# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 188/202 data_GLOBAL # 1. SUBMISSION DETAILS _publ_contact_author_name 'Gleiter, Rolf' _publ_contact_author_address ; Organisch-Chemisches Institut Universitat Heidelberg Im Neuenheimer Feld 270 D-69120 Heidelberg Germany ; _publ_contact_author_phone '049 6221 54- 8400' _publ_contact_author_fax '049 6221 54- 4205' _publ_contact_author_email 'rolf.gleiter@urz.uni-heidelberg.de' _publ_requested_journal 'J. Chem. Soc. Perkin Trans. II' _publ_requested_coeditor_name ? _publ_contact_letter ; paper to be published in the Journal of Chemical Society Perkin Trans. II ; #======================================================================= # 3. TITLE AND AUTHOR LIST _publ_section_title ; N,N'-Bridged-1,10-Diazabicyclooctadeca-5,14-diynes. - Syntheses and Properties ; loop_ _publ_author_name _publ_author_address 'von Hirschheydt, Thomas' ; Organisch-Chemisches Institut Universit\"at Heidelberg Im Neuenheimer Feld 270 69120 Heidelberg Bundesrepublik Deutschland ; 'Wolfart, Volker' ; Organisch-Chemisches Institut Universit\"at Heidelberg Im Neuenheimer Feld 270 69120 Heidelberg Bundesrepublik Deutschland ; 'Gleiter, Rolf' ; Organisch-Chemisches Institut Universit\"at Heidelberg Im Neuenheimer Feld 270 69120 Heidelberg Bundesrepublik Deutschland ; 'Irngartinger, Hermann' ; Organisch-Chemisches Institut Universit\"at Heidelberg Im Neuenheimer Feld 270 69120 Heidelberg Bundesrepublik Deutschland ; 'Oeser, Thomas' ; Organisch-Chemisches Institut Universit\"at Heidelberg Im Neuenheimer Feld 270 69120 Heidelberg Bundesrepublik Deutschland ; 'Rominger, Frank' ; Organisch-Chemisches Institut Universit\"at Heidelberg Im Neuenheimer Feld 270 69120 Heidelberg Bundesrepublik Deutschland ; 'Eisentr\"ager, Frank' ; Organisch-Chemisches Institut Universit\"at Heidelberg Im Neuenheimer Feld 270 69120 Heidelberg Bundesrepublik Deutschland ; #======================================================================= _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38.' data_th18 _audit_creation_method SHELXL-97 _chemical_name_systematic ; (34) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H28 N2' _chemical_formula_weight 272.42 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 P2(1)2(1)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' _cell_length_a 10.7545(2) _cell_length_b 11.0123(2) _cell_length_c 6.84330(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 810.46(2) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description polyhedron _exptl_crystal_colour colorless _exptl_crystal_size_max .32 _exptl_crystal_size_mid .24 _exptl_crystal_size_min .16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.116 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 300 _exptl_absorpt_coefficient_mu 0.065 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38.' _exptl_absorpt_correction_T_min 0.58 _exptl_absorpt_correction_T_max 1.00 _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6016 _diffrn_reflns_av_R_equivalents 0.0278 _diffrn_reflns_av_sigmaI/netI 0.0266 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.65 _diffrn_reflns_theta_max 25.36 _reflns_number_total 1408 _reflns_number_gt 1244 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0449P)^2^+0.0092P] 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 ride _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.058(7) _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 -2(3) _refine_ls_number_reflns 1408 _refine_ls_number_parameters 92 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0394 _refine_ls_R_factor_gt 0.0305 _refine_ls_wR_factor_ref 0.0747 _refine_ls_wR_factor_gt 0.0711 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N -0.10882(8) -0.90365(8) -0.41030(15) 0.0314(3) Uani 1 1 d . . . C5 C 0.14675(11) -0.88536(12) -0.0658(2) 0.0403(4) Uani 1 1 d . . . C8 C -0.22280(10) -0.97614(11) -0.41590(19) 0.0344(3) Uani 1 1 d . . . H8A H -0.2007 -1.0615 -0.4451 0.041 Uiso 1 1 calc R . . H8B H -0.2760 -0.9463 -0.5237 0.041 Uiso 1 1 calc R . . C9 C -0.29691(11) -0.97250(12) -0.22698(19) 0.0395(4) Uani 1 1 d . . . H9A H -0.3659 -1.0318 -0.2355 0.047 Uiso 1 1 calc R . . H9B H -0.3338 -0.8907 -0.2114 0.047 Uiso 1 1 calc R . . C4 C 0.08168(12) -0.79951(13) -0.0960(2) 0.0439(4) Uani 1 1 d . . . C1 C -0.13986(12) -0.77349(11) -0.4207(2) 0.0448(4) Uani 1 1 d . . . H1A H -0.2137 -0.7584 -0.3378 0.054 Uiso 1 1 calc R . . H1B H -0.1630 -0.7536 -0.5570 0.054 Uiso 1 1 calc R . . C7 C -0.02686(11) -0.93564(12) -0.57390(19) 0.0387(4) Uani 1 1 d . . . H7A H 0.0433 -0.8775 -0.5755 0.046 Uiso 1 1 calc R . . H7B H -0.0739 -0.9241 -0.6969 0.046 Uiso 1 1 calc R . . C3 C -0.00080(15) -0.69763(13) -0.1412(2) 0.0560(4) Uani 1 1 d . . . H3A H 0.0406 -0.6212 -0.1015 0.067 Uiso 1 1 calc R . . H3B H -0.0776 -0.7058 -0.0625 0.067 Uiso 1 1 calc R . . C2 C -0.03664(13) -0.68823(12) -0.3570(2) 0.0530(4) Uani 1 1 d . . . H2A H -0.0629 -0.6038 -0.3844 0.064 Uiso 1 1 calc R . . H2B H 0.0380 -0.7050 -0.4372 0.064 Uiso 1 1 calc R . . C6 C 0.21791(12) -0.99844(12) -0.04658(18) 0.0416(3) Uani 1 1 d . . . H6A H 0.1595 -1.0664 -0.0232 0.050 Uiso 1 1 calc R . . H6B H 0.2731 -0.9921 0.0688 0.050 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 0.0286(5) 0.0289(6) 0.0368(6) 0.0001(5) -0.0051(5) -0.0004(4) C5 0.0386(7) 0.0450(8) 0.0372(8) -0.0055(7) -0.0066(7) -0.0046(7) C8 0.0291(6) 0.0346(7) 0.0395(7) -0.0044(6) -0.0047(6) -0.0002(5) C9 0.0337(7) 0.0361(7) 0.0487(8) -0.0069(6) 0.0034(6) 0.0022(6) C4 0.0401(7) 0.0424(8) 0.0494(9) -0.0128(7) -0.0083(7) -0.0021(7) C1 0.0405(7) 0.0319(7) 0.0621(10) 0.0056(7) -0.0128(8) 0.0026(6) C7 0.0341(7) 0.0503(8) 0.0318(7) 0.0096(6) -0.0046(6) -0.0002(6) C3 0.0480(7) 0.0371(8) 0.0830(12) -0.0199(8) -0.0169(9) 0.0045(7) C2 0.0466(8) 0.0267(7) 0.0858(12) 0.0060(7) -0.0163(8) 0.0000(6) C6 0.0441(7) 0.0444(8) 0.0364(8) 0.0055(6) -0.0086(6) -0.0006(7) _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 C8 1.4633(15) . ? N1 C7 1.4679(15) . ? N1 C1 1.4734(15) . ? C5 C4 1.1943(18) . ? C5 C6 1.4675(18) . ? C8 C9 1.5193(16) . ? C9 C6 1.5324(17) 2_535 ? C4 C3 1.463(2) . ? C1 C2 1.5179(18) . ? C7 C7 1.531(3) 2_535 ? C3 C2 1.529(2) . ? C6 C9 1.5324(17) 2_535 ? 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 C8 N1 C7 110.62(9) . . ? C8 N1 C1 109.86(9) . . ? C7 N1 C1 109.43(10) . . ? C4 C5 C6 173.15(13) . . ? N1 C8 C9 113.75(10) . . ? C8 C9 C6 112.90(10) . 2_535 ? C5 C4 C3 177.12(14) . . ? N1 C1 C2 114.97(10) . . ? N1 C7 C7 116.67(8) . 2_535 ? C4 C3 C2 114.13(12) . . ? C1 C2 C3 114.83(13) . . ? C5 C6 C9 113.20(10) . 2_535 ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 25.36 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.101 _refine_diff_density_min -0.107 _refine_diff_density_rms 0.025 data_th16 _audit_creation_method SHELXL-97 _chemical_name_systematic ; (35) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H35.50 N2 O4.06' _chemical_formula_weight 356.91 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.1299(9) _cell_length_b 12.4995(10) _cell_length_c 15.5200(13) _cell_angle_alpha 101.3480(10) _cell_angle_beta 93.019(2) _cell_angle_gamma 102.1370(10) _cell_volume 2059.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description irregular _exptl_crystal_colour colorless _exptl_crystal_size_max .31 _exptl_crystal_size_mid .20 _exptl_crystal_size_min .06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.151 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38.' _exptl_absorpt_correction_T_min 0.58 _exptl_absorpt_correction_T_max 1.00 _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15475 _diffrn_reflns_av_R_equivalents 0.0581 _diffrn_reflns_av_sigmaI/netI 0.1010 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.34 _diffrn_reflns_theta_max 25.61 _reflns_number_total 6862 _reflns_number_gt 3358 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0671P)^2^+0.3960P] 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 ride _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6862 _refine_ls_number_parameters 491 _refine_ls_number_restraints 55 _refine_ls_R_factor_all 0.1538 _refine_ls_R_factor_gt 0.0613 _refine_ls_wR_factor_ref 0.1659 _refine_ls_wR_factor_gt 0.1279 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.007 _refine_ls_shift/su_max 2.691 _refine_ls_shift/su_mean 0.068 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 0.6837(2) -0.1982(2) 0.48876(16) 0.0280(6) Uani 1 1 d . . . C2 C 0.7694(3) -0.2687(3) 0.4542(2) 0.0367(9) Uani 1 1 d . . . H2A H 0.7829 -0.2611 0.3930 0.044 Uiso 1 1 calc R . . H2B H 0.7304 -0.3481 0.4523 0.044 Uiso 1 1 calc R . . C3 C 0.8940(3) -0.2385(3) 0.5091(2) 0.0403(9) Uani 1 1 d . . . H3A H 0.8912 -0.2858 0.5535 0.048 Uiso 1 1 calc R . . H3B H 0.9100 -0.1594 0.5412 0.048 Uiso 1 1 calc R . . C4 C 1.0003(3) -0.2548(3) 0.4523(2) 0.0370(9) Uani 1 1 d . . . H4A H 1.0762 -0.2453 0.4919 0.044 Uiso 1 1 calc R . . H4B H 0.9806 -0.3325 0.4170 0.044 Uiso 1 1 calc R . . C5 C 1.0256(3) -0.1769(3) 0.3918(2) 0.0343(9) Uani 1 1 d . . . C6 C 1.0493(3) -0.1182(3) 0.3403(2) 0.0360(9) Uani 1 1 d . . . C7 C 1.0881(3) -0.0517(3) 0.2739(2) 0.0404(9) Uani 1 1 d . . . H7A H 1.0857 -0.1038 0.2165 0.048 Uiso 1 1 calc R . . H7B H 1.1749 -0.0105 0.2911 0.048 Uiso 1 1 calc R . . C8 C 1.0108(3) 0.0327(3) 0.2608(2) 0.0352(9) Uani 1 1 d . . . H8A H 1.0156 0.0869 0.3174 0.042 Uiso 1 1 calc R . . H8B H 1.0472 0.0750 0.2172 0.042 Uiso 1 1 calc R . . C9 C 0.8750(3) -0.0199(3) 0.2292(2) 0.0353(9) Uani 1 1 d . . . H9A H 0.8631 -0.0285 0.1643 0.042 Uiso 1 1 calc R . . H9B H 0.8540 -0.0957 0.2422 0.042 Uiso 1 1 calc R . . N10 N 0.7892(2) 0.0458(2) 0.27027(16) 0.0297(7) Uani 1 1 d . . . C11 C 0.6656(3) 0.0032(3) 0.2198(2) 0.0327(8) Uani 1 1 d . . . H11A H 0.6361 -0.0766 0.2221 0.039 Uiso 1 1 calc R . . H11B H 0.6741 0.0069 0.1572 0.039 Uiso 1 1 calc R . . C12 C 0.5676(3) 0.0666(3) 0.2530(2) 0.0373(9) Uani 1 1 d . . . H12A H 0.5748 0.1337 0.2269 0.045 Uiso 1 1 calc R . . H12B H 0.5825 0.0922 0.3179 0.045 Uiso 1 1 calc R . . C13 C 0.4363(3) -0.0073(3) 0.2284(2) 0.0405(9) Uani 1 1 d . . . H13A H 0.3764 0.0414 0.2304 0.049 Uiso 1 1 calc R . . H13B H 0.4301 -0.0510 0.1671 0.049 Uiso 1 1 calc R . . C14 C 0.4037(3) -0.0846(3) 0.2879(2) 0.0356(9) Uani 1 1 d . . . C15 C 0.3787(3) -0.1422(3) 0.3400(2) 0.0343(9) Uani 1 1 d . . . C16 C 0.3489(3) -0.2098(3) 0.4076(2) 0.0371(9) Uani 1 1 d . . . H16A H 0.3254 -0.2901 0.3784 0.045 Uiso 1 1 calc R . . H16B H 0.2770 -0.1901 0.4366 0.045 Uiso 1 1 calc R . . C17 C 0.4576(3) -0.1911(3) 0.4784(2) 0.0362(9) Uani 1 1 d . . . H17A H 0.4935 -0.1098 0.4980 0.043 Uiso 1 1 calc R . . H17B H 0.4268 -0.2195 0.5302 0.043 Uiso 1 1 calc R . . C18 C 0.5583(3) -0.2501(3) 0.4440(2) 0.0316(8) Uani 1 1 d . . . H18A H 0.5360 -0.3288 0.4508 0.038 Uiso 1 1 calc R . . H18B H 0.5602 -0.2513 0.3801 0.038 Uiso 1 1 calc R . . C19 C 0.7271(3) -0.0826(3) 0.4759(2) 0.0320(8) Uani 1 1 d . . . H19A H 0.8154 -0.0558 0.4985 0.038 Uiso 1 1 calc R . . H19B H 0.6806 -0.0334 0.5114 0.038 Uiso 1 1 calc R . . C20 C 0.7127(3) -0.0712(3) 0.3803(2) 0.0398(9) Uani 1 1 d . . . H20A H 0.7411 -0.1328 0.3425 0.048 Uiso 1 1 calc R . . H20B H 0.6240 -0.0798 0.3621 0.048 Uiso 1 1 calc R . . C21 C 0.7837(3) 0.0392(3) 0.3647(2) 0.0332(8) Uani 1 1 d . . . H21A H 0.7455 0.0995 0.3945 0.040 Uiso 1 1 calc R . . H21B H 0.8692 0.0538 0.3928 0.040 Uiso 1 1 calc R . . N31 N 0.7603(2) 0.5496(2) 0.15681(16) 0.0288(6) Uani 1 1 d . . . C32 C 0.8789(3) 0.6058(3) 0.2088(2) 0.0368(9) Uani 1 1 d . . . H32A H 0.8656 0.6181 0.2722 0.044 Uiso 1 1 calc R . . H32B H 0.9066 0.6803 0.1944 0.044 Uiso 1 1 calc R . . C33 C 0.9817(3) 0.5427(3) 0.1940(2) 0.0440(10) Uani 1 1 d . . . H33A H 0.9666 0.4951 0.1338 0.053 Uiso 1 1 calc R . . H33B H 0.9793 0.4929 0.2365 0.053 Uiso 1 1 calc R . . C34 C 1.1104(3) 0.6203(3) 0.2049(2) 0.0414(9) Uani 1 1 d . . . H34A H 1.1205 0.6754 0.2616 0.050 Uiso 1 1 calc R . . H34B H 1.1731 0.5752 0.2080 0.050 Uiso 1 1 calc R . . C35 C 1.1341(3) 0.6813(3) 0.1331(3) 0.0393(9) Uani 1 1 d . . . C36 C 1.1573(3) 0.7313(3) 0.0754(3) 0.0417(9) Uani 1 1 d . . . C37 C 1.1924(3) 0.7948(3) 0.0068(2) 0.0460(10) Uani 1 1 d . . . H37A H 1.2639 0.7710 -0.0199 0.055 Uiso 1 1 calc R . . H37B H 1.2194 0.8752 0.0352 0.055 Uiso 1 1 calc R . . C38 C 1.0900(3) 0.7809(3) -0.0667(2) 0.0403(9) Uani 1 1 d . . . H38A H 1.0596 0.7002 -0.0932 0.048 Uiso 1 1 calc R . . H38B H 1.1249 0.8182 -0.1134 0.048 Uiso 1 1 calc R . . C39 C 0.9810(3) 0.8295(3) -0.0350(2) 0.0354(9) Uani 1 1 d . . . H39A H 0.9794 0.8323 0.0291 0.042 Uiso 1 1 calc R . . H39B H 0.9941 0.9073 -0.0437 0.042 Uiso 1 1 calc R . . N40 N 0.8596(2) 0.7652(2) -0.08075(17) 0.0308(7) Uani 1 1 d . . . C41 C 0.7664(3) 0.8319(3) -0.0581(2) 0.0344(8) Uani 1 1 d . . . H41A H 0.7957 0.9065 -0.0720 0.041 Uiso 1 1 calc R . . H41B H 0.7608 0.8436 0.0064 0.041 Uiso 1 1 calc R . . C42 C 0.6372(3) 0.7807(3) -0.1051(2) 0.0395(9) Uani 1 1 d . . . H42A H 0.6223 0.6981 -0.1153 0.047 Uiso 1 1 calc R . . H42B H 0.6326 0.8013 -0.1634 0.047 Uiso 1 1 calc R . . C43 C 0.5360(3) 0.8199(3) -0.0523(2) 0.0428(9) Uani 1 1 d . . . H43A H 0.5615 0.9019 -0.0296 0.051 Uiso 1 1 calc R . . H43B H 0.4592 0.8044 -0.0922 0.051 Uiso 1 1 calc R . . C44 C 0.5107(3) 0.7647(3) 0.0223(2) 0.0368(9) Uani 1 1 d . . . C45 C 0.4874(3) 0.7145(3) 0.0793(2) 0.0337(9) Uani 1 1 d . . . C46 C 0.4560(3) 0.6467(3) 0.1464(2) 0.0373(9) Uani 1 1 d . . . H46A H 0.3676 0.6084 0.1351 0.045 Uiso 1 1 calc R . . H46B H 0.4687 0.6971 0.2055 0.045 Uiso 1 1 calc R . . C47 C 0.5341(3) 0.5583(3) 0.1466(2) 0.0346(8) Uani 1 1 d . . . H47A H 0.4945 0.5023 0.1796 0.042 Uiso 1 1 calc R . . H47B H 0.5369 0.5187 0.0851 0.042 Uiso 1 1 calc R . . C48 C 0.6655(3) 0.6114(3) 0.1887(2) 0.0329(8) Uani 1 1 d . . . H48A H 0.6889 0.6880 0.1776 0.039 Uiso 1 1 calc R . . H48B H 0.6663 0.6182 0.2533 0.039 Uiso 1 1 calc R . . C49 C 0.7698(3) 0.5424(3) 0.0612(2) 0.0324(8) Uani 1 1 d . . . H49A H 0.6929 0.4937 0.0280 0.039 Uiso 1 1 calc R . . H49B H 0.8389 0.5069 0.0438 0.039 Uiso 1 1 calc R . . C50 C 0.7908(4) 0.6561(3) 0.0352(2) 0.0528(11) Uani 1 1 d . . . H50A H 0.7147 0.6849 0.0418 0.063 Uiso 1 1 calc R . . H50B H 0.8576 0.7093 0.0765 0.063 Uiso 1 1 calc R . . C51 C 0.8246(3) 0.6532(3) -0.0576(2) 0.0375(9) Uani 1 1 d . . . H51A H 0.8946 0.6160 -0.0662 0.045 Uiso 1 1 calc R . . H51B H 0.7536 0.6070 -0.0990 0.045 Uiso 1 1 calc R . . O1 O 0.8621(2) 0.6874(2) -0.26386(15) 0.0430(7) Uani 1 1 d D . . H1C H 0.815(3) 0.627(2) -0.292(2) 0.065 Uiso 1 1 d D . . H1D H 0.870(3) 0.714(3) -0.2084(15) 0.065 Uiso 1 1 d D . . O2 O 0.8860(2) 0.2810(2) 0.29992(18) 0.0469(7) Uani 1 1 d D . . H2C H 0.962(2) 0.298(3) 0.286(2) 0.070 Uiso 1 1 d D . . H2D H 0.850(3) 0.2099(19) 0.290(3) 0.070 Uiso 1 1 d D . . O3 O 0.6743(2) -0.2151(2) 0.66551(17) 0.0507(7) Uani 1 1 d D . . H3C H 0.732(3) -0.250(3) 0.676(3) 0.076 Uiso 1 1 d D . . H3D H 0.672(4) -0.210(3) 0.6096(16) 0.076 Uiso 1 1 d D . . O4 O 0.6921(2) 0.3459(2) 0.21124(19) 0.0555(8) Uani 1 1 d D . . H4C H 0.755(3) 0.333(3) 0.239(3) 0.083 Uiso 1 1 d D . . H4D H 0.723(3) 0.409(2) 0.195(3) 0.083 Uiso 1 1 d D . . O5 O 0.4694(3) -0.3876(3) 0.6632(2) 0.0735(9) Uani 1 1 d D . . H5C H 0.421(4) -0.417(4) 0.618(2) 0.110 Uiso 1 1 d D . . H5D H 0.521(4) -0.325(3) 0.672(3) 0.110 Uiso 1 1 d D . . O6 O 0.6656(3) 0.4999(3) -0.3298(3) 0.1006(12) Uani 1 1 d D . . H6C H 0.712(5) 0.500(5) -0.379(3) 0.151 Uiso 1 1 d D . . O7 O 1.3201(7) 0.5404(4) 0.5060(3) 0.167(4) Uani 0.927(14) 1 d P . . O8 O 1.0843(6) 0.5406(4) 0.5610(3) 0.133(3) Uani 0.868(10) 1 d P . . O9 O 1.212(2) 0.5743(12) 0.5411(10) 0.116(8) Uiso 0.309(14) 1 d P . . 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 0.0265(15) 0.0288(16) 0.0295(16) 0.0072(13) 0.0020(12) 0.0070(12) C2 0.034(2) 0.041(2) 0.036(2) 0.0096(17) -0.0012(17) 0.0119(17) C3 0.029(2) 0.057(2) 0.036(2) 0.0094(19) -0.0001(17) 0.0131(17) C4 0.032(2) 0.043(2) 0.038(2) 0.0113(18) -0.0036(16) 0.0115(17) C5 0.025(2) 0.039(2) 0.038(2) 0.0038(19) -0.0019(16) 0.0111(16) C6 0.0240(19) 0.040(2) 0.043(2) 0.007(2) -0.0024(17) 0.0083(16) C7 0.029(2) 0.045(2) 0.050(2) 0.0136(19) 0.0118(18) 0.0082(17) C8 0.030(2) 0.036(2) 0.039(2) 0.0090(17) 0.0087(16) 0.0050(16) C9 0.036(2) 0.034(2) 0.036(2) 0.0060(17) 0.0037(17) 0.0095(16) N10 0.0254(15) 0.0375(17) 0.0261(17) 0.0082(13) 0.0003(12) 0.0062(13) C11 0.032(2) 0.044(2) 0.024(2) 0.0126(17) 0.0017(16) 0.0095(17) C12 0.038(2) 0.039(2) 0.039(2) 0.0149(17) 0.0021(17) 0.0124(17) C13 0.031(2) 0.051(2) 0.047(2) 0.023(2) 0.0052(17) 0.0153(18) C14 0.029(2) 0.040(2) 0.039(2) 0.0077(19) 0.0022(17) 0.0122(17) C15 0.0214(19) 0.038(2) 0.044(2) 0.0063(19) 0.0024(17) 0.0110(16) C16 0.028(2) 0.039(2) 0.047(2) 0.0159(18) 0.0054(17) 0.0087(16) C17 0.032(2) 0.044(2) 0.036(2) 0.0148(18) 0.0092(17) 0.0088(17) C18 0.0259(19) 0.033(2) 0.037(2) 0.0100(16) 0.0013(16) 0.0069(15) C19 0.0275(19) 0.036(2) 0.032(2) 0.0098(17) 0.0014(15) 0.0046(15) C20 0.039(2) 0.046(2) 0.033(2) 0.0173(18) -0.0047(17) 0.0000(17) C21 0.034(2) 0.039(2) 0.027(2) 0.0123(16) -0.0014(16) 0.0035(16) N31 0.0299(16) 0.0296(16) 0.0258(16) 0.0048(13) 0.0019(13) 0.0059(12) C32 0.033(2) 0.039(2) 0.037(2) 0.0012(17) -0.0043(16) 0.0131(17) C33 0.038(2) 0.045(2) 0.055(3) 0.0170(19) 0.0028(18) 0.0167(18) C34 0.031(2) 0.054(2) 0.042(2) 0.0077(19) 0.0030(17) 0.0197(18) C35 0.026(2) 0.049(2) 0.044(3) 0.004(2) 0.0040(18) 0.0174(17) C36 0.031(2) 0.055(3) 0.042(2) 0.008(2) 0.0048(18) 0.0177(18) C37 0.029(2) 0.056(3) 0.055(3) 0.018(2) 0.0038(19) 0.0082(18) C38 0.034(2) 0.048(2) 0.041(2) 0.0102(18) 0.0080(17) 0.0108(17) C39 0.0275(19) 0.038(2) 0.038(2) 0.0029(17) 0.0018(16) 0.0073(16) N40 0.0288(16) 0.0294(16) 0.0369(17) 0.0111(13) 0.0061(13) 0.0081(13) C41 0.034(2) 0.033(2) 0.040(2) 0.0132(17) 0.0051(17) 0.0110(16) C42 0.035(2) 0.051(2) 0.035(2) 0.0155(18) 0.0013(17) 0.0118(18) C43 0.032(2) 0.058(2) 0.046(2) 0.024(2) 0.0058(18) 0.0171(18) C44 0.026(2) 0.047(2) 0.040(2) 0.012(2) 0.0023(17) 0.0122(17) C45 0.0224(19) 0.044(2) 0.034(2) 0.0025(19) 0.0022(16) 0.0111(16) C46 0.0271(19) 0.051(2) 0.034(2) 0.0118(18) 0.0067(16) 0.0071(17) C47 0.032(2) 0.036(2) 0.034(2) 0.0051(17) 0.0005(16) 0.0062(16) C48 0.031(2) 0.040(2) 0.027(2) 0.0030(16) 0.0057(16) 0.0105(16) C49 0.0317(19) 0.039(2) 0.028(2) 0.0082(17) 0.0069(15) 0.0085(16) C50 0.073(3) 0.053(3) 0.043(2) 0.020(2) 0.023(2) 0.023(2) C51 0.035(2) 0.042(2) 0.039(2) 0.0120(18) 0.0082(17) 0.0130(17) O1 0.0460(16) 0.0441(17) 0.0320(15) 0.0049(13) -0.0040(13) -0.0002(12) O2 0.0359(15) 0.0465(16) 0.0603(18) 0.0199(15) 0.0105(13) 0.0046(13) O3 0.0554(18) 0.0696(19) 0.0375(16) 0.0248(15) 0.0094(14) 0.0231(14) O4 0.0463(17) 0.0530(18) 0.076(2) 0.0375(16) 0.0032(15) 0.0093(14) O5 0.064(2) 0.081(2) 0.074(2) 0.030(2) 0.0021(17) -0.0003(17) O6 0.104(3) 0.056(2) 0.131(3) 0.018(2) -0.025(2) 0.0063(19) O7 0.213(8) 0.135(5) 0.117(5) 0.054(4) -0.022(4) -0.055(5) O8 0.195(7) 0.096(4) 0.106(4) 0.013(3) 0.027(3) 0.034(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C18 1.480(4) . ? N1 C19 1.481(4) . ? N1 C2 1.482(4) . ? C2 C3 1.523(4) . ? C3 C4 1.536(4) . ? C4 C5 1.477(5) . ? C5 C6 1.191(4) . ? C6 C7 1.474(5) . ? C7 C8 1.530(4) . ? C8 C9 1.528(4) . ? C9 N10 1.477(4) . ? N10 C11 1.485(4) . ? N10 C21 1.488(4) . ? C11 C12 1.531(4) . ? C12 C13 1.539(4) . ? C13 C14 1.469(5) . ? C14 C15 1.192(4) . ? C15 C16 1.481(5) . ? C16 C17 1.538(4) . ? C17 C18 1.529(4) . ? C19 C20 1.520(4) . ? C20 C21 1.511(4) . ? N31 C32 1.471(4) . ? N31 C49 1.480(4) . ? N31 C48 1.483(4) . ? C32 C33 1.523(4) . ? C33 C34 1.532(4) . ? C34 C35 1.475(5) . ? C35 C36 1.199(5) . ? C36 C37 1.469(5) . ? C37 C38 1.527(4) . ? C38 C39 1.529(4) . ? C39 N40 1.481(4) . ? N40 C41 1.476(4) . ? N40 C51 1.491(4) . ? C41 C42 1.526(4) . ? C42 C43 1.533(4) . ? C43 C44 1.471(5) . ? C44 C45 1.190(4) . ? C45 C46 1.479(5) . ? C46 C47 1.544(4) . ? C47 C48 1.525(4) . ? C49 C50 1.527(4) . ? C50 C51 1.503(4) . ? O7 O9 1.455(17) . ? O8 O9 1.46(2) . ? 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 C18 N1 C19 111.6(2) . . ? C18 N1 C2 108.9(2) . . ? C19 N1 C2 110.4(2) . . ? N1 C2 C3 113.5(3) . . ? C2 C3 C4 112.3(3) . . ? C5 C4 C3 114.4(3) . . ? C6 C5 C4 176.4(3) . . ? C5 C6 C7 174.3(3) . . ? C6 C7 C8 115.6(3) . . ? C9 C8 C7 114.2(3) . . ? N10 C9 C8 113.7(3) . . ? C9 N10 C11 108.8(2) . . ? C9 N10 C21 110.5(2) . . ? C11 N10 C21 111.4(2) . . ? N10 C11 C12 114.7(3) . . ? C11 C12 C13 111.6(3) . . ? C14 C13 C12 112.4(3) . . ? C15 C14 C13 176.3(4) . . ? C14 C15 C16 177.7(4) . . ? C15 C16 C17 112.5(3) . . ? C18 C17 C16 112.1(3) . . ? N1 C18 C17 114.7(3) . . ? N1 C19 C20 114.2(3) . . ? C21 C20 C19 113.6(3) . . ? N10 C21 C20 115.0(3) . . ? C32 N31 C49 111.4(2) . . ? C32 N31 C48 108.5(2) . . ? C49 N31 C48 111.5(2) . . ? N31 C32 C33 115.0(3) . . ? C32 C33 C34 113.1(3) . . ? C35 C34 C33 113.9(3) . . ? C36 C35 C34 178.0(3) . . ? C35 C36 C37 177.0(4) . . ? C36 C37 C38 114.7(3) . . ? C37 C38 C39 113.4(3) . . ? N40 C39 C38 114.0(3) . . ? C41 N40 C39 108.7(2) . . ? C41 N40 C51 111.6(2) . . ? C39 N40 C51 111.3(2) . . ? N40 C41 C42 115.3(3) . . ? C41 C42 C43 112.5(3) . . ? C44 C43 C42 112.8(3) . . ? C45 C44 C43 176.3(4) . . ? C44 C45 C46 177.0(4) . . ? C45 C46 C47 112.9(3) . . ? C48 C47 C46 111.7(3) . . ? N31 C48 C47 115.2(3) . . ? N31 C49 C50 113.4(3) . . ? C51 C50 C49 114.0(3) . . ? N40 C51 C50 114.7(3) . . ? O8 O9 O7 147.8(11) . . ? _diffrn_measured_fraction_theta_max 0.882 _diffrn_reflns_theta_full 25.61 _diffrn_measured_fraction_theta_full 0.882 _refine_diff_density_max 0.437 _refine_diff_density_min -0.261 _refine_diff_density_rms 0.046 data_739hbi _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,10-Diazabicyclo[8.8.5]tricosa-5,14-diyne (37) ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H34 N2' _chemical_formula_weight 314.50 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 30.666(14) _cell_length_b 12.356(2) _cell_length_c 15.188(7) _cell_angle_alpha 90.00 _cell_angle_beta 91.13(3) _cell_angle_gamma 90.00 _cell_volume 5754(4) _cell_formula_units_Z 12 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.50 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.089 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2088 _exptl_absorpt_coefficient_mu 0.063 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9692 _exptl_absorpt_correction_T_max 0.9692 _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type NONIUS_CAD4 _diffrn_measurement_method \w2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 1 _diffrn_reflns_number 7036 _diffrn_reflns_av_R_equivalents 0.0125 _diffrn_reflns_av_sigmaI/netI 0.0278 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 40 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 27.97 _reflns_number_total 6913 _reflns_number_gt 4646 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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 w=1/[\s^2^(Fo^2^)+(0.0804P)^2^+2.0764P] 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 ride _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6913 _refine_ls_number_parameters 366 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0910 _refine_ls_R_factor_gt 0.0499 _refine_ls_wR_factor_ref 0.1515 _refine_ls_wR_factor_gt 0.1331 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.24159(4) 0.48046(9) 0.13261(7) 0.0349(3) Uani 1 d . . . N10 N 0.39957(4) 0.56073(10) -0.00338(8) 0.0380(3) Uani 1 d . . . C2 C 0.24537(5) 0.39717(12) 0.20089(9) 0.0390(3) Uani 1 d . . . H2A H 0.2340 0.3285 0.1777 0.047 Uiso 1 calc R . . H2B H 0.2277 0.4179 0.2512 0.047 Uiso 1 calc R . . C3 C 0.29237(5) 0.38208(12) 0.23133(9) 0.0387(3) Uani 1 d . . . H3A H 0.2934 0.3357 0.2837 0.046 Uiso 1 calc R . . H3B H 0.3049 0.4525 0.2475 0.046 Uiso 1 calc R . . C4 C 0.31940(4) 0.33073(12) 0.15895(9) 0.0390(3) Uani 1 d . . . H4A H 0.3163 0.2519 0.1624 0.047 Uiso 1 calc R . . H4B H 0.3074 0.3539 0.1017 0.047 Uiso 1 calc R . . C5 C 0.36582(5) 0.35747(12) 0.16305(9) 0.0385(3) Uani 1 d . . . C6 C 0.40299(5) 0.38437(12) 0.16100(9) 0.0421(3) Uani 1 d . . . C7 C 0.44856(5) 0.41919(15) 0.15806(11) 0.0522(4) Uani 1 d . . . H7A H 0.4649 0.3664 0.1236 0.063 Uiso 1 calc R . . H7B H 0.4608 0.4188 0.2181 0.063 Uiso 1 calc R . . C8 C 0.45526(5) 0.53121(14) 0.11852(11) 0.0488(4) Uani 1 d . . . H8A H 0.4367 0.5826 0.1496 0.059 Uiso 1 calc R . . H8B H 0.4856 0.5528 0.1295 0.059 Uiso 1 calc R . . C9 C 0.44543(5) 0.54123(14) 0.02038(10) 0.0458(4) Uani 1 d . . . H9A H 0.4629 0.6007 -0.0030 0.055 Uiso 1 calc R . . H9B H 0.4548 0.4745 -0.0085 0.055 Uiso 1 calc R . . C11 C 0.39175(5) 0.54158(14) -0.09783(10) 0.0477(4) Uani 1 d . . . H11A H 0.4137 0.5815 -0.1307 0.057 Uiso 1 calc R . . H11B H 0.3632 0.5717 -0.1143 0.057 Uiso 1 calc R . . C12 C 0.39290(5) 0.42450(15) -0.12647(10) 0.0506(4) Uani 1 d . . . H12A H 0.4228 0.3973 -0.1188 0.061 Uiso 1 calc R . . H12B H 0.3853 0.4206 -0.1894 0.061 Uiso 1 calc R . . C13 C 0.36226(5) 0.35123(13) -0.07631(10) 0.0469(4) Uani 1 d . . . H13A H 0.3640 0.2780 -0.1008 0.056 Uiso 1 calc R . . H13B H 0.3723 0.3476 -0.0147 0.056 Uiso 1 calc R . . C14 C 0.31667(5) 0.38602(12) -0.07886(9) 0.0418(3) Uani 1 d . . . C15 C 0.27945(5) 0.41362(12) -0.07676(9) 0.0398(3) Uani 1 d . . . C16 C 0.23342(5) 0.44361(13) -0.07473(9) 0.0426(3) Uani 1 d . . . H16A H 0.2196 0.4226 -0.1309 0.051 Uiso 1 calc R . . H16B H 0.2314 0.5225 -0.0700 0.051 Uiso 1 calc R . . C17 C 0.20742(4) 0.39286(12) 0.00049(9) 0.0395(3) Uani 1 d . . . H17A H 0.1785 0.3721 -0.0224 0.047 Uiso 1 calc R . . H17B H 0.2223 0.3268 0.0203 0.047 Uiso 1 calc R . . C18 C 0.20189(4) 0.46719(13) 0.07895(9) 0.0419(3) Uani 1 d . . . H18A H 0.1923 0.5384 0.0577 0.050 Uiso 1 calc R . . H18B H 0.1789 0.4382 0.1160 0.050 Uiso 1 calc R . . C19 C 0.24615(5) 0.59043(12) 0.16782(9) 0.0417(3) Uani 1 d . . . H19A H 0.2626 0.5880 0.2237 0.050 Uiso 1 calc R . . H19B H 0.2172 0.6201 0.1794 0.050 Uiso 1 calc R . . C20 C 0.26941(5) 0.66363(12) 0.10385(10) 0.0425(3) Uani 1 d . . . H20A H 0.2677 0.7385 0.1248 0.051 Uiso 1 calc R . . H20B H 0.2544 0.6600 0.0463 0.051 Uiso 1 calc R . . C21 C 0.31711(5) 0.63311(12) 0.09302(10) 0.0415(3) Uani 1 d . . . H21A H 0.3327 0.6454 0.1490 0.050 Uiso 1 calc R . . H21B H 0.3189 0.5557 0.0795 0.050 Uiso 1 calc R . . C22 C 0.33963(5) 0.69591(12) 0.02144(10) 0.0453(3) Uani 1 d . . . H22A H 0.3353 0.7735 0.0315 0.054 Uiso 1 calc R . . H22B H 0.3259 0.6778 -0.0355 0.054 Uiso 1 calc R . . C23 C 0.38826(5) 0.67329(12) 0.01709(11) 0.0468(4) Uani 1 d . . . H23A H 0.4008 0.7204 -0.0278 0.056 Uiso 1 calc R . . H23B H 0.4019 0.6926 0.0739 0.056 Uiso 1 calc R . . N1A N 0.41869(5) -0.00741(12) 0.18568(10) 0.0585(4) Uani 1 d . . . C2A C 0.38459(9) 0.0625(3) 0.2297(2) 0.0429(6) Uani 0.50 d P A 1 H2C H 0.3753 0.1206 0.1897 0.051 Uiso 0.50 calc PR A 1 H2D H 0.3590 0.0185 0.2433 0.051 Uiso 0.50 calc PR A 1 C2B C 0.40362(12) 0.0108(3) 0.2771(2) 0.0570(9) Uani 0.50 d P A 2 H2E H 0.3739 -0.0178 0.2801 0.068 Uiso 0.50 calc PR A 2 H2F H 0.4219 -0.0341 0.3162 0.068 Uiso 0.50 calc PR A 2 C3A C 0.40308(6) 0.1092(2) 0.31137(12) 0.0698(6) Uani 1 d . . . H3C H 0.4091 0.0498 0.3526 0.084 Uiso 1 calc R B 1 H3D H 0.3807 0.1550 0.3377 0.084 Uiso 1 calc R B 1 C4A C 0.44452(5) 0.17617(14) 0.30333(9) 0.0455(4) Uani 1 d . . . H4C H 0.4570 0.1620 0.2456 0.055 Uiso 1 calc R . . H4D H 0.4366 0.2530 0.3052 0.055 Uiso 1 calc R . . C5A C 0.47792(5) 0.15619(12) 0.37050(9) 0.0404(3) Uani 1 d . . . C6A C 0.50704(6) 0.13971(16) 0.42081(10) 0.0549(4) Uani 1 d . . . C7A C 0.53673(16) 0.1068(5) 0.4908(3) 0.0566(12) Uani 0.50 d P C 1 H7C H 0.5276 0.0360 0.5129 0.068 Uiso 0.50 calc PR C 1 H7D H 0.5347 0.1587 0.5394 0.068 Uiso 0.50 calc PR C 1 C8A C 0.58470(16) 0.0995(4) 0.4625(3) 0.0468(10) Uani 0.50 d P . 1 H8C H 0.5908 0.1601 0.4230 0.056 Uiso 0.50 calc PR . 1 H8D H 0.6036 0.1075 0.5148 0.056 Uiso 0.50 calc PR . 1 C9A C 0.40371(14) -0.0051(3) 0.0835(3) 0.0493(9) Uani 0.50 d P . 1 H9C H 0.4175 -0.0655 0.0530 0.059 Uiso 0.50 calc PR . 1 H9D H 0.3721 -0.0156 0.0793 0.059 Uiso 0.50 calc PR . 1 C19A C 0.43113(15) -0.1254(4) 0.1823(3) 0.0590(11) Uani 0.50 d P A 1 H19C H 0.4041 -0.1667 0.1890 0.071 Uiso 0.50 calc PR A 1 H19D H 0.4411 -0.1393 0.1224 0.071 Uiso 0.50 calc PR A 1 C20A C 0.46416(16) -0.1752(4) 0.2436(3) 0.0535(10) Uani 0.50 d P A 1 H20C H 0.4515 -0.1825 0.3021 0.064 Uiso 0.50 calc PR A 1 H20D H 0.4713 -0.2479 0.2225 0.064 Uiso 0.50 calc PR A 1 C7B C 0.54937(18) 0.1429(6) 0.4781(3) 0.0675(15) Uani 0.50 d P C 2 H7E H 0.5659 0.2081 0.4634 0.081 Uiso 0.50 calc PR C 2 H7F H 0.5415 0.1479 0.5402 0.081 Uiso 0.50 calc PR C 2 C8B C 0.57770(17) 0.0468(6) 0.4661(3) 0.0679(16) Uani 0.50 d P . 2 H8E H 0.5596 -0.0177 0.4744 0.082 Uiso 0.50 calc PR . 2 H8F H 0.5997 0.0473 0.5137 0.082 Uiso 0.50 calc PR . 2 C9B C 0.39873(12) 0.0331(4) 0.1195(3) 0.0584(10) Uani 0.50 d P . 2 H9E H 0.3881 0.1046 0.1370 0.070 Uiso 0.50 calc PR . 2 H9F H 0.3730 -0.0118 0.1074 0.070 Uiso 0.50 calc PR . 2 C19B C 0.41318(14) -0.1174(3) 0.2123(3) 0.0517(9) Uani 0.50 d P A 2 H19E H 0.3910 -0.1528 0.1751 0.062 Uiso 0.50 calc PR A 2 H19F H 0.4039 -0.1207 0.2736 0.062 Uiso 0.50 calc PR A 2 C20B C 0.45697(16) -0.1731(4) 0.2026(3) 0.0522(10) Uani 0.50 d P A 2 H20E H 0.4626 -0.1794 0.1395 0.063 Uiso 0.50 calc PR A 2 H20F H 0.4542 -0.2469 0.2256 0.063 Uiso 0.50 calc PR A 2 C21A C 0.5000 -0.1176(2) 0.2500 0.0726(9) Uani 1 d S . . H21C H 0.4982 -0.0708 0.3019 0.087 Uiso 0.50 calc PR D 1 H21D H 0.5018 -0.0708 0.1981 0.087 Uiso 0.50 calc PR D 1 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 0.0358(6) 0.0385(6) 0.0304(5) -0.0015(4) 0.0005(4) 0.0022(5) N10 0.0341(6) 0.0413(6) 0.0389(6) 0.0026(5) 0.0030(5) -0.0017(5) C2 0.0393(7) 0.0455(8) 0.0323(6) 0.0017(6) 0.0025(5) -0.0049(6) C3 0.0424(7) 0.0445(8) 0.0290(6) 0.0044(5) -0.0022(5) -0.0035(6) C4 0.0409(7) 0.0387(7) 0.0371(7) -0.0009(6) -0.0060(6) 0.0009(6) C5 0.0431(8) 0.0393(7) 0.0330(7) 0.0022(5) -0.0031(5) 0.0060(6) C6 0.0428(8) 0.0465(8) 0.0368(7) 0.0051(6) -0.0029(6) 0.0068(6) C7 0.0359(8) 0.0684(11) 0.0523(9) 0.0094(8) -0.0033(6) 0.0069(7) C8 0.0346(7) 0.0595(10) 0.0521(9) -0.0040(7) -0.0012(6) -0.0064(7) C9 0.0335(7) 0.0558(9) 0.0484(8) 0.0017(7) 0.0065(6) -0.0026(6) C11 0.0487(9) 0.0570(9) 0.0376(7) 0.0061(7) 0.0050(6) -0.0075(7) C12 0.0445(8) 0.0665(11) 0.0410(8) -0.0065(7) 0.0085(6) -0.0015(7) C13 0.0473(8) 0.0476(9) 0.0459(8) -0.0022(7) 0.0023(6) 0.0029(7) C14 0.0476(8) 0.0439(8) 0.0341(7) 0.0014(6) 0.0032(6) -0.0064(6) C15 0.0469(8) 0.0428(8) 0.0296(6) 0.0015(6) 0.0026(5) -0.0076(6) C16 0.0447(8) 0.0501(8) 0.0329(7) 0.0035(6) -0.0035(6) 0.0006(7) C17 0.0327(7) 0.0497(8) 0.0358(7) -0.0006(6) -0.0031(5) -0.0032(6) C18 0.0331(7) 0.0543(9) 0.0383(7) -0.0011(6) -0.0001(5) 0.0069(6) C19 0.0434(8) 0.0430(8) 0.0390(7) -0.0062(6) 0.0076(6) 0.0041(6) C20 0.0460(8) 0.0357(7) 0.0459(8) -0.0022(6) 0.0044(6) 0.0071(6) C21 0.0438(8) 0.0382(7) 0.0427(7) 0.0048(6) 0.0021(6) 0.0030(6) C22 0.0490(8) 0.0370(7) 0.0502(8) 0.0076(6) 0.0051(7) 0.0034(6) C23 0.0458(8) 0.0380(8) 0.0570(9) 0.0051(7) 0.0050(7) -0.0050(6) N1A 0.0754(10) 0.0459(8) 0.0546(8) -0.0108(6) 0.0145(7) 0.0000(7) C2A 0.0299(13) 0.0515(17) 0.0471(16) 0.0015(14) -0.0037(12) 0.0018(12) C2B 0.0499(19) 0.075(2) 0.0458(18) -0.0111(17) 0.0073(15) -0.0122(18) C3A 0.0459(10) 0.1110(17) 0.0529(10) -0.0279(11) 0.0146(8) -0.0145(10) C4A 0.0463(8) 0.0572(9) 0.0331(7) -0.0041(6) 0.0054(6) 0.0033(7) C5A 0.0458(8) 0.0413(8) 0.0345(7) -0.0008(6) 0.0084(6) -0.0032(6) C6A 0.0527(10) 0.0764(12) 0.0359(8) 0.0010(8) 0.0045(7) 0.0026(8) C7A 0.043(3) 0.086(4) 0.0400(19) 0.016(2) -0.0020(17) -0.017(2) C8A 0.038(2) 0.062(3) 0.0394(19) 0.0065(19) -0.0075(14) -0.0156(19) C9A 0.056(2) 0.052(2) 0.039(2) -0.0178(17) -0.0173(18) 0.0053(16) C19A 0.045(3) 0.059(2) 0.073(3) -0.020(2) -0.013(2) -0.008(2) C20A 0.062(3) 0.0370(19) 0.061(3) -0.007(2) -0.005(2) -0.0115(17) C7B 0.058(3) 0.108(5) 0.037(2) -0.010(3) -0.006(2) -0.026(3) C8B 0.044(2) 0.127(5) 0.033(2) 0.015(3) -0.0094(17) -0.016(3) C9B 0.0368(17) 0.100(4) 0.038(2) -0.004(2) -0.0076(15) 0.009(2) C19B 0.047(2) 0.0398(19) 0.068(3) 0.0006(18) -0.0085(18) -0.0055(18) C20B 0.065(3) 0.0331(17) 0.058(3) -0.005(2) -0.018(2) 0.0019(17) C21A 0.119(3) 0.0429(13) 0.0546(15) 0.000 -0.0375(15) 0.000 _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 C18 1.4609(18) . ? N1 C2 1.4640(18) . ? N1 C19 1.4660(18) . ? N10 C9 1.4651(19) . ? N10 C23 1.4681(19) . ? N10 C11 1.469(2) . ? C2 C3 1.516(2) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C3 C4 1.528(2) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C4 C5 1.462(2) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C5 C6 1.188(2) . ? C6 C7 1.464(2) . ? C7 C8 1.524(2) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C8 C9 1.520(2) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C11 C12 1.511(2) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C12 C13 1.520(2) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C13 C14 1.462(2) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C14 C15 1.192(2) . ? C15 C16 1.460(2) . ? C16 C17 1.540(2) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C17 C18 1.517(2) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C19 C20 1.516(2) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C20 C21 1.523(2) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C21 C22 1.513(2) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C22 C23 1.520(2) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? N1A C9B 1.269(4) . ? N1A C19B 1.429(4) . ? N1A C2B 1.490(4) . ? N1A C19A 1.508(5) . ? N1A C2A 1.521(3) . ? N1A C9A 1.610(4) . ? C2A C3A 1.471(3) . ? C2A H2C 0.9800 . ? C2A H2D 0.9800 . ? C2B C3A 1.322(4) . ? C2B C19B 1.891(6) . ? C2B H2E 0.9800 . ? C2B H2F 0.9800 . ? C3A C4A 1.523(2) . ? C3A H3C 0.9800 . ? C3A H3D 0.9800 . ? C4A C5A 1.453(2) . ? C4A H4C 0.9800 . ? C4A H4D 0.9800 . ? C5A C6A 1.181(2) . ? C6A C7A 1.444(5) . ? C6A C7B 1.549(5) . ? C7A C8A 1.543(7) . ? C7A H7C 0.9800 . ? C7A H7D 0.9800 . ? C8A C9A 1.514(7) 2_655 ? C8A H8C 0.9800 . ? C8A H8D 0.9800 . ? C9A C8A 1.514(7) 2_655 ? C9A H9C 0.9800 . ? C9A H9D 0.9800 . ? C19A C20A 1.494(6) . ? C19A H19C 0.9800 . ? C19A H19D 0.9800 . ? C20A C21A 1.311(5) . ? C20A H20C 0.9800 . ? C20A H20D 0.9800 . ? C7B C8B 1.484(10) . ? C7B H7E 0.9800 . ? C7B H7F 0.9800 . ? C8B C9B 1.510(7) 2_655 ? C8B H8E 0.9800 . ? C8B H8F 0.9800 . ? C9B C8B 1.510(7) 2_655 ? C9B H9E 0.9800 . ? C9B H9F 0.9800 . ? C19B C20B 1.519(6) . ? C19B H19E 0.9800 . ? C19B H19F 0.9800 . ? C20B C21A 1.641(5) . ? C20B H20E 0.9800 . ? C20B H20F 0.9800 . ? C21A C20A 1.311(5) 2_655 ? C21A C20B 1.641(5) 2_655 ? C21A H21C 0.9800 . ? C21A H21D 0.9800 . ? 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 C18 N1 C2 111.70(11) . . ? C18 N1 C19 112.32(11) . . ? C2 N1 C19 112.80(11) . . ? C9 N10 C23 109.46(12) . . ? C9 N10 C11 110.57(12) . . ? C23 N10 C11 108.95(12) . . ? N1 C2 C3 111.34(11) . . ? N1 C2 H2A 109.4 . . ? C3 C2 H2A 109.4 . . ? N1 C2 H2B 109.4 . . ? C3 C2 H2B 109.4 . . ? H2A C2 H2B 108.0 . . ? C2 C3 C4 110.95(11) . . ? C2 C3 H3A 109.4 . . ? C4 C3 H3A 109.4 . . ? C2 C3 H3B 109.4 . . ? C4 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? C5 C4 C3 114.66(12) . . ? C5 C4 H4A 108.6 . . ? C3 C4 H4A 108.6 . . ? C5 C4 H4B 108.6 . . ? C3 C4 H4B 108.6 . . ? H4A C4 H4B 107.6 . . ? C6 C5 C4 174.94(15) . . ? C5 C6 C7 179.11(16) . . ? C6 C7 C8 114.52(13) . . ? C6 C7 H7A 108.6 . . ? C8 C7 H7A 108.6 . . ? C6 C7 H7B 108.6 . . ? C8 C7 H7B 108.6 . . ? H7A C7 H7B 107.6 . . ? C9 C8 C7 115.77(14) . . ? C9 C8 H8A 108.3 . . ? C7 C8 H8A 108.3 . . ? C9 C8 H8B 108.3 . . ? C7 C8 H8B 108.3 . . ? H8A C8 H8B 107.4 . . ? N10 C9 C8 115.20(12) . . ? N10 C9 H9A 108.5 . . ? C8 C9 H9A 108.5 . . ? N10 C9 H9B 108.5 . . ? C8 C9 H9B 108.5 . . ? H9A C9 H9B 107.5 . . ? N10 C11 C12 115.53(13) . . ? N10 C11 H11A 108.4 . . ? C12 C11 H11A 108.4 . . ? N10 C11 H11B 108.4 . . ? C12 C11 H11B 108.4 . . ? H11A C11 H11B 107.5 . . ? C11 C12 C13 114.06(13) . . ? C11 C12 H12A 108.7 . . ? C13 C12 H12A 108.7 . . ? C11 C12 H12B 108.7 . . ? C13 C12 H12B 108.7 . . ? H12A C12 H12B 107.6 . . ? C14 C13 C12 114.31(14) . . ? C14 C13 H13A 108.7 . . ? C12 C13 H13A 108.7 . . ? C14 C13 H13B 108.7 . . ? C12 C13 H13B 108.7 . . ? H13A C13 H13B 107.6 . . ? C15 C14 C13 176.91(15) . . ? C14 C15 C16 178.06(16) . . ? C15 C16 C17 115.31(12) . . ? C15 C16 H16A 108.4 . . ? C17 C16 H16A 108.4 . . ? C15 C16 H16B 108.4 . . ? C17 C16 H16B 108.4 . . ? H16A C16 H16B 107.5 . . ? C18 C17 C16 113.83(13) . . ? C18 C17 H17A 108.8 . . ? C16 C17 H17A 108.8 . . ? C18 C17 H17B 108.8 . . ? C16 C17 H17B 108.8 . . ? H17A C17 H17B 107.7 . . ? N1 C18 C17 113.67(11) . . ? N1 C18 H18A 108.8 . . ? C17 C18 H18A 108.8 . . ? N1 C18 H18B 108.8 . . ? C17 C18 H18B 108.8 . . ? H18A C18 H18B 107.7 . . ? N1 C19 C20 111.22(11) . . ? N1 C19 H19A 109.4 . . ? C20 C19 H19A 109.4 . . ? N1 C19 H19B 109.4 . . ? C20 C19 H19B 109.4 . . ? H19A C19 H19B 108.0 . . ? C19 C20 C21 112.74(12) . . ? C19 C20 H20A 109.0 . . ? C21 C20 H20A 109.0 . . ? C19 C20 H20B 109.0 . . ? C21 C20 H20B 109.0 . . ? H20A C20 H20B 107.8 . . ? C22 C21 C20 113.80(12) . . ? C22 C21 H21A 108.8 . . ? C20 C21 H21A 108.8 . . ? C22 C21 H21B 108.8 . . ? C20 C21 H21B 108.8 . . ? H21A C21 H21B 107.7 . . ? C21 C22 C23 113.51(13) . . ? C21 C22 H22A 108.9 . . ? C23 C22 H22A 108.9 . . ? C21 C22 H22B 108.9 . . ? C23 C22 H22B 108.9 . . ? H22A C22 H22B 107.7 . . ? N10 C23 C22 114.79(12) . . ? N10 C23 H23A 108.6 . . ? C22 C23 H23A 108.6 . . ? N10 C23 H23B 108.6 . . ? C22 C23 H23B 108.6 . . ? H23A C23 H23B 107.5 . . ? C9B N1A C19B 122.8(3) . . ? C9B N1A C2B 121.7(3) . . ? C19B N1A C2B 80.8(3) . . ? C9B N1A C19A 118.2(3) . . ? C19B N1A C19A 28.6(2) . . ? C2B N1A C19A 105.1(3) . . ? C9B N1A C2A 78.4(3) . . ? C19B N1A C2A 109.2(2) . . ? C2B N1A C2A 43.57(19) . . ? C19A N1A C2A 137.7(3) . . ? C9B N1A C9A 26.6(2) . . ? C19B N1A C9A 104.9(3) . . ? C2B N1A C9A 143.9(3) . . ? C19A N1A C9A 93.0(2) . . ? C2A N1A C9A 103.2(2) . . ? C3A C2A N1A 109.7(2) . . ? C3A C2A H2C 109.7 . . ? N1A C2A H2C 109.7 . . ? C3A C2A H2D 109.7 . . ? N1A C2A H2D 109.7 . . ? H2C C2A H2D 108.2 . . ? C3A C2B N1A 120.8(3) . . ? C3A C2B C19B 168.0(3) . . ? N1A C2B C19B 48.21(18) . . ? C3A C2B H2E 107.1 . . ? N1A C2B H2E 107.1 . . ? C19B C2B H2E 82.9 . . ? C3A C2B H2F 107.1 . . ? N1A C2B H2F 107.1 . . ? C19B C2B H2F 75.4 . . ? H2E C2B H2F 106.8 . . ? C2B C3A C2A 46.8(2) . . ? C2B C3A C4A 116.8(2) . . ? C2A C3A C4A 116.99(18) . . ? C2B C3A H3C 63.9 . . ? C2A C3A H3C 108.0 . . ? C4A C3A H3C 108.0 . . ? C2B C3A H3D 134.9 . . ? C2A C3A H3D 108.0 . . ? C4A C3A H3D 108.0 . . ? H3C C3A H3D 107.3 . . ? C5A C4A C3A 115.41(15) . . ? C5A C4A H4C 108.4 . . ? C3A C4A H4C 108.4 . . ? C5A C4A H4D 108.4 . . ? C3A C4A H4D 108.4 . . ? H4C C4A H4D 107.5 . . ? C6A C5A C4A 175.65(16) . . ? C5A C6A C7A 169.1(2) . . ? C5A C6A C7B 166.8(3) . . ? C7A C6A C7B 23.7(2) . . ? C6A C7A C8A 113.7(4) . . ? C6A C7A H7C 108.8 . . ? C8A C7A H7C 108.8 . . ? C6A C7A H7D 108.8 . . ? C8A C7A H7D 108.8 . . ? H7C C7A H7D 107.7 . . ? C9A C8A C7A 114.4(4) 2_655 . ? C9A C8A H8C 108.7 2_655 . ? C7A C8A H8C 108.7 . . ? C9A C8A H8D 108.7 2_655 . ? C7A C8A H8D 108.7 . . ? H8C C8A H8D 107.6 . . ? C8A C9A N1A 113.3(3) 2_655 . ? C8A C9A H9C 108.9 2_655 . ? N1A C9A H9C 108.9 . . ? C8A C9A H9D 108.9 2_655 . ? N1A C9A H9D 108.9 . . ? H9C C9A H9D 107.7 . . ? C20A C19A N1A 123.0(3) . . ? C20A C19A H19C 106.6 . . ? N1A C19A H19C 106.6 . . ? C20A C19A H19D 106.6 . . ? N1A C19A H19D 106.6 . . ? H19C C19A H19D 106.5 . . ? C21A C20A C19A 112.3(4) . . ? C21A C20A H20C 109.1 . . ? C19A C20A H20C 109.1 . . ? C21A C20A H20D 109.1 . . ? C19A C20A H20D 109.1 . . ? H20C C20A H20D 107.9 . . ? C8B C7B C6A 113.4(4) . . ? C8B C7B H7E 108.9 . . ? C6A C7B H7E 108.9 . . ? C8B C7B H7F 108.9 . . ? C6A C7B H7F 108.9 . . ? H7E C7B H7F 107.7 . . ? C7B C8B C9B 119.1(5) . 2_655 ? C7B C8B H8E 107.5 . . ? C9B C8B H8E 107.5 2_655 . ? C7B C8B H8F 107.5 . . ? C9B C8B H8F 107.5 2_655 . ? H8E C8B H8F 107.0 . . ? N1A C9B C8B 119.6(4) . 2_655 ? N1A C9B H9E 107.4 . . ? C8B C9B H9E 107.4 2_655 . ? N1A C9B H9F 107.4 . . ? C8B C9B H9F 107.4 2_655 . ? H9E C9B H9F 106.9 . . ? N1A C19B C20B 107.1(3) . . ? N1A C19B C2B 51.03(18) . . ? C20B C19B C2B 125.2(3) . . ? N1A C19B H19E 110.3 . . ? C20B C19B H19E 110.3 . . ? C2B C19B H19E 124.2 . . ? N1A C19B H19F 110.3 . . ? C20B C19B H19F 110.3 . . ? C2B C19B H19F 59.3 . . ? H19E C19B H19F 108.5 . . ? C19B C20B C21A 118.2(3) . . ? C19B C20B H20E 107.8 . . ? C21A C20B H20E 107.8 . . ? C19B C20B H20F 107.8 . . ? C21A C20B H20F 107.8 . . ? H20E C20B H20F 107.1 . . ? C20A C21A C20A 114.3(5) . 2_655 ? C20A C21A C20B 118.1(3) . 2_655 ? C20A C21A C20B 22.3(2) 2_655 2_655 ? C20A C21A C20B 22.3(2) . . ? C20A C21A C20B 118.1(3) 2_655 . ? C20B C21A C20B 130.6(4) 2_655 . ? C20A C21A H21C 108.7 . . ? C20A C21A H21C 108.7 2_655 . ? C20B C21A H21C 87.2 2_655 . ? C20B C21A H21C 122.9 . . ? C20A C21A H21D 108.7 . . ? C20A C21A H21D 108.7 2_655 . ? C20B C21A H21D 122.9 2_655 . ? C20B C21A H21D 87.2 . . ? H21C C21A H21D 107.6 . . ? _diffrn_measured_fraction_theta_max 0.477 _diffrn_reflns_theta_full 27.97 _diffrn_measured_fraction_theta_full 0.477 _refine_diff_density_max 0.382 _refine_diff_density_min -0.361 _refine_diff_density_rms 0.047 data_th13 _audit_creation_method SHELXL-97 _chemical_name_systematic ; (38) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H36 N2' _chemical_formula_weight 328.53 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 Orthorhombic _symmetry_space_group_name_H-M Fdd2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/4, -y+1/4, z+1/4' '-x+1/4, y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/4, -y+3/4, z+3/4' '-x+1/4, y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' 'x+3/4, -y+1/4, z+3/4' '-x+3/4, y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' 'x+3/4, -y+3/4, z+1/4' '-x+3/4, y+3/4, z+1/4' _cell_length_a 16.5939(8) _cell_length_b 28.3186(13) _cell_length_c 8.6029(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4042.6(3) _cell_formula_units_Z 8 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description polyhedron _exptl_crystal_colour colorless _exptl_crystal_size_max .36 _exptl_crystal_size_mid .30 _exptl_crystal_size_min .18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.080 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1456 _exptl_absorpt_coefficient_mu 0.062 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38.' _exptl_absorpt_correction_T_min 0.74 _exptl_absorpt_correction_T_max 0.98 _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7363 _diffrn_reflns_av_R_equivalents 0.0243 _diffrn_reflns_av_sigmaI/netI 0.0214 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.76 _diffrn_reflns_theta_max 25.64 _reflns_number_total 1750 _reflns_number_gt 1484 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0619P)^2^+2.1198P] 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 ride _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0034(5) _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 0(4) _refine_ls_number_reflns 1750 _refine_ls_number_parameters 119 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0505 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.1144 _refine_ls_wR_factor_gt 0.1074 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.138 _refine_ls_shift/su_max 0.020 _refine_ls_shift/su_mean 0.006 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 0.11105(10) 0.44221(6) 0.08411(19) 0.0506(5) Uani 1 1 d . . . C1 C 0.04838(16) 0.41420(7) 0.0074(3) 0.0588(6) Uani 1 1 d . . . H1A H -0.0009 0.4151 0.0722 0.071 Uiso 1 1 calc R . . H1B H 0.0666 0.3810 0.0020 0.071 Uiso 1 1 calc R . . C2 C 0.02689(15) 0.43063(8) -0.1560(3) 0.0611(6) Uani 1 1 d . . . H2A H 0.0296 0.4655 -0.1598 0.073 Uiso 1 1 calc R . . H2B H 0.0673 0.4181 -0.2300 0.073 Uiso 1 1 calc R . . C3 C -0.05668(16) 0.41481(9) -0.2071(3) 0.0667(7) Uani 1 1 d . . . H3A H -0.0657 0.4246 -0.3162 0.080 Uiso 1 1 calc R . . H3B H -0.0596 0.3799 -0.2030 0.080 Uiso 1 1 calc R . . C4 C -0.12028(17) 0.43475(9) -0.1090(3) 0.0619(7) Uani 1 1 d . . . C5 C -0.16741(17) 0.45274(10) -0.0230(3) 0.0665(7) Uani 1 1 d . . . C6 C -0.22010(18) 0.47392(12) 0.0912(4) 0.0863(9) Uani 1 1 d . . . H6A H -0.1911 0.4751 0.1918 0.104 Uiso 1 1 calc R . . H6B H -0.2674 0.4530 0.1053 0.104 Uiso 1 1 calc R . . C7 C -0.24979(16) 0.52264(14) 0.0539(3) 0.0909(11) Uani 1 1 d . . . H7A H -0.2748 0.5361 0.1486 0.109 Uiso 1 1 calc R . . H7B H -0.2925 0.5200 -0.0259 0.109 Uiso 1 1 calc R . . C8 C -0.18594(15) 0.55740(9) -0.0050(3) 0.0699(7) Uani 1 1 d . . . H8A H -0.1731 0.5495 -0.1144 0.084 Uiso 1 1 calc R . . H8B H -0.2092 0.5896 -0.0037 0.084 Uiso 1 1 calc R . . C9 C 0.12309(14) 0.42635(8) 0.2435(2) 0.0558(6) Uani 1 1 d D . . H9A H 0.1735 0.4404 0.2840 0.067 Uiso 1 1 calc R . . H9B H 0.1299 0.3916 0.2436 0.067 Uiso 1 1 calc R . . C10 C 0.05470(16) 0.43906(11) 0.3515(4) 0.0803(8) Uani 1 1 d D . . H10A H 0.0055 0.4267 0.3007 0.096 Uiso 0.50 1 calc PR A 1 H10B H 0.0630 0.4194 0.4454 0.096 Uiso 0.50 1 calc PR A 1 H10C H 0.0718 0.4369 0.4615 0.096 Uiso 0.50 1 calc PR A 2 H10D H 0.0079 0.4180 0.3349 0.096 Uiso 0.50 1 calc PR A 2 C11A C 0.0338(2) 0.48317(16) 0.4064(5) 0.0471(10) Uani 0.50 1 d PD . 1 H11A H 0.0814 0.5043 0.4056 0.057 Uiso 0.50 1 calc PR . 1 H11B H 0.0137 0.4808 0.5144 0.057 Uiso 0.50 1 calc PR . 1 C11B C 0.0312(2) 0.49728(14) 0.3017(5) 0.0429(9) Uani 0.50 1 d PD . 2 H11C H 0.0802 0.5171 0.3105 0.052 Uiso 0.50 1 calc PR . 2 H11D H 0.0127 0.4984 0.1923 0.052 Uiso 0.50 1 calc PR . 2 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 0.0566(10) 0.0452(9) 0.0499(11) 0.0071(8) -0.0090(9) 0.0101(8) C1 0.0898(17) 0.0342(10) 0.0525(13) 0.0065(9) -0.0096(12) 0.0028(10) C2 0.0828(17) 0.0489(12) 0.0518(13) -0.0005(10) -0.0117(12) 0.0043(11) C3 0.0966(18) 0.0519(12) 0.0516(13) -0.0104(10) -0.0161(14) -0.0042(12) C4 0.0802(17) 0.0590(15) 0.0465(13) -0.0015(11) -0.0183(13) -0.0232(13) C5 0.0792(16) 0.0738(15) 0.0466(13) -0.0028(13) -0.0062(14) -0.0348(13) C6 0.091(2) 0.103(2) 0.0648(16) -0.0114(17) 0.0165(16) -0.0413(18) C7 0.0546(15) 0.156(3) 0.0618(16) -0.040(2) 0.0126(13) -0.0131(18) C8 0.0774(17) 0.0794(16) 0.0531(14) -0.0139(12) -0.0026(13) 0.0232(14) C9 0.0603(13) 0.0585(12) 0.0485(12) 0.0030(10) -0.0034(11) 0.0156(11) C10 0.0532(13) 0.112(2) 0.0761(17) -0.0353(17) 0.0047(13) 0.0013(15) C11A 0.050(2) 0.058(3) 0.033(2) 0.0074(19) -0.0055(19) -0.0015(18) C11B 0.042(2) 0.044(2) 0.043(2) 0.0018(19) 0.0037(16) 0.000(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C9 1.457(3) . ? N1 C8 1.460(3) 2_565 ? N1 C1 1.465(3) . ? C1 C2 1.523(3) . ? C2 C3 1.522(3) . ? C3 C4 1.465(4) . ? C4 C5 1.191(4) . ? C5 C6 1.446(4) . ? C6 C7 1.500(5) . ? C7 C8 1.532(4) . ? C8 N1 1.460(3) 2_565 ? C9 C10 1.510(3) . ? C10 C11A 1.379(5) . ? C10 C11B 1.748(5) . ? C11A C11B 1.511(5) 2_565 ? C11B C11A 1.511(5) 2_565 ? 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 C9 N1 C8 112.32(17) . 2_565 ? C9 N1 C1 110.76(17) . . ? C8 N1 C1 111.81(18) 2_565 . ? N1 C1 C2 114.61(19) . . ? C3 C2 C1 113.0(2) . . ? C4 C3 C2 112.10(19) . . ? C5 C4 C3 174.9(2) . . ? C4 C5 C6 175.4(3) . . ? C5 C6 C7 115.8(3) . . ? C6 C7 C8 115.8(2) . . ? N1 C8 C7 114.8(2) 2_565 . ? N1 C9 C10 113.7(2) . . ? C11A C10 C9 128.0(3) . . ? C11A C10 C11B 34.3(2) . . ? C9 C10 C11B 104.0(2) . . ? C10 C11A C11B 107.9(3) . 2_565 ? C11A C11B C10 111.0(3) 2_565 . ? _diffrn_measured_fraction_theta_max 0.947 _diffrn_reflns_theta_full 25.64 _diffrn_measured_fraction_theta_full 0.947 _refine_diff_density_max 0.180 _refine_diff_density_min -0.146 _refine_diff_density_rms 0.028 data_th10 _audit_creation_method SHELXL-97 _chemical_name_systematic ; (39) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H38 N2' _chemical_formula_weight 342.55 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 Fdd2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/4, -y+1/4, z+1/4' '-x+1/4, y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/4, -y+3/4, z+3/4' '-x+1/4, y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' 'x+3/4, -y+1/4, z+3/4' '-x+3/4, y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' 'x+3/4, -y+3/4, z+1/4' '-x+3/4, y+3/4, z+1/4' _cell_length_a 16.0954(4) _cell_length_b 33.2375(9) _cell_length_c 7.8746(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4212.68(19) _cell_formula_units_Z 8 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description polyhedron _exptl_crystal_colour colorless _exptl_crystal_size_max .32 _exptl_crystal_size_mid .30 _exptl_crystal_size_min .28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.080 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1520 _exptl_absorpt_coefficient_mu 0.062 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38.' _exptl_absorpt_correction_T_min 0.78 _exptl_absorpt_correction_T_max 0.93 _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7681 _diffrn_reflns_av_R_equivalents 0.0173 _diffrn_reflns_av_sigmaI/netI 0.0164 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -39 _diffrn_reflns_limit_k_max 40 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.45 _diffrn_reflns_theta_max 25.59 _reflns_number_total 1749 _reflns_number_gt 1659 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0344P)^2^+1.3014P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1(2) _refine_ls_number_reflns 1749 _refine_ls_number_parameters 190 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0269 _refine_ls_R_factor_gt 0.0245 _refine_ls_wR_factor_ref 0.0624 _refine_ls_wR_factor_gt 0.0609 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.042 _refine_ls_shift/su_mean 0.009 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 0.04578(6) 0.58538(3) 0.41650(12) 0.0313(2) Uani 1 1 d . . . C1 C 0.07768(9) 0.58589(4) 0.24152(18) 0.0405(3) Uani 1 1 d . . . H1A H 0.0460(9) 0.6065(4) 0.179(2) 0.047(4) Uiso 1 1 d . . . H1B H 0.1370(10) 0.5962(4) 0.245(2) 0.046(4) Uiso 1 1 d . . . C2 C 0.07554(9) 0.54670(5) 0.13931(19) 0.0481(4) Uani 1 1 d . . . H2A H 0.0876(11) 0.5224(5) 0.213(3) 0.065(5) Uiso 1 1 d . . . H2B H 0.1214(13) 0.5472(6) 0.065(3) 0.088(6) Uiso 1 1 d . . . C3 C -0.00269(9) 0.53862(5) 0.0388(2) 0.0432(3) Uani 1 1 d . . . H3A H -0.0500(11) 0.5368(4) 0.111(2) 0.053(5) Uiso 1 1 d . . . H3B H -0.0163(10) 0.5603(5) -0.029(2) 0.058(4) Uiso 1 1 d . . . C4 C 0.0000 0.5000 -0.0671(2) 0.0453(5) Uani 1 2 d S . . H4 H 0.0500(9) 0.5015(4) -0.140(2) 0.050(4) Uiso 1 1 d . . . C5 C 0.08946(7) 0.55694(4) 0.52830(18) 0.0336(3) Uani 1 1 d . . . H5A H 0.0741(8) 0.5297(4) 0.502(2) 0.037(4) Uiso 1 1 d . . . H5B H 0.0707(8) 0.5620(4) 0.644(2) 0.044(4) Uiso 1 1 d . . . C6 C 0.18315(7) 0.56066(4) 0.52702(18) 0.0345(3) Uani 1 1 d . . . H6A H 0.1998(7) 0.5885(4) 0.5438(18) 0.032(3) Uiso 1 1 d . . . H6B H 0.2065(8) 0.5535(4) 0.4159(19) 0.035(3) Uiso 1 1 d . . . C7 C -0.22381(8) 0.46606(4) 0.66281(18) 0.0392(3) Uani 1 1 d . . . H7A H -0.2035(9) 0.4569(4) 0.778(2) 0.045(4) Uiso 1 1 d . . . H7B H -0.2844(10) 0.4622(4) 0.662(2) 0.052(4) Uiso 1 1 d . . . C8 C -0.20768(7) 0.50908(4) 0.63695(17) 0.0342(3) Uani 1 1 d . . . C9 C -0.19503(7) 0.54397(4) 0.61330(16) 0.0331(3) Uani 1 1 d . . . C10 C -0.17780(8) 0.58693(4) 0.5871(2) 0.0365(3) Uani 1 1 d . . . H10A H -0.2045(9) 0.6023(4) 0.682(2) 0.039(4) Uiso 1 1 d . . . H10B H -0.2043(10) 0.5958(4) 0.478(2) 0.050(4) Uiso 1 1 d . . . C11 C -0.08504(8) 0.59657(4) 0.58109(17) 0.0329(3) Uani 1 1 d . . . H11A H -0.0777(8) 0.6261(4) 0.5793(17) 0.038(3) Uiso 1 1 d . . . H11B H -0.0590(9) 0.5863(4) 0.684(2) 0.040(4) Uiso 1 1 d . . . C12 C -0.04419(8) 0.57851(3) 0.42401(15) 0.0301(3) Uani 1 1 d . . . H12A H -0.0699(7) 0.5908(4) 0.3208(19) 0.030(3) Uiso 1 1 d . . . H12B H -0.0595(7) 0.5489(3) 0.4225(16) 0.024(3) 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 0.0343(5) 0.0296(5) 0.0301(6) 0.0051(4) 0.0030(5) -0.0003(4) C1 0.0403(7) 0.0477(8) 0.0335(7) 0.0104(6) 0.0047(6) -0.0050(6) C2 0.0378(8) 0.0714(10) 0.0352(8) -0.0082(7) 0.0035(7) 0.0096(7) C3 0.0451(8) 0.0517(8) 0.0326(7) 0.0063(6) -0.0050(7) 0.0100(6) C4 0.0481(12) 0.0628(12) 0.0250(10) 0.000 0.000 0.0075(10) C5 0.0352(6) 0.0314(6) 0.0343(7) 0.0068(5) 0.0043(6) 0.0012(5) C6 0.0341(6) 0.0309(7) 0.0385(7) -0.0038(5) 0.0055(6) -0.0037(5) C7 0.0319(7) 0.0425(7) 0.0431(8) 0.0054(6) 0.0053(6) -0.0013(5) C8 0.0242(6) 0.0443(7) 0.0341(7) -0.0028(6) 0.0043(5) 0.0039(5) C9 0.0235(6) 0.0432(7) 0.0326(7) -0.0067(5) 0.0030(5) 0.0056(5) C10 0.0331(7) 0.0350(7) 0.0415(8) -0.0075(6) -0.0012(6) 0.0092(5) C11 0.0360(7) 0.0302(6) 0.0324(7) -0.0038(5) -0.0020(6) 0.0022(5) C12 0.0337(6) 0.0263(5) 0.0304(7) 0.0013(5) 0.0000(5) 0.0010(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 C12 1.4671(16) . ? N1 C1 1.4705(17) . ? N1 C5 1.4706(16) . ? C1 C2 1.532(2) . ? C2 C3 1.511(2) . ? C3 C4 1.5312(19) . ? C4 C3 1.5314(19) 2_565 ? C5 C6 1.5132(17) . ? C6 C7 1.5365(19) 2_565 ? C7 C8 1.4676(17) . ? C7 C6 1.5364(19) 2_565 ? C8 C9 1.1920(17) . ? C9 C10 1.4691(18) . ? C10 C11 1.5277(17) . ? C11 C12 1.5239(17) . ? 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 C12 N1 C1 112.60(10) . . ? C12 N1 C5 110.36(9) . . ? C1 N1 C5 113.67(10) . . ? N1 C1 C2 118.33(12) . . ? C3 C2 C1 116.42(12) . . ? C2 C3 C4 114.23(11) . . ? C3 C4 C3 114.04(18) . 2_565 ? N1 C5 C6 114.83(10) . . ? C5 C6 C7 111.88(11) . 2_565 ? C8 C7 C6 113.04(11) . 2_565 ? C9 C8 C7 178.93(15) . . ? C8 C9 C10 178.63(14) . . ? C9 C10 C11 113.12(10) . . ? C12 C11 C10 111.35(11) . . ? N1 C12 C11 113.41(10) . . ? _diffrn_measured_fraction_theta_max 0.944 _diffrn_reflns_theta_full 25.59 _diffrn_measured_fraction_theta_full 0.944 _refine_diff_density_max 0.074 _refine_diff_density_min -0.115 _refine_diff_density_rms 0.024 data_th15 _audit_creation_method SHELXL-97 _chemical_name_systematic ; (42) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H44 N2' _chemical_formula_weight 384.63 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)/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 9.80340(10) _cell_length_b 11.9812(2) _cell_length_c 20.9007(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.5310(10) _cell_angle_gamma 90.00 _cell_volume 2454.05(6) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description polyhedron _exptl_crystal_colour colorless _exptl_crystal_size_max .35 _exptl_crystal_size_mid .34 _exptl_crystal_size_min .32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.041 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 0.060 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38.' _exptl_absorpt_correction_T_min 0.73 _exptl_absorpt_correction_T_max 0.97 _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17751 _diffrn_reflns_av_R_equivalents 0.0216 _diffrn_reflns_av_sigmaI/netI 0.0212 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 25.56 _reflns_number_total 4249 _reflns_number_gt 3407 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0570P)^2^+0.5015P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4249 _refine_ls_number_parameters 429 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0544 _refine_ls_R_factor_gt 0.0403 _refine_ls_wR_factor_ref 0.1104 _refine_ls_wR_factor_gt 0.1002 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _refine_ls_shift/su_max 0.082 _refine_ls_shift/su_mean 0.009 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 0.73469(11) 1.14688(9) 0.12875(5) 0.0364(3) Uani 1 1 d . . . C2 C 0.7456(2) 1.17161(14) 0.06011(7) 0.0562(5) Uani 1 1 d . . . H2A H 0.8435(19) 1.1956(14) 0.0528(8) 0.064(5) Uiso 1 1 d . . . H2B H 0.684(2) 1.2364(17) 0.0483(9) 0.079(6) Uiso 1 1 d . . . C3 C 0.7115(2) 1.07289(14) 0.01675(8) 0.0558(5) Uani 1 1 d . . . H3A H 0.615(2) 1.0392(18) 0.0242(10) 0.094(7) Uiso 1 1 d . . . H3B H 0.716(2) 1.0938(17) -0.0294(10) 0.091(6) Uiso 1 1 d . . . C4 C 0.81031(18) 0.97768(14) 0.02741(9) 0.0525(4) Uani 1 1 d . . . H4A H 0.808(2) 0.9543(17) 0.0765(10) 0.089(6) Uiso 1 1 d . . . H4B H 0.904(2) 1.0067(18) 0.0239(10) 0.100(7) Uiso 1 1 d . . . C5 C 0.78339(16) 0.88089(13) -0.01465(7) 0.0460(4) Uani 1 1 d . . . C6 C 0.75626(15) 0.79808(13) -0.04461(7) 0.0431(4) Uani 1 1 d . . . C7 C 0.72179(17) 0.69489(13) -0.07920(7) 0.0468(4) Uani 1 1 d . . . H7B H 0.6249(18) 0.6768(13) -0.0763(7) 0.053(4) Uiso 1 1 d . . . H7B H 0.7387(17) 0.7047(13) -0.1257(8) 0.061(5) Uiso 1 1 d . . . C8 C 0.79866(16) 0.59042(13) -0.05608(7) 0.0431(4) Uani 1 1 d . . . H8A H 0.7882(15) 0.5332(13) -0.0874(7) 0.049(4) Uiso 1 1 d . . . H8B H 0.8984(16) 0.6052(12) -0.0534(7) 0.045(4) Uiso 1 1 d . . . C9 C 0.75075(16) 0.54205(12) 0.00687(7) 0.0430(4) Uani 1 1 d . . . H9A H 0.6488(17) 0.5277(12) 0.0030(7) 0.049(4) Uiso 1 1 d . . . H9B H 0.7946(16) 0.4683(14) 0.0154(7) 0.054(4) Uiso 1 1 d . . . N10 N 0.77339(11) 0.61655(9) 0.06176(5) 0.0340(3) Uani 1 1 d . . . C11 C 0.68403(15) 0.59108(12) 0.11472(7) 0.0404(3) Uani 1 1 d . . . H11A H 0.7156(14) 0.6335(11) 0.1524(7) 0.038(4) Uiso 1 1 d . . . H11B H 0.6887(15) 0.5094(14) 0.1275(7) 0.053(4) Uiso 1 1 d . . . C12 C 0.53564(15) 0.62219(13) 0.10193(7) 0.0447(4) Uani 1 1 d . . . H12A H 0.4956(16) 0.5748(13) 0.0673(8) 0.055(4) Uiso 1 1 d . . . H12B H 0.4851(16) 0.6048(13) 0.1404(8) 0.053(4) Uiso 1 1 d . . . C13 C 0.51360(15) 0.74397(13) 0.08279(7) 0.0427(4) Uani 1 1 d . . . H13A H 0.5642(16) 0.7592(12) 0.0441(7) 0.048(4) Uiso 1 1 d . . . H13B H 0.4159(17) 0.7554(13) 0.0714(7) 0.052(4) Uiso 1 1 d . . . C14 C 0.55578(13) 0.82423(12) 0.13268(7) 0.0406(3) Uani 1 1 d . . . C15 C 0.58971(14) 0.89028(12) 0.17282(7) 0.0416(3) Uani 1 1 d . . . C16 C 0.63366(17) 0.97353(13) 0.22039(8) 0.0469(4) Uani 1 1 d . . . H16A H 0.7336(17) 0.9817(12) 0.2182(7) 0.050(4) Uiso 1 1 d . . . H16B H 0.6136(16) 0.9464(14) 0.2646(8) 0.063(5) Uiso 1 1 d . . . C17 C 0.56792(17) 1.08835(13) 0.21114(8) 0.0494(4) Uani 1 1 d . . . H17A H 0.4674(18) 1.0821(14) 0.2166(8) 0.063(5) Uiso 1 1 d . . . H17B H 0.6049(16) 1.1382(13) 0.2461(8) 0.056(4) Uiso 1 1 d . . . C18 C 0.59123(15) 1.14143(13) 0.14650(8) 0.0452(4) Uani 1 1 d . . . H18A H 0.5495(16) 1.2191(15) 0.1458(7) 0.060(5) Uiso 1 1 d . . . H18B H 0.5419(15) 1.0974(12) 0.1143(7) 0.045(4) Uiso 1 1 d . . . C19 C 0.81054(15) 1.23029(12) 0.16709(7) 0.0419(4) Uani 1 1 d . . . H19A H 0.7932(15) 1.3065(13) 0.1492(7) 0.050(4) Uiso 1 1 d . . . H19B H 0.7720(15) 1.2292(12) 0.2114(7) 0.045(4) Uiso 1 1 d . . . C20 C 0.96316(16) 1.20630(12) 0.17233(8) 0.0448(4) Uani 1 1 d . . . H20A H 1.0031(16) 1.2069(13) 0.1287(8) 0.054(4) Uiso 1 1 d . . . H20B H 1.0082(16) 1.2666(14) 0.1970(8) 0.060(5) Uiso 1 1 d . . . C21 C 0.99554(14) 1.09540(12) 0.20475(7) 0.0380(3) Uani 1 1 d . . . H21A H 0.9473(15) 1.0893(12) 0.2462(8) 0.051(4) Uiso 1 1 d . . . H21B H 0.9572(14) 1.0360(12) 0.1780(7) 0.039(4) Uiso 1 1 d . . . C22 C 1.14685(14) 1.07328(12) 0.21673(8) 0.0419(3) Uani 1 1 d . . . H22A H 1.1890(16) 1.1372(13) 0.2396(7) 0.052(4) Uiso 1 1 d . . . H22B H 1.1918(15) 1.0709(12) 0.1761(7) 0.047(4) Uiso 1 1 d . . . C23 C 1.17717(15) 0.96711(12) 0.25513(7) 0.0408(3) Uani 1 1 d . . . H23A H 1.1396(14) 0.9764(12) 0.2992(7) 0.045(4) Uiso 1 1 d . . . H23B H 1.2747(17) 0.9561(12) 0.2603(7) 0.050(4) Uiso 1 1 d . . . C24 C 1.11633(14) 0.86019(12) 0.22660(6) 0.0357(3) Uani 1 1 d . . . H24A H 1.0151(15) 0.8667(11) 0.2250(6) 0.034(3) Uiso 1 1 d . . . H24B H 1.1355(14) 0.7973(12) 0.2565(7) 0.045(4) Uiso 1 1 d . . . C25 C 1.16915(15) 0.83147(14) 0.16083(7) 0.0433(4) Uani 1 1 d . . . H25A H 1.1458(15) 0.8920(13) 0.1303(7) 0.047(4) Uiso 1 1 d . . . H25B H 1.2677(18) 0.8294(13) 0.1637(8) 0.060(5) Uiso 1 1 d . . . C26 C 1.11524(14) 0.72168(13) 0.13318(8) 0.0425(4) Uani 1 1 d . . . H26A H 1.1668(17) 0.7022(13) 0.0945(8) 0.057(4) Uiso 1 1 d . . . H26B H 1.1301(16) 0.6590(14) 0.1652(8) 0.058(5) Uiso 1 1 d . . . C27 C 0.96411(14) 0.72417(12) 0.11405(7) 0.0367(3) Uani 1 1 d . . . H27A H 0.9058(15) 0.7430(12) 0.1523(7) 0.043(4) Uiso 1 1 d . . . H27B H 0.9482(14) 0.7828(13) 0.0839(7) 0.044(4) Uiso 1 1 d . . . C28 C 0.91734(14) 0.61563(12) 0.08306(7) 0.0390(3) Uani 1 1 d . . . H28A H 0.9759(15) 0.6015(12) 0.0456(7) 0.044(4) Uiso 1 1 d . . . H28B H 0.9350(15) 0.5527(13) 0.1137(7) 0.048(4) 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 0.0439(7) 0.0292(6) 0.0358(6) -0.0018(5) -0.0051(5) 0.0040(5) C2 0.0903(14) 0.0383(9) 0.0397(9) 0.0031(7) -0.0020(8) 0.0062(9) C3 0.0881(14) 0.0421(9) 0.0366(8) 0.0001(7) -0.0088(8) 0.0137(9) C4 0.0531(10) 0.0456(9) 0.0586(10) -0.0100(8) -0.0009(8) 0.0053(8) C5 0.0530(9) 0.0437(9) 0.0418(8) 0.0022(7) 0.0089(7) 0.0101(7) C6 0.0503(9) 0.0445(9) 0.0348(7) 0.0012(7) 0.0056(6) 0.0118(7) C7 0.0515(10) 0.0520(10) 0.0365(8) -0.0066(7) -0.0066(7) 0.0101(8) C8 0.0470(9) 0.0432(9) 0.0387(8) -0.0165(7) -0.0074(6) 0.0092(7) C9 0.0493(9) 0.0332(8) 0.0457(8) -0.0111(6) -0.0109(7) 0.0024(7) N10 0.0361(6) 0.0307(6) 0.0348(6) -0.0052(4) -0.0074(5) 0.0009(5) C11 0.0499(8) 0.0320(8) 0.0389(8) 0.0029(6) -0.0067(6) -0.0053(6) C12 0.0435(8) 0.0500(9) 0.0407(8) -0.0034(7) 0.0000(7) -0.0162(7) C13 0.0317(7) 0.0570(10) 0.0392(8) -0.0005(7) 0.0004(6) 0.0037(7) C14 0.0301(7) 0.0459(9) 0.0458(8) 0.0051(7) 0.0054(6) 0.0030(6) C15 0.0341(7) 0.0440(8) 0.0466(8) 0.0049(7) 0.0037(6) -0.0005(6) C16 0.0478(9) 0.0474(9) 0.0456(9) 0.0045(7) -0.0002(7) -0.0069(7) C17 0.0449(9) 0.0481(9) 0.0554(10) -0.0102(7) 0.0069(7) -0.0003(7) C18 0.0410(8) 0.0373(8) 0.0564(9) -0.0058(7) -0.0123(7) 0.0106(7) C19 0.0500(9) 0.0278(8) 0.0475(9) -0.0051(6) -0.0044(7) 0.0042(6) C20 0.0460(8) 0.0322(8) 0.0562(10) -0.0048(7) -0.0013(7) -0.0040(7) C21 0.0358(8) 0.0376(8) 0.0403(8) -0.0021(6) -0.0027(6) -0.0028(6) C22 0.0344(7) 0.0404(8) 0.0507(9) -0.0085(7) -0.0048(7) -0.0071(6) C23 0.0339(8) 0.0469(9) 0.0412(8) -0.0085(6) -0.0083(6) 0.0032(7) C24 0.0317(7) 0.0385(8) 0.0368(7) -0.0016(6) -0.0023(6) 0.0019(6) C25 0.0304(8) 0.0548(10) 0.0449(8) -0.0121(7) 0.0033(6) -0.0056(7) C26 0.0327(7) 0.0485(9) 0.0462(8) -0.0138(7) -0.0016(6) 0.0033(6) C27 0.0359(7) 0.0343(8) 0.0395(8) -0.0035(6) -0.0065(6) 0.0040(6) C28 0.0376(8) 0.0359(8) 0.0430(8) -0.0068(6) -0.0092(6) 0.0088(6) _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 C18 1.4655(19) . ? N1 C19 1.4704(17) . ? N1 C2 1.4715(19) . ? C2 C3 1.522(2) . ? C3 C4 1.509(2) . ? C4 C5 1.475(2) . ? C5 C6 1.199(2) . ? C6 C7 1.467(2) . ? C7 C8 1.533(2) . ? C8 C9 1.523(2) . ? C9 N10 1.4659(16) . ? N10 C11 1.4620(18) . ? N10 C28 1.4684(17) . ? C11 C12 1.519(2) . ? C12 C13 1.527(2) . ? C13 C14 1.470(2) . ? C14 C15 1.1940(19) . ? C15 C16 1.465(2) . ? C16 C17 1.529(2) . ? C17 C18 1.516(2) . ? C19 C20 1.525(2) . ? C20 C21 1.521(2) . ? C21 C22 1.5210(19) . ? C22 C23 1.529(2) . ? C23 C24 1.5275(19) . ? C24 C25 1.5213(19) . ? C25 C26 1.526(2) . ? C26 C27 1.5245(19) . ? C27 C28 1.5182(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 C18 N1 C19 111.54(11) . . ? C18 N1 C2 110.56(13) . . ? C19 N1 C2 110.21(12) . . ? N1 C2 C3 113.79(13) . . ? C4 C3 C2 111.70(15) . . ? C5 C4 C3 113.74(14) . . ? C6 C5 C4 174.51(16) . . ? C5 C6 C7 178.03(15) . . ? C6 C7 C8 115.34(12) . . ? C9 C8 C7 115.01(13) . . ? N10 C9 C8 113.61(12) . . ? C11 N10 C9 112.59(11) . . ? C11 N10 C28 111.06(11) . . ? C9 N10 C28 110.91(11) . . ? N10 C11 C12 113.96(11) . . ? C11 C12 C13 114.14(12) . . ? C14 C13 C12 113.84(12) . . ? C15 C14 C13 179.35(16) . . ? C14 C15 C16 178.05(15) . . ? C15 C16 C17 114.29(13) . . ? C18 C17 C16 114.64(13) . . ? N1 C18 C17 114.38(12) . . ? N1 C19 C20 113.08(12) . . ? C21 C20 C19 112.92(12) . . ? C22 C21 C20 114.61(12) . . ? C21 C22 C23 113.98(12) . . ? C24 C23 C22 115.12(11) . . ? C25 C24 C23 113.81(12) . . ? C24 C25 C26 114.49(13) . . ? C27 C26 C25 114.00(12) . . ? C28 C27 C26 112.05(11) . . ? N10 C28 C27 113.56(11) . . ? _diffrn_measured_fraction_theta_max 0.923 _diffrn_reflns_theta_full 25.56 _diffrn_measured_fraction_theta_full 0.923 _refine_diff_density_max 0.268 _refine_diff_density_min -0.163 _refine_diff_density_rms 0.036 data_744hbo _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,10-Diaza-21-oxabicyclo[8.8.5]tricosa-5,14-diyne (43) ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H40 N2 O5' _chemical_formula_weight 388.54 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' 'O' 'O' 0.0106 0.0060 '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 8.899(3) _cell_length_b 12.364(4) _cell_length_c 20.155(6) _cell_angle_alpha 104.35(3) _cell_angle_beta 94.56(3) _cell_angle_gamma 99.02(3) _cell_volume 2105.5(12) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.05 _cell_measurement_theta_max 17.07 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.226 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9661 _exptl_absorpt_correction_T_max 0.9744 _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type NONIUS_CAD4 _diffrn_measurement_method \w2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 4 _diffrn_reflns_number 10779 _diffrn_reflns_av_R_equivalents 0.0355 _diffrn_reflns_av_sigmaI/netI 0.0487 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 27.98 _reflns_number_total 10134 _reflns_number_gt 6036 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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 w=1/[\s^2^(Fo^2^)+(0.1142P)^2^+0.1755P] 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 ride _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10134 _refine_ls_number_parameters 541 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1190 _refine_ls_R_factor_gt 0.0553 _refine_ls_wR_factor_ref 0.1878 _refine_ls_wR_factor_gt 0.1590 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.109 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.09502(16) 0.22851(12) 0.32761(7) 0.0288(3) Uani 1 d . . . N1A N 0.14614(19) 0.13332(13) 0.87310(9) 0.0402(4) Uani 1 d . . . N10 N 0.06922(18) 0.32425(12) 0.59220(8) 0.0342(3) Uani 1 d . . . N10A N 0.2313(2) 0.54645(14) 0.84202(10) 0.0459(4) Uani 1 d . . . O21 O 0.17445(14) 0.39792(10) 0.46597(6) 0.0346(3) Uani 1 d . . . O21A O 0.0165(2) 0.32876(17) 0.83727(12) 0.0385(4) Uani 0.75 d P A 3 O21B O 0.0337(10) 0.3091(7) 0.8084(4) 0.053(2) Uiso 0.25 d P A 4 C2 C 0.1155(2) 0.13546(15) 0.35902(9) 0.0306(4) Uani 1 d . . . H2A H 0.0240 0.0757 0.3444 0.037 Uiso 1 calc R . . H2B H 0.1243 0.1642 0.4093 0.037 Uiso 1 calc R . . C2A C 0.2122(3) 0.22331(18) 0.93557(11) 0.0456(5) Uani 1 d . . . H2C H 0.2019 0.2967 0.9272 0.055 Uiso 1 calc R . . H2D H 0.3220 0.2226 0.9439 0.055 Uiso 1 calc R . . C3 C 0.2554(2) 0.08400(16) 0.34021(10) 0.0348(4) Uani 1 d . . . H3A H 0.3478 0.1424 0.3569 0.042 Uiso 1 calc R . . H3B H 0.2493 0.0577 0.2899 0.042 Uiso 1 calc R . . C3A C 0.1411(4) 0.2142(2) 0.99972(14) 0.0713(8) Uani 1 d . . . H3C H 0.1368 0.1370 1.0048 0.086 Uiso 1 calc R . . H3D H 0.0358 0.2280 0.9950 0.086 Uiso 1 calc R . . C4 C 0.2681(2) -0.01568(16) 0.37133(10) 0.0393(4) Uani 1 d . . . H4A H 0.1790 -0.0761 0.3520 0.047 Uiso 1 calc R . . H4B H 0.3600 -0.0459 0.3580 0.047 Uiso 1 calc R . . C4A C 0.2315(4) 0.2991(2) 1.06433(13) 0.0742(9) Uani 1 d . . . H4C H 0.1786 0.2927 1.1044 0.089 Uiso 1 calc R . . H4D H 0.3331 0.2798 1.0718 0.089 Uiso 1 calc R . . C5 C 0.2764(2) 0.01542(15) 0.44657(10) 0.0355(4) Uani 1 d . . . C5A C 0.2497(3) 0.4167(2) 1.05933(11) 0.0526(6) Uani 1 d . . . C6 C 0.2796(2) 0.04004(15) 0.50758(10) 0.0354(4) Uani 1 d . . . C6A C 0.2652(3) 0.5094(2) 1.05318(12) 0.0568(6) Uani 1 d . . . C7 C 0.2783(2) 0.07246(16) 0.58261(10) 0.0385(4) Uani 1 d . . . H7A H 0.3793 0.1158 0.6048 0.046 Uiso 1 calc R . . H7B H 0.2591 0.0037 0.5988 0.046 Uiso 1 calc R . . C7A C 0.2801(4) 0.6218(2) 1.04021(15) 0.0827(10) Uani 1 d . . . H7C H 0.3888 0.6568 1.0473 0.099 Uiso 1 calc R B 1 H7D H 0.2278 0.6700 1.0735 0.099 Uiso 1 calc R B 1 C8 C 0.1553(2) 0.14430(16) 0.60413(10) 0.0384(4) Uani 1 d . . . H8A H 0.0541 0.1018 0.5818 0.046 Uiso 1 calc R . . H8B H 0.1545 0.1608 0.6542 0.046 Uiso 1 calc R . . C9 C 0.1888(2) 0.25481(15) 0.58319(9) 0.0333(4) Uani 1 d . . . H9A H 0.2844 0.3002 0.6102 0.040 Uiso 1 calc R . . H9B H 0.2058 0.2369 0.5345 0.040 Uiso 1 calc R . . C8A C 0.2097(9) 0.6160(5) 0.9644(3) 0.0544(13) Uani 0.50 d P C 1 H8C H 0.0994 0.5861 0.9585 0.065 Uiso 0.50 calc PR C 1 H8D H 0.2234 0.6929 0.9581 0.065 Uiso 0.50 calc PR C 1 C9A C 0.2868(5) 0.5384(4) 0.9073(2) 0.0337(8) Uani 0.50 d P C 1 H9C H 0.3984 0.5630 0.9155 0.040 Uiso 0.50 calc PR C 1 H9D H 0.2631 0.4594 0.9095 0.040 Uiso 0.50 calc PR C 1 C8B C 0.3042(8) 0.6245(5) 0.9750(3) 0.0585(15) Uani 0.50 d P C 2 H8E H 0.4067 0.6075 0.9681 0.070 Uiso 0.50 calc PR C 2 H8F H 0.3059 0.7025 0.9718 0.070 Uiso 0.50 calc PR C 2 C9B C 0.1987(9) 0.5505(5) 0.9188(3) 0.0670(15) Uani 0.50 d P C 2 H9E H 0.0976 0.5713 0.9240 0.080 Uiso 0.50 calc PR C 2 H9F H 0.1912 0.4732 0.9241 0.080 Uiso 0.50 calc PR C 2 C11 C -0.0726(2) 0.27066(15) 0.54550(9) 0.0346(4) Uani 1 d . . . H11A H -0.0901 0.1886 0.5406 0.041 Uiso 1 calc R . . H11B H -0.0604 0.2827 0.4998 0.041 Uiso 1 calc R . . C12 C -0.2117(2) 0.31717(18) 0.57096(10) 0.0406(4) Uani 1 d . . . H12A H -0.2003 0.3969 0.5701 0.049 Uiso 1 calc R . . H12B H -0.2163 0.3142 0.6189 0.049 Uiso 1 calc R . . C11A C 0.3080(4) 0.4760(3) 0.7854(2) 0.0287(7) Uani 0.50 d P C 1 H11C H 0.2604 0.4782 0.7404 0.034 Uiso 0.50 calc PR C 1 H11D H 0.2890 0.3968 0.7876 0.034 Uiso 0.50 calc PR C 1 C12A C 0.4827(6) 0.5173(5) 0.7910(3) 0.0394(13) Uani 0.50 d P C 1 H12C H 0.5022 0.5914 0.7808 0.047 Uiso 0.50 calc PR C 1 H12D H 0.5292 0.5267 0.8383 0.047 Uiso 0.50 calc PR C 1 C11B C 0.3495(6) 0.4806(4) 0.8304(3) 0.0592(12) Uani 0.50 d P C 2 H11E H 0.3067 0.4006 0.8252 0.071 Uiso 0.50 calc PR C 2 H11F H 0.4290 0.5058 0.8703 0.071 Uiso 0.50 calc PR C 2 C12B C 0.4178(12) 0.4929(6) 0.7679(4) 0.071(2) Uani 0.50 d P C 2 H12E H 0.4500 0.5745 0.7737 0.086 Uiso 0.50 calc PR C 2 H12F H 0.3345 0.4665 0.7297 0.086 Uiso 0.50 calc PR C 2 C13 C -0.3622(2) 0.25096(18) 0.52727(11) 0.0406(4) Uani 1 d . . . H13A H -0.3822 0.1749 0.5347 0.049 Uiso 1 calc R . . H13B H -0.4463 0.2893 0.5431 0.049 Uiso 1 calc R . . C13A C 0.5532(3) 0.4367(2) 0.74303(15) 0.0617(7) Uani 1 d . . . H13C H 0.6634 0.4670 0.7485 0.074 Uiso 1 calc R D 1 H13D H 0.5119 0.4342 0.6960 0.074 Uiso 1 calc R D 1 C14 C -0.3616(2) 0.24001(15) 0.45281(10) 0.0344(4) Uani 1 d . . . C14A C 0.5342(2) 0.31936(19) 0.74906(12) 0.0464(5) Uani 1 d . . . C15 C -0.3561(2) 0.23220(15) 0.39330(10) 0.0342(4) Uani 1 d . . . C15A C 0.5150(2) 0.22602(18) 0.75575(11) 0.0426(5) Uani 1 d . . . C16 C -0.3394(2) 0.22104(17) 0.32015(10) 0.0381(4) Uani 1 d . . . H16A H -0.3391 0.2948 0.3102 0.046 Uiso 1 calc R . . H16B H -0.4271 0.1672 0.2915 0.046 Uiso 1 calc R . . C16A C 0.4855(2) 0.11121(17) 0.76636(11) 0.0435(5) Uani 1 d . . . H16C H 0.5838 0.0875 0.7747 0.052 Uiso 1 calc R . . H16D H 0.4288 0.0581 0.7241 0.052 Uiso 1 calc R . . C17 C -0.1912(2) 0.17973(16) 0.30161(10) 0.0365(4) Uani 1 d . . . H17A H -0.1896 0.1074 0.3131 0.044 Uiso 1 calc R . . H17B H -0.1876 0.1668 0.2518 0.044 Uiso 1 calc R . . C17A C 0.3947(2) 0.10434(18) 0.82651(11) 0.0427(5) Uani 1 d . . . H17C H 0.3818 0.0269 0.8319 0.051 Uiso 1 calc R . . H17D H 0.4524 0.1557 0.8691 0.051 Uiso 1 calc R . . C18 C -0.0524(2) 0.26573(15) 0.34023(9) 0.0313(4) Uani 1 d . . . H18A H -0.0528 0.3366 0.3268 0.038 Uiso 1 calc R . . H18B H -0.0606 0.2818 0.3898 0.038 Uiso 1 calc R . . C18A C 0.2387(2) 0.13577(17) 0.81576(10) 0.0400(4) Uani 1 d . . . H18C H 0.2527 0.2123 0.8089 0.048 Uiso 1 calc R . . H18D H 0.1815 0.0833 0.7735 0.048 Uiso 1 calc R . . C19 C 0.2247(2) 0.32498(16) 0.34805(10) 0.0367(4) Uani 1 d . . . H19A H 0.1925 0.3884 0.3331 0.044 Uiso 1 calc R . . H19B H 0.3085 0.3032 0.3219 0.044 Uiso 1 calc R . . C19A C -0.0157(2) 0.13543(19) 0.85086(14) 0.0550(6) Uani 1 d . . . H19C H -0.0661 0.1562 0.8925 0.066 Uiso 1 calc R E 3 H19D H -0.0648 0.0578 0.8258 0.066 Uiso 1 calc R E 3 C20 C 0.2892(2) 0.36868(17) 0.42310(11) 0.0396(4) Uani 1 d . . . H20A H 0.3365 0.3103 0.4374 0.048 Uiso 1 calc R . . H20B H 0.3692 0.4357 0.4291 0.048 Uiso 1 calc R . . C20A C -0.0491(3) 0.2124(2) 0.80651(18) 0.0447(7) Uani 0.75 d P A 3 H20C H -0.0095 0.1875 0.7623 0.054 Uiso 0.75 calc PR A 3 H20D H -0.1604 0.2053 0.7970 0.054 Uiso 0.75 calc PR A 3 C20B C -0.0598(15) 0.2417(12) 0.8412(7) 0.068(3) Uiso 0.25 d P A 4 H20E H -0.1623 0.2215 0.8150 0.082 Uiso 0.25 calc PR A 4 H20F H -0.0690 0.2893 0.8869 0.082 Uiso 0.25 calc PR A 4 C22 C 0.2397(2) 0.45282(15) 0.53523(10) 0.0393(4) Uani 1 d . . . H22A H 0.2738 0.5339 0.5396 0.047 Uiso 1 calc R . . H22B H 0.3298 0.4210 0.5462 0.047 Uiso 1 calc R . . C22A C -0.0093(3) 0.3961(2) 0.79159(15) 0.0702(8) Uani 1 d . . . H22C H -0.1194 0.3967 0.7852 0.084 Uiso 1 calc R F 3 H22D H 0.0191 0.3591 0.7466 0.084 Uiso 1 calc R F 3 C23 C 0.1272(2) 0.43913(15) 0.58635(10) 0.0397(4) Uani 1 d . . . H23A H 0.1761 0.4851 0.6321 0.048 Uiso 1 calc R . . H23B H 0.0386 0.4719 0.5746 0.048 Uiso 1 calc R . . C23A C 0.0720(3) 0.5130(2) 0.81220(17) 0.0733(8) Uani 1 d . . . H23C H 0.0636 0.5418 0.7712 0.088 Uiso 1 calc R . . H23D H 0.0134 0.5555 0.8453 0.088 Uiso 1 calc R . . O1 O 0.1471(2) -0.07908(13) 0.90007(9) 0.0519(4) Uani 1 d . . . H1A H 0.150(3) -0.006(2) 0.8940(13) 0.062 Uiso 1 d . . . H1B H 0.188(3) -0.061(2) 0.9405(15) 0.062 Uiso 1 d . . . O2 O 0.1155(2) 0.18828(16) 0.18603(8) 0.0586(5) Uani 1 d . . . H2E H 0.105(3) 0.192(2) 0.2249(16) 0.070 Uiso 1 d . . . H2F H -0.021(3) 0.133(2) 0.1381(14) 0.070 Uiso 1 d . . . O3 O 0.3535(2) 0.77534(16) 0.85009(11) 0.0650(5) Uani 1 d . . . H3E H 0.299(3) 0.701(3) 0.8375(15) 0.078 Uiso 1 d . . . H3F H 0.280(4) 0.812(3) 0.8596(16) 0.078 Uiso 1 d . . . O4 O 0.3688(2) 0.09316(18) 0.15894(11) 0.0658(5) Uani 1 d . . . H4E H 0.351(4) 0.059(3) 0.1174(17) 0.079 Uiso 1 d . . . H4F H 0.446(4) 0.139(3) 0.1566(16) 0.079 Uiso 1 d . . . O5 O 0.3593(8) -0.0538(8) 0.0200(4) 0.085(2) Uani 0.50 d P . . O5A O 0.2910(8) -0.0512(8) 0.0316(4) 0.093(2) Uani 0.50 d P . . O6 O 0.5065(8) -0.1494(5) -0.0125(3) 0.0544(15) Uiso 0.25 d P . . 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 0.0225(7) 0.0329(7) 0.0330(7) 0.0124(6) 0.0049(6) 0.0044(6) N1A 0.0348(9) 0.0338(8) 0.0507(10) 0.0091(7) 0.0126(7) 0.0019(7) N10 0.0371(9) 0.0319(7) 0.0327(8) 0.0047(6) 0.0006(6) 0.0118(6) N10A 0.0429(10) 0.0388(9) 0.0576(11) 0.0134(8) 0.0010(8) 0.0138(7) O21 0.0288(6) 0.0343(6) 0.0375(7) 0.0065(5) -0.0014(5) 0.0034(5) O21A 0.0337(11) 0.0423(11) 0.0373(11) 0.0074(9) 0.0015(9) 0.0071(8) C2 0.0249(8) 0.0345(9) 0.0350(9) 0.0119(7) 0.0074(7) 0.0068(7) C2A 0.0532(13) 0.0412(11) 0.0427(11) 0.0113(9) 0.0148(9) 0.0046(9) C3 0.0282(9) 0.0425(10) 0.0351(9) 0.0092(8) 0.0070(7) 0.0113(8) C3A 0.109(2) 0.0453(13) 0.0652(16) 0.0164(11) 0.0468(16) 0.0089(14) C4 0.0404(11) 0.0380(10) 0.0421(10) 0.0073(8) 0.0096(8) 0.0176(8) C4A 0.133(3) 0.0578(15) 0.0431(13) 0.0210(11) 0.0359(15) 0.0268(16) C5 0.0347(10) 0.0326(9) 0.0445(11) 0.0143(8) 0.0080(8) 0.0139(7) C5A 0.0696(16) 0.0540(13) 0.0355(11) 0.0089(9) 0.0156(10) 0.0152(11) C6 0.0350(10) 0.0319(9) 0.0445(11) 0.0158(8) 0.0053(8) 0.0120(7) C6A 0.0724(17) 0.0512(13) 0.0407(12) 0.0046(10) 0.0041(11) 0.0065(12) C7 0.0439(11) 0.0372(10) 0.0408(10) 0.0192(8) 0.0040(8) 0.0124(8) C7A 0.127(3) 0.0435(14) 0.0646(18) 0.0035(12) -0.0012(18) 0.0013(15) C8 0.0434(11) 0.0414(10) 0.0368(10) 0.0174(8) 0.0093(8) 0.0130(8) C9 0.0358(10) 0.0326(9) 0.0324(9) 0.0093(7) 0.0009(7) 0.0094(7) C8A 0.081(4) 0.035(3) 0.047(3) 0.007(2) 0.010(3) 0.016(3) C9A 0.029(2) 0.037(2) 0.037(2) 0.0110(16) 0.0088(17) 0.0086(17) C8B 0.074(4) 0.039(3) 0.060(3) 0.012(2) 0.018(3) 0.000(3) C9B 0.089(5) 0.042(3) 0.069(4) 0.018(3) 0.002(4) 0.010(3) C11 0.0331(10) 0.0349(9) 0.0346(9) 0.0057(7) 0.0025(7) 0.0092(7) C12 0.0414(11) 0.0479(11) 0.0358(10) 0.0096(8) 0.0073(8) 0.0192(9) C11A 0.0285(19) 0.044(2) 0.0167(16) 0.0133(14) 0.0003(15) 0.0073(15) C12A 0.032(3) 0.038(2) 0.048(4) 0.013(2) 0.004(2) 0.0016(19) C11B 0.061(3) 0.049(3) 0.072(4) 0.020(2) 0.012(3) 0.012(2) C12B 0.126(9) 0.056(4) 0.050(4) 0.028(3) 0.025(4) 0.041(5) C13 0.0328(10) 0.0475(11) 0.0498(11) 0.0195(9) 0.0141(9) 0.0164(8) C13A 0.0475(14) 0.0496(13) 0.0918(19) 0.0239(13) 0.0161(13) 0.0077(11) C14 0.0218(8) 0.0330(9) 0.0488(11) 0.0110(8) 0.0032(7) 0.0065(7) C14A 0.0383(11) 0.0483(12) 0.0529(13) 0.0107(10) 0.0119(9) 0.0096(9) C15 0.0218(8) 0.0333(9) 0.0456(11) 0.0076(8) 0.0015(7) 0.0050(7) C15A 0.0366(11) 0.0466(11) 0.0436(11) 0.0075(9) 0.0103(9) 0.0093(9) C16 0.0259(9) 0.0448(10) 0.0414(10) 0.0083(8) -0.0022(8) 0.0081(8) C16A 0.0399(11) 0.0426(11) 0.0490(12) 0.0087(9) 0.0123(9) 0.0126(9) C17 0.0278(9) 0.0440(10) 0.0342(9) 0.0034(8) 0.0002(7) 0.0088(8) C17A 0.0394(11) 0.0446(11) 0.0464(11) 0.0119(9) 0.0105(9) 0.0123(9) C18 0.0258(9) 0.0327(8) 0.0355(9) 0.0086(7) 0.0035(7) 0.0070(7) C18A 0.0371(11) 0.0390(10) 0.0413(10) 0.0051(8) 0.0055(8) 0.0079(8) C19 0.0300(10) 0.0371(9) 0.0433(10) 0.0142(8) 0.0079(8) -0.0002(7) C19A 0.0341(11) 0.0433(11) 0.0806(17) 0.0076(11) 0.0094(11) -0.0004(9) C20 0.0259(9) 0.0378(10) 0.0515(12) 0.0079(8) 0.0026(8) 0.0020(7) C20A 0.0262(13) 0.0454(15) 0.0519(18) -0.0032(14) -0.0036(12) 0.0044(11) C22 0.0405(11) 0.0259(8) 0.0444(11) 0.0066(7) -0.0120(9) -0.0020(7) C22A 0.0571(16) 0.0755(17) 0.0752(18) 0.0330(14) -0.0214(13) -0.0026(13) C23 0.0479(12) 0.0287(9) 0.0370(10) 0.0001(7) -0.0053(8) 0.0104(8) C23A 0.0564(16) 0.0697(17) 0.100(2) 0.0444(16) -0.0188(15) 0.0083(13) O1 0.0575(10) 0.0416(8) 0.0542(9) 0.0114(7) 0.0019(8) 0.0066(7) O2 0.0510(10) 0.0887(12) 0.0376(8) 0.0221(8) 0.0120(7) 0.0054(9) O3 0.0557(11) 0.0506(10) 0.0989(15) 0.0327(10) 0.0197(10) 0.0142(8) O4 0.0589(12) 0.0711(13) 0.0697(12) 0.0215(10) 0.0123(10) 0.0124(9) O5 0.074(4) 0.100(4) 0.070(4) -0.003(3) 0.000(3) 0.032(4) O5A 0.094(5) 0.104(5) 0.066(4) 0.013(3) 0.001(4) -0.005(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 C2 1.472(2) . ? N1 C19 1.474(2) . ? N1 C18 1.477(2) . ? N1A C2A 1.467(3) . ? N1A C18A 1.475(3) . ? N1A C19A 1.480(3) . ? N10 C9 1.464(2) . ? N10 C11 1.469(2) . ? N10 C23 1.470(2) . ? N10A C9A 1.400(4) . ? N10A C11B 1.426(5) . ? N10A C23A 1.449(3) . ? N10A C11A 1.531(4) . ? N10A C9B 1.587(7) . ? O21 C20 1.421(2) . ? O21 C22 1.423(2) . ? O21A C22A 1.414(3) . ? O21A C20A 1.425(4) . ? O21B C22A 1.307(8) . ? O21B C20B 1.401(15) . ? C2 C3 1.517(2) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2A C3A 1.505(3) . ? C2A H2C 0.9800 . ? C2A H2D 0.9800 . ? C3 C4 1.530(3) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3A C4A 1.528(4) . ? C3A H3C 0.9800 . ? C3A H3D 0.9800 . ? C4 C5 1.462(3) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4A C5A 1.468(3) . ? C4A H4C 0.9800 . ? C4A H4D 0.9800 . ? C5 C6 1.188(3) . ? C5A C6A 1.171(3) . ? C6 C7 1.467(3) . ? C6A C7A 1.465(4) . ? C7 C8 1.537(3) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7A C8B 1.356(7) . ? C7A C8A 1.585(7) . ? C7A H7C 0.9800 . ? C7A H7D 0.9800 . ? C8 C9 1.521(2) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C8A C9A 1.581(7) . ? C8A H8C 0.9800 . ? C8A H8D 0.9800 . ? C9A H9C 0.9800 . ? C9A H9D 0.9800 . ? C8B C9B 1.432(9) . ? C8B H8E 0.9800 . ? C8B H8F 0.9800 . ? C9B H9E 0.9800 . ? C9B H9F 0.9800 . ? C11 C12 1.518(3) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C12 C13 1.533(3) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C11A C12A 1.545(6) . ? C11A H11C 0.9800 . ? C11A H11D 0.9800 . ? C12A C13A 1.461(7) . ? C12A H12C 0.9800 . ? C12A H12D 0.9800 . ? C11B C12B 1.472(9) . ? C11B H11E 0.9800 . ? C11B H11F 0.9800 . ? C12B C13A 1.539(9) . ? C12B H12E 0.9800 . ? C12B H12F 0.9800 . ? C13 C14 1.474(3) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13A C14A 1.471(3) . ? C13A H13C 0.9800 . ? C13A H13D 0.9800 . ? C14 C15 1.185(3) . ? C14A C15A 1.182(3) . ? C15 C16 1.468(3) . ? C15A C16A 1.474(3) . ? C16 C17 1.527(3) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16A C17A 1.521(3) . ? C16A H16C 0.9800 . ? C16A H16D 0.9800 . ? C17 C18 1.512(3) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17A C18A 1.513(3) . ? C17A H17C 0.9800 . ? C17A H17D 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18A H18C 0.9800 . ? C18A H18D 0.9800 . ? C19 C20 1.506(3) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19A C20B 1.481(13) . ? C19A C20A 1.504(4) . ? C19A H19C 0.9800 . ? C19A H19D 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20A H20C 0.9800 . ? C20A H20D 0.9800 . ? C20B H20E 0.9800 . ? C20B H20F 0.9800 . ? C22 C23 1.513(3) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22A C23A 1.454(4) . ? C22A H22C 0.9800 . ? C22A H22D 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23A H23C 0.9800 . ? C23A H23D 0.9800 . ? O1 H1A 0.94(3) . ? O1 H1B 0.83(3) . ? O2 H2E 0.79(3) . ? O2 H2F 1.45(3) . ? O3 H3E 0.94(3) . ? O3 H3F 0.86(3) . ? O4 H4E 0.83(3) . ? O4 H4F 0.83(3) . ? O5 O5A 0.671(7) . ? 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 N1 C19 113.37(14) . . ? C2 N1 C18 111.44(13) . . ? C19 N1 C18 111.58(14) . . ? C2A N1A C18A 111.79(16) . . ? C2A N1A C19A 113.11(17) . . ? C18A N1A C19A 110.27(17) . . ? C9 N10 C11 112.76(14) . . ? C9 N10 C23 110.69(15) . . ? C11 N10 C23 111.97(15) . . ? C9A N10A C11B 74.6(3) . . ? C9A N10A C23A 124.4(3) . . ? C11B N10A C23A 127.1(3) . . ? C9A N10A C11A 111.0(3) . . ? C11B N10A C11A 36.7(3) . . ? C23A N10A C11A 100.8(2) . . ? C9A N10A C9B 32.7(3) . . ? C11B N10A C9B 104.7(4) . . ? C23A N10A C9B 95.5(3) . . ? C11A N10A C9B 138.3(3) . . ? C20 O21 C22 111.40(14) . . ? C22A O21A C20A 111.0(2) . . ? C22A O21B C20B 121.6(8) . . ? N1 C2 C3 113.66(14) . . ? N1 C2 H2A 108.8 . . ? C3 C2 H2A 108.8 . . ? N1 C2 H2B 108.8 . . ? C3 C2 H2B 108.8 . . ? H2A C2 H2B 107.7 . . ? N1A C2A C3A 115.02(19) . . ? N1A C2A H2C 108.5 . . ? C3A C2A H2C 108.5 . . ? N1A C2A H2D 108.5 . . ? C3A C2A H2D 108.5 . . ? H2C C2A H2D 107.5 . . ? C2 C3 C4 111.84(15) . . ? C2 C3 H3A 109.2 . . ? C4 C3 H3A 109.2 . . ? C2 C3 H3B 109.2 . . ? C4 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? C2A C3A C4A 111.9(2) . . ? C2A C3A H3C 109.2 . . ? C4A C3A H3C 109.2 . . ? C2A C3A H3D 109.2 . . ? C4A C3A H3D 109.2 . . ? H3C C3A H3D 107.9 . . ? C5 C4 C3 113.15(15) . . ? C5 C4 H4A 108.9 . . ? C3 C4 H4A 108.9 . . ? C5 C4 H4B 108.9 . . ? C3 C4 H4B 108.9 . . ? H4A C4 H4B 107.8 . . ? C5A C4A C3A 112.6(2) . . ? C5A C4A H4C 109.1 . . ? C3A C4A H4C 109.1 . . ? C5A C4A H4D 109.1 . . ? C3A C4A H4D 109.1 . . ? H4C C4A H4D 107.8 . . ? C6 C5 C4 178.5(2) . . ? C6A C5A C4A 177.8(2) . . ? C5 C6 C7 177.8(2) . . ? C5A C6A C7A 175.8(3) . . ? C6 C7 C8 112.17(15) . . ? C6 C7 H7A 109.2 . . ? C8 C7 H7A 109.2 . . ? C6 C7 H7B 109.2 . . ? C8 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? C8B C7A C6A 115.1(3) . . ? C8B C7A C8A 31.8(3) . . ? C6A C7A C8A 112.2(3) . . ? C8B C7A H7C 79.0 . . ? C6A C7A H7C 109.2 . . ? C8A C7A H7C 109.2 . . ? C8B C7A H7D 129.8 . . ? C6A C7A H7D 109.2 . . ? C8A C7A H7D 109.2 . . ? H7C C7A H7D 107.9 . . ? C9 C8 C7 109.92(16) . . ? C9 C8 H8A 109.7 . . ? C7 C8 H8A 109.7 . . ? C9 C8 H8B 109.7 . . ? C7 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? N10 C9 C8 115.43(16) . . ? N10 C9 H9A 108.4 . . ? C8 C9 H9A 108.4 . . ? N10 C9 H9B 108.4 . . ? C8 C9 H9B 108.4 . . ? H9A C9 H9B 107.5 . . ? C9A C8A C7A 112.4(4) . . ? C9A C8A H8C 109.1 . . ? C7A C8A H8C 109.1 . . ? C9A C8A H8D 109.1 . . ? C7A C8A H8D 109.1 . . ? H8C C8A H8D 107.9 . . ? N10A C9A C8A 109.5(4) . . ? N10A C9A H9C 109.8 . . ? C8A C9A H9C 109.8 . . ? N10A C9A H9D 109.8 . . ? C8A C9A H9D 109.8 . . ? H9C C9A H9D 108.2 . . ? C7A C8B C9B 118.5(6) . . ? C7A C8B H8E 107.7 . . ? C9B C8B H8E 107.7 . . ? C7A C8B H8F 107.7 . . ? C9B C8B H8F 107.7 . . ? H8E C8B H8F 107.1 . . ? C8B C9B N10A 119.1(5) . . ? C8B C9B H9E 107.5 . . ? N10A C9B H9E 107.5 . . ? C8B C9B H9F 107.5 . . ? N10A C9B H9F 107.5 . . ? H9E C9B H9F 107.0 . . ? N10 C11 C12 112.71(15) . . ? N10 C11 H11A 109.0 . . ? C12 C11 H11A 109.0 . . ? N10 C11 H11B 109.0 . . ? C12 C11 H11B 109.0 . . ? H11A C11 H11B 107.8 . . ? C11 C12 C13 112.60(16) . . ? C11 C12 H12A 109.1 . . ? C13 C12 H12A 109.1 . . ? C11 C12 H12B 109.1 . . ? C13 C12 H12B 109.1 . . ? H12A C12 H12B 107.8 . . ? N10A C11A C12A 113.7(3) . . ? N10A C11A H11C 108.8 . . ? C12A C11A H11C 108.8 . . ? N10A C11A H11D 108.8 . . ? C12A C11A H11D 108.8 . . ? H11C C11A H11D 107.7 . . ? C13A C12A C11A 111.1(4) . . ? C13A C12A H12C 109.4 . . ? C11A C12A H12C 109.4 . . ? C13A C12A H12D 109.4 . . ? C11A C12A H12D 109.4 . . ? H12C C12A H12D 108.0 . . ? N10A C11B C12B 110.5(5) . . ? N10A C11B H11E 109.5 . . ? C12B C11B H11E 109.5 . . ? N10A C11B H11F 109.5 . . ? C12B C11B H11F 109.5 . . ? H11E C11B H11F 108.1 . . ? C11B C12B C13A 123.3(5) . . ? C11B C12B H12E 106.5 . . ? C13A C12B H12E 106.5 . . ? C11B C12B H12F 106.5 . . ? C13A C12B H12F 106.5 . . ? H12E C12B H12F 106.5 . . ? C14 C13 C12 113.59(17) . . ? C14 C13 H13A 108.8 . . ? C12 C13 H13A 108.8 . . ? C14 C13 H13B 108.8 . . ? C12 C13 H13B 108.8 . . ? H13A C13 H13B 107.7 . . ? C12A C13A C14A 117.8(3) . . ? C12A C13A C12B 26.3(3) . . ? C14A C13A C12B 111.2(4) . . ? C12A C13A H13C 107.9 . . ? C14A C13A H13C 107.9 . . ? C12B C13A H13C 131.3 . . ? C12A C13A H13D 107.9 . . ? C14A C13A H13D 107.9 . . ? C12B C13A H13D 87.3 . . ? H13C C13A H13D 107.2 . . ? C15 C14 C13 177.88(19) . . ? C15A C14A C13A 177.4(2) . . ? C14 C15 C16 176.35(19) . . ? C14A C15A C16A 177.3(2) . . ? C15 C16 C17 111.38(15) . . ? C15 C16 H16A 109.4 . . ? C17 C16 H16A 109.4 . . ? C15 C16 H16B 109.4 . . ? C17 C16 H16B 109.4 . . ? H16A C16 H16B 108.0 . . ? C15A C16A C17A 113.06(17) . . ? C15A C16A H16C 109.0 . . ? C17A C16A H16C 109.0 . . ? C15A C16A H16D 109.0 . . ? C17A C16A H16D 109.0 . . ? H16C C16A H16D 107.8 . . ? C18 C17 C16 110.95(15) . . ? C18 C17 H17A 109.4 . . ? C16 C17 H17A 109.4 . . ? C18 C17 H17B 109.4 . . ? C16 C17 H17B 109.4 . . ? H17A C17 H17B 108.0 . . ? C18A C17A C16A 111.81(18) . . ? C18A C17A H17C 109.3 . . ? C16A C17A H17C 109.3 . . ? C18A C17A H17D 109.3 . . ? C16A C17A H17D 109.3 . . ? H17C C17A H17D 107.9 . . ? N1 C18 C17 113.85(15) . . ? N1 C18 H18A 108.8 . . ? C17 C18 H18A 108.8 . . ? N1 C18 H18B 108.8 . . ? C17 C18 H18B 108.8 . . ? H18A C18 H18B 107.7 . . ? N1A C18A C17A 114.51(17) . . ? N1A C18A H18C 108.6 . . ? C17A C18A H18C 108.6 . . ? N1A C18A H18D 108.6 . . ? C17A C18A H18D 108.6 . . ? H18C C18A H18D 107.6 . . ? N1 C19 C20 118.65(16) . . ? N1 C19 H19A 107.7 . . ? C20 C19 H19A 107.7 . . ? N1 C19 H19B 107.7 . . ? C20 C19 H19B 107.7 . . ? H19A C19 H19B 107.1 . . ? N1A C19A C20B 120.0(6) . . ? N1A C19A C20A 118.7(2) . . ? C20B C19A C20A 28.1(5) . . ? N1A C19A H19C 107.6 . . ? C20B C19A H19C 81.4 . . ? C20A C19A H19C 107.6 . . ? N1A C19A H19D 107.6 . . ? C20B C19A H19D 126.5 . . ? C20A C19A H19D 107.6 . . ? H19C C19A H19D 107.1 . . ? O21 C20 C19 112.03(15) . . ? O21 C20 H20A 109.2 . . ? C19 C20 H20A 109.2 . . ? O21 C20 H20B 109.2 . . ? C19 C20 H20B 109.2 . . ? H20A C20 H20B 107.9 . . ? O21A C20A C19A 113.4(2) . . ? O21A C20A H20C 108.9 . . ? C19A C20A H20C 108.9 . . ? O21A C20A H20D 108.9 . . ? C19A C20A H20D 108.9 . . ? H20C C20A H20D 107.7 . . ? O21B C20B C19A 119.6(10) . . ? O21B C20B H20E 107.4 . . ? C19A C20B H20E 107.4 . . ? O21B C20B H20F 107.4 . . ? C19A C20B H20F 107.4 . . ? H20E C20B H20F 107.0 . . ? O21 C22 C23 112.21(15) . . ? O21 C22 H22A 109.2 . . ? C23 C22 H22A 109.2 . . ? O21 C22 H22B 109.2 . . ? C23 C22 H22B 109.2 . . ? H22A C22 H22B 107.9 . . ? O21B C22A O21A 25.7(3) . . ? O21B C22A C23A 127.1(4) . . ? O21A C22A C23A 116.5(2) . . ? O21B C22A H22C 117.8 . . ? O21A C22A H22C 108.2 . . ? C23A C22A H22C 108.2 . . ? O21B C22A H22D 82.5 . . ? O21A C22A H22D 108.2 . . ? C23A C22A H22D 108.2 . . ? H22C C22A H22D 107.3 . . ? N10 C23 C22 118.49(15) . . ? N10 C23 H23A 107.7 . . ? C22 C23 H23A 107.7 . . ? N10 C23 H23B 107.7 . . ? C22 C23 H23B 107.7 . . ? H23A C23 H23B 107.1 . . ? N10A C23A C22A 123.6(2) . . ? N10A C23A H23C 106.4 . . ? C22A C23A H23C 106.4 . . ? N10A C23A H23D 106.4 . . ? C22A C23A H23D 106.4 . . ? H23C C23A H23D 106.5 . . ? H1A O1 H1B 99(2) . . ? H2E O2 H2F 114(2) . . ? H3E O3 H3F 100(3) . . ? H4E O4 H4F 97(3) . . ? 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 C19 N1 C2 C3 -60.3(2) . . . . ? C18 N1 C2 C3 172.79(14) . . . . ? C18A N1A C2A C3A -169.7(2) . . . . ? C19A N1A C2A C3A 65.2(3) . . . . ? N1 C2 C3 C4 -177.45(15) . . . . ? N1A C2A C3A C4A 171.0(2) . . . . ? C2 C3 C4 C5 -58.4(2) . . . . ? C2A C3A C4A C5A 56.1(3) . . . . ? C3 C4 C5 C6 91(7) . . . . ? C3A C4A C5A C6A -43(8) . . . . ? C4 C5 C6 C7 -41(11) . . . . ? C4A C5A C6A C7A 33(11) . . . . ? C5 C6 C7 C8 -5(5) . . . . ? C5A C6A C7A C8B -30(4) . . . . ? C5A C6A C7A C8A 5(4) . . . . ? C6 C7 C8 C9 -62.3(2) . . . . ? C11 N10 C9 C8 -67.1(2) . . . . ? C23 N10 C9 C8 166.61(15) . . . . ? C7 C8 C9 N10 172.02(15) . . . . ? C8B C7A C8A C9A 44.0(6) . . . . ? C6A C7A C8A C9A -58.2(6) . . . . ? C11B N10A C9A C8A 173.5(4) . . . . ? C23A N10A C9A C8A -61.8(4) . . . . ? C11A N10A C9A C8A 177.8(4) . . . . ? C9B N10A C9A C8A -30.4(5) . . . . ? C7A C8A C9A N10A -173.8(4) . . . . ? C6A C7A C8B C9B 54.2(8) . . . . ? C8A C7A C8B C9B -37.9(6) . . . . ? C7A C8B C9B N10A -175.9(4) . . . . ? C9A N10A C9B C8B 52.7(6) . . . . ? C11B N10A C9B C8B 76.5(6) . . . . ? C23A N10A C9B C8B -152.8(6) . . . . ? C11A N10A C9B C8B 94.3(6) . . . . ? C9 N10 C11 C12 158.71(16) . . . . ? C23 N10 C11 C12 -75.7(2) . . . . ? N10 C11 C12 C13 -172.66(16) . . . . ? C9A N10A C11A C12A -63.4(4) . . . . ? C11B N10A C11A C12A -56.3(5) . . . . ? C23A N10A C11A C12A 163.0(3) . . . . ? C9B N10A C11A C12A -85.9(6) . . . . ? N10A C11A C12A C13A 170.7(3) . . . . ? C9A N10A C11B C12B -153.1(6) . . . . ? C23A N10A C11B C12B 85.1(6) . . . . ? C11A N10A C11B C12B 33.8(5) . . . . ? C9B N10A C11B C12B -166.1(5) . . . . ? N10A C11B C12B C13A 177.2(6) . . . . ? C11 C12 C13 C14 -52.9(2) . . . . ? C11A C12A C13A C14A -57.9(5) . . . . ? C11A C12A C13A C12B 23.9(7) . . . . ? C11B C12B C13A C12A -67.6(10) . . . . ? C11B C12B C13A C14A 42.5(9) . . . . ? C12 C13 C14 C15 16(5) . . . . ? C12A C13A C14A C15A 8(6) . . . . ? C12B C13A C14A C15A -20(6) . . . . ? C13 C14 C15 C16 27(8) . . . . ? C13A C14A C15A C16A 2(10) . . . . ? C14 C15 C16 C17 7(3) . . . . ? C14A C15A C16A C17A -12(5) . . . . ? C15 C16 C17 C18 -64.0(2) . . . . ? C15A C16A C17A C18A 60.8(2) . . . . ? C2 N1 C18 C17 -69.61(19) . . . . ? C19 N1 C18 C17 162.54(15) . . . . ? C16 C17 C18 N1 176.88(15) . . . . ? C2A N1A C18A C17A 68.0(2) . . . . ? C19A N1A C18A C17A -165.31(17) . . . . ? C16A C17A C18A N1A -178.68(16) . . . . ? C2 N1 C19 C20 -45.8(2) . . . . ? C18 N1 C19 C20 81.0(2) . . . . ? C2A N1A C19A C20B 52.6(7) . . . . ? C18A N1A C19A C20B -73.4(7) . . . . ? C2A N1A C19A C20A 84.9(3) . . . . ? C18A N1A C19A C20A -41.1(3) . . . . ? C22 O21 C20 C19 -172.29(15) . . . . ? N1 C19 C20 O21 -54.9(2) . . . . ? C22A O21A C20A C19A 175.9(2) . . . . ? N1A C19A C20A O21A -57.5(3) . . . . ? C20B C19A C20A O21A 43.1(11) . . . . ? C22A O21B C20B C19A 171.9(8) . . . . ? N1A C19A C20B O21B 42.3(14) . . . . ? C20A C19A C20B O21B -53.2(10) . . . . ? C20 O21 C22 C23 -154.99(15) . . . . ? C20B O21B C22A O21A 49.9(10) . . . . ? C20B O21B C22A C23A 123.6(9) . . . . ? C20A O21A C22A O21B -49.4(9) . . . . ? C20A O21A C22A C23A -170.6(3) . . . . ? C9 N10 C23 C22 35.8(2) . . . . ? C11 N10 C23 C22 -90.9(2) . . . . ? O21 C22 C23 N10 63.2(2) . . . . ? C9A N10A C23A C22A -67.7(4) . . . . ? C11B N10A C23A C22A 28.9(5) . . . . ? C11A N10A C23A C22A 57.3(4) . . . . ? C9B N10A C23A C22A -84.1(4) . . . . ? O21B C22A C23A N10A 14.9(7) . . . . ? O21A C22A C23A N10A 42.5(5) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.98 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.251 _refine_diff_density_min -0.315 _refine_diff_density_rms 0.052 data_th4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; (44) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H36 N2 O2' _chemical_formula_weight 360.53 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' '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 8.97060(10) _cell_length_b 20.6147(3) _cell_length_c 11.46140(10) _cell_angle_alpha 90.00 _cell_angle_beta 94.86 _cell_angle_gamma 90.00 _cell_volume 2111.90(4) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description polyhedron _exptl_crystal_colour colorless _exptl_crystal_size_max .40 _exptl_crystal_size_mid .24 _exptl_crystal_size_min .20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.134 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38.' _exptl_absorpt_correction_T_min 0.70 _exptl_absorpt_correction_T_max 1.00 _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15586 _diffrn_reflns_av_R_equivalents 0.0246 _diffrn_reflns_av_sigmaI/netI 0.0203 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 25.60 _reflns_number_total 3668 _reflns_number_gt 3088 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0425P)^2^+0.4847P] 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 ride _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3668 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0455 _refine_ls_R_factor_gt 0.0352 _refine_ls_wR_factor_ref 0.0904 _refine_ls_wR_factor_gt 0.0842 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.015 _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 0.23433(11) 0.14523(5) 0.64360(9) 0.0296(2) Uani 1 1 d . . . C1 C 0.09077(14) 0.17896(7) 0.63193(12) 0.0378(3) Uani 1 1 d . . . H1A H 0.0572 0.1860 0.7110 0.045 Uiso 1 1 calc R . . H1B H 0.0161 0.1507 0.5884 0.045 Uiso 1 1 calc R . . C2 C 0.09385(15) 0.24380(7) 0.56985(12) 0.0420(3) Uani 1 1 d . . . H2A H 0.1457 0.2757 0.6236 0.050 Uiso 1 1 calc R . . H2B H -0.0103 0.2590 0.5522 0.050 Uiso 1 1 calc R . . C3 C 0.17139(16) 0.24234(7) 0.45588(12) 0.0398(3) Uani 1 1 d . . . H3A H 0.1714 0.2867 0.4229 0.048 Uiso 1 1 calc R . . H3B H 0.2769 0.2291 0.4740 0.048 Uiso 1 1 calc R . . C4 C 0.10136(14) 0.19826(7) 0.36699(12) 0.0359(3) Uani 1 1 d . . . C5 C 0.04580(14) 0.16189(7) 0.29504(12) 0.0359(3) Uani 1 1 d . . . C6 C -0.01493(15) 0.11715(7) 0.20347(12) 0.0396(3) Uani 1 1 d . . . H6A H -0.1255 0.1180 0.2001 0.048 Uiso 1 1 calc R . . H6B H 0.0182 0.0725 0.2242 0.048 Uiso 1 1 calc R . . C7 C 0.03452(15) 0.13420(7) 0.08251(12) 0.0421(3) Uani 1 1 d . . . H7A H -0.0039 0.1008 0.0257 0.051 Uiso 1 1 calc R . . H7B H -0.0107 0.1762 0.0571 0.051 Uiso 1 1 calc R . . C8 C 0.20349(15) 0.13883(6) 0.08013(11) 0.0374(3) Uani 1 1 d . . . H8A H 0.2277 0.1458 -0.0016 0.045 Uiso 1 1 calc R . . H8B H 0.2400 0.1770 0.1266 0.045 Uiso 1 1 calc R . . N2 N 0.28203(11) 0.08084(5) 0.12662(9) 0.0300(2) Uani 1 1 d . . . C9 C 0.27122(15) 0.02762(6) 0.04166(11) 0.0365(3) Uani 1 1 d . . . H9A H 0.3456 0.0349 -0.0161 0.044 Uiso 1 1 calc R . . H9B H 0.1707 0.0286 -0.0012 0.044 Uiso 1 1 calc R . . C10 C 0.29697(15) -0.03937(6) 0.09522(11) 0.0352(3) Uani 1 1 d . . . H10A H 0.4005 -0.0417 0.1325 0.042 Uiso 1 1 calc R . . H10B H 0.2873 -0.0721 0.0319 0.042 Uiso 1 1 calc R . . C11 C 0.18820(15) -0.05652(6) 0.18655(11) 0.0350(3) Uani 1 1 d . . . H11A H 0.0867 -0.0418 0.1575 0.042 Uiso 1 1 calc R . . H11B H 0.1849 -0.1043 0.1947 0.042 Uiso 1 1 calc R . . C12 C 0.22639(14) -0.02801(6) 0.30253(11) 0.0323(3) Uani 1 1 d . . . C13 C 0.26089(15) -0.00626(6) 0.39745(11) 0.0329(3) Uani 1 1 d . . . C14 C 0.30310(15) 0.02263(6) 0.51240(11) 0.0355(3) Uani 1 1 d . . . H14A H 0.3505 0.0653 0.5008 0.043 Uiso 1 1 calc R . . H14B H 0.3787 -0.0055 0.5551 0.043 Uiso 1 1 calc R . . C15 C 0.17318(15) 0.03212(6) 0.58774(11) 0.0369(3) Uani 1 1 d . . . H15A H 0.0857 0.0495 0.5391 0.044 Uiso 1 1 calc R . . H15B H 0.1446 -0.0101 0.6203 0.044 Uiso 1 1 calc R . . C16 C 0.21730(15) 0.07892(6) 0.68707(11) 0.0364(3) Uani 1 1 d . . . H16A H 0.1398 0.0784 0.7436 0.044 Uiso 1 1 calc R . . H16B H 0.3128 0.0646 0.7287 0.044 Uiso 1 1 calc R . . C17 C 0.35501(14) 0.18115(6) 0.70796(11) 0.0322(3) Uani 1 1 d . . . H17A H 0.3533 0.1722 0.7927 0.039 Uiso 1 1 calc R . . H17B H 0.3384 0.2282 0.6957 0.039 Uiso 1 1 calc R . . C18 C 0.50660(14) 0.16298(6) 0.66941(11) 0.0317(3) Uani 1 1 d . . . H18A H 0.5862 0.1859 0.7184 0.038 Uiso 1 1 calc R . . H18B H 0.5229 0.1157 0.6791 0.038 Uiso 1 1 calc R . . O1 O 0.51321(9) 0.18049(4) 0.54973(7) 0.0315(2) Uani 1 1 d . . . C19 C 0.65984(13) 0.17335(6) 0.51326(11) 0.0313(3) Uani 1 1 d . . . H19A H 0.6941 0.1281 0.5269 0.038 Uiso 1 1 calc R . . H19B H 0.7294 0.2023 0.5603 0.038 Uiso 1 1 calc R . . C20 C 0.66260(14) 0.18962(6) 0.38579(11) 0.0336(3) Uani 1 1 d . . . H20A H 0.5982 0.2280 0.3683 0.040 Uiso 1 1 calc R . . H20B H 0.7660 0.2019 0.3709 0.040 Uiso 1 1 calc R . . O2 O 0.61435(9) 0.13897(5) 0.30736(8) 0.0395(2) Uani 1 1 d . . . C21 C 0.45782(13) 0.13616(6) 0.27515(11) 0.0334(3) Uani 1 1 d . . . H21A H 0.4174 0.1802 0.2585 0.040 Uiso 1 1 calc R . . H21B H 0.4048 0.1168 0.3390 0.040 Uiso 1 1 calc R . . C22 C 0.43833(14) 0.09423(6) 0.16637(11) 0.0338(3) Uani 1 1 d . . . H22A H 0.4865 0.1161 0.1025 0.041 Uiso 1 1 calc R . . H22B H 0.4908 0.0525 0.1825 0.041 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 0.0280(5) 0.0349(6) 0.0261(6) -0.0055(4) 0.0036(4) -0.0027(4) C1 0.0287(7) 0.0510(8) 0.0346(7) -0.0134(6) 0.0074(6) 0.0006(6) C2 0.0366(8) 0.0441(8) 0.0443(8) -0.0155(6) -0.0026(6) 0.0109(6) C3 0.0410(8) 0.0376(7) 0.0393(8) -0.0009(6) -0.0050(6) 0.0046(6) C4 0.0332(7) 0.0398(7) 0.0344(8) 0.0007(6) 0.0011(6) 0.0089(6) C5 0.0303(7) 0.0408(7) 0.0366(8) 0.0000(6) 0.0037(6) 0.0085(6) C6 0.0302(7) 0.0440(8) 0.0445(8) -0.0103(6) 0.0026(6) 0.0016(6) C7 0.0426(8) 0.0457(8) 0.0360(8) -0.0069(6) -0.0082(6) 0.0075(6) C8 0.0461(8) 0.0393(7) 0.0264(7) 0.0047(6) 0.0020(6) -0.0005(6) N2 0.0323(6) 0.0328(6) 0.0250(6) -0.0007(4) 0.0033(4) -0.0019(4) C9 0.0386(7) 0.0464(8) 0.0252(7) -0.0057(6) 0.0063(5) -0.0041(6) C10 0.0353(7) 0.0383(7) 0.0326(7) -0.0123(6) 0.0062(6) -0.0004(6) C11 0.0376(7) 0.0326(7) 0.0348(7) -0.0063(6) 0.0040(6) -0.0039(6) C12 0.0354(7) 0.0285(6) 0.0335(8) 0.0011(6) 0.0064(6) 0.0020(5) C13 0.0389(7) 0.0271(6) 0.0334(8) 0.0010(6) 0.0071(6) 0.0010(5) C14 0.0397(7) 0.0366(7) 0.0304(7) -0.0024(5) 0.0046(6) -0.0028(6) C15 0.0407(8) 0.0365(7) 0.0343(7) -0.0023(6) 0.0087(6) -0.0107(6) C16 0.0407(8) 0.0432(8) 0.0265(7) -0.0007(6) 0.0104(6) -0.0079(6) C17 0.0336(7) 0.0388(7) 0.0243(7) -0.0067(5) 0.0028(5) -0.0028(5) C18 0.0303(6) 0.0389(7) 0.0253(6) -0.0013(5) -0.0013(5) -0.0017(5) O1 0.0243(4) 0.0431(5) 0.0273(5) 0.0033(4) 0.0033(3) 0.0013(4) C19 0.0226(6) 0.0347(7) 0.0368(7) 0.0001(5) 0.0024(5) -0.0020(5) C20 0.0270(6) 0.0378(7) 0.0365(7) 0.0011(6) 0.0050(5) -0.0080(5) O2 0.0289(5) 0.0487(6) 0.0408(6) -0.0107(4) 0.0012(4) 0.0007(4) C21 0.0275(6) 0.0428(7) 0.0306(7) -0.0006(6) 0.0068(5) -0.0045(5) C22 0.0321(7) 0.0364(7) 0.0339(7) -0.0021(6) 0.0084(6) -0.0038(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 C17 1.4591(15) . ? N1 C1 1.4597(16) . ? N1 C16 1.4674(16) . ? C1 C2 1.516(2) . ? C2 C3 1.531(2) . ? C3 C4 1.4662(19) . ? C4 C5 1.1921(18) . ? C5 C6 1.4670(19) . ? C6 C7 1.532(2) . ? C7 C8 1.5213(19) . ? C8 N2 1.4649(16) . ? N2 C22 1.4634(16) . ? N2 C9 1.4646(16) . ? C9 C10 1.5210(19) . ? C10 C11 1.5316(18) . ? C11 C12 1.4672(18) . ? C12 C13 1.1931(18) . ? C13 C14 1.4661(18) . ? C14 C15 1.5208(18) . ? C15 C16 1.5189(18) . ? C17 C18 1.5121(17) . ? C18 O1 1.4245(15) . ? O1 C19 1.4212(14) . ? C19 C20 1.5013(18) . ? C20 O2 1.4212(15) . ? O2 C21 1.4224(15) . ? C21 C22 1.5149(18) . ? 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 C17 N1 C1 114.56(10) . . ? C17 N1 C16 113.28(10) . . ? C1 N1 C16 111.01(10) . . ? N1 C1 C2 114.34(11) . . ? C1 C2 C3 114.25(11) . . ? C4 C3 C2 113.96(12) . . ? C5 C4 C3 179.20(14) . . ? C4 C5 C6 176.90(14) . . ? C5 C6 C7 112.63(12) . . ? C8 C7 C6 113.32(11) . . ? N2 C8 C7 113.05(11) . . ? C22 N2 C9 110.86(10) . . ? C22 N2 C8 112.20(10) . . ? C9 N2 C8 111.51(10) . . ? N2 C9 C10 114.36(10) . . ? C9 C10 C11 113.68(11) . . ? C12 C11 C10 114.42(11) . . ? C13 C12 C11 177.95(14) . . ? C12 C13 C14 178.11(13) . . ? C13 C14 C15 114.24(11) . . ? C16 C15 C14 110.11(11) . . ? N1 C16 C15 111.42(10) . . ? N1 C17 C18 111.95(10) . . ? O1 C18 C17 109.29(10) . . ? C19 O1 C18 111.83(9) . . ? O1 C19 C20 110.79(10) . . ? O2 C20 C19 114.96(10) . . ? C20 O2 C21 115.80(9) . . ? O2 C21 C22 106.23(10) . . ? N2 C22 C21 113.87(10) . . ? _diffrn_measured_fraction_theta_max 0.924 _diffrn_reflns_theta_full 25.60 _diffrn_measured_fraction_theta_full 0.924 _refine_diff_density_max 0.135 _refine_diff_density_min -0.156 _refine_diff_density_rms 0.035 data_765tri _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,10-Diazabicyclo[8.8.6]tetracosa-5,14,21-triyne (46) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H32 N2' _chemical_formula_weight 324.50 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 9.569(1) _cell_length_b 12.697(2) _cell_length_c 16.052(5) _cell_angle_alpha 90.0 _cell_angle_beta 98.82(2) _cell_angle_gamma 90.0 _cell_volume 1927.2(7) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.1 _cell_measurement_theta_max 18.0 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.118 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.065 _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 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type NONIUS_CAD4 _diffrn_measurement_method \w2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 10 _diffrn_reflns_number 4910 _diffrn_reflns_av_R_equivalents 0.0247 _diffrn_reflns_av_sigmaI/netI 0.0459 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 27.97 _reflns_number_total 4641 _reflns_number_gt 2962 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0560P)^2^+0.1889P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4641 _refine_ls_number_parameters 345 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.092 _refine_ls_R_factor_gt 0.039 _refine_ls_wR_factor_ref 0.109 _refine_ls_wR_factor_gt 0.093 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.06358(10) 0.08808(9) 0.19766(6) 0.0280(2) Uani 1 1 d . . . N10 N 0.64509(11) 0.15646(9) 0.24657(7) 0.0319(3) Uani 1 1 d . . . C2 C 0.14510(14) 0.06319(12) 0.27998(8) 0.0317(3) Uani 1 1 d . . . C3 C 0.06819(14) 0.08508(13) 0.35398(9) 0.0356(3) Uani 1 1 d . . . C4 C 0.15528(16) 0.04723(13) 0.43681(9) 0.0376(3) Uani 1 1 d . . . C5 C 0.29925(15) 0.09054(11) 0.45238(8) 0.0339(3) Uani 1 1 d . . . C6 C 0.41711(15) 0.12307(11) 0.46253(8) 0.0336(3) Uani 1 1 d . . . C7 C 0.56373(15) 0.16151(12) 0.47338(8) 0.0352(3) Uani 1 1 d . . . C8 C 0.64148(15) 0.13371(13) 0.40013(8) 0.0354(3) Uani 1 1 d . . . C9 C 0.57663(14) 0.18721(12) 0.31852(8) 0.0323(3) Uani 1 1 d . . . C11 C 0.59993(15) 0.05043(12) 0.21765(9) 0.0351(3) Uani 1 1 d . . . C12 C 0.67660(15) 0.00713(13) 0.14924(9) 0.0385(3) Uani 1 1 d . . . C13 C 0.62313(15) -0.10282(13) 0.12053(10) 0.0410(4) Uani 1 1 d . . . C14 C 0.47018(14) -0.10461(11) 0.08960(8) 0.0332(3) Uani 1 1 d . . . C15 C 0.34616(14) -0.10364(11) 0.06726(8) 0.0304(3) Uani 1 1 d . . . C16 C 0.19210(14) -0.10465(12) 0.04135(8) 0.0317(3) Uani 1 1 d . . . C17 C 0.10908(14) -0.06485(11) 0.10940(8) 0.0293(3) Uani 1 1 d . . . C18 C 0.13774(13) 0.05042(11) 0.12959(8) 0.0283(3) Uani 1 1 d . . . C19 C 0.01795(13) 0.19766(11) 0.18905(9) 0.0309(3) Uani 1 1 d . . . C20 C 0.12781(15) 0.28494(12) 0.21535(9) 0.0358(3) Uani 1 1 d . . . C21 C 0.25792(13) 0.27551(10) 0.17853(8) 0.0300(3) Uani 1 1 d . . . C22 C 0.36538(13) 0.26329(11) 0.15157(8) 0.0315(3) Uani 1 1 d . . . C23 C 0.49378(15) 0.23997(15) 0.11582(9) 0.0400(4) Uani 1 1 d . . . C24 C 0.63200(14) 0.23521(14) 0.17928(9) 0.0384(3) Uani 1 1 d . . . H2A H 0.2361(16) 0.1035(12) 0.2887(9) 0.036(4) Uiso 1 1 d . . . H2B H 0.1700(16) -0.0119(14) 0.2795(10) 0.044(4) Uiso 1 1 d . . . H3A H 0.0485(17) 0.1621(14) 0.3593(10) 0.048(5) Uiso 1 1 d . . . H3B H -0.0233(16) 0.0476(12) 0.3458(9) 0.040(4) Uiso 1 1 d . . . H4A H 0.1616(16) -0.0317(14) 0.4359(10) 0.046(4) Uiso 1 1 d . . . H4B H 0.1048(16) 0.0663(13) 0.4852(10) 0.050(5) Uiso 1 1 d . . . H7B H 0.6149(15) 0.1305(12) 0.5264(10) 0.042(4) Uiso 1 1 d . . . H7A H 0.5623(16) 0.2384(14) 0.4800(10) 0.044(4) Uiso 1 1 d . . . H8A H 0.7411(17) 0.1569(13) 0.4156(10) 0.044(4) Uiso 1 1 d . . . H8B H 0.6403(16) 0.0556(13) 0.3933(9) 0.042(4) Uiso 1 1 d . . . H9A H 0.4731(15) 0.1717(11) 0.3080(8) 0.032(4) Uiso 1 1 d . . . H9B H 0.5890(16) 0.2662(13) 0.3260(9) 0.042(4) Uiso 1 1 d . . . H11A H 0.6208(15) 0.0014(13) 0.2681(10) 0.043(4) Uiso 1 1 d . . . H11B H 0.4958(15) 0.0489(11) 0.1965(9) 0.037(4) Uiso 1 1 d . . . H12A H 0.6631(15) 0.0567(12) 0.0996(10) 0.038(4) Uiso 1 1 d . . . H12B H 0.7781(17) 0.0040(13) 0.1696(10) 0.047(4) Uiso 1 1 d . . . H13A H 0.6468(17) -0.1532(14) 0.1697(11) 0.054(5) Uiso 1 1 d . . . H13B H 0.6746(17) -0.1292(14) 0.0753(11) 0.054(5) Uiso 1 1 d . . . H16B H 0.1688(15) -0.0614(13) -0.0093(10) 0.040(4) Uiso 1 1 d . . . H16A H 0.1641(16) -0.1755(13) 0.0253(10) 0.045(4) Uiso 1 1 d . . . H17A H 0.0075(15) -0.0744(11) 0.0895(9) 0.032(4) Uiso 1 1 d . . . H17B H 0.1306(14) -0.1102(12) 0.1621(9) 0.034(4) Uiso 1 1 d . . . H18B H 0.1057(14) 0.0950(12) 0.0792(9) 0.032(4) Uiso 1 1 d . . . H18A H 0.2410(14) 0.0595(11) 0.1436(8) 0.028(3) Uiso 1 1 d . . . H19B H -0.0253(14) 0.2086(12) 0.1278(9) 0.035(4) Uiso 1 1 d . . . H19A H -0.0584(15) 0.2086(12) 0.2237(9) 0.034(4) Uiso 1 1 d . . . H20A H 0.0796(17) 0.3522(14) 0.2003(10) 0.052(5) Uiso 1 1 d . . . H20B H 0.1540(16) 0.2817(13) 0.2784(10) 0.044(4) Uiso 1 1 d . . . H23B H 0.4785(17) 0.1736(15) 0.0839(10) 0.051(5) Uiso 1 1 d . . . H23A H 0.5072(17) 0.2962(14) 0.0745(10) 0.052(5) Uiso 1 1 d . . . H24B H 0.6490(16) 0.3062(14) 0.2070(9) 0.043(4) Uiso 1 1 d . . . H24A H 0.7072(16) 0.2232(12) 0.1451(9) 0.040(4) 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 0.0229(5) 0.0339(6) 0.0273(5) -0.0030(4) 0.0035(4) 0.0022(4) N10 0.0243(5) 0.0410(7) 0.0299(5) 0.0017(5) 0.0024(4) -0.0019(5) C2 0.0285(6) 0.0380(8) 0.0285(6) -0.0006(6) 0.0037(5) 0.0050(6) C3 0.0289(7) 0.0468(9) 0.0322(7) -0.0011(6) 0.0080(5) 0.0006(6) C4 0.0409(8) 0.0437(9) 0.0297(7) 0.0015(6) 0.0103(6) -0.0025(7) C5 0.0409(8) 0.0356(7) 0.0249(6) 0.0009(5) 0.0037(5) 0.0035(6) C6 0.0399(8) 0.0344(7) 0.0255(6) 0.0005(5) 0.0019(5) 0.0047(6) C7 0.0346(7) 0.0403(8) 0.0277(6) -0.0031(6) -0.0047(5) 0.0041(6) C8 0.0298(7) 0.0438(9) 0.0305(7) 0.0001(6) -0.0017(5) 0.0058(6) C9 0.0256(6) 0.0390(8) 0.0311(6) 0.0025(6) 0.0006(5) 0.0017(6) C11 0.0313(7) 0.0445(8) 0.0297(7) 0.0002(6) 0.0056(5) -0.0025(6) C12 0.0238(6) 0.0571(10) 0.0348(7) 0.0000(7) 0.0048(5) 0.0044(6) C13 0.0310(7) 0.0525(9) 0.0389(8) -0.0065(7) 0.0034(6) 0.0112(7) C14 0.0342(7) 0.0391(8) 0.0270(6) -0.0027(6) 0.0067(5) 0.0049(6) C15 0.0351(7) 0.0313(7) 0.0256(6) -0.0026(5) 0.0076(5) 0.0019(6) C16 0.0303(7) 0.0340(7) 0.0305(6) -0.0063(6) 0.0032(5) -0.0023(6) C17 0.0251(6) 0.0328(7) 0.0301(6) -0.0023(5) 0.0048(5) -0.0031(5) C18 0.0249(6) 0.0319(7) 0.0284(6) -0.0027(5) 0.0047(5) -0.0017(5) C19 0.0225(6) 0.0371(8) 0.0322(6) -0.0029(6) 0.0016(5) 0.0061(5) C20 0.0341(7) 0.0332(8) 0.0407(8) -0.0060(6) 0.0076(6) 0.0040(6) C21 0.0305(6) 0.0270(7) 0.0304(6) 0.0004(5) -0.0022(5) -0.0003(5) C22 0.0294(6) 0.0325(7) 0.0305(6) 0.0049(5) -0.0020(5) -0.0010(5) C23 0.0310(7) 0.0563(10) 0.0323(7) 0.0102(7) 0.0032(6) 0.0040(7) C24 0.0247(6) 0.0516(9) 0.0391(7) 0.0109(7) 0.0059(6) -0.0031(6) _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 C19 1.4585(17) . ? N1 C2 1.4624(17) . ? N1 C18 1.4710(16) . ? N10 C24 1.4629(18) . ? N10 C9 1.4655(17) . ? N10 C11 1.4673(19) . ? C2 C3 1.5159(19) . ? C2 H2A 1.001(15) . ? C2 H2B 0.983(18) . ? C3 C4 1.534(2) . ? C3 H3A 1.002(18) . ? C3 H3B 0.987(15) . ? C4 C5 1.469(2) . ? C4 H4A 1.004(18) . ? C4 H4B 1.005(16) . ? C5 C6 1.1886(19) . ? C6 C7 1.470(2) . ? C7 C8 1.526(2) . ? C7 H7B 0.996(16) . ? C7 H7A 0.983(17) . ? C8 C9 1.5208(19) . ? C8 H8A 0.992(16) . ? C8 H8B 0.998(16) . ? C9 H9A 0.999(14) . ? C9 H9B 1.015(16) . ? C11 C12 1.514(2) . ? C11 H11A 1.016(16) . ? C11 H11B 1.003(14) . ? C12 C13 1.533(2) . ? C12 H12A 1.008(15) . ? C12 H12B 0.976(16) . ? C13 C14 1.4719(18) . ? C13 H13A 1.014(18) . ? C13 H13B 0.996(17) . ? C14 C15 1.1860(18) . ? C15 C16 1.4692(18) . ? C16 C17 1.5315(18) . ? C16 H16B 0.978(16) . ? C16 H16A 0.962(17) . ? C17 C18 1.5150(19) . ? C17 H17A 0.983(14) . ? C17 H17B 1.017(15) . ? C18 H18B 0.997(14) . ? C18 H18A 0.986(13) . ? C19 C20 1.5412(19) . ? C19 H19B 1.017(14) . ? C19 H19A 0.994(15) . ? C20 C21 1.4627(19) . ? C20 H20A 0.983(18) . ? C20 H20B 1.005(16) . ? C21 C22 1.1854(18) . ? C22 C23 1.4639(19) . ? C23 C24 1.5420(19) . ? C23 H23B 0.986(18) . ? C23 H23A 0.996(18) . ? C24 H24B 1.007(17) . ? C24 H24A 0.981(15) . ? 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 C19 N1 C2 113.72(10) . . ? C19 N1 C18 114.28(10) . . ? C2 N1 C18 110.47(10) . . ? C24 N10 C9 113.69(12) . . ? C24 N10 C11 113.94(11) . . ? C9 N10 C11 110.37(10) . . ? N1 C2 C3 114.37(11) . . ? N1 C2 H2A 110.4(9) . . ? C3 C2 H2A 108.2(9) . . ? N1 C2 H2B 107.4(9) . . ? C3 C2 H2B 109.3(9) . . ? H2A C2 H2B 106.9(12) . . ? C2 C3 C4 110.93(12) . . ? C2 C3 H3A 111.5(9) . . ? C4 C3 H3A 108.4(9) . . ? C2 C3 H3B 109.5(9) . . ? C4 C3 H3B 108.5(9) . . ? H3A C3 H3B 107.9(13) . . ? C5 C4 C3 113.64(12) . . ? C5 C4 H4A 108.6(9) . . ? C3 C4 H4A 109.0(9) . . ? C5 C4 H4B 109.1(9) . . ? C3 C4 H4B 109.5(9) . . ? H4A C4 H4B 106.8(13) . . ? C6 C5 C4 177.40(15) . . ? C5 C6 C7 178.55(15) . . ? C6 C7 C8 113.64(12) . . ? C6 C7 H7B 107.7(9) . . ? C8 C7 H7B 109.5(9) . . ? C6 C7 H7A 108.3(9) . . ? C8 C7 H7A 109.3(9) . . ? H7B C7 H7A 108.3(13) . . ? C9 C8 C7 112.18(11) . . ? C9 C8 H8A 109.4(9) . . ? C7 C8 H8A 107.5(9) . . ? C9 C8 H8B 110.6(9) . . ? C7 C8 H8B 108.4(9) . . ? H8A C8 H8B 108.5(13) . . ? N10 C9 C8 112.78(11) . . ? N10 C9 H9A 111.5(8) . . ? C8 C9 H9A 108.7(8) . . ? N10 C9 H9B 107.3(9) . . ? C8 C9 H9B 108.4(9) . . ? H9A C9 H9B 108.0(12) . . ? N10 C11 C12 114.24(12) . . ? N10 C11 H11A 107.3(9) . . ? C12 C11 H11A 107.3(9) . . ? N10 C11 H11B 110.7(8) . . ? C12 C11 H11B 108.3(8) . . ? H11A C11 H11B 108.7(12) . . ? C11 C12 C13 111.85(12) . . ? C11 C12 H12A 109.2(8) . . ? C13 C12 H12A 109.5(8) . . ? C11 C12 H12B 109.9(9) . . ? C13 C12 H12B 109.4(10) . . ? H12A C12 H12B 106.9(12) . . ? C14 C13 C12 112.60(12) . . ? C14 C13 H13A 110.2(9) . . ? C12 C13 H13A 108.4(10) . . ? C14 C13 H13B 109.0(10) . . ? C12 C13 H13B 110.2(10) . . ? H13A C13 H13B 106.2(14) . . ? C15 C14 C13 177.44(14) . . ? C14 C15 C16 178.42(15) . . ? C15 C16 C17 113.76(11) . . ? C15 C16 H16B 108.7(9) . . ? C17 C16 H16B 109.3(9) . . ? C15 C16 H16A 108.1(9) . . ? C17 C16 H16A 110.2(9) . . ? H16B C16 H16A 106.5(13) . . ? C18 C17 C16 112.01(11) . . ? C18 C17 H17A 109.1(8) . . ? C16 C17 H17A 108.8(8) . . ? C18 C17 H17B 111.2(8) . . ? C16 C17 H17B 110.2(8) . . ? H17A C17 H17B 105.3(11) . . ? N1 C18 C17 112.38(11) . . ? N1 C18 H18B 107.2(8) . . ? C17 C18 H18B 110.6(8) . . ? N1 C18 H18A 111.9(8) . . ? C17 C18 H18A 107.7(8) . . ? H18B C18 H18A 107.0(11) . . ? N1 C19 C20 118.58(11) . . ? N1 C19 H19B 107.1(8) . . ? C20 C19 H19B 109.0(8) . . ? N1 C19 H19A 108.4(9) . . ? C20 C19 H19A 106.0(8) . . ? H19B C19 H19A 107.3(11) . . ? C21 C20 C19 114.68(11) . . ? C21 C20 H20A 111.6(10) . . ? C19 C20 H20A 106.4(10) . . ? C21 C20 H20B 107.9(9) . . ? C19 C20 H20B 107.5(9) . . ? H20A C20 H20B 108.6(13) . . ? C22 C21 C20 176.39(15) . . ? C21 C22 C23 175.41(15) . . ? C22 C23 C24 115.81(12) . . ? C22 C23 H23B 108.1(10) . . ? C24 C23 H23B 110.7(10) . . ? C22 C23 H23A 108.5(10) . . ? C24 C23 H23A 106.5(10) . . ? H23B C23 H23A 106.8(13) . . ? N10 C24 C23 118.83(12) . . ? N10 C24 H24B 107.2(9) . . ? C23 C24 H24B 108.7(9) . . ? N10 C24 H24A 108.6(9) . . ? C23 C24 H24A 105.4(9) . . ? H24B C24 H24A 107.6(12) . . ? 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 C19 N1 C2 C3 58.08(16) . . . . ? C18 N1 C2 C3 -171.87(12) . . . . ? N1 C2 C3 C4 174.65(12) . . . . ? C2 C3 C4 C5 54.52(18) . . . . ? C3 C4 C5 C6 -72(3) . . . . ? C4 C5 C6 C7 -1(9) . . . . ? C5 C6 C7 C8 16(6) . . . . ? C6 C7 C8 C9 64.81(17) . . . . ? C24 N10 C9 C8 -154.64(12) . . . . ? C11 N10 C9 C8 75.90(14) . . . . ? C7 C8 C9 N10 -176.69(12) . . . . ? C24 N10 C11 C12 56.69(15) . . . . ? C9 N10 C11 C12 -173.98(11) . . . . ? N10 C11 C12 C13 -178.97(11) . . . . ? C11 C12 C13 C14 57.54(17) . . . . ? C12 C13 C14 C15 -43(4) . . . . ? C13 C14 C15 C16 -79(7) . . . . ? C14 C15 C16 C17 65(6) . . . . ? C15 C16 C17 C18 64.83(16) . . . . ? C19 N1 C18 C17 -146.53(11) . . . . ? C2 N1 C18 C17 83.72(13) . . . . ? C16 C17 C18 N1 -177.34(10) . . . . ? C2 N1 C19 C20 48.63(16) . . . . ? C18 N1 C19 C20 -79.49(14) . . . . ? N1 C19 C20 C21 51.15(18) . . . . ? C19 C20 C21 C22 -72(2) . . . . ? C20 C21 C22 C23 64(3) . . . . ? C21 C22 C23 C24 -118.3(17) . . . . ? C9 N10 C24 C23 -81.02(17) . . . . ? C11 N10 C24 C23 46.63(18) . . . . ? C22 C23 C24 N10 61.3(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.97 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.194 _refine_diff_density_min -0.180 _refine_diff_density_rms 0.040 data_768tri8 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,10-Diazabicyclo[8.8.8]hexacosa-5,14,22-triyne (47) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H36 N2' _chemical_formula_weight 352.55 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 'P 21 21 2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, -z' '-x+1/2, y+1/2, -z' _cell_length_a 12.177(2) _cell_length_b 9.875(2) _cell_length_c 8.532(1) _cell_angle_alpha 90.0 _cell_angle_beta 90.0 _cell_angle_gamma 90.0 _cell_volume 1026.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.5 _cell_measurement_theta_max 19.5 _exptl_crystal_description cube _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.141 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 388 _exptl_absorpt_coefficient_mu 0.066 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9710 _exptl_absorpt_correction_T_max 0.9837 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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_CAD4 _diffrn_measurement_method \w2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% -3 _diffrn_reflns_number 1441 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0192 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 27.95 _reflns_number_total 1441 _reflns_number_gt 1199 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0706P)^2^+0.0387P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1(4) _refine_ls_number_reflns 1441 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0498 _refine_ls_R_factor_gt 0.0348 _refine_ls_wR_factor_ref 0.0993 _refine_ls_wR_factor_gt 0.0925 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.32832(10) 0.19606(13) -0.18924(16) 0.0336(3) Uani 1 1 d . . . C2 C 0.39624(14) 0.31614(16) -0.2133(2) 0.0403(4) Uani 1 1 d . . . C3 C 0.51783(14) 0.28043(19) -0.2339(2) 0.0421(4) Uani 1 1 d . . . C4 C 0.53576(14) 0.18768(18) -0.3746(2) 0.0391(4) Uani 1 1 d . . . C5 C 0.64368(13) 0.12148(16) -0.3783(2) 0.0374(3) Uani 1 1 d . . . C6 C 0.72678(13) 0.05937(17) -0.3775(2) 0.0387(4) Uani 1 1 d . . . C7 C 0.82945(14) -0.0185(2) -0.3833(2) 0.0472(4) Uani 1 1 d . . . C8 C 0.85824(13) -0.09845(19) -0.2353(2) 0.0427(4) Uani 1 1 d . . . C9 C 0.78886(14) -0.22414(19) -0.2086(2) 0.0414(4) Uani 1 1 d . . . C10 C 0.35421(13) 0.12133(16) -0.04599(19) 0.0338(3) Uani 1 1 d . . . C11 C 0.34605(16) 0.19935(17) 0.1077(2) 0.0400(4) Uani 1 1 d . . . C12 C 0.35499(14) 0.10765(18) 0.2516(2) 0.0415(4) Uani 1 1 d . . . C13 C 0.45830(14) 0.03078(17) 0.25582(19) 0.0378(4) Uani 1 1 d . . . H2A H 0.3696(16) 0.359(2) -0.316(3) 0.051(5) Uiso 1 1 d . . . H2B H 0.3848(16) 0.385(2) -0.124(2) 0.049(5) Uiso 1 1 d . . . H3A H 0.5590(18) 0.368(3) -0.246(3) 0.063(7) Uiso 1 1 d . . . H3B H 0.5446(15) 0.2362(19) -0.137(2) 0.041(5) Uiso 1 1 d . . . H4A H 0.520(2) 0.243(3) -0.469(3) 0.070(7) Uiso 1 1 d . . . H4B H 0.4777(17) 0.122(2) -0.368(2) 0.046(5) Uiso 1 1 d . . . H7A H 0.8222(18) -0.083(2) -0.474(3) 0.056(6) Uiso 1 1 d . . . H7B H 0.8947(19) 0.044(2) -0.409(3) 0.067(7) Uiso 1 1 d . . . H8A H 0.9362(16) -0.131(2) -0.245(2) 0.047(5) Uiso 1 1 d . . . H8B H 0.8545(17) -0.0380(19) -0.142(2) 0.047(5) Uiso 1 1 d . . . H9A H 0.7946(17) -0.285(2) -0.302(3) 0.054(6) Uiso 1 1 d . . . H9B H 0.8147(17) -0.275(2) -0.117(3) 0.045(5) Uiso 1 1 d . . . H10A H 0.3029(15) 0.0429(19) -0.040(2) 0.039(5) Uiso 1 1 d . . . H10B H 0.4300(15) 0.080(2) -0.057(2) 0.041(5) Uiso 1 1 d . . . H11A H 0.4047(19) 0.266(2) 0.110(3) 0.051(6) Uiso 1 1 d . . . H11B H 0.281(2) 0.248(3) 0.111(3) 0.074(8) Uiso 1 1 d . . . H12A H 0.3463(18) 0.164(2) 0.345(3) 0.059(6) Uiso 1 1 d . . . H12B H 0.2921(17) 0.043(2) 0.254(2) 0.047(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 N1 0.0327(6) 0.0326(6) 0.0354(7) 0.0036(6) -0.0015(5) 0.0028(5) C2 0.0454(9) 0.0309(7) 0.0445(9) 0.0018(7) 0.0047(7) 0.0033(7) C3 0.0399(9) 0.0387(8) 0.0477(10) -0.0031(8) 0.0019(7) -0.0044(7) C4 0.0351(7) 0.0396(8) 0.0426(9) 0.0019(8) 0.0007(7) 0.0009(7) C5 0.0367(8) 0.0375(7) 0.0380(8) 0.0026(7) 0.0017(6) -0.0045(7) C6 0.0353(7) 0.0432(8) 0.0376(8) 0.0028(7) 0.0002(7) -0.0037(7) C7 0.0340(8) 0.0619(11) 0.0458(10) 0.0060(10) 0.0070(8) 0.0057(8) C8 0.0289(7) 0.0567(10) 0.0427(9) 0.0015(8) -0.0039(7) 0.0041(7) C9 0.0378(8) 0.0445(9) 0.0417(9) -0.0031(8) 0.0027(7) 0.0112(7) C10 0.0371(7) 0.0289(7) 0.0354(8) 0.0002(6) -0.0027(6) 0.0042(7) C11 0.0435(8) 0.0381(8) 0.0383(9) -0.0040(7) -0.0016(7) 0.0076(8) C12 0.0403(8) 0.0499(9) 0.0342(8) -0.0009(8) 0.0036(7) 0.0078(8) C13 0.0413(7) 0.0425(9) 0.0296(7) -0.0002(6) 0.0003(6) 0.0008(6) _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 C2 1.460(2) . ? N1 C10 1.462(2) . ? N1 C9 1.463(2) 2_655 ? C2 C3 1.532(2) . ? C2 H2A 1.02(2) . ? C2 H2B 1.03(2) . ? C3 C4 1.526(2) . ? C3 H3A 1.00(2) . ? C3 H3B 0.99(2) . ? C4 C5 1.468(2) . ? C4 H4A 0.99(3) . ? C4 H4B 0.96(2) . ? C5 C6 1.183(2) . ? C6 C7 1.469(2) . ? C7 C8 1.529(2) . ? C7 H7A 1.00(2) . ? C7 H7B 1.03(2) . ? C8 C9 1.519(3) . ? C8 H8A 1.01(2) . ? C8 H8B 1.00(2) . ? C9 N1 1.463(2) 2_655 ? C9 H9A 1.00(2) . ? C9 H9B 0.98(2) . ? C10 C11 1.524(2) . ? C10 H10A 0.997(19) . ? C10 H10B 1.014(19) . ? C11 C12 1.529(2) . ? C11 H11A 0.97(2) . ? C11 H11B 0.93(3) . ? C12 C13 1.470(2) . ? C12 H12A 0.98(2) . ? C12 H12B 1.00(2) . ? C13 C13 1.184(3) 2_655 ? 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 N1 C10 113.92(13) . . ? C2 N1 C9 112.50(13) . 2_655 ? C10 N1 C9 113.60(13) . 2_655 ? N1 C2 C3 112.13(13) . . ? N1 C2 H2A 106.1(11) . . ? C3 C2 H2A 107.7(11) . . ? N1 C2 H2B 111.0(11) . . ? C3 C2 H2B 111.5(11) . . ? H2A C2 H2B 108.1(15) . . ? C4 C3 C2 111.50(14) . . ? C4 C3 H3A 111.5(13) . . ? C2 C3 H3A 107.2(13) . . ? C4 C3 H3B 110.2(11) . . ? C2 C3 H3B 108.9(11) . . ? H3A C3 H3B 107.4(17) . . ? C5 C4 C3 114.33(14) . . ? C5 C4 H4A 113.4(16) . . ? C3 C4 H4A 106.4(15) . . ? C5 C4 H4B 111.0(11) . . ? C3 C4 H4B 104.7(12) . . ? H4A C4 H4B 106.2(19) . . ? C6 C5 C4 174.99(17) . . ? C5 C6 C7 177.70(19) . . ? C6 C7 C8 115.95(15) . . ? C6 C7 H7A 106.4(13) . . ? C8 C7 H7A 109.2(14) . . ? C6 C7 H7B 110.3(12) . . ? C8 C7 H7B 108.2(14) . . ? H7A C7 H7B 106.4(18) . . ? C9 C8 C7 114.72(16) . . ? C9 C8 H8A 106.1(12) . . ? C7 C8 H8A 108.1(11) . . ? C9 C8 H8B 110.2(11) . . ? C7 C8 H8B 109.8(11) . . ? H8A C8 H8B 107.6(16) . . ? N1 C9 C8 113.87(15) 2_655 . ? N1 C9 H9A 105.8(12) 2_655 . ? C8 C9 H9A 109.2(12) . . ? N1 C9 H9B 108.6(12) 2_655 . ? C8 C9 H9B 111.1(12) . . ? H9A C9 H9B 108.0(17) . . ? N1 C10 C11 116.75(13) . . ? N1 C10 H10A 107.6(11) . . ? C11 C10 H10A 107.8(11) . . ? N1 C10 H10B 108.7(12) . . ? C11 C10 H10B 110.2(11) . . ? H10A C10 H10B 105.2(15) . . ? C10 C11 C12 112.74(13) . . ? C10 C11 H11A 108.1(13) . . ? C12 C11 H11A 109.6(13) . . ? C10 C11 H11B 110.0(16) . . ? C12 C11 H11B 110.2(16) . . ? H11A C11 H11B 105.9(18) . . ? C13 C12 C11 112.75(14) . . ? C13 C12 H12A 111.5(13) . . ? C11 C12 H12A 108.0(13) . . ? C13 C12 H12B 108.9(11) . . ? C11 C12 H12B 110.1(11) . . ? H12A C12 H12B 105.3(17) . . ? C13 C13 C12 178.57(10) 2_655 . ? 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 C10 N1 C2 C3 63.22(18) . . . . ? C9 N1 C2 C3 -165.65(15) 2_655 . . . ? N1 C2 C3 C4 59.8(2) . . . . ? C2 C3 C4 C5 -165.02(15) . . . . ? C3 C4 C5 C6 103(2) . . . . ? C4 C5 C6 C7 99(5) . . . . ? C5 C6 C7 C8 -150(4) . . . . ? C6 C7 C8 C9 73.4(2) . . . . ? C7 C8 C9 N1 -61.4(2) . . . 2_655 ? C2 N1 C10 C11 57.82(18) . . . . ? C9 N1 C10 C11 -72.77(19) 2_655 . . . ? N1 C10 C11 C12 170.06(14) . . . . ? C10 C11 C12 C13 58.5(2) . . . . ? C11 C12 C13 C13 -23(10) . . . 2_655 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.95 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.138 _refine_diff_density_min -0.159 _refine_diff_density_rms 0.041 data_th2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; (48) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H68 N4' _chemical_formula_weight 629.00 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 25.4676(3) _cell_length_b 10.5968(2) _cell_length_c 14.8576(2) _cell_angle_alpha 90.00 _cell_angle_beta 93.6200(10) _cell_angle_gamma 90.00 _cell_volume 4001.70(10) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description polyhedron _exptl_crystal_colour colorless _exptl_crystal_size_max .35 _exptl_crystal_size_mid .34 _exptl_crystal_size_min .14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.044 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1392 _exptl_absorpt_coefficient_mu 0.060 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38.' _exptl_absorpt_correction_T_min 0.86 _exptl_absorpt_correction_T_max 0.97 _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14473 _diffrn_reflns_av_R_equivalents 0.0255 _diffrn_reflns_av_sigmaI/netI 0.0243 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 25.63 _reflns_number_total 3478 _reflns_number_gt 2595 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0527P)^2^+0.7679P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3478 _refine_ls_number_parameters 344 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0580 _refine_ls_R_factor_gt 0.0378 _refine_ls_wR_factor_ref 0.0992 _refine_ls_wR_factor_gt 0.0891 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.47674(7) 0.01439(17) 0.25143(11) 0.0737(5) Uani 1 1 d . . . C2 C 0.41922(9) 0.0234(3) 0.25821(13) 0.0847(6) Uani 1 1 d . . . H2A H 0.4022(8) -0.0091(19) 0.2027(15) 0.106(7) Uiso 1 1 d . . . H2B H 0.4109(8) 0.116(2) 0.2590(14) 0.111(8) Uiso 1 1 d . . . C3 C 0.39920(8) -0.04074(19) 0.34074(13) 0.0716(5) Uani 1 1 d . . . H3A H 0.3602(8) -0.0350(16) 0.3402(11) 0.082(5) Uiso 1 1 d . . . H3B H 0.4083(7) -0.1294(18) 0.3385(11) 0.082(6) Uiso 1 1 d . . . C4 C 0.42327(6) 0.01209(14) 0.42844(10) 0.0489(4) Uani 1 1 d . . . H4A H 0.4624(6) 0.0095(11) 0.4276(8) 0.039(3) Uiso 1 1 d . . . H4B H 0.4134(6) -0.0423(14) 0.4813(10) 0.060(4) Uiso 1 1 d . . . N5 N 0.40753(4) 0.14363(10) 0.44324(7) 0.0413(3) Uani 1 1 d . . . C6 C 0.44898(5) 0.21443(15) 0.49418(10) 0.0478(4) Uani 1 1 d . . . H6A H 0.4347(6) 0.2976(16) 0.5140(10) 0.067(5) Uiso 1 1 d . . . H6B H 0.4610(6) 0.1698(14) 0.5524(11) 0.062(4) Uiso 1 1 d . . . C7 C 0.49663(6) 0.24011(15) 0.44099(11) 0.0505(4) Uani 1 1 d . . . H7A H 0.5145(5) 0.1586(14) 0.4255(9) 0.056(4) Uiso 1 1 d . . . H7B H 0.4854(6) 0.2821(15) 0.3848(11) 0.067(5) Uiso 1 1 d . . . C8 C 0.47750(5) 0.49912(14) 0.25803(10) 0.0533(4) Uani 1 1 d . . . C9 C 0.42147(5) 0.49975(17) 0.27589(11) 0.0535(4) Uani 1 1 d . . . H9A H 0.4165(6) 0.5177(15) 0.3431(12) 0.072(5) Uiso 1 1 d . . . H9B H 0.4066(6) 0.4186(17) 0.2603(11) 0.071(5) Uiso 1 1 d . . . C10 C 0.39008(5) 0.59755(14) 0.22028(10) 0.0453(3) Uani 1 1 d . . . H10A H 0.3929(5) 0.5760(13) 0.1534(10) 0.050(4) Uiso 1 1 d . . . H10B H 0.4066(6) 0.6807(16) 0.2290(10) 0.064(4) Uiso 1 1 d . . . C11 C 0.33308(5) 0.60314(13) 0.24427(11) 0.0450(3) Uani 1 1 d . . . H11A H 0.3151(5) 0.6753(14) 0.2110(9) 0.049(4) Uiso 1 1 d . . . H11B H 0.3317(5) 0.6232(12) 0.3088(10) 0.049(4) Uiso 1 1 d . . . N12 N 0.30526(4) 0.48352(9) 0.22688(7) 0.0368(3) Uani 1 1 d . . . C13 C 0.28814(5) 0.47318(13) 0.13158(9) 0.0413(3) Uani 1 1 d . . . H13A H 0.2564(5) 0.5305(13) 0.1173(9) 0.048(4) Uiso 1 1 d . . . H13B H 0.3177(5) 0.5049(11) 0.0961(9) 0.040(3) Uiso 1 1 d . . . C14 C 0.27540(5) 0.33970(14) 0.10011(10) 0.0457(3) Uani 1 1 d . . . H14A H 0.2662(5) 0.3456(13) 0.0340(10) 0.054(4) Uiso 1 1 d . . . H14B H 0.2437(6) 0.3076(13) 0.1287(9) 0.053(4) Uiso 1 1 d . . . C15 C 0.32090(6) 0.24831(13) 0.11797(11) 0.0459(4) Uani 1 1 d . . . H15A H 0.3300(5) 0.2408(12) 0.1837(10) 0.047(4) Uiso 1 1 d . . . H15B H 0.3106(5) 0.1633(15) 0.0953(9) 0.054(4) Uiso 1 1 d . . . C16 C 0.36937(6) 0.28308(12) 0.07545(10) 0.0465(4) Uani 1 1 d . . . C17 C 0.40988(6) 0.30629(13) 0.04283(11) 0.0523(4) Uani 1 1 d . . . C18 C 0.46175(6) 0.31935(17) 0.00612(14) 0.0630(5) Uani 1 1 d . . . H18A H 0.4718(7) 0.4053(17) 0.0051(11) 0.081(5) Uiso 1 1 d . . . H18B H 0.4607(7) 0.2938(17) -0.0607(14) 0.091(6) Uiso 1 1 d . . . C19 C 0.35827(5) 0.14657(15) 0.48931(10) 0.0470(4) Uani 1 1 d . . . H19A H 0.3361(5) 0.0774(13) 0.4619(9) 0.048(4) Uiso 1 1 d . . . H19B H 0.3654(5) 0.1220(13) 0.5536(10) 0.057(4) Uiso 1 1 d . . . C20 C 0.32936(6) 0.27145(15) 0.48176(9) 0.0457(4) Uani 1 1 d . . . H20A H 0.3532(5) 0.3395(14) 0.5065(9) 0.051(4) Uiso 1 1 d . . . H20B H 0.3001(5) 0.2676(12) 0.5201(9) 0.047(4) Uiso 1 1 d . . . C21 C 0.30938(5) 0.30583(13) 0.38674(9) 0.0415(3) Uani 1 1 d . . . H21A H 0.3397(5) 0.3093(11) 0.3486(8) 0.038(3) Uiso 1 1 d . . . H21B H 0.2872(6) 0.2390(14) 0.3617(9) 0.053(4) Uiso 1 1 d . . . C22 C 0.28002(6) 0.43089(14) 0.38099(10) 0.0465(4) Uani 1 1 d . . . H22A H 0.2504(6) 0.4255(13) 0.4172(9) 0.052(4) Uiso 1 1 d . . . H22B H 0.3034(5) 0.4998(13) 0.4102(9) 0.050(4) Uiso 1 1 d . . . C23 C 0.26152(5) 0.46750(15) 0.28554(9) 0.0452(3) Uani 1 1 d . . . H23A H 0.2408(5) 0.5463(14) 0.2860(9) 0.048(4) Uiso 1 1 d . . . H23B H 0.2389(6) 0.3975(14) 0.2578(9) 0.053(4) 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 0.0979(15) 0.0785(12) 0.0441(9) -0.0023(9) -0.0013(11) 0.0076(9) C2 0.0902(15) 0.1087(18) 0.0530(11) -0.0141(11) -0.0132(10) 0.0227(13) C3 0.0604(12) 0.0688(12) 0.0843(14) -0.0214(10) -0.0065(10) 0.0026(9) C4 0.0463(9) 0.0439(8) 0.0563(9) 0.0072(7) 0.0016(7) 0.0028(7) N5 0.0357(6) 0.0438(6) 0.0448(6) 0.0049(5) 0.0045(5) 0.0025(5) C6 0.0408(8) 0.0500(9) 0.0530(9) -0.0024(7) 0.0054(7) 0.0026(7) C7 0.0406(8) 0.0526(9) 0.0584(10) 0.0062(8) 0.0046(7) 0.0010(7) C8 0.0425(7) 0.0556(9) 0.0602(9) 0.0017(7) -0.0091(7) -0.0016(6) C9 0.0357(8) 0.0632(10) 0.0606(10) 0.0057(8) -0.0051(7) -0.0035(7) C10 0.0413(8) 0.0397(8) 0.0545(9) -0.0019(7) 0.0008(6) -0.0040(6) C11 0.0439(8) 0.0386(8) 0.0526(9) -0.0057(7) 0.0025(7) 0.0045(6) N12 0.0326(6) 0.0379(6) 0.0402(6) -0.0019(5) 0.0035(5) 0.0019(4) C13 0.0362(7) 0.0437(8) 0.0437(7) 0.0026(6) -0.0006(6) 0.0060(6) C14 0.0387(8) 0.0516(9) 0.0466(8) -0.0048(7) 0.0006(6) -0.0036(6) C15 0.0475(9) 0.0391(8) 0.0511(9) -0.0045(7) 0.0044(7) -0.0027(6) C16 0.0457(9) 0.0364(7) 0.0572(9) -0.0067(6) 0.0017(7) 0.0035(6) C17 0.0463(9) 0.0387(8) 0.0718(10) -0.0001(7) 0.0046(8) 0.0043(6) C18 0.0466(9) 0.0508(10) 0.0930(14) 0.0153(9) 0.0150(9) 0.0033(7) C19 0.0408(8) 0.0585(9) 0.0419(8) 0.0103(7) 0.0054(6) -0.0012(7) C20 0.0360(8) 0.0620(10) 0.0400(8) -0.0002(7) 0.0098(6) 0.0032(7) C21 0.0383(8) 0.0457(8) 0.0409(8) -0.0020(6) 0.0061(6) -0.0001(6) C22 0.0428(8) 0.0533(9) 0.0445(8) -0.0011(7) 0.0123(7) 0.0068(7) C23 0.0347(7) 0.0506(9) 0.0510(8) 0.0005(7) 0.0075(6) 0.0099(7) _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 C1 1.188(4) 2_655 ? C1 C2 1.478(3) . ? C2 C3 1.518(3) . ? C3 C4 1.512(2) . ? C4 N5 1.4708(18) . ? N5 C6 1.4660(18) . ? N5 C19 1.4668(16) . ? C6 C7 1.5139(19) . ? C7 C18 1.530(2) 2_655 ? C8 C8 1.185(3) 2_655 ? C8 C9 1.468(2) . ? C9 C10 1.521(2) . ? C10 C11 1.5176(19) . ? C11 N12 1.4671(16) . ? N12 C13 1.4591(16) . ? N12 C23 1.4670(16) . ? C13 C14 1.5184(19) . ? C14 C15 1.521(2) . ? C15 C16 1.469(2) . ? C16 C17 1.1928(18) . ? C17 C18 1.467(2) . ? C18 C7 1.530(2) 2_655 ? C19 C20 1.515(2) . ? C20 C21 1.5145(19) . ? C21 C22 1.5213(19) . ? C22 C23 1.5164(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 C1 C1 C2 175.84(16) 2_655 . ? C1 C2 C3 114.26(17) . . ? C4 C3 C2 113.05(17) . . ? N5 C4 C3 112.35(13) . . ? C6 N5 C19 110.95(11) . . ? C6 N5 C4 111.59(11) . . ? C19 N5 C4 109.82(11) . . ? N5 C6 C7 113.41(12) . . ? C6 C7 C18 112.50(13) . 2_655 ? C8 C8 C9 178.8(2) 2_655 . ? C8 C9 C10 112.86(13) . . ? C11 C10 C9 112.13(12) . . ? N12 C11 C10 112.55(11) . . ? C13 N12 C23 112.10(10) . . ? C13 N12 C11 110.31(10) . . ? C23 N12 C11 111.83(10) . . ? N12 C13 C14 114.44(11) . . ? C13 C14 C15 113.19(11) . . ? C16 C15 C14 114.65(12) . . ? C17 C16 C15 176.82(15) . . ? C16 C17 C18 173.02(15) . . ? C17 C18 C7 111.60(14) . 2_655 ? N5 C19 C20 114.20(11) . . ? C21 C20 C19 114.35(12) . . ? C20 C21 C22 113.38(12) . . ? C23 C22 C21 113.45(12) . . ? N12 C23 C22 112.48(11) . . ? _diffrn_measured_fraction_theta_max 0.920 _diffrn_reflns_theta_full 25.63 _diffrn_measured_fraction_theta_full 0.920 _refine_diff_density_max 0.167 _refine_diff_density_min -0.131 _refine_diff_density_rms 0.029