# Supplementary Material (ESI) for Chemical Communications # This journal is (c) 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 'Bin Liu' _publ_contact_author_email CHELIUB@NUS.EDU.SG _publ_section_title ; Bridged Triphenylamine Based Molecules with Large Two-Photon Absorption Cross Sections in Organic and Aqueous Media ; loop_ _publ_author_name 'Bin Liu.' 'Zhen Fang.' 'Yee-Hing Lai.' 'Xinhai Zhang.' # Attachment '6378-2.cif' data_6378 _database_code_depnum_ccdc_archive 'CCDC 711074' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H27 N' _chemical_formula_weight 365.50 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' _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 9.8160(5) _cell_length_b 18.6778(9) _cell_length_c 21.7184(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.0680(10) _cell_angle_gamma 90.00 _cell_volume 3981.9(3) _cell_formula_units_Z 8 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 2548 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 22.23 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 1.219 _exptl_crystal_density_diffrn 1.219 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1568 _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9835 _exptl_absorpt_correction_T_max 0.9944 _exptl_absorpt_process_details 'Semi-empirical from equivalents' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22962 _diffrn_reflns_av_R_equivalents 0.0555 _diffrn_reflns_av_sigmaI/netI 0.0535 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.44 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7020 _reflns_number_gt 5329 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0761P)^2^+16.1873P] 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 7020 _refine_ls_number_parameters 517 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1472 _refine_ls_R_factor_gt 0.1234 _refine_ls_wR_factor_ref 0.3063 _refine_ls_wR_factor_gt 0.2945 _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_restrained_S_all 1.105 _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 0.7348(4) 0.7484(2) 0.23866(18) 0.0343(10) Uani 1 1 d . . . N2 N 0.2356(4) 0.7584(2) 0.00774(18) 0.0309(9) Uani 1 1 d . . . C1 C 0.7401(5) 0.8253(3) 0.2460(2) 0.0344(11) Uani 1 1 d . . . C2 C 0.6596(5) 0.8694(3) 0.2075(2) 0.0401(12) Uani 1 1 d . . . C3 C 0.6729(7) 0.9424(3) 0.2118(3) 0.0555(16) Uani 1 1 d . . . H3 H 0.6203 0.9719 0.1860 0.067 Uiso 1 1 calc R . . C4 C 0.7601(8) 0.9731(3) 0.2526(3) 0.0654(19) Uani 1 1 d . . . H4 H 0.7722 1.0230 0.2532 0.079 Uiso 1 1 calc R . . C5 C 0.8304(7) 0.9302(3) 0.2928(3) 0.0555(16) Uani 1 1 d . . . H5 H 0.8850 0.9515 0.3233 0.067 Uiso 1 1 calc R . . C6 C 0.8228(5) 0.8565(3) 0.2897(2) 0.0370(12) Uani 1 1 d . . . C7 C 0.9014(6) 0.8142(3) 0.3378(2) 0.0419(13) Uani 1 1 d . . . C8 C 0.8918(5) 0.7350(3) 0.3255(2) 0.0390(12) Uani 1 1 d . . . C9 C 0.9614(7) 0.6881(4) 0.3633(3) 0.0584(17) Uani 1 1 d . . . H9 H 1.0120 0.7075 0.3961 0.070 Uiso 1 1 calc R . . C10 C 0.9617(9) 0.6152(4) 0.3562(4) 0.080(2) Uani 1 1 d . . . H10 H 1.0063 0.5851 0.3845 0.097 Uiso 1 1 calc R . . C11 C 0.8935(8) 0.5877(3) 0.3057(4) 0.0665(19) Uani 1 1 d . . . H11 H 0.8952 0.5380 0.2987 0.080 Uiso 1 1 calc R . . C12 C 0.8235(6) 0.6307(3) 0.2655(3) 0.0515(15) Uani 1 1 d . . . C13 C 0.8164(5) 0.7047(3) 0.2761(2) 0.0366(12) Uani 1 1 d . . . C14 C 0.7516(6) 0.5964(3) 0.2111(3) 0.0542(16) Uani 1 1 d . . . C15 C 0.7190(6) 0.6523(3) 0.1620(3) 0.0512(16) Uani 1 1 d . . . C16 C 0.6950(8) 0.6333(5) 0.1011(4) 0.081(2) Uani 1 1 d . . . H16 H 0.7180 0.5869 0.0879 0.097 Uiso 1 1 calc R . . C17 C 0.6388(9) 0.6800(5) 0.0598(3) 0.080(3) Uani 1 1 d . . . H17 H 0.6316 0.6677 0.0180 0.096 Uiso 1 1 calc R . . C18 C 0.5929(7) 0.7456(4) 0.0805(3) 0.0652(19) Uani 1 1 d . . . H18 H 0.5440 0.7755 0.0536 0.078 Uiso 1 1 calc R . . C19 C 0.6175(6) 0.7680(3) 0.1403(2) 0.0480(15) Uani 1 1 d . . . C20 C 0.6912(5) 0.7230(3) 0.1799(2) 0.0414(13) Uani 1 1 d . . . C21 C 0.5547(6) 0.8355(3) 0.1658(3) 0.0490(15) Uani 1 1 d . . . C22 C 0.8449(7) 0.8310(4) 0.4014(3) 0.0607(17) Uani 1 1 d . . . H22A H 0.7497 0.8172 0.4032 0.091 Uiso 1 1 calc R . . H22B H 0.8532 0.8819 0.4094 0.091 Uiso 1 1 calc R . . H22C H 0.8958 0.8046 0.4322 0.091 Uiso 1 1 calc R . . C23 C 1.0544(6) 0.8352(4) 0.3360(3) 0.0573(17) Uani 1 1 d . . . H23A H 1.1023 0.8112 0.3693 0.086 Uiso 1 1 calc R . . H23B H 1.0633 0.8866 0.3408 0.086 Uiso 1 1 calc R . . H23C H 1.0933 0.8207 0.2969 0.086 Uiso 1 1 calc R . . C24 C 0.8404(9) 0.5353(5) 0.1843(4) 0.098(3) Uani 1 1 d . . . H24A H 0.9256 0.5549 0.1694 0.147 Uiso 1 1 calc R . . H24B H 0.7922 0.5125 0.1506 0.147 Uiso 1 1 calc R . . H24C H 0.8588 0.5003 0.2162 0.147 Uiso 1 1 calc R . . C25 C 0.6146(8) 0.5649(4) 0.2341(4) 0.081(2) Uani 1 1 d . . . H25A H 0.6321 0.5302 0.2664 0.122 Uiso 1 1 calc R . . H25B H 0.5679 0.5417 0.2002 0.122 Uiso 1 1 calc R . . H25C H 0.5581 0.6032 0.2502 0.122 Uiso 1 1 calc R . . C26 C 0.4311(6) 0.8122(4) 0.2055(3) 0.071(2) Uani 1 1 d . . . H26A H 0.3698 0.7833 0.1808 0.106 Uiso 1 1 calc R . . H26B H 0.3834 0.8544 0.2201 0.106 Uiso 1 1 calc R . . H26C H 0.4629 0.7844 0.2404 0.106 Uiso 1 1 calc R . . C27 C 0.5016(8) 0.8870(4) 0.1159(3) 0.079(2) Uani 1 1 d . . . H27A H 0.5780 0.9064 0.0930 0.118 Uiso 1 1 calc R . . H27B H 0.4517 0.9258 0.1352 0.118 Uiso 1 1 calc R . . H27C H 0.4417 0.8613 0.0880 0.118 Uiso 1 1 calc R . . C28 C 0.2430(5) 0.8340(3) -0.0009(2) 0.0360(12) Uani 1 1 d . . . C29 C 0.3290(6) 0.8649(3) -0.0443(2) 0.0404(13) Uani 1 1 d . . . C30 C 0.3434(7) 0.9375(3) -0.0461(3) 0.0569(17) Uani 1 1 d . . . H30 H 0.4039 0.9581 -0.0746 0.068 Uiso 1 1 calc R . . C31 C 0.2697(8) 0.9817(3) -0.0065(3) 0.069(2) Uani 1 1 d . . . H31 H 0.2822 1.0316 -0.0074 0.083 Uiso 1 1 calc R . . C32 C 0.1797(7) 0.9519(3) 0.0334(3) 0.0579(17) Uani 1 1 d . . . H32 H 0.1268 0.9818 0.0586 0.070 Uiso 1 1 calc R . . C33 C 0.1639(5) 0.8785(3) 0.0378(3) 0.0410(13) Uani 1 1 d . . . C34 C 0.0540(6) 0.8453(3) 0.0775(3) 0.0470(14) Uani 1 1 d . . . C35 C 0.1122(5) 0.7765(3) 0.1039(2) 0.0433(13) Uani 1 1 d . . . C36 C 0.0836(6) 0.7539(4) 0.1635(3) 0.0549(16) Uani 1 1 d . . . H36 H 0.0372 0.7847 0.1905 0.066 Uiso 1 1 calc R . . C37 C 0.1223(8) 0.6874(4) 0.1832(3) 0.069(2) Uani 1 1 d . . . H37 H 0.1085 0.6737 0.2244 0.083 Uiso 1 1 calc R . . C38 C 0.1822(7) 0.6404(4) 0.1418(3) 0.0639(18) Uani 1 1 d . . . H38 H 0.2035 0.5938 0.1548 0.077 Uiso 1 1 calc R . . C39 C 0.2115(5) 0.6607(3) 0.0815(3) 0.0440(13) Uani 1 1 d . . . C40 C 0.1876(5) 0.7316(3) 0.0651(2) 0.0376(12) Uani 1 1 d . . . C41 C 0.2521(6) 0.6049(3) 0.0342(3) 0.0501(15) Uani 1 1 d . . . C42 C 0.3199(5) 0.6393(3) -0.0208(3) 0.0389(12) Uani 1 1 d . . . C43 C 0.3863(7) 0.5957(3) -0.0626(3) 0.0590(17) Uani 1 1 d . . . H43 H 0.3838 0.5458 -0.0566 0.071 Uiso 1 1 calc R . . C44 C 0.4553(7) 0.6220(4) -0.1123(3) 0.0634(18) Uani 1 1 d . . . H44 H 0.4985 0.5914 -0.1406 0.076 Uiso 1 1 calc R . . C45 C 0.4589(7) 0.6951(3) -0.1191(3) 0.0550(16) Uani 1 1 d . . . H45 H 0.5093 0.7145 -0.1519 0.066 Uiso 1 1 calc R . . C46 C 0.3916(5) 0.7417(3) -0.0799(2) 0.0381(12) Uani 1 1 d . . . C47 C 0.3155(5) 0.7129(3) -0.0311(2) 0.0355(12) Uani 1 1 d . . . C48 C 0.4078(6) 0.8212(3) -0.0921(2) 0.0425(13) Uani 1 1 d . . . C49 C 0.0058(8) 0.8969(4) 0.1287(3) 0.075(2) Uani 1 1 d . . . H49A H -0.0688 0.8751 0.1512 0.112 Uiso 1 1 calc R . . H49B H -0.0247 0.9414 0.1103 0.112 Uiso 1 1 calc R . . H49C H 0.0807 0.9064 0.1567 0.112 Uiso 1 1 calc R . . C50 C -0.0695(6) 0.8256(4) 0.0377(3) 0.0663(19) Uani 1 1 d . . . H50A H -0.0422 0.7913 0.0066 0.099 Uiso 1 1 calc R . . H50B H -0.1048 0.8683 0.0180 0.099 Uiso 1 1 calc R . . H50C H -0.1396 0.8046 0.0635 0.099 Uiso 1 1 calc R . . C51 C 0.1176(7) 0.5686(4) 0.0138(4) 0.075(2) Uani 1 1 d . . . H51A H 0.0560 0.6045 -0.0026 0.113 Uiso 1 1 calc R . . H51B H 0.0756 0.5454 0.0489 0.113 Uiso 1 1 calc R . . H51C H 0.1368 0.5333 -0.0178 0.113 Uiso 1 1 calc R . . C52 C 0.3436(9) 0.5469(4) 0.0628(4) 0.086(3) Uani 1 1 d . . . H52A H 0.3596 0.5094 0.0328 0.128 Uiso 1 1 calc R . . H52B H 0.2990 0.5268 0.0987 0.128 Uiso 1 1 calc R . . H52C H 0.4299 0.5680 0.0749 0.128 Uiso 1 1 calc R . . C53 C 0.5605(6) 0.8410(4) -0.0889(3) 0.0597(17) Uani 1 1 d . . . H53A H 0.5970 0.8272 -0.0491 0.090 Uiso 1 1 calc R . . H53B H 0.5709 0.8922 -0.0944 0.090 Uiso 1 1 calc R . . H53C H 0.6094 0.8160 -0.1211 0.090 Uiso 1 1 calc R . . C54 C 0.3493(8) 0.8401(4) -0.1557(3) 0.0654(19) Uani 1 1 d . . . H54A H 0.3979 0.8136 -0.1872 0.098 Uiso 1 1 calc R . . H54B H 0.3596 0.8910 -0.1629 0.098 Uiso 1 1 calc R . . H54C H 0.2534 0.8275 -0.1570 0.098 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 0.034(2) 0.035(2) 0.034(2) -0.0001(18) -0.0019(18) -0.0098(19) N2 0.033(2) 0.029(2) 0.031(2) 0.0031(17) 0.0024(17) -0.0017(17) C1 0.031(3) 0.040(3) 0.033(3) 0.002(2) 0.008(2) 0.001(2) C2 0.041(3) 0.044(3) 0.036(3) 0.005(2) -0.001(2) -0.003(2) C3 0.062(4) 0.045(4) 0.060(4) 0.007(3) -0.015(3) 0.013(3) C4 0.089(5) 0.034(3) 0.073(5) -0.002(3) -0.023(4) 0.008(3) C5 0.064(4) 0.048(4) 0.054(4) -0.015(3) -0.012(3) 0.000(3) C6 0.036(3) 0.036(3) 0.039(3) -0.007(2) 0.000(2) -0.001(2) C7 0.047(3) 0.045(3) 0.034(3) -0.002(2) -0.003(2) -0.002(3) C8 0.042(3) 0.039(3) 0.036(3) 0.007(2) -0.002(2) -0.003(2) C9 0.065(4) 0.057(4) 0.053(4) 0.013(3) -0.005(3) 0.003(3) C10 0.105(6) 0.049(4) 0.087(6) 0.030(4) -0.006(5) 0.016(4) C11 0.080(5) 0.036(3) 0.083(5) 0.010(3) -0.001(4) 0.002(3) C12 0.047(3) 0.031(3) 0.077(4) 0.005(3) 0.011(3) -0.006(3) C13 0.039(3) 0.034(3) 0.038(3) 0.002(2) 0.009(2) -0.003(2) C14 0.049(3) 0.037(3) 0.077(4) -0.017(3) 0.005(3) -0.012(3) C15 0.048(3) 0.060(4) 0.046(3) -0.016(3) 0.012(3) -0.020(3) C16 0.093(6) 0.082(6) 0.067(5) -0.040(4) 0.012(4) -0.030(5) C17 0.097(6) 0.106(7) 0.037(4) -0.013(4) -0.003(4) -0.040(5) C18 0.066(4) 0.084(5) 0.046(4) -0.004(4) -0.014(3) -0.032(4) C19 0.047(3) 0.063(4) 0.034(3) 0.002(3) -0.005(2) -0.028(3) C20 0.039(3) 0.054(3) 0.031(3) -0.004(2) 0.007(2) -0.019(3) C21 0.044(3) 0.060(4) 0.042(3) 0.013(3) -0.008(3) -0.010(3) C22 0.081(5) 0.061(4) 0.039(3) -0.005(3) -0.008(3) 0.006(4) C23 0.054(4) 0.060(4) 0.058(4) 0.005(3) -0.015(3) -0.019(3) C24 0.099(7) 0.081(6) 0.113(7) -0.042(5) 0.001(5) 0.014(5) C25 0.074(5) 0.068(5) 0.101(6) 0.009(4) 0.001(4) -0.029(4) C26 0.040(3) 0.099(6) 0.073(5) 0.017(4) -0.004(3) -0.008(4) C27 0.082(5) 0.086(5) 0.068(5) 0.025(4) -0.033(4) -0.017(4) C28 0.042(3) 0.033(3) 0.034(3) -0.002(2) -0.004(2) 0.004(2) C29 0.042(3) 0.036(3) 0.043(3) 0.010(2) 0.003(2) 0.002(2) C30 0.075(4) 0.041(3) 0.055(4) 0.008(3) 0.016(3) -0.005(3) C31 0.092(5) 0.035(3) 0.081(5) 0.004(3) 0.021(4) 0.003(3) C32 0.068(4) 0.040(4) 0.065(4) -0.007(3) 0.014(3) 0.010(3) C33 0.039(3) 0.038(3) 0.045(3) -0.001(2) 0.006(2) 0.011(2) C34 0.043(3) 0.052(4) 0.047(3) -0.017(3) 0.008(3) 0.002(3) C35 0.038(3) 0.054(3) 0.038(3) -0.006(3) 0.004(2) -0.015(3) C36 0.056(4) 0.064(4) 0.044(3) -0.001(3) 0.011(3) -0.016(3) C37 0.079(5) 0.088(6) 0.041(4) 0.016(4) 0.016(3) -0.028(4) C38 0.070(4) 0.059(4) 0.063(4) 0.023(3) 0.001(4) -0.014(3) C39 0.038(3) 0.043(3) 0.051(3) 0.009(3) -0.005(2) -0.012(2) C40 0.032(3) 0.044(3) 0.037(3) 0.001(2) -0.002(2) -0.009(2) C41 0.046(3) 0.038(3) 0.067(4) 0.006(3) -0.004(3) 0.000(3) C42 0.034(3) 0.030(3) 0.052(3) -0.004(2) -0.004(2) 0.003(2) C43 0.061(4) 0.038(3) 0.078(5) -0.007(3) -0.004(3) 0.009(3) C44 0.077(5) 0.051(4) 0.062(4) -0.017(3) 0.011(4) 0.015(3) C45 0.063(4) 0.056(4) 0.046(3) -0.007(3) 0.016(3) 0.008(3) C46 0.037(3) 0.048(3) 0.029(3) 0.002(2) 0.001(2) 0.003(2) C47 0.034(3) 0.038(3) 0.034(3) -0.004(2) -0.005(2) 0.004(2) C48 0.048(3) 0.045(3) 0.035(3) 0.001(2) 0.004(2) 0.000(3) C49 0.085(5) 0.069(5) 0.070(5) -0.019(4) 0.040(4) -0.001(4) C50 0.040(3) 0.084(5) 0.075(5) -0.002(4) -0.001(3) 0.001(3) C51 0.064(4) 0.061(5) 0.100(6) -0.014(4) 0.007(4) -0.028(4) C52 0.091(6) 0.069(5) 0.097(6) 0.042(5) 0.003(5) 0.023(4) C53 0.058(4) 0.057(4) 0.064(4) 0.005(3) 0.018(3) -0.006(3) C54 0.092(5) 0.065(4) 0.040(3) 0.008(3) 0.004(3) 0.016(4) _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 C13 1.402(7) . ? N1 C20 1.426(6) . ? N1 C1 1.447(7) . ? N2 C40 1.424(6) . ? N2 C28 1.426(6) . ? N2 C47 1.432(6) . ? C1 C6 1.377(7) . ? C1 C2 1.414(7) . ? C2 C3 1.374(8) . ? C2 C21 1.510(8) . ? C3 C4 1.357(9) . ? C3 H3 0.9400 . ? C4 C5 1.372(9) . ? C4 H4 0.9400 . ? C5 C6 1.382(8) . ? C5 H5 0.9400 . ? C6 C7 1.519(7) . ? C7 C8 1.507(8) . ? C7 C22 1.522(8) . ? C7 C23 1.552(8) . ? C8 C9 1.381(8) . ? C8 C13 1.421(7) . ? C9 C10 1.371(10) . ? C9 H9 0.9400 . ? C10 C11 1.383(10) . ? C10 H10 0.9400 . ? C11 C12 1.370(9) . ? C11 H11 0.9400 . ? C12 C13 1.403(7) . ? C12 C14 1.518(9) . ? C14 C15 1.526(9) . ? C14 C24 1.549(9) . ? C14 C25 1.550(9) . ? C15 C16 1.390(9) . ? C15 C20 1.404(8) . ? C16 C17 1.367(11) . ? C16 H16 0.9400 . ? C17 C18 1.380(11) . ? C17 H17 0.9400 . ? C18 C19 1.385(8) . ? C18 H18 0.9400 . ? C19 C20 1.403(8) . ? C19 C21 1.508(9) . ? C21 C27 1.540(8) . ? C21 C26 1.551(8) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C22 H22C 0.9700 . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C23 H23C 0.9700 . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C24 H24C 0.9700 . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C25 H25C 0.9700 . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C26 H26C 0.9700 . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C27 H27C 0.9700 . ? C28 C29 1.391(7) . ? C28 C33 1.414(7) . ? C29 C30 1.363(8) . ? C29 C48 1.531(8) . ? C30 C31 1.397(9) . ? C30 H30 0.9400 . ? C31 C32 1.357(9) . ? C31 H31 0.9400 . ? C32 C33 1.381(8) . ? C32 H32 0.9400 . ? C33 C34 1.515(8) . ? C34 C35 1.519(8) . ? C34 C50 1.532(8) . ? C34 C49 1.546(8) . ? C35 C36 1.389(8) . ? C35 C40 1.401(8) . ? C36 C37 1.368(10) . ? C36 H36 0.9400 . ? C37 C38 1.387(10) . ? C37 H37 0.9400 . ? C38 C39 1.393(8) . ? C38 H38 0.9400 . ? C39 C40 1.392(8) . ? C39 C41 1.517(8) . ? C41 C42 1.512(8) . ? C41 C52 1.536(8) . ? C41 C51 1.549(9) . ? C42 C43 1.384(8) . ? C42 C47 1.393(7) . ? C43 C44 1.366(9) . ? C43 H43 0.9400 . ? C44 C45 1.375(9) . ? C44 H44 0.9400 . ? C45 C46 1.385(8) . ? C45 H45 0.9400 . ? C46 C47 1.405(7) . ? C46 C48 1.516(8) . ? C48 C54 1.536(8) . ? C48 C53 1.546(8) . ? C49 H49A 0.9700 . ? C49 H49B 0.9700 . ? C49 H49C 0.9700 . ? C50 H50A 0.9700 . ? C50 H50B 0.9700 . ? C50 H50C 0.9700 . ? C51 H51A 0.9700 . ? C51 H51B 0.9700 . ? C51 H51C 0.9700 . ? C52 H52A 0.9700 . ? C52 H52B 0.9700 . ? C52 H52C 0.9700 . ? C53 H53A 0.9700 . ? C53 H53B 0.9700 . ? C53 H53C 0.9700 . ? C54 H54A 0.9700 . ? C54 H54B 0.9700 . ? C54 H54C 0.9700 . ? 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 C13 N1 C20 119.8(4) . . ? C13 N1 C1 119.6(4) . . ? C20 N1 C1 116.0(4) . . ? C40 N2 C28 118.7(4) . . ? C40 N2 C47 119.3(4) . . ? C28 N2 C47 118.9(4) . . ? C6 C1 C2 119.3(5) . . ? C6 C1 N1 121.1(5) . . ? C2 C1 N1 119.6(5) . . ? C3 C2 C1 119.0(5) . . ? C3 C2 C21 121.5(5) . . ? C1 C2 C21 119.4(5) . . ? C4 C3 C2 121.6(6) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C3 C4 C5 119.1(6) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? C4 C5 C6 121.5(6) . . ? C4 C5 H5 119.2 . . ? C6 C5 H5 119.2 . . ? C1 C6 C5 119.2(5) . . ? C1 C6 C7 123.6(5) . . ? C5 C6 C7 117.1(5) . . ? C8 C7 C6 110.9(4) . . ? C8 C7 C22 109.8(5) . . ? C6 C7 C22 109.4(5) . . ? C8 C7 C23 107.7(5) . . ? C6 C7 C23 110.1(5) . . ? C22 C7 C23 108.9(5) . . ? C9 C8 C13 117.0(5) . . ? C9 C8 C7 119.2(5) . . ? C13 C8 C7 123.8(5) . . ? C10 C9 C8 124.4(7) . . ? C10 C9 H9 117.8 . . ? C8 C9 H9 117.8 . . ? C9 C10 C11 117.2(6) . . ? C9 C10 H10 121.4 . . ? C11 C10 H10 121.4 . . ? C12 C11 C10 122.0(6) . . ? C12 C11 H11 119.0 . . ? C10 C11 H11 119.0 . . ? C11 C12 C13 119.9(6) . . ? C11 C12 C14 118.7(6) . . ? C13 C12 C14 121.4(6) . . ? N1 C13 C12 120.4(5) . . ? N1 C13 C8 120.2(5) . . ? C12 C13 C8 119.3(5) . . ? C12 C14 C15 110.6(5) . . ? C12 C14 C24 110.0(6) . . ? C15 C14 C24 111.1(6) . . ? C12 C14 C25 108.1(6) . . ? C15 C14 C25 107.7(5) . . ? C24 C14 C25 109.3(6) . . ? C16 C15 C20 118.1(7) . . ? C16 C15 C14 121.7(6) . . ? C20 C15 C14 119.5(5) . . ? C17 C16 C15 122.0(7) . . ? C17 C16 H16 119.0 . . ? C15 C16 H16 119.0 . . ? C16 C17 C18 118.9(6) . . ? C16 C17 H17 120.5 . . ? C18 C17 H17 120.5 . . ? C17 C18 C19 121.2(7) . . ? C17 C18 H18 119.4 . . ? C19 C18 H18 119.4 . . ? C18 C19 C20 118.9(6) . . ? C18 C19 C21 121.8(6) . . ? C20 C19 C21 119.1(5) . . ? C19 C20 C15 119.6(5) . . ? C19 C20 N1 120.3(5) . . ? C15 C20 N1 120.1(5) . . ? C19 C21 C2 107.0(5) . . ? C19 C21 C27 113.7(5) . . ? C2 C21 C27 112.9(5) . . ? C19 C21 C26 106.9(5) . . ? C2 C21 C26 108.5(5) . . ? C27 C21 C26 107.6(5) . . ? C7 C22 H22A 109.5 . . ? C7 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C7 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C7 C23 H23A 109.5 . . ? C7 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C7 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C14 C24 H24A 109.5 . . ? C14 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C14 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C14 C25 H25A 109.5 . . ? C14 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C14 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C21 C26 H26A 109.5 . . ? C21 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C21 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C21 C27 H27A 109.5 . . ? C21 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C21 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C29 C28 C33 119.5(5) . . ? C29 C28 N2 122.0(5) . . ? C33 C28 N2 118.4(5) . . ? C30 C29 C28 119.7(5) . . ? C30 C29 C48 117.3(5) . . ? C28 C29 C48 123.0(5) . . ? C29 C30 C31 121.1(6) . . ? C29 C30 H30 119.5 . . ? C31 C30 H30 119.5 . . ? C32 C31 C30 119.2(6) . . ? C32 C31 H31 120.4 . . ? C30 C31 H31 120.4 . . ? C31 C32 C33 121.7(6) . . ? C31 C32 H32 119.2 . . ? C33 C32 H32 119.2 . . ? C32 C33 C28 118.7(5) . . ? C32 C33 C34 121.7(5) . . ? C28 C33 C34 119.3(5) . . ? C33 C34 C35 107.1(4) . . ? C33 C34 C50 110.0(5) . . ? C35 C34 C50 107.9(5) . . ? C33 C34 C49 111.9(5) . . ? C35 C34 C49 111.7(5) . . ? C50 C34 C49 108.3(5) . . ? C36 C35 C40 119.0(6) . . ? C36 C35 C34 122.2(5) . . ? C40 C35 C34 118.5(5) . . ? C37 C36 C35 120.8(6) . . ? C37 C36 H36 119.6 . . ? C35 C36 H36 119.6 . . ? C36 C37 C38 119.2(6) . . ? C36 C37 H37 120.4 . . ? C38 C37 H37 120.4 . . ? C37 C38 C39 121.7(6) . . ? C37 C38 H38 119.1 . . ? C39 C38 H38 119.1 . . ? C40 C39 C38 117.6(6) . . ? C40 C39 C41 121.7(5) . . ? C38 C39 C41 120.3(5) . . ? C39 C40 C35 120.3(5) . . ? C39 C40 N2 120.2(5) . . ? C35 C40 N2 119.5(5) . . ? C42 C41 C39 111.1(5) . . ? C42 C41 C52 111.2(5) . . ? C39 C41 C52 111.4(6) . . ? C42 C41 C51 109.6(5) . . ? C39 C41 C51 105.6(5) . . ? C52 C41 C51 107.8(6) . . ? C43 C42 C47 119.4(5) . . ? C43 C42 C41 118.4(5) . . ? C47 C42 C41 122.2(5) . . ? C44 C43 C42 122.7(6) . . ? C44 C43 H43 118.6 . . ? C42 C43 H43 118.6 . . ? C43 C44 C45 117.1(6) . . ? C43 C44 H44 121.5 . . ? C45 C44 H44 121.5 . . ? C44 C45 C46 123.1(6) . . ? C44 C45 H45 118.5 . . ? C46 C45 H45 118.5 . . ? C45 C46 C47 118.6(5) . . ? C45 C46 C48 117.2(5) . . ? C47 C46 C48 124.2(5) . . ? C42 C47 C46 118.8(5) . . ? C42 C47 N2 120.6(5) . . ? C46 C47 N2 120.6(5) . . ? C46 C48 C29 110.6(4) . . ? C46 C48 C54 110.0(5) . . ? C29 C48 C54 107.4(5) . . ? C46 C48 C53 109.2(5) . . ? C29 C48 C53 109.4(5) . . ? C54 C48 C53 110.3(5) . . ? C34 C49 H49A 109.5 . . ? C34 C49 H49B 109.5 . . ? H49A C49 H49B 109.5 . . ? C34 C49 H49C 109.5 . . ? H49A C49 H49C 109.5 . . ? H49B C49 H49C 109.5 . . ? C34 C50 H50A 109.5 . . ? C34 C50 H50B 109.5 . . ? H50A C50 H50B 109.5 . . ? C34 C50 H50C 109.5 . . ? H50A C50 H50C 109.5 . . ? H50B C50 H50C 109.5 . . ? C41 C51 H51A 109.5 . . ? C41 C51 H51B 109.5 . . ? H51A C51 H51B 109.5 . . ? C41 C51 H51C 109.5 . . ? H51A C51 H51C 109.5 . . ? H51B C51 H51C 109.5 . . ? C41 C52 H52A 109.5 . . ? C41 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? C41 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? C48 C53 H53A 109.5 . . ? C48 C53 H53B 109.5 . . ? H53A C53 H53B 109.5 . . ? C48 C53 H53C 109.5 . . ? H53A C53 H53C 109.5 . . ? H53B C53 H53C 109.5 . . ? C48 C54 H54A 109.5 . . ? C48 C54 H54B 109.5 . . ? H54A C54 H54B 109.5 . . ? C48 C54 H54C 109.5 . . ? H54A C54 H54C 109.5 . . ? H54B C54 H54C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.395 _refine_diff_density_min -0.263 _refine_diff_density_rms 0.068