Supplementary Material (ESI) for Organic and Biomolecular Chemistry This journal is (C) The Royal Society of Chemistry 2006 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'R. Jones' 'Simon J. Coles' 'Michael B. Hursthouse' 'James N. Iley' 'Pedro M.J. Lory' _publ_contact_author_name 'Raymond C. F. Jones' _publ_contact_author_address ; Chemistry Department Loughborough University Loughborough Leics LE11 3TU UNITED KINGDOM ; _publ_contact_author_email R.C.F.JONES@LBORO.AC.UK _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Intramolecular 1,3-dipolar cycloadditions of dihydroimidazolium ylides: synthesis of pyrrolo[1,2,3-de]quinoxalines and imidazo[1,2-a]indoles ; data_s92_1 _database_code_depnum_ccdc_archive 'CCDC 156229' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H26 N2 O2' _chemical_formula_weight 386.48 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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.559(2) _cell_length_b 9.6567(19) _cell_length_c 11.052(2) _cell_angle_alpha 90.00 _cell_angle_beta 112.47(3) _cell_angle_gamma 90.00 _cell_volume 1041.5(4) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 12125 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.232 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 412 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type multi-scans _exptl_absorpt_correction_T_min 0.9807 _exptl_absorpt_correction_T_max 0.9922 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD Area Detector' _diffrn_measurement_method 'Phi and Omega scans to fill Ewald Sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12212 _diffrn_reflns_av_R_equivalents 0.0362 _diffrn_reflns_av_sigmaI/netI 0.0484 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4640 _reflns_number_gt 3968 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement 'DENZO, COLLECT' _computing_data_reduction 'DENZO, COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CAMERON (Watkin, Pearce 1995)' _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^)+(0.0470P)^2^+0.0171P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.031(3) _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 0.6(10) _refine_ls_number_reflns 4640 _refine_ls_number_parameters 264 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0507 _refine_ls_R_factor_gt 0.0373 _refine_ls_wR_factor_ref 0.0897 _refine_ls_wR_factor_gt 0.0836 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.011 _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 0.72182(11) 0.25769(13) 0.61448(11) 0.0230(2) Uani 1 1 d . . . N2 N 0.64861(11) 0.12170(12) 0.79966(11) 0.0258(3) Uani 1 1 d . . . O1 O 1.05872(12) 0.58390(13) 0.70151(12) 0.0489(3) Uani 1 1 d . . . O2 O 0.87378(11) 0.61408(12) 0.51625(11) 0.0436(3) Uani 1 1 d . . . C1 C 1.01379(14) 0.37654(15) 0.90065(14) 0.0285(3) Uani 1 1 d . . . H1A H 0.9959 0.4676 0.9321 0.034 Uiso 1 1 calc R . . H1B H 1.1063 0.3793 0.8977 0.034 Uiso 1 1 calc R . . C2 C 1.00875(15) 0.26281(17) 0.99559(15) 0.0307(3) Uani 1 1 d . . . H2A H 1.0598 0.1809 0.9849 0.037 Uiso 1 1 calc R . . H2B H 1.0547 0.2966 1.0866 0.037 Uiso 1 1 calc R . . C3 C 0.86202(14) 0.21982(15) 0.97300(13) 0.0263(3) Uani 1 1 d . . . H3A H 0.8630 0.1546 1.0425 0.032 Uiso 1 1 calc R . . H3B H 0.8084 0.3024 0.9773 0.032 Uiso 1 1 calc R . . C4 C 0.79499(13) 0.15079(14) 0.83944(13) 0.0251(3) Uani 1 1 d . . . H4 H 0.8443 0.0625 0.8391 0.030 Uiso 1 1 calc R . . C5 C 0.81309(13) 0.24842(14) 0.74260(13) 0.0225(3) Uani 1 1 d . . . C6 C 0.90905(13) 0.34975(14) 0.76598(13) 0.0230(3) Uani 1 1 d . . . C7 C 0.87436(14) 0.42576(14) 0.64708(14) 0.0235(3) Uani 1 1 d . . . C8 C 0.94687(16) 0.54611(16) 0.62728(14) 0.0299(3) Uani 1 1 d . . . C9 C 0.9403(2) 0.7330(2) 0.4872(2) 0.0605(6) Uani 1 1 d . . . H9A H 0.9700 0.7963 0.5622 0.091 Uiso 1 1 calc R . . H9B H 0.8758 0.7808 0.4100 0.091 Uiso 1 1 calc R . . H9C H 1.0201 0.7025 0.4696 0.091 Uiso 1 1 calc R . . C10 C 0.75768(14) 0.36670(14) 0.55650(13) 0.0241(3) Uani 1 1 d . . . H10 H 0.7106 0.3969 0.4689 0.029 Uiso 1 1 calc R . . C11 C 0.58937(13) 0.18625(16) 0.56737(13) 0.0255(3) Uani 1 1 d . . . H11 H 0.5174 0.2540 0.5664 0.031 Uiso 1 1 calc R . . C12 C 0.59606(15) 0.07123(15) 0.66456(13) 0.0284(3) Uani 1 1 d . . . H12A H 0.5032 0.0322 0.6427 0.034 Uiso 1 1 calc R . . H12B H 0.6561 -0.0040 0.6565 0.034 Uiso 1 1 calc R . . C13 C 0.54948(14) 0.12746(15) 0.43125(13) 0.0257(3) Uani 1 1 d . . . C14 C 0.64540(15) 0.06617(16) 0.39000(15) 0.0312(3) Uani 1 1 d . . . H14 H 0.7398 0.0675 0.4456 0.037 Uiso 1 1 calc R . . C15 C 0.60404(17) 0.00309(18) 0.26812(15) 0.0367(4) Uani 1 1 d . . . H15 H 0.6702 -0.0374 0.2400 0.044 Uiso 1 1 calc R . . C16 C 0.46695(17) -0.00081(18) 0.18780(15) 0.0370(4) Uani 1 1 d . . . H16 H 0.4385 -0.0455 0.1051 0.044 Uiso 1 1 calc R . . C17 C 0.37171(16) 0.05990(17) 0.22746(15) 0.0362(4) Uani 1 1 d . . . H17 H 0.2774 0.0576 0.1717 0.043 Uiso 1 1 calc R . . C18 C 0.41225(14) 0.12454(16) 0.34834(14) 0.0309(3) Uani 1 1 d . . . H18 H 0.3457 0.1671 0.3746 0.037 Uiso 1 1 calc R . . C19 C 0.62212(15) 0.01967(17) 0.88579(14) 0.0316(3) Uani 1 1 d . . . H19A H 0.6700 0.0484 0.9781 0.038 Uiso 1 1 calc R . . H19B H 0.6593 -0.0714 0.8745 0.038 Uiso 1 1 calc R . . C20 C 0.47122(15) 0.00583(16) 0.85602(13) 0.0282(3) Uani 1 1 d . . . C21 C 0.39532(16) 0.12084(17) 0.86013(15) 0.0371(4) Uani 1 1 d . . . H21 H 0.4383 0.2089 0.8805 0.044 Uiso 1 1 calc R . . C22 C 0.25612(18) 0.1085(2) 0.83465(18) 0.0457(4) Uani 1 1 d . . . H22 H 0.2046 0.1880 0.8382 0.055 Uiso 1 1 calc R . . C23 C 0.19316(18) -0.0185(2) 0.80440(17) 0.0462(5) Uani 1 1 d . . . H23 H 0.0981 -0.0268 0.7869 0.055 Uiso 1 1 calc R . . C24 C 0.26741(17) -0.13350(19) 0.79941(16) 0.0411(4) Uani 1 1 d . . . H24 H 0.2238 -0.2212 0.7783 0.049 Uiso 1 1 calc R . . C25 C 0.40617(16) -0.12151(16) 0.82519(14) 0.0322(4) Uani 1 1 d . . . H25 H 0.4572 -0.2014 0.8217 0.039 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 0.0230(6) 0.0243(6) 0.0206(6) -0.0012(5) 0.0069(5) -0.0040(5) N2 0.0259(6) 0.0288(6) 0.0213(6) 0.0016(5) 0.0076(4) -0.0061(5) O1 0.0418(7) 0.0475(7) 0.0455(7) 0.0055(6) 0.0036(5) -0.0235(6) O2 0.0461(6) 0.0382(6) 0.0378(6) 0.0111(5) 0.0065(5) -0.0164(6) C1 0.0270(7) 0.0259(8) 0.0285(7) -0.0029(6) 0.0060(6) -0.0031(6) C2 0.0297(7) 0.0299(7) 0.0264(7) -0.0015(6) 0.0039(6) -0.0013(7) C3 0.0291(7) 0.0248(8) 0.0229(7) 0.0003(6) 0.0074(6) 0.0010(6) C4 0.0257(7) 0.0243(8) 0.0238(7) 0.0005(6) 0.0076(6) -0.0004(6) C5 0.0233(7) 0.0218(7) 0.0222(7) -0.0011(6) 0.0085(5) 0.0008(6) C6 0.0229(6) 0.0194(7) 0.0274(7) -0.0035(6) 0.0103(5) -0.0003(6) C7 0.0242(7) 0.0212(7) 0.0265(7) -0.0026(6) 0.0112(6) 0.0009(6) C8 0.0343(8) 0.0278(8) 0.0281(8) -0.0016(6) 0.0125(6) -0.0050(6) C9 0.0727(14) 0.0456(12) 0.0530(12) 0.0167(9) 0.0126(10) -0.0278(10) C10 0.0275(7) 0.0226(7) 0.0238(7) 0.0016(6) 0.0116(6) 0.0005(6) C11 0.0230(7) 0.0290(7) 0.0237(7) -0.0013(6) 0.0080(6) -0.0052(6) C12 0.0300(7) 0.0292(8) 0.0250(7) -0.0017(6) 0.0094(6) -0.0091(6) C13 0.0274(7) 0.0253(7) 0.0234(7) 0.0011(6) 0.0087(5) -0.0072(6) C14 0.0287(7) 0.0311(8) 0.0304(8) -0.0037(6) 0.0074(6) -0.0019(6) C15 0.0433(9) 0.0338(8) 0.0349(8) -0.0054(7) 0.0173(7) 0.0009(8) C16 0.0498(10) 0.0340(8) 0.0238(7) -0.0043(7) 0.0102(7) -0.0114(8) C17 0.0324(8) 0.0423(9) 0.0275(8) -0.0014(7) 0.0043(6) -0.0129(7) C18 0.0272(7) 0.0364(8) 0.0277(8) 0.0021(7) 0.0089(6) -0.0050(7) C19 0.0349(8) 0.0321(8) 0.0272(7) 0.0048(7) 0.0113(6) -0.0043(7) C20 0.0344(8) 0.0308(8) 0.0215(7) 0.0014(6) 0.0129(6) -0.0066(7) C21 0.0441(9) 0.0317(8) 0.0391(9) 0.0011(8) 0.0200(7) -0.0035(8) C22 0.0462(9) 0.0480(11) 0.0517(10) 0.0069(9) 0.0285(8) 0.0094(9) C23 0.0346(9) 0.0660(13) 0.0422(10) 0.0054(9) 0.0194(8) -0.0077(9) C24 0.0441(9) 0.0483(11) 0.0339(8) -0.0037(8) 0.0185(7) -0.0193(9) C25 0.0409(8) 0.0318(8) 0.0282(8) -0.0017(7) 0.0180(7) -0.0076(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 C10 1.3593(18) . ? N1 C5 1.3780(18) . ? N1 C11 1.4651(17) . ? N2 C12 1.4635(18) . ? N2 C4 1.4635(17) . ? N2 C19 1.4693(18) . ? O1 C8 1.2086(19) . ? O2 C8 1.3449(19) . ? O2 C9 1.445(2) . ? C1 C6 1.499(2) . ? C1 C2 1.534(2) . ? C2 C3 1.530(2) . ? C3 C4 1.5251(19) . ? C4 C5 1.4924(19) . ? C5 C6 1.3605(19) . ? C6 C7 1.425(2) . ? C7 C10 1.379(2) . ? C7 C8 1.454(2) . ? C11 C13 1.5096(19) . ? C11 C12 1.528(2) . ? C13 C18 1.3876(19) . ? C13 C14 1.392(2) . ? C14 C15 1.388(2) . ? C15 C16 1.379(2) . ? C16 C17 1.373(2) . ? C17 C18 1.386(2) . ? C19 C20 1.505(2) . ? C20 C21 1.380(2) . ? C20 C25 1.386(2) . ? C21 C22 1.392(2) . ? C22 C23 1.375(3) . ? C23 C24 1.372(3) . ? C24 C25 1.386(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 C10 N1 C5 108.86(12) . . ? C10 N1 C11 126.67(11) . . ? C5 N1 C11 122.17(12) . . ? C12 N2 C4 108.39(11) . . ? C12 N2 C19 110.23(11) . . ? C4 N2 C19 112.01(11) . . ? C8 O2 C9 115.63(13) . . ? C6 C1 C2 110.51(12) . . ? C3 C2 C1 112.36(12) . . ? C4 C3 C2 110.07(12) . . ? N2 C4 C5 108.41(11) . . ? N2 C4 C3 114.89(11) . . ? C5 C4 C3 106.18(11) . . ? C6 C5 N1 109.03(12) . . ? C6 C5 C4 127.48(12) . . ? N1 C5 C4 123.16(12) . . ? C5 C6 C7 106.55(12) . . ? C5 C6 C1 121.73(12) . . ? C7 C6 C1 131.20(12) . . ? C10 C7 C6 107.44(12) . . ? C10 C7 C8 126.66(13) . . ? C6 C7 C8 125.86(13) . . ? O1 C8 O2 122.90(14) . . ? O1 C8 C7 125.00(14) . . ? O2 C8 C7 112.08(13) . . ? N1 C10 C7 108.09(12) . . ? N1 C11 C13 113.34(11) . . ? N1 C11 C12 108.12(11) . . ? C13 C11 C12 110.34(12) . . ? N2 C12 C11 111.89(12) . . ? C18 C13 C14 118.82(13) . . ? C18 C13 C11 119.28(12) . . ? C14 C13 C11 121.71(13) . . ? C15 C14 C13 120.40(14) . . ? C16 C15 C14 120.01(15) . . ? C17 C16 C15 119.97(15) . . ? C16 C17 C18 120.41(14) . . ? C17 C18 C13 120.38(14) . . ? N2 C19 C20 111.46(12) . . ? C21 C20 C25 118.84(14) . . ? C21 C20 C19 120.06(13) . . ? C25 C20 C19 121.09(14) . . ? C20 C21 C22 120.40(16) . . ? C23 C22 C21 120.04(18) . . ? C24 C23 C22 120.09(15) . . ? C23 C24 C25 119.95(16) . . ? C20 C25 C24 120.67(16) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.172 _refine_diff_density_min -0.147 _refine_diff_density_rms 0.037 data_s92_2 _database_code_depnum_ccdc_archive 'CCDC 156230' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H34 N2 O3' _chemical_formula_weight 446.57 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 5.8566(4) _cell_length_b 22.8548(18) _cell_length_c 9.1424(7) _cell_angle_alpha 90.00 _cell_angle_beta 92.913(6) _cell_angle_gamma 90.00 _cell_volume 1222.14(16) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3346 _cell_measurement_theta_min 3.48 _cell_measurement_theta_max 24.71 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.214 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9845 _exptl_absorpt_correction_T_max 0.9922 _exptl_absorpt_process_details SORTAV _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _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 6900 _diffrn_reflns_av_R_equivalents 0.0585 _diffrn_reflns_av_sigmaI/netI 0.0958 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.48 _diffrn_reflns_theta_max 24.71 _reflns_number_total 3346 _reflns_number_gt 2427 _reflns_threshold_expression >2sigma(I) _computing_data_collection COLLECT _computing_cell_refinement SCALEPACK _computing_data_reduction 'DENZO, SCALEPACK & COLLECT' _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^)+(0.0376P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.028(3) _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 0.0(16) _refine_ls_number_reflns 3346 _refine_ls_number_parameters 299 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0842 _refine_ls_R_factor_gt 0.0500 _refine_ls_wR_factor_ref 0.1075 _refine_ls_wR_factor_gt 0.0957 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _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 0.2271(6) 0.32867(17) 0.6307(4) 0.0334(9) Uani 1 1 d . . . H1 H 0.1173 0.3477 0.6963 0.040 Uiso 1 1 calc R . . C2 C 0.4085(6) 0.29560(18) 0.7225(4) 0.0395(10) Uani 1 1 d . . . H2A H 0.4655 0.3210 0.8042 0.047 Uiso 1 1 calc R . . H2B H 0.5389 0.2870 0.6611 0.047 Uiso 1 1 calc R . . C3 C 0.3217(7) 0.23837(19) 0.7854(4) 0.0517(11) Uani 1 1 d . . . H3A H 0.1992 0.2467 0.8532 0.062 Uiso 1 1 calc R . . H3B H 0.4480 0.2183 0.8413 0.062 Uiso 1 1 calc R . . C4 C 0.2290(7) 0.19892(19) 0.6606(4) 0.0504(11) Uani 1 1 d . . . H4A H 0.3536 0.1891 0.5956 0.061 Uiso 1 1 calc R . . H4B H 0.1708 0.1620 0.7015 0.061 Uiso 1 1 calc R . . C5 C 0.0416(7) 0.22924(18) 0.5750(4) 0.0403(10) Uani 1 1 d . . . C6 C 0.0960(5) 0.28981(17) 0.5184(4) 0.0325(9) Uani 1 1 d . . . H6 H -0.0481 0.3098 0.4824 0.039 Uiso 1 1 calc R . . C7 C 0.3220(6) 0.17703(18) 0.2273(4) 0.0393(10) Uani 1 1 d . . . H7 H 0.4507 0.1891 0.2873 0.047 Uiso 1 1 calc R . . C8 C 0.3148(7) 0.1218(2) 0.1703(4) 0.0481(11) Uani 1 1 d . . . H8 H 0.4391 0.0959 0.1915 0.058 Uiso 1 1 calc R . . C9 C 0.1311(8) 0.1028(2) 0.0828(4) 0.0527(12) Uani 1 1 d . . . H9 H 0.1294 0.0644 0.0430 0.063 Uiso 1 1 calc R . . C10 C -0.0492(8) 0.1400(2) 0.0537(5) 0.0537(12) Uani 1 1 d . . . H10 H -0.1771 0.1273 -0.0061 0.064 Uiso 1 1 calc R . . C11 C -0.0454(6) 0.1964(2) 0.1118(4) 0.0430(11) Uani 1 1 d . . . H11 H -0.1717 0.2217 0.0923 0.052 Uiso 1 1 calc R . . C12 C 0.1424(5) 0.21580(18) 0.1982(4) 0.0326(9) Uani 1 1 d . . . C13 C 0.1565(5) 0.27836(17) 0.2496(4) 0.0314(9) Uani 1 1 d . . . H13 H 0.0010 0.2965 0.2414 0.038 Uiso 1 1 calc R . . C14 C 0.3219(5) 0.31448(16) 0.1610(4) 0.0305(9) Uani 1 1 d . . . H14A H 0.4621 0.2920 0.1424 0.037 Uiso 1 1 calc R . . H14B H 0.2487 0.3272 0.0664 0.037 Uiso 1 1 calc R . . C15 C 0.4019(5) 0.33763(17) 0.4023(4) 0.0288(9) Uani 1 1 d . . . H15 H 0.5647 0.3249 0.4186 0.035 Uiso 1 1 calc R . . C16 C 0.3348(5) 0.37529(16) 0.5345(3) 0.0276(8) Uani 1 1 d . . . H16 H 0.4760 0.3912 0.5863 0.033 Uiso 1 1 calc R . . C17 C 0.1741(6) 0.42476(17) 0.4944(4) 0.0306(9) Uani 1 1 d . . . C18 C 0.1754(6) 0.52854(16) 0.4190(4) 0.0326(9) Uani 1 1 d . . . C19 C -0.0084(6) 0.52151(18) 0.2989(4) 0.0437(10) Uani 1 1 d . . . H19A H -0.1324 0.4974 0.3343 0.066 Uiso 1 1 calc R . . H19B H 0.0560 0.5025 0.2142 0.066 Uiso 1 1 calc R . . H19C H -0.0685 0.5601 0.2701 0.066 Uiso 1 1 calc R . . C20 C 0.3692(6) 0.5657(2) 0.3668(5) 0.0525(12) Uani 1 1 d . . . H20A H 0.4883 0.5693 0.4454 0.079 Uiso 1 1 calc R . . H20B H 0.3111 0.6047 0.3397 0.079 Uiso 1 1 calc R . . H20C H 0.4335 0.5472 0.2814 0.079 Uiso 1 1 calc R . . C21 C 0.0804(6) 0.5545(2) 0.5550(4) 0.0453(11) Uani 1 1 d . . . H21A H -0.0446 0.5299 0.5871 0.068 Uiso 1 1 calc R . . H21B H 0.0228 0.5940 0.5333 0.068 Uiso 1 1 calc R . . H21C H 0.2015 0.5565 0.6329 0.068 Uiso 1 1 calc R . . C22 C 0.5835(5) 0.39525(18) 0.2227(4) 0.0349(10) Uani 1 1 d . . . H22A H 0.7137 0.3678 0.2353 0.042 Uiso 1 1 calc R . . H22B H 0.6097 0.4275 0.2939 0.042 Uiso 1 1 calc R . . C23 C 0.5799(5) 0.42006(17) 0.0708(3) 0.0304(9) Uani 1 1 d . . . C24 C 0.7660(6) 0.41414(18) -0.0140(4) 0.0396(10) Uani 1 1 d . . . H24 H 0.8954 0.3930 0.0240 0.048 Uiso 1 1 calc R . . C25 C 0.7704(6) 0.43805(18) -0.1528(4) 0.0424(11) Uani 1 1 d . . . H25 H 0.9013 0.4334 -0.2089 0.051 Uiso 1 1 calc R . . C26 C 0.5845(6) 0.46851(18) -0.2087(4) 0.0371(10) Uani 1 1 d . . . H26 H 0.5861 0.4855 -0.3035 0.045 Uiso 1 1 calc R . . C27 C 0.3967(6) 0.4743(2) -0.1271(4) 0.0447(11) Uani 1 1 d . . . H27 H 0.2666 0.4949 -0.1662 0.054 Uiso 1 1 calc R . . C28 C 0.3943(6) 0.45060(18) 0.0113(4) 0.0395(10) Uani 1 1 d . . . H28 H 0.2627 0.4553 0.0667 0.047 Uiso 1 1 calc R . . N1 N 0.2547(4) 0.28570(13) 0.3995(3) 0.0280(7) Uani 1 1 d . . . N2 N 0.3727(4) 0.36433(13) 0.2573(3) 0.0270(7) Uani 1 1 d . . . O1 O -0.1486(5) 0.20881(14) 0.5557(3) 0.0596(9) Uani 1 1 d . . . O2 O -0.0317(4) 0.42254(12) 0.5005(3) 0.0378(6) Uani 1 1 d . . . O3 O 0.2908(3) 0.47213(11) 0.4553(2) 0.0331(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.037(2) 0.029(2) 0.034(2) 0.0022(17) 0.0048(15) 0.0063(17) C2 0.053(2) 0.039(3) 0.026(2) 0.0013(18) -0.0029(16) 0.003(2) C3 0.076(3) 0.034(3) 0.045(3) 0.006(2) 0.000(2) -0.001(2) C4 0.069(3) 0.034(3) 0.049(3) 0.008(2) 0.009(2) -0.003(2) C5 0.048(3) 0.035(3) 0.040(2) -0.0076(19) 0.0187(18) -0.002(2) C6 0.033(2) 0.032(2) 0.034(2) -0.0013(17) 0.0050(15) 0.0024(18) C7 0.044(2) 0.027(3) 0.046(2) -0.001(2) -0.0011(18) 0.0034(19) C8 0.062(3) 0.035(3) 0.047(3) -0.002(2) 0.003(2) 0.008(2) C9 0.084(3) 0.025(3) 0.049(3) -0.008(2) 0.008(2) -0.001(3) C10 0.065(3) 0.047(3) 0.048(3) -0.014(2) -0.005(2) -0.010(3) C11 0.039(2) 0.048(3) 0.042(2) -0.004(2) 0.0012(17) -0.003(2) C12 0.033(2) 0.034(3) 0.031(2) 0.0019(18) 0.0050(15) -0.0040(19) C13 0.0281(19) 0.031(3) 0.035(2) -0.0013(17) 0.0018(14) 0.0051(17) C14 0.0276(19) 0.034(3) 0.030(2) 0.0030(17) 0.0019(14) 0.0048(16) C15 0.0260(19) 0.028(2) 0.032(2) 0.0014(17) 0.0040(14) 0.0016(17) C16 0.0301(19) 0.024(2) 0.028(2) 0.0013(16) 0.0005(14) 0.0020(17) C17 0.035(2) 0.028(2) 0.028(2) -0.0052(17) -0.0017(15) -0.001(2) C18 0.034(2) 0.020(2) 0.044(2) 0.0030(17) 0.0054(16) 0.0055(17) C19 0.046(2) 0.041(3) 0.043(2) -0.0028(19) -0.0050(17) 0.010(2) C20 0.042(2) 0.039(3) 0.076(3) 0.016(2) 0.005(2) 0.002(2) C21 0.055(3) 0.038(3) 0.042(2) -0.0026(19) 0.0049(18) 0.007(2) C22 0.026(2) 0.044(3) 0.035(2) 0.0053(19) 0.0013(14) -0.0023(17) C23 0.0266(19) 0.036(2) 0.029(2) 0.0021(17) 0.0009(14) -0.0032(18) C24 0.031(2) 0.046(3) 0.043(2) 0.001(2) 0.0093(16) 0.002(2) C25 0.043(2) 0.051(3) 0.035(2) -0.009(2) 0.0202(17) -0.008(2) C26 0.048(2) 0.039(3) 0.025(2) -0.0015(18) 0.0000(17) -0.015(2) C27 0.039(2) 0.050(3) 0.044(3) 0.011(2) -0.0011(18) 0.001(2) C28 0.034(2) 0.043(3) 0.042(2) 0.0085(19) 0.0074(16) 0.0014(19) N1 0.0285(15) 0.030(2) 0.0260(16) -0.0020(13) 0.0026(11) -0.0030(14) N2 0.0253(16) 0.029(2) 0.0261(17) -0.0001(14) -0.0006(12) -0.0035(14) O1 0.0501(18) 0.051(2) 0.079(2) 0.0050(17) 0.0156(14) -0.0152(16) O2 0.0328(15) 0.0368(17) 0.0443(15) 0.0042(12) 0.0060(10) 0.0013(13) O3 0.0327(13) 0.0226(16) 0.0439(14) 0.0004(12) 0.0012(10) 0.0001(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.521(5) . ? C1 C6 1.534(5) . ? C1 C16 1.537(5) . ? C2 C3 1.526(6) . ? C3 C4 1.532(6) . ? C4 C5 1.487(5) . ? C5 O1 1.213(4) . ? C5 C6 1.517(5) . ? C6 N1 1.468(4) . ? C7 C8 1.365(6) . ? C7 C12 1.391(5) . ? C8 C9 1.378(5) . ? C9 C10 1.371(6) . ? C10 C11 1.393(6) . ? C11 C12 1.394(5) . ? C12 C13 1.506(5) . ? C13 N1 1.469(4) . ? C13 C14 1.535(5) . ? C14 N2 1.461(4) . ? C15 N2 1.462(4) . ? C15 N1 1.467(4) . ? C15 C16 1.550(5) . ? C16 C17 1.505(5) . ? C17 O2 1.211(4) . ? C17 O3 1.338(4) . ? C18 O3 1.485(4) . ? C18 C19 1.507(5) . ? C18 C21 1.510(5) . ? C18 C20 1.514(5) . ? C22 N2 1.471(4) . ? C22 C23 1.500(5) . ? C23 C24 1.376(4) . ? C23 C28 1.380(5) . ? C24 C25 1.384(5) . ? C25 C26 1.369(5) . ? C26 C27 1.366(5) . ? C27 C28 1.378(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 113.2(3) . . ? C2 C1 C16 111.4(3) . . ? C6 C1 C16 102.9(3) . . ? C1 C2 C3 113.4(3) . . ? C2 C3 C4 109.6(3) . . ? C5 C4 C3 110.0(4) . . ? O1 C5 C4 123.1(4) . . ? O1 C5 C6 120.6(4) . . ? C4 C5 C6 116.3(3) . . ? N1 C6 C5 110.2(3) . . ? N1 C6 C1 102.6(3) . . ? C5 C6 C1 114.0(3) . . ? C8 C7 C12 120.5(3) . . ? C7 C8 C9 121.4(4) . . ? C10 C9 C8 119.2(4) . . ? C9 C10 C11 120.2(4) . . ? C10 C11 C12 120.5(4) . . ? C7 C12 C11 118.2(4) . . ? C7 C12 C13 121.1(3) . . ? C11 C12 C13 120.6(3) . . ? N1 C13 C12 114.3(3) . . ? N1 C13 C14 101.7(3) . . ? C12 C13 C14 111.8(3) . . ? N2 C14 C13 102.5(3) . . ? N2 C15 N1 106.3(2) . . ? N2 C15 C16 116.9(3) . . ? N1 C15 C16 106.9(3) . . ? C17 C16 C1 113.0(3) . . ? C17 C16 C15 114.1(3) . . ? C1 C16 C15 100.9(3) . . ? O2 C17 O3 124.7(3) . . ? O2 C17 C16 124.7(3) . . ? O3 C17 C16 110.6(3) . . ? O3 C18 C19 111.7(3) . . ? O3 C18 C21 109.9(3) . . ? C19 C18 C21 111.3(3) . . ? O3 C18 C20 102.6(3) . . ? C19 C18 C20 110.5(3) . . ? C21 C18 C20 110.6(3) . . ? N2 C22 C23 114.1(3) . . ? C24 C23 C28 117.3(3) . . ? C24 C23 C22 120.7(3) . . ? C28 C23 C22 122.0(3) . . ? C23 C24 C25 122.0(3) . . ? C26 C25 C24 119.5(3) . . ? C27 C26 C25 119.5(3) . . ? C26 C27 C28 120.6(4) . . ? C27 C28 C23 121.1(3) . . ? C15 N1 C6 109.2(3) . . ? C15 N1 C13 108.1(3) . . ? C6 N1 C13 117.7(2) . . ? C14 N2 C15 103.4(3) . . ? C14 N2 C22 113.1(2) . . ? C15 N2 C22 109.5(2) . . ? C17 O3 C18 122.0(3) . . ? _diffrn_measured_fraction_theta_max 0.940 _diffrn_reflns_theta_full 24.71 _diffrn_measured_fraction_theta_full 0.940 _refine_diff_density_max 0.181 _refine_diff_density_min -0.178 _refine_diff_density_rms 0.041 data_03HUR485 _database_code_depnum_ccdc_archive 'CCDC 216327' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H24 N2 O2' _chemical_formula_weight 324.41 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 5.3447(11) _cell_length_b 10.854(2) _cell_length_c 14.722(3) _cell_angle_alpha 81.91(3) _cell_angle_beta 87.82(3) _cell_angle_gamma 88.80(3) _cell_volume 844.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7239 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 27.48 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.275 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type multi-scans _exptl_absorpt_correction_T_min 0.9756 _exptl_absorpt_correction_T_max 0.9983 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD Area Detector' _diffrn_measurement_method 'Phi and Omega scans to fill Ewald Sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12313 _diffrn_reflns_av_R_equivalents 0.1814 _diffrn_reflns_av_sigmaI/netI 0.1771 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 27.43 _reflns_number_total 3729 _reflns_number_gt 1806 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement 'DENZO, COLLECT' _computing_data_reduction 'DENZO, COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CAMERON (Watkin, Pearce 1995)' _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^)+(0.0161P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.017(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3729 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1507 _refine_ls_R_factor_gt 0.0566 _refine_ls_wR_factor_ref 0.1318 _refine_ls_wR_factor_gt 0.1034 _refine_ls_goodness_of_fit_ref 0.944 _refine_ls_restrained_S_all 0.944 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -1.1992(4) 1.2141(2) 0.35155(17) 0.0321(6) Uani 1 1 d . . . H1 H -1.3223 1.1779 0.3191 0.039 Uiso 1 1 calc R . . C2 C -1.2284(4) 1.3363(2) 0.36735(17) 0.0334(6) Uani 1 1 d . . . H2 H -1.3706 1.3836 0.3453 0.040 Uiso 1 1 calc R . . C3 C -1.0532(4) 1.3898(2) 0.41468(17) 0.0334(6) Uani 1 1 d . . . H3 H -1.0724 1.4742 0.4245 0.040 Uiso 1 1 calc R . . C4 C -0.8484(4) 1.3199(2) 0.44800(17) 0.0344(6) Uani 1 1 d . . . H4 H -0.7287 1.3555 0.4823 0.041 Uiso 1 1 calc R . . C5 C -0.8184(4) 1.1984(2) 0.43128(17) 0.0319(6) Uani 1 1 d . . . H5 H -0.6760 1.1515 0.4536 0.038 Uiso 1 1 calc R . . C6 C -0.9917(4) 1.1437(2) 0.38267(16) 0.0272(6) Uani 1 1 d . . . C7 C -0.9505(4) 1.0137(2) 0.36123(17) 0.0321(6) Uani 1 1 d . . . H7A H -0.9205 0.9574 0.4189 0.038 Uiso 1 1 calc R . . H7B H -1.1038 0.9861 0.3348 0.038 Uiso 1 1 calc R . . C8 C -0.7872(4) 1.08013(19) 0.20739(15) 0.0276(6) Uani 1 1 d . . . H8A H -0.8422 1.1647 0.2182 0.033 Uiso 1 1 calc R . . H8B H -0.9249 1.0427 0.1780 0.033 Uiso 1 1 calc R . . C9 C -0.5592(4) 1.08946(18) 0.14389(16) 0.0277(6) Uani 1 1 d . . . H9A H -0.6043 1.1310 0.0823 0.033 Uiso 1 1 calc R . . H9B H -0.4308 1.1398 0.1677 0.033 Uiso 1 1 calc R . . C10 C -0.5080(4) 0.86677(19) 0.20607(15) 0.0246(6) Uani 1 1 d . . . C11 C -0.7037(4) 0.87329(19) 0.27897(16) 0.0258(6) Uani 1 1 d . . . H11 H -0.8649 0.8453 0.2570 0.031 Uiso 1 1 calc R . . C12 C -0.6256(4) 0.7805(2) 0.36118(16) 0.0316(6) Uani 1 1 d . . . H12A H -0.4750 0.8106 0.3878 0.038 Uiso 1 1 calc R . . H12B H -0.7620 0.7727 0.4090 0.038 Uiso 1 1 calc R . . C13 C -0.5692(4) 0.6539(2) 0.33046(17) 0.0303(6) Uani 1 1 d . . . H13A H -0.7195 0.6265 0.3020 0.036 Uiso 1 1 calc R . . H13B H -0.5354 0.5927 0.3852 0.036 Uiso 1 1 calc R . . C14 C -0.3465(4) 0.6536(2) 0.26212(16) 0.0293(6) Uani 1 1 d . . . H14A H -0.1885 0.6483 0.2955 0.035 Uiso 1 1 calc R . . H14B H -0.3542 0.5797 0.2298 0.035 Uiso 1 1 calc R . . C15 C -0.3494(4) 0.76988(19) 0.19331(15) 0.0243(5) Uani 1 1 d . . . C16 C -0.2000(4) 0.80953(19) 0.11258(16) 0.0242(6) Uani 1 1 d . . . C17 C -0.2721(4) 0.93069(19) 0.08155(16) 0.0269(6) Uani 1 1 d . . . H17 H -0.2016 0.9817 0.0295 0.032 Uiso 1 1 calc R . . C18 C -0.0040(4) 0.7439(2) 0.06744(17) 0.0287(6) Uani 1 1 d . . . C19 C 0.2445(4) 0.55762(19) 0.07632(18) 0.0350(7) Uani 1 1 d . . . H19A H 0.4056 0.5995 0.0805 0.042 Uiso 1 1 calc R . . H19B H 0.2182 0.5503 0.0111 0.042 Uiso 1 1 calc R . . C20 C 0.2471(4) 0.4307(2) 0.13313(19) 0.0435(7) Uani 1 1 d . . . H20A H 0.2672 0.4395 0.1978 0.065 Uiso 1 1 calc R . . H20B H 0.3867 0.3808 0.1119 0.065 Uiso 1 1 calc R . . H20C H 0.0889 0.3892 0.1267 0.065 Uiso 1 1 calc R . . N1 N -0.7369(3) 1.00382(15) 0.29635(12) 0.0244(5) Uani 1 1 d . . . N2 N -0.4589(3) 0.96426(16) 0.13732(13) 0.0254(5) Uani 1 1 d . . . O1 O 0.1147(3) 0.78315(14) -0.00230(12) 0.0399(5) Uani 1 1 d . . . O2 O 0.0404(3) 0.62800(13) 0.11306(11) 0.0332(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0294(13) 0.0325(15) 0.0338(16) -0.0025(12) -0.0012(11) -0.0009(10) C2 0.0320(13) 0.0333(15) 0.0323(16) 0.0021(12) 0.0045(11) 0.0052(10) C3 0.0414(14) 0.0257(14) 0.0313(16) 0.0006(12) 0.0072(11) -0.0015(11) C4 0.0350(14) 0.0353(16) 0.0334(16) -0.0063(12) -0.0008(11) -0.0054(11) C5 0.0282(13) 0.0345(15) 0.0316(16) -0.0008(12) 0.0029(11) 0.0027(10) C6 0.0287(13) 0.0253(14) 0.0251(15) 0.0026(11) 0.0083(10) -0.0028(10) C7 0.0347(13) 0.0269(14) 0.0330(16) -0.0006(12) 0.0078(11) -0.0037(10) C8 0.0332(13) 0.0240(13) 0.0247(15) -0.0008(11) -0.0011(10) 0.0037(9) C9 0.0402(13) 0.0193(13) 0.0220(14) 0.0021(11) 0.0005(10) 0.0019(9) C10 0.0302(12) 0.0209(13) 0.0210(14) 0.0033(10) -0.0022(10) -0.0008(9) C11 0.0307(12) 0.0189(13) 0.0268(15) 0.0001(11) -0.0007(10) -0.0008(9) C12 0.0343(13) 0.0285(14) 0.0294(16) 0.0032(12) 0.0055(11) 0.0002(10) C13 0.0314(13) 0.0254(14) 0.0312(16) 0.0058(11) 0.0011(10) -0.0008(10) C14 0.0331(12) 0.0223(13) 0.0313(16) 0.0004(11) 0.0007(10) 0.0007(9) C15 0.0261(12) 0.0224(13) 0.0235(14) 0.0006(10) -0.0009(10) -0.0022(9) C16 0.0262(12) 0.0201(13) 0.0258(15) -0.0019(11) -0.0017(10) -0.0015(9) C17 0.0304(13) 0.0268(14) 0.0222(14) 0.0003(11) 0.0017(10) -0.0007(10) C18 0.0329(13) 0.0227(14) 0.0295(16) -0.0002(12) -0.0017(11) -0.0015(10) C19 0.0318(13) 0.0272(15) 0.0448(18) -0.0039(13) 0.0072(11) 0.0038(10) C20 0.0474(15) 0.0285(15) 0.053(2) -0.0024(13) 0.0010(13) 0.0109(11) N1 0.0269(10) 0.0223(11) 0.0224(12) 0.0008(9) 0.0040(8) 0.0009(7) N2 0.0318(11) 0.0197(11) 0.0234(12) 0.0001(9) 0.0019(8) 0.0040(8) O1 0.0478(10) 0.0299(10) 0.0377(12) 0.0049(8) 0.0163(8) 0.0023(7) O2 0.0371(9) 0.0239(9) 0.0360(11) 0.0017(8) 0.0065(7) 0.0070(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 C2 1.384(3) . ? C1 C6 1.388(3) . ? C2 C3 1.373(3) . ? C3 C4 1.384(3) . ? C4 C5 1.380(3) . ? C5 C6 1.384(3) . ? C6 C7 1.499(3) . ? C7 N1 1.473(3) . ? C8 N1 1.478(2) . ? C8 C9 1.504(3) . ? C9 N2 1.465(3) . ? C10 C15 1.366(3) . ? C10 N2 1.379(2) . ? C10 C11 1.478(3) . ? C11 N1 1.481(3) . ? C11 C12 1.527(3) . ? C12 C13 1.527(3) . ? C13 C14 1.529(3) . ? C14 C15 1.504(3) . ? C15 C16 1.426(3) . ? C16 C17 1.382(3) . ? C16 C18 1.447(3) . ? C17 N2 1.345(3) . ? C18 O1 1.215(3) . ? C18 O2 1.361(2) . ? C19 O2 1.450(3) . ? C19 C20 1.508(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 120.6(2) . . ? C3 C2 C1 120.5(2) . . ? C2 C3 C4 119.6(2) . . ? C5 C4 C3 119.8(2) . . ? C4 C5 C6 121.3(2) . . ? C5 C6 C1 118.2(2) . . ? C5 C6 C7 120.67(19) . . ? C1 C6 C7 121.1(2) . . ? N1 C7 C6 112.45(17) . . ? N1 C8 C9 111.70(15) . . ? N2 C9 C8 109.26(16) . . ? C15 C10 N2 108.56(19) . . ? C15 C10 C11 128.51(19) . . ? N2 C10 C11 122.94(18) . . ? C10 C11 N1 109.44(17) . . ? C10 C11 C12 106.57(17) . . ? N1 C11 C12 115.5(2) . . ? C13 C12 C11 109.6(2) . . ? C12 C13 C14 113.96(18) . . ? C15 C14 C13 110.44(17) . . ? C10 C15 C16 106.65(18) . . ? C10 C15 C14 120.6(2) . . ? C16 C15 C14 132.7(2) . . ? C17 C16 C15 107.0(2) . . ? C17 C16 C18 123.0(2) . . ? C15 C16 C18 130.07(19) . . ? N2 C17 C16 108.58(19) . . ? O1 C18 O2 121.3(2) . . ? O1 C18 C16 126.6(2) . . ? O2 C18 C16 112.03(19) . . ? O2 C19 C20 106.82(18) . . ? C7 N1 C8 109.77(15) . . ? C7 N1 C11 109.88(16) . . ? C8 N1 C11 107.28(18) . . ? C17 N2 C10 109.21(16) . . ? C17 N2 C9 128.21(18) . . ? C10 N2 C9 120.88(19) . . ? C18 O2 C19 116.20(17) . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 27.43 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.239 _refine_diff_density_min -0.261 _refine_diff_density_rms 0.057 # Attachment '14d.CIF' data_14d _database_code_depnum_ccdc_archive 'CCDC 604745' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H26 N2 O2' _chemical_formula_weight 386.48 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 11.448(2) _cell_length_b 11.905(2) _cell_length_c 15.067(3) _cell_angle_alpha 86.50(3) _cell_angle_beta 87.96(3) _cell_angle_gamma 77.45(3) _cell_volume 2000.1(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7689 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.283 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9887 _exptl_absorpt_correction_T_max 0.9903 _exptl_absorpt_process_details 'SORTAV (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD Area Detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number none _diffrn_standards_decay_% negligible _diffrn_reflns_number 17728 _diffrn_reflns_av_R_equivalents 0.1722 _diffrn_reflns_av_sigmaI/netI 0.3207 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 27.48 _reflns_number_total 7744 _reflns_number_gt 2276 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO, COLLECT' _computing_data_reduction 'DENZO, COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.0000P)^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 SHELXL _refine_ls_extinction_coef 0.0014(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 7744 _refine_ls_number_parameters 526 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2781 _refine_ls_R_factor_gt 0.0682 _refine_ls_wR_factor_ref 0.1613 _refine_ls_wR_factor_gt 0.1036 _refine_ls_goodness_of_fit_ref 0.867 _refine_ls_restrained_S_all 0.867 _refine_ls_shift/su_max 0.028 _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 C1 C 0.1648(4) 0.1021(4) 0.3998(3) 0.0312(14) Uani 1 1 d . . . H1A H 0.2321 0.1261 0.4273 0.037 Uiso 1 1 calc R . . H1B H 0.1861 0.0173 0.3959 0.037 Uiso 1 1 calc R . . C2 C 0.0527(4) 0.1346(4) 0.4583(3) 0.0319(14) Uani 1 1 d . . . H2A H 0.0750 0.1178 0.5214 0.038 Uiso 1 1 calc R . . H2B H -0.0036 0.0858 0.4450 0.038 Uiso 1 1 calc R . . C3 C -0.0114(4) 0.2614(4) 0.4458(3) 0.0311(14) Uani 1 1 d . . . H3A H -0.0804 0.2780 0.4881 0.037 Uiso 1 1 calc R . . H3B H 0.0441 0.3115 0.4582 0.037 Uiso 1 1 calc R . . C4 C -0.0544(4) 0.2865(4) 0.3514(3) 0.0260(13) Uani 1 1 d . . . H4 H -0.1156 0.2399 0.3427 0.031 Uiso 1 1 calc R . . C5 C 0.0499(4) 0.2445(4) 0.2910(4) 0.0277(14) Uani 1 1 d . . . C6 C 0.1464(4) 0.1579(4) 0.3087(4) 0.0286(14) Uani 1 1 d . . . C7 C 0.2174(4) 0.1461(4) 0.2292(4) 0.0279(14) Uani 1 1 d . . . C8 C 0.3327(4) 0.0636(5) 0.2214(4) 0.0306(14) Uani 1 1 d . . . C9 C 0.5050(4) -0.0028(4) 0.1344(3) 0.0410(15) Uani 1 1 d . . . H9A H 0.5583 0.0120 0.1797 0.061 Uiso 1 1 calc R . . H9B H 0.5395 0.0099 0.0751 0.061 Uiso 1 1 calc R . . H9C H 0.4956 -0.0827 0.1423 0.061 Uiso 1 1 calc R . . C10 C 0.1607(4) 0.2275(4) 0.1654(4) 0.0270(14) Uani 1 1 d . . . C11 C 0.1922(4) 0.2543(4) 0.0713(3) 0.0249(13) Uani 1 1 d . . . C12 C 0.2016(4) 0.1714(4) 0.0093(3) 0.0357(13) Uani 1 1 d . . . H12 H 0.1869 0.0977 0.0274 0.043 Uiso 1 1 calc R . . C13 C 0.2318(4) 0.1944(5) -0.0781(3) 0.0431(15) Uani 1 1 d . . . H13 H 0.2379 0.1366 -0.1198 0.052 Uiso 1 1 calc R . . C14 C 0.2537(4) 0.3017(5) -0.1059(4) 0.0459(16) Uani 1 1 d . . . H14 H 0.2745 0.3175 -0.1663 0.055 Uiso 1 1 calc R . . C15 C 0.2447(4) 0.3842(5) -0.0450(3) 0.0415(14) Uani 1 1 d . . . H15 H 0.2602 0.4574 -0.0631 0.050 Uiso 1 1 calc R . . C16 C 0.2128(3) 0.3613(4) 0.0435(3) 0.0331(13) Uani 1 1 d . . . H16 H 0.2052 0.4197 0.0849 0.040 Uiso 1 1 calc R . . C17 C -0.0200(4) 0.3967(4) 0.1754(3) 0.0294(14) Uani 1 1 d . . . H17A H -0.0396 0.3939 0.1122 0.035 Uiso 1 1 calc R . . H17B H 0.0212 0.4610 0.1805 0.035 Uiso 1 1 calc R . . C18 C -0.1329(4) 0.4165(4) 0.2316(3) 0.0305(14) Uani 1 1 d . . . H18A H -0.1820 0.4939 0.2156 0.037 Uiso 1 1 calc R . . H18B H -0.1798 0.3588 0.2188 0.037 Uiso 1 1 calc R . . C19 C -0.2224(4) 0.4452(4) 0.3777(3) 0.0309(14) Uani 1 1 d . . . H19A H -0.2075 0.4284 0.4420 0.037 Uiso 1 1 calc R . . H19B H -0.2809 0.4007 0.3605 0.037 Uiso 1 1 calc R . . C20 C -0.2738(4) 0.5713(4) 0.3611(3) 0.0253(13) Uani 1 1 d . . . C21 C -0.2071(4) 0.6515(4) 0.3783(3) 0.0307(14) Uani 1 1 d . . . H21 H -0.1285 0.6256 0.4002 0.037 Uiso 1 1 calc R . . C22 C -0.2529(4) 0.7680(4) 0.3641(3) 0.0360(15) Uani 1 1 d . . . H22 H -0.2059 0.8216 0.3767 0.043 Uiso 1 1 calc R . . C23 C -0.3674(4) 0.8076(4) 0.3315(3) 0.0347(15) Uani 1 1 d . . . H23 H -0.3986 0.8879 0.3214 0.042 Uiso 1 1 calc R . . C24 C -0.4351(4) 0.7296(5) 0.3142(3) 0.0331(15) Uani 1 1 d . . . H24 H -0.5136 0.7560 0.2921 0.040 Uiso 1 1 calc R . . C25 C -0.3888(4) 0.6116(4) 0.3288(3) 0.0318(14) Uani 1 1 d . . . H25 H -0.4362 0.5583 0.3166 0.038 Uiso 1 1 calc R . . C26 C -0.3200(4) 1.1013(4) 0.4023(3) 0.0290(14) Uani 1 1 d . . . H26A H -0.2559 1.1314 0.4290 0.035 Uiso 1 1 calc R . . H26B H -0.2928 1.0167 0.3999 0.035 Uiso 1 1 calc R . . C27 C -0.4343(4) 1.1294(4) 0.4598(4) 0.0355(15) Uani 1 1 d . . . H27A H -0.4876 1.0781 0.4454 0.043 Uiso 1 1 calc R . . H27B H -0.4131 1.1131 0.5231 0.043 Uiso 1 1 calc R . . C28 C -0.5017(4) 1.2536(4) 0.4471(3) 0.0307(14) Uani 1 1 d . . . H28A H -0.4482 1.3058 0.4588 0.037 Uiso 1 1 calc R . . H28B H -0.5703 1.2683 0.4899 0.037 Uiso 1 1 calc R . . C29 C -0.5470(4) 1.2779(4) 0.3527(3) 0.0278(14) Uani 1 1 d . . . H29 H -0.6084 1.2313 0.3447 0.033 Uiso 1 1 calc R . . C30 C -0.4427(4) 1.2358(4) 0.2920(4) 0.0254(14) Uani 1 1 d . . . C31 C -0.3427(4) 1.1542(4) 0.3103(4) 0.0252(13) Uani 1 1 d . . . C32 C -0.2737(4) 1.1420(4) 0.2302(3) 0.0256(13) Uani 1 1 d . . . C33 C -0.1604(5) 1.0564(5) 0.2230(4) 0.0326(15) Uani 1 1 d . . . C34 C 0.0008(4) 0.9652(4) 0.1329(4) 0.0497(17) Uani 1 1 d . . . H34A H 0.0603 0.9946 0.1646 0.075 Uiso 1 1 calc R . . H34B H 0.0255 0.9582 0.0702 0.075 Uiso 1 1 calc R . . H34C H -0.0053 0.8894 0.1595 0.075 Uiso 1 1 calc R . . C35 C -0.3345(4) 1.2167(4) 0.1632(4) 0.0293(14) Uani 1 1 d . . . C36 C -0.3118(4) 1.2408(4) 0.0680(4) 0.0308(14) Uani 1 1 d . . . C37 C -0.4002(4) 1.2456(4) 0.0056(3) 0.0414(14) Uani 1 1 d . . . H37 H -0.4755 1.2305 0.0248 0.050 Uiso 1 1 calc R . . C38 C -0.3805(5) 1.2716(4) -0.0831(4) 0.0501(16) Uani 1 1 d . . . H38 H -0.4422 1.2755 -0.1244 0.060 Uiso 1 1 calc R . . C39 C -0.2704(5) 1.2921(5) -0.1120(4) 0.0572(18) Uani 1 1 d . . . H39 H -0.2563 1.3099 -0.1732 0.069 Uiso 1 1 calc R . . C40 C -0.1825(5) 1.2869(4) -0.0524(4) 0.0497(16) Uani 1 1 d . . . H40 H -0.1072 1.3012 -0.0725 0.060 Uiso 1 1 calc R . . C41 C -0.2017(4) 1.2607(4) 0.0376(3) 0.0370(14) Uani 1 1 d . . . H41 H -0.1392 1.2565 0.0783 0.044 Uiso 1 1 calc R . . C42 C -0.5170(4) 1.3842(4) 0.1741(3) 0.0325(14) Uani 1 1 d . . . H42A H -0.5388 1.3826 0.1113 0.039 Uiso 1 1 calc R . . H42B H -0.4731 1.4466 0.1787 0.039 Uiso 1 1 calc R . . C43 C -0.6289(4) 1.4065(4) 0.2326(3) 0.0300(14) Uani 1 1 d . . . H43A H -0.6773 1.4842 0.2166 0.036 Uiso 1 1 calc R . . H43B H -0.6774 1.3494 0.2217 0.036 Uiso 1 1 calc R . . C44 C -0.7124(4) 1.4364(4) 0.3797(3) 0.0303(14) Uani 1 1 d . . . H44A H -0.6959 1.4214 0.4439 0.036 Uiso 1 1 calc R . . H44B H -0.7703 1.3901 0.3645 0.036 Uiso 1 1 calc R . . C45 C -0.7676(4) 1.5613(4) 0.3626(3) 0.0271(14) Uani 1 1 d . . . C46 C -0.7049(4) 1.6455(4) 0.3806(3) 0.0307(14) Uani 1 1 d . . . H46 H -0.6272 1.6223 0.4046 0.037 Uiso 1 1 calc R . . C47 C -0.7528(4) 1.7610(4) 0.3646(3) 0.0336(15) Uani 1 1 d . . . H47 H -0.7075 1.8163 0.3764 0.040 Uiso 1 1 calc R . . C48 C -0.8671(4) 1.7972(4) 0.3310(3) 0.0309(14) Uani 1 1 d . . . H48 H -0.9011 1.8770 0.3208 0.037 Uiso 1 1 calc R . . C49 C -0.9308(4) 1.7148(5) 0.3128(3) 0.0325(15) Uani 1 1 d . . . H49 H -1.0088 1.7382 0.2893 0.039 Uiso 1 1 calc R . . C50 C -0.8820(4) 1.5996(5) 0.3286(3) 0.0338(15) Uani 1 1 d . . . H50 H -0.9273 1.5446 0.3160 0.041 Uiso 1 1 calc R . . N1 N 0.0582(3) 0.2883(3) 0.2053(3) 0.0285(11) Uani 1 1 d . . . N2 N -0.1087(3) 0.4082(3) 0.3265(3) 0.0258(11) Uani 1 1 d . . . N3 N -0.4400(3) 1.2722(3) 0.2031(3) 0.0265(11) Uani 1 1 d . . . N4 N -0.6002(3) 1.3989(3) 0.3281(3) 0.0282(11) Uani 1 1 d . . . O1 O 0.3748(3) -0.0048(3) 0.2802(3) 0.0464(11) Uani 1 1 d . . . O2 O 0.3889(3) 0.0749(3) 0.1433(2) 0.0377(10) Uani 1 1 d . . . O3 O -0.1103(3) 1.0019(3) 0.2862(3) 0.0438(11) Uani 1 1 d . . . O4 O -0.1141(3) 1.0440(3) 0.1396(2) 0.0421(11) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.033(3) 0.026(3) 0.032(4) 0.004(3) 0.002(3) -0.003(2) C2 0.042(3) 0.034(4) 0.017(4) 0.004(3) 0.000(3) -0.003(3) C3 0.039(3) 0.031(4) 0.021(4) -0.005(3) 0.001(3) -0.001(3) C4 0.032(3) 0.026(3) 0.018(4) 0.000(3) 0.001(3) -0.004(3) C5 0.034(3) 0.022(3) 0.027(4) 0.004(3) -0.002(3) -0.007(3) C6 0.033(3) 0.025(4) 0.027(4) 0.004(3) -0.005(3) -0.005(3) C7 0.030(3) 0.026(4) 0.029(4) -0.002(3) -0.001(3) -0.008(3) C8 0.035(3) 0.033(4) 0.026(4) -0.006(3) -0.004(3) -0.010(3) C9 0.034(3) 0.045(4) 0.038(4) -0.001(3) 0.008(3) 0.004(3) C10 0.032(3) 0.024(4) 0.025(4) -0.003(3) 0.003(3) -0.005(3) C11 0.031(3) 0.032(4) 0.013(4) 0.002(3) -0.003(2) -0.010(3) C12 0.039(3) 0.038(4) 0.028(4) 0.000(3) 0.004(2) -0.006(3) C13 0.050(3) 0.044(4) 0.029(4) -0.001(3) 0.000(3) 0.001(3) C14 0.050(4) 0.055(4) 0.025(4) 0.007(4) 0.008(3) 0.004(3) C15 0.047(3) 0.045(4) 0.028(4) 0.009(3) 0.010(3) -0.004(3) C16 0.028(3) 0.037(4) 0.030(4) -0.005(3) 0.002(2) 0.002(2) C17 0.031(3) 0.034(4) 0.020(4) 0.003(3) -0.001(3) -0.002(3) C18 0.035(3) 0.028(4) 0.025(4) -0.003(3) 0.001(3) 0.004(3) C19 0.032(3) 0.026(3) 0.031(4) 0.003(3) 0.013(3) 0.000(3) C20 0.028(3) 0.028(3) 0.018(4) -0.001(3) 0.009(2) -0.003(3) C21 0.026(3) 0.033(4) 0.031(4) -0.003(3) 0.001(3) -0.001(3) C22 0.034(3) 0.041(4) 0.034(4) -0.005(3) 0.001(3) -0.010(3) C23 0.036(3) 0.032(4) 0.030(4) 0.004(3) 0.007(3) 0.002(3) C24 0.029(3) 0.042(4) 0.024(4) 0.005(3) -0.001(3) 0.000(3) C25 0.030(3) 0.039(4) 0.026(4) -0.003(3) 0.002(3) -0.008(3) C26 0.033(3) 0.030(3) 0.023(4) 0.005(3) -0.005(3) -0.004(2) C27 0.039(3) 0.037(4) 0.031(4) 0.007(3) -0.008(3) -0.011(3) C28 0.033(3) 0.035(4) 0.023(4) 0.003(3) 0.005(3) -0.006(3) C29 0.032(3) 0.025(3) 0.027(4) -0.002(3) 0.002(3) -0.008(3) C30 0.032(3) 0.032(4) 0.013(4) -0.003(3) 0.000(3) -0.008(3) C31 0.028(3) 0.025(3) 0.022(4) -0.001(3) 0.000(3) -0.006(3) C32 0.028(3) 0.027(3) 0.020(4) -0.006(3) 0.002(3) -0.002(3) C33 0.040(4) 0.035(4) 0.025(4) 0.000(3) 0.009(3) -0.013(3) C34 0.038(3) 0.050(4) 0.049(5) 0.002(3) 0.008(3) 0.014(3) C35 0.035(3) 0.027(4) 0.026(4) -0.007(3) 0.006(3) -0.005(3) C36 0.036(3) 0.030(4) 0.022(4) 0.000(3) 0.008(3) 0.000(3) C37 0.052(3) 0.040(4) 0.030(4) 0.002(3) 0.000(3) -0.008(3) C38 0.071(4) 0.041(4) 0.031(4) -0.001(3) -0.005(3) 0.004(3) C39 0.089(5) 0.049(5) 0.025(4) 0.001(3) 0.014(4) 0.000(4) C40 0.066(4) 0.035(4) 0.044(4) -0.002(3) 0.025(3) -0.004(3) C41 0.045(3) 0.035(4) 0.029(4) -0.001(3) 0.008(3) -0.007(3) C42 0.038(3) 0.028(3) 0.030(4) -0.003(3) 0.002(3) -0.003(3) C43 0.035(3) 0.030(4) 0.022(4) 0.000(3) -0.001(3) -0.001(3) C44 0.037(3) 0.031(4) 0.023(4) -0.003(3) 0.003(3) -0.007(3) C45 0.028(3) 0.028(4) 0.023(4) 0.000(3) 0.008(3) -0.004(3) C46 0.026(3) 0.037(4) 0.029(4) -0.001(3) -0.001(3) -0.005(3) C47 0.035(3) 0.033(4) 0.034(4) -0.008(3) 0.006(3) -0.009(3) C48 0.036(3) 0.028(4) 0.025(4) -0.003(3) 0.008(3) 0.000(3) C49 0.031(3) 0.043(4) 0.022(4) -0.003(3) 0.002(3) -0.005(3) C50 0.028(3) 0.045(4) 0.030(4) -0.002(3) 0.001(3) -0.011(3) N1 0.029(2) 0.029(3) 0.022(3) 0.004(2) 0.002(2) 0.002(2) N2 0.033(2) 0.024(3) 0.017(3) 0.002(2) 0.000(2) 0.000(2) N3 0.029(2) 0.024(3) 0.024(3) -0.001(2) -0.003(2) 0.000(2) N4 0.034(2) 0.030(3) 0.017(3) -0.001(2) 0.007(2) -0.002(2) O1 0.045(2) 0.046(3) 0.038(3) 0.014(2) 0.004(2) 0.0090(19) O2 0.033(2) 0.045(3) 0.027(3) 0.0032(19) 0.0052(18) 0.0057(18) O3 0.043(2) 0.047(3) 0.032(3) 0.008(2) -0.002(2) 0.0067(19) O4 0.040(2) 0.044(3) 0.033(3) 0.003(2) -0.0001(19) 0.0094(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 C1 C6 1.490(7) . ? C1 C2 1.522(6) . ? C2 C3 1.532(6) . ? C3 C4 1.514(6) . ? C4 N2 1.478(5) . ? C4 C5 1.491(6) . ? C5 C6 1.360(6) . ? C5 N1 1.371(6) . ? C6 C7 1.420(7) . ? C7 C10 1.394(6) . ? C7 C8 1.470(6) . ? C8 O1 1.205(6) . ? C8 O2 1.335(6) . ? C9 O2 1.452(5) . ? C10 N1 1.377(6) . ? C10 C11 1.484(7) . ? C11 C16 1.383(6) . ? C11 C12 1.384(6) . ? C12 C13 1.376(6) . ? C13 C14 1.391(6) . ? C14 C15 1.370(6) . ? C15 C16 1.396(6) . ? C17 N1 1.458(5) . ? C17 C18 1.503(6) . ? C18 N2 1.460(6) . ? C19 N2 1.484(5) . ? C19 C20 1.498(6) . ? C20 C21 1.386(6) . ? C20 C25 1.394(6) . ? C21 C22 1.379(6) . ? C22 C23 1.389(5) . ? C23 C24 1.374(6) . ? C24 C25 1.396(6) . ? C26 C31 1.495(6) . ? C26 C27 1.529(6) . ? C27 C28 1.516(6) . ? C28 C29 1.521(6) . ? C29 N4 1.467(6) . ? C29 C30 1.494(6) . ? C30 C31 1.356(6) . ? C30 N3 1.383(6) . ? C31 C32 1.416(7) . ? C32 C35 1.402(7) . ? C32 C33 1.470(6) . ? C33 O3 1.207(6) . ? C33 O4 1.351(6) . ? C34 O4 1.444(5) . ? C35 N3 1.380(6) . ? C35 C36 1.471(7) . ? C36 C41 1.390(6) . ? C36 C37 1.395(6) . ? C37 C38 1.375(7) . ? C38 C39 1.385(6) . ? C39 C40 1.361(7) . ? C40 C41 1.394(7) . ? C42 N3 1.480(5) . ? C42 C43 1.513(6) . ? C43 N4 1.480(6) . ? C44 N4 1.475(5) . ? C44 C45 1.494(6) . ? C45 C50 1.395(6) . ? C45 C46 1.398(6) . ? C46 C47 1.376(6) . ? C47 C48 1.389(6) . ? C48 C49 1.389(5) . ? C49 C50 1.373(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 111.4(4) . . ? C1 C2 C3 113.8(4) . . ? C4 C3 C2 109.5(4) . . ? N2 C4 C5 109.8(4) . . ? N2 C4 C3 116.0(4) . . ? C5 C4 C3 107.3(4) . . ? C6 C5 N1 109.9(5) . . ? C6 C5 C4 127.3(5) . . ? N1 C5 C4 122.8(5) . . ? C5 C6 C7 106.3(5) . . ? C5 C6 C1 120.8(5) . . ? C7 C6 C1 132.8(5) . . ? C10 C7 C6 108.2(4) . . ? C10 C7 C8 128.3(5) . . ? C6 C7 C8 123.5(5) . . ? O1 C8 O2 123.0(5) . . ? O1 C8 C7 123.9(5) . . ? O2 C8 C7 113.1(5) . . ? N1 C10 C7 106.8(5) . . ? N1 C10 C11 121.0(5) . . ? C7 C10 C11 132.2(5) . . ? C16 C11 C12 118.7(5) . . ? C16 C11 C10 121.2(5) . . ? C12 C11 C10 120.0(5) . . ? C13 C12 C11 120.8(5) . . ? C12 C13 C14 120.6(5) . . ? C15 C14 C13 119.0(6) . . ? C14 C15 C16 120.5(5) . . ? C11 C16 C15 120.4(5) . . ? N1 C17 C18 109.3(4) . . ? N2 C18 C17 112.2(4) . . ? N2 C19 C20 111.4(4) . . ? C21 C20 C25 118.2(5) . . ? C21 C20 C19 120.1(4) . . ? C25 C20 C19 121.7(4) . . ? C22 C21 C20 121.1(4) . . ? C21 C22 C23 120.4(5) . . ? C24 C23 C22 119.4(5) . . ? C23 C24 C25 120.2(4) . . ? C20 C25 C24 120.7(5) . . ? C31 C26 C27 110.1(4) . . ? C28 C27 C26 113.4(4) . . ? C27 C28 C29 110.2(4) . . ? N4 C29 C30 109.6(4) . . ? N4 C29 C28 115.6(4) . . ? C30 C29 C28 106.7(4) . . ? C31 C30 N3 109.3(5) . . ? C31 C30 C29 127.9(5) . . ? N3 C30 C29 122.6(5) . . ? C30 C31 C32 106.2(5) . . ? C30 C31 C26 121.1(5) . . ? C32 C31 C26 132.6(5) . . ? C35 C32 C31 109.4(4) . . ? C35 C32 C33 128.5(5) . . ? C31 C32 C33 122.0(5) . . ? O3 C33 O4 121.6(5) . . ? O3 C33 C32 123.5(5) . . ? O4 C33 C32 114.8(5) . . ? N3 C35 C32 105.2(5) . . ? N3 C35 C36 119.7(5) . . ? C32 C35 C36 135.0(5) . . ? C41 C36 C37 117.9(5) . . ? C41 C36 C35 120.8(5) . . ? C37 C36 C35 121.2(5) . . ? C38 C37 C36 121.4(5) . . ? C37 C38 C39 119.8(5) . . ? C40 C39 C38 119.8(6) . . ? C39 C40 C41 120.8(5) . . ? C36 C41 C40 120.2(5) . . ? N3 C42 C43 109.1(4) . . ? N4 C43 C42 111.8(4) . . ? N4 C44 C45 112.9(4) . . ? C50 C45 C46 117.1(5) . . ? C50 C45 C44 122.5(5) . . ? C46 C45 C44 120.4(4) . . ? C47 C46 C45 121.7(4) . . ? C46 C47 C48 120.2(5) . . ? C47 C48 C49 118.8(5) . . ? C50 C49 C48 120.5(5) . . ? C49 C50 C45 121.6(5) . . ? C5 N1 C10 108.8(4) . . ? C5 N1 C17 120.6(4) . . ? C10 N1 C17 129.3(5) . . ? C18 N2 C4 107.7(4) . . ? C18 N2 C19 109.6(4) . . ? C4 N2 C19 109.9(4) . . ? C35 N3 C30 109.8(4) . . ? C35 N3 C42 127.3(5) . . ? C30 N3 C42 118.6(4) . . ? C29 N4 C44 109.9(4) . . ? C29 N4 C43 107.5(4) . . ? C44 N4 C43 108.5(4) . . ? C8 O2 C9 114.5(4) . . ? C33 O4 C34 115.0(4) . . ? _diffrn_measured_fraction_theta_max 0.844 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.844 _refine_diff_density_max 0.237 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.056