# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _audit_creation_date 2007-06-22 _audit_creation_method 'by CrystalStructure 3.8' _audit_update_record ? _publ_contact_author_name 'Takeshi Imanishi' _publ_contact_author_address ; Graduate School of Pharmaceutical Sciences Osaka University 1-6 Yamadaoka Osaka 565-0871 Suita Osaka 565-0871 JAPAN ; _publ_contact_author_email imanishi@phs.osaka-u.ac.jp _publ_contact_author_fax +81-6-6879-8204 _publ_contact_author_phone +81-6-6879-8200 _publ_section_title ; N-Methyl substituted 2',4'-BNANC: a highly nuclease-resistant nucleic acid analogue with high-affinity RNA selective hybridization ; #============================================================================== _publ_section_references ; Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., Giacovazzo, C., Guagliardi, A., Moliterni, A.G.G., Polidori, G. & Spagna, R. (1999). SIR97. A New Tool for Crystal Structure Determination and Refinement. J. App. Cryst., 32, 115-119. Johnson, C.K. (1976). ORTEP-II. A FORTRAN Thermal-Ellipsoid Plot Program. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA. Rigaku (1998). PROCESS-AUTO. Automatic Data Acquisition and Processing Package for Imaging Plate Diffractometer. Rigaku Corporation, Tokyo 196-8666, Japan Rigaku & RAC (2007). CrystalStructure (Version 3.80). Single Crystal Structure Analysis Software. Rigaku, Tokyo 196-8666, Japan. Rigaku Americas, TX, USA 77381-5209. Sheldrick, G.M. (1997). SHELXL97. University of Gottingen, Germany. ; loop_ _publ_author_name 'Takeshi Imanishi' 'Kazuyuki Miyashita' 'Satoshi Obika' 'S. M. Abdur Rahman' 'Sayori Seki' #============================================================================== data__YKS-406 _database_code_depnum_ccdc_archive 'CCDC 647092' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C12 H17 N3 O6 ' _chemical_formula_moiety 'C12 H17 N3 O6 ' _chemical_formula_weight 299.28 _chemical_melting_point ? _chemical_absolute_configuration rm #============================================================================== # CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 1/2+X,1/2-Y,-Z 3 -X,1/2+Y,1/2-Z 4 1/2-X,-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 8.721(4) _cell_length_b 10.414(4) _cell_length_c 13.992(5) _cell_angle_alpha 90.0000 _cell_angle_beta 90.0000 _cell_angle_gamma 90.0000 _cell_volume 1270.8(9) _cell_formula_units_Z 4 _cell_measurement_reflns_used 13430 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 30.1 _cell_measurement_temperature 93.1 #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.564 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632.00 _exptl_absorpt_coefficient_mu 0.126 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_absorpt_correction_T_min 0.920 _exptl_absorpt_correction_T_max 0.987 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_reflns_number 15243 _diffrn_reflns_av_R_equivalents 0.040 _diffrn_reflns_theta_max 30.03 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. 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 2126 _reflns_number_gt 1869 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0291 _refine_ls_wR_factor_ref 0.0699 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 2126 _refine_ls_number_parameters 193 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0441P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.0010 _refine_diff_density_max 0.28 _refine_diff_density_min -0.22 _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 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.006 0.003 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.011 0.006 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O(1) O -0.10154(12) 0.48924(10) 0.58259(7) 0.0114(2) Uani 1.00 1 d . . . O(2) O 0.09994(14) 0.69417(10) 0.60287(8) 0.0141(2) Uani 1.00 1 d . . . O(3) O 0.33726(14) 0.54972(11) 0.34641(7) 0.0172(2) Uani 1.00 1 d . . . O(4) O 0.20556(13) 0.39201(10) 0.49795(7) 0.0112(2) Uani 1.00 1 d . . . O(5) O 0.01613(13) 0.18533(10) 0.71176(7) 0.0132(2) Uani 1.00 1 d . . . O(6) O 0.48121(13) 0.11321(12) 0.84726(8) 0.0184(2) Uani 1.00 1 d . . . N(1) N -0.09429(15) 0.47094(12) 0.47776(8) 0.0114(2) Uani 1.00 1 d . . . N(2) N 0.22454(15) 0.28197(12) 0.64535(8) 0.0099(2) Uani 1.00 1 d . . . N(3) N 0.25129(15) 0.15307(12) 0.77850(9) 0.0119(2) Uani 1.00 1 d . . . C(1) C 0.11936(18) 0.34521(14) 0.57617(9) 0.0103(2) Uani 1.00 1 d . . . C(2) C 0.04410(17) 0.46215(14) 0.62303(10) 0.0103(2) Uani 1.00 1 d . . . C(3) C 0.15736(18) 0.56809(14) 0.59498(10) 0.0103(2) Uani 1.00 1 d . . . C(4) C 0.17810(17) 0.53026(14) 0.49029(10) 0.0104(2) Uani 1.00 1 d . . . C(5) C 0.31505(18) 0.59063(15) 0.44254(10) 0.0139(3) Uani 1.00 1 d . . . C(6) C 0.02742(18) 0.55404(15) 0.43761(11) 0.0124(3) Uani 1.00 1 d . . . C(7) C -0.24583(19) 0.51389(16) 0.44775(11) 0.0149(3) Uani 1.00 1 d . . . C(8) C 0.15589(18) 0.20621(14) 0.71231(11) 0.0107(2) Uani 1.00 1 d . . . C(9) C 0.40980(19) 0.16899(14) 0.78431(10) 0.0119(2) Uani 1.00 1 d . . . C(10) C 0.47434(18) 0.25286(15) 0.71255(11) 0.0121(3) Uani 1.00 1 d . . . C(11) C 0.38023(18) 0.30541(15) 0.64755(11) 0.0116(2) Uani 1.00 1 d . . . C(12) C 0.64429(18) 0.27553(16) 0.71254(11) 0.0160(3) Uani 1.00 1 d . . . H(1) H 0.0395 0.2833 0.5537 0.012 Uiso 1.00 1 c R . . H(2) H 0.0376 0.4521 0.6940 0.012 Uiso 1.00 1 c R . . H(3) H 0.2559 0.5588 0.6309 0.012 Uiso 1.00 1 c R . . H(4) H 0.3025 0.6851 0.4433 0.017 Uiso 1.00 1 c R . . H(5) H 0.4080 0.5696 0.4800 0.017 Uiso 1.00 1 c R . . H(6) H -0.0025 0.6453 0.4442 0.015 Uiso 1.00 1 c R . . H(7) H 0.0407 0.5352 0.3688 0.015 Uiso 1.00 1 c R . . H(8) H -0.2552 0.5051 0.3783 0.018 Uiso 1.00 1 c R . . H(9) H -0.2599 0.6041 0.4657 0.018 Uiso 1.00 1 c R . . H(10) H -0.3243 0.4613 0.4791 0.018 Uiso 1.00 1 c R . . H(11) H 0.2085 0.1037 0.8220 0.014 Uiso 1.00 1 c R . . H(12) H 0.4227 0.3613 0.6009 0.014 Uiso 1.00 1 c R . . H(13) H 0.6701 0.3391 0.6634 0.019 Uiso 1.00 1 c R . . H(14) H 0.6976 0.1948 0.6988 0.019 Uiso 1.00 1 c R . . H(15) H 0.6761 0.3076 0.7753 0.019 Uiso 1.00 1 c R . . H(16) H 0.0700 0.7071 0.6591 0.017 Uiso 1.00 1 c R . . H(17) H 0.3895 0.4819 0.3459 0.021 Uiso 1.00 1 c 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.0103(5) 0.0159(5) 0.0078(4) 0.0015(4) 0.0003(4) -0.0006(3) O(2) 0.0186(5) 0.0108(5) 0.0128(4) 0.0009(4) 0.0015(4) -0.0010(4) O(3) 0.0205(6) 0.0196(5) 0.0116(4) 0.0014(5) 0.0042(4) 0.0002(4) O(4) 0.0144(5) 0.0103(4) 0.0089(4) 0.0022(4) 0.0028(4) 0.0013(3) O(5) 0.0098(5) 0.0167(5) 0.0132(5) -0.0010(4) -0.0000(4) 0.0016(4) O(6) 0.0158(5) 0.0229(5) 0.0165(5) 0.0015(5) -0.0040(4) 0.0053(4) N(1) 0.0117(6) 0.0153(6) 0.0071(5) -0.0006(5) -0.0007(4) -0.0007(5) N(2) 0.0092(5) 0.0115(5) 0.0091(5) -0.0001(4) -0.0012(5) 0.0024(4) N(3) 0.0113(6) 0.0139(5) 0.0106(5) -0.0015(4) 0.0004(5) 0.0045(4) C(1) 0.0110(7) 0.0124(6) 0.0077(6) 0.0018(5) -0.0006(5) 0.0018(5) C(2) 0.0100(6) 0.0118(6) 0.0090(6) 0.0002(5) -0.0010(5) 0.0006(5) C(3) 0.0106(6) 0.0103(6) 0.0099(6) -0.0007(5) 0.0009(5) -0.0003(5) C(4) 0.0120(7) 0.0096(6) 0.0096(6) 0.0003(5) 0.0003(5) 0.0010(5) C(5) 0.0151(7) 0.0161(7) 0.0104(6) -0.0016(6) 0.0024(6) 0.0002(5) C(6) 0.0155(7) 0.0127(6) 0.0091(6) 0.0000(6) -0.0005(5) 0.0010(5) C(7) 0.0149(7) 0.0165(7) 0.0135(6) 0.0008(6) -0.0047(6) -0.0007(5) C(8) 0.0127(7) 0.0092(6) 0.0102(6) 0.0007(5) 0.0009(5) -0.0014(5) C(9) 0.0124(7) 0.0122(6) 0.0111(6) 0.0020(5) -0.0006(6) -0.0023(5) C(10) 0.0109(7) 0.0133(6) 0.0121(6) 0.0005(5) 0.0014(6) -0.0022(5) C(11) 0.0104(7) 0.0126(6) 0.0118(6) -0.0007(5) 0.0015(5) 0.0002(5) C(12) 0.0114(7) 0.0205(7) 0.0160(7) -0.0001(6) 0.0009(6) 0.0008(6) #============================================================================== _computing_data_collection 'PROCESS-AUTO (Rigaku, 1998)' _computing_cell_refinement 'PROCESS-AUTO (Rigaku, 1998)' _computing_data_reduction 'CrystalStructure (Rigaku & RAC 2007)' _computing_structure_solution 'SIR97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_publication_material 'CrystalStructure (Rigaku & RAC 2007)' _computing_molecular_graphics 'ORTEP (Johnson, 1976)' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 O(1) N(1) 1.4805(14) yes . . O(1) C(2) 1.4188(17) yes . . O(2) C(3) 1.4096(18) yes . . O(3) C(5) 1.4242(17) yes . . O(4) C(1) 1.4144(17) yes . . O(4) C(4) 1.4634(17) yes . . O(5) C(8) 1.2381(19) yes . . O(6) C(9) 1.2252(18) yes . . N(1) C(6) 1.480(2) yes . . N(1) C(7) 1.457(2) yes . . N(2) C(1) 1.4873(18) yes . . N(2) C(8) 1.3633(19) yes . . N(2) C(11) 1.380(2) yes . . N(3) C(8) 1.3624(19) yes . . N(3) C(9) 1.395(2) yes . . C(1) C(2) 1.531(2) yes . . C(2) C(3) 1.532(2) yes . . C(3) C(4) 1.5276(19) yes . . C(4) C(5) 1.506(2) yes . . C(4) C(6) 1.527(2) yes . . C(9) C(10) 1.445(2) yes . . C(10) C(11) 1.342(2) yes . . C(10) C(12) 1.501(2) yes . . O(2) H(16) 0.840 no . . O(3) H(17) 0.840 no . . N(3) H(11) 0.880 no . . C(1) H(1) 1.000 no . . C(2) H(2) 1.000 no . . C(3) H(3) 1.000 no . . C(5) H(4) 0.990 no . . C(5) H(5) 0.990 no . . C(6) H(6) 0.990 no . . C(6) H(7) 0.990 no . . C(7) H(8) 0.980 no . . C(7) H(9) 0.980 no . . C(7) H(10) 0.980 no . . C(11) H(12) 0.950 no . . C(12) H(13) 0.980 no . . C(12) H(14) 0.980 no . . C(12) H(15) 0.980 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 N(1) O(1) C(2) 109.35(10) yes . . . C(1) O(4) C(4) 107.98(10) yes . . . O(1) N(1) C(6) 109.35(10) yes . . . O(1) N(1) C(7) 101.96(10) yes . . . C(6) N(1) C(7) 111.20(11) yes . . . C(1) N(2) C(8) 115.64(12) yes . . . C(1) N(2) C(11) 122.89(12) yes . . . C(8) N(2) C(11) 121.28(12) yes . . . C(8) N(3) C(9) 126.63(12) yes . . . O(4) C(1) N(2) 109.17(12) yes . . . O(4) C(1) C(2) 106.57(11) yes . . . N(2) C(1) C(2) 109.75(10) yes . . . O(1) C(2) C(1) 111.79(11) yes . . . O(1) C(2) C(3) 109.38(11) yes . . . C(1) C(2) C(3) 100.76(11) yes . . . O(2) C(3) C(2) 114.94(12) yes . . . O(2) C(3) C(4) 110.94(11) yes . . . C(2) C(3) C(4) 97.83(11) yes . . . O(4) C(4) C(3) 101.70(10) yes . . . O(4) C(4) C(5) 108.26(11) yes . . . O(4) C(4) C(6) 109.62(11) yes . . . C(3) C(4) C(5) 114.31(12) yes . . . C(3) C(4) C(6) 108.61(12) yes . . . C(5) C(4) C(6) 113.62(12) yes . . . O(3) C(5) C(4) 113.70(12) yes . . . N(1) C(6) C(4) 109.82(12) yes . . . O(5) C(8) N(2) 121.98(13) yes . . . O(5) C(8) N(3) 122.28(13) yes . . . N(2) C(8) N(3) 115.72(13) yes . . . O(6) C(9) N(3) 119.30(13) yes . . . O(6) C(9) C(10) 126.03(15) yes . . . N(3) C(9) C(10) 114.67(12) yes . . . C(9) C(10) C(11) 118.64(14) yes . . . C(9) C(10) C(12) 118.68(13) yes . . . C(11) C(10) C(12) 122.67(14) yes . . . N(2) C(11) C(10) 123.02(14) yes . . . C(3) O(2) H(16) 109.5 no . . . C(5) O(3) H(17) 109.5 no . . . C(8) N(3) H(11) 116.7 no . . . C(9) N(3) H(11) 116.7 no . . . O(4) C(1) H(1) 110.4 no . . . N(2) C(1) H(1) 110.4 no . . . C(2) C(1) H(1) 110.4 no . . . O(1) C(2) H(2) 111.5 no . . . C(1) C(2) H(2) 111.5 no . . . C(3) C(2) H(2) 111.5 no . . . O(2) C(3) H(3) 110.8 no . . . C(2) C(3) H(3) 110.8 no . . . C(4) C(3) H(3) 110.8 no . . . O(3) C(5) H(4) 108.8 no . . . O(3) C(5) H(5) 108.8 no . . . C(4) C(5) H(4) 108.8 no . . . C(4) C(5) H(5) 108.8 no . . . H(4) C(5) H(5) 107.7 no . . . N(1) C(6) H(6) 109.7 no . . . N(1) C(6) H(7) 109.7 no . . . C(4) C(6) H(6) 109.7 no . . . C(4) C(6) H(7) 109.7 no . . . H(6) C(6) H(7) 108.2 no . . . N(1) C(7) H(8) 109.5 no . . . N(1) C(7) H(9) 109.5 no . . . N(1) C(7) H(10) 109.5 no . . . H(8) C(7) H(9) 109.5 no . . . H(8) C(7) H(10) 109.5 no . . . H(9) C(7) H(10) 109.5 no . . . N(2) C(11) H(12) 118.5 no . . . C(10) C(11) H(12) 118.5 no . . . C(10) C(12) H(13) 109.5 no . . . C(10) C(12) H(14) 109.5 no . . . C(10) C(12) H(15) 109.5 no . . . H(13) C(12) H(14) 109.5 no . . . H(13) C(12) H(15) 109.5 no . . . H(14) C(12) H(15) 109.5 no . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 O(1) N(3) 2.8973(16) ? . 3_556 O(2) O(3) 3.5868(16) ? . 2_466 O(2) O(5) 2.7858(15) ? . 3_556 O(2) N(3) 3.5102(17) ? . 3_556 O(2) C(5) 3.4058(19) ? . 2_466 O(2) C(7) 3.3991(19) ? . 2_566 O(2) C(8) 3.4178(19) ? . 3_556 O(2) C(12) 3.5163(19) ? . 3_656 O(3) O(2) 3.5868(16) ? . 2_566 O(3) O(5) 3.0146(15) ? . 2_556 O(3) O(5) 3.5773(15) ? . 4_564 O(3) N(2) 3.3581(15) ? . 4_564 O(3) N(3) 3.3285(16) ? . 4_564 O(3) C(2) 3.2947(17) ? . 4_564 O(3) C(8) 3.1598(18) ? . 4_564 O(4) C(12) 3.4647(18) ? . 2_456 O(5) O(2) 2.7858(15) ? . 3_546 O(5) O(3) 3.0146(15) ? . 2_456 O(5) O(3) 3.5773(15) ? . 4_565 O(5) C(2) 3.3198(17) ? . 3_546 O(5) C(3) 3.3305(17) ? . 3_546 O(5) C(12) 3.3762(19) ? . 1_455 O(6) C(3) 3.2878(19) ? . 3_646 O(6) C(5) 3.4442(18) ? . 3_646 O(6) C(11) 3.4264(19) ? . 3_646 N(1) N(2) 3.5214(17) ? . 2_456 N(1) C(10) 3.5890(19) ? . 2_456 N(1) C(11) 3.3773(19) ? . 2_456 N(2) O(3) 3.3581(15) ? . 4_565 N(2) N(1) 3.5214(17) ? . 2_556 N(2) C(7) 3.355(2) ? . 2_556 N(3) O(1) 2.8973(16) ? . 3_546 N(3) O(2) 3.5102(17) ? . 3_546 N(3) O(3) 3.3285(16) ? . 4_565 N(3) C(2) 3.5338(19) ? . 3_546 N(3) C(5) 3.5675(19) ? . 4_565 C(2) O(3) 3.2947(17) ? . 4_565 C(2) O(5) 3.3198(17) ? . 3_556 C(2) N(3) 3.5338(19) ? . 3_556 C(3) O(5) 3.3305(17) ? . 3_556 C(3) O(6) 3.2878(19) ? . 3_656 C(5) O(2) 3.4058(19) ? . 2_566 C(5) O(6) 3.4442(18) ? . 3_656 C(5) N(3) 3.5675(19) ? . 4_564 C(7) O(2) 3.3991(19) ? . 2_466 C(7) N(2) 3.355(2) ? . 2_456 C(7) C(8) 3.317(2) ? . 2_456 C(8) O(2) 3.4178(19) ? . 3_546 C(8) O(3) 3.1598(18) ? . 4_565 C(8) C(7) 3.317(2) ? . 2_556 C(10) N(1) 3.5890(19) ? . 2_556 C(11) O(6) 3.4264(19) ? . 3_656 C(11) N(1) 3.3773(19) ? . 2_556 C(12) O(2) 3.5163(19) ? . 3_646 C(12) O(4) 3.4647(18) ? . 2_556 C(12) O(5) 3.3762(19) ? . 1_655 O(1) H(4) 3.512 ? . 2_466 O(1) H(11) 2.018 ? . 3_556 O(1) H(13) 2.773 ? . 1_455 O(2) H(4) 2.954 ? . 2_466 O(2) H(5) 3.193 ? . 2_466 O(2) H(8) 3.387 ? . 2_566 O(2) H(9) 2.614 ? . 2_566 O(2) H(11) 3.038 ? . 3_556 O(2) H(14) 3.289 ? . 3_656 O(2) H(15) 2.848 ? . 3_656 O(3) H(2) 2.396 ? . 4_564 O(3) H(3) 3.321 ? . 4_564 O(3) H(14) 2.892 ? . 2_456 O(3) H(16) 3.246 ? . 2_566 O(4) H(1) 3.512 ? . 2_556 O(4) H(13) 3.315 ? . 2_456 O(4) H(14) 2.899 ? . 2_456 O(5) H(2) 2.803 ? . 3_546 O(5) H(3) 3.494 ? . 3_546 O(5) H(8) 3.082 ? . 2_556 O(5) H(10) 3.376 ? . 2_556 O(5) H(13) 3.482 ? . 1_455 O(5) H(14) 2.786 ? . 1_455 O(5) H(15) 3.347 ? . 1_455 O(5) H(16) 1.970 ? . 3_546 O(5) H(17) 2.215 ? . 2_456 O(6) H(3) 2.382 ? . 3_646 O(6) H(4) 3.564 ? . 3_646 O(6) H(4) 3.513 ? . 4_565 O(6) H(5) 2.642 ? . 3_646 O(6) H(6) 2.863 ? . 4_565 O(6) H(7) 3.434 ? . 2_556 O(6) H(9) 3.253 ? . 3_546 O(6) H(10) 3.206 ? . 3_546 O(6) H(12) 2.848 ? . 3_646 O(6) H(13) 3.149 ? . 3_646 N(1) H(11) 3.279 ? . 3_556 N(1) H(13) 3.586 ? . 1_455 N(2) H(8) 3.013 ? . 2_556 N(2) H(10) 3.104 ? . 2_556 N(3) H(2) 3.298 ? . 3_546 N(3) H(4) 2.894 ? . 4_565 N(3) H(8) 2.744 ? . 2_556 N(3) H(13) 3.438 ? . 3_646 N(3) H(16) 2.988 ? . 3_546 C(1) H(10) 3.321 ? . 2_556 C(2) H(11) 2.760 ? . 3_556 C(2) H(13) 3.550 ? . 1_455 C(2) H(17) 3.225 ? . 4_565 C(3) H(9) 3.591 ? . 2_566 C(3) H(11) 3.416 ? . 3_556 C(3) H(14) 3.415 ? . 3_656 C(3) H(15) 3.409 ? . 3_656 C(3) H(17) 3.572 ? . 4_565 C(4) H(14) 3.539 ? . 2_456 C(5) H(6) 3.550 ? . 2_566 C(5) H(9) 3.490 ? . 2_566 C(5) H(10) 3.459 ? . 1_655 C(5) H(16) 3.377 ? . 2_566 C(6) H(14) 3.544 ? . 2_456 C(6) H(15) 3.222 ? . 4_564 C(7) H(4) 3.511 ? . 2_466 C(7) H(5) 3.107 ? . 1_455 C(7) H(11) 3.370 ? . 3_556 C(7) H(15) 3.106 ? . 4_564 C(7) H(17) 3.501 ? . 1_455 C(8) H(2) 3.401 ? . 3_546 C(8) H(4) 3.444 ? . 4_565 C(8) H(8) 2.655 ? . 2_556 C(8) H(10) 3.201 ? . 2_556 C(8) H(16) 2.668 ? . 3_546 C(8) H(17) 3.147 ? . 2_456 C(9) H(3) 3.350 ? . 3_646 C(9) H(4) 3.269 ? . 4_565 C(9) H(6) 3.066 ? . 4_565 C(9) H(7) 3.227 ? . 2_556 C(9) H(7) 3.328 ? . 4_565 C(9) H(8) 3.246 ? . 2_556 C(9) H(13) 3.581 ? . 3_646 C(10) H(6) 3.420 ? . 4_565 C(10) H(7) 3.260 ? . 2_556 C(10) H(7) 3.109 ? . 4_565 C(10) H(8) 3.584 ? . 2_556 C(11) H(1) 3.273 ? . 2_556 C(11) H(7) 3.579 ? . 4_565 C(11) H(8) 3.462 ? . 2_556 C(12) H(3) 3.263 ? . 3_646 C(12) H(6) 3.566 ? . 4_565 C(12) H(7) 3.547 ? . 2_556 C(12) H(7) 3.356 ? . 4_565 C(12) H(8) 3.396 ? . 4_565 C(12) H(16) 3.153 ? . 3_646 C(12) H(17) 3.525 ? . 2_556 H(1) O(4) 3.512 ? . 2_456 H(1) C(11) 3.273 ? . 2_456 H(1) H(10) 2.848 ? . 2_556 H(1) H(12) 2.826 ? . 2_456 H(1) H(13) 3.486 ? . 2_456 H(1) H(17) 3.364 ? . 2_456 H(2) O(3) 2.396 ? . 4_565 H(2) O(5) 2.803 ? . 3_556 H(2) N(3) 3.298 ? . 3_556 H(2) C(8) 3.401 ? . 3_556 H(2) H(8) 3.593 ? . 4_465 H(2) H(11) 2.674 ? . 3_556 H(2) H(13) 3.441 ? . 1_455 H(2) H(16) 3.408 ? . 3_546 H(2) H(17) 2.322 ? . 4_565 H(3) O(3) 3.321 ? . 4_565 H(3) O(5) 3.494 ? . 3_556 H(3) O(6) 2.382 ? . 3_656 H(3) C(9) 3.350 ? . 3_656 H(3) C(12) 3.263 ? . 3_656 H(3) H(14) 2.801 ? . 3_656 H(3) H(15) 2.963 ? . 3_656 H(3) H(17) 3.291 ? . 4_565 H(4) O(1) 3.512 ? . 2_566 H(4) O(2) 2.954 ? . 2_566 H(4) O(6) 3.564 ? . 3_656 H(4) O(6) 3.513 ? . 4_564 H(4) N(3) 2.894 ? . 4_564 H(4) C(7) 3.511 ? . 2_566 H(4) C(8) 3.444 ? . 4_564 H(4) C(9) 3.269 ? . 4_564 H(4) H(6) 2.913 ? . 2_566 H(4) H(9) 2.595 ? . 2_566 H(4) H(11) 2.780 ? . 4_564 H(4) H(16) 2.959 ? . 2_566 H(5) O(2) 3.193 ? . 2_566 H(5) O(6) 2.642 ? . 3_656 H(5) C(7) 3.107 ? . 1_655 H(5) H(6) 3.247 ? . 2_566 H(5) H(8) 3.332 ? . 1_655 H(5) H(9) 2.925 ? . 1_655 H(5) H(10) 2.592 ? . 1_655 H(5) H(16) 3.345 ? . 2_566 H(6) O(6) 2.863 ? . 4_564 H(6) C(5) 3.550 ? . 2_466 H(6) C(9) 3.066 ? . 4_564 H(6) C(10) 3.420 ? . 4_564 H(6) C(12) 3.566 ? . 4_564 H(6) H(4) 2.913 ? . 2_466 H(6) H(5) 3.247 ? . 2_466 H(6) H(9) 3.588 ? . 2_566 H(6) H(15) 2.850 ? . 4_564 H(7) O(6) 3.434 ? . 2_456 H(7) C(9) 3.227 ? . 2_456 H(7) C(9) 3.328 ? . 4_564 H(7) C(10) 3.260 ? . 2_456 H(7) C(10) 3.109 ? . 4_564 H(7) C(11) 3.579 ? . 4_564 H(7) C(12) 3.547 ? . 2_456 H(7) C(12) 3.356 ? . 4_564 H(7) H(14) 2.916 ? . 2_456 H(7) H(15) 2.822 ? . 4_564 H(8) O(2) 3.387 ? . 2_466 H(8) O(5) 3.082 ? . 2_456 H(8) N(2) 3.013 ? . 2_456 H(8) N(3) 2.744 ? . 2_456 H(8) C(8) 2.655 ? . 2_456 H(8) C(9) 3.246 ? . 2_456 H(8) C(10) 3.584 ? . 2_456 H(8) C(11) 3.462 ? . 2_456 H(8) C(12) 3.396 ? . 4_564 H(8) H(2) 3.593 ? . 4_464 H(8) H(5) 3.332 ? . 1_455 H(8) H(11) 3.039 ? . 2_456 H(8) H(13) 3.495 ? . 4_564 H(8) H(15) 2.521 ? . 4_564 H(8) H(16) 3.402 ? . 2_466 H(8) H(17) 3.141 ? . 1_455 H(9) O(2) 2.614 ? . 2_466 H(9) O(6) 3.253 ? . 3_556 H(9) C(3) 3.591 ? . 2_466 H(9) C(5) 3.490 ? . 2_466 H(9) H(4) 2.595 ? . 2_466 H(9) H(5) 2.925 ? . 1_455 H(9) H(6) 3.588 ? . 2_466 H(9) H(11) 3.003 ? . 3_556 H(9) H(15) 2.911 ? . 4_564 H(9) H(16) 3.020 ? . 2_466 H(10) O(5) 3.376 ? . 2_456 H(10) O(6) 3.206 ? . 3_556 H(10) N(2) 3.104 ? . 2_456 H(10) C(1) 3.321 ? . 2_456 H(10) C(5) 3.459 ? . 1_455 H(10) C(8) 3.201 ? . 2_456 H(10) H(1) 2.848 ? . 2_456 H(10) H(5) 2.592 ? . 1_455 H(10) H(11) 3.311 ? . 3_556 H(10) H(12) 2.976 ? . 1_455 H(10) H(13) 2.877 ? . 1_455 H(10) H(17) 3.122 ? . 1_455 H(11) O(1) 2.018 ? . 3_546 H(11) O(2) 3.038 ? . 3_546 H(11) N(1) 3.279 ? . 3_546 H(11) C(2) 2.760 ? . 3_546 H(11) C(3) 3.416 ? . 3_546 H(11) C(7) 3.370 ? . 3_546 H(11) H(2) 2.674 ? . 3_546 H(11) H(4) 2.780 ? . 4_565 H(11) H(8) 3.039 ? . 2_556 H(11) H(9) 3.003 ? . 3_546 H(11) H(10) 3.311 ? . 3_546 H(11) H(13) 2.959 ? . 3_646 H(11) H(15) 3.518 ? . 3_646 H(11) H(16) 2.670 ? . 3_546 H(12) O(6) 2.848 ? . 3_656 H(12) H(1) 2.826 ? . 2_556 H(12) H(10) 2.976 ? . 1_655 H(13) O(1) 2.773 ? . 1_655 H(13) O(4) 3.315 ? . 2_556 H(13) O(5) 3.482 ? . 1_655 H(13) O(6) 3.149 ? . 3_656 H(13) N(1) 3.586 ? . 1_655 H(13) N(3) 3.438 ? . 3_656 H(13) C(2) 3.550 ? . 1_655 H(13) C(9) 3.581 ? . 3_656 H(13) H(1) 3.486 ? . 2_556 H(13) H(2) 3.441 ? . 1_655 H(13) H(8) 3.495 ? . 4_565 H(13) H(10) 2.877 ? . 1_655 H(13) H(11) 2.959 ? . 3_656 H(14) O(2) 3.289 ? . 3_646 H(14) O(3) 2.892 ? . 2_556 H(14) O(4) 2.899 ? . 2_556 H(14) O(5) 2.786 ? . 1_655 H(14) C(3) 3.415 ? . 3_646 H(14) C(4) 3.539 ? . 2_556 H(14) C(6) 3.544 ? . 2_556 H(14) H(3) 2.801 ? . 3_646 H(14) H(7) 2.916 ? . 2_556 H(14) H(16) 2.842 ? . 3_646 H(14) H(17) 2.565 ? . 2_556 H(15) O(2) 2.848 ? . 3_646 H(15) O(5) 3.347 ? . 1_655 H(15) C(3) 3.409 ? . 3_646 H(15) C(6) 3.222 ? . 4_565 H(15) C(7) 3.106 ? . 4_565 H(15) H(3) 2.963 ? . 3_646 H(15) H(6) 2.850 ? . 4_565 H(15) H(7) 2.822 ? . 4_565 H(15) H(8) 2.521 ? . 4_565 H(15) H(9) 2.911 ? . 4_565 H(15) H(11) 3.518 ? . 3_656 H(15) H(16) 2.615 ? . 3_646 H(16) O(3) 3.246 ? . 2_466 H(16) O(5) 1.970 ? . 3_556 H(16) N(3) 2.988 ? . 3_556 H(16) C(5) 3.377 ? . 2_466 H(16) C(8) 2.668 ? . 3_556 H(16) C(12) 3.153 ? . 3_656 H(16) H(2) 3.408 ? . 3_556 H(16) H(4) 2.959 ? . 2_466 H(16) H(5) 3.345 ? . 2_466 H(16) H(8) 3.402 ? . 2_566 H(16) H(9) 3.020 ? . 2_566 H(16) H(11) 2.670 ? . 3_556 H(16) H(14) 2.842 ? . 3_656 H(16) H(15) 2.615 ? . 3_656 H(16) H(17) 3.291 ? . 4_565 H(17) O(5) 2.215 ? . 2_556 H(17) C(2) 3.225 ? . 4_564 H(17) C(3) 3.572 ? . 4_564 H(17) C(7) 3.501 ? . 1_655 H(17) C(8) 3.147 ? . 2_556 H(17) C(12) 3.525 ? . 2_456 H(17) H(1) 3.364 ? . 2_556 H(17) H(2) 2.322 ? . 4_564 H(17) H(3) 3.291 ? . 4_564 H(17) H(8) 3.141 ? . 1_655 H(17) H(10) 3.122 ? . 1_655 H(17) H(14) 2.565 ? . 2_456 H(17) H(16) 3.291 ? . 4_564 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_angle_DHA _geom_hbond_publ_flag O(2) H(16) O(5) . . 3_556 2.7858(15) 0.840 1.970 163.6 no O(3) H(17) O(5) . . 2_556 3.0146(15) 0.840 2.215 159.1 no N(3) H(11) O(1) . . 3_546 2.8973(16) 0.880 2.018 177.2 no #===END========================================================================