# 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_spa14 _database_code_depnum_ccdc_archive 'CCDC 838418' #TrackingRef 'spa14.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H16 N10 O, 2(C2H6O), H2O' _chemical_formula_sum 'C22 H16 N10 O4' _chemical_formula_weight 484.45 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.710(4) _cell_length_b 10.353(5) _cell_length_c 14.973(7) _cell_angle_alpha 107.204(10) _cell_angle_beta 92.640(11) _cell_angle_gamma 94.681(11) _cell_volume 1281.9(11) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1847 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 47.34 _exptl_crystal_description Blocks _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.255 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 500 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9836 _exptl_absorpt_correction_T_max 0.9927 _exptl_absorpt_process_details 'SADABS; Sheldrick, 1997' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex CCD Area Detector' _diffrn_measurement_method 'phi and omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6902 _diffrn_reflns_av_R_equivalents 0.0245 _diffrn_reflns_av_sigmaI/netI 0.0510 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 25.14 _reflns_number_total 4380 _reflns_number_gt 2972 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SAINTPLUS _computing_data_reduction SAINTPLUS _computing_structure_solution 'SHELXTL (Sheldrick, 1990)' _computing_structure_refinement 'SHELXTL (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^)+(0.1000P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4380 _refine_ls_number_parameters 340 _refine_ls_number_restraints 299 _refine_ls_R_factor_all 0.0895 _refine_ls_R_factor_gt 0.0642 _refine_ls_wR_factor_ref 0.1953 _refine_ls_wR_factor_gt 0.1826 _refine_ls_goodness_of_fit_ref 1.194 _refine_ls_restrained_S_all 1.172 _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 0.4653(2) 1.42826(16) 0.59175(11) 0.0462(5) Uani 1 1 d U . . O200 O 0.8268(3) 1.0160(2) 0.86470(19) 0.0990(9) Uani 1 1 d U . . N8 N 0.6720(2) 1.36376(19) 0.72331(14) 0.0386(5) Uani 1 1 d U . . N9 N 0.7950(3) 1.1696(2) 0.69516(16) 0.0540(6) Uani 1 1 d U . . H9B H 0.8320 1.1039 0.7130 0.065 Uiso 1 1 calc R . . H9A H 0.8039 1.1725 0.6375 0.065 Uiso 1 1 calc R . . N10 N 0.7142(3) 1.2569(2) 0.84296(14) 0.0461(6) Uani 1 1 d U . . N11 N 0.6270(3) 1.3540(2) 0.98819(15) 0.0614(7) Uani 1 1 d U . . H11A H 0.6670 1.2910 1.0078 0.074 Uiso 1 1 calc R . . H11B H 0.5789 1.4165 1.0269 0.074 Uiso 1 1 calc R . . N12 N 0.5737(2) 1.4543(2) 0.87363(14) 0.0433(5) Uani 1 1 d U . . N20 N 0.1601(2) 0.82802(19) 0.50493(14) 0.0383(5) Uani 1 1 d U . . N21 N 0.1244(3) 0.5974(2) 0.43634(15) 0.0502(6) Uani 1 1 d U . . H22A H 0.0802 0.5161 0.4322 0.060 Uiso 1 1 calc R . . H21A H 0.1933 0.6069 0.3970 0.060 Uiso 1 1 calc R . . N22 N -0.0184(2) 0.6898(2) 0.56183(14) 0.0422(5) Uani 1 1 d U . . N23 N -0.1583(3) 0.7948(2) 0.68505(18) 0.0616(7) Uani 1 1 d U . . H23A H -0.2086 0.7155 0.6802 0.074 Uiso 1 1 calc R . . H23B H -0.1802 0.8681 0.7282 0.074 Uiso 1 1 calc R . . N24 N 0.0232(2) 0.9300(2) 0.63874(14) 0.0423(5) Uani 1 1 d U . . C1 C 0.4676(3) 1.5488(2) 0.66459(17) 0.0373(6) Uani 1 1 d U . . C2 C 0.5335(3) 1.5649(2) 0.75514(16) 0.0365(6) Uani 1 1 d U . . C3 C 0.5407(3) 1.6948(2) 0.82004(18) 0.0459(7) Uani 1 1 d U . . H3 H 0.5845 1.7089 0.8819 0.055 Uiso 1 1 calc R . . C4 C 0.4860(4) 1.8032(3) 0.7966(2) 0.0569(8) Uani 1 1 d U . . H4 H 0.4938 1.8907 0.8416 0.068 Uiso 1 1 calc R . . C5 C 0.4196(4) 1.7834(3) 0.7071(2) 0.0582(8) Uani 1 1 d U . . H5 H 0.3800 1.8571 0.6911 0.070 Uiso 1 1 calc R . . C6 C 0.4110(3) 1.6577(3) 0.64152(19) 0.0492(7) Uani 1 1 d U . . H6 H 0.3662 1.6449 0.5801 0.059 Uiso 1 1 calc R . . C7 C 0.5965(3) 1.4527(2) 0.78527(17) 0.0373(6) Uani 1 1 d U . . C9 C 0.7252(3) 1.2652(2) 0.75578(17) 0.0397(6) Uani 1 1 d U . . C11 C 0.6393(3) 1.3549(3) 0.89990(18) 0.0439(6) Uani 1 1 d U . . C13 C 0.3787(3) 1.3124(2) 0.59442(16) 0.0387(6) Uani 1 1 d U . . C14 C 0.4112(4) 1.1956(3) 0.5293(2) 0.0613(9) Uani 1 1 d U . . H14 H 0.4907 1.1987 0.4884 0.074 Uiso 1 1 calc R . . C15 C 0.3285(4) 1.0734(3) 0.5231(2) 0.0577(8) Uani 1 1 d U . . H15 H 0.3515 0.9927 0.4778 0.069 Uiso 1 1 calc R . . C16 C 0.2113(3) 1.0668(2) 0.58269(17) 0.0379(6) Uani 1 1 d U . . C17 C 0.1816(3) 1.1872(3) 0.6481(2) 0.0480(7) Uani 1 1 d U . . H17 H 0.1027 1.1854 0.6895 0.058 Uiso 1 1 calc R . . C18 C 0.2647(3) 1.3100(3) 0.65398(19) 0.0478(7) Uani 1 1 d U . . H18 H 0.2427 1.3914 0.6989 0.057 Uiso 1 1 calc R . . C19 C 0.1266(3) 0.9347(2) 0.57521(16) 0.0355(6) Uani 1 1 d U . . C21 C 0.0868(3) 0.7067(2) 0.50255(17) 0.0374(6) Uani 1 1 d U . . C23 C -0.0479(3) 0.8040(2) 0.62645(18) 0.0413(6) Uani 1 1 d U . . O10A O 0.1717(10) 1.0083(10) 0.8440(7) 0.086(4) Uiso 0.291(9) 1 d PU A 2 O100 O 0.1388(10) 1.0645(9) 0.9521(8) 0.245(6) Uani 0.709(9) 1 d PU A 1 C102 C 0.1992(8) 1.2532(7) 0.9142(5) 0.157(2) Uani 1 1 d U A . C104 C 0.2584(8) 1.1248(6) 0.8917(6) 0.164(3) Uani 1 1 d U . . O10B O 0.994(3) 1.461(3) 1.1607(15) 0.147(11) Uiso 0.32(3) 1 d PU B 2 O101 O 0.9665(19) 1.403(3) 1.1485(13) 0.403(18) Uani 0.68(3) 1 d PU B 1 C10A C 0.8897(14) 1.3372(14) 1.1691(8) 0.076(4) Uiso 0.417(18) 1 d PU B 2 C103 C 0.9104(16) 1.241(3) 1.1071(17) 0.170(7) Uani 0.583(18) 1 d PU B 1 C105 C 0.8436(6) 1.2183(6) 1.0761(3) 0.0772(13) Uani 1 1 d U . . 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 0.0617(12) 0.0359(9) 0.0394(10) 0.0127(8) 0.0073(9) -0.0109(8) O200 0.130(2) 0.0704(16) 0.102(2) 0.0267(14) 0.0199(17) 0.0316(16) N8 0.0437(12) 0.0348(11) 0.0395(12) 0.0124(9) 0.0112(10) 0.0069(9) N9 0.0728(17) 0.0458(13) 0.0508(14) 0.0187(11) 0.0226(12) 0.0234(12) N10 0.0556(14) 0.0461(12) 0.0416(12) 0.0166(10) 0.0123(10) 0.0160(11) N11 0.0881(19) 0.0686(16) 0.0402(13) 0.0252(12) 0.0183(12) 0.0399(14) N12 0.0523(14) 0.0455(12) 0.0361(12) 0.0147(10) 0.0107(10) 0.0151(10) N20 0.0395(12) 0.0325(11) 0.0430(12) 0.0116(9) 0.0103(9) -0.0005(9) N21 0.0641(16) 0.0311(11) 0.0542(14) 0.0096(10) 0.0233(12) -0.0012(10) N22 0.0443(13) 0.0347(11) 0.0492(13) 0.0144(10) 0.0158(10) 0.0002(10) N23 0.0674(17) 0.0425(13) 0.0769(17) 0.0170(12) 0.0403(14) 0.0013(12) N24 0.0438(13) 0.0371(12) 0.0467(12) 0.0128(10) 0.0137(10) 0.0018(10) C1 0.0394(14) 0.0320(13) 0.0415(14) 0.0140(11) 0.0070(11) -0.0045(11) C2 0.0384(14) 0.0343(13) 0.0394(14) 0.0142(11) 0.0107(11) 0.0029(11) C3 0.0535(17) 0.0425(14) 0.0412(14) 0.0101(12) 0.0062(12) 0.0083(12) C4 0.074(2) 0.0339(14) 0.0635(19) 0.0115(13) 0.0167(16) 0.0124(14) C5 0.069(2) 0.0474(17) 0.069(2) 0.0302(15) 0.0118(16) 0.0183(15) C6 0.0525(17) 0.0493(16) 0.0511(16) 0.0246(13) -0.0003(13) 0.0010(13) C7 0.0380(14) 0.0354(13) 0.0385(14) 0.0113(11) 0.0061(11) 0.0017(11) C9 0.0397(15) 0.0396(14) 0.0429(14) 0.0152(12) 0.0129(11) 0.0059(11) C11 0.0490(16) 0.0453(14) 0.0412(14) 0.0168(12) 0.0086(12) 0.0095(12) C13 0.0432(15) 0.0361(13) 0.0389(14) 0.0171(11) 0.0001(11) -0.0045(11) C14 0.076(2) 0.0468(16) 0.0540(17) 0.0055(14) 0.0322(16) -0.0153(15) C15 0.068(2) 0.0378(15) 0.0581(18) 0.0013(13) 0.0305(15) -0.0102(14) C16 0.0382(14) 0.0347(13) 0.0413(14) 0.0125(11) 0.0044(11) 0.0023(11) C17 0.0417(16) 0.0384(14) 0.0606(17) 0.0086(13) 0.0215(13) -0.0004(12) C18 0.0462(16) 0.0323(13) 0.0587(17) 0.0037(12) 0.0142(13) 0.0002(12) C19 0.0339(14) 0.0361(13) 0.0382(13) 0.0135(11) 0.0045(11) 0.0036(11) C21 0.0396(15) 0.0312(12) 0.0419(14) 0.0123(11) 0.0043(11) 0.0013(11) C23 0.0402(15) 0.0367(14) 0.0499(15) 0.0165(12) 0.0120(12) 0.0029(11) O100 0.217(8) 0.232(9) 0.343(14) 0.203(10) -0.069(7) -0.040(6) C102 0.181(6) 0.128(4) 0.154(5) 0.025(4) 0.003(4) 0.036(4) C104 0.158(6) 0.087(4) 0.233(7) 0.035(4) -0.033(5) -0.002(4) O101 0.296(18) 0.330(16) 0.41(3) -0.095(17) -0.129(16) -0.092(15) C103 0.110(11) 0.209(12) 0.25(2) 0.142(14) -0.002(8) 0.064(9) C105 0.077(4) 0.094(3) 0.071(3) 0.038(2) -0.011(2) 0.028(3) _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 C13 1.375(3) . ? O1 C1 1.392(3) . ? N8 C7 1.338(3) . ? N8 C9 1.357(3) . ? N9 C9 1.338(3) . ? N10 C9 1.341(3) . ? N10 C11 1.353(3) . ? N11 C11 1.334(3) . ? N12 C7 1.343(3) . ? N12 C11 1.361(3) . ? N20 C19 1.344(3) . ? N20 C21 1.352(3) . ? N21 C21 1.341(3) . ? N22 C23 1.340(3) . ? N22 C21 1.341(3) . ? N23 C23 1.348(3) . ? N24 C19 1.348(3) . ? N24 C23 1.354(3) . ? C1 C6 1.392(3) . ? C1 C2 1.405(3) . ? C2 C3 1.402(3) . ? C2 C7 1.498(3) . ? C3 C4 1.384(4) . ? C4 C5 1.385(4) . ? C5 C6 1.373(4) . ? C13 C18 1.369(4) . ? C13 C14 1.370(4) . ? C14 C15 1.380(4) . ? C15 C16 1.397(4) . ? C16 C17 1.391(3) . ? C16 C19 1.472(3) . ? C17 C18 1.387(4) . ? O10A C104 1.351(10) . ? O100 C104 1.615(11) . ? C102 C104 1.418(8) . ? O10B C10A 1.55(3) . ? O101 C103 1.63(4) . ? C10A C105 1.572(15) . ? C103 C105 0.706(18) . ? 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 C13 O1 C1 120.79(18) . . ? C7 N8 C9 114.1(2) . . ? C9 N10 C11 114.9(2) . . ? C7 N12 C11 114.0(2) . . ? C19 N20 C21 115.3(2) . . ? C23 N22 C21 115.1(2) . . ? C19 N24 C23 113.6(2) . . ? O1 C1 C6 116.3(2) . . ? O1 C1 C2 122.6(2) . . ? C6 C1 C2 120.9(2) . . ? C3 C2 C1 117.1(2) . . ? C3 C2 C7 118.9(2) . . ? C1 C2 C7 124.0(2) . . ? C4 C3 C2 121.9(2) . . ? C3 C4 C5 119.5(3) . . ? C6 C5 C4 120.2(2) . . ? C5 C6 C1 120.3(2) . . ? N8 C7 N12 126.6(2) . . ? N8 C7 C2 117.6(2) . . ? N12 C7 C2 115.7(2) . . ? N9 C9 N10 118.0(2) . . ? N9 C9 N8 116.6(2) . . ? N10 C9 N8 125.4(2) . . ? N11 C11 N10 117.9(2) . . ? N11 C11 N12 117.2(2) . . ? N10 C11 N12 124.9(2) . . ? C18 C13 C14 120.9(2) . . ? C18 C13 O1 124.5(2) . . ? C14 C13 O1 114.6(2) . . ? C13 C14 C15 120.0(3) . . ? C14 C15 C16 120.8(2) . . ? C17 C16 C15 117.7(2) . . ? C17 C16 C19 122.8(2) . . ? C15 C16 C19 119.5(2) . . ? C18 C17 C16 121.4(2) . . ? C13 C18 C17 119.2(2) . . ? N20 C19 N24 125.5(2) . . ? N20 C19 C16 116.5(2) . . ? N24 C19 C16 118.0(2) . . ? N21 C21 N22 119.0(2) . . ? N21 C21 N20 116.7(2) . . ? N22 C21 N20 124.3(2) . . ? N22 C23 N23 118.0(2) . . ? N22 C23 N24 126.0(2) . . ? N23 C23 N24 116.0(2) . . ? O10A C104 C102 122.5(7) . . ? O10A C104 O100 64.5(6) . . ? C102 C104 O100 93.9(7) . . ? O10B C10A C105 116.7(10) . . ? C105 C103 O101 120(2) . . ? C103 C105 C10A 44(2) . . ? _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_theta_full 25.14 _diffrn_measured_fraction_theta_full 0.952 _refine_diff_density_max 0.390 _refine_diff_density_min -0.227 _refine_diff_density_rms 0.056 data_datam_2 _database_code_depnum_ccdc_archive 'CCDC 838419' #TrackingRef 'spa20.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H16 N10 O, C2 H6 O S, O' _chemical_formula_sum 'C20 H22 N10 O3 S' _chemical_formula_weight 482.54 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3660(10) _cell_length_b 9.9820(10) _cell_length_c 14.679(2) _cell_angle_alpha 91.4650(10) _cell_angle_beta 97.580(3) _cell_angle_gamma 105.924(3) _cell_volume 1166.0(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4347 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 47.34 _exptl_crystal_description Blocks _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.374 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 0.183 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9660 _exptl_absorpt_correction_T_max 0.9837 _exptl_absorpt_process_details 'SADABS; Sheldrick, 1997' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex CCD Area Detector' _diffrn_measurement_method 'phi and omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11398 _diffrn_reflns_av_R_equivalents 0.0641 _diffrn_reflns_av_sigmaI/netI 0.0723 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 25.15 _reflns_number_total 4057 _reflns_number_gt 3033 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SAINTPLUS _computing_data_reduction SAINTPLUS _computing_structure_solution 'SHELXTL (Sheldrick, 1990)' _computing_structure_refinement 'SHELXTL (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^)+(0.1664P)^2^+0.9799P] 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 4057 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1038 _refine_ls_R_factor_gt 0.0862 _refine_ls_wR_factor_ref 0.2577 _refine_ls_wR_factor_gt 0.2387 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _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 S90 S 0.42424(13) 0.43038(12) 0.62296(8) 0.0482(4) Uani 1 1 d . . . O90 O 0.2971(8) 0.3473(7) 0.7073(4) 0.130(2) Uani 1 1 d . . . C91 C 0.3570(6) 0.5851(5) 0.6138(4) 0.0588(13) Uani 1 1 d . . . H91A H 0.4012 0.6453 0.6704 0.088 Uiso 0.50 1 calc PR . . H91B H 0.2340 0.5599 0.6048 0.088 Uiso 0.50 1 calc PR . . H91C H 0.3989 0.6348 0.5613 0.088 Uiso 0.50 1 calc PR . . H91D H 0.2882 0.5814 0.5539 0.088 Uiso 0.50 1 calc PR . . H91E H 0.4554 0.6668 0.6195 0.088 Uiso 0.50 1 calc PR . . H91F H 0.2905 0.5919 0.6630 0.088 Uiso 0.50 1 calc PR . . C92 C 0.3520(4) 0.3441(3) 0.5346(2) 0.0278(8) Uani 1 1 d . . . H92A H 0.3857 0.2575 0.5361 0.042 Uiso 0.50 1 calc PR . . H92B H 0.3937 0.3967 0.4830 0.042 Uiso 0.50 1 calc PR . . H92C H 0.2291 0.3216 0.5267 0.042 Uiso 0.50 1 calc PR . . H92D H 0.2867 0.3930 0.4944 0.042 Uiso 0.50 1 calc PR . . H92E H 0.2787 0.2539 0.5476 0.042 Uiso 0.50 1 calc PR . . H92F H 0.4433 0.3289 0.5038 0.042 Uiso 0.50 1 calc PR . . O100 O 0.0326(4) 0.3264(3) 0.4450(2) 0.0544(8) Uani 1 1 d . . . O1 O 0.5586(3) 0.2164(3) 0.86074(18) 0.0355(6) Uani 1 1 d . . . N8 N 0.6177(4) -0.0133(3) 0.6209(2) 0.0382(8) Uani 1 1 d . . . N9 N 0.7580(5) -0.0431(4) 0.5001(3) 0.0537(10) Uani 1 1 d . . . H9B H 0.8275 -0.0098 0.4607 0.064 Uiso 1 1 calc R . . H9A H 0.7120 -0.1336 0.5000 0.064 Uiso 1 1 calc R . . N10 N 0.7957(4) 0.1812(4) 0.5576(2) 0.0400(8) Uani 1 1 d . . . N11 N 0.8385(4) 0.4011(4) 0.6277(2) 0.0451(9) Uani 1 1 d . . . H11A H 0.9126 0.4352 0.5909 0.054 Uiso 1 1 calc R . . H11B H 0.8166 0.4569 0.6687 0.054 Uiso 1 1 calc R . . N12 N 0.6483(4) 0.2183(3) 0.6813(2) 0.0343(7) Uani 1 1 d . . . N20 N 0.8145(4) 0.5819(3) 0.7917(2) 0.0333(7) Uani 1 1 d . . . N21 N 0.7914(5) 0.7684(4) 0.7065(2) 0.0494(9) Uani 1 1 d . . . H21B H 0.7476 0.8376 0.6938 0.059 Uiso 1 1 calc R . . H21A H 0.8652 0.7514 0.6736 0.059 Uiso 1 1 calc R . . N22 N 0.6321(4) 0.7200(4) 0.8239(2) 0.0398(8) Uani 1 1 d . . . N23 N 0.4700(5) 0.6558(4) 0.9387(2) 0.0519(10) Uani 1 1 d . . . H23A H 0.4301 0.7277 0.9280 0.062 Uiso 1 1 calc R . . H23B H 0.4353 0.6001 0.9819 0.062 Uiso 1 1 calc R . . N24 N 0.6393(4) 0.5179(3) 0.9083(2) 0.0341(7) Uani 1 1 d . . . C1 C 0.4576(4) 0.0845(4) 0.8286(3) 0.0337(8) Uani 1 1 d . . . C2 C 0.3415(5) 0.0179(5) 0.8843(3) 0.0403(10) Uani 1 1 d . . . H2 H 0.3418 0.0608 0.9428 0.048 Uiso 1 1 calc R . . C3 C 0.2255(5) -0.1096(5) 0.8563(3) 0.0447(10) Uani 1 1 d . . . H3 H 0.1480 -0.1535 0.8957 0.054 Uiso 1 1 calc R . . C4 C 0.2229(5) -0.1728(4) 0.7707(3) 0.0446(10) Uani 1 1 d . . . H4 H 0.1424 -0.2592 0.7501 0.054 Uiso 1 1 calc R . . C5 C 0.3406(5) -0.1073(4) 0.7154(3) 0.0390(9) Uani 1 1 d . . . H5 H 0.3395 -0.1510 0.6570 0.047 Uiso 1 1 calc R . . C6 C 0.4605(4) 0.0205(4) 0.7426(2) 0.0322(8) Uani 1 1 d . . . C7 C 0.5833(5) 0.0808(4) 0.6778(3) 0.0343(9) Uani 1 1 d . . . C9 C 0.7218(5) 0.0454(4) 0.5611(3) 0.0360(9) Uani 1 1 d . . . C11 C 0.7595(5) 0.2648(4) 0.6214(2) 0.0341(9) Uani 1 1 d . . . C13 C 0.7328(4) 0.2422(4) 0.8759(2) 0.0311(8) Uani 1 1 d . . . C14 C 0.8289(4) 0.3823(4) 0.8766(2) 0.0327(9) Uani 1 1 d . . . C15 C 1.0043(5) 0.4095(5) 0.8925(3) 0.0417(10) Uani 1 1 d . . . H14A H 1.0729 0.5028 0.8931 0.050 Uiso 1 1 calc R . . C16 C 1.0793(5) 0.3025(5) 0.9073(3) 0.0477(11) Uani 1 1 d . . . H5A H 1.1982 0.3227 0.9180 0.057 Uiso 1 1 calc R . . C17 C 0.9806(6) 0.1672(5) 0.9063(3) 0.0521(12) Uani 1 1 d . . . H2A H 1.0324 0.0943 0.9169 0.063 Uiso 1 1 calc R . . C18 C 0.8052(5) 0.1350(5) 0.8901(3) 0.0426(10) Uani 1 1 d . . . H10A H 0.7376 0.0412 0.8889 0.051 Uiso 1 1 calc R . . C19 C 0.7553(4) 0.5003(4) 0.8578(2) 0.0303(8) Uani 1 1 d . . . C21 C 0.7457(5) 0.6885(4) 0.7762(3) 0.0356(9) Uani 1 1 d . . . C23 C 0.5846(5) 0.6310(4) 0.8886(2) 0.0338(9) 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 S90 0.0398(6) 0.0555(7) 0.0522(7) -0.0058(5) -0.0012(5) 0.0226(5) O90 0.137(5) 0.161(5) 0.104(4) 0.034(4) 0.028(4) 0.052(4) C91 0.059(3) 0.064(3) 0.058(3) -0.009(2) 0.000(2) 0.029(2) C92 0.0316(18) 0.0218(17) 0.0327(18) -0.0069(14) 0.0076(14) 0.0111(14) O100 0.0503(18) 0.069(2) 0.0476(17) 0.0161(15) 0.0182(14) 0.0166(16) O1 0.0314(13) 0.0403(15) 0.0396(14) 0.0019(12) 0.0107(11) 0.0156(12) N8 0.0452(19) 0.0403(19) 0.0347(17) 0.0020(14) 0.0154(14) 0.0168(15) N9 0.073(3) 0.049(2) 0.048(2) 0.0003(17) 0.0319(19) 0.0205(19) N10 0.0466(19) 0.047(2) 0.0318(17) 0.0028(14) 0.0168(14) 0.0161(16) N11 0.050(2) 0.045(2) 0.0427(19) 0.0031(16) 0.0227(16) 0.0110(17) N12 0.0356(16) 0.0390(19) 0.0319(16) 0.0033(14) 0.0122(13) 0.0128(14) N20 0.0321(16) 0.0413(18) 0.0307(16) 0.0036(13) 0.0089(12) 0.0150(14) N21 0.058(2) 0.056(2) 0.049(2) 0.0211(18) 0.0250(17) 0.0293(19) N22 0.0456(19) 0.049(2) 0.0332(17) 0.0057(15) 0.0122(14) 0.0237(16) N23 0.067(2) 0.066(2) 0.046(2) 0.0213(18) 0.0326(18) 0.044(2) N24 0.0345(16) 0.0471(19) 0.0253(15) 0.0017(14) 0.0080(12) 0.0174(15) C1 0.0307(18) 0.039(2) 0.038(2) 0.0065(16) 0.0092(15) 0.0177(16) C2 0.037(2) 0.056(3) 0.035(2) 0.0056(18) 0.0166(16) 0.0199(19) C3 0.038(2) 0.057(3) 0.044(2) 0.011(2) 0.0184(18) 0.013(2) C4 0.034(2) 0.042(2) 0.060(3) 0.007(2) 0.0141(19) 0.0110(18) C5 0.039(2) 0.042(2) 0.040(2) 0.0031(17) 0.0108(17) 0.0147(18) C6 0.0322(18) 0.038(2) 0.0334(19) 0.0074(16) 0.0095(15) 0.0192(16) C7 0.0324(19) 0.043(2) 0.0315(19) 0.0058(16) 0.0055(15) 0.0170(17) C9 0.042(2) 0.042(2) 0.0295(19) 0.0063(16) 0.0111(16) 0.0180(18) C11 0.037(2) 0.042(2) 0.0281(18) 0.0085(16) 0.0081(15) 0.0162(17) C13 0.0290(18) 0.048(2) 0.0220(17) 0.0048(15) 0.0066(13) 0.0193(17) C14 0.0328(19) 0.049(2) 0.0208(16) -0.0001(15) 0.0053(14) 0.0180(17) C15 0.031(2) 0.056(3) 0.039(2) 0.0011(19) 0.0034(16) 0.0145(19) C16 0.031(2) 0.071(3) 0.046(2) 0.003(2) -0.0010(17) 0.024(2) C17 0.051(3) 0.073(3) 0.047(2) 0.009(2) 0.004(2) 0.043(3) C18 0.043(2) 0.054(3) 0.038(2) 0.0076(18) 0.0085(17) 0.023(2) C19 0.0286(17) 0.040(2) 0.0221(16) -0.0043(15) 0.0043(14) 0.0097(16) C21 0.0316(19) 0.044(2) 0.0321(19) 0.0035(16) 0.0086(15) 0.0107(17) C23 0.0366(19) 0.043(2) 0.0261(18) 0.0017(16) 0.0049(15) 0.0189(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 S90 C92 1.497(3) . ? S90 C91 1.785(5) . ? S90 O90 1.808(6) . ? O1 C1 1.387(5) . ? O1 C13 1.395(4) . ? N8 C9 1.349(5) . ? N8 C7 1.355(5) . ? N9 C9 1.361(5) . ? N10 C9 1.331(5) . ? N10 C11 1.357(5) . ? N11 C11 1.334(5) . ? N12 C7 1.328(5) . ? N12 C11 1.361(5) . ? N20 C19 1.341(5) . ? N20 C21 1.353(5) . ? N21 C21 1.343(5) . ? N22 C23 1.341(5) . ? N22 C21 1.350(5) . ? N23 C23 1.352(5) . ? N24 C19 1.340(5) . ? N24 C23 1.354(5) . ? C1 C2 1.391(5) . ? C1 C6 1.407(5) . ? C2 C3 1.385(6) . ? C3 C4 1.387(6) . ? C4 C5 1.393(6) . ? C5 C6 1.399(5) . ? C6 C7 1.506(5) . ? C13 C18 1.374(6) . ? C13 C14 1.408(6) . ? C14 C15 1.403(5) . ? C14 C19 1.487(5) . ? C15 C16 1.387(6) . ? C16 C17 1.375(7) . ? C17 C18 1.400(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C92 S90 C91 106.3(2) . . ? C92 S90 O90 105.5(3) . . ? C91 S90 O90 99.0(3) . . ? C1 O1 C13 119.9(3) . . ? C9 N8 C7 113.6(3) . . ? C9 N10 C11 114.8(3) . . ? C7 N12 C11 115.1(3) . . ? C19 N20 C21 114.7(3) . . ? C23 N22 C21 113.8(3) . . ? C19 N24 C23 114.0(3) . . ? O1 C1 C2 116.4(3) . . ? O1 C1 C6 123.9(3) . . ? C2 C1 C6 119.7(4) . . ? C3 C2 C1 121.6(4) . . ? C2 C3 C4 119.8(4) . . ? C3 C4 C5 118.8(4) . . ? C4 C5 C6 122.5(4) . . ? C5 C6 C1 117.7(3) . . ? C5 C6 C7 118.0(3) . . ? C1 C6 C7 124.3(3) . . ? N12 C7 N8 125.9(3) . . ? N12 C7 C6 118.5(3) . . ? N8 C7 C6 115.6(3) . . ? N10 C9 N8 126.3(3) . . ? N10 C9 N9 117.0(3) . . ? N8 C9 N9 116.7(4) . . ? N11 C11 N10 118.8(3) . . ? N11 C11 N12 117.1(3) . . ? N10 C11 N12 124.1(3) . . ? C18 C13 O1 120.9(4) . . ? C18 C13 C14 122.3(3) . . ? O1 C13 C14 116.8(3) . . ? C15 C14 C13 117.2(3) . . ? C15 C14 C19 119.0(4) . . ? C13 C14 C19 123.8(3) . . ? C16 C15 C14 121.2(4) . . ? C17 C16 C15 119.7(4) . . ? C16 C17 C18 121.1(4) . . ? C13 C18 C17 118.5(4) . . ? N24 C19 N20 125.7(3) . . ? N24 C19 C14 118.4(3) . . ? N20 C19 C14 115.9(3) . . ? N21 C21 N22 117.0(4) . . ? N21 C21 N20 117.6(3) . . ? N22 C21 N20 125.4(3) . . ? N22 C23 N23 116.9(3) . . ? N22 C23 N24 126.3(3) . . ? N23 C23 N24 116.7(3) . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 25.15 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.978 _refine_diff_density_min -0.526 _refine_diff_density_rms 0.104 data_a _database_code_depnum_ccdc_archive 'CCDC 838420' #TrackingRef 'spa31.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H16 N10 O' _chemical_formula_sum 'C18 H16 N10 O' _chemical_formula_weight 388.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.9692(18) _cell_length_b 10.621(2) _cell_length_c 14.453(3) _cell_angle_alpha 83.86(3) _cell_angle_beta 85.29(3) _cell_angle_gamma 77.44(3) _cell_volume 1333.7(5) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6238 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 47.34 _exptl_crystal_description Blocks _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 0.967 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 404 _exptl_absorpt_coefficient_mu 0.067 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9841 _exptl_absorpt_correction_T_max 0.9914 _exptl_absorpt_process_details 'SADABS; Sheldrick, 1997' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex CCD Area Detector' _diffrn_measurement_method 'phi and omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13131 _diffrn_reflns_av_R_equivalents 0.0388 _diffrn_reflns_av_sigmaI/netI 0.0527 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 24.99 _reflns_number_total 4643 _reflns_number_gt 3766 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SAINTPLUS _computing_data_reduction SAINTPLUS _computing_structure_solution 'SHELXTL (Sheldrick, 1990)' _computing_structure_refinement 'SHELXTL (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^)+(0.0741P)^2^+1.9548P] 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 4643 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0823 _refine_ls_R_factor_gt 0.0716 _refine_ls_wR_factor_ref 0.1805 _refine_ls_wR_factor_gt 0.1759 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 0.1017(2) 0.81906(18) 0.73640(12) 0.0200(4) Uani 1 1 d . . . N8 N 0.0993(2) 0.5830(2) 1.16591(14) 0.0183(5) Uani 1 1 d . . . N9 N 0.1518(3) 0.4622(2) 1.30549(16) 0.0276(6) Uani 1 1 d . . . H9A H 0.2132 0.4025 1.2745 0.033 Uiso 1 1 calc R . . H9B H 0.1399 0.4506 1.3666 0.033 Uiso 1 1 calc R . . N10 N -0.0146(2) 0.6583(2) 1.31188(14) 0.0182(5) Uani 1 1 d . . . N11 N -0.1719(3) 0.8610(2) 1.30748(15) 0.0219(5) Uani 1 1 d . . . H11A H -0.1838 0.8521 1.3687 0.026 Uiso 1 1 calc R . . H11B H -0.2181 0.9325 1.2761 0.026 Uiso 1 1 calc R . . N12 N -0.0687(2) 0.7890(2) 1.16840(15) 0.0190(5) Uani 1 1 d . . . N20 N 0.5629(2) 0.7136(2) 0.79878(15) 0.0173(5) Uani 1 1 d . . . N21 N 0.7453(2) 0.6824(2) 0.90516(15) 0.0208(5) Uani 1 1 d . . . H21B H 0.7857 0.7063 0.9522 0.025 Uiso 1 1 calc R . . H21A H 0.7889 0.6101 0.8806 0.025 Uiso 1 1 calc R . . N22 N 0.5553(2) 0.8656(2) 0.91056(15) 0.0189(5) Uani 1 1 d . . . N23 N 0.3577(3) 1.0443(2) 0.90819(16) 0.0244(5) Uani 1 1 d . . . H23A H 0.3959 1.0694 0.9556 0.029 Uiso 1 1 calc R . . H23B H 0.2739 1.0915 0.8847 0.029 Uiso 1 1 calc R . . N24 N 0.3632(2) 0.9019(2) 0.79882(15) 0.0175(5) Uani 1 1 d . . . C1 C 0.0926(3) 0.7811(2) 0.83036(17) 0.0167(5) Uani 1 1 d . . . C2 C 0.1493(3) 0.6570(3) 0.86970(18) 0.0204(6) Uani 1 1 d . . . H2 H 0.2022 0.5918 0.8317 0.024 Uiso 1 1 calc R . . C3 C 0.1280(3) 0.6289(3) 0.96554(18) 0.0211(6) Uani 1 1 d . . . H3 H 0.1686 0.5441 0.9927 0.025 Uiso 1 1 calc R . . C4 C 0.0489(3) 0.7215(2) 1.02213(17) 0.0164(5) Uani 1 1 d . . . C5 C -0.0082(3) 0.8469(2) 0.98044(18) 0.0181(5) Uani 1 1 d . . . H5 H -0.0621 0.9122 1.0181 0.022 Uiso 1 1 calc R . . C6 C 0.0131(3) 0.8760(2) 0.88577(18) 0.0187(5) Uani 1 1 d . . . H6 H -0.0265 0.9608 0.8584 0.022 Uiso 1 1 calc R . . C7 C 0.0244(3) 0.6955(2) 1.12488(17) 0.0161(5) Uani 1 1 d . . . C9 C 0.0762(3) 0.5710(2) 1.25949(18) 0.0187(5) Uani 1 1 d . . . C11 C -0.0836(3) 0.7661(3) 1.26223(17) 0.0173(5) Uani 1 1 d . . . C13 C 0.2170(3) 0.7549(2) 0.67743(17) 0.0179(5) Uani 1 1 d . . . C14 C 0.1665(3) 0.7063(3) 0.60317(18) 0.0227(6) Uani 1 1 d . . . H26A H 0.0607 0.7084 0.5996 0.027 Uiso 1 1 calc R . . C15 C 0.2723(3) 0.6544(3) 0.53386(19) 0.0260(6) Uani 1 1 d . . . H25A H 0.2385 0.6222 0.4823 0.031 Uiso 1 1 calc R . . C16 C 0.4263(3) 0.6497(3) 0.54008(18) 0.0231(6) Uani 1 1 d . . . H24A H 0.4982 0.6166 0.4920 0.028 Uiso 1 1 calc R . . C17 C 0.4749(3) 0.6933(2) 0.61617(19) 0.0198(5) Uani 1 1 d . . . H0AA H 0.5814 0.6866 0.6212 0.024 Uiso 1 1 calc R . . C18 C 0.3718(3) 0.7472(2) 0.68612(17) 0.0159(5) Uani 1 1 d . . . C19 C 0.4352(3) 0.7910(2) 0.76655(16) 0.0143(5) Uani 1 1 d . . . C21 C 0.6164(3) 0.7569(2) 0.87061(18) 0.0182(5) Uani 1 1 d . . . C23 C 0.4266(3) 0.9352(2) 0.87224(18) 0.0165(5) 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 O1 0.0152(9) 0.0275(10) 0.0125(9) 0.0021(7) 0.0004(7) 0.0037(7) N8 0.0185(11) 0.0154(11) 0.0166(11) 0.0002(8) -0.0013(8) 0.0052(8) N9 0.0350(14) 0.0242(12) 0.0142(11) 0.0003(9) 0.0061(10) 0.0104(10) N10 0.0173(11) 0.0184(11) 0.0156(11) 0.0017(8) -0.0001(8) 0.0014(9) N11 0.0268(12) 0.0223(12) 0.0109(10) -0.0017(8) 0.0032(9) 0.0055(9) N12 0.0177(11) 0.0174(11) 0.0190(11) 0.0017(9) 0.0002(9) 0.0007(9) N20 0.0133(10) 0.0162(11) 0.0206(11) -0.0017(8) -0.0025(8) 0.0014(8) N21 0.0176(11) 0.0211(11) 0.0225(11) -0.0114(9) -0.0064(9) 0.0049(9) N22 0.0157(11) 0.0164(11) 0.0232(11) -0.0043(9) -0.0035(9) 0.0020(9) N23 0.0202(12) 0.0255(12) 0.0269(12) -0.0108(10) -0.0131(9) 0.0046(9) N24 0.0165(11) 0.0179(11) 0.0175(11) -0.0040(8) -0.0031(8) -0.0004(9) C1 0.0124(12) 0.0236(13) 0.0147(12) 0.0014(10) -0.0006(9) -0.0066(10) C2 0.0209(13) 0.0177(13) 0.0204(13) -0.0063(10) 0.0014(10) 0.0021(10) C3 0.0252(14) 0.0198(13) 0.0154(12) 0.0021(10) -0.0061(10) 0.0013(11) C4 0.0134(12) 0.0180(13) 0.0177(13) -0.0057(10) 0.0030(9) -0.0024(10) C5 0.0170(12) 0.0159(12) 0.0191(13) -0.0051(10) 0.0043(10) 0.0011(10) C6 0.0207(13) 0.0135(12) 0.0200(13) -0.0015(10) -0.0004(10) 0.0002(10) C7 0.0140(12) 0.0141(12) 0.0193(13) -0.0047(10) 0.0026(9) -0.0008(10) C9 0.0212(13) 0.0149(12) 0.0187(13) -0.0019(10) -0.0022(10) -0.0003(10) C11 0.0134(12) 0.0228(13) 0.0155(12) -0.0062(10) 0.0017(9) -0.0021(10) C13 0.0196(13) 0.0172(12) 0.0152(12) -0.0015(10) 0.0012(10) -0.0011(10) C14 0.0217(14) 0.0255(14) 0.0206(13) 0.0022(11) -0.0058(11) -0.0045(11) C15 0.0382(16) 0.0220(14) 0.0195(13) -0.0040(11) -0.0040(12) -0.0080(12) C16 0.0354(16) 0.0172(13) 0.0143(12) -0.0048(10) 0.0019(11) -0.0003(11) C17 0.0155(12) 0.0168(12) 0.0247(14) -0.0022(10) 0.0019(10) 0.0008(10) C18 0.0175(12) 0.0126(12) 0.0142(12) 0.0002(9) -0.0002(10) 0.0031(9) C19 0.0132(12) 0.0155(12) 0.0125(11) -0.0002(9) 0.0051(9) -0.0020(9) C21 0.0143(12) 0.0182(13) 0.0211(13) -0.0016(10) -0.0028(10) -0.0011(10) C23 0.0165(12) 0.0118(12) 0.0200(12) -0.0055(9) 0.0006(10) 0.0014(10) _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 C1 1.376(3) . ? O1 C13 1.390(3) . ? N8 C7 1.340(3) . ? N8 C9 1.348(3) . ? N9 C9 1.344(3) . ? N9 H9A 0.8800 . ? N9 H9B 0.8800 . ? N10 C11 1.341(3) . ? N10 C9 1.348(3) . ? N11 C11 1.334(3) . ? N11 H11A 0.8800 . ? N11 H11B 0.8800 . ? N12 C7 1.329(3) . ? N12 C11 1.353(3) . ? N20 C21 1.342(3) . ? N20 C19 1.342(3) . ? N21 C21 1.351(3) . ? N21 H21B 0.8800 . ? N21 H21A 0.8800 . ? N22 C21 1.335(3) . ? N22 C23 1.353(3) . ? N23 C23 1.326(3) . ? N23 H23A 0.8800 . ? N23 H23B 0.8800 . ? N24 C19 1.326(3) . ? N24 C23 1.357(3) . ? C1 C2 1.383(4) . ? C1 C6 1.390(4) . ? C2 C3 1.392(4) . ? C2 H2 0.9500 . ? C3 C4 1.383(4) . ? C3 H3 0.9500 . ? C4 C5 1.407(4) . ? C4 C7 1.488(3) . ? C5 C6 1.377(4) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C13 C14 1.387(4) . ? C13 C18 1.388(4) . ? C14 C15 1.394(4) . ? C14 H26A 0.9500 . ? C15 C16 1.381(4) . ? C15 H25A 0.9500 . ? C16 C17 1.375(4) . ? C16 H24A 0.9500 . ? C17 C18 1.395(4) . ? C17 H0AA 0.9500 . ? C18 C19 1.494(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C13 121.1(2) . . ? C7 N8 C9 114.0(2) . . ? C9 N9 H9A 120.0 . . ? C9 N9 H9B 120.0 . . ? H9A N9 H9B 120.0 . . ? C11 N10 C9 113.7(2) . . ? C11 N11 H11A 120.0 . . ? C11 N11 H11B 120.0 . . ? H11A N11 H11B 120.0 . . ? C7 N12 C11 115.2(2) . . ? C21 N20 C19 113.9(2) . . ? C21 N21 H21B 120.0 . . ? C21 N21 H21A 120.0 . . ? H21B N21 H21A 120.0 . . ? C21 N22 C23 114.0(2) . . ? C23 N23 H23A 120.0 . . ? C23 N23 H23B 120.0 . . ? H23A N23 H23B 120.0 . . ? C19 N24 C23 114.9(2) . . ? O1 C1 C2 124.5(2) . . ? O1 C1 C6 115.1(2) . . ? C2 C1 C6 120.3(2) . . ? C1 C2 C3 119.3(2) . . ? C1 C2 H2 120.4 . . ? C3 C2 H2 120.4 . . ? C4 C3 C2 121.5(2) . . ? C4 C3 H3 119.3 . . ? C2 C3 H3 119.3 . . ? C3 C4 C5 118.2(2) . . ? C3 C4 C7 123.1(2) . . ? C5 C4 C7 118.7(2) . . ? C6 C5 C4 120.8(2) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C1 119.9(2) . . ? C5 C6 H6 120.0 . . ? C1 C6 H6 120.0 . . ? N12 C7 N8 125.6(2) . . ? N12 C7 C4 116.2(2) . . ? N8 C7 C4 118.2(2) . . ? N9 C9 N8 117.2(2) . . ? N9 C9 N10 116.5(2) . . ? N8 C9 N10 126.3(2) . . ? N11 C11 N10 118.7(2) . . ? N11 C11 N12 116.1(2) . . ? N10 C11 N12 125.2(2) . . ? C14 C13 C18 121.1(2) . . ? C14 C13 O1 115.0(2) . . ? C18 C13 O1 123.7(2) . . ? C13 C14 C15 119.4(3) . . ? C13 C14 H26A 120.3 . . ? C15 C14 H26A 120.3 . . ? C16 C15 C14 120.1(3) . . ? C16 C15 H25A 120.0 . . ? C14 C15 H25A 120.0 . . ? C17 C16 C15 119.7(3) . . ? C17 C16 H24A 120.2 . . ? C15 C16 H24A 120.2 . . ? C16 C17 C18 121.6(2) . . ? C16 C17 H0AA 119.2 . . ? C18 C17 H0AA 119.2 . . ? C13 C18 C17 118.0(2) . . ? C13 C18 C19 124.1(2) . . ? C17 C18 C19 117.8(2) . . ? N24 C19 N20 126.0(2) . . ? N24 C19 C18 118.1(2) . . ? N20 C19 C18 116.0(2) . . ? N22 C21 N20 126.5(2) . . ? N22 C21 N21 117.4(2) . . ? N20 C21 N21 116.1(2) . . ? N23 C23 N22 118.0(2) . . ? N23 C23 N24 117.4(2) . . ? N22 C23 N24 124.6(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 C13 O1 C1 C2 -26.0(4) . . . . ? C13 O1 C1 C6 157.4(2) . . . . ? O1 C1 C2 C3 -177.5(2) . . . . ? C6 C1 C2 C3 -1.0(4) . . . . ? C1 C2 C3 C4 1.2(4) . . . . ? C2 C3 C4 C5 -1.0(4) . . . . ? C2 C3 C4 C7 -179.6(2) . . . . ? C3 C4 C5 C6 0.6(4) . . . . ? C7 C4 C5 C6 179.3(2) . . . . ? C4 C5 C6 C1 -0.4(4) . . . . ? O1 C1 C6 C5 177.4(2) . . . . ? C2 C1 C6 C5 0.6(4) . . . . ? C11 N12 C7 N8 1.4(4) . . . . ? C11 N12 C7 C4 -177.0(2) . . . . ? C9 N8 C7 N12 -1.7(4) . . . . ? C9 N8 C7 C4 176.7(2) . . . . ? C3 C4 C7 N12 -172.4(2) . . . . ? C5 C4 C7 N12 9.0(3) . . . . ? C3 C4 C7 N8 9.1(4) . . . . ? C5 C4 C7 N8 -169.5(2) . . . . ? C7 N8 C9 N9 -177.9(2) . . . . ? C7 N8 C9 N10 1.5(4) . . . . ? C11 N10 C9 N9 178.3(2) . . . . ? C11 N10 C9 N8 -1.0(4) . . . . ? C9 N10 C11 N11 -177.6(2) . . . . ? C9 N10 C11 N12 0.7(4) . . . . ? C7 N12 C11 N11 177.5(2) . . . . ? C7 N12 C11 N10 -0.9(4) . . . . ? C1 O1 C13 C14 123.6(3) . . . . ? C1 O1 C13 C18 -61.3(3) . . . . ? C18 C13 C14 C15 -3.0(4) . . . . ? O1 C13 C14 C15 172.3(2) . . . . ? C13 C14 C15 C16 1.0(4) . . . . ? C14 C15 C16 C17 1.8(4) . . . . ? C15 C16 C17 C18 -2.6(4) . . . . ? C14 C13 C18 C17 2.3(4) . . . . ? O1 C13 C18 C17 -172.6(2) . . . . ? C14 C13 C18 C19 -176.7(2) . . . . ? O1 C13 C18 C19 8.5(4) . . . . ? C16 C17 C18 C13 0.6(4) . . . . ? C16 C17 C18 C19 179.5(2) . . . . ? C23 N24 C19 N20 -1.3(4) . . . . ? C23 N24 C19 C18 179.6(2) . . . . ? C21 N20 C19 N24 0.5(4) . . . . ? C21 N20 C19 C18 179.6(2) . . . . ? C13 C18 C19 N24 -42.3(3) . . . . ? C17 C18 C19 N24 138.8(2) . . . . ? C13 C18 C19 N20 138.6(2) . . . . ? C17 C18 C19 N20 -40.3(3) . . . . ? C23 N22 C21 N20 0.1(4) . . . . ? C23 N22 C21 N21 179.9(2) . . . . ? C19 N20 C21 N22 0.1(4) . . . . ? C19 N20 C21 N21 -179.7(2) . . . . ? C21 N22 C23 N23 179.5(2) . . . . ? C21 N22 C23 N24 -1.0(4) . . . . ? C19 N24 C23 N23 -178.9(2) . . . . ? C19 N24 C23 N22 1.6(4) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.297 _refine_diff_density_min -0.317 _refine_diff_density_rms 0.062 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.006 -0.011 0.489 528 238 ' ' _platon_squeeze_details ; ; data_w _database_code_depnum_ccdc_archive 'CCDC 838421' #TrackingRef 'spa84.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H16 N10 O, H2 O' _chemical_formula_sum 'C18 H18 N10 O2' _chemical_formula_weight 406.42 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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.882(4) _cell_length_b 7.619(2) _cell_length_c 17.176(4) _cell_angle_alpha 90.00 _cell_angle_beta 115.635(5) _cell_angle_gamma 90.00 _cell_volume 1873.8(8) _cell_formula_units_Z 4 _cell_measurement_temperature 571(2) _cell_measurement_reflns_used 3276 _cell_measurement_theta_min 2.89 _cell_measurement_theta_max 47.89 _exptl_crystal_description Blocks _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.441 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9729 _exptl_absorpt_correction_T_max 0.9868 _exptl_absorpt_process_details 'SADABS; Sheldrick, 1997' _exptl_special_details ; ? ; _diffrn_ambient_temperature 571(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 CCD Area Detector' _diffrn_measurement_method 'phi and omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10566 _diffrn_reflns_av_R_equivalents 0.0775 _diffrn_reflns_av_sigmaI/netI 0.0715 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.42 _diffrn_reflns_theta_max 25.05 _reflns_number_total 3290 _reflns_number_gt 2069 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SAINTPLUS _computing_data_reduction SAINTPLUS _computing_structure_solution 'SHELXTL (Sheldrick, 1990)' _computing_structure_refinement 'SHELXTL (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^)+(0.0472P)^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 3290 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0824 _refine_ls_R_factor_gt 0.0489 _refine_ls_wR_factor_ref 0.1084 _refine_ls_wR_factor_gt 0.0981 _refine_ls_goodness_of_fit_ref 0.903 _refine_ls_restrained_S_all 0.903 _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 0.41371(10) 0.5769(2) 0.38449(9) 0.0484(5) Uani 1 1 d . . . N8 N 0.06325(12) 0.7391(2) 0.46293(11) 0.0357(5) Uani 1 1 d . . . N9 N -0.07844(14) 0.8387(3) 0.45097(14) 0.0452(6) Uani 1 1 d . . . N10 N 0.01534(13) 0.6948(2) 0.57548(12) 0.0409(5) Uani 1 1 d . . . N11 N 0.11381(18) 0.5478(3) 0.69633(14) 0.0537(7) Uani 1 1 d . . . N12 N 0.16414(13) 0.5896(2) 0.59136(11) 0.0400(5) Uani 1 1 d . . . N20 N 0.38264(12) 0.4651(2) 0.00435(11) 0.0372(5) Uani 1 1 d . . . N21 N 0.41003(17) 0.4744(3) -0.11614(16) 0.0520(6) Uani 1 1 d . . . N22 N 0.26586(13) 0.3775(2) -0.13415(11) 0.0362(5) Uani 1 1 d . . . N23 N 0.12762(14) 0.2686(3) -0.14232(14) 0.0457(6) Uani 1 1 d . . . N24 N 0.23388(12) 0.3694(2) -0.01085(11) 0.0346(5) Uani 1 1 d . . . C1 C 0.34303(15) 0.5900(3) 0.41197(14) 0.0374(6) Uani 1 1 d . . . C2 C 0.25691(17) 0.6574(3) 0.36019(16) 0.0452(7) Uani 1 1 d . . . C3 C 0.19218(17) 0.6789(3) 0.39316(15) 0.0424(6) Uani 1 1 d . . . C4 C 0.21255(15) 0.6318(3) 0.47785(13) 0.0347(5) Uani 1 1 d . . . C5 C 0.29972(16) 0.5617(3) 0.52770(15) 0.0400(6) Uani 1 1 d . . . C6 C 0.36495(17) 0.5407(3) 0.49543(15) 0.0427(6) Uani 1 1 d . . . C7 C 0.14270(15) 0.6557(3) 0.51304(14) 0.0337(5) Uani 1 1 d . . . C9 C 0.00181(16) 0.7559(3) 0.49792(14) 0.0362(5) Uani 1 1 d . . . C11 C 0.09729(16) 0.6134(3) 0.61914(14) 0.0375(6) Uani 1 1 d . . . C13 C 0.38938(15) 0.5399(3) 0.29805(13) 0.0371(6) Uani 1 1 d . . . C14 C 0.43298(17) 0.6330(3) 0.25744(15) 0.0406(6) Uani 1 1 d . . . C15 C 0.41171(16) 0.5966(3) 0.17250(15) 0.0391(6) Uani 1 1 d . . . C16 C 0.34731(14) 0.4668(3) 0.12758(13) 0.0331(5) Uani 1 1 d . . . C17 C 0.30656(16) 0.3707(3) 0.17122(14) 0.0373(6) Uani 1 1 d . . . C18 C 0.32713(17) 0.4078(3) 0.25579(15) 0.0399(6) Uani 1 1 d . . . C19 C 0.31987(15) 0.4327(3) 0.03463(13) 0.0312(5) Uani 1 1 d . . . C21 C 0.35071(15) 0.4376(3) -0.08126(13) 0.0355(6) Uani 1 1 d . . . C23 C 0.21197(15) 0.3383(3) -0.09466(14) 0.0334(5) Uani 1 1 d . . . H2 H 0.2424(15) 0.690(3) 0.3059(15) 0.049(7) Uiso 1 1 d . . . H3 H 0.1296(17) 0.730(3) 0.3568(14) 0.053(7) Uiso 1 1 d . . . H5 H 0.3154(14) 0.528(3) 0.5845(14) 0.040(6) Uiso 1 1 d . . . H6 H 0.4213(16) 0.494(3) 0.5291(14) 0.045(7) Uiso 1 1 d . . . H9A H -0.0896(17) 0.885(3) 0.3928(16) 0.064(8) Uiso 1 1 d . . . H9B H -0.1213(17) 0.848(3) 0.4684(14) 0.045(7) Uiso 1 1 d . . . H11A H 0.072(2) 0.562(4) 0.7117(17) 0.064(9) Uiso 1 1 d . . . H11B H 0.169(2) 0.496(3) 0.7266(16) 0.069(9) Uiso 1 1 d . . . H14 H 0.4745(16) 0.726(3) 0.2853(14) 0.055(7) Uiso 1 1 d . . . H15 H 0.4379(15) 0.668(3) 0.1422(13) 0.039(6) Uiso 1 1 d . . . H17 H 0.2646(14) 0.273(3) 0.1431(12) 0.032(6) Uiso 1 1 d . . . H18 H 0.2973(15) 0.340(3) 0.2826(14) 0.043(6) Uiso 1 1 d . . . H21A H 0.478(2) 0.499(4) -0.0748(19) 0.101(10) Uiso 1 1 d . . . H21B H 0.3883(17) 0.461(3) -0.1692(17) 0.060(9) Uiso 1 1 d . . . H23A H 0.1164(14) 0.225(3) -0.1921(14) 0.036(7) Uiso 1 1 d . . . H23B H 0.093(2) 0.231(4) -0.1120(19) 0.083(10) Uiso 1 1 d . . . O90 O -0.01938(14) 0.9224(3) 0.30446(12) 0.0657(6) Uani 1 1 d . . . H90A H 0.020(2) 0.848(4) 0.362(2) 0.112(12) Uiso 1 1 d . . . H90B H 0.002(3) 1.042(6) 0.318(3) 0.18(2) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0307(9) 0.0876(13) 0.0293(9) -0.0047(8) 0.0153(7) 0.0036(8) N8 0.0299(11) 0.0436(11) 0.0374(11) -0.0005(9) 0.0182(9) 0.0038(9) N9 0.0299(13) 0.0653(15) 0.0466(14) 0.0088(11) 0.0222(11) 0.0102(11) N10 0.0353(12) 0.0541(13) 0.0388(11) 0.0049(10) 0.0212(9) 0.0044(10) N11 0.0411(15) 0.0848(18) 0.0409(13) 0.0123(12) 0.0232(12) 0.0124(13) N12 0.0357(11) 0.0517(12) 0.0363(11) 0.0013(9) 0.0191(9) 0.0041(9) N20 0.0330(11) 0.0520(12) 0.0335(11) -0.0025(9) 0.0209(9) -0.0041(9) N21 0.0414(14) 0.0871(18) 0.0377(14) -0.0095(12) 0.0266(12) -0.0156(12) N22 0.0317(11) 0.0473(12) 0.0356(11) -0.0030(9) 0.0201(9) -0.0017(9) N23 0.0395(13) 0.0667(15) 0.0346(12) -0.0091(11) 0.0195(11) -0.0129(11) N24 0.0301(11) 0.0452(12) 0.0319(10) -0.0006(8) 0.0167(9) -0.0022(9) C1 0.0309(13) 0.0504(15) 0.0344(13) -0.0054(11) 0.0174(11) 0.0011(11) C2 0.0422(16) 0.0657(18) 0.0327(14) 0.0084(12) 0.0209(12) 0.0109(13) C3 0.0344(15) 0.0556(16) 0.0386(14) 0.0049(12) 0.0172(12) 0.0124(12) C4 0.0320(13) 0.0395(13) 0.0336(12) -0.0038(10) 0.0152(10) -0.0003(11) C5 0.0373(15) 0.0558(16) 0.0289(13) 0.0004(11) 0.0163(11) 0.0034(12) C6 0.0283(14) 0.0620(17) 0.0342(14) 0.0004(12) 0.0101(11) 0.0079(12) C7 0.0301(13) 0.0375(13) 0.0356(13) -0.0067(10) 0.0163(10) -0.0039(11) C9 0.0323(13) 0.0406(13) 0.0401(13) -0.0027(11) 0.0196(11) -0.0005(11) C11 0.0365(14) 0.0471(14) 0.0325(13) -0.0029(11) 0.0183(11) -0.0007(11) C13 0.0284(13) 0.0551(15) 0.0291(12) 0.0025(11) 0.0137(10) 0.0078(11) C14 0.0363(14) 0.0501(16) 0.0399(14) -0.0082(12) 0.0208(12) -0.0054(12) C15 0.0391(15) 0.0468(15) 0.0411(14) 0.0013(12) 0.0263(12) -0.0029(12) C16 0.0276(12) 0.0412(13) 0.0334(12) 0.0020(10) 0.0159(10) 0.0035(11) C17 0.0312(14) 0.0452(15) 0.0370(13) 0.0021(11) 0.0161(11) -0.0019(11) C18 0.0370(14) 0.0538(16) 0.0363(13) 0.0097(12) 0.0227(12) 0.0019(12) C19 0.0296(13) 0.0346(13) 0.0329(12) 0.0032(10) 0.0168(10) 0.0041(10) C21 0.0336(14) 0.0422(14) 0.0359(13) 0.0012(10) 0.0199(11) 0.0014(11) C23 0.0290(13) 0.0365(13) 0.0365(13) 0.0006(10) 0.0159(10) -0.0003(10) O90 0.0667(14) 0.0745(15) 0.0493(12) 0.0021(11) 0.0189(10) -0.0026(11) _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 C13 1.392(2) . ? O1 C1 1.397(2) . ? N8 C7 1.341(3) . ? N8 C9 1.355(3) . ? N9 C9 1.336(3) . ? N10 C9 1.338(3) . ? N10 C11 1.340(3) . ? N11 C11 1.333(3) . ? N12 C7 1.335(3) . ? N12 C11 1.351(3) . ? N20 C19 1.332(3) . ? N20 C21 1.348(3) . ? N21 C21 1.347(3) . ? N22 C23 1.336(3) . ? N22 C21 1.339(3) . ? N23 C23 1.341(3) . ? N24 C19 1.336(3) . ? N24 C23 1.348(3) . ? C1 C2 1.368(3) . ? C1 C6 1.373(3) . ? C2 C3 1.381(3) . ? C3 C4 1.394(3) . ? C4 C5 1.382(3) . ? C4 C7 1.486(3) . ? C5 C6 1.380(3) . ? C13 C14 1.374(3) . ? C13 C18 1.377(3) . ? C14 C15 1.376(3) . ? C15 C16 1.391(3) . ? C16 C17 1.392(3) . ? C16 C19 1.485(3) . ? C17 C18 1.373(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C13 O1 C1 118.83(16) . . ? C7 N8 C9 114.73(19) . . ? C9 N10 C11 114.63(19) . . ? C7 N12 C11 114.10(18) . . ? C19 N20 C21 113.91(18) . . ? C23 N22 C21 114.20(18) . . ? C19 N24 C23 114.47(18) . . ? C2 C1 C6 120.8(2) . . ? C2 C1 O1 122.1(2) . . ? C6 C1 O1 117.1(2) . . ? C1 C2 C3 119.3(2) . . ? C2 C3 C4 121.3(2) . . ? C5 C4 C3 117.6(2) . . ? C5 C4 C7 121.3(2) . . ? C3 C4 C7 121.1(2) . . ? C6 C5 C4 121.4(2) . . ? C1 C6 C5 119.5(2) . . ? N12 C7 N8 125.8(2) . . ? N12 C7 C4 116.98(19) . . ? N8 C7 C4 117.25(19) . . ? N9 C9 N10 117.8(2) . . ? N9 C9 N8 117.3(2) . . ? N10 C9 N8 124.9(2) . . ? N11 C11 N10 117.1(2) . . ? N11 C11 N12 117.0(2) . . ? N10 C11 N12 125.9(2) . . ? C14 C13 C18 121.0(2) . . ? C14 C13 O1 118.0(2) . . ? C18 C13 O1 121.0(2) . . ? C13 C14 C15 119.2(2) . . ? C14 C15 C16 121.0(2) . . ? C15 C16 C17 118.5(2) . . ? C15 C16 C19 121.6(2) . . ? C17 C16 C19 119.9(2) . . ? C18 C17 C16 120.5(2) . . ? C17 C18 C13 119.7(2) . . ? N20 C19 N24 125.95(19) . . ? N20 C19 C16 117.81(19) . . ? N24 C19 C16 116.24(18) . . ? N22 C21 N21 117.5(2) . . ? N22 C21 N20 125.9(2) . . ? N21 C21 N20 116.6(2) . . ? N22 C23 N23 118.0(2) . . ? N22 C23 N24 125.2(2) . . ? N23 C23 N24 116.7(2) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.215 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.047 data_w _database_code_depnum_ccdc_archive 'CCDC 895838' #TrackingRef 'W.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H18 N10 O2' _chemical_formula_weight 406.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 12.342(3) _cell_length_b 13.853(3) _cell_length_c 14.853(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.91(3) _cell_angle_gamma 90.00 _cell_volume 2484.8(9) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4386 _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 32.5 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.086 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9698 _exptl_absorpt_correction_T_max 0.9878 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'phi and omega scan' _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 14110 _diffrn_reflns_av_R_equivalents 0.0663 _diffrn_reflns_av_sigmaI/netI 0.0519 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4363 _reflns_number_gt 3273 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SAINTPLUS _computing_data_reduction SAINTPLUS _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^)+(0.1205P)^2^+3.2635P] 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 4363 _refine_ls_number_parameters 281 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.1017 _refine_ls_R_factor_gt 0.0843 _refine_ls_wR_factor_ref 0.2339 _refine_ls_wR_factor_gt 0.2246 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.060 _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 0.17245(18) 0.50501(17) 0.30885(15) 0.0265(6) Uani 1 1 d . . . N1 N 0.2880(2) 0.3214(2) 0.12621(17) 0.0237(6) Uani 1 1 d . . . N2 N 0.4482(2) 0.2674(2) 0.23304(18) 0.0224(6) Uani 1 1 d . . . N3 N 0.2906(2) 0.32793(18) 0.28687(17) 0.0189(6) Uani 1 1 d . . . N4 N 0.4383(2) 0.2567(2) 0.07872(19) 0.0322(7) Uani 1 1 d . . . H4A H 0.5053 0.2317 0.0900 0.039 Uiso 1 1 calc R . . H4B H 0.4026 0.2652 0.0215 0.039 Uiso 1 1 calc R . . N5 N 0.4453(2) 0.2743(2) 0.38703(18) 0.0301(7) Uani 1 1 d . . . H5A H 0.5125 0.2497 0.3991 0.036 Uiso 1 1 calc R . . H5B H 0.4120 0.2885 0.4323 0.036 Uiso 1 1 calc R . . N6 N 0.6512(2) 0.6700(2) 0.28956(17) 0.0226(6) Uani 1 1 d . . . N7 N 0.8194(2) 0.7073(2) 0.39582(18) 0.0229(6) Uani 1 1 d . . . N8 N 0.6552(2) 0.66795(19) 0.44980(17) 0.0205(6) Uani 1 1 d . . . N9 N 0.8138(2) 0.6982(2) 0.24174(18) 0.0282(7) Uani 1 1 d . . . H9A H 0.8849 0.7119 0.2531 0.034 Uiso 1 1 calc R . . H9B H 0.7779 0.6886 0.1848 0.034 Uiso 1 1 calc R . . N10 N 0.8155(2) 0.7133(3) 0.54933(19) 0.0364(8) Uani 1 1 d . . . H10A H 0.8853 0.7314 0.5604 0.044 Uiso 1 1 calc R . . H10B H 0.7808 0.7066 0.5951 0.044 Uiso 1 1 calc R . . C11 C 0.1356(3) 0.3956(2) 0.1765(2) 0.0207(7) Uani 1 1 d . . . C12 C 0.1079(3) 0.4754(2) 0.2250(2) 0.0240(7) Uani 1 1 d . . . C13 C 0.0099(3) 0.5237(2) 0.1958(3) 0.0297(8) Uani 1 1 d . . . H13A H -0.0056 0.5791 0.2286 0.036 Uiso 1 1 calc R . . C14 C -0.0670(3) 0.4934(3) 0.1196(3) 0.0356(9) Uani 1 1 d . . . H14A H -0.1344 0.5276 0.1000 0.043 Uiso 1 1 calc R . . C15 C -0.0441(3) 0.4129(3) 0.0728(3) 0.0332(9) Uani 1 1 d . . . H15A H -0.0973 0.3896 0.0218 0.040 Uiso 1 1 calc R . . C16 C 0.0566(3) 0.3654(2) 0.0997(2) 0.0238(7) Uani 1 1 d . . . H16A H 0.0722 0.3112 0.0654 0.029 Uiso 1 1 calc R . . C21 C 0.2438(2) 0.3445(2) 0.1989(2) 0.0184(7) Uani 1 1 d . . . C22 C 0.3907(3) 0.2818(2) 0.1484(2) 0.0217(7) Uani 1 1 d . . . C25 C 0.3940(2) 0.2902(2) 0.3001(2) 0.0185(7) Uani 1 1 d . . . C31 C 0.2763(3) 0.5421(2) 0.3153(2) 0.0219(7) Uani 1 1 d . . . C32 C 0.3390(3) 0.5485(3) 0.4030(2) 0.0345(9) Uani 1 1 d . . . H32A H 0.3096 0.5266 0.4537 0.041 Uiso 1 1 calc R . . C33 C 0.4439(3) 0.5864(3) 0.4176(2) 0.0287(8) Uani 1 1 d . . . H33A H 0.4864 0.5905 0.4786 0.034 Uiso 1 1 calc R . . C34 C 0.4894(3) 0.6191(2) 0.3442(2) 0.0199(7) Uani 1 1 d . . . C35 C 0.4227(3) 0.6137(3) 0.2565(2) 0.0282(8) Uani 1 1 d . . . H35A H 0.4513 0.6364 0.2057 0.034 Uiso 1 1 calc R . . C36 C 0.3175(3) 0.5767(3) 0.2406(2) 0.0283(8) Uani 1 1 d . . . H36A H 0.2735 0.5747 0.1800 0.034 Uiso 1 1 calc R . . C41 C 0.6047(2) 0.6557(2) 0.3620(2) 0.0190(7) Uani 1 1 d . . . C42 C 0.7604(3) 0.6920(2) 0.3107(2) 0.0207(7) Uani 1 1 d . . . C43 C 0.7620(3) 0.6958(2) 0.4628(2) 0.0231(7) Uani 1 1 d . . . O1W O 0.8145(2) 0.7395(4) 0.0538(2) 0.0624(11) Uani 1 1 d DU . . H1 H 0.783(6) 0.792(3) 0.063(6) 0.14(4) Uiso 1 1 d D . . H2 H 0.785(3) 0.713(3) 0.0030(16) 0.044(12) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0198(12) 0.0331(13) 0.0279(12) -0.0087(10) 0.0076(9) -0.0069(10) N1 0.0183(14) 0.0318(16) 0.0200(14) 0.0001(12) 0.0020(11) 0.0036(11) N2 0.0201(14) 0.0270(15) 0.0197(14) 0.0024(11) 0.0030(11) 0.0031(11) N3 0.0154(13) 0.0203(13) 0.0204(13) 0.0021(11) 0.0025(10) -0.0008(10) N4 0.0236(15) 0.053(2) 0.0194(14) -0.0026(13) 0.0021(12) 0.0119(13) N5 0.0202(14) 0.0523(19) 0.0169(14) 0.0012(13) 0.0019(11) 0.0145(13) N6 0.0183(14) 0.0300(15) 0.0197(14) -0.0024(11) 0.0044(11) -0.0076(11) N7 0.0190(13) 0.0283(15) 0.0226(14) -0.0006(12) 0.0071(11) -0.0012(11) N8 0.0153(13) 0.0271(15) 0.0191(13) -0.0022(11) 0.0039(10) 0.0000(10) N9 0.0202(14) 0.0466(18) 0.0190(14) -0.0075(13) 0.0068(11) -0.0106(13) N10 0.0212(15) 0.067(2) 0.0215(14) -0.0062(15) 0.0057(11) -0.0137(15) C11 0.0204(16) 0.0199(16) 0.0202(15) -0.0009(13) 0.0006(12) -0.0020(13) C12 0.0192(16) 0.0218(17) 0.0323(18) -0.0021(14) 0.0082(14) -0.0064(13) C13 0.0204(17) 0.0176(16) 0.051(2) -0.0013(15) 0.0064(15) 0.0028(13) C14 0.0259(19) 0.030(2) 0.048(2) 0.0082(17) 0.0003(16) 0.0074(15) C15 0.0214(18) 0.038(2) 0.036(2) 0.0059(16) -0.0045(15) -0.0018(15) C16 0.0223(17) 0.0223(17) 0.0257(17) 0.0017(13) 0.0022(13) -0.0005(13) C21 0.0168(15) 0.0177(15) 0.0202(16) -0.0023(12) 0.0026(12) -0.0031(12) C22 0.0218(16) 0.0211(16) 0.0228(16) 0.0002(13) 0.0059(13) -0.0011(13) C25 0.0179(15) 0.0223(16) 0.0153(15) -0.0012(12) 0.0035(12) 0.0004(12) C31 0.0199(16) 0.0149(15) 0.0303(18) -0.0074(13) 0.0036(13) -0.0006(12) C32 0.034(2) 0.049(2) 0.0232(18) -0.0076(16) 0.0115(15) -0.0130(17) C33 0.0262(18) 0.043(2) 0.0161(16) -0.0030(15) 0.0030(13) -0.0096(15) C34 0.0193(16) 0.0191(16) 0.0206(16) 0.0031(12) 0.0026(12) -0.0041(12) C35 0.0288(18) 0.037(2) 0.0182(16) 0.0053(15) 0.0039(13) -0.0072(15) C36 0.0262(18) 0.0350(19) 0.0197(16) 0.0077(14) -0.0048(13) -0.0079(15) C41 0.0160(15) 0.0196(16) 0.0213(16) -0.0010(12) 0.0039(12) 0.0010(12) C42 0.0236(16) 0.0190(16) 0.0209(16) -0.0028(13) 0.0076(13) 0.0013(13) C43 0.0217(16) 0.0275(18) 0.0204(16) -0.0015(13) 0.0051(13) 0.0015(13) O1W 0.0277(16) 0.138(4) 0.0204(14) -0.0203(18) 0.0038(11) -0.0166(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C31 1.366(4) . ? O1 C12 1.394(4) . ? N1 C21 1.345(4) . ? N1 C22 1.358(4) . ? N2 C22 1.325(4) . ? N2 C25 1.347(4) . ? N3 C21 1.334(4) . ? N3 C25 1.356(4) . ? N4 C22 1.338(4) . ? N4 H4A 0.8800 . ? N4 H4B 0.8800 . ? N5 C25 1.333(4) . ? N5 H5A 0.8800 . ? N5 H5B 0.8800 . ? N6 C41 1.335(4) . ? N6 C42 1.353(4) . ? N7 C42 1.340(4) . ? N7 C43 1.345(4) . ? N8 C41 1.335(4) . ? N8 C43 1.349(4) . ? N9 C42 1.330(4) . ? N9 H9A 0.8800 . ? N9 H9B 0.8800 . ? N10 C43 1.340(4) . ? N10 H10A 0.8800 . ? N10 H10B 0.8800 . ? C11 C12 1.400(5) . ? C11 C16 1.402(4) . ? C11 C21 1.488(4) . ? C12 C13 1.372(5) . ? C13 C14 1.383(5) . ? C13 H13A 0.9500 . ? C14 C15 1.374(5) . ? C14 H14A 0.9500 . ? C15 C16 1.390(5) . ? C15 H15A 0.9500 . ? C16 H16A 0.9500 . ? C31 C32 1.374(5) . ? C31 C36 1.398(5) . ? C32 C33 1.373(5) . ? C32 H32A 0.9500 . ? C33 C34 1.401(4) . ? C33 H33A 0.9500 . ? C34 C35 1.392(4) . ? C34 C41 1.483(4) . ? C35 C36 1.370(5) . ? C35 H35A 0.9500 . ? C36 H36A 0.9500 . ? O1W H1 0.853(10) . ? O1W H2 0.850(10) . ? loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.089 0.000 0.411 369 131 ' ' 2 -0.131 0.500 0.369 369 131 ' ' _platon_squeeze_details ; ; 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 C31 O1 C12 121.9(2) . . ? C21 N1 C22 114.4(3) . . ? C22 N2 C25 114.6(3) . . ? C21 N3 C25 114.4(3) . . ? C22 N4 H4A 120.0 . . ? C22 N4 H4B 120.0 . . ? H4A N4 H4B 120.0 . . ? C25 N5 H5A 120.0 . . ? C25 N5 H5B 120.0 . . ? H5A N5 H5B 120.0 . . ? C41 N6 C42 114.8(3) . . ? C42 N7 C43 114.3(3) . . ? C41 N8 C43 114.9(3) . . ? C42 N9 H9A 120.0 . . ? C42 N9 H9B 120.0 . . ? H9A N9 H9B 120.0 . . ? C43 N10 H10A 120.0 . . ? C43 N10 H10B 120.0 . . ? H10A N10 H10B 120.0 . . ? C12 C11 C16 116.8(3) . . ? C12 C11 C21 124.3(3) . . ? C16 C11 C21 118.8(3) . . ? C13 C12 O1 116.3(3) . . ? C13 C12 C11 121.0(3) . . ? O1 C12 C11 122.5(3) . . ? C12 C13 C14 121.5(3) . . ? C12 C13 H13A 119.3 . . ? C14 C13 H13A 119.3 . . ? C15 C14 C13 118.8(3) . . ? C15 C14 H14A 120.6 . . ? C13 C14 H14A 120.6 . . ? C14 C15 C16 120.2(3) . . ? C14 C15 H15A 119.9 . . ? C16 C15 H15A 119.9 . . ? C15 C16 C11 121.6(3) . . ? C15 C16 H16A 119.2 . . ? C11 C16 H16A 119.2 . . ? N3 C21 N1 125.5(3) . . ? N3 C21 C11 119.2(3) . . ? N1 C21 C11 115.2(3) . . ? N2 C22 N4 117.4(3) . . ? N2 C22 N1 125.6(3) . . ? N4 C22 N1 117.0(3) . . ? N5 C25 N2 117.9(3) . . ? N5 C25 N3 116.7(3) . . ? N2 C25 N3 125.4(3) . . ? O1 C31 C32 115.3(3) . . ? O1 C31 C36 124.3(3) . . ? C32 C31 C36 120.4(3) . . ? C33 C32 C31 120.2(3) . . ? C33 C32 H32A 119.9 . . ? C31 C32 H32A 119.9 . . ? C32 C33 C34 121.1(3) . . ? C32 C33 H33A 119.4 . . ? C34 C33 H33A 119.4 . . ? C35 C34 C33 117.2(3) . . ? C35 C34 C41 123.1(3) . . ? C33 C34 C41 119.7(3) . . ? C36 C35 C34 122.5(3) . . ? C36 C35 H35A 118.7 . . ? C34 C35 H35A 118.7 . . ? C35 C36 C31 118.6(3) . . ? C35 C36 H36A 120.7 . . ? C31 C36 H36A 120.7 . . ? N6 C41 N8 125.2(3) . . ? N6 C41 C34 117.7(3) . . ? N8 C41 C34 117.0(3) . . ? N9 C42 N7 117.2(3) . . ? N9 C42 N6 117.6(3) . . ? N7 C42 N6 125.2(3) . . ? N10 C43 N7 117.2(3) . . ? N10 C43 N8 117.5(3) . . ? N7 C43 N8 125.2(3) . . ? H1 O1W H2 113(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 C31 O1 C12 C13 -118.1(3) . . . . ? C31 O1 C12 C11 67.4(4) . . . . ? C16 C11 C12 C13 -2.7(5) . . . . ? C21 C11 C12 C13 174.7(3) . . . . ? C16 C11 C12 O1 171.5(3) . . . . ? C21 C11 C12 O1 -11.1(5) . . . . ? O1 C12 C13 C14 -172.2(3) . . . . ? C11 C12 C13 C14 2.4(5) . . . . ? C12 C13 C14 C15 0.3(6) . . . . ? C13 C14 C15 C16 -2.5(5) . . . . ? C14 C15 C16 C11 2.2(5) . . . . ? C12 C11 C16 C15 0.5(5) . . . . ? C21 C11 C16 C15 -177.1(3) . . . . ? C25 N3 C21 N1 4.3(4) . . . . ? C25 N3 C21 C11 -173.4(3) . . . . ? C22 N1 C21 N3 -2.8(5) . . . . ? C22 N1 C21 C11 175.0(3) . . . . ? C12 C11 C21 N3 41.3(4) . . . . ? C16 C11 C21 N3 -141.3(3) . . . . ? C12 C11 C21 N1 -136.6(3) . . . . ? C16 C11 C21 N1 40.8(4) . . . . ? C25 N2 C22 N4 -177.3(3) . . . . ? C25 N2 C22 N1 3.9(5) . . . . ? C21 N1 C22 N2 -1.7(5) . . . . ? C21 N1 C22 N4 179.5(3) . . . . ? C22 N2 C25 N5 177.6(3) . . . . ? C22 N2 C25 N3 -2.0(5) . . . . ? C21 N3 C25 N5 178.6(3) . . . . ? C21 N3 C25 N2 -1.8(4) . . . . ? C12 O1 C31 C32 -166.4(3) . . . . ? C12 O1 C31 C36 16.9(5) . . . . ? O1 C31 C32 C33 -178.8(3) . . . . ? C36 C31 C32 C33 -1.9(5) . . . . ? C31 C32 C33 C34 -0.1(6) . . . . ? C32 C33 C34 C35 1.5(5) . . . . ? C32 C33 C34 C41 -177.3(3) . . . . ? C33 C34 C35 C36 -1.0(5) . . . . ? C41 C34 C35 C36 177.8(3) . . . . ? C34 C35 C36 C31 -0.9(5) . . . . ? O1 C31 C36 C35 178.9(3) . . . . ? C32 C31 C36 C35 2.4(5) . . . . ? C42 N6 C41 N8 4.8(5) . . . . ? C42 N6 C41 C34 -172.3(3) . . . . ? C43 N8 C41 N6 -0.9(5) . . . . ? C43 N8 C41 C34 176.2(3) . . . . ? C35 C34 C41 N6 -10.4(5) . . . . ? C33 C34 C41 N6 168.4(3) . . . . ? C35 C34 C41 N8 172.3(3) . . . . ? C33 C34 C41 N8 -8.9(4) . . . . ? C43 N7 C42 N9 -177.2(3) . . . . ? C43 N7 C42 N6 2.3(5) . . . . ? C41 N6 C42 N9 173.9(3) . . . . ? C41 N6 C42 N7 -5.6(5) . . . . ? C42 N7 C43 N10 -177.9(3) . . . . ? C42 N7 C43 N8 2.4(5) . . . . ? C41 N8 C43 N10 177.2(3) . . . . ? C41 N8 C43 N7 -3.0(5) . . . . ? 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 N4 H4A N7 0.88 2.16 3.014(4) 164.6 2_645 N5 H5A O1W 0.88 2.11 2.953(4) 159.9 2_645 N5 H5B N8 0.88 2.17 3.048(4) 174.1 3_666 N9 H9A N2 0.88 2.17 3.039(4) 170.2 2_655 N9 H9B O1W 0.88 2.20 2.852(4) 130.3 . N10 H10B N3 0.88 2.17 3.045(4) 171.9 3_666 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.483 _refine_diff_density_min -0.296 _refine_diff_density_rms 0.078