# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Chen-Hsiung Hung' _publ_contact_author_address ; Chemistry Academia Sinica Institute of Chemistry Academia Sinica Nankang Taipei 115 TAIWAN ; _publ_contact_author_email CHHUNG@CHEM.SINICA.EDU.TW _publ_section_title ; m-Benziporphodimethene: a New Porphyrin Analogue Fluorescence Zinc(II) Sensor ; loop_ _publ_author_name 'Chen-Hsiung Hung.' 'Gao-Fong Chang.' 'Han-Wei Chu.' 'Anil Kumar' ; Geng-Fong Lin ; 'Li-Yang Luo.' # Attachment 'i7793_mp.cif' data_i7793_mp _database_code_depnum_ccdc_archive 'CCDC 662990' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H32 Cl N3 Zn' _chemical_formula_weight 631.49 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 '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 11.8528(6) _cell_length_b 15.8042(9) _cell_length_c 16.9980(10) _cell_angle_alpha 90.00 _cell_angle_beta 109.888(3) _cell_angle_gamma 90.00 _cell_volume 2994.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Red _exptl_crystal_colour Block _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.401 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 0.942 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.8716 _exptl_absorpt_correction_T_max 0.9284 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 22519 _diffrn_reflns_av_R_equivalents 0.1092 _diffrn_reflns_av_sigmaI/netI 0.1308 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 25.17 _reflns_number_total 5336 _reflns_number_gt 3178 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0374P)^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 5336 _refine_ls_number_parameters 392 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1149 _refine_ls_R_factor_gt 0.0572 _refine_ls_wR_factor_ref 0.1415 _refine_ls_wR_factor_gt 0.1235 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _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 Zn1 Zn 0.57243(5) 0.72014(4) 0.25104(3) 0.02279(19) Uani 1 1 d . . . Cl1 Cl 0.76640(10) 0.73105(9) 0.26346(7) 0.0319(3) Uani 1 1 d . . . N1 N 0.4825(3) 0.7692(3) 0.1296(2) 0.0243(10) Uani 1 1 d . . . N2 N 0.5089(3) 0.8138(3) 0.3028(2) 0.0221(9) Uani 1 1 d . . . N3 N 0.5786(3) 0.6358(3) 0.3501(2) 0.0227(10) Uani 1 1 d . . . C1 C 0.4031(5) 0.4790(4) 0.1937(3) 0.0441(16) Uani 1 1 d . . . H1 H 0.3821 0.4398 0.2288 0.053 Uiso 1 1 calc R . . C2 C 0.3180(5) 0.5051(4) 0.1186(4) 0.0539(18) Uani 1 1 d . . . H2 H 0.2387 0.4834 0.1033 0.065 Uiso 1 1 calc R . . C3 C 0.3454(5) 0.5620(4) 0.0651(3) 0.0428(16) Uani 1 1 d . . . H3 H 0.2856 0.5804 0.0149 0.051 Uiso 1 1 calc R . . C4 C 0.4640(5) 0.5914(4) 0.0875(3) 0.0390(14) Uani 1 1 d . . . C5 C 0.4939(5) 0.6537(4) 0.0319(3) 0.0386(15) Uani 1 1 d . . . C6 C 0.4607(4) 0.7398(3) 0.0524(3) 0.0290(13) Uani 1 1 d . . . C7 C 0.4043(4) 0.8021(3) -0.0093(3) 0.0305(13) Uani 1 1 d . . . H7 H 0.3800 0.7953 -0.0683 0.037 Uiso 1 1 calc R . . C8 C 0.3923(4) 0.8723(3) 0.0318(3) 0.0276(13) Uani 1 1 d . . . H8 H 0.3578 0.9244 0.0073 0.033 Uiso 1 1 calc R . . C9 C 0.4412(4) 0.8539(3) 0.1198(3) 0.0221(11) Uani 1 1 d . . . C10 C 0.4394(4) 0.9096(3) 0.1817(3) 0.0207(11) Uani 1 1 d . . . C11 C 0.4773(4) 0.8918(3) 0.2695(3) 0.0236(12) Uani 1 1 d . . . C12 C 0.4815(4) 0.9514(3) 0.3315(3) 0.0308(13) Uani 1 1 d . . . H12 H 0.4647 1.0102 0.3239 0.037 Uiso 1 1 calc R . . C13 C 0.5151(4) 0.9069(3) 0.4057(3) 0.0315(13) Uani 1 1 d . . . H13 H 0.5258 0.9294 0.4596 0.038 Uiso 1 1 calc R . . C14 C 0.5306(4) 0.8221(3) 0.3869(3) 0.0244(12) Uani 1 1 d . . . C15 C 0.5574(4) 0.7526(3) 0.4433(3) 0.0218(11) Uani 1 1 d . . . C16 C 0.5747(4) 0.6699(3) 0.4262(3) 0.0203(11) Uani 1 1 d . . . C17 C 0.5919(4) 0.6024(3) 0.4851(3) 0.0250(12) Uani 1 1 d . . . H17 H 0.5928 0.6073 0.5410 0.030 Uiso 1 1 calc R . . C18 C 0.6065(4) 0.5309(3) 0.4469(3) 0.0257(12) Uani 1 1 d . . . H18 H 0.6197 0.4760 0.4710 0.031 Uiso 1 1 calc R . . C19 C 0.5986(4) 0.5525(3) 0.3639(3) 0.0219(11) Uani 1 1 d . . . C20 C 0.6115(5) 0.4888(3) 0.3011(3) 0.0277(12) Uani 1 1 d . . . C21 C 0.5195(5) 0.5111(4) 0.2167(3) 0.0347(14) Uani 1 1 d . . . C22 C 0.5472(4) 0.5653(3) 0.1627(3) 0.0244(12) Uani 1 1 d . . . H22 H 0.6271 0.5858 0.1777 0.029 Uiso 1 1 calc R . . C23 C 0.6315(5) 0.6534(4) 0.0455(3) 0.0458(16) Uani 1 1 d . . . H23A H 0.6756 0.6790 0.0998 0.069 Uiso 1 1 calc R . . H23B H 0.6461 0.6860 0.0009 0.069 Uiso 1 1 calc R . . H23C H 0.6588 0.5950 0.0444 0.069 Uiso 1 1 calc R . . C24 C 0.4317(5) 0.6320(4) -0.0605(3) 0.0535(18) Uani 1 1 d . . . H24A H 0.4491 0.5731 -0.0704 0.080 Uiso 1 1 calc R . . H24B H 0.4613 0.6695 -0.0950 0.080 Uiso 1 1 calc R . . H24C H 0.3449 0.6394 -0.0752 0.080 Uiso 1 1 calc R . . C25 C 0.7398(5) 0.4937(4) 0.2999(3) 0.0445(16) Uani 1 1 d . . . H25A H 0.7619 0.5530 0.2969 0.067 Uiso 1 1 calc R . . H25B H 0.7448 0.4631 0.2511 0.067 Uiso 1 1 calc R . . H25C H 0.7949 0.4680 0.3511 0.067 Uiso 1 1 calc R . . C26 C 0.5900(6) 0.4003(4) 0.3270(3) 0.0528(17) Uani 1 1 d . . . H26A H 0.6574 0.3834 0.3765 0.079 Uiso 1 1 calc R . . H26B H 0.5830 0.3609 0.2811 0.079 Uiso 1 1 calc R . . H26C H 0.5157 0.3994 0.3402 0.079 Uiso 1 1 calc R . . C27 C 0.3826(4) 0.9928(3) 0.1546(3) 0.0221(11) Uani 1 1 d . . . C28 C 0.4254(4) 1.0510(3) 0.1107(3) 0.0285(13) Uani 1 1 d . . . H28 H 0.4975 1.0395 0.0999 0.034 Uiso 1 1 calc R . . C29 C 0.3637(5) 1.1260(4) 0.0824(3) 0.0352(14) Uani 1 1 d . . . H29 H 0.3936 1.1653 0.0520 0.042 Uiso 1 1 calc R . . C30 C 0.2598(4) 1.1437(3) 0.0980(3) 0.0339(13) Uani 1 1 d . . . H30 H 0.2172 1.1946 0.0777 0.041 Uiso 1 1 calc R . . C31 C 0.2181(4) 1.0881(3) 0.1429(3) 0.0279(12) Uani 1 1 d . . . H31 H 0.1471 1.1006 0.1547 0.034 Uiso 1 1 calc R . . C32 C 0.2787(4) 1.0138(3) 0.1710(3) 0.0279(13) Uani 1 1 d . . . H32 H 0.2489 0.9758 0.2026 0.034 Uiso 1 1 calc R . . C33 C 0.5638(4) 0.7728(3) 0.5307(3) 0.0218(11) Uani 1 1 d . . . C34 C 0.4632(4) 0.8026(3) 0.5473(3) 0.0266(12) Uani 1 1 d . . . H34 H 0.3918 0.8148 0.5021 0.032 Uiso 1 1 calc R . . C35 C 0.4659(5) 0.8145(3) 0.6282(3) 0.0343(14) Uani 1 1 d . . . H35 H 0.3957 0.8322 0.6386 0.041 Uiso 1 1 calc R . . C36 C 0.5708(5) 0.8007(3) 0.6940(3) 0.0369(14) Uani 1 1 d . . . H36 H 0.5731 0.8097 0.7498 0.044 Uiso 1 1 calc R . . C37 C 0.6719(5) 0.7740(3) 0.6792(3) 0.0361(14) Uani 1 1 d . . . H37 H 0.7444 0.7660 0.7248 0.043 Uiso 1 1 calc R . . C38 C 0.6690(4) 0.7588(3) 0.5986(3) 0.0286(13) Uani 1 1 d . . . H38 H 0.7389 0.7387 0.5892 0.034 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 Zn1 0.0274(3) 0.0216(4) 0.0201(3) -0.0002(3) 0.0091(2) 0.0009(3) Cl1 0.0291(6) 0.0395(9) 0.0284(6) -0.0004(6) 0.0115(5) -0.0059(6) N1 0.029(2) 0.025(3) 0.019(2) -0.0034(18) 0.0078(17) 0.002(2) N2 0.030(2) 0.016(3) 0.020(2) 0.0003(18) 0.0081(17) 0.0003(19) N3 0.026(2) 0.023(3) 0.020(2) -0.0031(18) 0.0090(17) -0.0020(19) C1 0.047(4) 0.052(5) 0.047(4) -0.006(3) 0.034(3) -0.006(3) C2 0.037(4) 0.062(5) 0.062(4) -0.030(4) 0.016(3) -0.010(3) C3 0.033(3) 0.061(5) 0.030(3) -0.004(3) 0.005(3) 0.003(3) C4 0.051(4) 0.032(4) 0.028(3) -0.006(3) 0.007(3) 0.007(3) C5 0.058(4) 0.037(4) 0.020(3) -0.001(3) 0.011(3) 0.016(3) C6 0.032(3) 0.031(4) 0.024(3) 0.004(2) 0.010(2) 0.007(3) C7 0.031(3) 0.040(4) 0.019(3) -0.003(2) 0.006(2) 0.006(3) C8 0.030(3) 0.028(4) 0.024(3) 0.008(2) 0.007(2) 0.010(2) C9 0.021(3) 0.023(3) 0.021(3) 0.006(2) 0.006(2) 0.005(2) C10 0.020(3) 0.020(3) 0.023(3) 0.005(2) 0.009(2) -0.001(2) C11 0.030(3) 0.019(3) 0.020(3) -0.002(2) 0.007(2) 0.003(2) C12 0.050(3) 0.013(3) 0.027(3) -0.003(2) 0.010(2) 0.000(3) C13 0.038(3) 0.032(4) 0.024(3) -0.004(3) 0.009(2) 0.002(3) C14 0.029(3) 0.026(3) 0.021(3) -0.005(2) 0.012(2) 0.003(2) C15 0.027(3) 0.021(3) 0.018(2) -0.004(2) 0.009(2) -0.003(2) C16 0.020(2) 0.025(3) 0.019(2) -0.002(2) 0.010(2) -0.002(2) C17 0.029(3) 0.026(3) 0.020(2) 0.002(2) 0.009(2) -0.003(2) C18 0.032(3) 0.021(3) 0.025(3) 0.007(2) 0.011(2) 0.006(2) C19 0.026(3) 0.015(3) 0.026(3) 0.003(2) 0.009(2) 0.000(2) C20 0.044(3) 0.017(3) 0.027(3) 0.000(2) 0.018(2) 0.006(3) C21 0.039(3) 0.034(4) 0.039(3) -0.011(3) 0.022(3) -0.003(3) C22 0.033(3) 0.014(3) 0.028(3) -0.003(2) 0.012(2) 0.000(2) C23 0.052(4) 0.049(4) 0.044(3) 0.004(3) 0.026(3) 0.009(3) C24 0.087(5) 0.044(4) 0.021(3) -0.005(3) 0.007(3) 0.009(4) C25 0.044(3) 0.050(4) 0.042(3) 0.007(3) 0.018(3) 0.014(3) C26 0.085(5) 0.029(4) 0.056(4) -0.012(3) 0.039(4) -0.006(4) C27 0.028(3) 0.018(3) 0.020(2) -0.003(2) 0.008(2) 0.000(2) C28 0.030(3) 0.028(4) 0.031(3) 0.001(2) 0.016(2) -0.001(3) C29 0.046(3) 0.026(4) 0.033(3) 0.008(3) 0.013(3) -0.001(3) C30 0.040(3) 0.020(3) 0.032(3) 0.000(3) -0.001(2) 0.006(3) C31 0.027(3) 0.024(3) 0.030(3) -0.006(2) 0.007(2) 0.000(3) C32 0.029(3) 0.035(4) 0.020(3) -0.001(2) 0.009(2) -0.002(3) C33 0.034(3) 0.015(3) 0.020(2) -0.003(2) 0.014(2) -0.005(2) C34 0.026(3) 0.027(3) 0.027(3) -0.007(2) 0.009(2) -0.003(2) C35 0.043(3) 0.030(4) 0.039(3) -0.014(3) 0.025(3) -0.010(3) C36 0.051(3) 0.039(4) 0.023(3) -0.006(3) 0.017(3) -0.009(3) C37 0.042(3) 0.040(4) 0.020(3) -0.003(3) 0.003(2) -0.003(3) C38 0.032(3) 0.027(4) 0.026(3) -0.002(2) 0.009(2) 0.002(2) _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 Zn1 N2 1.995(4) . ? Zn1 N1 2.121(4) . ? Zn1 N3 2.130(4) . ? Zn1 Cl1 2.2428(13) . ? N1 C6 1.332(6) . ? N1 C9 1.416(6) . ? N2 C11 1.355(6) . ? N2 C14 1.371(5) . ? N3 C19 1.344(6) . ? N3 C16 1.417(5) . ? C1 C2 1.394(8) . ? C1 C21 1.396(7) . ? C1 H1 0.9500 . ? C2 C3 1.393(8) . ? C2 H2 0.9500 . ? C3 C4 1.405(7) . ? C3 H3 0.9500 . ? C4 C22 1.386(6) . ? C4 C5 1.488(7) . ? C5 C6 1.491(7) . ? C5 C24 1.529(6) . ? C5 C23 1.567(7) . ? C6 C7 1.429(7) . ? C7 C8 1.345(6) . ? C7 H7 0.9500 . ? C8 C9 1.439(6) . ? C8 H8 0.9500 . ? C9 C10 1.378(6) . ? C10 C11 1.432(6) . ? C10 C27 1.478(6) . ? C11 C12 1.401(6) . ? C12 C13 1.380(6) . ? C12 H12 0.9500 . ? C13 C14 1.404(7) . ? C13 H13 0.9500 . ? C14 C15 1.420(6) . ? C15 C16 1.370(6) . ? C15 C33 1.497(6) . ? C16 C17 1.428(6) . ? C17 C18 1.344(6) . ? C17 H17 0.9500 . ? C18 C19 1.424(6) . ? C18 H18 0.9500 . ? C19 C20 1.512(6) . ? C20 C26 1.514(7) . ? C20 C21 1.519(7) . ? C20 C25 1.530(6) . ? C21 C22 1.374(7) . ? C22 H22 0.9500 . ? 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 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 C28 1.384(6) . ? C27 C32 1.392(6) . ? C28 C29 1.391(7) . ? C28 H28 0.9500 . ? C29 C30 1.375(7) . ? C29 H29 0.9500 . ? C30 C31 1.362(7) . ? C30 H30 0.9500 . ? C31 C32 1.373(7) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? C33 C34 1.397(6) . ? C33 C38 1.399(6) . ? C34 C35 1.377(6) . ? C34 H34 0.9500 . ? C35 C36 1.377(7) . ? C35 H35 0.9500 . ? C36 C37 1.372(7) . ? C36 H36 0.9500 . ? C37 C38 1.379(6) . ? C37 H37 0.9500 . ? C38 H38 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 N2 Zn1 N1 91.02(14) . . ? N2 Zn1 N3 91.87(15) . . ? N1 Zn1 N3 150.32(14) . . ? N2 Zn1 Cl1 115.46(11) . . ? N1 Zn1 Cl1 102.89(10) . . ? N3 Zn1 Cl1 102.44(10) . . ? C6 N1 C9 105.7(4) . . ? C6 N1 Zn1 134.1(3) . . ? C9 N1 Zn1 119.9(3) . . ? C11 N2 C14 106.0(4) . . ? C11 N2 Zn1 125.7(3) . . ? C14 N2 Zn1 124.5(3) . . ? C19 N3 C16 105.8(4) . . ? C19 N3 Zn1 135.1(3) . . ? C16 N3 Zn1 118.7(3) . . ? C2 C1 C21 119.2(5) . . ? C2 C1 H1 120.4 . . ? C21 C1 H1 120.4 . . ? C3 C2 C1 122.2(5) . . ? C3 C2 H2 118.9 . . ? C1 C2 H2 118.9 . . ? C2 C3 C4 118.1(5) . . ? C2 C3 H3 121.0 . . ? C4 C3 H3 121.0 . . ? C22 C4 C3 119.0(5) . . ? C22 C4 C5 122.3(5) . . ? C3 C4 C5 118.7(5) . . ? C4 C5 C6 108.4(4) . . ? C4 C5 C24 111.6(5) . . ? C6 C5 C24 111.8(4) . . ? C4 C5 C23 111.4(4) . . ? C6 C5 C23 108.2(5) . . ? C24 C5 C23 105.4(4) . . ? N1 C6 C7 111.6(4) . . ? N1 C6 C5 124.8(4) . . ? C7 C6 C5 123.5(4) . . ? C8 C7 C6 107.0(4) . . ? C8 C7 H7 126.5 . . ? C6 C7 H7 126.5 . . ? C7 C8 C9 107.3(4) . . ? C7 C8 H8 126.4 . . ? C9 C8 H8 126.4 . . ? C10 C9 N1 127.5(4) . . ? C10 C9 C8 124.0(5) . . ? N1 C9 C8 108.4(4) . . ? C9 C10 C11 126.1(5) . . ? C9 C10 C27 117.0(4) . . ? C11 C10 C27 116.6(4) . . ? N2 C11 C12 111.3(4) . . ? N2 C11 C10 123.9(4) . . ? C12 C11 C10 124.7(5) . . ? C13 C12 C11 105.7(5) . . ? C13 C12 H12 127.2 . . ? C11 C12 H12 127.2 . . ? C12 C13 C14 107.3(4) . . ? C12 C13 H13 126.3 . . ? C14 C13 H13 126.3 . . ? N2 C14 C13 109.7(4) . . ? N2 C14 C15 123.3(4) . . ? C13 C14 C15 126.9(4) . . ? C16 C15 C14 127.6(4) . . ? C16 C15 C33 117.0(4) . . ? C14 C15 C33 115.4(4) . . ? C15 C16 N3 127.6(4) . . ? C15 C16 C17 124.0(4) . . ? N3 C16 C17 108.4(4) . . ? C18 C17 C16 107.5(4) . . ? C18 C17 H17 126.3 . . ? C16 C17 H17 126.3 . . ? C17 C18 C19 107.5(4) . . ? C17 C18 H18 126.2 . . ? C19 C18 H18 126.2 . . ? N3 C19 C18 110.8(4) . . ? N3 C19 C20 125.6(4) . . ? C18 C19 C20 123.5(5) . . ? C19 C20 C26 110.0(4) . . ? C19 C20 C21 107.5(4) . . ? C26 C20 C21 110.6(5) . . ? C19 C20 C25 108.4(4) . . ? C26 C20 C25 108.4(4) . . ? C21 C20 C25 111.9(4) . . ? C22 C21 C1 118.6(5) . . ? C22 C21 C20 121.2(5) . . ? C1 C21 C20 120.2(5) . . ? C21 C22 C4 123.0(5) . . ? C21 C22 H22 118.5 . . ? C4 C22 H22 118.5 . . ? C5 C23 H23A 109.5 . . ? C5 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C5 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C5 C24 H24A 109.5 . . ? C5 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C5 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C20 C25 H25A 109.5 . . ? C20 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C20 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C20 C26 H26A 109.5 . . ? C20 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C20 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C28 C27 C32 117.5(5) . . ? C28 C27 C10 123.2(4) . . ? C32 C27 C10 119.3(4) . . ? C27 C28 C29 120.4(5) . . ? C27 C28 H28 119.8 . . ? C29 C28 H28 119.8 . . ? C30 C29 C28 120.5(5) . . ? C30 C29 H29 119.8 . . ? C28 C29 H29 119.8 . . ? C31 C30 C29 119.8(5) . . ? C31 C30 H30 120.1 . . ? C29 C30 H30 120.1 . . ? C30 C31 C32 120.0(5) . . ? C30 C31 H31 120.0 . . ? C32 C31 H31 120.0 . . ? C31 C32 C27 121.8(5) . . ? C31 C32 H32 119.1 . . ? C27 C32 H32 119.1 . . ? C34 C33 C38 118.0(4) . . ? C34 C33 C15 120.9(4) . . ? C38 C33 C15 121.0(4) . . ? C35 C34 C33 121.1(5) . . ? C35 C34 H34 119.5 . . ? C33 C34 H34 119.5 . . ? C34 C35 C36 119.8(5) . . ? C34 C35 H35 120.1 . . ? C36 C35 H35 120.1 . . ? C37 C36 C35 120.2(5) . . ? C37 C36 H36 119.9 . . ? C35 C36 H36 119.9 . . ? C36 C37 C38 120.5(5) . . ? C36 C37 H37 119.8 . . ? C38 C37 H37 119.8 . . ? C37 C38 C33 120.4(5) . . ? C37 C38 H38 119.8 . . ? C33 C38 H38 119.8 . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.17 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.717 _refine_diff_density_min -0.474 _refine_diff_density_rms 0.094