# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 # cg010029u.cif data_global _audit_creation_method 'SHELXL-97 plus manual editing' _publ_contact_author_name 'Andrew Bond' _publ_contact_author_address ; Department of Chemistry University of Cambridge Lensfield Road Cambridge CB2 1EW UK ; _publ_contact_author_email adb29@cam.ac.uk _publ_contact_author_fax '(01223) 336362' _publ_contact_author_phone '(01223) 336352' ############################# ## denoted 1 in the text ## ############################# data_js9946 _chemical_name_systematic ; 5,15-diphenylporphyrin ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H22 N4' _chemical_formula_sum 'C32 H22 N4' _chemical_formula_weight 462.54 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 14.5219(9) _cell_length_b 16.7635(10) _cell_length_c 9.6313(6) _cell_angle_alpha 90.00 _cell_angle_beta 105.455(2) _cell_angle_gamma 90.00 _cell_volume 2259.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 11473 _cell_measurement_theta_min 3.05 _cell_measurement_theta_max 29.39 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.359 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9871 _exptl_absorpt_correction_T_max 0.9984 _exptl_absorpt_process_details ; Correction applied by SADABS - note that the transmission factors are not real since they include corrections for beam decay and possibly crystal decay (the two cannot be distinguished). The numbers listed in the CIF are those calculated by SHELXL. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.6893 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Daresbury SRS, Station 9.8' _diffrn_radiation_monochromator 'Silicon 111' _diffrn_measurement_device_type 'Bruker SMART CCD' _diffrn_measurement_method 'Thin slice \w-scans' _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number 0 _diffrn_reflns_number 14722 _diffrn_reflns_av_R_equivalents 0.0357 _diffrn_reflns_av_sigmaI/netI 0.0453 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 29.51 _diffrn_measured_fraction_theta_max 0.902 _diffrn_reflns_theta_full 29.51 _diffrn_measured_fraction_theta_full 0.902 _reflns_number_total 6238 _reflns_number_gt 5142 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Bruker AXS, 1994)' _computing_cell_refinement 'LSCELL (CLEGG, 1997)' _computing_data_reduction 'Bruker SAINT (Bruker AXS, 1994)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (Sheldrick, 1993)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. N-H hydrogen atoms were located from the Fourier difference map, and their coordinates allowed to refine freely. The two atoms were refined with a common isotropic temperature factor. ; _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^)+(0.0744P)^2^+0.4317P] 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 6238 _refine_ls_number_parameters 332 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0632 _refine_ls_R_factor_gt 0.0493 _refine_ls_wR_factor_ref 0.1317 _refine_ls_wR_factor_gt 0.1278 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.018 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.424 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.050 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 0.37194(7) 0.34084(6) 0.65667(11) 0.0201(2) Uani 1 1 d . . . H1A H 0.3372(16) 0.3543(14) 0.562(3) 0.074(5) Uiso 1 1 d . . . N2 N 0.39596(7) 0.38693(6) 0.39375(10) 0.0197(2) Uani 1 1 d . . . N3 N 0.17941(7) 0.38989(6) 0.26013(11) 0.0191(2) Uani 1 1 d . . . H3A H 0.2153(17) 0.3750(15) 0.352(3) 0.074(5) Uiso 1 1 d . . . N4 N 0.15606(7) 0.34738(6) 0.52445(10) 0.01893(19) Uani 1 1 d . . . C1 C 0.33755(8) 0.31737(7) 0.76982(12) 0.0202(2) Uani 1 1 d . . . C2 C 0.41789(8) 0.30686(7) 0.89181(13) 0.0227(2) Uani 1 1 d . . . H2 H 0.4157 0.2910 0.9856 0.027 Uiso 1 1 calc R . . C3 C 0.49824(8) 0.32363(8) 0.84967(13) 0.0231(2) Uani 1 1 d . . . H3 H 0.5619 0.3220 0.9092 0.028 Uiso 1 1 calc R . . C4 C 0.46983(8) 0.34419(7) 0.70000(12) 0.0198(2) Uani 1 1 d . . . C5 C 0.52826(8) 0.36255(7) 0.60929(12) 0.0192(2) Uani 1 1 d . . . C6 C 0.49114(8) 0.38271(7) 0.46286(12) 0.0195(2) Uani 1 1 d . . . C7 C 0.54800(8) 0.39612(8) 0.36149(13) 0.0238(2) Uani 1 1 d . . . H7 H 0.6157 0.3963 0.3826 0.029 Uiso 1 1 calc R . . C8 C 0.48565(9) 0.40819(8) 0.23163(13) 0.0253(3) Uani 1 1 d . . . H8 H 0.5010 0.4190 0.1435 0.030 Uiso 1 1 calc R . . C9 C 0.39099(8) 0.40155(7) 0.25259(13) 0.0210(2) Uani 1 1 d . . . C10 C 0.30842(8) 0.40935(8) 0.14016(12) 0.0223(2) Uani 1 1 d . . . H10 H 0.3184 0.4186 0.0480 0.027 Uiso 1 1 calc R . . C11 C 0.21373(8) 0.40553(7) 0.14336(12) 0.0202(2) Uani 1 1 d . . . C12 C 0.13356(8) 0.42213(7) 0.02403(13) 0.0227(2) Uani 1 1 d . . . H12 H 0.1356 0.4338 -0.0716 0.027 Uiso 1 1 calc R . . C13 C 0.05366(8) 0.41812(7) 0.07239(13) 0.0214(2) Uani 1 1 d . . . H13 H -0.0099 0.4277 0.0166 0.026 Uiso 1 1 calc R . . C14 C 0.08194(8) 0.39708(7) 0.22158(12) 0.0185(2) Uani 1 1 d . . . C15 C 0.02422(8) 0.38525(7) 0.31629(12) 0.0179(2) Uani 1 1 d . . . C16 C 0.06108(8) 0.35760(7) 0.45856(12) 0.0185(2) Uani 1 1 d . . . C17 C 0.00371(8) 0.33360(7) 0.55423(13) 0.0216(2) Uani 1 1 d . . . H17 H -0.0640 0.3347 0.5338 0.026 Uiso 1 1 calc R . . C18 C 0.06590(8) 0.30934(7) 0.67818(13) 0.0223(2) Uani 1 1 d . . . H18 H 0.0503 0.2896 0.7615 0.027 Uiso 1 1 calc R . . C19 C 0.16067(8) 0.31934(7) 0.65917(12) 0.0198(2) Uani 1 1 d . . . C20 C 0.24297(8) 0.30583(7) 0.76968(13) 0.0211(2) Uani 1 1 d . . . H20 H 0.2330 0.2860 0.8569 0.025 Uiso 1 1 calc R . . C21 C 0.63304(8) 0.35285(7) 0.66793(12) 0.0196(2) Uani 1 1 d . . . C22 C 0.66937(8) 0.28027(7) 0.72990(13) 0.0238(2) Uani 1 1 d . . . H22 H 0.6267 0.2382 0.7353 0.029 Uiso 1 1 calc R . . C23 C 0.76693(9) 0.26876(8) 0.78374(14) 0.0277(3) Uani 1 1 d . . . H23 H 0.7906 0.2195 0.8278 0.033 Uiso 1 1 calc R . . C24 C 0.82974(9) 0.32911(9) 0.77317(14) 0.0299(3) Uani 1 1 d . . . H24 H 0.8967 0.3209 0.8080 0.036 Uiso 1 1 calc R . . C25 C 0.79507(9) 0.40131(8) 0.71188(15) 0.0288(3) Uani 1 1 d . . . H25 H 0.8383 0.4427 0.7050 0.035 Uiso 1 1 calc R . . C26 C 0.69725(9) 0.41378(7) 0.66013(13) 0.0237(2) Uani 1 1 d . . . H26 H 0.6739 0.4638 0.6193 0.028 Uiso 1 1 calc R . . C27 C -0.07922(8) 0.40447(7) 0.26377(12) 0.0188(2) Uani 1 1 d . . . C28 C -0.13646(8) 0.37309(7) 0.13531(13) 0.0222(2) Uani 1 1 d . . . H28 H -0.1099 0.3362 0.0818 0.027 Uiso 1 1 calc R . . C29 C -0.23159(8) 0.39512(8) 0.08500(14) 0.0263(3) Uani 1 1 d . . . H29 H -0.2690 0.3749 -0.0045 0.032 Uiso 1 1 calc R . . C30 C -0.27239(8) 0.44651(8) 0.16471(14) 0.0273(3) Uani 1 1 d . . . H30 H -0.3379 0.4607 0.1309 0.033 Uiso 1 1 calc R . . C31 C -0.21719(8) 0.47697(8) 0.29361(14) 0.0253(2) Uani 1 1 d . . . H31 H -0.2451 0.5116 0.3491 0.030 Uiso 1 1 calc R . . C32 C -0.12121(8) 0.45703(7) 0.34213(13) 0.0221(2) Uani 1 1 d . . . H32 H -0.0835 0.4793 0.4296 0.026 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 0.0166(4) 0.0277(5) 0.0160(5) 0.0020(4) 0.0043(3) 0.0021(3) N2 0.0172(4) 0.0262(5) 0.0156(4) 0.0012(4) 0.0043(3) 0.0026(3) N3 0.0164(4) 0.0250(5) 0.0161(4) 0.0025(4) 0.0047(3) 0.0016(3) N4 0.0167(4) 0.0246(5) 0.0152(4) 0.0006(3) 0.0038(3) 0.0006(3) C1 0.0197(5) 0.0250(5) 0.0157(5) 0.0018(4) 0.0047(4) 0.0033(4) C2 0.0214(5) 0.0305(6) 0.0153(5) 0.0032(4) 0.0038(4) 0.0046(4) C3 0.0194(5) 0.0314(6) 0.0173(5) 0.0005(4) 0.0028(4) 0.0028(4) C4 0.0173(5) 0.0240(5) 0.0176(5) -0.0007(4) 0.0038(4) 0.0020(4) C5 0.0159(5) 0.0229(5) 0.0183(5) -0.0012(4) 0.0038(4) 0.0013(4) C6 0.0173(5) 0.0235(5) 0.0185(5) -0.0013(4) 0.0060(4) 0.0011(4) C7 0.0169(5) 0.0342(6) 0.0218(6) -0.0007(5) 0.0078(4) -0.0002(4) C8 0.0194(5) 0.0397(7) 0.0190(6) 0.0005(5) 0.0088(4) -0.0010(5) C9 0.0181(5) 0.0286(6) 0.0179(5) 0.0003(4) 0.0076(4) 0.0012(4) C10 0.0196(5) 0.0326(6) 0.0159(5) 0.0024(4) 0.0069(4) 0.0018(4) C11 0.0190(5) 0.0261(5) 0.0155(5) 0.0017(4) 0.0044(4) 0.0013(4) C12 0.0207(5) 0.0306(6) 0.0158(5) 0.0034(4) 0.0033(4) -0.0007(4) C13 0.0186(5) 0.0270(6) 0.0170(5) 0.0036(4) 0.0021(4) 0.0001(4) C14 0.0176(5) 0.0205(5) 0.0172(5) 0.0004(4) 0.0042(4) 0.0003(4) C15 0.0154(5) 0.0211(5) 0.0171(5) -0.0012(4) 0.0038(4) -0.0010(4) C16 0.0168(5) 0.0214(5) 0.0173(5) -0.0017(4) 0.0049(4) -0.0012(4) C17 0.0159(5) 0.0285(6) 0.0219(6) 0.0015(4) 0.0077(4) -0.0022(4) C18 0.0189(5) 0.0293(6) 0.0202(6) 0.0033(4) 0.0077(4) -0.0015(4) C19 0.0191(5) 0.0228(5) 0.0184(5) 0.0009(4) 0.0068(4) -0.0003(4) C20 0.0210(5) 0.0257(5) 0.0177(5) 0.0036(4) 0.0071(4) 0.0019(4) C21 0.0152(5) 0.0252(5) 0.0179(5) -0.0030(4) 0.0035(4) 0.0008(4) C22 0.0208(5) 0.0256(6) 0.0241(6) -0.0026(4) 0.0047(4) 0.0020(4) C23 0.0235(6) 0.0331(7) 0.0248(6) -0.0035(5) 0.0032(5) 0.0087(5) C24 0.0164(5) 0.0470(8) 0.0255(6) -0.0090(5) 0.0043(4) 0.0039(5) C25 0.0208(6) 0.0384(7) 0.0278(7) -0.0083(5) 0.0078(5) -0.0072(5) C26 0.0228(6) 0.0257(6) 0.0223(6) -0.0032(4) 0.0055(4) -0.0016(4) C27 0.0152(5) 0.0220(5) 0.0190(5) 0.0015(4) 0.0045(4) -0.0023(4) C28 0.0192(5) 0.0279(6) 0.0191(5) 0.0001(4) 0.0044(4) -0.0040(4) C29 0.0175(5) 0.0391(7) 0.0203(6) 0.0032(5) 0.0015(4) -0.0061(5) C30 0.0152(5) 0.0358(7) 0.0303(7) 0.0092(5) 0.0052(4) -0.0001(4) C31 0.0202(5) 0.0273(6) 0.0303(6) 0.0023(5) 0.0100(5) 0.0019(4) C32 0.0192(5) 0.0249(5) 0.0220(6) -0.0012(4) 0.0053(4) -0.0016(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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) - 1.2444 (0.0049) x + 16.1391 (0.0019) y + 2.6005 (0.0034) z = 6.7608 (0.0016) * -0.0151 (0.0005) N1 * 0.0151 (0.0005) N2 * -0.0151 (0.0005) N3 * 0.0152 (0.0005) N4 -0.0568 (0.0017) C1 -0.0093 (0.0020) C2 0.0519 (0.0020) C3 0.0298 (0.0016) C4 0.0175 (0.0017) C5 0.0083 (0.0016) C6 -0.1096 (0.0020) C7 -0.1749 (0.0021) C8 -0.1099 (0.0017) C9 -0.1735 (0.0018) C10 -0.1091 (0.0017) C11 -0.0518 (0.0021) C12 0.1087 (0.0020) C13 0.1219 (0.0016) C14 0.2492 (0.0017) C15 0.1269 (0.0016) C16 0.0599 (0.0020) C17 -0.0868 (0.0020) C18 -0.0928 (0.0017) C19 -0.1258 (0.0018) C20 Rms deviation of fitted atoms = 0.0151 - 4.1676 (0.0071) x + 5.6958 (0.0083) y + 9.0509 (0.0018) z = 5.4189 (0.0058) Angle to porphyrin plane (with approximate esd) = 54.45 ( 0.04 ) * -0.0021 (0.0008) C21 * -0.0060 (0.0009) C22 * 0.0093 (0.0009) C23 * -0.0045 (0.0009) C24 * -0.0035 (0.0009) C25 * 0.0068 (0.0009) C26 Rms deviation of fitted atoms = 0.0058 5.7143 (0.0065) x + 12.9980 (0.0054) y - 5.5950 (0.0040) z = 3.3256 (0.0037) Angle to porphyrin plane (with approximate esd) = 54.12 ( 0.03 ) * 0.0033 (0.0008) C27 * -0.0129 (0.0008) C28 * 0.0112 (0.0009) C29 * 0.0001 (0.0009) C30 * -0.0097 (0.0009) C31 * 0.0080 (0.0008) C32 Rms deviation of fitted atoms = 0.0088 ; 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 C1 1.3717(14) . ? N1 C4 1.3718(14) . ? N1 H1A 0.94(2) . ? N2 C9 1.3642(15) . ? N2 C6 1.3668(14) . ? N3 C14 1.3696(14) . ? N3 C11 1.3714(14) . ? N3 H3A 0.94(2) . ? N4 C19 1.3649(15) . ? N4 C16 1.3668(14) . ? C1 C20 1.3866(16) . ? C1 C2 1.4290(16) . ? C2 C3 1.3630(16) . ? C2 H2 0.9500 . ? C3 C4 1.4318(16) . ? C3 H3 0.9500 . ? C4 C5 1.4046(15) . ? C5 C6 1.4102(16) . ? C5 C21 1.4841(15) . ? C6 C7 1.4544(15) . ? C7 C8 1.3497(17) . ? C7 H7 0.9500 . ? C8 C9 1.4459(16) . ? C8 H8 0.9500 . ? C9 C10 1.3912(16) . ? C10 C11 1.3851(16) . ? C10 H10 0.9500 . ? C11 C12 1.4285(16) . ? C12 C13 1.3621(16) . ? C12 H12 0.9500 . ? C13 C14 1.4294(16) . ? C13 H13 0.9500 . ? C14 C15 1.4078(15) . ? C15 C16 1.4100(16) . ? C15 C27 1.4869(15) . ? C16 C17 1.4540(15) . ? C17 C18 1.3534(17) . ? C17 H17 0.9500 . ? C18 C19 1.4456(15) . ? C18 H18 0.9500 . ? C19 C20 1.3909(16) . ? C20 H20 0.9500 . ? C21 C22 1.3953(17) . ? C21 C26 1.3984(16) . ? C22 C23 1.3863(16) . ? C22 H22 0.9500 . ? C23 C24 1.384(2) . ? C23 H23 0.9500 . ? C24 C25 1.381(2) . ? C24 H24 0.9500 . ? C25 C26 1.3902(17) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 C28 1.3965(16) . ? C27 C32 1.4010(16) . ? C28 C29 1.3867(16) . ? C28 H28 0.9500 . ? C29 C30 1.3874(19) . ? C29 H29 0.9500 . ? C30 C31 1.3835(19) . ? C30 H30 0.9500 . ? C31 C32 1.3877(16) . ? C31 H31 0.9500 . ? C32 H32 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 C1 N1 C4 109.71(9) . . ? C1 N1 H1A 128.3(15) . . ? C4 N1 H1A 122.0(14) . . ? C9 N2 C6 105.83(9) . . ? C14 N3 C11 109.63(9) . . ? C14 N3 H3A 123.7(15) . . ? C11 N3 H3A 126.7(15) . . ? C19 N4 C16 105.80(9) . . ? N1 C1 C20 127.55(11) . . ? N1 C1 C2 107.35(10) . . ? C20 C1 C2 125.10(11) . . ? C3 C2 C1 107.81(10) . . ? C3 C2 H2 126.1 . . ? C1 C2 H2 126.1 . . ? C2 C3 C4 108.03(10) . . ? C2 C3 H3 126.0 . . ? C4 C3 H3 126.0 . . ? N1 C4 C5 124.65(10) . . ? N1 C4 C3 107.08(10) . . ? C5 C4 C3 128.25(10) . . ? C4 C5 C6 122.77(10) . . ? C4 C5 C21 117.86(10) . . ? C6 C5 C21 119.13(10) . . ? N2 C6 C5 124.54(10) . . ? N2 C6 C7 110.27(10) . . ? C5 C6 C7 125.05(10) . . ? C8 C7 C6 106.53(10) . . ? C8 C7 H7 126.7 . . ? C6 C7 H7 126.7 . . ? C7 C8 C9 106.68(11) . . ? C7 C8 H8 126.7 . . ? C9 C8 H8 126.7 . . ? N2 C9 C10 126.75(10) . . ? N2 C9 C8 110.68(10) . . ? C10 C9 C8 122.57(11) . . ? C11 C10 C9 129.28(11) . . ? C11 C10 H10 115.4 . . ? C9 C10 H10 115.4 . . ? N3 C11 C10 127.37(11) . . ? N3 C11 C12 107.49(10) . . ? C10 C11 C12 125.05(11) . . ? C13 C12 C11 107.53(10) . . ? C13 C12 H12 126.2 . . ? C11 C12 H12 126.2 . . ? C12 C13 C14 108.25(10) . . ? C12 C13 H13 125.9 . . ? C14 C13 H13 125.9 . . ? N3 C14 C15 124.25(10) . . ? N3 C14 C13 107.07(10) . . ? C15 C14 C13 128.68(10) . . ? C14 C15 C16 122.59(10) . . ? C14 C15 C27 118.10(10) . . ? C16 C15 C27 119.30(10) . . ? N4 C16 C15 124.56(10) . . ? N4 C16 C17 110.42(10) . . ? C15 C16 C17 125.00(10) . . ? C18 C17 C16 106.36(10) . . ? C18 C17 H17 126.8 . . ? C16 C17 H17 126.8 . . ? C17 C18 C19 106.71(10) . . ? C17 C18 H18 126.6 . . ? C19 C18 H18 126.6 . . ? N4 C19 C20 126.72(10) . . ? N4 C19 C18 110.68(10) . . ? C20 C19 C18 122.49(10) . . ? C1 C20 C19 128.83(11) . . ? C1 C20 H20 115.6 . . ? C19 C20 H20 115.6 . . ? C22 C21 C26 118.58(11) . . ? C22 C21 C5 119.39(10) . . ? C26 C21 C5 122.02(11) . . ? C23 C22 C21 120.90(12) . . ? C23 C22 H22 119.5 . . ? C21 C22 H22 119.5 . . ? C24 C23 C22 119.91(12) . . ? C24 C23 H23 120.0 . . ? C22 C23 H23 120.0 . . ? C25 C24 C23 119.97(12) . . ? C25 C24 H24 120.0 . . ? C23 C24 H24 120.0 . . ? C24 C25 C26 120.41(12) . . ? C24 C25 H25 119.8 . . ? C26 C25 H25 119.8 . . ? C25 C26 C21 120.21(12) . . ? C25 C26 H26 119.9 . . ? C21 C26 H26 119.9 . . ? C28 C27 C32 118.19(11) . . ? C28 C27 C15 121.91(10) . . ? C32 C27 C15 119.88(10) . . ? C29 C28 C27 120.77(12) . . ? C29 C28 H28 119.6 . . ? C27 C28 H28 119.6 . . ? C28 C29 C30 120.30(12) . . ? C28 C29 H29 119.9 . . ? C30 C29 H29 119.9 . . ? C31 C30 C29 119.67(11) . . ? C31 C30 H30 120.2 . . ? C29 C30 H30 120.2 . . ? C30 C31 C32 120.20(12) . . ? C30 C31 H31 119.9 . . ? C32 C31 H31 119.9 . . ? C31 C32 C27 120.82(11) . . ? C31 C32 H32 119.6 . . ? C27 C32 H32 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 C4 N1 C1 C20 -179.11(12) . . . . ? C4 N1 C1 C2 1.18(13) . . . . ? N1 C1 C2 C3 -0.33(14) . . . . ? C20 C1 C2 C3 179.94(12) . . . . ? C1 C2 C3 C4 -0.59(15) . . . . ? C1 N1 C4 C5 176.91(11) . . . . ? C1 N1 C4 C3 -1.53(13) . . . . ? C2 C3 C4 N1 1.30(14) . . . . ? C2 C3 C4 C5 -177.07(12) . . . . ? N1 C4 C5 C6 2.50(19) . . . . ? C3 C4 C5 C6 -179.39(12) . . . . ? N1 C4 C5 C21 -171.76(11) . . . . ? C3 C4 C5 C21 6.35(19) . . . . ? C9 N2 C6 C5 -175.11(11) . . . . ? C9 N2 C6 C7 0.69(13) . . . . ? C4 C5 C6 N2 0.25(19) . . . . ? C21 C5 C6 N2 174.44(10) . . . . ? C4 C5 C6 C7 -174.94(11) . . . . ? C21 C5 C6 C7 -0.74(18) . . . . ? N2 C6 C7 C8 -0.10(14) . . . . ? C5 C6 C7 C8 175.67(12) . . . . ? C6 C7 C8 C9 -0.50(14) . . . . ? C6 N2 C9 C10 178.86(12) . . . . ? C6 N2 C9 C8 -1.02(13) . . . . ? C7 C8 C9 N2 0.98(15) . . . . ? C7 C8 C9 C10 -178.91(12) . . . . ? N2 C9 C10 C11 1.0(2) . . . . ? C8 C9 C10 C11 -179.14(13) . . . . ? C14 N3 C11 C10 175.66(12) . . . . ? C14 N3 C11 C12 -1.04(13) . . . . ? C9 C10 C11 N3 -2.7(2) . . . . ? C9 C10 C11 C12 173.48(12) . . . . ? N3 C11 C12 C13 1.52(14) . . . . ? C10 C11 C12 C13 -175.27(12) . . . . ? C11 C12 C13 C14 -1.40(14) . . . . ? C11 N3 C14 C15 -179.76(11) . . . . ? C11 N3 C14 C13 0.19(13) . . . . ? C12 C13 C14 N3 0.78(13) . . . . ? C12 C13 C14 C15 -179.28(12) . . . . ? N3 C14 C15 C16 -5.87(18) . . . . ? C13 C14 C15 C16 174.20(11) . . . . ? N3 C14 C15 C27 172.88(10) . . . . ? C13 C14 C15 C27 -7.05(18) . . . . ? C19 N4 C16 C15 -179.42(11) . . . . ? C19 N4 C16 C17 -1.19(13) . . . . ? C14 C15 C16 N4 7.12(18) . . . . ? C27 C15 C16 N4 -171.61(10) . . . . ? C14 C15 C16 C17 -170.85(11) . . . . ? C27 C15 C16 C17 10.42(17) . . . . ? N4 C16 C17 C18 0.29(14) . . . . ? C15 C16 C17 C18 178.51(11) . . . . ? C16 C17 C18 C19 0.69(13) . . . . ? C16 N4 C19 C20 -174.71(12) . . . . ? C16 N4 C19 C18 1.63(13) . . . . ? C17 C18 C19 N4 -1.49(14) . . . . ? C17 C18 C19 C20 175.04(11) . . . . ? N1 C1 C20 C19 -4.0(2) . . . . ? C2 C1 C20 C19 175.62(12) . . . . ? N4 C19 C20 C1 0.1(2) . . . . ? C18 C19 C20 C1 -175.83(12) . . . . ? C4 C5 C21 C22 52.94(15) . . . . ? C6 C5 C21 C22 -121.54(12) . . . . ? C4 C5 C21 C26 -128.60(12) . . . . ? C6 C5 C21 C26 56.93(16) . . . . ? C26 C21 C22 C23 0.50(18) . . . . ? C5 C21 C22 C23 179.02(11) . . . . ? C21 C22 C23 C24 -1.58(19) . . . . ? C22 C23 C24 C25 1.43(19) . . . . ? C23 C24 C25 C26 -0.21(19) . . . . ? C24 C25 C26 C21 -0.87(19) . . . . ? C22 C21 C26 C25 0.72(18) . . . . ? C5 C21 C26 C25 -177.76(11) . . . . ? C14 C15 C27 C28 52.73(15) . . . . ? C16 C15 C27 C28 -128.48(12) . . . . ? C14 C15 C27 C32 -125.64(12) . . . . ? C16 C15 C27 C32 53.15(15) . . . . ? C32 C27 C28 C29 1.69(17) . . . . ? C15 C27 C28 C29 -176.71(11) . . . . ? C27 C28 C29 C30 -2.48(18) . . . . ? C28 C29 C30 C31 1.21(19) . . . . ? C29 C30 C31 C32 0.79(19) . . . . ? C30 C31 C32 C27 -1.57(18) . . . . ? C28 C27 C32 C31 0.32(17) . . . . ? C15 C27 C32 C31 178.75(11) . . . . ? #===END