# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Zeng, Zhengzhi' _publ_contact_author_email zengzhzh@yahoo.com.cn _publ_section_title ; A Rhodamine-based Chemosensor for Cu2+ and Its Application in Bioimaging ; _publ_author_name 'Zhengzhi Zeng' # Attachment '- P-1.cif' data_p-1 _database_code_depnum_ccdc_archive 'CCDC 777719' #TrackingRef '- P-1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H30 N4 O3' _chemical_formula_weight 506.59 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.5265(6) _cell_length_b 11.3885(7) _cell_length_c 12.5521(7) _cell_angle_alpha 91.311(3) _cell_angle_beta 109.506(3) _cell_angle_gamma 94.149(3) _cell_volume 1278.68(13) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1570 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 24.91 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.31 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.316 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9680 _exptl_absorpt_correction_T_max 0.9738 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 7247 _diffrn_reflns_av_R_equivalents 0.0219 _diffrn_reflns_av_sigmaI/netI 0.0477 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4959 _reflns_number_gt 3164 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0583P)^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 SHELXL _refine_ls_extinction_coef 0.0063(18) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4959 _refine_ls_number_parameters 348 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0854 _refine_ls_R_factor_gt 0.0507 _refine_ls_wR_factor_ref 0.1415 _refine_ls_wR_factor_gt 0.1236 _refine_ls_goodness_of_fit_ref 1.164 _refine_ls_restrained_S_all 1.164 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C2 C 0.0954(2) 0.83955(16) 0.23607(15) 0.0331(5) Uani 1 1 d . . . C3 C 0.2042(2) 0.94003(17) 0.22785(15) 0.0336(5) Uani 1 1 d . . . C5 C 0.2173(2) 0.97170(17) 0.12591(15) 0.0337(5) Uani 1 1 d . . . C7 C -0.0233(2) 0.75562(17) -0.07966(16) 0.0383(5) Uani 1 1 d . . . H7 H -0.0089 0.7865 -0.1435 0.046 Uiso 1 1 calc R . . C8 C 0.0470(2) 0.81281(16) 0.02529(15) 0.0329(5) Uani 1 1 d . . . C9 C 0.0294(2) 0.77107(17) 0.12289(15) 0.0333(5) Uani 1 1 d . . . C10 C 0.2953(2) 1.00841(18) 0.32366(16) 0.0405(5) Uani 1 1 d . . . H10 H 0.2887 0.9897 0.3937 0.049 Uiso 1 1 calc R . . C12 C 0.3143(2) 1.06504(17) 0.11783(16) 0.0383(5) Uani 1 1 d . . . H12 H 0.3200 1.0834 0.0475 0.046 Uiso 1 1 calc R . . C13 C -0.0628(2) 0.66647(17) 0.10994(16) 0.0390(5) Uani 1 1 d . . . H13 H -0.0769 0.6363 0.1742 0.047 Uiso 1 1 calc R . . C14 C 0.3941(2) 1.10166(18) 0.32023(17) 0.0403(5) Uani 1 1 d . . . C15 C -0.1152(2) 0.65228(18) -0.09032(16) 0.0383(5) Uani 1 1 d . . . C18 C 0.3607(2) 0.70244(18) 0.28127(17) 0.0415(5) Uani 1 1 d . . . H18 H 0.3368 0.7522 0.2212 0.050 Uiso 1 1 calc R . . C19 C 0.4030(2) 1.13125(17) 0.21400(17) 0.0391(5) Uani 1 1 d . . . C21 C -0.0256(2) 0.83462(18) 0.37587(16) 0.0394(5) Uani 1 1 d . . . C22 C 0.4870(2) 0.63301(19) 0.30310(17) 0.0446(5) Uani 1 1 d . . . C23 C -0.0270(2) 0.88358(17) 0.27588(15) 0.0348(5) Uani 1 1 d . . . C24 C -0.1336(2) 0.60598(17) 0.00805(17) 0.0391(5) Uani 1 1 d . . . C25 C 0.0956(2) 0.75677(19) 0.41201(17) 0.0416(5) Uani 1 1 d . . . C26 C -0.1313(2) 0.96079(19) 0.22466(17) 0.0459(6) Uani 1 1 d . . . H26 H -0.1323 0.9945 0.1577 0.055 Uiso 1 1 calc R . . C27 C -0.2306(2) 0.49381(19) 0.00059(19) 0.0537(6) Uani 1 1 d . . . H27A H -0.2314 0.4758 0.0747 0.081 Uiso 1 1 calc R . . H27B H -0.1918 0.4305 -0.0298 0.081 Uiso 1 1 calc R . . H27C H -0.3306 0.5035 -0.0480 0.081 Uiso 1 1 calc R . . C28 C 0.4877(3) 1.1708(2) 0.42601(17) 0.0585(7) Uani 1 1 d . . . H28A H 0.4765 1.1329 0.4906 0.088 Uiso 1 1 calc R . . H28B H 0.4561 1.2491 0.4244 0.088 Uiso 1 1 calc R . . H28C H 0.5907 1.1748 0.4309 0.088 Uiso 1 1 calc R . . C29 C -0.1761(3) 0.6340(2) -0.30014(17) 0.0558(6) Uani 1 1 d . . . H29A H -0.1765 0.7191 -0.3015 0.067 Uiso 1 1 calc R . . H29B H -0.2622 0.6003 -0.3622 0.067 Uiso 1 1 calc R . . C30 C -0.2337(3) 0.9375(2) 0.3749(2) 0.0652(7) Uani 1 1 d . . . H30 H -0.3048 0.9559 0.4070 0.078 Uiso 1 1 calc R . . C31 C -0.1289(3) 0.8615(2) 0.42683(19) 0.0589(7) Uani 1 1 d . . . H31 H -0.1272 0.8289 0.4945 0.071 Uiso 1 1 calc R . . C32 C 0.5040(3) 1.2715(2) 0.1022(2) 0.0572(6) Uani 1 1 d . . . H32A H 0.5438 1.3534 0.1158 0.069 Uiso 1 1 calc R . . H32B H 0.4028 1.2690 0.0489 0.069 Uiso 1 1 calc R . . C33 C 0.6394(3) 0.5036(2) 0.3957(2) 0.0684(8) Uani 1 1 d . . . H33 H 0.6819 0.4477 0.4469 0.082 Uiso 1 1 calc R . . C34 C -0.0378(3) 0.5991(2) -0.3179(2) 0.0734(8) Uani 1 1 d . . . H34A H 0.0477 0.6278 -0.2544 0.110 Uiso 1 1 calc R . . H34B H -0.0301 0.6322 -0.3856 0.110 Uiso 1 1 calc R . . H34C H -0.0417 0.5147 -0.3253 0.110 Uiso 1 1 calc R . . C35 C 0.5929(3) 0.6276(3) 0.2544(2) 0.0707(8) Uani 1 1 d . . . H35 H 0.6011 0.6689 0.1934 0.085 Uiso 1 1 calc R . . C36 C -0.2341(3) 0.9868(2) 0.27501(19) 0.0610(7) Uani 1 1 d . . . H36 H -0.3053 1.0386 0.2413 0.073 Uiso 1 1 calc R . . C37 C 0.5969(3) 1.2054(2) 0.0496(2) 0.0740(8) Uani 1 1 d . . . H37A H 0.6982 1.2099 0.1004 0.111 Uiso 1 1 calc R . . H37B H 0.5943 1.2397 -0.0202 0.111 Uiso 1 1 calc R . . H37C H 0.5577 1.1244 0.0348 0.111 Uiso 1 1 calc R . . C38 C 0.6912(3) 0.5435(3) 0.3175(3) 0.0779(9) Uani 1 1 d . . . H38 H 0.7767 0.5215 0.3049 0.093 Uiso 1 1 calc R . . N1 N -0.1901(2) 0.59640(17) -0.19402(15) 0.0569(5) Uani 1 1 d . . . H1 H -0.2493 0.5350 -0.1964 0.068 Uiso 1 1 calc R . . N2 N 0.4991(2) 1.22564(16) 0.20706(15) 0.0537(5) Uani 1 1 d . . . H2 H 0.5596 1.2590 0.2692 0.064 Uiso 1 1 calc R . . N3 N 0.16368(17) 0.76163(14) 0.33016(12) 0.0355(4) Uani 1 1 d . . . N4 N 0.28238(18) 0.69439(14) 0.34584(13) 0.0391(4) Uani 1 1 d . . . O3 O 0.51280(17) 0.55726(14) 0.38973(13) 0.0596(5) Uani 1 1 d . . . O1 O 0.13528(16) 0.91371(12) 0.02420(10) 0.0429(4) Uani 1 1 d . . . O2 O 0.13344(18) 0.69943(15) 0.49574(13) 0.0636(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C2 0.0337(11) 0.0334(11) 0.0327(10) 0.0043(9) 0.0115(9) 0.0041(9) C3 0.0341(11) 0.0334(11) 0.0327(10) 0.0008(9) 0.0103(9) 0.0029(9) C5 0.0356(11) 0.0336(11) 0.0308(10) -0.0006(9) 0.0103(9) 0.0016(9) C7 0.0424(12) 0.0412(12) 0.0330(11) 0.0018(9) 0.0152(9) 0.0027(10) C8 0.0313(10) 0.0328(11) 0.0345(11) 0.0012(9) 0.0117(9) -0.0002(9) C9 0.0333(11) 0.0339(11) 0.0326(11) 0.0008(9) 0.0113(9) 0.0014(9) C10 0.0445(12) 0.0443(13) 0.0330(11) 0.0015(10) 0.0135(10) 0.0032(10) C12 0.0405(12) 0.0382(12) 0.0386(11) 0.0023(10) 0.0171(10) -0.0003(10) C13 0.0413(12) 0.0385(12) 0.0397(11) 0.0048(10) 0.0175(10) 0.0002(10) C14 0.0357(11) 0.0392(12) 0.0419(12) -0.0040(10) 0.0089(10) 0.0005(10) C15 0.0338(11) 0.0405(12) 0.0385(11) -0.0070(10) 0.0106(9) 0.0004(9) C18 0.0427(12) 0.0422(13) 0.0381(12) -0.0012(10) 0.0121(10) 0.0030(10) C19 0.0330(11) 0.0351(12) 0.0515(13) -0.0016(10) 0.0182(10) 0.0007(9) C21 0.0431(12) 0.0437(13) 0.0355(11) 0.0045(9) 0.0177(10) 0.0079(10) C22 0.0442(13) 0.0445(13) 0.0433(12) 0.0026(11) 0.0119(10) 0.0060(10) C23 0.0362(11) 0.0359(11) 0.0324(11) 0.0006(9) 0.0118(9) 0.0022(9) C24 0.0365(11) 0.0345(12) 0.0455(12) -0.0003(10) 0.0135(10) -0.0002(9) C25 0.0434(12) 0.0473(13) 0.0375(12) 0.0085(10) 0.0176(10) 0.0039(10) C26 0.0502(13) 0.0522(14) 0.0396(12) 0.0120(10) 0.0179(10) 0.0153(11) C27 0.0513(14) 0.0470(14) 0.0594(14) -0.0056(12) 0.0177(12) -0.0112(11) C28 0.0587(15) 0.0583(15) 0.0502(14) -0.0099(12) 0.0111(12) -0.0095(12) C29 0.0615(16) 0.0566(15) 0.0412(13) -0.0061(11) 0.0075(11) 0.0042(12) C30 0.0678(17) 0.0824(19) 0.0658(16) 0.0146(14) 0.0433(14) 0.0330(15) C31 0.0671(16) 0.0751(18) 0.0481(13) 0.0181(13) 0.0340(13) 0.0176(14) C32 0.0542(14) 0.0431(14) 0.0768(17) 0.0103(12) 0.0266(13) -0.0054(12) C33 0.0469(15) 0.0679(18) 0.0810(19) -0.0057(15) 0.0062(14) 0.0214(13) C34 0.087(2) 0.079(2) 0.0654(17) 0.0070(14) 0.0375(15) 0.0175(16) C35 0.0648(17) 0.085(2) 0.0758(18) 0.0065(16) 0.0406(15) 0.0092(16) C36 0.0608(16) 0.0715(17) 0.0611(15) 0.0196(13) 0.0270(13) 0.0349(14) C37 0.0723(18) 0.0764(19) 0.088(2) 0.0169(16) 0.0462(16) 0.0035(15) C38 0.0510(16) 0.087(2) 0.104(2) -0.0053(18) 0.0339(17) 0.0239(15) N1 0.0603(13) 0.0599(13) 0.0463(11) -0.0139(10) 0.0181(10) -0.0168(10) N2 0.0496(11) 0.0496(12) 0.0593(12) -0.0058(10) 0.0192(10) -0.0149(9) N3 0.0355(9) 0.0386(10) 0.0338(9) 0.0054(7) 0.0123(7) 0.0077(8) N4 0.0342(9) 0.0395(10) 0.0416(10) -0.0013(8) 0.0098(8) 0.0045(8) O3 0.0577(10) 0.0566(10) 0.0630(10) 0.0085(9) 0.0158(8) 0.0155(8) O1 0.0533(9) 0.0420(8) 0.0306(7) -0.0010(6) 0.0139(7) -0.0126(7) O2 0.0695(11) 0.0793(12) 0.0546(10) 0.0370(9) 0.0315(9) 0.0263(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C2 N3 1.491(2) . ? C2 C3 1.516(3) . ? C2 C9 1.518(2) . ? C2 C23 1.524(3) . ? C3 C5 1.380(3) . ? C3 C10 1.403(3) . ? C5 O1 1.377(2) . ? C5 C12 1.385(3) . ? C7 C8 1.384(3) . ? C7 C15 1.391(3) . ? C7 H7 0.9300 . ? C8 O1 1.377(2) . ? C8 C9 1.381(2) . ? C9 C13 1.401(3) . ? C10 C14 1.378(3) . ? C10 H10 0.9300 . ? C12 C19 1.387(3) . ? C12 H12 0.9300 . ? C13 C24 1.372(3) . ? C13 H13 0.9300 . ? C14 C19 1.411(3) . ? C14 C28 1.496(3) . ? C15 N1 1.373(2) . ? C15 C24 1.412(3) . ? C18 N4 1.272(2) . ? C18 C22 1.441(3) . ? C18 H18 0.9300 . ? C19 N2 1.384(2) . ? C21 C23 1.381(2) . ? C21 C31 1.388(3) . ? C21 C25 1.463(3) . ? C22 C35 1.347(3) . ? C22 O3 1.372(2) . ? C23 C26 1.379(3) . ? C24 C27 1.504(3) . ? C25 O2 1.214(2) . ? C25 N3 1.386(2) . ? C26 C36 1.375(3) . ? C26 H26 0.9300 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 N1 1.453(3) . ? C29 C34 1.487(3) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 C31 1.373(3) . ? C30 C36 1.384(3) . ? C30 H30 0.9300 . ? C31 H31 0.9300 . ? C32 N2 1.441(3) . ? C32 C37 1.500(3) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 C38 1.313(3) . ? C33 O3 1.373(3) . ? C33 H33 0.9300 . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 0.9600 . ? C35 C38 1.445(4) . ? C35 H35 0.9300 . ? C36 H36 0.9300 . ? C37 H37A 0.9600 . ? C37 H37B 0.9600 . ? C37 H37C 0.9600 . ? C38 H38 0.9300 . ? N1 H1 0.8600 . ? N2 H2 0.8600 . ? N3 N4 1.374(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 N3 C2 C3 112.64(15) . . ? N3 C2 C9 112.05(15) . . ? C3 C2 C9 109.85(15) . . ? N3 C2 C23 99.20(14) . . ? C3 C2 C23 111.62(15) . . ? C9 C2 C23 111.13(15) . . ? C5 C3 C10 115.87(18) . . ? C5 C3 C2 122.32(17) . . ? C10 C3 C2 121.79(17) . . ? O1 C5 C3 122.97(17) . . ? O1 C5 C12 114.57(16) . . ? C3 C5 C12 122.46(17) . . ? C8 C7 C15 120.52(18) . . ? C8 C7 H7 119.7 . . ? C15 C7 H7 119.7 . . ? O1 C8 C9 123.08(16) . . ? O1 C8 C7 114.71(16) . . ? C9 C8 C7 122.21(18) . . ? C8 C9 C13 116.12(17) . . ? C8 C9 C2 122.03(17) . . ? C13 C9 C2 121.67(16) . . ? C14 C10 C3 123.91(19) . . ? C14 C10 H10 118.0 . . ? C3 C10 H10 118.0 . . ? C5 C12 C19 120.41(18) . . ? C5 C12 H12 119.8 . . ? C19 C12 H12 119.8 . . ? C24 C13 C9 123.84(18) . . ? C24 C13 H13 118.1 . . ? C9 C13 H13 118.1 . . ? C10 C14 C19 118.20(18) . . ? C10 C14 C28 120.96(19) . . ? C19 C14 C28 120.83(19) . . ? N1 C15 C7 121.48(19) . . ? N1 C15 C24 119.75(18) . . ? C7 C15 C24 118.76(17) . . ? N4 C18 C22 118.7(2) . . ? N4 C18 H18 120.7 . . ? C22 C18 H18 120.7 . . ? N2 C19 C12 121.05(19) . . ? N2 C19 C14 119.81(18) . . ? C12 C19 C14 119.14(18) . . ? C23 C21 C31 121.0(2) . . ? C23 C21 C25 109.42(17) . . ? C31 C21 C25 129.58(19) . . ? C35 C22 O3 109.8(2) . . ? C35 C22 C18 132.1(2) . . ? O3 C22 C18 118.07(19) . . ? C26 C23 C21 120.46(18) . . ? C26 C23 C2 128.29(17) . . ? C21 C23 C2 111.25(17) . . ? C13 C24 C15 118.54(18) . . ? C13 C24 C27 120.93(18) . . ? C15 C24 C27 120.53(18) . . ? O2 C25 N3 125.35(19) . . ? O2 C25 C21 129.01(19) . . ? N3 C25 C21 105.64(17) . . ? C36 C26 C23 118.42(19) . . ? C36 C26 H26 120.8 . . ? C23 C26 H26 120.8 . . ? C24 C27 H27A 109.5 . . ? C24 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C24 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C14 C28 H28A 109.5 . . ? C14 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C14 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? N1 C29 C34 113.2(2) . . ? N1 C29 H29A 108.9 . . ? C34 C29 H29A 108.9 . . ? N1 C29 H29B 108.9 . . ? C34 C29 H29B 108.9 . . ? H29A C29 H29B 107.8 . . ? C31 C30 C36 120.4(2) . . ? C31 C30 H30 119.8 . . ? C36 C30 H30 119.8 . . ? C30 C31 C21 118.3(2) . . ? C30 C31 H31 120.8 . . ? C21 C31 H31 120.8 . . ? N2 C32 C37 113.8(2) . . ? N2 C32 H32A 108.8 . . ? C37 C32 H32A 108.8 . . ? N2 C32 H32B 108.8 . . ? C37 C32 H32B 108.8 . . ? H32A C32 H32B 107.7 . . ? C38 C33 O3 109.2(2) . . ? C38 C33 H33 125.4 . . ? O3 C33 H33 125.4 . . ? C29 C34 H34A 109.5 . . ? C29 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C29 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C22 C35 C38 105.0(2) . . ? C22 C35 H35 127.5 . . ? C38 C35 H35 127.5 . . ? C26 C36 C30 121.3(2) . . ? C26 C36 H36 119.3 . . ? C30 C36 H36 119.3 . . ? C32 C37 H37A 109.5 . . ? C32 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C32 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C33 C38 C35 108.5(2) . . ? C33 C38 H38 125.8 . . ? C35 C38 H38 125.8 . . ? C15 N1 C29 124.43(18) . . ? C15 N1 H1 117.8 . . ? C29 N1 H1 117.8 . . ? C19 N2 C32 124.06(18) . . ? C19 N2 H2 118.0 . . ? C32 N2 H2 118.0 . . ? N4 N3 C25 116.42(16) . . ? N4 N3 C2 129.09(15) . . ? C25 N3 C2 114.49(16) . . ? C18 N4 N3 120.61(17) . . ? C22 O3 C33 107.41(19) . . ? C8 O1 C5 118.50(14) . . ? 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 N3 C2 C3 C5 135.37(18) . . . . ? C9 C2 C3 C5 9.7(2) . . . . ? C23 C2 C3 C5 -114.0(2) . . . . ? N3 C2 C3 C10 -46.1(2) . . . . ? C9 C2 C3 C10 -171.80(17) . . . . ? C23 C2 C3 C10 64.5(2) . . . . ? C10 C3 C5 O1 -179.76(17) . . . . ? C2 C3 C5 O1 -1.2(3) . . . . ? C10 C3 C5 C12 0.0(3) . . . . ? C2 C3 C5 C12 178.62(17) . . . . ? C15 C7 C8 O1 179.73(17) . . . . ? C15 C7 C8 C9 -0.1(3) . . . . ? O1 C8 C9 C13 -179.27(17) . . . . ? C7 C8 C9 C13 0.6(3) . . . . ? O1 C8 C9 C2 5.7(3) . . . . ? C7 C8 C9 C2 -174.47(17) . . . . ? N3 C2 C9 C8 -137.84(18) . . . . ? C3 C2 C9 C8 -11.8(2) . . . . ? C23 C2 C9 C8 112.2(2) . . . . ? N3 C2 C9 C13 47.4(2) . . . . ? C3 C2 C9 C13 173.39(17) . . . . ? C23 C2 C9 C13 -62.6(2) . . . . ? C5 C3 C10 C14 -0.4(3) . . . . ? C2 C3 C10 C14 -178.97(18) . . . . ? O1 C5 C12 C19 179.68(17) . . . . ? C3 C5 C12 C19 -0.1(3) . . . . ? C8 C9 C13 C24 0.1(3) . . . . ? C2 C9 C13 C24 175.17(18) . . . . ? C3 C10 C14 C19 0.8(3) . . . . ? C3 C10 C14 C28 179.91(19) . . . . ? C8 C7 C15 N1 177.69(18) . . . . ? C8 C7 C15 C24 -1.0(3) . . . . ? C5 C12 C19 N2 -179.21(18) . . . . ? C5 C12 C19 C14 0.5(3) . . . . ? C10 C14 C19 N2 178.91(18) . . . . ? C28 C14 C19 N2 -0.2(3) . . . . ? C10 C14 C19 C12 -0.8(3) . . . . ? C28 C14 C19 C12 -179.97(19) . . . . ? N4 C18 C22 C35 -176.0(2) . . . . ? N4 C18 C22 O3 2.9(3) . . . . ? C31 C21 C23 C26 0.2(3) . . . . ? C25 C21 C23 C26 -179.82(18) . . . . ? C31 C21 C23 C2 -179.28(19) . . . . ? C25 C21 C23 C2 0.7(2) . . . . ? N3 C2 C23 C26 179.7(2) . . . . ? C3 C2 C23 C26 60.8(3) . . . . ? C9 C2 C23 C26 -62.2(3) . . . . ? N3 C2 C23 C21 -0.85(19) . . . . ? C3 C2 C23 C21 -119.78(18) . . . . ? C9 C2 C23 C21 117.20(18) . . . . ? C9 C13 C24 C15 -1.2(3) . . . . ? C9 C13 C24 C27 179.77(19) . . . . ? N1 C15 C24 C13 -177.09(18) . . . . ? C7 C15 C24 C13 1.6(3) . . . . ? N1 C15 C24 C27 1.9(3) . . . . ? C7 C15 C24 C27 -179.36(18) . . . . ? C23 C21 C25 O2 179.1(2) . . . . ? C31 C21 C25 O2 -0.9(4) . . . . ? C23 C21 C25 N3 -0.2(2) . . . . ? C31 C21 C25 N3 179.8(2) . . . . ? C21 C23 C26 C36 -0.5(3) . . . . ? C2 C23 C26 C36 178.8(2) . . . . ? C36 C30 C31 C21 -0.9(4) . . . . ? C23 C21 C31 C30 0.5(3) . . . . ? C25 C21 C31 C30 -179.5(2) . . . . ? O3 C22 C35 C38 -0.9(3) . . . . ? C18 C22 C35 C38 178.1(2) . . . . ? C23 C26 C36 C30 0.2(4) . . . . ? C31 C30 C36 C26 0.5(4) . . . . ? O3 C33 C38 C35 -0.8(3) . . . . ? C22 C35 C38 C33 1.1(3) . . . . ? C7 C15 N1 C29 3.3(3) . . . . ? C24 C15 N1 C29 -178.0(2) . . . . ? C34 C29 N1 C15 78.6(3) . . . . ? C12 C19 N2 C32 7.3(3) . . . . ? C14 C19 N2 C32 -172.5(2) . . . . ? C37 C32 N2 C19 -83.2(3) . . . . ? O2 C25 N3 N4 0.8(3) . . . . ? C21 C25 N3 N4 -179.86(15) . . . . ? O2 C25 N3 C2 -179.7(2) . . . . ? C21 C25 N3 C2 -0.3(2) . . . . ? C3 C2 N3 N4 -61.7(2) . . . . ? C9 C2 N3 N4 62.8(2) . . . . ? C23 C2 N3 N4 -179.84(17) . . . . ? C3 C2 N3 C25 118.88(18) . . . . ? C9 C2 N3 C25 -116.65(17) . . . . ? C23 C2 N3 C25 0.72(19) . . . . ? C22 C18 N4 N3 178.04(16) . . . . ? C25 N3 N4 C18 -172.96(17) . . . . ? C2 N3 N4 C18 7.6(3) . . . . ? C35 C22 O3 C33 0.4(3) . . . . ? C18 C22 O3 C33 -178.69(19) . . . . ? C38 C33 O3 C22 0.3(3) . . . . ? C9 C8 O1 C5 4.2(3) . . . . ? C7 C8 O1 C5 -175.64(16) . . . . ? C3 C5 O1 C8 -6.5(3) . . . . ? C12 C5 O1 C8 173.69(16) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.194 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.039