Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2001 ---------- X-Sun-Data-Type: text X-Sun-Charset: us-ascii X-Sun-Content-Lines: 865 data_mgb63 _database_code_CSD 165269 #--------------------------------------------------------------------------- #-- _audit_creation_date '1999-03-19' _audit_creation_method 'by teXsan v1.8' _audit_update_record ; 1999-03 sample id is tk137a 1999-03-10 acw finishes report 2001-08-05 acw puts cif together ; #--------------------------------------------------------------------------- _publ_requested_journal ' ChemComm ' _journal_coden_Cambridge 182 _publ_requested_category ' CO ' _publ_contact_author_name ' Anthony C. Willis ' _publ_contact_author_address ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_coeditor_name ? _publ_contact_author_phone ' 61 2 6125 4109 ' _publ_contact_author_fax ' 61 2 6125 0750 ' _publ_contact_author_email ' willis@rsc.anu.edu.au' loop_ _publ_author_name _publ_author_address ' Martin G. Banwell ' ; Research School of Chemistry, Institute of Advanced Studies, Australian National University, Canberra, A. C. T. 0200, Australia ; ' Curtis F. Crasto ' ; Research School of Chemistry, Institute of Advanced Studies, Australian National University, Canberra, A. C. T. 0200, Australia ; ' Christopher J. Easton ' ; Research School of Chemistry, Institute of Advanced Studies, Australian National University, Canberra, A. C. T. 0200, Australia ; ' Tomislav Karoli ' ; Research School of Chemistry, Institute of Advanced Studies, Australian National University, Canberra, A. C. T. 0200, Australia ; ' Darren R. March ' ; Research School of Chemistry, Institute of Advanced Studies, Australian National University, Canberra, A. C. T. 0200, Australia ; ' Michael R. Nairn ' ; Research School of Chemistry, Institute of Advanced Studies, Australian National University, Canberra, A. C. T. 0200, Australia ; ' Peter J. O'Hanlon ' ; GlaxoSmithKline, New Frontiers Science Park, Harlow CM19 5AW, UK. ; ' Mark D. Oldham ' ; Research School of Chemistry, Institute of Advanced Studies, Australian National University, Canberra, A. C. T. 0200, Australia ; ' Anthony C. Willis ' ; Research School of Chemistry, Institute of Advanced Studies, Australian National University, Canberra, A. C. T. 0200, Australia ; ' Weimin Yue ' ; Research School of Chemistry, Institute of Advanced Studies, Australian National University, Canberra, A. C. T. 0200, Australia ; _publ_section_title ; Multi-component Assembly of the Bicyclic Core Associated with the tRNA Synthetase Inhibitors SB-203207 and SB-203208. Application to the Synthesis of Biologically Active Analogues ; _publ_section_title_footnote ' ENTER ANY FOOTNOTES TO TITLE ' _publ_section_abstract ; ENTER ABSTRACT ; _publ_section_exptl_refinement ; ENTER EXPERIMENTAL SECTION ; _publ_section_comment ; ENTER TEXT ; _publ_section_references ; teXsan: Single Crystal Structure Analysis Software. Version 1.8. Molecular Structure Corporation, The Woodlands, TX 77381, USA, 1997 de Meulenaer, J. & Tompa, H. (1965), Acta Cryst. 19, 1014. Zachariasen, W. H. (1967). Acta Cryst. 23, 558-564. Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. ; _publ_section_acknowledgements ; ENTER ACKNOWLEDGEMENTS ; _publ_section_table_legends ; ENTER TABLE LEGENDS ; _publ_section_figure_captions ; ENTER FIGURE CAPTIONS ; #--------------------------------------------------------------------------- #-- _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan (MSC, 1992-1997)' _computing_structure_solution ; SIR92 (Altomare, et. al. 1994) ; _computing_structure_refinement 'teXsan (MSC, 1992-1997)' _computing_publication_material 'teXsan (MSC, 1992-1997)' #--------------------------------------------------------------------------- #-- _cell_length_a 9.812(1) _cell_length_b 9.839(1) _cell_length_c 15.524(2) _cell_angle_alpha 77.24(1) _cell_angle_beta 71.55(1) _cell_angle_gamma 69.783(9) _cell_volume 1323.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 296.2 _cell_measurement_reflns_used 23 _cell_measurement_theta_min 50.9 _cell_measurement_theta_max 54.9 #--------------------------------------------------------------------------- #-- _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_Int_Tables_number 2 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x, -y, -z' #--------------------------------------------------------------------------- #-- _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _exptl_crystal_description 'rod' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.17 _exptl_crystal_density_diffrn 1.218 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 485.58 _chemical_formula_analytical ? _chemical_formula_sum 'C24 H37 N4 O6.50 ' _chemical_formula_moiety '2(C12 H18 N2 O3), 0.5(H2 O)' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 522.00 _exptl_absorpt_coefficient_mu 0.734 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; analytical (de Meulenaer & Tompa, 1965) ; _exptl_absorpt_correction_T_max 0.903 _exptl_absorpt_correction_T_min 0.830 _exptl_special_details ; The scan width was (1.60+0.30tan\q)\% with an \w scan speed of 32\% per minute (up to 5 scans to achieve I/\s(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1. Data can only be collected to 2theta 120 deg on a AFC6R diffractometer when the evacuated beam tunnel in used. Mass attenuation coefficients for absorption from International Tables for X-ray Crystallography, Vol IV (1974) Table 2.1C. ; #--------------------------------------------------------------------------- #-- _diffrn_special_details ; ? ; _diffrn_ambient_temperature 296.2 _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device_type 'Rigaku AFC6R' _diffrn_measurement_device_details ; Rigaku AFC6R diffractometer with extended arm and evacuated collimator and beam tunnel. Data cannot be collected beyond \y 60 deg in this configuration. ; _diffrn_measurement_method \w-2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% -0.36 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? ? ? ? ? ? ? _diffrn_reflns_number 4192 _reflns_number_total 3923 _reflns_number_gt 3106 _reflns_threshold_expression I>2.00\s(I) _diffrn_reflns_av_R_equivalents 0.04570 _diffrn_reflns_av_sigmaI/netI 0.040 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 60.04 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 0.05517 _diffrn_orient_matrix_UB_12 -0.05823 _diffrn_orient_matrix_UB_13 -0.05258 _diffrn_orient_matrix_UB_21 0.03035 _diffrn_orient_matrix_UB_22 0.08629 _diffrn_orient_matrix_UB_23 -0.03802 _diffrn_orient_matrix_UB_31 0.09329 _diffrn_orient_matrix_UB_32 -0.03288 _diffrn_orient_matrix_UB_33 0.02179 #--------------------------------------------------------------------------- #-- loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 48 0.017 0.009 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H 0 74 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; N 0 8 0.029 0.018 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; O 0 13 0.047 0.032 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #--------------------------------------------------------------------------- #-- 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_refinement_flags _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom O(8) -0.0381(2) 0.3701(2) 0.7500(2) 0.0716(7) 1.000 . Uani d ? O(10) -0.2426(3) 0.4273(3) 0.7026(2) 0.130(1) 1.000 . Uani d ? O(13) 0.1604(2) 0.8362(2) 0.9579(1) 0.0611(6) 1.000 . Uani d ? N(6) 0.2769(2) 0.4598(2) 0.8431(2) 0.0597(7) 1.000 . Uani d ? N(14) -0.0637(2) 0.9227(2) 0.9269(2) 0.0638(8) 1.000 . Uani d ? C(1) -0.0806(3) 0.5158(3) 0.7746(2) 0.0585(9) 1.000 . Uani d ? C(2) -0.1929(3) 0.5328(3) 0.8670(2) 0.069(1) 1.000 . Uani d ? C(3a) -0.0137(3) 0.6689(3) 0.8425(2) 0.0465(7) 1.000 . Uani d ? C(3) -0.1464(3) 0.6249(3) 0.9129(2) 0.0549(8) 1.000 . Uani d ? C(4) 0.0987(3) 0.6898(3) 0.8815(2) 0.0452(7) 1.000 . Uani d ? C(5) 0.2332(3) 0.5866(3) 0.8780(2) 0.0506(8) 1.000 . Uani d ? C(7a) 0.0573(3) 0.5474(3) 0.7808(2) 0.0532(8) 1.000 . Uani d ? C(7) 0.1645(3) 0.4161(3) 0.8224(2) 0.0593(9) 1.000 . Uani d ? C(9) -0.1308(4) 0.3402(3) 0.7163(2) 0.074(1) 1.000 . Uani d ? C(11) -0.0834(5) 0.1858(4) 0.7007(3) 0.114(2) 1.000 . Uani d ? C(12) 0.0681(3) 0.8198(3) 0.9242(2) 0.0477(7) 1.000 . Uani d ? C(15) 0.4139(3) 0.3469(4) 0.8540(2) 0.077(1) 1.000 . Uani d ? H(1) -0.1223 0.5851 0.7294 0.070 1.000 . Uiso c ? H(2) -0.1896 0.4401 0.9022 0.082 1.000 . Uiso c ? H(3) -0.2918 0.5808 0.8600 0.082 1.000 . Uiso c ? H(4) -0.1163 0.5696 0.9658 0.066 1.000 . Uiso c ? H(5) -0.2277 0.7094 0.9299 0.066 1.000 . Uiso c ? H(6) -0.0528 0.7575 0.8070 0.056 1.000 . Uiso c ? H(7) 0.3021 0.6049 0.9020 0.061 1.000 . Uiso c ? H(8) 0.1089 0.3737 0.8772 0.071 1.000 . Uiso c ? H(9) 0.2136 0.3463 0.7802 0.071 1.000 . Uiso c ? H(10) 0.1091 0.5829 0.7220 0.064 1.000 . Uiso c ? H(11) 0.0127 0.1634 0.6580 0.137 1.000 . Uiso c ? H(12) -0.0780 0.1245 0.7569 0.137 1.000 . Uiso c ? H(13) -0.1545 0.1703 0.6772 0.137 1.000 . Uiso c ? H(14) -0.1268 0.9119 0.9041 0.077 1.000 . Uiso c ? H(15) -0.0845 0.9990 0.9515 0.077 1.000 . Uiso c ? H(16) 0.4793 0.3891 0.8653 0.092 1.000 . Uiso c ? H(17) 0.3901 0.2761 0.9041 0.092 1.000 . Uiso c ? H(18) 0.4623 0.3014 0.7997 0.092 1.000 . Uiso c ? O(8Z) 0.5468(2) 0.2492(2) 0.4572(1) 0.0638(6) 1.000 . Uani d ? O(10Z) 0.7395(3) 0.3253(3) 0.4460(2) 0.112(1) 1.000 . Uani d ? O(13Z) 0.3622(2) 0.0104(2) 0.1151(1) 0.0569(6) 1.000 . Uani d ? N(6Z) 0.2553(2) 0.1243(3) 0.3706(2) 0.0620(7) 1.000 . Uani d ? N(14Z) 0.5783(2) 0.0668(3) 0.0687(2) 0.0684(8) 1.000 . Uani d ? C(1Z) 0.5962(3) 0.2342(3) 0.3594(2) 0.0535(8) 1.000 . Uani d ? C(2Z) 0.7226(3) 0.0962(3) 0.3366(2) 0.0635(9) 1.000 . Uani d ? C(3Z) 0.6759(3) 0.0256(3) 0.2762(2) 0.0618(9) 1.000 . Uani d ? C(3Y) 0.5414(3) 0.1420(3) 0.2489(2) 0.0472(7) 1.000 . Uani d ? C(4Z) 0.4323(3) 0.0902(3) 0.2243(2) 0.0448(7) 1.000 . Uani d ? C(5Z) 0.2998(3) 0.0880(3) 0.2858(2) 0.0501(8) 1.000 . Uani d ? C(7Z) 0.3629(3) 0.1504(3) 0.4066(2) 0.0591(9) 1.000 . Uani d ? C(7Y) 0.4639(3) 0.2280(3) 0.3311(2) 0.0483(7) 1.000 . Uani d ? C(9Z) 0.6268(3) 0.2974(3) 0.4912(2) 0.065(1) 1.000 . Uani d ? C(11Z) 0.5595(4) 0.3109(4) 0.5904(2) 0.080(1) 1.000 . Uani d ? C(12Z) 0.4552(3) 0.0526(3) 0.1335(2) 0.0470(7) 1.000 . Uani d ? C(15Z) 0.1130(4) 0.1188(4) 0.4314(2) 0.087(1) 1.000 . Uani d ? H(19) 0.6271 0.3164 0.3257 0.064 1.000 . Uiso c ? H(20) 0.7358 0.0323 0.3910 0.076 1.000 . Uiso c ? H(21) 0.8137 0.1186 0.3044 0.076 1.000 . Uiso c ? H(22) 0.7560 -0.0012 0.2235 0.074 1.000 . Uiso c ? H(23) 0.6480 -0.0584 0.3095 0.074 1.000 . Uiso c ? H(24) 0.5787 0.2053 0.1980 0.057 1.000 . Uiso c ? H(25) 0.2324 0.0579 0.2672 0.060 1.000 . Uiso c ? H(26) 0.4233 0.0597 0.4296 0.071 1.000 . Uiso c ? H(27) 0.3101 0.2095 0.4546 0.071 1.000 . Uiso c ? H(28) 0.4066 0.3237 0.3126 0.058 1.000 . Uiso c ? H(29) 0.4546 0.3595 0.6009 0.096 1.000 . Uiso c ? H(30) 0.5750 0.2165 0.6244 0.096 1.000 . Uiso c ? H(31) 0.6059 0.3655 0.6091 0.096 1.000 . Uiso c ? H(32) 0.5933 0.0472 0.0152 0.082 1.000 . Uiso c ? H(33) 0.6418 0.0954 0.0809 0.082 1.000 . Uiso c ? H(34) 0.0482 0.1180 0.3973 0.104 1.000 . Uiso c ? H(35) 0.1268 0.0327 0.4740 0.104 1.000 . Uiso c ? H(36) 0.0695 0.2019 0.4634 0.104 1.000 . Uiso c ? O(20) 0.1378(7) 0.4515(7) 0.5284(5) 0.151(3) 0.500 . Uani 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(8) 0.080(1) 0.057(1) 0.097(2) -0.016(1) -0.042(1) -0.025(1) O(10) 0.127(2) 0.076(2) 0.237(4) 0.001(2) -0.124(3) -0.054(2) O(13) 0.049(1) 0.070(1) 0.080(1) -0.0223(9) -0.024(1) -0.024(1) N(6) 0.048(1) 0.056(1) 0.075(2) -0.010(1) -0.017(1) -0.016(1) N(14) 0.051(1) 0.061(1) 0.095(2) -0.012(1) -0.031(1) -0.033(1) C(1) 0.070(2) 0.049(2) 0.070(2) -0.021(1) -0.029(2) -0.012(1) C(2) 0.065(2) 0.065(2) 0.090(2) -0.032(2) -0.021(2) -0.016(2) C(3a) 0.051(1) 0.042(1) 0.052(2) -0.018(1) -0.018(1) -0.004(1) C(3) 0.050(2) 0.056(2) 0.066(2) -0.021(1) -0.016(1) -0.011(1) C(4) 0.044(1) 0.048(1) 0.050(1) -0.020(1) -0.014(1) -0.005(1) C(5) 0.049(2) 0.056(2) 0.053(2) -0.022(1) -0.013(1) -0.007(1) C(7a) 0.061(2) 0.058(2) 0.049(2) -0.025(1) -0.015(1) -0.010(1) C(7) 0.060(2) 0.057(2) 0.065(2) -0.016(1) -0.015(1) -0.021(1) C(9) 0.076(2) 0.063(2) 0.104(3) -0.015(2) -0.043(2) -0.028(2) C(11) 0.122(3) 0.072(2) 0.182(5) -0.010(2) -0.077(3) -0.057(3) C(12) 0.044(1) 0.054(1) 0.054(2) -0.022(1) -0.014(1) -0.010(1) C(15) 0.055(2) 0.076(2) 0.091(2) -0.002(2) -0.016(2) -0.025(2) O(8Z) 0.066(1) 0.092(1) 0.051(1) -0.039(1) -0.0146(9) -0.019(1) O(10Z) 0.101(2) 0.195(3) 0.085(2) -0.094(2) -0.014(2) -0.042(2) O(13Z) 0.047(1) 0.070(1) 0.070(1) -0.0234(9) -0.0210(9) -0.023(1) N(6Z) 0.046(1) 0.096(2) 0.054(1) -0.035(1) -0.008(1) -0.015(1) N(14Z) 0.053(1) 0.111(2) 0.062(2) -0.040(1) -0.010(1) -0.035(1) C(1Z) 0.055(2) 0.067(2) 0.048(2) -0.028(1) -0.014(1) -0.011(1) C(2Z) 0.054(2) 0.083(2) 0.063(2) -0.021(2) -0.025(1) -0.012(2) C(3Z) 0.050(2) 0.072(2) 0.071(2) -0.016(1) -0.021(1) -0.020(2) C(3Y) 0.043(1) 0.056(2) 0.050(1) -0.021(1) -0.014(1) -0.008(1) C(4Z) 0.041(1) 0.049(1) 0.051(2) -0.017(1) -0.016(1) -0.009(1) C(5Z) 0.047(2) 0.055(2) 0.058(2) -0.022(1) -0.021(1) -0.003(1) C(7Z) 0.054(2) 0.080(2) 0.052(2) -0.028(1) -0.012(1) -0.015(1) C(7Y) 0.048(1) 0.051(1) 0.051(2) -0.017(1) -0.017(1) -0.009(1) C(9Z) 0.061(2) 0.083(2) 0.065(2) -0.029(2) -0.020(2) -0.021(2) C(11Z) 0.090(2) 0.101(2) 0.065(2) -0.034(2) -0.027(2) -0.023(2) C(12Z) 0.040(1) 0.053(1) 0.055(2) -0.014(1) -0.016(1) -0.014(1) C(15Z) 0.061(2) 0.145(3) 0.067(2) -0.054(2) -0.005(2) -0.017(2) O(20) 0.132(5) 0.160(6) 0.185(7) -0.063(5) -0.013(5) -0.081(5) #--------------------------------------------------------------------------- #-- _refine_special_details ; H atoms at calculated positions, H atoms of water molecule not included. ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00010|Fo|^2^]' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method 'Zachariasen (1967)' _refine_ls_extinction_coef 0.0000075(5) _refine_ls_extinction_expression 'equ(3) Acta Cryst.(1968) A24, p213.' _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 3106 _refine_ls_number_parameters 317 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.0652 _refine_ls_R_factor_gt 0.0521 _refine_ls_wR_factor_all 0.0650 _refine_ls_wR_factor_ref 0.0634 _refine_ls_goodness_of_fit_all 2.664 _refine_ls_goodness_of_fit_ref 2.955 _refine_ls_shift/su_max 0.0045 _refine_ls_shift/su_mean 0.0009 _refine_diff_density_min -0.21 _refine_diff_density_max 0.27 #--------------------------------------------------------------------------- #-- _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(8) C(1) 1.449(3) . . yes O(8) C(9) 1.319(3) . . yes O(10) C(9) 1.184(3) . . yes O(13) C(12) 1.247(3) . . yes N(6) C(5) 1.348(3) . . yes N(6) C(7) 1.455(3) . . yes N(6) C(15) 1.449(3) . . yes N(14) C(12) 1.334(3) . . yes N(14) H(14) 0.85 . . no N(14) H(15) 0.85 . . no C(1) C(2) 1.510(4) . . yes C(1) C(7a) 1.525(3) . . yes C(1) H(1) 0.95 . . no C(2) C(3) 1.521(4) . . yes C(2) H(2) 0.95 . . no C(2) H(3) 0.95 . . no C(3a) C(3) 1.536(4) . . yes C(3a) C(4) 1.502(3) . . yes C(3a) C(7a) 1.530(3) . . yes C(3a) H(6) 0.95 . . no C(3) H(4) 0.95 . . no C(3) H(5) 0.95 . . no C(4) C(5) 1.352(3) . . yes C(4) C(12) 1.466(3) . . yes C(5) H(7) 0.95 . . no C(7a) C(7) 1.522(4) . . yes C(7a) H(10) 0.95 . . no C(7) H(8) 0.95 . . no C(7) H(9) 0.95 . . no C(9) C(11) 1.479(4) . . yes C(11) H(11) 0.95 . . no C(11) H(12) 0.95 . . no C(11) H(13) 0.95 . . no C(15) H(16) 0.95 . . no C(15) H(17) 0.95 . . no C(15) H(18) 0.95 . . no O(8Z) C(1Z) 1.464(3) . . yes O(8Z) C(9Z) 1.322(3) . . yes O(10Z) C(9Z) 1.194(4) . . yes O(13Z) C(12Z) 1.252(3) . . yes N(6Z) C(5Z) 1.336(3) . . yes N(6Z) C(7Z) 1.455(3) . . yes N(6Z) C(15Z) 1.428(4) . . yes N(14Z) C(12Z) 1.332(3) . . yes N(14Z) H(32) 0.85 . . no N(14Z) H(33) 0.85 . . no C(1Z) C(2Z) 1.510(4) . . yes C(1Z) C(7Y) 1.520(3) . . yes C(1Z) H(19) 0.95 . . no C(2Z) C(3Z) 1.533(4) . . yes C(2Z) H(20) 0.95 . . no C(2Z) H(21) 0.95 . . no C(3Z) C(3Y) 1.526(4) . . yes C(3Z) H(22) 0.95 . . no C(3Z) H(23) 0.95 . . no C(3Y) C(4Z) 1.508(3) . . yes C(3Y) C(7Y) 1.530(3) . . yes C(3Y) H(24) 0.95 . . no C(4Z) C(5Z) 1.352(3) . . yes C(4Z) C(12Z) 1.464(3) . . yes C(5Z) H(25) 0.95 . . no C(7Z) C(7Y) 1.527(4) . . yes C(7Z) H(26) 0.95 . . no C(7Z) H(27) 0.95 . . no C(7Y) H(28) 0.95 . . no C(9Z) C(11Z) 1.487(4) . . yes C(11Z) H(29) 0.95 . . no C(11Z) H(30) 0.95 . . no C(11Z) H(31) 0.95 . . no C(15Z) H(34) 0.95 . . no C(15Z) H(35) 0.95 . . no C(15Z) H(36) 0.95 . . no #--------------------------------------------------------------------------- #-- 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(8) C(9) 117.4(2) . . . yes C(5) N(6) C(7) 118.5(2) . . . yes C(5) N(6) C(15) 121.0(2) . . . yes C(7) N(6) C(15) 117.4(2) . . . yes C(12) N(14) H(14) 120.0 . . . no C(12) N(14) H(15) 120.0 . . . no H(14) N(14) H(15) 120.0 . . . no O(8) C(1) C(2) 112.1(2) . . . yes O(8) C(1) C(7a) 109.9(2) . . . yes O(8) C(1) H(1) 109.4 . . . no C(2) C(1) C(7a) 106.6(2) . . . yes C(2) C(1) H(1) 109.4 . . . no C(7a) C(1) H(1) 109.4 . . . no C(1) C(2) C(3) 105.8(2) . . . yes C(1) C(2) H(2) 110.4 . . . no C(1) C(2) H(3) 110.4 . . . no C(3) C(2) H(2) 110.4 . . . no C(3) C(2) H(3) 110.4 . . . no H(2) C(2) H(3) 109.5 . . . no C(3) C(3a) C(4) 115.6(2) . . . yes C(3) C(3a) C(7a) 103.8(2) . . . yes C(3) C(3a) H(6) 108.3 . . . no C(4) C(3a) C(7a) 112.2(2) . . . yes C(4) C(3a) H(6) 108.3 . . . no C(7a) C(3a) H(6) 108.3 . . . no C(2) C(3) C(3a) 106.7(2) . . . yes C(2) C(3) H(4) 110.2 . . . no C(2) C(3) H(5) 110.2 . . . no C(3a) C(3) H(4) 110.2 . . . no C(3a) C(3) H(5) 110.2 . . . no H(4) C(3) H(5) 109.5 . . . no C(3a) C(4) C(5) 120.0(2) . . . yes C(3a) C(4) C(12) 122.2(2) . . . yes C(5) C(4) C(12) 117.8(2) . . . yes N(6) C(5) C(4) 125.0(2) . . . yes N(6) C(5) H(7) 117.5 . . . no C(4) C(5) H(7) 117.5 . . . no C(1) C(7a) C(3a) 102.1(2) . . . yes C(1) C(7a) C(7) 113.3(2) . . . yes C(1) C(7a) H(10) 110.0 . . . no C(3a) C(7a) C(7) 111.1(2) . . . yes C(3a) C(7a) H(10) 110.0 . . . no C(7) C(7a) H(10) 110.0 . . . no N(6) C(7) C(7a) 110.6(2) . . . yes N(6) C(7) H(8) 109.2 . . . no N(6) C(7) H(9) 109.2 . . . no C(7a) C(7) H(8) 109.2 . . . no C(7a) C(7) H(9) 109.2 . . . no H(8) C(7) H(9) 109.5 . . . no O(8) C(9) O(10) 123.3(3) . . . yes O(8) C(9) C(11) 113.1(3) . . . yes O(10) C(9) C(11) 123.5(3) . . . yes C(9) C(11) H(11) 109.5 . . . no C(9) C(11) H(12) 109.5 . . . no C(9) C(11) H(13) 109.5 . . . no H(11) C(11) H(12) 109.5 . . . no H(11) C(11) H(13) 109.5 . . . no H(12) C(11) H(13) 109.5 . . . no O(13) C(12) N(14) 119.7(2) . . . yes O(13) C(12) C(4) 122.3(2) . . . yes N(14) C(12) C(4) 118.0(2) . . . yes N(6) C(15) H(16) 109.5 . . . no N(6) C(15) H(17) 109.5 . . . no N(6) C(15) H(18) 109.5 . . . no H(16) C(15) H(17) 109.5 . . . no H(16) C(15) H(18) 109.5 . . . no H(17) C(15) H(18) 109.5 . . . no C(1Z) O(8Z) C(9Z) 118.4(2) . . . yes C(5Z) N(6Z) C(7Z) 118.9(2) . . . yes C(5Z) N(6Z) C(15Z) 122.2(2) . . . yes C(7Z) N(6Z) C(15Z) 118.4(2) . . . yes C(12Z) N(14Z) H(32) 120.0 . . . no C(12Z) N(14Z) H(33) 120.0 . . . no H(32) N(14Z) H(33) 120.0 . . . no O(8Z) C(1Z) C(2Z) 113.0(2) . . . yes O(8Z) C(1Z) C(7Y) 108.2(2) . . . yes O(8Z) C(1Z) H(19) 109.4 . . . no C(2Z) C(1Z) C(7Y) 107.2(2) . . . yes C(2Z) C(1Z) H(19) 109.4 . . . no C(7Y) C(1Z) H(19) 109.5 . . . no C(1Z) C(2Z) C(3Z) 106.1(2) . . . yes C(1Z) C(2Z) H(20) 110.3 . . . no C(1Z) C(2Z) H(21) 110.3 . . . no C(3Z) C(2Z) H(20) 110.3 . . . no C(3Z) C(2Z) H(21) 110.3 . . . no H(20) C(2Z) H(21) 109.5 . . . no C(2Z) C(3Z) C(3Y) 105.5(2) . . . yes C(2Z) C(3Z) H(22) 110.5 . . . no C(2Z) C(3Z) H(23) 110.5 . . . no C(3Y) C(3Z) H(22) 110.5 . . . no C(3Y) C(3Z) H(23) 110.5 . . . no H(22) C(3Z) H(23) 109.5 . . . no C(3Z) C(3Y) C(4Z) 117.3(2) . . . yes C(3Z) C(3Y) C(7Y) 103.8(2) . . . yes C(3Z) C(3Y) H(24) 108.0 . . . no C(4Z) C(3Y) C(7Y) 111.3(2) . . . yes C(4Z) C(3Y) H(24) 108.0 . . . no C(7Y) C(3Y) H(24) 108.0 . . . no C(3Y) C(4Z) C(5Z) 119.4(2) . . . yes C(3Y) C(4Z) C(12Z) 123.6(2) . . . yes C(5Z) C(4Z) C(12Z) 116.7(2) . . . yes N(6Z) C(5Z) C(4Z) 125.8(2) . . . yes N(6Z) C(5Z) H(25) 117.1 . . . no C(4Z) C(5Z) H(25) 117.1 . . . no N(6Z) C(7Z) C(7Y) 110.2(2) . . . yes N(6Z) C(7Z) H(26) 109.3 . . . no N(6Z) C(7Z) H(27) 109.3 . . . no C(7Y) C(7Z) H(26) 109.3 . . . no C(7Y) C(7Z) H(27) 109.3 . . . no H(26) C(7Z) H(27) 109.5 . . . no C(1Z) C(7Y) C(3Y) 102.6(2) . . . yes C(1Z) C(7Y) C(7Z) 112.7(2) . . . yes C(1Z) C(7Y) H(28) 110.1 . . . no C(3Y) C(7Y) C(7Z) 110.9(2) . . . yes C(3Y) C(7Y) H(28) 110.1 . . . no C(7Z) C(7Y) H(28) 110.1 . . . no O(8Z) C(9Z) O(10Z) 122.7(3) . . . yes O(8Z) C(9Z) C(11Z) 111.9(3) . . . yes O(10Z) C(9Z) C(11Z) 125.3(3) . . . yes C(9Z) C(11Z) H(29) 109.5 . . . no C(9Z) C(11Z) H(30) 109.5 . . . no C(9Z) C(11Z) H(31) 109.5 . . . no H(29) C(11Z) H(30) 109.5 . . . no H(29) C(11Z) H(31) 109.5 . . . no H(30) C(11Z) H(31) 109.5 . . . no O(13Z) C(12Z) N(14Z) 119.6(2) . . . yes O(13Z) C(12Z) C(4Z) 122.1(2) . . . yes N(14Z) C(12Z) C(4Z) 118.2(2) . . . yes N(6Z) C(15Z) H(34) 109.5 . . . no N(6Z) C(15Z) H(35) 109.5 . . . no N(6Z) C(15Z) H(36) 109.5 . . . no H(34) C(15Z) H(35) 109.5 . . . no H(34) C(15Z) H(36) 109.5 . . . no H(35) C(15Z) H(36) 109.5 . . . no #--------------------------------------------------------------------------- #-- 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(8) O(20) 3.381(8) . . no O(10) C(7Y) 3.367(3) . 2_566 no O(10) O(20) 3.458(9) . 2_566 no O(10) C(11Z) 3.559(4) . 1_455 no O(13) N(14Z) 2.916(3) . 2_666 no O(13) N(14) 2.995(3) . 2_577 no N(6) C(3) 3.599(4) . 2_567 no N(14) O(13Z) 3.020(3) . 2_566 no N(14) N(14Z) 3.498(3) . 1_466 no C(3) C(5) 3.476(4) . 2_567 no C(3) O(13Z) 3.492(3) . 2_566 no C(9) O(20) 3.518(8) . . no C(15) O(13Z) 3.464(4) . 2_656 no O(10Z) O(20) 2.991(6) . 2_666 no O(10Z) C(15Z) 3.485(4) . 1_655 no O(13Z) N(14Z) 2.941(3) . 2_655 no C(7Z) O(20) 3.541(7) . . no O(20) O(20) 2.89(1) . 2_566 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O(8) C(1) C(2) C(3) . . . . 140.3(2) no O(8) C(1) C(7a) C(3a) . . . . -157.8(2) no O(8) C(1) C(7a) C(7) . . . . -38.2(3) no O(10) C(9) O(8) C(1) . . . . 2.8(5) no O(13) C(12) C(4) C(3a) . . . . 178.8(2) no O(13) C(12) C(4) C(5) . . . . -1.0(4) no N(6) C(5) C(4) C(3a) . . . . -1.5(4) no N(6) C(5) C(4) C(12) . . . . 178.3(2) no N(6) C(7) C(7a) C(1) . . . . -168.8(2) no N(6) C(7) C(7a) C(3a) . . . . -54.5(3) no N(14) C(12) C(4) C(3a) . . . . -0.9(4) no N(14) C(12) C(4) C(5) . . . . 179.3(2) no C(1) O(8) C(9) C(11) . . . . -175.2(3) no C(1) C(2) C(3) C(3a) . . . . 4.1(3) no C(1) C(7a) C(3a) C(3) . . . . 37.8(2) no C(1) C(7a) C(3a) C(4) . . . . 163.3(2) no C(2) C(1) O(8) C(9) . . . . 80.7(3) no C(2) C(1) C(7a) C(3a) . . . . -36.1(3) no C(2) C(1) C(7a) C(7) . . . . 83.5(3) no C(2) C(3) C(3a) C(4) . . . . -149.7(2) no C(2) C(3) C(3a) C(7a) . . . . -26.3(3) no C(3) C(2) C(1) C(7a) . . . . 20.0(3) no C(3) C(3a) C(4) C(5) . . . . 103.9(3) no C(3) C(3a) C(4) C(12) . . . . -75.9(3) no C(3) C(3a) C(7a) C(7) . . . . -83.4(2) no C(4) C(3a) C(7a) C(7) . . . . 42.2(3) no C(4) C(5) N(6) C(7) . . . . -11.8(4) no C(4) C(5) N(6) C(15) . . . . -171.1(3) no C(5) N(6) C(7) C(7a) . . . . 39.8(3) no C(5) C(4) C(3a) C(7a) . . . . -14.9(3) no C(7a) C(1) O(8) C(9) . . . . -161.0(3) no C(7a) C(3a) C(4) C(12) . . . . 165.3(2) no C(7a) C(7) N(6) C(15) . . . . -160.1(2) no O(8Z) C(1Z) C(2Z) C(3Z) . . . . 131.1(2) no O(8Z) C(1Z) C(7Y) C(3Y) . . . . -153.6(2) no O(8Z) C(1Z) C(7Y) C(7Z) . . . . -34.3(3) no O(10Z) C(9Z) O(8Z) C(1Z) . . . . -2.1(5) no O(13Z) C(12Z) C(4Z) C(3Y) . . . . -179.7(2) no O(13Z) C(12Z) C(4Z) C(5Z) . . . . -4.9(4) no N(6Z) C(5Z) C(4Z) C(3Y) . . . . -2.1(4) no N(6Z) C(5Z) C(4Z) C(12Z) . . . . -177.2(2) no N(6Z) C(7Z) C(7Y) C(1Z) . . . . -169.7(2) no N(6Z) C(7Z) C(7Y) C(3Y) . . . . -55.3(3) no N(14Z) C(12Z) C(4Z) C(3Y) . . . . -0.9(4) no N(14Z) C(12Z) C(4Z) C(5Z) . . . . 173.9(2) no C(1Z) O(8Z) C(9Z) C(11Z) . . . . 178.1(2) no C(1Z) C(2Z) C(3Z) C(3Y) . . . . 12.4(3) no C(1Z) C(7Y) C(3Y) C(3Z) . . . . 38.6(2) no C(1Z) C(7Y) C(3Y) C(4Z) . . . . 165.7(2) no C(2Z) C(1Z) O(8Z) C(9Z) . . . . 80.3(3) no C(2Z) C(1Z) C(7Y) C(3Y) . . . . -31.4(3) no C(2Z) C(1Z) C(7Y) C(7Z) . . . . 87.9(3) no C(2Z) C(3Z) C(3Y) C(4Z) . . . . -155.0(2) no C(2Z) C(3Z) C(3Y) C(7Y) . . . . -31.7(3) no C(3Z) C(2Z) C(1Z) C(7Y) . . . . 12.0(3) no C(3Z) C(3Y) C(4Z) C(5Z) . . . . 102.1(3) no C(3Z) C(3Y) C(4Z) C(12Z) . . . . -83.2(3) no C(3Z) C(3Y) C(7Y) C(7Z) . . . . -82.0(2) no C(4Z) C(3Y) C(7Y) C(7Z) . . . . 45.1(3) no C(4Z) C(5Z) N(6Z) C(7Z) . . . . -8.8(4) no C(4Z) C(5Z) N(6Z) C(15Z) . . . . -180.0(3) no C(5Z) N(6Z) C(7Z) C(7Y) . . . . 37.6(3) no C(5Z) C(4Z) C(3Y) C(7Y) . . . . -17.2(3) no C(7Y) C(1Z) O(8Z) C(9Z) . . . . -161.2(2) no C(7Y) C(3Y) C(4Z) C(12Z) . . . . 157.5(2) no C(7Y) C(7Z) N(6Z) C(15Z) . . . . -151.0(3) no #--------------------------------------------------------------------------- #-- loop_ _geom_bond_atom_site_label_D _geom_bond_atom_site_label_H _geom_contact_atom_site_label_A _geom_bond_distance_DH _geom_contact_distance_HA _geom_contact_distance_DA _geom_angle_DHA _geom_contact_site_symmetry_A 'N(14)' 'H(15)' 'O(13)' '0.85' '2.16' '2.232(3)' '166.7' '2_755' 'N(14Z)' 'H(32)' 'O(13Z)' '0.85' '2.09' '2.941(3)' '177.3' '2_677' 'N(14Z)' 'H(33)' 'O(13)' '0.85' '2.14' '2.916(3)' '152.2' '2_666' #--------------------------------------------------------------------------- #-- #===END