# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_publication_text _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 #TrackingRef 'web_deposit_cif_file_0_BamaprasadBag_1322044159.4.cif' _publ_contact_author_name 'Bamaprasad Bag' _publ_contact_author_address ;Colloids and Materials Chemistry Department, Institute of Minerals and Materials Technology, CSIR-IMMT, P.O.: R.R.L., Bhubaneswar-751013 Odisha, India ; _publ_contact_author_email bpbag@immt.res.in _publ_contact_author_phone '+91 674 237 9254 ' _publ_contact_author_fax '+91 674 258 1637' loop_ _publ_author_address ;Colloids and Materials Chemistry Department, Institute of Minerals and Materials Technology, CSIR-IMMT, P.O.: R.R.L., Bhubaneswar-751013 Odisha, India ; '' _publ_author_name 'B. Bag' data_4 _database_code_depnum_ccdc_archive 'CCDC 855291' #TrackingRef 'web_deposit_cif_file_0_BamaprasadBag_1322044159.4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common p-nitrophenyl-amino-ethylene-amido-rhodamine _chemical_melting_point ? _chemical_formula_moiety 'C36 H39 N5 O4' _chemical_formula_sum 'C36 H39 N5 O4' _chemical_formula_weight 605.72 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 9.225(2) _cell_length_b 12.144(3) _cell_length_c 14.886(4) _cell_angle_alpha 74.73(1) _cell_angle_beta 78.29(2) _cell_angle_gamma 83.99(4) _cell_volume 1572.9(6) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle-shaped _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.279 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 644 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.5 _diffrn_reflns_number 26107 _diffrn_reflns_av_R_equivalents 0.0233 _diffrn_reflns_av_sigmaI/netI 0.0245 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.44 _diffrn_reflns_theta_max 28.35 _reflns_number_total 7814 _reflns_number_gt 5517 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Direct Methods (ShelXS)' _computing_cell_refinement 'Direct Methods (ShelXS)' _computing_data_reduction 'Direct Methods (ShelXS)' _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0873P)^2^+0.4817P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7814 _refine_ls_number_parameters 414 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0811 _refine_ls_R_factor_gt 0.0578 _refine_ls_wR_factor_ref 0.1844 _refine_ls_wR_factor_gt 0.1632 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 N1 N 0.1199(2) 1.26675(16) -0.08407(14) 0.0663(5) Uani 1 1 d . . . N2 N 0.5363(2) 0.56022(14) 0.22421(13) 0.0593(4) Uani 1 1 d . . . N3 N 0.29605(16) 1.03673(12) 0.32414(10) 0.0421(3) Uani 1 1 d . . . N4 N -0.00728(18) 0.83646(14) 0.44145(12) 0.0543(4) Uani 1 1 d . . . H4N H -0.0913 0.8658 0.4639 0.065 Uiso 1 1 calc R . . N5 N -0.0051(3) 0.41722(17) 0.35341(16) 0.0744(6) Uani 1 1 d . . . O1 O 0.36540(15) 0.93338(11) 0.07557(9) 0.0492(3) Uani 1 1 d . . . O2 O 0.29622(16) 1.10155(13) 0.45592(10) 0.0632(4) Uani 1 1 d . . . O3 O -0.1141(2) 0.35936(15) 0.38818(16) 0.0920(6) Uani 1 1 d . . . O4 O 0.1050(3) 0.3833(2) 0.30502(19) 0.1198(8) Uani 1 1 d . . . C1 C 0.49115(19) 0.82838(15) 0.30200(12) 0.0436(4) Uani 1 1 d . . . H1 H 0.5073 0.8535 0.3529 0.052 Uiso 1 1 calc R . . C2 C 0.5251(2) 0.71554(15) 0.30143(13) 0.0458(4) Uani 1 1 d . . . H2 H 0.5620 0.6660 0.3519 0.055 Uiso 1 1 calc R . . C3 C 0.50445(19) 0.67408(15) 0.22486(13) 0.0445(4) Uani 1 1 d . . . C4 C 0.4500(2) 0.75238(15) 0.15091(13) 0.0452(4) Uani 1 1 d . . . H4 H 0.4362 0.7285 0.0989 0.054 Uiso 1 1 calc R . . C5 C 0.2519(2) 1.20208(16) 0.14378(15) 0.0534(5) Uani 1 1 d . . . H5 H 0.2532 1.2378 0.1917 0.064 Uiso 1 1 calc R . . C6 C 0.1835(2) 1.25895(17) 0.06952(16) 0.0581(5) Uani 1 1 d . . . H6 H 0.1384 1.3312 0.0690 0.070 Uiso 1 1 calc R . . C7 C 0.1805(2) 1.20980(16) -0.00585(14) 0.0508(4) Uani 1 1 d . . . C8 C 0.2444(2) 1.09924(16) 0.00145(13) 0.0486(4) Uani 1 1 d . . . H8 H 0.2422 1.0625 -0.0457 0.058 Uiso 1 1 calc R . . C9 C 0.39419(18) 1.03064(14) 0.23257(12) 0.0397(4) Uani 1 1 d . . . C10 C 0.43345(17) 0.90663(14) 0.22926(11) 0.0380(3) Uani 1 1 d . . . C11 C 0.41600(18) 0.86526(14) 0.15398(11) 0.0398(4) Uani 1 1 d . . . C12 C 0.31965(19) 1.09246(14) 0.15000(12) 0.0415(4) Uani 1 1 d . . . C13 C 0.31100(19) 1.04314(14) 0.07771(12) 0.0415(4) Uani 1 1 d . . . C14 C 0.52969(19) 1.08703(14) 0.24022(13) 0.0431(4) Uani 1 1 d . . . C15 C 0.6613(2) 1.10731(16) 0.17669(16) 0.0557(5) Uani 1 1 d . . . H15 H 0.6740 1.0921 0.1174 0.067 Uiso 1 1 calc R . . C16 C 0.7743(2) 1.15101(18) 0.20370(19) 0.0671(6) Uani 1 1 d . . . H16 H 0.8642 1.1647 0.1621 0.081 Uiso 1 1 calc R . . C17 C 0.7554(2) 1.17448(18) 0.2916(2) 0.0680(6) Uani 1 1 d . . . H17 H 0.8331 1.2027 0.3085 0.082 Uiso 1 1 calc R . . C18 C 0.6224(2) 1.15646(17) 0.35448(17) 0.0594(5) Uani 1 1 d . . . H18 H 0.6088 1.1731 0.4132 0.071 Uiso 1 1 calc R . . C19 C 0.5095(2) 1.11275(14) 0.32728(13) 0.0457(4) Uani 1 1 d . . . C20 C 0.3578(2) 1.08492(15) 0.37864(13) 0.0457(4) Uani 1 1 d . . . C21 C 0.0456(4) 1.3799(2) -0.0919(2) 0.0922(9) Uani 1 1 d . . . H21B H 0.0947 1.4225 -0.0611 0.140(14) Uiso 1 1 calc R . . H21A H 0.0571 1.4198 -0.1584 0.127(12) Uiso 1 1 calc R . . C22 C -0.1112(5) 1.3799(4) -0.0509(4) 0.1499(17) Uani 1 1 d . . . H22A H -0.1598 1.3329 -0.0772 0.225 Uiso 1 1 calc R . . H22B H -0.1540 1.4566 -0.0650 0.225 Uiso 1 1 calc R . . H22C H -0.1235 1.3501 0.0165 0.225 Uiso 1 1 calc R . . C23 C 0.1212(3) 1.2124(2) -0.16082(16) 0.0664(6) Uani 1 1 d . . . H23A H 0.2171 1.1728 -0.1734 0.080 Uiso 1 1 calc R . . H23B H 0.1098 1.2715 -0.2176 0.080 Uiso 1 1 calc R . . C24 C 0.0033(3) 1.1293(3) -0.1417(2) 0.0908(8) Uani 1 1 d . . . H24A H 0.0096 1.0728 -0.0836 0.136 Uiso 1 1 calc R . . H24B H 0.0169 1.0926 -0.1928 0.136 Uiso 1 1 calc R . . H24C H -0.0923 1.1692 -0.1364 0.136 Uiso 1 1 calc R . . C25 C 0.5158(6) 0.5173(3) 0.1465(3) 0.153(2) Uani 1 1 d . . . H25A H 0.4284 0.5607 0.1268 0.183 Uiso 1 1 calc R . . H25B H 0.5980 0.5464 0.0965 0.183 Uiso 1 1 calc R . . C26 C 0.5035(10) 0.4270(5) 0.1375(5) 0.259(4) Uani 1 1 d . . . H26A H 0.4826 0.3746 0.1987 0.389 Uiso 1 1 calc R . . H26B H 0.5939 0.4019 0.1020 0.389 Uiso 1 1 calc R . . H26C H 0.4236 0.4298 0.1043 0.389 Uiso 1 1 calc R . . C27 C 0.6023(2) 0.48221(17) 0.29943(16) 0.0600(5) Uani 1 1 d . . . H27B H 0.6748 0.5221 0.3160 0.075(7) Uiso 1 1 calc R . . H27A H 0.6546 0.4192 0.2756 0.057(6) Uiso 1 1 calc R . . C28 C 0.4925(4) 0.4345(2) 0.3877(2) 0.0855(8) Uani 1 1 d . . . H28A H 0.4382 0.4962 0.4111 0.128 Uiso 1 1 calc R . . H28B H 0.5443 0.3872 0.4350 0.128 Uiso 1 1 calc R . . H28C H 0.4248 0.3896 0.3731 0.128 Uiso 1 1 calc R . . C29 C 0.14689(19) 0.99651(16) 0.34844(13) 0.0475(4) Uani 1 1 d . . . H29A H 0.1247 0.9748 0.2947 0.057 Uiso 1 1 calc R . . H29B H 0.0772 1.0588 0.3606 0.057 Uiso 1 1 calc R . . C30 C 0.1245(2) 0.89534(16) 0.43455(14) 0.0507(4) Uani 1 1 d . . . H30A H 0.2103 0.8421 0.4310 0.061 Uiso 1 1 calc R . . H30B H 0.1172 0.9221 0.4913 0.061 Uiso 1 1 calc R . . C31 C -0.0066(2) 0.73764(15) 0.41472(12) 0.0452(4) Uani 1 1 d . . . C32 C 0.1181(2) 0.69556(17) 0.35859(14) 0.0532(5) Uani 1 1 d . . . H32 H 0.2018 0.7382 0.3356 0.064 Uiso 1 1 calc R . . C33 C 0.1166(2) 0.59240(18) 0.33769(15) 0.0586(5) Uani 1 1 d . . . H33 H 0.1991 0.5654 0.3005 0.070 Uiso 1 1 calc R . . C34 C -0.0070(2) 0.52847(17) 0.37168(14) 0.0546(5) Uani 1 1 d . . . C35 C -0.1326(2) 0.56911(17) 0.42536(14) 0.0535(5) Uani 1 1 d . . . H35 H -0.2159 0.5259 0.4476 0.064 Uiso 1 1 calc R . . C36 C -0.1332(2) 0.67279(17) 0.44523(13) 0.0497(4) Uani 1 1 d . . . H36 H -0.2184 0.7009 0.4794 0.060 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 N1 0.0737(12) 0.0604(11) 0.0656(11) -0.0083(9) -0.0296(9) 0.0078(9) N2 0.0763(12) 0.0428(8) 0.0684(11) -0.0246(8) -0.0283(9) 0.0110(8) N3 0.0421(7) 0.0442(8) 0.0426(7) -0.0173(6) -0.0049(6) -0.0035(6) N4 0.0455(8) 0.0506(9) 0.0664(10) -0.0219(8) 0.0015(7) -0.0054(7) N5 0.1012(17) 0.0578(11) 0.0798(13) -0.0265(10) -0.0444(12) 0.0050(11) O1 0.0614(8) 0.0477(7) 0.0435(7) -0.0197(5) -0.0166(6) 0.0106(6) O2 0.0656(9) 0.0778(10) 0.0561(8) -0.0385(7) -0.0087(7) 0.0046(7) O3 0.1163(16) 0.0599(10) 0.1204(16) -0.0264(10) -0.0609(13) -0.0093(10) O4 0.141(2) 0.0901(14) 0.144(2) -0.0747(15) -0.0108(16) 0.0120(14) C1 0.0455(9) 0.0459(9) 0.0451(9) -0.0184(7) -0.0118(7) -0.0023(7) C2 0.0473(9) 0.0449(9) 0.0481(10) -0.0139(8) -0.0143(8) 0.0019(7) C3 0.0416(9) 0.0414(9) 0.0537(10) -0.0184(8) -0.0093(7) 0.0009(7) C4 0.0465(9) 0.0475(9) 0.0483(9) -0.0234(8) -0.0113(7) 0.0022(7) C5 0.0637(12) 0.0420(9) 0.0591(11) -0.0179(8) -0.0156(9) -0.0001(8) C6 0.0652(13) 0.0423(10) 0.0678(13) -0.0135(9) -0.0193(10) 0.0059(9) C7 0.0479(10) 0.0496(10) 0.0521(10) -0.0059(8) -0.0116(8) -0.0024(8) C8 0.0497(10) 0.0524(10) 0.0450(9) -0.0142(8) -0.0101(8) 0.0006(8) C9 0.0402(8) 0.0392(8) 0.0420(8) -0.0152(7) -0.0053(7) -0.0040(6) C10 0.0363(8) 0.0388(8) 0.0412(8) -0.0145(7) -0.0054(6) -0.0036(6) C11 0.0374(8) 0.0447(9) 0.0388(8) -0.0141(7) -0.0064(6) -0.0007(7) C12 0.0434(9) 0.0393(8) 0.0424(9) -0.0112(7) -0.0072(7) -0.0032(7) C13 0.0401(8) 0.0414(9) 0.0416(9) -0.0115(7) -0.0033(7) -0.0005(7) C14 0.0435(9) 0.0342(8) 0.0549(10) -0.0157(7) -0.0107(7) -0.0020(7) C15 0.0494(11) 0.0502(10) 0.0687(13) -0.0214(9) -0.0015(9) -0.0097(8) C16 0.0469(11) 0.0520(11) 0.1034(18) -0.0231(12) -0.0071(11) -0.0099(9) C17 0.0536(12) 0.0523(12) 0.1112(19) -0.0301(12) -0.0325(12) -0.0026(9) C18 0.0639(13) 0.0493(11) 0.0787(14) -0.0289(10) -0.0309(11) 0.0039(9) C19 0.0488(10) 0.0372(8) 0.0579(10) -0.0199(8) -0.0176(8) 0.0033(7) C20 0.0529(10) 0.0417(9) 0.0480(10) -0.0201(8) -0.0143(8) 0.0066(7) C21 0.116(2) 0.0707(16) 0.094(2) -0.0124(15) -0.0528(19) 0.0212(16) C22 0.110(3) 0.129(3) 0.225(5) -0.073(3) -0.045(3) 0.037(3) C23 0.0671(14) 0.0729(14) 0.0535(12) -0.0004(10) -0.0186(10) -0.0030(11) C24 0.0860(19) 0.0893(19) 0.103(2) -0.0117(16) -0.0430(17) -0.0123(15) C25 0.286(6) 0.0707(19) 0.158(3) -0.073(2) -0.148(4) 0.061(3) C26 0.465(13) 0.170(5) 0.243(7) -0.132(5) -0.230(8) 0.063(6) C27 0.0643(13) 0.0479(11) 0.0739(14) -0.0239(10) -0.0228(11) 0.0128(9) C28 0.108(2) 0.0609(14) 0.0818(17) -0.0132(13) -0.0114(15) -0.0027(14) C29 0.0419(9) 0.0539(10) 0.0475(10) -0.0155(8) -0.0060(7) -0.0025(7) C30 0.0523(10) 0.0506(10) 0.0514(10) -0.0159(8) -0.0092(8) -0.0051(8) C31 0.0455(9) 0.0464(9) 0.0432(9) -0.0101(7) -0.0087(7) -0.0013(7) C32 0.0465(10) 0.0571(11) 0.0559(11) -0.0177(9) -0.0048(8) -0.0024(8) C33 0.0577(12) 0.0613(12) 0.0605(12) -0.0241(10) -0.0132(9) 0.0088(9) C34 0.0716(13) 0.0470(10) 0.0530(11) -0.0164(8) -0.0275(10) 0.0039(9) C35 0.0582(11) 0.0562(11) 0.0497(10) -0.0092(8) -0.0193(9) -0.0113(9) C36 0.0455(10) 0.0560(11) 0.0479(10) -0.0137(8) -0.0067(8) -0.0053(8) _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 N1 C7 1.381(3) . ? N1 C21 1.457(3) . ? N1 C23 1.460(3) . ? N2 C3 1.385(2) . ? N2 C25 1.440(3) . ? N2 C27 1.456(3) . ? N3 C20 1.354(2) . ? N3 C29 1.452(2) . ? N3 C9 1.490(2) . ? N4 C31 1.359(2) . ? N4 C30 1.447(2) . ? N4 H4N 0.8600 . ? N5 O4 1.222(3) . ? N5 O3 1.233(3) . ? N5 C34 1.444(3) . ? O1 C11 1.377(2) . ? O1 C13 1.380(2) . ? O2 C20 1.233(2) . ? C1 C2 1.375(2) . ? C1 C10 1.395(2) . ? C1 H1 0.9300 . ? C2 C3 1.414(2) . ? C2 H2 0.9300 . ? C3 C4 1.393(3) . ? C4 C11 1.384(2) . ? C4 H4 0.9300 . ? C5 C6 1.373(3) . ? C5 C12 1.398(2) . ? C5 H5 0.9300 . ? C6 C7 1.409(3) . ? C6 H6 0.9300 . ? C7 C8 1.395(3) . ? C8 C13 1.385(2) . ? C8 H8 0.9300 . ? C9 C12 1.515(2) . ? C9 C10 1.523(2) . ? C9 C14 1.524(2) . ? C10 C11 1.386(2) . ? C12 C13 1.381(2) . ? C14 C15 1.379(3) . ? C14 C19 1.384(2) . ? C15 C16 1.389(3) . ? C15 H15 0.9300 . ? C16 C17 1.385(4) . ? C16 H16 0.9300 . ? C17 C18 1.383(3) . ? C17 H17 0.9300 . ? C18 C19 1.389(3) . ? C18 H18 0.9300 . ? C19 C20 1.478(3) . ? C21 C22 1.451(5) . ? C21 H21B 0.9700 . ? C21 H21A 0.9700 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 C24 1.494(3) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 C26 1.159(5) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 C28 1.507(4) . ? C27 H27B 0.9700 . ? C27 H27A 0.9700 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 C30 1.520(3) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 C36 1.407(3) . ? C31 C32 1.412(3) . ? C32 C33 1.370(3) . ? C32 H32 0.9300 . ? C33 C34 1.379(3) . ? C33 H33 0.9300 . ? C34 C35 1.392(3) . ? C35 C36 1.366(3) . ? C35 H35 0.9300 . ? C36 H36 0.9300 . ? 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 C7 N1 C21 122.2(2) . . ? C7 N1 C23 120.66(18) . . ? C21 N1 C23 117.05(19) . . ? C3 N2 C25 121.48(19) . . ? C3 N2 C27 120.42(16) . . ? C25 N2 C27 117.95(18) . . ? C20 N3 C29 124.85(15) . . ? C20 N3 C9 113.87(14) . . ? C29 N3 C9 121.26(13) . . ? C31 N4 C30 124.09(16) . . ? C31 N4 H4N 118.0 . . ? C30 N4 H4N 118.0 . . ? O4 N5 O3 122.3(2) . . ? O4 N5 C34 118.9(2) . . ? O3 N5 C34 118.7(2) . . ? C11 O1 C13 118.40(13) . . ? C2 C1 C10 122.54(15) . . ? C2 C1 H1 118.7 . . ? C10 C1 H1 118.7 . . ? C1 C2 C3 120.64(16) . . ? C1 C2 H2 119.7 . . ? C3 C2 H2 119.7 . . ? N2 C3 C4 121.76(16) . . ? N2 C3 C2 121.10(17) . . ? C4 C3 C2 117.13(15) . . ? C11 C4 C3 120.77(15) . . ? C11 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C6 C5 C12 122.45(18) . . ? C6 C5 H5 118.8 . . ? C12 C5 H5 118.8 . . ? C5 C6 C7 121.20(18) . . ? C5 C6 H6 119.4 . . ? C7 C6 H6 119.4 . . ? N1 C7 C8 120.71(18) . . ? N1 C7 C6 122.84(18) . . ? C8 C7 C6 116.45(17) . . ? C13 C8 C7 121.18(17) . . ? C13 C8 H8 119.4 . . ? C7 C8 H8 119.4 . . ? N3 C9 C12 110.54(13) . . ? N3 C9 C10 110.46(13) . . ? C12 C9 C10 109.97(13) . . ? N3 C9 C14 100.35(13) . . ? C12 C9 C14 114.65(14) . . ? C10 C9 C14 110.52(13) . . ? C11 C10 C1 116.18(15) . . ? C11 C10 C9 122.37(15) . . ? C1 C10 C9 121.44(14) . . ? O1 C11 C4 114.53(14) . . ? O1 C11 C10 122.76(15) . . ? C4 C11 C10 122.71(16) . . ? C13 C12 C5 115.92(16) . . ? C13 C12 C9 122.22(15) . . ? C5 C12 C9 121.83(15) . . ? O1 C13 C12 123.28(15) . . ? O1 C13 C8 114.00(15) . . ? C12 C13 C8 122.72(16) . . ? C15 C14 C19 120.83(17) . . ? C15 C14 C9 128.99(16) . . ? C19 C14 C9 110.08(15) . . ? C14 C15 C16 118.1(2) . . ? C14 C15 H15 120.9 . . ? C16 C15 H15 120.9 . . ? C17 C16 C15 121.1(2) . . ? C17 C16 H16 119.5 . . ? C15 C16 H16 119.5 . . ? C18 C17 C16 120.76(19) . . ? C18 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? C17 C18 C19 118.0(2) . . ? C17 C18 H18 121.0 . . ? C19 C18 H18 121.0 . . ? C14 C19 C18 121.13(19) . . ? C14 C19 C20 108.73(15) . . ? C18 C19 C20 130.14(18) . . ? O2 C20 N3 125.29(18) . . ? O2 C20 C19 127.94(17) . . ? N3 C20 C19 106.77(14) . . ? C22 C21 N1 114.6(3) . . ? C22 C21 H21B 108.6 . . ? N1 C21 H21B 108.6 . . ? C22 C21 H21A 108.6 . . ? N1 C21 H21A 108.6 . . ? H21B C21 H21A 107.6 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N1 C23 C24 114.6(2) . . ? N1 C23 H23A 108.6 . . ? C24 C23 H23A 108.6 . . ? N1 C23 H23B 108.6 . . ? C24 C23 H23B 108.6 . . ? H23A C23 H23B 107.6 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C26 C25 N2 134.1(5) . . ? C26 C25 H25A 103.7 . . ? N2 C25 H25A 103.7 . . ? C26 C25 H25B 103.7 . . ? N2 C25 H25B 103.7 . . ? H25A C25 H25B 105.3 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? N2 C27 C28 114.23(19) . . ? N2 C27 H27B 108.7 . . ? C28 C27 H27B 108.7 . . ? N2 C27 H27A 108.7 . . ? C28 C27 H27A 108.7 . . ? H27B C27 H27A 107.6 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? N3 C29 C30 113.50(15) . . ? N3 C29 H29A 108.9 . . ? C30 C29 H29A 108.9 . . ? N3 C29 H29B 108.9 . . ? C30 C29 H29B 108.9 . . ? H29A C29 H29B 107.7 . . ? N4 C30 C29 112.38(16) . . ? N4 C30 H30A 109.1 . . ? C29 C30 H30A 109.1 . . ? N4 C30 H30B 109.1 . . ? C29 C30 H30B 109.1 . . ? H30A C30 H30B 107.9 . . ? N4 C31 C36 119.32(16) . . ? N4 C31 C32 122.55(17) . . ? C36 C31 C32 118.12(17) . . ? C33 C32 C31 120.50(19) . . ? C33 C32 H32 119.7 . . ? C31 C32 H32 119.7 . . ? C32 C33 C34 120.13(19) . . ? C32 C33 H33 119.9 . . ? C34 C33 H33 119.9 . . ? C33 C34 C35 120.57(18) . . ? C33 C34 N5 119.8(2) . . ? C35 C34 N5 119.6(2) . . ? C36 C35 C34 119.75(18) . . ? C36 C35 H35 120.1 . . ? C34 C35 H35 120.1 . . ? C35 C36 C31 120.84(18) . . ? C35 C36 H36 119.6 . . ? C31 C36 H36 119.6 . . ? 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 C10 C1 C2 C3 0.9(3) . . . . ? C25 N2 C3 C4 0.5(4) . . . . ? C27 N2 C3 C4 175.92(18) . . . . ? C25 N2 C3 C2 -179.9(3) . . . . ? C27 N2 C3 C2 -4.5(3) . . . . ? C1 C2 C3 N2 -179.07(18) . . . . ? C1 C2 C3 C4 0.5(3) . . . . ? N2 C3 C4 C11 178.66(17) . . . . ? C2 C3 C4 C11 -0.9(3) . . . . ? C12 C5 C6 C7 -1.1(3) . . . . ? C21 N1 C7 C8 176.8(2) . . . . ? C23 N1 C7 C8 0.1(3) . . . . ? C21 N1 C7 C6 -4.0(3) . . . . ? C23 N1 C7 C6 179.3(2) . . . . ? C5 C6 C7 N1 -176.4(2) . . . . ? C5 C6 C7 C8 2.8(3) . . . . ? N1 C7 C8 C13 177.29(18) . . . . ? C6 C7 C8 C13 -2.0(3) . . . . ? C20 N3 C9 C12 -122.35(15) . . . . ? C29 N3 C9 C12 56.00(19) . . . . ? C20 N3 C9 C10 115.71(15) . . . . ? C29 N3 C9 C10 -65.94(19) . . . . ? C20 N3 C9 C14 -0.94(18) . . . . ? C29 N3 C9 C14 177.41(14) . . . . ? C2 C1 C10 C11 -1.9(3) . . . . ? C2 C1 C10 C9 178.88(16) . . . . ? N3 C9 C10 C11 128.92(16) . . . . ? C12 C9 C10 C11 6.6(2) . . . . ? C14 C9 C10 C11 -120.93(17) . . . . ? N3 C9 C10 C1 -51.9(2) . . . . ? C12 C9 C10 C1 -174.19(15) . . . . ? C14 C9 C10 C1 58.2(2) . . . . ? C13 O1 C11 C4 171.80(15) . . . . ? C13 O1 C11 C10 -9.0(2) . . . . ? C3 C4 C11 O1 179.06(15) . . . . ? C3 C4 C11 C10 -0.1(3) . . . . ? C1 C10 C11 O1 -177.61(15) . . . . ? C9 C10 C11 O1 1.6(2) . . . . ? C1 C10 C11 C4 1.5(2) . . . . ? C9 C10 C11 C4 -179.30(15) . . . . ? C6 C5 C12 C13 -1.4(3) . . . . ? C6 C5 C12 C9 -179.78(18) . . . . ? N3 C9 C12 C13 -130.45(16) . . . . ? C10 C9 C12 C13 -8.2(2) . . . . ? C14 C9 C12 C13 117.02(18) . . . . ? N3 C9 C12 C5 47.8(2) . . . . ? C10 C9 C12 C5 170.05(16) . . . . ? C14 C9 C12 C5 -64.7(2) . . . . ? C11 O1 C13 C12 7.4(2) . . . . ? C11 O1 C13 C8 -171.59(15) . . . . ? C5 C12 C13 O1 -176.64(16) . . . . ? C9 C12 C13 O1 1.7(3) . . . . ? C5 C12 C13 C8 2.3(3) . . . . ? C9 C12 C13 C8 -179.37(16) . . . . ? C7 C8 C13 O1 178.41(16) . . . . ? C7 C8 C13 C12 -0.6(3) . . . . ? N3 C9 C14 C15 179.90(18) . . . . ? C12 C9 C14 C15 -61.7(2) . . . . ? C10 C9 C14 C15 63.3(2) . . . . ? N3 C9 C14 C19 3.48(17) . . . . ? C12 C9 C14 C19 121.93(16) . . . . ? C10 C9 C14 C19 -113.12(16) . . . . ? C19 C14 C15 C16 1.9(3) . . . . ? C9 C14 C15 C16 -174.20(18) . . . . ? C14 C15 C16 C17 -0.5(3) . . . . ? C15 C16 C17 C18 -0.9(3) . . . . ? C16 C17 C18 C19 0.9(3) . . . . ? C15 C14 C19 C18 -1.9(3) . . . . ? C9 C14 C19 C18 174.82(16) . . . . ? C15 C14 C19 C20 178.53(16) . . . . ? C9 C14 C19 C20 -4.71(19) . . . . ? C17 C18 C19 C14 0.5(3) . . . . ? C17 C18 C19 C20 179.94(19) . . . . ? C29 N3 C20 O2 -0.2(3) . . . . ? C9 N3 C20 O2 178.06(17) . . . . ? C29 N3 C20 C19 179.98(15) . . . . ? C9 N3 C20 C19 -1.74(19) . . . . ? C14 C19 C20 O2 -175.78(18) . . . . ? C18 C19 C20 O2 4.7(3) . . . . ? C14 C19 C20 N3 4.02(19) . . . . ? C18 C19 C20 N3 -175.46(18) . . . . ? C7 N1 C21 C22 -87.5(4) . . . . ? C23 N1 C21 C22 89.4(4) . . . . ? C7 N1 C23 C24 79.6(3) . . . . ? C21 N1 C23 C24 -97.4(3) . . . . ? C3 N2 C25 C26 -160.5(8) . . . . ? C27 N2 C25 C26 24.0(10) . . . . ? C3 N2 C27 C28 82.6(3) . . . . ? C25 N2 C27 C28 -101.8(3) . . . . ? C20 N3 C29 C30 -65.8(2) . . . . ? C9 N3 C29 C30 116.06(17) . . . . ? C31 N4 C30 C29 100.5(2) . . . . ? N3 C29 C30 N4 -163.33(15) . . . . ? C30 N4 C31 C36 164.42(18) . . . . ? C30 N4 C31 C32 -14.3(3) . . . . ? N4 C31 C32 C33 176.40(19) . . . . ? C36 C31 C32 C33 -2.3(3) . . . . ? C31 C32 C33 C34 -0.2(3) . . . . ? C32 C33 C34 C35 1.7(3) . . . . ? C32 C33 C34 N5 -176.88(19) . . . . ? O4 N5 C34 C33 -2.5(3) . . . . ? O3 N5 C34 C33 176.7(2) . . . . ? O4 N5 C34 C35 178.9(2) . . . . ? O3 N5 C34 C35 -1.9(3) . . . . ? C33 C34 C35 C36 -0.6(3) . . . . ? N5 C34 C35 C36 178.01(18) . . . . ? C34 C35 C36 C31 -2.1(3) . . . . ? N4 C31 C36 C35 -175.31(18) . . . . ? C32 C31 C36 C35 3.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 28.35 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.022 _refine_diff_density_min -0.071 _refine_diff_density_rms 0.043