#------------------------------------------------------------------------------ #$Date: 2016-03-26 17:24:55 +0200 (Sat, 26 Mar 2016) $ #$Revision: 180392 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/20/61/7206132.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7206132 loop_ _publ_author_name 'Grobelny, Pawel' 'Mukherjee, Arijit' 'Desiraju, Gautam R.' _publ_section_title ; Drug-drug co-crystals: Temperature-dependent proton mobility in the molecular complex of isoniazid with 4-aminosalicylic acid ; _journal_issue 13 _journal_name_full CrystEngComm _journal_page_first 4358 _journal_paper_doi 10.1039/c0ce00842g _journal_volume 13 _journal_year 2011 _chemical_compound_source 'see text' _chemical_formula_moiety 'C7 H7 N O3, C6 H7 N3 O' _chemical_formula_sum 'C13 H14 N4 O4' _chemical_formula_weight 290.28 _chemical_name_common 'Isoniazid:4-aminosalicylic acid co-crystal' _chemical_name_systematic ? _space_group_IT_number 33 _symmetry_cell_setting orthorhombic _symmetry_Int_Tables_number 33 _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_space_group_name_H-M 'P n a 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 21.926(10) _cell_length_b 16.514(8) _cell_length_c 7.310(3) _cell_measurement_reflns_used 6328 _cell_measurement_temperature 240(2) _cell_measurement_theta_max 27.5 _cell_measurement_theta_min 1.9 _cell_volume 2647(2) _computing_publication_material 'PLATON (Spek, 2003)' _diffrn_ambient_temperature 240 _diffrn_detector CCD _diffrn_detector_area_resol_mean 13.6612 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _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_measurement_device ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_measurement_method 'profile data from \w-scans' _diffrn_measurement_specimen_support Fiber _diffrn_orient_matrix_type d*Trek _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_radiation_monochromator 'Graphite Monochromator' _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71075 _diffrn_reflns_av_R_equivalents 0.0522 _diffrn_reflns_av_sigmaI/netI 0.0240 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 27304 _diffrn_reflns_theta_full 27.49 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_min 1.54 _diffrn_source 'Sealed Tube' _diffrn_source_current 12.0 _diffrn_source_power 0.6 _diffrn_source_voltage 50.0 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.791 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_crystal_colour Yellow _exptl_crystal_density_diffrn 1.457 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_description Block _exptl_crystal_F_000 1216 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.160 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 492 _refine_ls_number_reflns 3277 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.160 _refine_ls_R_factor_all 0.0498 _refine_ls_R_factor_gt 0.0440 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0750P)^2^+0.2991P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1196 _refine_ls_wR_factor_ref 0.1305 _reflns_number_gt 3060 _reflns_number_total 3277 _reflns_threshold_expression >2\s(I) _cod_data_source_file c0ce00842g.txt _cod_data_source_block datam8 _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. '_exptl_absorpt_correction_type' value 'Multi-scan' changed to 'multi-scan' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 7206132 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 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) 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_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' 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_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_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 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 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