# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 1999 # CCDC Number: 207/374 # 8,8'-Dialkyl-1,1'-biisoquinoline: preparation, absolute configuration and # unexpected enantiomerization behaviour data_1 #8,8'-dimethyl-1,1'-biisoquinoline #------------------------------------------------------------------------------ _audit_creation_date 'Oct 11 11996' _audit_creation_method ? _audit_update_record ? #------------------------------------------------------------------------------ _computing_data_collection 'CAD4 express' _computing_cell_refinement 'CAD4 express' _computing_data_reduction 'UNICS III' _computing_structure_solution MULTAN78 _computing_structure_refinement 'The Block diagonal least squer' _computing_publication_material 'UNICS III' _computing_molecular_graphics ? #------------------------------------------------------------------------------ _chemical_compound_source ? _chemical_name_common ? _chemical_formula_weight 284.35 _chemical_formula_analytical ? _chemical_formula_sum 'C20 H16 N2 ' _chemical_formula_moiety 'C20 H16 N2 ' _chemical_formula_structural ? _chemical_melting_point ? #------------------------------------------------------------------------------ _cell_length_a 31.695(2) _cell_length_b 31.695(2) _cell_length_c 7.7985(7) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 120 _cell_volume 6784.7(8) _cell_formula_units_Z 18 _cell_measurement_temperature 296.7 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.55 _cell_measurement_theta_max 18.34 #------------------------------------------------------------------------------ _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M 'R_-3 ' _symmetry_Int_Tables_number 148 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -y,x-y,z -x+y,-x,z -x,-y,-z y,-x+y,-z x-y,x,-z 2/3+x,1/3+y,1/3+z 2/3-y,1/3+x-y,1/3+z 2/3-x+y,1/3-x,1/3+z 2/3-x,1/3-y,1/3-z 2/3+y,1/3-x+y,1/3-z 2/3+x-y,1/3+x,1/3-z 1/3+x,2/3+y,2/3+z 1/3-y,2/3+x-y,2/3+z 1/3-x+y,2/3-x,2/3+z 1/3-x,2/3-y,2/3-z 1/3+y,2/3-x+y,2/3-z 1/3+x-y,2/3+x,2/3-z #------------------------------------------------------------------------------ _exptl_crystal_description 'prism' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.540 _exptl_crystal_size_mid 0.500 _exptl_crystal_size_min 0.430 _exptl_crystal_density_diffrn 1.253 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2700 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details Tompa_analytical _exptl_absorpt_correction_T_min 0.986 _exptl_absorpt_correction_T_max 1.000 _exptl_special_details ; ? ; #------------------------------------------------------------------------------ _diffrn_special_details ; ? ; _diffrn_ambient_temperature 293 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'CAD4 sealed tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device_type 'Enraf nonius CAD4' _diffrn_measurement_method \w _diffrn_standards_number 3 _diffrn_standards_interval_count 120 _diffrn_standards_decay_% -2.40 #loop_ #_diffrn_standard_refln_index_h #_diffrn_standard_refln_index_k #_diffrn_standard_refln_index_l # 3 11 -2 11 -7 -3 4 7 3 _diffrn_reflns_number 3053 _reflns_number_total 2355 _reflns_number_gt 2215 _reflns_observed_criterion >2.0sigma(I) #_diffrn_reflns_av_R_equivalents 0.037 #_diffrn_reflns_av_sigmaI/netI 0.101 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 38 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2 _diffrn_reflns_theta_max 25.75 _diffrn_reflns_reduction_process 'Lp corrections applied' #------------------------------------------------------------------------------ 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_calc_flag N(2) N 0.2133(1) 0.2273(1) 0.2675(2) 0.042(1) Uani 1.00 d N(12) N 0.2678(1) 0.1685(1) 0.2369(3) 0.046(1) Uani 1.00 d C(1) C 0.2235(1) 0.2049(1) 0.1454(3) 0.033(1) Uani 1.00 d C(3) C 0.2185(1) 0.2719(1) 0.2315(3) 0.048(1) Uani 1.00 d C(4) C 0.2357(1) 0.2951(1) 0.0798(3) 0.043(1) Uani 1.00 d C(5) C 0.2667(1) 0.2961(1) -0.2107(3) 0.045(1) Uani 1.00 d C(6) C 0.2759(1) 0.2729(1) -0.3380(3) 0.050(1) Uani 1.00 d C(7) C 0.2646(1) 0.2243(1) -0.3159(3) 0.048(1) Uani 1.00 d C(8) C 0.2467(1) 0.1994(1) -0.1641(3) 0.038(1) Uani 1.00 d C(9) C 0.2391(1) 0.2241(1) -0.0236(3) 0.031(1) Uani 1.00 d C(10) C 0.2473(1) 0.2720(1) -0.0516(3) 0.036(1) Uani 1.00 d C(11) C 0.2230(1) 0.1599(1) 0.2102(3) 0.033(1) Uani 1.00 d C(13) C 0.2739(1) 0.1326(1) 0.3098(4) 0.053(1) Uani 1.00 d C(14) C 0.2359(1) 0.0891(1) 0.3591(3) 0.048(1) Uani 1.00 d C(15) C 0.1479(1) 0.0325(1) 0.3748(3) 0.052(1) Uani 1.00 d C(16) C 0.1020(1) 0.0221(1) 0.3371(4) 0.059(1) Uani 1.00 d C(17) C 0.0938(1) 0.0567(1) 0.2546(3) 0.051(1) Uani 1.00 d C(18) C 0.1311(1) 0.1026(1) 0.2102(3) 0.037(1) Uani 1.00 d C(19) C 0.1801(1) 0.1147(1) 0.2495(2) 0.032(1) Uani 1.00 d C(20) C 0.1880(1) 0.0787(1) 0.3294(3) 0.038(1) Uani 1.00 d C(21) C 0.2337(1) 0.1466(1) -0.1576(3) 0.058(1) Uani 1.00 d C(22) C 0.1181(1) 0.1369(1) 0.1239(3) 0.052(1) Uani 1.00 d H(3) H 0.215(1) 0.291(1) 0.334(4) 0.080(8) Uiso 1.00 calc H(4) H 0.242(1) 0.330(1) 0.056(3) 0.073(7) Uiso 1.00 calc H(5) H 0.270(1) 0.331(1) -0.223(3) 0.073(7) Uiso 1.00 calc H(6) H 0.291(1) 0.290(1) -0.457(3) 0.079(8) Uiso 1.00 calc H(7) H 0.270(1) 0.207(1) -0.420(3) 0.076(7) Uiso 1.00 calc H(13) H 0.309(1) 0.137(1) 0.307(4) 0.087(8) Uiso 1.00 calc H(14) H 0.242(1) 0.059(1) 0.403(3) 0.080(8) Uiso 1.00 calc H(15) H 0.156(1) 0.005(1) 0.436(3) 0.083(8) Uiso 1.00 calc H(16) H 0.071(1) -0.013(1) 0.377(4) 0.085(8) Uiso 1.00 calc H(17) H 0.057(1) 0.051(1) 0.218(4) 0.083(8) Uiso 1.00 calc H(21)1 H 0.256(1) 0.142(1) -0.088(3) 0.082(8) Uiso 1.00 calc H(21)2 H 0.200(1) 0.126(1) -0.111(3) 0.083(8) Uiso 1.00 calc H(21)3 H 0.234(1) 0.133(1) -0.271(3) 0.083(8) Uiso 1.00 calc H(22)1 H 0.135(1) 0.150(1) 0.002(3) 0.076(7) Uiso 1.00 calc H(22)2 H 0.081(1) 0.120(1) 0.092(3) 0.078(7) Uiso 1.00 calc H(22)3 H 0.125(1) 0.165(1) 0.205(3) 0.080(8) Uiso 1.00 calc loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 N(2) 0.070(1) 0.045(1) 0.047(1) 0.031(1) 0.001(1) -0.003(1) N(12) 0.049(1) 0.051(1) 0.074(1) 0.025(1) -0.007(1) 0.002(1) C(1) 0.040(1) 0.034(1) 0.047(1) 0.016(1) -0.004(1) 0.000(1) C(3) 0.081(2) 0.046(1) 0.061(2) 0.036(1) -0.004(1) -0.009(1) C(4) 0.063(1) 0.038(1) 0.065(1) 0.025(1) -0.010(1) -0.003(1) C(5) 0.047(1) 0.048(1) 0.068(2) 0.017(1) -0.002(1) 0.016(1) C(6) 0.053(1) 0.070(2) 0.060(1) 0.025(1) 0.011(1) 0.021(1) C(7) 0.055(1) 0.067(2) 0.055(1) 0.027(1) 0.011(1) 0.006(1) C(8) 0.046(1) 0.047(1) 0.050(1) 0.021(1) 0.004(1) 0.001(1) C(9) 0.034(1) 0.034(1) 0.046(1) 0.013(1) -0.002(1) 0.000(1) C(10) 0.038(1) 0.037(1) 0.054(1) 0.014(1) -0.007(1) 0.003(1) C(11) 0.046(1) 0.039(1) 0.041(1) 0.022(1) -0.002(1) -0.001(1) C(13) 0.062(2) 0.070(2) 0.084(2) 0.044(1) -0.012(1) -0.001(1) C(14) 0.081(2) 0.060(1) 0.058(1) 0.048(1) -0.006(1) 0.003(1) C(15) 0.093(2) 0.044(1) 0.055(1) 0.031(1) 0.016(1) 0.011(1) C(16) 0.080(2) 0.049(1) 0.072(2) 0.015(1) 0.023(1) 0.007(1) C(17) 0.054(1) 0.057(1) 0.069(2) 0.017(1) 0.010(1) -0.005(1) C(18) 0.047(1) 0.047(1) 0.045(1) 0.021(1) 0.001(1) -0.005(1) C(19) 0.050(1) 0.037(1) 0.034(1) 0.022(1) 0.002(1) -0.001(1) C(20) 0.067(1) 0.043(1) 0.039(1) 0.030(1) 0.003(1) 0.001(1) C(21) 0.104(2) 0.054(2) 0.064(2) 0.041(2) 0.017(2) -0.006(1) C(22) 0.054(1) 0.069(2) 0.080(2) 0.034(1) -0.016(1) 0.000(1) #------------------------------------------------------------------------------ _refine_special_details ; Refinement based on F against all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F, conventional R-factors (R) are calculated on F, with F set to zero for negative F. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. thus the refinement was done using all reflections. ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type block _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00078|Fo|^2^]' _refine_ls_hydrogen_treatment refall #_refine_ls_extinction_method # 'Zachariasen(1967) type 2 Gaussian isotropic' #_refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 2215 _refine_ls_number_parameters 264 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.0440 _refine_ls_R_factor_gt 0.0440 _refine_ls_wR_factor_ref 0.0410 _refine_ls_wR_factor_gt 0.0410 _refine_ls_goodness_of_fit_all 2.10 _refine_ls_shift/su_max 1.36 _refine_diff_density_min -0.17 _refine_diff_density_max 0.17 #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N(2) C(1) 1.320(3) N(2) C(3) 1.368(4) N(12) C(11) 1.322(3) N(12) C(13) 1.370(42 C(1) C(9) 1.432(3) C(1) C(11) 1.504(35 C(3) C(4) 1.355(3) C(3) H(3) 1.045(32) C(4) C(10) 1.411(4) C(4) H(4) 1.058(32) C(5) C(6) 1.351(4) C(5) C(10) 1.426(3) C(5) H(5) 1.049(33) C(6) C(7) 1.407(4) C(6) H(6) 1.056(26) C(7) C(8) 1.377(3) C(7) H(7) 1.036(31) C(8) C(9) 1.435(3) C(8) C(21) 1.510(4) C(9) C(10) 1.424(3) C(11) C(19) 1.432(2) C(13) C(14) 1.357(3) C(13) H(13) 1.047(35) C(14) C(20) 1.405(4) C(14) H(14) 1.094(36) C(15) C(16) 1.354(5) C(15) C(20) 1.423(3) C(15) H(15) 1.135(37) C(16) C(17) 1.404(5) C(16) H(16) 1.090(24) C(17) C(18) 1.383(3) C(17) H(17) 1.107(34) C(18) C(19) 1.432(3) C(18) C(22) 1.504(4) C(19) C(20) 1.427(4) C(21) H(21)1 0.960(34) C(21) H(21)2 1.001(26) C(21) H(21)3 0.980(29) C(22) H(22)1 1.063(26) C(22) H(22)2 1.041(28) C(22) H(22)3 1.019(30) #------------------------------------------------------------------------------ loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C(1) N(2) C(3) 118.2(2) C(11) N(12) C(13) 118.7(2) N(2) C(1) C(9) 124.1(2) N(2) C(1) C(11) 112.1(2) C(9) C(1) C(11) 123.3(2) N(2) C(3) C(4) 123.2(3) N(2) C(3) H(3) 116.6(17) C(4) C(3) H(3) 119.2(16) C(3) C(4) C(10) 119.4(3) C(3) C(4) H(4) 122.7(15) C(10) C(4) H(4) 117.8(15) C(6) C(5) C(10) 120.0(2) C(6) C(5) H(5) 124.0(15) C(10) C(5) H(5) 115.8(15) C(5) C(6) C(7) 120.1(2) C(5) C(6) H(6) 122.3(19) C(7) C(6) H(6) 117.7(19) C(6) C(7) C(8) 122.6(2) C(6) C(7) H(7) 117.5(16) C(8) C(7) H(7) 120.0(16) C(7) C(8) C(9) 118.6(2) C(7) C(8) C(21) 118.0(2) C(9) C(8) C(21) 123.4(2) C(1) C(9) C(8) 126.1(2) C(1) C(9) C(10) 115.7(2) C(8) C(9) C(10) 118.2(2) C(4) C(10) C(5) 120.6(2) C(4) C(10) C(9) 119.1(2) C(5) C(10) C(9) 120.3(2) N(12) C(11) C(1) 110.9(2) N(12) C(11) C(19) 123.8(2) C(1) C(11) C(19) 125.2(2) N(12) C(13) C(14) 122.6(3) N(12) C(13) H(13) 117.0(17) C(14) C(13) H(13) 119.6(17) C(13) C(14) C(20) 119.8(3) C(13) C(14) H(14) 121.1(14) C(20) C(14) H(14) 118.3(13) C(16) C(15) C(20) 119.5(3) C(16) C(15) H(15) 122.6(13) C(20) C(15) H(15) 117.8(13) C(15) C(16) C(17) 120.5(2) C(15) C(16) H(16) 119.6(20) C(17) C(16) H(16) 119.8(20) C(16) C(17) C(18) 122.6(3) C(16) C(17) H(17) 124.4(15) C(18) C(17) H(17) 113.0(15) C(17) C(18) C(19) 118.1(3) C(17) C(18) C(22) 118.1(2) C(19) C(18) C(22) 123.7(2) C(11) C(19) C(18) 125.6(2) C(11) C(19) C(20) 115.8(2) C(18) C(19) C(20) 118.6(2) C(14) C(20) C(15) 120.3(3) C(14) C(20) C(19) 119.2(2) C(15) C(20) C(19) 120.5(3) C(8) C(21) H(21)1 111.7(16) C(8) C(21) H(21)2 110.5(21) C(8) C(21) H(21)3 112.5(18) H(21)1 C(21) H(21)2 109.3(24) H(21)1 C(21) H(21)3 107.0(30) H(21)2 C(21) H(21)3 105.6(21) C(18) C(22) H(22)1 114.8(21) C(18) C(22) H(22)2 111.8(18) C(18) C(22) H(22)3 109.4(19) H(22)1 C(22) H(22)2 101.6(21) H(22)1 C(22) H(22)3 111.1(21) H(22)2 C(22) H(22)3 107.7(26) #------------------------------------------------------------------------------ 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 C(3) N(2) C(1) C(9) -0.9(3) C(3) N(2) C(1) C(11) 171.9(2) C(1) N(2) C(3) C(4) -3.1(4) C(13) N(12) C(11) C(1) 174.6(2) C(13) N(12) C(11) C(19) -1.5(4) C(11) N(12) C(13) C(14) -1.5(4) N(2) C(1) C(9) C(8) -174.5(2) N(2) C(1) C(9) C(10) 5.0(3) C(11) C(1) C(9) C(8) 13.4(3) C(11) C(1) C(9) C(10) -167.0(2) N(2) C(1) C(11) N(12) -101.2(2) N(2) C(1) C(11) C(19) 74.8(3) C(9) C(1) C(11) N(12) 71.7(3) C(9) C(1) C(11) C(19) -112.3(3) N(2) C(3) C(4) C(10) 2.5(4) C(3) C(4) C(10) C(5) -178.2(2) C(3) C(4) C(10) C(9) 2.0(4) C(10) C(5) C(6) C(7) 2.2(4) C(6) C(5) C(10) C(4) -177.4(2) C(6) C(5) C(10) C(9) 2.5(4) C(5) C(6) C(7) C(8) -3.6(4) C(6) C(7) C(8) C(9) 0.2(4) C(6) C(7) C(8) C(21) 177.2(3) C(7) C(8) C(9) C(1) -176.2(2) C(7) C(8) C(9) C(10) 4.3(3) C(21) C(8) C(9) C(1) 7.0(4) C(21) C(8) C(9) C(10) -172.5(2) C(1) C(9) C(10) C(4) -5.4(3) C(1) C(9) C(10) C(5) 174.8(2) C(8) C(9) C(10) C(4) 174.2(2) C(8) C(9) C(10) C(5) -5.7(3) N(12) C(11) C(19) C(18) -174.7(2) N(12) C(11) C(19) C(20) 3.0(3) C(1) C(11) C(19) C(18) 9.8(4) C(1) C(11) C(19) C(20) -172.5(2) N(12) C(13) C(14) C(20) 2.6(4) C(13) C(14) C(20) C(15) 177.7(3) C(13) C(14) C(20) C(19) -0.9(4) C(20) C(15) C(16) C(17) -0.3(4) C(16) C(15) C(20) C(14) -176.6(3) C(16) C(15) C(20) C(19) 2.0(4) C(15) C(16) C(17) C(18) -1.0(4) C(16) C(17) C(18) C(19) 0.5(4) C(16) C(17) C(18) C(22) -179.3(3) C(17) C(18) C(19) C(11) 178.8(2) C(17) C(18) C(19) C(20) 1.2(3) C(22) C(18) C(19) C(11) -1.3(4) C(22) C(18) C(19) C(20) -179.0(2) C(11) C(19) C(20) C(14) -1.7(3) C(11) C(19) C(20) C(15) 179.7(2) C(18) C(19) C(20) C(14) 176.1(2) C(18) C(19) C(20) C(15) -2.4(3) #------------------------------------------------------------------------------ _publ_contact_author_name 'Dr. Hirohito Tsue' _publ_contact_author_address ; Division of Material Science Graduate School of Environmental Earth Science Hokkaido University Kita 10, Nishi 5, Kita-ku Sapporo 060-0810 Japan ; _publ_contact_author_email 'tsue@ees.hokudai.ac.jp' _publ_contact_author_fax '81 11 757 5995' _publ_contact_author_phone '81 11 706 5288' _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_journal 'J. Chem. Soc., Perkin Trans. 1' _publ_requested_category ? _publ_requested_coeditor_name ? _publ_section_title ; 8,8'-Dialkyl-1,1'-biisoquinoline: preparation, absolute configuration and unexpected enantiomerization behaviour ; _publ_section_title_footnote ; ENTER FOOTNOTE TO TITLE OF PAPER ; loop_ _publ_author_name ' FIRST AUTHORS NAME ' _publ_author_footnote ' ' _publ_author_address ; FIRST AUTHORS ADDRESS ; _publ_section_synopsis ; ENTER SYNOPSIS ; _publ_section_abstract ; ENTER ABSTRACT ; _publ_section_comment ; ENTER TEXT ; _publ_section_acknowledgements ; ENTER ACKNOWLEDGEMENTS ; _publ_section_experimental ; ENTER EXPERIMENTAL SECTION ; _publ_section_references ; ENTER OTHER REFERENCES Main, P., Hull, S. E., Lessinger, L., Germain, G., Declercq, J. -P. and Woolfson, M. M. (1978). MULTAN. A Program for the Automatic Solution of Crystal Styrucutres from X-ray Diffraction Data. Univ. of york, England, and Louvain, Belgium. Sakurai, T., and Kobayashi, K. (1979). Rikagaku Kenkyusho Hokoku, 55, 69-77 (in Japanese) ; _publ_section_table_legends ; ENTER TABLE LEGENDS ; _publ_section_figure_captions ; ENTER FIGURE CAPTIONS ; _publ_section_exptl_prep ; ENTER COMPOUND PREPARATION DETAILS ; _publ_section_exptl_refinement ; ENTER SPECIAL DETAILS OF THE REFINEMENT ; #===END data_2 #8,8'-diethyl-1,1'-biisoquinoline #------------------------------------------------------------------------------ _audit_creation_date 'Thu May 27 16:22:10 1999' _audit_creation_method 'from TEXRAY.INF file' _audit_update_record ? #------------------------------------------------------------------------------ _computing_data_collection 'CAD4 express' _computing_cell_refinement 'CAD4 express' _computing_data_reduction 'teXsan' _computing_structure_solution SAPI91 _computing_structure_refinement 'teXsan' _computing_publication_material 'teXsan' _computing_molecular_graphics ? #------------------------------------------------------------------------------ _chemical_compound_source ? _chemical_name_common ? _chemical_formula_weight 312.41 _chemical_formula_analytical ? _chemical_formula_sum 'C22 H20 N2 ' _chemical_formula_moiety 'C22 H20 N2 ' _chemical_formula_structural ? _chemical_melting_point ? #------------------------------------------------------------------------------ _cell_length_a 21.343(3) _cell_length_b 20.316(2) _cell_length_c 7.5398(7) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 3269.3(5) _cell_formula_units_Z 8 _cell_measurement_temperature 296.7 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 18.8 _cell_measurement_theta_max 23.4 #------------------------------------------------------------------------------ _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a ' _symmetry_Int_Tables_number 61 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2+x,1/2-y,-z -x,1/2+y,1/2-z 1/2-x,-y,1/2+z -x,-y,-z 1/2-x,1/2+y,z x,1/2-y,1/2+z 1/2+x,y,1/2-z #------------------------------------------------------------------------------ _exptl_crystal_description 'prism' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.790 _exptl_crystal_size_mid 0.370 _exptl_crystal_size_min 0.320 _exptl_crystal_density_diffrn 1.269 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1328.00 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details Tompa_analytical _exptl_absorpt_correction_T_min 0.993 _exptl_absorpt_correction_T_max 0.994 _exptl_special_details ; ? ; #------------------------------------------------------------------------------ _diffrn_special_details ; ? ; _diffrn_ambient_temperature 296.7 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'CAD4 sealed tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device_type 'Enraf nonius CAD4' _diffrn_measurement_method \w _diffrn_standards_number 3 _diffrn_standards_interval_count 120 _diffrn_standards_decay_% -0.09 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -9 6 2 7 -6 3 5 9 2 _diffrn_reflns_number 7392 _reflns_number_total 3748 _reflns_number_gt 2200 _reflns_observed_criterion >2.0sigma(I) _diffrn_reflns_av_R_equivalents 0.037 _diffrn_reflns_av_sigmaI/netI 0.101 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.86 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 -0.03089 _diffrn_orient_matrix_UB_12 0.03692 _diffrn_orient_matrix_UB_13 -0.00216 _diffrn_orient_matrix_UB_21 0.03488 _diffrn_orient_matrix_UB_22 0.03209 _diffrn_orient_matrix_UB_23 -0.01841 _diffrn_orient_matrix_UB_31 -0.00436 _diffrn_orient_matrix_UB_32 -0.00508 _diffrn_orient_matrix_UB_33 -0.13134 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'H' 'H' 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; 'N' 'N' 0.006 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ 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_calc_flag N(1) N 0.13773(6) 0.46476(7) 0.7693(2) 0.0470(4) Uani 1.00 d N(1') N 0.10895(6) 0.48425(6) 0.3819(2) 0.0433(4) Uani 1.00 d C(1) C 0.15110(7) 0.43003(7) 0.6257(2) 0.0360(4) Uani 1.00 d C(1') C 0.09898(6) 0.43479(7) 0.4913(2) 0.0345(4) Uani 1.00 d C(2) C 0.18201(8) 0.47193(9) 0.8974(3) 0.0527(6) Uani 1.00 d C(2') C 0.06381(8) 0.50041(9) 0.2622(2) 0.0461(5) Uani 1.00 d C(3) C 0.23961(8) 0.44562(9) 0.8850(3) 0.0493(5) Uani 1.00 d C(3') C 0.00916(8) 0.46812(8) 0.2498(2) 0.0432(5) Uani 1.00 d C(4) C 0.31616(8) 0.38003(9) 0.7208(3) 0.0498(5) Uani 1.00 d C(4') C -0.05960(8) 0.37870(10) 0.3449(3) 0.0485(5) Uani 1.00 d C(5) C 0.33155(8) 0.34485(9) 0.5756(3) 0.0558(6) Uani 1.00 d C(5') C -0.07052(8) 0.32613(10) 0.4499(3) 0.0540(5) Uani 1.00 d C(6) C 0.28802(8) 0.33478(9) 0.4395(3) 0.0491(5) Uani 1.00 d C(6') C -0.02623(8) 0.30746(9) 0.5778(3) 0.0504(5) Uani 1.00 d C(7) C 0.22804(7) 0.35995(7) 0.4448(2) 0.0376(4) Uani 1.00 d C(7') C 0.02946(7) 0.34046(8) 0.6029(2) 0.0395(4) Uani 1.00 d C(8) C 0.25565(7) 0.40806(7) 0.7350(2) 0.0401(4) Uani 1.00 d C(8') C -0.00280(7) 0.41395(7) 0.3609(2) 0.0382(4) Uani 1.00 d C(9) C 0.21082(6) 0.39875(7) 0.5970(2) 0.0335(4) Uani 1.00 d C(9') C 0.04283(6) 0.39552(7) 0.4901(2) 0.0337(4) Uani 1.00 d C(10) C 0.18299(9) 0.34466(10) 0.2961(2) 0.0476(5) Uani 1.00 d C(10') C 0.06906(9) 0.31777(9) 0.7574(3) 0.0481(5) Uani 1.00 d C(11) C 0.2064(1) 0.2967(1) 0.1561(3) 0.0633(7) Uani 1.00 d C(11') C 0.0470(1) 0.3488(1) 0.9306(3) 0.0600(7) Uani 1.00 d H(2) H 0.1700(8) 0.4975(9) 1.003(3) 0.061(5) Uiso 1.00 calc H(2') H 0.0734(8) 0.5383(9) 0.187(2) 0.059(5) Uiso 1.00 calc H(3) H 0.2691(8) 0.4536(9) 0.977(2) 0.062(5) Uiso 1.00 calc H(3') H -0.0214(8) 0.4819(8) 0.162(3) 0.059(5) Uiso 1.00 calc H(4) H 0.3458(8) 0.3889(8) 0.819(2) 0.059(5) Uiso 1.00 calc H(4') H -0.0905(8) 0.3946(8) 0.253(2) 0.061(5) Uiso 1.00 calc H(5) H 0.3738(8) 0.3265(9) 0.559(2) 0.068(5) Uiso 1.00 calc H(5') H -0.1089(8) 0.2983(8) 0.436(2) 0.055(5) Uiso 1.00 calc H(6) H 0.3007(8) 0.3086(9) 0.334(2) 0.056(5) Uiso 1.00 calc H(6') H -0.0324(7) 0.2700(9) 0.654(2) 0.056(5) Uiso 1.00 calc H(101) H 0.1430(9) 0.3281(9) 0.346(2) 0.067(6) Uiso 1.00 calc H(101') H 0.0648(8) 0.2706(9) 0.764(2) 0.056(5) Uiso 1.00 calc H(102) H 0.1712(8) 0.3869(9) 0.240(2) 0.062(6) Uiso 1.00 calc H(102') H 0.1144(8) 0.3270(8) 0.739(2) 0.055(5) Uiso 1.00 calc H(111) H 0.245(1) 0.316(1) 0.098(3) 0.081(7) Uiso 1.00 calc H(111') H 0.0522(9) 0.397(1) 0.924(3) 0.075(6) Uiso 1.00 calc H(112) H 0.174(1) 0.291(1) 0.061(3) 0.087(7) Uiso 1.00 calc H(112') H 0.0696(10) 0.333(1) 1.031(3) 0.082(7) Uiso 1.00 calc H(113) H 0.2199(8) 0.253(1) 0.209(3) 0.075(6) Uiso 1.00 calc H(113') H 0.001(1) 0.336(1) 0.957(3) 0.097(7) Uiso 1.00 calc loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 N(1) 0.0404(7) 0.0522(8) 0.0485(9) 0.0015(6) -0.0017(7) -0.0109(7) N(1') 0.0347(7) 0.0444(8) 0.0509(9) 0.0024(6) 0.0003(6) 0.0058(7) C(1) 0.0317(8) 0.0354(8) 0.0409(9) -0.0018(6) 0.0001(7) -0.0011(7) C(1') 0.0299(7) 0.0356(7) 0.0381(9) 0.0048(6) 0.0027(7) -0.0039(7) C(2) 0.051(1) 0.059(1) 0.048(1) -0.0017(9) -0.0036(9) -0.0152(9) C(2') 0.0431(9) 0.0485(10) 0.047(1) 0.0050(8) 0.0008(8) 0.0073(9) C(3) 0.046(1) 0.055(1) 0.047(1) -0.0079(8) -0.0121(9) -0.0041(9) C(3') 0.0393(9) 0.0532(10) 0.0371(9) 0.0092(8) -0.0024(8) -0.0009(8) C(4) 0.0346(9) 0.050(1) 0.065(1) -0.0007(7) -0.0098(9) 0.0082(9) C(4') 0.0350(9) 0.062(1) 0.048(1) -0.0012(8) -0.0031(8) -0.0133(10) C(5) 0.0312(9) 0.054(1) 0.082(1) 0.0072(8) -0.0014(10) 0.004(1) C(5') 0.0395(10) 0.060(1) 0.063(1) -0.0132(8) 0.0041(9) -0.015(1) C(6) 0.0388(9) 0.0476(10) 0.061(1) 0.0055(7) 0.0104(9) -0.0003(9) C(6') 0.050(1) 0.0443(10) 0.057(1) -0.0067(8) 0.0113(9) -0.0042(9) C(7) 0.0343(8) 0.0350(8) 0.0435(9) -0.0001(6) 0.0044(7) 0.0047(7) C(7') 0.0391(9) 0.0375(8) 0.0420(10) 0.0023(7) 0.0089(7) -0.0060(7) C(8) 0.0341(8) 0.0386(8) 0.0477(10) -0.0059(6) -0.0058(7) 0.0059(8) C(8') 0.0324(8) 0.0465(9) 0.0357(8) 0.0048(7) 0.0023(7) -0.0110(7) C(9) 0.0294(7) 0.0313(7) 0.0399(9) -0.0035(6) 0.0005(7) 0.0058(7) C(9') 0.0289(7) 0.0373(8) 0.0348(9) 0.0039(6) 0.0039(6) -0.0072(7) C(10) 0.046(1) 0.052(1) 0.044(1) 0.0090(8) -0.0001(9) -0.0069(9) C(10') 0.047(1) 0.0409(9) 0.056(1) 0.0025(8) 0.0033(9) 0.0074(9) C(11) 0.065(1) 0.068(1) 0.057(1) 0.012(1) 0.002(1) -0.020(1) C(11') 0.066(1) 0.069(1) 0.045(1) 0.000(1) 0.001(1) 0.005(1) #------------------------------------------------------------------------------ _refine_special_details ; Refinement based on F against all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F, conventional R-factors (R) are calculated on F, with F set to zero for negative F. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. thus the refinement was done using all reflections. ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00078|Fo|^2^]' _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method 'Zachariasen(1967) type 2 Gaussian isotropic' _refine_ls_extinction_coef 0.003(1) _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 2200 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.0367 _refine_ls_R_factor_gt 0.0367 _refine_ls_wR_factor_all 0.0596 _refine_ls_wR_factor_ref 0.0466 _refine_ls_wR_factor_gt 0.0466 _refine_ls_goodness_of_fit_all 1.165 _refine_ls_goodness_of_fit_ref 1.226 _refine_ls_shift/su_max 0.0100 _refine_ls_shift/su_mean 0.0010 _refine_diff_density_min -0.16 _refine_diff_density_max 0.14 #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag N(1) C(1) 1.323(2) 1_555 1_555 yes N(1) C(2) 1.359(2) 1_555 1_555 yes N(1') C(1') 1.318(2) 1_555 1_555 yes N(1') C(2') 1.360(2) 1_555 1_555 yes C(1) C(1') 1.508(2) 1_555 1_555 yes C(1) C(9) 1.441(2) 1_555 1_555 yes C(1') C(9') 1.440(2) 1_555 1_555 yes C(2) C(3) 1.344(2) 1_555 1_555 yes C(2') C(3') 1.342(2) 1_555 1_555 yes C(3) C(8) 1.406(2) 1_555 1_555 yes C(3') C(8') 1.406(2) 1_555 1_555 yes C(4) C(5) 1.347(3) 1_555 1_555 yes C(4) C(8) 1.416(2) 1_555 1_555 yes C(4') C(5') 1.350(3) 1_555 1_555 yes C(4') C(8') 1.413(2) 1_555 1_555 yes C(5) C(6) 1.400(3) 1_555 1_555 yes C(5') C(6') 1.402(3) 1_555 1_555 yes C(6) C(7) 1.379(2) 1_555 1_555 yes C(6') C(7') 1.378(2) 1_555 1_555 yes C(7) C(9) 1.440(2) 1_555 1_555 yes C(7) C(10) 1.510(2) 1_555 1_555 yes C(7') C(9') 1.434(2) 1_555 1_555 yes C(7') C(10') 1.512(2) 1_555 1_555 yes C(8) C(9) 1.426(2) 1_555 1_555 yes C(8') C(9') 1.427(2) 1_555 1_555 yes C(10) C(11) 1.520(3) 1_555 1_555 yes C(10') C(11') 1.525(3) 1_555 1_555 yes #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(1) N(1) C(2) 119.2(1) 1_555 1_555 1_555 yes C(1') N(1') C(2') 119.0(1) 1_555 1_555 1_555 yes N(1) C(1) C(1') 110.9(1) 1_555 1_555 1_555 yes N(1) C(1) C(9) 123.3(1) 1_555 1_555 1_555 yes C(1') C(1) C(9) 125.5(1) 1_555 1_555 1_555 yes N(1') C(1') C(1) 110.5(1) 1_555 1_555 1_555 yes N(1') C(1') C(9') 123.6(1) 1_555 1_555 1_555 yes C(1) C(1') C(9') 125.7(1) 1_555 1_555 1_555 yes N(1) C(2) C(3) 123.0(2) 1_555 1_555 1_555 yes N(1) C(2) H(2) 116(1) 1_555 1_555 1_555 no C(3) C(2) H(2) 120(1) 1_555 1_555 1_555 no N(1') C(2') C(3') 123.0(2) 1_555 1_555 1_555 yes N(1') C(2') H(2') 115(1) 1_555 1_555 1_555 no C(3') C(2') H(2') 121(1) 1_555 1_555 1_555 no C(2) C(3) C(8) 119.6(2) 1_555 1_555 1_555 yes C(2) C(3) H(3) 119(1) 1_555 1_555 1_555 no C(8) C(3) H(3) 121(1) 1_555 1_555 1_555 no C(2') C(3') C(8') 119.9(2) 1_555 1_555 1_555 yes C(2') C(3') H(3') 119.5(10) 1_555 1_555 1_555 no C(8') C(3') H(3') 120.6(10) 1_555 1_555 1_555 no C(5) C(4) C(8) 119.8(2) 1_555 1_555 1_555 yes C(5) C(4) H(4) 123(1) 1_555 1_555 1_555 no C(8) C(4) H(4) 116(1) 1_555 1_555 1_555 no C(5') C(4') C(8') 119.9(2) 1_555 1_555 1_555 yes C(5') C(4') H(4') 122(1) 1_555 1_555 1_555 no C(8') C(4') H(4') 117(1) 1_555 1_555 1_555 no C(4) C(5) C(6) 120.8(2) 1_555 1_555 1_555 yes C(4) C(5) H(5) 121(1) 1_555 1_555 1_555 no C(6) C(5) H(5) 117(1) 1_555 1_555 1_555 no C(4') C(5') C(6') 120.1(2) 1_555 1_555 1_555 yes C(4') C(5') H(5') 121(1) 1_555 1_555 1_555 no C(6') C(5') H(5') 118(1) 1_555 1_555 1_555 no C(5) C(6) C(7) 122.7(2) 1_555 1_555 1_555 yes C(5) C(6) H(6) 119.0(10) 1_555 1_555 1_555 no C(7) C(6) H(6) 118.3(10) 1_555 1_555 1_555 no C(5') C(6') C(7') 123.0(2) 1_555 1_555 1_555 yes C(5') C(6') H(6') 122.1(10) 1_555 1_555 1_555 no C(7') C(6') H(6') 114.9(10) 1_555 1_555 1_555 no C(6) C(7) C(9) 117.6(1) 1_555 1_555 1_555 yes C(6) C(7) C(10) 119.6(1) 1_555 1_555 1_555 yes C(9) C(7) C(10) 122.8(1) 1_555 1_555 1_555 yes C(6') C(7') C(9') 118.0(2) 1_555 1_555 1_555 yes C(6') C(7') C(10') 116.1(2) 1_555 1_555 1_555 yes C(9') C(7') C(10') 125.7(1) 1_555 1_555 1_555 yes C(3) C(8) C(4) 120.1(2) 1_555 1_555 1_555 yes C(3) C(8) C(9) 119.7(1) 1_555 1_555 1_555 yes C(4) C(8) C(9) 120.2(2) 1_555 1_555 1_555 yes C(3') C(8') C(4') 120.1(2) 1_555 1_555 1_555 yes C(3') C(8') C(9') 119.2(1) 1_555 1_555 1_555 yes C(4') C(8') C(9') 120.7(2) 1_555 1_555 1_555 yes C(1) C(9) C(7) 126.0(1) 1_555 1_555 1_555 yes C(1) C(9) C(8) 115.2(1) 1_555 1_555 1_555 yes C(7) C(9) C(8) 118.9(1) 1_555 1_555 1_555 yes C(1') C(9') C(7') 126.5(1) 1_555 1_555 1_555 yes C(1') C(9') C(8') 115.3(1) 1_555 1_555 1_555 yes C(7') C(9') C(8') 118.3(1) 1_555 1_555 1_555 yes C(7) C(10) C(11) 116.0(2) 1_555 1_555 1_555 yes C(7) C(10) H(101) 109(1) 1_555 1_555 1_555 no C(7) C(10) H(102) 107(1) 1_555 1_555 1_555 no C(11) C(10) H(101) 109(1) 1_555 1_555 1_555 no C(11) C(10) H(102) 109(1) 1_555 1_555 1_555 no H(101) C(10) H(102) 103(1) 1_555 1_555 1_555 no C(7') C(10') C(11') 111.2(1) 1_555 1_555 1_555 yes C(7') C(10') H(101' 106.7(10) 1_555 1_555 1_555 no C(7') C(10') H(102' 112(1) 1_555 1_555 1_555 no C(11') C(10') H(101' 109(1) 1_555 1_555 1_555 no C(11') C(10') H(102' 109(1) 1_555 1_555 1_555 no H(101' C(10') H(102' 106(1) 1_555 1_555 1_555 no C(10) C(11) H(111) 108(1) 1_555 1_555 1_555 no C(10) C(11) H(112) 110(1) 1_555 1_555 1_555 no C(10) C(11) H(113) 112(1) 1_555 1_555 1_555 no H(111) C(11) H(112) 107(1) 1_555 1_555 1_555 no H(111) C(11) H(113) 106(1) 1_555 1_555 1_555 no H(112) C(11) H(113) 111(1) 1_555 1_555 1_555 no C(10') C(11') H(111' 109(1) 1_555 1_555 1_555 no C(10') C(11') H(112' 112(1) 1_555 1_555 1_555 no C(10') C(11') H(113' 110(1) 1_555 1_555 1_555 no H(111' C(11') H(112' 108(1) 1_555 1_555 1_555 no H(111' C(11') H(113' 111(1) 1_555 1_555 1_555 no H(112' C(11') H(113' 104(1) 1_555 1_555 1_555 no #------------------------------------------------------------------------------ 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 N(1) C(1) C(1') N(1') 91.0(2) 1_555 1_555 1_555 1_555 yes N(1) C(1) C(1') C(9') -83.5(2) 1_555 1_555 1_555 1_555 yes N(1) C(1) C(9) C(7) 179.4(1) 1_555 1_555 1_555 1_555 yes N(1) C(1) C(9) C(8) -0.4(2) 1_555 1_555 1_555 1_555 yes N(1) C(2) C(3) C(8) -0.8(3) 1_555 1_555 1_555 1_555 yes N(1') C(1') C(1) C(9) -82.2(2) 1_555 1_555 1_555 1_555 yes N(1') C(1') C(9') C(7') 178.8(1) 1_555 1_555 1_555 1_555 yes N(1') C(1') C(9') C(8') -0.4(2) 1_555 1_555 1_555 1_555 yes N(1') C(2') C(3') C(8') -1.5(3) 1_555 1_555 1_555 1_555 yes C(1) N(1) C(2) C(3) 0.5(3) 1_555 1_555 1_555 1_555 yes C(1) C(1') N(1') C(2') -173.5(1) 1_555 1_555 1_555 1_555 yes C(1) C(1') C(9') C(7') -7.4(2) 1_555 1_555 1_555 1_555 yes C(1) C(1') C(9') C(8') 173.4(1) 1_555 1_555 1_555 1_555 yes C(1) C(9) C(7) C(6) 178.9(1) 1_555 1_555 1_555 1_555 yes C(1) C(9) C(7) C(10) -2.7(2) 1_555 1_555 1_555 1_555 yes C(1) C(9) C(8) C(3) 0.1(2) 1_555 1_555 1_555 1_555 yes C(1) C(9) C(8) C(4) -179.5(1) 1_555 1_555 1_555 1_555 yes C(1') N(1') C(2') C(3') -0.1(2) 1_555 1_555 1_555 1_555 yes C(1') C(1) N(1) C(2) -173.2(1) 1_555 1_555 1_555 1_555 yes C(1') C(1) C(9) C(7) -8.2(2) 1_555 1_555 1_555 1_555 yes C(1') C(1) C(9) C(8) 172.0(1) 1_555 1_555 1_555 1_555 yes C(1') C(9') C(7') C(6') -177.8(1) 1_555 1_555 1_555 1_555 yes C(1') C(9') C(7') C(10') 6.9(2) 1_555 1_555 1_555 1_555 yes C(1') C(9') C(8') C(3') -1.2(2) 1_555 1_555 1_555 1_555 yes C(1') C(9') C(8') C(4') 179.2(1) 1_555 1_555 1_555 1_555 yes C(2) N(1) C(1) C(9) 0.1(2) 1_555 1_555 1_555 1_555 yes C(2) C(3) C(8) C(4) -179.9(2) 1_555 1_555 1_555 1_555 yes C(2) C(3) C(8) C(9) 0.5(2) 1_555 1_555 1_555 1_555 yes C(2') N(1') C(1') C(9') 1.1(2) 1_555 1_555 1_555 1_555 yes C(2') C(3') C(8') C(4') -178.3(2) 1_555 1_555 1_555 1_555 yes C(2') C(3') C(8') C(9') 2.1(2) 1_555 1_555 1_555 1_555 yes C(3) C(8) C(4) C(5) -179.1(2) 1_555 1_555 1_555 1_555 yes C(3) C(8) C(9) C(7) -179.8(1) 1_555 1_555 1_555 1_555 yes C(3') C(8') C(4') C(5') 179.0(2) 1_555 1_555 1_555 1_555 yes C(3') C(8') C(9') C(7') 179.5(1) 1_555 1_555 1_555 1_555 yes C(4) C(5) C(6) C(7) 0.3(3) 1_555 1_555 1_555 1_555 yes C(4) C(8) C(9) C(7) 0.6(2) 1_555 1_555 1_555 1_555 yes C(4') C(5') C(6') C(7') -0.2(3) 1_555 1_555 1_555 1_555 yes C(4') C(8') C(9') C(7') 0.0(2) 1_555 1_555 1_555 1_555 yes C(5) C(4) C(8) C(9) 0.5(2) 1_555 1_555 1_555 1_555 yes C(5) C(6) C(7) C(9) 0.8(2) 1_555 1_555 1_555 1_555 yes C(5) C(6) C(7) C(10) -177.6(2) 1_555 1_555 1_555 1_555 yes C(5') C(4') C(8') C(9') -1.4(2) 1_555 1_555 1_555 1_555 yes C(5') C(6') C(7') C(9') -1.3(2) 1_555 1_555 1_555 1_555 yes C(5') C(6') C(7') C(10') 174.5(2) 1_555 1_555 1_555 1_555 yes C(6) C(5) C(4) C(8) -1.0(3) 1_555 1_555 1_555 1_555 yes C(6) C(7) C(9) C(8) -1.2(2) 1_555 1_555 1_555 1_555 yes C(6) C(7) C(10) C(11) 5.0(3) 1_555 1_555 1_555 1_555 yes C(6') C(5') C(4') C(8') 1.6(3) 1_555 1_555 1_555 1_555 yes C(6') C(7') C(9') C(8') 1.4(2) 1_555 1_555 1_555 1_555 yes C(6') C(7') C(10') C(11') -82.7(2) 1_555 1_555 1_555 1_555 yes C(8) C(9) C(7) C(10) 177.1(1) 1_555 1_555 1_555 1_555 yes C(8') C(9') C(7') C(10') -174.0(1) 1_555 1_555 1_555 1_555 yes C(9) C(1) C(1') C(9') 103.4(2) 1_555 1_555 1_555 1_555 yes C(9) C(7) C(10) C(11) -173.3(2) 1_555 1_555 1_555 1_555 yes C(9') C(7') C(10') C(11') 92.7(2) 1_555 1_555 1_555 1_555 yes #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag N(1) C(3') 3.422(2) 1_555 5_566 ? N(1') C(4) 3.411(2) 1_555 4_564 ? N(1') C(3) 3.532(2) 1_555 4_564 ? C(2') C(4) 3.544(3) 1_555 4_564 ? C(2') C(8') 3.577(2) 1_555 5_566 ? C(3') C(11') 3.510(3) 1_555 1_554 ? C(3') C(9') 3.571(2) 1_555 5_566 ? C(6) C(11) 3.584(3) 1_555 7_555 ? C(7) C(11) 3.590(3) 1_555 7_555 ? #------------------------------------------------------------------------------ _publ_contact_author_name 'Dr. Hirohito Tsue' _publ_contact_author_address ; Division of Material Science Graduate School of Environmental Earth Science Hokkaido University Kita 10, Nishi 5, Kita-ku Sapporo 060-0810 Japan ; _publ_contact_author_email 'tsue@ees.hokudai.ac.jp' _publ_contact_author_fax '81 11 757 5995' _publ_contact_author_phone '81 11 706 5288' _publ_contact_letter ; ? ; _publ_requested_journal 'J. Chem. Soc., Perkin Trans. 1' _publ_requested_category ? _publ_requested_coeditor_name ? _publ_section_title ; 8,8'-Dialkyl-1,1'-biisoquinoline: preparation, absolute configuration and unexpected enantiomerization behaviour ; _publ_section_title_footnote ; ENTER FOOTNOTE TO TITLE OF PAPER ; loop_ _publ_author_name ' FIRST AUTHORS NAME ' _publ_author_footnote ' ' _publ_author_address ; FIRST AUTHORS ADDRESS ; _publ_section_synopsis ; ENTER SYNOPSIS ; _publ_section_abstract ; ENTER ABSTRACT ; _publ_section_comment ; ENTER TEXT ; _publ_section_acknowledgements ; ENTER ACKNOWLEDGEMENTS ; _publ_section_experimental ; ENTER EXPERIMENTAL SECTION ; _publ_section_references ; ENTER OTHER REFERENCES Molecular Structure Corporation, Rigaku Corporation. (1998). teXsan. Single Crystal Structure Analysis Software. Version 1.9. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Rigaku, 3-9-12 Akishima, Tokyo, Japan. Zachariasen, W. H. (1967). Acta Cryst. 23, 558-564. ; _publ_section_table_legends ; ENTER TABLE LEGENDS ; _publ_section_figure_captions ; ENTER FIGURE CAPTIONS ; _publ_section_exptl_prep ; ENTER COMPOUND PREPARATION DETAILS ; _publ_section_exptl_refinement ; ENTER SPECIAL DETAILS OF THE REFINEMENT ;