#------------------------------------------------------------------------------ #$Date: 2019-11-17 07:44:38 +0200 (Sun, 17 Nov 2019) $ #$Revision: 228722 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/54/78/1547871.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_1547871 loop_ _publ_author_name 'Wei, Peng' 'Yuan, Wei' 'Xue, Fengfeng' 'Zhou, Wei' 'Li, Ruohan' 'Zhang, Datong' 'Yi, Tao' _publ_section_title ; Deformylation reaction-based probe for in vivo imaging of HOCl. ; _journal_issue 2 _journal_name_full 'Chemical science' _journal_page_first 495 _journal_page_last 501 _journal_paper_doi 10.1039/c7sc03784h _journal_volume 9 _journal_year 2018 _chemical_formula_sum 'C19 H24 N4 O S' _chemical_formula_weight 356.48 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2017-06-13 deposited with the CCDC. 2017-11-02 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 94.096(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 5.9414(11) _cell_length_b 15.879(3) _cell_length_c 19.207(4) _cell_measurement_reflns_used 2271 _cell_measurement_temperature 223(2) _cell_measurement_theta_max 24.05 _cell_measurement_theta_min 2.48 _cell_volume 1807.4(6) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 223(2) _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0532 _diffrn_reflns_av_unetI/netI 0.0609 _diffrn_reflns_Laue_measured_fraction_full 0.995 _diffrn_reflns_Laue_measured_fraction_max 0.994 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 13232 _diffrn_reflns_point_group_measured_fraction_full 0.995 _diffrn_reflns_point_group_measured_fraction_max 0.994 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.613 _diffrn_reflns_theta_min 1.666 _exptl_absorpt_coefficient_mu 0.194 _exptl_absorpt_correction_T_max 0.956 _exptl_absorpt_correction_T_min 0.860 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.310 _exptl_crystal_description sheet _exptl_crystal_F_000 760 _exptl_crystal_size_max 0.380 _exptl_crystal_size_mid 0.280 _exptl_crystal_size_min 0.080 _refine_diff_density_max 0.257 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.051 _refine_ls_extinction_coef 0.0098(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2014/7 (Sheldrick 2014' _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 233 _refine_ls_number_reflns 4176 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.010 _refine_ls_R_factor_all 0.0791 _refine_ls_R_factor_gt 0.0461 _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^)+(0.0376P)^2^+0.8497P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0991 _refine_ls_wR_factor_ref 0.1139 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2870 _reflns_number_total 4176 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7sc03784h5.cif _cod_data_source_block mo_70223a _cod_depositor_comments 'Adding full bibliography for 1547871--1547872.cif.' _cod_database_code 1547871 _shelx_shelxl_version_number 2014/7 _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_min 0.930 _shelx_estimated_absorpt_t_max 0.985 _shelx_res_file ; mo_70223a.res created by SHELXL-2014/7 TITL mo_70223a in P2(1)/n CELL 0.71073 5.9414 15.8790 19.2066 90.000 94.096 90.000 ZERR 4.00 0.0011 0.0030 0.0035 0.000 0.003 0.000 LATT 1 SYMM 0.5-X, 0.5+Y, 0.5-Z SFAC C H N O S UNIT 76 96 16 4 4 L.S. 5 ACTA BOND FMAP 2 PLAN 1 SIZE 0.08 0.28 0.38 CONF TEMP -50 WGHT 0.037600 0.849700 EXTI 0.009780 FVAR 0.21977 MOLE 1 S1 5 -0.309273 0.820915 0.163049 11.00000 0.02526 0.04775 = 0.02313 -0.00153 0.00361 0.00459 N1 3 0.106880 0.719289 0.155742 11.00000 0.03613 0.02735 = 0.02204 -0.00197 0.00592 0.00649 N2 3 0.110845 0.581229 0.198422 11.00000 0.04147 0.02567 = 0.03405 -0.00203 0.01209 0.00323 N3 3 -0.009761 0.856575 0.421505 11.00000 0.03529 0.03879 = 0.02135 -0.00495 0.00318 0.00456 N4 3 -0.110333 0.924787 -0.078973 11.00000 0.04496 0.06085 = 0.03165 0.01617 0.01202 0.01552 O1 4 0.290599 0.612920 0.102308 11.00000 0.07864 0.03987 = 0.04299 0.00025 0.03170 0.02077 C1 1 -0.104645 0.805225 0.233472 11.00000 0.02592 0.02805 = 0.02221 -0.00042 0.00203 -0.00071 C2 1 0.084820 0.757051 0.222436 11.00000 0.02981 0.02509 = 0.02188 -0.00323 0.00541 0.00067 C3 1 0.248369 0.747259 0.277013 11.00000 0.03085 0.02597 = 0.02875 0.00050 0.00489 0.00593 AFIX 43 H3 2 0.382186 0.718193 0.269339 11.00000 -1.20000 AFIX 0 C4 1 0.218075 0.779425 0.342345 11.00000 0.03083 0.02879 = 0.02442 0.00138 0.00015 0.00225 AFIX 43 H4 2 0.329629 0.770403 0.378794 11.00000 -1.20000 AFIX 0 C5 1 0.023142 0.825553 0.355523 11.00000 0.02980 0.02362 = 0.02269 -0.00088 0.00505 -0.00291 C6 1 -0.134746 0.839718 0.298823 11.00000 0.02781 0.02817 = 0.02530 -0.00122 0.00806 0.00203 AFIX 43 H6 2 -0.262651 0.872969 0.305056 11.00000 -1.20000 AFIX 0 C7 1 -0.128538 0.822868 0.093313 11.00000 0.02555 0.03106 = 0.02089 -0.00513 0.00327 0.00017 C8 1 0.063502 0.771979 0.095959 11.00000 0.02958 0.02722 = 0.02190 -0.00323 0.00099 0.00015 C9 1 0.199464 0.774941 0.040165 11.00000 0.02864 0.03117 = 0.02902 -0.00336 0.00546 0.00438 AFIX 43 H9 2 0.332554 0.742781 0.041700 11.00000 -1.20000 AFIX 0 C10 1 0.142178 0.824511 -0.017713 11.00000 0.03245 0.03710 = 0.02612 -0.00205 0.00873 -0.00077 AFIX 43 H10 2 0.235264 0.824168 -0.055282 11.00000 -1.20000 AFIX 0 C11 1 -0.051558 0.875215 -0.021557 11.00000 0.03248 0.03511 = 0.02401 -0.00022 0.00337 -0.00054 C12 1 -0.184521 0.873981 0.036187 11.00000 0.02604 0.03328 = 0.02653 -0.00230 0.00138 0.00235 AFIX 43 H12 2 -0.313350 0.908364 0.036019 11.00000 -1.20000 AFIX 0 C13 1 0.175946 0.635847 0.148980 11.00000 0.03806 0.02933 = 0.02726 -0.00483 0.00496 0.00546 C14 1 0.205940 0.496760 0.196645 11.00000 0.04908 0.02919 = 0.04060 -0.00466 0.00288 0.00354 AFIX 137 H14A 2 0.131966 0.465524 0.158095 11.00000 -1.50000 H14B 2 0.182894 0.468073 0.240154 11.00000 -1.50000 H14C 2 0.366279 0.500437 0.190503 11.00000 -1.50000 AFIX 0 C15 1 -0.102523 0.589294 0.231028 11.00000 0.04754 0.03927 = 0.05635 -0.00248 0.02352 -0.00462 AFIX 137 H15A 2 -0.075512 0.614475 0.276877 11.00000 -1.50000 H15B 2 -0.169391 0.534017 0.235587 11.00000 -1.50000 H15C 2 -0.204508 0.624750 0.202296 11.00000 -1.50000 AFIX 0 C16 1 0.174216 0.857842 0.474912 11.00000 0.03978 0.05017 = 0.02354 -0.00413 0.00210 -0.00194 AFIX 137 H16A 2 0.242285 0.802368 0.478891 11.00000 -1.50000 H16B 2 0.117409 0.873529 0.519211 11.00000 -1.50000 H16C 2 0.286479 0.898479 0.462492 11.00000 -1.50000 AFIX 0 C17 1 -0.190814 0.916050 0.429815 11.00000 0.04944 0.05155 = 0.02614 -0.00496 0.00969 0.01305 AFIX 137 H17A 2 -0.162236 0.967291 0.404404 11.00000 -1.50000 H17B 2 -0.198662 0.929035 0.478931 11.00000 -1.50000 H17C 2 -0.332762 0.891644 0.411672 11.00000 -1.50000 AFIX 0 C18 1 0.038958 0.934049 -0.134492 11.00000 0.04412 0.05417 = 0.02925 0.00827 0.00523 -0.00119 AFIX 137 H18A 2 0.171088 0.965964 -0.117703 11.00000 -1.50000 H18B 2 -0.038878 0.963564 -0.173338 11.00000 -1.50000 H18C 2 0.085059 0.878849 -0.149769 11.00000 -1.50000 AFIX 0 C19 1 -0.306503 0.977647 -0.080977 11.00000 0.04463 0.05656 = 0.03791 0.01370 0.00127 0.00893 AFIX 137 H19A 2 -0.439071 0.943368 -0.075287 11.00000 -1.50000 H19B 2 -0.323175 1.006677 -0.125483 11.00000 -1.50000 H19C 2 -0.289904 1.018638 -0.043517 11.00000 -1.50000 AFIX 0 HKLF 4 REM mo_70223a in P2(1)/n REM R1 = 0.0461 for 2870 Fo > 4sig(Fo) and 0.0791 for all 4176 data REM 233 parameters refined using 0 restraints END WGHT 0.0369 0.8600 REM Highest difference peak 0.257, deepest hole -0.236, 1-sigma level 0.051 Q1 1 0.0552 0.9891 -0.1467 11.00000 0.05 0.26 ; _shelx_res_checksum 47792 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -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 -0.30927(9) 0.82091(4) 0.16305(3) 0.03196(16) Uani 1 1 d . . N1 N 0.1069(3) 0.71929(10) 0.15574(8) 0.0283(4) Uani 1 1 d . . N2 N 0.1108(3) 0.58123(10) 0.19842(9) 0.0333(4) Uani 1 1 d . . N3 N -0.0098(3) 0.85657(11) 0.42151(9) 0.0318(4) Uani 1 1 d . . N4 N -0.1103(3) 0.92479(13) -0.07897(10) 0.0454(5) Uani 1 1 d . . O1 O 0.2906(3) 0.61292(10) 0.10231(9) 0.0525(5) Uani 1 1 d . . C1 C -0.1046(3) 0.80523(12) 0.23347(10) 0.0254(4) Uani 1 1 d . . C2 C 0.0848(3) 0.75705(12) 0.22244(10) 0.0254(4) Uani 1 1 d . . C3 C 0.2484(3) 0.74726(12) 0.27701(10) 0.0284(5) Uani 1 1 d . . H3 H 0.3822 0.7182 0.2693 0.034 Uiso 1 1 calc R U C4 C 0.2181(3) 0.77942(12) 0.34235(10) 0.0281(4) Uani 1 1 d . . H4 H 0.3296 0.7704 0.3788 0.034 Uiso 1 1 calc R U C5 C 0.0231(3) 0.82555(12) 0.35552(10) 0.0252(4) Uani 1 1 d . . C6 C -0.1347(3) 0.83972(12) 0.29882(10) 0.0268(4) Uani 1 1 d . . H6 H -0.2627 0.8730 0.3051 0.032 Uiso 1 1 calc R U C7 C -0.1285(3) 0.82287(12) 0.09331(10) 0.0258(4) Uani 1 1 d . . C8 C 0.0635(3) 0.77198(12) 0.09596(10) 0.0263(4) Uani 1 1 d . . C9 C 0.1995(3) 0.77494(13) 0.04017(11) 0.0294(5) Uani 1 1 d . . H9 H 0.3326 0.7428 0.0417 0.035 Uiso 1 1 calc R U C10 C 0.1422(4) 0.82451(13) -0.01771(11) 0.0316(5) Uani 1 1 d . . H10 H 0.2353 0.8242 -0.0553 0.038 Uiso 1 1 calc R U C11 C -0.0516(4) 0.87521(13) -0.02156(11) 0.0305(5) Uani 1 1 d . . C12 C -0.1845(3) 0.87398(13) 0.03619(10) 0.0286(4) Uani 1 1 d . . H12 H -0.3133 0.9084 0.0360 0.034 Uiso 1 1 calc R U C13 C 0.1759(4) 0.63585(13) 0.14898(11) 0.0314(5) Uani 1 1 d . . C14 C 0.2059(4) 0.49676(13) 0.19665(12) 0.0396(6) Uani 1 1 d . . H14A H 0.1320 0.4655 0.1581 0.059 Uiso 1 1 calc R U H14B H 0.1829 0.4681 0.2402 0.059 Uiso 1 1 calc R U H14C H 0.3663 0.5004 0.1905 0.059 Uiso 1 1 calc R U C15 C -0.1025(4) 0.58929(15) 0.23103(14) 0.0468(6) Uani 1 1 d . . H15A H -0.0755 0.6145 0.2769 0.070 Uiso 1 1 calc R U H15B H -0.1694 0.5340 0.2356 0.070 Uiso 1 1 calc R U H15C H -0.2045 0.6247 0.2023 0.070 Uiso 1 1 calc R U C16 C 0.1742(4) 0.85784(15) 0.47491(11) 0.0378(5) Uani 1 1 d . . H16A H 0.2423 0.8024 0.4789 0.057 Uiso 1 1 calc R U H16B H 0.1174 0.8735 0.5192 0.057 Uiso 1 1 calc R U H16C H 0.2865 0.8985 0.4625 0.057 Uiso 1 1 calc R U C17 C -0.1908(4) 0.91605(15) 0.42981(12) 0.0420(6) Uani 1 1 d . . H17A H -0.1622 0.9673 0.4044 0.063 Uiso 1 1 calc R U H17B H -0.1987 0.9290 0.4789 0.063 Uiso 1 1 calc R U H17C H -0.3328 0.8916 0.4117 0.063 Uiso 1 1 calc R U C18 C 0.0390(4) 0.93405(16) -0.13449(12) 0.0424(6) Uani 1 1 d . . H18A H 0.1711 0.9660 -0.1177 0.064 Uiso 1 1 calc R U H18B H -0.0389 0.9636 -0.1733 0.064 Uiso 1 1 calc R U H18C H 0.0851 0.8788 -0.1498 0.064 Uiso 1 1 calc R U C19 C -0.3065(4) 0.97765(16) -0.08098(13) 0.0464(6) Uani 1 1 d . . H19A H -0.4391 0.9434 -0.0753 0.070 Uiso 1 1 calc R U H19B H -0.3232 1.0067 -0.1255 0.070 Uiso 1 1 calc R U H19C H -0.2899 1.0186 -0.0435 0.070 Uiso 1 1 calc R U 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 0.0253(3) 0.0478(3) 0.0231(3) -0.0015(2) 0.0036(2) 0.0046(2) N1 0.0361(10) 0.0274(9) 0.0220(9) -0.0020(7) 0.0059(7) 0.0065(7) N2 0.0415(10) 0.0257(9) 0.0340(10) -0.0020(7) 0.0121(8) 0.0032(8) N3 0.0353(10) 0.0388(10) 0.0213(9) -0.0049(7) 0.0032(7) 0.0046(8) N4 0.0450(12) 0.0608(13) 0.0317(11) 0.0162(9) 0.0120(9) 0.0155(10) O1 0.0786(13) 0.0399(9) 0.0430(10) 0.0003(8) 0.0317(9) 0.0208(9) C1 0.0259(10) 0.0280(10) 0.0222(10) -0.0004(8) 0.0020(8) -0.0007(8) C2 0.0298(10) 0.0251(10) 0.0219(10) -0.0032(8) 0.0054(8) 0.0007(8) C3 0.0308(11) 0.0260(10) 0.0287(11) 0.0005(8) 0.0049(9) 0.0059(8) C4 0.0308(11) 0.0288(11) 0.0244(11) 0.0014(8) 0.0001(8) 0.0022(9) C5 0.0298(10) 0.0236(10) 0.0227(10) -0.0009(8) 0.0051(8) -0.0029(8) C6 0.0278(10) 0.0282(10) 0.0253(10) -0.0012(8) 0.0081(8) 0.0020(8) C7 0.0256(10) 0.0311(10) 0.0209(10) -0.0051(8) 0.0033(8) 0.0002(9) C8 0.0296(10) 0.0272(10) 0.0219(10) -0.0032(8) 0.0010(8) 0.0002(8) C9 0.0286(10) 0.0312(11) 0.0290(11) -0.0034(9) 0.0055(9) 0.0044(9) C10 0.0325(11) 0.0371(12) 0.0261(11) -0.0021(9) 0.0087(9) -0.0008(9) C11 0.0325(11) 0.0351(11) 0.0240(11) -0.0002(9) 0.0034(9) -0.0005(9) C12 0.0260(10) 0.0333(11) 0.0265(11) -0.0023(9) 0.0014(8) 0.0023(9) C13 0.0381(12) 0.0293(11) 0.0273(11) -0.0048(9) 0.0050(9) 0.0055(9) C14 0.0491(14) 0.0292(12) 0.0406(14) -0.0047(10) 0.0029(11) 0.0035(10) C15 0.0475(14) 0.0393(13) 0.0564(16) -0.0025(12) 0.0235(13) -0.0046(11) C16 0.0398(13) 0.0502(14) 0.0235(11) -0.0041(10) 0.0021(9) -0.0019(11) C17 0.0494(14) 0.0516(14) 0.0261(12) -0.0050(10) 0.0097(10) 0.0131(11) C18 0.0441(14) 0.0542(15) 0.0292(12) 0.0083(11) 0.0052(10) -0.0012(11) C19 0.0446(14) 0.0566(15) 0.0379(14) 0.0137(12) 0.0013(11) 0.0089(12) 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 C1 S1 C7 99.17(9) C13 N1 C2 121.88(16) C13 N1 C8 121.22(16) C2 N1 C8 116.86(16) C13 N2 C14 116.10(17) C13 N2 C15 122.81(19) C14 N2 C15 116.18(18) C5 N3 C16 120.33(17) C5 N3 C17 119.11(17) C16 N3 C17 116.28(17) C11 N4 C19 120.94(18) C11 N4 C18 121.02(19) C19 N4 C18 117.50(18) C2 C1 C6 120.76(18) C2 C1 S1 118.71(15) C6 C1 S1 120.52(15) C3 C2 C1 118.56(17) C3 C2 N1 121.78(17) C1 C2 N1 119.66(18) C4 C3 C2 121.11(18) C3 C4 C5 121.25(19) N3 C5 C6 121.47(17) N3 C5 C4 121.36(18) C6 C5 C4 117.16(17) C1 C6 C5 120.96(18) C12 C7 C8 121.13(18) C12 C7 S1 118.91(15) C8 C7 S1 119.94(15) C9 C8 C7 118.13(18) C9 C8 N1 123.96(18) C7 C8 N1 117.91(17) C10 C9 C8 121.05(19) C9 C10 C11 121.50(19) N4 C11 C10 121.99(19) N4 C11 C12 120.92(19) C10 C11 C12 117.10(19) C7 C12 C11 121.04(19) O1 C13 N2 121.57(19) O1 C13 N1 122.35(19) N2 C13 N1 116.07(17) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 C1 1.771(2) S1 C7 1.7758(19) N1 C13 1.396(3) N1 C2 1.429(2) N1 C8 1.429(3) N2 C13 1.362(3) N2 C14 1.457(3) N2 C15 1.459(3) N3 C5 1.386(2) N3 C16 1.445(3) N3 C17 1.449(3) N4 C11 1.379(3) N4 C19 1.435(3) N4 C18 1.442(3) O1 C13 1.220(2) C1 C2 1.390(3) C1 C6 1.393(3) C2 C3 1.386(3) C3 C4 1.378(3) C4 C5 1.408(3) C5 C6 1.404(3) C7 C12 1.386(3) C7 C8 1.396(3) C8 C9 1.388(3) C9 C10 1.385(3) C10 C11 1.402(3) C11 C12 1.407(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 C7 S1 C1 C2 -33.49(17) C7 S1 C1 C6 147.27(16) C6 C1 C2 C3 -2.9(3) S1 C1 C2 C3 177.85(15) C6 C1 C2 N1 177.25(17) S1 C1 C2 N1 -2.0(3) C13 N1 C2 C3 45.2(3) C8 N1 C2 C3 -132.4(2) C13 N1 C2 C1 -135.0(2) C8 N1 C2 C1 47.4(3) C1 C2 C3 C4 4.5(3) N1 C2 C3 C4 -175.72(18) C2 C3 C4 C5 -1.9(3) C16 N3 C5 C6 -166.14(19) C17 N3 C5 C6 -10.2(3) C16 N3 C5 C4 13.0(3) C17 N3 C5 C4 168.92(19) C3 C4 C5 N3 178.73(19) C3 C4 C5 C6 -2.1(3) C2 C1 C6 C5 -1.1(3) S1 C1 C6 C5 178.08(15) N3 C5 C6 C1 -177.23(18) C4 C5 C6 C1 3.6(3) C1 S1 C7 C12 -146.78(16) C1 S1 C7 C8 34.66(18) C12 C7 C8 C9 1.0(3) S1 C7 C8 C9 179.56(15) C12 C7 C8 N1 -178.34(18) S1 C7 C8 N1 0.2(3) C13 N1 C8 C9 -42.8(3) C2 N1 C8 C9 134.8(2) C13 N1 C8 C7 136.5(2) C2 N1 C8 C7 -45.9(3) C7 C8 C9 C10 -2.4(3) N1 C8 C9 C10 176.95(19) C8 C9 C10 C11 1.7(3) C19 N4 C11 C10 -178.5(2) C18 N4 C11 C10 -7.1(3) C19 N4 C11 C12 1.1(3) C18 N4 C11 C12 172.5(2) C9 C10 C11 N4 -179.9(2) C9 C10 C11 C12 0.4(3) C8 C7 C12 C11 1.1(3) S1 C7 C12 C11 -177.48(16) N4 C11 C12 C7 178.6(2) C10 C11 C12 C7 -1.8(3) C14 N2 C13 O1 6.4(3) C15 N2 C13 O1 -147.8(2) C14 N2 C13 N1 -172.57(19) C15 N2 C13 N1 33.2(3) C2 N1 C13 O1 -145.8(2) C8 N1 C13 O1 31.7(3) C2 N1 C13 N2 33.1(3) C8 N1 C13 N2 -149.37(19)