# Supplementary Material (ESI) for Green Chemistry # This journal is © The Royal Society of Chemistry 2007 data_global _journal_name_full 'Green Chemistry' _journal_coden_cambridge 1048 _publ_section_title 'On the quantitative recycling of Raney-Nickel catalysts' _publ_contact_author_name 'Axel Jacobi von Wangelin' _publ_contact_author_email AXEL.JACOBI@UNI-KOELN.DE loop_ _publ_author_name 'Waldemar M. Czaplik' 'Jorg M. Neudorfl' 'A.J.von Wangelin' data_z1 _database_code_depnum_ccdc_archive 'CCDC 647735' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H20 N2' _chemical_formula_sum 'C14 H20 N2' _chemical_formula_weight 216.32 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.952(2) _cell_length_b 10.126(3) _cell_length_c 14.757(4) _cell_angle_alpha 70.511(10) _cell_angle_beta 79.526(10) _cell_angle_gamma 76.960(10) _cell_volume 1220.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4976 _cell_measurement_theta_min 1.47 _cell_measurement_theta_max 25.00 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max .2 _exptl_crystal_size_mid .1 _exptl_crystal_size_min .05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.178 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Nonius KappaCCD' _diffrn_measurement_method Phi/Omega-Scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4976 _diffrn_reflns_av_R_equivalents 0.0556 _diffrn_reflns_av_sigmaI/netI 0.1688 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.47 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4031 _reflns_number_gt 1380 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_data_reduction 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL99 (E. Keller 1999)' _computing_publication_material 'PLATON (A. L. Spek 1980-2004)' _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^)+(0.1241P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4031 _refine_ls_number_parameters 309 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2461 _refine_ls_R_factor_gt 0.0879 _refine_ls_wR_factor_ref 0.2937 _refine_ls_wR_factor_gt 0.2204 _refine_ls_goodness_of_fit_ref 0.978 _refine_ls_restrained_S_all 0.978 _refine_ls_shift/su_max 0.013 _refine_ls_shift/su_mean 0.002 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 0.8660(6) 0.8683(6) 0.5050(4) 0.0494(14) Uani 1 1 d . . . N2 N 0.6485(5) 1.0584(6) 0.5704(3) 0.0469(13) Uani 1 1 d . . . C3 C 0.6880(6) 1.0906(6) 0.4691(3) 0.0397(14) Uani 1 1 d . . . C4 C 0.8522(6) 1.0173(6) 0.3371(4) 0.0433(14) Uani 1 1 d . . . C5 C 0.8054(6) 0.9936(6) 0.4356(4) 0.0394(14) Uani 1 1 d . . . N6 N 0.6973(6) 1.3646(6) 0.0042(4) 0.0518(14) Uani 1 1 d . . . C7 C 0.6218(6) 1.2167(6) 0.4057(4) 0.0466(15) Uani 1 1 d . . . C8 C 0.7753(6) 1.5904(6) -0.0298(4) 0.0459(15) Uani 1 1 d . . . N9 N 0.7833(6) 1.5519(6) 0.0710(3) 0.0500(14) Uani 1 1 d . . . C10 C 0.7254(5) 1.4961(6) -0.0638(4) 0.0443(14) Uani 1 1 d . . . C11 C 0.8053(6) 1.7214(6) -0.0925(4) 0.0510(15) Uani 1 1 d . . . C12 C 0.7136(6) 1.5250(6) -0.1619(4) 0.0472(15) Uani 1 1 d . . . C13 C 0.5022(6) 1.3227(6) 0.4414(4) 0.0544(16) Uani 1 1 d . . . H13A H 0.5299 1.4184 0.4110 0.065 Uiso 1 1 calc R . . H13B H 0.4014 1.3253 0.4216 0.065 Uiso 1 1 calc R . . C14 C 0.9689(6) 0.9100(6) 0.3011(4) 0.0522(16) Uani 1 1 d . . . H14A H 0.9311 0.8935 0.2475 0.063 Uiso 1 1 calc R . . H14B H 1.0664 0.9473 0.2755 0.063 Uiso 1 1 calc R . . C15 C 1.0400(6) 0.6429(6) 0.5540(4) 0.0582(16) Uani 1 1 d . . . H15A H 0.9528 0.5917 0.5757 0.087 Uiso 1 1 calc R . . H15B H 1.0633 0.6681 0.6078 0.087 Uiso 1 1 calc R . . H15C H 1.1306 0.5820 0.5315 0.087 Uiso 1 1 calc R . . C16 C 0.7831(6) 1.1437(7) 0.2732(4) 0.0572(17) Uani 1 1 d . . . H16 H 0.8128 1.1626 0.2055 0.069 Uiso 1 1 calc R . . C17 C 0.9992(8) 0.7753(7) 0.4729(4) 0.078(2) Uani 1 1 d . . . H17 H 1.0855 0.8272 0.4655 0.093 Uiso 1 1 calc R . . C18 C 0.5219(8) 1.1525(8) 0.6063(4) 0.090(2) Uani 1 1 d . . . H18 H 0.4337 1.1137 0.5980 0.108 Uiso 1 1 calc R . . C19 C 0.8512(7) 1.8251(6) -0.0551(4) 0.0610(17) Uani 1 1 d . . . H19A H 0.9556 1.8425 -0.0861 0.073 Uiso 1 1 calc R . . H19B H 0.7786 1.9168 -0.0731 0.073 Uiso 1 1 calc R . . C20 C 0.6732(6) 1.2409(6) 0.3064(4) 0.0561(17) Uani 1 1 d . . . H20 H 0.6308 1.3269 0.2611 0.067 Uiso 1 1 calc R . . C21 C 0.7902(6) 1.7503(6) -0.1907(4) 0.0587(17) Uani 1 1 d . . . H21 H 0.8101 1.8387 -0.2354 0.070 Uiso 1 1 calc R . . C22 C 0.6711(6) 1.4185(6) -0.1984(4) 0.0566(17) Uani 1 1 d . . . H22A H 0.5636 1.4505 -0.2148 0.068 Uiso 1 1 calc R . . H22B H 0.7396 1.4126 -0.2582 0.068 Uiso 1 1 calc R . . C23 C 0.4874(8) 1.2890(8) 0.5461(5) 0.092(2) Uani 1 1 d . . . H23A H 0.5522 1.3456 0.5601 0.110 Uiso 1 1 calc R . . H23B H 0.3790 1.3263 0.5668 0.110 Uiso 1 1 calc R . . C24 C 0.6290(8) 1.2742(7) -0.0282(4) 0.0696(19) Uani 1 1 d . . . H24 H 0.5186 1.3222 -0.0313 0.083 Uiso 1 1 calc R . . C25 C 0.6213(7) 1.1365(6) 0.0501(4) 0.0667(18) Uani 1 1 d . . . H25A H 0.7260 1.0823 0.0589 0.100 Uiso 1 1 calc R . . H25B H 0.5608 1.0814 0.0322 0.100 Uiso 1 1 calc R . . H25C H 0.5720 1.1552 0.1106 0.100 Uiso 1 1 calc R . . C26 C 0.5042(6) 1.1121(6) 0.7127(4) 0.0649(18) Uani 1 1 d . . . H26A H 0.5916 1.1329 0.7338 0.097 Uiso 1 1 calc R . . H26B H 0.5013 1.0101 0.7399 0.097 Uiso 1 1 calc R . . H26C H 0.4079 1.1664 0.7353 0.097 Uiso 1 1 calc R . . C27 C 0.9991(9) 0.7731(8) 0.3795(5) 0.104(3) Uani 1 1 d . . . H27A H 0.9208 0.7166 0.3816 0.124 Uiso 1 1 calc R . . H27B H 1.1008 0.7206 0.3605 0.124 Uiso 1 1 calc R . . C28 C 0.7479(6) 1.6552(7) -0.2237(4) 0.0599(17) Uani 1 1 d . . . H28 H 0.7417 1.6782 -0.2910 0.072 Uiso 1 1 calc R . . C29 C 0.8516(11) 1.7743(7) 0.0502(5) 0.128(4) Uani 1 1 d . . . H29A H 0.9503 1.7904 0.0623 0.153 Uiso 1 1 calc R . . H29B H 0.7689 1.8403 0.0757 0.153 Uiso 1 1 calc R . . C30 C 0.8362(11) 1.6481(10) 0.1054(5) 0.117(3) Uani 1 1 d . . . H30 H 0.9473 1.6080 0.0905 0.141 Uiso 1 1 calc R . . C31 C 0.8429(6) 1.5908(6) 0.2121(4) 0.0643(18) Uani 1 1 d . . . H31A H 0.9005 1.6465 0.2316 0.096 Uiso 1 1 calc R . . H31B H 0.8948 1.4910 0.2289 0.096 Uiso 1 1 calc R . . H31C H 0.7379 1.5971 0.2459 0.096 Uiso 1 1 calc R . . C32 C 0.6848(8) 1.2773(7) -0.1262(5) 0.086(2) Uani 1 1 d . . . H32A H 0.6280 1.2188 -0.1448 0.103 Uiso 1 1 calc R . . H32B H 0.7950 1.2317 -0.1286 0.103 Uiso 1 1 calc R . . H1 H 0.872(6) 0.876(6) 0.552(4) 0.043(19) Uiso 1 1 d . . . H2 H 0.659(6) 1.389(6) 0.050(4) 0.07(2) Uiso 1 1 d . . . H5 H 0.631(6) 0.974(6) 0.591(4) 0.08(2) Uiso 1 1 d . . . H6 H 0.827(6) 1.466(6) 0.089(4) 0.07(2) Uiso 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 N1 0.063(3) 0.048(4) 0.032(3) -0.010(3) -0.001(3) -0.008(3) N2 0.061(3) 0.040(4) 0.033(3) -0.009(3) 0.003(2) -0.006(3) C3 0.055(4) 0.039(4) 0.023(3) -0.007(3) 0.000(3) -0.012(3) C4 0.054(3) 0.044(4) 0.031(3) -0.009(3) -0.001(3) -0.014(3) C5 0.048(3) 0.037(4) 0.029(3) -0.005(3) -0.003(3) -0.009(3) N6 0.070(3) 0.052(4) 0.039(3) -0.022(3) -0.003(3) -0.012(3) C7 0.055(4) 0.050(4) 0.028(3) -0.006(3) -0.003(3) -0.007(3) C8 0.051(4) 0.051(4) 0.033(4) -0.014(3) -0.002(3) -0.003(3) N9 0.067(3) 0.048(4) 0.036(3) -0.016(3) -0.003(2) -0.010(3) C10 0.048(3) 0.045(4) 0.032(3) -0.007(3) 0.000(3) -0.006(3) C11 0.061(4) 0.049(4) 0.037(4) -0.010(3) 0.005(3) -0.014(3) C12 0.051(3) 0.057(4) 0.032(3) -0.014(3) -0.004(3) -0.008(3) C13 0.061(4) 0.054(4) 0.044(4) -0.012(3) -0.003(3) -0.008(3) C14 0.063(4) 0.047(4) 0.042(4) -0.010(3) -0.002(3) -0.010(3) C15 0.070(4) 0.042(4) 0.055(4) -0.009(3) -0.005(3) -0.003(3) C16 0.067(4) 0.063(5) 0.035(4) -0.007(4) -0.005(3) -0.012(4) C17 0.087(5) 0.066(5) 0.050(4) -0.007(4) 0.004(4) 0.021(4) C18 0.114(6) 0.085(6) 0.037(4) -0.017(4) 0.010(4) 0.031(5) C19 0.067(4) 0.064(5) 0.050(4) -0.016(4) 0.011(3) -0.024(3) C20 0.062(4) 0.051(4) 0.044(4) 0.000(3) -0.013(3) -0.005(3) C21 0.080(4) 0.049(4) 0.038(4) -0.007(3) 0.008(3) -0.013(4) C22 0.064(4) 0.069(5) 0.035(3) -0.017(4) -0.002(3) -0.010(3) C23 0.121(6) 0.067(5) 0.053(5) -0.011(4) 0.001(4) 0.031(5) C24 0.106(5) 0.063(5) 0.045(4) -0.010(4) 0.002(4) -0.044(4) C25 0.093(5) 0.051(4) 0.060(4) -0.016(4) -0.009(4) -0.021(4) C26 0.080(4) 0.063(5) 0.044(4) -0.018(3) 0.008(3) -0.008(4) C27 0.145(7) 0.090(6) 0.048(5) -0.029(5) -0.010(4) 0.047(5) C28 0.073(4) 0.069(5) 0.032(4) -0.013(4) -0.001(3) -0.009(4) C29 0.277(11) 0.040(5) 0.084(6) 0.015(4) -0.102(7) -0.050(6) C30 0.218(9) 0.131(8) 0.038(4) -0.025(5) 0.002(5) -0.118(7) C31 0.081(4) 0.059(4) 0.057(4) -0.022(4) -0.024(3) -0.002(3) C32 0.132(6) 0.078(6) 0.058(5) -0.021(4) -0.029(4) -0.025(5) _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 C5 1.407(7) . ? N1 C17 1.455(7) . ? N1 H1 0.74(4) . ? N2 C3 1.415(6) . ? N2 C18 1.450(7) . ? N2 H5 0.84(6) . ? C3 C7 1.385(7) . ? C3 C5 1.408(7) . ? C4 C5 1.392(7) . ? C4 C16 1.400(7) . ? C4 C14 1.492(7) . ? N6 C10 1.417(7) . ? N6 C24 1.446(7) . ? N6 H2 0.79(5) . ? C7 C20 1.410(7) . ? C7 C13 1.493(7) . ? C8 C11 1.392(7) . ? C8 C10 1.399(7) . ? C8 N9 1.417(6) . ? N9 C30 1.435(7) . ? N9 H6 0.84(5) . ? C10 C12 1.396(6) . ? C11 C21 1.406(7) . ? C11 C19 1.497(7) . ? C12 C28 1.394(7) . ? C12 C22 1.499(7) . ? C13 C23 1.454(7) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C27 1.486(7) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C17 1.493(7) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C20 1.373(7) . ? C16 H16 0.9500 . ? C17 C27 1.386(8) . ? C17 H17 1.0000 . ? C18 C23 1.372(8) . ? C18 C26 1.473(7) . ? C18 H18 1.0000 . ? C19 C29 1.464(8) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 H20 0.9500 . ? C21 C28 1.361(7) . ? C21 H21 0.9500 . ? C22 C32 1.465(7) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C32 1.434(8) . ? C24 C25 1.492(7) . ? C24 H24 1.0000 . ? 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 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 H28 0.9500 . ? C29 C30 1.288(8) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 C31 1.493(8) . ? C30 H30 1.0000 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? 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 C5 N1 C17 117.8(5) . . ? C5 N1 H1 115(4) . . ? C17 N1 H1 113(4) . . ? C3 N2 C18 118.0(5) . . ? C3 N2 H5 106(4) . . ? C18 N2 H5 111(4) . . ? C7 C3 C5 121.2(5) . . ? C7 C3 N2 121.6(5) . . ? C5 C3 N2 117.1(5) . . ? C5 C4 C16 117.5(5) . . ? C5 C4 C14 121.1(5) . . ? C16 C4 C14 121.4(5) . . ? C4 C5 N1 121.5(6) . . ? C4 C5 C3 121.0(5) . . ? N1 C5 C3 117.4(5) . . ? C10 N6 C24 117.4(5) . . ? C10 N6 H2 101(4) . . ? C24 N6 H2 121(4) . . ? C3 C7 C20 117.1(5) . . ? C3 C7 C13 121.3(5) . . ? C20 C7 C13 121.6(5) . . ? C11 C8 C10 120.6(5) . . ? C11 C8 N9 121.7(5) . . ? C10 C8 N9 117.6(5) . . ? C8 N9 C30 117.4(5) . . ? C8 N9 H6 108(4) . . ? C30 N9 H6 116(4) . . ? C12 C10 C8 121.7(5) . . ? C12 C10 N6 120.8(6) . . ? C8 C10 N6 117.4(5) . . ? C8 C11 C21 117.0(5) . . ? C8 C11 C19 120.5(5) . . ? C21 C11 C19 122.5(6) . . ? C28 C12 C10 116.7(5) . . ? C28 C12 C22 122.1(5) . . ? C10 C12 C22 121.2(5) . . ? C23 C13 C7 112.2(5) . . ? C23 C13 H13A 109.2 . . ? C7 C13 H13A 109.2 . . ? C23 C13 H13B 109.2 . . ? C7 C13 H13B 109.2 . . ? H13A C13 H13B 107.9 . . ? C27 C14 C4 111.1(5) . . ? C27 C14 H14A 109.4 . . ? C4 C14 H14A 109.4 . . ? C27 C14 H14B 109.4 . . ? C4 C14 H14B 109.4 . . ? H14A C14 H14B 108.0 . . ? C17 C15 H15A 109.5 . . ? C17 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C17 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C20 C16 C4 121.3(5) . . ? C20 C16 H16 119.4 . . ? C4 C16 H16 119.4 . . ? C27 C17 N1 113.5(6) . . ? C27 C17 C15 122.3(6) . . ? N1 C17 C15 110.4(5) . . ? C27 C17 H17 102.5 . . ? N1 C17 H17 102.5 . . ? C15 C17 H17 102.5 . . ? C23 C18 N2 116.7(6) . . ? C23 C18 C26 124.7(6) . . ? N2 C18 C26 111.4(5) . . ? C23 C18 H18 99.0 . . ? N2 C18 H18 99.0 . . ? C26 C18 H18 99.0 . . ? C29 C19 C11 112.5(5) . . ? C29 C19 H19A 109.1 . . ? C11 C19 H19A 109.1 . . ? C29 C19 H19B 109.1 . . ? C11 C19 H19B 109.1 . . ? H19A C19 H19B 107.8 . . ? C16 C20 C7 121.8(5) . . ? C16 C20 H20 119.1 . . ? C7 C20 H20 119.1 . . ? C28 C21 C11 121.9(6) . . ? C28 C21 H21 119.1 . . ? C11 C21 H21 119.1 . . ? C32 C22 C12 111.4(5) . . ? C32 C22 H22A 109.4 . . ? C12 C22 H22A 109.4 . . ? C32 C22 H22B 109.4 . . ? C12 C22 H22B 109.4 . . ? H22A C22 H22B 108.0 . . ? C18 C23 C13 122.5(6) . . ? C18 C23 H23A 106.7 . . ? C13 C23 H23A 106.7 . . ? C18 C23 H23B 106.7 . . ? C13 C23 H23B 106.7 . . ? H23A C23 H23B 106.6 . . ? C32 C24 N6 112.8(5) . . ? C32 C24 C25 120.9(6) . . ? N6 C24 C25 109.5(5) . . ? C32 C24 H24 103.9 . . ? N6 C24 H24 103.9 . . ? C25 C24 H24 103.9 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C18 C26 H26A 109.5 . . ? C18 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C18 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C17 C27 C14 119.2(6) . . ? C17 C27 H27A 107.5 . . ? C14 C27 H27A 107.5 . . ? C17 C27 H27B 107.5 . . ? C14 C27 H27B 107.5 . . ? H27A C27 H27B 107.0 . . ? C21 C28 C12 122.0(5) . . ? C21 C28 H28 119.0 . . ? C12 C28 H28 119.0 . . ? C30 C29 C19 125.6(6) . . ? C30 C29 H29A 105.9 . . ? C19 C29 H29A 105.9 . . ? C30 C29 H29B 105.9 . . ? C19 C29 H29B 105.9 . . ? H29A C29 H29B 106.2 . . ? C29 C30 N9 121.2(6) . . ? C29 C30 C31 127.0(6) . . ? N9 C30 C31 111.0(6) . . ? C29 C30 H30 92.9 . . ? N9 C30 H30 92.9 . . ? C31 C30 H30 92.9 . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C24 C32 C22 116.0(6) . . ? C24 C32 H32A 108.3 . . ? C22 C32 H32A 108.3 . . ? C24 C32 H32B 108.3 . . ? C22 C32 H32B 108.3 . . ? H32A C32 H32B 107.4 . . ? _diffrn_measured_fraction_theta_max 0.939 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.939 _refine_diff_density_max 0.269 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.054