Supplementary Material for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Ling Peng' _publ_contact_author_address ; Departement de chimie CNRS UMR 6114 163, avenue de Luminy Marseille 13288 FRANCE ; _publ_contact_author_email LING.PENG@UNIVMED.FR _publ_section_title ; Synthesis of Bitriazolyl Nucleosides and Unexpectedly Different Reactivity of Azidotriazole Nucleoside Isomers in Huisgen Reaction ; _publ_contact_author ; Ling Peng ; loop_ _publ_author_name 'Ling Peng.' 'Charles Berro' 'Zhijin Fan.' 'Wei Li.' 'Xiufeng Liu.' 'Fanqi Qu.' ; E.Rauzy ; 'Yi Xia.' data_2a _database_code_depnum_ccdc_archive 'CCDC 639564' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2' _symmetry_Int_Tables_number 5 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,y,-z 3 1/2+x,1/2+y,z 4 1/2-x,1/2+y,-z _cell_length_a 11.8185(4) _cell_length_b 11.0156(4) _cell_length_c 18.8659(8) _cell_angle_alpha 90.00 _cell_angle_beta 95.528(3) _cell_angle_gamma 90.00 _cell_volume 2444.69 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z O1 O 0.09683(18) 0.5371(2) 0.25281(10) O2 O 0.1946(2) 0.7458(2) 0.18032(14) O3 O 0.1472(3) 0.8313(4) 0.2804(2) O4 O 0.1455(2) 0.4605(3) 0.07573(11) O5 O 0.3251(3) 0.4405(7) 0.0575(2) O6 O 0.0982(2) 0.2906(2) 0.17114(11) O7 O 0.2278(5) 0.1696(5) 0.1306(3) O8 O 0.08810(17) 0.3531(2) 0.41358(11) O9 O 0.24181(17) 0.31952(19) 0.49134(10) O10 O 0.85051(19) 0.5569(2) 0.46588(13) O11 O 0.88460(16) 0.6570(2) 0.36676(11) N1 N 0.25091(17) 0.4457(2) 0.31822(11) N2 N 0.34513(19) 0.4966(2) 0.29461(12) N3 N 0.37552(17) 0.4540(2) 0.41238(11) N4 N 0.52567(18) 0.5439(2) 0.35348(11) N5 N 0.5564(2) 0.6130(3) 0.29845(13) N6 N 0.6633(2) 0.6371(3) 0.31236(13) C1 C 0.1512(2) 0.4248(3) 0.26721(14) H1 H 0.1003 0.3686 0.2871 C2 C 0.1848(2) 0.3746(3) 0.19644(14) H2 H 0.2594 0.3378 0.2023 C3 C 0.1774(3) 0.4879(3) 0.14958(14) H3 H 0.2443 0.5351 0.1575 C4 C 0.0828(3) 0.5602(3) 0.17787(16) H4 H 0.0119 0.5285 0.1550 C5 C 0.0826(4) 0.6949(4) 0.1651(2) H5A H 0.0555 0.7112 0.1158 H5B H 0.0309 0.7336 0.1951 C6 C 0.2162(4) 0.8116(3) 0.23958(19) C7 C 0.3354(4) 0.8566(5) 0.2478(3) H7A H 0.3355 0.9437 0.2461 H7B H 0.3756 0.8251 0.2099 H7C H 0.3722 0.8301 0.2927 C8 C 0.2291(4) 0.4393(6) 0.0349(2) C9 C 0.1855(6) 0.4114(8) -0.0396(2) H9A H 0.2039 0.4768 -0.0700 H9B H 0.1044 0.4015 -0.0425 H9C H 0.2197 0.3378 -0.0544 C10 C 0.1320(5) 0.1885(4) 0.1390(2) C11 C 0.0316(6) 0.1096(6) 0.1178(3) H11A H -0.0179 0.1500 0.0819 H11B H -0.0088 0.0940 0.1586 H11C H 0.0569 0.0342 0.0993 C12 C 0.2711(2) 0.4198(2) 0.38803(13) C13 C 0.1875(2) 0.3616(2) 0.43172(13) C14 C 0.1716(3) 0.2647(3) 0.54161(17) H14A H 0.1075 0.3162 0.5472 H14B H 0.2154 0.2549 0.5868 H14C H 0.1453 0.1868 0.5241 C15 C 0.4148(2) 0.4984(2) 0.35288(13) C16 C 0.6150(2) 0.5258(2) 0.40267(14) H16 H 0.6104 0.4714 0.4455 C17 C 0.7017(2) 0.5850(2) 0.37542(14) C18 C 0.8200(2) 0.5969(2) 0.40831(15) C19 C 1.0022(2) 0.6735(4) 0.3953(2) H19A H 1.0054 0.7275 0.4354 H19B H 1.0447 0.7075 0.3592 H19C H 1.0342 0.5964 0.4101 #END # Attachment '2i.cif' data_2i _database_code_depnum_ccdc_archive 'CCDC 639565' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-[4-(4-Methoxyphenyl)-1H-1,2,3-triazol-1-yl]-1-(2,3,5-tri-O-acetyl-beta- D-ribofuranosyl)-1,2,4-triazole-5-carboxylic acid methyl ester ; _chemical_name_common ; 3-(4-(4-Methoxyphenyl)-1H-1,2,3-triazol-1-yl)-1-(2,3,5-tri-O- acetyl-beta-D-ribofuranosyl)-1,2,4-triazole-5-carboxylic acid methyl ester ; _chemical_melting_point 163 _chemical_formula_moiety ? _chemical_formula_sum 'C24 H26 N6 O10' _chemical_formula_weight 558.51 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' O O 0.0106 0.0060 '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 7.53960(10) _cell_length_b 7.9351(2) _cell_length_c 43.1982(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2584.44(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 15226 _cell_measurement_theta_min 0.47 _cell_measurement_theta_max 28.24 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max .5 _exptl_crystal_size_mid .4 _exptl_crystal_size_min .2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.435 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 0.114 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 KappaCCD _diffrn_measurement_method 'Phi + omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15226 _diffrn_reflns_av_R_equivalents 0.033 _diffrn_reflns_av_sigmaI/netI 0.0277 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 56 _diffrn_reflns_theta_min 0.94 _diffrn_reflns_theta_max 28.24 _reflns_number_total 3426 _reflns_number_gt 2946 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KappaCCD (Bruker-Nonius, 1998)' _computing_cell_refinement 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _publ_section_references ; Altamore, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. and Camalli, M. J. Appl. Cryst. (1994) 27, 435-436 Bruker-Nonius (1998). Kappa CCD Reference Manual. Nonius B.V., P.O. Box 811, 2600 Av, Delft, The Netherlands. Otwinowski, Z. and Minor, W. " Processing of X-ray Diffraction Data Collected in Oscillation Mode ", Methods in Enzymology, Volume 276: Macromolecular Crystallography, part A, p.307-326, 1997,C.W. Carter, Jr. & R.M. Sweet, Eds., Academic Press. Sheldrick, G.M. (1997). SHELXL97. Program for the refinement of crystal structures. Univ. of G\"ottingen, Germany. ; _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^)+(0.1151P)^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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.54(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -2.0(15) _refine_ls_number_reflns 3426 _refine_ls_number_parameters 362 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0859 _refine_ls_R_factor_gt 0.0613 _refine_ls_wR_factor_ref 0.1791 _refine_ls_wR_factor_gt 0.1449 _refine_ls_goodness_of_fit_ref 1.317 _refine_ls_restrained_S_all 1.317 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.931 _diffrn_reflns_theta_full 28.24 _diffrn_measured_fraction_theta_full 0.931 _refine_diff_density_max 0.651 _refine_diff_density_min -0.664 _refine_diff_density_rms 0.200 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 0.7743(3) -0.0497(3) 0.10326(5) 0.0459(5) Uani 1 1 d . . . O2 O 0.7052(3) 0.2657(3) 0.07176(6) 0.0549(6) Uani 1 1 d . . . O3 O 0.4983(4) 0.2657(5) 0.10914(8) 0.0794(9) Uani 1 1 d . . . O4 O 1.0016(3) -0.0536(3) 0.03124(5) 0.0491(6) Uani 1 1 d . . . O5 O 1.2399(4) 0.1136(4) 0.02876(8) 0.0808(10) Uani 1 1 d . . . O6 O 1.0626(3) -0.2845(3) 0.07500(5) 0.0457(5) Uani 1 1 d . . . O7 O 1.3441(4) -0.2606(4) 0.05925(8) 0.0791(9) Uani 1 1 d . . . O8 O 0.8956(4) -0.2733(3) 0.17694(6) 0.0553(6) Uani 1 1 d . . . O9 O 0.9828(3) -0.1173(3) 0.21738(5) 0.0567(6) Uani 1 1 d . . . O10 O 1.6227(5) 1.2165(4) 0.21553(7) 0.0789(9) Uani 1 1 d . . . N1 N 1.0058(3) 0.0091(3) 0.13741(5) 0.0387(5) Uani 1 1 d . . . N2 N 1.0690(4) 0.1607(3) 0.12770(6) 0.0428(6) Uani 1 1 d . . . N3 N 1.0876(3) 0.1420(3) 0.18022(5) 0.0393(5) Uani 1 1 d . . . N4 N 1.1843(3) 0.3952(3) 0.15478(6) 0.0398(5) Uani 1 1 d . . . N5 N 1.1710(4) 0.4951(3) 0.12955(6) 0.0506(7) Uani 1 1 d . . . N6 N 1.2504(4) 0.6360(3) 0.13631(7) 0.0495(7) Uani 1 1 d . . . C1 C 0.9418(4) -0.1088(4) 0.11394(6) 0.0392(6) Uani 1 1 d . . . H1 H 0.9295 -0.2218 0.1228 0.047 Uiso 1 1 calc R . . C2 C 1.0655(4) -0.1137(3) 0.08586(6) 0.0393(6) Uani 1 1 d . . . H2 H 1.1855 -0.0741 0.0907 0.047 Uiso 1 1 calc R . . C3 C 0.9706(4) -0.0018(3) 0.06244(6) 0.0399(6) Uani 1 1 d . . . H3 H 1.0025 0.1169 0.0654 0.048 Uiso 1 1 calc R . . C4 C 0.7756(4) -0.0322(4) 0.07041(7) 0.0435(6) Uani 1 1 d . . . H4 H 0.7382 -0.1391 0.0611 0.052 Uiso 1 1 calc R . . C5 C 0.6464(5) 0.1037(5) 0.06097(9) 0.0569(9) Uani 1 1 d . . . H5A H 0.6358 0.1056 0.0386 0.068 Uiso 1 1 calc R . . H5B H 0.5305 0.0790 0.0696 0.068 Uiso 1 1 calc R . . C6 C 0.6201(5) 0.3324(5) 0.09665(8) 0.0552(8) Uani 1 1 d . . . C7 C 0.6974(7) 0.4973(6) 0.10581(12) 0.0754(12) Uani 1 1 d . . . H7A H 0.6746 0.5789 0.0899 0.113 Uiso 1 1 calc R . . H7B H 0.8231 0.4853 0.1086 0.113 Uiso 1 1 calc R . . H7C H 0.6444 0.5341 0.1249 0.113 Uiso 1 1 calc R . . C8 C 1.1479(5) 0.0094(4) 0.01720(8) 0.0496(7) Uani 1 1 d . . . C9 C 1.1810(6) -0.0758(6) -0.01308(9) 0.0716(11) Uani 1 1 d . . . H9A H 1.2378 0.0016 -0.0270 0.107 Uiso 1 1 calc R . . H9B H 1.0702 -0.1119 -0.0218 0.107 Uiso 1 1 calc R . . H9C H 1.2563 -0.1719 -0.0099 0.107 Uiso 1 1 calc R . . C10 C 1.2131(6) -0.3440(5) 0.06211(8) 0.0561(9) Uani 1 1 d . . . C11 C 1.1899(7) -0.5225(5) 0.05213(11) 0.0740(12) Uani 1 1 d . . . H11A H 1.2515 -0.5404 0.0330 0.111 Uiso 1 1 calc R . . H11B H 1.0660 -0.5458 0.0493 0.111 Uiso 1 1 calc R . . H11C H 1.2373 -0.5962 0.0677 0.111 Uiso 1 1 calc R . . C12 C 1.0182(3) -0.0011(3) 0.16885(6) 0.0375(6) Uani 1 1 d . . . C13 C 0.9583(4) -0.1483(4) 0.18748(7) 0.0412(6) Uani 1 1 d . . . C14 C 0.9348(7) -0.2548(6) 0.23812(9) 0.0735(11) Uani 1 1 d . . . H14A H 0.8098 -0.2764 0.2365 0.110 Uiso 1 1 calc R . . H14B H 0.9635 -0.2243 0.2590 0.110 Uiso 1 1 calc R . . H14C H 0.9994 -0.3544 0.2324 0.110 Uiso 1 1 calc R . . C15 C 1.1151(4) 0.2315(3) 0.15409(7) 0.0385(6) Uani 1 1 d . . . C16 C 1.2731(4) 0.4753(4) 0.17792(7) 0.0407(6) Uani 1 1 d . . . H16 H 1.2989 0.4344 0.1976 0.049 Uiso 1 1 calc R . . C17 C 1.3158(4) 0.6291(4) 0.16581(7) 0.0399(6) Uani 1 1 d . . . C18 C 1.4054(4) 0.7777(4) 0.17858(7) 0.0401(6) Uani 1 1 d . . . C19 C 1.4192(5) 0.8034(4) 0.21028(7) 0.0511(8) Uani 1 1 d . . . H19 H 1.3783 0.7213 0.2239 0.061 Uiso 1 1 calc R . . C20 C 1.4935(5) 0.9502(5) 0.22191(8) 0.0591(9) Uani 1 1 d . . . H20 H 1.5008 0.9663 0.2432 0.071 Uiso 1 1 calc R . . C21 C 1.5574(5) 1.0738(4) 0.20184(8) 0.0510(8) Uani 1 1 d . . . C22 C 1.5491(4) 1.0469(4) 0.17039(8) 0.0493(7) Uani 1 1 d . . . H22 H 1.5945 1.1270 0.1568 0.059 Uiso 1 1 calc R . . C23 C 1.4733(4) 0.9006(4) 0.15891(7) 0.0464(7) Uani 1 1 d . . . H23 H 1.4677 0.8843 0.1376 0.056 Uiso 1 1 calc R . . C24 C 1.6979(5) 1.3441(5) 0.19659(11) 0.0665(10) Uani 1 1 d . . . H24A H 1.7993 1.2997 0.1859 0.100 Uiso 1 1 calc R . . H24B H 1.7337 1.4374 0.2093 0.100 Uiso 1 1 calc R . . H24C H 1.6115 1.3815 0.1818 0.100 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 0.0419(10) 0.0563(12) 0.0395(11) 0.0002(10) 0.0008(8) -0.0002(10) O2 0.0596(13) 0.0490(12) 0.0563(14) 0.0043(11) 0.0063(11) 0.0085(12) O3 0.0722(16) 0.0823(19) 0.084(2) 0.0137(17) 0.0252(15) 0.0039(18) O4 0.0633(12) 0.0517(11) 0.0323(11) -0.0047(9) 0.0017(9) -0.0078(11) O5 0.0847(19) 0.0744(18) 0.083(2) -0.0221(16) 0.0255(16) -0.0255(17) O6 0.0572(12) 0.0367(10) 0.0430(11) -0.0057(9) 0.0003(9) 0.0033(10) O7 0.0669(16) 0.0699(18) 0.100(2) -0.0141(18) 0.0266(15) 0.0083(16) O8 0.0746(14) 0.0437(11) 0.0476(13) 0.0008(10) 0.0040(11) -0.0086(12) O9 0.0728(14) 0.0605(14) 0.0368(12) 0.0083(10) -0.0017(10) -0.0143(13) O10 0.112(2) 0.0601(15) 0.0643(18) -0.0148(13) -0.0001(16) -0.0324(18) N1 0.0472(12) 0.0349(11) 0.0340(12) -0.0016(9) 0.0001(9) -0.0008(10) N2 0.0555(14) 0.0358(11) 0.0371(13) -0.0006(10) -0.0001(10) -0.0042(11) N3 0.0438(11) 0.0387(11) 0.0353(12) -0.0020(9) 0.0001(9) 0.0030(10) N4 0.0454(12) 0.0377(11) 0.0364(12) -0.0018(9) -0.0038(9) 0.0002(10) N5 0.0659(16) 0.0410(13) 0.0448(15) 0.0022(11) -0.0128(12) -0.0043(13) N6 0.0630(16) 0.0401(12) 0.0454(15) 0.0017(11) -0.0108(11) -0.0037(12) C1 0.0467(13) 0.0365(12) 0.0345(13) -0.0019(11) -0.0014(10) -0.0017(12) C2 0.0458(13) 0.0367(13) 0.0354(13) -0.0057(11) -0.0002(10) 0.0001(12) C3 0.0501(14) 0.0370(13) 0.0326(13) -0.0031(11) 0.0005(10) -0.0016(12) C4 0.0468(14) 0.0435(14) 0.0402(15) -0.0025(12) -0.0051(11) -0.0015(13) C5 0.0548(17) 0.063(2) 0.0533(19) -0.0012(16) -0.0138(14) 0.0096(17) C6 0.0550(17) 0.0560(18) 0.0545(19) 0.0098(15) 0.0059(14) 0.0158(16) C7 0.084(3) 0.063(2) 0.079(3) -0.011(2) 0.006(2) 0.008(2) C8 0.0593(17) 0.0499(16) 0.0397(16) 0.0009(13) 0.0028(12) -0.0023(16) C9 0.085(3) 0.089(3) 0.0412(19) -0.0088(19) 0.0103(17) -0.006(3) C10 0.072(2) 0.0483(17) 0.0479(18) -0.0071(14) 0.0045(15) 0.0164(18) C11 0.101(3) 0.0507(19) 0.071(3) -0.0174(18) 0.006(2) 0.019(2) C12 0.0398(12) 0.0400(14) 0.0327(13) -0.0012(10) 0.0012(10) 0.0046(12) C13 0.0445(13) 0.0427(14) 0.0364(14) 0.0036(12) 0.0006(11) 0.0067(12) C14 0.098(3) 0.079(3) 0.0441(19) 0.0195(19) -0.0002(18) -0.021(3) C15 0.0415(12) 0.0359(12) 0.0383(13) -0.0021(10) -0.0006(10) 0.0036(12) C16 0.0447(13) 0.0419(13) 0.0356(14) -0.0011(11) -0.0029(10) -0.0012(12) C17 0.0397(12) 0.0411(14) 0.0391(14) -0.0011(11) -0.0012(10) 0.0025(12) C18 0.0390(12) 0.0410(14) 0.0405(14) -0.0003(11) -0.0014(10) 0.0020(12) C19 0.0618(18) 0.0498(16) 0.0417(16) 0.0027(13) -0.0049(13) -0.0088(16) C20 0.080(2) 0.0594(19) 0.0378(16) -0.0030(15) -0.0058(15) -0.0128(19) C21 0.0540(16) 0.0456(15) 0.0535(19) -0.0069(14) -0.0023(14) -0.0063(14) C22 0.0513(16) 0.0494(16) 0.0473(17) 0.0024(14) 0.0052(13) -0.0069(14) C23 0.0483(15) 0.0505(16) 0.0405(16) -0.0016(13) 0.0014(12) -0.0032(14) C24 0.0560(18) 0.0460(16) 0.098(3) -0.0083(19) 0.0068(19) -0.0037(17) _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 C1 1.423(3) . ? O1 C4 1.426(4) . ? O2 C6 1.359(4) . ? O2 C5 1.438(5) . ? O3 C6 1.189(5) . ? O4 C8 1.354(4) . ? O4 C3 1.428(3) . ? O5 C8 1.189(4) . ? O6 C10 1.349(4) . ? O6 C2 1.434(3) . ? O7 C10 1.196(5) . ? O8 C13 1.190(4) . ? O9 C13 1.328(4) . ? O9 C14 1.458(4) . ? O10 C21 1.369(4) . ? O10 C24 1.420(5) . ? N1 N2 1.360(3) . ? N1 C12 1.364(4) . ? N1 C1 1.462(4) . ? N2 C15 1.317(4) . ? N3 C12 1.343(4) . ? N3 C15 1.349(4) . ? N4 N5 1.352(4) . ? N4 C16 1.360(4) . ? N4 C15 1.401(4) . ? N5 N6 1.301(4) . ? N6 C17 1.368(4) . ? C1 C2 1.531(4) . ? C1 H1 0.9800 . ? C2 C3 1.525(4) . ? C2 H2 0.9800 . ? C3 C4 1.529(4) . ? C3 H3 0.9800 . ? C4 C5 1.509(5) . ? C4 H4 0.9800 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.486(6) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 C9 1.493(5) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.491(5) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C13 1.488(4) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C16 C17 1.367(4) . ? C16 H16 0.9300 . ? C17 C18 1.466(4) . ? C18 C23 1.391(4) . ? C18 C19 1.389(4) . ? C19 C20 1.387(5) . ? C19 H19 0.9300 . ? C20 C21 1.394(5) . ? C20 H20 0.9300 . ? C21 C22 1.377(5) . ? C22 C23 1.386(5) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? 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 C1 O1 C4 110.4(2) . . ? C6 O2 C5 117.3(3) . . ? C8 O4 C3 116.7(2) . . ? C10 O6 C2 116.9(3) . . ? C13 O9 C14 115.1(3) . . ? C21 O10 C24 119.0(3) . . ? N2 N1 C12 109.6(2) . . ? N2 N1 C1 117.9(2) . . ? C12 N1 C1 132.5(2) . . ? C15 N2 N1 101.7(2) . . ? C12 N3 C15 101.5(2) . . ? N5 N4 C16 110.8(2) . . ? N5 N4 C15 119.9(2) . . ? C16 N4 C15 129.2(3) . . ? N6 N5 N4 106.8(2) . . ? N5 N6 C17 109.9(3) . . ? O1 C1 N1 107.9(2) . . ? O1 C1 C2 107.0(2) . . ? N1 C1 C2 111.4(2) . . ? O1 C1 H1 110.2 . . ? N1 C1 H1 110.2 . . ? C2 C1 H1 110.2 . . ? O6 C2 C3 109.0(2) . . ? O6 C2 C1 105.9(2) . . ? C3 C2 C1 103.0(2) . . ? O6 C2 H2 112.7 . . ? C3 C2 H2 112.7 . . ? C1 C2 H2 112.7 . . ? O4 C3 C2 112.5(2) . . ? O4 C3 C4 108.9(2) . . ? C2 C3 C4 102.1(2) . . ? O4 C3 H3 111.0 . . ? C2 C3 H3 111.0 . . ? C4 C3 H3 111.0 . . ? O1 C4 C5 109.5(3) . . ? O1 C4 C3 104.2(2) . . ? C5 C4 C3 116.5(3) . . ? O1 C4 H4 108.8 . . ? C5 C4 H4 108.8 . . ? C3 C4 H4 108.8 . . ? O2 C5 C4 110.7(3) . . ? O2 C5 H5A 109.5 . . ? C4 C5 H5A 109.5 . . ? O2 C5 H5B 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 108.1 . . ? O3 C6 O2 123.4(4) . . ? O3 C6 C7 125.0(4) . . ? O2 C6 C7 111.6(3) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O5 C8 O4 122.9(3) . . ? O5 C8 C9 125.8(4) . . ? O4 C8 C9 111.2(3) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O7 C10 O6 122.9(3) . . ? O7 C10 C11 126.4(4) . . ? O6 C10 C11 110.7(4) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N3 C12 N1 109.9(2) . . ? N3 C12 C13 125.7(3) . . ? N1 C12 C13 124.3(3) . . ? O8 C13 O9 125.6(3) . . ? O8 C13 C12 124.6(3) . . ? O9 C13 C12 109.8(3) . . ? O9 C14 H14A 109.5 . . ? O9 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O9 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N2 C15 N3 117.3(3) . . ? N2 C15 N4 120.8(3) . . ? N3 C15 N4 121.8(3) . . ? N4 C16 C17 104.6(3) . . ? N4 C16 H16 127.7 . . ? C17 C16 H16 127.7 . . ? N6 C17 C16 107.9(3) . . ? N6 C17 C18 119.0(3) . . ? C16 C17 C18 133.1(3) . . ? C23 C18 C19 118.1(3) . . ? C23 C18 C17 120.2(3) . . ? C19 C18 C17 121.6(3) . . ? C20 C19 C18 120.8(3) . . ? C20 C19 H19 119.6 . . ? C18 C19 H19 119.6 . . ? C19 C20 C21 120.3(3) . . ? C19 C20 H20 119.8 . . ? C21 C20 H20 119.8 . . ? O10 C21 C22 124.8(3) . . ? O10 C21 C20 115.9(3) . . ? C22 C21 C20 119.2(3) . . ? C21 C22 C23 120.1(3) . . ? C21 C22 H22 119.9 . . ? C23 C22 H22 119.9 . . ? C22 C23 C18 121.4(3) . . ? C22 C23 H23 119.3 . . ? C18 C23 H23 119.3 . . ? O10 C24 H24A 109.5 . . ? O10 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O10 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ?