# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Claudia Caltagirone' _publ_contact_author_email CCALTAGIRONE@UNICA.IT _publ_section_title ; Metal-induced pre-organization for anion recognition in a neutral cis-platin analogue ; loop_ _publ_author_name 'Claudia Caltagirone' 'Philip A. Gale' 'Francesco Isaia' 'Mark Light' 'Vito Lippolis' 'Andrea Mulas' #===END data_2009sot0307 _database_code_depnum_ccdc_archive 'CCDC 736406' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C16 H36 N), C28 H20 N6 O2, 2(C2 H3 O2) ' _chemical_formula_sum 'C64 H98 N8 O6' _chemical_formula_weight 1075.50 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.8189(4) _cell_length_b 22.0743(14) _cell_length_c 16.2914(11) _cell_angle_alpha 90.00 _cell_angle_beta 92.895(3) _cell_angle_gamma 90.00 _cell_volume 3167.4(3) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 18442 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 25.68 _exptl_crystal_description Rod _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.128 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1172 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9742 _exptl_absorpt_correction_T_max 0.9978 _exptl_absorpt_process_details ; SADABS V2.10 (Sheldrick, G.M., 2003) ; _exptl_special_details ; SADABS was used to perform the Absorption correction Parameter refinement on 10728 reflections reduced R(int) from 0.1867 to 0.0986 Ratio of minimum to maximum apparent transmission: 0.712829 The given Tmin and Tmax were generated using the SHELX SIZE command ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating Anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22442 _diffrn_reflns_av_R_equivalents 0.2297 _diffrn_reflns_av_sigmaI/netI 0.2015 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 25.03 _reflns_number_total 5583 _reflns_number_gt 2504 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'CAMERON (Watkin, et al., 1993)' _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The TBA in the acetate structure exhibited disorder. This was modelled as 2 different conformations of one arm and it was necessary to apply various constraints and restraints to the geometry and atomic displacement parameters in the model. These included: equal atomic displacement parameter constraints to each pair of disordered atoms, similarity restraints (0.01) to the atomic displacement parameters of bonded atoms. The geometries of each part of the disorder were restrained to be similar (0.01) to one of the better behaved arms. ; _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^)+(0.0868P)^2^+29.8813P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5583 _refine_ls_number_parameters 371 _refine_ls_number_restraints 25 _refine_ls_R_factor_all 0.3051 _refine_ls_R_factor_gt 0.1692 _refine_ls_wR_factor_ref 0.4070 _refine_ls_wR_factor_gt 0.3268 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.039 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.3022(3) 0.18675(11) 0.06249(15) 0.0452(8) Uani 1 1 d . . . N1 N 0.2470(3) 0.21716(14) 0.34964(18) 0.0384(9) Uani 1 1 d . . . H901 H 0.2850 0.1803 0.3513 0.046 Uiso 1 1 calc R . . N2 N 0.1941(3) 0.16313(12) 0.18230(18) 0.0371(9) Uani 1 1 d . . . H902 H 0.1746 0.1339 0.2170 0.044 Uiso 1 1 calc R . . N3 N 0.3709(3) -0.03716(13) 0.06530(19) 0.0432(9) Uani 1 1 d . . . C1 C 0.1784(4) 0.24530(16) 0.2817(2) 0.0368(10) Uani 1 1 d . . . C2 C 0.2449(4) 0.25727(19) 0.4140(2) 0.0487(12) Uani 1 1 d . . . H2 H 0.2828 0.2488 0.4684 0.058 Uiso 1 1 calc R . . C3 C 0.1809(4) 0.31098(18) 0.3891(3) 0.0513(12) Uani 1 1 d . . . H3 H 0.1693 0.3460 0.4221 0.062 Uiso 1 1 calc R . . C4 C 0.1352(4) 0.30469(15) 0.3052(2) 0.0380(10) Uani 1 1 d . . . C5 C 0.0650(4) 0.34155(18) 0.2465(3) 0.0494(12) Uani 1 1 d . . . H5 H 0.0370 0.3817 0.2604 0.059 Uiso 1 1 calc R . . C6 C 0.0354(5) 0.32062(18) 0.1680(3) 0.0560(13) Uani 1 1 d . . . H6 H -0.0152 0.3460 0.1283 0.067 Uiso 1 1 calc R . . C7 C 0.0794(4) 0.26215(17) 0.1462(2) 0.0416(11) Uani 1 1 d . . . H7 H 0.0585 0.2485 0.0915 0.050 Uiso 1 1 calc R . . C8 C 0.1512(4) 0.22447(16) 0.2014(2) 0.0383(10) Uani 1 1 d . . . C9 C 0.2640(4) 0.14940(16) 0.1121(2) 0.0347(10) Uani 1 1 d . . . C10 C 0.2965(4) 0.08269(15) 0.0990(2) 0.0314(10) Uani 1 1 d . . . C11 C 0.4072(4) 0.06843(15) 0.0446(2) 0.0326(10) Uani 1 1 d . . . H11 H 0.4595 0.0997 0.0177 0.039 Uiso 1 1 calc R . . C12 C 0.4411(4) 0.00808(16) 0.0298(2) 0.0324(10) Uani 1 1 d . . . C13 C 0.2628(5) -0.02283(18) 0.1176(3) 0.0517(13) Uani 1 1 d . . . H13 H 0.2120 -0.0550 0.1437 0.062 Uiso 1 1 calc R . . C14 C 0.2213(4) 0.03630(16) 0.1356(2) 0.0395(11) Uani 1 1 d . . . H14 H 0.1433 0.0443 0.1722 0.047 Uiso 1 1 calc R . . N4 N 0.7428(3) 0.18285(13) 0.36598(17) 0.0309(8) Uani 1 1 d . . . C15 C 0.7869(4) 0.18050(16) 0.2779(2) 0.0316(10) Uani 1 1 d . A . H15A H 0.8450 0.2177 0.2664 0.038 Uiso 1 1 calc R . . H15B H 0.8561 0.1456 0.2718 0.038 Uiso 1 1 calc R . . C16 C 0.6589(4) 0.17500(19) 0.2139(2) 0.0429(12) Uani 1 1 d . . . H16A H 0.5915 0.2107 0.2171 0.052 Uiso 1 1 calc R A . H16B H 0.5983 0.1384 0.2251 0.052 Uiso 1 1 calc R . . C17 C 0.7173(5) 0.1707(2) 0.1278(3) 0.0553(14) Uani 1 1 d . A . H17A H 0.7858 0.2053 0.1189 0.066 Uiso 1 1 calc R . . H17B H 0.6302 0.1739 0.0872 0.066 Uiso 1 1 calc R . . C18 C 0.8024(6) 0.1118(3) 0.1126(3) 0.0865(19) Uani 1 1 d . . . H18A H 0.8953 0.1105 0.1482 0.130 Uiso 1 1 calc R A . H18B H 0.8290 0.1100 0.0549 0.130 Uiso 1 1 calc R . . H18C H 0.7377 0.0773 0.1248 0.130 Uiso 1 1 calc R . . C19A C 0.6176(7) 0.13903(18) 0.3855(9) 0.0294(10) Uani 0.234(5) 1 d PDU A 1 H19A H 0.5346 0.1385 0.3422 0.035 Uiso 0.234(5) 1 calc PR A 1 H19B H 0.5756 0.1472 0.4396 0.035 Uiso 0.234(5) 1 calc PR A 1 C20A C 0.7117(6) 0.08186(14) 0.3858(5) 0.0389(12) Uani 0.234(5) 1 d PDU A 1 H20A H 0.8071 0.0884 0.4193 0.047 Uiso 0.234(5) 1 calc PR A 1 H20B H 0.7387 0.0723 0.3290 0.047 Uiso 0.234(5) 1 calc PR A 1 C21A C 0.6251(9) 0.02836(15) 0.4208(3) 0.117(2) Uani 0.234(5) 1 d PDU A 1 H21A H 0.6698 0.0176 0.4759 0.140 Uiso 0.234(5) 1 calc PR A 1 H21B H 0.5176 0.0397 0.4266 0.140 Uiso 0.234(5) 1 calc PR A 1 C22A C 0.635(2) -0.0252(2) 0.3636(4) 0.125(3) Uani 0.234(5) 1 d PDU A 1 H22A H 0.5613 -0.0200 0.3169 0.187 Uiso 0.234(5) 1 calc PR A 1 H22B H 0.6114 -0.0624 0.3932 0.187 Uiso 0.234(5) 1 calc PR A 1 H22C H 0.7373 -0.0278 0.3436 0.187 Uiso 0.234(5) 1 calc PR A 1 C19B C 0.6509(4) 0.12606(13) 0.3873(3) 0.0294(10) Uani 0.766(5) 1 d PDU A 2 H19C H 0.6288 0.1284 0.4462 0.035 Uiso 0.766(5) 1 calc PR A 2 H19D H 0.5524 0.1278 0.3555 0.035 Uiso 0.766(5) 1 calc PR A 2 C20B C 0.7213(4) 0.06498(12) 0.3723(3) 0.0389(12) Uani 0.766(5) 1 d PDU A 2 H20C H 0.8175 0.0612 0.4059 0.047 Uiso 0.766(5) 1 calc PR A 2 H20D H 0.7450 0.0615 0.3137 0.047 Uiso 0.766(5) 1 calc PR A 2 C21B C 0.6132(4) 0.01396(13) 0.3943(5) 0.117(2) Uani 0.766(5) 1 d PDU A 2 H21C H 0.5581 0.0256 0.4434 0.140 Uiso 0.766(5) 1 calc PR A 2 H21D H 0.5376 0.0073 0.3483 0.140 Uiso 0.766(5) 1 calc PR A 2 C22B C 0.7005(6) -0.04370(16) 0.4117(6) 0.125(3) Uani 0.766(5) 1 d PDU A 2 H22D H 0.7106 -0.0661 0.3603 0.187 Uiso 0.766(5) 1 calc PR A 2 H22E H 0.6461 -0.0686 0.4504 0.187 Uiso 0.766(5) 1 calc PR A 2 H22F H 0.8016 -0.0338 0.4358 0.187 Uiso 0.766(5) 1 calc PR A 2 C23 C 0.8890(4) 0.18269(17) 0.4193(2) 0.0305(10) Uani 1 1 d . A . H23A H 0.9407 0.2221 0.4126 0.037 Uiso 1 1 calc R . . H23B H 0.9563 0.1507 0.3991 0.037 Uiso 1 1 calc R . . C24 C 0.8691(4) 0.17210(17) 0.5116(2) 0.0414(11) Uani 1 1 d . . . H24A H 0.7967 0.2021 0.5320 0.050 Uiso 1 1 calc R A . H24B H 0.8266 0.1312 0.5199 0.050 Uiso 1 1 calc R . . C25 C 1.0194(5) 0.17783(19) 0.5594(2) 0.0476(13) Uani 1 1 d . A . H25A H 1.0930 0.1493 0.5367 0.057 Uiso 1 1 calc R . . H25B H 1.0592 0.2194 0.5529 0.057 Uiso 1 1 calc R . . C26 C 1.0051(6) 0.1648(2) 0.6491(3) 0.0708(18) Uani 1 1 d . . . H26A H 0.9314 0.1927 0.6716 0.106 Uiso 1 1 calc R A . H26B H 1.1041 0.1701 0.6783 0.106 Uiso 1 1 calc R . . H26C H 0.9705 0.1230 0.6559 0.106 Uiso 1 1 calc R . . C27 C 0.6498(4) 0.24008(12) 0.3824(2) 0.0389(11) Uani 1 1 d D A . H27A H 0.5513 0.2367 0.3508 0.047 Uiso 1 1 calc R . . H27B H 0.6280 0.2405 0.4414 0.047 Uiso 1 1 calc R . . C28 C 0.7198(3) 0.30020(11) 0.3617(2) 0.0403(11) Uani 1 1 d D . . H28A H 0.7464 0.3002 0.3034 0.048 Uiso 1 1 calc R A . H28B H 0.8145 0.3061 0.3961 0.048 Uiso 1 1 calc R . . C29 C 0.6102(4) 0.35262(11) 0.3765(2) 0.0463(12) Uani 1 1 d D A . H29A H 0.5128 0.3453 0.3452 0.056 Uiso 1 1 calc R . . H29B H 0.5893 0.3544 0.4356 0.056 Uiso 1 1 calc R . . C30 C 0.6760(5) 0.41233(13) 0.3503(3) 0.0617(15) Uani 1 1 d D . . H30A H 0.7755 0.4184 0.3787 0.093 Uiso 1 1 calc R A . H30B H 0.6078 0.4454 0.3644 0.093 Uiso 1 1 calc R . . H30C H 0.6875 0.4120 0.2908 0.093 Uiso 1 1 calc R . . O2 O 0.0871(3) 0.08550(12) 0.29869(17) 0.0475(8) Uani 1 1 d . . . O3 O 0.2909(3) 0.09657(14) 0.3821(2) 0.0807(12) Uani 1 1 d . . . C31 C 0.1801(4) 0.06736(19) 0.3549(3) 0.0618(15) Uani 1 1 d . . . C32 C 0.1541(7) 0.0025(2) 0.3831(5) 0.146(3) Uani 1 1 d . . . H32A H 0.2351 -0.0236 0.3640 0.219 Uiso 1 1 calc R . . H32B H 0.0558 -0.0119 0.3600 0.219 Uiso 1 1 calc R . . H32C H 0.1546 0.0013 0.4432 0.219 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0590(15) 0.0291(13) 0.0491(15) -0.0012(12) 0.0184(12) 0.0087(12) N1 0.0289(14) 0.0392(17) 0.0476(18) -0.0065(15) 0.0072(14) -0.0012(14) N2 0.0480(16) 0.0218(14) 0.0432(17) -0.0078(13) 0.0197(14) -0.0074(13) N3 0.0537(17) 0.0277(16) 0.0507(18) -0.0067(14) 0.0261(15) -0.0018(14) C1 0.0312(16) 0.0327(19) 0.048(2) -0.0061(17) 0.0193(15) -0.0039(16) C2 0.0379(19) 0.067(3) 0.042(2) -0.012(2) 0.0137(17) -0.017(2) C3 0.052(2) 0.033(2) 0.071(3) -0.015(2) 0.020(2) -0.0122(19) C4 0.0403(17) 0.0230(17) 0.053(2) -0.0157(16) 0.0246(16) -0.0050(16) C5 0.052(2) 0.035(2) 0.064(3) 0.0053(19) 0.0237(19) 0.0123(18) C6 0.068(2) 0.038(2) 0.063(3) 0.011(2) 0.018(2) 0.020(2) C7 0.050(2) 0.037(2) 0.039(2) 0.0055(17) 0.0136(17) 0.0094(18) C8 0.0386(17) 0.0269(18) 0.051(2) -0.0013(17) 0.0232(16) 0.0061(16) C9 0.0324(17) 0.0288(18) 0.044(2) 0.0013(16) 0.0079(16) 0.0056(16) C10 0.0285(16) 0.0242(18) 0.042(2) -0.0095(15) 0.0030(16) -0.0016(15) C11 0.0335(17) 0.0249(17) 0.0401(19) -0.0092(15) 0.0096(15) -0.0068(15) C12 0.0330(17) 0.0313(18) 0.0325(19) -0.0083(16) -0.0036(15) -0.0037(16) C13 0.062(2) 0.035(2) 0.061(2) -0.0076(19) 0.029(2) -0.0016(19) C14 0.0388(18) 0.0305(19) 0.050(2) -0.0152(17) 0.0112(17) -0.0026(17) N4 0.0279(13) 0.0319(15) 0.0328(15) -0.0007(13) 0.0022(12) -0.0029(13) C15 0.0246(16) 0.0353(19) 0.0351(19) 0.0035(16) 0.0031(15) -0.0034(16) C16 0.0373(19) 0.052(2) 0.039(2) 0.0065(19) -0.0091(18) -0.0023(19) C17 0.060(3) 0.061(3) 0.043(2) -0.006(2) -0.011(2) -0.001(2) C18 0.078(3) 0.130(4) 0.050(3) -0.028(3) -0.016(3) 0.037(3) C19A 0.0092(17) 0.0263(16) 0.052(2) 0.0096(18) -0.0006(17) 0.0073(15) C20A 0.042(2) 0.0206(16) 0.055(3) -0.0112(19) 0.0133(19) 0.0025(15) C21A 0.052(3) 0.0188(17) 0.284(6) 0.030(2) 0.048(3) 0.0025(19) C22A 0.078(4) 0.036(2) 0.263(8) 0.022(3) 0.038(5) 0.011(3) C19B 0.0092(17) 0.0263(16) 0.052(2) 0.0096(18) -0.0006(17) 0.0073(15) C20B 0.042(2) 0.0206(16) 0.055(3) -0.0112(19) 0.0133(19) 0.0025(15) C21B 0.052(3) 0.0188(17) 0.284(6) 0.030(2) 0.048(3) 0.0025(19) C22B 0.078(4) 0.036(2) 0.263(8) 0.022(3) 0.038(5) 0.011(3) C23 0.0232(15) 0.0382(19) 0.0299(18) 0.0059(16) 0.0009(14) 0.0010(16) C24 0.051(2) 0.029(2) 0.044(2) -0.0018(17) 0.0010(19) -0.0075(18) C25 0.061(2) 0.049(2) 0.033(2) -0.0005(19) -0.0059(19) 0.004(2) C26 0.104(4) 0.052(3) 0.055(3) -0.005(2) -0.008(3) 0.006(3) C27 0.0288(17) 0.041(2) 0.047(2) 0.0091(18) 0.0079(16) 0.0097(17) C28 0.0301(18) 0.054(2) 0.037(2) -0.0034(18) 0.0007(17) 0.0031(18) C29 0.046(2) 0.048(2) 0.044(2) 0.0001(19) 0.0057(19) 0.0142(19) C30 0.061(3) 0.035(2) 0.089(3) -0.008(2) 0.002(3) 0.006(2) O2 0.0418(14) 0.0421(15) 0.0591(17) 0.0039(13) 0.0092(13) 0.0029(12) O3 0.0370(15) 0.0546(18) 0.150(3) 0.035(2) -0.0004(19) 0.0089(15) C31 0.0275(18) 0.045(2) 0.114(4) 0.022(2) 0.017(2) 0.0039(19) C32 0.071(4) 0.070(3) 0.294(8) 0.105(4) -0.017(5) -0.008(3) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C9 1.214(4) . ? N1 C2 1.373(5) . ? N1 C1 1.381(5) . ? N2 C9 1.361(5) . ? N2 C8 1.444(4) . ? N3 C12 1.323(5) . ? N3 C13 1.348(5) . ? C1 C8 1.397(5) . ? C1 C4 1.423(5) . ? C2 C3 1.366(6) . ? C3 C4 1.413(6) . ? C4 C5 1.378(5) . ? C5 C6 1.372(6) . ? C6 C7 1.399(5) . ? C7 C8 1.357(5) . ? C9 C10 1.517(5) . ? C10 C14 1.372(5) . ? C10 C11 1.388(5) . ? C11 C12 1.389(5) . ? C12 C12 1.500(7) 3_655 ? C13 C14 1.391(5) . ? N4 C19A 1.514(7) . ? N4 C15 1.506(4) . ? N4 C23 1.518(4) . ? N4 C27 1.537(4) . ? N4 C19B 1.542(4) . ? C15 C16 1.503(5) . ? C16 C17 1.522(6) . ? C17 C18 1.527(7) . ? C19A C20A 1.511(5) . ? C20A C21A 1.532(6) . ? C21A C22A 1.510(6) . ? C19B C20B 1.510(4) . ? C20B C21B 1.530(5) . ? C21B C22B 1.507(5) . ? C23 C24 1.539(5) . ? C24 C25 1.508(6) . ? C25 C26 1.501(6) . ? C27 C28 1.509(4) . ? C28 C29 1.535(4) . ? C29 C30 1.511(4) . ? O2 C31 1.263(5) . ? O3 C31 1.234(5) . ? C31 C32 1.525(7) . ? 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 N1 C1 107.5(3) . . ? C9 N2 C8 121.6(3) . . ? C12 N3 C13 117.4(3) . . ? N1 C1 C8 130.6(3) . . ? N1 C1 C4 108.2(3) . . ? C8 C1 C4 121.3(3) . . ? C3 C2 N1 110.7(4) . . ? C2 C3 C4 107.2(3) . . ? C5 C4 C3 135.2(3) . . ? C5 C4 C1 118.4(3) . . ? C3 C4 C1 106.4(3) . . ? C6 C5 C4 120.3(4) . . ? C5 C6 C7 120.4(4) . . ? C8 C7 C6 121.6(4) . . ? C7 C8 C1 118.1(3) . . ? C7 C8 N2 123.4(3) . . ? C1 C8 N2 118.4(3) . . ? O1 C9 N2 124.1(3) . . ? O1 C9 C10 120.3(3) . . ? N2 C9 C10 115.5(3) . . ? C14 C10 C11 118.6(3) . . ? C14 C10 C9 124.4(3) . . ? C11 C10 C9 117.0(3) . . ? C10 C11 C12 119.5(3) . . ? N3 C12 C11 122.6(3) . . ? N3 C12 C12 117.3(4) . 3_655 ? C11 C12 C12 120.2(4) . 3_655 ? N3 C13 C14 123.7(4) . . ? C10 C14 C13 118.1(3) . . ? C19A N4 C15 113.8(6) . . ? C19A N4 C23 119.1(5) . . ? C15 N4 C23 107.0(2) . . ? C19A N4 C27 95.0(3) . . ? C15 N4 C27 111.1(3) . . ? C23 N4 C27 110.3(3) . . ? C19A N4 C19B 15.4(2) . . ? C15 N4 C19B 110.6(3) . . ? C23 N4 C19B 108.0(3) . . ? C27 N4 C19B 109.8(2) . . ? C16 C15 N4 116.3(3) . . ? C15 C16 C17 111.6(3) . . ? C16 C17 C18 113.2(4) . . ? N4 C19A C20A 97.4(4) . . ? C19A C20A C21A 111.2(5) . . ? C22A C21A C20A 109.2(6) . . ? C20B C19B N4 117.7(3) . . ? C19B C20B C21B 110.7(3) . . ? C22B C21B C20B 110.3(3) . . ? N4 C23 C24 115.1(3) . . ? C25 C24 C23 110.6(3) . . ? C26 C25 C24 111.9(4) . . ? C28 C27 N4 117.2(3) . . ? C27 C28 C29 111.1(2) . . ? C30 C29 C28 111.1(3) . . ? O3 C31 O2 124.6(4) . . ? O3 C31 C32 120.7(4) . . ? O2 C31 C32 114.4(4) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H901 O3 0.88 1.91 2.738(4) 155.0 . N2 H902 O2 0.88 1.90 2.757(4) 163.9 . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.209 _refine_diff_density_min -0.444 _refine_diff_density_rms 0.086 #===END # Attachment 'B912942A_CIF.cif' data_2009sot0305 _database_code_depnum_ccdc_archive 'CCDC 736407' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C60 H92 Cl2 N8 O2' _chemical_formula_weight 1028.32 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7760(3) _cell_length_b 18.4565(8) _cell_length_c 20.5069(9) _cell_angle_alpha 88.084(2) _cell_angle_beta 87.311(2) _cell_angle_gamma 86.759(3) _cell_volume 2933.8(2) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 50046 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Rod _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.164 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1116 _exptl_absorpt_coefficient_mu 0.159 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9499 _exptl_absorpt_correction_T_max 0.9921 _exptl_absorpt_process_details ; SADABS V2.10 (Sheldrick, G.M., 2003) ; _exptl_special_details ; SADABS was used to perform the Absorption correction Parameter refinement on 25142 reflections reduced R(int) from 0.1779 to 0.0879 Ratio of minimum to maximum apparent transmission: 0.815383 The given Tmin and Tmax were generated using the SHELX SIZE command ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating Anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 38808 _diffrn_reflns_av_R_equivalents 0.1701 _diffrn_reflns_av_sigmaI/netI 0.1407 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 25.03 _reflns_number_total 10236 _reflns_number_gt 6462 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'CAMERON (Watkin, et al., 1993)' _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The diffraction was weak and somewhat 'messy' resulting in a high R1 value. ; _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^)+(0.0001P)^2^+50.2227P] 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 SHELXL _refine_ls_extinction_coef 0.0020(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 10236 _refine_ls_number_parameters 658 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2253 _refine_ls_R_factor_gt 0.1623 _refine_ls_wR_factor_ref 0.3593 _refine_ls_wR_factor_gt 0.3290 _refine_ls_goodness_of_fit_ref 1.122 _refine_ls_restrained_S_all 1.122 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.3668(9) -0.3236(4) 0.3381(3) 0.0323(17) Uani 1 1 d . . . N1 N -0.1491(11) -0.4579(4) 0.1358(4) 0.033(2) Uani 1 1 d . . . H901 H -0.1651 -0.4953 0.1628 0.040 Uiso 1 1 calc R . . N2 N -0.2189(11) -0.4018(4) 0.2696(4) 0.0277(19) Uani 1 1 d . . . H902 H -0.1798 -0.4473 0.2663 0.033 Uiso 1 1 calc R . . N3 N -0.2892(11) -0.5442(5) 0.4842(4) 0.037(2) Uani 1 1 d . . . C1 C -0.1094(15) -0.4616(6) 0.0698(5) 0.039(3) Uani 1 1 d . . . H1 H -0.0948 -0.5051 0.0462 0.047 Uiso 1 1 calc R . . C2 C -0.0945(15) -0.3937(6) 0.0439(5) 0.042(3) Uani 1 1 d . . . H2 H -0.0663 -0.3814 -0.0006 0.051 Uiso 1 1 calc R . . C3 C -0.1290(12) -0.3436(6) 0.0957(5) 0.028(2) Uani 1 1 d . . . C4 C -0.1298(14) -0.2676(6) 0.0994(5) 0.034(2) Uani 1 1 d . . . H4 H -0.1108 -0.2378 0.0614 0.041 Uiso 1 1 calc R . . C5 C -0.1590(12) -0.2377(5) 0.1598(5) 0.027(2) Uani 1 1 d . . . H5 H -0.1574 -0.1865 0.1631 0.033 Uiso 1 1 calc R . . C6 C -0.1909(13) -0.2803(5) 0.2165(5) 0.031(2) Uani 1 1 d . . . H6 H -0.2114 -0.2574 0.2572 0.038 Uiso 1 1 calc R . . C7 C -0.1931(12) -0.3555(5) 0.2144(4) 0.024(2) Uani 1 1 d . . . C8 C -0.1595(12) -0.3871(5) 0.1527(5) 0.026(2) Uani 1 1 d . . . C9 C -0.2978(12) -0.3830(5) 0.3269(5) 0.025(2) Uani 1 1 d . . . C10 C -0.2942(13) -0.4414(5) 0.3808(5) 0.029(2) Uani 1 1 d . . . C11 C -0.4293(12) -0.4444(6) 0.4259(5) 0.028(2) Uani 1 1 d . . . H11 H -0.5253 -0.4105 0.4228 0.033 Uiso 1 1 calc R . . C12 C -0.4272(12) -0.4963(6) 0.4756(5) 0.028(2) Uani 1 1 d . . . C13 C -0.1573(14) -0.5397(6) 0.4409(5) 0.041(3) Uani 1 1 d . . . H13 H -0.0607 -0.5728 0.4462 0.049 Uiso 1 1 calc R . . C14 C -0.1499(13) -0.4911(6) 0.3893(5) 0.036(3) Uani 1 1 d . . . H14 H -0.0515 -0.4905 0.3600 0.043 Uiso 1 1 calc R . . O2 O -0.4147(9) 0.1668(4) 0.1603(3) 0.0302(16) Uani 1 1 d . . . N4 N -0.1608(10) 0.0344(4) 0.3620(4) 0.0287(19) Uani 1 1 d . . . H904 H -0.1744 -0.0035 0.3381 0.034 Uiso 1 1 calc R . . N5 N -0.2582(9) 0.0901(4) 0.2286(4) 0.0223(17) Uani 1 1 d . . . H905 H -0.2171 0.0449 0.2333 0.027 Uiso 1 1 calc R . . N6 N -0.3008(11) -0.0477(5) 0.0184(4) 0.031(2) Uani 1 1 d . . . C15 C -0.1096(14) 0.0319(7) 0.4247(5) 0.040(3) Uani 1 1 d . . . H15 H -0.0819 -0.0113 0.4495 0.048 Uiso 1 1 calc R . . C16 C -0.1040(14) 0.1010(6) 0.4465(5) 0.037(3) Uani 1 1 d . . . H16 H -0.0729 0.1138 0.4887 0.044 Uiso 1 1 calc R . . C17 C -0.1530(13) 0.1503(6) 0.3951(5) 0.033(2) Uani 1 1 d . . . C18 C -0.1713(13) 0.2243(5) 0.3882(5) 0.029(2) Uani 1 1 d . . . H18 H -0.1528 0.2539 0.4239 0.034 Uiso 1 1 calc R . . C19 C -0.2171(13) 0.2556(6) 0.3287(5) 0.034(2) Uani 1 1 d . . . H19 H -0.2259 0.3069 0.3234 0.041 Uiso 1 1 calc R . . C20 C -0.2516(12) 0.2112(5) 0.2748(5) 0.029(2) Uani 1 1 d . . . H20 H -0.2856 0.2336 0.2346 0.035 Uiso 1 1 calc R . . C21 C -0.2356(12) 0.1369(5) 0.2812(4) 0.025(2) Uani 1 1 d . . . C22 C -0.1877(12) 0.1056(5) 0.3421(5) 0.025(2) Uani 1 1 d . . . C23 C -0.3370(11) 0.1081(5) 0.1717(5) 0.024(2) Uani 1 1 d . . . C24 C -0.3227(13) 0.0505(6) 0.1205(4) 0.028(2) Uani 1 1 d . . . C25 C -0.1842(13) 0.0023(5) 0.1124(5) 0.029(2) Uani 1 1 d . . . H25 H -0.0917 0.0022 0.1411 0.035 Uiso 1 1 calc R . . C26 C -0.1788(14) -0.0457(5) 0.0630(5) 0.034(3) Uani 1 1 d . . . H26 H -0.0831 -0.0799 0.0597 0.040 Uiso 1 1 calc R . . C27 C -0.4345(12) 0.0005(5) 0.0252(4) 0.022(2) Uani 1 1 d . . . C28 C -0.4503(13) 0.0507(5) 0.0752(4) 0.027(2) Uani 1 1 d . . . H28 H -0.5470 0.0844 0.0782 0.032 Uiso 1 1 calc R . . N7 N -0.6812(10) -0.6274(4) 0.1828(4) 0.0257(18) Uani 1 1 d . . . C29 C -0.6376(12) -0.6669(5) 0.2480(5) 0.028(2) Uani 1 1 d . . . H29A H -0.5925 -0.7169 0.2386 0.034 Uiso 1 1 calc R . . H29B H -0.5441 -0.6418 0.2675 0.034 Uiso 1 1 calc R . . C30 C -0.7865(15) -0.6712(7) 0.2980(5) 0.044(3) Uani 1 1 d . . . H30A H -0.8712 -0.7046 0.2834 0.052 Uiso 1 1 calc R . . H30B H -0.8452 -0.6226 0.3031 0.052 Uiso 1 1 calc R . . C31 C -0.7154(15) -0.6993(7) 0.3637(5) 0.045(3) Uani 1 1 d . . . H31A H -0.6334 -0.7414 0.3559 0.054 Uiso 1 1 calc R . . H31B H -0.8118 -0.7162 0.3926 0.054 Uiso 1 1 calc R . . C32 C -0.6226(18) -0.6402(8) 0.3990(6) 0.062(4) Uani 1 1 d . . . H32A H -0.5269 -0.6234 0.3707 0.093 Uiso 1 1 calc R . . H32B H -0.5779 -0.6609 0.4399 0.093 Uiso 1 1 calc R . . H32C H -0.7045 -0.5993 0.4085 0.093 Uiso 1 1 calc R . . C33 C -0.7402(13) -0.5477(5) 0.1943(5) 0.031(2) Uani 1 1 d . . . H33A H -0.7611 -0.5237 0.1513 0.037 Uiso 1 1 calc R . . H33B H -0.8520 -0.5471 0.2195 0.037 Uiso 1 1 calc R . . C34 C -0.6200(13) -0.5027(5) 0.2295(6) 0.039(3) Uani 1 1 d . . . H34A H -0.5059 -0.5040 0.2059 0.047 Uiso 1 1 calc R . . H34B H -0.6043 -0.5237 0.2740 0.047 Uiso 1 1 calc R . . C35 C -0.6908(15) -0.4236(6) 0.2342(6) 0.043(3) Uani 1 1 d . . . H35A H -0.8112 -0.4233 0.2522 0.051 Uiso 1 1 calc R . . H35B H -0.6224 -0.3987 0.2653 0.051 Uiso 1 1 calc R . . C36 C -0.6876(17) -0.3811(6) 0.1698(6) 0.050(3) Uani 1 1 d . . . H36A H -0.5679 -0.3771 0.1535 0.075 Uiso 1 1 calc R . . H36B H -0.7416 -0.3325 0.1761 0.075 Uiso 1 1 calc R . . H36C H -0.7511 -0.4063 0.1380 0.075 Uiso 1 1 calc R . . C37 C -0.8314(13) -0.6601(6) 0.1530(5) 0.033(2) Uani 1 1 d . . . H37A H -0.9292 -0.6588 0.1857 0.040 Uiso 1 1 calc R . . H37B H -0.8664 -0.6283 0.1155 0.040 Uiso 1 1 calc R . . C38 C -0.8054(13) -0.7364(5) 0.1296(5) 0.030(2) Uani 1 1 d . . . H38A H -0.7673 -0.7693 0.1658 0.036 Uiso 1 1 calc R . . H38B H -0.7148 -0.7385 0.0940 0.036 Uiso 1 1 calc R . . C39 C -0.9734(14) -0.7604(6) 0.1049(6) 0.039(3) Uani 1 1 d . . . H39A H -1.0607 -0.7604 0.1416 0.047 Uiso 1 1 calc R . . H39B H -1.0147 -0.7246 0.0714 0.047 Uiso 1 1 calc R . . C40 C -0.9599(17) -0.8346(6) 0.0759(6) 0.048(3) Uani 1 1 d . . . H40A H -0.8796 -0.8344 0.0376 0.071 Uiso 1 1 calc R . . H40B H -1.0738 -0.8472 0.0628 0.071 Uiso 1 1 calc R . . H40C H -0.9174 -0.8705 0.1085 0.071 Uiso 1 1 calc R . . C41 C -0.5211(12) -0.6327(6) 0.1392(5) 0.032(2) Uani 1 1 d . . . H41A H -0.4250 -0.6154 0.1634 0.039 Uiso 1 1 calc R . . H41B H -0.4937 -0.6846 0.1305 0.039 Uiso 1 1 calc R . . C42 C -0.5260(13) -0.5919(6) 0.0749(5) 0.034(2) Uani 1 1 d . . . H42A H -0.5246 -0.5392 0.0820 0.041 Uiso 1 1 calc R . . H42B H -0.6337 -0.6011 0.0534 0.041 Uiso 1 1 calc R . . C43 C -0.3674(15) -0.6165(6) 0.0301(6) 0.042(3) Uani 1 1 d . . . H43A H -0.3559 -0.5811 -0.0070 0.050 Uiso 1 1 calc R . . H43B H -0.2619 -0.6159 0.0553 0.050 Uiso 1 1 calc R . . C44 C -0.3790(17) -0.6904(7) 0.0039(6) 0.052(3) Uani 1 1 d . . . H44A H -0.3763 -0.7266 0.0399 0.079 Uiso 1 1 calc R . . H44B H -0.2813 -0.7006 -0.0270 0.079 Uiso 1 1 calc R . . H44C H -0.4871 -0.6925 -0.0185 0.079 Uiso 1 1 calc R . . N8 N 0.3443(10) -0.1392(4) 0.3243(4) 0.0270(19) Uani 1 1 d . . . C45 C 0.4931(12) -0.1529(6) 0.3676(5) 0.030(2) Uani 1 1 d . . . H45A H 0.5903 -0.1254 0.3490 0.035 Uiso 1 1 calc R . . H45B H 0.5296 -0.2051 0.3661 0.035 Uiso 1 1 calc R . . C46 C 0.4630(13) -0.1335(6) 0.4390(5) 0.034(2) Uani 1 1 d . . . H46A H 0.3682 -0.1614 0.4592 0.041 Uiso 1 1 calc R . . H46B H 0.4290 -0.0811 0.4420 0.041 Uiso 1 1 calc R . . C47 C 0.6291(15) -0.1510(7) 0.4759(5) 0.044(3) Uani 1 1 d . . . H47A H 0.6530 -0.2043 0.4781 0.052 Uiso 1 1 calc R . . H47B H 0.7270 -0.1291 0.4515 0.052 Uiso 1 1 calc R . . C48 C 0.6155(18) -0.1236(9) 0.5424(6) 0.065(4) Uani 1 1 d . . . H48A H 0.5783 -0.0719 0.5409 0.098 Uiso 1 1 calc R . . H48B H 0.7282 -0.1297 0.5620 0.098 Uiso 1 1 calc R . . H48C H 0.5311 -0.1507 0.5688 0.098 Uiso 1 1 calc R . . C49 C 0.1919(13) -0.1846(5) 0.3467(5) 0.031(2) Uani 1 1 d . . . H49A H 0.1518 -0.1697 0.3910 0.037 Uiso 1 1 calc R . . H49B H 0.0964 -0.1725 0.3173 0.037 Uiso 1 1 calc R . . C50 C 0.2265(15) -0.2665(6) 0.3485(7) 0.048(3) Uani 1 1 d . . . H50A H 0.2578 -0.2829 0.3038 0.057 Uiso 1 1 calc R . . H50B H 0.3249 -0.2795 0.3763 0.057 Uiso 1 1 calc R . . C51 C 0.0697(16) -0.3045(7) 0.3750(6) 0.051(3) Uani 1 1 d . . . H51A H -0.0323 -0.2843 0.3520 0.061 Uiso 1 1 calc R . . H51B H 0.0855 -0.3566 0.3651 0.061 Uiso 1 1 calc R . . C52 C 0.035(2) -0.2981(7) 0.4451(6) 0.060(4) Uani 1 1 d . . . H52A H 0.1327 -0.3201 0.4685 0.090 Uiso 1 1 calc R . . H52B H -0.0695 -0.3234 0.4582 0.090 Uiso 1 1 calc R . . H52C H 0.0177 -0.2468 0.4556 0.090 Uiso 1 1 calc R . . C53 C 0.4159(12) -0.1601(6) 0.2562(4) 0.027(2) Uani 1 1 d . . . H53A H 0.5212 -0.1334 0.2459 0.033 Uiso 1 1 calc R . . H53B H 0.4505 -0.2126 0.2574 0.033 Uiso 1 1 calc R . . C54 C 0.2924(12) -0.1450(6) 0.2006(5) 0.033(2) Uani 1 1 d . . . H54A H 0.1951 -0.1774 0.2060 0.040 Uiso 1 1 calc R . . H54B H 0.2451 -0.0941 0.2018 0.040 Uiso 1 1 calc R . . C55 C 0.3891(14) -0.1581(6) 0.1357(5) 0.036(3) Uani 1 1 d . . . H55A H 0.4887 -0.1269 0.1316 0.043 Uiso 1 1 calc R . . H55B H 0.4343 -0.2093 0.1348 0.043 Uiso 1 1 calc R . . C56 C 0.2781(16) -0.1426(7) 0.0786(5) 0.046(3) Uani 1 1 d . . . H56A H 0.1835 -0.1757 0.0808 0.069 Uiso 1 1 calc R . . H56B H 0.3474 -0.1498 0.0379 0.069 Uiso 1 1 calc R . . H56C H 0.2306 -0.0924 0.0797 0.069 Uiso 1 1 calc R . . C57 C 0.2738(12) -0.0609(5) 0.3244(5) 0.028(2) Uani 1 1 d . . . H57A H 0.2255 -0.0503 0.3688 0.034 Uiso 1 1 calc R . . H57B H 0.1775 -0.0556 0.2944 0.034 Uiso 1 1 calc R . . C58 C 0.4049(13) -0.0030(5) 0.3043(6) 0.035(3) Uani 1 1 d . . . H58A H 0.4918 -0.0009 0.3378 0.042 Uiso 1 1 calc R . . H58B H 0.4653 -0.0153 0.2622 0.042 Uiso 1 1 calc R . . C59 C 0.3021(14) 0.0705(6) 0.2977(5) 0.037(3) Uani 1 1 d . . . H59A H 0.2204 0.0761 0.3360 0.045 Uiso 1 1 calc R . . H59B H 0.3828 0.1101 0.2981 0.045 Uiso 1 1 calc R . . C60 C 0.2037(16) 0.0779(6) 0.2366(6) 0.049(3) Uani 1 1 d . . . H60A H 0.2846 0.0761 0.1985 0.073 Uiso 1 1 calc R . . H60B H 0.1363 0.1244 0.2360 0.073 Uiso 1 1 calc R . . H60C H 0.1260 0.0381 0.2353 0.073 Uiso 1 1 calc R . . Cl1 Cl -0.1886(3) -0.57517(13) 0.24530(13) 0.0323(6) Uani 1 1 d . . . Cl2 Cl -0.1536(3) -0.08372(13) 0.26029(12) 0.0299(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 O1 0.036(4) 0.027(4) 0.032(4) -0.005(3) 0.009(3) 0.003(3) N1 0.041(5) 0.025(5) 0.034(5) 0.005(4) 0.001(4) -0.001(4) N2 0.038(5) 0.014(4) 0.029(5) 0.005(3) 0.003(4) 0.008(4) N3 0.034(5) 0.043(5) 0.031(5) 0.011(4) 0.006(4) 0.010(4) C1 0.055(7) 0.044(7) 0.020(5) -0.013(5) 0.012(5) -0.018(6) C2 0.051(7) 0.046(7) 0.031(6) 0.005(5) 0.008(5) -0.020(6) C3 0.025(5) 0.038(6) 0.023(5) 0.006(4) -0.001(4) -0.013(5) C4 0.047(7) 0.029(6) 0.027(6) 0.006(4) 0.002(5) -0.003(5) C5 0.025(5) 0.022(5) 0.035(6) 0.002(4) 0.003(4) -0.006(4) C6 0.032(6) 0.031(6) 0.030(6) 0.010(4) -0.004(4) 0.008(5) C7 0.021(5) 0.029(5) 0.021(5) 0.003(4) 0.000(4) -0.004(4) C8 0.022(5) 0.025(5) 0.030(5) -0.005(4) 0.001(4) 0.003(4) C9 0.023(5) 0.028(5) 0.025(5) 0.000(4) -0.001(4) 0.000(4) C10 0.030(6) 0.028(5) 0.028(5) -0.001(4) 0.005(4) 0.003(4) C11 0.020(5) 0.036(6) 0.025(5) 0.003(4) 0.001(4) 0.002(4) C12 0.024(5) 0.037(6) 0.024(5) 0.001(4) -0.001(4) 0.002(4) C13 0.038(6) 0.046(7) 0.033(6) 0.015(5) 0.005(5) 0.022(5) C14 0.022(5) 0.038(6) 0.046(7) 0.015(5) 0.000(5) 0.000(5) O2 0.033(4) 0.031(4) 0.027(4) -0.006(3) -0.009(3) 0.003(3) N4 0.033(5) 0.026(4) 0.027(5) 0.003(4) -0.001(4) 0.000(4) N5 0.022(4) 0.019(4) 0.026(4) -0.003(3) -0.003(3) 0.003(3) N6 0.029(5) 0.035(5) 0.028(5) -0.007(4) -0.006(4) 0.007(4) C15 0.038(6) 0.053(7) 0.026(6) 0.015(5) -0.009(5) 0.012(6) C16 0.043(7) 0.042(7) 0.025(6) -0.008(5) -0.007(5) 0.010(5) C17 0.032(6) 0.040(6) 0.026(5) -0.006(5) -0.002(4) -0.001(5) C18 0.045(6) 0.022(5) 0.020(5) -0.010(4) 0.003(4) -0.009(5) C19 0.038(6) 0.023(5) 0.044(7) -0.010(5) -0.001(5) -0.010(5) C20 0.026(5) 0.033(6) 0.027(5) 0.003(4) 0.002(4) 0.004(5) C21 0.024(5) 0.026(5) 0.024(5) -0.002(4) -0.004(4) -0.003(4) C22 0.016(5) 0.021(5) 0.037(6) -0.003(4) 0.000(4) 0.004(4) C23 0.014(5) 0.030(6) 0.029(5) -0.001(4) -0.007(4) -0.004(4) C24 0.037(6) 0.038(6) 0.008(4) 0.001(4) 0.000(4) -0.005(5) C25 0.026(5) 0.028(5) 0.032(6) 0.000(4) -0.011(4) 0.006(4) C26 0.037(6) 0.028(6) 0.036(6) -0.006(5) -0.016(5) 0.014(5) C27 0.023(5) 0.025(5) 0.018(5) 0.005(4) -0.002(4) -0.006(4) C28 0.030(5) 0.030(5) 0.021(5) 0.003(4) 0.001(4) 0.002(4) N7 0.022(4) 0.023(4) 0.033(5) -0.005(3) -0.004(3) -0.001(3) C29 0.015(5) 0.031(6) 0.039(6) 0.004(5) -0.011(4) 0.001(4) C30 0.044(7) 0.054(8) 0.030(6) 0.008(5) 0.005(5) 0.006(6) C31 0.040(7) 0.057(8) 0.037(6) 0.005(6) 0.008(5) -0.001(6) C32 0.063(9) 0.082(10) 0.044(8) -0.012(7) -0.024(7) 0.003(8) C33 0.025(5) 0.025(5) 0.043(6) -0.008(5) -0.006(5) 0.006(4) C34 0.019(5) 0.025(6) 0.073(8) -0.013(5) -0.004(5) -0.004(4) C35 0.038(7) 0.026(6) 0.065(8) -0.018(5) -0.017(6) 0.003(5) C36 0.054(8) 0.037(7) 0.060(8) -0.009(6) 0.000(6) -0.006(6) C37 0.022(5) 0.035(6) 0.044(6) -0.006(5) -0.001(5) -0.012(5) C38 0.031(6) 0.035(6) 0.025(5) 0.004(4) 0.004(4) -0.007(5) C39 0.036(6) 0.032(6) 0.052(7) -0.013(5) 0.001(5) -0.013(5) C40 0.059(8) 0.036(7) 0.050(7) -0.002(5) -0.018(6) -0.014(6) C41 0.020(5) 0.035(6) 0.043(6) -0.005(5) -0.006(4) 0.001(5) C42 0.028(6) 0.036(6) 0.038(6) -0.004(5) -0.001(5) 0.002(5) C43 0.039(7) 0.037(6) 0.047(7) 0.007(5) 0.009(5) 0.001(5) C44 0.054(8) 0.054(8) 0.048(8) -0.007(6) 0.011(6) -0.002(6) N8 0.020(4) 0.029(5) 0.032(5) 0.002(4) -0.006(3) 0.000(4) C45 0.013(5) 0.035(6) 0.040(6) 0.003(5) -0.002(4) 0.003(4) C46 0.029(6) 0.038(6) 0.035(6) -0.006(5) 0.000(5) -0.004(5) C47 0.038(7) 0.051(7) 0.043(7) -0.005(6) -0.003(5) -0.015(6) C48 0.061(9) 0.094(11) 0.045(8) -0.007(7) -0.022(7) -0.015(8) C49 0.030(6) 0.033(6) 0.030(6) -0.004(4) 0.002(4) -0.007(5) C50 0.035(7) 0.040(7) 0.069(9) -0.009(6) 0.015(6) -0.013(5) C51 0.046(7) 0.057(8) 0.050(8) -0.005(6) 0.003(6) -0.003(6) C52 0.086(11) 0.045(8) 0.049(8) 0.000(6) 0.010(7) -0.009(7) C53 0.021(5) 0.036(6) 0.024(5) -0.005(4) 0.004(4) -0.003(4) C54 0.019(5) 0.051(7) 0.030(6) -0.002(5) -0.008(4) 0.001(5) C55 0.036(6) 0.033(6) 0.039(6) -0.001(5) -0.002(5) -0.001(5) C56 0.056(8) 0.048(7) 0.035(6) -0.006(5) 0.001(6) -0.009(6) C57 0.017(5) 0.023(5) 0.044(6) -0.006(4) 0.003(4) 0.002(4) C58 0.027(6) 0.027(6) 0.052(7) 0.001(5) -0.003(5) -0.003(5) C59 0.030(6) 0.036(6) 0.045(7) -0.001(5) 0.012(5) -0.009(5) C60 0.046(7) 0.042(7) 0.055(8) 0.025(6) 0.000(6) 0.006(6) Cl1 0.0250(13) 0.0278(13) 0.0436(15) 0.0025(11) -0.0011(11) -0.0003(10) Cl2 0.0277(13) 0.0253(13) 0.0370(14) -0.0032(10) -0.0020(10) -0.0029(10) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C9 1.216(11) . ? N1 C8 1.361(12) . ? N1 C1 1.377(12) . ? N2 C9 1.347(12) . ? N2 C7 1.409(11) . ? N3 C13 1.330(13) . ? N3 C12 1.366(13) . ? C1 C2 1.354(15) . ? C2 C3 1.438(15) . ? C3 C4 1.406(14) . ? C3 C8 1.415(13) . ? C4 C5 1.376(14) . ? C5 C6 1.403(13) . ? C6 C7 1.391(14) . ? C7 C8 1.418(13) . ? C9 C10 1.518(13) . ? C10 C11 1.368(13) . ? C10 C14 1.422(14) . ? C11 C12 1.375(13) . ? C12 C12 1.485(19) 2_446 ? C13 C14 1.365(14) . ? O2 C23 1.232(11) . ? N4 C15 1.363(12) . ? N4 C22 1.371(12) . ? N5 C23 1.366(11) . ? N5 C21 1.428(12) . ? N6 C27 1.334(12) . ? N6 C26 1.350(12) . ? C15 C16 1.370(15) . ? C16 C17 1.420(14) . ? C17 C18 1.368(14) . ? C17 C22 1.430(14) . ? C18 C19 1.385(14) . ? C19 C20 1.442(14) . ? C20 C21 1.373(13) . ? C21 C22 1.417(13) . ? C23 C24 1.514(13) . ? C24 C25 1.366(14) . ? C24 C28 1.391(13) . ? C25 C26 1.366(14) . ? C27 C28 1.401(13) . ? C27 C27 1.487(17) 2_455 ? N7 C41 1.499(12) . ? N7 C37 1.508(12) . ? N7 C33 1.538(12) . ? N7 C29 1.545(12) . ? C29 C30 1.514(14) . ? C30 C31 1.543(15) . ? C31 C32 1.556(17) . ? C33 C34 1.509(13) . ? C34 C35 1.535(14) . ? C35 C36 1.513(16) . ? C37 C38 1.503(14) . ? C38 C39 1.517(14) . ? C39 C40 1.508(14) . ? C41 C42 1.497(14) . ? C42 C43 1.558(14) . ? C43 C44 1.492(16) . ? N8 C45 1.497(11) . ? N8 C57 1.518(12) . ? N8 C49 1.533(12) . ? N8 C53 1.534(12) . ? C45 C46 1.523(14) . ? C46 C47 1.540(15) . ? C47 C48 1.469(16) . ? C49 C50 1.519(15) . ? C50 C51 1.511(16) . ? C51 C52 1.456(16) . ? C53 C54 1.532(13) . ? C54 C55 1.518(14) . ? C55 C56 1.497(15) . ? C57 C58 1.550(13) . ? C58 C59 1.541(14) . ? C59 C60 1.498(15) . ? 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 C8 N1 C1 109.0(9) . . ? C9 N2 C7 126.1(8) . . ? C13 N3 C12 116.6(9) . . ? C2 C1 N1 109.5(9) . . ? C1 C2 C3 107.7(9) . . ? C4 C3 C8 120.2(9) . . ? C4 C3 C2 134.2(9) . . ? C8 C3 C2 105.5(9) . . ? C5 C4 C3 118.1(9) . . ? C4 C5 C6 122.1(9) . . ? C7 C6 C5 121.2(10) . . ? C6 C7 N2 124.3(9) . . ? C6 C7 C8 117.2(9) . . ? N2 C7 C8 118.4(8) . . ? N1 C8 C3 108.4(9) . . ? N1 C8 C7 130.5(9) . . ? C3 C8 C7 121.1(9) . . ? O1 C9 N2 125.0(9) . . ? O1 C9 C10 119.3(9) . . ? N2 C9 C10 115.7(8) . . ? C11 C10 C14 117.7(9) . . ? C11 C10 C9 119.6(9) . . ? C14 C10 C9 122.5(9) . . ? C10 C11 C12 120.4(9) . . ? N3 C12 C11 122.3(9) . . ? N3 C12 C12 115.0(11) . 2_446 ? C11 C12 C12 122.7(11) . 2_446 ? N3 C13 C14 125.2(10) . . ? C13 C14 C10 117.8(10) . . ? C15 N4 C22 108.7(9) . . ? C23 N5 C21 126.7(8) . . ? C27 N6 C26 116.1(8) . . ? N4 C15 C16 109.6(9) . . ? C15 C16 C17 108.2(9) . . ? C18 C17 C16 134.7(10) . . ? C18 C17 C22 120.2(9) . . ? C16 C17 C22 105.1(9) . . ? C17 C18 C19 119.5(9) . . ? C18 C19 C20 120.9(9) . . ? C21 C20 C19 120.3(9) . . ? C20 C21 C22 118.2(9) . . ? C20 C21 N5 123.0(8) . . ? C22 C21 N5 118.7(8) . . ? N4 C22 C21 130.8(9) . . ? N4 C22 C17 108.4(8) . . ? C21 C22 C17 120.9(9) . . ? O2 C23 N5 124.4(9) . . ? O2 C23 C24 120.0(8) . . ? N5 C23 C24 115.7(8) . . ? C25 C24 C28 117.5(9) . . ? C25 C24 C23 123.9(9) . . ? C28 C24 C23 118.3(9) . . ? C24 C25 C26 120.0(9) . . ? N6 C26 C25 124.2(9) . . ? N6 C27 C28 123.0(8) . . ? N6 C27 C27 115.7(10) . 2_455 ? C28 C27 C27 121.3(11) . 2_455 ? C24 C28 C27 119.2(9) . . ? C41 N7 C37 112.1(7) . . ? C41 N7 C33 111.1(8) . . ? C37 N7 C33 105.3(7) . . ? C41 N7 C29 107.0(7) . . ? C37 N7 C29 111.0(7) . . ? C33 N7 C29 110.5(7) . . ? C30 C29 N7 115.3(8) . . ? C29 C30 C31 108.6(9) . . ? C30 C31 C32 112.6(10) . . ? C34 C33 N7 117.1(8) . . ? C33 C34 C35 111.3(8) . . ? C36 C35 C34 114.2(10) . . ? C38 C37 N7 117.6(8) . . ? C37 C38 C39 109.4(8) . . ? C40 C39 C38 114.1(9) . . ? C42 C41 N7 117.0(8) . . ? C41 C42 C43 110.0(9) . . ? C44 C43 C42 113.6(10) . . ? C45 N8 C57 112.7(8) . . ? C45 N8 C49 111.6(7) . . ? C57 N8 C49 105.5(7) . . ? C45 N8 C53 104.8(7) . . ? C57 N8 C53 111.1(7) . . ? C49 N8 C53 111.3(7) . . ? N8 C45 C46 116.9(8) . . ? C45 C46 C47 109.7(8) . . ? C48 C47 C46 112.0(10) . . ? C50 C49 N8 116.3(8) . . ? C51 C50 C49 111.0(10) . . ? C52 C51 C50 114.5(11) . . ? C54 C53 N8 115.6(8) . . ? C55 C54 C53 109.3(8) . . ? C56 C55 C54 112.6(9) . . ? N8 C57 C58 115.9(7) . . ? C59 C58 C57 107.2(8) . . ? C60 C59 C58 112.8(9) . . ? 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 H901 Cl1 0.88 2.21 3.083(9) 168.7 . N2 H902 Cl1 0.88 2.42 3.249(8) 157.3 . N4 H904 Cl2 0.88 2.21 3.063(9) 163.9 . N5 H905 Cl2 0.88 2.45 3.315(8) 168.8 . _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.640 _refine_diff_density_min -0.425 _refine_diff_density_rms 0.114