#------------------------------------------------------------------------------ #$Date: 2022-04-04 08:56:20 +0300 (Mon, 04 Apr 2022) $ #$Revision: 274292 $ #$URL: file:///home/coder/svn-repositories/cod/cif/3/00/02/3000220.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_3000220 loop_ _publ_author_name 'Gines M. Esteban-Parra' 'Eider San Sebasti\'an' 'Javier Cepeda' 'Cristina S\'anchez-Gonz\'alez' 'Lorenzo Rivas' 'Juan Llopis' 'Pilar Aranda' 'Miguel Quir\'os' 'Antonio Rodr\'iguez-Di\'eguez' _publ_section_title ; Anti-diabetic and anti-parasitic properties of a family of luminescent zinc coordination compounds based on the 7-amino-5-methyl-1,2,4-triazolo[1,5-a]pyrimidine ligand ; _journal_name_full 'Journal of Inorganic Biochemistry' _journal_page_first 111235 _journal_paper_doi 10.1016/j.jinorgbio.2020.111235 _journal_volume 212 _journal_year 2020 _chemical_formula_moiety 'C6 H7 N5, H2 O' _chemical_formula_sum 'C6 H9 N5 O' _chemical_formula_weight 167.18 _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_Hall '-P 2ac 2ab' _space_group_name_H-M_alt 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _atom_sites_solution_hydrogens difmap _audit_creation_method SHELXL-2018/3 _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 16 _cell_length_a 14.3058(9) _cell_length_b 7.1686(4) _cell_length_c 30.771(2) _cell_measurement_reflns_used 24331 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 28.401 _cell_measurement_theta_min 2.648 _cell_volume 3155.6(3) _computing_cell_refinement 'Bruker ApexII' _computing_data_collection 'Bruker ApexII' _computing_data_reduction 'Bruker ApexII' _computing_publication_material 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXL-2018/3 (Sheldrick, 2018)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Bruker D8 Venture' _diffrn_measurement_method 'Phi and Omega Scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_R_equivalents 0.0661 _diffrn_reflns_av_unetI/netI 0.0260 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 41 _diffrn_reflns_limit_l_min -41 _diffrn_reflns_number 75055 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_theta_full 25.240 _diffrn_reflns_theta_max 28.772 _diffrn_reflns_theta_min 2.648 _diffrn_source 'Fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_T_max 0.7458 _exptl_absorpt_correction_T_min 0.7180 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'Bruker SADABS (Bruker, 1999)' _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.408 _exptl_crystal_description Irregular _exptl_crystal_F_000 1408 _exptl_crystal_size_max 0.210 _exptl_crystal_size_mid 0.170 _exptl_crystal_size_min 0.140 _refine_diff_density_max 0.222 _refine_diff_density_min -0.317 _refine_diff_density_rms 0.070 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_hydrogen_treatment refxyz _refine_ls_matrix_type full _refine_ls_number_parameters 296 _refine_ls_number_reflns 4087 _refine_ls_number_restraints 4 _refine_ls_restrained_S_all 1.089 _refine_ls_R_factor_all 0.0603 _refine_ls_R_factor_gt 0.0453 _refine_ls_shift/su_max 0.020 _refine_ls_shift/su_mean 0.003 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+1.5000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1031 _refine_ls_wR_factor_ref 0.1099 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 3312 _reflns_number_total 4087 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file amtp.cif _cod_data_source_block amtp _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'Empirical' changed to 'empirical' according to the built-in table from CIF Core dictionary named 'cif_core.dic' version 2.4.5 from 2014-11-21. Automatic conversion script Id: cif_fix_values 6524 2018-11-02 12:15:13Z antanas Releasing structure 3000220 into public domain as published material. ; _cod_database_code 3000220 _cod_database_fobs_code 3000220 _shelx_shelxl_version_number 2018/3 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.978 _shelx_estimated_absorpt_t_max 0.986 _shelx_res_file ; TITL GGG in Pbca amtp.res created by SHELXL-2018/3 at 15:15:08 on 09-Jan-2019 CELL 0.71069 14.3058 7.1686 30.771 90 90 90 ZERR 16 0.0009 0.0004 0.002 0.00 0.00 0.00 LATT 1 SYMM 0.5-X,-Y,0.5+Z SYMM 0.5+X,0.5-Y,-Z SYMM -X,0.5+Y,0.5-Z SFAC C H N O UNIT 96 144 80 16 SIZE 0.21 0.17 0.14 TEMP -173.15 L.S. 4 PLAN 25 LIST 1 fmap 2 MERG 2 ACTA EADP O1W O1W' DFIX 0.84 0.01 O1W H11W O1W H12W O1W' H11' O1W' H12' WGHT 0.050000 1.500000 FVAR 0.08365 N1A 3 0.341075 0.697144 0.619229 11.00000 0.01309 0.02021 = 0.01786 0.00074 -0.00278 0.00008 C2A 1 0.424519 0.723893 0.601431 11.00000 0.01432 0.02658 = 0.02446 -0.00031 -0.00132 -0.00189 H2A 2 0.480485 0.690490 0.618487 11.00000 0.02723 N3A 3 0.427726 0.796584 0.560980 11.00000 0.01463 0.02540 = 0.02475 -0.00021 0.00248 -0.00421 C3AA 1 0.336722 0.818237 0.551124 11.00000 0.01623 0.01387 = 0.01710 -0.00238 0.00450 -0.00384 N4A 3 0.298252 0.882799 0.514527 11.00000 0.02131 0.01535 = 0.01388 -0.00094 0.00348 -0.00388 C5A 1 0.204203 0.886339 0.513620 11.00000 0.02299 0.01122 = 0.01363 -0.00220 0.00024 -0.00016 C6A 1 0.148286 0.830316 0.548319 11.00000 0.01594 0.01605 = 0.01420 -0.00062 -0.00034 0.00154 H6A 2 0.081742 0.833845 0.545481 11.00000 0.02051 C7A 1 0.188628 0.763122 0.586431 11.00000 0.01340 0.01225 = 0.01407 -0.00181 0.00204 -0.00048 N8A 3 0.284414 0.758888 0.585997 11.00000 0.01330 0.01340 = 0.01229 -0.00007 0.00026 -0.00120 C51A 1 0.159583 0.951422 0.472082 11.00000 0.03155 0.02271 = 0.01280 0.00154 -0.00169 -0.00107 H51D 2 0.105170 1.027583 0.476033 11.00000 0.05988 H51E 2 0.140646 0.848311 0.455170 11.00000 0.06848 H51F 2 0.201860 1.026540 0.455471 11.00000 0.05856 N71A 3 0.145520 0.703390 0.621864 11.00000 0.01207 0.02793 = 0.01465 0.00494 0.00154 0.00113 H71C 2 0.085285 0.715165 0.624361 11.00000 0.03633 H71D 2 0.179387 0.658683 0.643433 11.00000 0.03166 N1B 3 0.175080 -0.036544 0.205747 11.00000 0.01275 0.01910 = 0.01300 -0.00210 -0.00285 0.00097 C2B 1 0.086564 -0.025444 0.218355 11.00000 0.01166 0.02166 = 0.01745 -0.00254 -0.00271 0.00077 H2B 2 0.037813 -0.067647 0.198756 11.00000 0.02117 N3B 3 0.069918 0.046752 0.258275 11.00000 0.01057 0.01984 = 0.01537 -0.00154 -0.00077 0.00072 C3AB 1 0.156353 0.085356 0.272849 11.00000 0.00996 0.01385 = 0.01392 0.00180 0.00168 0.00154 N4B 3 0.182145 0.155947 0.311291 11.00000 0.01340 0.01507 = 0.01212 0.00002 -0.00012 0.00038 C5B 1 0.274896 0.173489 0.317457 11.00000 0.01474 0.01230 = 0.01450 0.00270 -0.00132 0.00009 C6B 1 0.341580 0.126102 0.286146 11.00000 0.00991 0.01517 = 0.01726 0.00195 -0.00120 -0.00017 H6B 2 0.405281 0.145504 0.292206 11.00000 0.02061 C7B 1 0.314764 0.051379 0.246328 11.00000 0.00927 0.01124 = 0.01631 0.00370 -0.00026 0.00112 N8B 3 0.219974 0.035578 0.241300 11.00000 0.01073 0.01404 = 0.01118 -0.00025 -0.00049 0.00064 C51B 1 0.305349 0.244313 0.361097 11.00000 0.01923 0.02259 = 0.01483 -0.00151 -0.00409 -0.00004 H51A 2 0.355219 0.339336 0.358587 11.00000 0.02941 H51B 2 0.333887 0.147025 0.377082 11.00000 0.04216 H51C 2 0.251771 0.294213 0.375738 11.00000 0.03755 N71B 3 0.369898 -0.007060 0.214225 11.00000 0.00891 0.02145 = 0.01664 -0.00143 0.00029 0.00060 H71A 2 0.345813 -0.048776 0.189199 11.00000 0.02665 H71B 2 0.431544 0.009639 0.217627 11.00000 0.02538 PART 1 O1W 4 0.455567 0.814337 0.365872 10.50000 0.01360 0.05738 = 0.02391 -0.01425 -0.00207 -0.00276 H11W 2 0.410760 0.763092 0.352663 10.50000 -1.20000 H12W 2 0.432160 0.859615 0.388799 10.50000 -1.20000 PART 2 O1W' 4 0.455349 0.714417 0.376919 10.50000 0.01360 0.05738 = 0.02391 -0.01425 -0.00207 -0.00276 H11' 2 0.412436 0.694067 0.358860 10.50000 -1.20000 H12' 2 0.437432 0.771905 0.399063 10.50000 -1.20000 PART 0 O2W 4 0.410393 0.964792 0.441607 11.00000 0.03039 0.04250 = 0.01858 -0.00319 0.00712 -0.01786 H2WA 2 0.458505 1.034933 0.448143 11.00000 0.05594 H2WB 2 0.379145 0.944362 0.466729 11.00000 0.04684 HKLF 4 REM GGG in Pbca REM wR2 = 0.1099, GooF = S = 1.089, Restrained GooF = 1.089 for all data REM R1 = 0.0453 for 3312 Fo > 4sig(Fo) and 0.0603 for all 4087 data REM 296 parameters refined using 4 restraints END WGHT 0.0514 1.5505 REM Highest difference peak 0.222, deepest hole -0.317, 1-sigma level 0.070 Q1 1 0.4501 0.8910 0.4502 11.00000 0.05 0.22 Q2 1 0.3072 0.1595 0.2983 11.00000 0.05 0.21 Q3 1 0.3344 0.1269 0.2590 11.00000 0.05 0.21 Q4 1 0.2663 0.4792 0.6376 11.00000 0.05 0.20 Q5 1 0.1978 0.0570 0.2584 11.00000 0.05 0.19 Q6 1 0.4725 1.0056 0.3597 11.00000 0.05 0.18 Q7 1 0.4602 0.4743 0.6099 11.00000 0.05 0.18 Q8 1 0.5004 0.6722 0.5384 11.00000 0.05 0.18 Q9 1 0.0325 0.5082 0.6292 11.00000 0.05 0.18 Q10 1 0.0889 0.9150 0.4719 11.00000 0.05 0.18 Q11 1 0.0010 -0.2234 0.2202 11.00000 0.05 0.17 Q12 1 0.4626 0.7839 0.5385 11.00000 0.05 0.17 Q13 1 0.1000 0.5289 0.5944 11.00000 0.05 0.17 Q14 1 0.5039 0.9918 0.3925 11.00000 0.05 0.17 Q15 1 0.1628 0.8123 0.5686 11.00000 0.05 0.17 Q16 1 0.0225 0.0923 0.2699 11.00000 0.05 0.17 Q17 1 0.3858 0.8566 0.5599 11.00000 0.05 0.16 Q18 1 0.4432 0.4839 0.3583 11.00000 0.05 0.16 Q19 1 0.5148 0.5075 0.6559 11.00000 0.05 0.16 Q20 1 0.2255 0.1042 0.1680 11.00000 0.05 0.16 Q21 1 0.4037 0.3259 0.2899 11.00000 0.05 0.16 Q22 1 0.4803 0.7147 0.3643 11.00000 0.05 0.16 Q23 1 0.1776 0.8367 0.5277 11.00000 0.05 0.15 Q24 1 0.5085 0.5247 0.3711 11.00000 0.05 0.15 Q25 1 0.4034 0.9325 0.4181 11.00000 0.05 0.15 ; _shelx_res_checksum 28997 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group N1A N 0.34108(7) 0.69714(16) 0.61923(4) 0.0171(2) Uani 1 1 d . . . . . C2A C 0.42452(9) 0.7239(2) 0.60143(5) 0.0218(3) Uani 1 1 d . . . . . H2A H 0.4805(13) 0.690(2) 0.6185(5) 0.027(4) Uiso 1 1 d . . . . . N3A N 0.42773(8) 0.79658(17) 0.56098(4) 0.0216(3) Uani 1 1 d . . . . . C3AA C 0.33672(9) 0.81824(18) 0.55112(4) 0.0157(3) Uani 1 1 d . . . . . N4A N 0.29825(8) 0.88280(15) 0.51453(3) 0.0168(2) Uani 1 1 d . . . . . C5A C 0.20420(9) 0.88634(17) 0.51362(4) 0.0159(3) Uani 1 1 d . . . . . C6A C 0.14829(9) 0.83032(18) 0.54832(4) 0.0154(3) Uani 1 1 d . . . . . H6A H 0.0817(11) 0.834(2) 0.5455(5) 0.021(4) Uiso 1 1 d . . . . . C7A C 0.18863(9) 0.76312(17) 0.58643(4) 0.0132(2) Uani 1 1 d . . . . . N8A N 0.28441(7) 0.75889(14) 0.58600(3) 0.0130(2) Uani 1 1 d . . . . . C51A C 0.15958(11) 0.9514(2) 0.47208(4) 0.0224(3) Uani 1 1 d . . . . . H51D H 0.1052(17) 1.028(3) 0.4760(7) 0.060(7) Uiso 1 1 d . . . . . H51E H 0.1406(17) 0.848(4) 0.4552(8) 0.068(7) Uiso 1 1 d . . . . . H51F H 0.2019(17) 1.027(3) 0.4555(7) 0.059(7) Uiso 1 1 d . . . . . N71A N 0.14552(8) 0.70339(17) 0.62186(4) 0.0182(2) Uani 1 1 d . . . . . H71C H 0.0853(15) 0.715(3) 0.6244(6) 0.036(5) Uiso 1 1 d . . . . . H71D H 0.1794(13) 0.659(3) 0.6434(6) 0.032(5) Uiso 1 1 d . . . . . N1B N 0.17508(7) -0.03654(15) 0.20575(3) 0.0149(2) Uani 1 1 d . . . . . C2B C 0.08656(9) -0.02544(19) 0.21835(4) 0.0169(3) Uani 1 1 d . . . . . H2B H 0.0378(12) -0.068(2) 0.1988(5) 0.021(4) Uiso 1 1 d . . . . . N3B N 0.06992(7) 0.04675(15) 0.25828(3) 0.0153(2) Uani 1 1 d . . . . . C3AB C 0.15635(8) 0.08536(17) 0.27285(4) 0.0126(2) Uani 1 1 d . . . . . N4B N 0.18214(7) 0.15595(14) 0.31129(3) 0.0135(2) Uani 1 1 d . . . . . C5B C 0.27490(8) 0.17349(17) 0.31746(4) 0.0138(3) Uani 1 1 d . . . . . C6B C 0.34158(8) 0.12610(17) 0.28615(4) 0.0141(2) Uani 1 1 d . . . . . H6B H 0.4053(12) 0.146(2) 0.2922(5) 0.021(4) Uiso 1 1 d . . . . . C7B C 0.31476(8) 0.05138(16) 0.24633(4) 0.0123(2) Uani 1 1 d . . . . . N8B N 0.21997(7) 0.03558(14) 0.24130(3) 0.0120(2) Uani 1 1 d . . . . . C51B C 0.30535(10) 0.2443(2) 0.36110(4) 0.0189(3) Uani 1 1 d . . . . . H51A H 0.3552(12) 0.339(3) 0.3586(6) 0.029(4) Uiso 1 1 d . . . . . H51B H 0.3339(14) 0.147(3) 0.3771(6) 0.042(5) Uiso 1 1 d . . . . . H51C H 0.2518(14) 0.294(3) 0.3757(6) 0.038(5) Uiso 1 1 d . . . . . N71B N 0.36990(7) -0.00706(16) 0.21422(4) 0.0157(2) Uani 1 1 d . . . . . H71A H 0.3458(12) -0.049(2) 0.1892(6) 0.027(4) Uiso 1 1 d . . . . . H71B H 0.4315(13) 0.010(2) 0.2176(5) 0.025(4) Uiso 1 1 d . . . . . O1W O 0.45557(18) 0.8143(4) 0.36587(9) 0.0316(5) Uani 0.5 1 d D . P A 1 H11W H 0.411(2) 0.763(5) 0.3527(13) 0.038 Uiso 0.5 1 d D U P B 1 H12W H 0.432(3) 0.860(5) 0.3888(8) 0.038 Uiso 0.5 1 d D U P C 1 O1W' O 0.45535(18) 0.7144(4) 0.37692(9) 0.0316(5) Uani 0.5 1 d D . P D 2 H11' H 0.412(2) 0.694(5) 0.3589(12) 0.038 Uiso 0.5 1 d D U P E 2 H12' H 0.437(3) 0.772(5) 0.3991(8) 0.038 Uiso 0.5 1 d D U P F 2 O2W O 0.41039(8) 0.96479(17) 0.44161(4) 0.0305(3) Uani 1 1 d . . . . . H2WA H 0.4585(17) 1.035(3) 0.4481(7) 0.056(7) Uiso 1 1 d . . . . . H2WB H 0.3791(15) 0.944(3) 0.4667(7) 0.047(6) Uiso 1 1 d . . . . . 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 N1A 0.0131(5) 0.0202(6) 0.0179(6) 0.0007(4) -0.0028(4) 0.0001(4) C2A 0.0143(6) 0.0266(7) 0.0245(7) -0.0003(6) -0.0013(5) -0.0019(5) N3A 0.0146(5) 0.0254(6) 0.0248(6) -0.0002(5) 0.0025(4) -0.0042(4) C3AA 0.0162(6) 0.0139(6) 0.0171(6) -0.0024(5) 0.0045(5) -0.0038(5) N4A 0.0213(5) 0.0153(5) 0.0139(5) -0.0009(4) 0.0035(4) -0.0039(4) C5A 0.0230(6) 0.0112(6) 0.0136(6) -0.0022(5) 0.0002(5) -0.0002(5) C6A 0.0159(6) 0.0160(6) 0.0142(6) -0.0006(5) -0.0003(5) 0.0015(5) C7A 0.0134(6) 0.0122(5) 0.0141(6) -0.0018(5) 0.0020(4) -0.0005(4) N8A 0.0133(5) 0.0134(5) 0.0123(5) -0.0001(4) 0.0003(4) -0.0012(4) C51A 0.0316(8) 0.0227(7) 0.0128(6) 0.0015(5) -0.0017(5) -0.0011(6) N71A 0.0121(5) 0.0279(6) 0.0147(5) 0.0049(5) 0.0015(4) 0.0011(4) N1B 0.0127(5) 0.0191(5) 0.0130(5) -0.0021(4) -0.0029(4) 0.0010(4) C2B 0.0117(6) 0.0217(6) 0.0174(6) -0.0025(5) -0.0027(5) 0.0008(5) N3B 0.0106(5) 0.0198(5) 0.0154(5) -0.0015(4) -0.0008(4) 0.0007(4) C3AB 0.0100(5) 0.0138(6) 0.0139(6) 0.0018(5) 0.0017(4) 0.0015(4) N4B 0.0134(5) 0.0151(5) 0.0121(5) 0.0000(4) -0.0001(4) 0.0004(4) C5B 0.0147(6) 0.0123(6) 0.0145(6) 0.0027(5) -0.0013(4) 0.0001(4) C6B 0.0099(5) 0.0152(6) 0.0173(6) 0.0019(5) -0.0012(4) -0.0002(5) C7B 0.0093(5) 0.0112(5) 0.0163(6) 0.0037(5) -0.0003(4) 0.0011(4) N8B 0.0107(5) 0.0140(5) 0.0112(5) -0.0003(4) -0.0005(4) 0.0006(4) C51B 0.0192(6) 0.0226(7) 0.0148(6) -0.0015(5) -0.0041(5) 0.0000(5) N71B 0.0089(5) 0.0214(6) 0.0166(5) -0.0014(4) 0.0003(4) 0.0006(4) O1W 0.0136(6) 0.0574(16) 0.0239(11) -0.0142(10) -0.0021(7) -0.0028(11) O1W' 0.0136(6) 0.0574(16) 0.0239(11) -0.0142(10) -0.0021(7) -0.0028(11) O2W 0.0304(6) 0.0425(7) 0.0186(5) -0.0032(5) 0.0071(4) -0.0179(5) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 C2A N1A N8A 100.16(11) . . N1A C2A N3A 117.82(12) . . C3AA N3A C2A 102.67(11) . . N4A C3AA N3A 128.93(12) . . N4A C3AA N8A 122.72(11) . . N3A C3AA N8A 108.35(11) . . C3AA N4A C5A 115.83(11) . . N4A C5A C6A 123.55(12) . . N4A C5A C51A 116.62(12) . . C6A C5A C51A 119.83(12) . . C7A C6A C5A 120.46(12) . . N71A C7A N8A 117.81(11) . . N71A C7A C6A 127.75(12) . . N8A C7A C6A 114.43(11) . . C7A N8A C3AA 122.99(11) . . C7A N8A N1A 126.01(10) . . C3AA N8A N1A 110.99(10) . . C2B N1B N8B 101.03(10) . . N1B C2B N3B 117.13(11) . . C3AB N3B C2B 102.68(10) . . N4B C3AB N3B 128.78(11) . . N4B C3AB N8B 122.59(11) . . N3B C3AB N8B 108.62(10) . . C3AB N4B C5B 115.57(11) . . N4B C5B C6B 123.56(11) . . N4B C5B C51B 116.36(11) . . C6B C5B C51B 120.07(11) . . C7B C6B C5B 120.83(11) . . N71B C7B N8B 118.46(11) . . N71B C7B C6B 127.67(11) . . N8B C7B C6B 113.85(11) . . C7B N8B N1B 125.85(10) . . C7B N8B C3AB 123.58(10) . . N1B N8B C3AB 110.53(10) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 N1A C2A 1.3273(17) . N1A N8A 1.3779(15) . C2A N3A 1.3502(19) . N3A C3AA 1.3457(17) . C3AA N4A 1.3361(17) . C3AA N8A 1.3757(16) . N4A C5A 1.3460(17) . C5A C6A 1.3933(18) . C5A C51A 1.5030(18) . C6A C7A 1.3930(18) . C7A N71A 1.3238(16) . C7A N8A 1.3707(16) . N1B C2B 1.3268(17) . N1B N8B 1.3699(14) . C2B N3B 1.3541(17) . N3B C3AB 1.3441(16) . C3AB N4B 1.3384(16) . C3AB N8B 1.3777(15) . N4B C5B 1.3463(16) . C5B C6B 1.3978(17) . C5B C51B 1.5003(18) . C6B C7B 1.3911(17) . C7B N71B 1.3317(16) . C7B N8B 1.3695(15) .