# Electronic Supplementary Material (ESI) for Chemical Science # 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_zhiy1cult #TrackingRef '18348_web_deposit_cif_file_0_ZhiyongYANG_1362623376.zhiy1cult.cif' _audit_creation_date 2011-11-22 _audit_creation_method ; Olex2 1.1-beta (compiled Nov 1 2011 20:42:30, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C31 H22 N2' _chemical_formula_sum 'C31 H22 N2' _chemical_formula_weight 422.51 _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 Orthorhombic _symmetry_space_group_name_H-M Pbca _space_group_IT_number 61 _space_group_name_Hall '-P 2ac 2ab' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z+1/2' 3 'x+1/2, -y+1/2, -z' 4 '-x, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x-1/2, y, -z-1/2' 7 '-x-1/2, y-1/2, z' 8 'x, -y-1/2, z-1/2' _cell_length_a 9.72420(10) _cell_length_b 17.6641(2) _cell_length_c 25.6425(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4404.59(8) _cell_formula_units_Z 8 _cell_measurement_reflns_used 11975 _cell_measurement_temperature 173.00(14) _cell_measurement_theta_max 71.4716 _cell_measurement_theta_min 4.2573 _exptl_absorpt_coefficient_mu 0.572 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.85877 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.274 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 1776 _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.04 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0286 _diffrn_reflns_av_unetI/netI 0.0163 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_number 25386 _diffrn_reflns_theta_full 66.50 _diffrn_reflns_theta_max 67.50 _diffrn_reflns_theta_min 5.01 _diffrn_ambient_temperature 173.00(14) _diffrn_detector_area_resol_mean 15.9578 _diffrn_measured_fraction_theta_full 0.984 _diffrn_measured_fraction_theta_max 0.984 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 38.00 63.90 0.7000 10.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -92.0000 0.0000 37 #__ type_ start__ end____ width___ exp.time_ 2 omega 45.00 72.30 0.7000 10.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -38.0000 90.0000 39 #__ type_ start__ end____ width___ exp.time_ 3 omega 21.00 69.30 0.7000 3.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 57.0000 60.0000 69 #__ type_ start__ end____ width___ exp.time_ 4 omega -21.00 17.50 0.7000 3.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 57.0000 60.0000 55 #__ type_ start__ end____ width___ exp.time_ 5 omega -14.00 75.60 0.7000 3.0000 omega____ theta____ kappa____ phi______ frames - 55.0000 -57.0000 -60.0000 128 #__ type_ start__ end____ width___ exp.time_ 6 omega 79.00 125.20 0.7000 3.0000 omega____ theta____ kappa____ phi______ frames - 55.0000 105.0000 -57.0000 66 #__ type_ start__ end____ width___ exp.time_ 7 omega -3.00 92.90 0.7000 3.0000 omega____ theta____ kappa____ phi______ frames - 55.0000 -125.0000 -90.0000 137 #__ type_ start__ end____ width___ exp.time_ 8 omega 62.00 124.30 0.7000 3.0000 omega____ theta____ kappa____ phi______ frames - 55.0000 57.0000 -90.0000 89 #__ type_ start__ end____ width___ exp.time_ 9 omega -71.00 -5.90 0.7000 10.0000 omega____ theta____ kappa____ phi______ frames - -64.0000 38.0000 120.0000 93 #__ type_ start__ end____ width___ exp.time_ 10 omega -139.00 -52.90 0.7000 10.0000 omega____ theta____ kappa____ phi______ frames - -64.0000 178.0000 30.0000 123 #__ type_ start__ end____ width___ exp.time_ 11 omega 38.00 122.00 0.7000 10.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -92.0000 -90.0000 120 #__ type_ start__ end____ width___ exp.time_ 12 omega 38.00 72.30 0.7000 10.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -38.0000 -180.0000 49 #__ type_ start__ end____ width___ exp.time_ 13 omega 40.00 70.80 0.7000 10.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -38.0000 120.0000 44 #__ type_ start__ end____ width___ exp.time_ 14 omega 84.00 119.00 0.7000 10.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -92.0000 0.0000 50 #__ type_ start__ end____ width___ exp.time_ 15 omega 40.00 82.70 0.7000 10.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -50.0000 -90.0000 61 #__ type_ start__ end____ width___ exp.time_ 16 omega 39.00 71.20 0.7000 10.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -25.0000 60.0000 46 #__ type_ start__ end____ width___ exp.time_ 17 omega 42.00 76.30 0.7000 10.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -111.0000 90.0000 49 #__ type_ start__ end____ width___ exp.time_ 18 omega 89.00 177.90 0.7000 10.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 25.0000 -30.0000 127 #__ type_ start__ end____ width___ exp.time_ 19 omega 38.00 70.20 0.7000 10.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -38.0000 150.0000 46 #__ type_ start__ end____ width___ exp.time_ 20 omega 41.00 79.50 0.7000 10.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -50.0000 -30.0000 55 #__ type_ start__ end____ width___ exp.time_ 21 omega 37.00 71.30 0.7000 10.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -25.0000 30.0000 49 #__ type_ start__ end____ width___ exp.time_ 22 omega 91.00 178.50 0.7000 10.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 50.0000 60.0000 125 #__ type_ start__ end____ width___ exp.time_ 23 omega 59.00 153.50 0.7000 10.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 12.0000 60.0000 135 #__ type_ start__ end____ width___ exp.time_ 24 omega 43.00 137.50 0.7000 10.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -93.0000 117.0000 135 ; _diffrn_measurement_device 'kappa diffractometer' _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0866878000 _diffrn_orient_matrix_UB_12 -0.0683604000 _diffrn_orient_matrix_UB_13 -0.0176036000 _diffrn_orient_matrix_UB_21 0.0613240000 _diffrn_orient_matrix_UB_22 -0.0064344000 _diffrn_orient_matrix_UB_23 0.0552077000 _diffrn_orient_matrix_UB_31 -0.1175410000 _diffrn_orient_matrix_UB_32 -0.0537988000 _diffrn_orient_matrix_UB_33 0.0158597000 _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 30 _diffrn_source_power 1.50 _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 3536 _reflns_number_total 3908 _reflns_odcompleteness_completeness 99.67 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 68.13 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _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 ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.134 _refine_diff_density_min -0.178 _refine_diff_density_rms 0.029 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 298 _refine_ls_number_reflns 3908 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0355 _refine_ls_R_factor_gt 0.0320 _refine_ls_restrained_S_all 1.029 _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^)+(0.0485P)^2^+0.7246P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0835 _refine_ls_wR_factor_ref 0.0865 _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 0.83631(9) 0.63499(5) 0.12804(3) 0.0335(2) Uani 1 1 d . . . C2 C 0.94781(11) 0.64074(6) 0.16244(4) 0.0333(2) Uani 1 1 d . . . C3 C 0.97940(12) 0.59758(7) 0.20643(4) 0.0392(3) Uani 1 1 d . . . H3 H 0.9190 0.5592 0.2187 0.047 Uiso 1 1 calc R . . C4 C 1.10237(13) 0.61303(8) 0.23151(5) 0.0446(3) Uani 1 1 d . . . H4 H 1.1268 0.5841 0.2613 0.054 Uiso 1 1 calc R . . C5 C 1.19147(13) 0.66966(8) 0.21438(5) 0.0448(3) Uani 1 1 d . . . H5 H 1.2754 0.6783 0.2324 0.054 Uiso 1 1 calc R . . C6 C 1.15886(12) 0.71330(7) 0.17149(5) 0.0403(3) Uani 1 1 d . . . H6 H 1.2189 0.7524 0.1601 0.048 Uiso 1 1 calc R . . C7 C 1.03559(11) 0.69896(6) 0.14509(4) 0.0341(2) Uani 1 1 d . . . C8 C 0.97502(11) 0.73027(6) 0.09851(4) 0.0337(2) Uani 1 1 d . . . C9 C 1.01586(12) 0.78709(6) 0.06396(5) 0.0397(3) Uani 1 1 d . . . H9 H 1.0967 0.8158 0.0704 0.048 Uiso 1 1 calc R . . C10 C 0.93707(13) 0.80087(7) 0.02042(5) 0.0432(3) Uani 1 1 d . . . H10 H 0.9632 0.8399 -0.0031 0.052 Uiso 1 1 calc R . . C11 C 0.81911(12) 0.75812(7) 0.01038(5) 0.0416(3) Uani 1 1 d . . . H11 H 0.7673 0.7681 -0.0203 0.050 Uiso 1 1 calc R . . C12 C 0.77605(12) 0.70168(6) 0.04398(4) 0.0368(2) Uani 1 1 d . . . H12 H 0.6961 0.6726 0.0369 0.044 Uiso 1 1 calc R . . C13 C 0.85415(11) 0.68908(6) 0.08866(4) 0.0321(2) Uani 1 1 d . . . C14 C 0.72027(11) 0.58673(6) 0.13337(4) 0.0315(2) Uani 1 1 d . . . C15 C 0.73653(11) 0.51013(6) 0.14444(4) 0.0332(2) Uani 1 1 d . . . H15 H 0.8261 0.4890 0.1472 0.040 Uiso 1 1 calc R . . C16 C 0.62175(11) 0.46484(6) 0.15135(4) 0.0340(2) Uani 1 1 d . . . H16 H 0.6337 0.4130 0.1601 0.041 Uiso 1 1 calc R . . C17 C 0.48865(11) 0.49369(6) 0.14581(4) 0.0324(2) Uani 1 1 d . . . C18 C 0.47454(11) 0.57062(6) 0.13398(4) 0.0335(2) Uani 1 1 d . . . H18 H 0.3852 0.5916 0.1299 0.040 Uiso 1 1 calc R . . C19 C 0.58832(11) 0.61659(6) 0.12819(4) 0.0337(2) Uani 1 1 d . . . H19 H 0.5766 0.6688 0.1206 0.040 Uiso 1 1 calc R . . C20 C 0.36824(11) 0.44532(6) 0.15554(4) 0.0339(2) Uani 1 1 d . . . H20 H 0.3768 0.4100 0.1833 0.041 Uiso 1 1 calc R . . C21 C 0.24766(11) 0.44509(6) 0.12997(4) 0.0306(2) Uani 1 1 d . . . C22 C 0.22807(10) 0.48667(6) 0.07973(4) 0.0293(2) Uani 1 1 d . . . C23 C 0.11706(11) 0.53452(6) 0.07117(4) 0.0352(2) Uani 1 1 d . . . H23 H 0.0517 0.5433 0.0981 0.042 Uiso 1 1 calc R . . C24 C 0.10232(12) 0.56942(7) 0.02312(5) 0.0391(3) Uani 1 1 d . . . H24 H 0.0266 0.6027 0.0185 0.047 Uiso 1 1 calc R . . N25 N 0.18739(10) 0.55933(5) -0.01704(4) 0.0403(2) Uani 1 1 d . . . C26 C 0.29377(12) 0.51279(7) -0.00858(4) 0.0372(2) Uani 1 1 d . . . H26 H 0.3561 0.5042 -0.0365 0.045 Uiso 1 1 calc R . . C27 C 0.31843(11) 0.47649(6) 0.03825(4) 0.0337(2) Uani 1 1 d . . . H27 H 0.3967 0.4448 0.0421 0.040 Uiso 1 1 calc R . . C28 C 0.12905(11) 0.39946(6) 0.14914(4) 0.0315(2) Uani 1 1 d . . . C29 C 0.11546(12) 0.38091(7) 0.20201(4) 0.0400(3) Uani 1 1 d . . . H29 H 0.1809 0.3993 0.2264 0.048 Uiso 1 1 calc R . . C30 C 0.00773(14) 0.33604(7) 0.21907(5) 0.0464(3) Uani 1 1 d . . . H30 H 0.0020 0.3223 0.2548 0.056 Uiso 1 1 calc R . . C31 C -0.09144(14) 0.31100(7) 0.18463(5) 0.0466(3) Uani 1 1 d . . . H31 H -0.1658 0.2808 0.1966 0.056 Uiso 1 1 calc R . . C32 C -0.08146(13) 0.33034(7) 0.13267(5) 0.0450(3) Uani 1 1 d . . . H32 H -0.1503 0.3141 0.1089 0.054 Uiso 1 1 calc R . . C33 C 0.02831(12) 0.37330(6) 0.11496(5) 0.0373(2) Uani 1 1 d . . . H33 H 0.0350 0.3851 0.0789 0.045 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 0.0305(5) 0.0386(5) 0.0315(5) 0.0010(4) -0.0008(4) -0.0023(4) C2 0.0310(5) 0.0395(6) 0.0294(5) -0.0067(4) 0.0010(4) 0.0017(4) C3 0.0379(6) 0.0496(7) 0.0302(5) -0.0018(5) 0.0013(4) 0.0003(5) C4 0.0442(7) 0.0587(8) 0.0310(6) -0.0036(5) -0.0042(5) 0.0057(6) C5 0.0374(6) 0.0567(7) 0.0402(6) -0.0115(5) -0.0080(5) 0.0024(5) C6 0.0341(6) 0.0422(6) 0.0447(6) -0.0115(5) -0.0018(5) -0.0010(5) C7 0.0321(5) 0.0355(5) 0.0347(5) -0.0081(4) 0.0010(4) 0.0016(4) C8 0.0310(5) 0.0323(5) 0.0377(6) -0.0054(4) 0.0025(4) 0.0021(4) C9 0.0355(6) 0.0344(6) 0.0490(7) -0.0009(5) 0.0023(5) -0.0019(4) C10 0.0423(6) 0.0384(6) 0.0488(7) 0.0084(5) 0.0048(5) 0.0003(5) C11 0.0402(6) 0.0441(6) 0.0406(6) 0.0053(5) -0.0018(5) 0.0033(5) C12 0.0333(6) 0.0390(6) 0.0380(6) 0.0004(5) -0.0015(4) -0.0005(4) C13 0.0307(5) 0.0328(5) 0.0327(5) -0.0015(4) 0.0032(4) 0.0023(4) C14 0.0309(5) 0.0385(6) 0.0251(5) -0.0016(4) 0.0012(4) -0.0023(4) C15 0.0295(5) 0.0401(6) 0.0300(5) 0.0007(4) -0.0001(4) 0.0034(4) C16 0.0362(6) 0.0358(6) 0.0301(5) 0.0039(4) 0.0001(4) 0.0017(4) C17 0.0327(5) 0.0391(6) 0.0255(5) 0.0006(4) -0.0009(4) -0.0012(4) C18 0.0294(5) 0.0383(6) 0.0328(5) -0.0020(4) -0.0015(4) 0.0023(4) C19 0.0348(6) 0.0336(5) 0.0328(5) -0.0014(4) 0.0002(4) 0.0011(4) C20 0.0351(6) 0.0365(6) 0.0301(5) 0.0043(4) 0.0010(4) -0.0002(4) C21 0.0323(5) 0.0300(5) 0.0296(5) -0.0014(4) 0.0035(4) 0.0008(4) C22 0.0305(5) 0.0285(5) 0.0289(5) -0.0024(4) 0.0006(4) -0.0034(4) C23 0.0354(6) 0.0352(6) 0.0349(6) -0.0014(4) 0.0047(4) 0.0030(4) C24 0.0389(6) 0.0370(6) 0.0415(6) 0.0036(5) -0.0019(5) 0.0056(5) N25 0.0435(5) 0.0419(5) 0.0355(5) 0.0049(4) -0.0022(4) -0.0021(4) C26 0.0385(6) 0.0436(6) 0.0295(5) -0.0008(4) 0.0042(4) -0.0024(5) C27 0.0324(6) 0.0357(5) 0.0329(5) -0.0019(4) 0.0023(4) 0.0023(4) C28 0.0315(5) 0.0294(5) 0.0337(5) 0.0001(4) 0.0036(4) 0.0017(4) C29 0.0417(6) 0.0446(6) 0.0337(6) -0.0016(5) 0.0059(5) -0.0032(5) C30 0.0529(7) 0.0454(7) 0.0410(6) 0.0027(5) 0.0158(6) -0.0033(6) C31 0.0440(7) 0.0352(6) 0.0606(8) 0.0023(5) 0.0143(6) -0.0069(5) C32 0.0422(7) 0.0353(6) 0.0575(7) 0.0011(5) -0.0042(6) -0.0077(5) C33 0.0406(6) 0.0328(5) 0.0385(6) 0.0028(4) -0.0022(5) -0.0024(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 N1 C2 1.4014(14) . ? N1 C13 1.4008(14) . ? N1 C14 1.4209(14) . ? C2 C3 1.3959(16) . ? C2 C7 1.4085(16) . ? C3 C4 1.3849(17) . ? C4 C5 1.3944(19) . ? C5 C6 1.3800(19) . ? C6 C7 1.3998(16) . ? C7 C8 1.4422(16) . ? C8 C9 1.3964(16) . ? C8 C13 1.4052(15) . ? C9 C10 1.3757(18) . ? C10 C11 1.3972(17) . ? C11 C12 1.3827(17) . ? C12 C13 1.3925(16) . ? C14 C15 1.3914(16) . ? C14 C19 1.3936(15) . ? C15 C16 1.3846(16) . ? C16 C17 1.3983(15) . ? C17 C18 1.3990(16) . ? C17 C20 1.4709(15) . ? C18 C19 1.3804(16) . ? C20 C21 1.3435(16) . ? C21 C22 1.4951(14) . ? C21 C28 1.4905(15) . ? C22 C23 1.3884(15) . ? C22 C27 1.3914(15) . ? C23 C24 1.3851(16) . ? C24 N25 1.3330(16) . ? N25 C26 1.3391(15) . ? C26 C27 1.3821(16) . ? C28 C29 1.4009(16) . ? C28 C33 1.3933(16) . ? C29 C30 1.3846(17) . ? C30 C31 1.380(2) . ? C31 C32 1.3788(19) . ? C32 C33 1.3862(17) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C14 126.68(9) . . ? C13 N1 C2 107.97(9) . . ? C13 N1 C14 125.23(9) . . ? N1 C2 C7 108.84(9) . . ? C3 C2 N1 129.75(10) . . ? C3 C2 C7 121.38(10) . . ? C4 C3 C2 117.24(11) . . ? C3 C4 C5 122.12(12) . . ? C6 C5 C4 120.60(11) . . ? C5 C6 C7 118.75(12) . . ? C2 C7 C8 107.10(10) . . ? C6 C7 C2 119.90(11) . . ? C6 C7 C8 132.91(11) . . ? C9 C8 C7 133.24(11) . . ? C9 C8 C13 119.74(10) . . ? C13 C8 C7 106.97(10) . . ? C10 C9 C8 118.92(11) . . ? C9 C10 C11 120.75(11) . . ? C12 C11 C10 121.56(11) . . ? C11 C12 C13 117.57(11) . . ? N1 C13 C8 109.10(9) . . ? C12 C13 N1 129.39(10) . . ? C12 C13 C8 121.41(10) . . ? C15 C14 N1 120.85(10) . . ? C15 C14 C19 119.48(10) . . ? C19 C14 N1 119.66(10) . . ? C16 C15 C14 119.76(10) . . ? C15 C16 C17 121.50(10) . . ? C16 C17 C18 117.83(10) . . ? C16 C17 C20 120.52(10) . . ? C18 C17 C20 121.53(10) . . ? C19 C18 C17 121.07(10) . . ? C18 C19 C14 120.33(10) . . ? C21 C20 C17 127.86(10) . . ? C20 C21 C22 122.03(9) . . ? C20 C21 C28 121.06(10) . . ? C28 C21 C22 116.82(9) . . ? C23 C22 C21 122.30(9) . . ? C23 C22 C27 116.67(10) . . ? C27 C22 C21 120.98(9) . . ? C24 C23 C22 119.47(10) . . ? N25 C24 C23 124.30(11) . . ? C24 N25 C26 115.87(10) . . ? N25 C26 C27 124.03(10) . . ? C26 C27 C22 119.65(10) . . ? C29 C28 C21 121.24(10) . . ? C33 C28 C21 121.06(10) . . ? C33 C28 C29 117.70(10) . . ? C30 C29 C28 120.73(11) . . ? C31 C30 C29 120.65(12) . . ? C32 C31 C30 119.32(11) . . ? C31 C32 C33 120.42(12) . . ? C32 C33 C28 121.12(11) . . ? _database_code_depnum_ccdc_archive 'CCDC 928173'