# Electronic Supplementary Material (ESI) for RSC Advances. # This journal is © The Royal Society of Chemistry 2016 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_um08 _database_code_depnum_ccdc_archive 'CCDC 1441546' _audit_update_record ; 2015-12-09 deposited with the CCDC. 2016-07-11 downloaded from the CCDC. ; _audit_creation_date 2013-01-25 _audit_creation_method ; Olex2 1.2-ac2 (compiled 2012.03.27 svn.r2268, GUI svn.r4156) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C37 H33 N3' _chemical_formula_sum 'C37 H33 N3' _chemical_formula_weight 519.66 _chemical_melting_point ? _chemical_oxdiff_formula 'C37 H33 N3' 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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _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 15.0018(6) _cell_length_b 11.1825(4) _cell_length_c 16.9177(7) _cell_angle_alpha 90.00 _cell_angle_beta 110.262(4) _cell_angle_gamma 90.00 _cell_volume 2662.46(17) _cell_formula_units_Z 4 _cell_measurement_reflns_used 2387 _cell_measurement_temperature 173.00(10) _cell_measurement_theta_max 61.7311 _cell_measurement_theta_min 4.8337 _exptl_absorpt_coefficient_mu 0.581 _exptl_absorpt_correction_T_max 0.995 _exptl_absorpt_correction_T_min 0.979 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_crystal_colour 'clear dark red' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier dark _exptl_crystal_colour_primary red _exptl_crystal_density_diffrn 1.296 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 1104 _exptl_crystal_size_max 0.2111 _exptl_crystal_size_mid 0.1581 _exptl_crystal_size_min 0.0368 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0534 _diffrn_reflns_av_unetI/netI 0.0686 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 7256 _diffrn_reflns_theta_full 61.82 _diffrn_reflns_theta_max 61.82 _diffrn_reflns_theta_min 4.84 _diffrn_ambient_temperature 173.00(10) _diffrn_detector_area_resol_mean 10.6144 _diffrn_measured_fraction_theta_full 0.9865 _diffrn_measured_fraction_theta_max 0.9509 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -85.00 -35.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 178.0000 90.0000 50 #__ type_ start__ end____ width___ exp.time_ 2 omega -125.00 -80.00 1.0000 2.4200 omega____ theta____ kappa____ phi______ frames - -43.5000 -94.0000 -120.0000 45 #__ type_ start__ end____ width___ exp.time_ 3 omega 106.00 133.00 1.0000 2.4200 omega____ theta____ kappa____ phi______ frames - 82.4168 125.0000 -150.0000 27 #__ type_ start__ end____ width___ exp.time_ 4 omega 6.00 91.00 1.0000 2.4200 omega____ theta____ kappa____ phi______ frames - 82.4168 -30.0000 120.0000 85 #__ type_ start__ end____ width___ exp.time_ 5 omega 54.00 154.00 1.0000 2.4200 omega____ theta____ kappa____ phi______ frames - 82.4168 61.0000 -90.0000 100 #__ type_ start__ end____ width___ exp.time_ 6 omega 107.00 156.00 1.0000 2.4200 omega____ theta____ kappa____ phi______ frames - 82.4168 125.0000 60.0000 49 #__ type_ start__ end____ width___ exp.time_ 7 omega 59.00 137.00 1.0000 2.4200 omega____ theta____ kappa____ phi______ frames - 82.4168 45.0000 60.0000 78 ; _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.1068692000 _diffrn_orient_matrix_UB_12 -0.0102540000 _diffrn_orient_matrix_UB_13 -0.0511959000 _diffrn_orient_matrix_UB_21 -0.0152008000 _diffrn_orient_matrix_UB_22 -0.0695615000 _diffrn_orient_matrix_UB_23 0.0729623000 _diffrn_orient_matrix_UB_31 -0.0181753000 _diffrn_orient_matrix_UB_32 0.1184284000 _diffrn_orient_matrix_UB_33 0.0383809000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_source 'SuperNova (Cu) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2805 _reflns_number_total 4019 _reflns_odcompleteness_completeness 98.65 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 58.86 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _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 ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.215 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.048 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 367 _refine_ls_number_reflns 4019 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0806 _refine_ls_R_factor_gt 0.0530 _refine_ls_restrained_S_all 1.056 _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^)+(0.0618P)^2^+0.4246P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1277 _refine_ls_wR_factor_ref 0.1517 _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 C1 C 0.71890(17) 0.0646(2) 0.18320(15) 0.0240(6) Uani 1 1 d . . . C2 C 0.63020(17) 0.0451(2) 0.19220(15) 0.0257(6) Uani 1 1 d . . . C3 C 0.62360(19) -0.0356(2) 0.25248(16) 0.0314(6) Uani 1 1 d . . . H3 H 0.5646 -0.0491 0.2575 0.038 Uiso 1 1 calc R . . C4 C 0.70163(19) -0.0962(3) 0.30505(16) 0.0335(7) Uani 1 1 d . . . H4 H 0.6958 -0.1502 0.3448 0.040 Uiso 1 1 calc R . . C5 C 0.78842(18) -0.0745(2) 0.29712(16) 0.0301(6) Uani 1 1 d . . . H5 H 0.8417 -0.1134 0.3333 0.036 Uiso 1 1 calc R . . C6 C 0.79948(17) 0.0035(2) 0.23701(15) 0.0265(6) Uani 1 1 d . . . C7 C 0.89927(17) 0.0218(2) 0.23573(15) 0.0284(6) Uani 1 1 d . . . C8 C 0.89697(17) 0.0918(2) 0.15834(15) 0.0250(6) Uani 1 1 d . . . C9 C 0.97997(18) 0.0967(2) 0.13981(16) 0.0297(6) Uani 1 1 d . . . H9 H 1.0324 0.0535 0.1734 0.036 Uiso 1 1 calc R . . C10 C 0.98831(18) 0.1631(2) 0.07358(15) 0.0285(6) Uani 1 1 d . . . C11 C 0.90913(18) 0.2289(2) 0.02685(16) 0.0304(6) Uani 1 1 d . . . H11 H 0.9134 0.2771 -0.0165 0.036 Uiso 1 1 calc R . . C12 C 0.82424(17) 0.2260(2) 0.04182(15) 0.0264(6) Uani 1 1 d . . . C13 C 0.81585(16) 0.1543(2) 0.10723(15) 0.0241(6) Uani 1 1 d . . . C14 C 0.74455(17) 0.3031(2) -0.01418(15) 0.0267(6) Uani 1 1 d . . . C15 C 0.65228(17) 0.2792(2) 0.00115(15) 0.0254(6) Uani 1 1 d . . . C16 C 0.57129(17) 0.3362(2) -0.05185(15) 0.0271(6) Uani 1 1 d . . . H16 H 0.5774 0.3886 -0.0924 0.033 Uiso 1 1 calc R . . C17 C 0.48195(17) 0.3186(2) -0.04699(15) 0.0270(6) Uani 1 1 d . . . C18 C 0.47622(18) 0.2428(2) 0.01583(16) 0.0276(6) Uani 1 1 d . . . H18 H 0.4171 0.2292 0.0205 0.033 Uiso 1 1 calc R . . C19 C 0.55546(17) 0.1859(2) 0.07246(15) 0.0248(6) Uani 1 1 d . . . C20 C 0.64517(17) 0.2029(2) 0.06504(15) 0.0236(6) Uani 1 1 d . . . C21 C 0.53897(17) 0.1070(2) 0.13916(15) 0.0263(6) Uani 1 1 d . . . C22 C 0.5010(2) 0.1854(3) 0.19542(17) 0.0387(7) Uani 1 1 d . . . H22A H 0.5467 0.2465 0.2217 0.058 Uiso 1 1 calc R . . H22B H 0.4905 0.1367 0.2381 0.058 Uiso 1 1 calc R . . H22C H 0.4423 0.2220 0.1616 0.058 Uiso 1 1 calc R . . C23 C 0.46475(19) 0.0103(3) 0.09670(18) 0.0382(7) Uani 1 1 d . . . H23A H 0.4101 0.0470 0.0562 0.057 Uiso 1 1 calc R . . H23B H 0.4462 -0.0301 0.1386 0.057 Uiso 1 1 calc R . . H23C H 0.4918 -0.0464 0.0688 0.057 Uiso 1 1 calc R . . C24 C 0.9565(2) 0.0928(3) 0.31426(17) 0.0522(9) Uani 1 1 d . . . H24A H 0.9287 0.1707 0.3122 0.078 Uiso 1 1 calc R . . H24B H 1.0209 0.1011 0.3161 0.078 Uiso 1 1 calc R . . H24C H 0.9557 0.0514 0.3637 0.078 Uiso 1 1 calc R . . C25 C 0.9477(2) -0.1010(3) 0.2361(2) 0.0538(9) Uani 1 1 d . . . H25A H 0.9466 -0.1470 0.2837 0.081 Uiso 1 1 calc R . . H25B H 1.0124 -0.0886 0.2398 0.081 Uiso 1 1 calc R . . H25C H 0.9142 -0.1434 0.1851 0.081 Uiso 1 1 calc R . . C26 C 0.7724(2) 0.4358(2) 0.00661(19) 0.0373(7) Uani 1 1 d . . . H26A H 0.7224 0.4863 -0.0281 0.056 Uiso 1 1 calc R . . H26B H 0.8300 0.4525 -0.0041 0.056 Uiso 1 1 calc R . . H26C H 0.7820 0.4507 0.0649 0.056 Uiso 1 1 calc R . . C27 C 0.72958(19) 0.2781(3) -0.10802(16) 0.0359(7) Uani 1 1 d . . . H27A H 0.7114 0.1961 -0.1209 0.054 Uiso 1 1 calc R . . H27B H 0.7876 0.2934 -0.1182 0.054 Uiso 1 1 calc R . . H27C H 0.6804 0.3294 -0.1431 0.054 Uiso 1 1 calc R . . C31 C 0.39638(18) 0.3754(2) -0.10817(16) 0.0279(6) Uani 1 1 d . . . C32 C 0.39717(19) 0.4927(2) -0.13586(16) 0.0330(7) Uani 1 1 d . . . H32 H 0.4522 0.5386 -0.1157 0.040 Uiso 1 1 calc R . . C33 C 0.3152(2) 0.5403(3) -0.19369(17) 0.0398(7) Uani 1 1 d . . . H33 H 0.3175 0.6189 -0.2110 0.048 Uiso 1 1 calc R . . C35 C 0.2342(2) 0.3688(3) -0.20054(18) 0.0392(7) Uani 1 1 d . . . H35 H 0.1786 0.3246 -0.2228 0.047 Uiso 1 1 calc R . . C36 C 0.31192(18) 0.3129(3) -0.14307(16) 0.0328(7) Uani 1 1 d . . . H36 H 0.3076 0.2337 -0.1279 0.039 Uiso 1 1 calc R . . C41 C 1.07485(18) 0.1622(2) 0.05122(15) 0.0290(6) Uani 1 1 d . . . C42 C 1.10005(19) 0.2569(3) 0.01005(17) 0.0342(7) Uani 1 1 d . . . H42 H 1.0623 0.3251 -0.0034 0.041 Uiso 1 1 calc R . . C43 C 1.18087(19) 0.2501(3) -0.01089(17) 0.0353(7) Uani 1 1 d . . . H43 H 1.1950 0.3149 -0.0389 0.042 Uiso 1 1 calc R . . C45 C 1.2161(2) 0.0672(3) 0.04532(19) 0.0402(7) Uani 1 1 d . . . H45 H 1.2558 0.0007 0.0581 0.048 Uiso 1 1 calc R . . C46 C 1.13626(18) 0.0651(3) 0.06861(17) 0.0349(7) Uani 1 1 d . . . H46 H 1.1237 -0.0016 0.0960 0.042 Uiso 1 1 calc R . . N1 N 0.72760(13) 0.14474(19) 0.12087(12) 0.0246(5) Uani 1 1 d . . . N34 N 0.23306(16) 0.4815(2) -0.22636(14) 0.0409(6) Uani 1 1 d . . . N44 N 1.23983(16) 0.1578(2) 0.00610(15) 0.0390(6) 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 0.0251(14) 0.0289(14) 0.0178(13) -0.0018(11) 0.0071(11) -0.0008(11) C2 0.0255(14) 0.0302(15) 0.0214(13) -0.0013(12) 0.0080(11) -0.0033(12) C3 0.0287(15) 0.0372(16) 0.0282(15) 0.0041(13) 0.0099(12) -0.0051(13) C4 0.0361(16) 0.0392(16) 0.0252(14) 0.0079(13) 0.0108(13) -0.0036(13) C5 0.0298(15) 0.0336(15) 0.0245(14) 0.0046(12) 0.0063(12) -0.0013(12) C6 0.0282(14) 0.0307(15) 0.0197(13) -0.0001(12) 0.0072(11) -0.0020(12) C7 0.0215(13) 0.0372(15) 0.0231(13) 0.0050(12) 0.0037(11) -0.0023(12) C8 0.0257(14) 0.0286(14) 0.0184(13) 0.0010(11) 0.0048(11) 0.0003(12) C9 0.0246(14) 0.0347(15) 0.0266(14) 0.0005(13) 0.0046(11) 0.0008(12) C10 0.0276(14) 0.0369(16) 0.0216(13) -0.0011(12) 0.0093(11) -0.0022(12) C11 0.0289(15) 0.0388(16) 0.0232(14) 0.0055(13) 0.0086(12) -0.0007(13) C12 0.0229(13) 0.0325(15) 0.0220(13) 0.0035(12) 0.0055(11) 0.0004(12) C13 0.0212(13) 0.0293(14) 0.0211(13) -0.0015(12) 0.0065(11) -0.0033(11) C14 0.0256(14) 0.0324(15) 0.0218(13) 0.0036(12) 0.0079(11) 0.0000(12) C15 0.0243(14) 0.0299(14) 0.0207(13) 0.0004(12) 0.0063(11) 0.0007(12) C16 0.0283(14) 0.0319(14) 0.0200(13) 0.0047(12) 0.0068(11) 0.0015(12) C17 0.0265(14) 0.0319(15) 0.0208(13) 0.0004(12) 0.0058(11) 0.0008(12) C18 0.0249(14) 0.0325(15) 0.0252(14) -0.0011(12) 0.0084(11) -0.0023(12) C19 0.0251(14) 0.0301(14) 0.0199(13) -0.0001(11) 0.0089(11) -0.0023(12) C20 0.0243(14) 0.0258(14) 0.0190(13) -0.0007(11) 0.0051(11) -0.0010(11) C21 0.0241(14) 0.0328(15) 0.0231(13) 0.0016(12) 0.0094(11) -0.0007(12) C22 0.0396(17) 0.0447(18) 0.0350(16) 0.0070(14) 0.0169(14) 0.0117(14) C23 0.0273(15) 0.0473(18) 0.0343(16) 0.0058(15) 0.0035(12) -0.0073(14) C24 0.0438(18) 0.085(3) 0.0237(15) -0.0014(17) 0.0065(14) -0.0268(18) C25 0.051(2) 0.049(2) 0.070(2) 0.0255(18) 0.0318(19) 0.0174(17) C26 0.0336(16) 0.0352(16) 0.0429(17) 0.0067(14) 0.0132(14) -0.0012(13) C27 0.0333(15) 0.0490(18) 0.0261(15) 0.0077(14) 0.0113(12) 0.0050(14) C31 0.0244(14) 0.0364(16) 0.0220(13) -0.0004(12) 0.0067(11) 0.0024(12) C32 0.0343(16) 0.0340(16) 0.0271(15) 0.0003(13) 0.0059(12) -0.0012(13) C33 0.0468(19) 0.0384(17) 0.0291(15) 0.0064(14) 0.0068(14) 0.0075(15) C35 0.0287(15) 0.0472(19) 0.0356(17) 0.0001(15) 0.0034(13) -0.0019(14) C36 0.0275(15) 0.0375(16) 0.0289(15) 0.0022(13) 0.0042(12) 0.0029(13) C41 0.0237(14) 0.0384(16) 0.0220(13) -0.0023(12) 0.0041(11) -0.0043(12) C42 0.0302(15) 0.0373(16) 0.0357(16) 0.0022(13) 0.0123(13) 0.0005(13) C43 0.0332(16) 0.0399(17) 0.0355(16) 0.0007(14) 0.0154(13) -0.0035(14) C45 0.0333(16) 0.0427(18) 0.0484(18) 0.0052(15) 0.0191(15) 0.0038(14) C46 0.0289(15) 0.0408(17) 0.0356(16) 0.0027(14) 0.0118(13) -0.0026(13) N1 0.0221(11) 0.0314(12) 0.0199(11) 0.0052(10) 0.0070(9) -0.0002(9) N34 0.0368(14) 0.0466(16) 0.0293(13) 0.0010(12) -0.0014(11) 0.0053(12) N44 0.0333(13) 0.0440(15) 0.0438(15) -0.0009(12) 0.0184(12) -0.0019(12) _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 C2 1.408(3) . ? C1 C6 1.412(3) . ? C1 N1 1.424(3) . ? C2 C3 1.391(3) . ? C2 C21 1.519(4) . ? C3 C4 1.378(4) . ? C4 C5 1.376(4) . ? C5 C6 1.393(3) . ? C6 C7 1.518(3) . ? C7 C8 1.515(3) . ? C7 C24 1.531(4) . ? C7 C25 1.553(4) . ? C8 C9 1.386(3) . ? C8 C13 1.410(3) . ? C9 C10 1.385(4) . ? C10 C11 1.388(4) . ? C10 C41 1.473(3) . ? C11 C12 1.382(3) . ? C12 C13 1.407(3) . ? C12 C14 1.512(3) . ? C13 N1 1.424(3) . ? C14 C15 1.518(3) . ? C14 C26 1.548(4) . ? C14 C27 1.550(3) . ? C15 C16 1.390(3) . ? C15 C20 1.410(3) . ? C16 C17 1.385(3) . ? C17 C18 1.385(3) . ? C17 C31 1.484(3) . ? C18 C19 1.395(3) . ? C19 C20 1.407(3) . ? C19 C21 1.519(3) . ? C20 N1 1.427(3) . ? C21 C22 1.540(4) . ? C21 C23 1.540(4) . ? C31 C32 1.395(4) . ? C31 C36 1.387(4) . ? C32 C33 1.386(4) . ? C33 N34 1.335(4) . ? C35 C36 1.383(4) . ? C35 N34 1.332(4) . ? C41 C42 1.390(4) . ? C41 C46 1.388(4) . ? C42 C43 1.378(4) . ? C43 N44 1.324(4) . ? C45 C46 1.385(4) . ? C45 N44 1.325(3) . ? 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 C1 C6 119.1(2) . . ? C2 C1 N1 120.7(2) . . ? C6 C1 N1 120.3(2) . . ? C1 C2 C21 123.9(2) . . ? C3 C2 C1 119.3(2) . . ? C3 C2 C21 116.8(2) . . ? C4 C3 C2 122.1(2) . . ? C5 C4 C3 118.1(2) . . ? C4 C5 C6 122.5(2) . . ? C1 C6 C7 123.6(2) . . ? C5 C6 C1 118.8(2) . . ? C5 C6 C7 117.5(2) . . ? C6 C7 C24 108.5(2) . . ? C6 C7 C25 110.1(2) . . ? C8 C7 C6 110.8(2) . . ? C8 C7 C24 108.7(2) . . ? C8 C7 C25 109.3(2) . . ? C24 C7 C25 109.5(2) . . ? C9 C8 C7 117.5(2) . . ? C9 C8 C13 119.6(2) . . ? C13 C8 C7 122.8(2) . . ? C10 C9 C8 122.9(2) . . ? C9 C10 C11 116.5(2) . . ? C9 C10 C41 122.6(2) . . ? C11 C10 C41 120.9(2) . . ? C12 C11 C10 123.0(2) . . ? C11 C12 C13 119.8(2) . . ? C11 C12 C14 116.8(2) . . ? C13 C12 C14 123.5(2) . . ? C8 C13 N1 121.1(2) . . ? C12 C13 C8 118.1(2) . . ? C12 C13 N1 120.7(2) . . ? C12 C14 C15 111.3(2) . . ? C12 C14 C26 108.1(2) . . ? C12 C14 C27 110.0(2) . . ? C15 C14 C26 108.7(2) . . ? C15 C14 C27 109.0(2) . . ? C26 C14 C27 109.7(2) . . ? C16 C15 C14 117.0(2) . . ? C16 C15 C20 119.4(2) . . ? C20 C15 C14 123.6(2) . . ? C17 C16 C15 122.9(2) . . ? C16 C17 C18 116.8(2) . . ? C16 C17 C31 121.2(2) . . ? C18 C17 C31 121.9(2) . . ? C17 C18 C19 122.8(2) . . ? C18 C19 C20 119.4(2) . . ? C18 C19 C21 117.1(2) . . ? C20 C19 C21 123.5(2) . . ? C15 C20 N1 120.3(2) . . ? C19 C20 C15 118.6(2) . . ? C19 C20 N1 121.1(2) . . ? C2 C21 C22 110.1(2) . . ? C2 C21 C23 108.3(2) . . ? C19 C21 C2 111.0(2) . . ? C19 C21 C22 108.6(2) . . ? C19 C21 C23 109.8(2) . . ? C23 C21 C22 109.0(2) . . ? C32 C31 C17 122.1(2) . . ? C36 C31 C17 121.5(2) . . ? C36 C31 C32 116.3(2) . . ? C33 C32 C31 119.3(3) . . ? N34 C33 C32 124.7(3) . . ? N34 C35 C36 124.8(3) . . ? C35 C36 C31 119.7(3) . . ? C42 C41 C10 122.7(2) . . ? C46 C41 C10 122.0(2) . . ? C46 C41 C42 115.3(2) . . ? C43 C42 C41 120.2(3) . . ? N44 C43 C42 124.6(3) . . ? N44 C45 C46 124.4(3) . . ? C45 C46 C41 120.1(3) . . ? C1 N1 C13 119.7(2) . . ? C1 N1 C20 119.77(19) . . ? C13 N1 C20 119.98(19) . . ? C35 N34 C33 115.1(2) . . ? C43 N44 C45 115.4(2) . . ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 1 6 -6 0.0938 0.8220 5.9946 -6.0649 0.1612 -0.8720 0.4622 -4 5 7 0.0601 -3.5664 5.4216 7.1119 -0.0386 0.1960 0.9798 -3 -2 10 0.0948 -3.0297 -2.4325 10.3413 -0.1807 0.9698 0.1639 4 0 -11 0.0894 3.6495 0.4632 -10.9499 0.1658 -0.8866 -0.4317 9 -1 1 0.0290 8.6875 -1.3925 0.8241 -0.9563 0.0249 -0.2912 -9 2 -1 0.0052 -8.7044 1.6097 -0.6175 0.9453 -0.0247 0.3251 9 1 0 0.0413 9.1458 0.5037 -0.1076 -0.9771 -0.1819 -0.1107 3 6 -5 0.0990 3.0661 6.2130 -5.4187 -0.1140 -0.8742 0.4721 6 0 -10 0.0858 6.0421 0.2068 -10.4241 -0.1142 -0.8668 -0.4854 3 -6 -6 0.0755 3.3232 -6.1134 -5.6019 -0.0057 -0.0340 -0.9994 -2 -7 4 0.0988 -1.9549 -6.8417 3.5156 0.0991 0.7621 -0.6398 -6 -2 10 0.0871 -5.8556 -1.7277 10.1346 0.1246 0.9486 0.2908