#------------------------------------------------------------------------------ #$Date: 2020-05-07 00:20:09 +0300 (Thu, 07 May 2020) $ #$Revision: 251830 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240472.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_7240472 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 '2(C8 H10 F N3 O3 S), C12 H10 N2' _chemical_formula_sum 'C28 H30 F2 N8 O6 S2' _chemical_formula_weight 676.72 _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)ethylene]' _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 100.406(5) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 7.4883(7) _cell_length_b 11.2957(11) _cell_length_c 18.1735(18) _cell_measurement_reflns_used 7248 _cell_measurement_temperature 298.15 _cell_measurement_theta_max 28.07 _cell_measurement_theta_min 2.906 _cell_volume 1511.9(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 298.15 _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.954 _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 0.0238 _diffrn_reflns_av_unetI/netI 0.0337 _diffrn_reflns_Laue_measured_fraction_full 0.991 _diffrn_reflns_Laue_measured_fraction_max 0.954 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 12872 _diffrn_reflns_point_group_measured_fraction_full 0.881 _diffrn_reflns_point_group_measured_fraction_max 0.814 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.271 _diffrn_reflns_theta_min 2.766 _exptl_absorpt_coefficient_mu 0.246 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_correction_T_min 0.7132 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0625 before and 0.0397 after correction. The Ratio of minimum to maximum transmission is 0.9564. The \l/2 correction factor is Not present.' _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.486 _exptl_crystal_description plate _exptl_crystal_F_000 704 _exptl_crystal_size_max 0.145 _exptl_crystal_size_mid 0.065 _exptl_crystal_size_min 0.03 _refine_diff_density_max 0.261 _refine_diff_density_min -0.190 _refine_diff_density_rms 0.039 _refine_ls_abs_structure_details ; Flack x determined using 1915 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 1.059 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 417 _refine_ls_number_reflns 6094 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.059 _refine_ls_R_factor_all 0.0427 _refine_ls_R_factor_gt 0.0369 _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^)+(0.0342P)^2^+0.4239P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0838 _refine_ls_wR_factor_ref 0.0869 _reflns_Friedel_coverage 0.627 _reflns_Friedel_fraction_full 0.759 _reflns_Friedel_fraction_max 0.660 _reflns_number_gt 5525 _reflns_number_total 6094 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ce00474j2.cif _cod_data_source_block FTC-bpe _cod_database_code 7240472 _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 0.993 _shelx_estimated_absorpt_t_min 0.965 _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.a Ternary CH refined with riding coordinates: C10(H10), C12(H12), C2(H2), C4(H4) 2.b Secondary CH2 refined with riding coordinates: C3(H3C,H3D), C11(H11A,H11B), C1(H1A,H1B), C9(H9A,H9B) 2.c Aromatic/amide H refined with riding coordinates: C8(H8), C16(H16), C18(H18), C24(H24), C27(H27), C20(H20), C17(H17), C25(H25), C22(H22), C28(H28), C23(H23), C21(H21) 2.d X=CH2 refined with riding coordinates: N6(H6A,H6B), N3(H3A,H3B) 2.e Idealised tetrahedral OH refined as rotating group: O1(H1), O4(H4A) ; _shelx_res_file ; TITL mcg19129_a.res in P2(1) mcg19129.res created by SHELXL-2016/6 at 00:46:38 on 06-Oct-2019 REM Old TITL Mcg19_129 in P2(1) sample #19182 Bpe-EMT REM SHELXT solution in P2(1) REM R1 0.127, Rweak 0.044, Alpha 0.005, Orientation as input REM Flack x = 0.066 ( 0.023 ) from Parsons' quotients REM Formula found by SHELXT: C31 F2 N5 O6 S2 CELL 0.71073 7.4883 11.2957 18.1735 90 100.406 90 ZERR 2 0.0007 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 60 4 16 12 4 L.S. 10 PLAN 20 SIZE 0.03 0.065 0.145 TEMP 25 BOND $H CONF HTAB list 4 fmap 2 acta REM REM REM WGHT 0.034200 0.423900 FVAR 0.69172 S1 6 1.044648 0.444830 0.694321 11.00000 0.05275 0.05516 = 0.02449 0.00257 -0.00120 -0.01374 S2 6 0.790098 0.655049 -0.171528 11.00000 0.05123 0.04300 = 0.04134 0.01693 0.00623 -0.00269 F2 3 0.833186 0.816599 0.115762 11.00000 0.10460 0.02733 = 0.04125 -0.00307 0.02122 0.00313 F1 3 0.743781 0.183142 0.367109 11.00000 0.07955 0.03023 = 0.04440 -0.00695 0.00832 -0.00908 O5 5 0.694594 0.490342 -0.089057 11.00000 0.04289 0.04452 = 0.02761 0.00683 0.00435 -0.00863 O3 5 0.998599 0.617768 0.432669 11.00000 0.09387 0.03375 = 0.03131 -0.00041 0.00971 -0.01851 O2 5 0.781966 0.466879 0.577624 11.00000 0.03951 0.06726 = 0.02617 0.00856 0.00741 0.00458 O1 5 0.527267 0.323985 0.647336 11.00000 0.04613 0.07763 = 0.04989 0.01185 0.01167 -0.00631 AFIX 147 H1 2 0.497534 0.329341 0.601768 11.00000 -1.50000 AFIX 0 O6 5 0.933073 0.361070 0.063488 11.00000 0.09387 0.02957 = 0.03780 0.00356 0.00877 0.00914 N1 4 0.917055 0.438449 0.473694 11.00000 0.04436 0.02844 = 0.02260 0.00142 0.00508 -0.00267 N5 4 0.915793 0.506583 0.147580 11.00000 0.05225 0.03495 = 0.02312 0.00323 0.00255 -0.00136 N4 4 0.894692 0.549061 0.017798 11.00000 0.04242 0.02883 = 0.02175 0.00098 0.00473 0.00368 N2 4 0.914671 0.476066 0.345234 11.00000 0.05492 0.03426 = 0.02476 0.00271 0.00522 -0.00256 O4 5 0.385247 0.645592 -0.159156 11.00000 0.04996 0.08788 = 0.04619 0.01986 0.00949 0.02203 AFIX 147 H4A 2 0.395971 0.639108 -0.113628 11.00000 -1.50000 AFIX 0 N6 4 0.894083 0.656126 0.230287 11.00000 0.09272 0.03493 = 0.02550 -0.00324 0.00956 -0.00287 AFIX 93 H6A 2 0.911540 0.606199 0.266605 11.00000 -1.20000 H6B 2 0.878267 0.729849 0.239038 11.00000 -1.20000 AFIX 0 C7 1 0.814740 0.291361 0.385693 11.00000 0.04329 0.02672 = 0.03356 -0.00066 0.00620 -0.00046 N3 4 0.830821 0.330875 0.257468 11.00000 0.08126 0.03843 = 0.02736 -0.00450 0.00951 -0.00722 AFIX 93 H3A 2 0.855131 0.377622 0.223248 11.00000 -1.20000 H3B 2 0.791522 0.260513 0.245996 11.00000 -1.20000 AFIX 0 N8 4 0.386242 0.608913 -0.003499 11.00000 0.04889 0.05565 = 0.04102 0.00440 0.00891 0.00378 C5 1 0.945697 0.516829 0.416670 11.00000 0.04526 0.03037 = 0.02641 0.00434 0.00488 -0.00084 N7 4 0.394199 0.369018 0.492060 11.00000 0.04670 0.06181 = 0.04578 0.00229 0.00513 -0.00041 C8 1 0.849171 0.326789 0.456917 11.00000 0.04493 0.02817 = 0.02913 0.00458 0.00844 -0.00102 AFIX 43 H8 2 0.827419 0.276386 0.494789 11.00000 -1.20000 AFIX 0 C16 1 0.864093 0.666120 0.030804 11.00000 0.04672 0.03049 = 0.02836 0.00713 0.00847 0.00491 AFIX 43 H16 2 0.844355 0.719944 -0.008554 11.00000 -1.20000 AFIX 0 C10 1 0.653713 0.525277 -0.164847 11.00000 0.05010 0.03460 = 0.02386 -0.00148 0.00786 -0.00383 AFIX 13 H10 2 0.692520 0.462439 -0.195651 11.00000 -1.20000 AFIX 0 C13 1 0.915273 0.465755 0.076798 11.00000 0.04341 0.03200 = 0.02830 0.00235 0.00374 0.00206 C6 1 0.854056 0.367482 0.328292 11.00000 0.04295 0.03580 = 0.02422 0.00039 0.00429 0.00454 C12 1 0.883189 0.504103 -0.058366 11.00000 0.04208 0.02964 = 0.02688 0.00068 0.00824 0.00565 AFIX 13 H12 2 0.941424 0.426156 -0.055948 11.00000 -1.20000 AFIX 0 C15 1 0.862989 0.701653 0.100214 11.00000 0.04843 0.02808 = 0.03319 0.00162 0.00902 -0.00193 C2 1 0.802686 0.440508 0.655373 11.00000 0.04681 0.04039 = 0.02478 0.00143 0.00902 0.00260 AFIX 13 H2 2 0.741272 0.502004 0.679567 11.00000 -1.20000 AFIX 0 C3 1 1.094168 0.411524 0.602931 11.00000 0.04021 0.04676 = 0.02865 0.00207 0.00224 -0.00115 AFIX 23 H3C 2 1.214587 0.438628 0.598351 11.00000 -1.20000 H3D 2 1.085046 0.327245 0.592703 11.00000 -1.20000 AFIX 0 C19 1 0.376246 0.424010 0.340637 11.00000 0.04489 0.04973 = 0.04034 0.00184 0.00288 0.00287 C4 1 0.948801 0.479603 0.551181 11.00000 0.04016 0.03366 = 0.02321 0.00077 0.00546 -0.00385 AFIX 13 H4 2 0.982188 0.563561 0.552385 11.00000 -1.20000 AFIX 0 C18 1 0.331295 0.312699 0.363541 11.00000 0.06297 0.04978 = 0.04685 -0.00327 0.00390 -0.00750 AFIX 43 H18 2 0.293490 0.253979 0.328294 11.00000 -1.20000 AFIX 0 C11 1 0.972733 0.584615 -0.109302 11.00000 0.03629 0.04735 = 0.03465 0.00435 0.01129 0.00286 AFIX 23 H11A 2 1.046772 0.538389 -0.137302 11.00000 -1.20000 H11B 2 1.049115 0.643252 -0.079903 11.00000 -1.20000 AFIX 0 C14 1 0.891549 0.619373 0.160678 11.00000 0.03965 0.03851 = 0.02766 0.00008 0.00307 -0.00744 C1 1 0.717660 0.322436 0.666820 11.00000 0.04775 0.04602 = 0.03633 0.00277 0.01057 -0.00290 AFIX 23 H1A 2 0.765232 0.263181 0.636884 11.00000 -1.20000 H1B 2 0.751819 0.299646 0.718926 11.00000 -1.20000 AFIX 0 C26 1 0.403949 0.565195 0.150015 11.00000 0.04279 0.05071 = 0.04205 0.00038 0.00870 0.00476 C24 1 0.404177 0.499719 0.025119 11.00000 0.06516 0.05548 = 0.04638 -0.00771 0.01312 0.00043 AFIX 43 H24 2 0.410711 0.437179 -0.007572 11.00000 -1.20000 AFIX 0 C27 1 0.388770 0.678225 0.120413 11.00000 0.06784 0.04622 = 0.04816 -0.00281 0.01550 0.00813 AFIX 43 H27 2 0.386382 0.742891 0.151895 11.00000 -1.20000 AFIX 0 C20 1 0.426524 0.507963 0.396085 11.00000 0.05144 0.04614 = 0.04352 0.00100 -0.00018 0.00440 AFIX 43 H20 2 0.456639 0.584319 0.383582 11.00000 -1.20000 AFIX 0 C17 1 0.342598 0.289235 0.438156 11.00000 0.05191 0.05702 = 0.05525 0.00707 0.00667 -0.00680 AFIX 43 H17 2 0.312702 0.213579 0.452075 11.00000 -1.20000 AFIX 0 C25 1 0.413613 0.473541 0.099412 11.00000 0.06811 0.04403 = 0.04944 0.00453 0.01420 0.00279 AFIX 43 H25 2 0.426318 0.395531 0.115887 11.00000 -1.20000 AFIX 0 C22 1 0.369758 0.447183 0.260366 11.00000 0.06707 0.05516 = 0.04263 -0.00414 0.00345 -0.00908 AFIX 43 H22 2 0.330390 0.385406 0.227606 11.00000 -1.20000 AFIX 0 C28 1 0.377246 0.695812 0.045350 11.00000 0.05553 0.04903 = 0.05761 0.01023 0.01336 0.00851 AFIX 43 H28 2 0.362256 0.772866 0.027260 11.00000 -1.20000 AFIX 0 C9 1 0.453630 0.543472 -0.188484 11.00000 0.04719 0.07400 = 0.03660 0.00276 -0.00134 -0.00753 AFIX 23 H9A 2 0.425772 0.547651 -0.242659 11.00000 -1.20000 H9B 2 0.391079 0.474993 -0.173275 11.00000 -1.20000 AFIX 0 C23 1 0.413864 0.545991 0.230631 11.00000 0.05769 0.04724 = 0.04630 -0.00213 0.01036 0.00549 AFIX 43 H23 2 0.454288 0.608394 0.262724 11.00000 -1.20000 AFIX 0 C21 1 0.431620 0.477686 0.469722 11.00000 0.05368 0.05810 = 0.04419 -0.00717 0.00020 0.00454 AFIX 43 H21 2 0.462759 0.535880 0.505969 11.00000 -1.20000 AFIX 0 HKLF 4 REM mcg19129_a.res in P2(1) REM R1 = 0.0369 for 5525 Fo > 4sig(Fo) and 0.0427 for all 6094 data REM 417 parameters refined using 1 restraints END WGHT 0.0342 0.4239 REM Instructions for potential hydrogen bonds HTAB O1 N7 HTAB O4 N8 HTAB N6 N2 EQIV $1 -x+2, y+1/2, -z+1 HTAB N6 S1_$1 HTAB N3 N5 EQIV $2 -x+1, y-1/2, -z HTAB N3 O4_$2 EQIV $3 -x+2, y-1/2, -z+1 HTAB C8 O3_$3 HTAB C16 S2 EQIV $4 -x+2, y+1/2, -z HTAB C16 O6_$4 EQIV $5 -x+2, y-1/2, -z HTAB C12 F2_$5 EQIV $6 x+1, y, z HTAB C3 N7_$6 HTAB C3 O3_$3 HTAB C18 S2_$2 HTAB C11 O6_$4 HTAB C11 N8_$6 REM Highest difference peak 0.261, deepest hole -0.190, 1-sigma level 0.039 Q1 1 0.9122 0.4431 0.6887 11.00000 0.05 0.26 Q2 1 1.1865 0.4346 0.6906 11.00000 0.05 0.26 Q3 1 0.5116 0.6581 -0.1695 11.00000 0.05 0.22 Q4 1 0.6498 0.6644 -0.1710 11.00000 0.05 0.20 Q5 1 1.3351 0.4379 0.6906 11.00000 0.05 0.18 Q6 1 0.3890 0.3192 0.6421 11.00000 0.05 0.18 Q7 1 0.5824 0.4742 0.1008 11.00000 0.05 0.15 Q8 1 0.9669 0.8031 0.1151 11.00000 0.05 0.15 Q9 1 0.8114 0.5133 0.1549 11.00000 0.05 0.15 Q10 1 1.0325 0.4521 0.5777 11.00000 0.05 0.15 Q11 1 0.2653 0.6176 0.0008 11.00000 0.05 0.15 Q12 1 1.0269 0.3546 -0.0914 11.00000 0.05 0.14 Q13 1 0.8684 0.6329 0.4332 11.00000 0.05 0.14 Q14 1 0.3448 0.4718 0.0588 11.00000 0.05 0.14 Q15 1 0.7236 0.6441 0.2281 11.00000 0.05 0.14 Q16 1 0.4243 0.6555 0.5580 11.00000 0.05 0.14 Q17 1 0.3872 0.6369 -0.0406 11.00000 0.05 0.14 Q18 1 0.9728 0.4396 0.6398 11.00000 0.05 0.14 Q19 1 0.4335 0.5216 0.2795 11.00000 0.05 0.13 Q20 1 1.0296 0.6746 0.4200 11.00000 0.05 0.13 ; _shelx_res_checksum 31345 _olex2_submission_original_sample_id FTC-bpe _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 1.04465(11) 0.44483(9) 0.69432(4) 0.0451(2) Uani 1 1 d . . . . . S2 S 0.79010(11) 0.65505(8) -0.17153(5) 0.0455(2) Uani 1 1 d . . . . . F2 F 0.8332(3) 0.81660(17) 0.11576(11) 0.0567(6) Uani 1 1 d . . . . . F1 F 0.7438(3) 0.18314(17) 0.36711(11) 0.0518(5) Uani 1 1 d . . . . . O5 O 0.6946(3) 0.4903(2) -0.08906(11) 0.0386(5) Uani 1 1 d . . . . . O3 O 0.9986(4) 0.6178(2) 0.43267(12) 0.0532(6) Uani 1 1 d . . . . . O2 O 0.7820(3) 0.4669(2) 0.57762(10) 0.0441(6) Uani 1 1 d . . . . . O1 O 0.5273(3) 0.3240(3) 0.64734(14) 0.0575(7) Uani 1 1 d . . . . . H1 H 0.497534 0.329341 0.601768 0.086 Uiso 1 1 calc GR . . . . O6 O 0.9331(4) 0.3611(2) 0.06349(13) 0.0541(6) Uani 1 1 d . . . . . N1 N 0.9171(3) 0.4384(2) 0.47369(11) 0.0319(5) Uani 1 1 d . . . . . N5 N 0.9158(3) 0.5066(2) 0.14758(13) 0.0373(6) Uani 1 1 d . . . . . N4 N 0.8947(3) 0.5491(2) 0.01780(12) 0.0311(5) Uani 1 1 d . . . . . N2 N 0.9147(4) 0.4761(2) 0.34523(12) 0.0382(6) Uani 1 1 d . . . . . O4 O 0.3852(3) 0.6456(3) -0.15916(14) 0.0612(7) Uani 1 1 d . . . . . H4A H 0.395971 0.639108 -0.113628 0.092 Uiso 1 1 calc GR . . . . N6 N 0.8941(4) 0.6561(3) 0.23029(14) 0.0512(7) Uani 1 1 d . . . . . H6A H 0.911540 0.606199 0.266605 0.061 Uiso 1 1 calc R . . . . H6B H 0.878267 0.729849 0.239038 0.061 Uiso 1 1 calc R . . . . C7 C 0.8147(4) 0.2914(3) 0.38569(16) 0.0346(6) Uani 1 1 d . . . . . N3 N 0.8308(4) 0.3309(3) 0.25747(14) 0.0491(7) Uani 1 1 d . . . . . H3A H 0.855131 0.377622 0.223248 0.059 Uiso 1 1 calc R . . . . H3B H 0.791522 0.260513 0.245996 0.059 Uiso 1 1 calc R . . . . N8 N 0.3862(4) 0.6089(3) -0.00350(16) 0.0484(7) Uani 1 1 d . . . . . C5 C 0.9457(4) 0.5168(3) 0.41667(15) 0.0342(6) Uani 1 1 d . . . . . N7 N 0.3942(4) 0.3690(3) 0.49206(16) 0.0518(7) Uani 1 1 d . . . . . C8 C 0.8492(4) 0.3268(3) 0.45692(15) 0.0339(6) Uani 1 1 d . . . . . H8 H 0.827419 0.276386 0.494789 0.041 Uiso 1 1 calc R . . . . C16 C 0.8641(4) 0.6661(3) 0.03080(16) 0.0350(6) Uani 1 1 d . . . . . H16 H 0.844355 0.719944 -0.008554 0.042 Uiso 1 1 calc R . . . . C10 C 0.6537(4) 0.5253(3) -0.16485(15) 0.0360(6) Uani 1 1 d . . . . . H10 H 0.692520 0.462439 -0.195651 0.043 Uiso 1 1 calc R . . . . C13 C 0.9153(4) 0.4658(3) 0.07680(15) 0.0349(6) Uani 1 1 d . . . . . C6 C 0.8541(4) 0.3675(3) 0.32829(15) 0.0345(6) Uani 1 1 d . . . . . C12 C 0.8832(4) 0.5041(3) -0.05837(15) 0.0326(6) Uani 1 1 d . . . . . H12 H 0.941424 0.426156 -0.055948 0.039 Uiso 1 1 calc R . . . . C15 C 0.8630(4) 0.7017(3) 0.10021(16) 0.0364(6) Uani 1 1 d . . . . . C2 C 0.8027(4) 0.4405(3) 0.65537(14) 0.0370(6) Uani 1 1 d . . . . . H2 H 0.741272 0.502004 0.679567 0.044 Uiso 1 1 calc R . . . . C3 C 1.0942(4) 0.4115(3) 0.60293(15) 0.0390(7) Uani 1 1 d . . . . . H3C H 1.214587 0.438628 0.598351 0.047 Uiso 1 1 calc R . . . . H3D H 1.085046 0.327245 0.592703 0.047 Uiso 1 1 calc R . . . . C19 C 0.3762(4) 0.4240(3) 0.34064(18) 0.0456(8) Uani 1 1 d . . . . . C4 C 0.9488(4) 0.4796(3) 0.55118(14) 0.0324(6) Uani 1 1 d . . . . . H4 H 0.982188 0.563561 0.552385 0.039 Uiso 1 1 calc R . . . . C18 C 0.3313(5) 0.3127(4) 0.3635(2) 0.0539(9) Uani 1 1 d . . . . . H18 H 0.293490 0.253979 0.328294 0.065 Uiso 1 1 calc R . . . . C11 C 0.9727(4) 0.5846(3) -0.10930(17) 0.0388(7) Uani 1 1 d . . . . . H11A H 1.046772 0.538389 -0.137302 0.047 Uiso 1 1 calc R . . . . H11B H 1.049115 0.643252 -0.079903 0.047 Uiso 1 1 calc R . . . . C14 C 0.8915(4) 0.6194(3) 0.16068(15) 0.0356(6) Uani 1 1 d . . . . . C1 C 0.7177(4) 0.3224(3) 0.66682(18) 0.0430(7) Uani 1 1 d . . . . . H1A H 0.765232 0.263181 0.636884 0.052 Uiso 1 1 calc R . . . . H1B H 0.751819 0.299646 0.718926 0.052 Uiso 1 1 calc R . . . . C26 C 0.4039(4) 0.5652(3) 0.15001(19) 0.0451(8) Uani 1 1 d . . . . . C24 C 0.4042(5) 0.4997(4) 0.0251(2) 0.0553(9) Uani 1 1 d . . . . . H24 H 0.410711 0.437179 -0.007572 0.066 Uiso 1 1 calc R . . . . C27 C 0.3888(5) 0.6782(4) 0.1204(2) 0.0534(9) Uani 1 1 d . . . . . H27 H 0.386382 0.742891 0.151895 0.064 Uiso 1 1 calc R . . . . C20 C 0.4265(5) 0.5080(3) 0.39609(18) 0.0481(8) Uani 1 1 d . . . . . H20 H 0.456639 0.584319 0.383582 0.058 Uiso 1 1 calc R . . . . C17 C 0.3426(5) 0.2892(4) 0.4382(2) 0.0551(9) Uani 1 1 d . . . . . H17 H 0.312702 0.213579 0.452075 0.066 Uiso 1 1 calc R . . . . C25 C 0.4136(5) 0.4735(3) 0.0994(2) 0.0534(9) Uani 1 1 d . . . . . H25 H 0.426318 0.395531 0.115887 0.064 Uiso 1 1 calc R . . . . C22 C 0.3698(5) 0.4472(4) 0.26037(19) 0.0558(9) Uani 1 1 d . . . . . H22 H 0.330390 0.385406 0.227606 0.067 Uiso 1 1 calc R . . . . C28 C 0.3772(5) 0.6958(4) 0.0453(2) 0.0537(9) Uani 1 1 d . . . . . H28 H 0.362256 0.772866 0.027260 0.064 Uiso 1 1 calc R . . . . C9 C 0.4536(5) 0.5435(4) -0.18848(19) 0.0537(9) Uani 1 1 d . . . . . H9A H 0.425772 0.547651 -0.242659 0.064 Uiso 1 1 calc R . . . . H9B H 0.391079 0.474993 -0.173275 0.064 Uiso 1 1 calc R . . . . C23 C 0.4139(5) 0.5460(4) 0.2306(2) 0.0503(8) Uani 1 1 d . . . . . H23 H 0.454288 0.608394 0.262724 0.060 Uiso 1 1 calc R . . . . C21 C 0.4316(5) 0.4777(4) 0.4697(2) 0.0531(9) Uani 1 1 d . . . . . H21 H 0.462759 0.535880 0.505969 0.064 Uiso 1 1 calc R . . . . 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 0.0527(4) 0.0552(5) 0.0245(3) 0.0026(3) -0.0012(3) -0.0137(4) S2 0.0512(4) 0.0430(5) 0.0413(4) 0.0169(4) 0.0062(3) -0.0027(4) F2 0.1046(16) 0.0273(11) 0.0412(10) -0.0031(8) 0.0212(11) 0.0031(11) F1 0.0796(13) 0.0302(11) 0.0444(10) -0.0070(8) 0.0083(9) -0.0091(9) O5 0.0429(11) 0.0445(13) 0.0276(9) 0.0068(9) 0.0043(8) -0.0086(9) O3 0.0939(18) 0.0338(13) 0.0313(11) -0.0004(10) 0.0097(11) -0.0185(13) O2 0.0395(11) 0.0673(17) 0.0262(9) 0.0086(10) 0.0074(8) 0.0046(11) O1 0.0461(13) 0.078(2) 0.0499(14) 0.0119(14) 0.0117(10) -0.0063(13) O6 0.0939(19) 0.0296(13) 0.0378(12) 0.0036(10) 0.0088(12) 0.0091(12) N1 0.0444(12) 0.0284(13) 0.0226(10) 0.0014(10) 0.0051(9) -0.0027(11) N5 0.0522(14) 0.0350(15) 0.0231(11) 0.0032(10) 0.0025(10) -0.0014(12) N4 0.0424(13) 0.0288(14) 0.0217(10) 0.0010(9) 0.0047(9) 0.0037(10) N2 0.0549(15) 0.0343(15) 0.0248(11) 0.0027(10) 0.0052(10) -0.0026(12) O4 0.0500(13) 0.088(2) 0.0462(13) 0.0199(14) 0.0095(11) 0.0220(14) N6 0.093(2) 0.0349(16) 0.0255(12) -0.0032(12) 0.0096(12) -0.0029(16) C7 0.0433(15) 0.0267(15) 0.0336(14) -0.0007(12) 0.0062(12) -0.0005(12) N3 0.081(2) 0.0384(17) 0.0274(13) -0.0045(11) 0.0095(12) -0.0072(15) N8 0.0489(15) 0.056(2) 0.0410(15) 0.0044(14) 0.0089(12) 0.0038(14) C5 0.0453(16) 0.0304(17) 0.0264(13) 0.0043(12) 0.0049(11) -0.0008(13) N7 0.0467(16) 0.062(2) 0.0458(16) 0.0023(15) 0.0051(12) -0.0004(14) C8 0.0449(15) 0.0282(15) 0.0291(13) 0.0046(12) 0.0084(11) -0.0010(13) C16 0.0467(15) 0.0305(16) 0.0284(13) 0.0071(12) 0.0085(11) 0.0049(13) C10 0.0501(16) 0.0346(17) 0.0239(13) -0.0015(12) 0.0079(11) -0.0038(14) C13 0.0434(15) 0.0320(17) 0.0283(13) 0.0023(12) 0.0037(11) 0.0021(13) C6 0.0429(15) 0.0358(17) 0.0242(12) 0.0004(12) 0.0043(11) 0.0045(13) C12 0.0421(15) 0.0296(16) 0.0269(12) 0.0007(11) 0.0082(11) 0.0056(12) C15 0.0484(16) 0.0281(16) 0.0332(15) 0.0016(12) 0.0090(12) -0.0019(13) C2 0.0468(15) 0.0404(18) 0.0248(12) 0.0014(13) 0.0090(11) 0.0026(14) C3 0.0402(15) 0.047(2) 0.0286(13) 0.0021(13) 0.0022(11) -0.0012(14) C19 0.0449(16) 0.050(2) 0.0403(16) 0.0018(15) 0.0029(13) 0.0029(15) C4 0.0402(14) 0.0337(16) 0.0232(12) 0.0008(11) 0.0055(10) -0.0039(12) C18 0.063(2) 0.050(2) 0.047(2) -0.0033(17) 0.0039(16) -0.0075(18) C11 0.0363(14) 0.047(2) 0.0346(14) 0.0043(14) 0.0113(11) 0.0029(13) C14 0.0397(15) 0.0385(18) 0.0277(13) 0.0001(12) 0.0031(11) -0.0074(13) C1 0.0477(17) 0.046(2) 0.0363(16) 0.0028(15) 0.0106(13) -0.0029(15) C26 0.0428(17) 0.051(2) 0.0421(17) 0.0004(15) 0.0087(13) 0.0048(15) C24 0.065(2) 0.055(2) 0.0464(19) -0.0077(18) 0.0131(16) 0.0004(19) C27 0.068(2) 0.046(2) 0.0482(19) -0.0028(17) 0.0155(16) 0.0081(18) C20 0.0514(18) 0.046(2) 0.0435(17) 0.0010(16) -0.0002(14) 0.0044(16) C17 0.052(2) 0.057(2) 0.055(2) 0.0071(19) 0.0067(16) -0.0068(18) C25 0.068(2) 0.044(2) 0.0494(19) 0.0045(17) 0.0142(16) 0.0028(18) C22 0.067(2) 0.055(2) 0.0426(17) -0.0041(18) 0.0034(15) -0.009(2) C28 0.056(2) 0.049(2) 0.058(2) 0.0102(18) 0.0134(16) 0.0085(17) C9 0.0472(18) 0.074(3) 0.0366(17) 0.0028(17) -0.0013(13) -0.0075(18) C23 0.058(2) 0.047(2) 0.0463(18) -0.0021(16) 0.0104(15) 0.0055(16) C21 0.054(2) 0.058(3) 0.0442(18) -0.0072(18) 0.0002(14) 0.0045(18) 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 89.55(13) . . ? C11 S2 C10 88.49(15) . . ? C10 O5 C12 112.0(2) . . ? C4 O2 C2 114.2(2) . . ? C1 O1 H1 109.5 . . ? C5 N1 C4 119.3(2) . . ? C8 N1 C5 120.9(2) . . ? C8 N1 C4 119.7(2) . . ? C14 N5 C13 121.4(3) . . ? C16 N4 C13 120.7(2) . . ? C16 N4 C12 121.0(2) . . ? C13 N4 C12 117.8(2) . . ? C6 N2 C5 121.9(2) . . ? C9 O4 H4A 109.5 . . ? H6A N6 H6B 120.0 . . ? C14 N6 H6A 120.0 . . ? C14 N6 H6B 120.0 . . ? F1 C7 C6 119.2(3) . . ? C8 C7 F1 120.8(3) . . ? C8 C7 C6 120.0(3) . . ? H3A N3 H3B 120.0 . . ? C6 N3 H3A 120.0 . . ? C6 N3 H3B 120.0 . . ? C28 N8 C24 115.7(3) . . ? O3 C5 N1 119.7(3) . . ? O3 C5 N2 122.3(3) . . ? N2 C5 N1 117.9(3) . . ? C17 N7 C21 116.4(3) . . ? N1 C8 H8 120.3 . . ? C7 C8 N1 119.3(3) . . ? C7 C8 H8 120.3 . . ? N4 C16 H16 120.4 . . ? C15 C16 N4 119.1(3) . . ? C15 C16 H16 120.4 . . ? S2 C10 H10 108.7 . . ? O5 C10 S2 105.50(19) . . ? O5 C10 H10 108.7 . . ? O5 C10 C9 110.4(2) . . ? C9 C10 S2 114.8(3) . . ? C9 C10 H10 108.7 . . ? O6 C13 N5 122.2(3) . . ? O6 C13 N4 119.7(3) . . ? N5 C13 N4 118.1(3) . . ? N2 C6 C7 119.8(3) . . ? N2 C6 N3 119.4(3) . . ? N3 C6 C7 120.8(3) . . ? O5 C12 N4 107.0(2) . . ? O5 C12 H12 108.7 . . ? O5 C12 C11 109.7(2) . . ? N4 C12 H12 108.7 . . ? N4 C12 C11 114.0(3) . . ? C11 C12 H12 108.7 . . ? F2 C15 C14 118.1(3) . . ? C16 C15 F2 121.2(3) . . ? C16 C15 C14 120.7(3) . . ? S1 C2 H2 108.7 . . ? O2 C2 S1 107.58(18) . . ? O2 C2 H2 108.7 . . ? O2 C2 C1 110.4(3) . . ? C1 C2 S1 112.6(2) . . ? C1 C2 H2 108.7 . . ? S1 C3 H3C 111.2 . . ? S1 C3 H3D 111.2 . . ? H3C C3 H3D 109.1 . . ? C4 C3 S1 102.8(2) . . ? C4 C3 H3C 111.2 . . ? C4 C3 H3D 111.2 . . ? C18 C19 C20 116.9(3) . . ? C18 C19 C22 119.5(3) . . ? C20 C19 C22 123.7(3) . . ? O2 C4 N1 107.0(2) . . ? O2 C4 C3 108.4(2) . . ? O2 C4 H4 109.0 . . ? N1 C4 C3 114.3(2) . . ? N1 C4 H4 109.0 . . ? C3 C4 H4 109.0 . . ? C19 C18 H18 120.0 . . ? C17 C18 C19 119.9(4) . . ? C17 C18 H18 120.0 . . ? S2 C11 H11A 110.5 . . ? S2 C11 H11B 110.5 . . ? C12 C11 S2 106.0(2) . . ? C12 C11 H11A 110.5 . . ? C12 C11 H11B 110.5 . . ? H11A C11 H11B 108.7 . . ? N5 C14 N6 119.8(3) . . ? N5 C14 C15 119.9(3) . . ? N6 C14 C15 120.3(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 . . ? C27 C26 C25 116.1(3) . . ? C27 C26 C23 120.7(3) . . ? C25 C26 C23 123.2(4) . . ? N8 C24 H24 117.8 . . ? N8 C24 C25 124.5(4) . . ? C25 C24 H24 117.8 . . ? C26 C27 H27 119.7 . . ? C28 C27 C26 120.6(4) . . ? C28 C27 H27 119.7 . . ? C19 C20 H20 120.2 . . ? C21 C20 C19 119.6(4) . . ? C21 C20 H20 120.2 . . ? N7 C17 C18 123.6(4) . . ? N7 C17 H17 118.2 . . ? C18 C17 H17 118.2 . . ? C26 C25 H25 120.4 . . ? C24 C25 C26 119.3(4) . . ? C24 C25 H25 120.4 . . ? C19 C22 H22 116.8 . . ? C23 C22 C19 126.5(4) . . ? C23 C22 H22 116.8 . . ? N8 C28 C27 123.8(4) . . ? N8 C28 H28 118.1 . . ? C27 C28 H28 118.1 . . ? O4 C9 C10 114.7(3) . . ? O4 C9 H9A 108.6 . . ? O4 C9 H9B 108.6 . . ? C10 C9 H9A 108.6 . . ? C10 C9 H9B 108.6 . . ? H9A C9 H9B 107.6 . . ? C26 C23 H23 117.7 . . ? C22 C23 C26 124.5(4) . . ? C22 C23 H23 117.7 . . ? N7 C21 C20 123.6(4) . . ? N7 C21 H21 118.2 . . ? C20 C21 H21 118.2 . . ? 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 S1 C2 1.823(3) . ? S1 C3 1.806(3) . ? S2 C10 1.803(3) . ? S2 C11 1.795(3) . ? F2 C15 1.356(4) . ? F1 C7 1.351(4) . ? O5 C10 1.412(3) . ? O5 C12 1.430(3) . ? O3 C5 1.225(4) . ? O2 C2 1.425(3) . ? O2 C4 1.425(3) . ? O1 H1 0.8200 . ? O1 C1 1.406(4) . ? O6 C13 1.219(4) . ? N1 C5 1.409(4) . ? N1 C8 1.373(4) . ? N1 C4 1.461(3) . ? N5 C13 1.366(4) . ? N5 C14 1.315(4) . ? N4 C16 1.370(4) . ? N4 C13 1.414(4) . ? N4 C12 1.462(3) . ? N2 C5 1.357(4) . ? N2 C6 1.325(4) . ? O4 H4A 0.8200 . ? O4 C9 1.406(5) . ? N6 H6A 0.8600 . ? N6 H6B 0.8600 . ? N6 C14 1.328(4) . ? C7 C8 1.335(4) . ? C7 C6 1.423(4) . ? N3 H3A 0.8600 . ? N3 H3B 0.8600 . ? N3 C6 1.333(4) . ? N8 C24 1.336(5) . ? N8 C28 1.333(5) . ? N7 C17 1.336(5) . ? N7 C21 1.338(5) . ? C8 H8 0.9300 . ? C16 H16 0.9300 . ? C16 C15 1.325(4) . ? C10 H10 0.9800 . ? C10 C9 1.496(5) . ? C12 H12 0.9800 . ? C12 C11 1.536(4) . ? C15 C14 1.426(4) . ? C2 H2 0.9800 . ? C2 C1 1.508(5) . ? C3 H3C 0.9700 . ? C3 H3D 0.9700 . ? C3 C4 1.514(4) . ? C19 C18 1.385(5) . ? C19 C20 1.385(5) . ? C19 C22 1.474(5) . ? C4 H4 0.9800 . ? C18 H18 0.9300 . ? C18 C17 1.369(5) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C26 C27 1.382(5) . ? C26 C25 1.395(5) . ? C26 C23 1.470(5) . ? C24 H24 0.9300 . ? C24 C25 1.371(5) . ? C27 H27 0.9300 . ? C27 C28 1.366(5) . ? C20 H20 0.9300 . ? C20 C21 1.375(5) . ? C17 H17 0.9300 . ? C25 H25 0.9300 . ? C22 H22 0.9300 . ? C22 C23 1.308(5) . ? C28 H28 0.9300 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C23 H23 0.9300 . ? C21 H21 0.9300 . ? 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 170.9(2) . . . . ? S1 C3 C4 O2 -41.1(3) . . . . ? S1 C3 C4 N1 -160.3(2) . . . . ? S2 C10 C9 O4 -46.5(3) . . . . ? F2 C15 C14 N5 178.1(3) . . . . ? F2 C15 C14 N6 -2.0(4) . . . . ? F1 C7 C8 N1 -178.4(3) . . . . ? F1 C7 C6 N2 176.5(3) . . . . ? F1 C7 C6 N3 -3.6(4) . . . . ? O5 C10 C9 O4 72.5(4) . . . . ? O5 C12 C11 S2 14.3(3) . . . . ? O2 C2 C1 O1 -68.9(3) . . . . ? N4 C16 C15 F2 -180.0(3) . . . . ? N4 C16 C15 C14 -0.6(4) . . . . ? N4 C12 C11 S2 -105.7(2) . . . . ? N8 C24 C25 C26 0.1(6) . . . . ? C5 N1 C8 C7 1.8(4) . . . . ? C5 N1 C4 O2 120.8(3) . . . . ? C5 N1 C4 C3 -119.2(3) . . . . ? C5 N2 C6 C7 1.8(4) . . . . ? C5 N2 C6 N3 -178.1(3) . . . . ? C8 N1 C5 O3 176.7(3) . . . . ? C8 N1 C5 N2 -3.9(4) . . . . ? C8 N1 C4 O2 -55.1(3) . . . . ? C8 N1 C4 C3 64.9(3) . . . . ? C8 C7 C6 N2 -4.0(4) . . . . ? C8 C7 C6 N3 175.9(3) . . . . ? C16 N4 C13 O6 176.2(3) . . . . ? C16 N4 C13 N5 -4.3(4) . . . . ? C16 N4 C12 O5 -78.6(3) . . . . ? C16 N4 C12 C11 42.9(4) . . . . ? C16 C15 C14 N5 -1.3(4) . . . . ? C16 C15 C14 N6 178.6(3) . . . . ? C10 S2 C11 C12 -30.3(2) . . . . ? C10 O5 C12 N4 140.3(2) . . . . ? C10 O5 C12 C11 16.1(3) . . . . ? C13 N5 C14 N6 -179.5(3) . . . . ? C13 N5 C14 C15 0.3(4) . . . . ? C13 N4 C16 C15 3.4(4) . . . . ? C13 N4 C12 O5 93.5(3) . . . . ? C13 N4 C12 C11 -145.0(3) . . . . ? C6 N2 C5 O3 -178.7(3) . . . . ? C6 N2 C5 N1 2.0(4) . . . . ? C6 C7 C8 N1 2.1(4) . . . . ? C12 O5 C10 S2 -39.1(3) . . . . ? C12 O5 C10 C9 -163.6(3) . . . . ? C12 N4 C16 C15 175.2(3) . . . . ? C12 N4 C13 O6 4.1(4) . . . . ? C12 N4 C13 N5 -176.4(2) . . . . ? C2 S1 C3 C4 37.0(2) . . . . ? C2 O2 C4 N1 147.9(3) . . . . ? C2 O2 C4 C3 24.2(4) . . . . ? C3 S1 C2 O2 -25.2(2) . . . . ? C3 S1 C2 C1 96.7(2) . . . . ? C19 C18 C17 N7 0.6(6) . . . . ? C19 C20 C21 N7 1.6(5) . . . . ? C19 C22 C23 C26 -179.6(3) . . . . ? C4 O2 C2 S1 4.6(3) . . . . ? C4 O2 C2 C1 -118.7(3) . . . . ? C4 N1 C5 O3 0.8(4) . . . . ? C4 N1 C5 N2 -179.9(2) . . . . ? C4 N1 C8 C7 177.7(3) . . . . ? C18 C19 C20 C21 0.7(5) . . . . ? C18 C19 C22 C23 -177.6(4) . . . . ? C11 S2 C10 O5 40.1(2) . . . . ? C11 S2 C10 C9 161.7(2) . . . . ? C14 N5 C13 O6 -178.1(3) . . . . ? C14 N5 C13 N4 2.4(4) . . . . ? C26 C27 C28 N8 -2.5(6) . . . . ? C24 N8 C28 C27 1.3(5) . . . . ? C27 C26 C25 C24 -1.2(5) . . . . ? C27 C26 C23 C22 156.7(4) . . . . ? C20 C19 C18 C17 -1.7(5) . . . . ? C20 C19 C22 C23 2.0(6) . . . . ? C17 N7 C21 C20 -2.7(5) . . . . ? C25 C26 C27 C28 2.4(5) . . . . ? C25 C26 C23 C22 -25.0(6) . . . . ? C22 C19 C18 C17 177.9(3) . . . . ? C22 C19 C20 C21 -178.9(3) . . . . ? C28 N8 C24 C25 -0.1(5) . . . . ? C23 C26 C27 C28 -179.2(3) . . . . ? C23 C26 C25 C24 -179.6(3) . . . . ? C21 N7 C17 C18 1.7(5) . . . . ?