Supplementary Material (ESI) for Journal of Materials Chemistry This journal is (C) The Royal Society of Chemistry 2006 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 #============================================================================== _audit_creation_method SHELXL-97 _publ_contact_author_name 'Balasubramanian Viswanathan' _publ_contact_author_address ; Department of Chemistry Indian Institute of Technology Madras Chennai- 600 036 India ; _publ_contact_author_email bvnathan@iitm.ac.in _publ_contact_author_fax 91(44)22578250 _publ_contact_author_phone 91(44)22578250 #============================================================================== # TITLE AND AUTHOR LIST _publ_section_title ; Synthesis and crystal structure of [2+2]calixsalens ; loop_ _publ_author_name _publ_author_address 'Sankareswaran Srimurugan' ; Department of Chemistry Indian Institute of Technology Madras Chennai- 600 036 India ; 'Balasubramanian Viswanathan' ; Department of Chemistry Indian Institute of Technology Madras Chennai- 600 036 India ; 'Thirukkallam Kanthadai Varadarajan' ; Department of Chemistry Indian Institute of Technology Madras Chennai- 600 036 India ; 'Babu Varghese' ; Sophisticated Analytical Instruments Facility Indian Institute of Technology Madras Chennai- 600 036 India ; #============================================================================== data_muru _database_code_depnum_ccdc_archive 'CCDC 296811' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C40 H40 N4 O8 S2), 1.33(C H2 Cl2), 0.66(C2 H6 O), (H2 O)' _chemical_formula_sum 'C42.67 H48.67 Cl2.67 N4 O9.67 S2' _chemical_formula_weight 930.84 _chemical_absolute_configuration ad 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' S S 0.1246 0.1234 '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 C2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 27.55(2) _cell_length_b 10.928(8) _cell_length_c 23.154(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.42(5) _cell_angle_gamma 90.00 _cell_volume 6971(8) _cell_formula_units_Z 6 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10 _cell_measurement_theta_max 15 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.330 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2924 _exptl_absorpt_coefficient_mu 0.326 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_factor_muR 0.000 _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 3 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied. ; _exptl_absorpt_correction_T_min 0.8127 _exptl_absorpt_correction_T_max 0.9968 _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 'cad4 diffractometer' _diffrn_measurement_method 'omega twotheta' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count ? _diffrn_standards_interval_time '1 hour' _diffrn_standards_decay_% 0 _diffrn_reflns_number 7159 _diffrn_reflns_av_R_equivalents 0.0169 _diffrn_reflns_av_sigmaI/netI 0.0873 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 25.01 _reflns_number_total 6480 _reflns_number_gt 3413 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'cad4 system software' _computing_cell_refinement 'cad4 system software' _computing_data_reduction 'XCAD4 (WINGX)' _computing_structure_solution 'XCAD4 (WINGX)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP32 (WINGX)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1808P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.09(3) _refine_ls_number_reflns 6480 _refine_ls_number_parameters 839 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.1477 _refine_ls_R_factor_gt 0.0872 _refine_ls_wR_factor_ref 0.2484 _refine_ls_wR_factor_gt 0.2237 _refine_ls_goodness_of_fit_ref 0.954 _refine_ls_restrained_S_all 0.954 _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 0.3893(3) 0.8552(10) 0.2268(5) 0.059(3) Uani 1 1 d . . . H1 H 0.4119 0.7866 0.2224 0.071 Uiso 1 1 calc R . . C2 C 0.4085(4) 0.9386(12) 0.2733(5) 0.069(3) Uani 1 1 d . . . H2A H 0.3852 1.0038 0.2796 0.083 Uiso 1 1 calc R . . H2B H 0.4115 0.8927 0.3090 0.083 Uiso 1 1 calc R . . C3 C 0.4563(4) 0.9938(14) 0.2595(7) 0.092(4) Uani 1 1 d . . . H3A H 0.4809 0.9303 0.2582 0.110 Uiso 1 1 calc R . . H3B H 0.4654 1.0518 0.2894 0.110 Uiso 1 1 calc R . . C4 C 0.4532(5) 1.0606(13) 0.1997(7) 0.090(4) Uani 1 1 d . . . H4A H 0.4328 1.1327 0.2034 0.109 Uiso 1 1 calc R . . H4B H 0.4854 1.0875 0.1887 0.109 Uiso 1 1 calc R . . C5 C 0.4326(4) 0.9792(14) 0.1525(6) 0.078(4) Uani 1 1 d . . . H5A H 0.4280 1.0273 0.1177 0.094 Uiso 1 1 calc R . . H5B H 0.4558 0.9150 0.1441 0.094 Uiso 1 1 calc R . . C6 C 0.3851(3) 0.9221(9) 0.1688(5) 0.059(3) Uani 1 1 d . . . H6 H 0.3615 0.9884 0.1736 0.070 Uiso 1 1 calc R . . C7 C 0.3219(3) 0.8422(9) 0.1101(5) 0.051(2) Uani 1 1 d . . . H7 H 0.3022 0.9007 0.1273 0.061 Uiso 1 1 calc R . . C8 C 0.2999(3) 0.7594(9) 0.0696(4) 0.050(2) Uani 1 1 d . . . C9 C 0.2500(4) 0.7595(9) 0.0581(5) 0.055(3) Uani 1 1 d . . . H9 H 0.2304 0.8177 0.0757 0.066 Uiso 1 1 calc R . . C10 C 0.2298(4) 0.6777(10) 0.0223(4) 0.055(2) Uani 1 1 d . . . C11 C 0.2578(4) 0.5959(11) -0.0099(5) 0.067(3) Uani 1 1 d . . . H11 H 0.2433 0.5426 -0.0361 0.080 Uiso 1 1 calc R . . C12 C 0.3074(6) 0.5965(13) -0.0016(6) 0.088(4) Uani 1 1 d . . . H12 H 0.3263 0.5440 -0.0236 0.105 Uiso 1 1 calc R . . C13 C 0.3303(4) 0.6742(11) 0.0390(5) 0.062(3) Uani 1 1 d . . . C14 C 0.1412(4) 0.5908(9) 0.0644(5) 0.060(3) Uani 1 1 d . . . C15 C 0.1343(4) 0.6404(10) 0.1196(6) 0.072(3) Uani 1 1 d . . . H15 H 0.1456 0.7190 0.1273 0.087 Uiso 1 1 calc R . . C16 C 0.1113(4) 0.5760(12) 0.1627(6) 0.075(3) Uani 1 1 d . . . H16 H 0.1075 0.6096 0.1993 0.090 Uiso 1 1 calc R . . C17 C 0.0930(4) 0.4538(9) 0.1495(4) 0.052(2) Uani 1 1 d . . . C18 C 0.1017(3) 0.4032(10) 0.0956(5) 0.056(3) Uani 1 1 d . . . C19 C 0.1260(3) 0.4713(9) 0.0533(5) 0.056(3) Uani 1 1 d . . . H19 H 0.1319 0.4364 0.0174 0.067 Uiso 1 1 calc R . . C20 C 0.0841(3) 0.2803(9) 0.0818(4) 0.048(2) Uani 1 1 d . . . H20 H 0.0925 0.2445 0.0468 0.057 Uiso 1 1 calc R . . C21 C 0.0438(3) 0.0955(8) 0.1035(4) 0.049(2) Uani 1 1 d . . . H21 H 0.0614 0.0678 0.0692 0.058 Uiso 1 1 calc R . . C22 C -0.0119(4) 0.0887(11) 0.0907(6) 0.069(3) Uani 1 1 d . . . H22A H -0.0295 0.1207 0.1236 0.083 Uiso 1 1 calc R . . H22B H -0.0196 0.1393 0.0575 0.083 Uiso 1 1 calc R . . C23 C -0.0279(4) -0.0396(12) 0.0792(6) 0.075(3) Uani 1 1 d . . . H23A H -0.0132 -0.0691 0.0439 0.090 Uiso 1 1 calc R . . H23B H -0.0629 -0.0419 0.0741 0.090 Uiso 1 1 calc R . . C24 C -0.0130(4) -0.1223(11) 0.1299(6) 0.073(3) Uani 1 1 d . . . H24A H -0.0303 -0.0971 0.1642 0.088 Uiso 1 1 calc R . . H24B H -0.0222 -0.2060 0.1213 0.088 Uiso 1 1 calc R . . C25 C 0.0410(4) -0.1166(10) 0.1416(6) 0.066(3) Uani 1 1 d . . . H25A H 0.0490 -0.1666 0.1749 0.079 Uiso 1 1 calc R . . H25B H 0.0584 -0.1485 0.1086 0.079 Uiso 1 1 calc R . . C26 C 0.0557(3) 0.0133(9) 0.1526(4) 0.049(2) Uani 1 1 d . . . H26 H 0.0372 0.0422 0.1859 0.059 Uiso 1 1 calc R . . C27 C 0.1209(4) 0.0946(9) 0.2082(5) 0.057(3) Uani 1 1 d . . . H27 H 0.0967 0.1305 0.2304 0.068 Uiso 1 1 calc R . . C28 C 0.1706(3) 0.1237(9) 0.2226(4) 0.046(2) Uani 1 1 d . . . C29 C 0.2088(3) 0.0721(10) 0.1871(5) 0.058(3) Uani 1 1 d . . . C30 C 0.2558(4) 0.1087(10) 0.2024(6) 0.068(3) Uani 1 1 d . . . H30 H 0.2813 0.0814 0.1797 0.081 Uiso 1 1 calc R . . C31 C 0.2666(4) 0.1821(10) 0.2487(6) 0.069(3) Uani 1 1 d . . . H31 H 0.2988 0.2010 0.2569 0.082 Uiso 1 1 calc R . . C32 C 0.2308(3) 0.2279(8) 0.2828(5) 0.050(2) Uani 1 1 d . . . C33 C 0.1812(4) 0.1972(9) 0.2672(5) 0.057(3) Uani 1 1 d . . . H33 H 0.1560 0.2296 0.2888 0.068 Uiso 1 1 calc R . . C34 C 0.2456(4) 0.4737(9) 0.3100(4) 0.052(2) Uani 1 1 d . . . C35 C 0.2018(4) 0.5399(10) 0.3001(5) 0.063(3) Uani 1 1 d . . . H35 H 0.1719 0.5045 0.3080 0.075 Uiso 1 1 calc R . . C36 C 0.2044(4) 0.6582(12) 0.2783(6) 0.074(4) Uani 1 1 d . . . H36 H 0.1760 0.7030 0.2734 0.088 Uiso 1 1 calc R . . C37 C 0.2474(4) 0.7096(10) 0.2640(5) 0.057(3) Uani 1 1 d . . . C38 C 0.2917(3) 0.6437(10) 0.2734(5) 0.058(3) Uani 1 1 d . . . C39 C 0.2874(4) 0.5229(10) 0.2941(5) 0.057(3) Uani 1 1 d . . . H39 H 0.3153 0.4753 0.2968 0.068 Uiso 1 1 calc R . . C40 C 0.3373(3) 0.6963(10) 0.2559(5) 0.058(3) Uani 1 1 d . . . H40 H 0.3646 0.6465 0.2550 0.069 Uiso 1 1 calc R . . C41 C 0.1453(3) 0.9884(10) 0.3822(4) 0.056(3) Uani 1 1 d . . . H41 H 0.1494 1.0729 0.3818 0.067 Uiso 1 1 calc R . . C42 C 0.2260(3) 0.9837(10) 0.4226(4) 0.056(3) Uani 1 1 d . . . H42 H 0.2273 1.0666 0.4066 0.067 Uiso 1 1 calc R . . C43 C 0.2699(4) 0.9118(13) 0.4006(6) 0.079(4) Uani 1 1 d . . . H43A H 0.2694 0.8293 0.4161 0.094 Uiso 1 1 calc R . . H43B H 0.2686 0.9067 0.3588 0.094 Uiso 1 1 calc R . . C44 C 0.3161(4) 0.9757(16) 0.4194(6) 0.089(4) Uani 1 1 d . . . H44A H 0.3440 0.9283 0.4073 0.106 Uiso 1 1 calc R . . H44B H 0.3179 1.0556 0.4013 0.106 Uiso 1 1 calc R . . C45 C 0.3170(4) 0.9900(17) 0.4831(6) 0.094(5) Uani 1 1 d . . . H45A H 0.3465 1.0326 0.4942 0.112 Uiso 1 1 calc R . . H45B H 0.3180 0.9094 0.5007 0.112 Uiso 1 1 calc R . . C46 C 0.2730(4) 1.0607(17) 0.5070(6) 0.090(4) Uani 1 1 d . . . H46A H 0.2731 1.1442 0.4929 0.108 Uiso 1 1 calc R . . H46B H 0.2743 1.0626 0.5489 0.108 Uiso 1 1 calc R . . C47 C 0.2264(3) 0.9925(11) 0.4859(5) 0.063(3) Uani 1 1 d . . . H47 H 0.2258 0.9100 0.5025 0.076 Uiso 1 1 calc R . . C48 C 0.1605(3) 1.0247(9) 0.5492(5) 0.054(2) Uani 1 1 d . . . H48 H 0.1704 0.9547 0.5689 0.065 Uiso 1 1 calc R . . C49 C 0.1175(3) 1.0925(9) 0.5698(4) 0.051(2) Uani 1 1 d . . . C50 C 0.0993(4) 1.1888(9) 0.5371(5) 0.060(3) Uani 1 1 d . . . C51 C 0.0597(5) 1.2510(12) 0.5606(5) 0.074(3) Uani 1 1 d . . . H51 H 0.0488 1.3206 0.5413 0.089 Uiso 1 1 calc R . . C52 C 0.0369(4) 1.2196(10) 0.6071(5) 0.061(3) Uani 1 1 d . . . H52 H 0.0097 1.2628 0.6194 0.073 Uiso 1 1 calc R . . C53 C -0.0544(3) 1.1178(10) 0.3614(4) 0.053(2) Uani 1 1 d . . . C54 C 0.0941(3) 1.0558(9) 0.6196(4) 0.051(2) Uani 1 1 d . . . H54 H 0.1055 0.9885 0.6402 0.062 Uiso 1 1 calc R . . C55 C 0.0208(4) 0.9714(10) 0.3191(4) 0.053(2) Uani 1 1 d . . . C56 C 0.0634(4) 1.0167(9) 0.3420(4) 0.054(3) Uani 1 1 d . . . H56 H 0.0675 1.1011 0.3438 0.065 Uiso 1 1 calc R . . C57 C 0.1016(4) 0.9403(9) 0.3631(5) 0.057(3) Uani 1 1 d . . . C58 C 0.0937(4) 0.8116(10) 0.3573(5) 0.063(3) Uani 1 1 d . . . C59 C 0.0493(5) 0.7669(11) 0.3313(6) 0.079(4) Uani 1 1 d . . . H59 H 0.0448 0.6834 0.3254 0.095 Uiso 1 1 calc R . . C60 C 0.0148(4) 0.8459(11) 0.3156(6) 0.070(3) Uani 1 1 d . . . H60 H -0.0146 0.8154 0.3018 0.084 Uiso 1 1 calc R . . C61 C 0.0917(4) 0.4496(12) 0.4010(5) 0.072(3) Uani 1 1 d . . . H61A H 0.1142 0.5178 0.3992 0.087 Uiso 1 1 calc R . . H61B H 0.1077 0.3832 0.4215 0.087 Uiso 1 1 calc R . . C62 C 0.3031(11) 0.3752(18) 0.1198(10) 0.181(13) Uani 1 1 d . . . H62A H 0.2982 0.2877 0.1157 0.217 Uiso 1 1 calc R . . H62B H 0.3118 0.4077 0.0823 0.217 Uiso 1 1 calc R . . C63A C 0.0654(8) 0.6099(19) 0.5919(11) 0.110(9) Uani 0.68(3) 1 d PD . . C63B C 0.0972(9) 0.719(3) 0.6352(12) 0.047(9) Uani 0.32(3) 1 d PDU . . C64 C 0.0779(8) 0.7419(15) 0.5734(10) 0.165(12) Uani 1 1 d D . . N1 N 0.3663(3) 0.8405(8) 0.1239(4) 0.059(2) Uani 1 1 d . . . N2 N 0.0580(3) 0.2226(7) 0.1165(4) 0.050(2) Uani 1 1 d . . . N3 N 0.1075(3) 0.0239(7) 0.1676(4) 0.050(2) Uani 1 1 d . . . N4 N 0.3415(3) 0.8060(8) 0.2419(4) 0.061(2) Uani 1 1 d . . . N5 N 0.1801(3) 0.9215(8) 0.4004(4) 0.059(2) Uani 1 1 d . . . N6 N 0.1842(3) 1.0601(9) 0.5051(4) 0.064(2) Uani 1 1 d . . . O1 O 0.3773(3) 0.6675(9) 0.0475(4) 0.081(2) Uani 1 1 d . . . H1A H 0.3855 0.7178 0.0719 0.121 Uiso 1 1 calc R . . O2 O 0.1499(3) 0.8037(7) 0.0192(4) 0.080(2) Uani 1 1 d . . . O3 O 0.1568(4) 0.6191(9) -0.0450(4) 0.091(3) Uani 1 1 d . . . O4 O 0.0698(3) 0.3980(8) 0.1900(4) 0.077(2) Uani 1 1 d . . . H4 H 0.0612 0.3304 0.1785 0.115 Uiso 1 1 calc R . . O5 O 0.1995(3) 0.0025(8) 0.1432(3) 0.071(2) Uani 1 1 d . . . H5 H 0.1702 -0.0079 0.1404 0.107 Uiso 1 1 calc R . . O6 O 0.2891(3) 0.3000(8) 0.3624(4) 0.080(2) Uani 1 1 d . . . O7 O 0.2006(3) 0.3224(8) 0.3786(4) 0.082(2) Uani 1 1 d . . . O8 O 0.2483(3) 0.8222(7) 0.2451(4) 0.075(2) Uani 1 1 d . . . H8 H 0.2764 0.8414 0.2376 0.113 Uiso 1 1 calc R . . O9 O 0.1200(3) 1.2280(7) 0.4896(4) 0.082(3) Uani 1 1 d . . . H9A H 0.1439 1.1859 0.4827 0.123 Uiso 1 1 calc R . . O10 O -0.0026(3) 1.1753(8) 0.2731(3) 0.077(2) Uani 1 1 d . . . O11 O -0.0593(3) 1.0013(9) 0.2636(4) 0.080(2) Uani 1 1 d . . . O12 O 0.1287(3) 0.7341(6) 0.3766(4) 0.080(3) Uani 1 1 d . . . H12A H 0.1513 0.7738 0.3903 0.120 Uiso 1 1 calc R . . O13 O 0.0972(7) 0.7657(14) 0.5135(8) 0.175(7) Uani 1 1 d . . . O14 O 0.0000 0.9440(19) 0.5000 0.178(9) Uani 1 2 d S . . S1 S 0.16677(10) 0.6783(3) 0.00920(14) 0.0665(8) Uani 1 1 d . . . S2 S 0.24198(11) 0.3261(3) 0.33929(13) 0.0637(8) Uani 1 1 d . . . S3 S -0.02501(10) 1.0709(3) 0.29754(12) 0.0605(7) Uani 1 1 d . . . Cl1 Cl 0.07678(11) 0.4017(3) 0.33057(15) 0.0784(9) Uani 1 1 d . . . Cl2 Cl 0.03945(15) 0.4943(4) 0.43888(16) 0.1014(12) Uani 1 1 d . . . Cl3 Cl 0.3502(2) 0.4016(10) 0.1683(3) 0.192(3) Uani 1 1 d . . . Cl4 Cl 0.2490(3) 0.4429(7) 0.1423(3) 0.171(3) Uani 1 1 d . . . O15 O -0.0288(5) 0.6750(9) 0.0006(6) 0.053(3) Uani 0.50 1 d P . . O16 O -0.0051(4) 0.4228(7) 0.0109(4) 0.025 Uiso 0.50 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 0.032(5) 0.051(6) 0.095(8) 0.006(6) -0.005(5) -0.011(4) C2 0.061(7) 0.073(8) 0.073(7) 0.008(7) -0.012(5) -0.023(6) C3 0.055(7) 0.083(9) 0.137(13) -0.003(10) -0.036(7) -0.021(7) C4 0.065(7) 0.071(8) 0.135(12) 0.018(9) -0.017(7) -0.028(7) C5 0.057(6) 0.087(9) 0.091(9) 0.034(8) 0.005(6) -0.012(7) C6 0.038(5) 0.043(5) 0.095(8) 0.017(6) -0.004(5) -0.004(4) C7 0.042(6) 0.042(5) 0.070(7) 0.000(5) 0.005(5) 0.000(4) C8 0.043(5) 0.046(5) 0.060(6) 0.003(5) 0.006(4) 0.001(4) C9 0.055(6) 0.028(5) 0.083(7) 0.016(5) 0.008(5) 0.009(4) C10 0.063(6) 0.046(5) 0.054(6) 0.000(5) -0.006(5) -0.006(5) C11 0.078(8) 0.061(7) 0.061(7) -0.018(6) 0.003(5) -0.009(6) C12 0.107(11) 0.067(8) 0.090(9) -0.008(8) 0.043(8) 0.017(8) C13 0.073(7) 0.052(6) 0.060(7) 0.000(6) 0.019(5) 0.003(6) C14 0.046(6) 0.041(6) 0.092(8) 0.004(6) 0.005(5) -0.005(5) C15 0.066(7) 0.033(5) 0.118(11) -0.004(7) -0.012(7) -0.004(5) C16 0.079(8) 0.060(7) 0.087(9) -0.009(7) -0.006(6) 0.009(7) C17 0.057(6) 0.049(6) 0.050(6) 0.005(5) -0.001(5) 0.000(5) C18 0.043(5) 0.049(5) 0.076(7) 0.004(6) -0.004(5) -0.004(5) C19 0.036(5) 0.042(5) 0.090(8) 0.001(6) 0.008(5) -0.002(4) C20 0.044(5) 0.036(5) 0.063(6) -0.003(5) 0.000(4) 0.003(4) C21 0.046(5) 0.039(5) 0.061(6) -0.007(5) 0.007(4) -0.005(4) C22 0.059(7) 0.061(7) 0.087(8) 0.007(7) 0.000(6) -0.002(6) C23 0.056(7) 0.071(8) 0.099(9) 0.004(7) -0.001(6) -0.016(6) C24 0.066(7) 0.053(6) 0.102(10) 0.004(7) 0.014(6) -0.004(6) C25 0.066(7) 0.050(6) 0.083(8) -0.006(6) 0.003(6) -0.006(5) C26 0.037(5) 0.046(5) 0.063(6) 0.004(5) 0.001(4) -0.002(4) C27 0.068(7) 0.044(5) 0.058(6) 0.003(5) 0.016(5) 0.005(5) C28 0.041(5) 0.036(5) 0.061(6) 0.004(5) 0.003(4) 0.008(4) C29 0.052(6) 0.044(5) 0.078(7) -0.017(6) 0.000(5) 0.014(5) C30 0.051(6) 0.049(6) 0.104(9) -0.022(7) 0.005(6) 0.018(5) C31 0.043(6) 0.046(6) 0.116(10) -0.009(7) -0.001(6) 0.009(5) C32 0.050(6) 0.035(5) 0.063(6) 0.014(5) -0.006(5) -0.001(4) C33 0.069(7) 0.043(5) 0.059(6) -0.006(5) 0.017(5) 0.006(5) C34 0.059(6) 0.043(5) 0.055(6) -0.004(5) 0.006(4) -0.022(5) C35 0.054(6) 0.054(6) 0.081(8) 0.016(6) 0.009(5) 0.003(5) C36 0.036(6) 0.075(8) 0.109(10) -0.015(8) 0.005(5) -0.006(6) C37 0.051(6) 0.056(7) 0.063(6) 0.005(5) 0.009(5) -0.001(5) C38 0.042(6) 0.050(6) 0.081(7) 0.006(6) 0.002(5) -0.001(5) C39 0.043(5) 0.046(5) 0.082(7) 0.001(5) 0.003(5) -0.001(5) C40 0.034(5) 0.051(6) 0.088(8) 0.006(6) -0.003(5) -0.008(5) C41 0.056(6) 0.040(5) 0.072(7) 0.008(5) 0.002(5) 0.006(5) C42 0.047(5) 0.055(6) 0.066(6) 0.001(6) 0.013(5) 0.004(5) C43 0.049(6) 0.086(9) 0.101(9) 0.002(8) 0.015(6) 0.016(7) C44 0.057(7) 0.124(12) 0.085(9) 0.031(9) 0.010(6) 0.025(8) C45 0.048(6) 0.132(13) 0.100(10) 0.026(10) -0.015(6) 0.034(8) C46 0.044(6) 0.136(13) 0.091(9) 0.010(10) -0.007(6) -0.002(8) C47 0.053(6) 0.069(7) 0.067(7) 0.007(6) 0.014(5) 0.016(6) C48 0.043(5) 0.045(5) 0.074(7) 0.012(5) -0.001(5) 0.000(5) C49 0.057(6) 0.045(5) 0.051(5) 0.004(5) 0.010(4) -0.002(5) C50 0.053(6) 0.039(5) 0.088(8) 0.008(6) 0.012(5) -0.006(5) C51 0.083(8) 0.063(7) 0.075(8) 0.017(7) 0.021(6) 0.023(7) C52 0.053(6) 0.055(6) 0.074(7) 0.010(6) 0.004(5) 0.008(5) C53 0.047(5) 0.055(6) 0.057(6) -0.003(5) 0.003(4) 0.004(5) C54 0.052(5) 0.049(5) 0.053(6) 0.011(5) -0.004(4) -0.002(5) C55 0.054(6) 0.046(6) 0.059(6) 0.002(5) 0.005(5) -0.003(5) C56 0.063(6) 0.037(5) 0.062(6) 0.008(5) 0.009(5) 0.005(5) C57 0.060(7) 0.048(6) 0.065(7) -0.003(5) 0.000(5) 0.005(5) C58 0.060(7) 0.048(6) 0.080(8) 0.011(6) 0.019(6) 0.013(6) C59 0.081(9) 0.048(6) 0.108(10) -0.014(7) 0.010(7) -0.018(6) C60 0.044(6) 0.057(7) 0.110(10) -0.007(7) -0.001(6) -0.001(5) C61 0.078(8) 0.073(8) 0.066(7) 0.020(7) -0.010(6) -0.007(6) C62 0.34(4) 0.084(12) 0.122(16) 0.026(12) 0.10(2) 0.042(18) C63A 0.077(14) 0.13(2) 0.13(2) -0.005(17) 0.018(13) -0.013(14) C63B 0.038(12) 0.036(12) 0.069(13) 0.015(9) 0.015(8) 0.010(8) C64 0.17(2) 0.097(14) 0.23(3) -0.085(17) 0.10(2) -0.028(14) N1 0.040(5) 0.058(5) 0.080(6) 0.011(5) 0.002(4) -0.008(4) N2 0.050(5) 0.038(4) 0.063(5) 0.013(4) -0.001(4) -0.004(4) N3 0.057(5) 0.037(4) 0.056(5) 0.001(4) -0.005(4) 0.004(4) N4 0.038(4) 0.062(6) 0.082(6) 0.024(5) 0.005(4) -0.007(4) N5 0.051(5) 0.044(5) 0.084(6) 0.010(5) 0.006(4) 0.006(4) N6 0.046(5) 0.061(5) 0.083(6) 0.022(5) 0.011(4) 0.008(4) O1 0.050(4) 0.102(6) 0.090(6) -0.005(6) 0.016(4) 0.023(5) O2 0.058(4) 0.061(5) 0.120(7) 0.020(5) -0.024(4) -0.013(4) O3 0.126(7) 0.077(5) 0.068(5) 0.013(5) -0.032(5) -0.029(5) O4 0.072(5) 0.066(5) 0.092(6) -0.005(5) 0.019(4) -0.016(4) O5 0.061(4) 0.070(5) 0.082(5) -0.040(5) 0.005(4) 0.015(4) O6 0.082(5) 0.063(5) 0.096(6) 0.026(5) -0.023(4) -0.017(4) O7 0.100(6) 0.069(5) 0.077(5) 0.001(5) 0.025(5) -0.031(5) O8 0.053(4) 0.047(4) 0.125(7) 0.027(5) 0.009(4) 0.001(4) O9 0.069(5) 0.062(5) 0.116(7) 0.037(5) 0.032(5) 0.009(4) O10 0.080(5) 0.078(5) 0.072(5) 0.020(5) 0.014(4) 0.020(5) O11 0.067(5) 0.097(6) 0.077(5) -0.010(5) -0.006(4) 0.011(5) O12 0.062(5) 0.034(4) 0.144(8) 0.010(5) 0.002(5) 0.006(3) O13 0.231(17) 0.104(9) 0.188(16) 0.022(11) -0.046(13) -0.071(11) O14 0.29(3) 0.097(13) 0.152(17) 0.000 -0.040(17) 0.000 S1 0.0657(17) 0.0489(15) 0.085(2) 0.0159(16) -0.0158(14) -0.0151(14) S2 0.0774(19) 0.0510(15) 0.0626(17) 0.0076(14) -0.0021(14) -0.0178(14) S3 0.0573(15) 0.0663(17) 0.0579(15) -0.0022(15) 0.0012(12) 0.0118(14) Cl1 0.0670(18) 0.083(2) 0.085(2) -0.0145(19) -0.0009(14) -0.0043(16) Cl2 0.130(3) 0.080(2) 0.095(2) -0.003(2) 0.041(2) -0.006(2) Cl3 0.141(4) 0.275(9) 0.161(5) -0.036(7) 0.037(4) -0.043(6) Cl4 0.199(6) 0.169(6) 0.146(5) 0.016(5) -0.016(4) 0.039(5) O15 0.073(8) 0.003(4) 0.083(9) 0.002(6) -0.025(7) -0.009(5) _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 N4 1.467(12) . ? C1 C2 1.503(16) . ? C1 C6 1.533(15) . ? C1 H1 0.9800 . ? C2 C3 1.485(16) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.57(2) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.51(2) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.501(14) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 N1 1.461(14) . ? C6 H6 0.9800 . ? C7 N1 1.262(12) . ? C7 C8 1.434(14) . ? C7 H7 0.9300 . ? C8 C9 1.400(13) . ? C8 C13 1.441(14) . ? C9 C10 1.337(15) . ? C9 H9 0.9300 . ? C10 C11 1.399(15) . ? C10 S1 1.760(11) . ? C11 C12 1.378(18) . ? C11 H11 0.9300 . ? C12 C13 1.413(19) . ? C12 H12 0.9300 . ? C13 O1 1.310(13) . ? C14 C19 1.395(15) . ? C14 C15 1.401(17) . ? C14 S1 1.749(11) . ? C15 C16 1.380(18) . ? C15 H15 0.9300 . ? C16 C17 1.458(16) . ? C16 H16 0.9300 . ? C17 O4 1.292(12) . ? C17 C18 1.386(15) . ? C18 C19 1.405(15) . ? C18 C20 1.463(14) . ? C19 H19 0.9300 . ? C20 N2 1.253(12) . ? C20 H20 0.9300 . ? C21 N2 1.473(12) . ? C21 C26 1.484(14) . ? C21 C22 1.562(14) . ? C21 H21 0.9800 . ? C22 C23 1.493(17) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.535(18) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 C25 1.512(16) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 C26 1.498(15) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 N3 1.471(12) . ? C26 H26 0.9800 . ? C27 N3 1.270(13) . ? C27 C28 1.444(14) . ? C27 H27 0.9300 . ? C28 C33 1.339(14) . ? C28 C29 1.454(13) . ? C29 O5 1.293(12) . ? C29 C30 1.397(15) . ? C30 C31 1.370(16) . ? C30 H30 0.9300 . ? C31 C32 1.364(14) . ? C31 H31 0.9300 . ? C32 C33 1.451(15) . ? C32 S2 1.718(11) . ? C33 H33 0.9300 . ? C34 C39 1.325(13) . ? C34 C35 1.425(15) . ? C34 S2 1.752(10) . ? C35 C36 1.389(17) . ? C35 H35 0.9300 . ? C36 C37 1.354(15) . ? C36 H36 0.9300 . ? C37 O8 1.307(13) . ? C37 C38 1.434(15) . ? C38 C39 1.409(15) . ? C38 C40 1.441(13) . ? C39 H39 0.9300 . ? C40 N4 1.247(14) . ? C40 H40 0.9300 . ? C41 N5 1.276(12) . ? C41 C57 1.383(15) . ? C41 H41 0.9300 . ? C42 C47 1.467(14) . ? C42 N5 1.522(14) . ? C42 C43 1.533(14) . ? C42 H42 0.9800 . ? C43 C44 1.513(19) . ? C43 H43A 0.9700 . ? C43 H43B 0.9700 . ? C44 C45 1.482(18) . ? C44 H44A 0.9700 . ? C44 H44B 0.9700 . ? C45 C46 1.544(18) . ? C45 H45A 0.9700 . ? C45 H45B 0.9700 . ? C46 C47 1.562(16) . ? C46 H46A 0.9700 . ? C46 H46B 0.9700 . ? C47 N6 1.450(13) . ? C47 H47 0.9800 . ? C48 N6 1.277(13) . ? C48 C49 1.478(13) . ? C48 H48 0.9300 . ? C49 C54 1.387(13) . ? C49 C50 1.387(14) . ? C50 O9 1.315(14) . ? C50 C51 1.400(15) . ? C51 C52 1.297(15) . ? C51 H51 0.9300 . ? C52 C53 1.414(15) 2_556 ? C52 H52 0.9300 . ? C53 C54 1.362(14) 2_556 ? C53 C52 1.414(15) 2_556 ? C53 S3 1.767(10) . ? C54 C53 1.362(14) 2_556 ? C54 H54 0.9300 . ? C55 C56 1.378(15) . ? C55 C60 1.383(16) . ? C55 S3 1.736(11) . ? C56 C57 1.427(15) . ? C56 H56 0.9300 . ? C57 C58 1.429(16) . ? C58 O12 1.358(13) . ? C58 C59 1.445(17) . ? C59 C60 1.332(17) . ? C59 H59 0.9300 . ? C60 H60 0.9300 . ? C61 Cl1 1.760(13) . ? C61 Cl2 1.760(13) . ? C61 H61A 0.9700 . ? C61 H61B 0.9700 . ? C62 Cl3 1.73(3) . ? C62 Cl4 1.75(2) . ? C62 H62A 0.9700 . ? C62 H62B 0.9700 . ? C63A C64 1.543(10) . ? C63A C63B 1.78(4) . ? C63B C64 1.543(10) . ? C64 O13 1.51(2) . ? O1 H1A 0.8200 . ? O2 S1 1.465(9) . ? O3 S1 1.436(9) . ? O4 H4 0.8200 . ? O5 H5 0.8200 . ? O6 S2 1.430(8) . ? O7 S2 1.464(8) . ? O8 H8 0.8200 . ? O9 H9A 0.8200 . ? O10 S3 1.417(9) . ? O11 S3 1.442(9) . ? O12 H12A 0.8200 . ? O15 O15 1.59(3) 2 ? O16 O16 0.578(14) 2 ? 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 N4 C1 C2 111.4(9) . . ? N4 C1 C6 108.7(8) . . ? C2 C1 C6 111.2(9) . . ? N4 C1 H1 108.5 . . ? C2 C1 H1 108.5 . . ? C6 C1 H1 108.5 . . ? C3 C2 C1 113.6(10) . . ? C3 C2 H2A 108.8 . . ? C1 C2 H2A 108.8 . . ? C3 C2 H2B 108.8 . . ? C1 C2 H2B 108.8 . . ? H2A C2 H2B 107.7 . . ? C2 C3 C4 109.6(10) . . ? C2 C3 H3A 109.8 . . ? C4 C3 H3A 109.8 . . ? C2 C3 H3B 109.8 . . ? C4 C3 H3B 109.8 . . ? H3A C3 H3B 108.2 . . ? C5 C4 C3 112.4(11) . . ? C5 C4 H4A 109.1 . . ? C3 C4 H4A 109.1 . . ? C5 C4 H4B 109.1 . . ? C3 C4 H4B 109.1 . . ? H4A C4 H4B 107.9 . . ? C6 C5 C4 112.7(11) . . ? C6 C5 H5A 109.0 . . ? C4 C5 H5A 109.0 . . ? C6 C5 H5B 109.0 . . ? C4 C5 H5B 109.0 . . ? H5A C5 H5B 107.8 . . ? N1 C6 C5 112.4(10) . . ? N1 C6 C1 110.9(8) . . ? C5 C6 C1 111.0(9) . . ? N1 C6 H6 107.4 . . ? C5 C6 H6 107.4 . . ? C1 C6 H6 107.4 . . ? N1 C7 C8 124.1(9) . . ? N1 C7 H7 118.0 . . ? C8 C7 H7 118.0 . . ? C9 C8 C7 122.2(9) . . ? C9 C8 C13 118.7(10) . . ? C7 C8 C13 119.0(9) . . ? C10 C9 C8 121.4(9) . . ? C10 C9 H9 119.3 . . ? C8 C9 H9 119.3 . . ? C9 C10 C11 121.9(10) . . ? C9 C10 S1 120.6(8) . . ? C11 C10 S1 117.2(8) . . ? C12 C11 C10 118.2(11) . . ? C12 C11 H11 120.9 . . ? C10 C11 H11 120.9 . . ? C11 C12 C13 122.2(10) . . ? C11 C12 H12 118.9 . . ? C13 C12 H12 118.9 . . ? O1 C13 C12 120.2(10) . . ? O1 C13 C8 122.6(11) . . ? C12 C13 C8 117.2(11) . . ? C19 C14 C15 119.3(10) . . ? C19 C14 S1 119.9(10) . . ? C15 C14 S1 120.8(8) . . ? C16 C15 C14 121.8(10) . . ? C16 C15 H15 119.1 . . ? C14 C15 H15 119.1 . . ? C15 C16 C17 118.4(11) . . ? C15 C16 H16 120.8 . . ? C17 C16 H16 120.8 . . ? O4 C17 C18 123.7(9) . . ? O4 C17 C16 116.9(10) . . ? C18 C17 C16 119.5(10) . . ? C17 C18 C19 120.2(10) . . ? C17 C18 C20 120.3(10) . . ? C19 C18 C20 119.5(10) . . ? C14 C19 C18 120.7(11) . . ? C14 C19 H19 119.7 . . ? C18 C19 H19 119.7 . . ? N2 C20 C18 120.9(9) . . ? N2 C20 H20 119.6 . . ? C18 C20 H20 119.6 . . ? N2 C21 C26 110.9(8) . . ? N2 C21 C22 110.0(8) . . ? C26 C21 C22 109.0(8) . . ? N2 C21 H21 108.9 . . ? C26 C21 H21 108.9 . . ? C22 C21 H21 108.9 . . ? C23 C22 C21 111.6(9) . . ? C23 C22 H22A 109.3 . . ? C21 C22 H22A 109.3 . . ? C23 C22 H22B 109.3 . . ? C21 C22 H22B 109.3 . . ? H22A C22 H22B 108.0 . . ? C22 C23 C24 109.8(11) . . ? C22 C23 H23A 109.7 . . ? C24 C23 H23A 109.7 . . ? C22 C23 H23B 109.7 . . ? C24 C23 H23B 109.7 . . ? H23A C23 H23B 108.2 . . ? C25 C24 C23 111.7(10) . . ? C25 C24 H24A 109.3 . . ? C23 C24 H24A 109.3 . . ? C25 C24 H24B 109.3 . . ? C23 C24 H24B 109.3 . . ? H24A C24 H24B 107.9 . . ? C26 C25 C24 109.5(9) . . ? C26 C25 H25A 109.8 . . ? C24 C25 H25A 109.8 . . ? C26 C25 H25B 109.8 . . ? C24 C25 H25B 109.8 . . ? H25A C25 H25B 108.2 . . ? N3 C26 C21 110.0(7) . . ? N3 C26 C25 112.1(8) . . ? C21 C26 C25 112.7(9) . . ? N3 C26 H26 107.3 . . ? C21 C26 H26 107.3 . . ? C25 C26 H26 107.3 . . ? N3 C27 C28 125.1(9) . . ? N3 C27 H27 117.4 . . ? C28 C27 H27 117.4 . . ? C33 C28 C27 120.7(9) . . ? C33 C28 C29 120.9(9) . . ? C27 C28 C29 118.3(9) . . ? O5 C29 C30 123.0(9) . . ? O5 C29 C28 122.2(9) . . ? C30 C29 C28 114.7(10) . . ? C31 C30 C29 124.2(10) . . ? C31 C30 H30 117.9 . . ? C29 C30 H30 117.9 . . ? C32 C31 C30 120.9(10) . . ? C32 C31 H31 119.5 . . ? C30 C31 H31 119.5 . . ? C31 C32 C33 117.0(10) . . ? C31 C32 S2 123.0(8) . . ? C33 C32 S2 119.8(7) . . ? C28 C33 C32 122.1(9) . . ? C28 C33 H33 119.0 . . ? C32 C33 H33 119.0 . . ? C39 C34 C35 119.0(10) . . ? C39 C34 S2 122.2(9) . . ? C35 C34 S2 118.7(7) . . ? C36 C35 C34 119.1(10) . . ? C36 C35 H35 120.5 . . ? C34 C35 H35 120.5 . . ? C37 C36 C35 121.5(11) . . ? C37 C36 H36 119.3 . . ? C35 C36 H36 119.3 . . ? O8 C37 C36 119.5(11) . . ? O8 C37 C38 120.3(9) . . ? C36 C37 C38 120.0(10) . . ? C39 C38 C37 116.6(9) . . ? C39 C38 C40 123.1(9) . . ? C37 C38 C40 120.0(9) . . ? C34 C39 C38 123.5(10) . . ? C34 C39 H39 118.3 . . ? C38 C39 H39 118.3 . . ? N4 C40 C38 122.6(10) . . ? N4 C40 H40 118.7 . . ? C38 C40 H40 118.7 . . ? N5 C41 C57 122.5(10) . . ? N5 C41 H41 118.7 . . ? C57 C41 H41 118.7 . . ? C47 C42 N5 111.5(8) . . ? C47 C42 C43 111.4(9) . . ? N5 C42 C43 108.3(9) . . ? C47 C42 H42 108.5 . . ? N5 C42 H42 108.5 . . ? C43 C42 H42 108.5 . . ? C44 C43 C42 109.4(11) . . ? C44 C43 H43A 109.8 . . ? C42 C43 H43A 109.8 . . ? C44 C43 H43B 109.8 . . ? C42 C43 H43B 109.8 . . ? H43A C43 H43B 108.2 . . ? C45 C44 C43 110.1(11) . . ? C45 C44 H44A 109.6 . . ? C43 C44 H44A 109.6 . . ? C45 C44 H44B 109.6 . . ? C43 C44 H44B 109.6 . . ? H44A C44 H44B 108.2 . . ? C44 C45 C46 113.6(10) . . ? C44 C45 H45A 108.8 . . ? C46 C45 H45A 108.8 . . ? C44 C45 H45B 108.8 . . ? C46 C45 H45B 108.8 . . ? H45A C45 H45B 107.7 . . ? C45 C46 C47 107.2(12) . . ? C45 C46 H46A 110.3 . . ? C47 C46 H46A 110.3 . . ? C45 C46 H46B 110.3 . . ? C47 C46 H46B 110.3 . . ? H46A C46 H46B 108.5 . . ? N6 C47 C42 109.8(9) . . ? N6 C47 C46 108.7(10) . . ? C42 C47 C46 110.1(8) . . ? N6 C47 H47 109.4 . . ? C42 C47 H47 109.4 . . ? C46 C47 H47 109.4 . . ? N6 C48 C49 121.4(9) . . ? N6 C48 H48 119.3 . . ? C49 C48 H48 119.3 . . ? C54 C49 C50 120.3(9) . . ? C54 C49 C48 120.1(9) . . ? C50 C49 C48 119.5(8) . . ? O9 C50 C49 123.1(9) . . ? O9 C50 C51 120.7(10) . . ? C49 C50 C51 115.9(10) . . ? C52 C51 C50 125.3(11) . . ? C52 C51 H51 117.3 . . ? C50 C51 H51 117.3 . . ? C51 C52 C53 118.1(10) . 2_556 ? C51 C52 H52 121.0 . . ? C53 C52 H52 121.0 2_556 . ? C54 C53 C52 119.8(9) 2_556 2_556 ? C54 C53 S3 120.0(8) 2_556 . ? C52 C53 S3 120.2(8) 2_556 . ? C53 C54 C49 120.3(9) 2_556 . ? C53 C54 H54 119.8 2_556 . ? C49 C54 H54 119.8 . . ? C56 C55 C60 118.7(11) . . ? C56 C55 S3 120.1(8) . . ? C60 C55 S3 121.2(9) . . ? C55 C56 C57 123.1(9) . . ? C55 C56 H56 118.4 . . ? C57 C56 H56 118.4 . . ? C41 C57 C56 121.6(9) . . ? C41 C57 C58 122.5(10) . . ? C56 C57 C58 115.6(10) . . ? O12 C58 C57 118.3(11) . . ? O12 C58 C59 121.7(10) . . ? C57 C58 C59 120.0(10) . . ? C60 C59 C58 119.6(11) . . ? C60 C59 H59 120.2 . . ? C58 C59 H59 120.2 . . ? C59 C60 C55 122.9(11) . . ? C59 C60 H60 118.6 . . ? C55 C60 H60 118.6 . . ? Cl1 C61 Cl2 110.9(7) . . ? Cl1 C61 H61A 109.5 . . ? Cl2 C61 H61A 109.5 . . ? Cl1 C61 H61B 109.5 . . ? Cl2 C61 H61B 109.5 . . ? H61A C61 H61B 108.0 . . ? Cl3 C62 Cl4 111.8(12) . . ? Cl3 C62 H62A 109.3 . . ? Cl4 C62 H62A 109.3 . . ? Cl3 C62 H62B 109.3 . . ? Cl4 C62 H62B 109.3 . . ? H62A C62 H62B 107.9 . . ? C64 C63A C63B 54.7(10) . . ? C64 C63B C63A 54.7(11) . . ? O13 C64 C63B 139(2) . . ? O13 C64 C63A 119.7(16) . . ? C63B C64 C63A 71(2) . . ? C7 N1 C6 120.6(9) . . ? C20 N2 C21 119.7(8) . . ? C27 N3 C26 119.9(8) . . ? C40 N4 C1 119.9(9) . . ? C41 N5 C42 118.4(9) . . ? C48 N6 C47 120.4(9) . . ? C13 O1 H1A 109.5 . . ? C17 O4 H4 109.5 . . ? C29 O5 H5 109.5 . . ? C37 O8 H8 109.5 . . ? C50 O9 H9A 109.5 . . ? C58 O12 H12A 109.5 . . ? O3 S1 O2 120.0(6) . . ? O3 S1 C14 108.5(5) . . ? O2 S1 C14 105.4(6) . . ? O3 S1 C10 109.3(6) . . ? O2 S1 C10 106.8(5) . . ? C14 S1 C10 105.9(5) . . ? O6 S2 O7 118.1(6) . . ? O6 S2 C32 108.5(5) . . ? O7 S2 C32 108.7(5) . . ? O6 S2 C34 105.9(5) . . ? O7 S2 C34 108.2(5) . . ? C32 S2 C34 106.9(5) . . ? O10 S3 O11 119.5(6) . . ? O10 S3 C55 107.5(5) . . ? O11 S3 C55 107.4(5) . . ? O10 S3 C53 107.7(5) . . ? O11 S3 C53 107.8(5) . . ? C55 S3 C53 106.2(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N4 C1 C2 C3 -178.4(10) . . . . ? C6 C1 C2 C3 -57.0(13) . . . . ? C1 C2 C3 C4 54.5(16) . . . . ? C2 C3 C4 C5 -51.8(16) . . . . ? C3 C4 C5 C6 52.4(15) . . . . ? C4 C5 C6 N1 -178.1(10) . . . . ? C4 C5 C6 C1 -53.3(14) . . . . ? N4 C1 C6 N1 -56.9(11) . . . . ? C2 C1 C6 N1 -179.8(8) . . . . ? N4 C1 C6 C5 177.4(10) . . . . ? C2 C1 C6 C5 54.5(13) . . . . ? N1 C7 C8 C9 176.0(10) . . . . ? N1 C7 C8 C13 -4.8(15) . . . . ? C7 C8 C9 C10 -176.6(9) . . . . ? C13 C8 C9 C10 4.2(15) . . . . ? C8 C9 C10 C11 -6.5(16) . . . . ? C8 C9 C10 S1 179.2(8) . . . . ? C9 C10 C11 C12 3.5(17) . . . . ? S1 C10 C11 C12 178.0(10) . . . . ? C10 C11 C12 C13 1.7(19) . . . . ? C11 C12 C13 O1 176.6(12) . . . . ? C11 C12 C13 C8 -3.6(18) . . . . ? C9 C8 C13 O1 -179.5(10) . . . . ? C7 C8 C13 O1 1.3(15) . . . . ? C9 C8 C13 C12 0.8(15) . . . . ? C7 C8 C13 C12 -178.4(10) . . . . ? C19 C14 C15 C16 -2.5(17) . . . . ? S1 C14 C15 C16 175.6(9) . . . . ? C14 C15 C16 C17 -1.1(17) . . . . ? C15 C16 C17 O4 -177.2(11) . . . . ? C15 C16 C17 C18 3.8(16) . . . . ? O4 C17 C18 C19 178.2(10) . . . . ? C16 C17 C18 C19 -3.0(15) . . . . ? O4 C17 C18 C20 0.5(16) . . . . ? C16 C17 C18 C20 179.3(9) . . . . ? C15 C14 C19 C18 3.4(15) . . . . ? S1 C14 C19 C18 -174.7(8) . . . . ? C17 C18 C19 C14 -0.6(15) . . . . ? C20 C18 C19 C14 177.1(9) . . . . ? C17 C18 C20 N2 5.3(14) . . . . ? C19 C18 C20 N2 -172.4(9) . . . . ? N2 C21 C22 C23 -178.2(10) . . . . ? C26 C21 C22 C23 -56.3(13) . . . . ? C21 C22 C23 C24 55.4(14) . . . . ? C22 C23 C24 C25 -56.3(14) . . . . ? C23 C24 C25 C26 56.7(14) . . . . ? N2 C21 C26 N3 -55.3(10) . . . . ? C22 C21 C26 N3 -176.6(8) . . . . ? N2 C21 C26 C25 178.9(8) . . . . ? C22 C21 C26 C25 57.6(11) . . . . ? C24 C25 C26 N3 176.7(9) . . . . ? C24 C25 C26 C21 -58.7(13) . . . . ? N3 C27 C28 C33 -178.4(10) . . . . ? N3 C27 C28 C29 2.2(15) . . . . ? C33 C28 C29 O5 -178.9(10) . . . . ? C27 C28 C29 O5 0.5(15) . . . . ? C33 C28 C29 C30 -1.9(14) . . . . ? C27 C28 C29 C30 177.5(10) . . . . ? O5 C29 C30 C31 -179.8(12) . . . . ? C28 C29 C30 C31 3.2(17) . . . . ? C29 C30 C31 C32 -1.7(19) . . . . ? C30 C31 C32 C33 -1.2(16) . . . . ? C30 C31 C32 S2 -176.8(9) . . . . ? C27 C28 C33 C32 179.8(10) . . . . ? C29 C28 C33 C32 -0.8(15) . . . . ? C31 C32 C33 C28 2.4(15) . . . . ? S2 C32 C33 C28 178.2(8) . . . . ? C39 C34 C35 C36 -5.2(17) . . . . ? S2 C34 C35 C36 178.3(9) . . . . ? C34 C35 C36 C37 2.9(19) . . . . ? C35 C36 C37 O8 -178.3(12) . . . . ? C35 C36 C37 C38 -2.5(18) . . . . ? O8 C37 C38 C39 179.8(11) . . . . ? C36 C37 C38 C39 4.0(17) . . . . ? O8 C37 C38 C40 -6.9(17) . . . . ? C36 C37 C38 C40 177.3(11) . . . . ? C35 C34 C39 C38 7.2(17) . . . . ? S2 C34 C39 C38 -176.4(9) . . . . ? C37 C38 C39 C34 -6.6(17) . . . . ? C40 C38 C39 C34 -179.7(11) . . . . ? C39 C38 C40 N4 -174.3(12) . . . . ? C37 C38 C40 N4 12.8(18) . . . . ? C47 C42 C43 C44 -60.0(14) . . . . ? N5 C42 C43 C44 176.9(10) . . . . ? C42 C43 C44 C45 56.4(16) . . . . ? C43 C44 C45 C46 -57.3(19) . . . . ? C44 C45 C46 C47 56.1(17) . . . . ? N5 C42 C47 N6 -58.4(13) . . . . ? C43 C42 C47 N6 -179.5(10) . . . . ? N5 C42 C47 C46 -178.1(9) . . . . ? C43 C42 C47 C46 60.8(14) . . . . ? C45 C46 C47 N6 -177.1(11) . . . . ? C45 C46 C47 C42 -56.7(14) . . . . ? N6 C48 C49 C54 -176.5(11) . . . . ? N6 C48 C49 C50 7.1(15) . . . . ? C54 C49 C50 O9 179.8(11) . . . . ? C48 C49 C50 O9 -3.8(16) . . . . ? C54 C49 C50 C51 5.8(15) . . . . ? C48 C49 C50 C51 -177.8(11) . . . . ? O9 C50 C51 C52 179.9(13) . . . . ? C49 C50 C51 C52 -6(2) . . . . ? C50 C51 C52 C53 3(2) . . . 2_556 ? C50 C49 C54 C53 -3.4(15) . . . 2_556 ? C48 C49 C54 C53 -179.8(9) . . . 2_556 ? C60 C55 C56 C57 -0.8(17) . . . . ? S3 C55 C56 C57 176.9(8) . . . . ? N5 C41 C57 C56 -178.9(10) . . . . ? N5 C41 C57 C58 -5.8(17) . . . . ? C55 C56 C57 C41 175.5(10) . . . . ? C55 C56 C57 C58 1.9(16) . . . . ? C41 C57 C58 O12 6.5(17) . . . . ? C56 C57 C58 O12 -180.0(9) . . . . ? C41 C57 C58 C59 -173.2(10) . . . . ? C56 C57 C58 C59 0.3(16) . . . . ? O12 C58 C59 C60 176.5(11) . . . . ? C57 C58 C59 C60 -3.7(18) . . . . ? C58 C59 C60 C55 5(2) . . . . ? C56 C55 C60 C59 -3(2) . . . . ? S3 C55 C60 C59 179.4(10) . . . . ? C63A C63B C64 O13 -113(3) . . . . ? C63B C63A C64 O13 136(3) . . . . ? C8 C7 N1 C6 -175.4(9) . . . . ? C5 C6 N1 C7 -137.0(11) . . . . ? C1 C6 N1 C7 98.2(11) . . . . ? C18 C20 N2 C21 -175.4(8) . . . . ? C26 C21 N2 C20 127.6(9) . . . . ? C22 C21 N2 C20 -111.7(10) . . . . ? C28 C27 N3 C26 -172.4(9) . . . . ? C21 C26 N3 C27 96.4(10) . . . . ? C25 C26 N3 C27 -137.5(10) . . . . ? C38 C40 N4 C1 177.4(10) . . . . ? C2 C1 N4 C40 -107.8(13) . . . . ? C6 C1 N4 C40 129.3(12) . . . . ? C57 C41 N5 C42 -177.6(9) . . . . ? C47 C42 N5 C41 98.2(12) . . . . ? C43 C42 N5 C41 -138.8(10) . . . . ? C49 C48 N6 C47 179.6(10) . . . . ? C42 C47 N6 C48 138.5(11) . . . . ? C46 C47 N6 C48 -101.0(12) . . . . ? C19 C14 S1 O3 14.4(10) . . . . ? C15 C14 S1 O3 -163.7(9) . . . . ? C19 C14 S1 O2 144.1(8) . . . . ? C15 C14 S1 O2 -34.0(10) . . . . ? C19 C14 S1 C10 -102.9(9) . . . . ? C15 C14 S1 C10 79.0(10) . . . . ? C9 C10 S1 O3 157.4(9) . . . . ? C11 C10 S1 O3 -17.2(10) . . . . ? C9 C10 S1 O2 26.2(10) . . . . ? C11 C10 S1 O2 -148.5(9) . . . . ? C9 C10 S1 C14 -85.9(10) . . . . ? C11 C10 S1 C14 99.5(9) . . . . ? C31 C32 S2 O6 -30.2(10) . . . . ? C33 C32 S2 O6 154.3(8) . . . . ? C31 C32 S2 O7 -159.7(9) . . . . ? C33 C32 S2 O7 24.7(9) . . . . ? C31 C32 S2 C34 83.7(10) . . . . ? C33 C32 S2 C34 -91.9(8) . . . . ? C39 C34 S2 O6 22.9(10) . . . . ? C35 C34 S2 O6 -160.7(9) . . . . ? C39 C34 S2 O7 150.4(9) . . . . ? C35 C34 S2 O7 -33.2(10) . . . . ? C39 C34 S2 C32 -92.7(10) . . . . ? C35 C34 S2 C32 83.7(9) . . . . ? C56 C55 S3 O10 37.0(10) . . . . ? C60 C55 S3 O10 -145.4(10) . . . . ? C56 C55 S3 O11 166.8(8) . . . . ? C60 C55 S3 O11 -15.5(12) . . . . ? C56 C55 S3 C53 -78.1(9) . . . . ? C60 C55 S3 C53 99.5(11) . . . . ? C54 C53 S3 O10 152.3(8) 2_556 . . . ? C52 C53 S3 O10 -27.8(10) 2_556 . . . ? C54 C53 S3 O11 22.1(10) 2_556 . . . ? C52 C53 S3 O11 -158.0(8) 2_556 . . . ? C54 C53 S3 C55 -92.7(9) 2_556 . . . ? C52 C53 S3 C55 87.2(9) 2_556 . . . ? 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 O1 H1A N1 0.82 1.88 2.609(13) 147.4 . O4 H4 N2 0.82 1.86 2.582(12) 146.5 . O5 H5 N3 0.82 1.87 2.613(10) 149.2 . O8 H8 N4 0.82 1.84 2.574(11) 148.8 . O9 H9A N6 0.82 1.84 2.572(12) 148.0 . O12 H12A N5 0.82 1.81 2.547(12) 148.3 . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.987 _refine_diff_density_min -0.553 _refine_diff_density_rms 0.137 #============================================================================== data_murugan3 _database_code_depnum_ccdc_archive 'CCDC 296813' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C40 H40 N4 O4' _chemical_formula_sum 'C40 H40 N4 O4' _chemical_formula_weight 640.76 _chemical_absolute_configuration syn loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 10.0407(13) _cell_length_b 15.0369(16) _cell_length_c 22.816(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3444.7(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 20 _cell_measurement_theta_max 30 _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.236 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1360 _exptl_absorpt_coefficient_mu 0.642 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_factor_muR 0.000 _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 3 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied. ; _exptl_absorpt_correction_T_min 0.8379 _exptl_absorpt_correction_T_max 0.9899 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'cad4 diffractometer' _diffrn_measurement_method 'omega twotheta' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count ? _diffrn_standards_interval_time '1 hour' _diffrn_standards_decay_% 0 _diffrn_reflns_number 3516 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0195 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.52 _diffrn_reflns_theta_max 67.96 _reflns_number_total 3516 _reflns_number_gt 3051 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'cad4 system software' _computing_cell_refinement 'cad4 system software' _computing_data_reduction 'XCAD4 (WINGX)' _computing_structure_solution 'SIR92 (WINGX)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP32 (WINGX)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0620P)^2^+0.3677P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0067(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.4(3) _refine_ls_number_reflns 3516 _refine_ls_number_parameters 450 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0433 _refine_ls_R_factor_gt 0.0349 _refine_ls_wR_factor_ref 0.1005 _refine_ls_wR_factor_gt 0.0945 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 0.5735(2) 0.63598(16) -0.41751(9) 0.0432(5) Uani 1 1 d . . . H1 H 0.4993 0.5958 -0.4265 0.052 Uiso 1 1 calc R . . C2 C 0.6788(3) 0.62752(18) -0.46518(10) 0.0524(6) Uani 1 1 d . . . H2A H 0.7551 0.6638 -0.4549 0.063 Uiso 1 1 calc R . . H2B H 0.7083 0.5662 -0.4674 0.063 Uiso 1 1 calc R . . C3 C 0.6269(3) 0.6562(2) -0.52465(11) 0.0607(7) Uani 1 1 d . . . H3A H 0.5549 0.6171 -0.5365 0.073 Uiso 1 1 calc R . . H3B H 0.6975 0.6515 -0.5535 0.073 Uiso 1 1 calc R . . C4 C 0.5768(3) 0.7514(2) -0.52238(11) 0.0598(7) Uani 1 1 d . . . H4A H 0.5383 0.7671 -0.5600 0.072 Uiso 1 1 calc R . . H4B H 0.6511 0.7911 -0.5150 0.072 Uiso 1 1 calc R . . C5 C 0.4727(3) 0.7631(2) -0.47446(10) 0.0533(6) Uani 1 1 d . . . H5A H 0.3936 0.7297 -0.4849 0.064 Uiso 1 1 calc R . . H5B H 0.4481 0.8254 -0.4722 0.064 Uiso 1 1 calc R . . C6 C 0.5207(2) 0.73263(16) -0.41443(9) 0.0431(5) Uani 1 1 d . . . H6 H 0.5913 0.7723 -0.4004 0.052 Uiso 1 1 calc R . . C7 C 0.4247(2) 0.76510(17) -0.32260(11) 0.0465(5) Uani 1 1 d D . . C8 C 0.3266(2) 0.75244(16) -0.27625(10) 0.0443(5) Uani 1 1 d . . . C9 C 0.3534(2) 0.78106(16) -0.21957(10) 0.0467(5) Uani 1 1 d . . . H9 H 0.4305 0.8138 -0.2129 0.056 Uiso 1 1 calc R . . C10 C 0.2704(2) 0.76303(16) -0.17235(10) 0.0456(5) Uani 1 1 d . . . C11 C 0.1570(3) 0.71251(19) -0.18448(11) 0.0530(6) Uani 1 1 d . . . H11 H 0.0998 0.6980 -0.1539 0.064 Uiso 1 1 calc R . . C12 C 0.1269(3) 0.68350(19) -0.24006(11) 0.0570(7) Uani 1 1 d . . . H12 H 0.0500 0.6504 -0.2464 0.068 Uiso 1 1 calc R . . C13 C 0.2100(2) 0.70306(17) -0.28661(10) 0.0481(6) Uani 1 1 d . . . C14 C 0.3040(2) 0.79370(15) -0.11237(10) 0.0456(5) Uani 1 1 d . . . C15 C 0.3838(3) 0.86864(16) -0.10363(11) 0.0538(6) Uani 1 1 d . . . H15 H 0.4106 0.9015 -0.1361 0.065 Uiso 1 1 calc R . . C16 C 0.4242(3) 0.89571(17) -0.04866(11) 0.0550(6) Uani 1 1 d . . . H16 H 0.4787 0.9453 -0.0447 0.066 Uiso 1 1 calc R . . C17 C 0.3839(3) 0.84930(15) 0.00052(10) 0.0491(6) Uani 1 1 d . . . C18 C 0.3002(2) 0.77568(15) -0.00619(10) 0.0464(5) Uani 1 1 d . . . C19 C 0.2629(2) 0.74879(17) -0.06256(10) 0.0470(5) Uani 1 1 d . . . H19 H 0.2086 0.6991 -0.0667 0.056 Uiso 1 1 calc R . . C20 C 0.2604(3) 0.72247(18) 0.04474(11) 0.0496(6) Uani 1 1 d D . . C21 C 0.2793(3) 0.67818(16) 0.14388(10) 0.0472(5) Uani 1 1 d . . . H21 H 0.1933 0.6492 0.1371 0.057 Uiso 1 1 calc R . . C22 C 0.2730(3) 0.73058(18) 0.20083(10) 0.0547(6) Uani 1 1 d . . . H22A H 0.1956 0.7692 0.2000 0.066 Uiso 1 1 calc R . . H22B H 0.3515 0.7678 0.2039 0.066 Uiso 1 1 calc R . . C23 C 0.2649(3) 0.6705(2) 0.25450(11) 0.0622(7) Uani 1 1 d . . . H23A H 0.2687 0.7065 0.2897 0.075 Uiso 1 1 calc R . . H23B H 0.1805 0.6391 0.2544 0.075 Uiso 1 1 calc R . . C24 C 0.3779(3) 0.6038(2) 0.25509(11) 0.0644(8) Uani 1 1 d . . . H24A H 0.3691 0.5652 0.2889 0.077 Uiso 1 1 calc R . . H24B H 0.4622 0.6349 0.2581 0.077 Uiso 1 1 calc R . . C25 C 0.3760(3) 0.54843(19) 0.19953(10) 0.0595(7) Uani 1 1 d . . . H25A H 0.2931 0.5155 0.1974 0.071 Uiso 1 1 calc R . . H25B H 0.4486 0.5059 0.2006 0.071 Uiso 1 1 calc R . . C26 C 0.3898(3) 0.60683(17) 0.14541(10) 0.0495(6) Uani 1 1 d . . . H26 H 0.4773 0.6357 0.1455 0.059 Uiso 1 1 calc R . . C27 C 0.4561(3) 0.56134(17) 0.05004(11) 0.0502(6) Uani 1 1 d D . . C28 C 0.4267(2) 0.52285(15) -0.00693(10) 0.0460(5) Uani 1 1 d . . . C29 C 0.3035(3) 0.48007(17) -0.01646(11) 0.0526(6) Uani 1 1 d . . . C30 C 0.2703(3) 0.4530(2) -0.07269(12) 0.0624(7) Uani 1 1 d . . . H30 H 0.1886 0.4257 -0.0796 0.075 Uiso 1 1 calc R . . C31 C 0.3571(3) 0.46613(18) -0.11806(11) 0.0563(6) Uani 1 1 d . . . H31 H 0.3328 0.4475 -0.1554 0.068 Uiso 1 1 calc R . . C32 C 0.4816(2) 0.50682(15) -0.11013(10) 0.0464(5) Uani 1 1 d . . . C33 C 0.5132(2) 0.53472(15) -0.05422(10) 0.0461(5) Uani 1 1 d . . . H33 H 0.5947 0.5623 -0.0478 0.055 Uiso 1 1 calc R . . C34 C 0.5733(2) 0.51984(16) -0.16053(10) 0.0449(5) Uani 1 1 d . . . C35 C 0.7115(3) 0.51233(18) -0.15373(11) 0.0545(6) Uani 1 1 d . . . H35 H 0.7460 0.4966 -0.1173 0.065 Uiso 1 1 calc R . . C36 C 0.7972(3) 0.5275(2) -0.19934(12) 0.0603(7) Uani 1 1 d . . . H36 H 0.8884 0.5215 -0.1935 0.072 Uiso 1 1 calc R . . C37 C 0.7499(2) 0.55177(18) -0.25417(11) 0.0505(6) Uani 1 1 d . . . C38 C 0.6109(2) 0.55651(15) -0.26308(10) 0.0427(5) Uani 1 1 d . . . C39 C 0.5266(2) 0.54040(15) -0.21601(10) 0.0460(5) Uani 1 1 d . . . H39 H 0.4351 0.5435 -0.2220 0.055 Uiso 1 1 calc R . . C40 C 0.5582(2) 0.58065(17) -0.32070(11) 0.0448(5) Uani 1 1 d D . . N1 N 0.40938(18) 0.73374(13) -0.37361(8) 0.0439(4) Uani 1 1 d . . . N2 N 0.3072(2) 0.73892(14) 0.09536(8) 0.0503(5) Uani 1 1 d . . . N3 N 0.3752(2) 0.55381(14) 0.09258(8) 0.0517(5) Uani 1 1 d . . . N4 N 0.63189(19) 0.61069(13) -0.36144(8) 0.0462(5) Uani 1 1 d . . . O1 O 0.17853(19) 0.67224(15) -0.34034(7) 0.0646(5) Uani 1 1 d . . . H1' H 0.2307 0.6926 -0.3645 0.097 Uiso 1 1 calc R . . O2 O 0.4277(2) 0.87653(13) 0.05361(7) 0.0667(5) Uani 1 1 d . . . H2' H 0.4031 0.8412 0.0788 0.100 Uiso 1 1 calc R . . O3 O 0.2167(2) 0.46611(14) 0.02761(8) 0.0677(5) Uani 1 1 d . . . H3' H 0.2488 0.4841 0.0584 0.102 Uiso 1 1 calc R . . O4 O 0.83677(18) 0.57180(16) -0.29685(8) 0.0716(6) Uani 1 1 d . . . H4' H 0.7960 0.5863 -0.3265 0.107 Uiso 1 1 calc R . . H7 H 0.5003(18) 0.7933(17) -0.3104(11) 0.062(8) Uiso 1 1 d D . . H20 H 0.206(2) 0.6767(12) 0.0358(10) 0.047(7) Uiso 1 1 d D . . H27 H 0.5365(16) 0.5893(17) 0.0531(11) 0.055(8) Uiso 1 1 d D . . H40 H 0.4689(12) 0.5738(19) -0.3266(11) 0.061(8) Uiso 1 1 d 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 0.0352(11) 0.0487(12) 0.0457(11) 0.0007(10) 0.0032(10) -0.0064(10) C2 0.0405(12) 0.0577(14) 0.0591(14) -0.0004(12) 0.0109(11) -0.0024(12) C3 0.0489(14) 0.0847(19) 0.0486(13) -0.0066(13) 0.0091(12) -0.0090(15) C4 0.0516(15) 0.0805(18) 0.0472(13) 0.0090(13) 0.0052(12) 0.0002(15) C5 0.0424(13) 0.0672(16) 0.0501(13) 0.0077(12) 0.0020(11) 0.0014(13) C6 0.0329(11) 0.0515(13) 0.0449(12) 0.0019(10) 0.0044(9) -0.0042(10) C7 0.0385(12) 0.0516(13) 0.0493(13) 0.0026(11) 0.0006(10) -0.0034(11) C8 0.0382(11) 0.0464(11) 0.0483(12) 0.0037(10) 0.0021(10) 0.0010(10) C9 0.0396(12) 0.0497(12) 0.0508(13) 0.0008(11) 0.0030(10) -0.0010(11) C10 0.0425(12) 0.0479(13) 0.0463(12) 0.0043(10) 0.0048(10) 0.0046(11) C11 0.0432(13) 0.0646(15) 0.0511(13) 0.0043(12) 0.0097(11) -0.0032(12) C12 0.0399(13) 0.0748(17) 0.0562(14) 0.0019(13) 0.0047(12) -0.0100(13) C13 0.0398(12) 0.0598(14) 0.0448(12) 0.0044(11) 0.0005(11) 0.0006(12) C14 0.0448(13) 0.0439(12) 0.0481(12) 0.0018(10) 0.0045(11) 0.0033(11) C15 0.0643(16) 0.0456(12) 0.0516(13) 0.0054(11) 0.0103(13) -0.0037(12) C16 0.0604(15) 0.0454(13) 0.0593(14) -0.0014(11) 0.0072(13) -0.0081(12) C17 0.0524(14) 0.0441(12) 0.0509(13) -0.0029(10) 0.0054(12) 0.0019(11) C18 0.0442(13) 0.0464(12) 0.0487(12) 0.0033(10) 0.0036(11) 0.0019(11) C19 0.0443(13) 0.0481(12) 0.0486(13) 0.0021(10) 0.0032(10) -0.0027(11) C20 0.0490(14) 0.0515(14) 0.0483(13) 0.0023(11) 0.0020(11) -0.0031(12) C21 0.0458(13) 0.0488(12) 0.0469(12) 0.0043(10) 0.0031(11) -0.0038(11) C22 0.0544(15) 0.0589(15) 0.0508(13) -0.0008(12) 0.0085(12) 0.0031(13) C23 0.0640(17) 0.0759(17) 0.0467(13) 0.0035(13) 0.0126(13) 0.0118(15) C24 0.0583(16) 0.087(2) 0.0477(13) 0.0101(14) 0.0076(13) 0.0131(16) C25 0.0571(15) 0.0650(16) 0.0563(14) 0.0122(13) 0.0113(13) 0.0156(14) C26 0.0445(12) 0.0585(14) 0.0456(12) 0.0009(11) 0.0062(11) 0.0002(12) C27 0.0462(14) 0.0509(14) 0.0535(13) 0.0013(11) 0.0046(12) -0.0019(11) C28 0.0434(12) 0.0446(12) 0.0500(12) 0.0017(10) 0.0033(11) 0.0007(11) C29 0.0494(14) 0.0498(13) 0.0587(14) -0.0002(11) 0.0145(12) -0.0087(12) C30 0.0500(15) 0.0693(17) 0.0679(16) -0.0078(14) 0.0051(13) -0.0197(14) C31 0.0546(15) 0.0620(15) 0.0522(13) -0.0068(12) 0.0027(12) -0.0133(14) C32 0.0454(13) 0.0425(11) 0.0512(13) 0.0010(10) 0.0058(11) -0.0010(11) C33 0.0408(12) 0.0456(12) 0.0520(13) -0.0004(10) 0.0051(11) -0.0039(11) C34 0.0420(12) 0.0428(11) 0.0499(12) -0.0014(10) 0.0040(11) 0.0018(11) C35 0.0493(14) 0.0603(15) 0.0538(14) 0.0091(12) -0.0018(12) 0.0069(13) C36 0.0384(13) 0.0769(18) 0.0657(16) 0.0117(14) 0.0020(12) 0.0121(13) C37 0.0385(12) 0.0554(14) 0.0577(14) 0.0057(12) 0.0076(11) 0.0049(11) C38 0.0375(11) 0.0407(11) 0.0498(12) -0.0006(10) 0.0031(10) 0.0007(10) C39 0.0386(12) 0.0456(12) 0.0540(13) -0.0005(10) 0.0043(11) -0.0006(10) C40 0.0358(12) 0.0454(12) 0.0532(13) 0.0007(10) 0.0018(10) -0.0033(10) N1 0.0347(9) 0.0532(11) 0.0438(10) 0.0029(8) 0.0034(8) -0.0012(9) N2 0.0531(12) 0.0508(11) 0.0470(11) 0.0034(9) 0.0025(10) -0.0021(10) N3 0.0546(12) 0.0509(11) 0.0495(11) 0.0024(9) 0.0087(10) 0.0012(10) N4 0.0385(10) 0.0494(10) 0.0506(10) 0.0041(9) 0.0026(9) -0.0005(9) O1 0.0507(10) 0.0958(14) 0.0471(9) -0.0012(9) -0.0005(8) -0.0216(11) O2 0.0819(14) 0.0654(11) 0.0529(10) -0.0032(9) -0.0006(10) -0.0201(11) O3 0.0588(11) 0.0790(13) 0.0654(11) -0.0051(10) 0.0218(10) -0.0213(11) O4 0.0392(9) 0.1111(17) 0.0647(11) 0.0224(12) 0.0084(9) 0.0078(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 N4 1.458(3) . ? C1 C2 1.522(3) . ? C1 C6 1.548(3) . ? C1 H1 0.9800 . ? C2 C3 1.516(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.517(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.523(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.523(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 N1 1.455(3) . ? C6 H6 0.9800 . ? C7 N1 1.265(3) . ? C7 C8 1.457(3) . ? C7 H7 0.913(10) . ? C8 C9 1.389(3) . ? C8 C13 1.407(3) . ? C9 C10 1.389(3) . ? C9 H9 0.9300 . ? C10 C11 1.397(4) . ? C10 C14 1.483(3) . ? C11 C12 1.375(4) . ? C11 H11 0.9300 . ? C12 C13 1.382(3) . ? C12 H12 0.9300 . ? C13 O1 1.348(3) . ? C14 C19 1.385(3) . ? C14 C15 1.397(3) . ? C15 C16 1.380(3) . ? C15 H15 0.9300 . ? C16 C17 1.382(3) . ? C16 H16 0.9300 . ? C17 O2 1.352(3) . ? C17 C18 1.399(3) . ? C18 C19 1.399(3) . ? C18 C20 1.466(3) . ? C19 H19 0.9300 . ? C20 N2 1.271(3) . ? C20 H20 0.905(10) . ? C21 N2 1.462(3) . ? C21 C22 1.521(3) . ? C21 C26 1.544(3) . ? C21 H21 0.9800 . ? C22 C23 1.524(3) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.514(4) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 C25 1.517(4) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 C26 1.521(3) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 N3 1.453(3) . ? C26 H26 0.9800 . ? C27 N3 1.271(3) . ? C27 C28 1.453(3) . ? C27 H27 0.912(10) . ? C28 C33 1.396(3) . ? C28 C29 1.411(4) . ? C29 O3 1.347(3) . ? C29 C30 1.387(4) . ? C30 C31 1.368(4) . ? C30 H30 0.9300 . ? C31 C32 1.403(4) . ? C31 H31 0.9300 . ? C32 C33 1.380(3) . ? C32 C34 1.486(3) . ? C33 H33 0.9300 . ? C34 C39 1.385(3) . ? C34 C35 1.402(3) . ? C35 C36 1.369(3) . ? C35 H35 0.9300 . ? C36 C37 1.387(3) . ? C36 H36 0.9300 . ? C37 O4 1.341(3) . ? C37 C38 1.413(3) . ? C38 C39 1.389(3) . ? C38 C40 1.463(3) . ? C39 H39 0.9300 . ? C40 N4 1.271(3) . ? C40 H40 0.913(10) . ? O1 H1' 0.8200 . ? O2 H2' 0.8200 . ? O3 H3' 0.8200 . ? O4 H4' 0.8200 . ? 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 N4 C1 C2 108.99(19) . . ? N4 C1 C6 110.03(18) . . ? C2 C1 C6 110.40(19) . . ? N4 C1 H1 109.1 . . ? C2 C1 H1 109.1 . . ? C6 C1 H1 109.1 . . ? C3 C2 C1 112.1(2) . . ? C3 C2 H2A 109.2 . . ? C1 C2 H2A 109.2 . . ? C3 C2 H2B 109.2 . . ? C1 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? C2 C3 C4 110.6(2) . . ? C2 C3 H3A 109.5 . . ? C4 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? C4 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? C3 C4 C5 111.2(2) . . ? C3 C4 H4A 109.4 . . ? C5 C4 H4A 109.4 . . ? C3 C4 H4B 109.4 . . ? C5 C4 H4B 109.4 . . ? H4A C4 H4B 108.0 . . ? C4 C5 C6 113.2(2) . . ? C4 C5 H5A 108.9 . . ? C6 C5 H5A 108.9 . . ? C4 C5 H5B 108.9 . . ? C6 C5 H5B 108.9 . . ? H5A C5 H5B 107.8 . . ? N1 C6 C5 109.20(18) . . ? N1 C6 C1 107.61(18) . . ? C5 C6 C1 110.5(2) . . ? N1 C6 H6 109.8 . . ? C5 C6 H6 109.8 . . ? C1 C6 H6 109.8 . . ? N1 C7 C8 122.5(2) . . ? N1 C7 H7 123.7(17) . . ? C8 C7 H7 113.7(17) . . ? C9 C8 C13 118.8(2) . . ? C9 C8 C7 120.3(2) . . ? C13 C8 C7 120.6(2) . . ? C8 C9 C10 123.1(2) . . ? C8 C9 H9 118.5 . . ? C10 C9 H9 118.5 . . ? C9 C10 C11 116.2(2) . . ? C9 C10 C14 121.2(2) . . ? C11 C10 C14 122.5(2) . . ? C12 C11 C10 122.3(2) . . ? C12 C11 H11 118.9 . . ? C10 C11 H11 118.9 . . ? C11 C12 C13 120.6(2) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? O1 C13 C12 119.0(2) . . ? O1 C13 C8 122.0(2) . . ? C12 C13 C8 119.0(2) . . ? C19 C14 C15 116.6(2) . . ? C19 C14 C10 122.5(2) . . ? C15 C14 C10 120.9(2) . . ? C16 C15 C14 122.4(2) . . ? C16 C15 H15 118.8 . . ? C14 C15 H15 118.8 . . ? C15 C16 C17 120.2(2) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? O2 C17 C16 118.6(2) . . ? O2 C17 C18 122.2(2) . . ? C16 C17 C18 119.1(2) . . ? C17 C18 C19 119.3(2) . . ? C17 C18 C20 120.6(2) . . ? C19 C18 C20 119.9(2) . . ? C14 C19 C18 122.3(2) . . ? C14 C19 H19 118.9 . . ? C18 C19 H19 118.9 . . ? N2 C20 C18 120.9(2) . . ? N2 C20 H20 125.2(15) . . ? C18 C20 H20 113.8(15) . . ? N2 C21 C22 109.3(2) . . ? N2 C21 C26 108.28(19) . . ? C22 C21 C26 111.8(2) . . ? N2 C21 H21 109.1 . . ? C22 C21 H21 109.1 . . ? C26 C21 H21 109.1 . . ? C21 C22 C23 112.4(2) . . ? C21 C22 H22A 109.1 . . ? C23 C22 H22A 109.1 . . ? C21 C22 H22B 109.1 . . ? C23 C22 H22B 109.1 . . ? H22A C22 H22B 107.9 . . ? C24 C23 C22 111.1(2) . . ? C24 C23 H23A 109.4 . . ? C22 C23 H23A 109.4 . . ? C24 C23 H23B 109.4 . . ? C22 C23 H23B 109.4 . . ? H23A C23 H23B 108.0 . . ? C23 C24 C25 110.3(2) . . ? C23 C24 H24A 109.6 . . ? C25 C24 H24A 109.6 . . ? C23 C24 H24B 109.6 . . ? C25 C24 H24B 109.6 . . ? H24A C24 H24B 108.1 . . ? C24 C25 C26 111.1(2) . . ? C24 C25 H25A 109.4 . . ? C26 C25 H25A 109.4 . . ? C24 C25 H25B 109.4 . . ? C26 C25 H25B 109.4 . . ? H25A C25 H25B 108.0 . . ? N3 C26 C25 110.3(2) . . ? N3 C26 C21 106.9(2) . . ? C25 C26 C21 110.7(2) . . ? N3 C26 H26 109.6 . . ? C25 C26 H26 109.6 . . ? C21 C26 H26 109.6 . . ? N3 C27 C28 121.2(2) . . ? N3 C27 H27 123.2(17) . . ? C28 C27 H27 115.6(17) . . ? C33 C28 C29 119.0(2) . . ? C33 C28 C27 120.9(2) . . ? C29 C28 C27 119.8(2) . . ? O3 C29 C30 119.3(2) . . ? O3 C29 C28 121.6(2) . . ? C30 C29 C28 119.2(2) . . ? C31 C30 C29 120.3(2) . . ? C31 C30 H30 119.9 . . ? C29 C30 H30 119.9 . . ? C30 C31 C32 122.2(2) . . ? C30 C31 H31 118.9 . . ? C32 C31 H31 118.9 . . ? C33 C32 C31 117.2(2) . . ? C33 C32 C34 122.2(2) . . ? C31 C32 C34 120.6(2) . . ? C32 C33 C28 122.2(2) . . ? C32 C33 H33 118.9 . . ? C28 C33 H33 118.9 . . ? C39 C34 C35 117.0(2) . . ? C39 C34 C32 121.8(2) . . ? C35 C34 C32 121.2(2) . . ? C36 C35 C34 121.6(2) . . ? C36 C35 H35 119.2 . . ? C34 C35 H35 119.2 . . ? C35 C36 C37 120.9(2) . . ? C35 C36 H36 119.5 . . ? C37 C36 H36 119.5 . . ? O4 C37 C36 119.4(2) . . ? O4 C37 C38 121.8(2) . . ? C36 C37 C38 118.8(2) . . ? C39 C38 C37 118.8(2) . . ? C39 C38 C40 121.2(2) . . ? C37 C38 C40 119.9(2) . . ? C34 C39 C38 122.7(2) . . ? C34 C39 H39 118.7 . . ? C38 C39 H39 118.7 . . ? N4 C40 C38 122.3(2) . . ? N4 C40 H40 120.2(18) . . ? C38 C40 H40 117.4(17) . . ? C7 N1 C6 120.0(2) . . ? C20 N2 C21 119.7(2) . . ? C27 N3 C26 121.3(2) . . ? C40 N4 C1 120.0(2) . . ? C13 O1 H1' 109.5 . . ? C17 O2 H2' 109.5 . . ? C29 O3 H3' 109.5 . . ? C37 O4 H4' 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N4 C1 C2 C3 -177.8(2) . . . . ? C6 C1 C2 C3 -56.8(3) . . . . ? C1 C2 C3 C4 57.5(3) . . . . ? C2 C3 C4 C5 -55.0(3) . . . . ? C3 C4 C5 C6 54.3(3) . . . . ? C4 C5 C6 N1 -171.5(2) . . . . ? C4 C5 C6 C1 -53.4(3) . . . . ? N4 C1 C6 N1 -66.8(2) . . . . ? C2 C1 C6 N1 172.88(18) . . . . ? N4 C1 C6 C5 174.08(18) . . . . ? C2 C1 C6 C5 53.7(2) . . . . ? N1 C7 C8 C9 174.1(2) . . . . ? N1 C7 C8 C13 0.8(4) . . . . ? C13 C8 C9 C10 0.2(4) . . . . ? C7 C8 C9 C10 -173.2(2) . . . . ? C8 C9 C10 C11 0.9(4) . . . . ? C8 C9 C10 C14 179.0(2) . . . . ? C9 C10 C11 C12 -1.3(4) . . . . ? C14 C10 C11 C12 -179.4(3) . . . . ? C10 C11 C12 C13 0.5(4) . . . . ? C11 C12 C13 O1 178.9(3) . . . . ? C11 C12 C13 C8 0.6(4) . . . . ? C9 C8 C13 O1 -179.2(2) . . . . ? C7 C8 C13 O1 -5.8(4) . . . . ? C9 C8 C13 C12 -1.0(4) . . . . ? C7 C8 C13 C12 172.5(2) . . . . ? C9 C10 C14 C19 -151.2(2) . . . . ? C11 C10 C14 C19 26.8(4) . . . . ? C9 C10 C14 C15 26.5(4) . . . . ? C11 C10 C14 C15 -155.5(2) . . . . ? C19 C14 C15 C16 2.2(4) . . . . ? C10 C14 C15 C16 -175.7(3) . . . . ? C14 C15 C16 C17 -1.2(4) . . . . ? C15 C16 C17 O2 178.6(3) . . . . ? C15 C16 C17 C18 -1.0(4) . . . . ? O2 C17 C18 C19 -177.4(2) . . . . ? C16 C17 C18 C19 2.2(4) . . . . ? O2 C17 C18 C20 -2.4(4) . . . . ? C16 C17 C18 C20 177.2(2) . . . . ? C15 C14 C19 C18 -0.9(4) . . . . ? C10 C14 C19 C18 176.9(2) . . . . ? C17 C18 C19 C14 -1.3(4) . . . . ? C20 C18 C19 C14 -176.3(2) . . . . ? C17 C18 C20 N2 -4.1(4) . . . . ? C19 C18 C20 N2 170.8(2) . . . . ? N2 C21 C22 C23 -171.5(2) . . . . ? C26 C21 C22 C23 -51.6(3) . . . . ? C21 C22 C23 C24 54.2(3) . . . . ? C22 C23 C24 C25 -57.5(3) . . . . ? C23 C24 C25 C26 59.3(3) . . . . ? C24 C25 C26 N3 -174.6(2) . . . . ? C24 C25 C26 C21 -56.5(3) . . . . ? N2 C21 C26 N3 -66.9(2) . . . . ? C22 C21 C26 N3 172.6(2) . . . . ? N2 C21 C26 C25 172.9(2) . . . . ? C22 C21 C26 C25 52.4(3) . . . . ? N3 C27 C28 C33 177.1(2) . . . . ? N3 C27 C28 C29 3.2(4) . . . . ? C33 C28 C29 O3 179.4(2) . . . . ? C27 C28 C29 O3 -6.6(4) . . . . ? C33 C28 C29 C30 -1.5(4) . . . . ? C27 C28 C29 C30 172.5(3) . . . . ? O3 C29 C30 C31 -179.7(3) . . . . ? C28 C29 C30 C31 1.2(4) . . . . ? C29 C30 C31 C32 0.0(5) . . . . ? C30 C31 C32 C33 -0.9(4) . . . . ? C30 C31 C32 C34 179.9(3) . . . . ? C31 C32 C33 C28 0.5(4) . . . . ? C34 C32 C33 C28 179.7(2) . . . . ? C29 C28 C33 C32 0.7(4) . . . . ? C27 C28 C33 C32 -173.3(2) . . . . ? C33 C32 C34 C39 -143.0(2) . . . . ? C31 C32 C34 C39 36.1(3) . . . . ? C33 C32 C34 C35 36.6(4) . . . . ? C31 C32 C34 C35 -144.3(3) . . . . ? C39 C34 C35 C36 2.1(4) . . . . ? C32 C34 C35 C36 -177.5(2) . . . . ? C34 C35 C36 C37 0.5(5) . . . . ? C35 C36 C37 O4 175.7(3) . . . . ? C35 C36 C37 C38 -3.0(4) . . . . ? O4 C37 C38 C39 -175.9(2) . . . . ? C36 C37 C38 C39 2.7(4) . . . . ? O4 C37 C38 C40 2.3(4) . . . . ? C36 C37 C38 C40 -179.1(2) . . . . ? C35 C34 C39 C38 -2.4(4) . . . . ? C32 C34 C39 C38 177.2(2) . . . . ? C37 C38 C39 C34 0.0(4) . . . . ? C40 C38 C39 C34 -178.2(2) . . . . ? C39 C38 C40 N4 167.4(2) . . . . ? C37 C38 C40 N4 -10.8(4) . . . . ? C8 C7 N1 C6 -167.6(2) . . . . ? C5 C6 N1 C7 -136.1(2) . . . . ? C1 C6 N1 C7 104.0(2) . . . . ? C18 C20 N2 C21 -172.3(2) . . . . ? C22 C21 N2 C20 -148.3(2) . . . . ? C26 C21 N2 C20 89.7(3) . . . . ? C28 C27 N3 C26 -167.0(2) . . . . ? C25 C26 N3 C27 -133.2(3) . . . . ? C21 C26 N3 C27 106.3(3) . . . . ? C38 C40 N4 C1 -178.3(2) . . . . ? C2 C1 N4 C40 -153.8(2) . . . . ? C6 C1 N4 C40 85.1(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 O1 H1' N1 0.82 1.91 2.609(3) 142.6 . O2 H2' N2 0.82 1.85 2.579(3) 146.8 . O3 H3' N3 0.82 1.82 2.544(3) 146.3 . O4 H4' N4 0.82 1.87 2.597(3) 147.7 . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 67.96 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.177 _refine_diff_density_min -0.118 _refine_diff_density_rms 0.033