# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2012 data_global #TrackingRef '- E-1.cif' _journal_name_full 'New J.Chem.' _journal_coden_cambridge 0440 _publ_contact_author ; Lin Lirong Department of Chemistry Xiamen University Xiamen, 361005 P. R. China ; _publ_contact_author_phone 86-18959284526 _publ_contact_author_fax 86-592-2183047 _publ_contact_author_email linlr@xmu.edu.cn _publ_requested_coeditor_name ? _publ_contact_letter ? _publ_contact_author_name 'Lin Lirong' _publ_author_name L.Lirong # Attachment '- Z-1.cif' data_p _database_code_depnum_ccdc_archive 'CCDC 758818' #TrackingRef '- Z-1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Z-4-phenyl-1-(pyridine-2-ylmethylene)semicarbazide _chemical_melting_point ? _chemical_formula_moiety 'C13 H12 N4 O' _chemical_formula_sum 'C13 H12 N4 O' _chemical_formula_weight 240.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall -P_2ybc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 22.602(8) _cell_length_b 5.5689(19) _cell_length_c 20.209(7) _cell_angle_alpha 90.00 _cell_angle_beta 109.720(6) _cell_angle_gamma 90.00 _cell_volume 2394.5(14) _cell_formula_units_Z 8 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 4676 _cell_measurement_theta_min 1.9 _cell_measurement_theta_max 26.0 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.333 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9566 _exptl_absorpt_correction_T_max 0.9823 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 Smart Apex CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12309 _diffrn_reflns_av_R_equivalents 0.0391 _diffrn_reflns_av_sigmaI/netI 0.0491 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4676 _reflns_number_gt 3375 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL V.5.0 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0609P)^2^+0.7390P] 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 4676 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0999 _refine_ls_R_factor_gt 0.0711 _refine_ls_wR_factor_ref 0.1723 _refine_ls_wR_factor_gt 0.1566 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.17511(11) 0.8851(5) 0.33631(13) 0.0464(6) Uani 1 1 d . . . C2 C 0.16805(13) 1.0591(5) 0.28570(13) 0.0551(7) Uani 1 1 d . . . H2 H 0.1454 1.1981 0.2862 0.066 Uiso 1 1 calc R . . C3 C 0.19490(15) 1.0255(6) 0.23431(14) 0.0628(8) Uani 1 1 d . . . H3 H 0.1896 1.1420 0.1998 0.075 Uiso 1 1 calc R . . C4 C 0.22925(14) 0.8232(6) 0.23319(15) 0.0647(8) Uani 1 1 d . . . H4 H 0.2480 0.8037 0.1991 0.078 Uiso 1 1 calc R . . C5 C 0.23535(14) 0.6502(6) 0.28349(15) 0.0634(8) Uani 1 1 d . . . H5 H 0.2579 0.5111 0.2829 0.076 Uiso 1 1 calc R . . C6 C 0.20863(14) 0.6797(5) 0.33468(15) 0.0591(7) Uani 1 1 d . . . H6 H 0.2131 0.5609 0.3684 0.071 Uiso 1 1 calc R . . C7 C 0.12174(12) 1.0979(5) 0.40885(13) 0.0497(7) Uani 1 1 d . . . C8 C 0.10959(12) 0.8463(5) 0.56376(13) 0.0511(7) Uani 1 1 d . . . H8 H 0.1242 0.7070 0.5895 0.061 Uiso 1 1 calc R . . C9 C 0.07436(12) 1.0074(5) 0.59410(12) 0.0469(6) Uani 1 1 d . . . C10 C 0.06690(13) 0.9460(6) 0.65733(13) 0.0585(8) Uani 1 1 d . . . H10 H 0.0855 0.8081 0.6814 0.070 Uiso 1 1 calc R . . C11 C 0.03127(15) 1.0938(6) 0.68374(14) 0.0691(9) Uani 1 1 d . . . H11 H 0.0248 1.0544 0.7255 0.083 Uiso 1 1 calc R . . C12 C 0.00558(15) 1.2971(6) 0.64849(14) 0.0637(8) Uani 1 1 d . . . H12 H -0.0185 1.3989 0.6657 0.076 Uiso 1 1 calc R . . C13 C 0.01602(14) 1.3482(5) 0.58725(14) 0.0564(7) Uani 1 1 d . . . H13 H -0.0016 1.4876 0.5633 0.068 Uiso 1 1 calc R . . C1A C 0.64769(13) 0.9340(5) 0.82826(14) 0.0503(7) Uani 1 1 d . . . C2A C 0.65614(14) 1.1252(5) 0.87437(16) 0.0619(8) Uani 1 1 d . . . H22A H 0.6280 1.2530 0.8631 0.074 Uiso 1 1 calc R . . C3A C 0.70549(16) 1.1275(6) 0.93630(17) 0.0722(9) Uani 1 1 d . . . H3A H 0.7103 1.2558 0.9671 0.087 Uiso 1 1 calc R . . C4A C 0.74796(16) 0.9424(6) 0.95337(18) 0.0729(9) Uani 1 1 d . . . H4A H 0.7819 0.9459 0.9952 0.087 Uiso 1 1 calc R . . C5A C 0.73991(15) 0.7526(6) 0.90827(17) 0.0699(9) Uani 1 1 d . . . H5A H 0.7682 0.6255 0.9200 0.084 Uiso 1 1 calc R . . C6A C 0.69042(14) 0.7471(5) 0.84571(16) 0.0615(8) Uani 1 1 d . . . H6A H 0.6858 0.6178 0.8152 0.074 Uiso 1 1 calc R . . C7A C 0.57669(16) 0.7747(6) 0.71539(17) 0.0691(9) Uani 1 1 d . . . C8A C 0.45250(15) 1.1190(6) 0.60462(17) 0.0653(8) Uani 1 1 d . . . H8A H 0.4341 1.2654 0.6085 0.078 Uiso 1 1 calc R . . C9A C 0.42674(13) 1.0060(6) 0.53540(15) 0.0568(7) Uani 1 1 d . . . C10A C 0.37833(15) 1.1183(6) 0.48336(19) 0.0717(9) Uani 1 1 d . . . H10A H 0.3610 1.2599 0.4930 0.086 Uiso 1 1 calc R . . C11A C 0.35614(16) 1.0181(7) 0.41713(19) 0.0801(10) Uani 1 1 d . . . H11A H 0.3237 1.0910 0.3815 0.096 Uiso 1 1 calc R . . C12A C 0.38254(16) 0.8102(7) 0.40488(19) 0.0768(10) Uani 1 1 d . . . H12A H 0.3688 0.7396 0.3606 0.092 Uiso 1 1 calc R . . C13A C 0.42960(15) 0.7074(6) 0.45897(17) 0.0673(8) Uani 1 1 d . . . H13A H 0.4472 0.5656 0.4500 0.081 Uiso 1 1 calc R . . N1 N 0.14994(11) 0.9068(4) 0.39134(11) 0.0567(6) Uani 1 1 d . . . H1 H 0.1531 0.7813 0.4171 0.068 Uiso 1 1 calc R . . N2 N 0.10613(10) 1.0678(4) 0.46833(10) 0.0535(6) Uani 1 1 d . . . H7 H 0.0852 1.1776 0.4807 0.064 Uiso 1 1 calc R . . N3 N 0.12351(10) 0.8659(4) 0.50771(11) 0.0528(6) Uani 1 1 d . . . N4 N 0.05002(10) 1.2104(4) 0.55965(10) 0.0498(6) Uani 1 1 d . . . N1A N 0.59610(11) 0.9436(4) 0.76573(13) 0.0620(6) Uani 1 1 d . . . H11N H 0.5742 1.0732 0.7587 0.074 Uiso 1 1 calc R . . N2A N 0.52342(12) 0.8351(5) 0.66087(14) 0.0709(7) Uani 1 1 d . . . H2A H 0.5075 0.7358 0.6269 0.085 Uiso 1 1 calc R . . N3A N 0.49580(12) 1.0517(5) 0.66065(14) 0.0666(7) Uani 1 1 d . . . N4A N 0.45170(11) 0.7972(4) 0.52348(13) 0.0614(6) Uani 1 1 d . . . O1 O 0.10969(10) 1.2868(4) 0.37694(10) 0.0693(6) Uani 1 1 d . . . O2 O 0.60199(12) 0.5827(5) 0.71493(13) 0.0992(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 C1 0.0481(14) 0.0509(16) 0.0456(13) -0.0005(12) 0.0229(11) -0.0024(13) C2 0.0661(18) 0.0518(18) 0.0529(15) 0.0040(14) 0.0270(13) 0.0029(14) C3 0.089(2) 0.0577(19) 0.0528(16) -0.0013(14) 0.0391(15) -0.0091(17) C4 0.073(2) 0.071(2) 0.0652(18) -0.0132(17) 0.0434(16) -0.0178(17) C5 0.072(2) 0.0578(19) 0.0732(19) -0.0092(16) 0.0419(16) 0.0013(16) C6 0.0703(19) 0.0512(18) 0.0656(17) 0.0051(14) 0.0357(15) 0.0032(15) C7 0.0542(16) 0.0522(18) 0.0488(15) 0.0087(13) 0.0253(12) 0.0032(13) C8 0.0560(16) 0.0528(17) 0.0438(14) 0.0085(13) 0.0161(12) 0.0044(13) C9 0.0506(15) 0.0504(16) 0.0376(13) 0.0034(12) 0.0123(11) -0.0064(13) C10 0.0674(18) 0.067(2) 0.0420(14) 0.0065(14) 0.0193(13) -0.0025(15) C11 0.089(2) 0.084(2) 0.0432(15) 0.0008(17) 0.0341(15) -0.0083(19) C12 0.082(2) 0.068(2) 0.0482(16) -0.0096(16) 0.0317(15) -0.0023(17) C13 0.0709(18) 0.0533(18) 0.0481(15) -0.0054(13) 0.0240(14) 0.0002(15) C1A 0.0529(16) 0.0468(17) 0.0598(16) -0.0038(13) 0.0305(13) -0.0047(13) C2A 0.0656(19) 0.0478(18) 0.079(2) -0.0062(15) 0.0337(17) 0.0030(14) C3A 0.083(2) 0.059(2) 0.075(2) -0.0148(17) 0.0265(18) -0.0068(18) C4A 0.074(2) 0.068(2) 0.073(2) -0.0041(18) 0.0199(17) -0.0128(19) C5A 0.067(2) 0.061(2) 0.083(2) 0.0024(18) 0.0278(18) 0.0081(16) C6A 0.0681(19) 0.0514(19) 0.0742(19) -0.0087(15) 0.0362(16) 0.0000(15) C7A 0.071(2) 0.063(2) 0.076(2) -0.0144(18) 0.0284(17) 0.0028(17) C8A 0.067(2) 0.059(2) 0.083(2) -0.0072(17) 0.0425(18) 0.0054(16) C9A 0.0536(16) 0.0566(19) 0.0700(18) 0.0002(15) 0.0339(14) -0.0019(14) C10A 0.069(2) 0.064(2) 0.091(2) 0.0030(19) 0.0386(19) 0.0041(17) C11A 0.068(2) 0.087(3) 0.080(2) 0.009(2) 0.0190(18) 0.007(2) C12A 0.074(2) 0.081(3) 0.077(2) -0.010(2) 0.0265(18) -0.008(2) C13A 0.0651(19) 0.064(2) 0.076(2) -0.0102(18) 0.0279(17) -0.0024(16) N1 0.0724(15) 0.0539(15) 0.0571(13) 0.0156(11) 0.0392(12) 0.0157(12) N2 0.0626(14) 0.0572(15) 0.0484(12) 0.0086(11) 0.0288(11) 0.0124(12) N3 0.0591(14) 0.0567(15) 0.0454(12) 0.0071(11) 0.0215(10) 0.0073(11) N4 0.0590(13) 0.0504(14) 0.0437(11) 0.0007(10) 0.0223(10) -0.0008(11) N1A 0.0673(15) 0.0516(15) 0.0706(15) -0.0126(13) 0.0281(13) 0.0067(12) N2A 0.0750(18) 0.0608(17) 0.0731(17) -0.0153(14) 0.0199(14) 0.0051(14) N3A 0.0671(16) 0.0635(18) 0.0767(17) -0.0113(14) 0.0343(14) 0.0060(14) N4A 0.0605(15) 0.0563(16) 0.0726(16) -0.0091(13) 0.0294(13) -0.0006(12) O1 0.0965(16) 0.0587(14) 0.0717(13) 0.0182(11) 0.0533(12) 0.0182(11) O2 0.1088(19) 0.0722(18) 0.0983(18) -0.0313(14) 0.0111(15) 0.0264(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.378(4) . ? C1 C2 1.379(4) . ? C1 N1 1.415(3) . ? C2 C3 1.381(4) . ? C2 H2 0.9300 . ? C3 C4 1.373(4) . ? C3 H3 0.9300 . ? C4 C5 1.373(4) . ? C4 H4 0.9300 . ? C5 C6 1.373(4) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 O1 1.216(3) . ? C7 N1 1.348(3) . ? C7 N2 1.373(3) . ? C8 N3 1.278(3) . ? C8 C9 1.464(4) . ? C8 H8 0.9300 . ? C9 N4 1.344(3) . ? C9 C10 1.387(3) . ? C10 C11 1.379(4) . ? C10 H10 0.9300 . ? C11 C12 1.360(4) . ? C11 H11 0.9300 . ? C12 C13 1.366(4) . ? C12 H12 0.9300 . ? C13 N4 1.334(3) . ? C13 H13 0.9300 . ? C1A C6A 1.382(4) . ? C1A C2A 1.385(4) . ? C1A N1A 1.402(4) . ? C2A C3A 1.367(4) . ? C2A H22A 0.9300 . ? C3A C4A 1.371(4) . ? C3A H3A 0.9300 . ? C4A C5A 1.367(4) . ? C4A H4A 0.9300 . ? C5A C6A 1.377(4) . ? C5A H5A 0.9300 . ? C6A H6A 0.9300 . ? C7A O2 1.214(4) . ? C7A N1A 1.346(4) . ? C7A N2A 1.372(4) . ? C8A N3A 1.278(4) . ? C8A C9A 1.464(4) . ? C8A H8A 0.9300 . ? C9A N4A 1.349(4) . ? C9A C10A 1.385(4) . ? C10A C11A 1.379(5) . ? C10A H10A 0.9300 . ? C11A C12A 1.363(5) . ? C11A H11A 0.9300 . ? C12A C13A 1.367(4) . ? C12A H12A 0.9300 . ? C13A N4A 1.327(4) . ? C13A H13A 0.9300 . ? N1 H1 0.8600 . ? N2 N3 1.357(3) . ? N2 H7 0.8600 . ? N1A H11N 0.8600 . ? N2A N3A 1.358(3) . ? N2A H2A 0.8600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 119.5(2) . . ? C6 C1 N1 117.4(2) . . ? C2 C1 N1 123.1(2) . . ? C1 C2 C3 119.5(3) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C4 C3 C2 121.2(3) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C3 C4 C5 118.7(3) . . ? C3 C4 H4 120.7 . . ? C5 C4 H4 120.7 . . ? C6 C5 C4 120.9(3) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C1 120.2(3) . . ? C5 C6 H6 119.9 . . ? C1 C6 H6 119.9 . . ? O1 C7 N1 125.8(2) . . ? O1 C7 N2 119.5(2) . . ? N1 C7 N2 114.7(2) . . ? N3 C8 C9 130.5(3) . . ? N3 C8 H8 114.7 . . ? C9 C8 H8 114.7 . . ? N4 C9 C10 121.9(3) . . ? N4 C9 C8 118.9(2) . . ? C10 C9 C8 119.1(3) . . ? C11 C10 C9 118.5(3) . . ? C11 C10 H10 120.7 . . ? C9 C10 H10 120.7 . . ? C12 C11 C10 119.8(3) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C11 C12 C13 118.3(3) . . ? C11 C12 H12 120.8 . . ? C13 C12 H12 120.8 . . ? N4 C13 C12 124.0(3) . . ? N4 C13 H13 118.0 . . ? C12 C13 H13 118.0 . . ? C6A C1A C2A 118.8(3) . . ? C6A C1A N1A 123.8(3) . . ? C2A C1A N1A 117.5(3) . . ? C3A C2A C1A 120.5(3) . . ? C3A C2A H22A 119.7 . . ? C1A C2A H22A 119.7 . . ? C2A C3A C4A 120.6(3) . . ? C2A C3A H3A 119.7 . . ? C4A C3A H3A 119.7 . . ? C5A C4A C3A 119.3(3) . . ? C5A C4A H4A 120.4 . . ? C3A C4A H4A 120.4 . . ? C4A C5A C6A 120.9(3) . . ? C4A C5A H5A 119.6 . . ? C6A C5A H5A 119.6 . . ? C5A C6A C1A 119.9(3) . . ? C5A C6A H6A 120.0 . . ? C1A C6A H6A 120.0 . . ? O2 C7A N1A 125.9(3) . . ? O2 C7A N2A 119.9(3) . . ? N1A C7A N2A 114.2(3) . . ? N3A C8A C9A 131.3(3) . . ? N3A C8A H8A 114.4 . . ? C9A C8A H8A 114.4 . . ? N4A C9A C10A 121.6(3) . . ? N4A C9A C8A 119.1(3) . . ? C10A C9A C8A 119.3(3) . . ? C11A C10A C9A 119.3(3) . . ? C11A C10A H10A 120.3 . . ? C9A C10A H10A 120.3 . . ? C12A C11A C10A 118.8(3) . . ? C12A C11A H11A 120.6 . . ? C10A C11A H11A 120.6 . . ? C11A C12A C13A 118.7(3) . . ? C11A C12A H12A 120.6 . . ? C13A C12A H12A 120.6 . . ? N4A C13A C12A 124.2(3) . . ? N4A C13A H13A 117.9 . . ? C12A C13A H13A 117.9 . . ? C7 N1 C1 128.7(2) . . ? C7 N1 H1 115.7 . . ? C1 N1 H1 115.7 . . ? N3 N2 C7 120.4(2) . . ? N3 N2 H7 119.8 . . ? C7 N2 H7 119.8 . . ? C8 N3 N2 118.8(2) . . ? C13 N4 C9 117.4(2) . . ? C7A N1A C1A 127.9(3) . . ? C7A N1A H11N 116.0 . . ? C1A N1A H11N 116.0 . . ? N3A N2A C7A 119.9(3) . . ? N3A N2A H2A 120.1 . . ? C7A N2A H2A 120.1 . . ? C8A N3A N2A 118.5(3) . . ? C13A N4A C9A 117.3(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 C12A H12A O2 0.93 2.58 3.368(4) 142.6 3_666 C6A H6A O2 0.93 2.27 2.873(4) 122.2 . C2 H2 O1 0.93 2.29 2.896(3) 122.1 . N1A H11N N3A 0.86 2.17 2.601(4) 110.6 . N2A H2A N4A 0.86 2.07 2.710(4) 130.3 . N2 H7 N4 0.86 2.02 2.688(3) 134.2 . N1 H1 N3 0.86 2.20 2.624(3) 110.0 . _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.182 _refine_diff_density_min -0.159 _refine_diff_density_rms 0.036 # Attachment '- crystal in acetone.cif' data_p_crystal_in_acetone _database_code_depnum_ccdc_archive 'CCDC 824334' #TrackingRef '- crystal in acetone.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C13H12N4O), C3H6O' _chemical_formula_sum 'C29 H30 N8 O3' _chemical_formula_weight 538.61 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 Pbcn _symmetry_space_group_name_Hall -p2n2ab loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 17.889(3) _cell_length_b 8.6684(9) _cell_length_c 18.288(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2835.9(6) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 2597 _cell_measurement_theta_min 3.2 _cell_measurement_theta_max 25.5 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.262 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1136 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9773 _exptl_absorpt_correction_T_max 0.9932 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 'multiwire proportional' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12064 _diffrn_reflns_av_R_equivalents 0.0381 _diffrn_reflns_av_sigmaI/netI 0.0320 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.19 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2597 _reflns_number_gt 1899 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker FRAMBO' _computing_cell_refinement 'Bruker FRAMBO' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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. The slovent acetone methyl moieties showed signs of extensive disorder, so the "isor 0.005 c14 " restraints was used to ensure the geometry of methyl fragments remained regular. ; _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^)+(0.1223P)^2^+0.9673P] 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 2597 _refine_ls_number_parameters 183 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1005 _refine_ls_R_factor_gt 0.0759 _refine_ls_wR_factor_ref 0.2268 _refine_ls_wR_factor_gt 0.2082 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.117 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.87597(16) 0.3646(3) 0.30121(14) 0.0475(7) Uani 1 1 d . . . C2 C 0.8198(2) 0.4632(4) 0.32325(18) 0.0707(10) Uani 1 1 d . . . H2 H 0.8191 0.4999 0.3710 0.085 Uiso 1 1 calc R . . C3 C 0.7652(3) 0.5075(5) 0.2752(2) 0.0865(13) Uani 1 1 d . . . H3 H 0.7278 0.5746 0.2906 0.104 Uiso 1 1 calc R . . C4 C 0.7650(2) 0.4534(4) 0.2041(2) 0.0756(10) Uani 1 1 d . . . H4 H 0.7280 0.4845 0.1715 0.091 Uiso 1 1 calc R . . C5 C 0.8192(2) 0.3547(4) 0.18249(18) 0.0703(10) Uani 1 1 d . . . H5 H 0.8187 0.3164 0.1350 0.084 Uiso 1 1 calc R . . C6 C 0.87584(18) 0.3092(3) 0.23027(16) 0.0567(8) Uani 1 1 d . . . H6 H 0.9132 0.2423 0.2146 0.068 Uiso 1 1 calc R . . C7 C 0.96082(17) 0.3958(3) 0.40581(15) 0.0504(7) Uani 1 1 d . . . C8 C 1.08727(18) 0.1290(3) 0.47907(15) 0.0520(7) Uani 1 1 d . . . H8 H 1.1034 0.1930 0.5167 0.062 Uiso 1 1 calc R . . C9 C 1.11827(17) -0.0271(3) 0.47383(15) 0.0493(7) Uani 1 1 d . . . C10 C 1.0933(2) -0.1327(4) 0.42353(17) 0.0645(9) Uani 1 1 d . . . H10 H 1.0548 -0.1073 0.3916 0.077 Uiso 1 1 calc R . . C11 C 1.1256(3) -0.2759(4) 0.4208(2) 0.0792(11) Uani 1 1 d . . . H11 H 1.1102 -0.3479 0.3863 0.095 Uiso 1 1 calc R . . C12 C 1.1807(2) -0.3111(4) 0.4698(2) 0.0782(11) Uani 1 1 d . . . H12 H 1.2031 -0.4078 0.4695 0.094 Uiso 1 1 calc R . . C13 C 1.2021(2) -0.2019(4) 0.5189(2) 0.0758(11) Uani 1 1 d . . . H13 H 1.2395 -0.2270 0.5521 0.091 Uiso 1 1 calc R . . C14 C 0.9345(6) 0.8096(10) 0.2853(5) 0.186(3) Uani 1 1 d U . . H14A H 0.9117 0.8779 0.3201 0.280 Uiso 1 1 calc R . . H14B H 0.9514 0.7182 0.3099 0.280 Uiso 1 1 calc R . . H14C H 0.8986 0.7822 0.2485 0.280 Uiso 1 1 calc R . . C15 C 1.0000 0.8891(7) 0.2500 0.100(2) Uani 1 2 d S . . N1 N 0.93265(14) 0.3137(3) 0.34928(13) 0.0520(7) Uani 1 1 d . . . H1 H 0.9507 0.2231 0.3420 0.062 Uiso 1 1 calc R . . N2 N 1.01592(17) 0.3274(3) 0.44600(14) 0.0595(7) Uani 1 1 d . . . H7 H 1.0369 0.3794 0.4804 0.071 Uiso 1 1 calc R . . N3 N 1.03897(15) 0.1800(2) 0.43380(12) 0.0493(6) Uani 1 1 d . . . N4 N 1.17216(17) -0.0595(3) 0.52215(15) 0.0687(8) Uani 1 1 d . . . O1 O 0.94030(15) 0.5273(2) 0.42197(12) 0.0669(7) Uani 1 1 d . . . O2 O 1.0000 1.0210(5) 0.2500 0.1018(14) Uani 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0502(18) 0.0414(14) 0.0508(15) 0.0044(11) -0.0034(12) -0.0035(12) C2 0.077(3) 0.072(2) 0.0627(19) -0.0154(16) -0.0144(17) 0.0242(18) C3 0.081(3) 0.085(3) 0.093(3) -0.014(2) -0.023(2) 0.033(2) C4 0.076(3) 0.077(2) 0.073(2) 0.0052(17) -0.0228(19) 0.0068(19) C5 0.079(3) 0.081(2) 0.0512(17) 0.0004(16) -0.0098(17) -0.0075(19) C6 0.059(2) 0.0594(17) 0.0519(17) -0.0033(13) 0.0037(14) -0.0019(14) C7 0.058(2) 0.0419(14) 0.0509(16) 0.0021(12) -0.0058(13) 0.0041(13) C8 0.0549(19) 0.0512(16) 0.0499(15) 0.0017(12) -0.0031(13) 0.0000(13) C9 0.0452(17) 0.0530(16) 0.0496(15) 0.0102(12) 0.0055(12) 0.0008(13) C10 0.072(2) 0.0600(18) 0.0611(18) -0.0020(15) -0.0065(16) 0.0152(16) C11 0.092(3) 0.067(2) 0.078(2) -0.0092(18) -0.005(2) 0.022(2) C12 0.078(3) 0.060(2) 0.097(3) 0.0159(19) 0.019(2) 0.0199(18) C13 0.059(2) 0.073(2) 0.095(3) 0.024(2) -0.0119(19) 0.0109(18) C14 0.197(5) 0.183(5) 0.180(5) 0.048(4) -0.035(4) -0.045(4) C15 0.133(6) 0.063(3) 0.104(4) 0.000 -0.065(4) 0.000 N1 0.0561(16) 0.0437(12) 0.0563(14) -0.0040(10) -0.0049(11) 0.0076(11) N2 0.075(2) 0.0474(13) 0.0559(14) -0.0032(11) -0.0147(13) 0.0073(12) N3 0.0538(16) 0.0458(13) 0.0484(13) 0.0032(10) 0.0014(11) 0.0038(11) N4 0.0623(19) 0.0626(17) 0.0813(18) 0.0146(14) -0.0133(14) 0.0029(13) O1 0.0911(19) 0.0447(12) 0.0648(13) -0.0056(9) -0.0241(12) 0.0110(11) O2 0.126(4) 0.068(2) 0.111(3) 0.000 -0.021(3) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.379(4) . ? C1 C6 1.383(4) . ? C1 N1 1.413(4) . ? C2 C3 1.369(5) . ? C2 H2 0.9300 . ? C3 C4 1.383(5) . ? C3 H3 0.9300 . ? C4 C5 1.353(5) . ? C4 H4 0.9300 . ? C5 C6 1.395(5) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 O1 1.233(3) . ? C7 N1 1.353(4) . ? C7 N2 1.365(4) . ? C8 N3 1.276(4) . ? C8 C9 1.465(4) . ? C8 H8 0.9300 . ? C9 N4 1.338(4) . ? C9 C10 1.373(4) . ? C10 C11 1.370(5) . ? C10 H10 0.9300 . ? C11 C12 1.366(6) . ? C11 H11 0.9300 . ? C12 C13 1.359(6) . ? C12 H12 0.9300 . ? C13 N4 1.347(4) . ? C13 H13 0.9300 . ? C14 C15 1.505(9) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 O2 1.143(6) . ? C15 C14 1.505(9) 3_755 ? N1 H1 0.8600 . ? N2 N3 1.360(3) . ? N2 H7 0.8600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 119.2(3) . . ? C2 C1 N1 122.3(3) . . ? C6 C1 N1 118.5(3) . . ? C3 C2 C1 120.4(3) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C2 C3 C4 120.7(4) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C5 C4 C3 119.1(3) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C4 C5 C6 121.1(3) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C1 C6 C5 119.4(3) . . ? C1 C6 H6 120.3 . . ? C5 C6 H6 120.3 . . ? O1 C7 N1 124.0(3) . . ? O1 C7 N2 119.2(3) . . ? N1 C7 N2 116.8(2) . . ? N3 C8 C9 122.3(3) . . ? N3 C8 H8 118.9 . . ? C9 C8 H8 118.9 . . ? N4 C9 C10 122.5(3) . . ? N4 C9 C8 115.1(3) . . ? C10 C9 C8 122.4(3) . . ? C11 C10 C9 119.4(3) . . ? C11 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? C12 C11 C10 118.9(4) . . ? C12 C11 H11 120.6 . . ? C10 C11 H11 120.6 . . ? C13 C12 C11 118.7(3) . . ? C13 C12 H12 120.6 . . ? C11 C12 H12 120.6 . . ? N4 C13 C12 123.8(3) . . ? N4 C13 H13 118.1 . . ? C12 C13 H13 118.1 . . ? C15 C14 H14A 109.5 . . ? C15 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C15 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O2 C15 C14 117.2(4) . 3_755 ? O2 C15 C14 117.2(4) . . ? C14 C15 C14 125.5(9) 3_755 . ? C7 N1 C1 125.4(2) . . ? C7 N1 H1 117.3 . . ? C1 N1 H1 117.3 . . ? N3 N2 C7 122.6(2) . . ? N3 N2 H7 118.7 . . ? C7 N2 H7 118.7 . . ? C8 N3 N2 115.1(2) . . ? C9 N4 C13 116.7(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 C2 H2 O1 0.93 2.37 2.866(4) 112.9 . N1 H1 N3 0.86 2.33 2.711(3) 106.8 . C6 H6 O2 0.93 2.55 3.363(4) 145.9 1_545 N1 H1 O2 0.86 2.58 3.345(4) 148.0 1_545 _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.770 _refine_diff_density_min -0.269 _refine_diff_density_rms 0.047 data_y _database_code_depnum_ccdc_archive 'CCDC 874338' #TrackingRef '- E-1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H12 N4 O' _chemical_formula_sum 'C13 H12 N4 O' _chemical_formula_weight 240.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.1873(3) _cell_length_b 9.2450(5) _cell_length_c 25.3594(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1216.15(11) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1431 _cell_measurement_theta_min 2.3375 _cell_measurement_theta_max 29.0363 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.312 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9656 _exptl_absorpt_correction_T_max 0.9783 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.4 (release 27-04-2006 CrysAlis171 .NET) (compiled Apr 27 2007,17:53:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Gemini S Ultra CrysAlis CCD, Oxford' _diffrn_measurement_method 'CrysAlis RED, Oxford Diffraction' _diffrn_detector_area_resol_mean 16.1903 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5181 _diffrn_reflns_av_R_equivalents 0.0489 _diffrn_reflns_av_sigmaI/netI 0.0877 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 25.98 _reflns_number_total 1419 _reflns_number_gt 809 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.31.8 ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-II (Johnson, 1976)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0276P)^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 refxyz _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1419 _refine_ls_number_parameters 211 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0732 _refine_ls_R_factor_gt 0.0338 _refine_ls_wR_factor_ref 0.0620 _refine_ls_wR_factor_gt 0.0544 _refine_ls_goodness_of_fit_ref 0.816 _refine_ls_restrained_S_all 0.816 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4077(5) 0.2554(3) 0.19816(9) 0.0304(6) Uani 1 1 d . . . C2 C 0.1998(6) 0.1627(3) 0.20304(11) 0.0390(7) Uani 1 1 d . . . C3 C 0.0531(6) 0.1674(3) 0.24851(11) 0.0439(7) Uani 1 1 d . . . C4 C 0.1080(6) 0.2641(3) 0.28855(11) 0.0428(8) Uani 1 1 d . . . C5 C 0.3152(6) 0.3552(3) 0.28336(11) 0.0413(8) Uani 1 1 d . . . C6 C 0.4629(6) 0.3521(3) 0.23838(10) 0.0368(7) Uani 1 1 d . . . C7 C 0.6005(5) 0.1593(3) 0.11492(9) 0.0335(7) Uani 1 1 d . . . C8 C 1.1211(5) 0.3333(3) 0.05345(10) 0.0348(7) Uani 1 1 d . . . C9 C 1.2837(5) 0.4622(3) 0.05609(10) 0.0309(7) Uani 1 1 d . . . C10 C 1.2743(6) 0.5625(3) 0.09700(11) 0.0440(8) Uani 1 1 d . . . C11 C 1.4365(7) 0.6794(3) 0.09588(12) 0.0502(9) Uani 1 1 d . . . C12 C 1.6083(6) 0.6941(4) 0.05510(13) 0.0460(8) Uani 1 1 d . . . C13 C 1.6071(6) 0.5922(3) 0.01580(11) 0.0445(8) Uani 1 1 d . . . H1 H 0.699(5) 0.326(3) 0.1528(9) 0.037(8) Uiso 1 1 d . . . H2 H 0.157(5) 0.098(3) 0.1748(9) 0.043(8) Uiso 1 1 d . . . H3 H -0.094(5) 0.102(3) 0.2519(9) 0.047(8) Uiso 1 1 d . . . H4 H -0.001(4) 0.263(3) 0.3223(9) 0.053(8) Uiso 1 1 d . . . H5 H 0.357(5) 0.427(3) 0.3112(9) 0.054(9) Uiso 1 1 d . . . H6 H 0.608(5) 0.415(3) 0.2343(9) 0.037(8) Uiso 1 1 d . . . H7 H 0.829(5) 0.137(3) 0.0530(10) 0.058(10) Uiso 1 1 d . . . H8 H 1.150(5) 0.270(3) 0.0241(8) 0.047(8) Uiso 1 1 d . . . H10 H 1.158(5) 0.546(3) 0.1263(9) 0.042(8) Uiso 1 1 d . . . H11 H 1.426(5) 0.756(3) 0.1232(10) 0.063(9) Uiso 1 1 d . . . H12 H 1.728(5) 0.770(3) 0.0503(10) 0.059(10) Uiso 1 1 d . . . H13 H 1.726(5) 0.599(3) -0.0152(9) 0.050(8) Uiso 1 1 d . . . N1 N 0.5723(5) 0.2579(3) 0.15391(8) 0.0360(6) Uani 1 1 d . . . N2 N 0.8007(4) 0.1898(3) 0.08109(9) 0.0374(6) Uani 1 1 d . . . N3 N 0.9425(4) 0.3137(2) 0.08734(7) 0.0335(6) Uani 1 1 d . . . N4 N 1.4475(4) 0.4772(2) 0.01521(8) 0.0369(6) Uani 1 1 d . . . O1 O 0.4702(3) 0.0502(2) 0.10857(7) 0.0430(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 C1 0.0283(15) 0.0301(15) 0.0328(13) 0.0054(14) -0.0041(14) 0.0006(17) C2 0.0389(17) 0.0382(19) 0.0400(16) -0.0004(17) -0.0054(14) -0.0024(19) C3 0.0376(17) 0.0393(19) 0.0548(18) 0.0062(18) 0.0038(17) -0.002(2) C4 0.0444(19) 0.0412(18) 0.0428(16) 0.0057(17) 0.0082(16) 0.0039(18) C5 0.0487(19) 0.0367(19) 0.0384(17) -0.0035(17) -0.0026(16) 0.0029(19) C6 0.0386(17) 0.0321(17) 0.0396(16) -0.0016(15) -0.0002(14) -0.0055(18) C7 0.0416(17) 0.0313(17) 0.0276(13) 0.0040(16) -0.0064(14) 0.0010(18) C8 0.0424(18) 0.0332(18) 0.0289(13) -0.0005(15) -0.0021(14) 0.0011(17) C9 0.0346(16) 0.0269(16) 0.0310(14) 0.0006(14) -0.0026(14) 0.0024(15) C10 0.0471(18) 0.046(2) 0.0386(16) -0.0127(18) 0.0024(16) -0.010(2) C11 0.0554(19) 0.044(2) 0.0515(18) -0.0158(19) -0.0065(18) -0.005(2) C12 0.046(2) 0.0327(19) 0.0592(18) -0.0013(18) -0.0043(18) -0.0101(19) C13 0.0439(18) 0.0450(19) 0.0446(17) 0.0060(18) -0.0009(17) -0.0056(19) N1 0.0392(14) 0.0348(14) 0.0339(12) -0.0063(12) 0.0035(12) -0.0132(16) N2 0.0493(15) 0.0328(15) 0.0300(12) -0.0033(13) 0.0033(13) -0.0094(15) N3 0.0405(12) 0.0298(14) 0.0302(11) 0.0029(11) -0.0027(12) -0.0047(14) N4 0.0386(13) 0.0349(13) 0.0374(12) 0.0016(12) 0.0011(12) -0.0013(14) O1 0.0556(13) 0.0334(11) 0.0400(10) -0.0019(11) 0.0000(10) -0.0104(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.383(3) . ? C1 C6 1.387(3) . ? C1 N1 1.410(3) . ? C2 C3 1.382(4) . ? C2 H2 0.96(2) . ? C3 C4 1.383(4) . ? C3 H3 0.98(3) . ? C4 C5 1.372(4) . ? C4 H4 1.03(2) . ? C5 C6 1.374(4) . ? C5 H5 0.99(3) . ? C6 H6 0.95(2) . ? C7 O1 1.225(3) . ? C7 N1 1.353(3) . ? C7 N2 1.376(3) . ? C8 N3 1.276(3) . ? C8 C9 1.461(3) . ? C8 H8 0.96(2) . ? C9 N4 1.348(3) . ? C9 C10 1.393(4) . ? C10 C11 1.370(4) . ? C10 H10 0.97(2) . ? C11 C12 1.372(4) . ? C11 H11 0.99(3) . ? C12 C13 1.372(4) . ? C12 H12 0.94(3) . ? C13 N4 1.347(3) . ? C13 H13 1.00(2) . ? N1 H1 0.91(2) . ? N2 N3 1.371(3) . ? N2 H7 0.88(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 119.7(2) . . ? C2 C1 N1 123.6(2) . . ? C6 C1 N1 116.7(3) . . ? C3 C2 C1 119.0(3) . . ? C3 C2 H2 121.2(15) . . ? C1 C2 H2 119.8(15) . . ? C2 C3 C4 121.3(3) . . ? C2 C3 H3 119.0(14) . . ? C4 C3 H3 119.7(14) . . ? C5 C4 C3 119.2(3) . . ? C5 C4 H4 121.1(14) . . ? C3 C4 H4 119.7(14) . . ? C4 C5 C6 120.2(3) . . ? C4 C5 H5 120.8(15) . . ? C6 C5 H5 118.9(15) . . ? C5 C6 C1 120.6(3) . . ? C5 C6 H6 121.1(14) . . ? C1 C6 H6 118.3(14) . . ? O1 C7 N1 126.3(3) . . ? O1 C7 N2 120.2(3) . . ? N1 C7 N2 113.5(3) . . ? N3 C8 C9 120.2(3) . . ? N3 C8 H8 123.5(15) . . ? C9 C8 H8 116.2(15) . . ? N4 C9 C10 121.7(3) . . ? N4 C9 C8 114.4(2) . . ? C10 C9 C8 123.9(3) . . ? C11 C10 C9 119.2(3) . . ? C11 C10 H10 121.4(15) . . ? C9 C10 H10 119.3(15) . . ? C10 C11 C12 119.5(3) . . ? C10 C11 H11 120.8(16) . . ? C12 C11 H11 119.6(16) . . ? C11 C12 C13 118.5(3) . . ? C11 C12 H12 126.7(16) . . ? C13 C12 H12 114.8(17) . . ? N4 C13 C12 123.6(3) . . ? N4 C13 H13 114.8(15) . . ? C12 C13 H13 121.6(15) . . ? C7 N1 C1 129.5(3) . . ? C7 N1 H1 111.4(15) . . ? C1 N1 H1 118.3(15) . . ? N3 N2 C7 120.3(2) . . ? N3 N2 H7 118.1(18) . . ? C7 N2 H7 121.2(18) . . ? C8 N3 N2 115.5(2) . . ? C13 N4 C9 117.4(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 C6 C1 C2 C3 -0.9(4) . . . . ? N1 C1 C2 C3 178.9(3) . . . . ? C1 C2 C3 C4 1.0(4) . . . . ? C2 C3 C4 C5 -1.2(4) . . . . ? C3 C4 C5 C6 1.3(4) . . . . ? C4 C5 C6 C1 -1.2(4) . . . . ? C2 C1 C6 C5 1.0(4) . . . . ? N1 C1 C6 C5 -178.8(3) . . . . ? N3 C8 C9 N4 -173.8(2) . . . . ? N3 C8 C9 C10 6.4(4) . . . . ? N4 C9 C10 C11 -0.3(4) . . . . ? C8 C9 C10 C11 179.6(2) . . . . ? C9 C10 C11 C12 -1.2(5) . . . . ? C10 C11 C12 C13 1.7(5) . . . . ? C11 C12 C13 N4 -0.6(4) . . . . ? O1 C7 N1 C1 5.8(4) . . . . ? N2 C7 N1 C1 -173.1(2) . . . . ? C2 C1 N1 C7 -15.3(4) . . . . ? C6 C1 N1 C7 164.5(2) . . . . ? O1 C7 N2 N3 178.3(2) . . . . ? N1 C7 N2 N3 -2.7(3) . . . . ? C9 C8 N3 N2 179.7(2) . . . . ? C7 N2 N3 C8 -178.9(2) . . . . ? C12 C13 N4 C9 -0.9(4) . . . . ? C10 C9 N4 C13 1.3(4) . . . . ? C8 C9 N4 C13 -178.5(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 N2 H7 N4 0.88(3) 2.12(3) 2.988(3) 172(3) 4_455 N1 H1 N3 0.91(2) 2.09(2) 2.608(3) 115.2(19) . _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.98 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.123 _refine_diff_density_min -0.140 _refine_diff_density_rms 0.032