# Electronic Supplementary Material (ESI) for Soft Matter # This journal is © The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 777 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Lloyd, Gareth' 'Piepenbrock, Marc-Oliver' 'Foster, Jonathan' 'Clarke, Nigel' 'Steed, Jonathan' _publ_contact_author_name 'Dr Jonathan Steed' _publ_contact_author_email jon.steed@durham.ac.uk _publ_section_title ; ; # Attachment 'n=4.cif' data_z:\xraydata\marc\07srv299\work\xm _database_code_depnum_ccdc_archive 'CCDC 681966' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H30 N4 O2' _chemical_formula_sum 'C22 H30 N4 O2' _chemical_formula_weight 382.50 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' 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 C2 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 35.285(15) _cell_length_b 4.651(2) _cell_length_c 12.784(5) _cell_angle_alpha 90.00 _cell_angle_beta 97.518(7) _cell_angle_gamma 90.00 _cell_volume 2079.7(15) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 1015 _cell_measurement_theta_min 3.215 _cell_measurement_theta_max 27.866 _exptl_crystal_description needles _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.222 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 0.080 _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 120(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 1K _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12725 _diffrn_reflns_av_R_equivalents 0.0619 _diffrn_reflns_av_sigmaI/netI 0.0615 _diffrn_reflns_limit_h_min -46 _diffrn_reflns_limit_h_max 46 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.16 _diffrn_reflns_theta_max 28.20 _reflns_number_total 5076 _reflns_number_gt 4339 _reflns_threshold_expression >2sigma(I) _computing_data_collection Smart _computing_cell_refinement Saint _computing_data_reduction Saint _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Xseed _computing_publication_material Xseed _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^)+(0.0719P)^2^+5.7739P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 2(2) _refine_ls_number_reflns 5076 _refine_ls_number_parameters 253 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0888 _refine_ls_R_factor_gt 0.0762 _refine_ls_wR_factor_ref 0.2024 _refine_ls_wR_factor_gt 0.1960 _refine_ls_goodness_of_fit_ref 1.157 _refine_ls_restrained_S_all 1.157 _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 O1 O 0.43376(7) 0.2562(5) 0.6444(2) 0.0205(5) Uani 1 1 d . . . N2 N 0.40208(8) -0.1645(6) 0.6087(2) 0.0196(6) Uani 1 1 d . . . H2 H 0.4020 -0.3524 0.6170 0.024 Uiso 1 1 calc R . . N3 N 0.18352(8) -0.1728(6) 0.2364(2) 0.0190(6) Uani 1 1 d . . . H3 H 0.1801 0.0056 0.2561 0.023 Uiso 1 1 calc R . . N4 N 0.24135(8) -0.1715(6) 0.3425(2) 0.0186(6) Uani 1 1 d . . . H4 H 0.2379 0.0129 0.3535 0.022 Uiso 1 1 calc R . . O5 O 0.21587(7) -0.5937(5) 0.2765(2) 0.0217(5) Uani 1 1 d . . . C6 C 0.43338(9) -0.0113(7) 0.6483(3) 0.0164(6) Uani 1 1 d . . . C7 C 0.34003(9) -0.2437(7) 0.5025(3) 0.0188(7) Uani 1 1 d . . . H7A H 0.3328 -0.3753 0.5576 0.023 Uiso 1 1 calc R . . H7B H 0.3519 -0.3596 0.4506 0.023 Uiso 1 1 calc R . . N8 N 0.46394(8) -0.1695(6) 0.6898(2) 0.0225(6) Uani 1 1 d . . . H8 H 0.4630 -0.3579 0.6833 0.027 Uiso 1 1 calc R . . C9 C 0.36869(9) -0.0235(8) 0.5528(3) 0.0208(7) Uani 1 1 d . . . H9A H 0.3766 0.1033 0.4974 0.025 Uiso 1 1 calc R . . H9B H 0.3565 0.0974 0.6027 0.025 Uiso 1 1 calc R . . C10 C 0.11847(10) -0.1397(9) 0.1443(3) 0.0233(7) Uani 1 1 d . . . H10A H 0.1096 -0.1303 0.2137 0.035 Uiso 1 1 calc R . . H10B H 0.0994 -0.2402 0.0948 0.035 Uiso 1 1 calc R . . H10C H 0.1221 0.0556 0.1186 0.035 Uiso 1 1 calc R . . C11 C 0.27657(9) -0.3107(7) 0.3882(3) 0.0194(7) Uani 1 1 d . . . H11A H 0.2889 -0.4023 0.3315 0.023 Uiso 1 1 calc R . . H11B H 0.2706 -0.4632 0.4376 0.023 Uiso 1 1 calc R . . C12 C 0.21373(9) -0.3246(7) 0.2830(2) 0.0161(6) Uani 1 1 d . . . C13 C 0.49873(10) -0.0351(8) 0.7455(3) 0.0213(7) Uani 1 1 d . . . H13 H 0.5035 0.1470 0.7077 0.026 Uiso 1 1 calc R . . C14 C 0.30406(10) -0.0945(7) 0.4471(3) 0.0185(7) Uani 1 1 d . . . H14A H 0.2910 0.0077 0.5002 0.022 Uiso 1 1 calc R . . H14B H 0.3115 0.0497 0.3967 0.022 Uiso 1 1 calc R . . C15 C 0.20261(10) -0.1495(9) 0.0253(3) 0.0249(8) Uani 1 1 d . . . H15 H 0.2145 -0.0206 0.0772 0.030 Uiso 1 1 calc R . . C16 C 0.53213(9) -0.2361(8) 0.7371(3) 0.0213(7) Uani 1 1 d . . . C17 C 0.15636(9) -0.3021(7) 0.1533(3) 0.0173(7) Uani 1 1 d . . . H17 H 0.1514 -0.5037 0.1753 0.021 Uiso 1 1 calc R . . C18 C 0.17202(10) -0.3168(7) 0.0478(3) 0.0199(7) Uani 1 1 d . . . C19 C 0.53877(10) -0.3250(9) 0.6370(3) 0.0272(8) Uani 1 1 d . . . H19 H 0.5229 -0.2544 0.5767 0.033 Uiso 1 1 calc R . . C20 C 0.59204(11) -0.6142(9) 0.7119(3) 0.0311(9) Uani 1 1 d . . . H20 H 0.6122 -0.7446 0.7039 0.037 Uiso 1 1 calc R . . C21 C 0.19908(12) -0.3546(9) -0.1483(3) 0.0315(9) Uani 1 1 d . . . H21 H 0.2085 -0.3694 -0.2143 0.038 Uiso 1 1 calc R . . C22 C 0.16834(12) -0.5197(9) -0.1278(3) 0.0311(9) Uani 1 1 d . . . H22 H 0.1563 -0.6449 -0.1808 0.037 Uiso 1 1 calc R . . C23 C 0.56830(11) -0.5160(10) 0.6236(3) 0.0309(9) Uani 1 1 d . . . H23 H 0.5721 -0.5781 0.5550 0.037 Uiso 1 1 calc R . . C24 C 0.21597(12) -0.1688(10) -0.0724(3) 0.0308(9) Uani 1 1 d . . . H24 H 0.2369 -0.0529 -0.0867 0.037 Uiso 1 1 calc R . . C25 C 0.15488(10) -0.5045(8) -0.0311(3) 0.0240(7) Uani 1 1 d . . . H25 H 0.1339 -0.6214 -0.0178 0.029 Uiso 1 1 calc R . . C26 C 0.55622(11) -0.3369(9) 0.8240(3) 0.0266(8) Uani 1 1 d . . . H26 H 0.5522 -0.2791 0.8929 0.032 Uiso 1 1 calc R . . C27 C 0.58624(11) -0.5217(9) 0.8110(3) 0.0318(9) Uani 1 1 d . . . H27 H 0.6029 -0.5849 0.8709 0.038 Uiso 1 1 calc R . . C28 C 0.49248(11) 0.0439(10) 0.8585(3) 0.0307(9) Uani 1 1 d . . . H28A H 0.4706 0.1741 0.8565 0.046 Uiso 1 1 calc R . . H28B H 0.5154 0.1392 0.8941 0.046 Uiso 1 1 calc R . . H28C H 0.4875 -0.1311 0.8972 0.046 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 O1 0.0180(11) 0.0129(12) 0.0293(13) 0.0001(10) -0.0020(10) 0.0006(9) N2 0.0199(14) 0.0102(13) 0.0267(15) 0.0014(11) -0.0042(11) 0.0011(11) N3 0.0208(14) 0.0127(14) 0.0217(14) -0.0027(11) -0.0045(11) -0.0014(11) N4 0.0195(13) 0.0124(14) 0.0228(14) 0.0003(11) -0.0014(11) 0.0031(11) O5 0.0249(13) 0.0104(11) 0.0280(13) 0.0000(9) -0.0033(10) -0.0010(9) C6 0.0180(15) 0.0136(15) 0.0178(15) 0.0013(12) 0.0027(12) 0.0018(12) C7 0.0177(15) 0.0126(14) 0.0246(17) 0.0015(13) -0.0026(12) 0.0013(12) N8 0.0194(14) 0.0113(14) 0.0341(17) 0.0009(12) -0.0064(12) 0.0000(11) C9 0.0141(15) 0.0177(17) 0.0291(18) 0.0009(14) -0.0026(13) -0.0005(13) C10 0.0167(15) 0.031(2) 0.0220(16) 0.0008(15) 0.0024(12) 0.0002(14) C11 0.0179(15) 0.0138(16) 0.0248(17) -0.0033(13) -0.0032(13) 0.0009(13) C12 0.0214(16) 0.0126(15) 0.0145(15) 0.0022(12) 0.0033(12) -0.0007(12) C13 0.0179(15) 0.0199(17) 0.0248(17) -0.0006(14) -0.0023(13) -0.0021(13) C14 0.0202(15) 0.0134(15) 0.0204(16) -0.0009(13) -0.0033(12) 0.0032(13) C15 0.0216(17) 0.0264(19) 0.0265(18) -0.0002(15) 0.0030(14) -0.0023(15) C16 0.0161(15) 0.0193(16) 0.0273(18) -0.0013(14) -0.0020(13) -0.0052(13) C17 0.0175(15) 0.0128(15) 0.0201(15) -0.0001(13) -0.0037(12) -0.0042(12) C18 0.0203(16) 0.0166(16) 0.0211(16) 0.0021(13) -0.0033(13) 0.0036(13) C19 0.0229(17) 0.032(2) 0.0256(18) 0.0092(16) -0.0005(14) 0.0031(16) C20 0.0245(18) 0.025(2) 0.043(2) 0.0015(17) -0.0001(16) 0.0072(16) C21 0.036(2) 0.033(2) 0.0259(19) 0.0008(17) 0.0075(16) 0.0124(18) C22 0.042(2) 0.024(2) 0.0253(19) -0.0040(16) -0.0042(16) 0.0074(17) C23 0.0300(19) 0.036(2) 0.028(2) 0.0011(17) 0.0099(15) 0.0044(18) C24 0.0291(19) 0.034(2) 0.030(2) 0.0031(17) 0.0081(16) 0.0067(17) C25 0.0258(17) 0.0211(18) 0.0242(17) -0.0034(14) -0.0002(14) -0.0007(14) C26 0.0273(18) 0.0266(19) 0.0245(18) 0.0005(16) -0.0023(14) -0.0003(16) C27 0.0258(19) 0.031(2) 0.036(2) 0.0021(18) -0.0048(16) 0.0066(17) C28 0.0290(18) 0.034(2) 0.029(2) -0.0066(17) 0.0018(15) 0.0049(17) _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 O1 C6 1.245(4) . ? N2 C6 1.355(4) . ? N2 C9 1.452(4) . ? N2 H2 0.8800 . ? N3 C12 1.351(4) . ? N3 C17 1.463(4) . ? N3 H3 0.8800 . ? N4 C12 1.357(4) . ? N4 C11 1.454(4) . ? N4 H4 0.8800 . ? O5 C12 1.257(4) . ? C6 N8 1.355(4) . ? C7 C9 1.521(5) . ? C7 C14 1.536(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? N8 C13 1.475(4) . ? N8 H8 0.8800 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C17 1.527(5) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C14 1.526(5) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C13 C16 1.519(5) . ? C13 C28 1.535(5) . ? C13 H13 1.0000 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C18 1.391(5) . ? C15 C24 1.395(5) . ? C15 H15 0.9500 . ? C16 C26 1.389(5) . ? C16 C19 1.393(5) . ? C17 C18 1.525(5) . ? C17 H17 1.0000 . ? C18 C25 1.409(5) . ? C19 C23 1.396(6) . ? C19 H19 0.9500 . ? C20 C27 1.378(6) . ? C20 C23 1.391(6) . ? C20 H20 0.9500 . ? C21 C24 1.375(6) . ? C21 C22 1.381(6) . ? C21 H21 0.9500 . ? C22 C25 1.383(5) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? C26 C27 1.391(6) . ? C26 H26 0.9500 . ? C27 H27 0.9500 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 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 C6 N2 C9 121.0(3) . . ? C6 N2 H2 119.5 . . ? C9 N2 H2 119.5 . . ? C12 N3 C17 120.6(3) . . ? C12 N3 H3 119.7 . . ? C17 N3 H3 119.7 . . ? C12 N4 C11 120.3(3) . . ? C12 N4 H4 119.8 . . ? C11 N4 H4 119.8 . . ? O1 C6 N8 123.1(3) . . ? O1 C6 N2 121.5(3) . . ? N8 C6 N2 115.4(3) . . ? C9 C7 C14 110.8(3) . . ? C9 C7 H7A 109.5 . . ? C14 C7 H7A 109.5 . . ? C9 C7 H7B 109.5 . . ? C14 C7 H7B 109.5 . . ? H7A C7 H7B 108.1 . . ? C6 N8 C13 121.9(3) . . ? C6 N8 H8 119.1 . . ? C13 N8 H8 119.1 . . ? N2 C9 C7 110.8(3) . . ? N2 C9 H9A 109.5 . . ? C7 C9 H9A 109.5 . . ? N2 C9 H9B 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 108.1 . . ? C17 C10 H10A 109.5 . . ? C17 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C17 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N4 C11 C14 111.1(3) . . ? N4 C11 H11A 109.4 . . ? C14 C11 H11A 109.4 . . ? N4 C11 H11B 109.4 . . ? C14 C11 H11B 109.4 . . ? H11A C11 H11B 108.0 . . ? O5 C12 N3 122.8(3) . . ? O5 C12 N4 121.0(3) . . ? N3 C12 N4 116.2(3) . . ? N8 C13 C16 108.0(3) . . ? N8 C13 C28 110.1(3) . . ? C16 C13 C28 115.0(3) . . ? N8 C13 H13 107.8 . . ? C16 C13 H13 107.8 . . ? C28 C13 H13 107.8 . . ? C11 C14 C7 111.3(3) . . ? C11 C14 H14A 109.4 . . ? C7 C14 H14A 109.4 . . ? C11 C14 H14B 109.4 . . ? C7 C14 H14B 109.4 . . ? H14A C14 H14B 108.0 . . ? C18 C15 C24 120.8(4) . . ? C18 C15 H15 119.6 . . ? C24 C15 H15 119.6 . . ? C26 C16 C19 118.4(3) . . ? C26 C16 C13 123.4(3) . . ? C19 C16 C13 118.2(3) . . ? N3 C17 C10 109.6(3) . . ? N3 C17 C18 112.4(3) . . ? C10 C17 C18 111.7(3) . . ? N3 C17 H17 107.6 . . ? C10 C17 H17 107.6 . . ? C18 C17 H17 107.6 . . ? C15 C18 C25 118.1(3) . . ? C15 C18 C17 122.6(3) . . ? C25 C18 C17 119.3(3) . . ? C23 C19 C16 121.3(3) . . ? C23 C19 H19 119.4 . . ? C16 C19 H19 119.4 . . ? C27 C20 C23 119.8(4) . . ? C27 C20 H20 120.1 . . ? C23 C20 H20 120.1 . . ? C24 C21 C22 119.6(4) . . ? C24 C21 H21 120.2 . . ? C22 C21 H21 120.2 . . ? C21 C22 C25 120.7(4) . . ? C21 C22 H22 119.6 . . ? C25 C22 H22 119.6 . . ? C20 C23 C19 119.3(4) . . ? C20 C23 H23 120.4 . . ? C19 C23 H23 120.4 . . ? C21 C24 C15 120.4(4) . . ? C21 C24 H24 119.8 . . ? C15 C24 H24 119.8 . . ? C22 C25 C18 120.4(4) . . ? C22 C25 H25 119.8 . . ? C18 C25 H25 119.8 . . ? C27 C26 C16 120.6(4) . . ? C27 C26 H26 119.7 . . ? C16 C26 H26 119.7 . . ? C20 C27 C26 120.7(4) . . ? C20 C27 H27 119.7 . . ? C26 C27 H27 119.7 . . ? C13 C28 H28A 109.5 . . ? C13 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C13 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? 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 C9 N2 C6 O1 4.8(5) . . . . ? C9 N2 C6 N8 -174.0(3) . . . . ? O1 C6 N8 C13 7.5(5) . . . . ? N2 C6 N8 C13 -173.7(3) . . . . ? C6 N2 C9 C7 171.6(3) . . . . ? C14 C7 C9 N2 177.8(3) . . . . ? C12 N4 C11 C14 177.2(3) . . . . ? C17 N3 C12 O5 -16.3(5) . . . . ? C17 N3 C12 N4 166.8(3) . . . . ? C11 N4 C12 O5 8.6(5) . . . . ? C11 N4 C12 N3 -174.5(3) . . . . ? C6 N8 C13 C16 -154.4(3) . . . . ? C6 N8 C13 C28 79.3(4) . . . . ? N4 C11 C14 C7 175.7(3) . . . . ? C9 C7 C14 C11 175.1(3) . . . . ? N8 C13 C16 C26 -125.1(4) . . . . ? C28 C13 C16 C26 -1.8(5) . . . . ? N8 C13 C16 C19 54.5(4) . . . . ? C28 C13 C16 C19 177.9(3) . . . . ? C12 N3 C17 C10 158.4(3) . . . . ? C12 N3 C17 C18 -76.7(4) . . . . ? C24 C15 C18 C25 -0.3(5) . . . . ? C24 C15 C18 C17 -179.8(3) . . . . ? N3 C17 C18 C15 -18.6(5) . . . . ? C10 C17 C18 C15 105.1(4) . . . . ? N3 C17 C18 C25 161.9(3) . . . . ? C10 C17 C18 C25 -74.3(4) . . . . ? C26 C16 C19 C23 1.5(6) . . . . ? C13 C16 C19 C23 -178.2(4) . . . . ? C24 C21 C22 C25 -1.4(6) . . . . ? C27 C20 C23 C19 -0.2(6) . . . . ? C16 C19 C23 C20 -1.4(6) . . . . ? C22 C21 C24 C15 1.0(6) . . . . ? C18 C15 C24 C21 -0.1(6) . . . . ? C21 C22 C25 C18 0.9(6) . . . . ? C15 C18 C25 C22 -0.1(5) . . . . ? C17 C18 C25 C22 179.4(3) . . . . ? C19 C16 C26 C27 0.1(6) . . . . ? C13 C16 C26 C27 179.7(4) . . . . ? C23 C20 C27 C26 1.7(6) . . . . ? C16 C26 C27 C20 -1.7(6) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.396 _refine_diff_density_min -0.367 _refine_diff_density_rms 0.075 # Attachment 'n=5.cif' data_z:\xraydata\marc\07srv400\work\xm _database_code_depnum_ccdc_archive 'CCDC 681967' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H32 N4 O2' _chemical_formula_sum 'C23 H32 N4 O2' _chemical_formula_weight 396.53 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 P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 12.317(2) _cell_length_b 4.6108(8) _cell_length_c 19.488(3) _cell_angle_alpha 90.00 _cell_angle_beta 107.519(4) _cell_angle_gamma 90.00 _cell_volume 1055.4(3) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 861 _cell_measurement_theta_min 2.193 _cell_measurement_theta_max 27.657 _exptl_crystal_description 'flat needles' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.248 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 428 _exptl_absorpt_coefficient_mu 0.081 _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 120(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 Smart-6k _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7923 _diffrn_reflns_av_R_equivalents 0.0499 _diffrn_reflns_av_sigmaI/netI 0.0867 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.10 _diffrn_reflns_theta_max 27.54 _reflns_number_total 4625 _reflns_number_gt 3061 _reflns_threshold_expression >2sigma(I) _computing_data_collection Smart _computing_cell_refinement Saint _computing_data_reduction Saint _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Xseed _computing_publication_material Xseed _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^)+(0.0809P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -2(2) _refine_ls_number_reflns 4625 _refine_ls_number_parameters 262 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1040 _refine_ls_R_factor_gt 0.0624 _refine_ls_wR_factor_ref 0.1628 _refine_ls_wR_factor_gt 0.1354 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.017 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 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 0.4436(2) 0.4873(6) 0.38654(13) 0.0187(6) Uani 1 1 d . . . H1 H 0.4433 0.2966 0.3845 0.022 Uiso 1 1 calc R . . C2 C 0.1248(2) 0.6393(7) 0.58019(17) 0.0197(7) Uani 1 1 d . . . H2A H 0.1864 0.7335 0.6185 0.024 Uiso 1 1 calc R . . H2B H 0.0814 0.7936 0.5482 0.024 Uiso 1 1 calc R . . C3 C 0.3925(2) 0.6312(7) 0.43544(16) 0.0170(7) Uani 1 1 d . . . H3A H 0.3520 0.8067 0.4117 0.020 Uiso 1 1 calc R . . H3B H 0.4537 0.6944 0.4787 0.020 Uiso 1 1 calc R . . N4 N -0.0653(2) 0.4734(6) 0.68713(14) 0.0214(6) Uani 1 1 d . . . H4 H -0.0831 0.2932 0.6734 0.026 Uiso 1 1 calc R . . O5 O 0.00473(19) 0.9024(5) 0.65992(12) 0.0245(5) Uani 1 1 d . . . O6 O 0.49192(18) 0.9115(5) 0.34418(11) 0.0217(5) Uani 1 1 d . . . C7 C -0.0030(2) 0.6349(7) 0.65423(17) 0.0188(7) Uani 1 1 d . . . C8 C 0.2539(2) 0.6163(7) 0.50483(16) 0.0182(7) Uani 1 1 d . . . H8A H 0.2084 0.7734 0.4750 0.022 Uiso 1 1 calc R . . H8B H 0.3142 0.7084 0.5443 0.022 Uiso 1 1 calc R . . C9 C 0.4913(2) 0.6404(7) 0.34424(16) 0.0175(7) Uani 1 1 d . . . N10 N 0.5365(2) 0.4829(6) 0.30144(14) 0.0199(6) Uani 1 1 d . . . H10 H 0.5518 0.2986 0.3115 0.024 Uiso 1 1 calc R . . N11 N 0.0484(2) 0.4856(6) 0.61332(14) 0.0198(6) Uani 1 1 d . . . H11 H 0.0365 0.2982 0.6065 0.024 Uiso 1 1 calc R . . C12 C 0.1769(2) 0.4409(8) 0.53734(16) 0.0181(7) Uani 1 1 d . . . H12A H 0.1160 0.3466 0.4986 0.022 Uiso 1 1 calc R . . H12B H 0.2216 0.2875 0.5690 0.022 Uiso 1 1 calc R . . C13 C -0.1028(2) 0.5966(8) 0.74496(17) 0.0202(7) Uani 1 1 d . . . H13 H -0.1256 0.8024 0.7321 0.024 Uiso 1 1 calc R . . C14 C 0.5107(2) 0.4134(8) 0.17473(16) 0.0193(6) Uani 1 1 d . . . C15 C 0.5611(2) 0.6090(8) 0.23847(16) 0.0199(7) Uani 1 1 d . . . H15 H 0.5200 0.7985 0.2280 0.024 Uiso 1 1 calc R . . C16 C -0.2084(2) 0.4317(9) 0.74975(18) 0.0249(7) Uani 1 1 d . . . H16A H -0.2669 0.4348 0.7027 0.037 Uiso 1 1 calc R . . H16B H -0.2382 0.5245 0.7856 0.037 Uiso 1 1 calc R . . H16C H -0.1878 0.2304 0.7640 0.037 Uiso 1 1 calc R . . C17 C 0.3432(3) 0.1786(8) 0.09752(19) 0.0298(8) Uani 1 1 d . . . H17 H 0.2635 0.1443 0.0847 0.036 Uiso 1 1 calc R . . C18 C 0.5229(3) 0.1050(8) 0.07739(18) 0.0277(7) Uani 1 1 d . . . H18 H 0.5679 0.0182 0.0510 0.033 Uiso 1 1 calc R . . C19 C 0.3099(2) 0.4410(8) 0.45877(16) 0.0186(7) Uani 1 1 d . . . H19A H 0.3509 0.2737 0.4866 0.022 Uiso 1 1 calc R . . H19B H 0.2510 0.3657 0.4159 0.022 Uiso 1 1 calc R . . C20 C 0.6881(2) 0.6730(8) 0.25421(18) 0.0251(8) Uani 1 1 d . . . H20A H 0.7135 0.8004 0.2963 0.038 Uiso 1 1 calc R . . H20B H 0.7011 0.7689 0.2125 0.038 Uiso 1 1 calc R . . H20C H 0.7310 0.4910 0.2640 0.038 Uiso 1 1 calc R . . C21 C 0.5738(2) 0.2853(8) 0.13447(17) 0.0215(7) Uani 1 1 d . . . H21 H 0.6532 0.3227 0.1465 0.026 Uiso 1 1 calc R . . C22 C -0.0235(3) 0.7657(9) 0.87278(19) 0.0316(8) Uani 1 1 d . . . H22 H -0.0888 0.8858 0.8645 0.038 Uiso 1 1 calc R . . C23 C 0.4067(3) 0.0485(8) 0.05790(18) 0.0278(8) Uani 1 1 d . . . H23 H 0.3717 -0.0757 0.0186 0.033 Uiso 1 1 calc R . . C24 C -0.0113(3) 0.5970(8) 0.81701(18) 0.0242(7) Uani 1 1 d . . . C25 C 0.1505(3) 0.5886(11) 0.9524(2) 0.0424(11) Uani 1 1 d . . . H25 H 0.2053 0.5843 0.9987 0.051 Uiso 1 1 calc R . . C26 C 0.3930(3) 0.3537(8) 0.15423(18) 0.0253(8) Uani 1 1 d . . . H26 H 0.3476 0.4378 0.1807 0.030 Uiso 1 1 calc R . . C27 C 0.0856(3) 0.4226(9) 0.8307(2) 0.0336(9) Uani 1 1 d . . . H27 H 0.0972 0.3047 0.7936 0.040 Uiso 1 1 calc R . . C28 C 0.0550(4) 0.7658(10) 0.9393(2) 0.0417(10) Uani 1 1 d . . . H28 H 0.0446 0.8860 0.9764 0.050 Uiso 1 1 calc R . . C29 C 0.1643(3) 0.4212(11) 0.8980(2) 0.0414(10) Uani 1 1 d . . . H29 H 0.2296 0.3010 0.9067 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 0.0194(13) 0.0137(14) 0.0286(14) 0.0000(11) 0.0156(11) 0.0001(11) C2 0.0160(14) 0.0205(18) 0.0286(16) 0.0013(15) 0.0159(13) -0.0024(14) C3 0.0142(14) 0.0144(17) 0.0265(16) -0.0018(14) 0.0125(12) -0.0022(12) N4 0.0180(13) 0.0184(15) 0.0343(15) 0.0001(13) 0.0178(11) 0.0007(12) O5 0.0240(12) 0.0166(12) 0.0404(14) -0.0024(11) 0.0212(10) -0.0009(10) O6 0.0213(11) 0.0140(11) 0.0358(13) 0.0005(11) 0.0178(10) -0.0008(9) C7 0.0123(14) 0.0188(18) 0.0271(16) -0.0018(14) 0.0087(13) -0.0027(13) C8 0.0142(13) 0.0187(16) 0.0267(16) -0.0003(15) 0.0138(12) -0.0002(14) C9 0.0098(13) 0.0197(18) 0.0242(16) -0.0012(14) 0.0070(12) -0.0014(13) N10 0.0216(13) 0.0170(14) 0.0269(14) 0.0027(11) 0.0160(11) 0.0015(12) N11 0.0163(12) 0.0152(14) 0.0342(15) -0.0001(11) 0.0172(11) -0.0023(11) C12 0.0131(13) 0.0189(17) 0.0253(16) 0.0038(14) 0.0104(12) 0.0003(13) C13 0.0172(15) 0.0178(16) 0.0317(17) 0.0004(15) 0.0164(13) 0.0027(14) C14 0.0147(13) 0.0202(16) 0.0264(16) 0.0043(14) 0.0112(12) -0.0007(13) C15 0.0147(14) 0.0215(17) 0.0275(16) 0.0060(15) 0.0125(12) 0.0005(13) C16 0.0138(14) 0.029(2) 0.0361(18) -0.0001(17) 0.0144(13) 0.0010(15) C17 0.0186(15) 0.034(2) 0.037(2) 0.0009(17) 0.0088(14) -0.0038(15) C18 0.0276(16) 0.0291(19) 0.0320(18) 0.0017(16) 0.0173(14) 0.0032(16) C19 0.0131(14) 0.0209(18) 0.0247(16) 0.0007(15) 0.0102(12) -0.0004(14) C20 0.0155(14) 0.032(2) 0.0302(17) -0.0006(15) 0.0100(13) -0.0070(14) C21 0.0144(14) 0.0230(17) 0.0306(17) 0.0014(15) 0.0121(12) -0.0008(14) C22 0.0350(18) 0.030(2) 0.0354(19) -0.0036(17) 0.0191(16) -0.0028(17) C23 0.0271(18) 0.031(2) 0.0249(17) -0.0025(15) 0.0064(14) -0.0060(15) C24 0.0165(15) 0.0231(18) 0.0366(18) 0.0036(16) 0.0133(13) -0.0044(14) C25 0.030(2) 0.050(3) 0.039(2) 0.007(2) -0.0021(17) -0.017(2) C26 0.0140(14) 0.031(2) 0.0344(19) 0.0016(15) 0.0120(13) 0.0031(13) C27 0.0206(16) 0.040(2) 0.043(2) 0.002(2) 0.0141(15) -0.0012(17) C28 0.052(2) 0.042(2) 0.035(2) -0.008(2) 0.0184(18) -0.015(2) C29 0.0193(17) 0.055(3) 0.048(2) 0.010(2) 0.0085(16) -0.0032(19) _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 1.348(4) . ? N1 C3 1.450(4) . ? N1 H1 0.8800 . ? C2 N11 1.474(4) . ? C2 C12 1.506(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C19 1.513(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? N4 C7 1.361(4) . ? N4 C13 1.456(4) . ? N4 H4 0.8800 . ? O5 C7 1.239(4) . ? O6 C9 1.250(4) . ? C7 N11 1.347(4) . ? C8 C19 1.519(4) . ? C8 C12 1.522(4) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 N10 1.346(4) . ? N10 C15 1.469(4) . ? N10 H10 0.8800 . ? N11 H11 0.8800 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C24 1.513(4) . ? C13 C16 1.534(4) . ? C13 H13 1.0000 . ? C14 C21 1.391(4) . ? C14 C26 1.410(4) . ? C14 C15 1.509(5) . ? C15 C20 1.529(4) . ? C15 H15 1.0000 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C26 1.357(5) . ? C17 C23 1.390(5) . ? C17 H17 0.9500 . ? C18 C21 1.379(5) . ? C18 C23 1.390(5) . ? C18 H18 0.9500 . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21 0.9500 . ? C22 C28 1.364(5) . ? C22 C24 1.381(5) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? C24 C27 1.396(5) . ? C25 C29 1.363(6) . ? C25 C28 1.391(6) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 C29 1.375(5) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? C29 H29 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 N1 C3 121.2(3) . . ? C9 N1 H1 119.4 . . ? C3 N1 H1 119.4 . . ? N11 C2 C12 112.7(3) . . ? N11 C2 H2A 109.1 . . ? C12 C2 H2A 109.1 . . ? N11 C2 H2B 109.1 . . ? C12 C2 H2B 109.1 . . ? H2A C2 H2B 107.8 . . ? N1 C3 C19 113.3(3) . . ? N1 C3 H3A 108.9 . . ? C19 C3 H3A 108.9 . . ? N1 C3 H3B 108.9 . . ? C19 C3 H3B 108.9 . . ? H3A C3 H3B 107.7 . . ? C7 N4 C13 120.4(3) . . ? C7 N4 H4 119.8 . . ? C13 N4 H4 119.8 . . ? O5 C7 N11 121.6(3) . . ? O5 C7 N4 122.8(3) . . ? N11 C7 N4 115.6(3) . . ? C19 C8 C12 114.4(3) . . ? C19 C8 H8A 108.6 . . ? C12 C8 H8A 108.6 . . ? C19 C8 H8B 108.6 . . ? C12 C8 H8B 108.6 . . ? H8A C8 H8B 107.6 . . ? O6 C9 N10 122.4(3) . . ? O6 C9 N1 121.9(3) . . ? N10 C9 N1 115.8(3) . . ? C9 N10 C15 122.1(3) . . ? C9 N10 H10 118.9 . . ? C15 N10 H10 118.9 . . ? C7 N11 C2 119.3(3) . . ? C7 N11 H11 120.3 . . ? C2 N11 H11 120.3 . . ? C2 C12 C8 109.3(3) . . ? C2 C12 H12A 109.8 . . ? C8 C12 H12A 109.8 . . ? C2 C12 H12B 109.8 . . ? C8 C12 H12B 109.8 . . ? H12A C12 H12B 108.3 . . ? N4 C13 C24 113.4(3) . . ? N4 C13 C16 109.0(3) . . ? C24 C13 C16 110.6(3) . . ? N4 C13 H13 107.8 . . ? C24 C13 H13 107.8 . . ? C16 C13 H13 107.8 . . ? C21 C14 C26 117.3(3) . . ? C21 C14 C15 123.8(3) . . ? C26 C14 C15 118.9(3) . . ? N10 C15 C14 108.3(3) . . ? N10 C15 C20 111.4(3) . . ? C14 C15 C20 115.1(3) . . ? N10 C15 H15 107.3 . . ? C14 C15 H15 107.3 . . ? C20 C15 H15 107.3 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C26 C17 C23 121.1(3) . . ? C26 C17 H17 119.4 . . ? C23 C17 H17 119.4 . . ? C21 C18 C23 120.9(3) . . ? C21 C18 H18 119.5 . . ? C23 C18 H18 119.5 . . ? C3 C19 C8 109.6(3) . . ? C3 C19 H19A 109.7 . . ? C8 C19 H19A 109.7 . . ? C3 C19 H19B 109.7 . . ? C8 C19 H19B 109.7 . . ? H19A C19 H19B 108.2 . . ? C15 C20 H20A 109.5 . . ? C15 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C15 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C18 C21 C14 121.0(3) . . ? C18 C21 H21 119.5 . . ? C14 C21 H21 119.5 . . ? C28 C22 C24 122.3(4) . . ? C28 C22 H22 118.9 . . ? C24 C22 H22 118.9 . . ? C17 C23 C18 118.2(3) . . ? C17 C23 H23 120.9 . . ? C18 C23 H23 120.9 . . ? C22 C24 C27 117.6(3) . . ? C22 C24 C13 120.3(3) . . ? C27 C24 C13 122.1(3) . . ? C29 C25 C28 119.1(4) . . ? C29 C25 H25 120.5 . . ? C28 C25 H25 120.5 . . ? C17 C26 C14 121.4(3) . . ? C17 C26 H26 119.3 . . ? C14 C26 H26 119.3 . . ? C29 C27 C24 120.1(4) . . ? C29 C27 H27 120.0 . . ? C24 C27 H27 120.0 . . ? C22 C28 C25 119.5(4) . . ? C22 C28 H28 120.2 . . ? C25 C28 H28 120.2 . . ? C25 C29 C27 121.5(4) . . ? C25 C29 H29 119.3 . . ? C27 C29 H29 119.3 . . ? 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 C9 N1 C3 C19 160.2(3) . . . . ? C13 N4 C7 O5 -15.6(5) . . . . ? C13 N4 C7 N11 165.8(3) . . . . ? C3 N1 C9 O6 -1.4(5) . . . . ? C3 N1 C9 N10 179.6(3) . . . . ? O6 C9 N10 C15 -17.2(5) . . . . ? N1 C9 N10 C15 161.8(3) . . . . ? O5 C7 N11 C2 6.1(5) . . . . ? N4 C7 N11 C2 -175.3(3) . . . . ? C12 C2 N11 C7 179.0(3) . . . . ? N11 C2 C12 C8 179.8(2) . . . . ? C19 C8 C12 C2 -178.8(3) . . . . ? C7 N4 C13 C24 -80.3(4) . . . . ? C7 N4 C13 C16 155.9(3) . . . . ? C9 N10 C15 C14 -130.4(3) . . . . ? C9 N10 C15 C20 102.2(4) . . . . ? C21 C14 C15 N10 -122.1(3) . . . . ? C26 C14 C15 N10 57.6(4) . . . . ? C21 C14 C15 C20 3.2(5) . . . . ? C26 C14 C15 C20 -177.1(3) . . . . ? N1 C3 C19 C8 -175.5(3) . . . . ? C12 C8 C19 C3 -174.6(3) . . . . ? C23 C18 C21 C14 0.7(5) . . . . ? C26 C14 C21 C18 -0.7(5) . . . . ? C15 C14 C21 C18 179.0(3) . . . . ? C26 C17 C23 C18 -0.7(6) . . . . ? C21 C18 C23 C17 0.0(6) . . . . ? C28 C22 C24 C27 0.0(5) . . . . ? C28 C22 C24 C13 177.9(4) . . . . ? N4 C13 C24 C22 164.5(3) . . . . ? C16 C13 C24 C22 -72.6(4) . . . . ? N4 C13 C24 C27 -17.8(5) . . . . ? C16 C13 C24 C27 105.1(4) . . . . ? C23 C17 C26 C14 0.7(6) . . . . ? C21 C14 C26 C17 0.0(5) . . . . ? C15 C14 C26 C17 -179.8(3) . . . . ? C22 C24 C27 C29 0.5(5) . . . . ? C13 C24 C27 C29 -177.3(4) . . . . ? C24 C22 C28 C25 -0.7(6) . . . . ? C29 C25 C28 C22 0.9(6) . . . . ? C28 C25 C29 C27 -0.4(6) . . . . ? C24 C27 C29 C25 -0.3(6) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.362 _refine_diff_density_min -0.306 _refine_diff_density_rms 0.069 # Attachment '- 12.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 837366' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 12 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H26 N4 O2' _chemical_formula_sum 'C20 H26 N4 O2' _chemical_formula_weight 354.45 _chemical_absolute_configuration syn 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 P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 12.1914(14) _cell_length_b 4.6342(6) _cell_length_c 17.341(2) _cell_angle_alpha 90.00 _cell_angle_beta 107.849(5) _cell_angle_gamma 90.00 _cell_volume 932.57(19) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.262 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 380 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9673 _exptl_absorpt_correction_T_max 0.9917 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 Smart-6K _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7921 _diffrn_reflns_av_R_equivalents 0.2294 _diffrn_reflns_av_sigmaI/netI 0.2359 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.23 _diffrn_reflns_theta_max 28.24 _reflns_number_total 4407 _reflns_number_gt 2170 _reflns_threshold_expression >2sigma(I) _computing_data_collection Smart _computing_cell_refinement Saint _computing_data_reduction Saint _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Xseed _computing_publication_material Xseed _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. The crystal a incredible long thin needles that do not diffract well. This accounts for the poor data and the majority of the cifcheck errors. We feel that that data is of good enough quality for its intended use. ; _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^)+(0.1019P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4407 _refine_ls_number_parameters 235 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1602 _refine_ls_R_factor_gt 0.0972 _refine_ls_wR_factor_ref 0.2550 _refine_ls_wR_factor_gt 0.2219 _refine_ls_goodness_of_fit_ref 0.896 _refine_ls_restrained_S_all 0.896 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.3310(3) 0.7341(8) 0.9876(2) 0.0257(9) Uani 1 1 d . . . N1 N 0.2727(4) 0.3178(10) 0.9184(2) 0.0231(9) Uani 1 1 d . . . H1N H 0.2844 0.1308 0.9168 0.028 Uiso 1 1 calc R . . C1 C 0.0681(5) 0.4575(12) 0.8584(3) 0.0237(12) Uani 1 1 d . . . O2 O 0.5828(4) 0.2218(8) 1.3136(2) 0.0285(9) Uani 1 1 d . . . N2 N 0.4025(4) 0.3069(9) 1.0450(2) 0.0231(10) Uani 1 1 d . . . H2N H 0.3973 0.1178 1.0407 0.028 Uiso 1 1 calc R . . C2 C -0.0154(5) 0.6386(13) 0.8092(3) 0.0340(13) Uani 1 1 d . . . H2 H 0.0035 0.7536 0.7698 0.041 Uiso 1 1 calc R . . N3 N 0.5071(4) 0.6404(10) 1.2525(2) 0.0228(10) Uani 1 1 d . . . H3N H 0.5084 0.8300 1.2552 0.027 Uiso 1 1 calc R . . C3 C -0.1257(5) 0.6558(13) 0.8162(4) 0.0342(14) Uani 1 1 d . . . H3 H -0.1814 0.7805 0.7818 0.041 Uiso 1 1 calc R . . N4 N 0.6437(4) 0.6497(10) 1.3755(2) 0.0253(10) Uani 1 1 d . . . H4N H 0.6344 0.8382 1.3728 0.030 Uiso 1 1 calc R . . C4 C -0.1536(5) 0.4877(14) 0.8742(4) 0.0359(14) Uani 1 1 d . . . H4 H -0.2278 0.5019 0.8810 0.043 Uiso 1 1 calc R . . C5 C -0.0739(5) 0.3034(13) 0.9208(3) 0.0359(14) Uani 1 1 d . . . H5 H -0.0943 0.1831 0.9586 0.043 Uiso 1 1 calc R . . C6 C 0.0362(5) 0.2873(12) 0.9144(3) 0.0277(12) Uani 1 1 d . . . H6 H 0.0907 0.1591 0.9485 0.033 Uiso 1 1 calc R . . C7 C 0.1876(4) 0.4560(12) 0.8505(3) 0.0228(11) Uani 1 1 d . . . H7 H 0.2116 0.6618 0.8492 0.027 Uiso 1 1 calc R . . C8 C 0.1906(5) 0.3167(13) 0.7713(3) 0.0295(12) Uani 1 1 d . . . H8A H 0.2696 0.3208 0.7683 0.044 Uiso 1 1 calc R . . H8B H 0.1398 0.4237 0.7254 0.044 Uiso 1 1 calc R . . H8C H 0.1643 0.1163 0.7694 0.044 Uiso 1 1 calc R . . C9 C 0.3348(4) 0.4716(12) 0.9845(3) 0.0200(11) Uani 1 1 d . . . C10 C 0.4836(5) 0.4329(12) 1.1167(3) 0.0233(11) Uani 1 1 d . . . H10A H 0.5155 0.6126 1.1013 0.028 Uiso 1 1 calc R . . H10B H 0.5484 0.2970 1.1387 0.028 Uiso 1 1 calc R . . C11 C 0.4278(4) 0.5016(12) 1.1827(3) 0.0242(11) Uani 1 1 d . . . H11A H 0.3606 0.6294 1.1598 0.029 Uiso 1 1 calc R . . H11B H 0.3995 0.3203 1.2001 0.029 Uiso 1 1 calc R . . C12 C 0.5798(4) 0.4866(11) 1.3142(3) 0.0186(10) Uani 1 1 d . . . C13 C 0.7286(4) 0.5248(11) 1.4471(3) 0.0218(11) Uani 1 1 d . . . H13 H 0.6965 0.3402 1.4609 0.026 Uiso 1 1 calc R . . C14 C 0.8396(5) 0.4568(14) 1.4282(3) 0.0318(13) Uani 1 1 d . . . H14A H 0.8235 0.3204 1.3829 0.048 Uiso 1 1 calc R . . H14C H 0.8952 0.3711 1.4761 0.048 Uiso 1 1 calc R . . H14B H 0.8717 0.6350 1.4136 0.048 Uiso 1 1 calc R . . C15 C 0.7435(4) 0.7339(11) 1.5170(3) 0.0207(10) Uani 1 1 d . . . C16 C 0.8486(5) 0.8527(12) 1.5602(3) 0.0282(12) Uani 1 1 d . . . H16 H 0.9160 0.7977 1.5473 0.034 Uiso 1 1 calc R . . C17 C 0.8577(6) 1.0517(14) 1.6222(3) 0.0367(15) Uani 1 1 d . . . H17 H 0.9302 1.1349 1.6501 0.044 Uiso 1 1 calc R . . C18 C 0.7605(6) 1.1273(14) 1.6429(3) 0.0373(14) Uani 1 1 d . . . H18 H 0.7659 1.2626 1.6850 0.045 Uiso 1 1 calc R . . C19 C 0.6559(5) 1.0048(15) 1.6019(3) 0.0375(14) Uani 1 1 d . . . H19 H 0.5893 1.0552 1.6164 0.045 Uiso 1 1 calc R . . C20 C 0.6464(5) 0.8095(12) 1.5399(3) 0.0255(12) Uani 1 1 d . . . H20 H 0.5737 0.7260 1.5126 0.031 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 O1 0.031(2) 0.027(2) 0.0181(18) -0.0020(15) 0.0064(16) -0.0001(15) N1 0.026(2) 0.026(2) 0.0153(19) -0.0018(18) 0.0030(17) 0.0005(19) C1 0.034(3) 0.027(3) 0.0088(19) -0.0045(19) 0.004(2) -0.004(2) O2 0.039(2) 0.025(2) 0.0210(19) 0.0003(15) 0.0082(17) 0.0031(16) N2 0.028(2) 0.024(2) 0.018(2) -0.0022(18) 0.0072(18) -0.0016(19) C2 0.033(3) 0.047(4) 0.020(3) 0.005(2) 0.006(2) -0.001(3) N3 0.029(2) 0.024(2) 0.016(2) 0.0009(17) 0.0066(18) 0.0022(18) C3 0.032(3) 0.038(4) 0.030(3) 0.003(2) 0.006(3) 0.002(3) N4 0.036(3) 0.027(2) 0.015(2) 0.0010(17) 0.0092(19) 0.004(2) C4 0.034(3) 0.043(4) 0.034(3) -0.012(3) 0.016(3) -0.004(3) C5 0.043(4) 0.040(4) 0.031(3) 0.001(3) 0.021(3) -0.008(3) C6 0.035(3) 0.035(3) 0.015(2) 0.004(2) 0.011(2) 0.001(2) C7 0.027(3) 0.030(3) 0.011(2) -0.001(2) 0.006(2) 0.000(2) C8 0.028(3) 0.051(4) 0.014(2) 0.001(2) 0.013(2) 0.001(3) C9 0.018(2) 0.031(3) 0.016(2) -0.001(2) 0.012(2) -0.002(2) C10 0.027(3) 0.030(3) 0.014(2) -0.003(2) 0.007(2) -0.007(2) C11 0.025(3) 0.030(3) 0.019(2) -0.004(2) 0.009(2) 0.000(2) C12 0.024(3) 0.022(3) 0.013(2) -0.001(2) 0.012(2) -0.003(2) C13 0.027(3) 0.027(3) 0.013(2) 0.0072(19) 0.009(2) 0.001(2) C14 0.031(3) 0.048(4) 0.022(3) 0.009(3) 0.016(2) 0.010(3) C15 0.025(3) 0.027(3) 0.011(2) 0.0046(19) 0.006(2) -0.004(2) C16 0.022(3) 0.040(3) 0.024(3) 0.003(2) 0.009(2) -0.003(2) C17 0.040(3) 0.046(4) 0.020(3) 0.002(2) 0.001(3) -0.013(3) C18 0.052(4) 0.043(4) 0.017(2) 0.000(2) 0.010(3) -0.003(3) C19 0.039(4) 0.060(4) 0.022(3) 0.002(3) 0.021(3) 0.006(3) C20 0.026(3) 0.038(3) 0.013(2) 0.001(2) 0.008(2) -0.001(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 O1 C9 1.219(6) . ? N1 C9 1.365(6) . ? N1 C7 1.458(6) . ? N1 H1N 0.8800 . ? C1 C2 1.392(8) . ? C1 C6 1.396(7) . ? C1 C7 1.505(7) . ? O2 C12 1.228(6) . ? N2 C9 1.354(6) . ? N2 C10 1.453(6) . ? N2 H2N 0.8800 . ? C2 C3 1.388(9) . ? C2 H2 0.9500 . ? N3 C12 1.362(6) . ? N3 C11 1.448(6) . ? N3 H3N 0.8800 . ? C3 C4 1.395(9) . ? C3 H3 0.9500 . ? N4 C12 1.342(7) . ? N4 C13 1.469(6) . ? N4 H4N 0.8800 . ? C4 C5 1.359(9) . ? C4 H4 0.9500 . ? C5 C6 1.383(9) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.528(7) . ? C7 H7 1.0000 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C10 C11 1.533(7) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C13 C15 1.519(7) . ? C13 C14 1.519(7) . ? C13 H13 1.0000 . ? C14 H14A 0.9800 . ? C14 H14C 0.9800 . ? C14 H14B 0.9800 . ? C15 C16 1.385(7) . ? C15 C20 1.403(8) . ? C16 C17 1.395(8) . ? C16 H16 0.9500 . ? C17 C18 1.384(9) . ? C17 H17 0.9500 . ? C18 C19 1.378(9) . ? C18 H18 0.9500 . ? C19 C20 1.383(8) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 N1 C7 121.6(5) . . ? C9 N1 H1N 119.2 . . ? C7 N1 H1N 119.2 . . ? C2 C1 C6 117.4(5) . . ? C2 C1 C7 119.6(5) . . ? C6 C1 C7 123.0(5) . . ? C9 N2 C10 122.0(5) . . ? C9 N2 H2N 119.0 . . ? C10 N2 H2N 119.0 . . ? C3 C2 C1 121.8(6) . . ? C3 C2 H2 119.1 . . ? C1 C2 H2 119.1 . . ? C12 N3 C11 122.1(4) . . ? C12 N3 H3N 119.0 . . ? C11 N3 H3N 119.0 . . ? C2 C3 C4 119.2(6) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C12 N4 C13 122.3(4) . . ? C12 N4 H4N 118.8 . . ? C13 N4 H4N 118.8 . . ? C5 C4 C3 119.5(6) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? C4 C5 C6 121.4(6) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C5 C6 C1 120.6(5) . . ? C5 C6 H6 119.7 . . ? C1 C6 H6 119.7 . . ? N1 C7 C1 113.4(4) . . ? N1 C7 C8 109.5(4) . . ? C1 C7 C8 112.0(4) . . ? N1 C7 H7 107.2 . . ? C1 C7 H7 107.2 . . ? C8 C7 H7 107.2 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O1 C9 N2 123.4(5) . . ? O1 C9 N1 122.6(5) . . ? N2 C9 N1 113.9(5) . . ? N2 C10 C11 112.4(4) . . ? N2 C10 H10A 109.1 . . ? C11 C10 H10A 109.1 . . ? N2 C10 H10B 109.1 . . ? C11 C10 H10B 109.1 . . ? H10A C10 H10B 107.9 . . ? N3 C11 C10 112.4(4) . . ? N3 C11 H11A 109.1 . . ? C10 C11 H11A 109.1 . . ? N3 C11 H11B 109.1 . . ? C10 C11 H11B 109.1 . . ? H11A C11 H11B 107.9 . . ? O2 C12 N4 123.9(5) . . ? O2 C12 N3 122.0(5) . . ? N4 C12 N3 114.0(4) . . ? N4 C13 C15 107.7(4) . . ? N4 C13 C14 110.1(4) . . ? C15 C13 C14 114.1(5) . . ? N4 C13 H13 108.3 . . ? C15 C13 H13 108.3 . . ? C14 C13 H13 108.3 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? H14C C14 H14B 109.5 . . ? C16 C15 C20 118.0(5) . . ? C16 C15 C13 123.3(5) . . ? C20 C15 C13 118.7(4) . . ? C15 C16 C17 121.4(5) . . ? C15 C16 H16 119.3 . . ? C17 C16 H16 119.3 . . ? C18 C17 C16 119.7(5) . . ? C18 C17 H17 120.1 . . ? C16 C17 H17 120.1 . . ? C19 C18 C17 119.5(6) . . ? C19 C18 H18 120.3 . . ? C17 C18 H18 120.3 . . ? C18 C19 C20 121.0(6) . . ? C18 C19 H19 119.5 . . ? C20 C19 H19 119.5 . . ? C19 C20 C15 120.4(5) . . ? C19 C20 H20 119.8 . . ? C15 C20 H20 119.8 . . ? 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 C6 C1 C2 C3 1.4(8) . . . . ? C7 C1 C2 C3 -177.7(5) . . . . ? C1 C2 C3 C4 0.2(9) . . . . ? C2 C3 C4 C5 -2.2(9) . . . . ? C3 C4 C5 C6 2.7(9) . . . . ? C4 C5 C6 C1 -1.1(9) . . . . ? C2 C1 C6 C5 -0.9(8) . . . . ? C7 C1 C6 C5 178.1(5) . . . . ? C9 N1 C7 C1 -91.1(6) . . . . ? C9 N1 C7 C8 142.9(5) . . . . ? C2 C1 C7 N1 164.8(5) . . . . ? C6 C1 C7 N1 -14.2(7) . . . . ? C2 C1 C7 C8 -70.7(7) . . . . ? C6 C1 C7 C8 110.4(6) . . . . ? C10 N2 C9 O1 -4.8(7) . . . . ? C10 N2 C9 N1 173.6(5) . . . . ? C7 N1 C9 O1 -7.1(7) . . . . ? C7 N1 C9 N2 174.5(4) . . . . ? C9 N2 C10 C11 86.6(6) . . . . ? C12 N3 C11 C10 -85.9(6) . . . . ? N2 C10 C11 N3 -177.1(5) . . . . ? C13 N4 C12 O2 3.1(8) . . . . ? C13 N4 C12 N3 -179.0(4) . . . . ? C11 N3 C12 O2 0.7(8) . . . . ? C11 N3 C12 N4 -177.3(4) . . . . ? C12 N4 C13 C15 -154.7(5) . . . . ? C12 N4 C13 C14 80.4(6) . . . . ? N4 C13 C15 C16 -122.6(5) . . . . ? C14 C13 C15 C16 -0.1(7) . . . . ? N4 C13 C15 C20 58.0(6) . . . . ? C14 C13 C15 C20 -179.5(4) . . . . ? C20 C15 C16 C17 -2.8(8) . . . . ? C13 C15 C16 C17 177.8(5) . . . . ? C15 C16 C17 C18 1.7(8) . . . . ? C16 C17 C18 C19 0.0(9) . . . . ? C17 C18 C19 C20 -0.6(9) . . . . ? C18 C19 C20 C15 -0.5(9) . . . . ? C16 C15 C20 C19 2.2(7) . . . . ? C13 C15 C20 C19 -178.3(5) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 28.24 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.472 _refine_diff_density_min -0.377 _refine_diff_density_rms 0.103 # Attachment '- 14 form 2.CIF' data_3 _database_code_depnum_ccdc_archive 'CCDC 837367' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 14 form 2 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H30 N4 O2' _chemical_formula_sum 'C22 H30 N4 O2' _chemical_formula_weight 382.50 _chemical_absolute_configuration syn 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 P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 4.59140(10) _cell_length_b 19.6481(4) _cell_length_c 11.2393(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.8720(10) _cell_angle_gamma 90.00 _cell_volume 1013.81(4) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4487 _cell_measurement_theta_min 2.754 _cell_measurement_theta_max 29.068 _exptl_crystal_description Needle _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.253 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 412 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9193 _exptl_absorpt_correction_T_max 0.9959 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 Smart-6K _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18937 _diffrn_reflns_av_R_equivalents 0.0399 _diffrn_reflns_av_sigmaI/netI 0.0488 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 30.52 _reflns_number_total 3189 _reflns_number_gt 2763 _reflns_threshold_expression >2sigma(I) _computing_data_collection Smart _computing_cell_refinement Saint _computing_data_reduction Saint _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Xseed _computing_publication_material Xseed _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. Friedel pairs number are 3021 ; _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^)+(0.0510P)^2^+0.0544P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3189 _refine_ls_number_parameters 253 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0488 _refine_ls_R_factor_gt 0.0376 _refine_ls_wR_factor_ref 0.0944 _refine_ls_wR_factor_gt 0.0886 _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_restrained_S_all 1.104 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.0113(3) 0.52357(7) 0.43438(12) 0.0216(3) Uani 1 1 d . . . N1 N 0.4110(3) 0.53998(8) 0.33375(13) 0.0179(3) Uani 1 1 d . . . H1N H 0.5993 0.5317 0.3315 0.021 Uiso 1 1 calc R . . C1 C 0.4697(4) 0.56902(9) 0.12721(14) 0.0162(3) Uani 1 1 d . . . O2 O 0.2409(3) 0.30428(9) 1.00567(12) 0.0255(3) Uani 1 1 d . . . N2 N 0.4215(3) 0.49269(8) 0.52013(14) 0.0182(3) Uani 1 1 d . . . H2N H 0.6079 0.4846 0.5097 0.022 Uiso 1 1 calc R . . C2 C 0.5573(4) 0.50449(10) 0.09154(17) 0.0213(4) Uani 1 1 d . . . H2 H 0.4864 0.4656 0.1322 0.026 Uiso 1 1 calc R . . N3 N -0.1843(3) 0.30810(8) 0.90019(13) 0.0179(3) Uani 1 1 d . . . H3N H -0.3752 0.3042 0.9012 0.022 Uiso 1 1 calc R . . C3 C 0.7464(5) 0.49589(11) -0.00252(18) 0.0264(4) Uani 1 1 d . . . H3 H 0.8055 0.4515 -0.0254 0.032 Uiso 1 1 calc R . . N4 N -0.1909(3) 0.30044(10) 1.10357(13) 0.0210(3) Uani 1 1 d . . . H4N H -0.3819 0.2992 1.0958 0.025 Uiso 1 1 calc R . . C4 C 0.8487(5) 0.55234(12) -0.06288(18) 0.0281(4) Uani 1 1 d . . . H4 H 0.9799 0.5468 -0.1267 0.034 Uiso 1 1 calc R . . C5 C 0.7596(4) 0.61665(11) -0.03019(18) 0.0246(4) Uani 1 1 d . . . H5 H 0.8272 0.6553 -0.0725 0.029 Uiso 1 1 calc R . . C6 C 0.5707(4) 0.62519(10) 0.06481(17) 0.0203(4) Uani 1 1 d . . . H6 H 0.5107 0.6696 0.0870 0.024 Uiso 1 1 calc R . . C7 C 0.2704(4) 0.57552(9) 0.23386(15) 0.0163(3) Uani 1 1 d . . . H7 H 0.0847 0.5511 0.2142 0.020 Uiso 1 1 calc R . . C8 C 0.1940(5) 0.64862(11) 0.26586(18) 0.0245(4) Uani 1 1 d . . . H8A H 0.0667 0.6488 0.3351 0.037 Uiso 1 1 calc R . . H8B H 0.0933 0.6702 0.1983 0.037 Uiso 1 1 calc R . . H8C H 0.3729 0.6739 0.2848 0.037 Uiso 1 1 calc R . . C9 C 0.2587(4) 0.51944(9) 0.42960(16) 0.0162(3) Uani 1 1 d . . . C10 C 0.2915(4) 0.47723(9) 0.63385(15) 0.0172(3) Uani 1 1 d . . . H10A H 0.1206 0.5072 0.6446 0.021 Uiso 1 1 calc R . . H10B H 0.4344 0.4879 0.6980 0.021 Uiso 1 1 calc R . . C11 C 0.1948(4) 0.40368(10) 0.64717(16) 0.0183(3) Uani 1 1 d . . . H11A H 0.3660 0.3733 0.6410 0.022 Uiso 1 1 calc R . . H11B H 0.0565 0.3920 0.5819 0.022 Uiso 1 1 calc R . . C12 C 0.0491(4) 0.39227(9) 0.76647(16) 0.0176(3) Uani 1 1 d . . . H12A H -0.1260 0.4215 0.7706 0.021 Uiso 1 1 calc R . . H12B H 0.1849 0.4065 0.8311 0.021 Uiso 1 1 calc R . . C13 C -0.0403(4) 0.31847(9) 0.78723(16) 0.0177(3) Uani 1 1 d . . . H13A H -0.1730 0.3039 0.7218 0.021 Uiso 1 1 calc R . . H13B H 0.1354 0.2893 0.7848 0.021 Uiso 1 1 calc R . . C14 C -0.0308(4) 0.30428(10) 1.00407(16) 0.0177(3) Uani 1 1 d . . . C15 C -0.0638(4) 0.29825(11) 1.22373(16) 0.0196(4) Uani 1 1 d . . . H15 H 0.1264 0.2736 1.2194 0.024 Uiso 1 1 calc R . . C16 C -0.0021(5) 0.36983(11) 1.2694(2) 0.0295(5) Uani 1 1 d . . . H16A H 0.1295 0.3931 1.2149 0.044 Uiso 1 1 calc R . . H16B H 0.0890 0.3672 1.3487 0.044 Uiso 1 1 calc R . . H16C H -0.1853 0.3952 1.2740 0.044 Uiso 1 1 calc R . . C17 C -0.2655(4) 0.25635(10) 1.30164(16) 0.0180(3) Uani 1 1 d . . . C18 C -0.3768(4) 0.28049(11) 1.40851(17) 0.0232(4) Uani 1 1 d . . . H18 H -0.3262 0.3247 1.4359 0.028 Uiso 1 1 calc R . . C19 C -0.5624(5) 0.23977(12) 1.47519(18) 0.0270(4) Uani 1 1 d . . . H19 H -0.6370 0.2567 1.5478 0.032 Uiso 1 1 calc R . . C20 C -0.6394(4) 0.17550(11) 1.43765(18) 0.0257(4) Uani 1 1 d . . . H20 H -0.7649 0.1481 1.4840 0.031 Uiso 1 1 calc R . . C21 C -0.5310(4) 0.15120(11) 1.33104(18) 0.0245(4) Uani 1 1 d . . . H21 H -0.5840 0.1071 1.3037 0.029 Uiso 1 1 calc R . . C22 C -0.3451(4) 0.19130(10) 1.26418(17) 0.0215(4) Uani 1 1 d . . . H22 H -0.2711 0.1740 1.1917 0.026 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0129(6) 0.0320(8) 0.0199(6) 0.0051(6) 0.0025(5) -0.0001(5) N1 0.0122(6) 0.0266(8) 0.0149(7) 0.0066(6) 0.0018(5) 0.0012(6) C1 0.0146(7) 0.0220(9) 0.0119(7) 0.0017(6) -0.0003(6) 0.0002(6) O2 0.0119(5) 0.0435(8) 0.0212(6) 0.0084(6) 0.0013(5) -0.0007(6) N2 0.0137(6) 0.0250(8) 0.0159(7) 0.0063(6) 0.0029(5) 0.0001(6) C2 0.0254(9) 0.0196(9) 0.0189(8) 0.0018(7) 0.0032(7) -0.0005(7) N3 0.0134(6) 0.0252(8) 0.0152(7) 0.0041(6) 0.0014(5) -0.0021(6) C3 0.0331(10) 0.0250(10) 0.0213(9) -0.0025(8) 0.0053(8) 0.0061(8) N4 0.0130(6) 0.0352(9) 0.0148(7) 0.0055(7) -0.0006(5) -0.0012(6) C4 0.0296(10) 0.0369(12) 0.0180(9) 0.0033(8) 0.0092(8) 0.0032(9) C5 0.0264(10) 0.0277(10) 0.0198(9) 0.0062(8) 0.0054(7) -0.0025(8) C6 0.0225(9) 0.0191(9) 0.0194(8) 0.0025(7) 0.0020(7) 0.0005(7) C7 0.0162(8) 0.0199(8) 0.0129(7) 0.0025(6) 0.0028(6) 0.0025(6) C8 0.0323(10) 0.0227(9) 0.0187(8) 0.0002(7) 0.0049(7) 0.0069(8) C9 0.0149(7) 0.0168(8) 0.0169(8) 0.0010(6) 0.0024(6) 0.0004(6) C10 0.0194(8) 0.0184(8) 0.0137(8) 0.0029(6) 0.0018(6) -0.0015(7) C11 0.0221(8) 0.0183(8) 0.0146(8) 0.0015(6) 0.0050(6) -0.0031(7) C12 0.0204(8) 0.0179(8) 0.0147(8) 0.0015(6) 0.0040(6) -0.0012(7) C13 0.0196(8) 0.0190(8) 0.0147(8) 0.0018(6) 0.0026(6) -0.0034(6) C14 0.0152(7) 0.0211(8) 0.0167(8) 0.0033(7) 0.0011(6) -0.0006(7) C15 0.0161(7) 0.0275(9) 0.0151(8) 0.0043(7) -0.0001(6) -0.0023(7) C16 0.0329(11) 0.0285(11) 0.0271(10) 0.0037(8) -0.0024(9) -0.0097(9) C17 0.0144(8) 0.0230(9) 0.0164(8) 0.0041(7) -0.0013(6) 0.0019(6) C18 0.0264(9) 0.0249(9) 0.0182(9) -0.0002(7) 0.0024(7) -0.0023(7) C19 0.0305(11) 0.0328(11) 0.0178(9) 0.0006(8) 0.0061(8) -0.0001(9) C20 0.0263(10) 0.0287(10) 0.0223(10) 0.0076(8) 0.0051(8) -0.0028(8) C21 0.0282(10) 0.0196(9) 0.0258(9) 0.0022(8) 0.0008(7) 0.0002(8) C22 0.0247(9) 0.0217(9) 0.0180(8) -0.0007(7) 0.0034(7) 0.0039(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 O1 C9 1.244(2) . ? N1 C9 1.355(2) . ? N1 C7 1.464(2) . ? N1 H1N 0.8800 . ? C1 C2 1.391(3) . ? C1 C6 1.391(3) . ? C1 C7 1.525(2) . ? O2 C14 1.247(2) . ? N2 C9 1.359(2) . ? N2 C10 1.451(2) . ? N2 H2N 0.8800 . ? C2 C3 1.389(3) . ? C2 H2 0.9500 . ? N3 C14 1.357(2) . ? N3 C13 1.455(2) . ? N3 H3N 0.8800 . ? C3 C4 1.386(3) . ? C3 H3 0.9500 . ? N4 C14 1.350(2) . ? N4 C15 1.464(2) . ? N4 H4N 0.8800 . ? C4 C5 1.380(3) . ? C4 H4 0.9500 . ? C5 C6 1.396(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.523(3) . ? C7 H7 1.0000 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C10 C11 1.520(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.524(2) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.526(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C15 C16 1.522(3) . ? C15 C17 1.525(3) . ? C15 H15 1.0000 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C22 1.393(3) . ? C17 C18 1.396(3) . ? C18 C19 1.395(3) . ? C18 H18 0.9500 . ? C19 C20 1.376(3) . ? C19 H19 0.9500 . ? C20 C21 1.389(3) . ? C20 H20 0.9500 . ? C21 C22 1.390(3) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 N1 C7 121.67(14) . . ? C9 N1 H1N 119.2 . . ? C7 N1 H1N 119.2 . . ? C2 C1 C6 118.54(16) . . ? C2 C1 C7 118.85(16) . . ? C6 C1 C7 122.60(16) . . ? C9 N2 C10 120.78(14) . . ? C9 N2 H2N 119.6 . . ? C10 N2 H2N 119.6 . . ? C3 C2 C1 121.14(18) . . ? C3 C2 H2 119.4 . . ? C1 C2 H2 119.4 . . ? C14 N3 C13 121.43(14) . . ? C14 N3 H3N 119.3 . . ? C13 N3 H3N 119.3 . . ? C4 C3 C2 119.72(19) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C14 N4 C15 123.45(15) . . ? C14 N4 H4N 118.3 . . ? C15 N4 H4N 118.3 . . ? C5 C4 C3 119.91(18) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 120.25(18) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C1 C6 C5 120.41(18) . . ? C1 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? N1 C7 C8 111.67(15) . . ? N1 C7 C1 107.45(14) . . ? C8 C7 C1 114.07(15) . . ? N1 C7 H7 107.8 . . ? C8 C7 H7 107.8 . . ? C1 C7 H7 107.8 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O1 C9 N1 122.79(16) . . ? O1 C9 N2 121.99(16) . . ? N1 C9 N2 115.22(15) . . ? N2 C10 C11 114.24(15) . . ? N2 C10 H10A 108.7 . . ? C11 C10 H10A 108.7 . . ? N2 C10 H10B 108.7 . . ? C11 C10 H10B 108.7 . . ? H10A C10 H10B 107.6 . . ? C10 C11 C12 111.06(15) . . ? C10 C11 H11A 109.4 . . ? C12 C11 H11A 109.4 . . ? C10 C11 H11B 109.4 . . ? C12 C11 H11B 109.4 . . ? H11A C11 H11B 108.0 . . ? C11 C12 C13 113.39(15) . . ? C11 C12 H12A 108.9 . . ? C13 C12 H12A 108.9 . . ? C11 C12 H12B 108.9 . . ? C13 C12 H12B 108.9 . . ? H12A C12 H12B 107.7 . . ? N3 C13 C12 113.17(15) . . ? N3 C13 H13A 108.9 . . ? C12 C13 H13A 108.9 . . ? N3 C13 H13B 108.9 . . ? C12 C13 H13B 108.9 . . ? H13A C13 H13B 107.8 . . ? O2 C14 N4 123.05(16) . . ? O2 C14 N3 121.26(16) . . ? N4 C14 N3 115.69(15) . . ? N4 C15 C16 110.70(17) . . ? N4 C15 C17 107.96(15) . . ? C16 C15 C17 114.61(17) . . ? N4 C15 H15 107.8 . . ? C16 C15 H15 107.8 . . ? C17 C15 H15 107.8 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C22 C17 C18 118.30(17) . . ? C22 C17 C15 118.72(17) . . ? C18 C17 C15 122.97(18) . . ? C17 C18 C19 120.14(19) . . ? C17 C18 H18 119.9 . . ? C19 C18 H18 119.9 . . ? C20 C19 C18 121.2(2) . . ? C20 C19 H19 119.4 . . ? C18 C19 H19 119.4 . . ? C19 C20 C21 119.10(19) . . ? C19 C20 H20 120.5 . . ? C21 C20 H20 120.5 . . ? C20 C21 C22 120.2(2) . . ? C20 C21 H21 119.9 . . ? C22 C21 H21 119.9 . . ? C21 C22 C17 121.13(18) . . ? C21 C22 H22 119.4 . . ? C17 C22 H22 119.4 . . ? 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 C6 C1 C2 C3 1.4(3) . . . . ? C7 C1 C2 C3 -177.83(17) . . . . ? C1 C2 C3 C4 -0.5(3) . . . . ? C2 C3 C4 C5 -0.7(3) . . . . ? C3 C4 C5 C6 1.1(3) . . . . ? C2 C1 C6 C5 -1.1(3) . . . . ? C7 C1 C6 C5 178.16(17) . . . . ? C4 C5 C6 C1 -0.2(3) . . . . ? C9 N1 C7 C8 73.5(2) . . . . ? C9 N1 C7 C1 -160.66(16) . . . . ? C2 C1 C7 N1 54.6(2) . . . . ? C6 C1 C7 N1 -124.66(18) . . . . ? C2 C1 C7 C8 178.91(17) . . . . ? C6 C1 C7 C8 -0.3(2) . . . . ? C7 N1 C9 O1 6.8(3) . . . . ? C7 N1 C9 N2 -174.26(17) . . . . ? C10 N2 C9 O1 -9.5(3) . . . . ? C10 N2 C9 N1 171.65(16) . . . . ? C9 N2 C10 C11 95.4(2) . . . . ? N2 C10 C11 C12 -177.55(14) . . . . ? C10 C11 C12 C13 -177.38(16) . . . . ? C14 N3 C13 C12 -78.3(2) . . . . ? C11 C12 C13 N3 -178.86(15) . . . . ? C15 N4 C14 O2 2.2(3) . . . . ? C15 N4 C14 N3 -177.92(18) . . . . ? C13 N3 C14 O2 -5.6(3) . . . . ? C13 N3 C14 N4 174.53(17) . . . . ? C14 N4 C15 C16 85.0(2) . . . . ? C14 N4 C15 C17 -148.81(19) . . . . ? N4 C15 C17 C22 53.2(2) . . . . ? C16 C15 C17 C22 177.10(17) . . . . ? N4 C15 C17 C18 -126.08(19) . . . . ? C16 C15 C17 C18 -2.2(3) . . . . ? C22 C17 C18 C19 0.1(3) . . . . ? C15 C17 C18 C19 179.46(18) . . . . ? C17 C18 C19 C20 0.0(3) . . . . ? C18 C19 C20 C21 -0.4(3) . . . . ? C19 C20 C21 C22 0.6(3) . . . . ? C20 C21 C22 C17 -0.5(3) . . . . ? C18 C17 C22 C21 0.1(3) . . . . ? C15 C17 C22 C21 -179.26(17) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 30.52 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.338 _refine_diff_density_min -0.180 _refine_diff_density_rms 0.045 # Attachment '- 17.cif' data_5 _database_code_depnum_ccdc_archive 'CCDC 837368' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 17 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H36 N4 O2' _chemical_formula_sum 'C25 H36 N4 O2' _chemical_formula_weight 424.58 _chemical_absolute_configuration syn 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 P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 12.275(4) _cell_length_b 4.6302(15) _cell_length_c 20.791(7) _cell_angle_alpha 90.00 _cell_angle_beta 102.108(9) _cell_angle_gamma 90.00 _cell_volume 1155.4(7) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 945 _cell_measurement_theta_min 2.885 _cell_measurement_theta_max 30.080 _exptl_crystal_description 'flat needles' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.220 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 460 _exptl_absorpt_coefficient_mu 0.078 _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 120(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 Smart-6K _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15914 _diffrn_reflns_av_R_equivalents 0.1230 _diffrn_reflns_av_sigmaI/netI 0.1045 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.00 _diffrn_reflns_theta_max 30.12 _reflns_number_total 6468 _reflns_number_gt 5084 _reflns_threshold_expression >2sigma(I) _computing_data_collection Smart _computing_cell_refinement Saint _computing_data_reduction Saint _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Xseed _computing_publication_material Xseed _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^)+(0.0898P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6468 _refine_ls_number_parameters 280 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0789 _refine_ls_R_factor_gt 0.0625 _refine_ls_wR_factor_ref 0.1623 _refine_ls_wR_factor_gt 0.1518 _refine_ls_goodness_of_fit_ref 0.987 _refine_ls_restrained_S_all 0.987 _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 O1 O -0.71540(11) -0.2041(3) 0.31537(6) 0.0206(3) Uani 1 1 d . . . O2 O 0.21525(11) -0.2056(3) 0.68798(7) 0.0232(3) Uani 1 1 d . . . N1 N -0.79351(13) 0.2235(3) 0.27548(7) 0.0189(3) Uani 1 1 d . . . H1N H -0.8002 0.4078 0.2842 0.023 Uiso 1 1 calc R . . N2 N -0.63263(13) 0.2188(3) 0.35485(7) 0.0185(3) Uani 1 1 d . . . H2N H -0.6338 0.4086 0.3526 0.022 Uiso 1 1 calc R . . N3 N 0.13237(13) 0.2121(3) 0.64589(7) 0.0180(3) Uani 1 1 d . . . H3N H 0.1386 0.3992 0.6402 0.022 Uiso 1 1 calc R . . N4 N 0.30832(13) 0.2222(3) 0.71172(8) 0.0202(3) Uani 1 1 d . . . H4N H 0.3149 0.4008 0.6986 0.024 Uiso 1 1 calc R . . C1 C -0.86916(14) 0.2918(4) 0.15929(8) 0.0172(3) Uani 1 1 d . . . C2 C -0.96524(15) 0.4201(5) 0.12283(9) 0.0210(4) Uani 1 1 d . . . H2 H -1.0351 0.3840 0.1341 0.025 Uiso 1 1 calc R . . C3 C -0.95967(16) 0.6006(5) 0.07007(9) 0.0258(4) Uani 1 1 d . . . H3 H -1.0259 0.6859 0.0456 0.031 Uiso 1 1 calc R . . C4 C -0.85897(19) 0.6570(5) 0.05294(9) 0.0274(5) Uani 1 1 d . . . H4 H -0.8556 0.7816 0.0171 0.033 Uiso 1 1 calc R . . C5 C -0.76236(17) 0.5288(5) 0.08888(10) 0.0283(5) Uani 1 1 d . . . H5 H -0.6927 0.5647 0.0773 0.034 Uiso 1 1 calc R . . C6 C -0.76778(17) 0.3495(5) 0.14126(10) 0.0245(4) Uani 1 1 d . . . H6 H -0.7014 0.2639 0.1655 0.029 Uiso 1 1 calc R . . C7 C -0.86851(14) 0.0958(4) 0.21808(8) 0.0170(3) Uani 1 1 d . . . H7 H -0.8353 -0.0928 0.2087 0.020 Uiso 1 1 calc R . . C8 C -0.98274(16) 0.0317(5) 0.23236(9) 0.0245(4) Uani 1 1 d . . . H8A H -0.9743 -0.0930 0.2712 0.037 Uiso 1 1 calc R . . H8B H -1.0289 -0.0662 0.1944 0.037 Uiso 1 1 calc R . . H8C H -1.0186 0.2131 0.2407 0.037 Uiso 1 1 calc R . . C9 C -0.71408(13) 0.0636(4) 0.31533(8) 0.0147(3) Uani 1 1 d . . . C10 C -0.54357(14) 0.0752(4) 0.40077(8) 0.0182(4) Uani 1 1 d . . . H10A H -0.5243 -0.1069 0.3808 0.022 Uiso 1 1 calc R . . H10B H -0.5702 0.0253 0.4412 0.022 Uiso 1 1 calc R . . C11 C -0.43970(14) 0.2618(4) 0.41916(8) 0.0175(3) Uani 1 1 d . . . H11B H -0.4575 0.4406 0.4410 0.021 Uiso 1 1 calc R . . H11A H -0.4137 0.3172 0.3789 0.021 Uiso 1 1 calc R . . C12 C -0.34745(14) 0.0961(4) 0.46555(8) 0.0181(4) Uani 1 1 d . . . H12B H -0.3785 0.0156 0.5020 0.022 Uiso 1 1 calc R . . H12A H -0.3240 -0.0683 0.4412 0.022 Uiso 1 1 calc R . . C13 C -0.24497(13) 0.2759(5) 0.49468(8) 0.0182(4) Uani 1 1 d . . . H13B H -0.2674 0.4416 0.5191 0.022 Uiso 1 1 calc R . . H13A H -0.2119 0.3532 0.4587 0.022 Uiso 1 1 calc R . . C14 C -0.15817(14) 0.0956(4) 0.54102(8) 0.0177(3) Uani 1 1 d . . . H14B H -0.1928 0.0149 0.5760 0.021 Uiso 1 1 calc R . . H14A H -0.1362 -0.0687 0.5160 0.021 Uiso 1 1 calc R . . C15 C -0.05353(14) 0.2618(4) 0.57314(8) 0.0176(3) Uani 1 1 d . . . H15A H -0.0194 0.3491 0.5386 0.021 Uiso 1 1 calc R . . H15B H -0.0738 0.4198 0.6005 0.021 Uiso 1 1 calc R . . C16 C 0.02987(14) 0.0624(4) 0.61573(8) 0.0176(4) Uani 1 1 d . . . H16B H -0.0042 -0.0209 0.6507 0.021 Uiso 1 1 calc R . . H16A H 0.0479 -0.0988 0.5884 0.021 Uiso 1 1 calc R . . C17 C 0.21806(13) 0.0617(4) 0.68276(8) 0.0159(3) Uani 1 1 d . . . C18 C 0.39383(14) 0.1013(4) 0.76408(8) 0.0194(4) Uani 1 1 d . . . H18 H 0.4058 -0.1042 0.7524 0.023 Uiso 1 1 calc R . . C19 C 0.50322(15) 0.2630(6) 0.76699(10) 0.0260(4) Uani 1 1 d . . . H19A H 0.5231 0.2559 0.7238 0.039 Uiso 1 1 calc R . . H19B H 0.5623 0.1722 0.7998 0.039 Uiso 1 1 calc R . . H19C H 0.4944 0.4646 0.7793 0.039 Uiso 1 1 calc R . . C20 C 0.36195(15) 0.1023(5) 0.83105(9) 0.0217(4) Uani 1 1 d . . . C21 C 0.42190(19) -0.0677(5) 0.88139(10) 0.0320(5) Uani 1 1 d . . . H21 H 0.4802 -0.1875 0.8730 0.038 Uiso 1 1 calc R . . C22 C 0.3980(2) -0.0654(6) 0.94368(11) 0.0411(6) Uani 1 1 d . . . H22 H 0.4392 -0.1841 0.9775 0.049 Uiso 1 1 calc R . . C23 C 0.3135(2) 0.1114(7) 0.95642(11) 0.0415(6) Uani 1 1 d . . . H23 H 0.2969 0.1149 0.9991 0.050 Uiso 1 1 calc R . . C24 C 0.2534(2) 0.2825(7) 0.90670(12) 0.0393(6) Uani 1 1 d . . . H24 H 0.1956 0.4033 0.9153 0.047 Uiso 1 1 calc R . . C25 C 0.27729(17) 0.2784(6) 0.84427(11) 0.0305(4) Uani 1 1 d . . . H25 H 0.2357 0.3962 0.8104 0.037 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 O1 0.0179(6) 0.0135(6) 0.0280(7) 0.0000(5) -0.0006(5) -0.0003(5) O2 0.0192(6) 0.0158(6) 0.0315(7) -0.0012(6) -0.0018(5) 0.0016(5) N1 0.0161(7) 0.0133(7) 0.0232(7) -0.0034(6) -0.0056(5) 0.0006(6) N2 0.0141(7) 0.0129(7) 0.0245(7) 0.0015(6) -0.0050(5) 0.0003(5) N3 0.0121(7) 0.0137(7) 0.0254(7) 0.0009(6) -0.0023(5) -0.0003(5) N4 0.0139(7) 0.0163(7) 0.0261(7) 0.0019(6) -0.0054(6) 0.0002(6) C1 0.0131(7) 0.0176(8) 0.0197(7) -0.0040(7) 0.0009(6) -0.0001(7) C2 0.0141(8) 0.0249(10) 0.0227(8) -0.0022(8) 0.0010(6) -0.0003(7) C3 0.0226(9) 0.0295(10) 0.0227(8) 0.0014(8) -0.0015(7) 0.0017(8) C4 0.0309(11) 0.0273(11) 0.0234(9) 0.0024(8) 0.0044(8) -0.0038(9) C5 0.0221(10) 0.0340(12) 0.0309(10) -0.0005(9) 0.0106(7) -0.0038(8) C6 0.0172(9) 0.0274(11) 0.0285(9) -0.0002(8) 0.0038(7) -0.0004(7) C7 0.0141(7) 0.0170(8) 0.0183(7) -0.0033(7) -0.0002(6) -0.0022(7) C8 0.0181(9) 0.0323(11) 0.0232(8) 0.0013(8) 0.0044(6) -0.0069(8) C9 0.0115(7) 0.0155(9) 0.0168(7) -0.0012(6) 0.0021(6) -0.0001(6) C10 0.0115(7) 0.0174(9) 0.0229(8) 0.0045(7) -0.0024(6) -0.0001(7) C11 0.0103(7) 0.0189(8) 0.0215(8) 0.0028(7) -0.0004(6) -0.0013(7) C12 0.0104(7) 0.0181(9) 0.0234(8) 0.0016(7) -0.0018(6) -0.0002(6) C13 0.0110(7) 0.0203(9) 0.0219(8) 0.0032(7) 0.0004(6) -0.0010(7) C14 0.0102(7) 0.0187(9) 0.0225(8) 0.0003(7) -0.0006(6) -0.0006(6) C15 0.0104(7) 0.0189(9) 0.0216(8) 0.0021(7) -0.0011(6) -0.0002(7) C16 0.0113(7) 0.0177(9) 0.0218(8) 0.0002(7) -0.0009(6) -0.0011(6) C17 0.0118(8) 0.0165(9) 0.0188(7) -0.0013(6) 0.0022(6) -0.0001(6) C18 0.0113(7) 0.0192(8) 0.0250(8) -0.0005(8) -0.0026(6) 0.0029(7) C19 0.0117(8) 0.0360(11) 0.0292(9) -0.0008(9) 0.0013(6) -0.0001(8) C20 0.0148(8) 0.0211(9) 0.0275(8) -0.0032(8) 0.0007(6) -0.0039(7) C21 0.0329(12) 0.0306(11) 0.0295(10) 0.0018(9) -0.0003(8) 0.0010(10) C22 0.0503(15) 0.0408(14) 0.0302(11) 0.0057(11) 0.0037(10) -0.0070(13) C23 0.0462(14) 0.0492(15) 0.0333(11) -0.0035(11) 0.0175(10) -0.0205(13) C24 0.0261(11) 0.0495(15) 0.0454(13) -0.0088(12) 0.0146(9) -0.0078(11) C25 0.0171(9) 0.0403(12) 0.0346(10) -0.0011(10) 0.0066(7) -0.0001(9) _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 O1 C9 1.240(2) . ? O2 C17 1.244(2) . ? N1 C9 1.359(2) . ? N1 C7 1.470(2) . ? N1 H1N 0.8800 . ? N2 C9 1.359(2) . ? N2 C10 1.453(2) . ? N2 H2N 0.8800 . ? N3 C17 1.357(2) . ? N3 C16 1.458(2) . ? N3 H3N 0.8800 . ? N4 C17 1.365(2) . ? N4 C18 1.456(2) . ? N4 H4N 0.8800 . ? C1 C2 1.394(2) . ? C1 C6 1.399(3) . ? C1 C7 1.521(3) . ? C2 C3 1.392(3) . ? C2 H2 0.9500 . ? C3 C4 1.381(3) . ? C3 H3 0.9500 . ? C4 C5 1.395(3) . ? C4 H4 0.9500 . ? C5 C6 1.382(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.522(3) . ? C7 H7 1.0000 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C10 C11 1.521(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.531(2) . ? C11 H11B 0.9900 . ? C11 H11A 0.9900 . ? C12 C13 1.524(2) . ? C12 H12B 0.9900 . ? C12 H12A 0.9900 . ? C13 C14 1.526(2) . ? C13 H13B 0.9900 . ? C13 H13A 0.9900 . ? C14 C15 1.526(2) . ? C14 H14B 0.9900 . ? C14 H14A 0.9900 . ? C15 C16 1.518(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16B 0.9900 . ? C16 H16A 0.9900 . ? C18 C20 1.523(3) . ? C18 C19 1.527(3) . ? C18 H18 1.0000 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C21 1.391(3) . ? C20 C25 1.393(3) . ? C21 C22 1.387(3) . ? C21 H21 0.9500 . ? C22 C23 1.390(4) . ? C22 H22 0.9500 . ? C23 C24 1.386(4) . ? C23 H23 0.9500 . ? C24 C25 1.390(3) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 N1 C7 121.54(14) . . ? C9 N1 H1N 119.2 . . ? C7 N1 H1N 119.2 . . ? C9 N2 C10 120.80(15) . . ? C9 N2 H2N 119.6 . . ? C10 N2 H2N 119.6 . . ? C17 N3 C16 119.72(15) . . ? C17 N3 H3N 120.1 . . ? C16 N3 H3N 120.1 . . ? C17 N4 C18 120.78(16) . . ? C17 N4 H4N 119.6 . . ? C18 N4 H4N 119.6 . . ? C2 C1 C6 118.13(17) . . ? C2 C1 C7 123.55(16) . . ? C6 C1 C7 118.32(15) . . ? C3 C2 C1 120.58(18) . . ? C3 C2 H2 119.7 . . ? C1 C2 H2 119.7 . . ? C4 C3 C2 120.75(18) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 C5 119.2(2) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? C6 C5 C4 120.1(2) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C5 C6 C1 121.24(18) . . ? C5 C6 H6 119.4 . . ? C1 C6 H6 119.4 . . ? N1 C7 C1 108.01(14) . . ? N1 C7 C8 111.45(15) . . ? C1 C7 C8 115.04(15) . . ? N1 C7 H7 107.3 . . ? C1 C7 H7 107.3 . . ? C8 C7 H7 107.3 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O1 C9 N1 122.50(15) . . ? O1 C9 N2 122.44(15) . . ? N1 C9 N2 115.06(15) . . ? N2 C10 C11 112.38(15) . . ? N2 C10 H10A 109.1 . . ? C11 C10 H10A 109.1 . . ? N2 C10 H10B 109.1 . . ? C11 C10 H10B 109.1 . . ? H10A C10 H10B 107.9 . . ? C10 C11 C12 110.12(15) . . ? C10 C11 H11B 109.6 . . ? C12 C11 H11B 109.6 . . ? C10 C11 H11A 109.6 . . ? C12 C11 H11A 109.6 . . ? H11B C11 H11A 108.2 . . ? C13 C12 C11 114.62(16) . . ? C13 C12 H12B 108.6 . . ? C11 C12 H12B 108.6 . . ? C13 C12 H12A 108.6 . . ? C11 C12 H12A 108.6 . . ? H12B C12 H12A 107.6 . . ? C12 C13 C14 111.15(17) . . ? C12 C13 H13B 109.4 . . ? C14 C13 H13B 109.4 . . ? C12 C13 H13A 109.4 . . ? C14 C13 H13A 109.4 . . ? H13B C13 H13A 108.0 . . ? C15 C14 C13 114.34(16) . . ? C15 C14 H14B 108.7 . . ? C13 C14 H14B 108.7 . . ? C15 C14 H14A 108.7 . . ? C13 C14 H14A 108.7 . . ? H14B C14 H14A 107.6 . . ? C16 C15 C14 110.55(15) . . ? C16 C15 H15A 109.5 . . ? C14 C15 H15A 109.5 . . ? C16 C15 H15B 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 108.1 . . ? N3 C16 C15 112.15(15) . . ? N3 C16 H16B 109.2 . . ? C15 C16 H16B 109.2 . . ? N3 C16 H16A 109.2 . . ? C15 C16 H16A 109.2 . . ? H16B C16 H16A 107.9 . . ? O2 C17 N3 121.85(16) . . ? O2 C17 N4 122.56(15) . . ? N3 C17 N4 115.55(16) . . ? N4 C18 C20 113.51(16) . . ? N4 C18 C19 109.33(17) . . ? C20 C18 C19 110.76(15) . . ? N4 C18 H18 107.7 . . ? C20 C18 H18 107.7 . . ? C19 C18 H18 107.7 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 C20 C25 118.8(2) . . ? C21 C20 C18 119.30(18) . . ? C25 C20 C18 121.84(18) . . ? C22 C21 C20 121.1(2) . . ? C22 C21 H21 119.5 . . ? C20 C21 H21 119.5 . . ? C21 C22 C23 119.7(2) . . ? C21 C22 H22 120.2 . . ? C23 C22 H22 120.2 . . ? C24 C23 C22 119.8(2) . . ? C24 C23 H23 120.1 . . ? C22 C23 H23 120.1 . . ? C23 C24 C25 120.3(3) . . ? C23 C24 H24 119.8 . . ? C25 C24 H24 119.8 . . ? C24 C25 C20 120.3(2) . . ? C24 C25 H25 119.8 . . ? C20 C25 H25 119.8 . . ? 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 C6 C1 C2 C3 -0.1(3) . . . . ? C7 C1 C2 C3 179.12(18) . . . . ? C1 C2 C3 C4 -0.2(3) . . . . ? C2 C3 C4 C5 0.5(3) . . . . ? C3 C4 C5 C6 -0.5(3) . . . . ? C4 C5 C6 C1 0.2(3) . . . . ? C2 C1 C6 C5 0.1(3) . . . . ? C7 C1 C6 C5 -179.15(19) . . . . ? C9 N1 C7 C1 -131.35(18) . . . . ? C9 N1 C7 C8 101.4(2) . . . . ? C2 C1 C7 N1 -121.45(18) . . . . ? C6 C1 C7 N1 57.7(2) . . . . ? C2 C1 C7 C8 3.7(3) . . . . ? C6 C1 C7 C8 -177.07(17) . . . . ? C7 N1 C9 O1 -16.6(3) . . . . ? C7 N1 C9 N2 162.98(17) . . . . ? C10 N2 C9 O1 -1.5(3) . . . . ? C10 N2 C9 N1 178.89(17) . . . . ? C9 N2 C10 C11 156.61(17) . . . . ? N2 C10 C11 C12 -177.97(15) . . . . ? C10 C11 C12 C13 -172.00(16) . . . . ? C11 C12 C13 C14 179.13(15) . . . . ? C12 C13 C14 C15 -179.07(15) . . . . ? C13 C14 C15 C16 -177.40(16) . . . . ? C17 N3 C16 C15 -176.55(16) . . . . ? C14 C15 C16 N3 178.45(15) . . . . ? C16 N3 C17 O2 5.3(3) . . . . ? C16 N3 C17 N4 -176.80(16) . . . . ? C18 N4 C17 O2 -16.5(3) . . . . ? C18 N4 C17 N3 165.60(17) . . . . ? C17 N4 C18 C20 -79.8(2) . . . . ? C17 N4 C18 C19 155.99(18) . . . . ? N4 C18 C20 C21 164.26(18) . . . . ? C19 C18 C20 C21 -72.3(2) . . . . ? N4 C18 C20 C25 -18.5(3) . . . . ? C19 C18 C20 C25 104.9(2) . . . . ? C25 C20 C21 C22 0.5(3) . . . . ? C18 C20 C21 C22 177.8(2) . . . . ? C20 C21 C22 C23 -0.6(4) . . . . ? C21 C22 C23 C24 0.4(4) . . . . ? C22 C23 C24 C25 -0.1(4) . . . . ? C23 C24 C25 C20 0.0(4) . . . . ? C21 C20 C25 C24 -0.2(3) . . . . ? C18 C20 C25 C24 -177.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.463 _refine_diff_density_min -0.278 _refine_diff_density_rms 0.068