#------------------------------------------------------------------------------ #$Date: 2026-06-05 20:28:33 +0100 (Fri, 05 Jun 2026) $ #$Revision: 306474 $ #$URL: svn://www.crystallography.net/cod/cif/7/06/43/7064339.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_7064339 loop_ _publ_author_name 'Borth, Ketlyn Wolfart' 'Leal, Let\'icia dos Santos' 'Teixeira, Ver\^onica de Carvalho' 'da Rocha, Grazielli' 'Sim\~oes, Tatiana Renata Gomes' _publ_section_title ; Hybrid azine--oxamic acid molecular design: synthesis, structure, and supramolecular implications ; _journal_issue 18 _journal_name_full 'New Journal of Chemistry' _journal_page_first 7619 _journal_page_last 7634 _journal_paper_doi 10.1039/D5NJ04656D _journal_volume 50 _journal_year 2026 _chemical_formula_moiety 'C22 H22 N4 O6' _chemical_formula_structural C22H22N4O6 _chemical_formula_sum 'C22 H22 N4 O6' _chemical_formula_weight 438.43 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary intrinsic-phasing _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2017/1 _audit_update_record ; 2025-08-08 deposited with the CCDC. 2026-03-05 downloaded from the CCDC. ; _cell_angle_alpha 114.5540(10) _cell_angle_beta 92.4900(10) _cell_angle_gamma 96.2670(10) _cell_formula_units_Z 2 _cell_length_a 7.4167(2) _cell_length_b 11.8025(3) _cell_length_c 13.2319(4) _cell_measurement_reflns_used 9956 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 74.2867 _cell_measurement_theta_min 4.2343 _cell_volume 1042.16(5) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX4 (2022)' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Mercury (Cambridge Crystallographic Data Centre, 2019)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008) and WINGX (Farrugia, 2012)' _computing_structure_refinement 'SHELXL-2017/1 (Sheldrick, 2017)' _computing_structure_solution 'SHELXT-2015 (Sheldrick 2015a)' _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 10.4167 _diffrn_measured_fraction_theta_full 0.988 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measurement_device_type 'Bruker D8 Venture/Photon 100 CMOS' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0375 _diffrn_reflns_av_unetI/netI 0.0212 _diffrn_reflns_Laue_measured_fraction_full 0.988 _diffrn_reflns_Laue_measured_fraction_max 0.989 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 28275 _diffrn_reflns_point_group_measured_fraction_full 0.988 _diffrn_reflns_point_group_measured_fraction_max 0.989 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 73.999 _diffrn_reflns_theta_min 4.234 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.865 _exptl_absorpt_correction_T_max 0.7538 _exptl_absorpt_correction_T_min 0.6564 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2012/1 - Bruker AXS area detector scaling and absorption correction ; _exptl_crystal_colour 'pale yellow' _exptl_crystal_density_diffrn 1.397 _exptl_crystal_description Parallelepiped _exptl_crystal_F_000 460 _exptl_crystal_size_max 0.336 _exptl_crystal_size_mid 0.111 _exptl_crystal_size_min 0.061 _refine_diff_density_max 0.240 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.042 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.115 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 377 _refine_ls_number_reflns 4192 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.115 _refine_ls_R_factor_all 0.0470 _refine_ls_R_factor_gt 0.0382 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0210P)^2^+0.6739P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0853 _refine_ls_wR_factor_ref 0.0905 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3631 _reflns_number_total 4192 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d5nj04656d2.cif _cod_data_source_block NN-Et2H2oba _cod_depositor_comments 'Adding full bibliography for 7064339--7064340.cif.' _cod_database_code 7064339 _shelx_shelxl_version_number 2017/1 _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_res_file ; TITL shelxt_a.res in P-1 shelx.res created by SHELXL-2017/1 at 09:15:54 on 08-Aug-2025 CELL 1.54184 7.4167 11.8025 13.2319 114.554 92.490 96.267 ZERR 2.00 0.0002 0.0003 0.0004 0.001 0.001 0.001 LATT 1 SFAC C H N O UNIT 44 44 8 12 MERG 2 OMIT 0.00 148.00 OMIT 4 -1 3 OMIT -4 -1 4 OMIT 3 3 7 OMIT -2 0 1 OMIT 0 -2 7 EQIV $3 -x+2, -y+2, -z+1 HTAB C4 O3_$3 HTAB N1 N2 EQIV $4 -x, -y+1, -z HTAB C15 O6_$4 HTAB N3 N4 FMAP 2 PLAN 20 ACTA BOND $H CONF LIST 4 L.S. 10 TEMP -173.35 WGHT 0.021000 0.673900 FVAR 0.94766 O1 4 0.600363 0.578790 0.263674 11.00000 0.03145 0.02201 = 0.02937 0.01202 0.00475 -0.00127 O2 4 0.741960 0.709525 0.197782 11.00000 0.03030 0.02724 = 0.02508 0.01447 0.00637 0.00106 O3 4 0.914426 0.852793 0.397645 11.00000 0.03882 0.02943 = 0.03306 0.01760 0.00214 -0.01052 O4 4 0.263400 0.725343 0.413329 11.00000 0.03451 0.02986 = 0.02213 0.01320 0.00222 -0.00102 O5 4 0.333885 0.791904 0.280998 11.00000 0.02667 0.02118 = 0.02394 0.01116 0.00371 -0.00113 O6 4 0.155846 0.578227 0.123835 11.00000 0.03495 0.03317 = 0.02037 0.01363 0.00346 -0.00483 N1 3 0.756628 0.729842 0.470970 11.00000 0.02086 0.01763 = 0.02655 0.01101 0.00330 -0.00075 N2 3 0.556789 0.555879 0.510687 11.00000 0.02040 0.01937 = 0.03022 0.01440 0.00548 0.00004 N3 3 0.051954 0.521218 0.260411 11.00000 0.02436 0.02288 = 0.01777 0.01027 0.00218 -0.00013 N4 3 -0.006456 0.488264 0.443567 11.00000 0.02465 0.02445 = 0.02062 0.01326 0.00700 0.00692 C1 1 0.704107 0.670614 0.275965 11.00000 0.02211 0.02093 = 0.02754 0.01256 0.00786 0.00547 C2 1 0.807381 0.763068 0.389214 11.00000 0.02094 0.01938 = 0.02833 0.01302 0.00549 0.00296 C3 1 0.804234 0.794476 0.586834 11.00000 0.01813 0.01931 = 0.02725 0.01255 0.00389 0.00466 C4 1 0.921719 0.908158 0.634521 11.00000 0.01964 0.02241 = 0.03222 0.01430 0.00267 0.00086 C5 1 0.956329 0.971437 0.749954 11.00000 0.02417 0.02207 = 0.03457 0.01087 -0.00053 -0.00011 C6 1 0.878886 0.922148 0.819299 11.00000 0.02704 0.02804 = 0.02752 0.01021 -0.00123 0.00284 C7 1 0.766564 0.807488 0.772193 11.00000 0.02340 0.02695 = 0.02831 0.01519 0.00432 0.00541 C8 1 0.726372 0.741907 0.656625 11.00000 0.01821 0.02093 = 0.02796 0.01337 0.00353 0.00436 C9 1 0.606478 0.622032 0.615245 11.00000 0.01976 0.02188 = 0.02802 0.01569 0.00658 0.00444 C10 1 0.641762 0.633874 0.087976 11.00000 0.03562 0.03039 = 0.02442 0.01058 0.00590 0.00279 C11 1 0.672684 0.706330 0.018482 11.00000 0.03882 0.04728 = 0.03401 0.02353 0.00896 0.00846 C12 1 0.255298 0.711736 0.318046 11.00000 0.02270 0.02359 = 0.02395 0.01283 0.00453 0.00359 C13 1 0.149028 0.595259 0.220574 11.00000 0.02179 0.02405 = 0.02126 0.01200 0.00337 0.00271 C14 1 -0.065545 0.407846 0.200292 11.00000 0.01932 0.02136 = 0.02391 0.01048 0.00405 0.00329 C15 1 -0.107094 0.358546 0.085053 11.00000 0.02443 0.02783 = 0.02439 0.01299 0.00405 0.00269 C16 1 -0.221964 0.245752 0.029334 11.00000 0.02830 0.03043 = 0.02496 0.00958 -0.00093 0.00059 C17 1 -0.298669 0.181019 0.087535 11.00000 0.02720 0.02584 = 0.03372 0.01022 0.00013 -0.00285 C18 1 -0.261177 0.230559 0.202147 11.00000 0.02358 0.02475 = 0.03262 0.01535 0.00463 0.00166 C19 1 -0.145015 0.343647 0.261057 11.00000 0.01885 0.02261 = 0.02537 0.01255 0.00469 0.00551 C20 1 -0.112956 0.386884 0.381416 11.00000 0.02067 0.02254 = 0.02618 0.01496 0.00835 0.00598 C21 1 0.425686 0.909437 0.369199 11.00000 0.02707 0.02083 = 0.02873 0.01021 0.00305 0.00135 C22 1 0.525046 0.984925 0.315802 11.00000 0.03216 0.02395 = 0.03762 0.01550 0.00655 0.00021 H1 2 0.563679 0.594760 0.671916 11.00000 0.02893 H2 2 0.713806 0.771508 0.820356 11.00000 0.02673 H3 2 0.905722 0.966525 0.900539 11.00000 0.02770 H4 2 1.035080 1.052047 0.781498 11.00000 0.02987 H5 2 0.976287 0.942245 0.587530 11.00000 0.02751 H6 2 0.674576 0.658274 0.449630 11.00000 0.03974 H7 2 0.509746 0.620264 0.096414 11.00000 0.02759 H8 2 0.682581 0.552381 0.057868 11.00000 0.03046 H9 2 0.621210 0.790199 0.054239 11.00000 0.04134 H10 2 0.602545 0.654075 -0.058995 11.00000 0.05208 H11 2 0.809084 0.723991 0.011648 11.00000 0.05156 H12 2 -0.173425 0.335952 0.415369 11.00000 0.02114 H13 2 -0.314836 0.187592 0.243965 11.00000 0.02491 H14 2 -0.381006 0.101645 0.047311 11.00000 0.03127 H15 2 -0.251414 0.212263 -0.052408 11.00000 0.02875 H16 2 -0.054091 0.402731 0.043418 11.00000 0.02732 H17 2 0.073237 0.546323 0.334067 11.00000 0.03483 H18 2 0.507946 0.886962 0.419110 11.00000 0.02231 H19 2 0.332616 0.952436 0.414980 11.00000 0.02409 H20 2 0.623451 0.937098 0.269831 11.00000 0.04546 H21 2 0.583492 1.069572 0.376892 11.00000 0.04373 H22 2 0.439049 1.004416 0.266626 11.00000 0.03293 HKLF 4 REM shelxt_a.res in P-1 REM R1 = 0.0382 for 3631 Fo > 4sig(Fo) and 0.0470 for all 4192 data REM 377 parameters refined using 0 restraints END WGHT 0.0210 0.6739 REM Highest difference peak 0.240, deepest hole -0.205, 1-sigma level 0.042 Q1 1 0.7350 0.7803 0.6245 11.00000 0.05 0.24 Q2 1 0.6624 0.6832 0.6211 11.00000 0.05 0.22 Q3 1 0.7707 0.7782 0.7161 11.00000 0.05 0.21 Q4 1 -0.1252 0.3841 0.2348 11.00000 0.05 0.21 Q5 1 0.9622 0.9318 0.6974 11.00000 0.05 0.20 Q6 1 -0.0023 0.5595 0.4367 11.00000 0.05 0.20 Q7 1 -0.1071 0.3897 0.1392 11.00000 0.05 0.20 Q8 1 0.8933 0.8420 0.6143 11.00000 0.05 0.20 Q9 1 0.8459 0.8617 0.7929 11.00000 0.05 0.20 Q10 1 -0.1911 0.2777 0.2236 11.00000 0.05 0.20 Q11 1 0.1865 0.6504 0.2734 11.00000 0.05 0.19 Q12 1 -0.2724 0.2208 0.0600 11.00000 0.05 0.18 Q13 1 0.9450 0.9336 0.7809 11.00000 0.05 0.18 Q14 1 -0.1348 0.3837 0.3182 11.00000 0.05 0.18 Q15 1 -0.0093 0.4555 0.2215 11.00000 0.05 0.18 Q16 1 0.0000 0.5000 0.5000 10.50000 0.05 0.18 Q17 1 -0.1380 0.2855 0.0616 11.00000 0.05 0.18 Q18 1 0.1925 0.6417 0.0917 11.00000 0.05 0.18 Q19 1 0.4725 0.9483 0.3349 11.00000 0.05 0.17 Q20 1 0.5677 0.5836 0.4531 11.00000 0.05 0.17 ; _shelx_res_checksum 65315 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' 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 O1 O 0.60036(15) 0.57879(9) 0.26367(9) 0.0276(2) Uani 1 1 d . . . . . O2 O 0.74196(14) 0.70952(10) 0.19778(8) 0.0265(2) Uani 1 1 d . . . . . O3 O 0.91443(16) 0.85279(10) 0.39764(9) 0.0336(3) Uani 1 1 d . . . . . O4 O 0.26340(15) 0.72534(10) 0.41333(8) 0.0286(2) Uani 1 1 d . . . . . O5 O 0.33388(14) 0.79190(9) 0.28100(8) 0.0237(2) Uani 1 1 d . . . . . O6 O 0.15585(15) 0.57823(10) 0.12383(8) 0.0295(2) Uani 1 1 d . . . . . N1 N 0.75663(16) 0.72984(11) 0.47097(10) 0.0214(2) Uani 1 1 d . . . . . N2 N 0.55679(16) 0.55588(11) 0.51069(10) 0.0221(3) Uani 1 1 d . . . . . N3 N 0.05195(16) 0.52122(11) 0.26041(10) 0.0214(3) Uani 1 1 d . . . . . N4 N -0.00646(16) 0.48826(11) 0.44357(9) 0.0215(3) Uani 1 1 d . . . . . C1 C 0.70411(19) 0.67061(13) 0.27597(12) 0.0224(3) Uani 1 1 d . . . . . C2 C 0.80738(19) 0.76307(13) 0.38921(12) 0.0218(3) Uani 1 1 d . . . . . C3 C 0.80423(18) 0.79448(12) 0.58683(12) 0.0204(3) Uani 1 1 d . . . . . C4 C 0.9217(2) 0.90816(13) 0.63452(13) 0.0240(3) Uani 1 1 d . . . . . C5 C 0.9563(2) 0.97144(14) 0.74995(13) 0.0277(3) Uani 1 1 d . . . . . C6 C 0.8789(2) 0.92215(15) 0.81930(13) 0.0283(3) Uani 1 1 d . . . . . C7 C 0.7666(2) 0.80749(14) 0.77219(13) 0.0248(3) Uani 1 1 d . . . . . C8 C 0.72637(19) 0.74191(13) 0.65662(12) 0.0212(3) Uani 1 1 d . . . . . C9 C 0.60648(19) 0.62203(13) 0.61525(12) 0.0212(3) Uani 1 1 d . . . . . C10 C 0.6418(2) 0.63387(16) 0.08798(13) 0.0305(3) Uani 1 1 d . . . . . C11 C 0.6727(3) 0.70633(19) 0.01848(15) 0.0375(4) Uani 1 1 d . . . . . C12 C 0.25530(19) 0.71174(13) 0.31805(12) 0.0224(3) Uani 1 1 d . . . . . C13 C 0.14903(19) 0.59526(13) 0.22057(12) 0.0215(3) Uani 1 1 d . . . . . C14 C -0.06555(19) 0.40785(13) 0.20029(12) 0.0211(3) Uani 1 1 d . . . . . C15 C -0.1071(2) 0.35855(14) 0.08505(12) 0.0249(3) Uani 1 1 d . . . . . C16 C -0.2220(2) 0.24575(15) 0.02933(13) 0.0290(3) Uani 1 1 d . . . . . C17 C -0.2987(2) 0.18102(15) 0.08753(14) 0.0304(3) Uani 1 1 d . . . . . C18 C -0.2612(2) 0.23056(14) 0.20215(13) 0.0260(3) Uani 1 1 d . . . . . C19 C -0.14501(19) 0.34365(13) 0.26106(12) 0.0212(3) Uani 1 1 d . . . . . C20 C -0.11296(19) 0.38688(13) 0.38142(12) 0.0211(3) Uani 1 1 d . . . . . C21 C 0.4257(2) 0.90944(14) 0.36920(13) 0.0258(3) Uani 1 1 d . . . . . C22 C 0.5250(2) 0.98492(15) 0.31580(15) 0.0306(3) Uani 1 1 d . . . . . H1 H 0.564(2) 0.5948(16) 0.6719(15) 0.029(4) Uiso 1 1 d . . . . . H2 H 0.714(2) 0.7715(16) 0.8204(14) 0.027(4) Uiso 1 1 d . . . . . H3 H 0.906(2) 0.9665(16) 0.9005(15) 0.028(4) Uiso 1 1 d . . . . . H4 H 1.035(2) 1.0520(17) 0.7815(14) 0.030(5) Uiso 1 1 d . . . . . H5 H 0.976(2) 0.9422(16) 0.5875(14) 0.028(4) Uiso 1 1 d . . . . . H6 H 0.675(3) 0.6583(19) 0.4496(16) 0.040(5) Uiso 1 1 d . . . . . H7 H 0.510(3) 0.6203(16) 0.0964(14) 0.028(4) Uiso 1 1 d . . . . . H8 H 0.683(2) 0.5524(17) 0.0579(15) 0.030(5) Uiso 1 1 d . . . . . H9 H 0.621(3) 0.7902(19) 0.0542(16) 0.041(5) Uiso 1 1 d . . . . . H10 H 0.603(3) 0.654(2) -0.0590(19) 0.052(6) Uiso 1 1 d . . . . . H11 H 0.809(3) 0.724(2) 0.0116(18) 0.052(6) Uiso 1 1 d . . . . . H12 H -0.173(2) 0.3360(15) 0.4154(13) 0.021(4) Uiso 1 1 d . . . . . H13 H -0.315(2) 0.1876(16) 0.2440(14) 0.025(4) Uiso 1 1 d . . . . . H14 H -0.381(2) 0.1016(17) 0.0473(15) 0.031(5) Uiso 1 1 d . . . . . H15 H -0.251(2) 0.2123(16) -0.0524(15) 0.029(4) Uiso 1 1 d . . . . . H16 H -0.054(2) 0.4027(16) 0.0434(14) 0.027(4) Uiso 1 1 d . . . . . H17 H 0.073(3) 0.5463(17) 0.3341(17) 0.035(5) Uiso 1 1 d . . . . . H18 H 0.508(2) 0.8870(15) 0.4191(14) 0.022(4) Uiso 1 1 d . . . . . H19 H 0.333(2) 0.9524(16) 0.4150(14) 0.024(4) Uiso 1 1 d . . . . . H20 H 0.623(3) 0.9371(19) 0.2698(17) 0.045(6) Uiso 1 1 d . . . . . H21 H 0.583(3) 1.070(2) 0.3769(17) 0.044(5) Uiso 1 1 d . . . . . H22 H 0.439(3) 1.0044(17) 0.2666(15) 0.033(5) 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 O1 0.0314(6) 0.0220(5) 0.0294(6) 0.0120(4) 0.0047(4) -0.0013(4) O2 0.0303(6) 0.0272(5) 0.0251(5) 0.0145(4) 0.0064(4) 0.0011(4) O3 0.0388(6) 0.0294(6) 0.0331(6) 0.0176(5) 0.0021(5) -0.0105(5) O4 0.0345(6) 0.0299(6) 0.0221(5) 0.0132(4) 0.0022(4) -0.0010(4) O5 0.0267(5) 0.0212(5) 0.0239(5) 0.0112(4) 0.0037(4) -0.0011(4) O6 0.0350(6) 0.0332(6) 0.0204(5) 0.0136(4) 0.0035(4) -0.0048(5) N1 0.0209(6) 0.0176(6) 0.0265(6) 0.0110(5) 0.0033(5) -0.0007(5) N2 0.0204(6) 0.0194(6) 0.0302(6) 0.0144(5) 0.0055(5) 0.0000(5) N3 0.0244(6) 0.0229(6) 0.0178(6) 0.0103(5) 0.0022(5) -0.0001(5) N4 0.0246(6) 0.0245(6) 0.0206(6) 0.0133(5) 0.0070(5) 0.0069(5) C1 0.0221(7) 0.0209(7) 0.0275(7) 0.0126(6) 0.0079(6) 0.0055(5) C2 0.0209(7) 0.0194(6) 0.0283(7) 0.0130(6) 0.0055(6) 0.0030(5) C3 0.0181(6) 0.0193(6) 0.0272(7) 0.0126(6) 0.0039(5) 0.0047(5) C4 0.0196(7) 0.0224(7) 0.0322(8) 0.0143(6) 0.0027(6) 0.0009(5) C5 0.0242(7) 0.0221(7) 0.0346(8) 0.0109(6) -0.0005(6) -0.0001(6) C6 0.0270(8) 0.0280(8) 0.0275(8) 0.0102(6) -0.0012(6) 0.0028(6) C7 0.0234(7) 0.0269(7) 0.0283(7) 0.0152(6) 0.0043(6) 0.0054(6) C8 0.0182(7) 0.0209(7) 0.0280(7) 0.0134(6) 0.0035(5) 0.0044(5) C9 0.0198(7) 0.0219(7) 0.0280(7) 0.0157(6) 0.0066(6) 0.0044(5) C10 0.0356(9) 0.0304(8) 0.0244(8) 0.0106(6) 0.0059(7) 0.0028(7) C11 0.0388(10) 0.0473(10) 0.0340(9) 0.0235(8) 0.0090(8) 0.0085(8) C12 0.0227(7) 0.0236(7) 0.0240(7) 0.0128(6) 0.0045(6) 0.0036(5) C13 0.0218(7) 0.0240(7) 0.0213(7) 0.0120(6) 0.0034(5) 0.0027(5) C14 0.0193(7) 0.0214(7) 0.0239(7) 0.0105(6) 0.0040(5) 0.0033(5) C15 0.0244(7) 0.0278(7) 0.0244(7) 0.0130(6) 0.0041(6) 0.0027(6) C16 0.0283(8) 0.0304(8) 0.0250(8) 0.0096(6) -0.0009(6) 0.0006(6) C17 0.0272(8) 0.0258(8) 0.0337(8) 0.0102(7) 0.0001(6) -0.0029(6) C18 0.0236(7) 0.0247(7) 0.0326(8) 0.0153(6) 0.0046(6) 0.0017(6) C19 0.0189(7) 0.0226(7) 0.0254(7) 0.0125(6) 0.0047(5) 0.0055(5) C20 0.0207(7) 0.0225(7) 0.0262(7) 0.0150(6) 0.0083(6) 0.0060(5) C21 0.0271(8) 0.0208(7) 0.0287(8) 0.0102(6) 0.0031(6) 0.0014(6) C22 0.0322(8) 0.0239(8) 0.0376(9) 0.0155(7) 0.0066(7) 0.0002(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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 _geom_angle_publ_flag C1 O2 C10 115.25(12) . . ? C12 O5 C21 113.96(11) . . ? C2 N1 C3 128.74(12) . . ? C2 N1 H6 116.5(12) . . ? C3 N1 H6 114.6(12) . . ? C9 N2 N2 112.95(14) . 2_666 ? C13 N3 C14 128.49(12) . . ? C13 N3 H17 114.1(12) . . ? C14 N3 H17 117.2(12) . . ? C20 N4 N4 113.17(14) . 2_566 ? O1 C1 O2 126.14(14) . . ? O1 C1 C2 123.59(13) . . ? O2 C1 C2 110.24(11) . . ? O3 C2 N1 128.01(14) . . ? O3 C2 C1 121.61(13) . . ? N1 C2 C1 110.36(12) . . ? C4 C3 N1 122.36(13) . . ? C4 C3 C8 119.64(13) . . ? N1 C3 C8 117.99(12) . . ? C5 C4 C3 119.92(14) . . ? C5 C4 H5 120.5(11) . . ? C3 C4 H5 119.6(11) . . ? C6 C5 C4 121.04(14) . . ? C6 C5 H4 120.4(10) . . ? C4 C5 H4 118.6(10) . . ? C7 C6 C5 119.21(14) . . ? C7 C6 H3 120.2(10) . . ? C5 C6 H3 120.6(10) . . ? C6 C7 C8 121.45(14) . . ? C6 C7 H2 119.6(10) . . ? C8 C7 H2 118.9(10) . . ? C7 C8 C3 118.69(13) . . ? C7 C8 C9 117.28(13) . . ? C3 C8 C9 124.03(13) . . ? N2 C9 C8 122.31(12) . . ? N2 C9 H1 121.4(10) . . ? C8 C9 H1 116.3(10) . . ? O2 C10 C11 107.28(13) . . ? O2 C10 H7 109.5(10) . . ? C11 C10 H7 110.0(10) . . ? O2 C10 H8 108.2(11) . . ? C11 C10 H8 114.5(11) . . ? H7 C10 H8 107.3(14) . . ? C10 C11 H9 109.8(11) . . ? C10 C11 H10 108.0(12) . . ? H9 C11 H10 108.1(16) . . ? C10 C11 H11 110.8(12) . . ? H9 C11 H11 109.3(16) . . ? H10 C11 H11 110.7(17) . . ? O4 C12 O5 126.15(13) . . ? O4 C12 C13 123.38(13) . . ? O5 C12 C13 110.47(11) . . ? O6 C13 N3 127.76(13) . . ? O6 C13 C12 122.20(12) . . ? N3 C13 C12 110.04(11) . . ? C15 C14 N3 122.39(13) . . ? C15 C14 C19 119.69(13) . . ? N3 C14 C19 117.91(12) . . ? C16 C15 C14 120.28(14) . . ? C16 C15 H16 119.8(10) . . ? C14 C15 H16 119.9(10) . . ? C15 C16 C17 120.63(14) . . ? C15 C16 H15 119.4(10) . . ? C17 C16 H15 119.9(10) . . ? C18 C17 C16 119.46(14) . . ? C18 C17 H14 120.6(11) . . ? C16 C17 H14 120.0(11) . . ? C17 C18 C19 121.49(14) . . ? C17 C18 H13 120.6(10) . . ? C19 C18 H13 118.0(10) . . ? C18 C19 C14 118.42(13) . . ? C18 C19 C20 117.13(13) . . ? C14 C19 C20 124.45(13) . . ? N4 C20 C19 122.45(12) . . ? N4 C20 H12 119.2(9) . . ? C19 C20 H12 118.3(9) . . ? O5 C21 C22 108.44(12) . . ? O5 C21 H18 107.5(9) . . ? C22 C21 H18 113.9(10) . . ? O5 C21 H19 107.5(10) . . ? C22 C21 H19 113.0(10) . . ? H18 C21 H19 106.3(13) . . ? C21 C22 H20 110.4(11) . . ? C21 C22 H21 108.9(11) . . ? H20 C22 H21 110.2(16) . . ? C21 C22 H22 111.3(11) . . ? H20 C22 H22 109.7(15) . . ? H21 C22 H22 106.3(15) . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.2057(17) . ? O2 C1 1.3236(17) . ? O2 C10 1.4641(19) . ? O3 C2 1.2144(17) . ? O4 C12 1.2008(17) . ? O5 C12 1.3286(16) . ? O5 C21 1.4592(17) . ? O6 C13 1.2147(17) . ? N1 C2 1.3496(18) . ? N1 C3 1.4068(18) . ? N1 H6 0.92(2) . ? N2 C9 1.2863(19) . ? N2 N2 1.399(2) 2_666 ? N3 C13 1.3558(18) . ? N3 C14 1.4083(18) . ? N3 H17 0.89(2) . ? N4 C20 1.2850(19) . ? N4 N4 1.398(2) 2_566 ? C1 C2 1.543(2) . ? C3 C4 1.397(2) . ? C3 C8 1.4197(19) . ? C4 C5 1.390(2) . ? C4 H5 0.952(18) . ? C5 C6 1.388(2) . ? C5 H4 0.974(18) . ? C6 C7 1.386(2) . ? C6 H3 0.980(18) . ? C7 C8 1.397(2) . ? C7 H2 0.975(18) . ? C8 C9 1.4599(19) . ? C9 H1 0.983(18) . ? C10 C11 1.503(2) . ? C10 H7 0.993(18) . ? C10 H8 0.965(18) . ? C11 H9 1.03(2) . ? C11 H10 1.03(2) . ? C11 H11 1.03(2) . ? C12 C13 1.541(2) . ? C14 C15 1.393(2) . ? C14 C19 1.4206(19) . ? C15 C16 1.387(2) . ? C15 H16 0.971(18) . ? C16 C17 1.390(2) . ? C16 H15 0.989(18) . ? C17 C18 1.382(2) . ? C17 H14 0.983(18) . ? C18 C19 1.399(2) . ? C18 H13 0.964(17) . ? C19 C20 1.455(2) . ? C20 H12 0.973(17) . ? C21 C22 1.504(2) . ? C21 H18 1.012(17) . ? C21 H19 0.979(18) . ? C22 H20 1.03(2) . ? C22 H21 1.02(2) . ? C22 H22 1.002(19) . ? 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 C4 H5 O3 0.952(18) 2.390(18) 3.1484(17) 136.4(14) 2_776 yes N1 H6 N2 0.92(2) 1.88(2) 2.6436(16) 140.0(17) . yes C15 H16 O6 0.971(18) 2.413(18) 3.1644(18) 133.9(13) 2_565 yes N3 H17 N4 0.89(2) 1.931(19) 2.6552(16) 136.9(17) . 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 C10 O2 C1 O1 2.0(2) . . . . ? C10 O2 C1 C2 -175.91(12) . . . . ? C3 N1 C2 O3 4.9(2) . . . . ? C3 N1 C2 C1 -173.52(12) . . . . ? O1 C1 C2 O3 178.06(14) . . . . ? O2 C1 C2 O3 -3.98(19) . . . . ? O1 C1 C2 N1 -3.44(19) . . . . ? O2 C1 C2 N1 174.52(12) . . . . ? C2 N1 C3 C4 -1.5(2) . . . . ? C2 N1 C3 C8 177.46(13) . . . . ? N1 C3 C4 C5 176.51(13) . . . . ? C8 C3 C4 C5 -2.4(2) . . . . ? C3 C4 C5 C6 1.4(2) . . . . ? C4 C5 C6 C7 0.5(2) . . . . ? C5 C6 C7 C8 -1.5(2) . . . . ? C6 C7 C8 C3 0.5(2) . . . . ? C6 C7 C8 C9 -179.91(13) . . . . ? C4 C3 C8 C7 1.5(2) . . . . ? N1 C3 C8 C7 -177.48(12) . . . . ? C4 C3 C8 C9 -178.12(13) . . . . ? N1 C3 C8 C9 2.9(2) . . . . ? N2 N2 C9 C8 179.52(14) 2_666 . . . ? C7 C8 C9 N2 178.02(13) . . . . ? C3 C8 C9 N2 -2.4(2) . . . . ? C1 O2 C10 C11 168.48(13) . . . . ? C21 O5 C12 O4 -4.6(2) . . . . ? C21 O5 C12 C13 175.48(11) . . . . ? C14 N3 C13 O6 -0.7(3) . . . . ? C14 N3 C13 C12 178.70(13) . . . . ? O4 C12 C13 O6 -173.33(15) . . . . ? O5 C12 C13 O6 6.64(19) . . . . ? O4 C12 C13 N3 7.2(2) . . . . ? O5 C12 C13 N3 -172.81(12) . . . . ? C13 N3 C14 C15 -4.1(2) . . . . ? C13 N3 C14 C19 176.73(13) . . . . ? N3 C14 C15 C16 179.25(14) . . . . ? C19 C14 C15 C16 -1.6(2) . . . . ? C14 C15 C16 C17 0.7(2) . . . . ? C15 C16 C17 C18 0.7(2) . . . . ? C16 C17 C18 C19 -1.1(2) . . . . ? C17 C18 C19 C14 0.2(2) . . . . ? C17 C18 C19 C20 -179.33(14) . . . . ? C15 C14 C19 C18 1.1(2) . . . . ? N3 C14 C19 C18 -179.65(13) . . . . ? C15 C14 C19 C20 -179.38(13) . . . . ? N3 C14 C19 C20 -0.2(2) . . . . ? N4 N4 C20 C19 -179.36(14) 2_566 . . . ? C18 C19 C20 N4 178.81(13) . . . . ? C14 C19 C20 N4 -0.7(2) . . . . ? C12 O5 C21 C22 173.96(13) . . . . ?