#------------------------------------------------------------------------------ #$Date: 2024-10-15 03:42:13 +0300 (Tue, 15 Oct 2024) $ #$Revision: 295488 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/16/01/7160182.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_7160182 loop_ _publ_author_name 'Fesenko, Anastasia' 'Grigoriev, Mikhail S.' 'Shutalev, Anatoly' _publ_section_title ; Effective self-assembly of 21- and 14-membered azamacrocycles via condition-controlled cyclotrimerization or cyclodimerization of different thiosemicarbazide-based precursors ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D4OB01384K _journal_year 2024 _chemical_formula_sum 'C12 H22 N6 S2' _chemical_formula_weight 314.47 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2024-06-10 deposited with the CCDC. 2024-10-14 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 97.306(1) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.7250(3) _cell_length_b 9.1469(2) _cell_length_c 18.4748(5) _cell_measurement_reflns_used 9951 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 29.85 _cell_measurement_theta_min 2.49 _cell_volume 1630.06(8) _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Bruker KAPPA APEX II area-detector diffractometer' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0307 _diffrn_reflns_av_unetI/netI 0.0236 _diffrn_reflns_Laue_measured_fraction_full 0.994 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 31725 _diffrn_reflns_point_group_measured_fraction_full 0.994 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 29.998 _diffrn_reflns_theta_min 3.630 _exptl_absorpt_coefficient_mu 0.327 _exptl_absorpt_correction_T_max 0.746 _exptl_absorpt_correction_T_min 0.670 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 (2015) 3-10 ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.281 _exptl_crystal_description bulk _exptl_crystal_F_000 672 _exptl_crystal_size_max 0.400 _exptl_crystal_size_mid 0.380 _exptl_crystal_size_min 0.340 _refine_diff_density_max 0.630 _refine_diff_density_min -0.394 _refine_diff_density_rms 0.057 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 197 _refine_ls_number_reflns 4733 _refine_ls_number_restraints 4 _refine_ls_restrained_S_all 1.057 _refine_ls_R_factor_all 0.0764 _refine_ls_R_factor_gt 0.0604 _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^)+(0.0720P)^2^+1.1165P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1587 _refine_ls_wR_factor_ref 0.1714 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3686 _reflns_number_total 4733 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ob01384k2.cif _cod_data_source_block L3357 _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7160182 _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. ; _shelx_estimated_absorpt_t_min 0.880 _shelx_estimated_absorpt_t_max 0.897 _shelx_res_file ; TITL L3357_RT in P2(1)/c shelx.res created by SHELXL-2018/3 at 23:09:34 on 01-May-2024 CELL 0.71073 9.7250 9.1469 18.4748 90.000 97.306 90.000 ZERR 4.00 0.0003 0.0002 0.0005 0.000 0.001 0.000 LATT 1 SYMM -x, y+1/2, -z+1/2 SFAC C H N S UNIT 48 88 24 8 TEMP 23.000 SIZE 0.40 0.38 0.34 ACTA CONF L.S. 10 DFIX 0.86 N2 H2 N4 H4 N9 H9 N11 H11 FMAP 2 PLAN 20 HTAB EQIV $1 x-1, y, z HTAB N2 S2_$1 HTAB N4 N8 EQIV $2 x+1, y, z HTAB N9 S1_$2 HTAB N11 N1 HTAB N11 N8 SHEL 6 0.5 OMIT -2 60 OMIT -1 2 3 OMIT 4 3 2 OMIT 1 2 7 OMIT -2 1 9 OMIT -4 3 3 OMIT -1 5 4 OMIT 2 0 4 OMIT 0 2 9 BOND $H WGHT 0.072000 1.116500 FVAR 0.16726 S1 4 -0.151762 0.277166 0.557460 11.00000 0.03053 0.09788 = 0.12767 -0.06659 0.01276 -0.01506 S2 4 0.685982 0.586305 0.692700 11.00000 0.03324 0.04734 = 0.06225 -0.00771 0.00335 -0.00728 N1 3 0.126611 0.542313 0.655562 11.00000 0.03346 0.04955 = 0.07950 -0.02123 0.00294 -0.00451 N2 3 -0.000671 0.483203 0.627820 11.00000 0.02723 0.05471 = 0.07347 -0.02220 0.00548 -0.00208 H2 2 -0.073222 0.516051 0.639194 11.00000 -1.20000 N4 3 0.118827 0.318255 0.568354 11.00000 0.02898 0.06026 = 0.09154 -0.03793 0.00874 -0.00817 H4 2 0.187606 0.373088 0.580890 11.00000 -1.20000 N8 3 0.409358 0.344726 0.574914 11.00000 0.03195 0.06880 = 0.06069 -0.02279 0.00755 -0.00783 N9 3 0.535047 0.405944 0.603948 11.00000 0.02671 0.05574 = 0.05382 -0.01526 0.00557 -0.00209 H9 2 0.610348 0.383999 0.590754 11.00000 -1.20000 N11 3 0.418529 0.523378 0.685286 11.00000 0.03121 0.08539 = 0.06660 -0.03930 0.00816 -0.01186 H11 2 0.352253 0.476953 0.662960 11.00000 -1.20000 C3 1 -0.001909 0.361203 0.585980 11.00000 0.03032 0.05110 = 0.06028 -0.01632 0.00497 -0.00540 C5 1 0.149268 0.181624 0.533273 11.00000 0.03489 0.05502 = 0.05725 -0.02350 0.00642 -0.00510 AFIX 13 H5 2 0.065306 0.151037 0.501910 11.00000 -1.20000 AFIX 0 C6 1 0.263286 0.206720 0.484640 11.00000 0.04724 0.08643 = 0.04886 -0.01776 0.00157 -0.00998 AFIX 23 H6A 2 0.279440 0.114312 0.461382 11.00000 -1.20000 H6B 2 0.226851 0.273765 0.446244 11.00000 -1.20000 AFIX 0 C7 1 0.402506 0.264886 0.517848 11.00000 0.03882 0.06071 = 0.04434 -0.00807 0.00272 -0.00058 C10 1 0.537380 0.501383 0.659833 11.00000 0.03035 0.04001 = 0.04357 -0.00106 -0.00003 -0.00055 C12 1 0.390163 0.619748 0.744049 11.00000 0.03605 0.05697 = 0.05661 -0.02212 0.00324 -0.00403 AFIX 13 H12 2 0.473510 0.678294 0.758564 11.00000 -1.20000 AFIX 0 C13 1 0.273400 0.722820 0.719389 11.00000 0.04998 0.04296 = 0.09371 -0.01196 -0.00511 -0.00858 AFIX 23 H13A 2 0.302680 0.783929 0.681254 11.00000 -1.20000 H13B 2 0.261499 0.786466 0.760127 11.00000 -1.20000 AFIX 0 C14 1 0.132718 0.660729 0.691097 11.00000 0.03974 0.04292 = 0.06509 -0.00806 0.00159 -0.00179 C15 1 0.185791 0.064040 0.588768 11.00000 0.09162 0.06596 = 0.08289 -0.01056 0.02235 -0.01041 AFIX 137 H15A 2 0.112184 0.053575 0.618428 11.00000 -1.50000 H15B 2 0.269891 0.089817 0.619078 11.00000 -1.50000 H15C 2 0.198716 -0.026670 0.564382 11.00000 -1.50000 AFIX 0 C16 1 0.520465 0.227449 0.478602 11.00000 0.04531 0.08919 = 0.05691 -0.02393 0.00177 0.00698 AFIX 137 H16A 2 0.578805 0.311642 0.476613 11.00000 -1.50000 H16B 2 0.486582 0.196691 0.429909 11.00000 -1.50000 H16C 2 0.572874 0.149619 0.503710 11.00000 -1.50000 AFIX 0 C17 1 0.363514 0.527388 0.808862 11.00000 0.09911 0.08408 = 0.06213 -0.00563 0.00485 0.00901 AFIX 137 H17A 2 0.441198 0.463919 0.822280 11.00000 -1.50000 H17B 2 0.281485 0.469771 0.796156 11.00000 -1.50000 H17C 2 0.350968 0.589929 0.849234 11.00000 -1.50000 AFIX 0 C18 1 0.011361 0.749435 0.706746 11.00000 0.04978 0.07976 = 0.15299 -0.06124 0.00852 -0.00220 AFIX 137 H18A 2 -0.054945 0.755073 0.663657 11.00000 -1.50000 H18B 2 0.041695 0.846123 0.721334 11.00000 -1.50000 H18C 2 -0.030831 0.704242 0.745324 11.00000 -1.50000 AFIX 0 HKLF 4 REM L3357_RT in P2(1)/c REM wR2 = 0.1714, GooF = S = 1.057, Restrained GooF = 1.057 for all data REM R1 = 0.0604 for 3686 Fo > 4sig(Fo) and 0.0764 for all 4733 data REM 197 parameters refined using 4 restraints END WGHT 0.0720 1.1165 REM Instructions for potential hydrogen bonds HTAB N2 S2_$1 HTAB N4 N8 HTAB N9 S1_$2 HTAB N11 N1 HTAB N11 N8 HTAB C12 S2 EQIV $3 -x+1, y+1/2, -z+3/2 HTAB C13 S2_$3 HTAB C16 S1_$2 HTAB C18 S2_$1 REM Highest difference peak 0.630, deepest hole -0.394, 1-sigma level 0.057 Q1 1 0.4007 0.2020 0.5594 11.00000 0.05 0.63 Q2 1 0.2822 0.1002 0.5633 11.00000 0.05 0.61 Q3 1 0.4187 0.2894 0.6157 11.00000 0.05 0.60 Q4 1 -0.1163 0.2432 0.5934 11.00000 0.05 0.50 Q5 1 0.1198 0.2066 0.4538 11.00000 0.05 0.50 Q6 1 -0.1201 0.3270 0.5339 11.00000 0.05 0.40 Q7 1 0.6443 0.6072 0.6582 11.00000 0.05 0.37 Q8 1 0.1251 0.5787 0.7277 11.00000 0.05 0.36 Q9 1 0.0257 0.6617 0.7475 11.00000 0.05 0.35 Q10 1 0.6122 0.5353 0.6681 11.00000 0.05 0.33 Q11 1 0.1204 0.4568 0.6920 11.00000 0.05 0.33 Q12 1 0.2663 0.5875 0.7848 11.00000 0.05 0.28 Q13 1 0.4662 0.2005 0.4994 11.00000 0.05 0.27 Q14 1 0.6432 0.5675 0.7142 11.00000 0.05 0.27 Q15 1 0.3476 0.7734 0.6905 11.00000 0.05 0.27 Q16 1 0.0946 0.2720 0.6062 11.00000 0.05 0.27 Q17 1 -0.1875 0.2540 0.5497 11.00000 0.05 0.27 Q18 1 -0.0632 0.3141 0.5702 11.00000 0.05 0.26 Q19 1 0.4786 0.5324 0.6674 11.00000 0.05 0.25 Q20 1 0.3574 0.6705 0.7186 11.00000 0.05 0.25 ; _shelx_res_checksum 70275 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S1 S -0.15176(6) 0.27717(10) 0.55746(6) 0.0851(3) Uani 1 1 d . . . . . S2 S 0.68598(5) 0.58630(6) 0.69270(3) 0.04785(17) Uani 1 1 d . . . . . N1 N 0.12661(19) 0.5423(2) 0.65556(13) 0.0545(5) Uani 1 1 d . . . . . N2 N -0.00067(18) 0.4832(2) 0.62782(12) 0.0519(5) Uani 1 1 d D . . . . H2 H -0.073(2) 0.516(3) 0.6392(15) 0.062 Uiso 1 1 d D U . . . N4 N 0.11883(19) 0.3183(2) 0.56835(14) 0.0602(6) Uani 1 1 d D . . . . H4 H 0.188(3) 0.373(3) 0.5809(17) 0.072 Uiso 1 1 d D U . . . N8 N 0.40936(18) 0.3447(2) 0.57491(11) 0.0537(5) Uani 1 1 d . . . . . N9 N 0.53505(17) 0.4059(2) 0.60395(10) 0.0454(4) Uani 1 1 d D . . . . H9 H 0.610(2) 0.384(3) 0.5908(14) 0.054 Uiso 1 1 d D U . . . N11 N 0.41853(19) 0.5234(3) 0.68529(12) 0.0609(6) Uani 1 1 d D . . . . H11 H 0.352(3) 0.477(3) 0.6630(16) 0.073 Uiso 1 1 d D U . . . C3 C -0.0019(2) 0.3612(3) 0.58598(13) 0.0473(5) Uani 1 1 d . . . . . C5 C 0.1493(2) 0.1816(3) 0.53327(13) 0.0490(5) Uani 1 1 d . . . . . H5 H 0.065306 0.151037 0.501910 0.059 Uiso 1 1 calc R U . . . C6 C 0.2633(3) 0.2067(4) 0.48464(14) 0.0612(7) Uani 1 1 d . . . . . H6A H 0.279440 0.114312 0.461382 0.073 Uiso 1 1 calc R U . . . H6B H 0.226851 0.273765 0.446244 0.073 Uiso 1 1 calc R U . . . C7 C 0.4025(2) 0.2649(3) 0.51785(12) 0.0482(5) Uani 1 1 d . . . . . C10 C 0.53738(19) 0.5014(2) 0.65983(11) 0.0384(4) Uani 1 1 d . . . . . C12 C 0.3902(2) 0.6197(3) 0.74405(13) 0.0501(5) Uani 1 1 d . . . . . H12 H 0.473510 0.678294 0.758564 0.060 Uiso 1 1 calc R U . . . C13 C 0.2734(3) 0.7228(3) 0.71939(18) 0.0634(7) Uani 1 1 d . . . . . H13A H 0.302680 0.783929 0.681254 0.076 Uiso 1 1 calc R U . . . H13B H 0.261499 0.786466 0.760127 0.076 Uiso 1 1 calc R U . . . C14 C 0.1327(2) 0.6607(3) 0.69110(14) 0.0497(5) Uani 1 1 d . . . . . C15 C 0.1858(4) 0.0640(4) 0.58877(19) 0.0792(9) Uani 1 1 d . . . . . H15A H 0.112184 0.053575 0.618428 0.119 Uiso 1 1 calc R U . . . H15B H 0.269891 0.089817 0.619078 0.119 Uiso 1 1 calc R U . . . H15C H 0.198716 -0.026670 0.564382 0.119 Uiso 1 1 calc R U . . . C16 C 0.5205(3) 0.2274(4) 0.47860(15) 0.0642(7) Uani 1 1 d . . . . . H16A H 0.578805 0.311642 0.476613 0.096 Uiso 1 1 calc R U . . . H16B H 0.486582 0.196691 0.429909 0.096 Uiso 1 1 calc R U . . . H16C H 0.572874 0.149619 0.503710 0.096 Uiso 1 1 calc R U . . . C17 C 0.3635(4) 0.5274(4) 0.80886(17) 0.0822(9) Uani 1 1 d . . . . . H17A H 0.441198 0.463919 0.822280 0.123 Uiso 1 1 calc R U . . . H17B H 0.281485 0.469771 0.796156 0.123 Uiso 1 1 calc R U . . . H17C H 0.350968 0.589929 0.849234 0.123 Uiso 1 1 calc R U . . . C18 C 0.0114(3) 0.7494(4) 0.7067(3) 0.0946(13) Uani 1 1 d . . . . . H18A H -0.054945 0.755073 0.663657 0.142 Uiso 1 1 calc R U . . . H18B H 0.041695 0.846123 0.721334 0.142 Uiso 1 1 calc R U . . . H18C H -0.030831 0.704242 0.745324 0.142 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 0.0305(3) 0.0979(6) 0.1277(7) -0.0666(5) 0.0128(3) -0.0151(3) S2 0.0332(3) 0.0473(3) 0.0623(3) -0.0077(2) 0.0033(2) -0.0073(2) N1 0.0335(9) 0.0495(10) 0.0795(14) -0.0212(10) 0.0029(8) -0.0045(8) N2 0.0272(8) 0.0547(11) 0.0735(13) -0.0222(10) 0.0055(8) -0.0021(8) N4 0.0290(8) 0.0603(12) 0.0915(16) -0.0379(12) 0.0087(9) -0.0082(8) N8 0.0319(8) 0.0688(13) 0.0607(11) -0.0228(10) 0.0075(8) -0.0078(9) N9 0.0267(7) 0.0557(11) 0.0538(10) -0.0153(8) 0.0056(7) -0.0021(7) N11 0.0312(9) 0.0854(16) 0.0666(13) -0.0393(12) 0.0082(8) -0.0119(9) C3 0.0303(9) 0.0511(12) 0.0603(13) -0.0163(10) 0.0050(8) -0.0054(8) C5 0.0349(10) 0.0550(13) 0.0573(12) -0.0235(10) 0.0064(9) -0.0051(9) C6 0.0472(12) 0.0864(19) 0.0489(12) -0.0178(12) 0.0016(10) -0.0100(13) C7 0.0388(10) 0.0607(14) 0.0443(10) -0.0081(10) 0.0027(8) -0.0006(9) C10 0.0303(8) 0.0400(10) 0.0436(10) -0.0011(8) 0.0000(7) -0.0005(7) C12 0.0360(10) 0.0570(13) 0.0566(12) -0.0221(10) 0.0032(9) -0.0040(9) C13 0.0500(13) 0.0430(12) 0.094(2) -0.0120(13) -0.0051(13) -0.0086(10) C14 0.0397(10) 0.0429(11) 0.0651(14) -0.0081(10) 0.0016(9) -0.0018(9) C15 0.092(2) 0.0660(18) 0.083(2) -0.0106(16) 0.0224(18) -0.0104(17) C16 0.0453(12) 0.089(2) 0.0569(14) -0.0239(14) 0.0018(10) 0.0070(13) C17 0.099(3) 0.084(2) 0.0621(17) -0.0056(16) 0.0048(16) 0.009(2) C18 0.0498(15) 0.080(2) 0.153(4) -0.061(2) 0.0085(19) -0.0022(14) 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' 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 C14 N1 N2 120.43(19) . . ? C3 N2 N1 118.28(18) . . ? C3 N2 H2 120(2) . . ? N1 N2 H2 121(2) . . ? C3 N4 C5 127.17(19) . . ? C3 N4 H4 117(2) . . ? C5 N4 H4 116(2) . . ? C7 N8 N9 120.02(18) . . ? C10 N9 N8 118.98(17) . . ? C10 N9 H9 117(2) . . ? N8 N9 H9 124(2) . . ? C10 N11 C12 128.19(18) . . ? C10 N11 H11 114(2) . . ? C12 N11 H11 118(2) . . ? N4 C3 N2 116.26(18) . . ? N4 C3 S1 123.59(17) . . ? N2 C3 S1 120.12(16) . . ? N4 C5 C15 110.8(2) . . ? N4 C5 C6 109.6(2) . . ? C15 C5 C6 112.5(2) . . ? N4 C5 H5 107.9 . . ? C15 C5 H5 107.9 . . ? C6 C5 H5 107.9 . . ? C7 C6 C5 119.55(19) . . ? C7 C6 H6A 107.4 . . ? C5 C6 H6A 107.4 . . ? C7 C6 H6B 107.4 . . ? C5 C6 H6B 107.4 . . ? H6A C6 H6B 107.0 . . ? N8 C7 C16 125.2(2) . . ? N8 C7 C6 119.1(2) . . ? C16 C7 C6 115.6(2) . . ? N11 C10 N9 116.20(18) . . ? N11 C10 S2 123.53(16) . . ? N9 C10 S2 120.27(15) . . ? N11 C12 C13 111.3(2) . . ? N11 C12 C17 108.7(2) . . ? C13 C12 C17 113.0(2) . . ? N11 C12 H12 107.9 . . ? C13 C12 H12 107.9 . . ? C17 C12 H12 107.9 . . ? C12 C13 C14 119.0(2) . . ? C12 C13 H13A 107.6 . . ? C14 C13 H13A 107.6 . . ? C12 C13 H13B 107.6 . . ? C14 C13 H13B 107.6 . . ? H13A C13 H13B 107.0 . . ? N1 C14 C18 125.5(2) . . ? N1 C14 C13 118.8(2) . . ? C18 C14 C13 115.6(2) . . ? C5 C15 H15A 109.5 . . ? C5 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C5 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C7 C16 H16A 109.5 . . ? C7 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C7 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C14 C18 H18A 109.5 . . ? C14 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C14 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? 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 C3 1.672(2) . ? S2 C10 1.684(2) . ? N1 C14 1.264(3) . ? N1 N2 1.388(2) . ? N2 C3 1.357(3) . ? N2 H2 0.819(17) . ? N4 C3 1.318(3) . ? N4 C5 1.455(3) . ? N4 H4 0.845(18) . ? N8 C7 1.277(3) . ? N8 N9 1.389(2) . ? N9 C10 1.350(3) . ? N9 H9 0.825(17) . ? N11 C10 1.317(3) . ? N11 C12 1.452(3) . ? N11 H11 0.836(18) . ? C5 C15 1.497(4) . ? C5 C6 1.531(3) . ? C5 H5 0.9800 . ? C6 C7 1.510(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C16 1.473(3) . ? C12 C13 1.501(4) . ? C12 C17 1.514(4) . ? C12 H12 0.9800 . ? C13 C14 1.512(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C18 1.490(4) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? 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 N2 H2 S2 0.819(17) 2.732(18) 3.5413(19) 170(3) 1_455 yes N4 H4 N8 0.845(18) 2.19(3) 2.823(2) 132(3) . yes N9 H9 S1 0.825(17) 2.655(18) 3.4738(18) 172(3) 1_655 yes N11 H11 N1 0.836(18) 2.26(3) 2.827(3) 125(3) . yes N11 H11 N8 0.836(18) 2.16(3) 2.606(3) 114(3) . 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C14 N1 N2 C3 175.7(2) . . . . ? C7 N8 N9 C10 173.5(2) . . . . ? C5 N4 C3 N2 170.6(3) . . . . ? C5 N4 C3 S1 -11.4(4) . . . . ? N1 N2 C3 N4 -7.4(4) . . . . ? N1 N2 C3 S1 174.5(2) . . . . ? C3 N4 C5 C15 -87.8(3) . . . . ? C3 N4 C5 C6 147.4(3) . . . . ? N4 C5 C6 C7 58.6(3) . . . . ? C15 C5 C6 C7 -65.2(3) . . . . ? N9 N8 C7 C16 1.1(4) . . . . ? N9 N8 C7 C6 -176.4(2) . . . . ? C5 C6 C7 N8 -27.6(4) . . . . ? C5 C6 C7 C16 154.6(3) . . . . ? C12 N11 C10 N9 -179.5(3) . . . . ? C12 N11 C10 S2 -0.2(4) . . . . ? N8 N9 C10 N11 3.4(3) . . . . ? N8 N9 C10 S2 -175.90(17) . . . . ? C10 N11 C12 C13 125.7(3) . . . . ? C10 N11 C12 C17 -109.2(3) . . . . ? N11 C12 C13 C14 59.6(3) . . . . ? C17 C12 C13 C14 -63.1(3) . . . . ? N2 N1 C14 C18 -0.6(5) . . . . ? N2 N1 C14 C13 -179.0(2) . . . . ? C12 C13 C14 N1 -34.6(4) . . . . ? C12 C13 C14 C18 146.9(3) . . . . ?