Supplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Alan Cowley' 'Dario Braga' 'Silvia Filipponi' 'Fabrizia Grepioni' 'Jennifer A. Johnson' 'Jamie N. Jones' _publ_contact_author_name 'Dr Alan Cowley' _publ_contact_author_address ; Chemistry & Biochemistry University of Texas at Austin 1 University Station A5300 Austin TX 78712-0165 UNITED STATES OF AMERICA ; _publ_contact_author_email COWLEY@MAIL.UTEXAS.EDU _publ_requested_journal 'Chemical Communications' _publ_section_title ; Isolation of C-H...C(pi) complexes from the reaction of stable carbenes with hydrocarbons ; data_pnma _database_code_CSD 220953 _audit_creation_method SHELXL-97 _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '[C9 H13][C13 H9]' _chemical_formula_sum 'C10 H11 N' _chemical_formula_weight 145.20 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 Orthorhombic _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-x, y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z-1/2' 'x, -y-1/2, z' _cell_length_a 12.162(5) _cell_length_b 17.397(5) _cell_length_c 7.375(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 90.000(5) _cell_angle_gamma 90.000(5) _cell_volume 1560.4(13) _cell_formula_units_Z 8 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used all _cell_measurement_theta_min 3.00 _cell_measurement_theta_max 27.44 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.236 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9856 _exptl_absorpt_correction_T_max 0.9856 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5743 _diffrn_reflns_av_R_equivalents 0.0368 _diffrn_reflns_av_sigmaI/netI 0.0419 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 27.44 _reflns_number_total 1844 _reflns_number_gt 1370 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement DENZO _computing_data_reduction Scalepack _computing_structure_solution 'WinGX (Farrugia, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _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. ; _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^)+(0.0501P)^2^+0.4131P] 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 SHELXL _refine_ls_extinction_coef 0.013(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1844 _refine_ls_number_parameters 150 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0725 _refine_ls_R_factor_gt 0.0456 _refine_ls_wR_factor_ref 0.1091 _refine_ls_wR_factor_gt 0.0985 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.002 _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 C1 C 0.31137(10) 0.20869(7) 0.12127(16) 0.0199(3) Uani 1 1 d . . . C2 C 0.21480(11) 0.18440(7) 0.22073(16) 0.0210(3) Uani 1 1 d . . . C3 C 0.19454(12) 0.10433(8) 0.23852(18) 0.0251(3) Uani 1 1 d . . . C4 C 0.26642(12) 0.05232(8) 0.16256(19) 0.0290(4) Uani 1 1 d . . . C5 C 0.36101(12) 0.07660(8) 0.06769(19) 0.0285(4) Uani 1 1 d . . . C6 C 0.38327(11) 0.15418(8) 0.04827(18) 0.0237(3) Uani 1 1 d . . . C7 C 0.15738(16) 0.2500 0.2825(2) 0.0231(4) Uani 1 2 d S . . C8 C 0.92427(17) 0.2500 0.9792(3) 0.0241(4) Uani 1 2 d S . . C9 C 1.07015(11) 0.21101(8) 0.82396(16) 0.0215(3) Uani 1 1 d . . . C10 C 0.94529(14) 0.10869(9) 0.9576(2) 0.0318(4) Uani 1 1 d . . . C11 C 1.14792(13) 0.15476(9) 0.7439(2) 0.0283(4) Uani 1 1 d . . . N1 N 0.97791(9) 0.18810(6) 0.92183(14) 0.0232(3) Uani 1 1 d . . . H3 H 0.1278(12) 0.0867(8) 0.3087(19) 0.025(4) Uiso 1 1 d . . . H4 H 0.2515(13) -0.0038(10) 0.1798(19) 0.036(4) Uiso 1 1 d . . . H5 H 0.4124(14) 0.0371(9) 0.015(2) 0.043(5) Uiso 1 1 d . . . H6 H 0.4534(12) 0.1720(9) -0.017(2) 0.031(4) Uiso 1 1 d . . . H7 H 0.0862(19) 0.2500 0.350(3) 0.034(6) Uiso 1 2 d S . . H8 H 0.856(2) 0.2500 1.049(3) 0.039(6) Uiso 1 2 d S . . H10A H 0.8799(15) 0.1091(9) 1.039(2) 0.042(5) Uiso 1 1 d . . . H10B H 0.9244(14) 0.0830(10) 0.842(3) 0.053(5) Uiso 1 1 d . . . H10C H 1.0108(17) 0.0796(10) 1.011(2) 0.057(5) Uiso 1 1 d . . . H11A H 1.1087(15) 0.1138(11) 0.671(3) 0.056(5) Uiso 1 1 d . . . H11B H 1.1922(14) 0.1284(10) 0.834(2) 0.048(5) Uiso 1 1 d . . . H11C H 1.1982(16) 0.1819(11) 0.666(3) 0.060(6) 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 C1 0.0206(7) 0.0215(7) 0.0176(6) 0.0000(5) -0.0031(5) -0.0010(5) C2 0.0221(7) 0.0228(7) 0.0182(6) 0.0000(5) -0.0022(5) -0.0013(5) C3 0.0258(8) 0.0251(7) 0.0245(7) 0.0022(6) -0.0031(6) -0.0042(6) C4 0.0344(9) 0.0197(7) 0.0329(7) 0.0002(6) -0.0084(6) -0.0024(6) C5 0.0293(8) 0.0254(7) 0.0308(7) -0.0059(6) -0.0056(6) 0.0056(6) C6 0.0223(7) 0.0270(7) 0.0220(7) -0.0019(6) -0.0015(6) 0.0011(6) C7 0.0218(10) 0.0259(10) 0.0217(9) 0.000 0.0024(8) 0.000 C8 0.0230(10) 0.0295(11) 0.0199(9) 0.000 0.0008(8) 0.000 C9 0.0204(7) 0.0268(7) 0.0172(6) 0.0015(5) -0.0013(5) -0.0012(5) C10 0.0360(9) 0.0266(8) 0.0328(8) 0.0036(6) 0.0016(7) -0.0086(7) C11 0.0296(8) 0.0285(8) 0.0269(8) -0.0020(6) 0.0000(6) 0.0066(7) N1 0.0238(6) 0.0255(6) 0.0203(5) 0.0005(4) -0.0010(5) -0.0024(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 C1 C6 1.3977(19) . ? C1 C1 1.437(3) 8_565 ? C1 C2 1.4478(19) . ? C2 C7 1.4133(17) . ? C2 C3 1.4208(19) . ? C3 C4 1.377(2) . ? C4 C5 1.411(2) . ? C5 C6 1.384(2) . ? C7 C2 1.4133(17) 8_565 ? C8 N1 1.3283(16) . ? C8 N1 1.3283(16) 8_565 ? C9 C9 1.357(3) 8_565 ? C9 N1 1.3923(17) . ? C9 C11 1.4833(19) . ? C10 N1 1.4613(19) . ? 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 C6 C1 C1 132.72(8) . 8_565 ? C6 C1 C2 120.31(12) . . ? C1 C1 C2 106.97(7) 8_565 . ? C7 C2 C3 132.56(13) . . ? C7 C2 C1 109.17(12) . . ? C3 C2 C1 118.27(12) . . ? C4 C3 C2 119.77(13) . . ? C3 C4 C5 121.50(14) . . ? C6 C5 C4 120.18(13) . . ? C5 C6 C1 119.96(13) . . ? C2 C7 C2 107.70(17) . 8_565 ? N1 C8 N1 108.34(17) . 8_565 ? C9 C9 N1 106.63(7) 8_565 . ? C9 C9 C11 131.27(8) 8_565 . ? N1 C9 C11 122.09(13) . . ? C8 N1 C9 109.20(12) . . ? C8 N1 C10 125.15(13) . . ? C9 N1 C10 125.65(12) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.44 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.281 _refine_diff_density_min -0.176 _refine_diff_density_rms 0.042 data_p1 _database_code_CSD 220954 _audit_creation_method SHELXL-97 _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11.50 H16 N2' _chemical_formula_weight 182.26 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 P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 8.0705(16) _cell_length_b 8.4239(17) _cell_length_c 8.6894(17) _cell_angle_alpha 77.92(3) _cell_angle_beta 64.47(3) _cell_angle_gamma 79.29(3) _cell_volume 518.19(18) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used all _cell_measurement_theta_min 2.96 _cell_measurement_theta_max 27.52 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.168 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 198 _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9861 _exptl_absorpt_correction_T_max 0.9861 _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 'Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3530 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0684 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 27.52 _reflns_number_total 3530 _reflns_number_gt 2660 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement DENZO _computing_data_reduction Scalepack _computing_structure_solution 'WinGX (Farrugia, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _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. ; _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^)+(0.0595P)^2^+0.2225P] 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 SHELXL _refine_ls_extinction_coef 0.135(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 5(4) _refine_ls_number_reflns 3530 _refine_ls_number_parameters 369 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0886 _refine_ls_R_factor_gt 0.0584 _refine_ls_wR_factor_ref 0.1434 _refine_ls_wR_factor_gt 0.1273 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.028 _refine_ls_shift/su_mean 0.005 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 C17 C 0.0171(5) 0.5189(4) 0.1840(5) 0.0370(8) Uani 1 1 d . . . C20 C -0.2717(6) 0.6906(5) 0.3142(6) 0.0492(10) Uani 1 1 d . . . C23 C 0.1888(6) 0.2700(6) 0.0750(5) 0.0456(9) Uani 1 1 d . . . N3 N -0.1470(4) 0.5501(3) 0.3430(4) 0.0392(7) Uani 1 1 d . . . N4 N 0.0793(4) 0.3459(3) 0.2293(3) 0.0381(7) Uani 1 1 d . . . H1 H 0.528(7) 0.575(7) 0.021(7) 0.082(15) Uiso 1 1 d . . . H4A H 0.400(8) 0.345(7) 0.235(6) 0.080(15) Uiso 1 1 d . . . H4B H 0.579(7) 0.260(6) 0.283(6) 0.066(14) Uiso 1 1 d . . . H4C H 0.508(6) 0.156(6) 0.178(5) 0.055(12) Uiso 1 1 d . . . H5A H 0.862(6) 0.052(5) 0.083(6) 0.049(11) Uiso 1 1 d . . . H5B H 0.768(8) 0.009(6) -0.027(7) 0.082(15) Uiso 1 1 d . . . H5C H 1.003(8) 0.054(7) -0.132(7) 0.087(16) Uiso 1 1 d . . . H6A H 1.061(5) 0.383(5) -0.466(6) 0.045(10) Uiso 1 1 d . . . H6B H 1.142(5) 0.446(5) -0.356(5) 0.043(11) Uiso 1 1 d . . . H6C H 1.129(7) 0.244(7) -0.343(6) 0.075(15) Uiso 1 1 d . . . H7A H 0.689(7) 0.748(6) -0.255(6) 0.076(15) Uiso 1 1 d . . . H7B H 0.893(8) 0.717(7) -0.254(7) 0.094(18) Uiso 1 1 d . . . H7C H 0.847(6) 0.648(6) -0.411(6) 0.066(13) Uiso 1 1 d . . . C1 C 0.6316(5) 0.4900(5) -0.0282(5) 0.0419(9) Uani 1 1 d . . . C2 C 0.8923(5) 0.3687(5) -0.2042(5) 0.0412(9) Uani 1 1 d . . . C3 C 0.8108(5) 0.2547(5) -0.0701(5) 0.0421(9) Uani 1 1 d . . . C4 C 0.5204(6) 0.2607(6) 0.2090(5) 0.0521(11) Uani 1 1 d . . . C5 C 0.8671(7) 0.0767(5) -0.0310(7) 0.0551(11) Uani 1 1 d . . . C6 C 1.0735(6) 0.3571(6) -0.3573(5) 0.0455(10) Uani 1 1 d . . . C7 C 0.8101(6) 0.6726(5) -0.2918(6) 0.0488(10) Uani 1 1 d . . . C8 C 0.2227(5) 0.6932(4) 0.2278(5) 0.0389(8) Uani 1 1 d . . . C9 C 0.3340(5) 0.8198(5) 0.1318(5) 0.0430(9) Uani 1 1 d . . . C10 C 0.3349(5) 0.8462(4) -0.0352(4) 0.0390(8) Uani 1 1 d . . . C11 C 0.4176(5) 0.9612(5) -0.1869(5) 0.0451(9) Uani 1 1 d . . . C12 C 0.3921(5) 0.9583(5) -0.3316(5) 0.0474(10) Uani 1 1 d . . . H12 H 0.4451 1.0357 -0.4308 0.057 Uiso 1 1 calc R . . C13 C 0.2890(5) 0.8435(5) -0.3380(5) 0.0484(10) Uani 1 1 d . . . C14 C 0.2092(5) 0.7300(5) -0.1923(5) 0.0443(9) Uani 1 1 d . . . C15 C 0.2266(4) 0.7309(4) -0.0398(4) 0.0375(8) Uani 1 1 d . . . C16 C 0.1550(5) 0.6376(4) 0.1270(4) 0.0376(8) Uani 1 1 d . . . C18 C -0.0876(5) 0.2770(5) 0.3512(5) 0.0405(9) Uani 1 1 d . . . C19 C -0.2183(5) 0.3951(5) 0.4160(5) 0.0435(9) Uani 1 1 d . . . C21 C -0.4040(6) 0.3867(7) 0.5609(6) 0.0513(11) Uani 1 1 d . . . C22 C -0.0798(7) 0.0963(5) 0.4129(6) 0.0523(11) Uani 1 1 d . . . N1 N 0.6465(4) 0.3324(4) 0.0388(4) 0.0422(8) Uani 1 1 d . . . N2 N 0.7774(4) 0.5147(4) -0.1754(4) 0.0396(7) Uani 1 1 d . . . H8 H 0.206(4) 0.649(4) 0.342(5) 0.023(8) Uiso 1 1 d . . . H9 H 0.400(6) 0.886(5) 0.166(5) 0.048(11) Uiso 1 1 d . . . H11 H 0.506(6) 1.048(6) -0.194(6) 0.059(12) Uiso 1 1 d . . . H13 H 0.272(5) 0.842(4) -0.449(5) 0.036(9) Uiso 1 1 d . . . H14 H 0.133(6) 0.648(5) -0.196(5) 0.046(11) Uiso 1 1 d . . . H17 H -0.015(4) 0.532(3) 0.078(4) 0.017(7) Uiso 1 1 d . . . H20A H -0.309(6) 0.680(5) 0.221(6) 0.060(12) Uiso 1 1 d . . . H20B H -0.385(6) 0.708(5) 0.412(5) 0.047(11) Uiso 1 1 d . . . H20C H -0.210(6) 0.809(6) 0.277(6) 0.063(13) Uiso 1 1 d . . . H21A H -0.491(7) 0.448(6) 0.527(6) 0.062(14) Uiso 1 1 d . . . H21B H -0.409(6) 0.456(6) 0.631(6) 0.061(13) Uiso 1 1 d . . . H21C H -0.412(6) 0.271(6) 0.607(6) 0.054(12) Uiso 1 1 d . . . H22A H 0.026(7) 0.062(6) 0.459(6) 0.064(13) Uiso 1 1 d . . . H22B H -0.029(6) 0.023(5) 0.325(5) 0.048(11) Uiso 1 1 d . . . H22C H -0.200(10) 0.085(8) 0.489(8) 0.11(2) Uiso 1 1 d . . . H23A H 0.131(6) 0.283(5) -0.006(6) 0.054(11) Uiso 1 1 d . . . H23B H 0.205(5) 0.155(5) 0.118(5) 0.048(11) Uiso 1 1 d . . . H23C H 0.308(6) 0.347(5) -0.010(5) 0.049(11) 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 C17 0.0318(19) 0.038(2) 0.0356(18) -0.0084(16) -0.0085(16) 0.0001(16) C20 0.035(2) 0.045(2) 0.055(3) -0.0110(19) -0.010(2) 0.0103(18) C23 0.042(2) 0.044(2) 0.044(2) -0.0168(18) -0.011(2) 0.0034(19) N3 0.0298(15) 0.0373(17) 0.0406(17) -0.0090(13) -0.0058(13) 0.0016(13) N4 0.0290(16) 0.0388(18) 0.0372(16) -0.0077(13) -0.0046(13) -0.0021(13) C1 0.032(2) 0.052(3) 0.037(2) -0.0103(18) -0.0092(17) 0.0002(18) C2 0.0338(19) 0.045(2) 0.041(2) -0.0122(17) -0.0136(17) 0.0067(17) C3 0.037(2) 0.046(2) 0.039(2) -0.0088(17) -0.0131(18) 0.0015(18) C4 0.047(3) 0.065(3) 0.038(2) -0.001(2) -0.012(2) -0.012(2) C5 0.054(3) 0.046(2) 0.056(3) -0.005(2) -0.017(2) -0.001(2) C6 0.040(2) 0.050(3) 0.038(2) -0.0094(19) -0.0091(18) 0.002(2) C7 0.044(2) 0.048(2) 0.047(2) -0.005(2) -0.016(2) 0.002(2) C8 0.0381(19) 0.041(2) 0.0294(19) -0.0094(16) -0.0049(16) -0.0013(17) C9 0.035(2) 0.041(2) 0.048(2) -0.0125(18) -0.0119(17) 0.0020(17) C10 0.0326(18) 0.0319(19) 0.0397(19) -0.0081(15) -0.0052(16) 0.0057(15) C11 0.0319(19) 0.038(2) 0.049(2) -0.0067(17) -0.0035(17) 0.0024(16) C12 0.037(2) 0.047(2) 0.040(2) -0.0033(17) -0.0023(17) 0.0014(18) C13 0.046(2) 0.057(3) 0.030(2) -0.0083(18) -0.0089(18) 0.009(2) C14 0.034(2) 0.046(2) 0.043(2) -0.0117(18) -0.0090(18) 0.0062(18) C15 0.0270(18) 0.0372(19) 0.0365(19) -0.0112(16) -0.0034(15) 0.0070(15) C16 0.0338(19) 0.0347(19) 0.0337(19) -0.0070(15) -0.0045(16) -0.0003(15) C18 0.0306(18) 0.044(2) 0.0396(19) -0.0102(17) -0.0049(16) -0.0069(16) C19 0.036(2) 0.047(2) 0.044(2) -0.0092(18) -0.0110(18) -0.0067(18) C21 0.035(2) 0.057(3) 0.053(3) -0.014(2) -0.005(2) -0.007(2) C22 0.047(3) 0.038(2) 0.062(3) -0.003(2) -0.015(2) -0.006(2) N1 0.0316(16) 0.052(2) 0.0352(17) -0.0078(14) -0.0072(14) -0.0018(14) N2 0.0330(17) 0.0431(18) 0.0368(16) -0.0121(14) -0.0096(14) 0.0051(14) _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 C17 N3 1.476(4) . ? C17 N4 1.479(5) . ? C17 C16 1.489(5) . ? C20 N3 1.459(5) . ? C23 N4 1.454(5) . ? N3 C19 1.433(5) . ? N4 C18 1.441(5) . ? C1 N2 1.321(5) . ? C1 N1 1.339(5) . ? C2 C3 1.348(5) . ? C2 N2 1.393(5) . ? C2 C6 1.498(5) . ? C3 N1 1.392(4) . ? C3 C5 1.495(6) . ? C4 N1 1.464(5) . ? C7 N2 1.483(5) . ? C8 C16 1.402(5) . ? C8 C9 1.407(6) . ? C9 C10 1.419(5) . ? C10 C11 1.438(5) . ? C10 C15 1.439(5) . ? C11 C12 1.365(5) . ? C12 C13 1.411(6) . ? C13 C14 1.397(6) . ? C14 C15 1.392(5) . ? C15 C16 1.422(5) . ? C18 C19 1.324(5) . ? C18 C22 1.504(6) . ? C19 C21 1.487(6) . ? 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 N3 C17 N4 101.8(3) . . ? N3 C17 C16 113.6(3) . . ? N4 C17 C16 116.6(3) . . ? C19 N3 C20 118.4(3) . . ? C19 N3 C17 104.8(3) . . ? C20 N3 C17 112.6(3) . . ? C18 N4 C23 117.6(3) . . ? C18 N4 C17 104.3(3) . . ? C23 N4 C17 110.8(3) . . ? N2 C1 N1 108.3(3) . . ? C3 C2 N2 107.1(3) . . ? C3 C2 C6 130.5(4) . . ? N2 C2 C6 122.3(4) . . ? C2 C3 N1 106.7(3) . . ? C2 C3 C5 131.5(3) . . ? N1 C3 C5 121.8(4) . . ? C16 C8 C9 110.9(3) . . ? C8 C9 C10 106.5(3) . . ? C9 C10 C11 132.7(4) . . ? C9 C10 C15 108.2(3) . . ? C11 C10 C15 119.1(3) . . ? C12 C11 C10 119.4(4) . . ? C11 C12 C13 121.9(4) . . ? C14 C13 C12 119.4(4) . . ? C15 C14 C13 121.0(4) . . ? C14 C15 C16 133.2(4) . . ? C14 C15 C10 119.3(3) . . ? C16 C15 C10 107.6(3) . . ? C8 C16 C15 106.8(3) . . ? C8 C16 C17 127.9(3) . . ? C15 C16 C17 124.9(3) . . ? C19 C18 N4 109.8(3) . . ? C19 C18 C22 129.5(4) . . ? N4 C18 C22 119.2(3) . . ? C18 C19 N3 109.6(3) . . ? C18 C19 C21 130.3(4) . . ? N3 C19 C21 119.5(3) . . ? C1 N1 C3 108.9(3) . . ? C1 N1 C4 124.6(3) . . ? C3 N1 C4 126.1(3) . . ? C1 N2 C2 109.1(3) . . ? C1 N2 C7 125.0(3) . . ? C2 N2 C7 125.9(3) . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.201 _refine_diff_density_min -0.182 _refine_diff_density_rms 0.047 data_p21overn _database_code_CSD 220955 _audit_creation_method SHELXL-97 _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C50 H54 N2 O2' _chemical_formula_weight 714.95 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 13.812(5) _cell_length_b 14.539(5) _cell_length_c 20.663(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 104.162(5) _cell_angle_gamma 90.000(5) _cell_volume 4023(2) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used all _cell_measurement_theta_min 2.98 _cell_measurement_theta_max 27.52 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.180 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1536 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9860 _exptl_absorpt_correction_T_max 0.9860 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17054 _diffrn_reflns_av_R_equivalents 0.1418 _diffrn_reflns_av_sigmaI/netI 0.2070 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 27.52 _reflns_number_total 9201 _reflns_number_gt 3632 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement DENZO _computing_data_reduction Scalepack _computing_structure_solution 'WinGX (Farrugia, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _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. ; _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^)+(0.0107P)^2^+5.0539P] 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 SHELXL _refine_ls_extinction_coef 0.0022(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 9201 _refine_ls_number_parameters 704 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2469 _refine_ls_R_factor_gt 0.0887 _refine_ls_wR_factor_ref 0.1615 _refine_ls_wR_factor_gt 0.1174 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _refine_ls_shift/su_max 0.037 _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 C1 C 0.7049(2) 0.0288(2) 0.71400(16) 0.0242(8) Uani 1 1 d . . . C2 C 0.7667(3) 0.0042(2) 0.77707(16) 0.0250(8) Uani 1 1 d . . . C3 C 0.8656(2) -0.0064(2) 0.77016(16) 0.0252(8) Uani 1 1 d . . . C4 C 0.8655(2) 0.0122(2) 0.70246(16) 0.0253(8) Uani 1 1 d . . . C5 C 0.7667(2) 0.0335(2) 0.66795(16) 0.0245(8) Uani 1 1 d . . . C6 C 0.7329(2) -0.0120(2) 0.83896(16) 0.0256(8) Uani 1 1 d . . . C7 C 0.7614(3) -0.0920(3) 0.87712(18) 0.0313(9) Uani 1 1 d . . . C8 C 0.7297(3) -0.1074(3) 0.93540(19) 0.0360(10) Uani 1 1 d . . . C9 C 0.6686(3) -0.0443(3) 0.9560(2) 0.0380(10) Uani 1 1 d . . . C10 C 0.6389(3) 0.0347(3) 0.91886(19) 0.0373(10) Uani 1 1 d . . . C11 C 0.6707(3) 0.0499(3) 0.86053(18) 0.0308(9) Uani 1 1 d . . . C12 C 0.9543(3) -0.0293(2) 0.82387(16) 0.0241(8) Uani 1 1 d . . . C13 C 0.9742(3) 0.0144(3) 0.88613(17) 0.0279(9) Uani 1 1 d . . . C14 C 1.0626(3) -0.0016(3) 0.93460(19) 0.0331(9) Uani 1 1 d . . . C15 C 1.1323(3) -0.0634(3) 0.92206(19) 0.0350(10) Uani 1 1 d . . . C16 C 1.1133(3) -0.1090(3) 0.8617(2) 0.0347(10) Uani 1 1 d . . . C17 C 1.0253(3) -0.0935(3) 0.81372(19) 0.0305(9) Uani 1 1 d . . . C18 C 0.9531(3) 0.0082(2) 0.67357(16) 0.0281(9) Uani 1 1 d . . . C19 C 1.0441(3) 0.0489(3) 0.70577(19) 0.0335(9) Uani 1 1 d . . . C20 C 1.1264(3) 0.0449(3) 0.6786(2) 0.0395(10) Uani 1 1 d . . . C21 C 1.1214(3) 0.0008(3) 0.6185(2) 0.0417(11) Uani 1 1 d . . . C22 C 1.0324(3) -0.0389(3) 0.5855(2) 0.0403(11) Uani 1 1 d . . . C23 C 0.9499(3) -0.0363(3) 0.61243(18) 0.0340(10) Uani 1 1 d . . . C24 C 0.7330(3) 0.0565(2) 0.59622(16) 0.0255(8) Uani 1 1 d . . . C25 C 0.7837(3) 0.1215(3) 0.56714(18) 0.0315(9) Uani 1 1 d . . . C26 C 0.7559(3) 0.1391(3) 0.49859(18) 0.0345(10) Uani 1 1 d . . . C27 C 0.6760(3) 0.0928(3) 0.45784(18) 0.0354(10) Uani 1 1 d . . . C28 C 0.6237(3) 0.0289(3) 0.48627(18) 0.0332(9) Uani 1 1 d . . . C29 C 0.6517(3) 0.0112(3) 0.55486(17) 0.0301(9) Uani 1 1 d . . . C30 C 0.5977(3) 0.0507(2) 0.69830(16) 0.0268(8) Uani 1 1 d . . . C31 C 0.5616(3) 0.1315(3) 0.66359(17) 0.0292(9) Uani 1 1 d . . . C32 C 0.4607(3) 0.1543(3) 0.64926(19) 0.0363(10) Uani 1 1 d . . . C33 C 0.3935(3) 0.0975(3) 0.66935(19) 0.0403(11) Uani 1 1 d . . . C34 C 0.4273(3) 0.0177(3) 0.7039(2) 0.0403(11) Uani 1 1 d . . . C35 C 0.5277(3) -0.0051(3) 0.71813(18) 0.0328(9) Uani 1 1 d . . . C36 C 0.9786(3) 0.2435(3) 0.8721(2) 0.0377(10) Uani 1 1 d . . . C37 C 0.8148(3) 0.2654(2) 0.84714(18) 0.0313(9) Uani 1 1 d . . . C38 C 0.8479(3) 0.2638(2) 0.91495(18) 0.0300(9) Uani 1 1 d . . . C39 C 0.8971(5) 0.2424(4) 0.7509(2) 0.0548(14) Uani 1 1 d . . . C40 C 0.7142(4) 0.2808(4) 0.8031(2) 0.0478(12) Uani 1 1 d . . . C41 C 0.7918(4) 0.2742(3) 0.9672(2) 0.0435(11) Uani 1 1 d . . . C42 C 1.0168(4) 0.2425(4) 0.9964(2) 0.0460(11) Uani 1 1 d . . . C43 C 0.2600(5) 0.2759(5) 0.8020(4) 0.087(2) Uani 1 1 d . . . C44 C 0.3621(5) 0.2391(4) 0.8241(4) 0.0818(19) Uani 1 1 d . . . C45 C 0.3530(5) 0.1549(6) 0.8616(4) 0.101(3) Uani 1 1 d . . . C46 C 0.2473(4) 0.1427(4) 0.8604(3) 0.0640(14) Uani 1 1 d . . . C47 C 0.0957(5) 0.2435(4) 0.5469(4) 0.096(2) Uani 1 1 d . . . C48 C 0.0155(5) 0.2508(5) 0.5829(5) 0.099(2) Uani 1 1 d . . . C49 C 0.0483(5) 0.3276(7) 0.6346(3) 0.105(3) Uani 1 1 d . . . C50 C 0.1054(5) 0.3889(5) 0.5976(4) 0.087(2) Uani 1 1 d . . . N1 N 0.9501(2) 0.2509(2) 0.92916(14) 0.0342(8) Uani 1 1 d . . . N3 N 0.8980(2) 0.2524(2) 0.82190(14) 0.0345(8) Uani 1 1 d . . . O1 O 0.1951(2) 0.2226(2) 0.83093(18) 0.0745(10) Uani 1 1 d . . . O2 O 0.1496(3) 0.3264(3) 0.5597(2) 0.0985(13) Uani 1 1 d . . . H7 H 0.813(3) -0.141(3) 0.8616(17) 0.053(12) Uiso 1 1 d . . . H8 H 0.751(2) -0.165(2) 0.9609(17) 0.041(11) Uiso 1 1 d . . . H9 H 0.648(3) -0.055(3) 0.997(2) 0.077(15) Uiso 1 1 d . . . H10 H 0.595(3) 0.081(3) 0.9332(19) 0.061(13) Uiso 1 1 d . . . H11 H 0.646(3) 0.109(3) 0.8351(18) 0.059(13) Uiso 1 1 d . . . H13 H 0.925(2) 0.062(2) 0.8968(16) 0.036(10) Uiso 1 1 d . . . H14 H 1.077(3) 0.033(3) 0.980(2) 0.075(14) Uiso 1 1 d . . . H15 H 1.196(3) -0.072(3) 0.9596(18) 0.054(12) Uiso 1 1 d . . . H16 H 1.164(3) -0.153(3) 0.8511(18) 0.053(12) Uiso 1 1 d . . . H19 H 1.047(3) 0.084(3) 0.7493(19) 0.057(12) Uiso 1 1 d . . . H20 H 1.194(3) 0.074(3) 0.7022(18) 0.056(12) Uiso 1 1 d . . . H21 H 1.182(3) 0.004(2) 0.6009(17) 0.047(11) Uiso 1 1 d . . . H22 H 1.026(2) -0.074(2) 0.5442(17) 0.038(10) Uiso 1 1 d . . . H23 H 0.886(3) -0.067(2) 0.5914(17) 0.041(11) Uiso 1 1 d . . . H24 H 1.014(3) -0.128(2) 0.7691(18) 0.048(11) Uiso 1 1 d . . . H25 H 0.848(3) 0.153(2) 0.5971(18) 0.050(11) Uiso 1 1 d . . . H26 H 0.792(3) 0.183(3) 0.4794(18) 0.051(12) Uiso 1 1 d . . . H27 H 0.655(3) 0.104(2) 0.4056(19) 0.054(11) Uiso 1 1 d . . . H28 H 0.561(3) -0.009(3) 0.4549(19) 0.068(13) Uiso 1 1 d . . . H29 H 0.614(3) -0.038(2) 0.5736(16) 0.040(11) Uiso 1 1 d . . . H31 H 0.608(2) 0.173(2) 0.6477(15) 0.025(9) Uiso 1 1 d . . . H32 H 0.439(3) 0.216(3) 0.6245(17) 0.049(12) Uiso 1 1 d . . . H33 H 0.320(3) 0.112(3) 0.6564(18) 0.052(12) Uiso 1 1 d . . . H34 H 0.380(3) -0.020(3) 0.7170(19) 0.060(14) Uiso 1 1 d . . . H35 H 0.554(3) -0.062(3) 0.7428(18) 0.058(13) Uiso 1 1 d . . . H36 H 1.046(3) 0.233(3) 0.8667(18) 0.052(12) Uiso 1 1 d . . . H39A H 0.857(3) 0.188(3) 0.732(2) 0.076(16) Uiso 1 1 d . . . H39B H 0.856(3) 0.294(3) 0.7288(19) 0.057(14) Uiso 1 1 d . . . H39C H 0.971(4) 0.242(4) 0.747(3) 0.13(2) Uiso 1 1 d . . . H40A H 0.700(3) 0.235(3) 0.773(2) 0.083(18) Uiso 1 1 d . . . H40B H 0.656(3) 0.285(3) 0.833(2) 0.074(14) Uiso 1 1 d . . . H40C H 0.710(3) 0.341(3) 0.775(2) 0.074(14) Uiso 1 1 d . . . H41A H 0.813(3) 0.325(3) 0.995(2) 0.082(17) Uiso 1 1 d . . . H41B H 0.806(3) 0.214(4) 1.005(2) 0.105(17) Uiso 1 1 d . . . H41C H 0.721(4) 0.275(3) 0.947(2) 0.10(2) Uiso 1 1 d . . . H42A H 0.991(3) 0.190(3) 1.0228(19) 0.062(13) Uiso 1 1 d . . . H42B H 1.011(3) 0.303(3) 1.018(2) 0.080(16) Uiso 1 1 d . . . H42C H 1.087(3) 0.232(3) 0.9894(19) 0.069(14) Uiso 1 1 d . . . H43A H 0.232(6) 0.330(6) 0.802(4) 0.17(4) Uiso 1 1 d . . . H43B H 0.232(9) 0.266(8) 0.749(7) 0.34(7) Uiso 1 1 d . . . H44A H 0.408(6) 0.291(6) 0.852(4) 0.21(4) Uiso 1 1 d . . . H44B H 0.399(7) 0.232(6) 0.790(5) 0.25(5) Uiso 1 1 d . . . H45A H 0.382(9) 0.188(9) 0.908(6) 0.31(7) Uiso 1 1 d . . . H45B H 0.404(5) 0.112(4) 0.879(3) 0.13(2) Uiso 1 1 d . . . H46A H 0.210(8) 0.075(8) 0.837(5) 0.34(6) Uiso 1 1 d . . . H46B H 0.239(4) 0.137(4) 0.911(3) 0.15(2) Uiso 1 1 d . . . H47A H 0.148(5) 0.189(5) 0.565(3) 0.16(3) Uiso 1 1 d . . . H47B H 0.042(4) 0.313(4) 0.524(2) 0.104(18) Uiso 1 1 d . . . H48A H -0.052(4) 0.268(4) 0.545(3) 0.12(2) Uiso 1 1 d . . . H48B H 0.016(6) 0.188(7) 0.618(5) 0.26(4) Uiso 1 1 d . . . H49A H -0.010(5) 0.357(4) 0.645(3) 0.14(2) Uiso 1 1 d . . . H49B H 0.092(4) 0.287(4) 0.668(3) 0.095(18) Uiso 1 1 d . . . H50A H 0.058(4) 0.433(4) 0.561(3) 0.12(2) Uiso 1 1 d . . . H50B H 0.159(4) 0.420(4) 0.634(3) 0.13(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 C1 0.022(2) 0.024(2) 0.0241(18) -0.0005(16) 0.0009(15) 0.0003(16) C2 0.026(2) 0.025(2) 0.0242(19) -0.0009(16) 0.0071(16) 0.0011(17) C3 0.024(2) 0.025(2) 0.0243(19) -0.0021(16) 0.0014(16) -0.0007(17) C4 0.023(2) 0.029(2) 0.0243(19) 0.0009(16) 0.0059(16) 0.0008(17) C5 0.024(2) 0.027(2) 0.0218(18) 0.0024(16) 0.0028(15) -0.0003(16) C6 0.022(2) 0.025(2) 0.0280(19) -0.0012(17) 0.0032(15) -0.0019(16) C7 0.029(2) 0.029(2) 0.034(2) 0.0045(18) 0.0045(18) -0.0036(19) C8 0.031(2) 0.041(3) 0.033(2) 0.013(2) 0.0025(19) -0.003(2) C9 0.031(2) 0.050(3) 0.030(2) 0.009(2) 0.0033(18) -0.008(2) C10 0.038(3) 0.043(3) 0.033(2) -0.005(2) 0.0131(19) -0.002(2) C11 0.033(2) 0.030(2) 0.030(2) -0.0041(19) 0.0099(17) -0.0018(19) C12 0.024(2) 0.022(2) 0.0270(19) -0.0020(16) 0.0075(15) -0.0011(16) C13 0.025(2) 0.031(2) 0.028(2) -0.0018(17) 0.0079(17) -0.0033(18) C14 0.030(2) 0.036(2) 0.031(2) 0.004(2) 0.0034(18) -0.009(2) C15 0.031(2) 0.034(2) 0.035(2) 0.007(2) -0.0020(19) -0.008(2) C16 0.025(2) 0.033(2) 0.044(3) 0.006(2) 0.0043(19) 0.0029(19) C17 0.029(2) 0.029(2) 0.033(2) 0.0007(18) 0.0048(18) -0.0009(19) C18 0.024(2) 0.033(2) 0.0257(19) 0.0015(17) 0.0020(16) 0.0022(17) C19 0.029(2) 0.039(2) 0.034(2) -0.001(2) 0.0107(18) -0.0013(19) C20 0.027(2) 0.047(3) 0.046(3) -0.001(2) 0.011(2) -0.004(2) C21 0.035(3) 0.046(3) 0.048(3) 0.005(2) 0.019(2) 0.006(2) C22 0.048(3) 0.043(3) 0.033(2) 0.000(2) 0.017(2) 0.008(2) C23 0.038(3) 0.033(2) 0.030(2) -0.0021(18) 0.0067(19) 0.000(2) C24 0.026(2) 0.026(2) 0.0243(19) -0.0008(17) 0.0050(16) 0.0023(17) C25 0.033(2) 0.033(2) 0.028(2) -0.0031(18) 0.0075(18) -0.0034(19) C26 0.045(3) 0.034(2) 0.027(2) 0.0044(19) 0.0143(19) 0.004(2) C27 0.041(3) 0.043(2) 0.021(2) 0.0004(19) 0.0053(18) 0.010(2) C28 0.035(2) 0.034(2) 0.028(2) -0.0054(18) 0.0019(18) 0.0112(19) C29 0.033(2) 0.031(2) 0.026(2) -0.0026(18) 0.0051(17) 0.0013(19) C30 0.027(2) 0.029(2) 0.0240(19) -0.0030(17) 0.0063(16) 0.0001(18) C31 0.029(2) 0.029(2) 0.029(2) -0.0028(18) 0.0046(17) 0.0014(19) C32 0.039(3) 0.036(2) 0.033(2) 0.000(2) 0.0061(19) 0.009(2) C33 0.030(3) 0.053(3) 0.036(2) -0.010(2) 0.005(2) 0.004(2) C34 0.032(3) 0.049(3) 0.041(2) -0.003(2) 0.010(2) -0.006(2) C35 0.032(2) 0.033(2) 0.033(2) -0.002(2) 0.0095(18) -0.002(2) C36 0.039(3) 0.030(2) 0.047(3) 0.000(2) 0.017(2) -0.001(2) C37 0.037(2) 0.020(2) 0.035(2) 0.0023(17) 0.0055(19) 0.0005(17) C38 0.031(2) 0.023(2) 0.036(2) 0.0042(17) 0.0069(17) -0.0001(18) C39 0.096(5) 0.038(3) 0.035(3) -0.004(2) 0.024(3) 0.000(3) C40 0.048(3) 0.040(3) 0.045(3) 0.007(3) -0.007(2) -0.002(2) C41 0.050(3) 0.042(3) 0.041(3) 0.003(2) 0.017(2) 0.001(2) C42 0.043(3) 0.050(3) 0.040(3) 0.008(2) 0.001(2) -0.002(3) C43 0.070(5) 0.071(5) 0.113(6) 0.038(4) 0.010(4) -0.008(4) C44 0.082(5) 0.060(4) 0.116(5) -0.017(4) 0.050(4) -0.016(4) C45 0.061(5) 0.110(6) 0.139(7) 0.061(6) 0.040(4) 0.028(4) C46 0.058(4) 0.070(4) 0.061(3) 0.025(3) 0.008(3) 0.001(3) C47 0.065(4) 0.055(4) 0.176(7) 0.008(4) 0.045(4) -0.021(4) C48 0.060(4) 0.091(5) 0.155(7) 0.057(5) 0.046(5) 0.011(4) C49 0.060(4) 0.211(9) 0.052(4) 0.042(5) 0.029(3) 0.050(6) C50 0.045(4) 0.085(5) 0.140(6) -0.048(5) 0.039(4) -0.009(4) N1 0.036(2) 0.0309(18) 0.0353(19) 0.0027(15) 0.0073(15) -0.0037(16) N3 0.049(2) 0.0239(18) 0.0317(18) -0.0026(15) 0.0118(16) -0.0013(16) O1 0.059(2) 0.064(2) 0.104(3) 0.006(2) 0.024(2) 0.0076(19) O2 0.102(3) 0.093(3) 0.122(3) -0.030(3) 0.070(3) -0.039(3) _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 C1 C2 1.418(4) . ? C1 C5 1.427(4) . ? C1 C30 1.471(5) . ? C2 C3 1.415(4) . ? C2 C6 1.484(4) . ? C3 C4 1.425(4) . ? C3 C12 1.476(4) . ? C4 C5 1.411(4) . ? C4 C18 1.476(4) . ? C5 C24 1.479(4) . ? C6 C11 1.391(5) . ? C6 C7 1.406(5) . ? C7 C8 1.397(5) . ? C8 C9 1.383(5) . ? C9 C10 1.387(5) . ? C10 C11 1.398(5) . ? C12 C13 1.400(5) . ? C12 C17 1.406(5) . ? C13 C14 1.396(5) . ? C14 C15 1.388(5) . ? C15 C16 1.380(5) . ? C16 C17 1.386(5) . ? C18 C19 1.400(5) . ? C18 C23 1.410(5) . ? C19 C20 1.387(5) . ? C20 C21 1.384(5) . ? C21 C22 1.378(6) . ? C22 C23 1.386(5) . ? C24 C25 1.396(5) . ? C24 C29 1.398(5) . ? C25 C26 1.398(5) . ? C26 C27 1.388(5) . ? C27 C28 1.391(5) . ? C28 C29 1.399(5) . ? C30 C35 1.399(5) . ? C30 C31 1.403(5) . ? C31 C32 1.392(5) . ? C32 C33 1.381(5) . ? C33 C34 1.383(6) . ? C34 C35 1.385(5) . ? C36 N3 1.328(5) . ? C36 N1 1.336(5) . ? C37 C38 1.364(5) . ? C37 N3 1.386(4) . ? C37 C40 1.481(5) . ? C38 N1 1.382(4) . ? C38 C41 1.483(5) . ? C39 N3 1.472(5) . ? C42 N1 1.472(5) . ? C43 O1 1.424(7) . ? C43 C44 1.473(9) . ? C44 C45 1.471(9) . ? C45 C46 1.464(8) . ? C46 O1 1.423(5) . ? C47 O2 1.407(6) . ? C47 C48 1.481(8) . ? C48 C49 1.535(10) . ? C49 C50 1.515(9) . ? C50 O2 1.430(6) . ? 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 C2 C1 C5 107.5(3) . . ? C2 C1 C30 127.2(3) . . ? C5 C1 C30 125.2(3) . . ? C3 C2 C1 108.3(3) . . ? C3 C2 C6 125.8(3) . . ? C1 C2 C6 125.9(3) . . ? C2 C3 C4 108.0(3) . . ? C2 C3 C12 126.4(3) . . ? C4 C3 C12 125.6(3) . . ? C5 C4 C3 107.8(3) . . ? C5 C4 C18 126.3(3) . . ? C3 C4 C18 125.9(3) . . ? C4 C5 C1 108.4(3) . . ? C4 C5 C24 125.8(3) . . ? C1 C5 C24 125.9(3) . . ? C11 C6 C7 117.8(3) . . ? C11 C6 C2 121.5(3) . . ? C7 C6 C2 120.7(3) . . ? C8 C7 C6 120.8(4) . . ? C9 C8 C7 120.2(4) . . ? C8 C9 C10 120.0(4) . . ? C9 C10 C11 119.7(4) . . ? C6 C11 C10 121.5(4) . . ? C13 C12 C17 116.8(3) . . ? C13 C12 C3 121.9(3) . . ? C17 C12 C3 121.2(3) . . ? C14 C13 C12 121.6(4) . . ? C15 C14 C13 119.9(4) . . ? C16 C15 C14 119.5(4) . . ? C15 C16 C17 120.6(4) . . ? C16 C17 C12 121.5(4) . . ? C19 C18 C23 116.6(3) . . ? C19 C18 C4 121.4(3) . . ? C23 C18 C4 122.1(3) . . ? C20 C19 C18 121.3(4) . . ? C21 C20 C19 121.0(4) . . ? C22 C21 C20 118.8(4) . . ? C21 C22 C23 120.7(4) . . ? C22 C23 C18 121.5(4) . . ? C25 C24 C29 117.9(3) . . ? C25 C24 C5 121.1(3) . . ? C29 C24 C5 121.0(3) . . ? C24 C25 C26 121.2(4) . . ? C27 C26 C25 120.4(4) . . ? C26 C27 C28 119.0(4) . . ? C27 C28 C29 120.5(4) . . ? C24 C29 C28 121.0(4) . . ? C35 C30 C31 116.8(3) . . ? C35 C30 C1 122.7(3) . . ? C31 C30 C1 120.5(3) . . ? C32 C31 C30 121.4(4) . . ? C33 C32 C31 120.3(4) . . ? C32 C33 C34 119.4(4) . . ? C33 C34 C35 120.3(4) . . ? C34 C35 C30 121.8(4) . . ? N3 C36 N1 108.0(4) . . ? C38 C37 N3 106.5(3) . . ? C38 C37 C40 131.5(4) . . ? N3 C37 C40 122.0(4) . . ? C37 C38 N1 106.8(3) . . ? C37 C38 C41 130.0(4) . . ? N1 C38 C41 123.2(4) . . ? O1 C43 C44 108.9(5) . . ? C45 C44 C43 105.5(5) . . ? C46 C45 C44 107.8(6) . . ? O1 C46 C45 107.9(5) . . ? O2 C47 C48 105.7(6) . . ? C47 C48 C49 105.8(5) . . ? C50 C49 C48 100.3(5) . . ? O2 C50 C49 104.3(6) . . ? C36 N1 C38 109.2(3) . . ? C36 N1 C42 125.1(4) . . ? C38 N1 C42 125.6(3) . . ? C36 N3 C37 109.4(3) . . ? C36 N3 C39 124.7(4) . . ? C37 N3 C39 125.7(4) . . ? C46 O1 C43 108.6(4) . . ? C47 O2 C50 111.8(4) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.261 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.061 data_p1bar _database_code_CSD 220956 _audit_creation_method SHELXL-97 _chemical_name_common ? _chemical_melting_point '[C21 H25 N2][C5 H5]' _chemical_formula_moiety ? _chemical_formula_sum 'C26 H31 N2' _chemical_formula_weight 371.53 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 8.3933(17) _cell_length_b 8.9198(18) _cell_length_c 16.085(3) _cell_angle_alpha 79.99(3) _cell_angle_beta 82.41(3) _cell_angle_gamma 65.62(3) _cell_volume 1077.7(4) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used all _cell_measurement_theta_min 2.99 _cell_measurement_theta_max 27.58 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.145 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 402 _exptl_absorpt_coefficient_mu 0.066 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9869 _exptl_absorpt_correction_T_max 0.9869 _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 'Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7217 _diffrn_reflns_av_R_equivalents 0.0694 _diffrn_reflns_av_sigmaI/netI 0.1881 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 27.58 _reflns_number_total 4861 _reflns_number_gt 2287 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement DENZO _computing_data_reduction Scalepack _computing_structure_solution 'WinGX (Farrugia, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _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. ; _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^)+(0.2000P)^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 SHELXL _refine_ls_extinction_coef 0.38(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4861 _refine_ls_number_parameters 269 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.3367 _refine_ls_R_factor_gt 0.2405 _refine_ls_wR_factor_ref 0.5904 _refine_ls_wR_factor_gt 0.5673 _refine_ls_goodness_of_fit_ref 1.862 _refine_ls_restrained_S_all 1.862 _refine_ls_shift/su_max 0.027 _refine_ls_shift/su_mean 0.003 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 H14 H 0.679(11) 0.862(10) -0.050(5) 0.05(2) Uiso 1 1 d . . . H22 H 1.691(11) -0.214(9) 0.311(5) 0.03(2) Uiso 1 1 d . . . C1 C 1.3148(14) 0.4784(15) 0.3142(6) 0.055(3) Uani 1 1 d . . . H1 H 1.2913 0.5004 0.3712 0.066 Uiso 1 1 calc R . . C2 C 1.2711(11) 0.5987(12) 0.2420(7) 0.049(3) Uani 1 1 d . . . H2 H 1.2136 0.7156 0.2413 0.059 Uiso 1 1 calc R . . C3 C 1.3275(12) 0.5145(13) 0.1730(6) 0.048(3) Uani 1 1 d . . . H3 H 1.3152 0.5637 0.1156 0.057 Uiso 1 1 calc R . . C4 C 1.4054(13) 0.3458(14) 0.2005(8) 0.059(3) Uani 1 1 d . . . H4 H 1.4557 0.2600 0.1655 0.071 Uiso 1 1 calc R . . C5 C 1.3972(13) 0.3241(12) 0.2883(6) 0.046(2) Uani 1 1 d . . . H5 H 1.4406 0.2211 0.3240 0.055 Uiso 1 1 calc R . . C6 C 0.9877(11) 0.4240(11) 0.2562(5) 0.038(2) Uani 1 1 d . . . H6 H 1.0934 0.4410 0.2440 0.046 Uiso 1 1 calc R . . C8 C 0.7164(13) 0.4560(12) 0.2532(6) 0.049(3) Uani 1 1 d . . . H8 H 0.5971 0.5013 0.2402 0.059 Uiso 1 1 calc R . . C9 C 0.7987(13) 0.3120(12) 0.3004(6) 0.047(3) Uani 1 1 d . . . H9 H 0.7494 0.2353 0.3264 0.056 Uiso 1 1 calc R . . C10 C 0.8023(11) 0.6784(11) 0.1710(6) 0.041(2) Uani 1 1 d . . . C11 C 0.7984(11) 0.8166(11) 0.2047(6) 0.041(2) Uani 1 1 d . . . C12 C 0.7720(13) 0.9630(13) 0.1487(7) 0.053(3) Uani 1 1 d . . . H12 H 0.7708 1.0569 0.1696 0.063 Uiso 1 1 calc R . . C13 C 0.7477(13) 0.9744(13) 0.0646(6) 0.051(3) Uani 1 1 d . . . C14 C 0.7540(14) 0.8341(14) 0.0347(6) 0.057(3) Uani 1 1 d . . . C15 C 0.7798(11) 0.6830(11) 0.0861(6) 0.041(2) Uani 1 1 d . . . C16 C 0.8091(14) 0.8127(11) 0.2969(6) 0.047(3) Uani 1 1 d . . . H16A H 0.7655 0.7319 0.3293 0.071 Uiso 1 1 calc R . . H16B H 0.7375 0.9230 0.3134 0.071 Uiso 1 1 calc R . . H16C H 0.9313 0.7806 0.3088 0.071 Uiso 1 1 calc R . . C17 C 0.7273(16) 1.1261(13) 0.0057(7) 0.065(3) Uani 1 1 d . . . H17A H 0.6695 1.2231 0.0360 0.098 Uiso 1 1 calc R . . H17B H 0.6558 1.1358 -0.0401 0.098 Uiso 1 1 calc R . . H17C H 0.8429 1.1205 -0.0182 0.098 Uiso 1 1 calc R . . C18 C 0.7838(15) 0.5365(13) 0.0541(7) 0.061(3) Uani 1 1 d . . . H18A H 0.6656 0.5376 0.0604 0.092 Uiso 1 1 calc R . . H18B H 0.8633 0.4354 0.0864 0.092 Uiso 1 1 calc R . . H18C H 0.8252 0.5390 -0.0058 0.092 Uiso 1 1 calc R . . C20 C 1.1053(12) 0.1548(11) 0.3465(6) 0.039(2) Uani 1 1 d . . . C21 C 1.2181(12) 0.0283(12) 0.3014(6) 0.042(2) Uani 1 1 d . . . C22 C 1.3439(12) -0.1060(12) 0.3451(6) 0.047(3) Uani 1 1 d . . . H22A H 1.4237 -0.1924 0.3145 0.057 Uiso 1 1 calc R . . C23 C 1.3597(12) -0.1215(11) 0.4302(6) 0.040(2) Uani 1 1 d . . . C24 C 1.2423(14) 0.0089(12) 0.4738(6) 0.048(3) Uani 1 1 d . . . H24 H 1.2521 0.0019 0.5327 0.058 Uiso 1 1 calc R . . C25 C 1.1120(13) 0.1483(11) 0.4339(6) 0.042(2) Uani 1 1 d . . . C26 C 1.2114(14) 0.0414(13) 0.2085(6) 0.056(3) Uani 1 1 d . . . H26A H 1.1012 0.0392 0.1962 0.084 Uiso 1 1 calc R . . H26B H 1.3103 -0.0522 0.1868 0.084 Uiso 1 1 calc R . . H26C H 1.2184 0.1458 0.1811 0.084 Uiso 1 1 calc R . . C27 C 1.4974(13) -0.2712(12) 0.4787(7) 0.055(3) Uani 1 1 d . . . H27A H 1.5151 -0.3722 0.4557 0.082 Uiso 1 1 calc R . . H27B H 1.4573 -0.2807 0.5386 0.082 Uiso 1 1 calc R . . H27C H 1.6082 -0.2569 0.4727 0.082 Uiso 1 1 calc R . . C28 C 0.9911(14) 0.2865(12) 0.4805(6) 0.056(3) Uani 1 1 d . . . H28A H 1.0328 0.2719 0.5367 0.084 Uiso 1 1 calc R . . H28B H 0.8733 0.2867 0.4865 0.084 Uiso 1 1 calc R . . H28C H 0.9874 0.3923 0.4491 0.084 Uiso 1 1 calc R . . N1 N 0.9700(9) 0.2944(9) 0.3046(4) 0.0382(19) Uani 1 1 d . . . N2 N 0.8321(9) 0.5265(9) 0.2273(5) 0.0387(19) 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 C1 0.055(7) 0.087(9) 0.044(6) -0.009(6) -0.010(5) -0.048(6) C2 0.025(5) 0.039(6) 0.089(8) -0.011(5) -0.011(5) -0.016(4) C3 0.037(6) 0.061(7) 0.053(6) -0.005(5) -0.007(4) -0.028(5) C4 0.042(6) 0.057(7) 0.090(9) -0.031(6) 0.005(5) -0.024(5) C5 0.046(6) 0.045(6) 0.047(6) 0.007(5) -0.003(4) -0.024(5) C6 0.017(5) 0.051(6) 0.053(6) -0.010(5) -0.005(4) -0.017(4) C8 0.040(6) 0.045(6) 0.065(7) -0.002(5) -0.009(5) -0.021(5) C9 0.050(6) 0.041(6) 0.061(6) -0.006(5) 0.001(5) -0.031(5) C10 0.027(5) 0.039(5) 0.050(6) -0.005(4) -0.006(4) -0.004(4) C11 0.027(5) 0.040(5) 0.055(6) -0.008(5) -0.004(4) -0.013(4) C12 0.036(6) 0.056(7) 0.074(7) -0.021(6) 0.003(5) -0.024(5) C13 0.048(6) 0.050(6) 0.051(6) -0.006(5) -0.014(5) -0.012(5) C14 0.056(7) 0.064(7) 0.053(6) -0.012(5) -0.004(5) -0.024(6) C15 0.030(5) 0.041(6) 0.054(6) 0.000(4) -0.009(4) -0.017(4) C16 0.048(6) 0.033(5) 0.053(6) -0.007(4) -0.004(4) -0.007(5) C17 0.082(9) 0.048(7) 0.071(8) 0.003(5) -0.009(6) -0.034(6) C18 0.068(8) 0.052(7) 0.077(8) -0.019(6) -0.008(6) -0.032(6) C20 0.035(5) 0.046(6) 0.045(5) -0.009(4) -0.001(4) -0.024(4) C21 0.042(6) 0.044(6) 0.049(6) -0.001(4) -0.010(4) -0.026(5) C22 0.032(5) 0.044(6) 0.059(7) -0.014(5) -0.003(4) -0.006(4) C23 0.035(5) 0.042(5) 0.050(6) -0.005(4) -0.008(4) -0.021(4) C24 0.073(7) 0.042(6) 0.040(5) 0.006(4) -0.017(5) -0.033(5) C25 0.049(6) 0.034(5) 0.051(6) -0.004(4) -0.007(4) -0.025(5) C26 0.059(7) 0.047(6) 0.059(7) -0.014(5) -0.011(5) -0.014(5) C27 0.049(6) 0.040(6) 0.068(7) 0.003(5) -0.016(5) -0.011(5) C28 0.059(7) 0.045(6) 0.059(7) -0.010(5) -0.013(5) -0.013(5) N1 0.032(4) 0.045(5) 0.042(4) 0.000(3) -0.007(3) -0.021(4) N2 0.032(4) 0.040(4) 0.052(5) -0.005(3) -0.002(3) -0.023(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 C1 C5 1.372(14) . ? C1 C2 1.411(14) . ? C2 C3 1.370(13) . ? C3 C4 1.386(15) . ? C4 C5 1.387(14) . ? C6 N1 1.328(11) . ? C6 N2 1.336(11) . ? C8 C9 1.331(13) . ? C8 N2 1.348(11) . ? C9 N1 1.390(11) . ? C10 C15 1.393(13) . ? C10 C11 1.417(13) . ? C10 N2 1.440(11) . ? C11 C12 1.404(14) . ? C11 C16 1.492(13) . ? C12 C13 1.375(14) . ? C13 C14 1.396(14) . ? C13 C17 1.471(14) . ? C14 C15 1.402(14) . ? C15 C18 1.473(13) . ? C20 C21 1.384(13) . ? C20 C25 1.403(12) . ? C20 N1 1.428(11) . ? C21 C22 1.379(12) . ? C21 C26 1.486(13) . ? C22 C23 1.371(12) . ? C23 C24 1.404(13) . ? C23 C27 1.526(12) . ? C24 C25 1.393(13) . ? C25 C28 1.483(13) . ? 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 C1 C2 108.6(9) . . ? C3 C2 C1 106.8(9) . . ? C2 C3 C4 108.9(9) . . ? C3 C4 C5 108.0(9) . . ? C1 C5 C4 107.7(9) . . ? N1 C6 N2 108.6(7) . . ? C9 C8 N2 108.0(8) . . ? C8 C9 N1 107.4(8) . . ? C15 C10 C11 123.0(8) . . ? C15 C10 N2 118.9(8) . . ? C11 C10 N2 118.1(8) . . ? C12 C11 C10 117.4(8) . . ? C12 C11 C16 120.4(8) . . ? C10 C11 C16 122.0(8) . . ? C13 C12 C11 121.8(9) . . ? C12 C13 C14 118.3(9) . . ? C12 C13 C17 121.4(10) . . ? C14 C13 C17 120.2(9) . . ? C13 C14 C15 123.7(9) . . ? C10 C15 C14 115.8(9) . . ? C10 C15 C18 121.1(8) . . ? C14 C15 C18 123.1(9) . . ? C21 C20 C25 122.6(8) . . ? C21 C20 N1 119.6(7) . . ? C25 C20 N1 117.7(8) . . ? C22 C21 C20 117.5(8) . . ? C22 C21 C26 121.1(9) . . ? C20 C21 C26 121.3(8) . . ? C23 C22 C21 123.4(9) . . ? C22 C23 C24 117.3(8) . . ? C22 C23 C27 123.4(9) . . ? C24 C23 C27 119.2(8) . . ? C25 C24 C23 122.3(8) . . ? C24 C25 C20 116.7(9) . . ? C24 C25 C28 121.7(8) . . ? C20 C25 C28 121.6(8) . . ? C6 N1 C9 107.2(7) . . ? C6 N1 C20 126.6(7) . . ? C9 N1 C20 126.0(7) . . ? C6 N2 C8 108.7(7) . . ? C6 N2 C10 124.1(7) . . ? C8 N2 C10 126.9(8) . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 27.58 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.726 _refine_diff_density_min -0.653 _refine_diff_density_rms 0.194