data_global # 1. SUBMISSION DETAILS _publ_contact_author ; Dr. Andew D. Hamilton Department of Chemistry Yale University 225 Prospect St PO Box 208107 New Haven, CT 06520-8107 USA ; _publ_contact_author_phone '+203 432 5570' _publ_contact_author_fax '+203 432 6144' _publ_contact_author_email andrew.hamilton@yale.edu _publ_requested_journal 'JACS' # 2. TITLE AND AUTHOR LIST _publ_section_title ; Alkyne-linked 2,2-disubstituted-indolin-3-one oligomers as extended beta-strand mimetics ; loop_ _publ_author_name _publ_author_address 'Wyrembak, P. N.' ; Department of Chemistry Yale University 225 Prospect St PO Box 208107 New Haven, CT 06520-8107 USA ; 'Hamilton, A. D.' ; Department of Chemistry Yale University 225 Prospect St PO Box 208107 New Haven, CT 06520-8107 USA ; # 3. Results data_pw02 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H22 N2 O3' _chemical_formula_weight 374.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.677(2) _cell_length_b 16.749(3) _cell_length_c 20.009(4) _cell_angle_alpha 90.00 _cell_angle_beta 94.81(3) _cell_angle_gamma 90.00 _cell_volume 3899.6(13) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow-orange- _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.276 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1584 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9873 _exptl_absorpt_correction_T_max 0.9915 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16118 _diffrn_reflns_av_R_equivalents 0.0662 _diffrn_reflns_av_sigmaI/netI 0.1589 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 28.95 _reflns_number_total 10195 _reflns_number_gt 4640 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement Denzo _computing_data_reduction Denzo _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0370P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10195 _refine_ls_number_parameters 521 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1773 _refine_ls_R_factor_gt 0.0628 _refine_ls_wR_factor_ref 0.1213 _refine_ls_wR_factor_gt 0.0990 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _refine_ls_shift/su_max 0.057 _refine_ls_shift/su_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.65896(12) 0.71727(8) 0.41444(6) 0.0430(4) Uani 1 1 d . . . O2 O 0.86983(12) 0.78381(8) 0.15300(6) 0.0379(4) Uani 1 1 d . . . O3 O 0.93644(11) 0.93207(8) -0.10342(6) 0.0364(4) Uani 1 1 d . . . N1 N 0.73051(14) 0.79849(9) 0.26084(8) 0.0330(4) Uani 1 1 d . . . H1 H 0.7736(16) 0.8010(11) 0.2230(9) 0.049(6) Uiso 1 1 d . . . N2 N 0.95972(14) 0.80958(9) -0.00955(8) 0.0299(4) Uani 1 1 d . . . H2 H 1.0176(15) 0.8055(11) -0.0398(9) 0.040(6) Uiso 1 1 d . . . C1 C 0.60286(16) 0.90086(12) 0.39350(9) 0.0336(5) Uani 1 1 d . . . H1A H 0.5788 0.8878 0.4363 0.040 Uiso 1 1 calc R . . C2 C 0.58940(17) 0.97720(13) 0.36849(10) 0.0365(5) Uani 1 1 d . . . H2A H 0.5551 1.0170 0.3941 0.044 Uiso 1 1 calc R . . C3 C 0.62571(16) 0.99643(12) 0.30592(9) 0.0341(5) Uani 1 1 d . . . H3A H 0.6160 1.0496 0.2900 0.041 Uiso 1 1 calc R . . C4 C 0.67565(16) 0.94063(11) 0.26604(9) 0.0280(5) Uani 1 1 d . . . C5 C 0.68811(16) 0.86236(11) 0.29135(9) 0.0269(5) Uani 1 1 d . . . C6 C 0.73180(17) 0.72802(11) 0.30365(9) 0.0292(5) Uani 1 1 d . . . C7 C 0.67727(16) 0.75972(12) 0.36578(9) 0.0317(5) Uani 1 1 d . . . C8 C 0.65245(16) 0.84312(11) 0.35489(9) 0.0283(5) Uani 1 1 d . . . C9 C 0.65702(18) 0.66213(12) 0.27062(10) 0.0398(6) Uani 1 1 d . . . H9A H 0.6925 0.6419 0.2313 0.060 Uiso 1 1 calc R . . H9B H 0.5807 0.6836 0.2566 0.060 Uiso 1 1 calc R . . H9C H 0.6497 0.6186 0.3027 0.060 Uiso 1 1 calc R . . C10 C 0.85421(17) 0.69985(13) 0.32260(9) 0.0395(6) Uani 1 1 d . . . H10A H 0.8874 0.6792 0.2827 0.059 Uiso 1 1 calc R . . H10B H 0.8535 0.6575 0.3563 0.059 Uiso 1 1 calc R . . H10C H 0.9006 0.7447 0.3410 0.059 Uiso 1 1 calc R . . C11 C 0.71401(16) 0.95467(11) 0.20109(10) 0.0296(5) Uani 1 1 d . . . C12 C 0.75156(16) 0.95313(11) 0.14715(10) 0.0285(5) Uani 1 1 d . . . C13 C 0.79733(15) 0.95035(11) 0.08285(9) 0.0269(5) Uani 1 1 d . . . C14 C 0.78648(16) 1.01334(12) 0.03832(9) 0.0334(5) Uani 1 1 d . . . H14A H 0.7474 1.0603 0.0504 0.040 Uiso 1 1 calc R . . C15 C 0.83199(16) 1.00968(12) -0.02465(9) 0.0334(5) Uani 1 1 d . . . H15A H 0.8227 1.0541 -0.0541 0.040 Uiso 1 1 calc R . . C16 C 0.88918(16) 0.94361(12) -0.04420(9) 0.0290(5) Uani 1 1 d . . . C17 C 0.90447(16) 0.87912(11) 0.00102(9) 0.0261(5) Uani 1 1 d . . . C18 C 0.95892(16) 0.75838(11) 0.04963(9) 0.0280(5) Uani 1 1 d . . . C19 C 0.89079(16) 0.80835(11) 0.09697(9) 0.0277(5) Uani 1 1 d . . . C20 C 0.85825(15) 0.88185(11) 0.06315(9) 0.0239(4) Uani 1 1 d . . . C21 C 0.89035(18) 0.68268(12) 0.03253(10) 0.0398(6) Uani 1 1 d . . . H21A H 0.9319 0.6494 0.0023 0.060 Uiso 1 1 calc R . . H21B H 0.8150 0.6969 0.0105 0.060 Uiso 1 1 calc R . . H21C H 0.8800 0.6530 0.0738 0.060 Uiso 1 1 calc R . . C22 C 1.07882(17) 0.74122(13) 0.08160(9) 0.0390(5) Uani 1 1 d . . . H22A H 1.1192 0.7917 0.0915 0.059 Uiso 1 1 calc R . . H22B H 1.1212 0.7096 0.0506 0.059 Uiso 1 1 calc R . . H22C H 1.0735 0.7112 0.1233 0.059 Uiso 1 1 calc R . . C23 C 0.92271(18) 0.99425(12) -0.15239(9) 0.0424(6) Uani 1 1 d . . . H23A H 0.9602 0.9786 -0.1924 0.064 Uiso 1 1 calc R . . H23B H 0.9578 1.0435 -0.1338 0.064 Uiso 1 1 calc R . . H23C H 0.8407 1.0033 -0.1645 0.064 Uiso 1 1 calc R . . O1' O 0.33744(12) 0.23311(9) 0.08911(6) 0.0495(4) Uani 1 1 d . . . O2' O 0.13471(12) 0.21031(8) 0.36276(6) 0.0373(4) Uani 1 1 d . . . O3' O 0.02841(12) 0.08182(8) 0.62051(6) 0.0385(4) Uani 1 1 d . . . N1' N 0.26498(14) 0.17946(10) 0.25044(8) 0.0337(4) Uani 1 1 d . . . H1' H 0.2252(16) 0.1886(11) 0.2915(9) 0.046(6) Uiso 1 1 d . . . N2' N 0.02160(15) 0.19731(10) 0.51980(8) 0.0345(4) Uani 1 1 d . . . H2' H -0.0333(15) 0.2077(11) 0.5503(8) 0.036(6) Uiso 1 1 d . . . C1' C 0.40291(17) 0.05659(13) 0.13376(10) 0.0396(6) Uani 1 1 d . . . H1'A H 0.4274 0.0622 0.0899 0.048 Uiso 1 1 calc R . . C2' C 0.41934(17) -0.01388(14) 0.16828(10) 0.0418(6) Uani 1 1 d . . . H2'A H 0.4562 -0.0573 0.1483 0.050 Uiso 1 1 calc R . . C3' C 0.38243(16) -0.02243(12) 0.23255(10) 0.0369(5) Uani 1 1 d . . . H3'A H 0.3942 -0.0721 0.2551 0.044 Uiso 1 1 calc R . . C4' C 0.32898(16) 0.03927(12) 0.26472(9) 0.0294(5) Uani 1 1 d . . . C5' C 0.31337(16) 0.11179(12) 0.22934(9) 0.0275(5) Uani 1 1 d . . . C6' C 0.26235(17) 0.24188(12) 0.19937(9) 0.0327(5) Uani 1 1 d . . . C7' C 0.32036(17) 0.20015(13) 0.14238(10) 0.0351(5) Uani 1 1 d . . . C8' C 0.34928(16) 0.12010(13) 0.16441(9) 0.0327(5) Uani 1 1 d . . . C9' C 0.13978(17) 0.26489(13) 0.17598(9) 0.0406(6) Uani 1 1 d . . . H9'A H 0.1042 0.2915 0.2126 0.061 Uiso 1 1 calc R . . H9'B H 0.0959 0.2168 0.1626 0.061 Uiso 1 1 calc R . . H9'C H 0.1401 0.3013 0.1376 0.061 Uiso 1 1 calc R . . C10' C 0.33431(18) 0.31372(12) 0.22396(10) 0.0436(6) Uani 1 1 d . . . H10D H 0.2975 0.3404 0.2601 0.065 Uiso 1 1 calc R . . H10E H 0.3404 0.3512 0.1868 0.065 Uiso 1 1 calc R . . H10F H 0.4113 0.2958 0.2407 0.065 Uiso 1 1 calc R . . C11' C 0.28781(16) 0.03403(11) 0.32998(10) 0.0291(5) Uani 1 1 d . . . C12' C 0.24636(16) 0.03989(11) 0.38239(9) 0.0290(5) Uani 1 1 d . . . C13' C 0.19268(15) 0.04809(11) 0.44372(9) 0.0277(5) Uani 1 1 d . . . C14' C 0.19541(16) -0.01155(12) 0.49114(9) 0.0333(5) Uani 1 1 d . . . H14B H 0.2348 -0.0598 0.4833 0.040 Uiso 1 1 calc R . . C15' C 0.14138(16) -0.00286(12) 0.55092(10) 0.0341(5) Uani 1 1 d . . . H15B H 0.1451 -0.0454 0.5825 0.041 Uiso 1 1 calc R . . C16' C 0.08356(16) 0.06548(12) 0.56464(9) 0.0298(5) Uani 1 1 d . . . C17' C 0.07684(16) 0.12660(11) 0.51595(9) 0.0268(5) Uani 1 1 d . . . C18' C 0.03151(16) 0.24428(12) 0.45884(9) 0.0285(5) Uani 1 1 d . . . C19' C 0.10617(16) 0.19044(11) 0.41828(9) 0.0273(5) Uani 1 1 d . . . C20' C 0.13126(15) 0.11859(11) 0.45690(9) 0.0250(4) Uani 1 1 d . . . C21' C -0.08428(17) 0.25844(13) 0.42069(9) 0.0397(6) Uani 1 1 d . . . H21D H -0.1309 0.2930 0.4471 0.059 Uiso 1 1 calc R . . H21E H -0.1236 0.2072 0.4125 0.059 Uiso 1 1 calc R . . H21F H -0.0732 0.2842 0.3777 0.059 Uiso 1 1 calc R . . C22' C 0.09583(18) 0.32162(11) 0.47532(10) 0.0387(5) Uani 1 1 d . . . H22D H 0.0486 0.3566 0.5011 0.058 Uiso 1 1 calc R . . H22E H 0.1122 0.3484 0.4336 0.058 Uiso 1 1 calc R . . H22F H 0.1682 0.3098 0.5019 0.058 Uiso 1 1 calc R . . C23' C 0.03333(18) 0.02223(13) 0.67200(9) 0.0432(6) Uani 1 1 d . . . H23D H -0.0088 0.0410 0.7094 0.065 Uiso 1 1 calc R . . H23E H 0.1137 0.0122 0.6880 0.065 Uiso 1 1 calc R . . H23F H -0.0016 -0.0273 0.6539 0.065 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0425(9) 0.0518(10) 0.0367(8) 0.0104(8) 0.0143(7) 0.0027(8) O2 0.0491(10) 0.0360(9) 0.0305(8) 0.0067(7) 0.0150(7) 0.0106(7) O3 0.0419(9) 0.0406(9) 0.0273(7) 0.0098(7) 0.0062(7) -0.0016(7) N1 0.0450(11) 0.0272(10) 0.0289(9) 0.0019(8) 0.0150(9) 0.0041(8) N2 0.0352(10) 0.0307(10) 0.0250(9) 0.0050(8) 0.0103(8) 0.0044(8) C1 0.0295(12) 0.0416(14) 0.0301(11) -0.0064(10) 0.0055(10) -0.0035(10) C2 0.0322(12) 0.0399(14) 0.0382(12) -0.0171(11) 0.0078(10) -0.0025(10) C3 0.0300(12) 0.0302(12) 0.0419(13) -0.0072(10) 0.0028(10) -0.0002(10) C4 0.0251(11) 0.0287(12) 0.0301(11) -0.0033(9) 0.0020(9) -0.0024(9) C5 0.0233(11) 0.0298(12) 0.0278(11) -0.0062(9) 0.0039(9) -0.0025(9) C6 0.0330(12) 0.0272(11) 0.0282(11) 0.0021(9) 0.0064(9) 0.0001(9) C7 0.0270(12) 0.0417(14) 0.0267(11) 0.0013(10) 0.0041(9) -0.0042(10) C8 0.0250(11) 0.0328(13) 0.0273(11) -0.0045(9) 0.0036(9) -0.0021(9) C9 0.0406(14) 0.0354(13) 0.0440(13) -0.0006(11) 0.0070(11) -0.0003(11) C10 0.0382(13) 0.0465(14) 0.0346(12) 0.0023(10) 0.0069(10) 0.0071(11) C11 0.0264(11) 0.0234(12) 0.0387(12) -0.0005(10) 0.0003(10) 0.0010(9) C12 0.0269(11) 0.0207(11) 0.0373(12) -0.0014(9) -0.0010(10) 0.0017(9) C13 0.0264(11) 0.0246(12) 0.0294(11) 0.0011(9) 0.0006(9) -0.0035(9) C14 0.0347(12) 0.0272(12) 0.0378(12) -0.0004(10) 0.0012(10) 0.0040(10) C15 0.0374(13) 0.0280(12) 0.0337(12) 0.0084(10) -0.0027(10) -0.0038(10) C16 0.0290(12) 0.0337(13) 0.0242(10) 0.0007(9) 0.0014(9) -0.0070(10) C17 0.0249(11) 0.0249(12) 0.0280(11) 0.0005(9) -0.0003(9) -0.0037(9) C18 0.0316(12) 0.0276(12) 0.0258(10) 0.0024(9) 0.0077(9) 0.0040(9) C19 0.0288(11) 0.0285(12) 0.0262(11) -0.0016(9) 0.0056(9) -0.0033(9) C20 0.0236(11) 0.0232(11) 0.0248(10) 0.0016(9) 0.0009(9) -0.0015(8) C21 0.0462(14) 0.0321(13) 0.0432(13) -0.0048(10) 0.0155(11) -0.0003(11) C22 0.0356(13) 0.0478(14) 0.0343(12) 0.0035(11) 0.0064(10) 0.0114(11) C23 0.0484(14) 0.0478(14) 0.0303(12) 0.0159(11) -0.0011(10) -0.0122(12) O1' 0.0479(10) 0.0697(11) 0.0325(8) 0.0056(8) 0.0124(8) -0.0097(9) O2' 0.0443(9) 0.0383(9) 0.0310(8) 0.0066(7) 0.0132(7) 0.0080(7) O3' 0.0475(9) 0.0433(9) 0.0254(7) 0.0101(7) 0.0065(7) -0.0013(7) N1' 0.0443(11) 0.0309(10) 0.0274(9) -0.0001(8) 0.0131(9) 0.0039(9) N2' 0.0440(11) 0.0332(11) 0.0282(9) 0.0049(8) 0.0139(9) 0.0069(9) C1' 0.0272(12) 0.0585(16) 0.0338(12) -0.0160(12) 0.0060(10) -0.0053(11) C2' 0.0324(13) 0.0481(15) 0.0451(14) -0.0202(12) 0.0040(11) 0.0033(11) C3' 0.0277(12) 0.0369(13) 0.0455(13) -0.0105(11) -0.0005(10) 0.0011(10) C4' 0.0230(11) 0.0323(12) 0.0329(11) -0.0055(10) 0.0024(9) -0.0005(9) C5' 0.0224(11) 0.0334(12) 0.0268(10) -0.0076(10) 0.0021(9) -0.0017(9) C6' 0.0363(13) 0.0372(13) 0.0255(10) 0.0033(10) 0.0070(10) -0.0024(10) C7' 0.0259(12) 0.0520(15) 0.0276(11) -0.0013(11) 0.0036(9) -0.0099(10) C8' 0.0227(11) 0.0451(14) 0.0305(11) -0.0060(10) 0.0039(9) -0.0039(10) C9' 0.0373(14) 0.0480(14) 0.0367(12) 0.0011(11) 0.0038(10) -0.0008(11) C10' 0.0460(14) 0.0417(14) 0.0432(13) 0.0002(11) 0.0050(11) -0.0040(12) C11' 0.0248(11) 0.0235(11) 0.0384(12) -0.0008(9) -0.0012(10) 0.0010(9) C12' 0.0249(11) 0.0248(12) 0.0370(12) -0.0006(9) 0.0011(10) 0.0022(9) C13' 0.0234(11) 0.0291(12) 0.0302(11) 0.0004(10) -0.0001(9) -0.0012(9) C14' 0.0298(12) 0.0261(12) 0.0431(13) 0.0019(10) -0.0019(10) 0.0023(9) C15' 0.0327(12) 0.0328(13) 0.0354(12) 0.0111(10) -0.0046(10) -0.0006(10) C16' 0.0282(12) 0.0353(13) 0.0258(11) 0.0041(10) 0.0017(9) -0.0039(10) C17' 0.0261(11) 0.0274(12) 0.0265(11) -0.0007(9) 0.0004(9) -0.0030(9) C18' 0.0327(12) 0.0301(12) 0.0234(10) 0.0042(9) 0.0070(9) 0.0045(9) C19' 0.0253(11) 0.0319(12) 0.0247(10) -0.0002(9) 0.0017(9) -0.0026(9) C20' 0.0243(11) 0.0259(12) 0.0244(10) 0.0002(9) 0.0005(9) -0.0017(9) C21' 0.0324(13) 0.0477(14) 0.0393(12) -0.0019(11) 0.0060(10) 0.0079(11) C22' 0.0503(14) 0.0311(13) 0.0351(12) -0.0004(10) 0.0060(11) 0.0004(11) C23' 0.0461(14) 0.0523(15) 0.0309(12) 0.0176(11) 0.0006(10) -0.0044(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C7 1.239(2) . ? O2 C19 1.2377(19) . ? O3 C16 1.362(2) . ? O3 C23 1.430(2) . ? N1 H1 0.945(18) . ? N1 C5 1.346(2) . ? N1 C6 1.458(2) . ? N2 H2 0.947(17) . ? N2 C17 1.356(2) . ? N2 C18 1.463(2) . ? C1 C2 1.377(3) . ? C1 C8 1.394(2) . ? C2 C3 1.393(2) . ? C3 C4 1.389(2) . ? C4 C5 1.408(3) . ? C4 C11 1.429(2) . ? C5 C8 1.408(2) . ? C6 C10 1.523(3) . ? C6 C9 1.523(3) . ? C6 C7 1.538(2) . ? C7 C8 1.439(3) . ? C11 C12 1.199(2) . ? C12 C13 1.435(2) . ? C13 C14 1.380(2) . ? C13 C20 1.423(2) . ? C14 C15 1.409(2) . ? C15 C16 1.367(3) . ? C16 C17 1.411(3) . ? C17 C20 1.397(2) . ? C18 C22 1.517(3) . ? C18 C21 1.523(3) . ? C18 C19 1.535(2) . ? C19 C20 1.440(3) . ? O1' C7' 1.231(2) . ? O2' C19' 1.232(2) . ? O3' C16' 1.364(2) . ? O3' C23' 1.432(2) . ? N1' H1' 0.989(18) . ? N1' C5' 1.350(2) . ? N1' C6' 1.460(2) . ? N2' H2' 0.938(17) . ? N2' C17' 1.354(2) . ? N2' C18' 1.464(2) . ? C1' C2' 1.373(3) . ? C1' C8' 1.401(3) . ? C2' C3' 1.398(3) . ? C3' C4' 1.392(2) . ? C4' C5' 1.410(3) . ? C4' C11' 1.432(2) . ? C5' C8' 1.405(2) . ? C6' C9' 1.518(3) . ? C6' C10' 1.525(3) . ? C6' C7' 1.542(3) . ? C7' C8' 1.443(3) . ? C11' C12' 1.195(2) . ? C12' C13' 1.431(2) . ? C13' C14' 1.376(2) . ? C13' C20' 1.418(2) . ? C14' C15' 1.406(2) . ? C15' C16' 1.368(3) . ? C16' C17' 1.411(2) . ? C17' C20' 1.394(2) . ? C18' C21' 1.515(3) . ? C18' C22' 1.520(3) . ? C18' C19' 1.533(2) . ? C19' C20' 1.447(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16 O3 C23 117.55(16) . . ? H1 N1 C5 124.7(12) . . ? H1 N1 C6 121.8(12) . . ? C5 N1 C6 111.28(14) . . ? H2 N2 C17 122.5(11) . . ? H2 N2 C18 121.9(11) . . ? C17 N2 C18 109.99(14) . . ? C2 C1 C8 118.87(17) . . ? C1 C2 C3 120.48(18) . . ? C4 C3 C2 122.35(19) . . ? C3 C4 C5 117.10(16) . . ? C3 C4 C11 126.20(18) . . ? C5 C4 C11 116.69(16) . . ? N1 C5 C8 112.05(17) . . ? N1 C5 C4 127.40(16) . . ? C8 C5 C4 120.54(17) . . ? N1 C6 C10 111.12(16) . . ? N1 C6 C9 110.75(16) . . ? C10 C6 C9 112.06(17) . . ? N1 C6 C7 102.18(15) . . ? C10 C6 C7 110.45(16) . . ? C9 C6 C7 109.85(15) . . ? O1 C7 C8 129.06(17) . . ? O1 C7 C6 123.22(18) . . ? C8 C7 C6 107.72(15) . . ? C1 C8 C5 120.65(18) . . ? C1 C8 C7 132.62(17) . . ? C5 C8 C7 106.73(16) . . ? C12 C11 C4 168.9(2) . . ? C11 C12 C13 179.2(2) . . ? C14 C13 C20 117.29(16) . . ? C14 C13 C12 122.23(17) . . ? C20 C13 C12 120.48(16) . . ? C13 C14 C15 121.54(18) . . ? C16 C15 C14 121.41(18) . . ? O3 C16 C15 127.39(18) . . ? O3 C16 C17 114.24(17) . . ? C15 C16 C17 118.36(16) . . ? N2 C17 C20 113.02(16) . . ? N2 C17 C16 126.42(16) . . ? C20 C17 C16 120.54(17) . . ? N2 C18 C22 112.59(15) . . ? N2 C18 C21 110.18(16) . . ? C22 C18 C21 112.71(17) . . ? N2 C18 C19 102.63(15) . . ? C22 C18 C19 110.54(16) . . ? C21 C18 C19 107.61(15) . . ? O2 C19 C20 130.17(17) . . ? O2 C19 C18 122.01(17) . . ? C20 C19 C18 107.81(15) . . ? C17 C20 C13 120.83(17) . . ? C17 C20 C19 106.48(16) . . ? C13 C20 C19 132.62(16) . . ? C16' O3' C23' 117.18(15) . . ? H1' N1' C5' 128.9(11) . . ? H1' N1' C6' 119.1(11) . . ? C5' N1' C6' 111.53(15) . . ? H2' N2' C17' 123.7(11) . . ? H2' N2' C18' 123.3(11) . . ? C17' N2' C18' 110.56(15) . . ? C2' C1' C8' 118.76(18) . . ? C1' C2' C3' 120.67(19) . . ? C2' C3' C4' 122.3(2) . . ? C3' C4' C5' 116.83(17) . . ? C3' C4' C11' 125.03(19) . . ? C5' C4' C11' 118.14(17) . . ? N1' C5' C8' 111.79(18) . . ? N1' C5' C4' 127.32(16) . . ? C8' C5' C4' 120.89(17) . . ? N1' C6' C9' 111.18(16) . . ? N1' C6' C10' 111.12(16) . . ? C9' C6' C10' 112.26(17) . . ? N1' C6' C7' 102.02(16) . . ? C9' C6' C7' 110.40(16) . . ? C10' C6' C7' 109.38(16) . . ? O1' C7' C8' 129.08(18) . . ? O1' C7' C6' 123.37(19) . . ? C8' C7' C6' 107.54(16) . . ? C1' C8' C5' 120.5(2) . . ? C1' C8' C7' 132.34(18) . . ? C5' C8' C7' 107.11(17) . . ? C12' C11' C4' 170.7(2) . . ? C11' C12' C13' 177.7(2) . . ? C14' C13' C20' 117.33(16) . . ? C14' C13' C12' 122.36(17) . . ? C20' C13' C12' 120.29(17) . . ? C13' C14' C15' 121.69(18) . . ? C16' C15' C14' 121.43(18) . . ? O3' C16' C15' 127.38(17) . . ? O3' C16' C17' 114.69(17) . . ? C15' C16' C17' 117.92(16) . . ? N2' C17' C20' 112.69(17) . . ? N2' C17' C16' 126.49(16) . . ? C20' C17' C16' 120.82(18) . . ? N2' C18' C21' 111.98(16) . . ? N2' C18' C22' 110.45(15) . . ? C21' C18' C22' 112.33(17) . . ? N2' C18' C19' 102.31(15) . . ? C21' C18' C19' 110.40(16) . . ? C22' C18' C19' 108.88(15) . . ? O2' C19' C20' 130.41(17) . . ? O2' C19' C18' 121.82(17) . . ? C20' C19' C18' 107.77(15) . . ? C17' C20' C13' 120.77(17) . . ? C17' C20' C19' 106.64(16) . . ? C13' C20' C19' 132.56(16) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 28.95 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.223 _refine_diff_density_min -0.208 _refine_diff_density_rms 0.048