#------------------------------------------------------------------------------ #$Date: 2020-04-16 08:17:59 +0300 (Thu, 16 Apr 2020) $ #$Revision: 250838 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/74/7157469.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_7157469 loop_ _publ_author_name 'Kim, Woo Gyum' 'Baek, Seung-yeol' 'Jeong, Seo Yeong' 'Nam, Dongsik' 'Jeon, Ji Hwan' 'Choe, Wonyoung' 'Baik, Mu-Hyun' 'Hong, Sung You' _publ_section_title ; Chemo- and regioselective click reactions through nickel-catalyzed azide--alkyne cycloaddition ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D0OB00579G _journal_year 2020 _chemical_formula_sum 'C28 H23 N3 S' _chemical_formula_weight 433.55 _chemical_name_systematic 6ea _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_Hall '-P 2ac 2ab' _space_group_name_H-M_alt 'P b c a' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2019-12-05 deposited with the CCDC. 2020-04-15 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 13.151(3) _cell_length_b 18.198(4) _cell_length_c 19.461(4) _cell_measurement_reflns_used 5321 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 27.455 _cell_measurement_theta_min 3.065 _cell_volume 4657.4(18) _computing_cell_refinement 'Rigaku Rapid Auto' _computing_data_collection 'Rigaku Rapid Auto' _computing_data_reduction 'Rigaku Rapid Auto' _computing_molecular_graphics ORTEP _computing_publication_material CIFTAB _computing_structure_refinement SHELXL _computing_structure_solution SHELXS _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'imaging plate' _diffrn_measurement_method 'omega scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0545 _diffrn_reflns_av_unetI/netI 0.0289 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 40382 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.455 _diffrn_reflns_theta_min 3.065 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.159 _exptl_absorpt_correction_T_max 0.961 _exptl_absorpt_correction_T_min 0.960 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Rigaku Rapid Auto' _exptl_crystal_colour Brown _exptl_crystal_density_diffrn 1.237 _exptl_crystal_description Block _exptl_crystal_F_000 1824 _exptl_crystal_size_max 0.260 _exptl_crystal_size_mid 0.260 _exptl_crystal_size_min 0.250 _refine_diff_density_max 0.204 _refine_diff_density_min -0.198 _refine_diff_density_rms 0.030 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 289 _refine_ls_number_reflns 5321 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.016 _refine_ls_R_factor_all 0.0923 _refine_ls_R_factor_gt 0.0520 _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^)+(0.0452P)^2^+1.1679P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1038 _refine_ls_wR_factor_ref 0.1171 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3461 _reflns_number_total 5321 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ob00579g2.cif _cod_data_source_block Pbca_a_CCDC1 _cod_depositor_comments ; The following automatic conversions were performed: data item '_exptl_absorpt_correction_type' value 'Multi-scan' was changed to 'multi-scan' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas ; _cod_original_cell_volume 4657.6(16) _cod_database_code 7157469 _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_res_file ; Pbca_a.res created by SHELXL-2014/7 TITL Pbca_a.res in Pbca CELL 0.71073 13.1514 18.1980 19.4609 90.000 90.000 90.000 ZERR 8.000 0.0026 0.0036 0.0039 0.000 0.000 0.000 LATT 1 SYMM 1/2-X, -Y, 1/2+Z SYMM -X, 1/2+Y, 1/2-Z SYMM 1/2+X, 1/2-Y, -Z SFAC C H N S UNIT 224 184 24 8 L.S. 24 ACTA BOND $H FMAP 2 PLAN 5 LIST 6 SIZE 0.26 0.26 0.25 TEMP 25 WGHT 0.045200 1.167900 FVAR 0.24548 C1 1 0.571226 0.568055 0.312477 11.00000 0.04872 0.03530 = 0.04464 0.00539 0.00363 0.00131 C2 1 0.660338 0.578505 0.349292 11.00000 0.05089 0.03890 = 0.04396 0.00277 0.00537 -0.00210 C3 1 0.725468 0.643126 0.360184 11.00000 0.05551 0.04465 = 0.04501 -0.00088 0.01023 -0.00793 C4 1 0.696649 0.713469 0.342449 11.00000 0.06551 0.04703 = 0.11422 0.01187 -0.00075 -0.00811 AFIX 43 H4 2 0.633747 0.721215 0.321851 11.00000 -1.20000 AFIX 0 C5 1 0.760019 0.772686 0.354873 11.00000 0.08038 0.04432 = 0.13911 0.00139 0.01912 -0.01274 AFIX 43 H5 2 0.738823 0.819720 0.342866 11.00000 -1.20000 AFIX 0 C6 1 0.852055 0.763245 0.384129 11.00000 0.08455 0.05980 = 0.08433 -0.01366 0.02264 -0.02987 AFIX 43 H6 2 0.894132 0.803397 0.392217 11.00000 -1.20000 AFIX 0 C7 1 0.882980 0.693679 0.401853 11.00000 0.07332 0.08159 = 0.06899 0.00062 -0.00385 -0.03062 AFIX 43 H7 2 0.946459 0.686675 0.421865 11.00000 -1.20000 AFIX 0 C8 1 0.820318 0.634080 0.390116 11.00000 0.06668 0.05825 = 0.06273 0.00391 -0.00285 -0.01453 AFIX 43 H8 2 0.842030 0.587267 0.402452 11.00000 -1.20000 AFIX 0 C9 1 0.421413 0.677446 0.308511 11.00000 0.06502 0.04303 = 0.10027 0.00758 -0.00112 0.01248 AFIX 23 H9A 2 0.463976 0.710216 0.335306 11.00000 -1.20000 H9B 2 0.378785 0.707645 0.279237 11.00000 -1.20000 AFIX 0 C10 1 0.372595 0.634508 0.426188 11.00000 0.10708 0.06275 = 0.07081 -0.01224 -0.02164 0.01231 AFIX 43 H10 2 0.427939 0.660131 0.443818 11.00000 -1.20000 AFIX 0 C11 1 0.309504 0.595957 0.470225 11.00000 0.18316 0.07614 = 0.05317 -0.00470 0.00314 0.03126 AFIX 43 H11 2 0.322269 0.596123 0.517228 11.00000 -1.20000 AFIX 0 C12 1 0.228570 0.557691 0.444781 11.00000 0.13938 0.07080 = 0.09751 0.00125 0.05451 0.01796 AFIX 43 H12 2 0.186872 0.531125 0.474320 11.00000 -1.20000 AFIX 0 C13 1 0.208994 0.558475 0.376125 11.00000 0.06710 0.06938 = 0.11095 -0.00564 0.01685 0.00333 AFIX 43 H13 2 0.153310 0.533051 0.358734 11.00000 -1.20000 AFIX 0 C14 1 0.271380 0.596728 0.332755 11.00000 0.06033 0.06219 = 0.06438 -0.00108 -0.00472 0.01176 AFIX 43 H14 2 0.257515 0.596718 0.285895 11.00000 -1.20000 AFIX 0 C15 1 0.354313 0.635308 0.356761 11.00000 0.05868 0.04272 = 0.06114 -0.00390 -0.00730 0.01529 C16 1 0.464420 0.452582 0.292618 11.00000 0.03944 0.03708 = 0.05611 -0.00003 -0.00406 0.00147 AFIX 13 H16 2 0.407803 0.486654 0.285081 11.00000 -1.20000 AFIX 0 C17 1 0.426754 0.394678 0.343100 11.00000 0.03629 0.04239 = 0.05526 0.00009 0.00193 0.00257 C18 1 0.404758 0.414229 0.409900 11.00000 0.06494 0.05545 = 0.06245 -0.00871 0.01068 -0.00282 AFIX 43 H18 2 0.415188 0.462409 0.424192 11.00000 -1.20000 AFIX 0 C19 1 0.367590 0.363323 0.455610 11.00000 0.07389 0.08663 = 0.05720 0.00453 0.01236 -0.00806 AFIX 43 H19 2 0.353384 0.377405 0.500533 11.00000 -1.20000 AFIX 0 C20 1 0.351239 0.292143 0.435789 11.00000 0.05780 0.07407 = 0.08434 0.02511 0.00759 -0.00783 AFIX 43 H20 2 0.326686 0.257797 0.467044 11.00000 -1.20000 AFIX 0 C21 1 0.371427 0.272195 0.369557 11.00000 0.06040 0.04669 = 0.09455 0.00502 0.00542 -0.00988 AFIX 43 H21 2 0.359608 0.224116 0.355464 11.00000 -1.20000 AFIX 0 C22 1 0.409288 0.322885 0.323293 11.00000 0.05181 0.04367 = 0.06582 -0.00509 0.00417 -0.00481 AFIX 43 H22 2 0.423143 0.308531 0.278395 11.00000 -1.20000 AFIX 0 C23 1 0.496081 0.424677 0.222671 11.00000 0.05150 0.04197 = 0.05104 0.00340 -0.00066 -0.00420 C24 1 0.588910 0.391371 0.212492 11.00000 0.06191 0.06093 = 0.05944 -0.00195 0.00557 0.00548 AFIX 43 H24 2 0.633138 0.385892 0.249426 11.00000 -1.20000 AFIX 0 C25 1 0.617428 0.366082 0.148813 11.00000 0.09040 0.07772 = 0.07879 -0.00692 0.02759 0.00005 AFIX 43 H25 2 0.680553 0.343901 0.143010 11.00000 -1.20000 AFIX 0 C26 1 0.554266 0.373320 0.094809 11.00000 0.13998 0.10153 = 0.05941 -0.01033 0.01933 -0.01327 AFIX 43 H26 2 0.574039 0.356599 0.051674 11.00000 -1.20000 AFIX 0 C27 1 0.460999 0.405273 0.103399 11.00000 0.12858 0.13380 = 0.05970 -0.00292 -0.02838 -0.00715 AFIX 43 H27 2 0.416915 0.409322 0.066226 11.00000 -1.20000 AFIX 0 C28 1 0.431557 0.431943 0.167964 11.00000 0.07256 0.09042 = 0.06509 0.00072 -0.01486 0.00134 AFIX 43 H28 2 0.368596 0.454422 0.173573 11.00000 -1.20000 AFIX 0 N1 3 0.547622 0.495809 0.323509 11.00000 0.04533 0.03469 = 0.05155 0.00323 -0.00369 0.00144 N2 3 0.617592 0.463284 0.363225 11.00000 0.05179 0.03987 = 0.06509 0.00773 -0.01185 -0.00059 N3 3 0.685659 0.513269 0.379481 11.00000 0.05293 0.04234 = 0.06069 0.00530 -0.00798 -0.00528 S1 4 0.503060 0.621239 0.254111 11.00000 0.06493 0.05013 = 0.05791 0.01687 -0.00289 0.00522 HKLF 4 REM Pbca_a.res in Pbca REM R1 = 0.0520 for 3461 Fo > 4sig(Fo) and 0.0923 for all 5321 data REM 289 parameters refined using 0 restraints END WGHT 0.0457 1.1536 REM Highest difference peak 0.204, deepest hole -0.198, 1-sigma level 0.030 Q1 1 0.4619 0.6433 0.2896 11.00000 0.05 0.20 Q2 1 0.3863 0.3679 0.3253 11.00000 0.05 0.16 Q3 1 0.5936 0.5843 0.3544 11.00000 0.05 0.16 Q4 1 0.5178 0.5976 0.3000 11.00000 0.05 0.15 Q5 1 0.6931 0.6090 0.3517 11.00000 0.05 0.15 ; _shelx_res_checksum 19597 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, 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 C1 C 0.57123(13) 0.56806(9) 0.31248(9) 0.0429(4) Uani 1 1 d . . . . . C2 C 0.66034(14) 0.57851(9) 0.34929(9) 0.0446(4) Uani 1 1 d . . . . . C3 C 0.72547(14) 0.64313(10) 0.36018(9) 0.0484(4) Uani 1 1 d . . . . . C4 C 0.69665(18) 0.71347(11) 0.34245(14) 0.0756(7) Uani 1 1 d . . . . . H4 H 0.6337 0.7212 0.3219 0.091 Uiso 1 1 calc R U . . . C5 C 0.7600(2) 0.77269(12) 0.35487(16) 0.0879(8) Uani 1 1 d . . . . . H5 H 0.7388 0.8197 0.3429 0.106 Uiso 1 1 calc R U . . . C6 C 0.8521(2) 0.76324(13) 0.38413(13) 0.0762(7) Uani 1 1 d . . . . . H6 H 0.8941 0.8034 0.3922 0.091 Uiso 1 1 calc R U . . . C7 C 0.88298(19) 0.69368(14) 0.40185(12) 0.0746(7) Uani 1 1 d . . . . . H7 H 0.9465 0.6867 0.4219 0.090 Uiso 1 1 calc R U . . . C8 C 0.82032(17) 0.63408(12) 0.39012(11) 0.0626(6) Uani 1 1 d . . . . . H8 H 0.8420 0.5873 0.4025 0.075 Uiso 1 1 calc R U . . . C9 C 0.42141(16) 0.67745(11) 0.30851(13) 0.0694(6) Uani 1 1 d . . . . . H9A H 0.4640 0.7102 0.3353 0.083 Uiso 1 1 calc R U . . . H9B H 0.3788 0.7076 0.2792 0.083 Uiso 1 1 calc R U . . . C10 C 0.3726(2) 0.63451(13) 0.42619(13) 0.0802(7) Uani 1 1 d . . . . . H10 H 0.4279 0.6601 0.4438 0.096 Uiso 1 1 calc R U . . . C11 C 0.3095(3) 0.59596(16) 0.47022(14) 0.1042(11) Uani 1 1 d . . . . . H11 H 0.3223 0.5961 0.5172 0.125 Uiso 1 1 calc R U . . . C12 C 0.2286(3) 0.55769(16) 0.44478(18) 0.1026(10) Uani 1 1 d . . . . . H12 H 0.1869 0.5311 0.4743 0.123 Uiso 1 1 calc R U . . . C13 C 0.20899(19) 0.55847(14) 0.37612(16) 0.0825(7) Uani 1 1 d . . . . . H13 H 0.1533 0.5331 0.3587 0.099 Uiso 1 1 calc R U . . . C14 C 0.27138(16) 0.59673(12) 0.33276(12) 0.0623(5) Uani 1 1 d . . . . . H14 H 0.2575 0.5967 0.2859 0.075 Uiso 1 1 calc R U . . . C15 C 0.35431(15) 0.63531(10) 0.35676(11) 0.0542(5) Uani 1 1 d . . . . . C16 C 0.46442(13) 0.45258(9) 0.29262(9) 0.0442(4) Uani 1 1 d . . . . . H16 H 0.4078 0.4867 0.2851 0.053 Uiso 1 1 calc R U . . . C17 C 0.42675(13) 0.39468(9) 0.34310(10) 0.0446(4) Uani 1 1 d . . . . . C18 C 0.40476(16) 0.41423(12) 0.40990(11) 0.0609(5) Uani 1 1 d . . . . . H18 H 0.4152 0.4624 0.4242 0.073 Uiso 1 1 calc R U . . . C19 C 0.36759(17) 0.36332(14) 0.45561(12) 0.0726(6) Uani 1 1 d . . . . . H19 H 0.3534 0.3774 0.5005 0.087 Uiso 1 1 calc R U . . . C20 C 0.35124(16) 0.29214(13) 0.43579(13) 0.0721(6) Uani 1 1 d . . . . . H20 H 0.3267 0.2578 0.4670 0.086 Uiso 1 1 calc R U . . . C21 C 0.37143(16) 0.27219(11) 0.36956(13) 0.0672(6) Uani 1 1 d . . . . . H21 H 0.3596 0.2241 0.3555 0.081 Uiso 1 1 calc R U . . . C22 C 0.40929(14) 0.32289(10) 0.32329(11) 0.0538(5) Uani 1 1 d . . . . . H22 H 0.4231 0.3085 0.2784 0.065 Uiso 1 1 calc R U . . . C23 C 0.49608(14) 0.42468(9) 0.22267(10) 0.0482(4) Uani 1 1 d . . . . . C24 C 0.58891(16) 0.39137(11) 0.21249(11) 0.0608(5) Uani 1 1 d . . . . . H24 H 0.6331 0.3859 0.2494 0.073 Uiso 1 1 calc R U . . . C25 C 0.6174(2) 0.36608(13) 0.14881(14) 0.0823(7) Uani 1 1 d . . . . . H25 H 0.6806 0.3439 0.1430 0.099 Uiso 1 1 calc R U . . . C26 C 0.5543(3) 0.37332(17) 0.09481(14) 0.1003(9) Uani 1 1 d . . . . . H26 H 0.5740 0.3566 0.0517 0.120 Uiso 1 1 calc R U . . . C27 C 0.4610(3) 0.4053(2) 0.10340(14) 0.1074(10) Uani 1 1 d . . . . . H27 H 0.4169 0.4093 0.0662 0.129 Uiso 1 1 calc R U . . . C28 C 0.43156(18) 0.43194(14) 0.16796(12) 0.0760(7) Uani 1 1 d . . . . . H28 H 0.3686 0.4544 0.1736 0.091 Uiso 1 1 calc R U . . . N1 N 0.54762(11) 0.49581(7) 0.32351(7) 0.0439(3) Uani 1 1 d . . . . . N2 N 0.61759(12) 0.46328(8) 0.36323(8) 0.0522(4) Uani 1 1 d . . . . . N3 N 0.68566(12) 0.51327(8) 0.37948(8) 0.0520(4) Uani 1 1 d . . . . . S1 S 0.50306(4) 0.62124(3) 0.25411(3) 0.05766(16) 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 C1 0.0487(10) 0.0353(9) 0.0446(10) 0.0054(7) 0.0036(8) 0.0013(8) C2 0.0509(10) 0.0389(9) 0.0440(10) 0.0028(8) 0.0054(8) -0.0021(8) C3 0.0555(11) 0.0446(10) 0.0450(10) -0.0009(8) 0.0102(9) -0.0079(8) C4 0.0655(14) 0.0470(12) 0.114(2) 0.0119(12) -0.0007(13) -0.0081(10) C5 0.0804(18) 0.0443(12) 0.139(2) 0.0014(14) 0.0191(17) -0.0127(12) C6 0.0845(18) 0.0598(15) 0.0843(17) -0.0137(12) 0.0226(14) -0.0299(13) C7 0.0733(15) 0.0816(17) 0.0690(15) 0.0006(12) -0.0039(12) -0.0306(13) C8 0.0667(13) 0.0583(12) 0.0627(13) 0.0039(10) -0.0029(11) -0.0145(11) C9 0.0650(13) 0.0430(11) 0.1003(18) 0.0076(11) -0.0011(13) 0.0125(10) C10 0.1071(19) 0.0627(14) 0.0708(16) -0.0122(12) -0.0216(15) 0.0123(14) C11 0.183(3) 0.0761(18) 0.0532(15) -0.0047(14) 0.003(2) 0.031(2) C12 0.139(3) 0.0708(18) 0.098(2) 0.0012(16) 0.055(2) 0.0180(18) C13 0.0671(15) 0.0694(16) 0.111(2) -0.0056(15) 0.0168(15) 0.0033(13) C14 0.0603(13) 0.0622(13) 0.0644(13) -0.0011(11) -0.0047(11) 0.0118(11) C15 0.0587(12) 0.0427(10) 0.0611(12) -0.0039(9) -0.0073(10) 0.0153(9) C16 0.0394(9) 0.0371(9) 0.0561(11) 0.0000(8) -0.0041(8) 0.0015(8) C17 0.0363(9) 0.0424(10) 0.0553(11) 0.0001(8) 0.0019(8) 0.0026(7) C18 0.0649(13) 0.0554(12) 0.0625(13) -0.0087(10) 0.0107(11) -0.0028(10) C19 0.0739(15) 0.0866(17) 0.0572(13) 0.0045(12) 0.0124(11) -0.0081(13) C20 0.0578(13) 0.0741(16) 0.0843(17) 0.0251(13) 0.0076(12) -0.0078(12) C21 0.0604(13) 0.0467(11) 0.0946(18) 0.0050(11) 0.0054(13) -0.0099(10) C22 0.0518(11) 0.0437(10) 0.0658(13) -0.0051(9) 0.0042(10) -0.0048(9) C23 0.0515(10) 0.0420(9) 0.0510(10) 0.0034(8) -0.0007(9) -0.0042(9) C24 0.0619(13) 0.0609(13) 0.0594(13) -0.0019(10) 0.0056(11) 0.0055(10) C25 0.0904(18) 0.0777(16) 0.0788(18) -0.0069(14) 0.0276(15) 0.0001(14) C26 0.140(3) 0.102(2) 0.0594(17) -0.0103(15) 0.0193(19) -0.013(2) C27 0.129(3) 0.134(3) 0.0597(17) -0.0029(17) -0.0284(18) -0.007(2) C28 0.0726(15) 0.0904(17) 0.0651(15) 0.0007(13) -0.0149(12) 0.0013(13) N1 0.0453(8) 0.0347(7) 0.0516(8) 0.0032(6) -0.0037(7) 0.0014(6) N2 0.0518(9) 0.0399(8) 0.0651(10) 0.0077(7) -0.0119(8) -0.0006(7) N3 0.0529(9) 0.0423(8) 0.0607(10) 0.0053(7) -0.0080(8) -0.0053(7) S1 0.0649(3) 0.0501(3) 0.0579(3) 0.0169(2) -0.0029(3) 0.0052(2) 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 N1 C1 C2 104.04(14) . . ? N1 C1 S1 121.33(13) . . ? C2 C1 S1 134.11(13) . . ? N3 C2 C1 108.01(15) . . ? N3 C2 C3 119.42(16) . . ? C1 C2 C3 132.58(16) . . ? C4 C3 C8 117.56(18) . . ? C4 C3 C2 123.12(19) . . ? C8 C3 C2 119.32(17) . . ? C3 C4 C5 120.9(2) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? C6 C5 C4 121.0(2) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C7 119.3(2) . . ? C5 C6 H6 120.4 . . ? C7 C6 H6 120.4 . . ? C6 C7 C8 120.4(2) . . ? C6 C7 H7 119.8 . . ? C8 C7 H7 119.8 . . ? C7 C8 C3 120.9(2) . . ? C7 C8 H8 119.6 . . ? C3 C8 H8 119.6 . . ? C15 C9 S1 115.06(14) . . ? C15 C9 H9A 108.5 . . ? S1 C9 H9A 108.5 . . ? C15 C9 H9B 108.5 . . ? S1 C9 H9B 108.5 . . ? H9A C9 H9B 107.5 . . ? C15 C10 C11 120.7(3) . . ? C15 C10 H10 119.7 . . ? C11 C10 H10 119.7 . . ? C12 C11 C10 120.1(3) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C13 C12 C11 119.9(3) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C12 C13 C14 119.9(3) . . ? C12 C13 H13 120.1 . . ? C14 C13 H13 120.1 . . ? C13 C14 C15 121.7(2) . . ? C13 C14 H14 119.2 . . ? C15 C14 H14 119.2 . . ? C10 C15 C14 117.8(2) . . ? C10 C15 C9 121.3(2) . . ? C14 C15 C9 120.9(2) . . ? N1 C16 C23 109.98(14) . . ? N1 C16 C17 110.31(14) . . ? C23 C16 C17 115.98(14) . . ? N1 C16 H16 106.7 . . ? C23 C16 H16 106.7 . . ? C17 C16 H16 106.7 . . ? C18 C17 C22 118.19(18) . . ? C18 C17 C16 119.86(16) . . ? C22 C17 C16 121.89(17) . . ? C19 C18 C17 120.7(2) . . ? C19 C18 H18 119.6 . . ? C17 C18 H18 119.6 . . ? C20 C19 C18 120.8(2) . . ? C20 C19 H19 119.6 . . ? C18 C19 H19 119.6 . . ? C21 C20 C19 119.2(2) . . ? C21 C20 H20 120.4 . . ? C19 C20 H20 120.4 . . ? C20 C21 C22 120.5(2) . . ? C20 C21 H21 119.7 . . ? C22 C21 H21 119.7 . . ? C17 C22 C21 120.6(2) . . ? C17 C22 H22 119.7 . . ? C21 C22 H22 119.7 . . ? C28 C23 C24 118.7(2) . . ? C28 C23 C16 119.84(18) . . ? C24 C23 C16 121.44(17) . . ? C25 C24 C23 121.3(2) . . ? C25 C24 H24 119.4 . . ? C23 C24 H24 119.4 . . ? C26 C25 C24 120.2(3) . . ? C26 C25 H25 119.9 . . ? C24 C25 H25 119.9 . . ? C25 C26 C27 120.0(3) . . ? C25 C26 H26 120.0 . . ? C27 C26 H26 120.0 . . ? C26 C27 C28 120.3(3) . . ? C26 C27 H27 119.8 . . ? C28 C27 H27 119.8 . . ? C23 C28 C27 119.5(2) . . ? C23 C28 H28 120.2 . . ? C27 C28 H28 120.2 . . ? N2 N1 C1 111.06(14) . . ? N2 N1 C16 120.59(13) . . ? C1 N1 C16 128.08(14) . . ? N3 N2 N1 107.51(13) . . ? N2 N3 C2 109.38(14) . . ? C1 S1 C9 103.68(10) . . ? 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 C1 N1 1.368(2) . ? C1 C2 1.387(2) . ? C1 S1 1.7409(17) . ? C2 N3 1.366(2) . ? C2 C3 1.470(2) . ? C3 C4 1.379(3) . ? C3 C8 1.387(3) . ? C4 C5 1.384(3) . ? C4 H4 0.9300 . ? C5 C6 1.349(4) . ? C5 H5 0.9300 . ? C6 C7 1.374(3) . ? C6 H6 0.9300 . ? C7 C8 1.381(3) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 C15 1.499(3) . ? C9 S1 1.822(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C15 1.372(3) . ? C10 C11 1.384(4) . ? C10 H10 0.9300 . ? C11 C12 1.365(4) . ? C11 H11 0.9300 . ? C12 C13 1.361(4) . ? C12 H12 0.9300 . ? C13 C14 1.368(3) . ? C13 H13 0.9300 . ? C14 C15 1.379(3) . ? C14 H14 0.9300 . ? C16 N1 1.476(2) . ? C16 C23 1.511(3) . ? C16 C17 1.523(2) . ? C16 H16 0.9800 . ? C17 C18 1.378(3) . ? C17 C22 1.381(2) . ? C18 C19 1.374(3) . ? C18 H18 0.9300 . ? C19 C20 1.369(3) . ? C19 H19 0.9300 . ? C20 C21 1.365(3) . ? C20 H20 0.9300 . ? C21 C22 1.382(3) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 C28 1.368(3) . ? C23 C24 1.377(3) . ? C24 C25 1.374(3) . ? C24 H24 0.9300 . ? C25 C26 1.346(4) . ? C25 H25 0.9300 . ? C26 C27 1.368(4) . ? C26 H26 0.9300 . ? C27 C28 1.402(4) . ? C27 H27 0.9300 . ? C28 H28 0.9300 . ? N1 N2 1.340(2) . ? N2 N3 1.315(2) . ?