# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 #TrackingRef 'web_deposit_cif_file_0_PawelGrobelny_1289286463.cif' _audit_creation_date 'Nov 08 14:14:28 2010' _audit_creation_method 'PLATON option' _audit_update_record ? _publ_contact_author_name 'Prof. G. R. Desiraju' _publ_contact_author_address ; Prof. G. R. Desiraju Solid State and Structural Chemistry Unit Indian Institute of Science Bangalore ; _publ_contact_author_email desiraju@sscu.iisc.ernet.in _publ_contact_author_fax '+91 80 23602306' _publ_contact_author_phone '+91 80 22933311' _publ_contact_letter ; Submission dated :2010-11-07 Please consider this CIF for submission to the Cambridge Crystallographic Data Centre. I certify that all authors have seen and approved of this submission, that all have made significant scientific contributions to the work reported, and that all share responsibility and accountability for the results. This CIF is submitted as part of a journal submission ; #=============================================================================== _publ_section_title ; Drug-drug co-crystals. Temperature-dependent proton mobility \ in the molecular complex of isoniazid with 4-aminosalicylic acid. ; _publ_section_title_footnote ; ; loop_ _publ_author_name _publ_author_footnote _publ_author_address 'Pawel Grobelny' ; Solid state and Structural Chemistry Unit Indian Institut of Science Bangalore 560 012 India ; 'Arijit Mukherjee' 'Arijit Mukherjee' 'Prof. Gautam R. Desiraju' ; Solid state and Structural Chemistry Unit Indian Institut of Science Bangalore 560 012 India ; 'Gautam R. Desiraju' '' '' #=============================================================================== _publ_section_references ; Allen, F.H. (2002). Acta Cryst. B58, 380-388. Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., Giacovazzo, C. Guagliardi, A., Moliterni, A.G.G., Polidori, G. & Spagna, R. (1999) J. Appl. Cryst. 32, 115-119. Beurskens, P.T., Beurskens, G., de Gelder, R., Garc\'ia-Granda, S., Gould, R.O., Israel, R. & Smits, J.M.M. (1999) The DIRDIF99 Program System, Technical Report of the Crystallography Laboratory, University of Nijmegen, The Netherlands. Boer, J.L. de & Duisenberg, A.J.M. (1984). Acta Cryst. A40, C-410. Boeyens, J.C.A. (1978). J.Cryst.Mol.Struct. 8, 317-320. Cremer, D. & Pople, J.A. (1975). J. Am. Chem. Soc. 97, 1354-1358. Duisenberg, A.J.M. (1992). J. Appl. Cryst. 25, 92-96. Duisenberg, A.J.M., Kroon-Batenburg, L.M.J. & Schreurs, A.M.M. (2003). J. Appl. Cryst. 36, 220-229. Enraf-Nonius (1989). CAD-4 Software. Version 5. Enraf-Nonius, Delft, The Netherlands. Flack, H.D. (1983). Acta Cryst. A39, 876-881. Hooft, R.W.W. (1998). Collect Software, Nonius B.V., Delft, The Netherlands. LePage, Y. (1987). J. Appl. Cryst. 20, 264-269. Mackay, A.L. (1984). Acta Cryst. A40, 165-166. Meulenaer, J. de & Tompa, H. (1965). Acta Cryst. 19, 1014-1018. North, A.C.T., Phillips, D.C. & Mathews, F.S. (1968). Acta Cryst. A24, 351-359. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C.W. Carter & R.M. Sweet, pp. 307-326. London: Academic Press. Sheldrick, G.M. (1986). SHELXS86. University of G\"ottingen, Germany. Sheldrick, G.M. (1993). SHELXL93. University of G\"ottingen, Germany. Sheldrick, G.M. (1997). SHELXS97. University of G\"ottingen, Germany. Sheldrick, G.M. (1997). SHELXL97. University of G\"ottingen, Germany. Sluis, P. van der & Spek, A.L. (1990). Acta Cryst. A46, 194-201. Spek, A.L. (1987). Acta Cryst. C43, 1233-1235. Spek, A.L. (1988). J. Appl. Cryst. 21, 578-579. Spek, A.L. (1994). Am. Crystallogr. Assoc.-Abstracts, 22, 66. Spek, A.L. (1997). HELENA, Program for Datareduction, Utrecht University, The Netherlands. Spek, A.L. (2003). J. Appl. Cryst. 36, 7-13. Wilson, A.J.C. (1992). Ed. International Tables for Crystallography, Volume C, Kluwer Academic Publishers, Dordrecht, The Netherlands. ; _publ_section_acknowledgements ; ; _publ_section_figure_captions ; View of the title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level. ; #=============================================================================== data_datam1 _database_code_depnum_ccdc_archive 'CCDC 800230' #TrackingRef 'web_deposit_cif_file_0_PawelGrobelny_1289286463.cif' _chemical_name_systematic ; ; _chemical_name_common 'Isoniazid:4-aminosalicylic acid co-crystal' _chemical_melting_point ? _chemical_formula_moiety 'C13 H14 N4 O4, C7 H7 N O3, C6 H7 N3 O' _chemical_formula_structural ? _chemical_formula_sum 'C26 H28 N8 O8' _chemical_formula_iupac ? _chemical_formula_weight 580.56 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_space_group_name_H-M 'P n a 21' _symmetry_Int_Tables_number 33 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,1/2+z 3 1/2-x,1/2+y,1/2+z 4 1/2+x,1/2-y,z _cell_length_a 21.837(2) _cell_length_b 16.5073(14) _cell_length_c 7.2252(6) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2604.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6976 _cell_measurement_theta_min 1.9 _cell_measurement_theta_max 27.5 _cell_special_details ; ; _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.481 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 0.113 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.851 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' #=============================================================================== _exptl_special_details ; ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_source 'Sealed Tube' _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_measurement_specimen_support Fiber _diffrn_detector CCD _diffrn_measurement_device ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_detector_area_resol_mean 13.6612 _diffrn_measurement_method 'profile data from \w-scans' _diffrn_reflns_number 26874 _diffrn_reflns_av_R_equivalents 0.0440 _diffrn_reflns_av_sigmaI/netI 0.0225 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3226 _reflns_number_gt 3097 _reflns_threshold_expression >2\s(I) _diffrn_measurement_details ? _diffrn_orient_matrix_UB_11 0.014889 _diffrn_orient_matrix_UB_12 -0.136586 _diffrn_orient_matrix_UB_13 0.016688 _diffrn_orient_matrix_UB_21 0.060160 _diffrn_orient_matrix_UB_22 0.006809 _diffrn_orient_matrix_UB_23 0.002057 _diffrn_orient_matrix_UB_31 -0.002156 _diffrn_orient_matrix_UB_32 0.005316 _diffrn_orient_matrix_UB_33 0.045433 _diffrn_orient_matrix_type d*Trek _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.998 _computing_data_collection ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== _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^ > 2\s(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^)+(0.0703P)^2^+0.3138P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3226 _refine_ls_number_parameters 492 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0392 _refine_ls_R_factor_gt 0.0358 _refine_ls_wR_factor_ref 0.1101 _refine_ls_wR_factor_gt 0.1000 _refine_ls_goodness_of_fit_ref 1.138 _refine_ls_restrained_S_all 1.138 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.248 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.059 #=============================================================================== loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags O2 O Uani 0.11409(7) 0.10490(10) 0.5851(3) 1.000 0.0294(5) . . O6 O Uani 0.31633(8) 0.50589(10) 0.5112(3) 1.000 0.0289(5) . . O7 O Uani 0.22069(7) 0.53665(9) 0.5984(3) 1.000 0.0285(5) . . O8 O Uani 0.39845(7) 0.61627(11) 0.5095(3) 1.000 0.0283(5) . . N4 N Uani 0.20071(9) 0.38462(11) 0.5896(3) 1.000 0.0233(5) . . N5 N Uani 0.21613(9) 0.08068(11) 0.5702(3) 1.000 0.0239(5) . . N6 N Uani 0.21063(10) -0.00563(11) 0.5725(4) 1.000 0.0287(6) . . N8 N Uani 0.33283(10) 0.89149(12) 0.5813(3) 1.000 0.0275(6) . . C7 C Uani 0.24356(10) 0.33356(14) 0.6546(3) 1.000 0.0226(6) . . C8 C Uani 0.23549(10) 0.24999(13) 0.6530(3) 1.000 0.0215(6) . . C9 C Uani 0.18119(10) 0.21870(12) 0.5823(3) 1.000 0.0195(5) . . C10 C Uani 0.13665(10) 0.27183(14) 0.5185(3) 1.000 0.0211(6) . . C11 C Uani 0.14803(10) 0.35488(14) 0.5238(3) 1.000 0.0235(6) . . C12 C Uani 0.16733(10) 0.12896(13) 0.5789(3) 1.000 0.0215(6) . . C20 C Uani 0.29248(9) 0.64292(12) 0.5815(3) 1.000 0.0207(6) . . C21 C Uani 0.35261(10) 0.67038(14) 0.5460(3) 1.000 0.0216(6) . . C22 C Uani 0.36619(10) 0.75238(14) 0.5460(3) 1.000 0.0229(6) . . C23 C Uani 0.32047(10) 0.81018(13) 0.5834(3) 1.000 0.0225(6) . . C24 C Uani 0.26107(10) 0.78301(13) 0.6295(3) 1.000 0.0218(6) . . C25 C Uani 0.24827(10) 0.70115(13) 0.6279(3) 1.000 0.0210(6) . . C26 C Uani 0.27688(10) 0.55664(13) 0.5626(3) 1.000 0.0229(6) . . O3 O Uani 0.42425(7) 0.00133(9) 0.3852(3) 1.000 0.0301(5) . . O4 O Uani 0.52200(7) 0.03564(9) 0.3305(3) 1.000 0.0286(5) . . O5 O Uani 0.34727(7) 0.11554(10) 0.4644(3) 1.000 0.0262(5) . . N7 N Uani 0.40888(10) 0.38889(12) 0.3546(4) 1.000 0.0284(6) . . C13 C Uani 0.44966(10) 0.14031(13) 0.3521(3) 1.000 0.0202(5) . . C14 C Uani 0.39165(10) 0.16843(13) 0.4079(3) 1.000 0.0212(6) . . C15 C Uani 0.37844(10) 0.25059(13) 0.4087(3) 1.000 0.0213(6) . . C16 C Uani 0.42244(10) 0.30738(12) 0.3546(3) 1.000 0.0213(6) . . C17 C Uani 0.48022(10) 0.27972(13) 0.2947(3) 1.000 0.0220(6) . . C18 C Uani 0.49299(9) 0.19821(14) 0.2946(3) 1.000 0.0209(6) . . C19 C Uani 0.46426(10) 0.05342(13) 0.3564(3) 1.000 0.0229(6) . . O1 O Uani 0.37578(7) 0.40071(10) 0.8293(3) 1.000 0.0299(5) . . N1 N Uani 0.45612(9) 0.11753(11) 0.8415(3) 1.000 0.0235(5) . . N2 N Uani 0.47760(9) 0.42170(11) 0.8486(4) 1.000 0.0281(6) . . N3 N Uani 0.47350(10) 0.50731(12) 0.8480(4) 1.000 0.0332(7) . . C1 C Uani 0.50044(11) 0.16683(14) 0.7805(3) 1.000 0.0241(6) . . C2 C Uani 0.49474(10) 0.25029(14) 0.7763(3) 1.000 0.0215(6) . . C3 C Uani 0.44018(9) 0.28425(13) 0.8376(3) 1.000 0.0208(6) . . C4 C Uani 0.39368(10) 0.23346(14) 0.8998(3) 1.000 0.0229(6) . . C5 C Uani 0.40325(10) 0.15038(14) 0.9002(4) 1.000 0.0235(6) . . C6 C Uani 0.42811(10) 0.37384(13) 0.8385(4) 1.000 0.0224(6) . . H5N H Uiso 0.2569(14) 0.0998(17) 0.556(5) 1.000 0.035(8) . . H6A H Uiso 0.1839(16) -0.020(2) 0.488(5) 1.000 0.033(8) . . H6B H Uiso 0.201(3) -0.026(3) 0.700(10) 1.000 0.102(19) . . H7 H Uiso 0.2807(14) 0.3567(18) 0.699(5) 1.000 0.036(8) . . H7O H Uiso 0.212(2) 0.462(3) 0.601(9) 1.000 0.104(17) . . H8 H Uiso 0.2677(13) 0.2145(16) 0.705(4) 1.000 0.026(7) . . H8A H Uiso 0.3655(17) 0.908(2) 0.537(6) 1.000 0.048(10) . . H8B H Uiso 0.2994(14) 0.9251(17) 0.587(5) 1.000 0.028(7) . . H8O H Uiso 0.3744(19) 0.565(2) 0.510(7) 1.000 0.073(13) . . H10 H Uiso 0.0974(13) 0.2515(18) 0.463(5) 1.000 0.030(8) . . H11 H Uiso 0.1206(12) 0.3955(16) 0.466(4) 1.000 0.020(6) . . H22 H Uiso 0.4049(14) 0.7718(18) 0.516(5) 1.000 0.035(8) . . H24 H Uiso 0.2285(15) 0.823(2) 0.649(6) 1.000 0.048(10) . . H25 H Uiso 0.2048(13) 0.6770(16) 0.655(5) 1.000 0.031(7) . . H4O H Uiso 0.5335(18) -0.021(2) 0.332(8) 1.000 0.066(12) . . H5O H Uiso 0.3621(15) 0.0615(19) 0.451(6) 1.000 0.045(9) . . H7A H Uiso 0.4409(15) 0.4261(19) 0.337(6) 1.000 0.040(8) . . H7B H Uiso 0.3758(15) 0.4032(18) 0.422(5) 1.000 0.033(8) . . H15 H Uiso 0.3356(14) 0.2659(18) 0.438(5) 1.000 0.034(8) . . H17 H Uiso 0.5100(14) 0.3172(17) 0.263(5) 1.000 0.029(8) . . H18 H Uiso 0.5301(11) 0.1792(14) 0.254(4) 1.000 0.011(6) . . H1 H Uiso 0.5372(12) 0.1361(16) 0.738(4) 1.000 0.022(7) . . H2 H Uiso 0.5243(14) 0.2788(18) 0.737(5) 1.000 0.036(9) . . H2N H Uiso 0.5149(16) 0.405(2) 0.867(6) 1.000 0.045(9) . . H3A H Uiso 0.4448(17) 0.520(2) 0.950(6) 1.000 0.043(9) . . H3B H Uiso 0.4532(17) 0.516(2) 0.743(6) 1.000 0.043(10) . . H4 H Uiso 0.3557(15) 0.254(2) 0.940(5) 1.000 0.044(10) . . H5 H Uiso 0.3717(13) 0.1109(16) 0.939(4) 1.000 0.025(7) . . 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 O2 0.0176(7) 0.0245(8) 0.0462(10) -0.0021(8) 0.0019(8) -0.0047(6) O6 0.0221(8) 0.0225(8) 0.0421(10) 0.0007(7) 0.0035(8) 0.0053(6) O7 0.0210(8) 0.0204(7) 0.0441(10) -0.0021(8) 0.0049(8) -0.0011(6) O8 0.0154(7) 0.0297(8) 0.0397(10) -0.0026(8) 0.0011(7) 0.0033(6) N4 0.0220(9) 0.0198(8) 0.0281(10) -0.0009(8) 0.0028(9) -0.0018(7) N5 0.0205(9) 0.0170(8) 0.0341(11) 0.0011(9) 0.0027(9) -0.0012(7) N6 0.0303(10) 0.0161(8) 0.0397(13) -0.0001(9) 0.0008(10) -0.0027(7) N8 0.0245(10) 0.0234(9) 0.0347(11) 0.0014(9) 0.0028(10) -0.0062(8) C7 0.0196(10) 0.0222(10) 0.0259(11) -0.0021(9) 0.0007(9) -0.0028(8) C8 0.0172(10) 0.0238(11) 0.0234(12) 0.0004(9) 0.0008(9) -0.0020(8) C9 0.0184(9) 0.0196(9) 0.0206(10) 0.0005(9) 0.0026(9) -0.0024(7) C10 0.0149(9) 0.0248(10) 0.0235(11) -0.0002(9) 0.0031(9) -0.0031(8) C11 0.0202(10) 0.0233(10) 0.0271(11) 0.0012(9) 0.0031(9) 0.0011(8) C12 0.0199(10) 0.0209(9) 0.0238(11) 0.0009(9) 0.0026(9) -0.0019(8) C20 0.0169(9) 0.0227(10) 0.0224(10) 0.0011(9) -0.0017(9) -0.0007(8) C21 0.0164(10) 0.0280(11) 0.0204(10) -0.0008(9) -0.0003(8) 0.0025(8) C22 0.0169(9) 0.0286(11) 0.0231(11) -0.0008(9) 0.0006(9) -0.0051(8) C23 0.0212(10) 0.0258(10) 0.0205(10) -0.0001(9) -0.0003(9) -0.0051(8) C24 0.0190(10) 0.0210(10) 0.0254(12) 0.0015(9) -0.0004(9) -0.0013(8) C25 0.0181(10) 0.0211(10) 0.0237(12) 0.0005(9) -0.0002(9) -0.0007(8) C26 0.0200(10) 0.0217(10) 0.0270(11) 0.0012(9) -0.0009(9) 0.0012(8) O3 0.0208(8) 0.0221(7) 0.0474(12) 0.0046(8) 0.0014(8) -0.0030(6) O4 0.0190(7) 0.0191(7) 0.0476(11) 0.0006(8) 0.0021(8) 0.0007(6) O5 0.0161(7) 0.0254(8) 0.0370(9) 0.0004(8) 0.0046(7) -0.0044(6) N7 0.0241(10) 0.0210(9) 0.0400(12) 0.0004(9) 0.0034(10) 0.0015(8) C13 0.0176(9) 0.0202(9) 0.0229(10) 0.0000(9) -0.0009(9) -0.0023(8) C14 0.0165(9) 0.0248(10) 0.0223(10) 0.0006(9) -0.0010(9) -0.0037(8) C15 0.0157(9) 0.0239(10) 0.0242(11) -0.0016(9) -0.0005(9) -0.0012(8) C16 0.0202(10) 0.0221(10) 0.0216(10) 0.0006(9) -0.0023(9) -0.0002(8) C17 0.0192(10) 0.0233(10) 0.0235(11) 0.0033(9) -0.0005(9) -0.0049(8) C18 0.0137(9) 0.0275(11) 0.0215(11) 0.0010(9) 0.0009(9) -0.0018(8) C19 0.0195(10) 0.0226(10) 0.0267(11) 0.0003(10) -0.0003(9) -0.0010(8) O1 0.0193(8) 0.0276(8) 0.0429(11) -0.0035(8) -0.0039(8) 0.0031(6) N1 0.0211(9) 0.0224(8) 0.0270(10) -0.0012(9) -0.0001(8) -0.0011(7) N2 0.0184(9) 0.0200(9) 0.0459(13) -0.0018(10) -0.0032(10) 0.0016(7) N3 0.0243(9) 0.0224(9) 0.0529(16) -0.0022(11) -0.0011(11) -0.0002(7) C1 0.0181(10) 0.0287(11) 0.0256(11) -0.0018(10) 0.0010(9) 0.0010(8) C2 0.0188(10) 0.0249(11) 0.0209(11) -0.0013(9) 0.0008(9) -0.0014(8) C3 0.0179(10) 0.0248(10) 0.0196(10) -0.0013(9) -0.0022(9) -0.0005(8) C4 0.0158(9) 0.0284(11) 0.0244(11) 0.0001(10) -0.0011(9) 0.0015(8) C5 0.0200(10) 0.0235(10) 0.0269(11) 0.0031(9) 0.0007(9) -0.0022(8) C6 0.0200(10) 0.0233(10) 0.0238(11) -0.0014(10) -0.0024(9) 0.0024(8) #=============================================================================== _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; 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 O2 C12 1.229(3) . . yes O6 C26 1.258(3) . . yes O7 C26 1.297(3) . . yes O8 C21 1.367(3) . . yes O7 H7O 1.25(5) . . no O8 H8O 1.00(4) . . no O3 C19 1.243(3) . . yes O4 C19 1.308(3) . . yes O5 C14 1.367(3) . . yes O4 H4O 0.97(3) . . no O5 H5O 0.95(3) . . no O1 C6 1.228(3) . . yes N4 C7 1.344(3) . . yes N4 C11 1.338(3) . . yes N5 N6 1.430(3) . . yes N5 C12 1.332(3) . . yes N8 C23 1.369(3) . . yes N4 H7O 1.30(5) . . no N5 H5N 0.95(3) . . no N6 H6A 0.88(3) . . no N6 H6B 1.00(7) . . no N8 H8A 0.83(4) . . no N8 H8B 0.92(3) . . no N7 C16 1.378(3) . . yes N7 H7B 0.90(3) . . no N7 H7A 0.94(3) . . no N1 C5 1.344(3) . . yes N1 C1 1.339(3) . . yes N2 C6 1.341(3) . . yes N2 N3 1.416(3) . . yes N2 H2N 0.87(4) . . no N3 H3A 0.99(4) . . no N3 H3B 0.89(4) . . no C7 C8 1.391(3) . . no C8 C9 1.391(3) . . no C9 C10 1.388(3) . . no C9 C12 1.512(3) . . no C10 C11 1.394(3) . . no C20 C25 1.403(3) . . no C20 C26 1.471(3) . . no C20 C21 1.413(3) . . no C21 C22 1.386(3) . . no C22 C23 1.407(3) . . no C23 C24 1.412(3) . . no C24 C25 1.380(3) . . no C7 H7 0.95(3) . . no C8 H8 0.99(3) . . no C10 H10 1.00(3) . . no C11 H11 0.99(3) . . no C22 H22 0.93(3) . . no C24 H24 0.98(3) . . no C25 H25 1.05(3) . . no C13 C14 1.408(3) . . no C13 C19 1.470(3) . . no C13 C18 1.408(3) . . no C14 C15 1.387(3) . . no C15 C16 1.398(3) . . no C16 C17 1.410(3) . . no C17 C18 1.374(3) . . no C15 H15 0.99(3) . . no C17 H17 0.93(3) . . no C18 H18 0.92(2) . . no C1 C2 1.384(3) . . no C2 C3 1.389(3) . . no C3 C4 1.391(3) . . no C3 C6 1.502(3) . . no C4 C5 1.387(3) . . no C1 H1 1.00(3) . . no C2 H2 0.85(3) . . no C4 H4 0.94(3) . . no C5 H5 0.99(3) . . 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 C26 O7 H7O 114(2) . . . no C21 O8 H8O 100(2) . . . no C19 O4 H4O 118(2) . . . no C14 O5 H5O 109(2) . . . no C7 N4 C11 119.51(19) . . . yes N6 N5 C12 121.89(19) . . . yes C11 N4 H7O 123(2) . . . no C7 N4 H7O 117(2) . . . no C12 N5 H5N 123.8(17) . . . no N6 N5 H5N 114.3(17) . . . no H6A N6 H6B 114(4) . . . no N5 N6 H6B 111(3) . . . no N5 N6 H6A 109(2) . . . no H8A N8 H8B 120(3) . . . no C23 N8 H8B 115.8(18) . . . no C23 N8 H8A 120(2) . . . no C16 N7 H7A 118.6(19) . . . no H7A N7 H7B 120(3) . . . no C16 N7 H7B 115.3(19) . . . no C1 N1 C5 118.65(19) . . . yes N3 N2 C6 122.48(19) . . . yes C6 N2 H2N 125(2) . . . no N3 N2 H2N 112(2) . . . no N2 N3 H3B 101(2) . . . no N2 N3 H3A 104.4(19) . . . no H3A N3 H3B 107(3) . . . no N4 C7 C8 122.1(2) . . . yes C7 C8 C9 118.7(2) . . . no C8 C9 C12 122.72(19) . . . no C10 C9 C12 118.24(19) . . . no C8 C9 C10 118.99(19) . . . no C9 C10 C11 119.2(2) . . . no N4 C11 C10 121.6(2) . . . yes O2 C12 N5 124.4(2) . . . yes O2 C12 C9 120.34(19) . . . yes N5 C12 C9 115.26(19) . . . yes C25 C20 C26 121.75(18) . . . no C21 C20 C26 120.61(19) . . . no C21 C20 C25 117.59(19) . . . no O8 C21 C22 118.8(2) . . . yes O8 C21 C20 120.4(2) . . . yes C20 C21 C22 120.8(2) . . . no C21 C22 C23 120.7(2) . . . no N8 C23 C22 121.5(2) . . . yes C22 C23 C24 118.8(2) . . . no N8 C23 C24 119.7(2) . . . yes C23 C24 C25 119.7(2) . . . no C20 C25 C24 122.2(2) . . . no O6 C26 C20 120.92(19) . . . yes O7 C26 C20 116.56(18) . . . yes O6 C26 O7 122.5(2) . . . yes C8 C7 H7 120.6(18) . . . no N4 C7 H7 117.3(18) . . . no C7 C8 H8 119.6(16) . . . no C9 C8 H8 121.7(16) . . . no C11 C10 H10 119.5(17) . . . no C9 C10 H10 121.3(17) . . . no C10 C11 H11 123.1(15) . . . no N4 C11 H11 114.9(15) . . . no C21 C22 H22 122.1(18) . . . no C23 C22 H22 117.1(18) . . . no C23 C24 H24 119.1(19) . . . no C25 C24 H24 120.9(19) . . . no C20 C25 H25 114.0(15) . . . no C24 C25 H25 123.7(15) . . . no C14 C13 C18 117.74(19) . . . no C14 C13 C19 120.72(19) . . . no C18 C13 C19 121.54(19) . . . no O5 C14 C13 120.85(19) . . . yes C13 C14 C15 120.7(2) . . . no O5 C14 C15 118.43(19) . . . yes C14 C15 C16 120.8(2) . . . no C15 C16 C17 118.93(19) . . . no N7 C16 C15 120.5(2) . . . yes N7 C16 C17 120.6(2) . . . yes C16 C17 C18 119.93(19) . . . no C13 C18 C17 121.89(19) . . . no O3 C19 O4 123.10(19) . . . yes O4 C19 C13 115.16(19) . . . yes O3 C19 C13 121.7(2) . . . yes C16 C15 H15 122.5(17) . . . no C14 C15 H15 116.5(17) . . . no C16 C17 H17 119.2(18) . . . no C18 C17 H17 120.8(18) . . . no C13 C18 H18 117.1(15) . . . no C17 C18 H18 121.0(15) . . . no N1 C1 C2 123.2(2) . . . yes C1 C2 C3 118.2(2) . . . no C2 C3 C4 119.1(2) . . . no C4 C3 C6 117.63(19) . . . no C2 C3 C6 123.31(19) . . . no C3 C4 C5 119.1(2) . . . no N1 C5 C4 121.8(2) . . . yes O1 C6 C3 121.25(19) . . . yes N2 C6 C3 116.04(19) . . . yes O1 C6 N2 122.7(2) . . . yes N1 C1 H1 111.9(15) . . . no C2 C1 H1 124.9(15) . . . no C1 C2 H2 119(2) . . . no C3 C2 H2 122(2) . . . no C3 C4 H4 122(2) . . . no C5 C4 H4 119(2) . . . no N1 C5 H5 115.0(16) . . . no C4 C5 H5 123.2(16) . . . 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 N4 C7 C8 1.2(3) . . . . no C7 N4 C11 C10 -0.9(3) . . . . no N6 N5 C12 O2 -1.8(4) . . . . no N6 N5 C12 C9 177.8(2) . . . . no C1 N1 C5 C4 -0.3(4) . . . . no C5 N1 C1 C2 0.6(4) . . . . no N3 N2 C6 C3 179.1(3) . . . . no N3 N2 C6 O1 -0.5(5) . . . . no N4 C7 C8 C9 -0.2(3) . . . . no C7 C8 C9 C12 -178.4(2) . . . . no C7 C8 C9 C10 -1.0(3) . . . . no C12 C9 C10 C11 178.8(2) . . . . no C8 C9 C12 O2 151.8(2) . . . . no C8 C9 C10 C11 1.2(3) . . . . no C8 C9 C12 N5 -27.8(3) . . . . no C10 C9 C12 O2 -25.7(3) . . . . no C10 C9 C12 N5 154.8(2) . . . . no C9 C10 C11 N4 -0.3(3) . . . . no C25 C20 C21 C22 -3.9(3) . . . . no C26 C20 C21 O8 -5.8(3) . . . . no C25 C20 C21 O8 176.6(2) . . . . no C21 C20 C26 O7 179.8(2) . . . . no C25 C20 C26 O6 176.1(2) . . . . no C25 C20 C26 O7 -2.7(3) . . . . no C21 C20 C25 C24 3.6(3) . . . . no C26 C20 C25 C24 -174.0(2) . . . . no C26 C20 C21 C22 173.7(2) . . . . no C21 C20 C26 O6 -1.4(3) . . . . no O8 C21 C22 C23 -179.8(2) . . . . no C20 C21 C22 C23 0.7(3) . . . . no C21 C22 C23 N8 -179.0(2) . . . . no C21 C22 C23 C24 2.9(3) . . . . no N8 C23 C24 C25 178.7(2) . . . . no C22 C23 C24 C25 -3.2(3) . . . . no C23 C24 C25 C20 -0.1(3) . . . . no C18 C13 C14 O5 179.6(2) . . . . no C18 C13 C14 C15 -1.1(3) . . . . no C14 C13 C19 O3 9.6(3) . . . . no C14 C13 C19 O4 -169.5(2) . . . . no C18 C13 C19 O3 -171.1(2) . . . . no C18 C13 C19 O4 9.8(3) . . . . no C19 C13 C14 O5 -1.1(3) . . . . no C19 C13 C14 C15 178.2(2) . . . . no C14 C13 C18 C17 1.0(3) . . . . no C19 C13 C18 C17 -178.3(2) . . . . no O5 C14 C15 C16 179.2(2) . . . . no C13 C14 C15 C16 -0.2(3) . . . . no C14 C15 C16 N7 179.6(2) . . . . no C14 C15 C16 C17 1.5(3) . . . . no C15 C16 C17 C18 -1.6(3) . . . . no N7 C16 C17 C18 -179.7(2) . . . . no C16 C17 C18 C13 0.4(3) . . . . no N1 C1 C2 C3 -0.3(3) . . . . no C1 C2 C3 C4 -0.2(3) . . . . no C1 C2 C3 C6 -179.5(2) . . . . no C2 C3 C4 C5 0.5(3) . . . . no C6 C3 C4 C5 179.8(2) . . . . no C2 C3 C6 O1 154.0(3) . . . . no C2 C3 C6 N2 -25.6(4) . . . . no C4 C3 C6 O1 -25.3(4) . . . . no C4 C3 C6 N2 155.1(2) . . . . no C3 C4 C5 N1 -0.3(4) . . . . 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 O1 O6 3.160(3) . . no O1 N3 2.769(3) . . no O1 C7 3.340(3) . . no O1 N6 3.006(3) . 3_555 no O2 O8 3.084(3) . 3_545 no O2 N3 3.031(3) . 3_544 no O2 N6 2.790(3) . . no O3 C1 3.314(3) . 2_654 no O3 O5 2.590(2) . . no O3 N8 3.046(3) . 1_545 no O4 C1 3.397(3) . 2_654 no O4 N1 2.574(2) . 2_654 no O5 O3 2.590(2) . . no O5 N5 3.019(3) . . no O6 C7 3.419(3) . . no O6 N7 3.016(3) . . no O6 N6 3.230(4) . 3_554 no O6 O8 2.557(2) . . no O6 O1 3.160(3) . . no O8 O2 3.084(3) . 3_554 no O8 N2 3.012(3) . 2_664 no O8 O6 2.557(2) . . no O1 H4 2.59(3) . . no O1 H6A 2.17(3) . 3_555 no O1 H3A 2.63(4) . . no O1 H3B 2.62(4) . . no O1 H7 2.39(3) . . no O2 H6A 2.66(3) . . no O2 H3A 2.14(4) . 3_544 no O2 H10 2.60(3) . . no O3 H5O 1.75(3) . . no O3 H1 2.64(3) . 2_654 no O3 H8A 2.29(4) . 1_545 no O4 H11 2.62(3) . 4_555 no O4 H18 2.44(2) . . no O5 H25 2.71(3) . 3_544 no O5 H5N 2.10(3) . . no O6 H7B 2.23(3) . . no O6 H6B 2.34(7) . 3_554 no O6 H7 2.92(3) . . no O6 H8O 1.60(4) . . no O7 H5 2.63(3) . 3_554 no O7 H25 2.38(3) . . no O8 H3B 2.65(4) . . no O8 H2N 2.18(4) . 2_664 no N1 C19 3.316(3) . 2_655 no N1 O4 2.574(2) . 2_655 no N2 O8 3.012(3) . 2_665 no N3 O2 3.031(3) . 3_555 no N3 O1 2.769(3) . . no N3 N7 3.088(3) . 2_665 no N5 O5 3.019(3) . . no N6 O6 3.230(4) . 3_545 no N6 N8 3.164(3) . 1_545 no N6 O1 3.006(3) . 3_544 no N6 O2 2.790(3) . . no N7 O6 3.016(3) . . no N7 N3 3.088(3) . 2_664 no N8 C11 3.281(3) . 3_555 no N8 O3 3.046(3) . 1_565 no N8 N6 3.164(3) . 1_565 no N1 H4O 1.61(3) . 2_655 no N2 H2 2.69(3) . . no N3 H7A 2.17(3) . 2_665 no N5 H8 2.66(3) . . no N6 H24 2.91(3) . 1_545 no N6 H8B 2.25(3) . 1_545 no C1 C14 3.591(3) . . no C1 C13 3.317(3) . . no C1 O4 3.397(3) . 2_655 no C1 C18 3.553(3) . . no C1 O3 3.314(3) . 2_655 no C2 C16 3.559(3) . . no C2 C17 3.528(3) . . no C2 C18 3.585(3) . . no C3 C16 3.532(3) . . no C3 C17 3.417(3) . 1_556 no C3 C15 3.425(3) . . no C4 C17 3.507(3) . 1_556 no C4 C16 3.561(3) . 1_556 no C4 C25 3.551(3) . 3_545 no C4 C15 3.575(3) . . no C5 C14 3.578(4) . . no C5 C13 3.423(4) . 1_556 no C5 C18 3.547(3) . 1_556 no C7 C23 3.421(3) . 3_545 no C7 O1 3.340(3) . . no C7 C24 3.533(3) . 3_545 no C7 O6 3.419(3) . . no C8 C25 3.543(3) . 3_545 no C8 C24 3.487(3) . 3_545 no C8 C23 3.486(3) . 3_545 no C8 C15 3.586(3) . . no C9 C21 3.522(3) . 3_545 no C9 C22 3.550(3) . 3_545 no C10 C24 3.595(3) . 3_544 no C10 C18 3.564(3) . 4_455 no C10 C23 3.341(3) . 3_544 no C10 C22 3.430(3) . 3_544 no C11 C23 3.338(3) . 3_544 no C11 N8 3.281(3) . 3_544 no C12 C21 3.471(3) . 3_545 no C13 C5 3.423(4) . 1_554 no C13 C1 3.317(3) . . no C14 C5 3.578(4) . . no C14 C1 3.591(3) . . no C15 C8 3.586(3) . . no C15 C3 3.425(3) . . no C15 C4 3.575(3) . . no C15 C25 3.527(3) . 3_544 no C16 C4 3.561(3) . 1_554 no C16 C2 3.559(3) . . no C16 C3 3.532(3) . . no C17 C2 3.528(3) . . no C17 C4 3.507(3) . 1_554 no C17 C3 3.417(3) . 1_554 no C18 C1 3.553(3) . . no C18 C5 3.547(3) . 1_554 no C18 C2 3.585(3) . . no C18 C10 3.564(3) . 4_555 no C19 N1 3.316(3) . 2_654 no C21 C9 3.522(3) . 3_554 no C21 C12 3.471(3) . 3_554 no C22 C10 3.430(3) . 3_555 no C22 C9 3.550(3) . 3_554 no C23 C8 3.486(3) . 3_554 no C23 C11 3.338(3) . 3_555 no C23 C7 3.421(3) . 3_554 no C23 C10 3.341(3) . 3_555 no C24 C7 3.533(3) . 3_554 no C24 C8 3.487(3) . 3_554 no C24 C10 3.595(3) . 3_555 no C25 C4 3.551(3) . 3_554 no C25 C15 3.527(3) . 3_555 no C25 C8 3.543(3) . 3_554 no C1 H4O 2.55(3) . 2_655 no C1 H22 2.86(3) . 2_665 no C2 H22 2.82(3) . 2_665 no C2 H2N 2.67(3) . . no C4 H25 2.98(3) . 3_545 no C5 H4O 2.59(4) . 2_655 no C5 H25 3.03(3) . 3_545 no C7 H15 2.78(3) . . no C8 H15 2.70(3) . . no C8 H5N 2.62(3) . . no C10 H1 3.09(3) . 4_455 no C10 H2 3.04(3) . 4_455 no C11 H1 2.88(3) . 4_455 no C14 H25 2.79(3) . 3_544 no C15 H25 2.85(3) . 3_544 no C17 H10 2.88(3) . 4_555 no C18 H10 2.71(3) . 4_555 no C18 H22 3.04(3) . 2_664 no C19 H5O 2.34(3) . . no C22 H18 2.94(3) . 2_665 no C24 H15 3.08(3) . 3_555 no C24 H4 2.93(3) . 3_554 no C25 H8 3.08(3) . 3_554 no C25 H15 3.09(3) . 3_555 no C25 H4 2.79(3) . 3_554 no C26 H8O 2.17(4) . . no C26 H6B 2.99(7) . 3_554 no H1 C10 3.09(3) . 4_555 no H1 O3 2.64(3) . 2_655 no H1 H4O 2.54(5) . 2_655 no H1 C11 2.88(3) . 4_555 no H2 H10 2.59(5) . 4_555 no H2 H2N 2.29(5) . . no H2 C10 3.04(3) . 4_555 no H2 N2 2.69(3) . . no H2N O8 2.18(4) . 2_665 no H2N C2 2.67(3) . . no H2N H2 2.29(5) . . no H3A O2 2.14(4) . 3_555 no H3A O1 2.63(4) . . no H3B O8 2.65(4) . . no H3B H8O 2.54(6) . . no H3B O1 2.62(4) . . no H3B H7A 2.59(5) . 2_665 no H4 O1 2.59(3) . . no H4 C24 2.93(3) . 3_545 no H4 C25 2.79(3) . 3_545 no H4 H25 2.40(5) . 3_545 no H4O C1 2.55(3) . 2_654 no H4O C5 2.59(4) . 2_654 no H4O N1 1.61(3) . 2_654 no H4O H1 2.54(5) . 2_654 no H5 H25 2.53(4) . 3_545 no H5 O7 2.63(3) . 3_545 no H5N H5O 2.50(5) . . no H5N C8 2.62(3) . . no H5N O5 2.10(3) . . no H5N H8 2.19(4) . . no H5O H5N 2.50(5) . . no H5O C19 2.34(3) . . no H5O O3 1.75(3) . . no H6A O1 2.17(3) . 3_544 no H6A O2 2.66(3) . . no H6B H24 2.59(6) . 1_545 no H6B H7B 2.60(7) . 3_545 no H6B O6 2.34(7) . 3_545 no H6B C26 2.99(7) . 3_545 no H6B H8B 2.44(7) . 1_545 no H7 O1 2.39(3) . . no H7 O6 2.92(3) . . no H7A H3B 2.59(5) . 2_664 no H7A H17 2.41(4) . . no H7A N3 2.17(3) . 2_664 no H7B H6B 2.60(7) . 3_554 no H7B H15 2.43(4) . . no H7B O6 2.23(3) . . no H8 H5N 2.19(4) . . no H8 C25 3.08(3) . 3_545 no H8 H15 2.58(4) . . no H8 N5 2.66(3) . . no H8A H22 2.41(4) . . no H8A O3 2.29(4) . 1_565 no H8B H24 2.33(4) . . no H8B H6B 2.44(7) . 1_565 no H8B N6 2.25(3) . 1_565 no H8O C26 2.17(4) . . no H8O O6 1.60(4) . . no H8O H3B 2.54(6) . . no H10 H18 2.40(4) . 4_455 no H10 C17 2.88(3) . 4_455 no H10 O2 2.60(3) . . no H10 H2 2.59(5) . 4_455 no H10 C18 2.71(3) . 4_455 no H11 O4 2.62(3) . 4_455 no H15 H7B 2.43(4) . . no H15 C8 2.70(3) . . no H15 C25 3.09(3) . 3_544 no H15 C24 3.08(3) . 3_544 no H15 C7 2.78(3) . . no H15 H8 2.58(4) . . no H17 H7A 2.41(4) . . no H18 H22 2.37(4) . 2_664 no H18 O4 2.44(2) . . no H18 H10 2.40(4) . 4_555 no H18 C22 2.94(3) . 2_664 no H22 H8A 2.41(4) . . no H22 H18 2.37(4) . 2_665 no H22 C1 2.86(3) . 2_664 no H22 C2 2.82(3) . 2_664 no H22 C18 3.04(3) . 2_665 no H24 H6B 2.59(6) . 1_565 no H24 H8B 2.33(4) . . no H24 N6 2.91(3) . 1_565 no H25 O7 2.38(3) . . no H25 C15 2.85(3) . 3_555 no H25 H4 2.40(5) . 3_554 no H25 H5 2.53(4) . 3_554 no H25 O5 2.71(3) . 3_555 no H25 C4 2.98(3) . 3_554 no H25 C5 3.03(3) . 3_554 no H25 C14 2.79(3) . 3_555 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # N2 H2N O8 0.87(4) 2.18(4) 3.012(3) 159(4) 2_665 yes N3 H3A O2 0.99(4) 2.14(4) 3.031(3) 149(3) 3_555 yes O4 H4O N1 0.97(3) 1.61(3) 2.574(2) 173(4) 2_654 yes N5 H5N O5 0.95(3) 2.10(3) 3.019(3) 163(3) . yes O5 H5O O3 0.95(3) 1.75(3) 2.590(2) 145(3) . yes N6 H6A O1 0.88(3) 2.17(3) 3.006(3) 158(3) 3_544 yes N6 H6B O6 1.00(7) 2.34(7) 3.230(4) 147(4) 3_545 yes N7 H7A N3 0.94(3) 2.17(3) 3.088(3) 165(3) 2_664 yes N7 H7B O6 0.90(3) 2.23(3) 3.016(3) 145(3) . yes O7 H7O N4 1.25(5) 1.30(5) 2.548(2) 175(6) . yes N8 H8A O3 0.83(4) 2.29(4) 3.046(3) 153(3) 1_565 yes N8 H8B N6 0.92(3) 2.25(3) 3.164(3) 172(3) 1_565 yes O8 H8O O6 1.00(4) 1.60(4) 2.557(2) 159(4) . yes C7 H7 O1 0.95(3) 2.39(3) 3.340(3) 174(2) . yes C18 H18 O4 0.92(2) 2.44(2) 2.770(3) 101.3(17) . yes C25 H25 O7 1.05(3) 2.38(3) 2.790(3) 101.9(18) . yes #===END # Attachment 'web_deposit_cif_file_1_PawelGrobelny_1289286463.cif' # CIF-file generated for datam in Pna2(1) #============================================================================== data_datam2 _database_code_depnum_ccdc_archive 'CCDC 800231' #TrackingRef 'web_deposit_cif_file_1_PawelGrobelny_1289286463.cif' _chemical_name_systematic ; ; _chemical_name_common 'Isoniazid:4-aminosalicylic acid co-crystal' _chemical_melting_point ? _chemical_formula_moiety 'C13 H14 N4 O4, C7 H7 N O3, C6 H7 N3 O' _chemical_formula_structural ? _chemical_formula_sum 'C26 H28 N8 O8' _chemical_formula_iupac ? _chemical_formula_weight 580.56 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_space_group_name_H-M 'P n a 21' _symmetry_Int_Tables_number 33 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,1/2+z 3 1/2-x,1/2+y,1/2+z 4 1/2+x,1/2-y,z _cell_length_a 21.845(2) _cell_length_b 16.5081(13) _cell_length_c 7.2355(6) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2609.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 6846 _cell_measurement_theta_min 1.9 _cell_measurement_theta_max 27.5 _cell_special_details ; ; _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.478 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 0.112 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.825 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' #=============================================================================== _exptl_special_details ; ; _diffrn_ambient_temperature 120(2) _diffrn_source_power 0.6 _diffrn_source_voltage 50.0 _diffrn_source_current 12.0 _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_source 'Sealed Tube' _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_measurement_specimen_support Fiber _diffrn_detector CCD _diffrn_measurement_device ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_detector_area_resol_mean 13.6612 _diffrn_measurement_method 'profile data from \w-scans' _diffrn_reflns_number 26990 _diffrn_reflns_av_R_equivalents 0.0459 _diffrn_reflns_av_sigmaI/netI 0.0231 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 27.47 _reflns_number_total 3233 _reflns_number_gt 3098 _reflns_threshold_expression >2\s(I) _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measurement_details ; scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 0.0000 XTD: 49.4160 2theta: 29.5413 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 120.0000 XTD: 49.4160 2theta: 29.5413 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 240.0000 XTD: 49.4160 2theta: 29.5413 ; _diffrn_orient_matrix_UB_11 0.014934 _diffrn_orient_matrix_UB_12 -0.136368 _diffrn_orient_matrix_UB_13 0.016793 _diffrn_orient_matrix_UB_21 0.060156 _diffrn_orient_matrix_UB_22 0.006836 _diffrn_orient_matrix_UB_23 0.002017 _diffrn_orient_matrix_UB_31 -0.002131 _diffrn_orient_matrix_UB_32 0.005359 _diffrn_orient_matrix_UB_33 0.045412 _diffrn_orient_matrix_type d*Trek _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement ? _computing_molecular_graphics ? _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== _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^ > 2\s(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^)+(0.0525P)^2^+0.5191P] 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 3233 _refine_ls_number_parameters 492 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0378 _refine_ls_R_factor_gt 0.0359 _refine_ls_wR_factor_ref 0.0948 _refine_ls_wR_factor_gt 0.0926 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.227 _refine_diff_density_min -0.181 _refine_diff_density_rms 0.039 #=============================================================================== loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags O2 O Uani 0.11417(7) 0.10512(9) 0.9152(3) 1.000 0.0330(5) . . O6 O Uani 0.31646(7) 0.50617(9) 0.9879(3) 1.000 0.0318(5) . . O7 O Uani 0.22096(7) 0.53679(9) 0.9013(3) 1.000 0.0315(5) . . O8 O Uani 0.39842(7) 0.61668(11) 0.9903(3) 1.000 0.0309(5) . . N4 N Uani 0.20078(8) 0.38487(10) 0.9103(3) 1.000 0.0251(5) . . N5 N Uani 0.21605(9) 0.08066(11) 0.9298(3) 1.000 0.0258(5) . . N6 N Uani 0.21048(10) -0.00552(11) 0.9276(4) 1.000 0.0321(6) . . N8 N Uani 0.33276(10) 0.89177(11) 0.9190(3) 1.000 0.0307(6) . . C7 C Uani 0.24353(9) 0.33374(13) 0.8451(3) 1.000 0.0245(6) . . C8 C Uani 0.23527(10) 0.24993(13) 0.8472(3) 1.000 0.0227(6) . . C9 C Uani 0.18118(9) 0.21900(11) 0.9174(3) 1.000 0.0210(5) . . C10 C Uani 0.13676(9) 0.27198(14) 0.9813(3) 1.000 0.0228(6) . . C11 C Uani 0.14802(9) 0.35491(14) 0.9762(3) 1.000 0.0251(6) . . C12 C Uani 0.16710(9) 0.12930(12) 0.9217(3) 1.000 0.0234(6) . . C20 C Uani 0.29262(9) 0.64352(12) 0.9187(3) 1.000 0.0219(5) . . C21 C Uani 0.35268(9) 0.67029(13) 0.9539(3) 1.000 0.0238(6) . . C22 C Uani 0.36585(10) 0.75279(14) 0.9543(3) 1.000 0.0255(6) . . C23 C Uani 0.32041(10) 0.81029(12) 0.9166(3) 1.000 0.0242(6) . . C24 C Uani 0.26122(10) 0.78284(13) 0.8711(3) 1.000 0.0232(6) . . C25 C Uani 0.24827(10) 0.70135(13) 0.8722(3) 1.000 0.0227(6) . . C26 C Uani 0.27699(10) 0.55677(13) 0.9370(3) 1.000 0.0250(6) . . O3 O Uani 0.42421(7) 0.00177(9) 0.1148(3) 1.000 0.0332(5) . . O4 O Uani 0.52183(7) 0.03584(9) 0.1699(3) 1.000 0.0319(5) . . O5 O Uani 0.34725(7) 0.11608(10) 0.0360(3) 1.000 0.0288(5) . . N7 N Uani 0.40920(10) 0.38898(12) 0.1452(4) 1.000 0.0313(6) . . C13 C Uani 0.44956(9) 0.14060(12) 0.1485(3) 1.000 0.0223(6) . . C14 C Uani 0.39154(9) 0.16880(13) 0.0922(3) 1.000 0.0231(6) . . C15 C Uani 0.37834(9) 0.25084(13) 0.0920(3) 1.000 0.0224(6) . . C16 C Uani 0.42238(9) 0.30765(12) 0.1452(3) 1.000 0.0229(6) . . C17 C Uani 0.48037(10) 0.28011(13) 0.2055(3) 1.000 0.0242(6) . . C18 C Uani 0.49290(9) 0.19822(13) 0.2053(3) 1.000 0.0226(6) . . C19 C Uani 0.46415(9) 0.05383(13) 0.1437(3) 1.000 0.0252(6) . . O1 O Uani 0.37592(7) 0.40050(10) 0.6703(3) 1.000 0.0326(5) . . N1 N Uani 0.45631(8) 0.11739(11) 0.6588(3) 1.000 0.0255(5) . . N2 N Uani 0.47762(8) 0.42133(11) 0.6517(3) 1.000 0.0311(6) . . N3 N Uani 0.47324(9) 0.50699(12) 0.6517(4) 1.000 0.0368(7) . . C1 C Uani 0.50045(10) 0.16651(14) 0.7193(3) 1.000 0.0262(6) . . C2 C Uani 0.49491(9) 0.25011(13) 0.7239(3) 1.000 0.0236(6) . . C3 C Uani 0.44013(9) 0.28407(12) 0.6621(3) 1.000 0.0221(6) . . C4 C Uani 0.39376(10) 0.23308(14) 0.6004(3) 1.000 0.0251(6) . . C5 C Uani 0.40341(10) 0.15034(14) 0.6002(4) 1.000 0.0264(6) . . C6 C Uani 0.42818(9) 0.37355(13) 0.6609(3) 1.000 0.0243(6) . . H5N H Uiso 0.2531(15) 0.0966(18) 0.947(5) 1.000 0.051(10) . . H6A H Uiso 0.193(2) -0.024(3) 0.802(7) 1.000 0.080(13) . . H6B H Uiso 0.1843(17) -0.024(2) 1.015(6) 1.000 0.050(10) . . H7 H Uiso 0.2809(11) 0.3554(15) 0.801(4) 1.000 0.024(6) . . H7O H Uiso 0.210(2) 0.470(3) 0.909(9) 1.000 0.112(17) . . H8 H Uiso 0.2644(11) 0.2182(15) 0.798(4) 1.000 0.020(6) . . H8A H Uiso 0.2986(13) 0.9269(17) 0.911(5) 1.000 0.034(7) . . H8B H Uiso 0.3678(17) 0.910(2) 0.964(6) 1.000 0.062(11) . . H8O H Uiso 0.3762(18) 0.573(2) 0.987(6) 1.000 0.068(12) . . H10 H Uiso 0.0993(13) 0.2515(17) 1.037(5) 1.000 0.034(7) . . H11 H Uiso 0.1175(12) 0.3956(15) 1.031(4) 1.000 0.024(6) . . H22 H Uiso 0.4026(14) 0.7720(18) 0.982(5) 1.000 0.039(8) . . H24 H Uiso 0.2280(14) 0.8196(18) 0.849(5) 1.000 0.044(9) . . H25 H Uiso 0.2072(12) 0.6851(14) 0.844(4) 1.000 0.025(6) . . H4O H Uiso 0.5340(17) -0.025(2) 0.159(7) 1.000 0.073(12) . . H5O H Uiso 0.3613(13) 0.0682(18) 0.058(5) 1.000 0.039(8) . . H7A H Uiso 0.4401(14) 0.4192(19) 0.154(6) 1.000 0.046(9) . . H7B H Uiso 0.3790(15) 0.4053(19) 0.076(5) 1.000 0.044(9) . . H15 H Uiso 0.3354(12) 0.2671(15) 0.058(4) 1.000 0.026(7) . . H17 H Uiso 0.5096(12) 0.3184(16) 0.239(4) 1.000 0.025(7) . . H18 H Uiso 0.5320(11) 0.1729(15) 0.253(4) 1.000 0.023(6) . . H1 H Uiso 0.5374(11) 0.1342(15) 0.762(4) 1.000 0.024(6) . . H2 H Uiso 0.5283(13) 0.2848(18) 0.762(5) 1.000 0.043(9) . . H2N H Uiso 0.5160(14) 0.4022(17) 0.630(5) 1.000 0.044(8) . . H3A H Uiso 0.4463(17) 0.521(2) 0.545(6) 1.000 0.055(10) . . H4 H Uiso 0.3554(13) 0.2582(18) 0.561(5) 1.000 0.039(8) . . H4B H Uiso 0.4538(19) 0.520(2) 0.760(7) 1.000 0.065(12) . . H5 H Uiso 0.3701(12) 0.1142(16) 0.559(4) 1.000 0.030(7) . . 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 O2 0.0207(7) 0.0267(8) 0.0515(11) 0.0018(8) -0.0015(8) -0.0056(6) O6 0.0258(8) 0.0239(7) 0.0458(10) -0.0004(7) -0.0034(8) 0.0052(6) O7 0.0238(8) 0.0206(7) 0.0500(10) 0.0019(8) -0.0057(8) -0.0017(5) O8 0.0169(7) 0.0337(9) 0.0420(10) 0.0034(8) -0.0010(7) 0.0030(6) N4 0.0242(9) 0.0214(8) 0.0296(10) 0.0009(8) -0.0031(8) -0.0028(7) N5 0.0221(9) 0.0171(8) 0.0382(11) -0.0005(9) -0.0035(9) -0.0029(7) N6 0.0325(10) 0.0184(8) 0.0453(13) -0.0003(10) -0.0013(10) -0.0027(7) N8 0.0290(10) 0.0242(9) 0.0389(11) -0.0011(9) -0.0027(10) -0.0067(8) C7 0.0189(10) 0.0251(10) 0.0295(11) 0.0012(9) 0.0007(9) -0.0029(8) C8 0.0200(10) 0.0242(11) 0.0239(12) -0.0002(9) -0.0001(8) 0.0001(8) C9 0.0205(9) 0.0204(9) 0.0221(10) -0.0006(9) -0.0035(8) -0.0026(7) C10 0.0170(9) 0.0264(10) 0.0249(11) -0.0003(9) -0.0019(9) -0.0026(8) C11 0.0216(10) 0.0258(10) 0.0280(11) -0.0016(9) -0.0032(9) 0.0006(8) C12 0.0222(10) 0.0227(9) 0.0254(10) 0.0005(9) -0.0022(9) -0.0025(8) C20 0.0189(9) 0.0233(9) 0.0234(10) -0.0016(9) 0.0015(8) -0.0007(7) C21 0.0185(9) 0.0293(10) 0.0235(11) 0.0012(9) 0.0011(8) 0.0021(8) C22 0.0182(9) 0.0316(11) 0.0266(11) 0.0000(9) -0.0003(9) -0.0055(8) C23 0.0248(10) 0.0255(10) 0.0223(10) -0.0003(9) 0.0015(9) -0.0054(8) C24 0.0203(10) 0.0225(10) 0.0269(12) -0.0010(9) 0.0003(9) -0.0010(8) C25 0.0192(10) 0.0230(10) 0.0260(12) -0.0016(9) -0.0012(9) -0.0001(7) C26 0.0231(10) 0.0227(10) 0.0292(12) -0.0030(9) 0.0007(9) 0.0022(8) O3 0.0226(7) 0.0240(7) 0.0529(12) -0.0046(8) -0.0016(8) -0.0031(6) O4 0.0204(7) 0.0235(7) 0.0519(11) -0.0002(8) -0.0020(8) 0.0007(6) O5 0.0193(7) 0.0254(8) 0.0417(10) -0.0010(7) -0.0053(7) -0.0040(6) N7 0.0253(10) 0.0238(9) 0.0449(13) 0.0007(10) -0.0043(10) 0.0008(8) C13 0.0200(9) 0.0230(10) 0.0238(10) -0.0014(9) 0.0011(9) -0.0019(8) C14 0.0185(9) 0.0271(10) 0.0238(10) -0.0007(9) 0.0013(8) -0.0043(8) C15 0.0162(9) 0.0266(11) 0.0245(11) 0.0010(9) -0.0001(8) -0.0016(8) C16 0.0225(10) 0.0242(10) 0.0221(10) -0.0003(9) 0.0024(9) 0.0006(8) C17 0.0217(10) 0.0252(11) 0.0256(11) -0.0032(9) 0.0002(9) -0.0050(8) C18 0.0181(9) 0.0270(10) 0.0227(11) -0.0018(9) 0.0003(9) -0.0017(8) C19 0.0205(9) 0.0257(10) 0.0294(11) -0.0013(10) -0.0004(9) -0.0014(8) O1 0.0204(7) 0.0296(8) 0.0477(11) 0.0040(8) 0.0048(8) 0.0035(6) N1 0.0223(8) 0.0248(8) 0.0295(10) 0.0016(9) 0.0008(8) -0.0009(7) N2 0.0204(8) 0.0221(9) 0.0508(13) 0.0015(10) 0.0040(10) 0.0009(7) N3 0.0277(9) 0.0232(9) 0.0595(16) 0.0027(11) 0.0025(12) -0.0012(7) C1 0.0205(10) 0.0294(11) 0.0286(11) 0.0034(10) -0.0004(9) 0.0014(8) C2 0.0194(9) 0.0272(11) 0.0243(11) 0.0007(9) -0.0001(8) -0.0002(8) C3 0.0181(9) 0.0273(10) 0.0208(10) 0.0012(9) 0.0028(8) -0.0003(7) C4 0.0173(9) 0.0313(11) 0.0267(11) 0.0003(10) 0.0013(9) 0.0008(8) C5 0.0208(10) 0.0278(11) 0.0307(12) -0.0021(10) -0.0004(9) -0.0017(8) C6 0.0209(9) 0.0240(10) 0.0279(11) 0.0013(10) 0.0038(9) 0.0023(8) #=============================================================================== _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; 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 O2 C12 1.224(2) . . yes O6 C26 1.256(3) . . yes O7 C26 1.294(3) . . yes O8 C21 1.361(3) . . yes O7 H7O 1.13(5) . . no O8 H8O 0.87(3) . . no O3 C19 1.242(3) . . yes O4 C19 1.308(3) . . yes O5 C14 1.363(3) . . yes O4 H4O 1.04(3) . . no O5 H5O 0.86(3) . . no O1 C6 1.227(3) . . yes N4 C7 1.344(3) . . yes N4 C11 1.342(3) . . yes N5 N6 1.428(3) . . yes N5 C12 1.339(3) . . yes N8 C23 1.372(3) . . yes N4 H7O 1.42(5) . . no N5 H5N 0.86(3) . . no N6 H6A 1.03(5) . . no N6 H6B 0.91(4) . . no N8 H8A 0.95(3) . . no N8 H8B 0.89(4) . . no N7 C16 1.373(3) . . yes N7 H7B 0.87(3) . . no N7 H7A 0.84(3) . . no N1 C5 1.346(3) . . yes N1 C1 1.334(3) . . yes N2 C6 1.339(3) . . yes N2 N3 1.417(3) . . yes N2 H2N 0.91(3) . . no N3 H3A 1.00(4) . . no N3 H4B 0.92(5) . . no C7 C8 1.395(3) . . no C8 C9 1.384(3) . . no C9 C10 1.386(3) . . no C9 C12 1.513(3) . . no C10 C11 1.391(3) . . no C20 C25 1.401(3) . . no C20 C26 1.478(3) . . no C20 C21 1.408(3) . . no C21 C22 1.392(3) . . no C22 C23 1.400(3) . . no C23 C24 1.409(3) . . no C24 C25 1.375(3) . . no C7 H7 0.95(2) . . no C8 H8 0.90(3) . . no C10 H10 0.97(3) . . no C11 H11 1.03(3) . . no C22 H22 0.89(3) . . no C24 H24 0.96(3) . . no C25 H25 0.96(3) . . no C13 C14 1.410(3) . . no C13 C19 1.468(3) . . no C13 C18 1.404(3) . . no C14 C15 1.385(3) . . no C15 C16 1.398(3) . . no C16 C17 1.415(3) . . no C17 C18 1.379(3) . . no C15 H15 1.01(3) . . no C17 H17 0.93(3) . . no C18 H18 1.01(2) . . no C1 C2 1.386(3) . . no C2 C3 1.395(3) . . no C3 C4 1.391(3) . . no C3 C6 1.500(3) . . no C4 C5 1.382(3) . . no C1 H1 1.02(2) . . no C2 H2 0.97(3) . . no C4 H4 0.98(3) . . no C5 H5 0.99(3) . . 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 C26 O7 H7O 116(2) . . . no C21 O8 H8O 97(3) . . . no C19 O4 H4O 117(2) . . . no C14 O5 H5O 106(2) . . . no C7 N4 C11 119.34(18) . . . yes N6 N5 C12 121.95(19) . . . yes C11 N4 H7O 119.3(19) . . . no C7 N4 H7O 121.4(19) . . . no C12 N5 H5N 125(2) . . . no N6 N5 H5N 113(2) . . . no H6A N6 H6B 106(4) . . . no N5 N6 H6B 112(2) . . . no N5 N6 H6A 110(3) . . . no H8A N8 H8B 120(3) . . . no C23 N8 H8B 121(2) . . . no C23 N8 H8A 116.4(17) . . . no C16 N7 H7A 114(2) . . . no H7A N7 H7B 118(3) . . . no C16 N7 H7B 118(2) . . . no C1 N1 C5 118.59(19) . . . yes N3 N2 C6 122.23(18) . . . yes C6 N2 H2N 123.2(18) . . . no N3 N2 H2N 114.1(18) . . . no N2 N3 H4B 105(2) . . . no N2 N3 H3A 105.7(19) . . . no H3A N3 H4B 110(4) . . . no N4 C7 C8 121.93(19) . . . yes C7 C8 C9 118.70(19) . . . no C8 C9 C12 122.85(18) . . . no C10 C9 C12 117.94(18) . . . no C8 C9 C10 119.18(18) . . . no C9 C10 C11 119.23(18) . . . no N4 C11 C10 121.60(19) . . . yes O2 C12 N5 124.10(19) . . . yes O2 C12 C9 120.70(18) . . . yes N5 C12 C9 115.19(17) . . . yes C25 C20 C26 121.46(18) . . . no C21 C20 C26 120.21(18) . . . no C21 C20 C25 118.30(19) . . . no O8 C21 C22 118.96(18) . . . yes O8 C21 C20 121.02(19) . . . yes C20 C21 C22 120.01(19) . . . no C21 C22 C23 121.1(2) . . . no N8 C23 C22 121.5(2) . . . yes C22 C23 C24 118.56(19) . . . no N8 C23 C24 119.9(2) . . . yes C23 C24 C25 120.1(2) . . . no C20 C25 C24 121.7(2) . . . no O6 C26 C20 120.81(19) . . . yes O7 C26 C20 116.59(18) . . . yes O6 C26 O7 122.6(2) . . . yes C8 C7 H7 119.3(15) . . . no N4 C7 H7 118.7(15) . . . no C7 C8 H8 118.9(16) . . . no C9 C8 H8 122.4(16) . . . no C11 C10 H10 120.1(17) . . . no C9 C10 H10 120.5(17) . . . no C10 C11 H11 121.3(14) . . . no N4 C11 H11 117.0(14) . . . no C21 C22 H22 122.5(19) . . . no C23 C22 H22 116.3(19) . . . no C23 C24 H24 122.0(18) . . . no C25 C24 H24 117.7(18) . . . no C20 C25 H25 120.5(14) . . . no C24 C25 H25 117.7(14) . . . no C14 C13 C18 117.84(18) . . . no C14 C13 C19 120.69(18) . . . no C18 C13 C19 121.45(18) . . . no O5 C14 C13 120.88(19) . . . yes C13 C14 C15 120.68(19) . . . no O5 C14 C15 118.44(18) . . . yes C14 C15 C16 120.84(18) . . . no C15 C16 C17 119.06(18) . . . no N7 C16 C15 120.78(19) . . . yes N7 C16 C17 120.13(19) . . . yes C16 C17 C18 119.49(19) . . . no C13 C18 C17 122.05(19) . . . no O3 C19 O4 122.94(19) . . . yes O4 C19 C13 115.29(18) . . . yes O3 C19 C13 121.77(18) . . . yes C16 C15 H15 122.0(14) . . . no C14 C15 H15 117.1(14) . . . no C16 C17 H17 118.5(16) . . . no C18 C17 H17 122.0(16) . . . no C13 C18 H18 112.9(14) . . . no C17 C18 H18 124.9(14) . . . no N1 C1 C2 123.4(2) . . . yes C1 C2 C3 117.87(19) . . . no C2 C3 C4 118.98(19) . . . no C4 C3 C6 117.87(18) . . . no C2 C3 C6 123.15(18) . . . no C3 C4 C5 119.2(2) . . . no N1 C5 C4 122.0(2) . . . yes O1 C6 C3 121.24(19) . . . yes N2 C6 C3 116.10(17) . . . yes O1 C6 N2 122.7(2) . . . yes N1 C1 H1 110.8(14) . . . no C2 C1 H1 125.8(14) . . . no C1 C2 H2 122.0(17) . . . no C3 C2 H2 120.0(17) . . . no C3 C4 H4 117.5(18) . . . no C5 C4 H4 123.4(17) . . . no N1 C5 H5 118.9(16) . . . no C4 C5 H5 119.0(16) . . . 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 N4 C7 C8 -1.3(3) . . . . no C7 N4 C11 C10 1.0(3) . . . . no N6 N5 C12 O2 1.4(4) . . . . no N6 N5 C12 C9 -177.6(2) . . . . no C1 N1 C5 C4 0.2(4) . . . . no C5 N1 C1 C2 -0.5(4) . . . . no N3 N2 C6 C3 -179.2(2) . . . . no N3 N2 C6 O1 -0.2(4) . . . . no N4 C7 C8 C9 0.5(3) . . . . no C7 C8 C9 C12 178.5(2) . . . . no C7 C8 C9 C10 0.7(3) . . . . no C10 C9 C12 N5 -154.9(2) . . . . no C12 C9 C10 C11 -178.95(19) . . . . no C8 C9 C12 O2 -151.7(2) . . . . no C8 C9 C10 C11 -1.1(3) . . . . no C10 C9 C12 O2 26.1(3) . . . . no C8 C9 C12 N5 27.3(3) . . . . no C9 C10 C11 N4 0.2(3) . . . . no C26 C20 C21 O8 5.4(3) . . . . no C26 C20 C25 C24 174.1(2) . . . . no C21 C20 C26 O6 1.6(3) . . . . no C21 C20 C25 C24 -3.9(3) . . . . no C25 C20 C26 O6 -176.4(2) . . . . no C25 C20 C26 O7 2.5(3) . . . . no C25 C20 C21 C22 4.3(3) . . . . no C21 C20 C26 O7 -179.6(2) . . . . no C26 C20 C21 C22 -173.7(2) . . . . no C25 C20 C21 O8 -176.6(2) . . . . no O8 C21 C22 C23 179.6(2) . . . . no C20 C21 C22 C23 -1.2(3) . . . . no C21 C22 C23 C24 -2.4(3) . . . . no C21 C22 C23 N8 179.2(2) . . . . no C22 C23 C24 C25 2.8(3) . . . . no N8 C23 C24 C25 -178.7(2) . . . . no C23 C24 C25 C20 0.3(3) . . . . no C18 C13 C14 C15 0.5(3) . . . . no C19 C13 C18 C17 178.1(2) . . . . no C19 C13 C14 C15 -178.2(2) . . . . no C14 C13 C18 C17 -0.6(3) . . . . no C18 C13 C19 O3 171.4(2) . . . . no C18 C13 C19 O4 -9.3(3) . . . . no C19 C13 C14 O5 1.5(3) . . . . no C14 C13 C19 O4 169.4(2) . . . . no C18 C13 C14 O5 -179.8(2) . . . . no C14 C13 C19 O3 -9.9(3) . . . . no C13 C14 C15 C16 0.8(3) . . . . no O5 C14 C15 C16 -178.9(2) . . . . no C14 C15 C16 N7 -179.9(2) . . . . no C14 C15 C16 C17 -2.1(3) . . . . no C15 C16 C17 C18 2.0(3) . . . . no N7 C16 C17 C18 179.8(2) . . . . no C16 C17 C18 C13 -0.6(3) . . . . no N1 C1 C2 C3 0.1(3) . . . . no C1 C2 C3 C4 0.4(3) . . . . no C1 C2 C3 C6 179.6(2) . . . . no C2 C3 C6 N2 25.3(3) . . . . no C4 C3 C6 O1 25.4(3) . . . . no C4 C3 C6 N2 -155.5(2) . . . . no C2 C3 C6 O1 -153.8(2) . . . . no C2 C3 C4 C5 -0.7(3) . . . . no C6 C3 C4 C5 -179.9(2) . . . . no C3 C4 C5 N1 0.3(4) . . . . 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 O1 N6 3.009(3) . 3_554 no O1 C7 3.343(3) . . no O1 O6 3.164(3) . . no O1 N3 2.762(3) . . no O2 N6 2.788(3) . . no O2 N3 3.033(3) . 3_545 no O2 O8 3.093(3) . 3_544 no O3 C1 3.316(3) . 2_654 no O3 O5 2.591(2) . . no O3 N8 3.049(3) . 1_544 no O4 C1 3.395(3) . 2_654 no O4 N1 2.576(2) . 2_654 no O5 N5 3.024(3) . 1_554 no O5 O3 2.591(2) . . no O6 O1 3.164(3) . . no O6 N7 3.024(3) . 1_556 no O6 N6 3.241(4) . 3_555 no O6 O8 2.556(2) . . no O8 O2 3.093(3) . 3_555 no O8 O6 2.556(2) . . no O8 N2 3.015(2) . 2_665 no O1 H7 2.40(2) . . no O1 H3A 2.67(4) . . no O1 H4 2.52(3) . . no O1 H4B 2.69(4) . . no O1 H6B 2.13(4) . 3_554 no O2 H2 2.84(3) . 4_455 no O2 H6B 2.72(4) . . no O2 H6A 2.86(5) . . no O2 H3A 2.13(4) . 3_545 no O2 H10 2.59(3) . . no O3 H1 2.62(3) . 2_654 no O3 H8B 2.24(4) . 1_544 no O3 H5O 1.81(3) . . no O4 H11 2.58(3) . 4_554 no O4 H18 2.35(3) . . no O5 H5N 2.18(3) . 1_554 no O5 H25 2.77(3) . 3_544 no O6 H7B 2.25(3) . 1_556 no O6 H8O 1.71(4) . . no O6 H6A 2.34(5) . 3_555 no O7 H25 2.50(2) . . no O7 H5 2.63(3) . 3_555 no O8 H17 2.91(3) . 2_665 no O8 H4B 2.61(4) . . no O8 H2N 2.15(3) . 2_665 no N1 C19 3.320(3) . 2_655 no N1 O4 2.576(2) . 2_655 no N2 O8 3.015(2) . 2_664 no N3 N7 3.090(3) . 2_665 no N3 O1 2.762(3) . . no N3 O2 3.033(3) . 3_554 no N5 O5 3.024(3) . 1_556 no N6 N8 3.165(3) . 1_545 no N6 O6 3.241(4) . 3_544 no N6 O1 3.009(3) . 3_545 no N6 O2 2.788(3) . . no N7 O6 3.024(3) . 1_554 no N7 N3 3.090(3) . 2_664 no N8 O3 3.049(3) . 1_566 no N8 N6 3.165(3) . 1_565 no N8 C11 3.288(3) . 3_554 no N1 H4O 1.54(3) . 2_655 no N2 H2 2.64(3) . . no N3 H7A 2.25(3) . 2_665 no N5 H8 2.68(3) . . no N6 H8A 2.23(3) . 1_545 no N7 H6A 2.89(5) . 3_554 no C1 C14 3.597(3) . 1_556 no C1 O4 3.395(3) . 2_655 no C1 C18 3.559(3) . 1_556 no C1 O3 3.316(3) . 2_655 no C1 C13 3.326(3) . 1_556 no C2 C17 3.534(3) . 1_556 no C2 C18 3.587(3) . 1_556 no C2 C16 3.564(3) . 1_556 no C3 C17 3.419(3) . . no C3 C15 3.435(3) . 1_556 no C3 C16 3.538(3) . 1_556 no C4 C15 3.585(3) . 1_556 no C4 C17 3.514(3) . . no C4 C25 3.554(3) . 3_544 no C4 C16 3.571(3) . . no C5 C14 3.582(4) . 1_556 no C5 C13 3.424(4) . . no C5 C18 3.551(3) . . no C7 C24 3.533(3) . 3_544 no C7 C23 3.423(3) . 3_544 no C7 O1 3.343(3) . . no C8 C24 3.488(3) . 3_544 no C8 C23 3.490(3) . 3_544 no C8 C15 3.592(3) . 1_556 no C8 C25 3.548(3) . 3_544 no C9 C21 3.527(3) . 3_544 no C9 C22 3.549(3) . 3_544 no C10 C18 3.570(3) . 4_456 no C10 C23 3.346(3) . 3_545 no C10 C24 3.599(3) . 3_545 no C10 C22 3.438(3) . 3_545 no C11 C23 3.343(3) . 3_545 no C11 N8 3.288(3) . 3_545 no C12 C21 3.479(3) . 3_544 no C13 C5 3.424(4) . . no C13 C1 3.326(3) . 1_554 no C14 C1 3.597(3) . 1_554 no C14 C5 3.582(4) . 1_554 no C15 C8 3.592(3) . 1_554 no C15 C4 3.585(3) . 1_554 no C15 C25 3.525(3) . 3_544 no C15 C3 3.435(3) . 1_554 no C16 C4 3.571(3) . . no C16 C2 3.564(3) . 1_554 no C16 C3 3.538(3) . 1_554 no C17 C4 3.514(3) . . no C17 C2 3.534(3) . 1_554 no C17 C3 3.419(3) . . no C18 C10 3.570(3) . 4_554 no C18 C5 3.551(3) . . no C18 C2 3.587(3) . 1_554 no C18 C1 3.559(3) . 1_554 no C19 N1 3.320(3) . 2_654 no C21 C12 3.479(3) . 3_555 no C21 C9 3.527(3) . 3_555 no C22 C9 3.549(3) . 3_555 no C22 C10 3.438(3) . 3_554 no C23 C10 3.346(3) . 3_554 no C23 C8 3.490(3) . 3_555 no C23 C7 3.423(3) . 3_555 no C23 C11 3.343(3) . 3_554 no C24 C10 3.599(3) . 3_554 no C24 C8 3.488(3) . 3_555 no C24 C7 3.533(3) . 3_555 no C25 C4 3.554(3) . 3_555 no C25 C15 3.525(3) . 3_555 no C25 C8 3.548(3) . 3_555 no C1 H22 2.91(3) . 2_664 no C1 H4O 2.49(3) . 2_655 no C2 H22 2.87(3) . 2_664 no C2 H2N 2.64(3) . . no C4 H25 2.99(3) . 3_544 no C5 H4O 2.52(4) . 2_655 no C5 H25 3.10(3) . 3_544 no C7 H15 2.76(3) . 1_556 no C8 H15 2.68(3) . 1_556 no C8 H5N 2.66(3) . . no C10 H2 3.00(3) . 4_455 no C11 H1 2.88(3) . 4_455 no C14 H25 2.84(3) . 3_544 no C15 H25 2.83(3) . 3_544 no C17 H10 2.92(3) . 4_554 no C18 H10 2.75(3) . 4_554 no C18 H22 3.08(3) . 2_664 no C19 H5O 2.34(3) . . no C22 H18 2.93(3) . 2_665 no C24 H4 2.92(3) . 3_555 no C25 H4 2.81(3) . 3_555 no C26 H8O 2.21(4) . . no C26 H6A 3.03(5) . 3_555 no H1 C11 2.88(3) . 4_555 no H1 O3 2.62(3) . 2_655 no H1 H4O 2.50(4) . 2_655 no H2 N2 2.64(3) . . no H2 O2 2.84(3) . 4_555 no H2 C10 3.00(3) . 4_555 no H2 H10 2.59(5) . 4_555 no H2 H2N 2.18(4) . . no H2N O8 2.15(3) . 2_664 no H2N C2 2.64(3) . . no H2N H2 2.18(4) . . no H3A O1 2.67(4) . . no H3A O2 2.13(4) . 3_554 no H4 C24 2.92(3) . 3_544 no H4 O1 2.52(3) . . no H4 H24 2.59(5) . 3_544 no H4 C25 2.81(3) . 3_544 no H4 H25 2.41(4) . 3_544 no H4B O8 2.61(4) . . no H4B H8O 2.52(6) . . no H4B O1 2.69(4) . . no H4O C5 2.52(4) . 2_654 no H4O N1 1.54(3) . 2_654 no H4O C1 2.49(3) . 2_654 no H4O H1 2.50(4) . 2_654 no H5 H25 2.58(4) . 3_544 no H5 O7 2.63(3) . 3_544 no H5N H5O 2.54(4) . 1_556 no H5N H8 2.29(4) . . no H5N C8 2.66(3) . . no H5N O5 2.18(3) . 1_556 no H5O O3 1.81(3) . . no H5O C19 2.34(3) . . no H5O H5N 2.54(4) . 1_554 no H6A O2 2.86(5) . . no H6A H8A 2.57(5) . 1_545 no H6A N7 2.89(5) . 3_545 no H6A C26 3.03(5) . 3_544 no H6A O6 2.34(5) . 3_544 no H6A H7B 2.55(6) . 3_545 no H6B O1 2.13(4) . 3_545 no H6B O2 2.72(4) . . no H7 O1 2.40(2) . . no H7A H17 2.34(4) . . no H7A N3 2.25(3) . 2_664 no H7B H6A 2.55(6) . 3_554 no H7B H15 2.48(4) . . no H7B O6 2.25(3) . 1_554 no H8 H15 2.57(4) . 1_556 no H8 H5N 2.29(4) . . no H8 N5 2.68(3) . . no H8A H6A 2.57(5) . 1_565 no H8A N6 2.23(3) . 1_565 no H8A H24 2.39(4) . . no H8B H22 2.41(4) . . no H8B O3 2.24(4) . 1_566 no H8O H4B 2.52(6) . . no H8O O6 1.71(4) . . no H8O C26 2.21(4) . . no H10 H2 2.59(5) . 4_455 no H10 C18 2.75(3) . 4_456 no H10 O2 2.59(3) . . no H10 H18 2.48(4) . 4_456 no H10 C17 2.92(3) . 4_456 no H11 O4 2.58(3) . 4_456 no H15 C8 2.68(3) . 1_554 no H15 H7B 2.48(4) . . no H15 C7 2.76(3) . 1_554 no H15 H8 2.57(4) . 1_554 no H17 H7A 2.34(4) . . no H17 O8 2.91(3) . 2_664 no H18 H22 2.37(4) . 2_664 no H18 H10 2.48(4) . 4_554 no H18 O4 2.35(3) . . no H18 C22 2.93(3) . 2_664 no H22 C18 3.08(3) . 2_665 no H22 H18 2.37(4) . 2_665 no H22 H8B 2.41(4) . . no H22 C1 2.91(3) . 2_665 no H22 C2 2.87(3) . 2_665 no H24 H8A 2.39(4) . . no H24 H4 2.59(5) . 3_555 no H25 O7 2.50(2) . . no H25 C14 2.84(3) . 3_555 no H25 C15 2.83(3) . 3_555 no H25 H4 2.41(4) . 3_555 no H25 H5 2.58(4) . 3_555 no H25 O5 2.77(3) . 3_555 no H25 C4 2.99(3) . 3_555 no H25 C5 3.10(3) . 3_555 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # N2 H2N O8 0.91(3) 2.15(3) 3.015(2) 159(3) 2_664 yes N3 H3A O2 1.00(4) 2.13(4) 3.033(3) 149(3) 3_554 yes O4 H4O N1 1.04(3) 1.54(3) 2.576(2) 172(3) 2_654 yes N5 H5N O5 0.86(3) 2.18(3) 3.024(3) 167(3) 1_556 yes O5 H5O O3 0.86(3) 1.81(3) 2.591(2) 150(3) . yes N6 H6A O6 1.03(5) 2.34(5) 3.241(4) 146(4) 3_544 yes N6 H6B O1 0.91(4) 2.13(4) 3.009(3) 163(3) 3_545 yes N7 H7A N3 0.84(3) 2.25(3) 3.090(3) 174(4) 2_664 yes N7 H7B O6 0.87(3) 2.25(3) 3.024(3) 149(3) 1_554 yes O7 H7O N4 1.13(5) 1.42(5) 2.547(2) 175(5) . yes N8 H8A N6 0.95(3) 2.23(3) 3.165(3) 170(3) 1_565 yes N8 H8B O3 0.89(4) 2.24(4) 3.049(3) 153(3) 1_566 yes O8 H8O O6 0.87(3) 1.71(4) 2.556(2) 164(4) . yes C7 H7 O1 0.95(2) 2.40(2) 3.343(3) 175(2) . yes C11 H11 O4 1.03(3) 2.58(3) 3.580(3) 165(2) 4_456 yes C18 H18 O4 1.01(2) 2.35(3) 2.766(3) 103.3(17) . yes # Attachment '3092_web_deposit_cif_file_2_PawelGrobelny_1289286463.cif' # CIF-file generated for datam in Pna2(1) data_datam3 _database_code_depnum_ccdc_archive 'CCDC 800232' #TrackingRef '3092_web_deposit_cif_file_2_PawelGrobelny_1289286463.cif' _chemical_name_systematic ; ; _chemical_name_common 'Isoniazid:4-aminosalicylic acid co-crystal' _chemical_melting_point ? _chemical_formula_moiety 'C13 H14 N4 O4, C7 H7 N O3, C6 H7 N3 O' _chemical_formula_structural ? _chemical_formula_sum 'C26 H28 N8 O8' _chemical_formula_iupac ? _chemical_formula_weight 580.56 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_space_group_name_H-M 'P n a 21' _symmetry_Int_Tables_number 33 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,1/2+z 3 1/2-x,1/2+y,1/2+z 4 1/2+x,1/2-y,z _cell_length_a 21.859(2) _cell_length_b 16.5084(14) _cell_length_c 7.2459(6) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2614.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 140(2) _cell_measurement_reflns_used 6885 _cell_measurement_theta_min 1.9 _cell_measurement_theta_max 27.5 _cell_special_details ; ; _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.475 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 0.112 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.844 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' #=============================================================================== _exptl_special_details ; ; _diffrn_ambient_temperature 140 _diffrn_source_power 0.6 _diffrn_source_voltage 50.0 _diffrn_source_current 12.0 _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_source 'Sealed Tube' _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_measurement_specimen_support Fiber _diffrn_detector CCD _diffrn_measurement_device ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_detector_area_resol_mean 13.6612 _diffrn_measurement_method 'profile data from \w-scans' _diffrn_reflns_number 27058 _diffrn_reflns_av_R_equivalents 0.0504 _diffrn_reflns_av_sigmaI/netI 0.0229 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 27.47 _reflns_number_total 3240 _reflns_number_gt 3116 _reflns_threshold_expression >2\s(I) _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measurement_details ; scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 0.0000 XTD: 49.4168 2theta: 29.5585 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 120.0000 XTD: 49.4168 2theta: 29.5585 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 240.0000 XTD: 49.4168 2theta: 29.5585 ; _diffrn_orient_matrix_UB_11 0.014947 _diffrn_orient_matrix_UB_12 -0.136173 _diffrn_orient_matrix_UB_13 0.016734 _diffrn_orient_matrix_UB_21 0.060154 _diffrn_orient_matrix_UB_22 0.006848 _diffrn_orient_matrix_UB_23 0.001993 _diffrn_orient_matrix_UB_31 -0.002112 _diffrn_orient_matrix_UB_32 0.005346 _diffrn_orient_matrix_UB_33 0.045386 _diffrn_orient_matrix_type d*Trek _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement ? _computing_molecular_graphics ? _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== _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^ > 2\s(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^)+(0.0707P)^2^+0.3475P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3240 _refine_ls_number_parameters 492 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0419 _refine_ls_R_factor_gt 0.0384 _refine_ls_wR_factor_ref 0.1144 _refine_ls_wR_factor_gt 0.1047 _refine_ls_goodness_of_fit_ref 1.138 _refine_ls_restrained_S_all 1.137 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.237 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.059 #=============================================================================== loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags O2 O Uani 0.11406(8) 0.10522(10) 0.5845(3) 1.000 0.0357(6) . . O6 O Uani 0.31658(8) 0.50655(11) 0.5131(3) 1.000 0.0349(5) . . O7 O Uani 0.22096(8) 0.53710(10) 0.5990(3) 1.000 0.0340(5) . . O8 O Uani 0.39842(8) 0.61692(12) 0.5098(3) 1.000 0.0336(5) . . N4 N Uani 0.20085(9) 0.38484(12) 0.5897(3) 1.000 0.0281(6) . . N5 N Uani 0.21585(9) 0.08093(12) 0.5701(3) 1.000 0.0285(6) . . N6 N Uani 0.21031(11) -0.00519(12) 0.5717(4) 1.000 0.0347(7) . . N8 N Uani 0.33264(11) 0.89180(13) 0.5815(4) 1.000 0.0333(6) . . C7 C Uani 0.24333(10) 0.33381(15) 0.6545(4) 1.000 0.0263(6) . . C8 C Uani 0.23523(10) 0.25010(14) 0.6524(4) 1.000 0.0246(7) . . C9 C Uani 0.18101(10) 0.21902(12) 0.5825(3) 1.000 0.0223(6) . . C10 C Uani 0.13680(10) 0.27213(15) 0.5186(3) 1.000 0.0244(6) . . C11 C Uani 0.14818(10) 0.35511(15) 0.5238(4) 1.000 0.0268(7) . . C12 C Uani 0.16728(10) 0.12941(13) 0.5784(4) 1.000 0.0251(6) . . C20 C Uani 0.29256(10) 0.64346(13) 0.5820(3) 1.000 0.0232(6) . . C21 C Uani 0.35261(10) 0.67089(15) 0.5459(3) 1.000 0.0255(6) . . C22 C Uani 0.36584(11) 0.75298(15) 0.5456(4) 1.000 0.0268(7) . . C23 C Uani 0.32030(11) 0.81061(14) 0.5832(4) 1.000 0.0259(6) . . C24 C Uani 0.26107(11) 0.78310(14) 0.6286(4) 1.000 0.0259(7) . . C25 C Uani 0.24844(10) 0.70149(14) 0.6275(3) 1.000 0.0242(6) . . C26 C Uani 0.27718(11) 0.55697(13) 0.5631(3) 1.000 0.0262(6) . . O3 O Uani 0.42417(8) 0.00191(10) 0.3856(3) 1.000 0.0360(6) . . O4 O Uani 0.52158(8) 0.03619(10) 0.3298(4) 1.000 0.0344(5) . . O5 O Uani 0.34715(7) 0.11620(11) 0.4637(3) 1.000 0.0313(5) . . N7 N Uani 0.40900(10) 0.38936(13) 0.3549(4) 1.000 0.0341(7) . . C13 C Uani 0.44933(10) 0.14074(14) 0.3519(3) 1.000 0.0239(6) . . C14 C Uani 0.39152(10) 0.16885(14) 0.4076(3) 1.000 0.0243(6) . . C15 C Uani 0.37832(10) 0.25103(14) 0.4083(3) 1.000 0.0248(7) . . C16 C Uani 0.42233(10) 0.30792(13) 0.3554(4) 1.000 0.0251(6) . . C17 C Uani 0.48015(11) 0.28022(14) 0.2948(3) 1.000 0.0257(6) . . C18 C Uani 0.49277(10) 0.19858(14) 0.2949(3) 1.000 0.0242(6) . . C19 C Uani 0.46406(10) 0.05388(14) 0.3560(4) 1.000 0.0278(6) . . O1 O Uani 0.37595(8) 0.40008(11) 0.8303(3) 1.000 0.0352(6) . . N1 N Uani 0.45641(9) 0.11697(12) 0.8411(3) 1.000 0.0276(6) . . N2 N Uani 0.47767(9) 0.42123(12) 0.8492(4) 1.000 0.0335(7) . . N3 N Uani 0.47334(10) 0.50661(13) 0.8483(5) 1.000 0.0399(8) . . C1 C Uani 0.50068(11) 0.16651(15) 0.7801(4) 1.000 0.0281(7) . . C2 C Uani 0.49489(10) 0.24987(14) 0.7760(4) 1.000 0.0250(7) . . C3 C Uani 0.44018(10) 0.28380(13) 0.8382(3) 1.000 0.0233(6) . . C4 C Uani 0.39399(11) 0.23278(16) 0.8992(4) 1.000 0.0269(6) . . C5 C Uani 0.40373(11) 0.14974(15) 0.8991(4) 1.000 0.0284(7) . . C6 C Uani 0.42809(10) 0.37331(14) 0.8391(4) 1.000 0.0262(6) . . H5N H Uiso 0.2532(16) 0.0979(18) 0.549(6) 1.000 0.043(9) . . H6A H Uiso 0.199(3) -0.028(3) 0.696(10) 1.000 0.11(2) . . H6B H Uiso 0.1839(16) -0.021(2) 0.485(5) 1.000 0.036(9) . . H7 H Uiso 0.2806(13) 0.3572(17) 0.692(5) 1.000 0.030(7) . . H7O H Uiso 0.212(2) 0.465(3) 0.598(9) 1.000 0.088(15) . . H8 H Uiso 0.2668(15) 0.2159(19) 0.709(5) 1.000 0.038(9) . . H8A H Uiso 0.3642(17) 0.910(2) 0.539(5) 1.000 0.041(9) . . H8B H Uiso 0.2999(15) 0.9248(19) 0.583(5) 1.000 0.032(8) . . H8O H Uiso 0.373(2) 0.565(3) 0.512(7) 1.000 0.076(14) . . H10 H Uiso 0.0991(15) 0.252(2) 0.461(5) 1.000 0.039(9) . . H11 H Uiso 0.1210(12) 0.3962(16) 0.469(4) 1.000 0.021(6) . . H22 H Uiso 0.4030(15) 0.7749(19) 0.516(5) 1.000 0.038(9) . . H24 H Uiso 0.2294(15) 0.825(2) 0.649(5) 1.000 0.043(9) . . H25 H Uiso 0.2067(15) 0.6774(19) 0.658(5) 1.000 0.046(9) . . H4O H Uiso 0.5332(19) -0.016(3) 0.333(8) 1.000 0.070(13) . . H5O H Uiso 0.3597(16) 0.065(2) 0.446(6) 1.000 0.047(10) . . H7A H Uiso 0.3772(16) 0.405(2) 0.426(5) 1.000 0.037(9) . . H7B H Uiso 0.4429(16) 0.427(2) 0.340(6) 1.000 0.052(10) . . H15A H Uiso 0.3349(14) 0.2653(18) 0.441(5) 1.000 0.032(8) . . H17 H Uiso 0.5104(14) 0.3165(18) 0.260(5) 1.000 0.028(7) . . H18 H Uiso 0.5303(11) 0.1802(14) 0.251(4) 1.000 0.012(6) . . H1 H Uiso 0.5370(14) 0.1339(19) 0.741(5) 1.000 0.036(8) . . H2 H Uiso 0.5247(15) 0.2789(19) 0.740(5) 1.000 0.036(8) . . H2N H Uiso 0.5149(15) 0.404(2) 0.868(6) 1.000 0.043(9) . . H3A H Uiso 0.452(2) 0.516(2) 0.747(7) 1.000 0.053(12) . . H3B H Uiso 0.4445(19) 0.520(3) 0.952(7) 1.000 0.056(11) . . H4 H Uiso 0.3553(14) 0.254(2) 0.939(5) 1.000 0.037(9) . . H5 H Uiso 0.3720(15) 0.1108(19) 0.939(5) 1.000 0.037(8) . . 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 O2 0.0220(8) 0.0293(9) 0.0558(12) -0.0030(9) 0.0019(9) -0.0066(7) O6 0.0273(9) 0.0269(8) 0.0505(11) 0.0002(8) 0.0039(9) 0.0066(7) O7 0.0255(8) 0.0222(8) 0.0543(12) -0.0025(9) 0.0059(9) -0.0024(6) O8 0.0191(8) 0.0348(9) 0.0470(11) -0.0037(9) 0.0019(8) 0.0033(7) N4 0.0265(10) 0.0240(9) 0.0338(11) -0.0016(9) 0.0040(9) -0.0026(7) N5 0.0227(10) 0.0194(9) 0.0434(12) 0.0007(9) 0.0046(9) -0.0024(7) N6 0.0359(11) 0.0188(9) 0.0495(15) -0.0012(10) 0.0013(12) -0.0022(8) N8 0.0301(11) 0.0278(10) 0.0421(12) 0.0025(10) 0.0020(11) -0.0081(9) C7 0.0201(10) 0.0273(11) 0.0316(12) -0.0021(10) -0.0001(9) -0.0035(8) C8 0.0213(10) 0.0253(12) 0.0271(13) -0.0001(9) 0.0002(9) -0.0020(9) C9 0.0210(10) 0.0220(10) 0.0240(10) 0.0009(9) 0.0040(9) -0.0037(8) C10 0.0180(10) 0.0271(11) 0.0282(12) 0.0007(9) 0.0023(9) -0.0029(8) C11 0.0230(11) 0.0257(11) 0.0318(12) 0.0006(10) 0.0029(10) 0.0021(9) C12 0.0240(11) 0.0226(10) 0.0288(11) 0.0003(10) 0.0030(10) -0.0025(8) C20 0.0190(10) 0.0243(10) 0.0264(11) 0.0002(9) -0.0019(9) -0.0011(8) C21 0.0190(10) 0.0330(12) 0.0244(11) -0.0009(10) -0.0005(9) 0.0036(8) C22 0.0199(10) 0.0331(12) 0.0275(12) -0.0015(10) 0.0001(9) -0.0067(9) C23 0.0259(11) 0.0285(11) 0.0233(10) -0.0007(10) -0.0011(10) -0.0056(9) C24 0.0221(10) 0.0243(11) 0.0312(13) 0.0009(10) 0.0008(10) -0.0008(9) C25 0.0201(10) 0.0251(10) 0.0275(13) 0.0014(9) 0.0002(9) -0.0008(8) C26 0.0243(11) 0.0236(10) 0.0307(12) 0.0026(10) -0.0008(10) 0.0011(8) O3 0.0254(8) 0.0247(8) 0.0578(13) 0.0050(9) 0.0025(9) -0.0032(6) O4 0.0219(7) 0.0232(8) 0.0582(12) 0.0005(9) 0.0025(9) 0.0005(6) O5 0.0196(7) 0.0288(9) 0.0455(10) 0.0010(8) 0.0054(8) -0.0054(6) N7 0.0296(11) 0.0241(10) 0.0487(14) 0.0007(10) 0.0057(11) 0.0018(8) C13 0.0212(10) 0.0243(10) 0.0261(11) 0.0007(9) -0.0008(9) -0.0029(8) C14 0.0200(10) 0.0272(11) 0.0258(11) 0.0013(9) -0.0009(9) -0.0044(8) C15 0.0182(10) 0.0296(12) 0.0266(12) -0.0016(10) 0.0003(9) -0.0003(8) C16 0.0254(11) 0.0252(10) 0.0248(11) -0.0006(10) -0.0016(10) -0.0003(8) C17 0.0225(10) 0.0269(11) 0.0276(12) 0.0032(10) 0.0004(9) -0.0046(9) C18 0.0184(10) 0.0295(11) 0.0248(12) 0.0009(10) 0.0020(9) -0.0018(8) C19 0.0236(10) 0.0265(11) 0.0333(12) 0.0022(10) -0.0002(10) -0.0024(8) O1 0.0217(8) 0.0319(9) 0.0519(12) -0.0048(9) -0.0052(9) 0.0037(6) N1 0.0250(9) 0.0252(9) 0.0325(11) -0.0015(9) -0.0008(9) -0.0014(7) N2 0.0214(9) 0.0233(9) 0.0557(15) -0.0001(11) -0.0044(10) 0.0009(7) N3 0.0281(10) 0.0236(10) 0.0680(18) -0.0012(12) -0.0035(13) -0.0007(8) C1 0.0220(10) 0.0314(12) 0.0309(12) -0.0023(10) 0.0013(10) -0.0001(9) C2 0.0201(10) 0.0292(12) 0.0258(12) 0.0000(9) 0.0017(9) -0.0019(9) C3 0.0192(10) 0.0274(11) 0.0234(10) -0.0020(9) -0.0029(9) 0.0003(8) C4 0.0193(10) 0.0332(12) 0.0282(11) -0.0008(10) 0.0005(9) -0.0003(9) C5 0.0224(11) 0.0294(11) 0.0335(13) 0.0026(10) -0.0001(10) -0.0018(9) C6 0.0213(10) 0.0269(11) 0.0304(12) -0.0032(11) -0.0038(10) 0.0027(8) #=============================================================================== _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; 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 O2 C12 1.231(3) . . yes O6 C26 1.251(3) . . yes O7 C26 1.298(3) . . yes O8 C21 1.366(3) . . yes O7 H7O 1.21(5) . . no O8 H8O 1.02(5) . . no O3 C19 1.242(3) . . yes O4 C19 1.305(3) . . yes O5 C14 1.364(3) . . yes O4 H4O 0.90(5) . . no O5 H5O 0.90(3) . . no O1 C6 1.224(3) . . yes N4 C7 1.339(3) . . yes N4 C11 1.340(3) . . yes N5 N6 1.427(3) . . yes N5 C12 1.331(3) . . yes N8 C23 1.367(3) . . yes N4 H7O 1.35(5) . . no N5 H5N 0.88(3) . . no N6 H6A 1.01(7) . . no N6 H6B 0.89(3) . . no N8 H8A 0.81(4) . . no N8 H8B 0.90(3) . . no N7 C16 1.376(3) . . yes N7 H7B 0.97(3) . . no N7 H7A 0.90(4) . . no N1 C5 1.340(3) . . yes N1 C1 1.342(3) . . yes N2 C6 1.344(3) . . yes N2 N3 1.413(3) . . yes N2 H2N 0.87(3) . . no N3 H3A 0.88(5) . . no N3 H3B 1.01(5) . . no C7 C8 1.393(3) . . no C8 C9 1.387(3) . . no C9 C10 1.385(3) . . no C9 C12 1.510(3) . . no C10 C11 1.393(3) . . no C20 C25 1.399(3) . . no C20 C26 1.473(3) . . no C20 C21 1.413(3) . . no C21 C22 1.386(3) . . no C22 C23 1.404(3) . . no C23 C24 1.411(3) . . no C24 C25 1.375(3) . . no C7 H7 0.94(3) . . no C8 H8 0.98(3) . . no C10 H10 0.98(3) . . no C11 H11 0.99(3) . . no C22 H22 0.92(3) . . no C24 H24 0.99(3) . . no C25 H25 1.02(3) . . no C13 C14 1.405(3) . . no C13 C19 1.470(3) . . no C13 C18 1.409(3) . . no C14 C15 1.387(3) . . no C15 C16 1.398(3) . . no C16 C17 1.414(3) . . no C17 C18 1.376(3) . . no C15 H15A 1.01(3) . . no C17 H17 0.93(3) . . no C18 H18 0.93(2) . . no C1 C2 1.382(3) . . no C2 C3 1.395(3) . . no C3 C4 1.387(3) . . no C3 C6 1.501(3) . . no C4 C5 1.387(4) . . no C1 H1 1.00(3) . . no C2 H2 0.85(3) . . no C4 H4 0.96(3) . . no C5 H5 0.99(3) . . 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 C26 O7 H7O 114(2) . . . no C21 O8 H8O 98(3) . . . no C19 O4 H4O 119(3) . . . no C14 O5 H5O 110(2) . . . no C7 N4 C11 119.4(2) . . . yes N6 N5 C12 122.1(2) . . . yes C11 N4 H7O 122(2) . . . no C7 N4 H7O 119(2) . . . no C12 N5 H5N 124(2) . . . no N6 N5 H5N 114(2) . . . no H6A N6 H6B 111(4) . . . no N5 N6 H6B 110(2) . . . no N5 N6 H6A 114(3) . . . no H8A N8 H8B 117(3) . . . no C23 N8 H8B 116(2) . . . no C23 N8 H8A 122(2) . . . no C16 N7 H7A 116(2) . . . no H7A N7 H7B 118(3) . . . no C16 N7 H7B 118(2) . . . no C1 N1 C5 118.5(2) . . . yes N3 N2 C6 122.21(19) . . . yes C6 N2 H2N 125(2) . . . no N3 N2 H2N 113(2) . . . no N2 N3 H3B 105(3) . . . no N2 N3 H3A 102(2) . . . no H3A N3 H3B 105(4) . . . no N4 C7 C8 122.2(2) . . . yes C7 C8 C9 118.7(2) . . . no C8 C9 C12 122.6(2) . . . no C10 C9 C12 118.4(2) . . . no C8 C9 C10 119.0(2) . . . no C9 C10 C11 119.3(2) . . . no N4 C11 C10 121.6(2) . . . yes O2 C12 N5 124.1(2) . . . yes O2 C12 C9 120.3(2) . . . yes N5 C12 C9 115.57(19) . . . yes C25 C20 C26 121.9(2) . . . no C21 C20 C26 120.4(2) . . . no C21 C20 C25 117.7(2) . . . no O8 C21 C22 119.0(2) . . . yes O8 C21 C20 120.5(2) . . . yes C20 C21 C22 120.5(2) . . . no C21 C22 C23 121.0(2) . . . no N8 C23 C22 121.5(2) . . . yes C22 C23 C24 118.6(2) . . . no N8 C23 C24 119.9(2) . . . yes C23 C24 C25 119.9(2) . . . no C20 C25 C24 122.3(2) . . . no O6 C26 C20 121.0(2) . . . yes O7 C26 C20 116.3(2) . . . yes O6 C26 O7 122.8(2) . . . yes C8 C7 H7 121.3(17) . . . no N4 C7 H7 116.3(17) . . . no C7 C8 H8 118.5(19) . . . no C9 C8 H8 122.7(19) . . . no C11 C10 H10 120(2) . . . no C9 C10 H10 121(2) . . . no C10 C11 H11 124.0(16) . . . no N4 C11 H11 114.2(16) . . . no C21 C22 H22 125(2) . . . no C23 C22 H22 114(2) . . . no C23 C24 H24 116.9(19) . . . no C25 C24 H24 123.0(19) . . . no C20 C25 H25 113.6(18) . . . no C24 C25 H25 124.1(18) . . . no C14 C13 C18 117.8(2) . . . no C14 C13 C19 120.9(2) . . . no C18 C13 C19 121.3(2) . . . no O5 C14 C13 121.0(2) . . . yes C13 C14 C15 120.7(2) . . . no O5 C14 C15 118.3(2) . . . yes C14 C15 C16 120.9(2) . . . no C15 C16 C17 118.9(2) . . . no N7 C16 C15 120.8(2) . . . yes N7 C16 C17 120.3(2) . . . yes C16 C17 C18 119.7(2) . . . no C13 C18 C17 121.9(2) . . . no O3 C19 O4 123.2(2) . . . yes O4 C19 C13 115.3(2) . . . yes O3 C19 C13 121.6(2) . . . yes C16 C15 H15A 123.8(17) . . . no C14 C15 H15A 115.2(17) . . . no C16 C17 H17 120.9(19) . . . no C18 C17 H17 119.3(18) . . . no C13 C18 H18 118.3(15) . . . no C17 C18 H18 119.7(15) . . . no N1 C1 C2 123.2(2) . . . yes C1 C2 C3 118.1(2) . . . no C2 C3 C4 118.9(2) . . . no C4 C3 C6 117.9(2) . . . no C2 C3 C6 123.2(2) . . . no C3 C4 C5 119.2(2) . . . no N1 C5 C4 122.1(2) . . . yes O1 C6 C3 121.3(2) . . . yes N2 C6 C3 115.96(19) . . . yes O1 C6 N2 122.8(2) . . . yes N1 C1 H1 109.7(18) . . . no C2 C1 H1 127.1(18) . . . no C1 C2 H2 120(2) . . . no C3 C2 H2 122(2) . . . no C3 C4 H4 121(2) . . . no C5 C4 H4 120(2) . . . no N1 C5 H5 115.6(19) . . . no C4 C5 H5 122.3(19) . . . 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 N4 C7 C8 1.4(4) . . . . no C7 N4 C11 C10 -0.9(4) . . . . no N6 N5 C12 O2 -1.4(4) . . . . no N6 N5 C12 C9 177.8(2) . . . . no C1 N1 C5 C4 -0.5(4) . . . . no C5 N1 C1 C2 0.7(4) . . . . no N3 N2 C6 C3 179.0(3) . . . . no N3 N2 C6 O1 -0.7(5) . . . . no N4 C7 C8 C9 -0.7(4) . . . . no C7 C8 C9 C12 -178.5(2) . . . . no C7 C8 C9 C10 -0.4(4) . . . . no C10 C9 C12 N5 154.7(2) . . . . no C12 C9 C10 C11 179.0(2) . . . . no C8 C9 C12 O2 152.1(3) . . . . no C8 C9 C10 C11 0.9(3) . . . . no C10 C9 C12 O2 -26.1(4) . . . . no C8 C9 C12 N5 -27.2(4) . . . . no C9 C10 C11 N4 -0.2(4) . . . . no C26 C20 C21 O8 -6.1(3) . . . . no C26 C20 C25 C24 -173.8(2) . . . . no C21 C20 C26 O6 -0.8(3) . . . . no C21 C20 C25 C24 3.4(3) . . . . no C25 C20 C26 O6 176.3(2) . . . . no C25 C20 C26 O7 -2.9(3) . . . . no C25 C20 C21 C22 -3.6(3) . . . . no C21 C20 C26 O7 180.0(2) . . . . no C26 C20 C21 C22 173.6(2) . . . . no C25 C20 C21 O8 176.7(2) . . . . no O8 C21 C22 C23 -179.6(2) . . . . no C20 C21 C22 C23 0.8(4) . . . . no C21 C22 C23 C24 2.5(4) . . . . no C21 C22 C23 N8 -179.3(3) . . . . no C22 C23 C24 C25 -2.8(4) . . . . no N8 C23 C24 C25 179.0(3) . . . . no C23 C24 C25 C20 -0.2(4) . . . . no C18 C13 C14 C15 -0.8(3) . . . . no C19 C13 C18 C17 -178.3(2) . . . . no C19 C13 C14 C15 178.3(2) . . . . no C14 C13 C18 C17 0.7(3) . . . . no C18 C13 C19 O3 -171.6(2) . . . . no C18 C13 C19 O4 9.5(4) . . . . no C19 C13 C14 O5 -1.2(3) . . . . no C14 C13 C19 O4 -169.5(2) . . . . no C18 C13 C14 O5 179.7(2) . . . . no C14 C13 C19 O3 9.3(4) . . . . no C13 C14 C15 C16 -0.6(3) . . . . no O5 C14 C15 C16 178.9(2) . . . . no C14 C15 C16 N7 179.5(2) . . . . no C14 C15 C16 C17 2.2(4) . . . . no C15 C16 C17 C18 -2.2(4) . . . . no N7 C16 C17 C18 -179.6(2) . . . . no C16 C17 C18 C13 0.8(3) . . . . no N1 C1 C2 C3 -0.1(4) . . . . no C1 C2 C3 C4 -0.7(4) . . . . no C1 C2 C3 C6 -179.4(2) . . . . no C2 C3 C6 N2 -25.9(4) . . . . no C4 C3 C6 O1 -24.9(4) . . . . no C4 C3 C6 N2 155.4(3) . . . . no C2 C3 C6 O1 153.8(3) . . . . no C2 C3 C4 C5 0.9(4) . . . . no C6 C3 C4 C5 179.7(2) . . . . no C3 C4 C5 N1 -0.3(4) . . . . 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 O1 N6 3.010(3) . 3_555 no O1 O6 3.171(3) . . no O1 N3 2.764(3) . . no O1 C7 3.350(3) . . no O2 N3 3.038(3) . 3_544 no O2 N6 2.785(3) . . no O2 O8 3.100(3) . 3_545 no O3 C1 3.319(3) . 2_654 no O3 O5 2.591(2) . . no O3 N8 3.053(3) . 1_545 no O4 N1 2.575(3) . 2_654 no O4 C1 3.401(3) . 2_654 no O5 N5 3.028(3) . . no O5 O3 2.591(2) . . no O6 O8 2.554(3) . . no O6 N6 3.258(4) . 3_554 no O6 O1 3.171(3) . . no O6 N7 3.023(3) . . no O8 N2 3.015(3) . 2_664 no O8 O2 3.100(3) . 3_554 no O8 O6 2.554(3) . . no O1 H6B 2.16(3) . 3_555 no O1 H3A 2.61(4) . . no O1 H3B 2.64(5) . . no O1 H7 2.42(3) . . no O1 H4 2.58(3) . . no O2 H3B 2.13(5) . 3_544 no O2 H10 2.60(3) . . no O2 H6B 2.68(3) . . no O3 H8A 2.29(4) . 1_545 no O3 H1 2.62(3) . 2_654 no O3 H5O 1.81(4) . . no O4 H11 2.64(3) . 4_555 no O4 H18 2.45(2) . . no O5 H25 2.70(3) . 3_544 no O5 H5N 2.17(4) . . no O6 H7 2.89(3) . . no O6 H6A 2.39(7) . 3_554 no O6 H8O 1.57(5) . . no O6 H7A 2.23(3) . . no O7 H25 2.38(3) . . no O7 H5 2.64(3) . 3_554 no O8 H17 2.91(3) . 2_665 no O8 H3A 2.67(4) . . no O8 H2N 2.18(4) . 2_664 no N1 C19 3.315(3) . 2_655 no N1 O4 2.575(3) . 2_655 no N2 O8 3.015(3) . 2_665 no N3 O2 3.038(3) . 3_555 no N3 O1 2.764(3) . . no N3 N7 3.093(3) . 2_665 no N5 O5 3.028(3) . . no N6 O6 3.258(4) . 3_545 no N6 O2 2.785(3) . . no N6 N8 3.170(3) . 1_545 no N6 O1 3.010(3) . 3_544 no N7 N3 3.093(3) . 2_664 no N7 O6 3.023(3) . . no N8 C11 3.288(4) . 3_555 no N8 O3 3.053(3) . 1_565 no N8 N6 3.170(3) . 1_565 no N1 H4O 1.68(5) . 2_655 no N2 H2 2.68(3) . . no N3 H7B 2.14(3) . 2_665 no N5 H8 2.69(3) . . no N6 H24 2.89(3) . 1_545 no N6 H8B 2.28(3) . 1_545 no C1 C18 3.560(4) . . no C1 C13 3.327(4) . . no C1 O3 3.319(3) . 2_655 no C1 O4 3.401(3) . 2_655 no C2 C16 3.567(4) . . no C2 C18 3.588(4) . . no C2 C17 3.537(4) . . no C3 C17 3.422(3) . 1_556 no C3 C16 3.543(4) . . no C3 C15 3.439(3) . . no C4 C15 3.586(4) . . no C4 C25 3.563(3) . 3_545 no C4 C17 3.518(4) . 1_556 no C4 C16 3.585(4) . 1_556 no C5 C14 3.585(4) . . no C5 C18 3.559(4) . 1_556 no C5 C13 3.432(4) . 1_556 no C7 O1 3.350(3) . . no C7 C24 3.537(4) . 3_545 no C7 C23 3.425(4) . 3_545 no C8 C15 3.593(3) . . no C8 C23 3.495(4) . 3_545 no C8 C24 3.494(4) . 3_545 no C8 C25 3.553(4) . 3_545 no C9 C22 3.553(4) . 3_545 no C9 C21 3.528(3) . 3_545 no C10 C22 3.442(4) . 3_544 no C10 C23 3.352(4) . 3_544 no C10 C18 3.574(3) . 4_455 no C11 N8 3.288(4) . 3_544 no C11 C23 3.348(4) . 3_544 no C12 C21 3.483(4) . 3_545 no C13 C5 3.432(4) . 1_554 no C13 C1 3.327(4) . . no C14 C5 3.585(4) . . no C15 C8 3.593(3) . . no C15 C4 3.586(4) . . no C15 C3 3.439(3) . . no C15 C25 3.534(3) . 3_544 no C16 C3 3.543(4) . . no C16 C4 3.585(4) . 1_554 no C16 C2 3.567(4) . . no C17 C4 3.518(4) . 1_554 no C17 C2 3.537(4) . . no C17 C3 3.422(3) . 1_554 no C18 C2 3.588(4) . . no C18 C10 3.574(3) . 4_555 no C18 C5 3.559(4) . 1_554 no C18 C1 3.560(4) . . no C19 N1 3.315(3) . 2_654 no C21 C12 3.483(4) . 3_554 no C21 C9 3.528(3) . 3_554 no C22 C10 3.442(4) . 3_555 no C22 C9 3.553(4) . 3_554 no C23 C10 3.352(4) . 3_555 no C23 C7 3.425(4) . 3_554 no C23 C11 3.348(4) . 3_555 no C23 C8 3.495(4) . 3_554 no C24 C8 3.494(4) . 3_554 no C24 C7 3.537(4) . 3_554 no C25 C15 3.534(3) . 3_555 no C25 C4 3.563(3) . 3_554 no C25 C8 3.553(4) . 3_554 no C1 H4O 2.62(5) . 2_655 no C1 H22 2.88(3) . 2_665 no C2 H2N 2.67(3) . . no C2 H22 2.86(3) . 2_665 no C4 H25 3.03(3) . 3_545 no C5 H4O 2.65(5) . 2_655 no C5 H25 3.09(3) . 3_545 no C7 H15A 2.77(3) . . no C8 H15A 2.68(3) . . no C8 H5N 2.65(3) . . no C10 H2 3.05(3) . 4_455 no C11 H1 2.90(3) . 4_455 no C14 H25 2.81(3) . 3_544 no C15 H25 2.87(3) . 3_544 no C17 H10 2.91(3) . 4_555 no C18 H22 3.08(3) . 2_664 no C18 H10 2.74(3) . 4_555 no C19 H5O 2.38(4) . . no C22 H18 2.93(3) . 2_665 no C24 H4 2.93(3) . 3_554 no C25 H4 2.79(3) . 3_554 no C25 H15A 3.10(3) . 3_555 no C25 H8 3.06(4) . 3_554 no C26 H8O 2.13(4) . . no C26 H6A 3.05(7) . 3_554 no H1 H4O 2.57(6) . 2_655 no H1 O3 2.62(3) . 2_655 no H1 C11 2.90(3) . 4_555 no H2 H2N 2.27(5) . . no H2 C10 3.05(3) . 4_555 no H2 N2 2.68(3) . . no H2N C2 2.67(3) . . no H2N H2 2.27(5) . . no H2N O8 2.18(4) . 2_665 no H3A O8 2.67(4) . . no H3A H7B 2.57(6) . 2_665 no H3A H8O 2.56(7) . . no H3A O1 2.61(4) . . no H3B O1 2.64(5) . . no H3B O2 2.13(5) . 3_555 no H4 C25 2.79(3) . 3_545 no H4 C24 2.93(3) . 3_545 no H4 O1 2.58(3) . . no H4 H25 2.44(5) . 3_545 no H4O H1 2.57(6) . 2_654 no H4O C5 2.65(5) . 2_654 no H4O C1 2.62(5) . 2_654 no H4O N1 1.68(5) . 2_654 no H5 O7 2.64(3) . 3_545 no H5 H25 2.59(5) . 3_545 no H5N O5 2.17(4) . . no H5N C8 2.65(3) . . no H5N H5O 2.50(5) . . no H5N H8 2.29(5) . . no H5O O3 1.81(4) . . no H5O C19 2.38(4) . . no H5O H5N 2.50(5) . . no H6A H8B 2.48(7) . 1_545 no H6A C26 3.05(7) . 3_545 no H6A H24 2.54(6) . 1_545 no H6A O6 2.39(7) . 3_545 no H6B O1 2.16(3) . 3_544 no H6B O2 2.68(3) . . no H7 O1 2.42(3) . . no H7 O6 2.89(3) . . no H7A H15A 2.49(4) . . no H7A O6 2.23(3) . . no H7B H3A 2.57(6) . 2_664 no H7B H17 2.42(5) . . no H7B N3 2.14(3) . 2_664 no H8 C25 3.06(4) . 3_545 no H8 H15A 2.58(5) . . no H8 N5 2.69(3) . . no H8 H5N 2.29(5) . . no H8A O3 2.29(4) . 1_565 no H8A H22 2.39(5) . . no H8B N6 2.28(3) . 1_565 no H8B H6A 2.48(7) . 1_565 no H8B H24 2.31(5) . . no H8O H3A 2.56(7) . . no H8O O6 1.57(5) . . no H8O C26 2.13(4) . . no H10 O2 2.60(3) . . no H10 C17 2.91(3) . 4_455 no H10 C18 2.74(3) . 4_455 no H10 H18 2.42(4) . 4_455 no H11 O4 2.64(3) . 4_455 no H15A H8 2.58(5) . . no H15A C7 2.77(3) . . no H15A C8 2.68(3) . . no H15A H7A 2.49(4) . . no H15A C25 3.10(3) . 3_544 no H17 O8 2.91(3) . 2_664 no H17 H7B 2.42(5) . . no H18 O4 2.45(2) . . no H18 H10 2.42(4) . 4_555 no H18 C22 2.93(3) . 2_664 no H18 H22 2.36(4) . 2_664 no H22 H18 2.36(4) . 2_665 no H22 H8A 2.39(5) . . no H22 C1 2.88(3) . 2_664 no H22 C2 2.86(3) . 2_664 no H22 C18 3.08(3) . 2_665 no H24 H8B 2.31(5) . . no H24 N6 2.89(3) . 1_565 no H24 H6A 2.54(6) . 1_565 no H25 H5 2.59(5) . 3_554 no H25 O7 2.38(3) . . no H25 O5 2.70(4) . 3_555 no H25 C4 3.03(3) . 3_554 no H25 C5 3.09(3) . 3_554 no H25 C14 2.81(3) . 3_555 no H25 C15 2.87(3) . 3_555 no H25 H4 2.44(5) . 3_554 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # N2 H2N O8 0.87(3) 2.18(4) 3.015(3) 159(4) 2_665 yes N3 H3B O2 1.01(5) 2.13(5) 3.038(3) 149(4) 3_555 yes O4 H4O N1 0.90(5) 1.68(5) 2.575(3) 171(4) 2_654 yes N5 H5N O5 0.88(3) 2.17(4) 3.028(3) 168(3) . yes O5 H5O O3 0.90(3) 1.81(4) 2.591(2) 145(3) . yes N6 H6A O6 1.01(7) 2.39(7) 3.258(4) 144(4) 3_545 yes N6 H6B O1 0.89(3) 2.16(3) 3.010(3) 159(3) 3_544 yes N7 H7A O6 0.90(4) 2.23(3) 3.023(3) 147(3) . yes N7 H7B N3 0.97(3) 2.14(3) 3.093(3) 168(3) 2_664 yes O7 H7O N4 1.21(5) 1.35(5) 2.553(3) 178(6) . yes N8 H8A O3 0.81(4) 2.29(4) 3.053(3) 156(3) 1_565 yes N8 H8B N6 0.90(3) 2.28(3) 3.170(3) 173(3) 1_565 yes O8 H8O O6 1.02(5) 1.57(5) 2.554(3) 161(4) . yes C7 H7 O1 0.94(3) 2.42(3) 3.350(3) 170(3) . yes C25 H25 O7 1.02(3) 2.38(3) 2.787(3) 103(2) . yes #===END # Attachment 'web_deposit_cif_file_3_PawelGrobelny_1289286463.cif' # CIF-file generated for datam in Pna2(1) data_datam4 _database_code_depnum_ccdc_archive 'CCDC 800233' #TrackingRef 'web_deposit_cif_file_3_PawelGrobelny_1289286463.cif' _chemical_name_systematic ; ; _chemical_name_common 'Isoniazid:4-aminosalicylic acid co-crystal' _chemical_melting_point ? _chemical_formula_moiety 'C13 H14 N4 O4, C7 H7 N O3, C6 H7 N3 O' _chemical_formula_structural ? _chemical_formula_sum 'C26 H28 N8 O8' _chemical_formula_iupac ? _chemical_formula_weight 580.56 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_space_group_name_H-M 'P n a 21' _symmetry_Int_Tables_number 33 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,1/2+z 3 1/2-x,1/2+y,1/2+z 4 1/2+x,1/2-y,z _cell_length_a 21.879(9) _cell_length_b 16.520(7) _cell_length_c 7.263(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2625.3(19) _cell_formula_units_Z 4 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 6746 _cell_measurement_theta_min 1.9 _cell_measurement_theta_max 27.5 _cell_special_details ; ; _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.469 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 0.112 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.836 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' #=============================================================================== _exptl_special_details ; ; _diffrn_ambient_temperature 160(2) _diffrn_source_power 0.6 _diffrn_source_voltage 50.0 _diffrn_source_current 12.0 _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_source 'Sealed Tube' _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_measurement_specimen_support Fiber _diffrn_detector CCD _diffrn_measurement_device ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_detector_area_resol_mean 13.6612 _diffrn_measurement_method 'profile data from \w-scans' _diffrn_reflns_number 21255 _diffrn_reflns_av_R_equivalents 0.0493 _diffrn_reflns_av_sigmaI/netI 0.0295 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 27.44 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.44 _diffrn_measured_fraction_theta_full 0.998 _reflns_number_total 3245 _reflns_number_gt 3040 _reflns_threshold_expression >2\s(I) _diffrn_measurement_details ; scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 0.0000 XTD: 49.4369 2theta: 29.5316 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 120.0000 XTD: 49.4369 2theta: 29.5316 scan: Number of images: 67 Slice: -60.0000 - 7.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 240.0000 XTD: 49.4369 2theta: 29.5316 ; _diffrn_orient_matrix_UB_11 0.016165 _diffrn_orient_matrix_UB_12 -0.135688 _diffrn_orient_matrix_UB_13 0.016806 _diffrn_orient_matrix_UB_21 0.060047 _diffrn_orient_matrix_UB_22 0.007396 _diffrn_orient_matrix_UB_23 0.001956 _diffrn_orient_matrix_UB_31 -0.002138 _diffrn_orient_matrix_UB_32 0.005361 _diffrn_orient_matrix_UB_33 0.045341 _diffrn_orient_matrix_type d*Trek _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement ? _computing_molecular_graphics ? _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== _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^ > 2\s(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^)+(0.0667P)^2^+0.2333P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3245 _refine_ls_number_parameters 492 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0436 _refine_ls_R_factor_gt 0.0386 _refine_ls_wR_factor_ref 0.1169 _refine_ls_wR_factor_gt 0.1053 _refine_ls_goodness_of_fit_ref 1.171 _refine_ls_restrained_S_all 1.171 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.235 _refine_diff_density_min -0.208 _refine_diff_density_rms 0.057 #=============================================================================== loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags O2 O Uani 0.11423(9) 0.10547(11) 0.9162(4) 1.000 0.0394(6) . . O6 O Uani 0.31662(9) 0.50669(11) 0.9862(3) 1.000 0.0386(6) . . O7 O Uani 0.22124(8) 0.53733(10) 0.9008(4) 1.000 0.0378(6) . . O8 O Uani 0.39842(9) 0.61723(12) 0.9902(3) 1.000 0.0374(6) . . N4 N Uani 0.20085(10) 0.38484(12) 0.9102(4) 1.000 0.0303(6) . . N5 N Uani 0.21581(10) 0.08116(12) 0.9303(4) 1.000 0.0314(6) . . N6 N Uani 0.21012(13) -0.00505(13) 0.9284(4) 1.000 0.0385(8) . . N8 N Uani 0.33249(12) 0.89188(13) 0.9192(4) 1.000 0.0368(7) . . C7 C Uani 0.24334(12) 0.33388(15) 0.8459(4) 1.000 0.0291(7) . . C8 C Uani 0.23515(11) 0.25018(15) 0.8474(4) 1.000 0.0268(8) . . C9 C Uani 0.18114(11) 0.21922(13) 0.9174(4) 1.000 0.0248(6) . . C10 C Uani 0.13691(11) 0.27230(15) 0.9814(4) 1.000 0.0266(7) . . C11 C Uani 0.14837(11) 0.35537(15) 0.9765(4) 1.000 0.0297(7) . . C12 C Uani 0.16715(11) 0.12957(14) 0.9222(4) 1.000 0.0282(7) . . C20 C Uani 0.29276(11) 0.64374(14) 0.9184(4) 1.000 0.0258(6) . . C21 C Uani 0.35268(11) 0.67117(15) 0.9542(3) 1.000 0.0272(7) . . C22 C Uani 0.36580(12) 0.75324(16) 0.9539(4) 1.000 0.0296(7) . . C23 C Uani 0.32016(11) 0.81085(14) 0.9175(4) 1.000 0.0280(7) . . C24 C Uani 0.26096(12) 0.78345(15) 0.8712(4) 1.000 0.0278(7) . . C25 C Uani 0.24848(11) 0.70161(14) 0.8725(3) 1.000 0.0260(7) . . C26 C Uani 0.27738(11) 0.55718(14) 0.9363(4) 1.000 0.0288(7) . . O3 O Uani 0.42397(9) 0.00228(10) 0.1144(3) 1.000 0.0400(7) . . O4 O Uani 0.52130(8) 0.03651(10) 0.1708(4) 1.000 0.0381(6) . . O5 O Uani 0.34717(8) 0.11651(11) 0.0365(3) 1.000 0.0340(6) . . N7 N Uani 0.40891(12) 0.38968(13) 0.1445(4) 1.000 0.0376(8) . . C13 C Uani 0.44925(11) 0.14109(14) 0.1486(4) 1.000 0.0256(6) . . C14 C Uani 0.39152(11) 0.16921(15) 0.0928(4) 1.000 0.0267(7) . . C15 C Uani 0.37828(11) 0.25136(15) 0.0914(4) 1.000 0.0270(7) . . C16 C Uani 0.42225(11) 0.30809(14) 0.1448(4) 1.000 0.0277(7) . . C17 C Uani 0.48001(12) 0.28058(15) 0.2045(4) 1.000 0.0282(7) . . C18 C Uani 0.49271(11) 0.19888(15) 0.2048(4) 1.000 0.0269(7) . . C19 C Uani 0.46390(11) 0.05427(15) 0.1436(4) 1.000 0.0298(7) . . O1 O Uani 0.37605(8) 0.39971(11) 0.6692(3) 1.000 0.0389(6) . . N1 N Uani 0.45661(10) 0.11683(13) 0.6594(3) 1.000 0.0303(6) . . N2 N Uani 0.47756(10) 0.42099(12) 0.6511(4) 1.000 0.0368(7) . . N3 N Uani 0.47327(12) 0.50616(14) 0.6510(6) 1.000 0.0446(8) . . C1 C Uani 0.50058(12) 0.16618(16) 0.7196(4) 1.000 0.0313(7) . . C2 C Uani 0.49473(12) 0.24952(15) 0.7230(4) 1.000 0.0283(8) . . C3 C Uani 0.44037(11) 0.28353(14) 0.6619(4) 1.000 0.0253(6) . . C4 C Uani 0.39409(12) 0.23248(17) 0.6012(4) 1.000 0.0295(7) . . C5 C Uani 0.40384(12) 0.14951(16) 0.6013(4) 1.000 0.0310(7) . . C6 C Uani 0.42816(11) 0.37308(14) 0.6611(4) 1.000 0.0285(7) . . H5A H Uiso 0.2558(15) 0.1001(17) 0.950(5) 1.000 0.036(8) . . H6A H Uiso 0.202(3) -0.028(4) 0.809(11) 1.000 0.12(2) . . H6B H Uiso 0.1848(18) -0.023(2) 1.014(6) 1.000 0.045(10) . . H7 H Uiso 0.2801(14) 0.3551(18) 0.811(5) 1.000 0.031(8) . . H7O H Uiso 0.212(2) 0.467(3) 0.902(9) 1.000 0.101(17) . . H8 H Uiso 0.2671(14) 0.2138(19) 0.796(5) 1.000 0.038(9) . . H8A H Uiso 0.3666(18) 0.909(2) 0.961(6) 1.000 0.048(10) . . H8B H Uiso 0.2998(14) 0.9247(18) 0.920(5) 1.000 0.028(7) . . H8O H Uiso 0.370(2) 0.565(3) 0.981(8) 1.000 0.098(17) . . H10 H Uiso 0.0982(14) 0.2524(19) 1.035(5) 1.000 0.036(8) . . H11 H Uiso 0.1185(14) 0.3974(18) 1.029(5) 1.000 0.032(8) . . H22 H Uiso 0.4030(16) 0.773(2) 0.985(5) 1.000 0.043(9) . . H24 H Uiso 0.2293(14) 0.8226(19) 0.849(5) 1.000 0.037(9) . . H25 H Uiso 0.2071(13) 0.6780(17) 0.841(5) 1.000 0.031(8) . . H4O H Uiso 0.533(2) -0.020(3) 0.166(9) 1.000 0.082(14) . . H5O H Uiso 0.3629(16) 0.063(2) 0.052(6) 1.000 0.050(10) . . H7A H Uiso 0.4420(16) 0.428(2) 0.159(6) 1.000 0.053(10) . . H7B H Uiso 0.3759(19) 0.404(2) 0.068(6) 1.000 0.058(12) . . H15 H Uiso 0.3343(16) 0.2668(19) 0.057(5) 1.000 0.045(9) . . H17 H Uiso 0.5099(14) 0.3200(18) 0.243(5) 1.000 0.032(8) . . H18 H Uiso 0.5293(14) 0.1806(17) 0.247(5) 1.000 0.030(8) . . H1 H Uiso 0.5382(14) 0.1348(19) 0.765(5) 1.000 0.040(9) . . H2 H Uiso 0.5229(14) 0.2775(19) 0.763(5) 1.000 0.034(8) . . H2N H Uiso 0.5151(18) 0.406(2) 0.627(6) 1.000 0.059(12) . . H3A H Uiso 0.443(2) 0.520(3) 0.550(7) 1.000 0.062(12) . . H3B H Uiso 0.453(2) 0.516(3) 0.757(7) 1.000 0.058(12) . . H4 H Uiso 0.3569(16) 0.253(2) 0.564(5) 1.000 0.047(10) . . H5 H Uiso 0.3712(15) 0.1095(19) 0.561(5) 1.000 0.041(9) . . 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 O2 0.0233(9) 0.0314(9) 0.0634(13) 0.0035(10) -0.0022(10) -0.0080(7) O6 0.0307(10) 0.0282(9) 0.0568(13) -0.0005(9) -0.0051(10) 0.0063(7) O7 0.0284(10) 0.0243(8) 0.0608(13) 0.0021(9) -0.0081(10) -0.0023(7) O8 0.0200(9) 0.0395(10) 0.0528(13) 0.0050(9) -0.0011(9) 0.0042(7) N4 0.0284(11) 0.0260(10) 0.0364(12) 0.0009(10) -0.0040(10) -0.0027(8) N5 0.0279(11) 0.0200(9) 0.0464(13) -0.0009(10) -0.0050(11) -0.0022(8) N6 0.0406(13) 0.0204(10) 0.0544(16) -0.0003(11) -0.0016(13) -0.0027(9) N8 0.0340(14) 0.0280(10) 0.0483(14) -0.0006(11) -0.0034(12) -0.0076(10) C7 0.0229(12) 0.0284(12) 0.0361(13) 0.0032(11) -0.0007(11) -0.0034(9) C8 0.0227(12) 0.0291(13) 0.0286(14) -0.0008(10) -0.0013(10) -0.0017(10) C9 0.0223(11) 0.0239(10) 0.0282(11) -0.0003(10) -0.0042(10) -0.0032(8) C10 0.0202(11) 0.0298(11) 0.0297(12) -0.0015(10) -0.0025(10) -0.0035(9) C11 0.0259(12) 0.0291(11) 0.0341(13) -0.0010(10) -0.0037(11) 0.0010(10) C12 0.0264(12) 0.0264(10) 0.0319(12) -0.0008(11) -0.0040(11) -0.0023(9) C20 0.0205(11) 0.0282(11) 0.0287(11) -0.0023(10) 0.0009(10) -0.0007(9) C21 0.0209(11) 0.0342(12) 0.0266(12) 0.0013(10) 0.0003(10) 0.0028(9) C22 0.0207(11) 0.0370(13) 0.0310(13) 0.0006(11) -0.0016(10) -0.0062(10) C23 0.0286(12) 0.0301(11) 0.0254(11) -0.0012(10) -0.0005(11) -0.0069(9) C24 0.0255(12) 0.0272(12) 0.0308(14) -0.0008(10) 0.0000(11) -0.0015(10) C25 0.0216(12) 0.0272(11) 0.0293(13) -0.0007(10) -0.0024(10) -0.0010(9) C26 0.0264(12) 0.0259(11) 0.0342(13) -0.0022(10) 0.0002(11) 0.0033(9) O3 0.0284(10) 0.0268(8) 0.0647(15) -0.0051(9) -0.0029(10) -0.0048(7) O4 0.0260(9) 0.0254(8) 0.0628(13) -0.0005(10) -0.0032(10) 0.0002(7) O5 0.0219(9) 0.0314(9) 0.0487(11) -0.0013(9) -0.0058(9) -0.0052(7) N7 0.0336(13) 0.0261(10) 0.0532(16) 0.0000(11) -0.0048(12) 0.0022(9) C13 0.0242(11) 0.0247(10) 0.0278(11) -0.0017(10) 0.0014(10) -0.0037(9) C14 0.0213(11) 0.0305(12) 0.0284(11) -0.0014(10) 0.0028(10) -0.0050(9) C15 0.0207(11) 0.0317(12) 0.0286(13) 0.0017(10) -0.0001(10) -0.0013(9) C16 0.0275(12) 0.0276(11) 0.0281(12) -0.0016(10) 0.0030(11) -0.0008(9) C17 0.0247(12) 0.0287(12) 0.0312(13) -0.0043(11) -0.0003(11) -0.0053(9) C18 0.0196(11) 0.0318(12) 0.0294(13) -0.0002(11) -0.0005(10) -0.0020(9) C19 0.0254(12) 0.0284(12) 0.0357(13) -0.0013(11) 0.0002(11) -0.0014(9) O1 0.0254(9) 0.0333(9) 0.0580(13) 0.0050(10) 0.0059(10) 0.0053(7) N1 0.0280(10) 0.0273(9) 0.0355(12) 0.0024(10) 0.0003(9) -0.0009(8) N2 0.0249(11) 0.0248(10) 0.0606(16) 0.0004(12) 0.0074(12) 0.0018(8) N3 0.0318(12) 0.0249(10) 0.077(2) 0.0028(14) 0.0049(16) -0.0019(9) C1 0.0263(12) 0.0349(13) 0.0326(13) 0.0026(11) -0.0014(11) 0.0007(10) C2 0.0231(12) 0.0308(13) 0.0309(14) 0.0013(10) -0.0015(10) -0.0030(10) C3 0.0214(11) 0.0297(11) 0.0249(11) 0.0010(10) 0.0039(10) 0.0003(9) C4 0.0214(11) 0.0367(13) 0.0304(12) 0.0012(11) 0.0005(10) 0.0015(10) C5 0.0247(13) 0.0327(12) 0.0356(13) -0.0024(11) -0.0011(11) -0.0040(10) C6 0.0230(12) 0.0282(11) 0.0342(13) 0.0011(11) 0.0040(10) 0.0039(9) #=============================================================================== _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; 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 O2 C12 1.225(3) . . yes O6 C26 1.251(3) . . yes O7 C26 1.297(3) . . yes O8 C21 1.365(3) . . yes O7 H7O 1.18(5) . . no O8 H8O 1.07(5) . . no O3 C19 1.243(3) . . yes O4 C19 1.305(3) . . yes O5 C14 1.366(3) . . yes O4 H4O 0.97(5) . . no O5 H5O 0.96(3) . . no O1 C6 1.224(3) . . yes N4 C7 1.338(3) . . yes N4 C11 1.337(3) . . yes N5 N6 1.430(3) . . yes N5 C12 1.333(3) . . yes N8 C23 1.366(3) . . yes N4 H7O 1.38(5) . . no N5 H5A 0.94(3) . . no N6 H6A 0.96(8) . . no N6 H6B 0.88(4) . . no N8 H8A 0.85(4) . . no N8 H8B 0.90(3) . . no N7 C16 1.379(3) . . yes N7 H7B 0.94(4) . . no N7 H7A 0.97(3) . . no N1 C5 1.343(3) . . yes N1 C1 1.335(3) . . yes N2 C6 1.342(3) . . yes N2 N3 1.410(3) . . yes N2 H2N 0.88(4) . . no N3 H3A 1.01(5) . . no N3 H3B 0.90(5) . . no C7 C8 1.394(4) . . no C8 C9 1.384(4) . . no C9 C10 1.386(3) . . no C9 C12 1.513(3) . . no C10 C11 1.396(4) . . no C20 C25 1.401(3) . . no C20 C26 1.475(3) . . no C20 C21 1.411(3) . . no C21 C22 1.386(4) . . no C22 C23 1.405(4) . . no C23 C24 1.413(4) . . no C24 C25 1.379(3) . . no C7 H7 0.91(3) . . no C8 H8 1.00(3) . . no C10 H10 0.99(3) . . no C11 H11 1.03(3) . . no C22 H22 0.91(4) . . no C24 H24 0.96(3) . . no C25 H25 1.01(3) . . no C13 C14 1.406(4) . . no C13 C19 1.470(3) . . no C13 C18 1.408(4) . . no C14 C15 1.388(4) . . no C15 C16 1.398(4) . . no C16 C17 1.411(4) . . no C17 C18 1.378(4) . . no C15 H15 1.03(3) . . no C17 H17 0.96(3) . . no C18 H18 0.91(3) . . no C1 C2 1.383(4) . . no C2 C3 1.388(4) . . no C3 C4 1.390(4) . . no C3 C6 1.503(3) . . no C4 C5 1.387(4) . . no C1 H1 1.03(3) . . no C2 H2 0.82(3) . . no C4 H4 0.92(3) . . no C5 H5 1.02(3) . . 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 C26 O7 H7O 114(2) . . . no C21 O8 H8O 95(3) . . . no C19 O4 H4O 118(3) . . . no C14 O5 H5O 107(2) . . . no C7 N4 C11 119.6(2) . . . yes N6 N5 C12 121.9(2) . . . yes C11 N4 H7O 122(2) . . . no C7 N4 H7O 119(2) . . . no C12 N5 H5A 123.4(17) . . . no N6 N5 H5A 114.5(17) . . . no H6A N6 H6B 113(5) . . . no N5 N6 H6B 113(2) . . . no N5 N6 H6A 115(4) . . . no H8A N8 H8B 120(3) . . . no C23 N8 H8B 115.8(19) . . . no C23 N8 H8A 120(2) . . . no C16 N7 H7A 119(2) . . . no H7A N7 H7B 118(3) . . . no C16 N7 H7B 114(2) . . . no C1 N1 C5 118.5(2) . . . yes N3 N2 C6 122.4(2) . . . yes C6 N2 H2N 127(2) . . . no N3 N2 H2N 110(2) . . . no N2 N3 H3B 102(3) . . . no N2 N3 H3A 106(3) . . . no H3A N3 H3B 105(4) . . . no N4 C7 C8 122.1(2) . . . yes C7 C8 C9 118.6(2) . . . no C8 C9 C12 122.9(2) . . . no C10 C9 C12 118.1(2) . . . no C8 C9 C10 119.0(2) . . . no C9 C10 C11 119.2(2) . . . no N4 C11 C10 121.4(2) . . . yes O2 C12 N5 124.2(2) . . . yes O2 C12 C9 120.6(2) . . . yes N5 C12 C9 115.3(2) . . . yes C25 C20 C26 121.7(2) . . . no C21 C20 C26 120.5(2) . . . no C21 C20 C25 117.8(2) . . . no O8 C21 C22 119.1(2) . . . yes O8 C21 C20 120.4(2) . . . yes C20 C21 C22 120.4(2) . . . no C21 C22 C23 121.1(2) . . . no N8 C23 C22 121.5(2) . . . yes C22 C23 C24 118.7(2) . . . no N8 C23 C24 119.8(2) . . . yes C23 C24 C25 119.6(2) . . . no C20 C25 C24 122.2(2) . . . no O6 C26 C20 121.0(2) . . . yes O7 C26 C20 116.3(2) . . . yes O6 C26 O7 122.6(2) . . . yes C8 C7 H7 119.7(19) . . . no N4 C7 H7 117.9(19) . . . no C7 C8 H8 120.4(18) . . . no C9 C8 H8 121.0(18) . . . no C11 C10 H10 119.4(19) . . . no C9 C10 H10 121.3(19) . . . no C10 C11 H11 122.8(17) . . . no N4 C11 H11 115.7(17) . . . no C21 C22 H22 123(2) . . . no C23 C22 H22 116(2) . . . no C23 C24 H24 119.0(19) . . . no C25 C24 H24 121.2(19) . . . no C20 C25 H25 114.2(16) . . . no C24 C25 H25 123.6(16) . . . no C14 C13 C18 117.8(2) . . . no C14 C13 C19 120.8(2) . . . no C18 C13 C19 121.4(2) . . . no O5 C14 C13 120.9(2) . . . yes C13 C14 C15 120.9(2) . . . no O5 C14 C15 118.2(2) . . . yes C14 C15 C16 120.7(2) . . . no C15 C16 C17 119.1(2) . . . no N7 C16 C15 120.6(2) . . . yes N7 C16 C17 120.3(2) . . . yes C16 C17 C18 119.8(2) . . . no C13 C18 C17 121.8(2) . . . no O3 C19 O4 123.2(2) . . . yes O4 C19 C13 115.2(2) . . . yes O3 C19 C13 121.7(2) . . . yes C16 C15 H15 123.1(18) . . . no C14 C15 H15 116.1(18) . . . no C16 C17 H17 118.6(18) . . . no C18 C17 H17 121.6(18) . . . no C13 C18 H18 117.9(18) . . . no C17 C18 H18 120.2(18) . . . no N1 C1 C2 123.2(2) . . . yes C1 C2 C3 118.5(2) . . . no C2 C3 C4 118.7(2) . . . no C4 C3 C6 117.8(2) . . . no C2 C3 C6 123.5(2) . . . no C3 C4 C5 119.2(2) . . . no N1 C5 C4 122.0(2) . . . yes O1 C6 C3 121.3(2) . . . yes N2 C6 C3 116.0(2) . . . yes O1 C6 N2 122.8(2) . . . yes N1 C1 H1 112.0(18) . . . no C2 C1 H1 124.8(18) . . . no C1 C2 H2 120(2) . . . no C3 C2 H2 122(2) . . . no C3 C4 H4 121(2) . . . no C5 C4 H4 120(2) . . . no N1 C5 H5 115.7(19) . . . no C4 C5 H5 122.3(19) . . . 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 N4 C7 C8 -0.8(4) . . . . no C7 N4 C11 C10 0.4(4) . . . . no N6 N5 C12 O2 1.5(5) . . . . no N6 N5 C12 C9 -177.5(3) . . . . no C1 N1 C5 C4 0.4(4) . . . . no C5 N1 C1 C2 -0.8(4) . . . . no N3 N2 C6 C3 -179.3(3) . . . . no N3 N2 C6 O1 0.7(5) . . . . no N4 C7 C8 C9 0.2(4) . . . . no C7 C8 C9 C12 178.8(3) . . . . no C7 C8 C9 C10 0.7(4) . . . . no C10 C9 C12 N5 -154.7(3) . . . . no C12 C9 C10 C11 -179.3(3) . . . . no C8 C9 C12 O2 -151.9(3) . . . . no C8 C9 C10 C11 -1.1(4) . . . . no C10 C9 C12 O2 26.3(4) . . . . no C8 C9 C12 N5 27.2(4) . . . . no C9 C10 C11 N4 0.5(4) . . . . no C26 C20 C21 O8 5.7(4) . . . . no C26 C20 C25 C24 174.1(3) . . . . no C21 C20 C26 O6 1.2(4) . . . . no C21 C20 C25 C24 -3.5(4) . . . . no C25 C20 C26 O6 -176.4(3) . . . . no C25 C20 C26 O7 2.4(4) . . . . no C25 C20 C21 C22 3.6(4) . . . . no C21 C20 C26 O7 180.0(3) . . . . no C26 C20 C21 C22 -174.1(3) . . . . no C25 C20 C21 O8 -176.6(2) . . . . no O8 C21 C22 C23 180.0(2) . . . . no C20 C21 C22 C23 -0.3(4) . . . . no C21 C22 C23 C24 -3.4(4) . . . . no C21 C22 C23 N8 179.2(3) . . . . no C22 C23 C24 C25 3.5(4) . . . . no N8 C23 C24 C25 -179.0(3) . . . . no C23 C24 C25 C20 0.0(4) . . . . no C18 C13 C14 C15 0.7(4) . . . . no C19 C13 C18 C17 178.0(3) . . . . no C19 C13 C14 C15 -177.8(3) . . . . no C14 C13 C18 C17 -0.5(4) . . . . no C18 C13 C19 O3 171.7(3) . . . . no C18 C13 C19 O4 -8.6(4) . . . . no C19 C13 C14 O5 1.5(4) . . . . no C14 C13 C19 O4 169.8(3) . . . . no C18 C13 C14 O5 180.0(3) . . . . no C14 C13 C19 O3 -9.8(4) . . . . no C13 C14 C15 C16 0.3(4) . . . . no O5 C14 C15 C16 -179.0(3) . . . . no C14 C15 C16 N7 -179.6(3) . . . . no C14 C15 C16 C17 -1.5(4) . . . . no C15 C16 C17 C18 1.7(4) . . . . no N7 C16 C17 C18 179.8(3) . . . . no C16 C17 C18 C13 -0.7(4) . . . . no N1 C1 C2 C3 0.4(4) . . . . no C1 C2 C3 C4 0.4(4) . . . . no C1 C2 C3 C6 179.2(3) . . . . no C2 C3 C6 N2 25.7(4) . . . . no C4 C3 C6 O1 24.5(4) . . . . no C4 C3 C6 N2 -155.5(3) . . . . no C2 C3 C6 O1 -154.3(3) . . . . no C2 C3 C4 C5 -0.8(4) . . . . no C6 C3 C4 C5 -179.6(3) . . . . no C3 C4 C5 N1 0.4(4) . . . . 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 O1 N3 2.763(3) . . no O1 C7 3.356(4) . . no O1 O6 3.180(3) . . no O1 N6 3.015(4) . 3_554 no O2 N6 2.783(3) . . no O2 N3 3.044(4) . 3_545 no O2 O8 3.113(4) . 3_544 no O3 C1 3.325(3) . 2_654 no O3 O5 2.589(3) . . no O3 N8 3.057(3) . 1_544 no O4 N1 2.580(3) . 2_654 no O4 C1 3.401(3) . 2_654 no O5 O3 2.589(3) . . no O5 N5 3.033(3) . 1_554 no O6 N7 3.023(3) . 1_556 no O6 O1 3.180(3) . . no O6 O8 2.557(3) . . no O8 N2 3.021(3) . 2_665 no O8 O2 3.113(4) . 3_555 no O8 O6 2.557(3) . . no O1 H7 2.45(3) . . no O1 H3B 2.63(5) . . no O1 H4 2.58(3) . . no O1 H7B 2.90(4) . 1_556 no O1 H3A 2.62(5) . . no O1 H6B 2.16(4) . 3_554 no O2 H6B 2.72(4) . . no O2 H10 2.60(3) . . no O2 H3A 2.12(5) . 3_545 no O3 H8A 2.28(4) . 1_544 no O3 H1 2.65(3) . 2_654 no O3 H5O 1.73(3) . . no O4 H11 2.60(3) . 4_554 no O4 H18 2.45(3) . . no O5 H25 2.71(3) . 3_544 no O5 H5A 2.11(3) . 1_554 no O6 H7B 2.22(4) . 1_556 no O6 H8O 1.51(5) . . no O6 H6A 2.45(8) . 3_555 no O7 H25 2.38(3) . . no O7 H5 2.62(3) . 3_555 no O8 H3B 2.66(5) . . no O8 H2N 2.17(4) . 2_665 no O8 H17 2.89(3) . 2_665 no N1 O4 2.580(3) . 2_655 no N1 C19 3.321(4) . 2_655 no N2 O8 3.021(3) . 2_664 no N3 O2 3.044(4) . 3_554 no N3 O1 2.763(3) . . no N3 N7 3.100(4) . 2_665 no N5 O5 3.033(3) . 1_556 no N6 O2 2.783(3) . . no N6 N8 3.174(4) . 1_545 no N6 O1 3.015(4) . 3_545 no N7 N3 3.100(4) . 2_664 no N7 O6 3.023(3) . 1_554 no N8 C11 3.298(4) . 3_554 no N8 N6 3.174(4) . 1_565 no N8 O3 3.057(3) . 1_566 no N1 H4O 1.62(5) . 2_655 no N2 H2 2.70(3) . . no N3 H7A 2.15(3) . 2_665 no N5 H8 2.65(3) . . no N6 H8B 2.28(3) . 1_545 no N6 H24 2.94(3) . 1_545 no C1 O4 3.401(3) . 2_655 no C1 C13 3.338(4) . 1_556 no C1 C18 3.569(4) . 1_556 no C1 O3 3.325(3) . 2_655 no C2 C16 3.583(4) . 1_556 no C2 C17 3.549(4) . 1_556 no C2 C18 3.598(4) . 1_556 no C3 C15 3.444(4) . 1_556 no C3 C16 3.553(4) . 1_556 no C3 C17 3.434(4) . . no C4 C17 3.531(4) . . no C4 C25 3.571(4) . 3_544 no C4 C15 3.591(4) . 1_556 no C4 C16 3.596(4) . . no C5 C13 3.438(4) . . no C5 C18 3.569(4) . . no C5 C14 3.595(4) . 1_556 no C7 O1 3.356(4) . . no C7 C24 3.548(4) . 3_544 no C7 C23 3.429(4) . 3_544 no C8 C25 3.559(4) . 3_544 no C8 C15 3.598(4) . 1_556 no C8 C24 3.503(4) . 3_544 no C8 C23 3.495(4) . 3_544 no C9 C21 3.535(4) . 3_544 no C9 C22 3.564(4) . 3_544 no C10 C23 3.365(4) . 3_545 no C10 C22 3.447(4) . 3_545 no C10 C18 3.580(4) . 4_456 no C11 C23 3.358(4) . 3_545 no C11 N8 3.298(4) . 3_545 no C12 C21 3.495(4) . 3_544 no C13 C1 3.338(4) . 1_554 no C13 C5 3.438(4) . . no C14 C5 3.595(4) . 1_554 no C15 C25 3.541(4) . 3_544 no C15 C8 3.598(4) . 1_554 no C15 C3 3.444(4) . 1_554 no C15 C4 3.591(4) . 1_554 no C16 C2 3.583(4) . 1_554 no C16 C3 3.553(4) . 1_554 no C16 C4 3.596(4) . . no C17 C4 3.531(4) . . no C17 C2 3.549(4) . 1_554 no C17 C3 3.434(4) . . no C18 C1 3.569(4) . 1_554 no C18 C5 3.569(4) . . no C18 C2 3.598(4) . 1_554 no C18 C10 3.580(4) . 4_554 no C19 N1 3.321(4) . 2_654 no C21 C12 3.495(4) . 3_555 no C21 C9 3.535(4) . 3_555 no C22 C10 3.447(4) . 3_554 no C22 C9 3.564(4) . 3_555 no C23 C10 3.365(4) . 3_554 no C23 C8 3.495(4) . 3_555 no C23 C11 3.358(4) . 3_554 no C23 C7 3.429(4) . 3_555 no C24 C8 3.503(4) . 3_555 no C24 C7 3.548(4) . 3_555 no C25 C15 3.541(4) . 3_555 no C25 C4 3.571(4) . 3_555 no C25 C8 3.559(4) . 3_555 no C1 H4O 2.55(5) . 2_655 no C1 H22 2.89(4) . 2_664 no C2 H22 2.85(4) . 2_664 no C2 H2N 2.71(3) . . no C4 H25 3.05(3) . 3_544 no C5 H4O 2.59(5) . 2_655 no C7 H15 2.75(4) . 1_556 no C8 H5A 2.63(3) . . no C8 H15 2.66(4) . 1_556 no C10 H1 3.08(3) . 4_455 no C10 H2 3.07(3) . 4_455 no C11 H1 2.86(3) . 4_455 no C14 H25 2.82(3) . 3_544 no C15 H25 2.87(3) . 3_544 no C17 H10 2.92(3) . 4_554 no C18 H10 2.74(3) . 4_554 no C18 H22 3.09(4) . 2_664 no C19 H5O 2.31(4) . . no C22 H18 2.95(3) . 2_665 no C24 H4 2.98(4) . 3_555 no C25 H4 2.82(4) . 3_555 no C26 H8O 2.06(4) . . no C26 H6A 3.08(8) . 3_555 no H1 H4O 2.56(6) . 2_655 no H1 O3 2.65(3) . 2_655 no H1 C11 2.86(3) . 4_555 no H1 C10 3.08(3) . 4_555 no H2 N2 2.70(3) . . no H2 C10 3.07(3) . 4_555 no H2 H2N 2.35(5) . . no H2N C2 2.71(3) . . no H2N O8 2.17(4) . 2_664 no H2N H2 2.35(5) . . no H3A O1 2.62(5) . . no H3A O2 2.12(5) . 3_554 no H3B H7A 2.58(6) . 2_665 no H3B O1 2.63(5) . . no H3B H8O 2.57(7) . . no H3B O8 2.66(5) . . no H4 C24 2.98(4) . 3_544 no H4 O1 2.58(3) . . no H4 C25 2.82(4) . 3_544 no H4 H25 2.47(5) . 3_544 no H4O N1 1.62(5) . 2_654 no H4O H1 2.56(6) . 2_654 no H4O C5 2.59(5) . 2_654 no H4O C1 2.55(5) . 2_654 no H5 O7 2.62(3) . 3_544 no H5A O5 2.11(3) . 1_556 no H5A C8 2.63(3) . . no H5A H5O 2.53(5) . 1_556 no H5A H8 2.20(4) . . no H5O O3 1.73(3) . . no H5O C19 2.31(4) . . no H5O H5A 2.53(5) . 1_554 no H6A H8B 2.42(7) . 1_545 no H6A C26 3.08(8) . 3_544 no H6A H24 2.56(7) . 1_545 no H6A O6 2.45(8) . 3_544 no H6B O1 2.16(4) . 3_545 no H6B O2 2.72(4) . . no H7 H15 2.59(5) . 1_556 no H7 O1 2.45(3) . . no H7A N3 2.15(3) . 2_664 no H7A H17 2.40(5) . . no H7A H3B 2.58(6) . 2_664 no H7B H15 2.44(5) . . no H7B O6 2.22(4) . 1_554 no H7B O1 2.90(4) . 1_554 no H8 H15 2.55(5) . 1_556 no H8 N5 2.65(3) . . no H8 H5A 2.20(4) . . no H8A H22 2.39(5) . . no H8A O3 2.28(4) . 1_566 no H8B N6 2.28(3) . 1_565 no H8B H6A 2.42(7) . 1_565 no H8B H24 2.34(4) . . no H8O O6 1.51(5) . . no H8O H3B 2.57(7) . . no H8O C26 2.06(4) . . no H10 O2 2.60(3) . . no H10 C17 2.92(3) . 4_456 no H10 C18 2.74(3) . 4_456 no H10 H18 2.42(5) . 4_456 no H11 O4 2.60(3) . 4_456 no H15 C7 2.75(4) . 1_554 no H15 C8 2.66(4) . 1_554 no H15 H7 2.59(5) . 1_554 no H15 H7B 2.44(5) . . no H15 H8 2.55(5) . 1_554 no H17 O8 2.89(3) . 2_664 no H17 H7A 2.40(5) . . no H18 O4 2.45(3) . . no H18 C22 2.95(3) . 2_664 no H18 H22 2.40(5) . 2_664 no H18 H10 2.42(5) . 4_554 no H22 H8A 2.39(5) . . no H22 C1 2.89(4) . 2_665 no H22 C2 2.85(4) . 2_665 no H22 C18 3.09(4) . 2_665 no H22 H18 2.40(5) . 2_665 no H24 N6 2.94(3) . 1_565 no H24 H6A 2.56(7) . 1_565 no H24 H8B 2.34(4) . . no H25 O7 2.38(3) . . no H25 O5 2.71(3) . 3_555 no H25 C4 3.05(3) . 3_555 no H25 C14 2.82(3) . 3_555 no H25 C15 2.87(3) . 3_555 no H25 H4 2.47(5) . 3_555 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # N2 H2N O8 0.88(4) 2.17(4) 3.021(3) 164(4) 2_664 yes N3 H3A O2 1.01(5) 2.12(5) 3.044(4) 150(4) 3_554 yes O4 H4O N1 0.97(5) 1.62(5) 2.580(3) 173(5) 2_654 yes N5 H5A O5 0.94(3) 2.11(3) 3.033(3) 166(3) 1_556 yes O5 H5O O3 0.96(3) 1.73(3) 2.589(3) 148(3) . yes N6 H6A O6 0.96(8) 2.45(8) 3.270(4) 143(5) 3_544 yes N6 H6B O1 0.88(4) 2.16(4) 3.015(4) 162(3) 3_545 yes N7 H7A N3 0.97(3) 2.15(3) 3.100(4) 167(3) 2_664 yes N7 H7B O6 0.94(4) 2.22(4) 3.023(3) 143(3) 1_554 yes O7 H7O N4 1.18(5) 1.38(5) 2.559(3) 178(6) . yes N8 H8A O3 0.85(4) 2.28(4) 3.057(3) 152(3) 1_566 yes N8 H8B N6 0.90(3) 2.28(3) 3.174(4) 173(3) 1_565 yes O8 H8O O6 1.07(5) 1.51(5) 2.557(3) 165(4) . yes C7 H7 O1 0.91(3) 2.45(3) 3.356(4) 170(3) . yes C18 H18 O4 0.91(3) 2.45(3) 2.765(3) 101(2) . yes C25 H25 O7 1.01(3) 2.38(3) 2.786(3) 102.6(19) . yes #===END # Attachment 'web_deposit_cif_file_4_PawelGrobelny_1289286463.cif' # CIF-file generated for datam in Pna2(1) #=============================================================================== data_datam5 _database_code_depnum_ccdc_archive 'CCDC 800234' #TrackingRef 'web_deposit_cif_file_4_PawelGrobelny_1289286463.cif' #=============================================================================== _chemical_name_systematic ; ; _chemical_name_common 'Isoniazid:4-aminosalicylic acid co-crystal' _chemical_melting_point ? _chemical_formula_moiety 'C13 H14 N4 O4, C7 H7 N O3, C6 H7 N3 O' _chemical_formula_structural ? _chemical_formula_sum 'C26 H28 N8 O8' _chemical_formula_iupac ? _chemical_formula_weight 580.56 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_space_group_name_H-M 'P n a 21' _symmetry_Int_Tables_number 33 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,1/2+z 3 1/2-x,1/2+y,1/2+z 4 1/2+x,1/2-y,z _cell_length_a 21.889(2) _cell_length_b 16.5223(14) _cell_length_c 7.2750(6) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2631.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 6706 _cell_measurement_theta_min 1.9 _cell_measurement_theta_max 27.5 _cell_special_details ; ; _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.466 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 0.111 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.835 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' #=============================================================================== _exptl_special_details ; ; _diffrn_ambient_temperature 180(2) _diffrn_source_power 0.6 _diffrn_source_voltage 50.0 _diffrn_source_current 12.0 _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_source 'Sealed Tube' _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_measurement_specimen_support Fiber _diffrn_detector CCD _diffrn_measurement_device ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_detector_area_resol_mean 13.6612 _diffrn_measurement_method 'profile data from \w-scans' _diffrn_reflns_number 27155 _diffrn_reflns_av_R_equivalents 0.0496 _diffrn_reflns_av_sigmaI/netI 0.0227 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 27.50 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _reflns_number_total 3254 _reflns_number_gt 3056 _reflns_threshold_expression >2\s(I) _diffrn_measurement_details ; scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 0.0000 XTD: 49.4338 2theta: 29.5507 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 120.0000 XTD: 49.4338 2theta: 29.5507 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 240.0000 XTD: 49.4338 2theta: 29.5507 ; _diffrn_orient_matrix_UB_11 0.016231 _diffrn_orient_matrix_UB_12 -0.135466 _diffrn_orient_matrix_UB_13 0.016732 _diffrn_orient_matrix_UB_21 0.060034 _diffrn_orient_matrix_UB_22 0.007436 _diffrn_orient_matrix_UB_23 0.001965 _diffrn_orient_matrix_UB_31 -0.002145 _diffrn_orient_matrix_UB_32 0.005341 _diffrn_orient_matrix_UB_33 0.045321 _diffrn_orient_matrix_type d*Trek _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement ? _computing_molecular_graphics ? _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== _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^ > 2\s(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^)+(0.0711P)^2^+0.3080P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3254 _refine_ls_number_parameters 492 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0436 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.1172 _refine_ls_wR_factor_gt 0.1066 _refine_ls_goodness_of_fit_ref 1.141 _refine_ls_restrained_S_all 1.141 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.222 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.058 #=============================================================================== loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags O2 O Uani 0.11401(8) 0.10565(11) 0.9164(4) 1.000 0.0419(6) . . O6 O Uani 0.31681(9) 0.50696(11) 0.9854(4) 1.000 0.0416(6) . . O7 O Uani 0.22146(8) 0.53769(10) 0.9006(4) 1.000 0.0407(6) . . O8 O Uani 0.39834(8) 0.61786(13) 0.9901(3) 1.000 0.0403(6) . . N4 N Uani 0.20113(9) 0.38505(12) 0.9100(4) 1.000 0.0320(6) . . N5 N Uani 0.21564(10) 0.08100(12) 0.9307(4) 1.000 0.0338(6) . . N6 N Uani 0.21005(12) -0.00472(13) 0.9286(5) 1.000 0.0412(8) . . N8 N Uani 0.33218(11) 0.89240(13) 0.9191(4) 1.000 0.0396(7) . . C7 C Uani 0.24326(11) 0.33388(16) 0.8453(4) 1.000 0.0311(7) . . C8 C Uani 0.23507(11) 0.25025(15) 0.8474(4) 1.000 0.0283(7) . . C9 C Uani 0.18110(10) 0.21938(13) 0.9176(4) 1.000 0.0263(6) . . C10 C Uani 0.13690(10) 0.27273(16) 0.9816(4) 1.000 0.0291(7) . . C11 C Uani 0.14843(11) 0.35542(16) 0.9766(4) 1.000 0.0316(7) . . C12 C Uani 0.16706(10) 0.12986(14) 0.9219(4) 1.000 0.0293(7) . . C20 C Uani 0.29269(10) 0.64403(13) 0.9180(4) 1.000 0.0272(6) . . C21 C Uani 0.35252(10) 0.67124(15) 0.9541(4) 1.000 0.0300(7) . . C22 C Uani 0.36552(11) 0.75368(16) 0.9542(4) 1.000 0.0314(7) . . C23 C Uani 0.32033(11) 0.81076(14) 0.9173(4) 1.000 0.0300(7) . . C24 C Uani 0.26117(11) 0.78347(15) 0.8718(4) 1.000 0.0295(7) . . C25 C Uani 0.24850(11) 0.70204(14) 0.8726(4) 1.000 0.0277(7) . . C26 C Uani 0.27733(11) 0.55742(15) 0.9359(4) 1.000 0.0313(7) . . O3 O Uani 0.42400(8) 0.00270(10) 0.1152(4) 1.000 0.0433(7) . . O4 O Uani 0.52110(8) 0.03669(11) 0.1710(4) 1.000 0.0407(6) . . O5 O Uani 0.34704(8) 0.11690(12) 0.0369(3) 1.000 0.0368(6) . . N7 N Uani 0.40890(11) 0.38979(14) 0.1440(4) 1.000 0.0398(7) . . C13 C Uani 0.44912(10) 0.14149(14) 0.1483(4) 1.000 0.0277(6) . . C14 C Uani 0.39128(10) 0.16963(15) 0.0933(3) 1.000 0.0280(6) . . C15 C Uani 0.37823(10) 0.25163(15) 0.0916(4) 1.000 0.0290(7) . . C16 C Uani 0.42213(11) 0.30864(14) 0.1443(4) 1.000 0.0295(7) . . C17 C Uani 0.47996(11) 0.28078(15) 0.2044(4) 1.000 0.0303(7) . . C18 C Uani 0.49259(10) 0.19904(15) 0.2054(4) 1.000 0.0279(7) . . C19 C Uani 0.46364(11) 0.05464(15) 0.1441(4) 1.000 0.0323(7) . . O1 O Uani 0.37621(8) 0.39943(12) 0.6683(4) 1.000 0.0426(6) . . N1 N Uani 0.45664(9) 0.11636(13) 0.6592(3) 1.000 0.0325(6) . . N2 N Uani 0.47754(10) 0.42031(13) 0.6508(4) 1.000 0.0403(7) . . N3 N Uani 0.47308(12) 0.50606(14) 0.6515(6) 1.000 0.0484(8) . . C1 C Uani 0.50075(12) 0.16589(16) 0.7195(4) 1.000 0.0329(7) . . C2 C Uani 0.49499(11) 0.24929(15) 0.7237(4) 1.000 0.0304(7) . . C3 C Uani 0.44039(10) 0.28314(14) 0.6620(3) 1.000 0.0270(6) . . C4 C Uani 0.39418(11) 0.23230(17) 0.6015(4) 1.000 0.0311(7) . . C5 C Uani 0.40395(11) 0.14926(16) 0.6021(4) 1.000 0.0330(7) . . C6 C Uani 0.42825(11) 0.37307(15) 0.6600(4) 1.000 0.0311(7) . . H5N H Uiso 0.2534(18) 0.096(2) 0.953(6) 1.000 0.057(11) . . H6A H Uiso 0.191(2) -0.022(3) 0.817(7) 1.000 0.060(12) . . H6B H Uiso 0.186(2) -0.023(3) 1.019(7) 1.000 0.060(12) . . H7 H Uiso 0.2790(12) 0.3547(16) 0.801(4) 1.000 0.024(7) . . H7O H Uiso 0.210(3) 0.470(3) 0.910(10) 1.000 0.116(19) . . H8 H Uiso 0.2638(15) 0.220(2) 0.800(5) 1.000 0.038(9) . . H8A H Uiso 0.3653(19) 0.914(2) 0.969(6) 1.000 0.061(12) . . H8B H Uiso 0.2974(15) 0.9286(19) 0.910(5) 1.000 0.039(8) . . H8O H Uiso 0.3757(19) 0.572(2) 0.998(6) 1.000 0.064(12) . . H10 H Uiso 0.0992(14) 0.255(2) 1.042(5) 1.000 0.039(8) . . H11 H Uiso 0.1186(14) 0.3949(18) 1.029(5) 1.000 0.032(7) . . H22 H Uiso 0.4024(17) 0.773(2) 0.985(6) 1.000 0.053(10) . . H24 H Uiso 0.2287(18) 0.821(2) 0.851(6) 1.000 0.060(12) . . H25 H Uiso 0.2082(14) 0.6831(18) 0.845(5) 1.000 0.038(8) . . H4O H Uiso 0.532(2) -0.023(3) 0.161(8) 1.000 0.075(13) . . H5O H Uiso 0.3622(19) 0.069(2) 0.059(7) 1.000 0.068(12) . . H7A H Uiso 0.4386(16) 0.423(2) 0.150(6) 1.000 0.050(10) . . H7B H Uiso 0.375(2) 0.405(2) 0.078(7) 1.000 0.067(13) . . H15 H Uiso 0.3363(15) 0.2678(19) 0.054(5) 1.000 0.042(9) . . H17 H Uiso 0.5092(13) 0.3197(17) 0.239(4) 1.000 0.024(7) . . H18 H Uiso 0.5310(13) 0.1760(17) 0.253(4) 1.000 0.028(7) . . H1 H Uiso 0.5383(14) 0.1333(19) 0.759(5) 1.000 0.041(9) . . H2 H Uiso 0.5274(16) 0.284(2) 0.764(5) 1.000 0.049(10) . . H2N H Uiso 0.5161(17) 0.402(2) 0.642(6) 1.000 0.053(10) . . H3A H Uiso 0.4447(19) 0.522(3) 0.557(6) 1.000 0.052(10) . . H3B H Uiso 0.455(3) 0.518(4) 0.767(10) 1.000 0.10(2) . . H4 H Uiso 0.3557(16) 0.255(2) 0.566(5) 1.000 0.047(10) . . H5 H Uiso 0.3716(14) 0.1120(18) 0.563(5) 1.000 0.032(7) . . 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 O2 0.0258(9) 0.0332(9) 0.0668(13) 0.0035(10) -0.0028(10) -0.0072(7) O6 0.0336(9) 0.0282(9) 0.0630(13) -0.0007(9) -0.0058(10) 0.0069(7) O7 0.0309(9) 0.0254(8) 0.0658(13) 0.0032(9) -0.0070(10) -0.0024(6) O8 0.0219(8) 0.0411(10) 0.0579(13) 0.0047(10) -0.0017(9) 0.0037(7) N4 0.0297(10) 0.0267(10) 0.0397(11) 0.0010(10) -0.0034(10) -0.0032(8) N5 0.0275(10) 0.0231(9) 0.0508(14) -0.0026(10) -0.0056(10) -0.0031(8) N6 0.0422(13) 0.0223(10) 0.0591(16) -0.0002(12) -0.0047(13) -0.0033(8) N8 0.0379(12) 0.0293(10) 0.0516(14) -0.0027(11) -0.0018(12) -0.0101(9) C7 0.0238(11) 0.0317(12) 0.0377(13) 0.0029(11) 0.0009(10) -0.0042(9) C8 0.0253(11) 0.0283(13) 0.0314(14) -0.0015(10) 0.0004(10) 0.0004(9) C9 0.0243(10) 0.0259(10) 0.0286(11) -0.0007(10) -0.0050(9) -0.0036(8) C10 0.0199(10) 0.0320(12) 0.0353(13) -0.0013(10) -0.0021(10) -0.0018(9) C11 0.0247(11) 0.0311(11) 0.0389(13) -0.0016(11) -0.0027(10) 0.0014(9) C12 0.0268(11) 0.0275(11) 0.0335(12) 0.0000(11) -0.0021(10) -0.0019(9) C20 0.0219(10) 0.0285(11) 0.0313(11) -0.0023(10) 0.0011(9) -0.0004(8) C21 0.0213(10) 0.0370(12) 0.0316(12) 0.0017(11) 0.0024(9) 0.0022(9) C22 0.0238(10) 0.0377(13) 0.0327(12) 0.0006(11) 0.0002(10) -0.0078(9) C23 0.0300(11) 0.0318(12) 0.0283(11) -0.0018(10) 0.0019(10) -0.0075(9) C24 0.0255(11) 0.0283(12) 0.0347(14) -0.0009(11) -0.0008(10) -0.0014(9) C25 0.0224(11) 0.0270(11) 0.0338(14) -0.0011(10) -0.0016(10) -0.0010(8) C26 0.0281(12) 0.0285(12) 0.0374(13) -0.0022(11) 0.0004(10) 0.0023(9) O3 0.0291(9) 0.0288(9) 0.0719(15) -0.0048(10) -0.0042(10) -0.0047(7) O4 0.0261(8) 0.0285(8) 0.0674(14) 0.0003(10) -0.0035(10) 0.0004(7) O5 0.0234(8) 0.0335(9) 0.0536(12) -0.0015(9) -0.0073(9) -0.0061(7) N7 0.0338(12) 0.0277(10) 0.0580(16) -0.0007(11) -0.0055(12) 0.0001(9) C13 0.0243(10) 0.0276(11) 0.0312(11) -0.0015(10) 0.0009(10) -0.0029(9) C14 0.0222(10) 0.0330(12) 0.0287(11) -0.0014(10) 0.0004(9) -0.0053(9) C15 0.0210(10) 0.0338(13) 0.0323(13) 0.0023(10) -0.0015(10) -0.0016(9) C16 0.0284(11) 0.0295(11) 0.0305(12) 0.0004(10) 0.0015(10) -0.0007(9) C17 0.0257(11) 0.0311(12) 0.0342(13) -0.0025(11) -0.0011(10) -0.0056(9) C18 0.0220(10) 0.0328(12) 0.0289(12) -0.0006(10) -0.0016(10) -0.0024(9) C19 0.0266(11) 0.0311(12) 0.0391(13) -0.0011(11) -0.0014(11) -0.0015(9) O1 0.0246(8) 0.0375(10) 0.0658(14) 0.0058(10) 0.0065(10) 0.0044(7) N1 0.0279(10) 0.0302(10) 0.0394(12) 0.0027(10) 0.0000(9) -0.0006(8) N2 0.0255(10) 0.0278(10) 0.0675(17) 0.0027(12) 0.0047(12) 0.0018(8) N3 0.0354(11) 0.0257(11) 0.084(2) 0.0037(14) 0.0020(15) -0.0010(9) C1 0.0279(11) 0.0335(12) 0.0373(13) 0.0051(11) -0.0009(10) 0.0003(9) C2 0.0243(11) 0.0344(13) 0.0324(14) 0.0001(11) -0.0008(10) 0.0000(9) C3 0.0226(10) 0.0315(12) 0.0270(11) 0.0008(10) 0.0028(9) 0.0002(8) C4 0.0211(10) 0.0389(13) 0.0333(12) 0.0003(11) 0.0011(10) 0.0014(9) C5 0.0259(12) 0.0334(12) 0.0396(14) -0.0018(12) 0.0006(10) -0.0037(10) C6 0.0257(11) 0.0298(11) 0.0377(13) 0.0025(12) 0.0050(10) 0.0034(9) #=============================================================================== _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; 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 O2 C12 1.229(3) . . yes O6 C26 1.254(3) . . yes O7 C26 1.291(3) . . yes O8 C21 1.361(3) . . yes O7 H7O 1.15(5) . . no O8 H8O 0.91(4) . . no O3 C19 1.238(3) . . yes O4 C19 1.307(3) . . yes O5 C14 1.366(3) . . yes O4 H4O 1.02(5) . . no O5 H5O 0.87(4) . . no O1 C6 1.221(3) . . yes N4 C7 1.337(3) . . yes N4 C11 1.344(3) . . yes N5 N6 1.422(3) . . yes N5 C12 1.337(3) . . yes N8 C23 1.374(3) . . yes N4 H7O 1.42(5) . . no N5 H5N 0.88(4) . . no N6 H6A 0.96(5) . . no N6 H6B 0.90(5) . . no N8 H8A 0.89(4) . . no N8 H8B 0.97(3) . . no N7 C16 1.372(3) . . yes N7 H7B 0.92(4) . . no N7 H7A 0.85(3) . . no N1 C5 1.341(3) . . yes N1 C1 1.340(3) . . yes N2 C6 1.333(3) . . yes N2 N3 1.420(3) . . yes N2 H2N 0.90(4) . . no N3 H3A 0.96(4) . . no N3 H3B 0.95(7) . . no C7 C8 1.393(4) . . no C8 C9 1.384(3) . . no C9 C10 1.389(3) . . no C9 C12 1.511(3) . . no C10 C11 1.390(4) . . no C20 C25 1.401(3) . . no C20 C26 1.476(3) . . no C20 C21 1.409(3) . . no C21 C22 1.392(4) . . no C22 C23 1.393(3) . . no C23 C24 1.411(3) . . no C24 C25 1.374(3) . . no C7 H7 0.91(3) . . no C8 H8 0.87(3) . . no C10 H10 0.98(3) . . no C11 H11 1.00(3) . . no C22 H22 0.90(4) . . no C24 H24 0.96(4) . . no C25 H25 0.96(3) . . no C13 C14 1.407(3) . . no C13 C19 1.470(3) . . no C13 C18 1.408(3) . . no C14 C15 1.385(3) . . no C15 C16 1.399(3) . . no C16 C17 1.416(3) . . no C17 C18 1.379(3) . . no C15 H15 0.99(3) . . no C17 H17 0.94(3) . . no C18 H18 0.99(3) . . no C1 C2 1.384(4) . . no C2 C3 1.394(3) . . no C3 C4 1.387(3) . . no C3 C6 1.510(3) . . no C4 C5 1.389(4) . . no C1 H1 1.02(3) . . no C2 H2 0.96(4) . . no C4 H4 0.96(3) . . no C5 H5 0.98(3) . . 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 C26 O7 H7O 116(3) . . . no C21 O8 H8O 99(3) . . . no C19 O4 H4O 116(2) . . . no C14 O5 H5O 105(3) . . . no C7 N4 C11 119.3(2) . . . yes N6 N5 C12 122.2(2) . . . yes C11 N4 H7O 119(3) . . . no C7 N4 H7O 122(3) . . . no C12 N5 H5N 126(2) . . . no N6 N5 H5N 111(2) . . . no H6A N6 H6B 106(4) . . . no N5 N6 H6B 112(3) . . . no N5 N6 H6A 110(3) . . . no H8A N8 H8B 115(3) . . . no C23 N8 H8B 117.2(19) . . . no C23 N8 H8A 124(2) . . . no C16 N7 H7A 118(2) . . . no H7A N7 H7B 118(3) . . . no C16 N7 H7B 116(2) . . . no C1 N1 C5 118.3(2) . . . yes N3 N2 C6 121.9(2) . . . yes C6 N2 H2N 125(2) . . . no N3 N2 H2N 114(2) . . . no N2 N3 H3B 104(4) . . . no N2 N3 H3A 108(3) . . . no H3A N3 H3B 108(5) . . . no N4 C7 C8 122.3(2) . . . yes C7 C8 C9 118.6(2) . . . no C8 C9 C12 122.8(2) . . . no C10 C9 C12 118.2(2) . . . no C8 C9 C10 119.0(2) . . . no C9 C10 C11 119.2(2) . . . no N4 C11 C10 121.6(2) . . . yes O2 C12 N5 123.8(2) . . . yes O2 C12 C9 120.7(2) . . . yes N5 C12 C9 115.49(19) . . . yes C25 C20 C26 121.8(2) . . . no C21 C20 C26 120.3(2) . . . no C21 C20 C25 117.9(2) . . . no O8 C21 C22 118.9(2) . . . yes O8 C21 C20 120.9(2) . . . yes C20 C21 C22 120.2(2) . . . no C21 C22 C23 121.2(2) . . . no N8 C23 C22 121.9(2) . . . yes C22 C23 C24 118.7(2) . . . no N8 C23 C24 119.3(2) . . . yes C23 C24 C25 119.8(2) . . . no C20 C25 C24 122.1(2) . . . no O6 C26 C20 120.9(2) . . . yes O7 C26 C20 116.3(2) . . . yes O6 C26 O7 122.8(2) . . . yes C8 C7 H7 119.2(17) . . . no N4 C7 H7 118.5(17) . . . no C7 C8 H8 118(2) . . . no C9 C8 H8 123(2) . . . no C11 C10 H10 117(2) . . . no C9 C10 H10 123(2) . . . no C10 C11 H11 120.9(18) . . . no N4 C11 H11 117.5(18) . . . no C21 C22 H22 122(2) . . . no C23 C22 H22 117(2) . . . no C23 C24 H24 121(2) . . . no C25 C24 H24 119(2) . . . no C20 C25 H25 117.5(18) . . . no C24 C25 H25 120.4(18) . . . no C14 C13 C18 118.0(2) . . . no C14 C13 C19 120.8(2) . . . no C18 C13 C19 121.3(2) . . . no O5 C14 C13 120.9(2) . . . yes C13 C14 C15 120.8(2) . . . no O5 C14 C15 118.4(2) . . . yes C14 C15 C16 121.0(2) . . . no C15 C16 C17 118.7(2) . . . no N7 C16 C15 120.8(2) . . . yes N7 C16 C17 120.5(2) . . . yes C16 C17 C18 120.0(2) . . . no C13 C18 C17 121.6(2) . . . no O3 C19 O4 122.9(2) . . . yes O4 C19 C13 115.2(2) . . . yes O3 C19 C13 121.9(2) . . . yes C16 C15 H15 121.9(18) . . . no C14 C15 H15 117.1(18) . . . no C16 C17 H17 117.9(17) . . . no C18 C17 H17 122.1(17) . . . no C13 C18 H18 114.8(17) . . . no C17 C18 H18 123.5(17) . . . no N1 C1 C2 123.4(2) . . . yes C1 C2 C3 118.1(2) . . . no C2 C3 C4 119.0(2) . . . no C4 C3 C6 117.7(2) . . . no C2 C3 C6 123.3(2) . . . no C3 C4 C5 119.0(2) . . . no N1 C5 C4 122.3(2) . . . yes O1 C6 C3 121.0(2) . . . yes N2 C6 C3 115.7(2) . . . yes O1 C6 N2 123.3(2) . . . yes N1 C1 H1 110.4(18) . . . no C2 C1 H1 126.2(18) . . . no C1 C2 H2 122(2) . . . no C3 C2 H2 120(2) . . . no C3 C4 H4 119(2) . . . no C5 C4 H4 122(2) . . . no N1 C5 H5 117.2(18) . . . no C4 C5 H5 120.6(18) . . . 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 N4 C7 C8 -1.2(4) . . . . no C7 N4 C11 C10 0.7(4) . . . . no N6 N5 C12 O2 2.1(5) . . . . no N6 N5 C12 C9 -177.5(3) . . . . no C1 N1 C5 C4 0.8(4) . . . . no C5 N1 C1 C2 -0.8(4) . . . . no N3 N2 C6 C3 -178.7(3) . . . . no N3 N2 C6 O1 0.5(5) . . . . no N4 C7 C8 C9 0.6(4) . . . . no C7 C8 C9 C12 178.5(3) . . . . no C7 C8 C9 C10 0.6(4) . . . . no C10 C9 C12 N5 -154.5(3) . . . . no C12 C9 C10 C11 -179.1(3) . . . . no C8 C9 C12 O2 -151.9(3) . . . . no C8 C9 C10 C11 -1.2(4) . . . . no C10 C9 C12 O2 25.9(4) . . . . no C8 C9 C12 N5 27.7(4) . . . . no C9 C10 C11 N4 0.5(4) . . . . no C26 C20 C21 O8 5.8(4) . . . . no C26 C20 C25 C24 174.0(3) . . . . no C21 C20 C26 O6 0.9(4) . . . . no C21 C20 C25 C24 -3.4(4) . . . . no C25 C20 C26 O6 -176.5(3) . . . . no C25 C20 C26 O7 2.5(4) . . . . no C25 C20 C21 C22 3.6(4) . . . . no C21 C20 C26 O7 179.9(3) . . . . no C26 C20 C21 C22 -173.9(3) . . . . no C25 C20 C21 O8 -176.7(3) . . . . no O8 C21 C22 C23 179.7(3) . . . . no C20 C21 C22 C23 -0.6(4) . . . . no C21 C22 C23 C24 -2.6(4) . . . . no C21 C22 C23 N8 179.2(3) . . . . no C22 C23 C24 C25 2.9(4) . . . . no N8 C23 C24 C25 -178.9(3) . . . . no C23 C24 C25 C20 0.2(4) . . . . no C18 C13 C14 C15 1.5(4) . . . . no C19 C13 C18 C17 178.0(3) . . . . no C19 C13 C14 C15 -177.9(3) . . . . no C14 C13 C18 C17 -1.4(4) . . . . no C18 C13 C19 O3 171.4(3) . . . . no C18 C13 C19 O4 -9.3(4) . . . . no C19 C13 C14 O5 0.8(4) . . . . no C14 C13 C19 O4 170.0(3) . . . . no C18 C13 C14 O5 -179.8(2) . . . . no C14 C13 C19 O3 -9.3(4) . . . . no C13 C14 C15 C16 0.0(4) . . . . no O5 C14 C15 C16 -178.7(2) . . . . no C14 C15 C16 N7 -179.4(3) . . . . no C14 C15 C16 C17 -1.7(4) . . . . no C15 C16 C17 C18 1.7(4) . . . . no N7 C16 C17 C18 179.5(3) . . . . no C16 C17 C18 C13 -0.2(4) . . . . no N1 C1 C2 C3 0.1(4) . . . . no C1 C2 C3 C4 0.8(4) . . . . no C1 C2 C3 C6 179.8(2) . . . . no C2 C3 C6 N2 25.2(4) . . . . no C4 C3 C6 O1 25.0(4) . . . . no C4 C3 C6 N2 -155.8(3) . . . . no C2 C3 C6 O1 -154.1(3) . . . . no C2 C3 C4 C5 -0.8(4) . . . . no C6 C3 C4 C5 -179.9(2) . . . . no C3 C4 C5 N1 0.0(4) . . . . 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 O1 N3 2.760(3) . . no O1 N6 3.019(4) . 3_554 no O1 O6 3.189(4) . . no O1 C7 3.362(3) . . no O2 N6 2.784(3) . . no O2 N3 3.044(4) . 3_545 no O2 O8 3.120(4) . 3_544 no O3 O5 2.593(3) . . no O3 C1 3.324(3) . 2_654 no O3 N8 3.065(3) . 1_544 no O4 N1 2.577(3) . 2_654 no O4 C1 3.399(3) . 2_654 no O5 N5 3.037(3) . 1_554 no O5 O3 2.593(3) . . no O6 N7 3.024(3) . 1_556 no O6 O8 2.558(3) . . no O6 O1 3.189(4) . . no O8 O2 3.120(4) . 3_555 no O8 O6 2.558(3) . . no O8 N2 3.024(3) . 2_665 no O1 H3B 2.71(7) . . no O1 H6B 2.16(5) . 3_554 no O1 H4 2.54(3) . . no O1 H3A 2.65(5) . . no O1 H7 2.45(3) . . no O2 H2 2.85(3) . 4_455 no O2 H6B 2.75(5) . . no O2 H3A 2.15(5) . 3_545 no O2 H6A 2.80(5) . . no O2 H10 2.65(3) . . no O3 H8A 2.22(4) . 1_544 no O3 H1 2.61(3) . 2_654 no O3 H5O 1.79(4) . . no O4 H11 2.63(3) . 4_554 no O4 H18 2.39(3) . . no O5 H25 2.77(3) . 3_544 no O5 H5N 2.17(4) . 1_554 no O6 H6A 2.47(5) . 3_555 no O6 H8O 1.68(4) . . no O6 H7B 2.22(4) . 1_556 no O7 H25 2.45(3) . . no O7 H5 2.66(3) . 3_555 no O8 H17 2.92(3) . 2_665 no O8 H2N 2.20(4) . 2_665 no O8 H3B 2.63(7) . . no N1 C19 3.323(3) . 2_655 no N1 O4 2.577(3) . 2_655 no N2 O8 3.024(3) . 2_664 no N3 O1 2.760(3) . . no N3 O2 3.044(4) . 3_554 no N3 N7 3.105(3) . 2_665 no N5 O5 3.037(3) . 1_556 no N6 O1 3.019(4) . 3_545 no N6 O2 2.784(3) . . no N6 N8 3.169(3) . 1_545 no N7 N3 3.105(3) . 2_664 no N7 O6 3.024(3) . 1_554 no N8 O3 3.065(3) . 1_566 no N8 C11 3.304(4) . 3_554 no N8 N6 3.169(3) . 1_565 no N1 H4O 1.56(5) . 2_655 no N2 H2 2.64(3) . . no N3 H7A 2.26(3) . 2_665 no N5 H8 2.70(3) . . no N6 H8B 2.21(3) . 1_545 no N7 H6A 2.91(5) . 3_554 no C1 O3 3.324(3) . 2_655 no C1 O4 3.399(3) . 2_655 no C1 C13 3.342(4) . 1_556 no C1 C18 3.582(4) . 1_556 no C2 C16 3.587(4) . 1_556 no C2 C17 3.551(4) . 1_556 no C3 C16 3.557(4) . 1_556 no C3 C17 3.440(4) . . no C3 C15 3.448(4) . 1_556 no C4 C15 3.597(4) . 1_556 no C4 C17 3.537(4) . . no C4 C25 3.575(4) . 3_544 no C5 C14 3.600(4) . 1_556 no C5 C13 3.449(4) . . no C5 C18 3.574(4) . . no C7 C24 3.545(4) . 3_544 no C7 C23 3.432(4) . 3_544 no C7 O1 3.362(3) . . no C8 C25 3.563(4) . 3_544 no C8 C24 3.504(4) . 3_544 no C8 C23 3.502(4) . 3_544 no C9 C22 3.568(4) . 3_544 no C9 C21 3.542(4) . 3_544 no C10 C18 3.584(3) . 4_456 no C10 C23 3.364(4) . 3_545 no C10 C22 3.453(4) . 3_545 no C11 C23 3.360(4) . 3_545 no C11 N8 3.304(4) . 3_545 no C12 C21 3.498(4) . 3_544 no C13 C1 3.342(4) . 1_554 no C13 C5 3.449(4) . . no C14 C5 3.600(4) . 1_554 no C15 C25 3.542(4) . 3_544 no C15 C4 3.597(4) . 1_554 no C15 C3 3.448(4) . 1_554 no C16 C2 3.587(4) . 1_554 no C16 C3 3.557(4) . 1_554 no C17 C4 3.537(4) . . no C17 C3 3.440(4) . . no C17 C2 3.551(4) . 1_554 no C18 C10 3.584(3) . 4_554 no C18 C5 3.574(4) . . no C18 C1 3.582(4) . 1_554 no C19 N1 3.323(3) . 2_654 no C21 C12 3.498(4) . 3_555 no C21 C9 3.542(4) . 3_555 no C22 C10 3.453(4) . 3_554 no C22 C9 3.568(4) . 3_555 no C23 C11 3.360(4) . 3_554 no C23 C10 3.364(4) . 3_554 no C23 C8 3.502(4) . 3_555 no C23 C7 3.432(4) . 3_555 no C24 C7 3.545(4) . 3_555 no C24 C8 3.504(4) . 3_555 no C25 C4 3.575(4) . 3_555 no C25 C8 3.563(4) . 3_555 no C25 C15 3.542(4) . 3_555 no C1 H4O 2.50(5) . 2_655 no C1 H22 2.90(4) . 2_664 no C2 H22 2.86(4) . 2_664 no C2 H2N 2.63(3) . . no C4 H25 3.03(3) . 3_544 no C5 H4O 2.55(5) . 2_655 no C7 H15 2.77(3) . 1_556 no C8 H5N 2.69(3) . . no C8 H15 2.69(3) . 1_556 no C10 H2 3.02(4) . 4_455 no C11 H1 2.89(3) . 4_455 no C14 H25 2.85(3) . 3_544 no C15 H25 2.87(3) . 3_544 no C17 H10 2.93(3) . 4_554 no C18 H10 2.73(3) . 4_554 no C19 H5O 2.32(4) . . no C22 H18 2.94(3) . 2_665 no C22 H10 3.10(4) . 3_554 no C24 H4 2.96(4) . 3_555 no C25 H4 2.82(4) . 3_555 no C26 H8O 2.21(4) . . no H1 C11 2.89(3) . 4_555 no H1 H4O 2.49(6) . 2_655 no H1 O3 2.61(3) . 2_655 no H2 C10 3.02(4) . 4_555 no H2 N2 2.64(3) . . no H2 O2 2.85(3) . 4_555 no H2 H2N 2.16(5) . . no H2N H2 2.16(5) . . no H2N O8 2.20(4) . 2_664 no H2N C2 2.63(3) . . no H3A O1 2.65(5) . . no H3A O2 2.15(5) . 3_554 no H3B H8O 2.58(8) . . no H3B O8 2.63(7) . . no H3B O1 2.71(7) . . no H4 O1 2.54(3) . . no H4 C24 2.96(4) . 3_544 no H4 H25 2.44(5) . 3_544 no H4 C25 2.82(4) . 3_544 no H4O H1 2.49(6) . 2_654 no H4O C5 2.55(5) . 2_654 no H4O C1 2.50(5) . 2_654 no H4O N1 1.56(5) . 2_654 no H5 O7 2.66(3) . 3_544 no H5N O5 2.17(4) . 1_556 no H5N H5O 2.54(6) . 1_556 no H5N C8 2.69(3) . . no H5N H8 2.34(5) . . no H5O O3 1.79(4) . . no H5O H5N 2.54(6) . 1_554 no H5O C19 2.32(4) . . no H6A O6 2.47(5) . 3_544 no H6A O2 2.80(5) . . no H6A N7 2.91(5) . 3_545 no H6A H8B 2.56(6) . 1_545 no H6A H7B 2.56(7) . 3_545 no H6B O2 2.75(5) . . no H6B O1 2.16(5) . 3_545 no H7 O1 2.45(3) . . no H7A H17 2.39(4) . . no H7A N3 2.26(3) . 2_664 no H7B O6 2.22(4) . 1_554 no H7B H15 2.43(5) . . no H7B H6A 2.56(7) . 3_554 no H8 N5 2.70(3) . . no H8 H5N 2.34(5) . . no H8 H15 2.56(5) . 1_556 no H8A O3 2.22(4) . 1_566 no H8A H22 2.47(5) . . no H8B H6A 2.56(6) . 1_565 no H8B N6 2.21(3) . 1_565 no H8B H24 2.37(5) . . no H8O O6 1.68(4) . . no H8O C26 2.21(4) . . no H8O H3B 2.58(8) . . no H10 H18 2.43(4) . 4_456 no H10 C22 3.10(4) . 3_545 no H10 C18 2.73(3) . 4_456 no H10 O2 2.65(3) . . no H10 C17 2.93(3) . 4_456 no H11 O4 2.63(3) . 4_456 no H15 H7B 2.43(5) . . no H15 C8 2.69(3) . 1_554 no H15 C7 2.77(3) . 1_554 no H15 H8 2.56(5) . 1_554 no H17 O8 2.92(3) . 2_664 no H17 H7A 2.39(4) . . no H18 H10 2.43(4) . 4_554 no H18 O4 2.39(3) . . no H18 H22 2.38(5) . 2_664 no H18 C22 2.94(3) . 2_664 no H22 H18 2.38(5) . 2_665 no H22 C2 2.86(4) . 2_665 no H22 C1 2.90(4) . 2_665 no H22 H8A 2.47(5) . . no H24 H8B 2.37(5) . . no H25 O5 2.77(3) . 3_555 no H25 C4 3.03(3) . 3_555 no H25 C15 2.87(3) . 3_555 no H25 H4 2.44(5) . 3_555 no H25 C14 2.85(3) . 3_555 no H25 O7 2.45(3) . . no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # N2 H2N O8 0.90(4) 2.20(4) 3.024(3) 152(4) 2_664 yes N3 H3A O2 0.96(4) 2.15(5) 3.044(4) 154(4) 3_554 yes O4 H4O N1 1.02(5) 1.56(5) 2.577(3) 174(4) 2_654 yes N5 H5N O5 0.88(4) 2.17(4) 3.037(3) 171(3) 1_556 yes O5 H5O O3 0.87(4) 1.79(4) 2.593(3) 152(4) . yes N6 H6A O6 0.96(5) 2.47(5) 3.283(5) 143(4) 3_544 yes N6 H6B O1 0.90(5) 2.16(5) 3.019(4) 160(5) 3_545 yes N7 H7A N3 0.85(3) 2.26(3) 3.105(3) 171(3) 2_664 yes N7 H7B O6 0.92(4) 2.22(4) 3.024(3) 146(3) 1_554 yes O7 H7O N4 1.15(5) 1.42(5) 2.562(3) 174(6) . yes N8 H8A O3 0.89(4) 2.22(4) 3.065(3) 159(3) 1_566 yes N8 H8B N6 0.97(3) 2.21(3) 3.169(3) 169(3) 1_565 yes O8 H8O O6 0.91(4) 1.68(4) 2.558(3) 162(4) . yes C7 H7 O1 0.91(3) 2.45(3) 3.362(3) 175(3) . yes C18 H18 O4 0.99(3) 2.39(3) 2.765(3) 102.0(19) . yes C25 H25 O7 0.96(3) 2.45(3) 2.787(3) 100(2) . yes #===END # Attachment 'web_deposit_cif_file_5_PawelGrobelny_1289286463.cif' # CIF-file generated for datam in Pna2(1) #=============================================================================== data_datam6 _database_code_depnum_ccdc_archive 'CCDC 800235' #TrackingRef 'web_deposit_cif_file_5_PawelGrobelny_1289286463.cif' #=============================================================================== _chemical_name_systematic ; ; _chemical_name_common 'Isoniazid:4-aminosalicylic acid co-crystal' _chemical_melting_point ? _chemical_formula_moiety 'C13 H14 N4 O4, C7 H7 N O3, C6 H7 N3 O' _chemical_formula_structural ? _chemical_formula_sum 'C26 H28 N8 O8 ' _chemical_formula_iupac ? _chemical_formula_weight 580.56 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_space_group_name_H-M 'P n a 21' _symmetry_Int_Tables_number 33 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,1/2+z 3 1/2-x,1/2+y,1/2+z 4 1/2+x,1/2-y,z _cell_length_a 21.893(10) _cell_length_b 16.515(7) _cell_length_c 7.283(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2633(2) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 6526 _cell_measurement_theta_min 1.9 _cell_measurement_theta_max 27.5 _cell_special_details ; ; _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.465 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 0.111 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.785 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' #=============================================================================== _diffrn_ambient_temperature 200(2) _diffrn_source_power 0.6 _diffrn_source_voltage 50.0 _diffrn_source_current 12.0 _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_source 'Sealed Tube' _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_measurement_specimen_support Fiber _diffrn_detector CCD _diffrn_measurement_device ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_detector_area_resol_mean 13.6612 _diffrn_measurement_method 'profile data from \w-scans' _diffrn_reflns_number 27060 _diffrn_reflns_av_R_equivalents 0.0519 _diffrn_reflns_av_sigmaI/netI 0.0237 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 27.46 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.999 _reflns_number_total 3253 _reflns_number_gt 3065 _reflns_threshold_expression >2\s(I) _diffrn_measurement_details ; scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 0.0000 XTD: 49.3944 2theta: 29.5574 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 120.0000 XTD: 49.3944 2theta: 29.5574 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 240.0000 XTD: 49.3944 2theta: 29.5574 ; _diffrn_orient_matrix_UB_11 0.015039 _diffrn_orient_matrix_UB_12 -0.135415 _diffrn_orient_matrix_UB_13 0.017060 _diffrn_orient_matrix_UB_21 0.060096 _diffrn_orient_matrix_UB_22 0.006984 _diffrn_orient_matrix_UB_23 0.002457 _diffrn_orient_matrix_UB_31 -0.002482 _diffrn_orient_matrix_UB_32 0.005430 _diffrn_orient_matrix_UB_33 0.045285 _diffrn_orient_matrix_type d*Trek _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement ? _computing_molecular_graphics ? _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== _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^ > 2\s(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^)+(0.0744P)^2^+0.2927P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3253 _refine_ls_number_parameters 492 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0463 _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_ref 0.1243 _refine_ls_wR_factor_gt 0.1137 _refine_ls_goodness_of_fit_ref 1.162 _refine_ls_restrained_S_all 1.161 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.212 _refine_diff_density_min -0.190 _refine_diff_density_rms 0.058 #=============================================================================== loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags O2 O Uani 0.11404(9) 0.10605(12) 0.9166(4) 1.000 0.0462(7) . . O6 O Uani 0.31697(9) 0.50730(12) 0.9845(4) 1.000 0.0453(7) . . O7 O Uani 0.22146(8) 0.53810(11) 0.9012(4) 1.000 0.0447(7) . . O8 O Uani 0.39837(8) 0.61792(14) 0.9900(3) 1.000 0.0436(7) . . N4 N Uani 0.20111(10) 0.38525(13) 0.9099(4) 1.000 0.0345(6) . . N5 N Uani 0.21544(10) 0.08145(13) 0.9311(4) 1.000 0.0368(7) . . N6 N Uani 0.20981(13) -0.00458(14) 0.9292(5) 1.000 0.0448(9) . . N8 N Uani 0.33219(12) 0.89256(14) 0.9194(4) 1.000 0.0423(8) . . C7 C Uani 0.24317(12) 0.33400(16) 0.8454(4) 1.000 0.0337(7) . . C8 C Uani 0.23489(12) 0.25039(16) 0.8474(4) 1.000 0.0312(8) . . C9 C Uani 0.18101(11) 0.21972(13) 0.9179(4) 1.000 0.0280(7) . . C10 C Uani 0.13699(11) 0.27275(16) 0.9816(4) 1.000 0.0309(7) . . C11 C Uani 0.14864(11) 0.35567(16) 0.9762(4) 1.000 0.0337(7) . . C12 C Uani 0.16709(11) 0.12993(15) 0.9221(4) 1.000 0.0316(7) . . C20 C Uani 0.29269(10) 0.64430(14) 0.9174(4) 1.000 0.0296(7) . . C21 C Uani 0.35246(11) 0.67171(16) 0.9537(4) 1.000 0.0313(7) . . C22 C Uani 0.36544(12) 0.75410(17) 0.9544(4) 1.000 0.0343(8) . . C23 C Uani 0.32018(11) 0.81151(15) 0.9178(4) 1.000 0.0326(7) . . C24 C Uani 0.26095(12) 0.78366(16) 0.8717(4) 1.000 0.0313(8) . . C25 C Uani 0.24856(12) 0.70212(15) 0.8728(4) 1.000 0.0304(7) . . C26 C Uani 0.27757(11) 0.55791(15) 0.9356(4) 1.000 0.0336(7) . . O3 O Uani 0.42402(9) 0.00303(11) 0.1151(4) 1.000 0.0464(7) . . O4 O Uani 0.52088(8) 0.03707(11) 0.1718(4) 1.000 0.0444(7) . . O5 O Uani 0.34703(8) 0.11722(12) 0.0373(3) 1.000 0.0401(6) . . N7 N Uani 0.40873(12) 0.39017(14) 0.1437(5) 1.000 0.0445(8) . . C13 C Uani 0.44897(11) 0.14174(15) 0.1483(4) 1.000 0.0292(7) . . C14 C Uani 0.39125(11) 0.16990(16) 0.0929(4) 1.000 0.0302(7) . . C15 C Uani 0.37818(11) 0.25178(16) 0.0915(4) 1.000 0.0306(7) . . C16 C Uani 0.42213(11) 0.30873(15) 0.1447(4) 1.000 0.0312(7) . . C17 C Uani 0.47959(12) 0.28098(16) 0.2042(4) 1.000 0.0324(7) . . C18 C Uani 0.49244(11) 0.19940(16) 0.2048(4) 1.000 0.0293(7) . . C19 C Uani 0.46355(11) 0.05491(16) 0.1446(4) 1.000 0.0343(7) . . O1 O Uani 0.37623(9) 0.39892(12) 0.6673(4) 1.000 0.0456(7) . . N1 N Uani 0.45681(10) 0.11621(14) 0.6600(4) 1.000 0.0357(6) . . N2 N Uani 0.47736(10) 0.42040(13) 0.6508(5) 1.000 0.0429(8) . . N3 N Uani 0.47320(12) 0.50550(14) 0.6516(6) 1.000 0.0524(9) . . C1 C Uani 0.50073(12) 0.16579(17) 0.7201(4) 1.000 0.0360(8) . . C2 C Uani 0.49502(12) 0.24926(16) 0.7229(4) 1.000 0.0316(8) . . C3 C Uani 0.44037(10) 0.28289(15) 0.6621(4) 1.000 0.0291(7) . . C4 C Uani 0.39423(12) 0.23188(18) 0.6017(4) 1.000 0.0341(7) . . C5 C Uani 0.40420(12) 0.14910(18) 0.6020(4) 1.000 0.0365(8) . . C6 C Uani 0.42827(11) 0.37243(15) 0.6596(4) 1.000 0.0330(7) . . H5N H Uiso 0.2550(17) 0.0998(19) 0.952(6) 1.000 0.049(10) . . H6A H Uiso 0.1850(19) -0.022(2) 1.019(6) 1.000 0.049(10) . . H6B H Uiso 0.200(3) -0.027(4) 0.815(12) 1.000 0.13(2) . . H7 H Uiso 0.2773(13) 0.3545(18) 0.807(5) 1.000 0.033(8) . . H7O H Uiso 0.211(3) 0.466(4) 0.906(11) 1.000 0.13(2) . . H8 H Uiso 0.2657(16) 0.216(2) 0.794(6) 1.000 0.050(10) . . H8A H Uiso 0.3641(17) 0.907(2) 0.959(5) 1.000 0.044(10) . . H8B H Uiso 0.2983(16) 0.925(2) 0.918(5) 1.000 0.039(8) . . H8O H Uiso 0.372(3) 0.568(3) 0.987(11) 1.000 0.13(2) . . H10 H Uiso 0.0981(15) 0.254(2) 1.045(5) 1.000 0.042(9) . . H11 H Uiso 0.1190(13) 0.3984(17) 1.038(5) 1.000 0.028(7) . . H22 H Uiso 0.4025(15) 0.7736(19) 0.983(5) 1.000 0.041(9) . . H24 H Uiso 0.2289(17) 0.821(2) 0.856(6) 1.000 0.057(11) . . H25 H Uiso 0.2060(15) 0.677(2) 0.843(5) 1.000 0.048(10) . . H4O H Uiso 0.5315(19) -0.014(2) 0.158(8) 1.000 0.068(12) . . H5O H Uiso 0.3642(17) 0.063(2) 0.054(6) 1.000 0.059(11) . . H7A H Uiso 0.4402(17) 0.430(2) 0.153(7) 1.000 0.064(11) . . H7B H Uiso 0.373(2) 0.405(2) 0.076(7) 1.000 0.068(13) . . H15 H Uiso 0.3349(16) 0.2652(19) 0.059(5) 1.000 0.043(9) . . H17 H Uiso 0.5091(14) 0.3182(19) 0.237(5) 1.000 0.034(8) . . H18 H Uiso 0.5299(13) 0.1801(16) 0.251(4) 1.000 0.025(7) . . H1 H Uiso 0.5385(16) 0.132(2) 0.762(6) 1.000 0.054(10) . . H2 H Uiso 0.5245(16) 0.278(2) 0.757(6) 1.000 0.051(10) . . H2N H Uiso 0.513(2) 0.407(3) 0.629(8) 1.000 0.078(15) . . H3A H Uiso 0.444(2) 0.520(3) 0.556(7) 1.000 0.062(12) . . H3B H Uiso 0.451(2) 0.515(3) 0.757(8) 1.000 0.074(15) . . H4 H Uiso 0.3555(16) 0.252(2) 0.561(6) 1.000 0.048(10) . . H5 H Uiso 0.3732(16) 0.112(2) 0.564(6) 1.000 0.046(9) . . 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 O2 0.0270(9) 0.0363(10) 0.0754(15) 0.0045(11) -0.0034(11) -0.0090(7) O6 0.0354(10) 0.0323(9) 0.0682(15) -0.0001(10) -0.0064(11) 0.0075(8) O7 0.0331(10) 0.0285(9) 0.0724(15) 0.0024(10) -0.0081(11) -0.0019(7) O8 0.0231(9) 0.0458(11) 0.0618(14) 0.0055(10) -0.0032(9) 0.0050(8) N4 0.0318(11) 0.0284(10) 0.0433(12) 0.0028(10) -0.0052(10) -0.0031(8) N5 0.0292(11) 0.0249(10) 0.0562(15) -0.0008(11) -0.0050(11) -0.0031(8) N6 0.0445(14) 0.0243(10) 0.0655(19) 0.0005(13) -0.0007(14) -0.0037(9) N8 0.0383(14) 0.0335(12) 0.0550(15) -0.0020(12) -0.0030(13) -0.0102(10) C7 0.0264(12) 0.0319(12) 0.0428(14) 0.0045(12) 0.0014(11) -0.0041(10) C8 0.0267(12) 0.0322(14) 0.0348(15) 0.0005(11) -0.0002(10) -0.0017(10) C9 0.0259(11) 0.0265(11) 0.0317(12) -0.0006(10) -0.0043(10) -0.0031(8) C10 0.0220(10) 0.0342(12) 0.0365(13) -0.0022(11) -0.0021(10) -0.0025(9) C11 0.0269(12) 0.0321(12) 0.0420(14) -0.0007(11) -0.0042(11) 0.0015(10) C12 0.0294(12) 0.0283(11) 0.0372(13) -0.0002(11) -0.0035(11) -0.0034(9) C20 0.0221(10) 0.0316(12) 0.0350(12) -0.0012(11) 0.0010(10) -0.0003(9) C21 0.0231(11) 0.0381(13) 0.0327(13) 0.0024(11) 0.0014(10) 0.0038(9) C22 0.0244(11) 0.0415(15) 0.0371(14) 0.0009(12) -0.0009(11) -0.0080(10) C23 0.0309(12) 0.0357(12) 0.0313(12) -0.0005(11) -0.0003(11) -0.0077(10) C24 0.0290(12) 0.0287(13) 0.0363(15) -0.0012(11) -0.0006(11) -0.0017(10) C25 0.0261(12) 0.0301(12) 0.0350(14) -0.0021(10) -0.0017(10) -0.0010(9) C26 0.0301(12) 0.0310(12) 0.0398(14) -0.0040(12) 0.0005(11) 0.0027(9) O3 0.0312(9) 0.0306(9) 0.0774(17) -0.0046(10) -0.0046(10) -0.0043(7) O4 0.0282(9) 0.0284(9) 0.0765(16) -0.0006(11) -0.0045(11) 0.0011(7) O5 0.0242(8) 0.0376(10) 0.0584(13) -0.0021(10) -0.0065(9) -0.0057(7) N7 0.0397(13) 0.0288(11) 0.0650(18) 0.0003(12) -0.0064(14) 0.0016(10) C13 0.0256(11) 0.0284(11) 0.0336(12) -0.0007(11) 0.0007(10) -0.0029(9) C14 0.0231(11) 0.0348(12) 0.0326(12) -0.0019(11) 0.0016(10) -0.0058(9) C15 0.0218(10) 0.0359(13) 0.0342(13) 0.0027(11) -0.0008(10) -0.0005(9) C16 0.0315(12) 0.0296(11) 0.0326(13) 0.0002(11) 0.0023(11) -0.0006(9) C17 0.0276(11) 0.0324(13) 0.0371(14) -0.0037(12) -0.0004(11) -0.0066(10) C18 0.0225(11) 0.0335(12) 0.0320(13) -0.0010(11) -0.0013(10) -0.0023(9) C19 0.0281(12) 0.0313(12) 0.0434(14) -0.0015(12) 0.0006(12) -0.0028(9) O1 0.0279(9) 0.0390(10) 0.0699(15) 0.0064(11) 0.0069(11) 0.0053(7) N1 0.0309(10) 0.0325(10) 0.0437(13) 0.0010(11) -0.0002(10) -0.0007(8) N2 0.0269(10) 0.0284(10) 0.0735(19) 0.0013(13) 0.0061(13) 0.0011(8) N3 0.0368(12) 0.0284(11) 0.092(2) 0.0051(15) 0.0053(17) -0.0020(9) C1 0.0293(12) 0.0381(14) 0.0405(15) 0.0030(12) -0.0024(11) 0.0005(10) C2 0.0261(11) 0.0329(13) 0.0359(15) 0.0010(11) -0.0024(10) -0.0021(10) C3 0.0231(11) 0.0346(12) 0.0295(12) 0.0006(11) 0.0039(10) 0.0001(9) C4 0.0240(11) 0.0412(14) 0.0372(13) 0.0013(12) -0.0001(10) 0.0018(10) C5 0.0288(12) 0.0366(13) 0.0441(15) -0.0032(12) -0.0012(11) -0.0038(10) C6 0.0274(11) 0.0323(12) 0.0393(14) 0.0025(12) 0.0053(11) 0.0030(9) #=============================================================================== _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; 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 O2 C12 1.227(3) . . yes O6 C26 1.253(3) . . yes O7 C26 1.296(3) . . yes O8 C21 1.367(3) . . yes O7 H7O 1.21(7) . . no O8 H8O 1.01(5) . . no O3 C19 1.237(3) . . yes O4 C19 1.304(3) . . yes O5 C14 1.363(3) . . yes O4 H4O 0.88(3) . . no O5 H5O 0.98(3) . . no O1 C6 1.222(3) . . yes N4 C7 1.336(4) . . yes N4 C11 1.338(3) . . yes N5 N6 1.426(3) . . yes N5 C12 1.329(3) . . yes N8 C23 1.364(3) . . yes N4 H7O 1.35(7) . . no N5 H5N 0.93(4) . . no N6 H6A 0.90(4) . . no N6 H6B 0.94(8) . . no N8 H8A 0.79(4) . . no N8 H8B 0.92(3) . . no N7 C16 1.377(3) . . yes N7 H7B 0.96(4) . . no N7 H7A 0.96(4) . . no N1 C5 1.342(4) . . yes N1 C1 1.337(4) . . yes N2 C6 1.337(3) . . yes N2 N3 1.408(3) . . yes N2 H2N 0.83(4) . . no N3 H3A 0.98(5) . . no N3 H3B 0.92(5) . . no C7 C8 1.393(4) . . no C8 C9 1.383(4) . . no C9 C10 1.382(4) . . no C9 C12 1.514(3) . . no C10 C11 1.394(4) . . no C20 C25 1.397(4) . . no C20 C26 1.471(3) . . no C20 C21 1.410(3) . . no C21 C22 1.390(4) . . no C22 C23 1.397(4) . . no C23 C24 1.416(4) . . no C24 C25 1.374(4) . . no C7 H7 0.87(3) . . no C8 H8 0.96(4) . . no C10 H10 1.02(3) . . no C11 H11 1.06(3) . . no C22 H22 0.90(3) . . no C24 H24 0.94(4) . . no C25 H25 1.04(3) . . no C13 C14 1.406(4) . . no C13 C19 1.469(4) . . no C13 C18 1.408(4) . . no C14 C15 1.382(4) . . no C15 C16 1.400(4) . . no C16 C17 1.407(4) . . no C17 C18 1.376(4) . . no C15 H15 1.00(3) . . no C17 H17 0.92(3) . . no C18 H18 0.94(3) . . no C1 C2 1.384(4) . . no C2 C3 1.391(4) . . no C3 C4 1.387(4) . . no C3 C6 1.502(4) . . no C4 C5 1.384(4) . . no C1 H1 1.04(4) . . no C2 H2 0.84(4) . . no C4 H4 0.96(4) . . no C5 H5 0.96(3) . . 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 C26 O7 H7O 115(3) . . . no C21 O8 H8O 96(4) . . . no C19 O4 H4O 117(3) . . . no C14 O5 H5O 106(2) . . . no C7 N4 C11 119.2(2) . . . yes N6 N5 C12 122.1(2) . . . yes C11 N4 H7O 120(3) . . . no C7 N4 H7O 121(3) . . . no C12 N5 H5N 124(2) . . . no N6 N5 H5N 114(2) . . . no H6A N6 H6B 113(5) . . . no N5 N6 H6B 115(4) . . . no N5 N6 H6A 111(2) . . . no H8A N8 H8B 123(3) . . . no C23 N8 H8B 115(2) . . . no C23 N8 H8A 118(2) . . . no C16 N7 H7A 121(2) . . . no H7A N7 H7B 117(3) . . . no C16 N7 H7B 115(2) . . . no C1 N1 C5 118.2(2) . . . yes N3 N2 C6 122.6(2) . . . yes C6 N2 H2N 128(3) . . . no N3 N2 H2N 109(3) . . . no N2 N3 H3B 102(3) . . . no N2 N3 H3A 107(3) . . . no H3A N3 H3B 102(4) . . . no N4 C7 C8 122.3(2) . . . yes C7 C8 C9 118.6(2) . . . no C8 C9 C12 122.6(2) . . . no C10 C9 C12 118.3(2) . . . no C8 C9 C10 119.2(2) . . . no C9 C10 C11 119.1(2) . . . no N4 C11 C10 121.7(2) . . . yes O2 C12 N5 124.2(2) . . . yes O2 C12 C9 120.3(2) . . . yes N5 C12 C9 115.5(2) . . . yes C25 C20 C26 121.9(2) . . . no C21 C20 C26 120.2(2) . . . no C21 C20 C25 117.8(2) . . . no O8 C21 C22 119.0(2) . . . yes O8 C21 C20 120.7(2) . . . yes C20 C21 C22 120.3(2) . . . no C21 C22 C23 121.2(2) . . . no N8 C23 C22 121.8(2) . . . yes C22 C23 C24 118.3(2) . . . no N8 C23 C24 119.8(2) . . . yes C23 C24 C25 119.9(2) . . . no C20 C25 C24 122.3(2) . . . no O6 C26 C20 121.2(2) . . . yes O7 C26 C20 116.2(2) . . . yes O6 C26 O7 122.6(2) . . . yes C8 C7 H7 120(2) . . . no N4 C7 H7 117(2) . . . no C7 C8 H8 119(2) . . . no C9 C8 H8 122(2) . . . no C11 C10 H10 117.7(19) . . . no C9 C10 H10 122.9(19) . . . no C10 C11 H11 122.1(16) . . . no N4 C11 H11 115.9(16) . . . no C21 C22 H22 123(2) . . . no C23 C22 H22 116(2) . . . no C23 C24 H24 120(2) . . . no C25 C24 H24 120(2) . . . no C20 C25 H25 113.2(19) . . . no C24 C25 H25 124.4(19) . . . no C14 C13 C18 117.9(2) . . . no C14 C13 C19 120.9(2) . . . no C18 C13 C19 121.2(2) . . . no O5 C14 C13 120.8(2) . . . yes C13 C14 C15 120.8(2) . . . no O5 C14 C15 118.4(2) . . . yes C14 C15 C16 120.9(2) . . . no C15 C16 C17 118.7(2) . . . no N7 C16 C15 120.6(2) . . . yes N7 C16 C17 120.7(2) . . . yes C16 C17 C18 120.2(2) . . . no C13 C18 C17 121.5(2) . . . no O3 C19 O4 122.9(2) . . . yes O4 C19 C13 115.3(2) . . . yes O3 C19 C13 121.8(2) . . . yes C16 C15 H15 124.5(18) . . . no C14 C15 H15 114.5(18) . . . no C16 C17 H17 119.2(19) . . . no C18 C17 H17 120.5(19) . . . no C13 C18 H18 117.7(16) . . . no C17 C18 H18 120.7(17) . . . no N1 C1 C2 123.4(2) . . . yes C1 C2 C3 118.1(2) . . . no C2 C3 C4 119.0(2) . . . no C4 C3 C6 117.8(2) . . . no C2 C3 C6 123.3(2) . . . no C3 C4 C5 119.0(2) . . . no N1 C5 C4 122.4(3) . . . yes O1 C6 C3 121.1(2) . . . yes N2 C6 C3 116.2(2) . . . yes O1 C6 N2 122.7(2) . . . yes N1 C1 H1 109.8(19) . . . no C2 C1 H1 126.9(19) . . . no C1 C2 H2 120(2) . . . no C3 C2 H2 122(2) . . . no C3 C4 H4 122(2) . . . no C5 C4 H4 119(2) . . . no N1 C5 H5 116(2) . . . no C4 C5 H5 121(2) . . . 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 N4 C7 C8 -1.1(4) . . . . no C7 N4 C11 C10 0.7(4) . . . . no N6 N5 C12 O2 2.1(5) . . . . no N6 N5 C12 C9 -177.6(3) . . . . no C1 N1 C5 C4 0.3(4) . . . . no C5 N1 C1 C2 -1.0(5) . . . . no N3 N2 C6 C3 -178.5(3) . . . . no N3 N2 C6 O1 0.7(6) . . . . no N4 C7 C8 C9 0.4(4) . . . . no C7 C8 C9 C12 178.6(3) . . . . no C7 C8 C9 C10 0.8(4) . . . . no C10 C9 C12 N5 -154.4(3) . . . . no C12 C9 C10 C11 -179.0(3) . . . . no C8 C9 C12 O2 -151.8(3) . . . . no C8 C9 C10 C11 -1.2(4) . . . . no C10 C9 C12 O2 25.9(4) . . . . no C8 C9 C12 N5 27.9(4) . . . . no C9 C10 C11 N4 0.5(4) . . . . no C26 C20 C21 O8 5.9(4) . . . . no C26 C20 C25 C24 174.0(3) . . . . no C21 C20 C26 O6 0.5(4) . . . . no C21 C20 C25 C24 -3.0(4) . . . . no C25 C20 C26 O6 -176.4(3) . . . . no C25 C20 C26 O7 2.5(4) . . . . no C25 C20 C21 C22 3.5(4) . . . . no C21 C20 C26 O7 179.4(3) . . . . no C26 C20 C21 C22 -173.6(3) . . . . no C25 C20 C21 O8 -177.0(3) . . . . no O8 C21 C22 C23 179.9(3) . . . . no C20 C21 C22 C23 -0.6(4) . . . . no C21 C22 C23 C24 -2.7(4) . . . . no C21 C22 C23 N8 179.5(3) . . . . no C22 C23 C24 C25 3.2(4) . . . . no N8 C23 C24 C25 -179.0(3) . . . . no C23 C24 C25 C20 -0.3(4) . . . . no C18 C13 C14 C15 1.0(4) . . . . no C19 C13 C18 C17 178.3(3) . . . . no C19 C13 C14 C15 -178.2(3) . . . . no C14 C13 C18 C17 -0.8(4) . . . . no C18 C13 C19 O3 171.8(3) . . . . no C18 C13 C19 O4 -9.2(4) . . . . no C19 C13 C14 O5 1.1(4) . . . . no C14 C13 C19 O4 170.0(3) . . . . no C18 C13 C14 O5 -179.8(3) . . . . no C14 C13 C19 O3 -9.1(5) . . . . no C13 C14 C15 C16 0.2(4) . . . . no O5 C14 C15 C16 -179.1(3) . . . . no C14 C15 C16 N7 -179.7(3) . . . . no C14 C15 C16 C17 -1.6(4) . . . . no C15 C16 C17 C18 1.7(4) . . . . no N7 C16 C17 C18 179.9(3) . . . . no C16 C17 C18 C13 -0.6(4) . . . . no N1 C1 C2 C3 0.9(4) . . . . no C1 C2 C3 C4 0.0(4) . . . . no C1 C2 C3 C6 179.5(3) . . . . no C2 C3 C6 N2 24.6(4) . . . . no C4 C3 C6 O1 24.9(4) . . . . no C4 C3 C6 N2 -155.9(3) . . . . no C2 C3 C6 O1 -154.6(3) . . . . no C2 C3 C4 C5 -0.7(4) . . . . no C6 C3 C4 C5 179.8(3) . . . . no C3 C4 C5 N1 0.5(4) . . . . 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 O1 C7 3.364(4) . . no O1 O6 3.198(4) . . no O1 N3 2.760(3) . . no O1 N6 3.016(4) . 3_554 no O2 N3 3.055(4) . 3_545 no O2 N6 2.783(4) . . no O2 O8 3.125(4) . 3_544 no O3 C1 3.328(4) . 2_654 no O3 O5 2.592(3) . . no O3 N8 3.066(4) . 1_544 no O4 N1 2.580(3) . 2_654 no O4 C1 3.402(4) . 2_654 no O5 O3 2.592(3) . . no O5 N5 3.041(3) . 1_554 no O6 O8 2.552(3) . . no O6 O1 3.198(4) . . no O6 N7 3.020(4) . 1_556 no O8 O2 3.125(4) . 3_555 no O8 N2 3.029(3) . 2_665 no O8 O6 2.552(3) . . no O1 H4 2.59(3) . . no O1 H7 2.50(3) . . no O1 H3A 2.62(5) . . no O1 H6A 2.16(4) . 3_554 no O1 H3B 2.60(5) . . no O2 H10 2.64(3) . . no O2 H3A 2.16(5) . 3_545 no O2 H6A 2.73(4) . . no O3 H5O 1.70(4) . . no O3 H1 2.61(4) . 2_654 no O3 H8A 2.35(3) . 1_544 no O4 H18 2.44(3) . . no O4 H11 2.59(3) . 4_554 no O5 H5N 2.13(4) . 1_554 no O5 H25 2.70(4) . 3_544 no O6 H6B 2.50(9) . 3_555 no O6 H7B 2.19(4) . 1_556 no O6 H8O 1.57(6) . . no O7 H25 2.36(3) . . no O7 H5 2.68(4) . 3_555 no O8 H2N 2.23(5) . 2_665 no O8 H3B 2.66(5) . . no N1 O4 2.580(3) . 2_655 no N1 C19 3.323(4) . 2_655 no N2 O8 3.029(3) . 2_664 no N3 N7 3.107(4) . 2_665 no N3 O1 2.760(3) . . no N3 O2 3.055(4) . 3_554 no N5 O5 3.041(3) . 1_556 no N6 O1 3.016(4) . 3_545 no N6 N8 3.173(4) . 1_545 no N6 O2 2.783(4) . . no N7 O6 3.020(4) . 1_554 no N7 N3 3.107(4) . 2_664 no N8 N6 3.173(4) . 1_565 no N8 C11 3.312(4) . 3_554 no N8 O3 3.066(4) . 1_566 no N1 H4O 1.71(3) . 2_655 no N2 H2 2.68(3) . . no N3 H7A 2.18(4) . 2_665 no N5 H8 2.67(4) . . no N6 H8B 2.26(3) . 1_545 no C1 O4 3.402(4) . 2_655 no C1 O3 3.328(4) . 2_655 no C1 C13 3.342(4) . 1_556 no C1 C18 3.578(4) . 1_556 no C2 C17 3.560(4) . 1_556 no C2 C16 3.598(4) . 1_556 no C3 C16 3.563(4) . 1_556 no C3 C17 3.444(4) . . no C3 C15 3.449(4) . 1_556 no C4 C15 3.600(4) . 1_556 no C4 C17 3.540(4) . . no C4 C25 3.577(4) . 3_544 no C5 C13 3.449(4) . . no C5 C18 3.576(4) . . no C7 C24 3.550(4) . 3_544 no C7 O1 3.364(4) . . no C7 C23 3.429(4) . 3_544 no C8 C25 3.566(4) . 3_544 no C8 C24 3.509(4) . 3_544 no C8 C23 3.502(4) . 3_544 no C9 C21 3.549(4) . 3_544 no C9 C22 3.571(4) . 3_544 no C10 C18 3.587(4) . 4_456 no C10 C23 3.374(4) . 3_545 no C10 C22 3.458(4) . 3_545 no C11 C23 3.368(4) . 3_545 no C11 N8 3.312(4) . 3_545 no C12 C21 3.507(4) . 3_544 no C13 C5 3.449(4) . . no C13 C1 3.342(4) . 1_554 no C15 C4 3.600(4) . 1_554 no C15 C3 3.449(4) . 1_554 no C15 C25 3.545(4) . 3_544 no C16 C3 3.563(4) . 1_554 no C16 C2 3.598(4) . 1_554 no C17 C3 3.444(4) . . no C17 C2 3.560(4) . 1_554 no C17 C4 3.540(4) . . no C18 C1 3.578(4) . 1_554 no C18 C5 3.576(4) . . no C18 C10 3.587(4) . 4_554 no C19 N1 3.323(4) . 2_654 no C21 C12 3.507(4) . 3_555 no C21 C9 3.549(4) . 3_555 no C22 C9 3.571(4) . 3_555 no C22 C10 3.458(4) . 3_554 no C23 C10 3.374(4) . 3_554 no C23 C8 3.502(4) . 3_555 no C23 C11 3.368(4) . 3_554 no C23 C7 3.429(4) . 3_555 no C24 C7 3.550(4) . 3_555 no C24 C8 3.509(4) . 3_555 no C25 C8 3.566(4) . 3_555 no C25 C4 3.577(4) . 3_555 no C25 C15 3.545(4) . 3_555 no C1 H22 2.91(3) . 2_664 no C1 H4O 2.64(3) . 2_655 no C2 H2N 2.72(5) . . no C2 H22 2.87(3) . 2_664 no C4 H25 3.03(3) . 3_544 no C5 H25 3.10(3) . 3_544 no C5 H4O 2.67(4) . 2_655 no C7 H15 2.78(4) . 1_556 no C8 H15 2.69(4) . 1_556 no C8 H5N 2.64(3) . . no C10 H2 3.07(4) . 4_455 no C11 H1 2.88(4) . 4_455 no C14 H25 2.80(3) . 3_544 no C15 H25 2.88(3) . 3_544 no C17 H10 2.90(3) . 4_554 no C18 H10 2.70(3) . 4_554 no C18 H22 3.10(3) . 2_664 no C19 H5O 2.28(4) . . no C22 H10 3.09(4) . 3_554 no C22 H18 2.94(3) . 2_665 no C24 H4 2.95(4) . 3_555 no C25 H4 2.78(4) . 3_555 no C25 H8 3.09(4) . 3_555 no C26 H8O 2.11(7) . . no H1 O3 2.61(4) . 2_655 no H1 C11 2.88(4) . 4_555 no H1 H4O 2.59(5) . 2_655 no H2 H2N 2.34(6) . . no H2 N2 2.68(3) . . no H2 C10 3.07(4) . 4_555 no H2N H2 2.34(6) . . no H2N O8 2.23(5) . 2_664 no H2N C2 2.72(5) . . no H3A O1 2.62(5) . . no H3A O2 2.16(5) . 3_554 no H3B O1 2.60(5) . . no H3B O8 2.66(5) . . no H3B H8O 2.56(9) . . no H4 C24 2.95(4) . 3_544 no H4 C25 2.78(4) . 3_544 no H4 H25 2.42(5) . 3_544 no H4 O1 2.59(3) . . no H4O N1 1.71(3) . 2_654 no H4O C1 2.64(3) . 2_654 no H4O C5 2.67(4) . 2_654 no H4O H1 2.59(5) . 2_654 no H5 O7 2.68(4) . 3_544 no H5 H25 2.60(5) . 3_544 no H5N H8 2.25(5) . . no H5N C8 2.64(3) . . no H5N H5O 2.58(5) . 1_556 no H5N O5 2.13(4) . 1_556 no H5O H5N 2.58(5) . 1_554 no H5O C19 2.28(4) . . no H5O O3 1.70(4) . . no H6A O1 2.16(4) . 3_545 no H6A O2 2.73(4) . . no H6B H8B 2.41(8) . 1_545 no H6B O6 2.50(9) . 3_544 no H7 O1 2.50(3) . . no H7A H17 2.46(5) . . no H7A N3 2.18(4) . 2_664 no H7B O6 2.19(4) . 1_554 no H7B H15 2.46(5) . . no H8 H5N 2.25(5) . . no H8 C25 3.09(4) . 3_544 no H8 N5 2.67(4) . . no H8 H15 2.59(5) . 1_556 no H8A H22 2.37(5) . . no H8A O3 2.35(3) . 1_566 no H8B H6B 2.41(8) . 1_565 no H8B H24 2.34(5) . . no H8B N6 2.26(3) . 1_565 no H8O O6 1.57(6) . . no H8O H3B 2.56(9) . . no H8O C26 2.11(7) . . no H10 C18 2.70(3) . 4_456 no H10 H18 2.38(4) . 4_456 no H10 C17 2.90(3) . 4_456 no H10 O2 2.64(3) . . no H10 C22 3.09(4) . 3_545 no H11 O4 2.59(3) . 4_456 no H15 C8 2.69(4) . 1_554 no H15 C7 2.78(4) . 1_554 no H15 H7B 2.46(5) . . no H15 H8 2.59(5) . 1_554 no H17 H7A 2.46(5) . . no H18 H10 2.38(4) . 4_554 no H18 O4 2.44(3) . . no H18 H22 2.37(4) . 2_664 no H18 C22 2.94(3) . 2_664 no H22 C18 3.10(3) . 2_665 no H22 H18 2.37(4) . 2_665 no H22 C1 2.91(3) . 2_665 no H22 C2 2.87(3) . 2_665 no H22 H8A 2.37(5) . . no H24 H8B 2.34(5) . . no H25 O7 2.36(3) . . no H25 H5 2.60(5) . 3_555 no H25 O5 2.70(4) . 3_555 no H25 C4 3.03(3) . 3_555 no H25 C5 3.10(3) . 3_555 no H25 C14 2.80(3) . 3_555 no H25 C15 2.88(3) . 3_555 no H25 H4 2.42(5) . 3_555 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # N2 H2N O8 0.83(4) 2.23(5) 3.029(3) 164(5) 2_664 yes N3 H3A O2 0.98(5) 2.16(5) 3.055(4) 152(4) 3_554 yes O4 H4O N1 0.88(3) 1.71(3) 2.580(3) 170(4) 2_654 yes N5 H5N O5 0.93(4) 2.13(4) 3.041(3) 167(3) 1_556 yes O5 H5O O3 0.98(3) 1.70(4) 2.592(3) 149(3) . yes N6 H6A O1 0.90(4) 2.16(4) 3.016(4) 159(3) 3_545 yes N6 H6B O6 0.94(8) 2.50(9) 3.297(5) 143(6) 3_544 yes N7 H7A N3 0.96(4) 2.18(4) 3.107(4) 165(3) 2_664 yes N7 H7B O6 0.96(4) 2.19(4) 3.020(4) 144(3) 1_554 yes O7 H7O N4 1.21(7) 1.35(7) 2.564(3) 178(9) . yes N8 H8A O3 0.79(4) 2.35(3) 3.066(4) 151(3) 1_566 yes N8 H8B N6 0.92(3) 2.26(3) 3.173(4) 174(3) 1_565 yes O8 H8O O6 1.01(5) 1.57(6) 2.552(3) 165(6) . yes C7 H7 O1 0.87(3) 2.50(3) 3.364(4) 173(3) . yes C11 H11 O4 1.06(3) 2.59(3) 3.604(4) 161(2) 4_456 yes C25 H25 O7 1.04(3) 2.36(3) 2.781(3) 103(2) . yes #===END # Attachment 'web_deposit_cif_file_6_PawelGrobelny_1289286463.cif' # CIF-file generated for datam in Pna2(1) #=============================================================================== data_datam7 _database_code_depnum_ccdc_archive 'CCDC 800236' #TrackingRef 'web_deposit_cif_file_6_PawelGrobelny_1289286463.cif' #=============================================================================== _chemical_name_systematic ; ; _chemical_name_common 'Isoniazid:4-aminosalicylic acid co-crystal' _chemical_melting_point ? _chemical_formula_moiety 'C7 H7 N O3, C6 H7 N3 O' _chemical_formula_structural ? _chemical_formula_sum 'C13 H14 N4 O4' _chemical_formula_iupac ? _chemical_formula_weight 290.28 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_space_group_name_H-M 'P n a 21' _symmetry_Int_Tables_number 33 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,1/2+z 3 1/2-x,1/2+y,1/2+z 4 1/2+x,1/2-y,z _cell_length_a 21.893(2) _cell_length_b 16.5073(18) _cell_length_c 7.2990(7) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2637.8(5) _cell_formula_units_Z 8 _cell_measurement_temperature 220(2) _cell_measurement_reflns_used 6579 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 27.5 _cell_special_details ; ; _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.462 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 0.111 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.832 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' #=============================================================================== _exptl_special_details ; ; _diffrn_ambient_temperature 220(2) _diffrn_source_power 0.6 _diffrn_source_voltage 50.0 _diffrn_source_current 12.0 _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_source 'Sealed Tube' _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_measurement_specimen_support Fiber _diffrn_detector CCD _diffrn_measurement_device ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_detector_area_resol_mean 13.6612 _diffrn_measurement_method 'profile data from \w-scans' _diffrn_reflns_number 27057 _diffrn_reflns_av_R_equivalents 0.0527 _diffrn_reflns_av_sigmaI/netI 0.0281 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 27.51 _reflns_number_total 3269 _reflns_number_gt 3017 _reflns_threshold_expression >2\s(I) _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measurement_details ; scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 0.0000 XTD: 49.4115 2theta: 29.5807 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 120.0000 XTD: 49.4115 2theta: 29.5807 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 240.0000 XTD: 49.4115 2theta: 29.5807 ; _diffrn_orient_matrix_UB_11 0.016907 _diffrn_orient_matrix_UB_12 -0.134949 _diffrn_orient_matrix_UB_13 0.016536 _diffrn_orient_matrix_UB_21 0.060045 _diffrn_orient_matrix_UB_22 0.007770 _diffrn_orient_matrix_UB_23 0.002020 _diffrn_orient_matrix_UB_31 -0.002207 _diffrn_orient_matrix_UB_32 0.005277 _diffrn_orient_matrix_UB_33 0.045318 _diffrn_orient_matrix_type d*Trek _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement ? _computing_molecular_graphics ? _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== _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^ > 2\s(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^)+(0.0727P)^2^+0.2199P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3269 _refine_ls_number_parameters 492 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0469 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_ref 0.1238 _refine_ls_wR_factor_gt 0.1118 _refine_ls_goodness_of_fit_ref 1.161 _refine_ls_restrained_S_all 1.161 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.197 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.057 #=============================================================================== loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags O3 O Uani 0.42384(9) 0.00361(11) 0.1155(4) 1.000 0.0511(8) . . O4 O Uani 0.52069(8) 0.03753(11) 0.1719(4) 1.000 0.0484(7) . . O5 O Uani 0.34693(8) 0.11760(12) 0.0378(3) 1.000 0.0435(6) . . N7 N Uani 0.40881(12) 0.39032(15) 0.1433(5) 1.000 0.0474(9) . . C13 C Uani 0.44889(11) 0.14213(15) 0.1489(4) 1.000 0.0314(7) . . C14 C Uani 0.39115(11) 0.17043(16) 0.0933(4) 1.000 0.0324(7) . . C15 C Uani 0.37824(11) 0.25232(16) 0.0915(4) 1.000 0.0330(7) . . C16 C Uani 0.42197(11) 0.30913(15) 0.1438(4) 1.000 0.0337(7) . . C17 C Uani 0.47957(12) 0.28160(16) 0.2036(4) 1.000 0.0351(8) . . C18 C Uani 0.49213(11) 0.19962(16) 0.2042(4) 1.000 0.0322(7) . . C19 C Uani 0.46328(11) 0.05556(16) 0.1449(4) 1.000 0.0374(8) . . O6 O Uani 0.18303(9) 0.00744(12) 0.4834(4) 1.000 0.0492(7) . . O7 O Uani 0.27833(8) 0.03821(11) 0.4008(4) 1.000 0.0477(7) . . O8 O Uani 0.10159(9) 0.11850(14) 0.4905(4) 1.000 0.0468(7) . . N8 N Uani 0.16794(12) 0.39298(14) 0.4198(4) 1.000 0.0462(8) . . C20 C Uani 0.20717(10) 0.14479(14) 0.4183(4) 1.000 0.0311(7) . . C21 C Uani 0.14754(11) 0.17186(17) 0.4538(4) 1.000 0.0349(7) . . C22 C Uani 0.13462(12) 0.25430(18) 0.4545(4) 1.000 0.0373(8) . . C23 C Uani 0.17988(11) 0.31159(15) 0.4177(4) 1.000 0.0353(7) . . C24 C Uani 0.23894(12) 0.28380(16) 0.3720(4) 1.000 0.0342(8) . . C25 C Uani 0.25140(12) 0.20261(16) 0.3729(4) 1.000 0.0334(8) . . C26 C Uani 0.22230(12) 0.05809(15) 0.4352(4) 1.000 0.0361(8) . . O1 O Uani 0.37639(9) 0.39857(13) 0.6664(4) 1.000 0.0501(7) . . N1 N Uani 0.45693(10) 0.11605(14) 0.6606(4) 1.000 0.0389(7) . . N2 N Uani 0.47730(10) 0.41988(14) 0.6508(5) 1.000 0.0473(8) . . N3 N Uani 0.47291(13) 0.50532(15) 0.6505(7) 1.000 0.0573(12) . . C1 C Uani 0.50081(12) 0.16532(17) 0.7193(4) 1.000 0.0391(8) . . C2 C Uani 0.49490(11) 0.24880(16) 0.7227(4) 1.000 0.0349(8) . . C3 C Uani 0.44039(10) 0.28272(15) 0.6622(4) 1.000 0.0315(7) . . C4 C Uani 0.39431(12) 0.23131(19) 0.6020(4) 1.000 0.0377(8) . . C5 C Uani 0.40432(12) 0.14864(18) 0.6021(5) 1.000 0.0391(8) . . C6 C Uani 0.42831(11) 0.37196(15) 0.6592(4) 1.000 0.0354(7) . . O2 O Uani 0.11407(9) 0.10625(12) 0.9168(4) 1.000 0.0504(7) . . N4 N Uani 0.20128(10) 0.38553(12) 0.9098(4) 1.000 0.0369(7) . . N5 N Uani 0.21527(11) 0.08168(13) 0.9313(4) 1.000 0.0393(7) . . N6 N Uani 0.20979(13) -0.00421(14) 0.9297(5) 1.000 0.0484(9) . . C7 C Uani 0.24304(12) 0.33406(16) 0.8456(4) 1.000 0.0365(8) . . C8 C Uani 0.23486(12) 0.25056(16) 0.8475(4) 1.000 0.0331(8) . . C9 C Uani 0.18092(11) 0.21996(13) 0.9179(4) 1.000 0.0301(7) . . C10 C Uani 0.13720(11) 0.27303(17) 0.9814(4) 1.000 0.0335(7) . . C11 C Uani 0.14860(11) 0.35570(16) 0.9759(4) 1.000 0.0368(8) . . C12 C Uani 0.16702(11) 0.13010(15) 0.9229(4) 1.000 0.0347(7) . . H4O H Uiso 0.531(2) -0.022(3) 0.161(8) 1.000 0.081(14) . . H5O H Uiso 0.3652(16) 0.067(2) 0.056(6) 1.000 0.056(10) . . H7A H Uiso 0.4394(18) 0.425(2) 0.148(7) 1.000 0.065(11) . . H7B H Uiso 0.373(2) 0.409(2) 0.076(7) 1.000 0.073(13) . . H15 H Uiso 0.3365(13) 0.2686(17) 0.053(5) 1.000 0.034(7) . . H17 H Uiso 0.5101(12) 0.3195(16) 0.236(4) 1.000 0.027(7) . . H18 H Uiso 0.5305(12) 0.1753(16) 0.253(4) 1.000 0.026(7) . . H7O H Uiso 0.287(3) -0.022(4) 0.402(11) 1.000 0.13(2) . . H8A H Uiso 0.1337(18) 0.408(2) 0.461(6) 1.000 0.056(11) . . H8B H Uiso 0.2035(17) 0.433(2) 0.408(6) 1.000 0.056(10) . . H8O H Uiso 0.127(3) 0.070(4) 0.475(12) 1.000 0.15(3) . . H22 H Uiso 0.0985(15) 0.2732(19) 0.480(5) 1.000 0.042(9) . . H24 H Uiso 0.2700(16) 0.318(2) 0.356(6) 1.000 0.058(11) . . H25 H Uiso 0.2922(15) 0.1829(19) 0.349(5) 1.000 0.049(10) . . H1 H Uiso 0.5374(15) 0.130(2) 0.759(5) 1.000 0.049(9) . . H2 H Uiso 0.5265(16) 0.279(2) 0.765(5) 1.000 0.051(10) . . H2N H Uiso 0.5118(19) 0.402(2) 0.637(8) 1.000 0.075(14) . . H3A H Uiso 0.450(2) 0.518(3) 0.752(8) 1.000 0.084(16) . . H3B H Uiso 0.447(2) 0.520(3) 0.546(7) 1.000 0.077(14) . . H4 H Uiso 0.3549(16) 0.256(2) 0.565(5) 1.000 0.052(10) . . H5 H Uiso 0.3743(14) 0.1113(19) 0.564(5) 1.000 0.039(8) . . H5N H Uiso 0.2546(18) 0.097(2) 0.951(6) 1.000 0.061(11) . . H6A H Uiso 0.183(2) -0.023(3) 1.020(6) 1.000 0.057(11) . . H6B H Uiso 0.197(3) -0.020(4) 0.818(10) 1.000 0.101(19) . . H7 H Uiso 0.2772(12) 0.3524(16) 0.808(4) 1.000 0.026(7) . . H8 H Uiso 0.2636(15) 0.215(2) 0.804(6) 1.000 0.048(10) . . H10 H Uiso 0.0991(14) 0.253(2) 1.045(5) 1.000 0.044(9) . . H11 H Uiso 0.1187(14) 0.4005(17) 1.023(5) 1.000 0.032(7) . . 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 O3 0.0350(10) 0.0337(10) 0.0846(18) -0.0061(11) -0.0034(11) -0.0058(7) O4 0.0295(9) 0.0323(9) 0.0833(16) 0.0013(11) -0.0042(11) 0.0005(7) O5 0.0271(9) 0.0392(10) 0.0643(13) -0.0020(10) -0.0069(9) -0.0058(7) N7 0.0428(14) 0.0313(11) 0.0682(19) 0.0007(12) -0.0068(14) 0.0017(10) C13 0.0283(11) 0.0294(11) 0.0365(12) -0.0015(11) 0.0020(10) -0.0024(9) C14 0.0252(11) 0.0369(13) 0.0350(12) -0.0009(11) 0.0011(10) -0.0054(9) C15 0.0229(10) 0.0376(14) 0.0385(14) 0.0030(11) -0.0012(10) -0.0006(9) C16 0.0336(12) 0.0334(12) 0.0341(13) -0.0017(11) 0.0021(11) -0.0013(9) C17 0.0301(12) 0.0353(13) 0.0400(14) -0.0039(12) -0.0010(11) -0.0055(10) C18 0.0255(11) 0.0354(12) 0.0356(14) -0.0017(11) -0.0015(10) -0.0015(9) C19 0.0315(12) 0.0347(13) 0.0459(14) 0.0013(12) -0.0005(12) -0.0036(10) O6 0.0379(10) 0.0341(10) 0.0755(16) -0.0001(10) 0.0057(11) -0.0079(8) O7 0.0366(10) 0.0283(9) 0.0783(15) 0.0038(11) 0.0099(12) 0.0026(7) O8 0.0258(9) 0.0500(12) 0.0646(14) 0.0046(11) 0.0033(9) -0.0062(8) N8 0.0446(14) 0.0339(12) 0.0602(16) -0.0002(13) 0.0028(14) 0.0110(10) C20 0.0241(10) 0.0345(12) 0.0348(12) -0.0014(11) 0.0007(10) 0.0003(9) C21 0.0254(11) 0.0417(13) 0.0377(14) 0.0022(12) -0.0023(10) -0.0026(10) C22 0.0254(11) 0.0465(16) 0.0400(14) 0.0009(12) 0.0011(11) 0.0084(10) C23 0.0343(12) 0.0359(12) 0.0357(12) -0.0016(12) -0.0003(12) 0.0090(10) C24 0.0302(12) 0.0321(13) 0.0403(15) -0.0010(12) 0.0007(11) 0.0013(10) C25 0.0274(12) 0.0337(12) 0.0390(15) -0.0017(11) 0.0025(11) 0.0004(9) C26 0.0328(12) 0.0311(12) 0.0443(15) -0.0036(12) 0.0007(12) -0.0035(9) O1 0.0305(9) 0.0414(11) 0.0783(16) 0.0077(12) 0.0073(11) 0.0063(8) N1 0.0343(11) 0.0347(11) 0.0478(14) 0.0009(11) 0.0011(10) -0.0008(9) N2 0.0290(11) 0.0310(11) 0.082(2) 0.0012(13) 0.0057(14) 0.0025(9) N3 0.0425(13) 0.0324(12) 0.097(3) 0.0035(16) 0.0060(19) -0.0012(10) C1 0.0315(12) 0.0398(14) 0.0460(16) 0.0038(13) -0.0020(11) 0.0029(10) C2 0.0280(11) 0.0363(14) 0.0404(16) 0.0000(12) -0.0024(11) -0.0010(10) C3 0.0261(11) 0.0359(12) 0.0325(12) -0.0003(11) 0.0034(10) 0.0003(9) C4 0.0266(11) 0.0442(14) 0.0422(14) 0.0014(12) 0.0009(11) 0.0017(10) C5 0.0304(13) 0.0376(13) 0.0492(16) -0.0033(13) 0.0005(12) -0.0035(11) C6 0.0288(11) 0.0333(12) 0.0440(15) 0.0023(12) 0.0058(11) 0.0035(9) O2 0.0301(9) 0.0396(10) 0.0815(16) 0.0040(12) -0.0032(11) -0.0093(8) N4 0.0349(11) 0.0283(10) 0.0474(13) 0.0022(10) -0.0055(11) -0.0029(8) N5 0.0330(11) 0.0268(10) 0.0582(15) -0.0005(11) -0.0054(11) -0.0037(8) N6 0.0480(14) 0.0261(11) 0.071(2) 0.0008(13) -0.0027(15) -0.0034(9) C7 0.0289(12) 0.0345(13) 0.0460(15) 0.0046(12) 0.0013(11) -0.0032(10) C8 0.0282(12) 0.0339(14) 0.0372(15) -0.0003(11) -0.0001(10) -0.0012(10) C9 0.0279(11) 0.0286(11) 0.0337(12) 0.0006(11) -0.0038(10) -0.0042(8) C10 0.0248(11) 0.0359(13) 0.0398(14) -0.0011(11) -0.0022(10) -0.0034(9) C11 0.0298(12) 0.0337(12) 0.0469(15) -0.0022(12) -0.0038(11) 0.0020(10) C12 0.0324(12) 0.0318(12) 0.0400(14) 0.0007(12) -0.0031(11) -0.0047(9) #=============================================================================== _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; 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 O3 C19 1.236(3) . . yes O4 C19 1.307(3) . . yes O5 C14 1.365(3) . . yes O4 H4O 1.01(5) . . no O5 H5O 0.94(3) . . no O6 C26 1.250(3) . . yes O7 C26 1.294(3) . . yes O8 C21 1.364(3) . . yes O7 H7O 1.01(7) . . no O8 H8O 0.98(7) . . no O1 C6 1.220(3) . . yes O2 C12 1.225(3) . . yes N7 C16 1.371(4) . . yes N7 H7A 0.88(4) . . no N7 H7B 0.98(4) . . no N8 C23 1.369(3) . . yes N8 H8B 1.03(4) . . no N8 H8A 0.85(4) . . no N1 C5 1.341(4) . . yes N1 C1 1.330(4) . . yes N2 C6 1.334(3) . . yes N2 N3 1.414(3) . . yes N2 H2N 0.82(4) . . no N3 H3B 0.98(5) . . no N3 H3A 0.92(5) . . no N4 C11 1.344(3) . . yes N4 C7 1.333(3) . . yes N5 C12 1.326(3) . . yes N5 N6 1.423(3) . . yes N5 H5N 0.91(4) . . no N6 H6A 0.94(4) . . no N6 H6B 0.90(7) . . no C13 C14 1.407(3) . . no C13 C19 1.464(4) . . no C13 C18 1.400(4) . . no C14 C15 1.381(4) . . no C15 C16 1.394(4) . . no C16 C17 1.410(4) . . no C17 C18 1.381(4) . . no C15 H15 0.99(3) . . no C17 H17 0.95(3) . . no C18 H18 1.00(3) . . no C20 C26 1.474(3) . . no C20 C25 1.399(4) . . no C20 C21 1.404(3) . . no C21 C22 1.390(4) . . no C22 C23 1.396(4) . . no C23 C24 1.412(4) . . no C24 C25 1.368(4) . . no C22 H22 0.87(3) . . no C24 H24 0.89(3) . . no C25 H25 0.97(3) . . no C1 C2 1.384(4) . . no C2 C3 1.390(3) . . no C3 C4 1.390(4) . . no C3 C6 1.497(3) . . no C4 C5 1.382(4) . . no C1 H1 1.03(3) . . no C2 H2 0.91(4) . . no C4 H4 0.99(3) . . no C5 H5 0.94(3) . . no C7 C8 1.390(4) . . no C8 C9 1.383(4) . . no C9 C10 1.378(4) . . no C9 C12 1.515(3) . . no C10 C11 1.388(4) . . no C7 H7 0.85(3) . . no C8 H8 0.92(3) . . no C10 H10 1.01(3) . . no C11 H11 1.05(3) . . 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 C19 O4 H4O 115(3) . . . no C14 O5 H5O 103(2) . . . no C26 O7 H7O 115(4) . . . no C21 O8 H8O 95(4) . . . no C16 N7 H7A 118(2) . . . no H7A N7 H7B 115(3) . . . no C16 N7 H7B 119(2) . . . no C23 N8 H8B 119.1(19) . . . no C23 N8 H8A 118(2) . . . no H8A N8 H8B 121(3) . . . no C1 N1 C5 118.5(2) . . . yes N3 N2 C6 122.5(2) . . . yes N3 N2 H2N 115(2) . . . no C6 N2 H2N 122(2) . . . no H3A N3 H3B 105(4) . . . no N2 N3 H3A 105(3) . . . no N2 N3 H3B 107(3) . . . no C7 N4 C11 118.8(2) . . . yes N6 N5 C12 122.2(2) . . . yes C12 N5 H5N 127(2) . . . no N6 N5 H5N 111(2) . . . no N5 N6 H6B 109(4) . . . no N5 N6 H6A 112(3) . . . no H6A N6 H6B 110(5) . . . no C14 C13 C18 117.7(2) . . . no C18 C13 C19 121.5(2) . . . no C14 C13 C19 120.8(2) . . . no O5 C14 C15 118.5(2) . . . yes C13 C14 C15 120.8(2) . . . no O5 C14 C13 120.7(2) . . . yes C14 C15 C16 121.0(2) . . . no C15 C16 C17 118.9(2) . . . no N7 C16 C15 120.9(2) . . . yes N7 C16 C17 120.3(2) . . . yes C16 C17 C18 119.7(2) . . . no C13 C18 C17 121.9(2) . . . no O4 C19 C13 115.2(2) . . . yes O3 C19 C13 122.1(2) . . . yes O3 C19 O4 122.7(2) . . . yes C16 C15 H15 121.8(16) . . . no C14 C15 H15 117.1(16) . . . no C18 C17 H17 120.5(16) . . . no C16 C17 H17 119.8(16) . . . no C13 C18 H18 113.6(15) . . . no C17 C18 H18 124.3(16) . . . no C25 C20 C26 121.8(2) . . . no C21 C20 C26 120.2(2) . . . no C21 C20 C25 118.0(2) . . . no O8 C21 C22 118.8(2) . . . yes C20 C21 C22 120.1(2) . . . no O8 C21 C20 121.1(2) . . . yes C21 C22 C23 121.2(2) . . . no N8 C23 C22 121.8(2) . . . yes N8 C23 C24 119.8(2) . . . yes C22 C23 C24 118.4(2) . . . no C23 C24 C25 120.0(2) . . . no C20 C25 C24 122.1(2) . . . no O7 C26 C20 116.3(2) . . . yes O6 C26 O7 122.5(2) . . . yes O6 C26 C20 121.2(2) . . . yes C21 C22 H22 123(2) . . . no C23 C22 H22 116(2) . . . no C25 C24 H24 118(2) . . . no C23 C24 H24 122(2) . . . no C20 C25 H25 116.9(19) . . . no C24 C25 H25 120.9(19) . . . no N1 C1 C2 123.2(2) . . . yes C1 C2 C3 118.4(2) . . . no C2 C3 C6 123.6(2) . . . no C2 C3 C4 118.5(2) . . . no C4 C3 C6 117.9(2) . . . no C3 C4 C5 119.2(2) . . . no N1 C5 C4 122.2(3) . . . yes N2 C6 C3 116.2(2) . . . yes O1 C6 C3 121.2(2) . . . yes O1 C6 N2 122.5(2) . . . yes N1 C1 H1 107.8(19) . . . no C2 C1 H1 129.0(19) . . . no C3 C2 H2 123(2) . . . no C1 C2 H2 119(2) . . . no C3 C4 H4 117.8(19) . . . no C5 C4 H4 123.0(19) . . . no N1 C5 H5 116(2) . . . no C4 C5 H5 122(2) . . . no N4 C7 C8 122.7(2) . . . yes C7 C8 C9 118.4(2) . . . no C8 C9 C10 119.1(2) . . . no C10 C9 C12 118.4(2) . . . no C8 C9 C12 122.6(2) . . . no C9 C10 C11 119.4(2) . . . no N4 C11 C10 121.7(2) . . . yes O2 C12 C9 120.3(2) . . . yes N5 C12 C9 115.6(2) . . . yes O2 C12 N5 124.2(2) . . . yes N4 C7 H7 119.3(18) . . . no C8 C7 H7 117.9(18) . . . no C7 C8 H8 123(2) . . . no C9 C8 H8 119(2) . . . no C9 C10 H10 121.3(19) . . . no C11 C10 H10 118.9(19) . . . no N4 C11 H11 113.3(16) . . . no C10 C11 H11 125.0(17) . . . 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N1 C5 C4 -0.4(5) . . . . no C5 N1 C1 C2 -0.1(5) . . . . no N3 N2 C6 C3 -178.8(4) . . . . no N3 N2 C6 O1 0.3(6) . . . . no C11 N4 C7 C8 -1.3(4) . . . . no C7 N4 C11 C10 1.0(4) . . . . no N6 N5 C12 C9 -177.5(3) . . . . no N6 N5 C12 O2 1.5(5) . . . . no C14 C13 C18 C17 -0.6(4) . . . . no C19 C13 C18 C17 178.2(3) . . . . no C19 C13 C14 O5 1.3(4) . . . . no C14 C13 C19 O4 169.8(3) . . . . no C18 C13 C19 O4 -8.9(4) . . . . no C14 C13 C19 O3 -9.2(5) . . . . no C18 C13 C14 O5 -180.0(3) . . . . no C19 C13 C14 C15 -177.9(3) . . . . no C18 C13 C14 C15 0.8(4) . . . . no C18 C13 C19 O3 172.1(3) . . . . no C13 C14 C15 C16 0.3(4) . . . . no O5 C14 C15 C16 -178.9(3) . . . . no C14 C15 C16 C17 -1.6(4) . . . . no C14 C15 C16 N7 -179.4(3) . . . . no C15 C16 C17 C18 1.9(4) . . . . no N7 C16 C17 C18 179.7(3) . . . . no C16 C17 C18 C13 -0.8(4) . . . . no C26 C20 C21 C22 174.0(3) . . . . no C25 C20 C26 O7 -1.8(4) . . . . no C26 C20 C21 O8 -5.1(4) . . . . no C25 C20 C21 C22 -4.0(4) . . . . no C26 C20 C25 C24 -174.4(3) . . . . no C21 C20 C26 O6 -1.0(4) . . . . no C21 C20 C25 C24 3.6(4) . . . . no C25 C20 C26 O6 176.9(3) . . . . no C25 C20 C21 O8 176.9(3) . . . . no C21 C20 C26 O7 -179.7(3) . . . . no O8 C21 C22 C23 -179.9(3) . . . . no C20 C21 C22 C23 0.9(4) . . . . no C21 C22 C23 C24 2.6(4) . . . . no C21 C22 C23 N8 -179.3(3) . . . . no N8 C23 C24 C25 178.8(3) . . . . no C22 C23 C24 C25 -3.0(4) . . . . no C23 C24 C25 C20 -0.1(4) . . . . no N1 C1 C2 C3 0.2(4) . . . . no C1 C2 C3 C4 0.3(4) . . . . no C1 C2 C3 C6 179.9(3) . . . . no C4 C3 C6 O1 24.8(4) . . . . no C2 C3 C4 C5 -0.8(4) . . . . no C4 C3 C6 N2 -156.0(3) . . . . no C2 C3 C6 N2 24.3(4) . . . . no C6 C3 C4 C5 179.6(3) . . . . no C2 C3 C6 O1 -154.8(3) . . . . no C3 C4 C5 N1 0.8(5) . . . . no N4 C7 C8 C9 0.5(4) . . . . no C7 C8 C9 C10 0.7(4) . . . . no C7 C8 C9 C12 178.8(3) . . . . no C8 C9 C12 N5 27.5(4) . . . . no C10 C9 C12 O2 26.5(4) . . . . no C10 C9 C12 N5 -154.4(3) . . . . no C8 C9 C12 O2 -151.6(3) . . . . no C8 C9 C10 C11 -1.0(4) . . . . no C12 C9 C10 C11 -179.2(3) . . . . no C9 C10 C11 N4 0.1(4) . . . . 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 O1 C7 3.372(3) . . no O1 N6 3.020(4) . 3_554 no O1 O6 3.206(4) . 3_555 no O1 N3 2.754(3) . . no O2 N6 2.779(3) . . no O2 O8 3.130(4) . . no O2 N3 3.052(4) . 3_545 no O3 N8 3.068(3) . 3_544 no O3 C1 3.327(3) . 2_654 no O3 O5 2.588(3) . . no O4 C1 3.399(3) . 2_654 no O4 N1 2.583(3) . 2_654 no O5 O3 2.588(3) . . no O5 N5 3.044(3) . 1_554 no O6 O8 2.558(3) . . no O6 O1 3.206(4) . 3_544 no O6 N7 3.024(3) . 3_545 no O7 N4 2.560(3) . 3_544 no O8 O2 3.130(4) . . no O8 O6 2.558(3) . . no O8 N2 3.029(3) . 4_455 no O1 H3B 2.68(5) . . no O1 H3A 2.62(5) . . no O1 H7 2.52(3) . . no O1 H6A 2.12(5) . 3_554 no O1 H4 2.51(3) . . no O2 H2 2.91(3) . 4_455 no O2 H6B 2.86(7) . . no O2 H10 2.62(3) . . no O2 H3B 2.17(5) . 3_545 no O2 H6A 2.72(5) . . no O3 H1 2.59(3) . 2_654 no O3 H5O 1.71(3) . . no O3 H8A 2.31(4) . 3_544 no O4 H11 2.61(3) . 4_554 no O4 H18 2.36(3) . . no O5 H5N 2.15(4) . 1_554 no O5 H25 2.79(4) . . no O6 H6B 2.50(7) . . no O6 H8O 1.61(7) . . no O6 H7B 2.15(4) . 3_545 no O7 H5 2.70(3) . . no O7 H25 2.44(3) . . no O8 H3A 2.66(5) . 3_544 no O8 H2N 2.26(5) . 4_455 no O8 H17 2.92(3) . 4_455 no N1 O4 2.583(3) . 2_655 no N1 C19 3.330(3) . 2_655 no N2 O8 3.029(3) . 4_555 no N3 N7 3.111(4) . 2_665 no N3 O2 3.052(4) . 3_554 no N3 O1 2.754(3) . . no N4 C26 3.309(3) . 3_555 no N4 O7 2.560(3) . 3_555 no N5 O5 3.044(3) . 1_556 no N6 N8 3.170(4) . 3_545 no N6 O1 3.020(4) . 3_545 no N6 O2 2.779(3) . . no N7 O6 3.024(3) . 3_554 no N7 N3 3.111(4) . 2_664 no N8 C11 3.325(4) . 1_554 no N8 N6 3.170(4) . 3_554 no N8 O3 3.068(3) . 3_555 no N1 H4O 1.58(5) . 2_655 no N2 H2 2.70(3) . . no N3 H7A 2.24(4) . 2_665 no N4 H7O 1.55(7) . 3_555 no N5 H8 2.61(3) . . no N6 H8B 2.17(4) . 3_545 no C1 C18 3.589(4) . 1_556 no C1 O4 3.399(3) . 2_655 no C1 C13 3.357(4) . 1_556 no C1 O3 3.327(3) . 2_655 no C2 C17 3.567(4) . 1_556 no C3 C15 3.453(4) . 1_556 no C3 C17 3.456(4) . . no C3 C16 3.565(4) . 1_556 no C4 C25 3.579(4) . . no C4 C17 3.554(4) . . no C5 C13 3.451(5) . . no C5 C18 3.583(4) . . no C7 O1 3.372(3) . . no C7 C23 3.436(4) . . no C7 C24 3.556(4) . . no C8 C24 3.515(4) . . no C8 C25 3.572(4) . . no C8 C23 3.508(4) . . no C9 C22 3.576(4) . . no C9 C21 3.555(4) . . no C10 C18 3.597(4) . 4_456 no C10 C23 3.379(4) . 1_556 no C10 C22 3.467(4) . 1_556 no C11 C23 3.376(4) . 1_556 no C11 N8 3.325(4) . 1_556 no C12 C21 3.519(4) . . no C13 C5 3.451(5) . . no C13 C1 3.357(4) . 1_554 no C15 C3 3.453(4) . 1_554 no C15 C25 3.550(4) . . no C16 C3 3.565(4) . 1_554 no C17 C4 3.554(4) . . no C17 C3 3.456(4) . . no C17 C2 3.567(4) . 1_554 no C18 C5 3.583(4) . . no C18 C10 3.597(4) . 4_554 no C18 C1 3.589(4) . 1_554 no C19 N1 3.330(3) . 2_654 no C21 C9 3.555(4) . . no C21 C12 3.519(4) . . no C22 C9 3.576(4) . . no C22 C10 3.467(4) . 1_554 no C23 C8 3.508(4) . . no C23 C11 3.376(4) . 1_554 no C23 C7 3.436(4) . . no C23 C10 3.379(4) . 1_554 no C24 C7 3.556(4) . . no C24 C8 3.515(4) . . no C25 C8 3.572(4) . . no C25 C4 3.579(4) . . no C25 C15 3.550(4) . . no C26 N4 3.309(3) . 3_544 no C1 H4O 2.50(5) . 2_655 no C1 H22 2.94(3) . 4_555 no C2 H2N 2.63(4) . . no C2 H22 2.90(3) . 4_555 no C4 H25 3.01(3) . . no C5 H4O 2.56(5) . 2_655 no C7 H7O 2.50(7) . 3_555 no C7 H15 2.77(3) . 1_556 no C8 H15 2.70(3) . 1_556 no C8 H5N 2.68(3) . . no C10 H2 3.02(4) . 4_455 no C11 H7O 2.52(7) . 3_555 no C11 H1 2.91(3) . 4_455 no C14 H25 2.87(3) . . no C15 H25 2.90(3) . . no C17 H10 2.92(3) . 4_554 no C18 H10 2.73(3) . 4_554 no C19 H5O 2.25(4) . . no C22 H18 2.95(3) . 4_455 no C22 H10 3.09(4) . 1_554 no C24 H4 2.94(4) . . no C25 H4 2.81(4) . . no C26 H8O 2.12(7) . . no H1 C11 2.91(3) . 4_555 no H1 H4O 2.44(6) . 2_655 no H1 O3 2.59(3) . 2_655 no H2 N2 2.70(3) . . no H2 O2 2.91(3) . 4_555 no H2 H2N 2.26(5) . . no H2 C10 3.02(4) . 4_555 no H2N H2 2.26(5) . . no H2N C2 2.63(4) . . no H2N O8 2.26(5) . 4_555 no H3A O8 2.66(5) . 3_555 no H3A H8O 2.50(9) . 3_555 no H3A O1 2.62(5) . . no H3B O2 2.17(5) . 3_554 no H3B O1 2.68(5) . . no H4 C25 2.81(4) . . no H4 C24 2.94(4) . . no H4 H25 2.41(5) . . no H4 O1 2.51(3) . . no H4O N1 1.58(5) . 2_654 no H4O C1 2.50(5) . 2_654 no H4O C5 2.56(5) . 2_654 no H4O H1 2.44(6) . 2_654 no H5 O7 2.70(3) . . no H5N C8 2.68(3) . . no H5N H5O 2.59(5) . 1_556 no H5N O5 2.15(4) . 1_556 no H5N H8 2.23(5) . . no H5O O3 1.71(3) . . no H5O H5N 2.59(5) . 1_554 no H5O C19 2.25(4) . . no H6A O1 2.12(5) . 3_545 no H6A O2 2.72(5) . . no H6B O6 2.50(7) . . no H6B O2 2.86(7) . . no H6B H8B 2.40(8) . 3_545 no H7 H7O 2.60(7) . 3_555 no H7 O1 2.52(3) . . no H7A H17 2.42(5) . . no H7A N3 2.24(4) . 2_664 no H7B H15 2.46(4) . . no H7B O6 2.15(4) . 3_554 no H7O H11 2.58(7) . 3_544 no H7O C11 2.52(7) . 3_544 no H7O C7 2.50(7) . 3_544 no H7O H7 2.60(7) . 3_544 no H7O N4 1.55(7) . 3_544 no H8 H5N 2.23(5) . . no H8 H15 2.58(5) . 1_556 no H8 N5 2.61(3) . . no H8A H22 2.36(5) . . no H8A O3 2.31(4) . 3_555 no H8B N6 2.17(4) . 3_554 no H8B H6B 2.40(8) . 3_554 no H8B H24 2.42(5) . . no H8O O6 1.61(7) . . no H8O C26 2.12(7) . . no H8O H3A 2.50(9) . 3_544 no H10 O2 2.62(3) . . no H10 C17 2.92(3) . 4_456 no H10 C18 2.73(3) . 4_456 no H10 C22 3.09(4) . 1_556 no H10 H18 2.44(4) . 4_456 no H11 H7O 2.58(7) . 3_555 no H11 O4 2.61(3) . 4_456 no H15 C8 2.70(3) . 1_554 no H15 H7B 2.46(4) . . no H15 C7 2.77(3) . 1_554 no H15 H8 2.58(5) . 1_554 no H17 O8 2.92(3) . 4_555 no H17 H7A 2.42(5) . . no H18 H10 2.44(4) . 4_554 no H18 H22 2.38(4) . 4_555 no H18 C22 2.95(3) . 4_555 no H18 O4 2.36(3) . . no H22 C2 2.90(3) . 4_455 no H22 H18 2.38(4) . 4_455 no H22 C1 2.94(3) . 4_455 no H22 H8A 2.36(5) . . no H24 H8B 2.42(5) . . no H25 H4 2.41(5) . . no H25 O5 2.79(4) . . no H25 O7 2.44(3) . . no H25 C4 3.01(3) . . no H25 C14 2.87(3) . . no H25 C15 2.90(3) . . no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # N2 H2N O8 0.82(4) 2.26(5) 3.029(3) 156(5) 4_555 yes N3 H3B O2 0.98(5) 2.17(5) 3.052(4) 149(4) 3_554 yes O4 H4O N1 1.01(5) 1.58(5) 2.583(3) 175(4) 2_654 yes N5 H5N O5 0.91(4) 2.15(4) 3.044(3) 170(3) 1_556 yes O5 H5O O3 0.94(3) 1.71(3) 2.588(3) 154(3) . yes N6 H6A O1 0.94(4) 2.12(5) 3.020(4) 160(4) 3_545 yes N6 H6B O6 0.90(7) 2.50(7) 3.315(5) 150(6) . yes N7 H7A N3 0.88(4) 2.24(4) 3.111(4) 170(4) 2_664 yes N7 H7B O6 0.98(4) 2.15(4) 3.024(3) 149(3) 3_554 yes O7 H7O N4 1.01(7) 1.55(7) 2.560(3) 178(10) 3_544 yes N8 H8A O3 0.85(4) 2.31(4) 3.068(3) 149(3) 3_555 yes N8 H8B N6 1.03(4) 2.17(4) 3.170(4) 165(3) 3_554 yes O8 H8O O6 0.98(7) 1.61(7) 2.558(3) 163(6) . yes C1 H1 O3 1.03(3) 2.59(3) 3.327(3) 129(3) 2_655 yes C7 H7 O1 0.85(3) 2.52(3) 3.372(3) 174(3) . yes C18 H18 O4 1.00(3) 2.36(3) 2.758(3) 102.8(18) . yes C25 H25 O7 0.97(3) 2.44(3) 2.785(3) 101(2) . yes #===END # Attachment '3093_web_deposit_cif_file_7_PawelGrobelny_1289286463.cif' # CIF-file generated for datam in Pna2(1) #=============================================================================== data_datam8 _database_code_depnum_ccdc_archive 'CCDC 800237' #TrackingRef '3093_web_deposit_cif_file_7_PawelGrobelny_1289286463.cif' #=============================================================================== _chemical_name_systematic ; ; _chemical_name_common 'Isoniazid:4-aminosalicylic acid co-crystal' _chemical_melting_point ? _chemical_formula_moiety 'C7 H7 N O3, C6 H7 N3 O' _chemical_formula_structural ? _chemical_formula_sum 'C13 H14 N4 O4' _chemical_formula_iupac ? _chemical_formula_weight 290.28 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_space_group_name_H-M 'P n a 21' _symmetry_Int_Tables_number 33 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,1/2+z 3 1/2-x,1/2+y,1/2+z 4 1/2+x,1/2-y,z _cell_length_a 21.926(10) _cell_length_b 16.514(8) _cell_length_c 7.310(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2647(2) _cell_formula_units_Z 8 _cell_measurement_temperature 240(2) _cell_measurement_reflns_used 6328 _cell_measurement_theta_min 1.9 _cell_measurement_theta_max 27.5 _cell_special_details ; ; _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.457 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 0.111 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.791 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' #=============================================================================== _exptl_special_details ; ; _diffrn_ambient_temperature 240 _diffrn_source_power 0.6 _diffrn_source_voltage 50.0 _diffrn_source_current 12.0 _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_source 'Sealed Tube' _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_measurement_specimen_support Fiber _diffrn_detector CCD _diffrn_measurement_device ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_detector_area_resol_mean 13.6612 _diffrn_measurement_method 'profile data from \w-scans' _diffrn_reflns_number 27304 _diffrn_reflns_av_R_equivalents 0.0522 _diffrn_reflns_av_sigmaI/netI 0.0240 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3277 _reflns_number_gt 3060 _reflns_threshold_expression >2\s(I) _diffrn_measurement_details ; scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 0.0000 XTD: 49.3989 2theta: 29.5608 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 120.0000 XTD: 49.3989 2theta: 29.5608 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 240.0000 XTD: 49.3989 2theta: 29.5608 ; _diffrn_orient_matrix_UB_11 0.014928 _diffrn_orient_matrix_UB_12 -0.134957 _diffrn_orient_matrix_UB_13 0.016743 _diffrn_orient_matrix_UB_21 0.060121 _diffrn_orient_matrix_UB_22 0.006913 _diffrn_orient_matrix_UB_23 0.002121 _diffrn_orient_matrix_UB_31 -0.002213 _diffrn_orient_matrix_UB_32 0.005367 _diffrn_orient_matrix_UB_33 0.045237 _diffrn_orient_matrix_type d*Trek _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.999 _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement ? _computing_molecular_graphics ? _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== _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^ > 2\s(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^)+(0.0750P)^2^+0.2991P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3277 _refine_ls_number_parameters 492 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0498 _refine_ls_R_factor_gt 0.0440 _refine_ls_wR_factor_ref 0.1305 _refine_ls_wR_factor_gt 0.1196 _refine_ls_goodness_of_fit_ref 1.160 _refine_ls_restrained_S_all 1.160 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 #=============================================================================== loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags O3 O Uani 0.42376(10) 0.00397(12) 0.3898(5) 1.000 0.0542(8) . . O4 O Uani 0.52045(9) 0.03779(12) 0.4471(5) 1.000 0.0512(7) . . O5 O Uani 0.34695(9) 0.11807(13) 0.3121(5) 1.000 0.0461(7) . . N7 N Uani 0.40860(14) 0.39074(16) 0.4169(5) 1.000 0.0514(9) . . C13 C Uani 0.44870(12) 0.14244(16) 0.4226(4) 1.000 0.0332(7) . . C14 C Uani 0.39123(12) 0.17064(17) 0.3678(4) 1.000 0.0346(8) . . C15 C Uani 0.37801(12) 0.25254(17) 0.3653(4) 1.000 0.0358(8) . . C16 C Uani 0.42200(12) 0.30956(16) 0.4178(4) 1.000 0.0361(8) . . C17 C Uani 0.47937(12) 0.28183(17) 0.4776(4) 1.000 0.0365(8) . . C18 C Uani 0.49205(11) 0.20023(17) 0.4781(4) 1.000 0.0343(8) . . C19 C Uani 0.46323(12) 0.05578(17) 0.4200(5) 1.000 0.0397(8) . . O6 O Uani 0.18298(10) 0.00771(13) 0.7564(5) 1.000 0.0530(8) . . O7 O Uani 0.27818(9) 0.03853(12) 0.6752(5) 1.000 0.0513(8) . . O8 O Uani 0.10161(9) 0.11914(15) 0.7645(5) 1.000 0.0507(7) . . N8 N Uani 0.16817(14) 0.39318(16) 0.6937(5) 1.000 0.0504(9) . . C20 C Uani 0.20708(11) 0.14506(15) 0.6919(4) 1.000 0.0334(7) . . C21 C Uani 0.14761(12) 0.17245(18) 0.7280(4) 1.000 0.0365(8) . . C22 C Uani 0.13482(13) 0.25487(19) 0.7285(5) 1.000 0.0390(8) . . C23 C Uani 0.17998(12) 0.31157(16) 0.6916(4) 1.000 0.0370(8) . . C24 C Uani 0.23897(13) 0.28401(17) 0.6465(4) 1.000 0.0368(9) . . C25 C Uani 0.25136(12) 0.20273(16) 0.6471(4) 1.000 0.0344(8) . . C26 C Uani 0.22203(13) 0.05848(16) 0.7094(4) 1.000 0.0392(8) . . O1 O Uani 0.37656(9) 0.39824(13) 0.9400(5) 1.000 0.0531(8) . . N1 N Uani 0.45707(11) 0.11552(14) 0.9349(4) 1.000 0.0408(7) . . N2 N Uani 0.47719(11) 0.41946(15) 0.9249(5) 1.000 0.0506(9) . . N3 N Uani 0.47275(14) 0.50504(16) 0.9247(8) 1.000 0.0612(12) . . C1 C Uani 0.50086(13) 0.16497(18) 0.9941(5) 1.000 0.0417(9) . . C2 C Uani 0.49501(12) 0.24826(18) 0.9966(5) 1.000 0.0374(9) . . C3 C Uani 0.44043(11) 0.28227(15) 0.9360(4) 1.000 0.0327(7) . . C4 C Uani 0.39447(13) 0.2309(2) 0.8762(5) 1.000 0.0392(8) . . C5 C Uani 0.40442(13) 0.14862(19) 0.8772(5) 1.000 0.0416(9) . . C6 C Uani 0.42840(12) 0.37152(17) 0.9335(5) 1.000 0.0382(8) . . O2 O Uani 0.11415(10) 0.10657(13) 0.1917(5) 1.000 0.0539(8) . . N4 N Uani 0.20132(11) 0.38558(14) 0.1836(4) 1.000 0.0399(7) . . N5 N Uani 0.21514(11) 0.08178(14) 0.2058(4) 1.000 0.0430(8) . . N6 N Uani 0.20954(14) -0.00388(15) 0.2049(6) 1.000 0.0517(9) . . C7 C Uani 0.24299(13) 0.33406(18) 0.1198(5) 1.000 0.0388(8) . . C8 C Uani 0.23486(12) 0.25045(17) 0.1216(4) 1.000 0.0346(8) . . C9 C Uani 0.18094(11) 0.22011(15) 0.1919(4) 1.000 0.0327(7) . . C10 C Uani 0.13724(12) 0.27349(18) 0.2554(4) 1.000 0.0357(8) . . C11 C Uani 0.14882(12) 0.35626(18) 0.2500(5) 1.000 0.0396(8) . . C12 C Uani 0.16704(12) 0.13054(16) 0.1971(5) 1.000 0.0360(8) . . H4O H Uiso 0.532(2) -0.022(3) 0.436(10) 1.000 0.101(17) . . H5O H Uiso 0.3648(19) 0.068(2) 0.329(7) 1.000 0.069(13) . . H7A H Uiso 0.4386(17) 0.426(2) 0.422(7) 1.000 0.056(11) . . H7B H Uiso 0.375(2) 0.409(3) 0.344(9) 1.000 0.098(18) . . H15 H Uiso 0.3364(16) 0.270(2) 0.328(5) 1.000 0.048(9) . . H17 H Uiso 0.5099(13) 0.3190(17) 0.509(4) 1.000 0.026(7) . . H18 H Uiso 0.5289(12) 0.1758(16) 0.526(4) 1.000 0.024(7) . . H7O H Uiso 0.285(2) -0.022(3) 0.675(10) 1.000 0.106(18) . . H8A H Uiso 0.137(2) 0.412(3) 0.737(7) 1.000 0.067(13) . . H8B H Uiso 0.2029(17) 0.430(2) 0.684(6) 1.000 0.051(10) . . H8O H Uiso 0.127(2) 0.073(3) 0.764(9) 1.000 0.103(19) . . H22 H Uiso 0.0999(17) 0.274(2) 0.759(6) 1.000 0.052(10) . . H24 H Uiso 0.2699(18) 0.320(3) 0.629(7) 1.000 0.068(13) . . H25 H Uiso 0.2926(14) 0.1840(18) 0.623(5) 1.000 0.039(9) . . H1 H Uiso 0.5371(14) 0.128(2) 1.032(5) 1.000 0.040(9) . . H2 H Uiso 0.5272(16) 0.280(2) 1.032(6) 1.000 0.053(11) . . H2N H Uiso 0.513(2) 0.405(3) 0.909(8) 1.000 0.074(14) . . H3A H Uiso 0.442(3) 0.520(4) 0.828(8) 1.000 0.085(16) . . H3B H Uiso 0.453(3) 0.517(4) 1.031(10) 1.000 0.10(2) . . H4 H Uiso 0.3560(17) 0.255(2) 0.833(6) 1.000 0.055(11) . . H5 H Uiso 0.3750(17) 0.110(2) 0.834(6) 1.000 0.051(10) . . H5N H Uiso 0.256(2) 0.099(3) 0.219(8) 1.000 0.085(15) . . H6A H Uiso 0.183(2) -0.022(3) 0.300(8) 1.000 0.076(14) . . H6B H Uiso 0.194(3) -0.019(3) 0.093(9) 1.000 0.084(17) . . H7 H Uiso 0.2766(14) 0.3506(18) 0.071(5) 1.000 0.031(8) . . H8 H Uiso 0.2644(17) 0.215(2) 0.066(6) 1.000 0.053(11) . . H10 H Uiso 0.0994(16) 0.254(2) 0.316(5) 1.000 0.046(10) . . H11 H Uiso 0.1189(15) 0.398(2) 0.302(5) 1.000 0.041(9) . . 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 O3 0.0359(10) 0.0358(10) 0.091(2) -0.0076(12) -0.0056(12) -0.0051(8) O4 0.0314(9) 0.0356(10) 0.0865(18) 0.0006(12) -0.0051(12) 0.0006(8) O5 0.0292(9) 0.0422(11) 0.0669(14) -0.0022(11) -0.0080(10) -0.0063(8) N7 0.0487(15) 0.0325(12) 0.073(2) 0.0002(14) -0.0086(16) 0.0006(11) C13 0.0287(11) 0.0324(12) 0.0384(13) -0.0016(12) 0.0009(11) -0.0034(10) C14 0.0273(12) 0.0408(14) 0.0356(13) -0.0018(12) 0.0015(11) -0.0063(10) C15 0.0257(11) 0.0390(14) 0.0427(16) 0.0018(12) 0.0000(11) -0.0010(10) C16 0.0359(13) 0.0365(13) 0.0358(14) 0.0007(12) 0.0015(12) 0.0006(10) C17 0.0312(12) 0.0367(14) 0.0417(15) -0.0024(13) -0.0012(12) -0.0063(10) C18 0.0258(12) 0.0395(13) 0.0376(15) -0.0013(12) -0.0015(11) -0.0023(10) C19 0.0337(13) 0.0354(13) 0.0499(16) -0.0007(14) -0.0001(13) -0.0024(10) O6 0.0409(11) 0.0351(10) 0.0830(18) -0.0002(11) 0.0070(12) -0.0098(8) O7 0.0395(11) 0.0282(9) 0.0863(18) 0.0035(12) 0.0116(13) 0.0030(7) O8 0.0271(9) 0.0527(13) 0.0722(16) 0.0068(12) 0.0030(10) -0.0057(9) N8 0.0492(16) 0.0367(13) 0.0654(18) -0.0043(14) 0.0038(15) 0.0129(12) C20 0.0261(11) 0.0361(13) 0.0381(13) -0.0015(12) -0.0014(10) 0.0006(10) C21 0.0277(12) 0.0434(14) 0.0383(15) 0.0019(12) -0.0030(11) -0.0033(10) C22 0.0280(12) 0.0468(16) 0.0423(15) 0.0002(13) 0.0017(12) 0.0087(11) C23 0.0384(14) 0.0371(13) 0.0355(13) -0.0005(12) -0.0009(12) 0.0081(11) C24 0.0319(13) 0.0335(14) 0.0451(17) 0.0000(13) 0.0023(12) 0.0004(10) C25 0.0286(12) 0.0335(13) 0.0411(16) -0.0023(12) 0.0018(11) 0.0000(10) C26 0.0353(14) 0.0335(13) 0.0487(16) -0.0029(13) 0.0006(13) -0.0040(10) O1 0.0324(10) 0.0438(11) 0.0831(18) 0.0081(13) 0.0073(12) 0.0072(8) N1 0.0357(12) 0.0365(12) 0.0502(14) 0.0016(12) 0.0023(11) -0.0012(9) N2 0.0303(12) 0.0345(12) 0.087(2) 0.0026(15) 0.0077(15) 0.0020(9) N3 0.0430(14) 0.0325(13) 0.108(3) 0.0050(18) 0.007(2) -0.0020(10) C1 0.0346(13) 0.0414(15) 0.0490(17) 0.0039(14) -0.0031(12) 0.0018(12) C2 0.0285(12) 0.0401(16) 0.0436(17) 0.0007(13) -0.0024(12) -0.0011(11) C3 0.0284(12) 0.0365(13) 0.0333(12) 0.0015(12) 0.0038(10) -0.0005(9) C4 0.0278(12) 0.0456(15) 0.0442(15) -0.0004(13) 0.0009(12) 0.0015(11) C5 0.0313(13) 0.0407(14) 0.0528(18) -0.0022(14) -0.0019(12) -0.0053(11) C6 0.0306(12) 0.0386(14) 0.0455(16) 0.0039(14) 0.0067(12) 0.0045(10) O2 0.0317(10) 0.0409(11) 0.0892(18) 0.0040(13) -0.0042(12) -0.0093(8) N4 0.0370(12) 0.0321(11) 0.0506(14) 0.0022(12) -0.0070(12) -0.0031(9) N5 0.0358(12) 0.0278(11) 0.0653(18) -0.0011(13) -0.0055(13) -0.0037(9) N6 0.0515(16) 0.0287(12) 0.075(2) 0.0013(14) -0.0051(17) -0.0030(10) C7 0.0298(13) 0.0371(14) 0.0494(16) 0.0049(13) 0.0025(12) -0.0042(11) C8 0.0302(13) 0.0358(15) 0.0377(16) -0.0005(12) -0.0006(11) -0.0004(11) C9 0.0284(12) 0.0323(12) 0.0373(13) -0.0014(12) -0.0044(11) -0.0044(9) C10 0.0256(11) 0.0396(14) 0.0418(15) -0.0006(12) -0.0008(11) -0.0026(10) C11 0.0313(13) 0.0366(14) 0.0508(16) -0.0029(13) -0.0029(12) 0.0018(11) C12 0.0343(13) 0.0317(12) 0.0419(14) 0.0005(12) -0.0027(12) -0.0022(10) #=============================================================================== _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; 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 O3 C19 1.237(4) . . yes O4 C19 1.304(3) . . yes O5 C14 1.365(4) . . yes O4 H4O 1.02(5) . . no O5 H5O 0.92(4) . . no O6 C26 1.247(4) . . yes O7 C26 1.299(4) . . yes O8 C21 1.365(4) . . yes O7 H7O 1.01(5) . . no O8 H8O 0.94(5) . . no O1 C6 1.220(3) . . yes O2 C12 1.226(3) . . yes N7 C16 1.372(4) . . yes N7 H7A 0.88(4) . . no N7 H7B 0.96(5) . . no N8 C23 1.372(4) . . yes N8 H8B 0.98(4) . . no N8 H8A 0.82(5) . . no N1 C5 1.345(4) . . yes N1 C1 1.333(4) . . yes N2 C6 1.332(4) . . yes N2 N3 1.417(4) . . yes N2 H2N 0.83(4) . . no N3 H3B 0.91(7) . . no N3 H3A 1.01(6) . . no N4 C11 1.340(4) . . yes N4 C7 1.333(4) . . yes N5 C12 1.328(4) . . yes N5 N6 1.420(3) . . yes N5 H5N 0.95(5) . . no N6 H6A 0.96(5) . . no N6 H6B 0.92(6) . . no C13 C14 1.402(4) . . no C13 C19 1.466(4) . . no C13 C18 1.407(4) . . no C14 C15 1.383(4) . . no C15 C16 1.402(4) . . no C16 C17 1.408(4) . . no C17 C18 1.376(4) . . no C15 H15 1.00(4) . . no C17 H17 0.94(3) . . no C18 H18 0.97(3) . . no C20 C26 1.472(4) . . no C20 C25 1.399(4) . . no C20 C21 1.405(4) . . no C21 C22 1.390(4) . . no C22 C23 1.389(4) . . no C23 C24 1.410(4) . . no C24 C25 1.370(4) . . no C22 H22 0.86(4) . . no C24 H24 0.91(4) . . no C25 H25 0.97(3) . . no C1 C2 1.382(4) . . no C2 C3 1.394(4) . . no C3 C4 1.388(4) . . no C3 C6 1.497(4) . . no C4 C5 1.376(5) . . no C1 H1 1.04(3) . . no C2 H2 0.92(4) . . no C4 H4 0.99(4) . . no C5 H5 0.96(4) . . no C7 C8 1.392(4) . . no C8 C9 1.383(4) . . no C9 C10 1.382(4) . . no C9 C12 1.511(4) . . no C10 C11 1.391(4) . . no C7 H7 0.86(3) . . no C8 H8 0.96(4) . . no C10 H10 0.99(4) . . no C11 H11 1.03(3) . . 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 C19 O4 H4O 117(3) . . . no C14 O5 H5O 103(3) . . . no C26 O7 H7O 113(3) . . . no C21 O8 H8O 95(3) . . . no C16 N7 H7A 119(2) . . . no H7A N7 H7B 113(4) . . . no C16 N7 H7B 118(3) . . . no C23 N8 H8B 118(2) . . . no C23 N8 H8A 123(3) . . . no H8A N8 H8B 116(4) . . . no C1 N1 C5 118.1(3) . . . yes N3 N2 C6 122.5(2) . . . yes N3 N2 H2N 111(3) . . . no C6 N2 H2N 127(3) . . . no H3A N3 H3B 103(6) . . . no N2 N3 H3A 107(4) . . . no N2 N3 H3B 104(4) . . . no C7 N4 C11 119.0(2) . . . yes N6 N5 C12 122.3(2) . . . yes C12 N5 H5N 125(3) . . . no N6 N5 H5N 113(3) . . . no N5 N6 H6B 108(3) . . . no N5 N6 H6A 111(3) . . . no H6A N6 H6B 110(5) . . . no C14 C13 C18 117.7(2) . . . no C18 C13 C19 121.3(2) . . . no C14 C13 C19 121.1(2) . . . no O5 C14 C15 118.0(2) . . . yes C13 C14 C15 121.1(2) . . . no O5 C14 C13 120.9(2) . . . yes C14 C15 C16 120.6(2) . . . no C15 C16 C17 118.8(2) . . . no N7 C16 C15 120.5(3) . . . yes N7 C16 C17 120.7(3) . . . yes C16 C17 C18 120.0(2) . . . no C13 C18 C17 121.8(2) . . . no O4 C19 C13 115.4(2) . . . yes O3 C19 C13 121.7(2) . . . yes O3 C19 O4 122.9(3) . . . yes C16 C15 H15 120.8(19) . . . no C14 C15 H15 118.6(19) . . . no C18 C17 H17 119.8(17) . . . no C16 C17 H17 120.1(17) . . . no C13 C18 H18 112.7(16) . . . no C17 C18 H18 125.3(16) . . . no C25 C20 C26 121.8(2) . . . no C21 C20 C26 120.2(2) . . . no C21 C20 C25 118.0(2) . . . no O8 C21 C22 118.8(2) . . . yes C20 C21 C22 120.2(3) . . . no O8 C21 C20 121.0(3) . . . yes C21 C22 C23 121.1(3) . . . no N8 C23 C22 121.7(3) . . . yes N8 C23 C24 119.5(3) . . . yes C22 C23 C24 118.8(3) . . . no C23 C24 C25 119.8(3) . . . no C20 C25 C24 122.0(2) . . . no O7 C26 C20 116.1(2) . . . yes O6 C26 O7 122.2(2) . . . yes O6 C26 C20 121.6(3) . . . yes C21 C22 H22 123(2) . . . no C23 C22 H22 116(2) . . . no C25 C24 H24 120(3) . . . no C23 C24 H24 120(3) . . . no C20 C25 H25 118.1(18) . . . no C24 C25 H25 119.7(18) . . . no N1 C1 C2 123.2(3) . . . yes C1 C2 C3 118.5(3) . . . no C2 C3 C6 123.5(2) . . . no C2 C3 C4 118.5(3) . . . no C4 C3 C6 118.0(2) . . . no C3 C4 C5 119.1(3) . . . no N1 C5 C4 122.6(3) . . . yes N2 C6 C3 116.4(2) . . . yes O1 C6 C3 121.3(2) . . . yes O1 C6 N2 122.3(3) . . . yes N1 C1 H1 106.1(18) . . . no C2 C1 H1 130.7(18) . . . no C3 C2 H2 121(2) . . . no C1 C2 H2 120(2) . . . no C3 C4 H4 118(2) . . . no C5 C4 H4 123(2) . . . no N1 C5 H5 114(2) . . . no C4 C5 H5 123(2) . . . no N4 C7 C8 122.8(3) . . . yes C7 C8 C9 118.2(3) . . . no C8 C9 C10 119.1(2) . . . no C10 C9 C12 118.4(2) . . . no C8 C9 C12 122.5(2) . . . no C9 C10 C11 119.4(2) . . . no N4 C11 C10 121.5(3) . . . yes O2 C12 C9 120.4(2) . . . yes N5 C12 C9 115.8(2) . . . yes O2 C12 N5 123.8(3) . . . yes N4 C7 H7 122(2) . . . no C8 C7 H7 115(2) . . . no C7 C8 H8 121(2) . . . no C9 C8 H8 121(2) . . . no C9 C10 H10 121(2) . . . no C11 C10 H10 119(2) . . . no N4 C11 H11 116.2(19) . . . no C10 C11 H11 122.3(19) . . . 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N1 C5 C4 0.4(5) . . . . no C5 N1 C1 C2 -0.9(5) . . . . no N3 N2 C6 C3 -178.9(4) . . . . no N3 N2 C6 O1 0.7(7) . . . . no C11 N4 C7 C8 -1.1(5) . . . . no C7 N4 C11 C10 0.7(5) . . . . no N6 N5 C12 C9 -177.7(3) . . . . no N6 N5 C12 O2 1.7(6) . . . . no C14 C13 C18 C17 -0.7(4) . . . . no C19 C13 C18 C17 178.7(3) . . . . no C19 C13 C14 O5 0.6(5) . . . . no C14 C13 C19 O4 170.1(3) . . . . no C18 C13 C19 O4 -9.2(5) . . . . no C14 C13 C19 O3 -8.3(5) . . . . no C18 C13 C14 O5 179.9(3) . . . . no C19 C13 C14 C15 -178.2(3) . . . . no C18 C13 C14 C15 1.1(4) . . . . no C18 C13 C19 O3 172.4(3) . . . . no C13 C14 C15 C16 0.0(4) . . . . no O5 C14 C15 C16 -178.9(3) . . . . no C14 C15 C16 C17 -1.6(4) . . . . no C14 C15 C16 N7 -179.4(3) . . . . no C15 C16 C17 C18 2.1(4) . . . . no N7 C16 C17 C18 179.8(3) . . . . no C16 C17 C18 C13 -1.0(4) . . . . no C26 C20 C21 C22 173.9(3) . . . . no C25 C20 C26 O7 -2.1(4) . . . . no C26 C20 C21 O8 -5.6(4) . . . . no C25 C20 C21 C22 -3.5(4) . . . . no C26 C20 C25 C24 -174.1(3) . . . . no C21 C20 C26 O6 -0.1(5) . . . . no C21 C20 C25 C24 3.2(4) . . . . no C25 C20 C26 O6 177.1(3) . . . . no C25 C20 C21 O8 177.1(3) . . . . no C21 C20 C26 O7 -179.4(3) . . . . no O8 C21 C22 C23 -179.8(3) . . . . no C20 C21 C22 C23 0.7(5) . . . . no C21 C22 C23 C24 2.4(5) . . . . no C21 C22 C23 N8 -179.2(3) . . . . no N8 C23 C24 C25 178.9(3) . . . . no C22 C23 C24 C25 -2.7(4) . . . . no C23 C24 C25 C20 -0.2(4) . . . . no N1 C1 C2 C3 0.7(5) . . . . no C1 C2 C3 C4 0.1(5) . . . . no C1 C2 C3 C6 179.5(3) . . . . no C4 C3 C6 O1 24.3(5) . . . . no C2 C3 C4 C5 -0.6(5) . . . . no C4 C3 C6 N2 -156.0(3) . . . . no C2 C3 C6 N2 24.6(5) . . . . no C6 C3 C4 C5 -180.0(3) . . . . no C2 C3 C6 O1 -155.1(4) . . . . no C3 C4 C5 N1 0.3(5) . . . . no N4 C7 C8 C9 0.4(5) . . . . no C7 C8 C9 C10 0.7(4) . . . . no C7 C8 C9 C12 178.9(3) . . . . no C8 C9 C12 N5 27.5(5) . . . . no C10 C9 C12 O2 26.3(5) . . . . no C10 C9 C12 N5 -154.3(3) . . . . no C8 C9 C12 O2 -151.9(4) . . . . no C8 C9 C10 C11 -1.0(4) . . . . no C12 C9 C10 C11 -179.3(3) . . . . no C9 C10 C11 N4 0.4(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 O1 C7 3.381(4) . 1_556 no O1 N3 2.752(4) . . no O1 O6 3.213(5) . 3_555 no O1 N6 3.022(5) . 3_555 no O2 O8 3.142(5) . 1_554 no O2 N6 2.777(4) . . no O2 N3 3.057(5) . 3_544 no O3 O5 2.590(3) . . no O3 C1 3.331(4) . 2_654 no O3 N8 3.077(4) . 3_544 no O4 N1 2.581(3) . 2_654 no O4 C1 3.398(4) . 2_654 no O5 O3 2.590(3) . . no O5 N5 3.052(4) . . no O6 O1 3.213(5) . 3_544 no O6 N7 3.023(4) . 3_545 no O6 O8 2.564(3) . . no O7 N4 2.566(3) . 3_545 no O8 N2 3.037(4) . 4_455 no O8 O6 2.564(3) . . no O8 O2 3.142(5) . 1_556 no O1 H4 2.53(3) . . no O1 H3A 2.60(7) . . no O1 H7 2.52(3) . 1_556 no O1 H6A 2.12(5) . 3_555 no O1 H3B 2.66(7) . . no O2 H6B 2.81(6) . . no O2 H10 2.62(3) . . no O2 H6A 2.72(5) . . no O2 H2 2.92(4) . 4_454 no O2 H3A 2.13(6) . 3_544 no O3 H1 2.56(3) . 2_654 no O3 H5O 1.73(4) . . no O3 H8A 2.31(5) . 3_544 no O4 H18 2.36(3) . . no O4 H11 2.63(3) . 4_555 no O5 H25 2.79(3) . . no O5 H5N 2.13(5) . . no O6 H7B 2.16(5) . 3_545 no O6 H8O 1.64(5) . . no O6 H6B 2.51(7) . 1_556 no O7 H25 2.45(3) . . no O7 H5 2.69(4) . . no O8 H2N 2.25(5) . 4_455 no O8 H3B 2.68(7) . 3_544 no N1 O4 2.581(3) . 2_655 no N1 C19 3.327(4) . 2_655 no N2 O8 3.037(4) . 4_555 no N3 O2 3.057(5) . 3_555 no N3 O1 2.752(4) . . no N3 N7 3.120(4) . 2_665 no N4 C26 3.319(4) . 3_554 no N4 O7 2.566(3) . 3_554 no N5 O5 3.052(4) . . no N6 O1 3.022(5) . 3_544 no N6 O2 2.777(4) . . no N6 N8 3.176(4) . 3_544 no N7 O6 3.023(4) . 3_554 no N7 N3 3.120(4) . 2_664 no N8 C11 3.327(5) . . no N8 O3 3.077(4) . 3_555 no N8 N6 3.176(4) . 3_555 no N1 H4O 1.56(5) . 2_655 no N2 H2 2.67(3) . . no N3 H7A 2.25(4) . 2_665 no N4 H7O 1.56(5) . 3_554 no N5 H8 2.66(4) . . no N6 H8B 2.21(4) . 3_544 no C1 O3 3.331(4) . 2_655 no C1 C18 3.591(5) . 1_556 no C1 O4 3.398(4) . 2_655 no C1 C13 3.355(5) . 1_556 no C2 C17 3.576(5) . 1_556 no C3 C15 3.459(4) . 1_556 no C3 C16 3.574(4) . 1_556 no C3 C17 3.458(4) . . no C4 C17 3.559(5) . . no C4 C25 3.587(4) . . no C5 C18 3.596(5) . . no C5 C13 3.464(5) . . no C7 O1 3.381(4) . 1_554 no C7 C23 3.442(5) . 1_554 no C7 C24 3.558(5) . 1_554 no C8 C24 3.518(4) . 1_554 no C8 C25 3.575(4) . 1_554 no C8 C23 3.514(4) . 1_554 no C9 C21 3.557(4) . 1_554 no C9 C22 3.582(5) . 1_554 no C10 C23 3.382(4) . . no C10 C22 3.472(5) . . no C11 N8 3.327(5) . . no C11 C23 3.381(5) . . no C12 C21 3.524(5) . 1_554 no C13 C5 3.464(5) . . no C13 C1 3.355(5) . 1_554 no C15 C25 3.554(4) . . no C15 C3 3.459(4) . 1_554 no C16 C3 3.574(4) . 1_554 no C17 C2 3.576(5) . 1_554 no C17 C4 3.559(5) . . no C17 C3 3.458(4) . . no C18 C1 3.591(5) . 1_554 no C18 C5 3.596(5) . . no C19 N1 3.327(4) . 2_654 no C21 C9 3.557(4) . 1_556 no C21 C12 3.524(5) . 1_556 no C22 C9 3.582(5) . 1_556 no C22 C10 3.472(5) . . no C23 C11 3.381(5) . . no C23 C7 3.442(5) . 1_556 no C23 C8 3.514(4) . 1_556 no C23 C10 3.382(4) . . no C24 C7 3.558(5) . 1_556 no C24 C8 3.518(4) . 1_556 no C25 C8 3.575(4) . 1_556 no C25 C4 3.587(4) . . no C25 C15 3.554(4) . . no C26 N4 3.319(4) . 3_545 no C1 H22 2.95(4) . 4_555 no C1 H4O 2.51(5) . 2_655 no C2 H22 2.91(4) . 4_555 no C2 H2N 2.70(5) . . no C4 H25 3.00(3) . . no C5 H4O 2.55(5) . 2_655 no C7 H7O 2.49(5) . 3_554 no C7 H15 2.76(4) . . no C8 H5N 2.64(5) . . no C8 H15 2.71(4) . . no C10 H2 3.04(4) . 4_454 no C11 H1 2.93(3) . 4_454 no C11 H7O 2.54(5) . 3_554 no C14 H25 2.87(3) . . no C15 H25 2.89(3) . . no C17 H10 2.95(4) . 4_555 no C18 H10 2.74(4) . 4_555 no C19 H5O 2.27(4) . . no C22 H18 2.98(3) . 4_455 no C24 H4 2.95(4) . . no C25 H8 3.08(4) . 1_556 no C25 H4 2.80(4) . . no C26 H8O 2.14(5) . . no H1 H4O 2.42(6) . 2_655 no H1 C11 2.93(3) . 4_556 no H1 O3 2.56(3) . 2_655 no H2 C10 3.04(4) . 4_556 no H2 O2 2.92(4) . 4_556 no H2 H2N 2.27(6) . . no H2 N2 2.67(3) . . no H2N O8 2.25(5) . 4_555 no H2N H2 2.27(6) . . no H2N C2 2.70(5) . . no H3A O2 2.13(6) . 3_555 no H3A O1 2.60(7) . . no H3B O1 2.66(7) . . no H3B O8 2.68(7) . 3_555 no H4 H25 2.38(5) . . no H4 O1 2.53(3) . . no H4 C25 2.80(4) . . no H4 C24 2.95(4) . . no H4O C5 2.55(5) . 2_654 no H4O C1 2.51(5) . 2_654 no H4O H1 2.42(6) . 2_654 no H4O N1 1.56(5) . 2_654 no H5 O7 2.69(4) . . no H5N O5 2.13(5) . . no H5N H5O 2.57(6) . . no H5N H8 2.23(6) . . no H5N C8 2.64(5) . . no H5O O3 1.73(4) . . no H5O C19 2.27(4) . . no H5O H5N 2.57(6) . . no H6A O2 2.72(5) . . no H6A O1 2.12(5) . 3_544 no H6B O2 2.81(6) . . no H6B H8B 2.50(7) . 3_544 no H6B O6 2.51(7) . 1_554 no H7 O1 2.52(3) . 1_554 no H7A N3 2.25(4) . 2_664 no H7A H17 2.44(5) . . no H7B H15 2.45(6) . . no H7B O6 2.16(5) . 3_554 no H7O C11 2.54(5) . 3_545 no H7O C7 2.49(5) . 3_545 no H7O N4 1.56(5) . 3_545 no H8 H5N 2.23(6) . . no H8 N5 2.66(4) . . no H8 C25 3.08(4) . 1_554 no H8A H22 2.43(6) . . no H8A O3 2.31(5) . 3_555 no H8B H24 2.37(6) . . no H8B N6 2.21(4) . 3_555 no H8B H6B 2.50(7) . 3_555 no H8O O6 1.64(5) . . no H8O C26 2.14(5) . . no H10 C17 2.95(4) . 4_455 no H10 H18 2.47(4) . 4_455 no H10 C18 2.74(4) . 4_455 no H10 O2 2.62(3) . . no H11 O4 2.63(3) . 4_455 no H15 C7 2.76(4) . . no H15 H7B 2.45(6) . . no H15 C8 2.71(4) . . no H17 H7A 2.44(5) . . no H18 H10 2.47(4) . 4_555 no H18 H22 2.45(5) . 4_555 no H18 O4 2.36(3) . . no H18 C22 2.98(3) . 4_555 no H22 H8A 2.43(6) . . no H22 C2 2.91(4) . 4_455 no H22 H18 2.45(5) . 4_455 no H22 C1 2.95(4) . 4_455 no H24 H8B 2.37(6) . . no H25 O7 2.45(3) . . no H25 C4 3.00(3) . . no H25 O5 2.79(3) . . no H25 C15 2.89(3) . . no H25 H4 2.38(5) . . no H25 C14 2.87(3) . . no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # N2 H2N O8 0.83(4) 2.25(5) 3.037(4) 159(5) 4_555 yes N3 H3A O2 1.01(6) 2.13(6) 3.057(5) 151(5) 3_555 yes O4 H4O N1 1.02(5) 1.56(5) 2.581(3) 173(4) 2_654 yes N5 H5N O5 0.95(5) 2.13(5) 3.052(4) 165(5) . yes O5 H5O O3 0.92(4) 1.73(4) 2.590(3) 154(4) . yes N6 H6A O1 0.96(5) 2.12(5) 3.022(5) 157(5) 3_544 yes N6 H6B O6 0.92(6) 2.51(7) 3.335(6) 149(4) 1_554 yes N7 H7A N3 0.88(4) 2.25(4) 3.120(4) 169(3) 2_664 yes N7 H7B O6 0.96(5) 2.16(5) 3.023(4) 149(4) 3_554 yes O7 H7O N4 1.01(5) 1.56(5) 2.566(3) 177(9) 3_545 yes N8 H8A O3 0.82(5) 2.31(5) 3.077(4) 157(4) 3_555 yes N8 H8B N6 0.98(4) 2.21(4) 3.176(4) 168(3) 3_555 yes O8 H8O O6 0.94(5) 1.64(5) 2.564(3) 167(5) . yes C1 H1 O3 1.04(3) 2.56(3) 3.331(4) 130(3) 2_655 yes C7 H7 O1 0.86(3) 2.52(3) 3.381(4) 178(4) 1_554 yes C18 H18 O4 0.97(3) 2.36(3) 2.763(4) 104.4(19) . yes #===END # Attachment 'web_deposit_cif_file_8_PawelGrobelny_1289286463.cif' # CIF-file generated for datam in Pna2(1) #=============================================================================== data_datam9 _database_code_depnum_ccdc_archive 'CCDC 800238' #TrackingRef 'web_deposit_cif_file_8_PawelGrobelny_1289286463.cif' #=============================================================================== _chemical_name_systematic ; ; _chemical_name_common 'Isoniazid:4-aminosalicylic acid co-crystal' _chemical_melting_point ? _chemical_formula_moiety 'C7 H7 N O3, C6 H7 N3 O' _chemical_formula_sum 'C13 H14 N4 O4' _chemical_formula_iupac ? _chemical_formula_weight 290.28 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_space_group_name_H-M 'P n a 21' _symmetry_Int_Tables_number 33 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,1/2+z 3 1/2-x,1/2+y,1/2+z 4 1/2+x,1/2-y,z _cell_length_a 21.969(2) _cell_length_b 16.485(2) _cell_length_c 7.3209(9) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2651.3(5) _cell_formula_units_Z 8 _cell_measurement_temperature 260(2) _cell_measurement_reflns_used 6500 _cell_measurement_theta_min 1.5 _cell_measurement_theta_max 27.5 _cell_special_details ; ; _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.454 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 0.111 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.9571 _exptl_absorpt_correction_T_max 0.9836 #=============================================================================== _exptl_special_details ; ; _diffrn_ambient_temperature 260(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_source_power 0.6 _diffrn_source_voltage 50.0 _diffrn_source_current 12.0 _diffrn_radiation_wavelength 0.71075 _diffrn_source 'Sealed Tube' _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_measurement_specimen_support Fiber _diffrn_detector CCD _diffrn_measurement_device ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_detector_area_resol_mean 13.6612 _diffrn_measurement_method 'profile data from \w-scans' _diffrn_reflns_number 27415 _diffrn_reflns_av_R_equivalents 0.0535 _diffrn_reflns_av_sigmaI/netI 0.0278 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 27.54 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.995 _reflns_number_total 3286 _reflns_number_gt 2989 _reflns_threshold_expression >2sigma(I) _diffrn_measurement_details ; scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 0.0000 XTD: 49.4072 2theta: 29.5726 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 120.0000 XTD: 49.4072 2theta: 29.5726 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 240.0000 XTD: 49.4072 2theta: 29.5726 ; _diffrn_orient_matrix_UB_11 0.015155 _diffrn_orient_matrix_UB_12 -0.134733 _diffrn_orient_matrix_UB_13 0.016601 _diffrn_orient_matrix_UB_21 0.060214 _diffrn_orient_matrix_UB_22 0.007038 _diffrn_orient_matrix_UB_23 0.002155 _diffrn_orient_matrix_UB_31 -0.002237 _diffrn_orient_matrix_UB_32 0.005312 _diffrn_orient_matrix_UB_33 0.045152 _diffrn_orient_matrix_type d*Trek _diffrn_reflns_reduction_process ; ; _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== _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^)+(0.0732P)^2^+0.2260P] 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 3286 _refine_ls_number_parameters 492 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0511 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.1305 _refine_ls_wR_factor_gt 0.1178 _refine_ls_goodness_of_fit_ref 1.162 _refine_ls_restrained_S_all 1.162 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.185 _refine_diff_density_min -0.172 _refine_diff_density_rms 0.057 #=============================================================================== loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags O3 O Uani 0.42373(10) 0.00433(12) 0.1155(4) 1.000 0.0583(8) . . O4 O Uani 0.52037(9) 0.03813(13) 0.1728(5) 1.000 0.0554(8) . . O5 O Uani 0.34682(9) 0.11843(14) 0.0385(4) 1.000 0.0500(7) . . N7 N Uani 0.40848(14) 0.39126(16) 0.1424(5) 1.000 0.0553(10) . . C13 C Uani 0.44844(12) 0.14295(16) 0.1488(4) 1.000 0.0367(8) . . C14 C Uani 0.39113(12) 0.17111(17) 0.0938(4) 1.000 0.0367(8) . . C15 C Uani 0.37820(12) 0.25296(17) 0.0919(4) 1.000 0.0381(8) . . C16 C Uani 0.42200(13) 0.30986(16) 0.1434(4) 1.000 0.0390(8) . . C17 C Uani 0.47922(13) 0.28223(17) 0.2032(4) 1.000 0.0392(8) . . C18 C Uani 0.49180(12) 0.20048(17) 0.2037(4) 1.000 0.0361(8) . . C19 C Uani 0.46281(12) 0.05627(17) 0.1455(5) 1.000 0.0425(8) . . O6 O Uani 0.18284(10) 0.00820(13) 0.4810(4) 1.000 0.0575(8) . . O7 O Uani 0.27796(9) 0.03910(12) 0.4007(4) 1.000 0.0551(8) . . O8 O Uani 0.10164(9) 0.11947(16) 0.4901(4) 1.000 0.0546(8) . . N8 N Uani 0.16826(14) 0.39344(16) 0.4204(5) 1.000 0.0544(10) . . C20 C Uani 0.20710(11) 0.14529(15) 0.4180(4) 1.000 0.0355(7) . . C21 C Uani 0.14764(12) 0.17296(18) 0.4537(4) 1.000 0.0390(8) . . C22 C Uani 0.13487(13) 0.2549(2) 0.4549(5) 1.000 0.0427(9) . . C23 C Uani 0.17985(13) 0.31188(16) 0.4175(4) 1.000 0.0400(8) . . C24 C Uani 0.23897(13) 0.28423(18) 0.3724(4) 1.000 0.0401(9) . . C25 C Uani 0.25123(13) 0.20288(17) 0.3729(4) 1.000 0.0391(9) . . C26 C Uani 0.22196(13) 0.05893(17) 0.4342(4) 1.000 0.0415(9) . . O1 O Uani 0.37657(9) 0.39768(13) 0.6645(4) 1.000 0.0580(8) . . N1 N Uani 0.45701(11) 0.11548(15) 0.6605(4) 1.000 0.0444(8) . . N2 N Uani 0.47722(12) 0.41917(15) 0.6504(5) 1.000 0.0553(9) . . N3 N Uani 0.47262(14) 0.50459(17) 0.6500(8) 1.000 0.0665(12) . . C1 C Uani 0.50103(13) 0.16492(18) 0.7203(5) 1.000 0.0440(9) . . C2 C Uani 0.49493(13) 0.24801(18) 0.7230(5) 1.000 0.0396(9) . . C3 C Uani 0.44044(11) 0.28194(16) 0.6623(4) 1.000 0.0358(8) . . C4 C Uani 0.39467(13) 0.2307(2) 0.6026(4) 1.000 0.0417(8) . . C5 C Uani 0.40464(13) 0.14794(19) 0.6040(5) 1.000 0.0456(9) . . C6 C Uani 0.42842(12) 0.37104(17) 0.6586(5) 1.000 0.0413(9) . . O2 O Uani 0.11418(10) 0.10679(13) 0.9169(5) 1.000 0.0585(8) . . N4 N Uani 0.20131(11) 0.38584(14) 0.9096(4) 1.000 0.0417(7) . . N5 N Uani 0.21486(12) 0.08207(14) 0.9317(4) 1.000 0.0460(8) . . N6 N Uani 0.20935(15) -0.00360(16) 0.9302(6) 1.000 0.0567(10) . . C7 C Uani 0.24291(13) 0.33427(18) 0.8459(5) 1.000 0.0417(9) . . C8 C Uani 0.23465(13) 0.25078(18) 0.8478(4) 1.000 0.0383(9) . . C9 C Uani 0.18097(12) 0.22032(15) 0.9180(4) 1.000 0.0347(7) . . C10 C Uani 0.13715(12) 0.27373(18) 0.9816(4) 1.000 0.0383(8) . . C11 C Uani 0.14899(12) 0.35617(18) 0.9763(5) 1.000 0.0427(9) . . C12 C Uani 0.16693(12) 0.13070(16) 0.9231(5) 1.000 0.0390(8) . . H4O H Uiso 0.528(2) -0.023(3) 0.153(8) 1.000 0.078(13) . . H5O H Uiso 0.366(2) 0.069(3) 0.054(8) 1.000 0.084(14) . . H7A H Uiso 0.4362(16) 0.426(2) 0.141(6) 1.000 0.054(10) . . H7B H Uiso 0.368(3) 0.412(5) 0.073(15) 1.000 0.19(4) . . H15 H Uiso 0.3362(17) 0.269(2) 0.060(6) 1.000 0.056(10) . . H17 H Uiso 0.5090(15) 0.3207(19) 0.233(5) 1.000 0.042(9) . . H18 H Uiso 0.5281(13) 0.1744(17) 0.254(4) 1.000 0.029(7) . . H7O H Uiso 0.287(3) -0.022(4) 0.400(12) 1.000 0.16(3) . . H8A H Uiso 0.1330(18) 0.407(2) 0.474(6) 1.000 0.055(11) . . H8B H Uiso 0.2030(18) 0.434(2) 0.404(6) 1.000 0.059(11) . . H8O H Uiso 0.123(2) 0.070(3) 0.489(8) 1.000 0.090(16) . . H22 H Uiso 0.0996(16) 0.275(2) 0.484(5) 1.000 0.051(10) . . H24 H Uiso 0.2706(17) 0.320(2) 0.357(6) 1.000 0.056(11) . . H25 H Uiso 0.2912(16) 0.1855(19) 0.351(5) 1.000 0.046(9) . . H1 H Uiso 0.5378(16) 0.126(2) 0.760(6) 1.000 0.060(11) . . H2 H Uiso 0.5275(16) 0.282(2) 0.764(5) 1.000 0.053(10) . . H2N H Uiso 0.5134(19) 0.400(2) 0.639(7) 1.000 0.075(13) . . H3A H Uiso 0.452(3) 0.516(3) 0.760(8) 1.000 0.087(17) . . H3B H Uiso 0.443(3) 0.519(4) 0.560(9) 1.000 0.11(2) . . H4 H Uiso 0.3567(16) 0.252(2) 0.570(6) 1.000 0.053(10) . . H5 H Uiso 0.3743(17) 0.108(2) 0.562(6) 1.000 0.057(10) . . H5N H Uiso 0.254(2) 0.098(2) 0.949(7) 1.000 0.074(13) . . H6A H Uiso 0.184(2) -0.020(3) 1.030(7) 1.000 0.068(13) . . H6B H Uiso 0.196(3) -0.023(4) 0.830(11) 1.000 0.12(2) . . H7 H Uiso 0.2769(13) 0.3524(16) 0.802(4) 1.000 0.026(7) . . H8 H Uiso 0.2614(19) 0.220(3) 0.806(7) 1.000 0.070(13) . . H10 H Uiso 0.1002(16) 0.254(2) 1.040(5) 1.000 0.049(10) . . H11 H Uiso 0.1179(15) 0.3979(19) 1.026(5) 1.000 0.042(8) . . 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 O3 0.0386(10) 0.0373(10) 0.099(2) -0.0074(12) -0.0047(12) -0.0061(8) O4 0.0351(10) 0.0383(10) 0.0928(19) 0.0011(13) -0.0045(12) 0.0009(8) O5 0.0315(10) 0.0456(11) 0.0729(15) -0.0032(11) -0.0088(10) -0.0066(8) N7 0.0508(16) 0.0350(13) 0.080(2) 0.0008(14) -0.0074(16) 0.0001(12) C13 0.0307(12) 0.0366(13) 0.0429(14) -0.0022(13) 0.0016(11) -0.0030(10) C14 0.0281(12) 0.0419(14) 0.0401(14) -0.0014(12) 0.0023(11) -0.0065(10) C15 0.0283(12) 0.0427(15) 0.0432(16) 0.0027(12) -0.0012(11) -0.0012(10) C16 0.0399(14) 0.0373(13) 0.0398(14) -0.0003(12) 0.0023(12) -0.0011(10) C17 0.0357(13) 0.0373(14) 0.0446(16) -0.0036(13) -0.0040(12) -0.0060(11) C18 0.0288(12) 0.0399(13) 0.0397(15) -0.0011(12) -0.0034(11) -0.0009(10) C19 0.0362(13) 0.0398(14) 0.0516(16) -0.0012(14) -0.0003(13) -0.0025(11) O6 0.0458(12) 0.0388(11) 0.0880(19) -0.0001(12) 0.0079(13) -0.0104(9) O7 0.0421(11) 0.0325(10) 0.0907(18) 0.0034(12) 0.0114(13) 0.0025(8) O8 0.0297(10) 0.0571(13) 0.0771(17) 0.0072(13) 0.0035(10) -0.0066(9) N8 0.0532(17) 0.0397(13) 0.0703(19) -0.0025(15) 0.0032(16) 0.0132(12) C20 0.0289(12) 0.0362(13) 0.0413(13) -0.0012(12) 0.0001(11) 0.0002(10) C21 0.0288(12) 0.0471(15) 0.0411(15) 0.0018(13) -0.0016(11) -0.0031(11) C22 0.0301(13) 0.0523(18) 0.0456(16) 0.0008(14) 0.0005(12) 0.0110(12) C23 0.0403(14) 0.0400(14) 0.0397(14) -0.0015(13) -0.0013(13) 0.0098(11) C24 0.0338(14) 0.0368(15) 0.0497(18) -0.0010(14) 0.0020(13) 0.0010(11) C25 0.0307(13) 0.0381(14) 0.0485(17) -0.0027(12) 0.0033(12) -0.0006(10) C26 0.0362(14) 0.0364(14) 0.0518(17) -0.0027(13) 0.0009(13) -0.0040(11) O1 0.0333(10) 0.0477(12) 0.093(2) 0.0096(13) 0.0096(13) 0.0066(8) N1 0.0386(12) 0.0400(12) 0.0545(15) 0.0016(13) 0.0015(11) -0.0010(10) N2 0.0348(12) 0.0351(12) 0.096(2) 0.0022(16) 0.0073(16) 0.0023(10) N3 0.0477(15) 0.0358(14) 0.116(3) 0.0034(19) 0.008(2) -0.0009(11) C1 0.0362(14) 0.0435(15) 0.0524(18) 0.0053(14) -0.0021(13) 0.0024(12) C2 0.0325(13) 0.0421(16) 0.0443(17) 0.0012(13) -0.0034(12) -0.0035(11) C3 0.0290(12) 0.0410(14) 0.0374(13) 0.0025(12) 0.0035(11) 0.0004(10) C4 0.0302(12) 0.0480(15) 0.0469(15) 0.0018(14) 0.0006(12) 0.0024(11) C5 0.0345(14) 0.0453(15) 0.0569(18) -0.0031(15) -0.0004(13) -0.0040(12) C6 0.0334(13) 0.0396(14) 0.0508(17) 0.0028(14) 0.0068(12) 0.0028(11) O2 0.0352(11) 0.0443(12) 0.0960(19) 0.0046(14) -0.0043(13) -0.0106(9) N4 0.0403(13) 0.0318(11) 0.0531(14) 0.0022(12) -0.0071(12) -0.0048(9) N5 0.0374(13) 0.0300(11) 0.0706(18) -0.0012(13) -0.0069(13) -0.0043(9) N6 0.0569(17) 0.0281(12) 0.085(2) 0.0013(15) -0.0031(19) -0.0032(10) C7 0.0329(14) 0.0385(14) 0.0537(17) 0.0038(13) 0.0019(12) -0.0043(11) C8 0.0342(14) 0.0394(17) 0.0412(17) 0.0005(12) -0.0005(11) -0.0013(11) C9 0.0324(12) 0.0321(12) 0.0395(13) 0.0004(12) -0.0043(11) -0.0031(9) C10 0.0281(12) 0.0383(14) 0.0486(16) -0.0010(12) -0.0010(12) -0.0034(10) C11 0.0339(13) 0.0404(14) 0.0538(17) -0.0030(13) -0.0037(13) 0.0032(11) C12 0.0370(14) 0.0353(13) 0.0447(15) 0.0006(13) -0.0038(12) -0.0043(10) #=============================================================================== _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; 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 O3 C19 1.232(3) . . yes O4 C19 1.315(3) . . yes O5 C14 1.366(4) . . yes O4 H4O 1.03(5) . . no O5 H5O 0.92(5) . . no O6 C26 1.247(4) . . yes O7 C26 1.296(4) . . yes O8 C21 1.367(4) . . yes O7 H7O 1.03(7) . . no O8 H8O 0.94(5) . . no O1 C6 1.222(3) . . yes O2 C12 1.225(3) . . yes N7 C16 1.374(4) . . yes N7 H7A 0.84(3) . . no N7 H7B 1.08(8) . . no N8 C23 1.369(4) . . yes N8 H8B 1.02(4) . . no N8 H8A 0.90(4) . . no N1 C5 1.335(4) . . yes N1 C1 1.338(4) . . yes N2 C6 1.335(4) . . yes N2 N3 1.412(4) . . yes N2 H2N 0.86(4) . . no N3 H3B 0.96(6) . . no N3 H3A 0.94(6) . . no N4 C11 1.341(4) . . yes N4 C7 1.333(4) . . yes N5 C12 1.325(4) . . yes N5 N6 1.418(4) . . yes N5 H5N 0.91(4) . . no N6 H6A 0.96(5) . . no N6 H6B 0.85(7) . . no C13 C14 1.401(4) . . no C13 C19 1.464(4) . . no C13 C18 1.403(4) . . no C14 C15 1.379(4) . . no C15 C16 1.396(4) . . no C16 C17 1.407(4) . . no C17 C18 1.376(4) . . no C15 H15 0.99(4) . . no C17 H17 0.94(3) . . no C18 H18 0.98(3) . . no C20 C26 1.465(4) . . no C20 C25 1.397(4) . . no C20 C21 1.408(4) . . no C21 C22 1.380(4) . . no C22 C23 1.391(4) . . no C23 C24 1.416(4) . . no C24 C25 1.368(4) . . no C22 H22 0.87(4) . . no C24 H24 0.92(4) . . no C25 H25 0.94(3) . . no C1 C2 1.376(4) . . no C2 C3 1.394(4) . . no C3 C4 1.384(4) . . no C3 C6 1.493(4) . . no C4 C5 1.382(5) . . no C1 H1 1.07(4) . . no C2 H2 0.96(4) . . no C4 H4 0.94(4) . . no C5 H5 0.99(4) . . no C7 C8 1.388(4) . . no C8 C9 1.381(4) . . no C9 C10 1.385(4) . . no C9 C12 1.510(4) . . no C10 C11 1.384(4) . . no C7 H7 0.87(3) . . no C8 H8 0.84(5) . . no C10 H10 0.97(4) . . no C11 H11 1.04(3) . . 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 C19 O4 H4O 111(2) . . . no C14 O5 H5O 102(3) . . . no C26 O7 H7O 116(4) . . . no C21 O8 H8O 101(3) . . . no C16 N7 H7A 121(2) . . . no H7A N7 H7B 112(5) . . . no C16 N7 H7B 119(4) . . . no C23 N8 H8B 120(2) . . . no C23 N8 H8A 114(2) . . . no H8A N8 H8B 122(3) . . . no C1 N1 C5 118.7(3) . . . yes N3 N2 C6 122.4(3) . . . yes N3 N2 H2N 116(2) . . . no C6 N2 H2N 122(2) . . . no H3A N3 H3B 102(6) . . . no N2 N3 H3A 103(3) . . . no N2 N3 H3B 107(4) . . . no C7 N4 C11 118.9(2) . . . yes N6 N5 C12 122.3(3) . . . yes C12 N5 H5N 126(2) . . . no N6 N5 H5N 112(2) . . . no N5 N6 H6B 114(5) . . . no N5 N6 H6A 109(3) . . . no H6A N6 H6B 111(6) . . . no C14 C13 C18 117.9(2) . . . no C18 C13 C19 121.2(2) . . . no C14 C13 C19 120.8(2) . . . no O5 C14 C15 118.2(2) . . . yes C13 C14 C15 120.8(2) . . . no O5 C14 C13 121.0(2) . . . yes C14 C15 C16 120.9(2) . . . no C15 C16 C17 118.9(2) . . . no N7 C16 C15 120.4(3) . . . yes N7 C16 C17 120.7(3) . . . yes C16 C17 C18 119.8(3) . . . no C13 C18 C17 121.7(3) . . . no O4 C19 C13 115.3(2) . . . yes O3 C19 C13 122.1(2) . . . yes O3 C19 O4 122.6(3) . . . yes C16 C15 H15 122(2) . . . no C14 C15 H15 117.2(19) . . . no C18 C17 H17 121.5(19) . . . no C16 C17 H17 118.5(19) . . . no C13 C18 H18 111.4(17) . . . no C17 C18 H18 126.6(17) . . . no C25 C20 C26 121.7(2) . . . no C21 C20 C26 120.4(2) . . . no C21 C20 C25 117.9(2) . . . no O8 C21 C22 118.7(2) . . . yes C20 C21 C22 120.5(3) . . . no O8 C21 C20 120.9(3) . . . yes C21 C22 C23 121.0(3) . . . no N8 C23 C22 121.9(3) . . . yes N8 C23 C24 119.4(3) . . . yes C22 C23 C24 118.7(3) . . . no C23 C24 C25 119.7(3) . . . no C20 C25 C24 122.0(3) . . . no O7 C26 C20 116.2(2) . . . yes O6 C26 O7 122.5(3) . . . yes O6 C26 C20 121.3(3) . . . yes C21 C22 H22 124(2) . . . no C23 C22 H22 115(2) . . . no C25 C24 H24 119(2) . . . no C23 C24 H24 121(2) . . . no C20 C25 H25 119(2) . . . no C24 C25 H25 119(2) . . . no N1 C1 C2 122.7(3) . . . yes C1 C2 C3 118.6(3) . . . no C2 C3 C6 123.5(2) . . . no C2 C3 C4 118.7(3) . . . no C4 C3 C6 117.8(2) . . . no C3 C4 C5 119.0(3) . . . no N1 C5 C4 122.3(3) . . . yes N2 C6 C3 116.3(2) . . . yes O1 C6 C3 121.2(2) . . . yes O1 C6 N2 122.5(3) . . . yes N1 C1 H1 105.6(19) . . . no C2 C1 H1 131.7(19) . . . no C3 C2 H2 121(2) . . . no C1 C2 H2 121(2) . . . no C3 C4 H4 120(2) . . . no C5 C4 H4 121(2) . . . no N1 C5 H5 114(2) . . . no C4 C5 H5 123(2) . . . no N4 C7 C8 122.6(3) . . . yes C7 C8 C9 118.4(3) . . . no C8 C9 C10 119.2(2) . . . no C10 C9 C12 118.2(2) . . . no C8 C9 C12 122.7(2) . . . no C9 C10 C11 119.0(2) . . . no N4 C11 C10 122.0(3) . . . yes O2 C12 C9 120.5(2) . . . yes N5 C12 C9 115.5(2) . . . yes O2 C12 N5 124.0(3) . . . yes N4 C7 H7 120.1(18) . . . no C8 C7 H7 117.3(18) . . . no C7 C8 H8 121(3) . . . no C9 C8 H8 121(3) . . . no C9 C10 H10 121(2) . . . no C11 C10 H10 120(2) . . . no N4 C11 H11 116.8(18) . . . no C10 C11 H11 121.2(18) . . . 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N1 C5 C4 1.0(5) . . . . no C5 N1 C1 C2 -1.2(5) . . . . no N3 N2 C6 C3 -178.6(4) . . . . no N3 N2 C6 O1 0.7(6) . . . . no C11 N4 C7 C8 -0.8(5) . . . . no C7 N4 C11 C10 0.3(5) . . . . no N6 N5 C12 C9 -177.5(3) . . . . no N6 N5 C12 O2 1.5(6) . . . . no C14 C13 C18 C17 -0.4(4) . . . . no C19 C13 C18 C17 178.5(3) . . . . no C19 C13 C14 O5 1.1(4) . . . . no C14 C13 C19 O4 170.0(3) . . . . no C18 C13 C19 O4 -8.8(5) . . . . no C14 C13 C19 O3 -8.6(5) . . . . no C18 C13 C14 O5 179.9(3) . . . . no C19 C13 C14 C15 -178.1(3) . . . . no C18 C13 C14 C15 0.7(4) . . . . no C18 C13 C19 O3 172.6(3) . . . . no C13 C14 C15 C16 0.5(4) . . . . no O5 C14 C15 C16 -178.7(3) . . . . no C14 C15 C16 C17 -2.0(4) . . . . no C14 C15 C16 N7 -179.5(3) . . . . no C15 C16 C17 C18 2.4(4) . . . . no N7 C16 C17 C18 179.8(3) . . . . no C16 C17 C18 C13 -1.2(4) . . . . no C26 C20 C21 C22 174.0(3) . . . . no C25 C20 C26 O7 -1.4(4) . . . . no C26 C20 C21 O8 -5.1(4) . . . . no C25 C20 C21 C22 -4.0(4) . . . . no C26 C20 C25 C24 -174.4(3) . . . . no C21 C20 C26 O6 -0.6(5) . . . . no C21 C20 C25 C24 3.6(4) . . . . no C25 C20 C26 O6 177.4(3) . . . . no C25 C20 C21 O8 176.9(3) . . . . no C21 C20 C26 O7 -179.3(3) . . . . no O8 C21 C22 C23 -179.5(3) . . . . no C20 C21 C22 C23 1.3(5) . . . . no C21 C22 C23 C24 1.9(5) . . . . no C21 C22 C23 N8 -179.1(3) . . . . no N8 C23 C24 C25 178.7(3) . . . . no C22 C23 C24 C25 -2.3(4) . . . . no C23 C24 C25 C20 -0.4(4) . . . . no N1 C1 C2 C3 0.5(5) . . . . no C1 C2 C3 C4 0.3(5) . . . . no C1 C2 C3 C6 -180.0(3) . . . . no C4 C3 C6 O1 24.5(5) . . . . no C2 C3 C4 C5 -0.4(4) . . . . no C4 C3 C6 N2 -156.1(3) . . . . no C2 C3 C6 N2 24.1(5) . . . . no C6 C3 C4 C5 179.8(3) . . . . no C2 C3 C6 O1 -155.3(3) . . . . no C3 C4 C5 N1 -0.2(5) . . . . no N4 C7 C8 C9 0.3(5) . . . . no C7 C8 C9 C10 0.8(4) . . . . no C7 C8 C9 C12 178.8(3) . . . . no C8 C9 C12 N5 27.6(5) . . . . no C10 C9 C12 O2 26.5(5) . . . . no C10 C9 C12 N5 -154.4(3) . . . . no C8 C9 C12 O2 -151.5(4) . . . . no C8 C9 C10 C11 -1.3(4) . . . . no C12 C9 C10 C11 -179.4(3) . . . . no C9 C10 C11 N4 0.8(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 O1 O6 3.224(4) . 3_555 no O1 N6 3.026(4) . 3_554 no O1 N3 2.751(4) . . no O1 C7 3.388(4) . . no O2 O8 3.144(5) . . no O2 N3 3.064(5) . 3_545 no O2 N6 2.774(4) . . no O3 O5 2.591(3) . . no O3 C1 3.333(4) . 2_654 no O3 N8 3.077(4) . 3_544 no O4 C1 3.398(4) . 2_654 no O4 N1 2.582(3) . 2_654 no O5 O3 2.591(3) . . no O5 N5 3.062(3) . 1_554 no O6 O1 3.224(4) . 3_544 no O6 N7 3.023(4) . 3_545 no O6 O8 2.560(3) . . no O7 N4 2.568(3) . 3_544 no O8 N2 3.042(4) . 4_455 no O8 O6 2.560(3) . . no O8 O2 3.144(5) . . no O1 H4 2.54(3) . . no O1 H3B 2.59(7) . . no O1 H6A 2.14(5) . 3_554 no O1 H7 2.52(3) . . no O1 H3A 2.65(6) . . no O2 H10 2.61(3) . . no O2 H6B 2.87(7) . . no O2 H3B 2.18(7) . 3_545 no O2 H2 2.87(3) . 4_455 no O2 H6A 2.72(5) . . no O3 H8A 2.28(4) . 3_544 no O3 H1 2.54(4) . 2_654 no O3 H5O 1.72(5) . . no O4 H18 2.33(3) . . no O4 H11 2.62(3) . 4_554 no O5 H25 2.82(4) . . no O5 H5N 2.17(4) . 1_554 no O6 H6B 2.62(8) . . no O6 H7B 2.05(8) . 3_545 no O6 H8O 1.66(5) . . no O7 H25 2.46(3) . . no O7 H5 2.68(4) . . no O8 H2N 2.25(4) . 4_455 no O8 H3A 2.67(6) . 3_544 no N1 C19 3.336(4) . 2_655 no N1 O4 2.582(3) . 2_655 no N2 O8 3.042(4) . 4_555 no N3 O2 3.064(5) . 3_554 no N3 N7 3.126(4) . 2_665 no N3 O1 2.751(4) . . no N4 O7 2.568(3) . 3_555 no N4 C26 3.319(4) . 3_555 no N5 O5 3.062(3) . 1_556 no N6 O1 3.026(4) . 3_545 no N6 O2 2.774(4) . . no N6 N8 3.181(4) . 3_545 no N7 N3 3.126(4) . 2_664 no N7 O6 3.023(4) . 3_554 no N8 O3 3.077(4) . 3_555 no N8 N6 3.181(4) . 3_554 no N8 C11 3.336(5) . 1_554 no N1 H4O 1.56(5) . 2_655 no N2 H2 2.65(3) . . no N3 H7A 2.31(3) . 2_665 no N4 H7O 1.54(7) . 3_555 no N5 H8 2.66(5) . . no N6 H8B 2.19(4) . 3_545 no C1 O4 3.398(4) . 2_655 no C1 C18 3.593(5) . 1_556 no C1 C13 3.363(5) . 1_556 no C1 O3 3.333(4) . 2_655 no C2 C17 3.577(5) . 1_556 no C3 C17 3.467(4) . . no C3 C16 3.575(4) . 1_556 no C3 C15 3.463(4) . 1_556 no C4 C17 3.567(4) . . no C5 C13 3.470(5) . . no C7 O1 3.388(4) . . no C7 C23 3.448(5) . . no C7 C24 3.564(5) . . no C8 C23 3.520(4) . . no C8 C25 3.584(4) . . no C8 C24 3.525(4) . . no C9 C22 3.584(5) . . no C9 C21 3.564(4) . . no C10 C23 3.385(4) . 1_556 no C10 C22 3.479(5) . 1_556 no C11 N8 3.336(5) . 1_556 no C11 C23 3.380(5) . 1_556 no C12 C21 3.532(5) . . no C13 C5 3.470(5) . . no C13 C1 3.363(5) . 1_554 no C15 C25 3.563(4) . . no C15 C3 3.463(4) . 1_554 no C16 C3 3.575(4) . 1_554 no C17 C3 3.467(4) . . no C17 C4 3.567(4) . . no C17 C2 3.577(5) . 1_554 no C18 C1 3.593(5) . 1_554 no C19 N1 3.336(4) . 2_654 no C21 C12 3.532(5) . . no C21 C9 3.564(4) . . no C22 C9 3.584(5) . . no C22 C10 3.479(5) . 1_554 no C23 C11 3.380(5) . 1_554 no C23 C10 3.385(4) . 1_554 no C23 C8 3.520(4) . . no C23 C7 3.448(5) . . no C24 C7 3.564(5) . . no C24 C8 3.525(4) . . no C25 C15 3.563(4) . . no C25 C8 3.584(4) . . no C26 N4 3.319(4) . 3_544 no C1 H4O 2.47(5) . 2_655 no C1 H22 2.94(4) . 4_555 no C2 H22 2.91(4) . 4_555 no C2 H2N 2.61(3) . . no C4 H25 3.02(4) . . no C5 H4O 2.56(5) . 2_655 no C7 H15 2.80(4) . 1_556 no C7 H7O 2.49(7) . 3_555 no C8 H5N 2.66(4) . . no C8 H15 2.74(4) . 1_556 no C10 H2 3.03(4) . 4_455 no C11 H1 2.93(4) . 4_455 no C11 H7O 2.52(7) . 3_555 no C14 H25 2.90(4) . . no C15 H25 2.91(4) . . no C17 H10 2.98(4) . 4_554 no C18 H10 2.77(4) . 4_554 no C19 H5O 2.24(5) . . no C22 H18 3.00(3) . 4_455 no C24 H4 3.01(4) . . no C25 H4 2.85(4) . . no C26 H8O 2.22(4) . . no H1 O3 2.54(4) . 2_655 no H1 C11 2.93(4) . 4_555 no H1 H4O 2.36(6) . 2_655 no H2 N2 2.65(3) . . no H2 C10 3.03(4) . 4_555 no H2 O2 2.87(3) . 4_555 no H2 H2N 2.17(5) . . no H2N H2 2.17(5) . . no H2N C2 2.61(3) . . no H2N O8 2.25(4) . 4_555 no H3A H8O 2.51(8) . 3_555 no H3A O8 2.67(6) . 3_555 no H3A O1 2.65(6) . . no H3B O2 2.18(7) . 3_554 no H3B O1 2.59(7) . . no H4 C25 2.85(4) . . no H4 H25 2.42(5) . . no H4 O1 2.54(3) . . no H4 C24 3.01(4) . . no H4O H1 2.36(6) . 2_654 no H4O N1 1.56(5) . 2_654 no H4O C1 2.47(5) . 2_654 no H4O C5 2.56(5) . 2_654 no H5 O7 2.68(4) . . no H5N C8 2.66(4) . . no H5N O5 2.17(4) . 1_556 no H5N H8 2.27(6) . . no H5O C19 2.24(5) . . no H5O O3 1.72(5) . . no H6A O1 2.14(5) . 3_545 no H6A O2 2.72(5) . . no H6B O2 2.87(7) . . no H6B O6 2.62(8) . . no H6B H7B 2.58(12) . 3_545 no H6B H8B 2.39(8) . 3_545 no H7 O1 2.52(3) . . no H7A N3 2.31(3) . 2_664 no H7A H17 2.46(5) . . no H7B O6 2.05(8) . 3_554 no H7B H15 2.46(9) . . no H7B H6B 2.58(12) . 3_554 no H7O C7 2.49(7) . 3_544 no H7O N4 1.54(7) . 3_544 no H7O C11 2.52(7) . 3_544 no H8 N5 2.66(5) . . no H8 H5N 2.27(6) . . no H8A H22 2.30(5) . . no H8A O3 2.28(4) . 3_555 no H8B N6 2.19(4) . 3_554 no H8B H6B 2.39(8) . 3_554 no H8B H24 2.42(5) . . no H8O C26 2.22(4) . . no H8O H3A 2.51(8) . 3_544 no H8O O6 1.66(5) . . no H10 C18 2.77(4) . 4_456 no H10 O2 2.61(3) . . no H10 C17 2.98(4) . 4_456 no H10 H18 2.52(5) . 4_456 no H11 O4 2.62(3) . 4_456 no H15 C8 2.74(4) . 1_554 no H15 H7B 2.46(9) . . no H15 C7 2.80(4) . 1_554 no H17 H7A 2.46(5) . . no H18 H22 2.45(5) . 4_555 no H18 C22 3.00(3) . 4_555 no H18 H10 2.52(5) . 4_554 no H18 O4 2.33(3) . . no H22 C2 2.91(4) . 4_455 no H22 H8A 2.30(5) . . no H22 C1 2.94(4) . 4_455 no H22 H18 2.45(5) . 4_455 no H24 H8B 2.42(5) . . no H25 H4 2.42(5) . . no H25 O5 2.82(4) . . no H25 O7 2.46(3) . . no H25 C4 3.02(4) . . no H25 C14 2.90(4) . . no H25 C15 2.91(4) . . no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # N2 H2N O8 0.86(4) 2.25(4) 3.042(4) 154(4) 4_555 yes N3 H3B O2 0.96(6) 2.18(7) 3.064(5) 153(5) 3_554 yes O4 H4O N1 1.03(5) 1.56(5) 2.582(3) 170(5) 2_654 yes N5 H5N O5 0.91(4) 2.17(4) 3.062(3) 168(4) 1_556 yes O5 H5O O3 0.92(5) 1.72(5) 2.591(3) 156(4) . yes N6 H6A O1 0.96(5) 2.14(5) 3.026(4) 153(4) 3_545 yes N7 H7A N3 0.84(3) 2.31(3) 3.126(4) 166(3) 2_664 yes N7 H7B O6 1.08(8) 2.05(8) 3.023(4) 148(6) 3_554 yes O7 H7O N4 1.03(7) 1.54(7) 2.568(3) 177(10) 3_544 yes N8 H8A O3 0.90(4) 2.28(4) 3.077(4) 148(3) 3_555 yes N8 H8B N6 1.02(4) 2.19(4) 3.181(4) 162(3) 3_554 yes O8 H8O O6 0.94(5) 1.66(5) 2.560(3) 158(4) . yes C1 H1 O3 1.07(4) 2.54(4) 3.333(4) 130(3) 2_655 yes C7 H7 O1 0.87(3) 2.52(3) 3.388(4) 177(3) . yes C18 H18 O4 0.98(3) 2.33(3) 2.758(4) 106(2) . yes #===END # Attachment '3094_web_deposit_cif_file_9_PawelGrobelny_1289286463.cif' # CIF-file generated for datamm in Pna2(1) #=============================================================================== data_datam10 _database_code_depnum_ccdc_archive 'CCDC 800239' #TrackingRef '3094_web_deposit_cif_file_9_PawelGrobelny_1289286463.cif' #=============================================================================== _chemical_name_systematic ; ; _chemical_name_common 'Isoniazid:4-aminosalicylic acid co-crystal' _chemical_melting_point ? _chemical_formula_moiety 'C7 H7 N O3, C6 H7 N3 O' _chemical_formula_structural ? _chemical_formula_sum 'C13 H14 N4 O4' _chemical_formula_iupac ? _chemical_formula_weight 290.28 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_space_group_name_H-M 'P n a 21' _symmetry_Int_Tables_number 33 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,1/2+z 3 1/2-x,1/2+y,1/2+z 4 1/2+x,1/2-y,z _cell_length_a 21.942(2) _cell_length_b 16.515(2) _cell_length_c 7.3435(8) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2661.1(5) _cell_formula_units_Z 8 _cell_measurement_temperature 280 _cell_measurement_reflns_used 6233 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 27.5 _cell_special_details ; ; _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.449 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 0.110 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.9572 _exptl_absorpt_correction_T_max 0.9837 #=============================================================================== _exptl_special_details ; ; _diffrn_ambient_temperature 280 _diffrn_source_power 0.6 _diffrn_source_voltage 50.0 _diffrn_source_current 12.0 _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_source 'Sealed Tube' _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_measurement_specimen_support Fiber _diffrn_detector CCD _diffrn_measurement_device ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_detector_area_resol_mean 13.6612 _diffrn_measurement_method 'profile data from \w-scans' _diffrn_reflns_number 27333 _diffrn_reflns_av_R_equivalents 0.0582 _diffrn_reflns_av_sigmaI/netI 0.0264 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3298 _reflns_number_gt 2992 _reflns_threshold_expression >2\s(I) _refine_diff_density_max 0.196 _refine_diff_density_min -0.181 _refine_diff_density_rms 0.057 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measurement_details ; scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 0.0000 XTD: 49.4255 2theta: 29.5752 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 120.0000 XTD: 49.4255 2theta: 29.5752 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 240.0000 XTD: 49.4255 2theta: 29.5752 ; _diffrn_orient_matrix_UB_11 0.015029 _diffrn_orient_matrix_UB_12 -0.134298 _diffrn_orient_matrix_UB_13 0.016789 _diffrn_orient_matrix_UB_21 0.060103 _diffrn_orient_matrix_UB_22 0.007002 _diffrn_orient_matrix_UB_23 0.002210 _diffrn_orient_matrix_UB_31 -0.002291 _diffrn_orient_matrix_UB_32 0.005394 _diffrn_orient_matrix_UB_33 0.045196 _diffrn_orient_matrix_type d*Trek _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== _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^ > 2\s(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^)+(0.0761P)^2^+0.2437P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3298 _refine_ls_number_parameters 492 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0551 _refine_ls_R_factor_gt 0.0471 _refine_ls_wR_factor_ref 0.1393 _refine_ls_wR_factor_gt 0.1262 _refine_ls_goodness_of_fit_ref 1.182 _refine_ls_restrained_S_all 1.182 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 #=============================================================================== loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags O3 O Uani 0.42365(10) 0.00483(13) 0.1154(5) 1.000 0.0632(8) . . O4 O Uani 0.51998(10) 0.03866(14) 0.1736(5) 1.000 0.0600(8) . . O5 O Uani 0.34691(9) 0.11889(14) 0.0386(4) 1.000 0.0528(8) . . N7 N Uani 0.40849(15) 0.39157(17) 0.1419(6) 1.000 0.0595(12) . . C13 C Uani 0.44843(12) 0.14297(17) 0.1494(4) 1.000 0.0379(8) . . C14 C Uani 0.39094(12) 0.17164(18) 0.0939(4) 1.000 0.0393(8) . . C15 C Uani 0.37803(13) 0.25337(18) 0.0914(4) 1.000 0.0400(9) . . C16 C Uani 0.42183(13) 0.31028(17) 0.1428(5) 1.000 0.0405(9) . . C17 C Uani 0.47922(14) 0.28292(18) 0.2029(4) 1.000 0.0419(9) . . C18 C Uani 0.49179(12) 0.20080(18) 0.2038(4) 1.000 0.0390(9) . . C19 C Uani 0.46289(13) 0.05663(18) 0.1462(5) 1.000 0.0448(9) . . O6 O Uani 0.18269(11) 0.00845(14) 0.4797(5) 1.000 0.0620(9) . . O7 O Uani 0.27791(10) 0.03915(13) 0.4005(5) 1.000 0.0588(8) . . O8 O Uani 0.10174(10) 0.11974(17) 0.4899(4) 1.000 0.0584(9) . . N8 N Uani 0.16845(16) 0.39385(18) 0.4204(6) 1.000 0.0579(10) . . C20 C Uani 0.20689(12) 0.14572(16) 0.4183(4) 1.000 0.0374(8) . . C21 C Uani 0.14757(13) 0.17307(19) 0.4537(5) 1.000 0.0426(9) . . C22 C Uani 0.13510(14) 0.2554(2) 0.4541(5) 1.000 0.0451(10) . . C23 C Uani 0.18005(13) 0.31224(18) 0.4173(5) 1.000 0.0430(9) . . C24 C Uani 0.23886(14) 0.28440(19) 0.3733(5) 1.000 0.0429(10) . . C25 C Uani 0.25126(14) 0.20348(18) 0.3734(4) 1.000 0.0398(9) . . C26 C Uani 0.22175(14) 0.05904(18) 0.4342(5) 1.000 0.0451(9) . . O1 O Uani 0.37673(10) 0.39721(14) 0.6637(5) 1.000 0.0618(9) . . N1 N Uani 0.45726(12) 0.11482(15) 0.6612(4) 1.000 0.0460(8) . . N2 N Uani 0.47714(12) 0.41864(16) 0.6515(6) 1.000 0.0582(12) . . N3 N Uani 0.47252(15) 0.50416(18) 0.6497(9) 1.000 0.0713(15) . . C1 C Uani 0.50089(14) 0.1647(2) 0.7201(5) 1.000 0.0472(10) . . C2 C Uani 0.49503(13) 0.24778(19) 0.7219(5) 1.000 0.0416(9) . . C3 C Uani 0.44078(12) 0.28161(16) 0.6618(4) 1.000 0.0378(8) . . C4 C Uani 0.39485(14) 0.2302(2) 0.6028(5) 1.000 0.0444(9) . . C5 C Uani 0.40480(14) 0.1478(2) 0.6042(5) 1.000 0.0475(10) . . C6 C Uani 0.42850(13) 0.37092(19) 0.6586(5) 1.000 0.0449(9) . . O2 O Uani 0.11406(11) 0.10723(14) 0.9181(5) 1.000 0.0632(9) . . N4 N Uani 0.20144(11) 0.38567(14) 0.9095(5) 1.000 0.0457(8) . . N5 N Uani 0.21483(13) 0.08215(15) 0.9326(5) 1.000 0.0489(9) . . N6 N Uani 0.20922(16) -0.00350(17) 0.9311(7) 1.000 0.0605(12) . . C7 C Uani 0.24280(14) 0.33451(19) 0.8457(5) 1.000 0.0446(9) . . C8 C Uani 0.23451(13) 0.25109(19) 0.8476(5) 1.000 0.0409(10) . . C9 C Uani 0.18093(12) 0.22079(15) 0.9182(4) 1.000 0.0370(8) . . C10 C Uani 0.13734(13) 0.2740(2) 0.9814(5) 1.000 0.0412(9) . . C11 C Uani 0.14907(13) 0.35668(19) 0.9757(5) 1.000 0.0454(9) . . C12 C Uani 0.16700(13) 0.13101(18) 0.9232(5) 1.000 0.0417(8) . . H4O H Uiso 0.530(3) -0.018(3) 0.164(10) 1.000 0.11(2) . . H5O H Uiso 0.3629(18) 0.068(2) 0.068(7) 1.000 0.065(12) . . H7A H Uiso 0.4390(19) 0.429(3) 0.156(7) 1.000 0.067(12) . . H7B H Uiso 0.372(3) 0.410(4) 0.068(11) 1.000 0.13(2) . . H15 H Uiso 0.3360(18) 0.270(2) 0.058(6) 1.000 0.059(11) . . H17 H Uiso 0.5105(14) 0.3198(18) 0.229(5) 1.000 0.036(8) . . H18 H Uiso 0.5281(13) 0.1749(17) 0.246(4) 1.000 0.030(8) . . H7O H Uiso 0.287(3) -0.027(4) 0.405(11) 1.000 0.14(2) . . H8A H Uiso 0.135(2) 0.409(2) 0.467(7) 1.000 0.063(13) . . H8B H Uiso 0.200(2) 0.430(3) 0.417(7) 1.000 0.074(14) . . H8O H Uiso 0.132(3) 0.071(3) 0.491(10) 1.000 0.12(2) . . H22 H Uiso 0.1029(19) 0.276(2) 0.485(6) 1.000 0.064(12) . . H24 H Uiso 0.2698(19) 0.323(3) 0.353(7) 1.000 0.072(14) . . H25 H Uiso 0.2934(16) 0.182(2) 0.351(6) 1.000 0.054(10) . . H1 H Uiso 0.5362(14) 0.129(2) 0.759(5) 1.000 0.042(9) . . H2 H Uiso 0.5269(18) 0.281(2) 0.760(6) 1.000 0.064(12) . . H2N H Uiso 0.5132(18) 0.400(2) 0.625(7) 1.000 0.063(12) . . H3A H Uiso 0.443(3) 0.518(4) 0.546(10) 1.000 0.12(2) . . H3B H Uiso 0.455(3) 0.513(4) 0.751(10) 1.000 0.10(2) . . H4 H Uiso 0.3544(18) 0.253(2) 0.564(6) 1.000 0.065(12) . . H5 H Uiso 0.3754(16) 0.109(2) 0.569(6) 1.000 0.050(10) . . H5N H Uiso 0.256(2) 0.098(3) 0.950(8) 1.000 0.086(15) . . H6A H Uiso 0.186(3) -0.018(3) 1.032(8) 1.000 0.089(17) . . H6B H Uiso 0.190(3) -0.023(4) 0.835(9) 1.000 0.10(2) . . H7 H Uiso 0.2766(14) 0.3506(18) 0.802(5) 1.000 0.033(8) . . H8 H Uiso 0.2623(17) 0.218(2) 0.801(6) 1.000 0.051(10) . . H10 H Uiso 0.1000(16) 0.253(2) 1.037(5) 1.000 0.049(10) . . H11 H Uiso 0.1186(17) 0.401(2) 1.029(6) 1.000 0.055(10) . . 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 O3 0.0421(11) 0.0416(11) 0.106(2) -0.0085(14) -0.0055(14) -0.0065(9) O4 0.0366(10) 0.0424(11) 0.101(2) 0.0028(15) -0.0058(14) 0.0003(9) O5 0.0325(10) 0.0487(12) 0.0773(17) -0.0020(12) -0.0092(11) -0.0078(9) N7 0.0565(18) 0.0359(13) 0.086(3) -0.0001(16) -0.0083(18) 0.0008(12) C13 0.0338(12) 0.0357(13) 0.0443(15) -0.0017(13) 0.0013(12) -0.0042(10) C14 0.0309(13) 0.0458(16) 0.0412(14) 0.0016(13) 0.0019(12) -0.0056(11) C15 0.0308(12) 0.0454(16) 0.0437(16) 0.0048(13) -0.0012(12) -0.0006(11) C16 0.0417(15) 0.0379(14) 0.0420(16) 0.0004(13) 0.0016(13) -0.0003(11) C17 0.0386(14) 0.0409(15) 0.0463(17) -0.0045(14) -0.0020(14) -0.0068(12) C18 0.0301(13) 0.0421(14) 0.0449(17) -0.0032(14) -0.0007(12) -0.0016(11) C19 0.0359(14) 0.0410(15) 0.0576(18) -0.0006(15) -0.0015(14) -0.0039(11) O6 0.0481(13) 0.0398(11) 0.098(2) -0.0002(13) 0.0069(14) -0.0108(10) O7 0.0448(12) 0.0336(10) 0.098(2) 0.0061(13) 0.0126(14) 0.0037(8) O8 0.0310(10) 0.0620(15) 0.0823(19) 0.0085(14) 0.0027(11) -0.0059(10) N8 0.0554(18) 0.0424(15) 0.076(2) -0.0035(16) 0.0055(18) 0.0158(14) C20 0.0306(12) 0.0381(14) 0.0435(14) -0.0010(13) 0.0010(12) 0.0005(10) C21 0.0303(13) 0.0505(17) 0.0471(17) 0.0039(14) -0.0025(12) -0.0032(11) C22 0.0326(14) 0.055(2) 0.0478(17) 0.0039(15) 0.0016(13) 0.0106(13) C23 0.0421(15) 0.0444(15) 0.0425(15) 0.0015(14) -0.0001(14) 0.0106(12) C24 0.0375(15) 0.0386(16) 0.0527(19) -0.0013(14) 0.0034(14) 0.0015(12) C25 0.0333(14) 0.0379(14) 0.0481(18) -0.0041(13) 0.0020(13) 0.0010(11) C26 0.0407(15) 0.0380(15) 0.0566(19) -0.0036(15) -0.0002(14) -0.0048(12) O1 0.0370(11) 0.0484(12) 0.100(2) 0.0097(15) 0.0100(14) 0.0076(9) N1 0.0420(13) 0.0395(12) 0.0566(16) -0.0018(13) 0.0015(12) 0.0001(10) N2 0.0359(13) 0.0388(13) 0.100(3) 0.0000(17) 0.0094(17) 0.0037(10) N3 0.0509(16) 0.0379(14) 0.125(4) 0.005(2) 0.008(2) 0.0008(12) C1 0.0396(15) 0.0481(16) 0.0539(19) 0.0082(16) -0.0025(14) 0.0023(13) C2 0.0327(13) 0.0425(16) 0.0497(19) 0.0006(14) -0.0028(13) 0.0001(12) C3 0.0320(13) 0.0431(14) 0.0384(14) 0.0001(13) 0.0048(12) 0.0008(10) C4 0.0314(13) 0.0520(16) 0.0499(17) 0.0002(15) -0.0006(13) 0.0009(12) C5 0.0364(15) 0.0461(16) 0.060(2) -0.0050(16) -0.0017(14) -0.0076(13) C6 0.0338(14) 0.0454(15) 0.0555(19) 0.0042(16) 0.0074(14) 0.0049(12) O2 0.0374(12) 0.0481(13) 0.104(2) 0.0043(15) -0.0044(14) -0.0110(9) N4 0.0427(14) 0.0341(12) 0.0604(16) 0.0042(13) -0.0067(13) -0.0029(10) N5 0.0402(14) 0.0315(12) 0.075(2) 0.0012(14) -0.0066(14) -0.0038(10) N6 0.0590(18) 0.0315(13) 0.091(3) 0.0014(17) -0.006(2) -0.0032(11) C7 0.0341(14) 0.0407(15) 0.0591(19) 0.0031(15) 0.0025(14) -0.0063(12) C8 0.0339(14) 0.0415(17) 0.0474(19) -0.0025(13) 0.0011(12) 0.0003(12) C9 0.0332(13) 0.0352(13) 0.0425(14) 0.0008(13) -0.0045(12) -0.0044(10) C10 0.0294(12) 0.0428(15) 0.0515(17) -0.0012(14) -0.0009(12) -0.0029(11) C11 0.0376(15) 0.0411(15) 0.0576(19) -0.0024(14) -0.0049(14) 0.0016(12) C12 0.0395(15) 0.0376(13) 0.0481(16) 0.0001(14) -0.0035(13) -0.0045(11) #=============================================================================== _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; 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 O3 C19 1.235(4) . . yes O4 C19 1.303(4) . . yes O5 C14 1.363(4) . . yes O4 H4O 0.96(5) . . no O5 H5O 0.94(4) . . no O6 C26 1.243(4) . . yes O7 C26 1.299(4) . . yes O8 C21 1.363(4) . . yes O7 H7O 1.11(7) . . no O8 H8O 1.04(6) . . no O1 C6 1.217(4) . . yes O2 C12 1.227(4) . . yes N7 C16 1.374(4) . . yes N7 H7A 0.92(5) . . no N7 H7B 1.01(7) . . no N8 C23 1.372(4) . . yes N8 H8B 0.91(5) . . no N8 H8A 0.85(5) . . no N1 C5 1.341(4) . . yes N1 C1 1.335(4) . . yes N2 C6 1.328(4) . . yes N2 N3 1.416(4) . . yes N2 H2N 0.87(4) . . no N3 H3B 0.85(7) . . no N3 H3A 1.03(7) . . no N4 C11 1.336(4) . . yes N4 C7 1.326(4) . . yes N5 C12 1.326(4) . . yes N5 N6 1.420(4) . . yes N5 H5N 0.95(5) . . no N6 H6A 0.93(6) . . no N6 H6B 0.88(6) . . no C13 C14 1.408(4) . . no C13 C19 1.461(4) . . no C13 C18 1.406(4) . . no C14 C15 1.379(4) . . no C15 C16 1.396(4) . . no C16 C17 1.409(4) . . no C17 C18 1.384(4) . . no C15 H15 0.99(4) . . no C17 H17 0.94(3) . . no C18 H18 0.96(3) . . no C20 C26 1.473(4) . . no C20 C25 1.402(4) . . no C20 C21 1.402(4) . . no C21 C22 1.387(5) . . no C22 C23 1.388(4) . . no C23 C24 1.408(4) . . no C24 C25 1.364(4) . . no C22 H22 0.82(4) . . no C24 H24 0.94(5) . . no C25 H25 1.00(4) . . no C1 C2 1.378(5) . . no C2 C3 1.387(4) . . no C3 C4 1.387(4) . . no C3 C6 1.500(4) . . no C4 C5 1.378(5) . . no C1 H1 1.02(3) . . no C2 H2 0.93(4) . . no C4 H4 1.01(4) . . no C5 H5 0.95(3) . . no C7 C8 1.390(4) . . no C8 C9 1.379(4) . . no C9 C10 1.379(4) . . no C9 C12 1.514(4) . . no C10 C11 1.390(5) . . no C7 H7 0.85(3) . . no C8 H8 0.89(4) . . no C10 H10 0.98(4) . . no C11 H11 1.07(4) . . 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 C19 O4 H4O 115(4) . . . no C14 O5 H5O 104(2) . . . no C26 O7 H7O 114(3) . . . no C21 O8 H8O 92(3) . . . no C16 N7 H7A 120(3) . . . no H7A N7 H7B 116(5) . . . no C16 N7 H7B 118(4) . . . no C23 N8 H8B 120(3) . . . no C23 N8 H8A 117(2) . . . no H8A N8 H8B 118(4) . . . no C1 N1 C5 117.8(3) . . . yes N3 N2 C6 122.3(3) . . . yes N3 N2 H2N 115(2) . . . no C6 N2 H2N 122(2) . . . no H3A N3 H3B 109(6) . . . no N2 N3 H3A 106(4) . . . no N2 N3 H3B 101(4) . . . no C7 N4 C11 119.3(3) . . . yes N6 N5 C12 122.5(3) . . . yes C12 N5 H5N 126(3) . . . no N6 N5 H5N 111(3) . . . no N5 N6 H6B 114(4) . . . no N5 N6 H6A 107(3) . . . no H6A N6 H6B 106(6) . . . no C14 C13 C18 117.4(3) . . . no C18 C13 C19 121.4(2) . . . no C14 C13 C19 121.2(3) . . . no O5 C14 C15 118.4(2) . . . yes C13 C14 C15 121.1(3) . . . no O5 C14 C13 120.4(3) . . . yes C14 C15 C16 120.9(3) . . . no C15 C16 C17 119.0(3) . . . no N7 C16 C15 120.7(3) . . . yes N7 C16 C17 120.4(3) . . . yes C16 C17 C18 119.6(3) . . . no C13 C18 C17 122.0(3) . . . no O4 C19 C13 115.4(3) . . . yes O3 C19 C13 121.9(3) . . . yes O3 C19 O4 122.8(3) . . . yes C16 C15 H15 121(2) . . . no C14 C15 H15 117.7(19) . . . no C18 C17 H17 119.3(18) . . . no C16 C17 H17 120.7(18) . . . no C13 C18 H18 110.6(17) . . . no C17 C18 H18 127.3(17) . . . no C25 C20 C26 121.7(3) . . . no C21 C20 C26 120.3(3) . . . no C21 C20 C25 118.0(3) . . . no O8 C21 C22 119.2(3) . . . yes C20 C21 C22 120.0(3) . . . no O8 C21 C20 120.9(3) . . . yes C21 C22 C23 121.5(3) . . . no N8 C23 C22 122.0(3) . . . yes N8 C23 C24 119.7(3) . . . yes C22 C23 C24 118.4(3) . . . no C23 C24 C25 120.2(3) . . . no C20 C25 C24 121.9(3) . . . no O7 C26 C20 116.2(3) . . . yes O6 C26 O7 122.4(3) . . . yes O6 C26 C20 121.5(3) . . . yes C21 C22 H22 125(2) . . . no C23 C22 H22 113(2) . . . no C25 C24 H24 121(3) . . . no C23 C24 H24 118(3) . . . no C20 C25 H25 116(2) . . . no C24 C25 H25 122.0(19) . . . no N1 C1 C2 123.4(3) . . . yes C1 C2 C3 118.6(3) . . . no C2 C3 C6 123.7(3) . . . no C2 C3 C4 118.5(3) . . . no C4 C3 C6 117.8(3) . . . no C3 C4 C5 119.1(3) . . . no N1 C5 C4 122.7(3) . . . yes N2 C6 C3 116.1(3) . . . yes O1 C6 C3 121.2(3) . . . yes O1 C6 N2 122.7(3) . . . yes N1 C1 H1 106.3(19) . . . no C2 C1 H1 130.3(19) . . . no C3 C2 H2 120(2) . . . no C1 C2 H2 121(2) . . . no C3 C4 H4 120(2) . . . no C5 C4 H4 121(2) . . . no N1 C5 H5 113(2) . . . no C4 C5 H5 124(2) . . . no N4 C7 C8 122.6(3) . . . yes C7 C8 C9 118.4(3) . . . no C8 C9 C10 119.1(3) . . . no C10 C9 C12 118.4(3) . . . no C8 C9 C12 122.5(3) . . . no C9 C10 C11 119.2(3) . . . no N4 C11 C10 121.5(3) . . . yes O2 C12 C9 120.3(3) . . . yes N5 C12 C9 115.9(2) . . . yes O2 C12 N5 123.8(3) . . . yes N4 C7 H7 122(2) . . . no C8 C7 H7 115(2) . . . no C7 C8 H8 121(2) . . . no C9 C8 H8 121(2) . . . no C9 C10 H10 120(2) . . . no C11 C10 H10 121(2) . . . no N4 C11 H11 115.3(19) . . . no C10 C11 H11 123.2(19) . . . 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N1 C5 C4 0.6(5) . . . . no C5 N1 C1 C2 -1.2(5) . . . . no N3 N2 C6 C3 -179.3(4) . . . . no N3 N2 C6 O1 0.1(7) . . . . no C11 N4 C7 C8 -1.2(6) . . . . no C7 N4 C11 C10 0.9(6) . . . . no N6 N5 C12 C9 -177.5(4) . . . . no N6 N5 C12 O2 2.3(6) . . . . no C14 C13 C18 C17 -0.3(4) . . . . no C19 C13 C18 C17 178.3(3) . . . . no C19 C13 C14 O5 1.1(4) . . . . no C14 C13 C19 O4 169.9(3) . . . . no C18 C13 C19 O4 -8.6(5) . . . . no C14 C13 C19 O3 -8.5(5) . . . . no C18 C13 C14 O5 179.7(3) . . . . no C19 C13 C14 C15 -177.9(3) . . . . no C18 C13 C14 C15 0.7(4) . . . . no C18 C13 C19 O3 173.0(3) . . . . no C13 C14 C15 C16 0.4(5) . . . . no O5 C14 C15 C16 -178.6(3) . . . . no C14 C15 C16 C17 -1.9(5) . . . . no C14 C15 C16 N7 -179.3(3) . . . . no C15 C16 C17 C18 2.3(5) . . . . no N7 C16 C17 C18 179.7(3) . . . . no C16 C17 C18 C13 -1.2(5) . . . . no C26 C20 C21 C22 174.4(3) . . . . no C25 C20 C26 O7 -1.4(5) . . . . no C26 C20 C21 O8 -4.9(5) . . . . no C25 C20 C21 C22 -3.7(5) . . . . no C26 C20 C25 C24 -174.5(3) . . . . no C21 C20 C26 O6 -0.4(5) . . . . no C21 C20 C25 C24 3.6(5) . . . . no C25 C20 C26 O6 177.7(3) . . . . no C25 C20 C21 O8 177.0(3) . . . . no C21 C20 C26 O7 -179.4(3) . . . . no O8 C21 C22 C23 -179.7(3) . . . . no C20 C21 C22 C23 1.0(5) . . . . no C21 C22 C23 C24 2.0(5) . . . . no C21 C22 C23 N8 -178.9(4) . . . . no N8 C23 C24 C25 178.7(4) . . . . no C22 C23 C24 C25 -2.2(5) . . . . no C23 C24 C25 C20 -0.6(5) . . . . no N1 C1 C2 C3 0.9(5) . . . . no C1 C2 C3 C4 0.1(5) . . . . no C1 C2 C3 C6 179.4(3) . . . . no C4 C3 C6 O1 23.8(5) . . . . no C2 C3 C4 C5 -0.6(5) . . . . no C4 C3 C6 N2 -156.7(4) . . . . no C2 C3 C6 N2 23.9(5) . . . . no C6 C3 C4 C5 -180.0(3) . . . . no C2 C3 C6 O1 -155.5(4) . . . . no C3 C4 C5 N1 0.3(5) . . . . no N4 C7 C8 C9 0.3(5) . . . . no C7 C8 C9 C10 1.0(5) . . . . no C7 C8 C9 C12 178.8(3) . . . . no C8 C9 C12 N5 28.1(5) . . . . no C10 C9 C12 O2 26.2(5) . . . . no C10 C9 C12 N5 -154.0(3) . . . . no C8 C9 C12 O2 -151.7(4) . . . . no C8 C9 C10 C11 -1.3(5) . . . . no C12 C9 C10 C11 -179.2(3) . . . . no C9 C10 C11 N4 0.4(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 O1 C7 3.390(4) . . no O1 O6 3.234(4) . 3_555 no O1 N6 3.027(5) . 3_554 no O1 N3 2.747(4) . . no O2 N3 3.066(5) . 3_545 no O2 O8 3.163(5) . . no O2 N6 2.777(4) . . no O3 C1 3.342(4) . 2_654 no O3 N8 3.081(4) . 3_544 no O3 O5 2.589(3) . . no O4 C1 3.407(4) . 2_654 no O4 N1 2.585(3) . 2_654 no O5 O3 2.589(3) . . no O5 N5 3.062(4) . 1_554 no O6 O8 2.557(3) . . no O6 O1 3.234(4) . 3_544 no O6 N7 3.025(4) . 3_545 no O7 N4 2.576(3) . 3_544 no O8 N2 3.047(4) . 4_455 no O8 O6 2.557(3) . . no O8 O2 3.163(5) . . no O1 H7 2.54(3) . . no O1 H3B 2.65(7) . . no O1 H3A 2.62(7) . . no O1 H4 2.54(3) . . no O1 H6A 2.19(6) . 3_554 no O2 H6B 2.79(7) . . no O2 H10 2.58(3) . . no O2 H3A 2.15(7) . 3_545 no O2 H2 2.90(4) . 4_455 no O2 H6A 2.73(6) . . no O3 H1 2.60(3) . 2_654 no O3 H8A 2.31(4) . 3_544 no O3 H5O 1.73(4) . . no O4 H11 2.61(4) . 4_554 no O4 H18 2.32(3) . . no O5 H5N 2.13(5) . 1_554 no O5 H25 2.78(4) . . no O6 H8O 1.52(6) . . no O6 H6B 2.67(7) . . no O6 H7B 2.12(7) . 3_545 no O7 H5 2.73(4) . . no O7 H25 2.41(3) . . no O8 H2N 2.21(4) . 4_455 no O8 H3B 2.78(7) . 3_544 no N1 C19 3.332(4) . 2_655 no N1 O4 2.585(3) . 2_655 no N2 O8 3.047(4) . 4_555 no N3 O2 3.066(5) . 3_554 no N3 N7 3.128(5) . 2_665 no N3 O1 2.747(4) . . no N4 C26 3.327(4) . 3_555 no N4 O7 2.576(3) . 3_555 no N5 O5 3.062(4) . 1_556 no N6 N8 3.176(5) . 3_545 no N6 O1 3.027(5) . 3_545 no N6 O2 2.777(4) . . no N7 O6 3.025(4) . 3_554 no N7 N3 3.128(5) . 2_664 no N8 O3 3.081(4) . 3_555 no N8 C11 3.350(6) . 1_554 no N8 N6 3.176(5) . 3_554 no N1 H4O 1.62(5) . 2_655 no N2 H2 2.65(4) . . no N3 H7A 2.23(4) . 2_665 no N4 H7O 1.47(7) . 3_555 no N5 H8 2.66(4) . . no N6 H8B 2.28(5) . 3_545 no N7 H6B 2.95(7) . 3_554 no C1 C13 3.375(5) . 1_556 no C1 O4 3.407(4) . 2_655 no C1 O3 3.342(4) . 2_655 no C2 C17 3.596(5) . 1_556 no C3 C17 3.474(4) . . no C3 C15 3.474(4) . 1_556 no C3 C16 3.588(5) . 1_556 no C4 C17 3.579(5) . . no C4 C25 3.600(4) . . no C5 C13 3.475(5) . . no C7 O1 3.390(4) . . no C7 C23 3.454(5) . . no C7 C24 3.568(5) . . no C8 C23 3.526(5) . . no C8 C24 3.528(5) . . no C8 C25 3.589(5) . . no C9 C22 3.599(5) . . no C9 C21 3.577(5) . . no C10 C22 3.485(5) . 1_556 no C10 C23 3.395(5) . 1_556 no C11 N8 3.350(6) . 1_556 no C11 C23 3.394(5) . 1_556 no C12 C21 3.543(5) . . no C13 C5 3.475(5) . . no C13 C1 3.375(5) . 1_554 no C15 C25 3.564(4) . . no C15 C3 3.474(4) . 1_554 no C16 C3 3.588(5) . 1_554 no C17 C4 3.579(5) . . no C17 C2 3.596(5) . 1_554 no C17 C3 3.474(4) . . no C19 N1 3.332(4) . 2_654 no C21 C9 3.577(5) . . no C21 C12 3.543(5) . . no C22 C9 3.599(5) . . no C22 C10 3.485(5) . 1_554 no C23 C11 3.394(5) . 1_554 no C23 C10 3.395(5) . 1_554 no C23 C7 3.454(5) . . no C23 C8 3.526(5) . . no C24 C8 3.528(5) . . no C24 C7 3.568(5) . . no C25 C15 3.564(4) . . no C25 C4 3.600(4) . . no C25 C8 3.589(5) . . no C26 N4 3.327(4) . 3_544 no C1 H4O 2.55(5) . 2_655 no C1 H22 2.99(4) . 4_555 no C2 H2N 2.64(3) . . no C2 H22 2.96(4) . 4_555 no C4 H25 3.00(4) . . no C5 H4O 2.61(6) . 2_655 no C7 H7O 2.42(7) . 3_555 no C7 H15 2.78(4) . 1_556 no C8 H5N 2.68(5) . . no C8 H15 2.73(4) . 1_556 no C10 H2 3.06(4) . 4_455 no C11 H7O 2.44(7) . 3_555 no C11 H1 2.95(3) . 4_455 no C14 H25 2.86(4) . . no C15 H25 2.91(4) . . no C17 H10 2.98(4) . 4_554 no C18 H10 2.78(4) . 4_554 no C19 H5O 2.28(4) . . no C22 H18 3.03(3) . 4_455 no C24 H4 2.94(4) . . no C25 H4 2.78(4) . . no C26 H8O 2.02(7) . . no H1 H4O 2.44(7) . 2_655 no H1 C11 2.95(3) . 4_555 no H1 O3 2.60(3) . 2_655 no H2 N2 2.65(4) . . no H2 C10 3.06(4) . 4_555 no H2 H2N 2.22(5) . . no H2 O2 2.90(4) . 4_555 no H2N C2 2.64(3) . . no H2N H2 2.22(5) . . no H2N O8 2.21(4) . 4_555 no H3A O1 2.62(7) . . no H3A O2 2.15(7) . 3_554 no H3B O1 2.65(7) . . no H3B O8 2.78(7) . 3_555 no H4 C25 2.78(4) . . no H4 O1 2.54(3) . . no H4 H25 2.37(6) . . no H4 C24 2.94(4) . . no H4O H1 2.44(7) . 2_654 no H4O C5 2.61(6) . 2_654 no H4O C1 2.55(5) . 2_654 no H4O N1 1.62(5) . 2_654 no H5 O7 2.73(4) . . no H5N C8 2.68(5) . . no H5N H5O 2.55(6) . 1_556 no H5N O5 2.13(5) . 1_556 no H5N H8 2.27(6) . . no H5O O3 1.73(4) . . no H5O H5N 2.55(6) . 1_554 no H5O C19 2.28(4) . . no H6A O1 2.19(6) . 3_545 no H6A O2 2.73(6) . . no H6B O6 2.67(7) . . no H6B N7 2.95(7) . 3_545 no H6B O2 2.79(7) . . no H7 H7O 2.57(7) . 3_555 no H7 O1 2.54(3) . . no H7A N3 2.23(4) . 2_664 no H7A H17 2.45(6) . . no H7B H15 2.44(7) . . no H7B O6 2.12(7) . 3_554 no H7O H11 2.56(8) . 3_544 no H7O N4 1.47(7) . 3_544 no H7O C7 2.42(7) . 3_544 no H7O C11 2.44(7) . 3_544 no H7O H7 2.57(7) . 3_544 no H8 N5 2.66(4) . . no H8 H5N 2.27(6) . . no H8A O3 2.31(4) . 3_555 no H8A H22 2.31(5) . . no H8B N6 2.28(5) . 3_554 no H8B H24 2.39(7) . . no H8O C26 2.02(7) . . no H8O O6 1.52(6) . . no H10 H18 2.50(5) . 4_456 no H10 O2 2.58(3) . . no H10 C18 2.78(4) . 4_456 no H10 C17 2.98(4) . 4_456 no H11 O4 2.61(4) . 4_456 no H11 H7O 2.56(8) . 3_555 no H15 C7 2.78(4) . 1_554 no H15 C8 2.73(4) . 1_554 no H15 H7B 2.44(7) . . no H17 H7A 2.45(6) . . no H18 H10 2.50(5) . 4_554 no H18 H22 2.54(5) . 4_555 no H18 C22 3.03(3) . 4_555 no H18 O4 2.32(3) . . no H22 H8A 2.31(5) . . no H22 C1 2.99(4) . 4_455 no H22 C2 2.96(4) . 4_455 no H22 H18 2.54(5) . 4_455 no H24 H8B 2.39(7) . . no H25 O5 2.78(4) . . no H25 O7 2.41(3) . . no H25 C4 3.00(4) . . no H25 C14 2.86(4) . . no H25 C15 2.91(4) . . no H25 H4 2.37(6) . . no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # N2 H2N O8 0.87(4) 2.21(4) 3.047(4) 162(4) 4_555 yes N3 H3A O2 1.03(7) 2.15(7) 3.066(5) 148(5) 3_554 yes O4 H4O N1 0.96(5) 1.62(5) 2.585(3) 175(11) 2_654 yes N5 H5N O5 0.95(5) 2.13(5) 3.062(4) 168(5) 1_556 yes O5 H5O O3 0.94(4) 1.73(4) 2.589(3) 151(3) . yes N6 H6A O1 0.93(6) 2.19(6) 3.027(5) 149(5) 3_545 yes N7 H7A N3 0.92(5) 2.23(4) 3.128(5) 165(4) 2_664 yes N7 H7B O6 1.01(7) 2.12(7) 3.025(4) 147(5) 3_554 yes O7 H7O N4 1.11(7) 1.47(7) 2.576(3) 179(9) 3_544 yes N8 H8A O3 0.85(5) 2.31(4) 3.081(4) 151(3) 3_555 yes N8 H8B N6 0.91(5) 2.28(5) 3.176(5) 167(4) 3_554 yes O8 H8O O6 1.04(6) 1.52(6) 2.557(3) 172(6) . yes C7 H7 O1 0.85(3) 2.54(3) 3.390(4) 179(4) . yes C18 H18 O4 0.96(3) 2.32(3) 2.757(4) 107(2) . yes C25 H25 O7 1.00(4) 2.41(3) 2.783(4) 101(2) . yes #===END #=============================================================================== data_datam _database_code_depnum_ccdc_archive 'CCDC 800270' #TrackingRef '3097_web_deposit_cif_file_0_PawelGrobelny_1289300182.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common 'Isoniazid:4-aminosalicylic acid co-crystal' _chemical_melting_point ? _chemical_formula_moiety 'C13 H14 N4 O4, C7 H7 N O3, C6 H7 N3 O' _chemical_formula_structural ? _chemical_formula_sum 'C26 H28 N8 O8' _chemical_formula_iupac ? _chemical_formula_weight 580.56 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_space_group_name_H-M 'P n a 21' _symmetry_Int_Tables_number 33 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,1/2+z 3 1/2-x,1/2+y,1/2+z 4 1/2+x,1/2-y,z _cell_length_a 21.840(2) _cell_length_b 16.5060(17) _cell_length_c 7.2541(7) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2615.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150 _cell_measurement_reflns_used 6904 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 27.5 _cell_special_details ; ; _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.475 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 0.112 _exptl_crystal_density_meas_temp ? # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.9565 _exptl_absorpt_correction_T_max 0.9834 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 150 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_source_power 0.6 _diffrn_source_voltage 50.0 _diffrn_source_current 12.0 _diffrn_radiation_wavelength 0.71075 _diffrn_source 'Sealed Tube' _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_measurement_specimen_support Fiber _diffrn_detector CCD _diffrn_measurement_device ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_detector_area_resol_mean 13.6612 _diffrn_measurement_method 'profile data from \w-scans' _diffrn_reflns_number 27056 _diffrn_reflns_av_R_equivalents 0.0513 _diffrn_reflns_av_sigmaI/netI 0.0245 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 27.48 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _reflns_number_total 3246 _reflns_number_gt 3055 _reflns_threshold_expression >2\s(I) _diffrn_measurement_details ; scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 0.0000 XTD: 49.4216 2theta: 29.5586 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 120.0000 XTD: 49.4216 2theta: 29.5586 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 240.0000 XTD: 49.4216 2theta: 29.5586 ; _diffrn_orient_matrix_UB_11 0.015125 _diffrn_orient_matrix_UB_12 -0.135918 _diffrn_orient_matrix_UB_13 0.017353 _diffrn_orient_matrix_UB_21 0.060127 _diffrn_orient_matrix_UB_22 0.007005 _diffrn_orient_matrix_UB_23 0.002461 _diffrn_orient_matrix_UB_31 -0.002501 _diffrn_orient_matrix_UB_32 0.005516 _diffrn_orient_matrix_UB_33 0.045385 _diffrn_orient_matrix_type d*Trek _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _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^ > 2\s(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^)+(0.0791P)^2^+0.2069P] 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 SHELXL _refine_ls_extinction_coef 0.0044(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3246 _refine_ls_number_parameters 493 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0458 _refine_ls_R_factor_gt 0.0401 _refine_ls_wR_factor_ref 0.1262 _refine_ls_wR_factor_gt 0.1095 _refine_ls_goodness_of_fit_ref 1.190 _refine_ls_restrained_S_all 1.190 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.333 _refine_diff_density_min -0.264 _refine_diff_density_rms 0.083 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags O5 O Uani 0.11412(8) 0.10533(11) 0.9154(4) 1.000 0.0370(6) . . O6 O Uani 0.31656(9) 0.50637(11) 0.9868(3) 1.000 0.0364(6) . . O7 O Uani 0.22101(8) 0.53720(10) 0.9011(4) 1.000 0.0361(6) . . O8 O Uani 0.39849(8) 0.61694(12) 0.9906(3) 1.000 0.0355(6) . . N4 N Uani 0.20092(10) 0.38470(12) 0.9103(4) 1.000 0.0291(6) . . N5 N Uani 0.21591(10) 0.08095(12) 0.9299(4) 1.000 0.0298(6) . . N6 N Uani 0.21005(12) -0.00526(12) 0.9282(4) 1.000 0.0365(7) . . N8 N Uani 0.33243(12) 0.89182(13) 0.9186(4) 1.000 0.0347(7) . . C14 C Uani 0.14827(11) 0.35542(15) 0.9761(4) 1.000 0.0289(7) . . C15 C Uani 0.13681(11) 0.27225(16) 0.9814(4) 1.000 0.0266(7) . . C16 C Uani 0.18101(10) 0.21925(13) 0.9178(4) 1.000 0.0234(6) . . C17 C Uani 0.23521(11) 0.25017(15) 0.8471(4) 1.000 0.0257(7) . . C18 C Uani 0.24328(11) 0.33368(15) 0.8455(4) 1.000 0.0287(7) . . C19 C Uani 0.16723(11) 0.12961(14) 0.9219(4) 1.000 0.0265(6) . . C20 C Uani 0.32018(11) 0.81085(14) 0.9168(4) 1.000 0.0279(7) . . C21 C Uani 0.26101(11) 0.78308(15) 0.8709(4) 1.000 0.0266(7) . . C22 C Uani 0.24838(11) 0.70178(15) 0.8727(4) 1.000 0.0266(7) . . C23 C Uani 0.29259(10) 0.64362(14) 0.9184(4) 1.000 0.0249(6) . . C24 C Uani 0.35255(11) 0.67076(15) 0.9546(4) 1.000 0.0267(7) . . C25 C Uani 0.36573(11) 0.75318(16) 0.9547(4) 1.000 0.0280(7) . . C26 C Uani 0.27725(11) 0.55721(14) 0.9371(4) 1.000 0.0285(7) . . O1 O Uani 0.42399(9) 0.00214(10) 0.1149(4) 1.000 0.0383(6) . . O2 O Uani 0.52138(8) 0.03628(11) 0.1703(4) 1.000 0.0364(6) . . O3 O Uani 0.34717(8) 0.11623(11) 0.0362(3) 1.000 0.0332(5) . . N7 N Uani 0.40879(11) 0.38950(13) 0.1445(4) 1.000 0.0356(7) . . C1 C Uani 0.46400(11) 0.05411(15) 0.1437(4) 1.000 0.0284(7) . . C2 C Uani 0.44933(11) 0.14094(14) 0.1477(4) 1.000 0.0252(6) . . C3 C Uani 0.49275(11) 0.19860(15) 0.2044(4) 1.000 0.0252(6) . . C4 C Uani 0.47991(11) 0.28061(15) 0.2050(4) 1.000 0.0275(7) . . C5 C Uani 0.42219(11) 0.30790(14) 0.1444(4) 1.000 0.0264(7) . . C6 C Uani 0.37831(11) 0.25096(15) 0.0913(4) 1.000 0.0263(7) . . C7 C Uani 0.39142(11) 0.16920(15) 0.0927(4) 1.000 0.0260(6) . . O4 O Uani 0.37601(8) 0.39990(12) 0.6693(4) 1.000 0.0378(6) . . N1 N Uani 0.45650(10) 0.11687(13) 0.6592(3) 1.000 0.0289(6) . . N2 N Uani 0.47743(10) 0.42118(13) 0.6509(4) 1.000 0.0359(7) . . N3 N Uani 0.47336(11) 0.50645(14) 0.6521(5) 1.000 0.0423(8) . . C8 C Uani 0.42809(11) 0.37339(15) 0.6609(4) 1.000 0.0274(7) . . C9 C Uani 0.44024(10) 0.28390(14) 0.6622(4) 1.000 0.0248(6) . . C10 C Uani 0.39403(11) 0.23265(17) 0.6008(4) 1.000 0.0281(7) . . C11 C Uani 0.40374(11) 0.14981(16) 0.6009(4) 1.000 0.0300(7) . . C12 C Uani 0.50069(12) 0.16635(15) 0.7198(4) 1.000 0.0291(7) . . C13 C Uani 0.49488(11) 0.24965(16) 0.7232(4) 1.000 0.0271(7) . . H5N H Uiso 0.2559(17) 0.1004(19) 0.946(6) 1.000 0.050(10) . . H6A H Uiso 0.1847(15) -0.0212(19) 1.019(5) 1.000 0.029(8) . . H6B H Uiso 0.214(4) -0.045(5) 0.806(17) 1.000 0.21(4) . . H7O H Uiso 0.210(2) 0.462(3) 0.899(9) 1.000 0.089(16) . . H8A H Uiso 0.3641(17) 0.905(2) 0.961(5) 1.000 0.038(10) . . H8B H Uiso 0.2994(17) 0.924(2) 0.915(6) 1.000 0.043(9) . . H8O H Uiso 0.375(2) 0.565(3) 0.992(8) 1.000 0.085(16) . . H14 H Uiso 0.1195(13) 0.3954(17) 1.034(5) 1.000 0.023(7) . . H15 H Uiso 0.0991(14) 0.254(2) 1.041(5) 1.000 0.033(8) . . H17 H Uiso 0.2667(15) 0.217(2) 0.796(6) 1.000 0.040(9) . . H18 H Uiso 0.2807(13) 0.3535(18) 0.807(5) 1.000 0.028(8) . . H21 H Uiso 0.2297(18) 0.824(2) 0.855(7) 1.000 0.063(13) . . H22 H Uiso 0.2046(14) 0.6777(18) 0.844(5) 1.000 0.039(9) . . H25 H Uiso 0.4034(17) 0.773(2) 0.983(6) 1.000 0.048(10) . . H2O H Uiso 0.532(2) -0.013(3) 0.165(9) 1.000 0.080(15) . . H3 H Uiso 0.5302(12) 0.1787(15) 0.247(4) 1.000 0.018(7) . . H3O H Uiso 0.3640(19) 0.059(2) 0.047(7) 1.000 0.066(12) . . H4 H Uiso 0.5098(14) 0.3163(18) 0.240(5) 1.000 0.027(8) . . H6 H Uiso 0.3336(15) 0.2681(19) 0.061(5) 1.000 0.037(9) . . H7A H Uiso 0.3743(19) 0.402(2) 0.070(7) 1.000 0.056(12) . . H7B H Uiso 0.4401(18) 0.427(2) 0.149(7) 1.000 0.059(11) . . H2N H Uiso 0.5136(16) 0.404(2) 0.636(6) 1.000 0.041(9) . . H3A H Uiso 0.444(2) 0.518(3) 0.562(8) 1.000 0.067(14) . . H3B H Uiso 0.455(2) 0.516(3) 0.765(8) 1.000 0.061(13) . . H10 H Uiso 0.3557(16) 0.256(2) 0.561(6) 1.000 0.045(10) . . H11 H Uiso 0.3726(15) 0.1103(19) 0.563(5) 1.000 0.036(9) . . H12 H Uiso 0.5384(14) 0.1312(19) 0.761(5) 1.000 0.037(9) . . H13 H Uiso 0.5234(17) 0.277(2) 0.757(6) 1.000 0.055(12) . . 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 O5 0.0224(9) 0.0301(9) 0.0585(13) 0.0021(10) -0.0023(9) -0.0058(7) O6 0.0289(9) 0.0258(8) 0.0545(13) -0.0004(9) -0.0057(9) 0.0066(7) O7 0.0267(9) 0.0234(8) 0.0581(13) 0.0021(9) -0.0053(10) -0.0015(6) O8 0.0189(8) 0.0377(10) 0.0500(12) 0.0037(9) -0.0015(8) 0.0039(7) N4 0.0277(10) 0.0240(9) 0.0357(11) 0.0019(10) -0.0044(10) -0.0022(8) N5 0.0255(10) 0.0194(9) 0.0444(13) -0.0008(10) -0.0035(10) -0.0021(7) N6 0.0374(12) 0.0191(9) 0.0531(16) 0.0003(11) -0.0005(12) -0.0024(8) N8 0.0322(12) 0.0285(10) 0.0434(13) -0.0019(11) -0.0028(11) -0.0085(9) C14 0.0232(11) 0.0276(11) 0.0359(13) 0.0001(11) -0.0039(10) 0.0011(9) C15 0.0193(10) 0.0312(12) 0.0293(12) 0.0001(10) -0.0024(10) -0.0034(9) C16 0.0217(10) 0.0226(10) 0.0260(11) -0.0005(10) -0.0038(9) -0.0023(8) C17 0.0224(11) 0.0260(12) 0.0286(13) -0.0001(10) -0.0003(9) -0.0011(9) C18 0.0225(11) 0.0280(12) 0.0355(13) 0.0031(11) 0.0002(10) -0.0028(9) C19 0.0237(11) 0.0256(10) 0.0302(12) -0.0003(10) -0.0040(10) -0.0019(9) C20 0.0273(12) 0.0299(11) 0.0264(11) -0.0001(10) 0.0013(11) -0.0061(9) C21 0.0224(11) 0.0260(12) 0.0314(14) -0.0020(10) -0.0002(10) -0.0007(9) C22 0.0215(11) 0.0279(11) 0.0304(14) -0.0013(10) -0.0008(10) -0.0005(9) C23 0.0189(10) 0.0278(11) 0.0281(11) -0.0010(10) 0.0021(9) -0.0002(8) C24 0.0196(10) 0.0330(12) 0.0276(12) 0.0001(10) 0.0012(9) 0.0034(9) C25 0.0201(10) 0.0341(13) 0.0299(12) 0.0008(10) -0.0001(10) -0.0066(9) C26 0.0258(12) 0.0248(11) 0.0348(13) -0.0024(11) 0.0001(10) 0.0015(9) O1 0.0271(9) 0.0266(8) 0.0612(14) -0.0047(9) -0.0017(9) -0.0039(7) O2 0.0239(8) 0.0254(8) 0.0598(13) -0.0002(10) -0.0036(9) 0.0007(7) O3 0.0204(8) 0.0310(9) 0.0481(11) -0.0015(9) -0.0054(8) -0.0062(7) N7 0.0322(12) 0.0246(10) 0.0500(15) -0.0014(11) -0.0047(12) 0.0018(9) C1 0.0236(11) 0.0281(12) 0.0336(12) -0.0005(11) 0.0009(10) -0.0026(9) C2 0.0226(10) 0.0245(11) 0.0284(12) -0.0006(10) 0.0001(10) -0.0027(9) C3 0.0196(10) 0.0294(11) 0.0267(12) -0.0013(10) -0.0012(10) -0.0020(9) C4 0.0230(11) 0.0290(12) 0.0304(13) -0.0030(11) -0.0014(10) -0.0052(9) C5 0.0257(12) 0.0262(11) 0.0274(12) 0.0004(10) 0.0023(10) 0.0001(9) C6 0.0189(10) 0.0293(12) 0.0308(13) 0.0020(10) 0.0001(9) -0.0018(9) C7 0.0197(10) 0.0303(12) 0.0281(11) -0.0026(10) 0.0013(9) -0.0063(9) O4 0.0232(9) 0.0333(9) 0.0568(14) 0.0059(10) 0.0062(10) 0.0040(7) N1 0.0254(10) 0.0268(9) 0.0345(12) 0.0007(10) 0.0007(9) -0.0008(8) N2 0.0220(10) 0.0247(10) 0.0611(17) 0.0004(12) 0.0050(11) 0.0016(8) N3 0.0300(11) 0.0260(11) 0.071(2) 0.0042(13) 0.0032(14) -0.0018(9) C8 0.0224(11) 0.0278(11) 0.0321(13) 0.0027(11) 0.0036(10) 0.0034(9) C9 0.0209(11) 0.0286(11) 0.0249(11) 0.0018(10) 0.0035(9) -0.0005(8) C10 0.0199(10) 0.0344(12) 0.0300(12) -0.0001(11) 0.0001(10) 0.0005(9) C11 0.0252(12) 0.0300(12) 0.0348(13) -0.0027(11) 0.0000(10) -0.0031(10) C12 0.0246(11) 0.0313(12) 0.0315(13) 0.0027(11) -0.0020(10) 0.0009(9) C13 0.0214(11) 0.0321(13) 0.0277(13) 0.0014(10) -0.0014(10) -0.0020(10) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; 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 O5 C19 1.228(3) . . yes O6 C26 1.254(3) . . yes O7 C26 1.298(3) . . yes O8 C24 1.365(3) . . yes O7 H7O 1.26(5) . . no O8 H8O 1.00(5) . . no O1 C1 1.242(3) . . yes O2 C1 1.302(3) . . yes O3 C7 1.366(3) . . yes O2 H2O 0.85(5) . . no O3 H3O 1.02(3) . . no O4 C8 1.220(3) . . yes N4 C14 1.336(3) . . yes N4 C18 1.336(3) . . yes N5 N6 1.429(3) . . yes N5 C19 1.334(3) . . yes N8 C20 1.363(3) . . yes N4 H7O 1.29(5) . . no N5 H5N 0.94(4) . . no N6 H6A 0.90(3) . . no N6 H6B 1.11(11) . . no N8 H8A 0.79(4) . . no N8 H8B 0.90(4) . . no N7 C5 1.378(3) . . yes N7 H7B 0.92(4) . . no N7 H7A 0.95(4) . . no N1 C12 1.339(3) . . yes N1 C11 1.343(3) . . yes N2 C8 1.337(3) . . yes N2 N3 1.410(3) . . yes N2 H2N 0.85(3) . . no N3 H3A 0.94(5) . . no N3 H3B 0.93(6) . . no C14 C15 1.396(4) . . no C15 C16 1.382(3) . . no C16 C17 1.387(3) . . no C16 C19 1.510(3) . . no C17 C18 1.390(4) . . no C20 C25 1.404(3) . . no C20 C21 1.411(3) . . no C21 C22 1.370(3) . . no C22 C23 1.401(3) . . no C23 C24 1.409(3) . . no C23 C26 1.471(3) . . no C24 C25 1.391(4) . . no C14 H14 1.00(3) . . no C15 H15 0.98(3) . . no C17 H17 0.95(3) . . no C18 H18 0.92(3) . . no C21 H21 0.97(4) . . no C22 H22 1.06(3) . . no C25 H25 0.91(4) . . no C1 C2 1.469(3) . . no C2 C7 1.406(3) . . no C2 C3 1.405(3) . . no C3 C4 1.382(4) . . no C4 C5 1.409(3) . . no C5 C6 1.397(3) . . no C6 C7 1.380(3) . . no C3 H3 0.93(3) . . no C4 H4 0.92(3) . . no C6 H6 1.04(3) . . no C8 C9 1.501(3) . . no C9 C10 1.390(3) . . no C9 C13 1.393(3) . . no C10 C11 1.384(4) . . no C12 C13 1.381(4) . . no C10 H10 0.97(4) . . no C11 H11 0.98(3) . . no C12 H12 1.05(3) . . no C13 H13 0.81(4) . . 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 C26 O7 H7O 116(2) . . . no C24 O8 H8O 101(3) . . . no C1 O2 H2O 118(3) . . . no C7 O3 H3O 108(2) . . . no C14 N4 C18 119.6(2) . . . yes N6 N5 C19 121.9(2) . . . yes C18 N4 H7O 120(2) . . . no C14 N4 H7O 121(2) . . . no C19 N5 H5N 122.8(19) . . . no N6 N5 H5N 115.2(19) . . . no H6A N6 H6B 118(5) . . . no N5 N6 H6B 126(5) . . . no N5 N6 H6A 110(2) . . . no H8A N8 H8B 124(3) . . . no C20 N8 H8B 115(2) . . . no C20 N8 H8A 117(2) . . . no C5 N7 H7A 112(2) . . . no H7A N7 H7B 118(3) . . . no C5 N7 H7B 120(2) . . . no C11 N1 C12 118.4(2) . . . yes N3 N2 C8 122.5(2) . . . yes C8 N2 H2N 124(2) . . . no N3 N2 H2N 113(2) . . . no N2 N3 H3B 102(3) . . . no N2 N3 H3A 104(3) . . . no H3A N3 H3B 107(4) . . . no N4 C14 C15 121.3(2) . . . yes C14 C15 C16 119.2(2) . . . no C15 C16 C19 118.3(2) . . . no C17 C16 C19 122.5(2) . . . no C15 C16 C17 119.1(2) . . . no C16 C17 C18 118.4(2) . . . no N4 C18 C17 122.3(2) . . . yes O5 C19 N5 123.9(2) . . . yes O5 C19 C16 120.5(2) . . . yes N5 C19 C16 115.6(2) . . . yes C21 C20 C25 118.4(2) . . . no N8 C20 C25 121.6(2) . . . yes N8 C20 C21 120.0(2) . . . yes C20 C21 C22 120.0(2) . . . no C21 C22 C23 122.3(2) . . . no C24 C23 C26 120.2(2) . . . no C22 C23 C24 117.8(2) . . . no C22 C23 C26 121.9(2) . . . no C23 C24 C25 120.2(2) . . . no O8 C24 C25 119.0(2) . . . yes O8 C24 C23 120.8(2) . . . yes C20 C25 C24 121.1(2) . . . no O6 C26 C23 121.3(2) . . . yes O7 C26 C23 116.3(2) . . . yes O6 C26 O7 122.4(2) . . . yes C15 C14 H14 121.5(17) . . . no N4 C14 H14 116.8(16) . . . no C14 C15 H15 118(2) . . . no C16 C15 H15 123(2) . . . no C18 C17 H17 118(2) . . . no C16 C17 H17 123(2) . . . no C17 C18 H18 117.8(18) . . . no N4 C18 H18 119.7(19) . . . no C20 C21 H21 117(2) . . . no C22 C21 H21 123(2) . . . no C21 C22 H22 123.3(17) . . . no C23 C22 H22 114.4(17) . . . no C20 C25 H25 116(2) . . . no C24 C25 H25 123(2) . . . no O1 C1 O2 123.1(2) . . . yes O1 C1 C2 121.6(2) . . . yes O2 C1 C2 115.3(2) . . . yes C1 C2 C3 121.3(2) . . . no C3 C2 C7 117.7(2) . . . no C1 C2 C7 121.0(2) . . . no C2 C3 C4 121.8(2) . . . no C3 C4 C5 119.6(2) . . . no C4 C5 C6 119.0(2) . . . no N7 C5 C4 120.2(2) . . . yes N7 C5 C6 120.8(2) . . . yes C5 C6 C7 120.9(2) . . . no O3 C7 C2 120.6(2) . . . yes C2 C7 C6 120.9(2) . . . no O3 C7 C6 118.5(2) . . . yes C4 C3 H3 121.4(16) . . . no C2 C3 H3 116.7(16) . . . no C3 C4 H4 119.1(19) . . . no C5 C4 H4 121.3(19) . . . no C5 C6 H6 121.3(18) . . . no C7 C6 H6 117.6(17) . . . no O4 C8 C9 121.2(2) . . . yes N2 C8 C9 116.0(2) . . . yes O4 C8 N2 122.8(2) . . . yes C8 C9 C13 123.6(2) . . . no C10 C9 C13 118.5(2) . . . no C8 C9 C10 117.9(2) . . . no C9 C10 C11 119.3(2) . . . no N1 C11 C10 122.1(2) . . . yes N1 C12 C13 123.2(2) . . . yes C9 C13 C12 118.5(2) . . . no C9 C10 H10 119(2) . . . no C11 C10 H10 122(2) . . . no N1 C11 H11 114.5(19) . . . no C10 C11 H11 123.4(19) . . . no N1 C12 H12 108.8(17) . . . no C13 C12 H12 128.1(18) . . . no C9 C13 H13 122(2) . . . no C12 C13 H13 119(2) . . . 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C18 N4 C14 C15 1.0(4) . . . . no C14 N4 C18 C17 -1.3(4) . . . . no N6 N5 C19 O5 1.2(5) . . . . no N6 N5 C19 C16 -177.8(3) . . . . no C11 N1 C12 C13 -0.8(4) . . . . no C12 N1 C11 C10 0.4(4) . . . . no N3 N2 C8 C9 -178.7(3) . . . . no N3 N2 C8 O4 1.0(5) . . . . no N4 C14 C15 C16 0.2(4) . . . . no C14 C15 C16 C17 -1.2(4) . . . . no C14 C15 C16 C19 -179.0(3) . . . . no C17 C16 C19 N5 27.4(4) . . . . no C19 C16 C17 C18 178.6(3) . . . . no C15 C16 C19 O5 26.2(4) . . . . no C17 C16 C19 O5 -151.6(3) . . . . no C15 C16 C17 C18 0.9(4) . . . . no C15 C16 C19 N5 -154.8(3) . . . . no C16 C17 C18 N4 0.4(4) . . . . no N8 C20 C25 C24 179.2(3) . . . . no C21 C20 C25 C24 -2.6(4) . . . . no C25 C20 C21 C22 3.1(4) . . . . no N8 C20 C21 C22 -178.7(3) . . . . no C20 C21 C22 C23 -0.3(4) . . . . no C21 C22 C23 C26 174.1(3) . . . . no C21 C22 C23 C24 -3.1(4) . . . . no C22 C23 C26 O6 -176.5(3) . . . . no C26 C23 C24 O8 6.1(4) . . . . no C26 C23 C24 C25 -173.7(3) . . . . no C22 C23 C24 O8 -176.6(3) . . . . no C22 C23 C24 C25 3.6(4) . . . . no C24 C23 C26 O7 -180.0(3) . . . . no C24 C23 C26 O6 0.7(4) . . . . no C22 C23 C26 O7 2.9(4) . . . . no O8 C24 C25 C20 179.4(3) . . . . no C23 C24 C25 C20 -0.8(4) . . . . no O1 C1 C2 C7 -9.4(4) . . . . no O2 C1 C2 C7 169.9(3) . . . . no O1 C1 C2 C3 171.4(3) . . . . no O2 C1 C2 C3 -9.3(4) . . . . no C7 C2 C3 C4 -0.7(4) . . . . no C3 C2 C7 O3 -180.0(3) . . . . no C3 C2 C7 C6 1.2(4) . . . . no C1 C2 C3 C4 178.6(3) . . . . no C1 C2 C7 O3 0.8(4) . . . . no C1 C2 C7 C6 -178.1(3) . . . . no C2 C3 C4 C5 -1.1(4) . . . . no C3 C4 C5 C6 2.3(4) . . . . no C3 C4 C5 N7 179.9(3) . . . . no C4 C5 C6 C7 -1.8(4) . . . . no N7 C5 C6 C7 -179.4(3) . . . . no C5 C6 C7 C2 0.0(4) . . . . no C5 C6 C7 O3 -178.8(3) . . . . no O4 C8 C9 C13 -154.3(3) . . . . no O4 C8 C9 C10 25.0(4) . . . . no N2 C8 C9 C13 25.4(4) . . . . no N2 C8 C9 C10 -155.3(3) . . . . no C13 C9 C10 C11 -0.4(4) . . . . no C8 C9 C10 C11 -179.8(3) . . . . no C8 C9 C13 C12 179.4(3) . . . . no C10 C9 C13 C12 0.0(4) . . . . no C9 C10 C11 N1 0.2(4) . . . . no N1 C12 C13 C9 0.6(4) . . . . 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 O1 C12 3.320(3) . 2_654 no O1 O3 2.586(3) . . no O1 N8 3.057(3) . 1_544 no O2 N1 2.575(3) . 2_654 no O2 C12 3.398(3) . 2_654 no O3 O1 2.586(3) . . no O3 N5 3.025(3) . 1_554 no O4 C18 3.351(3) . . no O4 N3 2.762(3) . . no O4 N6 3.007(3) . 3_554 no O4 O6 3.175(3) . . no O5 N3 3.043(4) . 3_545 no O5 O8 3.100(4) . 3_544 no O5 N6 2.780(3) . . no O6 N7 3.015(3) . 1_556 no O6 N6 3.260(4) . 3_555 no O6 O8 2.556(3) . . no O6 O4 3.175(3) . . no O8 N2 3.015(3) . 2_665 no O8 O6 2.556(3) . . no O8 O5 3.100(4) . 3_555 no O1 H12 2.58(3) . 2_654 no O1 H8A 2.35(3) . 1_544 no O1 H3O 1.69(4) . . no O2 H14 2.62(3) . 4_554 no O2 H3 2.42(3) . . no O3 H22 2.70(3) . 3_544 no O3 H5N 2.11(4) . 1_554 no O4 H18 2.43(3) . . no O4 H3B 2.67(5) . . no O4 H6A 2.16(3) . 3_554 no O4 H10 2.54(3) . . no O4 H7A 2.91(5) . 1_556 no O4 H3A 2.57(5) . . no O5 H15 2.64(3) . . no O5 H3A 2.20(5) . 3_545 no O5 H6A 2.70(3) . . no O6 H6B 2.56(12) . 3_555 no O6 H7A 2.22(4) . 1_556 no O6 H8O 1.60(5) . . no O7 H11 2.65(3) . 3_555 no O7 H22 2.38(3) . . no O8 H2N 2.22(4) . 2_665 no O8 H3B 2.64(5) . . no N1 C1 3.315(3) . 2_655 no N1 O2 2.575(3) . 2_655 no N2 O8 3.015(3) . 2_664 no N3 N7 3.095(3) . 2_665 no N3 O4 2.762(3) . . no N3 O5 3.043(4) . 3_554 no N5 O3 3.025(3) . 1_556 no N6 O4 3.007(3) . 3_545 no N6 O6 3.260(4) . 3_544 no N6 O5 2.780(3) . . no N6 N8 3.168(4) . 1_545 no N7 N3 3.095(3) . 2_664 no N7 O6 3.015(3) . 1_554 no N8 O1 3.057(3) . 1_566 no N8 C14 3.293(4) . 3_554 no N8 N6 3.168(4) . 1_565 no N1 H2O 1.73(5) . 2_655 no N2 H13 2.70(3) . . no N3 H7B 2.19(4) . 2_665 no N5 H17 2.69(3) . . no N6 H8B 2.28(4) . 1_545 no N6 H21 2.90(3) . 1_545 no N8 H6B 2.91(9) . 1_565 no C1 N1 3.315(3) . 2_654 no C2 C11 3.438(4) . . no C2 C12 3.327(4) . 1_554 no C3 C13 3.591(4) . 1_554 no C3 C12 3.560(4) . 1_554 no C3 C11 3.564(4) . . no C3 C15 3.570(4) . 4_554 no C4 C9 3.428(4) . . no C4 C10 3.520(4) . . no C4 C13 3.547(4) . 1_554 no C5 C9 3.542(4) . 1_554 no C5 C10 3.589(4) . . no C5 C13 3.575(4) . 1_554 no C6 C17 3.593(4) . 1_554 no C6 C9 3.437(4) . 1_554 no C6 C22 3.533(4) . 3_544 no C6 C10 3.587(4) . 1_554 no C7 C11 3.592(4) . 1_554 no C9 C5 3.542(4) . 1_556 no C9 C6 3.437(4) . 1_556 no C9 C4 3.428(4) . . no C10 C6 3.587(4) . 1_556 no C10 C5 3.589(4) . . no C10 C22 3.560(4) . 3_544 no C10 C4 3.520(4) . . no C11 C7 3.592(4) . 1_556 no C11 C2 3.438(4) . . no C11 C3 3.564(4) . . no C12 O1 3.320(3) . 2_655 no C12 C2 3.327(4) . 1_556 no C12 C3 3.560(4) . 1_556 no C12 O2 3.398(3) . 2_655 no C13 C4 3.547(4) . 1_556 no C13 C3 3.591(4) . 1_556 no C13 C5 3.575(4) . 1_556 no C14 N8 3.293(4) . 3_545 no C14 C20 3.352(4) . 3_545 no C15 C20 3.356(4) . 3_545 no C15 C25 3.448(4) . 3_545 no C15 C3 3.570(4) . 4_456 no C16 C24 3.531(4) . 3_544 no C16 C25 3.555(4) . 3_544 no C17 C20 3.494(4) . 3_544 no C17 C6 3.593(4) . 1_556 no C17 C22 3.551(4) . 3_544 no C17 C21 3.498(4) . 3_544 no C18 C21 3.544(4) . 3_544 no C18 C20 3.426(4) . 3_544 no C18 O4 3.351(3) . . no C19 C24 3.484(4) . 3_544 no C20 C15 3.356(4) . 3_554 no C20 C17 3.494(4) . 3_555 no C20 C14 3.352(4) . 3_554 no C20 C18 3.426(4) . 3_555 no C21 C18 3.544(4) . 3_555 no C21 C17 3.498(4) . 3_555 no C22 C10 3.560(4) . 3_555 no C22 C17 3.551(4) . 3_555 no C22 C6 3.533(4) . 3_555 no C24 C16 3.531(4) . 3_555 no C24 C19 3.484(4) . 3_555 no C25 C15 3.448(4) . 3_554 no C25 C16 3.555(4) . 3_555 no C1 H3O 2.30(4) . . no C3 H15 2.72(3) . 4_554 no C3 H25 3.07(4) . 2_664 no C4 H15 2.92(3) . 4_554 no C6 H22 2.85(3) . 3_544 no C7 H22 2.78(3) . 3_544 no C10 H22 2.99(3) . 3_544 no C11 H2O 2.70(5) . 2_655 no C11 H22 3.05(3) . 3_544 no C12 H25 2.89(4) . 2_664 no C12 H2O 2.66(5) . 2_655 no C13 H2N 2.66(3) . . no C13 H25 2.85(4) . 2_664 no C14 H12 2.87(3) . 4_455 no C15 H13 3.07(4) . 4_455 no C17 H6 2.67(3) . 1_556 no C17 H5N 2.61(3) . . no C18 H6 2.74(3) . 1_556 no C21 H10 2.93(4) . 3_555 no C21 H6B 3.05(8) . 1_565 no C21 H6 3.06(3) . 3_555 no C22 H17 3.10(4) . 3_555 no C22 H6 3.09(3) . 3_555 no C22 H10 2.80(4) . 3_555 no C25 H3 2.95(3) . 2_665 no C25 H15 3.10(4) . 3_554 no C26 H8O 2.18(4) . . no H2N C13 2.66(3) . . no H2N H13 2.28(5) . . no H2N O8 2.22(4) . 2_664 no H2O H12 2.58(6) . 2_654 no H2O C12 2.66(5) . 2_654 no H2O N1 1.73(5) . 2_654 no H2O C11 2.70(5) . 2_654 no H3 C25 2.95(3) . 2_664 no H3 H25 2.38(5) . 2_664 no H3 O2 2.42(3) . . no H3 H15 2.39(4) . 4_554 no H3A O5 2.20(5) . 3_554 no H3A O4 2.57(5) . . no H3B O4 2.67(5) . . no H3B H8O 2.53(7) . . no H3B O8 2.64(5) . . no H3O C1 2.30(4) . . no H3O H5N 2.57(6) . 1_554 no H3O O1 1.69(4) . . no H4 H7B 2.47(5) . . no H5N C17 2.61(3) . . no H5N O3 2.11(4) . 1_556 no H5N H17 2.22(5) . . no H5N H3O 2.57(6) . 1_556 no H6 C18 2.74(3) . 1_554 no H6 H18 2.59(5) . 1_554 no H6 H17 2.56(5) . 1_554 no H6 C22 3.09(3) . 3_544 no H6 C17 2.67(3) . 1_554 no H6 C21 3.06(3) . 3_544 no H6 H7A 2.38(5) . . no H6A O5 2.70(3) . . no H6A O4 2.16(3) . 3_545 no H6B H21 2.22(9) . 1_545 no H6B N8 2.91(9) . 1_545 no H6B C21 3.05(8) . 1_545 no H6B O6 2.56(12) . 3_544 no H6B H8B 2.09(10) . 1_545 no H7A O6 2.22(4) . 1_554 no H7A H6 2.38(5) . . no H7A O4 2.91(5) . 1_554 no H7B N3 2.19(4) . 2_664 no H7B H4 2.47(5) . . no H8A H25 2.35(5) . . no H8A O1 2.35(3) . 1_566 no H8B N6 2.28(4) . 1_565 no H8B H21 2.29(5) . . no H8B H6B 2.09(10) . 1_565 no H8O H3B 2.53(7) . . no H8O C26 2.18(4) . . no H8O O6 1.60(5) . . no H10 C22 2.80(4) . 3_544 no H10 H22 2.43(5) . 3_544 no H10 O4 2.54(3) . . no H10 C21 2.93(4) . 3_544 no H11 O7 2.65(3) . 3_544 no H11 H22 2.57(5) . 3_544 no H12 O1 2.58(3) . 2_655 no H12 H2O 2.58(6) . 2_655 no H12 C14 2.87(3) . 4_555 no H13 H2N 2.28(5) . . no H13 C15 3.07(4) . 4_555 no H13 N2 2.70(3) . . no H14 O2 2.62(3) . 4_456 no H15 O5 2.64(3) . . no H15 C25 3.10(4) . 3_545 no H15 C3 2.72(3) . 4_456 no H15 C4 2.92(3) . 4_456 no H15 H3 2.39(4) . 4_456 no H17 N5 2.69(3) . . no H17 H5N 2.22(5) . . no H17 H6 2.56(5) . 1_556 no H17 C22 3.10(4) . 3_544 no H18 O4 2.43(3) . . no H18 H6 2.59(5) . 1_556 no H21 N6 2.90(3) . 1_565 no H21 H6B 2.22(9) . 1_565 no H21 H8B 2.29(5) . . no H22 O7 2.38(3) . . no H22 O3 2.70(3) . 3_555 no H22 C6 2.85(3) . 3_555 no H22 C7 2.78(3) . 3_555 no H22 C10 2.99(3) . 3_555 no H22 C11 3.05(3) . 3_555 no H22 H10 2.43(5) . 3_555 no H22 H11 2.57(5) . 3_555 no H25 H8A 2.35(5) . . no H25 C3 3.07(4) . 2_665 no H25 C12 2.89(4) . 2_665 no H25 C13 2.85(4) . 2_665 no H25 H3 2.38(5) . 2_665 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # N2 H2N O8 0.85(3) 2.22(4) 3.015(3) 157(4) 2_664 yes O2 H2O N1 0.85(5) 1.73(5) 2.575(3) 172(5) 2_654 yes N3 H3A O5 0.94(5) 2.20(5) 3.043(4) 150(4) 3_554 yes O3 H3O O1 1.02(3) 1.69(4) 2.586(3) 145(3) . yes N5 H5N O3 0.94(4) 2.11(4) 3.025(3) 164(3) 1_556 yes N6 H6A O4 0.90(3) 2.16(3) 3.007(3) 158(3) 3_545 yes N6 H6B O6 1.11(11) 2.56(12) 3.260(4) 121(6) 3_544 yes N7 H7A O6 0.95(4) 2.22(4) 3.015(3) 141(3) 1_554 yes N7 H7B N3 0.92(4) 2.19(4) 3.095(3) 168(3) 2_664 yes O7 H7O N4 1.26(5) 1.29(5) 2.556(3) 175(7) . yes N8 H8A O1 0.79(4) 2.35(3) 3.057(3) 150(3) 1_566 yes N8 H8B N6 0.90(4) 2.28(4) 3.168(4) 173(3) 1_565 yes O8 H8O O6 1.00(5) 1.60(5) 2.556(3) 158(4) . yes C3 H3 O2 0.93(3) 2.42(3) 2.762(3) 101.3(18) . yes C12 H12 O1 1.05(3) 2.58(3) 3.320(3) 127(2) 2_655 yes C18 H18 O4 0.92(3) 2.43(3) 3.351(3) 173(3) . yes C22 H22 O7 1.06(3) 2.38(3) 2.789(3) 101(2) . yes # Loop Mechanism for Extra Tables(s) #loop_ #_publ_manuscript_incl_extra_item #'_geom_extra_tableA_col_1' #'_geom_extra_tableA_col_2' #'_geom_extra_tableA_col_3' #'_geom_extra_table_head_A' #'_geom_table_footnote_A' #'_geom_extra_tableB_col_1' #'_geom_extra_tableB_col_2' #'_geom_extra_tableB_col_3' #'_geom_extra_table_head_B' #'_geom_table_footnote_B' # #loop_ #_geom_extra_tableA_col_1 #_geom_extra_tableA_col_2 #_geom_extra_tableA_col_3 # ? ? ? # #loop_ #_geom_extra_tableB_col_1 #_geom_extra_tableB_col_2 #_geom_extra_tableB_col_3 # ? ? ? # #_geom_table_footnote_A #; # ? #; # #_geom_table_footnote_B #; # ? #; # #_geom_table_footnote_A #; # ? #; # #_geom_table_footnote_B #; # ? #; #===END # Attachment 'web_deposit_cif_file_1_PawelGrobelny_1289300182.cif' # CIF-file generated for datam in Pna21 #=============================================================================== data_datam2 _database_code_depnum_ccdc_archive 'CCDC 800271' #TrackingRef 'web_deposit_cif_file_1_PawelGrobelny_1289300182.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ; Pyrazinecarboxamide:4-aminosalicylic acid co-crystal hydrate ; _chemical_melting_point ? _chemical_formula_moiety 'C7 H7 N O3, C5 H5 N3 O, H2 O' _chemical_formula_structural ? _chemical_formula_sum 'C12 H14 N4 O5' _chemical_formula_iupac ? _chemical_formula_weight 294.27 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z _cell_length_a 6.7780(14) _cell_length_b 7.0380(14) _cell_length_c 15.050(3) _cell_angle_alpha 96.59(3) _cell_angle_beta 98.42(3) _cell_angle_gamma 105.27(3) _cell_volume 676.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150 _cell_measurement_reflns_used 1109 _cell_measurement_theta_min 2.8 _cell_measurement_theta_max 27.5 _cell_special_details ; ; _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.445 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 308 _exptl_absorpt_coefficient_mu 0.115 _exptl_crystal_density_meas_temp ? # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.9664 _exptl_absorpt_correction_T_max 0.9943 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 150(2) _diffrn_source_power 0.6 _diffrn_source_voltage 50.0 _diffrn_source_current 12.0 _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_source 'Sealed Tube' _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_measurement_specimen_support Fiber _diffrn_detector CCD _diffrn_measurement_device ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_detector_area_resol_mean 13.6612 _diffrn_measurement_method 'profile data from \w-scans' _diffrn_reflns_number 5940 _diffrn_reflns_av_R_equivalents 0.0921 _diffrn_reflns_av_sigmaI/netI 0.1044 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.39 _diffrn_reflns_theta_max 25.10 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 0.998 _reflns_number_total 2398 _reflns_number_gt 1358 _reflns_threshold_expression >2\s(I) _diffrn_measurement_details ; scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 10.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 0.0000 XTD: 49.4038 2theta: 29.5586 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 10.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 120.0000 XTD: 49.4038 2theta: 29.5586 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 10.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 240.0000 XTD: 49.4038 2theta: 29.5586 ; _diffrn_orient_matrix_UB_11 0.114326 _diffrn_orient_matrix_UB_12 0.036615 _diffrn_orient_matrix_UB_13 0.098996 _diffrn_orient_matrix_UB_21 0.112003 _diffrn_orient_matrix_UB_22 -0.094727 _diffrn_orient_matrix_UB_23 -0.027415 _diffrn_orient_matrix_UB_31 0.038559 _diffrn_orient_matrix_UB_32 0.039793 _diffrn_orient_matrix_UB_33 -0.039524 _diffrn_orient_matrix_type d*Trek _diffrn_reflns_reduction_process ; ; _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _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^ > 2\s(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^)+(0.0637P)^2^+0.2680P] 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 2398 _refine_ls_number_parameters 219 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.1284 _refine_ls_R_factor_gt 0.0630 _refine_ls_wR_factor_ref 0.1792 _refine_ls_wR_factor_gt 0.1318 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.242 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.063 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags O2 O Uani 0.6635(4) 0.3872(4) 0.39601(18) 1.000 0.0359(10) . . O3 O Uani 0.7902(5) 0.6749(4) 0.49239(17) 1.000 0.0374(10) . . O4 O Uani 0.6054(5) 0.3909(4) 0.22411(19) 1.000 0.0357(10) . . N4 N Uani 0.7403(7) 1.0157(6) 0.1202(3) 1.000 0.0385(14) . . C6 C Uani 0.7322(6) 0.6895(5) 0.3355(3) 1.000 0.0234(12) . . C7 C Uani 0.6707(6) 0.5934(5) 0.2448(3) 1.000 0.0247(12) . . C8 C Uani 0.6748(6) 0.7017(6) 0.1735(3) 1.000 0.0283(12) . . C9 C Uani 0.7399(6) 0.9095(6) 0.1906(3) 1.000 0.0271(12) . . C10 C Uani 0.8012(6) 1.0071(6) 0.2810(3) 1.000 0.0298(14) . . C11 C Uani 0.7986(6) 0.8989(6) 0.3511(3) 1.000 0.0273(12) . . C12 C Uani 0.7260(6) 0.5729(6) 0.4091(2) 1.000 0.0259(12) . . O1 O Uani 0.0431(5) 0.4149(4) 0.10908(18) 1.000 0.0392(10) . . N1 N Uani 0.2310(5) 0.5844(5) 0.3863(2) 1.000 0.0290(11) . . N2 N Uani 0.2484(5) 0.8646(5) 0.2669(2) 1.000 0.0275(11) . . N3 N Uani 0.1412(6) 0.7332(6) 0.0836(3) 1.000 0.0336(12) . . C1 C Uani 0.2877(6) 0.7816(6) 0.4166(3) 1.000 0.0298(14) . . C2 C Uani 0.2984(6) 0.9187(6) 0.3567(3) 1.000 0.0315(14) . . C3 C Uani 0.1868(6) 0.6684(6) 0.2377(3) 1.000 0.0268(12) . . C4 C Uani 0.1808(6) 0.5288(6) 0.2966(3) 1.000 0.0286(12) . . C5 C Uani 0.1192(6) 0.5963(6) 0.1372(3) 1.000 0.0273(12) . . O5 O Uani 0.2978(7) 0.1599(5) 0.0728(2) 1.000 0.0466(12) . . H3O H Uiso 0.77839 0.59556 0.53027 1.000 0.0561 . . H4A H Uiso 0.722(7) 0.949(6) 0.0645(17) 1.000 0.054(15) . . H4B H Uiso 0.804(6) 1.141(3) 0.131(3) 1.000 0.047(14) . . H4O H Uiso 0.604(8) 0.341(7) 0.271(2) 1.000 0.055(16) . . H8 H Uiso 0.63286 0.63383 0.11248 1.000 0.0342 . . H10 H Uiso 0.84461 1.14879 0.29373 1.000 0.0355 . . H11 H Uiso 0.84295 0.96748 0.41194 1.000 0.0327 . . H1 H Uiso 0.32123 0.82827 0.48026 1.000 0.0360 . . H2 H Uiso 0.34322 1.05691 0.38099 1.000 0.0377 . . H3A H Uiso 0.100(9) 0.703(9) 0.0240(15) 1.000 0.11(2) . . H3B H Uiso 0.211(10) 0.874(10) 0.103(4) 1.000 0.11(2) . . H4 H Uiso 0.13984 0.39075 0.27202 1.000 0.0342 . . H5A H Uiso 0.215(11) 0.226(11) 0.082(4) 1.000 0.11(3) . . H5B H Uiso 0.425(12) 0.218(12) 0.099(5) 1.000 0.14(3) . . 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 O2 0.052(2) 0.0232(17) 0.0291(17) 0.0060(12) 0.0040(14) 0.0058(15) O3 0.054(2) 0.0356(17) 0.0200(17) 0.0055(12) 0.0047(14) 0.0089(15) O4 0.054(2) 0.0222(16) 0.0253(18) 0.0036(13) -0.0005(15) 0.0057(14) N4 0.059(3) 0.028(2) 0.030(2) 0.0132(18) 0.009(2) 0.011(2) C6 0.021(2) 0.026(2) 0.025(2) 0.0046(16) 0.0055(16) 0.0089(18) C7 0.023(2) 0.023(2) 0.027(2) 0.0022(17) 0.0061(17) 0.0049(18) C8 0.031(2) 0.031(2) 0.024(2) 0.0044(17) 0.0032(18) 0.0116(19) C9 0.029(2) 0.029(2) 0.027(2) 0.0092(18) 0.0075(18) 0.0113(19) C10 0.034(2) 0.020(2) 0.035(3) 0.0044(18) 0.0071(19) 0.0066(19) C11 0.026(2) 0.027(2) 0.028(2) -0.0007(17) 0.0033(18) 0.0092(19) C12 0.031(2) 0.030(2) 0.018(2) 0.0043(17) 0.0047(17) 0.0109(19) O1 0.058(2) 0.0269(17) 0.0269(17) 0.0031(13) 0.0063(14) 0.0036(15) N1 0.0280(19) 0.039(2) 0.0221(19) 0.0060(15) 0.0083(14) 0.0106(17) N2 0.0281(19) 0.0301(19) 0.0212(19) -0.0011(14) 0.0016(14) 0.0066(16) N3 0.046(2) 0.030(2) 0.023(2) 0.0084(16) 0.0041(17) 0.0071(19) C1 0.030(2) 0.038(3) 0.021(2) 0.0031(18) 0.0019(17) 0.011(2) C2 0.030(2) 0.029(2) 0.032(3) 0.0015(18) 0.0016(19) 0.0059(19) C3 0.022(2) 0.030(2) 0.028(2) 0.0042(17) 0.0048(17) 0.0070(18) C4 0.030(2) 0.029(2) 0.025(2) 0.0037(17) 0.0031(17) 0.0067(19) C5 0.029(2) 0.026(2) 0.025(2) 0.0053(18) 0.0028(18) 0.0052(19) O5 0.049(2) 0.041(2) 0.043(2) -0.0016(15) -0.0041(18) 0.0117(19) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; 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 O2 C12 1.246(5) . . yes O3 C12 1.321(4) . . yes O4 C7 1.360(4) . . yes O3 H3O 0.8400 . . no O4 H4O 0.82(4) . . no O1 C5 1.241(5) . . yes O5 H5A 0.83(8) . . no O5 H5B 0.86(9) . . no N4 C9 1.365(6) . . yes N4 H4A 0.89(3) . . no N4 H4B 0.86(2) . . no N1 C1 1.343(5) . . yes N1 C4 1.329(5) . . yes N2 C3 1.333(5) . . yes N2 C2 1.329(5) . . yes N3 C5 1.319(6) . . yes N3 H3B 0.97(7) . . no N3 H3A 0.88(2) . . no C6 C11 1.404(5) . . no C6 C12 1.451(5) . . no C6 C7 1.403(6) . . no C7 C8 1.385(6) . . no C8 C9 1.393(6) . . no C9 C10 1.402(6) . . no C10 C11 1.370(6) . . no C8 H8 0.9500 . . no C10 H10 0.9500 . . no C11 H11 0.9500 . . no C1 C2 1.390(6) . . no C3 C4 1.394(6) . . no C3 C5 1.501(6) . . no C1 H1 0.9500 . . no C2 H2 0.9500 . . no C4 H4 0.9500 . . 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 C12 O3 H3O 109.00 . . . no C7 O4 H4O 110(3) . . . no H5A O5 H5B 114(7) . . . no C9 N4 H4B 119(3) . . . no H4A N4 H4B 119(4) . . . no C9 N4 H4A 117(3) . . . no C1 N1 C4 116.3(4) . . . yes C2 N2 C3 115.3(4) . . . yes C5 N3 H3B 125(4) . . . no C5 N3 H3A 122(4) . . . no H3A N3 H3B 112(5) . . . no C11 C6 C12 122.4(4) . . . no C7 C6 C11 117.5(4) . . . no C7 C6 C12 120.1(3) . . . no O4 C7 C8 117.9(4) . . . yes C6 C7 C8 121.1(3) . . . no O4 C7 C6 121.0(3) . . . yes C7 C8 C9 120.4(4) . . . no N4 C9 C8 120.3(4) . . . yes C8 C9 C10 119.0(4) . . . no N4 C9 C10 120.8(4) . . . yes C9 C10 C11 120.2(4) . . . no C6 C11 C10 121.8(4) . . . no O3 C12 C6 116.2(3) . . . yes O2 C12 C6 122.9(3) . . . yes O2 C12 O3 120.9(3) . . . yes C9 C8 H8 120.00 . . . no C7 C8 H8 120.00 . . . no C11 C10 H10 120.00 . . . no C9 C10 H10 120.00 . . . no C10 C11 H11 119.00 . . . no C6 C11 H11 119.00 . . . no N1 C1 C2 121.3(4) . . . yes N2 C2 C1 122.8(4) . . . yes C4 C3 C5 119.1(4) . . . no N2 C3 C4 122.7(4) . . . yes N2 C3 C5 118.2(4) . . . yes N1 C4 C3 121.5(4) . . . yes O1 C5 C3 119.3(4) . . . yes N3 C5 C3 117.0(4) . . . yes O1 C5 N3 123.7(4) . . . yes C2 C1 H1 119.00 . . . no N1 C1 H1 119.00 . . . no N2 C2 H2 119.00 . . . no C1 C2 H2 119.00 . . . no N1 C4 H4 119.00 . . . no C3 C4 H4 119.00 . . . 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N1 C4 C3 -0.1(6) . . . . no C4 N1 C1 C2 -1.8(6) . . . . no C3 N2 C2 C1 0.0(6) . . . . no C2 N2 C3 C5 177.4(4) . . . . no C2 N2 C3 C4 -1.9(6) . . . . no C11 C6 C7 O4 179.7(4) . . . . no C12 C6 C7 C8 179.8(4) . . . . no C11 C6 C7 C8 -0.3(6) . . . . no C11 C6 C12 O2 178.6(4) . . . . no C11 C6 C12 O3 -1.2(6) . . . . no C7 C6 C12 O3 178.8(4) . . . . no C7 C6 C12 O2 -1.5(6) . . . . no C7 C6 C11 C10 0.9(6) . . . . no C12 C6 C7 O4 -0.3(6) . . . . no C12 C6 C11 C10 -179.2(4) . . . . no C6 C7 C8 C9 -0.2(7) . . . . no O4 C7 C8 C9 179.9(4) . . . . no C7 C8 C9 C10 0.0(6) . . . . no C7 C8 C9 N4 -178.9(4) . . . . no C8 C9 C10 C11 0.6(6) . . . . no N4 C9 C10 C11 179.5(4) . . . . no C9 C10 C11 C6 -1.1(7) . . . . no N1 C1 C2 N2 1.9(7) . . . . no C5 C3 C4 N1 -177.3(4) . . . . no N2 C3 C5 O1 -173.3(4) . . . . no N2 C3 C4 N1 2.0(7) . . . . no C4 C3 C5 O1 6.0(6) . . . . no C4 C3 C5 N3 -175.4(4) . . . . no N2 C3 C5 N3 5.3(6) . . . . 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 O1 N3 2.935(5) . 2_565 no O1 N4 3.050(5) . 1_445 no O1 O5 2.861(5) . . no O2 C1 3.190(5) . 2_666 no O2 O4 2.564(4) . . no O2 N1 3.221(4) . 2_666 no O3 N1 2.718(4) . 2_666 no O4 O5 2.855(5) . . no O4 O2 2.564(4) . . no O5 N4 2.970(5) . 2_665 no O5 O1 2.861(5) . . no O5 O4 2.855(5) . . no O5 N3 2.942(5) . 1_545 no O1 H4B 2.26(3) . 1_445 no O1 H4 2.4800 . . no O1 H3A 2.07(3) . 2_565 no O1 H5A 2.03(8) . . no O2 H4O 1.84(3) . . no O2 H10 2.7800 . 1_545 no O2 H1 2.5400 . 2_666 no O2 H2 2.6900 . 1_545 no O3 H11 2.4800 . . no O4 H5B 2.13(7) . . no O4 H10 2.8300 . 1_545 no O4 H4B 2.85(4) . 1_545 no O5 H4A 2.09(3) . 2_665 no O5 H3B 2.07(7) . 1_545 no N1 N2 2.808(5) . . no N1 C12 3.346(6) . . no N1 O2 3.221(4) . 2_666 no N1 O3 2.718(4) . 2_666 no N1 C12 3.389(4) . 2_666 no N2 N3 2.733(5) . . no N2 N1 2.808(5) . . no N3 O5 2.942(5) . 1_565 no N3 N2 2.733(5) . . no N3 O1 2.935(5) . 2_565 no N4 O1 3.050(5) . 1_665 no N4 O5 2.970(5) . 2_665 no N1 H3O 1.8800 . 2_666 no N2 H3B 2.45(6) . . no N4 H5B 2.86(8) . 1_565 no C1 C6 3.593(6) . . no C1 O2 3.190(5) . 2_666 no C2 C11 3.342(6) . 1_455 no C2 C11 3.443(6) . . no C3 C8 3.537(6) . . no C3 C8 3.540(6) . 1_455 no C3 C7 3.417(6) . 1_455 no C3 C7 3.445(6) . . no C4 C7 3.447(6) . . no C4 C6 3.546(6) . . no C4 C7 3.590(6) . 1_455 no C5 C8 3.389(6) . 1_455 no C5 C8 3.587(6) . . no C6 C1 3.593(6) . . no C6 C4 3.546(6) . . no C7 C4 3.590(6) . 1_655 no C7 C3 3.445(6) . . no C7 C4 3.447(6) . . no C7 C3 3.417(6) . 1_655 no C8 C3 3.537(6) . . no C8 C3 3.540(6) . 1_655 no C8 C5 3.587(6) . . no C8 C5 3.389(6) . 1_655 no C11 C2 3.342(6) . 1_655 no C11 C2 3.443(6) . . no C12 N1 3.346(6) . . no C12 N1 3.389(4) . 2_666 no C1 H3O 2.8000 . 2_666 no C4 H10 3.0100 . 1_445 no C4 H3O 2.8400 . 2_666 no C5 H5A 2.91(7) . . no C5 H3A 2.94(4) . 2_565 no C10 H4O 3.00(5) . 1_565 no C10 H4 3.0800 . 1_665 no C12 H4O 2.38(4) . . no H1 O2 2.5400 . 2_666 no H2 O2 2.6900 . 1_565 no H3A C5 2.94(4) . 2_565 no H3A O1 2.07(3) . 2_565 no H3B H5A 2.53(10) . 1_565 no H3B H5B 2.49(11) . 1_565 no H3B N2 2.45(6) . . no H3B O5 2.07(7) . 1_565 no H3O C4 2.8400 . 2_666 no H3O N1 1.8800 . 2_666 no H3O C1 2.8000 . 2_666 no H4 H10 2.3500 . 1_445 no H4 C10 3.0800 . 1_445 no H4 O1 2.4800 . . no H4A O5 2.09(3) . 2_665 no H4A H8 2.3700 . . no H4A H5B 2.54(8) . 2_665 no H4A H5A 2.55(7) . 2_665 no H4B O1 2.26(3) . 1_665 no H4B H10 2.4200 . . no H4B O4 2.85(4) . 1_565 no H4O C12 2.38(4) . . no H4O H10 2.3900 . 1_545 no H4O O2 1.84(3) . . no H4O C10 3.00(5) . 1_545 no H5A H3B 2.53(10) . 1_545 no H5A H4A 2.55(7) . 2_665 no H5A O1 2.03(8) . . no H5A C5 2.91(7) . . no H5B N4 2.86(8) . 1_545 no H5B O4 2.13(7) . . no H5B H3B 2.49(11) . 1_545 no H5B H4A 2.54(8) . 2_665 no H8 H4A 2.3700 . . no H10 H4O 2.3900 . 1_565 no H10 O2 2.7800 . 1_565 no H10 O4 2.8300 . 1_565 no H10 C4 3.0100 . 1_665 no H10 H4 2.3500 . 1_665 no H10 H4B 2.4200 . . no H11 O3 2.4800 . . no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # N3 H3A O1 0.88(2) 2.07(3) 2.935(5) 168(6) 2_565 yes N3 H3B O5 0.97(7) 2.07(7) 2.942(5) 150(5) 1_565 yes O3 H3O N1 0.8400 1.8800 2.718(4) 176.00 2_666 yes N4 H4A O5 0.89(3) 2.09(3) 2.970(5) 170(4) 2_665 yes N4 H4B O1 0.86(2) 2.26(3) 3.050(5) 153(4) 1_665 yes O4 H4O O2 0.82(4) 1.84(3) 2.564(4) 146(4) . yes O5 H5A O1 0.83(8) 2.03(8) 2.861(5) 173(6) . yes O5 H5B O4 0.86(9) 2.13(7) 2.855(5) 141(7) . yes C1 H1 O2 0.9500 2.5400 3.190(5) 126.00 2_666 yes # Loop Mechanism for Extra Tables(s) #loop_ #_publ_manuscript_incl_extra_item #'_geom_extra_tableA_col_1' #'_geom_extra_tableA_col_2' #'_geom_extra_tableA_col_3' #'_geom_extra_table_head_A' #'_geom_table_footnote_A' #'_geom_extra_tableB_col_1' #'_geom_extra_tableB_col_2' #'_geom_extra_tableB_col_3' #'_geom_extra_table_head_B' #'_geom_table_footnote_B' # #loop_ #_geom_extra_tableA_col_1 #_geom_extra_tableA_col_2 #_geom_extra_tableA_col_3 # ? ? ? # #loop_ #_geom_extra_tableB_col_1 #_geom_extra_tableB_col_2 #_geom_extra_tableB_col_3 # ? ? ? # #_geom_table_footnote_A #; # ? #; # #_geom_table_footnote_B #; # ? #; # #_geom_table_footnote_A #; # ? #; # #_geom_table_footnote_B #; # ? #; #===END