# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'RSC Advances' _journal_coden_Cambridge 1500 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Samar Das' _publ_contact_author_email skdsc@uohyd.ernet.in _publ_section_title ; Ammonium-Crown Ether Based Host-Guest Systems: N-H***O Hydrogen Bond Directed Guest Inclusion Featuring N-H Donor Functionalities in Angular Geometry ; _publ_author_name S.Das # Attachment '- Structures(3).cif' data_3AP-12C4 _database_code_depnum_ccdc_archive 'CCDC 846227' #TrackingRef '- Structures(3).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C8 H16 O4), C5 H8 N2, 2(Cl O4)' _chemical_formula_sum 'C21 H40 Cl2 N2 O16' _chemical_formula_weight 647.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.3389(4) _cell_length_b 14.6212(7) _cell_length_c 12.1621(6) _cell_angle_alpha 90.00 _cell_angle_beta 104.483(1) _cell_angle_gamma 90.00 _cell_volume 1435.74(12) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9843 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 25.97 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.498 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 684 _exptl_absorpt_coefficient_mu 0.304 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.9144 _exptl_absorpt_correction_T_max 0.9417 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD 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 10739 _diffrn_reflns_av_R_equivalents 0.0222 _diffrn_reflns_av_sigmaI/netI 0.0313 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5034 _reflns_number_gt 4902 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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. ; _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^)+(0.0672P)^2^+2.1477P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.03(7) _refine_ls_number_reflns 5034 _refine_ls_number_parameters 386 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0512 _refine_ls_R_factor_gt 0.0500 _refine_ls_wR_factor_ref 0.1291 _refine_ls_wR_factor_gt 0.1279 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 C2 C 0.7218(4) 0.1104(2) 0.0987(3) 0.0151(7) Uani 1 1 d . . . C1 C 0.7518(4) 0.1109(3) 0.2148(3) 0.0188(7) Uani 1 1 d . . . H1 H 0.8153 0.0639 0.2593 0.023 Uiso 1 1 calc R . . C5 C 0.5984(4) 0.2478(3) 0.2038(3) 0.0209(8) Uani 1 1 d . . . H5 H 0.5587 0.2961 0.2420 0.025 Uiso 1 1 calc R . . C4 C 0.5637(4) 0.2471(3) 0.0879(3) 0.0198(7) Uani 1 1 d . . . H4 H 0.4980 0.2942 0.0452 0.024 Uiso 1 1 calc R . . C3 C 0.6253(4) 0.1769(2) 0.0329(3) 0.0170(7) Uani 1 1 d . . . H3 H 0.6017 0.1747 -0.0476 0.020 Uiso 1 1 calc R . . C6 C 0.2034(5) -0.0510(3) 0.1877(4) 0.0303(9) Uani 1 1 d . . . H6A H 0.1365 -0.1002 0.2102 0.036 Uiso 1 1 calc R . . H6B H 0.3154 -0.0531 0.2400 0.036 Uiso 1 1 calc R . . C7 C 0.2170(6) -0.0684(3) 0.0667(5) 0.0425(12) Uani 1 1 d . . . H7A H 0.2879 -0.0213 0.0441 0.051 Uiso 1 1 calc R . . H7B H 0.2670 -0.1291 0.0615 0.051 Uiso 1 1 calc R . . C8 C 0.0556(5) -0.0502(3) -0.1212(4) 0.0289(9) Uani 1 1 d . . . H8A H -0.0520 -0.0704 -0.1702 0.035 Uiso 1 1 calc R . . H8B H 0.1437 -0.0877 -0.1401 0.035 Uiso 1 1 calc R . . C9 C 0.0836(6) 0.0505(4) -0.1456(4) 0.0383(11) Uani 1 1 d . . . H9A H 0.1908 0.0720 -0.0972 0.046 Uiso 1 1 calc R . . H9B H 0.0849 0.0587 -0.2262 0.046 Uiso 1 1 calc R . . C10 C -0.0225(5) 0.1967(3) -0.1187(3) 0.0289(9) Uani 1 1 d . . . H10A H -0.1306 0.2277 -0.1280 0.035 Uiso 1 1 calc R . . H10B H 0.0230 0.2146 -0.1833 0.035 Uiso 1 1 calc R . . C11 C 0.0946(6) 0.2284(3) -0.0089(4) 0.0399(11) Uani 1 1 d . . . H11A H 0.2043 0.1991 0.0011 0.048 Uiso 1 1 calc R . . H11B H 0.1093 0.2956 -0.0099 0.048 Uiso 1 1 calc R . . C12 C 0.1369(5) 0.1977(3) 0.1889(4) 0.0314(9) Uani 1 1 d . . . H12A H 0.0755 0.2013 0.2487 0.038 Uiso 1 1 calc R . . H12B H 0.2130 0.2508 0.1985 0.038 Uiso 1 1 calc R . . C13 C 0.2398(6) 0.1081(4) 0.2042(4) 0.0473(13) Uani 1 1 d . . . H13A H 0.2987 0.1020 0.1432 0.057 Uiso 1 1 calc R . . H13B H 0.3226 0.1079 0.2784 0.057 Uiso 1 1 calc R . . C14 C 0.9445(6) 0.3335(3) 0.4715(4) 0.0336(10) Uani 1 1 d . . . H14A H 0.9249 0.3697 0.4007 0.040 Uiso 1 1 calc R . . H14B H 1.0436 0.3588 0.5256 0.040 Uiso 1 1 calc R . . C15 C 0.7988(6) 0.3429(3) 0.5209(3) 0.0321(9) Uani 1 1 d . . . H15A H 0.8192 0.3097 0.5941 0.039 Uiso 1 1 calc R . . H15B H 0.7797 0.4082 0.5351 0.039 Uiso 1 1 calc R . . C16 C 0.5237(6) 0.2879(3) 0.4908(4) 0.0323(10) Uani 1 1 d . . . H16A H 0.4186 0.2932 0.4314 0.039 Uiso 1 1 calc R . . H16B H 0.5221 0.3337 0.5505 0.039 Uiso 1 1 calc R . . C17 C 0.5377(5) 0.1938(3) 0.5414(3) 0.0270(9) Uani 1 1 d . . . H17A H 0.6388 0.1889 0.6044 0.032 Uiso 1 1 calc R . . H17B H 0.4403 0.1804 0.5715 0.032 Uiso 1 1 calc R . . C18 C 0.5964(5) 0.0410(3) 0.4920(3) 0.0283(9) Uani 1 1 d . . . H18A H 0.5675 -0.0015 0.4267 0.034 Uiso 1 1 calc R . . H18B H 0.5342 0.0217 0.5475 0.034 Uiso 1 1 calc R . . C19 C 0.7770(5) 0.0335(3) 0.5459(3) 0.0284(9) Uani 1 1 d . . . H19A H 0.8083 0.0747 0.6125 0.034 Uiso 1 1 calc R . . H19B H 0.8056 -0.0300 0.5717 0.034 Uiso 1 1 calc R . . C20 C 1.0295(5) 0.0871(3) 0.5065(3) 0.0278(9) Uani 1 1 d . . . H20A H 1.0917 0.0787 0.4478 0.033 Uiso 1 1 calc R . . H20B H 1.0812 0.0477 0.5720 0.033 Uiso 1 1 calc R . . C21 C 1.0427(5) 0.1851(3) 0.5441(3) 0.0311(9) Uani 1 1 d . . . H21A H 0.9798 0.1950 0.6022 0.037 Uiso 1 1 calc R . . H21B H 1.1600 0.2015 0.5775 0.037 Uiso 1 1 calc R . . Cl1 Cl 0.51031(10) 0.99335(6) 0.78373(7) 0.0211(2) Uani 1 1 d . . . Cl2 Cl 0.69003(10) 0.85338(6) 0.21647(7) 0.0197(2) Uani 1 1 d . . . H2N H 0.712(6) 0.189(3) 0.328(4) 0.028(13) Uiso 1 1 d . . . H1NA H 0.717(7) 0.002(4) 0.019(4) 0.033(13) Uiso 1 1 d . . . H1NB H 0.818(8) 0.060(4) -0.003(6) 0.06(2) Uiso 1 1 d . . . H1NC H 0.891(7) 0.013(3) 0.094(4) 0.034(12) Uiso 1 1 d . . . N2 N 0.7977(4) 0.0380(2) 0.0458(3) 0.0188(7) Uani 1 1 d . . . N1 N 0.6888(4) 0.1800(2) 0.2636(3) 0.0231(7) Uani 1 1 d . . . O1 O 0.1279(4) 0.0367(2) 0.1986(3) 0.0397(8) Uani 1 1 d . . . O2 O 0.0560(4) -0.0648(2) -0.0052(3) 0.0384(7) Uani 1 1 d . . . O3 O -0.0477(4) 0.0998(3) -0.1214(3) 0.0390(7) Uani 1 1 d . . . O4 O 0.0227(4) 0.2029(2) 0.0805(3) 0.0408(8) Uani 1 1 d . . . O5 O 0.9761(4) 0.2397(2) 0.4469(2) 0.0299(6) Uani 1 1 d . . . O6 O 0.6585(4) 0.30594(19) 0.4429(2) 0.0274(6) Uani 1 1 d . . . O7 O 0.5453(3) 0.13120(18) 0.4534(2) 0.0246(6) Uani 1 1 d . . . O8 O 0.8633(3) 0.05913(19) 0.4620(2) 0.0253(6) Uani 1 1 d . . . O9 O 0.5818(4) 1.08229(19) 0.7814(2) 0.0309(7) Uani 1 1 d . . . O10 O 0.3513(3) 0.9885(2) 0.7055(2) 0.0346(7) Uani 1 1 d . . . O11 O 0.6171(4) 0.9251(2) 0.7543(3) 0.0395(8) Uani 1 1 d . . . O12 O 0.4927(4) 0.9757(2) 0.8972(2) 0.0378(8) Uani 1 1 d . . . O13 O 0.5947(5) 0.9060(3) 0.1258(4) 0.0680(14) Uani 1 1 d . . . O14 O 0.6735(4) 0.7586(2) 0.1847(4) 0.0501(9) Uani 1 1 d . . . O15 O 0.8600(4) 0.8813(2) 0.2369(3) 0.0344(7) Uani 1 1 d . . . O16 O 0.6368(5) 0.8642(3) 0.3172(3) 0.0531(10) 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 C2 0.0128(16) 0.0176(17) 0.0164(17) -0.0027(14) 0.0063(13) -0.0025(13) C1 0.0173(17) 0.0234(18) 0.0148(17) 0.0004(14) 0.0021(14) 0.0006(14) C5 0.0193(17) 0.0220(18) 0.024(2) -0.0078(16) 0.0098(15) 0.0002(14) C4 0.0133(16) 0.0202(18) 0.025(2) 0.0009(15) 0.0034(14) -0.0001(14) C3 0.0169(17) 0.0185(17) 0.0157(16) -0.0020(14) 0.0041(13) -0.0048(13) C6 0.0208(19) 0.036(2) 0.035(2) 0.0161(19) 0.0072(17) 0.0049(17) C7 0.031(2) 0.032(2) 0.067(3) 0.015(2) 0.018(2) 0.0114(19) C8 0.026(2) 0.035(2) 0.028(2) -0.0109(18) 0.0129(17) -0.0038(17) C9 0.030(2) 0.061(3) 0.024(2) -0.006(2) 0.0071(18) -0.001(2) C10 0.027(2) 0.030(2) 0.032(2) 0.0155(18) 0.0116(17) 0.0037(17) C11 0.039(3) 0.030(2) 0.056(3) 0.006(2) 0.021(2) -0.0004(19) C12 0.031(2) 0.035(2) 0.031(2) -0.0112(18) 0.0109(17) -0.0108(18) C13 0.026(2) 0.080(4) 0.033(2) -0.005(3) 0.0023(19) -0.014(2) C14 0.049(3) 0.025(2) 0.025(2) 0.0034(16) 0.0047(18) -0.0127(18) C15 0.056(3) 0.0143(18) 0.023(2) -0.0039(16) 0.0057(18) -0.0006(19) C16 0.040(2) 0.030(2) 0.031(2) 0.0010(18) 0.0166(18) 0.0155(19) C17 0.033(2) 0.029(2) 0.0235(19) -0.0003(17) 0.0144(16) 0.0058(17) C18 0.042(2) 0.020(2) 0.026(2) -0.0015(16) 0.0123(18) -0.0065(17) C19 0.046(2) 0.023(2) 0.0184(19) 0.0073(16) 0.0117(18) 0.0083(18) C20 0.026(2) 0.036(2) 0.0207(19) 0.0032(17) 0.0037(16) 0.0111(17) C21 0.024(2) 0.043(3) 0.023(2) -0.0044(19) -0.0013(15) -0.0004(18) Cl1 0.0180(4) 0.0237(4) 0.0205(4) 0.0007(4) 0.0027(3) -0.0022(3) Cl2 0.0182(4) 0.0249(4) 0.0168(4) 0.0025(3) 0.0057(3) -0.0023(4) N2 0.0166(17) 0.0232(17) 0.0178(17) -0.0007(14) 0.0064(14) 0.0042(14) N1 0.0237(17) 0.0315(19) 0.0130(16) -0.0024(14) 0.0027(13) 0.0010(14) O1 0.0296(16) 0.059(2) 0.0300(16) 0.0067(15) 0.0066(13) -0.0041(15) O2 0.0283(16) 0.0377(18) 0.051(2) -0.0066(15) 0.0133(14) 0.0012(14) O3 0.0274(16) 0.057(2) 0.0330(16) 0.0029(15) 0.0087(13) -0.0018(15) O4 0.0398(18) 0.0349(17) 0.054(2) 0.0011(15) 0.0242(15) 0.0004(14) O5 0.0367(16) 0.0308(15) 0.0224(14) 0.0004(12) 0.0075(12) -0.0067(13) O6 0.0378(16) 0.0260(14) 0.0199(14) -0.0003(11) 0.0098(12) -0.0008(12) O7 0.0279(14) 0.0263(15) 0.0201(13) 0.0035(11) 0.0070(11) 0.0015(11) O8 0.0305(14) 0.0285(15) 0.0161(13) -0.0005(11) 0.0045(11) 0.0009(11) O9 0.0430(17) 0.0252(15) 0.0257(15) -0.0027(12) 0.0110(13) -0.0040(12) O10 0.0197(14) 0.0534(19) 0.0265(14) -0.0113(15) -0.0024(11) 0.0039(13) O11 0.0266(15) 0.0287(16) 0.063(2) -0.0072(15) 0.0108(15) -0.0006(13) O12 0.0354(17) 0.057(2) 0.0197(14) 0.0026(14) 0.0046(12) -0.0236(15) O13 0.049(2) 0.067(3) 0.070(3) 0.049(2) -0.018(2) -0.020(2) O14 0.0437(19) 0.0354(18) 0.073(3) -0.0219(18) 0.0175(18) -0.0084(15) O15 0.0218(14) 0.0390(18) 0.0417(17) -0.0075(14) 0.0068(12) -0.0029(12) O16 0.061(2) 0.066(3) 0.0446(19) -0.0220(19) 0.0366(18) -0.018(2) _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 C2 C1 1.371(5) . ? C2 C3 1.383(5) . ? C2 N2 1.463(5) . ? C1 N1 1.343(5) . ? C1 H1 0.9500 . ? C5 N1 1.344(5) . ? C5 C4 1.366(5) . ? C5 H5 0.9500 . ? C4 C3 1.392(5) . ? C4 H4 0.9500 . ? C3 H3 0.9500 . ? C6 O1 1.450(5) . ? C6 C7 1.525(7) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 O2 1.408(6) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 O2 1.426(5) . ? C8 C9 1.532(7) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 O3 1.402(6) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 O3 1.432(6) . ? C10 C11 1.517(7) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 O4 1.417(6) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 O4 1.423(5) . ? C12 C13 1.552(8) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 O1 1.390(6) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 O5 1.441(5) . ? C14 C15 1.490(7) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 O6 1.416(5) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 O6 1.414(5) . ? C16 C17 1.500(6) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 O7 1.422(5) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 O7 1.428(5) . ? C18 C19 1.489(6) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 O8 1.437(5) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 O8 1.416(5) . ? C20 C21 1.500(6) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 O5 1.419(5) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? Cl1 O10 1.427(3) . ? Cl1 O9 1.433(3) . ? Cl1 O11 1.441(3) . ? Cl1 O12 1.447(3) . ? Cl2 O16 1.412(3) . ? Cl2 O13 1.415(3) . ? Cl2 O15 1.435(3) . ? Cl2 O14 1.436(3) . ? N2 H1NA 0.85(6) . ? N2 H1NB 0.73(7) . ? N2 H1NC 0.92(5) . ? N1 H2N 0.77(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 C2 C3 121.5(3) . . ? C1 C2 N2 118.0(3) . . ? C3 C2 N2 120.5(3) . . ? N1 C1 C2 118.0(3) . . ? N1 C1 H1 121.0 . . ? C2 C1 H1 121.0 . . ? N1 C5 C4 119.9(3) . . ? N1 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C4 C3 119.5(3) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C2 C3 C4 118.2(3) . . ? C2 C3 H3 120.9 . . ? C4 C3 H3 120.9 . . ? O1 C6 C7 112.0(3) . . ? O1 C6 H6A 109.2 . . ? C7 C6 H6A 109.2 . . ? O1 C6 H6B 109.2 . . ? C7 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? O2 C7 C6 107.7(4) . . ? O2 C7 H7A 110.2 . . ? C6 C7 H7A 110.2 . . ? O2 C7 H7B 110.2 . . ? C6 C7 H7B 110.2 . . ? H7A C7 H7B 108.5 . . ? O2 C8 C9 111.9(3) . . ? O2 C8 H8A 109.2 . . ? C9 C8 H8A 109.2 . . ? O2 C8 H8B 109.2 . . ? C9 C8 H8B 109.2 . . ? H8A C8 H8B 107.9 . . ? O3 C9 C8 106.7(4) . . ? O3 C9 H9A 110.4 . . ? C8 C9 H9A 110.4 . . ? O3 C9 H9B 110.4 . . ? C8 C9 H9B 110.4 . . ? H9A C9 H9B 108.6 . . ? O3 C10 C11 112.4(3) . . ? O3 C10 H10A 109.1 . . ? C11 C10 H10A 109.1 . . ? O3 C10 H10B 109.1 . . ? C11 C10 H10B 109.1 . . ? H10A C10 H10B 107.8 . . ? O4 C11 C10 107.0(4) . . ? O4 C11 H11A 110.3 . . ? C10 C11 H11A 110.3 . . ? O4 C11 H11B 110.3 . . ? C10 C11 H11B 110.3 . . ? H11A C11 H11B 108.6 . . ? O4 C12 C13 112.2(3) . . ? O4 C12 H12A 109.2 . . ? C13 C12 H12A 109.2 . . ? O4 C12 H12B 109.2 . . ? C13 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? O1 C13 C12 106.5(4) . . ? O1 C13 H13A 110.4 . . ? C12 C13 H13A 110.4 . . ? O1 C13 H13B 110.4 . . ? C12 C13 H13B 110.4 . . ? H13A C13 H13B 108.6 . . ? O5 C14 C15 112.4(3) . . ? O5 C14 H14A 109.1 . . ? C15 C14 H14A 109.1 . . ? O5 C14 H14B 109.1 . . ? C15 C14 H14B 109.1 . . ? H14A C14 H14B 107.9 . . ? O6 C15 C14 108.3(3) . . ? O6 C15 H15A 110.0 . . ? C14 C15 H15A 110.0 . . ? O6 C15 H15B 110.0 . . ? C14 C15 H15B 110.0 . . ? H15A C15 H15B 108.4 . . ? O6 C16 C17 110.6(3) . . ? O6 C16 H16A 109.5 . . ? C17 C16 H16A 109.5 . . ? O6 C16 H16B 109.5 . . ? C17 C16 H16B 109.5 . . ? H16A C16 H16B 108.1 . . ? O7 C17 C16 107.2(3) . . ? O7 C17 H17A 110.3 . . ? C16 C17 H17A 110.3 . . ? O7 C17 H17B 110.3 . . ? C16 C17 H17B 110.3 . . ? H17A C17 H17B 108.5 . . ? O7 C18 C19 113.5(3) . . ? O7 C18 H18A 108.9 . . ? C19 C18 H18A 108.9 . . ? O7 C18 H18B 108.9 . . ? C19 C18 H18B 108.9 . . ? H18A C18 H18B 107.7 . . ? O8 C19 C18 107.4(3) . . ? O8 C19 H19A 110.2 . . ? C18 C19 H19A 110.2 . . ? O8 C19 H19B 110.2 . . ? C18 C19 H19B 110.2 . . ? H19A C19 H19B 108.5 . . ? O8 C20 C21 112.5(3) . . ? O8 C20 H20A 109.1 . . ? C21 C20 H20A 109.1 . . ? O8 C20 H20B 109.1 . . ? C21 C20 H20B 109.1 . . ? H20A C20 H20B 107.8 . . ? O5 C21 C20 107.5(3) . . ? O5 C21 H21A 110.2 . . ? C20 C21 H21A 110.2 . . ? O5 C21 H21B 110.2 . . ? C20 C21 H21B 110.2 . . ? H21A C21 H21B 108.5 . . ? O10 Cl1 O9 110.7(2) . . ? O10 Cl1 O11 109.19(19) . . ? O9 Cl1 O11 109.74(18) . . ? O10 Cl1 O12 109.13(19) . . ? O9 Cl1 O12 108.80(18) . . ? O11 Cl1 O12 109.2(2) . . ? O16 Cl2 O13 112.2(3) . . ? O16 Cl2 O15 109.2(2) . . ? O13 Cl2 O15 108.5(2) . . ? O16 Cl2 O14 108.2(2) . . ? O13 Cl2 O14 108.5(3) . . ? O15 Cl2 O14 110.20(19) . . ? C2 N2 H1NA 103(3) . . ? C2 N2 H1NB 105(5) . . ? H1NA N2 H1NB 107(6) . . ? C2 N2 H1NC 113(3) . . ? H1NA N2 H1NC 118(4) . . ? H1NB N2 H1NC 111(6) . . ? C1 N1 C5 122.9(3) . . ? C1 N1 H2N 124(4) . . ? C5 N1 H2N 113(4) . . ? C13 O1 C6 111.5(4) . . ? C7 O2 C8 112.7(3) . . ? C9 O3 C10 113.3(3) . . ? C11 O4 C12 114.3(3) . . ? C21 O5 C14 114.6(3) . . ? C16 O6 C15 113.8(3) . . ? C17 O7 C18 114.4(3) . . ? C20 O8 C19 114.8(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 C20 H20B O10 0.99 2.58 3.448(5) 147.1 1_645 C18 H18A O16 0.99 2.52 3.417(5) 150.7 1_545 C5 H5 O11 0.95 2.40 3.266(5) 152.2 2_646 C4 H4 O13 0.95 2.61 3.490(6) 155.1 2_645 C3 H3 O9 0.95 2.45 3.293(4) 147.7 1_544 N2 H1NA O12 0.85(6) 2.11(5) 2.875(5) 149(4) 1_544 N2 H1NB O3 0.73(7) 2.12(7) 2.815(5) 161(7) 1_655 N2 H1NC O1 0.92(5) 2.09(5) 2.911(5) 147(4) 1_655 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.065 _refine_diff_density_min -0.319 _refine_diff_density_rms 0.076 #END********************************************************************** data_3AP-B15C5 _database_code_depnum_ccdc_archive 'CCDC 846228' #TrackingRef '- Structures(3).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C14 H20 O5),2(C5 H8 N2), 4(Cl O4), 2(H2 O)' _chemical_formula_sum 'C38 H60 Cl4 N4 O28' _chemical_formula_weight 1162.70 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 17.7353(14) _cell_length_b 15.4444(12) _cell_length_c 19.7642(16) _cell_angle_alpha 90.00 _cell_angle_beta 112.756(1) _cell_angle_gamma 90.00 _cell_volume 4992.2(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7692 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 26.00 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.542 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2424 _exptl_absorpt_coefficient_mu 0.334 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9065 _exptl_absorpt_correction_T_max 0.9547 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD 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 47292 _diffrn_reflns_av_R_equivalents 0.0419 _diffrn_reflns_av_sigmaI/netI 0.0301 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.31 _diffrn_reflns_theta_max 25.00 _reflns_number_total 8790 _reflns_number_gt 7709 _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^)+(0.0575P)^2^+13.4466P] 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 8790 _refine_ls_number_parameters 754 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0732 _refine_ls_R_factor_gt 0.0647 _refine_ls_wR_factor_ref 0.1559 _refine_ls_wR_factor_gt 0.1502 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7304(2) 0.1783(2) 0.41367(18) 0.0265(8) Uani 1 1 d . . . C2 C 0.6911(3) 0.1019(2) 0.38463(19) 0.0364(9) Uani 1 1 d . . . H2 H 0.6346 0.0949 0.3747 0.044 Uiso 1 1 calc R . . C3 C 0.7354(3) 0.0345(2) 0.3698(2) 0.0448(12) Uani 1 1 d . . . H3 H 0.7087 -0.0185 0.3505 0.054 Uiso 1 1 calc R . . C4 C 0.8164(3) 0.0440(3) 0.3828(2) 0.0446(11) Uani 1 1 d . . . H4 H 0.8454 -0.0024 0.3723 0.053 Uiso 1 1 calc R . . C5 C 0.8565(3) 0.1210(3) 0.4113(2) 0.0364(9) Uani 1 1 d . . . H5 H 0.9126 0.1281 0.4193 0.044 Uiso 1 1 calc R . . C6 C 0.8139(2) 0.1874(2) 0.42777(18) 0.0262(8) Uani 1 1 d . . . C7 C 0.9319(2) 0.2788(3) 0.4826(2) 0.0304(8) Uani 1 1 d . . . H7A H 0.9488 0.2857 0.4408 0.036 Uiso 1 1 calc R . . H7B H 0.9616 0.2290 0.5127 0.036 Uiso 1 1 calc R . . C8 C 0.9488(2) 0.3592(3) 0.5276(2) 0.0333(9) Uani 1 1 d . . . H8A H 0.9313 0.3518 0.5691 0.040 Uiso 1 1 calc R . . H8B H 1.0081 0.3719 0.5477 0.040 Uiso 1 1 calc R . . C9 C 0.9048(2) 0.5059(3) 0.5223(2) 0.0354(9) Uani 1 1 d . . . H9A H 0.8923 0.5563 0.4889 0.042 Uiso 1 1 calc R . . H9B H 0.9603 0.5143 0.5604 0.042 Uiso 1 1 calc R . . C10 C 0.8445(2) 0.5032(3) 0.5586(2) 0.0371(9) Uani 1 1 d . . . H10A H 0.8554 0.4523 0.5915 0.044 Uiso 1 1 calc R . . H10B H 0.8495 0.5561 0.5882 0.044 Uiso 1 1 calc R . . C11 C 0.7026(2) 0.4859(3) 0.5317(2) 0.0344(9) Uani 1 1 d . . . H11A H 0.7027 0.5355 0.5634 0.041 Uiso 1 1 calc R . . H11B H 0.7134 0.4323 0.5615 0.041 Uiso 1 1 calc R . . C12 C 0.6217(2) 0.4796(3) 0.4685(2) 0.0345(9) Uani 1 1 d . . . H12A H 0.5777 0.4753 0.4875 0.041 Uiso 1 1 calc R . . H12B H 0.6124 0.5329 0.4385 0.041 Uiso 1 1 calc R . . C13 C 0.5931(3) 0.3286(3) 0.4492(2) 0.0406(10) Uani 1 1 d . . . H13A H 0.5339 0.3315 0.4390 0.049 Uiso 1 1 calc R . . H13B H 0.6232 0.3237 0.5030 0.049 Uiso 1 1 calc R . . C14 C 0.6102(2) 0.2509(3) 0.4122(2) 0.0354(9) Uani 1 1 d . . . H14A H 0.5920 0.1975 0.4290 0.042 Uiso 1 1 calc R . . H14B H 0.5812 0.2555 0.3583 0.042 Uiso 1 1 calc R . . C15 C 0.7269(3) 0.5930(3) 0.8802(2) 0.0351(9) Uani 1 1 d . . . C16 C 0.7092(3) 0.6745(3) 0.8504(2) 0.0477(12) Uani 1 1 d . . . H16 H 0.6538 0.6915 0.8253 0.057 Uiso 1 1 calc R . . C17 C 0.7714(4) 0.7319(3) 0.8569(3) 0.0557(14) Uani 1 1 d . . . H17 H 0.7589 0.7884 0.8366 0.067 Uiso 1 1 calc R . . C18 C 0.8512(4) 0.7067(3) 0.8927(3) 0.0550(14) Uani 1 1 d . . . H18 H 0.8939 0.7451 0.8947 0.066 Uiso 1 1 calc R . . C19 C 0.8708(3) 0.6261(3) 0.9259(2) 0.0438(11) Uani 1 1 d . . . H19 H 0.9263 0.6100 0.9516 0.053 Uiso 1 1 calc R . . C20 C 0.8082(3) 0.5690(2) 0.9213(2) 0.0346(9) Uani 1 1 d . . . C21 C 0.9006(2) 0.4677(3) 1.0035(2) 0.0370(9) Uani 1 1 d . . . H21A H 0.9248 0.5162 1.0378 0.044 Uiso 1 1 calc R . . H21B H 0.9357 0.4558 0.9759 0.044 Uiso 1 1 calc R . . C22 C 0.8941(2) 0.3889(3) 1.0448(2) 0.0366(9) Uani 1 1 d . . . H22A H 0.9482 0.3748 1.0832 0.044 Uiso 1 1 calc R . . H22B H 0.8554 0.3998 1.0689 0.044 Uiso 1 1 calc R . . C23 C 0.8572(2) 0.2399(3) 1.0293(2) 0.0374(9) Uani 1 1 d . . . H23A H 0.9046 0.2336 1.0765 0.045 Uiso 1 1 calc R . . H23B H 0.8578 0.1903 0.9977 0.045 Uiso 1 1 calc R . . C24 C 0.7798(2) 0.2369(3) 1.0434(2) 0.0339(9) Uani 1 1 d . . . H24A H 0.7776 0.1827 1.0693 0.041 Uiso 1 1 calc R . . H24B H 0.7779 0.2865 1.0745 0.041 Uiso 1 1 calc R . . C25 C 0.6365(2) 0.2558(2) 0.9817(2) 0.0285(8) Uani 1 1 d . . . H25A H 0.6386 0.2302 1.0283 0.034 Uiso 1 1 calc R . . H25B H 0.5921 0.2266 0.9410 0.034 Uiso 1 1 calc R . . C26 C 0.6173(2) 0.3509(2) 0.9806(2) 0.0306(8) Uani 1 1 d . . . H26A H 0.5706 0.3599 0.9955 0.037 Uiso 1 1 calc R . . H26B H 0.6651 0.3826 1.0152 0.037 Uiso 1 1 calc R . . C27 C 0.5617(2) 0.4669(3) 0.8942(2) 0.0402(10) Uani 1 1 d . . . H27A H 0.5263 0.4736 0.9222 0.048 Uiso 1 1 calc R . . H27B H 0.5267 0.4725 0.8415 0.048 Uiso 1 1 calc R . . C28 C 0.6232(2) 0.5378(2) 0.9152(2) 0.0321(8) Uani 1 1 d . . . H28A H 0.5957 0.5948 0.9090 0.039 Uiso 1 1 calc R . . H28B H 0.6611 0.5316 0.9671 0.039 Uiso 1 1 calc R . . C29 C 0.2196(2) 0.2338(2) 0.32957(18) 0.0290(8) Uani 1 1 d . . . C30 C 0.1465(3) 0.2770(3) 0.2986(2) 0.0389(10) Uani 1 1 d . . . H30 H 0.0971 0.2500 0.2954 0.047 Uiso 1 1 calc R . . C31 C 0.1454(4) 0.3587(3) 0.2727(2) 0.0559(14) Uani 1 1 d . . . H31 H 0.0951 0.3891 0.2515 0.067 Uiso 1 1 calc R . . C32 C 0.2159(5) 0.3966(3) 0.2771(2) 0.0673(18) Uani 1 1 d . . . H32 H 0.2153 0.4533 0.2583 0.081 Uiso 1 1 calc R . . C33 C 0.2902(3) 0.2724(3) 0.3345(2) 0.0410(10) Uani 1 1 d . . . H33 H 0.3409 0.2428 0.3561 0.049 Uiso 1 1 calc R . . C34 C 0.26354(19) 0.5135(2) 0.66389(16) 0.0179(6) Uani 1 1 d . . . C35 C 0.3360(2) 0.4670(2) 0.68852(17) 0.0215(7) Uani 1 1 d . . . H35 H 0.3837 0.4902 0.6845 0.026 Uiso 1 1 calc R . . C36 C 0.3375(2) 0.3862(2) 0.71904(18) 0.0247(7) Uani 1 1 d . . . H36 H 0.3863 0.3528 0.7357 0.030 Uiso 1 1 calc R . . C37 C 0.2680(2) 0.3543(2) 0.72526(18) 0.0253(7) Uani 1 1 d . . . H37 H 0.2684 0.2989 0.7463 0.030 Uiso 1 1 calc R . . C38 C 0.1955(2) 0.4803(2) 0.67120(17) 0.0190(7) Uani 1 1 d . . . H38 H 0.1459 0.5123 0.6551 0.023 Uiso 1 1 calc R . . Cl1 Cl 0.08798(5) 0.18813(5) 0.69187(4) 0.0243(2) Uani 1 1 d . . . Cl2 Cl 0.08111(5) 0.66090(5) 0.72147(4) 0.0263(2) Uani 1 1 d . . . Cl3 Cl 0.41805(5) 0.10185(6) 0.30605(5) 0.0314(2) Uani 1 1 d . . . Cl4 Cl 0.07659(6) 0.06200(8) 0.16874(5) 0.0443(3) Uani 1 1 d . . . H4N H 0.156(3) 0.385(3) 0.706(2) 0.035(11) Uiso 1 1 d . . . H1NA H 0.178(3) 0.135(3) 0.375(3) 0.065(16) Uiso 1 1 d . . . H3NA H 0.294(2) 0.602(3) 0.607(2) 0.030(10) Uiso 1 1 d . . . H1NB H 0.266(3) 0.147(3) 0.390(3) 0.040 Uiso 1 1 d . . . H3NB H 0.210(3) 0.609(2) 0.599(2) 0.025(10) Uiso 1 1 d . . . H1NC H 0.228(4) 0.115(4) 0.322(4) 0.10(2) Uiso 1 1 d . . . H3NC H 0.272(2) 0.638(3) 0.665(2) 0.028(10) Uiso 1 1 d . . . N1 N 0.2212(3) 0.1459(2) 0.3568(2) 0.0430(9) Uani 1 1 d . . . N2 N 0.2873(3) 0.3530(3) 0.30845(19) 0.0595(12) Uani 1 1 d . . . N3 N 0.25982(19) 0.59851(18) 0.63149(17) 0.0190(6) Uani 1 1 d . . . N4 N 0.20016(19) 0.40208(18) 0.70141(15) 0.0228(6) Uani 1 1 d . . . O1 O 0.69672(14) 0.24936(15) 0.43188(13) 0.0274(5) Uani 1 1 d . . . O2 O 0.84590(14) 0.26590(16) 0.45736(13) 0.0284(6) Uani 1 1 d . . . O3 O 0.90431(14) 0.42920(16) 0.48152(12) 0.0276(5) Uani 1 1 d . . . O4 O 0.76399(15) 0.49745(16) 0.50256(13) 0.0301(6) Uani 1 1 d . . . O5 O 0.61791(15) 0.40549(16) 0.42298(13) 0.0281(6) Uani 1 1 d . . . O6 O 0.66684(17) 0.53128(17) 0.86821(14) 0.0350(6) Uani 1 1 d . . . O7 O 0.81928(15) 0.48939(17) 0.95380(14) 0.0329(6) Uani 1 1 d . . . O8 O 0.86577(16) 0.31845(17) 0.99468(14) 0.0341(6) Uani 1 1 d . . . O9 O 0.71239(15) 0.24074(16) 0.97456(13) 0.0289(6) Uani 1 1 d . . . O10 O 0.59725(16) 0.38168(16) 0.90734(14) 0.0330(6) Uani 1 1 d . . . O11 O 0.14952(15) 0.22350(16) 0.75803(13) 0.0293(6) Uani 1 1 d . . . O12 O 0.00878(15) 0.21784(17) 0.68565(16) 0.0392(7) Uani 1 1 d . . . O13 O 0.09130(18) 0.09657(18) 0.69534(17) 0.0479(8) Uani 1 1 d . . . O14 O 0.10431(18) 0.2191(2) 0.63071(14) 0.0476(8) Uani 1 1 d . . . O15 O 0.15544(18) 0.66600(19) 0.70893(19) 0.0503(8) Uani 1 1 d . . . O19A O 0.4519(3) 0.1372(3) 0.3801(2) 0.0624(16) Uani 0.809(9) 1 d P . . O19B O 0.3916(11) 0.0961(19) 0.2232(9) 0.072(9) Uani 0.191(9) 1 d P . . O20A O 0.4233(2) 0.1645(3) 0.2576(2) 0.0463(17) Uani 0.836(12) 1 d P . . O20B O 0.4825(12) 0.066(2) 0.3435(16) 0.060(10) Uani 0.164(12) 1 d P . . O21A O 0.4657(3) 0.0263(3) 0.3058(4) 0.0516(14) Uani 0.843(11) 1 d P . . O21B O 0.4304(10) 0.2029(12) 0.3116(11) 0.038(7) Uani 0.157(11) 1 d P . . O22 O 0.33747(18) 0.0784(2) 0.2954(2) 0.0612(10) Uani 1 1 d . . . O23 O 0.1597(3) 0.0726(4) 0.2135(2) 0.111(2) Uani 1 1 d . . . O24 O 0.0263(2) 0.0490(4) 0.2019(2) 0.111(2) Uani 1 1 d . . . O25 O 0.0475(3) 0.1045(4) 0.1033(2) 0.123(2) Uani 1 1 d . . . O27 O 0.04847(14) 0.40313(16) 0.70290(13) 0.0273(5) Uani 1 1 d . . . O26A O 0.0742(4) -0.0473(5) 0.1598(4) 0.0645(19) Uiso 0.50 1 d P . . O16A O 0.0385(3) 0.5854(3) 0.6889(3) 0.0365(14) Uani 0.773(12) 1 d P . . O17A O 0.0997(3) 0.6674(3) 0.7963(2) 0.0513(17) Uani 0.777(12) 1 d P . . O17B O 0.0088(11) 0.6291(14) 0.6625(9) 0.058(6) Uani 0.223(12) 1 d P . . O18A O 0.0339(2) 0.7367(2) 0.68428(18) 0.0359(10) Uani 0.802(7) 1 d P . . O16B O 0.0561(10) 0.7168(10) 0.7670(9) 0.051(6) Uani 0.227(12) 1 d P . . O18B O 0.0973(9) 0.5758(9) 0.7730(7) 0.038(4) Uani 0.198(7) 1 d P . . O26B O 0.0905(5) -0.0013(6) 0.1256(5) 0.081(2) Uiso 0.50 1 d P . . O28 O 0.0559(3) -0.1472(3) 0.1963(3) 0.060(2) Uani 0.602(11) 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.037(2) 0.0224(18) 0.0172(16) 0.0065(13) 0.0070(15) 0.0023(15) C2 0.053(3) 0.030(2) 0.0220(18) 0.0077(15) 0.0103(18) -0.0084(18) C3 0.091(4) 0.0167(19) 0.026(2) 0.0023(15) 0.021(2) -0.004(2) C4 0.083(4) 0.026(2) 0.028(2) 0.0078(17) 0.025(2) 0.018(2) C5 0.052(3) 0.034(2) 0.0232(18) 0.0099(16) 0.0146(18) 0.0185(19) C6 0.033(2) 0.0237(18) 0.0170(16) 0.0060(14) 0.0045(15) 0.0050(15) C7 0.0191(17) 0.044(2) 0.0254(18) 0.0077(16) 0.0059(14) 0.0099(16) C8 0.0203(18) 0.050(2) 0.0232(18) 0.0057(17) 0.0010(15) -0.0017(16) C9 0.037(2) 0.036(2) 0.030(2) -0.0093(17) 0.0091(17) -0.0124(17) C10 0.046(2) 0.038(2) 0.0241(19) -0.0097(16) 0.0096(17) -0.0079(18) C11 0.047(2) 0.038(2) 0.0268(19) 0.0025(16) 0.0229(18) 0.0126(18) C12 0.039(2) 0.039(2) 0.036(2) 0.0081(17) 0.0256(18) 0.0158(18) C13 0.038(2) 0.043(2) 0.054(3) 0.014(2) 0.033(2) 0.0013(18) C14 0.027(2) 0.034(2) 0.049(2) 0.0117(18) 0.0182(18) -0.0055(16) C15 0.052(3) 0.032(2) 0.031(2) -0.0075(16) 0.0264(19) -0.0050(18) C16 0.083(3) 0.031(2) 0.044(2) -0.0010(19) 0.041(2) 0.005(2) C17 0.110(5) 0.026(2) 0.055(3) -0.006(2) 0.058(3) -0.003(3) C18 0.100(4) 0.036(2) 0.056(3) -0.017(2) 0.060(3) -0.024(3) C19 0.061(3) 0.042(2) 0.041(2) -0.0138(19) 0.035(2) -0.018(2) C20 0.051(2) 0.030(2) 0.032(2) -0.0087(16) 0.0272(19) -0.0111(18) C21 0.029(2) 0.043(2) 0.040(2) -0.0088(18) 0.0149(18) -0.0131(17) C22 0.026(2) 0.048(2) 0.033(2) -0.0052(18) 0.0095(17) -0.0047(17) C23 0.034(2) 0.038(2) 0.039(2) 0.0035(18) 0.0129(18) 0.0051(17) C24 0.036(2) 0.038(2) 0.0257(19) 0.0066(16) 0.0103(17) -0.0022(17) C25 0.0302(19) 0.0278(19) 0.0284(19) 0.0025(15) 0.0124(16) -0.0048(15) C26 0.032(2) 0.032(2) 0.0282(19) 0.0000(15) 0.0120(16) -0.0037(16) C27 0.033(2) 0.034(2) 0.048(2) 0.0069(18) 0.0095(19) 0.0043(17) C28 0.040(2) 0.028(2) 0.033(2) 0.0071(16) 0.0193(17) 0.0096(16) C29 0.043(2) 0.030(2) 0.0167(16) 0.0016(14) 0.0148(16) 0.0087(17) C30 0.048(2) 0.050(3) 0.0238(19) 0.0047(18) 0.0202(18) 0.017(2) C31 0.095(4) 0.050(3) 0.036(2) 0.016(2) 0.040(3) 0.036(3) C32 0.158(6) 0.029(2) 0.025(2) 0.0043(19) 0.046(3) 0.007(3) C33 0.042(2) 0.058(3) 0.0212(19) 0.0017(18) 0.0112(17) 0.000(2) C34 0.0243(17) 0.0157(16) 0.0146(15) -0.0019(12) 0.0086(13) -0.0002(13) C35 0.0219(17) 0.0239(18) 0.0209(16) -0.0019(13) 0.0106(14) 0.0000(13) C36 0.0311(19) 0.0202(17) 0.0222(17) 0.0018(14) 0.0097(15) 0.0061(14) C37 0.040(2) 0.0158(16) 0.0204(17) -0.0008(13) 0.0115(15) -0.0015(15) C38 0.0216(17) 0.0186(16) 0.0170(15) -0.0014(12) 0.0077(13) 0.0010(13) Cl1 0.0242(4) 0.0196(4) 0.0241(4) -0.0019(3) 0.0038(3) 0.0022(3) Cl2 0.0252(4) 0.0243(4) 0.0245(4) -0.0063(3) 0.0043(3) 0.0025(3) Cl3 0.0260(5) 0.0330(5) 0.0399(5) -0.0003(4) 0.0181(4) -0.0051(4) Cl4 0.0334(5) 0.0672(7) 0.0329(5) -0.0095(5) 0.0134(4) -0.0280(5) N1 0.074(3) 0.0323(19) 0.0326(19) 0.0061(16) 0.0312(19) 0.0163(19) N2 0.093(3) 0.062(3) 0.0243(18) -0.0073(19) 0.023(2) -0.032(3) N3 0.0217(16) 0.0172(14) 0.0198(15) 0.0007(12) 0.0099(13) 0.0016(12) N4 0.0283(16) 0.0206(15) 0.0224(15) -0.0027(12) 0.0130(13) -0.0067(13) O1 0.0253(13) 0.0234(13) 0.0324(13) 0.0037(10) 0.0100(11) 0.0006(10) O2 0.0222(12) 0.0287(13) 0.0289(13) -0.0005(11) 0.0040(10) 0.0046(10) O3 0.0243(13) 0.0337(14) 0.0213(12) -0.0006(10) 0.0049(10) -0.0042(10) O4 0.0377(15) 0.0328(14) 0.0226(13) -0.0031(11) 0.0149(11) 0.0009(11) O5 0.0286(13) 0.0307(14) 0.0308(13) 0.0075(11) 0.0181(11) 0.0062(11) O6 0.0448(16) 0.0347(15) 0.0284(14) -0.0056(11) 0.0174(12) -0.0051(12) O7 0.0315(14) 0.0340(15) 0.0344(14) -0.0019(11) 0.0142(12) -0.0096(11) O8 0.0323(14) 0.0384(15) 0.0349(14) -0.0025(12) 0.0165(12) -0.0046(12) O9 0.0307(14) 0.0323(14) 0.0244(12) 0.0028(10) 0.0115(11) -0.0015(11) O10 0.0356(15) 0.0282(14) 0.0311(14) 0.0044(11) 0.0085(12) 0.0009(11) O11 0.0279(13) 0.0308(14) 0.0239(13) -0.0005(10) 0.0043(11) 0.0012(11) O12 0.0225(13) 0.0285(14) 0.0602(18) -0.0023(13) 0.0089(13) 0.0002(11) O13 0.0466(18) 0.0220(14) 0.061(2) -0.0050(13) 0.0058(15) 0.0043(12) O14 0.0477(18) 0.068(2) 0.0218(14) 0.0050(13) 0.0075(13) 0.0013(15) O15 0.0419(17) 0.0408(17) 0.078(2) -0.0150(16) 0.0336(17) -0.0124(14) O19A 0.081(3) 0.056(3) 0.042(2) -0.008(2) 0.015(2) -0.023(2) O19B 0.045(11) 0.15(3) 0.027(9) 0.000(11) 0.021(8) -0.001(12) O20A 0.051(2) 0.041(3) 0.057(3) 0.016(2) 0.031(2) 0.0124(18) O20B 0.019(10) 0.07(2) 0.064(18) 0.033(15) -0.011(11) 0.002(11) O21A 0.042(3) 0.034(2) 0.087(4) 0.016(2) 0.035(3) 0.0105(19) O21B 0.025(10) 0.050(12) 0.043(13) 0.000(9) 0.018(8) -0.009(8) O22 0.0335(17) 0.0456(19) 0.118(3) -0.0069(19) 0.0443(19) -0.0063(14) O23 0.077(3) 0.200(6) 0.041(2) -0.005(3) 0.007(2) -0.075(3) O24 0.058(2) 0.230(6) 0.066(3) 0.076(3) 0.045(2) 0.074(3) O25 0.108(4) 0.192(6) 0.038(2) 0.033(3) -0.006(2) -0.106(4) O27 0.0275(13) 0.0265(13) 0.0292(13) 0.0003(10) 0.0125(11) 0.0010(10) O16A 0.032(2) 0.021(2) 0.057(3) -0.007(2) 0.018(2) -0.0067(18) O17A 0.076(3) 0.052(3) 0.023(2) 0.0033(19) 0.016(2) 0.011(3) O17B 0.064(11) 0.042(11) 0.043(9) -0.002(8) -0.007(8) 0.005(9) O18A 0.035(2) 0.0261(19) 0.038(2) 0.0027(14) 0.0047(15) 0.0051(14) O16B 0.052(10) 0.039(10) 0.066(11) -0.014(8) 0.029(9) -0.011(8) O18B 0.051(9) 0.032(8) 0.026(7) 0.008(6) 0.008(6) 0.009(6) O28 0.042(3) 0.042(3) 0.067(4) 0.018(3) -0.011(3) -0.007(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.362(4) . ? C1 C2 1.378(5) . ? C1 C6 1.404(5) . ? C2 C3 1.401(6) . ? C2 H2 0.9500 . ? C3 C4 1.365(7) . ? C3 H3 0.9500 . ? C4 C5 1.389(6) . ? C4 H4 0.9500 . ? C5 C6 1.385(5) . ? C5 H5 0.9500 . ? C6 O2 1.370(4) . ? C7 O2 1.423(4) . ? C7 C8 1.489(5) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 O3 1.436(4) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 O3 1.431(4) . ? C9 C10 1.500(6) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 O4 1.431(5) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 O4 1.426(4) . ? C11 C12 1.497(6) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 O5 1.441(5) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 O5 1.432(4) . ? C13 C14 1.496(6) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 O1 1.429(4) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.373(6) . ? C15 O6 1.380(5) . ? C15 C20 1.404(6) . ? C16 C17 1.383(7) . ? C16 H16 0.9500 . ? C17 C18 1.372(8) . ? C17 H17 0.9500 . ? C18 C19 1.387(7) . ? C18 H18 0.9500 . ? C19 C20 1.392(6) . ? C19 H19 0.9500 . ? C20 O7 1.366(5) . ? C21 O7 1.435(5) . ? C21 C22 1.495(6) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 O8 1.426(5) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 O8 1.429(5) . ? C23 C24 1.504(5) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 O9 1.423(4) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 O9 1.426(4) . ? C25 C26 1.506(5) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 O10 1.433(4) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 O10 1.439(5) . ? C27 C28 1.487(6) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 O6 1.424(4) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 C33 1.356(6) . ? C29 C30 1.375(5) . ? C29 N1 1.456(5) . ? C30 C31 1.359(6) . ? C30 H30 0.9500 . ? C31 C32 1.353(8) . ? C31 H31 0.9500 . ? C32 N2 1.354(8) . ? C32 H32 0.9500 . ? C33 N2 1.340(6) . ? C33 H33 0.9500 . ? C34 C38 1.369(4) . ? C34 C35 1.386(5) . ? C34 N3 1.450(4) . ? C35 C36 1.382(5) . ? C35 H35 0.9500 . ? C36 C37 1.376(5) . ? C36 H36 0.9500 . ? C37 N4 1.333(5) . ? C37 H37 0.9500 . ? C38 N4 1.336(4) . ? C38 H38 0.9500 . ? Cl1 O13 1.416(3) . ? Cl1 O14 1.430(3) . ? Cl1 O12 1.437(3) . ? Cl1 O11 1.448(2) . ? Cl2 O17A 1.389(4) . ? Cl2 O16A 1.404(4) . ? Cl2 O15 1.435(3) . ? Cl2 O16B 1.436(14) . ? Cl2 O17B 1.445(15) . ? Cl2 O18A 1.461(3) . ? Cl2 O18B 1.618(13) . ? Cl3 O20B 1.23(2) . ? Cl3 O20A 1.391(4) . ? Cl3 O22 1.409(3) . ? Cl3 O21A 1.442(4) . ? Cl3 O19A 1.457(4) . ? Cl3 O19B 1.522(16) . ? Cl3 O21B 1.574(19) . ? Cl4 O24 1.310(4) . ? Cl4 O25 1.362(4) . ? Cl4 O26B 1.381(9) . ? Cl4 O23 1.405(4) . ? Cl4 O26A 1.696(8) . ? N1 H1NA 0.98(6) . ? N1 H1NB 0.81(5) . ? N1 H1NC 0.87(7) . ? N3 H3NA 0.90(4) . ? N3 H3NB 0.88(4) . ? N3 H3NC 0.87(4) . ? N4 H4N 0.86(4) . ? O19A O20B 1.53(4) . ? O19A O21B 1.616(18) . ? O19B O20A 1.27(3) . ? O20A O21B 1.18(2) . ? O20B O21A 0.92(3) . ? O26A O26B 1.095(10) . ? O16A O17B 0.891(19) . ? O16A O18B 1.591(14) . ? O17A O16B 1.082(17) . ? O17A O18B 1.483(14) . ? O17B O18A 1.730(19) . ? O18A O16B 1.557(18) . ? 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 O1 C1 C2 126.6(4) . . ? O1 C1 C6 113.8(3) . . ? C2 C1 C6 119.5(4) . . ? C1 C2 C3 119.2(4) . . ? C1 C2 H2 120.4 . . ? C3 C2 H2 120.4 . . ? C4 C3 C2 121.1(4) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C5 120.3(4) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C6 C5 C4 119.2(4) . . ? C6 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? O2 C6 C5 125.6(3) . . ? O2 C6 C1 113.8(3) . . ? C5 C6 C1 120.6(4) . . ? O2 C7 C8 105.5(3) . . ? O2 C7 H7A 110.6 . . ? C8 C7 H7A 110.6 . . ? O2 C7 H7B 110.6 . . ? C8 C7 H7B 110.6 . . ? H7A C7 H7B 108.8 . . ? O3 C8 C7 108.4(3) . . ? O3 C8 H8A 110.0 . . ? C7 C8 H8A 110.0 . . ? O3 C8 H8B 110.0 . . ? C7 C8 H8B 110.0 . . ? H8A C8 H8B 108.4 . . ? O3 C9 C10 113.3(3) . . ? O3 C9 H9A 108.9 . . ? C10 C9 H9A 108.9 . . ? O3 C9 H9B 108.9 . . ? C10 C9 H9B 108.9 . . ? H9A C9 H9B 107.7 . . ? O4 C10 C9 108.3(3) . . ? O4 C10 H10A 110.0 . . ? C9 C10 H10A 110.0 . . ? O4 C10 H10B 110.0 . . ? C9 C10 H10B 110.0 . . ? H10A C10 H10B 108.4 . . ? O4 C11 C12 107.8(3) . . ? O4 C11 H11A 110.1 . . ? C12 C11 H11A 110.1 . . ? O4 C11 H11B 110.1 . . ? C12 C11 H11B 110.1 . . ? H11A C11 H11B 108.5 . . ? O5 C12 C11 111.7(3) . . ? O5 C12 H12A 109.3 . . ? C11 C12 H12A 109.3 . . ? O5 C12 H12B 109.3 . . ? C11 C12 H12B 109.3 . . ? H12A C12 H12B 107.9 . . ? O5 C13 C14 109.8(3) . . ? O5 C13 H13A 109.7 . . ? C14 C13 H13A 109.7 . . ? O5 C13 H13B 109.7 . . ? C14 C13 H13B 109.7 . . ? H13A C13 H13B 108.2 . . ? O1 C14 C13 106.3(3) . . ? O1 C14 H14A 110.5 . . ? C13 C14 H14A 110.5 . . ? O1 C14 H14B 110.5 . . ? C13 C14 H14B 110.5 . . ? H14A C14 H14B 108.7 . . ? C16 C15 O6 121.7(4) . . ? C16 C15 C20 120.2(4) . . ? O6 C15 C20 118.0(3) . . ? C15 C16 C17 120.4(5) . . ? C15 C16 H16 119.8 . . ? C17 C16 H16 119.8 . . ? C18 C17 C16 119.5(4) . . ? C18 C17 H17 120.2 . . ? C16 C17 H17 120.2 . . ? C17 C18 C19 121.2(4) . . ? C17 C18 H18 119.4 . . ? C19 C18 H18 119.4 . . ? C18 C19 C20 119.3(5) . . ? C18 C19 H19 120.3 . . ? C20 C19 H19 120.3 . . ? O7 C20 C19 125.0(4) . . ? O7 C20 C15 115.9(3) . . ? C19 C20 C15 119.1(4) . . ? O7 C21 C22 107.1(3) . . ? O7 C21 H21A 110.3 . . ? C22 C21 H21A 110.3 . . ? O7 C21 H21B 110.3 . . ? C22 C21 H21B 110.3 . . ? H21A C21 H21B 108.6 . . ? O8 C22 C21 108.8(3) . . ? O8 C22 H22A 109.9 . . ? C21 C22 H22A 109.9 . . ? O8 C22 H22B 109.9 . . ? C21 C22 H22B 109.9 . . ? H22A C22 H22B 108.3 . . ? O8 C23 C24 112.8(3) . . ? O8 C23 H23A 109.0 . . ? C24 C23 H23A 109.0 . . ? O8 C23 H23B 109.0 . . ? C24 C23 H23B 109.0 . . ? H23A C23 H23B 107.8 . . ? O9 C24 C23 108.1(3) . . ? O9 C24 H24A 110.1 . . ? C23 C24 H24A 110.1 . . ? O9 C24 H24B 110.1 . . ? C23 C24 H24B 110.1 . . ? H24A C24 H24B 108.4 . . ? O9 C25 C26 112.0(3) . . ? O9 C25 H25A 109.2 . . ? C26 C25 H25A 109.2 . . ? O9 C25 H25B 109.2 . . ? C26 C25 H25B 109.2 . . ? H25A C25 H25B 107.9 . . ? O10 C26 C25 107.7(3) . . ? O10 C26 H26A 110.2 . . ? C25 C26 H26A 110.2 . . ? O10 C26 H26B 110.2 . . ? C25 C26 H26B 110.2 . . ? H26A C26 H26B 108.5 . . ? O10 C27 C28 113.6(3) . . ? O10 C27 H27A 108.8 . . ? C28 C27 H27A 108.8 . . ? O10 C27 H27B 108.8 . . ? C28 C27 H27B 108.8 . . ? H27A C27 H27B 107.7 . . ? O6 C28 C27 106.9(3) . . ? O6 C28 H28A 110.3 . . ? C27 C28 H28A 110.3 . . ? O6 C28 H28B 110.3 . . ? C27 C28 H28B 110.3 . . ? H28A C28 H28B 108.6 . . ? C33 C29 C30 120.3(4) . . ? C33 C29 N1 119.9(4) . . ? C30 C29 N1 119.8(4) . . ? C31 C30 C29 119.5(5) . . ? C31 C30 H30 120.3 . . ? C29 C30 H30 120.3 . . ? C32 C31 C30 120.0(5) . . ? C32 C31 H31 120.0 . . ? C30 C31 H31 120.0 . . ? C31 C32 N2 119.5(4) . . ? C31 C32 H32 120.3 . . ? N2 C32 H32 120.3 . . ? N2 C33 C29 118.9(4) . . ? N2 C33 H33 120.5 . . ? C29 C33 H33 120.5 . . ? C38 C34 C35 120.2(3) . . ? C38 C34 N3 119.6(3) . . ? C35 C34 N3 120.1(3) . . ? C36 C35 C34 118.7(3) . . ? C36 C35 H35 120.6 . . ? C34 C35 H35 120.6 . . ? C37 C36 C35 119.7(3) . . ? C37 C36 H36 120.2 . . ? C35 C36 H36 120.2 . . ? N4 C37 C36 119.2(3) . . ? N4 C37 H37 120.4 . . ? C36 C37 H37 120.4 . . ? N4 C38 C34 118.8(3) . . ? N4 C38 H38 120.6 . . ? C34 C38 H38 120.6 . . ? O13 Cl1 O14 110.9(2) . . ? O13 Cl1 O12 110.12(17) . . ? O14 Cl1 O12 109.38(18) . . ? O13 Cl1 O11 109.30(16) . . ? O14 Cl1 O11 107.98(17) . . ? O12 Cl1 O11 109.10(16) . . ? O17A Cl2 O16A 114.4(3) . . ? O17A Cl2 O15 108.9(3) . . ? O16A Cl2 O15 109.5(2) . . ? O17A Cl2 O16B 45.0(7) . . ? O16A Cl2 O16B 123.0(6) . . ? O15 Cl2 O16B 127.1(6) . . ? O17A Cl2 O17B 130.9(8) . . ? O16A Cl2 O17B 36.4(8) . . ? O15 Cl2 O17B 117.9(7) . . ? O16B Cl2 O17B 108.4(11) . . ? O17A Cl2 O18A 109.4(3) . . ? O16A Cl2 O18A 109.4(3) . . ? O15 Cl2 O18A 104.8(2) . . ? O16B Cl2 O18A 65.0(8) . . ? O17B Cl2 O18A 73.1(9) . . ? O17A Cl2 O18B 58.5(5) . . ? O16A Cl2 O18B 63.1(5) . . ? O15 Cl2 O18B 101.6(5) . . ? O16B Cl2 O18B 96.7(9) . . ? O17B Cl2 O18B 96.8(10) . . ? O18A Cl2 O18B 153.4(5) . . ? O20B Cl3 O20A 115.6(11) . . ? O20B Cl3 O22 129.0(12) . . ? O20A Cl3 O22 114.3(2) . . ? O20B Cl3 O21A 39.4(16) . . ? O20A Cl3 O21A 111.4(2) . . ? O22 Cl3 O21A 110.7(3) . . ? O20B Cl3 O19A 68.7(18) . . ? O20A Cl3 O19A 108.7(3) . . ? O22 Cl3 O19A 104.2(3) . . ? O21A Cl3 O19A 107.1(4) . . ? O20B Cl3 O19B 116.8(18) . . ? O20A Cl3 O19B 51.2(10) . . ? O22 Cl3 O19B 87.3(7) . . ? O21A Cl3 O19B 83.4(9) . . ? O19A Cl3 O19B 159.9(11) . . ? O20B Cl3 O21B 109.3(17) . . ? O20A Cl3 O21B 46.6(7) . . ? O22 Cl3 O21B 111.8(6) . . ? O21A Cl3 O21B 137.4(6) . . ? O19A Cl3 O21B 64.3(7) . . ? O19B Cl3 O21B 96.3(14) . . ? O24 Cl4 O25 117.9(3) . . ? O24 Cl4 O26B 121.3(5) . . ? O25 Cl4 O26B 81.2(5) . . ? O24 Cl4 O23 117.0(3) . . ? O25 Cl4 O23 117.5(3) . . ? O26B Cl4 O23 94.4(4) . . ? O24 Cl4 O26A 84.5(4) . . ? O25 Cl4 O26A 113.4(4) . . ? O26B Cl4 O26A 40.1(4) . . ? O23 Cl4 O26A 99.2(4) . . ? C29 N1 H1NA 113(3) . . ? C29 N1 H1NB 100(3) . . ? H1NA N1 H1NB 110(4) . . ? C29 N1 H1NC 102(4) . . ? H1NA N1 H1NC 124(5) . . ? H1NB N1 H1NC 106(5) . . ? C33 N2 C32 121.9(5) . . ? C34 N3 H3NA 112(3) . . ? C34 N3 H3NB 111(2) . . ? H3NA N3 H3NB 107(3) . . ? C34 N3 H3NC 111(3) . . ? H3NA N3 H3NC 109(4) . . ? H3NB N3 H3NC 108(3) . . ? C37 N4 C38 123.4(3) . . ? C37 N4 H4N 122(3) . . ? C38 N4 H4N 114(3) . . ? C1 O1 C14 118.4(3) . . ? C6 O2 C7 118.9(3) . . ? C9 O3 C8 112.5(3) . . ? C11 O4 C10 112.6(3) . . ? C13 O5 C12 112.3(3) . . ? C15 O6 C28 114.7(3) . . ? C20 O7 C21 117.1(3) . . ? C22 O8 C23 112.9(3) . . ? C24 O9 C25 112.9(3) . . ? C26 O10 C27 113.9(3) . . ? Cl3 O19A O20B 48.5(8) . . ? Cl3 O19A O21B 61.4(7) . . ? O20B O19A O21B 93.7(11) . . ? O20A O19B Cl3 59.0(8) . . ? O21B O20A O19B 140.6(11) . . ? O21B O20A Cl3 74.9(9) . . ? O19B O20A Cl3 69.8(8) . . ? O21A O20B Cl3 83.0(16) . . ? O21A O20B O19A 143(2) . . ? Cl3 O20B O19A 62.8(15) . . ? O20B O21A Cl3 57.6(14) . . ? O20A O21B Cl3 58.5(9) . . ? O20A O21B O19A 110.5(14) . . ? Cl3 O21B O19A 54.3(6) . . ? O26B O26A Cl4 54.3(6) . . ? O17B O16A Cl2 74.3(10) . . ? O17B O16A O18B 133.0(12) . . ? Cl2 O16A O18B 65.1(5) . . ? O16B O17A Cl2 69.8(8) . . ? O16B O17A O18B 125.3(10) . . ? Cl2 O17A O18B 68.5(5) . . ? O16A O17B Cl2 69.2(11) . . ? O16A O17B O18A 123.0(13) . . ? Cl2 O17B O18A 53.9(6) . . ? Cl2 O18A O16B 56.7(6) . . ? Cl2 O18A O17B 53.1(7) . . ? O16B O18A O17B 90.5(9) . . ? O17A O16B Cl2 65.2(8) . . ? O17A O16B O18A 122.6(11) . . ? Cl2 O16B O18A 58.3(6) . . ? O17A O18B O16A 99.5(8) . . ? O17A O18B Cl2 53.0(5) . . ? O16A O18B Cl2 51.9(4) . . ? O26A O26B Cl4 85.6(7) . . ? 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 C32 H32 O22 0.95 2.23 3.128(6) 157.6 2 N1 H1NC O22 0.87(7) 2.28(7) 2.957(5) 134(6) . N1 H1NC O23 0.87(7) 2.12(7) 2.847(6) 140(6) . N1 H1NA O10 0.98(6) 1.80(6) 2.777(5) 178(5) 4_565 N1 H1NB O8 0.81(5) 2.20(5) 2.983(5) 161(4) 4_565 N3 H3NB O3 0.88(4) 2.13(4) 2.935(4) 153(3) 3_666 N3 H3NA O5 0.90(4) 1.89(4) 2.770(4) 166(4) 3_666 N3 H3NC O11 0.87(4) 2.08(4) 2.892(4) 155(4) 2_556 N4 H4N O27 0.86(4) 1.90(4) 2.702(4) 153(4) . C37 H37 O15 0.95 2.43 3.260(4) 146.1 2_546 C35 H35 O24 0.95 2.49 3.292(5) 141.8 4_666 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.252 _refine_diff_density_min -0.749 _refine_diff_density_rms 0.078 #END************************************************************** data_3AP-DB21C7 _database_code_depnum_ccdc_archive 'CCDC 846229' #TrackingRef '- Structures(3).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '3(C22 H28 O7),3(C5 H8 N2),6(Cl O4),5(H2 O)' _chemical_formula_sum 'C81 H118 Cl6 N6 O50' _chemical_formula_weight 2188.51 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.9802(8) _cell_length_b 12.7041(9) _cell_length_c 34.277(2) _cell_angle_alpha 85.190(1) _cell_angle_beta 89.215(1) _cell_angle_gamma 89.297(1) _cell_volume 5197.7(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6067 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 24.99 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.398 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2296 _exptl_absorpt_coefficient_mu 0.262 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9024 _exptl_absorpt_correction_T_max 0.9494 _exptl_absorpt_process_details Bruker-SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD 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 43314 _diffrn_reflns_av_R_equivalents 0.0345 _diffrn_reflns_av_sigmaI/netI 0.0490 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 1.19 _diffrn_reflns_theta_max 25.00 _reflns_number_total 18210 _reflns_number_gt 14548 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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. ; _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^)+(0.0683P)^2^+11.0448P] 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 18210 _refine_ls_number_parameters 1332 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0799 _refine_ls_R_factor_gt 0.0659 _refine_ls_wR_factor_ref 0.1668 _refine_ls_wR_factor_gt 0.1578 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.5206(3) 0.9414(3) 0.39495(11) 0.0300(8) Uani 1 1 d . . . C2 C 0.5510(4) 0.9047(4) 0.43203(13) 0.0470(11) Uani 1 1 d . . . H2 H 0.5406 0.8344 0.4411 0.056 Uiso 1 1 calc R . . C3 C 0.6121(5) 1.0789(5) 0.44108(16) 0.0755(18) Uani 1 1 d . . . H3 H 0.6438 1.1263 0.4568 0.091 Uiso 1 1 calc R . . N2 N 0.5813(3) 1.1116(3) 0.40514(11) 0.0490(9) Uani 1 1 d . . . C5 C 0.5359(3) 1.0454(3) 0.38190(12) 0.0365(9) Uani 1 1 d . . . H5 H 0.5145 1.0698 0.3567 0.044 Uiso 1 1 calc R . . C6 C 0.4298(3) 0.1756(2) 0.92317(10) 0.0207(7) Uani 1 1 d . . . C7 C 0.5424(3) 0.1651(3) 0.91784(10) 0.0233(7) Uani 1 1 d . . . H7 H 0.5836 0.2202 0.9056 0.028 Uiso 1 1 calc R . . C8 C 0.5362(3) -0.0071(3) 0.94824(10) 0.0256(8) Uani 1 1 d . . . H8 H 0.5740 -0.0690 0.9568 0.031 Uiso 1 1 calc R . . C9 C 0.4241(3) 0.0007(3) 0.95368(10) 0.0239(7) Uani 1 1 d . . . H9 H 0.3848 -0.0560 0.9658 0.029 Uiso 1 1 calc R . . C10 C 0.3681(3) 0.0935(3) 0.94117(10) 0.0241(7) Uani 1 1 d . . . H10 H 0.2914 0.1004 0.9448 0.029 Uiso 1 1 calc R . . C11 C 0.9736(3) 0.5119(2) 0.74396(9) 0.0190(7) Uani 1 1 d . . . C12 C 1.0245(3) 0.5222(3) 0.77879(10) 0.0225(7) Uani 1 1 d . . . H12 H 1.0833 0.5688 0.7802 0.027 Uiso 1 1 calc R . . C13 C 0.9064(3) 0.3940(3) 0.80995(11) 0.0284(8) Uani 1 1 d . . . H13 H 0.8853 0.3536 0.8327 0.034 Uiso 1 1 calc R . . C14 C 0.8538(3) 0.3822(3) 0.77526(10) 0.0248(7) Uani 1 1 d . . . H14 H 0.7964 0.3338 0.7743 0.030 Uiso 1 1 calc R . . C15 C 0.8867(3) 0.4426(3) 0.74176(10) 0.0224(7) Uani 1 1 d . . . H15 H 0.8508 0.4366 0.7182 0.027 Uiso 1 1 calc R . . C16 C 0.7912(3) 0.8524(3) 0.37358(11) 0.0307(8) Uani 1 1 d . . . C17 C 0.8816(3) 0.9110(3) 0.38214(12) 0.0374(9) Uani 1 1 d . . . H17 H 0.8996 0.9719 0.3664 0.045 Uiso 1 1 calc R . . C18 C 0.9462(4) 0.8790(4) 0.41440(13) 0.0437(11) Uani 1 1 d . . . H18 H 1.0065 0.9196 0.4207 0.052 Uiso 1 1 calc R . . C19 C 0.9216(4) 0.7881(4) 0.43702(12) 0.0466(11) Uani 1 1 d . . . H19 H 0.9663 0.7663 0.4582 0.056 Uiso 1 1 calc R . . C20 C 0.8302(3) 0.7281(4) 0.42856(12) 0.0429(10) Uani 1 1 d . . . H20 H 0.8137 0.6665 0.4441 0.052 Uiso 1 1 calc R . . C21 C 0.7639(3) 0.7605(3) 0.39691(11) 0.0347(9) Uani 1 1 d . . . C22 C 0.6404(4) 0.6141(3) 0.40742(14) 0.0477(11) Uani 1 1 d . . . H22A H 0.6420 0.6213 0.4354 0.057 Uiso 1 1 calc R . . H22B H 0.6926 0.5585 0.4014 0.057 Uiso 1 1 calc R . . C23 C 0.5253(4) 0.5882(3) 0.39528(14) 0.0476(11) Uani 1 1 d . . . H23A H 0.5216 0.5891 0.3670 0.057 Uiso 1 1 calc R . . H23B H 0.5044 0.5186 0.4066 0.057 Uiso 1 1 calc R . . C24 C 0.3393(3) 0.6337(3) 0.41420(13) 0.0417(10) Uani 1 1 d . . . H24A H 0.3372 0.5603 0.4247 0.050 Uiso 1 1 calc R . . H24B H 0.3017 0.6399 0.3892 0.050 Uiso 1 1 calc R . . C25 C 0.2828(4) 0.7015(4) 0.44163(12) 0.0436(11) Uani 1 1 d . . . H25A H 0.2074 0.6771 0.4471 0.052 Uiso 1 1 calc R . . H25B H 0.3229 0.6983 0.4661 0.052 Uiso 1 1 calc R . . C26 C 0.2363(3) 0.8820(4) 0.44630(12) 0.0439(11) Uani 1 1 d . . . C27 C 0.1943(4) 0.8626(5) 0.48423(13) 0.0591(14) Uani 1 1 d . . . H27 H 0.1957 0.7945 0.4965 0.071 Uiso 1 1 calc R . . C28 C 0.1509(5) 0.9442(7) 0.50326(17) 0.091(2) Uani 1 1 d . . . H28 H 0.1224 0.9309 0.5285 0.109 Uiso 1 1 calc R . . C29 C 0.1486(6) 1.0437(7) 0.48614(19) 0.101(3) Uani 1 1 d . . . H29 H 0.1191 1.0981 0.4998 0.121 Uiso 1 1 calc R . . C30 C 0.1899(5) 1.0657(6) 0.44836(17) 0.083(2) Uani 1 1 d . . . H30 H 0.1892 1.1344 0.4367 0.100 Uiso 1 1 calc R . . C31 C 0.2320(3) 0.9836(4) 0.42841(12) 0.0472(11) Uani 1 1 d . . . C32 C 0.2167(5) 1.0654(8) 0.36599(19) 0.127(4) Uani 1 1 d . . . H32A H 0.2356 1.1357 0.3727 0.152 Uiso 1 1 calc R . . H32B H 0.1371 1.0569 0.3705 0.152 Uiso 1 1 calc R . . C33 C 0.2395(3) 1.0595(3) 0.32439(13) 0.0406(10) Uani 1 1 d . . . H33A H 0.1999 1.0000 0.3155 0.049 Uiso 1 1 calc R . . H33B H 0.2113 1.1232 0.3101 0.049 Uiso 1 1 calc R . . C34 C 0.3834(4) 1.0486(4) 0.27724(12) 0.0467(11) Uani 1 1 d . . . H34A H 0.3587 1.1149 0.2639 0.056 Uiso 1 1 calc R . . H34B H 0.3437 0.9926 0.2660 0.056 Uiso 1 1 calc R . . C35 C 0.4961(5) 1.0359(9) 0.2691(2) 0.161(5) Uani 1 1 d . . . H35A H 0.5015 0.9978 0.2458 0.193 Uiso 1 1 calc R . . H35B H 0.5253 1.1059 0.2621 0.193 Uiso 1 1 calc R . . C36 C 0.6699(3) 0.9527(3) 0.28125(11) 0.0328(9) Uani 1 1 d . . . H36A H 0.6944 0.9978 0.2586 0.039 Uiso 1 1 calc R . . H36B H 0.6629 0.8814 0.2735 0.039 Uiso 1 1 calc R . . C37 C 0.7536(3) 0.9539(3) 0.31287(11) 0.0300(8) Uani 1 1 d . . . H37A H 0.8275 0.9375 0.3030 0.036 Uiso 1 1 calc R . . H37B H 0.7552 1.0229 0.3230 0.036 Uiso 1 1 calc R . . C38 C 0.3627(3) 0.0310(3) 0.84101(10) 0.0252(7) Uani 1 1 d . . . C39 C 0.4169(3) -0.0592(3) 0.83064(11) 0.0305(8) Uani 1 1 d . . . H39 H 0.4931 -0.0581 0.8251 0.037 Uiso 1 1 calc R . . C40 C 0.3573(3) -0.1512(3) 0.82858(10) 0.0297(8) Uani 1 1 d . . . H40 H 0.3930 -0.2115 0.8207 0.036 Uiso 1 1 calc R . . C41 C 0.2455(3) -0.1536(3) 0.83815(10) 0.0288(8) Uani 1 1 d . . . H41 H 0.2057 -0.2155 0.8366 0.035 Uiso 1 1 calc R . . C42 C 0.1918(3) -0.0646(3) 0.85011(10) 0.0267(8) Uani 1 1 d . . . H42 H 0.1165 -0.0670 0.8570 0.032 Uiso 1 1 calc R . . C43 C 0.2504(3) 0.0284(3) 0.85187(9) 0.0198(7) Uani 1 1 d . . . C44 C 0.0958(3) 0.1165(3) 0.88047(10) 0.0244(7) Uani 1 1 d . . . H44A H 0.0921 0.0609 0.9017 0.029 Uiso 1 1 calc R . . H44B H 0.0416 0.1018 0.8609 0.029 Uiso 1 1 calc R . . C45 C 0.0716(3) 0.2214(3) 0.89558(10) 0.0229(7) Uani 1 1 d . . . H45A H 0.0809 0.2773 0.8748 0.027 Uiso 1 1 calc R . . H45B H -0.0047 0.2240 0.9053 0.027 Uiso 1 1 calc R . . C46 C 0.1072(3) 0.3042(3) 0.95476(10) 0.0213(7) Uani 1 1 d . . . H46A H 0.0269 0.2980 0.9578 0.026 Uiso 1 1 calc R . . H46B H 0.1240 0.3769 0.9459 0.026 Uiso 1 1 calc R . . C47 C 0.1618(3) 0.2752(3) 0.99291(10) 0.0215(7) Uani 1 1 d . . . H47A H 0.1279 0.3143 1.0132 0.026 Uiso 1 1 calc R . . H47B H 0.1535 0.2003 1.0003 0.026 Uiso 1 1 calc R . . C48 C 0.3440(3) 0.2813(3) 1.02020(11) 0.0268(8) Uani 1 1 d . . . C49 C 0.3074(4) 0.2406(3) 1.05675(11) 0.0330(9) Uani 1 1 d . . . H49 H 0.2326 0.2242 1.0611 0.040 Uiso 1 1 calc R . . C50 C 0.3840(4) 0.2241(3) 1.08714(13) 0.0463(12) Uani 1 1 d . . . H50 H 0.3597 0.1979 1.1119 0.056 Uiso 1 1 calc R . . C51 C 0.4950(4) 0.2467(3) 1.08060(14) 0.0525(13) Uani 1 1 d . . . H51 H 0.5455 0.2342 1.1009 0.063 Uiso 1 1 calc R . . C52 C 0.5326(4) 0.2879(3) 1.04396(14) 0.0434(11) Uani 1 1 d . . . H52 H 0.6078 0.3023 1.0396 0.052 Uiso 1 1 calc R . . C53 C 0.4568(3) 0.3073(3) 1.01399(12) 0.0338(9) Uani 1 1 d . . . C54 C 0.5899(3) 0.4041(3) 0.97214(14) 0.0405(11) Uani 1 1 d . . . H54A H 0.6485 0.3508 0.9719 0.049 Uiso 1 1 calc R . . H54B H 0.6036 0.4477 0.9935 0.049 Uiso 1 1 calc R . . C55 C 0.5894(3) 0.4700(3) 0.93438(15) 0.0450(12) Uani 1 1 d . . . H55A H 0.5247 0.5167 0.9333 0.054 Uiso 1 1 calc R . . H55B H 0.6559 0.5131 0.9320 0.054 Uiso 1 1 calc R . . C56 C 0.5966(3) 0.4611(3) 0.86616(15) 0.0472(12) Uani 1 1 d . . . H56A H 0.6663 0.4994 0.8645 0.057 Uiso 1 1 calc R . . H56B H 0.5356 0.5118 0.8627 0.057 Uiso 1 1 calc R . . C57 C 0.5938(3) 0.3868(3) 0.83538(14) 0.0442(11) Uani 1 1 d . . . H57A H 0.6022 0.4249 0.8098 0.053 Uiso 1 1 calc R . . H57B H 0.6548 0.3360 0.8388 0.053 Uiso 1 1 calc R . . C58 C 0.4688(6) 0.2793(4) 0.80446(16) 0.081(2) Uani 1 1 d . . . H58A H 0.4055 0.3135 0.7911 0.098 Uiso 1 1 calc R . . H58B H 0.5327 0.2879 0.7869 0.098 Uiso 1 1 calc R . . C59 C 0.4484(10) 0.1805(5) 0.80998(18) 0.166(5) Uani 1 1 d . . . H59A H 0.5148 0.1455 0.8007 0.199 Uiso 1 1 calc R . . H59B H 0.3903 0.1683 0.7915 0.199 Uiso 1 1 calc R . . C60 C -0.0325(3) 0.7241(3) 0.29881(10) 0.0248(7) Uani 1 1 d . . . C61 C 0.0375(3) 0.8107(3) 0.29564(12) 0.0306(8) Uani 1 1 d . . . H61 H 0.0875 0.8207 0.3155 0.037 Uiso 1 1 calc R . . C62 C 0.0330(3) 0.8819(3) 0.26305(12) 0.0353(9) Uani 1 1 d . . . H62 H 0.0809 0.9392 0.2609 0.042 Uiso 1 1 calc R . . C63 C -0.0418(3) 0.8692(3) 0.23349(11) 0.0339(9) Uani 1 1 d . . . H63 H -0.0441 0.9174 0.2115 0.041 Uiso 1 1 calc R . . C64 C -0.1134(3) 0.7839(3) 0.23699(11) 0.0288(8) Uani 1 1 d . . . H64 H -0.1649 0.7754 0.2175 0.035 Uiso 1 1 calc R . . C65 C -0.1086(3) 0.7117(3) 0.26928(10) 0.0255(8) Uani 1 1 d . . . C66 C -0.2568(3) 0.6053(3) 0.29957(12) 0.0326(9) Uani 1 1 d . . . H66A H -0.3030 0.6681 0.3009 0.039 Uiso 1 1 calc R . . H66B H -0.2226 0.5883 0.3248 0.039 Uiso 1 1 calc R . . C67 C -0.3249(3) 0.5152(3) 0.28856(13) 0.0332(9) Uani 1 1 d . . . H67A H -0.3873 0.5040 0.3067 0.040 Uiso 1 1 calc R . . H67B H -0.3543 0.5309 0.2625 0.040 Uiso 1 1 calc R . . C68 C -0.3103(3) 0.3400(3) 0.27157(11) 0.0280(8) Uani 1 1 d . . . H68A H -0.3234 0.3623 0.2442 0.034 Uiso 1 1 calc R . . H68B H -0.3821 0.3261 0.2843 0.034 Uiso 1 1 calc R . . C69 C -0.2407(3) 0.2418(3) 0.27450(11) 0.0282(8) Uani 1 1 d . . . H69A H -0.2243 0.2212 0.3017 0.034 Uiso 1 1 calc R . . H69B H -0.2813 0.1848 0.2642 0.034 Uiso 1 1 calc R . . C70 C -0.0788(3) 0.1639(3) 0.24880(11) 0.0262(8) Uani 1 1 d . . . H70A H -0.1221 0.1172 0.2341 0.031 Uiso 1 1 calc R . . H70B H -0.0639 0.1283 0.2744 0.031 Uiso 1 1 calc R . . C71 C 0.0289(3) 0.1912(3) 0.22765(10) 0.0258(8) Uani 1 1 d . . . H71A H 0.0684 0.1275 0.2214 0.031 Uiso 1 1 calc R . . H71B H 0.0148 0.2344 0.2035 0.031 Uiso 1 1 calc R . . C72 C 0.1992(3) 0.2771(2) 0.24147(9) 0.0196(7) Uani 1 1 d . . . C73 C 0.2452(3) 0.2618(3) 0.20514(10) 0.0246(7) Uani 1 1 d . . . H73 H 0.2042 0.2295 0.1867 0.030 Uiso 1 1 calc R . . C74 C 0.3535(3) 0.2951(3) 0.19646(11) 0.0305(8) Uani 1 1 d . . . H74 H 0.3852 0.2847 0.1721 0.037 Uiso 1 1 calc R . . C75 C 0.4140(3) 0.3429(3) 0.22342(11) 0.0283(8) Uani 1 1 d . . . H75 H 0.4861 0.3656 0.2171 0.034 Uiso 1 1 calc R . . C76 C 0.3686(3) 0.3580(3) 0.26018(11) 0.0257(8) Uani 1 1 d . . . H76 H 0.4103 0.3902 0.2785 0.031 Uiso 1 1 calc R . . C77 C 0.2614(3) 0.3250(2) 0.26930(10) 0.0202(7) Uani 1 1 d . . . C78 C 0.2690(3) 0.3735(3) 0.33565(10) 0.0238(7) Uani 1 1 d . . . H78A H 0.3083 0.4376 0.3268 0.029 Uiso 1 1 calc R . . H78B H 0.3233 0.3206 0.3453 0.029 Uiso 1 1 calc R . . C79 C 0.1867(3) 0.3950(3) 0.36741(10) 0.0255(7) Uani 1 1 d . . . H79A H 0.1431 0.3325 0.3749 0.031 Uiso 1 1 calc R . . H79B H 0.2251 0.4152 0.3903 0.031 Uiso 1 1 calc R . . C80 C 0.0612(3) 0.5424(3) 0.37956(10) 0.0267(8) Uani 1 1 d . . . H80A H 0.1058 0.5441 0.4029 0.032 Uiso 1 1 calc R . . H80B H -0.0113 0.5135 0.3871 0.032 Uiso 1 1 calc R . . C81 C 0.0488(3) 0.6507(3) 0.35937(10) 0.0278(8) Uani 1 1 d . . . H81A H 0.0203 0.6995 0.3775 0.033 Uiso 1 1 calc R . . H81B H 0.1204 0.6760 0.3491 0.033 Uiso 1 1 calc R . . Cl1 Cl 0.16198(7) 0.91025(6) 0.00906(2) 0.02518(19) Uani 1 1 d . . . Cl2 Cl 0.20999(7) 0.94816(7) 0.14995(3) 0.0285(2) Uani 1 1 d . . . Cl3 Cl 0.37156(7) 0.72099(7) 0.29585(3) 0.0329(2) Uani 1 1 d . . . Cl4 Cl 0.09748(11) 0.76153(12) 0.62281(4) 0.0761(5) Uani 1 1 d . . . Cl5 Cl 0.27058(6) 0.50905(6) 0.84638(2) 0.02211(18) Uani 1 1 d . . . Cl6 Cl 0.90732(7) 0.49703(6) 0.91101(2) 0.02536(19) Uani 1 1 d . . . H4N H 0.673(4) 0.063(4) 0.9266(13) 0.051(13) Uiso 1 1 d . . . H6N H 1.018(3) 0.471(3) 0.8325(12) 0.023(10) Uiso 1 1 d . . . H1NA H 0.516(5) 0.873(4) 0.3511(16) 0.058(17) Uiso 1 1 d . . . H3NA H 0.297(4) 0.262(3) 0.9088(11) 0.030(10) Uiso 1 1 d . . . H5NA H 0.977(3) 0.557(3) 0.6855(13) 0.038(11) Uiso 1 1 d . . . H1NB H 0.405(6) 0.891(5) 0.3632(18) 0.09(2) Uiso 1 1 d . . . H3NB H 0.390(4) 0.327(4) 0.9265(16) 0.068(16) Uiso 1 1 d . . . H5NB H 1.088(4) 0.569(3) 0.7061(11) 0.027(10) Uiso 1 1 d . . . H1NC H 0.462(4) 0.796(5) 0.3792(16) 0.076(17) Uiso 1 1 d . . . H3NC H 0.407(4) 0.305(4) 0.8844(16) 0.062(15) Uiso 1 1 d . . . H5NC H 1.001(4) 0.650(4) 0.7100(13) 0.050(13) Uiso 1 1 d . . . N1 N 0.4722(3) 0.8728(3) 0.36872(11) 0.0317(7) Uani 1 1 d . . . C4 C 0.5975(6) 0.9750(5) 0.45555(15) 0.0783(19) Uani 1 1 d . . . H4 H 0.6188 0.9526 0.4809 0.094 Uiso 1 1 calc R . . N3 N 0.3756(2) 0.2743(2) 0.90903(10) 0.0243(6) Uani 1 1 d . . . N4 N 0.5922(2) 0.0743(2) 0.93055(9) 0.0252(6) Uani 1 1 d . . . N5 N 1.0148(3) 0.5754(2) 0.70939(8) 0.0205(6) Uani 1 1 d . . . N6 N 0.9887(2) 0.4646(2) 0.81073(9) 0.0257(7) Uani 1 1 d . . . O1 O 0.7195(2) 0.8756(2) 0.34281(7) 0.0316(6) Uani 1 1 d . . . O2 O 0.6696(2) 0.7110(2) 0.38613(8) 0.0395(7) Uani 1 1 d . . . O3 O 0.4520(2) 0.6671(2) 0.40920(8) 0.0404(7) Uani 1 1 d . . . O4 O 0.2804(2) 0.8071(2) 0.42407(7) 0.0378(6) Uani 1 1 d . . . O5 O 0.2689(3) 0.9968(3) 0.38997(8) 0.0508(8) Uani 1 1 d . . . O6 O 0.3516(3) 1.0484(4) 0.31612(10) 0.0994(18) Uani 1 1 d . . . O7 O 0.5653(2) 0.9889(3) 0.29471(8) 0.0484(8) Uani 1 1 d . . . O8 O 0.4189(2) 0.1238(2) 0.84291(8) 0.0365(7) Uani 1 1 d . . . O9 O 0.20619(18) 0.12109(17) 0.86348(7) 0.0227(5) Uani 1 1 d . . . O10 O 0.14757(17) 0.23506(17) 0.92643(6) 0.0204(5) Uani 1 1 d . . . O11 O 0.27811(19) 0.30103(18) 0.98815(7) 0.0242(5) Uani 1 1 d . . . O12 O 0.4825(2) 0.35444(19) 0.97742(8) 0.0331(6) Uani 1 1 d . . . O13 O 0.5866(2) 0.40308(19) 0.90342(9) 0.0365(7) Uani 1 1 d . . . O14 O 0.4905(2) 0.3338(2) 0.83797(9) 0.0458(8) Uani 1 1 d . . . O15 O -0.02836(19) 0.64302(18) 0.32794(7) 0.0261(5) Uani 1 1 d . . . O16 O -0.17249(19) 0.62176(19) 0.26932(7) 0.0290(6) Uani 1 1 d . . . O17 O -0.25581(18) 0.42227(18) 0.28964(7) 0.0262(5) Uani 1 1 d . . . O18 O -0.13885(19) 0.25958(18) 0.25283(7) 0.0251(5) Uani 1 1 d . . . O19 O 0.09318(18) 0.24806(18) 0.25352(6) 0.0220(5) Uani 1 1 d . . . O20 O 0.20732(18) 0.33639(18) 0.30431(6) 0.0221(5) Uani 1 1 d . . . O21 O 0.1157(2) 0.47960(18) 0.35183(7) 0.0257(5) Uani 1 1 d . . . O22 O 0.2182(2) 1.00290(19) 0.01954(7) 0.0293(6) Uani 1 1 d . . . O23 O 0.2271(2) 0.8185(2) 0.02321(9) 0.0414(7) Uani 1 1 d . . . O24 O 0.0532(2) 0.9049(2) 0.02646(8) 0.0382(7) Uani 1 1 d . . . O25 O 0.1541(2) 0.9142(2) -0.03275(8) 0.0424(7) Uani 1 1 d . . . O26 O 0.1969(2) 0.9498(2) 0.10748(8) 0.0416(7) Uani 1 1 d . . . O27 O 0.3163(2) 0.9855(3) 0.15759(11) 0.0648(10) Uani 1 1 d . . . O28 O 0.1977(3) 0.8421(2) 0.16578(9) 0.0551(9) Uani 1 1 d . . . O29 O 0.1245(2) 1.0129(2) 0.16476(8) 0.0376(6) Uani 1 1 d . . . O30 O 0.4880(2) 0.7408(2) 0.30001(8) 0.0399(7) Uani 1 1 d . . . O31 O 0.3115(2) 0.7669(4) 0.32672(9) 0.0677(11) Uani 1 1 d . . . O32 O 0.3527(4) 0.6118(3) 0.29765(14) 0.0933(15) Uani 1 1 d . . . O33 O 0.3330(2) 0.7682(2) 0.25939(8) 0.0417(7) Uani 1 1 d . . . O34 O 0.1899(3) 0.8291(3) 0.61932(12) 0.0657(10) Uani 1 1 d . . . O35 O 0.0319(3) 0.7794(5) 0.65623(13) 0.123(2) Uani 1 1 d . . . O36 O 0.1376(5) 0.6556(3) 0.62747(16) 0.131(2) Uani 1 1 d . . . O37 O 0.0314(4) 0.7779(6) 0.58864(13) 0.136(3) Uani 1 1 d . . . O38 O 0.2329(2) 0.40601(19) 0.84015(8) 0.0346(6) Uani 1 1 d . . . O39 O 0.3058(2) 0.5101(2) 0.88664(7) 0.0364(6) Uani 1 1 d . . . O40 O 0.3612(2) 0.5386(2) 0.82076(8) 0.0396(7) Uani 1 1 d . . . O41 O 0.17991(19) 0.58433(18) 0.83997(7) 0.0263(5) Uani 1 1 d . . . O42 O 0.8441(2) 0.4038(2) 0.91010(9) 0.0381(6) Uani 1 1 d . . . O43 O 0.9246(3) 0.5216(2) 0.95038(8) 0.0460(7) Uani 1 1 d . . . O44 O 1.0150(2) 0.4811(2) 0.89305(8) 0.0363(6) Uani 1 1 d . . . O45 O 0.8520(2) 0.5842(2) 0.88909(9) 0.0403(7) Uani 1 1 d . . . O46 O 0.0161(2) 0.74082(19) 0.88361(7) 0.0301(6) Uani 1 1 d . . . O47 O 0.1808(2) 0.6685(2) 0.91847(7) 0.0311(6) Uani 1 1 d . . . O48 O 0.1464(2) 0.6376(2) 0.99168(8) 0.0382(6) Uani 1 1 d . . . O49 O 0.6029(4) 0.3136(3) 0.37275(13) 0.0866(13) Uani 1 1 d . . . O50 O 0.9516(2) 0.8898(2) 0.92571(8) 0.0323(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 C1 0.0199(18) 0.037(2) 0.033(2) 0.0022(16) 0.0040(15) -0.0016(15) C2 0.053(3) 0.050(3) 0.037(2) 0.005(2) -0.005(2) -0.010(2) C3 0.103(5) 0.076(4) 0.049(3) -0.009(3) -0.017(3) -0.044(3) N2 0.049(2) 0.057(2) 0.041(2) -0.0020(18) -0.0079(17) -0.0161(19) C5 0.031(2) 0.040(2) 0.039(2) -0.0011(18) -0.0035(17) -0.0038(17) C6 0.0212(17) 0.0171(16) 0.0244(17) -0.0052(13) -0.0036(13) 0.0045(13) C7 0.0220(17) 0.0217(17) 0.0266(18) -0.0040(14) -0.0003(14) -0.0001(13) C8 0.0307(19) 0.0198(18) 0.0260(18) -0.0014(14) 0.0000(15) 0.0063(14) C9 0.0278(19) 0.0191(17) 0.0248(18) -0.0027(14) 0.0006(14) 0.0015(14) C10 0.0204(17) 0.0269(19) 0.0254(18) -0.0044(14) 0.0013(14) 0.0013(14) C11 0.0170(16) 0.0199(17) 0.0199(16) -0.0016(13) 0.0015(13) 0.0043(13) C12 0.0189(17) 0.0203(17) 0.0281(18) -0.0005(14) 0.0005(14) 0.0018(13) C13 0.0247(18) 0.031(2) 0.0278(19) 0.0040(15) 0.0068(15) 0.0042(15) C14 0.0153(16) 0.0230(18) 0.036(2) -0.0018(15) 0.0045(14) -0.0002(13) C15 0.0187(17) 0.0214(17) 0.0276(18) -0.0057(14) -0.0011(14) 0.0036(13) C16 0.0275(19) 0.037(2) 0.0279(19) -0.0063(16) 0.0026(15) 0.0053(16) C17 0.039(2) 0.033(2) 0.042(2) -0.0112(18) 0.0025(18) 0.0027(17) C18 0.036(2) 0.050(3) 0.049(3) -0.029(2) -0.007(2) 0.0055(19) C19 0.045(3) 0.066(3) 0.030(2) -0.015(2) -0.0037(19) 0.021(2) C20 0.037(2) 0.060(3) 0.031(2) 0.000(2) 0.0016(18) 0.009(2) C21 0.030(2) 0.044(2) 0.029(2) -0.0013(17) 0.0038(16) 0.0033(17) C22 0.048(3) 0.042(3) 0.048(3) 0.021(2) 0.002(2) 0.002(2) C23 0.059(3) 0.028(2) 0.053(3) 0.0134(19) 0.004(2) -0.007(2) C24 0.041(2) 0.039(2) 0.042(2) 0.0149(19) -0.0113(19) -0.0154(19) C25 0.043(2) 0.056(3) 0.030(2) 0.0101(19) -0.0031(18) -0.018(2) C26 0.023(2) 0.076(3) 0.034(2) -0.014(2) -0.0024(17) 0.005(2) C27 0.034(2) 0.114(5) 0.030(2) -0.014(3) 0.0034(19) 0.001(3) C28 0.062(4) 0.173(8) 0.040(3) -0.033(4) 0.005(3) 0.035(4) C29 0.106(5) 0.151(7) 0.049(4) -0.042(4) 0.002(3) 0.064(5) C30 0.096(5) 0.098(5) 0.060(4) -0.034(3) -0.009(3) 0.052(4) C31 0.034(2) 0.076(3) 0.034(2) -0.020(2) -0.0024(18) 0.016(2) C32 0.048(3) 0.238(10) 0.077(4) 0.072(6) 0.024(3) 0.055(5) C33 0.033(2) 0.033(2) 0.055(3) 0.0094(19) -0.0106(19) 0.0020(17) C34 0.057(3) 0.045(3) 0.038(2) 0.0003(19) -0.012(2) 0.017(2) C35 0.060(4) 0.318(13) 0.077(5) 0.125(7) 0.036(3) 0.072(6) C36 0.040(2) 0.027(2) 0.030(2) 0.0023(16) 0.0093(17) -0.0012(16) C37 0.032(2) 0.0233(19) 0.035(2) 0.0010(15) 0.0043(16) -0.0049(15) C38 0.0254(18) 0.0259(19) 0.0252(18) -0.0069(14) -0.0029(14) -0.0024(14) C39 0.0231(18) 0.040(2) 0.030(2) -0.0127(16) -0.0015(15) 0.0033(16) C40 0.042(2) 0.0229(19) 0.0252(19) -0.0075(15) -0.0079(16) 0.0103(16) C41 0.043(2) 0.0167(17) 0.0264(19) -0.0010(14) -0.0024(16) -0.0044(15) C42 0.0293(19) 0.0256(19) 0.0251(18) -0.0005(14) 0.0027(15) -0.0057(15) C43 0.0230(17) 0.0201(17) 0.0165(16) -0.0022(13) -0.0013(13) -0.0013(13) C44 0.0180(17) 0.0278(19) 0.0279(18) -0.0050(15) 0.0001(14) -0.0037(14) C45 0.0173(16) 0.0281(18) 0.0234(17) -0.0026(14) -0.0011(13) 0.0020(13) C46 0.0157(16) 0.0194(17) 0.0293(18) -0.0046(14) 0.0020(13) 0.0021(13) C47 0.0213(17) 0.0200(17) 0.0235(17) -0.0046(13) 0.0031(13) 0.0003(13) C48 0.034(2) 0.0159(17) 0.033(2) -0.0103(14) -0.0154(16) 0.0092(14) C49 0.048(2) 0.0225(19) 0.029(2) -0.0087(15) -0.0104(17) 0.0086(16) C50 0.076(3) 0.032(2) 0.033(2) -0.0137(18) -0.023(2) 0.014(2) C51 0.074(3) 0.030(2) 0.057(3) -0.016(2) -0.048(3) 0.018(2) C52 0.046(2) 0.021(2) 0.066(3) -0.016(2) -0.034(2) 0.0116(17) C53 0.037(2) 0.0168(18) 0.049(2) -0.0112(17) -0.0193(18) 0.0062(15) C54 0.0181(18) 0.027(2) 0.079(3) -0.024(2) -0.0108(19) 0.0027(15) C55 0.0212(19) 0.020(2) 0.095(4) -0.011(2) 0.007(2) -0.0037(15) C56 0.0207(19) 0.028(2) 0.089(4) 0.020(2) -0.009(2) -0.0058(16) C57 0.024(2) 0.035(2) 0.069(3) 0.018(2) 0.018(2) 0.0051(17) C58 0.141(6) 0.048(3) 0.058(3) -0.029(3) 0.061(4) -0.030(3) C59 0.377(15) 0.066(4) 0.053(4) 0.034(3) -0.103(6) -0.132(7) C60 0.0225(17) 0.0201(17) 0.0318(19) -0.0038(14) 0.0061(15) 0.0043(14) C61 0.0270(19) 0.0246(19) 0.041(2) -0.0041(16) -0.0002(16) 0.0021(15) C62 0.035(2) 0.0229(19) 0.047(2) -0.0011(17) 0.0072(18) -0.0047(16) C63 0.038(2) 0.030(2) 0.032(2) 0.0014(16) 0.0081(17) 0.0036(17) C64 0.0245(18) 0.033(2) 0.0299(19) -0.0072(16) 0.0030(15) 0.0047(15) C65 0.0213(17) 0.0226(18) 0.033(2) -0.0059(15) 0.0075(15) 0.0025(14) C66 0.0222(18) 0.030(2) 0.046(2) -0.0074(17) 0.0092(16) 0.0024(15) C67 0.0191(18) 0.028(2) 0.052(2) -0.0017(17) 0.0051(16) 0.0054(15) C68 0.0217(18) 0.0251(19) 0.037(2) 0.0017(15) -0.0039(15) -0.0051(14) C69 0.0216(18) 0.0238(18) 0.039(2) -0.0002(15) -0.0001(15) -0.0050(14) C70 0.0248(18) 0.0185(17) 0.036(2) -0.0056(15) -0.0019(15) -0.0007(14) C71 0.0273(19) 0.0240(18) 0.0272(18) -0.0076(14) -0.0049(15) -0.0006(14) C72 0.0203(17) 0.0139(16) 0.0239(17) 0.0009(13) 0.0000(13) 0.0022(12) C73 0.0264(18) 0.0242(18) 0.0231(18) -0.0015(14) -0.0016(14) 0.0008(14) C74 0.0287(19) 0.036(2) 0.0255(19) 0.0002(16) 0.0060(15) 0.0025(16) C75 0.0206(18) 0.031(2) 0.032(2) 0.0031(16) 0.0041(15) -0.0023(15) C76 0.0208(17) 0.0226(18) 0.034(2) -0.0015(15) -0.0029(15) 0.0009(14) C77 0.0195(16) 0.0164(16) 0.0241(17) 0.0007(13) 0.0001(13) 0.0044(13) C78 0.0198(17) 0.0246(18) 0.0276(18) -0.0040(14) -0.0085(14) 0.0005(14) C79 0.0278(18) 0.0257(18) 0.0230(18) -0.0017(14) -0.0072(14) 0.0024(14) C80 0.0262(18) 0.032(2) 0.0229(18) -0.0087(15) 0.0022(14) 0.0027(15) C81 0.0254(18) 0.031(2) 0.0288(19) -0.0117(15) 0.0007(15) 0.0017(15) Cl1 0.0218(4) 0.0243(4) 0.0293(4) -0.0008(3) -0.0040(3) 0.0016(3) Cl2 0.0212(4) 0.0328(5) 0.0308(5) 0.0009(4) 0.0027(3) 0.0017(3) Cl3 0.0295(5) 0.0361(5) 0.0324(5) 0.0023(4) -0.0008(4) -0.0110(4) Cl4 0.0601(8) 0.0934(11) 0.0671(9) 0.0489(8) -0.0279(7) -0.0396(7) Cl5 0.0173(4) 0.0236(4) 0.0247(4) 0.0021(3) -0.0004(3) 0.0000(3) Cl6 0.0225(4) 0.0229(4) 0.0304(5) -0.0008(3) 0.0002(3) -0.0011(3) N1 0.0290(19) 0.0305(19) 0.0351(19) 0.0000(15) -0.0012(16) 0.0008(14) C4 0.112(5) 0.090(4) 0.031(3) 0.011(3) -0.021(3) -0.037(4) N3 0.0160(15) 0.0181(15) 0.0384(18) 0.0002(13) 0.0015(13) 0.0014(11) N4 0.0197(15) 0.0254(16) 0.0311(16) -0.0062(13) -0.0023(12) 0.0057(12) N5 0.0180(16) 0.0235(16) 0.0200(15) -0.0012(12) -0.0013(12) 0.0002(12) N6 0.0258(16) 0.0306(17) 0.0207(16) -0.0026(13) -0.0043(13) 0.0024(13) O1 0.0309(14) 0.0306(14) 0.0317(14) 0.0065(11) 0.0021(11) -0.0039(11) O2 0.0373(15) 0.0407(16) 0.0376(16) 0.0158(13) -0.0028(12) -0.0072(12) O3 0.0408(16) 0.0334(15) 0.0448(17) 0.0116(13) -0.0049(13) -0.0091(12) O4 0.0381(15) 0.0481(17) 0.0269(14) -0.0013(12) 0.0022(12) -0.0059(13) O5 0.0509(18) 0.067(2) 0.0347(16) -0.0085(14) -0.0030(14) 0.0325(16) O6 0.0367(19) 0.202(5) 0.047(2) 0.057(3) 0.0098(16) 0.027(2) O7 0.0415(17) 0.063(2) 0.0398(17) 0.0005(15) -0.0018(13) 0.0175(15) O8 0.0350(15) 0.0394(16) 0.0380(15) -0.0197(12) 0.0156(12) -0.0196(12) O9 0.0224(12) 0.0181(12) 0.0276(13) -0.0019(9) 0.0048(10) -0.0020(9) O10 0.0157(11) 0.0247(12) 0.0212(12) -0.0040(9) 0.0004(9) 0.0038(9) O11 0.0225(12) 0.0236(12) 0.0266(13) -0.0022(10) -0.0063(10) 0.0025(10) O12 0.0236(13) 0.0240(13) 0.0523(17) -0.0051(12) -0.0118(12) -0.0017(10) O13 0.0238(13) 0.0158(13) 0.069(2) -0.0011(12) -0.0018(13) -0.0013(10) O14 0.0486(17) 0.0288(15) 0.062(2) -0.0201(13) 0.0333(15) -0.0156(13) O15 0.0239(12) 0.0221(12) 0.0321(13) -0.0012(10) -0.0014(10) 0.0002(10) O16 0.0239(13) 0.0251(13) 0.0386(15) -0.0069(11) 0.0049(11) 0.0004(10) O17 0.0189(12) 0.0229(13) 0.0371(14) -0.0032(10) -0.0041(10) 0.0022(9) O18 0.0215(12) 0.0215(12) 0.0319(13) -0.0007(10) 0.0016(10) -0.0014(9) O19 0.0198(12) 0.0236(12) 0.0232(12) -0.0052(10) -0.0001(9) -0.0026(9) O20 0.0202(12) 0.0247(12) 0.0216(12) -0.0037(9) -0.0013(9) -0.0006(9) O21 0.0309(13) 0.0265(13) 0.0203(12) -0.0054(10) -0.0041(10) 0.0064(10) O22 0.0272(13) 0.0240(13) 0.0364(14) -0.0008(11) -0.0026(11) -0.0004(10) O23 0.0442(16) 0.0232(14) 0.0578(19) -0.0068(13) -0.0217(14) 0.0095(12) O24 0.0254(14) 0.0355(15) 0.0522(17) 0.0040(13) 0.0032(12) -0.0029(11) O25 0.0379(16) 0.0563(19) 0.0335(15) -0.0068(13) -0.0070(12) 0.0008(13) O26 0.0342(15) 0.0587(19) 0.0303(15) 0.0014(13) 0.0049(12) 0.0178(13) O27 0.0278(16) 0.092(3) 0.075(2) -0.003(2) -0.0102(16) -0.0133(16) O28 0.077(2) 0.0334(17) 0.0520(19) 0.0087(14) 0.0074(17) 0.0064(15) O29 0.0336(15) 0.0443(16) 0.0366(15) -0.0154(12) 0.0033(12) 0.0050(12) O30 0.0269(14) 0.0434(17) 0.0503(17) -0.0102(13) -0.0024(12) 0.0010(12) O31 0.0313(16) 0.142(4) 0.0333(17) -0.0258(19) 0.0074(13) -0.0187(19) O32 0.109(3) 0.040(2) 0.128(4) 0.022(2) -0.057(3) -0.036(2) O33 0.0446(17) 0.0519(18) 0.0279(14) 0.0017(13) -0.0057(12) -0.0003(14) O34 0.0483(19) 0.0418(19) 0.104(3) 0.0105(18) 0.0241(19) -0.0092(15) O35 0.052(2) 0.232(6) 0.070(3) 0.074(4) 0.001(2) -0.036(3) O36 0.207(6) 0.055(3) 0.125(4) 0.044(3) -0.092(4) -0.068(3) O37 0.079(3) 0.248(7) 0.067(3) 0.082(4) -0.031(2) -0.036(4) O38 0.0309(14) 0.0212(13) 0.0517(17) -0.0049(12) 0.0054(12) 0.0014(11) O39 0.0321(14) 0.0463(16) 0.0301(14) 0.0004(12) -0.0050(11) 0.0128(12) O40 0.0269(14) 0.0510(17) 0.0381(16) 0.0119(13) 0.0059(12) -0.0050(12) O41 0.0248(13) 0.0223(12) 0.0319(13) -0.0014(10) -0.0093(10) 0.0038(10) O42 0.0321(14) 0.0250(14) 0.0581(18) -0.0073(12) -0.0019(13) -0.0042(11) O43 0.071(2) 0.0309(15) 0.0377(16) -0.0099(12) 0.0082(15) -0.0046(14) O44 0.0267(14) 0.0446(16) 0.0356(15) 0.0092(12) -0.0003(11) 0.0025(12) O45 0.0307(14) 0.0280(14) 0.0608(19) 0.0058(13) -0.0108(13) 0.0029(11) O46 0.0340(14) 0.0259(13) 0.0297(14) 0.0011(10) 0.0023(11) 0.0010(11) O47 0.0306(14) 0.0328(14) 0.0303(14) -0.0049(11) -0.0010(11) 0.0000(11) O48 0.0456(16) 0.0411(16) 0.0284(14) -0.0048(12) -0.0019(12) -0.0072(13) O49 0.091(3) 0.058(2) 0.103(3) 0.027(2) 0.023(2) 0.028(2) O50 0.0313(14) 0.0301(14) 0.0358(15) -0.0061(11) -0.0022(11) 0.0031(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.369(6) . ? C1 C5 1.373(5) . ? C1 N1 1.435(5) . ? C2 C4 1.379(7) . ? C2 H2 0.9300 . ? C3 N2 1.323(6) . ? C3 C4 1.383(8) . ? C3 H3 0.9300 . ? N2 C5 1.332(5) . ? C5 H5 0.9300 . ? C6 C7 1.365(5) . ? C6 C10 1.383(5) . ? C6 N3 1.455(4) . ? C7 N4 1.335(4) . ? C7 H7 0.9300 . ? C8 N4 1.337(5) . ? C8 C9 1.357(5) . ? C8 H8 0.9300 . ? C9 C10 1.389(5) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.365(5) . ? C11 C15 1.379(5) . ? C11 N5 1.460(4) . ? C12 N6 1.334(4) . ? C12 H12 0.9300 . ? C13 N6 1.343(5) . ? C13 C14 1.374(5) . ? C13 H13 0.9300 . ? C14 C15 1.382(5) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.372(6) . ? C16 O1 1.379(4) . ? C16 C21 1.398(5) . ? C17 C18 1.388(6) . ? C17 H17 0.9300 . ? C18 C19 1.369(7) . ? C18 H18 0.9300 . ? C19 C20 1.389(6) . ? C19 H19 0.9300 . ? C20 C21 1.385(6) . ? C20 H20 0.9300 . ? C21 O2 1.370(5) . ? C22 O2 1.423(5) . ? C22 C23 1.495(6) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 O3 1.432(5) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 O3 1.424(5) . ? C24 C25 1.479(6) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 O4 1.424(5) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 O4 1.365(5) . ? C26 C31 1.383(7) . ? C26 C27 1.391(6) . ? C27 C28 1.364(8) . ? C27 H27 0.9300 . ? C28 C29 1.349(10) . ? C28 H28 0.9300 . ? C29 C30 1.388(9) . ? C29 H29 0.9300 . ? C30 C31 1.380(7) . ? C30 H30 0.9300 . ? C31 O5 1.382(5) . ? C32 O5 1.306(7) . ? C32 C33 1.456(8) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 O6 1.377(5) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C34 O6 1.381(5) . ? C34 C35 1.385(7) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C35 O7 1.316(6) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 O7 1.415(5) . ? C36 C37 1.488(5) . ? C36 H36A 0.9700 . ? C36 H36B 0.9700 . ? C37 O1 1.427(4) . ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? C38 O8 1.371(4) . ? C38 C39 1.380(5) . ? C38 C43 1.390(5) . ? C39 C40 1.385(5) . ? C39 H39 0.9300 . ? C40 C41 1.375(5) . ? C40 H40 0.9300 . ? C41 C42 1.383(5) . ? C41 H41 0.9300 . ? C42 C43 1.388(5) . ? C42 H42 0.9300 . ? C43 O9 1.372(4) . ? C44 O9 1.438(4) . ? C44 C45 1.494(5) . ? C44 H44A 0.9700 . ? C44 H44B 0.9700 . ? C45 O10 1.427(4) . ? C45 H45A 0.9700 . ? C45 H45B 0.9700 . ? C46 O10 1.438(4) . ? C46 C47 1.487(5) . ? C46 H46A 0.9700 . ? C46 H46B 0.9700 . ? C47 O11 1.439(4) . ? C47 H47A 0.9700 . ? C47 H47B 0.9700 . ? C48 O11 1.366(4) . ? C48 C49 1.383(5) . ? C48 C53 1.404(5) . ? C49 C50 1.398(6) . ? C49 H49 0.9300 . ? C50 C51 1.375(7) . ? C50 H50 0.9300 . ? C51 C52 1.391(7) . ? C51 H51 0.9300 . ? C52 C53 1.384(5) . ? C52 H52 0.9300 . ? C53 O12 1.376(5) . ? C54 O12 1.442(4) . ? C54 C55 1.482(6) . ? C54 H54A 0.9700 . ? C54 H54B 0.9700 . ? C55 O13 1.415(5) . ? C55 H55A 0.9700 . ? C55 H55B 0.9700 . ? C56 O13 1.424(5) . ? C56 C57 1.475(7) . ? C56 H56A 0.9700 . ? C56 H56B 0.9700 . ? C57 O14 1.414(5) . ? C57 H57A 0.9700 . ? C57 H57B 0.9700 . ? C58 C59 1.279(7) . ? C58 O14 1.419(6) . ? C58 H58A 0.9700 . ? C58 H58B 0.9700 . ? C59 O8 1.333(6) . ? C59 H59A 0.9700 . ? C59 H59B 0.9700 . ? C60 O15 1.374(4) . ? C60 C61 1.388(5) . ? C60 C65 1.392(5) . ? C61 C62 1.378(5) . ? C61 H61 0.9300 . ? C62 C63 1.383(6) . ? C62 H62 0.9300 . ? C63 C64 1.387(5) . ? C63 H63 0.9300 . ? C64 C65 1.378(5) . ? C64 H64 0.9300 . ? C65 O16 1.383(4) . ? C66 O16 1.442(4) . ? C66 C67 1.490(5) . ? C66 H66A 0.9700 . ? C66 H66B 0.9700 . ? C67 O17 1.432(4) . ? C67 H67A 0.9700 . ? C67 H67B 0.9700 . ? C68 O17 1.428(4) . ? C68 C69 1.490(5) . ? C68 H68A 0.9700 . ? C68 H68B 0.9700 . ? C69 O18 1.431(4) . ? C69 H69A 0.9700 . ? C69 H69B 0.9700 . ? C70 O18 1.421(4) . ? C70 C71 1.502(5) . ? C70 H70A 0.9700 . ? C70 H70B 0.9700 . ? C71 O19 1.429(4) . ? C71 H71A 0.9700 . ? C71 H71B 0.9700 . ? C72 O19 1.375(4) . ? C72 C73 1.383(5) . ? C72 C77 1.401(5) . ? C73 C74 1.390(5) . ? C73 H73 0.9300 . ? C74 C75 1.368(5) . ? C74 H74 0.9300 . ? C75 C76 1.393(5) . ? C75 H75 0.9300 . ? C76 C77 1.379(5) . ? C76 H76 0.9300 . ? C77 O20 1.374(4) . ? C78 O20 1.428(4) . ? C78 C79 1.499(5) . ? C78 H78A 0.9700 . ? C78 H78B 0.9700 . ? C79 O21 1.434(4) . ? C79 H79A 0.9700 . ? C79 H79B 0.9700 . ? C80 O21 1.436(4) . ? C80 C81 1.495(5) . ? C80 H80A 0.9700 . ? C80 H80B 0.9700 . ? C81 O15 1.439(4) . ? C81 H81A 0.9700 . ? C81 H81B 0.9700 . ? Cl1 O24 1.426(3) . ? Cl1 O25 1.434(3) . ? Cl1 O22 1.437(3) . ? Cl1 O23 1.447(3) . ? Cl2 O27 1.401(3) . ? Cl2 O28 1.418(3) . ? Cl2 O29 1.421(3) . ? Cl2 O26 1.465(3) . ? Cl3 O32 1.404(4) . ? Cl3 O33 1.420(3) . ? Cl3 O31 1.432(3) . ? Cl3 O30 1.432(3) . ? Cl4 O34 1.407(3) . ? Cl4 O35 1.413(5) . ? Cl4 O36 1.421(5) . ? Cl4 O37 1.422(4) . ? Cl5 O40 1.421(3) . ? Cl5 O38 1.424(3) . ? Cl5 O41 1.445(2) . ? Cl5 O39 1.450(3) . ? Cl6 O42 1.416(3) . ? Cl6 O43 1.429(3) . ? Cl6 O44 1.441(3) . ? Cl6 O45 1.444(3) . ? N1 H1NA 0.80(6) . ? N1 H1NB 0.85(7) . ? N1 H1NC 1.02(6) . ? C4 H4 0.9300 . ? N3 H3NA 0.96(4) . ? N3 H3NB 0.96(6) . ? N3 H3NC 0.97(5) . ? N4 H4N 0.99(5) . ? N5 H5NA 0.99(5) . ? N5 H5NB 0.88(4) . ? N5 H5NC 0.96(5) . ? N6 H6N 0.84(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 C2 C1 C5 120.4(4) . . ? C2 C1 N1 121.3(4) . . ? C5 C1 N1 118.2(3) . . ? C1 C2 C4 118.1(4) . . ? C1 C2 H2 120.9 . . ? C4 C2 H2 120.9 . . ? N2 C3 C4 120.8(5) . . ? N2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C3 N2 C5 120.9(4) . . ? N2 C5 C1 120.3(4) . . ? N2 C5 H5 119.9 . . ? C1 C5 H5 119.9 . . ? C7 C6 C10 120.7(3) . . ? C7 C6 N3 118.7(3) . . ? C10 C6 N3 120.6(3) . . ? N4 C7 C6 118.8(3) . . ? N4 C7 H7 120.6 . . ? C6 C7 H7 120.6 . . ? N4 C8 C9 119.8(3) . . ? N4 C8 H8 120.1 . . ? C9 C8 H8 120.1 . . ? C8 C9 C10 119.9(3) . . ? C8 C9 H9 120.1 . . ? C10 C9 H9 120.1 . . ? C6 C10 C9 118.1(3) . . ? C6 C10 H10 121.0 . . ? C9 C10 H10 121.0 . . ? C12 C11 C15 120.5(3) . . ? C12 C11 N5 118.0(3) . . ? C15 C11 N5 121.5(3) . . ? N6 C12 C11 119.1(3) . . ? N6 C12 H12 120.5 . . ? C11 C12 H12 120.5 . . ? N6 C13 C14 119.3(3) . . ? N6 C13 H13 120.3 . . ? C14 C13 H13 120.3 . . ? C13 C14 C15 119.5(3) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? C11 C15 C14 118.8(3) . . ? C11 C15 H15 120.6 . . ? C14 C15 H15 120.6 . . ? C17 C16 O1 125.6(3) . . ? C17 C16 C21 120.6(4) . . ? O1 C16 C21 113.8(3) . . ? C16 C17 C18 119.6(4) . . ? C16 C17 H17 120.2 . . ? C18 C17 H17 120.2 . . ? C19 C18 C17 120.3(4) . . ? C19 C18 H18 119.8 . . ? C17 C18 H18 119.8 . . ? C18 C19 C20 120.5(4) . . ? C18 C19 H19 119.8 . . ? C20 C19 H19 119.8 . . ? C21 C20 C19 119.6(4) . . ? C21 C20 H20 120.2 . . ? C19 C20 H20 120.2 . . ? O2 C21 C20 125.6(4) . . ? O2 C21 C16 115.0(3) . . ? C20 C21 C16 119.4(4) . . ? O2 C22 C23 106.9(3) . . ? O2 C22 H22A 110.3 . . ? C23 C22 H22A 110.3 . . ? O2 C22 H22B 110.3 . . ? C23 C22 H22B 110.3 . . ? H22A C22 H22B 108.6 . . ? O3 C23 C22 106.8(4) . . ? O3 C23 H23A 110.4 . . ? C22 C23 H23A 110.4 . . ? O3 C23 H23B 110.4 . . ? C22 C23 H23B 110.4 . . ? H23A C23 H23B 108.6 . . ? O3 C24 C25 108.2(3) . . ? O3 C24 H24A 110.1 . . ? C25 C24 H24A 110.1 . . ? O3 C24 H24B 110.1 . . ? C25 C24 H24B 110.1 . . ? H24A C24 H24B 108.4 . . ? O4 C25 C24 108.4(3) . . ? O4 C25 H25A 110.0 . . ? C24 C25 H25A 110.0 . . ? O4 C25 H25B 110.0 . . ? C24 C25 H25B 110.0 . . ? H25A C25 H25B 108.4 . . ? O4 C26 C31 115.6(4) . . ? O4 C26 C27 125.1(5) . . ? C31 C26 C27 119.3(4) . . ? C28 C27 C26 119.5(6) . . ? C28 C27 H27 120.2 . . ? C26 C27 H27 120.2 . . ? C29 C28 C27 121.3(6) . . ? C29 C28 H28 119.4 . . ? C27 C28 H28 119.4 . . ? C28 C29 C30 120.6(6) . . ? C28 C29 H29 119.7 . . ? C30 C29 H29 119.7 . . ? C31 C30 C29 118.8(7) . . ? C31 C30 H30 120.6 . . ? C29 C30 H30 120.6 . . ? C30 C31 O5 122.9(5) . . ? C30 C31 C26 120.5(5) . . ? O5 C31 C26 116.6(4) . . ? O5 C32 C33 116.6(6) . . ? O5 C32 H32A 108.2 . . ? C33 C32 H32A 108.2 . . ? O5 C32 H32B 108.2 . . ? C33 C32 H32B 108.2 . . ? H32A C32 H32B 107.3 . . ? O6 C33 C32 112.6(4) . . ? O6 C33 H33A 109.1 . . ? C32 C33 H33A 109.1 . . ? O6 C33 H33B 109.1 . . ? C32 C33 H33B 109.1 . . ? H33A C33 H33B 107.8 . . ? O6 C34 C35 117.3(5) . . ? O6 C34 H34A 108.0 . . ? C35 C34 H34A 108.0 . . ? O6 C34 H34B 108.0 . . ? C35 C34 H34B 108.0 . . ? H34A C34 H34B 107.2 . . ? O7 C35 C34 122.4(4) . . ? O7 C35 H35A 106.7 . . ? C34 C35 H35A 106.7 . . ? O7 C35 H35B 106.7 . . ? C34 C35 H35B 106.7 . . ? H35A C35 H35B 106.6 . . ? O7 C36 C37 109.8(3) . . ? O7 C36 H36A 109.7 . . ? C37 C36 H36A 109.7 . . ? O7 C36 H36B 109.7 . . ? C37 C36 H36B 109.7 . . ? H36A C36 H36B 108.2 . . ? O1 C37 C36 106.2(3) . . ? O1 C37 H37A 110.5 . . ? C36 C37 H37A 110.5 . . ? O1 C37 H37B 110.5 . . ? C36 C37 H37B 110.5 . . ? H37A C37 H37B 108.7 . . ? O8 C38 C39 121.2(3) . . ? O8 C38 C43 118.2(3) . . ? C39 C38 C43 120.5(3) . . ? C38 C39 C40 119.7(3) . . ? C38 C39 H39 120.2 . . ? C40 C39 H39 120.2 . . ? C41 C40 C39 120.1(3) . . ? C41 C40 H40 120.0 . . ? C39 C40 H40 120.0 . . ? C40 C41 C42 120.4(3) . . ? C40 C41 H41 119.8 . . ? C42 C41 H41 119.8 . . ? C41 C42 C43 120.0(3) . . ? C41 C42 H42 120.0 . . ? C43 C42 H42 120.0 . . ? O9 C43 C42 125.1(3) . . ? O9 C43 C38 115.7(3) . . ? C42 C43 C38 119.2(3) . . ? O9 C44 C45 107.2(3) . . ? O9 C44 H44A 110.3 . . ? C45 C44 H44A 110.3 . . ? O9 C44 H44B 110.3 . . ? C45 C44 H44B 110.3 . . ? H44A C44 H44B 108.5 . . ? O10 C45 C44 108.0(3) . . ? O10 C45 H45A 110.1 . . ? C44 C45 H45A 110.1 . . ? O10 C45 H45B 110.1 . . ? C44 C45 H45B 110.1 . . ? H45A C45 H45B 108.4 . . ? O10 C46 C47 109.3(2) . . ? O10 C46 H46A 109.8 . . ? C47 C46 H46A 109.8 . . ? O10 C46 H46B 109.8 . . ? C47 C46 H46B 109.8 . . ? H46A C46 H46B 108.3 . . ? O11 C47 C46 107.3(3) . . ? O11 C47 H47A 110.2 . . ? C46 C47 H47A 110.2 . . ? O11 C47 H47B 110.2 . . ? C46 C47 H47B 110.2 . . ? H47A C47 H47B 108.5 . . ? O11 C48 C49 125.2(3) . . ? O11 C48 C53 114.7(3) . . ? C49 C48 C53 120.0(3) . . ? C48 C49 C50 119.4(4) . . ? C48 C49 H49 120.3 . . ? C50 C49 H49 120.3 . . ? C51 C50 C49 120.4(4) . . ? C51 C50 H50 119.8 . . ? C49 C50 H50 119.8 . . ? C50 C51 C52 120.7(4) . . ? C50 C51 H51 119.7 . . ? C52 C51 H51 119.7 . . ? C53 C52 C51 119.4(4) . . ? C53 C52 H52 120.3 . . ? C51 C52 H52 120.3 . . ? O12 C53 C52 124.7(4) . . ? O12 C53 C48 115.2(3) . . ? C52 C53 C48 120.1(4) . . ? O12 C54 C55 108.1(3) . . ? O12 C54 H54A 110.1 . . ? C55 C54 H54A 110.1 . . ? O12 C54 H54B 110.1 . . ? C55 C54 H54B 110.1 . . ? H54A C54 H54B 108.4 . . ? O13 C55 C54 108.9(3) . . ? O13 C55 H55A 109.9 . . ? C54 C55 H55A 109.9 . . ? O13 C55 H55B 109.9 . . ? C54 C55 H55B 109.9 . . ? H55A C55 H55B 108.3 . . ? O13 C56 C57 108.9(3) . . ? O13 C56 H56A 109.9 . . ? C57 C56 H56A 109.9 . . ? O13 C56 H56B 109.9 . . ? C57 C56 H56B 109.9 . . ? H56A C56 H56B 108.3 . . ? O14 C57 C56 108.7(3) . . ? O14 C57 H57A 110.0 . . ? C56 C57 H57A 110.0 . . ? O14 C57 H57B 110.0 . . ? C56 C57 H57B 110.0 . . ? H57A C57 H57B 108.3 . . ? C59 C58 O14 117.4(5) . . ? C59 C58 H58A 108.0 . . ? O14 C58 H58A 108.0 . . ? C59 C58 H58B 108.0 . . ? O14 C58 H58B 108.0 . . ? H58A C58 H58B 107.2 . . ? C58 C59 O8 129.1(7) . . ? C58 C59 H59A 105.0 . . ? O8 C59 H59A 105.0 . . ? C58 C59 H59B 105.0 . . ? O8 C59 H59B 105.0 . . ? H59A C59 H59B 105.9 . . ? O15 C60 C61 125.1(3) . . ? O15 C60 C65 115.4(3) . . ? C61 C60 C65 119.3(3) . . ? C62 C61 C60 119.9(4) . . ? C62 C61 H61 120.0 . . ? C60 C61 H61 120.0 . . ? C61 C62 C63 120.9(4) . . ? C61 C62 H62 119.5 . . ? C63 C62 H62 119.5 . . ? C62 C63 C64 119.2(4) . . ? C62 C63 H63 120.4 . . ? C64 C63 H63 120.4 . . ? C65 C64 C63 120.3(4) . . ? C65 C64 H64 119.9 . . ? C63 C64 H64 119.9 . . ? C64 C65 O16 118.0(3) . . ? C64 C65 C60 120.4(3) . . ? O16 C65 C60 121.2(3) . . ? O16 C66 C67 105.9(3) . . ? O16 C66 H66A 110.5 . . ? C67 C66 H66A 110.5 . . ? O16 C66 H66B 110.5 . . ? C67 C66 H66B 110.5 . . ? H66A C66 H66B 108.7 . . ? O17 C67 C66 108.9(3) . . ? O17 C67 H67A 109.9 . . ? C66 C67 H67A 109.9 . . ? O17 C67 H67B 109.9 . . ? C66 C67 H67B 109.9 . . ? H67A C67 H67B 108.3 . . ? O17 C68 C69 110.5(3) . . ? O17 C68 H68A 109.5 . . ? C69 C68 H68A 109.5 . . ? O17 C68 H68B 109.5 . . ? C69 C68 H68B 109.5 . . ? H68A C68 H68B 108.1 . . ? O18 C69 C68 109.7(3) . . ? O18 C69 H69A 109.7 . . ? C68 C69 H69A 109.7 . . ? O18 C69 H69B 109.7 . . ? C68 C69 H69B 109.7 . . ? H69A C69 H69B 108.2 . . ? O18 C70 C71 107.8(3) . . ? O18 C70 H70A 110.2 . . ? C71 C70 H70A 110.2 . . ? O18 C70 H70B 110.2 . . ? C71 C70 H70B 110.2 . . ? H70A C70 H70B 108.5 . . ? O19 C71 C70 106.4(3) . . ? O19 C71 H71A 110.4 . . ? C70 C71 H71A 110.4 . . ? O19 C71 H71B 110.4 . . ? C70 C71 H71B 110.4 . . ? H71A C71 H71B 108.6 . . ? O19 C72 C73 124.8(3) . . ? O19 C72 C77 114.9(3) . . ? C73 C72 C77 120.3(3) . . ? C72 C73 C74 119.3(3) . . ? C72 C73 H73 120.4 . . ? C74 C73 H73 120.4 . . ? C75 C74 C73 120.6(3) . . ? C75 C74 H74 119.7 . . ? C73 C74 H74 119.7 . . ? C74 C75 C76 120.6(3) . . ? C74 C75 H75 119.7 . . ? C76 C75 H75 119.7 . . ? C77 C76 C75 119.6(3) . . ? C77 C76 H76 120.2 . . ? C75 C76 H76 120.2 . . ? O20 C77 C76 124.9(3) . . ? O20 C77 C72 115.3(3) . . ? C76 C77 C72 119.8(3) . . ? O20 C78 C79 107.1(3) . . ? O20 C78 H78A 110.3 . . ? C79 C78 H78A 110.3 . . ? O20 C78 H78B 110.3 . . ? C79 C78 H78B 110.3 . . ? H78A C78 H78B 108.5 . . ? O21 C79 C78 106.6(3) . . ? O21 C79 H79A 110.4 . . ? C78 C79 H79A 110.4 . . ? O21 C79 H79B 110.4 . . ? C78 C79 H79B 110.4 . . ? H79A C79 H79B 108.6 . . ? O21 C80 C81 106.0(3) . . ? O21 C80 H80A 110.5 . . ? C81 C80 H80A 110.5 . . ? O21 C80 H80B 110.5 . . ? C81 C80 H80B 110.5 . . ? H80A C80 H80B 108.7 . . ? O15 C81 C80 106.9(3) . . ? O15 C81 H81A 110.3 . . ? C80 C81 H81A 110.3 . . ? O15 C81 H81B 110.3 . . ? C80 C81 H81B 110.3 . . ? H81A C81 H81B 108.6 . . ? O24 Cl1 O25 110.04(17) . . ? O24 Cl1 O22 110.21(16) . . ? O25 Cl1 O22 109.07(16) . . ? O24 Cl1 O23 109.63(17) . . ? O25 Cl1 O23 109.68(18) . . ? O22 Cl1 O23 108.18(15) . . ? O27 Cl2 O28 110.8(2) . . ? O27 Cl2 O29 111.5(2) . . ? O28 Cl2 O29 110.19(18) . . ? O27 Cl2 O26 108.6(2) . . ? O28 Cl2 O26 107.52(19) . . ? O29 Cl2 O26 108.02(16) . . ? O32 Cl3 O33 108.9(2) . . ? O32 Cl3 O31 110.2(3) . . ? O33 Cl3 O31 108.7(2) . . ? O32 Cl3 O30 110.2(2) . . ? O33 Cl3 O30 110.36(17) . . ? O31 Cl3 O30 108.49(18) . . ? O34 Cl4 O35 111.2(3) . . ? O34 Cl4 O36 108.4(3) . . ? O35 Cl4 O36 107.6(4) . . ? O34 Cl4 O37 109.4(3) . . ? O35 Cl4 O37 109.7(3) . . ? O36 Cl4 O37 110.5(4) . . ? O40 Cl5 O38 110.88(17) . . ? O40 Cl5 O41 109.54(16) . . ? O38 Cl5 O41 109.62(15) . . ? O40 Cl5 O39 109.55(17) . . ? O38 Cl5 O39 108.98(17) . . ? O41 Cl5 O39 108.22(15) . . ? O42 Cl6 O43 110.94(18) . . ? O42 Cl6 O44 109.09(17) . . ? O43 Cl6 O44 108.11(18) . . ? O42 Cl6 O45 110.23(17) . . ? O43 Cl6 O45 110.22(18) . . ? O44 Cl6 O45 108.18(16) . . ? C1 N1 H1NA 104(4) . . ? C1 N1 H1NB 112(4) . . ? H1NA N1 H1NB 118(6) . . ? C1 N1 H1NC 116(3) . . ? H1NA N1 H1NC 107(5) . . ? H1NB N1 H1NC 101(5) . . ? C2 C4 C3 119.4(5) . . ? C2 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? C6 N3 H3NA 108(2) . . ? C6 N3 H3NB 109(3) . . ? H3NA N3 H3NB 109(4) . . ? C6 N3 H3NC 113(3) . . ? H3NA N3 H3NC 115(4) . . ? H3NB N3 H3NC 103(4) . . ? C7 N4 C8 122.7(3) . . ? C7 N4 H4N 121(3) . . ? C8 N4 H4N 116(3) . . ? C11 N5 H5NA 112(2) . . ? C11 N5 H5NB 113(2) . . ? H5NA N5 H5NB 109(3) . . ? C11 N5 H5NC 114(3) . . ? H5NA N5 H5NC 104(4) . . ? H5NB N5 H5NC 105(4) . . ? C12 N6 C13 122.7(3) . . ? C12 N6 H6N 121(3) . . ? C13 N6 H6N 117(3) . . ? C16 O1 C37 117.5(3) . . ? C21 O2 C22 117.8(3) . . ? C24 O3 C23 113.6(3) . . ? C26 O4 C25 116.4(3) . . ? C32 O5 C31 118.3(4) . . ? C33 O6 C34 117.5(4) . . ? C35 O7 C36 118.7(4) . . ? C59 O8 C38 119.7(3) . . ? C43 O9 C44 116.8(2) . . ? C45 O10 C46 114.3(2) . . ? C48 O11 C47 116.9(3) . . ? C53 O12 C54 117.4(3) . . ? C55 O13 C56 111.8(3) . . ? C57 O14 C58 112.8(4) . . ? C60 O15 C81 118.3(3) . . ? C65 O16 C66 117.5(3) . . ? C68 O17 C67 110.6(3) . . ? C70 O18 C69 111.7(2) . . ? C72 O19 C71 117.5(3) . . ? C77 O20 C78 118.6(2) . . ? C79 O21 C80 116.9(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N5 H5NB O17 0.88(4) 2.03(4) 2.889(4) 165(3) 2_666 N5 H5NC O19 0.96(5) 2.17(5) 2.947(4) 137(4) 2_666 N5 H5NA O21 0.99(5) 1.80(5) 2.775(4) 168(4) 2_666 N6 H6N O44 0.84(4) 2.09(4) 2.869(4) 154(3) . N3 H3NA O10 0.96(4) 1.90(4) 2.829(4) 161(3) . N3 H3NB O12 0.96(6) 2.13(6) 2.947(4) 142(4) . N3 H3NC O14 0.97(5) 1.88(5) 2.833(4) 166(4) . N4 H4N O26 0.99(5) 1.95(5) 2.852(4) 151(4) 2_666 N1 H1NC O3 1.02(6) 1.86(6) 2.866(4) 167(5) . N1 H1NB O5 0.85(7) 2.33(7) 2.999(5) 135(5) . N1 H1NA O7 0.80(6) 2.40(5) 3.031(5) 137(5) . N1 H1NA O1 0.80(6) 2.45(6) 3.081(5) 137(5) . C68 H68A O40 0.97 2.51 3.461(4) 166.8 2_566 C71 H71A O29 0.97 2.60 3.431(4) 144.0 1_545 C78 H78A O32 0.97 2.41 3.353(5) 163.2 . C75 H75 O40 0.93 2.50 3.379(4) 158.0 2_666 C41 H41 O41 0.93 2.56 3.425(4) 155.3 1_545 C47 H47A O43 0.97 2.58 3.498(4) 156.8 2_667 C47 H47B O22 0.97 2.65 3.562(4) 157.1 1_546 C54 H54A O23 0.97 2.60 3.552(4) 168.0 2_666 C39 H39 O27 0.93 2.57 3.380(5) 146.0 2_666 C58 H58B O33 0.97 2.39 3.292(6) 154.9 2_666 C14 H14 O33 0.93 2.40 3.259(5) 153.3 2_666 C15 H15 O21 0.93 2.57 3.277(4) 133.1 2_666 C15 H15 O32 0.93 2.60 3.292(5) 131.9 2_666 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.265 _refine_diff_density_min -1.005 _refine_diff_density_rms 0.080 #END*********************************************************** data_DADPE-18C6-ClO4 _database_code_depnum_ccdc_archive 'CCDC 846230' #TrackingRef '- Structures(3).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C12 H24 O6), (C12 H14 N2 O), 2(C2 H3 N), 2(Cl O4)' _chemical_formula_sum 'C40 H68 Cl2 N4 O21' _chemical_formula_weight 1011.88 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.2134(7) _cell_length_b 13.2564(8) _cell_length_c 17.0677(10) _cell_angle_alpha 75.025(1) _cell_angle_beta 71.730(1) _cell_angle_gamma 72.189(1) _cell_volume 2457.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8382 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 25.06 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.367 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1076 _exptl_absorpt_coefficient_mu 0.213 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.9196 _exptl_absorpt_correction_T_max 0.9831 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD 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 22380 _diffrn_reflns_av_R_equivalents 0.0263 _diffrn_reflns_av_sigmaI/netI 0.0326 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.28 _diffrn_reflns_theta_max 25.00 _reflns_number_total 8631 _reflns_number_gt 7165 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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. ; _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^)+(0.0587P)^2^+1.5849P] 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 8631 _refine_ls_number_parameters 630 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0551 _refine_ls_R_factor_gt 0.0447 _refine_ls_wR_factor_ref 0.1187 _refine_ls_wR_factor_gt 0.1118 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 Cl2 Cl 0.37189(5) 0.41394(4) 0.39472(3) 0.02585(14) Uani 1 1 d . . . O10 O -0.17565(12) 0.53357(11) 0.82757(9) 0.0250(3) Uani 1 1 d . . . O12 O 0.07101(13) 0.19787(11) 0.90899(9) 0.0243(3) Uani 1 1 d . . . O3 O 0.45435(13) 1.13587(12) 0.13419(9) 0.0297(4) Uani 1 1 d . . . O9 O 0.01247(13) 0.60375(11) 0.69206(9) 0.0258(3) Uani 1 1 d . . . O5 O 0.52977(12) 0.94613(11) 0.39929(9) 0.0248(3) Uani 1 1 d . . . O7 O 0.30233(13) 0.82017(11) 0.27864(9) 0.0258(3) Uani 1 1 d . . . O11 O -0.16848(13) 0.31822(12) 0.90909(9) 0.0261(3) Uani 1 1 d . . . O13 O 0.26514(12) 0.23440(11) 0.77768(9) 0.0239(3) Uani 1 1 d . . . O8 O 0.23698(12) 0.45442(11) 0.69348(9) 0.0238(3) Uani 1 1 d . . . O1 O -0.02015(12) 0.21266(12) 0.51245(9) 0.0264(3) Uani 1 1 d . . . O4 O 0.60048(13) 1.07470(12) 0.24379(9) 0.0277(3) Uani 1 1 d . . . O6 O 0.40868(13) 0.79511(12) 0.40909(9) 0.0265(3) Uani 1 1 d . . . O2 O 0.36453(15) 0.96383(13) 0.12771(10) 0.0346(4) Uani 1 1 d . . . N1 N 0.37699(16) -0.00083(15) 0.29216(12) 0.0195(4) Uani 1 1 d . . . N2 N 0.03076(17) 0.37345(14) 0.76865(11) 0.0193(4) Uani 1 1 d . . . C4 C 0.08131(17) 0.16189(16) 0.45896(12) 0.0197(4) Uani 1 1 d . . . C1 C 0.27230(17) 0.05790(15) 0.34817(12) 0.0179(4) Uani 1 1 d . . . C8 C -0.03075(19) 0.36215(17) 0.57086(13) 0.0240(5) Uani 1 1 d . . . H8 H -0.0555 0.4099 0.5241 0.029 Uiso 1 1 calc R . . C5 C 0.18991(18) 0.18650(16) 0.44074(12) 0.0208(4) Uani 1 1 d . . . H5 H 0.1984 0.2384 0.4663 0.025 Uiso 1 1 calc R . . C35 C 0.36066(19) 0.28504(17) 0.73759(14) 0.0286(5) Uani 1 1 d . . . H35A H 0.4346 0.2304 0.7189 0.034 Uiso 1 1 calc R . . H35B H 0.3735 0.3198 0.7777 0.034 Uiso 1 1 calc R . . C10 C 0.01566(17) 0.33123(16) 0.70240(12) 0.0187(4) Uani 1 1 d . . . C25 C 0.2201(2) 0.54763(17) 0.62932(14) 0.0269(5) Uani 1 1 d . . . H25A H 0.1982 0.5301 0.5841 0.032 Uiso 1 1 calc R . . H25B H 0.2945 0.5722 0.6047 0.032 Uiso 1 1 calc R . . C7 C -0.00442(17) 0.25207(17) 0.57567(13) 0.0216(4) Uani 1 1 d . . . C2 C 0.16310(17) 0.03554(15) 0.36500(12) 0.0190(4) Uani 1 1 d . . . H2 H 0.1543 -0.0155 0.3387 0.023 Uiso 1 1 calc R . . C6 C 0.28615(17) 0.13391(16) 0.38442(12) 0.0198(4) Uani 1 1 d . . . H6 H 0.3613 0.1500 0.3708 0.024 Uiso 1 1 calc R . . C9 C -0.02066(18) 0.40223(17) 0.63517(13) 0.0231(4) Uani 1 1 d . . . H9 H -0.0386 0.4777 0.6329 0.028 Uiso 1 1 calc R . . C11 C 0.03977(18) 0.22091(16) 0.70772(13) 0.0223(4) Uani 1 1 d . . . H11 H 0.0634 0.1731 0.7548 0.027 Uiso 1 1 calc R . . C12 C 0.02916(18) 0.18090(17) 0.64384(13) 0.0244(5) Uani 1 1 d . . . H12 H 0.0448 0.1054 0.6469 0.029 Uiso 1 1 calc R . . C3 C 0.06655(18) 0.08838(15) 0.42065(12) 0.0190(4) Uani 1 1 d . . . H3 H -0.0093 0.0743 0.4325 0.023 Uiso 1 1 calc R . . C22 C 0.3203(2) 0.72209(17) 0.33818(15) 0.0291(5) Uani 1 1 d . . . H22A H 0.3991 0.6746 0.3174 0.035 Uiso 1 1 calc R . . H22B H 0.2586 0.6839 0.3456 0.035 Uiso 1 1 calc R . . C18 C 0.64670(19) 0.96385(19) 0.36839(14) 0.0297(5) Uani 1 1 d . . . H18A H 0.6999 0.9079 0.3354 0.036 Uiso 1 1 calc R . . H18B H 0.6791 0.9593 0.4159 0.036 Uiso 1 1 calc R . . C29 C -0.27986(19) 0.49314(19) 0.86002(15) 0.0307(5) Uani 1 1 d . . . H29A H -0.2920 0.4633 0.8167 0.037 Uiso 1 1 calc R . . H29B H -0.3505 0.5519 0.8765 0.037 Uiso 1 1 calc R . . C34 C 0.28054(19) 0.16631(17) 0.85461(13) 0.0258(5) Uani 1 1 d . . . H34A H 0.2844 0.2089 0.8931 0.031 Uiso 1 1 calc R . . H34B H 0.3559 0.1100 0.8445 0.031 Uiso 1 1 calc R . . C36 C 0.33258(19) 0.36815(17) 0.66330(14) 0.0289(5) Uani 1 1 d . . . H36A H 0.4035 0.3955 0.6302 0.035 Uiso 1 1 calc R . . H36B H 0.3093 0.3358 0.6267 0.035 Uiso 1 1 calc R . . C28 C -0.19118(19) 0.63388(16) 0.76920(14) 0.0267(5) Uani 1 1 d . . . H28A H -0.2592 0.6882 0.7957 0.032 Uiso 1 1 calc R . . H28B H -0.2080 0.6234 0.7191 0.032 Uiso 1 1 calc R . . C31 C -0.1346(2) 0.24436(18) 0.97963(13) 0.0290(5) Uani 1 1 d . . . H31A H -0.2024 0.2142 1.0157 0.035 Uiso 1 1 calc R . . H31B H -0.1130 0.2826 1.0132 0.035 Uiso 1 1 calc R . . C20 C 0.4094(2) 0.82545(18) 0.48280(13) 0.0300(5) Uani 1 1 d . . . H20A H 0.4027 0.7647 0.5306 0.036 Uiso 1 1 calc R . . H20B H 0.3412 0.8873 0.4967 0.036 Uiso 1 1 calc R . . C27 C -0.0797(2) 0.67199(16) 0.74405(14) 0.0270(5) Uani 1 1 d . . . H27A H -0.0938 0.7471 0.7131 0.032 Uiso 1 1 calc R . . H27B H -0.0555 0.6704 0.7947 0.032 Uiso 1 1 calc R . . C33 C 0.17775(19) 0.11506(16) 0.89317(14) 0.0245(5) Uani 1 1 d . . . H33A H 0.1736 0.0727 0.8546 0.029 Uiso 1 1 calc R . . H33B H 0.1881 0.0657 0.9463 0.029 Uiso 1 1 calc R . . C32 C -0.0305(2) 0.15469(17) 0.95090(14) 0.0292(5) Uani 1 1 d . . . H32A H -0.0142 0.0986 0.9997 0.035 Uiso 1 1 calc R . . H32B H -0.0485 0.1214 0.9122 0.035 Uiso 1 1 calc R . . C16 C 0.5823(2) 1.17963(18) 0.19381(15) 0.0312(5) Uani 1 1 d . . . H16A H 0.6536 1.2077 0.1806 0.037 Uiso 1 1 calc R . . H16B H 0.5136 1.2293 0.2247 0.037 Uiso 1 1 calc R . . C26 C 0.12254(19) 0.63440(17) 0.66848(15) 0.0274(5) Uani 1 1 d . . . H26A H 0.1395 0.6447 0.7185 0.033 Uiso 1 1 calc R . . H26B H 0.1174 0.7032 0.6280 0.033 Uiso 1 1 calc R . . C21 C 0.31333(19) 0.74762(18) 0.42027(14) 0.0298(5) Uani 1 1 d . . . H21A H 0.2362 0.7982 0.4397 0.036 Uiso 1 1 calc R . . H21B H 0.3196 0.6809 0.4630 0.036 Uiso 1 1 calc R . . C19 C 0.5236(2) 0.85566(17) 0.46655(14) 0.0282(5) Uani 1 1 d . . . H19A H 0.5284 0.8742 0.5178 0.034 Uiso 1 1 calc R . . H19B H 0.5914 0.7940 0.4516 0.034 Uiso 1 1 calc R . . C17 C 0.6409(2) 1.07287(19) 0.31429(14) 0.0303(5) Uani 1 1 d . . . H17A H 0.5854 1.1287 0.3466 0.036 Uiso 1 1 calc R . . H17B H 0.7205 1.0881 0.2950 0.036 Uiso 1 1 calc R . . C23 C 0.3071(2) 0.80098(19) 0.19902(15) 0.0334(5) Uani 1 1 d . . . H23A H 0.2507 0.7575 0.2057 0.040 Uiso 1 1 calc R . . H23B H 0.3882 0.7609 0.1735 0.040 Uiso 1 1 calc R . . C30 C -0.2636(2) 0.40665(18) 0.93490(14) 0.0307(5) Uani 1 1 d . . . H30A H -0.2456 0.4355 0.9762 0.037 Uiso 1 1 calc R . . H30B H -0.3378 0.3822 0.9620 0.037 Uiso 1 1 calc R . . C15 C 0.5595(2) 1.17256(18) 0.11490(14) 0.0310(5) Uani 1 1 d . . . H15A H 0.5501 1.2443 0.0782 0.037 Uiso 1 1 calc R . . H15B H 0.6279 1.1220 0.0846 0.037 Uiso 1 1 calc R . . C24 C 0.2749(2) 0.9072(2) 0.14417(16) 0.0382(6) Uani 1 1 d . . . H24A H 0.2684 0.8961 0.0908 0.046 Uiso 1 1 calc R . . H24B H 0.1970 0.9499 0.1723 0.046 Uiso 1 1 calc R . . C14 C 0.4348(3) 1.1212(2) 0.06054(16) 0.0475(7) Uani 1 1 d . . . H14A H 0.5067 1.0736 0.0303 0.057 Uiso 1 1 calc R . . H14B H 0.4183 1.1915 0.0228 0.057 Uiso 1 1 calc R . . C13 C 0.3314(3) 1.0718(2) 0.08481(19) 0.0534(8) Uani 1 1 d . . . H13A H 0.2626 1.1140 0.1218 0.064 Uiso 1 1 calc R . . H13B H 0.3083 1.0720 0.0341 0.064 Uiso 1 1 calc R . . Cl1 Cl 0.94527(5) 0.12986(5) 0.19118(4) 0.03749(16) Uani 1 1 d . . . O14 O 0.85954(18) 0.22808(14) 0.18284(12) 0.0497(5) Uani 1 1 d . . . O16 O 0.9136(2) 0.04917(18) 0.16816(14) 0.0737(7) Uani 1 1 d . . . O15 O 0.9496(3) 0.09742(18) 0.27603(18) 0.0899(9) Uani 1 1 d . . . O17 O 1.0542(2) 0.1452(2) 0.1379(3) 0.1447(17) Uani 1 1 d . . . O21 O 0.43740(15) 0.31115(12) 0.37119(11) 0.0382(4) Uani 1 1 d . . . O19 O 0.44583(17) 0.45852(15) 0.41959(12) 0.0482(5) Uani 1 1 d . . . O18 O 0.33306(19) 0.48459(14) 0.32459(12) 0.0495(5) Uani 1 1 d . . . O20 O 0.27057(16) 0.39955(15) 0.46312(12) 0.0471(5) Uani 1 1 d . . . N3 N 0.5612(2) 0.6010(2) 0.07496(15) 0.0509(6) Uani 1 1 d . . . C38 C 0.5914(2) 0.5357(2) 0.12694(16) 0.0347(5) Uani 1 1 d . . . C37 C 0.6325(2) 0.4519(2) 0.19299(17) 0.0420(6) Uani 1 1 d . . . H37A H 0.6939 0.3935 0.1679 0.063 Uiso 1 1 calc R . . H37B H 0.5655 0.4237 0.2310 0.063 Uiso 1 1 calc R . . H37C H 0.6656 0.4822 0.2244 0.063 Uiso 1 1 calc R . . N4 N 0.0943(2) 0.4713(2) 0.88660(16) 0.0522(6) Uani 1 1 d . . . C39 C 0.1167(2) 0.4198(2) 0.94561(18) 0.0441(6) Uani 1 1 d . . . C40 C 0.1469(3) 0.3520(2) 1.02227(18) 0.0556(8) Uani 1 1 d . . . H40A H 0.2328 0.3198 1.0104 0.083 Uiso 1 1 calc R . . H40B H 0.1042 0.2948 1.0420 0.083 Uiso 1 1 calc R . . H40C H 0.1240 0.3961 1.0656 0.083 Uiso 1 1 calc R . . H2NA H 0.094(2) 0.4037(19) 0.7486(15) 0.027(6) Uiso 1 1 d . . . H1NB H 0.435(2) -0.0229(19) 0.3178(15) 0.027(6) Uiso 1 1 d . . . H1NA H 0.359(2) -0.058(2) 0.2817(15) 0.030(6) Uiso 1 1 d . . . H1NC H 0.402(2) 0.039(2) 0.2438(18) 0.038(7) Uiso 1 1 d . . . H2NB H 0.048(2) 0.322(2) 0.8125(17) 0.039(7) Uiso 1 1 d . . . H2NC H -0.038(3) 0.422(2) 0.7907(17) 0.046(8) 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 Cl2 0.0324(3) 0.0181(3) 0.0297(3) -0.0038(2) -0.0126(2) -0.0055(2) O10 0.0231(8) 0.0195(7) 0.0285(8) -0.0001(6) -0.0078(6) -0.0021(6) O12 0.0255(8) 0.0173(7) 0.0264(8) -0.0012(6) -0.0046(6) -0.0042(6) O3 0.0289(8) 0.0296(8) 0.0295(8) 0.0024(7) -0.0083(7) -0.0111(7) O9 0.0241(8) 0.0195(7) 0.0349(8) -0.0050(6) -0.0092(7) -0.0050(6) O5 0.0196(7) 0.0250(8) 0.0269(8) -0.0025(6) -0.0076(6) -0.0015(6) O7 0.0259(8) 0.0195(7) 0.0327(8) -0.0066(6) -0.0072(7) -0.0052(6) O11 0.0269(8) 0.0247(8) 0.0234(8) -0.0019(6) -0.0054(6) -0.0049(6) O13 0.0245(8) 0.0213(7) 0.0246(8) -0.0008(6) -0.0078(6) -0.0047(6) O8 0.0227(8) 0.0182(7) 0.0260(8) -0.0003(6) -0.0051(6) -0.0028(6) O1 0.0163(7) 0.0392(9) 0.0268(8) -0.0186(7) -0.0038(6) -0.0026(6) O4 0.0283(8) 0.0274(8) 0.0293(8) -0.0054(6) -0.0060(7) -0.0105(7) O6 0.0232(8) 0.0257(8) 0.0274(8) -0.0023(6) -0.0038(6) -0.0061(6) O2 0.0387(9) 0.0398(9) 0.0322(9) -0.0001(7) -0.0156(7) -0.0179(8) N1 0.0171(9) 0.0180(9) 0.0220(10) -0.0034(8) -0.0039(8) -0.0036(7) N2 0.0217(10) 0.0162(9) 0.0195(9) -0.0022(7) -0.0062(8) -0.0036(8) C4 0.0189(10) 0.0206(10) 0.0177(10) -0.0037(8) -0.0061(8) -0.0005(8) C1 0.0183(10) 0.0148(9) 0.0167(10) -0.0009(8) -0.0049(8) 0.0001(8) C8 0.0249(11) 0.0268(11) 0.0197(10) 0.0004(8) -0.0072(9) -0.0078(9) C5 0.0218(11) 0.0202(10) 0.0224(11) -0.0061(8) -0.0073(9) -0.0043(8) C35 0.0206(11) 0.0241(11) 0.0345(13) -0.0018(9) -0.0040(10) -0.0023(9) C10 0.0152(10) 0.0215(10) 0.0187(10) -0.0068(8) -0.0016(8) -0.0037(8) C25 0.0272(12) 0.0234(11) 0.0277(12) 0.0039(9) -0.0086(9) -0.0084(9) C7 0.0131(10) 0.0307(11) 0.0224(10) -0.0123(9) -0.0017(8) -0.0039(8) C2 0.0218(10) 0.0156(10) 0.0199(10) -0.0010(8) -0.0070(8) -0.0051(8) C6 0.0161(10) 0.0207(10) 0.0219(10) -0.0010(8) -0.0060(8) -0.0046(8) C9 0.0261(11) 0.0190(10) 0.0242(11) -0.0028(8) -0.0070(9) -0.0059(9) C11 0.0225(11) 0.0207(10) 0.0230(11) -0.0028(8) -0.0081(9) -0.0031(8) C12 0.0218(11) 0.0198(10) 0.0324(12) -0.0102(9) -0.0082(9) -0.0008(8) C3 0.0176(10) 0.0194(10) 0.0197(10) -0.0002(8) -0.0067(8) -0.0047(8) C22 0.0216(11) 0.0172(10) 0.0455(14) -0.0020(10) -0.0062(10) -0.0062(9) C18 0.0190(11) 0.0390(13) 0.0318(12) -0.0115(10) -0.0075(9) -0.0028(10) C29 0.0208(11) 0.0316(12) 0.0341(13) -0.0009(10) -0.0053(10) -0.0042(9) C34 0.0274(12) 0.0215(11) 0.0276(11) -0.0011(9) -0.0125(9) -0.0020(9) C36 0.0239(11) 0.0241(11) 0.0299(12) -0.0024(9) -0.0006(9) -0.0019(9) C28 0.0263(12) 0.0192(11) 0.0290(12) -0.0014(9) -0.0095(10) 0.0023(9) C31 0.0308(12) 0.0268(12) 0.0228(11) 0.0039(9) -0.0036(9) -0.0083(10) C20 0.0330(13) 0.0265(12) 0.0231(11) -0.0002(9) -0.0059(10) -0.0021(10) C27 0.0343(12) 0.0157(10) 0.0296(12) -0.0028(9) -0.0114(10) -0.0019(9) C33 0.0285(12) 0.0174(10) 0.0266(11) -0.0009(8) -0.0113(9) -0.0024(9) C32 0.0307(12) 0.0218(11) 0.0304(12) 0.0015(9) -0.0033(10) -0.0096(9) C16 0.0304(12) 0.0265(12) 0.0359(13) -0.0049(10) -0.0014(10) -0.0135(10) C26 0.0289(12) 0.0187(10) 0.0355(12) 0.0020(9) -0.0129(10) -0.0079(9) C21 0.0233(11) 0.0235(11) 0.0359(13) 0.0044(9) -0.0032(10) -0.0090(9) C19 0.0314(12) 0.0239(11) 0.0259(12) -0.0027(9) -0.0115(10) 0.0007(9) C17 0.0242(12) 0.0402(13) 0.0320(12) -0.0120(10) -0.0036(10) -0.0146(10) C23 0.0314(13) 0.0351(13) 0.0402(14) -0.0158(11) -0.0071(11) -0.0116(10) C30 0.0229(11) 0.0305(12) 0.0316(12) -0.0028(10) -0.0022(10) -0.0036(9) C15 0.0298(12) 0.0266(12) 0.0330(12) -0.0004(10) -0.0018(10) -0.0121(10) C24 0.0403(14) 0.0481(15) 0.0373(14) -0.0050(11) -0.0173(12) -0.0210(12) C14 0.0628(18) 0.0554(17) 0.0333(14) 0.0163(12) -0.0261(13) -0.0330(15) C13 0.0652(19) 0.0571(18) 0.0513(17) 0.0216(14) -0.0423(16) -0.0317(15) Cl1 0.0269(3) 0.0270(3) 0.0599(4) -0.0161(3) -0.0030(3) -0.0099(2) O14 0.0601(12) 0.0361(10) 0.0532(12) -0.0050(9) -0.0300(10) 0.0010(9) O16 0.112(2) 0.0633(14) 0.0585(13) -0.0350(11) 0.0171(13) -0.0594(14) O15 0.148(3) 0.0454(13) 0.115(2) 0.0048(13) -0.110(2) -0.0139(14) O17 0.0479(15) 0.0747(19) 0.267(5) -0.056(2) 0.063(2) -0.0367(14) O21 0.0461(10) 0.0210(8) 0.0429(10) -0.0077(7) -0.0110(8) -0.0002(7) O19 0.0509(11) 0.0475(11) 0.0618(12) -0.0152(9) -0.0251(10) -0.0187(9) O18 0.0781(14) 0.0278(9) 0.0483(11) 0.0022(8) -0.0386(11) -0.0056(9) O20 0.0429(11) 0.0480(11) 0.0488(11) -0.0188(9) 0.0044(9) -0.0170(9) N3 0.0457(14) 0.0476(14) 0.0520(15) -0.0074(12) -0.0123(12) -0.0025(11) C38 0.0299(13) 0.0317(13) 0.0411(14) -0.0137(11) -0.0034(11) -0.0056(10) C37 0.0465(16) 0.0317(13) 0.0492(16) -0.0062(12) -0.0136(13) -0.0112(12) N4 0.0510(15) 0.0578(16) 0.0475(15) -0.0161(13) -0.0098(12) -0.0102(12) C39 0.0471(16) 0.0484(16) 0.0428(16) -0.0161(13) -0.0118(13) -0.0134(13) C40 0.064(2) 0.0537(18) 0.0473(17) -0.0149(14) -0.0144(15) -0.0073(15) _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 Cl2 O18 1.4282(17) . ? Cl2 O19 1.4288(17) . ? Cl2 O20 1.4332(18) . ? Cl2 O21 1.4397(16) . ? O10 C29 1.427(3) . ? O10 C28 1.441(2) . ? O12 C33 1.426(2) . ? O12 C32 1.429(3) . ? O3 C14 1.420(3) . ? O3 C15 1.424(3) . ? O9 C27 1.428(3) . ? O9 C26 1.430(3) . ? O5 C18 1.429(3) . ? O5 C19 1.432(3) . ? O7 C23 1.426(3) . ? O7 C22 1.433(3) . ? O11 C30 1.425(3) . ? O11 C31 1.426(2) . ? O13 C34 1.419(2) . ? O13 C35 1.422(3) . ? O8 C36 1.431(2) . ? O8 C25 1.433(2) . ? O1 C4 1.386(2) . ? O1 C7 1.399(2) . ? O4 C16 1.424(3) . ? O4 C17 1.429(3) . ? O6 C20 1.419(3) . ? O6 C21 1.427(3) . ? O2 C13 1.428(3) . ? O2 C24 1.429(3) . ? N1 C1 1.471(3) . ? N1 H1NB 0.89(3) . ? N1 H1NA 0.92(3) . ? N1 H1NC 0.88(3) . ? N2 C10 1.465(3) . ? N2 H2NA 0.91(3) . ? N2 H2NB 0.90(3) . ? N2 H2NC 0.93(3) . ? C4 C5 1.384(3) . ? C4 C3 1.386(3) . ? C1 C2 1.381(3) . ? C1 C6 1.385(3) . ? C8 C7 1.381(3) . ? C8 C9 1.389(3) . ? C8 H8 0.9500 . ? C5 C6 1.389(3) . ? C5 H5 0.9500 . ? C35 C36 1.503(3) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C10 C9 1.380(3) . ? C10 C11 1.385(3) . ? C25 C26 1.500(3) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C7 C12 1.381(3) . ? C2 C3 1.385(3) . ? C2 H2 0.9500 . ? C6 H6 0.9500 . ? C9 H9 0.9500 . ? C11 C12 1.384(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C3 H3 0.9500 . ? C22 C21 1.496(3) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C18 C17 1.495(3) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C29 C30 1.500(3) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C34 C33 1.498(3) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? C28 C27 1.496(3) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C31 C32 1.502(3) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C20 C19 1.492(3) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C16 C15 1.489(3) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C23 C24 1.492(3) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C14 C13 1.494(4) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? Cl1 O17 1.396(2) . ? Cl1 O14 1.4056(18) . ? Cl1 O15 1.413(2) . ? Cl1 O16 1.4191(19) . ? N3 C38 1.134(3) . ? C38 C37 1.457(4) . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? N4 C39 1.122(3) . ? C39 C40 1.466(4) . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 H40C 0.9800 . ? 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 O18 Cl2 O19 109.82(11) . . ? O18 Cl2 O20 109.51(12) . . ? O19 Cl2 O20 109.63(12) . . ? O18 Cl2 O21 108.85(11) . . ? O19 Cl2 O21 109.98(11) . . ? O20 Cl2 O21 109.03(11) . . ? C29 O10 C28 113.40(15) . . ? C33 O12 C32 111.85(15) . . ? C14 O3 C15 110.90(18) . . ? C27 O9 C26 111.71(16) . . ? C18 O5 C19 111.93(16) . . ? C23 O7 C22 111.90(16) . . ? C30 O11 C31 111.05(16) . . ? C34 O13 C35 111.56(16) . . ? C36 O8 C25 112.50(16) . . ? C4 O1 C7 117.23(15) . . ? C16 O4 C17 111.19(17) . . ? C20 O6 C21 113.61(17) . . ? C13 O2 C24 111.97(18) . . ? C1 N1 H1NB 107.0(15) . . ? C1 N1 H1NA 109.3(15) . . ? H1NB N1 H1NA 112(2) . . ? C1 N1 H1NC 113.2(17) . . ? H1NB N1 H1NC 107(2) . . ? H1NA N1 H1NC 108(2) . . ? C10 N2 H2NA 109.9(14) . . ? C10 N2 H2NB 113.6(16) . . ? H2NA N2 H2NB 104(2) . . ? C10 N2 H2NC 111.4(17) . . ? H2NA N2 H2NC 111(2) . . ? H2NB N2 H2NC 106(2) . . ? C5 C4 O1 122.66(18) . . ? C5 C4 C3 121.36(18) . . ? O1 C4 C3 115.88(17) . . ? C2 C1 C6 121.13(18) . . ? C2 C1 N1 120.05(18) . . ? C6 C1 N1 118.81(18) . . ? C7 C8 C9 119.25(19) . . ? C7 C8 H8 120.4 . . ? C9 C8 H8 120.4 . . ? C4 C5 C6 118.79(18) . . ? C4 C5 H5 120.6 . . ? C6 C5 H5 120.6 . . ? O13 C35 C36 109.83(17) . . ? O13 C35 H35A 109.7 . . ? C36 C35 H35A 109.7 . . ? O13 C35 H35B 109.7 . . ? C36 C35 H35B 109.7 . . ? H35A C35 H35B 108.2 . . ? C9 C10 C11 121.23(18) . . ? C9 C10 N2 119.31(18) . . ? C11 C10 N2 119.46(18) . . ? O8 C25 C26 108.04(17) . . ? O8 C25 H25A 110.1 . . ? C26 C25 H25A 110.1 . . ? O8 C25 H25B 110.1 . . ? C26 C25 H25B 110.1 . . ? H25A C25 H25B 108.4 . . ? C12 C7 C8 121.53(19) . . ? C12 C7 O1 119.60(18) . . ? C8 C7 O1 118.72(18) . . ? C1 C2 C3 119.26(18) . . ? C1 C2 H2 120.4 . . ? C3 C2 H2 120.4 . . ? C1 C6 C5 119.84(18) . . ? C1 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? C10 C9 C8 119.31(19) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? C12 C11 C10 119.49(19) . . ? C12 C11 H11 120.3 . . ? C10 C11 H11 120.3 . . ? C7 C12 C11 119.16(19) . . ? C7 C12 H12 120.4 . . ? C11 C12 H12 120.4 . . ? C2 C3 C4 119.57(18) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? O7 C22 C21 109.31(17) . . ? O7 C22 H22A 109.8 . . ? C21 C22 H22A 109.8 . . ? O7 C22 H22B 109.8 . . ? C21 C22 H22B 109.8 . . ? H22A C22 H22B 108.3 . . ? O5 C18 C17 109.03(17) . . ? O5 C18 H18A 109.9 . . ? C17 C18 H18A 109.9 . . ? O5 C18 H18B 109.9 . . ? C17 C18 H18B 109.9 . . ? H18A C18 H18B 108.3 . . ? O10 C29 C30 108.15(17) . . ? O10 C29 H29A 110.1 . . ? C30 C29 H29A 110.1 . . ? O10 C29 H29B 110.1 . . ? C30 C29 H29B 110.1 . . ? H29A C29 H29B 108.4 . . ? O13 C34 C33 108.85(16) . . ? O13 C34 H34A 109.9 . . ? C33 C34 H34A 109.9 . . ? O13 C34 H34B 109.9 . . ? C33 C34 H34B 109.9 . . ? H34A C34 H34B 108.3 . . ? O8 C36 C35 108.29(17) . . ? O8 C36 H36A 110.0 . . ? C35 C36 H36A 110.0 . . ? O8 C36 H36B 110.0 . . ? C35 C36 H36B 110.0 . . ? H36A C36 H36B 108.4 . . ? O10 C28 C27 108.63(16) . . ? O10 C28 H28A 110.0 . . ? C27 C28 H28A 110.0 . . ? O10 C28 H28B 110.0 . . ? C27 C28 H28B 110.0 . . ? H28A C28 H28B 108.3 . . ? O11 C31 C32 110.18(17) . . ? O11 C31 H31A 109.6 . . ? C32 C31 H31A 109.6 . . ? O11 C31 H31B 109.6 . . ? C32 C31 H31B 109.6 . . ? H31A C31 H31B 108.1 . . ? O6 C20 C19 107.80(18) . . ? O6 C20 H20A 110.1 . . ? C19 C20 H20A 110.1 . . ? O6 C20 H20B 110.1 . . ? C19 C20 H20B 110.1 . . ? H20A C20 H20B 108.5 . . ? O9 C27 C28 109.35(17) . . ? O9 C27 H27A 109.8 . . ? C28 C27 H27A 109.8 . . ? O9 C27 H27B 109.8 . . ? C28 C27 H27B 109.8 . . ? H27A C27 H27B 108.3 . . ? O12 C33 C34 108.61(16) . . ? O12 C33 H33A 110.0 . . ? C34 C33 H33A 110.0 . . ? O12 C33 H33B 110.0 . . ? C34 C33 H33B 110.0 . . ? H33A C33 H33B 108.3 . . ? O12 C32 C31 108.75(17) . . ? O12 C32 H32A 109.9 . . ? C31 C32 H32A 109.9 . . ? O12 C32 H32B 109.9 . . ? C31 C32 H32B 109.9 . . ? H32A C32 H32B 108.3 . . ? O4 C16 C15 108.49(18) . . ? O4 C16 H16A 110.0 . . ? C15 C16 H16A 110.0 . . ? O4 C16 H16B 110.0 . . ? C15 C16 H16B 110.0 . . ? H16A C16 H16B 108.4 . . ? O9 C26 C25 108.94(17) . . ? O9 C26 H26A 109.9 . . ? C25 C26 H26A 109.9 . . ? O9 C26 H26B 109.9 . . ? C25 C26 H26B 109.9 . . ? H26A C26 H26B 108.3 . . ? O6 C21 C22 108.55(18) . . ? O6 C21 H21A 110.0 . . ? C22 C21 H21A 110.0 . . ? O6 C21 H21B 110.0 . . ? C22 C21 H21B 110.0 . . ? H21A C21 H21B 108.4 . . ? O5 C19 C20 109.44(17) . . ? O5 C19 H19A 109.8 . . ? C20 C19 H19A 109.8 . . ? O5 C19 H19B 109.8 . . ? C20 C19 H19B 109.8 . . ? H19A C19 H19B 108.2 . . ? O4 C17 C18 108.48(18) . . ? O4 C17 H17A 110.0 . . ? C18 C17 H17A 110.0 . . ? O4 C17 H17B 110.0 . . ? C18 C17 H17B 110.0 . . ? H17A C17 H17B 108.4 . . ? O7 C23 C24 108.19(18) . . ? O7 C23 H23A 110.1 . . ? C24 C23 H23A 110.1 . . ? O7 C23 H23B 110.1 . . ? C24 C23 H23B 110.1 . . ? H23A C23 H23B 108.4 . . ? O11 C30 C29 109.53(18) . . ? O11 C30 H30A 109.8 . . ? C29 C30 H30A 109.8 . . ? O11 C30 H30B 109.8 . . ? C29 C30 H30B 109.8 . . ? H30A C30 H30B 108.2 . . ? O3 C15 C16 109.65(18) . . ? O3 C15 H15A 109.7 . . ? C16 C15 H15A 109.7 . . ? O3 C15 H15B 109.7 . . ? C16 C15 H15B 109.7 . . ? H15A C15 H15B 108.2 . . ? O2 C24 C23 109.19(19) . . ? O2 C24 H24A 109.8 . . ? C23 C24 H24A 109.8 . . ? O2 C24 H24B 109.8 . . ? C23 C24 H24B 109.8 . . ? H24A C24 H24B 108.3 . . ? O3 C14 C13 108.9(2) . . ? O3 C14 H14A 109.9 . . ? C13 C14 H14A 109.9 . . ? O3 C14 H14B 109.9 . . ? C13 C14 H14B 109.9 . . ? H14A C14 H14B 108.3 . . ? O2 C13 C14 108.8(2) . . ? O2 C13 H13A 109.9 . . ? C14 C13 H13A 109.9 . . ? O2 C13 H13B 109.9 . . ? C14 C13 H13B 109.9 . . ? H13A C13 H13B 108.3 . . ? O17 Cl1 O14 108.05(16) . . ? O17 Cl1 O15 112.0(2) . . ? O14 Cl1 O15 108.72(14) . . ? O17 Cl1 O16 109.40(18) . . ? O14 Cl1 O16 110.23(14) . . ? O15 Cl1 O16 108.46(14) . . ? N3 C38 C37 179.0(3) . . ? C38 C37 H37A 109.5 . . ? C38 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C38 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? N4 C39 C40 179.5(4) . . ? C39 C40 H40A 109.5 . . ? C39 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C39 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? 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 H1NC O3 0.88(3) 2.01(3) 2.893(2) 178(3) 1_545 N1 H1NB O5 0.89(3) 1.97(3) 2.827(2) 164(2) 1_545 N1 H1NA O7 0.92(3) 1.96(3) 2.873(2) 170(2) 1_545 N2 H2NA O8 0.91(3) 1.94(3) 2.839(2) 172(2) . N2 H2NC O10 0.93(3) 1.92(3) 2.848(2) 175(3) . N2 H2NB O12 0.90(3) 2.03(3) 2.925(2) 172(2) . C5 H5 O20 0.95 2.53 3.404(3) 153.0 . C29 H29A O18 0.99 2.50 3.335(3) 142.3 2_566 C33 H33A O16 0.99 2.35 3.237(3) 148.3 2_656 C16 H16A O14 0.99 2.62 3.575(3) 161.4 1_565 C17 H17A O21 0.99 2.58 3.517(3) 157.3 1_565 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.753 _refine_diff_density_min -0.594 _refine_diff_density_rms 0.054 #END************************************************************** data_DADPM-12C4 _database_code_depnum_ccdc_archive 'CCDC 846231' #TrackingRef '- Structures(3).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C13 H16 N2),2(C8 H16 O4),4(Cl O4),(H2 O)' _chemical_formula_sum 'C42 H66 Cl4 N4 O25' _chemical_formula_weight 1168.79 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 17.190(3) _cell_length_b 16.795(2) _cell_length_c 18.068(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.640(2) _cell_angle_gamma 90.00 _cell_volume 5210.7(13) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9527 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 25.02 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.490 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2456 _exptl_absorpt_coefficient_mu 0.317 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8577 _exptl_absorpt_correction_T_max 0.9393 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD 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 48928 _diffrn_reflns_av_R_equivalents 0.0394 _diffrn_reflns_av_sigmaI/netI 0.0281 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 25.00 _reflns_number_total 9128 _reflns_number_gt 8626 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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. ; _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^)+(0.0832P)^2^+15.1827P] 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 9128 _refine_ls_number_parameters 724 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0863 _refine_ls_R_factor_gt 0.0828 _refine_ls_wR_factor_ref 0.2006 _refine_ls_wR_factor_gt 0.1978 _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_restrained_S_all 1.106 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3417(3) 0.1785(3) 0.4293(2) 0.0400(10) Uani 1 1 d . . . H1 H 0.3103 0.1388 0.4052 0.048 Uiso 1 1 calc R . . C2 C 0.3333(3) 0.2573(3) 0.4074(2) 0.0376(10) Uani 1 1 d . . . H2 H 0.2968 0.2718 0.3686 0.045 Uiso 1 1 calc R . . C3 C 0.3787(2) 0.3140(2) 0.4431(2) 0.0323(9) Uani 1 1 d . . . C4 C 0.4306(3) 0.2941(3) 0.5005(2) 0.0362(10) Uani 1 1 d . . . H4 H 0.4607 0.3342 0.5255 0.043 Uiso 1 1 calc R . . C5 C 0.4383(2) 0.2156(3) 0.5212(2) 0.0344(9) Uani 1 1 d . . . H5 H 0.4741 0.2016 0.5607 0.041 Uiso 1 1 calc R . . C6 C 0.3947(2) 0.1565(2) 0.4854(2) 0.0319(9) Uani 1 1 d . . . C7 C 0.4066(3) 0.0707(3) 0.5091(2) 0.0418(11) Uani 1 1 d . . . H7A H 0.4603 0.0648 0.5306 0.050 Uiso 1 1 calc R . . H7B H 0.3706 0.0588 0.5488 0.050 Uiso 1 1 calc R . . C8 C 0.3941(2) 0.0096(2) 0.4486(2) 0.0300(8) Uani 1 1 d . . . C9 C 0.3501(2) -0.0578(2) 0.4604(2) 0.0324(9) Uani 1 1 d . . . H9 H 0.3284 -0.0654 0.5074 0.039 Uiso 1 1 calc R . . C10 C 0.3369(3) -0.1140(3) 0.4057(2) 0.0356(9) Uani 1 1 d . . . H10 H 0.3071 -0.1603 0.4150 0.043 Uiso 1 1 calc R . . C11 C 0.3675(2) -0.1023(2) 0.3373(2) 0.0274(8) Uani 1 1 d . . . C12 C 0.4138(2) -0.0373(2) 0.3241(2) 0.0285(8) Uani 1 1 d . . . H12 H 0.4363 -0.0305 0.2775 0.034 Uiso 1 1 calc R . . C13 C 0.4268(3) 0.0177(2) 0.3801(2) 0.0354(9) Uani 1 1 d . . . H13 H 0.4590 0.0624 0.3715 0.043 Uiso 1 1 calc R . . C14 C 0.0711(3) 0.7355(3) 0.0776(2) 0.0397(10) Uani 1 1 d . . . H14 H 0.0335 0.7124 0.1081 0.048 Uiso 1 1 calc R . . C15 C 0.1004(3) 0.8103(3) 0.0953(2) 0.0389(10) Uani 1 1 d . . . H15 H 0.0832 0.8384 0.1371 0.047 Uiso 1 1 calc R . . C16 C 0.1552(2) 0.8432(2) 0.0508(2) 0.0300(9) Uani 1 1 d . . . C17 C 0.1803(2) 0.8034(3) -0.0092(2) 0.0366(10) Uani 1 1 d . . . H17 H 0.2178 0.8268 -0.0395 0.044 Uiso 1 1 calc R . . C18 C 0.1507(2) 0.7284(2) -0.0257(2) 0.0340(9) Uani 1 1 d . . . H18 H 0.1689 0.7003 -0.0672 0.041 Uiso 1 1 calc R . . C19 C 0.0951(3) 0.6935(2) 0.0168(2) 0.0323(9) Uani 1 1 d . . . C20 C 0.0601(3) 0.6133(2) -0.0037(2) 0.0366(10) Uani 1 1 d . . . H20A H 0.0729 0.6002 -0.0551 0.044 Uiso 1 1 calc R . . H20B H 0.0027 0.6169 -0.0022 0.044 Uiso 1 1 calc R . . C21 C 0.0888(2) 0.5465(2) 0.0472(2) 0.0295(8) Uani 1 1 d . . . C22 C 0.1554(3) 0.5038(3) 0.0319(2) 0.0360(9) Uani 1 1 d . . . H22 H 0.1832 0.5168 -0.0107 0.043 Uiso 1 1 calc R . . C23 C 0.1818(3) 0.4426(2) 0.0778(2) 0.0350(9) Uani 1 1 d . . . H23 H 0.2273 0.4137 0.0667 0.042 Uiso 1 1 calc R . . C24 C 0.1417(2) 0.4241(2) 0.1394(2) 0.0275(8) Uani 1 1 d . . . C25 C 0.0752(2) 0.4650(2) 0.1563(2) 0.0317(9) Uani 1 1 d . . . H25 H 0.0478 0.4519 0.1991 0.038 Uiso 1 1 calc R . . C26 C 0.0492(2) 0.5256(2) 0.1093(2) 0.0330(9) Uani 1 1 d . . . H26 H 0.0030 0.5536 0.1201 0.040 Uiso 1 1 calc R . . C27 C 0.1333(3) 0.2337(3) 0.0243(2) 0.0481(12) Uani 1 1 d . . . H27A H 0.1564 0.2803 -0.0002 0.058 Uiso 1 1 calc R . . H27B H 0.1043 0.2024 -0.0143 0.058 Uiso 1 1 calc R . . C28 C 0.1964(3) 0.1843(3) 0.0574(3) 0.0554(13) Uani 1 1 d . . . H28A H 0.1748 0.1379 0.0832 0.066 Uiso 1 1 calc R . . H28B H 0.2306 0.1647 0.0187 0.066 Uiso 1 1 calc R . . C29 C 0.2904(3) 0.1877(3) 0.1608(3) 0.0484(12) Uani 1 1 d . . . H29A H 0.3166 0.1446 0.1341 0.058 Uiso 1 1 calc R . . H29B H 0.3312 0.2241 0.1815 0.058 Uiso 1 1 calc R . . C30 C 0.2486(3) 0.1532(3) 0.2215(3) 0.0585(14) Uani 1 1 d . . . H30A H 0.2066 0.1176 0.2019 0.070 Uiso 1 1 calc R . . H30B H 0.2845 0.1219 0.2545 0.070 Uiso 1 1 calc R . . C31 C 0.1507(4) 0.1919(3) 0.3086(2) 0.0518(13) Uani 1 1 d . . . H31A H 0.1660 0.1439 0.3375 0.062 Uiso 1 1 calc R . . H31B H 0.1412 0.2354 0.3440 0.062 Uiso 1 1 calc R . . C32 C 0.0790(4) 0.1755(3) 0.2651(3) 0.0650(16) Uani 1 1 d . . . H32A H 0.0885 0.1352 0.2266 0.078 Uiso 1 1 calc R . . H32B H 0.0387 0.1547 0.2975 0.078 Uiso 1 1 calc R . . C33 C -0.0059(3) 0.2324(3) 0.1693(3) 0.0499(12) Uani 1 1 d . . . H33A H -0.0449 0.1933 0.1850 0.060 Uiso 1 1 calc R . . H33B H -0.0334 0.2830 0.1576 0.060 Uiso 1 1 calc R . . C34 C 0.0302(3) 0.2028(3) 0.1022(3) 0.0576(14) Uani 1 1 d . . . H34A H 0.0604 0.1538 0.1136 0.069 Uiso 1 1 calc R . . H34B H -0.0104 0.1904 0.0633 0.069 Uiso 1 1 calc R . . C35 C 0.3391(3) 0.7360(3) 0.1077(2) 0.0382(10) Uani 1 1 d . . . H35A H 0.3470 0.7890 0.0853 0.046 Uiso 1 1 calc R . . H35B H 0.3165 0.7006 0.0685 0.046 Uiso 1 1 calc R . . C36 C 0.4154(3) 0.7037(3) 0.1343(2) 0.0378(10) Uani 1 1 d . . . H36A H 0.4085 0.6504 0.1566 0.045 Uiso 1 1 calc R . . H36B H 0.4502 0.6983 0.0925 0.045 Uiso 1 1 calc R . . C37 C 0.5132(3) 0.7243(3) 0.2317(3) 0.0463(11) Uani 1 1 d . . . H37A H 0.5427 0.7684 0.2561 0.056 Uiso 1 1 calc R . . H37B H 0.5485 0.6968 0.1983 0.056 Uiso 1 1 calc R . . C38 C 0.4888(3) 0.6673(3) 0.2891(3) 0.0431(11) Uani 1 1 d . . . H38A H 0.4593 0.6226 0.2658 0.052 Uiso 1 1 calc R . . H38B H 0.5351 0.6454 0.3168 0.052 Uiso 1 1 calc R . . C39 C 0.3941(3) 0.6587(3) 0.3802(2) 0.0426(11) Uani 1 1 d . . . H39A H 0.3783 0.6877 0.4248 0.051 Uiso 1 1 calc R . . H39B H 0.4253 0.6120 0.3970 0.051 Uiso 1 1 calc R . . C40 C 0.3234(3) 0.6305(2) 0.3383(2) 0.0372(10) Uani 1 1 d . . . H40A H 0.3382 0.6015 0.2934 0.045 Uiso 1 1 calc R . . H40B H 0.2939 0.5937 0.3694 0.045 Uiso 1 1 calc R . . C41 C 0.2173(3) 0.6792(3) 0.2605(3) 0.0448(11) Uani 1 1 d . . . H41A H 0.1778 0.7221 0.2588 0.054 Uiso 1 1 calc R . . H41B H 0.1910 0.6291 0.2737 0.054 Uiso 1 1 calc R . . C42 C 0.2489(3) 0.6702(3) 0.1853(3) 0.0406(10) Uani 1 1 d . . . H42A H 0.2877 0.6267 0.1856 0.049 Uiso 1 1 calc R . . H42B H 0.2062 0.6570 0.1487 0.049 Uiso 1 1 calc R . . Cl1 Cl 0.39516(5) 0.96463(5) 0.08017(5) 0.0279(2) Uani 1 1 d . . . Cl2 Cl 0.36823(6) 0.43516(5) 0.22559(5) 0.0302(2) Uani 1 1 d . . . Cl3 Cl 0.84383(7) 0.44071(6) 0.21648(6) 0.0405(3) Uani 1 1 d . . . Cl4 Cl 0.14552(7) 0.04018(6) 0.89211(6) 0.0380(3) Uani 1 1 d . . . H1NA H 0.373(3) 0.429(4) 0.454(4) 0.062(18) Uiso 1 1 d . . . H2NA H 0.388(3) -0.164(2) 0.260(2) 0.019(11) Uiso 1 1 d . . . H3NA H 0.143(2) 0.946(2) 0.0776(19) 0.006(9) Uiso 1 1 d . . . H4NA H 0.202(3) 0.375(3) 0.219(3) 0.032(12) Uiso 1 1 d . . . H1NB H 0.408(3) 0.409(3) 0.384(3) 0.058(16) Uiso 1 1 d . . . H2NB H 0.330(3) -0.197(3) 0.297(3) 0.038(13) Uiso 1 1 d . . . H3NB H 0.210(4) 0.919(4) 0.107(4) 0.07(2) Uiso 1 1 d . . . H4NB H 0.193(3) 0.322(3) 0.163(3) 0.043(14) Uiso 1 1 d . . . H1NC H 0.322(4) 0.408(4) 0.405(4) 0.08(2) Uiso 1 1 d . . . H2NC H 0.311(3) -0.134(3) 0.250(3) 0.042(14) Uiso 1 1 d . . . H3NC H 0.211(5) 0.946(5) 0.036(5) 0.10(3) Uiso 1 1 d . . . H4NC H 0.133(3) 0.338(3) 0.204(3) 0.031(13) Uiso 1 1 d . . . N1 N 0.3730(3) 0.3976(2) 0.4188(2) 0.0409(9) Uani 1 1 d . . . N2 N 0.3461(3) -0.1567(2) 0.2772(2) 0.0334(8) Uani 1 1 d . . . N3 N 0.1853(3) 0.9233(2) 0.0673(3) 0.0371(9) Uani 1 1 d . . . N4 N 0.1691(3) 0.3586(2) 0.1872(2) 0.0312(8) Uani 1 1 d . . . O1 O 0.0786(2) 0.2621(2) 0.0784(2) 0.0576(10) Uani 1 1 d . . . O2 O 0.2380(2) 0.2327(2) 0.10722(19) 0.0500(8) Uani 1 1 d . . . O3 O 0.2178(2) 0.21584(19) 0.2595(2) 0.0563(10) Uani 1 1 d . . . O4 O 0.0540(2) 0.24624(19) 0.2324(2) 0.0630(11) Uani 1 1 d . . . O5 O 0.28445(18) 0.74341(16) 0.16596(16) 0.0371(7) Uani 1 1 d . . . O6 O 0.44839(18) 0.75702(17) 0.18808(16) 0.0378(7) Uani 1 1 d . . . O7 O 0.44123(17) 0.70962(17) 0.33787(16) 0.0370(7) Uani 1 1 d . . . O8 O 0.27623(16) 0.69778(16) 0.31779(16) 0.0337(6) Uani 1 1 d . . . O9 O 0.4252(4) 1.0411(3) 0.0840(4) 0.115(2) Uani 1 1 d . . . O10 O 0.4564(2) 0.9083(3) 0.0725(3) 0.0839(14) Uani 1 1 d . . . O11 O 0.3500(2) 0.9446(2) 0.14011(18) 0.0591(10) Uani 1 1 d . . . O12 O 0.3471(3) 0.9583(4) 0.0149(2) 0.102(2) Uani 1 1 d . . . O13 O 0.3764(2) 0.50635(18) 0.18497(18) 0.0516(9) Uani 1 1 d . . . O14 O 0.4332(2) 0.4242(3) 0.27698(19) 0.0618(10) Uani 1 1 d . . . O15 O 0.3608(2) 0.36964(18) 0.17576(17) 0.0504(9) Uani 1 1 d . . . O16 O 0.29911(19) 0.4388(2) 0.26819(18) 0.0479(8) Uani 1 1 d . . . O17 O 0.8297(4) 0.4958(2) 0.1594(2) 0.0999(19) Uani 1 1 d . . . O18 O 0.9187(3) 0.4508(5) 0.2488(3) 0.130(3) Uani 1 1 d . . . O19 O 0.8381(3) 0.3625(2) 0.1868(2) 0.0641(11) Uani 1 1 d . . . O20 O 0.78803(18) 0.44947(19) 0.27193(16) 0.0412(7) Uani 1 1 d . . . O21 O 0.1587(4) 0.1152(3) 0.8623(3) 0.103(2) Uani 1 1 d . . . O22 O 0.2158(2) 0.0135(3) 0.9285(2) 0.0696(12) Uani 1 1 d . . . O23 O 0.1228(3) -0.0154(3) 0.8358(3) 0.0919(16) Uani 1 1 d . . . O24 O 0.0877(2) 0.0436(3) 0.9470(2) 0.0705(12) Uani 1 1 d . . . O25 O 0.0631(2) 0.0072(2) 0.1134(3) 0.0681(11) 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 C1 0.048(3) 0.039(2) 0.032(2) -0.0100(19) -0.0076(19) -0.001(2) C2 0.043(2) 0.042(2) 0.027(2) -0.0052(18) -0.0075(18) 0.0065(19) C3 0.037(2) 0.033(2) 0.027(2) -0.0052(17) 0.0102(17) 0.0066(17) C4 0.040(2) 0.036(2) 0.032(2) -0.0120(18) 0.0011(18) -0.0023(18) C5 0.036(2) 0.044(2) 0.0234(19) -0.0075(17) -0.0032(16) 0.0032(18) C6 0.040(2) 0.035(2) 0.0214(18) -0.0084(16) 0.0028(16) 0.0032(18) C7 0.061(3) 0.037(2) 0.027(2) -0.0056(18) -0.006(2) 0.003(2) C8 0.035(2) 0.032(2) 0.0230(19) -0.0022(16) 0.0016(16) 0.0031(17) C9 0.037(2) 0.039(2) 0.0217(19) 0.0018(16) 0.0070(16) -0.0004(18) C10 0.041(2) 0.035(2) 0.031(2) 0.0044(17) 0.0041(18) -0.0086(18) C11 0.035(2) 0.0238(19) 0.0234(18) -0.0003(15) -0.0020(15) 0.0030(16) C12 0.030(2) 0.032(2) 0.0233(19) 0.0009(16) 0.0094(15) -0.0007(16) C13 0.042(2) 0.031(2) 0.034(2) -0.0008(17) 0.0069(18) -0.0117(18) C14 0.060(3) 0.030(2) 0.029(2) 0.0063(17) 0.002(2) -0.010(2) C15 0.064(3) 0.028(2) 0.024(2) -0.0006(16) -0.0035(19) -0.003(2) C16 0.032(2) 0.026(2) 0.030(2) 0.0027(16) -0.0104(16) -0.0032(16) C17 0.031(2) 0.038(2) 0.040(2) -0.0027(19) -0.0035(18) -0.0028(18) C18 0.035(2) 0.034(2) 0.032(2) -0.0047(17) -0.0068(17) 0.0062(17) C19 0.045(2) 0.0226(19) 0.028(2) 0.0009(16) -0.0122(17) 0.0002(17) C20 0.050(3) 0.027(2) 0.031(2) -0.0008(17) -0.0112(19) -0.0043(18) C21 0.037(2) 0.0213(19) 0.030(2) -0.0028(15) -0.0046(16) -0.0068(16) C22 0.040(2) 0.040(2) 0.029(2) 0.0016(18) 0.0079(18) -0.0053(19) C23 0.036(2) 0.033(2) 0.037(2) 0.0041(18) 0.0075(18) 0.0028(17) C24 0.036(2) 0.0219(18) 0.0251(19) -0.0003(15) 0.0004(16) -0.0065(15) C25 0.039(2) 0.028(2) 0.029(2) -0.0048(16) 0.0099(17) -0.0078(17) C26 0.039(2) 0.0225(19) 0.038(2) -0.0101(17) 0.0059(18) -0.0006(17) C27 0.064(3) 0.052(3) 0.029(2) -0.008(2) 0.003(2) 0.001(2) C28 0.055(3) 0.063(3) 0.049(3) -0.017(3) 0.009(2) -0.003(3) C29 0.026(2) 0.038(2) 0.081(4) -0.005(2) -0.002(2) 0.0073(18) C30 0.065(3) 0.050(3) 0.059(3) 0.001(3) -0.012(3) 0.008(3) C31 0.097(4) 0.032(2) 0.026(2) 0.0059(18) 0.003(2) -0.006(2) C32 0.082(4) 0.051(3) 0.066(4) 0.004(3) 0.039(3) -0.007(3) C33 0.031(2) 0.041(3) 0.078(4) -0.004(2) 0.005(2) 0.000(2) C34 0.044(3) 0.047(3) 0.081(4) -0.003(3) -0.011(3) 0.002(2) C35 0.064(3) 0.031(2) 0.0195(19) -0.0002(16) -0.0030(18) 0.006(2) C36 0.047(3) 0.036(2) 0.031(2) -0.0013(18) 0.0073(19) 0.0020(19) C37 0.028(2) 0.052(3) 0.058(3) 0.003(2) -0.001(2) -0.004(2) C38 0.030(2) 0.054(3) 0.044(3) 0.002(2) -0.0072(19) 0.003(2) C39 0.057(3) 0.040(2) 0.030(2) 0.0063(19) -0.004(2) 0.002(2) C40 0.046(3) 0.028(2) 0.039(2) 0.0033(18) 0.0098(19) 0.0015(18) C41 0.027(2) 0.042(3) 0.065(3) -0.009(2) 0.005(2) -0.0038(19) C42 0.034(2) 0.042(2) 0.045(3) -0.010(2) -0.0125(19) 0.0006(19) Cl1 0.0310(5) 0.0292(5) 0.0236(4) 0.0049(4) 0.0001(4) -0.0051(4) Cl2 0.0429(6) 0.0234(5) 0.0252(5) -0.0023(4) 0.0099(4) -0.0041(4) Cl3 0.0527(7) 0.0371(6) 0.0330(5) -0.0029(4) 0.0152(5) -0.0126(5) Cl4 0.0470(6) 0.0359(6) 0.0317(5) 0.0016(4) 0.0081(4) 0.0104(4) N1 0.052(3) 0.037(2) 0.035(2) -0.0033(18) 0.0134(19) 0.0041(18) N2 0.050(3) 0.0213(19) 0.0285(19) 0.0003(15) 0.0004(19) -0.0002(18) N3 0.039(2) 0.033(2) 0.039(2) -0.0041(17) -0.0045(19) -0.0032(18) N4 0.037(2) 0.0251(18) 0.0310(19) 0.0014(15) -0.0009(17) -0.0056(17) O1 0.054(2) 0.0378(19) 0.079(3) -0.0023(17) -0.0218(19) 0.0018(16) O2 0.052(2) 0.0468(19) 0.053(2) -0.0051(16) 0.0220(16) -0.0075(16) O3 0.084(3) 0.0276(16) 0.055(2) 0.0019(15) -0.0269(19) -0.0015(16) O4 0.074(3) 0.0288(17) 0.090(3) -0.0097(18) 0.048(2) -0.0069(16) O5 0.0473(18) 0.0280(15) 0.0348(15) -0.0044(12) -0.0111(13) 0.0080(13) O6 0.0470(18) 0.0306(15) 0.0360(16) 0.0017(12) 0.0045(13) -0.0069(13) O7 0.0403(16) 0.0367(16) 0.0334(15) -0.0008(13) -0.0058(13) -0.0066(13) O8 0.0360(15) 0.0268(14) 0.0388(16) -0.0031(12) 0.0064(12) 0.0004(12) O9 0.138(5) 0.051(3) 0.159(6) -0.014(3) 0.045(4) -0.038(3) O10 0.060(3) 0.089(3) 0.105(4) 0.010(3) 0.026(2) 0.023(2) O11 0.063(2) 0.080(3) 0.0348(18) 0.0171(17) 0.0146(16) 0.0025(19) O12 0.064(3) 0.204(6) 0.038(2) 0.002(3) -0.005(2) -0.025(3) O13 0.085(3) 0.0260(16) 0.0461(19) 0.0024(14) 0.0244(18) 0.0005(16) O14 0.0400(19) 0.104(3) 0.0416(19) 0.005(2) 0.0048(15) -0.0091(19) O15 0.088(3) 0.0303(16) 0.0341(16) 0.0001(13) 0.0133(17) 0.0001(16) O16 0.0421(18) 0.064(2) 0.0385(17) -0.0075(15) 0.0115(14) -0.0120(16) O17 0.215(6) 0.041(2) 0.047(2) 0.0039(18) 0.046(3) -0.010(3) O18 0.065(3) 0.225(8) 0.102(4) -0.036(4) 0.023(3) -0.070(4) O19 0.097(3) 0.039(2) 0.058(2) -0.0100(17) 0.023(2) 0.0130(19) O20 0.0466(18) 0.0468(18) 0.0307(15) -0.0011(13) 0.0086(13) 0.0007(14) O21 0.188(6) 0.049(2) 0.076(3) 0.020(2) 0.065(3) 0.036(3) O22 0.073(3) 0.091(3) 0.045(2) 0.019(2) 0.0101(19) 0.019(2) O23 0.080(3) 0.121(4) 0.074(3) -0.047(3) 0.001(2) 0.007(3) O24 0.058(2) 0.087(3) 0.068(3) -0.015(2) 0.026(2) 0.001(2) O25 0.069(3) 0.047(2) 0.089(3) -0.003(2) 0.012(2) 0.0047(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.383(6) . ? C1 C2 1.387(6) . ? C1 H1 0.9500 . ? C2 C3 1.373(6) . ? C2 H2 0.9500 . ? C3 C4 1.378(6) . ? C3 N1 1.473(6) . ? C4 C5 1.376(6) . ? C4 H4 0.9500 . ? C5 C6 1.386(6) . ? C5 H5 0.9500 . ? C6 C7 1.515(6) . ? C7 C8 1.508(6) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.383(6) . ? C8 C13 1.389(6) . ? C9 C10 1.378(6) . ? C9 H9 0.9500 . ? C10 C11 1.379(6) . ? C10 H10 0.9500 . ? C11 C12 1.379(5) . ? C11 N2 1.454(5) . ? C12 C13 1.380(6) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C19 1.385(6) . ? C14 C15 1.385(6) . ? C14 H14 0.9500 . ? C15 C16 1.380(6) . ? C15 H15 0.9500 . ? C16 C17 1.360(6) . ? C16 N3 1.469(5) . ? C17 C18 1.386(6) . ? C17 H17 0.9500 . ? C18 C19 1.383(6) . ? C18 H18 0.9500 . ? C19 C20 1.514(5) . ? C20 C21 1.519(6) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C26 1.384(6) . ? C21 C22 1.389(6) . ? C22 C23 1.383(6) . ? C22 H22 0.9500 . ? C23 C24 1.373(6) . ? C23 H23 0.9500 . ? C24 C25 1.380(6) . ? C24 N4 1.462(5) . ? C25 C26 1.386(6) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 O1 1.467(6) . ? C27 C28 1.471(7) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 O2 1.386(6) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 C30 1.459(8) . ? C29 O2 1.497(6) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 O3 1.377(6) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 C32 1.457(9) . ? C31 O3 1.540(7) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 O4 1.386(7) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.473(8) . ? C33 O4 1.520(7) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 O1 1.379(7) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 O5 1.448(5) . ? C35 C36 1.479(6) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 O6 1.420(5) . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? C37 O6 1.443(5) . ? C37 C38 1.487(7) . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? C38 O7 1.420(6) . ? C38 H38A 0.9900 . ? C38 H38B 0.9900 . ? C39 O7 1.425(5) . ? C39 C40 1.478(6) . ? C39 H39A 0.9900 . ? C39 H39B 0.9900 . ? C40 O8 1.430(5) . ? C40 H40A 0.9900 . ? C40 H40B 0.9900 . ? C41 O8 1.448(5) . ? C41 C42 1.494(7) . ? C41 H41A 0.9900 . ? C41 H41B 0.9900 . ? C42 O5 1.423(5) . ? C42 H42A 0.9900 . ? C42 H42B 0.9900 . ? Cl1 O9 1.384(4) . ? Cl1 O11 1.402(3) . ? Cl1 O12 1.412(4) . ? Cl1 O10 1.426(4) . ? Cl2 O13 1.413(3) . ? Cl2 O15 1.424(3) . ? Cl2 O14 1.431(4) . ? Cl2 O16 1.446(3) . ? Cl3 O18 1.398(5) . ? Cl3 O17 1.398(4) . ? Cl3 O19 1.420(4) . ? Cl3 O20 1.426(3) . ? Cl4 O21 1.393(4) . ? Cl4 O22 1.421(4) . ? Cl4 O23 1.422(5) . ? Cl4 O24 1.438(4) . ? N1 H1NA 0.83(7) . ? N1 H1NB 0.90(6) . ? N1 H1NC 0.91(7) . ? N2 H2NA 0.81(4) . ? N2 H2NB 0.81(5) . ? N2 H2NC 0.86(5) . ? N3 H3NA 0.84(4) . ? N3 H3NB 0.81(7) . ? N3 H3NC 0.83(8) . ? N4 H4NA 0.84(5) . ? N4 H4NB 0.86(6) . ? N4 H4NC 0.78(5) . ? 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 C1 C2 121.4(4) . . ? C6 C1 H1 119.3 . . ? C2 C1 H1 119.3 . . ? C3 C2 C1 118.6(4) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? C2 C3 C4 121.4(4) . . ? C2 C3 N1 119.5(4) . . ? C4 C3 N1 119.1(4) . . ? C5 C4 C3 119.2(4) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C4 C5 C6 121.1(4) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C1 C6 C5 118.4(4) . . ? C1 C6 C7 122.5(4) . . ? C5 C6 C7 119.1(4) . . ? C8 C7 C6 115.4(3) . . ? C8 C7 H7A 108.4 . . ? C6 C7 H7A 108.4 . . ? C8 C7 H7B 108.4 . . ? C6 C7 H7B 108.4 . . ? H7A C7 H7B 107.5 . . ? C9 C8 C13 117.7(4) . . ? C9 C8 C7 120.3(4) . . ? C13 C8 C7 122.0(4) . . ? C10 C9 C8 121.4(4) . . ? C10 C9 H9 119.3 . . ? C8 C9 H9 119.3 . . ? C9 C10 C11 119.3(4) . . ? C9 C10 H10 120.4 . . ? C11 C10 H10 120.4 . . ? C12 C11 C10 121.0(4) . . ? C12 C11 N2 119.7(4) . . ? C10 C11 N2 119.2(4) . . ? C11 C12 C13 118.6(3) . . ? C11 C12 H12 120.7 . . ? C13 C12 H12 120.7 . . ? C12 C13 C8 121.9(4) . . ? C12 C13 H13 119.0 . . ? C8 C13 H13 119.0 . . ? C19 C14 C15 121.7(4) . . ? C19 C14 H14 119.2 . . ? C15 C14 H14 119.2 . . ? C16 C15 C14 118.7(4) . . ? C16 C15 H15 120.7 . . ? C14 C15 H15 120.7 . . ? C17 C16 C15 121.1(4) . . ? C17 C16 N3 119.4(4) . . ? C15 C16 N3 119.5(4) . . ? C16 C17 C18 119.4(4) . . ? C16 C17 H17 120.3 . . ? C18 C17 H17 120.3 . . ? C19 C18 C17 121.4(4) . . ? C19 C18 H18 119.3 . . ? C17 C18 H18 119.3 . . ? C18 C19 C14 117.7(4) . . ? C18 C19 C20 121.1(4) . . ? C14 C19 C20 121.2(4) . . ? C19 C20 C21 113.3(3) . . ? C19 C20 H20A 108.9 . . ? C21 C20 H20A 108.9 . . ? C19 C20 H20B 108.9 . . ? C21 C20 H20B 108.9 . . ? H20A C20 H20B 107.7 . . ? C26 C21 C22 118.1(4) . . ? C26 C21 C20 121.3(4) . . ? C22 C21 C20 120.6(4) . . ? C23 C22 C21 121.0(4) . . ? C23 C22 H22 119.5 . . ? C21 C22 H22 119.5 . . ? C24 C23 C22 119.4(4) . . ? C24 C23 H23 120.3 . . ? C22 C23 H23 120.3 . . ? C23 C24 C25 121.2(4) . . ? C23 C24 N4 119.3(4) . . ? C25 C24 N4 119.5(4) . . ? C24 C25 C26 118.6(4) . . ? C24 C25 H25 120.7 . . ? C26 C25 H25 120.7 . . ? C21 C26 C25 121.7(4) . . ? C21 C26 H26 119.2 . . ? C25 C26 H26 119.2 . . ? O1 C27 C28 113.3(4) . . ? O1 C27 H27A 108.9 . . ? C28 C27 H27A 108.9 . . ? O1 C27 H27B 108.9 . . ? C28 C27 H27B 108.9 . . ? H27A C27 H27B 107.7 . . ? O2 C28 C27 106.4(4) . . ? O2 C28 H28A 110.5 . . ? C27 C28 H28A 110.5 . . ? O2 C28 H28B 110.5 . . ? C27 C28 H28B 110.5 . . ? H28A C28 H28B 108.6 . . ? C30 C29 O2 112.6(4) . . ? C30 C29 H29A 109.1 . . ? O2 C29 H29A 109.1 . . ? C30 C29 H29B 109.1 . . ? O2 C29 H29B 109.1 . . ? H29A C29 H29B 107.8 . . ? O3 C30 C29 106.6(4) . . ? O3 C30 H30A 110.4 . . ? C29 C30 H30A 110.4 . . ? O3 C30 H30B 110.4 . . ? C29 C30 H30B 110.4 . . ? H30A C30 H30B 108.6 . . ? C32 C31 O3 112.2(4) . . ? C32 C31 H31A 109.2 . . ? O3 C31 H31A 109.2 . . ? C32 C31 H31B 109.2 . . ? O3 C31 H31B 109.2 . . ? H31A C31 H31B 107.9 . . ? O4 C32 C31 107.8(5) . . ? O4 C32 H32A 110.2 . . ? C31 C32 H32A 110.2 . . ? O4 C32 H32B 110.2 . . ? C31 C32 H32B 110.2 . . ? H32A C32 H32B 108.5 . . ? C34 C33 O4 111.9(4) . . ? C34 C33 H33A 109.2 . . ? O4 C33 H33A 109.2 . . ? C34 C33 H33B 109.2 . . ? O4 C33 H33B 109.2 . . ? H33A C33 H33B 107.9 . . ? O1 C34 C33 107.3(4) . . ? O1 C34 H34A 110.3 . . ? C33 C34 H34A 110.3 . . ? O1 C34 H34B 110.3 . . ? C33 C34 H34B 110.3 . . ? H34A C34 H34B 108.5 . . ? O5 C35 C36 112.9(3) . . ? O5 C35 H35A 109.0 . . ? C36 C35 H35A 109.0 . . ? O5 C35 H35B 109.0 . . ? C36 C35 H35B 109.0 . . ? H35A C35 H35B 107.8 . . ? O6 C36 C35 108.1(3) . . ? O6 C36 H36A 110.1 . . ? C35 C36 H36A 110.1 . . ? O6 C36 H36B 110.1 . . ? C35 C36 H36B 110.1 . . ? H36A C36 H36B 108.4 . . ? O6 C37 C38 113.1(4) . . ? O6 C37 H37A 109.0 . . ? C38 C37 H37A 109.0 . . ? O6 C37 H37B 109.0 . . ? C38 C37 H37B 109.0 . . ? H37A C37 H37B 107.8 . . ? O7 C38 C37 107.4(4) . . ? O7 C38 H38A 110.2 . . ? C37 C38 H38A 110.2 . . ? O7 C38 H38B 110.2 . . ? C37 C38 H38B 110.2 . . ? H38A C38 H38B 108.5 . . ? O7 C39 C40 113.1(3) . . ? O7 C39 H39A 109.0 . . ? C40 C39 H39A 109.0 . . ? O7 C39 H39B 109.0 . . ? C40 C39 H39B 109.0 . . ? H39A C39 H39B 107.8 . . ? O8 C40 C39 108.8(3) . . ? O8 C40 H40A 109.9 . . ? C39 C40 H40A 109.9 . . ? O8 C40 H40B 109.9 . . ? C39 C40 H40B 109.9 . . ? H40A C40 H40B 108.3 . . ? O8 C41 C42 113.7(3) . . ? O8 C41 H41A 108.8 . . ? C42 C41 H41A 108.8 . . ? O8 C41 H41B 108.8 . . ? C42 C41 H41B 108.8 . . ? H41A C41 H41B 107.7 . . ? O5 C42 C41 108.3(4) . . ? O5 C42 H42A 110.0 . . ? C41 C42 H42A 110.0 . . ? O5 C42 H42B 110.0 . . ? C41 C42 H42B 110.0 . . ? H42A C42 H42B 108.4 . . ? O9 Cl1 O11 113.7(3) . . ? O9 Cl1 O12 108.3(4) . . ? O11 Cl1 O12 107.7(3) . . ? O9 Cl1 O10 110.1(3) . . ? O11 Cl1 O10 110.6(3) . . ? O12 Cl1 O10 106.0(3) . . ? O13 Cl2 O15 109.49(19) . . ? O13 Cl2 O14 110.7(2) . . ? O15 Cl2 O14 110.8(2) . . ? O13 Cl2 O16 110.1(2) . . ? O15 Cl2 O16 108.5(2) . . ? O14 Cl2 O16 107.2(2) . . ? O18 Cl3 O17 110.7(4) . . ? O18 Cl3 O19 108.4(4) . . ? O17 Cl3 O19 109.1(2) . . ? O18 Cl3 O20 109.3(3) . . ? O17 Cl3 O20 110.5(3) . . ? O19 Cl3 O20 108.9(2) . . ? O21 Cl4 O22 108.3(3) . . ? O21 Cl4 O23 111.2(3) . . ? O22 Cl4 O23 108.9(3) . . ? O21 Cl4 O24 111.2(3) . . ? O22 Cl4 O24 107.1(2) . . ? O23 Cl4 O24 110.1(3) . . ? C3 N1 H1NA 112(4) . . ? C3 N1 H1NB 112(4) . . ? H1NA N1 H1NB 115(5) . . ? C3 N1 H1NC 108(4) . . ? H1NA N1 H1NC 93(5) . . ? H1NB N1 H1NC 115(5) . . ? C11 N2 H2NA 101(3) . . ? C11 N2 H2NB 106(3) . . ? H2NA N2 H2NB 113(5) . . ? C11 N2 H2NC 107(3) . . ? H2NA N2 H2NC 118(4) . . ? H2NB N2 H2NC 112(5) . . ? C16 N3 H3NA 99(2) . . ? C16 N3 H3NB 105(5) . . ? H3NA N3 H3NB 105(5) . . ? C16 N3 H3NC 119(5) . . ? H3NA N3 H3NC 116(6) . . ? H3NB N3 H3NC 112(7) . . ? C24 N4 H4NA 110(3) . . ? C24 N4 H4NB 112(3) . . ? H4NA N4 H4NB 106(4) . . ? C24 N4 H4NC 109(3) . . ? H4NA N4 H4NC 114(5) . . ? H4NB N4 H4NC 106(5) . . ? C34 O1 C27 112.9(4) . . ? C28 O2 C29 113.6(4) . . ? C30 O3 C31 113.8(4) . . ? C32 O4 C33 112.0(4) . . ? C42 O5 C35 113.8(3) . . ? C36 O6 C37 114.0(3) . . ? C38 O7 C39 113.0(3) . . ? C40 O8 C41 112.7(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 C41 H41B O23 0.99 2.53 3.502(7) 167.2 4_565 C36 H36A O13 0.99 2.54 3.511(5) 166.9 . C38 H38B O9 0.99 2.58 3.409(7) 141.6 2_645 C37 H37A O15 0.99 2.64 3.621(6) 171.0 2_655 C31 H31A O17 0.99 2.49 3.359(6) 146.4 2_645 C31 H31B O21 0.99 2.55 3.384(6) 142.1 4_565 C34 H34A O25 0.99 2.46 3.338(7) 147.2 . C18 H18 O19 0.95 2.40 3.300(5) 157.2 3_665 C25 H25 O18 0.95 2.43 3.241(6) 142.8 1_455 N1 H1NB O14 0.90(6) 2.03(6) 2.842(5) 150(5) . N1 H1NA O12 0.83(7) 2.25(7) 3.023(7) 157(6) 4_576 N1 H1NA O9 0.83(7) 2.52(7) 3.245(8) 147(5) 4_576 N2 H2NC O20 0.86(5) 2.22(6) 3.016(6) 155(4) 2_645 N2 H2NB O8 0.81(5) 2.04(6) 2.835(5) 165(5) 1_545 N2 H2NA O6 0.81(4) 2.15(5) 2.835(5) 142(4) 1_545 N4 H4NB O2 0.86(6) 1.99(6) 2.850(5) 175(5) . N4 H4NC O4 0.78(5) 2.13(5) 2.879(5) 160(5) . N4 H4NA O16 0.84(5) 2.14(5) 2.941(5) 160(4) . N3 H3NA O25 0.84(4) 1.86(4) 2.693(6) 168(3) 1_565 N3 H3NC O22 0.83(8) 2.25(9) 2.997(6) 150(7) 1_564 N3 H3NB O20 0.81(7) 2.25(7) 2.952(5) 145(6) 2_655 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.196 _refine_diff_density_min -0.412 _refine_diff_density_rms 0.091 #END*************************************************************** data_DADPM-15C5 _database_code_depnum_ccdc_archive 'CCDC 846232' #TrackingRef '- Structures(3).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C13 H16 N2),2(C10 H20 O5),2(Cl O4)' _chemical_formula_sum 'C33 H56 Cl2 N2 O18' _chemical_formula_weight 839.70 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8552(6) _cell_length_b 14.2350(9) _cell_length_c 16.8384(11) _cell_angle_alpha 110.236(1) _cell_angle_beta 95.478(1) _cell_angle_gamma 90.002(1) _cell_volume 1981.2(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5350 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 25.00 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.408 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 892 _exptl_absorpt_coefficient_mu 0.242 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9095 _exptl_absorpt_correction_T_max 0.9716 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD 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 17319 _diffrn_reflns_av_R_equivalents 0.0311 _diffrn_reflns_av_sigmaI/netI 0.0407 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.30 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6938 _reflns_number_gt 5881 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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. ; _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^)+(0.0636P)^2^+4.0643P] 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 6938 _refine_ls_number_parameters 530 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0743 _refine_ls_R_factor_gt 0.0638 _refine_ls_wR_factor_ref 0.1567 _refine_ls_wR_factor_gt 0.1490 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.5170(4) 0.3669(3) 0.3339(2) 0.0341(8) Uani 1 1 d . . . H1 H 0.5306 0.3946 0.2911 0.041 Uiso 1 1 calc R . . C2 C 0.5954(4) 0.2830(3) 0.3345(2) 0.0323(8) Uani 1 1 d . . . H2 H 0.6613 0.2527 0.2922 0.039 Uiso 1 1 calc R . . C3 C 0.5763(3) 0.2440(2) 0.39738(19) 0.0224(6) Uani 1 1 d . . . C4 C 0.4829(3) 0.2874(2) 0.45958(19) 0.0240(7) Uani 1 1 d . . . H4 H 0.4716 0.2604 0.5031 0.029 Uiso 1 1 calc R . . C5 C 0.4053(3) 0.3714(2) 0.4577(2) 0.0255(7) Uani 1 1 d . . . H5 H 0.3410 0.4022 0.5008 0.031 Uiso 1 1 calc R . . C6 C 0.4194(3) 0.4112(2) 0.39468(19) 0.0230(7) Uani 1 1 d . . . C7 C 0.3313(4) 0.5007(2) 0.3908(2) 0.0281(7) Uani 1 1 d . . . H7A H 0.4006 0.5487 0.3803 0.034 Uiso 1 1 calc R . . H7B H 0.2924 0.5346 0.4465 0.034 Uiso 1 1 calc R . . C8 C 0.1992(3) 0.4721(2) 0.32177(19) 0.0240(7) Uani 1 1 d . . . C9 C 0.0642(4) 0.4306(3) 0.3329(2) 0.0297(7) Uani 1 1 d . . . H9 H 0.0551 0.4190 0.3845 0.036 Uiso 1 1 calc R . . C10 C -0.0572(4) 0.4059(2) 0.2706(2) 0.0272(7) Uani 1 1 d . . . H10 H -0.1493 0.3787 0.2795 0.033 Uiso 1 1 calc R . . C11 C -0.0425(3) 0.4211(2) 0.19532(19) 0.0220(6) Uani 1 1 d . . . C12 C 0.0901(4) 0.4605(2) 0.1813(2) 0.0262(7) Uani 1 1 d . . . H12 H 0.0995 0.4699 0.1288 0.031 Uiso 1 1 calc R . . C13 C 0.2103(4) 0.4863(2) 0.2453(2) 0.0271(7) Uani 1 1 d . . . H13 H 0.3018 0.5142 0.2363 0.033 Uiso 1 1 calc R . . C14 C 0.6635(5) 0.4170(3) 0.9284(3) 0.0522(11) Uani 1 1 d . . . H14A H 0.6331 0.4833 0.9656 0.063 Uiso 1 1 calc R . . H14B H 0.6575 0.4180 0.8697 0.063 Uiso 1 1 calc R . . C15 C 0.5543(5) 0.3414(4) 0.9302(3) 0.0493(10) Uani 1 1 d . . . H15A H 0.4515 0.3542 0.9083 0.059 Uiso 1 1 calc R . . H15B H 0.5828 0.2738 0.8945 0.059 Uiso 1 1 calc R . . C16 C 0.4471(4) 0.2763(3) 1.0220(3) 0.0489(10) Uani 1 1 d . . . H16A H 0.4652 0.2086 0.9819 0.059 Uiso 1 1 calc R . . H16B H 0.3431 0.2946 1.0071 0.059 Uiso 1 1 calc R . . C17 C 0.4621(4) 0.2762(3) 1.1086(3) 0.0472(10) Uani 1 1 d . . . H17A H 0.4443 0.3442 1.1481 0.057 Uiso 1 1 calc R . . H17B H 0.3836 0.2299 1.1141 0.057 Uiso 1 1 calc R . . C18 C 0.6372(4) 0.1421(3) 1.1007(3) 0.0442(9) Uani 1 1 d . . . H18A H 0.5453 0.1039 1.0667 0.053 Uiso 1 1 calc R . . H18B H 0.6629 0.1185 1.1490 0.053 Uiso 1 1 calc R . . C19 C 0.7641(4) 0.1243(3) 1.0474(3) 0.0453(10) Uani 1 1 d . . . H19A H 0.7920 0.0532 1.0302 0.054 Uiso 1 1 calc R . . H19B H 0.7350 0.1403 0.9953 0.054 Uiso 1 1 calc R . . C20 C 1.0313(4) 0.1615(3) 1.0646(2) 0.0334(8) Uani 1 1 d . . . H20A H 1.0462 0.0895 1.0543 0.040 Uiso 1 1 calc R . . H20B H 1.1123 0.2000 1.1086 0.040 Uiso 1 1 calc R . . C21 C 1.0484(4) 0.1812(3) 0.9834(2) 0.0369(8) Uani 1 1 d . . . H21A H 1.1444 0.1538 0.9607 0.044 Uiso 1 1 calc R . . H21B H 0.9631 0.1483 0.9401 0.044 Uiso 1 1 calc R . . C22 C 1.0459(4) 0.3182(4) 0.9285(2) 0.0464(10) Uani 1 1 d . . . H22A H 1.1011 0.2702 0.8841 0.056 Uiso 1 1 calc R . . H22B H 1.0991 0.3845 0.9460 0.056 Uiso 1 1 calc R . . C23 C 0.8907(5) 0.3254(3) 0.8926(2) 0.0464(10) Uani 1 1 d . . . H23A H 0.8918 0.3413 0.8399 0.056 Uiso 1 1 calc R . . H23B H 0.8327 0.2613 0.8790 0.056 Uiso 1 1 calc R . . C24 C 0.9083(5) -0.0353(3) 0.2625(2) 0.0453(10) Uani 1 1 d . . . H24A H 1.0098 -0.0317 0.2939 0.054 Uiso 1 1 calc R . . H24B H 0.9151 -0.0756 0.2020 0.054 Uiso 1 1 calc R . . C25 C 0.7969(4) -0.0837(3) 0.2978(2) 0.0363(8) Uani 1 1 d . . . H25A H 0.6931 -0.0796 0.2719 0.044 Uiso 1 1 calc R . . H25B H 0.8196 -0.1552 0.2852 0.044 Uiso 1 1 calc R . . C26 C 0.7009(4) -0.0712(2) 0.4270(2) 0.0351(8) Uani 1 1 d . . . H26A H 0.7178 -0.1431 0.4165 0.042 Uiso 1 1 calc R . . H26B H 0.5963 -0.0645 0.4034 0.042 Uiso 1 1 calc R . . C27 C 0.7220(5) -0.0129(3) 0.5205(2) 0.0397(9) Uani 1 1 d . . . H27A H 0.6678 -0.0480 0.5515 0.048 Uiso 1 1 calc R . . H27B H 0.8312 -0.0073 0.5413 0.048 Uiso 1 1 calc R . . C28 C 0.7107(6) 0.1548(3) 0.6192(2) 0.0520(11) Uani 1 1 d . . . H28A H 0.7257 0.1187 0.6599 0.062 Uiso 1 1 calc R A 1 H28B H 0.6295 0.2031 0.6376 0.062 Uiso 1 1 calc R A 1 C30 C 0.9618(5) 0.3031(5) 0.5534(3) 0.0811(19) Uani 1 1 d . . . H30A H 1.0243 0.3192 0.6088 0.097 Uiso 1 1 calc R B 1 H30B H 0.9414 0.3675 0.5449 0.097 Uiso 1 1 calc R B 1 C32 C 1.0705(4) 0.1737(4) 0.3491(3) 0.0574(13) Uani 1 1 d . D . H32A H 1.1161 0.1214 0.3692 0.069 Uiso 1 1 calc R . . H32B H 1.1533 0.2179 0.3447 0.069 Uiso 1 1 calc R . . C33 C 0.9824(5) 0.1271(3) 0.2655(3) 0.0492(11) Uani 1 1 d . . . H33A H 0.9398 0.1802 0.2454 0.059 Uiso 1 1 calc R . . H33B H 1.0506 0.0877 0.2238 0.059 Uiso 1 1 calc R . . C29A C 0.8500(6) 0.2090(4) 0.6208(3) 0.0429(16) Uani 0.827(12) 1 d P C 1 H29A H 0.9328 0.1617 0.6035 0.051 Uiso 0.50 1 calc PR C 1 H29B H 0.8801 0.2566 0.6789 0.051 Uiso 0.50 1 calc PR C 1 C31A C 1.0531(6) 0.2480(5) 0.4894(3) 0.045(2) Uani 0.725(13) 1 d P D 1 H31A H 1.0783 0.1833 0.4963 0.053 Uiso 0.50 1 calc PR D 1 H31B H 1.1491 0.2862 0.4943 0.053 Uiso 0.50 1 calc PR D 1 C29B C 0.742(2) 0.2470(13) 0.6261(11) 0.026(6) Uiso 0.173(12) 1 d P C 2 H29C H 0.8029 0.2797 0.6815 0.031 Uiso 0.50 1 calc PR C 2 H29D H 0.6456 0.2822 0.6279 0.031 Uiso 0.50 1 calc PR C 2 C31B C 0.9953(15) 0.3170(10) 0.4973(8) 0.029(4) Uiso 0.275(13) 1 d P D 2 H31C H 1.1047 0.3366 0.5084 0.035 Uiso 0.50 1 calc PR D 2 H31D H 0.9400 0.3757 0.4929 0.035 Uiso 0.50 1 calc PR D 2 Cl1 Cl 0.65747(8) 0.62451(6) 0.26930(4) 0.02451(19) Uani 1 1 d . . . Cl2 Cl 0.37442(9) 0.99086(6) 0.19782(5) 0.0267(2) Uani 1 1 d . . . N1 N 0.6566(3) 0.1536(2) 0.39540(19) 0.0244(6) Uani 1 1 d . . . N2 N -0.1722(3) 0.3968(2) 0.13024(18) 0.0231(6) Uani 1 1 d . . . O1 O 0.8246(3) 0.40301(17) 0.95554(14) 0.0338(6) Uani 1 1 d . . . O2 O 0.5565(3) 0.3479(2) 1.01531(15) 0.0440(7) Uani 1 1 d . . . O3 O 0.6076(3) 0.24645(19) 1.13210(17) 0.0402(6) Uani 1 1 d . . . O4 O 0.8879(2) 0.18739(16) 1.09664(14) 0.0276(5) Uani 1 1 d . . . O5 O 1.0492(3) 0.28562(18) 1.00142(14) 0.0340(6) Uani 1 1 d . . . O6 O 0.8620(3) 0.06324(19) 0.26999(15) 0.0378(6) Uani 1 1 d . . . O7 O 0.8076(3) -0.03238(16) 0.38747(13) 0.0285(5) Uani 1 1 d . . . O8 O 0.6638(3) 0.08462(17) 0.53608(15) 0.0372(6) Uani 1 1 d . C . O9 O 0.8223(3) 0.26274(19) 0.56171(14) 0.0380(6) Uani 1 1 d . C . O10 O 0.9701(3) 0.2303(3) 0.40681(16) 0.0563(8) Uani 1 1 d . . . O11 O 0.5995(3) 0.52512(17) 0.21764(15) 0.0346(6) Uani 1 1 d . . . O12 O 0.5477(3) 0.69535(19) 0.26269(17) 0.0478(7) Uani 1 1 d . . . O13 O 0.7955(3) 0.64316(18) 0.23879(16) 0.0398(6) Uani 1 1 d . . . O14 O 0.6852(3) 0.6313(2) 0.35578(15) 0.0471(7) Uani 1 1 d . . . O15 O 0.4222(3) 1.0232(2) 0.28711(15) 0.0483(7) Uani 1 1 d . . . O16 O 0.2525(3) 0.9197(2) 0.18099(18) 0.0572(8) Uani 1 1 d . . . O17 O 0.4978(3) 0.9464(2) 0.15072(17) 0.0489(7) Uani 1 1 d . . . O18 O 0.3245(3) 1.0730(2) 0.1745(2) 0.0631(9) Uani 1 1 d . . . H2NB H -0.146(4) 0.396(2) 0.081(2) 0.025(9) Uiso 1 1 d . . . H1NC H 0.606(4) 0.103(3) 0.358(3) 0.035(10) Uiso 1 1 d . . . H1NB H 0.662(4) 0.143(3) 0.442(3) 0.038(11) Uiso 1 1 d . . . H2NA H -0.217(4) 0.340(3) 0.125(2) 0.038(11) Uiso 1 1 d . . . H2NC H -0.243(5) 0.438(3) 0.146(2) 0.038(11) Uiso 1 1 d . . . H1NA H 0.755(6) 0.154(3) 0.382(3) 0.064(14) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.037(2) 0.040(2) 0.0348(19) 0.0244(16) 0.0053(15) 0.0076(16) C2 0.0332(19) 0.0372(19) 0.0322(18) 0.0173(15) 0.0096(15) 0.0114(15) C3 0.0192(15) 0.0218(15) 0.0256(16) 0.0092(13) -0.0044(12) -0.0016(12) C4 0.0271(17) 0.0232(16) 0.0228(15) 0.0104(13) -0.0015(13) -0.0018(13) C5 0.0227(16) 0.0251(16) 0.0242(16) 0.0042(13) -0.0022(13) -0.0007(13) C6 0.0197(15) 0.0187(15) 0.0267(16) 0.0058(12) -0.0092(12) -0.0046(12) C7 0.0258(17) 0.0239(16) 0.0320(18) 0.0093(14) -0.0095(14) -0.0006(13) C8 0.0248(16) 0.0167(14) 0.0267(16) 0.0048(12) -0.0052(13) 0.0016(12) C9 0.0303(18) 0.0355(18) 0.0244(16) 0.0135(14) -0.0037(13) -0.0018(14) C10 0.0238(16) 0.0315(17) 0.0266(16) 0.0109(14) 0.0011(13) -0.0028(13) C11 0.0212(15) 0.0173(14) 0.0224(15) 0.0021(12) -0.0047(12) 0.0015(12) C12 0.0285(17) 0.0268(16) 0.0227(16) 0.0087(13) -0.0011(13) -0.0026(13) C13 0.0235(16) 0.0234(16) 0.0327(18) 0.0082(14) 0.0000(13) -0.0024(13) C14 0.056(3) 0.056(3) 0.049(2) 0.033(2) -0.028(2) -0.018(2) C15 0.039(2) 0.071(3) 0.040(2) 0.024(2) -0.0065(17) -0.002(2) C16 0.0209(18) 0.051(2) 0.066(3) 0.010(2) -0.0035(18) -0.0035(17) C17 0.030(2) 0.049(2) 0.065(3) 0.020(2) 0.0098(19) 0.0014(17) C18 0.037(2) 0.036(2) 0.057(2) 0.0131(18) 0.0079(18) -0.0074(17) C19 0.035(2) 0.035(2) 0.052(2) -0.0020(18) 0.0021(18) -0.0063(16) C20 0.0247(17) 0.0253(17) 0.045(2) 0.0072(15) -0.0012(15) 0.0053(14) C21 0.0238(17) 0.048(2) 0.0279(18) -0.0010(16) 0.0025(14) 0.0018(16) C22 0.037(2) 0.075(3) 0.0281(19) 0.0173(19) 0.0111(16) -0.004(2) C23 0.063(3) 0.043(2) 0.034(2) 0.0165(18) 0.0009(19) -0.001(2) C24 0.061(3) 0.042(2) 0.033(2) 0.0102(17) 0.0170(18) 0.022(2) C25 0.049(2) 0.0268(18) 0.0253(17) 0.0005(14) -0.0011(15) 0.0088(16) C26 0.043(2) 0.0223(17) 0.044(2) 0.0154(15) 0.0075(16) 0.0036(15) C27 0.054(2) 0.036(2) 0.038(2) 0.0224(17) 0.0118(17) 0.0077(17) C28 0.084(3) 0.046(2) 0.0251(19) 0.0088(17) 0.014(2) 0.000(2) C30 0.037(2) 0.124(5) 0.045(3) -0.019(3) 0.002(2) -0.022(3) C32 0.025(2) 0.094(4) 0.079(3) 0.065(3) 0.001(2) -0.001(2) C33 0.050(2) 0.063(3) 0.051(2) 0.037(2) 0.023(2) 0.024(2) C29A 0.044(3) 0.056(3) 0.024(2) 0.009(2) -0.0053(19) 0.012(2) C31A 0.032(3) 0.058(4) 0.039(3) 0.013(3) -0.004(2) -0.005(3) Cl1 0.0241(4) 0.0255(4) 0.0202(4) 0.0037(3) 0.0003(3) 0.0015(3) Cl2 0.0258(4) 0.0279(4) 0.0250(4) 0.0089(3) -0.0036(3) -0.0051(3) N1 0.0262(16) 0.0229(15) 0.0233(15) 0.0078(12) -0.0011(12) 0.0024(12) N2 0.0221(14) 0.0225(15) 0.0221(15) 0.0056(12) -0.0021(11) -0.0003(12) O1 0.0459(15) 0.0285(12) 0.0268(12) 0.0100(10) 0.0020(10) 0.0014(11) O2 0.0304(14) 0.0734(19) 0.0298(13) 0.0211(13) -0.0014(11) 0.0018(13) O3 0.0279(13) 0.0382(14) 0.0603(17) 0.0224(13) 0.0121(12) 0.0061(11) O4 0.0263(12) 0.0232(11) 0.0306(12) 0.0069(9) -0.0001(9) 0.0000(9) O5 0.0332(13) 0.0439(14) 0.0244(12) 0.0111(11) 0.0043(10) 0.0098(11) O6 0.0438(15) 0.0419(14) 0.0331(13) 0.0176(11) 0.0119(11) 0.0121(12) O7 0.0358(13) 0.0246(11) 0.0221(11) 0.0046(9) 0.0019(9) 0.0028(10) O8 0.0574(16) 0.0268(12) 0.0296(13) 0.0109(10) 0.0105(11) 0.0059(11) O9 0.0391(14) 0.0450(15) 0.0252(12) 0.0080(11) -0.0041(10) -0.0111(11) O10 0.0443(16) 0.091(2) 0.0303(14) 0.0190(15) -0.0052(12) -0.0331(16) O11 0.0288(13) 0.0302(13) 0.0379(14) 0.0041(11) 0.0000(10) -0.0008(10) O12 0.0473(16) 0.0389(15) 0.0473(16) 0.0045(12) -0.0023(13) 0.0194(12) O13 0.0401(15) 0.0359(14) 0.0464(15) 0.0154(12) 0.0147(12) -0.0004(11) O14 0.0470(16) 0.0697(19) 0.0220(12) 0.0144(12) -0.0034(11) -0.0049(14) O15 0.0579(18) 0.0503(16) 0.0253(13) 0.0014(12) -0.0056(12) -0.0174(14) O16 0.0593(19) 0.0602(19) 0.0442(16) 0.0118(14) -0.0088(14) -0.0369(15) O17 0.0493(17) 0.0538(17) 0.0439(16) 0.0155(13) 0.0117(13) 0.0084(14) O18 0.0531(18) 0.076(2) 0.091(2) 0.064(2) 0.0266(17) 0.0267(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.384(5) . ? C1 C2 1.384(5) . ? C1 H1 0.9500 . ? C2 C3 1.377(4) . ? C2 H2 0.9500 . ? C3 C4 1.371(4) . ? C3 N1 1.462(4) . ? C4 C5 1.388(4) . ? C4 H4 0.9500 . ? C5 C6 1.380(4) . ? C5 H5 0.9500 . ? C6 C7 1.511(4) . ? C7 C8 1.516(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C13 1.383(4) . ? C8 C9 1.391(5) . ? C9 C10 1.382(4) . ? C9 H9 0.9500 . ? C10 C11 1.375(4) . ? C10 H10 0.9500 . ? C11 C12 1.376(4) . ? C11 N2 1.462(4) . ? C12 C13 1.391(4) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C15 1.457(6) . ? C14 O1 1.491(5) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 O2 1.402(4) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 O2 1.445(5) . ? C16 C17 1.452(6) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 O3 1.419(4) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 O3 1.428(4) . ? C18 C19 1.472(5) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 O4 1.417(4) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 O4 1.425(4) . ? C20 C21 1.509(5) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 O5 1.410(4) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 O5 1.453(4) . ? C22 C23 1.466(6) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 O1 1.412(5) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 O6 1.428(4) . ? C24 C25 1.480(5) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 O7 1.426(4) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 O7 1.419(4) . ? C26 C27 1.498(5) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 O8 1.426(4) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 C29B 1.305(17) . ? C28 O8 1.432(4) . ? C28 C29A 1.448(7) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C30 C31B 1.098(12) . ? C30 O9 1.401(5) . ? C30 C31A 1.418(7) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C32 O10 1.417(6) . ? C32 C33 1.474(6) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 O6 1.426(5) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C29A O9 1.454(5) . ? C29A H29A 0.9900 . ? C29A H29B 0.9900 . ? C31A O10 1.449(6) . ? C31A H31A 0.9900 . ? C31A H31B 0.9900 . ? C29B O9 1.428(17) . ? C29B H29C 0.9900 . ? C29B H29D 0.9900 . ? C31B O10 1.590(12) . ? C31B H31C 0.9900 . ? C31B H31D 0.9900 . ? Cl1 O14 1.423(2) . ? Cl1 O12 1.425(3) . ? Cl1 O13 1.429(3) . ? Cl1 O11 1.444(2) . ? Cl2 O18 1.415(3) . ? Cl2 O16 1.420(3) . ? Cl2 O17 1.429(3) . ? Cl2 O15 1.432(2) . ? N1 H1NC 0.86(4) . ? N1 H1NB 0.85(4) . ? N1 H1NA 0.92(5) . ? N2 H2NB 0.88(4) . ? N2 H2NA 0.87(4) . ? N2 H2NC 0.85(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 C6 C1 C2 121.1(3) . . ? C6 C1 H1 119.5 . . ? C2 C1 H1 119.5 . . ? C3 C2 C1 119.0(3) . . ? C3 C2 H2 120.5 . . ? C1 C2 H2 120.5 . . ? C4 C3 C2 121.3(3) . . ? C4 C3 N1 120.5(3) . . ? C2 C3 N1 118.2(3) . . ? C3 C4 C5 118.7(3) . . ? C3 C4 H4 120.7 . . ? C5 C4 H4 120.7 . . ? C6 C5 C4 121.5(3) . . ? C6 C5 H5 119.2 . . ? C4 C5 H5 119.2 . . ? C5 C6 C1 118.3(3) . . ? C5 C6 C7 121.7(3) . . ? C1 C6 C7 120.0(3) . . ? C6 C7 C8 112.6(2) . . ? C6 C7 H7A 109.1 . . ? C8 C7 H7A 109.1 . . ? C6 C7 H7B 109.1 . . ? C8 C7 H7B 109.1 . . ? H7A C7 H7B 107.8 . . ? C13 C8 C9 118.0(3) . . ? C13 C8 C7 120.6(3) . . ? C9 C8 C7 121.4(3) . . ? C10 C9 C8 121.5(3) . . ? C10 C9 H9 119.3 . . ? C8 C9 H9 119.3 . . ? C11 C10 C9 119.0(3) . . ? C11 C10 H10 120.5 . . ? C9 C10 H10 120.5 . . ? C10 C11 C12 121.2(3) . . ? C10 C11 N2 118.8(3) . . ? C12 C11 N2 120.0(3) . . ? C11 C12 C13 118.9(3) . . ? C11 C12 H12 120.5 . . ? C13 C12 H12 120.5 . . ? C8 C13 C12 121.3(3) . . ? C8 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? C15 C14 O1 115.7(3) . . ? C15 C14 H14A 108.4 . . ? O1 C14 H14A 108.4 . . ? C15 C14 H14B 108.4 . . ? O1 C14 H14B 108.4 . . ? H14A C14 H14B 107.4 . . ? O2 C15 C14 106.8(3) . . ? O2 C15 H15A 110.4 . . ? C14 C15 H15A 110.4 . . ? O2 C15 H15B 110.4 . . ? C14 C15 H15B 110.4 . . ? H15A C15 H15B 108.6 . . ? O2 C16 C17 109.0(3) . . ? O2 C16 H16A 109.9 . . ? C17 C16 H16A 109.9 . . ? O2 C16 H16B 109.9 . . ? C17 C16 H16B 109.9 . . ? H16A C16 H16B 108.3 . . ? O3 C17 C16 112.2(3) . . ? O3 C17 H17A 109.2 . . ? C16 C17 H17A 109.2 . . ? O3 C17 H17B 109.2 . . ? C16 C17 H17B 109.2 . . ? H17A C17 H17B 107.9 . . ? O3 C18 C19 109.9(3) . . ? O3 C18 H18A 109.7 . . ? C19 C18 H18A 109.7 . . ? O3 C18 H18B 109.7 . . ? C19 C18 H18B 109.7 . . ? H18A C18 H18B 108.2 . . ? O4 C19 C18 107.2(3) . . ? O4 C19 H19A 110.3 . . ? C18 C19 H19A 110.3 . . ? O4 C19 H19B 110.3 . . ? C18 C19 H19B 110.3 . . ? H19A C19 H19B 108.5 . . ? O4 C20 C21 114.1(3) . . ? O4 C20 H20A 108.7 . . ? C21 C20 H20A 108.7 . . ? O4 C20 H20B 108.7 . . ? C21 C20 H20B 108.7 . . ? H20A C20 H20B 107.6 . . ? O5 C21 C20 108.5(3) . . ? O5 C21 H21A 110.0 . . ? C20 C21 H21A 110.0 . . ? O5 C21 H21B 110.0 . . ? C20 C21 H21B 110.0 . . ? H21A C21 H21B 108.4 . . ? O5 C22 C23 112.3(3) . . ? O5 C22 H22A 109.2 . . ? C23 C22 H22A 109.2 . . ? O5 C22 H22B 109.2 . . ? C23 C22 H22B 109.2 . . ? H22A C22 H22B 107.9 . . ? O1 C23 C22 106.1(3) . . ? O1 C23 H23A 110.5 . . ? C22 C23 H23A 110.5 . . ? O1 C23 H23B 110.5 . . ? C22 C23 H23B 110.5 . . ? H23A C23 H23B 108.7 . . ? O6 C24 C25 109.6(3) . . ? O6 C24 H24A 109.7 . . ? C25 C24 H24A 109.7 . . ? O6 C24 H24B 109.7 . . ? C25 C24 H24B 109.7 . . ? H24A C24 H24B 108.2 . . ? O7 C25 C24 107.9(3) . . ? O7 C25 H25A 110.1 . . ? C24 C25 H25A 110.1 . . ? O7 C25 H25B 110.1 . . ? C24 C25 H25B 110.1 . . ? H25A C25 H25B 108.4 . . ? O7 C26 C27 107.9(3) . . ? O7 C26 H26A 110.1 . . ? C27 C26 H26A 110.1 . . ? O7 C26 H26B 110.1 . . ? C27 C26 H26B 110.1 . . ? H26A C26 H26B 108.4 . . ? O8 C27 C26 109.4(3) . . ? O8 C27 H27A 109.8 . . ? C26 C27 H27A 109.8 . . ? O8 C27 H27B 109.8 . . ? C26 C27 H27B 109.8 . . ? H27A C27 H27B 108.2 . . ? C29B C28 O8 117.9(8) . . ? C29B C28 C29A 46.4(9) . . ? O8 C28 C29A 111.9(3) . . ? C29B C28 H28A 132.3 . . ? O8 C28 H28A 109.2 . . ? C29A C28 H28A 109.2 . . ? C29B C28 H28B 63.9 . . ? O8 C28 H28B 109.2 . . ? C29A C28 H28B 109.2 . . ? H28A C28 H28B 107.9 . . ? C31B C30 O9 127.0(8) . . ? C31B C30 C31A 48.8(7) . . ? O9 C30 C31A 120.6(5) . . ? C31B C30 H30A 125.9 . . ? O9 C30 H30A 107.2 . . ? C31A C30 H30A 107.2 . . ? C31B C30 H30B 58.9 . . ? O9 C30 H30B 107.2 . . ? C31A C30 H30B 107.2 . . ? H30A C30 H30B 106.8 . . ? O10 C32 C33 107.9(3) . . ? O10 C32 H32A 110.1 . . ? C33 C32 H32A 110.1 . . ? O10 C32 H32B 110.1 . . ? C33 C32 H32B 110.1 . . ? H32A C32 H32B 108.4 . . ? O6 C33 C32 111.4(3) . . ? O6 C33 H33A 109.4 . . ? C32 C33 H33A 109.4 . . ? O6 C33 H33B 109.4 . . ? C32 C33 H33B 109.4 . . ? H33A C33 H33B 108.0 . . ? C28 C29A O9 107.6(3) . . ? C28 C29A H29A 110.2 . . ? O9 C29A H29A 110.2 . . ? C28 C29A H29B 110.2 . . ? O9 C29A H29B 110.2 . . ? H29A C29A H29B 108.5 . . ? C30 C31A O10 108.9(4) . . ? C30 C31A H31A 109.9 . . ? O10 C31A H31A 109.9 . . ? C30 C31A H31B 109.9 . . ? O10 C31A H31B 109.9 . . ? H31A C31A H31B 108.3 . . ? C28 C29B O9 117.8(13) . . ? C28 C29B H29C 107.8 . . ? O9 C29B H29C 107.8 . . ? C28 C29B H29D 107.8 . . ? O9 C29B H29D 107.8 . . ? H29C C29B H29D 107.2 . . ? C30 C31B O10 119.3(10) . . ? C30 C31B H31C 107.5 . . ? O10 C31B H31C 107.5 . . ? C30 C31B H31D 107.5 . . ? O10 C31B H31D 107.5 . . ? H31C C31B H31D 107.0 . . ? O14 Cl1 O12 109.28(17) . . ? O14 Cl1 O13 110.03(16) . . ? O12 Cl1 O13 110.35(17) . . ? O14 Cl1 O11 109.81(16) . . ? O12 Cl1 O11 108.95(15) . . ? O13 Cl1 O11 108.41(14) . . ? O18 Cl2 O16 109.5(2) . . ? O18 Cl2 O17 109.36(17) . . ? O16 Cl2 O17 110.35(19) . . ? O18 Cl2 O15 110.4(2) . . ? O16 Cl2 O15 107.47(17) . . ? O17 Cl2 O15 109.73(17) . . ? C3 N1 H1NC 108(2) . . ? C3 N1 H1NB 114(3) . . ? H1NC N1 H1NB 106(3) . . ? C3 N1 H1NA 113(3) . . ? H1NC N1 H1NA 110(4) . . ? H1NB N1 H1NA 106(4) . . ? C11 N2 H2NB 112(2) . . ? C11 N2 H2NA 111(2) . . ? H2NB N2 H2NA 111(3) . . ? C11 N2 H2NC 111(3) . . ? H2NB N2 H2NC 111(3) . . ? H2NA N2 H2NC 101(4) . . ? C23 O1 C14 112.0(3) . . ? C15 O2 C16 109.6(3) . . ? C17 O3 C18 117.6(3) . . ? C19 O4 C20 114.7(3) . . ? C21 O5 C22 116.1(3) . . ? C33 O6 C24 113.5(3) . . ? C26 O7 C25 112.2(3) . . ? C27 O8 C28 114.2(3) . . ? C30 O9 C29B 139.3(8) . . ? C30 O9 C29A 107.8(4) . . ? C29B O9 C29A 44.5(8) . . ? C32 O10 C31A 103.5(3) . . ? C32 O10 C31B 133.3(5) . . ? C31A O10 C31B 41.3(5) . . ? 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 C16 H16A O17 0.99 2.59 3.555(5) 165.6 2_666 C16 H16B O5 0.99 2.60 3.514(4) 154.2 1_455 C21 H21B O16 0.99 2.58 3.559(4) 172.5 2_666 C33 H33B O18 0.99 2.62 3.491(5) 146.4 1_645 N1 H1NC O15 0.86(4) 2.02(4) 2.831(4) 157(3) 1_545 N1 H1NB O8 0.85(4) 2.02(4) 2.857(4) 167(4) . N1 H1NA O10 0.92(5) 2.12(5) 2.948(4) 148(4) . N2 H2NC O11 0.85(4) 2.06(4) 2.881(4) 162(4) 1_455 N2 H2NA O3 0.87(4) 2.08(4) 2.905(4) 157(3) 1_454 N2 H2NB O1 0.88(4) 2.14(4) 2.971(4) 158(3) 1_454 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.978 _refine_diff_density_min -0.568 _refine_diff_density_rms 0.075 #END********************************************************** data_DADPM-18C6 _database_code_depnum_ccdc_archive 'CCDC 846233' #TrackingRef '- Structures(3).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C76 H143 Cl4 N5 O46' _chemical_formula_weight 2004.75 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 16.1814(9) _cell_length_b 21.7220(12) _cell_length_c 29.3019(17) _cell_angle_alpha 90.00 _cell_angle_beta 103.233(1) _cell_angle_gamma 90.00 _cell_volume 10025.9(10) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7067 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 24.36 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.326 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4268 _exptl_absorpt_coefficient_mu 0.210 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.9022 _exptl_absorpt_correction_T_max 0.9632 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD 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 83366 _diffrn_reflns_av_R_equivalents 0.0517 _diffrn_reflns_av_sigmaI/netI 0.0445 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 1.33 _diffrn_reflns_theta_max 25.00 _reflns_number_total 17646 _reflns_number_gt 14233 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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. ; _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^)+(0.0760P)^2^+23.1367P] 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 17646 _refine_ls_number_parameters 1228 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0919 _refine_ls_R_factor_gt 0.0759 _refine_ls_wR_factor_ref 0.1931 _refine_ls_wR_factor_gt 0.1842 _refine_ls_goodness_of_fit_ref 1.115 _refine_ls_restrained_S_all 1.115 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7700(2) 0.24361(16) 0.97225(12) 0.0147(7) Uani 1 1 d . . . C2 C 0.8166(2) 0.19006(16) 0.97345(13) 0.0195(8) Uani 1 1 d . . . H2 H 0.7971 0.1524 0.9838 0.023 Uiso 1 1 calc R . . C3 C 0.8929(2) 0.19271(17) 0.95914(13) 0.0219(8) Uani 1 1 d . . . H3 H 0.9262 0.1565 0.9604 0.026 Uiso 1 1 calc R . . C4 C 0.9214(2) 0.24700(17) 0.94307(12) 0.0179(8) Uani 1 1 d . . . C5 C 0.8742(2) 0.30002(17) 0.94386(12) 0.0186(8) Uani 1 1 d . . . H5 H 0.8941 0.3379 0.9342 0.022 Uiso 1 1 calc R . . C6 C 0.7984(2) 0.29893(16) 0.95847(12) 0.0174(7) Uani 1 1 d . . . H6 H 0.7666 0.3356 0.9590 0.021 Uiso 1 1 calc R . . C7 C 1.0028(2) 0.24893(19) 0.92529(13) 0.0223(8) Uani 1 1 d . . . H7A H 1.0055 0.2119 0.9059 0.027 Uiso 1 1 calc R . . H7B H 1.0016 0.2855 0.9050 0.027 Uiso 1 1 calc R . . C8 C 1.0814(2) 0.25140(17) 0.96467(12) 0.0178(8) Uani 1 1 d . . . C9 C 1.1233(2) 0.19721(17) 0.98277(12) 0.0183(8) Uani 1 1 d . . . H9 H 1.1023 0.1585 0.9702 0.022 Uiso 1 1 calc R . . C10 C 1.1956(2) 0.19992(16) 1.01904(12) 0.0179(7) Uani 1 1 d . . . H10 H 1.2241 0.1632 1.0313 0.021 Uiso 1 1 calc R . . C11 C 1.2255(2) 0.25636(15) 1.03715(11) 0.0126(7) Uani 1 1 d . . . C12 C 1.1842(2) 0.31045(15) 1.02040(12) 0.0157(7) Uani 1 1 d . . . H12 H 1.2046 0.3491 1.0336 0.019 Uiso 1 1 calc R . . C13 C 1.1126(2) 0.30709(17) 0.98404(13) 0.0192(8) Uani 1 1 d . . . H13 H 1.0842 0.3440 0.9721 0.023 Uiso 1 1 calc R . . C14 C 0.4872(2) 0.27155(16) 0.29010(12) 0.0148(7) Uani 1 1 d . . . C15 C 0.4469(2) 0.32774(16) 0.29038(13) 0.0206(8) Uani 1 1 d . . . H15 H 0.4705 0.3640 0.2804 0.025 Uiso 1 1 calc R . . C16 C 0.3719(2) 0.33043(17) 0.30534(13) 0.0223(8) Uani 1 1 d . . . H16 H 0.3441 0.3689 0.3055 0.027 Uiso 1 1 calc R . . C17 C 0.3365(2) 0.27795(17) 0.32008(12) 0.0174(7) Uani 1 1 d . . . C18 C 0.3768(2) 0.22197(16) 0.31789(12) 0.0163(7) Uani 1 1 d . . . H18 H 0.3525 0.1855 0.3270 0.020 Uiso 1 1 calc R . . C19 C 0.4515(2) 0.21827(16) 0.30277(12) 0.0155(7) Uani 1 1 d . . . H19 H 0.4781 0.1796 0.3011 0.019 Uiso 1 1 calc R . . C20 C 0.2557(2) 0.28147(18) 0.33787(12) 0.0196(8) Uani 1 1 d . . . H20A H 0.2561 0.2483 0.3611 0.024 Uiso 1 1 calc R . . H20B H 0.2538 0.3214 0.3539 0.024 Uiso 1 1 calc R . . C21 C 0.1778(2) 0.27517(17) 0.29880(12) 0.0169(7) Uani 1 1 d . . . C22 C 0.1365(2) 0.32626(17) 0.27607(12) 0.0182(8) Uani 1 1 d . . . H22 H 0.1573 0.3662 0.2857 0.022 Uiso 1 1 calc R . . C23 C 0.0651(2) 0.32033(16) 0.23948(12) 0.0168(7) Uani 1 1 d . . . H23 H 0.0374 0.3558 0.2243 0.020 Uiso 1 1 calc R . . C24 C 0.0351(2) 0.26237(16) 0.22556(12) 0.0136(7) Uani 1 1 d . . . C25 C 0.0756(2) 0.21025(17) 0.24668(13) 0.0189(8) Uani 1 1 d . . . H25 H 0.0552 0.1705 0.2362 0.023 Uiso 1 1 calc R . . C26 C 0.1466(2) 0.21662(16) 0.28331(13) 0.0191(8) Uani 1 1 d . . . H26 H 0.1745 0.1809 0.2981 0.023 Uiso 1 1 calc R . . C27 C 0.6280(2) 0.39734(16) 1.03165(14) 0.0238(8) Uani 1 1 d . . . H27A H 0.6509 0.4336 1.0509 0.029 Uiso 1 1 calc R . . H27B H 0.5700 0.3893 1.0359 0.029 Uiso 1 1 calc R . . C28 C 0.6247(3) 0.41028(16) 0.98139(14) 0.0259(9) Uani 1 1 d . . . H28A H 0.5886 0.4467 0.9709 0.031 Uiso 1 1 calc R . . H28B H 0.6825 0.4191 0.9771 0.031 Uiso 1 1 calc R . . C29 C 0.5843(3) 0.36636(18) 0.90581(13) 0.0252(9) Uani 1 1 d . . . H29A H 0.6415 0.3660 0.8991 0.030 Uiso 1 1 calc R . . H29B H 0.5574 0.4065 0.8957 0.030 Uiso 1 1 calc R . . C30 C 0.5322(3) 0.31571(19) 0.88017(14) 0.0288(9) Uani 1 1 d . . . H30A H 0.4749 0.3164 0.8869 0.035 Uiso 1 1 calc R . . H30B H 0.5257 0.3213 0.8460 0.035 Uiso 1 1 calc R . . C31 C 0.5225(3) 0.2070(2) 0.87258(14) 0.0292(9) Uani 1 1 d . . . H31A H 0.5100 0.2119 0.8381 0.035 Uiso 1 1 calc R . . H31B H 0.4679 0.2061 0.8824 0.035 Uiso 1 1 calc R . . C32 C 0.5695(3) 0.14836(19) 0.88628(14) 0.0279(9) Uani 1 1 d . . . H32A H 0.5375 0.1136 0.8687 0.033 Uiso 1 1 calc R . . H32B H 0.6258 0.1504 0.8785 0.033 Uiso 1 1 calc R . . C33 C 0.6204(3) 0.08130(17) 0.94922(15) 0.0293(9) Uani 1 1 d . . . H33A H 0.6769 0.0806 0.9416 0.035 Uiso 1 1 calc R . . H33B H 0.5860 0.0473 0.9321 0.035 Uiso 1 1 calc R . . C34 C 0.6299(3) 0.07317(17) 1.00109(15) 0.0297(9) Uani 1 1 d . . . H34A H 0.5732 0.0710 1.0084 0.036 Uiso 1 1 calc R . . H34B H 0.6603 0.0343 1.0115 0.036 Uiso 1 1 calc R . . C35 C 0.6955(3) 0.11632(19) 1.07433(14) 0.0300(9) Uani 1 1 d . . . H35A H 0.7287 0.0781 1.0830 0.036 Uiso 1 1 calc R . . H35B H 0.6424 0.1130 1.0855 0.036 Uiso 1 1 calc R . . C36 C 0.7459(3) 0.17073(18) 1.09661(14) 0.0287(9) Uani 1 1 d . . . H36A H 0.7636 0.1646 1.1309 0.034 Uiso 1 1 calc R . . H36B H 0.7977 0.1752 1.0843 0.034 Uiso 1 1 calc R . . C37 C 0.7390(3) 0.27714(19) 1.10960(14) 0.0276(9) Uani 1 1 d . . . H37A H 0.7944 0.2818 1.1010 0.033 Uiso 1 1 calc R . . H37B H 0.7497 0.2718 1.1440 0.033 Uiso 1 1 calc R . . C38 C 0.6861(3) 0.33300(18) 1.09519(13) 0.0262(9) Uani 1 1 d . . . H38A H 0.6285 0.3265 1.1005 0.031 Uiso 1 1 calc R . . H38B H 0.7118 0.3687 1.1142 0.031 Uiso 1 1 calc R . . C39 C 0.7378(3) 0.2992(2) 0.38861(15) 0.0406(12) Uani 1 1 d . . . H39A H 0.7914 0.3000 0.3778 0.049 Uiso 1 1 calc R . . H39B H 0.7519 0.2929 0.4230 0.049 Uiso 1 1 calc R . . C40 C 0.6920(3) 0.3587(2) 0.37705(15) 0.0400(12) Uani 1 1 d . . . H40A H 0.6369 0.3572 0.3863 0.048 Uiso 1 1 calc R . . H40B H 0.7261 0.3927 0.3944 0.048 Uiso 1 1 calc R . . C41 C 0.6369(3) 0.42617(18) 0.31472(15) 0.0314(10) Uani 1 1 d . . . H41A H 0.6705 0.4600 0.3326 0.038 Uiso 1 1 calc R . . H41B H 0.5803 0.4259 0.3222 0.038 Uiso 1 1 calc R . . C42 C 0.6275(3) 0.43644(17) 0.26336(16) 0.0299(10) Uani 1 1 d . . . H42A H 0.5956 0.4750 0.2538 0.036 Uiso 1 1 calc R . . H42B H 0.6842 0.4404 0.2563 0.036 Uiso 1 1 calc R . . C43 C 0.5643(3) 0.39480(17) 0.18864(14) 0.0260(9) Uani 1 1 d . . . H43A H 0.6176 0.3988 0.1778 0.031 Uiso 1 1 calc R . . H43B H 0.5310 0.4331 0.1805 0.031 Uiso 1 1 calc R . . C44 C 0.5147(3) 0.34102(18) 0.16549(14) 0.0268(9) Uani 1 1 d . . . H44A H 0.4622 0.3364 0.1772 0.032 Uiso 1 1 calc R . . H44B H 0.4982 0.3478 0.1312 0.032 Uiso 1 1 calc R . . C45 C 0.5219(3) 0.23508(19) 0.15032(14) 0.0285(9) Uani 1 1 d . . . H45A H 0.5149 0.2415 0.1162 0.034 Uiso 1 1 calc R . . H45B H 0.4648 0.2308 0.1569 0.034 Uiso 1 1 calc R . . C46 C 0.5722(3) 0.17850(19) 0.16508(14) 0.0282(9) Uani 1 1 d . . . H46A H 0.5474 0.1435 0.1449 0.034 Uiso 1 1 calc R . . H46B H 0.6313 0.1845 0.1620 0.034 Uiso 1 1 calc R . . C47 C 0.6180(3) 0.11083(18) 0.22791(17) 0.0366(11) Uani 1 1 d . . . H47A H 0.6768 0.1152 0.2239 0.044 Uiso 1 1 calc R . . H47B H 0.5913 0.0755 0.2087 0.044 Uiso 1 1 calc R . . C48 C 0.6189(3) 0.09960(18) 0.27829(18) 0.0389(11) Uani 1 1 d . . . H48A H 0.5602 0.0950 0.2823 0.047 Uiso 1 1 calc R . . H48B H 0.6505 0.0613 0.2891 0.047 Uiso 1 1 calc R . . C49 C 0.6661(3) 0.1425(2) 0.35351(16) 0.0383(11) Uani 1 1 d . . . H49A H 0.6900 0.1013 0.3634 0.046 Uiso 1 1 calc R . . H49B H 0.6095 0.1454 0.3608 0.046 Uiso 1 1 calc R . . C50 C 0.7226(3) 0.1909(2) 0.37899(15) 0.0393(12) Uani 1 1 d . . . H50A H 0.7309 0.1845 0.4132 0.047 Uiso 1 1 calc R . . H50B H 0.7787 0.1885 0.3710 0.047 Uiso 1 1 calc R . . C51 C 0.8384(3) 0.1882(2) 0.26784(15) 0.0352(10) Uani 1 1 d . . . H51A H 0.8952 0.1936 0.2888 0.042 Uiso 1 1 calc R . . H51B H 0.8061 0.1586 0.2826 0.042 Uiso 1 1 calc R . . C52 C 0.7925(3) 0.24950(18) 0.26108(14) 0.0272(9) Uani 1 1 d . . . H52A H 0.7367 0.2446 0.2389 0.033 Uiso 1 1 calc R . . H52B H 0.7824 0.2639 0.2914 0.033 Uiso 1 1 calc R . . C53 C 0.8008(3) 0.3513(2) 0.23826(15) 0.0331(10) Uani 1 1 d . . . H53A H 0.7936 0.3658 0.2691 0.040 Uiso 1 1 calc R . . H53B H 0.7437 0.3473 0.2172 0.040 Uiso 1 1 calc R . . C54 C 0.8521(3) 0.39744(18) 0.21833(15) 0.0290(9) Uani 1 1 d . . . H54A H 0.8220 0.4374 0.2138 0.035 Uiso 1 1 calc R . . H54B H 0.9077 0.4037 0.2404 0.035 Uiso 1 1 calc R . . C55 C 0.9068(3) 0.4192(2) 0.15247(14) 0.0316(10) Uani 1 1 d . . . H55A H 0.9641 0.4274 0.1722 0.038 Uiso 1 1 calc R . . H55B H 0.8747 0.4584 0.1482 0.038 Uiso 1 1 calc R . . C56 C 0.9143(3) 0.39508(18) 0.10591(15) 0.0306(9) Uani 1 1 d . . . H56A H 0.8571 0.3872 0.0859 0.037 Uiso 1 1 calc R . . H56B H 0.9430 0.4258 0.0900 0.037 Uiso 1 1 calc R . . C57 C 0.9711(3) 0.3142(2) 0.06969(15) 0.0342(10) Uani 1 1 d . . . H57A H 1.0009 0.3441 0.0536 0.041 Uiso 1 1 calc R . . H57B H 0.9143 0.3064 0.0494 0.041 Uiso 1 1 calc R . . C58 C 1.0197(3) 0.25607(19) 0.07756(15) 0.0338(10) Uani 1 1 d . . . H58A H 1.0290 0.2408 0.0473 0.041 Uiso 1 1 calc R . . H58B H 1.0760 0.2639 0.0986 0.041 Uiso 1 1 calc R . . C59 C 1.0207(3) 0.1542(2) 0.10502(18) 0.0442(12) Uani 1 1 d . . . H59A H 1.0751 0.1598 0.1282 0.053 Uiso 1 1 calc R . . H59B H 1.0334 0.1399 0.0753 0.053 Uiso 1 1 calc R . . C60 C 0.9683(3) 0.10766(19) 0.12234(16) 0.0355(10) Uani 1 1 d . . . H60A H 0.9152 0.1005 0.0984 0.043 Uiso 1 1 calc R . . H60B H 0.9997 0.0682 0.1281 0.043 Uiso 1 1 calc R . . C61 C 0.8994(3) 0.08504(19) 0.18246(17) 0.0355(10) Uani 1 1 d . . . H61A H 0.9290 0.0448 0.1866 0.043 Uiso 1 1 calc R . . H61B H 0.8440 0.0795 0.1600 0.043 Uiso 1 1 calc R . . C62 C 0.8854(3) 0.10709(18) 0.22877(15) 0.0327(10) Uani 1 1 d . . . H62A H 0.8489 0.0773 0.2406 0.039 Uiso 1 1 calc R . . H62B H 0.9406 0.1094 0.2518 0.039 Uiso 1 1 calc R . . C63 C 0.2920(3) 0.19821(18) 0.19131(13) 0.0244(8) Uani 1 1 d . . . H63A H 0.3502 0.2053 0.2103 0.029 Uiso 1 1 calc R . . H63B H 0.2636 0.1682 0.2081 0.029 Uiso 1 1 calc R . . C64 C 0.2440(3) 0.25707(17) 0.18520(14) 0.0240(8) Uani 1 1 d . . . H64A H 0.1875 0.2506 0.1640 0.029 Uiso 1 1 calc R . . H64B H 0.2354 0.2712 0.2159 0.029 Uiso 1 1 calc R . . C65 C 0.2464(2) 0.36029(17) 0.16064(14) 0.0237(8) Uani 1 1 d . . . H65A H 0.2342 0.3730 0.1908 0.028 Uiso 1 1 calc R . . H65B H 0.1919 0.3566 0.1372 0.028 Uiso 1 1 calc R . . C66 C 0.3017(2) 0.40749(16) 0.14485(13) 0.0198(8) Uani 1 1 d . . . H66A H 0.2733 0.4481 0.1417 0.024 Uiso 1 1 calc R . . H66B H 0.3563 0.4112 0.1683 0.024 Uiso 1 1 calc R . . C67 C 0.3680(2) 0.43121(16) 0.08241(13) 0.0202(8) Uani 1 1 d . . . H67A H 0.4253 0.4334 0.1034 0.024 Uiso 1 1 calc R . . H67B H 0.3423 0.4727 0.0805 0.024 Uiso 1 1 calc R . . C68 C 0.3745(2) 0.41041(16) 0.03467(13) 0.0200(8) Uani 1 1 d . . . H68A H 0.3172 0.4087 0.0136 0.024 Uiso 1 1 calc R . . H68B H 0.4092 0.4400 0.0214 0.024 Uiso 1 1 calc R . . C69 C 0.4141(2) 0.32762(17) -0.00715(13) 0.0220(8) Uani 1 1 d . . . H69A H 0.4418 0.3577 -0.0242 0.026 Uiso 1 1 calc R . . H69B H 0.3553 0.3210 -0.0254 0.026 Uiso 1 1 calc R . . C70 C 0.4618(2) 0.26797(17) -0.00203(13) 0.0205(8) Uani 1 1 d . . . H70A H 0.4710 0.2548 -0.0328 0.025 Uiso 1 1 calc R . . H70B H 0.5180 0.2733 0.0197 0.025 Uiso 1 1 calc R . . C71 C 0.4567(2) 0.16422(17) 0.02090(14) 0.0234(8) Uani 1 1 d . . . H71A H 0.5126 0.1682 0.0431 0.028 Uiso 1 1 calc R . . H71B H 0.4664 0.1507 -0.0097 0.028 Uiso 1 1 calc R . . C72 C 0.4043(2) 0.11760(16) 0.03868(13) 0.0209(8) Uani 1 1 d . . . H72A H 0.3489 0.1126 0.0161 0.025 Uiso 1 1 calc R . . H72B H 0.4337 0.0773 0.0424 0.025 Uiso 1 1 calc R . . C73 C 0.3476(2) 0.09382(16) 0.10391(13) 0.0209(8) Uani 1 1 d . . . H73A H 0.3785 0.0541 0.1073 0.025 Uiso 1 1 calc R . . H73B H 0.2900 0.0871 0.0841 0.025 Uiso 1 1 calc R . . C74 C 0.3417(2) 0.11738(16) 0.15133(13) 0.0216(8) Uani 1 1 d . . . H74A H 0.3125 0.0866 0.1670 0.026 Uiso 1 1 calc R . . H74B H 0.3995 0.1238 0.1711 0.026 Uiso 1 1 calc R . . C75 C 0.1129(3) 0.9713(3) 0.1004(2) 0.0648(17) Uani 1 1 d . . . H75A H 0.0777 0.9504 0.1188 0.097 Uiso 1 1 calc R . . H75B H 0.1009 0.9541 0.0686 0.097 Uiso 1 1 calc R . . H75C H 0.0998 1.0154 0.0987 0.097 Uiso 1 1 calc R . . C76 C 0.2013(3) 0.9624(2) 0.12237(16) 0.0341(10) Uani 1 1 d . . . Cl1 Cl 0.62942(6) 0.53409(4) 0.12286(3) 0.0196(2) Uani 1 1 d . . . Cl2 Cl 0.61150(6) 0.97899(4) 0.13853(4) 0.0269(2) Uani 1 1 d . . . Cl3 Cl 0.14539(6) 0.01719(4) 0.23951(4) 0.0284(2) Uani 1 1 d . . . Cl4 Cl 0.13577(6) 0.50522(4) 0.04921(3) 0.0266(2) Uani 1 1 d . . . H1NA H 0.688(3) 0.272(2) 1.0055(17) 0.039(13) Uiso 1 1 d . . . H2NA H 1.313(3) 0.299(2) 1.0823(16) 0.040(13) Uiso 1 1 d . . . H3NA H 0.574(3) 0.295(2) 0.2665(18) 0.034(16) Uiso 1 1 d . . . H4NA H -0.051(2) 0.221(2) 0.1815(13) 0.015(11) Uiso 1 1 d . . . H1NB H 0.653(3) 0.245(2) 0.9621(17) 0.027(13) Uiso 1 1 d . . . H2NB H 1.306(3) 0.237(2) 1.0928(17) 0.027(13) Uiso 1 1 d . . . H3NB H 0.600(3) 0.266(2) 0.2992(19) 0.031(16) Uiso 1 1 d . . . H4NB H -0.081(3) 0.264(2) 0.1972(16) 0.028(14) Uiso 1 1 d . . . H1NC H 0.681(3) 0.208(2) 0.9982(16) 0.033(13) Uiso 1 1 d . . . H2NC H 1.347(3) 0.245(2) 1.0640(16) 0.036(13) Uiso 1 1 d . . . H3NC H 0.568(4) 0.234(3) 0.256(2) 0.064(17) Uiso 1 1 d . . . H4NC H -0.048(3) 0.277(2) 0.165(2) 0.050(16) Uiso 1 1 d . . . N1 N 0.6873(2) 0.24147(16) 0.98461(13) 0.0158(6) Uani 1 1 d . . . N2 N 1.3048(2) 0.25919(15) 1.07330(11) 0.0134(6) Uani 1 1 d . . . N3 N 0.5696(2) 0.26832(17) 0.27749(14) 0.0165(7) Uani 1 1 d . . . N4 N -0.0428(2) 0.25656(16) 0.18886(12) 0.0144(6) Uani 1 1 d . . . N5 N 0.2709(3) 0.95544(17) 0.14032(14) 0.0375(9) Uani 1 1 d . . . O1 O 0.68081(16) 0.34500(11) 1.04683(9) 0.0210(6) Uani 1 1 d . . . O2 O 0.59059(16) 0.35773(11) 0.95438(9) 0.0225(6) Uani 1 1 d . . . O3 O 0.57226(16) 0.25771(12) 0.89434(9) 0.0239(6) Uani 1 1 d . . . O4 O 0.57971(17) 0.13880(12) 0.93542(9) 0.0252(6) Uani 1 1 d . . . O5 O 0.67623(17) 0.12390(11) 1.02500(9) 0.0234(6) Uani 1 1 d . . . O6 O 0.69541(16) 0.22472(12) 1.08660(9) 0.0238(6) Uani 1 1 d . . . O7 O 0.68571(17) 0.25019(15) 0.36644(10) 0.0326(7) Uani 1 1 d . . . O8 O 0.67834(17) 0.36901(13) 0.32782(10) 0.0294(6) Uani 1 1 d . . . O9 O 0.58308(16) 0.38564(11) 0.23810(9) 0.0216(6) Uani 1 1 d . . . O10 O 0.56478(16) 0.28670(12) 0.17541(9) 0.0220(6) Uani 1 1 d . . . O11 O 0.57117(17) 0.16569(12) 0.21282(10) 0.0257(6) Uani 1 1 d . . . O12 O 0.65884(18) 0.15040(13) 0.30490(10) 0.0302(7) Uani 1 1 d . . . O13 O 0.84670(18) 0.16527(12) 0.22426(10) 0.0303(7) Uani 1 1 d . . . O14 O 0.84159(18) 0.29351(13) 0.24340(10) 0.0293(6) Uani 1 1 d . . . O15 O 0.86472(18) 0.37607(12) 0.17495(10) 0.0292(6) Uani 1 1 d . . . O16 O 0.96246(18) 0.33914(13) 0.11289(10) 0.0304(6) Uani 1 1 d . . . O17 O 0.97699(19) 0.21083(14) 0.09759(11) 0.0357(7) Uani 1 1 d . . . O18 O 0.94881(19) 0.12865(13) 0.16465(10) 0.0332(7) Uani 1 1 d . . . O19 O 0.29594(16) 0.17413(11) 0.14650(8) 0.0190(5) Uani 1 1 d . . . O20 O 0.28914(16) 0.30273(11) 0.16599(9) 0.0203(6) Uani 1 1 d . . . O21 O 0.31678(16) 0.38857(11) 0.10056(9) 0.0196(5) Uani 1 1 d . . . O22 O 0.41278(15) 0.35097(11) 0.03787(8) 0.0186(5) Uani 1 1 d . . . O23 O 0.41447(16) 0.22233(11) 0.01576(9) 0.0192(5) Uani 1 1 d . . . O24 O 0.39155(16) 0.13818(11) 0.08273(9) 0.0199(6) Uani 1 1 d . . . O25 O 0.69732(18) 0.49503(13) 0.14622(11) 0.0351(7) Uani 1 1 d . . . O26 O 0.6557(2) 0.56258(15) 0.08414(12) 0.0451(8) Uani 1 1 d . . . O27 O 0.6131(2) 0.57970(19) 0.15379(14) 0.0658(12) Uani 1 1 d . . . O28 O 0.55513(18) 0.49868(14) 0.10475(12) 0.0379(7) Uani 1 1 d . . . O29 O 0.6194(2) 0.93058(18) 0.10736(14) 0.0611(11) Uani 1 1 d . . . O30 O 0.68942(19) 1.01192(15) 0.15365(12) 0.0436(8) Uani 1 1 d . . . O31 O 0.54558(19) 1.02047(14) 0.11656(11) 0.0368(7) Uani 1 1 d . . . O32 O 0.5890(2) 0.95320(15) 0.17938(11) 0.0411(8) Uani 1 1 d . . . O33 O 0.21035(18) -0.02829(14) 0.25596(11) 0.0367(7) Uani 1 1 d . . . O34 O 0.1736(3) 0.05924(16) 0.20912(15) 0.0667(12) Uani 1 1 d . . . O35 O 0.1282(2) 0.04963(17) 0.27900(12) 0.0503(9) Uani 1 1 d . . . O36 O 0.0711(2) -0.01273(16) 0.21509(15) 0.0575(10) Uani 1 1 d . . . O37 O 0.1520(2) 0.46048(14) 0.01669(12) 0.0463(9) Uani 1 1 d . . . O38 O 0.21212(18) 0.54136(14) 0.06567(11) 0.0355(7) Uani 1 1 d . . . O39 O 0.06823(19) 0.54533(13) 0.02713(11) 0.0377(7) Uani 1 1 d . . . O40 O 0.11433(19) 0.47503(14) 0.08843(11) 0.0378(7) Uani 1 1 d . . . O41 O 0.27193(18) 0.08905(12) 0.34560(10) 0.0321(7) Uani 1 1 d . . . O42 O 0.41900(19) 0.06561(12) 0.32850(10) 0.0313(7) Uani 1 1 d . . . O43 O 0.53117(18) 0.06484(13) 0.40527(10) 0.0332(7) Uani 1 1 d . . . O44 O 0.6893(2) 0.01589(15) 0.43098(11) 0.0410(8) Uani 1 1 d . . . O45 O 0.4331(2) 0.98606(14) 0.19776(11) 0.0373(7) Uani 1 1 d . . . O46 O 0.38569(18) 0.97730(12) 0.27598(10) 0.0294(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 C1 0.0094(17) 0.0211(18) 0.0127(17) -0.0035(14) 0.0006(14) 0.0027(14) C2 0.0180(19) 0.0170(18) 0.023(2) 0.0006(15) 0.0035(15) -0.0003(15) C3 0.0165(19) 0.024(2) 0.024(2) -0.0052(16) 0.0026(16) 0.0044(15) C4 0.0122(18) 0.0266(19) 0.0138(18) -0.0023(15) 0.0006(14) -0.0004(15) C5 0.0166(19) 0.0210(18) 0.0162(18) 0.0027(14) -0.0002(15) -0.0019(15) C6 0.0148(18) 0.0179(18) 0.0172(18) -0.0031(14) -0.0008(14) 0.0016(14) C7 0.0126(19) 0.039(2) 0.0145(18) -0.0011(16) 0.0017(15) 0.0001(16) C8 0.0127(18) 0.031(2) 0.0115(17) -0.0017(15) 0.0068(14) -0.0020(15) C9 0.0140(18) 0.0216(18) 0.0205(19) -0.0074(15) 0.0061(15) -0.0002(15) C10 0.0158(19) 0.0179(18) 0.0201(19) -0.0004(14) 0.0043(15) 0.0039(14) C11 0.0093(17) 0.0201(17) 0.0088(16) -0.0003(13) 0.0032(13) -0.0023(13) C12 0.0156(18) 0.0130(17) 0.0185(18) -0.0006(14) 0.0041(15) -0.0046(14) C13 0.0155(19) 0.0208(19) 0.0216(19) 0.0070(15) 0.0047(15) 0.0041(15) C14 0.0118(17) 0.0207(18) 0.0110(17) 0.0016(13) 0.0007(14) 0.0006(14) C15 0.0177(19) 0.0168(18) 0.028(2) 0.0035(15) 0.0061(16) -0.0020(15) C16 0.018(2) 0.0197(19) 0.028(2) 0.0032(15) 0.0040(16) 0.0057(15) C17 0.0133(18) 0.0261(19) 0.0119(17) -0.0013(14) 0.0013(14) -0.0010(15) C18 0.0138(18) 0.0202(18) 0.0129(17) 0.0019(14) -0.0010(14) -0.0049(14) C19 0.0162(18) 0.0148(17) 0.0138(17) -0.0006(13) 0.0000(14) 0.0001(14) C20 0.0119(18) 0.029(2) 0.0181(19) 0.0005(15) 0.0041(15) 0.0000(15) C21 0.0081(17) 0.029(2) 0.0148(18) 0.0007(15) 0.0057(14) 0.0014(15) C22 0.0157(19) 0.0195(18) 0.0197(19) -0.0061(14) 0.0046(15) 0.0000(14) C23 0.0155(18) 0.0162(17) 0.0188(18) 0.0032(14) 0.0041(15) 0.0049(14) C24 0.0086(17) 0.0200(18) 0.0123(17) 0.0032(13) 0.0024(13) 0.0020(14) C25 0.0134(18) 0.0185(18) 0.025(2) 0.0012(15) 0.0042(15) -0.0021(14) C26 0.0142(19) 0.0180(18) 0.025(2) 0.0095(15) 0.0040(15) 0.0039(14) C27 0.020(2) 0.0148(18) 0.038(2) -0.0061(16) 0.0091(17) 0.0013(15) C28 0.031(2) 0.0124(18) 0.036(2) -0.0003(16) 0.0132(19) 0.0014(16) C29 0.023(2) 0.028(2) 0.026(2) 0.0111(16) 0.0070(17) 0.0040(17) C30 0.022(2) 0.040(2) 0.023(2) 0.0092(18) 0.0032(17) 0.0078(18) C31 0.023(2) 0.047(3) 0.018(2) -0.0097(18) 0.0048(17) -0.0084(19) C32 0.026(2) 0.036(2) 0.024(2) -0.0150(17) 0.0112(17) -0.0095(18) C33 0.026(2) 0.0175(19) 0.046(3) -0.0120(18) 0.0133(19) -0.0022(16) C34 0.028(2) 0.0152(19) 0.050(3) 0.0004(17) 0.016(2) 0.0006(16) C35 0.031(2) 0.029(2) 0.031(2) 0.0135(18) 0.0092(19) 0.0057(18) C36 0.025(2) 0.033(2) 0.027(2) 0.0074(17) 0.0021(17) 0.0060(18) C37 0.026(2) 0.036(2) 0.020(2) -0.0053(17) 0.0015(17) -0.0067(18) C38 0.029(2) 0.029(2) 0.020(2) -0.0076(16) 0.0051(17) -0.0037(17) C39 0.024(2) 0.079(4) 0.018(2) -0.006(2) 0.0022(18) 0.005(2) C40 0.029(2) 0.068(3) 0.024(2) -0.020(2) 0.0090(19) -0.006(2) C41 0.021(2) 0.028(2) 0.047(3) -0.0218(19) 0.0115(19) -0.0047(17) C42 0.028(2) 0.0140(18) 0.052(3) -0.0056(18) 0.018(2) -0.0040(16) C43 0.024(2) 0.022(2) 0.035(2) 0.0136(17) 0.0116(18) 0.0066(16) C44 0.025(2) 0.032(2) 0.024(2) 0.0064(17) 0.0052(17) 0.0090(17) C45 0.023(2) 0.039(2) 0.022(2) -0.0092(17) 0.0019(17) -0.0062(18) C46 0.026(2) 0.030(2) 0.032(2) -0.0118(18) 0.0129(18) -0.0062(17) C47 0.039(3) 0.0140(19) 0.061(3) -0.0025(19) 0.019(2) 0.0017(18) C48 0.040(3) 0.0128(19) 0.071(3) 0.009(2) 0.025(2) 0.0043(18) C49 0.026(2) 0.049(3) 0.043(3) 0.030(2) 0.014(2) 0.013(2) C50 0.029(2) 0.065(3) 0.024(2) 0.025(2) 0.0075(19) 0.019(2) C51 0.031(2) 0.051(3) 0.025(2) 0.013(2) 0.0105(19) -0.005(2) C52 0.029(2) 0.031(2) 0.025(2) 0.0043(17) 0.0135(18) 0.0028(17) C53 0.029(2) 0.038(2) 0.030(2) -0.0104(19) 0.0043(19) 0.0086(19) C54 0.032(2) 0.022(2) 0.035(2) -0.0090(17) 0.0137(19) -0.0010(17) C55 0.028(2) 0.037(2) 0.027(2) 0.0069(18) 0.0022(18) -0.0045(19) C56 0.041(3) 0.022(2) 0.030(2) 0.0029(17) 0.0099(19) -0.0030(18) C57 0.036(3) 0.044(3) 0.025(2) 0.0037(19) 0.0129(19) -0.003(2) C58 0.046(3) 0.034(2) 0.029(2) 0.0032(18) 0.025(2) 0.003(2) C59 0.048(3) 0.043(3) 0.046(3) -0.004(2) 0.019(2) 0.012(2) C60 0.042(3) 0.024(2) 0.044(3) -0.0040(19) 0.018(2) 0.0065(19) C61 0.029(2) 0.024(2) 0.051(3) 0.0052(19) 0.003(2) 0.0004(18) C62 0.041(3) 0.021(2) 0.039(3) 0.0110(18) 0.016(2) -0.0010(18) C63 0.029(2) 0.027(2) 0.0177(19) -0.0008(15) 0.0071(17) -0.0054(17) C64 0.029(2) 0.024(2) 0.023(2) -0.0024(16) 0.0147(17) -0.0061(17) C65 0.026(2) 0.0212(19) 0.026(2) -0.0042(16) 0.0104(17) 0.0002(16) C66 0.023(2) 0.0165(18) 0.0200(19) -0.0041(14) 0.0052(16) 0.0016(15) C67 0.0164(19) 0.0164(18) 0.028(2) 0.0040(15) 0.0051(16) -0.0021(14) C68 0.0184(19) 0.0161(18) 0.026(2) 0.0066(15) 0.0061(16) 0.0009(15) C69 0.020(2) 0.026(2) 0.0195(19) 0.0042(15) 0.0039(16) -0.0014(16) C70 0.022(2) 0.027(2) 0.0151(18) -0.0010(15) 0.0085(15) -0.0019(16) C71 0.022(2) 0.024(2) 0.027(2) 0.0008(16) 0.0098(17) 0.0069(16) C72 0.021(2) 0.0187(18) 0.024(2) -0.0057(15) 0.0080(16) -0.0011(15) C73 0.021(2) 0.0150(18) 0.025(2) 0.0037(15) 0.0027(16) -0.0008(15) C74 0.025(2) 0.0148(18) 0.025(2) 0.0060(15) 0.0061(16) -0.0008(15) C75 0.041(3) 0.087(4) 0.062(4) -0.023(3) 0.003(3) 0.024(3) C76 0.039(3) 0.030(2) 0.037(3) -0.0032(19) 0.017(2) 0.006(2) Cl1 0.0206(5) 0.0166(4) 0.0213(5) -0.0013(3) 0.0043(4) -0.0016(3) Cl2 0.0212(5) 0.0239(5) 0.0368(6) 0.0020(4) 0.0089(4) 0.0012(4) Cl3 0.0283(5) 0.0223(5) 0.0343(6) 0.0005(4) 0.0064(4) 0.0000(4) Cl4 0.0239(5) 0.0254(5) 0.0312(5) -0.0024(4) 0.0078(4) 0.0054(4) N1 0.0126(17) 0.0169(17) 0.0175(18) -0.0017(14) 0.0028(14) -0.0011(13) N2 0.0123(16) 0.0143(16) 0.0140(16) 0.0027(13) 0.0040(13) 0.0011(12) N3 0.0155(18) 0.0146(18) 0.0184(19) 0.0055(15) 0.0022(16) 0.0017(13) N4 0.0136(18) 0.0143(17) 0.0152(17) 0.0028(13) 0.0034(13) 0.0009(13) N5 0.033(2) 0.036(2) 0.045(2) 0.0017(17) 0.0132(19) 0.0036(17) O1 0.0208(14) 0.0197(13) 0.0227(14) -0.0042(10) 0.0055(11) 0.0001(11) O2 0.0234(14) 0.0205(13) 0.0253(14) 0.0015(11) 0.0088(11) 0.0018(11) O3 0.0182(14) 0.0299(15) 0.0211(14) -0.0033(11) -0.0008(11) 0.0010(11) O4 0.0268(15) 0.0227(14) 0.0281(15) -0.0092(11) 0.0104(12) -0.0041(11) O5 0.0255(15) 0.0165(13) 0.0290(15) 0.0015(11) 0.0081(12) -0.0008(11) O6 0.0213(14) 0.0246(14) 0.0237(14) 0.0003(11) 0.0017(11) 0.0017(11) O7 0.0185(15) 0.0563(19) 0.0212(15) 0.0068(13) 0.0012(12) 0.0065(13) O8 0.0245(15) 0.0344(16) 0.0302(16) -0.0135(12) 0.0084(12) -0.0011(12) O9 0.0273(15) 0.0137(12) 0.0264(14) 0.0002(10) 0.0119(12) -0.0031(11) O10 0.0184(14) 0.0243(14) 0.0206(14) -0.0018(11) -0.0015(11) 0.0004(11) O11 0.0245(15) 0.0193(13) 0.0350(16) -0.0050(11) 0.0103(12) 0.0004(11) O12 0.0293(16) 0.0299(15) 0.0344(16) 0.0165(13) 0.0132(13) 0.0097(12) O13 0.0307(16) 0.0266(15) 0.0330(16) 0.0049(12) 0.0061(13) 0.0023(12) O14 0.0282(16) 0.0302(15) 0.0306(16) 0.0006(12) 0.0092(13) 0.0008(12) O15 0.0369(17) 0.0236(14) 0.0267(15) -0.0006(11) 0.0063(13) -0.0005(12) O16 0.0340(17) 0.0291(15) 0.0273(15) -0.0005(12) 0.0055(13) 0.0002(13) O17 0.0360(18) 0.0371(17) 0.0373(17) -0.0010(14) 0.0153(14) 0.0041(14) O18 0.0352(17) 0.0235(15) 0.0403(18) -0.0009(13) 0.0075(14) -0.0027(13) O19 0.0239(14) 0.0180(12) 0.0153(13) 0.0003(10) 0.0049(11) -0.0001(10) O20 0.0237(14) 0.0165(12) 0.0235(14) 0.0008(10) 0.0110(11) -0.0015(11) O21 0.0199(14) 0.0167(12) 0.0230(14) -0.0017(10) 0.0068(11) -0.0037(10) O22 0.0188(13) 0.0184(13) 0.0187(13) 0.0022(10) 0.0044(11) 0.0018(10) O23 0.0178(13) 0.0198(13) 0.0223(13) 0.0013(10) 0.0094(11) 0.0014(10) O24 0.0233(14) 0.0172(13) 0.0204(13) -0.0005(10) 0.0073(11) -0.0038(10) O25 0.0258(16) 0.0302(16) 0.0484(19) 0.0135(14) 0.0068(14) 0.0064(13) O26 0.0347(18) 0.052(2) 0.046(2) 0.0277(16) 0.0040(15) -0.0039(15) O27 0.052(2) 0.075(3) 0.061(2) -0.042(2) -0.0073(19) 0.023(2) O28 0.0242(16) 0.0345(17) 0.053(2) -0.0046(15) 0.0057(14) -0.0094(13) O29 0.061(3) 0.055(2) 0.073(3) -0.025(2) 0.029(2) 0.0062(19) O30 0.0230(16) 0.0415(18) 0.064(2) 0.0129(16) 0.0044(15) -0.0048(14) O31 0.0277(17) 0.0383(17) 0.0411(18) 0.0070(14) 0.0010(14) 0.0014(13) O32 0.0368(18) 0.0425(19) 0.0426(19) 0.0133(15) 0.0064(15) 0.0007(15) O33 0.0238(16) 0.0407(18) 0.0454(19) 0.0034(14) 0.0073(14) 0.0031(13) O34 0.096(3) 0.036(2) 0.081(3) 0.0178(19) 0.048(3) 0.007(2) O35 0.041(2) 0.060(2) 0.053(2) -0.0158(18) 0.0160(17) 0.0057(17) O36 0.035(2) 0.042(2) 0.084(3) -0.0106(19) -0.0112(19) 0.0054(16) O37 0.068(2) 0.0327(17) 0.0434(19) -0.0035(14) 0.0234(18) 0.0119(16) O38 0.0226(15) 0.0443(18) 0.0420(18) 0.0000(14) 0.0123(14) -0.0037(13) O39 0.0309(17) 0.0322(16) 0.0477(19) 0.0009(14) 0.0044(14) 0.0056(13) O40 0.0340(18) 0.0419(18) 0.0412(18) 0.0063(14) 0.0165(15) -0.0006(14) O41 0.0317(16) 0.0229(14) 0.0421(18) 0.0004(13) 0.0092(14) 0.0007(12) O42 0.0365(17) 0.0248(15) 0.0352(17) -0.0004(12) 0.0133(14) -0.0034(13) O43 0.0294(16) 0.0355(16) 0.0362(17) -0.0065(13) 0.0105(13) -0.0104(13) O44 0.0387(19) 0.0468(19) 0.0411(19) 0.0013(15) 0.0162(15) 0.0004(15) O45 0.0371(18) 0.0415(18) 0.0370(17) -0.0029(14) 0.0164(14) 0.0013(14) O46 0.0298(16) 0.0273(15) 0.0313(16) -0.0028(12) 0.0078(13) 0.0027(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.379(5) . ? C1 C2 1.382(5) . ? C1 N1 1.465(5) . ? C2 C3 1.393(5) . ? C2 H2 0.9500 . ? C3 C4 1.387(5) . ? C3 H3 0.9500 . ? C4 C5 1.385(5) . ? C4 C7 1.524(5) . ? C5 C6 1.389(5) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.510(5) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C13 1.382(5) . ? C8 C9 1.401(5) . ? C9 C10 1.390(5) . ? C9 H9 0.9500 . ? C10 C11 1.379(5) . ? C10 H10 0.9500 . ? C11 C12 1.385(5) . ? C11 N2 1.466(4) . ? C12 C13 1.385(5) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C19 1.381(5) . ? C14 C15 1.385(5) . ? C14 N3 1.466(5) . ? C15 C16 1.382(5) . ? C15 H15 0.9500 . ? C16 C17 1.388(5) . ? C16 H16 0.9500 . ? C17 C18 1.388(5) . ? C17 C20 1.517(5) . ? C18 C19 1.382(5) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 C21 1.503(5) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.385(5) . ? C21 C26 1.405(5) . ? C22 C23 1.390(5) . ? C22 H22 0.9500 . ? C23 C24 1.377(5) . ? C23 H23 0.9500 . ? C24 C25 1.382(5) . ? C24 N4 1.463(5) . ? C25 C26 1.388(5) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 O1 1.431(4) . ? C27 C28 1.488(6) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 O2 1.426(5) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 O2 1.416(4) . ? C29 C30 1.482(6) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 O3 1.434(5) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 O3 1.425(5) . ? C31 C32 1.491(6) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 O4 1.426(5) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 O4 1.427(5) . ? C33 C34 1.503(6) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 O5 1.424(5) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 O5 1.417(5) . ? C35 C36 1.498(6) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 O6 1.421(5) . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? C37 O6 1.425(5) . ? C37 C38 1.489(6) . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? C38 O1 1.424(5) . ? C38 H38A 0.9900 . ? C38 H38B 0.9900 . ? C39 O7 1.419(6) . ? C39 C40 1.491(7) . ? C39 H39A 0.9900 . ? C39 H39B 0.9900 . ? C40 O8 1.426(5) . ? C40 H40A 0.9900 . ? C40 H40B 0.9900 . ? C41 O8 1.422(5) . ? C41 C42 1.494(6) . ? C41 H41A 0.9900 . ? C41 H41B 0.9900 . ? C42 O9 1.428(5) . ? C42 H42A 0.9900 . ? C42 H42B 0.9900 . ? C43 O9 1.425(5) . ? C43 C44 1.490(6) . ? C43 H43A 0.9900 . ? C43 H43B 0.9900 . ? C44 O10 1.424(5) . ? C44 H44A 0.9900 . ? C44 H44B 0.9900 . ? C45 O10 1.430(5) . ? C45 C46 1.482(6) . ? C45 H45A 0.9900 . ? C45 H45B 0.9900 . ? C46 O11 1.430(5) . ? C46 H46A 0.9900 . ? C46 H46B 0.9900 . ? C47 O11 1.427(5) . ? C47 C48 1.493(7) . ? C47 H47A 0.9900 . ? C47 H47B 0.9900 . ? C48 O12 1.418(5) . ? C48 H48A 0.9900 . ? C48 H48B 0.9900 . ? C49 O12 1.413(5) . ? C49 C50 1.478(7) . ? C49 H49A 0.9900 . ? C49 H49B 0.9900 . ? C50 O7 1.432(5) . ? C50 H50A 0.9900 . ? C50 H50B 0.9900 . ? C51 O13 1.406(5) . ? C51 C52 1.515(6) . ? C51 H51A 0.9900 . ? C51 H51B 0.9900 . ? C52 O14 1.415(5) . ? C52 H52A 0.9900 . ? C52 H52B 0.9900 . ? C53 O14 1.411(5) . ? C53 C54 1.502(6) . ? C53 H53A 0.9900 . ? C53 H53B 0.9900 . ? C54 O15 1.411(5) . ? C54 H54A 0.9900 . ? C54 H54B 0.9900 . ? C55 O15 1.407(5) . ? C55 C56 1.492(6) . ? C55 H55A 0.9900 . ? C55 H55B 0.9900 . ? C56 O16 1.433(5) . ? C56 H56A 0.9900 . ? C56 H56B 0.9900 . ? C57 O16 1.413(5) . ? C57 C58 1.478(6) . ? C57 H57A 0.9900 . ? C57 H57B 0.9900 . ? C58 O17 1.405(5) . ? C58 H58A 0.9900 . ? C58 H58B 0.9900 . ? C59 O17 1.410(5) . ? C59 C60 1.482(6) . ? C59 H59A 0.9900 . ? C59 H59B 0.9900 . ? C60 O18 1.423(5) . ? C60 H60A 0.9900 . ? C60 H60B 0.9900 . ? C61 O18 1.414(5) . ? C61 C62 1.504(6) . ? C61 H61A 0.9900 . ? C61 H61B 0.9900 . ? C62 O13 1.403(5) . ? C62 H62A 0.9900 . ? C62 H62B 0.9900 . ? C63 O19 1.428(4) . ? C63 C64 1.485(5) . ? C63 H63A 0.9900 . ? C63 H63B 0.9900 . ? C64 O20 1.422(4) . ? C64 H64A 0.9900 . ? C64 H64B 0.9900 . ? C65 O20 1.420(4) . ? C65 C66 1.502(5) . ? C65 H65A 0.9900 . ? C65 H65B 0.9900 . ? C66 O21 1.434(4) . ? C66 H66A 0.9900 . ? C66 H66B 0.9900 . ? C67 O21 1.425(4) . ? C67 C68 1.496(5) . ? C67 H67A 0.9900 . ? C67 H67B 0.9900 . ? C68 O22 1.426(4) . ? C68 H68A 0.9900 . ? C68 H68B 0.9900 . ? C69 O22 1.418(4) . ? C69 C70 1.498(5) . ? C69 H69A 0.9900 . ? C69 H69B 0.9900 . ? C70 O23 1.423(4) . ? C70 H70A 0.9900 . ? C70 H70B 0.9900 . ? C71 O23 1.427(4) . ? C71 C72 1.490(5) . ? C71 H71A 0.9900 . ? C71 H71B 0.9900 . ? C72 O24 1.425(4) . ? C72 H72A 0.9900 . ? C72 H72B 0.9900 . ? C73 O24 1.421(4) . ? C73 C74 1.504(5) . ? C73 H73A 0.9900 . ? C73 H73B 0.9900 . ? C74 O19 1.428(4) . ? C74 H74A 0.9900 . ? C74 H74B 0.9900 . ? C75 C76 1.442(7) . ? C75 H75A 0.9800 . ? C75 H75B 0.9800 . ? C75 H75C 0.9800 . ? C76 N5 1.139(6) . ? Cl1 O27 1.408(3) . ? Cl1 O28 1.423(3) . ? Cl1 O25 1.432(3) . ? Cl1 O26 1.439(3) . ? Cl2 O29 1.418(4) . ? Cl2 O30 1.429(3) . ? Cl2 O31 1.432(3) . ? Cl2 O32 1.441(3) . ? Cl3 O36 1.409(4) . ? Cl3 O34 1.422(4) . ? Cl3 O35 1.435(3) . ? Cl3 O33 1.443(3) . ? Cl4 O37 1.427(3) . ? Cl4 O39 1.431(3) . ? Cl4 O40 1.433(3) . ? Cl4 O38 1.450(3) . ? N1 H1NA 0.89(5) . ? N1 H1NB 0.76(5) . ? N1 H1NC 0.85(5) . ? N2 H2NA 0.90(5) . ? N2 H2NB 0.75(5) . ? N2 H2NC 0.85(5) . ? N3 H3NA 0.68(5) . ? N3 H3NB 0.71(5) . ? N3 H3NC 0.98(6) . ? N4 H4NA 0.81(4) . ? N4 H4NB 0.74(5) . ? N4 H4NC 0.82(6) . ? 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 C1 C2 121.6(3) . . ? C6 C1 N1 118.9(3) . . ? C2 C1 N1 119.4(3) . . ? C1 C2 C3 118.3(3) . . ? C1 C2 H2 120.9 . . ? C3 C2 H2 120.9 . . ? C4 C3 C2 121.6(3) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C5 C4 C3 118.3(3) . . ? C5 C4 C7 120.4(3) . . ? C3 C4 C7 121.3(3) . . ? C4 C5 C6 121.4(3) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C1 C6 C5 118.8(3) . . ? C1 C6 H6 120.6 . . ? C5 C6 H6 120.6 . . ? C8 C7 C4 112.5(3) . . ? C8 C7 H7A 109.1 . . ? C4 C7 H7A 109.1 . . ? C8 C7 H7B 109.1 . . ? C4 C7 H7B 109.1 . . ? H7A C7 H7B 107.8 . . ? C13 C8 C9 118.7(3) . . ? C13 C8 C7 120.6(3) . . ? C9 C8 C7 120.6(3) . . ? C10 C9 C8 120.2(3) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C11 C10 C9 119.5(3) . . ? C11 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? C10 C11 C12 121.3(3) . . ? C10 C11 N2 119.2(3) . . ? C12 C11 N2 119.5(3) . . ? C13 C12 C11 118.6(3) . . ? C13 C12 H12 120.7 . . ? C11 C12 H12 120.7 . . ? C8 C13 C12 121.7(3) . . ? C8 C13 H13 119.2 . . ? C12 C13 H13 119.2 . . ? C19 C14 C15 120.7(3) . . ? C19 C14 N3 119.2(3) . . ? C15 C14 N3 120.0(3) . . ? C16 C15 C14 119.2(3) . . ? C16 C15 H15 120.4 . . ? C14 C15 H15 120.4 . . ? C15 C16 C17 121.2(3) . . ? C15 C16 H16 119.4 . . ? C17 C16 H16 119.4 . . ? C18 C17 C16 118.3(3) . . ? C18 C17 C20 120.7(3) . . ? C16 C17 C20 121.0(3) . . ? C19 C18 C17 121.3(3) . . ? C19 C18 H18 119.3 . . ? C17 C18 H18 119.3 . . ? C14 C19 C18 119.1(3) . . ? C14 C19 H19 120.4 . . ? C18 C19 H19 120.4 . . ? C21 C20 C17 111.9(3) . . ? C21 C20 H20A 109.2 . . ? C17 C20 H20A 109.2 . . ? C21 C20 H20B 109.2 . . ? C17 C20 H20B 109.2 . . ? H20A C20 H20B 107.9 . . ? C22 C21 C26 118.2(3) . . ? C22 C21 C20 121.5(3) . . ? C26 C21 C20 120.3(3) . . ? C21 C22 C23 121.4(3) . . ? C21 C22 H22 119.3 . . ? C23 C22 H22 119.3 . . ? C24 C23 C22 119.2(3) . . ? C24 C23 H23 120.4 . . ? C22 C23 H23 120.4 . . ? C23 C24 C25 121.1(3) . . ? C23 C24 N4 118.9(3) . . ? C25 C24 N4 120.0(3) . . ? C24 C25 C26 119.3(3) . . ? C24 C25 H25 120.4 . . ? C26 C25 H25 120.4 . . ? C25 C26 C21 120.8(3) . . ? C25 C26 H26 119.6 . . ? C21 C26 H26 119.6 . . ? O1 C27 C28 110.0(3) . . ? O1 C27 H27A 109.7 . . ? C28 C27 H27A 109.7 . . ? O1 C27 H27B 109.7 . . ? C28 C27 H27B 109.7 . . ? H27A C27 H27B 108.2 . . ? O2 C28 C27 108.6(3) . . ? O2 C28 H28A 110.0 . . ? C27 C28 H28A 110.0 . . ? O2 C28 H28B 110.0 . . ? C27 C28 H28B 110.0 . . ? H28A C28 H28B 108.3 . . ? O2 C29 C30 108.3(3) . . ? O2 C29 H29A 110.0 . . ? C30 C29 H29A 110.0 . . ? O2 C29 H29B 110.0 . . ? C30 C29 H29B 110.0 . . ? H29A C29 H29B 108.4 . . ? O3 C30 C29 109.8(3) . . ? O3 C30 H30A 109.7 . . ? C29 C30 H30A 109.7 . . ? O3 C30 H30B 109.7 . . ? C29 C30 H30B 109.7 . . ? H30A C30 H30B 108.2 . . ? O3 C31 C32 109.8(3) . . ? O3 C31 H31A 109.7 . . ? C32 C31 H31A 109.7 . . ? O3 C31 H31B 109.7 . . ? C32 C31 H31B 109.7 . . ? H31A C31 H31B 108.2 . . ? O4 C32 C31 109.3(3) . . ? O4 C32 H32A 109.8 . . ? C31 C32 H32A 109.8 . . ? O4 C32 H32B 109.8 . . ? C31 C32 H32B 109.8 . . ? H32A C32 H32B 108.3 . . ? O4 C33 C34 108.8(3) . . ? O4 C33 H33A 109.9 . . ? C34 C33 H33A 109.9 . . ? O4 C33 H33B 109.9 . . ? C34 C33 H33B 109.9 . . ? H33A C33 H33B 108.3 . . ? O5 C34 C33 109.1(3) . . ? O5 C34 H34A 109.9 . . ? C33 C34 H34A 109.9 . . ? O5 C34 H34B 109.9 . . ? C33 C34 H34B 109.9 . . ? H34A C34 H34B 108.3 . . ? O5 C35 C36 108.9(3) . . ? O5 C35 H35A 109.9 . . ? C36 C35 H35A 109.9 . . ? O5 C35 H35B 109.9 . . ? C36 C35 H35B 109.9 . . ? H35A C35 H35B 108.3 . . ? O6 C36 C35 109.3(3) . . ? O6 C36 H36A 109.8 . . ? C35 C36 H36A 109.8 . . ? O6 C36 H36B 109.8 . . ? C35 C36 H36B 109.8 . . ? H36A C36 H36B 108.3 . . ? O6 C37 C38 109.1(3) . . ? O6 C37 H37A 109.9 . . ? C38 C37 H37A 109.9 . . ? O6 C37 H37B 109.9 . . ? C38 C37 H37B 109.9 . . ? H37A C37 H37B 108.3 . . ? O1 C38 C37 109.3(3) . . ? O1 C38 H38A 109.8 . . ? C37 C38 H38A 109.8 . . ? O1 C38 H38B 109.8 . . ? C37 C38 H38B 109.8 . . ? H38A C38 H38B 108.3 . . ? O7 C39 C40 109.6(4) . . ? O7 C39 H39A 109.8 . . ? C40 C39 H39A 109.8 . . ? O7 C39 H39B 109.8 . . ? C40 C39 H39B 109.8 . . ? H39A C39 H39B 108.2 . . ? O8 C40 C39 108.6(3) . . ? O8 C40 H40A 110.0 . . ? C39 C40 H40A 110.0 . . ? O8 C40 H40B 110.0 . . ? C39 C40 H40B 110.0 . . ? H40A C40 H40B 108.3 . . ? O8 C41 C42 109.6(3) . . ? O8 C41 H41A 109.7 . . ? C42 C41 H41A 109.7 . . ? O8 C41 H41B 109.7 . . ? C42 C41 H41B 109.7 . . ? H41A C41 H41B 108.2 . . ? O9 C42 C41 109.3(3) . . ? O9 C42 H42A 109.8 . . ? C41 C42 H42A 109.8 . . ? O9 C42 H42B 109.8 . . ? C41 C42 H42B 109.8 . . ? H42A C42 H42B 108.3 . . ? O9 C43 C44 108.7(3) . . ? O9 C43 H43A 109.9 . . ? C44 C43 H43A 109.9 . . ? O9 C43 H43B 109.9 . . ? C44 C43 H43B 109.9 . . ? H43A C43 H43B 108.3 . . ? O10 C44 C43 109.5(3) . . ? O10 C44 H44A 109.8 . . ? C43 C44 H44A 109.8 . . ? O10 C44 H44B 109.8 . . ? C43 C44 H44B 109.8 . . ? H44A C44 H44B 108.2 . . ? O10 C45 C46 109.3(3) . . ? O10 C45 H45A 109.8 . . ? C46 C45 H45A 109.8 . . ? O10 C45 H45B 109.8 . . ? C46 C45 H45B 109.8 . . ? H45A C45 H45B 108.3 . . ? O11 C46 C45 108.6(3) . . ? O11 C46 H46A 110.0 . . ? C45 C46 H46A 110.0 . . ? O11 C46 H46B 110.0 . . ? C45 C46 H46B 110.0 . . ? H46A C46 H46B 108.4 . . ? O11 C47 C48 109.1(3) . . ? O11 C47 H47A 109.9 . . ? C48 C47 H47A 109.9 . . ? O11 C47 H47B 109.9 . . ? C48 C47 H47B 109.9 . . ? H47A C47 H47B 108.3 . . ? O12 C48 C47 108.5(3) . . ? O12 C48 H48A 110.0 . . ? C47 C48 H48A 110.0 . . ? O12 C48 H48B 110.0 . . ? C47 C48 H48B 110.0 . . ? H48A C48 H48B 108.4 . . ? O12 C49 C50 108.8(3) . . ? O12 C49 H49A 109.9 . . ? C50 C49 H49A 109.9 . . ? O12 C49 H49B 109.9 . . ? C50 C49 H49B 109.9 . . ? H49A C49 H49B 108.3 . . ? O7 C50 C49 109.7(3) . . ? O7 C50 H50A 109.7 . . ? C49 C50 H50A 109.7 . . ? O7 C50 H50B 109.7 . . ? C49 C50 H50B 109.7 . . ? H50A C50 H50B 108.2 . . ? O13 C51 C52 109.8(3) . . ? O13 C51 H51A 109.7 . . ? C52 C51 H51A 109.7 . . ? O13 C51 H51B 109.7 . . ? C52 C51 H51B 109.7 . . ? H51A C51 H51B 108.2 . . ? O14 C52 C51 110.0(3) . . ? O14 C52 H52A 109.7 . . ? C51 C52 H52A 109.7 . . ? O14 C52 H52B 109.7 . . ? C51 C52 H52B 109.7 . . ? H52A C52 H52B 108.2 . . ? O14 C53 C54 110.4(3) . . ? O14 C53 H53A 109.6 . . ? C54 C53 H53A 109.6 . . ? O14 C53 H53B 109.6 . . ? C54 C53 H53B 109.6 . . ? H53A C53 H53B 108.1 . . ? O15 C54 C53 109.7(3) . . ? O15 C54 H54A 109.7 . . ? C53 C54 H54A 109.7 . . ? O15 C54 H54B 109.7 . . ? C53 C54 H54B 109.7 . . ? H54A C54 H54B 108.2 . . ? O15 C55 C56 110.2(3) . . ? O15 C55 H55A 109.6 . . ? C56 C55 H55A 109.6 . . ? O15 C55 H55B 109.6 . . ? C56 C55 H55B 109.6 . . ? H55A C55 H55B 108.1 . . ? O16 C56 C55 108.8(3) . . ? O16 C56 H56A 109.9 . . ? C55 C56 H56A 109.9 . . ? O16 C56 H56B 109.9 . . ? C55 C56 H56B 109.9 . . ? H56A C56 H56B 108.3 . . ? O16 C57 C58 110.3(3) . . ? O16 C57 H57A 109.6 . . ? C58 C57 H57A 109.6 . . ? O16 C57 H57B 109.6 . . ? C58 C57 H57B 109.6 . . ? H57A C57 H57B 108.1 . . ? O17 C58 C57 111.6(4) . . ? O17 C58 H58A 109.3 . . ? C57 C58 H58A 109.3 . . ? O17 C58 H58B 109.3 . . ? C57 C58 H58B 109.3 . . ? H58A C58 H58B 108.0 . . ? O17 C59 C60 110.0(4) . . ? O17 C59 H59A 109.7 . . ? C60 C59 H59A 109.7 . . ? O17 C59 H59B 109.7 . . ? C60 C59 H59B 109.7 . . ? H59A C59 H59B 108.2 . . ? O18 C60 C59 109.8(4) . . ? O18 C60 H60A 109.7 . . ? C59 C60 H60A 109.7 . . ? O18 C60 H60B 109.7 . . ? C59 C60 H60B 109.7 . . ? H60A C60 H60B 108.2 . . ? O18 C61 C62 109.5(3) . . ? O18 C61 H61A 109.8 . . ? C62 C61 H61A 109.8 . . ? O18 C61 H61B 109.8 . . ? C62 C61 H61B 109.8 . . ? H61A C61 H61B 108.2 . . ? O13 C62 C61 111.0(3) . . ? O13 C62 H62A 109.4 . . ? C61 C62 H62A 109.4 . . ? O13 C62 H62B 109.4 . . ? C61 C62 H62B 109.4 . . ? H62A C62 H62B 108.0 . . ? O19 C63 C64 109.7(3) . . ? O19 C63 H63A 109.7 . . ? C64 C63 H63A 109.7 . . ? O19 C63 H63B 109.7 . . ? C64 C63 H63B 109.7 . . ? H63A C63 H63B 108.2 . . ? O20 C64 C63 110.2(3) . . ? O20 C64 H64A 109.6 . . ? C63 C64 H64A 109.6 . . ? O20 C64 H64B 109.6 . . ? C63 C64 H64B 109.6 . . ? H64A C64 H64B 108.1 . . ? O20 C65 C66 109.0(3) . . ? O20 C65 H65A 109.9 . . ? C66 C65 H65A 109.9 . . ? O20 C65 H65B 109.9 . . ? C66 C65 H65B 109.9 . . ? H65A C65 H65B 108.3 . . ? O21 C66 C65 108.6(3) . . ? O21 C66 H66A 110.0 . . ? C65 C66 H66A 110.0 . . ? O21 C66 H66B 110.0 . . ? C65 C66 H66B 110.0 . . ? H66A C66 H66B 108.3 . . ? O21 C67 C68 108.9(3) . . ? O21 C67 H67A 109.9 . . ? C68 C67 H67A 109.9 . . ? O21 C67 H67B 109.9 . . ? C68 C67 H67B 109.9 . . ? H67A C67 H67B 108.3 . . ? O22 C68 C67 109.5(3) . . ? O22 C68 H68A 109.8 . . ? C67 C68 H68A 109.8 . . ? O22 C68 H68B 109.8 . . ? C67 C68 H68B 109.8 . . ? H68A C68 H68B 108.2 . . ? O22 C69 C70 109.5(3) . . ? O22 C69 H69A 109.8 . . ? C70 C69 H69A 109.8 . . ? O22 C69 H69B 109.8 . . ? C70 C69 H69B 109.8 . . ? H69A C69 H69B 108.2 . . ? O23 C70 C69 109.3(3) . . ? O23 C70 H70A 109.8 . . ? C69 C70 H70A 109.8 . . ? O23 C70 H70B 109.8 . . ? C69 C70 H70B 109.8 . . ? H70A C70 H70B 108.3 . . ? O23 C71 C72 109.9(3) . . ? O23 C71 H71A 109.7 . . ? C72 C71 H71A 109.7 . . ? O23 C71 H71B 109.7 . . ? C72 C71 H71B 109.7 . . ? H71A C71 H71B 108.2 . . ? O24 C72 C71 108.4(3) . . ? O24 C72 H72A 110.0 . . ? C71 C72 H72A 110.0 . . ? O24 C72 H72B 110.0 . . ? C71 C72 H72B 110.0 . . ? H72A C72 H72B 108.4 . . ? O24 C73 C74 108.4(3) . . ? O24 C73 H73A 110.0 . . ? C74 C73 H73A 110.0 . . ? O24 C73 H73B 110.0 . . ? C74 C73 H73B 110.0 . . ? H73A C73 H73B 108.4 . . ? O19 C74 C73 110.1(3) . . ? O19 C74 H74A 109.6 . . ? C73 C74 H74A 109.6 . . ? O19 C74 H74B 109.6 . . ? C73 C74 H74B 109.6 . . ? H74A C74 H74B 108.2 . . ? C76 C75 H75A 109.5 . . ? C76 C75 H75B 109.5 . . ? H75A C75 H75B 109.5 . . ? C76 C75 H75C 109.5 . . ? H75A C75 H75C 109.5 . . ? H75B C75 H75C 109.5 . . ? N5 C76 C75 179.1(5) . . ? O27 Cl1 O28 110.7(2) . . ? O27 Cl1 O25 110.2(2) . . ? O28 Cl1 O25 110.37(19) . . ? O27 Cl1 O26 109.7(3) . . ? O28 Cl1 O26 108.4(2) . . ? O25 Cl1 O26 107.38(18) . . ? O29 Cl2 O30 111.6(2) . . ? O29 Cl2 O31 110.2(2) . . ? O30 Cl2 O31 109.75(18) . . ? O29 Cl2 O32 108.9(2) . . ? O30 Cl2 O32 108.0(2) . . ? O31 Cl2 O32 108.32(19) . . ? O36 Cl3 O34 109.7(3) . . ? O36 Cl3 O35 109.6(2) . . ? O34 Cl3 O35 109.8(2) . . ? O36 Cl3 O33 109.01(19) . . ? O34 Cl3 O33 109.6(2) . . ? O35 Cl3 O33 109.1(2) . . ? O37 Cl4 O39 110.6(2) . . ? O37 Cl4 O40 109.83(19) . . ? O39 Cl4 O40 109.94(19) . . ? O37 Cl4 O38 108.5(2) . . ? O39 Cl4 O38 108.97(18) . . ? O40 Cl4 O38 108.97(19) . . ? C1 N1 H1NA 106(3) . . ? C1 N1 H1NB 108(3) . . ? H1NA N1 H1NB 114(5) . . ? C1 N1 H1NC 111(3) . . ? H1NA N1 H1NC 107(4) . . ? H1NB N1 H1NC 111(5) . . ? C11 N2 H2NA 107(3) . . ? C11 N2 H2NB 112(4) . . ? H2NA N2 H2NB 115(5) . . ? C11 N2 H2NC 113(3) . . ? H2NA N2 H2NC 112(4) . . ? H2NB N2 H2NC 98(4) . . ? C14 N3 H3NA 106(4) . . ? C14 N3 H3NB 105(4) . . ? H3NA N3 H3NB 111(6) . . ? C14 N3 H3NC 108(3) . . ? H3NA N3 H3NC 111(5) . . ? H3NB N3 H3NC 117(5) . . ? C24 N4 H4NA 110(3) . . ? C24 N4 H4NB 113(4) . . ? H4NA N4 H4NB 102(4) . . ? C24 N4 H4NC 119(4) . . ? H4NA N4 H4NC 108(5) . . ? H4NB N4 H4NC 103(5) . . ? C38 O1 C27 110.5(3) . . ? C29 O2 C28 112.4(3) . . ? C31 O3 C30 112.1(3) . . ? C32 O4 C33 110.7(3) . . ? C35 O5 C34 112.4(3) . . ? C36 O6 C37 111.3(3) . . ? C39 O7 C50 112.8(3) . . ? C41 O8 C40 111.4(3) . . ? C43 O9 C42 112.6(3) . . ? C44 O10 C45 111.0(3) . . ? C47 O11 C46 110.0(3) . . ? C49 O12 C48 112.5(3) . . ? C62 O13 C51 111.6(3) . . ? C53 O14 C52 110.6(3) . . ? C55 O15 C54 112.8(3) . . ? C57 O16 C56 111.1(3) . . ? C58 O17 C59 113.4(3) . . ? C61 O18 C60 111.3(3) . . ? C63 O19 C74 110.9(3) . . ? C65 O20 C64 112.1(3) . . ? C67 O21 C66 112.7(3) . . ? C69 O22 C68 111.2(3) . . ? C70 O23 C71 111.7(3) . . ? C73 O24 C72 111.9(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 C61 H61A O36 0.99 2.58 3.453(5) 146.8 1_655 C41 H41A O30 0.99 2.48 3.322(5) 142.7 2_645 C67 H67B O38 0.99 2.54 3.430(5) 150.2 . C18 H18 O41 0.95 2.59 3.536(4) 174.1 . N4 H4NA O18 0.81(4) 2.06(5) 2.863(4) 171(4) 1_455 N4 H4NC O16 0.82(6) 2.07(6) 2.875(4) 167(5) 1_455 N4 H4NB O14 0.74(5) 2.14(5) 2.840(5) 160(5) 1_455 C28 H28B O38 0.99 2.49 3.412(5) 155.0 3_666 C32 H32A O32 0.99 2.64 3.590(5) 161.0 3_666 N3 H3NC O11 0.98(6) 1.95(6) 2.930(4) 176(5) . N3 H3NA O9 0.68(5) 2.15(6) 2.826(4) 174(6) . N3 H3NB O7 0.71(5) 2.17(6) 2.870(5) 174(5) . N1 H1NC O5 0.85(5) 1.99(5) 2.838(4) 173(4) . N1 H1NB O3 0.76(5) 2.13(5) 2.886(5) 171(5) . N1 H1NA O1 0.89(5) 2.02(5) 2.912(4) 173(4) . N2 H2NC O23 0.85(5) 2.04(5) 2.829(4) 156(4) 1_656 N2 H2NA O21 0.90(5) 2.02(5) 2.916(4) 174(4) 1_656 N2 H2NB O19 0.75(5) 2.11(5) 2.859(4) 175(5) 1_656 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.329 _refine_diff_density_min -0.270 _refine_diff_density_rms 0.093 #END*****************************************************************