# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # 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_tangmeng0320 _audit_creation_date 2013-03-21 _audit_creation_method ; Olex2 1.2 (compiled Dec 5 2012 16:20:19, GUI svn.r4385) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C15 H12 N2' _chemical_formula_sum 'C15 H12 N2' _chemical_formula_weight 220.27 _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 0.0033 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' _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_H-M_alt 'C 1 2/c 1' _space_group_name_Hall '-C 2yc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y, -z+1/2' 3 'x+1/2, y+1/2, z' 4 '-x+1/2, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x, -y, z-1/2' 7 '-x+1/2, -y+1/2, -z' 8 'x+1/2, -y+1/2, z-1/2' _cell_length_a 16.9366(9) _cell_length_b 17.1465(7) _cell_length_c 17.6534(9) _cell_angle_alpha 90.00 _cell_angle_beta 109.578(6) _cell_angle_gamma 90.00 _cell_volume 4830.2(4) _cell_formula_units_Z 16 _cell_measurement_reflns_used 2636 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 23.6850 _cell_measurement_theta_min 3.4800 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.84788 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light yellow' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.212 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1856 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.28 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0286 _diffrn_reflns_av_unetI/netI 0.0469 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 10140 _diffrn_reflns_theta_full 25.50 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 3.34 _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 16.0733 _diffrn_measured_fraction_theta_full 0.9978 _diffrn_measured_fraction_theta_max 0.8893 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 40.00 101.20 1.2000 14.0000 omega____ theta____ kappa____ phi______ frames - 22.6512 178.0000 90.0000 51 #__ type_ start__ end____ width___ exp.time_ 2 omega -39.00 36.60 1.2000 14.0000 omega____ theta____ kappa____ phi______ frames - 22.6512 -38.0000 30.0000 63 #__ type_ start__ end____ width___ exp.time_ 3 omega -11.00 95.80 1.2000 14.0000 omega____ theta____ kappa____ phi______ frames - 22.6512 38.0000 -150.0000 89 ; _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0359713000 _diffrn_orient_matrix_UB_12 0.0228163000 _diffrn_orient_matrix_UB_13 -0.0034978000 _diffrn_orient_matrix_UB_21 -0.0130720000 _diffrn_orient_matrix_UB_22 -0.0280954000 _diffrn_orient_matrix_UB_23 0.0228174000 _diffrn_orient_matrix_UB_31 0.0225581000 _diffrn_orient_matrix_UB_32 0.0200300000 _diffrn_orient_matrix_UB_33 0.0359046000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'SuperNova (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 3152 _reflns_number_total 4927 _reflns_odcompleteness_completeness 99.78 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) ; _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 ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution 'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790' _refine_diff_density_max 0.154 _refine_diff_density_min -0.167 _refine_diff_density_rms 0.036 _refine_ls_extinction_coef 0.0018(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 0.981 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 312 _refine_ls_number_reflns 4927 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0932 _refine_ls_R_factor_gt 0.0552 _refine_ls_restrained_S_all 0.981 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0590P)^2^+2.1388P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1252 _refine_ls_wR_factor_ref 0.1504 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: H1 of N1, H2 of N2, H4 of N4, H20 of C20, H2A of C2, H3A of C3, H4A of C4, H5 of C5, H6 of C6, H8 of C8, H11 of C11, H12 of C12, H13 of C13, H14 of C14, H15 of C15, H17 of C17, H18 of C18, H19 of C19, H21 of C21, H23 of C23, H26 of C26, H27 of C27, H28 of C28, H29 of C29, H30 of C30 2. Restrained distances H3-N3 0.86 with sigma of 0.02 3. Others Fixed Sof: H1(0.5) H2(0.5) H4(0.5) H3(0.5) 4.a Aromatic/amide H refined with riding coordinates: N1(H1), N2(H2), N4(H4), C2(H2A), C3(H3A), C4(H4A), C5(H5), C6(H6), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _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 0.09060(10) 0.74025(9) 0.27710(10) 0.0476(4) Uani 1 1 d . . . H1 H 0.0378 0.7492 0.2648 0.057 Uiso 0.50 1 calc PR . . N2 N 0.12591(10) 0.69143(9) 0.23769(9) 0.0476(4) Uani 1 1 d . . . H2 H 0.0993 0.6641 0.1961 0.057 Uiso 0.50 1 calc PR . . N3 N 0.96413(11) 0.44736(10) 0.66208(10) 0.0523(5) Uani 1 1 d D . . N4 N 0.99933(11) 0.39746(10) 0.62389(9) 0.0527(4) Uani 1 1 d . . . H4 H 1.0403 0.3665 0.6468 0.063 Uiso 0.50 1 calc PR . . C1 C 0.13234(13) 0.82988(11) 0.39169(12) 0.0477(5) Uani 1 1 d . . . C2 C 0.05150(16) 0.85838(13) 0.37624(14) 0.0649(6) Uani 1 1 d . . . H2A H 0.0084 0.8405 0.3314 0.078 Uiso 1 1 calc R . . C3 C 0.03436(19) 0.91215(15) 0.42581(18) 0.0837(8) Uani 1 1 d . . . H3A H -0.0200 0.9306 0.4146 0.100 Uiso 1 1 calc R . . C4 C 0.0978(2) 0.93903(16) 0.49241(18) 0.0866(9) Uani 1 1 d . . . H4A H 0.0863 0.9759 0.5260 0.104 Uiso 1 1 calc R . . C5 C 0.1776(2) 0.91140(15) 0.50904(16) 0.0810(8) Uani 1 1 d . . . H5 H 0.2202 0.9293 0.5541 0.097 Uiso 1 1 calc R . . C6 C 0.19493(16) 0.85707(13) 0.45921(13) 0.0648(6) Uani 1 1 d . . . H6 H 0.2493 0.8385 0.4711 0.078 Uiso 1 1 calc R . . C7 C 0.15151(12) 0.77264(11) 0.33877(11) 0.0431(5) Uani 1 1 d . . . C8 C 0.22748(12) 0.74361(11) 0.33826(12) 0.0489(5) Uani 1 1 d . . . H8 H 0.2803 0.7560 0.3740 0.059 Uiso 1 1 calc R . . C9 C 0.20955(11) 0.69239(11) 0.27406(11) 0.0431(5) Uani 1 1 d . . . C10 C 0.26514(13) 0.64496(12) 0.24451(13) 0.0499(5) Uani 1 1 d . . . C11 C 0.23971(16) 0.61424(15) 0.16773(15) 0.0751(7) Uani 1 1 d . . . H11 H 0.1861 0.6249 0.1325 0.090 Uiso 1 1 calc R . . C12 C 0.29258(18) 0.56828(18) 0.14292(19) 0.0920(9) Uani 1 1 d . . . H12 H 0.2745 0.5485 0.0908 0.110 Uiso 1 1 calc R . . C13 C 0.37145(18) 0.55098(17) 0.1935(2) 0.0895(9) Uani 1 1 d . . . H13 H 0.4066 0.5189 0.1767 0.107 Uiso 1 1 calc R . . C14 C 0.39756(17) 0.58179(18) 0.26921(19) 0.0898(9) Uani 1 1 d . . . H14 H 0.4512 0.5708 0.3040 0.108 Uiso 1 1 calc R . . C15 C 0.34555(14) 0.62906(15) 0.29497(15) 0.0693(7) Uani 1 1 d . . . H15 H 0.3647 0.6502 0.3464 0.083 Uiso 1 1 calc R . . C16 C 0.84799(13) 0.54214(12) 0.62923(12) 0.0513(5) Uani 1 1 d . . . C17 C 0.81699(17) 0.60642(14) 0.58125(15) 0.0743(7) Uani 1 1 d . . . H17 H 0.8339 0.6163 0.5372 0.089 Uiso 1 1 calc R . . C18 C 0.7611(2) 0.65596(17) 0.5984(2) 0.0985(10) Uani 1 1 d . . . H18 H 0.7405 0.6991 0.5658 0.118 Uiso 1 1 calc R . . C19 C 0.7354(2) 0.64235(19) 0.6630(2) 0.0948(10) Uani 1 1 d . . . H19 H 0.6970 0.6755 0.6737 0.114 Uiso 1 1 calc R . . C20 C 0.76670(18) 0.57961(18) 0.71174(18) 0.0845(8) Uani 1 1 d . . . H20 H 0.7500 0.5704 0.7560 0.101 Uiso 1 1 calc R . . C21 C 0.82308(15) 0.52999(14) 0.69519(14) 0.0650(6) Uani 1 1 d . . . H21 H 0.8446 0.4878 0.7289 0.078 Uiso 1 1 calc R . . C22 C 0.90243(12) 0.48643(11) 0.60717(11) 0.0465(5) Uani 1 1 d . . . C23 C 0.89926(13) 0.46077(12) 0.53166(11) 0.0510(5) Uani 1 1 d . . . H23 H 0.8633 0.4784 0.4824 0.061 Uiso 1 1 calc R . . C24 C 0.96010(12) 0.40385(11) 0.54409(11) 0.0462(5) Uani 1 1 d . . . C25 C 0.98048(13) 0.35383(12) 0.48566(12) 0.0502(5) Uani 1 1 d . . . C26 C 0.95190(15) 0.37263(14) 0.40456(13) 0.0627(6) Uani 1 1 d . . . H26 H 0.9207 0.4179 0.3876 0.075 Uiso 1 1 calc R . . C27 C 0.96875(17) 0.32579(16) 0.34866(15) 0.0757(7) Uani 1 1 d . . . H27 H 0.9483 0.3392 0.2945 0.091 Uiso 1 1 calc R . . C28 C 1.01567(18) 0.25933(17) 0.37245(16) 0.0807(8) Uani 1 1 d . . . H28 H 1.0282 0.2283 0.3348 0.097 Uiso 1 1 calc R . . C29 C 1.04389(19) 0.23895(15) 0.45222(17) 0.0825(8) Uani 1 1 d . . . H29 H 1.0751 0.1936 0.4686 0.099 Uiso 1 1 calc R . . C30 C 1.02622(16) 0.28547(14) 0.50833(14) 0.0692(7) Uani 1 1 d . . . H30 H 1.0453 0.2708 0.5621 0.083 Uiso 1 1 calc R . . H3 H 0.983(2) 0.4542(19) 0.7133(11) 0.035(10) Uiso 0.50 1 d PD . . 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 0.0370(9) 0.0540(10) 0.0489(9) -0.0076(8) 0.0107(8) -0.0028(8) N2 0.0356(9) 0.0572(10) 0.0465(9) -0.0086(8) 0.0092(7) -0.0043(8) N3 0.0496(11) 0.0615(11) 0.0394(10) 0.0042(9) 0.0064(9) 0.0018(9) N4 0.0502(10) 0.0623(11) 0.0397(9) 0.0080(8) 0.0070(8) 0.0055(9) C1 0.0504(12) 0.0466(11) 0.0486(12) -0.0043(9) 0.0201(10) -0.0073(10) C2 0.0590(15) 0.0696(15) 0.0664(15) -0.0145(12) 0.0214(12) 0.0020(12) C3 0.082(2) 0.0825(18) 0.095(2) -0.0201(16) 0.0411(17) 0.0105(16) C4 0.114(3) 0.0751(17) 0.087(2) -0.0270(15) 0.055(2) -0.0007(18) C5 0.092(2) 0.0856(18) 0.0681(16) -0.0334(14) 0.0305(15) -0.0209(17) C6 0.0612(15) 0.0734(15) 0.0597(14) -0.0197(12) 0.0199(12) -0.0130(12) C7 0.0392(11) 0.0465(11) 0.0414(10) -0.0026(9) 0.0107(9) -0.0081(9) C8 0.0339(10) 0.0597(12) 0.0467(11) -0.0071(10) 0.0048(9) -0.0071(9) C9 0.0332(10) 0.0490(11) 0.0449(11) -0.0015(9) 0.0101(8) -0.0061(9) C10 0.0395(11) 0.0548(12) 0.0565(12) -0.0080(10) 0.0175(10) -0.0065(9) C11 0.0503(14) 0.0978(19) 0.0726(16) -0.0303(15) 0.0145(12) 0.0024(13) C12 0.0640(18) 0.114(2) 0.102(2) -0.0519(18) 0.0325(16) -0.0079(16) C13 0.0618(18) 0.092(2) 0.125(3) -0.0365(19) 0.0455(18) -0.0005(15) C14 0.0464(15) 0.118(2) 0.104(2) -0.0143(19) 0.0249(15) 0.0151(15) C15 0.0431(13) 0.0954(18) 0.0662(15) -0.0122(13) 0.0142(11) 0.0028(13) C16 0.0470(12) 0.0522(12) 0.0478(12) -0.0051(10) 0.0070(10) -0.0030(10) C17 0.0786(18) 0.0683(15) 0.0727(16) 0.0115(13) 0.0210(14) 0.0161(14) C18 0.106(3) 0.0792(19) 0.103(2) 0.0062(17) 0.026(2) 0.0369(18) C19 0.086(2) 0.092(2) 0.102(2) -0.0289(19) 0.0254(19) 0.0217(18) C20 0.080(2) 0.097(2) 0.0819(19) -0.0239(17) 0.0345(16) 0.0031(17) C21 0.0654(15) 0.0687(15) 0.0589(14) -0.0055(12) 0.0184(12) -0.0017(12) C22 0.0411(11) 0.0504(11) 0.0419(11) 0.0063(9) 0.0057(9) -0.0019(9) C23 0.0457(12) 0.0628(13) 0.0359(11) 0.0085(10) 0.0021(9) 0.0047(10) C24 0.0415(11) 0.0536(12) 0.0381(10) 0.0054(9) 0.0061(9) -0.0015(10) C25 0.0451(12) 0.0576(12) 0.0440(11) 0.0025(10) 0.0099(9) -0.0033(10) C26 0.0618(15) 0.0763(15) 0.0477(13) 0.0031(11) 0.0155(11) 0.0069(12) C27 0.0809(18) 0.0943(19) 0.0516(14) -0.0049(14) 0.0216(13) 0.0018(16) C28 0.089(2) 0.0839(19) 0.0715(18) -0.0197(15) 0.0303(16) -0.0011(16) C29 0.098(2) 0.0662(16) 0.0830(19) -0.0036(14) 0.0307(17) 0.0179(15) C30 0.0803(18) 0.0673(15) 0.0557(14) 0.0063(12) 0.0171(13) 0.0099(14) _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 H1 0.8600 . ? N1 N2 1.350(2) . ? N1 C7 1.344(2) . ? N2 H2 0.8600 . ? N2 C9 1.345(2) . ? N3 N4 1.346(2) . ? N3 C22 1.342(2) . ? N3 H3 0.861(17) . ? N4 H4 0.8600 . ? N4 C24 1.346(2) . ? C1 C2 1.392(3) . ? C1 C6 1.384(3) . ? C1 C7 1.464(3) . ? C2 H2A 0.9300 . ? C2 C3 1.368(3) . ? C3 H3A 0.9300 . ? C3 C4 1.379(4) . ? C4 H4A 0.9300 . ? C4 C5 1.368(4) . ? C5 H5 0.9300 . ? C5 C6 1.379(3) . ? C6 H6 0.9300 . ? C7 C8 1.382(3) . ? C8 H8 0.9300 . ? C8 C9 1.385(3) . ? C9 C10 1.466(3) . ? C10 C11 1.382(3) . ? C10 C15 1.382(3) . ? C11 H11 0.9300 . ? C11 C12 1.370(3) . ? C12 H12 0.9300 . ? C12 C13 1.368(4) . ? C13 H13 0.9300 . ? C13 C14 1.365(4) . ? C14 H14 0.9300 . ? C14 C15 1.381(3) . ? C15 H15 0.9300 . ? C16 C17 1.382(3) . ? C16 C21 1.381(3) . ? C16 C22 1.468(3) . ? C17 H17 0.9300 . ? C17 C18 1.380(4) . ? C18 H18 0.9300 . ? C18 C19 1.370(4) . ? C19 H19 0.9300 . ? C19 C20 1.368(4) . ? C20 H20 0.9300 . ? C20 C21 1.381(3) . ? C21 H21 0.9300 . ? C22 C23 1.387(3) . ? C23 H23 0.9300 . ? C23 C24 1.382(3) . ? C24 C25 1.469(3) . ? C25 C26 1.387(3) . ? C25 C30 1.388(3) . ? C26 H26 0.9300 . ? C26 C27 1.374(3) . ? C27 H27 0.9300 . ? C27 C28 1.372(4) . ? C28 H28 0.9300 . ? C28 C29 1.372(3) . ? C29 H29 0.9300 . ? C29 C30 1.380(3) . ? C30 H30 0.9300 . ? 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 N2 N1 H1 125.6 . . ? C7 N1 H1 125.6 . . ? C7 N1 N2 108.76(16) . . ? N1 N2 H2 125.5 . . ? N1 N2 C9 108.91(15) . . ? C9 N2 H2 125.5 . . ? N4 N3 C22 108.90(16) . . ? N4 N3 H3 122(2) . . ? C22 N3 H3 128(2) . . ? N3 N4 H4 125.5 . . ? N3 N4 C24 109.05(16) . . ? C24 N4 H4 125.5 . . ? C2 C1 C7 121.61(19) . . ? C6 C1 C2 118.0(2) . . ? C6 C1 C7 120.37(19) . . ? C1 C2 H2A 119.4 . . ? C3 C2 C1 121.1(2) . . ? C3 C2 H2A 119.4 . . ? C2 C3 H3A 120.0 . . ? C2 C3 C4 120.0(3) . . ? C4 C3 H3A 120.0 . . ? C3 C4 H4A 120.1 . . ? C5 C4 C3 119.9(2) . . ? C5 C4 H4A 120.1 . . ? C4 C5 H5 119.9 . . ? C4 C5 C6 120.3(3) . . ? C6 C5 H5 119.9 . . ? C1 C6 H6 119.6 . . ? C5 C6 C1 120.8(2) . . ? C5 C6 H6 119.6 . . ? N1 C7 C1 121.31(18) . . ? N1 C7 C8 108.03(16) . . ? C8 C7 C1 130.64(18) . . ? C7 C8 H8 126.7 . . ? C7 C8 C9 106.52(17) . . ? C9 C8 H8 126.7 . . ? N2 C9 C8 107.78(17) . . ? N2 C9 C10 121.51(17) . . ? C8 C9 C10 130.71(18) . . ? C11 C10 C9 122.3(2) . . ? C11 C10 C15 118.2(2) . . ? C15 C10 C9 119.47(19) . . ? C10 C11 H11 119.6 . . ? C12 C11 C10 120.7(2) . . ? C12 C11 H11 119.6 . . ? C11 C12 H12 119.5 . . ? C13 C12 C11 121.1(3) . . ? C13 C12 H12 119.5 . . ? C12 C13 H13 120.6 . . ? C14 C13 C12 118.7(2) . . ? C14 C13 H13 120.6 . . ? C13 C14 H14 119.5 . . ? C13 C14 C15 121.1(3) . . ? C15 C14 H14 119.5 . . ? C10 C15 C14 120.2(2) . . ? C10 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C17 C16 C22 120.0(2) . . ? C21 C16 C17 118.5(2) . . ? C21 C16 C22 121.5(2) . . ? C16 C17 H17 119.9 . . ? C18 C17 C16 120.3(3) . . ? C18 C17 H17 119.9 . . ? C17 C18 H18 119.6 . . ? C19 C18 C17 120.7(3) . . ? C19 C18 H18 119.6 . . ? C18 C19 H19 120.2 . . ? C18 C19 C20 119.5(3) . . ? C20 C19 H19 120.2 . . ? C19 C20 H20 120.0 . . ? C19 C20 C21 120.1(3) . . ? C21 C20 H20 120.0 . . ? C16 C21 H21 119.5 . . ? C20 C21 C16 120.9(2) . . ? C20 C21 H21 119.5 . . ? N3 C22 C16 122.64(18) . . ? N3 C22 C23 107.80(18) . . ? C23 C22 C16 129.47(18) . . ? C22 C23 H23 126.7 . . ? C24 C23 C22 106.54(17) . . ? C24 C23 H23 126.7 . . ? N4 C24 C23 107.70(17) . . ? N4 C24 C25 122.54(18) . . ? C23 C24 C25 129.71(18) . . ? C26 C25 C24 120.42(19) . . ? C26 C25 C30 117.5(2) . . ? C30 C25 C24 122.04(18) . . ? C25 C26 H26 119.3 . . ? C27 C26 C25 121.4(2) . . ? C27 C26 H26 119.3 . . ? C26 C27 H27 119.9 . . ? C28 C27 C26 120.3(2) . . ? C28 C27 H27 119.9 . . ? C27 C28 H28 120.2 . . ? C29 C28 C27 119.5(2) . . ? C29 C28 H28 120.2 . . ? C28 C29 H29 119.9 . . ? C28 C29 C30 120.3(2) . . ? C30 C29 H29 119.9 . . ? C25 C30 H30 119.5 . . ? C29 C30 C25 121.0(2) . . ? C29 C30 H30 119.5 . . ? 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 N2 C9 C8 -0.2(2) . . . . ? N1 N2 C9 C10 -179.87(17) . . . . ? N1 C7 C8 C9 -0.2(2) . . . . ? N2 N1 C7 C1 178.60(16) . . . . ? N2 N1 C7 C8 0.1(2) . . . . ? N2 C9 C10 C11 18.3(3) . . . . ? N2 C9 C10 C15 -160.8(2) . . . . ? N3 N4 C24 C23 1.2(2) . . . . ? N3 N4 C24 C25 -176.33(17) . . . . ? N3 C22 C23 C24 1.3(2) . . . . ? N4 N3 C22 C16 176.19(18) . . . . ? N4 N3 C22 C23 -0.6(2) . . . . ? N4 C24 C25 C26 -166.3(2) . . . . ? N4 C24 C25 C30 15.7(3) . . . . ? C1 C2 C3 C4 0.0(4) . . . . ? C1 C7 C8 C9 -178.51(19) . . . . ? C2 C1 C6 C5 -0.7(3) . . . . ? C2 C1 C7 N1 -5.9(3) . . . . ? C2 C1 C7 C8 172.2(2) . . . . ? C2 C3 C4 C5 -0.5(4) . . . . ? C3 C4 C5 C6 0.4(4) . . . . ? C4 C5 C6 C1 0.2(4) . . . . ? C6 C1 C2 C3 0.6(3) . . . . ? C6 C1 C7 N1 173.93(19) . . . . ? C6 C1 C7 C8 -8.0(3) . . . . ? C7 N1 N2 C9 0.0(2) . . . . ? C7 C1 C2 C3 -179.6(2) . . . . ? C7 C1 C6 C5 179.5(2) . . . . ? C7 C8 C9 N2 0.2(2) . . . . ? C7 C8 C9 C10 179.90(19) . . . . ? C8 C9 C10 C11 -161.3(2) . . . . ? C8 C9 C10 C15 19.6(3) . . . . ? C9 C10 C11 C12 -178.1(2) . . . . ? C9 C10 C15 C14 177.3(2) . . . . ? C10 C11 C12 C13 0.6(5) . . . . ? C11 C10 C15 C14 -1.8(4) . . . . ? C11 C12 C13 C14 -1.4(5) . . . . ? C12 C13 C14 C15 0.5(5) . . . . ? C13 C14 C15 C10 1.1(4) . . . . ? C15 C10 C11 C12 1.0(4) . . . . ? C16 C17 C18 C19 0.0(5) . . . . ? C16 C22 C23 C24 -175.2(2) . . . . ? C17 C16 C21 C20 1.8(4) . . . . ? C17 C16 C22 N3 147.5(2) . . . . ? C17 C16 C22 C23 -36.4(3) . . . . ? C17 C18 C19 C20 1.1(5) . . . . ? C18 C19 C20 C21 -0.7(5) . . . . ? C19 C20 C21 C16 -0.7(4) . . . . ? C21 C16 C17 C18 -1.4(4) . . . . ? C21 C16 C22 N3 -35.9(3) . . . . ? C21 C16 C22 C23 140.2(2) . . . . ? C22 N3 N4 C24 -0.3(2) . . . . ? C22 C16 C17 C18 175.4(2) . . . . ? C22 C16 C21 C20 -174.9(2) . . . . ? C22 C23 C24 N4 -1.5(2) . . . . ? C22 C23 C24 C25 175.75(19) . . . . ? C23 C24 C25 C26 16.7(3) . . . . ? C23 C24 C25 C30 -161.2(2) . . . . ? C24 C25 C26 C27 -178.6(2) . . . . ? C24 C25 C30 C29 179.3(2) . . . . ? C25 C26 C27 C28 -0.9(4) . . . . ? C26 C25 C30 C29 1.3(4) . . . . ? C26 C27 C28 C29 1.6(4) . . . . ? C27 C28 C29 C30 -0.9(4) . . . . ? C28 C29 C30 C25 -0.6(4) . . . . ? C30 C25 C26 C27 -0.6(3) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 939872'