# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_publication_text _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 #TrackingRef '1.cif' _publ_contact_author_name 'Bedford, Robin B' _publ_contact_author_address ;School of Chemistry University of Bristol Cantock's Close Bristol BS8 1TS ; _publ_contact_author_email r.bedford@bris.ac.uk _publ_contact_author_phone 01173318298 loop_ _publ_author_name _publ_author_address M.Haddow ;School of Chemistry University of Bristol Cantock's Close Bristol BS8 1TS ; R.Bedford ;School of Chemistry University of Bristol Cantock's Close Bristol BS8 1TS ; R.Sankey ;School of Chemistry University of Bristol Cantock's Close Bristol BS8 1TS ; N.Fey ;School of Chemistry University of Bristol Cantock's Close Bristol BS8 1TS ; data_rs3_27_2_0m _database_code_depnum_ccdc_archive 'CCDC 789828' #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H18 N2' _chemical_formula_sum 'C17 H18 N2' _chemical_formula_weight 250.33 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 -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.2164(4) _cell_length_b 13.3376(5) _cell_length_c 18.9472(7) _cell_angle_alpha 83.895(1) _cell_angle_beta 89.499(1) _cell_angle_gamma 76.898(1) _cell_volume 2744.71(17) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9916 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 27.51 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.212 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6879 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details 'SADABS V2008/1' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 ? _diffrn_reflns_number 98242 _diffrn_reflns_av_R_equivalents 0.0380 _diffrn_reflns_av_sigmaI/netI 0.0222 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 27.58 _reflns_number_total 12662 _reflns_number_gt 10755 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex II' _computing_cell_refinement 'Bruker Apex II' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0609P)^2^+0.8789P] 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 12662 _refine_ls_number_parameters 709 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0507 _refine_ls_R_factor_gt 0.0419 _refine_ls_wR_factor_ref 0.1150 _refine_ls_wR_factor_gt 0.1081 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 0.30168(8) 0.82617(7) 0.08463(5) 0.01657(18) Uani 1 1 d . . . N2 N 0.13730(8) 0.77310(7) 0.15447(5) 0.01528(18) Uani 1 1 d . . . H1N H 0.0971(12) 0.8212(11) 0.1808(7) 0.018 Uiso 1 1 d . . . C1 C 0.27167(9) 0.76858(8) 0.15000(5) 0.0148(2) Uani 1 1 d . . . C2 C 0.31431(9) 0.76165(8) 0.03056(6) 0.0157(2) Uani 1 1 d . . . C3 C 0.31166(10) 0.78842(9) -0.04240(6) 0.0197(2) Uani 1 1 d . . . H3 H 0.2980 0.8588 -0.0618 0.024 Uiso 1 1 calc R . . C4 C 0.32971(10) 0.70871(9) -0.08632(6) 0.0215(2) Uani 1 1 d . . . H4 H 0.3273 0.7255 -0.1364 0.026 Uiso 1 1 calc R . . C5 C 0.35112(10) 0.60556(9) -0.05846(6) 0.0209(2) Uani 1 1 d . . . H5 H 0.3639 0.5526 -0.0894 0.025 Uiso 1 1 calc R . . C6 C 0.35395(10) 0.57958(8) 0.01508(6) 0.0179(2) Uani 1 1 d . . . H6 H 0.3692 0.5092 0.0346 0.021 Uiso 1 1 calc R . . C7 C 0.33419(9) 0.65792(8) 0.05867(5) 0.0152(2) Uani 1 1 d . . . C8 C 0.32755(10) 0.65177(8) 0.13908(5) 0.0157(2) Uani 1 1 d . . . C9 C 0.22816(10) 0.59845(8) 0.16585(5) 0.0172(2) Uani 1 1 d . . . C10 C 0.22894(12) 0.49390(9) 0.17765(6) 0.0244(2) Uani 1 1 d . . . H10 H 0.3020 0.4431 0.1723 0.029 Uiso 1 1 calc R . . C11 C 0.12065(14) 0.46461(10) 0.19744(7) 0.0306(3) Uani 1 1 d . . . H11 H 0.1199 0.3933 0.2058 0.037 Uiso 1 1 calc R . . C12 C 0.01387(13) 0.53923(10) 0.20494(7) 0.0292(3) Uani 1 1 d . . . H12 H -0.0591 0.5181 0.2186 0.035 Uiso 1 1 calc R . . C13 C 0.01199(11) 0.64437(9) 0.19283(6) 0.0224(2) Uani 1 1 d . . . H13 H -0.0612 0.6952 0.1977 0.027 Uiso 1 1 calc R . . C14 C 0.12059(10) 0.67255(8) 0.17347(5) 0.0166(2) Uani 1 1 d . . . C15 C 0.24247(11) 0.93481(8) 0.06887(6) 0.0229(2) Uani 1 1 d . . . H15A H 0.2855 0.9660 0.0303 0.034 Uiso 1 1 calc R . . H15B H 0.2448 0.9705 0.1113 0.034 Uiso 1 1 calc R . . H15C H 0.1572 0.9413 0.0544 0.034 Uiso 1 1 calc R . . C16 C 0.31699(10) 0.80665(9) 0.21531(6) 0.0210(2) Uani 1 1 d . . . H16A H 0.4046 0.8047 0.2109 0.031 Uiso 1 1 calc R . . H16B H 0.3036 0.7620 0.2577 0.031 Uiso 1 1 calc R . . H16C H 0.2720 0.8779 0.2194 0.031 Uiso 1 1 calc R . . C17 C 0.45344(10) 0.60518(9) 0.17360(6) 0.0228(2) Uani 1 1 d . . . H17A H 0.4476 0.6064 0.2252 0.034 Uiso 1 1 calc R . . H17B H 0.5118 0.6458 0.1551 0.034 Uiso 1 1 calc R . . H17C H 0.4816 0.5335 0.1626 0.034 Uiso 1 1 calc R . . N3 N 0.95647(9) 0.25481(7) 0.38598(5) 0.0201(2) Uani 1 1 d . . . N4 N 0.95944(9) 0.32594(8) 0.50005(6) 0.0241(2) Uani 1 1 d . . . H2N H 1.0350(14) 0.3167(11) 0.5184(8) 0.029 Uiso 1 1 d . . . C18 C 0.94038(10) 0.23766(8) 0.46320(6) 0.0181(2) Uani 1 1 d . . . C19 C 0.84484(10) 0.30146(8) 0.35353(6) 0.0170(2) Uani 1 1 d . . . C20 C 0.82213(11) 0.34723(9) 0.28371(6) 0.0226(2) Uani 1 1 d . . . H20 H 0.8875 0.3520 0.2523 0.027 Uiso 1 1 calc R . . C21 C 0.70096(12) 0.38557(9) 0.26152(6) 0.0274(3) Uani 1 1 d . . . H21 H 0.6839 0.4170 0.2142 0.033 Uiso 1 1 calc R . . C22 C 0.60469(12) 0.37901(10) 0.30662(7) 0.0289(3) Uani 1 1 d . . . H22 H 0.5227 0.4055 0.2902 0.035 Uiso 1 1 calc R . . C23 C 0.62861(11) 0.33328(9) 0.37650(6) 0.0234(2) Uani 1 1 d . . . H23 H 0.5631 0.3284 0.4078 0.028 Uiso 1 1 calc R . . C24 C 0.74823(10) 0.29533(8) 0.39947(5) 0.0165(2) Uani 1 1 d . . . C25 C 0.79867(10) 0.24273(8) 0.47168(5) 0.0166(2) Uani 1 1 d . . . C26 C 0.76334(11) 0.31239(8) 0.53009(5) 0.0195(2) Uani 1 1 d . . . C27 C 0.65463(12) 0.33597(10) 0.56633(6) 0.0270(3) Uani 1 1 d . . . H27 H 0.5883 0.3062 0.5561 0.032 Uiso 1 1 calc R . . C28 C 0.64413(14) 0.40426(10) 0.61822(7) 0.0344(3) Uani 1 1 d . . . H28 H 0.5700 0.4214 0.6434 0.041 Uiso 1 1 calc R . . C29 C 0.74136(15) 0.44699(10) 0.63308(6) 0.0350(3) Uani 1 1 d . . . H29 H 0.7335 0.4922 0.6692 0.042 Uiso 1 1 calc R . . C30 C 0.85058(13) 0.42492(9) 0.59611(7) 0.0300(3) Uani 1 1 d . . . H30 H 0.9164 0.4556 0.6059 0.036 Uiso 1 1 calc R . . C31 C 0.86080(11) 0.35667(8) 0.54437(6) 0.0220(2) Uani 1 1 d . . . C32 C 1.06698(12) 0.28282(12) 0.35932(8) 0.0355(3) Uani 1 1 d . . . H32A H 1.0765 0.2704 0.3093 0.053 Uiso 1 1 calc R . . H32B H 1.1377 0.2408 0.3869 0.053 Uiso 1 1 calc R . . H32C H 1.0617 0.3563 0.3637 0.053 Uiso 1 1 calc R . . C33 C 1.02665(11) 0.13752(9) 0.49284(6) 0.0243(2) Uani 1 1 d . . . H33A H 1.0155 0.0811 0.4662 0.036 Uiso 1 1 calc R . . H33B H 1.0088 0.1217 0.5430 0.036 Uiso 1 1 calc R . . H33C H 1.1114 0.1450 0.4885 0.036 Uiso 1 1 calc R . . C34 C 0.76379(12) 0.13833(9) 0.48779(6) 0.0242(2) Uani 1 1 d . . . H34A H 0.7990 0.1050 0.5339 0.036 Uiso 1 1 calc R . . H34B H 0.7956 0.0939 0.4507 0.036 Uiso 1 1 calc R . . H34C H 0.6744 0.1492 0.4891 0.036 Uiso 1 1 calc R . . N5 N 0.68112(8) 0.67087(7) 0.40088(5) 0.01774(19) Uani 1 1 d . . . N6 N 0.86226(8) 0.71926(7) 0.34791(5) 0.01642(18) Uani 1 1 d . . . H3N H 0.9099(13) 0.6680(11) 0.3265(7) 0.020 Uiso 1 1 d . . . C35 C 0.72737(9) 0.72989(8) 0.34135(5) 0.0159(2) Uani 1 1 d . . . C36 C 0.66545(9) 0.73052(8) 0.45781(6) 0.0168(2) Uani 1 1 d . . . C37 C 0.65314(10) 0.69862(9) 0.52926(6) 0.0209(2) Uani 1 1 d . . . H37 H 0.6603 0.6276 0.5455 0.025 Uiso 1 1 calc R . . C38 C 0.62993(10) 0.77442(10) 0.57635(6) 0.0229(2) Uani 1 1 d . . . H38 H 0.6202 0.7544 0.6253 0.027 Uiso 1 1 calc R . . C39 C 0.62078(10) 0.87806(9) 0.55331(6) 0.0219(2) Uani 1 1 d . . . H39 H 0.6047 0.9282 0.5863 0.026 Uiso 1 1 calc R . . C40 C 0.63533(10) 0.90886(9) 0.48132(6) 0.0184(2) Uani 1 1 d . . . H40 H 0.6294 0.9797 0.4651 0.022 Uiso 1 1 calc R . . C41 C 0.65842(9) 0.83474(8) 0.43441(5) 0.0157(2) Uani 1 1 d . . . C42 C 0.67565(10) 0.84633(8) 0.35443(5) 0.0155(2) Uani 1 1 d . . . C43 C 0.78189(10) 0.89518(8) 0.33338(5) 0.0169(2) Uani 1 1 d . . . C44 C 0.78779(11) 0.99797(9) 0.32082(6) 0.0215(2) Uani 1 1 d . . . H44 H 0.7160 1.0514 0.3227 0.026 Uiso 1 1 calc R . . C45 C 0.90076(12) 1.02232(9) 0.30533(6) 0.0262(3) Uani 1 1 d . . . H45 H 0.9060 1.0926 0.2966 0.031 Uiso 1 1 calc R . . C46 C 1.00535(11) 0.94352(10) 0.30272(6) 0.0249(2) Uani 1 1 d . . . H46 H 1.0816 0.9610 0.2924 0.030 Uiso 1 1 calc R . . C47 C 1.00096(10) 0.83940(9) 0.31494(6) 0.0206(2) Uani 1 1 d . . . H47 H 1.0726 0.7859 0.3128 0.025 Uiso 1 1 calc R . . C48 C 0.88773(10) 0.81675(8) 0.33040(5) 0.0168(2) Uani 1 1 d . . . C49 C 0.73238(12) 0.55994(9) 0.41411(7) 0.0257(2) Uani 1 1 d . . . H49A H 0.8172 0.5478 0.4313 0.039 Uiso 1 1 calc R . . H49B H 0.7306 0.5280 0.3700 0.039 Uiso 1 1 calc R . . H49C H 0.6839 0.5293 0.4500 0.039 Uiso 1 1 calc R . . C50 C 0.69284(11) 0.70030(9) 0.27021(6) 0.0212(2) Uani 1 1 d . . . H50A H 0.7363 0.6290 0.2649 0.032 Uiso 1 1 calc R . . H50B H 0.7157 0.7473 0.2318 0.032 Uiso 1 1 calc R . . H50C H 0.6043 0.7055 0.2681 0.032 Uiso 1 1 calc R . . C51 C 0.55412(10) 0.89877(9) 0.31656(6) 0.0213(2) Uani 1 1 d . . . H51A H 0.5283 0.9701 0.3286 0.032 Uiso 1 1 calc R . . H51B H 0.4917 0.8605 0.3317 0.032 Uiso 1 1 calc R . . H51C H 0.5645 0.8993 0.2651 0.032 Uiso 1 1 calc R . . N7 N 0.90532(9) 0.82633(7) 0.91219(5) 0.0209(2) Uani 1 1 d . . . N8 N 0.93365(9) 0.81535(8) 1.03860(5) 0.0240(2) Uani 1 1 d . . . H4N H 1.0003(14) 0.8026(11) 1.0626(8) 0.029 Uiso 1 1 d . . . C52 C 0.91373(10) 0.75841(8) 0.98023(6) 0.0194(2) Uani 1 1 d . . . C53 C 0.80741(10) 0.81861(8) 0.87176(6) 0.0200(2) Uani 1 1 d . . . C54 C 0.78148(12) 0.85292(9) 0.80032(6) 0.0259(3) Uani 1 1 d . . . H54 H 0.8362 0.8841 0.7719 0.031 Uiso 1 1 calc R . . C55 C 0.67186(13) 0.83985(10) 0.77187(7) 0.0325(3) Uani 1 1 d . . . H55 H 0.6519 0.8633 0.7234 0.039 Uiso 1 1 calc R . . C56 C 0.59205(12) 0.79377(11) 0.81240(7) 0.0324(3) Uani 1 1 d . . . H56 H 0.5184 0.7856 0.7917 0.039 Uiso 1 1 calc R . . C57 C 0.61982(11) 0.75888(10) 0.88427(7) 0.0266(3) Uani 1 1 d . . . H57 H 0.5656 0.7268 0.9125 0.032 Uiso 1 1 calc R . . C58 C 0.72674(10) 0.77186(8) 0.91320(6) 0.0195(2) Uani 1 1 d . . . C59 C 0.77761(10) 0.74515(8) 0.98817(6) 0.0187(2) Uani 1 1 d . . . C60 C 0.72633(10) 0.82711(8) 1.03770(6) 0.0183(2) Uani 1 1 d . . . C61 C 0.60680(11) 0.86606(9) 1.05629(6) 0.0230(2) Uani 1 1 d . . . H61 H 0.5414 0.8453 1.0348 0.028 Uiso 1 1 calc R . . C62 C 0.58327(12) 0.93641(10) 1.10717(6) 0.0261(3) Uani 1 1 d . . . H62 H 0.5014 0.9653 1.1195 0.031 Uiso 1 1 calc R . . C63 C 0.68018(12) 0.96389(9) 1.13966(6) 0.0242(2) Uani 1 1 d . . . H63 H 0.6635 1.0100 1.1753 0.029 Uiso 1 1 calc R . . C64 C 0.80098(11) 0.92539(9) 1.12117(6) 0.0223(2) Uani 1 1 d . . . H64 H 0.8665 0.9444 1.1438 0.027 Uiso 1 1 calc R . . C65 C 0.82327(10) 0.85822(8) 1.06860(6) 0.0191(2) Uani 1 1 d . . . C66 C 1.01084(11) 0.85768(10) 0.88151(7) 0.0291(3) Uani 1 1 d . . . H66A H 1.0562 0.8035 0.8540 0.044 Uiso 1 1 calc R . . H66B H 1.0639 0.8686 0.9194 0.044 Uiso 1 1 calc R . . H66C H 0.9842 0.9222 0.8502 0.044 Uiso 1 1 calc R . . C67 C 1.01310(11) 0.66015(9) 0.97811(7) 0.0265(3) Uani 1 1 d . . . H67A H 1.0930 0.6780 0.9726 0.040 Uiso 1 1 calc R . . H67B H 0.9974 0.6241 0.9379 0.040 Uiso 1 1 calc R . . H67C H 1.0130 0.6150 1.0224 0.040 Uiso 1 1 calc R . . C68 C 0.76545(12) 0.63884(9) 1.02244(7) 0.0281(3) Uani 1 1 d . . . H68A H 0.6786 0.6389 1.0289 0.042 Uiso 1 1 calc R . . H68B H 0.8078 0.6237 1.0687 0.042 Uiso 1 1 calc R . . H68C H 0.8021 0.5858 0.9917 0.042 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 0.0176(4) 0.0144(4) 0.0180(4) -0.0019(3) 0.0016(3) -0.0042(3) N2 0.0147(4) 0.0146(4) 0.0165(4) -0.0032(3) 0.0016(3) -0.0026(3) C1 0.0141(5) 0.0141(5) 0.0158(5) -0.0019(4) -0.0009(4) -0.0018(4) C2 0.0111(4) 0.0184(5) 0.0179(5) -0.0026(4) 0.0012(4) -0.0038(4) C3 0.0179(5) 0.0214(5) 0.0192(5) 0.0022(4) 0.0017(4) -0.0057(4) C4 0.0190(5) 0.0307(6) 0.0146(5) -0.0014(4) 0.0027(4) -0.0057(4) C5 0.0180(5) 0.0273(6) 0.0177(5) -0.0083(4) 0.0021(4) -0.0033(4) C6 0.0154(5) 0.0181(5) 0.0191(5) -0.0030(4) -0.0001(4) -0.0009(4) C7 0.0117(4) 0.0184(5) 0.0150(5) -0.0018(4) -0.0004(4) -0.0021(4) C8 0.0179(5) 0.0139(5) 0.0140(5) -0.0028(4) -0.0013(4) -0.0005(4) C9 0.0235(5) 0.0164(5) 0.0115(5) -0.0015(4) 0.0004(4) -0.0045(4) C10 0.0377(7) 0.0166(5) 0.0174(5) -0.0011(4) 0.0029(5) -0.0035(5) C11 0.0522(8) 0.0197(6) 0.0239(6) -0.0020(5) 0.0083(5) -0.0169(6) C12 0.0387(7) 0.0309(7) 0.0239(6) -0.0043(5) 0.0097(5) -0.0201(6) C13 0.0254(6) 0.0256(6) 0.0182(5) -0.0040(4) 0.0048(4) -0.0092(5) C14 0.0221(5) 0.0173(5) 0.0109(4) -0.0019(4) 0.0001(4) -0.0055(4) C15 0.0273(6) 0.0146(5) 0.0259(6) -0.0010(4) 0.0005(5) -0.0038(4) C16 0.0214(5) 0.0208(5) 0.0210(5) -0.0071(4) -0.0035(4) -0.0032(4) C17 0.0206(5) 0.0246(6) 0.0192(5) -0.0042(4) -0.0048(4) 0.0043(4) N3 0.0179(5) 0.0220(5) 0.0195(5) -0.0004(4) 0.0020(4) -0.0034(4) N4 0.0211(5) 0.0202(5) 0.0319(5) -0.0095(4) -0.0059(4) -0.0033(4) C18 0.0195(5) 0.0158(5) 0.0189(5) -0.0028(4) -0.0022(4) -0.0031(4) C19 0.0210(5) 0.0126(5) 0.0177(5) -0.0031(4) -0.0001(4) -0.0039(4) C20 0.0323(6) 0.0173(5) 0.0175(5) -0.0023(4) 0.0036(4) -0.0040(5) C21 0.0408(7) 0.0224(6) 0.0161(5) -0.0022(4) -0.0076(5) -0.0010(5) C22 0.0263(6) 0.0298(6) 0.0281(6) -0.0058(5) -0.0115(5) 0.0001(5) C23 0.0200(5) 0.0268(6) 0.0241(6) -0.0049(5) -0.0012(4) -0.0056(5) C24 0.0206(5) 0.0142(5) 0.0153(5) -0.0034(4) -0.0012(4) -0.0046(4) C25 0.0192(5) 0.0152(5) 0.0155(5) -0.0014(4) -0.0003(4) -0.0040(4) C26 0.0283(6) 0.0154(5) 0.0126(5) 0.0004(4) -0.0014(4) -0.0009(4) C27 0.0355(7) 0.0245(6) 0.0187(5) 0.0006(4) 0.0058(5) -0.0033(5) C28 0.0500(8) 0.0286(7) 0.0182(6) -0.0014(5) 0.0104(5) 0.0033(6) C29 0.0621(9) 0.0207(6) 0.0145(5) -0.0040(4) -0.0060(6) 0.0078(6) C30 0.0428(7) 0.0186(6) 0.0250(6) -0.0054(5) -0.0152(5) 0.0028(5) C31 0.0292(6) 0.0149(5) 0.0190(5) -0.0010(4) -0.0079(4) 0.0011(4) C32 0.0216(6) 0.0456(8) 0.0382(7) 0.0014(6) 0.0067(5) -0.0085(6) C33 0.0260(6) 0.0199(6) 0.0239(6) -0.0033(4) -0.0064(5) 0.0015(5) C34 0.0310(6) 0.0179(5) 0.0253(6) -0.0016(4) 0.0045(5) -0.0092(5) N5 0.0202(4) 0.0146(4) 0.0190(4) -0.0018(3) 0.0025(3) -0.0052(3) N6 0.0145(4) 0.0161(4) 0.0185(4) -0.0032(3) 0.0012(3) -0.0024(3) C35 0.0151(5) 0.0157(5) 0.0168(5) -0.0021(4) -0.0004(4) -0.0033(4) C36 0.0133(5) 0.0186(5) 0.0188(5) -0.0025(4) 0.0007(4) -0.0041(4) C37 0.0192(5) 0.0225(5) 0.0205(5) 0.0022(4) 0.0018(4) -0.0058(4) C38 0.0194(5) 0.0329(6) 0.0162(5) -0.0012(4) 0.0024(4) -0.0065(5) C39 0.0185(5) 0.0286(6) 0.0189(5) -0.0080(4) 0.0021(4) -0.0033(4) C40 0.0151(5) 0.0194(5) 0.0205(5) -0.0041(4) 0.0006(4) -0.0029(4) C41 0.0127(5) 0.0182(5) 0.0157(5) -0.0011(4) -0.0001(4) -0.0027(4) C42 0.0170(5) 0.0140(5) 0.0154(5) -0.0023(4) -0.0004(4) -0.0026(4) C43 0.0211(5) 0.0184(5) 0.0119(5) -0.0021(4) 0.0005(4) -0.0054(4) C44 0.0290(6) 0.0183(5) 0.0172(5) -0.0026(4) 0.0033(4) -0.0050(4) C45 0.0392(7) 0.0222(6) 0.0215(6) -0.0036(4) 0.0068(5) -0.0155(5) C46 0.0289(6) 0.0317(6) 0.0195(5) -0.0054(5) 0.0069(5) -0.0171(5) C47 0.0205(5) 0.0264(6) 0.0160(5) -0.0043(4) 0.0032(4) -0.0072(4) C48 0.0208(5) 0.0189(5) 0.0115(5) -0.0022(4) 0.0002(4) -0.0059(4) C49 0.0329(6) 0.0150(5) 0.0289(6) -0.0019(4) 0.0031(5) -0.0050(5) C50 0.0222(5) 0.0226(5) 0.0198(5) -0.0072(4) -0.0024(4) -0.0043(4) C51 0.0199(5) 0.0226(6) 0.0190(5) -0.0018(4) -0.0024(4) 0.0004(4) N7 0.0193(5) 0.0211(5) 0.0226(5) 0.0009(4) -0.0022(4) -0.0066(4) N8 0.0182(5) 0.0282(5) 0.0256(5) -0.0068(4) -0.0071(4) -0.0034(4) C52 0.0177(5) 0.0178(5) 0.0226(5) -0.0005(4) -0.0032(4) -0.0046(4) C53 0.0210(5) 0.0156(5) 0.0223(5) -0.0052(4) -0.0023(4) -0.0005(4) C54 0.0321(6) 0.0218(6) 0.0219(6) -0.0039(4) -0.0006(5) -0.0013(5) C55 0.0379(7) 0.0316(7) 0.0238(6) -0.0090(5) -0.0108(5) 0.0038(6) C56 0.0256(6) 0.0363(7) 0.0350(7) -0.0159(6) -0.0119(5) -0.0003(5) C57 0.0201(6) 0.0279(6) 0.0330(6) -0.0127(5) -0.0017(5) -0.0036(5) C58 0.0181(5) 0.0172(5) 0.0226(5) -0.0066(4) -0.0021(4) -0.0006(4) C59 0.0176(5) 0.0159(5) 0.0231(5) -0.0018(4) -0.0020(4) -0.0051(4) C60 0.0229(5) 0.0171(5) 0.0158(5) 0.0018(4) -0.0008(4) -0.0077(4) C61 0.0220(6) 0.0278(6) 0.0215(5) -0.0020(4) 0.0017(4) -0.0105(5) C62 0.0256(6) 0.0295(6) 0.0230(6) -0.0026(5) 0.0068(5) -0.0066(5) C63 0.0362(7) 0.0214(6) 0.0156(5) -0.0004(4) 0.0031(5) -0.0083(5) C64 0.0292(6) 0.0209(5) 0.0175(5) 0.0018(4) -0.0052(4) -0.0090(5) C65 0.0220(5) 0.0171(5) 0.0178(5) 0.0038(4) -0.0038(4) -0.0060(4) C66 0.0231(6) 0.0332(7) 0.0314(6) 0.0019(5) 0.0027(5) -0.0098(5) C67 0.0219(6) 0.0234(6) 0.0314(6) -0.0015(5) -0.0022(5) 0.0000(5) C68 0.0306(6) 0.0201(6) 0.0355(7) -0.0004(5) 0.0010(5) -0.0108(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 1.3927(13) . ? N1 C15 1.4509(14) . ? N1 C1 1.4645(13) . ? N2 C14 1.4048(13) . ? N2 C1 1.4967(13) . ? N2 H1N 0.893(14) . ? C1 C16 1.5195(14) . ? C1 C8 1.5769(14) . ? C2 C3 1.3893(15) . ? C2 C7 1.3975(15) . ? C3 C4 1.3970(16) . ? C3 H3 0.9500 . ? C4 C5 1.3881(17) . ? C4 H4 0.9500 . ? C5 C6 1.3985(15) . ? C5 H5 0.9500 . ? C6 C7 1.3777(15) . ? C6 H6 0.9500 . ? C7 C8 1.5191(14) . ? C8 C9 1.5096(15) . ? C8 C17 1.5295(14) . ? C9 C10 1.3867(15) . ? C9 C14 1.3928(15) . ? C10 C11 1.3945(18) . ? C10 H10 0.9500 . ? C11 C12 1.390(2) . ? C11 H11 0.9500 . ? C12 C13 1.3921(17) . ? C12 H12 0.9500 . ? C13 C14 1.3893(16) . ? C13 H13 0.9500 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? N3 C19 1.3826(14) . ? N3 C32 1.4457(15) . ? N3 C18 1.4725(14) . ? N4 C31 1.3960(16) . ? N4 C18 1.4870(14) . ? N4 H2N 0.896(15) . ? C18 C33 1.5165(15) . ? C18 C25 1.5831(15) . ? C19 C24 1.3954(15) . ? C19 C20 1.3968(15) . ? C20 C21 1.3908(17) . ? C20 H20 0.9500 . ? C21 C22 1.3836(19) . ? C21 H21 0.9500 . ? C22 C23 1.3990(17) . ? C22 H22 0.9500 . ? C23 C24 1.3789(15) . ? C23 H23 0.9500 . ? C24 C25 1.5210(14) . ? C25 C26 1.5131(15) . ? C25 C34 1.5295(15) . ? C26 C27 1.3837(17) . ? C26 C31 1.3960(16) . ? C27 C28 1.3962(18) . ? C27 H27 0.9500 . ? C28 C29 1.384(2) . ? C28 H28 0.9500 . ? C29 C30 1.394(2) . ? C29 H29 0.9500 . ? C30 C31 1.3939(16) . ? C30 H30 0.9500 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? N5 C36 1.3941(14) . ? N5 C49 1.4561(14) . ? N5 C35 1.4652(13) . ? N6 C48 1.3991(14) . ? N6 C35 1.4923(13) . ? N6 H3N 0.899(14) . ? C35 C50 1.5213(14) . ? C35 C42 1.5751(14) . ? C36 C37 1.3905(15) . ? C36 C41 1.3981(15) . ? C37 C38 1.3980(17) . ? C37 H37 0.9500 . ? C38 C39 1.3857(17) . ? C38 H38 0.9500 . ? C39 C40 1.4012(16) . ? C39 H39 0.9500 . ? C40 C41 1.3788(15) . ? C40 H40 0.9500 . ? C41 C42 1.5219(14) . ? C42 C43 1.5139(15) . ? C42 C51 1.5297(14) . ? C43 C44 1.3828(15) . ? C43 C48 1.3982(15) . ? C44 C45 1.3989(17) . ? C44 H44 0.9500 . ? C45 C46 1.3908(19) . ? C45 H45 0.9500 . ? C46 C47 1.3953(17) . ? C46 H46 0.9500 . ? C47 C48 1.3923(15) . ? C47 H47 0.9500 . ? C49 H49A 0.9800 . ? C49 H49B 0.9800 . ? C49 H49C 0.9800 . ? C50 H50A 0.9800 . ? C50 H50B 0.9800 . ? C50 H50C 0.9800 . ? C51 H51A 0.9800 . ? C51 H51B 0.9800 . ? C51 H51C 0.9800 . ? N7 C53 1.3733(14) . ? N7 C66 1.4402(15) . ? N7 C52 1.4854(14) . ? N8 C65 1.3853(15) . ? N8 C52 1.4523(14) . ? N8 H4N 0.853(15) . ? C52 C67 1.5198(16) . ? C52 C59 1.5804(15) . ? C53 C54 1.3933(16) . ? C53 C58 1.4012(16) . ? C54 C55 1.4004(18) . ? C54 H54 0.9500 . ? C55 C56 1.380(2) . ? C55 H55 0.9500 . ? C56 C57 1.4053(18) . ? C56 H56 0.9500 . ? C57 C58 1.3764(16) . ? C57 H57 0.9500 . ? C58 C59 1.5115(15) . ? C59 C60 1.5265(15) . ? C59 C68 1.5300(15) . ? C60 C61 1.3807(16) . ? C60 C65 1.4016(15) . ? C61 C62 1.3983(17) . ? C61 H61 0.9500 . ? C62 C63 1.3911(17) . ? C62 H62 0.9500 . ? C63 C64 1.3916(18) . ? C63 H63 0.9500 . ? C64 C65 1.3932(16) . ? C64 H64 0.9500 . ? C66 H66A 0.9800 . ? C66 H66B 0.9800 . ? C66 H66C 0.9800 . ? C67 H67A 0.9800 . ? C67 H67B 0.9800 . ? C67 H67C 0.9800 . ? C68 H68A 0.9800 . ? C68 H68B 0.9800 . ? C68 H68C 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 C2 N1 C15 119.14(9) . . ? C2 N1 C1 108.28(8) . . ? C15 N1 C1 119.47(9) . . ? C14 N2 C1 108.67(8) . . ? C14 N2 H1N 115.3(9) . . ? C1 N2 H1N 113.7(9) . . ? N1 C1 N2 111.63(8) . . ? N1 C1 C16 111.40(9) . . ? N2 C1 C16 110.62(9) . . ? N1 C1 C8 103.98(8) . . ? N2 C1 C8 102.92(8) . . ? C16 C1 C8 115.89(8) . . ? C3 C2 N1 128.64(10) . . ? C3 C2 C7 120.61(10) . . ? N1 C2 C7 110.74(9) . . ? C2 C3 C4 117.99(10) . . ? C2 C3 H3 121.0 . . ? C4 C3 H3 121.0 . . ? C5 C4 C3 121.46(10) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? C4 C5 C6 120.01(10) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C7 C6 C5 118.81(10) . . ? C7 C6 H6 120.6 . . ? C5 C6 H6 120.6 . . ? C6 C7 C2 121.11(10) . . ? C6 C7 C8 129.60(10) . . ? C2 C7 C8 109.29(9) . . ? C9 C8 C7 110.74(8) . . ? C9 C8 C17 114.41(9) . . ? C7 C8 C17 111.16(9) . . ? C9 C8 C1 102.94(8) . . ? C7 C8 C1 101.11(8) . . ? C17 C8 C1 115.47(9) . . ? C10 C9 C14 120.26(11) . . ? C10 C9 C8 130.23(10) . . ? C14 C9 C8 109.33(9) . . ? C9 C10 C11 118.88(11) . . ? C9 C10 H10 120.6 . . ? C11 C10 H10 120.6 . . ? C12 C11 C10 120.36(11) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C11 C12 C13 121.20(12) . . ? C11 C12 H12 119.4 . . ? C13 C12 H12 119.4 . . ? C14 C13 C12 117.88(11) . . ? C14 C13 H13 121.1 . . ? C12 C13 H13 121.1 . . ? C13 C14 C9 121.41(10) . . ? C13 C14 N2 127.18(10) . . ? C9 C14 N2 111.26(9) . . ? N1 C15 H15A 109.5 . . ? N1 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N1 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C1 C16 H16A 109.5 . . ? C1 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C1 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C8 C17 H17A 109.5 . . ? C8 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C8 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C19 N3 C32 119.99(10) . . ? C19 N3 C18 109.50(9) . . ? C32 N3 C18 119.26(10) . . ? C31 N4 C18 109.34(9) . . ? C31 N4 H2N 117.7(9) . . ? C18 N4 H2N 113.8(9) . . ? N3 C18 N4 112.06(9) . . ? N3 C18 C33 109.55(9) . . ? N4 C18 C33 110.83(9) . . ? N3 C18 C25 104.21(8) . . ? N4 C18 C25 103.59(9) . . ? C33 C18 C25 116.39(9) . . ? N3 C19 C24 111.28(9) . . ? N3 C19 C20 128.09(10) . . ? C24 C19 C20 120.59(10) . . ? C21 C20 C19 118.08(11) . . ? C21 C20 H20 121.0 . . ? C19 C20 H20 121.0 . . ? C22 C21 C20 121.64(11) . . ? C22 C21 H21 119.2 . . ? C20 C21 H21 119.2 . . ? C21 C22 C23 119.75(11) . . ? C21 C22 H22 120.1 . . ? C23 C22 H22 120.1 . . ? C24 C23 C22 119.36(11) . . ? C24 C23 H23 120.3 . . ? C22 C23 H23 120.3 . . ? C23 C24 C19 120.57(10) . . ? C23 C24 C25 129.84(10) . . ? C19 C24 C25 109.59(9) . . ? C26 C25 C24 112.31(9) . . ? C26 C25 C34 112.80(9) . . ? C24 C25 C34 110.86(9) . . ? C26 C25 C18 102.97(8) . . ? C24 C25 C18 101.64(8) . . ? C34 C25 C18 115.60(9) . . ? C27 C26 C31 120.85(11) . . ? C27 C26 C25 129.83(11) . . ? C31 C26 C25 109.30(10) . . ? C26 C27 C28 118.88(13) . . ? C26 C27 H27 120.6 . . ? C28 C27 H27 120.6 . . ? C29 C28 C27 120.26(13) . . ? C29 C28 H28 119.9 . . ? C27 C28 H28 119.9 . . ? C28 C29 C30 121.27(11) . . ? C28 C29 H29 119.4 . . ? C30 C29 H29 119.4 . . ? C31 C30 C29 118.32(13) . . ? C31 C30 H30 120.8 . . ? C29 C30 H30 120.8 . . ? C30 C31 N4 127.99(12) . . ? C30 C31 C26 120.40(12) . . ? N4 C31 C26 111.57(10) . . ? N3 C32 H32A 109.5 . . ? N3 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? N3 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C18 C33 H33A 109.5 . . ? C18 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C18 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C25 C34 H34A 109.5 . . ? C25 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C25 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C36 N5 C49 119.15(9) . . ? C36 N5 C35 107.61(8) . . ? C49 N5 C35 118.76(9) . . ? C48 N6 C35 108.47(8) . . ? C48 N6 H3N 114.6(9) . . ? C35 N6 H3N 116.4(9) . . ? N5 C35 N6 111.45(8) . . ? N5 C35 C50 111.73(9) . . ? N6 C35 C50 111.27(9) . . ? N5 C35 C42 104.11(8) . . ? N6 C35 C42 102.19(8) . . ? C50 C35 C42 115.56(9) . . ? C37 C36 N5 128.27(10) . . ? C37 C36 C41 120.85(10) . . ? N5 C36 C41 110.85(9) . . ? C36 C37 C38 117.85(10) . . ? C36 C37 H37 121.1 . . ? C38 C37 H37 121.1 . . ? C39 C38 C37 121.56(10) . . ? C39 C38 H38 119.2 . . ? C37 C38 H38 119.2 . . ? C38 C39 C40 119.94(10) . . ? C38 C39 H39 120.0 . . ? C40 C39 H39 120.0 . . ? C41 C40 C39 118.99(10) . . ? C41 C40 H40 120.5 . . ? C39 C40 H40 120.5 . . ? C40 C41 C36 120.78(10) . . ? C40 C41 C42 130.02(10) . . ? C36 C41 C42 109.17(9) . . ? C43 C42 C41 112.39(8) . . ? C43 C42 C51 114.95(9) . . ? C41 C42 C51 110.29(9) . . ? C43 C42 C35 102.39(8) . . ? C41 C42 C35 100.52(8) . . ? C51 C42 C35 115.25(8) . . ? C44 C43 C48 120.22(10) . . ? C44 C43 C42 130.87(10) . . ? C48 C43 C42 108.86(9) . . ? C43 C44 C45 119.20(11) . . ? C43 C44 H44 120.4 . . ? C45 C44 H44 120.4 . . ? C46 C45 C44 119.96(11) . . ? C46 C45 H45 120.0 . . ? C44 C45 H45 120.0 . . ? C45 C46 C47 121.59(11) . . ? C45 C46 H46 119.2 . . ? C47 C46 H46 119.2 . . ? C48 C47 C46 117.59(11) . . ? C48 C47 H47 121.2 . . ? C46 C47 H47 121.2 . . ? C47 C48 C43 121.44(10) . . ? C47 C48 N6 127.69(10) . . ? C43 C48 N6 110.80(9) . . ? N5 C49 H49A 109.5 . . ? N5 C49 H49B 109.5 . . ? H49A C49 H49B 109.5 . . ? N5 C49 H49C 109.5 . . ? H49A C49 H49C 109.5 . . ? H49B C49 H49C 109.5 . . ? C35 C50 H50A 109.5 . . ? C35 C50 H50B 109.5 . . ? H50A C50 H50B 109.5 . . ? C35 C50 H50C 109.5 . . ? H50A C50 H50C 109.5 . . ? H50B C50 H50C 109.5 . . ? C42 C51 H51A 109.5 . . ? C42 C51 H51B 109.5 . . ? H51A C51 H51B 109.5 . . ? C42 C51 H51C 109.5 . . ? H51A C51 H51C 109.5 . . ? H51B C51 H51C 109.5 . . ? C53 N7 C66 122.38(10) . . ? C53 N7 C52 110.90(9) . . ? C66 N7 C52 121.71(9) . . ? C65 N8 C52 110.49(9) . . ? C65 N8 H4N 120.7(10) . . ? C52 N8 H4N 123.7(10) . . ? N8 C52 N7 109.79(9) . . ? N8 C52 C67 111.58(9) . . ? N7 C52 C67 111.30(10) . . ? N8 C52 C59 105.26(9) . . ? N7 C52 C59 101.40(8) . . ? C67 C52 C59 116.86(9) . . ? N7 C53 C54 128.63(11) . . ? N7 C53 C58 110.49(10) . . ? C54 C53 C58 120.85(11) . . ? C53 C54 C55 117.67(12) . . ? C53 C54 H54 121.2 . . ? C55 C54 H54 121.2 . . ? C56 C55 C54 121.76(12) . . ? C56 C55 H55 119.1 . . ? C54 C55 H55 119.1 . . ? C55 C56 C57 119.94(11) . . ? C55 C56 H56 120.0 . . ? C57 C56 H56 120.0 . . ? C58 C57 C56 119.04(12) . . ? C58 C57 H57 120.5 . . ? C56 C57 H57 120.5 . . ? C57 C58 C53 120.73(11) . . ? C57 C58 C59 130.46(11) . . ? C53 C58 C59 108.80(9) . . ? C58 C59 C60 113.78(9) . . ? C58 C59 C68 113.98(9) . . ? C60 C59 C68 109.55(9) . . ? C58 C59 C52 103.18(9) . . ? C60 C59 C52 100.93(8) . . ? C68 C59 C52 114.67(9) . . ? C61 C60 C65 120.76(11) . . ? C61 C60 C59 129.82(10) . . ? C65 C60 C59 109.34(10) . . ? C60 C61 C62 119.17(11) . . ? C60 C61 H61 120.4 . . ? C62 C61 H61 120.4 . . ? C63 C62 C61 119.79(11) . . ? C63 C62 H62 120.1 . . ? C61 C62 H62 120.1 . . ? C62 C63 C64 121.51(11) . . ? C62 C63 H63 119.2 . . ? C64 C63 H63 119.2 . . ? C63 C64 C65 118.28(10) . . ? C63 C64 H64 120.9 . . ? C65 C64 H64 120.9 . . ? N8 C65 C64 128.71(10) . . ? N8 C65 C60 110.87(10) . . ? C64 C65 C60 120.41(11) . . ? N7 C66 H66A 109.5 . . ? N7 C66 H66B 109.5 . . ? H66A C66 H66B 109.5 . . ? N7 C66 H66C 109.5 . . ? H66A C66 H66C 109.5 . . ? H66B C66 H66C 109.5 . . ? C52 C67 H67A 109.5 . . ? C52 C67 H67B 109.5 . . ? H67A C67 H67B 109.5 . . ? C52 C67 H67C 109.5 . . ? H67A C67 H67C 109.5 . . ? H67B C67 H67C 109.5 . . ? C59 C68 H68A 109.5 . . ? C59 C68 H68B 109.5 . . ? H68A C68 H68B 109.5 . . ? C59 C68 H68C 109.5 . . ? H68A C68 H68C 109.5 . . ? H68B C68 H68C 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 C2 N1 C1 N2 -84.26(10) . . . . ? C15 N1 C1 N2 56.61(12) . . . . ? C2 N1 C1 C16 151.53(9) . . . . ? C15 N1 C1 C16 -67.60(12) . . . . ? C2 N1 C1 C8 26.02(10) . . . . ? C15 N1 C1 C8 166.88(9) . . . . ? C14 N2 C1 N1 132.41(9) . . . . ? C14 N2 C1 C16 -102.94(10) . . . . ? C14 N2 C1 C8 21.46(10) . . . . ? C15 N1 C2 C3 21.11(16) . . . . ? C1 N1 C2 C3 162.12(10) . . . . ? C15 N1 C2 C7 -160.21(9) . . . . ? C1 N1 C2 C7 -19.20(11) . . . . ? N1 C2 C3 C4 178.41(10) . . . . ? C7 C2 C3 C4 -0.15(15) . . . . ? C2 C3 C4 C5 -0.73(16) . . . . ? C3 C4 C5 C6 0.55(17) . . . . ? C4 C5 C6 C7 0.53(16) . . . . ? C5 C6 C7 C2 -1.42(16) . . . . ? C5 C6 C7 C8 177.45(10) . . . . ? C3 C2 C7 C6 1.25(16) . . . . ? N1 C2 C7 C6 -177.55(9) . . . . ? C3 C2 C7 C8 -177.84(9) . . . . ? N1 C2 C7 C8 3.36(12) . . . . ? C6 C7 C8 C9 -58.19(14) . . . . ? C2 C7 C8 C9 120.79(9) . . . . ? C6 C7 C8 C17 70.15(14) . . . . ? C2 C7 C8 C17 -110.87(10) . . . . ? C6 C7 C8 C1 -166.76(10) . . . . ? C2 C7 C8 C1 12.22(11) . . . . ? N1 C1 C8 C9 -137.03(8) . . . . ? N2 C1 C8 C9 -20.48(9) . . . . ? C16 C1 C8 C9 100.37(10) . . . . ? N1 C1 C8 C7 -22.48(10) . . . . ? N2 C1 C8 C7 94.06(9) . . . . ? C16 C1 C8 C7 -145.08(9) . . . . ? N1 C1 C8 C17 97.59(10) . . . . ? N2 C1 C8 C17 -145.87(9) . . . . ? C16 C1 C8 C17 -25.02(13) . . . . ? C7 C8 C9 C10 81.12(14) . . . . ? C17 C8 C9 C10 -45.43(15) . . . . ? C1 C8 C9 C10 -171.51(11) . . . . ? C7 C8 C9 C14 -93.97(10) . . . . ? C17 C8 C9 C14 139.48(9) . . . . ? C1 C8 C9 C14 13.40(11) . . . . ? C14 C9 C10 C11 -0.25(16) . . . . ? C8 C9 C10 C11 -174.88(11) . . . . ? C9 C10 C11 C12 0.19(18) . . . . ? C10 C11 C12 C13 0.17(19) . . . . ? C11 C12 C13 C14 -0.46(18) . . . . ? C12 C13 C14 C9 0.40(16) . . . . ? C12 C13 C14 N2 175.58(10) . . . . ? C10 C9 C14 C13 -0.06(16) . . . . ? C8 C9 C14 C13 175.60(9) . . . . ? C10 C9 C14 N2 -175.93(9) . . . . ? C8 C9 C14 N2 -0.27(12) . . . . ? C1 N2 C14 C13 170.31(10) . . . . ? C1 N2 C14 C9 -14.11(11) . . . . ? C19 N3 C18 N4 -91.60(11) . . . . ? C32 N3 C18 N4 52.13(14) . . . . ? C19 N3 C18 C33 144.96(9) . . . . ? C32 N3 C18 C33 -71.31(13) . . . . ? C19 N3 C18 C25 19.76(11) . . . . ? C32 N3 C18 C25 163.49(10) . . . . ? C31 N4 C18 N3 129.66(10) . . . . ? C31 N4 C18 C33 -107.62(11) . . . . ? C31 N4 C18 C25 17.92(11) . . . . ? C32 N3 C19 C24 -157.94(11) . . . . ? C18 N3 C19 C24 -14.51(12) . . . . ? C32 N3 C19 C20 24.31(17) . . . . ? C18 N3 C19 C20 167.74(10) . . . . ? N3 C19 C20 C21 177.13(11) . . . . ? C24 C19 C20 C21 -0.43(16) . . . . ? C19 C20 C21 C22 -0.10(17) . . . . ? C20 C21 C22 C23 0.30(19) . . . . ? C21 C22 C23 C24 0.03(18) . . . . ? C22 C23 C24 C19 -0.55(17) . . . . ? C22 C23 C24 C25 -179.95(11) . . . . ? N3 C19 C24 C23 -177.18(10) . . . . ? C20 C19 C24 C23 0.76(16) . . . . ? N3 C19 C24 C25 2.33(12) . . . . ? C20 C19 C24 C25 -179.73(9) . . . . ? C23 C24 C25 C26 -61.62(15) . . . . ? C19 C24 C25 C26 118.93(10) . . . . ? C23 C24 C25 C34 65.57(15) . . . . ? C19 C24 C25 C34 -113.87(10) . . . . ? C23 C24 C25 C18 -171.02(11) . . . . ? C19 C24 C25 C18 9.53(11) . . . . ? N3 C18 C25 C26 -133.51(8) . . . . ? N4 C18 C25 C26 -16.13(10) . . . . ? C33 C18 C25 C26 105.77(10) . . . . ? N3 C18 C25 C24 -17.08(10) . . . . ? N4 C18 C25 C24 100.30(9) . . . . ? C33 C18 C25 C24 -137.80(9) . . . . ? N3 C18 C25 C34 103.04(10) . . . . ? N4 C18 C25 C34 -139.58(9) . . . . ? C33 C18 C25 C34 -17.68(13) . . . . ? C24 C25 C26 C27 79.78(14) . . . . ? C34 C25 C26 C27 -46.37(15) . . . . ? C18 C25 C26 C27 -171.66(11) . . . . ? C24 C25 C26 C31 -98.99(10) . . . . ? C34 C25 C26 C31 134.85(10) . . . . ? C18 C25 C26 C31 9.56(11) . . . . ? C31 C26 C27 C28 -0.66(17) . . . . ? C25 C26 C27 C28 -179.31(11) . . . . ? C26 C27 C28 C29 -0.27(18) . . . . ? C27 C28 C29 C30 1.26(19) . . . . ? C28 C29 C30 C31 -1.28(18) . . . . ? C29 C30 C31 N4 178.16(11) . . . . ? C29 C30 C31 C26 0.33(17) . . . . ? C18 N4 C31 C30 169.22(11) . . . . ? C18 N4 C31 C26 -12.80(13) . . . . ? C27 C26 C31 C30 0.63(16) . . . . ? C25 C26 C31 C30 179.54(10) . . . . ? C27 C26 C31 N4 -177.52(10) . . . . ? C25 C26 C31 N4 1.38(12) . . . . ? C36 N5 C35 N6 81.52(10) . . . . ? C49 N5 C35 N6 -57.68(12) . . . . ? C36 N5 C35 C50 -153.30(9) . . . . ? C49 N5 C35 C50 67.50(12) . . . . ? C36 N5 C35 C42 -27.91(10) . . . . ? C49 N5 C35 C42 -167.12(9) . . . . ? C48 N6 C35 N5 -137.03(9) . . . . ? C48 N6 C35 C50 97.53(10) . . . . ? C48 N6 C35 C42 -26.36(10) . . . . ? C49 N5 C36 C37 -23.52(16) . . . . ? C35 N5 C36 C37 -162.53(11) . . . . ? C49 N5 C36 C41 158.69(10) . . . . ? C35 N5 C36 C41 19.67(11) . . . . ? N5 C36 C37 C38 -175.71(10) . . . . ? C41 C36 C37 C38 1.89(16) . . . . ? C36 C37 C38 C39 -0.78(17) . . . . ? C37 C38 C39 C40 -0.22(17) . . . . ? C38 C39 C40 C41 0.13(16) . . . . ? C39 C40 C41 C36 0.98(15) . . . . ? C39 C40 C41 C42 178.81(10) . . . . ? C37 C36 C41 C40 -2.03(16) . . . . ? N5 C36 C41 C40 175.95(9) . . . . ? C37 C36 C41 C42 179.73(9) . . . . ? N5 C36 C41 C42 -2.28(12) . . . . ? C40 C41 C42 C43 59.47(14) . . . . ? C36 C41 C42 C43 -122.51(10) . . . . ? C40 C41 C42 C51 -70.23(14) . . . . ? C36 C41 C42 C51 107.79(10) . . . . ? C40 C41 C42 C35 167.68(11) . . . . ? C36 C41 C42 C35 -14.30(10) . . . . ? N5 C35 C42 C43 140.83(8) . . . . ? N6 C35 C42 C43 24.72(9) . . . . ? C50 C35 C42 C43 -96.26(10) . . . . ? N5 C35 C42 C41 24.89(10) . . . . ? N6 C35 C42 C41 -91.22(9) . . . . ? C50 C35 C42 C41 147.80(9) . . . . ? N5 C35 C42 C51 -93.64(10) . . . . ? N6 C35 C42 C51 150.25(9) . . . . ? C50 C35 C42 C51 29.28(13) . . . . ? C41 C42 C43 C44 -86.00(14) . . . . ? C51 C42 C43 C44 41.25(15) . . . . ? C35 C42 C43 C44 166.98(11) . . . . ? C41 C42 C43 C48 91.19(10) . . . . ? C51 C42 C43 C48 -141.55(9) . . . . ? C35 C42 C43 C48 -15.82(11) . . . . ? C48 C43 C44 C45 -0.17(16) . . . . ? C42 C43 C44 C45 176.75(10) . . . . ? C43 C44 C45 C46 0.01(17) . . . . ? C44 C45 C46 C47 0.29(18) . . . . ? C45 C46 C47 C48 -0.40(17) . . . . ? C46 C47 C48 C43 0.23(16) . . . . ? C46 C47 C48 N6 -176.50(10) . . . . ? C44 C43 C48 C47 0.05(16) . . . . ? C42 C43 C48 C47 -177.50(9) . . . . ? C44 C43 C48 N6 177.29(9) . . . . ? C42 C43 C48 N6 -0.26(12) . . . . ? C35 N6 C48 C47 -165.31(10) . . . . ? C35 N6 C48 C43 17.66(11) . . . . ? C65 N8 C52 N7 94.14(11) . . . . ? C65 N8 C52 C67 -141.98(10) . . . . ? C65 N8 C52 C59 -14.27(12) . . . . ? C53 N7 C52 N8 -133.64(10) . . . . ? C66 N7 C52 N8 70.86(13) . . . . ? C53 N7 C52 C67 102.31(11) . . . . ? C66 N7 C52 C67 -53.18(14) . . . . ? C53 N7 C52 C59 -22.67(11) . . . . ? C66 N7 C52 C59 -178.17(10) . . . . ? C66 N7 C53 C54 -11.08(18) . . . . ? C52 N7 C53 C54 -166.38(11) . . . . ? C66 N7 C53 C58 171.00(10) . . . . ? C52 N7 C53 C58 15.70(13) . . . . ? N7 C53 C54 C55 -177.15(11) . . . . ? C58 C53 C54 C55 0.58(17) . . . . ? C53 C54 C55 C56 -0.65(18) . . . . ? C54 C55 C56 C57 0.2(2) . . . . ? C55 C56 C57 C58 0.29(18) . . . . ? C56 C57 C58 C53 -0.35(17) . . . . ? C56 C57 C58 C59 178.05(11) . . . . ? N7 C53 C58 C57 178.02(10) . . . . ? C54 C53 C58 C57 -0.09(17) . . . . ? N7 C53 C58 C59 -0.70(13) . . . . ? C54 C53 C58 C59 -178.81(10) . . . . ? C57 C58 C59 C60 -83.21(15) . . . . ? C53 C58 C59 C60 95.35(11) . . . . ? C57 C58 C59 C68 43.39(17) . . . . ? C53 C58 C59 C68 -138.05(10) . . . . ? C57 C58 C59 C52 168.38(12) . . . . ? C53 C58 C59 C52 -13.07(11) . . . . ? N8 C52 C59 C58 134.97(9) . . . . ? N7 C52 C59 C58 20.58(10) . . . . ? C67 C52 C59 C58 -100.59(11) . . . . ? N8 C52 C59 C60 17.13(10) . . . . ? N7 C52 C59 C60 -97.26(9) . . . . ? C67 C52 C59 C60 141.57(10) . . . . ? N8 C52 C59 C68 -100.50(11) . . . . ? N7 C52 C59 C68 145.11(10) . . . . ? C67 C52 C59 C68 23.94(14) . . . . ? C58 C59 C60 C61 58.66(15) . . . . ? C68 C59 C60 C61 -70.22(15) . . . . ? C52 C59 C60 C61 168.47(11) . . . . ? C58 C59 C60 C65 -124.81(10) . . . . ? C68 C59 C60 C65 106.31(10) . . . . ? C52 C59 C60 C65 -15.00(11) . . . . ? C65 C60 C61 C62 -0.73(17) . . . . ? C59 C60 C61 C62 175.46(11) . . . . ? C60 C61 C62 C63 -1.77(17) . . . . ? C61 C62 C63 C64 2.03(18) . . . . ? C62 C63 C64 C65 0.25(17) . . . . ? C52 N8 C65 C64 -173.85(11) . . . . ? C52 N8 C65 C60 4.81(13) . . . . ? C63 C64 C65 N8 175.78(11) . . . . ? C63 C64 C65 C60 -2.77(16) . . . . ? C61 C60 C65 N8 -175.74(10) . . . . ? C59 C60 C65 N8 7.36(12) . . . . ? C61 C60 C65 C64 3.05(16) . . . . ? C59 C60 C65 C64 -173.85(10) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.58 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.357 _refine_diff_density_min -0.240 _refine_diff_density_rms 0.042 # Attachment '2.cif' data_rs12116512 _database_code_depnum_ccdc_archive 'CCDC 789829' #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H16 N2 O' _chemical_formula_sum 'C16 H16 N2 O' _chemical_formula_weight 252.31 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.3998(16) _cell_length_b 8.7381(7) _cell_length_c 14.9479(10) _cell_angle_alpha 90.00 _cell_angle_beta 123.196(4) _cell_angle_gamma 90.00 _cell_volume 2557.6(3) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2.55 _cell_measurement_theta_min 22.25 _cell_measurement_theta_max 1701 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6306 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details 'SADABS V2008/1' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker APex II Kappa with CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 19772 _diffrn_reflns_av_R_equivalents 0.0815 _diffrn_reflns_av_sigmaI/netI 0.0487 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2614 _reflns_number_gt 1770 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex II' _computing_cell_refinement 'Bruker Apex II' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0441P)^2^+1.3247P] 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 2614 _refine_ls_number_parameters 180 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0778 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.1050 _refine_ls_wR_factor_gt 0.0892 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _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 0.26025(7) -0.00863(16) 0.36551(11) 0.0218(4) Uani 1 1 d . . . N2 N 0.13586(8) 0.00043(19) 0.11022(13) 0.0253(4) Uani 1 1 d . . . H1 H 0.1201(11) -0.042(2) 0.0492(18) 0.038 Uiso 1 1 d . . . H2 H 0.1568(11) -0.070(2) 0.1643(17) 0.038 Uiso 1 1 d . . . O1 O 0.24914(6) 0.25161(13) 0.33491(10) 0.0242(3) Uani 1 1 d . . . C1 C 0.22565(9) 0.12722(19) 0.33644(13) 0.0194(4) Uani 1 1 d . . . C2 C 0.15321(8) 0.09805(19) 0.31224(13) 0.0185(4) Uani 1 1 d . . . C3 C 0.15319(9) -0.07504(19) 0.32139(13) 0.0202(4) Uani 1 1 d . . . C4 C 0.10195(10) -0.1742(2) 0.30247(14) 0.0258(4) Uani 1 1 d . . . H4 H 0.0579 -0.1370 0.2802 0.031 Uiso 1 1 calc R . . C5 C 0.11614(10) -0.3307(2) 0.31667(15) 0.0321(5) Uani 1 1 d . . . H5 H 0.0816 -0.4009 0.3046 0.038 Uiso 1 1 calc R . . C6 C 0.18041(11) -0.3844(2) 0.34833(15) 0.0319(5) Uani 1 1 d . . . H6 H 0.1888 -0.4915 0.3561 0.038 Uiso 1 1 calc R . . C7 C 0.23266(10) -0.2857(2) 0.36887(15) 0.0275(4) Uani 1 1 d . . . H7 H 0.2768 -0.3227 0.3917 0.033 Uiso 1 1 calc R . . C8 C 0.21773(9) -0.13067(19) 0.35476(13) 0.0211(4) Uani 1 1 d . . . C9 C 0.33063(9) -0.0267(2) 0.39585(16) 0.0291(5) Uani 1 1 d . . . H9A H 0.3500 0.0740 0.3986 0.044 Uiso 1 1 calc R . . H9B H 0.3317 -0.0910 0.3430 0.044 Uiso 1 1 calc R . . H9C H 0.3576 -0.0752 0.4664 0.044 Uiso 1 1 calc R . . C10 C 0.15259(9) 0.1698(2) 0.40572(13) 0.0234(4) Uani 1 1 d . . . H10A H 0.1077 0.1539 0.3949 0.035 Uiso 1 1 calc R . . H10B H 0.1618 0.2798 0.4089 0.035 Uiso 1 1 calc R . . H10C H 0.1879 0.1214 0.4729 0.035 Uiso 1 1 calc R . . C11 C 0.09766(8) 0.16070(19) 0.20245(13) 0.0187(4) Uani 1 1 d . . . C12 C 0.09086(8) 0.1062(2) 0.10855(14) 0.0204(4) Uani 1 1 d . . . C13 C 0.03945(9) 0.1675(2) 0.00959(14) 0.0250(4) Uani 1 1 d . . . H13 H 0.0344 0.1302 -0.0541 0.030 Uiso 1 1 calc R . . C14 C -0.00379(9) 0.2805(2) 0.00299(16) 0.0279(4) Uani 1 1 d . . . H14 H -0.0382 0.3207 -0.0647 0.033 Uiso 1 1 calc R . . C15 C 0.00295(9) 0.3354(2) 0.09501(15) 0.0281(4) Uani 1 1 d . . . H15 H -0.0265 0.4138 0.0911 0.034 Uiso 1 1 calc R . . C16 C 0.05321(9) 0.2748(2) 0.19322(15) 0.0233(4) Uani 1 1 d . . . H16 H 0.0574 0.3124 0.2562 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 0.0192(7) 0.0219(8) 0.0220(8) 0.0001(6) 0.0100(6) 0.0006(6) N2 0.0268(9) 0.0288(9) 0.0185(8) -0.0034(7) 0.0113(7) 0.0014(7) O1 0.0247(7) 0.0234(7) 0.0225(7) -0.0037(5) 0.0116(6) -0.0056(5) C1 0.0213(9) 0.0218(9) 0.0119(8) -0.0036(7) 0.0070(7) -0.0012(7) C2 0.0200(9) 0.0180(9) 0.0175(9) -0.0003(7) 0.0103(7) 0.0000(7) C3 0.0224(9) 0.0208(9) 0.0150(9) 0.0001(7) 0.0087(7) 0.0003(7) C4 0.0275(10) 0.0271(10) 0.0227(10) -0.0001(8) 0.0137(8) -0.0035(8) C5 0.0417(12) 0.0251(10) 0.0302(11) -0.0005(8) 0.0202(10) -0.0098(9) C6 0.0498(13) 0.0180(10) 0.0303(11) 0.0022(8) 0.0235(10) 0.0007(9) C7 0.0340(10) 0.0243(10) 0.0244(10) 0.0019(8) 0.0161(9) 0.0064(8) C8 0.0262(9) 0.0203(9) 0.0164(9) -0.0001(7) 0.0114(8) 0.0008(7) C9 0.0198(9) 0.0326(11) 0.0301(11) -0.0005(8) 0.0106(8) 0.0027(8) C10 0.0275(9) 0.0239(9) 0.0177(9) 0.0005(7) 0.0117(8) 0.0009(8) C11 0.0174(8) 0.0187(9) 0.0186(9) -0.0007(7) 0.0088(7) -0.0036(7) C12 0.0193(9) 0.0207(9) 0.0212(9) -0.0019(7) 0.0110(8) -0.0060(7) C13 0.0263(10) 0.0282(10) 0.0177(9) -0.0008(7) 0.0101(8) -0.0057(8) C14 0.0231(9) 0.0284(10) 0.0234(10) 0.0070(8) 0.0072(8) -0.0023(8) C15 0.0248(10) 0.0251(10) 0.0312(11) 0.0053(8) 0.0132(9) 0.0030(8) C16 0.0240(9) 0.0219(9) 0.0238(10) -0.0001(7) 0.0129(8) -0.0004(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 1.367(2) . ? N1 C8 1.406(2) . ? N1 C9 1.458(2) . ? N2 C12 1.391(2) . ? N2 H1 0.86(2) . ? N2 H2 0.92(2) . ? O1 C1 1.224(2) . ? C1 C2 1.549(2) . ? C2 C3 1.519(2) . ? C2 C11 1.532(2) . ? C2 C10 1.539(2) . ? C3 C4 1.377(2) . ? C3 C8 1.393(2) . ? C4 C5 1.396(3) . ? C4 H4 0.9500 . ? C5 C6 1.388(3) . ? C5 H5 0.9500 . ? C6 C7 1.386(3) . ? C6 H6 0.9500 . ? C7 C8 1.386(2) . ? C7 H7 0.9500 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C16 1.392(2) . ? C11 C12 1.406(2) . ? C12 C13 1.405(2) . ? C13 C14 1.378(3) . ? C13 H13 0.9500 . ? C14 C15 1.382(3) . ? C14 H14 0.9500 . ? C15 C16 1.389(2) . ? C15 H15 0.9500 . ? C16 H16 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 C8 111.31(14) . . ? C1 N1 C9 124.37(15) . . ? C8 N1 C9 124.16(15) . . ? C12 N2 H1 112.7(14) . . ? C12 N2 H2 119.9(13) . . ? H1 N2 H2 111.0(19) . . ? O1 C1 N1 125.69(16) . . ? O1 C1 C2 125.96(15) . . ? N1 C1 C2 108.26(14) . . ? C3 C2 C11 114.23(14) . . ? C3 C2 C10 108.87(14) . . ? C11 C2 C10 113.76(14) . . ? C3 C2 C1 101.38(13) . . ? C11 C2 C1 111.70(14) . . ? C10 C2 C1 105.91(13) . . ? C4 C3 C8 120.32(16) . . ? C4 C3 C2 130.65(16) . . ? C8 C3 C2 109.03(15) . . ? C3 C4 C5 118.53(18) . . ? C3 C4 H4 120.7 . . ? C5 C4 H4 120.7 . . ? C6 C5 C4 120.40(18) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C7 C6 C5 121.66(18) . . ? C7 C6 H6 119.2 . . ? C5 C6 H6 119.2 . . ? C8 C7 C6 117.14(18) . . ? C8 C7 H7 121.4 . . ? C6 C7 H7 121.4 . . ? C7 C8 C3 121.94(17) . . ? C7 C8 N1 128.33(17) . . ? C3 C8 N1 109.68(15) . . ? N1 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C2 C10 H10A 109.5 . . ? C2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C16 C11 C12 118.27(16) . . ? C16 C11 C2 120.79(16) . . ? C12 C11 C2 120.93(15) . . ? N2 C12 C13 118.41(17) . . ? N2 C12 C11 122.43(16) . . ? C13 C12 C11 119.03(16) . . ? C14 C13 C12 121.37(17) . . ? C14 C13 H13 119.3 . . ? C12 C13 H13 119.3 . . ? C13 C14 C15 119.88(17) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C14 C15 C16 119.26(18) . . ? C14 C15 H15 120.4 . . ? C16 C15 H15 120.4 . . ? C15 C16 C11 122.18(18) . . ? C15 C16 H16 118.9 . . ? C11 C16 H16 118.9 . . ? 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 C8 N1 C1 O1 -177.90(16) . . . . ? C9 N1 C1 O1 -2.3(3) . . . . ? C8 N1 C1 C2 5.33(19) . . . . ? C9 N1 C1 C2 -179.08(15) . . . . ? O1 C1 C2 C3 177.35(16) . . . . ? N1 C1 C2 C3 -5.90(17) . . . . ? O1 C1 C2 C11 55.3(2) . . . . ? N1 C1 C2 C11 -127.95(15) . . . . ? O1 C1 C2 C10 -69.1(2) . . . . ? N1 C1 C2 C10 107.70(15) . . . . ? C11 C2 C3 C4 -55.2(2) . . . . ? C10 C2 C3 C4 73.2(2) . . . . ? C1 C2 C3 C4 -175.45(18) . . . . ? C11 C2 C3 C8 124.81(16) . . . . ? C10 C2 C3 C8 -106.82(16) . . . . ? C1 C2 C3 C8 4.54(18) . . . . ? C8 C3 C4 C5 -0.5(3) . . . . ? C2 C3 C4 C5 179.49(17) . . . . ? C3 C4 C5 C6 -0.5(3) . . . . ? C4 C5 C6 C7 1.3(3) . . . . ? C5 C6 C7 C8 -1.0(3) . . . . ? C6 C7 C8 C3 0.0(3) . . . . ? C6 C7 C8 N1 -176.96(17) . . . . ? C4 C3 C8 C7 0.8(3) . . . . ? C2 C3 C8 C7 -179.22(16) . . . . ? C4 C3 C8 N1 178.24(15) . . . . ? C2 C3 C8 N1 -1.8(2) . . . . ? C1 N1 C8 C7 174.91(17) . . . . ? C9 N1 C8 C7 -0.7(3) . . . . ? C1 N1 C8 C3 -2.3(2) . . . . ? C9 N1 C8 C3 -177.95(15) . . . . ? C3 C2 C11 C16 127.32(17) . . . . ? C10 C2 C11 C16 1.5(2) . . . . ? C1 C2 C11 C16 -118.35(17) . . . . ? C3 C2 C11 C12 -53.6(2) . . . . ? C10 C2 C11 C12 -179.45(15) . . . . ? C1 C2 C11 C12 60.7(2) . . . . ? C16 C11 C12 N2 175.31(16) . . . . ? C2 C11 C12 N2 -3.8(3) . . . . ? C16 C11 C12 C13 -0.5(2) . . . . ? C2 C11 C12 C13 -179.64(15) . . . . ? N2 C12 C13 C14 -175.39(17) . . . . ? C11 C12 C13 C14 0.6(3) . . . . ? C12 C13 C14 C15 -0.2(3) . . . . ? C13 C14 C15 C16 -0.4(3) . . . . ? C14 C15 C16 C11 0.5(3) . . . . ? C12 C11 C16 C15 0.0(3) . . . . ? C2 C11 C16 C15 179.09(16) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.247 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.048