#------------------------------------------------------------------------------ #$Date: 2019-11-08 02:08:07 +0200 (Fri, 08 Nov 2019) $ #$Revision: 224671 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/05/85/7058506.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_7058506 loop_ _publ_author_name 'Kundu, Bidyut Kumar' 'Pragti, Pragti' 'Reena, Reena' 'Mobin, Shaikh M.' 'Mukhopadhyay, Suman' _publ_section_title ; Mechanistic and thermodynamic aspects of a pyrene-based fluorescent probe to detect picric acid ; _journal_issue 29 _journal_name_full 'New Journal of Chemistry' _journal_page_first 11483 _journal_paper_doi 10.1039/C9NJ02342A _journal_volume 43 _journal_year 2019 _chemical_formula_sum 'C22 H14 N2 O S' _chemical_formula_weight 354.41 _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' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2018-08-13 deposited with the CCDC. 2019-06-19 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 99.643(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 13.6604(4) _cell_length_b 10.0147(3) _cell_length_c 12.6251(3) _cell_measurement_reflns_used 3954 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 26.8350 _cell_measurement_theta_min 3.9250 _cell_volume 1702.77(8) _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.,' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_molecular_graphics Ortep3 _computing_publication_material Shelx97 _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 15.9948 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.901 _diffrn_measurement_device_type 'OXFORD DIFFRACTION SUPER NOVA' _diffrn_measurement_method \w/q-scan _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Micro-Focus (Mo) X-ray Source' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0465 _diffrn_reflns_av_unetI/netI 0.0450 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.901 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 15958 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.901 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 29.009 _diffrn_reflns_theta_min 2.876 _exptl_absorpt_coefficient_mu 0.203 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.69668 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour COLORLESS _exptl_crystal_density_diffrn 1.382 _exptl_crystal_density_method 'not measured' _exptl_crystal_description BLOCK _exptl_crystal_F_000 736 _exptl_crystal_size_max 0.330 _exptl_crystal_size_mid 0.260 _exptl_crystal_size_min 0.210 _refine_diff_density_max 0.577 _refine_diff_density_min -0.729 _refine_diff_density_rms 0.185 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 235 _refine_ls_number_reflns 4083 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.083 _refine_ls_R_factor_all 0.1423 _refine_ls_R_factor_gt 0.0849 _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^)+(0.1840P)^2^+0.3696P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2467 _refine_ls_wR_factor_ref 0.3153 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2444 _reflns_number_total 4083 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9nj02342a2.cif _cod_data_source_block shelx _cod_depositor_comments 'Adding full bibliography for 7058506.cif.' _cod_database_code 7058506 _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 0.936 _shelx_estimated_absorpt_t_max 0.959 _shelx_res_file ; shelx.res created by SHELXL-2014/7 TITL shelxt_a.res in P2(1)/c CELL 0.71073 13.6604 10.0147 12.6251 90.000 99.643 90.000 ZERR 4.00 0.0004 0.0003 0.0003 0.000 0.003 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N O S UNIT 88 56 8 4 4 MERG 2 FMAP 2 PLAN 20 SIZE 0.210 0.260 0.330 ACTA BOND $H CONF LIST 6 L.S. 16 WGHT 0.184000 0.369600 FVAR 4.51282 S1 5 0.857868 0.922443 0.374347 11.00000 0.07074 0.08147 = 0.13030 0.03540 0.03227 0.01697 O1 4 1.060312 0.639774 0.453793 11.00000 0.04472 0.06886 = 0.09153 0.00750 0.01878 0.01038 N1 3 0.909427 0.643054 0.498879 11.00000 0.04806 0.05777 = 0.07813 0.01115 0.01946 0.01093 AFIX 43 H1N 2 0.921364 0.567563 0.530910 11.00000 -1.20000 AFIX 0 N2 3 0.818792 0.702234 0.496888 11.00000 0.04547 0.05203 = 0.06311 0.00170 0.01519 0.00716 C1 1 0.911312 1.040508 0.308557 11.00000 0.08096 0.08362 = 0.12082 0.03318 0.02174 0.00655 AFIX 43 H1 2 0.878171 1.116608 0.279474 11.00000 -1.20000 AFIX 0 C2 1 1.005818 1.014469 0.302115 11.00000 0.07472 0.11091 = 0.11235 0.04803 0.02541 -0.00212 AFIX 43 H2 2 1.044469 1.071911 0.268499 11.00000 -1.20000 AFIX 0 C3 1 1.043477 0.891611 0.350726 11.00000 0.07124 0.08206 = 0.08024 0.03613 0.01996 0.00872 AFIX 43 H3 2 1.106983 0.857450 0.352095 11.00000 -1.20000 AFIX 0 C4 1 0.964898 0.830429 0.397224 11.00000 0.04895 0.06277 = 0.05800 0.00173 0.01010 0.00350 C5 1 0.980751 0.700778 0.451503 11.00000 0.04748 0.06085 = 0.05699 -0.00197 0.00931 0.00090 C6 1 0.755436 0.634046 0.538670 11.00000 0.05314 0.04502 = 0.05469 0.00367 0.01521 0.00730 AFIX 43 H6 2 0.774161 0.552920 0.571830 11.00000 -1.20000 AFIX 0 C7 1 0.654314 0.682828 0.534533 11.00000 0.05162 0.03746 = 0.04408 -0.00143 0.01237 0.00359 C8 1 0.621934 0.793513 0.469855 11.00000 0.05834 0.04076 = 0.05210 0.00378 0.01660 -0.00125 AFIX 43 H8 2 0.666784 0.836859 0.433767 11.00000 -1.20000 AFIX 0 C9 1 0.526596 0.839563 0.458258 11.00000 0.05655 0.03906 = 0.05379 0.00866 0.01141 0.00649 AFIX 43 H9 2 0.508048 0.913630 0.415111 11.00000 -1.20000 AFIX 0 C10 1 0.456244 0.776570 0.510604 11.00000 0.04807 0.03559 = 0.04676 0.00104 0.00300 0.00033 C11 1 0.355537 0.819654 0.498153 11.00000 0.05472 0.04501 = 0.06194 0.01167 0.00298 0.00843 AFIX 43 H11 2 0.335410 0.892028 0.453648 11.00000 -1.20000 AFIX 0 C12 1 0.288640 0.758749 0.548877 11.00000 0.04531 0.05677 = 0.06940 0.00411 0.00055 0.00670 AFIX 43 H12 2 0.223601 0.789895 0.538686 11.00000 -1.20000 AFIX 0 C13 1 0.315698 0.647456 0.617873 11.00000 0.04555 0.04612 = 0.05126 -0.00265 0.00544 -0.00358 C14 1 0.248425 0.581453 0.672085 11.00000 0.04520 0.06373 = 0.06433 -0.00071 0.00881 -0.00433 AFIX 43 H14 2 0.183321 0.611863 0.664897 11.00000 -1.20000 AFIX 0 C15 1 0.277278 0.472231 0.735848 11.00000 0.06157 0.07016 = 0.05938 0.00498 0.01927 -0.01415 AFIX 43 H15 2 0.231143 0.429464 0.770537 11.00000 -1.20000 AFIX 0 C16 1 0.373477 0.425053 0.749214 11.00000 0.06440 0.05316 = 0.04660 0.00880 0.01298 -0.00591 AFIX 43 H16 2 0.391219 0.350631 0.792217 11.00000 -1.20000 AFIX 0 C17 1 0.444894 0.488465 0.698419 11.00000 0.05560 0.03843 = 0.03930 0.00043 0.00734 -0.00204 C18 1 0.545476 0.443061 0.710070 11.00000 0.06255 0.04123 = 0.04610 0.00907 0.00807 0.00659 AFIX 43 H18 2 0.565211 0.369917 0.753855 11.00000 -1.20000 AFIX 0 C19 1 0.612317 0.504074 0.658904 11.00000 0.04823 0.04315 = 0.04652 0.00229 0.00776 0.01010 AFIX 43 H19 2 0.676971 0.471557 0.668515 11.00000 -1.20000 AFIX 0 C20 1 0.587061 0.617329 0.590221 11.00000 0.04590 0.03194 = 0.03790 -0.00362 0.00600 0.00112 C21 1 0.486734 0.665092 0.577456 11.00000 0.04688 0.03213 = 0.03691 -0.00525 0.00516 -0.00206 C22 1 0.416312 0.599993 0.632130 11.00000 0.04860 0.03675 = 0.03937 -0.00336 0.00571 -0.00334 HKLF 4 REM shelxt_a.res in P2(1)/c REM R1 = 0.0849 for 2444 Fo > 4sig(Fo) and 0.1423 for all 4083 data REM 235 parameters refined using 0 restraints END WGHT 0.1838 0.3696 REM Highest difference peak 0.577, deepest hole -0.729, 1-sigma level 0.185 Q1 1 0.6470 0.7244 0.5231 11.00000 0.05 0.54 Q2 1 0.6423 0.7896 0.4924 11.00000 0.05 0.52 Q3 1 0.7131 0.8748 0.5245 11.00000 0.05 0.42 Q4 1 0.2727 0.3738 0.8995 11.00000 0.05 0.42 Q5 1 0.6989 0.4557 0.6988 11.00000 0.05 0.42 Q6 1 0.2774 1.0227 0.4200 11.00000 0.05 0.41 Q7 1 1.1918 0.9175 0.3609 11.00000 0.05 0.40 Q8 1 1.0000 0.5000 0.5000 10.50000 0.05 0.40 Q9 1 0.7011 0.8179 0.5791 11.00000 0.05 0.39 Q10 1 0.2820 1.0255 0.4715 11.00000 0.05 0.39 Q11 1 0.2522 0.7490 0.3232 11.00000 0.05 0.37 Q12 1 0.7058 0.9545 0.5037 11.00000 0.05 0.37 Q13 1 0.6787 0.3733 0.6635 11.00000 0.05 0.37 Q14 1 0.2073 0.5052 0.8635 11.00000 0.05 0.37 Q15 1 0.2449 0.4361 0.8637 11.00000 0.05 0.36 Q16 1 0.7353 0.7717 0.6024 11.00000 0.05 0.36 Q17 1 0.7281 0.3556 0.6483 11.00000 0.05 0.35 Q18 1 0.8225 1.2294 0.2101 11.00000 0.05 0.35 Q19 1 1.0672 0.8578 0.3406 11.00000 0.05 0.35 Q20 1 0.9207 0.5204 0.5097 11.00000 0.05 0.34 ; _shelx_res_checksum 85000 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 S1 S 0.85787(9) 0.92244(13) 0.37435(12) 0.0924(5) Uani 1 1 d . . O1 O 1.06031(16) 0.6398(3) 0.4538(2) 0.0675(7) Uani 1 1 d . . N1 N 0.9094(2) 0.6431(3) 0.4989(2) 0.0603(8) Uani 1 1 d . . H1N H 0.9214 0.5676 0.5309 0.072 Uiso 1 1 calc R U N2 N 0.81879(19) 0.7022(3) 0.4969(2) 0.0528(7) Uani 1 1 d . . C1 C 0.9113(4) 1.0405(5) 0.3086(4) 0.0946(15) Uani 1 1 d . . H1 H 0.8782 1.1166 0.2795 0.113 Uiso 1 1 calc R U C2 C 1.0058(3) 1.0145(5) 0.3021(4) 0.0982(16) Uani 1 1 d . . H2 H 1.0445 1.0719 0.2685 0.118 Uiso 1 1 calc R U C3 C 1.0435(3) 0.8916(5) 0.3507(3) 0.0770(12) Uani 1 1 d . . H3 H 1.1070 0.8575 0.3521 0.092 Uiso 1 1 calc R U C4 C 0.9649(2) 0.8304(4) 0.3972(3) 0.0564(8) Uani 1 1 d . . C5 C 0.9808(2) 0.7008(4) 0.4515(3) 0.0550(8) Uani 1 1 d . . C6 C 0.7554(2) 0.6340(3) 0.5387(3) 0.0502(7) Uani 1 1 d . . H6 H 0.7742 0.5529 0.5718 0.060 Uiso 1 1 calc R U C7 C 0.6543(2) 0.6828(3) 0.5345(2) 0.0439(7) Uani 1 1 d . . C8 C 0.6219(2) 0.7935(3) 0.4699(2) 0.0496(7) Uani 1 1 d . . H8 H 0.6668 0.8369 0.4338 0.059 Uiso 1 1 calc R U C9 C 0.5266(2) 0.8396(3) 0.4583(2) 0.0495(7) Uani 1 1 d . . H9 H 0.5080 0.9136 0.4151 0.059 Uiso 1 1 calc R U C10 C 0.4562(2) 0.7766(3) 0.5106(2) 0.0440(7) Uani 1 1 d . . C11 C 0.3555(2) 0.8197(3) 0.4982(3) 0.0547(8) Uani 1 1 d . . H11 H 0.3354 0.8920 0.4536 0.066 Uiso 1 1 calc R U C12 C 0.2886(2) 0.7587(3) 0.5489(3) 0.0582(9) Uani 1 1 d . . H12 H 0.2236 0.7899 0.5387 0.070 Uiso 1 1 calc R U C13 C 0.3157(2) 0.6475(3) 0.6179(2) 0.0480(7) Uani 1 1 d . . C14 C 0.2484(2) 0.5815(4) 0.6721(3) 0.0578(9) Uani 1 1 d . . H14 H 0.1833 0.6119 0.6649 0.069 Uiso 1 1 calc R U C15 C 0.2773(3) 0.4722(4) 0.7358(3) 0.0627(9) Uani 1 1 d . . H15 H 0.2311 0.4295 0.7705 0.075 Uiso 1 1 calc R U C16 C 0.3735(3) 0.4251(3) 0.7492(2) 0.0543(8) Uani 1 1 d . . H16 H 0.3912 0.3506 0.7922 0.065 Uiso 1 1 calc R U C17 C 0.4449(2) 0.4885(3) 0.6984(2) 0.0445(7) Uani 1 1 d . . C18 C 0.5455(2) 0.4431(3) 0.7101(2) 0.0501(8) Uani 1 1 d . . H18 H 0.5652 0.3699 0.7539 0.060 Uiso 1 1 calc R U C19 C 0.6123(2) 0.5041(3) 0.6589(2) 0.0460(7) Uani 1 1 d . . H19 H 0.6770 0.4716 0.6685 0.055 Uiso 1 1 calc R U C20 C 0.5871(2) 0.6173(3) 0.5902(2) 0.0387(6) Uani 1 1 d . . C21 C 0.4867(2) 0.6651(3) 0.5775(2) 0.0389(6) Uani 1 1 d . . C22 C 0.4163(2) 0.6000(3) 0.6321(2) 0.0418(7) 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 0.0707(8) 0.0815(9) 0.1303(11) 0.0354(7) 0.0323(7) 0.0170(5) O1 0.0447(13) 0.0689(16) 0.0915(18) 0.0075(14) 0.0188(12) 0.0104(11) N1 0.0481(15) 0.0578(18) 0.0781(19) 0.0111(14) 0.0195(14) 0.0109(12) N2 0.0455(14) 0.0520(15) 0.0631(16) 0.0017(12) 0.0152(12) 0.0072(12) C1 0.081(3) 0.084(3) 0.121(4) 0.033(3) 0.022(3) 0.007(2) C2 0.075(3) 0.111(4) 0.112(4) 0.048(3) 0.025(3) -0.002(3) C3 0.071(3) 0.082(3) 0.080(3) 0.036(2) 0.020(2) 0.009(2) C4 0.0489(18) 0.063(2) 0.0580(18) 0.0017(16) 0.0101(14) 0.0035(15) C5 0.0475(17) 0.061(2) 0.0570(18) -0.0020(15) 0.0093(14) 0.0009(14) C6 0.0531(17) 0.0450(17) 0.0547(17) 0.0037(14) 0.0152(14) 0.0073(14) C7 0.0516(17) 0.0375(15) 0.0441(15) -0.0014(12) 0.0124(13) 0.0036(12) C8 0.0583(18) 0.0408(16) 0.0521(17) 0.0038(13) 0.0166(14) -0.0012(14) C9 0.0565(18) 0.0391(15) 0.0538(17) 0.0087(13) 0.0114(14) 0.0065(13) C10 0.0481(15) 0.0356(15) 0.0468(15) 0.0010(12) 0.0030(12) 0.0003(12) C11 0.0547(18) 0.0450(17) 0.0619(19) 0.0117(14) 0.0030(15) 0.0084(14) C12 0.0453(17) 0.057(2) 0.069(2) 0.0041(16) 0.0005(15) 0.0067(14) C13 0.0455(16) 0.0461(17) 0.0513(16) -0.0027(13) 0.0054(13) -0.0036(13) C14 0.0452(17) 0.064(2) 0.064(2) -0.0007(16) 0.0088(15) -0.0043(14) C15 0.062(2) 0.070(2) 0.059(2) 0.0050(17) 0.0193(17) -0.0142(18) C16 0.064(2) 0.0532(19) 0.0466(17) 0.0088(14) 0.0130(15) -0.0059(15) C17 0.0556(17) 0.0384(15) 0.0393(14) 0.0004(12) 0.0073(12) -0.0020(12) C18 0.0625(19) 0.0412(16) 0.0461(16) 0.0091(13) 0.0081(14) 0.0066(14) C19 0.0482(16) 0.0431(17) 0.0465(16) 0.0023(12) 0.0078(13) 0.0101(13) C20 0.0459(15) 0.0319(13) 0.0379(14) -0.0036(11) 0.0060(11) 0.0011(11) C21 0.0469(15) 0.0321(13) 0.0369(13) -0.0053(11) 0.0052(11) -0.0021(11) C22 0.0486(16) 0.0367(14) 0.0394(14) -0.0034(11) 0.0057(12) -0.0033(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 C4 91.9(2) C5 N1 N2 121.5(3) C5 N1 H1N 119.3 N2 N1 H1N 119.3 C6 N2 N1 115.6(3) C2 C1 S1 113.4(4) C2 C1 H1 123.3 S1 C1 H1 123.3 C1 C2 C3 115.1(4) C1 C2 H2 122.5 C3 C2 H2 122.5 C2 C3 C4 107.5(4) C2 C3 H3 126.2 C4 C3 H3 126.2 C3 C4 C5 120.3(3) C3 C4 S1 112.0(3) C5 C4 S1 127.6(2) O1 C5 N1 118.1(3) O1 C5 C4 120.4(3) N1 C5 C4 121.5(3) N2 C6 C7 120.5(3) N2 C6 H6 119.8 C7 C6 H6 119.8 C8 C7 C20 119.3(3) C8 C7 C6 119.3(3) C20 C7 C6 121.3(3) C9 C8 C7 122.1(3) C9 C8 H8 119.0 C7 C8 H8 119.0 C8 C9 C10 120.9(3) C8 C9 H9 119.6 C10 C9 H9 119.6 C9 C10 C21 118.5(3) C9 C10 C11 122.4(3) C21 C10 C11 119.0(3) C12 C11 C10 122.0(3) C12 C11 H11 119.0 C10 C11 H11 119.0 C11 C12 C13 121.2(3) C11 C12 H12 119.4 C13 C12 H12 119.4 C14 C13 C12 122.9(3) C14 C13 C22 118.4(3) C12 C13 C22 118.7(3) C15 C14 C13 120.9(3) C15 C14 H14 119.5 C13 C14 H14 119.5 C14 C15 C16 121.1(3) C14 C15 H15 119.4 C16 C15 H15 119.4 C15 C16 C17 120.6(3) C15 C16 H16 119.7 C17 C16 H16 119.7 C16 C17 C22 118.9(3) C16 C17 C18 122.5(3) C22 C17 C18 118.6(3) C19 C18 C17 121.4(3) C19 C18 H18 119.3 C17 C18 H18 119.3 C18 C19 C20 122.3(3) C18 C19 H19 118.9 C20 C19 H19 118.9 C7 C20 C19 124.0(3) C7 C20 C21 118.6(2) C19 C20 C21 117.4(2) C10 C21 C22 119.4(3) C10 C21 C20 120.6(2) C22 C21 C20 120.0(2) C17 C22 C21 120.3(3) C17 C22 C13 120.0(3) C21 C22 C13 119.7(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 C1 1.681(5) S1 C4 1.711(3) O1 C5 1.243(4) N1 C5 1.355(4) N1 N2 1.369(3) N1 H1N 0.8600 N2 C6 1.283(4) C1 C2 1.333(6) C1 H1 0.9300 C2 C3 1.432(6) C2 H2 0.9300 C3 C4 1.443(5) C3 H3 0.9300 C4 C5 1.467(5) C6 C7 1.458(4) C6 H6 0.9300 C7 C8 1.404(4) C7 C20 1.409(4) C8 C9 1.366(4) C8 H8 0.9300 C9 C10 1.404(4) C9 H9 0.9300 C10 C21 1.419(4) C10 C11 1.425(4) C11 C12 1.347(5) C11 H11 0.9300 C12 C13 1.425(4) C12 H12 0.9300 C13 C14 1.400(4) C13 C22 1.437(4) C14 C15 1.376(5) C14 H14 0.9300 C15 C16 1.380(5) C15 H15 0.9300 C16 C17 1.406(4) C16 H16 0.9300 C17 C22 1.411(4) C17 C18 1.431(4) C18 C19 1.350(4) C18 H18 0.9300 C19 C20 1.434(4) C19 H19 0.9300 C20 C21 1.435(4) C21 C22 1.432(4) 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 C5 N1 N2 C6 175.8(3) C4 S1 C1 C2 0.3(5) S1 C1 C2 C3 0.7(7) C1 C2 C3 C4 -1.5(6) C2 C3 C4 C5 178.8(4) C2 C3 C4 S1 1.7(5) C1 S1 C4 C3 -1.2(4) C1 S1 C4 C5 -178.1(4) N2 N1 C5 O1 -178.0(3) N2 N1 C5 C4 1.0(5) C3 C4 C5 O1 -3.2(5) S1 C4 C5 O1 173.5(3) C3 C4 C5 N1 177.8(3) S1 C4 C5 N1 -5.5(5) N1 N2 C6 C7 -175.8(3) N2 C6 C7 C8 10.2(5) N2 C6 C7 C20 -172.7(3) C20 C7 C8 C9 -0.6(5) C6 C7 C8 C9 176.5(3) C7 C8 C9 C10 -0.5(5) C8 C9 C10 C21 1.0(5) C8 C9 C10 C11 -178.3(3) C9 C10 C11 C12 -179.9(3) C21 C10 C11 C12 0.8(5) C10 C11 C12 C13 0.0(5) C11 C12 C13 C14 180.0(3) C11 C12 C13 C22 -0.4(5) C12 C13 C14 C15 178.4(3) C22 C13 C14 C15 -1.2(5) C13 C14 C15 C16 0.6(5) C14 C15 C16 C17 0.5(5) C15 C16 C17 C22 -1.0(5) C15 C16 C17 C18 180.0(3) C16 C17 C18 C19 178.8(3) C22 C17 C18 C19 -0.3(5) C17 C18 C19 C20 0.0(5) C8 C7 C20 C19 -179.6(3) C6 C7 C20 C19 3.4(4) C8 C7 C20 C21 1.0(4) C6 C7 C20 C21 -176.0(2) C18 C19 C20 C7 -179.3(3) C18 C19 C20 C21 0.2(4) C9 C10 C21 C22 179.6(3) C11 C10 C21 C22 -1.0(4) C9 C10 C21 C20 -0.6(4) C11 C10 C21 C20 178.8(3) C7 C20 C21 C10 -0.4(4) C19 C20 C21 C10 -179.9(2) C7 C20 C21 C22 179.4(2) C19 C20 C21 C22 -0.1(4) C16 C17 C22 C21 -178.7(3) C18 C17 C22 C21 0.4(4) C16 C17 C22 C13 0.3(4) C18 C17 C22 C13 179.4(3) C10 C21 C22 C17 179.6(2) C20 C21 C22 C17 -0.2(4) C10 C21 C22 C13 0.6(4) C20 C21 C22 C13 -179.2(2) C14 C13 C22 C17 0.8(4) C12 C13 C22 C17 -178.9(3) C14 C13 C22 C21 179.8(3) C12 C13 C22 C21 0.2(4)