#------------------------------------------------------------------------------ #$Date: 2014-01-12 07:35:53 +0000 (Sun, 12 Jan 2014) $ #$Revision: 92032 $ #$URL: svn://www.crystallography.net/cod/cif/2/23/88/2238834.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2238834 loop_ _publ_author_name 'Vr\'abel, Viktor' 'Siv\'y, J\'ulius' '\S)-1,5,11,11a-Tetrahydro-1-benzothieno[3,2-f]indolizin-3(2H)-one ; _journal_coeditor_code BQ2390 _journal_issue 12 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1819 _journal_page_last o1820 _journal_paper_doi 10.1107/S1600536813031693 _journal_volume 69 _journal_year 2013 _chemical_formula_iupac 'C14 H13 N O S' _chemical_formula_moiety 'C14 H13 N O S' _chemical_formula_sum 'C14 H13 N O S' _chemical_formula_weight 243.31 _chemical_name_systematic (11aS)-1,5,11,11a-Tetrahydro-1-benzothieno[3,2-f]indolizin-3(2H)-one _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 105.469(8) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 9.3327(8) _cell_length_b 12.4575(7) _cell_length_c 10.3103(7) _cell_measurement_reflns_used 3929 _cell_measurement_temperature 295(2) _cell_measurement_theta_max 24.554 _cell_measurement_theta_min 3.846 _cell_volume 1155.27(15) _computing_cell_refinement 'CrysAlis CCD (Oxford Diffraction, 2009)' _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, 2009)' _computing_data_reduction 'CrysAlis RED (Oxford Diffraction, 2009)' _computing_molecular_graphics ; PLATON (Spek, 2009), WinGX (Farrugia, 2012) and DIAMOND (Brandenburg, 2001) ; _computing_publication_material ; SHELXL97 (Sheldrick, 2008) ; _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 295(2) _diffrn_detector_area_resol_mean 10.4340 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur (Ruby, Gemini)' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0933 _diffrn_reflns_av_sigmaI/netI 0.0835 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 17520 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.01 _diffrn_reflns_theta_min 3.81 _exptl_absorpt_coefficient_mu 0.261 _exptl_absorpt_correction_T_max 0.969 _exptl_absorpt_correction_T_min 0.942 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; (CrysAlis RED; Oxford Diffraction, 2009) ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.399 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 512 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.191 _refine_diff_density_min -0.157 _refine_ls_abs_structure_details 'Flack (1983), 1923 Friedel pairs' _refine_ls_abs_structure_Flack -0.07(6) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.944 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 307 _refine_ls_number_reflns 4061 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 0.944 _refine_ls_R_factor_all 0.0735 _refine_ls_R_factor_gt 0.0395 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0158P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0581 _refine_ls_wR_factor_ref 0.0645 _reflns_number_gt 2918 _reflns_number_total 4061 _reflns_threshold_expression I>2sigma(I) _iucr_refine_instructions_details ; TITL P21a dve vzor. jednotky C14 H 13 N O S CELL 0.71073 9.33270 12.45750 10.31030 90.00000 105.46900 90.00000 ZERR 4 0.00080 0.00070 0.00070 0.00000 0.00800 0.00000 LATT -1 SYMM -X, Y+ 0.50000, -Z SFAC C H N O S UNIT 56 52 4 4 4 L.S. 9 FMAP 2 MERG 2 EQIV $1 1-X, 1/2+Y, 2-Z HTAB HTAB C20 O2_$1 PLAN -10 ACTA 50 BOND $H SHEL 6.0 0.84 CONF WGHT 0.015800 FVAR 1.78014 C9 1 1.154518 0.506346 1.007046 11.00000 0.04435 0.05056 = 0.05540 -0.01235 0.00870 -0.00317 AFIX 43 H9 2 1.192976 0.575095 1.005816 11.00000 -1.20000 AFIX 0 C10 1 1.210494 0.439553 1.112871 11.00000 0.04341 0.07416 = 0.04859 -0.01142 0.00144 -0.00142 AFIX 43 H10 2 1.286518 0.463155 1.185301 11.00000 -1.20000 AFIX 0 C11 1 1.154528 0.336256 1.113137 11.00000 0.04840 0.07115 = 0.04167 0.00633 0.00592 0.00149 AFIX 43 H11 2 1.195052 0.290676 1.184996 11.00000 -1.20000 AFIX 0 C12 1 1.039909 0.300574 1.008416 11.00000 0.04928 0.05415 = 0.04684 0.00419 0.00809 -0.00692 AFIX 43 H12 2 1.003019 0.231427 1.010481 11.00000 -1.20000 AFIX 0 C15 1 0.771992 0.247244 0.752728 11.00000 0.04815 0.04499 = 0.04929 0.00267 0.00358 0.00145 AFIX 23 H15B 2 0.836203 0.189516 0.739109 11.00000 -1.20000 H15A 2 0.733921 0.228429 0.828574 11.00000 -1.20000 AFIX 0 C2 1 0.527712 0.194816 0.604882 11.00000 0.03625 0.04301 = 0.05722 -0.00957 0.00981 0.00691 C3 1 0.436975 0.221536 0.464697 11.00000 0.03885 0.05943 = 0.04951 -0.00993 0.00524 0.00490 AFIX 23 H3B 2 0.335016 0.237358 0.464039 11.00000 -1.20000 H3A 2 0.437150 0.161939 0.404192 11.00000 -1.20000 AFIX 0 C4 1 0.510103 0.319150 0.422434 11.00000 0.05243 0.06147 = 0.04730 -0.00162 0.00155 0.00209 AFIX 23 H4B 2 0.453019 0.383419 0.427119 11.00000 -1.20000 H4A 2 0.518298 0.310939 0.331130 11.00000 -1.20000 AFIX 0 C6 1 0.711075 0.438492 0.569227 11.00000 0.05531 0.04168 = 0.04270 0.00232 0.00381 0.00165 AFIX 23 H6B 2 0.747591 0.475695 0.501782 11.00000 -1.20000 H6A 2 0.626623 0.478067 0.582553 11.00000 -1.20000 AFIX 0 C8 1 1.039168 0.470414 0.900918 11.00000 0.04044 0.04016 = 0.04135 -0.00311 0.01344 0.00044 C13 1 0.979062 0.366890 0.899934 11.00000 0.03585 0.04184 = 0.03872 -0.00034 0.01117 0.00042 C7 1 0.830865 0.433239 0.698593 11.00000 0.04277 0.03711 = 0.04285 -0.00214 0.01101 0.00195 C14 1 0.859290 0.348917 0.782736 11.00000 0.04286 0.03477 = 0.03838 0.00077 0.00785 -0.00121 C5 1 0.663427 0.325730 0.521385 11.00000 0.04368 0.04547 = 0.03969 -0.00175 0.00402 0.00637 AFIX 13 H5 2 0.737271 0.293952 0.480816 11.00000 -1.20000 AFIX 0 C23 1 0.075480 0.396255 0.437075 11.00000 0.03498 0.05513 = 0.03926 0.00191 -0.00437 0.00617 AFIX 43 H23 2 0.045870 0.445712 0.367491 11.00000 -1.20000 AFIX 0 C24 1 0.012757 0.296655 0.426327 11.00000 0.03482 0.06358 = 0.04259 -0.00932 -0.00006 -0.00373 AFIX 43 H24 2 -0.058955 0.277584 0.348257 11.00000 -1.20000 AFIX 0 C25 1 0.055272 0.223627 0.531127 11.00000 0.03893 0.05169 = 0.05284 -0.00695 0.00673 -0.00798 AFIX 43 H25 2 0.010940 0.156213 0.522839 11.00000 -1.20000 AFIX 0 C26 1 0.162232 0.249535 0.647316 11.00000 0.04402 0.04365 = 0.04004 0.00212 0.00386 -0.00265 AFIX 43 H26 2 0.189110 0.200265 0.717385 11.00000 -1.20000 AFIX 0 C29 1 0.425994 0.331086 0.889601 11.00000 0.04144 0.04120 = 0.03747 0.00073 0.00080 -0.00233 AFIX 23 H29B 2 0.355787 0.315733 0.941613 11.00000 -1.20000 H29A 2 0.462741 0.263366 0.864881 11.00000 -1.20000 AFIX 0 C16 1 0.660878 0.350674 1.063783 11.00000 0.04651 0.05367 = 0.04345 0.00576 0.00246 -0.00109 C17 1 0.755279 0.440091 1.137755 11.00000 0.04926 0.06524 = 0.04803 -0.00542 -0.00489 -0.00356 AFIX 23 H17B 2 0.746503 0.445145 1.229205 11.00000 -1.20000 H17A 2 0.858887 0.428662 1.140620 11.00000 -1.20000 AFIX 0 C18 1 0.697672 0.539323 1.060633 11.00000 0.06420 0.05280 = 0.07552 -0.01140 -0.02795 -0.00921 AFIX 23 H18B 2 0.762340 0.561089 1.005699 11.00000 -1.20000 H18A 2 0.691503 0.597575 1.121339 11.00000 -1.20000 AFIX 0 C20 1 0.509395 0.556167 0.831663 11.00000 0.04310 0.03577 = 0.04825 -0.00038 0.00427 -0.00137 AFIX 23 H20B 2 0.479017 0.630589 0.832271 11.00000 -1.20000 H20A 2 0.597438 0.553333 0.798699 11.00000 -1.20000 AFIX 0 C22 1 0.183517 0.422586 0.552692 11.00000 0.02998 0.04101 = 0.03785 -0.00150 0.00768 0.00393 C27 1 0.229650 0.349795 0.659056 11.00000 0.02711 0.03872 = 0.03412 -0.00194 0.00559 0.00196 C21 1 0.387170 0.491959 0.741442 11.00000 0.03269 0.04185 = 0.03628 -0.00055 0.00643 0.00316 C28 1 0.349875 0.392024 0.765378 11.00000 0.02855 0.03623 = 0.03466 0.00016 0.00483 0.00416 C19 1 0.544046 0.510789 0.972600 11.00000 0.04849 0.04629 = 0.04142 -0.01275 0.00595 0.00170 AFIX 13 H19 2 0.468315 0.534323 1.016454 11.00000 -1.20000 AFIX 0 N1 3 0.648928 0.259734 0.632886 11.00000 0.04021 0.04258 = 0.03991 0.00311 0.00135 -0.00102 N2 3 0.548704 0.393599 0.970023 11.00000 0.04259 0.03766 = 0.03712 0.00063 -0.00985 -0.00065 O1 4 0.502628 0.126367 0.679681 11.00000 0.06057 0.05578 = 0.06601 0.00434 0.01430 -0.01279 O2 4 0.682781 0.254535 1.083029 11.00000 0.06642 0.05418 = 0.07282 0.01963 -0.01357 -0.00121 S1 5 0.948284 0.541483 0.757814 11.00000 0.05720 0.03743 = 0.05342 0.00046 0.01064 -0.00456 S2 5 0.282095 0.541896 0.588045 11.00000 0.04441 0.04185 = 0.04929 0.00957 0.00011 0.00047 HKLF 4 REM P21a dve vzor. jednotky C14 H 13 N O S REM R1 = 0.0395 for 2918 Fo > 4sig(Fo) and 0.0735 for all 4061 data REM 307 parameters refined using 1 restraints END ; _[local]_cod_data_source_file bq2390.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21' _cod_original_cell_volume 1155.27(14) _cod_database_code 2238834 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_symmetry_multiplicity C C9 1.1545(4) 0.5063(2) 1.0070(3) 0.0510(9) Uani d . 1 1 H H9 1.1930 0.5751 1.0058 0.061 Uiso calc R 1 1 C C10 1.2105(4) 0.4396(3) 1.1129(3) 0.0575(9) Uani d . 1 1 H H10 1.2865 0.4632 1.1853 0.069 Uiso calc R 1 1 C C11 1.1545(4) 0.3363(3) 1.1131(3) 0.0549(9) Uani d . 1 1 H H11 1.1951 0.2907 1.1850 0.066 Uiso calc R 1 1 C C12 1.0399(3) 0.3006(2) 1.0084(3) 0.0510(8) Uani d . 1 1 H H12 1.0030 0.2314 1.0105 0.061 Uiso calc R 1 1 C C15 0.7720(3) 0.2472(2) 0.7527(3) 0.0493(8) Uani d . 1 1 H H15B 0.8362 0.1895 0.7391 0.059 Uiso calc R 1 1 H H15A 0.7339 0.2284 0.8286 0.059 Uiso calc R 1 1 C C2 0.5277(4) 0.1948(2) 0.6049(3) 0.0460(8) Uani d . 1 1 C C3 0.4370(3) 0.2215(2) 0.4647(3) 0.0505(8) Uani d . 1 1 H H3B 0.3350 0.2374 0.4640 0.061 Uiso calc R 1 1 H H3A 0.4372 0.1619 0.4042 0.061 Uiso calc R 1 1 C C4 0.5101(4) 0.3191(2) 0.4224(3) 0.0560(9) Uani d . 1 1 H H4B 0.4530 0.3834 0.4271 0.067 Uiso calc R 1 1 H H4A 0.5183 0.3109 0.3311 0.067 Uiso calc R 1 1 C C6 0.7111(3) 0.4385(2) 0.5692(3) 0.0483(8) Uani d . 1 1 H H6B 0.7476 0.4757 0.5018 0.058 Uiso calc R 1 1 H H6A 0.6266 0.4781 0.5826 0.058 Uiso calc R 1 1 C C8 1.0392(3) 0.4704(2) 0.9009(3) 0.0402(7) Uani d . 1 1 C C13 0.9791(3) 0.36689(19) 0.8999(3) 0.0386(7) Uani d . 1 1 C C7 0.8309(3) 0.43324(19) 0.6986(3) 0.0410(7) Uani d . 1 1 C C14 0.8593(3) 0.3489(2) 0.7827(3) 0.0392(7) Uani d . 1 1 C C5 0.6634(3) 0.3257(2) 0.5214(3) 0.0443(8) Uani d . 1 1 H H5 0.7373 0.2940 0.4808 0.053 Uiso calc R 1 1 C C23 0.0755(3) 0.3963(2) 0.4371(3) 0.0459(8) Uani d . 1 1 H H23 0.0459 0.4457 0.3675 0.055 Uiso calc R 1 1 C C24 0.0128(3) 0.2967(2) 0.4263(3) 0.0490(8) Uani d . 1 1 H H24 -0.0590 0.2776 0.3483 0.059 Uiso calc R 1 1 C C25 0.0553(3) 0.2236(2) 0.5311(3) 0.0489(8) Uani d . 1 1 H H25 0.0109 0.1562 0.5228 0.059 Uiso calc R 1 1 C C26 0.1622(3) 0.2495(2) 0.6473(3) 0.0440(8) Uani d . 1 1 H H26 0.1891 0.2003 0.7174 0.053 Uiso calc R 1 1 C C29 0.4260(3) 0.3311(2) 0.8896(3) 0.0419(7) Uani d . 1 1 H H29B 0.3558 0.3157 0.9416 0.050 Uiso calc R 1 1 H H29A 0.4627 0.2634 0.8649 0.050 Uiso calc R 1 1 C C16 0.6609(4) 0.3507(2) 1.0638(3) 0.0497(8) Uani d . 1 1 C C17 0.7553(4) 0.4401(2) 1.1378(3) 0.0576(9) Uani d . 1 1 H H17B 0.7465 0.4451 1.2292 0.069 Uiso calc R 1 1 H H17A 0.8589 0.4287 1.1406 0.069 Uiso calc R 1 1 C C18 0.6977(4) 0.5393(3) 1.0606(3) 0.0731(10) Uani d . 1 1 H H18B 0.7623 0.5611 1.0057 0.088 Uiso calc R 1 1 H H18A 0.6915 0.5976 1.1213 0.088 Uiso calc R 1 1 C C20 0.5094(3) 0.5562(2) 0.8317(3) 0.0439(7) Uani d . 1 1 H H20B 0.4790 0.6306 0.8323 0.053 Uiso calc R 1 1 H H20A 0.5974 0.5533 0.7987 0.053 Uiso calc R 1 1 C C22 0.1835(3) 0.42259(19) 0.5527(3) 0.0365(7) Uani d . 1 1 C C27 0.2297(3) 0.3498(2) 0.6591(2) 0.0338(7) Uani d . 1 1 C C21 0.3872(3) 0.4920(2) 0.7414(3) 0.0375(7) Uani d . 1 1 C C28 0.3499(3) 0.3920(2) 0.7654(2) 0.0338(6) Uani d . 1 1 C C19 0.5440(4) 0.51079(19) 0.9726(3) 0.0466(8) Uani d . 1 1 H H19 0.4683 0.5343 1.0165 0.056 Uiso calc R 1 1 N N1 0.6489(3) 0.25973(16) 0.6329(2) 0.0427(6) Uani d . 1 1 N N2 0.5487(3) 0.39360(16) 0.9700(2) 0.0430(6) Uani d . 1 1 O O1 0.5026(3) 0.12637(15) 0.6797(2) 0.0613(6) Uani d . 1 1 O O2 0.6828(3) 0.25454(16) 1.0830(2) 0.0706(7) Uani d . 1 1 S S1 0.94828(9) 0.54148(6) 0.75781(7) 0.0501(2) Uani d . 1 1 S S2 0.28209(8) 0.54190(6) 0.58804(7) 0.0476(2) Uani d . 1 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C9 0.044(2) 0.0506(19) 0.055(2) -0.0032(15) 0.0087(18) -0.0123(14) C10 0.043(2) 0.074(2) 0.049(2) -0.0014(19) 0.0014(16) -0.0114(17) C11 0.048(2) 0.071(2) 0.042(2) 0.0015(18) 0.0059(17) 0.0063(15) C12 0.049(2) 0.0541(18) 0.0468(19) -0.0069(16) 0.0081(18) 0.0042(14) C15 0.048(2) 0.0450(17) 0.049(2) 0.0015(15) 0.0036(17) 0.0027(13) C2 0.036(2) 0.0430(18) 0.057(2) 0.0069(15) 0.0098(17) -0.0096(16) C3 0.039(2) 0.0594(19) 0.050(2) 0.0049(16) 0.0052(16) -0.0099(15) C4 0.052(2) 0.061(2) 0.047(2) 0.0021(17) 0.0016(17) -0.0016(15) C6 0.055(2) 0.0417(16) 0.0427(18) 0.0017(15) 0.0038(16) 0.0023(13) C8 0.040(2) 0.0402(17) 0.0414(18) 0.0004(14) 0.0134(16) -0.0031(12) C13 0.0358(19) 0.0418(17) 0.0387(17) 0.0004(13) 0.0112(15) -0.0003(13) C7 0.043(2) 0.0371(16) 0.0429(18) 0.0020(13) 0.0110(15) -0.0021(13) C14 0.043(2) 0.0348(15) 0.0384(17) -0.0012(13) 0.0079(15) 0.0008(12) C5 0.044(2) 0.0455(17) 0.0397(18) 0.0064(14) 0.0040(15) -0.0017(13) C23 0.035(2) 0.0551(19) 0.0393(18) 0.0062(15) -0.0044(15) 0.0019(14) C24 0.0348(19) 0.064(2) 0.0426(19) -0.0037(16) -0.0001(15) -0.0093(15) C25 0.039(2) 0.0517(18) 0.053(2) -0.0080(15) 0.0067(17) -0.0070(15) C26 0.044(2) 0.0436(17) 0.0400(18) -0.0026(14) 0.0039(15) 0.0021(13) C29 0.041(2) 0.0412(16) 0.0375(17) -0.0023(14) 0.0008(15) 0.0007(13) C16 0.047(2) 0.054(2) 0.043(2) -0.0011(16) 0.0025(17) 0.0058(15) C17 0.049(2) 0.065(2) 0.048(2) -0.0036(18) -0.0049(16) -0.0054(16) C18 0.064(2) 0.0528(18) 0.076(2) -0.009(2) -0.0280(19) -0.011(2) C20 0.0431(19) 0.0358(15) 0.0482(17) -0.0014(14) 0.0043(15) -0.0004(14) C22 0.0300(18) 0.0410(16) 0.0378(17) 0.0039(13) 0.0077(14) -0.0015(13) C27 0.0271(17) 0.0387(15) 0.0341(16) 0.0020(12) 0.0056(13) -0.0019(12) C21 0.0327(18) 0.0419(15) 0.0363(17) 0.0032(13) 0.0064(15) -0.0005(12) C28 0.0286(17) 0.0362(15) 0.0347(16) 0.0042(12) 0.0048(14) 0.0002(12) C19 0.048(2) 0.046(2) 0.0414(18) 0.0017(14) 0.0059(16) -0.0128(12) N1 0.0402(16) 0.0426(13) 0.0399(15) -0.0010(12) 0.0013(13) 0.0031(10) N2 0.0426(17) 0.0377(13) 0.0371(14) -0.0006(11) -0.0098(13) 0.0006(11) O1 0.0606(16) 0.0558(13) 0.0660(16) -0.0128(12) 0.0143(12) 0.0043(11) O2 0.0664(18) 0.0542(14) 0.0728(16) -0.0012(12) -0.0136(13) 0.0196(11) S1 0.0572(6) 0.0374(4) 0.0534(5) -0.0046(4) 0.0106(4) 0.0005(4) S2 0.0444(5) 0.0419(4) 0.0493(4) 0.0005(4) 0.0001(4) 0.0096(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 C10 C9 C8 119.1(3) C10 C9 H9 120.5 C8 C9 H9 120.5 C9 C10 C11 120.3(3) C9 C10 H10 119.9 C11 C10 H10 119.9 C12 C11 C10 120.8(3) C12 C11 H11 119.6 C10 C11 H11 119.6 C11 C12 C13 120.5(3) C11 C12 H12 119.8 C13 C12 H12 119.8 N1 C15 C14 110.4(2) N1 C15 H15B 109.6 C14 C15 H15B 109.6 N1 C15 H15A 109.6 C14 C15 H15A 109.6 H15B C15 H15A 108.1 O1 C2 N1 125.1(3) O1 C2 C3 127.7(3) N1 C2 C3 107.2(3) C2 C3 C4 105.8(3) C2 C3 H3B 110.6 C4 C3 H3B 110.6 C2 C3 H3A 110.6 C4 C3 H3A 110.6 H3B C3 H3A 108.7 C3 C4 C5 105.4(2) C3 C4 H4B 110.7 C5 C4 H4B 110.7 C3 C4 H4A 110.7 C5 C4 H4A 110.7 H4B C4 H4A 108.8 C7 C6 C5 109.5(2) C7 C6 H6B 109.8 C5 C6 H6B 109.8 C7 C6 H6A 109.8 C5 C6 H6A 109.8 H6B C6 H6A 108.2 C9 C8 C13 121.7(3) C9 C8 S1 127.3(2) C13 C8 S1 111.0(2) C12 C13 C8 117.7(2) C12 C13 C14 130.5(2) C8 C13 C14 111.8(2) C14 C7 C6 125.6(2) C14 C7 S1 112.4(2) C6 C7 S1 121.96(19) C7 C14 C13 113.5(2) C7 C14 C15 121.8(2) C13 C14 C15 124.7(2) N1 C5 C6 110.4(2) N1 C5 C4 103.4(2) C6 C5 C4 114.2(2) N1 C5 H5 109.5 C6 C5 H5 109.5 C4 C5 H5 109.5 C24 C23 C22 119.0(3) C24 C23 H23 120.5 C22 C23 H23 120.5 C23 C24 C25 120.4(3) C23 C24 H24 119.8 C25 C24 H24 119.8 C26 C25 C24 120.9(3) C26 C25 H25 119.5 C24 C25 H25 119.5 C25 C26 C27 119.5(3) C25 C26 H26 120.2 C27 C26 H26 120.2 N2 C29 C28 109.9(2) N2 C29 H29B 109.7 C28 C29 H29B 109.7 N2 C29 H29A 109.7 C28 C29 H29A 109.7 H29B C29 H29A 108.2 O2 C16 N2 125.2(3) O2 C16 C17 126.6(3) N2 C16 C17 108.2(2) C18 C17 C16 105.4(2) C18 C17 H17B 110.7 C16 C17 H17B 110.7 C18 C17 H17A 110.7 C16 C17 H17A 110.7 H17B C17 H17A 108.8 C17 C18 C19 105.8(3) C17 C18 H18B 110.6 C19 C18 H18B 110.6 C17 C18 H18A 110.6 C19 C18 H18A 110.6 H18B C18 H18A 108.7 C21 C20 C19 109.3(2) C21 C20 H20B 109.8 C19 C20 H20B 109.8 C21 C20 H20A 109.8 C19 C20 H20A 109.8 H20B C20 H20A 108.3 C23 C22 C27 121.6(2) C23 C22 S2 127.6(2) C27 C22 S2 110.82(19) C26 C27 C22 118.5(2) C26 C27 C28 129.5(2) C22 C27 C28 111.9(2) C28 C21 C20 125.3(3) C28 C21 S2 113.0(2) C20 C21 S2 121.7(2) C21 C28 C27 112.9(2) C21 C28 C29 123.0(3) C27 C28 C29 124.1(2) N2 C19 C20 110.9(2) N2 C19 C18 102.5(3) C20 C19 C18 114.4(3) N2 C19 H19 109.6 C20 C19 H19 109.6 C18 C19 H19 109.6 C2 N1 C5 114.7(2) C2 N1 C15 122.8(2) C5 N1 C15 121.0(2) C16 N2 C29 123.2(2) C16 N2 C19 114.1(2) C29 N2 C19 121.6(2) C8 S1 C7 91.27(13) C22 S2 C21 91.34(13) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C9 C10 1.361(4) C9 C8 1.389(4) C9 H9 0.9300 C10 C11 1.389(4) C10 H10 0.9300 C11 C12 1.375(4) C11 H11 0.9300 C12 C13 1.385(4) C12 H12 0.9300 C15 N1 1.454(3) C15 C14 1.493(4) C15 H15B 0.9700 C15 H15A 0.9700 C2 O1 1.214(3) C2 N1 1.358(4) C2 C3 1.505(4) C3 C4 1.514(4) C3 H3B 0.9700 C3 H3A 0.9700 C4 C5 1.522(4) C4 H4B 0.9700 C4 H4A 0.9700 C6 C7 1.496(4) C6 C5 1.516(3) C6 H6B 0.9700 C6 H6A 0.9700 C8 C13 1.405(3) C8 S1 1.736(3) C13 C14 1.428(4) C7 C14 1.343(3) C7 S1 1.742(3) C5 N1 1.449(3) C5 H5 0.9800 C23 C24 1.364(4) C23 C22 1.380(3) C23 H23 0.9300 C24 C25 1.387(4) C24 H24 0.9300 C25 C26 1.378(4) C25 H25 0.9300 C26 C27 1.389(3) C26 H26 0.9300 C29 N2 1.449(3) C29 C28 1.495(3) C29 H29B 0.9700 C29 H29A 0.9700 C16 O2 1.222(3) C16 N2 1.333(3) C16 C17 1.497(4) C17 C18 1.490(4) C17 H17B 0.9700 C17 H17A 0.9700 C18 C19 1.520(4) C18 H18B 0.9700 C18 H18A 0.9700 C20 C21 1.497(4) C20 C19 1.512(3) C20 H20B 0.9700 C20 H20A 0.9700 C22 C27 1.399(3) C22 S2 1.735(3) C27 C28 1.443(4) C21 C28 1.333(3) C21 S2 1.739(3) C19 N2 1.461(3) C19 H19 0.9800 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA C20 H20B O2 2_657 0.97 2.48 3.307(4) 143.6 C3 H3B Cg14 1_555 0.97 2.59 3.502(3) 157.0 C17 H17A Cg4 1_555 0.97 2.92 3.800(4) 151.0 C29 H29B Cg4 1_455 0.97 2.90 3.706(3) 142.0 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 C8 C9 C10 C11 1.2(5) C9 C10 C11 C12 -1.4(5) C10 C11 C12 C13 0.6(5) O1 C2 C3 C4 175.0(3) N1 C2 C3 C4 -7.1(3) C2 C3 C4 C5 15.9(3) C10 C9 C8 C13 -0.1(5) C10 C9 C8 S1 178.7(2) C11 C12 C13 C8 0.4(4) C11 C12 C13 C14 -178.5(3) C9 C8 C13 C12 -0.7(4) S1 C8 C13 C12 -179.7(2) C9 C8 C13 C14 178.4(3) S1 C8 C13 C14 -0.6(3) C5 C6 C7 C14 -20.3(4) C5 C6 C7 S1 161.2(2) C6 C7 C14 C13 -179.1(3) S1 C7 C14 C13 -0.5(3) C6 C7 C14 C15 1.1(5) S1 C7 C14 C15 179.8(2) C12 C13 C14 C7 179.6(3) C8 C13 C14 C7 0.7(4) C12 C13 C14 C15 -0.7(5) C8 C13 C14 C15 -179.6(3) N1 C15 C14 C7 -6.2(4) N1 C15 C14 C13 174.1(3) C7 C6 C5 N1 43.3(3) C7 C6 C5 C4 159.2(3) C3 C4 C5 N1 -18.4(3) C3 C4 C5 C6 -138.4(2) C22 C23 C24 C25 1.1(4) C23 C24 C25 C26 -0.6(5) C24 C25 C26 C27 -0.7(5) O2 C16 C17 C18 169.8(3) N2 C16 C17 C18 -8.9(4) C16 C17 C18 C19 17.6(4) C24 C23 C22 C27 -0.2(4) C24 C23 C22 S2 178.3(2) C25 C26 C27 C22 1.5(4) C25 C26 C27 C28 -175.3(3) C23 C22 C27 C26 -1.1(4) S2 C22 C27 C26 -179.8(2) C23 C22 C27 C28 176.3(3) S2 C22 C27 C28 -2.5(3) C19 C20 C21 C28 -21.4(4) C19 C20 C21 S2 160.9(2) C20 C21 C28 C27 -178.7(3) S2 C21 C28 C27 -0.9(3) C20 C21 C28 C29 1.1(4) S2 C21 C28 C29 179.0(2) C26 C27 C28 C21 179.2(3) C22 C27 C28 C21 2.2(3) C26 C27 C28 C29 -0.7(5) C22 C27 C28 C29 -177.7(2) N2 C29 C28 C21 -4.3(4) N2 C29 C28 C27 175.6(3) C21 C20 C19 N2 43.4(3) C21 C20 C19 C18 158.6(3) C17 C18 C19 N2 -19.3(3) C17 C18 C19 C20 -139.3(3) O1 C2 N1 C5 172.6(3) C3 C2 N1 C5 -5.3(3) O1 C2 N1 C15 6.3(5) C3 C2 N1 C15 -171.7(2) C6 C5 N1 C2 137.8(3) C4 C5 N1 C2 15.3(3) C6 C5 N1 C15 -55.6(3) C4 C5 N1 C15 -178.1(2) C14 C15 N1 C2 -159.5(3) C14 C15 N1 C5 35.0(4) O2 C16 N2 C29 8.5(5) C17 C16 N2 C29 -172.7(3) O2 C16 N2 C19 177.2(3) C17 C16 N2 C19 -4.1(4) C28 C29 N2 C16 -160.2(3) C28 C29 N2 C19 31.9(3) C20 C19 N2 C16 137.3(3) C18 C19 N2 C16 14.9(3) C20 C19 N2 C29 -53.8(3) C18 C19 N2 C29 -176.3(3) C9 C8 S1 C7 -178.7(3) C13 C8 S1 C7 0.3(2) C14 C7 S1 C8 0.1(2) C6 C7 S1 C8 178.8(3) C23 C22 S2 C21 -177.0(3) C27 C22 S2 C21 1.7(2) C28 C21 S2 C22 -0.5(2) C20 C21 S2 C22 177.5(3)