#------------------------------------------------------------------------------ #$Date: 2020-02-11 04:11:45 +0200 (Tue, 11 Feb 2020) $ #$Revision: 248019 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/72/1557293.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_1557293 loop_ _publ_author_name 'Schnell, Simon D.' 'Hoff, Lukas V.' 'Panchagnula, Advaita' 'Wurzenberger, Maximilian Hans Horst' 'Klapoetke, Thomas M.' 'Sieber, Simon' 'Linden, Anthony' 'Gademann, Karl' _publ_section_title ; 3-Bromotetrazine: Labelling of Macromolecules via Monosubstituted Bifunctional s-Tetrazines ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/C9SC06169J _journal_year 2020 _chemical_formula_moiety 'C9 H9 N7 O2 S2' _chemical_formula_sum 'C9 H9 N7 O2 S2' _chemical_formula_weight 311.35 _chemical_melting_point 419 _chemical_name_systematic N-(2-((3-nitropyridin-2-yl)disulfaneyl)ethyl)-1,2,4,5-tetrazin-3-amine _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2019-10-11 deposited with the CCDC. 2020-02-10 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 93.9389(13) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 17.7417(3) _cell_length_b 6.22991(9) _cell_length_c 23.2377(3) _cell_measurement_reflns_used 10728 _cell_measurement_temperature 160(2) _cell_measurement_theta_max 30.1500 _cell_measurement_theta_min 3.4450 _cell_volume 2562.38(7) _computing_cell_refinement 'CrysAlisPro, Version 1.171.40.53 (Rigaku Oxford Diffraction, 2019)' _computing_data_collection 'CrysAlisPro, Version 1.171.40.53 (Rigaku Oxford Diffraction, 2019)' _computing_data_reduction 'CrysAlisPro, Version 1.171.40.53 (Rigaku Oxford Diffraction, 2019)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL-2018 and PLATON (Spek, 2015)' _computing_structure_refinement 'SHELXL-2018 (Sheldrick, 2015b)' _computing_structure_solution 'SHELXT-2018 (Sheldrick, 2015a)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 160(2) _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 10.3801 _diffrn_detector_type 'Atlas CCD area detector on \k goniostat' _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.932 _diffrn_measurement_device 'four-circle \k-geometry diffractometer' _diffrn_measurement_device_type 'Oxford Diffraction SuperNova, dual radiation diffractometer' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0187 _diffrn_reflns_av_unetI/netI 0.0156 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.932 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_number 16497 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.932 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 30.243 _diffrn_reflns_theta_min 2.798 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Mo) X-ray source' _exptl_absorpt_coefficient_mu 0.429 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.92715 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Empirical absorption correction using spherical harmonics, implemented in the SCALE3 ABSPACK scaling algorithm. CrysAlisPro, Version 1.171.40.53 (Rigaku Oxford Diffraction, 2019) ; _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.614 _exptl_crystal_description prism _exptl_crystal_F_000 1280 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: dichloromethane / acetonitrile' _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.318 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.043 _refine_ls_extinction_coef 0.00065(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018 (Sheldrick, 2015b)' _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 186 _refine_ls_number_reflns 3564 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.060 _refine_ls_R_factor_all 0.0309 _refine_ls_R_factor_gt 0.0266 _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^)+(0.0311P)^2^+1.7110P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0674 _refine_ls_wR_factor_ref 0.0704 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3204 _reflns_number_total 3564 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9sc06169j2.cif _cod_data_source_block 39 _cod_depositor_comments ; The following automatic conversions were performed: data item '_atom_sites_solution_hydrogens' value 'geom & difmap' was changed to 'mixed'. Automatic conversion script Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas ; _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 1557293 _shelx_shelxl_version_number 2018/3 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _oxdiff_exptl_absorpt_empirical_full_min 0.857 _oxdiff_exptl_absorpt_empirical_full_max 1.161 _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _shelx_res_file ; TITL gd1907_mo_a.res in C2/c x.res created by SHELXL-2018/3 at 17:14:49 on 11-Sep-2019 REM Old TITL GD1907_Mo in C2/c REM SHELXT solution in C2/c: R1 0.135, Rweak 0.096, Alpha 0.019 REM 0.838 for 250 systematic absences, Orientation as input REM Formula found by SHELXT: C2 N7 O1 S2 CELL 0.71073 17.7417 6.22991 23.2377 90 93.9389 90 ZERR 8 0.0003 0.00009 0.0003 0 0.0013 0 LATT 7 SYMM -X,+Y,0.5-Z SFAC C H N O S UNIT 72 72 56 16 16 L.S. 4 PLAN 10 TEMP -113 BOND $H CONF EQIV $1 x, y+1, z HTAB N5 N3_$1 fmap 2 acta WGHT 0.031100 1.711000 EXTI 0.000654 FVAR 2.67902 S1 5 0.642072 0.545737 0.383241 11.00000 0.01912 0.02601 = 0.02840 -0.00407 -0.00378 -0.00020 S2 5 0.730119 0.753034 0.377435 11.00000 0.02540 0.01837 = 0.03034 -0.00132 -0.00691 -0.00136 O1 4 0.838562 1.042840 0.380842 11.00000 0.03543 0.03086 = 0.04683 0.00287 -0.00238 -0.00640 O2 4 0.939276 1.076129 0.437585 11.00000 0.05108 0.06108 = 0.04709 -0.00145 -0.00843 -0.03670 N1 3 0.542219 0.225705 0.179473 11.00000 0.03541 0.03767 = 0.02647 -0.00034 -0.00498 0.00660 N2 3 0.508493 0.057690 0.155264 11.00000 0.02788 0.05391 = 0.02916 -0.01025 -0.00584 0.00272 N3 3 0.583689 -0.177507 0.215080 11.00000 0.03610 0.02582 = 0.03310 -0.00713 0.00128 -0.00478 N4 3 0.618544 -0.012490 0.240720 11.00000 0.02936 0.02357 = 0.02654 -0.00318 -0.00304 -0.00137 N5 3 0.632169 0.355024 0.246741 11.00000 0.04448 0.02168 = 0.02395 -0.00053 -0.00158 -0.00398 H5 2 0.615776 0.479369 0.236340 11.00000 0.03976 N6 3 0.781947 0.484802 0.460995 11.00000 0.02490 0.02886 = 0.02344 -0.00131 -0.00471 -0.00284 N7 3 0.882076 0.978897 0.420686 11.00000 0.03016 0.03286 = 0.03177 -0.00951 0.00229 -0.01081 C1 1 0.597223 0.185542 0.222139 11.00000 0.02587 0.02574 = 0.01853 -0.00201 0.00195 0.00043 C2 1 0.530147 -0.137084 0.173764 11.00000 0.03363 0.04163 = 0.03912 -0.01581 -0.00507 -0.00743 AFIX 43 H2 2 0.505120 -0.256917 0.155843 11.00000 -1.20000 AFIX 0 C3 1 0.696565 0.332005 0.288492 11.00000 0.02773 0.03374 = 0.03374 -0.01186 0.00313 -0.00921 AFIX 23 H31 2 0.729068 0.460549 0.286390 11.00000 -1.20000 H32 2 0.726594 0.206125 0.277699 11.00000 -1.20000 AFIX 0 C4 1 0.675658 0.304399 0.349869 11.00000 0.02540 0.01864 = 0.02952 -0.00190 -0.00775 -0.00114 AFIX 23 H41 2 0.720483 0.251086 0.373316 11.00000 -1.20000 H42 2 0.635917 0.193078 0.350620 11.00000 -1.20000 AFIX 0 C5 1 0.797055 0.666548 0.433662 11.00000 0.02078 0.02400 = 0.02169 -0.00701 -0.00108 -0.00052 C6 1 0.831451 0.412972 0.502868 11.00000 0.03051 0.03733 = 0.02308 0.00116 -0.00431 -0.00102 AFIX 43 H6 2 0.819904 0.283567 0.522020 11.00000 -1.20000 AFIX 0 C7 1 0.898452 0.516697 0.519780 11.00000 0.02661 0.04752 = 0.02443 -0.00348 -0.00618 0.00147 AFIX 43 H7 2 0.931986 0.459853 0.549586 11.00000 -1.20000 AFIX 0 C8 1 0.914895 0.703819 0.492206 11.00000 0.02163 0.04394 = 0.02667 -0.01107 -0.00264 -0.00546 AFIX 43 H8 2 0.960053 0.780488 0.502681 11.00000 -1.20000 AFIX 0 C9 1 0.864233 0.778792 0.448715 11.00000 0.02314 0.02886 = 0.02386 -0.00930 0.00169 -0.00364 HKLF 4 REM gd1907_mo_a.res in C2/c REM wR2 = 0.0704, GooF = S = 1.060, Restrained GooF = 1.060 for all data REM R1 = 0.0266 for 3204 Fo > 4sig(Fo) and 0.0309 for all 3564 data REM 186 parameters refined using 0 restraints END WGHT 0.0311 1.7110 REM Highest difference peak 0.318, deepest hole -0.215, 1-sigma level 0.043 Q1 1 0.6820 0.3049 0.3196 11.00000 0.05 0.32 Q2 1 0.8313 0.7300 0.4378 11.00000 0.05 0.29 Q3 1 0.9616 0.9825 0.4311 11.00000 0.05 0.28 Q4 1 0.5515 -0.1353 0.2006 11.00000 0.05 0.25 Q5 1 0.7700 0.6973 0.4064 11.00000 0.05 0.24 Q6 1 0.8704 0.4562 0.5039 11.00000 0.05 0.24 Q7 1 0.8984 0.7137 0.4618 11.00000 0.05 0.24 Q8 1 0.5731 0.1991 0.2026 11.00000 0.05 0.24 Q9 1 0.8066 0.4604 0.4806 11.00000 0.05 0.22 Q10 1 0.8816 0.7704 0.4765 11.00000 0.05 0.22 ; _shelx_res_checksum 67775 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp S1 S 0.64207(2) 0.54574(5) 0.38324(2) 0.02476(8) Uani 1 1 d . . S2 S 0.73012(2) 0.75303(4) 0.37744(2) 0.02511(8) Uani 1 1 d . . O1 O 0.83856(5) 1.04284(15) 0.38084(4) 0.0379(2) Uani 1 1 d . . O2 O 0.93928(6) 1.0761(2) 0.43758(5) 0.0536(3) Uani 1 1 d . . N1 N 0.54222(6) 0.22570(18) 0.17947(4) 0.0335(2) Uani 1 1 d . . N2 N 0.50849(6) 0.0577(2) 0.15526(5) 0.0373(3) Uani 1 1 d . . N3 N 0.58369(6) -0.17751(17) 0.21508(5) 0.0317(2) Uani 1 1 d . . N4 N 0.61854(6) -0.01249(16) 0.24072(4) 0.0267(2) Uani 1 1 d . . N5 N 0.63217(7) 0.35502(17) 0.24674(4) 0.0302(2) Uani 1 1 d . . H5 H 0.6158(9) 0.479(3) 0.2363(7) 0.040(4) Uiso 1 1 d . . N6 N 0.78195(5) 0.48480(16) 0.46100(4) 0.0260(2) Uani 1 1 d . . N7 N 0.88208(6) 0.97890(18) 0.42069(5) 0.0316(2) Uani 1 1 d . . C1 C 0.59722(6) 0.18554(19) 0.22214(4) 0.0234(2) Uani 1 1 d . . C2 C 0.53015(8) -0.1371(2) 0.17376(6) 0.0385(3) Uani 1 1 d . . H2 H 0.505120 -0.256917 0.155843 0.046 Uiso 1 1 calc R U C3 C 0.69657(7) 0.3320(2) 0.28849(5) 0.0317(3) Uani 1 1 d . . H31 H 0.729068 0.460549 0.286390 0.038 Uiso 1 1 calc R U H32 H 0.726594 0.206125 0.277699 0.038 Uiso 1 1 calc R U C4 C 0.67566(6) 0.30440(18) 0.34987(5) 0.0250(2) Uani 1 1 d . . H41 H 0.720483 0.251086 0.373316 0.030 Uiso 1 1 calc R U H42 H 0.635917 0.193078 0.350620 0.030 Uiso 1 1 calc R U C5 C 0.79705(6) 0.66655(18) 0.43366(4) 0.0223(2) Uani 1 1 d . . C6 C 0.83145(7) 0.4130(2) 0.50287(5) 0.0306(3) Uani 1 1 d . . H6 H 0.819904 0.283567 0.522020 0.037 Uiso 1 1 calc R U C7 C 0.89845(7) 0.5167(2) 0.51978(5) 0.0332(3) Uani 1 1 d . . H7 H 0.931986 0.459853 0.549586 0.040 Uiso 1 1 calc R U C8 C 0.91489(7) 0.7038(2) 0.49221(5) 0.0309(3) Uani 1 1 d . . H8 H 0.960053 0.780488 0.502681 0.037 Uiso 1 1 calc R U C9 C 0.86423(6) 0.77879(19) 0.44872(5) 0.0253(2) Uani 1 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.01912(13) 0.02601(15) 0.02840(14) -0.00407(10) -0.00378(10) -0.00020(10) S2 0.02540(14) 0.01837(14) 0.03034(15) -0.00132(10) -0.00691(10) -0.00136(10) O1 0.0354(5) 0.0309(5) 0.0468(5) 0.0029(4) -0.0024(4) -0.0064(4) O2 0.0511(6) 0.0611(7) 0.0471(6) -0.0015(5) -0.0084(5) -0.0367(6) N1 0.0354(6) 0.0377(6) 0.0265(5) -0.0003(4) -0.0050(4) 0.0066(5) N2 0.0279(5) 0.0539(7) 0.0292(5) -0.0102(5) -0.0058(4) 0.0027(5) N3 0.0361(5) 0.0258(5) 0.0331(5) -0.0071(4) 0.0013(4) -0.0048(4) N4 0.0294(5) 0.0236(5) 0.0265(5) -0.0032(4) -0.0030(4) -0.0014(4) N5 0.0445(6) 0.0217(5) 0.0240(5) -0.0005(4) -0.0016(4) -0.0040(4) N6 0.0249(5) 0.0289(5) 0.0234(4) -0.0013(4) -0.0047(4) -0.0028(4) N7 0.0302(5) 0.0329(5) 0.0318(5) -0.0095(4) 0.0023(4) -0.0108(4) C1 0.0259(5) 0.0257(5) 0.0185(5) -0.0020(4) 0.0019(4) 0.0004(4) C2 0.0336(6) 0.0416(7) 0.0391(7) -0.0158(6) -0.0051(5) -0.0074(6) C3 0.0277(6) 0.0337(6) 0.0337(6) -0.0119(5) 0.0031(5) -0.0092(5) C4 0.0254(5) 0.0186(5) 0.0295(5) -0.0019(4) -0.0077(4) -0.0011(4) C5 0.0208(5) 0.0240(5) 0.0217(5) -0.0070(4) -0.0011(4) -0.0005(4) C6 0.0305(6) 0.0373(6) 0.0231(5) 0.0012(5) -0.0043(4) -0.0010(5) C7 0.0266(6) 0.0475(7) 0.0244(5) -0.0035(5) -0.0062(4) 0.0015(5) C8 0.0216(5) 0.0439(7) 0.0267(5) -0.0111(5) -0.0026(4) -0.0055(5) C9 0.0231(5) 0.0289(6) 0.0239(5) -0.0093(4) 0.0017(4) -0.0036(4) 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' 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 C4 S1 S2 102.79(4) C5 S2 S1 103.55(4) N2 N1 C1 116.54(11) N1 N2 C2 118.30(10) N4 N3 C2 117.92(11) N3 N4 C1 117.01(10) C1 N5 C3 121.93(11) C1 N5 H5 117.2(11) C3 N5 H5 120.9(11) C5 N6 C6 119.03(10) O2 N7 O1 123.03(12) O2 N7 C9 118.88(11) O1 N7 C9 118.09(10) N5 C1 N4 118.29(10) N5 C1 N1 117.02(11) N4 C1 N1 124.69(10) N3 C2 N2 125.53(12) N3 C2 H2 117.2 N2 C2 H2 117.2 N5 C3 C4 114.16(10) N5 C3 H31 108.7 C4 C3 H31 108.7 N5 C3 H32 108.7 C4 C3 H32 108.7 H31 C3 H32 107.6 C3 C4 S1 114.82(8) C3 C4 H41 108.6 S1 C4 H41 108.6 C3 C4 H42 108.6 S1 C4 H42 108.6 H41 C4 H42 107.5 N6 C5 C9 119.90(10) N6 C5 S2 117.30(8) C9 C5 S2 122.79(9) N6 C6 C7 123.78(12) N6 C6 H6 118.1 C7 C6 H6 118.1 C8 C7 C6 118.02(11) C8 C7 H7 121.0 C6 C7 H7 121.0 C7 C8 C9 118.61(11) C7 C8 H8 120.7 C9 C8 H8 120.7 C8 C9 C5 120.67(11) C8 C9 N7 117.77(10) C5 C9 N7 121.54(10) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 C4 1.8112(12) S1 S2 2.0384(4) S2 C5 1.7873(11) O1 N7 1.2303(14) O2 N7 1.2232(14) N1 N2 1.3130(16) N1 C1 1.3656(14) N2 C2 1.3350(19) N3 N4 1.3205(14) N3 C2 1.3275(17) N4 C1 1.3525(15) N5 C1 1.3332(15) N5 C3 1.4543(16) N5 H5 0.856(17) N6 C5 1.3344(15) N6 C6 1.3420(15) N7 C9 1.4515(16) C2 H2 0.9500 C3 C4 1.5080(17) C3 H31 0.9900 C3 H32 0.9900 C4 H41 0.9900 C4 H42 0.9900 C5 C9 1.4052(15) C6 C7 1.3860(17) C6 H6 0.9500 C7 C8 1.3712(19) C7 H7 0.9500 C8 C9 1.3866(17) C8 H8 0.9500 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag N5 H5 N3 0.856(17) 2.258(17) 3.1106(16) 173.5(15) 1_565 yes 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 C1 N1 N2 C2 -0.09(17) C2 N3 N4 C1 -0.75(16) C3 N5 C1 N4 5.97(17) C3 N5 C1 N1 -173.78(10) N3 N4 C1 N5 -179.13(11) N3 N4 C1 N1 0.61(17) N2 N1 C1 N5 179.57(11) N2 N1 C1 N4 -0.17(17) N4 N3 C2 N2 0.6(2) N1 N2 C2 N3 -0.1(2) C1 N5 C3 C4 -87.15(14) N5 C3 C4 S1 -73.55(12) S2 S1 C4 C3 -58.14(8) C6 N6 C5 C9 0.36(16) C6 N6 C5 S2 178.99(9) S1 S2 C5 N6 7.52(9) S1 S2 C5 C9 -173.90(8) C5 N6 C6 C7 -0.15(18) N6 C6 C7 C8 0.2(2) C6 C7 C8 C9 -0.47(18) C7 C8 C9 C5 0.69(17) C7 C8 C9 N7 179.04(11) N6 C5 C9 C8 -0.64(17) S2 C5 C9 C8 -179.19(9) N6 C5 C9 N7 -178.93(10) S2 C5 C9 N7 2.53(15) O2 N7 C9 C8 -2.30(17) O1 N7 C9 C8 177.75(11) O2 N7 C9 C5 176.03(12) O1 N7 C9 C5 -3.91(16)