# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'RSC Advances' _journal_coden_cambridge 1500 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email xinhouliu@yahoo.cn _publ_contact_author_name 'Xinhou Liu' _publ_author_name 'Xinhou Liu' data_bo1121 _database_code_depnum_ccdc_archive 'CCDC 837247' #TrackingRef '- Chromophore A.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C35 H36 N4 O2' _chemical_formula_weight 544.68 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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.007(2) _cell_length_b 19.208(5) _cell_length_c 15.433(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.743(4) _cell_angle_gamma 90.00 _cell_volume 2923.4(12) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 5984 _cell_measurement_theta_min 3.09 _cell_measurement_theta_max 27.51 _exptl_crystal_description Prism _exptl_crystal_colour Blue _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.238 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1160 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9749 _exptl_absorpt_correction_T_max 0.9940 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type AFC10/Saturn724+ _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 22987 _diffrn_reflns_av_R_equivalents 0.1325 _diffrn_reflns_av_sigmaI/netI 0.1498 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 27.48 _reflns_number_total 6620 _reflns_number_gt 3154 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0066P)^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_number_reflns 6620 _refine_ls_number_parameters 376 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1432 _refine_ls_R_factor_gt 0.0618 _refine_ls_wR_factor_ref 0.1003 _refine_ls_wR_factor_gt 0.0869 _refine_ls_goodness_of_fit_ref 0.979 _refine_ls_restrained_S_all 0.979 _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 O1 O -0.00494(18) 0.38767(9) 0.61213(9) 0.0280(5) Uani 1 1 d . . . O2 O 0.55027(17) 0.16574(8) 0.75528(9) 0.0223(4) Uani 1 1 d . . . N1 N 0.7656(2) 0.06895(11) 0.52887(11) 0.0234(5) Uani 1 1 d . . . N2 N 0.2081(2) 0.23491(11) 0.83580(13) 0.0316(6) Uani 1 1 d . . . N3 N 0.0483(3) 0.36561(12) 0.92423(13) 0.0439(7) Uani 1 1 d . . . N4 N -0.1791(2) 0.50369(12) 0.72824(13) 0.0357(6) Uani 1 1 d . . . C1 C 0.7547(3) 0.02757(14) 0.44892(14) 0.0273(7) Uani 1 1 d . . . H1A H 0.7839 -0.0207 0.4647 0.033 Uiso 1 1 calc R . . H1B H 0.8168 0.0469 0.4115 0.033 Uiso 1 1 calc R . . C2 C 0.6130(3) 0.02615(13) 0.39726(15) 0.0240(6) Uani 1 1 d . . . H2A H 0.5581 -0.0079 0.4243 0.029 Uiso 1 1 calc R . . H2B H 0.6162 0.0105 0.3365 0.029 Uiso 1 1 calc R . . C3 C 0.5455(3) 0.09678(13) 0.39418(14) 0.0234(6) Uani 1 1 d . . . C4 C 0.5422(3) 0.11772(12) 0.48891(14) 0.0191(6) Uani 1 1 d . . . C5 C 0.4342(3) 0.14940(12) 0.51598(14) 0.0199(6) Uani 1 1 d . . . H5 H 0.3565 0.1595 0.4733 0.024 Uiso 1 1 calc R . . C6 C 0.4323(2) 0.16805(12) 0.60492(14) 0.0192(6) Uani 1 1 d . . . C7 C 0.5515(3) 0.15194(13) 0.66654(14) 0.0198(6) Uani 1 1 d . . . C8 C 0.6698(3) 0.12893(13) 0.64175(14) 0.0201(6) Uani 1 1 d . . . C9 C 0.6621(3) 0.10470(13) 0.55308(14) 0.0193(6) Uani 1 1 d . . . C10 C 0.8077(2) 0.13061(13) 0.70393(14) 0.0227(6) Uani 1 1 d . . . C11 C 0.9190(3) 0.12272(14) 0.64912(14) 0.0261(7) Uani 1 1 d . . . H11A H 0.9236 0.1655 0.6140 0.031 Uiso 1 1 calc R . . H11B H 1.0072 0.1171 0.6886 0.031 Uiso 1 1 calc R . . C12 C 0.8951(3) 0.06096(14) 0.58823(15) 0.0308(7) Uani 1 1 d . . . H12A H 0.9695 0.0573 0.5536 0.037 Uiso 1 1 calc R . . H12B H 0.8939 0.0177 0.6230 0.037 Uiso 1 1 calc R . . C13 C 0.4015(3) 0.09083(15) 0.34011(15) 0.0411(9) Uani 1 1 d . . . H13A H 0.3475 0.0588 0.3695 0.049 Uiso 1 1 calc R . . H13B H 0.4070 0.0731 0.2813 0.049 Uiso 1 1 calc R . . H13C H 0.3585 0.1368 0.3352 0.049 Uiso 1 1 calc R . . C14 C 0.6267(3) 0.15083(14) 0.35076(15) 0.0384(8) Uani 1 1 d . . . H14A H 0.5764 0.1948 0.3433 0.046 Uiso 1 1 calc R . . H14B H 0.6406 0.1336 0.2932 0.046 Uiso 1 1 calc R . . H14C H 0.7148 0.1585 0.3882 0.046 Uiso 1 1 calc R . . C15 C 0.8197(3) 0.07376(14) 0.77483(14) 0.0314(7) Uani 1 1 d . . . H15A H 0.7537 0.0826 0.8138 0.038 Uiso 1 1 calc R . . H15B H 0.9115 0.0742 0.8092 0.038 Uiso 1 1 calc R . . H15C H 0.8017 0.0282 0.7467 0.038 Uiso 1 1 calc R . . C16 C 0.8288(3) 0.20226(14) 0.74901(15) 0.0336(7) Uani 1 1 d . . . H16A H 0.7657 0.2075 0.7907 0.040 Uiso 1 1 calc R . . H16B H 0.8119 0.2390 0.7045 0.040 Uiso 1 1 calc R . . H16C H 0.9222 0.2058 0.7805 0.040 Uiso 1 1 calc R . . C17 C 0.3301(3) 0.20903(13) 0.63168(15) 0.0217(6) Uani 1 1 d . . . H17 H 0.3317 0.2123 0.6933 0.026 Uiso 1 1 calc R . . C18 C 0.2285(3) 0.24480(13) 0.57935(14) 0.0233(6) Uani 1 1 d . . . H18 H 0.2153 0.2367 0.5178 0.028 Uiso 1 1 calc R . . C19 C 0.0576(3) 0.34376(13) 0.55133(14) 0.0250(6) Uani 1 1 d . . . C20 C 0.1430(3) 0.29257(13) 0.61140(14) 0.0219(6) Uani 1 1 d . . . C21 C 0.1201(3) 0.30643(13) 0.69631(14) 0.0211(6) Uani 1 1 d . . . C22 C 0.0314(3) 0.36383(13) 0.69453(14) 0.0218(6) Uani 1 1 d . . . C23 C -0.0190(3) 0.39827(13) 0.76072(14) 0.0226(6) Uani 1 1 d . . . C24 C 0.1688(3) 0.26687(13) 0.77358(15) 0.0221(6) Uani 1 1 d . . . C25 C 0.0186(3) 0.37863(13) 0.85096(16) 0.0270(7) Uani 1 1 d . . . C26 C -0.1072(3) 0.45653(14) 0.74199(14) 0.0232(6) Uani 1 1 d . . . C27 C -0.0570(3) 0.30760(14) 0.49076(15) 0.0358(8) Uani 1 1 d . . . H27A H -0.1131 0.2818 0.5260 0.043 Uiso 1 1 calc R . . H27B H -0.0191 0.2753 0.4522 0.043 Uiso 1 1 calc R . . H27C H -0.1129 0.3425 0.4550 0.043 Uiso 1 1 calc R . . C28 C 0.1412(3) 0.39114(14) 0.50327(16) 0.0396(8) Uani 1 1 d . . . H28A H 0.0829 0.4275 0.4724 0.047 Uiso 1 1 calc R . . H28B H 0.1817 0.3639 0.4606 0.047 Uiso 1 1 calc R . . H28C H 0.2133 0.4128 0.5456 0.047 Uiso 1 1 calc R . . C29 C 0.4795(3) 0.11237(13) 0.79809(13) 0.0281(7) Uani 1 1 d . . . H29A H 0.4957 0.0658 0.7744 0.034 Uiso 1 1 calc R . . H29B H 0.3807 0.1214 0.7870 0.034 Uiso 1 1 calc R . . C30 C 0.5329(3) 0.11478(13) 0.89502(14) 0.0233(6) Uani 1 1 d . . . C31 C 0.5975(3) 0.05692(14) 0.93731(14) 0.0310(7) Uani 1 1 d . . . H31 H 0.6071 0.0158 0.9046 0.037 Uiso 1 1 calc R . . C32 C 0.6482(3) 0.05866(15) 1.02695(15) 0.0366(8) Uani 1 1 d . . . H32 H 0.6909 0.0187 1.0554 0.044 Uiso 1 1 calc R . . C33 C 0.6363(3) 0.11824(15) 1.07446(15) 0.0346(8) Uani 1 1 d . . . H33 H 0.6720 0.1197 1.1355 0.042 Uiso 1 1 calc R . . C34 C 0.5725(3) 0.17589(15) 1.03324(15) 0.0381(8) Uani 1 1 d . . . H34 H 0.5645 0.2172 1.0658 0.046 Uiso 1 1 calc R . . C35 C 0.5200(3) 0.17335(15) 0.94406(15) 0.0332(7) Uani 1 1 d . . . H35 H 0.4742 0.2129 0.9164 0.040 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 0.0301(11) 0.0321(11) 0.0213(8) 0.0007(8) 0.0031(8) 0.0114(9) O2 0.0214(10) 0.0284(11) 0.0172(8) -0.0007(8) 0.0037(7) -0.0033(9) N1 0.0196(13) 0.0308(14) 0.0198(10) -0.0023(10) 0.0041(10) 0.0042(11) N2 0.0273(14) 0.0385(16) 0.0291(11) 0.0020(11) 0.0051(11) 0.0059(12) N3 0.0564(19) 0.0479(17) 0.0284(12) 0.0007(12) 0.0101(12) 0.0187(15) N4 0.0346(16) 0.0360(15) 0.0361(12) -0.0038(12) 0.0047(12) 0.0082(13) C1 0.0251(16) 0.0321(17) 0.0257(13) -0.0036(13) 0.0079(12) 0.0019(13) C2 0.0251(15) 0.0259(16) 0.0225(12) -0.0014(12) 0.0080(12) 0.0003(13) C3 0.0243(16) 0.0243(16) 0.0226(12) -0.0017(12) 0.0065(12) 0.0018(13) C4 0.0197(15) 0.0190(14) 0.0183(12) -0.0008(11) 0.0025(11) -0.0023(12) C5 0.0185(14) 0.0222(15) 0.0189(12) 0.0020(11) 0.0031(11) 0.0002(12) C6 0.0165(14) 0.0233(15) 0.0183(12) -0.0001(11) 0.0042(11) 0.0026(12) C7 0.0213(15) 0.0226(15) 0.0161(12) -0.0008(11) 0.0049(11) -0.0015(12) C8 0.0193(15) 0.0228(15) 0.0180(12) 0.0017(11) 0.0024(11) -0.0004(12) C9 0.0156(14) 0.0186(14) 0.0252(13) 0.0021(12) 0.0075(12) 0.0002(11) C10 0.0172(15) 0.0270(16) 0.0230(12) -0.0026(12) 0.0006(12) -0.0015(12) C11 0.0196(15) 0.0351(17) 0.0227(12) 0.0021(13) 0.0013(12) -0.0021(13) C12 0.0170(15) 0.0476(19) 0.0279(13) 0.0004(14) 0.0045(12) 0.0052(14) C13 0.0337(19) 0.058(2) 0.0280(14) -0.0149(15) -0.0042(14) 0.0128(16) C14 0.056(2) 0.0360(18) 0.0275(14) 0.0018(13) 0.0192(14) 0.0053(17) C15 0.0241(17) 0.0431(19) 0.0254(13) 0.0030(13) 0.0000(12) 0.0040(14) C16 0.0190(16) 0.0449(19) 0.0351(14) -0.0060(14) -0.0001(13) -0.0037(14) C17 0.0229(15) 0.0218(15) 0.0213(12) -0.0018(12) 0.0059(11) -0.0039(12) C18 0.0234(16) 0.0270(16) 0.0191(12) -0.0030(12) 0.0023(12) 0.0039(13) C19 0.0300(17) 0.0265(16) 0.0196(12) -0.0011(12) 0.0075(12) 0.0123(14) C20 0.0157(14) 0.0249(15) 0.0243(13) -0.0011(12) 0.0017(11) -0.0002(12) C21 0.0185(15) 0.0229(15) 0.0208(12) -0.0003(12) -0.0003(11) 0.0015(12) C22 0.0184(15) 0.0237(15) 0.0210(13) -0.0006(12) -0.0033(12) -0.0014(12) C23 0.0197(15) 0.0258(16) 0.0217(13) -0.0026(12) 0.0017(12) 0.0010(12) C24 0.0166(15) 0.0253(15) 0.0241(13) -0.0096(13) 0.0030(12) -0.0010(12) C25 0.0256(16) 0.0262(16) 0.0313(14) -0.0036(13) 0.0109(13) 0.0027(13) C26 0.0223(16) 0.0284(16) 0.0184(13) -0.0030(12) 0.0020(12) -0.0014(13) C27 0.0342(18) 0.0376(18) 0.0319(14) -0.0053(14) -0.0047(14) 0.0146(15) C28 0.047(2) 0.0394(19) 0.0343(15) 0.0080(15) 0.0134(15) 0.0094(17) C29 0.0299(17) 0.0343(17) 0.0210(12) 0.0038(13) 0.0067(12) -0.0104(14) C30 0.0223(15) 0.0265(15) 0.0213(12) 0.0011(12) 0.0045(12) -0.0025(13) C31 0.0371(19) 0.0295(17) 0.0259(14) -0.0015(13) 0.0037(13) -0.0015(14) C32 0.042(2) 0.0387(19) 0.0291(15) 0.0121(14) 0.0067(14) 0.0097(16) C33 0.0369(19) 0.045(2) 0.0223(13) -0.0014(14) 0.0062(13) 0.0117(16) C34 0.041(2) 0.046(2) 0.0264(15) -0.0089(14) 0.0032(14) 0.0138(16) C35 0.0336(18) 0.0384(18) 0.0268(14) 0.0016(14) 0.0029(13) 0.0107(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C22 1.342(2) . ? O1 C19 1.477(3) . ? O2 C7 1.397(2) . ? O2 C29 1.465(3) . ? N1 C9 1.347(3) . ? N1 C1 1.456(3) . ? N1 C12 1.462(3) . ? N2 C24 1.151(3) . ? N3 C25 1.147(3) . ? N4 C26 1.154(3) . ? C1 C2 1.505(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.513(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.522(3) . ? C3 C14 1.540(3) . ? C3 C13 1.542(3) . ? C4 C5 1.366(3) . ? C4 C9 1.442(3) . ? C5 C6 1.422(3) . ? C5 H5 0.9500 . ? C6 C17 1.406(3) . ? C6 C7 1.428(3) . ? C7 C8 1.377(3) . ? C8 C9 1.435(3) . ? C8 C10 1.542(3) . ? C10 C11 1.516(3) . ? C10 C15 1.536(3) . ? C10 C16 1.540(3) . ? C11 C12 1.507(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.371(3) . ? C17 H17 0.9500 . ? C18 C20 1.400(3) . ? C18 H18 0.9500 . ? C19 C20 1.513(3) . ? C19 C28 1.513(3) . ? C19 C27 1.520(3) . ? C20 C21 1.394(3) . ? C21 C22 1.413(3) . ? C21 C24 1.428(3) . ? C22 C23 1.382(3) . ? C23 C26 1.424(3) . ? C23 C25 1.430(3) . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 C30 1.502(3) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 C35 1.374(3) . ? C30 C31 1.392(3) . ? C31 C32 1.391(3) . ? C31 H31 0.9500 . ? C32 C33 1.375(4) . ? C32 H32 0.9500 . ? C33 C34 1.379(3) . ? C33 H33 0.9500 . ? C34 C35 1.389(3) . ? C34 H34 0.9500 . ? C35 H35 0.9500 . ? 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 C22 O1 C19 109.32(18) . . ? C7 O2 C29 113.22(17) . . ? C9 N1 C1 124.2(2) . . ? C9 N1 C12 121.38(19) . . ? C1 N1 C12 113.9(2) . . ? N1 C1 C2 112.8(2) . . ? N1 C1 H1A 109.0 . . ? C2 C1 H1A 109.0 . . ? N1 C1 H1B 109.0 . . ? C2 C1 H1B 109.0 . . ? H1A C1 H1B 107.8 . . ? C1 C2 C3 112.1(2) . . ? C1 C2 H2A 109.2 . . ? C3 C2 H2A 109.2 . . ? C1 C2 H2B 109.2 . . ? C3 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? C2 C3 C4 106.79(19) . . ? C2 C3 C14 110.6(2) . . ? C4 C3 C14 109.8(2) . . ? C2 C3 C13 108.8(2) . . ? C4 C3 C13 111.7(2) . . ? C14 C3 C13 109.1(2) . . ? C5 C4 C9 118.5(2) . . ? C5 C4 C3 123.9(2) . . ? C9 C4 C3 117.6(2) . . ? C4 C5 C6 123.2(2) . . ? C4 C5 H5 118.4 . . ? C6 C5 H5 118.4 . . ? C17 C6 C5 123.6(2) . . ? C17 C6 C7 119.5(2) . . ? C5 C6 C7 116.2(2) . . ? C8 C7 O2 118.9(2) . . ? C8 C7 C6 123.0(2) . . ? O2 C7 C6 117.8(2) . . ? C7 C8 C9 117.3(2) . . ? C7 C8 C10 122.8(2) . . ? C9 C8 C10 119.9(2) . . ? N1 C9 C8 120.7(2) . . ? N1 C9 C4 119.2(2) . . ? C8 C9 C4 120.2(2) . . ? C11 C10 C15 110.5(2) . . ? C11 C10 C16 106.5(2) . . ? C15 C10 C16 108.97(18) . . ? C11 C10 C8 108.38(18) . . ? C15 C10 C8 112.5(2) . . ? C16 C10 C8 109.9(2) . . ? C12 C11 C10 111.9(2) . . ? C12 C11 H11A 109.2 . . ? C10 C11 H11A 109.2 . . ? C12 C11 H11B 109.2 . . ? C10 C11 H11B 109.2 . . ? H11A C11 H11B 107.9 . . ? N1 C12 C11 109.8(2) . . ? N1 C12 H12A 109.7 . . ? C11 C12 H12A 109.7 . . ? N1 C12 H12B 109.7 . . ? C11 C12 H12B 109.7 . . ? H12A C12 H12B 108.2 . . ? C3 C13 H13A 109.5 . . ? C3 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C3 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C3 C14 H14A 109.5 . . ? C3 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C3 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C10 C15 H15A 109.5 . . ? C10 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C10 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C10 C16 H16A 109.5 . . ? C10 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C10 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 C6 127.7(2) . . ? C18 C17 H17 116.2 . . ? C6 C17 H17 116.2 . . ? C17 C18 C20 123.8(2) . . ? C17 C18 H18 118.1 . . ? C20 C18 H18 118.1 . . ? O1 C19 C20 103.77(17) . . ? O1 C19 C28 107.3(2) . . ? C20 C19 C28 112.9(2) . . ? O1 C19 C27 107.1(2) . . ? C20 C19 C27 111.7(2) . . ? C28 C19 C27 113.3(2) . . ? C21 C20 C18 131.7(2) . . ? C21 C20 C19 106.6(2) . . ? C18 C20 C19 121.7(2) . . ? C20 C21 C22 109.5(2) . . ? C20 C21 C24 126.6(2) . . ? C22 C21 C24 123.8(2) . . ? O1 C22 C23 117.6(2) . . ? O1 C22 C21 110.7(2) . . ? C23 C22 C21 131.7(2) . . ? C22 C23 C26 121.1(2) . . ? C22 C23 C25 121.6(2) . . ? C26 C23 C25 117.2(2) . . ? N2 C24 C21 179.9(3) . . ? N3 C25 C23 177.3(3) . . ? N4 C26 C23 178.9(3) . . ? C19 C27 H27A 109.5 . . ? C19 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C19 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C19 C28 H28A 109.5 . . ? C19 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C19 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? O2 C29 C30 108.07(19) . . ? O2 C29 H29A 110.1 . . ? C30 C29 H29A 110.1 . . ? O2 C29 H29B 110.1 . . ? C30 C29 H29B 110.1 . . ? H29A C29 H29B 108.4 . . ? C35 C30 C31 118.4(2) . . ? C35 C30 C29 121.6(2) . . ? C31 C30 C29 120.1(2) . . ? C32 C31 C30 120.6(2) . . ? C32 C31 H31 119.7 . . ? C30 C31 H31 119.7 . . ? C33 C32 C31 120.0(3) . . ? C33 C32 H32 120.0 . . ? C31 C32 H32 120.0 . . ? C32 C33 C34 119.8(2) . . ? C32 C33 H33 120.1 . . ? C34 C33 H33 120.1 . . ? C33 C34 C35 119.8(3) . . ? C33 C34 H34 120.1 . . ? C35 C34 H34 120.1 . . ? C30 C35 C34 121.3(3) . . ? C30 C35 H35 119.3 . . ? C34 C35 H35 119.3 . . ? 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 C9 N1 C1 C2 -2.5(3) . . . . ? C12 N1 C1 C2 169.3(2) . . . . ? N1 C1 C2 C3 41.5(3) . . . . ? C1 C2 C3 C4 -59.4(3) . . . . ? C1 C2 C3 C14 60.0(3) . . . . ? C1 C2 C3 C13 179.9(2) . . . . ? C2 C3 C4 C5 -139.2(2) . . . . ? C14 C3 C4 C5 100.9(3) . . . . ? C13 C3 C4 C5 -20.4(4) . . . . ? C2 C3 C4 C9 42.4(3) . . . . ? C14 C3 C4 C9 -77.5(3) . . . . ? C13 C3 C4 C9 161.3(2) . . . . ? C9 C4 C5 C6 -2.3(4) . . . . ? C3 C4 C5 C6 179.4(2) . . . . ? C4 C5 C6 C17 170.9(2) . . . . ? C4 C5 C6 C7 0.1(4) . . . . ? C29 O2 C7 C8 -105.4(3) . . . . ? C29 O2 C7 C6 79.7(3) . . . . ? C17 C6 C7 C8 -162.1(2) . . . . ? C5 C6 C7 C8 9.0(4) . . . . ? C17 C6 C7 O2 12.5(3) . . . . ? C5 C6 C7 O2 -176.3(2) . . . . ? O2 C7 C8 C9 170.2(2) . . . . ? C6 C7 C8 C9 -15.2(4) . . . . ? O2 C7 C8 C10 -11.8(4) . . . . ? C6 C7 C8 C10 162.9(2) . . . . ? C1 N1 C9 C8 163.6(2) . . . . ? C12 N1 C9 C8 -7.6(4) . . . . ? C1 N1 C9 C4 -15.7(4) . . . . ? C12 N1 C9 C4 173.1(2) . . . . ? C7 C8 C9 N1 -166.8(2) . . . . ? C10 C8 C9 N1 15.2(4) . . . . ? C7 C8 C9 C4 12.5(4) . . . . ? C10 C8 C9 C4 -165.6(2) . . . . ? C5 C4 C9 N1 175.2(2) . . . . ? C3 C4 C9 N1 -6.4(4) . . . . ? C5 C4 C9 C8 -4.1(4) . . . . ? C3 C4 C9 C8 174.4(2) . . . . ? C7 C8 C10 C11 -163.2(2) . . . . ? C9 C8 C10 C11 14.8(3) . . . . ? C7 C8 C10 C15 74.4(3) . . . . ? C9 C8 C10 C15 -107.7(3) . . . . ? C7 C8 C10 C16 -47.2(3) . . . . ? C9 C8 C10 C16 130.7(2) . . . . ? C15 C10 C11 C12 72.6(2) . . . . ? C16 C10 C11 C12 -169.26(19) . . . . ? C8 C10 C11 C12 -51.1(3) . . . . ? C9 N1 C12 C11 -29.1(3) . . . . ? C1 N1 C12 C11 158.8(2) . . . . ? C10 C11 C12 N1 59.5(3) . . . . ? C5 C6 C17 C18 -9.2(4) . . . . ? C7 C6 C17 C18 161.3(2) . . . . ? C6 C17 C18 C20 -170.2(3) . . . . ? C22 O1 C19 C20 -3.0(3) . . . . ? C22 O1 C19 C28 -122.8(2) . . . . ? C22 O1 C19 C27 115.2(2) . . . . ? C17 C18 C20 C21 -13.2(5) . . . . ? C17 C18 C20 C19 164.1(2) . . . . ? O1 C19 C20 C21 3.1(3) . . . . ? C28 C19 C20 C21 119.0(2) . . . . ? C27 C19 C20 C21 -111.9(2) . . . . ? O1 C19 C20 C18 -174.7(2) . . . . ? C28 C19 C20 C18 -58.9(3) . . . . ? C27 C19 C20 C18 70.2(3) . . . . ? C18 C20 C21 C22 175.3(3) . . . . ? C19 C20 C21 C22 -2.3(3) . . . . ? C18 C20 C21 C24 -8.9(5) . . . . ? C19 C20 C21 C24 173.5(2) . . . . ? C19 O1 C22 C23 -179.4(2) . . . . ? C19 O1 C22 C21 1.8(3) . . . . ? C20 C21 C22 O1 0.4(3) . . . . ? C24 C21 C22 O1 -175.6(2) . . . . ? C20 C21 C22 C23 -178.3(3) . . . . ? C24 C21 C22 C23 5.8(4) . . . . ? O1 C22 C23 C26 0.6(4) . . . . ? C21 C22 C23 C26 179.1(3) . . . . ? O1 C22 C23 C25 -177.2(2) . . . . ? C21 C22 C23 C25 1.3(4) . . . . ? C20 C21 C24 N2 -21(100) . . . . ? C22 C21 C24 N2 155(100) . . . . ? C22 C23 C25 N3 148(6) . . . . ? C26 C23 C25 N3 -30(6) . . . . ? C22 C23 C26 N4 170(100) . . . . ? C25 C23 C26 N4 -12(14) . . . . ? C7 O2 C29 C30 156.2(2) . . . . ? O2 C29 C30 C35 61.3(3) . . . . ? O2 C29 C30 C31 -118.5(3) . . . . ? C35 C30 C31 C32 -0.2(4) . . . . ? C29 C30 C31 C32 179.6(3) . . . . ? C30 C31 C32 C33 -0.9(4) . . . . ? C31 C32 C33 C34 0.9(5) . . . . ? C32 C33 C34 C35 0.3(4) . . . . ? C31 C30 C35 C34 1.5(4) . . . . ? C29 C30 C35 C34 -178.3(3) . . . . ? C33 C34 C35 C30 -1.5(4) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.253 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.056 # Attachment '- Chromophore B.cif' data_bo1222 _database_code_depnum_ccdc_archive 'CCDC 837248' #TrackingRef '- Chromophore B.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H28 N4 O2' _chemical_formula_weight 464.55 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 13.437(3) _cell_length_b 8.1496(19) _cell_length_c 23.189(6) _cell_angle_alpha 90.00 _cell_angle_beta 96.921(4) _cell_angle_gamma 90.00 _cell_volume 2520.8(11) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 5312 _cell_measurement_theta_min 3.006 _cell_measurement_theta_max 27.475 _exptl_crystal_description Prism _exptl_crystal_colour Blue _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.224 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9659 _exptl_absorpt_correction_T_max 0.9934 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 AFC10/Saturn724+ _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 19462 _diffrn_reflns_av_R_equivalents 0.0684 _diffrn_reflns_av_sigmaI/netI 0.0748 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 27.47 _reflns_number_total 5771 _reflns_number_gt 3400 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0369P)^2^+0.2160P] 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 5771 _refine_ls_number_parameters 320 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1116 _refine_ls_R_factor_gt 0.0552 _refine_ls_wR_factor_ref 0.1090 _refine_ls_wR_factor_gt 0.0942 _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_restrained_S_all 0.998 _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 O1 O 0.28158(9) 0.64557(18) 0.60390(5) 0.0331(3) Uani 1 1 d . . . O2 O 0.36903(9) 0.91580(16) 0.35656(5) 0.0281(3) Uani 1 1 d . . . N1 N 0.52150(11) 0.50486(19) 0.76837(6) 0.0244(4) Uani 1 1 d . . . N2 N 0.71130(12) 0.7785(2) 0.41733(7) 0.0449(5) Uani 1 1 d . . . N3 N 0.67933(13) 0.9751(3) 0.27637(7) 0.0520(6) Uani 1 1 d . . . N4 N 0.36879(13) 1.1001(2) 0.22005(7) 0.0398(5) Uani 1 1 d . . . C1 C 0.01644(15) 0.5754(3) 0.60752(10) 0.0454(6) Uani 1 1 d . . . H1 H 0.0171 0.5047 0.6401 0.054 Uiso 1 1 calc R . . C2 C -0.07251(18) 0.6039(3) 0.57250(14) 0.0681(8) Uani 1 1 d . . . H2 H -0.1326 0.5540 0.5816 0.082 Uiso 1 1 calc R . . C3 C -0.0750(2) 0.7031(4) 0.52492(13) 0.0724(9) Uani 1 1 d . . . H3 H -0.1359 0.7198 0.5003 0.087 Uiso 1 1 calc R . . C4 C 0.0116(2) 0.7784(4) 0.51305(11) 0.0792(10) Uani 1 1 d . . . H4 H 0.0104 0.8489 0.4804 0.095 Uiso 1 1 calc R . . C5 C 0.10087(17) 0.7520(4) 0.54853(10) 0.0607(8) Uani 1 1 d . . . H5 H 0.1603 0.8059 0.5403 0.073 Uiso 1 1 calc R . . C6 C 0.10403(14) 0.6481(3) 0.59573(8) 0.0314(5) Uani 1 1 d . . . C7 C 0.19867(13) 0.6163(3) 0.63569(8) 0.0325(5) Uani 1 1 d . . . H7A H 0.2023 0.6902 0.6698 0.039 Uiso 1 1 calc R . . H7B H 0.1999 0.5015 0.6497 0.039 Uiso 1 1 calc R . . C8 C 0.37615(13) 0.6198(2) 0.63027(8) 0.0248(4) Uani 1 1 d . . . C9 C 0.39789(13) 0.5733(2) 0.68755(8) 0.0246(4) Uani 1 1 d . . . H9 H 0.3451 0.5579 0.7108 0.030 Uiso 1 1 calc R . . C10 C 0.49868(13) 0.5484(2) 0.71199(7) 0.0225(4) Uani 1 1 d . . . C11 C 0.57521(13) 0.5714(2) 0.67552(8) 0.0249(4) Uani 1 1 d . . . H11 H 0.6433 0.5543 0.6906 0.030 Uiso 1 1 calc R . . C12 C 0.55163(13) 0.6179(2) 0.61914(8) 0.0252(4) Uani 1 1 d . . . H12 H 0.6046 0.6326 0.5959 0.030 Uiso 1 1 calc R . . C13 C 0.45233(13) 0.6454(2) 0.59353(7) 0.0227(4) Uani 1 1 d . . . C14 C 0.42555(13) 0.6999(2) 0.53583(8) 0.0250(4) Uani 1 1 d . . . H14 H 0.3565 0.7235 0.5251 0.030 Uiso 1 1 calc R . . C15 C 0.48696(13) 0.7228(2) 0.49350(7) 0.0240(4) Uani 1 1 d . . . H15 H 0.5544 0.6867 0.5016 0.029 Uiso 1 1 calc R . . C16 C 0.35360(13) 0.8526(2) 0.41486(7) 0.0234(4) Uani 1 1 d . . . C17 C 0.45821(13) 0.7957(2) 0.43892(7) 0.0224(4) Uani 1 1 d . . . C18 C 0.52199(13) 0.8327(2) 0.39841(7) 0.0224(4) Uani 1 1 d . . . C19 C 0.46674(13) 0.9095(2) 0.34916(8) 0.0248(4) Uani 1 1 d . . . C20 C 0.44394(14) 0.4787(3) 0.80692(8) 0.0306(5) Uani 1 1 d . . . H20A H 0.4686 0.3983 0.8373 0.037 Uiso 1 1 calc R . . H20B H 0.3835 0.4318 0.7842 0.037 Uiso 1 1 calc R . . C21 C 0.41584(16) 0.6360(3) 0.83551(9) 0.0463(6) Uani 1 1 d . . . H21A H 0.4758 0.6845 0.8572 0.056 Uiso 1 1 calc R . . H21B H 0.3665 0.6122 0.8622 0.056 Uiso 1 1 calc R . . H21C H 0.3870 0.7132 0.8057 0.056 Uiso 1 1 calc R . . C22 C 0.62499(13) 0.4921(2) 0.79642(8) 0.0263(4) Uani 1 1 d . . . H22A H 0.6271 0.5235 0.8378 0.032 Uiso 1 1 calc R . . H22B H 0.6675 0.5703 0.7778 0.032 Uiso 1 1 calc R . . C23 C 0.66755(14) 0.3210(2) 0.79268(9) 0.0351(5) Uani 1 1 d . . . H23A H 0.6245 0.2424 0.8099 0.042 Uiso 1 1 calc R . . H23B H 0.7352 0.3173 0.8139 0.042 Uiso 1 1 calc R . . H23C H 0.6706 0.2926 0.7519 0.042 Uiso 1 1 calc R . . C24 C 0.27621(13) 0.7168(2) 0.40538(8) 0.0278(4) Uani 1 1 d . . . H24A H 0.2131 0.7618 0.3862 0.033 Uiso 1 1 calc R . . H24B H 0.2650 0.6696 0.4429 0.033 Uiso 1 1 calc R . . H24C H 0.3005 0.6312 0.3809 0.033 Uiso 1 1 calc R . . C25 C 0.31741(14) 0.9988(2) 0.44729(8) 0.0315(5) Uani 1 1 d . . . H25A H 0.3696 1.0834 0.4515 0.038 Uiso 1 1 calc R . . H25B H 0.3028 0.9637 0.4858 0.038 Uiso 1 1 calc R . . H25C H 0.2565 1.0436 0.4254 0.038 Uiso 1 1 calc R . . C26 C 0.62718(15) 0.8040(2) 0.40665(8) 0.0287(5) Uani 1 1 d . . . C27 C 0.49654(13) 0.9735(2) 0.29919(8) 0.0252(4) Uani 1 1 d . . . C28 C 0.59842(15) 0.9722(3) 0.28789(8) 0.0327(5) Uani 1 1 d . . . C29 C 0.42530(14) 1.0451(2) 0.25581(8) 0.0284(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 O1 0.0182(7) 0.0576(10) 0.0239(7) 0.0075(7) 0.0032(5) 0.0027(6) O2 0.0245(7) 0.0396(8) 0.0201(7) 0.0062(6) 0.0026(5) 0.0018(6) N1 0.0234(8) 0.0323(10) 0.0172(8) 0.0011(7) 0.0010(6) 0.0003(7) N2 0.0286(10) 0.0716(14) 0.0345(10) 0.0095(10) 0.0033(8) 0.0037(10) N3 0.0377(12) 0.0871(17) 0.0332(11) 0.0105(11) 0.0117(9) 0.0027(11) N4 0.0520(12) 0.0377(11) 0.0278(10) 0.0040(8) -0.0022(9) 0.0072(9) C1 0.0284(12) 0.0393(14) 0.0669(16) -0.0032(12) -0.0006(11) -0.0038(10) C2 0.0308(14) 0.0618(19) 0.107(2) -0.0221(17) -0.0129(15) -0.0059(13) C3 0.0413(17) 0.102(3) 0.067(2) -0.0313(18) -0.0236(14) 0.0276(16) C4 0.0530(18) 0.140(3) 0.0420(16) 0.0187(17) -0.0037(13) 0.0385(19) C5 0.0352(13) 0.108(2) 0.0394(14) 0.0215(15) 0.0057(11) 0.0146(14) C6 0.0230(11) 0.0432(13) 0.0274(11) -0.0093(9) 0.0012(8) 0.0059(9) C7 0.0247(11) 0.0493(14) 0.0248(10) 0.0007(10) 0.0084(8) 0.0028(10) C8 0.0222(10) 0.0286(11) 0.0232(10) 0.0004(8) 0.0008(8) 0.0013(8) C9 0.0224(10) 0.0312(11) 0.0211(9) 0.0016(8) 0.0060(8) -0.0012(8) C10 0.0255(10) 0.0225(10) 0.0188(9) -0.0011(8) 0.0006(8) -0.0015(8) C11 0.0223(10) 0.0268(11) 0.0248(10) -0.0006(8) -0.0003(8) -0.0007(8) C12 0.0257(10) 0.0285(11) 0.0222(10) 0.0003(8) 0.0063(8) -0.0023(8) C13 0.0215(10) 0.0272(10) 0.0189(9) 0.0001(8) 0.0010(8) -0.0018(8) C14 0.0229(10) 0.0282(11) 0.0230(10) -0.0012(8) -0.0005(8) -0.0033(8) C15 0.0221(10) 0.0289(11) 0.0202(9) -0.0004(8) -0.0005(7) -0.0008(8) C16 0.0228(10) 0.0307(11) 0.0164(9) 0.0021(8) 0.0015(7) -0.0014(8) C17 0.0228(10) 0.0247(10) 0.0190(9) -0.0035(8) 0.0004(8) -0.0032(8) C18 0.0207(10) 0.0279(10) 0.0182(9) -0.0012(8) 0.0010(7) -0.0032(8) C19 0.0231(10) 0.0260(11) 0.0247(10) -0.0022(8) 0.0009(8) -0.0017(8) C20 0.0292(11) 0.0417(13) 0.0208(10) 0.0058(9) 0.0031(8) -0.0023(10) C21 0.0435(14) 0.0666(17) 0.0304(12) -0.0063(12) 0.0109(10) 0.0066(12) C22 0.0259(10) 0.0315(11) 0.0200(10) 0.0019(8) -0.0037(8) -0.0017(9) C23 0.0315(12) 0.0324(12) 0.0407(13) 0.0007(10) 0.0013(9) 0.0009(9) C24 0.0245(10) 0.0343(12) 0.0241(10) -0.0028(9) 0.0007(8) -0.0021(9) C25 0.0333(12) 0.0318(12) 0.0294(11) -0.0011(9) 0.0044(9) 0.0008(9) C26 0.0268(11) 0.0407(13) 0.0189(10) 0.0046(9) 0.0042(8) -0.0036(10) C27 0.0269(11) 0.0298(11) 0.0188(9) 0.0001(8) 0.0024(8) -0.0010(9) C28 0.0362(13) 0.0429(13) 0.0194(10) 0.0068(9) 0.0044(9) -0.0001(10) C29 0.0350(12) 0.0271(11) 0.0238(10) -0.0015(9) 0.0061(9) -0.0014(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 O1 C8 1.358(2) . ? O1 C7 1.428(2) . ? O2 C19 1.345(2) . ? O2 C16 1.484(2) . ? N1 C10 1.354(2) . ? N1 C22 1.466(2) . ? N1 C20 1.468(2) . ? N2 C26 1.147(2) . ? N3 C28 1.151(2) . ? N4 C29 1.146(2) . ? C1 C6 1.374(3) . ? C1 C2 1.381(3) . ? C1 H1 0.9500 . ? C2 C3 1.365(4) . ? C2 H2 0.9500 . ? C3 C4 1.372(4) . ? C3 H3 0.9500 . ? C4 C5 1.387(3) . ? C4 H4 0.9500 . ? C5 C6 1.381(3) . ? C5 H5 0.9500 . ? C6 C7 1.503(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.378(2) . ? C8 C13 1.424(2) . ? C9 C10 1.418(2) . ? C9 H9 0.9500 . ? C10 C11 1.420(2) . ? C11 C12 1.361(2) . ? C11 H11 0.9500 . ? C12 C13 1.411(2) . ? C12 H12 0.9500 . ? C13 C14 1.415(2) . ? C14 C15 1.369(2) . ? C14 H14 0.9500 . ? C15 C17 1.409(2) . ? C15 H15 0.9500 . ? C16 C24 1.516(2) . ? C16 C25 1.519(2) . ? C16 C17 1.521(2) . ? C17 C18 1.379(2) . ? C18 C26 1.423(3) . ? C18 C19 1.429(2) . ? C19 C27 1.374(2) . ? C20 C21 1.512(3) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 C23 1.513(3) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C27 C28 1.424(3) . ? C27 C29 1.427(3) . ? 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 O1 C7 119.17(14) . . ? C19 O2 C16 110.39(13) . . ? C10 N1 C22 122.64(14) . . ? C10 N1 C20 122.10(15) . . ? C22 N1 C20 115.12(14) . . ? C6 C1 C2 120.8(2) . . ? C6 C1 H1 119.6 . . ? C2 C1 H1 119.6 . . ? C3 C2 C1 120.7(3) . . ? C3 C2 H2 119.7 . . ? C1 C2 H2 119.7 . . ? C2 C3 C4 119.2(2) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C3 C4 C5 120.4(3) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C6 C5 C4 120.5(2) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C1 C6 C5 118.5(2) . . ? C1 C6 C7 118.97(19) . . ? C5 C6 C7 122.51(19) . . ? O1 C7 C6 107.92(15) . . ? O1 C7 H7A 110.1 . . ? C6 C7 H7A 110.1 . . ? O1 C7 H7B 110.1 . . ? C6 C7 H7B 110.1 . . ? H7A C7 H7B 108.4 . . ? O1 C8 C9 123.68(16) . . ? O1 C8 C13 114.13(15) . . ? C9 C8 C13 122.19(16) . . ? C8 C9 C10 120.38(16) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? N1 C10 C9 121.17(16) . . ? N1 C10 C11 120.91(16) . . ? C9 C10 C11 117.92(16) . . ? C12 C11 C10 120.48(17) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C11 C12 C13 123.16(17) . . ? C11 C12 H12 118.4 . . ? C13 C12 H12 118.4 . . ? C12 C13 C14 124.58(16) . . ? C12 C13 C8 115.87(16) . . ? C14 C13 C8 119.53(16) . . ? C15 C14 C13 127.91(17) . . ? C15 C14 H14 116.0 . . ? C13 C14 H14 116.0 . . ? C14 C15 C17 125.29(17) . . ? C14 C15 H15 117.4 . . ? C17 C15 H15 117.4 . . ? O2 C16 C24 106.84(14) . . ? O2 C16 C25 105.49(14) . . ? C24 C16 C25 112.91(15) . . ? O2 C16 C17 102.45(13) . . ? C24 C16 C17 114.69(16) . . ? C25 C16 C17 113.22(15) . . ? C18 C17 C15 125.34(17) . . ? C18 C17 C16 107.82(15) . . ? C15 C17 C16 126.81(15) . . ? C17 C18 C26 124.16(17) . . ? C17 C18 C19 109.55(16) . . ? C26 C18 C19 126.24(16) . . ? O2 C19 C27 118.76(16) . . ? O2 C19 C18 109.62(15) . . ? C27 C19 C18 131.62(17) . . ? N1 C20 C21 112.14(16) . . ? N1 C20 H20A 109.2 . . ? C21 C20 H20A 109.2 . . ? N1 C20 H20B 109.2 . . ? C21 C20 H20B 109.2 . . ? H20A C20 H20B 107.9 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N1 C22 C23 112.64(15) . . ? N1 C22 H22A 109.1 . . ? C23 C22 H22A 109.1 . . ? N1 C22 H22B 109.1 . . ? C23 C22 H22B 109.1 . . ? H22A C22 H22B 107.8 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C16 C24 H24A 109.5 . . ? C16 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C16 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C16 C25 H25A 109.5 . . ? C16 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C16 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? N2 C26 C18 175.14(19) . . ? C19 C27 C28 122.45(17) . . ? C19 C27 C29 120.73(16) . . ? C28 C27 C29 116.82(16) . . ? N3 C28 C27 176.8(2) . . ? N4 C29 C27 178.4(2) . . ? 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 C6 C1 C2 C3 1.0(4) . . . . ? C1 C2 C3 C4 -1.9(4) . . . . ? C2 C3 C4 C5 1.0(4) . . . . ? C3 C4 C5 C6 0.9(4) . . . . ? C2 C1 C6 C5 0.9(3) . . . . ? C2 C1 C6 C7 178.8(2) . . . . ? C4 C5 C6 C1 -1.8(4) . . . . ? C4 C5 C6 C7 -179.6(2) . . . . ? C8 O1 C7 C6 -177.87(16) . . . . ? C1 C6 C7 O1 156.91(18) . . . . ? C5 C6 C7 O1 -25.3(3) . . . . ? C7 O1 C8 C9 -3.0(3) . . . . ? C7 O1 C8 C13 177.16(16) . . . . ? O1 C8 C9 C10 179.90(17) . . . . ? C13 C8 C9 C10 -0.3(3) . . . . ? C22 N1 C10 C9 -174.54(16) . . . . ? C20 N1 C10 C9 0.9(3) . . . . ? C22 N1 C10 C11 5.2(3) . . . . ? C20 N1 C10 C11 -179.39(17) . . . . ? C8 C9 C10 N1 179.15(17) . . . . ? C8 C9 C10 C11 -0.6(3) . . . . ? N1 C10 C11 C12 -178.90(17) . . . . ? C9 C10 C11 C12 0.8(3) . . . . ? C10 C11 C12 C13 -0.2(3) . . . . ? C11 C12 C13 C14 177.41(18) . . . . ? C11 C12 C13 C8 -0.7(3) . . . . ? O1 C8 C13 C12 -179.27(16) . . . . ? C9 C8 C13 C12 0.9(3) . . . . ? O1 C8 C13 C14 2.5(3) . . . . ? C9 C8 C13 C14 -177.27(18) . . . . ? C12 C13 C14 C15 5.7(3) . . . . ? C8 C13 C14 C15 -176.22(18) . . . . ? C13 C14 C15 C17 -172.07(18) . . . . ? C19 O2 C16 C24 -125.05(15) . . . . ? C19 O2 C16 C25 114.57(15) . . . . ? C19 O2 C16 C17 -4.13(18) . . . . ? C14 C15 C17 C18 173.62(18) . . . . ? C14 C15 C17 C16 -4.1(3) . . . . ? O2 C16 C17 C18 2.54(18) . . . . ? C24 C16 C17 C18 117.89(17) . . . . ? C25 C16 C17 C18 -110.55(17) . . . . ? O2 C16 C17 C15 -179.38(17) . . . . ? C24 C16 C17 C15 -64.0(2) . . . . ? C25 C16 C17 C15 67.5(2) . . . . ? C15 C17 C18 C26 -0.9(3) . . . . ? C16 C17 C18 C26 177.20(17) . . . . ? C15 C17 C18 C19 -178.36(17) . . . . ? C16 C17 C18 C19 -0.2(2) . . . . ? C16 O2 C19 C27 -175.58(16) . . . . ? C16 O2 C19 C18 4.2(2) . . . . ? C17 C18 C19 O2 -2.5(2) . . . . ? C26 C18 C19 O2 -179.86(17) . . . . ? C17 C18 C19 C27 177.3(2) . . . . ? C26 C18 C19 C27 -0.1(3) . . . . ? C10 N1 C20 C21 -87.2(2) . . . . ? C22 N1 C20 C21 88.60(19) . . . . ? C10 N1 C22 C23 -91.6(2) . . . . ? C20 N1 C22 C23 92.64(19) . . . . ? C17 C18 C26 N2 -10(3) . . . . ? C19 C18 C26 N2 167(3) . . . . ? O2 C19 C27 C28 179.86(17) . . . . ? C18 C19 C27 C28 0.1(3) . . . . ? O2 C19 C27 C29 -0.1(3) . . . . ? C18 C19 C27 C29 -179.88(19) . . . . ? C19 C27 C28 N3 -178(100) . . . . ? C29 C27 C28 N3 2(4) . . . . ? C19 C27 C29 N4 -123(8) . . . . ? C28 C27 C29 N4 57(8) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.205 _refine_diff_density_min -0.181 _refine_diff_density_rms 0.044