#------------------------------------------------------------------------------ #$Date: 2020-05-07 00:20:09 +0300 (Thu, 07 May 2020) $ #$Revision: 251830 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240473.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_7240473 loop_ _publ_author_name 'Campillo-Alvarado, Gonzalo' 'Keene, Elizabeth' 'Swenson, Dale C.' 'MacGillivray, Len R.' _publ_section_title ; Repurposing of the anti-HIV drug Emtricitabine as a hydrogen-bonded cleft for bipyridines via cocrystallization ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/D0CE00474J _journal_year 2020 _chemical_formula_moiety 'C8 H9 F N3 O3 S, C8 H10 F N3 O3 S, C10 H8 N4' _chemical_formula_sum 'C26 H27 F2 N10 O6 S2' _chemical_formula_weight 677.69 _chemical_name_systematic '[4-amino-5-fluoro-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1H)-one]-[4-azopyridine]'' _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2019-10-06 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2020-02-03 deposited with the CCDC. 2020-05-06 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 100.538(5) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 7.5024(8) _cell_length_b 11.2194(11) _cell_length_c 18.2134(18) _cell_measurement_reflns_used 9829 _cell_measurement_temperature 296.15 _cell_measurement_theta_max 27.265 _cell_measurement_theta_min 2.2745 _cell_volume 1507.2(3) _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 296.15 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'Bruker D-8 Venture Duo-Photon 3' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0428 _diffrn_reflns_av_unetI/netI 0.0350 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.995 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 32670 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.981 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.893 _diffrn_reflns_theta_min 2.275 _exptl_absorpt_coefficient_mu 0.249 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.7261 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0713 before and 0.0535 after correction. The Ratio of minimum to maximum transmission is 0.9738. The \l/2 correction factor is Not present.' _exptl_crystal_colour orange _exptl_crystal_colour_primary orange _exptl_crystal_density_diffrn 1.493 _exptl_crystal_description plate _exptl_crystal_F_000 702 _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.095 _exptl_crystal_size_min 0.02 _refine_diff_density_max 0.479 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.044 _refine_ls_abs_structure_details ; Flack x determined using 2297 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.04(2) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 424 _refine_ls_number_reflns 7064 _refine_ls_number_restraints 6 _refine_ls_restrained_S_all 1.073 _refine_ls_R_factor_all 0.0591 _refine_ls_R_factor_gt 0.0487 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0514P)^2^+0.5135P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1106 _refine_ls_wR_factor_ref 0.1157 _reflns_Friedel_coverage 0.877 _reflns_Friedel_fraction_full 0.995 _reflns_Friedel_fraction_max 0.965 _reflns_number_gt 6093 _reflns_number_total 7064 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ce00474j2.cif _cod_data_source_block FTC-apy _cod_database_code 7240473 _shelx_shelxl_version_number 2016/6 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_max 0.995 _shelx_estimated_absorpt_t_min 0.968 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H,H) groups At 1.5 times of: All O(H) groups 2. Restrained distances N9-C19 \\sim N9B-C19 with sigma of 0.02 N9-N10 \\sim N9B-N10B with sigma of 0.02 C24-N10 \\sim C24-N10B with sigma of 0.02 N9-C24 \\sim N9B-C24 with sigma of 0.04 C19-N10 \\sim C19-N10B with sigma of 0.04 3. Uiso/Uaniso restraints and constraints Uanis(N10) = Uanis(N10B) Uanis(N9B) = Uanis(N9) 4. Others Sof(N10B)=Sof(N9B)=1-FVAR(1) Sof(N9)=Sof(N10)=FVAR(1) 5.a Ternary CH refined with riding coordinates: C12(H12), C10(H10), C4(H4), C2(H2) 5.b Secondary CH2 refined with riding coordinates: C11(H11A,H11B), C3(H3C,H3D), C1(H1A,H1B) 5.c Aromatic/amide H refined with riding coordinates: C8(H8), C14(H14), C22(H22), C9(H9), C17(H17), C23(H23), C26(H26), C18(H18), C21(H21), C20(H20), C25(H25) 5.d X=CH2 refined with riding coordinates: N3(H3A,H3B), N6(H6A,H6B) 5.e Idealised tetrahedral OH refined as rotating group: O4(H4A), O1(H1) ; _shelx_res_file ; TITL mcg19124_a.res in P2(1) mcg19124.res created by SHELXL-2016/6 at 01:05:51 on 06-Oct-2019 REM Old TITL Mcg19_124 in P2(1) sample #19188 EMT-Azobpe REM SHELXT solution in P2(1) REM R1 0.140, Rweak 0.053, Alpha 0.002, Orientation as input REM Flack x = 0.069 ( 0.023 ) from Parsons' quotients REM Formula found by SHELXT: C31 F4 N6 O3 S2 CELL 0.71073 7.5024 11.2194 18.2134 90 100.538 90 ZERR 2 0.0008 0.0011 0.0018 0 0.005 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H F N O S UNIT 52 54 4 20 12 4 SADI N9 C19 N9B C19 SADI N9 N10 N9B N10B SADI C24 N10 C24 N10B SADI 0.04 N9 C24 N9B C24 SADI 0.04 C19 N10 C19 N10B EADP N10 N10B EADP N9B N9 L.S. 10 PLAN 20 SIZE 0.02 0.095 0.13 TEMP 23 BOND $H CONF HTAB list 4 fmap 2 acta REM REM REM WGHT 0.051400 0.513500 FVAR 1.04419 0.90034 S2 6 0.215234 0.657853 1.168769 11.00000 0.05375 0.04763 = 0.03849 -0.01418 0.01067 -0.00175 S1 6 -0.038784 0.446520 0.307889 11.00000 0.06215 0.05899 = 0.02618 -0.00313 -0.00163 0.01477 F1 3 0.262869 0.183455 0.633416 11.00000 0.07795 0.03510 = 0.04528 0.00656 0.00828 0.00870 F2 3 0.176310 0.817228 0.886335 11.00000 0.10915 0.03085 = 0.04249 0.00275 0.02680 -0.00636 O5 5 0.300698 0.481099 1.091052 11.00000 0.04831 0.04694 = 0.02792 -0.00321 0.00515 0.01504 O3 5 -0.008029 0.617328 0.569878 11.00000 0.09630 0.03569 = 0.03681 -0.00068 0.01040 0.01920 O6 5 0.074682 0.358965 0.937504 11.00000 0.10166 0.03140 = 0.03925 -0.00141 0.01004 -0.00617 O2 5 0.217829 0.477344 0.425425 11.00000 0.04837 0.06580 = 0.02854 -0.00758 0.00946 -0.01206 N1 4 0.080944 0.439902 0.527972 11.00000 0.04558 0.03184 = 0.02573 -0.00203 0.00483 0.00255 N4 4 0.110012 0.547621 0.983013 11.00000 0.04234 0.03054 = 0.02371 -0.00019 0.00385 -0.00317 N5 4 0.089302 0.505926 0.853460 11.00000 0.05544 0.03295 = 0.02629 -0.00135 0.00271 0.00124 O4 5 0.617479 0.634104 1.156770 11.00000 0.04721 0.12054 = 0.05498 -0.02783 0.01557 -0.02036 AFIX 147 H4A 2 0.625193 0.618401 1.113492 11.00000 -1.50000 AFIX 0 O1 5 0.481835 0.333402 0.364334 11.00000 0.05233 0.09746 = 0.06128 -0.01811 0.01276 0.00458 AFIX 147 H1 2 0.504927 0.350204 0.408880 11.00000 -1.50000 AFIX 0 N2 4 0.080447 0.474586 0.656621 11.00000 0.05412 0.04140 = 0.02523 -0.00381 0.00645 0.00208 C8 1 0.152546 0.329007 0.544494 11.00000 0.04537 0.03153 = 0.03083 -0.00520 0.00950 -0.00191 AFIX 43 H8 2 0.176807 0.279713 0.506464 11.00000 -1.20000 AFIX 0 N8 4 0.610978 0.589445 0.999807 11.00000 0.04832 0.07452 = 0.04531 -0.00905 0.01044 0.00020 N7 4 0.608476 0.385750 0.520292 11.00000 0.05647 0.08168 = 0.04498 -0.00486 0.00564 -0.00679 N3 4 0.169838 0.328770 0.743273 11.00000 0.08459 0.04750 = 0.02746 0.00385 0.01063 0.00575 AFIX 93 H3A 2 0.143121 0.374761 0.777452 11.00000 -1.20000 H3B 2 0.212139 0.258580 0.754624 11.00000 -1.20000 AFIX 0 C12 1 0.115171 0.501858 1.058525 11.00000 0.04335 0.03266 = 0.02632 0.00092 0.00876 -0.00486 AFIX 13 H12 2 0.050971 0.425407 1.054851 11.00000 -1.20000 AFIX 0 C10 1 0.343761 0.521830 1.166040 11.00000 0.04998 0.04831 = 0.02255 0.00348 0.00778 0.00605 AFIX 13 H10 2 0.302211 0.462636 1.198720 11.00000 -1.20000 AFIX 0 C7 1 0.187573 0.291533 0.615044 11.00000 0.04719 0.02804 = 0.03494 -0.00030 0.00763 -0.00163 C4 1 0.049232 0.482230 0.451194 11.00000 0.04988 0.03374 = 0.02766 -0.00211 0.00621 0.00357 AFIX 13 H4 2 0.009159 0.565428 0.450458 11.00000 -1.20000 AFIX 0 C5 1 0.048664 0.516735 0.585500 11.00000 0.04862 0.03327 = 0.02822 -0.00601 0.00718 -0.00114 C14 1 0.143209 0.665230 0.970593 11.00000 0.04491 0.03206 = 0.03188 -0.00574 0.00778 -0.00255 AFIX 43 H14 2 0.164694 0.718982 1.010096 11.00000 -1.20000 AFIX 0 C11 1 0.029154 0.584605 1.109376 11.00000 0.03968 0.04443 = 0.03618 -0.00112 0.01389 -0.00054 AFIX 23 H11A 2 -0.041926 0.539067 1.138962 11.00000 -1.20000 H11B 2 -0.049235 0.642561 1.079932 11.00000 -1.20000 AFIX 0 N6 4 0.107654 0.657665 0.771144 11.00000 0.10039 0.04005 = 0.02795 0.00696 0.01100 0.00396 AFIX 93 H6A 2 0.089535 0.607797 0.734678 11.00000 -1.20000 H6B 2 0.122717 0.732055 0.762660 11.00000 -1.20000 AFIX 0 C13 1 0.089727 0.463985 0.924200 11.00000 0.04496 0.03416 = 0.02839 -0.00445 0.00382 -0.00238 C3 1 -0.088408 0.411707 0.398437 11.00000 0.04372 0.05400 = 0.03137 0.00060 0.00283 0.00055 AFIX 23 H3C 2 -0.210682 0.435806 0.402034 11.00000 -1.20000 H3D 2 -0.075078 0.327022 0.408713 11.00000 -1.20000 AFIX 0 C2 1 0.202283 0.446649 0.348403 11.00000 0.05911 0.04708 = 0.02490 0.00124 0.01160 -0.00645 AFIX 13 H2 2 0.262742 0.508078 0.323568 11.00000 -1.20000 AFIX 0 C15 1 0.144227 0.701279 0.901256 11.00000 0.05080 0.02848 = 0.03360 0.00088 0.01174 0.00190 PART 1 N9 4 0.619896 0.437541 0.750184 21.00000 0.06862 0.04640 = 0.04695 0.00108 0.01152 -0.00009 PART 0 C22 1 0.578804 0.481406 0.970165 11.00000 0.05987 0.06670 = 0.05413 0.00585 0.01718 -0.00110 AFIX 43 H22 2 0.555904 0.419825 1.001338 11.00000 -1.20000 AFIX 0 C6 1 0.145887 0.365963 0.673294 11.00000 0.04173 0.03636 = 0.02790 0.00092 0.00414 -0.00624 C1 1 0.293361 0.327489 0.340698 11.00000 0.05047 0.05663 = 0.04377 -0.00167 0.01349 0.00181 AFIX 23 H1A 2 0.243912 0.268151 0.370128 11.00000 -1.20000 H1B 2 0.266758 0.302429 0.288874 11.00000 -1.20000 AFIX 0 C9 1 0.543453 0.536682 1.188568 11.00000 0.05028 0.10290 = 0.03941 -0.00075 -0.00196 0.00925 AFIX 43 H9 2 0.614151 0.484739 1.221530 11.00000 -1.20000 AFIX 0 C17 1 0.661962 0.303632 0.571446 11.00000 0.05925 0.06821 = 0.05448 -0.01427 0.00865 0.00313 AFIX 43 H17 2 0.696263 0.229692 0.555597 11.00000 -1.20000 AFIX 0 C23 1 0.577310 0.454942 0.895609 11.00000 0.06097 0.05811 = 0.05841 -0.01288 0.01168 -0.00074 AFIX 43 H23 2 0.554605 0.378089 0.877119 11.00000 -1.20000 AFIX 0 C16 1 0.112392 0.619663 0.840804 11.00000 0.04300 0.03981 = 0.02995 -0.00065 0.00589 0.00692 C26 1 0.642601 0.675382 0.954404 11.00000 0.05892 0.05585 = 0.06276 -0.01117 0.01163 -0.00869 AFIX 43 H26 2 0.666435 0.751236 0.974388 11.00000 -1.20000 AFIX 0 C18 1 0.670064 0.320615 0.646476 11.00000 0.05961 0.06952 = 0.05050 0.00030 0.00691 0.00240 AFIX 43 H18 2 0.709563 0.260126 0.680484 11.00000 -1.20000 AFIX 0 C19 1 0.618196 0.429557 0.670159 11.00000 0.04635 0.06533 = 0.04144 -0.00225 0.00241 -0.00684 C24 1 0.611190 0.548160 0.849686 11.00000 0.04524 0.06921 = 0.04112 -0.00118 0.00611 0.00367 C21 1 0.561519 0.492735 0.544049 11.00000 0.06180 0.07061 = 0.05201 0.00798 -0.00332 -0.01223 AFIX 43 H21 2 0.526554 0.552272 0.508830 11.00000 -1.20000 AFIX 0 C20 1 0.562790 0.518360 0.618380 11.00000 0.05504 0.05889 = 0.06506 -0.00980 0.00616 -0.00964 AFIX 43 H20 2 0.527568 0.592812 0.633060 11.00000 -1.20000 AFIX 0 PART 1 N10 4 0.614256 0.539174 0.770643 21.00000 0.07816 0.05187 = 0.04584 0.00084 0.00956 -0.00564 PART 0 C25 1 0.642635 0.660255 0.879962 11.00000 0.07180 0.06218 = 0.05412 0.00432 0.01363 -0.00806 AFIX 43 H25 2 0.663495 0.724440 0.850346 11.00000 -1.20000 AFIX 0 PART 2 N10B 4 0.593828 0.465437 0.785709 -21.00000 0.07816 0.05187 = 0.04584 0.00084 0.00956 -0.00564 N9B 4 0.618245 0.514651 0.730095 -21.00000 0.06862 0.04640 = 0.04695 0.00108 0.01152 -0.00009 HKLF 4 REM mcg19124_a.res in P2(1) REM R1 = 0.0487 for 6093 Fo > 4sig(Fo) and 0.0591 for all 7064 data REM 424 parameters refined using 6 restraints END WGHT 0.0514 0.5134 REM Instructions for potential hydrogen bonds HTAB O4 N8 HTAB O1 N7 EQIV $1 -x, y-1/2, -z+1 HTAB C8 O3_$1 HTAB N3 N5 EQIV $2 -x+1, y-1/2, -z+2 HTAB N3 O4_$2 EQIV $3 -x, y-1/2, -z+2 HTAB C12 F2_$3 HTAB C14 S2 EQIV $4 -x, y+1/2, -z+2 HTAB C11 O6_$4 HTAB N6 N2 EQIV $5 -x, y+1/2, -z+1 HTAB N6 S1_$5 EQIV $6 x-1, y, z HTAB C3 O1_$6 HTAB C3 O3_$1 EQIV $7 x+1, y, z+1 HTAB C9 S1_$7 EQIV $8 -x+1, y+1/2, -z+2 HTAB C26 O6_$8 HTAB C18 S2_$2 REM Highest difference peak 0.479, deepest hole -0.222, 1-sigma level 0.044 Q1 1 0.6262 0.7534 0.8324 11.00000 0.05 0.48 Q2 1 0.5943 0.4487 1.1760 11.00000 0.05 0.28 Q3 1 0.7502 0.2478 0.6708 11.00000 0.05 0.26 Q4 1 0.5034 0.3039 0.8993 11.00000 0.05 0.25 Q5 1 0.5607 0.5636 1.2404 11.00000 0.05 0.25 Q6 1 0.4446 0.6446 0.6152 11.00000 0.05 0.25 Q7 1 0.4482 0.4263 0.3600 11.00000 0.05 0.23 Q8 1 0.5890 0.8362 0.8402 11.00000 0.05 0.19 Q9 1 0.5386 0.4977 0.3632 11.00000 0.05 0.17 Q10 1 0.5187 0.5002 0.7362 11.00000 0.05 0.17 Q11 1 0.6023 0.4932 0.8588 11.00000 0.05 0.16 Q12 1 -0.0910 0.3828 0.3331 11.00000 0.05 0.16 Q13 1 0.2110 0.4550 0.7645 11.00000 0.05 0.16 Q14 1 -0.1249 0.4106 0.3308 11.00000 0.05 0.16 Q15 1 0.0559 0.5205 0.9483 11.00000 0.05 0.16 Q16 1 0.1823 0.5000 0.8518 11.00000 0.05 0.15 Q17 1 0.0927 0.4251 0.3295 11.00000 0.05 0.15 Q18 1 0.5859 0.5623 0.5212 11.00000 0.05 0.15 Q19 1 0.5993 0.4554 0.4901 11.00000 0.05 0.15 Q20 1 0.5015 0.5102 0.7712 11.00000 0.05 0.15 ; _shelx_res_checksum 97927 _olex2_date_sample_data_collection 2019-09-17 _olex2_date_sample_submission 2019-09-03 _olex2_submission_original_sample_id FTC-apy _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, 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 _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S2 S 0.21523(15) 0.65785(9) 1.16877(6) 0.0463(3) Uani 1 1 d . . . . . S1 S -0.03878(16) 0.44652(11) 0.30789(5) 0.0503(3) Uani 1 1 d . . . . . F1 F 0.2629(4) 0.1835(2) 0.63342(13) 0.0532(6) Uani 1 1 d . . . . . F2 F 0.1763(4) 0.8172(2) 0.88634(14) 0.0592(7) Uani 1 1 d . . . . . O5 O 0.3007(4) 0.4811(2) 1.09105(13) 0.0413(6) Uani 1 1 d . . . . . O3 O -0.0080(5) 0.6173(3) 0.56988(16) 0.0565(9) Uani 1 1 d . . . . . O6 O 0.0747(5) 0.3590(3) 0.93750(17) 0.0578(9) Uani 1 1 d . . . . . O2 O 0.2178(4) 0.4773(3) 0.42543(14) 0.0473(7) Uani 1 1 d . . . . . N1 N 0.0809(4) 0.4399(3) 0.52797(15) 0.0346(6) Uani 1 1 d . . . . . N4 N 0.1100(4) 0.5476(3) 0.98301(15) 0.0325(6) Uani 1 1 d . . . . . N5 N 0.0893(5) 0.5059(3) 0.85346(17) 0.0388(7) Uani 1 1 d . . . . . O4 O 0.6175(5) 0.6341(4) 1.1568(2) 0.0735(12) Uani 1 1 d . . . . . H4A H 0.625193 0.618401 1.113492 0.110 Uiso 1 1 calc GR . . . . O1 O 0.4818(5) 0.3334(4) 0.3643(2) 0.0701(10) Uani 1 1 d . . . . . H1 H 0.504927 0.350204 0.408880 0.105 Uiso 1 1 calc GR . . . . N2 N 0.0804(5) 0.4746(3) 0.65662(16) 0.0404(7) Uani 1 1 d . . . . . C8 C 0.1525(5) 0.3290(3) 0.5445(2) 0.0356(8) Uani 1 1 d . . . . . H8 H 0.176807 0.279713 0.506464 0.043 Uiso 1 1 calc R . . . . N8 N 0.6110(5) 0.5894(4) 0.9998(2) 0.0558(10) Uani 1 1 d . . . . . N7 N 0.6085(6) 0.3857(4) 0.5203(2) 0.0615(11) Uani 1 1 d . . . . . N3 N 0.1698(6) 0.3288(3) 0.74327(18) 0.0531(9) Uani 1 1 d . . . . . H3A H 0.143121 0.374761 0.777452 0.064 Uiso 1 1 calc R . . . . H3B H 0.212139 0.258580 0.754624 0.064 Uiso 1 1 calc R . . . . C12 C 0.1152(5) 0.5019(3) 1.05853(19) 0.0338(8) Uani 1 1 d . . . . . H12 H 0.050971 0.425407 1.054851 0.041 Uiso 1 1 calc R . . . . C10 C 0.3438(6) 0.5218(4) 1.16604(19) 0.0401(9) Uani 1 1 d . . . . . H10 H 0.302211 0.462636 1.198720 0.048 Uiso 1 1 calc R . . . . C7 C 0.1876(5) 0.2915(3) 0.6150(2) 0.0367(8) Uani 1 1 d . . . . . C4 C 0.0492(5) 0.4822(3) 0.45119(19) 0.0372(8) Uani 1 1 d . . . . . H4 H 0.009159 0.565428 0.450458 0.045 Uiso 1 1 calc R . . . . C5 C 0.0487(5) 0.5167(3) 0.58550(19) 0.0367(8) Uani 1 1 d . . . . . C14 C 0.1432(5) 0.6652(4) 0.9706(2) 0.0362(7) Uani 1 1 d . . . . . H14 H 0.164694 0.718982 1.010096 0.043 Uiso 1 1 calc R . . . . C11 C 0.0292(5) 0.5846(4) 1.1094(2) 0.0392(8) Uani 1 1 d . . . . . H11A H -0.041926 0.539067 1.138962 0.047 Uiso 1 1 calc R . . . . H11B H -0.049235 0.642561 1.079932 0.047 Uiso 1 1 calc R . . . . N6 N 0.1077(6) 0.6577(3) 0.77114(18) 0.0562(10) Uani 1 1 d . . . . . H6A H 0.089535 0.607797 0.734678 0.067 Uiso 1 1 calc R . . . . H6B H 0.122717 0.732055 0.762660 0.067 Uiso 1 1 calc R . . . . C13 C 0.0897(5) 0.4640(3) 0.92420(19) 0.0362(8) Uani 1 1 d . . . . . C3 C -0.0884(6) 0.4117(4) 0.3984(2) 0.0435(9) Uani 1 1 d . . . . . H3C H -0.210682 0.435806 0.402034 0.052 Uiso 1 1 calc R . . . . H3D H -0.075078 0.327022 0.408713 0.052 Uiso 1 1 calc R . . . . C2 C 0.2023(6) 0.4466(4) 0.34840(19) 0.0432(9) Uani 1 1 d . . . . . H2 H 0.262742 0.508078 0.323568 0.052 Uiso 1 1 calc R . . . . C15 C 0.1442(6) 0.7013(3) 0.9013(2) 0.0371(8) Uani 1 1 d . . . . . N9 N 0.6199(6) 0.4375(4) 0.7502(2) 0.0539(12) Uani 0.900(8) 1 d D . P A 1 C22 C 0.5788(7) 0.4814(5) 0.9702(3) 0.0594(12) Uani 1 1 d . . . . . H22 H 0.555904 0.419825 1.001338 0.071 Uiso 1 1 calc R . . . . C6 C 0.1459(5) 0.3660(3) 0.6733(2) 0.0356(8) Uani 1 1 d . . . . . C1 C 0.2934(6) 0.3275(4) 0.3407(2) 0.0497(10) Uani 1 1 d . . . . . H1A H 0.243912 0.268151 0.370128 0.060 Uiso 1 1 calc R . . . . H1B H 0.266758 0.302429 0.288874 0.060 Uiso 1 1 calc R . . . . C9 C 0.5435(7) 0.5367(6) 1.1886(3) 0.0655(14) Uani 1 1 d . . . . . H9 H 0.614151 0.484739 1.221530 0.079 Uiso 1 1 calc R . . . . C17 C 0.6620(7) 0.3036(5) 0.5714(3) 0.0609(12) Uani 1 1 d . . . . . H17 H 0.696263 0.229692 0.555597 0.073 Uiso 1 1 calc R . . . . C23 C 0.5773(7) 0.4549(5) 0.8956(3) 0.0591(11) Uani 1 1 d . . . . . H23 H 0.554605 0.378089 0.877119 0.071 Uiso 1 1 calc R . . . . C16 C 0.1124(5) 0.6197(4) 0.8408(2) 0.0377(8) Uani 1 1 d . . . . . C26 C 0.6426(7) 0.6754(5) 0.9544(3) 0.0591(12) Uani 1 1 d . . . . . H26 H 0.666435 0.751236 0.974388 0.071 Uiso 1 1 calc R . . . . C18 C 0.6701(7) 0.3206(5) 0.6465(3) 0.0603(12) Uani 1 1 d . . . . . H18 H 0.709563 0.260126 0.680484 0.072 Uiso 1 1 calc R . . . . C19 C 0.6182(6) 0.4296(5) 0.6702(2) 0.0518(11) Uani 1 1 d D . . . . C24 C 0.6112(6) 0.5482(5) 0.8497(2) 0.0521(11) Uani 1 1 d D . . . . C21 C 0.5615(7) 0.4927(5) 0.5440(3) 0.0632(13) Uani 1 1 d . . . . . H21 H 0.526554 0.552272 0.508830 0.076 Uiso 1 1 calc R . . . . C20 C 0.5628(7) 0.5184(5) 0.6184(3) 0.0603(12) Uani 1 1 d . . . . . H20 H 0.527568 0.592812 0.633060 0.072 Uiso 1 1 calc R . . . . N10 N 0.6143(7) 0.5392(4) 0.7706(3) 0.0588(13) Uani 0.900(8) 1 d D . P A 1 C25 C 0.6426(7) 0.6603(5) 0.8800(3) 0.0624(12) Uani 1 1 d . . . . . H25 H 0.663495 0.724440 0.850346 0.075 Uiso 1 1 calc R . . . . N10B N 0.594(7) 0.465(3) 0.7857(15) 0.0588(13) Uani 0.100(8) 1 d D . P A 2 N9B N 0.618(6) 0.515(3) 0.7301(16) 0.0539(12) Uani 0.100(8) 1 d D . P A 2 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 S2 0.0538(6) 0.0476(6) 0.0385(5) -0.0142(4) 0.0107(4) -0.0017(5) S1 0.0621(6) 0.0590(7) 0.0262(4) -0.0031(4) -0.0016(4) 0.0148(6) F1 0.0779(17) 0.0351(13) 0.0453(13) 0.0066(10) 0.0083(12) 0.0087(11) F2 0.109(2) 0.0309(12) 0.0425(13) 0.0027(10) 0.0268(14) -0.0064(13) O5 0.0483(15) 0.0469(16) 0.0279(12) -0.0032(11) 0.0052(11) 0.0150(12) O3 0.096(3) 0.0357(15) 0.0368(15) -0.0007(12) 0.0104(15) 0.0192(16) O6 0.102(3) 0.0314(15) 0.0392(15) -0.0014(12) 0.0100(16) -0.0062(16) O2 0.0484(16) 0.0658(19) 0.0285(12) -0.0076(13) 0.0095(11) -0.0121(14) N1 0.0456(17) 0.0318(15) 0.0257(13) -0.0020(12) 0.0048(12) 0.0026(14) N4 0.0423(17) 0.0305(15) 0.0237(14) -0.0002(11) 0.0039(12) -0.0032(12) N5 0.055(2) 0.0329(16) 0.0263(14) -0.0013(12) 0.0027(13) 0.0012(14) O4 0.0472(18) 0.121(3) 0.055(2) -0.028(2) 0.0156(16) -0.020(2) O1 0.052(2) 0.097(3) 0.061(2) -0.018(2) 0.0128(16) 0.005(2) N2 0.0541(19) 0.0414(18) 0.0252(14) -0.0038(13) 0.0065(13) 0.0021(15) C8 0.045(2) 0.0315(18) 0.0308(17) -0.0052(14) 0.0095(15) -0.0019(15) N8 0.048(2) 0.075(3) 0.045(2) -0.009(2) 0.0104(17) 0.0002(19) N7 0.056(2) 0.082(3) 0.045(2) -0.005(2) 0.0056(18) -0.007(2) N3 0.085(3) 0.047(2) 0.0275(16) 0.0039(14) 0.0106(17) 0.0058(19) C12 0.043(2) 0.0327(18) 0.0263(16) 0.0009(13) 0.0088(14) -0.0049(15) C10 0.050(2) 0.048(2) 0.0225(17) 0.0035(15) 0.0078(15) 0.0061(18) C7 0.047(2) 0.0280(17) 0.0349(19) -0.0003(14) 0.0076(16) -0.0016(15) C4 0.050(2) 0.0337(19) 0.0277(17) -0.0021(14) 0.0062(15) 0.0036(16) C5 0.049(2) 0.0333(19) 0.0282(17) -0.0060(15) 0.0072(15) -0.0011(16) C14 0.045(2) 0.0321(17) 0.0319(17) -0.0057(15) 0.0078(15) -0.0026(16) C11 0.040(2) 0.044(2) 0.0362(19) -0.0011(16) 0.0139(16) -0.0005(16) N6 0.100(3) 0.0400(18) 0.0279(16) 0.0070(15) 0.0110(17) 0.004(2) C13 0.045(2) 0.0342(19) 0.0284(16) -0.0045(14) 0.0038(14) -0.0024(16) C3 0.044(2) 0.054(2) 0.0314(18) 0.0006(16) 0.0028(16) 0.0005(18) C2 0.059(2) 0.047(2) 0.0249(16) 0.0012(16) 0.0116(16) -0.006(2) C15 0.051(2) 0.0285(18) 0.0336(19) 0.0009(14) 0.0117(16) 0.0019(16) N9 0.069(3) 0.046(2) 0.047(2) 0.001(2) 0.012(2) 0.000(2) C22 0.060(3) 0.067(3) 0.054(3) 0.006(2) 0.017(2) -0.001(2) C6 0.042(2) 0.0364(19) 0.0279(17) 0.0009(14) 0.0041(15) -0.0062(15) C1 0.050(2) 0.057(3) 0.044(2) -0.0017(19) 0.0135(19) 0.002(2) C9 0.050(3) 0.103(4) 0.039(2) -0.001(3) -0.002(2) 0.009(3) C17 0.059(3) 0.068(3) 0.054(3) -0.014(2) 0.009(2) 0.003(2) C23 0.061(3) 0.058(3) 0.058(3) -0.013(2) 0.012(2) -0.001(2) C16 0.043(2) 0.040(2) 0.0300(18) -0.0007(15) 0.0059(15) 0.0069(16) C26 0.059(3) 0.056(3) 0.063(3) -0.011(2) 0.012(2) -0.009(2) C18 0.060(3) 0.070(3) 0.051(3) 0.000(2) 0.007(2) 0.002(2) C19 0.046(2) 0.065(3) 0.041(2) -0.002(2) 0.0024(18) -0.007(2) C24 0.045(2) 0.069(3) 0.041(2) -0.001(2) 0.0061(18) 0.004(2) C21 0.062(3) 0.071(4) 0.052(3) 0.008(2) -0.003(2) -0.012(3) C20 0.055(3) 0.059(3) 0.065(3) -0.010(2) 0.006(2) -0.010(2) N10 0.078(3) 0.052(3) 0.046(3) 0.001(2) 0.010(2) -0.006(2) C25 0.072(3) 0.062(3) 0.054(3) 0.004(2) 0.014(2) -0.008(3) N10B 0.078(3) 0.052(3) 0.046(3) 0.001(2) 0.010(2) -0.006(2) N9B 0.069(3) 0.046(2) 0.047(2) 0.001(2) 0.012(2) 0.000(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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' S S 0.1246 0.1234 '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 C11 S2 C10 87.54(18) . . ? C3 S1 C2 89.17(17) . . ? C10 O5 C12 112.3(3) . . ? C4 O2 C2 114.4(3) . . ? C8 N1 C4 119.8(3) . . ? C8 N1 C5 120.4(3) . . ? C5 N1 C4 119.6(3) . . ? C14 N4 C12 121.3(3) . . ? C14 N4 C13 120.9(3) . . ? C13 N4 C12 117.5(3) . . ? C16 N5 C13 121.4(3) . . ? C9 O4 H4A 109.5 . . ? C1 O1 H1 109.5 . . ? C6 N2 C5 122.0(3) . . ? N1 C8 H8 120.0 . . ? C7 C8 N1 120.0(3) . . ? C7 C8 H8 120.0 . . ? C26 N8 C22 116.8(4) . . ? C17 N7 C21 117.4(4) . . ? H3A N3 H3B 120.0 . . ? C6 N3 H3A 120.0 . . ? C6 N3 H3B 120.0 . . ? O5 C12 N4 107.7(3) . . ? O5 C12 H12 108.4 . . ? O5 C12 C11 109.5(3) . . ? N4 C12 H12 108.4 . . ? N4 C12 C11 114.4(3) . . ? C11 C12 H12 108.4 . . ? S2 C10 H10 108.9 . . ? O5 C10 S2 105.6(2) . . ? O5 C10 H10 108.9 . . ? O5 C10 C9 110.0(3) . . ? C9 C10 S2 114.3(4) . . ? C9 C10 H10 108.9 . . ? F1 C7 C6 118.6(3) . . ? C8 C7 F1 121.4(3) . . ? C8 C7 C6 120.0(3) . . ? O2 C4 N1 107.7(3) . . ? O2 C4 H4 108.7 . . ? O2 C4 C3 108.4(3) . . ? N1 C4 H4 108.7 . . ? N1 C4 C3 114.6(3) . . ? C3 C4 H4 108.7 . . ? O3 C5 N1 119.4(3) . . ? O3 C5 N2 122.5(3) . . ? N2 C5 N1 118.1(3) . . ? N4 C14 H14 120.5 . . ? C15 C14 N4 118.9(3) . . ? C15 C14 H14 120.5 . . ? S2 C11 H11A 110.6 . . ? S2 C11 H11B 110.6 . . ? C12 C11 S2 105.9(3) . . ? C12 C11 H11A 110.6 . . ? C12 C11 H11B 110.6 . . ? H11A C11 H11B 108.7 . . ? H6A N6 H6B 120.0 . . ? C16 N6 H6A 120.0 . . ? C16 N6 H6B 120.0 . . ? O6 C13 N4 119.7(3) . . ? O6 C13 N5 122.5(3) . . ? N5 C13 N4 117.8(3) . . ? S1 C3 H3C 111.0 . . ? S1 C3 H3D 111.0 . . ? C4 C3 S1 103.8(3) . . ? C4 C3 H3C 111.0 . . ? C4 C3 H3D 111.0 . . ? H3C C3 H3D 109.0 . . ? S1 C2 H2 108.8 . . ? O2 C2 S1 107.1(3) . . ? O2 C2 H2 108.8 . . ? O2 C2 C1 110.2(3) . . ? C1 C2 S1 113.0(3) . . ? C1 C2 H2 108.8 . . ? F2 C15 C16 118.3(3) . . ? C14 C15 F2 120.9(3) . . ? C14 C15 C16 120.8(4) . . ? N10 N9 C19 111.9(4) . . ? N8 C22 H22 118.0 . . ? N8 C22 C23 124.1(5) . . ? C23 C22 H22 118.0 . . ? N2 C6 C7 119.2(3) . . ? N3 C6 N2 119.3(4) . . ? N3 C6 C7 121.5(4) . . ? O1 C1 C2 112.0(4) . . ? O1 C1 H1A 109.2 . . ? O1 C1 H1B 109.2 . . ? C2 C1 H1A 109.2 . . ? C2 C1 H1B 109.2 . . ? H1A C1 H1B 107.9 . . ? O4 C9 C10 115.4(4) . . ? O4 C9 H9 122.3 . . ? C10 C9 H9 122.3 . . ? N7 C17 H17 118.0 . . ? N7 C17 C18 124.0(5) . . ? C18 C17 H17 118.0 . . ? C22 C23 H23 121.4 . . ? C22 C23 C24 117.2(5) . . ? C24 C23 H23 121.4 . . ? N5 C16 N6 119.8(4) . . ? N5 C16 C15 120.0(3) . . ? N6 C16 C15 120.3(4) . . ? N8 C26 H26 117.8 . . ? N8 C26 C25 124.3(5) . . ? C25 C26 H26 117.8 . . ? C17 C18 H18 120.9 . . ? C17 C18 C19 118.2(5) . . ? C19 C18 H18 120.9 . . ? C18 C19 N9 114.6(4) . . ? C18 C19 C20 119.6(4) . . ? C18 C19 N9B 149.3(16) . . ? C20 C19 N9 125.7(5) . . ? C20 C19 N9B 89.9(15) . . ? C23 C24 N10 125.7(5) . . ? C23 C24 N10B 90.1(14) . . ? C25 C24 C23 118.9(4) . . ? C25 C24 N10 115.4(4) . . ? C25 C24 N10B 151.0(14) . . ? N7 C21 H21 118.5 . . ? N7 C21 C20 123.1(5) . . ? C20 C21 H21 118.5 . . ? C19 C20 H20 121.1 . . ? C21 C20 C19 117.7(5) . . ? C21 C20 H20 121.1 . . ? N9 N10 C24 112.5(4) . . ? C26 C25 C24 118.7(5) . . ? C26 C25 H25 120.7 . . ? C24 C25 H25 120.7 . . ? N9B N10B C24 112(3) . . ? N10B N9B C19 111(2) . . ? 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 S2 C10 1.811(4) . ? S2 C11 1.801(4) . ? S1 C3 1.799(4) . ? S1 C2 1.824(4) . ? F1 C7 1.354(4) . ? F2 C15 1.359(4) . ? O5 C12 1.429(5) . ? O5 C10 1.420(4) . ? O3 C5 1.221(5) . ? O6 C13 1.212(5) . ? O2 C4 1.428(5) . ? O2 C2 1.428(4) . ? N1 C8 1.367(5) . ? N1 C4 1.455(4) . ? N1 C5 1.412(4) . ? N4 C12 1.462(4) . ? N4 C14 1.369(5) . ? N4 C13 1.411(4) . ? N5 C13 1.371(5) . ? N5 C16 1.314(5) . ? O4 H4A 0.8200 . ? O4 C9 1.399(7) . ? O1 H1 0.8200 . ? O1 C1 1.402(6) . ? N2 C5 1.358(5) . ? N2 C6 1.328(5) . ? C8 H8 0.9300 . ? C8 C7 1.332(5) . ? N8 C22 1.331(7) . ? N8 C26 1.320(7) . ? N7 C17 1.320(7) . ? N7 C21 1.345(7) . ? N3 H3A 0.8600 . ? N3 H3B 0.8600 . ? N3 C6 1.322(5) . ? C12 H12 0.9800 . ? C12 C11 1.535(5) . ? C10 H10 0.9800 . ? C10 C9 1.489(6) . ? C7 C6 1.429(5) . ? C4 H4 0.9800 . ? C4 C3 1.501(5) . ? C14 H14 0.9300 . ? C14 C15 1.327(5) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? N6 H6A 0.8600 . ? N6 H6B 0.8600 . ? N6 C16 1.333(5) . ? C3 H3C 0.9700 . ? C3 H3D 0.9700 . ? C2 H2 0.9800 . ? C2 C1 1.520(6) . ? C15 C16 1.418(5) . ? N9 C19 1.458(6) . ? N9 N10 1.203(6) . ? C22 H22 0.9300 . ? C22 C23 1.388(7) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C9 H9 0.9300 . ? C17 H17 0.9300 . ? C17 C18 1.370(7) . ? C23 H23 0.9300 . ? C23 C24 1.391(7) . ? C26 H26 0.9300 . ? C26 C25 1.366(7) . ? C18 H18 0.9300 . ? C18 C19 1.376(7) . ? C19 C20 1.383(7) . ? C19 N9B 1.45(2) . ? C24 N10 1.448(6) . ? C24 C25 1.376(7) . ? C24 N10B 1.48(2) . ? C21 H21 0.9300 . ? C21 C20 1.382(7) . ? C20 H20 0.9300 . ? C25 H25 0.9300 . ? N10B N9B 1.20(3) . ? 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 S2 C10 C9 O4 -46.1(5) . . . . ? S1 C2 C1 O1 173.1(3) . . . . ? F1 C7 C6 N2 176.6(3) . . . . ? F1 C7 C6 N3 -3.8(6) . . . . ? F2 C15 C16 N5 176.8(4) . . . . ? F2 C15 C16 N6 -2.5(6) . . . . ? O5 C12 C11 S2 19.4(3) . . . . ? O5 C10 C9 O4 72.5(5) . . . . ? O2 C4 C3 S1 -39.3(4) . . . . ? O2 C2 C1 O1 -67.0(5) . . . . ? N1 C8 C7 F1 -178.2(3) . . . . ? N1 C8 C7 C6 1.7(6) . . . . ? N1 C4 C3 S1 -159.7(3) . . . . ? N4 C12 C11 S2 -101.6(3) . . . . ? N4 C14 C15 F2 179.9(4) . . . . ? N4 C14 C15 C16 -0.3(6) . . . . ? C8 N1 C4 O2 -57.0(4) . . . . ? C8 N1 C4 C3 63.7(5) . . . . ? C8 N1 C5 O3 176.9(4) . . . . ? C8 N1 C5 N2 -3.9(5) . . . . ? C8 C7 C6 N2 -3.3(6) . . . . ? C8 C7 C6 N3 176.3(4) . . . . ? N8 C22 C23 C24 -0.2(8) . . . . ? N8 C26 C25 C24 -1.3(8) . . . . ? N7 C17 C18 C19 0.5(8) . . . . ? N7 C21 C20 C19 1.1(8) . . . . ? C12 O5 C10 S2 -37.0(4) . . . . ? C12 O5 C10 C9 -160.9(4) . . . . ? C12 N4 C14 C15 177.3(3) . . . . ? C12 N4 C13 O6 1.1(5) . . . . ? C12 N4 C13 N5 -178.4(3) . . . . ? C10 S2 C11 C12 -33.7(3) . . . . ? C10 O5 C12 N4 136.4(3) . . . . ? C10 O5 C12 C11 11.5(4) . . . . ? C4 O2 C2 S1 8.3(4) . . . . ? C4 O2 C2 C1 -115.0(4) . . . . ? C4 N1 C8 C7 177.7(4) . . . . ? C4 N1 C5 O3 1.0(6) . . . . ? C4 N1 C5 N2 -179.7(3) . . . . ? C5 N1 C8 C7 1.9(5) . . . . ? C5 N1 C4 O2 118.8(4) . . . . ? C5 N1 C4 C3 -120.4(4) . . . . ? C5 N2 C6 N3 -178.3(4) . . . . ? C5 N2 C6 C7 1.2(6) . . . . ? C14 N4 C12 O5 -81.2(4) . . . . ? C14 N4 C12 C11 40.8(5) . . . . ? C14 N4 C13 O6 174.2(4) . . . . ? C14 N4 C13 N5 -5.3(5) . . . . ? C14 C15 C16 N5 -3.0(6) . . . . ? C14 C15 C16 N6 177.7(4) . . . . ? C11 S2 C10 O5 40.8(3) . . . . ? C11 S2 C10 C9 161.9(3) . . . . ? C13 N4 C12 O5 91.9(4) . . . . ? C13 N4 C12 C11 -146.1(3) . . . . ? C13 N4 C14 C15 4.4(6) . . . . ? C13 N5 C16 N6 -178.7(4) . . . . ? C13 N5 C16 C15 2.0(6) . . . . ? C3 S1 C2 O2 -27.1(3) . . . . ? C3 S1 C2 C1 94.4(3) . . . . ? C2 S1 C3 C4 37.4(3) . . . . ? C2 O2 C4 N1 144.9(3) . . . . ? C2 O2 C4 C3 20.3(4) . . . . ? N9 C19 C20 C21 -176.7(5) . . . . ? C22 N8 C26 C25 0.6(8) . . . . ? C22 C23 C24 N10 -179.5(5) . . . . ? C22 C23 C24 C25 -0.5(7) . . . . ? C22 C23 C24 N10B 179(2) . . . . ? C6 N2 C5 O3 -178.5(4) . . . . ? C6 N2 C5 N1 2.3(6) . . . . ? C17 N7 C21 C20 -1.7(8) . . . . ? C17 C18 C19 N9 176.3(5) . . . . ? C17 C18 C19 C20 -1.0(7) . . . . ? C17 C18 C19 N9B -163(3) . . . . ? C23 C24 N10 N9 -13.9(8) . . . . ? C23 C24 C25 C26 1.2(7) . . . . ? C23 C24 N10B N9B -179(4) . . . . ? C16 N5 C13 O6 -177.5(4) . . . . ? C16 N5 C13 N4 2.0(5) . . . . ? C26 N8 C22 C23 0.2(7) . . . . ? C18 C19 C20 C21 0.3(7) . . . . ? C18 C19 N9B N10B -42(6) . . . . ? C19 N9 N10 C24 178.5(4) . . . . ? C24 N10B N9B C19 174(3) . . . . ? C21 N7 C17 C18 0.8(8) . . . . ? C20 C19 N9B N10B 154(4) . . . . ? N10 N9 C19 C18 164.3(5) . . . . ? N10 N9 C19 C20 -18.6(7) . . . . ? N10 C24 C25 C26 -179.7(5) . . . . ? C25 C24 N10 N9 167.0(5) . . . . ? C25 C24 N10B N9B 0(7) . . . . ? N10B C24 C25 C26 -178(4) . . . . ? N9B C19 C20 C21 171.0(18) . . . . ?