# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 207/401 data_pw0291 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H18 N2' _chemical_formula_weight 286.36 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 11.8635(8) _cell_length_b 13.2643(9) _cell_length_c 18.9431(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2980.9(4) _cell_formula_units_Z 8 _cell_measurement_temperature 220(2) _cell_measurement_reflns_used 48 _cell_measurement_theta_min 20 _cell_measurement_theta_max 21 _exptl_crystal_description yellow _exptl_crystal_colour rhomb _exptl_crystal_size_max 0.59 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.276 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 0.579 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.7265 _exptl_absorpt_correction_T_max 0.8594 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 220(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method '\q\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 1.2 _diffrn_reflns_number 3806 _diffrn_reflns_av_R_equivalents 0.0161 _diffrn_reflns_av_sigmaI/netI 0.0159 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -2 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 4.67 _diffrn_reflns_theta_max 60.02 _reflns_number_total 2181 _reflns_number_gt 1987 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe DIF4' _computing_cell_refinement 'Stoe DIF4' _computing_data_reduction 'Stoe REDU4' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens 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^)+(0.0525P)^2^+1.4230P] 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 SHELXL _refine_ls_extinction_coef 0.00112(16) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2181 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0500 _refine_ls_R_factor_gt 0.0460 _refine_ls_wR_factor_ref 0.1189 _refine_ls_wR_factor_gt 0.1161 _refine_ls_goodness_of_fit_ref 1.113 _refine_ls_restrained_S_all 1.113 _refine_ls_shift/su_max 0.023 _refine_ls_shift/su_mean 0.002 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 -0.1139(2) 0.0144(2) 0.38751(14) 0.0511(6) Uani 1 1 d . . . H1 H -0.163(2) 0.0152(18) 0.3471(14) 0.061 Uiso 1 1 d . . . H1' H -0.149(2) 0.0471(19) 0.4234(14) 0.061 Uiso 1 1 d . . . C2 C -0.0852(2) -0.0932(2) 0.40984(17) 0.0668(8) Uani 1 1 d . . . H2 H -0.120(3) -0.118(2) 0.4427(16) 0.080 Uiso 1 1 d . . . H2' H -0.111(2) -0.140(2) 0.3683(16) 0.080 Uiso 1 1 d . . . C3 C 0.0415(2) -0.1001(2) 0.41263(15) 0.0573(7) Uani 1 1 d . . . H3 H 0.072(2) -0.154(2) 0.3803(14) 0.069 Uiso 1 1 d . . . H3' H 0.066(2) -0.112(2) 0.4523(15) 0.069 Uiso 1 1 d . . . C3A C 0.08277(17) 0.00050(15) 0.38789(10) 0.0380(5) Uani 1 1 d . . . C4 C 0.20680(17) 0.01878(16) 0.37749(11) 0.0387(5) Uani 1 1 d . . . H4 H 0.2511(19) -0.0343(17) 0.4019(11) 0.046 Uiso 1 1 d . . . N5 N 0.22211(14) 0.01149(14) 0.29877(9) 0.0437(5) Uani 1 1 d . . . N6 N 0.22595(13) 0.09699(15) 0.27161(8) 0.0420(5) Uani 1 1 d . . . C7 C 0.21714(16) 0.17781(16) 0.32663(10) 0.0352(5) Uani 1 1 d . . . H7 H 0.2708(18) 0.2287(16) 0.3150(11) 0.042 Uiso 1 1 d . . . C7A C 0.09959(15) 0.22099(15) 0.32209(9) 0.0330(5) Uani 1 1 d . . . C8 C 0.08849(19) 0.31767(16) 0.29408(11) 0.0427(5) Uani 1 1 d . . . H8 H 0.153(2) 0.3515(17) 0.2790(12) 0.051 Uiso 1 1 d . . . C9 C -0.0144(2) 0.36476(18) 0.28863(12) 0.0516(6) Uani 1 1 d . . . H9 H -0.018(2) 0.435(2) 0.2691(13) 0.062 Uiso 1 1 d . . . C10 C -0.1084(2) 0.31668(18) 0.31146(13) 0.0528(6) Uani 1 1 d . . . H10 H -0.184(2) 0.3510(18) 0.3093(13) 0.063 Uiso 1 1 d . . . C11 C -0.10116(17) 0.22127(18) 0.33793(11) 0.0435(5) Uani 1 1 d . . . H11 H -0.171(2) 0.1855(17) 0.3543(11) 0.052 Uiso 1 1 d . . . C11A C 0.00202(15) 0.16896(15) 0.34434(10) 0.0335(5) Uani 1 1 d . . . C11B C -0.00187(15) 0.06510(16) 0.37267(10) 0.0354(5) Uani 1 1 d . . . C12 C 0.24658(16) 0.12526(15) 0.39579(10) 0.0332(5) Uani 1 1 d . . . H12 H 0.2026(17) 0.1515(15) 0.4320(11) 0.040 Uiso 1 1 d . . . C121 C 0.36967(16) 0.12967(14) 0.41610(10) 0.0332(5) Uani 1 1 d . . . C122 C 0.39958(17) 0.13822(17) 0.48663(11) 0.0410(5) Uani 1 1 d . . . H122 H 0.341(2) 0.1440(16) 0.5218(12) 0.049 Uiso 1 1 d . . . C123 C 0.51134(18) 0.14047(19) 0.50749(12) 0.0474(6) Uani 1 1 d . . . H123 H 0.5291(19) 0.1439(18) 0.5582(13) 0.057 Uiso 1 1 d . . . C124 C 0.59571(18) 0.13359(19) 0.45784(12) 0.0487(6) Uani 1 1 d . . . H124 H 0.672(2) 0.1358(17) 0.4734(12) 0.058 Uiso 1 1 d . . . C125 C 0.56776(18) 0.12475(18) 0.38715(12) 0.0466(6) Uani 1 1 d . . . H125 H 0.626(2) 0.1173(17) 0.3535(12) 0.056 Uiso 1 1 d . . . C126 C 0.45601(17) 0.12329(17) 0.36700(11) 0.0418(5) Uani 1 1 d . . . H126 H 0.4346(19) 0.1169(16) 0.3190(12) 0.050 Uiso 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 0.0372(13) 0.0656(16) 0.0506(14) -0.0002(12) -0.0005(10) -0.0083(11) C2 0.0627(17) 0.0655(17) 0.0721(18) 0.0129(15) 0.0159(14) -0.0274(14) C3 0.0625(17) 0.0506(14) 0.0589(15) 0.0133(13) -0.0121(13) -0.0070(12) C3A 0.0375(11) 0.0410(11) 0.0354(10) -0.0006(9) -0.0039(8) -0.0051(9) C4 0.0346(11) 0.0392(11) 0.0421(11) -0.0008(9) -0.0059(9) 0.0030(9) N5 0.0310(9) 0.0541(11) 0.0459(10) -0.0126(9) -0.0030(7) 0.0041(8) N6 0.0302(9) 0.0602(12) 0.0356(9) -0.0073(8) -0.0003(7) 0.0033(8) C7 0.0289(10) 0.0435(11) 0.0332(10) 0.0006(9) 0.0011(8) -0.0010(9) C7A 0.0316(10) 0.0392(11) 0.0283(9) -0.0010(8) -0.0030(8) 0.0006(8) C8 0.0444(12) 0.0442(12) 0.0396(11) 0.0021(9) -0.0039(10) -0.0027(10) C9 0.0608(15) 0.0445(13) 0.0497(13) -0.0005(11) -0.0150(11) 0.0108(12) C10 0.0470(14) 0.0561(15) 0.0552(14) -0.0080(12) -0.0161(11) 0.0133(12) C11 0.0300(11) 0.0548(14) 0.0456(12) -0.0070(10) -0.0073(9) 0.0029(10) C11A 0.0308(10) 0.0400(11) 0.0298(9) -0.0055(8) -0.0041(8) 0.0002(8) C11B 0.0306(11) 0.0451(12) 0.0303(9) -0.0041(9) -0.0002(8) -0.0043(9) C12 0.0285(10) 0.0428(11) 0.0282(9) -0.0027(8) 0.0007(8) 0.0002(9) C121 0.0297(10) 0.0375(11) 0.0323(10) -0.0024(8) -0.0009(8) 0.0006(8) C122 0.0333(11) 0.0546(13) 0.0349(11) -0.0027(9) 0.0002(9) 0.0003(10) C123 0.0387(12) 0.0677(16) 0.0360(11) -0.0053(11) -0.0068(9) 0.0011(11) C124 0.0290(11) 0.0655(15) 0.0515(13) -0.0047(11) -0.0056(10) 0.0025(10) C125 0.0308(11) 0.0645(15) 0.0445(12) -0.0067(11) 0.0051(9) 0.0025(10) C126 0.0336(11) 0.0586(13) 0.0333(11) -0.0043(10) -0.0002(9) 0.0014(10) _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 C11B 1.516(3) . ? C1 C2 1.526(4) . ? C1 H1 0.96(3) . ? C1 H1' 0.91(3) . ? C2 C3 1.508(4) . ? C2 H2 0.81(3) . ? C2 H2' 1.04(3) . ? C3 C3A 1.496(3) . ? C3 H3 1.01(3) . ? C3 H3' 0.82(3) . ? C3A C11B 1.351(3) . ? C3A C4 1.504(3) . ? C4 N5 1.505(3) . ? C4 C12 1.529(3) . ? C4 H4 0.99(2) . ? N5 N6 1.246(2) . ? N6 C7 1.499(3) . ? C7 C7A 1.510(3) . ? C7 C12 1.525(3) . ? C7 H7 0.95(2) . ? C7A C8 1.394(3) . ? C7A C11A 1.412(3) . ? C8 C9 1.375(3) . ? C8 H8 0.93(2) . ? C9 C10 1.355(3) . ? C9 H9 1.00(3) . ? C10 C11 1.364(3) . ? C10 H10 1.00(3) . ? C11 C11A 1.412(3) . ? C11 H11 1.00(2) . ? C11A C11B 1.479(3) . ? C12 C121 1.511(3) . ? C12 H12 0.93(2) . ? C121 C126 1.386(3) . ? C121 C122 1.387(3) . ? C122 C123 1.384(3) . ? C122 H122 0.97(2) . ? C123 C124 1.376(3) . ? C123 H123 0.99(2) . ? C124 C125 1.385(3) . ? C124 H124 0.95(3) . ? C125 C126 1.380(3) . ? C125 H125 0.95(2) . ? C126 H126 0.95(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11B C1 C2 105.71(19) . . ? C11B C1 H1 112.1(15) . . ? C2 C1 H1 111.5(15) . . ? C11B C1 H1' 109.4(16) . . ? C2 C1 H1' 110.0(16) . . ? H1 C1 H1' 108(2) . . ? C3 C2 C1 106.8(2) . . ? C3 C2 H2 117(2) . . ? C1 C2 H2 118(2) . . ? C3 C2 H2' 106.2(16) . . ? C1 C2 H2' 106.1(16) . . ? H2 C2 H2' 101(2) . . ? C3A C3 C2 105.1(2) . . ? C3A C3 H3 108.9(15) . . ? C2 C3 H3 112.3(15) . . ? C3A C3 H3' 110(2) . . ? C2 C3 H3' 113(2) . . ? H3 C3 H3' 107(3) . . ? C11B C3A C3 112.91(19) . . ? C11B C3A C4 126.64(18) . . ? C3 C3A C4 120.30(19) . . ? C3A C4 N5 103.74(15) . . ? C3A C4 C12 114.90(17) . . ? N5 C4 C12 104.28(16) . . ? C3A C4 H4 110.1(13) . . ? N5 C4 H4 110.6(12) . . ? C12 C4 H4 112.7(12) . . ? N6 N5 C4 110.79(16) . . ? N5 N6 C7 111.18(16) . . ? N6 C7 C7A 107.22(15) . . ? N6 C7 C12 104.74(16) . . ? C7A C7 C12 115.72(16) . . ? N6 C7 H7 107.4(12) . . ? C7A C7 H7 109.6(12) . . ? C12 C7 H7 111.6(12) . . ? C8 C7A C11A 119.06(18) . . ? C8 C7A C7 117.25(18) . . ? C11A C7A C7 123.69(17) . . ? C9 C8 C7A 122.0(2) . . ? C9 C8 H8 119.3(14) . . ? C7A C8 H8 118.7(14) . . ? C10 C9 C8 119.5(2) . . ? C10 C9 H9 121.0(14) . . ? C8 C9 H9 119.4(14) . . ? C9 C10 C11 120.1(2) . . ? C9 C10 H10 120.3(14) . . ? C11 C10 H10 119.6(14) . . ? C10 C11 C11A 122.8(2) . . ? C10 C11 H11 120.1(13) . . ? C11A C11 H11 117.0(13) . . ? C7A C11A C11 116.41(19) . . ? C7A C11A C11B 126.09(17) . . ? C11 C11A C11B 117.50(18) . . ? C3A C11B C11A 130.16(18) . . ? C3A C11B C1 109.31(19) . . ? C11A C11B C1 120.52(18) . . ? C121 C12 C7 114.99(16) . . ? C121 C12 C4 113.06(16) . . ? C7 C12 C4 99.02(15) . . ? C121 C12 H12 109.9(12) . . ? C7 C12 H12 109.6(13) . . ? C4 C12 H12 109.9(13) . . ? C126 C121 C122 117.54(18) . . ? C126 C121 C12 122.74(17) . . ? C122 C121 C12 119.71(17) . . ? C123 C122 C121 121.46(19) . . ? C123 C122 H122 119.5(13) . . ? C121 C122 H122 119.0(13) . . ? C124 C123 C122 120.0(2) . . ? C124 C123 H123 120.9(14) . . ? C122 C123 H123 119.0(14) . . ? C123 C124 C125 119.5(2) . . ? C123 C124 H124 118.4(15) . . ? C125 C124 H124 122.1(15) . . ? C126 C125 C124 119.9(2) . . ? C126 C125 H125 121.2(14) . . ? C124 C125 H125 118.9(14) . . ? C125 C126 C121 121.57(19) . . ? C125 C126 H126 121.6(14) . . ? C121 C126 H126 116.8(14) . . ? 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 C11B C1 C2 C3 4.1(3) . . . . ? C1 C2 C3 C3A -3.3(3) . . . . ? C2 C3 C3A C11B 1.3(3) . . . . ? C2 C3 C3A C4 -174.6(2) . . . . ? C11B C3A C4 N5 -73.4(2) . . . . ? C3 C3A C4 N5 101.9(2) . . . . ? C11B C3A C4 C12 39.8(3) . . . . ? C3 C3A C4 C12 -144.9(2) . . . . ? C3A C4 N5 N6 99.65(19) . . . . ? C12 C4 N5 N6 -21.0(2) . . . . ? C4 N5 N6 C7 1.5(2) . . . . ? N5 N6 C7 C7A -104.83(18) . . . . ? N5 N6 C7 C12 18.6(2) . . . . ? N6 C7 C7A C8 -108.13(19) . . . . ? C12 C7 C7A C8 135.44(19) . . . . ? N6 C7 C7A C11A 71.7(2) . . . . ? C12 C7 C7A C11A -44.7(3) . . . . ? C11A C7A C8 C9 1.2(3) . . . . ? C7 C7A C8 C9 -178.90(19) . . . . ? C7A C8 C9 C10 0.4(3) . . . . ? C8 C9 C10 C11 -1.7(3) . . . . ? C9 C10 C11 C11A 1.3(3) . . . . ? C8 C7A C11A C11 -1.6(3) . . . . ? C7 C7A C11A C11 178.55(17) . . . . ? C8 C7A C11A C11B 177.62(18) . . . . ? C7 C7A C11A C11B -2.2(3) . . . . ? C10 C11 C11A C7A 0.4(3) . . . . ? C10 C11 C11A C11B -178.90(19) . . . . ? C3 C3A C11B C11A -177.3(2) . . . . ? C4 C3A C11B C11A -1.7(3) . . . . ? C3 C3A C11B C1 1.3(3) . . . . ? C4 C3A C11B C1 176.9(2) . . . . ? C7A C11A C11B C3A 4.8(3) . . . . ? C11 C11A C11B C3A -176.0(2) . . . . ? C7A C11A C11B C1 -173.62(19) . . . . ? C11 C11A C11B C1 5.6(3) . . . . ? C2 C1 C11B C3A -3.4(3) . . . . ? C2 C1 C11B C11A 175.4(2) . . . . ? N6 C7 C12 C121 91.95(19) . . . . ? C7A C7 C12 C121 -150.24(17) . . . . ? N6 C7 C12 C4 -28.83(18) . . . . ? C7A C7 C12 C4 88.99(19) . . . . ? C3A C4 C12 C121 154.49(17) . . . . ? N5 C4 C12 C121 -92.66(18) . . . . ? C3A C4 C12 C7 -83.34(19) . . . . ? N5 C4 C12 C7 29.51(18) . . . . ? C7 C12 C121 C126 -37.1(3) . . . . ? C4 C12 C121 C126 75.6(2) . . . . ? C7 C12 C121 C122 144.33(19) . . . . ? C4 C12 C121 C122 -102.9(2) . . . . ? C126 C121 C122 C123 0.1(3) . . . . ? C12 C121 C122 C123 178.7(2) . . . . ? C121 C122 C123 C124 -0.4(4) . . . . ? C122 C123 C124 C125 0.2(4) . . . . ? C123 C124 C125 C126 0.2(4) . . . . ? C124 C125 C126 C121 -0.5(4) . . . . ? C122 C121 C126 C125 0.4(3) . . . . ? C12 C121 C126 C125 -178.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 60.02 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.163 _refine_diff_density_min -0.170 _refine_diff_density_rms 0.036 data_pw0282 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C20 H18' _chemical_formula_weight 258.34 _chemical_melting_point ? _chemical_compound_source ? 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pccn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' 'x+1/2, -y, -z+1/2' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' '-x-1/2, y, z-1/2' 'x, -y-1/2, z-1/2' _cell_length_a 18.699(2) _cell_length_b 22.045(2) _cell_length_c 6.898(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2843.6(8) _cell_formula_units_Z 8 _cell_measurement_temperature 220(2) _cell_measurement_reflns_used 60 _cell_measurement_theta_min 20 _cell_measurement_theta_max 22 _exptl_crystal_description block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.207 _exptl_crystal_density_method ? _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 0.509 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 220(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ? _diffrn_measurement_method omega-theta _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2141 _diffrn_reflns_av_R_equivalents 0.0122 _diffrn_reflns_av_sigmaI/netI 0.0702 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 60.13 _reflns_number_total 2094 _reflns_number_observed 1209 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 4 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0631P)^2^+0.0000P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00058(14) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2090 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1163 _refine_ls_R_factor_obs 0.0563 _refine_ls_wR_factor_all 0.1468 _refine_ls_wR_factor_obs 0.1182 _refine_ls_goodness_of_fit_all 1.006 _refine_ls_goodness_of_fit_obs 1.111 _refine_ls_restrained_S_all 1.016 _refine_ls_restrained_S_obs 1.111 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group C1 C 0.9414(2) -0.17808(15) 0.2737(6) 0.0543(11) Uani 1 d . . H1A H 0.8998(2) -0.19654(15) 0.2106(6) 0.065 Uiso 1 calc R . H1B H 0.9610(2) -0.20671(15) 0.3686(6) 0.065 Uiso 1 calc R . C2 C 0.9980(2) -0.1600(2) 0.1247(7) 0.0634(12) Uani 1 d . . H2A H 0.9888(2) -0.1799(2) 0.0003(7) 0.076 Uiso 1 calc R . H2B H 1.0458(2) -0.1716(2) 0.1696(7) 0.076 Uiso 1 calc R . C3 C 0.9927(2) -0.09088(15) 0.1032(5) 0.0427(9) Uani 1 d . . H3A H 1.0402(2) -0.07214(15) 0.1048(5) 0.051 Uiso 1 calc R . H3B H 0.9683(2) -0.07983(15) -0.0175(5) 0.051 Uiso 1 calc R . C3A C 0.9500(2) -0.07201(14) 0.2756(5) 0.0312(8) Uani 1 d . . C3B C 0.9364(2) -0.00874(13) 0.3328(5) 0.0295(8) Uani 1 d . . H3B1 H 0.9761(2) 0.02029(13) 0.3129(5) 0.035 Uiso 1 calc R . C4 C 0.8609(2) 0.01682(13) 0.3161(5) 0.0297(8) Uani 1 d . . H4 H 0.8244(2) -0.01120(13) 0.2638(5) 0.036 Uiso 1 calc R . C4A C 0.8914(2) 0.00035(14) 0.5135(5) 0.0282(8) Uani 1 d . . H4A H 0.9054(2) 0.03519(14) 0.5957(5) 0.034 Uiso 1 calc R . C4B C 0.86664(15) -0.05428(14) 0.6203(5) 0.0298(8) Uani 1 d . . C5 C 0.8317(2) -0.0483(2) 0.7964(5) 0.0362(8) Uani 1 d . . H5 H 0.8255(2) -0.0094(2) 0.8501(5) 0.043 Uiso 1 calc R . C6 C 0.8059(2) -0.0983(2) 0.8945(5) 0.0451(10) Uani 1 d . . H6 H 0.7814(2) -0.0932(2) 1.0125(5) 0.054 Uiso 1 calc R . C7 C 0.8159(2) -0.1556(2) 0.8196(6) 0.0498(10) Uani 1 d . . H7 H 0.7980(2) -0.1897(2) 0.8855(6) 0.060 Uiso 1 calc R . C8 C 0.8522(2) -0.1625(2) 0.6475(6) 0.0464(10) Uani 1 d . . H8 H 0.8592(2) -0.2017(2) 0.5975(6) 0.056 Uiso 1 calc R . C8A C 0.8790(2) -0.11303(14) 0.5455(5) 0.0336(9) Uani 1 d . . C8B C 0.9217(2) -0.11892(14) 0.3688(5) 0.0352(8) Uani 1 d . . C41 C 0.8519(2) 0.08153(13) 0.2652(5) 0.0299(8) Uani 1 d . . C42 C 0.7980(2) 0.09860(14) 0.1370(5) 0.0369(9) Uani 1 d . . H42 H 0.7672(2) 0.06900(14) 0.0854(5) 0.044 Uiso 1 calc R . C43 C 0.7893(2) 0.15877(15) 0.0851(5) 0.0466(10) Uani 1 d . . H43 H 0.7524(2) 0.16965(15) -0.0006(5) 0.056 Uiso 1 calc R . C44 C 0.8339(2) 0.2027(2) 0.1567(6) 0.0496(10) Uani 1 d . . H44 H 0.8278(2) 0.2435(2) 0.1204(6) 0.060 Uiso 1 calc R . C45 C 0.8879(2) 0.1864(2) 0.2832(6) 0.0457(10) Uani 1 d . . H45 H 0.9184(2) 0.2163(2) 0.3343(6) 0.055 Uiso 1 calc R . C46 C 0.8973(2) 0.12647(14) 0.3347(5) 0.0369(9) Uani 1 d . . H46 H 0.9350(2) 0.11584(14) 0.4182(5) 0.044 Uiso 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 C1 0.065(3) 0.033(2) 0.065(3) -0.002(2) 0.009(2) 0.013(2) C2 0.083(3) 0.045(2) 0.062(3) -0.003(2) 0.023(3) 0.023(2) C3 0.040(2) 0.045(2) 0.042(2) -0.003(2) 0.004(2) 0.009(2) C3A 0.030(2) 0.034(2) 0.030(2) 0.001(2) 0.000(2) 0.0085(14) C3B 0.027(2) 0.029(2) 0.033(2) 0.000(2) 0.000(2) 0.0033(14) C4 0.026(2) 0.028(2) 0.035(2) -0.002(2) -0.005(2) 0.0012(14) C4A 0.028(2) 0.026(2) 0.031(2) -0.0039(14) 0.000(2) 0.0010(14) C4B 0.026(2) 0.029(2) 0.034(2) 0.001(2) -0.0040(15) 0.0029(14) C5 0.035(2) 0.042(2) 0.032(2) -0.001(2) 0.001(2) 0.002(2) C6 0.039(2) 0.058(2) 0.038(2) 0.004(2) 0.006(2) 0.002(2) C7 0.050(2) 0.051(2) 0.049(3) 0.019(2) 0.008(2) -0.001(2) C8 0.055(2) 0.031(2) 0.054(3) 0.010(2) -0.001(2) 0.004(2) C8A 0.033(2) 0.031(2) 0.036(2) 0.006(2) -0.002(2) 0.0036(15) C8B 0.037(2) 0.030(2) 0.038(2) -0.002(2) -0.002(2) 0.008(2) C41 0.030(2) 0.029(2) 0.031(2) 0.000(2) 0.001(2) 0.0053(15) C42 0.042(2) 0.037(2) 0.033(2) -0.001(2) -0.003(2) 0.007(2) C43 0.058(2) 0.043(2) 0.039(2) 0.002(2) -0.005(2) 0.020(2) C44 0.062(2) 0.033(2) 0.053(3) 0.014(2) 0.016(2) 0.016(2) C45 0.042(2) 0.033(2) 0.062(3) 0.000(2) 0.011(2) -0.003(2) C46 0.035(2) 0.028(2) 0.047(2) -0.001(2) 0.001(2) 0.0022(15) _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 C8B 1.506(4) . ? C1 C2 1.528(5) . ? C2 C3 1.534(4) . ? C3 C3A 1.491(4) . ? C3A C8B 1.328(4) . ? C3A C3B 1.472(4) . ? C3B C4A 1.517(4) . ? C3B C4 1.523(4) . ? C4 C41 1.479(4) . ? C4 C4A 1.520(4) . ? C4A C4B 1.486(4) . ? C4B C5 1.386(4) . ? C4B C8A 1.413(4) . ? C5 C6 1.381(4) . ? C6 C7 1.377(5) . ? C7 C8 1.377(5) . ? C8 C8A 1.390(5) . ? C8A C8B 1.463(5) . ? C41 C46 1.390(4) . ? C41 C42 1.393(4) . ? C42 C43 1.383(4) . ? C43 C44 1.370(5) . ? C44 C45 1.383(5) . ? C45 C46 1.379(4) . ? 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 C8B C1 C2 103.7(3) . . ? C1 C2 C3 106.2(3) . . ? C3A C3 C2 103.6(3) . . ? C8B C3A C3B 122.6(3) . . ? C8B C3A C3 112.5(3) . . ? C3B C3A C3 124.8(3) . . ? C3A C3B C4A 116.2(3) . . ? C3A C3B C4 119.4(3) . . ? C4A C3B C4 60.0(2) . . ? C41 C4 C4A 119.1(3) . . ? C41 C4 C3B 118.7(3) . . ? C4A C4 C3B 59.8(2) . . ? C4B C4A C3B 118.2(3) . . ? C4B C4A C4 121.4(3) . . ? C3B C4A C4 60.2(2) . . ? C5 C4B C8A 119.0(3) . . ? C5 C4B C4A 120.3(3) . . ? C8A C4B C4A 120.8(3) . . ? C6 C5 C4B 121.2(3) . . ? C7 C6 C5 120.0(3) . . ? C8 C7 C6 119.5(4) . . ? C7 C8 C8A 121.8(4) . . ? C8 C8A C4B 118.4(3) . . ? C8 C8A C8B 123.2(3) . . ? C4B C8A C8B 118.3(3) . . ? C3A C8B C8A 123.5(3) . . ? C3A C8B C1 111.4(3) . . ? C8A C8B C1 125.0(3) . . ? C46 C41 C42 117.9(3) . . ? C46 C41 C4 122.4(3) . . ? C42 C41 C4 119.6(3) . . ? C43 C42 C41 120.5(3) . . ? C44 C43 C42 120.9(3) . . ? C43 C44 C45 119.2(3) . . ? C46 C45 C44 120.3(3) . . ? C45 C46 C41 121.1(3) . . ? 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 C8B C1 C2 C3 -15.2(4) . . . . ? C1 C2 C3 C3A 15.4(4) . . . . ? C2 C3 C3A C8B -10.2(4) . . . . ? C2 C3 C3A C3B 173.3(3) . . . . ? C8B C3A C3B C4A 3.7(5) . . . . ? C3 C3A C3B C4A 179.9(3) . . . . ? C8B C3A C3B C4 -65.1(5) . . . . ? C3 C3A C3B C4 111.2(4) . . . . ? C3A C3B C4 C41 -146.1(3) . . . . ? C4A C3B C4 C41 108.8(3) . . . . ? C3A C3B C4 C4A 105.1(3) . . . . ? C4A C3B C4 C4A 0.0 . . . . ? C3A C3B C4A C4B 1.7(4) . . . . ? C4 C3B C4A C4B 112.0(3) . . . . ? C3A C3B C4A C4 -110.3(3) . . . . ? C4 C3B C4A C4 0.0 . . . . ? C41 C4 C4A C4B 145.0(3) . . . . ? C3B C4 C4A C4B -106.8(3) . . . . ? C41 C4 C4A C3B -108.2(3) . . . . ? C3B C4 C4A C3B 0.0 . . . . ? C3B C4A C4B C5 173.4(3) . . . . ? C4 C4A C4B C5 -116.0(3) . . . . ? C3B C4A C4B C8A -5.9(4) . . . . ? C4 C4A C4B C8A 64.7(4) . . . . ? C8A C4B C5 C6 -3.2(5) . . . . ? C4A C4B C5 C6 177.5(3) . . . . ? C4B C5 C6 C7 1.4(5) . . . . ? C5 C6 C7 C8 0.5(5) . . . . ? C6 C7 C8 C8A -0.5(6) . . . . ? C7 C8 C8A C4B -1.4(5) . . . . ? C7 C8 C8A C8B 176.0(3) . . . . ? C5 C4B C8A C8 3.2(5) . . . . ? C4A C4B C8A C8 -177.5(3) . . . . ? C5 C4B C8A C8B -174.4(3) . . . . ? C4A C4B C8A C8B 4.9(4) . . . . ? C3B C3A C8B C8A -5.0(5) . . . . ? C3 C3A C8B C8A 178.4(3) . . . . ? C3B C3A C8B C1 177.1(3) . . . . ? C3 C3A C8B C1 0.4(4) . . . . ? C8 C8A C8B C3A -176.9(3) . . . . ? C4B C8A C8B C3A 0.6(5) . . . . ? C8 C8A C8B C1 0.8(5) . . . . ? C4B C8A C8B C1 178.2(3) . . . . ? C2 C1 C8B C3A 9.5(4) . . . . ? C2 C1 C8B C8A -168.4(3) . . . . ? C4A C4 C41 C46 31.7(5) . . . . ? C3B C4 C41 C46 -37.7(5) . . . . ? C4A C4 C41 C42 -151.0(3) . . . . ? C3B C4 C41 C42 139.6(3) . . . . ? C46 C41 C42 C43 -1.5(5) . . . . ? C4 C41 C42 C43 -179.0(3) . . . . ? C41 C42 C43 C44 0.6(5) . . . . ? C42 C43 C44 C45 -0.2(6) . . . . ? C43 C44 C45 C46 0.7(6) . . . . ? C44 C45 C46 C41 -1.6(6) . . . . ? C42 C41 C46 C45 2.0(5) . . . . ? C4 C41 C46 C45 179.4(3) . . . . ? _refine_diff_density_max 0.170 _refine_diff_density_min -0.180 _refine_diff_density_rms 0.045 data_pw0375 _audit_creation_date 97-08-19 _audit_creation_method CRYSTALS # pw0375 in P21/c _computing_data_collection DIF4 _computing_cell_refinement DIF4 _computing_data_reduction REDU4 _computing_structure_refinement ; CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996) ; _computing_publication_material ; CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996) ; _computing_molecular_graphics ; CAMERON (Watkin, Prout & Pearce, 1996) ; # _computing_structure_solution 'SHELXS86 (Sheldrick, 1986)' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' #========================================================================== # NOW THE GOODIES TO BE ENTERED BY HAND #========================================================================== _chemical_melting_point ? _diffrn_radiation_monochromator graphite _diffrn_measurement_device ; Stoe Stadi-4 diffractometer equipped with an Oxford Cryosystems l.t. device. ; _refine_ls_matrix_type full _refine_ls_weighting_scheme ; Chebychev polynomial (Carruthers & Watkin, 1979) ; _atom_sites_solution_primary Direct_Methods _atom_sites_solution_hydrogens Geometric _refine_ls_hydrogen_treatment ; H atoms placed geometrically after each cycle ; #**************************************************************************** _chemical_name_systematic ; # IUPAC name, in full ? ; _cell_length_a 17.081(2) _cell_angle_alpha 90 _cell_length_b 7.0507(8) _cell_angle_beta 112.113(6) _cell_length_c 16.116(2) _cell_angle_gamma 90 _cell_volume 1798.11 _symmetry_cell_setting 'Monoclinic ' _symmetry_space_group_name_H-M 'P 1 21/c 1 ' loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' '-x,-y,-z' '-x,y+1/2,-z+1/2' 'x,-y+1/2,z+1/2' loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0170 0.0090 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International_Tables_Vol_IV_Table_2.2B' 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997 0.0030 'International_Tables_Vol_IV_Table_2.2B' 'N ' 0.0290 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International_Tables_Vol_IV_Table_2.2B' _chemical_formula_sum ' C24 H20 N2 ' _chemical_formula_moiety ' C24 H20 N2 ' _chemical_compound_source ; ? ; _chemical_formula_weight 336.44 _cell_measurement_reflns_used 46 _cell_measurement_theta_min 20 _cell_measurement_theta_max 22 _cell_measurement_temperature 220 _cell_formula_units_Z 4.00 _exptl_crystal_description ' block ' _exptl_crystal_colour ' yellow ' _exptl_crystal_size_min 0.19 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_max 0.47 _exptl_crystal_density_diffrn 1.24 _exptl_crystal_density_meas ? _exptl_crystal_F_000 713.74 _exptl_absorpt_coefficient_mu 0.53 _exptl_absorpt_correction_type ? _diffrn_standards_interval_time 60 _diffrn_standards_interval_count ? _diffrn_standards_number 3 _diffrn_standards_decay_% 5.00 _diffrn_ambient_temperature 220 _diffrn_reflns_number 4128 _reflns_number_total 3184 _diffrn_reflns_av_R_equivalents 0.02 _reflns_number_observed 2633 _diffrn_reflns_theta_min 2.79 _diffrn_reflns_theta_max 70.08 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 15 _reflns_limit_h_min -20 _reflns_limit_h_max 19 _reflns_limit_k_min 0 _reflns_limit_k_max 8 _reflns_limit_l_min 0 _reflns_limit_l_max 18 _reflns_observed_criterion >2.00\s(I) _refine_diff_density_min -0.18 _refine_diff_density_max 0.20 _refine_ls_number_reflns 2633 _refine_ls_number_parameters 236 _refine_ls_R_factor_obs 0.0451 _refine_ls_wR_factor_obs 0.0475 _refine_ls_goodness_of_fit_obs 1.1246 _refine_ls_shift/esd_max 0.001145 _refine_ls_structure_factor_coef F _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54180 _diffrn_measurement_method 'Omega-theta with learnt-profile (Clegg)' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_thermal_displace_type N1 0.68007(9) 0.2600(2) 0.09828(9) 0.0369 1.0000 Uani N2 0.69633(9) 0.4171(2) 0.05925(9) 0.0390 1.0000 Uani C3 0.7405(1) 0.3938(2) 0.0100(1) 0.0400 1.0000 Uani C31 0.7832(1) 0.2210(2) 0.0038(1) 0.0329 1.0000 Uani C4 0.8389(1) 0.2167(2) -0.0417(1) 0.0375 1.0000 Uani C5 0.8822(1) 0.0527(3) -0.0433(1) 0.0427 1.0000 Uani C6 0.8717(1) -0.1074(3) 0.0008(1) 0.0455 1.0000 Uani C7 0.8178(1) -0.1037(2) 0.0474(1) 0.0399 1.0000 Uani C71 0.7731(1) 0.0592(2) 0.0486(1) 0.0321 1.0000 Uani C8 0.7085(1) 0.0612(2) 0.0922(1) 0.0328 1.0000 Uani C81 0.6298(1) -0.0515(3) 0.0346(1) 0.0431 1.0000 Uani C9 0.7384(1) -0.0106(2) 0.1915(1) 0.0345 1.0000 Uani C91 0.8330(1) -0.0087(2) 0.2463(1) 0.0340 1.0000 Uani C92 0.8800(1) 0.1561(2) 0.2576(1) 0.0407 1.0000 Uani C93 0.9653(1) 0.1588(3) 0.3100(1) 0.0473 1.0000 Uani C94 1.0048(1) -0.0041(3) 0.3531(1) 0.0509 1.0000 Uani C95 0.9589(1) -0.1685(3) 0.3433(1) 0.0535 1.0000 Uani C96 0.8731(1) -0.1716(3) 0.2897(1) 0.0451 1.0000 Uani C10 0.6934(1) 0.1265(2) 0.2302(1) 0.0376 1.0000 Uani C11 0.6657(1) 0.2782(2) 0.1785(1) 0.0345 1.0000 Uani C111 0.6218(1) 0.4474(2) 0.1939(1) 0.0339 1.0000 Uani C112 0.6519(1) 0.5409(2) 0.2755(1) 0.0397 1.0000 Uani C113 0.6078(1) 0.6949(3) 0.2896(1) 0.0458 1.0000 Uani C114 0.5339(1) 0.7552(3) 0.2227(1) 0.0493 1.0000 Uani C115 0.5036(1) 0.6611(3) 0.1422(1) 0.0512 1.0000 Uani C116 0.5471(1) 0.5075(3) 0.1271(1) 0.0443 1.0000 Uani H31 0.7460 0.5046 -0.0263 0.0408 1.0000 Uiso H41 0.8475 0.3327 -0.0729 0.0375 1.0000 Uiso H51 0.9214 0.0500 -0.0764 0.0419 1.0000 Uiso H61 0.9036 -0.2260 -0.0007 0.0461 1.0000 Uiso H71 0.8101 -0.2197 0.0796 0.0405 1.0000 Uiso H811 0.6457 -0.1855 0.0289 0.0421 1.0000 Uiso H812 0.6043 0.0077 -0.0261 0.0421 1.0000 Uiso H813 0.5873 -0.0489 0.0640 0.0421 1.0000 Uiso H91 0.7260 -0.1481 0.1957 0.0354 1.0000 Uiso H921 0.8511 0.2755 0.2278 0.0403 1.0000 Uiso H931 0.9987 0.2783 0.3164 0.0467 1.0000 Uiso H941 1.0666 -0.0026 0.3913 0.0482 1.0000 Uiso H951 0.9875 -0.2868 0.3741 0.0518 1.0000 Uiso H961 0.8400 -0.2922 0.2824 0.0450 1.0000 Uiso H101 0.6848 0.1052 0.2876 0.0391 1.0000 Uiso H1121 0.7054 0.4969 0.3242 0.0398 1.0000 Uiso H1131 0.6298 0.7630 0.3482 0.0473 1.0000 Uiso H1141 0.5022 0.8666 0.2333 0.0520 1.0000 Uiso H1151 0.4494 0.7031 0.0941 0.0515 1.0000 Uiso H1161 0.5251 0.4398 0.0684 0.0439 1.0000 Uiso 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 0.0484(8) 0.0285(7) 0.0411(8) 0.0056(6) 0.0250(7) 0.0058(6) N2 0.0517(8) 0.0307(7) 0.0396(8) 0.0065(6) 0.0230(7) 0.0063(6) C3 0.053(1) 0.0323(8) 0.0411(9) 0.0066(7) 0.0255(8) 0.0013(8) C31 0.0347(8) 0.0349(8) 0.0287(8) -0.0011(7) 0.0117(6) -0.0031(7) C4 0.0379(8) 0.0428(9) 0.0332(9) -0.0003(7) 0.0150(7) -0.0050(7) C5 0.0371(8) 0.057(1) 0.0365(9) -0.0016(8) 0.0173(7) 0.0030(8) C6 0.047(1) 0.048(1) 0.045(1) 0.0000(8) 0.0216(8) 0.0128(8) C7 0.050(1) 0.0340(9) 0.0391(9) 0.0036(7) 0.0212(8) 0.0061(8) C71 0.0344(8) 0.0320(8) 0.0294(8) -0.0021(7) 0.0113(6) -0.0001(6) C8 0.0351(8) 0.0280(8) 0.0375(9) 0.0037(7) 0.0162(7) 0.0028(6) C81 0.0398(9) 0.040(1) 0.048(1) 0.0012(8) 0.0148(8) -0.0019(8) C9 0.0391(8) 0.0287(8) 0.0405(9) 0.0081(7) 0.0205(7) 0.0028(7) C91 0.0400(8) 0.0363(9) 0.0308(8) 0.0041(7) 0.0191(7) 0.0062(7) C92 0.0450(9) 0.0372(9) 0.0404(9) 0.0038(7) 0.0167(8) 0.0042(8) C93 0.045(1) 0.053(1) 0.045(1) -0.0047(9) 0.0180(8) -0.0040(9) C94 0.0389(9) 0.065(1) 0.046(1) 0.0001(9) 0.0129(8) 0.0055(9) C95 0.048(1) 0.056(1) 0.053(1) 0.013(1) 0.0150(9) 0.0159(9) C96 0.047(1) 0.0405(9) 0.051(1) 0.0105(8) 0.0219(8) 0.0061(8) C10 0.0382(8) 0.0409(9) 0.0403(9) 0.0081(7) 0.0222(7) 0.0060(7) C11 0.0353(8) 0.0361(9) 0.0359(9) 0.0032(7) 0.0178(7) 0.0030(7) C111 0.0353(8) 0.0352(8) 0.0369(9) 0.0071(7) 0.0200(7) 0.0049(7) C112 0.0380(8) 0.0393(9) 0.045(1) 0.0005(8) 0.0187(8) -0.0015(7) C113 0.055(1) 0.0371(9) 0.053(1) -0.0062(8) 0.0297(9) -0.0048(8) C114 0.056(1) 0.037(1) 0.070(1) 0.0062(9) 0.040(1) 0.0118(8) C115 0.049(1) 0.052(1) 0.055(1) 0.0147(9) 0.0223(9) 0.0179(9) C116 0.048(1) 0.049(1) 0.0377(9) 0.0059(8) 0.0174(8) 0.0090(8) _refine_ls_extinction_coef 31.5(33) _refine_ls_extinction_method 'Larson 1970 Crystallographic Computing eq 22' loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 . N2 . 1.353(2) yes N1 . C8 . 1.499(2) yes N1 . C11 . 1.411(2) yes N2 . C3 . 1.294(2) yes C3 . C31 . 1.443(2) yes C3 . H31 . 1.002(2) no C31 . C4 . 1.402(2) yes C31 . C71 . 1.395(2) yes C4 . C5 . 1.378(2) yes C4 . H41 . 1.000(2) no C5 . C6 . 1.381(3) yes C5 . H51 . 1.002(2) no C6 . C7 . 1.390(2) yes C6 . H61 . 1.003(2) no C7 . C71 . 1.384(2) yes C7 . H71 . 1.004(2) no C71 . C8 . 1.515(2) yes C8 . C81 . 1.537(2) yes C8 . C9 . 1.570(2) yes C81 . H811 . 0.997(2) no C81 . H812 . 1.000(2) no C81 . H813 . 1.005(2) no C9 . C91 . 1.522(2) yes C9 . C10 . 1.508(2) yes C9 . H91 . 1.000(2) no C91 . C92 . 1.385(2) yes C91 . C96 . 1.385(2) yes C92 . C93 . 1.382(3) yes C92 . H921 . 1.002(2) no C93 . C94 . 1.380(3) yes C93 . H931 . 1.001(2) no C94 . C95 . 1.375(3) yes C94 . H941 . 1.003(2) no C95 . C96 . 1.393(3) yes C95 . H951 . 0.999(2) no C96 . H961 . 1.003(2) no C10 . C11 . 1.328(2) yes C10 . H101 . 1.002(2) no C11 . C111 . 1.478(2) yes C111 . C112 . 1.386(2) yes C111 . C116 . 1.389(2) yes C112 . C113 . 1.388(2) yes C112 . H1121 . 1.003(2) no C113 . C114 . 1.382(3) yes C113 . H1131 . 0.998(2) no C114 . C115 . 1.373(3) yes C114 . H1141 . 1.004(2) no C115 . C116 . 1.386(3) yes C115 . H1151 . 1.003(2) no C116 . H1161 . 0.998(2) no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag N2 . N1 . C8 . 127.4(1) yes N2 . N1 . C11 . 119.3(1) yes C8 . N1 . C11 . 108.5(1) yes N1 . N2 . C3 . 116.8(1) yes N2 . C3 . C31 . 125.2(1) yes N2 . C3 . H31 . 117.7(2) no C31 . C3 . H31 . 117.1(2) no C3 . C31 . C4 . 121.0(1) yes C3 . C31 . C71 . 119.3(1) yes C4 . C31 . C71 . 119.6(1) yes C31 . C4 . C5 . 120.1(2) yes C31 . C4 . H41 . 120.2(2) no C5 . C4 . H41 . 119.7(2) no C4 . C5 . C6 . 120.2(2) yes C4 . C5 . H51 . 119.8(2) no C6 . C5 . H51 . 120.0(2) no C5 . C6 . C7 . 120.1(2) yes C5 . C6 . H61 . 119.6(2) no C7 . C6 . H61 . 120.3(2) no C6 . C7 . C71 . 120.3(2) yes C6 . C7 . H71 . 120.4(2) no C71 . C7 . H71 . 119.2(2) no C31 . C71 . C7 . 119.6(1) yes C31 . C71 . C8 . 119.1(1) yes C7 . C71 . C8 . 121.1(1) yes N1 . C8 . C71 . 110.5(1) yes N1 . C8 . C81 . 107.0(1) yes C71 . C8 . C81 . 109.8(1) yes N1 . C8 . C9 . 103.0(1) yes C71 . C8 . C9 . 117.1(1) yes C81 . C8 . C9 . 108.9(1) yes C8 . C81 . H811 . 109.8(1) no C8 . C81 . H812 . 109.6(2) no H811 . C81 . H812 . 109.7(2) no C8 . C81 . H813 . 109.2(2) no H811 . C81 . H813 . 109.3(2) no H812 . C81 . H813 . 109.1(2) no C8 . C9 . C91 . 117.1(1) yes C8 . C9 . C10 . 101.2(1) yes C91 . C9 . C10 . 110.4(1) yes C8 . C9 . H91 . 112.7(1) no C91 . C9 . H91 . 100.1(1) no C10 . C9 . H91 . 116.1(1) no C9 . C91 . C92 . 121.4(1) yes C9 . C91 . C96 . 120.1(1) yes C92 . C91 . C96 . 118.5(2) yes C91 . C92 . C93 . 121.2(2) yes C91 . C92 . H921 . 119.0(2) no C93 . C92 . H921 . 119.8(2) no C92 . C93 . C94 . 119.9(2) yes C92 . C93 . H931 . 120.2(2) no C94 . C93 . H931 . 119.9(2) no C93 . C94 . C95 . 119.7(2) yes C93 . C94 . H941 . 120.1(2) no C95 . C94 . H941 . 120.2(2) no C94 . C95 . C96 . 120.4(2) yes C94 . C95 . H951 . 119.7(2) no C96 . C95 . H951 . 119.9(2) no C91 . C96 . C95 . 120.3(2) yes C91 . C96 . H961 . 119.6(2) no C95 . C96 . H961 . 120.1(2) no C9 . C10 . C11 . 112.0(1) yes C9 . C10 . H101 . 124.1(2) no C11 . C10 . H101 . 123.9(2) no N1 . C11 . C10 . 110.9(1) yes N1 . C11 . C111 . 120.1(1) yes C10 . C11 . C111 . 129.0(1) yes C11 . C111 . C112 . 120.8(1) yes C11 . C111 . C116 . 119.5(2) yes C112 . C111 . C116 . 119.6(2) yes C111 . C112 . C113 . 119.8(2) yes C111 . C112 . H1121 . 119.9(2) no C113 . C112 . H1121 . 120.3(2) no C112 . C113 . C114 . 120.3(2) yes C112 . C113 . H1131 . 119.7(2) no C114 . C113 . H1131 . 119.9(2) no C113 . C114 . C115 . 119.8(2) yes C113 . C114 . H1141 . 120.1(2) no C115 . C114 . H1141 . 120.1(2) no C114 . C115 . C116 . 120.5(2) yes C114 . C115 . H1151 . 119.9(2) no C116 . C115 . H1151 . 119.6(2) no C111 . C116 . C115 . 119.9(2) yes C111 . C116 . H1161 . 119.8(2) no C115 . C116 . H1161 . 120.3(2) no