# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_han1cult _audit_creation_date 2012-09-19 _audit_creation_method ; Olex2 1.2-beta (compiled May 9 2012 12:37:22, GUI svn.r4230) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C15 H17 N5' _chemical_formula_sum 'C15 H17 N5' _chemical_formula_weight 267.34 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 9.4160(2) _cell_length_b 12.7884(2) _cell_length_c 12.9807(4) _cell_angle_alpha 90.00 _cell_angle_beta 108.879(3) _cell_angle_gamma 90.00 _cell_volume 1478.99(6) _cell_formula_units_Z 4 _cell_measurement_reflns_used 4683 _cell_measurement_temperature 173.00(14) _cell_measurement_theta_max 71.3138 _cell_measurement_theta_min 3.5964 _exptl_absorpt_coefficient_mu 0.602 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.59148 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.201 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 568 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.25 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0177 _diffrn_reflns_av_unetI/netI 0.0179 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 7102 _diffrn_reflns_theta_full 66.50 _diffrn_reflns_theta_max 66.97 _diffrn_reflns_theta_min 4.96 _diffrn_ambient_temperature 173.00(14) _diffrn_detector_area_resol_mean 15.9578 _diffrn_measured_fraction_theta_full 0.9874 _diffrn_measured_fraction_theta_max 0.9974 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 40.00 70.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -25.0000 120.0000 30 #__ type_ start__ end____ width___ exp.time_ 2 omega -9.00 23.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 -77.0000 -90.0000 32 #__ type_ start__ end____ width___ exp.time_ 3 omega -57.00 -21.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 -77.0000 -90.0000 36 #__ type_ start__ end____ width___ exp.time_ 4 omega -112.00 -52.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - -55.0000 125.0000 -60.0000 60 #__ type_ start__ end____ width___ exp.time_ 5 omega 74.00 125.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 55.0000 125.0000 60.0000 51 #__ type_ start__ end____ width___ exp.time_ 6 omega 34.00 119.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 55.0000 57.0000 90.0000 85 #__ type_ start__ end____ width___ exp.time_ 7 omega -4.00 68.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 55.0000 -57.0000 120.0000 72 #__ type_ start__ end____ width___ exp.time_ 8 omega -9.00 70.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 55.0000 -38.0000 -60.0000 79 #__ type_ start__ end____ width___ exp.time_ 9 omega -114.00 -34.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - -64.0000 -77.0000 -120.0000 80 #__ type_ start__ end____ width___ exp.time_ 10 omega 45.00 129.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -92.0000 -30.0000 84 #__ type_ start__ end____ width___ exp.time_ 11 omega 37.00 72.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -25.0000 30.0000 35 #__ type_ start__ end____ width___ exp.time_ 12 omega 40.00 72.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -25.0000 -90.0000 32 #__ type_ start__ end____ width___ exp.time_ 13 omega 39.00 70.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -25.0000 -150.0000 31 #__ type_ start__ end____ width___ exp.time_ 14 omega 43.00 69.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -38.0000 -150.0000 26 #__ type_ start__ end____ width___ exp.time_ 15 omega 37.00 70.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -25.0000 150.0000 33 #__ type_ start__ end____ width___ exp.time_ 16 omega 40.00 72.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -25.0000 60.0000 32 #__ type_ start__ end____ width___ exp.time_ 17 omega 37.00 72.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -25.0000 90.0000 35 #__ type_ start__ end____ width___ exp.time_ 18 omega 37.00 71.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -25.0000 -120.0000 34 #__ type_ start__ end____ width___ exp.time_ 19 omega 37.00 70.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -25.0000 -180.0000 33 #__ type_ start__ end____ width___ exp.time_ 20 omega 44.00 120.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -64.0000 -30.0000 76 #__ type_ start__ end____ width___ exp.time_ 21 omega 40.00 144.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -92.0000 -180.0000 104 #__ type_ start__ end____ width___ exp.time_ 22 omega 38.00 72.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -25.0000 -30.0000 34 #__ type_ start__ end____ width___ exp.time_ 23 omega 38.00 65.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -25.0000 -60.0000 27 ; _diffrn_measurement_device 'kappa diffractometer' _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.1472678000 _diffrn_orient_matrix_UB_12 -0.0582092000 _diffrn_orient_matrix_UB_13 0.0106694000 _diffrn_orient_matrix_UB_21 0.0548460000 _diffrn_orient_matrix_UB_22 0.0202976000 _diffrn_orient_matrix_UB_23 0.1236728000 _diffrn_orient_matrix_UB_31 -0.0721923000 _diffrn_orient_matrix_UB_32 -0.1034962000 _diffrn_orient_matrix_UB_33 0.0182671000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.5418 _diffrn_source 'sealed X-ray tube' _diffrn_source_current 35 _diffrn_source_power 1.75 _diffrn_source_target Cu _diffrn_source_voltage 50 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2406 _reflns_number_total 2584 _reflns_odcompleteness_completeness 98.74 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 68.13 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 0.170 _refine_diff_density_min -0.166 _refine_diff_density_rms 0.029 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 183 _refine_ls_number_reflns 2584 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0379 _refine_ls_R_factor_gt 0.0355 _refine_ls_restrained_S_all 1.003 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0648P)^2^+0.1607P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0999 _refine_ls_wR_factor_ref 0.1027 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.13460(9) 0.41445(6) 0.58527(7) 0.0337(2) Uani 1 1 d . . . N2 N -0.03672(10) 0.25459(7) 0.62555(7) 0.0414(2) Uani 1 1 d . . . H2A H -0.0875 0.1998 0.6396 0.050 Uiso 1 1 d R . . H2B H -0.0205 0.2581 0.5610 0.050 Uiso 1 1 d R . . N3 N 0.18743(11) 0.56638(7) 0.81709(8) 0.0463(2) Uani 1 1 d . . . N4 N -0.03576(12) 0.31766(9) 0.88208(8) 0.0510(3) Uani 1 1 d . . . N5 N 0.36783(11) 0.50866(7) 0.17956(7) 0.0424(2) Uani 1 1 d . . . C1 C 0.09986(11) 0.41364(7) 0.68137(8) 0.0338(2) Uani 1 1 d . . . C2 C 0.01591(11) 0.33206(8) 0.69830(8) 0.0348(2) Uani 1 1 d . . . C3 C 0.14581(11) 0.49636(8) 0.75949(8) 0.0369(3) Uani 1 1 d . . . C4 C -0.01601(11) 0.32559(8) 0.79971(8) 0.0395(3) Uani 1 1 d . . . C5 C 0.33096(11) 0.50393(7) 0.27286(8) 0.0350(2) Uani 1 1 d . . . C6 C 0.24028(12) 0.42205(8) 0.29055(8) 0.0371(2) Uani 1 1 d . . . H6 H 0.2045 0.3697 0.2365 0.045 Uiso 1 1 calc R . . C7 C 0.20304(11) 0.41684(7) 0.38405(8) 0.0347(2) Uani 1 1 d . . . H7 H 0.1423 0.3607 0.3935 0.042 Uiso 1 1 calc R . . C8 C 0.25243(10) 0.49242(7) 0.46616(8) 0.0328(2) Uani 1 1 d . . . C9 C 0.34252(12) 0.57289(8) 0.44900(8) 0.0375(2) Uani 1 1 d . . . H9 H 0.3781 0.6249 0.5035 0.045 Uiso 1 1 calc R . . C10 C 0.38134(12) 0.57923(8) 0.35579(9) 0.0386(2) Uani 1 1 d . . . H10 H 0.4430 0.6352 0.3473 0.046 Uiso 1 1 calc R . . C11 C 0.21333(11) 0.48896(7) 0.56454(8) 0.0343(2) Uani 1 1 d . . . H11 H 0.2469 0.5437 0.6162 0.041 Uiso 1 1 calc R . . C12 C 0.47848(12) 0.58283(9) 0.16687(9) 0.0451(3) Uani 1 1 d . . . H12A H 0.5291 0.5519 0.1181 0.054 Uiso 1 1 calc R . . H12B H 0.5556 0.5941 0.2387 0.054 Uiso 1 1 calc R . . C13 C 0.41314(15) 0.68752(10) 0.12114(11) 0.0574(3) Uani 1 1 d . . . H13A H 0.3392 0.6775 0.0487 0.086 Uiso 1 1 calc R . . H13B H 0.4937 0.7334 0.1155 0.086 Uiso 1 1 calc R . . H13C H 0.3642 0.7194 0.1695 0.086 Uiso 1 1 calc R . . C14 C 0.29728(14) 0.44094(10) 0.08653(9) 0.0510(3) Uani 1 1 d . . . H14A H 0.2946 0.4779 0.0189 0.061 Uiso 1 1 calc R . . H14B H 0.1923 0.4273 0.0830 0.061 Uiso 1 1 calc R . . C15 C 0.37739(19) 0.33749(12) 0.09137(13) 0.0677(4) Uani 1 1 d . . . H15A H 0.3286 0.2976 0.0249 0.102 Uiso 1 1 calc R . . H15B H 0.3729 0.2976 0.1547 0.102 Uiso 1 1 calc R . . H15C H 0.4825 0.3503 0.0976 0.102 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 0.0355(4) 0.0351(4) 0.0304(4) 0.0023(3) 0.0105(3) 0.0041(3) N2 0.0525(5) 0.0378(5) 0.0381(5) 0.0019(3) 0.0207(4) -0.0026(4) N3 0.0497(5) 0.0476(5) 0.0405(5) -0.0065(4) 0.0131(4) 0.0062(4) N4 0.0546(6) 0.0637(6) 0.0392(5) 0.0087(4) 0.0215(4) 0.0089(5) N5 0.0477(5) 0.0459(5) 0.0364(5) 0.0055(4) 0.0176(4) -0.0014(4) C1 0.0347(5) 0.0364(5) 0.0299(5) 0.0027(4) 0.0099(4) 0.0077(4) C2 0.0359(5) 0.0379(5) 0.0313(5) 0.0057(4) 0.0117(4) 0.0093(4) C3 0.0362(5) 0.0422(6) 0.0326(5) 0.0038(4) 0.0117(4) 0.0097(4) C4 0.0390(5) 0.0429(6) 0.0375(6) 0.0072(4) 0.0134(4) 0.0075(4) C5 0.0348(5) 0.0365(5) 0.0330(5) 0.0063(4) 0.0100(4) 0.0046(4) C6 0.0401(5) 0.0367(5) 0.0336(5) -0.0029(4) 0.0105(4) -0.0038(4) C7 0.0353(5) 0.0332(5) 0.0354(5) 0.0014(4) 0.0112(4) -0.0030(4) C8 0.0334(5) 0.0316(5) 0.0311(5) 0.0026(4) 0.0074(4) 0.0024(4) C9 0.0428(5) 0.0322(5) 0.0351(5) -0.0016(4) 0.0094(4) -0.0027(4) C10 0.0405(5) 0.0334(5) 0.0414(6) 0.0043(4) 0.0126(4) -0.0052(4) C11 0.0367(5) 0.0325(5) 0.0314(5) 0.0005(4) 0.0078(4) 0.0025(4) C12 0.0409(6) 0.0531(6) 0.0439(6) 0.0137(5) 0.0174(5) 0.0045(5) C13 0.0531(7) 0.0582(7) 0.0600(8) 0.0242(6) 0.0172(6) 0.0021(6) C14 0.0585(7) 0.0641(7) 0.0316(5) 0.0017(5) 0.0160(5) -0.0034(6) C15 0.0853(10) 0.0640(8) 0.0636(8) -0.0155(7) 0.0378(8) -0.0048(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.3883(12) . ? N1 C11 1.2881(13) . ? N2 C2 1.3477(13) . ? N3 C3 1.1510(14) . ? N4 C4 1.1475(14) . ? N5 C5 1.3649(13) . ? N5 C12 1.4572(14) . ? N5 C14 1.4596(15) . ? C1 C2 1.3690(15) . ? C1 C3 1.4320(14) . ? C2 C4 1.4443(14) . ? C5 C6 1.4160(14) . ? C5 C10 1.4074(14) . ? C6 C7 1.3697(14) . ? C7 C8 1.4021(14) . ? C8 C9 1.3967(14) . ? C8 C11 1.4396(14) . ? C9 C10 1.3748(15) . ? C12 C13 1.5123(16) . ? C14 C15 1.514(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 N1 C1 120.80(8) . . ? C5 N5 C12 121.71(9) . . ? C5 N5 C14 121.97(9) . . ? C12 N5 C14 116.32(9) . . ? N1 C1 C3 121.72(9) . . ? C2 C1 N1 117.78(9) . . ? C2 C1 C3 120.48(9) . . ? N2 C2 C1 123.25(9) . . ? N2 C2 C4 117.31(9) . . ? C1 C2 C4 119.42(9) . . ? N3 C3 C1 174.91(11) . . ? N4 C4 C2 176.92(11) . . ? N5 C5 C6 121.10(9) . . ? N5 C5 C10 121.92(9) . . ? C10 C5 C6 116.98(9) . . ? C7 C6 C5 121.36(9) . . ? C6 C7 C8 121.54(9) . . ? C7 C8 C11 122.41(9) . . ? C9 C8 C7 117.12(9) . . ? C9 C8 C11 120.47(9) . . ? C10 C9 C8 122.14(9) . . ? C9 C10 C5 120.86(9) . . ? N1 C11 C8 122.53(9) . . ? N5 C12 C13 113.93(9) . . ? N5 C14 C15 113.38(10) . . ? 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 N2 -1.51(14) . . . . ? N1 C1 C2 C4 176.83(8) . . . . ? N1 C1 C3 N3 1.2(12) . . . . ? N2 C2 C4 N4 85(2) . . . . ? N5 C5 C6 C7 179.94(9) . . . . ? N5 C5 C10 C9 179.90(9) . . . . ? C1 N1 C11 C8 179.67(8) . . . . ? C1 C2 C4 N4 -93(2) . . . . ? C2 C1 C3 N3 -177.0(11) . . . . ? C3 C1 C2 N2 176.74(9) . . . . ? C3 C1 C2 C4 -4.93(14) . . . . ? C5 N5 C12 C13 -88.99(13) . . . . ? C5 N5 C14 C15 -88.57(13) . . . . ? C5 C6 C7 C8 0.25(16) . . . . ? C6 C5 C10 C9 -0.41(15) . . . . ? C6 C7 C8 C9 -0.56(14) . . . . ? C6 C7 C8 C11 179.36(9) . . . . ? C7 C8 C9 C10 0.40(15) . . . . ? C7 C8 C11 N1 2.35(15) . . . . ? C8 C9 C10 C5 0.09(15) . . . . ? C9 C8 C11 N1 -177.72(9) . . . . ? C10 C5 C6 C7 0.24(15) . . . . ? C11 N1 C1 C2 -179.93(9) . . . . ? C11 N1 C1 C3 1.85(14) . . . . ? C11 C8 C9 C10 -179.53(9) . . . . ? C12 N5 C5 C6 -170.70(9) . . . . ? C12 N5 C5 C10 8.98(15) . . . . ? C12 N5 C14 C15 92.28(12) . . . . ? C14 N5 C5 C6 10.19(15) . . . . ? C14 N5 C5 C10 -170.13(10) . . . . ? C14 N5 C12 C13 90.16(13) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 921366'