#------------------------------------------------------------------------------ #$Date: 2023-11-10 04:00:10 +0200 (Fri, 10 Nov 2023) $ #$Revision: 287506 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/76/7247695.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_7247695 loop_ _publ_author_name 'Atceken, Nurunnisa' 'Hemingway, Jack' 'Bull, Craig L.' 'Liu, Xiaojiao' 'Michalchuk, Adam A.L.' 'Konar, Sumit' 'Morrison, Carole' 'Pulham, Colin R.' _publ_section_title ; High-pressure Structural Studies and Pressure-induced Sensitisation of 3,4,5-trinitro-1H-pyrazole ; _journal_name_full 'Physical Chemistry Chemical Physics' _journal_paper_doi 10.1039/D3CP04526A _journal_year 2023 _chemical_formula_moiety '6(C3 N5 O6)' _chemical_formula_sum 'C18 N30 O36' _chemical_formula_weight 1212.48 _space_group_crystal_system monoclinic _space_group_IT_number 9 _space_group_name_Hall 'C -2yc' _space_group_name_H-M_alt 'C 1 c 1' _atom_sites_solution_primary dual _audit_block_doi 10.5517/ccdc.csd.cc29gp8r _audit_creation_date 2021-12-16 _audit_creation_method ; Olex2 1.3 (compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408) ; _audit_update_record ; 2021-12-16 deposited with the CCDC. 2023-11-08 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 127.623(5) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 19.319(2) _cell_length_b 7.5668(13) _cell_length_c 14.458(3) _cell_measurement_reflns_used 1713 _cell_measurement_temperature 287.2 _cell_measurement_theta_max 24.47 _cell_measurement_theta_min 2.86 _cell_volume 1674.0(5) _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 287.2 _diffrn_measured_fraction_theta_full 0.550 _diffrn_measured_fraction_theta_max 0.550 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0320 _diffrn_reflns_av_unetI/netI 0.0488 _diffrn_reflns_Laue_measured_fraction_full 0.550 _diffrn_reflns_Laue_measured_fraction_max 0.550 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 3579 _diffrn_reflns_point_group_measured_fraction_full 0.506 _diffrn_reflns_point_group_measured_fraction_max 0.505 _diffrn_reflns_theta_full 25.022 _diffrn_reflns_theta_max 25.022 _diffrn_reflns_theta_min 2.662 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.235 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_correction_T_min 0.6076 _exptl_absorpt_correction_type multi-scan _exptl_crystal_colour 'clear colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 2.405 _exptl_crystal_description block _exptl_crystal_F_000 1212 _refine_diff_density_max 0.227 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.062 _refine_ls_abs_structure_details ; Flack x determined using 539 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -2.4(10) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_hydrogen_treatment undef _refine_ls_matrix_type full _refine_ls_number_parameters 379 _refine_ls_number_reflns 1493 _refine_ls_number_restraints 317 _refine_ls_restrained_S_all 0.920 _refine_ls_R_factor_all 0.0522 _refine_ls_R_factor_gt 0.0416 _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^)+(0.0927P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1072 _refine_ls_wR_factor_ref 0.1137 _reflns_Friedel_coverage 0.836 _reflns_Friedel_fraction_full 0.461 _reflns_Friedel_fraction_max 0.461 _reflns_number_gt 1292 _reflns_number_total 1493 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3cp04526a2.cif _cod_data_source_block 2tnp_p10_h _cod_database_code 7247695 _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. ; _olex2_refinement_description ; 1. Restrained distances C00W-C00M \\sim C00W-C00I with sigma of 0.02 N4-C00M \\sim N00A-C00I with sigma of 0.02 C00M-N4 \\sim C00I-N00A with sigma of 0.02 C00I-N00A \\sim N4-C00M with sigma of 0.05 N4-C00M \\sim N9-C00V with sigma of 0.02 N00A-C00I \\sim N4-C00M with sigma of 0.1 C00W-C00I \\sim C00W-C00M with sigma of 0.1 2. Restrained planarity N00A, C00I, C00W, C00M, N4 with sigma of 0.1 3. Rigid body (RIGU) restrains All non-hydrogen atoms with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004 ; _shelx_res_file ; TITL 2tnp_p10_h_a.res in Cc 2tnp_p10_h.res created by SHELXL-2018/3 at 16:50:29 on 16-Dec-2021 REM Old TITL 2tnp_p10_h_a.res in Cc REM SHELXT solution in Cc: R1 0.232, Rweak 0.053, Alpha 0.082 REM 0.489 for 58 systematic absences, Orientation as input REM Flack x = -3.849 ( 6.442 ) from 552 Parsons' quotients REM Formula found by SHELXT: C19 N4 O12 CELL 0.71073 19.3191 7.5668 14.4583 90 127.623 90 ZERR 2 0.0021 0.0013 0.0027 0 0.005 0 LATT -7 SYMM +X,-Y,0.5+Z SFAC C N O UNIT 36 60 72 SADI C00W C00M C00W C00I SADI N4 C00M N00A C00I SADI C00M N4 C00I N00A SADI 0.05 C00I N00A N4 C00M SADI N4 C00M N9 C00V SADI 0.1 N00A C00I N4 C00M SADI 0.1 C00W C00I C00W C00M FLAT N00A C00I C00W C00M N4 RIGU L.S. 10 PLAN 20 TEMP 14.05 CONF list 4 MORE -1 fmap 2 53 acta OMIT 1 -5 -7 OMIT 1 5 -7 OMIT 0 -2 -2 OMIT 0 2 2 REM REM REM WGHT 0.092700 FVAR 0.51094 O001 3 0.291663 0.193453 0.429460 11.00000 0.03832 0.02568 = 0.04504 0.00270 0.03572 0.00577 N11 2 0.016057 0.698317 0.181697 11.00000 0.01892 0.03310 = 0.01349 0.00808 0.01262 0.00780 O003 3 0.625332 0.617282 0.535995 11.00000 0.02566 0.02062 = 0.02793 -0.00115 0.01334 -0.00822 O004 3 0.491386 -0.164229 0.456022 11.00000 0.02642 0.03665 = 0.03092 -0.00082 0.01158 0.00698 O005 3 0.820796 0.917617 0.891564 11.00000 0.04533 0.04286 = 0.03425 -0.01608 0.03399 -0.02001 N14 2 0.127740 0.897229 0.330171 11.00000 0.02021 0.01330 = 0.03173 -0.00115 0.01518 0.00511 O007 3 0.651927 0.804542 0.667759 11.00000 0.02362 0.05028 = 0.02576 -0.01152 0.01780 -0.00544 N2 2 0.343903 0.114335 0.424723 11.00000 0.02522 0.01728 = 0.03369 0.00614 0.02154 0.00051 O009 3 0.984783 1.025850 0.848926 11.00000 0.02554 0.02138 = 0.03135 -0.00858 0.01649 -0.00438 N00A 2 0.791911 0.630302 0.618762 11.00000 0.01333 0.03553 = 0.02921 -0.00716 0.01077 0.00043 C9 1 0.497421 0.134423 0.487136 11.00000 0.02765 0.02611 = 0.01616 0.00323 0.01591 -0.00213 O12 3 0.329826 0.521502 0.576952 11.00000 0.02972 0.02717 = 0.02983 0.00438 0.02293 0.00588 O13 3 0.351566 0.792757 0.639462 11.00000 0.02055 0.02114 = 0.03284 -0.00786 0.01223 -0.00194 O00E 3 0.151544 0.362549 0.277101 11.00000 0.03812 0.04284 = 0.01805 -0.01244 0.01675 -0.00303 O00F 3 0.169788 0.339877 0.438940 11.00000 0.02030 0.04835 = 0.02381 0.00528 0.01249 -0.00665 N8 2 0.500418 -0.013542 0.428652 11.00000 0.01932 0.03193 = 0.01807 -0.00746 0.00919 0.00259 N7 2 0.672660 0.714402 0.620484 11.00000 0.02042 0.03086 = 0.02338 -0.00278 0.01518 -0.00911 C00I 1 0.761599 0.725026 0.664743 11.00000 0.01127 0.02055 = 0.01733 0.00275 0.00674 -0.00325 O00J 3 -0.006108 0.545180 0.154525 11.00000 0.02290 0.02967 = 0.01873 -0.00094 0.01160 0.00132 N4 2 0.874326 0.666601 0.664645 11.00000 0.02246 0.01954 = 0.03434 -0.00991 0.01686 -0.01179 N3 2 0.159275 0.430145 0.361241 11.00000 0.01388 0.02929 = 0.01624 -0.00104 0.00842 -0.00137 C00M 1 0.892855 0.797560 0.740007 11.00000 0.01215 0.00705 = 0.02453 0.00700 0.01081 0.00782 N1 2 0.650051 0.244649 0.604344 11.00000 0.01961 0.02691 = 0.02201 0.01091 0.01269 0.00727 C00O 1 0.427988 0.193427 0.480940 11.00000 0.02483 0.04098 = 0.01230 0.00167 0.01367 0.00233 N6 2 0.974356 0.887218 0.796626 11.00000 0.00906 0.02522 = 0.00895 -0.00107 0.00163 -0.00042 C00Q 1 0.227157 0.721595 0.459538 11.00000 0.02029 0.02497 = 0.01517 0.00092 0.01431 0.00009 O17 3 0.824137 1.120682 0.787869 11.00000 0.02831 0.03169 = 0.02819 -0.00810 0.01668 0.00210 O11 3 0.330259 -0.028925 0.372233 11.00000 0.03369 0.03440 = 0.03398 -0.01247 0.01971 -0.00242 C10 1 0.164088 0.613823 0.372360 11.00000 0.01804 0.01865 = 0.01516 0.00312 0.01102 0.00391 O00U 3 0.669205 0.109493 0.573741 11.00000 0.02242 0.04694 = 0.02434 -0.00284 0.01663 0.00253 C00V 1 0.560490 0.255013 0.558318 11.00000 0.02182 0.02479 = 0.02234 -0.00010 0.01731 0.00053 C00W 1 0.826045 0.833654 0.746509 11.00000 0.00440 0.02722 = 0.00432 0.00440 -0.00240 0.00585 O15 3 -0.025752 0.833297 0.127138 11.00000 0.02561 0.03465 = 0.03807 0.01775 0.01729 0.00623 O10 3 0.703203 0.357355 0.672776 11.00000 0.02630 0.02985 = 0.03325 0.00147 0.01386 0.00054 O14 3 1.024459 0.830581 0.778343 11.00000 0.01544 0.02728 = 0.02919 0.00270 0.01619 0.00000 N10 2 0.450787 0.334955 0.544102 11.00000 0.01895 0.04124 = 0.01296 0.00207 0.00915 0.00733 N9 2 0.534145 0.379573 0.595304 11.00000 0.02312 0.03066 = 0.02351 0.00825 0.01479 0.00959 N15 2 0.823572 0.969087 0.813911 11.00000 0.01362 0.02916 = 0.03088 -0.00668 0.01606 -0.00858 O16 3 0.510003 0.020529 0.353067 11.00000 0.03274 0.07398 = 0.03427 -0.00763 0.02777 -0.01049 N12 2 0.309495 0.674997 0.568458 11.00000 0.01719 0.02225 = 0.02604 0.00039 0.01700 -0.00095 C12 1 0.101851 0.733249 0.292086 11.00000 0.02321 0.01927 = 0.01312 0.00153 0.01322 0.00592 N13 2 0.207317 0.891972 0.437308 11.00000 0.02335 0.01665 = 0.02580 0.00213 0.01473 0.00896 HKLF 4 REM 2tnp_p10_h_a.res in Cc REM wR2 = 0.1137, GooF = S = 1.017, Restrained GooF = 0.920 for all data REM R1 = 0.0416 for 1292 Fo > 4sig(Fo) and 0.0522 for all 1493 data REM 379 parameters refined using 317 restraints END WGHT 0.0925 0.0000 REM Highest difference peak 0.227, deepest hole -0.259, 1-sigma level 0.062 Q1 1 -0.0975 0.7577 0.0070 11.00000 0.05 0.23 Q2 1 0.6089 0.7689 0.4715 11.00000 0.05 0.23 Q3 1 0.1209 0.1318 0.2605 11.00000 0.05 0.22 Q4 1 0.5745 0.6587 0.4244 11.00000 0.05 0.21 Q5 1 0.1816 0.7330 0.3401 11.00000 0.05 0.20 Q6 1 0.1821 0.2452 0.4286 11.00000 0.05 0.20 Q7 1 0.4066 0.3941 0.5397 11.00000 0.05 0.20 Q8 1 0.3591 0.8983 0.5242 11.00000 0.05 0.20 Q9 1 0.7006 0.4812 0.7213 11.00000 0.05 0.19 Q10 1 -0.0370 0.9329 0.1919 11.00000 0.05 0.19 Q11 1 0.5562 0.4990 0.5018 11.00000 0.05 0.19 Q12 1 0.7381 0.7845 0.8370 11.00000 0.05 0.19 Q13 1 0.2834 1.0197 0.4814 11.00000 0.05 0.18 Q14 1 0.6204 0.0028 0.5743 11.00000 0.05 0.18 Q15 1 0.8337 0.7146 0.9592 11.00000 0.05 0.18 Q16 1 0.2172 0.5050 0.3050 11.00000 0.05 0.18 Q17 1 0.4536 -0.2714 0.4807 11.00000 0.05 0.18 Q18 1 0.0808 0.4414 0.2172 11.00000 0.05 0.18 Q19 1 0.0798 0.7227 0.3789 11.00000 0.05 0.18 Q20 1 0.1244 0.2337 0.2825 11.00000 0.05 0.18 ; _shelx_res_checksum 28772 _shelx_hkl_file ; -2 0 2 63.39 3.30 2 0 -2 59.49 3.10 -4 0 4 3405.76 115.59 4 0 -4 3439.56 115.99 -6 0 6 559.44 21.00 6 0 -6 566.54 20.60 6 0 -6 538.75 20.80 -6 0 6 550.44 22.30 6 0 -6 546.75 22.10 -8 0 8 127.89 9.90 8 0 -8 100.89 8.10 -8 0 8 132.19 12.50 5 1 -5 1543.85 53.89 5 1 -5 1573.44 54.29 5 1 -5 1587.44 54.89 -5 -1 5 1516.65 53.29 -5 -1 5 1522.65 52.09 7 1 -7 1266.27 46.50 7 1 -7 1280.37 45.80 7 1 -7 1273.67 45.20 -7 -1 7 1284.77 45.10 -7 -1 7 1233.28 46.10 9 1 -9 366.86 17.90 9 1 -9 341.67 17.30 9 1 -9 376.66 19.50 -9 -1 9 333.77 17.60 -9 -1 9 376.16 19.80 11 1 -11 271.77 17.00 -11 -1 11 286.87 21.30 -13 -1 13 210.88 22.70 4 2 -4 869.01 30.50 4 2 -4 833.42 30.00 4 2 -4 797.02 29.70 4 2 -4 813.42 30.50 -4 -2 4 807.72 30.10 -4 -2 4 835.72 29.70 -4 -2 4 823.72 29.00 6 2 -6 2356.06 80.69 6 2 -6 2319.57 80.39 6 2 -6 2347.86 80.39 6 2 -6 2311.27 81.29 -6 -2 6 2364.06 80.39 -6 -2 6 2282.87 80.19 8 2 -8 358.16 15.90 8 2 -8 344.87 16.40 8 2 -8 358.06 18.70 8 2 -8 307.27 22.40 8 2 -8 372.46 17.00 -8 -2 8 335.97 18.80 -8 -2 8 321.57 17.00 -8 -2 8 355.96 15.40 10 2 -10 10.80 7.70 10 2 -10 12.00 6.40 10 2 -10 13.30 7.20 -10 -2 10 6.60 9.30 -10 -2 10 2.60 7.80 12 2 -12 32.10 8.90 12 2 -12 56.99 10.60 12 2 -12 44.40 10.00 -12 -2 12 39.80 11.10 -12 -2 12 37.20 12.90 14 2 -14 37.50 11.20 14 2 -14 58.79 10.80 14 2 -14 32.70 11.90 -14 -2 14 45.70 14.90 -14 -2 14 55.09 13.30 16 2 -16 17.50 12.40 -16 -2 16 39.80 14.80 -16 -2 16 48.60 16.90 5 3 -5 588.64 23.10 5 3 -5 569.64 22.80 5 3 -5 601.54 23.60 5 3 -5 591.94 24.60 -5 -3 5 555.14 24.20 -5 -3 5 547.75 24.30 -5 -3 5 547.65 21.90 -5 -3 5 572.14 21.30 -5 -3 5 546.65 22.20 7 3 -7 190.08 14.80 7 3 -7 183.18 12.00 7 3 -7 172.78 12.90 7 3 -7 161.08 16.60 -7 -3 7 171.78 12.40 9 3 -9 276.07 17.00 9 3 -9 243.68 17.40 9 3 -9 254.27 16.20 -9 -3 9 226.78 13.70 -9 -3 9 234.08 17.60 -9 -3 9 218.98 15.50 11 3 -11 56.89 10.10 11 3 -11 38.30 9.80 -11 -3 11 45.60 9.10 -11 -3 11 49.10 11.50 13 3 -13 39.70 11.50 13 3 -13 46.90 11.70 -13 -3 13 42.20 12.90 15 3 -15 52.59 13.50 15 3 -15 48.50 15.80 -15 -3 15 46.50 15.80 6 4 -6 598.94 25.00 6 4 -6 563.74 26.50 -6 -4 6 592.44 24.90 -6 -4 6 579.54 24.40 -6 -4 6 574.74 23.30 8 4 -8 279.37 16.90 -8 -4 8 247.28 17.10 10 4 -10 205.78 17.50 10 4 -10 182.28 14.00 10 4 -10 188.58 14.90 -10 -4 10 189.48 15.40 -10 -4 10 193.78 18.20 12 4 -12 329.07 24.00 12 4 -12 403.06 25.30 -12 -4 12 349.17 21.80 14 4 -14 216.58 33.10 9 5 -9 10.50 10.00 -9 -5 9 12.20 9.60 11 5 -11 155.78 14.80 11 5 -11 144.29 15.60 11 5 -11 164.48 15.50 -11 -5 11 147.99 13.70 -11 -5 11 153.58 15.80 13 5 -13 8.00 16.70 13 5 -13 21.50 23.80 -10 0 9 2.70 7.40 -10 0 9 0.50 5.70 10 0 -9 1.20 4.90 10 0 -9 -1.70 6.30 10 0 -9 3.00 4.70 -10 0 9 4.20 5.40 10 0 -9 1.80 5.50 -8 0 7 1.00 4.70 8 0 -7 4.80 5.40 8 0 -7 2.10 4.10 -8 0 7 1.00 5.70 8 0 -7 8.80 4.20 8 0 -7 -0.10 3.50 -8 0 7 -2.40 4.10 6 0 -5 1.60 2.30 6 0 -5 2.60 2.90 -6 0 5 2.10 2.50 6 0 -5 -0.30 2.30 -6 0 5 -1.20 3.50 4 0 -3 0.30 1.30 -4 0 3 1.00 1.30 4 0 -3 -0.40 1.10 -4 0 3 0.20 1.70 4 0 -3 0.40 1.40 2 0 -1 0.00 0.40 -2 0 1 0.20 0.30 -2 0 1 1.10 0.50 2 0 -1 0.00 0.40 -2 0 1 0.30 0.50 -2 0 1 0.30 0.40 2 0 -1 0.20 0.40 2 0 -1 0.70 0.40 0 0 -1 0.80 0.70 0 0 1 0.10 0.70 0 0 -1 0.00 0.60 0 0 1 -0.10 0.70 -2 0 3 -0.40 1.10 -2 0 3 -0.10 1.30 -4 0 5 0.60 2.30 4 0 -5 2.30 2.40 4 0 -5 -0.30 2.60 -4 0 5 0.00 2.70 13 1 -12 25.50 8.90 -13 -1 12 4.30 11.00 11 1 -10 21.50 6.90 -11 -1 10 29.50 9.30 9 1 -8 334.77 17.60 9 1 -8 339.97 16.10 9 1 -8 320.97 15.60 -9 -1 8 326.67 17.80 7 1 -6 371.36 15.30 7 1 -6 376.36 16.70 7 1 -6 364.86 15.50 -7 -1 6 350.86 14.40 5 1 -4 1114.79 39.10 5 1 -4 1140.79 39.80 5 1 -4 1109.99 38.80 5 1 -4 1138.69 39.40 -5 -1 4 1059.89 37.80 -5 -1 4 1105.79 38.40 3 1 -2 352.46 13.10 3 1 -2 366.16 13.20 -3 -1 2 357.26 13.10 1 1 -2 64.59 4.10 1 1 -2 63.29 4.00 1 1 -2 63.49 3.20 1 1 -2 53.59 3.00 1 1 -2 56.79 3.40 1 1 -2 71.99 4.80 -1 -1 2 60.19 9.80 -1 -1 2 59.29 3.10 -1 -1 2 55.19 2.80 -1 -1 2 57.29 4.00 -1 -1 2 49.60 2.80 -1 -1 2 55.19 2.60 -1 -1 2 62.49 3.90 3 1 -4 202.88 8.20 3 1 -4 219.18 9.90 3 1 -4 206.38 8.70 3 1 -4 214.48 10.30 3 1 -4 202.38 8.50 -3 -1 4 210.98 9.20 -3 -1 4 203.18 8.10 -3 -1 4 196.18 8.40 -3 -1 4 193.58 9.10 5 1 -6 1199.48 44.40 5 1 -6 1211.98 42.70 5 1 -6 1229.88 43.80 5 1 -6 1230.98 43.20 -5 -1 6 1143.29 40.00 -5 -1 6 1001.00 41.10 -5 -1 6 1159.38 39.20 7 1 -8 1231.58 43.40 7 1 -8 1181.58 42.70 7 1 -8 1146.79 44.10 -7 -1 8 1200.78 44.00 -7 -1 8 1190.78 42.70 -7 -1 8 1143.89 44.30 9 1 -10 222.68 14.60 -9 -1 10 224.08 17.20 11 1 -12 242.78 17.90 -11 -1 12 276.67 22.00 16 2 -15 49.70 14.70 16 2 -15 72.09 13.80 16 2 -15 44.20 22.50 -16 -2 15 69.19 19.20 -16 -2 15 67.19 22.50 14 2 -13 13.10 9.80 14 2 -13 17.60 10.40 14 2 -13 18.70 9.40 -14 -2 13 11.70 11.00 -14 -2 13 19.20 12.80 12 2 -11 532.55 25.20 12 2 -11 512.95 24.00 12 2 -11 541.35 25.80 -12 -2 11 520.35 28.30 -12 -2 11 467.05 25.60 10 2 -9 233.38 14.90 10 2 -9 230.48 14.00 10 2 -9 239.38 14.90 -10 -2 9 212.38 13.50 -10 -2 9 219.48 15.80 -10 -2 9 237.58 18.30 8 2 -7 122.79 10.50 8 2 -7 131.59 12.10 8 2 -7 135.09 10.10 8 2 -7 136.09 9.90 8 2 -7 122.69 8.70 8 2 -7 154.38 12.40 -8 -2 7 131.99 11.50 -8 -2 7 126.49 12.40 -8 -2 7 121.79 9.00 -8 -2 7 136.69 10.30 6 2 -5 696.63 25.70 6 2 -5 682.13 26.60 6 2 -5 658.33 25.60 -6 -2 5 631.94 24.60 -6 -2 5 635.34 24.10 4 2 -3 3860.31 126.39 4 2 -3 3698.93 126.19 4 2 -3 3618.04 125.89 -4 -2 3 4039.80 135.99 -4 -2 3 4001.80 136.19 2 2 -3 1319.57 49.80 2 2 -3 1299.07 46.10 2 2 -3 1320.17 45.30 2 2 -3 1327.17 46.10 2 2 -3 1272.17 45.00 -2 -2 3 1342.57 48.60 -2 -2 3 1354.66 46.60 -2 -2 3 1312.97 47.60 -2 -2 3 1371.06 47.30 4 2 -5 1.70 5.10 4 2 -5 -0.80 5.50 4 2 -5 2.70 2.80 4 2 -5 3.30 3.20 4 2 -5 -2.20 3.40 -4 -2 5 -0.10 5.10 -4 -2 5 3.50 3.30 -4 -2 5 4.20 3.50 6 2 -7 5.20 5.00 6 2 -7 2.80 4.50 6 2 -7 0.50 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-18 -2 6 4.40 6.90 18 -2 -6 12.00 7.40 18 -2 -6 10.20 6.70 -18 -2 6 -0.20 7.90 16 2 -4 -2.80 7.40 -16 -2 4 8.80 7.50 16 -2 -4 5.30 5.90 16 -2 -4 0.00 5.30 -14 2 2 173.38 18.00 -14 2 2 143.99 17.00 -14 2 2 185.08 22.00 14 -2 -2 183.68 23.70 -12 2 0 315.77 25.80 -12 2 0 325.87 30.70 12 -2 0 362.26 28.90 -10 2 -2 202.78 24.40 10 -2 2 229.98 24.20 10 -2 2 128.69 72.99 -8 2 -4 76.39 17.20 -8 2 -4 42.10 21.70 8 -2 4 15.60 47.10 -6 2 -6 196.18 20.00 -6 2 -6 214.78 23.20 6 -2 6 314.57 36.70 -4 2 -8 241.08 21.80 -4 2 -8 254.97 30.30 4 -2 8 242.08 28.60 -2 2 -10 354.46 32.20 -2 2 -10 339.47 37.10 2 -2 10 253.27 31.10 21 3 -9 64.79 11.70 -21 -3 9 55.29 10.90 19 3 -7 10.90 9.20 -19 -3 7 -1.60 7.50 -19 -3 7 4.60 9.20 -15 3 3 244.58 23.40 15 -3 -3 326.37 32.90 -13 3 1 259.37 24.60 13 -3 -1 311.47 31.30 -11 3 -1 82.09 17.30 -11 3 -1 108.99 27.50 -11 3 -1 96.09 23.30 11 -3 1 97.79 23.80 11 -3 1 97.49 28.50 -9 3 -3 264.57 33.80 -9 3 -3 241.38 25.70 -9 3 -3 261.97 29.10 9 -3 3 265.47 25.00 9 -3 3 241.18 26.90 -7 3 -5 12.40 21.50 -7 3 -5 16.60 17.80 7 -3 5 13.30 15.70 -5 3 -7 70.99 22.60 -5 3 -7 66.59 19.50 5 -3 7 73.49 51.69 -3 3 -9 256.87 27.60 -3 3 -9 257.77 33.10 3 -3 9 348.77 63.79 -1 3 -11 505.05 42.20 -1 3 -11 556.54 59.59 1 -3 11 522.05 70.49 1 3 -13 38.50 25.20 1 3 -13 75.19 35.20 -1 -3 13 21.10 54.59 -12 4 0 250.77 25.60 12 -4 0 310.37 33.00 -8 4 -4 33.50 18.20 -8 4 -4 58.49 26.10 -8 4 -4 68.49 23.60 8 -4 4 44.20 25.50 8 -4 4 51.69 19.50 -6 4 -6 116.59 33.00 -6 4 -6 105.29 22.50 6 -4 6 135.29 23.50 -4 4 -8 130.99 30.30 -4 4 -8 130.39 25.10 4 -4 8 121.19 22.20 -2 4 -10 251.37 46.10 0 4 -12 19.90 34.80 0 4 -12 32.20 25.80 -7 5 -5 -3.50 20.20 -7 5 -5 3.10 21.50 7 -5 5 12.00 20.70 -5 5 -7 21.60 24.50 -5 5 -7 2.00 21.70 -5 5 -7 19.30 39.20 5 -5 7 6.70 25.50 5 -5 7 11.00 27.10 -3 5 -9 52.79 40.60 -3 5 -9 15.80 22.80 3 -5 9 3.20 26.40 -4 6 -8 68.39 30.80 4 -6 8 39.60 38.10 4 -6 8 48.80 33.90 22 0 -9 5.90 10.00 22 0 -9 -4.90 9.40 20 0 -7 -3.30 9.00 18 0 -5 -5.60 7.40 18 0 -5 1.80 5.70 18 0 -5 4.80 6.70 18 0 -5 -1.50 7.20 16 0 -3 2.50 6.60 16 0 -3 -2.30 6.00 -12 0 -1 -5.60 14.20 -12 0 -1 -24.80 12.10 10 0 3 -34.20 22.90 -21 1 8 161.58 15.30 21 1 -8 180.48 14.40 21 1 -8 164.78 13.80 21 -1 -8 132.09 13.60 19 1 -6 4.30 8.10 19 1 -6 13.70 9.30 19 -1 -6 0.00 7.60 17 1 -4 56.29 8.10 17 1 -4 60.09 9.80 -17 -1 4 68.49 7.80 17 -1 -4 55.59 7.20 17 -1 -4 55.19 6.90 15 1 -2 363.26 19.10 15 1 -2 365.66 17.90 -15 1 2 311.87 24.20 -15 -1 2 375.66 17.80 -13 1 0 3092.89 114.39 13 1 0 3090.79 111.99 -13 1 0 3445.66 122.49 13 1 0 3128.19 107.49 -13 -1 0 3199.08 108.99 -13 -1 0 3318.37 109.89 -13 -1 0 2987.50 114.29 -11 1 -2 497.15 43.90 11 -1 2 234.48 62.19 -9 1 -4 151.18 21.90 9 -1 4 146.99 32.60 -7 1 -6 29.90 16.80 -7 1 -6 22.50 24.20 7 -1 6 44.90 23.00 22 2 -9 54.69 11.80 22 2 -9 38.80 11.10 20 2 -7 159.28 13.20 -20 -2 7 175.58 15.10 18 -2 -5 301.17 16.90 -18 -2 5 281.97 18.40 -18 -2 5 285.77 19.30 -14 2 1 1.80 13.90 -12 2 -1 125.39 19.00 -12 2 -1 103.09 24.20 12 -2 1 146.99 19.50 -10 2 -3 1383.36 67.09 -10 2 -3 1305.37 60.29 10 -2 3 1687.93 143.29 -8 2 -5 75.49 16.00 -8 2 -5 94.19 23.90 -8 2 -5 118.29 19.60 8 -2 5 55.69 47.60 8 -2 5 92.19 23.10 -6 2 -7 85.29 21.20 -6 2 -7 60.19 25.10 -6 2 -7 69.99 17.40 6 -2 7 99.99 55.39 6 -2 7 56.79 23.70 -4 2 -9 192.28 21.80 -4 2 -9 148.79 28.20 4 -2 9 166.68 28.40 2 -2 11 222.98 31.80 -21 -3 8 435.36 23.50 -15 3 2 99.89 22.50 15 -3 -2 76.09 23.90 -13 3 0 924.41 60.09 -13 3 0 925.61 49.50 -13 3 0 1002.30 47.10 13 -3 0 1119.29 58.19 13 -3 0 1050.19 51.39 -11 3 -2 21.20 16.60 -11 3 -2 20.40 27.10 11 -3 2 -6.70 19.00 -9 3 -4 146.79 21.70 -9 3 -4 141.79 26.30 9 -3 4 147.69 20.30 -7 3 -6 37.80 20.40 -7 3 -6 34.40 22.80 7 -3 6 11.80 52.59 -5 3 -8 288.17 34.80 -5 3 -8 341.97 35.90 5 -3 8 565.54 107.79 -3 3 -10 43.80 24.00 -3 3 -10 49.10 32.60 3 -3 10 9.70 53.29 -1 3 -12 37.50 34.80 -1 3 -12 21.10 25.20 1 -3 12 10.30 52.09 -12 4 -1 44.00 21.20 12 -4 1 29.70 20.90 -10 4 -3 577.44 38.80 -10 4 -3 550.24 42.40 -10 4 -3 511.45 54.89 10 -4 3 650.33 49.10 10 -4 3 626.74 41.60 -8 4 -5 -20.50 18.80 -8 4 -5 22.40 31.90 8 -4 5 -23.10 20.50 -6 4 -7 -9.70 25.30 -6 4 -7 15.40 21.00 6 -4 7 12.00 19.30 -4 4 -9 20.30 24.90 -4 4 -9 40.80 31.10 -2 4 -11 62.39 35.70 -2 4 -11 23.20 25.60 -9 5 -4 40.30 22.00 -9 5 -4 24.80 23.00 9 -5 4 9.30 22.30 -7 5 -6 17.20 27.20 -7 5 -6 62.09 28.20 -7 5 -6 49.30 39.40 7 -5 6 52.99 26.60 7 -5 6 50.39 25.70 -5 5 -8 249.38 38.70 -5 5 -8 249.68 29.00 5 -5 8 219.88 28.20 22 0 -8 20.60 9.50 22 0 -8 15.10 9.70 20 0 -6 149.29 12.10 20 0 -6 148.79 11.90 18 0 -4 51.89 8.40 18 0 -4 55.29 9.50 -14 0 0 6.20 14.30 -12 0 -2 316.67 27.20 12 0 2 284.27 27.80 21 1 -7 4.90 8.30 21 1 -7 -8.80 8.40 21 -1 -7 -6.90 8.00 19 1 -5 52.29 9.10 19 -1 -5 58.89 8.20 19 -1 -5 52.99 7.60 17 1 -3 239.08 17.10 17 1 -3 248.38 15.40 -17 -1 3 249.58 14.30 15 1 -1 383.86 19.20 -15 -1 1 424.66 19.90 -13 1 -1 71.79 17.10 -13 1 -1 71.49 24.50 -11 1 -3 14.70 14.60 -11 1 -3 -0.20 20.90 -11 1 -3 -4.40 16.50 11 -1 3 -2.80 19.70 -9 1 -5 924.71 58.79 -9 1 -5 868.51 44.00 9 -1 5 846.02 52.69 -7 1 -7 -13.20 16.10 7 -1 7 -7.80 22.00 22 2 -8 72.09 11.90 20 2 -6 5.60 8.40 -20 -2 6 6.90 7.60 -16 2 2 398.16 37.10 -14 2 0 257.17 36.00 -14 2 0 244.18 22.60 -12 2 -2 25.20 17.30 -12 2 -2 2.60 21.80 -10 2 -4 477.75 47.90 -10 2 -4 534.65 36.60 10 -2 4 548.85 104.79 -8 2 -6 1.80 24.90 -8 2 -6 32.10 16.70 -8 2 -6 29.20 19.50 8 -2 6 31.30 50.69 8 -2 6 25.70 22.80 -6 2 -8 21.00 21.50 -6 2 -8 11.10 24.40 -6 2 -8 29.70 17.80 6 -2 8 6.10 23.30 6 -2 8 38.40 58.29 -4 2 -10 184.38 30.40 4 -2 10 121.19 33.40 -17 3 3 134.49 24.60 17 -3 -3 165.38 28.00 -15 3 1 10.50 29.10 -15 3 1 -4.50 22.30 15 -3 -1 -2.70 21.90 15 -3 -1 -19.50 24.00 -13 3 -1 341.07 37.90 -13 3 -1 378.86 32.50 13 -3 1 332.77 28.80 -11 3 -3 111.69 27.80 -11 3 -3 138.09 22.50 11 -3 3 176.38 22.60 -9 3 -5 434.46 46.20 -9 3 -5 331.87 36.40 -7 3 -7 49.30 26.00 -7 3 -7 31.40 20.50 7 -3 7 26.70 55.39 -5 3 -9 26.10 52.39 -3 3 -11 40.00 25.10 -3 3 -11 27.60 30.50 3 -3 11 16.10 51.59 -14 4 0 18.30 22.20 14 -4 0 29.10 23.20 -12 4 -2 -10.50 32.40 -12 4 -2 23.20 23.80 -12 4 -2 31.50 20.70 12 -4 2 20.40 21.00 12 -4 2 -3.00 24.10 -10 4 -4 34.20 20.60 -10 4 -4 30.60 31.10 10 -4 4 28.40 22.30 -8 4 -6 -18.30 25.80 -8 4 -6 26.70 21.80 8 -4 6 11.00 20.30 -6 4 -8 33.50 23.90 -4 4 -10 9.90 33.40 -4 4 -10 29.90 25.90 -9 5 -5 245.38 30.00 -9 5 -5 195.08 51.79 -9 5 -5 194.78 41.60 9 -5 5 224.18 32.90 9 -5 5 236.78 35.20 -7 5 -7 49.80 24.90 -7 5 -7 50.59 34.20 7 -5 7 22.00 22.90 22 0 -7 -8.50 8.60 22 0 -7 -1.50 8.20 20 0 -5 7.70 7.60 -14 0 -1 -19.80 13.40 12 0 3 3.80 21.00 -12 0 -3 25.20 15.20 21 1 -6 548.35 26.50 19 1 -4 189.88 16.00 -19 -1 4 184.58 19.80 17 1 -2 9.40 6.70 17 1 -2 2.20 7.10 -17 -1 2 -2.50 6.80 -17 -1 2 -0.80 5.70 -15 1 0 52.99 17.50 -13 1 -2 139.59 27.90 -13 1 -2 155.78 21.20 -11 1 -4 20.20 25.30 -11 1 -4 19.90 19.20 -11 1 -4 25.70 16.20 11 -1 4 39.50 23.10 -9 1 -6 32.60 17.90 9 -1 6 39.10 25.20 -16 2 1 336.27 30.50 -14 2 -1 39.60 26.50 -14 2 -1 46.50 19.30 -12 2 -3 98.79 27.70 -12 2 -3 92.39 20.70 12 -2 3 160.48 61.69 -10 2 -5 32.80 20.70 -10 2 -5 20.70 26.60 10 -2 5 26.20 54.49 -8 2 -7 143.69 20.80 -8 2 -7 129.39 28.70 -8 2 -7 113.39 23.30 8 -2 7 158.28 28.70 8 -2 7 96.69 54.79 -6 2 -9 129.89 27.10 -6 2 -9 100.49 30.70 -6 2 -9 96.79 33.00 6 -2 9 154.38 36.30 6 -2 9 176.78 103.19 -15 3 0 69.79 20.30 -15 3 0 66.49 28.70 15 -3 0 39.10 20.40 -13 3 -2 12.70 18.90 -13 3 -2 12.70 25.40 13 -3 2 -6.90 19.10 -11 3 -4 95.39 27.60 -11 3 -4 118.29 23.40 -9 3 -6 59.99 28.30 -9 3 -6 118.49 24.40 -7 3 -8 320.87 48.90 -7 3 -8 373.66 38.40 7 -3 8 476.35 79.79 -5 3 -10 133.49 35.20 -5 3 -10 155.18 28.90 5 -3 10 211.18 69.19 -14 4 -1 46.20 26.40 -14 4 -1 53.19 34.60 14 -4 1 25.90 25.30 14 -4 1 49.60 28.20 -12 4 -3 55.59 33.30 -12 4 -3 53.49 23.00 12 -4 3 71.49 21.90 -10 4 -5 18.40 33.80 -10 4 -5 20.50 35.40 10 -4 5 13.30 23.20 -8 4 -7 -5.70 28.80 -8 4 -7 14.20 23.60 -11 5 -4 195.68 28.30 -11 5 -4 133.19 30.80 -11 5 -4 161.28 41.80 11 -5 4 192.08 32.50 11 -5 4 149.39 29.80 -14 0 -2 154.48 19.00 -15 1 -1 -8.20 16.70 -15 1 -1 13.00 26.30 -13 1 -3 60.29 17.30 -13 1 -3 71.39 27.30 -13 1 -3 81.29 20.10 13 -1 3 74.49 23.80 -11 1 -5 475.05 35.60 11 -1 5 555.24 46.70 -16 2 0 110.29 20.60 -14 2 -2 15.60 27.80 -14 2 -2 35.10 20.60 -12 2 -4 116.39 22.60 -12 2 -4 137.49 31.10 12 -2 4 110.19 63.09 -10 2 -6 81.49 24.40 -10 2 -6 104.19 29.40 10 -2 6 65.19 58.79 -8 2 -8 4.60 19.60 -8 2 -8 14.80 22.80 8 -2 8 19.40 54.79 8 -2 8 22.50 25.80 -15 3 -1 158.18 23.80 -15 3 -1 145.39 32.30 -13 3 -3 121.59 30.80 -13 3 -3 123.09 24.40 -11 3 -5 56.49 25.80 -11 3 -5 73.99 40.00 -9 3 -7 35.80 23.70 -9 3 -7 -25.80 29.50 9 -3 7 -11.90 60.69 -16 4 0 32.20 33.50 16 -4 0 19.50 24.90 14 -4 2 38.10 39.10 -12 4 -4 164.48 26.80 -12 4 -4 173.18 49.80 12 -4 4 147.59 29.70 -10 4 -6 29.20 30.20 -10 4 -6 30.00 23.90 -16 0 -1 -31.30 16.30 -17 1 0 57.39 19.30 -15 1 -2 23.20 19.30 -13 1 -4 168.28 21.90 -13 1 -4 180.08 24.90 13 -1 4 195.68 29.50 13 -1 4 197.78 60.19 -18 2 1 28.60 19.20 -14 2 -3 293.67 39.20 -14 2 -3 289.97 29.10 -12 2 -5 140.69 28.80 12 -2 5 110.09 102.09 -10 2 -7 16.00 29.30 -10 2 -7 36.90 24.30 10 -2 7 -4.50 57.69 -17 3 0 182.08 24.60 -17 3 0 139.19 35.70 -15 3 -2 181.48 35.30 -15 3 -2 146.99 24.10 -13 3 -4 255.77 29.20 -13 3 -4 203.38 42.20 -11 3 -6 26.20 24.50 -11 3 -6 1.50 30.90 -17 1 -1 21.70 19.50 -15 1 -3 9.70 21.00 -16 2 -2 64.69 23.10 -16 2 -2 91.49 33.40 0 0 0 0.00 0.00 _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' ; _shelx_hkl_checksum 25486 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -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 O001 O 0.2917(6) 0.1935(16) 0.4295(8) 0.030(3) Uani 1 1 d . . . . . N11 N 0.0161(7) 0.698(2) 0.1817(9) 0.020(4) Uani 1 1 d . . . . . O003 O 0.6253(5) 0.6173(17) 0.5360(7) 0.027(3) Uani 1 1 d . . . . . O004 O 0.4914(7) -0.1642(19) 0.4560(9) 0.035(4) Uani 1 1 d . . . . . O005 O 0.8208(6) 0.9176(18) 0.8916(8) 0.035(3) Uani 1 1 d . . . . . N14 N 0.1277(6) 0.897(2) 0.3302(9) 0.022(3) Uani 1 1 d . . . . . O007 O 0.6519(5) 0.8045(16) 0.6678(7) 0.031(3) Uani 1 1 d . . . . . N2 N 0.3439(8) 0.114(2) 0.4247(11) 0.023(3) Uani 1 1 d . . . . . O009 O 0.9848(6) 1.0258(18) 0.8489(9) 0.027(3) Uani 1 1 d . . . . . N00A N 0.7919(6) 0.6303(19) 0.6188(9) 0.027(4) Uani 1 1 d D . . . . C9 C 0.4974(8) 0.134(2) 0.4871(11) 0.022(3) Uani 1 1 d . . . . . O12 O 0.3298(6) 0.5215(19) 0.5770(8) 0.026(3) Uani 1 1 d . . . . . O13 O 0.3516(5) 0.7928(17) 0.6395(8) 0.027(3) Uani 1 1 d . . . . . O00E O 0.1515(6) 0.3625(17) 0.2771(7) 0.033(3) Uani 1 1 d . . . . . O00F O 0.1698(5) 0.3399(18) 0.4389(7) 0.031(3) Uani 1 1 d . . . . . N8 N 0.5004(7) -0.014(2) 0.4287(10) 0.025(4) Uani 1 1 d . . . . . N7 N 0.6727(7) 0.714(2) 0.6205(10) 0.024(3) Uani 1 1 d . . . . . C00I C 0.7616(7) 0.725(2) 0.6647(9) 0.018(4) Uani 1 1 d D . . . . O00J O -0.0061(6) 0.5452(18) 0.1545(7) 0.024(3) Uani 1 1 d . . . . . N4 N 0.8743(7) 0.667(2) 0.6646(10) 0.026(4) Uani 1 1 d D . . . . N3 N 0.1593(8) 0.4301(18) 0.3612(11) 0.020(3) Uani 1 1 d . . . . . C00M C 0.8929(7) 0.798(2) 0.7400(10) 0.015(3) Uani 1 1 d D . . . . N1 N 0.6501(8) 0.245(2) 0.6043(10) 0.023(3) Uani 1 1 d . . . . . C00O C 0.4280(8) 0.193(3) 0.4809(12) 0.025(4) Uani 1 1 d . . . . . N6 N 0.9744(7) 0.887(2) 0.7966(9) 0.017(3) Uani 1 1 d . . . . . C00Q C 0.2272(8) 0.722(2) 0.4595(10) 0.018(3) Uani 1 1 d . . . . . O17 O 0.8241(6) 1.1207(19) 0.7879(8) 0.030(3) Uani 1 1 d . . . . . O11 O 0.3303(7) -0.029(2) 0.3722(9) 0.035(4) Uani 1 1 d . . . . . C10 C 0.1641(9) 0.614(2) 0.3724(12) 0.017(3) Uani 1 1 d . . . . . O00U O 0.6692(5) 0.1095(17) 0.5737(7) 0.030(3) Uani 1 1 d . . . . . C00V C 0.5605(7) 0.255(2) 0.5583(10) 0.021(4) Uani 1 1 d D . . . . C00W C 0.8260(6) 0.834(2) 0.7465(9) 0.015(3) Uani 1 1 d D . . . . O15 O -0.0258(6) 0.8333(18) 0.1271(8) 0.034(3) Uani 1 1 d . . . . . O10 O 0.7032(6) 0.3574(19) 0.6728(8) 0.033(3) Uani 1 1 d . . . . . O14 O 1.0245(5) 0.8306(16) 0.7783(7) 0.022(3) Uani 1 1 d . . . . . N10 N 0.4508(6) 0.335(2) 0.5441(9) 0.025(3) Uani 1 1 d . . . . . N9 N 0.5341(7) 0.3796(19) 0.5953(8) 0.025(3) Uani 1 1 d D . . . . N15 N 0.8236(7) 0.969(2) 0.8139(10) 0.023(4) Uani 1 1 d . . . . . O16 O 0.5100(6) 0.0205(18) 0.3531(8) 0.042(4) Uani 1 1 d . . . . . N12 N 0.3095(6) 0.675(2) 0.5685(9) 0.019(3) Uani 1 1 d . . . . . C12 C 0.1019(8) 0.733(2) 0.2921(10) 0.017(3) Uani 1 1 d . . . . . N13 N 0.2073(6) 0.892(2) 0.4373(9) 0.022(3) Uani 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 O001 0.038(5) 0.026(11) 0.045(6) 0.003(5) 0.036(5) 0.006(5) N11 0.019(5) 0.033(13) 0.013(6) 0.008(5) 0.013(5) 0.008(6) O003 0.026(5) 0.021(11) 0.028(5) -0.001(4) 0.013(4) -0.008(5) O004 0.026(5) 0.037(13) 0.031(6) -0.001(5) 0.012(5) 0.007(6) O005 0.045(5) 0.043(13) 0.034(6) -0.016(4) 0.034(5) -0.020(6) N14 0.020(5) 0.013(11) 0.032(6) -0.001(5) 0.015(4) 0.005(5) O007 0.024(4) 0.050(12) 0.026(5) -0.012(5) 0.018(4) -0.005(5) N2 0.025(5) 0.017(12) 0.034(7) 0.006(5) 0.022(5) 0.001(6) O009 0.026(6) 0.021(12) 0.031(7) -0.009(4) 0.016(5) -0.004(5) N00A 0.013(5) 0.036(13) 0.029(6) -0.007(5) 0.011(5) 0.000(6) C9 0.028(6) 0.026(12) 0.016(7) 0.003(5) 0.016(6) -0.002(6) O12 0.030(6) 0.027(10) 0.030(5) 0.004(4) 0.023(5) 0.006(5) O13 0.021(5) 0.021(11) 0.033(6) -0.008(4) 0.012(5) -0.002(5) O00E 0.038(5) 0.043(13) 0.018(5) -0.012(4) 0.017(5) -0.003(6) O00F 0.020(5) 0.048(12) 0.024(5) 0.005(4) 0.012(4) -0.007(5) N8 0.019(6) 0.032(13) 0.018(6) -0.007(5) 0.009(5) 0.003(7) N7 0.020(6) 0.031(12) 0.023(7) -0.003(5) 0.015(5) -0.009(6) C00I 0.011(5) 0.021(14) 0.017(7) 0.003(5) 0.007(5) -0.003(5) O00J 0.023(6) 0.030(11) 0.019(5) -0.001(4) 0.012(5) 0.001(5) N4 0.022(5) 0.020(14) 0.034(8) -0.010(5) 0.017(5) -0.012(6) N3 0.014(4) 0.029(9) 0.016(5) -0.001(5) 0.008(4) -0.001(7) C00M 0.012(5) 0.007(13) 0.025(8) 0.007(5) 0.011(5) 0.008(5) N1 0.020(5) 0.027(12) 0.022(6) 0.011(5) 0.013(5) 0.007(6) C00O 0.025(6) 0.041(14) 0.012(7) 0.002(5) 0.014(6) 0.002(6) N6 0.009(4) 0.025(12) 0.009(6) -0.001(4) 0.002(4) 0.000(5) C00Q 0.020(6) 0.025(11) 0.015(6) 0.001(5) 0.014(4) 0.000(6) O17 0.028(5) 0.032(12) 0.028(6) -0.008(5) 0.017(4) 0.002(7) O11 0.034(6) 0.034(13) 0.034(6) -0.012(5) 0.020(5) -0.002(5) C10 0.018(5) 0.019(9) 0.015(6) 0.003(5) 0.011(4) 0.004(7) O00U 0.022(4) 0.047(12) 0.024(5) -0.003(4) 0.017(4) 0.003(5) C00V 0.022(6) 0.025(13) 0.022(7) 0.000(5) 0.017(6) 0.001(6) C00W 0.004(5) 0.027(12) 0.004(6) 0.004(4) -0.002(5) 0.006(5) O15 0.026(5) 0.035(12) 0.038(7) 0.018(5) 0.017(5) 0.006(5) O10 0.026(5) 0.030(13) 0.033(6) 0.001(4) 0.014(5) 0.001(5) O14 0.015(4) 0.027(11) 0.029(6) 0.003(4) 0.016(4) 0.000(4) N10 0.019(5) 0.041(13) 0.013(6) 0.002(5) 0.009(5) 0.007(5) N9 0.023(5) 0.031(13) 0.024(7) 0.008(5) 0.015(5) 0.010(6) N15 0.014(6) 0.029(13) 0.031(7) -0.007(5) 0.016(6) -0.009(6) O16 0.033(6) 0.074(14) 0.034(7) -0.008(5) 0.028(5) -0.010(5) N12 0.017(5) 0.022(11) 0.026(6) 0.000(5) 0.017(5) -0.001(6) C12 0.023(6) 0.019(11) 0.013(6) 0.002(4) 0.013(5) 0.006(6) N13 0.023(5) 0.017(10) 0.026(6) 0.002(4) 0.015(5) 0.009(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' 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 _geom_angle_publ_flag O00J N11 O15 128.0(14) . . ? O00J N11 C12 117.8(12) . . ? O15 N11 C12 114.2(15) . . ? C12 N14 N13 108.8(13) . . ? O001 N2 C00O 117.2(15) . . ? O001 N2 O11 125.9(14) . . ? O11 N2 C00O 116.8(13) . . ? N4 N00A C00I 113.5(11) . . ? C00O C9 N8 127.8(14) . . ? C00V C9 N8 129.4(10) . . ? C00V C9 C00O 102.8(13) . . ? O004 N8 C9 117.6(13) . . ? O16 N8 O004 126.2(15) . . ? O16 N8 C9 116.2(16) . . ? O003 N7 C00I 116.3(11) . . ? O007 N7 O003 127.3(11) . . ? O007 N7 C00I 116.4(12) . . ? N00A C00I N7 121.5(12) . . ? N00A C00I C00W 108.2(10) . . ? C00W C00I N7 130.0(12) . . ? N00A N4 C00M 101.6(10) . . ? O00E N3 C10 118.9(11) . . ? O00F N3 O00E 121.6(14) . . ? O00F N3 C10 119.3(11) . . ? N4 C00M N6 117.9(9) . . ? N4 C00M C00W 113.8(11) . . ? C00W C00M N6 128.2(12) . . ? O00U N1 C00V 114.5(13) . . ? O10 N1 O00U 124.4(11) . . ? O10 N1 C00V 121.0(13) . . ? C9 C00O N2 129.1(15) . . ? N10 C00O N2 121.7(12) . . ? N10 C00O C9 109.0(13) . . ? O009 N6 C00M 117.7(11) . . ? O14 N6 O009 125.0(13) . . ? O14 N6 C00M 116.7(12) . . ? C10 C00Q N12 129.1(16) . . ? N13 C00Q C10 113.2(13) . . ? N13 C00Q N12 117.7(13) . . ? C00Q C10 N3 131.3(13) . . ? C00Q C10 C12 102.3(14) . . ? C12 C10 N3 126.3(13) . . ? C9 C00V N1 126.0(14) . . ? N9 C00V C9 113.2(10) . . ? N9 C00V N1 120.3(12) . . ? C00I C00W C00M 102.8(12) . . ? C00I C00W N15 129.3(10) . . ? C00M C00W N15 127.5(12) . . ? C00O N10 N9 111.9(11) . . ? C00V N9 N10 103.0(11) . . ? O005 N15 C00W 115.8(17) . . ? O17 N15 O005 127.1(16) . . ? O17 N15 C00W 117.1(12) . . ? O12 N12 O13 127.5(14) . . ? O12 N12 C00Q 114.8(12) . . ? O13 N12 C00Q 117.7(17) . . ? N14 C12 N11 120.8(13) . . ? N14 C12 C10 110.5(12) . . ? C10 C12 N11 128.7(15) . . ? C00Q N13 N14 105.2(13) . . ? 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 O001 N2 1.211(16) . ? N11 O00J 1.215(17) . ? N11 O15 1.241(17) . ? N11 C12 1.461(17) . ? O003 N7 1.227(16) . ? O004 N8 1.254(19) . ? O005 N15 1.220(15) . ? N14 C12 1.325(19) . ? N14 N13 1.363(13) . ? O007 N7 1.195(15) . ? N2 C00O 1.430(19) . ? N2 O11 1.26(2) . ? O009 N6 1.236(18) . ? N00A C00I 1.332(15) . ? N00A N4 1.327(15) . ? C9 N8 1.43(2) . ? C9 C00O 1.364(17) . ? C9 C00V 1.36(2) . ? O12 N12 1.208(19) . ? O13 N12 1.221(17) . ? O00E N3 1.242(15) . ? O00F N3 1.221(17) . ? N8 O16 1.242(15) . ? N7 C00I 1.423(15) . ? C00I C00W 1.351(18) . ? N4 C00M 1.349(18) . ? N3 C10 1.396(17) . ? C00M N6 1.427(17) . ? C00M C00W 1.377(15) . ? N1 O00U 1.256(17) . ? N1 C00V 1.427(15) . ? N1 O10 1.233(19) . ? C00O N10 1.30(2) . ? N6 O14 1.226(14) . ? C00Q C10 1.37(2) . ? C00Q N12 1.441(16) . ? C00Q N13 1.33(2) . ? O17 N15 1.209(19) . ? C10 C12 1.38(2) . ? C00V N9 1.329(17) . ? C00W N15 1.43(2) . ? N10 N9 1.342(15) . ? 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 O001 N2 C00O C9 -178.9(15) . . . . ? O001 N2 C00O N10 7(3) . . . . ? O003 N7 C00I N00A -2(2) . . . . ? O003 N7 C00I C00W 171.5(15) . . . . ? O007 N7 C00I N00A 180.0(13) . . . . ? O007 N7 C00I C00W -7(2) . . . . ? N2 C00O N10 N9 175.6(12) . . . . ? N00A C00I C00W C00M 2.0(15) . . . . ? N00A C00I C00W N15 175.1(16) . . . . ? N00A N4 C00M N6 -172.4(12) . . . . ? N00A N4 C00M C00W 4(2) . . . . ? C9 C00O N10 N9 0(2) . . . . ? C9 C00V N9 N10 -0.4(18) . . . . ? O00E N3 C10 C00Q -120.9(14) . . . . ? O00E N3 C10 C12 59.1(17) . . . . ? O00F N3 C10 C00Q 53.3(18) . . . . ? O00F N3 C10 C12 -126.7(14) . . . . ? N8 C9 C00O N2 7(3) . . . . ? N8 C9 C00O N10 -178.0(17) . . . . ? N8 C9 C00V N1 -10(3) . . . . ? N8 C9 C00V N9 178.1(15) . . . . ? N7 C00I C00W C00M -172.1(14) . . . . ? N7 C00I C00W N15 1(3) . . . . ? C00I N00A N4 C00M -2.5(17) . . . . ? C00I C00W N15 O005 73.3(19) . . . . ? C00I C00W N15 O17 -106.4(18) . . . . ? O00J N11 C12 N14 -175.9(8) . . . . ? O00J N11 C12 C10 0.8(16) . . . . ? N4 N00A C00I N7 175.1(14) . . . . ? N4 N00A C00I C00W 0.3(16) . . . . ? N4 C00M N6 O009 167.4(17) . . . . ? N4 C00M N6 O14 -5(2) . . . . ? N4 C00M C00W C00I -3.8(19) . . . . ? N4 C00M C00W N15 -177.1(16) . . . . ? N3 C10 C12 N11 3.5(19) . . . . ? N3 C10 C12 N14 -179.6(9) . . . . ? C00M C00W N15 O005 -115.2(16) . . . . ? C00M C00W N15 O17 65(2) . . . . ? N1 C00V N9 N10 -173.1(12) . . . . ? C00O C9 N8 O004 -66(2) . . . . ? C00O C9 N8 O16 112.6(17) . . . . ? C00O C9 C00V N1 172.6(13) . . . . ? C00O C9 C00V N9 0.5(19) . . . . ? C00O N10 N9 C00V 0.2(19) . . . . ? N6 C00M C00W C00I 172.1(14) . . . . ? N6 C00M C00W N15 -1(3) . . . . ? C00Q C10 C12 N11 -176.5(9) . . . . ? C00Q C10 C12 N14 0.4(13) . . . . ? O11 N2 C00O C9 -1(3) . . . . ? O11 N2 C00O N10 -175.2(19) . . . . ? C10 C00Q N12 O12 10.0(16) . . . . ? C10 C00Q N12 O13 -172.0(12) . . . . ? C10 C00Q N13 N14 -0.4(11) . . . . ? O00U N1 C00V C9 0(2) . . . . ? O00U N1 C00V N9 171.7(14) . . . . ? C00V C9 N8 O004 117.0(18) . . . . ? C00V C9 N8 O16 -64(2) . . . . ? C00V C9 C00O N2 -175.4(16) . . . . ? C00V C9 C00O N10 -0.3(19) . . . . ? C00W C00M N6 O009 -8(2) . . . . ? C00W C00M N6 O14 179.6(14) . . . . ? O15 N11 C12 N14 3.7(13) . . . . ? O15 N11 C12 C10 -179.6(10) . . . . ? O10 N1 C00V C9 -176.6(16) . . . . ? O10 N1 C00V N9 -5(2) . . . . ? N12 C00Q C10 N3 0(2) . . . . ? N12 C00Q C10 C12 -179.9(9) . . . . ? N12 C00Q N13 N14 179.5(7) . . . . ? C12 N14 N13 C00Q 0.7(10) . . . . ? N13 N14 C12 N11 176.5(8) . . . . ? N13 N14 C12 C10 -0.7(12) . . . . ? N13 C00Q C10 N3 180.0(11) . . . . ? N13 C00Q C10 C12 0.0(13) . . . . ? N13 C00Q N12 O12 -169.9(9) . . . . ? N13 C00Q N12 O13 8.1(14) . . . . ?