#------------------------------------------------------------------------------ #$Date: 2020-06-03 05:53:35 +0300 (Wed, 03 Jun 2020) $ #$Revision: 252561 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240592.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_7240592 loop_ _publ_author_name 'Poirier, Marion' 'Pujol-Gim\'enez, Jonai' 'Manatschal, Cristina' 'B\"uhlmann, Sven' 'Embaby, Ahmed' 'Javor, Sacha' 'Hediger, Matthias A.' 'Reymond, Jean-Louis' _publ_section_title ; Pyrazolyl-pyrimidones inhibit the function of human solute carrier protein SLC11A2 (hDMT1) by metal chelation ; _journal_name_full 'RSC Medicinal Chemistry' _journal_paper_doi 10.1039/D0MD00085J _journal_year 2020 _chemical_formula_moiety 'C13 H16 N4 O' _chemical_formula_sum 'C13 H16 N4 O' _chemical_formula_weight 244.3 _chemical_name_systematic 6-methyl-2-(3-methyl-4,5,6,7-tetrahydro-2H-indazol-2-yl)pyrimidin-4(3H)-one _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_cell_setting triclinic _symmetry_Int_Tables_number 2 _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens mixed _audit_creation_date 2016-09-06T14:31:06-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_update_record ; 2020-01-10 deposited with the CCDC. 2020-05-07 downloaded from the CCDC. ; _cell_angle_alpha 93.396(3) _cell_angle_beta 99.154(3) _cell_angle_gamma 117.195(4) _cell_formula_units_Z 4 _cell_length_a 8.1640(3) _cell_length_b 8.5511(4) _cell_length_c 19.8770(7) _cell_measurement_reflns_used 4470 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 27.441 _cell_measurement_theta_min 2.085 _cell_volume 1204.69(10) _computing_cell_refinement 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 173(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.0965 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 0.912 _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Single source at offset, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.013067 _diffrn_orient_matrix_UB_12 -0.0014783 _diffrn_orient_matrix_UB_13 0.0360541 _diffrn_orient_matrix_UB_21 0.0711968 _diffrn_orient_matrix_UB_22 -0.0250241 _diffrn_orient_matrix_UB_23 -0.0015312 _diffrn_orient_matrix_UB_31 0.0688495 _diffrn_orient_matrix_UB_32 0.0909367 _diffrn_orient_matrix_UB_33 0.0058633 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0309 _diffrn_reflns_av_unetI/netI 0.0464 _diffrn_reflns_Laue_measured_fraction_full 1 _diffrn_reflns_Laue_measured_fraction_max 0.912 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_number 16639 _diffrn_reflns_point_group_measured_fraction_full 1 _diffrn_reflns_point_group_measured_fraction_max 0.912 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.259 _diffrn_reflns_theta_min 2.099 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.09 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_correction_T_min 0.76978 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.347 _exptl_crystal_description plate _exptl_crystal_F_000 520 _exptl_crystal_size_max 0.373 _exptl_crystal_size_mid 0.172 _exptl_crystal_size_min 0.03 _refine_diff_density_max 0.392 _refine_diff_density_min -0.218 _refine_diff_density_rms 0.041 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 354 _refine_ls_number_reflns 5444 _refine_ls_number_restraints 30 _refine_ls_restrained_S_all 1.011 _refine_ls_R_factor_all 0.0726 _refine_ls_R_factor_gt 0.0484 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0482P)^2^+0.4126P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1063 _refine_ls_wR_factor_ref 0.1186 _reflns_Friedel_coverage 0 _reflns_number_gt 3996 _reflns_number_total 5444 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0md00085j3.cif _cod_data_source_block 16jlr002 _cod_original_cell_volume 1204.68(9) _cod_database_code 7240592 _shelx_res_file ; shelx.res created by SHELXL-2014/7 TITL 16JLR002 in P-1 CELL 0.71073 8.163967 8.551063 19.877029 93.3965 99.1541 117.1947 ZERR 4.00 0.000314 0.000373 0.000739 0.0033 0.0032 0.0041 LATT 1 SFAC C H N O UNIT 52 64 16 4 MERG 2 RIGU C9 C10A C10B C11A C11B C12 FMAP 2 PLAN 20 ACTA BOND $H CONF L.S. 10 TEMP -100.00 WGHT 0.048200 0.412600 FVAR 3.22621 0.85533 C1 1 0.675695 0.482922 0.927506 11.00000 0.02294 0.02341 = 0.02272 0.00377 0.00297 0.01195 C2 1 0.572326 0.494835 0.807827 11.00000 0.03423 0.03213 = 0.02511 0.00553 0.00166 0.01447 C3 1 0.410648 0.330464 0.810405 11.00000 0.02603 0.03021 = 0.02601 0.00215 -0.00066 0.01218 AFIX 43 H3 2 0.311657 0.273599 0.770793 11.00000 -1.20000 AFIX 0 C4 1 0.397689 0.255403 0.868842 11.00000 0.02152 0.02499 = 0.02652 0.00099 0.00239 0.01226 C5 1 0.238641 0.077440 0.872187 11.00000 0.02508 0.02923 = 0.03222 0.00199 0.00081 0.00848 AFIX 137 H5A 2 0.145263 0.035414 0.828706 11.00000 -1.50000 H5B 2 0.179511 0.087740 0.910250 11.00000 -1.50000 H5C 2 0.286996 -0.007375 0.879793 11.00000 -1.50000 AFIX 0 C6 1 0.830381 0.534656 1.052663 11.00000 0.02199 0.02276 = 0.02383 0.00467 0.00395 0.01093 C7 1 0.692980 0.371515 1.075336 11.00000 0.02939 0.02651 = 0.02562 0.00823 0.00493 0.00859 AFIX 137 H7A 2 0.566657 0.360524 1.063121 11.00000 -1.50000 H7B 2 0.728320 0.379473 1.125389 11.00000 -1.50000 H7C 2 0.693438 0.267062 1.052436 11.00000 -1.50000 AFIX 0 C8 1 0.991747 0.674509 1.090590 11.00000 0.02259 0.02313 = 0.02544 0.00335 0.00322 0.01192 C9 1 1.073926 0.710792 1.166356 11.00000 0.02822 0.03152 = 0.02470 0.00544 0.00231 0.01343 PART 1 AFIX 23 H9A1 2 1.083250 0.605689 1.180645 21.00000 -1.20000 H9A2 2 0.989200 0.730870 1.192082 21.00000 -1.20000 AFIX 23 PART 2 H9B1 2 1.141738 0.641881 1.177893 -21.00000 -1.20000 H9B2 2 0.974088 0.679438 1.193332 -21.00000 -1.20000 AFIX 0 PART 0 PART 1 C10A 1 1.267954 0.872445 1.184356 21.00000 0.02669 0.03115 = 0.02576 0.00408 -0.00050 0.01411 AFIX 23 H10A 2 1.362465 0.836862 1.174654 21.00000 -1.20000 H10B 2 1.299081 0.916701 1.234286 21.00000 -1.20000 AFIX 0 C11A 1 1.280069 1.022903 1.143706 21.00000 0.02333 0.02285 = 0.03390 0.00138 0.00265 0.00603 AFIX 23 H11A 2 1.406308 1.127262 1.159453 21.00000 -1.20000 H11B 2 1.185610 1.058547 1.153419 21.00000 -1.20000 AFIX 0 PART 2 C10B 1 1.221654 0.928054 1.182441 -21.00000 0.03116 0.02950 = 0.03708 0.00676 -0.00395 0.01022 AFIX 23 H10C 2 1.147162 0.992696 1.181202 -21.00000 -1.20000 H10D 2 1.298460 0.956799 1.229692 -21.00000 -1.20000 AFIX 0 C11B 1 1.349862 0.993798 1.133946 -21.00000 0.03380 0.03560 = 0.04003 0.00263 0.00284 0.00858 AFIX 23 H11C 2 1.438376 1.121887 1.148954 -21.00000 -1.20000 H11D 2 1.424526 0.929443 1.134318 -21.00000 -1.20000 AFIX 0 PART 0 C12 1 1.245510 0.968223 1.065411 11.00000 0.02353 0.02466 = 0.03444 0.00532 0.00213 0.00456 PART 1 AFIX 23 H12A 2 1.232431 1.060125 1.040502 21.00000 -1.20000 H12B 2 1.353284 0.956289 1.053914 21.00000 -1.20000 AFIX 23 PART 2 H12C 2 1.328092 0.978072 1.032646 -21.00000 -1.20000 H12D 2 1.212152 1.065486 1.061433 -21.00000 -1.20000 AFIX 0 PART 0 C13 1 1.068905 0.794322 1.044346 11.00000 0.02249 0.02339 = 0.02619 0.00348 0.00342 0.01124 C14 1 -0.231997 -0.013940 0.527841 11.00000 0.02361 0.02422 = 0.02108 0.00341 0.00281 0.01279 C15 1 -0.109102 0.013687 0.649215 11.00000 0.03220 0.03198 = 0.02261 0.00452 0.00284 0.01877 C16 1 -0.277234 -0.150365 0.646237 11.00000 0.03438 0.02996 = 0.02385 0.00905 0.00653 0.01724 AFIX 43 H16 2 -0.300048 -0.202255 0.686981 11.00000 -1.20000 AFIX 0 C17 1 -0.404192 -0.232385 0.585863 11.00000 0.02782 0.02569 = 0.02694 0.00625 0.00704 0.01549 C18 1 -0.576684 -0.406970 0.580574 11.00000 0.03156 0.02761 = 0.02947 0.00785 0.00824 0.01093 AFIX 137 H18A 2 -0.582988 -0.443514 0.626305 11.00000 -1.50000 H18B 2 -0.571403 -0.496828 0.549322 11.00000 -1.50000 H18C 2 -0.688719 -0.394999 0.562629 11.00000 -1.50000 AFIX 0 C19 1 -0.301474 0.015991 0.402395 11.00000 0.02303 0.02421 = 0.02274 0.00405 0.00183 0.01090 C20 1 -0.477110 -0.154749 0.376713 11.00000 0.02956 0.02634 = 0.02699 0.00567 -0.00114 0.00305 AFIX 137 H20A 2 -0.451746 -0.254320 0.384793 11.00000 -1.50000 H20B 2 -0.520937 -0.162005 0.327213 11.00000 -1.50000 H20C 2 -0.574338 -0.160387 0.401215 11.00000 -1.50000 AFIX 0 C21 1 -0.207492 0.150481 0.367249 11.00000 0.02327 0.02363 = 0.02463 0.00496 0.00402 0.01052 C22 1 -0.048429 0.281110 0.415555 11.00000 0.02364 0.02500 = 0.02434 0.00517 0.00387 0.01182 C23 1 0.092757 0.453360 0.398332 11.00000 0.02580 0.02326 = 0.03035 0.00604 0.00378 0.00508 AFIX 23 H23A 2 0.212367 0.450280 0.397955 11.00000 -1.20000 H23B 2 0.118556 0.552611 0.433798 11.00000 -1.20000 AFIX 0 C24 1 0.016347 0.483450 0.327460 11.00000 0.03983 0.02836 = 0.03962 0.01362 0.00189 0.00292 AFIX 23 H24A 2 -0.076789 0.525198 0.332032 11.00000 -1.20000 H24B 2 0.121141 0.577902 0.310999 11.00000 -1.20000 AFIX 0 C25 1 -0.075782 0.317023 0.274692 11.00000 0.04124 0.04137 = 0.03022 0.01293 0.00309 0.00637 AFIX 23 H25A 2 0.015606 0.272353 0.271366 11.00000 -1.20000 H25B 2 -0.111079 0.346370 0.229017 11.00000 -1.20000 AFIX 0 C26 1 -0.251313 0.171284 0.293328 11.00000 0.02926 0.02867 = 0.02564 0.00615 -0.00034 0.00774 AFIX 23 H26A 2 -0.354566 0.203001 0.285848 11.00000 -1.20000 H26B 2 -0.293168 0.057550 0.263370 11.00000 -1.20000 AFIX 0 N1 3 0.702919 0.563753 0.870759 11.00000 0.02738 0.02403 = 0.02485 0.00660 0.00274 0.00600 N2 3 0.531345 0.332715 0.929829 11.00000 0.02115 0.02364 = 0.02504 0.00382 0.00116 0.00896 N3 3 0.816853 0.574687 0.986186 11.00000 0.02253 0.01927 = 0.02428 0.00503 0.00312 0.00610 N4 3 0.964963 0.736774 0.981026 11.00000 0.02305 0.02077 = 0.02985 0.00609 0.00360 0.00545 N5 3 -0.097772 0.074778 0.585693 11.00000 0.02450 0.02445 = 0.02292 0.00245 0.00114 0.00728 N6 3 -0.383525 -0.163462 0.524597 11.00000 0.02710 0.02493 = 0.02356 0.00682 0.00442 0.01066 N7 3 -0.197264 0.068514 0.469532 11.00000 0.02283 0.02111 = 0.02320 0.00365 0.00226 0.00582 N8 3 -0.039965 0.233347 0.477528 11.00000 0.02280 0.02221 = 0.02664 0.00414 0.00290 0.00545 O1 4 0.605182 0.574902 0.758517 11.00000 0.05377 0.04520 = 0.02903 0.01534 0.00183 0.00898 O2 4 0.017833 0.099053 0.699670 11.00000 0.03784 0.04142 = 0.02380 0.00046 -0.00516 0.01448 H1 2 0.806798 0.665222 0.874197 11.00000 -1.20000 H5 2 0.001553 0.176582 0.582280 11.00000 -1.20000 HKLF 4 REM 16JLR002 in P-1 REM R1 = 0.0484 for 3996 Fo > 4sig(Fo) and 0.0726 for all 5444 data REM 354 parameters refined using 30 restraints END WGHT 0.0478 0.3965 REM Highest difference peak 0.392, deepest hole -0.218, 1-sigma level 0.041 Q1 1 -0.1407 0.4016 0.2922 11.00000 0.05 0.39 Q2 1 -0.1206 0.2267 0.3851 11.00000 0.05 0.24 Q3 1 1.0231 0.6836 1.1230 11.00000 0.05 0.23 Q4 1 0.0419 0.3316 0.4001 11.00000 0.05 0.21 Q5 1 0.3044 0.1703 0.8735 11.00000 0.05 0.21 Q6 1 -0.1826 -0.0998 0.6398 11.00000 0.05 0.21 Q7 1 1.0182 0.7666 1.0788 11.00000 0.05 0.20 Q8 1 -0.5433 -0.2438 0.4017 11.00000 0.05 0.20 Q9 1 1.1653 0.8013 1.1739 11.00000 0.05 0.20 Q10 1 -0.3328 -0.0611 0.5315 11.00000 0.05 0.20 Q11 1 0.4730 0.4243 0.8130 11.00000 0.05 0.20 Q12 1 1.0671 0.7079 1.0667 11.00000 0.05 0.20 Q13 1 1.1722 0.8679 1.0499 11.00000 0.05 0.19 Q14 1 0.8791 0.6437 1.0832 11.00000 0.05 0.19 Q15 1 0.0057 0.2422 0.4408 11.00000 0.05 0.19 Q16 1 -0.3163 0.0849 0.3824 11.00000 0.05 0.18 Q17 1 -0.2486 0.0521 0.3750 11.00000 0.05 0.18 Q18 1 0.5184 0.3871 0.8010 11.00000 0.05 0.18 Q19 1 0.9344 0.5639 1.0647 11.00000 0.05 0.18 Q20 1 -0.2306 -0.0354 0.6534 11.00000 0.05 0.18 ; _shelx_res_checksum 40340 loop_ _symmetry_equiv_pos_as_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 C1 C 0.6757(2) 0.4829(2) 0.92751(8) 0.0228(3) Uani 1 1 d . . . . . C2 C 0.5723(2) 0.4948(2) 0.80783(8) 0.0315(4) Uani 1 1 d . . . . . C3 C 0.4106(2) 0.3305(2) 0.81040(8) 0.0287(4) Uani 1 1 d . . . . . H3 H 0.3117 0.2736 0.7708 0.034 Uiso 1 1 calc R U . . . C4 C 0.3977(2) 0.2554(2) 0.86884(8) 0.0243(3) Uani 1 1 d . . . . . C5 C 0.2386(2) 0.0774(2) 0.87219(9) 0.0314(4) Uani 1 1 d . . . . . H5A H 0.1453 0.0354 0.8287 0.047 Uiso 1 1 calc R U . . . H5B H 0.1795 0.0877 0.9103 0.047 Uiso 1 1 calc R U . . . H5C H 0.287 -0.0074 0.8798 0.047 Uiso 1 1 calc R U . . . C6 C 0.8304(2) 0.5347(2) 1.05266(8) 0.0228(3) Uani 1 1 d . . . . . C7 C 0.6930(2) 0.3715(2) 1.07534(8) 0.0289(4) Uani 1 1 d . . . . . H7A H 0.5667 0.3605 1.0631 0.043 Uiso 1 1 calc R U . . . H7B H 0.7283 0.3795 1.1254 0.043 Uiso 1 1 calc R U . . . H7C H 0.6934 0.2671 1.0524 0.043 Uiso 1 1 calc R U . . . C8 C 0.9917(2) 0.6745(2) 1.09059(8) 0.0235(3) Uani 1 1 d . . . . . C9 C 1.0739(2) 0.7108(2) 1.16636(8) 0.0288(4) Uani 1 1 d . U . . . H9A1 H 1.0832 0.6057 1.1806 0.035 Uiso 0.855(9) 1 calc R U P A 1 H9A2 H 0.9892 0.7309 1.1921 0.035 Uiso 0.855(9) 1 calc R U P A 1 H9B1 H 1.1417 0.6419 1.1779 0.035 Uiso 0.145(9) 1 calc R U P A 2 H9B2 H 0.9741 0.6794 1.1933 0.035 Uiso 0.145(9) 1 calc R U P A 2 C10A C 1.2680(3) 0.8724(4) 1.18436(11) 0.0285(6) Uani 0.855(9) 1 d . U P A 1 H10A H 1.3625 0.8369 1.1747 0.034 Uiso 0.855(9) 1 calc R U P A 1 H10B H 1.2991 0.9167 1.2343 0.034 Uiso 0.855(9) 1 calc R U P A 1 C11A C 1.2801(4) 1.0229(3) 1.14371(12) 0.0292(7) Uani 0.855(9) 1 d . U P A 1 H11A H 1.4063 1.1273 1.1595 0.035 Uiso 0.855(9) 1 calc R U P A 1 H11B H 1.1856 1.0585 1.1534 0.035 Uiso 0.855(9) 1 calc R U P A 1 C10B C 1.222(3) 0.928(2) 1.1824(8) 0.036(4) Uani 0.145(9) 1 d . U P A 2 H10C H 1.1472 0.9927 1.1812 0.043 Uiso 0.145(9) 1 calc R U P A 2 H10D H 1.2985 0.9568 1.2297 0.043 Uiso 0.145(9) 1 calc R U P A 2 C11B C 1.350(3) 0.994(2) 1.1339(8) 0.040(4) Uani 0.145(9) 1 d . U P A 2 H11C H 1.4384 1.1219 1.149 0.048 Uiso 0.145(9) 1 calc R U P A 2 H11D H 1.4245 0.9294 1.1343 0.048 Uiso 0.145(9) 1 calc R U P A 2 C12 C 1.2455(2) 0.9682(2) 1.06541(9) 0.0307(4) Uani 1 1 d . U . . . H12A H 1.2324 1.0601 1.0405 0.037 Uiso 0.855(9) 1 calc R U P A 1 H12B H 1.3533 0.9563 1.0539 0.037 Uiso 0.855(9) 1 calc R U P A 1 H12C H 1.3281 0.9781 1.0326 0.037 Uiso 0.145(9) 1 calc R U P A 2 H12D H 1.2122 1.0655 1.0614 0.037 Uiso 0.145(9) 1 calc R U P A 2 C13 C 1.0689(2) 0.7943(2) 1.04435(8) 0.0241(3) Uani 1 1 d . . . . . C14 C -0.2320(2) -0.0139(2) 0.52784(8) 0.0226(3) Uani 1 1 d . . . . . C15 C -0.1091(2) 0.0137(2) 0.64922(8) 0.0278(4) Uani 1 1 d . . . . . C16 C -0.2772(2) -0.1504(2) 0.64624(8) 0.0283(4) Uani 1 1 d . . . . . H16 H -0.3 -0.2023 0.687 0.034 Uiso 1 1 calc R U . . . C17 C -0.4042(2) -0.2324(2) 0.58586(8) 0.0254(3) Uani 1 1 d . . . . . C18 C -0.5767(2) -0.4070(2) 0.58057(9) 0.0304(4) Uani 1 1 d . . . . . H18A H -0.583 -0.4435 0.6263 0.046 Uiso 1 1 calc R U . . . H18B H -0.5714 -0.4968 0.5493 0.046 Uiso 1 1 calc R U . . . H18C H -0.6887 -0.395 0.5626 0.046 Uiso 1 1 calc R U . . . C19 C -0.3015(2) 0.0160(2) 0.40239(8) 0.0238(3) Uani 1 1 d . . . . . C20 C -0.4771(2) -0.1547(2) 0.37671(9) 0.0325(4) Uani 1 1 d . . . . . H20A H -0.4517 -0.2543 0.3848 0.049 Uiso 1 1 calc R U . . . H20B H -0.5209 -0.162 0.3272 0.049 Uiso 1 1 calc R U . . . H20C H -0.5743 -0.1604 0.4012 0.049 Uiso 1 1 calc R U . . . C21 C -0.2075(2) 0.1505(2) 0.36725(8) 0.0241(3) Uani 1 1 d . . . . . C22 C -0.0484(2) 0.2811(2) 0.41555(8) 0.0243(3) Uani 1 1 d . . . . . C23 C 0.0928(2) 0.4534(2) 0.39833(8) 0.0292(4) Uani 1 1 d . . . . . H23A H 0.2124 0.4503 0.398 0.035 Uiso 1 1 calc R U . . . H23B H 0.1186 0.5526 0.4338 0.035 Uiso 1 1 calc R U . . . C24 C 0.0163(3) 0.4835(2) 0.32746(9) 0.0416(5) Uani 1 1 d . . . . . H24A H -0.0768 0.5252 0.332 0.05 Uiso 1 1 calc R U . . . H24B H 0.1211 0.5779 0.311 0.05 Uiso 1 1 calc R U . . . C25 C -0.0758(3) 0.3170(2) 0.27469(9) 0.0431(5) Uani 1 1 d . . . . . H25A H 0.0156 0.2724 0.2714 0.052 Uiso 1 1 calc R U . . . H25B H -0.1111 0.3464 0.229 0.052 Uiso 1 1 calc R U . . . C26 C -0.2513(2) 0.1713(2) 0.29333(8) 0.0309(4) Uani 1 1 d . . . . . H26A H -0.3546 0.203 0.2858 0.037 Uiso 1 1 calc R U . . . H26B H -0.2932 0.0575 0.2634 0.037 Uiso 1 1 calc R U . . . N1 N 0.7029(2) 0.56375(18) 0.87076(7) 0.0281(3) Uani 1 1 d . . . . . N2 N 0.53135(18) 0.33271(17) 0.92983(7) 0.0244(3) Uani 1 1 d . . . . . N3 N 0.81685(18) 0.57469(16) 0.98619(6) 0.0237(3) Uani 1 1 d . . . . . N4 N 0.96496(18) 0.73677(16) 0.98103(7) 0.0267(3) Uani 1 1 d . . . . . N5 N -0.0978(2) 0.07478(18) 0.58569(7) 0.0262(3) Uani 1 1 d . . . . . N6 N -0.38353(19) -0.16346(17) 0.52460(6) 0.0258(3) Uani 1 1 d . . . . . N7 N -0.19726(18) 0.06851(16) 0.46953(6) 0.0245(3) Uani 1 1 d . . . . . N8 N -0.03997(18) 0.23335(17) 0.47753(7) 0.0262(3) Uani 1 1 d . . . . . O1 O 0.6052(2) 0.57490(17) 0.75852(6) 0.0488(4) Uani 1 1 d . . . . . O2 O 0.01783(17) 0.09905(16) 0.69967(6) 0.0377(3) Uani 1 1 d . . . . . H1 H 0.807(3) 0.665(3) 0.8742(10) 0.045 Uiso 1 1 d . U . . . H5 H 0.002(3) 0.177(3) 0.5823(10) 0.045 Uiso 1 1 d . 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 C1 0.0229(8) 0.0234(8) 0.0227(8) 0.0038(6) 0.0030(6) 0.0120(7) C2 0.0342(9) 0.0321(9) 0.0251(9) 0.0055(7) 0.0017(7) 0.0145(8) C3 0.0260(9) 0.0302(9) 0.0260(8) 0.0021(7) -0.0007(7) 0.0122(7) C4 0.0215(8) 0.0250(8) 0.0265(8) 0.0010(6) 0.0024(6) 0.0123(7) C5 0.0251(9) 0.0292(9) 0.0322(9) 0.0020(7) 0.0008(7) 0.0085(7) C6 0.0220(8) 0.0228(8) 0.0238(8) 0.0047(6) 0.0040(6) 0.0109(7) C7 0.0294(9) 0.0265(8) 0.0256(8) 0.0082(7) 0.0049(7) 0.0086(7) C8 0.0226(8) 0.0231(8) 0.0254(8) 0.0033(6) 0.0032(6) 0.0119(7) C9 0.0282(9) 0.0315(9) 0.0247(8) 0.0054(7) 0.0023(7) 0.0134(7) C10A 0.0267(12) 0.0312(13) 0.0258(10) 0.0041(9) -0.0005(8) 0.0141(10) C11A 0.0233(13) 0.0229(10) 0.0339(12) 0.0014(9) 0.0026(9) 0.0060(9) C10B 0.031(7) 0.030(6) 0.037(6) 0.007(5) -0.004(5) 0.010(5) C11B 0.034(7) 0.036(7) 0.040(5) 0.003(5) 0.003(5) 0.009(6) C12 0.0235(8) 0.0247(8) 0.0344(9) 0.0053(7) 0.0021(7) 0.0046(7) C13 0.0225(8) 0.0234(8) 0.0262(8) 0.0035(6) 0.0034(7) 0.0112(7) C14 0.0236(8) 0.0242(8) 0.0211(8) 0.0034(6) 0.0028(6) 0.0128(7) C15 0.0322(9) 0.0320(9) 0.0226(8) 0.0045(7) 0.0028(7) 0.0188(8) C16 0.0344(9) 0.0300(8) 0.0239(8) 0.0090(7) 0.0065(7) 0.0172(8) C17 0.0278(9) 0.0257(8) 0.0269(8) 0.0062(6) 0.0070(7) 0.0155(7) C18 0.0316(9) 0.0276(8) 0.0295(9) 0.0079(7) 0.0082(7) 0.0109(8) C19 0.0230(8) 0.0242(8) 0.0227(8) 0.0041(6) 0.0018(6) 0.0109(7) C20 0.0296(9) 0.0263(8) 0.0270(9) 0.0057(7) -0.0011(7) 0.0030(7) C21 0.0233(8) 0.0236(8) 0.0246(8) 0.0050(6) 0.0040(6) 0.0105(7) C22 0.0236(8) 0.0250(8) 0.0243(8) 0.0052(6) 0.0039(6) 0.0118(7) C23 0.0258(9) 0.0233(8) 0.0303(9) 0.0060(7) 0.0038(7) 0.0051(7) C24 0.0398(11) 0.0284(9) 0.0396(11) 0.0136(8) 0.0019(9) 0.0029(8) C25 0.0412(11) 0.0414(11) 0.0302(10) 0.0129(8) 0.0031(8) 0.0064(9) C26 0.0293(9) 0.0287(9) 0.0256(9) 0.0062(7) -0.0003(7) 0.0077(7) N1 0.0274(8) 0.0240(7) 0.0248(7) 0.0066(6) 0.0027(6) 0.0060(6) N2 0.0211(7) 0.0236(7) 0.0250(7) 0.0038(5) 0.0012(5) 0.0090(6) N3 0.0225(7) 0.0193(6) 0.0243(7) 0.0050(5) 0.0031(5) 0.0061(6) N4 0.0230(7) 0.0208(7) 0.0298(7) 0.0061(6) 0.0036(6) 0.0054(6) N5 0.0245(7) 0.0245(7) 0.0229(7) 0.0025(5) 0.0011(6) 0.0073(6) N6 0.0271(7) 0.0249(7) 0.0236(7) 0.0068(5) 0.0044(6) 0.0107(6) N7 0.0228(7) 0.0211(6) 0.0232(7) 0.0037(5) 0.0023(5) 0.0058(6) N8 0.0228(7) 0.0222(7) 0.0266(7) 0.0041(5) 0.0029(6) 0.0055(6) O1 0.0538(9) 0.0452(8) 0.0290(7) 0.0153(6) 0.0018(6) 0.0090(7) O2 0.0378(7) 0.0414(7) 0.0238(6) 0.0005(5) -0.0052(5) 0.0145(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 '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 0.006 '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 N2 C1 N1 124.74(14) . . ? N2 C1 N3 120.47(14) . . ? N1 C1 N3 114.79(14) . . ? O1 C2 N1 119.58(16) . . ? O1 C2 C3 127.72(16) . . ? N1 C2 C3 112.69(14) . . ? C4 C3 C2 120.62(15) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C3 C4 N2 123.59(15) . . ? C3 C4 C5 122.34(15) . . ? N2 C4 C5 114.05(14) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C8 C6 N3 105.60(13) . . ? C8 C6 C7 129.09(14) . . ? N3 C6 C7 125.31(14) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 C13 106.14(14) . . ? C6 C8 C9 130.07(14) . . ? C13 C8 C9 123.67(14) . . ? C8 C9 C10A 111.49(15) . . ? C8 C9 C10B 104.7(5) . . ? C8 C9 H9A1 109.3 . . ? C10A C9 H9A1 109.3 . . ? C8 C9 H9A2 109.3 . . ? C10A C9 H9A2 109.3 . . ? H9A1 C9 H9A2 108 . . ? C8 C9 H9B1 110.8 . . ? C10B C9 H9B1 110.8 . . ? C8 C9 H9B2 110.8 . . ? C10B C9 H9B2 110.8 . . ? H9B1 C9 H9B2 108.9 . . ? C9 C10A C11A 112.4(2) . . ? C9 C10A H10A 109.1 . . ? C11A C10A H10A 109.1 . . ? C9 C10A H10B 109.1 . . ? C11A C10A H10B 109.1 . . ? H10A C10A H10B 107.8 . . ? C10A C11A C12 112.4(2) . . ? C10A C11A H11A 109.1 . . ? C12 C11A H11A 109.1 . . ? C10A C11A H11B 109.1 . . ? C12 C11A H11B 109.1 . . ? H11A C11A H11B 107.9 . . ? C11B C10B C9 114.7(17) . . ? C11B C10B H10C 108.6 . . ? C9 C10B H10C 108.6 . . ? C11B C10B H10D 108.6 . . ? C9 C10B H10D 108.6 . . ? H10C C10B H10D 107.6 . . ? C12 C11B C10B 110.7(18) . . ? C12 C11B H11C 109.5 . . ? C10B C11B H11C 109.5 . . ? C12 C11B H11D 109.5 . . ? C10B C11B H11D 109.5 . . ? H11C C11B H11D 108.1 . . ? C11B C12 C13 115.0(6) . . ? C13 C12 C11A 108.44(15) . . ? C13 C12 H12A 110 . . ? C11A C12 H12A 110 . . ? C13 C12 H12B 110 . . ? C11A C12 H12B 110 . . ? H12A C12 H12B 108.4 . . ? C11B C12 H12C 108.5 . . ? C13 C12 H12C 108.5 . . ? C11B C12 H12D 108.5 . . ? C13 C12 H12D 108.5 . . ? H12C C12 H12D 107.5 . . ? N4 C13 C8 112.27(14) . . ? N4 C13 C12 124.19(14) . . ? C8 C13 C12 123.52(14) . . ? N6 C14 N5 124.74(14) . . ? N6 C14 N7 120.69(14) . . ? N5 C14 N7 114.57(14) . . ? O2 C15 N5 119.80(15) . . ? O2 C15 C16 127.40(15) . . ? N5 C15 C16 112.80(14) . . ? C17 C16 C15 120.82(15) . . ? C17 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? C16 C17 N6 123.15(15) . . ? C16 C17 C18 122.03(15) . . ? N6 C17 C18 114.81(14) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C21 C19 N7 105.59(13) . . ? C21 C19 C20 129.12(14) . . ? N7 C19 C20 125.29(14) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C21 C22 106.36(14) . . ? C19 C21 C26 130.65(14) . . ? C22 C21 C26 122.99(14) . . ? N8 C22 C21 111.96(14) . . ? N8 C22 C23 124.15(14) . . ? C21 C22 C23 123.89(14) . . ? C22 C23 C24 109.81(13) . . ? C22 C23 H23A 109.7 . . ? C24 C23 H23A 109.7 . . ? C22 C23 H23B 109.7 . . ? C24 C23 H23B 109.7 . . ? H23A C23 H23B 108.2 . . ? C25 C24 C23 112.53(15) . . ? C25 C24 H24A 109.1 . . ? C23 C24 H24A 109.1 . . ? C25 C24 H24B 109.1 . . ? C23 C24 H24B 109.1 . . ? H24A C24 H24B 107.8 . . ? C24 C25 C26 111.90(16) . . ? C24 C25 H25A 109.2 . . ? C26 C25 H25A 109.2 . . ? C24 C25 H25B 109.2 . . ? C26 C25 H25B 109.2 . . ? H25A C25 H25B 107.9 . . ? C21 C26 C25 109.59(14) . . ? C21 C26 H26A 109.8 . . ? C25 C26 H26A 109.8 . . ? C21 C26 H26B 109.8 . . ? C25 C26 H26B 109.8 . . ? H26A C26 H26B 108.2 . . ? C1 N1 C2 122.84(14) . . ? C1 N1 H1 118.0(13) . . ? C2 N1 H1 119.2(13) . . ? C1 N2 C4 115.46(13) . . ? C6 N3 N4 112.06(12) . . ? C6 N3 C1 130.00(13) . . ? N4 N3 C1 117.84(12) . . ? C13 N4 N3 103.92(12) . . ? C14 N5 C15 122.79(14) . . ? C14 N5 H5 117.6(13) . . ? C15 N5 H5 119.6(13) . . ? C14 N6 C17 115.68(13) . . ? N8 N7 C19 111.90(12) . . ? N8 N7 C14 117.74(12) . . ? C19 N7 C14 130.29(13) . . ? C22 N8 N7 104.19(12) . . ? 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 C1 N2 1.2967(19) . ? C1 N1 1.353(2) . ? C1 N3 1.393(2) . ? C2 O1 1.223(2) . ? C2 N1 1.401(2) . ? C2 C3 1.433(2) . ? C3 C4 1.356(2) . ? C3 H3 0.95 . ? C4 N2 1.386(2) . ? C4 C5 1.497(2) . ? C5 H5A 0.98 . ? C5 H5B 0.98 . ? C5 H5C 0.98 . ? C6 C8 1.368(2) . ? C6 N3 1.3846(19) . ? C6 C7 1.487(2) . ? C7 H7A 0.98 . ? C7 H7B 0.98 . ? C7 H7C 0.98 . ? C8 C13 1.413(2) . ? C8 C9 1.499(2) . ? C9 C10A 1.519(3) . ? C9 C10B 1.663(16) . ? C9 H9A1 0.99 . ? C9 H9A2 0.99 . ? C9 H9B1 0.99 . ? C9 H9B2 0.99 . ? C10A C11A 1.533(4) . ? C10A H10A 0.99 . ? C10A H10B 0.99 . ? C11A C12 1.541(3) . ? C11A H11A 0.99 . ? C11A H11B 0.99 . ? C10B C11B 1.48(3) . ? C10B H10C 0.99 . ? C10B H10D 0.99 . ? C11B C12 1.433(15) . ? C11B H11C 0.99 . ? C11B H11D 0.99 . ? C12 C13 1.497(2) . ? C12 H12A 0.99 . ? C12 H12B 0.99 . ? C12 H12C 0.99 . ? C12 H12D 0.99 . ? C13 N4 1.323(2) . ? C14 N6 1.2994(19) . ? C14 N5 1.354(2) . ? C14 N7 1.3927(19) . ? C15 O2 1.2262(19) . ? C15 N5 1.395(2) . ? C15 C16 1.435(2) . ? C16 C17 1.359(2) . ? C16 H16 0.95 . ? C17 N6 1.3851(19) . ? C17 C18 1.495(2) . ? C18 H18A 0.98 . ? C18 H18B 0.98 . ? C18 H18C 0.98 . ? C19 C21 1.363(2) . ? C19 N7 1.3874(19) . ? C19 C20 1.488(2) . ? C20 H20A 0.98 . ? C20 H20B 0.98 . ? C20 H20C 0.98 . ? C21 C22 1.416(2) . ? C21 C26 1.497(2) . ? C22 N8 1.322(2) . ? C22 C23 1.500(2) . ? C23 C24 1.533(2) . ? C23 H23A 0.99 . ? C23 H23B 0.99 . ? C24 C25 1.512(3) . ? C24 H24A 0.99 . ? C24 H24B 0.99 . ? C25 C26 1.528(2) . ? C25 H25A 0.99 . ? C25 H25B 0.99 . ? C26 H26A 0.99 . ? C26 H26B 0.99 . ? N1 H1 0.88(2) . ? N3 N4 1.3850(17) . ? N5 H5 0.89(2) . ? N7 N8 1.3839(17) . ? 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 O1 C2 C3 C4 177.92(18) . . . . ? N1 C2 C3 C4 -1.6(2) . . . . ? C2 C3 C4 N2 2.9(3) . . . . ? C2 C3 C4 C5 -175.26(15) . . . . ? N3 C6 C8 C13 0.09(17) . . . . ? C7 C6 C8 C13 -179.62(16) . . . . ? N3 C6 C8 C9 176.22(15) . . . . ? C7 C6 C8 C9 -3.5(3) . . . . ? C6 C8 C9 C10A 173.3(2) . . . . ? C13 C8 C9 C10A -11.2(3) . . . . ? C6 C8 C9 C10B -160.3(9) . . . . ? C13 C8 C9 C10B 15.3(9) . . . . ? C8 C9 C10A C11A 39.8(3) . . . . ? C9 C10A C11A C12 -62.4(4) . . . . ? C8 C9 C10B C11B -48(2) . . . . ? C9 C10B C11B C12 63(3) . . . . ? C10B C11B C12 C13 -41(2) . . . . ? C10A C11A C12 C13 49.9(3) . . . . ? C6 C8 C13 N4 0.18(19) . . . . ? C9 C8 C13 N4 -176.27(14) . . . . ? C6 C8 C13 C12 178.75(15) . . . . ? C9 C8 C13 C12 2.3(2) . . . . ? C11B C12 C13 N4 -171.9(13) . . . . ? C11A C12 C13 N4 157.1(2) . . . . ? C11B C12 C13 C8 9.7(13) . . . . ? C11A C12 C13 C8 -21.3(3) . . . . ? O2 C15 C16 C17 -178.44(17) . . . . ? N5 C15 C16 C17 1.3(2) . . . . ? C15 C16 C17 N6 -1.5(2) . . . . ? C15 C16 C17 C18 177.49(15) . . . . ? N7 C19 C21 C22 -0.32(17) . . . . ? C20 C19 C21 C22 -179.47(16) . . . . ? N7 C19 C21 C26 -179.57(16) . . . . ? C20 C19 C21 C26 1.3(3) . . . . ? C19 C21 C22 N8 0.39(19) . . . . ? C26 C21 C22 N8 179.71(15) . . . . ? C19 C21 C22 C23 -179.33(15) . . . . ? C26 C21 C22 C23 0.0(3) . . . . ? N8 C22 C23 C24 -167.08(16) . . . . ? C21 C22 C23 C24 12.6(2) . . . . ? C22 C23 C24 C25 -43.5(2) . . . . ? C23 C24 C25 C26 64.5(2) . . . . ? C19 C21 C26 C25 -163.48(17) . . . . ? C22 C21 C26 C25 17.4(2) . . . . ? C24 C25 C26 C21 -48.1(2) . . . . ? N2 C1 N1 C2 2.1(3) . . . . ? N3 C1 N1 C2 -177.38(14) . . . . ? O1 C2 N1 C1 179.72(16) . . . . ? C3 C2 N1 C1 -0.7(2) . . . . ? N1 C1 N2 C4 -0.9(2) . . . . ? N3 C1 N2 C4 178.54(13) . . . . ? C3 C4 N2 C1 -1.6(2) . . . . ? C5 C4 N2 C1 176.68(14) . . . . ? C8 C6 N3 N4 -0.31(17) . . . . ? C7 C6 N3 N4 179.40(14) . . . . ? C8 C6 N3 C1 -176.48(15) . . . . ? C7 C6 N3 C1 3.2(3) . . . . ? N2 C1 N3 C6 -2.3(3) . . . . ? N1 C1 N3 C6 177.22(14) . . . . ? N2 C1 N3 N4 -178.26(13) . . . . ? N1 C1 N3 N4 1.2(2) . . . . ? C8 C13 N4 N3 -0.35(17) . . . . ? C12 C13 N4 N3 -178.92(14) . . . . ? C6 N3 N4 C13 0.41(17) . . . . ? C1 N3 N4 C13 177.09(13) . . . . ? N6 C14 N5 C15 -0.3(3) . . . . ? N7 C14 N5 C15 179.35(14) . . . . ? O2 C15 N5 C14 179.30(15) . . . . ? C16 C15 N5 C14 -0.5(2) . . . . ? N5 C14 N6 C17 0.2(2) . . . . ? N7 C14 N6 C17 -179.42(13) . . . . ? C16 C17 N6 C14 0.7(2) . . . . ? C18 C17 N6 C14 -178.35(14) . . . . ? C21 C19 N7 N8 0.17(17) . . . . ? C20 C19 N7 N8 179.36(15) . . . . ? C21 C19 N7 C14 176.97(15) . . . . ? C20 C19 N7 C14 -3.8(3) . . . . ? N6 C14 N7 N8 175.66(14) . . . . ? N5 C14 N7 N8 -4.0(2) . . . . ? N6 C14 N7 C19 -1.0(3) . . . . ? N5 C14 N7 C19 179.37(15) . . . . ? C21 C22 N8 N7 -0.28(18) . . . . ? C23 C22 N8 N7 179.44(15) . . . . ? C19 N7 N8 C22 0.07(17) . . . . ? C14 N7 N8 C22 -177.18(13) . . . . ?