# Electronic Supplementary Material (ESI) for RSC Advances # 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_mo_20110604c_0m #TrackingRef '3aa.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H13 N3 O' _chemical_formula_sum 'C16 H13 N3 O' _chemical_formula_weight 263.29 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 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' 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' '-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 8.5996(13) _cell_length_b 14.555(2) _cell_length_c 20.633(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2582.6(6) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3526 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 27.32 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.354 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9844 _exptl_absorpt_correction_T_max 0.9904 _exptl_absorpt_process_details 'SADABS (Bruker, 2002)' _diffrn_ambient_temperature 298(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 'Bruker APEX II area-detector diffractometer' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10484 _diffrn_reflns_av_R_equivalents 0.0825 _diffrn_reflns_av_sigmaI/netI 0.0583 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 25.10 _reflns_number_total 2292 _reflns_number_gt 1326 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (Bruker, 2002)' _computing_publication_material 'SHELXL-97 (Bruker, 2002)' _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^)+(0.0937P)^2^] 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 0.0045(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2292 _refine_ls_number_parameters 183 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1025 _refine_ls_R_factor_gt 0.0511 _refine_ls_wR_factor_ref 0.1744 _refine_ls_wR_factor_gt 0.1391 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.4064(3) 0.23448(15) 0.18650(10) 0.0583(7) Uani 1 1 d . . . N1 N 0.3978(3) 0.30096(17) 0.08740(11) 0.0430(6) Uani 1 1 d . . . H1 H 0.4402 0.2543 0.0689 0.052 Uiso 1 1 calc R . . N2 N 0.2057(3) 0.41325(16) 0.06418(11) 0.0375(6) Uani 1 1 d . . . N3 N 0.1004(3) 0.34908(17) -0.03121(11) 0.0404(6) Uani 1 1 d . . . C1 C 0.2679(4) 0.3270(2) -0.12373(14) 0.0471(8) Uani 1 1 d . . . H1A H 0.1804 0.3136 -0.1484 0.056 Uiso 1 1 calc R . . C2 C 0.4117(4) 0.3258(2) -0.15193(15) 0.0523(9) Uani 1 1 d . . . H2 H 0.4215 0.3106 -0.1955 0.063 Uiso 1 1 calc R . . C3 C 0.5430(4) 0.3469(2) -0.11604(16) 0.0535(9) Uani 1 1 d . . . H3 H 0.6405 0.3471 -0.1355 0.064 Uiso 1 1 calc R . . C4 C 0.5279(4) 0.3678(2) -0.05071(15) 0.0482(8) Uani 1 1 d . . . H4 H 0.6156 0.3823 -0.0264 0.058 Uiso 1 1 calc R . . C5 C 0.3826(3) 0.36711(19) -0.02163(14) 0.0384(7) Uani 1 1 d . . . C6 C 0.2515(4) 0.34832(19) -0.05812(13) 0.0392(7) Uani 1 1 d . . . C7 C 0.0836(3) 0.38145(19) 0.02689(14) 0.0379(7) Uani 1 1 d . . . C8 C 0.3633(3) 0.38346(19) 0.04944(13) 0.0372(7) Uani 1 1 d . . . H8 H 0.4354 0.4321 0.0626 0.045 Uiso 1 1 calc R . . C9 C -0.0777(3) 0.3861(2) 0.05369(15) 0.0465(8) Uani 1 1 d . . . H9A H -0.1118 0.4488 0.0546 0.070 Uiso 1 1 calc R . . H9B H -0.0784 0.3616 0.0969 0.070 Uiso 1 1 calc R . . H9C H -0.1464 0.3507 0.0268 0.070 Uiso 1 1 calc R . . C10 C 0.3638(3) 0.2975(2) 0.15128(14) 0.0431(8) Uani 1 1 d . . . C11 C 0.2657(3) 0.3749(2) 0.17531(14) 0.0401(7) Uani 1 1 d . . . C12 C 0.1871(3) 0.43173(19) 0.13233(14) 0.0387(7) Uani 1 1 d . . . C13 C 0.0971(4) 0.5041(2) 0.15459(16) 0.0503(9) Uani 1 1 d . . . H13 H 0.0478 0.5434 0.1256 0.060 Uiso 1 1 calc R . . C14 C 0.0818(4) 0.5169(2) 0.22037(17) 0.0585(9) Uani 1 1 d . . . H14 H 0.0206 0.5648 0.2359 0.070 Uiso 1 1 calc R . . C15 C 0.1561(4) 0.4595(3) 0.26357(16) 0.0582(10) Uani 1 1 d . . . H15 H 0.1436 0.4685 0.3079 0.070 Uiso 1 1 calc R . . C16 C 0.2482(4) 0.3895(2) 0.24169(15) 0.0525(9) Uani 1 1 d . . . H16 H 0.2991 0.3516 0.2711 0.063 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 0.0806(17) 0.0513(14) 0.0430(13) 0.0094(11) -0.0012(11) 0.0209(12) N1 0.0551(16) 0.0388(14) 0.0351(14) 0.0002(11) -0.0019(11) 0.0118(12) N2 0.0378(14) 0.0389(14) 0.0359(13) -0.0025(11) -0.0049(10) 0.0041(10) N3 0.0446(14) 0.0399(14) 0.0369(14) 0.0015(11) -0.0055(11) -0.0028(11) C1 0.061(2) 0.0435(19) 0.0369(17) 0.0038(14) -0.0065(15) -0.0035(15) C2 0.073(2) 0.048(2) 0.0360(18) 0.0047(14) 0.0075(16) -0.0002(17) C3 0.062(2) 0.050(2) 0.048(2) 0.0098(16) 0.0150(16) 0.0025(16) C4 0.0488(19) 0.048(2) 0.0476(19) 0.0069(15) 0.0011(15) -0.0002(15) C5 0.0422(17) 0.0356(16) 0.0373(16) 0.0033(12) -0.0022(13) 0.0004(13) C6 0.0518(18) 0.0323(16) 0.0335(16) 0.0053(12) -0.0034(13) -0.0008(13) C7 0.0423(17) 0.0305(16) 0.0410(17) 0.0052(12) -0.0050(13) 0.0013(12) C8 0.0364(16) 0.0360(16) 0.0393(16) 0.0009(13) -0.0059(12) -0.0005(12) C9 0.0381(17) 0.0469(19) 0.0547(19) -0.0019(15) -0.0029(13) -0.0002(14) C10 0.0515(18) 0.0422(18) 0.0358(17) -0.0013(14) -0.0065(13) 0.0036(14) C11 0.0440(17) 0.0378(17) 0.0386(17) -0.0032(13) -0.0022(13) -0.0011(13) C12 0.0401(16) 0.0360(17) 0.0400(17) -0.0046(13) -0.0026(13) -0.0012(13) C13 0.060(2) 0.0397(19) 0.051(2) -0.0075(15) -0.0039(15) 0.0055(15) C14 0.067(2) 0.051(2) 0.057(2) -0.0142(17) 0.0059(17) 0.0073(18) C15 0.072(2) 0.061(2) 0.041(2) -0.0159(17) 0.0023(16) 0.0041(19) C16 0.064(2) 0.055(2) 0.0385(18) -0.0056(15) -0.0034(15) 0.0042(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C10 1.226(3) . ? N1 C10 1.351(4) . ? N1 C8 1.464(4) . ? N1 H1 0.8600 . ? N2 C7 1.382(3) . ? N2 C12 1.441(4) . ? N2 C8 1.455(3) . ? N3 C7 1.296(4) . ? N3 C6 1.413(4) . ? C1 C2 1.367(4) . ? C1 C6 1.396(4) . ? C1 H1A 0.9300 . ? C2 C3 1.385(4) . ? C2 H2 0.9300 . ? C3 C4 1.388(4) . ? C3 H3 0.9300 . ? C4 C5 1.386(4) . ? C4 H4 0.9300 . ? C5 C6 1.383(4) . ? C5 C8 1.495(4) . ? C7 C9 1.494(4) . ? C8 H8 0.9800 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.493(4) . ? C11 C12 1.388(4) . ? C11 C16 1.394(4) . ? C12 C13 1.386(4) . ? C13 C14 1.376(4) . ? C13 H13 0.9300 . ? C14 C15 1.379(5) . ? C14 H14 0.9300 . ? C15 C16 1.367(5) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C10 N1 C8 120.6(2) . . ? C10 N1 H1 119.7 . . ? C8 N1 H1 119.7 . . ? C7 N2 C12 121.5(2) . . ? C7 N2 C8 119.4(2) . . ? C12 N2 C8 111.3(2) . . ? C7 N3 C6 118.0(2) . . ? C2 C1 C6 120.5(3) . . ? C2 C1 H1A 119.7 . . ? C6 C1 H1A 119.7 . . ? C1 C2 C3 120.5(3) . . ? C1 C2 H2 119.8 . . ? C3 C2 H2 119.8 . . ? C2 C3 C4 119.5(3) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C5 C4 C3 120.2(3) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C6 C5 C4 120.1(3) . . ? C6 C5 C8 118.3(2) . . ? C4 C5 C8 121.6(3) . . ? C5 C6 C1 119.3(3) . . ? C5 C6 N3 122.3(3) . . ? C1 C6 N3 118.4(3) . . ? N3 C7 N2 123.5(3) . . ? N3 C7 C9 117.5(3) . . ? N2 C7 C9 119.0(3) . . ? N2 C8 N1 108.8(2) . . ? N2 C8 C5 110.9(2) . . ? N1 C8 C5 111.8(2) . . ? N2 C8 H8 108.4 . . ? N1 C8 H8 108.4 . . ? C5 C8 H8 108.4 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O1 C10 N1 122.8(3) . . ? O1 C10 C11 122.5(3) . . ? N1 C10 C11 114.7(3) . . ? C12 C11 C16 119.0(3) . . ? C12 C11 C10 120.9(3) . . ? C16 C11 C10 120.1(3) . . ? C13 C12 C11 120.9(3) . . ? C13 C12 N2 121.8(3) . . ? C11 C12 N2 117.3(2) . . ? C14 C13 C12 118.9(3) . . ? C14 C13 H13 120.6 . . ? C12 C13 H13 120.6 . . ? C13 C14 C15 120.7(3) . . ? C13 C14 H14 119.6 . . ? C15 C14 H14 119.6 . . ? C16 C15 C14 120.5(3) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C15 C16 C11 120.0(3) . . ? C15 C16 H16 120.0 . . ? C11 C16 H16 120.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -1.0(5) . . . . ? C1 C2 C3 C4 1.2(5) . . . . ? C2 C3 C4 C5 0.2(5) . . . . ? C3 C4 C5 C6 -2.0(4) . . . . ? C3 C4 C5 C8 176.1(3) . . . . ? C4 C5 C6 C1 2.2(4) . . . . ? C8 C5 C6 C1 -175.9(3) . . . . ? C4 C5 C6 N3 -178.3(3) . . . . ? C8 C5 C6 N3 3.5(4) . . . . ? C2 C1 C6 C5 -0.8(4) . . . . ? C2 C1 C6 N3 179.8(3) . . . . ? C7 N3 C6 C5 10.2(4) . . . . ? C7 N3 C6 C1 -170.3(3) . . . . ? C6 N3 C7 N2 -1.4(4) . . . . ? C6 N3 C7 C9 177.2(2) . . . . ? C12 N2 C7 N3 -167.7(3) . . . . ? C8 N2 C7 N3 -21.2(4) . . . . ? C12 N2 C7 C9 13.7(4) . . . . ? C8 N2 C7 C9 160.2(2) . . . . ? C7 N2 C8 N1 -91.3(3) . . . . ? C12 N2 C8 N1 58.3(3) . . . . ? C7 N2 C8 C5 32.0(3) . . . . ? C12 N2 C8 C5 -178.3(2) . . . . ? C10 N1 C8 N2 -46.8(3) . . . . ? C10 N1 C8 C5 -169.6(3) . . . . ? C6 C5 C8 N2 -23.2(4) . . . . ? C4 C5 C8 N2 158.6(3) . . . . ? C6 C5 C8 N1 98.3(3) . . . . ? C4 C5 C8 N1 -79.8(3) . . . . ? C8 N1 C10 O1 -171.4(3) . . . . ? C8 N1 C10 C11 10.5(4) . . . . ? O1 C10 C11 C12 -163.5(3) . . . . ? N1 C10 C11 C12 14.7(4) . . . . ? O1 C10 C11 C16 14.6(5) . . . . ? N1 C10 C11 C16 -167.3(3) . . . . ? C16 C11 C12 C13 2.4(4) . . . . ? C10 C11 C12 C13 -179.5(3) . . . . ? C16 C11 C12 N2 -178.7(3) . . . . ? C10 C11 C12 N2 -0.6(4) . . . . ? C7 N2 C12 C13 -68.9(4) . . . . ? C8 N2 C12 C13 142.1(3) . . . . ? C7 N2 C12 C11 112.2(3) . . . . ? C8 N2 C12 C11 -36.7(3) . . . . ? C11 C12 C13 C14 -2.4(4) . . . . ? N2 C12 C13 C14 178.8(3) . . . . ? C12 C13 C14 C15 0.8(5) . . . . ? C13 C14 C15 C16 0.9(5) . . . . ? C14 C15 C16 C11 -0.9(5) . . . . ? C12 C11 C16 C15 -0.7(5) . . . . ? C10 C11 C16 C15 -178.9(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 N3 0.86 2.18 3.025(3) 165.8 3 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.337 _refine_diff_density_min -0.285 _refine_diff_density_rms 0.088 _database_code_depnum_ccdc_archive 'CCDC 907665' ####################################################################### # # 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_mo_20111101a_0m #TrackingRef '3ae.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H22 N4 O' _chemical_formula_sum 'C19 H22 N4 O' _chemical_formula_weight 322.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 9.666(10) _cell_length_b 10.849(11) _cell_length_c 15.997(16) _cell_angle_alpha 90.00 _cell_angle_beta 100.738(19) _cell_angle_gamma 90.00 _cell_volume 1648(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2358 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 26.57 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.299 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9811 _exptl_absorpt_correction_T_max 0.9876 _exptl_absorpt_process_details 'SADABS (Bruker, 2002)' _diffrn_ambient_temperature 298(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 'Bruker APEX II area-detector diffractometer' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10051 _diffrn_reflns_av_R_equivalents 0.0403 _diffrn_reflns_av_sigmaI/netI 0.0429 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3039 _reflns_number_gt 2008 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (Bruker, 2002)' _computing_publication_material 'SHELXL-97 (Bruker, 2002)' _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^)+(0.1208P)^2^+0.1288P] 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 3039 _refine_ls_number_parameters 220 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0896 _refine_ls_R_factor_gt 0.0566 _refine_ls_wR_factor_ref 0.2063 _refine_ls_wR_factor_gt 0.1773 _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_restrained_S_all 1.101 _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 0.9337(2) 0.7033(2) 0.14947(13) 0.0807(7) Uani 1 1 d . . . N1 N 0.5408(2) 0.7653(2) 0.03592(13) 0.0516(6) Uani 1 1 d . . . H1 H 0.4512 0.7593 0.0326 0.062 Uiso 1 1 calc R . . N2 N 0.7398(2) 0.8156(2) 0.13321(13) 0.0523(6) Uani 1 1 d . . . H2A H 0.7629 0.8451 0.1838 0.063 Uiso 1 1 calc R . . N3 N 0.66628(19) 1.11446(19) 0.10606(12) 0.0470(5) Uani 1 1 d . . . N4 N 0.8213(2) 1.1003(3) 0.23208(14) 0.0763(8) Uani 1 1 d . . . H4A H 0.7432 1.0892 0.2531 0.114 Uiso 1 1 d R . . H4B H 0.8723 1.1603 0.2607 0.114 Uiso 1 1 d R . . C1 C 0.6134(2) 0.6797(2) 0.00117(15) 0.0456(6) Uani 1 1 d . . . C2 C 0.5510(3) 0.6068(3) -0.06532(17) 0.0608(7) Uani 1 1 d . . . H2 H 0.4560 0.6170 -0.0883 0.073 Uiso 1 1 calc R . . C3 C 0.6260(3) 0.5211(3) -0.0973(2) 0.0694(8) Uani 1 1 d . . . H3 H 0.5823 0.4731 -0.1429 0.083 Uiso 1 1 calc R . . C4 C 0.7635(3) 0.5029(3) -0.06494(19) 0.0673(8) Uani 1 1 d . . . H4 H 0.8152 0.4442 -0.0884 0.081 Uiso 1 1 calc R . . C5 C 0.8245(3) 0.5712(3) 0.00210(17) 0.0583(7) Uani 1 1 d . . . H5 H 0.9184 0.5570 0.0262 0.070 Uiso 1 1 calc R . . C6 C 0.7531(2) 0.6596(2) 0.03509(15) 0.0454(6) Uani 1 1 d . . . C7 C 0.8180(2) 0.7273(2) 0.10962(15) 0.0502(6) Uani 1 1 d . . . C8 C 0.6170(2) 0.8647(2) 0.07774(16) 0.0488(6) Uani 1 1 d . . . H8 H 0.6472 0.9187 0.0354 0.059 Uiso 1 1 calc R . . C9 C 0.5323(2) 0.9372(2) 0.12841(14) 0.0453(6) Uani 1 1 d . . . C10 C 0.4252(3) 0.8856(3) 0.16083(17) 0.0556(7) Uani 1 1 d . . . H10 H 0.4052 0.8023 0.1519 0.067 Uiso 1 1 calc R . . C11 C 0.3479(3) 0.9534(3) 0.20567(18) 0.0654(8) Uani 1 1 d . . . H11 H 0.2749 0.9169 0.2273 0.079 Uiso 1 1 calc R . . C12 C 0.3761(3) 1.0739(3) 0.21921(18) 0.0670(8) Uani 1 1 d . . . H12 H 0.3227 1.1207 0.2502 0.080 Uiso 1 1 calc R . . C13 C 0.4820(3) 1.1271(3) 0.18782(17) 0.0566(7) Uani 1 1 d . . . H13 H 0.5006 1.2105 0.1972 0.068 Uiso 1 1 calc R . . C14 C 0.5619(2) 1.0600(2) 0.14257(14) 0.0447(6) Uani 1 1 d . . . C15 C 0.7862(3) 1.1329(2) 0.15033(15) 0.0500(6) Uani 1 1 d . . . C16 C 0.8985(3) 1.1872(3) 0.11177(17) 0.0607(7) Uani 1 1 d . . . C17 C 0.8533(3) 1.1981(4) 0.01713(18) 0.0777(9) Uani 1 1 d . . . H17A H 0.8286 1.1182 -0.0067 0.117 Uiso 1 1 calc R . . H17B H 0.9292 1.2315 -0.0069 0.117 Uiso 1 1 calc R . . H17C H 0.7732 1.2518 0.0044 0.117 Uiso 1 1 calc R . . C18 C 0.9328(4) 1.3139(4) 0.1489(2) 0.0913(11) Uani 1 1 d . . . H18A H 0.8491 1.3636 0.1395 0.137 Uiso 1 1 calc R . . H18B H 1.0028 1.3516 0.1219 0.137 Uiso 1 1 calc R . . H18C H 0.9682 1.3069 0.2089 0.137 Uiso 1 1 calc R . . C19 C 1.0250(3) 1.1052(4) 0.1299(3) 0.1040(13) Uani 1 1 d . . . H19A H 1.0608 1.1038 0.1901 0.156 Uiso 1 1 calc R . . H19B H 1.0963 1.1361 0.1009 0.156 Uiso 1 1 calc R . . H19C H 0.9992 1.0233 0.1105 0.156 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 0.0522(12) 0.1106(17) 0.0672(13) -0.0193(11) -0.0206(9) 0.0351(11) N1 0.0337(10) 0.0603(13) 0.0554(12) -0.0073(10) -0.0056(9) 0.0063(9) N2 0.0399(11) 0.0645(14) 0.0468(11) -0.0067(10) -0.0071(9) 0.0110(10) N3 0.0373(11) 0.0544(13) 0.0448(11) 0.0003(9) -0.0036(8) 0.0032(9) N4 0.0500(13) 0.124(2) 0.0472(13) 0.0150(13) -0.0101(10) -0.0222(14) C1 0.0416(12) 0.0490(15) 0.0438(13) 0.0033(10) 0.0017(10) 0.0041(11) C2 0.0494(15) 0.0676(18) 0.0585(16) -0.0090(13) -0.0079(12) 0.0016(13) C3 0.076(2) 0.067(2) 0.0606(17) -0.0144(14) 0.0012(14) 0.0043(15) C4 0.0696(18) 0.0676(19) 0.0622(18) -0.0109(14) 0.0062(14) 0.0194(15) C5 0.0494(14) 0.0670(18) 0.0570(16) 0.0017(13) 0.0058(12) 0.0151(13) C6 0.0434(12) 0.0486(14) 0.0422(12) 0.0050(10) 0.0028(10) 0.0043(10) C7 0.0337(12) 0.0686(17) 0.0450(13) 0.0043(12) -0.0011(10) 0.0106(11) C8 0.0406(12) 0.0539(15) 0.0479(13) -0.0008(11) -0.0025(10) 0.0051(11) C9 0.0346(11) 0.0554(15) 0.0417(12) 0.0013(11) -0.0039(9) 0.0056(10) C10 0.0448(14) 0.0623(17) 0.0570(16) 0.0036(13) 0.0026(11) 0.0027(12) C11 0.0458(15) 0.091(2) 0.0584(17) 0.0034(16) 0.0072(12) -0.0030(15) C12 0.0442(15) 0.097(2) 0.0598(17) -0.0150(16) 0.0087(12) 0.0157(15) C13 0.0487(15) 0.0607(17) 0.0558(15) -0.0095(13) -0.0026(12) 0.0117(12) C14 0.0321(11) 0.0577(16) 0.0392(12) 0.0002(11) -0.0066(9) 0.0069(10) C15 0.0452(13) 0.0560(16) 0.0437(13) 0.0034(11) -0.0050(10) 0.0037(11) C16 0.0461(14) 0.0759(19) 0.0560(16) 0.0084(13) -0.0012(11) -0.0014(13) C17 0.0699(19) 0.109(3) 0.0541(17) 0.0116(17) 0.0105(14) -0.0086(17) C18 0.106(3) 0.092(3) 0.073(2) 0.0046(18) 0.0082(19) -0.034(2) C19 0.055(2) 0.149(4) 0.108(3) 0.027(3) 0.0148(19) 0.025(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C7 1.208(3) . ? N1 C1 1.345(3) . ? N1 C8 1.404(3) . ? N1 H1 0.8600 . ? N2 C7 1.317(3) . ? N2 C8 1.446(3) . ? N2 H2A 0.8600 . ? N3 C15 1.257(3) . ? N3 C14 1.388(3) . ? N4 C15 1.336(3) . ? N4 H4A 0.8900 . ? N4 H4B 0.8900 . ? C1 C2 1.371(4) . ? C1 C6 1.375(3) . ? C2 C3 1.338(4) . ? C2 H2 0.9300 . ? C3 C4 1.349(4) . ? C3 H3 0.9300 . ? C4 C5 1.346(4) . ? C4 H4 0.9300 . ? C5 C6 1.346(4) . ? C5 H5 0.9300 . ? C6 C7 1.441(4) . ? C8 C9 1.480(4) . ? C8 H8 0.9800 . ? C9 C10 1.362(4) . ? C9 C14 1.373(4) . ? C10 C11 1.347(4) . ? C10 H10 0.9300 . ? C11 C12 1.345(5) . ? C11 H11 0.9300 . ? C12 C13 1.351(4) . ? C12 H12 0.9300 . ? C13 C14 1.363(4) . ? C13 H13 0.9300 . ? C15 C16 1.468(4) . ? C16 C19 1.496(5) . ? C16 C17 1.500(4) . ? C16 C18 1.509(5) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? 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 C8 117.4(2) . . ? C1 N1 H1 121.3 . . ? C8 N1 H1 121.3 . . ? C7 N2 C8 122.8(2) . . ? C7 N2 H2A 118.6 . . ? C8 N2 H2A 118.6 . . ? C15 N3 C14 119.8(2) . . ? C15 N4 H4A 109.1 . . ? C15 N4 H4B 108.9 . . ? H4A N4 H4B 109.5 . . ? N1 C1 C2 122.0(2) . . ? N1 C1 C6 119.7(2) . . ? C2 C1 C6 118.2(2) . . ? C3 C2 C1 120.4(3) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C2 C3 C4 121.3(3) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? C5 C4 C3 118.7(3) . . ? C5 C4 H4 120.7 . . ? C3 C4 H4 120.7 . . ? C6 C5 C4 121.6(3) . . ? C6 C5 H5 119.2 . . ? C4 C5 H5 119.2 . . ? C5 C6 C1 119.7(2) . . ? C5 C6 C7 120.8(2) . . ? C1 C6 C7 119.4(2) . . ? O1 C7 N2 122.0(2) . . ? O1 C7 C6 123.0(2) . . ? N2 C7 C6 115.0(2) . . ? N1 C8 N2 107.9(2) . . ? N1 C8 C9 112.0(2) . . ? N2 C8 C9 109.5(2) . . ? N1 C8 H8 109.1 . . ? N2 C8 H8 109.1 . . ? C9 C8 H8 109.1 . . ? C10 C9 C14 119.1(2) . . ? C10 C9 C8 121.8(2) . . ? C14 C9 C8 119.1(2) . . ? C11 C10 C9 121.0(3) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C12 C11 C10 120.0(3) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C11 C12 C13 120.0(3) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C12 C13 C14 120.9(3) . . ? C12 C13 H13 119.6 . . ? C14 C13 H13 119.6 . . ? C13 C14 C9 119.0(2) . . ? C13 C14 N3 121.7(2) . . ? C9 C14 N3 119.3(2) . . ? N3 C15 N4 123.3(2) . . ? N3 C15 C16 120.3(2) . . ? N4 C15 C16 116.4(2) . . ? C15 C16 C19 108.8(3) . . ? C15 C16 C17 110.9(2) . . ? C19 C16 C17 108.5(3) . . ? C15 C16 C18 109.0(3) . . ? C19 C16 C18 110.7(3) . . ? C17 C16 C18 109.0(3) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 N1 C1 C2 -155.4(3) . . . . ? C8 N1 C1 C6 27.6(3) . . . . ? N1 C1 C2 C3 -178.8(3) . . . . ? C6 C1 C2 C3 -1.8(4) . . . . ? C1 C2 C3 C4 0.7(5) . . . . ? C2 C3 C4 C5 1.4(5) . . . . ? C3 C4 C5 C6 -2.5(5) . . . . ? C4 C5 C6 C1 1.4(4) . . . . ? C4 C5 C6 C7 176.7(3) . . . . ? N1 C1 C6 C5 177.8(2) . . . . ? C2 C1 C6 C5 0.7(4) . . . . ? N1 C1 C6 C7 2.5(4) . . . . ? C2 C1 C6 C7 -174.6(2) . . . . ? C8 N2 C7 O1 165.6(3) . . . . ? C8 N2 C7 C6 -16.5(4) . . . . ? C5 C6 C7 O1 -5.4(4) . . . . ? C1 C6 C7 O1 169.8(3) . . . . ? C5 C6 C7 N2 176.7(2) . . . . ? C1 C6 C7 N2 -8.0(3) . . . . ? C1 N1 C8 N2 -47.2(3) . . . . ? C1 N1 C8 C9 -167.8(2) . . . . ? C7 N2 C8 N1 43.2(3) . . . . ? C7 N2 C8 C9 165.3(2) . . . . ? N1 C8 C9 C10 27.2(3) . . . . ? N2 C8 C9 C10 -92.4(3) . . . . ? N1 C8 C9 C14 -152.3(2) . . . . ? N2 C8 C9 C14 88.1(3) . . . . ? C14 C9 C10 C11 0.5(4) . . . . ? C8 C9 C10 C11 -178.9(2) . . . . ? C9 C10 C11 C12 -0.2(4) . . . . ? C10 C11 C12 C13 0.0(4) . . . . ? C11 C12 C13 C14 -0.3(4) . . . . ? C12 C13 C14 C9 0.7(3) . . . . ? C12 C13 C14 N3 176.6(2) . . . . ? C10 C9 C14 C13 -0.8(3) . . . . ? C8 C9 C14 C13 178.7(2) . . . . ? C10 C9 C14 N3 -176.8(2) . . . . ? C8 C9 C14 N3 2.7(3) . . . . ? C15 N3 C14 C13 83.0(3) . . . . ? C15 N3 C14 C9 -101.2(3) . . . . ? C14 N3 C15 N4 1.4(4) . . . . ? C14 N3 C15 C16 178.3(2) . . . . ? N3 C15 C16 C19 -126.6(3) . . . . ? N4 C15 C16 C19 50.5(4) . . . . ? N3 C15 C16 C17 -7.4(4) . . . . ? N4 C15 C16 C17 169.7(3) . . . . ? N3 C15 C16 C18 112.7(3) . . . . ? N4 C15 C16 C18 -70.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.339 _refine_diff_density_min -0.330 _refine_diff_density_rms 0.049 _database_code_depnum_ccdc_archive 'CCDC 907666' ####################################################################### # # 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_mo_20120729b_0m #TrackingRef '3hc.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H17 N3 O2' _chemical_formula_sum 'C19 H17 N3 O2' _chemical_formula_weight 319.36 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 5.2403(4) _cell_length_b 16.3094(12) _cell_length_c 17.8420(13) _cell_angle_alpha 90.00 _cell_angle_beta 94.9210(10) _cell_angle_gamma 90.00 _cell_volume 1519.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3758 _cell_measurement_theta_min 2.15 _cell_measurement_theta_max 27.56 _exptl_crystal_description Prsim _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.396 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9780 _exptl_absorpt_correction_T_max 0.9862 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11496 _diffrn_reflns_av_R_equivalents 0.0197 _diffrn_reflns_av_sigmaI/netI 0.0187 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2811 _reflns_number_gt 2454 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0631P)^2^+0.3232P] 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 2811 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0416 _refine_ls_R_factor_gt 0.0357 _refine_ls_wR_factor_ref 0.1073 _refine_ls_wR_factor_gt 0.1027 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _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 0.26179(17) 0.42052(6) 0.01189(5) 0.0275(2) Uani 1 1 d . . . O2 O 0.8203(2) 0.80934(6) 0.06284(6) 0.0408(3) Uani 1 1 d . . . N1 N 0.3394(2) 0.53431(6) 0.08361(6) 0.0231(2) Uani 1 1 d . . . H1A H 0.4756 0.5463 0.0623 0.028 Uiso 1 1 calc R . . N2 N 0.18663(19) 0.54431(6) 0.20585(6) 0.0223(2) Uani 1 1 d . . . N3 N 0.4953(2) 0.61059(7) 0.28968(6) 0.0279(3) Uani 1 1 d . . . C1 C -0.1414(2) 0.37438(8) 0.09938(7) 0.0263(3) Uani 1 1 d . . . H1 H -0.1331 0.3478 0.0535 0.032 Uiso 1 1 calc R . . C2 C -0.3148(3) 0.34798(9) 0.14829(8) 0.0292(3) Uani 1 1 d . . . H2 H -0.4188 0.3028 0.1363 0.035 Uiso 1 1 calc R . . C3 C -0.3322(2) 0.38960(8) 0.21550(8) 0.0283(3) Uani 1 1 d . . . H3 H -0.4520 0.3730 0.2479 0.034 Uiso 1 1 calc R . . C4 C -0.1739(2) 0.45544(8) 0.23488(8) 0.0257(3) Uani 1 1 d . . . H4 H -0.1902 0.4836 0.2796 0.031 Uiso 1 1 calc R . . C5 C 0.0101(2) 0.47967(8) 0.18738(7) 0.0215(3) Uani 1 1 d . . . C6 C 0.0211(2) 0.44013(8) 0.11785(7) 0.0220(3) Uani 1 1 d . . . C7 C 0.2149(2) 0.46415(8) 0.06581(7) 0.0214(3) Uani 1 1 d . . . C8 C 0.2457(2) 0.59097(8) 0.13917(7) 0.0219(3) Uani 1 1 d . . . H8 H 0.0885 0.6172 0.1172 0.026 Uiso 1 1 calc R . . C9 C 0.4434(2) 0.65598(7) 0.15815(7) 0.0240(3) Uani 1 1 d . . . C10 C 0.5203(3) 0.70611(8) 0.10093(8) 0.0274(3) Uani 1 1 d . . . H10 H 0.4360 0.7034 0.0530 0.033 Uiso 1 1 calc R . . C11 C 0.7227(3) 0.75996(8) 0.11579(8) 0.0296(3) Uani 1 1 d . . . C12 C 0.8436(3) 0.76526(8) 0.18819(9) 0.0321(3) Uani 1 1 d . . . H12 H 0.9807 0.8010 0.1982 0.038 Uiso 1 1 calc R . . C13 C 0.7602(3) 0.71760(8) 0.24496(8) 0.0303(3) Uani 1 1 d . . . H13 H 0.8394 0.7225 0.2934 0.036 Uiso 1 1 calc R . . C14 C 0.5587(2) 0.66191(8) 0.23106(7) 0.0252(3) Uani 1 1 d . . . C15 C 0.3266(2) 0.55397(8) 0.27494(7) 0.0237(3) Uani 1 1 d . . . C16 C 0.2864(2) 0.49317(9) 0.33525(7) 0.0269(3) Uani 1 1 d . . . H16 H 0.2170 0.4399 0.3183 0.032 Uiso 1 1 calc R . . C17 C 0.2086(3) 0.52307(11) 0.40998(8) 0.0414(4) Uani 1 1 d . . . H17A H 0.1865 0.5816 0.4163 0.050 Uiso 1 1 calc R . . H17B H 0.0922 0.4891 0.4359 0.050 Uiso 1 1 calc R . . C18 C 0.4729(3) 0.49194(10) 0.40414(8) 0.0358(3) Uani 1 1 d . . . H18A H 0.5171 0.4391 0.4266 0.043 Uiso 1 1 calc R . . H18B H 0.6113 0.5316 0.4070 0.043 Uiso 1 1 calc R . . C19 C 0.7169(4) 0.79925(10) -0.01314(9) 0.0444(4) Uani 1 1 d . . . H19A H 0.7322 0.7429 -0.0277 0.067 Uiso 1 1 calc R . . H19B H 0.8094 0.8333 -0.0454 0.067 Uiso 1 1 calc R . . H19C H 0.5396 0.8148 -0.0175 0.067 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 0.0326(5) 0.0265(5) 0.0237(5) -0.0050(4) 0.0048(4) -0.0046(4) O2 0.0480(7) 0.0305(6) 0.0437(6) 0.0042(5) 0.0037(5) -0.0137(5) N1 0.0245(5) 0.0230(5) 0.0222(6) -0.0018(4) 0.0042(4) -0.0031(4) N2 0.0231(5) 0.0237(5) 0.0197(6) -0.0015(4) 0.0008(4) 0.0000(4) N3 0.0315(6) 0.0273(6) 0.0244(6) -0.0043(5) -0.0013(5) -0.0008(5) C1 0.0264(7) 0.0277(7) 0.0239(7) -0.0008(5) -0.0030(5) -0.0017(5) C2 0.0238(6) 0.0295(7) 0.0334(7) 0.0036(6) -0.0034(5) -0.0049(5) C3 0.0200(6) 0.0336(7) 0.0313(7) 0.0078(6) 0.0031(5) 0.0009(5) C4 0.0215(6) 0.0304(7) 0.0253(7) 0.0013(5) 0.0018(5) 0.0045(5) C5 0.0188(6) 0.0228(6) 0.0221(6) 0.0018(5) -0.0020(5) 0.0037(5) C6 0.0201(6) 0.0231(6) 0.0222(7) 0.0026(5) -0.0021(5) 0.0016(5) C7 0.0219(6) 0.0231(6) 0.0184(6) 0.0012(5) -0.0024(5) 0.0009(5) C8 0.0236(6) 0.0212(6) 0.0204(6) -0.0003(5) -0.0006(5) 0.0024(5) C9 0.0249(6) 0.0193(6) 0.0275(7) -0.0032(5) 0.0007(5) 0.0030(5) C10 0.0316(7) 0.0223(6) 0.0275(7) -0.0013(5) -0.0016(5) 0.0006(5) C11 0.0321(7) 0.0193(6) 0.0377(8) -0.0012(5) 0.0045(6) -0.0013(5) C12 0.0306(7) 0.0215(6) 0.0432(8) -0.0064(6) -0.0025(6) -0.0034(5) C13 0.0329(7) 0.0249(7) 0.0318(7) -0.0070(6) -0.0055(6) 0.0012(6) C14 0.0282(7) 0.0204(6) 0.0267(7) -0.0046(5) -0.0003(5) 0.0042(5) C15 0.0244(6) 0.0261(7) 0.0206(6) -0.0048(5) 0.0011(5) 0.0048(5) C16 0.0266(6) 0.0324(7) 0.0212(7) -0.0007(5) 0.0000(5) 0.0005(5) C17 0.0424(8) 0.0577(10) 0.0255(8) -0.0019(7) 0.0099(6) 0.0021(7) C18 0.0335(7) 0.0493(9) 0.0234(7) 0.0048(6) -0.0038(6) -0.0032(7) C19 0.0592(11) 0.0352(8) 0.0392(9) 0.0065(7) 0.0070(8) -0.0097(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C7 1.2382(15) . ? O2 C11 1.3730(17) . ? O2 C19 1.425(2) . ? N1 C7 1.3417(16) . ? N1 C8 1.4702(15) . ? N1 H1A 0.8600 . ? N2 C15 1.3882(16) . ? N2 C5 1.4223(16) . ? N2 C8 1.4676(16) . ? N3 C15 1.2897(17) . ? N3 C14 1.4017(17) . ? C1 C2 1.3818(19) . ? C1 C6 1.3912(18) . ? C1 H1 0.9300 . ? C2 C3 1.388(2) . ? C2 H2 0.9300 . ? C3 C4 1.3828(19) . ? C3 H3 0.9300 . ? C4 C5 1.3945(18) . ? C4 H4 0.9300 . ? C5 C6 1.4036(18) . ? C6 C7 1.4861(17) . ? C8 C9 1.5006(18) . ? C8 H8 0.9800 . ? C9 C14 1.3900(18) . ? C9 C10 1.3941(19) . ? C10 C11 1.3850(19) . ? C10 H10 0.9300 . ? C11 C12 1.392(2) . ? C12 C13 1.377(2) . ? C12 H12 0.9300 . ? C13 C14 1.3987(19) . ? C13 H13 0.9300 . ? C15 C16 1.4914(19) . ? C16 C18 1.5034(19) . ? C16 C17 1.5085(18) . ? C16 H16 0.9800 . ? C17 C18 1.487(2) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? 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 C11 O2 C19 116.94(11) . . ? C7 N1 C8 120.78(10) . . ? C7 N1 H1A 119.6 . . ? C8 N1 H1A 119.6 . . ? C15 N2 C5 124.99(10) . . ? C15 N2 C8 121.93(10) . . ? C5 N2 C8 112.00(9) . . ? C15 N3 C14 118.53(11) . . ? C2 C1 C6 120.86(12) . . ? C2 C1 H1 119.6 . . ? C6 C1 H1 119.6 . . ? C1 C2 C3 119.27(12) . . ? C1 C2 H2 120.4 . . ? C3 C2 H2 120.4 . . ? C4 C3 C2 120.89(12) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 C5 119.97(12) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C4 C5 C6 119.33(12) . . ? C4 C5 N2 122.62(11) . . ? C6 C5 N2 118.05(10) . . ? C1 C6 C5 119.54(11) . . ? C1 C6 C7 119.49(11) . . ? C5 C6 C7 120.86(11) . . ? O1 C7 N1 123.30(11) . . ? O1 C7 C6 121.72(11) . . ? N1 C7 C6 114.93(11) . . ? N2 C8 N1 109.06(10) . . ? N2 C8 C9 111.90(10) . . ? N1 C8 C9 109.41(10) . . ? N2 C8 H8 108.8 . . ? N1 C8 H8 108.8 . . ? C9 C8 H8 108.8 . . ? C14 C9 C10 120.98(12) . . ? C14 C9 C8 119.78(11) . . ? C10 C9 C8 119.11(11) . . ? C11 C10 C9 119.77(13) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? O2 C11 C10 124.37(13) . . ? O2 C11 C12 115.81(12) . . ? C10 C11 C12 119.81(13) . . ? C13 C12 C11 119.97(13) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C14 121.23(13) . . ? C12 C13 H13 119.4 . . ? C14 C13 H13 119.4 . . ? C9 C14 C13 118.17(12) . . ? C9 C14 N3 123.02(12) . . ? C13 C14 N3 118.64(12) . . ? N3 C15 N2 124.27(12) . . ? N3 C15 C16 117.76(11) . . ? N2 C15 C16 117.94(11) . . ? C15 C16 C18 118.46(12) . . ? C15 C16 C17 119.24(12) . . ? C18 C16 C17 59.18(9) . . ? C15 C16 H16 116.0 . . ? C18 C16 H16 116.0 . . ? C17 C16 H16 116.0 . . ? C18 C17 C16 60.24(9) . . ? C18 C17 H17A 117.7 . . ? C16 C17 H17A 117.7 . . ? C18 C17 H17B 117.7 . . ? C16 C17 H17B 117.7 . . ? H17A C17 H17B 114.9 . . ? C17 C18 C16 60.58(9) . . ? C17 C18 H18A 117.7 . . ? C16 C18 H18A 117.7 . . ? C17 C18 H18B 117.7 . . ? C16 C18 H18B 117.7 . . ? H18A C18 H18B 114.8 . . ? O2 C19 H19A 109.5 . . ? O2 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O2 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 2.2(2) . . . . ? C1 C2 C3 C4 -1.8(2) . . . . ? C2 C3 C4 C5 -1.43(19) . . . . ? C3 C4 C5 C6 4.19(18) . . . . ? C3 C4 C5 N2 -176.90(11) . . . . ? C15 N2 C5 C4 46.36(17) . . . . ? C8 N2 C5 C4 -145.37(12) . . . . ? C15 N2 C5 C6 -134.72(12) . . . . ? C8 N2 C5 C6 33.56(14) . . . . ? C2 C1 C6 C5 0.59(19) . . . . ? C2 C1 C6 C7 176.76(12) . . . . ? C4 C5 C6 C1 -3.77(18) . . . . ? N2 C5 C6 C1 177.27(11) . . . . ? C4 C5 C6 C7 -179.89(11) . . . . ? N2 C5 C6 C7 1.15(17) . . . . ? C8 N1 C7 O1 168.77(12) . . . . ? C8 N1 C7 C6 -13.68(16) . . . . ? C1 C6 C7 O1 -10.61(18) . . . . ? C5 C6 C7 O1 165.51(11) . . . . ? C1 C6 C7 N1 171.80(11) . . . . ? C5 C6 C7 N1 -12.08(17) . . . . ? C15 N2 C8 N1 113.19(12) . . . . ? C5 N2 C8 N1 -55.50(12) . . . . ? C15 N2 C8 C9 -7.99(15) . . . . ? C5 N2 C8 C9 -176.68(10) . . . . ? C7 N1 C8 N2 47.40(14) . . . . ? C7 N1 C8 C9 170.09(11) . . . . ? N2 C8 C9 C14 4.41(16) . . . . ? N1 C8 C9 C14 -116.56(12) . . . . ? N2 C8 C9 C10 -179.75(10) . . . . ? N1 C8 C9 C10 59.27(15) . . . . ? C14 C9 C10 C11 3.11(19) . . . . ? C8 C9 C10 C11 -172.67(12) . . . . ? C19 O2 C11 C10 -4.9(2) . . . . ? C19 O2 C11 C12 173.95(13) . . . . ? C9 C10 C11 O2 177.12(12) . . . . ? C9 C10 C11 C12 -1.7(2) . . . . ? O2 C11 C12 C13 -179.54(12) . . . . ? C10 C11 C12 C13 -0.6(2) . . . . ? C11 C12 C13 C14 1.6(2) . . . . ? C10 C9 C14 C13 -2.15(18) . . . . ? C8 C9 C14 C13 173.61(11) . . . . ? C10 C9 C14 N3 -177.29(11) . . . . ? C8 C9 C14 N3 -1.53(18) . . . . ? C12 C13 C14 C9 -0.22(19) . . . . ? C12 C13 C14 N3 175.14(12) . . . . ? C15 N3 C14 C9 1.74(18) . . . . ? C15 N3 C14 C13 -173.38(12) . . . . ? C14 N3 C15 N2 -5.55(18) . . . . ? C14 N3 C15 C16 172.13(11) . . . . ? C5 N2 C15 N3 176.41(11) . . . . ? C8 N2 C15 N3 9.24(18) . . . . ? C5 N2 C15 C16 -1.27(17) . . . . ? C8 N2 C15 C16 -168.44(10) . . . . ? N3 C15 C16 C18 -10.41(18) . . . . ? N2 C15 C16 C18 167.43(12) . . . . ? N3 C15 C16 C17 58.23(16) . . . . ? N2 C15 C16 C17 -123.94(13) . . . . ? C15 C16 C17 C18 -107.58(14) . . . . ? C15 C16 C18 C17 108.88(14) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A O1 0.86 2.06 2.9025(13) 165.7 3_665 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.205 _refine_diff_density_min -0.185 _refine_diff_density_rms 0.042 _database_code_depnum_ccdc_archive 'CCDC 907668' ####################################################################### # # 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_mo_20120422a_0m #TrackingRef '4af.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H26 N4 O2' _chemical_formula_weight 414.50 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.692(4) _cell_length_b 11.309(4) _cell_length_c 17.125(6) _cell_angle_alpha 90.00 _cell_angle_beta 91.039(8) _cell_angle_gamma 90.00 _cell_volume 2264.0(13) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.216 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9782 _exptl_absorpt_correction_T_max 0.9882 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12799 _diffrn_reflns_av_R_equivalents 0.0750 _diffrn_reflns_av_sigmaI/netI 0.0789 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 25.10 _reflns_number_total 4004 _reflns_number_gt 2246 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1339P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.012(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4004 _refine_ls_number_parameters 281 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1318 _refine_ls_R_factor_gt 0.0729 _refine_ls_wR_factor_ref 0.2386 _refine_ls_wR_factor_gt 0.2025 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 N3 N 0.1307(2) 0.5957(2) 1.07331(16) 0.0421(7) Uani 1 1 d . . . C14 C 0.1231(3) 0.6580(3) 1.00232(19) 0.0414(8) Uani 1 1 d . . . C9 C 0.1399(3) 0.6035(3) 0.92979(19) 0.0406(8) Uani 1 1 d . . . O1 O 0.44539(19) 0.3676(2) 0.85047(16) 0.0625(8) Uani 1 1 d . . . N1 N 0.2960(2) 0.4723(3) 0.89540(17) 0.0483(8) Uani 1 1 d . . . H1 H 0.3365 0.5357 0.8971 0.058 Uiso 1 1 calc R . . N2 N 0.1077(2) 0.4112(2) 0.86829(17) 0.0459(8) Uani 1 1 d . . . H2 H 0.0452 0.4400 0.8491 0.055 Uiso 1 1 calc R . . C15 C 0.2287(3) 0.5833(3) 1.10811(19) 0.0383(8) Uani 1 1 d . . . C6 C 0.2630(3) 0.2753(3) 0.85378(19) 0.0425(8) Uani 1 1 d . . . N4 N 0.3278(2) 0.6253(3) 1.08180(17) 0.0525(8) Uani 1 1 d . . . H4A H 0.3405 0.5948 1.0348 0.079 Uiso 1 1 d R . . H4B H 0.3841 0.6043 1.1146 0.079 Uiso 1 1 d R . . C7 C 0.3430(3) 0.3739(3) 0.8675(2) 0.0451(9) Uani 1 1 d . . . C16 C 0.2318(3) 0.5205(3) 1.1845(2) 0.0415(8) Uani 1 1 d . . . C1 C 0.1458(3) 0.3000(3) 0.8487(2) 0.0438(8) Uani 1 1 d . . . C8 C 0.1789(3) 0.4771(3) 0.9231(2) 0.0423(8) Uani 1 1 d . . . H8 H 0.1756 0.4394 0.9745 0.051 Uiso 1 1 calc R . . C10 C 0.1212(3) 0.6690(3) 0.8618(2) 0.0494(9) Uani 1 1 d . . . H10 H 0.1317 0.6331 0.8136 0.059 Uiso 1 1 calc R . . C12 C 0.0719(3) 0.8383(3) 0.9341(2) 0.0597(10) Uani 1 1 d . . . H12 H 0.0498 0.9172 0.9358 0.072 Uiso 1 1 calc R . . C2 C 0.0717(3) 0.2123(3) 0.8209(2) 0.0543(10) Uani 1 1 d . . . H2A H -0.0060 0.2284 0.8151 0.065 Uiso 1 1 calc R . . C3 C 0.1128(3) 0.1026(3) 0.8021(2) 0.0589(11) Uani 1 1 d . . . H3 H 0.0628 0.0453 0.7826 0.071 Uiso 1 1 calc R . . C13 C 0.0883(3) 0.7758(3) 1.0028(2) 0.0508(10) Uani 1 1 d . . . H13 H 0.0758 0.8132 1.0503 0.061 Uiso 1 1 calc R . . C5 C 0.3017(3) 0.1622(3) 0.8357(2) 0.0545(10) Uani 1 1 d . . . H5 H 0.3793 0.1451 0.8401 0.065 Uiso 1 1 calc R . . C21 C 0.3095(3) 0.5485(3) 1.2432(2) 0.0533(10) Uani 1 1 d . . . H21 H 0.3646 0.6061 1.2347 0.064 Uiso 1 1 calc R . . C11 C 0.0878(3) 0.7852(3) 0.8644(2) 0.0558(10) Uani 1 1 d . . . H11 H 0.0761 0.8273 0.8183 0.067 Uiso 1 1 calc R . . C18 C 0.1481(4) 0.3784(3) 1.2698(3) 0.0661(12) Uani 1 1 d . . . H18 H 0.0930 0.3209 1.2786 0.079 Uiso 1 1 calc R . . C17 C 0.1514(3) 0.4341(3) 1.1993(2) 0.0518(10) Uani 1 1 d . . . H17 H 0.0985 0.4135 1.1604 0.062 Uiso 1 1 calc R . . C20 C 0.3064(4) 0.4921(4) 1.3142(2) 0.0673(12) Uani 1 1 d . . . H20 H 0.3593 0.5118 1.3533 0.081 Uiso 1 1 calc R . . C19 C 0.2254(4) 0.4065(4) 1.3277(3) 0.0691(12) Uani 1 1 d . . . H19 H 0.2233 0.3681 1.3758 0.083 Uiso 1 1 calc R . . C4 C 0.2273(4) 0.0761(3) 0.8116(2) 0.0625(11) Uani 1 1 d . . . H4 H 0.2537 0.0001 0.8016 0.075 Uiso 1 1 calc R . . O2 O 0.5744(2) 0.3006(3) 0.07263(19) 0.0772(9) Uani 1 1 d . . . C25 C 0.4549(5) 0.3170(5) 0.0724(4) 0.120(2) Uani 1 1 d . . . H25A H 0.4353 0.3778 0.1098 0.144 Uiso 1 1 calc R . . H25B H 0.4287 0.3426 0.0211 0.144 Uiso 1 1 calc R . . C23 C 0.4903(7) 0.1294(7) 0.1125(6) 0.192(4) Uani 1 1 d . . . H23A H 0.4866 0.0609 0.0785 0.230 Uiso 1 1 calc R . . H23B H 0.4817 0.1031 0.1660 0.230 Uiso 1 1 calc R . . C22 C 0.5982(5) 0.1898(5) 0.1040(4) 0.114(2) Uani 1 1 d . . . H22A H 0.6368 0.1978 0.1543 0.136 Uiso 1 1 calc R . . H22B H 0.6474 0.1457 0.0695 0.136 Uiso 1 1 calc R . . C24 C 0.4018(6) 0.2120(8) 0.0918(7) 0.212(6) Uani 1 1 d . . . H24A H 0.3569 0.1825 0.0477 0.255 Uiso 1 1 calc R . . H24B H 0.3513 0.2239 0.1354 0.255 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 N3 0.0299(15) 0.0493(17) 0.0468(17) 0.0055(13) -0.0056(12) 0.0005(12) C14 0.0254(16) 0.048(2) 0.051(2) 0.0011(17) -0.0064(14) 0.0016(14) C9 0.0283(17) 0.0434(19) 0.050(2) 0.0032(16) -0.0064(14) 0.0006(14) O1 0.0277(14) 0.0752(18) 0.0845(19) -0.0143(15) -0.0029(12) 0.0033(12) N1 0.0303(15) 0.0482(17) 0.066(2) -0.0104(15) -0.0058(13) -0.0043(13) N2 0.0315(15) 0.0432(16) 0.0629(19) -0.0034(14) -0.0058(13) 0.0020(13) C15 0.0281(17) 0.0389(17) 0.048(2) -0.0020(15) -0.0011(14) 0.0022(14) C6 0.0339(19) 0.048(2) 0.046(2) 0.0005(16) 0.0006(15) -0.0002(15) N4 0.0295(16) 0.069(2) 0.0590(19) 0.0033(16) -0.0052(13) -0.0031(14) C7 0.0298(18) 0.057(2) 0.048(2) -0.0015(18) -0.0080(14) 0.0034(16) C16 0.0306(18) 0.0406(18) 0.053(2) 0.0004(16) -0.0019(15) 0.0043(15) C1 0.0336(18) 0.046(2) 0.051(2) -0.0018(16) 0.0009(15) -0.0013(15) C8 0.0321(18) 0.0468(19) 0.048(2) 0.0000(16) -0.0017(14) -0.0004(15) C10 0.047(2) 0.057(2) 0.044(2) 0.0030(18) -0.0012(16) -0.0020(18) C12 0.061(3) 0.048(2) 0.069(3) 0.001(2) -0.011(2) 0.0152(19) C2 0.039(2) 0.053(2) 0.071(3) -0.0077(19) -0.0028(18) -0.0069(17) C3 0.053(2) 0.051(2) 0.073(3) -0.004(2) 0.003(2) -0.0114(19) C13 0.048(2) 0.048(2) 0.056(2) -0.0053(18) -0.0068(17) 0.0049(17) C5 0.045(2) 0.062(2) 0.057(2) -0.0004(19) 0.0047(17) 0.0099(19) C21 0.042(2) 0.060(2) 0.058(2) 0.0135(19) -0.0075(17) -0.0059(17) C11 0.056(2) 0.053(2) 0.058(3) 0.015(2) -0.0125(18) -0.0052(18) C18 0.054(2) 0.054(2) 0.090(3) 0.020(2) 0.003(2) -0.004(2) C17 0.041(2) 0.052(2) 0.063(2) 0.0100(19) -0.0072(17) -0.0037(17) C20 0.055(3) 0.081(3) 0.065(3) 0.014(2) -0.015(2) -0.003(2) C19 0.058(3) 0.080(3) 0.069(3) 0.030(2) -0.001(2) 0.011(2) C4 0.065(3) 0.044(2) 0.079(3) -0.006(2) 0.005(2) 0.006(2) O2 0.0571(19) 0.076(2) 0.098(2) 0.0226(17) -0.0044(16) -0.0092(15) C25 0.059(3) 0.113(4) 0.187(6) 0.042(5) -0.011(3) 0.001(3) C23 0.128(7) 0.107(5) 0.341(14) 0.068(7) 0.017(8) -0.040(5) C22 0.088(4) 0.088(4) 0.164(6) 0.041(4) 0.000(4) -0.003(3) C24 0.070(5) 0.170(8) 0.396(16) 0.132(9) -0.012(7) -0.035(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N3 C15 1.289(4) . ? N3 C14 1.406(4) . ? C14 C13 1.393(5) . ? C14 C9 1.403(5) . ? C9 C10 1.394(5) . ? C9 C8 1.505(5) . ? O1 C7 1.240(4) . ? N1 C7 1.333(4) . ? N1 C8 1.458(4) . ? N1 H1 0.8600 . ? N2 C1 1.378(4) . ? N2 C8 1.449(4) . ? N2 H2 0.8600 . ? C15 N4 1.339(4) . ? C15 C16 1.488(5) . ? C6 C5 1.393(5) . ? C6 C1 1.400(4) . ? C6 C7 1.471(5) . ? N4 H4A 0.8900 . ? N4 H4B 0.8900 . ? C16 C21 1.380(5) . ? C16 C17 1.383(5) . ? C1 C2 1.395(5) . ? C8 H8 0.9800 . ? C10 C11 1.372(5) . ? C10 H10 0.9300 . ? C12 C11 1.352(5) . ? C12 C13 1.383(5) . ? C12 H12 0.9300 . ? C2 C3 1.371(5) . ? C2 H2A 0.9300 . ? C3 C4 1.379(6) . ? C3 H3 0.9300 . ? C13 H13 0.9300 . ? C5 C4 1.364(5) . ? C5 H5 0.9300 . ? C21 C20 1.374(5) . ? C21 H21 0.9300 . ? C11 H11 0.9300 . ? C18 C17 1.363(5) . ? C18 C19 1.368(6) . ? C18 H18 0.9300 . ? C17 H17 0.9300 . ? C20 C19 1.377(6) . ? C20 H20 0.9300 . ? C19 H19 0.9300 . ? C4 H4 0.9300 . ? O2 C22 1.389(6) . ? O2 C25 1.410(6) . ? C25 C24 1.384(8) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C23 C24 1.434(9) . ? C23 C22 1.445(9) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? 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 C15 N3 C14 119.7(3) . . ? C13 C14 C9 118.1(3) . . ? C13 C14 N3 119.2(3) . . ? C9 C14 N3 122.5(3) . . ? C10 C9 C14 118.9(3) . . ? C10 C9 C8 118.9(3) . . ? C14 C9 C8 122.1(3) . . ? C7 N1 C8 122.9(3) . . ? C7 N1 H1 118.5 . . ? C8 N1 H1 118.5 . . ? C1 N2 C8 116.2(3) . . ? C1 N2 H2 121.9 . . ? C8 N2 H2 121.9 . . ? N3 C15 N4 125.0(3) . . ? N3 C15 C16 117.7(3) . . ? N4 C15 C16 117.2(3) . . ? C5 C6 C1 119.4(3) . . ? C5 C6 C7 121.6(3) . . ? C1 C6 C7 118.5(3) . . ? C15 N4 H4A 109.0 . . ? C15 N4 H4B 109.1 . . ? H4A N4 H4B 109.5 . . ? O1 C7 N1 122.6(3) . . ? O1 C7 C6 122.1(3) . . ? N1 C7 C6 115.1(3) . . ? C21 C16 C17 118.0(3) . . ? C21 C16 C15 122.5(3) . . ? C17 C16 C15 119.5(3) . . ? N2 C1 C2 122.0(3) . . ? N2 C1 C6 119.2(3) . . ? C2 C1 C6 118.8(3) . . ? N2 C8 N1 107.6(3) . . ? N2 C8 C9 111.5(3) . . ? N1 C8 C9 110.4(3) . . ? N2 C8 H8 109.1 . . ? N1 C8 H8 109.1 . . ? C9 C8 H8 109.1 . . ? C11 C10 C9 121.5(3) . . ? C11 C10 H10 119.3 . . ? C9 C10 H10 119.3 . . ? C11 C12 C13 120.3(3) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C3 C2 C1 120.3(3) . . ? C3 C2 H2A 119.8 . . ? C1 C2 H2A 119.8 . . ? C2 C3 C4 120.8(4) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C12 C13 C14 121.3(4) . . ? C12 C13 H13 119.3 . . ? C14 C13 H13 119.3 . . ? C4 C5 C6 121.0(3) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C20 C21 C16 120.8(3) . . ? C20 C21 H21 119.6 . . ? C16 C21 H21 119.6 . . ? C12 C11 C10 119.9(3) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C17 C18 C19 120.5(4) . . ? C17 C18 H18 119.8 . . ? C19 C18 H18 119.8 . . ? C18 C17 C16 121.3(3) . . ? C18 C17 H17 119.4 . . ? C16 C17 H17 119.4 . . ? C19 C20 C21 120.3(4) . . ? C19 C20 H20 119.9 . . ? C21 C20 H20 119.9 . . ? C18 C19 C20 119.3(4) . . ? C18 C19 H19 120.4 . . ? C20 C19 H19 120.4 . . ? C5 C4 C3 119.5(4) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C22 O2 C25 108.1(4) . . ? C24 C25 O2 109.6(5) . . ? C24 C25 H25A 109.7 . . ? O2 C25 H25A 109.7 . . ? C24 C25 H25B 109.7 . . ? O2 C25 H25B 109.7 . . ? H25A C25 H25B 108.2 . . ? C24 C23 C22 107.1(6) . . ? C24 C23 H23A 110.3 . . ? C22 C23 H23A 110.3 . . ? C24 C23 H23B 110.3 . . ? C22 C23 H23B 110.3 . . ? H23A C23 H23B 108.5 . . ? O2 C22 C23 107.3(5) . . ? O2 C22 H22A 110.3 . . ? C23 C22 H22A 110.3 . . ? O2 C22 H22B 110.3 . . ? C23 C22 H22B 110.3 . . ? H22A C22 H22B 108.5 . . ? C25 C24 C23 107.1(6) . . ? C25 C24 H24A 110.3 . . ? C23 C24 H24A 110.3 . . ? C25 C24 H24B 110.3 . . ? C23 C24 H24B 110.3 . . ? H24A C24 H24B 108.6 . . ? 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 C15 N3 C14 C13 -98.9(4) . . . . ? C15 N3 C14 C9 86.7(4) . . . . ? C13 C14 C9 C10 0.0(5) . . . . ? N3 C14 C9 C10 174.6(3) . . . . ? C13 C14 C9 C8 179.2(3) . . . . ? N3 C14 C9 C8 -6.3(5) . . . . ? C14 N3 C15 N4 -0.3(5) . . . . ? C14 N3 C15 C16 177.8(3) . . . . ? C8 N1 C7 O1 -173.5(3) . . . . ? C8 N1 C7 C6 10.1(5) . . . . ? C5 C6 C7 O1 13.1(5) . . . . ? C1 C6 C7 O1 -158.4(3) . . . . ? C5 C6 C7 N1 -170.5(3) . . . . ? C1 C6 C7 N1 18.0(5) . . . . ? N3 C15 C16 C21 -147.5(3) . . . . ? N4 C15 C16 C21 30.8(5) . . . . ? N3 C15 C16 C17 29.7(5) . . . . ? N4 C15 C16 C17 -152.0(3) . . . . ? C8 N2 C1 C2 156.6(3) . . . . ? C8 N2 C1 C6 -26.0(5) . . . . ? C5 C6 C1 N2 178.6(3) . . . . ? C7 C6 C1 N2 -9.7(5) . . . . ? C5 C6 C1 C2 -4.0(5) . . . . ? C7 C6 C1 C2 167.7(3) . . . . ? C1 N2 C8 N1 49.4(4) . . . . ? C1 N2 C8 C9 170.5(3) . . . . ? C7 N1 C8 N2 -42.6(4) . . . . ? C7 N1 C8 C9 -164.4(3) . . . . ? C10 C9 C8 N2 -49.9(4) . . . . ? C14 C9 C8 N2 130.9(3) . . . . ? C10 C9 C8 N1 69.6(4) . . . . ? C14 C9 C8 N1 -109.6(3) . . . . ? C14 C9 C10 C11 0.5(5) . . . . ? C8 C9 C10 C11 -178.7(3) . . . . ? N2 C1 C2 C3 -179.9(4) . . . . ? C6 C1 C2 C3 2.7(6) . . . . ? C1 C2 C3 C4 1.2(6) . . . . ? C11 C12 C13 C14 1.0(6) . . . . ? C9 C14 C13 C12 -0.8(5) . . . . ? N3 C14 C13 C12 -175.5(3) . . . . ? C1 C6 C5 C4 1.4(5) . . . . ? C7 C6 C5 C4 -170.0(3) . . . . ? C17 C16 C21 C20 -0.2(5) . . . . ? C15 C16 C21 C20 177.1(3) . . . . ? C13 C12 C11 C10 -0.5(6) . . . . ? C9 C10 C11 C12 -0.2(5) . . . . ? C19 C18 C17 C16 -0.4(6) . . . . ? C21 C16 C17 C18 0.4(5) . . . . ? C15 C16 C17 C18 -177.0(3) . . . . ? C16 C21 C20 C19 0.1(6) . . . . ? C17 C18 C19 C20 0.3(7) . . . . ? C21 C20 C19 C18 -0.1(7) . . . . ? C6 C5 C4 C3 2.5(6) . . . . ? C2 C3 C4 C5 -3.9(6) . . . . ? C22 O2 C25 C24 -9.1(9) . . . . ? C25 O2 C22 C23 8.6(8) . . . . ? C24 C23 C22 O2 -5.0(11) . . . . ? O2 C25 C24 C23 5.8(13) . . . . ? C22 C23 C24 C25 -0.5(13) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O2 0.86 2.18 3.027(4) 167.5 3_666 N2 H2 N3 0.86 2.50 2.979(4) 115.9 3_567 N4 H4A O2 0.89 2.42 3.018(4) 125.1 3_666 N4 H4B O1 0.89 2.09 2.876(4) 146.0 3_667 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.340 _refine_diff_density_min -0.371 _refine_diff_density_rms 0.077 _database_code_depnum_ccdc_archive 'CCDC 907669'