# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_tompkin_jul_july2012 _database_code_depnum_ccdc_archive 'CCDC 908491' #TrackingRef 'twofiles.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H24 N4 O2' _chemical_formula_weight 316.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0181 0.0091 '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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 8.5300(3) _cell_length_b 12.4076(4) _cell_length_c 15.1863(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1607.27(11) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 5746 _cell_measurement_theta_min 4.5982 _cell_measurement_theta_max 73.2778 _exptl_crystal_description 'flattened prism' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.308 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.708 _exptl_absorpt_correction_T_min 0.85183 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.34.46 (release 25-11-2010 CrysAlis171 .NET) (compiled Nov 25 2010,17:55:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini S' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7943 _diffrn_reflns_av_R_equivalents 0.0204 _diffrn_reflns_av_sigmaI/netI 0.0185 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 10 _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 4.60 _diffrn_reflns_theta_max 73.43 _reflns_number_total 3080 _reflns_number_gt 2966 _reflns_threshold_expression I>2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0534P)^2^+0.8584P] 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 -0.1(3) _refine_ls_number_reflns 3080 _refine_ls_number_parameters 211 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0444 _refine_ls_R_factor_gt 0.0387 _refine_ls_wR_factor_ref 0.1165 _refine_ls_wR_factor_gt 0.1035 _refine_ls_goodness_of_fit_ref 1.154 _refine_ls_restrained_S_all 1.154 _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 0.45272(18) 0.58050(12) 0.73812(11) 0.0314(4) Uani 1 1 d . . . O2 O 0.3644(2) 0.71552(12) 0.50402(10) 0.0305(4) Uani 1 1 d . . . N1 N 0.4478(2) 0.76005(14) 0.71568(12) 0.0245(4) Uani 1 1 d . . . N2 N 0.0913(2) 0.71378(13) 0.74073(12) 0.0237(4) Uani 1 1 d . . . N3 N 0.2179(2) 0.87417(13) 0.67748(12) 0.0224(4) Uani 1 1 d . . . N4 N 0.1826(2) 0.64602(13) 0.59618(12) 0.0230(4) Uani 1 1 d . . . C1 C 0.3833(2) 0.66699(17) 0.74592(14) 0.0238(4) Uani 1 1 d . . . C2 C 0.3687(3) 0.86578(16) 0.71932(15) 0.0259(5) Uani 1 1 d . . . H2A H 0.3560 0.8858 0.7820 0.031 Uiso 1 1 calc R . . H2B H 0.4390 0.9198 0.6922 0.031 Uiso 1 1 calc R . . C3 C 0.0915(3) 0.83003(16) 0.73003(15) 0.0256(5) Uani 1 1 d . . . H3A H -0.0092 0.8516 0.7028 0.031 Uiso 1 1 calc R . . H3B H 0.0959 0.8634 0.7892 0.031 Uiso 1 1 calc R . . C4 C 0.2231(3) 0.67247(16) 0.79332(14) 0.0247(4) Uani 1 1 d . . . H4 H 0.2362 0.7226 0.8444 0.030 Uiso 1 1 calc R . . C5 C 0.6009(3) 0.7546(2) 0.67284(18) 0.0358(5) Uani 1 1 d . . . H5A H 0.5875 0.7328 0.6113 0.054 Uiso 1 1 calc R . . H5B H 0.6668 0.7017 0.7033 0.054 Uiso 1 1 calc R . . H5C H 0.6512 0.8255 0.6752 0.054 Uiso 1 1 calc R . . C6 C 0.1836(3) 0.56185(17) 0.83146(16) 0.0311(5) Uani 1 1 d . . . H6A H 0.1828 0.5082 0.7841 0.047 Uiso 1 1 calc R . . H6B H 0.0800 0.5644 0.8593 0.047 Uiso 1 1 calc R . . H6C H 0.2625 0.5419 0.8754 0.047 Uiso 1 1 calc R . . C7 C 0.0547(2) 0.65788(16) 0.66091(15) 0.0245(4) Uani 1 1 d . . . H7A H -0.0331 0.6960 0.6319 0.029 Uiso 1 1 calc R . . H7B H 0.0168 0.5849 0.6766 0.029 Uiso 1 1 calc R . . C8 C 0.2603(2) 0.72993(16) 0.55813(13) 0.0221(4) Uani 1 1 d . . . C9 C 0.2084(2) 0.84608(15) 0.58372(13) 0.0205(4) Uani 1 1 d . . . H9 H 0.0956 0.8528 0.5666 0.025 Uiso 1 1 calc R . . C10 C 0.2236(3) 0.53589(17) 0.57002(16) 0.0304(5) Uani 1 1 d . . . H10A H 0.3078 0.5381 0.5262 0.046 Uiso 1 1 calc R . . H10B H 0.1314 0.5005 0.5446 0.046 Uiso 1 1 calc R . . H10C H 0.2590 0.4955 0.6218 0.046 Uiso 1 1 calc R . . C11 C 0.2991(2) 0.92800(16) 0.52754(15) 0.0242(4) Uani 1 1 d . . . H11A H 0.4075 0.9341 0.5503 0.029 Uiso 1 1 calc R . . H11B H 0.3049 0.9014 0.4662 0.029 Uiso 1 1 calc R . . C12 C 0.2237(2) 1.03794(16) 0.52797(14) 0.0233(4) Uani 1 1 d . . . C13 C 0.2525(3) 1.11337(17) 0.59364(15) 0.0264(5) Uani 1 1 d . . . H13 H 0.3250 1.0971 0.6392 0.032 Uiso 1 1 calc R . . C14 C 0.1761(3) 1.21284(17) 0.59327(16) 0.0295(5) Uani 1 1 d . . . H14 H 0.1962 1.2635 0.6388 0.035 Uiso 1 1 calc R . . C15 C 0.0709(3) 1.23792(17) 0.52688(16) 0.0310(5) Uani 1 1 d . . . H15 H 0.0187 1.3055 0.5269 0.037 Uiso 1 1 calc R . . C16 C 0.0424(3) 1.16387(18) 0.46048(16) 0.0303(5) Uani 1 1 d . . . H16 H -0.0286 1.1810 0.4144 0.036 Uiso 1 1 calc R . . C17 C 0.1178(3) 1.06428(17) 0.46128(15) 0.0262(4) Uani 1 1 d . . . H17 H 0.0969 1.0136 0.4159 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 0.0268(8) 0.0268(8) 0.0405(10) 0.0048(7) -0.0025(7) 0.0062(6) O2 0.0333(8) 0.0277(7) 0.0303(9) -0.0011(6) 0.0075(6) 0.0059(6) N1 0.0239(9) 0.0243(8) 0.0254(9) 0.0013(7) -0.0034(7) -0.0020(7) N2 0.0249(9) 0.0190(8) 0.0272(10) 0.0012(7) 0.0027(7) 0.0014(7) N3 0.0275(9) 0.0174(7) 0.0223(9) -0.0009(6) 0.0022(7) -0.0007(7) N4 0.0261(9) 0.0187(8) 0.0244(9) -0.0019(7) -0.0021(7) 0.0023(7) C1 0.0246(10) 0.0244(10) 0.0224(10) 0.0025(8) -0.0071(8) -0.0006(8) C2 0.0351(12) 0.0193(9) 0.0234(10) -0.0005(8) -0.0030(9) -0.0044(9) C3 0.0310(12) 0.0209(10) 0.0249(11) 0.0018(8) 0.0069(9) 0.0043(8) C4 0.0314(11) 0.0215(10) 0.0213(10) 0.0015(8) 0.0005(8) -0.0002(8) C5 0.0240(11) 0.0410(13) 0.0425(14) 0.0096(11) -0.0019(10) -0.0031(10) C6 0.0358(12) 0.0243(10) 0.0331(12) 0.0090(9) 0.0039(10) 0.0012(9) C7 0.0224(10) 0.0207(9) 0.0305(12) 0.0034(8) -0.0004(8) -0.0011(8) C8 0.0218(10) 0.0224(10) 0.0220(10) 0.0007(8) -0.0055(8) 0.0033(8) C9 0.0208(10) 0.0203(9) 0.0203(10) 0.0014(7) 0.0007(8) 0.0019(8) C10 0.0371(12) 0.0197(10) 0.0344(12) -0.0060(9) -0.0018(10) 0.0018(9) C11 0.0238(10) 0.0236(10) 0.0251(11) 0.0038(8) 0.0027(8) 0.0009(8) C12 0.0233(10) 0.0204(9) 0.0264(11) 0.0063(8) 0.0061(9) -0.0028(8) C13 0.0236(11) 0.0266(10) 0.0291(11) 0.0035(8) 0.0010(9) -0.0046(8) C14 0.0328(12) 0.0223(10) 0.0334(12) -0.0032(9) 0.0053(9) -0.0067(9) C15 0.0349(12) 0.0218(10) 0.0364(13) 0.0048(9) 0.0081(10) 0.0032(9) C16 0.0314(12) 0.0289(11) 0.0307(12) 0.0089(9) 0.0003(9) 0.0021(9) C17 0.0300(11) 0.0230(10) 0.0255(11) 0.0034(8) 0.0031(9) -0.0012(9) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C1 1.231(3) . ? O2 C8 1.223(3) . ? N1 C1 1.359(3) . ? N1 C5 1.461(3) . ? N1 C2 1.477(3) . ? N2 C7 1.431(3) . ? N2 C3 1.451(2) . ? N2 C4 1.471(3) . ? N3 C2 1.438(3) . ? N3 C3 1.449(3) . ? N3 C9 1.468(3) . ? N4 C8 1.363(3) . ? N4 C10 1.465(3) . ? N4 C7 1.475(3) . ? C1 C4 1.546(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C6 1.527(3) . ? C4 H4 1.0000 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.557(3) . ? C9 C11 1.536(3) . ? C9 H9 1.0000 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.508(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.390(3) . ? C12 C17 1.396(3) . ? C13 C14 1.396(3) . ? C13 H13 0.9500 . ? C14 C15 1.385(3) . ? C14 H14 0.9500 . ? C15 C16 1.386(3) . ? C15 H15 0.9500 . ? C16 C17 1.393(3) . ? C16 H16 0.9500 . ? C17 H17 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 C1 N1 C5 118.24(19) . . ? C1 N1 C2 123.85(18) . . ? C5 N1 C2 117.83(18) . . ? C7 N2 C3 112.77(17) . . ? C7 N2 C4 117.22(16) . . ? C3 N2 C4 113.95(17) . . ? C2 N3 C3 113.25(17) . . ? C2 N3 C9 117.42(17) . . ? C3 N3 C9 113.79(17) . . ? C8 N4 C10 118.78(19) . . ? C8 N4 C7 124.45(17) . . ? C10 N4 C7 116.74(17) . . ? O1 C1 N1 120.9(2) . . ? O1 C1 C4 120.54(19) . . ? N1 C1 C4 118.56(18) . . ? N3 C2 N1 117.17(17) . . ? N3 C2 H2A 108.0 . . ? N1 C2 H2A 108.0 . . ? N3 C2 H2B 108.0 . . ? N1 C2 H2B 108.0 . . ? H2A C2 H2B 107.2 . . ? N3 C3 N2 116.00(17) . . ? N3 C3 H3A 108.3 . . ? N2 C3 H3A 108.3 . . ? N3 C3 H3B 108.3 . . ? N2 C3 H3B 108.3 . . ? H3A C3 H3B 107.4 . . ? N2 C4 C6 110.51(18) . . ? N2 C4 C1 115.98(16) . . ? C6 C4 C1 109.40(17) . . ? N2 C4 H4 106.8 . . ? C6 C4 H4 106.8 . . ? C1 C4 H4 106.8 . . ? N1 C5 H5A 109.5 . . ? N1 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N1 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N2 C7 N4 116.85(17) . . ? N2 C7 H7A 108.1 . . ? N4 C7 H7A 108.1 . . ? N2 C7 H7B 108.1 . . ? N4 C7 H7B 108.1 . . ? H7A C7 H7B 107.3 . . ? O2 C8 N4 121.76(19) . . ? O2 C8 C9 120.63(18) . . ? N4 C8 C9 117.59(17) . . ? N3 C9 C11 110.72(16) . . ? N3 C9 C8 116.50(16) . . ? C11 C9 C8 109.31(16) . . ? N3 C9 H9 106.6 . . ? C11 C9 H9 106.6 . . ? C8 C9 H9 106.6 . . ? N4 C10 H10A 109.5 . . ? N4 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N4 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C9 112.43(17) . . ? C12 C11 H11A 109.1 . . ? C9 C11 H11A 109.1 . . ? C12 C11 H11B 109.1 . . ? C9 C11 H11B 109.1 . . ? H11A C11 H11B 107.9 . . ? C13 C12 C17 118.52(19) . . ? C13 C12 C11 122.5(2) . . ? C17 C12 C11 118.98(19) . . ? C12 C13 C14 120.7(2) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? C15 C14 C13 120.3(2) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C14 C15 C16 119.6(2) . . ? C14 C15 H15 120.2 . . ? C16 C15 H15 120.2 . . ? C15 C16 C17 120.0(2) . . ? C15 C16 H16 120.0 . . ? C17 C16 H16 120.0 . . ? C16 C17 C12 120.9(2) . . ? C16 C17 H17 119.6 . . ? C12 C17 H17 119.6 . . ? 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 C5 N1 C1 O1 0.6(3) . . . . ? C2 N1 C1 O1 177.3(2) . . . . ? C5 N1 C1 C4 178.57(19) . . . . ? C2 N1 C1 C4 -4.8(3) . . . . ? C3 N3 C2 N1 79.0(2) . . . . ? C9 N3 C2 N1 -56.8(2) . . . . ? C1 N1 C2 N3 -56.7(3) . . . . ? C5 N1 C2 N3 120.0(2) . . . . ? C2 N3 C3 N2 -69.2(2) . . . . ? C9 N3 C3 N2 68.3(2) . . . . ? C7 N2 C3 N3 -69.4(2) . . . . ? C4 N2 C3 N3 67.4(2) . . . . ? C7 N2 C4 C6 -67.2(2) . . . . ? C3 N2 C4 C6 157.97(18) . . . . ? C7 N2 C4 C1 58.0(2) . . . . ? C3 N2 C4 C1 -76.8(2) . . . . ? O1 C1 C4 N2 -120.8(2) . . . . ? N1 C1 C4 N2 61.3(2) . . . . ? O1 C1 C4 C6 5.0(3) . . . . ? N1 C1 C4 C6 -172.92(19) . . . . ? C3 N2 C7 N4 79.4(2) . . . . ? C4 N2 C7 N4 -55.9(2) . . . . ? C8 N4 C7 N2 -59.6(3) . . . . ? C10 N4 C7 N2 122.4(2) . . . . ? C10 N4 C8 O2 -1.2(3) . . . . ? C7 N4 C8 O2 -179.19(19) . . . . ? C10 N4 C8 C9 176.99(19) . . . . ? C7 N4 C8 C9 -1.0(3) . . . . ? C2 N3 C9 C11 -67.3(2) . . . . ? C3 N3 C9 C11 157.05(16) . . . . ? C2 N3 C9 C8 58.4(2) . . . . ? C3 N3 C9 C8 -77.2(2) . . . . ? O2 C8 C9 N3 -122.9(2) . . . . ? N4 C8 C9 N3 58.9(2) . . . . ? O2 C8 C9 C11 3.5(3) . . . . ? N4 C8 C9 C11 -174.68(17) . . . . ? N3 C9 C11 C12 -67.5(2) . . . . ? C8 C9 C11 C12 162.82(18) . . . . ? C9 C11 C12 C13 84.9(2) . . . . ? C9 C11 C12 C17 -93.3(2) . . . . ? C17 C12 C13 C14 0.6(3) . . . . ? C11 C12 C13 C14 -177.70(19) . . . . ? C12 C13 C14 C15 -0.4(3) . . . . ? C13 C14 C15 C16 -0.3(3) . . . . ? C14 C15 C16 C17 0.8(3) . . . . ? C15 C16 C17 C12 -0.6(3) . . . . ? C13 C12 C17 C16 -0.1(3) . . . . ? C11 C12 C17 C16 178.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 70.00 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.204 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.058 data_tompkin2012 _database_code_depnum_ccdc_archive 'CCDC 908492' #TrackingRef 'twofiles.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H28 N4 O2' _chemical_formula_weight 392.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0181 0.0091 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.0424(7) _cell_length_b 11.6660(4) _cell_length_c 12.3412(5) _cell_angle_alpha 90.00 _cell_angle_beta 111.569(5) _cell_angle_gamma 90.00 _cell_volume 2014.04(14) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 3622 _cell_measurement_theta_min 3.7858 _cell_measurement_theta_max 72.7098 _exptl_crystal_description 'shard cut from large crystal' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.05 __exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.294 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 0.672 _exptl_absorpt_correction_T_min 0.83381 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.34.46 (release 25-11-2010 CrysAlis171 .NET) (compiled Nov 25 2010,17:55:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; Diffraction very streaky. Attempts to refine and/or process data as a twin gave poorer models than this one. ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini S' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8335 _diffrn_reflns_av_R_equivalents 0.0799 _diffrn_reflns_av_sigmaI/netI 0.0551 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 7.38 _diffrn_reflns_theta_max 69.98 _reflns_number_total 3785 _reflns_number_gt 3040 _reflns_threshold_expression I>2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0724P)^2^+3.6761P] 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 3785 _refine_ls_number_parameters 264 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1001 _refine_ls_R_factor_gt 0.0809 _refine_ls_wR_factor_ref 0.2153 _refine_ls_wR_factor_gt 0.2029 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.098 _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 0.75755(17) 0.7627(2) 1.08945(19) 0.0398(6) Uani 1 1 d . . . O2 O 0.66855(17) 1.0911(2) 1.04664(19) 0.0396(6) Uani 1 1 d . . . N1 N 0.7003(2) 0.9974(2) 0.7997(2) 0.0349(6) Uani 1 1 d . . . N2 N 0.86173(19) 0.9290(2) 0.9214(2) 0.0346(6) Uani 1 1 d . . . N3 N 0.6636(2) 0.8533(2) 0.9266(2) 0.0343(6) Uani 1 1 d . . . N4 N 0.81816(19) 1.0484(2) 1.0600(2) 0.0342(6) Uani 1 1 d . . . C1 C 0.7950(2) 0.9646(3) 0.8068(3) 0.0369(7) Uani 1 1 d . . . H1A H 0.8235 1.0302 0.7803 0.044 Uiso 1 1 calc R . . H1B H 0.7885 0.9008 0.7515 0.044 Uiso 1 1 calc R . . C2 C 0.6423(2) 0.9028(3) 0.8087(3) 0.0360(7) Uani 1 1 d . . . H2A H 0.6482 0.8409 0.7570 0.043 Uiso 1 1 calc R . . H2B H 0.5747 0.9281 0.7783 0.043 Uiso 1 1 calc R . . C3 C 0.7495(2) 0.8123(3) 0.9979(3) 0.0342(7) Uani 1 1 d . . . C4 C 0.8407(2) 0.8225(3) 0.9685(3) 0.0344(7) Uani 1 1 d . . . H4 H 0.8946 0.8131 1.0451 0.041 Uiso 1 1 calc R . . C5 C 0.8877(2) 1.0215(3) 1.0059(3) 0.0353(7) Uani 1 1 d . . . H5A H 0.8983 1.0916 0.9669 0.042 Uiso 1 1 calc R . . H5B H 0.9492 1.0017 1.0684 0.042 Uiso 1 1 calc R . . C6 C 0.7270(2) 1.0796(3) 0.9998(3) 0.0331(7) Uani 1 1 d . . . C7 C 0.6984(2) 1.1015(3) 0.8666(3) 0.0344(7) Uani 1 1 d . . . H7 H 0.7467 1.1556 0.8575 0.041 Uiso 1 1 calc R . . C8 C 0.5827(2) 0.8417(3) 0.9647(3) 0.0422(8) Uani 1 1 d . . . H8A H 0.6065 0.8307 1.0494 0.063 Uiso 1 1 calc R . . H8B H 0.5439 0.7755 0.9261 0.063 Uiso 1 1 calc R . . H8C H 0.5435 0.9113 0.9443 0.063 Uiso 1 1 calc R . . C9 C 0.8449(3) 1.0280(3) 1.1863(3) 0.0398(8) Uani 1 1 d . . . H9A H 0.8170 0.9554 1.1983 0.060 Uiso 1 1 calc R . . H9B H 0.8207 1.0908 1.2205 0.060 Uiso 1 1 calc R . . H9C H 0.9147 1.0242 1.2237 0.060 Uiso 1 1 calc R . . C10 C 0.8474(2) 0.7165(3) 0.8974(3) 0.0371(7) Uani 1 1 d . . . H10A H 0.8265 0.6479 0.9288 0.044 Uiso 1 1 calc R . . H10B H 0.8036 0.7265 0.8154 0.044 Uiso 1 1 calc R . . C11 C 0.9477(2) 0.6979(3) 0.9010(3) 0.0351(7) Uani 1 1 d . . . C12 C 0.9740(3) 0.7271(3) 0.8077(3) 0.0386(8) Uani 1 1 d . . . H12 H 0.9287 0.7624 0.7408 0.046 Uiso 1 1 calc R . . C13 C 1.0654(3) 0.7052(3) 0.8113(3) 0.0429(8) Uani 1 1 d . . . H13 H 1.0817 0.7234 0.7459 0.051 Uiso 1 1 calc R . . C14 C 1.1335(3) 0.6569(3) 0.9098(4) 0.0478(9) Uani 1 1 d . . . H14 H 1.1965 0.6429 0.9127 0.057 Uiso 1 1 calc R . . C15 C 1.1083(3) 0.6294(4) 1.0033(3) 0.0513(10) Uani 1 1 d . . . H15 H 1.1545 0.5972 1.0714 0.062 Uiso 1 1 calc R . . C16 C 1.0167(3) 0.6484(3) 0.9989(3) 0.0434(8) Uani 1 1 d . . . H16 H 1.0002 0.6274 1.0635 0.052 Uiso 1 1 calc R . . C17 C 0.6015(2) 1.1620(3) 0.8184(3) 0.0365(7) Uani 1 1 d . . . H17A H 0.5748 1.1542 0.7325 0.044 Uiso 1 1 calc R . . H17B H 0.5569 1.1242 0.8494 0.044 Uiso 1 1 calc R . . C18 C 0.6091(2) 1.2876(3) 0.8502(3) 0.0340(7) Uani 1 1 d . . . C19 C 0.6345(2) 1.3667(3) 0.7820(3) 0.0388(8) Uani 1 1 d . . . H19 H 0.6454 1.3409 0.7150 0.047 Uiso 1 1 calc R . . C20 C 0.6442(3) 1.4817(3) 0.8101(3) 0.0454(9) Uani 1 1 d . . . H20 H 0.6608 1.5342 0.7618 0.054 Uiso 1 1 calc R . . C21 C 0.6298(3) 1.5211(3) 0.9081(4) 0.0482(9) Uani 1 1 d . . . H21 H 0.6373 1.6001 0.9280 0.058 Uiso 1 1 calc R . . C22 C 0.6043(3) 1.4437(4) 0.9771(3) 0.0464(9) Uani 1 1 d . . . H22 H 0.5940 1.4700 1.0444 0.056 Uiso 1 1 calc R . . C23 C 0.5937(2) 1.3292(3) 0.9485(3) 0.0393(8) Uani 1 1 d . . . H23 H 0.5757 1.2774 0.9962 0.047 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 0.0484(13) 0.0456(14) 0.0295(11) 0.0048(10) 0.0193(10) -0.0014(11) O2 0.0478(13) 0.0482(14) 0.0290(11) 0.0033(10) 0.0215(10) 0.0040(11) N1 0.0464(15) 0.0359(14) 0.0258(13) -0.0006(11) 0.0172(11) -0.0006(12) N2 0.0426(15) 0.0359(14) 0.0308(13) -0.0016(11) 0.0200(12) -0.0018(12) N3 0.0413(15) 0.0384(15) 0.0275(13) -0.0002(11) 0.0176(11) -0.0027(12) N4 0.0433(15) 0.0381(15) 0.0246(13) -0.0006(11) 0.0166(11) 0.0007(12) C1 0.0508(19) 0.0392(18) 0.0282(16) 0.0019(13) 0.0235(14) -0.0002(15) C2 0.0438(18) 0.0375(18) 0.0263(15) -0.0006(13) 0.0124(13) -0.0025(14) C3 0.0452(18) 0.0325(16) 0.0280(16) -0.0068(13) 0.0171(14) -0.0043(13) C4 0.0407(17) 0.0366(17) 0.0277(15) -0.0015(13) 0.0149(13) -0.0014(13) C5 0.0405(17) 0.0375(17) 0.0323(16) -0.0031(13) 0.0187(13) -0.0022(13) C6 0.0441(17) 0.0323(16) 0.0277(16) 0.0000(12) 0.0187(14) -0.0015(13) C7 0.0444(18) 0.0384(17) 0.0237(15) 0.0009(13) 0.0166(13) -0.0002(14) C8 0.0415(19) 0.049(2) 0.0409(19) 0.0010(16) 0.0212(15) -0.0036(15) C9 0.0504(19) 0.0436(19) 0.0246(16) 0.0001(14) 0.0129(14) 0.0013(15) C10 0.0442(18) 0.0346(17) 0.0339(17) -0.0035(14) 0.0161(14) -0.0016(14) C11 0.0451(18) 0.0308(16) 0.0315(16) -0.0063(13) 0.0166(14) -0.0012(13) C12 0.0457(19) 0.0393(18) 0.0325(17) -0.0033(14) 0.0164(14) -0.0003(14) C13 0.054(2) 0.044(2) 0.0392(19) -0.0046(15) 0.0267(16) -0.0043(16) C14 0.0424(19) 0.049(2) 0.054(2) -0.0106(18) 0.0205(17) 0.0018(16) C15 0.053(2) 0.052(2) 0.042(2) -0.0013(17) 0.0094(17) 0.0095(18) C16 0.056(2) 0.044(2) 0.0323(17) 0.0017(15) 0.0193(16) 0.0047(16) C17 0.0443(18) 0.0453(19) 0.0239(15) 0.0015(13) 0.0170(14) -0.0021(15) C18 0.0328(16) 0.0441(19) 0.0271(15) 0.0048(13) 0.0134(13) 0.0024(13) C19 0.0415(18) 0.050(2) 0.0307(16) 0.0049(14) 0.0197(14) 0.0032(15) C20 0.0458(19) 0.044(2) 0.049(2) 0.0085(16) 0.0204(16) -0.0001(16) C21 0.046(2) 0.040(2) 0.058(2) -0.0064(17) 0.0190(17) 0.0019(16) C22 0.048(2) 0.058(2) 0.0368(18) -0.0049(17) 0.0197(16) 0.0083(17) C23 0.0414(18) 0.048(2) 0.0326(17) 0.0040(15) 0.0185(14) 0.0034(15) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C3 1.235(4) . ? O2 C6 1.224(4) . ? N1 C2 1.436(4) . ? N1 C1 1.446(4) . ? N1 C7 1.474(4) . ? N2 C5 1.451(4) . ? N2 C4 1.455(4) . ? N2 C1 1.462(4) . ? N3 C3 1.355(4) . ? N3 C8 1.463(4) . ? N3 C2 1.486(4) . ? N4 C6 1.348(4) . ? N4 C5 1.467(4) . ? N4 C9 1.479(4) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.548(5) . ? C4 C10 1.541(4) . ? C4 H4 1.0000 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.559(4) . ? C7 C17 1.530(5) . ? C7 H7 1.0000 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.509(5) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.390(5) . ? C11 C16 1.396(5) . ? C12 C13 1.383(5) . ? C12 H12 0.9500 . ? C13 C14 1.389(5) . ? C13 H13 0.9500 . ? C14 C15 1.378(6) . ? C14 H14 0.9500 . ? C15 C16 1.376(5) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C18 1.511(5) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.393(5) . ? C18 C23 1.402(5) . ? C19 C20 1.380(5) . ? C19 H19 0.9500 . ? C20 C21 1.383(5) . ? C20 H20 0.9500 . ? C21 C22 1.388(6) . ? C21 H21 0.9500 . ? C22 C23 1.376(5) . ? C22 H22 0.9500 . ? C23 H23 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 C2 N1 C1 113.9(3) . . ? C2 N1 C7 116.9(3) . . ? C1 N1 C7 113.9(3) . . ? C5 N2 C4 112.9(2) . . ? C5 N2 C1 113.1(3) . . ? C4 N2 C1 117.1(3) . . ? C3 N3 C8 117.7(3) . . ? C3 N3 C2 125.8(3) . . ? C8 N3 C2 116.4(3) . . ? C6 N4 C5 123.9(3) . . ? C6 N4 C9 116.9(3) . . ? C5 N4 C9 118.8(3) . . ? N1 C1 N2 116.4(3) . . ? N1 C1 H1A 108.2 . . ? N2 C1 H1A 108.2 . . ? N1 C1 H1B 108.2 . . ? N2 C1 H1B 108.2 . . ? H1A C1 H1B 107.3 . . ? N1 C2 N3 117.1(3) . . ? N1 C2 H2A 108.0 . . ? N3 C2 H2A 108.0 . . ? N1 C2 H2B 108.0 . . ? N3 C2 H2B 108.0 . . ? H2A C2 H2B 107.3 . . ? O1 C3 N3 120.6(3) . . ? O1 C3 C4 116.9(3) . . ? N3 C3 C4 122.4(3) . . ? N2 C4 C10 112.8(3) . . ? N2 C4 C3 120.1(3) . . ? C10 C4 C3 108.8(3) . . ? N2 C4 H4 104.5 . . ? C10 C4 H4 104.5 . . ? C3 C4 H4 104.5 . . ? N2 C5 N4 116.0(3) . . ? N2 C5 H5A 108.3 . . ? N4 C5 H5A 108.3 . . ? N2 C5 H5B 108.3 . . ? N4 C5 H5B 108.3 . . ? H5A C5 H5B 107.4 . . ? O2 C6 N4 122.1(3) . . ? O2 C6 C7 120.8(3) . . ? N4 C6 C7 117.1(3) . . ? N1 C7 C17 111.9(3) . . ? N1 C7 C6 113.6(3) . . ? C17 C7 C6 109.8(3) . . ? N1 C7 H7 107.0 . . ? C17 C7 H7 107.0 . . ? C6 C7 H7 107.0 . . ? N3 C8 H8A 109.5 . . ? N3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N4 C9 H9A 109.5 . . ? N4 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N4 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C4 111.9(3) . . ? C11 C10 H10A 109.2 . . ? C4 C10 H10A 109.2 . . ? C11 C10 H10B 109.2 . . ? C4 C10 H10B 109.2 . . ? H10A C10 H10B 107.9 . . ? C12 C11 C16 118.1(3) . . ? C12 C11 C10 121.7(3) . . ? C16 C11 C10 120.2(3) . . ? C13 C12 C11 120.7(3) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C12 C13 C14 120.5(3) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? C15 C14 C13 119.0(3) . . ? C15 C14 H14 120.5 . . ? C13 C14 H14 120.5 . . ? C16 C15 C14 120.6(4) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C15 C16 C11 121.0(3) . . ? C15 C16 H16 119.5 . . ? C11 C16 H16 119.5 . . ? C18 C17 C7 112.1(3) . . ? C18 C17 H17A 109.2 . . ? C7 C17 H17A 109.2 . . ? C18 C17 H17B 109.2 . . ? C7 C17 H17B 109.2 . . ? H17A C17 H17B 107.9 . . ? C19 C18 C23 117.6(3) . . ? C19 C18 C17 119.8(3) . . ? C23 C18 C17 122.6(3) . . ? C20 C19 C18 121.3(3) . . ? C20 C19 H19 119.4 . . ? C18 C19 H19 119.4 . . ? C19 C20 C21 120.4(3) . . ? C19 C20 H20 119.8 . . ? C21 C20 H20 119.8 . . ? C20 C21 C22 119.2(4) . . ? C20 C21 H21 120.4 . . ? C22 C21 H21 120.4 . . ? C23 C22 C21 120.4(3) . . ? C23 C22 H22 119.8 . . ? C21 C22 H22 119.8 . . ? C22 C23 C18 121.2(3) . . ? C22 C23 H23 119.4 . . ? C18 C23 H23 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 C2 N1 C1 N2 -72.1(4) . . . . ? C7 N1 C1 N2 65.4(4) . . . . ? C5 N2 C1 N1 -66.5(4) . . . . ? C4 N2 C1 N1 67.4(4) . . . . ? C1 N1 C2 N3 75.8(4) . . . . ? C7 N1 C2 N3 -60.4(4) . . . . ? C3 N3 C2 N1 -55.8(4) . . . . ? C8 N3 C2 N1 128.2(3) . . . . ? C8 N3 C3 O1 3.1(5) . . . . ? C2 N3 C3 O1 -172.9(3) . . . . ? C8 N3 C3 C4 -178.3(3) . . . . ? C2 N3 C3 C4 5.7(5) . . . . ? C5 N2 C4 C10 -160.2(3) . . . . ? C1 N2 C4 C10 65.9(4) . . . . ? C5 N2 C4 C3 69.5(4) . . . . ? C1 N2 C4 C3 -64.4(4) . . . . ? O1 C3 C4 N2 -138.3(3) . . . . ? N3 C3 C4 N2 43.1(4) . . . . ? O1 C3 C4 C10 89.6(3) . . . . ? N3 C3 C4 C10 -89.0(4) . . . . ? C4 N2 C5 N4 -55.8(4) . . . . ? C1 N2 C5 N4 80.1(3) . . . . ? C6 N4 C5 N2 -58.5(4) . . . . ? C9 N4 C5 N2 114.2(3) . . . . ? C5 N4 C6 O2 173.1(3) . . . . ? C9 N4 C6 O2 0.3(5) . . . . ? C5 N4 C6 C7 -7.3(4) . . . . ? C9 N4 C6 C7 179.9(3) . . . . ? C2 N1 C7 C17 -68.5(3) . . . . ? C1 N1 C7 C17 155.4(3) . . . . ? C2 N1 C7 C6 56.7(4) . . . . ? C1 N1 C7 C6 -79.5(3) . . . . ? O2 C6 C7 N1 -113.5(3) . . . . ? N4 C6 C7 N1 66.8(4) . . . . ? O2 C6 C7 C17 12.7(4) . . . . ? N4 C6 C7 C17 -166.9(3) . . . . ? N2 C4 C10 C11 64.2(4) . . . . ? C3 C4 C10 C11 -160.0(3) . . . . ? C4 C10 C11 C12 -103.0(4) . . . . ? C4 C10 C11 C16 78.1(4) . . . . ? C16 C11 C12 C13 1.3(5) . . . . ? C10 C11 C12 C13 -177.6(3) . . . . ? C11 C12 C13 C14 -2.0(5) . . . . ? C12 C13 C14 C15 0.9(6) . . . . ? C13 C14 C15 C16 0.7(6) . . . . ? C14 C15 C16 C11 -1.4(6) . . . . ? C12 C11 C16 C15 0.3(5) . . . . ? C10 C11 C16 C15 179.2(3) . . . . ? N1 C7 C17 C18 -156.6(3) . . . . ? C6 C7 C17 C18 76.2(3) . . . . ? C7 C17 C18 C19 84.3(4) . . . . ? C7 C17 C18 C23 -94.2(4) . . . . ? C23 C18 C19 C20 -0.1(5) . . . . ? C17 C18 C19 C20 -178.5(3) . . . . ? C18 C19 C20 C21 0.8(6) . . . . ? C19 C20 C21 C22 -0.9(6) . . . . ? C20 C21 C22 C23 0.2(6) . . . . ? C21 C22 C23 C18 0.5(5) . . . . ? C19 C18 C23 C22 -0.6(5) . . . . ? C17 C18 C23 C22 177.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 69.98 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.438 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.074 #===END data_nct0909b _database_code_depnum_ccdc_archive 'CCDC 909951' #TrackingRef '12_nct0909b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H28 N4 O2' _chemical_formula_sum 'C23 H28 N4 O2' _chemical_formula_weight 392.49 _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 Tetragonal _symmetry_space_group_name_H-M P43212 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z+1/4' '-x, -y, z+1/2' '-x+1/2, y+1/2, -z+3/4' 'y, x, -z' 'y+1/2, -x+1/2, z+1/4' '-y+1/2, x+1/2, z+3/4' '-y, -x, -z+1/2' _cell_length_a 8.6628(4) _cell_length_b 8.6628(4) _cell_length_c 55.161(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4139.5(3) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4089 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 27.49 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.260 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1680 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9878 _exptl_absorpt_correction_T_max 0.9918 _exptl_absorpt_process_details Denzo/Scalepack _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'CCD scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12695 _diffrn_reflns_av_R_equivalents 0.0798 _diffrn_reflns_av_sigmaI/netI 0.0602 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -71 _diffrn_reflns_limit_l_max 50 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4561 _reflns_number_gt 4089 _reflns_threshold_expression >2\s(I) _computing_data_collection 'cOLLECT,Nonius BV, 1997-2001' _computing_cell_refinement DENZO/SCALEPACK _computing_data_reduction DENZO/SCALEPACK _computing_structure_solution SHELXs-97 _computing_structure_refinement SHELXL-97 _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^ > 2\s(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^)+(0.0339P)^2^+0.6852P] 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 0.011(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 0.4(12) _refine_ls_number_reflns 4561 _refine_ls_number_parameters 265 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0495 _refine_ls_R_factor_gt 0.0413 _refine_ls_wR_factor_ref 0.1014 _refine_ls_wR_factor_gt 0.0966 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.42952(18) 0.64514(17) 0.94030(2) 0.0269(3) Uani 1 1 d . . . H1 H 0.3165 0.6671 0.9415 0.032 Uiso 1 1 calc R . . C2 C 0.51067(17) 0.80048(18) 0.93424(3) 0.0274(3) Uani 1 1 d . . . C3 C 0.36407(19) 0.81511(19) 0.89491(3) 0.0315(4) Uani 1 1 d . . . H3A H 0.2598 0.8112 0.9022 0.038 Uiso 1 1 calc R . . H3B H 0.3601 0.8907 0.8815 0.038 Uiso 1 1 calc R . . C4 C 0.54955(17) 0.64191(18) 0.87327(2) 0.0271(3) Uani 1 1 d . . . H4 H 0.5575 0.5294 0.8694 0.033 Uiso 1 1 calc R . . C5 C 0.69152(17) 0.68075(17) 0.88914(3) 0.0263(3) Uani 1 1 d . . . C6 C 0.60454(18) 0.47111(17) 0.91744(3) 0.0276(3) Uani 1 1 d . . . H6A H 0.6006 0.3894 0.9049 0.033 Uiso 1 1 calc R . . H6B H 0.6467 0.4238 0.9324 0.033 Uiso 1 1 calc R . . C7 C 0.35560(18) 0.53837(19) 0.90064(3) 0.0299(3) Uani 1 1 d . . . H7A H 0.3610 0.4408 0.8913 0.036 Uiso 1 1 calc R . . H7B H 0.2468 0.5528 0.9056 0.036 Uiso 1 1 calc R . . C8 C 0.5376(2) 1.02732(19) 0.90861(3) 0.0369(4) Uani 1 1 d . . . H8A H 0.5936 1.0628 0.9230 0.055 Uiso 1 1 calc R . . H8B H 0.4547 1.1003 0.9048 0.055 Uiso 1 1 calc R . . H8C H 0.6089 1.0210 0.8948 0.055 Uiso 1 1 calc R . . C9 C 0.85211(17) 0.61860(19) 0.92384(3) 0.0303(3) Uani 1 1 d . . . H9A H 0.8286 0.6944 0.9365 0.045 Uiso 1 1 calc R . . H9B H 0.9352 0.6581 0.9135 0.045 Uiso 1 1 calc R . . H9C H 0.8849 0.5215 0.9314 0.045 Uiso 1 1 calc R . . C10 C 0.48199(19) 0.58695(18) 0.96532(3) 0.0291(3) Uani 1 1 d . . . H10A H 0.4650 0.4741 0.9661 0.035 Uiso 1 1 calc R . . H10B H 0.5942 0.6056 0.9670 0.035 Uiso 1 1 calc R . . C11 C 0.39988(19) 0.66203(19) 0.98643(3) 0.0317(4) Uani 1 1 d . . . C12 C 0.2595(2) 0.6042(3) 0.99433(3) 0.0480(5) Uani 1 1 d . . . H12 H 0.2155 0.5175 0.9864 0.058 Uiso 1 1 calc R . . C13 C 0.1820(2) 0.6717(3) 1.01378(4) 0.0662(7) Uani 1 1 d . . . H13 H 0.0865 0.6301 1.0191 0.079 Uiso 1 1 calc R . . C14 C 0.2441(3) 0.7986(3) 1.02524(4) 0.0657(7) Uani 1 1 d . . . H14 H 0.1904 0.8465 1.0382 0.079 Uiso 1 1 calc R . . C15 C 0.3850(3) 0.8560(2) 1.01769(3) 0.0535(6) Uani 1 1 d . . . H15 H 0.4287 0.9427 1.0257 0.064 Uiso 1 1 calc R . . C16 C 0.4630(2) 0.78758(19) 0.99850(3) 0.0399(4) Uani 1 1 d . . . H16 H 0.5604 0.8271 0.9936 0.048 Uiso 1 1 calc R . . C17 C 0.55901(19) 0.72702(19) 0.84892(3) 0.0298(3) Uani 1 1 d . . . H17A H 0.5239 0.8348 0.8512 0.036 Uiso 1 1 calc R . . H17B H 0.6681 0.7302 0.8436 0.036 Uiso 1 1 calc R . . C18 C 0.46281(18) 0.65260(18) 0.82928(3) 0.0275(3) Uani 1 1 d . . . C19 C 0.34112(19) 0.7293(2) 0.81817(3) 0.0360(4) Uani 1 1 d . . . H19 H 0.3134 0.8297 0.8236 0.043 Uiso 1 1 calc R . . C20 C 0.2590(2) 0.6618(2) 0.79922(3) 0.0415(4) Uani 1 1 d . . . H20 H 0.1755 0.7158 0.7920 0.050 Uiso 1 1 calc R . . C21 C 0.2985(2) 0.5167(2) 0.79100(3) 0.0394(4) Uani 1 1 d . . . H21 H 0.2436 0.4710 0.7779 0.047 Uiso 1 1 calc R . . C22 C 0.4188(2) 0.4386(2) 0.80195(3) 0.0384(4) Uani 1 1 d . . . H22 H 0.4462 0.3384 0.7964 0.046 Uiso 1 1 calc R . . C23 C 0.49978(19) 0.50565(19) 0.82094(3) 0.0333(3) Uani 1 1 d . . . H23 H 0.5818 0.4503 0.8284 0.040 Uiso 1 1 calc R . . N1 N 0.47141(15) 0.87451(15) 0.91330(2) 0.0291(3) Uani 1 1 d . . . N2 N 0.39698(15) 0.66391(15) 0.88456(2) 0.0283(3) Uani 1 1 d . . . N3 N 0.71440(14) 0.59150(15) 0.90917(2) 0.0264(3) Uani 1 1 d . . . N4 N 0.44828(14) 0.52041(15) 0.92238(2) 0.0272(3) Uani 1 1 d . . . O1 O 0.60554(13) 0.85611(13) 0.948222(19) 0.0336(3) Uani 1 1 d . . . O2 O 0.78220(13) 0.78366(12) 0.883542(19) 0.0304(3) 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 0.0289(8) 0.0298(8) 0.0220(7) -0.0006(6) 0.0007(6) -0.0010(6) C2 0.0280(7) 0.0304(8) 0.0237(7) -0.0013(6) 0.0036(6) 0.0023(6) C3 0.0322(8) 0.0369(9) 0.0253(7) 0.0031(7) -0.0010(6) 0.0037(7) C4 0.0309(8) 0.0293(8) 0.0211(7) 0.0003(6) 0.0004(6) -0.0028(6) C5 0.0288(8) 0.0272(8) 0.0228(7) -0.0009(6) 0.0009(6) 0.0004(6) C6 0.0333(8) 0.0252(7) 0.0243(7) -0.0007(6) -0.0002(6) -0.0012(6) C7 0.0301(8) 0.0371(9) 0.0225(7) 0.0020(6) -0.0022(6) -0.0060(6) C8 0.0450(10) 0.0303(9) 0.0354(9) 0.0030(7) 0.0033(7) -0.0010(7) C9 0.0292(8) 0.0337(8) 0.0281(7) -0.0023(6) -0.0048(6) 0.0004(6) C10 0.0351(8) 0.0298(8) 0.0225(7) 0.0015(6) 0.0002(6) 0.0018(6) C11 0.0361(9) 0.0377(9) 0.0214(7) 0.0016(6) -0.0043(7) 0.0074(6) C12 0.0389(10) 0.0763(14) 0.0288(8) -0.0058(9) -0.0002(7) -0.0013(9) C13 0.0415(11) 0.124(2) 0.0330(10) -0.0050(12) 0.0032(9) 0.0128(13) C14 0.0734(16) 0.0972(19) 0.0265(9) -0.0107(11) -0.0038(10) 0.0458(14) C15 0.0910(17) 0.0447(11) 0.0248(8) -0.0037(8) -0.0112(10) 0.0258(11) C16 0.0593(12) 0.0360(9) 0.0243(7) 0.0017(7) -0.0081(8) 0.0052(8) C17 0.0343(8) 0.0308(8) 0.0243(7) 0.0003(6) 0.0009(6) -0.0023(6) C18 0.0312(8) 0.0311(8) 0.0202(6) 0.0036(6) 0.0032(6) -0.0024(6) C19 0.0371(9) 0.0381(9) 0.0329(8) -0.0026(7) 0.0002(7) 0.0072(7) C20 0.0345(9) 0.0518(11) 0.0383(9) 0.0024(8) -0.0092(7) 0.0050(8) C21 0.0434(10) 0.0437(10) 0.0311(8) 0.0002(7) -0.0092(8) -0.0098(8) C22 0.0512(11) 0.0303(9) 0.0338(8) -0.0019(7) -0.0056(8) -0.0013(7) C23 0.0385(9) 0.0321(8) 0.0292(8) 0.0015(7) -0.0058(7) 0.0016(6) N1 0.0330(7) 0.0293(7) 0.0248(6) 0.0018(5) 0.0001(5) 0.0014(5) N2 0.0297(7) 0.0328(7) 0.0225(6) 0.0012(5) -0.0005(5) -0.0028(5) N3 0.0274(6) 0.0282(7) 0.0236(6) -0.0005(5) -0.0014(5) -0.0009(5) N4 0.0287(7) 0.0301(7) 0.0228(6) -0.0016(5) -0.0012(5) -0.0019(5) O1 0.0348(6) 0.0361(6) 0.0299(6) -0.0026(5) -0.0027(5) -0.0029(5) O2 0.0317(6) 0.0314(6) 0.0282(5) 0.0005(5) 0.0005(5) -0.0054(4) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 N4 1.4737(19) . ? C1 C10 1.5381(19) . ? C1 C2 1.555(2) . ? C2 O1 1.2259(18) . ? C2 N1 1.3638(19) . ? C3 N2 1.457(2) . ? C3 N1 1.469(2) . ? C4 N2 1.4733(19) . ? C4 C17 1.535(2) . ? C4 C5 1.547(2) . ? C5 O2 1.2277(18) . ? C5 N3 1.3629(19) . ? C6 N4 1.4454(19) . ? C6 N3 1.4837(19) . ? C7 N2 1.4487(19) . ? C7 N4 1.4512(18) . ? C8 N1 1.466(2) . ? C9 N3 1.4605(19) . ? C10 C11 1.511(2) . ? C11 C12 1.385(3) . ? C11 C16 1.388(2) . ? C12 C13 1.394(3) . ? C13 C14 1.378(4) . ? C14 C15 1.382(4) . ? C15 C16 1.389(3) . ? C17 C18 1.511(2) . ? C18 C19 1.389(2) . ? C18 C23 1.391(2) . ? C19 C20 1.393(2) . ? C20 C21 1.379(3) . ? C21 C22 1.381(2) . ? C22 C23 1.388(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 N4 C1 C10 109.22(12) . . ? N4 C1 C2 116.13(11) . . ? C10 C1 C2 110.07(12) . . ? O1 C2 N1 121.00(15) . . ? O1 C2 C1 120.53(13) . . ? N1 C2 C1 118.46(13) . . ? N2 C3 N1 117.50(13) . . ? N2 C4 C17 110.83(12) . . ? N2 C4 C5 116.50(11) . . ? C17 C4 C5 110.40(12) . . ? O2 C5 N3 121.53(14) . . ? O2 C5 C4 121.62(13) . . ? N3 C5 C4 116.81(13) . . ? N4 C6 N3 116.81(12) . . ? N2 C7 N4 116.73(12) . . ? C11 C10 C1 114.27(12) . . ? C12 C11 C16 118.57(16) . . ? C12 C11 C10 119.99(16) . . ? C16 C11 C10 121.44(16) . . ? C11 C12 C13 120.9(2) . . ? C14 C13 C12 120.0(2) . . ? C13 C14 C15 119.55(19) . . ? C14 C15 C16 120.4(2) . . ? C11 C16 C15 120.6(2) . . ? C18 C17 C4 113.15(13) . . ? C19 C18 C23 117.84(15) . . ? C19 C18 C17 122.05(14) . . ? C23 C18 C17 120.04(14) . . ? C18 C19 C20 121.16(16) . . ? C21 C20 C19 120.19(16) . . ? C20 C21 C22 119.31(16) . . ? C21 C22 C23 120.43(16) . . ? C22 C23 C18 121.06(16) . . ? C2 N1 C8 118.47(14) . . ? C2 N1 C3 125.29(13) . . ? C8 N1 C3 116.23(13) . . ? C7 N2 C3 112.72(12) . . ? C7 N2 C4 112.56(12) . . ? C3 N2 C4 117.22(13) . . ? C5 N3 C9 118.47(13) . . ? C5 N3 C6 123.68(12) . . ? C9 N3 C6 117.81(12) . . ? C6 N4 C7 113.21(12) . . ? C6 N4 C1 116.52(12) . . ? C7 N4 C1 114.50(12) . . ? _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 0.144 _refine_diff_density_min -0.139 _refine_diff_density_rms 0.031 data_nct1006 _database_code_depnum_ccdc_archive 'CCDC 909952' #TrackingRef '13_nct1006.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H28 N4 O2' _chemical_formula_sum 'C23 H28 N4 O2' _chemical_formula_weight 392.49 _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 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 12.9249(4) _cell_length_b 20.3503(5) _cell_length_c 9.3869(4) _cell_angle_alpha 90.00 _cell_angle_beta 124.7300(10) _cell_angle_gamma 90.00 _cell_volume 2029.13(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3416 _cell_measurement_theta_min 3.19 _cell_measurement_theta_max 27.49 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.285 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9834 _exptl_absorpt_correction_T_max 0.9900 _exptl_absorpt_process_details Denzo/Scalepack _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'CCD scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3962 _diffrn_reflns_av_R_equivalents 0.0500 _diffrn_reflns_av_sigmaI/netI 0.0539 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.19 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3962 _reflns_number_gt 3416 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'cOLLECT,Nonius BV, 1997-2001' _computing_cell_refinement DENZO/SCALEPACK _computing_data_reduction DENZO/SCALEPACK _computing_structure_solution SHELXs-97 _computing_structure_refinement SHELXL-97 _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^)+(0.0330P)^2^+2.6661P] 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 0.035(2) _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 1.9(15) _refine_ls_number_reflns 3962 _refine_ls_number_parameters 266 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0644 _refine_ls_R_factor_gt 0.0509 _refine_ls_wR_factor_ref 0.1156 _refine_ls_wR_factor_gt 0.1056 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _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 C1 C 0.1806(2) 0.66052(13) 0.1276(3) 0.0224(5) Uani 1 1 d . . . H1 H 0.2331 0.6425 0.0923 0.027 Uiso 1 1 calc R . . C2 C 0.1345(2) 0.60025(13) 0.1746(3) 0.0231(5) Uani 1 1 d . . . C3 C -0.0251(2) 0.66688(13) 0.1832(3) 0.0239(6) Uani 1 1 d . . . H3A H -0.0876 0.6571 0.2065 0.029 Uiso 1 1 calc R . . H3B H 0.0360 0.6964 0.2735 0.029 Uiso 1 1 calc R . . C4 C 0.0000 0.73895(18) 0.0000 0.0229(8) Uani 1 2 d S . . H4A H 0.0488 0.7672 0.1006 0.027 Uiso 0.50 1 calc PR . . H4B H -0.0488 0.7672 -0.1006 0.027 Uiso 0.50 1 calc PR . . C5 C 0.2726(2) 0.70117(14) 0.2928(3) 0.0255(6) Uani 1 1 d . . . H5A H 0.2251 0.7236 0.3292 0.031 Uiso 1 1 calc R . . H5B H 0.3311 0.6715 0.3852 0.031 Uiso 1 1 calc R . . C6 C 0.3461(2) 0.75128(13) 0.2659(3) 0.0235(6) Uani 1 1 d . . . C7 C 0.3225(3) 0.81807(14) 0.2607(4) 0.0344(7) Uani 1 1 d . . . H7 H 0.2592 0.8321 0.2725 0.041 Uiso 1 1 calc R . . C8 C 0.3908(3) 0.86459(16) 0.2383(4) 0.0397(8) Uani 1 1 d . . . H8 H 0.3731 0.9091 0.2347 0.048 Uiso 1 1 calc R . . C9 C 0.4850(3) 0.84403(16) 0.2215(4) 0.0394(7) Uani 1 1 d . . . H9 H 0.5309 0.8748 0.2058 0.047 Uiso 1 1 calc R . . C10 C 0.5115(3) 0.77791(15) 0.2281(4) 0.0354(7) Uani 1 1 d . . . H10 H 0.5752 0.7642 0.2168 0.043 Uiso 1 1 calc R . . C11 C 0.4430(2) 0.73195(14) 0.2514(4) 0.0294(6) Uani 1 1 d . . . H11 H 0.4621 0.6875 0.2574 0.035 Uiso 1 1 calc R . . C12 C -0.0026(3) 0.54501(15) 0.2352(4) 0.0333(7) Uani 1 1 d . . . H12A H 0.0323 0.5434 0.3569 0.050 Uiso 1 1 calc R . . H12B H 0.0249 0.5073 0.2038 0.050 Uiso 1 1 calc R . . H12C H -0.0928 0.5450 0.1703 0.050 Uiso 1 1 calc R . . C13 C 0.4146(2) 0.40891(12) 0.6154(3) 0.0216(5) Uani 1 1 d . . . H13 H 0.4429 0.3914 0.7295 0.026 Uiso 1 1 calc R . . C14 C 0.3748(2) 0.34851(13) 0.4968(3) 0.0227(6) Uani 1 1 d . . . C15 C 0.3610(2) 0.41472(13) 0.2597(3) 0.0238(5) Uani 1 1 d . . . H15A H 0.3408 0.4041 0.1458 0.029 Uiso 1 1 calc R . . H15B H 0.2966 0.4446 0.2433 0.029 Uiso 1 1 calc R . . C16 C 0.5000 0.48714(17) 0.5000 0.0229(8) Uani 1 2 d S . . H16A H 0.5725 0.5154 0.5427 0.027 Uiso 0.50 1 calc PR . . H16B H 0.4275 0.5154 0.4573 0.027 Uiso 0.50 1 calc PR . . C17 C 0.2964(2) 0.44954(13) 0.5565(3) 0.0232(5) Uani 1 1 d . . . H17A H 0.2647 0.4679 0.4433 0.028 Uiso 1 1 calc R . . H17B H 0.2324 0.4202 0.5433 0.028 Uiso 1 1 calc R . . C18 C 0.3150(2) 0.50508(13) 0.6767(3) 0.0232(6) Uani 1 1 d . . . C19 C 0.3015(2) 0.56934(14) 0.6223(4) 0.0278(6) Uani 1 1 d . . . H19 H 0.2850 0.5781 0.5139 0.033 Uiso 1 1 calc R . . C20 C 0.3120(3) 0.62126(14) 0.7254(4) 0.0312(7) Uani 1 1 d . . . H20 H 0.3025 0.6642 0.6861 0.037 Uiso 1 1 calc R . . C21 C 0.3369(3) 0.60888(16) 0.8876(4) 0.0328(7) Uani 1 1 d . . . H21 H 0.3438 0.6435 0.9573 0.039 Uiso 1 1 calc R . . C22 C 0.3514(2) 0.54456(16) 0.9453(4) 0.0330(7) Uani 1 1 d . . . H22 H 0.3689 0.5358 1.0542 0.040 Uiso 1 1 calc R . . C23 C 0.3396(2) 0.49319(14) 0.8392(4) 0.0276(6) Uani 1 1 d . . . H23 H 0.3483 0.4501 0.8776 0.033 Uiso 1 1 calc R . . C24 C 0.3151(3) 0.29432(13) 0.2304(4) 0.0289(6) Uani 1 1 d . . . H24A H 0.2265 0.2961 0.1413 0.043 Uiso 1 1 calc R . . H24B H 0.3334 0.2562 0.3013 0.043 Uiso 1 1 calc R . . H24C H 0.3608 0.2919 0.1781 0.043 Uiso 1 1 calc R . . N1 N 0.08696(19) 0.70115(10) -0.0191(3) 0.0210(5) Uani 1 1 d . . . N2 N 0.03991(19) 0.60506(11) 0.1967(3) 0.0242(5) Uani 1 1 d . . . N3 N 0.3531(2) 0.35375(10) 0.3381(3) 0.0220(5) Uani 1 1 d . . . N4 N 0.48013(18) 0.44912(11) 0.3546(3) 0.0216(5) Uani 1 1 d . . . O1 O 0.18856(17) 0.54712(9) 0.1943(2) 0.0302(5) Uani 1 1 d . . . O2 O 0.36038(17) 0.29617(9) 0.5502(2) 0.0284(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 0.0232(12) 0.0230(13) 0.0230(13) 0.0014(10) 0.0144(11) 0.0018(10) C2 0.0233(12) 0.0217(13) 0.0226(13) -0.0002(11) 0.0121(11) 0.0017(10) C3 0.0257(12) 0.0259(14) 0.0232(14) 0.0024(11) 0.0158(11) 0.0043(11) C4 0.0242(17) 0.0194(19) 0.026(2) 0.000 0.0154(16) 0.000 C5 0.0231(12) 0.0291(15) 0.0254(14) -0.0007(12) 0.0145(11) -0.0011(11) C6 0.0224(12) 0.0248(14) 0.0188(13) -0.0053(11) 0.0091(11) -0.0032(10) C7 0.0318(15) 0.0304(16) 0.0441(18) -0.0076(14) 0.0235(14) -0.0037(12) C8 0.0385(17) 0.0270(16) 0.054(2) -0.0049(14) 0.0262(16) -0.0034(12) C9 0.0352(16) 0.0352(18) 0.048(2) -0.0006(15) 0.0237(15) -0.0094(13) C10 0.0242(14) 0.0392(18) 0.0435(18) -0.0010(14) 0.0196(14) -0.0003(12) C11 0.0268(14) 0.0282(15) 0.0320(15) 0.0016(12) 0.0160(12) -0.0004(11) C12 0.0317(14) 0.0290(16) 0.0417(17) 0.0087(13) 0.0224(13) -0.0011(12) C13 0.0236(12) 0.0204(13) 0.0226(13) 0.0003(10) 0.0143(11) 0.0004(10) C14 0.0238(12) 0.0211(14) 0.0261(14) 0.0005(11) 0.0159(11) 0.0014(10) C15 0.0247(12) 0.0222(13) 0.0249(13) 0.0007(11) 0.0145(11) -0.0020(11) C16 0.0287(18) 0.0164(18) 0.026(2) 0.000 0.0172(17) 0.000 C17 0.0227(12) 0.0231(13) 0.0263(13) 0.0000(11) 0.0155(11) 0.0018(10) C18 0.0209(12) 0.0244(14) 0.0265(14) -0.0011(11) 0.0147(11) -0.0011(10) C19 0.0322(14) 0.0273(15) 0.0295(15) 0.0019(12) 0.0208(13) 0.0025(11) C20 0.0346(15) 0.0230(15) 0.0412(18) -0.0022(12) 0.0247(14) -0.0009(11) C21 0.0330(14) 0.0356(17) 0.0393(17) -0.0154(14) 0.0263(14) -0.0048(13) C22 0.0291(13) 0.0478(19) 0.0289(15) -0.0026(14) 0.0205(13) 0.0002(13) C23 0.0296(14) 0.0283(15) 0.0311(15) 0.0017(12) 0.0209(13) 0.0010(11) C24 0.0350(15) 0.0225(14) 0.0345(16) -0.0077(12) 0.0229(14) -0.0058(12) N1 0.0241(10) 0.0173(11) 0.0225(11) -0.0019(9) 0.0139(9) -0.0007(8) N2 0.0236(10) 0.0208(11) 0.0296(12) 0.0048(9) 0.0159(10) 0.0009(9) N3 0.0249(11) 0.0181(11) 0.0262(12) -0.0021(9) 0.0165(10) -0.0034(9) N4 0.0200(10) 0.0211(11) 0.0241(11) -0.0004(9) 0.0129(9) -0.0002(8) O1 0.0335(10) 0.0243(10) 0.0326(11) 0.0050(9) 0.0188(9) 0.0079(8) O2 0.0345(11) 0.0205(10) 0.0346(11) 0.0030(8) 0.0222(9) -0.0002(8) _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 N1 1.465(3) . ? C1 C2 1.534(4) . ? C1 C5 1.550(4) . ? C1 H1 0.9800 . ? C2 O1 1.242(3) . ? C2 N2 1.356(3) . ? C3 N1 1.448(3) 2 ? C3 N2 1.478(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 N1 1.455(3) 2 ? C4 N1 1.455(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.509(4) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.388(4) . ? C6 C11 1.392(4) . ? C7 C8 1.390(4) . ? C7 H7 0.9300 . ? C8 C9 1.379(5) . ? C8 H8 0.9300 . ? C9 C10 1.381(4) . ? C9 H9 0.9300 . ? C10 C11 1.389(4) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 N2 1.467(3) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 N4 1.471(3) 2_656 ? C13 C17 1.536(3) . ? C13 C14 1.537(4) . ? C13 H13 0.9800 . ? C14 O2 1.236(3) . ? C14 N3 1.353(3) . ? C15 N4 1.447(3) . ? C15 N3 1.475(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 N4 1.458(3) 2_656 ? C16 N4 1.458(3) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.516(4) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.378(4) . ? C18 C23 1.391(4) . ? C19 C20 1.386(4) . ? C19 H19 0.9300 . ? C20 C21 1.388(4) . ? C20 H20 0.9300 . ? C21 C22 1.388(5) . ? C21 H21 0.9300 . ? C22 C23 1.391(4) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? C24 N3 1.470(3) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? N1 C3 1.448(3) 2 ? N4 C13 1.471(3) 2_656 ? 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 N1 C1 C2 118.2(2) . . ? N1 C1 C5 113.0(2) . . ? C2 C1 C5 110.0(2) . . ? N1 C1 H1 104.7 . . ? C2 C1 H1 104.7 . . ? C5 C1 H1 104.7 . . ? O1 C2 N2 121.3(2) . . ? O1 C2 C1 117.5(2) . . ? N2 C2 C1 121.2(2) . . ? N1 C3 N2 116.3(2) 2 . ? N1 C3 H3A 108.2 2 . ? N2 C3 H3A 108.2 . . ? N1 C3 H3B 108.2 2 . ? N2 C3 H3B 108.2 . . ? H3A C3 H3B 107.4 . . ? N1 C4 N1 116.2(3) 2 . ? N1 C4 H4A 108.2 2 . ? N1 C4 H4A 108.2 . . ? N1 C4 H4B 108.2 2 . ? N1 C4 H4B 108.2 . . ? H4A C4 H4B 107.4 . . ? C6 C5 C1 113.0(2) . . ? C6 C5 H5A 109.0 . . ? C1 C5 H5A 109.0 . . ? C6 C5 H5B 109.0 . . ? C1 C5 H5B 109.0 . . ? H5A C5 H5B 107.8 . . ? C7 C6 C11 117.7(3) . . ? C7 C6 C5 121.4(2) . . ? C11 C6 C5 120.8(2) . . ? C6 C7 C8 121.8(3) . . ? C6 C7 H7 119.1 . . ? C8 C7 H7 119.1 . . ? C9 C8 C7 119.3(3) . . ? C9 C8 H8 120.4 . . ? C7 C8 H8 120.4 . . ? C8 C9 C10 120.2(3) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C9 C10 C11 119.9(3) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C10 C11 C6 121.0(3) . . ? C10 C11 H11 119.5 . . ? C6 C11 H11 119.5 . . ? N2 C12 H12A 109.5 . . ? N2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N4 C13 C17 113.0(2) 2_656 . ? N4 C13 C14 118.3(2) 2_656 . ? C17 C13 C14 108.4(2) . . ? N4 C13 H13 105.3 2_656 . ? C17 C13 H13 105.3 . . ? C14 C13 H13 105.3 . . ? O2 C14 N3 122.0(2) . . ? O2 C14 C13 117.4(2) . . ? N3 C14 C13 120.6(2) . . ? N4 C15 N3 116.9(2) . . ? N4 C15 H15A 108.1 . . ? N3 C15 H15A 108.1 . . ? N4 C15 H15B 108.1 . . ? N3 C15 H15B 108.1 . . ? H15A C15 H15B 107.3 . . ? N4 C16 N4 115.9(3) 2_656 . ? N4 C16 H16A 108.3 2_656 . ? N4 C16 H16A 108.3 . . ? N4 C16 H16B 108.3 2_656 . ? N4 C16 H16B 108.3 . . ? H16A C16 H16B 107.4 . . ? C18 C17 C13 115.5(2) . . ? C18 C17 H17A 108.4 . . ? C13 C17 H17A 108.4 . . ? C18 C17 H17B 108.4 . . ? C13 C17 H17B 108.4 . . ? H17A C17 H17B 107.5 . . ? C19 C18 C23 118.2(2) . . ? C19 C18 C17 119.9(2) . . ? C23 C18 C17 121.8(2) . . ? C18 C19 C20 121.6(3) . . ? C18 C19 H19 119.2 . . ? C20 C19 H19 119.2 . . ? C19 C20 C21 119.8(3) . . ? C19 C20 H20 120.1 . . ? C21 C20 H20 120.1 . . ? C22 C21 C20 119.6(3) . . ? C22 C21 H21 120.2 . . ? C20 C21 H21 120.2 . . ? C21 C22 C23 119.6(3) . . ? C21 C22 H22 120.2 . . ? C23 C22 H22 120.2 . . ? C18 C23 C22 121.2(3) . . ? C18 C23 H23 119.4 . . ? C22 C23 H23 119.4 . . ? N3 C24 H24A 109.5 . . ? N3 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? N3 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C3 N1 C4 112.87(18) 2 . ? C3 N1 C1 112.8(2) 2 . ? C4 N1 C1 117.76(19) . . ? C2 N2 C12 118.4(2) . . ? C2 N2 C3 124.5(2) . . ? C12 N2 C3 117.1(2) . . ? C14 N3 C24 118.1(2) . . ? C14 N3 C15 125.8(2) . . ? C24 N3 C15 116.1(2) . . ? C15 N4 C16 113.02(17) . . ? C15 N4 C13 113.1(2) . 2_656 ? C16 N4 C13 117.75(18) . 2_656 ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.262 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.049 data_nct0910 _database_code_depnum_ccdc_archive 'CCDC 909953' #TrackingRef '15_nct0910.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H20 N4 O2' _chemical_formula_sum 'C11 H20 N4 O2' _chemical_formula_weight 240.31 _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 Tetragonal _symmetry_space_group_name_H-M P43212 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z+1/4' '-x, -y, z+1/2' '-x+1/2, y+1/2, -z+3/4' 'y, x, -z' 'y+1/2, -x+1/2, z+1/4' '-y+1/2, x+1/2, z+3/4' '-y, -x, -z+1/2' _cell_length_a 7.9849(3) _cell_length_b 7.9849(3) _cell_length_c 19.6071(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1250.12(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1261 _cell_measurement_theta_min 3.76 _cell_measurement_theta_max 27.55 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.277 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9648 _exptl_absorpt_correction_T_max 0.9955 _exptl_absorpt_process_details Denzo/scalepack _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'CCD scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2349 _diffrn_reflns_av_R_equivalents 0.0256 _diffrn_reflns_av_sigmaI/netI 0.0433 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.76 _diffrn_reflns_theta_max 27.55 _reflns_number_total 1446 _reflns_number_gt 1261 _reflns_threshold_expression >2\s(I) _computing_data_collection 'cOLLECT,Nonius BV, 1997-2001' _computing_cell_refinement DENZO/SCALEPACK _computing_data_reduction DENZO/SCALEPACK _computing_structure_solution SHELXs-97 _computing_structure_refinement SHELXL-97 _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^ > 2\s(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^)+(0.0627P)^2^+0.1489P] 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 0.112(13) _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(2) _refine_ls_number_reflns 1446 _refine_ls_number_parameters 85 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0507 _refine_ls_R_factor_gt 0.0414 _refine_ls_wR_factor_ref 0.1118 _refine_ls_wR_factor_gt 0.1043 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _refine_ls_shift/su_max 0.016 _refine_ls_shift/su_mean 0.003 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group H3 H 0.7101(19) 0.6056(19) 0.0279(8) 0.019(4) Uiso 1 1 d . . . C1 C 0.41588(19) 0.3017(2) 0.07628(8) 0.0269(4) Uani 1 1 d . . . C2 C 0.63805(19) 0.30683(19) -0.01292(8) 0.0269(4) Uani 1 1 d . . . H2A H 0.7285 0.3225 0.0210 0.032 Uiso 1 1 calc R . . H2B H 0.6793 0.2258 -0.0473 0.032 Uiso 1 1 calc R . . C3 C 0.60550(19) 0.60550(19) 0.0000 0.0270(5) Uani 1 2 d S . . C4 C 0.4696(2) 0.47906(19) 0.09921(7) 0.0269(4) Uani 1 1 d . . . H4 H 0.5887 0.4701 0.1146 0.032 Uiso 1 1 calc R . . C5 C 0.3682(3) 0.5318(2) 0.16122(9) 0.0416(5) Uani 1 1 d . . . H5A H 0.3993 0.6460 0.1744 0.062 Uiso 1 1 calc R . . H5B H 0.3914 0.4552 0.1991 0.062 Uiso 1 1 calc R . . H5C H 0.2486 0.5281 0.1501 0.062 Uiso 1 1 calc R . . C6 C 0.4383(2) 0.0644(2) 0.00140(10) 0.0381(5) Uani 1 1 d . . . H6A H 0.4703 -0.0174 0.0363 0.057 Uiso 1 1 calc R . . H6B H 0.4910 0.0347 -0.0421 0.057 Uiso 1 1 calc R . . H6C H 0.3162 0.0642 -0.0040 0.057 Uiso 1 1 calc R . . N1 N 0.49370(15) 0.23087(15) 0.02215(6) 0.0265(4) Uani 1 1 d . . . N2 N 0.46494(15) 0.61070(15) 0.04679(7) 0.0248(3) Uani 1 1 d . . . O1 O 0.30428(16) 0.22696(16) 0.10702(6) 0.0401(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 0.0280(8) 0.0264(8) 0.0265(8) 0.0058(6) -0.0016(6) -0.0012(6) C2 0.0249(7) 0.0279(8) 0.0279(8) -0.0016(6) 0.0008(6) 0.0037(6) C3 0.0250(7) 0.0250(7) 0.0310(12) -0.0003(7) 0.0003(7) -0.0038(9) C4 0.0276(8) 0.0289(8) 0.0244(8) -0.0009(6) -0.0028(6) -0.0001(7) C5 0.0528(11) 0.0454(11) 0.0265(8) -0.0031(8) 0.0021(8) 0.0046(9) C6 0.0476(10) 0.0217(8) 0.0449(10) -0.0024(8) -0.0074(9) -0.0041(7) N1 0.0306(7) 0.0204(7) 0.0286(7) 0.0004(5) -0.0015(6) -0.0017(5) N2 0.0241(7) 0.0219(6) 0.0284(7) -0.0015(5) -0.0022(5) -0.0001(5) O1 0.0410(7) 0.0400(8) 0.0393(7) 0.0090(6) 0.0068(6) -0.0104(6) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O1 1.2304(18) . ? C1 N1 1.354(2) . ? C1 C4 1.546(2) . ? C2 N2 1.4430(19) 5 ? C2 N1 1.4728(19) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 N2 1.4501(17) . ? C3 N2 1.4501(17) 5 ? C3 H3 0.999(16) . ? C4 N2 1.4707(19) . ? C4 C5 1.520(2) . ? C4 H4 1.0000 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 N1 1.4586(19) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? N2 C2 1.4430(19) 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 O1 C1 N1 120.92(15) . . ? O1 C1 C4 120.17(14) . . ? N1 C1 C4 118.91(13) . . ? N2 C2 N1 117.17(13) 5 . ? N2 C2 H2A 108.0 5 . ? N1 C2 H2A 108.0 . . ? N2 C2 H2B 108.0 5 . ? N1 C2 H2B 108.0 . . ? H2A C2 H2B 107.2 . . ? N2 C3 N2 116.39(17) . 5 ? N2 C3 H3 107.5(9) . . ? N2 C3 H3 108.9(9) 5 . ? N2 C4 C5 110.35(13) . . ? N2 C4 C1 116.38(12) . . ? C5 C4 C1 109.80(13) . . ? N2 C4 H4 106.6 . . ? C5 C4 H4 106.6 . . ? C1 C4 H4 106.6 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N1 C6 H6A 109.5 . . ? N1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C1 N1 C6 117.40(13) . . ? C1 N1 C2 123.58(12) . . ? C6 N1 C2 118.85(13) . . ? C2 N2 C3 112.98(11) 5 . ? C2 N2 C4 116.85(12) 5 . ? C3 N2 C4 113.72(10) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.55 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.184 _refine_diff_density_min -0.170 _refine_diff_density_rms 0.036 data_nct0908 _database_code_depnum_ccdc_archive 'CCDC 909954' #TrackingRef '17_nct0908.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H28 N4 O2' _chemical_formula_sum 'C15 H28 N4 O2' _chemical_formula_weight 296.41 _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 Orthorhombic _symmetry_space_group_name_H-M C2221 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x, -y, -z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x+1/2, y+1/2, -z+1/2' _cell_length_a 8.1565(8) _cell_length_b 12.7760(15) _cell_length_c 15.5401(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1619.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 971 _cell_measurement_theta_min 3.96 _cell_measurement_theta_max 24.75 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.216 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9757 _exptl_absorpt_correction_T_max 0.9959 _exptl_absorpt_process_details Denzo/Scalepack _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'CCD scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1325 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0942 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.96 _diffrn_reflns_theta_max 24.75 _reflns_number_total 1325 _reflns_number_gt 971 _reflns_threshold_expression >2\s(I) _computing_data_collection 'cOLLECT,Nonius BV, 1997-2001' _computing_cell_refinement DENZO/SCALEPACK _computing_data_reduction DENZO/SCALEPACK _computing_structure_solution SHELXs-97 _computing_structure_refinement SHELXL-97 _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^ > 2\s(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^)+(0.0544P)^2^+2.8109P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 5(4) _refine_ls_number_reflns 1325 _refine_ls_number_parameters 102 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1156 _refine_ls_R_factor_gt 0.0775 _refine_ls_wR_factor_ref 0.1639 _refine_ls_wR_factor_gt 0.1471 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.067 _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 C1 C 0.6880(5) 0.0246(4) 0.7660(3) 0.0341(10) Uani 1 1 d . . . C2 C 0.5959(6) 0.1292(4) 0.6378(3) 0.0354(11) Uani 1 1 d . . . H2A H 0.6910 0.1773 0.6374 0.043 Uiso 1 1 calc R . . H2B H 0.5700 0.1122 0.5772 0.043 Uiso 1 1 calc R . . C3 C 0.5000 0.2459(5) 0.7500 0.0335(15) Uani 1 2 d SD . . C4 C 0.6972(5) 0.1266(3) 0.8197(3) 0.0345(11) Uani 1 1 d . . . H4 H 0.7755 0.1736 0.7888 0.041 Uiso 1 1 calc R . . C5 C 0.7759(6) 0.1029(4) 0.9079(3) 0.0398(12) Uani 1 1 d . . . H5 H 0.7253 0.0376 0.9313 0.048 Uiso 1 1 calc R . . C6 C 0.9587(6) 0.0828(5) 0.8941(3) 0.0556(15) Uani 1 1 d . . . H6A H 1.0107 0.1463 0.8715 0.083 Uiso 1 1 calc R . . H6B H 0.9730 0.0254 0.8530 0.083 Uiso 1 1 calc R . . H6C H 1.0097 0.0640 0.9491 0.083 Uiso 1 1 calc R . . C7 C 0.7532(7) 0.1898(4) 0.9738(3) 0.0477(13) Uani 1 1 d . . . H7A H 0.7939 0.1662 1.0299 0.072 Uiso 1 1 calc R . . H7B H 0.6365 0.2071 0.9785 0.072 Uiso 1 1 calc R . . H7C H 0.8145 0.2519 0.9556 0.072 Uiso 1 1 calc R . . C8 C 0.6494(6) -0.0649(4) 0.6307(3) 0.0462(13) Uani 1 1 d . . . H8A H 0.7589 -0.0964 0.6337 0.069 Uiso 1 1 calc R . . H8B H 0.6229 -0.0488 0.5706 0.069 Uiso 1 1 calc R . . H8C H 0.5684 -0.1142 0.6536 0.069 Uiso 1 1 calc R . . N1 N 0.6465(4) 0.0313(3) 0.6813(2) 0.0351(9) Uani 1 1 d . . . N2 N 0.5424(4) 0.1847(3) 0.8262(2) 0.0339(9) Uani 1 1 d . . . O1 O 0.7201(4) -0.0607(2) 0.79889(19) 0.0420(9) Uani 1 1 d . . . H3 H 0.402(3) 0.289(3) 0.764(3) 0.050 Uiso 1 1 d 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 0.026(2) 0.035(2) 0.041(3) 0.003(2) 0.0016(19) 0.004(2) C2 0.035(3) 0.040(2) 0.031(2) 0.002(2) 0.0027(19) 0.004(2) C3 0.032(4) 0.037(4) 0.032(3) 0.000 -0.004(3) 0.000 C4 0.031(2) 0.036(2) 0.036(2) 0.004(2) 0.003(2) -0.0003(19) C5 0.042(3) 0.044(3) 0.033(2) 0.003(2) -0.007(2) -0.003(2) C6 0.041(3) 0.075(3) 0.051(3) -0.002(3) -0.010(3) 0.014(2) C7 0.060(3) 0.047(3) 0.037(3) -0.002(2) -0.006(2) -0.008(3) C8 0.052(3) 0.044(3) 0.043(3) -0.010(2) 0.005(2) 0.006(2) N1 0.042(2) 0.032(2) 0.0308(19) -0.0037(17) 0.0038(18) 0.0060(16) N2 0.035(2) 0.0324(18) 0.0347(19) -0.0003(19) -0.0010(17) -0.0023(17) O1 0.050(2) 0.0332(19) 0.0432(18) -0.0008(14) -0.0041(15) 0.0105(14) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O1 1.232(5) . ? C1 N1 1.362(5) . ? C1 C4 1.549(6) . ? C2 N2 1.445(5) 4_656 ? C2 N1 1.480(6) . ? C3 N2 1.460(5) 4_656 ? C3 N2 1.460(5) . ? C4 N2 1.468(5) . ? C4 C5 1.544(6) . ? C5 C7 1.521(6) . ? C5 C6 1.528(7) . ? C8 N1 1.460(6) . ? N2 C2 1.445(5) 4_656 ? 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 O1 C1 N1 120.6(4) . . ? O1 C1 C4 120.7(4) . . ? N1 C1 C4 118.7(4) . . ? N2 C2 N1 117.1(3) 4_656 . ? N2 C3 N2 115.3(5) 4_656 . ? N2 C4 C5 113.4(3) . . ? N2 C4 C1 114.9(3) . . ? C5 C4 C1 109.5(3) . . ? C7 C5 C6 109.6(4) . . ? C7 C5 C4 113.8(4) . . ? C6 C5 C4 108.3(4) . . ? C1 N1 C8 117.7(4) . . ? C1 N1 C2 124.3(3) . . ? C8 N1 C2 118.0(3) . . ? C2 N2 C3 113.1(3) 4_656 . ? C2 N2 C4 116.7(3) 4_656 . ? C3 N2 C4 114.8(3) . . ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 24.75 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.183 _refine_diff_density_min -0.212 _refine_diff_density_rms 0.048 data_nct0906 _database_code_depnum_ccdc_archive 'CCDC 909955' #TrackingRef '18_nct0906.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H28 N4 O2' _chemical_formula_sum 'C15 H28 N4 O2' _chemical_formula_weight 296.41 _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 Orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 14.0399(3) _cell_length_b 8.1422(2) _cell_length_c 14.4418(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1650.92(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3271 _cell_measurement_theta_min 3.17 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.193 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9723 _exptl_absorpt_correction_T_max 0.9936 _exptl_absorpt_process_details Denzo/Scalepack _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'CCD scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3767 _diffrn_reflns_av_R_equivalents 0.0300 _diffrn_reflns_av_sigmaI/netI 0.0381 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.17 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3767 _reflns_number_gt 3271 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'cOLLECT,Nonius BV, 1997-2001' _computing_cell_refinement DENZO/SCALEPACK _computing_data_reduction DENZO/SCALEPACK _computing_structure_solution SHELXs-97 _computing_structure_refinement SHELXL-97 _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^)+(0.0405P)^2^+0.6402P] 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 0.104(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1.5(14) _refine_ls_number_reflns 3767 _refine_ls_number_parameters 197 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0570 _refine_ls_R_factor_gt 0.0450 _refine_ls_wR_factor_ref 0.1057 _refine_ls_wR_factor_gt 0.0982 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 C1 C 0.25501(13) 0.8944(2) 0.65695(12) 0.0267(4) Uani 1 1 d . . . C2 C 0.20537(14) 0.6166(2) 0.71727(12) 0.0263(4) Uani 1 1 d . . . H2A H 0.1522 0.5409 0.7029 0.032 Uiso 1 1 calc R . . H2B H 0.2654 0.5574 0.7038 0.032 Uiso 1 1 calc R . . C3 C 0.29255(13) 0.7121(2) 0.85176(12) 0.0264(4) Uani 1 1 d . . . H3A H 0.3433 0.6344 0.8331 0.032 Uiso 1 1 calc R . . H3B H 0.2886 0.7094 0.9202 0.032 Uiso 1 1 calc R . . C4 C 0.33948(12) 0.9030(2) 0.72512(12) 0.0238(4) Uani 1 1 d . . . H4 H 0.3622 1.0192 0.7212 0.029 Uiso 1 1 calc R . . C5 C 0.11504(12) 0.7374(2) 0.84358(12) 0.0248(4) Uani 1 1 d . . . H5 H 0.0625 0.6742 0.8133 0.030 Uiso 1 1 calc R . . C6 C 0.10092(12) 0.9158(2) 0.81006(12) 0.0265(4) Uani 1 1 d . . . C7 C 0.26330(12) 1.0020(2) 0.86583(12) 0.0268(4) Uani 1 1 d . . . H7A H 0.2994 1.1064 0.8644 0.032 Uiso 1 1 calc R . . H7B H 0.2536 0.9728 0.9317 0.032 Uiso 1 1 calc R . . C8 C 0.42376(13) 0.7997(2) 0.68864(13) 0.0297(4) Uani 1 1 d . . . H8 H 0.4055 0.6812 0.6920 0.036 Uiso 1 1 calc R . . C9 C 0.51171(14) 0.8252(3) 0.74810(17) 0.0425(5) Uani 1 1 d . . . H9A H 0.5271 0.9425 0.7505 0.064 Uiso 1 1 calc R . . H9B H 0.5654 0.7648 0.7213 0.064 Uiso 1 1 calc R . . H9C H 0.4994 0.7848 0.8109 0.064 Uiso 1 1 calc R . . C10 C 0.44554(18) 0.8414(3) 0.58787(15) 0.0450(6) Uani 1 1 d . . . H10A H 0.5000 0.7761 0.5667 0.067 Uiso 1 1 calc R . . H10B H 0.4608 0.9585 0.5827 0.067 Uiso 1 1 calc R . . H10C H 0.3898 0.8164 0.5495 0.067 Uiso 1 1 calc R . . C11 C 0.12338(15) 0.7527(3) 0.58429(14) 0.0380(5) Uani 1 1 d . . . H11A H 0.1436 0.6827 0.5327 0.057 Uiso 1 1 calc R . . H11B H 0.1104 0.8637 0.5614 0.057 Uiso 1 1 calc R . . H11C H 0.0655 0.7072 0.6122 0.057 Uiso 1 1 calc R . . C12 C 0.09449(13) 0.7229(3) 0.94863(12) 0.0304(4) Uani 1 1 d . . . H12 H 0.1363 0.8015 0.9830 0.037 Uiso 1 1 calc R . . C13 C 0.11307(17) 0.5486(3) 0.98359(15) 0.0414(5) Uani 1 1 d . . . H13A H 0.0756 0.4705 0.9471 0.062 Uiso 1 1 calc R . . H13B H 0.0946 0.5408 1.0489 0.062 Uiso 1 1 calc R . . H13C H 0.1809 0.5229 0.9773 0.062 Uiso 1 1 calc R . . C14 C -0.01028(14) 0.7682(3) 0.96565(14) 0.0387(5) Uani 1 1 d . . . H14A H -0.0242 0.7611 1.0320 0.058 Uiso 1 1 calc R . . H14B H -0.0515 0.6918 0.9318 0.058 Uiso 1 1 calc R . . H14C H -0.0220 0.8804 0.9440 0.058 Uiso 1 1 calc R . . C15 C 0.15044(16) 1.1989(2) 0.78979(15) 0.0376(5) Uani 1 1 d . . . H15A H 0.0816 1.2176 0.7865 0.056 Uiso 1 1 calc R . . H15B H 0.1783 1.2118 0.7280 0.056 Uiso 1 1 calc R . . H15C H 0.1792 1.2788 0.8322 0.056 Uiso 1 1 calc R . . N1 N 0.19892(11) 0.75918(19) 0.65389(10) 0.0272(3) Uani 1 1 d . . . N2 N 0.20283(10) 0.65258(18) 0.81478(10) 0.0242(3) Uani 1 1 d . . . N3 N 0.32150(10) 0.87623(18) 0.82397(10) 0.0242(3) Uani 1 1 d . . . N4 N 0.16886(11) 1.03181(18) 0.82386(10) 0.0269(3) Uani 1 1 d . . . O1 O 0.24334(10) 1.01050(17) 0.60319(9) 0.0351(3) Uani 1 1 d . . . O2 O 0.02465(9) 0.95148(17) 0.77201(10) 0.0365(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 0.0295(9) 0.0283(9) 0.0224(8) -0.0012(7) 0.0030(7) 0.0015(7) C2 0.0285(9) 0.0238(9) 0.0267(9) -0.0002(7) 0.0020(7) -0.0016(7) C3 0.0243(8) 0.0297(9) 0.0250(8) 0.0037(8) -0.0004(7) 0.0006(7) C4 0.0248(8) 0.0242(9) 0.0225(8) -0.0010(7) 0.0018(7) -0.0036(7) C5 0.0226(8) 0.0255(9) 0.0264(8) -0.0011(8) 0.0020(7) -0.0004(7) C6 0.0246(9) 0.0287(9) 0.0263(9) -0.0019(7) 0.0026(7) 0.0018(7) C7 0.0258(9) 0.0305(9) 0.0243(8) -0.0039(7) -0.0016(7) -0.0032(7) C8 0.0304(9) 0.0241(9) 0.0344(10) -0.0008(8) 0.0074(8) -0.0006(7) C9 0.0274(10) 0.0439(12) 0.0563(13) -0.0036(11) 0.0043(9) 0.0021(9) C10 0.0531(13) 0.0449(13) 0.0369(11) -0.0018(10) 0.0204(10) 0.0035(11) C11 0.0396(11) 0.0442(12) 0.0303(9) 0.0013(9) -0.0105(8) -0.0086(10) C12 0.0308(9) 0.0343(10) 0.0262(9) -0.0018(8) 0.0049(7) -0.0037(8) C13 0.0521(13) 0.0390(12) 0.0331(10) 0.0091(9) 0.0121(10) 0.0016(10) C14 0.0353(11) 0.0442(12) 0.0364(10) -0.0035(9) 0.0100(9) -0.0014(10) C15 0.0418(11) 0.0242(10) 0.0468(12) -0.0002(9) 0.0007(9) 0.0041(8) N1 0.0288(8) 0.0290(8) 0.0237(7) 0.0015(6) -0.0039(6) -0.0043(7) N2 0.0239(7) 0.0250(7) 0.0236(7) 0.0007(6) 0.0012(6) 0.0010(6) N3 0.0252(7) 0.0254(8) 0.0219(7) 0.0005(6) 0.0006(6) -0.0008(6) N4 0.0270(7) 0.0231(8) 0.0305(8) -0.0015(6) -0.0005(6) 0.0012(6) O1 0.0449(8) 0.0334(7) 0.0270(6) 0.0077(6) -0.0045(6) -0.0022(6) O2 0.0257(7) 0.0348(8) 0.0489(8) 0.0028(7) -0.0073(6) 0.0027(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.234(2) . ? C1 N1 1.354(2) . ? C1 C4 1.543(2) . ? C2 N2 1.439(2) . ? C2 N1 1.481(2) . ? C3 N2 1.451(2) . ? C3 N3 1.454(2) . ? C4 N3 1.466(2) . ? C4 C8 1.544(2) . ? C5 N2 1.473(2) . ? C5 C6 1.544(3) . ? C5 C12 1.549(2) . ? C6 O2 1.238(2) . ? C6 N4 1.357(2) . ? C7 N3 1.443(2) . ? C7 N4 1.478(2) . ? C8 C9 1.518(3) . ? C8 C10 1.525(3) . ? C11 N1 1.462(2) . ? C12 C13 1.529(3) . ? C12 C14 1.536(3) . ? C15 N4 1.470(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 O1 C1 N1 121.67(17) . . ? O1 C1 C4 117.95(17) . . ? N1 C1 C4 120.31(15) . . ? N2 C2 N1 116.32(15) . . ? N2 C3 N3 116.61(15) . . ? N3 C4 C1 118.83(14) . . ? N3 C4 C8 112.54(14) . . ? C1 C4 C8 110.28(14) . . ? N2 C5 C6 117.39(14) . . ? N2 C5 C12 113.39(14) . . ? C6 C5 C12 110.76(15) . . ? O2 C6 N4 120.65(17) . . ? O2 C6 C5 118.09(16) . . ? N4 C6 C5 121.24(15) . . ? N3 C7 N4 116.92(14) . . ? C9 C8 C10 110.26(18) . . ? C9 C8 C4 110.85(15) . . ? C10 C8 C4 110.98(16) . . ? C13 C12 C14 109.45(17) . . ? C13 C12 C5 111.23(16) . . ? C14 C12 C5 108.48(16) . . ? C1 N1 C11 118.28(16) . . ? C1 N1 C2 125.56(14) . . ? C11 N1 C2 116.14(15) . . ? C2 N2 C3 113.99(14) . . ? C2 N2 C5 113.12(14) . . ? C3 N2 C5 117.78(14) . . ? C7 N3 C3 112.24(14) . . ? C7 N3 C4 113.59(14) . . ? C3 N3 C4 116.99(14) . . ? C6 N4 C15 118.14(15) . . ? C6 N4 C7 125.20(15) . . ? C15 N4 C7 116.56(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 0.166 _refine_diff_density_min -0.153 _refine_diff_density_rms 0.039 data_nct0907 _database_code_depnum_ccdc_archive 'CCDC 909956' #TrackingRef '6_nct0907.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H16 N4 O2, H2 O' _chemical_formula_sum 'C9 H18 N4 O3' _chemical_formula_weight 230.27 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/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.6979(2) _cell_length_b 12.3452(5) _cell_length_c 13.8609(4) _cell_angle_alpha 90.00 _cell_angle_beta 103.061(2) _cell_angle_gamma 90.00 _cell_volume 1116.46(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1754 _cell_measurement_theta_min 3.53 _cell_measurement_theta_max 27.52 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.370 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9694 _exptl_absorpt_correction_T_max 0.9958 _exptl_absorpt_process_details Denzo/Scalepack _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'CCD scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4759 _diffrn_reflns_av_R_equivalents 0.0532 _diffrn_reflns_av_sigmaI/netI 0.0652 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.53 _diffrn_reflns_theta_max 27.52 _reflns_number_total 2553 _reflns_number_gt 1754 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'cOLLECT,Nonius BV, 1997-2001' _computing_cell_refinement DENZO/SCALEPACK _computing_data_reduction DENZO/SCALEPACK _computing_structure_solution SHELXs-97 _computing_structure_refinement SHELXL-97 _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^)+(0.0505P)^2^+0.3707P] 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 0.064(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2553 _refine_ls_number_parameters 156 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0896 _refine_ls_R_factor_gt 0.0540 _refine_ls_wR_factor_ref 0.1291 _refine_ls_wR_factor_gt 0.1145 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 C1 C 0.0801(3) 0.22216(15) 0.76255(13) 0.0253(4) Uani 1 1 d . . . C2 C 0.3327(3) 0.07095(15) 0.80717(14) 0.0282(5) Uani 1 1 d . . . H2A H 0.2320 0.0126 0.7836 0.034 Uiso 1 1 calc R . . H2B H 0.4616 0.0506 0.7882 0.034 Uiso 1 1 calc R . . C3 C 0.1902(3) 0.06493(15) 0.95326(15) 0.0281(5) Uani 1 1 d . . . H3A H 0.2342 0.0521 1.0255 0.034 Uiso 1 1 calc R . . H3B H 0.1124 0.0003 0.9236 0.034 Uiso 1 1 calc R . . C4 C -0.0447(3) 0.17719(15) 0.83294(14) 0.0247(4) Uani 1 1 d . . . H4A H -0.1604 0.2276 0.8314 0.030 Uiso 1 1 calc R . . H4B H -0.1048 0.1076 0.8049 0.030 Uiso 1 1 calc R . . C5 C 0.5148(3) 0.15712(15) 0.96131(14) 0.0250(4) Uani 1 1 d . . . H5A H 0.6479 0.1425 0.9440 0.030 Uiso 1 1 calc R . . H5B H 0.5359 0.1465 1.0337 0.030 Uiso 1 1 calc R . . C6 C 0.4651(3) 0.27687(16) 0.94000(13) 0.0242(4) Uani 1 1 d . . . C7 C 0.1334(3) 0.25279(15) 0.99184(14) 0.0271(5) Uani 1 1 d . . . H7A H 0.1982 0.2304 1.0604 0.032 Uiso 1 1 calc R . . H7B H 0.0170 0.3008 0.9955 0.032 Uiso 1 1 calc R . . C8 C 0.3646(3) 0.21513(18) 0.68230(15) 0.0334(5) Uani 1 1 d . . . H8A H 0.2946 0.1924 0.6155 0.050 Uiso 1 1 calc R . . H8B H 0.5052 0.1872 0.6975 0.050 Uiso 1 1 calc R . . H8C H 0.3676 0.2944 0.6859 0.050 Uiso 1 1 calc R . . C9 C 0.2424(3) 0.43339(15) 0.93792(16) 0.0340(5) Uani 1 1 d . . . H9A H 0.2502 0.4683 1.0022 0.051 Uiso 1 1 calc R . . H9B H 0.1048 0.4433 0.8960 0.051 Uiso 1 1 calc R . . H9C H 0.3437 0.4661 0.9056 0.051 Uiso 1 1 calc R . . N1 N 0.2548(2) 0.17237(12) 0.75415(11) 0.0252(4) Uani 1 1 d . . . N2 N 0.3715(2) 0.07453(12) 0.91335(11) 0.0243(4) Uani 1 1 d . . . N3 N 0.0529(2) 0.15779(13) 0.93701(11) 0.0251(4) Uani 1 1 d . . . N4 N 0.2852(2) 0.31712(12) 0.95285(11) 0.0248(4) Uani 1 1 d . . . O1 O 0.0143(2) 0.30230(11) 0.71041(10) 0.0336(4) Uani 1 1 d . . . O2 O 0.5944(2) 0.33536(11) 0.91445(11) 0.0328(4) Uani 1 1 d . . . O3 O -0.2272(3) -0.05436(14) 0.74002(16) 0.0542(5) Uani 1 1 d . . . H2O H -0.176(5) -0.081(3) 0.692(2) 0.078(10) Uiso 1 1 d . . . H1O H -0.319(5) -0.104(3) 0.756(2) 0.094(11) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0257(9) 0.0271(10) 0.0216(9) -0.0009(8) 0.0021(7) -0.0019(8) C2 0.0321(10) 0.0240(10) 0.0291(10) -0.0017(8) 0.0084(8) 0.0028(8) C3 0.0282(10) 0.0247(10) 0.0329(11) 0.0065(8) 0.0097(8) 0.0007(8) C4 0.0188(8) 0.0254(10) 0.0295(10) 0.0017(8) 0.0046(7) -0.0006(7) C5 0.0204(8) 0.0282(10) 0.0266(10) 0.0028(8) 0.0058(7) 0.0028(8) C6 0.0235(9) 0.0278(10) 0.0210(9) -0.0020(8) 0.0046(7) -0.0013(8) C7 0.0254(9) 0.0304(11) 0.0272(10) 0.0003(9) 0.0097(8) 0.0042(8) C8 0.0312(10) 0.0420(12) 0.0292(11) 0.0055(9) 0.0113(8) 0.0028(9) C9 0.0340(11) 0.0244(11) 0.0428(12) -0.0029(9) 0.0070(9) 0.0033(9) N1 0.0268(8) 0.0278(9) 0.0213(8) 0.0019(7) 0.0063(6) 0.0012(7) N2 0.0243(8) 0.0233(8) 0.0264(8) 0.0020(7) 0.0077(6) 0.0013(7) N3 0.0236(8) 0.0260(8) 0.0269(9) 0.0044(7) 0.0080(6) 0.0024(7) N4 0.0245(8) 0.0222(8) 0.0279(9) -0.0015(7) 0.0061(6) 0.0011(6) O1 0.0359(8) 0.0336(8) 0.0307(8) 0.0086(6) 0.0059(6) 0.0067(6) O2 0.0269(7) 0.0294(8) 0.0436(9) 0.0012(6) 0.0111(6) -0.0038(6) O3 0.0534(11) 0.0403(10) 0.0774(14) -0.0253(9) 0.0325(10) -0.0155(8) _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 O1 1.245(2) . ? C1 N1 1.350(2) . ? C1 C4 1.526(3) . ? C2 N2 1.436(2) . ? C2 N1 1.486(2) . ? C3 N2 1.449(2) . ? C3 N3 1.455(2) . ? C4 N3 1.463(2) . ? C5 N2 1.454(2) . ? C5 C6 1.529(3) . ? C6 O2 1.239(2) . ? C6 N4 1.352(2) . ? C7 N3 1.435(2) . ? C7 N4 1.485(2) . ? C8 N1 1.464(3) . ? C9 N4 1.469(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 O1 C1 N1 120.76(18) . . ? O1 C1 C4 119.16(17) . . ? N1 C1 C4 120.02(16) . . ? N2 C2 N1 116.29(15) . . ? N2 C3 N3 115.56(15) . . ? N3 C4 C1 120.18(14) . . ? N2 C5 C6 119.80(14) . . ? O2 C6 N4 121.66(17) . . ? O2 C6 C5 118.85(16) . . ? N4 C6 C5 119.44(16) . . ? N3 C7 N4 116.78(15) . . ? C1 N1 C8 118.24(16) . . ? C1 N1 C2 123.76(16) . . ? C8 N1 C2 117.77(16) . . ? C2 N2 C3 114.55(15) . . ? C2 N2 C5 115.98(15) . . ? C3 N2 C5 113.99(15) . . ? C7 N3 C3 114.42(14) . . ? C7 N3 C4 114.79(14) . . ? C3 N3 C4 114.07(15) . . ? C6 N4 C9 119.47(16) . . ? C6 N4 C7 123.74(15) . . ? C9 N4 C7 116.48(15) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.206 _refine_diff_density_min -0.208 _refine_diff_density_rms 0.051