#------------------------------------------------------------------------------ #$Date: 2020-05-07 00:20:09 +0300 (Thu, 07 May 2020) $ #$Revision: 251830 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240471.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_7240471 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_absolute_configuration syn _chemical_formula_moiety '2(C8 H10 F N3 O3 S), C12 H12 N2' _chemical_formula_sum 'C28 H32 F2 N8 O6 S2' _chemical_formula_weight 678.73 _chemical_name_systematic '[4-amino-5-fluoro-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1H)-one]-[1,2-Bis(4-pyridyl)ethane]' _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 mixed _atom_sites_solution_primary dual _audit_creation_date 2019-10-13 _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 99.640(5) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 7.6333(8) _cell_length_b 11.2359(11) _cell_length_c 18.1058(18) _cell_measurement_reflns_used 6823 _cell_measurement_temperature 296.15 _cell_measurement_theta_max 28.22 _cell_measurement_theta_min 2.9145 _cell_volume 1531.0(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 0.987 _diffrn_measured_fraction_theta_max 0.987 _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 0.0313 _diffrn_reflns_av_unetI/netI 0.0339 _diffrn_reflns_Laue_measured_fraction_full 0.987 _diffrn_reflns_Laue_measured_fraction_max 0.987 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 15295 _diffrn_reflns_point_group_measured_fraction_full 0.981 _diffrn_reflns_point_group_measured_fraction_max 0.981 _diffrn_reflns_theta_full 24.997 _diffrn_reflns_theta_max 24.997 _diffrn_reflns_theta_min 2.756 _exptl_absorpt_coefficient_mu 0.243 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_correction_T_min 0.7100 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1097 before and 0.0501 after correction. The Ratio of minimum to maximum transmission is 0.9521. The \l/2 correction factor is Not present.' _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.472 _exptl_crystal_description needle _exptl_crystal_F_000 708 _exptl_crystal_size_max 0.185 _exptl_crystal_size_mid 0.055 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.140 _refine_diff_density_min -0.150 _refine_diff_density_rms 0.027 _refine_ls_abs_structure_details ; Flack x determined using 2112 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.02(3) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 446 _refine_ls_number_reflns 5271 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.023 _refine_ls_R_factor_all 0.0325 _refine_ls_R_factor_gt 0.0292 _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^)+(0.0316P)^2^+0.2269P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0677 _refine_ls_wR_factor_ref 0.0700 _reflns_Friedel_coverage 0.881 _reflns_Friedel_fraction_full 0.974 _reflns_Friedel_fraction_max 0.974 _reflns_number_gt 4924 _reflns_number_total 5271 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ce00474j2.cif _cod_data_source_block FTC-bpeta _cod_database_code 7240471 _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 0.988 _shelx_estimated_absorpt_t_min 0.956 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups 2. Uiso/Uaniso restraints and constraints Uanis(C22A) = Uanis(C22B) Uanis(C23A) = Uanis(C23B) 3. Others Sof(C23B)=Sof(H23A)=Sof(H23B)=Sof(C22B)=Sof(H22A)=Sof(H22B)=1-FVAR(1) Sof(C22A)=Sof(H22C)=Sof(H22D)=Sof(C23A)=Sof(H23C)=Sof(H23D)=FVAR(1) 4.a Ternary CH refined with riding coordinates: C12(H12), C2(H2), C10(H10), C4(H4) 4.b Secondary CH2 refined with riding coordinates: C11(H11A,H11B), C1(H1A,H1B), C3(H3C,H3D), C9(H9A,H9B), C23B(H23A,H23B), C22B(H22A,H22B), C22A(H22C,H22D), C23A(H23C,H23D) 4.c Aromatic/amide H refined with riding coordinates: C8(H8), C16(H16), C24(H24), C21(H21), C20(H20), C17(H17), C18(H18), C27(H27), C25(H25), C28(H28) ; _shelx_res_file ; TITL mcg19125_a.res in P2(1) mcg19125.res created by SHELXL-2016/6 at 14:12:02 on 13-Oct-2019 REM Old TITL Mcg19_125 in P2(1) sample #19181 EMT-bpeta REM SHELXT solution in P2(1) REM R1 0.136, Rweak 0.036, Alpha 0.005, Orientation as input REM Flack x = 0.061 ( 0.026 ) from Parsons' quotients REM Formula found by SHELXT: C30 F3 N6 O5 S2 CELL 0.71073 7.6333 11.2359 18.1058 90 99.64 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 56 64 4 16 12 4 EADP C22A C22B EADP C23A C23B L.S. 15 PLAN 20 SIZE 0.05 0.055 0.185 TEMP 23 BOND $H HTAB CONF list 4 fmap 2 acta OMIT -2 50 REM REM REM WGHT 0.031600 0.226900 FVAR 1.47195 0.76234 S1 6 1.048100 0.445799 0.692733 11.00000 0.05778 0.05520 = 0.02474 0.00318 -0.00076 -0.01412 S2 6 0.783270 0.656460 -0.172545 11.00000 0.05435 0.04444 = 0.03970 0.01519 0.00756 -0.00299 F1 3 0.742045 0.181113 0.367698 11.00000 0.07519 0.02985 = 0.04500 -0.00538 0.00799 -0.00944 F2 3 0.823443 0.819092 0.113801 11.00000 0.10240 0.03227 = 0.04214 -0.00332 0.02427 0.00547 O5 5 0.694759 0.487189 -0.090450 11.00000 0.04384 0.04503 = 0.02657 0.00526 0.00342 -0.01007 O2 5 0.791363 0.469713 0.577304 11.00000 0.04304 0.06257 = 0.02657 0.00937 0.00895 0.00705 O6 5 0.930286 0.361235 0.062299 11.00000 0.09358 0.02991 = 0.03736 0.00241 0.00489 0.00775 O3 5 1.002725 0.615961 0.429143 11.00000 0.09205 0.03428 = 0.03247 0.00086 0.00928 -0.02055 N4 4 0.886515 0.549392 0.016010 11.00000 0.04339 0.02863 = 0.02361 0.00055 0.00421 0.00152 N1 4 0.921797 0.436997 0.472197 11.00000 0.04524 0.03139 = 0.02256 0.00253 0.00662 -0.00319 N2 4 0.917238 0.472597 0.342639 11.00000 0.05452 0.03699 = 0.02411 0.00172 0.00630 -0.00537 O4 5 0.384739 0.639629 -0.158890 11.00000 0.05167 0.09260 = 0.04403 0.01991 0.00951 0.01925 O1 5 0.538717 0.330710 0.649068 11.00000 0.05058 0.08236 = 0.04761 0.01141 0.01170 -0.00834 N5 4 0.910735 0.508167 0.146248 11.00000 0.05462 0.03418 = 0.02387 0.00283 0.00095 -0.00299 N6 4 0.889217 0.659446 0.229035 11.00000 0.08824 0.03847 = 0.02638 -0.00504 0.01025 -0.00647 N8 4 0.376638 0.596166 -0.004400 11.00000 0.05129 0.06419 = 0.03985 0.00568 0.00793 0.00415 C8 1 0.851627 0.325921 0.456410 11.00000 0.04851 0.02960 = 0.02845 0.00414 0.00916 0.00039 AFIX 43 H8 2 0.828894 0.276445 0.494884 11.00000 -1.20000 AFIX 0 C12 1 0.877956 0.504069 -0.060081 11.00000 0.04159 0.03370 = 0.02635 -0.00110 0.00584 0.00474 AFIX 13 H12 2 0.937493 0.426539 -0.057453 11.00000 -1.20000 AFIX 0 N3 4 0.832978 0.325459 0.256324 11.00000 0.07482 0.04220 = 0.02810 -0.00439 0.00983 -0.00693 N7 4 0.408514 0.365750 0.494409 11.00000 0.04990 0.06498 = 0.04389 0.00925 0.00342 -0.00073 C16 1 0.854290 0.666880 0.028577 11.00000 0.04867 0.03250 = 0.02950 0.00629 0.00862 0.00444 AFIX 43 H16 2 0.832642 0.720314 -0.011133 11.00000 -1.20000 AFIX 0 C2 1 0.811317 0.444062 0.655309 11.00000 0.05332 0.03954 = 0.02272 -0.00202 0.01041 0.00081 AFIX 13 H2 2 0.752937 0.506906 0.679822 11.00000 -1.20000 AFIX 0 C7 1 0.816187 0.289295 0.385506 11.00000 0.04399 0.02541 = 0.03537 -0.00063 0.00464 0.00005 C10 1 0.653111 0.523737 -0.166152 11.00000 0.05075 0.03841 = 0.02423 -0.00222 0.00719 -0.00274 AFIX 13 H10 2 0.693439 0.462008 -0.197674 11.00000 -1.20000 AFIX 0 C5 1 0.949309 0.514755 0.414222 11.00000 0.04582 0.03230 = 0.02709 0.00501 0.00510 -0.00100 C11 1 0.963628 0.585440 -0.112206 11.00000 0.03964 0.05042 = 0.03322 -0.00003 0.01156 0.00013 AFIX 23 H11A 2 1.034988 0.539193 -0.141326 11.00000 -1.20000 H11B 2 1.039132 0.644275 -0.083375 11.00000 -1.20000 AFIX 0 C6 1 0.855745 0.363303 0.326739 11.00000 0.04075 0.03662 = 0.02768 -0.00088 0.00422 0.00435 C4 1 0.954470 0.479449 0.549633 11.00000 0.04376 0.03331 = 0.02582 0.00018 0.00882 -0.00346 AFIX 13 H4 2 0.989308 0.563426 0.550045 11.00000 -1.20000 AFIX 0 C13 1 0.910600 0.465857 0.075409 11.00000 0.04308 0.03392 = 0.02874 0.00436 0.00089 0.00233 C1 1 0.724677 0.326645 0.667237 11.00000 0.05176 0.04529 = 0.03389 0.00317 0.00995 -0.00193 AFIX 23 H1A 2 0.769115 0.266385 0.636750 11.00000 -1.20000 H1B 2 0.757842 0.303375 0.719293 11.00000 -1.20000 AFIX 0 C3 1 1.095672 0.410504 0.600873 11.00000 0.04544 0.04770 = 0.02984 0.00244 0.00377 -0.00198 AFIX 23 H3C 2 1.213929 0.436638 0.595393 11.00000 -1.20000 H3D 2 1.085208 0.325719 0.591029 11.00000 -1.20000 AFIX 0 C24 1 0.416692 0.488407 0.025102 11.00000 0.06495 0.05575 = 0.04851 -0.00499 0.01621 0.00054 AFIX 43 H24 2 0.430772 0.426082 -0.007194 11.00000 -1.20000 AFIX 0 C15 1 0.854412 0.703246 0.098060 11.00000 0.04977 0.02758 = 0.03377 -0.00074 0.01065 -0.00184 C19 1 0.356222 0.425625 0.342218 11.00000 0.05057 0.06128 = 0.03988 0.00505 -0.00054 -0.01021 C14 1 0.885598 0.621809 0.158944 11.00000 0.04198 0.03680 = 0.02860 -0.00176 0.00461 -0.00783 C9 1 0.456459 0.539592 -0.189473 11.00000 0.05001 0.07352 = 0.03467 0.00313 -0.00158 -0.00670 AFIX 23 H9A 2 0.430521 0.545420 -0.243658 11.00000 -1.20000 H9B 2 0.397092 0.469046 -0.175097 11.00000 -1.20000 AFIX 0 C21 1 0.440481 0.474580 0.471276 11.00000 0.05170 0.05809 = 0.04432 -0.00730 -0.00205 0.00199 AFIX 43 H21 2 0.480008 0.531692 0.507418 11.00000 -1.20000 AFIX 0 C20 1 0.418780 0.508201 0.397117 11.00000 0.05700 0.04627 = 0.05233 0.00991 -0.00410 -0.00212 AFIX 43 H20 2 0.445781 0.585311 0.384104 11.00000 -1.20000 AFIX 0 C17 1 0.346832 0.287967 0.441090 11.00000 0.05742 0.05109 = 0.05557 0.00675 0.00636 -0.00614 AFIX 43 H17 2 0.320975 0.211450 0.455638 11.00000 -1.20000 AFIX 0 C26 1 0.418529 0.554917 0.150313 11.00000 0.05020 0.07060 = 0.04005 0.00042 0.01132 -0.00387 C18 1 0.319011 0.313298 0.366271 11.00000 0.06204 0.05305 = 0.04907 -0.00664 0.00375 -0.00589 AFIX 43 H18 2 0.275093 0.254996 0.331610 11.00000 -1.20000 AFIX 0 C27 1 0.374901 0.664957 0.119196 11.00000 0.07274 0.05878 = 0.05453 -0.00622 0.01788 0.01064 AFIX 43 H27 2 0.357740 0.728689 0.149972 11.00000 -1.20000 AFIX 0 C25 1 0.438194 0.464817 0.100740 11.00000 0.07109 0.05201 = 0.05648 0.01447 0.01749 0.00592 AFIX 43 H25 2 0.465944 0.388188 0.118318 11.00000 -1.20000 AFIX 0 C28 1 0.356641 0.681398 0.043880 11.00000 0.06364 0.05626 = 0.05925 0.01141 0.01354 0.01362 AFIX 43 H28 2 0.328322 0.757323 0.025153 11.00000 -1.20000 AFIX 0 PART 2 C23B 1 0.460604 0.486886 0.231524 -21.00000 0.07453 0.03386 = 0.04549 0.00188 0.01107 0.00020 AFIX 23 H23A 2 0.495480 0.405229 0.224384 -21.00000 -1.20000 H23B 2 0.557907 0.526391 0.263563 -21.00000 -1.20000 AFIX 0 C22B 1 0.319154 0.488578 0.263138 -21.00000 0.09808 0.10530 = 0.04389 0.01496 -0.01018 -0.06335 AFIX 23 H22A 2 0.222652 0.448126 0.231202 -21.00000 -1.20000 H22B 2 0.283237 0.570336 0.269154 -21.00000 -1.20000 AFIX 0 PART 0 H3A 2 0.858712 0.374136 0.222609 11.00000 0.05014 H4A 2 0.386392 0.631630 -0.114696 11.00000 0.07849 H6A 2 0.912878 0.604666 0.266512 11.00000 0.06958 H1 2 0.502081 0.346026 0.605110 11.00000 0.10304 H3B 2 0.791163 0.255238 0.243656 11.00000 0.05275 PART 1 C22A 1 0.326685 0.448781 0.259321 21.00000 0.09808 0.10530 = 0.04389 0.01496 -0.01018 -0.06335 AFIX 23 H22C 2 0.203795 0.472080 0.243424 21.00000 -1.20000 H22D 2 0.345509 0.375160 0.233786 21.00000 -1.20000 AFIX 0 C23A 1 0.445857 0.544288 0.234786 21.00000 0.07453 0.03386 = 0.04549 0.00188 0.01107 0.00020 AFIX 23 H23C 2 0.420034 0.620131 0.256197 21.00000 -1.20000 H23D 2 0.569112 0.524812 0.253468 21.00000 -1.20000 AFIX 0 PART 0 H6B 2 0.878124 0.729298 0.237034 11.00000 0.07526 HKLF 4 REM mcg19125_a.res in P2(1) REM R1 = 0.0292 for 4924 Fo > 4sig(Fo) and 0.0325 for all 5271 data REM 446 parameters refined using 1 restraints END WGHT 0.0316 0.2269 REM Instructions for potential hydrogen bonds EQIV $1 -x+2, y-1/2, -z+1 HTAB C8 O3_$1 EQIV $2 -x+2, y-1/2, -z HTAB C12 F2_$2 HTAB C16 S2 EQIV $3 -x+2, y+1/2, -z HTAB C11 O6_$3 EQIV $4 x+1, y, z HTAB C3 N7_$4 HTAB C3 O3_$1 EQIV $5 -x+1, y+1/2, -z HTAB C28 O6_$5 HTAB N3 N5 HTAB O4 N8 HTAB N6 N2 HTAB O1 N7 EQIV $6 -x+1, y-1/2, -z HTAB N3 O4_$6 EQIV $7 -x+2, y+1/2, -z+1 HTAB N6 S1_$7 REM Highest difference peak 0.140, deepest hole -0.150, 1-sigma level 0.027 Q1 1 0.2220 0.4046 0.2299 11.00000 0.05 0.14 Q2 1 0.9221 0.4432 0.6698 11.00000 0.05 0.13 Q3 1 1.0928 0.4180 0.6530 11.00000 0.05 0.13 Q4 1 0.3325 0.5875 0.1337 11.00000 0.05 0.12 Q5 1 0.9191 0.5409 -0.0924 11.00000 0.05 0.11 Q6 1 0.8744 0.6089 0.4171 11.00000 0.05 0.11 Q7 1 0.9236 0.6731 0.1320 11.00000 0.05 0.11 Q8 1 0.3309 0.5458 0.2325 11.00000 0.05 0.11 Q9 1 0.7991 0.6643 0.0691 11.00000 0.05 0.10 Q10 1 0.8469 0.4900 0.4485 11.00000 0.05 0.10 Q11 1 0.8943 0.4472 0.1717 11.00000 0.05 0.10 Q12 1 0.9283 0.7020 0.0654 11.00000 0.05 0.10 Q13 1 0.3662 0.4880 0.1318 11.00000 0.05 0.10 Q14 1 0.7972 0.4529 -0.0826 11.00000 0.05 0.10 Q15 1 0.8775 0.2865 0.7787 11.00000 0.05 0.10 Q16 1 0.5998 0.4579 0.5839 11.00000 0.05 0.10 Q17 1 0.8721 0.2986 0.4219 11.00000 0.05 0.10 Q18 1 0.4634 0.5039 0.2791 11.00000 0.05 0.09 Q19 1 0.9721 0.4631 0.4527 11.00000 0.05 0.09 Q20 1 0.8261 0.3922 0.0681 11.00000 0.05 0.09 ; _shelx_res_checksum 3499 _olex2_submission_original_sample_id EMT-bpeta _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 S1 S 1.04810(11) 0.44580(8) 0.69273(4) 0.0468(2) Uani 1 1 d . . . . . S2 S 0.78327(11) 0.65646(7) -0.17255(4) 0.0462(2) Uani 1 1 d . . . . . F1 F 0.7420(3) 0.18111(15) 0.36770(10) 0.0503(5) Uani 1 1 d . . . . . F2 F 0.8234(3) 0.81909(16) 0.11380(10) 0.0575(5) Uani 1 1 d . . . . . O5 O 0.6948(3) 0.48719(18) -0.09045(10) 0.0388(5) Uani 1 1 d . . . . . O2 O 0.7914(3) 0.4697(2) 0.57730(10) 0.0437(5) Uani 1 1 d . . . . . O6 O 0.9303(4) 0.36123(19) 0.06230(12) 0.0543(6) Uani 1 1 d . . . . . O3 O 1.0027(3) 0.61596(19) 0.42914(11) 0.0531(6) Uani 1 1 d . . . . . N4 N 0.8865(3) 0.5494(2) 0.01601(12) 0.0320(5) Uani 1 1 d . . . . . N1 N 0.9218(3) 0.4370(2) 0.47220(11) 0.0330(5) Uani 1 1 d . . . . . N2 N 0.9172(3) 0.4726(2) 0.34264(12) 0.0386(6) Uani 1 1 d . . . . . O4 O 0.3847(3) 0.6396(3) -0.15889(15) 0.0626(7) Uani 1 1 d . . . . . O1 O 0.5387(3) 0.3307(3) 0.64907(16) 0.0598(7) Uani 1 1 d . . . . . N5 N 0.9107(3) 0.5082(2) 0.14625(12) 0.0382(6) Uani 1 1 d . . . . . N6 N 0.8892(5) 0.6594(3) 0.22904(15) 0.0510(7) Uani 1 1 d . . . . . N8 N 0.3766(4) 0.5962(3) -0.00440(15) 0.0517(7) Uani 1 1 d . . . . . C8 C 0.8516(4) 0.3259(3) 0.45641(15) 0.0352(6) Uani 1 1 d . . . . . H8 H 0.828894 0.276445 0.494884 0.042 Uiso 1 1 calc R . . . . C12 C 0.8780(4) 0.5041(3) -0.06008(14) 0.0339(6) Uani 1 1 d . . . . . H12 H 0.937493 0.426539 -0.057453 0.041 Uiso 1 1 calc R . . . . N3 N 0.8330(4) 0.3255(3) 0.25632(15) 0.0482(7) Uani 1 1 d . . . . . N7 N 0.4085(4) 0.3658(3) 0.49441(15) 0.0534(7) Uani 1 1 d . . . . . C16 C 0.8543(4) 0.6669(3) 0.02858(15) 0.0367(6) Uani 1 1 d . . . . . H16 H 0.832642 0.720314 -0.011133 0.044 Uiso 1 1 calc R . . . . C2 C 0.8113(4) 0.4441(3) 0.65531(14) 0.0381(6) Uani 1 1 d . . . . . H2 H 0.752937 0.506906 0.679822 0.046 Uiso 1 1 calc R . . . . C7 C 0.8162(4) 0.2893(2) 0.38551(16) 0.0352(6) Uani 1 1 d . . . . . C10 C 0.6531(4) 0.5237(3) -0.16615(14) 0.0377(6) Uani 1 1 d . . . . . H10 H 0.693439 0.462008 -0.197674 0.045 Uiso 1 1 calc R . . . . C5 C 0.9493(4) 0.5148(3) 0.41422(14) 0.0352(6) Uani 1 1 d . . . . . C11 C 0.9636(4) 0.5854(3) -0.11221(16) 0.0405(7) Uani 1 1 d . . . . . H11A H 1.034988 0.539193 -0.141326 0.049 Uiso 1 1 calc R . . . . H11B H 1.039132 0.644275 -0.083375 0.049 Uiso 1 1 calc R . . . . C6 C 0.8557(4) 0.3633(3) 0.32674(15) 0.0352(6) Uani 1 1 d . . . . . C4 C 0.9545(4) 0.4794(3) 0.54963(14) 0.0340(6) Uani 1 1 d . . . . . H4 H 0.989308 0.563426 0.550045 0.041 Uiso 1 1 calc R . . . . C13 C 0.9106(4) 0.4659(3) 0.07541(14) 0.0358(6) Uani 1 1 d . . . . . C1 C 0.7247(4) 0.3266(3) 0.66724(17) 0.0433(7) Uani 1 1 d . . . . . H1A H 0.769115 0.266385 0.636750 0.052 Uiso 1 1 calc R . . . . H1B H 0.757842 0.303375 0.719293 0.052 Uiso 1 1 calc R . . . . C3 C 1.0957(4) 0.4105(3) 0.60087(15) 0.0413(7) Uani 1 1 d . . . . . H3C H 1.213929 0.436638 0.595393 0.050 Uiso 1 1 calc R . . . . H3D H 1.085208 0.325719 0.591029 0.050 Uiso 1 1 calc R . . . . C24 C 0.4167(5) 0.4884(3) 0.02510(19) 0.0556(9) Uani 1 1 d . . . . . H24 H 0.430772 0.426082 -0.007194 0.067 Uiso 1 1 calc R . . . . C15 C 0.8544(4) 0.7032(3) 0.09806(16) 0.0366(6) Uani 1 1 d . . . . . C19 C 0.3562(4) 0.4256(3) 0.34222(17) 0.0515(8) Uani 1 1 d . . . . . C14 C 0.8856(4) 0.6218(3) 0.15894(15) 0.0359(6) Uani 1 1 d . . . . . C9 C 0.4565(4) 0.5396(4) -0.18947(17) 0.0537(9) Uani 1 1 d . . . . . H9A H 0.430521 0.545420 -0.243658 0.064 Uiso 1 1 calc R . . . . H9B H 0.397092 0.469046 -0.175097 0.064 Uiso 1 1 calc R . . . . C21 C 0.4405(4) 0.4746(3) 0.47128(18) 0.0525(8) Uani 1 1 d . . . . . H21 H 0.480008 0.531692 0.507418 0.063 Uiso 1 1 calc R . . . . C20 C 0.4188(5) 0.5082(3) 0.39712(19) 0.0534(9) Uani 1 1 d . . . . . H20 H 0.445781 0.585311 0.384104 0.064 Uiso 1 1 calc R . . . . C17 C 0.3468(5) 0.2880(4) 0.4411(2) 0.0550(9) Uani 1 1 d . . . . . H17 H 0.320975 0.211450 0.455638 0.066 Uiso 1 1 calc R . . . . C26 C 0.4185(5) 0.5549(4) 0.15031(18) 0.0532(9) Uani 1 1 d . . . . . C18 C 0.3190(5) 0.3133(3) 0.3663(2) 0.0554(9) Uani 1 1 d . . . . . H18 H 0.275093 0.254996 0.331610 0.066 Uiso 1 1 calc R . . . . C27 C 0.3749(5) 0.6650(4) 0.1192(2) 0.0612(9) Uani 1 1 d . . . . . H27 H 0.357740 0.728689 0.149972 0.073 Uiso 1 1 calc R . . . . C25 C 0.4382(5) 0.4648(4) 0.1007(2) 0.0591(9) Uani 1 1 d . . . . . H25 H 0.465944 0.388188 0.118318 0.071 Uiso 1 1 calc R . . . . C28 C 0.3566(5) 0.6814(4) 0.0439(2) 0.0593(9) Uani 1 1 d . . . . . H28 H 0.328322 0.757323 0.025153 0.071 Uiso 1 1 calc R . . . . C23B C 0.461(3) 0.487(2) 0.2315(10) 0.0512(14) Uani 0.238(14) 1 d . . P A 2 H23A H 0.495480 0.405229 0.224384 0.061 Uiso 0.238(14) 1 calc R . P A 2 H23B H 0.557907 0.526391 0.263563 0.061 Uiso 0.238(14) 1 calc R . P A 2 C22B C 0.319(9) 0.489(5) 0.263(3) 0.085(4) Uani 0.238(14) 1 d . . P A 2 H22A H 0.222652 0.448126 0.231202 0.102 Uiso 0.238(14) 1 calc R . P A 2 H22B H 0.283237 0.570336 0.269154 0.102 Uiso 0.238(14) 1 calc R . P A 2 H3A H 0.859(5) 0.374(3) 0.223(2) 0.050(10) Uiso 1 1 d . . . . . H4A H 0.386(6) 0.632(4) -0.115(3) 0.078(14) Uiso 1 1 d . . . . . H6A H 0.913(5) 0.605(4) 0.267(2) 0.070(12) Uiso 1 1 d . . . . . H1 H 0.502(7) 0.346(5) 0.605(3) 0.103(19) Uiso 1 1 d . . . . . H3B H 0.791(5) 0.255(4) 0.244(2) 0.053(11) Uiso 1 1 d . . . . . C22A C 0.327(3) 0.4488(11) 0.2593(8) 0.085(4) Uani 0.762(14) 1 d . . P A 1 H22C H 0.203795 0.472080 0.243424 0.102 Uiso 0.762(14) 1 calc R . P A 1 H22D H 0.345509 0.375160 0.233786 0.102 Uiso 0.762(14) 1 calc R . P A 1 C23A C 0.4459(8) 0.5443(7) 0.2348(3) 0.0512(14) Uani 0.762(14) 1 d . . P A 1 H23C H 0.420034 0.620131 0.256197 0.061 Uiso 0.762(14) 1 calc R . P A 1 H23D H 0.569112 0.524812 0.253468 0.061 Uiso 0.762(14) 1 calc R . P A 1 H6B H 0.878(6) 0.729(4) 0.237(2) 0.075(14) Uiso 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0578(5) 0.0552(5) 0.0247(3) 0.0032(3) -0.0008(3) -0.0141(4) S2 0.0543(5) 0.0444(5) 0.0397(4) 0.0152(3) 0.0076(3) -0.0030(4) F1 0.0752(12) 0.0298(10) 0.0450(10) -0.0054(8) 0.0080(8) -0.0094(9) F2 0.1024(16) 0.0323(10) 0.0421(10) -0.0033(8) 0.0243(10) 0.0055(10) O5 0.0438(11) 0.0450(13) 0.0266(9) 0.0053(8) 0.0034(8) -0.0101(9) O2 0.0430(11) 0.0626(15) 0.0266(9) 0.0094(9) 0.0089(8) 0.0070(11) O6 0.0936(18) 0.0299(13) 0.0374(12) 0.0024(9) 0.0049(11) 0.0078(11) O3 0.0921(18) 0.0343(13) 0.0325(11) 0.0009(9) 0.0093(11) -0.0206(12) N4 0.0434(13) 0.0286(13) 0.0236(11) 0.0005(9) 0.0042(9) 0.0015(10) N1 0.0452(13) 0.0314(13) 0.0226(10) 0.0025(10) 0.0066(9) -0.0032(11) N2 0.0545(14) 0.0370(14) 0.0241(11) 0.0017(10) 0.0063(10) -0.0054(11) O4 0.0517(14) 0.093(2) 0.0440(14) 0.0199(14) 0.0095(11) 0.0192(14) O1 0.0506(14) 0.0824(19) 0.0476(15) 0.0114(13) 0.0117(11) -0.0083(13) N5 0.0546(15) 0.0342(14) 0.0239(11) 0.0028(10) 0.0009(10) -0.0030(11) N6 0.088(2) 0.0385(17) 0.0264(13) -0.0050(12) 0.0102(13) -0.0065(16) N8 0.0513(16) 0.064(2) 0.0398(15) 0.0057(14) 0.0079(12) 0.0041(14) C8 0.0485(17) 0.0296(15) 0.0284(14) 0.0041(11) 0.0092(12) 0.0004(13) C12 0.0416(15) 0.0337(16) 0.0264(13) -0.0011(11) 0.0058(11) 0.0047(12) N3 0.075(2) 0.0422(17) 0.0281(14) -0.0044(12) 0.0098(13) -0.0069(15) N7 0.0499(16) 0.065(2) 0.0439(16) 0.0092(14) 0.0034(12) -0.0007(14) C16 0.0487(16) 0.0325(15) 0.0295(14) 0.0063(12) 0.0086(11) 0.0044(13) C2 0.0533(17) 0.0395(17) 0.0227(12) -0.0020(12) 0.0104(11) 0.0008(14) C7 0.0440(16) 0.0254(14) 0.0354(15) -0.0006(12) 0.0046(12) 0.0000(12) C10 0.0507(17) 0.0384(16) 0.0242(13) -0.0022(12) 0.0072(12) -0.0027(14) C5 0.0458(16) 0.0323(16) 0.0271(13) 0.0050(11) 0.0051(11) -0.0010(13) C11 0.0396(15) 0.0504(19) 0.0332(15) 0.0000(13) 0.0116(12) 0.0001(14) C6 0.0407(16) 0.0366(17) 0.0277(14) -0.0009(12) 0.0042(11) 0.0043(13) C4 0.0438(15) 0.0333(16) 0.0258(13) 0.0002(11) 0.0088(11) -0.0035(12) C13 0.0431(15) 0.0339(17) 0.0287(14) 0.0044(12) 0.0009(11) 0.0023(13) C1 0.0518(19) 0.0453(19) 0.0339(16) 0.0032(13) 0.0100(13) -0.0019(15) C3 0.0454(17) 0.0477(19) 0.0298(14) 0.0024(12) 0.0038(12) -0.0020(14) C24 0.065(2) 0.056(2) 0.0485(19) -0.0050(16) 0.0162(16) 0.0005(17) C15 0.0498(17) 0.0276(15) 0.0338(15) -0.0007(11) 0.0106(12) -0.0018(13) C19 0.0506(19) 0.061(2) 0.0399(17) 0.0050(16) -0.0005(14) -0.0102(17) C14 0.0420(16) 0.0368(17) 0.0286(14) -0.0018(11) 0.0046(11) -0.0078(13) C9 0.0500(19) 0.074(3) 0.0347(17) 0.0031(16) -0.0016(14) -0.0067(18) C21 0.0517(19) 0.058(2) 0.0443(18) -0.0073(16) -0.0021(14) 0.0020(17) C20 0.057(2) 0.046(2) 0.052(2) 0.0099(16) -0.0041(15) -0.0021(16) C17 0.057(2) 0.051(2) 0.056(2) 0.0068(17) 0.0064(17) -0.0061(17) C26 0.0502(19) 0.071(3) 0.0400(18) 0.0004(17) 0.0113(14) -0.0039(17) C18 0.062(2) 0.053(2) 0.049(2) -0.0066(16) 0.0037(16) -0.0059(17) C27 0.073(2) 0.059(2) 0.055(2) -0.0062(19) 0.0179(17) 0.011(2) C25 0.071(2) 0.052(2) 0.056(2) 0.0145(18) 0.0175(17) 0.0059(19) C28 0.064(2) 0.056(2) 0.059(2) 0.0114(18) 0.0135(17) 0.0136(19) C23B 0.075(3) 0.034(4) 0.045(2) 0.002(3) 0.0111(19) 0.000(3) C22B 0.098(4) 0.105(10) 0.044(3) 0.015(6) -0.010(3) -0.063(9) C22A 0.098(4) 0.105(10) 0.044(3) 0.015(6) -0.010(3) -0.063(9) C23A 0.075(3) 0.034(4) 0.045(2) 0.002(3) 0.0111(19) 0.000(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 C3 S1 C2 89.72(13) . . ? C11 S2 C10 88.17(14) . . ? C10 O5 C12 112.4(2) . . ? C4 O2 C2 114.2(2) . . ? C16 N4 C12 120.8(2) . . ? C16 N4 C13 121.1(2) . . ? C13 N4 C12 117.7(2) . . ? C8 N1 C5 120.8(2) . . ? C8 N1 C4 119.7(2) . . ? C5 N1 C4 119.3(2) . . ? C6 N2 C5 121.9(2) . . ? C9 O4 H4A 111(3) . . ? C1 O1 H1 114(4) . . ? C14 N5 C13 121.6(2) . . ? C14 N6 H6A 118(3) . . ? C14 N6 H6B 120(3) . . ? H6A N6 H6B 123(4) . . ? C28 N8 C24 115.8(3) . . ? N1 C8 H8 120.3 . . ? C7 C8 N1 119.5(3) . . ? C7 C8 H8 120.3 . . ? O5 C12 N4 107.2(2) . . ? O5 C12 H12 108.5 . . ? O5 C12 C11 109.4(2) . . ? N4 C12 H12 108.5 . . ? N4 C12 C11 114.6(2) . . ? C11 C12 H12 108.5 . . ? C6 N3 H3A 118(2) . . ? C6 N3 H3B 122(2) . . ? H3A N3 H3B 120(3) . . ? C21 N7 C17 116.0(3) . . ? N4 C16 H16 120.5 . . ? C15 C16 N4 119.0(3) . . ? C15 C16 H16 120.5 . . ? S1 C2 H2 108.8 . . ? O2 C2 S1 107.54(18) . . ? O2 C2 H2 108.8 . . ? O2 C2 C1 110.0(2) . . ? C1 C2 S1 112.8(2) . . ? C1 C2 H2 108.8 . . ? F1 C7 C6 118.6(2) . . ? C8 C7 F1 121.0(3) . . ? C8 C7 C6 120.4(3) . . ? S2 C10 H10 108.5 . . ? O5 C10 S2 105.36(18) . . ? O5 C10 H10 108.5 . . ? O5 C10 C9 111.0(2) . . ? C9 C10 S2 114.8(2) . . ? C9 C10 H10 108.5 . . ? O3 C5 N1 119.9(2) . . ? O3 C5 N2 122.2(3) . . ? N2 C5 N1 117.9(3) . . ? S2 C11 H11A 110.5 . . ? S2 C11 H11B 110.5 . . ? C12 C11 S2 106.05(19) . . ? C12 C11 H11A 110.5 . . ? C12 C11 H11B 110.5 . . ? H11A C11 H11B 108.7 . . ? N2 C6 C7 119.3(2) . . ? N3 C6 N2 119.3(3) . . ? N3 C6 C7 121.4(3) . . ? O2 C4 N1 107.1(2) . . ? O2 C4 H4 108.9 . . ? O2 C4 C3 108.7(2) . . ? N1 C4 H4 108.9 . . ? N1 C4 C3 114.2(2) . . ? C3 C4 H4 108.9 . . ? O6 C13 N4 119.9(2) . . ? O6 C13 N5 122.6(3) . . ? N5 C13 N4 117.5(3) . . ? O1 C1 C2 112.9(3) . . ? O1 C1 H1A 109.0 . . ? O1 C1 H1B 109.0 . . ? C2 C1 H1A 109.0 . . ? C2 C1 H1B 109.0 . . ? H1A C1 H1B 107.8 . . ? S1 C3 H3C 111.2 . . ? S1 C3 H3D 111.2 . . ? C4 C3 S1 102.7(2) . . ? C4 C3 H3C 111.2 . . ? C4 C3 H3D 111.2 . . ? H3C C3 H3D 109.1 . . ? N8 C24 H24 118.2 . . ? N8 C24 C25 123.5(3) . . ? C25 C24 H24 118.2 . . ? F2 C15 C14 117.7(2) . . ? C16 C15 F2 121.5(3) . . ? C16 C15 C14 120.8(3) . . ? C20 C19 C22B 109.8(17) . . ? C20 C19 C22A 125.2(5) . . ? C18 C19 C20 116.8(3) . . ? C18 C19 C22B 132.9(17) . . ? C18 C19 C22A 118.0(5) . . ? N5 C14 N6 119.5(3) . . ? N5 C14 C15 119.9(2) . . ? N6 C14 C15 120.5(3) . . ? O4 C9 C10 115.0(3) . . ? O4 C9 H9A 108.5 . . ? O4 C9 H9B 108.5 . . ? C10 C9 H9A 108.5 . . ? C10 C9 H9B 108.5 . . ? H9A C9 H9B 107.5 . . ? N7 C21 H21 117.9 . . ? N7 C21 C20 124.1(3) . . ? C20 C21 H21 117.9 . . ? C19 C20 H20 120.4 . . ? C21 C20 C19 119.1(3) . . ? C21 C20 H20 120.4 . . ? N7 C17 H17 117.9 . . ? N7 C17 C18 124.1(4) . . ? C18 C17 H17 117.9 . . ? C27 C26 C25 116.0(3) . . ? C27 C26 C23B 141.5(9) . . ? C27 C26 C23A 117.9(4) . . ? C25 C26 C23B 102.4(9) . . ? C25 C26 C23A 126.1(4) . . ? C19 C18 H18 120.1 . . ? C17 C18 C19 119.8(3) . . ? C17 C18 H18 120.1 . . ? C26 C27 H27 119.7 . . ? C28 C27 C26 120.6(4) . . ? C28 C27 H27 119.7 . . ? C24 C25 C26 119.9(4) . . ? C24 C25 H25 120.1 . . ? C26 C25 H25 120.1 . . ? N8 C28 C27 124.1(4) . . ? N8 C28 H28 118.0 . . ? C27 C28 H28 118.0 . . ? C26 C23B H23A 109.8 . . ? C26 C23B H23B 109.8 . . ? H23A C23B H23B 108.2 . . ? C22B C23B C26 110(3) . . ? C22B C23B H23A 109.8 . . ? C22B C23B H23B 109.8 . . ? C19 C22B H22A 109.5 . . ? C19 C22B H22B 109.5 . . ? C23B C22B C19 111(5) . . ? C23B C22B H22A 109.5 . . ? C23B C22B H22B 109.5 . . ? H22A C22B H22B 108.1 . . ? C19 C22A H22C 108.6 . . ? C19 C22A H22D 108.6 . . ? C19 C22A C23A 114.6(9) . . ? H22C C22A H22D 107.6 . . ? C23A C22A H22C 108.6 . . ? C23A C22A H22D 108.6 . . ? C26 C23A C22A 111.3(7) . . ? C26 C23A H23C 109.4 . . ? C26 C23A H23D 109.4 . . ? C22A C23A H23C 109.4 . . ? C22A C23A H23D 109.4 . . ? H23C C23A H23D 108.0 . . ? 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 S1 C2 1.821(3) . ? S1 C3 1.805(3) . ? S2 C10 1.806(3) . ? S2 C11 1.795(3) . ? F1 C7 1.357(3) . ? F2 C15 1.362(3) . ? O5 C12 1.427(3) . ? O5 C10 1.415(3) . ? O2 C2 1.424(3) . ? O2 C4 1.422(3) . ? O6 C13 1.214(4) . ? O3 C5 1.223(4) . ? N4 C12 1.460(3) . ? N4 C16 1.369(4) . ? N4 C13 1.416(3) . ? N1 C8 1.369(4) . ? N1 C5 1.408(3) . ? N1 C4 1.462(3) . ? N2 C5 1.363(3) . ? N2 C6 1.329(4) . ? O4 C9 1.404(5) . ? O4 H4A 0.80(5) . ? O1 C1 1.403(4) . ? O1 H1 0.82(5) . ? N5 C13 1.368(3) . ? N5 C14 1.317(4) . ? N6 C14 1.334(4) . ? N6 H6A 0.91(4) . ? N6 H6B 0.81(5) . ? N8 C24 1.338(5) . ? N8 C28 1.323(5) . ? C8 H8 0.9300 . ? C8 C7 1.332(4) . ? C12 H12 0.9800 . ? C12 C11 1.537(4) . ? N3 C6 1.327(4) . ? N3 H3A 0.87(4) . ? N3 H3B 0.87(4) . ? N7 C21 1.328(5) . ? N7 C17 1.329(5) . ? C16 H16 0.9300 . ? C16 C15 1.323(4) . ? C2 H2 0.9800 . ? C2 C1 1.507(4) . ? C7 C6 1.422(4) . ? C10 H10 0.9800 . ? C10 C9 1.500(5) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C4 H4 0.9800 . ? C4 C3 1.512(4) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C3 H3C 0.9700 . ? C3 H3D 0.9700 . ? C24 H24 0.9300 . ? C24 C25 1.377(5) . ? C15 C14 1.422(4) . ? C19 C20 1.385(5) . ? C19 C18 1.380(5) . ? C19 C22B 1.58(6) . ? C19 C22A 1.503(15) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C21 H21 0.9300 . ? C21 C20 1.378(5) . ? C20 H20 0.9300 . ? C17 H17 0.9300 . ? C17 C18 1.366(5) . ? C26 C27 1.376(5) . ? C26 C25 1.378(5) . ? C26 C23B 1.641(19) . ? C26 C23A 1.513(6) . ? C18 H18 0.9300 . ? C27 H27 0.9300 . ? C27 C28 1.360(5) . ? C25 H25 0.9300 . ? C28 H28 0.9300 . ? C23B H23A 0.9700 . ? C23B H23B 0.9700 . ? C23B C22B 1.30(7) . ? C22B H22A 0.9700 . ? C22B H22B 0.9700 . ? C22A H22C 0.9700 . ? C22A H22D 0.9700 . ? C22A C23A 1.520(15) . ? C23A H23C 0.9700 . ? C23A H23D 0.9700 . ? 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 S1 C2 C1 O1 170.8(2) . . . . ? S2 C10 C9 O4 -47.4(3) . . . . ? F1 C7 C6 N2 175.5(3) . . . . ? F1 C7 C6 N3 -4.7(4) . . . . ? F2 C15 C14 N5 177.9(3) . . . . ? F2 C15 C14 N6 -1.9(4) . . . . ? O5 C12 C11 S2 16.3(3) . . . . ? O5 C10 C9 O4 72.0(4) . . . . ? O2 C2 C1 O1 -69.1(3) . . . . ? O2 C4 C3 S1 -40.6(3) . . . . ? N4 C12 C11 S2 -104.1(2) . . . . ? N4 C16 C15 F2 179.9(3) . . . . ? N4 C16 C15 C14 -0.7(4) . . . . ? N1 C8 C7 F1 -178.1(3) . . . . ? N1 C8 C7 C6 1.9(4) . . . . ? N1 C4 C3 S1 -160.13(19) . . . . ? N8 C24 C25 C26 -0.1(6) . . . . ? C8 N1 C5 O3 175.9(3) . . . . ? C8 N1 C5 N2 -5.1(4) . . . . ? C8 N1 C4 O2 -54.9(3) . . . . ? C8 N1 C4 C3 65.5(3) . . . . ? C8 C7 C6 N2 -4.5(4) . . . . ? C8 C7 C6 N3 175.3(3) . . . . ? C12 O5 C10 S2 -38.2(3) . . . . ? C12 O5 C10 C9 -163.1(3) . . . . ? C12 N4 C16 C15 176.6(3) . . . . ? C12 N4 C13 O6 2.9(4) . . . . ? C12 N4 C13 N5 -177.2(2) . . . . ? N7 C21 C20 C19 1.5(5) . . . . ? N7 C17 C18 C19 0.2(6) . . . . ? C16 N4 C12 O5 -79.4(3) . . . . ? C16 N4 C12 C11 42.3(4) . . . . ? C16 N4 C13 O6 176.4(3) . . . . ? C16 N4 C13 N5 -3.7(4) . . . . ? C16 C15 C14 N5 -1.6(4) . . . . ? C16 C15 C14 N6 178.6(3) . . . . ? C2 S1 C3 C4 36.7(2) . . . . ? C2 O2 C4 N1 147.7(2) . . . . ? C2 O2 C4 C3 23.8(3) . . . . ? C10 S2 C11 C12 -31.7(2) . . . . ? C10 O5 C12 N4 139.1(2) . . . . ? C10 O5 C12 C11 14.3(3) . . . . ? C5 N1 C8 C7 2.9(4) . . . . ? C5 N1 C4 O2 119.9(3) . . . . ? C5 N1 C4 C3 -119.7(3) . . . . ? C5 N2 C6 N3 -177.6(3) . . . . ? C5 N2 C6 C7 2.2(4) . . . . ? C11 S2 C10 O5 40.3(2) . . . . ? C11 S2 C10 C9 162.8(2) . . . . ? C6 N2 C5 O3 -178.6(3) . . . . ? C6 N2 C5 N1 2.4(4) . . . . ? C4 O2 C2 S1 4.8(3) . . . . ? C4 O2 C2 C1 -118.5(3) . . . . ? C4 N1 C8 C7 177.6(3) . . . . ? C4 N1 C5 O3 1.2(4) . . . . ? C4 N1 C5 N2 -179.8(2) . . . . ? C13 N4 C12 O5 94.1(3) . . . . ? C13 N4 C12 C11 -144.2(2) . . . . ? C13 N4 C16 C15 3.3(4) . . . . ? C13 N5 C14 N6 -179.1(3) . . . . ? C13 N5 C14 C15 1.1(4) . . . . ? C3 S1 C2 O2 -25.1(2) . . . . ? C3 S1 C2 C1 96.4(2) . . . . ? C24 N8 C28 C27 0.2(6) . . . . ? C19 C22A C23A C26 175.3(9) . . . . ? C14 N5 C13 O6 -178.6(3) . . . . ? C14 N5 C13 N4 1.5(4) . . . . ? C21 N7 C17 C18 1.2(5) . . . . ? C20 C19 C18 C17 -0.9(5) . . . . ? C20 C19 C22B C23B 90(4) . . . . ? C20 C19 C22A C23A 28.1(19) . . . . ? C17 N7 C21 C20 -2.1(5) . . . . ? C26 C27 C28 N8 0.7(6) . . . . ? C26 C23B C22B C19 -179.0(19) . . . . ? C18 C19 C20 C21 0.1(5) . . . . ? C18 C19 C22B C23B -99(4) . . . . ? C18 C19 C22A C23A -151.7(9) . . . . ? C27 C26 C25 C24 0.9(5) . . . . ? C27 C26 C23B C22B 64(3) . . . . ? C27 C26 C23A C22A 124.7(10) . . . . ? C25 C26 C27 C28 -1.2(6) . . . . ? C25 C26 C23B C22B -117(3) . . . . ? C25 C26 C23A C22A -57.4(11) . . . . ? C28 N8 C24 C25 -0.5(5) . . . . ? C23B C26 C27 C28 178.0(12) . . . . ? C23B C26 C25 C24 -178.6(8) . . . . ? C22B C19 C20 C21 173(3) . . . . ? C22B C19 C18 C17 -171(4) . . . . ? C22A C19 C20 C21 -179.7(10) . . . . ? C22A C19 C18 C17 178.9(10) . . . . ? C23A C26 C27 C28 177.0(4) . . . . ? C23A C26 C25 C24 -177.1(4) . . . . ?