# Electronic Supplementary Material (ESI) for CrystEngComm # 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_PhOx:2 #TrackingRef 'combined.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic 'KE14PCY13 4-HO-PhC(CN)=NOH, 2,3,5,6-Me4-pyridine-1-oxide' _chemical_formula_moiety '(C8 H6 N2 O2) (C8 H12 N2 O)' _chemical_formula_sum 'C16 H18 N4 O3' _exptl_crystal_description prism _exptl_crystal_colour colourless _diffrn_ambient_temperature 120(2) _chemical_formula_weight 314.34 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 'P n a 21' _symmetry_int_tables_number 33 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 15.4477(8) _cell_length_b 15.7463(8) _cell_length_c 6.4254(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1562.94(13) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 8006 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 33.15 _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.336 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9757 _exptl_absorpt_correction_T_max 0.9868 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_radiation_probe ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 19041 _diffrn_reflns_av_R_equivalents 0.0534 _diffrn_reflns_av_sigmaI/netI 0.0384 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 33.14 _reflns_number_total 3195 _reflns_number_gt 2848 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0700P)^2^+0.0400P] 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_number_reflns 3195 _refine_ls_number_parameters 218 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0446 _refine_ls_R_factor_gt 0.0384 _refine_ls_wR_factor_ref 0.1095 _refine_ls_wR_factor_gt 0.1039 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.082 _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 C11 C 0.41786(8) 0.30844(9) 1.0083(2) 0.0222(2) Uani 1 1 d . . . C12 C 0.41869(9) 0.22238(8) 0.9537(2) 0.0240(2) Uani 1 1 d . . . H12 H 0.3961 0.2050 0.8229 0.029 Uiso 1 1 calc R . . C13 C 0.45206(8) 0.16271(9) 1.0883(2) 0.0243(2) Uani 1 1 d . . . H13 H 0.4522 0.1044 1.0500 0.029 Uiso 1 1 calc R . . C14 C 0.48581(8) 0.18753(9) 1.2812(2) 0.0228(2) Uani 1 1 d . . . O14 O 0.51727(7) 0.12554(7) 1.40664(18) 0.0299(2) Uani 1 1 d . . . H14 H 0.5487(13) 0.1526(12) 1.518(4) 0.036 Uiso 1 1 d . . . C15 C 0.48647(9) 0.27304(8) 1.3357(2) 0.0245(3) Uani 1 1 d . . . H15 H 0.5101 0.2905 1.4653 0.029 Uiso 1 1 calc R . . C16 C 0.45247(9) 0.33247(9) 1.1996(2) 0.0252(2) Uani 1 1 d . . . H16 H 0.4528 0.3908 1.2375 0.030 Uiso 1 1 calc R . . C17 C 0.38073(9) 0.37181(9) 0.8668(2) 0.0251(3) Uani 1 1 d . . . N17 N 0.33713(8) 0.34783(8) 0.7052(2) 0.0271(2) Uani 1 1 d . . . O17 O 0.30727(8) 0.41515(7) 0.58952(19) 0.0327(2) Uani 1 1 d . . . H17 H 0.2721(14) 0.3869(14) 0.470(4) 0.039 Uiso 1 1 d . . . C18 C 0.39274(10) 0.46104(10) 0.9128(3) 0.0310(3) Uani 1 1 d . . . N18 N 0.40229(11) 0.53085(10) 0.9549(3) 0.0443(4) Uani 1 1 d . . . N21 N 0.14341(7) 0.31756(7) -0.12112(17) 0.0207(2) Uani 1 1 d . . . O21 O 0.10997(7) 0.29735(7) -0.29942(17) 0.0278(2) Uani 1 1 d . . . C22 C 0.17219(8) 0.25393(8) 0.0057(2) 0.0209(2) Uani 1 1 d . . . C23 C 0.20953(8) 0.27662(8) 0.1943(2) 0.0215(2) Uani 1 1 d . . . N24 N 0.21743(7) 0.35798(7) 0.25304(18) 0.0229(2) Uani 1 1 d . . . C25 C 0.18619(9) 0.41872(8) 0.1282(2) 0.0223(2) Uani 1 1 d . . . C26 C 0.14874(8) 0.40059(8) -0.0624(2) 0.0216(2) Uani 1 1 d . . . C32 C 0.16039(11) 0.16592(8) -0.0715(3) 0.0300(3) Uani 1 1 d . . . H32A H 0.0997 0.1572 -0.1102 0.045 Uiso 1 1 calc R . . H32B H 0.1764 0.1256 0.0383 0.045 Uiso 1 1 calc R . . H32C H 0.1973 0.1568 -0.1934 0.045 Uiso 1 1 calc R . . C33 C 0.24227(9) 0.21041(9) 0.3418(2) 0.0269(3) Uani 1 1 d . . . H33A H 0.2671 0.2380 0.4647 0.040 Uiso 1 1 calc R . . H33B H 0.2868 0.1762 0.2728 0.040 Uiso 1 1 calc R . . H33C H 0.1943 0.1736 0.3845 0.040 Uiso 1 1 calc R . . C35 C 0.19215(11) 0.50869(9) 0.2031(3) 0.0308(3) Uani 1 1 d . . . H35A H 0.2178 0.5097 0.3426 0.046 Uiso 1 1 calc R . . H35B H 0.1341 0.5336 0.2083 0.046 Uiso 1 1 calc R . . H35C H 0.2284 0.5416 0.1075 0.046 Uiso 1 1 calc R . . C36 C 0.11377(11) 0.46460(9) -0.2097(2) 0.0294(3) Uani 1 1 d . . . H36A H 0.1409 0.4571 -0.3463 0.044 Uiso 1 1 calc R . . H36B H 0.1263 0.5218 -0.1575 0.044 Uiso 1 1 calc R . . H36C H 0.0510 0.4572 -0.2227 0.044 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 C11 0.0206(5) 0.0258(6) 0.0202(5) 0.0007(5) -0.0002(4) -0.0004(4) C12 0.0234(5) 0.0271(6) 0.0213(5) -0.0014(5) -0.0018(4) -0.0016(4) C13 0.0241(5) 0.0254(6) 0.0233(6) -0.0012(5) -0.0014(5) -0.0026(4) C14 0.0192(5) 0.0270(6) 0.0222(5) 0.0006(5) -0.0009(4) -0.0025(4) O14 0.0333(5) 0.0276(5) 0.0288(5) 0.0035(4) -0.0102(4) -0.0026(4) C15 0.0233(6) 0.0290(6) 0.0211(6) -0.0019(5) -0.0031(5) 0.0000(4) C16 0.0263(6) 0.0262(6) 0.0231(6) -0.0026(5) -0.0026(5) 0.0010(5) C17 0.0239(5) 0.0286(6) 0.0229(6) 0.0005(5) -0.0005(5) 0.0015(4) N17 0.0261(5) 0.0320(6) 0.0232(5) 0.0025(5) -0.0023(4) 0.0031(4) O17 0.0372(6) 0.0345(5) 0.0265(5) 0.0037(4) -0.0095(5) 0.0042(4) C18 0.0343(7) 0.0307(7) 0.0281(7) 0.0038(6) -0.0048(6) 0.0028(5) N18 0.0572(10) 0.0326(7) 0.0432(8) 0.0035(7) -0.0076(7) 0.0013(6) N21 0.0224(5) 0.0212(4) 0.0185(5) -0.0002(4) -0.0002(4) 0.0031(4) O21 0.0356(5) 0.0280(5) 0.0200(4) -0.0040(4) -0.0059(4) 0.0047(4) C22 0.0225(5) 0.0193(5) 0.0210(5) 0.0014(4) 0.0029(5) 0.0035(4) C23 0.0205(5) 0.0241(5) 0.0199(5) 0.0049(4) 0.0019(4) 0.0028(4) N24 0.0229(5) 0.0257(5) 0.0200(5) 0.0035(4) 0.0000(4) -0.0012(4) C25 0.0266(6) 0.0199(5) 0.0203(5) 0.0015(4) 0.0003(5) -0.0019(4) C26 0.0260(5) 0.0191(5) 0.0196(5) 0.0013(4) -0.0007(4) 0.0025(4) C32 0.0388(7) 0.0200(5) 0.0310(7) -0.0012(5) 0.0038(6) 0.0050(5) C33 0.0268(6) 0.0294(6) 0.0246(6) 0.0093(5) 0.0005(5) 0.0049(5) C35 0.0438(8) 0.0212(5) 0.0273(6) -0.0006(5) -0.0040(6) -0.0045(5) C36 0.0394(8) 0.0227(6) 0.0261(6) 0.0038(5) -0.0053(6) 0.0060(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 C11 C16 1.3928(19) . ? C11 C12 1.3999(19) . ? C11 C17 1.4670(19) . ? C12 C13 1.3772(19) . ? C12 H12 0.9500 . ? C13 C14 1.4006(19) . ? C13 H13 0.9500 . ? C14 O14 1.3558(17) . ? C14 C15 1.3912(19) . ? O14 H14 0.96(2) . ? C15 C16 1.3842(19) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 N17 1.2939(18) . ? C17 C18 1.448(2) . ? N17 O17 1.3743(16) . ? O17 H17 1.04(2) . ? C18 N18 1.142(2) . ? N21 O21 1.2964(15) . ? N21 C26 1.3632(16) . ? N21 C22 1.3657(16) . ? C22 C23 1.3893(19) . ? C22 C32 1.4829(19) . ? C23 N24 1.3410(17) . ? C23 C33 1.4970(18) . ? N24 C25 1.3383(17) . ? C25 C26 1.3840(19) . ? C25 C35 1.4991(18) . ? C26 C36 1.4847(19) . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16 C11 C12 118.74(13) . . ? C16 C11 C17 120.83(12) . . ? C12 C11 C17 120.43(12) . . ? C13 C12 C11 120.42(13) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C12 C13 C14 120.32(13) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? O14 C14 C15 122.99(12) . . ? O14 C14 C13 117.30(12) . . ? C15 C14 C13 119.70(13) . . ? C14 O14 H14 107.6(12) . . ? C16 C15 C14 119.52(13) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? C15 C16 C11 121.29(13) . . ? C15 C16 H16 119.4 . . ? C11 C16 H16 119.4 . . ? N17 C17 C18 120.92(13) . . ? N17 C17 C11 120.17(13) . . ? C18 C17 C11 118.90(13) . . ? C17 N17 O17 112.56(12) . . ? N17 O17 H17 104.1(12) . . ? N18 C18 C17 178.08(19) . . ? O21 N21 C26 120.28(11) . . ? O21 N21 C22 118.47(11) . . ? C26 N21 C22 121.25(12) . . ? N21 C22 C23 117.84(11) . . ? N21 C22 C32 116.50(12) . . ? C23 C22 C32 125.66(12) . . ? N24 C23 C22 121.93(11) . . ? N24 C23 C33 117.17(12) . . ? C22 C23 C33 120.90(12) . . ? C25 N24 C23 118.77(11) . . ? N24 C25 C26 122.25(12) . . ? N24 C25 C35 117.43(12) . . ? C26 C25 C35 120.32(12) . . ? N21 C26 C25 117.91(11) . . ? N21 C26 C36 116.91(12) . . ? C25 C26 C36 125.19(12) . . ? C22 C32 H32A 109.5 . . ? C22 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C22 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C23 C33 H33A 109.5 . . ? C23 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C23 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C25 C35 H35A 109.5 . . ? C25 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C25 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C26 C36 H36A 109.5 . . ? C26 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C26 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 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 C16 C11 C12 C13 0.9(2) . . . . ? C17 C11 C12 C13 -178.78(12) . . . . ? C11 C12 C13 C14 -0.2(2) . . . . ? C12 C13 C14 O14 179.70(12) . . . . ? C12 C13 C14 C15 -0.78(19) . . . . ? O14 C14 C15 C16 -179.49(13) . . . . ? C13 C14 C15 C16 1.01(19) . . . . ? C14 C15 C16 C11 -0.3(2) . . . . ? C12 C11 C16 C15 -0.7(2) . . . . ? C17 C11 C16 C15 179.01(13) . . . . ? C16 C11 C17 N17 -169.39(13) . . . . ? C12 C11 C17 N17 10.3(2) . . . . ? C16 C11 C17 C18 9.7(2) . . . . ? C12 C11 C17 C18 -170.59(13) . . . . ? C18 C17 N17 O17 1.05(18) . . . . ? C11 C17 N17 O17 -179.84(12) . . . . ? N17 C17 C18 N18 150(5) . . . . ? C11 C17 C18 N18 -29(5) . . . . ? O21 N21 C22 C23 178.66(11) . . . . ? C26 N21 C22 C23 -1.88(18) . . . . ? O21 N21 C22 C32 -1.46(17) . . . . ? C26 N21 C22 C32 178.01(12) . . . . ? N21 C22 C23 N24 0.18(18) . . . . ? C32 C22 C23 N24 -179.69(13) . . . . ? N21 C22 C23 C33 179.77(11) . . . . ? C32 C22 C23 C33 -0.1(2) . . . . ? C22 C23 N24 C25 1.84(19) . . . . ? C33 C23 N24 C25 -177.76(12) . . . . ? C23 N24 C25 C26 -2.25(19) . . . . ? C23 N24 C25 C35 177.07(13) . . . . ? O21 N21 C26 C25 -179.04(11) . . . . ? C22 N21 C26 C25 1.51(18) . . . . ? O21 N21 C26 C36 0.80(18) . . . . ? C22 N21 C26 C36 -178.65(12) . . . . ? N24 C25 C26 N21 0.61(19) . . . . ? C35 C25 C26 N21 -178.69(12) . . . . ? N24 C25 C26 C36 -179.22(13) . . . . ? C35 C25 C26 C36 1.5(2) . . . . ? 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 O17 H17 N24 1.04(2) 1.69(2) 2.7223(16) 169.5(19) . O14 H14 O21 0.96(2) 1.70(2) 2.6631(15) 176(2) 3_557 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 33.14 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.401 _refine_diff_density_min -0.204 _refine_diff_density_rms 0.049 _database_code_depnum_ccdc_archive 'CCDC 910341' ####################################################################### # # 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_PhOx:7 #TrackingRef 'combined.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic 'KE14PCY20 4-HO-PhC(CN)=NOH, 1-[3-pyridylmethyl]-5,6-dimethylbenzimidazole' _chemical_name_common ? _chemical_formula_moiety '(C8 H6 N2 O2) (C15 H15 N3)' _chemical_formula_sum 'C23 H21 N5 O2' _chemical_melting_point ? _exptl_crystal_description plate _exptl_crystal_colour colourless _diffrn_ambient_temperature 120(2) _chemical_formula_weight 399.45 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' _symmetry_int_tables_number 14 _chemical_absolute_configuration ? 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 12.9863(9) _cell_length_b 11.4938(7) _cell_length_c 14.1061(9) _cell_angle_alpha 90.00 _cell_angle_beta 105.555(2) _cell_angle_gamma 90.00 _cell_volume 2028.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 8295 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 32.40 _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.308 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9778 _exptl_absorpt_correction_T_max 0.9879 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_radiation_probe ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 22683 _diffrn_reflns_av_R_equivalents 0.0650 _diffrn_reflns_av_sigmaI/netI 0.0591 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 32.57 _reflns_number_total 6808 _reflns_number_gt 5052 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0750P)^2^+0.2000P] 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_number_reflns 6808 _refine_ls_number_parameters 279 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0725 _refine_ls_R_factor_gt 0.0532 _refine_ls_wR_factor_ref 0.1558 _refine_ls_wR_factor_gt 0.1425 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _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 N11 N -0.04232(8) 0.12115(9) 0.41997(7) 0.0238(2) Uani 1 1 d . . . C12 C -0.13522(10) 0.06026(11) 0.39892(9) 0.0265(2) Uani 1 1 d . . . H12 H -0.1953 0.0828 0.4210 0.032 Uiso 1 1 calc R . . N13 N -0.13421(8) -0.03313(9) 0.34498(7) 0.0264(2) Uani 1 1 d . . . C14 C -0.03278(9) -0.03364(10) 0.32930(8) 0.0232(2) Uani 1 1 d . . . C15 C 0.01274(10) -0.11153(10) 0.27632(9) 0.0260(2) Uani 1 1 d . . . H15 H -0.0273 -0.1757 0.2431 0.031 Uiso 1 1 calc R . . C16 C 0.11689(10) -0.09398(11) 0.27289(9) 0.0263(2) Uani 1 1 d . . . C17 C 0.17722(9) 0.00123(10) 0.32366(8) 0.0249(2) Uani 1 1 d . . . C18 C 0.13146(9) 0.08043(10) 0.37479(8) 0.0240(2) Uani 1 1 d . . . H18 H 0.1709 0.1450 0.4077 0.029 Uiso 1 1 calc R . . C19 C 0.02597(9) 0.06209(10) 0.37618(8) 0.0220(2) Uani 1 1 d . . . C20 C 0.16616(12) -0.17459(13) 0.21307(11) 0.0373(3) Uani 1 1 d . . . H20A H 0.1144 -0.2349 0.1829 0.056 Uiso 1 1 calc R . . H20B H 0.2300 -0.2111 0.2560 0.056 Uiso 1 1 calc R . . H20C H 0.1862 -0.1302 0.1614 0.056 Uiso 1 1 calc R . . C21 C 0.29103(10) 0.01755(12) 0.32070(10) 0.0323(3) Uani 1 1 d . . . H21A H 0.3237 0.0804 0.3656 0.048 Uiso 1 1 calc R . . H21B H 0.2927 0.0376 0.2536 0.048 Uiso 1 1 calc R . . H21C H 0.3309 -0.0547 0.3409 0.048 Uiso 1 1 calc R . . N31 N 0.09178(8) 0.49636(9) 0.39703(7) 0.0277(2) Uani 1 1 d . . . C32 C 0.08167(9) 0.39541(11) 0.44161(8) 0.0248(2) Uani 1 1 d . . . H32 H 0.1431 0.3637 0.4867 0.030 Uiso 1 1 calc R . . C33 C -0.01358(9) 0.33529(10) 0.42518(8) 0.0215(2) Uani 1 1 d . . . C34 C -0.10332(9) 0.38280(11) 0.35974(8) 0.0254(2) Uani 1 1 d . . . H34 H -0.1705 0.3445 0.3472 0.031 Uiso 1 1 calc R . . C35 C -0.09379(10) 0.48650(11) 0.31302(9) 0.0282(3) Uani 1 1 d . . . H35 H -0.1540 0.5204 0.2678 0.034 Uiso 1 1 calc R . . C36 C 0.00497(10) 0.53954(11) 0.33357(9) 0.0275(3) Uani 1 1 d . . . H36 H 0.0115 0.6103 0.3009 0.033 Uiso 1 1 calc R . . C37 C -0.01951(10) 0.22527(10) 0.48153(8) 0.0253(2) Uani 1 1 d . . . H37A H 0.0494 0.2143 0.5319 0.030 Uiso 1 1 calc R . . H37B H -0.0759 0.2344 0.5163 0.030 Uiso 1 1 calc R . . C41 C 0.50310(9) 0.71951(10) 0.43446(8) 0.0222(2) Uani 1 1 d . . . C42 C 0.54730(10) 0.62327(11) 0.39933(9) 0.0262(2) Uani 1 1 d . . . H42 H 0.5147 0.5491 0.3980 0.031 Uiso 1 1 calc R . . C43 C 0.63766(10) 0.63465(10) 0.36658(9) 0.0264(2) Uani 1 1 d . . . H43 H 0.6672 0.5683 0.3434 0.032 Uiso 1 1 calc R . . C44 C 0.68605(9) 0.74351(10) 0.36738(8) 0.0227(2) Uani 1 1 d . . . O44 O 0.77344(7) 0.75104(8) 0.33248(6) 0.0282(2) Uani 1 1 d . . . H44 H 0.7930(13) 0.8269(15) 0.3349(11) 0.034 Uiso 1 1 d . . . C45 C 0.64366(10) 0.83943(10) 0.40382(9) 0.0254(2) Uani 1 1 d . . . H45 H 0.6767 0.9135 0.4057 0.030 Uiso 1 1 calc R . . C46 C 0.55357(10) 0.82707(10) 0.43729(9) 0.0248(2) Uani 1 1 d . . . H46 H 0.5255 0.8929 0.4626 0.030 Uiso 1 1 calc R . . C47 C 0.40589(9) 0.71007(10) 0.46784(8) 0.0237(2) Uani 1 1 d . . . N47 N 0.33476(9) 0.63053(9) 0.43515(8) 0.0292(2) Uani 1 1 d . . . O47 O 0.25141(8) 0.63869(9) 0.47802(7) 0.0341(2) Uani 1 1 d . . . H47 H 0.2031(14) 0.5775(15) 0.4416(11) 0.041 Uiso 1 1 d . . . C48 C 0.39068(10) 0.79494(11) 0.53931(9) 0.0265(2) Uani 1 1 d . . . N48 N 0.38268(10) 0.86213(10) 0.59644(9) 0.0373(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 N11 0.0229(4) 0.0203(5) 0.0298(5) 0.0023(4) 0.0097(4) -0.0021(4) C12 0.0228(5) 0.0235(6) 0.0344(6) 0.0052(5) 0.0096(4) -0.0024(4) N13 0.0223(5) 0.0223(5) 0.0349(5) 0.0047(4) 0.0079(4) -0.0034(4) C14 0.0222(5) 0.0194(5) 0.0273(5) 0.0057(4) 0.0054(4) -0.0026(4) C15 0.0281(6) 0.0187(5) 0.0296(6) 0.0028(4) 0.0048(4) -0.0017(4) C16 0.0270(6) 0.0218(6) 0.0299(6) 0.0037(4) 0.0074(4) 0.0028(4) C17 0.0230(5) 0.0234(6) 0.0283(5) 0.0056(4) 0.0071(4) 0.0012(4) C18 0.0221(5) 0.0215(5) 0.0283(5) 0.0020(4) 0.0066(4) -0.0031(4) C19 0.0220(5) 0.0190(5) 0.0250(5) 0.0038(4) 0.0064(4) -0.0006(4) C20 0.0368(7) 0.0319(7) 0.0443(7) -0.0064(6) 0.0127(6) 0.0045(6) C21 0.0247(6) 0.0343(7) 0.0394(7) 0.0018(5) 0.0114(5) 0.0014(5) N31 0.0261(5) 0.0252(5) 0.0323(5) 0.0004(4) 0.0084(4) -0.0054(4) C32 0.0214(5) 0.0253(6) 0.0268(5) -0.0012(4) 0.0048(4) -0.0013(4) C33 0.0234(5) 0.0200(5) 0.0223(5) -0.0020(4) 0.0082(4) -0.0006(4) C34 0.0220(5) 0.0274(6) 0.0265(5) -0.0014(4) 0.0057(4) -0.0035(4) C35 0.0292(6) 0.0284(6) 0.0255(5) 0.0021(5) 0.0046(4) 0.0031(5) C36 0.0345(6) 0.0208(6) 0.0278(5) 0.0019(4) 0.0095(5) -0.0016(5) C37 0.0286(6) 0.0228(6) 0.0255(5) 0.0014(4) 0.0089(4) -0.0021(4) C41 0.0218(5) 0.0203(5) 0.0237(5) -0.0014(4) 0.0048(4) -0.0037(4) C42 0.0271(6) 0.0200(5) 0.0325(6) -0.0051(4) 0.0099(5) -0.0066(4) C43 0.0261(6) 0.0203(6) 0.0339(6) -0.0071(4) 0.0099(5) -0.0040(4) C44 0.0195(5) 0.0230(5) 0.0245(5) 0.0006(4) 0.0038(4) -0.0022(4) O44 0.0224(4) 0.0258(5) 0.0383(5) 0.0007(4) 0.0115(3) -0.0032(3) C45 0.0242(5) 0.0177(5) 0.0340(6) 0.0009(4) 0.0073(4) -0.0033(4) C46 0.0243(5) 0.0179(5) 0.0322(6) -0.0019(4) 0.0078(4) -0.0012(4) C47 0.0231(5) 0.0200(5) 0.0283(5) -0.0016(4) 0.0073(4) -0.0021(4) N47 0.0254(5) 0.0292(6) 0.0350(5) -0.0023(4) 0.0116(4) -0.0067(4) O47 0.0280(5) 0.0339(5) 0.0448(5) -0.0092(4) 0.0174(4) -0.0115(4) C48 0.0227(5) 0.0244(6) 0.0332(6) -0.0014(5) 0.0090(4) -0.0022(4) N48 0.0345(6) 0.0334(6) 0.0468(6) -0.0099(5) 0.0156(5) -0.0025(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 N11 C12 1.3569(15) . ? N11 C19 1.3867(15) . ? N11 C37 1.4615(15) . ? C12 N13 1.3179(16) . ? C12 H12 0.9500 . ? N13 C14 1.3929(15) . ? C14 C15 1.3951(17) . ? C14 C19 1.3999(16) . ? C15 C16 1.3812(18) . ? C15 H15 0.9500 . ? C16 C17 1.4224(17) . ? C16 C20 1.5064(18) . ? C17 C18 1.3900(17) . ? C17 C21 1.5014(17) . ? C18 C19 1.3913(16) . ? C18 H18 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? N31 C36 1.3333(16) . ? N31 C32 1.3428(16) . ? C32 C33 1.3811(16) . ? C32 H32 0.9500 . ? C33 C34 1.3897(16) . ? C33 C37 1.5066(16) . ? C34 C35 1.3835(17) . ? C34 H34 0.9500 . ? C35 C36 1.3788(18) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? C41 C46 1.3948(16) . ? C41 C42 1.3968(17) . ? C41 C47 1.4649(16) . ? C42 C43 1.3778(17) . ? C42 H42 0.9500 . ? C43 C44 1.3988(16) . ? C43 H43 0.9500 . ? C44 O44 1.3557(14) . ? C44 C45 1.3908(17) . ? O44 H44 0.907(17) . ? C45 C46 1.3815(17) . ? C45 H45 0.9500 . ? C46 H46 0.9500 . ? C47 N47 1.2934(15) . ? C47 C48 1.4538(17) . ? N47 O47 1.3774(14) . ? O47 H47 0.990(18) . ? C48 N48 1.1408(16) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 N11 C19 106.70(10) . . ? C12 N11 C37 125.38(10) . . ? C19 N11 C37 127.85(10) . . ? N13 C12 N11 113.61(11) . . ? N13 C12 H12 123.2 . . ? N11 C12 H12 123.2 . . ? C12 N13 C14 104.56(10) . . ? N13 C14 C15 129.97(11) . . ? N13 C14 C19 109.91(10) . . ? C15 C14 C19 120.13(11) . . ? C16 C15 C14 118.99(11) . . ? C16 C15 H15 120.5 . . ? C14 C15 H15 120.5 . . ? C15 C16 C17 120.47(11) . . ? C15 C16 C20 119.79(12) . . ? C17 C16 C20 119.73(12) . . ? C18 C17 C16 120.71(11) . . ? C18 C17 C21 119.58(11) . . ? C16 C17 C21 119.70(11) . . ? C17 C18 C19 117.88(11) . . ? C17 C18 H18 121.1 . . ? C19 C18 H18 121.1 . . ? N11 C19 C18 132.99(11) . . ? N11 C19 C14 105.22(10) . . ? C18 C19 C14 121.76(11) . . ? C16 C20 H20A 109.5 . . ? C16 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C16 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C17 C21 H21A 109.5 . . ? C17 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C17 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C36 N31 C32 117.69(10) . . ? N31 C32 C33 123.33(11) . . ? N31 C32 H32 118.3 . . ? C33 C32 H32 118.3 . . ? C32 C33 C34 117.95(11) . . ? C32 C33 C37 120.10(10) . . ? C34 C33 C37 121.86(10) . . ? C35 C34 C33 119.26(11) . . ? C35 C34 H34 120.4 . . ? C33 C34 H34 120.4 . . ? C36 C35 C34 118.54(11) . . ? C36 C35 H35 120.7 . . ? C34 C35 H35 120.7 . . ? N31 C36 C35 123.23(11) . . ? N31 C36 H36 118.4 . . ? C35 C36 H36 118.4 . . ? N11 C37 C33 113.87(9) . . ? N11 C37 H37A 108.8 . . ? C33 C37 H37A 108.8 . . ? N11 C37 H37B 108.8 . . ? C33 C37 H37B 108.8 . . ? H37A C37 H37B 107.7 . . ? C46 C41 C42 118.51(11) . . ? C46 C41 C47 119.69(10) . . ? C42 C41 C47 121.80(10) . . ? C43 C42 C41 120.78(11) . . ? C43 C42 H42 119.6 . . ? C41 C42 H42 119.6 . . ? C42 C43 C44 120.22(11) . . ? C42 C43 H43 119.9 . . ? C44 C43 H43 119.9 . . ? O44 C44 C45 122.44(10) . . ? O44 C44 C43 118.17(11) . . ? C45 C44 C43 119.38(11) . . ? C44 O44 H44 107.6(10) . . ? C46 C45 C44 120.01(11) . . ? C46 C45 H45 120.0 . . ? C44 C45 H45 120.0 . . ? C45 C46 C41 121.06(11) . . ? C45 C46 H46 119.5 . . ? C41 C46 H46 119.5 . . ? N47 C47 C48 120.31(11) . . ? N47 C47 C41 122.16(10) . . ? C48 C47 C41 117.53(10) . . ? C47 N47 O47 111.44(10) . . ? N47 O47 H47 100.8(10) . . ? N48 C48 C47 177.50(13) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C19 N11 C12 N13 -0.25(13) . . . . ? C37 N11 C12 N13 -177.38(10) . . . . ? N11 C12 N13 C14 -0.04(13) . . . . ? C12 N13 C14 C15 -179.30(12) . . . . ? C12 N13 C14 C19 0.31(12) . . . . ? N13 C14 C15 C16 -179.00(11) . . . . ? C19 C14 C15 C16 1.43(16) . . . . ? C14 C15 C16 C17 0.80(17) . . . . ? C14 C15 C16 C20 -177.79(11) . . . . ? C15 C16 C17 C18 -2.18(17) . . . . ? C20 C16 C17 C18 176.40(11) . . . . ? C15 C16 C17 C21 178.80(11) . . . . ? C20 C16 C17 C21 -2.61(17) . . . . ? C16 C17 C18 C19 1.25(16) . . . . ? C21 C17 C18 C19 -179.73(10) . . . . ? C12 N11 C19 C18 -177.74(12) . . . . ? C37 N11 C19 C18 -0.7(2) . . . . ? C12 N11 C19 C14 0.42(12) . . . . ? C37 N11 C19 C14 177.46(10) . . . . ? C17 C18 C19 N11 178.91(11) . . . . ? C17 C18 C19 C14 1.01(16) . . . . ? N13 C14 C19 N11 -0.46(12) . . . . ? C15 C14 C19 N11 179.20(10) . . . . ? N13 C14 C19 C18 177.95(10) . . . . ? C15 C14 C19 C18 -2.39(16) . . . . ? C36 N31 C32 C33 -0.29(18) . . . . ? N31 C32 C33 C34 -0.58(18) . . . . ? N31 C32 C33 C37 -177.24(11) . . . . ? C32 C33 C34 C35 0.85(17) . . . . ? C37 C33 C34 C35 177.45(11) . . . . ? C33 C34 C35 C36 -0.29(18) . . . . ? C32 N31 C36 C35 0.90(18) . . . . ? C34 C35 C36 N31 -0.62(19) . . . . ? C12 N11 C37 C33 -109.70(13) . . . . ? C19 N11 C37 C33 73.78(14) . . . . ? C32 C33 C37 N11 -115.14(12) . . . . ? C34 C33 C37 N11 68.33(14) . . . . ? C46 C41 C42 C43 -1.12(17) . . . . ? C47 C41 C42 C43 178.76(11) . . . . ? C41 C42 C43 C44 -0.51(18) . . . . ? C42 C43 C44 O44 -178.59(11) . . . . ? C42 C43 C44 C45 1.60(18) . . . . ? O44 C44 C45 C46 179.15(10) . . . . ? C43 C44 C45 C46 -1.05(17) . . . . ? C44 C45 C46 C41 -0.60(17) . . . . ? C42 C41 C46 C45 1.68(17) . . . . ? C47 C41 C46 C45 -178.21(10) . . . . ? C46 C41 C47 N47 153.50(12) . . . . ? C42 C41 C47 N47 -26.38(17) . . . . ? C46 C41 C47 C48 -25.85(15) . . . . ? C42 C41 C47 C48 154.27(11) . . . . ? C48 C47 N47 O47 -1.26(16) . . . . ? C41 C47 N47 O47 179.41(10) . . . . ? 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 O47 H47 N31 0.990(18) 1.693(18) 2.6474(14) 160.7(15) . O44 H44 N13 0.907(17) 1.852(17) 2.7405(14) 166.1(15) 1_665 _diffrn_measured_fraction_theta_max 0.921 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 0.450 _refine_diff_density_min -0.318 _refine_diff_density_rms 0.058 _database_code_depnum_ccdc_archive 'CCDC 910342' ####################################################################### # # 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_PhOx:6 #TrackingRef 'combined.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic 'KEPCY17 4-HO-PhC(CN)=NOH, [1-(4-pyridylmethyl)-5,6-dimethylbenzimidazole]2' _chemical_name_common ? _chemical_formula_moiety '(C8 H6 N2 O2) (C15 H15 N3)2' _chemical_formula_sum 'C38 H36 N8 O2' _chemical_melting_point ? _exptl_crystal_description prism _exptl_crystal_colour colourless _diffrn_ambient_temperature 120(2) _chemical_formula_weight 636.75 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.1780(3) _cell_length_b 16.1233(9) _cell_length_c 16.2481(9) _cell_angle_alpha 85.088(2) _cell_angle_beta 87.986(3) _cell_angle_gamma 81.153(2) _cell_volume 1592.94(15) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9380 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 33.64 _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9764 _exptl_absorpt_correction_T_max 0.9831 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_radiation_probe ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 37234 _diffrn_reflns_av_R_equivalents 0.0718 _diffrn_reflns_av_sigmaI/netI 0.0756 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.26 _diffrn_reflns_theta_max 33.14 _reflns_number_total 11789 _reflns_number_gt 8616 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0850P)^2^+0.0500P] 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_number_reflns 11789 _refine_ls_number_parameters 443 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0784 _refine_ls_R_factor_gt 0.0569 _refine_ls_wR_factor_ref 0.1714 _refine_ls_wR_factor_gt 0.1541 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _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 N11 N -0.52704(14) 0.17753(6) 0.79069(6) 0.01953(18) Uani 1 1 d . . . C12 C -0.35678(17) 0.11429(7) 0.78250(7) 0.0212(2) Uani 1 1 d . . . H12 H -0.3576 0.0585 0.8066 0.025 Uiso 1 1 calc R . . N13 N -0.19056(15) 0.13743(6) 0.73808(6) 0.02109(18) Uani 1 1 d . . . C14 C -0.25731(17) 0.22263(6) 0.71458(6) 0.01865(19) Uani 1 1 d . . . C15 C -0.14962(17) 0.28010(7) 0.66582(6) 0.0201(2) Uani 1 1 d . . . H15 H -0.0048 0.2638 0.6453 0.024 Uiso 1 1 calc R . . C16 C -0.25782(18) 0.36108(7) 0.64799(6) 0.0204(2) Uani 1 1 d . . . C17 C -0.47595(18) 0.38543(6) 0.67806(6) 0.0203(2) Uani 1 1 d . . . C18 C -0.58176(18) 0.32892(7) 0.72768(7) 0.0205(2) Uani 1 1 d . . . H18 H -0.7263 0.3448 0.7487 0.025 Uiso 1 1 calc R . . C19 C -0.46850(17) 0.24807(7) 0.74560(6) 0.01852(19) Uani 1 1 d . . . C20 C -0.1463(2) 0.42320(7) 0.59371(7) 0.0270(2) Uani 1 1 d . . . H20A H 0.0045 0.3979 0.5811 0.040 Uiso 1 1 calc R . . H20B H -0.1448 0.4741 0.6225 0.040 Uiso 1 1 calc R . . H20C H -0.2262 0.4380 0.5422 0.040 Uiso 1 1 calc R . . C21 C -0.5937(2) 0.47221(7) 0.65459(8) 0.0260(2) Uani 1 1 d . . . H21A H -0.7404 0.4788 0.6804 0.039 Uiso 1 1 calc R . . H21B H -0.6063 0.4805 0.5944 0.039 Uiso 1 1 calc R . . H21C H -0.5114 0.5140 0.6736 0.039 Uiso 1 1 calc R . . N31 N -0.93171(17) 0.28855(7) 1.05178(6) 0.0278(2) Uani 1 1 d . . . C32 C -1.0626(2) 0.24577(8) 1.01373(7) 0.0268(2) Uani 1 1 d . . . H32 H -1.2034 0.2416 1.0377 0.032 Uiso 1 1 calc R . . C33 C -1.00521(18) 0.20729(7) 0.94160(7) 0.0236(2) Uani 1 1 d . . . H33 H -1.1047 0.1776 0.9173 0.028 Uiso 1 1 calc R . . C34 C -0.79974(17) 0.21253(6) 0.90496(6) 0.0195(2) Uani 1 1 d . . . C35 C -0.66355(18) 0.25740(7) 0.94307(7) 0.0228(2) Uani 1 1 d . . . H35 H -0.5227 0.2633 0.9200 0.027 Uiso 1 1 calc R . . C36 C -0.7361(2) 0.29384(7) 1.01581(7) 0.0261(2) Uani 1 1 d . . . H36 H -0.6406 0.3243 1.0413 0.031 Uiso 1 1 calc R . . C37 C -0.74092(18) 0.16907(7) 0.82673(7) 0.0226(2) Uani 1 1 d . . . H37A H -0.7489 0.1084 0.8387 0.027 Uiso 1 1 calc R . . H37B H -0.8528 0.1917 0.7851 0.027 Uiso 1 1 calc R . . N41 N 1.52897(15) 0.24655(6) 0.26678(6) 0.02141(19) Uani 1 1 d . . . C42 C 1.33949(19) 0.23702(7) 0.30874(7) 0.0233(2) Uani 1 1 d . . . H42 H 1.3201 0.1876 0.3426 0.028 Uiso 1 1 calc R . . N43 N 1.18507(16) 0.30269(6) 0.29805(6) 0.02309(19) Uani 1 1 d . . . C44 C 1.28078(17) 0.36016(7) 0.24496(7) 0.0199(2) Uani 1 1 d . . . C45 C 1.19526(18) 0.44104(7) 0.21297(7) 0.0220(2) Uani 1 1 d . . . H45 H 1.0484 0.4645 0.2255 0.026 Uiso 1 1 calc R . . C46 C 1.32867(18) 0.48693(7) 0.16227(7) 0.0220(2) Uani 1 1 d . . . C47 C 1.54785(18) 0.45131(7) 0.14336(7) 0.0217(2) Uani 1 1 d . . . C48 C 1.63342(18) 0.37033(7) 0.17415(7) 0.0211(2) Uani 1 1 d . . . H48 H 1.7794 0.3461 0.1611 0.025 Uiso 1 1 calc R . . C49 C 1.49643(17) 0.32589(6) 0.22504(6) 0.0190(2) Uani 1 1 d . . . C50 C 1.2397(2) 0.57529(7) 0.12927(8) 0.0282(2) Uani 1 1 d . . . H50A H 1.0870 0.5894 0.1479 0.042 Uiso 1 1 calc R . . H50B H 1.2474 0.5792 0.0687 0.042 Uiso 1 1 calc R . . H50C H 1.3271 0.6148 0.1497 0.042 Uiso 1 1 calc R . . C51 C 1.6944(2) 0.50292(8) 0.09169(7) 0.0283(2) Uani 1 1 d . . . H51A H 1.8355 0.4680 0.0813 0.042 Uiso 1 1 calc R . . H51B H 1.7181 0.5512 0.1212 0.042 Uiso 1 1 calc R . . H51C H 1.6248 0.5231 0.0389 0.042 Uiso 1 1 calc R . . N61 N 1.73488(18) 0.03176(6) 0.05426(6) 0.0284(2) Uani 1 1 d . . . C62 C 1.9133(2) 0.03379(7) 0.09820(7) 0.0273(2) Uani 1 1 d . . . H62 H 2.0471 0.0012 0.0822 0.033 Uiso 1 1 calc R . . C63 C 1.91338(19) 0.08078(7) 0.16571(7) 0.0238(2) Uani 1 1 d . . . H63 H 2.0436 0.0791 0.1956 0.029 Uiso 1 1 calc R . . C64 C 1.72054(18) 0.13040(6) 0.18909(6) 0.0199(2) Uani 1 1 d . . . C65 C 1.53448(19) 0.12897(7) 0.14425(7) 0.0229(2) Uani 1 1 d . . . H65 H 1.3991 0.1617 0.1584 0.027 Uiso 1 1 calc R . . C66 C 1.5492(2) 0.07882(7) 0.07811(7) 0.0252(2) Uani 1 1 d . . . H66 H 1.4203 0.0779 0.0482 0.030 Uiso 1 1 calc R . . C67 C 1.72012(19) 0.18246(7) 0.26226(7) 0.0237(2) Uani 1 1 d . . . H67A H 1.7267 0.1446 0.3137 0.028 Uiso 1 1 calc R . . H67B H 1.8532 0.2099 0.2589 0.028 Uiso 1 1 calc R . . C71 C 0.55157(17) 0.16624(7) 0.53870(6) 0.0195(2) Uani 1 1 d . . . C72 C 0.43429(18) 0.24701(7) 0.51984(7) 0.0216(2) Uani 1 1 d . . . H72 H 0.2886 0.2606 0.5406 0.026 Uiso 1 1 calc R . . C73 C 0.52922(19) 0.30683(7) 0.47125(7) 0.0225(2) Uani 1 1 d . . . H73 H 0.4486 0.3613 0.4591 0.027 Uiso 1 1 calc R . . C74 C 0.74334(18) 0.28768(7) 0.43985(7) 0.0216(2) Uani 1 1 d . . . O74 O 0.82530(15) 0.34871(5) 0.39231(6) 0.02898(19) Uani 1 1 d . . . H74 H 0.960(3) 0.3266(10) 0.3659(10) 0.035 Uiso 1 1 d . . . C75 C 0.86110(18) 0.20771(7) 0.45877(7) 0.0217(2) Uani 1 1 d . . . H75 H 1.0072 0.1943 0.4383 0.026 Uiso 1 1 calc R . . C76 C 0.76505(18) 0.14774(7) 0.50740(7) 0.0210(2) Uani 1 1 d . . . H76 H 0.8459 0.0932 0.5196 0.025 Uiso 1 1 calc R . . C77 C 0.45198(18) 0.10327(7) 0.59150(7) 0.0211(2) Uani 1 1 d . . . N77 N 0.26132(16) 0.12193(6) 0.62650(6) 0.02335(19) Uani 1 1 d . . . O77 O 0.19469(14) 0.05447(5) 0.67373(5) 0.02719(19) Uani 1 1 d . . . H77 H 0.065(3) 0.0807(10) 0.6956(10) 0.033 Uiso 1 1 d . . . C78 C 0.5749(2) 0.01930(7) 0.60449(8) 0.0303(3) Uani 1 1 d . . . N78 N 0.6780(2) -0.04556(7) 0.61388(10) 0.0502(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 N11 0.0160(4) 0.0214(4) 0.0212(4) -0.0010(3) 0.0032(3) -0.0045(3) C12 0.0183(5) 0.0208(5) 0.0241(5) -0.0003(4) 0.0007(4) -0.0030(4) N13 0.0171(4) 0.0212(4) 0.0243(4) -0.0004(3) 0.0015(3) -0.0020(3) C14 0.0167(4) 0.0204(5) 0.0188(4) -0.0017(4) 0.0005(4) -0.0029(4) C15 0.0168(4) 0.0233(5) 0.0202(5) -0.0016(4) 0.0025(4) -0.0038(4) C16 0.0210(5) 0.0226(5) 0.0182(5) -0.0009(4) -0.0001(4) -0.0057(4) C17 0.0208(5) 0.0210(5) 0.0194(5) -0.0024(4) -0.0018(4) -0.0035(4) C18 0.0175(5) 0.0231(5) 0.0207(5) -0.0033(4) 0.0003(4) -0.0017(4) C19 0.0168(4) 0.0212(5) 0.0181(4) -0.0011(3) 0.0005(4) -0.0049(4) C20 0.0289(6) 0.0261(5) 0.0262(5) 0.0018(4) 0.0025(5) -0.0080(4) C21 0.0258(5) 0.0221(5) 0.0289(6) -0.0004(4) -0.0032(4) -0.0004(4) N31 0.0272(5) 0.0333(5) 0.0224(5) -0.0021(4) 0.0027(4) -0.0041(4) C32 0.0220(5) 0.0328(6) 0.0249(5) 0.0003(4) 0.0060(4) -0.0043(4) C33 0.0193(5) 0.0273(5) 0.0250(5) -0.0008(4) 0.0025(4) -0.0067(4) C34 0.0173(4) 0.0202(5) 0.0202(5) 0.0023(4) 0.0008(4) -0.0022(4) C35 0.0196(5) 0.0260(5) 0.0229(5) 0.0004(4) 0.0016(4) -0.0058(4) C36 0.0259(6) 0.0300(6) 0.0231(5) -0.0012(4) -0.0012(4) -0.0067(4) C37 0.0173(5) 0.0275(5) 0.0244(5) -0.0043(4) 0.0045(4) -0.0078(4) N41 0.0220(4) 0.0201(4) 0.0219(4) -0.0041(3) 0.0036(3) -0.0021(3) C42 0.0258(5) 0.0210(5) 0.0230(5) -0.0024(4) 0.0050(4) -0.0042(4) N43 0.0231(5) 0.0221(4) 0.0241(4) -0.0016(3) 0.0063(4) -0.0048(3) C44 0.0191(5) 0.0219(5) 0.0196(5) -0.0033(4) 0.0025(4) -0.0054(4) C45 0.0186(5) 0.0231(5) 0.0242(5) -0.0038(4) 0.0000(4) -0.0024(4) C46 0.0228(5) 0.0222(5) 0.0218(5) -0.0015(4) -0.0035(4) -0.0056(4) C47 0.0219(5) 0.0265(5) 0.0187(5) -0.0030(4) -0.0002(4) -0.0090(4) C48 0.0186(5) 0.0269(5) 0.0192(5) -0.0048(4) 0.0021(4) -0.0063(4) C49 0.0195(5) 0.0202(5) 0.0178(4) -0.0044(4) 0.0014(4) -0.0031(4) C50 0.0300(6) 0.0248(5) 0.0299(6) 0.0012(4) -0.0053(5) -0.0056(4) C51 0.0296(6) 0.0323(6) 0.0250(5) 0.0027(4) -0.0006(5) -0.0141(5) N61 0.0334(6) 0.0269(5) 0.0254(5) -0.0078(4) 0.0039(4) -0.0040(4) C62 0.0278(6) 0.0254(5) 0.0276(6) -0.0049(4) 0.0046(5) -0.0004(4) C63 0.0214(5) 0.0247(5) 0.0247(5) -0.0030(4) 0.0007(4) -0.0015(4) C64 0.0218(5) 0.0175(4) 0.0199(5) -0.0010(3) 0.0024(4) -0.0026(4) C65 0.0226(5) 0.0221(5) 0.0238(5) -0.0035(4) 0.0021(4) -0.0025(4) C66 0.0263(5) 0.0267(5) 0.0238(5) -0.0035(4) -0.0018(4) -0.0061(4) C67 0.0236(5) 0.0221(5) 0.0246(5) -0.0057(4) -0.0015(4) 0.0013(4) C71 0.0192(5) 0.0208(5) 0.0188(5) -0.0022(4) 0.0019(4) -0.0037(4) C72 0.0189(5) 0.0234(5) 0.0215(5) -0.0024(4) 0.0027(4) -0.0004(4) C73 0.0227(5) 0.0210(5) 0.0223(5) -0.0006(4) 0.0033(4) 0.0001(4) C74 0.0222(5) 0.0229(5) 0.0191(5) -0.0015(4) 0.0040(4) -0.0030(4) O74 0.0286(4) 0.0227(4) 0.0330(5) 0.0031(3) 0.0132(4) -0.0016(3) C75 0.0186(5) 0.0241(5) 0.0218(5) -0.0020(4) 0.0039(4) -0.0020(4) C76 0.0190(5) 0.0207(5) 0.0223(5) -0.0015(4) 0.0026(4) -0.0009(4) C77 0.0208(5) 0.0203(5) 0.0220(5) -0.0028(4) 0.0025(4) -0.0033(4) N77 0.0222(4) 0.0229(4) 0.0248(5) -0.0001(3) 0.0038(4) -0.0051(3) O77 0.0246(4) 0.0227(4) 0.0329(4) 0.0013(3) 0.0107(3) -0.0039(3) C78 0.0287(6) 0.0228(5) 0.0387(7) -0.0012(5) 0.0129(5) -0.0052(4) N78 0.0429(7) 0.0252(6) 0.0775(10) 0.0050(6) 0.0242(7) -0.0003(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 N11 C12 1.3592(14) . ? N11 C19 1.3878(13) . ? N11 C37 1.4474(13) . ? C12 N13 1.3170(14) . ? C12 H12 0.9500 . ? N13 C14 1.3965(14) . ? C14 C19 1.3961(14) . ? C14 C15 1.3985(14) . ? C15 C16 1.3841(15) . ? C15 H15 0.9500 . ? C16 C17 1.4257(15) . ? C16 C20 1.5079(15) . ? C17 C18 1.3884(15) . ? C17 C21 1.4993(15) . ? C18 C19 1.3938(15) . ? C18 H18 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? N31 C36 1.3352(15) . ? N31 C32 1.3385(16) . ? C32 C33 1.3827(16) . ? C32 H32 0.9500 . ? C33 C34 1.3943(15) . ? C33 H33 0.9500 . ? C34 C35 1.3840(15) . ? C34 C37 1.5101(15) . ? C35 C36 1.3941(16) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? N41 C42 1.3565(14) . ? N41 C49 1.3852(14) . ? N41 C67 1.4489(14) . ? C42 N43 1.3156(15) . ? C42 H42 0.9500 . ? N43 C44 1.3957(13) . ? C44 C45 1.3931(15) . ? C44 C49 1.3997(15) . ? C45 C46 1.3933(15) . ? C45 H45 0.9500 . ? C46 C47 1.4211(16) . ? C46 C50 1.5059(16) . ? C47 C48 1.3889(16) . ? C47 C51 1.5085(15) . ? C48 C49 1.3962(14) . ? C48 H48 0.9500 . ? C50 H50A 0.9800 . ? C50 H50B 0.9800 . ? C50 H50C 0.9800 . ? C51 H51A 0.9800 . ? C51 H51B 0.9800 . ? C51 H51C 0.9800 . ? N61 C66 1.3391(16) . ? N61 C62 1.3401(17) . ? C62 C63 1.3855(16) . ? C62 H62 0.9500 . ? C63 C64 1.3895(15) . ? C63 H63 0.9500 . ? C64 C65 1.3866(16) . ? C64 C67 1.5126(14) . ? C65 C66 1.3916(15) . ? C65 H65 0.9500 . ? C66 H66 0.9500 . ? C67 H67A 0.9900 . ? C67 H67B 0.9900 . ? C71 C76 1.3946(15) . ? C71 C72 1.4042(15) . ? C71 C77 1.4668(15) . ? C72 C73 1.3815(15) . ? C72 H72 0.9500 . ? C73 C74 1.3998(15) . ? C73 H73 0.9500 . ? C74 O74 1.3479(13) . ? C74 C75 1.3948(15) . ? O74 H74 0.957(17) . ? C75 C76 1.3871(15) . ? C75 H75 0.9500 . ? C76 H76 0.9500 . ? C77 N77 1.2941(14) . ? C77 C78 1.4492(16) . ? N77 O77 1.3835(12) . ? O77 H77 0.921(16) . ? C78 N78 1.1390(17) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 N11 C19 106.40(8) . . ? C12 N11 C37 126.32(9) . . ? C19 N11 C37 126.46(9) . . ? N13 C12 N11 113.79(10) . . ? N13 C12 H12 123.1 . . ? N11 C12 H12 123.1 . . ? C12 N13 C14 104.41(9) . . ? C19 C14 N13 109.89(9) . . ? C19 C14 C15 119.82(10) . . ? N13 C14 C15 130.25(9) . . ? C16 C15 C14 118.82(10) . . ? C16 C15 H15 120.6 . . ? C14 C15 H15 120.6 . . ? C15 C16 C17 120.72(10) . . ? C15 C16 C20 119.52(10) . . ? C17 C16 C20 119.73(10) . . ? C18 C17 C16 120.55(10) . . ? C18 C17 C21 119.68(10) . . ? C16 C17 C21 119.76(10) . . ? C17 C18 C19 117.66(10) . . ? C17 C18 H18 121.2 . . ? C19 C18 H18 121.2 . . ? N11 C19 C18 132.11(9) . . ? N11 C19 C14 105.47(9) . . ? C18 C19 C14 122.38(10) . . ? C16 C20 H20A 109.5 . . ? C16 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C16 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C17 C21 H21A 109.5 . . ? C17 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C17 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C36 N31 C32 116.35(10) . . ? N31 C32 C33 123.93(11) . . ? N31 C32 H32 118.0 . . ? C33 C32 H32 118.0 . . ? C32 C33 C34 119.26(10) . . ? C32 C33 H33 120.4 . . ? C34 C33 H33 120.4 . . ? C35 C34 C33 117.48(10) . . ? C35 C34 C37 124.51(9) . . ? C33 C34 C37 118.01(9) . . ? C34 C35 C36 119.00(10) . . ? C34 C35 H35 120.5 . . ? C36 C35 H35 120.5 . . ? N31 C36 C35 123.98(11) . . ? N31 C36 H36 118.0 . . ? C35 C36 H36 118.0 . . ? N11 C37 C34 115.70(9) . . ? N11 C37 H37A 108.4 . . ? C34 C37 H37A 108.4 . . ? N11 C37 H37B 108.4 . . ? C34 C37 H37B 108.4 . . ? H37A C37 H37B 107.4 . . ? C42 N41 C49 106.78(9) . . ? C42 N41 C67 125.58(10) . . ? C49 N41 C67 127.47(9) . . ? N43 C42 N41 113.65(10) . . ? N43 C42 H42 123.2 . . ? N41 C42 H42 123.2 . . ? C42 N43 C44 104.53(9) . . ? C45 C44 N43 130.21(10) . . ? C45 C44 C49 119.96(10) . . ? N43 C44 C49 109.83(9) . . ? C44 C45 C46 118.91(10) . . ? C44 C45 H45 120.5 . . ? C46 C45 H45 120.5 . . ? C45 C46 C47 120.28(10) . . ? C45 C46 C50 119.31(10) . . ? C47 C46 C50 120.40(10) . . ? C48 C47 C46 121.16(10) . . ? C48 C47 C51 118.89(10) . . ? C46 C47 C51 119.91(10) . . ? C47 C48 C49 117.35(10) . . ? C47 C48 H48 121.3 . . ? C49 C48 H48 121.3 . . ? N41 C49 C48 132.44(10) . . ? N41 C49 C44 105.21(9) . . ? C48 C49 C44 122.33(10) . . ? C46 C50 H50A 109.5 . . ? C46 C50 H50B 109.5 . . ? H50A C50 H50B 109.5 . . ? C46 C50 H50C 109.5 . . ? H50A C50 H50C 109.5 . . ? H50B C50 H50C 109.5 . . ? C47 C51 H51A 109.5 . . ? C47 C51 H51B 109.5 . . ? H51A C51 H51B 109.5 . . ? C47 C51 H51C 109.5 . . ? H51A C51 H51C 109.5 . . ? H51B C51 H51C 109.5 . . ? C66 N61 C62 116.71(10) . . ? N61 C62 C63 123.65(11) . . ? N61 C62 H62 118.2 . . ? C63 C62 H62 118.2 . . ? C62 C63 C64 119.13(11) . . ? C62 C63 H63 120.4 . . ? C64 C63 H63 120.4 . . ? C65 C64 C63 117.90(10) . . ? C65 C64 C67 122.72(10) . . ? C63 C64 C67 119.38(10) . . ? C64 C65 C66 118.93(10) . . ? C64 C65 H65 120.5 . . ? C66 C65 H65 120.5 . . ? N61 C66 C65 123.66(11) . . ? N61 C66 H66 118.2 . . ? C65 C66 H66 118.2 . . ? N41 C67 C64 113.28(9) . . ? N41 C67 H67A 108.9 . . ? C64 C67 H67A 108.9 . . ? N41 C67 H67B 108.9 . . ? C64 C67 H67B 108.9 . . ? H67A C67 H67B 107.7 . . ? C76 C71 C72 118.72(10) . . ? C76 C71 C77 120.86(10) . . ? C72 C71 C77 120.41(9) . . ? C73 C72 C71 120.46(10) . . ? C73 C72 H72 119.8 . . ? C71 C72 H72 119.8 . . ? C72 C73 C74 120.47(10) . . ? C72 C73 H73 119.8 . . ? C74 C73 H73 119.8 . . ? O74 C74 C75 123.26(10) . . ? O74 C74 C73 117.41(10) . . ? C75 C74 C73 119.33(10) . . ? C74 O74 H74 110.8(9) . . ? C76 C75 C74 120.04(10) . . ? C76 C75 H75 120.0 . . ? C74 C75 H75 120.0 . . ? C75 C76 C71 120.98(10) . . ? C75 C76 H76 119.5 . . ? C71 C76 H76 119.5 . . ? N77 C77 C78 120.63(10) . . ? N77 C77 C71 121.34(10) . . ? C78 C77 C71 118.02(10) . . ? C77 N77 O77 112.97(9) . . ? N77 O77 H77 99.8(10) . . ? N78 C78 C77 177.61(14) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C19 N11 C12 N13 1.61(12) . . . . ? C37 N11 C12 N13 171.71(10) . . . . ? N11 C12 N13 C14 -0.47(12) . . . . ? C12 N13 C14 C19 -0.88(12) . . . . ? C12 N13 C14 C15 -178.94(11) . . . . ? C19 C14 C15 C16 -1.28(15) . . . . ? N13 C14 C15 C16 176.62(10) . . . . ? C14 C15 C16 C17 -0.59(16) . . . . ? C14 C15 C16 C20 -178.45(9) . . . . ? C15 C16 C17 C18 1.74(16) . . . . ? C20 C16 C17 C18 179.59(10) . . . . ? C15 C16 C17 C21 -177.07(10) . . . . ? C20 C16 C17 C21 0.78(15) . . . . ? C16 C17 C18 C19 -0.94(15) . . . . ? C21 C17 C18 C19 177.87(10) . . . . ? C12 N11 C19 C18 175.70(11) . . . . ? C37 N11 C19 C18 5.62(18) . . . . ? C12 N11 C19 C14 -2.01(11) . . . . ? C37 N11 C19 C14 -172.09(9) . . . . ? C17 C18 C19 N11 -178.37(10) . . . . ? C17 C18 C19 C14 -0.98(16) . . . . ? N13 C14 C19 N11 1.82(12) . . . . ? C15 C14 C19 N11 -179.88(9) . . . . ? N13 C14 C19 C18 -176.17(10) . . . . ? C15 C14 C19 C18 2.13(16) . . . . ? C36 N31 C32 C33 0.70(19) . . . . ? N31 C32 C33 C34 -0.12(19) . . . . ? C32 C33 C34 C35 -0.63(17) . . . . ? C32 C33 C34 C37 179.36(11) . . . . ? C33 C34 C35 C36 0.77(17) . . . . ? C37 C34 C35 C36 -179.21(10) . . . . ? C32 N31 C36 C35 -0.54(18) . . . . ? C34 C35 C36 N31 -0.19(19) . . . . ? C12 N11 C37 C34 115.37(12) . . . . ? C19 N11 C37 C34 -76.47(14) . . . . ? C35 C34 C37 N11 -0.86(16) . . . . ? C33 C34 C37 N11 179.15(10) . . . . ? C49 N41 C42 N43 0.32(13) . . . . ? C67 N41 C42 N43 -175.21(10) . . . . ? N41 C42 N43 C44 -0.17(12) . . . . ? C42 N43 C44 C45 -179.27(11) . . . . ? C42 N43 C44 C49 -0.04(12) . . . . ? N43 C44 C45 C46 178.26(10) . . . . ? C49 C44 C45 C46 -0.90(16) . . . . ? C44 C45 C46 C47 0.33(16) . . . . ? C44 C45 C46 C50 -178.34(10) . . . . ? C45 C46 C47 C48 0.50(16) . . . . ? C50 C46 C47 C48 179.15(10) . . . . ? C45 C46 C47 C51 -177.14(10) . . . . ? C50 C46 C47 C51 1.51(16) . . . . ? C46 C47 C48 C49 -0.72(15) . . . . ? C51 C47 C48 C49 176.94(9) . . . . ? C42 N41 C49 C48 178.38(11) . . . . ? C67 N41 C49 C48 -6.20(18) . . . . ? C42 N41 C49 C44 -0.31(11) . . . . ? C67 N41 C49 C44 175.11(10) . . . . ? C47 C48 C49 N41 -178.37(10) . . . . ? C47 C48 C49 C44 0.14(15) . . . . ? C45 C44 C49 N41 179.54(9) . . . . ? N43 C44 C49 N41 0.22(11) . . . . ? C45 C44 C49 C48 0.68(16) . . . . ? N43 C44 C49 C48 -178.64(9) . . . . ? C66 N61 C62 C63 0.43(18) . . . . ? N61 C62 C63 C64 -1.44(18) . . . . ? C62 C63 C64 C65 1.36(16) . . . . ? C62 C63 C64 C67 -179.44(10) . . . . ? C63 C64 C65 C66 -0.39(16) . . . . ? C67 C64 C65 C66 -179.57(10) . . . . ? C62 N61 C66 C65 0.63(18) . . . . ? C64 C65 C66 N61 -0.64(18) . . . . ? C42 N41 C67 C64 91.72(13) . . . . ? C49 N41 C67 C64 -82.89(13) . . . . ? C65 C64 C67 N41 -15.88(15) . . . . ? C63 C64 C67 N41 164.96(10) . . . . ? C76 C71 C72 C73 -0.06(16) . . . . ? C77 C71 C72 C73 178.92(10) . . . . ? C71 C72 C73 C74 0.26(17) . . . . ? C72 C73 C74 O74 179.45(10) . . . . ? C72 C73 C74 C75 -0.62(17) . . . . ? O74 C74 C75 C76 -179.29(10) . . . . ? C73 C74 C75 C76 0.79(16) . . . . ? C74 C75 C76 C71 -0.60(16) . . . . ? C72 C71 C76 C75 0.23(16) . . . . ? C77 C71 C76 C75 -178.74(10) . . . . ? C76 C71 C77 N77 174.11(10) . . . . ? C72 C71 C77 N77 -4.85(16) . . . . ? C76 C71 C77 C78 -5.03(16) . . . . ? C72 C71 C77 C78 176.02(11) . . . . ? C78 C77 N77 O77 -0.96(15) . . . . ? C71 C77 N77 O77 179.93(9) . . . . ? N77 C77 C78 N78 -159(4) . . . . ? C71 C77 C78 N78 20(4) . . . . ? 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 O77 H77 N13 0.921(16) 1.843(17) 2.7627(12) 177.7(15) . O74 H74 N43 0.957(17) 1.759(17) 2.6990(12) 166.6(15) . _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 33.14 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.401 _refine_diff_density_min -0.310 _refine_diff_density_rms 0.064 _database_code_depnum_ccdc_archive 'CCDC 910343' ####################################################################### # # 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_PhOx:4 _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety '(C8 H6 N2 O2) (C15 H13 N3)' _chemical_formula_sum 'C23 H19 N5 O2' _chemical_melting_point ? _exptl_crystal_description ? _exptl_crystal_colour ? _diffrn_ambient_temperature 120(2) _chemical_formula_weight 397.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 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' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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' _symmetry_int_tables_number 14 _chemical_absolute_configuration ? 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 12.1479(8) _cell_length_b 12.4551(9) _cell_length_c 13.6598(10) _cell_angle_alpha 90.00 _cell_angle_beta 105.563(3) _cell_angle_gamma 90.00 _cell_volume 1991.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.326 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.714 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.8361 _exptl_absorpt_correction_T_max 0.9067 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_radiation_probe ? _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 8390 _diffrn_reflns_av_R_equivalents 0.0698 _diffrn_reflns_av_sigmaI/netI 0.1086 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 4.33 _diffrn_reflns_theta_max 69.60 _reflns_number_total 3387 _reflns_number_gt 2856 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _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^ > 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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3387 _refine_ls_number_parameters 277 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0936 _refine_ls_R_factor_gt 0.0394 _refine_ls_wR_factor_ref 0.1405 _refine_ls_wR_factor_gt 0.1298 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _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 N11 N -0.07455(9) 0.20302(10) 0.36430(8) 0.0232(3) Uani 1 1 d . . . C12 C 0.02682(10) 0.14944(12) 0.39256(10) 0.0229(3) Uani 1 1 d . . . N13 N 0.10764(9) 0.21212(11) 0.44931(9) 0.0268(3) Uani 1 1 d . . . C14 C 0.05585(12) 0.30857(13) 0.45766(11) 0.0298(3) Uani 1 1 d . . . H14 H 0.0931 0.3691 0.4943 0.036 Uiso 1 1 calc R . . C15 C -0.05625(12) 0.30448(13) 0.40589(11) 0.0291(3) Uani 1 1 d . . . H15 H -0.1111 0.3603 0.3996 0.035 Uiso 1 1 calc R . . N21 N -0.46516(9) 0.06115(11) 0.28665(9) 0.0278(3) Uani 1 1 d . . . C22 C -0.37117(11) 0.09259(12) 0.26115(10) 0.0251(3) Uani 1 1 d . . . H22 H -0.3713 0.0878 0.1917 0.030 Uiso 1 1 calc R . . C23 C -0.27400(10) 0.13159(12) 0.32945(10) 0.0230(3) Uani 1 1 d . . . C24 C -0.27260(12) 0.13577(13) 0.43155(10) 0.0273(3) Uani 1 1 d . . . H24 H -0.2071 0.1608 0.4813 0.033 Uiso 1 1 calc R . . C25 C -0.36977(12) 0.10231(13) 0.45914(11) 0.0303(3) Uani 1 1 d . . . H25 H -0.3710 0.1037 0.5284 0.036 Uiso 1 1 calc R . . C26 C -0.46316(11) 0.06755(13) 0.38561(11) 0.0288(3) Uani 1 1 d . . . H26 H -0.5295 0.0470 0.4052 0.035 Uiso 1 1 calc R . . C27 C -0.17761(10) 0.17034(12) 0.28763(10) 0.0257(3) Uani 1 1 d . . . H27A H -0.1574 0.1122 0.2462 0.031 Uiso 1 1 calc R . . H27B H -0.2054 0.2320 0.2419 0.031 Uiso 1 1 calc R . . C31 C 0.04509(11) 0.03973(12) 0.36159(9) 0.0247(3) Uani 1 1 d . . . C32 C -0.03140(12) -0.04304(13) 0.36453(10) 0.0287(3) Uani 1 1 d . . . H32 H -0.0968 -0.0290 0.3881 0.034 Uiso 1 1 calc R . . C33 C -0.01239(13) -0.14547(14) 0.33333(11) 0.0352(4) Uani 1 1 d . . . H33 H -0.0648 -0.2014 0.3358 0.042 Uiso 1 1 calc R . . C34 C 0.08264(15) -0.16719(14) 0.29839(11) 0.0376(4) Uani 1 1 d . . . H34 H 0.0949 -0.2374 0.2762 0.045 Uiso 1 1 calc R . . C35 C 0.15968(13) -0.08532(15) 0.29611(11) 0.0352(4) Uani 1 1 d . . . H35 H 0.2248 -0.0997 0.2723 0.042 Uiso 1 1 calc R . . C36 C 0.14207(11) 0.01697(13) 0.32829(10) 0.0292(3) Uani 1 1 d . . . H36 H 0.1960 0.0721 0.3278 0.035 Uiso 1 1 calc R . . C41 C 0.58707(10) 0.34104(11) 0.56768(10) 0.0229(3) Uani 1 1 d . . . C42 C 0.48799(11) 0.34385(13) 0.48714(10) 0.0263(3) Uani 1 1 d . . . H42 H 0.4860 0.3868 0.4292 0.032 Uiso 1 1 calc R . . C43 C 0.39252(11) 0.28469(13) 0.49083(10) 0.0274(3) Uani 1 1 d . . . H43 H 0.3254 0.2876 0.4358 0.033 Uiso 1 1 calc R . . C44 C 0.39477(10) 0.22096(12) 0.57513(10) 0.0248(3) Uani 1 1 d . . . O44 O 0.30412(8) 0.16219(10) 0.58427(8) 0.0305(3) Uani 1 1 d . . . H44 H 0.2342(15) 0.1787(16) 0.5261(14) 0.037 Uiso 1 1 d . . . C45 C 0.49418(11) 0.21624(12) 0.65548(10) 0.0247(3) Uani 1 1 d . . . H45 H 0.4967 0.1718 0.7126 0.030 Uiso 1 1 calc R . . C46 C 0.58873(10) 0.27615(12) 0.65192(10) 0.0241(3) Uani 1 1 d . . . H46 H 0.6556 0.2733 0.7072 0.029 Uiso 1 1 calc R . . C47 C 0.68891(10) 0.40317(12) 0.56396(10) 0.0243(3) Uani 1 1 d . . . N47 N 0.77359(9) 0.41387(11) 0.64379(9) 0.0280(3) Uani 1 1 d . . . O47 O 0.86050(8) 0.47475(10) 0.62522(8) 0.0343(3) Uani 1 1 d . . . H47 H 0.9215(15) 0.4627(18) 0.6853(14) 0.041 Uiso 1 1 d . . . C48 C 0.69527(10) 0.44907(13) 0.46811(11) 0.0285(3) Uani 1 1 d . . . N48 N 0.70449(11) 0.48254(14) 0.39256(10) 0.0409(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 N11 0.0199(5) 0.0239(7) 0.0265(5) -0.0012(4) 0.0074(4) -0.0014(4) C12 0.0200(6) 0.0252(8) 0.0243(6) 0.0012(5) 0.0074(5) -0.0022(5) N13 0.0235(5) 0.0267(8) 0.0293(6) -0.0019(5) 0.0057(4) -0.0051(4) C14 0.0312(7) 0.0270(9) 0.0320(7) -0.0050(6) 0.0098(6) -0.0069(6) C15 0.0312(7) 0.0258(8) 0.0331(7) -0.0011(6) 0.0136(6) 0.0008(5) N21 0.0211(5) 0.0276(8) 0.0330(6) 0.0020(5) 0.0043(5) 0.0009(4) C22 0.0218(6) 0.0272(8) 0.0258(6) 0.0017(5) 0.0053(5) 0.0021(5) C23 0.0208(6) 0.0232(8) 0.0251(6) 0.0014(5) 0.0066(5) 0.0027(5) C24 0.0269(7) 0.0290(9) 0.0266(7) -0.0032(5) 0.0083(5) -0.0022(5) C25 0.0333(7) 0.0305(9) 0.0314(7) -0.0034(6) 0.0163(6) -0.0031(6) C26 0.0247(6) 0.0261(8) 0.0391(8) 0.0008(6) 0.0145(6) 0.0006(5) C27 0.0211(6) 0.0315(9) 0.0237(6) 0.0015(5) 0.0046(5) -0.0013(5) C31 0.0251(6) 0.0267(9) 0.0208(6) 0.0015(5) 0.0036(5) 0.0008(5) C32 0.0285(7) 0.0280(9) 0.0281(6) 0.0014(5) 0.0051(5) -0.0023(5) C33 0.0432(8) 0.0292(10) 0.0295(7) 0.0004(6) 0.0037(6) -0.0048(6) C34 0.0534(9) 0.0267(10) 0.0302(7) -0.0019(6) 0.0067(7) 0.0090(7) C35 0.0382(8) 0.0369(10) 0.0307(7) 0.0040(6) 0.0093(6) 0.0132(6) C36 0.0269(7) 0.0319(9) 0.0290(7) 0.0046(6) 0.0076(6) 0.0049(5) C41 0.0208(6) 0.0226(8) 0.0256(6) -0.0015(5) 0.0069(5) 0.0012(5) C42 0.0244(6) 0.0298(8) 0.0244(6) 0.0015(5) 0.0061(5) 0.0019(5) C43 0.0218(6) 0.0319(9) 0.0261(6) -0.0003(6) 0.0024(5) 0.0009(5) C44 0.0209(6) 0.0249(8) 0.0291(7) -0.0046(5) 0.0079(5) -0.0011(5) O44 0.0226(5) 0.0328(7) 0.0359(6) 0.0000(4) 0.0077(4) -0.0062(4) C45 0.0262(6) 0.0240(8) 0.0246(6) -0.0010(5) 0.0082(5) 0.0012(5) C46 0.0216(6) 0.0252(8) 0.0250(6) -0.0013(5) 0.0055(5) 0.0025(5) C47 0.0207(6) 0.0246(8) 0.0276(6) 0.0019(5) 0.0065(5) 0.0030(5) N47 0.0199(5) 0.0295(8) 0.0350(6) 0.0032(5) 0.0080(5) -0.0008(4) O47 0.0210(5) 0.0412(8) 0.0388(6) 0.0082(5) 0.0048(4) -0.0069(4) C48 0.0197(6) 0.0312(9) 0.0337(7) 0.0055(6) 0.0057(5) 0.0018(5) N48 0.0335(7) 0.0504(10) 0.0394(7) 0.0146(7) 0.0108(6) 0.0015(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 N11 C12 1.3623(17) . ? N11 C15 1.379(2) . ? N11 C27 1.4581(17) . ? C12 N13 1.3288(18) . ? C12 C31 1.465(2) . ? N13 C14 1.3750(19) . ? C14 C15 1.357(2) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? N21 C22 1.3385(17) . ? N21 C26 1.3479(19) . ? C22 C23 1.3816(19) . ? C22 H22 0.9500 . ? C23 C24 1.3911(18) . ? C23 C27 1.5131(16) . ? C24 C25 1.3956(19) . ? C24 H24 0.9500 . ? C25 C26 1.368(2) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C31 C32 1.396(2) . ? C31 C36 1.4010(18) . ? C32 C33 1.384(2) . ? C32 H32 0.9500 . ? C33 C34 1.389(2) . ? C33 H33 0.9500 . ? C34 C35 1.390(2) . ? C34 H34 0.9500 . ? C35 C36 1.383(2) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C41 C42 1.3963(19) . ? C41 C46 1.4020(18) . ? C41 C47 1.4716(17) . ? C42 C43 1.386(2) . ? C42 H42 0.9500 . ? C43 C44 1.393(2) . ? C43 H43 0.9500 . ? C44 O44 1.3558(16) . ? C44 C45 1.398(2) . ? O44 H44 1.016(19) . ? C45 C46 1.3813(19) . ? C45 H45 0.9500 . ? C46 H46 0.9500 . ? C47 N47 1.2897(17) . ? C47 C48 1.4496(18) . ? N47 O47 1.3776(15) . ? O47 H47 0.959(19) . ? C48 N48 1.146(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 C12 N11 C15 107.37(11) . . ? C12 N11 C27 127.12(12) . . ? C15 N11 C27 124.34(12) . . ? N13 C12 N11 110.35(13) . . ? N13 C12 C31 124.82(12) . . ? N11 C12 C31 124.79(12) . . ? C12 N13 C14 106.18(12) . . ? C15 C14 N13 109.97(13) . . ? C15 C14 H14 125.0 . . ? N13 C14 H14 125.0 . . ? C14 C15 N11 106.12(13) . . ? C14 C15 H15 126.9 . . ? N11 C15 H15 126.9 . . ? C22 N21 C26 117.17(12) . . ? N21 C22 C23 124.13(12) . . ? N21 C22 H22 117.9 . . ? C23 C22 H22 117.9 . . ? C22 C23 C24 117.94(12) . . ? C22 C23 C27 117.70(11) . . ? C24 C23 C27 124.33(12) . . ? C23 C24 C25 118.41(13) . . ? C23 C24 H24 120.8 . . ? C25 C24 H24 120.8 . . ? C26 C25 C24 119.41(12) . . ? C26 C25 H25 120.3 . . ? C24 C25 H25 120.3 . . ? N21 C26 C25 122.90(11) . . ? N21 C26 H26 118.5 . . ? C25 C26 H26 118.5 . . ? N11 C27 C23 114.85(11) . . ? N11 C27 H27A 108.6 . . ? C23 C27 H27A 108.6 . . ? N11 C27 H27B 108.6 . . ? C23 C27 H27B 108.6 . . ? H27A C27 H27B 107.5 . . ? C32 C31 C36 118.96(14) . . ? C32 C31 C12 121.81(12) . . ? C36 C31 C12 119.22(13) . . ? C33 C32 C31 120.31(13) . . ? C33 C32 H32 119.8 . . ? C31 C32 H32 119.8 . . ? C32 C33 C34 120.54(15) . . ? C32 C33 H33 119.7 . . ? C34 C33 H33 119.7 . . ? C33 C34 C35 119.43(15) . . ? C33 C34 H34 120.3 . . ? C35 C34 H34 120.3 . . ? C36 C35 C34 120.41(14) . . ? C36 C35 H35 119.8 . . ? C34 C35 H35 119.8 . . ? C35 C36 C31 120.32(14) . . ? C35 C36 H36 119.8 . . ? C31 C36 H36 119.8 . . ? C42 C41 C46 118.73(12) . . ? C42 C41 C47 120.97(12) . . ? C46 C41 C47 120.30(12) . . ? C43 C42 C41 120.72(13) . . ? C43 C42 H42 119.6 . . ? C41 C42 H42 119.6 . . ? C42 C43 C44 120.12(12) . . ? C42 C43 H43 119.9 . . ? C44 C43 H43 119.9 . . ? O44 C44 C43 123.20(12) . . ? O44 C44 C45 117.18(12) . . ? C43 C44 C45 119.62(12) . . ? C44 O44 H44 110.4(10) . . ? C46 C45 C44 120.05(13) . . ? C46 C45 H45 120.0 . . ? C44 C45 H45 120.0 . . ? C45 C46 C41 120.75(12) . . ? C45 C46 H46 119.6 . . ? C41 C46 H46 119.6 . . ? N47 C47 C48 119.95(12) . . ? N47 C47 C41 120.82(12) . . ? C48 C47 C41 119.19(11) . . ? C47 N47 O47 112.21(11) . . ? N47 O47 H47 102.2(12) . . ? N48 C48 C47 176.94(16) . . ? 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 N11 C12 N13 -0.22(14) . . . . ? C27 N11 C12 N13 167.77(11) . . . . ? C15 N11 C12 C31 -178.08(11) . . . . ? C27 N11 C12 C31 -10.1(2) . . . . ? N11 C12 N13 C14 0.20(14) . . . . ? C31 C12 N13 C14 178.06(12) . . . . ? C12 N13 C14 C15 -0.11(15) . . . . ? N13 C14 C15 N11 -0.02(15) . . . . ? C12 N11 C15 C14 0.14(14) . . . . ? C27 N11 C15 C14 -168.26(11) . . . . ? C26 N21 C22 C23 -0.6(2) . . . . ? N21 C22 C23 C24 1.8(2) . . . . ? N21 C22 C23 C27 -176.24(13) . . . . ? C22 C23 C24 C25 -1.1(2) . . . . ? C27 C23 C24 C25 176.76(14) . . . . ? C23 C24 C25 C26 -0.6(2) . . . . ? C22 N21 C26 C25 -1.3(2) . . . . ? C24 C25 C26 N21 1.8(2) . . . . ? C12 N11 C27 C23 107.33(14) . . . . ? C15 N11 C27 C23 -86.59(16) . . . . ? C22 C23 C27 N11 -175.69(12) . . . . ? C24 C23 C27 N11 6.4(2) . . . . ? N13 C12 C31 C32 136.92(14) . . . . ? N11 C12 C31 C32 -45.52(19) . . . . ? N13 C12 C31 C36 -42.92(19) . . . . ? N11 C12 C31 C36 134.64(13) . . . . ? C36 C31 C32 C33 -1.1(2) . . . . ? C12 C31 C32 C33 179.07(13) . . . . ? C31 C32 C33 C34 -0.2(2) . . . . ? C32 C33 C34 C35 0.8(2) . . . . ? C33 C34 C35 C36 0.0(2) . . . . ? C34 C35 C36 C31 -1.3(2) . . . . ? C32 C31 C36 C35 1.9(2) . . . . ? C12 C31 C36 C35 -178.29(12) . . . . ? C46 C41 C42 C43 0.8(2) . . . . ? C47 C41 C42 C43 179.64(13) . . . . ? C41 C42 C43 C44 -0.4(2) . . . . ? C42 C43 C44 O44 179.15(13) . . . . ? C42 C43 C44 C45 -0.6(2) . . . . ? O44 C44 C45 C46 -178.52(12) . . . . ? C43 C44 C45 C46 1.2(2) . . . . ? C44 C45 C46 C41 -0.9(2) . . . . ? C42 C41 C46 C45 -0.1(2) . . . . ? C47 C41 C46 C45 -179.00(12) . . . . ? C42 C41 C47 N47 169.23(13) . . . . ? C46 C41 C47 N47 -11.9(2) . . . . ? C42 C41 C47 C48 -13.2(2) . . . . ? C46 C41 C47 C48 165.63(13) . . . . ? C48 C47 N47 O47 2.57(19) . . . . ? C41 C47 N47 O47 -179.88(12) . . . . ? N47 C47 C48 N48 60(3) . . . . ? C41 C47 C48 N48 -118(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 O44 H44 N13 1.016(19) 1.665(19) 2.6685(16) 168.5(16) . O47 H47 N21 0.959(19) 1.70(2) 2.6536(16) 176.3(16) 4_766 _diffrn_measured_fraction_theta_max 0.904 _diffrn_reflns_theta_full 69.60 _diffrn_measured_fraction_theta_full 0.903 _refine_diff_density_max 0.254 _refine_diff_density_min -0.277 _refine_diff_density_rms 0.070 _database_code_depnum_ccdc_archive 'CCDC 910344' ####################################################################### # # 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_PhOx:3 #TrackingRef 'combined.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic "KEPC11 4-HO-PhC(CN)=NOH, 4,4'-bipyridyl-1-oxide" _chemical_name_common ? _chemical_formula_moiety '(C8 H6 N2 O2) (C10 H8 N2 O)' _chemical_formula_sum 'C18 H14 N4 O3' _chemical_melting_point ? _exptl_crystal_description prism _exptl_crystal_colour colourless _diffrn_ambient_temperature 120(2) _chemical_formula_weight 334.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 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' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.5844(4) _cell_length_b 12.3410(9) _cell_length_c 12.6218(10) _cell_angle_alpha 69.286(4) _cell_angle_beta 89.334(5) _cell_angle_gamma 78.144(5) _cell_volume 794.50(10) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2515 _cell_measurement_theta_min 3.75 _cell_measurement_theta_max 68.22 _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.398 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 0.813 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8043 _exptl_absorpt_correction_T_max 0.9378 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_radiation_probe ? _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 8990 _diffrn_reflns_av_R_equivalents 0.0448 _diffrn_reflns_av_sigmaI/netI 0.0456 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.75 _diffrn_reflns_theta_max 69.35 _reflns_number_total 2716 _reflns_number_gt 2251 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0800P)^2^+0.1000P] 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_number_reflns 2716 _refine_ls_number_parameters 232 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0561 _refine_ls_R_factor_gt 0.0466 _refine_ls_wR_factor_ref 0.1372 _refine_ls_wR_factor_gt 0.1273 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.082 _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 C11 C 0.7925(3) 0.54161(14) 0.21742(14) 0.0285(4) Uani 1 1 d . . . C12 C 0.6044(3) 0.49307(15) 0.19317(14) 0.0296(4) Uani 1 1 d . . . H12 H 0.5526 0.5107 0.1163 0.036 Uiso 1 1 calc R . . C13 C 0.4927(3) 0.41995(15) 0.27904(15) 0.0312(4) Uani 1 1 d . . . H13 H 0.3648 0.3878 0.2612 0.037 Uiso 1 1 calc R . . C14 C 0.5672(4) 0.39335(16) 0.39157(15) 0.0337(4) Uani 1 1 d . . . O14 O 0.4637(3) 0.32132(12) 0.47919(11) 0.0438(4) Uani 1 1 d . . . H14 H 0.388(4) 0.275(2) 0.454(2) 0.053 Uiso 1 1 d . . . C15 C 0.7543(4) 0.44114(16) 0.41700(15) 0.0373(5) Uani 1 1 d . . . H15 H 0.8052 0.4235 0.4939 0.045 Uiso 1 1 calc R . . C16 C 0.8657(4) 0.51388(16) 0.33097(15) 0.0345(4) Uani 1 1 d . . . H16 H 0.9940 0.5456 0.3492 0.041 Uiso 1 1 calc R . . C17 C 0.9012(3) 0.62551(14) 0.12565(14) 0.0290(4) Uani 1 1 d . . . N17 N 1.0331(3) 0.68996(13) 0.14925(13) 0.0339(4) Uani 1 1 d . . . O17 O 1.1172(2) 0.76479(11) 0.05436(11) 0.0391(3) Uani 1 1 d . . . H17 H 1.198(4) 0.814(2) 0.0884(19) 0.047 Uiso 1 1 d . . . C18 C 0.8483(3) 0.63686(15) 0.01007(15) 0.0337(4) Uani 1 1 d . . . N18 N 0.7989(3) 0.64600(15) -0.08069(14) 0.0456(5) Uani 1 1 d . . . N21 N 0.1680(3) 0.11549(13) 0.38209(12) 0.0301(4) Uani 1 1 d . . . O21 O 0.3195(2) 0.15641(11) 0.42906(12) 0.0418(4) Uani 1 1 d . . . C22 C 0.2028(3) -0.00301(15) 0.40750(14) 0.0299(4) Uani 1 1 d . . . H22 H 0.3376 -0.0548 0.4575 0.036 Uiso 1 1 calc R . . C23 C 0.0449(3) -0.04892(15) 0.36159(14) 0.0290(4) Uani 1 1 d . . . H23 H 0.0718 -0.1323 0.3803 0.035 Uiso 1 1 calc R . . C24 C -0.1548(3) 0.02522(14) 0.28776(13) 0.0276(4) Uani 1 1 d . . . C25 C -0.1832(3) 0.14653(15) 0.26375(15) 0.0317(4) Uani 1 1 d . . . H25 H -0.3170 0.2002 0.2142 0.038 Uiso 1 1 calc R . . C26 C -0.0215(3) 0.18999(15) 0.31034(15) 0.0321(4) Uani 1 1 d . . . H26 H -0.0432 0.2731 0.2919 0.038 Uiso 1 1 calc R . . N31 N -0.6589(3) -0.11573(13) 0.14667(12) 0.0351(4) Uani 1 1 d . . . C32 C -0.6577(4) -0.00004(17) 0.10689(16) 0.0379(5) Uani 1 1 d . . . H32 H -0.7726 0.0512 0.0461 0.045 Uiso 1 1 calc R . . C33 C -0.4987(4) 0.04905(16) 0.14935(15) 0.0357(4) Uani 1 1 d . . . H33 H -0.5052 0.1319 0.1177 0.043 Uiso 1 1 calc R . . C34 C -0.3285(3) -0.02357(15) 0.23904(13) 0.0281(4) Uani 1 1 d . . . C35 C -0.3343(3) -0.14375(15) 0.28180(15) 0.0322(4) Uani 1 1 d . . . H35 H -0.2244 -0.1971 0.3438 0.039 Uiso 1 1 calc R . . C36 C -0.4993(3) -0.18495(16) 0.23413(15) 0.0347(4) Uani 1 1 d . . . H36 H -0.4999 -0.2671 0.2651 0.042 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 C11 0.0304(9) 0.0267(8) 0.0304(9) -0.0142(7) -0.0025(7) -0.0031(7) C12 0.0309(9) 0.0312(9) 0.0280(8) -0.0139(7) -0.0048(7) -0.0029(7) C13 0.0300(9) 0.0323(9) 0.0331(9) -0.0142(7) -0.0025(7) -0.0061(7) C14 0.0421(11) 0.0317(9) 0.0299(9) -0.0143(7) 0.0039(8) -0.0081(7) O14 0.0632(10) 0.0452(8) 0.0310(7) -0.0150(6) 0.0071(6) -0.0264(7) C15 0.0495(12) 0.0403(10) 0.0274(9) -0.0162(8) -0.0037(8) -0.0133(8) C16 0.0403(11) 0.0357(9) 0.0332(9) -0.0173(8) -0.0047(8) -0.0110(8) C17 0.0287(9) 0.0290(9) 0.0311(9) -0.0143(7) -0.0033(7) -0.0036(7) N17 0.0323(8) 0.0311(8) 0.0387(8) -0.0129(6) 0.0013(6) -0.0068(6) O17 0.0438(8) 0.0413(7) 0.0350(7) -0.0119(6) 0.0013(6) -0.0184(6) C18 0.0377(10) 0.0321(9) 0.0326(10) -0.0117(7) 0.0020(8) -0.0101(7) N18 0.0606(12) 0.0457(10) 0.0340(9) -0.0139(7) -0.0003(8) -0.0194(8) N21 0.0288(8) 0.0334(8) 0.0310(7) -0.0138(6) 0.0032(6) -0.0088(6) O21 0.0380(8) 0.0367(7) 0.0543(8) -0.0183(6) -0.0107(6) -0.0117(6) C22 0.0281(9) 0.0306(9) 0.0295(9) -0.0102(7) 0.0026(7) -0.0039(7) C23 0.0294(9) 0.0292(9) 0.0293(8) -0.0122(7) 0.0057(7) -0.0059(7) C24 0.0298(9) 0.0303(9) 0.0248(8) -0.0123(7) 0.0057(7) -0.0068(7) C25 0.0311(10) 0.0309(9) 0.0322(9) -0.0117(7) -0.0019(7) -0.0039(7) C26 0.0331(10) 0.0268(9) 0.0356(9) -0.0111(7) 0.0016(7) -0.0052(7) N31 0.0347(9) 0.0398(9) 0.0364(8) -0.0183(7) 0.0051(7) -0.0122(7) C32 0.0370(11) 0.0408(10) 0.0343(10) -0.0096(8) -0.0033(8) -0.0115(8) C33 0.0395(11) 0.0316(9) 0.0350(9) -0.0093(8) 0.0003(8) -0.0105(8) C34 0.0279(9) 0.0321(9) 0.0263(8) -0.0130(7) 0.0061(7) -0.0060(7) C35 0.0325(10) 0.0304(9) 0.0344(9) -0.0137(7) 0.0010(7) -0.0045(7) C36 0.0361(10) 0.0321(9) 0.0397(10) -0.0172(8) 0.0065(8) -0.0082(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 C11 C16 1.396(3) . ? C11 C12 1.397(2) . ? C11 C17 1.475(2) . ? C12 C13 1.379(2) . ? C12 H12 0.9500 . ? C13 C14 1.388(3) . ? C13 H13 0.9500 . ? C14 O14 1.359(2) . ? C14 C15 1.392(3) . ? O14 H14 0.92(3) . ? C15 C16 1.377(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 N17 1.295(2) . ? C17 C18 1.443(3) . ? N17 O17 1.3749(19) . ? O17 H17 1.03(2) . ? C18 N18 1.142(2) . ? N21 O21 1.3118(19) . ? N21 C26 1.349(2) . ? N21 C22 1.354(2) . ? C22 C23 1.373(2) . ? C22 H22 0.9500 . ? C23 C24 1.396(2) . ? C23 H23 0.9500 . ? C24 C25 1.393(2) . ? C24 C34 1.483(2) . ? C25 C26 1.372(3) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? N31 C36 1.336(2) . ? N31 C32 1.337(2) . ? C32 C33 1.380(3) . ? C32 H32 0.9500 . ? C33 C34 1.395(3) . ? C33 H33 0.9500 . ? C34 C35 1.395(2) . ? C35 C36 1.376(3) . ? C35 H35 0.9500 . ? C36 H36 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 C16 C11 C12 118.32(17) . . ? C16 C11 C17 120.74(16) . . ? C12 C11 C17 120.84(15) . . ? C13 C12 C11 121.01(16) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C12 C13 C14 120.01(17) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? O14 C14 C13 122.23(17) . . ? O14 C14 C15 118.16(16) . . ? C13 C14 C15 119.61(17) . . ? C14 O14 H14 109.9(14) . . ? C16 C15 C14 120.18(16) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C15 C16 C11 120.86(18) . . ? C15 C16 H16 119.6 . . ? C11 C16 H16 119.6 . . ? N17 C17 C18 121.51(16) . . ? N17 C17 C11 120.06(15) . . ? C18 C17 C11 118.38(15) . . ? C17 N17 O17 112.86(14) . . ? N17 O17 H17 101.4(12) . . ? N18 C18 C17 177.9(2) . . ? O21 N21 C26 120.69(14) . . ? O21 N21 C22 119.08(14) . . ? C26 N21 C22 120.23(15) . . ? N21 C22 C23 120.57(16) . . ? N21 C22 H22 119.7 . . ? C23 C22 H22 119.7 . . ? C22 C23 C24 120.92(15) . . ? C22 C23 H23 119.5 . . ? C24 C23 H23 119.5 . . ? C25 C24 C23 116.58(16) . . ? C25 C24 C34 122.06(16) . . ? C23 C24 C34 121.35(15) . . ? C26 C25 C24 121.24(16) . . ? C26 C25 H25 119.4 . . ? C24 C25 H25 119.4 . . ? N21 C26 C25 120.46(15) . . ? N21 C26 H26 119.8 . . ? C25 C26 H26 119.8 . . ? C36 N31 C32 116.73(16) . . ? N31 C32 C33 123.60(17) . . ? N31 C32 H32 118.2 . . ? C33 C32 H32 118.2 . . ? C32 C33 C34 119.67(17) . . ? C32 C33 H33 120.2 . . ? C34 C33 H33 120.2 . . ? C35 C34 C33 116.46(17) . . ? C35 C34 C24 121.93(16) . . ? C33 C34 C24 121.60(15) . . ? C36 C35 C34 119.89(17) . . ? C36 C35 H35 120.1 . . ? C34 C35 H35 120.1 . . ? N31 C36 C35 123.62(16) . . ? N31 C36 H36 118.2 . . ? C35 C36 H36 118.2 . . ? 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 C16 C11 C12 C13 0.3(2) . . . . ? C17 C11 C12 C13 -176.26(15) . . . . ? C11 C12 C13 C14 -0.2(3) . . . . ? C12 C13 C14 O14 -179.68(16) . . . . ? C12 C13 C14 C15 0.2(3) . . . . ? O14 C14 C15 C16 179.53(17) . . . . ? C13 C14 C15 C16 -0.3(3) . . . . ? C14 C15 C16 C11 0.5(3) . . . . ? C12 C11 C16 C15 -0.4(3) . . . . ? C17 C11 C16 C15 176.10(16) . . . . ? C16 C11 C17 N17 -12.1(3) . . . . ? C12 C11 C17 N17 164.32(16) . . . . ? C16 C11 C17 C18 170.38(16) . . . . ? C12 C11 C17 C18 -13.2(2) . . . . ? C18 C17 N17 O17 -1.5(2) . . . . ? C11 C17 N17 O17 -178.94(14) . . . . ? N17 C17 C18 N18 -132(5) . . . . ? C11 C17 C18 N18 46(5) . . . . ? O21 N21 C22 C23 178.71(14) . . . . ? C26 N21 C22 C23 -0.6(2) . . . . ? N21 C22 C23 C24 0.0(2) . . . . ? C22 C23 C24 C25 0.1(2) . . . . ? C22 C23 C24 C34 -179.08(14) . . . . ? C23 C24 C25 C26 0.3(2) . . . . ? C34 C24 C25 C26 179.49(15) . . . . ? O21 N21 C26 C25 -178.29(14) . . . . ? C22 N21 C26 C25 1.0(2) . . . . ? C24 C25 C26 N21 -0.9(3) . . . . ? C36 N31 C32 C33 1.7(3) . . . . ? N31 C32 C33 C34 -0.3(3) . . . . ? C32 C33 C34 C35 -1.1(3) . . . . ? C32 C33 C34 C24 -179.74(15) . . . . ? C25 C24 C34 C35 -165.19(16) . . . . ? C23 C24 C34 C35 14.0(2) . . . . ? C25 C24 C34 C33 13.4(2) . . . . ? C23 C24 C34 C33 -167.42(16) . . . . ? C33 C34 C35 C36 1.1(2) . . . . ? C24 C34 C35 C36 179.76(14) . . . . ? C32 N31 C36 C35 -1.6(3) . . . . ? C34 C35 C36 N31 0.3(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 O14 H14 O21 0.92(3) 1.71(3) 2.6052(19) 163(2) . O17 H17 N31 1.03(2) 1.64(2) 2.665(2) 176(2) 1_765 _diffrn_measured_fraction_theta_max 0.914 _diffrn_reflns_theta_full 66.00 _diffrn_measured_fraction_theta_full 0.949 _refine_diff_density_max 0.203 _refine_diff_density_min -0.344 _refine_diff_density_rms 0.058 _database_code_depnum_ccdc_archive 'CCDC 910345'