# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Yoshinao Tamaru' 'Masanari Kimura' 'Keisuke Kojima' 'Masahiko Mori' 'Nahoko Mukai' _publ_contact_author_name 'Yoshinao Tamaru' _publ_contact_author_address ; Applied Chemistry, Faculty of Engineering, Nagasaki University 1-14 Bunkyo Nagasaki 852-8521 JAPAN ; _publ_contact_author_email TAMARU@NET.NAGASAKI-U.AC.JP _publ_requested_journal 'Chemical Communications' _publ_section_title ; Nickel catalyzed stereoselective conjugate addition of dimethylzinc upon aldimines across 1,?-dienynes ; _publ_section_references ; ENTER OTHER REFERENCES Molecular Structure Corporation, Rigaku Corporation. (2000). teXsan. Single Crystal Structure Analysis Software. Version 1.11. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Rigaku, 3-9-12 Akishima, Tokyo, Japan. ; #------------------------------------------------------------------------------ data_0460 _database_code_depnum_ccdc_archive 'CCDC 209610' #------------------------------------------------------------------------------ # CHEMICAL DATA _chemical_formula_sum 'C25 H31 N O2 ' _chemical_formula_moiety 'C25 H31 N O2 ' _chemical_formula_weight 377.53 _chemical_melting_point ? #------------------------------------------------------------------------------ # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z _cell_length_a 8.8531(8) _cell_length_b 10.122(2) _cell_length_c 12.351(2) _cell_angle_alpha 85.224(5) _cell_angle_beta 85.589(3) _cell_angle_gamma 76.189(2) _cell_volume 1069.2(3) _cell_formula_units_Z 2 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _cell_measurement_temperature 297.2 #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour clear _exptl_crystal_size_max 0.500 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_min 0.200 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.173 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(Jacobson, 1998)' _exptl_absorpt_correction_T_min 0.781 _exptl_absorpt_correction_T_max 0.985 #------------------------------------------------------------------------------ # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Quantum CCD/Rigaku AFC7' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 9132 _diffrn_reflns_av_R_equivalents 0.021 _diffrn_reflns_theta_max 27.45 _diffrn_measured_fraction_theta_max 0.9244 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.9244 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 #------------------------------------------------------------------------------ # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > -10.0 sigma(F^2^). The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 4501 _reflns_number_gt 2394 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0627 _refine_ls_wR_factor_ref 0.1450 _refine_ls_hydrogen_treatment ? _refine_ls_number_reflns 4498 _refine_ls_number_parameters 341 _refine_ls_goodness_of_fit_ref 1.638 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^) + (0.02000(Max(Fo^2^,0) + 2Fc^2^)/3)^2^]' _refine_ls_shift/su_max 0.0007 _refine_diff_density_max 0.55 _refine_diff_density_min -0.47 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? 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) ; O O 0.011 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O(1) O 0.2581(2) 0.2530(2) 0.9429(1) 0.0590(5) Uani 1.00 d . . . O(2) O -0.4070(4) 1.2984(3) 0.5898(4) 0.174(2) Uani 1.00 d . . . N(1) N -0.3014(2) 0.7791(2) 0.8032(2) 0.0528(6) Uani 1.00 d . . . C(1) C 0.2834(3) 0.1214(3) 0.8998(2) 0.0600(8) Uani 1.00 d . . . C(2) C 0.1582(3) 0.1177(3) 0.8250(2) 0.0543(8) Uani 1.00 d . . . C(3) C 0.1465(2) 0.2289(2) 0.7347(2) 0.0434(6) Uani 1.00 d . . . C(4) C 0.1414(2) 0.3662(2) 0.7773(2) 0.0442(7) Uani 1.00 d . . . C(5) C 0.2677(3) 0.3533(3) 0.8564(2) 0.0557(8) Uani 1.00 d . . . C(6) C 0.1383(2) 0.2083(3) 0.6301(2) 0.0526(7) Uani 1.00 d . . . C(7) C 0.1326(4) 0.3175(3) 0.5391(2) 0.085(1) Uani 1.00 d . . . C(8) C 0.1332(3) 0.0717(3) 0.5913(2) 0.0740(10) Uani 1.00 d . . . C(9) C -0.0185(3) 0.4258(2) 0.8294(2) 0.0504(7) Uani 1.00 d . . . C(10) C -0.1399(3) 0.4894(3) 0.7797(2) 0.0569(8) Uani 1.00 d . . . C(11) C -0.3016(3) 0.5397(3) 0.8295(2) 0.0548(8) Uani 1.00 d . . . C(12) C -0.3862(2) 0.6793(2) 0.7800(2) 0.0483(7) Uani 1.00 d . . . C(13) C -0.5574(2) 0.7107(2) 0.8197(2) 0.0453(7) Uani 1.00 d . . . C(14) C -0.6710(3) 0.7015(3) 0.7521(3) 0.0605(9) Uani 1.00 d . . . C(15) C -0.8275(3) 0.7234(3) 0.7911(3) 0.0688(10) Uani 1.00 d . . . C(16) C -0.8689(3) 0.7534(3) 0.8963(3) 0.0670(9) Uani 1.00 d . . . C(17) C -0.7574(3) 0.7641(3) 0.9635(3) 0.0658(9) Uani 1.00 d . . . C(18) C -0.6024(3) 0.7428(2) 0.9257(2) 0.0523(7) Uani 1.00 d . . . C(19) C -0.3310(2) 0.9099(2) 0.7527(2) 0.0494(7) Uani 1.00 d . . . C(20) C -0.4365(3) 0.9533(3) 0.6720(2) 0.0554(8) Uani 1.00 d . . . C(21) C -0.4566(4) 1.0819(3) 0.6207(3) 0.0707(10) Uani 1.00 d . . . C(22) C -0.3738(4) 1.1705(3) 0.6481(3) 0.088(1) Uani 1.00 d . . . C(23) C -0.2709(4) 1.1309(4) 0.7272(4) 0.089(1) Uani 1.00 d . . . C(24) C -0.2486(3) 1.0022(3) 0.7800(3) 0.0692(10) Uani 1.00 d . . . C(25) C -0.3141(9) 1.3597(7) 0.5651(6) 0.193(3) Uani 1.00 d . . . H(1) H 0.286(3) 0.058(3) 0.965(2) 0.080(8) Uiso 1.00 calc . . . H(2) H 0.391(3) 0.103(3) 0.861(2) 0.073(8) Uiso 1.00 calc . . . H(3) H 0.189(3) 0.029(3) 0.794(2) 0.072(8) Uiso 1.00 calc . . . H(4) H 0.055(3) 0.128(3) 0.869(2) 0.075(8) Uiso 1.00 calc . . . H(5) H 0.160(2) 0.429(2) 0.718(2) 0.046(6) Uiso 1.00 calc . . . H(6) H 0.255(3) 0.435(3) 0.892(2) 0.073(8) Uiso 1.00 calc . . . H(7) H 0.376(3) 0.329(2) 0.816(2) 0.059(7) Uiso 1.00 calc . . . H(8) H 0.0432 0.3906 0.5511 0.1059 Uiso 1.00 calc . . . H(9) H 0.2238 0.3535 0.5373 0.1059 Uiso 1.00 calc . . . H(10) H 0.1276 0.2822 0.4714 0.1059 Uiso 1.00 calc . . . H(11) H 0.1285 0.0784 0.5130 0.0887 Uiso 1.00 calc . . . H(12) H 0.2250 0.0046 0.6093 0.0887 Uiso 1.00 calc . . . H(13) H 0.0445 0.0431 0.6227 0.0887 Uiso 1.00 calc . . . H(14) H -0.032(3) 0.421(3) 0.901(2) 0.087(10) Uiso 1.00 calc . . . H(15) H -0.129(4) 0.500(4) 0.702(3) 0.12(1) Uiso 1.00 calc . . . H(16) H -0.295(2) 0.546(2) 0.911(2) 0.059(7) Uiso 1.00 calc . . . H(17) H -0.363(3) 0.478(3) 0.820(2) 0.085(9) Uiso 1.00 calc . . . H(18) H -0.384(2) 0.672(2) 0.698(2) 0.044(6) Uiso 1.00 calc . . . H(19) H -0.645(3) 0.679(3) 0.673(2) 0.066(7) Uiso 1.00 calc . . . H(20) H -0.899(3) 0.718(3) 0.742(2) 0.084(9) Uiso 1.00 calc . . . H(21) H -0.983(3) 0.767(3) 0.917(2) 0.073(8) Uiso 1.00 calc . . . H(22) H -0.787(3) 0.789(3) 1.039(3) 0.094(10) Uiso 1.00 calc . . . H(23) H -0.526(3) 0.752(3) 0.975(2) 0.068(8) Uiso 1.00 calc . . . H(24) H -0.278(3) 0.768(3) 0.866(2) 0.08(1) Uiso 1.00 calc . . . H(25) H -0.496(3) 0.894(2) 0.652(2) 0.054(7) Uiso 1.00 calc . . . H(26) H -0.526(3) 1.110(3) 0.567(2) 0.087(10) Uiso 1.00 calc . . . H(27) H -0.210(4) 1.182(3) 0.747(3) 0.10(1) Uiso 1.00 calc . . . H(28) H -0.175(3) 0.969(3) 0.831(2) 0.080(9) Uiso 1.00 calc . . . H(29) H -0.2315 1.3118 0.5128 0.2268 Uiso 1.00 calc . . . H(30) H -0.2584 1.3795 0.6230 0.2268 Uiso 1.00 calc . . . H(31) H -0.3557 1.4475 0.5254 0.2268 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 O(1) 0.062(1) 0.053(1) 0.059(1) -0.0031(8) -0.0113(8) -0.0068(9) O(2) 0.133(3) 0.081(2) 0.286(5) -0.027(2) 0.053(3) 0.052(2) N(1) 0.047(1) 0.054(1) 0.058(1) -0.0144(9) -0.006(1) 0.003(1) C(1) 0.069(2) 0.045(2) 0.056(2) 0.004(1) -0.003(1) 0.000(1) C(2) 0.065(2) 0.040(2) 0.055(2) -0.010(1) 0.002(1) -0.004(1) C(3) 0.035(1) 0.040(1) 0.052(1) -0.0055(9) 0.0019(10) -0.003(1) C(4) 0.040(1) 0.037(1) 0.052(1) -0.0051(9) 0.003(1) 0.002(1) C(5) 0.051(2) 0.047(2) 0.068(2) -0.011(1) -0.003(1) -0.007(1) C(6) 0.047(1) 0.056(2) 0.050(2) -0.004(1) 0.000(1) -0.005(1) C(7) 0.097(2) 0.089(2) 0.058(2) -0.006(2) -0.007(2) 0.007(2) C(8) 0.071(2) 0.081(2) 0.072(2) -0.014(1) -0.002(1) -0.030(2) C(9) 0.046(1) 0.044(1) 0.055(2) -0.001(1) 0.004(1) -0.001(1) C(10) 0.044(1) 0.064(2) 0.057(2) 0.000(1) 0.001(1) -0.014(1) C(11) 0.042(1) 0.048(2) 0.068(2) 0.001(1) 0.002(1) -0.006(1) C(12) 0.041(1) 0.049(1) 0.052(2) -0.004(1) -0.001(1) -0.007(1) C(13) 0.039(1) 0.036(1) 0.059(2) -0.0047(9) -0.001(1) -0.003(1) C(14) 0.053(2) 0.055(2) 0.075(2) -0.011(1) -0.010(1) -0.011(1) C(15) 0.047(2) 0.054(2) 0.109(3) -0.015(1) -0.022(2) 0.002(2) C(16) 0.043(2) 0.049(2) 0.103(2) -0.005(1) 0.004(2) 0.011(2) C(17) 0.049(2) 0.059(2) 0.080(2) -0.003(1) 0.010(1) 0.003(2) C(18) 0.041(1) 0.051(2) 0.060(2) -0.005(1) 0.001(1) -0.002(1) C(19) 0.036(1) 0.049(2) 0.059(1) -0.006(1) 0.009(1) -0.002(1) C(20) 0.052(1) 0.056(2) 0.055(2) -0.009(1) 0.003(1) 0.002(1) C(21) 0.062(2) 0.065(2) 0.072(2) 0.002(1) 0.009(2) 0.016(2) C(22) 0.070(2) 0.049(2) 0.130(3) -0.003(2) 0.026(2) 0.018(2) C(23) 0.068(2) 0.061(2) 0.141(3) -0.024(2) 0.009(2) -0.009(2) C(24) 0.054(2) 0.058(2) 0.096(2) -0.015(1) -0.002(2) -0.004(2) C(25) 0.264(7) 0.152(5) 0.192(6) -0.105(5) -0.040(5) 0.013(5) #------------------------------------------------------------------------------ _computing_data_collection D*TREK _computing_cell_refinement D*TREK _computing_data_reduction 'teXsan Ver. 1.11' _computing_structure_solution SIR92 _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.11' _computing_molecular_graphics ? #------------------------------------------------------------------------------ _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 O(1) C(1) 1.437(3) . . yes O(1) C(5) 1.424(3) . . yes O(2) C(22) 1.406(4) . . yes O(2) C(25) 1.152(6) . . yes N(1) C(12) 1.452(3) . . yes N(1) C(19) 1.390(3) . . yes C(1) C(2) 1.505(4) . . yes C(2) C(3) 1.508(3) . . yes C(3) C(4) 1.516(3) . . yes C(3) C(6) 1.336(3) . . yes C(4) C(5) 1.516(3) . . yes C(4) C(9) 1.517(3) . . yes C(6) C(7) 1.504(4) . . yes C(6) C(8) 1.512(4) . . yes C(9) C(10) 1.285(3) . . yes C(10) C(11) 1.501(3) . . yes C(11) C(12) 1.534(3) . . yes C(12) C(13) 1.523(3) . . yes C(13) C(14) 1.380(3) . . yes C(13) C(18) 1.381(3) . . yes C(14) C(15) 1.403(4) . . yes C(15) C(16) 1.362(4) . . yes C(16) C(17) 1.366(4) . . yes C(17) C(18) 1.388(3) . . yes C(19) C(20) 1.391(3) . . yes C(19) C(24) 1.391(4) . . yes C(20) C(21) 1.378(4) . . yes C(21) C(22) 1.363(4) . . yes C(22) C(23) 1.358(5) . . yes C(23) C(24) 1.384(4) . . 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) O(1) C(5) 109.6(2) . . . yes C(22) O(2) C(25) 123.1(5) . . . yes C(12) N(1) C(19) 122.1(2) . . . yes O(1) C(1) C(2) 111.0(2) . . . yes C(1) C(2) C(3) 111.4(2) . . . yes C(2) C(3) C(4) 111.9(2) . . . yes C(2) C(3) C(6) 123.6(2) . . . yes C(4) C(3) C(6) 124.4(2) . . . yes C(3) C(4) C(5) 110.5(2) . . . yes C(3) C(4) C(9) 110.5(2) . . . yes C(5) C(4) C(9) 111.4(2) . . . yes O(1) C(5) C(4) 111.9(2) . . . yes C(3) C(6) C(7) 123.9(2) . . . yes C(3) C(6) C(8) 123.0(2) . . . yes C(7) C(6) C(8) 113.1(2) . . . yes C(4) C(9) C(10) 126.5(3) . . . yes C(9) C(10) C(11) 127.0(3) . . . yes C(10) C(11) C(12) 113.6(2) . . . yes N(1) C(12) C(11) 108.1(2) . . . yes N(1) C(12) C(13) 115.2(2) . . . yes C(11) C(12) C(13) 110.1(2) . . . yes C(12) C(13) C(14) 120.8(2) . . . yes C(12) C(13) C(18) 120.9(2) . . . yes C(14) C(13) C(18) 118.2(2) . . . yes C(13) C(14) C(15) 120.5(3) . . . yes C(14) C(15) C(16) 120.3(3) . . . yes C(15) C(16) C(17) 119.7(3) . . . yes C(16) C(17) C(18) 120.5(3) . . . yes C(13) C(18) C(17) 121.0(3) . . . yes N(1) C(19) C(20) 123.1(2) . . . yes N(1) C(19) C(24) 119.6(2) . . . yes C(20) C(19) C(24) 117.2(3) . . . yes C(19) C(20) C(21) 121.0(3) . . . yes C(20) C(21) C(22) 120.8(3) . . . yes O(2) C(22) C(21) 114.7(4) . . . yes O(2) C(22) C(23) 126.0(4) . . . yes C(21) C(22) C(23) 119.2(3) . . . yes C(22) C(23) C(24) 121.1(3) . . . yes C(19) C(24) C(23) 120.6(3) . . . yes #------------------------------------------------------------------------------ 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 O(1) C(1) C(2) C(3) 55.8(3) . . . . yes O(1) C(5) C(4) C(3) -55.2(3) . . . . yes O(1) C(5) C(4) C(9) 68.0(3) . . . . yes O(2) C(22) C(21) C(20) -179.5(3) . . . . yes O(2) C(22) C(23) C(24) 179.4(3) . . . . yes N(1) C(12) C(11) C(10) -63.7(3) . . . . yes N(1) C(12) C(13) C(14) 132.6(2) . . . . yes N(1) C(12) C(13) C(18) -50.5(3) . . . . yes N(1) C(19) C(20) C(21) -176.9(2) . . . . yes N(1) C(19) C(24) C(23) 177.0(3) . . . . yes C(1) O(1) C(5) C(4) 63.1(3) . . . . yes C(1) C(2) C(3) C(4) -48.1(3) . . . . yes C(1) C(2) C(3) C(6) 133.2(2) . . . . yes C(2) C(1) O(1) C(5) -63.1(3) . . . . yes C(2) C(3) C(4) C(5) 47.3(3) . . . . yes C(2) C(3) C(4) C(9) -76.4(2) . . . . yes C(2) C(3) C(6) C(7) -177.6(2) . . . . yes C(2) C(3) C(6) C(8) 2.6(3) . . . . yes C(3) C(4) C(9) C(10) -80.8(3) . . . . yes C(4) C(3) C(6) C(7) 3.9(3) . . . . yes C(4) C(3) C(6) C(8) -175.9(2) . . . . yes C(4) C(9) C(10) C(11) 175.1(3) . . . . yes C(5) C(4) C(3) C(6) -134.1(2) . . . . yes C(5) C(4) C(9) C(10) 156.0(3) . . . . yes C(6) C(3) C(4) C(9) 102.2(3) . . . . yes C(9) C(10) C(11) C(12) 140.8(3) . . . . yes C(10) C(11) C(12) C(13) 169.7(2) . . . . yes C(11) C(12) N(1) C(19) 167.9(2) . . . . yes C(11) C(12) C(13) C(14) -104.9(3) . . . . yes C(11) C(12) C(13) C(18) 72.0(3) . . . . yes C(12) N(1) C(19) C(20) -3.9(3) . . . . yes C(12) N(1) C(19) C(24) 178.6(2) . . . . yes C(12) C(13) C(14) C(15) 176.5(2) . . . . yes C(12) C(13) C(18) C(17) -176.5(2) . . . . yes C(13) C(12) N(1) C(19) -68.6(3) . . . . yes C(13) C(14) C(15) C(16) -0.3(4) . . . . yes C(13) C(18) C(17) C(16) 0.2(4) . . . . yes C(14) C(13) C(18) C(17) 0.5(4) . . . . yes C(14) C(15) C(16) C(17) 1.0(4) . . . . yes C(15) C(14) C(13) C(18) -0.4(4) . . . . yes C(15) C(16) C(17) C(18) -0.9(4) . . . . yes C(19) C(20) C(21) C(22) -0.2(4) . . . . yes C(19) C(24) C(23) C(22) 0.2(5) . . . . yes C(20) C(19) C(24) C(23) -0.6(4) . . . . yes C(20) C(21) C(22) C(23) -0.2(5) . . . . yes C(21) C(20) C(19) C(24) 0.7(4) . . . . yes C(21) C(22) O(2) C(25) -145.1(6) . . . . yes C(21) C(22) C(23) C(24) 0.2(5) . . . . yes C(23) C(22) O(2) C(25) 35.7(8) . . . . yes C(23) C(22) O(2) C(25) 35.7(8) . . . . 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 O(1) N(1) 3.169(3) . 2_567 ? O(1) C(18) 3.573(3) . 2_567 ? C(6) C(21) 3.505(4) . 1_645 ? #------------------------------------------------------------------------------ #------------------------------------------------------------------------------