# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_1 _database_code_depnum_ccdc_archive 'CCDC 855279' #TrackingRef '8343_web_deposit_cif_file_0_Gui-GeHou_1322038401.1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H26 N8 O2' _chemical_formula_weight 554.61 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.8525(19) _cell_length_b 10.375(2) _cell_length_c 13.982(3) _cell_angle_alpha 72.383(3) _cell_angle_beta 89.789(2) _cell_angle_gamma 80.764(3) _cell_volume 1343.0(4) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2003 _cell_measurement_theta_min 2.536 _cell_measurement_theta_max 26.735 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.371 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 580 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'smart APEX' _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 7088 _diffrn_reflns_av_R_equivalents 0.0168 _diffrn_reflns_av_sigmaI/netI 0.0374 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 25.50 _reflns_number_total 4900 _reflns_number_gt 3433 _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, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0755P)^2^+0.1619P] 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 4900 _refine_ls_number_parameters 381 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0788 _refine_ls_R_factor_gt 0.0546 _refine_ls_wR_factor_ref 0.1509 _refine_ls_wR_factor_gt 0.1343 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.86732(18) 0.0008(2) 0.85767(16) 0.0638(6) Uani 1 1 d . . . C1 C 0.7659(2) 0.0919(2) 0.8706(2) 0.0602(6) Uani 1 1 d . . . H1 H 0.7779 0.1750 0.8791 0.072 Uiso 1 1 calc R . . C2 C 0.8066(2) -0.1031(2) 0.84803(18) 0.0552(6) Uani 1 1 d . . . H2 H 0.8531 -0.1829 0.8378 0.066 Uiso 1 1 calc R . . C3 C 0.6702(2) -0.0749(2) 0.85537(18) 0.0554(6) Uani 1 1 d . . . H3 H 0.6063 -0.1302 0.8512 0.066 Uiso 1 1 calc R . . C4 C 0.51164(19) 0.1273(2) 0.87819(14) 0.0396(5) Uani 1 1 d . . . C5 C 0.3940(2) 0.0788(2) 0.86316(17) 0.0513(6) Uani 1 1 d . . . H5 H 0.4007 -0.0041 0.8492 0.062 Uiso 1 1 calc R . . C6 C 0.2667(2) 0.1522(2) 0.86865(17) 0.0495(5) Uani 1 1 d . . . H6 H 0.1884 0.1179 0.8581 0.059 Uiso 1 1 calc R . . C7 C 0.25167(19) 0.2760(2) 0.88947(14) 0.0397(5) Uani 1 1 d . . . C8 C 0.3717(2) 0.3236(2) 0.90371(17) 0.0513(6) Uani 1 1 d . . . H8 H 0.3652 0.4070 0.9168 0.062 Uiso 1 1 calc R . . C9 C 0.4997(2) 0.2508(2) 0.89894(17) 0.0515(6) Uani 1 1 d . . . H9 H 0.5783 0.2846 0.9097 0.062 Uiso 1 1 calc R . . C10 C 0.11361(19) 0.3532(2) 0.89383(14) 0.0400(5) Uani 1 1 d . . . C11 C 0.0003(2) 0.2900(2) 0.92246(17) 0.0499(5) Uani 1 1 d . . . H11 H 0.0130 0.1947 0.9410 0.060 Uiso 1 1 calc R . . C12 C -0.1367(2) 0.4924(2) 0.90036(17) 0.0534(6) Uani 1 1 d . . . H12 H -0.2240 0.5409 0.9029 0.064 Uiso 1 1 calc R . . C13 C 0.0865(2) 0.4951(2) 0.86939(15) 0.0466(5) Uani 1 1 d . . . H13 H 0.1591 0.5431 0.8498 0.056 Uiso 1 1 calc R . . C14 C -0.1722(2) 0.5691(2) 0.65470(17) 0.0535(6) Uani 1 1 d . . . H14 H -0.1775 0.4761 0.6738 0.064 Uiso 1 1 calc R . . C15 C -0.2258(2) 0.7845(3) 0.6223(2) 0.0643(7) Uani 1 1 d . . . H15 H -0.2768 0.8710 0.6142 0.077 Uiso 1 1 calc R . . C16 C -0.0924(2) 0.7603(2) 0.6033(2) 0.0640(7) Uani 1 1 d . . . H16 H -0.0349 0.8251 0.5807 0.077 Uiso 1 1 calc R . . C17 C 0.07529(19) 0.5441(2) 0.61971(15) 0.0426(5) Uani 1 1 d . . . C18 C 0.1911(2) 0.6027(2) 0.62091(18) 0.0558(6) Uani 1 1 d . . . H18 H 0.1824 0.6921 0.6237 0.067 Uiso 1 1 calc R . . C19 C 0.3186(2) 0.5298(2) 0.61806(18) 0.0548(6) Uani 1 1 d . . . H19 H 0.3957 0.5709 0.6185 0.066 Uiso 1 1 calc R . . C20 C 0.33613(19) 0.3957(2) 0.61448(15) 0.0427(5) Uani 1 1 d . . . C21 C 0.2183(2) 0.3380(2) 0.61506(16) 0.0482(5) Uani 1 1 d . . . H21 H 0.2268 0.2478 0.6143 0.058 Uiso 1 1 calc R . . C22 C 0.0897(2) 0.4109(2) 0.61677(16) 0.0481(5) Uani 1 1 d . . . H22 H 0.0122 0.3705 0.6159 0.058 Uiso 1 1 calc R . . C23 C 0.4750(2) 0.3182(2) 0.61241(15) 0.0452(5) Uani 1 1 d . . . C24 C 0.5930(2) 0.3535(3) 0.64364(19) 0.0624(6) Uani 1 1 d . . . H24 H 0.5831 0.4297 0.6664 0.075 Uiso 1 1 calc R . . C25 C 0.7271(2) 0.1784(3) 0.61034(19) 0.0655(7) Uani 1 1 d . . . H25 H 0.8149 0.1299 0.6097 0.079 Uiso 1 1 calc R . . C26 C 0.4998(2) 0.2043(2) 0.57922(17) 0.0563(6) Uani 1 1 d . . . H26 H 0.4248 0.1761 0.5560 0.068 Uiso 1 1 calc R . . C27 C 0.4152(2) 0.7379(2) 0.77637(18) 0.0496(5) Uani 1 1 d . . . C28 C 0.3193(2) 0.7417(2) 0.84783(18) 0.0514(5) Uani 1 1 d . . . H28 H 0.3355 0.6790 0.9118 0.062 Uiso 1 1 calc R . . C29 C 0.1994(2) 0.8372(2) 0.82599(18) 0.0518(6) Uani 1 1 d . . . H29 H 0.1355 0.8376 0.8751 0.062 Uiso 1 1 calc R . . C30 C 0.1740(2) 0.9314(2) 0.73206(18) 0.0508(5) Uani 1 1 d . . . C31 C 0.2686(2) 0.9276(2) 0.66035(17) 0.0513(5) Uani 1 1 d . . . H31 H 0.2515 0.9899 0.5962 0.062 Uiso 1 1 calc R . . C32 C 0.3886(2) 0.8331(2) 0.68156(18) 0.0523(6) Uani 1 1 d . . . H32 H 0.4520 0.8331 0.6321 0.063 Uiso 1 1 calc R . . N2 N 0.64298(16) 0.05168(17) 0.87031(12) 0.0431(4) Uani 1 1 d . . . N3 N -0.12579(17) 0.3570(2) 0.92507(15) 0.0560(5) Uani 1 1 d . . . N4 N -0.03727(18) 0.56622(18) 0.87245(14) 0.0537(5) Uani 1 1 d . . . N5 N -0.27598(18) 0.6655(2) 0.65487(15) 0.0615(5) Uani 1 1 d . . . N6 N -0.05726(16) 0.62044(18) 0.62377(13) 0.0466(4) Uani 1 1 d . . . N7 N 0.71848(19) 0.2864(2) 0.64336(18) 0.0711(6) Uani 1 1 d . . . N8 N 0.6242(2) 0.1325(2) 0.57832(16) 0.0636(5) Uani 1 1 d . . . O1 O 0.53072(15) 0.64041(17) 0.80242(14) 0.0694(5) Uani 1 1 d . . . H1A H 0.5835 0.6532 0.7563 0.104 Uiso 1 1 calc R . . O2 O 0.05909(15) 1.03027(17) 0.70661(14) 0.0697(5) Uani 1 1 d . . . H2A H 0.0073 1.0188 0.7534 0.105 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0411(10) 0.0573(13) 0.0946(16) -0.0300(11) 0.0062(10) 0.0002(9) C1 0.0397(12) 0.0534(14) 0.0941(19) -0.0330(13) 0.0054(11) -0.0061(11) C2 0.0501(13) 0.0463(13) 0.0703(16) -0.0247(12) 0.0067(11) 0.0020(11) C3 0.0470(12) 0.0486(13) 0.0786(16) -0.0325(12) 0.0072(11) -0.0058(10) C4 0.0361(10) 0.0391(11) 0.0437(11) -0.0147(9) 0.0053(8) -0.0027(9) C5 0.0449(12) 0.0419(12) 0.0770(16) -0.0329(11) 0.0016(10) -0.0072(10) C6 0.0353(11) 0.0487(13) 0.0726(15) -0.0291(12) 0.0019(10) -0.0099(10) C7 0.0398(11) 0.0396(11) 0.0425(11) -0.0168(9) 0.0045(8) -0.0065(9) C8 0.0458(12) 0.0469(13) 0.0733(15) -0.0350(12) 0.0104(10) -0.0109(10) C9 0.0368(11) 0.0562(14) 0.0753(16) -0.0378(12) 0.0077(10) -0.0130(10) C10 0.0379(10) 0.0432(12) 0.0425(11) -0.0191(9) 0.0032(8) -0.0058(9) C11 0.0402(11) 0.0437(12) 0.0658(14) -0.0181(11) 0.0042(10) -0.0051(10) C12 0.0424(12) 0.0610(16) 0.0588(14) -0.0282(12) -0.0011(10) 0.0051(11) C13 0.0466(12) 0.0436(12) 0.0541(13) -0.0213(10) 0.0056(10) -0.0083(10) C14 0.0408(12) 0.0580(14) 0.0655(15) -0.0266(12) 0.0067(10) -0.0043(11) C15 0.0544(14) 0.0572(15) 0.0832(18) -0.0326(14) -0.0008(12) 0.0069(13) C16 0.0559(14) 0.0480(14) 0.0899(19) -0.0269(13) 0.0076(13) -0.0030(12) C17 0.0403(11) 0.0455(12) 0.0438(12) -0.0181(10) 0.0051(9) -0.0039(9) C18 0.0496(13) 0.0419(13) 0.0826(17) -0.0277(12) 0.0132(11) -0.0101(11) C19 0.0435(12) 0.0492(13) 0.0776(16) -0.0246(12) 0.0111(11) -0.0145(11) C20 0.0410(11) 0.0458(12) 0.0416(11) -0.0140(9) 0.0059(9) -0.0066(9) C21 0.0459(12) 0.0428(12) 0.0606(14) -0.0243(11) 0.0025(10) -0.0045(10) C22 0.0409(11) 0.0500(13) 0.0602(14) -0.0248(11) 0.0050(10) -0.0118(10) C23 0.0426(11) 0.0459(12) 0.0439(12) -0.0099(10) 0.0065(9) -0.0055(10) C24 0.0470(13) 0.0583(15) 0.0854(18) -0.0293(13) 0.0003(12) -0.0045(12) C25 0.0465(14) 0.0656(17) 0.0742(17) -0.0145(14) 0.0053(12) 0.0068(12) C26 0.0474(12) 0.0572(14) 0.0664(15) -0.0254(12) 0.0032(11) -0.0023(11) C27 0.0378(11) 0.0481(13) 0.0715(16) -0.0300(12) 0.0059(10) -0.0093(10) C28 0.0471(12) 0.0475(13) 0.0634(15) -0.0198(11) 0.0078(10) -0.0133(10) C29 0.0426(12) 0.0532(14) 0.0665(15) -0.0253(12) 0.0176(10) -0.0148(11) C30 0.0374(11) 0.0481(13) 0.0739(16) -0.0272(12) 0.0088(10) -0.0110(10) C31 0.0471(12) 0.0514(13) 0.0588(14) -0.0196(11) 0.0057(10) -0.0134(11) C32 0.0420(12) 0.0605(15) 0.0638(15) -0.0317(13) 0.0140(10) -0.0114(11) N2 0.0367(9) 0.0426(10) 0.0535(11) -0.0205(8) 0.0041(7) -0.0050(8) N3 0.0398(10) 0.0558(12) 0.0737(13) -0.0236(10) 0.0070(9) -0.0045(9) N4 0.0525(11) 0.0456(11) 0.0638(12) -0.0236(9) 0.0017(9) 0.0023(9) N5 0.0435(10) 0.0687(14) 0.0757(14) -0.0327(11) 0.0056(9) 0.0012(10) N6 0.0396(9) 0.0501(11) 0.0538(11) -0.0235(9) 0.0044(8) -0.0036(8) N7 0.0451(11) 0.0691(14) 0.0986(17) -0.0294(13) -0.0017(11) -0.0006(10) N8 0.0538(12) 0.0605(13) 0.0765(14) -0.0285(11) 0.0038(10) 0.0056(10) O1 0.0471(9) 0.0667(11) 0.0897(13) -0.0246(10) 0.0083(8) 0.0054(8) O2 0.0428(9) 0.0662(11) 0.0934(13) -0.0207(10) 0.0087(8) 0.0028(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.313(3) . ? N1 C2 1.354(3) . ? C1 N2 1.344(3) . ? C1 H1 0.9300 . ? C2 C3 1.339(3) . ? C2 H2 0.9300 . ? C3 N2 1.376(3) . ? C3 H3 0.9300 . ? C4 C5 1.376(3) . ? C4 C9 1.384(3) . ? C4 N2 1.424(2) . ? C5 C6 1.374(3) . ? C5 H5 0.9300 . ? C6 C7 1.386(3) . ? C6 H6 0.9300 . ? C7 C8 1.389(3) . ? C7 C10 1.474(2) . ? C8 C9 1.375(3) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.382(3) . ? C10 C13 1.388(3) . ? C11 N3 1.329(2) . ? C11 H11 0.9300 . ? C12 N4 1.325(3) . ? C12 N3 1.327(3) . ? C12 H12 0.9300 . ? C13 N4 1.328(2) . ? C13 H13 0.9300 . ? C14 N5 1.311(3) . ? C14 N6 1.343(3) . ? C14 H14 0.9300 . ? C15 C16 1.339(3) . ? C15 N5 1.352(3) . ? C15 H15 0.9300 . ? C16 N6 1.377(3) . ? C16 H16 0.9300 . ? C17 C18 1.379(3) . ? C17 C22 1.380(3) . ? C17 N6 1.425(2) . ? C18 C19 1.365(3) . ? C18 H18 0.9300 . ? C19 C20 1.390(3) . ? C19 H19 0.9300 . ? C20 C21 1.387(3) . ? C20 C23 1.477(3) . ? C21 C22 1.372(3) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 C26 1.382(3) . ? C23 C24 1.383(3) . ? C24 N7 1.318(3) . ? C24 H24 0.9300 . ? C25 N8 1.320(3) . ? C25 N7 1.326(3) . ? C25 H25 0.9300 . ? C26 N8 1.330(3) . ? C26 H26 0.9300 . ? C27 O1 1.365(2) . ? C27 C28 1.377(3) . ? C27 C32 1.388(3) . ? C28 C29 1.384(3) . ? C28 H28 0.9300 . ? C29 C30 1.375(3) . ? C29 H29 0.9300 . ? C30 O2 1.367(2) . ? C30 C31 1.371(3) . ? C31 C32 1.379(3) . ? C31 H31 0.9300 . ? C32 H32 0.9300 . ? O1 H1A 0.8200 . ? O2 H2A 0.8200 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C2 105.06(18) . . ? N1 C1 N2 112.40(19) . . ? N1 C1 H1 123.8 . . ? N2 C1 H1 123.8 . . ? C3 C2 N1 110.46(19) . . ? C3 C2 H2 124.8 . . ? N1 C2 H2 124.8 . . ? C2 C3 N2 106.65(19) . . ? C2 C3 H3 126.7 . . ? N2 C3 H3 126.7 . . ? C5 C4 C9 119.05(17) . . ? C5 C4 N2 119.79(17) . . ? C9 C4 N2 121.15(17) . . ? C6 C5 C4 120.30(18) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C7 121.86(18) . . ? C5 C6 H6 119.1 . . ? C7 C6 H6 119.1 . . ? C6 C7 C8 116.90(18) . . ? C6 C7 C10 120.59(17) . . ? C8 C7 C10 122.50(17) . . ? C9 C8 C7 121.82(18) . . ? C9 C8 H8 119.1 . . ? C7 C8 H8 119.1 . . ? C8 C9 C4 120.06(18) . . ? C8 C9 H9 120.0 . . ? C4 C9 H9 120.0 . . ? C11 C10 C13 114.40(18) . . ? C11 C10 C7 122.70(18) . . ? C13 C10 C7 122.90(18) . . ? N3 C11 C10 124.0(2) . . ? N3 C11 H11 118.0 . . ? C10 C11 H11 118.0 . . ? N4 C12 N3 127.28(19) . . ? N4 C12 H12 116.4 . . ? N3 C12 H12 116.4 . . ? N4 C13 C10 123.70(19) . . ? N4 C13 H13 118.1 . . ? C10 C13 H13 118.1 . . ? N5 C14 N6 112.0(2) . . ? N5 C14 H14 124.0 . . ? N6 C14 H14 124.0 . . ? C16 C15 N5 110.5(2) . . ? C16 C15 H15 124.7 . . ? N5 C15 H15 124.7 . . ? C15 C16 N6 106.4(2) . . ? C15 C16 H16 126.8 . . ? N6 C16 H16 126.8 . . ? C18 C17 C22 119.37(19) . . ? C18 C17 N6 119.79(18) . . ? C22 C17 N6 120.82(18) . . ? C19 C18 C17 120.1(2) . . ? C19 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? C18 C19 C20 121.73(19) . . ? C18 C19 H19 119.1 . . ? C20 C19 H19 119.1 . . ? C21 C20 C19 117.15(18) . . ? C21 C20 C23 122.00(18) . . ? C19 C20 C23 120.85(18) . . ? C22 C21 C20 121.59(19) . . ? C22 C21 H21 119.2 . . ? C20 C21 H21 119.2 . . ? C21 C22 C17 120.01(19) . . ? C21 C22 H22 120.0 . . ? C17 C22 H22 120.0 . . ? C26 C23 C24 113.6(2) . . ? C26 C23 C20 123.54(19) . . ? C24 C23 C20 122.82(19) . . ? N7 C24 C23 124.5(2) . . ? N7 C24 H24 117.7 . . ? C23 C24 H24 117.7 . . ? N8 C25 N7 126.9(2) . . ? N8 C25 H25 116.6 . . ? N7 C25 H25 116.6 . . ? N8 C26 C23 124.1(2) . . ? N8 C26 H26 117.9 . . ? C23 C26 H26 117.9 . . ? O1 C27 C28 118.2(2) . . ? O1 C27 C32 123.57(19) . . ? C28 C27 C32 118.2(2) . . ? C27 C28 C29 121.1(2) . . ? C27 C28 H28 119.4 . . ? C29 C28 H28 119.4 . . ? C30 C29 C28 120.4(2) . . ? C30 C29 H29 119.8 . . ? C28 C29 H29 119.8 . . ? O2 C30 C31 118.1(2) . . ? O2 C30 C29 123.12(19) . . ? C31 C30 C29 118.8(2) . . ? C30 C31 C32 121.2(2) . . ? C30 C31 H31 119.4 . . ? C32 C31 H31 119.4 . . ? C31 C32 C27 120.3(2) . . ? C31 C32 H32 119.8 . . ? C27 C32 H32 119.8 . . ? C1 N2 C3 105.42(17) . . ? C1 N2 C4 127.24(17) . . ? C3 N2 C4 127.26(17) . . ? C12 N3 C11 115.18(19) . . ? C12 N4 C13 115.43(18) . . ? C14 N5 C15 105.34(19) . . ? C14 N6 C16 105.75(18) . . ? C14 N6 C17 126.63(18) . . ? C16 N6 C17 127.50(19) . . ? C24 N7 C25 115.4(2) . . ? C25 N8 C26 115.4(2) . . ? C27 O1 H1A 109.5 . . ? C30 O2 H2A 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 N1 C1 N2 0.3(3) . . . . ? C1 N1 C2 C3 -0.1(3) . . . . ? N1 C2 C3 N2 0.0(3) . . . . ? C9 C4 C5 C6 0.1(3) . . . . ? N2 C4 C5 C6 -178.73(19) . . . . ? C4 C5 C6 C7 -0.2(3) . . . . ? C5 C6 C7 C8 0.6(3) . . . . ? C5 C6 C7 C10 179.4(2) . . . . ? C6 C7 C8 C9 -0.9(3) . . . . ? C10 C7 C8 C9 -179.7(2) . . . . ? C7 C8 C9 C4 0.9(3) . . . . ? C5 C4 C9 C8 -0.4(3) . . . . ? N2 C4 C9 C8 178.39(19) . . . . ? C6 C7 C10 C11 29.7(3) . . . . ? C8 C7 C10 C11 -151.6(2) . . . . ? C6 C7 C10 C13 -150.2(2) . . . . ? C8 C7 C10 C13 28.5(3) . . . . ? C13 C10 C11 N3 1.3(3) . . . . ? C7 C10 C11 N3 -178.55(19) . . . . ? C11 C10 C13 N4 -0.2(3) . . . . ? C7 C10 C13 N4 179.68(18) . . . . ? N5 C15 C16 N6 0.6(3) . . . . ? C22 C17 C18 C19 0.7(3) . . . . ? N6 C17 C18 C19 179.3(2) . . . . ? C17 C18 C19 C20 -0.4(4) . . . . ? C18 C19 C20 C21 -0.7(3) . . . . ? C18 C19 C20 C23 -179.4(2) . . . . ? C19 C20 C21 C22 1.5(3) . . . . ? C23 C20 C21 C22 -179.86(19) . . . . ? C20 C21 C22 C17 -1.1(3) . . . . ? C18 C17 C22 C21 0.0(3) . . . . ? N6 C17 C22 C21 -178.60(18) . . . . ? C21 C20 C23 C26 21.5(3) . . . . ? C19 C20 C23 C26 -159.9(2) . . . . ? C21 C20 C23 C24 -158.6(2) . . . . ? C19 C20 C23 C24 20.1(3) . . . . ? C26 C23 C24 N7 -0.4(4) . . . . ? C20 C23 C24 N7 179.6(2) . . . . ? C24 C23 C26 N8 1.1(3) . . . . ? C20 C23 C26 N8 -179.0(2) . . . . ? O1 C27 C28 C29 -179.39(19) . . . . ? C32 C27 C28 C29 0.2(3) . . . . ? C27 C28 C29 C30 -0.5(3) . . . . ? C28 C29 C30 O2 -178.40(18) . . . . ? C28 C29 C30 C31 0.9(3) . . . . ? O2 C30 C31 C32 178.23(19) . . . . ? C29 C30 C31 C32 -1.1(3) . . . . ? C30 C31 C32 C27 0.9(3) . . . . ? O1 C27 C32 C31 179.18(18) . . . . ? C28 C27 C32 C31 -0.4(3) . . . . ? N1 C1 N2 C3 -0.3(3) . . . . ? N1 C1 N2 C4 -177.19(19) . . . . ? C2 C3 N2 C1 0.2(3) . . . . ? C2 C3 N2 C4 177.09(19) . . . . ? C5 C4 N2 C1 171.3(2) . . . . ? C9 C4 N2 C1 -7.5(3) . . . . ? C5 C4 N2 C3 -4.9(3) . . . . ? C9 C4 N2 C3 176.3(2) . . . . ? N4 C12 N3 C11 1.1(3) . . . . ? C10 C11 N3 C12 -1.7(3) . . . . ? N3 C12 N4 C13 -0.1(3) . . . . ? C10 C13 N4 C12 -0.4(3) . . . . ? N6 C14 N5 C15 0.2(3) . . . . ? C16 C15 N5 C14 -0.5(3) . . . . ? N5 C14 N6 C16 0.2(3) . . . . ? N5 C14 N6 C17 176.43(18) . . . . ? C15 C16 N6 C14 -0.5(3) . . . . ? C15 C16 N6 C17 -176.67(19) . . . . ? C18 C17 N6 C14 -157.2(2) . . . . ? C22 C17 N6 C14 21.3(3) . . . . ? C18 C17 N6 C16 18.2(3) . . . . ? C22 C17 N6 C16 -163.2(2) . . . . ? C23 C24 N7 C25 -0.1(4) . . . . ? N8 C25 N7 C24 0.0(4) . . . . ? N7 C25 N8 C26 0.5(4) . . . . ? C23 C26 N8 C25 -1.1(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1A N5 0.82 1.97 2.785(3) 173.6 1_655 O2 H2A N1 0.82 1.99 2.809(3) 174.6 1_465 _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.186 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.046 data_2 _database_code_depnum_ccdc_archive 'CCDC 855280' #TrackingRef 'web_deposit_cif_file_1_Gui-GeHou_1322038401.2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H16 N4 O2' _chemical_formula_weight 332.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 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 7.599(2) _cell_length_b 9.335(3) _cell_length_c 23.306(7) _cell_angle_alpha 90.00 _cell_angle_beta 97.817(5) _cell_angle_gamma 90.00 _cell_volume 1637.9(8) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 764 _cell_measurement_theta_min 2.353 _cell_measurement_theta_max 19.520 _exptl_crystal_description bar _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.348 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'smart APEX' _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 8437 _diffrn_reflns_av_R_equivalents 0.0632 _diffrn_reflns_av_sigmaI/netI 0.0869 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 25.49 _reflns_number_total 3058 _reflns_number_gt 1901 _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, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0481P)^2^+0.2927P] 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 3058 _refine_ls_number_parameters 228 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1358 _refine_ls_R_factor_gt 0.0790 _refine_ls_wR_factor_ref 0.1699 _refine_ls_wR_factor_gt 0.1463 _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_restrained_S_all 1.106 _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 0.1819(5) 1.3530(4) 1.03027(15) 0.0522(9) Uani 1 1 d . . . H1 H 0.1531 1.3804 0.9918 0.063 Uiso 1 1 calc R . . C2 C 0.2268(6) 1.3571(5) 1.12186(17) 0.0725(12) Uani 1 1 d . . . H2 H 0.2346 1.3897 1.1598 0.087 Uiso 1 1 calc R . . C3 C 0.2625(5) 1.2218(5) 1.10696(15) 0.0676(11) Uani 1 1 d . . . H3 H 0.2995 1.1461 1.1317 0.081 Uiso 1 1 calc R . . C4 C 0.2461(4) 1.0963(3) 1.01147(13) 0.0449(8) Uani 1 1 d . . . C5 C 0.2973(4) 1.1110(3) 0.95736(13) 0.0466(8) Uani 1 1 d . . . H5 H 0.3248 1.2007 0.9437 0.056 Uiso 1 1 calc R . . C6 C 0.3072(4) 0.9906(3) 0.92378(14) 0.0467(9) Uani 1 1 d . . . H6 H 0.3383 1.0002 0.8867 0.056 Uiso 1 1 calc R . . C7 C 0.2720(4) 0.8556(3) 0.94399(14) 0.0443(8) Uani 1 1 d . . . C8 C 0.2220(4) 0.8446(4) 0.99899(15) 0.0526(9) Uani 1 1 d . . . H8 H 0.1982 0.7550 1.0135 0.063 Uiso 1 1 calc R . . C9 C 0.2075(5) 0.9636(4) 1.03191(14) 0.0524(9) Uani 1 1 d . . . H9 H 0.1713 0.9548 1.0683 0.063 Uiso 1 1 calc R . . C10 C 0.2844(4) 0.7255(3) 0.90860(14) 0.0464(9) Uani 1 1 d . . . C11 C 0.2287(5) 0.7192(4) 0.85044(16) 0.0582(10) Uani 1 1 d . . . H11 H 0.1830 0.8022 0.8320 0.070 Uiso 1 1 calc R . . C12 C 0.3034(5) 0.4867(4) 0.84728(18) 0.0618(10) Uani 1 1 d . . . H12 H 0.3088 0.4034 0.8257 0.074 Uiso 1 1 calc R . . C13 C 0.3543(5) 0.5985(4) 0.93267(16) 0.0563(10) Uani 1 1 d . . . H13 H 0.3973 0.5978 0.9720 0.068 Uiso 1 1 calc R . . C14 C 0.8684(5) 0.2342(4) 0.84679(14) 0.0515(9) Uani 1 1 d . . . C15 C 0.6856(5) 0.2403(3) 0.83904(13) 0.0486(9) Uani 1 1 d . . . H15 H 0.6277 0.3073 0.8594 0.058 Uiso 1 1 calc R . . C16 C 0.5879(5) 0.1469(4) 0.80109(13) 0.0492(9) Uani 1 1 d . . . C17 C 0.6733(5) 0.0450(4) 0.77162(14) 0.0586(10) Uani 1 1 d . . . H17 H 0.6085 -0.0200 0.7470 0.070 Uiso 1 1 calc R . . C18 C 0.8572(6) 0.0420(4) 0.77967(15) 0.0673(11) Uani 1 1 d . . . H18 H 0.9155 -0.0250 0.7595 0.081 Uiso 1 1 calc R . . C19 C 0.9554(5) 0.1350(4) 0.81650(15) 0.0640(11) Uani 1 1 d . . . H19 H 1.0788 0.1317 0.8211 0.077 Uiso 1 1 calc R . . N1 N 0.1779(4) 1.4396(3) 1.07437(13) 0.0642(9) Uani 1 1 d . . . N2 N 0.2326(4) 1.2194(3) 1.04732(11) 0.0485(7) Uani 1 1 d . . . N3 N 0.3637(4) 0.4778(3) 0.90320(14) 0.0623(9) Uani 1 1 d . . . N4 N 0.2358(4) 0.6016(3) 0.81845(13) 0.0623(9) Uani 1 1 d . . . O1 O 0.9707(3) 0.3210(3) 0.88440(11) 0.0706(8) Uani 1 1 d . . . H1A H 0.9090 0.3849 0.8953 0.106 Uiso 1 1 calc R . . O2 O 0.4071(3) 0.1580(3) 0.79463(10) 0.0641(7) Uani 1 1 d . . . H2A H 0.3652 0.1263 0.7629 0.096 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.052(2) 0.053(2) 0.050(2) 0.0011(18) -0.0005(17) -0.0068(19) C2 0.078(3) 0.089(3) 0.052(3) -0.010(2) 0.013(2) -0.008(3) C3 0.068(3) 0.092(3) 0.042(2) 0.011(2) 0.0023(18) -0.003(2) C4 0.037(2) 0.056(2) 0.0400(18) 0.0089(16) -0.0024(15) -0.0042(17) C5 0.050(2) 0.0432(19) 0.045(2) 0.0121(16) 0.0040(16) -0.0041(17) C6 0.047(2) 0.053(2) 0.0385(18) 0.0115(16) 0.0026(15) 0.0006(17) C7 0.0339(19) 0.050(2) 0.047(2) 0.0122(16) -0.0027(15) 0.0000(16) C8 0.046(2) 0.049(2) 0.062(2) 0.0182(18) 0.0056(18) -0.0050(18) C9 0.051(2) 0.060(2) 0.047(2) 0.0125(18) 0.0094(17) -0.0028(19) C10 0.036(2) 0.049(2) 0.052(2) 0.0117(17) -0.0026(16) -0.0036(17) C11 0.055(3) 0.050(2) 0.067(3) 0.0055(19) 0.0009(19) 0.0083(19) C12 0.051(3) 0.056(2) 0.078(3) -0.002(2) 0.008(2) -0.001(2) C13 0.051(2) 0.048(2) 0.066(2) 0.0112(19) -0.0047(18) -0.0059(19) C14 0.049(2) 0.062(2) 0.042(2) 0.0088(17) 0.0022(17) 0.004(2) C15 0.046(2) 0.060(2) 0.0406(19) 0.0068(16) 0.0072(16) 0.0073(19) C16 0.049(2) 0.061(2) 0.0380(19) 0.0082(17) 0.0064(16) 0.005(2) C17 0.068(3) 0.065(2) 0.042(2) 0.0007(17) 0.0037(19) 0.006(2) C18 0.071(3) 0.081(3) 0.051(2) 0.004(2) 0.011(2) 0.027(2) C19 0.044(2) 0.091(3) 0.058(2) 0.010(2) 0.0111(19) 0.019(2) N1 0.067(2) 0.068(2) 0.057(2) -0.0070(18) 0.0054(16) -0.0078(18) N2 0.0470(19) 0.0577(19) 0.0400(16) 0.0033(14) 0.0032(13) -0.0074(15) N3 0.059(2) 0.0475(19) 0.077(2) 0.0084(16) -0.0022(17) 0.0001(16) N4 0.061(2) 0.0546(19) 0.069(2) 0.0043(17) -0.0001(16) 0.0045(17) O1 0.0484(17) 0.085(2) 0.0752(18) -0.0048(15) -0.0043(14) 0.0005(14) O2 0.0443(16) 0.092(2) 0.0565(16) -0.0106(14) 0.0066(12) -0.0015(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 N1 1.311(4) . ? C1 N2 1.349(4) . ? C1 H1 0.9300 . ? C2 C3 1.347(5) . ? C2 N1 1.358(4) . ? C2 H2 0.9300 . ? C3 N2 1.378(4) . ? C3 H3 0.9300 . ? C4 C9 1.374(4) . ? C4 C5 1.376(4) . ? C4 N2 1.433(4) . ? C5 C6 1.377(4) . ? C5 H5 0.9300 . ? C6 C7 1.384(4) . ? C6 H6 0.9300 . ? C7 C8 1.389(4) . ? C7 C10 1.478(4) . ? C8 C9 1.362(4) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.365(4) . ? C10 C13 1.386(4) . ? C11 N4 1.332(4) . ? C11 H11 0.9300 . ? C12 N3 1.324(4) . ? C12 N4 1.331(4) . ? C12 H12 0.9300 . ? C13 N3 1.327(4) . ? C13 H13 0.9300 . ? C14 O1 1.358(4) . ? C14 C15 1.378(5) . ? C14 C19 1.385(5) . ? C15 C16 1.384(4) . ? C15 H15 0.9300 . ? C16 O2 1.365(4) . ? C16 C17 1.385(4) . ? C17 C18 1.385(5) . ? C17 H17 0.9300 . ? C18 C19 1.368(5) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? O1 H1A 0.8200 . ? O2 H2A 0.8200 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 N2 112.0(3) . . ? N1 C1 H1 124.0 . . ? N2 C1 H1 124.0 . . ? C3 C2 N1 111.4(3) . . ? C3 C2 H2 124.3 . . ? N1 C2 H2 124.3 . . ? C2 C3 N2 105.3(3) . . ? C2 C3 H3 127.4 . . ? N2 C3 H3 127.4 . . ? C9 C4 C5 120.5(3) . . ? C9 C4 N2 119.1(3) . . ? C5 C4 N2 120.4(3) . . ? C4 C5 C6 118.9(3) . . ? C4 C5 H5 120.5 . . ? C6 C5 H5 120.5 . . ? C5 C6 C7 121.4(3) . . ? C5 C6 H6 119.3 . . ? C7 C6 H6 119.3 . . ? C6 C7 C8 118.1(3) . . ? C6 C7 C10 121.9(3) . . ? C8 C7 C10 120.0(3) . . ? C9 C8 C7 120.9(3) . . ? C9 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C8 C9 C4 120.2(3) . . ? C8 C9 H9 119.9 . . ? C4 C9 H9 119.9 . . ? C11 C10 C13 114.5(3) . . ? C11 C10 C7 123.7(3) . . ? C13 C10 C7 121.8(3) . . ? N4 C11 C10 124.1(3) . . ? N4 C11 H11 118.0 . . ? C10 C11 H11 118.0 . . ? N3 C12 N4 127.3(3) . . ? N3 C12 H12 116.4 . . ? N4 C12 H12 116.4 . . ? N3 C13 C10 124.2(3) . . ? N3 C13 H13 117.9 . . ? C10 C13 H13 117.9 . . ? O1 C14 C15 122.6(3) . . ? O1 C14 C19 117.2(3) . . ? C15 C14 C19 120.2(3) . . ? C14 C15 C16 120.1(3) . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? O2 C16 C15 117.8(3) . . ? O2 C16 C17 122.0(3) . . ? C15 C16 C17 120.2(3) . . ? C18 C17 C16 118.6(3) . . ? C18 C17 H17 120.7 . . ? C16 C17 H17 120.7 . . ? C19 C18 C17 121.7(4) . . ? C19 C18 H18 119.1 . . ? C17 C18 H18 119.1 . . ? C18 C19 C14 119.1(4) . . ? C18 C19 H19 120.4 . . ? C14 C19 H19 120.4 . . ? C1 N1 C2 104.8(3) . . ? C1 N2 C3 106.5(3) . . ? C1 N2 C4 127.6(3) . . ? C3 N2 C4 125.9(3) . . ? C12 N3 C13 114.8(3) . . ? C12 N4 C11 115.1(3) . . ? C14 O1 H1A 109.5 . . ? C16 O2 H2A 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C2 C3 N2 -0.7(5) . . . . ? C9 C4 C5 C6 0.8(5) . . . . ? N2 C4 C5 C6 -179.4(3) . . . . ? C4 C5 C6 C7 -1.9(5) . . . . ? C5 C6 C7 C8 1.4(5) . . . . ? C5 C6 C7 C10 -179.2(3) . . . . ? C6 C7 C8 C9 0.3(5) . . . . ? C10 C7 C8 C9 -179.1(3) . . . . ? C7 C8 C9 C4 -1.4(5) . . . . ? C5 C4 C9 C8 0.9(5) . . . . ? N2 C4 C9 C8 -179.0(3) . . . . ? C6 C7 C10 C11 -39.7(5) . . . . ? C8 C7 C10 C11 139.6(4) . . . . ? C6 C7 C10 C13 140.5(3) . . . . ? C8 C7 C10 C13 -40.1(5) . . . . ? C13 C10 C11 N4 1.3(5) . . . . ? C7 C10 C11 N4 -178.5(3) . . . . ? C11 C10 C13 N3 -1.8(5) . . . . ? C7 C10 C13 N3 178.0(3) . . . . ? O1 C14 C15 C16 -178.5(3) . . . . ? C19 C14 C15 C16 0.2(5) . . . . ? C14 C15 C16 O2 -179.5(3) . . . . ? C14 C15 C16 C17 1.3(5) . . . . ? O2 C16 C17 C18 178.9(3) . . . . ? C15 C16 C17 C18 -2.0(5) . . . . ? C16 C17 C18 C19 1.1(5) . . . . ? C17 C18 C19 C14 0.4(6) . . . . ? O1 C14 C19 C18 177.7(3) . . . . ? C15 C14 C19 C18 -1.1(5) . . . . ? N2 C1 N1 C2 -0.6(4) . . . . ? C3 C2 N1 C1 0.8(5) . . . . ? N1 C1 N2 C3 0.2(4) . . . . ? N1 C1 N2 C4 177.7(3) . . . . ? C2 C3 N2 C1 0.3(4) . . . . ? C2 C3 N2 C4 -177.3(3) . . . . ? C9 C4 N2 C1 -145.9(3) . . . . ? C5 C4 N2 C1 34.2(5) . . . . ? C9 C4 N2 C3 31.1(5) . . . . ? C5 C4 N2 C3 -148.8(3) . . . . ? N4 C12 N3 C13 -0.1(6) . . . . ? C10 C13 N3 C12 1.2(5) . . . . ? N3 C12 N4 C11 -0.4(6) . . . . ? C10 C11 N4 C12 -0.3(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 O1 H1A N1 0.82 1.94 2.736(4) 165.1 3_677 O2 H2A N4 0.82 1.96 2.761(4) 165.5 2_546 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.154 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.037 data_1 _database_code_depnum_ccdc_archive 'CCDC 874492' #TrackingRef 'web_deposit_cif_file_0_Gui-GeHou_1333420859.1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H10 N3 O' _chemical_formula_weight 212.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 9.865(2) _cell_length_b 15.655(4) _cell_length_c 14.016(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.089(3) _cell_angle_gamma 90.00 _cell_volume 2124.3(8) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1186 _cell_measurement_theta_min 2.473 _cell_measurement_theta_max 22.199 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.327 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'smart APEX' _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 5471 _diffrn_reflns_av_R_equivalents 0.0229 _diffrn_reflns_av_sigmaI/netI 0.0291 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 25.50 _reflns_number_total 1982 _reflns_number_gt 1397 _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, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0657P)^2^+0.8537P] 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 1982 _refine_ls_number_parameters 147 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0850 _refine_ls_R_factor_gt 0.0594 _refine_ls_wR_factor_ref 0.1542 _refine_ls_wR_factor_gt 0.1398 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _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 0.5111(3) 0.53461(17) 0.11907(19) 0.0730(7) Uani 1 1 d . . . H1 H 0.5904 0.5022 0.1202 0.088 Uiso 1 1 calc R . . C2 C 0.5236(2) 0.62202(16) 0.12066(18) 0.0622(7) Uani 1 1 d . . . H2 H 0.6096 0.6472 0.1229 0.075 Uiso 1 1 calc R . . C3 C 0.4085(2) 0.67245(15) 0.11893(14) 0.0488(5) Uani 1 1 d . . . C4 C 0.2863(2) 0.62988(17) 0.1183(2) 0.0727(8) Uani 1 1 d . . . H4 H 0.2056 0.6604 0.1189 0.087 Uiso 1 1 calc R . . C5 C 0.2839(3) 0.54236(19) 0.1166(2) 0.0880(9) Uani 1 1 d . . . H5 H 0.1997 0.5154 0.1158 0.106 Uiso 1 1 calc R . . C6 C 0.5105(2) 0.81004(15) 0.07628(18) 0.0610(6) Uani 1 1 d . . . H6 H 0.5763 0.7784 0.0521 0.073 Uiso 1 1 calc R . . C7 C 0.4146(2) 0.76669(15) 0.11742(15) 0.0507(6) Uani 1 1 d . . . C8 C 0.3244(3) 0.81794(18) 0.1549(2) 0.0791(8) Uani 1 1 d . . . H8 H 0.2591 0.7920 0.1851 0.095 Uiso 1 1 calc R . . C9 C 0.4216(3) 0.93610(19) 0.1062(2) 0.0886(9) Uani 1 1 d . . . H9 H 0.4231 0.9953 0.1011 0.106 Uiso 1 1 calc R . . C10 C 0.5000 0.32081(19) 0.2500 0.0522(8) Uani 1 2 d S . . H10 H 0.5000 0.3802 0.2500 0.063 Uiso 1 2 calc SR . . C11 C 0.4297(2) 0.27721(14) 0.17038(17) 0.0538(6) Uani 1 1 d . . . C12 C 0.4287(3) 0.18894(15) 0.17016(19) 0.0662(7) Uani 1 1 d . . . H12 H 0.3807 0.1588 0.1171 0.079 Uiso 1 1 calc R . . C13 C 0.5000 0.1469(2) 0.2500 0.0756(11) Uani 1 2 d S . . H13 H 0.5000 0.0875 0.2500 0.091 Uiso 1 2 calc SR . . N1 N 0.3931(3) 0.49379(14) 0.11610(16) 0.0764(7) Uani 1 1 d . . . N2 N 0.5142(2) 0.89454(14) 0.06925(18) 0.0811(7) Uani 1 1 d . . . N3 N 0.3260(3) 0.90357(16) 0.1500(2) 0.0988(8) Uani 1 1 d . . . O2 O 0.3601(2) 0.31882(11) 0.09090(12) 0.0748(6) Uani 1 1 d . . . H2A H 0.3669 0.3705 0.0999 0.112 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0764(18) 0.0619(17) 0.0843(18) 0.0091(14) 0.0248(14) 0.0157(15) C2 0.0542(14) 0.0583(15) 0.0775(17) 0.0062(12) 0.0208(12) 0.0016(12) C3 0.0466(12) 0.0535(13) 0.0463(12) 0.0069(10) 0.0089(9) -0.0005(10) C4 0.0498(14) 0.0657(17) 0.102(2) 0.0214(15) 0.0135(13) 0.0013(12) C5 0.0678(17) 0.0667(19) 0.123(3) 0.0299(17) 0.0012(16) -0.0149(15) C6 0.0585(14) 0.0495(14) 0.0776(16) -0.0056(12) 0.0198(12) -0.0045(11) C7 0.0500(12) 0.0529(13) 0.0494(12) -0.0019(10) 0.0101(10) -0.0005(11) C8 0.0801(18) 0.0720(19) 0.095(2) 0.0001(15) 0.0417(16) 0.0100(15) C9 0.108(2) 0.0470(16) 0.112(2) -0.0136(16) 0.024(2) -0.0072(17) C10 0.0604(19) 0.0322(15) 0.068(2) 0.000 0.0221(16) 0.000 C11 0.0579(13) 0.0430(13) 0.0660(14) -0.0010(11) 0.0256(11) -0.0010(11) C12 0.0888(18) 0.0436(14) 0.0740(16) -0.0104(12) 0.0355(14) -0.0141(13) C13 0.120(3) 0.0314(17) 0.088(3) 0.000 0.053(3) 0.000 N1 0.0878(17) 0.0527(13) 0.0841(16) 0.0171(11) 0.0053(13) -0.0044(12) N2 0.0847(16) 0.0485(13) 0.1121(19) -0.0093(12) 0.0241(14) -0.0108(12) N3 0.118(2) 0.0668(17) 0.122(2) -0.0138(15) 0.0471(18) 0.0201(15) O2 0.0925(13) 0.0540(10) 0.0726(11) -0.0063(9) 0.0030(10) -0.0020(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 C1 N1 1.322(3) . ? C1 C2 1.374(3) . ? C1 H1 0.9300 . ? C2 C3 1.380(3) . ? C2 H2 0.9300 . ? C3 C4 1.376(3) . ? C3 C7 1.477(3) . ? C4 C5 1.371(4) . ? C4 H4 0.9300 . ? C5 N1 1.319(3) . ? C5 H5 0.9300 . ? C6 N2 1.328(3) . ? C6 C7 1.378(3) . ? C6 H6 0.9300 . ? C7 C8 1.375(3) . ? C8 N3 1.342(3) . ? C8 H8 0.9300 . ? C9 N2 1.307(4) . ? C9 N3 1.322(4) . ? C9 H9 0.9300 . ? C10 C11 1.377(3) . ? C10 C11 1.377(3) 2_655 ? C10 H10 0.9300 . ? C11 O2 1.357(3) . ? C11 C12 1.382(3) . ? C12 C13 1.371(3) . ? C12 H12 0.9300 . ? C13 C12 1.371(3) 2_655 ? C13 H13 0.9300 . ? O2 H2A 0.8200 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 123.9(2) . . ? N1 C1 H1 118.0 . . ? C2 C1 H1 118.0 . . ? C1 C2 C3 119.9(2) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C4 C3 C2 116.1(2) . . ? C4 C3 C7 121.5(2) . . ? C2 C3 C7 122.4(2) . . ? C5 C4 C3 119.8(3) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? N1 C5 C4 124.4(3) . . ? N1 C5 H5 117.8 . . ? C4 C5 H5 117.8 . . ? N2 C6 C7 123.5(2) . . ? N2 C6 H6 118.2 . . ? C7 C6 H6 118.2 . . ? C8 C7 C6 114.8(2) . . ? C8 C7 C3 123.1(2) . . ? C6 C7 C3 122.1(2) . . ? N3 C8 C7 123.3(3) . . ? N3 C8 H8 118.4 . . ? C7 C8 H8 118.4 . . ? N2 C9 N3 127.4(3) . . ? N2 C9 H9 116.3 . . ? N3 C9 H9 116.3 . . ? C11 C10 C11 120.5(3) . 2_655 ? C11 C10 H10 119.7 . . ? C11 C10 H10 119.7 2_655 . ? O2 C11 C10 121.6(2) . . ? O2 C11 C12 118.4(2) . . ? C10 C11 C12 120.0(2) . . ? C13 C12 C11 118.5(3) . . ? C13 C12 H12 120.8 . . ? C11 C12 H12 120.8 . . ? C12 C13 C12 122.6(3) 2_655 . ? C12 C13 H13 118.7 2_655 . ? C12 C13 H13 118.7 . . ? C5 N1 C1 115.9(2) . . ? C9 N2 C6 115.8(2) . . ? C9 N3 C8 115.1(2) . . ? C11 O2 H2A 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -0.1(4) . . . . ? C1 C2 C3 C4 1.7(3) . . . . ? C1 C2 C3 C7 -178.1(2) . . . . ? C2 C3 C4 C5 -1.8(4) . . . . ? C7 C3 C4 C5 178.0(2) . . . . ? C3 C4 C5 N1 0.4(5) . . . . ? N2 C6 C7 C8 -2.5(4) . . . . ? N2 C6 C7 C3 176.4(2) . . . . ? C4 C3 C7 C8 28.1(3) . . . . ? C2 C3 C7 C8 -152.2(2) . . . . ? C4 C3 C7 C6 -150.6(2) . . . . ? C2 C3 C7 C6 29.1(3) . . . . ? C6 C7 C8 N3 1.7(4) . . . . ? C3 C7 C8 N3 -177.1(3) . . . . ? C11 C10 C11 O2 -179.7(2) 2_655 . . . ? C11 C10 C11 C12 0.34(16) 2_655 . . . ? O2 C11 C12 C13 179.38(17) . . . . ? C10 C11 C12 C13 -0.7(3) . . . . ? C11 C12 C13 C12 0.33(15) . . . 2_655 ? C4 C5 N1 C1 1.2(4) . . . . ? C2 C1 N1 C5 -1.3(4) . . . . ? N3 C9 N2 C6 0.5(5) . . . . ? C7 C6 N2 C9 1.5(4) . . . . ? N2 C9 N3 C8 -1.2(5) . . . . ? C7 C8 N3 C9 0.0(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 O2 H2A N1 0.82 1.95 2.773(3) 176.1 . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.135 _refine_diff_density_min -0.211 _refine_diff_density_rms 0.034 data_2 _database_code_depnum_ccdc_archive 'CCDC 874493' #TrackingRef 'web_deposit_cif_file_1_Gui-GeHou_1333420859.2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H10 N3 O' _chemical_formula_weight 212.23 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 7.352(2) _cell_length_b 9.030(3) _cell_length_c 9.219(3) _cell_angle_alpha 116.322(4) _cell_angle_beta 93.538(4) _cell_angle_gamma 108.236(4) _cell_volume 506.3(3) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1031 _cell_measurement_theta_min 2.536 _cell_measurement_theta_max 26.419 _exptl_crystal_description plan _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.392 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 222 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'smart APEX' _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 2665 _diffrn_reflns_av_R_equivalents 0.0149 _diffrn_reflns_av_sigmaI/netI 0.0304 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.54 _diffrn_reflns_theta_max 25.49 _reflns_number_total 1842 _reflns_number_gt 1530 _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, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0754P)^2^+0.3830P] 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 1842 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0758 _refine_ls_R_factor_gt 0.0660 _refine_ls_wR_factor_ref 0.1780 _refine_ls_wR_factor_gt 0.1693 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 0.3366(4) 0.9502(4) 1.2918(3) 0.0513(7) Uani 1 1 d . . . H1 H 0.3775 1.0242 1.4066 0.062 Uiso 1 1 calc R . . C2 C 0.3172(4) 1.0267(3) 1.1949(3) 0.0429(6) Uani 1 1 d . . . H2 H 0.3473 1.1490 1.2443 0.052 Uiso 1 1 calc R . . C3 C 0.2531(4) 0.9223(3) 1.0250(3) 0.0460(6) Uani 1 1 d . . . C4 C 0.2180(9) 0.7444(4) 0.9632(4) 0.1098(18) Uani 1 1 d . . . H4 H 0.1760 0.6670 0.8489 0.132 Uiso 1 1 calc R . . C5 C 0.2448(8) 0.6806(5) 1.0697(5) 0.1082(18) Uani 1 1 d . . . H5 H 0.2217 0.5597 1.0235 0.130 Uiso 1 1 calc R . . C6 C 0.1485(4) 0.8903(4) 0.7461(3) 0.0523(7) Uani 1 1 d . . . H6 H 0.1254 0.7694 0.6996 0.063 Uiso 1 1 calc R . . C7 C 0.2192(4) 0.9950(3) 0.9145(3) 0.0439(6) Uani 1 1 d . . . C8 C 0.2525(8) 1.1710(4) 0.9710(4) 0.1002(16) Uani 1 1 d . . . H8 H 0.3028 1.2494 1.0845 0.120 Uiso 1 1 calc R . . C9 C 0.1473(4) 1.1225(4) 0.7165(4) 0.0586(8) Uani 1 1 d . . . H9 H 0.1201 1.1666 0.6473 0.070 Uiso 1 1 calc R . . C10 C 0.6501(4) 0.4644(3) 0.5607(3) 0.0390(6) Uani 1 1 d . . . C11 C 0.4718(4) 0.4292(3) 0.6054(3) 0.0406(6) Uani 1 1 d . . . H11 H 0.4524 0.3821 0.6773 0.049 Uiso 1 1 calc R . . C12 C 0.3223(4) 0.4632(3) 0.5445(3) 0.0411(6) Uani 1 1 d . . . H12 H 0.2025 0.4372 0.5744 0.049 Uiso 1 1 calc R . . N1 N 0.3011(4) 0.7794(3) 1.2330(3) 0.0629(7) Uani 1 1 d . . . N2 N 0.1106(4) 0.9506(4) 0.6449(3) 0.0614(7) Uani 1 1 d . . . N3 N 0.2177(6) 1.2374(4) 0.8743(4) 0.0970(12) Uani 1 1 d . . . O1 O 0.8022(3) 0.4323(3) 0.6166(3) 0.0585(6) Uani 1 1 d . . . H1A H 0.7618 0.3681 0.6579 0.088 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0633(17) 0.0560(17) 0.0393(14) 0.0248(13) 0.0087(12) 0.0269(14) C2 0.0516(15) 0.0392(14) 0.0365(13) 0.0170(11) 0.0066(11) 0.0185(11) C3 0.0628(16) 0.0397(14) 0.0376(13) 0.0199(11) 0.0101(12) 0.0210(12) C4 0.243(6) 0.0453(19) 0.0381(17) 0.0176(15) 0.014(2) 0.059(3) C5 0.226(6) 0.050(2) 0.061(2) 0.0297(18) 0.025(3) 0.065(3) C6 0.0656(17) 0.0513(16) 0.0407(14) 0.0207(12) 0.0050(12) 0.0271(14) C7 0.0531(15) 0.0405(14) 0.0387(13) 0.0222(11) 0.0085(11) 0.0146(11) C8 0.190(5) 0.0399(18) 0.0464(18) 0.0174(15) -0.021(2) 0.029(2) C9 0.0580(17) 0.068(2) 0.0610(18) 0.0480(17) 0.0075(14) 0.0138(15) C10 0.0494(14) 0.0310(12) 0.0336(12) 0.0154(10) 0.0048(10) 0.0131(10) C11 0.0560(15) 0.0348(13) 0.0315(12) 0.0201(10) 0.0101(10) 0.0119(11) C12 0.0478(14) 0.0367(13) 0.0354(12) 0.0176(11) 0.0111(10) 0.0116(11) N1 0.0933(19) 0.0629(16) 0.0555(15) 0.0385(13) 0.0211(13) 0.0426(14) N2 0.0764(17) 0.0697(17) 0.0469(14) 0.0340(13) 0.0076(12) 0.0315(14) N3 0.162(3) 0.0435(15) 0.0662(18) 0.0313(14) -0.0206(19) 0.0183(17) O1 0.0580(12) 0.0710(14) 0.0679(13) 0.0492(11) 0.0146(10) 0.0280(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 C1 N1 1.316(4) . ? C1 C2 1.374(4) . ? C1 H1 0.9300 . ? C2 C3 1.373(3) . ? C2 H2 0.9300 . ? C3 C4 1.372(4) . ? C3 C7 1.481(3) . ? C4 C5 1.373(5) . ? C4 H4 0.9300 . ? C5 N1 1.317(4) . ? C5 H5 0.9300 . ? C6 N2 1.326(3) . ? C6 C7 1.366(4) . ? C6 H6 0.9300 . ? C7 C8 1.365(4) . ? C8 N3 1.328(4) . ? C8 H8 0.9300 . ? C9 N3 1.301(4) . ? C9 N2 1.313(4) . ? C9 H9 0.9300 . ? C10 O1 1.365(3) . ? C10 C11 1.383(4) . ? C10 C12 1.383(3) 2_666 ? C11 C12 1.380(3) . ? C11 H11 0.9300 . ? C12 C10 1.383(3) 2_666 ? C12 H12 0.9300 . ? O1 H1A 0.8200 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 124.4(3) . . ? N1 C1 H1 117.8 . . ? C2 C1 H1 117.8 . . ? C3 C2 C1 119.9(2) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C4 C3 C2 115.8(2) . . ? C4 C3 C7 121.7(2) . . ? C2 C3 C7 122.5(2) . . ? C3 C4 C5 120.1(3) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? N1 C5 C4 124.3(3) . . ? N1 C5 H5 117.9 . . ? C4 C5 H5 117.9 . . ? N2 C6 C7 124.0(3) . . ? N2 C6 H6 118.0 . . ? C7 C6 H6 118.0 . . ? C8 C7 C6 113.9(3) . . ? C8 C7 C3 123.5(2) . . ? C6 C7 C3 122.7(2) . . ? N3 C8 C7 124.2(3) . . ? N3 C8 H8 117.9 . . ? C7 C8 H8 117.9 . . ? N3 C9 N2 126.7(3) . . ? N3 C9 H9 116.6 . . ? N2 C9 H9 116.6 . . ? O1 C10 C11 123.1(2) . . ? O1 C10 C12 118.0(2) . 2_666 ? C11 C10 C12 118.9(2) . 2_666 ? C12 C11 C10 120.8(2) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C11 C12 C10 120.3(2) . 2_666 ? C11 C12 H12 119.8 . . ? C10 C12 H12 119.8 2_666 . ? C1 N1 C5 115.4(3) . . ? C9 N2 C6 115.6(3) . . ? C9 N3 C8 115.6(3) . . ? C10 O1 H1A 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 1.4(5) . . . . ? C1 C2 C3 C4 -1.9(5) . . . . ? C1 C2 C3 C7 176.7(3) . . . . ? C2 C3 C4 C5 0.8(7) . . . . ? C7 C3 C4 C5 -177.8(4) . . . . ? C3 C4 C5 N1 1.0(9) . . . . ? N2 C6 C7 C8 -1.4(5) . . . . ? N2 C6 C7 C3 177.7(3) . . . . ? C4 C3 C7 C8 -179.9(4) . . . . ? C2 C3 C7 C8 1.5(5) . . . . ? C4 C3 C7 C6 1.1(5) . . . . ? C2 C3 C7 C6 -177.5(3) . . . . ? C6 C7 C8 N3 1.0(7) . . . . ? C3 C7 C8 N3 -178.0(4) . . . . ? O1 C10 C11 C12 -179.6(2) . . . . ? C12 C10 C11 C12 0.9(4) 2_666 . . . ? C10 C11 C12 C10 -0.9(4) . . . 2_666 ? C2 C1 N1 C5 0.5(5) . . . . ? C4 C5 N1 C1 -1.6(7) . . . . ? N3 C9 N2 C6 0.7(5) . . . . ? C7 C6 N2 C9 0.6(5) . . . . ? N2 C9 N3 C8 -1.0(6) . . . . ? C7 C8 N3 C9 0.1(7) . . . . ? 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 O1 H1A N1 0.82 1.96 2.780(3) 173.0 2_667 _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.262 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.048