15 0.113(10) 0.089(7) 0.063(7) -0.018(5) -0.003(6) -0.041(7) C16 0.105(9) 0.104(7) 0.072(7) -0.024(5) 0.005(6) -0.044(7) C17 0.077(8) 0.080(6) 0.092(8) -0.021(5) -0.022(6) -0.016(6) C18 0.080(8) 0.078(6) 0.091(8) -0.014(5) -0.026(6) -0.035(5) C19 0.068(7) 0.092(7) 0.107(8) -0.031(6) -0.023(6) -0.027(6) C20 0.071(7) 0.071(6) 0.093(8) -0.029(6) -0.013(6) -0.025(5) C21 0.065(7) 0.087(7) 0.097(7) -0.022(5) -0.026(6) -0.031(6) C22 0.078(7) 0.096(7) 0.075(7) -0.013(5) -0.015(6) -0.035(6) C23 0.053(6) 0.091(7) 0.076(7) -0.022(5) -0.004(5) -0.022(5) C24 0.065(7) 0.080(6) 0.084(7) -0.016(5) -0.008(5) -0.021(5) C25 0.084(8) 0.079(6) 0.093(7) -0.025(5) -0.008(6) -0.033(6) C26 0.092(8) 0.075(6) 0.095(7) -0.024(5) -0.023(6) -0.029(6) C27 0.068(7) 0.090(7) 0.100(8) -0.026(6) -0.002(6) -0.036(6) C28 0.120(10) 0.074(6) 0.090(8) -0.016(6) -0.021(7) -0.035(6) C29 0.083(8) 0.082(7) 0.073(7) -0.015(5) -0.012(6) -0.026(6) C30 0.064(7) 0.090(7) 0.113(8) -0.033(6) -0.017(6) -0.024(5) C31 0.062(7) 0.085(7) 0.110(9) -0.039(6) -0.011(6) -0.017(6) C32 0.077(8) 0.086(7) 0.104(8) -0.037(6) 0.001(6) -0.028(6) C33 0.116(9) 0.056(5) 0.113(8) -0.017(5) -0.032(7) -0.039(5) C34 0.082(8) 0.061(5) 0.087(7) -0.028(5) -0.011(6) -0.018(5) C35 0.058(7) 0.084(7) 0.081(7) -0.023(5) -0.007(5) -0.014(5) C36 0.057(7) 0.099(8) 0.101(8) -0.021(6) -0.016(6) -0.033(6) C37 0.080(8) 0.078(6) 0.089(7) -0.020(5) -0.012(6) -0.036(6) C38 0.051(6) 0.089(7) 0.098(8) -0.039(6) 0.005(6) -0.020(5) C39 0.074(8) 0.067(6) 0.098(8) -0.019(6) -0.011(6) -0.019(5) C40 0.084(8) 0.125(9) 0.084(7) -0.004(6) -0.024(6) -0.067(7) C41 0.067(7) 0.077(6) 0.090(8) -0.024(5) -0.004(6) -0.027(5) C42 0.088(8) 0.076(6) 0.093(8) -0.018(6) -0.032(6) -0.030(5) C43 0.081(8) 0.094(7) 0.086(8) -0.010(6) -0.019(6) -0.034(6) C44 0.110(9) 0.098(7) 0.088(8) -0.042(6) 0.000(7) -0.023(7) C45 0.047(6) 0.080(6) 0.093(7) -0.036(5) -0.008(5) -0.016(5) C46 0.068(7) 0.091(7) 0.109(8) -0.025(6) -0.015(6) -0.035(6) C47 0.084(8) 0.070(6) 0.083(8) -0.018(5) -0.012(6) -0.013(5) C48 0.083(8) 0.076(6) 0.087(7) -0.037(5) 0.001(6) -0.024(5) C49 0.071(7) 0.083(7) 0.095(7) -0.023(6) 0.005(6) -0.034(6) C50 0.076(8) 0.087(7) 0.152(10) -0.035(7) -0.029(7) -0.020(6) C51 0.075(8) 0.075(6) 0.099(8) -0.022(5) -0.025(6) -0.009(5) C52 0.085(8) 0.072(6) 0.097(8) -0.022(6) -0.018(6) -0.032(5) C53 0.092(8) 0.081(6) 0.094(8) -0.021(6) -0.007(6) -0.029(6) C54 0.056(6) 0.083(6) 0.083(7) -0.025(5) -0.005(5) -0.016(5) C55 0.101(9) 0.086(7) 0.100(8) -0.025(6) -0.016(6) -0.044(6) Cl3 0.115(3) 0.0981(19) 0.130(3) -0.0206(17) 0.000(2) -0.0444(18) C56 0.138(14) 0.242(19) 0.149(12) -0.058(12) 0.001(12) -0.125(15) O6 0.177(15) 0.238(18) 1.05(7) -0.35(3) -0.19(2) 0.007(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 Cl1 C50 1.759(10) . ? Cl2 C50 1.743(11) . ? O1 C6 1.403(11) . ? O1 C28 1.431(10) . ? O2 C2 1.359(10) . ? O2 C55 1.443(10) . ? O3 C4 1.385(10) . ? O3 C25 1.429(10) . ? O4 C39 1.372(11) . ? O4 C22 1.436(10) . ? C1 C6 1.353(13) . ? C1 C39 1.386(12) . ? C1 H1 0.9500 . ? N1 C20 1.391(11) . ? N1 C31 1.397(11) . ? N1 H65 0.8800 . ? C2 C3 1.387(12) . ? C2 C18 1.412(12) . ? N2 C12 1.373(10) . ? N2 C52 1.392(11) . ? N2 H66 0.8800 . ? N3 C45 1.360(11) . ? N3 C8 1.413(10) . ? N3 H67 0.8800 . ? C3 C4 1.389(12) . ? C3 H2 0.9500 . ? C4 C41 1.387(12) . ? C5 C22 1.488(11) . ? C5 C24 1.495(11) . ? C5 H3 0.9900 . ? C5 H4 0.9900 . ? C6 C29 1.386(12) . ? N4 C36 1.338(11) . ? N4 C21 1.398(11) . ? N4 H68 0.8800 . ? C7 C53 1.528(12) . ? C7 C27 1.545(12) . ? C7 H5 0.9900 . ? C7 H6 0.9900 . ? C8 C34 1.351(12) . ? C8 C9 1.473(12) . ? C9 C20 1.494(12) . ? C9 C53 1.532(12) . ? C9 C26 1.569(11) . ? C10 C21 1.492(13) . ? C10 C52 1.528(13) . ? C10 C13 1.548(12) . ? C10 C33 1.569(11) . ? C11 C24 1.537(11) . ? C11 C23 1.579(12) . ? C11 H7 0.9900 . ? C11 H8 0.9900 . ? C12 C54 1.350(11) . ? C12 C23 1.485(12) . ? C13 C49 1.531(12) . ? C13 H9 0.9900 . ? C13 H10 0.9900 . ? C14 C48 1.528(12) . ? C14 C46 1.543(12) . ? C14 H11 0.9900 . ? C14 H12 0.9900 . ? C15 C39 1.359(12) . ? C15 C47 1.388(13) . ? C15 H13 0.9500 . ? C16 C17 1.532(12) . ? C16 H14 0.9800 . ? C16 H15 0.9800 . ? C16 H16 0.9800 . ? C17 C41 1.360(12) . ? C17 C18 1.418(12) . ? C18 H17 0.9500 . ? C19 C21 1.362(13) . ? C19 C51 1.448(13) . ? C19 H18 0.9500 . ? C20 C43 1.375(13) . ? C22 H19 0.9900 . ? C22 H20 0.9900 . ? C23 C45 1.505(12) . ? C23 C32 1.532(12) . ? C24 H21 0.9900 . ? C24 H22 0.9900 . ? C25 C46 1.504(12) . ? C25 H23 0.9900 . ? C25 H24 0.9900 . ? C26 H25 0.9800 . ? C26 H26 0.9800 . ? C26 H27 0.9800 . ? C27 C28 1.524(12) . ? C27 H28 0.9900 . ? C27 H29 0.9900 . ? C28 H30 0.9900 . ? C28 H31 0.9900 . ? C29 C47 1.370(12) . ? C29 H32 0.9500 . ? C30 C37 1.551(12) . ? C30 H33 0.9800 . ? C30 H34 0.9800 . ? C30 H35 0.9800 . ? C31 C38 1.365(12) . ? C31 C37 1.533(13) . ? C32 H36 0.9800 . ? C32 H37 0.9800 . ? C32 H38 0.9800 . ? C33 H39 0.9800 . ? C33 H40 0.9800 . ? C33 H41 0.9800 . ? C34 C35 1.458(12) . ? C34 H42 0.9500 . ? C35 C45 1.360(11) . ? C35 H43 0.9500 . ? C36 C51 1.391(12) . ? C36 C37 1.505(12) . ? C37 C48 1.549(12) . ? C38 C43 1.418(12) . ? C38 H44 0.9500 . ? C40 C49 1.520(12) . ? C40 C55 1.540(13) . ? C40 H45 0.9900 . ? C40 H46 0.9900 . ? C41 H47 0.9500 . ? C42 C52 1.359(12) . ? C42 C54 1.417(12) . ? C42 H48 0.9500 . ? C43 H49 0.9500 . ? C44 C47 1.489(12) . ? C44 H50 0.9800 . ? C44 H51 0.9800 . ? C44 H52 0.9800 . ? C46 H53 0.9900 . ? C46 H54 0.9900 . ? C48 H55 0.9900 . ? C48 H56 0.9900 . ? C49 H57 0.9900 . ? C49 H58 0.9900 . ? C50 Cl3 1.821(11) . ? C51 H59 0.9500 . ? C53 H60 0.9900 . ? C53 H61 0.9900 . ? C54 H62 0.9500 . ? C55 H63 0.9900 . ? C55 H64 0.9900 . ? C56 O6 1.456(10) . ? C56 H69 0.9800 . ? C56 H70 0.9800 . ? C56 H71 0.9800 . ? O6 H72 0.8400 . ? 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 C6 O1 C28 118.5(8) . . ? C2 O2 C55 120.6(8) . . ? C4 O3 C25 118.7(7) . . ? C39 O4 C22 120.2(8) . . ? C6 C1 C39 118.1(10) . . ? C6 C1 H1 121.0 . . ? C39 C1 H1 121.0 . . ? C20 N1 C31 109.1(8) . . ? C20 N1 H65 125.4 . . ? C31 N1 H65 125.4 . . ? O2 C2 C3 116.4(9) . . ? O2 C2 C18 123.0(9) . . ? C3 C2 C18 120.6(10) . . ? C12 N2 C52 110.1(8) . . ? C12 N2 H66 125.0 . . ? C52 N2 H66 125.0 . . ? C45 N3 C8 112.4(8) . . ? C45 N3 H67 123.8 . . ? C8 N3 H67 123.8 . . ? C2 C3 C4 118.9(10) . . ? C2 C3 H2 120.5 . . ? C4 C3 H2 120.5 . . ? O3 C4 C41 124.8(9) . . ? O3 C4 C3 114.1(9) . . ? C41 C4 C3 121.1(9) . . ? C22 C5 C24 112.2(8) . . ? C22 C5 H3 109.2 . . ? C24 C5 H3 109.2 . . ? C22 C5 H4 109.2 . . ? C24 C5 H4 109.2 . . ? H3 C5 H4 107.9 . . ? C1 C6 C29 121.4(11) . . ? C1 C6 O1 123.7(10) . . ? C29 C6 O1 114.9(10) . . ? C36 N4 C21 112.2(9) . . ? C36 N4 H68 123.9 . . ? C21 N4 H68 123.9 . . ? C53 C7 C27 111.1(8) . . ? C53 C7 H5 109.4 . . ? C27 C7 H5 109.4 . . ? C53 C7 H6 109.4 . . ? C27 C7 H6 109.4 . . ? H5 C7 H6 108.0 . . ? C34 C8 N3 104.7(9) . . ? C34 C8 C9 132.9(9) . . ? N3 C8 C9 122.2(9) . . ? C8 C9 C20 112.3(8) . . ? C8 C9 C53 110.1(8) . . ? C20 C9 C53 109.5(8) . . ? C8 C9 C26 108.5(8) . . ? C20 C9 C26 107.0(8) . . ? C53 C9 C26 109.4(7) . . ? C21 C10 C52 110.3(8) . . ? C21 C10 C13 110.7(8) . . ? C52 C10 C13 110.7(8) . . ? C21 C10 C33 107.9(9) . . ? C52 C10 C33 108.1(7) . . ? C13 C10 C33 109.0(8) . . ? C24 C11 C23 116.2(7) . . ? C24 C11 H7 108.2 . . ? C23 C11 H7 108.2 . . ? C24 C11 H8 108.2 . . ? C23 C11 H8 108.2 . . ? H7 C11 H8 107.4 . . ? C54 C12 N2 106.6(8) . . ? C54 C12 C23 132.2(9) . . ? N2 C12 C23 121.1(8) . . ? C49 C13 C10 116.3(8) . . ? C49 C13 H9 108.2 . . ? C10 C13 H9 108.2 . . ? C49 C13 H10 108.2 . . ? C10 C13 H10 108.2 . . ? H9 C13 H10 107.4 . . ? C48 C14 C46 114.4(8) . . ? C48 C14 H11 108.7 . . ? C46 C14 H11 108.7 . . ? C48 C14 H12 108.7 . . ? C46 C14 H12 108.7 . . ? H11 C14 H12 107.6 . . ? C39 C15 C47 121.6(11) . . ? C39 C15 H13 119.2 . . ? C47 C15 H13 119.2 . . ? C17 C16 H14 109.5 . . ? C17 C16 H15 109.5 . . ? H14 C16 H15 109.5 . . ? C17 C16 H16 109.5 . . ? H14 C16 H16 109.5 . . ? H15 C16 H16 109.5 . . ? C41 C17 C18 120.2(10) . . ? C41 C17 C16 119.8(10) . . ? C18 C17 C16 120.0(10) . . ? C2 C18 C17 118.5(10) . . ? C2 C18 H17 120.7 . . ? C17 C18 H17 120.7 . . ? C21 C19 C51 109.4(9) . . ? C21 C19 H18 125.3 . . ? C51 C19 H18 125.3 . . ? C43 C20 N1 106.5(9) . . ? C43 C20 C9 130.9(10) . . ? N1 C20 C9 122.6(9) . . ? C19 C21 N4 105.1(9) . . ? C19 C21 C10 131.8(10) . . ? N4 C21 C10 123.0(9) . . ? O4 C22 C5 113.3(8) . . ? O4 C22 H19 108.9 . . ? C5 C22 H19 108.9 . . ? O4 C22 H20 108.9 . . ? C5 C22 H20 108.9 . . ? H19 C22 H20 107.7 . . ? C12 C23 C45 110.9(8) . . ? C12 C23 C32 109.8(8) . . ? C45 C23 C32 109.1(8) . . ? C12 C23 C11 108.3(8) . . ? C45 C23 C11 109.0(7) . . ? C32 C23 C11 109.7(8) . . ? C5 C24 C11 113.6(7) . . ? C5 C24 H21 108.8 . . ? C11 C24 H21 108.8 . . ? C5 C24 H22 108.8 . . ? C11 C24 H22 108.8 . . ? H21 C24 H22 107.7 . . ? O3 C25 C46 115.6(7) . . ? O3 C25 H23 108.4 . . ? C46 C25 H23 108.4 . . ? O3 C25 H24 108.4 . . ? C46 C25 H24 108.4 . . ? H23 C25 H24 107.4 . . ? C9 C26 H25 109.5 . . ? C9 C26 H26 109.5 . . ? H25 C26 H26 109.5 . . ? C9 C26 H27 109.5 . . ? H25 C26 H27 109.5 . . ? H26 C26 H27 109.5 . . ? C28 C27 C7 111.6(8) . . ? C28 C27 H28 109.3 . . ? C7 C27 H28 109.3 . . ? C28 C27 H29 109.3 . . ? C7 C27 H29 109.3 . . ? H28 C27 H29 108.0 . . ? O1 C28 C27 111.9(8) . . ? O1 C28 H30 109.2 . . ? C27 C28 H30 109.2 . . ? O1 C28 H31 109.2 . . ? C27 C28 H31 109.2 . . ? H30 C28 H31 107.9 . . ? C47 C29 C6 120.9(11) . . ? C47 C29 H32 119.5 . . ? C6 C29 H32 119.5 . . ? C37 C30 H33 109.5 . . ? C37 C30 H34 109.5 . . ? H33 C30 H34 109.5 . . ? C37 C30 H35 109.5 . . ? H33 C30 H35 109.5 . . ? H34 C30 H35 109.5 . . ? C38 C31 N1 108.1(9) . . ? C38 C31 C37 132.2(10) . . ? N1 C31 C37 119.7(10) . . ? C23 C32 H36 109.5 . . ? C23 C32 H37 109.5 . . ? H36 C32 H37 109.5 . . ? C23 C32 H38 109.5 . . ? H36 C32 H38 109.5 . . ? H37 C32 H38 109.5 . . ? C10 C33 H39 109.5 . . ? C10 C33 H40 109.5 . . ? H39 C33 H40 109.5 . . ? C10 C33 H41 109.5 . . ? H39 C33 H41 109.5 . . ? H40 C33 H41 109.5 . . ? C8 C34 C35 108.8(8) . . ? C8 C34 H42 125.6 . . ? C35 C34 H42 125.6 . . ? C45 C35 C34 107.6(8) . . ? C45 C35 H43 126.2 . . ? C34 C35 H43 126.2 . . ? N4 C36 C51 107.9(9) . . ? N4 C36 C37 124.0(9) . . ? C51 C36 C37 128.1(10) . . ? C36 C37 C31 109.8(8) . . ? C36 C37 C48 110.7(8) . . ? C31 C37 C48 110.6(8) . . ? C36 C37 C30 109.2(8) . . ? C31 C37 C30 107.5(8) . . ? C48 C37 C30 108.9(8) . . ? C31 C38 C43 107.1(9) . . ? C31 C38 H44 126.5 . . ? C43 C38 H44 126.5 . . ? C15 C39 O4 116.2(10) . . ? C15 C39 C1 120.8(10) . . ? O4 C39 C1 123.1(10) . . ? C49 C40 C55 113.8(8) . . ? C49 C40 H45 108.8 . . ? C55 C40 H45 108.8 . . ? C49 C40 H46 108.8 . . ? C55 C40 H46 108.8 . . ? H45 C40 H46 107.7 . . ? C17 C41 C4 120.5(10) . . ? C17 C41 H47 119.7 . . ? C4 C41 H47 119.7 . . ? C52 C42 C54 107.3(9) . . ? C52 C42 H48 126.3 . . ? C54 C42 H48 126.3 . . ? C20 C43 C38 109.2(9) . . ? C20 C43 H49 125.4 . . ? C38 C43 H49 125.4 . . ? C47 C44 H50 109.5 . . ? C47 C44 H51 109.5 . . ? H50 C44 H51 109.5 . . ? C47 C44 H52 109.5 . . ? H50 C44 H52 109.5 . . ? H51 C44 H52 109.5 . . ? C35 C45 N3 106.4(8) . . ? C35 C45 C23 132.2(9) . . ? N3 C45 C23 121.2(8) . . ? C25 C46 C14 115.3(8) . . ? C25 C46 H53 108.4 . . ? C14 C46 H53 108.4 . . ? C25 C46 H54 108.4 . . ? C14 C46 H54 108.4 . . ? H53 C46 H54 107.5 . . ? C29 C47 C15 117.2(11) . . ? C29 C47 C44 119.3(10) . . ? C15 C47 C44 123.5(11) . . ? C14 C48 C37 116.2(8) . . ? C14 C48 H55 108.2 . . ? C37 C48 H55 108.2 . . ? C14 C48 H56 108.2 . . ? C37 C48 H56 108.2 . . ? H55 C48 H56 107.4 . . ? C40 C49 C13 110.4(8) . . ? C40 C49 H57 109.6 . . ? C13 C49 H57 109.6 . . ? C40 C49 H58 109.6 . . ? C13 C49 H58 109.6 . . ? H57 C49 H58 108.1 . . ? Cl2 C50 Cl1 110.8(6) . . ? Cl2 C50 Cl3 107.0(6) . . ? Cl1 C50 Cl3 109.1(6) . . ? C36 C51 C19 105.4(9) . . ? C36 C51 H59 127.3 . . ? C19 C51 H59 127.3 . . ? C42 C52 N2 106.8(9) . . ? C42 C52 C10 131.3(9) . . ? N2 C52 C10 121.9(9) . . ? C7 C53 C9 116.6(8) . . ? C7 C53 H60 108.1 . . ? C9 C53 H60 108.1 . . ? C7 C53 H61 108.1 . . ? C9 C53 H61 108.1 . . ? H60 C53 H61 107.3 . . ? C12 C54 C42 109.2(9) . . ? C12 C54 H62 125.4 . . ? C42 C54 H62 125.4 . . ? O2 C55 C40 113.1(8) . . ? O2 C55 H63 109.0 . . ? C40 C55 H63 109.0 . . ? O2 C55 H64 109.0 . . ? C40 C55 H64 109.0 . . ? H63 C55 H64 107.8 . . ? O6 C56 H69 109.5 . . ? O6 C56 H70 109.5 . . ? H69 C56 H70 109.5 . . ? O6 C56 H71 109.5 . . ? H69 C56 H71 109.5 . . ? H70 C56 H71 109.5 . . ? C56 O6 H72 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 C55 O2 C2 C3 -178.0(8) . . . . ? C55 O2 C2 C18 3.5(12) . . . . ? O2 C2 C3 C4 178.4(7) . . . . ? C18 C2 C3 C4 -3.1(13) . . . . ? C25 O3 C4 C41 -0.7(12) . . . . ? C25 O3 C4 C3 -179.0(7) . . . . ? C2 C3 C4 O3 -179.9(7) . . . . ? C2 C3 C4 C41 1.8(13) . . . . ? C39 C1 C6 C29 -1.3(14) . . . . ? C39 C1 C6 O1 178.2(8) . . . . ? C28 O1 C6 C1 0.5(13) . . . . ? C28 O1 C6 C29 -180.0(8) . . . . ? C45 N3 C8 C34 -0.3(11) . . . . ? C45 N3 C8 C9 -176.4(8) . . . . ? C34 C8 C9 C20 128.5(12) . . . . ? N3 C8 C9 C20 -56.6(12) . . . . ? C34 C8 C9 C53 -109.1(12) . . . . ? N3 C8 C9 C53 65.7(11) . . . . ? C34 C8 C9 C26 10.5(15) . . . . ? N3 C8 C9 C26 -174.6(8) . . . . ? C52 N2 C12 C54 -0.9(10) . . . . ? C52 N2 C12 C23 175.3(8) . . . . ? C21 C10 C13 C49 178.9(8) . . . . ? C52 C10 C13 C49 56.2(11) . . . . ? C33 C10 C13 C49 -62.5(11) . . . . ? O2 C2 C18 C17 -179.2(8) . . . . ? C3 C2 C18 C17 2.4(13) . . . . ? C41 C17 C18 C2 -0.3(13) . . . . ? C16 C17 C18 C2 179.9(8) . . . . ? C31 N1 C20 C43 -0.1(10) . . . . ? C31 N1 C20 C9 -178.6(8) . . . . ? C8 C9 C20 C43 134.3(11) . . . . ? C53 C9 C20 C43 11.6(14) . . . . ? C26 C9 C20 C43 -106.9(12) . . . . ? C8 C9 C20 N1 -47.6(12) . . . . ? C53 C9 C20 N1 -170.3(8) . . . . ? C26 C9 C20 N1 71.3(11) . . . . ? C51 C19 C21 N4 -1.1(11) . . . . ? C51 C19 C21 C10 -179.9(10) . . . . ? C36 N4 C21 C19 1.0(12) . . . . ? C36 N4 C21 C10 179.9(9) . . . . ? C52 C10 C21 C19 -114.8(12) . . . . ? C13 C10 C21 C19 122.3(12) . . . . ? C33 C10 C21 C19 3.1(16) . . . . ? C52 C10 C21 N4 66.6(12) . . . . ? C13 C10 C21 N4 -56.3(12) . . . . ? C33 C10 C21 N4 -175.5(8) . . . . ? C39 O4 C22 C5 -83.0(10) . . . . ? C24 C5 C22 O4 176.6(7) . . . . ? C54 C12 C23 C45 -135.8(10) . . . . ? N2 C12 C23 C45 49.1(12) . . . . ? C54 C12 C23 C32 103.6(12) . . . . ? N2 C12 C23 C32 -71.5(11) . . . . ? C54 C12 C23 C11 -16.2(14) . . . . ? N2 C12 C23 C11 168.7(8) . . . . ? C24 C11 C23 C12 179.4(8) . . . . ? C24 C11 C23 C45 -59.8(10) . . . . ? C24 C11 C23 C32 59.6(10) . . . . ? C22 C5 C24 C11 171.3(8) . . . . ? C23 C11 C24 C5 171.6(8) . . . . ? C4 O3 C25 C46 79.1(10) . . . . ? C53 C7 C27 C28 -171.9(8) . . . . ? C6 O1 C28 C27 86.3(10) . . . . ? C7 C27 C28 O1 -179.2(8) . . . . ? C1 C6 C29 C47 0.6(14) . . . . ? O1 C6 C29 C47 -178.9(8) . . . . ? C20 N1 C31 C38 1.6(10) . . . . ? C20 N1 C31 C37 -179.5(8) . . . . ? N3 C8 C34 C35 -0.1(10) . . . . ? C9 C8 C34 C35 175.4(9) . . . . ? C8 C34 C35 C45 0.5(10) . . . . ? C21 N4 C36 C51 -0.4(12) . . . . ? C21 N4 C36 C37 179.6(9) . . . . ? N4 C36 C37 C31 -64.2(13) . . . . ? C51 C36 C37 C31 115.8(12) . . . . ? N4 C36 C37 C48 58.2(13) . . . . ? C51 C36 C37 C48 -121.8(12) . . . . ? N4 C36 C37 C30 178.1(9) . . . . ? C51 C36 C37 C30 -1.9(15) . . . . ? C38 C31 C37 C36 -95.7(13) . . . . ? N1 C31 C37 C36 85.8(11) . . . . ? C38 C31 C37 C48 141.8(10) . . . . ? N1 C31 C37 C48 -36.7(12) . . . . ? C38 C31 C37 C30 23.0(14) . . . . ? N1 C31 C37 C30 -155.5(8) . . . . ? N1 C31 C38 C43 -2.5(10) . . . . ? C37 C31 C38 C43 178.9(10) . . . . ? C47 C15 C39 O4 178.6(8) . . . . ? C47 C15 C39 C1 -0.4(15) . . . . ? C22 O4 C39 C15 177.6(8) . . . . ? C22 O4 C39 C1 -3.4(12) . . . . ? C6 C1 C39 C15 1.2(14) . . . . ? C6 C1 C39 O4 -177.8(8) . . . . ? C18 C17 C41 C4 -1.0(14) . . . . ? C16 C17 C41 C4 178.8(8) . . . . ? O3 C4 C41 C17 -177.9(8) . . . . ? C3 C4 C41 C17 0.3(14) . . . . ? N1 C20 C43 C38 -1.4(11) . . . . ? C9 C20 C43 C38 176.9(9) . . . . ? C31 C38 C43 C20 2.5(11) . . . . ? C34 C35 C45 N3 -0.6(10) . . . . ? C34 C35 C45 C23 -177.4(10) . . . . ? C8 N3 C45 C35 0.6(11) . . . . ? C8 N3 C45 C23 177.8(8) . . . . ? C12 C23 C45 C35 -128.3(11) . . . . ? C32 C23 C45 C35 -7.3(14) . . . . ? C11 C23 C45 C35 112.5(11) . . . . ? C12 C23 C45 N3 55.3(12) . . . . ? C32 C23 C45 N3 176.3(8) . . . . ? C11 C23 C45 N3 -63.9(11) . . . . ? O3 C25 C46 C14 51.6(11) . . . . ? C48 C14 C46 C25 -82.3(11) . . . . ? C6 C29 C47 C15 0.1(14) . . . . ? C6 C29 C47 C44 178.4(9) . . . . ? C39 C15 C47 C29 -0.3(14) . . . . ? C39 C15 C47 C44 -178.4(9) . . . . ? C46 C14 C48 C37 162.0(8) . . . . ? C36 C37 C48 C14 -178.7(9) . . . . ? C31 C37 C48 C14 -56.7(11) . . . . ? C30 C37 C48 C14 61.2(11) . . . . ? C55 C40 C49 C13 87.3(10) . . . . ? C10 C13 C49 C40 -166.6(8) . . . . ? N4 C36 C51 C19 -0.3(11) . . . . ? C37 C36 C51 C19 179.7(10) . . . . ? C21 C19 C51 C36 0.9(12) . . . . ? C54 C42 C52 N2 1.8(11) . . . . ? C54 C42 C52 C10 -176.1(10) . . . . ? C12 N2 C52 C42 -0.6(11) . . . . ? C12 N2 C52 C10 177.5(9) . . . . ? C21 C10 C52 C42 89.6(13) . . . . ? C13 C10 C52 C42 -147.4(11) . . . . ? C33 C10 C52 C42 -28.1(16) . . . . ? C21 C10 C52 N2 -88.0(11) . . . . ? C13 C10 C52 N2 34.9(12) . . . . ? C33 C10 C52 N2 154.2(9) . . . . ? C27 C7 C53 C9 -168.5(7) . . . . ? C8 C9 C53 C7 57.1(11) . . . . ? C20 C9 C53 C7 -179.0(8) . . . . ? C26 C9 C53 C7 -62.0(11) . . . . ? N2 C12 C54 C42 2.0(10) . . . . ? C23 C12 C54 C42 -173.6(10) . . . . ? C52 C42 C54 C12 -2.5(11) . . . . ? C2 O2 C55 C40 -80.0(10) . . . . ? C49 C40 C55 O2 -57.4(11) . . . . ? 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 H65 O3 0.88 2.37 3.129(9) 144.9 . N2 H66 O2 0.88 2.45 3.254(9) 153.0 . N3 H67 O6 0.88 2.36 3.176(18) 154.0 . _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 60.00 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.333 _refine_diff_density_min -0.352 _refine_diff_density_rms 0.071