data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Hiromitsu Maeda' _publ_contact_author_address ; Department of Bioscience and Biotechnology, Faculty of Science and Engineering Ritsumeikan University 1-1-1 Nojihigashi Kusatsu Shiga 525-8577 JAPAN ; _publ_contact_author_email MAEDAHIR@SE.RITSUMEI.AC.JP _publ_section_title ; Hydrogen bonding self-assemblies with 1-D linear, dimeric and hexagonal nanostructures of meso-pyridyl-substituted dipyrromethanes ; loop_ _publ_author_name 'Hiromitsu Maeda' 'Masahiro Hasegawa' 'Atsushi Ueda' # Attachment 'dpm_hb_HMaeda_CIF.CIF' data_1 _database_code_depnum_ccdc_archive 'CCDC 637498' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H15 N3' _chemical_formula_sum 'C15 H15 N3' _chemical_formula_weight 237.30 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.510(4) _cell_length_b 10.572(6) _cell_length_c 12.645(5) _cell_angle_alpha 90.00 _cell_angle_beta 109.048(14) _cell_angle_gamma 90.00 _cell_volume 1201.8(10) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 9003 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _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 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9764 _exptl_absorpt_correction_T_max 0.9842 _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11536 _diffrn_reflns_av_R_equivalents 0.0267 _diffrn_reflns_av_sigmaI/netI 0.0215 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2744 _reflns_number_gt 2384 _reflns_threshold_expression >2sigma(I) _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction CrystalStructure _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'CrystalStructure 3.6.0' _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^)+(0.0469P)^2^+0.5384P] 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 2744 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0476 _refine_ls_R_factor_gt 0.0410 _refine_ls_wR_factor_ref 0.1023 _refine_ls_wR_factor_gt 0.0979 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _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 0.80948(12) 0.14769(10) 0.99361(8) 0.0174(2) Uani 1 1 d . . . H1N H 0.8580 0.0826 1.0319 0.021 Uiso 1 1 calc R . . N2 N 0.88178(11) -0.04513(10) 0.69229(8) 0.0161(2) Uani 1 1 d . . . H2N H 0.8096 -0.0903 0.6465 0.019 Uiso 1 1 calc R . . N3 N 0.69081(12) -0.30126(10) 1.00204(8) 0.0184(2) Uani 1 1 d . . . C1 C 0.80114(13) 0.26481(12) 1.03760(10) 0.0177(3) Uani 1 1 d . . . H1 H 0.8457 0.2892 1.1135 0.021 Uiso 1 1 calc R . . C2 C 0.71717(13) 0.34032(11) 0.95270(10) 0.0177(3) Uani 1 1 d . . . H2 H 0.6932 0.4267 0.9587 0.021 Uiso 1 1 calc R . . C3 C 0.67224(13) 0.26545(11) 0.85350(10) 0.0163(2) Uani 1 1 d . . . H3 H 0.6124 0.2929 0.7813 0.020 Uiso 1 1 calc R . . C4 C 0.73110(12) 0.14651(11) 0.88112(9) 0.0135(2) Uani 1 1 d . . . C5 C 0.72740(12) 0.03131(11) 0.80873(9) 0.0128(2) Uani 1 1 d . . . C6 C 0.86906(13) 0.02803(11) 0.77847(9) 0.0133(2) Uani 1 1 d . . . C7 C 1.00489(13) 0.08442(11) 0.82887(10) 0.0166(3) Uani 1 1 d . . . H7 H 1.0289 0.1410 0.8906 0.020 Uiso 1 1 calc R . . C8 C 1.10285(14) 0.04249(12) 0.77167(10) 0.0199(3) Uani 1 1 d . . . H8 H 1.2043 0.0656 0.7883 0.024 Uiso 1 1 calc R . . C9 C 1.02370(14) -0.03717(12) 0.68834(10) 0.0193(3) Uani 1 1 d . . . H9 H 1.0607 -0.0796 0.6367 0.023 Uiso 1 1 calc R . . C10 C 0.59057(13) 0.03952(12) 0.70174(10) 0.0173(3) Uani 1 1 d . . . H10A H 0.4997 0.0417 0.7222 0.021 Uiso 1 1 calc R . . H10B H 0.5883 -0.0345 0.6546 0.021 Uiso 1 1 calc R . . H10C H 0.5968 0.1166 0.6605 0.021 Uiso 1 1 calc R . . C11 C 0.71268(12) -0.08906(10) 0.87282(9) 0.0129(2) Uani 1 1 d . . . C12 C 0.79947(13) -0.19610(11) 0.87846(9) 0.0147(2) Uani 1 1 d . . . H12 H 0.8685 -0.1994 0.8386 0.018 Uiso 1 1 calc R . . C13 C 0.78432(14) -0.29822(11) 0.94293(10) 0.0173(3) Uani 1 1 d . . . H13 H 0.8444 -0.3706 0.9452 0.021 Uiso 1 1 calc R . . C14 C 0.60238(14) -0.19989(12) 0.99254(10) 0.0186(3) Uani 1 1 d . . . H14 H 0.5316 -0.2006 1.0310 0.022 Uiso 1 1 calc R . . C15 C 0.60931(13) -0.09451(11) 0.92951(10) 0.0173(3) Uani 1 1 d . . . H15 H 0.5434 -0.0256 0.9249 0.021 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 0.0217(5) 0.0135(5) 0.0147(5) -0.0007(4) 0.0030(4) 0.0042(4) N2 0.0190(5) 0.0156(5) 0.0150(5) -0.0022(4) 0.0071(4) -0.0026(4) N3 0.0226(5) 0.0153(5) 0.0174(5) 0.0005(4) 0.0068(4) -0.0031(4) C1 0.0187(6) 0.0165(6) 0.0177(6) -0.0060(5) 0.0060(5) -0.0006(4) C2 0.0188(6) 0.0121(6) 0.0242(6) -0.0020(5) 0.0097(5) -0.0002(4) C3 0.0172(6) 0.0140(6) 0.0177(6) 0.0016(4) 0.0058(5) 0.0013(4) C4 0.0144(5) 0.0127(6) 0.0138(5) -0.0002(4) 0.0053(4) -0.0005(4) C5 0.0149(5) 0.0114(5) 0.0121(5) 0.0003(4) 0.0045(4) 0.0002(4) C6 0.0180(6) 0.0112(5) 0.0114(5) 0.0015(4) 0.0057(4) 0.0005(4) C7 0.0182(6) 0.0163(6) 0.0143(5) 0.0008(4) 0.0040(5) -0.0019(4) C8 0.0160(6) 0.0245(7) 0.0194(6) 0.0044(5) 0.0062(5) -0.0011(5) C9 0.0207(6) 0.0217(6) 0.0191(6) 0.0019(5) 0.0116(5) 0.0023(5) C10 0.0162(6) 0.0196(6) 0.0146(5) 0.0004(4) 0.0030(5) -0.0004(4) C11 0.0151(5) 0.0115(5) 0.0108(5) -0.0013(4) 0.0026(4) -0.0024(4) C12 0.0160(5) 0.0144(6) 0.0144(5) -0.0005(4) 0.0060(5) 0.0001(4) C13 0.0206(6) 0.0134(6) 0.0176(6) 0.0001(4) 0.0057(5) 0.0012(4) C14 0.0204(6) 0.0187(6) 0.0191(6) -0.0011(5) 0.0099(5) -0.0026(5) C15 0.0186(6) 0.0157(6) 0.0192(6) -0.0004(5) 0.0082(5) 0.0011(4) _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 1.3703(17) . ? N1 C4 1.3738(16) . ? N1 H1N 0.8800 . ? N2 C9 1.3694(17) . ? N2 C6 1.3735(16) . ? N2 H2N 0.8800 . ? N3 C13 1.3358(17) . ? N3 C14 1.3432(17) . ? C1 C2 1.3668(18) . ? C1 H1 0.9500 . ? C2 C3 1.4257(17) . ? C2 H2 0.9500 . ? C3 C4 1.3743(17) . ? C3 H3 0.9500 . ? C4 C5 1.5171(17) . ? C5 C6 1.5163(17) . ? C5 C11 1.5394(17) . ? C5 C10 1.5435(17) . ? C6 C7 1.3758(17) . ? C7 C8 1.4240(18) . ? C7 H7 0.9500 . ? C8 C9 1.3669(19) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.3887(17) . ? C11 C15 1.3942(17) . ? C12 C13 1.3885(17) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C15 1.3840(18) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C4 110.17(10) . . ? C1 N1 H1N 124.9 . . ? C4 N1 H1N 124.9 . . ? C9 N2 C6 109.72(10) . . ? C9 N2 H2N 125.1 . . ? C6 N2 H2N 125.1 . . ? C13 N3 C14 116.26(11) . . ? C2 C1 N1 107.78(11) . . ? C2 C1 H1 126.1 . . ? N1 C1 H1 126.1 . . ? C1 C2 C3 107.30(11) . . ? C1 C2 H2 126.4 . . ? C3 C2 H2 126.4 . . ? C4 C3 C2 107.71(11) . . ? C4 C3 H3 126.1 . . ? C2 C3 H3 126.1 . . ? N1 C4 C3 107.05(10) . . ? N1 C4 C5 122.00(10) . . ? C3 C4 C5 130.84(11) . . ? C6 C5 C4 108.85(9) . . ? C6 C5 C11 110.79(9) . . ? C4 C5 C11 109.52(10) . . ? C6 C5 C10 110.15(10) . . ? C4 C5 C10 109.31(10) . . ? C11 C5 C10 108.21(9) . . ? N2 C6 C7 107.40(10) . . ? N2 C6 C5 121.91(10) . . ? C7 C6 C5 130.57(11) . . ? C6 C7 C8 107.50(11) . . ? C6 C7 H7 126.2 . . ? C8 C7 H7 126.2 . . ? C9 C8 C7 107.24(11) . . ? C9 C8 H8 126.4 . . ? C7 C8 H8 126.4 . . ? C8 C9 N2 108.12(11) . . ? C8 C9 H9 125.9 . . ? N2 C9 H9 125.9 . . ? C5 C10 H10A 109.5 . . ? C5 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C5 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C15 116.55(11) . . ? C12 C11 C5 123.09(11) . . ? C15 C11 C5 120.36(10) . . ? C13 C12 C11 119.34(11) . . ? C13 C12 H12 120.3 . . ? C11 C12 H12 120.3 . . ? N3 C13 C12 124.25(11) . . ? N3 C13 H13 117.9 . . ? C12 C13 H13 117.9 . . ? N3 C14 C15 123.21(12) . . ? N3 C14 H14 118.4 . . ? C15 C14 H14 118.4 . . ? C14 C15 C11 120.23(11) . . ? C14 C15 H15 119.9 . . ? C11 C15 H15 119.9 . . ? 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 C4 N1 C1 C2 -0.28(14) . . . . ? N1 C1 C2 C3 0.35(14) . . . . ? C1 C2 C3 C4 -0.30(14) . . . . ? C1 N1 C4 C3 0.09(13) . . . . ? C1 N1 C4 C5 176.62(10) . . . . ? C2 C3 C4 N1 0.13(13) . . . . ? C2 C3 C4 C5 -175.98(11) . . . . ? N1 C4 C5 C6 -80.23(13) . . . . ? C3 C4 C5 C6 95.39(14) . . . . ? N1 C4 C5 C11 41.04(14) . . . . ? C3 C4 C5 C11 -143.35(12) . . . . ? N1 C4 C5 C10 159.43(10) . . . . ? C3 C4 C5 C10 -24.96(17) . . . . ? C9 N2 C6 C7 0.77(13) . . . . ? C9 N2 C6 C5 -175.79(10) . . . . ? C4 C5 C6 N2 -163.27(10) . . . . ? C11 C5 C6 N2 76.24(13) . . . . ? C10 C5 C6 N2 -43.45(14) . . . . ? C4 C5 C6 C7 21.05(16) . . . . ? C11 C5 C6 C7 -99.44(14) . . . . ? C10 C5 C6 C7 140.88(13) . . . . ? N2 C6 C7 C8 -0.65(13) . . . . ? C5 C6 C7 C8 175.50(11) . . . . ? C6 C7 C8 C9 0.30(14) . . . . ? C7 C8 C9 N2 0.17(14) . . . . ? C6 N2 C9 C8 -0.58(14) . . . . ? C6 C5 C11 C12 -13.50(15) . . . . ? C4 C5 C11 C12 -133.59(11) . . . . ? C10 C5 C11 C12 107.34(13) . . . . ? C6 C5 C11 C15 166.12(10) . . . . ? C4 C5 C11 C15 46.03(14) . . . . ? C10 C5 C11 C15 -73.04(13) . . . . ? C15 C11 C12 C13 -2.97(16) . . . . ? C5 C11 C12 C13 176.66(10) . . . . ? C14 N3 C13 C12 3.23(17) . . . . ? C11 C12 C13 N3 -0.41(18) . . . . ? C13 N3 C14 C15 -2.64(18) . . . . ? N3 C14 C15 C11 -0.72(19) . . . . ? C12 C11 C15 C14 3.51(17) . . . . ? C5 C11 C15 C14 -176.14(10) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.274 _refine_diff_density_min -0.296 _refine_diff_density_rms 0.064 #============================================================================== # End of CIF #============================================================================== data_2 _database_code_depnum_ccdc_archive 'CCDC 637499' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H15 N3' _chemical_formula_sum 'C15 H15 N3' _chemical_formula_weight 237.30 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P c c n' _symmetry_space_group_name_Hall '-P 2ab 2ac' _symmetry_Int_Tables_number 56 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' '-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 27.092(7) _cell_length_b 14.512(6) _cell_length_c 6.1410(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2414.3(13) _cell_formula_units_Z 8 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 17209 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.6 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.306 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9612 _exptl_absorpt_correction_T_max 0.9803 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21485 _diffrn_reflns_av_R_equivalents 0.0269 _diffrn_reflns_av_sigmaI/netI 0.0150 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2751 _reflns_number_gt 2355 _reflns_threshold_expression >2sigma(I) _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction CrystalStructure _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'CrystalStructure 3.6.0' _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^)+(0.0799P)^2^+1.6210P] 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 2751 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0595 _refine_ls_R_factor_gt 0.0525 _refine_ls_wR_factor_ref 0.1487 _refine_ls_wR_factor_gt 0.1434 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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 0.88873(5) 0.63258(9) -0.0305(2) 0.0224(3) Uani 1 1 d . . . H1N H 0.9211 0.6360 -0.0405 0.027 Uiso 1 1 calc R . . N2 N 0.82313(5) 0.48804(10) 0.5422(2) 0.0257(3) Uani 1 1 d . . . H2N H 0.8234 0.5464 0.5808 0.031 Uiso 1 1 calc R . . N3 N 1.00042(5) 0.36441(10) 0.0741(3) 0.0319(4) Uani 1 1 d . . . C1 C 0.85597(7) 0.68552(11) -0.1463(3) 0.0284(4) Uani 1 1 d . . . H1 H 0.8642 0.7314 -0.2505 0.034 Uiso 1 1 calc R . . C2 C 0.80934(7) 0.66053(12) -0.0852(3) 0.0333(4) Uani 1 1 d . . . H2 H 0.7794 0.6859 -0.1391 0.040 Uiso 1 1 calc R . . C3 C 0.81376(6) 0.58942(11) 0.0746(3) 0.0263(4) Uani 1 1 d . . . H3 H 0.7874 0.5590 0.1470 0.032 Uiso 1 1 calc R . . C4 C 0.86324(5) 0.57333(10) 0.1038(2) 0.0187(3) Uani 1 1 d . . . C5 C 0.88965(5) 0.50732(10) 0.2560(2) 0.0183(3) Uani 1 1 d . . . C6 C 0.85223(5) 0.45004(10) 0.3814(2) 0.0195(3) Uani 1 1 d . . . C7 C 0.84114(5) 0.35795(11) 0.3682(3) 0.0258(4) Uani 1 1 d . . . H7 H 0.8556 0.3148 0.2709 0.031 Uiso 1 1 calc R . . C8 C 0.80416(6) 0.33876(13) 0.5266(3) 0.0367(4) Uani 1 1 d . . . H8 H 0.7894 0.2806 0.5544 0.044 Uiso 1 1 calc R . . C9 C 0.79361(6) 0.42153(14) 0.6334(3) 0.0328(4) Uani 1 1 d . . . H9 H 0.7704 0.4301 0.7475 0.039 Uiso 1 1 calc R . . C10 C 0.92039(6) 0.56368(11) 0.4204(3) 0.0246(3) Uani 1 1 d . . . H10A H 0.9376 0.5216 0.5194 0.030 Uiso 1 1 calc R . . H10B H 0.8985 0.6039 0.5045 0.030 Uiso 1 1 calc R . . H10C H 0.9446 0.6013 0.3417 0.030 Uiso 1 1 calc R . . C11 C 0.92214(5) 0.44193(10) 0.1224(2) 0.0191(3) Uani 1 1 d . . . C12 C 0.97056(6) 0.42109(11) 0.1821(3) 0.0277(4) Uani 1 1 d . . . H12 H 0.9832 0.4496 0.3098 0.033 Uiso 1 1 calc R . . C13 C 0.98102(6) 0.32436(11) -0.0986(3) 0.0285(4) Uani 1 1 d . . . H13 H 1.0010 0.2813 -0.1746 0.034 Uiso 1 1 calc R . . C14 C 0.93424(6) 0.33978(11) -0.1779(3) 0.0246(3) Uani 1 1 d . . . H14 H 0.9230 0.3097 -0.3060 0.030 Uiso 1 1 calc R . . C15 C 0.90406(6) 0.40041(11) -0.0655(3) 0.0235(3) Uani 1 1 d . . . H15 H 0.8716 0.4134 -0.1158 0.028 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 0.0266(6) 0.0198(6) 0.0208(6) 0.0005(5) 0.0021(5) 0.0004(5) N2 0.0233(6) 0.0285(7) 0.0253(7) 0.0001(5) 0.0037(5) 0.0004(5) N3 0.0282(7) 0.0283(7) 0.0392(8) 0.0001(6) 0.0031(6) 0.0017(6) C1 0.0467(10) 0.0187(7) 0.0200(7) 0.0003(6) -0.0022(7) 0.0047(6) C2 0.0361(9) 0.0287(8) 0.0353(9) -0.0029(7) -0.0116(8) 0.0137(7) C3 0.0204(7) 0.0262(8) 0.0325(8) 0.0005(6) -0.0014(6) 0.0033(6) C4 0.0215(7) 0.0162(6) 0.0185(7) -0.0008(5) 0.0019(6) 0.0006(5) C5 0.0171(6) 0.0184(7) 0.0195(7) 0.0011(5) 0.0002(5) 0.0002(5) C6 0.0168(6) 0.0219(7) 0.0196(7) 0.0025(5) 0.0000(5) 0.0011(5) C7 0.0213(7) 0.0223(8) 0.0336(9) 0.0026(6) -0.0012(6) -0.0013(6) C8 0.0249(8) 0.0378(9) 0.0474(11) 0.0202(8) -0.0079(8) -0.0096(7) C9 0.0203(7) 0.0537(11) 0.0245(8) 0.0125(8) 0.0017(6) -0.0014(7) C10 0.0237(7) 0.0280(8) 0.0220(7) 0.0005(6) -0.0012(6) -0.0053(6) C11 0.0200(7) 0.0167(7) 0.0207(7) 0.0040(5) 0.0034(6) 0.0008(5) C12 0.0225(7) 0.0285(8) 0.0320(9) 0.0067(7) 0.0025(6) 0.0028(6) C13 0.0310(8) 0.0203(8) 0.0343(9) 0.0034(6) 0.0053(7) -0.0034(6) C14 0.0321(8) 0.0217(7) 0.0200(7) -0.0028(6) 0.0020(6) -0.0017(6) C15 0.0224(7) 0.0225(7) 0.0254(8) -0.0011(6) -0.0010(6) 0.0023(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.373(2) . ? N1 C4 1.3772(19) . ? N1 H1N 0.8800 . ? N2 C9 1.373(2) . ? N2 C6 1.3788(19) . ? N2 H2N 0.8800 . ? N3 C13 1.319(2) . ? N3 C12 1.331(2) . ? C1 C2 1.367(3) . ? C1 H1 0.9500 . ? C2 C3 1.429(2) . ? C2 H2 0.9500 . ? C3 C4 1.372(2) . ? C3 H3 0.9500 . ? C4 C5 1.518(2) . ? C5 C6 1.5204(19) . ? C5 C11 1.532(2) . ? C5 C10 1.543(2) . ? C6 C7 1.372(2) . ? C7 C8 1.424(2) . ? C7 H7 0.9500 . ? C8 C9 1.398(3) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C15 1.391(2) . ? C11 C12 1.395(2) . ? C12 H12 0.9500 . ? C13 C14 1.376(2) . ? C13 H13 0.9500 . ? C14 C15 1.385(2) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C4 109.61(13) . . ? C1 N1 H1N 125.2 . . ? C4 N1 H1N 125.2 . . ? C9 N2 C6 110.12(14) . . ? C9 N2 H2N 124.9 . . ? C6 N2 H2N 124.9 . . ? C13 N3 C12 115.54(15) . . ? C2 C1 N1 107.86(14) . . ? C2 C1 H1 126.1 . . ? N1 C1 H1 126.1 . . ? C1 C2 C3 107.62(14) . . ? C1 C2 H2 126.2 . . ? C3 C2 H2 126.2 . . ? C4 C3 C2 107.13(15) . . ? C4 C3 H3 126.4 . . ? C2 C3 H3 126.4 . . ? C3 C4 N1 107.78(13) . . ? C3 C4 C5 130.43(14) . . ? N1 C4 C5 121.76(13) . . ? C4 C5 C6 110.03(11) . . ? C4 C5 C11 109.39(12) . . ? C6 C5 C11 108.40(12) . . ? C4 C5 C10 108.83(12) . . ? C6 C5 C10 108.57(12) . . ? C11 C5 C10 111.61(12) . . ? C7 C6 N2 107.86(13) . . ? C7 C6 C5 130.43(14) . . ? N2 C6 C5 121.69(13) . . ? C6 C7 C8 107.71(15) . . ? C6 C7 H7 126.1 . . ? C8 C7 H7 126.1 . . ? C9 C8 C7 107.24(15) . . ? C9 C8 H8 126.4 . . ? C7 C8 H8 126.4 . . ? N2 C9 C8 107.08(15) . . ? N2 C9 H9 126.5 . . ? C8 C9 H9 126.5 . . ? C5 C10 H10A 109.5 . . ? C5 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C5 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C15 C11 C12 117.08(14) . . ? C15 C11 C5 120.67(13) . . ? C12 C11 C5 122.25(14) . . ? N3 C12 C11 125.06(17) . . ? N3 C12 H12 117.5 . . ? C11 C12 H12 117.5 . . ? N3 C13 C14 125.45(16) . . ? N3 C13 H13 117.3 . . ? C14 C13 H13 117.3 . . ? C13 C14 C15 118.09(15) . . ? C13 C14 H14 121.0 . . ? C15 C14 H14 121.0 . . ? C14 C15 C11 118.71(14) . . ? C14 C15 H15 120.6 . . ? C11 C15 H15 120.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N1 C1 C2 0.37(18) . . . . ? N1 C1 C2 C3 0.00(19) . . . . ? C1 C2 C3 C4 -0.37(19) . . . . ? C2 C3 C4 N1 0.59(18) . . . . ? C2 C3 C4 C5 178.44(15) . . . . ? C1 N1 C4 C3 -0.60(17) . . . . ? C1 N1 C4 C5 -178.68(13) . . . . ? C3 C4 C5 C6 3.1(2) . . . . ? N1 C4 C5 C6 -179.32(13) . . . . ? C3 C4 C5 C11 122.06(17) . . . . ? N1 C4 C5 C11 -60.34(17) . . . . ? C3 C4 C5 C10 -115.76(17) . . . . ? N1 C4 C5 C10 61.84(17) . . . . ? C9 N2 C6 C7 0.25(17) . . . . ? C9 N2 C6 C5 -178.40(13) . . . . ? C4 C5 C6 C7 110.73(17) . . . . ? C11 C5 C6 C7 -8.9(2) . . . . ? C10 C5 C6 C7 -130.27(17) . . . . ? C4 C5 C6 N2 -70.96(17) . . . . ? C11 C5 C6 N2 169.46(13) . . . . ? C10 C5 C6 N2 48.04(17) . . . . ? N2 C6 C7 C8 -0.19(17) . . . . ? C5 C6 C7 C8 178.30(15) . . . . ? C6 C7 C8 C9 0.06(19) . . . . ? C6 N2 C9 C8 -0.21(18) . . . . ? C7 C8 C9 N2 0.09(18) . . . . ? C4 C5 C11 C15 -45.08(17) . . . . ? C6 C5 C11 C15 74.90(16) . . . . ? C10 C5 C11 C15 -165.58(13) . . . . ? C4 C5 C11 C12 135.08(14) . . . . ? C6 C5 C11 C12 -104.94(16) . . . . ? C10 C5 C11 C12 14.58(19) . . . . ? C13 N3 C12 C11 -1.8(2) . . . . ? C15 C11 C12 N3 -0.4(2) . . . . ? C5 C11 C12 N3 179.45(14) . . . . ? C12 N3 C13 C14 3.0(2) . . . . ? N3 C13 C14 C15 -1.8(2) . . . . ? C13 C14 C15 C11 -0.7(2) . . . . ? C12 C11 C15 C14 1.6(2) . . . . ? C5 C11 C15 C14 -178.21(13) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.547 _refine_diff_density_min -0.313 _refine_diff_density_rms 0.058 #============================================================================== # End of CIF #============================================================================== data_3 _database_code_depnum_ccdc_archive 'CCDC 637500' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H15 N3' _chemical_formula_sum 'C15 H15 N3' _chemical_formula_weight 237.30 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' _symmetry_cell_setting Trigonal _symmetry_space_group_name_H-M 'R -3' _symmetry_space_group_name_Hall '-R 3' _symmetry_Int_Tables_number 148 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 27.653(8) _cell_length_b 27.653(8) _cell_length_c 8.536(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 5653(3) _cell_formula_units_Z 18 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 10205 _cell_measurement_theta_min 3.3 _cell_measurement_theta_max 27.6 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.255 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2268 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9700 _exptl_absorpt_correction_T_max 0.9962 _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17891 _diffrn_reflns_av_R_equivalents 0.1308 _diffrn_reflns_av_sigmaI/netI 0.0935 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -35 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.28 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2862 _reflns_number_gt 1660 _reflns_threshold_expression >2sigma(I) _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction CrystalStructure _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'CrystalStructure 3.6.0' _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^)+(0.0550P)^2^+2.9401P] 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 2862 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1214 _refine_ls_R_factor_gt 0.0597 _refine_ls_wR_factor_ref 0.1440 _refine_ls_wR_factor_gt 0.1200 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 N1 N 0.22590(8) 0.21203(8) 0.3228(2) 0.0310(5) Uani 1 1 d . . . H1N H 0.1905 0.1973 0.3482 0.037 Uiso 1 1 calc R . . N2 N 0.13253(7) 0.09559(8) 0.4164(2) 0.0282(5) Uani 1 1 d . . . H2N H 0.1310 0.1173 0.4893 0.034 Uiso 1 1 calc R . . N3 N 0.20532(8) 0.09267(8) 0.7004(2) 0.0312(5) Uani 1 1 d . . . C1 C 0.25642(11) 0.26132(10) 0.2442(3) 0.0354(6) Uani 1 1 d . . . H1 H 0.2432 0.2852 0.2083 0.042 Uiso 1 1 calc R . . C2 C 0.30918(11) 0.27003(11) 0.2266(3) 0.0408(7) Uani 1 1 d . . . H2 H 0.3395 0.3011 0.1766 0.049 Uiso 1 1 calc R . . C3 C 0.31050(10) 0.22425(10) 0.2967(3) 0.0352(6) Uani 1 1 d . . . H3 H 0.3419 0.2190 0.3016 0.042 Uiso 1 1 calc R . . C4 C 0.25856(9) 0.18895(9) 0.3562(2) 0.0268(5) Uani 1 1 d . . . C5 C 0.23594(9) 0.13392(9) 0.4428(3) 0.0257(5) Uani 1 1 d . . . C6 C 0.17938(9) 0.09308(9) 0.3777(3) 0.0241(5) Uani 1 1 d . . . C7 C 0.16416(10) 0.05408(9) 0.2611(3) 0.0294(5) Uani 1 1 d . . . H7 H 0.1879 0.0431 0.2113 0.035 Uiso 1 1 calc R . . C8 C 0.10679(10) 0.03296(10) 0.2278(3) 0.0330(6) Uani 1 1 d . . . H8 H 0.0852 0.0054 0.1518 0.040 Uiso 1 1 calc R . . C9 C 0.08852(10) 0.05952(10) 0.3253(3) 0.0324(6) Uani 1 1 d . . . H9 H 0.0517 0.0539 0.3292 0.039 Uiso 1 1 calc R . . C10 C 0.23163(9) 0.14105(10) 0.6195(3) 0.0253(5) Uani 1 1 d . . . C11 C 0.25413(9) 0.19233(10) 0.6935(3) 0.0299(5) Uani 1 1 d . . . H11 H 0.2726 0.2258 0.6341 0.036 Uiso 1 1 calc R . . C12 C 0.24958(10) 0.19456(10) 0.8537(3) 0.0322(6) Uani 1 1 d . . . H12 H 0.2654 0.2295 0.9062 0.039 Uiso 1 1 calc R . . C13 C 0.22183(10) 0.14544(10) 0.9362(3) 0.0345(6) Uani 1 1 d . . . H13 H 0.2172 0.1456 1.0464 0.041 Uiso 1 1 calc R . . C14 C 0.20093(10) 0.09599(11) 0.8552(3) 0.0353(6) Uani 1 1 d . . . H14 H 0.1822 0.0621 0.9129 0.042 Uiso 1 1 calc R . . C15 C 0.27646(10) 0.11161(11) 0.4185(3) 0.0356(6) Uani 1 1 d . . . H15A H 0.3132 0.1384 0.4612 0.043 Uiso 1 1 calc R . . H15B H 0.2799 0.1065 0.3063 0.043 Uiso 1 1 calc R . . H15C H 0.2621 0.0757 0.4726 0.043 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 0.0302(11) 0.0311(11) 0.0292(11) 0.0043(9) 0.0031(9) 0.0135(9) N2 0.0248(10) 0.0283(10) 0.0308(11) -0.0060(8) -0.0013(8) 0.0127(9) N3 0.0352(11) 0.0367(12) 0.0216(10) 0.0041(9) 0.0014(9) 0.0178(10) C1 0.0428(15) 0.0261(13) 0.0279(13) 0.0037(10) -0.0008(11) 0.0102(11) C2 0.0379(15) 0.0347(14) 0.0280(14) 0.0015(11) -0.0007(11) 0.0019(12) C3 0.0260(13) 0.0434(15) 0.0260(13) 0.0004(11) 0.0011(10) 0.0097(11) C4 0.0269(12) 0.0330(13) 0.0187(11) 0.0005(10) -0.0004(9) 0.0137(10) C5 0.0247(12) 0.0327(12) 0.0214(12) 0.0015(10) 0.0015(9) 0.0156(10) C6 0.0255(12) 0.0275(12) 0.0233(12) 0.0036(9) 0.0044(9) 0.0164(10) C7 0.0394(14) 0.0284(12) 0.0239(12) 0.0042(10) 0.0040(10) 0.0195(11) C8 0.0386(14) 0.0263(12) 0.0268(13) -0.0004(10) -0.0046(11) 0.0107(11) C9 0.0267(13) 0.0295(13) 0.0371(14) -0.0030(11) -0.0047(11) 0.0112(11) C10 0.0202(11) 0.0358(13) 0.0218(12) 0.0012(10) 0.0003(9) 0.0155(10) C11 0.0288(13) 0.0342(13) 0.0249(12) 0.0000(10) -0.0021(10) 0.0144(11) C12 0.0295(13) 0.0398(14) 0.0279(13) -0.0054(11) -0.0042(10) 0.0178(11) C13 0.0379(14) 0.0479(16) 0.0214(12) -0.0017(11) -0.0019(11) 0.0242(13) C14 0.0423(15) 0.0416(15) 0.0213(12) 0.0072(11) 0.0037(11) 0.0204(12) C15 0.0357(14) 0.0481(16) 0.0301(13) 0.0050(11) 0.0049(11) 0.0262(13) _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 1.367(3) . ? N1 C4 1.371(3) . ? N1 H1N 0.8800 . ? N2 C9 1.366(3) . ? N2 C6 1.372(3) . ? N2 H2N 0.8800 . ? N3 C14 1.334(3) . ? N3 C10 1.350(3) . ? C1 C2 1.363(4) . ? C1 H1 0.9500 . ? C2 C3 1.417(4) . ? C2 H2 0.9500 . ? C3 C4 1.368(3) . ? C3 H3 0.9500 . ? C4 C5 1.517(3) . ? C5 C6 1.505(3) . ? C5 C10 1.533(3) . ? C5 C15 1.540(3) . ? C6 C7 1.370(3) . ? C7 C8 1.418(3) . ? C7 H7 0.9500 . ? C8 C9 1.364(3) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 C11 1.384(3) . ? C11 C12 1.378(3) . ? C11 H11 0.9500 . ? C12 C13 1.374(3) . ? C12 H12 0.9500 . ? C13 C14 1.376(3) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C4 110.1(2) . . ? C1 N1 H1N 124.9 . . ? C4 N1 H1N 124.9 . . ? C9 N2 C6 110.20(19) . . ? C9 N2 H2N 124.9 . . ? C6 N2 H2N 124.9 . . ? C14 N3 C10 117.4(2) . . ? C2 C1 N1 107.6(2) . . ? C2 C1 H1 126.2 . . ? N1 C1 H1 126.2 . . ? C1 C2 C3 107.4(2) . . ? C1 C2 H2 126.3 . . ? C3 C2 H2 126.3 . . ? C4 C3 C2 107.9(2) . . ? C4 C3 H3 126.1 . . ? C2 C3 H3 126.1 . . ? C3 C4 N1 107.0(2) . . ? C3 C4 C5 131.0(2) . . ? N1 C4 C5 122.07(19) . . ? C6 C5 C4 108.98(18) . . ? C6 C5 C10 109.96(18) . . ? C4 C5 C10 111.73(18) . . ? C6 C5 C15 109.93(19) . . ? C4 C5 C15 108.58(18) . . ? C10 C5 C15 107.62(18) . . ? C7 C6 N2 106.76(19) . . ? C7 C6 C5 130.9(2) . . ? N2 C6 C5 121.77(19) . . ? C6 C7 C8 108.1(2) . . ? C6 C7 H7 126.0 . . ? C8 C7 H7 126.0 . . ? C9 C8 C7 107.2(2) . . ? C9 C8 H8 126.4 . . ? C7 C8 H8 126.4 . . ? C8 C9 N2 107.8(2) . . ? C8 C9 H9 126.1 . . ? N2 C9 H9 126.1 . . ? N3 C10 C11 121.7(2) . . ? N3 C10 C5 114.4(2) . . ? C11 C10 C5 123.8(2) . . ? C12 C11 C10 119.6(2) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C13 C12 C11 118.9(2) . . ? C13 C12 H12 120.6 . . ? C11 C12 H12 120.6 . . ? C12 C13 C14 118.3(2) . . ? C12 C13 H13 120.8 . . ? C14 C13 H13 120.8 . . ? N3 C14 C13 124.0(2) . . ? N3 C14 H14 118.0 . . ? C13 C14 H14 118.0 . . ? C5 C15 H15A 109.5 . . ? C5 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C5 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 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 C4 N1 C1 C2 0.1(3) . . . . ? N1 C1 C2 C3 0.2(3) . . . . ? C1 C2 C3 C4 -0.4(3) . . . . ? C2 C3 C4 N1 0.4(3) . . . . ? C2 C3 C4 C5 180.0(2) . . . . ? C1 N1 C4 C3 -0.3(3) . . . . ? C1 N1 C4 C5 -179.9(2) . . . . ? C3 C4 C5 C6 -135.8(2) . . . . ? N1 C4 C5 C6 43.7(3) . . . . ? C3 C4 C5 C10 102.5(3) . . . . ? N1 C4 C5 C10 -78.0(3) . . . . ? C3 C4 C5 C15 -16.1(3) . . . . ? N1 C4 C5 C15 163.4(2) . . . . ? C9 N2 C6 C7 -0.7(3) . . . . ? C9 N2 C6 C5 171.2(2) . . . . ? C4 C5 C6 C7 92.6(3) . . . . ? C10 C5 C6 C7 -144.6(2) . . . . ? C15 C5 C6 C7 -26.3(3) . . . . ? C4 C5 C6 N2 -77.2(2) . . . . ? C10 C5 C6 N2 45.6(3) . . . . ? C15 C5 C6 N2 163.94(19) . . . . ? N2 C6 C7 C8 0.5(2) . . . . ? C5 C6 C7 C8 -170.4(2) . . . . ? C6 C7 C8 C9 -0.2(3) . . . . ? C7 C8 C9 N2 -0.3(3) . . . . ? C6 N2 C9 C8 0.6(3) . . . . ? C14 N3 C10 C11 1.0(3) . . . . ? C14 N3 C10 C5 179.0(2) . . . . ? C6 C5 C10 N3 50.9(2) . . . . ? C4 C5 C10 N3 172.10(18) . . . . ? C15 C5 C10 N3 -68.8(2) . . . . ? C6 C5 C10 C11 -131.2(2) . . . . ? C4 C5 C10 C11 -10.0(3) . . . . ? C15 C5 C10 C11 109.1(2) . . . . ? N3 C10 C11 C12 -0.3(3) . . . . ? C5 C10 C11 C12 -178.1(2) . . . . ? C10 C11 C12 C13 -1.1(3) . . . . ? C11 C12 C13 C14 1.6(4) . . . . ? C10 N3 C14 C13 -0.5(4) . . . . ? C12 C13 C14 N3 -0.9(4) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.214 _refine_diff_density_min -0.244 _refine_diff_density_rms 0.054 #============================================================================== # End of CIF #============================================================================== data_4 _database_code_depnum_ccdc_archive 'CCDC 637501' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H13 N3' _chemical_formula_weight 223.27 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.1012(12) _cell_length_b 9.7702(13) _cell_length_c 13.9971(19) _cell_angle_alpha 90.305(2) _cell_angle_beta 105.415(2) _cell_angle_gamma 107.982(2) _cell_volume 1136.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 4236 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 28.11 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.305 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9572 _exptl_absorpt_correction_T_max 0.9841 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6819 _diffrn_reflns_av_R_equivalents 0.0175 _diffrn_reflns_av_sigmaI/netI 0.0330 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 28.07 _reflns_number_total 4824 _reflns_number_gt 4083 _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 '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^)+(0.0443P)^2^+0.6020P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4824 _refine_ls_number_parameters 315 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0522 _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_ref 0.1087 _refine_ls_wR_factor_gt 0.1027 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 0.78144(16) 0.73009(16) 0.36690(10) 0.0172(3) Uani 1 1 d . . . H1 H 0.8267 0.6552 0.3636 0.021 Uiso 1 1 calc R . . C2 C 0.86586(17) 0.87205(16) 0.39877(10) 0.0178(3) Uani 1 1 d . . . H2 H 0.9797 0.9136 0.4214 0.021 Uiso 1 1 calc R . . C3 C 0.75219(16) 0.94590(15) 0.39175(10) 0.0171(3) Uani 1 1 d . . . H3 H 0.7754 1.0460 0.4091 0.021 Uiso 1 1 calc R . . C4 C 0.60177(16) 0.84534(15) 0.35499(10) 0.0155(3) Uani 1 1 d . . . C5 C 0.43827(16) 0.86437(15) 0.33108(10) 0.0160(3) Uani 1 1 d . . . C6 C 0.34169(17) 0.78620(15) 0.39873(10) 0.0170(3) Uani 1 1 d . . . C7 C 0.17941(17) 0.73226(16) 0.38751(11) 0.0205(3) Uani 1 1 d . . . H7 H 0.0963 0.7323 0.3296 0.025 Uiso 1 1 calc R . . C8 C 0.15801(18) 0.67627(16) 0.47820(11) 0.0216(3) Uani 1 1 d . . . H8 H 0.0580 0.6322 0.4919 0.026 Uiso 1 1 calc R . . C9 C 0.30669(18) 0.69719(16) 0.54171(11) 0.0215(3) Uani 1 1 d . . . H9 H 0.3294 0.6702 0.6078 0.026 Uiso 1 1 calc R . . C10 C 0.35225(16) 0.82122(15) 0.22074(10) 0.0160(3) Uani 1 1 d . . . C11 C 0.31556(18) 0.89367(17) 0.06244(11) 0.0213(3) Uani 1 1 d . . . H11 H 0.3321 0.9693 0.0201 0.026 Uiso 1 1 calc R . . C12 C 0.22666(17) 0.75558(17) 0.01923(11) 0.0213(3) Uani 1 1 d . . . H12 H 0.1852 0.7360 -0.0510 0.026 Uiso 1 1 calc R . . C13 C 0.19952(17) 0.64608(16) 0.08114(11) 0.0219(3) Uani 1 1 d . . . H13 H 0.1398 0.5493 0.0540 0.026 Uiso 1 1 calc R . . C14 C 0.26067(17) 0.67972(15) 0.18310(11) 0.0187(3) Uani 1 1 d . . . H14 H 0.2403 0.6068 0.2269 0.022 Uiso 1 1 calc R . . C15 C 0.78360(17) 0.23795(17) 0.23322(10) 0.0200(3) Uani 1 1 d . . . H15 H 0.8323 0.1661 0.2544 0.024 Uiso 1 1 calc R . . C16 C 0.86327(17) 0.38185(17) 0.23172(11) 0.0211(3) Uani 1 1 d . . . H16 H 0.9766 0.4277 0.2519 0.025 Uiso 1 1 calc R . . C17 C 0.74492(17) 0.44927(16) 0.19437(11) 0.0196(3) Uani 1 1 d . . . H17 H 0.7644 0.5486 0.1842 0.024 Uiso 1 1 calc R . . C18 C 0.59679(16) 0.34456(15) 0.17556(10) 0.0163(3) Uani 1 1 d . . . C19 C 0.43129(16) 0.35923(15) 0.14260(10) 0.0164(3) Uani 1 1 d . . . C20 C 0.33120(17) 0.27918(15) 0.04222(11) 0.0181(3) Uani 1 1 d . . . C21 C 0.16821(18) 0.22705(18) -0.00052(12) 0.0245(3) Uani 1 1 d . . . H21 H 0.0877 0.2291 0.0304 0.029 Uiso 1 1 calc R . . C22 C 0.14101(19) 0.16945(17) -0.09921(12) 0.0255(3) Uani 1 1 d . . . H22 H 0.0392 0.1259 -0.1463 0.031 Uiso 1 1 calc R . . C23 C 0.28744(18) 0.18784(16) -0.11427(11) 0.0224(3) Uani 1 1 d . . . H23 H 0.3064 0.1590 -0.1736 0.027 Uiso 1 1 calc R . . C24 C 0.34646(16) 0.31879(15) 0.22390(10) 0.0165(3) Uani 1 1 d . . . C25 C 0.31231(17) 0.39594(16) 0.36974(11) 0.0199(3) Uani 1 1 d . . . H25 H 0.3354 0.4717 0.4198 0.024 Uiso 1 1 calc R . . C26 C 0.21016(18) 0.26107(17) 0.37771(11) 0.0218(3) Uani 1 1 d . . . H26 H 0.1637 0.2446 0.4316 0.026 Uiso 1 1 calc R . . C27 C 0.17766(18) 0.15106(17) 0.30515(12) 0.0237(3) Uani 1 1 d . . . H27 H 0.1092 0.0567 0.3087 0.028 Uiso 1 1 calc R . . C28 C 0.24599(18) 0.17987(16) 0.22715(11) 0.0211(3) Uani 1 1 d . . . H28 H 0.2246 0.1057 0.1764 0.025 Uiso 1 1 calc R . . H5 H 0.460(2) 0.9701(19) 0.3422(12) 0.020(4) Uiso 1 1 d . . . H19 H 0.450(2) 0.4643(19) 0.1383(12) 0.020(4) Uiso 1 1 d . . . N1 N 0.62106(14) 0.71411(13) 0.34055(8) 0.0161(2) Uani 1 1 d . . . H1A H 0.5425 0.6323 0.3179 0.019 Uiso 1 1 calc R . . N2 N 0.41803(14) 0.76451(13) 0.49291(9) 0.0193(3) Uani 1 1 d . . . H2A H 0.5231 0.7900 0.5185 0.023 Uiso 1 1 calc R . . N3 N 0.37997(14) 0.92734(13) 0.16087(9) 0.0185(3) Uani 1 1 d . . . N4 N 0.62197(14) 0.21594(13) 0.19895(9) 0.0177(3) Uani 1 1 d . . . H4A H 0.5458 0.1322 0.1928 0.021 Uiso 1 1 calc R . . N5 N 0.40222(14) 0.25538(13) -0.02832(9) 0.0189(3) Uani 1 1 d . . . H5A H 0.5068 0.2800 -0.0196 0.023 Uiso 1 1 calc R . . N6 N 0.38041(14) 0.42515(13) 0.29489(9) 0.0176(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0155(6) 0.0230(7) 0.0144(6) 0.0016(5) 0.0055(5) 0.0070(5) C2 0.0135(6) 0.0230(7) 0.0146(6) 0.0021(5) 0.0039(5) 0.0025(5) C3 0.0168(7) 0.0161(7) 0.0157(6) 0.0016(5) 0.0041(5) 0.0016(5) C4 0.0154(6) 0.0170(7) 0.0132(6) 0.0017(5) 0.0044(5) 0.0038(5) C5 0.0143(6) 0.0153(7) 0.0181(7) 0.0011(5) 0.0038(5) 0.0048(5) C6 0.0169(7) 0.0181(7) 0.0168(7) 0.0007(5) 0.0044(5) 0.0069(5) C7 0.0167(7) 0.0237(8) 0.0218(7) 0.0040(6) 0.0056(6) 0.0074(6) C8 0.0203(7) 0.0233(8) 0.0243(8) 0.0035(6) 0.0105(6) 0.0080(6) C9 0.0256(7) 0.0241(8) 0.0191(7) 0.0036(6) 0.0105(6) 0.0106(6) C10 0.0130(6) 0.0180(7) 0.0184(7) 0.0027(5) 0.0045(5) 0.0070(5) C11 0.0207(7) 0.0272(8) 0.0200(7) 0.0073(6) 0.0081(6) 0.0109(6) C12 0.0170(7) 0.0313(8) 0.0168(7) 0.0004(6) 0.0032(6) 0.0108(6) C13 0.0161(7) 0.0213(7) 0.0246(8) -0.0026(6) 0.0014(6) 0.0046(6) C14 0.0168(7) 0.0173(7) 0.0205(7) 0.0029(5) 0.0029(6) 0.0051(5) C15 0.0179(7) 0.0271(8) 0.0155(7) 0.0029(6) 0.0049(5) 0.0076(6) C16 0.0153(7) 0.0275(8) 0.0175(7) -0.0012(6) 0.0052(5) 0.0023(6) C17 0.0193(7) 0.0184(7) 0.0192(7) -0.0014(5) 0.0078(6) 0.0014(5) C18 0.0173(7) 0.0168(7) 0.0147(6) 0.0001(5) 0.0059(5) 0.0041(5) C19 0.0155(6) 0.0159(7) 0.0185(7) 0.0023(5) 0.0067(5) 0.0041(5) C20 0.0182(7) 0.0191(7) 0.0190(7) 0.0028(5) 0.0074(6) 0.0071(5) C21 0.0180(7) 0.0313(8) 0.0246(8) 0.0009(6) 0.0072(6) 0.0074(6) C22 0.0223(7) 0.0277(8) 0.0218(8) 0.0011(6) 0.0017(6) 0.0052(6) C23 0.0266(8) 0.0240(8) 0.0166(7) 0.0028(6) 0.0055(6) 0.0086(6) C24 0.0147(6) 0.0170(7) 0.0185(7) 0.0020(5) 0.0050(5) 0.0060(5) C25 0.0207(7) 0.0228(7) 0.0178(7) -0.0005(6) 0.0048(6) 0.0096(6) C26 0.0212(7) 0.0288(8) 0.0189(7) 0.0051(6) 0.0094(6) 0.0098(6) C27 0.0236(8) 0.0205(7) 0.0276(8) 0.0047(6) 0.0122(6) 0.0036(6) C28 0.0237(7) 0.0176(7) 0.0229(7) -0.0006(6) 0.0108(6) 0.0043(6) N1 0.0140(5) 0.0161(6) 0.0167(6) -0.0005(4) 0.0045(4) 0.0027(4) N2 0.0159(6) 0.0251(7) 0.0168(6) 0.0011(5) 0.0035(5) 0.0076(5) N3 0.0169(6) 0.0189(6) 0.0208(6) 0.0033(5) 0.0063(5) 0.0064(5) N4 0.0162(6) 0.0183(6) 0.0172(6) 0.0020(5) 0.0050(5) 0.0032(5) N5 0.0166(6) 0.0239(6) 0.0180(6) 0.0038(5) 0.0073(5) 0.0069(5) N6 0.0164(6) 0.0187(6) 0.0181(6) 0.0011(5) 0.0044(5) 0.0068(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.3650(17) . ? C1 C2 1.366(2) . ? C1 H1 0.9500 . ? C2 C3 1.417(2) . ? C2 H2 0.9500 . ? C3 C4 1.3761(19) . ? C3 H3 0.9500 . ? C4 N1 1.3677(18) . ? C4 C5 1.5059(19) . ? C5 C6 1.5127(19) . ? C5 C10 1.5239(19) . ? C5 H5 0.993(17) . ? C6 N2 1.3683(18) . ? C6 C7 1.3707(19) . ? C7 C8 1.422(2) . ? C7 H7 0.9500 . ? C8 C9 1.361(2) . ? C8 H8 0.9500 . ? C9 N2 1.3737(19) . ? C9 H9 0.9500 . ? C10 N3 1.3420(18) . ? C10 C14 1.390(2) . ? C11 N3 1.3405(19) . ? C11 C12 1.378(2) . ? C11 H11 0.9500 . ? C12 C13 1.385(2) . ? C12 H12 0.9500 . ? C13 C14 1.384(2) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 N4 1.3671(18) . ? C15 C16 1.372(2) . ? C15 H15 0.9500 . ? C16 C17 1.418(2) . ? C16 H16 0.9500 . ? C17 C18 1.3749(19) . ? C17 H17 0.9500 . ? C18 N4 1.3715(18) . ? C18 C19 1.5055(19) . ? C19 C20 1.511(2) . ? C19 C24 1.5267(19) . ? C19 H19 0.992(17) . ? C20 C21 1.370(2) . ? C20 N5 1.3699(18) . ? C21 C22 1.418(2) . ? C21 H21 0.9500 . ? C22 C23 1.362(2) . ? C22 H22 0.9500 . ? C23 N5 1.3682(19) . ? C23 H23 0.9500 . ? C24 N6 1.3380(18) . ? C24 C28 1.3917(19) . ? C25 N6 1.3425(18) . ? C25 C26 1.383(2) . ? C25 H25 0.9500 . ? C26 C27 1.381(2) . ? C26 H26 0.9500 . ? C27 C28 1.384(2) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? N1 H1A 0.8800 . ? N2 H2A 0.8800 . ? N4 H4A 0.8800 . ? N5 H5A 0.8800 . ? 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 108.41(12) . . ? N1 C1 H1 125.8 . . ? C2 C1 H1 125.8 . . ? C1 C2 C3 107.30(12) . . ? C1 C2 H2 126.4 . . ? C3 C2 H2 126.4 . . ? C4 C3 C2 107.09(13) . . ? C4 C3 H3 126.5 . . ? C2 C3 H3 126.5 . . ? N1 C4 C3 107.97(12) . . ? N1 C4 C5 122.20(12) . . ? C3 C4 C5 129.83(13) . . ? C4 C5 C6 111.71(11) . . ? C4 C5 C10 109.74(11) . . ? C6 C5 C10 113.50(11) . . ? C4 C5 H5 105.3(10) . . ? C6 C5 H5 109.6(10) . . ? C10 C5 H5 106.6(10) . . ? N2 C6 C7 107.21(12) . . ? N2 C6 C5 120.33(12) . . ? C7 C6 C5 132.39(13) . . ? C6 C7 C8 107.59(13) . . ? C6 C7 H7 126.2 . . ? C8 C7 H7 126.2 . . ? C9 C8 C7 107.58(13) . . ? C9 C8 H8 126.2 . . ? C7 C8 H8 126.2 . . ? C8 C9 N2 107.55(13) . . ? C8 C9 H9 126.2 . . ? N2 C9 H9 126.2 . . ? N3 C10 C14 121.75(13) . . ? N3 C10 C5 115.45(12) . . ? C14 C10 C5 122.64(12) . . ? N3 C11 C12 123.66(14) . . ? N3 C11 H11 118.2 . . ? C12 C11 H11 118.2 . . ? C11 C12 C13 118.11(14) . . ? C11 C12 H12 120.9 . . ? C13 C12 H12 120.9 . . ? C14 C13 C12 118.99(14) . . ? C14 C13 H13 120.5 . . ? C12 C13 H13 120.5 . . ? C13 C14 C10 119.35(13) . . ? C13 C14 H14 120.3 . . ? C10 C14 H14 120.3 . . ? N4 C15 C16 108.16(13) . . ? N4 C15 H15 125.9 . . ? C16 C15 H15 125.9 . . ? C15 C16 C17 107.19(13) . . ? C15 C16 H16 126.4 . . ? C17 C16 H16 126.4 . . ? C18 C17 C16 107.47(13) . . ? C18 C17 H17 126.3 . . ? C16 C17 H17 126.3 . . ? N4 C18 C17 107.70(13) . . ? N4 C18 C19 122.68(12) . . ? C17 C18 C19 129.49(13) . . ? C18 C19 C20 113.57(11) . . ? C18 C19 C24 110.12(11) . . ? C20 C19 C24 112.83(11) . . ? C18 C19 H19 105.2(10) . . ? C20 C19 H19 108.9(10) . . ? C24 C19 H19 105.6(9) . . ? C21 C20 N5 106.87(13) . . ? C21 C20 C19 131.95(13) . . ? N5 C20 C19 121.04(12) . . ? C20 C21 C22 107.81(13) . . ? C20 C21 H21 126.1 . . ? C22 C21 H21 126.1 . . ? C23 C22 C21 107.53(14) . . ? C23 C22 H22 126.2 . . ? C21 C22 H22 126.2 . . ? C22 C23 N5 107.48(13) . . ? C22 C23 H23 126.3 . . ? N5 C23 H23 126.3 . . ? N6 C24 C28 121.76(13) . . ? N6 C24 C19 115.31(12) . . ? C28 C24 C19 122.87(12) . . ? N6 C25 C26 123.31(13) . . ? N6 C25 H25 118.3 . . ? C26 C25 H25 118.3 . . ? C27 C26 C25 118.13(14) . . ? C27 C26 H26 120.9 . . ? C25 C26 H26 120.9 . . ? C26 C27 C28 119.19(14) . . ? C26 C27 H27 120.4 . . ? C28 C27 H27 120.4 . . ? C27 C28 C24 119.26(13) . . ? C27 C28 H28 120.4 . . ? C24 C28 H28 120.4 . . ? C1 N1 C4 109.22(11) . . ? C1 N1 H1A 125.4 . . ? C4 N1 H1A 125.4 . . ? C6 N2 C9 110.06(12) . . ? C6 N2 H2A 125.0 . . ? C9 N2 H2A 125.0 . . ? C11 N3 C10 118.09(13) . . ? C15 N4 C18 109.47(12) . . ? C15 N4 H4A 125.3 . . ? C18 N4 H4A 125.3 . . ? C23 N5 C20 110.30(12) . . ? C23 N5 H5A 124.8 . . ? C20 N5 H5A 124.8 . . ? C24 N6 C25 118.33(12) . . ? _diffrn_measured_fraction_theta_max 0.875 _diffrn_reflns_theta_full 28.07 _diffrn_measured_fraction_theta_full 0.875 _refine_diff_density_max 0.326 _refine_diff_density_min -0.244 _refine_diff_density_rms 0.048 #============================================================================== # End of CIF #==============================================================================