#------------------------------------------------------------------------------ #$Date: 2017-10-13 00:32:00 +0100 (Fri, 13 Oct 2017) $ #$Revision: 201954 $ #$URL: svn://www.crystallography.net/cod/cif/1/50/77/1507705.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_1507705 loop_ _publ_author_name 'Mitsudo, Koichi' 'Shimohara, Shuichi' 'Mizoguchi, Jun' 'Mandai, Hiroki' 'Suga, Seiji' _publ_section_title ; Synthesis of nitrogen-bridged terthiophenes by tandem buchwald-hartwig coupling and their properties. ; _journal_issue 11 _journal_name_full 'Organic letters' _journal_page_first 2702 _journal_page_last 2705 _journal_paper_doi 10.1021/ol300887t _journal_volume 14 _journal_year 2012 _chemical_formula_moiety 'C28 H38 N2 S3' _chemical_formula_sum 'C28 H38 N2 S3' _chemical_formula_weight 498.78 _chemical_name_systematic ; N,N'-Dioctyl-bis(dithienopyrrolo)thiophene ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_Int_Tables_number 2 _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 68.877(15) _cell_angle_beta 87.03(2) _cell_angle_gamma 77.71(2) _cell_formula_units_Z 2 _cell_length_a 9.282(5) _cell_length_b 11.353(5) _cell_length_c 13.670(7) _cell_measurement_reflns_used 3524 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 27.47 _cell_measurement_theta_min 3.10 _cell_volume 1312.4(11) _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_molecular_graphics 'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)' _computing_publication_material 'Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SIR2004 (Burla, et al., 2005)' _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 28.5714 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'Rigaku Saturn724' _diffrn_measurement_method dtprofit.ref _diffrn_radiation_monochromator Confocal _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71075 _diffrn_reflns_av_R_equivalents 0.0859 _diffrn_reflns_av_sigmaI/netI 0.0978 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 21265 _diffrn_reflns_theta_full 27.49 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_min 3.10 _exptl_absorpt_coefficient_mu 0.302 _exptl_absorpt_correction_T_max 0.988 _exptl_absorpt_correction_T_min 0.831 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_crystal_colour Orange _exptl_crystal_density_diffrn 1.262 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 536 _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.04 _refine_diff_density_max 0.368 _refine_diff_density_min -0.361 _refine_diff_density_rms 0.064 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 300 _refine_ls_number_reflns 5979 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.035 _refine_ls_R_factor_all 0.0758 _refine_ls_R_factor_gt 0.0502 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0433P)^2^+0.0772P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1031 _refine_ls_wR_factor_ref 0.1180 _reflns_number_gt 4247 _reflns_number_total 5979 _reflns_threshold_expression >2sigma(I) _iucr_refine_instructions_details ; TITL REM Yadorkari-X generated CELL 0.71075 9.2818 11.3532 13.6703 68.8770 87.0271 77.7085 ZERR 2.0 0.0045 0.0054 0.0070 0.0154 0.0240 0.0228 LATT 1 REM SPGR P-1 triclinic SFAC C H N S UNIT 56 76 4 6 SIZE 0.19 0.14 0.04 TEMP -172.8 L.S. 4 FMAP 2 PLAN -25 ACTA CONF BOND $H MERG 2 OMIT 5 1 1 OMIT -4 1 2 OMIT 3 0 7 OMIT -2 4 0 OMIT -1 -3 5 OMIT 1 -5 1 OMIT 1 -10 1 WGHT 0.043300 0.077200 FVAR 4.32617 S1 4 0.914750 0.077589 0.817655 11.00000 0.02550 0.01993 = 0.02649 -0.00608 0.00006 0.00292 S2 4 0.909114 0.442422 0.608288 11.00000 0.01177 0.02135 = 0.02221 -0.00672 0.00134 -0.00071 S3 4 0.821360 0.811062 0.392409 11.00000 0.01744 0.02162 = 0.02476 -0.00624 0.00390 -0.00546 N1 3 0.553423 0.324470 0.724144 11.00000 0.01460 0.01895 = 0.02853 -0.00974 0.00427 -0.00343 N2 3 0.512805 0.651614 0.543173 11.00000 0.01013 0.01934 = 0.02491 -0.00728 0.00148 -0.00190 C1 1 0.769411 0.005539 0.876500 11.00000 0.03511 0.01639 = 0.02718 -0.00292 0.00458 -0.00187 AFIX 43 H1 2 0.782750 -0.081321 0.923783 11.00000 -1.20000 AFIX 0 C2 1 0.633686 0.086071 0.848139 11.00000 0.02555 0.01999 = 0.02923 -0.00875 0.00373 -0.00331 AFIX 43 H2 2 0.542516 0.062771 0.873045 11.00000 -1.20000 AFIX 0 C3 1 0.648361 0.208420 0.776772 11.00000 0.02512 0.02329 = 0.02323 -0.01139 0.00540 -0.00619 C4 1 0.793645 0.220654 0.751598 11.00000 0.02113 0.01495 = 0.02099 -0.00900 -0.00034 0.00155 C5 1 0.787643 0.349788 0.682854 11.00000 0.01642 0.02317 = 0.02233 -0.01248 0.00269 -0.00651 C6 1 0.639685 0.412352 0.667172 11.00000 0.01607 0.02029 = 0.02045 -0.01186 0.00293 -0.00394 C7 1 0.622242 0.541940 0.591263 11.00000 0.01299 0.01557 = 0.02078 -0.01050 0.00021 0.00171 C8 1 0.759727 0.569487 0.553363 11.00000 0.01224 0.02463 = 0.02113 -0.01291 0.00162 -0.00166 C9 1 0.735018 0.696364 0.480426 11.00000 0.01532 0.02136 = 0.01964 -0.01058 0.00325 -0.00246 C10 1 0.582159 0.744870 0.475995 11.00000 0.01289 0.01962 = 0.02246 -0.00865 0.00069 0.00150 C11 1 0.535418 0.872647 0.403267 11.00000 0.01733 0.02568 = 0.02624 -0.00869 0.00309 -0.00232 AFIX 43 H11 2 0.435932 0.918918 0.391513 11.00000 -1.20000 AFIX 0 C12 1 0.653007 0.919720 0.352662 11.00000 0.02280 0.02440 = 0.02633 -0.00391 -0.00214 -0.00107 AFIX 43 H12 2 0.644115 1.003590 0.300769 11.00000 -1.20000 AFIX 0 C13 1 0.394256 0.351051 0.742984 11.00000 0.01510 0.02361 = 0.02927 -0.01123 0.00590 -0.00707 AFIX 23 H13 2 0.361635 0.268190 0.775468 11.00000 -1.20000 H13A 2 0.340143 0.398826 0.674961 11.00000 -1.20000 AFIX 0 C14 1 0.355829 0.428963 0.813597 11.00000 0.01698 0.02585 = 0.02285 -0.00804 0.00389 -0.00780 AFIX 23 H14 2 0.390926 0.510739 0.781870 11.00000 -1.20000 H14A 2 0.408396 0.380147 0.882087 11.00000 -1.20000 AFIX 0 C15 1 0.190201 0.460196 0.831944 11.00000 0.01724 0.02101 = 0.02634 -0.00681 0.00372 -0.00049 AFIX 23 H15 2 0.169321 0.532746 0.858050 11.00000 -1.20000 H15A 2 0.136411 0.489471 0.763881 11.00000 -1.20000 AFIX 0 C16 1 0.130827 0.348122 0.909085 11.00000 0.01809 0.02543 = 0.02203 -0.00593 0.00259 -0.00478 AFIX 23 H16 2 0.180216 0.322069 0.978370 11.00000 -1.20000 H16A 2 0.156404 0.273811 0.885192 11.00000 -1.20000 AFIX 0 C17 1 -0.035065 0.378505 0.921818 11.00000 0.01774 0.03365 = 0.02235 -0.00812 0.00306 -0.00682 AFIX 23 H17 2 -0.084702 0.401685 0.853057 11.00000 -1.20000 H17A 2 -0.061173 0.454507 0.943569 11.00000 -1.20000 AFIX 0 C18 1 -0.092847 0.266940 1.001886 11.00000 0.01899 0.03096 = 0.02284 -0.00928 0.00299 -0.00310 AFIX 23 H18 2 -0.054168 0.252110 1.072419 11.00000 -1.20000 H18A 2 -0.054310 0.187757 0.985924 11.00000 -1.20000 AFIX 0 C19 1 -0.261405 0.289240 1.004335 11.00000 0.02213 0.03797 = 0.02460 -0.01074 0.00601 -0.01073 AFIX 23 H19 2 -0.300605 0.364881 1.024955 11.00000 -1.20000 H19A 2 -0.301398 0.308352 0.933260 11.00000 -1.20000 AFIX 0 C20 1 -0.312212 0.170985 1.081605 11.00000 0.03163 0.05275 = 0.03705 -0.01801 0.01540 -0.02331 AFIX 137 H20 2 -0.276457 0.096739 1.059853 11.00000 -1.50000 H20A 2 -0.420224 0.188559 1.082522 11.00000 -1.50000 H20B 2 -0.272529 0.151840 1.151980 11.00000 -1.50000 AFIX 0 C21 1 0.352639 0.669245 0.547328 11.00000 0.00885 0.02567 = 0.02548 -0.01216 0.00168 -0.00248 AFIX 23 H21 2 0.326918 0.584298 0.585115 11.00000 -1.20000 H21A 2 0.311567 0.701189 0.474840 11.00000 -1.20000 AFIX 0 C22 1 0.279745 0.762983 0.600962 11.00000 0.01340 0.01978 = 0.02276 -0.00820 0.00178 -0.00102 AFIX 23 H22 2 0.312344 0.727811 0.675645 11.00000 -1.20000 H22A 2 0.310352 0.846574 0.567123 11.00000 -1.20000 AFIX 0 C23 1 0.112541 0.784001 0.593333 11.00000 0.01392 0.02262 = 0.02131 -0.00775 0.00197 -0.00127 AFIX 23 H23 2 0.081219 0.819005 0.518398 11.00000 -1.20000 H23A 2 0.083360 0.699627 0.626044 11.00000 -1.20000 AFIX 0 C24 1 0.032193 0.875348 0.645941 11.00000 0.01529 0.02342 = 0.02478 -0.00930 0.00437 -0.00242 AFIX 23 H24 2 0.051605 0.962532 0.607377 11.00000 -1.20000 H24A 2 0.073098 0.846370 0.718219 11.00000 -1.20000 AFIX 0 C25 1 -0.135430 0.884634 0.651013 11.00000 0.01327 0.01930 = 0.02429 -0.00870 0.00287 0.00319 AFIX 23 H25 2 -0.181609 0.958344 0.672399 11.00000 -1.20000 H25A 2 -0.174935 0.902035 0.580145 11.00000 -1.20000 AFIX 0 C26 1 -0.178190 0.761627 0.727906 11.00000 0.01549 0.02810 = 0.02349 -0.01022 0.00394 -0.00458 AFIX 23 H26 2 -0.138177 0.689466 0.703197 11.00000 -1.20000 H26A 2 -0.131398 0.740454 0.797294 11.00000 -1.20000 AFIX 0 C27 1 -0.344368 0.771769 0.741014 11.00000 0.01546 0.02768 = 0.02662 -0.01213 0.00215 -0.00097 AFIX 23 H27 2 -0.385238 0.844603 0.764755 11.00000 -1.20000 H27A 2 -0.391462 0.790715 0.672157 11.00000 -1.20000 AFIX 0 C28 1 -0.382251 0.648808 0.819468 11.00000 0.02107 0.03396 = 0.03372 -0.01405 0.00337 -0.01008 AFIX 137 H28 2 -0.337593 0.575559 0.798362 11.00000 -1.50000 H28A 2 -0.489605 0.657574 0.821286 11.00000 -1.50000 H28B 2 -0.343964 0.634066 0.889303 11.00000 -1.50000 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM REM R1 = 0.0502 for 4247 Fo > 4sig(Fo) and 0.0758 for all 5979 data REM 300 parameters refined using 0 restraints END WGHT 0.0433 0.0772 REM Highest difference peak 0.368, deepest hole -0.361, 1-sigma level 0.064 Q1 1 0.7033 0.0397 0.8716 11.00000 0.05 0.37 Q2 1 0.7077 0.7223 0.4979 11.00000 0.05 0.35 Q3 1 0.5564 0.7024 0.5094 11.00000 0.05 0.33 Q4 1 0.8391 0.0369 0.8517 11.00000 0.05 0.30 Q5 1 0.4983 0.3403 0.7254 11.00000 0.05 0.29 Q6 1 0.6330 0.7086 0.4737 11.00000 0.05 0.28 Q7 1 0.8323 0.4005 0.6258 11.00000 0.05 0.27 Q8 1 0.5376 0.8052 0.4402 11.00000 0.05 0.26 Q9 1 0.6147 0.4554 0.6309 11.00000 0.05 0.26 Q10 1 0.6984 0.5528 0.5740 11.00000 0.05 0.26 Q11 1 -0.1746 0.1618 1.1807 11.00000 0.05 0.25 Q12 1 0.5888 0.3665 0.6990 11.00000 0.05 0.25 Q13 1 0.8523 0.3805 0.6795 11.00000 0.05 0.25 Q14 1 0.7185 0.2092 0.7581 11.00000 0.05 0.25 Q15 1 -0.0736 0.3380 0.9684 11.00000 0.05 0.25 Q16 1 0.5575 0.5962 0.5609 11.00000 0.05 0.25 Q17 1 0.9315 0.0926 0.8957 11.00000 0.05 0.24 Q18 1 0.4197 0.6771 0.5356 11.00000 0.05 0.24 Q19 1 0.5872 0.5858 0.5854 11.00000 0.05 0.24 Q20 1 0.9915 0.0556 0.9647 11.00000 0.05 0.24 Q21 1 0.3124 0.6078 0.5644 11.00000 0.05 0.24 Q22 1 0.6910 1.0153 0.3423 11.00000 0.05 0.24 Q23 1 0.1251 0.6637 0.6716 11.00000 0.05 0.23 Q24 1 0.0724 0.8015 0.6396 11.00000 0.05 0.23 Q25 1 0.6605 0.3231 0.8257 11.00000 0.05 0.23 ; _cod_data_source_file ol300887t_si_001.cif _cod_data_source_block 2e _cod_original_cell_volume 1312.5(11) _cod_database_code 1507705 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags S1 S 0.91475(6) 0.07759(6) 0.81765(5) 0.02580(16) Uani 1 1 d . S2 S 0.90911(5) 0.44242(5) 0.60829(5) 0.01922(15) Uani 1 1 d . S3 S 0.82136(6) 0.81106(6) 0.39241(5) 0.02176(15) Uani 1 1 d . N1 N 0.55342(18) 0.32447(18) 0.72414(15) 0.0205(4) Uani 1 1 d . N2 N 0.51280(17) 0.65161(17) 0.54317(15) 0.0185(4) Uani 1 1 d . C1 C 0.7694(3) 0.0055(2) 0.87650(19) 0.0283(6) Uani 1 1 d . H1 H 0.7828 -0.0813 0.9238 0.034 Uiso 1 1 calc R C2 C 0.6337(2) 0.0861(2) 0.84814(19) 0.0253(5) Uani 1 1 d . H2 H 0.5425 0.0628 0.8730 0.030 Uiso 1 1 calc R C3 C 0.6484(2) 0.2084(2) 0.77677(19) 0.0230(5) Uani 1 1 d . C4 C 0.7936(2) 0.2207(2) 0.75160(18) 0.0191(5) Uani 1 1 d . C5 C 0.7876(2) 0.3498(2) 0.68285(18) 0.0191(5) Uani 1 1 d . C6 C 0.6397(2) 0.4124(2) 0.66717(17) 0.0177(5) Uani 1 1 d . C7 C 0.6222(2) 0.5419(2) 0.59126(17) 0.0161(5) Uani 1 1 d . C8 C 0.7597(2) 0.5695(2) 0.55336(18) 0.0184(5) Uani 1 1 d . C9 C 0.7350(2) 0.6964(2) 0.48043(17) 0.0182(5) Uani 1 1 d . C10 C 0.5822(2) 0.7449(2) 0.47599(18) 0.0188(5) Uani 1 1 d . C11 C 0.5354(2) 0.8726(2) 0.40327(18) 0.0237(5) Uani 1 1 d . H11 H 0.4359 0.9189 0.3915 0.028 Uiso 1 1 calc R C12 C 0.6530(2) 0.9197(2) 0.35266(19) 0.0265(6) Uani 1 1 d . H12 H 0.6441 1.0036 0.3008 0.032 Uiso 1 1 calc R C13 C 0.3943(2) 0.3511(2) 0.74298(19) 0.0219(5) Uani 1 1 d . H13 H 0.3616 0.2682 0.7755 0.026 Uiso 1 1 calc R H13A H 0.3401 0.3988 0.6750 0.026 Uiso 1 1 calc R C14 C 0.3558(2) 0.4290(2) 0.81360(18) 0.0217(5) Uani 1 1 d . H14 H 0.3909 0.5107 0.7819 0.026 Uiso 1 1 calc R H14A H 0.4084 0.3801 0.8821 0.026 Uiso 1 1 calc R C15 C 0.1902(2) 0.4602(2) 0.83194(19) 0.0227(5) Uani 1 1 d . H15 H 0.1693 0.5327 0.8581 0.027 Uiso 1 1 calc R H15A H 0.1364 0.4895 0.7639 0.027 Uiso 1 1 calc R C16 C 0.1308(2) 0.3481(2) 0.90909(18) 0.0226(5) Uani 1 1 d . H16 H 0.1802 0.3221 0.9784 0.027 Uiso 1 1 calc R H16A H 0.1564 0.2738 0.8852 0.027 Uiso 1 1 calc R C17 C -0.0351(2) 0.3785(2) 0.92182(19) 0.0250(5) Uani 1 1 d . H17 H -0.0847 0.4017 0.8531 0.030 Uiso 1 1 calc R H17A H -0.0612 0.4545 0.9436 0.030 Uiso 1 1 calc R C18 C -0.0928(2) 0.2669(2) 1.00189(19) 0.0248(5) Uani 1 1 d . H18 H -0.0542 0.2521 1.0724 0.030 Uiso 1 1 calc R H18A H -0.0543 0.1878 0.9859 0.030 Uiso 1 1 calc R C19 C -0.2614(2) 0.2892(2) 1.0043(2) 0.0279(6) Uani 1 1 d . H19 H -0.3006 0.3649 1.0250 0.033 Uiso 1 1 calc R H19A H -0.3014 0.3084 0.9333 0.033 Uiso 1 1 calc R C20 C -0.3122(3) 0.1710(3) 1.0816(2) 0.0382(7) Uani 1 1 d . H20 H -0.2765 0.0967 1.0599 0.057 Uiso 1 1 calc R H20A H -0.4202 0.1886 1.0825 0.057 Uiso 1 1 calc R H20B H -0.2725 0.1518 1.1520 0.057 Uiso 1 1 calc R C21 C 0.3526(2) 0.6692(2) 0.54733(18) 0.0194(5) Uani 1 1 d . H21 H 0.3269 0.5843 0.5851 0.023 Uiso 1 1 calc R H21A H 0.3116 0.7012 0.4748 0.023 Uiso 1 1 calc R C22 C 0.2797(2) 0.7630(2) 0.60096(18) 0.0189(5) Uani 1 1 d . H22 H 0.3123 0.7278 0.6756 0.023 Uiso 1 1 calc R H22A H 0.3104 0.8466 0.5671 0.023 Uiso 1 1 calc R C23 C 0.1125(2) 0.7840(2) 0.59333(18) 0.0198(5) Uani 1 1 d . H23 H 0.0812 0.8190 0.5184 0.024 Uiso 1 1 calc R H23A H 0.0834 0.6996 0.6260 0.024 Uiso 1 1 calc R C24 C 0.0322(2) 0.8753(2) 0.64594(18) 0.0214(5) Uani 1 1 d . H24 H 0.0516 0.9625 0.6074 0.026 Uiso 1 1 calc R H24A H 0.0731 0.8464 0.7182 0.026 Uiso 1 1 calc R C25 C -0.1354(2) 0.8846(2) 0.65101(18) 0.0198(5) Uani 1 1 d . H25 H -0.1816 0.9583 0.6724 0.024 Uiso 1 1 calc R H25A H -0.1749 0.9020 0.5801 0.024 Uiso 1 1 calc R C26 C -0.1782(2) 0.7616(2) 0.72791(18) 0.0222(5) Uani 1 1 d . H26 H -0.1382 0.6895 0.7032 0.027 Uiso 1 1 calc R H26A H -0.1314 0.7405 0.7973 0.027 Uiso 1 1 calc R C27 C -0.3444(2) 0.7718(2) 0.74101(19) 0.0232(5) Uani 1 1 d . H27 H -0.3852 0.8446 0.7648 0.028 Uiso 1 1 calc R H27A H -0.3915 0.7907 0.6722 0.028 Uiso 1 1 calc R C28 C -0.3823(2) 0.6488(2) 0.8195(2) 0.0284(6) Uani 1 1 d . H28 H -0.3376 0.5756 0.7984 0.043 Uiso 1 1 calc R H28A H -0.4896 0.6576 0.8213 0.043 Uiso 1 1 calc R H28B H -0.3440 0.6341 0.8893 0.043 Uiso 1 1 calc R 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 0.0255(3) 0.0199(3) 0.0265(3) -0.0061(3) 0.0001(3) 0.0029(2) S2 0.0118(2) 0.0214(3) 0.0222(3) -0.0067(2) 0.0013(2) -0.0007(2) S3 0.0174(3) 0.0216(3) 0.0248(3) -0.0062(3) 0.0039(2) -0.0055(2) N1 0.0146(8) 0.0190(10) 0.0285(11) -0.0097(9) 0.0043(8) -0.0034(7) N2 0.0101(8) 0.0193(10) 0.0249(10) -0.0073(8) 0.0015(7) -0.0019(7) C1 0.0351(13) 0.0164(13) 0.0272(13) -0.0029(11) 0.0046(11) -0.0019(10) C2 0.0256(11) 0.0200(13) 0.0292(13) -0.0088(11) 0.0037(10) -0.0033(10) C3 0.0251(11) 0.0233(13) 0.0232(12) -0.0114(11) 0.0054(10) -0.0062(10) C4 0.0211(10) 0.0149(12) 0.0210(12) -0.0090(10) -0.0003(9) 0.0016(8) C5 0.0164(10) 0.0232(13) 0.0223(12) -0.0125(10) 0.0027(9) -0.0065(9) C6 0.0161(9) 0.0203(12) 0.0205(12) -0.0119(10) 0.0029(9) -0.0039(9) C7 0.0130(9) 0.0156(11) 0.0208(11) -0.0105(10) 0.0002(9) 0.0017(8) C8 0.0122(9) 0.0246(13) 0.0211(12) -0.0129(10) 0.0016(9) -0.0017(9) C9 0.0153(9) 0.0214(12) 0.0196(12) -0.0106(10) 0.0033(9) -0.0025(9) C10 0.0129(9) 0.0196(12) 0.0225(12) -0.0086(10) 0.0007(9) 0.0015(8) C11 0.0173(10) 0.0257(13) 0.0262(13) -0.0087(11) 0.0031(10) -0.0023(9) C12 0.0228(11) 0.0244(13) 0.0263(13) -0.0039(11) -0.0021(10) -0.0011(10) C13 0.0151(9) 0.0236(13) 0.0293(13) -0.0112(11) 0.0059(10) -0.0071(9) C14 0.0170(10) 0.0258(13) 0.0228(12) -0.0080(11) 0.0039(9) -0.0078(9) C15 0.0172(10) 0.0210(13) 0.0263(13) -0.0068(10) 0.0037(10) -0.0005(9) C16 0.0181(10) 0.0254(13) 0.0220(12) -0.0059(10) 0.0026(9) -0.0048(9) C17 0.0177(10) 0.0337(15) 0.0224(12) -0.0081(11) 0.0031(9) -0.0068(10) C18 0.0190(10) 0.0310(14) 0.0228(12) -0.0093(11) 0.0030(10) -0.0031(10) C19 0.0221(11) 0.0380(15) 0.0246(13) -0.0107(12) 0.0060(10) -0.0107(10) C20 0.0316(13) 0.0528(19) 0.0371(16) -0.0180(14) 0.0154(12) -0.0233(13) C21 0.0089(9) 0.0257(13) 0.0255(12) -0.0122(11) 0.0017(9) -0.0025(8) C22 0.0134(9) 0.0198(12) 0.0228(12) -0.0082(10) 0.0018(9) -0.0010(8) C23 0.0139(9) 0.0226(13) 0.0213(12) -0.0078(10) 0.0020(9) -0.0013(8) C24 0.0153(10) 0.0234(13) 0.0248(13) -0.0093(11) 0.0044(9) -0.0024(9) C25 0.0133(9) 0.0193(12) 0.0243(12) -0.0087(10) 0.0029(9) 0.0032(8) C26 0.0155(10) 0.0281(14) 0.0235(13) -0.0102(11) 0.0039(9) -0.0046(9) C27 0.0155(10) 0.0277(14) 0.0266(13) -0.0121(11) 0.0021(10) -0.0010(9) C28 0.0211(11) 0.0340(15) 0.0337(14) -0.0141(12) 0.0034(11) -0.0101(10) 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 C4 S1 C1 91.07(11) C5 S2 C8 89.43(11) C9 S3 C12 91.33(11) C3 N1 C6 107.54(17) C3 N1 C13 123.68(18) C6 N1 C13 127.94(19) C10 N2 C7 107.27(16) C10 N2 C21 122.33(18) C7 N2 C21 129.99(18) C2 C1 S1 113.52(18) C2 C1 H1 123.2 S1 C1 H1 123.2 C1 C2 C3 110.5(2) C1 C2 H2 124.8 C3 C2 H2 124.8 N1 C3 C4 109.3(2) N1 C3 C2 136.0(2) C4 C3 C2 114.7(2) C3 C4 C5 106.93(19) C3 C4 S1 110.25(17) C5 C4 S1 142.76(17) C6 C5 C4 107.54(19) C6 C5 S2 114.40(18) C4 C5 S2 137.81(16) C5 C6 N1 108.7(2) C5 C6 C7 111.33(19) N1 C6 C7 139.69(19) N2 C7 C8 108.32(19) N2 C7 C6 140.78(18) C8 C7 C6 110.89(18) C9 C8 C7 107.98(18) C9 C8 S2 138.08(16) C7 C8 S2 113.95(17) C8 C9 C10 106.56(19) C8 C9 S3 143.50(16) C10 C9 S3 109.89(17) N2 C10 C9 109.86(19) N2 C10 C11 135.48(18) C9 C10 C11 114.6(2) C12 C11 C10 110.66(19) C12 C11 H11 124.7 C10 C11 H11 124.7 C11 C12 S3 113.50(18) C11 C12 H12 123.3 S3 C12 H12 123.3 N1 C13 C14 112.44(17) N1 C13 H13 109.1 C14 C13 H13 109.1 N1 C13 H13A 109.1 C14 C13 H13A 109.1 H13 C13 H13A 107.8 C13 C14 C15 113.13(18) C13 C14 H14 109.0 C15 C14 H14 109.0 C13 C14 H14A 109.0 C15 C14 H14A 109.0 H14 C14 H14A 107.8 C16 C15 C14 114.49(19) C16 C15 H15 108.6 C14 C15 H15 108.6 C16 C15 H15A 108.6 C14 C15 H15A 108.6 H15 C15 H15A 107.6 C15 C16 C17 113.82(19) C15 C16 H16 108.8 C17 C16 H16 108.8 C15 C16 H16A 108.8 C17 C16 H16A 108.8 H16 C16 H16A 107.7 C16 C17 C18 113.4(2) C16 C17 H17 108.9 C18 C17 H17 108.9 C16 C17 H17A 108.9 C18 C17 H17A 108.9 H17 C17 H17A 107.7 C17 C18 C19 113.8(2) C17 C18 H18 108.8 C19 C18 H18 108.8 C17 C18 H18A 108.8 C19 C18 H18A 108.8 H18 C18 H18A 107.7 C20 C19 C18 111.3(2) C20 C19 H19 109.4 C18 C19 H19 109.4 C20 C19 H19A 109.4 C18 C19 H19A 109.4 H19 C19 H19A 108.0 C19 C20 H20 109.5 C19 C20 H20A 109.5 H20 C20 H20A 109.5 C19 C20 H20B 109.5 H20 C20 H20B 109.5 H20A C20 H20B 109.5 N2 C21 C22 114.15(17) N2 C21 H21 108.7 C22 C21 H21 108.7 N2 C21 H21A 108.7 C22 C21 H21A 108.7 H21 C21 H21A 107.6 C23 C22 C21 110.37(17) C23 C22 H22 109.6 C21 C22 H22 109.6 C23 C22 H22A 109.6 C21 C22 H22A 109.6 H22 C22 H22A 108.1 C24 C23 C22 113.43(18) C24 C23 H23 108.9 C22 C23 H23 108.9 C24 C23 H23A 108.9 C22 C23 H23A 108.9 H23 C23 H23A 107.7 C23 C24 C25 114.10(18) C23 C24 H24 108.7 C25 C24 H24 108.7 C23 C24 H24A 108.7 C25 C24 H24A 108.7 H24 C24 H24A 107.6 C26 C25 C24 112.89(18) C26 C25 H25 109.0 C24 C25 H25 109.0 C26 C25 H25A 109.0 C24 C25 H25A 109.0 H25 C25 H25A 107.8 C27 C26 C25 114.05(19) C27 C26 H26 108.7 C25 C26 H26 108.7 C27 C26 H26A 108.7 C25 C26 H26A 108.7 H26 C26 H26A 107.6 C28 C27 C26 112.48(19) C28 C27 H27 109.1 C26 C27 H27 109.1 C28 C27 H27A 109.1 C26 C27 H27A 109.1 H27 C27 H27A 107.8 C27 C28 H28 109.5 C27 C28 H28A 109.5 H28 C28 H28A 109.5 C27 C28 H28B 109.5 H28 C28 H28B 109.5 H28A C28 H28B 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 C4 1.729(2) S1 C1 1.738(2) S2 C5 1.740(2) S2 C8 1.744(2) S3 C9 1.732(2) S3 C12 1.744(2) N1 C3 1.385(3) N1 C6 1.399(3) N1 C13 1.472(2) N2 C10 1.381(3) N2 C7 1.398(3) N2 C21 1.458(2) C1 C2 1.370(3) C1 H1 0.9500 C2 C3 1.411(3) C2 H2 0.9500 C3 C4 1.398(3) C4 C5 1.419(3) C5 C6 1.394(3) C6 C7 1.443(3) C7 C8 1.407(3) C8 C9 1.403(3) C9 C10 1.404(3) C10 C11 1.421(3) C11 C12 1.363(3) C11 H11 0.9500 C12 H12 0.9500 C13 C14 1.512(3) C13 H13 0.9900 C13 H13A 0.9900 C14 C15 1.531(3) C14 H14 0.9900 C14 H14A 0.9900 C15 C16 1.519(3) C15 H15 0.9900 C15 H15A 0.9900 C16 C17 1.520(3) C16 H16 0.9900 C16 H16A 0.9900 C17 C18 1.523(3) C17 H17 0.9900 C17 H17A 0.9900 C18 C19 1.531(3) C18 H18 0.9900 C18 H18A 0.9900 C19 C20 1.529(3) C19 H19 0.9900 C19 H19A 0.9900 C20 H20 0.9800 C20 H20A 0.9800 C20 H20B 0.9800 C21 C22 1.527(3) C21 H21 0.9900 C21 H21A 0.9900 C22 C23 1.522(3) C22 H22 0.9900 C22 H22A 0.9900 C23 C24 1.517(3) C23 H23 0.9900 C23 H23A 0.9900 C24 C25 1.536(3) C24 H24 0.9900 C24 H24A 0.9900 C25 C26 1.532(3) C25 H25 0.9900 C25 H25A 0.9900 C26 C27 1.528(3) C26 H26 0.9900 C26 H26A 0.9900 C27 C28 1.521(3) C27 H27 0.9900 C27 H27A 0.9900 C28 H28 0.9800 C28 H28A 0.9800 C28 H28B 0.9800 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 C4 S1 C1 C2 -0.3(2) S1 C1 C2 C3 0.3(3) C6 N1 C3 C4 -1.6(3) C13 N1 C3 C4 -171.8(2) C6 N1 C3 C2 177.4(3) C13 N1 C3 C2 7.2(4) C1 C2 C3 N1 -179.1(3) C1 C2 C3 C4 -0.2(3) N1 C3 C4 C5 1.3(3) C2 C3 C4 C5 -177.9(2) N1 C3 C4 S1 179.23(16) C2 C3 C4 S1 0.0(3) C1 S1 C4 C3 0.13(18) C1 S1 C4 C5 176.8(3) C3 C4 C5 C6 -0.5(3) S1 C4 C5 C6 -177.3(2) C3 C4 C5 S2 -174.1(2) S1 C4 C5 S2 9.1(5) C8 S2 C5 C6 -0.12(19) C8 S2 C5 C4 173.2(3) C4 C5 C6 N1 -0.4(3) S2 C5 C6 N1 174.85(14) C4 C5 C6 C7 -175.38(18) S2 C5 C6 C7 -0.1(3) C3 N1 C6 C5 1.3(2) C13 N1 C6 C5 170.9(2) C3 N1 C6 C7 173.9(3) C13 N1 C6 C7 -16.4(4) C10 N2 C7 C8 0.5(2) C21 N2 C7 C8 173.2(2) C10 N2 C7 C6 179.2(3) C21 N2 C7 C6 -8.1(4) C5 C6 C7 N2 -178.4(3) N1 C6 C7 N2 9.0(5) C5 C6 C7 C8 0.3(3) N1 C6 C7 C8 -172.3(3) N2 C7 C8 C9 -0.7(2) C6 C7 C8 C9 -179.89(18) N2 C7 C8 S2 178.75(15) C6 C7 C8 S2 -0.4(2) C5 S2 C8 C9 179.6(3) C5 S2 C8 C7 0.30(18) C7 C8 C9 C10 0.7(3) S2 C8 C9 C10 -178.6(2) C7 C8 C9 S3 -176.3(2) S2 C8 C9 S3 4.4(5) C12 S3 C9 C8 177.0(3) C12 S3 C9 C10 0.13(18) C7 N2 C10 C9 0.0(3) C21 N2 C10 C9 -173.43(19) C7 N2 C10 C11 177.4(3) C21 N2 C10 C11 4.0(4) C8 C9 C10 N2 -0.4(3) S3 C9 C10 N2 177.67(15) C8 C9 C10 C11 -178.4(2) S3 C9 C10 C11 -0.3(3) N2 C10 C11 C12 -176.9(2) C9 C10 C11 C12 0.4(3) C10 C11 C12 S3 -0.3(3) C9 S3 C12 C11 0.1(2) C3 N1 C13 C14 99.8(3) C6 N1 C13 C14 -68.3(3) N1 C13 C14 C15 178.65(19) C13 C14 C15 C16 76.6(3) C14 C15 C16 C17 -176.78(19) C15 C16 C17 C18 -178.2(2) C16 C17 C18 C19 -171.9(2) C17 C18 C19 C20 176.8(2) C10 N2 C21 C22 -73.7(3) C7 N2 C21 C22 114.6(2) N2 C21 C22 C23 175.17(18) C21 C22 C23 C24 179.45(19) C22 C23 C24 C25 -172.80(19) C23 C24 C25 C26 70.4(3) C24 C25 C26 C27 175.48(18) C25 C26 C27 C28 -178.9(2) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 30651900