#------------------------------------------------------------------------------ #$Date: 2020-02-11 04:11:45 +0200 (Tue, 11 Feb 2020) $ #$Revision: 248019 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/72/1557295.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_1557295 loop_ _publ_author_name 'Schnell, Simon D.' 'Hoff, Lukas V.' 'Panchagnula, Advaita' 'Wurzenberger, Maximilian Hans Horst' 'Klapoetke, Thomas M.' 'Sieber, Simon' 'Linden, Anthony' 'Gademann, Karl' _publ_section_title ; 3-Bromotetrazine: Labelling of Macromolecules via Monosubstituted Bifunctional s-Tetrazines ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/C9SC06169J _journal_year 2020 _chemical_absolute_configuration syn _chemical_formula_moiety 'C17 H21 N5 O5' _chemical_formula_sum 'C17 H21 N5 O5' _chemical_formula_weight 375.39 _chemical_melting_point 393 _chemical_name_systematic Boc-Tyr(Tet)-OMe _space_group_crystal_system monoclinic _space_group_IT_number 5 _space_group_name_Hall 'C 2y' _space_group_name_H-M_alt 'C 1 2 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2019-10-11 deposited with the CCDC. 2020-02-10 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 94.704(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 32.663(2) _cell_length_b 5.1610(2) _cell_length_c 11.0162(6) _cell_measurement_reflns_used 3168 _cell_measurement_temperature 160(2) _cell_measurement_theta_max 71.0480 _cell_measurement_theta_min 4.0210 _cell_volume 1850.79(17) _computing_cell_refinement 'CrysAlisPro, Version 1.171.40.39a (Rigaku Oxford Diffraction, 2019)' _computing_data_collection 'CrysAlisPro, Version 1.171.40.39a (Rigaku Oxford Diffraction, 2019)' _computing_data_reduction 'CrysAlisPro, Version 1.171.40.39a (Rigaku Oxford Diffraction, 2019)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL-2018 and PLATON (Spek, 2015)' _computing_structure_refinement 'SHELXL-2018 (Sheldrick, 2015b)' _computing_structure_solution 'SHELXT-2018 (Sheldrick, 2015a)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 160(2) _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 10.3801 _diffrn_detector_type 'Atlas CCD area detector on \k goniostat' _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.988 _diffrn_measurement_device 'four-circle \k-geometry diffractometer' _diffrn_measurement_device_type 'Oxford Diffraction SuperNova, dual radiation diffractometer' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0635 _diffrn_reflns_av_unetI/netI 0.0452 _diffrn_reflns_Laue_measured_fraction_full 0.995 _diffrn_reflns_Laue_measured_fraction_max 0.988 _diffrn_reflns_limit_h_max 40 _diffrn_reflns_limit_h_min -40 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 13382 _diffrn_reflns_point_group_measured_fraction_full 0.984 _diffrn_reflns_point_group_measured_fraction_max 0.967 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 73.150 _diffrn_reflns_theta_min 2.715 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray source' _exptl_absorpt_coefficient_mu 0.849 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.56496 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Empirical absorption correction using spherical harmonics, implemented in the SCALE3 ABSPACK scaling algorithm. CrysAlisPro, Version 1.171.40.39a (Rigaku Oxford Diffraction, 2019) ; _exptl_crystal_colour pink _exptl_crystal_density_diffrn 1.347 _exptl_crystal_description needle _exptl_crystal_F_000 792 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: diethyl ether' _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _refine_diff_density_max 0.288 _refine_diff_density_min -0.175 _refine_diff_density_rms 0.041 _refine_ls_abs_structure_details ; Flack x determined using 1051 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.0(3) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 252 _refine_ls_number_reflns 3606 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.039 _refine_ls_R_factor_all 0.0664 _refine_ls_R_factor_gt 0.0541 _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^)+(0.0850P)^2^+0.5336P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1433 _refine_ls_wR_factor_ref 0.1556 _reflns_Friedel_coverage 0.754 _reflns_Friedel_fraction_full 0.971 _reflns_Friedel_fraction_max 0.942 _reflns_number_gt 2965 _reflns_number_total 3606 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9sc06169j2.cif _cod_data_source_block 23 _cod_depositor_comments ; The following automatic conversions were performed: data item '_atom_sites_solution_hydrogens' value 'geom & difmap' was changed to 'mixed'. Automatic conversion script Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas ; _cod_original_sg_symbol_H-M 'C 2' _cod_database_code 1557295 _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. ; _oxdiff_exptl_absorpt_empirical_full_min 0.663 _oxdiff_exptl_absorpt_empirical_full_max 1.650 _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _shelx_res_file ; TITL gd1902a_cu_a.res in C2 x.res created by SHELXL-2018/3 at 09:55:07 on 07-Mar-2019 REM Old TITL GD1902a_Cu in C8 REM SHELXT solution in C2: R1 0.169, Rweak 0.046, Alpha 0.004 REM 0.000 for 0 systematic absences, Orientation as input REM Flack x = 0.429 ( 0.271 ) from 1113 Parsons' quotients REM Formula found by SHELXT: C16 N2 O4 CELL 1.54184 32.663 5.161 11.0162 90 94.704 90 ZERR 4 0.002 0.0002 0.0006 0 0.005 0 LATT -7 SYMM -X,+Y,-Z SFAC C H N O UNIT 68 84 20 20 L.S. 8 PLAN 12 TEMP -113 BOND $H CONF EQIV $1 x, y-1, z HTAB N5 O4_$1 fmap 2 acta DFIX 0.88 0.01 N5 H5 WGHT 0.085000 0.533600 FVAR 5.07317 O1 4 0.270768 0.684869 0.181206 11.00000 0.07071 0.05137 = 0.04821 0.01161 0.00006 -0.01078 O2 4 0.404567 0.523896 0.881113 11.00000 0.14261 0.14836 = 0.05104 -0.03427 -0.01618 0.07458 O3 4 0.426350 0.185206 0.787664 11.00000 0.14490 0.07123 = 0.04043 0.00542 0.00025 0.03135 O4 4 0.412533 0.870499 0.507012 11.00000 0.06628 0.03141 = 0.04326 -0.00058 0.00842 0.00149 O5 4 0.438279 0.550302 0.393693 11.00000 0.09732 0.03218 = 0.04406 0.00056 0.02832 0.00155 N1 3 0.220593 0.380948 0.198186 11.00000 0.06400 0.06652 = 0.04291 0.01091 0.00327 -0.01160 N2 3 0.186917 0.269966 0.146205 11.00000 0.07670 0.09801 = 0.04842 0.02388 -0.00428 -0.02905 N3 3 0.185955 0.566830 -0.016952 11.00000 0.06677 0.07227 = 0.04519 0.01462 0.00343 0.00696 N4 3 0.219507 0.677959 0.033281 11.00000 0.07045 0.05270 = 0.04369 0.01195 0.00346 0.00683 N5 3 0.415162 0.451418 0.570412 11.00000 0.05844 0.03115 = 0.03793 -0.00105 0.01138 0.00173 H5 2 0.421554 0.292103 0.553321 11.00000 0.06500 C1 1 0.235927 0.573009 0.136783 11.00000 0.06170 0.04352 = 0.03341 0.00748 0.00968 0.00289 C2 1 0.171894 0.365609 0.040359 11.00000 0.06880 0.09025 = 0.04545 0.01835 -0.00478 -0.01703 AFIX 43 H2 2 0.148560 0.280398 0.001690 11.00000 -1.20000 AFIX 0 C3 1 0.288760 0.595768 0.294855 11.00000 0.05913 0.03929 = 0.04225 0.00492 0.00344 -0.00502 C4 1 0.314126 0.383190 0.297946 11.00000 0.06815 0.04290 = 0.03885 -0.00791 0.00872 0.00149 AFIX 43 H4 2 0.319026 0.292976 0.225375 11.00000 -1.20000 AFIX 0 C5 1 0.332422 0.303680 0.410050 11.00000 0.05905 0.03734 = 0.04459 -0.00585 0.00882 0.00053 AFIX 43 H5A 2 0.349944 0.156481 0.414130 11.00000 -1.20000 AFIX 0 C6 1 0.325461 0.436893 0.517073 11.00000 0.05101 0.03473 = 0.04225 -0.00605 0.01098 -0.00699 C7 1 0.300100 0.651846 0.508764 11.00000 0.05529 0.04107 = 0.04318 -0.01029 0.00981 -0.00282 AFIX 43 H7 2 0.295316 0.745518 0.580478 11.00000 -1.20000 AFIX 0 C8 1 0.281617 0.732573 0.397991 11.00000 0.05639 0.03784 = 0.05373 -0.00757 0.01028 -0.00086 AFIX 43 H8 2 0.264232 0.880413 0.393168 11.00000 -1.20000 AFIX 0 C9 1 0.346308 0.350094 0.636536 11.00000 0.05903 0.03900 = 0.03791 -0.00139 0.01048 -0.00389 AFIX 23 H91 2 0.351111 0.160853 0.633891 11.00000 -1.20000 H92 2 0.328126 0.385238 0.702247 11.00000 -1.20000 AFIX 0 C10 1 0.387676 0.490274 0.665518 11.00000 0.05705 0.03516 = 0.03363 -0.00135 0.00841 0.00279 AFIX 13 H10 2 0.381869 0.680114 0.670072 11.00000 -1.20000 AFIX 0 C11 1 0.406832 0.405246 0.789645 11.00000 0.05895 0.05533 = 0.03862 -0.00548 0.00953 0.00165 C12 1 0.444754 0.092879 0.903947 11.00000 0.12335 0.10989 = 0.04549 0.02016 0.00543 0.03739 AFIX 137 H121 2 0.456661 -0.079166 0.893460 11.00000 -1.50000 H122 2 0.423667 0.082243 0.962115 11.00000 -1.50000 H123 2 0.466371 0.213170 0.934848 11.00000 -1.50000 AFIX 0 C13 1 0.420976 0.644075 0.490881 11.00000 0.05239 0.03292 = 0.03966 -0.00114 0.00647 -0.00174 C14 1 0.447435 0.721977 0.292955 11.00000 0.09668 0.03682 = 0.04479 0.00351 0.02368 -0.00043 C15 1 0.409081 0.864914 0.241970 11.00000 0.08326 0.09045 = 0.05031 0.02072 -0.00067 -0.01063 AFIX 137 H151 2 0.386449 0.741325 0.227061 11.00000 -1.50000 H152 2 0.414499 0.949725 0.165320 11.00000 -1.50000 H153 2 0.401586 0.995785 0.300679 11.00000 -1.50000 AFIX 0 C16 1 0.462993 0.539299 0.201426 11.00000 0.23866 0.04868 = 0.07367 -0.00314 0.09084 -0.00278 AFIX 137 H161 2 0.485400 0.434708 0.240469 11.00000 -1.50000 H162 2 0.473122 0.638587 0.134217 11.00000 -1.50000 H163 2 0.440626 0.425195 0.169764 11.00000 -1.50000 AFIX 0 C17 1 0.481430 0.909831 0.338383 11.00000 0.06965 0.06581 = 0.07128 0.02004 0.01784 -0.00379 AFIX 137 H171 2 0.471230 1.025466 0.399703 11.00000 -1.50000 H172 2 0.489824 1.012686 0.269878 11.00000 -1.50000 H173 2 0.505052 0.811888 0.374719 11.00000 -1.50000 AFIX 0 HKLF 4 REM gd1902a_cu_a.res in C2 REM wR2 = 0.1556, GooF = S = 1.039, Restrained GooF = 1.039 for all data REM R1 = 0.0541 for 2965 Fo > 4sig(Fo) and 0.0664 for all 3606 data REM 252 parameters refined using 2 restraints END WGHT 0.0850 0.5339 REM Highest difference peak 0.288, deepest hole -0.175, 1-sigma level 0.041 Q1 1 0.3865 0.3486 0.8603 11.00000 0.05 0.29 Q2 1 0.4395 0.3638 0.7837 11.00000 0.05 0.26 Q3 1 0.4085 0.5435 0.3834 11.00000 0.05 0.20 Q4 1 0.4178 0.5034 0.1638 11.00000 0.05 0.20 Q5 1 0.2865 0.4164 0.3029 11.00000 0.05 0.19 Q6 1 0.2992 0.4605 0.5168 11.00000 0.05 0.18 Q7 1 0.3983 0.2265 0.8122 11.00000 0.05 0.18 Q8 1 0.3293 0.6296 0.5085 11.00000 0.05 0.17 Q9 1 0.4135 0.7264 0.2751 11.00000 0.05 0.15 Q10 1 0.2992 0.6857 0.1817 11.00000 0.05 0.15 Q11 1 0.4456 0.4668 0.5846 11.00000 0.05 0.15 Q12 1 0.3175 0.5933 0.2999 11.00000 0.05 0.15 ; _shelx_res_checksum 40968 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -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 O1 O 0.27077(10) 0.6849(6) 0.1812(3) 0.0570(8) Uani 1 1 d . . O2 O 0.40457(18) 0.5239(12) 0.8811(4) 0.115(2) Uani 1 1 d . . O3 O 0.42635(16) 0.1852(8) 0.7877(3) 0.0859(13) Uani 1 1 d . . O4 O 0.41253(9) 0.8705(5) 0.5070(2) 0.0468(6) Uani 1 1 d . . O5 O 0.43828(11) 0.5503(5) 0.3937(3) 0.0566(8) Uani 1 1 d . . N1 N 0.22059(12) 0.3809(9) 0.1982(3) 0.0579(9) Uani 1 1 d . . N2 N 0.18692(14) 0.2700(11) 0.1462(4) 0.0749(14) Uani 1 1 d . . N3 N 0.18596(13) 0.5668(9) -0.0170(3) 0.0615(10) Uani 1 1 d . . N4 N 0.21951(12) 0.6780(8) 0.0333(3) 0.0557(9) Uani 1 1 d . . N5 N 0.41516(11) 0.4514(6) 0.5704(3) 0.0421(7) Uani 1 1 d D . H5 H 0.4216(17) 0.292(4) 0.553(5) 0.065(16) Uiso 1 1 d D . C1 C 0.23593(13) 0.5730(8) 0.1368(4) 0.0459(9) Uani 1 1 d . . C2 C 0.17189(16) 0.3656(12) 0.0404(4) 0.0687(14) Uani 1 1 d . . H2 H 0.148560 0.280398 0.001690 0.082 Uiso 1 1 calc R U C3 C 0.28876(13) 0.5958(7) 0.2949(4) 0.0469(9) Uani 1 1 d . . C4 C 0.31413(14) 0.3832(8) 0.2979(4) 0.0497(9) Uani 1 1 d . . H4 H 0.319026 0.292976 0.225375 0.060 Uiso 1 1 calc R U C5 C 0.33242(14) 0.3037(7) 0.4100(4) 0.0467(9) Uani 1 1 d . . H5A H 0.349944 0.156481 0.414130 0.056 Uiso 1 1 calc R U C6 C 0.32546(12) 0.4369(7) 0.5171(4) 0.0423(9) Uani 1 1 d . . C7 C 0.30010(13) 0.6518(8) 0.5088(4) 0.0462(9) Uani 1 1 d . . H7 H 0.295316 0.745518 0.580478 0.055 Uiso 1 1 calc R U C8 C 0.28162(13) 0.7326(8) 0.3980(4) 0.0490(9) Uani 1 1 d . . H8 H 0.264232 0.880413 0.393168 0.059 Uiso 1 1 calc R U C9 C 0.34631(12) 0.3501(8) 0.6365(3) 0.0450(9) Uani 1 1 d . . H91 H 0.351111 0.160853 0.633891 0.054 Uiso 1 1 calc R U H92 H 0.328126 0.385238 0.702247 0.054 Uiso 1 1 calc R U C10 C 0.38768(13) 0.4903(7) 0.6655(3) 0.0417(9) Uani 1 1 d . . H10 H 0.381869 0.680114 0.670072 0.050 Uiso 1 1 calc R U C11 C 0.40683(13) 0.4052(9) 0.7896(4) 0.0507(10) Uani 1 1 d . . C12 C 0.4448(2) 0.0929(15) 0.9039(5) 0.093(2) Uani 1 1 d . . H121 H 0.456661 -0.079166 0.893460 0.139 Uiso 1 1 calc R U H122 H 0.423667 0.082243 0.962115 0.139 Uiso 1 1 calc R U H123 H 0.466371 0.213170 0.934848 0.139 Uiso 1 1 calc R U C13 C 0.42098(12) 0.6441(7) 0.4909(4) 0.0415(8) Uani 1 1 d . . C14 C 0.44743(17) 0.7220(8) 0.2930(4) 0.0584(12) Uani 1 1 d . . C15 C 0.40908(18) 0.8649(14) 0.2420(5) 0.0750(15) Uani 1 1 d . . H151 H 0.386449 0.741325 0.227061 0.113 Uiso 1 1 calc R U H152 H 0.414499 0.949725 0.165320 0.113 Uiso 1 1 calc R U H153 H 0.401586 0.995785 0.300679 0.113 Uiso 1 1 calc R U C16 C 0.4630(3) 0.5393(11) 0.2014(6) 0.116(3) Uani 1 1 d . . H161 H 0.485400 0.434708 0.240469 0.174 Uiso 1 1 calc R U H162 H 0.473122 0.638587 0.134217 0.174 Uiso 1 1 calc R U H163 H 0.440626 0.425195 0.169764 0.174 Uiso 1 1 calc R U C17 C 0.48143(16) 0.9098(12) 0.3384(5) 0.0683(13) Uani 1 1 d . . H171 H 0.471230 1.025466 0.399703 0.102 Uiso 1 1 calc R U H172 H 0.489824 1.012686 0.269878 0.102 Uiso 1 1 calc R U H173 H 0.505052 0.811888 0.374719 0.102 Uiso 1 1 calc R U 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 0.0707(19) 0.0514(17) 0.0482(17) 0.0116(13) 0.0001(14) -0.0108(15) O2 0.143(4) 0.148(5) 0.051(2) -0.034(3) -0.016(2) 0.075(4) O3 0.145(4) 0.071(2) 0.0404(18) 0.0054(16) 0.000(2) 0.031(3) O4 0.0663(16) 0.0314(12) 0.0433(14) -0.0006(11) 0.0084(11) 0.0015(13) O5 0.097(2) 0.0322(13) 0.0441(16) 0.0006(12) 0.0283(15) 0.0015(15) N1 0.064(2) 0.067(2) 0.0429(19) 0.0109(17) 0.0033(15) -0.012(2) N2 0.077(3) 0.098(4) 0.048(2) 0.024(2) -0.0043(19) -0.029(3) N3 0.067(2) 0.072(3) 0.045(2) 0.0146(19) 0.0034(17) 0.007(2) N4 0.070(2) 0.053(2) 0.0437(19) 0.0119(16) 0.0035(17) 0.0068(18) N5 0.0584(19) 0.0312(15) 0.0379(17) -0.0010(12) 0.0114(13) 0.0017(13) C1 0.062(2) 0.044(2) 0.0334(18) 0.0075(16) 0.0097(16) 0.0029(18) C2 0.069(3) 0.090(4) 0.045(2) 0.018(3) -0.005(2) -0.017(3) C3 0.059(2) 0.039(2) 0.042(2) 0.0049(16) 0.0034(17) -0.0050(18) C4 0.068(2) 0.043(2) 0.039(2) -0.0079(17) 0.0087(17) 0.001(2) C5 0.059(2) 0.0373(19) 0.045(2) -0.0058(16) 0.0088(17) 0.0005(16) C6 0.051(2) 0.0347(18) 0.042(2) -0.0060(15) 0.0110(15) -0.0070(16) C7 0.055(2) 0.0411(19) 0.043(2) -0.0103(16) 0.0098(17) -0.0028(18) C8 0.056(2) 0.0378(19) 0.054(2) -0.0076(18) 0.0103(18) -0.0009(18) C9 0.059(2) 0.0390(19) 0.0379(19) -0.0014(16) 0.0105(16) -0.0039(18) C10 0.057(2) 0.0352(17) 0.0336(19) -0.0013(15) 0.0084(16) 0.0028(16) C11 0.059(2) 0.055(2) 0.039(2) -0.0055(19) 0.0095(16) 0.002(2) C12 0.123(5) 0.110(5) 0.045(3) 0.020(3) 0.005(3) 0.037(5) C13 0.052(2) 0.0329(16) 0.040(2) -0.0011(14) 0.0065(15) -0.0017(15) C14 0.097(4) 0.037(2) 0.045(2) 0.0035(18) 0.024(2) 0.000(2) C15 0.083(3) 0.090(4) 0.050(3) 0.021(3) -0.001(2) -0.011(3) C16 0.239(10) 0.049(3) 0.074(4) -0.003(3) 0.091(5) -0.003(4) C17 0.070(3) 0.066(3) 0.071(3) 0.020(3) 0.018(2) -0.004(3) 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 C1 O1 C3 117.7(3) C11 O3 C12 116.1(4) C13 O5 C14 120.7(3) C1 N1 N2 116.0(4) C2 N2 N1 117.0(4) C2 N3 N4 116.9(4) N3 N4 C1 116.4(4) C13 N5 C10 119.8(3) C13 N5 H5 120(4) C10 N5 H5 117(4) N1 C1 O1 119.0(4) N1 C1 N4 126.8(4) O1 C1 N4 114.2(4) N3 C2 N2 126.7(5) N3 C2 H2 116.6 N2 C2 H2 116.6 C4 C3 C8 122.2(4) C4 C3 O1 119.2(4) C8 C3 O1 118.6(4) C3 C4 C5 118.2(4) C3 C4 H4 120.9 C5 C4 H4 120.9 C4 C5 C6 121.1(4) C4 C5 H5A 119.5 C6 C5 H5A 119.5 C7 C6 C5 118.4(4) C7 C6 C9 121.6(3) C5 C6 C9 119.9(4) C8 C7 C6 121.1(4) C8 C7 H7 119.4 C6 C7 H7 119.4 C3 C8 C7 119.0(4) C3 C8 H8 120.5 C7 C8 H8 120.5 C6 C9 C10 111.6(3) C6 C9 H91 109.3 C10 C9 H91 109.3 C6 C9 H92 109.3 C10 C9 H92 109.3 H91 C9 H92 108.0 N5 C10 C11 112.1(3) N5 C10 C9 111.7(3) C11 C10 C9 109.8(3) N5 C10 H10 107.7 C11 C10 H10 107.7 C9 C10 H10 107.7 O2 C11 O3 121.9(5) O2 C11 C10 124.4(4) O3 C11 C10 113.7(4) O3 C12 H121 109.5 O3 C12 H122 109.5 H121 C12 H122 109.5 O3 C12 H123 109.5 H121 C12 H123 109.5 H122 C12 H123 109.5 O4 C13 O5 125.3(4) O4 C13 N5 124.6(4) O5 C13 N5 110.1(3) O5 C14 C16 103.3(4) O5 C14 C15 111.0(4) C16 C14 C15 111.8(6) O5 C14 C17 108.8(4) C16 C14 C17 110.0(5) C15 C14 C17 111.6(4) C14 C15 H151 109.5 C14 C15 H152 109.5 H151 C15 H152 109.5 C14 C15 H153 109.5 H151 C15 H153 109.5 H152 C15 H153 109.5 C14 C16 H161 109.5 C14 C16 H162 109.5 H161 C16 H162 109.5 C14 C16 H163 109.5 H161 C16 H163 109.5 H162 C16 H163 109.5 C14 C17 H171 109.5 C14 C17 H172 109.5 H171 C17 H172 109.5 C14 C17 H173 109.5 H171 C17 H173 109.5 H172 C17 H173 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C1 1.333(6) O1 C3 1.415(5) O2 C11 1.187(6) O3 C11 1.303(6) O3 C12 1.450(6) O4 C13 1.217(5) O5 C13 1.341(5) O5 C14 1.470(5) N1 C1 1.322(5) N1 N2 1.328(6) N2 C2 1.323(6) N3 C2 1.317(7) N3 N4 1.318(6) N4 C1 1.334(5) N5 C13 1.349(5) N5 C10 1.449(5) N5 H5 0.873(14) C2 H2 0.9500 C3 C4 1.374(6) C3 C8 1.374(6) C4 C5 1.389(6) C4 H4 0.9500 C5 C6 1.399(5) C5 H5A 0.9500 C6 C7 1.383(6) C6 C9 1.500(6) C7 C8 1.381(6) C7 H7 0.9500 C8 H8 0.9500 C9 C10 1.543(6) C9 H91 0.9900 C9 H92 0.9900 C10 C11 1.521(6) C10 H10 1.0000 C12 H121 0.9800 C12 H122 0.9800 C12 H123 0.9800 C14 C16 1.499(7) C14 C15 1.521(8) C14 C17 1.527(8) C15 H151 0.9800 C15 H152 0.9800 C15 H153 0.9800 C16 H161 0.9800 C16 H162 0.9800 C16 H163 0.9800 C17 H171 0.9800 C17 H172 0.9800 C17 H173 0.9800 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 N5 H5 O4 0.873(14) 2.25(2) 3.078(4) 159(5) 1_545 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 C1 N1 N2 C2 -1.2(8) C2 N3 N4 C1 0.5(7) N2 N1 C1 O1 -176.9(4) N2 N1 C1 N4 5.2(7) C3 O1 C1 N1 -2.0(6) C3 O1 C1 N4 176.0(4) N3 N4 C1 N1 -4.9(7) N3 N4 C1 O1 177.2(4) N4 N3 C2 N2 3.2(9) N1 N2 C2 N3 -2.9(9) C1 O1 C3 C4 85.0(5) C1 O1 C3 C8 -97.9(5) C8 C3 C4 C5 1.1(6) O1 C3 C4 C5 178.1(4) C3 C4 C5 C6 -0.4(6) C4 C5 C6 C7 -0.5(6) C4 C5 C6 C9 -178.7(4) C5 C6 C7 C8 0.7(6) C9 C6 C7 C8 178.9(4) C4 C3 C8 C7 -0.9(6) O1 C3 C8 C7 -178.0(4) C6 C7 C8 C3 0.0(6) C7 C6 C9 C10 -86.7(4) C5 C6 C9 C10 91.5(4) C13 N5 C10 C11 -132.2(4) C13 N5 C10 C9 104.0(4) C6 C9 C10 N5 -57.4(4) C6 C9 C10 C11 177.6(3) C12 O3 C11 O2 0.6(9) C12 O3 C11 C10 -179.2(5) N5 C10 C11 O2 136.9(6) C9 C10 C11 O2 -98.3(6) N5 C10 C11 O3 -43.3(5) C9 C10 C11 O3 81.5(5) C14 O5 C13 O4 -2.2(7) C14 O5 C13 N5 179.4(4) C10 N5 C13 O4 17.6(6) C10 N5 C13 O5 -163.9(3) C13 O5 C14 C16 -175.7(5) C13 O5 C14 C15 -55.8(6) C13 O5 C14 C17 67.4(6)