#------------------------------------------------------------------------------ #$Date: 2021-10-29 05:26:17 +0300 (Fri, 29 Oct 2021) $ #$Revision: 270146 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/37/7243787.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_7243787 loop_ _publ_author_name 'Zhou, Lu' 'Chen, Zhaopeng' 'Li, Jiahui' 'Li, Baolin' _publ_section_title ; Synthesis of dithienofurans via cascade copper catalysed dual C--S coupling and ring closure reactions under mild conditions ; _journal_issue 54 _journal_name_full 'RSC Advances' _journal_page_first 34071 _journal_page_last 34078 _journal_paper_doi 10.1039/D1RA06881D _journal_volume 11 _journal_year 2021 _chemical_formula_moiety 'C20 H12 O S2' _chemical_formula_sum 'C20 H12 O S2' _chemical_formula_weight 332.42 _chemical_name_common 2,6-diphenyldithieno[3,2-b:2',3'-d]furan _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 geom _atom_sites_solution_primary direct _audit_creation_date 2021-04-09 _audit_creation_method ; Olex2 1.3 (compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145) ; _audit_update_record ; 2021-10-12 deposited with the CCDC. 2021-10-12 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 97.279(14) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 16.763(2) _cell_length_b 5.6910(10) _cell_length_c 7.7824(11) _cell_measurement_reflns_used 1047 _cell_measurement_temperature 150.00(10) _cell_measurement_theta_max 27.7300 _cell_measurement_theta_min 2.4400 _cell_volume 736.44(19) _computing_cell_refinement 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 150.00(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 10.5368 _diffrn_detector_type AtlasS2 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.883 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -80.00 16.00 0.75 2.00 -- -11.27 -57.00-180.00 128 2 \w -26.00 53.50 0.75 2.00 -- -11.27 0.00-180.00 106 3 \w 69.00 96.00 0.75 2.00 -- 11.90-178.00 30.00 36 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, AtlasS2' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0303270000 _diffrn_orient_matrix_UB_12 0.0420222000 _diffrn_orient_matrix_UB_13 -0.0645495000 _diffrn_orient_matrix_UB_21 -0.0283255000 _diffrn_orient_matrix_UB_22 -0.0034557000 _diffrn_orient_matrix_UB_23 0.0602932000 _diffrn_orient_matrix_UB_31 0.0100299000 _diffrn_orient_matrix_UB_32 0.1173739000 _diffrn_orient_matrix_UB_33 0.0248258000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0241 _diffrn_reflns_av_unetI/netI 0.0462 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.883 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 3848 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.883 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 29.298 _diffrn_reflns_theta_min 2.450 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Mo) X-ray Source' _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.362 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.81337 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.499 _exptl_crystal_description block _exptl_crystal_F_000 344 _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.303 _refine_diff_density_min -0.333 _refine_diff_density_rms 0.055 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 184 _refine_ls_number_reflns 1776 _refine_ls_number_restraints 186 _refine_ls_restrained_S_all 1.022 _refine_ls_R_factor_all 0.0940 _refine_ls_R_factor_gt 0.0610 _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^)+(0.0441P)^2^+0.5665P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1248 _refine_ls_wR_factor_ref 0.1449 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1253 _reflns_number_total 1776 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ra06881d2.cif _cod_data_source_block 2959 _cod_original_cell_volume 736.4(2) _cod_database_code 7243787 _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_max 0.958 _shelx_estimated_absorpt_t_min 0.951 _reflns_odcompleteness_completeness 99.52 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups 2. Rigid body (RIGU) restrains C6, S2, C8, C5, C7, C15, C4, C16, C20, S1, C3, O1, C17, C19, C1, C2, C18, C9, C10, C14, C11, C13, C12 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002 3. Others Fixed Sof: S1(0.5) S2(0.5) O1(0.5) C1(0.5) C2(0.5) H2(0.5) C3(0.5) C4(0.5) C5(0.5) C6(0.5) C7(0.5) H7(0.5) C8(0.5) C9(0.5) C10(0.5) H10(0.5) C11(0.5) H11(0.5) C12(0.5) H12(0.5) C13(0.5) H13(0.5) C14(0.5) H14(0.5) C15(0.5) C16(0.5) H16(0.5) C17(0.5) H17(0.5) C18(0.5) H18(0.5) C19(0.5) H19(0.5) C20(0.5) H20(0.5) 4.a Aromatic/amide H refined with riding coordinates: C2(H2), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20) 4.b Fitted hexagon refined as free rotating group: C9(C10,C11,C12,C13,C14), C15(C16,C17,C18,C19,C20) ; _shelx_res_file ; TITL 2959_a.res in P2(1)/c 2959.res created by SHELXL-2018/3 at 20:39:03 on 08-Apr-2021 REM Old TITL 2959 in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.367, Rweak 0.025, Alpha 0.047 REM 0.573 for 163 systematic absences, Orientation as input REM Formula found by SHELXT: C11 S CELL 0.71073 16.7628 5.691 7.7824 90 97.279 90 ZERR 2 0.0024 0.001 0.0011 0 0.014 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H O S UNIT 40 24 2 4 RIGU 0.001 0.002 C6 S2 C8 C5 C7 C15 C4 C16 C20 S1 C3 O1 C17 C19 C1 C2 C18 = C9 C10 C14 C11 C13 C12 L.S. 10 PLAN 2 SIZE 0.12 0.13 0.14 TEMP -123.15(10) CONF BOND list 4 MORE -1 BOND $H fmap 2 acta REM REM REM WGHT 0.044100 0.566500 FVAR 0.63217 PART -1 S1 4 0.603349 0.645577 0.365019 10.50000 0.02964 0.03674 = 0.02863 0.00899 0.00498 0.00232 S2 4 0.364636 0.649233 0.485790 10.50000 0.02861 0.03324 = 0.02637 0.00485 0.00386 0.00588 O1 3 0.512574 0.146318 0.603161 10.50000 0.03549 0.03381 = 0.02960 0.01034 0.00624 0.00716 C1 1 0.676336 0.428279 0.419613 10.50000 0.02631 0.03412 = 0.01606 0.00141 0.00111 0.00451 C2 1 0.645656 0.235153 0.505650 10.50000 0.03733 0.02592 = 0.02525 0.00436 0.00343 0.00794 AFIX 43 H2 2 0.674981 0.098228 0.544470 10.50000 -1.20000 AFIX 0 C3 1 0.566224 0.278687 0.523750 10.50000 0.03305 0.03263 = 0.01746 0.00567 0.00062 0.00526 C4 1 0.533356 0.485759 0.457217 10.50000 0.02476 0.02837 = 0.01128 0.00057 -0.00259 0.00243 C5 1 0.452296 0.488638 0.497922 10.50000 0.02618 0.03239 = 0.00971 -0.00210 -0.00144 0.00150 C6 1 0.444527 0.281167 0.586133 10.50000 0.03502 0.03220 = 0.01649 -0.00009 0.00272 0.00635 C7 1 0.369196 0.240055 0.643495 10.50000 0.03442 0.02908 = 0.02656 -0.00022 -0.00121 -0.00742 AFIX 43 H7 2 0.354905 0.103909 0.703287 10.50000 -1.20000 AFIX 0 C8 1 0.319254 0.431450 0.598200 10.50000 0.02635 0.03304 = 0.01821 -0.00218 0.00145 -0.00661 AFIX 66 C9 1 0.758528 0.455767 0.369595 10.50000 0.01957 0.06232 = 0.01606 -0.01126 -0.00483 -0.00431 C10 1 0.817459 0.289845 0.422081 10.50000 0.03259 0.07831 = 0.01549 -0.00971 0.00330 0.01423 AFIX 43 H10 2 0.804389 0.154203 0.483956 10.50000 -1.20000 AFIX 65 C11 1 0.895514 0.322387 0.384036 10.50000 0.03058 0.11605 = 0.01465 -0.00273 0.00300 0.01591 AFIX 43 H11 2 0.935791 0.208986 0.419908 10.50000 -1.20000 AFIX 65 C12 1 0.914638 0.520852 0.293504 10.50000 0.02731 0.12867 = 0.02326 0.00486 0.00000 0.00714 AFIX 43 H12 2 0.967985 0.543092 0.267503 10.50000 -1.20000 AFIX 65 C13 1 0.855708 0.686776 0.241017 10.50000 0.01836 0.11783 = 0.02262 0.01075 -0.00536 -0.00592 AFIX 43 H13 2 0.868779 0.822417 0.179142 10.50000 -1.20000 AFIX 65 C14 1 0.777653 0.654237 0.279061 10.50000 0.01838 0.08031 = 0.02551 0.00280 -0.00437 -0.00569 AFIX 43 H14 2 0.737376 0.767638 0.243188 10.50000 -1.20000 AFIX 66 C15 1 0.233539 0.458964 0.627795 10.50000 0.02447 0.06023 = 0.01704 -0.01581 0.00047 -0.00546 C16 1 0.188776 0.651647 0.561726 10.50000 0.03217 0.07403 = 0.02204 -0.00935 0.01087 0.00801 AFIX 43 H16 2 0.212510 0.766597 0.495652 10.50000 -1.20000 AFIX 65 C17 1 0.109286 0.676141 0.592332 10.50000 0.03101 0.11749 = 0.02254 0.00378 0.00855 0.01657 AFIX 43 H17 2 0.078692 0.807832 0.547176 10.50000 -1.20000 AFIX 65 C18 1 0.074558 0.507952 0.689007 10.50000 0.02194 0.12592 = 0.01683 -0.00208 -0.00274 0.00096 AFIX 43 H18 2 0.020230 0.524694 0.709925 10.50000 -1.20000 AFIX 65 C19 1 0.119320 0.315268 0.755077 10.50000 0.01790 0.11468 = 0.02354 0.00075 -0.00319 -0.01049 AFIX 43 H19 2 0.095584 0.200319 0.821151 10.50000 -1.20000 AFIX 65 C20 1 0.198810 0.290771 0.724473 10.50000 0.01746 0.08354 = 0.02285 0.00057 -0.00657 -0.01202 AFIX 43 H20 2 0.229403 0.159080 0.769629 10.50000 -1.20000 AFIX 0 HKLF 4 REM 2959_a.res in P2(1)/c REM wR2 = 0.1449, GooF = S = 1.046, Restrained GooF = 1.022 for all data REM R1 = 0.0610 for 1253 Fo > 4sig(Fo) and 0.0940 for all 1776 data REM 184 parameters refined using 186 restraints END WGHT 0.0444 0.5592 REM Highest difference peak 0.303, deepest hole -0.333, 1-sigma level 0.055 Q1 1 0.4129 0.2182 0.6173 11.00000 0.05 0.30 Q2 1 0.4579 0.3968 0.6194 11.00000 0.05 0.28 ; _shelx_res_checksum 17797 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.233 _oxdiff_exptl_absorpt_empirical_full_min 0.736 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 0.60335(8) 0.6456(2) 0.36502(15) 0.0316(3) Uani 0.5 1 d . . P A -1 S2 S 0.36464(7) 0.6492(3) 0.48579(17) 0.0294(3) Uani 0.5 1 d . . P A -1 O1 O 0.51257(18) 0.1463(5) 0.6032(4) 0.0328(7) Uani 0.5 1 d . . P A -1 C1 C 0.6763(3) 0.4283(9) 0.4196(5) 0.0256(9) Uani 0.5 1 d . . P A -1 C2 C 0.6457(3) 0.2352(10) 0.5056(7) 0.0295(11) Uani 0.5 1 d . . P A -1 H2 H 0.674981 0.098228 0.544470 0.035 Uiso 0.5 1 calc R U P A -1 C3 C 0.5662(3) 0.2787(8) 0.5237(5) 0.0279(8) Uani 0.5 1 d . . P A -1 C4 C 0.5334(6) 0.4858(17) 0.4572(10) 0.0219(15) Uani 0.5 1 d . . P A -1 C5 C 0.4523(6) 0.4886(18) 0.4979(10) 0.0231(14) Uani 0.5 1 d . . P A -1 C6 C 0.4445(3) 0.2812(8) 0.5861(5) 0.0279(8) Uani 0.5 1 d . . P A -1 C7 C 0.3692(3) 0.2401(10) 0.6435(6) 0.0305(9) Uani 0.5 1 d . . P A -1 H7 H 0.354905 0.103909 0.703287 0.037 Uiso 0.5 1 calc R U P A -1 C8 C 0.3193(3) 0.4315(9) 0.5982(5) 0.0260(8) Uani 0.5 1 d . . P A -1 C9 C 0.7585(3) 0.4558(10) 0.3696(10) 0.0333(15) Uani 0.5 1 d G . P A -1 C10 C 0.8175(5) 0.2898(12) 0.4221(14) 0.042(2) Uani 0.5 1 d G . P A -1 H10 H 0.804389 0.154203 0.483956 0.051 Uiso 0.5 1 calc R U P A -1 C11 C 0.8955(4) 0.3224(18) 0.3840(18) 0.054(2) Uani 0.5 1 d G . P A -1 H11 H 0.935791 0.208986 0.419908 0.064 Uiso 0.5 1 calc R U P A -1 C12 C 0.9146(3) 0.521(2) 0.2935(18) 0.060(3) Uani 0.5 1 d G . P A -1 H12 H 0.967985 0.543092 0.267503 0.072 Uiso 0.5 1 calc R U P A -1 C13 C 0.8557(3) 0.6868(15) 0.2410(13) 0.054(2) Uani 0.5 1 d G . P A -1 H13 H 0.868779 0.822417 0.179142 0.064 Uiso 0.5 1 calc R U P A -1 C14 C 0.7777(3) 0.6542(11) 0.2791(10) 0.0420(16) Uani 0.5 1 d G . P A -1 H14 H 0.737376 0.767638 0.243188 0.050 Uiso 0.5 1 calc R U P A -1 C15 C 0.2335(3) 0.4590(10) 0.6278(11) 0.0341(15) Uani 0.5 1 d G . P A -1 C16 C 0.1888(5) 0.6516(12) 0.5617(14) 0.042(2) Uani 0.5 1 d G . P A -1 H16 H 0.212510 0.766597 0.495652 0.051 Uiso 0.5 1 calc R U P A -1 C17 C 0.1093(5) 0.6761(17) 0.5923(18) 0.057(3) Uani 0.5 1 d G . P A -1 H17 H 0.078692 0.807832 0.547176 0.068 Uiso 0.5 1 calc R U P A -1 C18 C 0.0746(4) 0.508(2) 0.6890(17) 0.055(2) Uani 0.5 1 d G . P A -1 H18 H 0.020230 0.524694 0.709925 0.066 Uiso 0.5 1 calc R U P A -1 C19 C 0.1193(3) 0.3153(15) 0.7551(13) 0.0525(19) Uani 0.5 1 d G . P A -1 H19 H 0.095584 0.200319 0.821151 0.063 Uiso 0.5 1 calc R U P A -1 C20 C 0.1988(3) 0.2908(11) 0.7245(10) 0.0421(16) Uani 0.5 1 d G . P A -1 H20 H 0.229403 0.159080 0.769629 0.050 Uiso 0.5 1 calc R U P A -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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0296(7) 0.0367(7) 0.0286(6) 0.0090(6) 0.0050(5) 0.0023(6) S2 0.0286(6) 0.0332(8) 0.0264(6) 0.0049(6) 0.0039(5) 0.0059(6) O1 0.0355(15) 0.0338(15) 0.0296(16) 0.0103(12) 0.0062(12) 0.0072(12) C1 0.0263(18) 0.034(2) 0.0161(19) 0.0014(18) 0.0011(15) 0.0045(17) C2 0.037(2) 0.026(2) 0.025(2) 0.004(2) 0.0034(18) 0.0079(18) C3 0.0330(17) 0.0326(19) 0.0175(18) 0.0057(15) 0.0006(15) 0.0053(14) C4 0.025(3) 0.028(3) 0.011(4) 0.001(3) -0.003(2) 0.002(2) C5 0.026(3) 0.032(3) 0.010(4) -0.002(2) -0.001(3) 0.001(2) C6 0.0350(18) 0.0322(19) 0.0165(18) -0.0001(15) 0.0027(16) 0.0063(14) C7 0.034(2) 0.029(2) 0.027(2) -0.0002(18) -0.0012(17) -0.0074(16) C8 0.0264(17) 0.033(2) 0.018(2) -0.0022(18) 0.0015(15) -0.0066(16) C9 0.0196(18) 0.062(4) 0.016(2) -0.011(3) -0.0048(17) -0.004(2) C10 0.033(3) 0.078(5) 0.015(3) -0.010(3) 0.003(2) 0.014(2) C11 0.031(3) 0.116(6) 0.015(3) -0.003(3) 0.003(3) 0.016(3) C12 0.027(3) 0.129(6) 0.023(5) 0.005(4) 0.000(3) 0.007(3) C13 0.018(3) 0.118(5) 0.023(3) 0.011(3) -0.005(3) -0.006(3) C14 0.018(3) 0.080(4) 0.026(3) 0.003(3) -0.004(3) -0.006(3) C15 0.024(2) 0.060(4) 0.017(2) -0.016(3) 0.0005(19) -0.005(2) C16 0.032(3) 0.074(4) 0.022(3) -0.009(3) 0.011(2) 0.008(2) C17 0.031(3) 0.117(6) 0.023(5) 0.004(4) 0.009(3) 0.017(3) C18 0.022(3) 0.126(6) 0.017(3) -0.002(4) -0.003(3) 0.001(3) C19 0.018(3) 0.115(5) 0.024(3) 0.001(3) -0.003(3) -0.010(3) C20 0.017(3) 0.084(4) 0.023(3) 0.001(3) -0.007(2) -0.012(3) 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' 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 S1 C1 91.0(4) . . ? C5 S2 C8 91.1(4) . . ? C6 O1 C3 103.5(3) . . ? C2 C1 S1 112.2(4) . . ? C2 C1 C9 127.5(5) . . ? C9 C1 S1 120.2(4) . . ? C1 C2 H2 125.6 . . ? C3 C2 C1 108.8(5) . . ? C3 C2 H2 125.6 . . ? O1 C3 C2 129.9(4) . . ? C4 C3 O1 112.6(6) . . ? C4 C3 C2 117.5(6) . . ? C3 C4 S1 110.5(7) . . ? C3 C4 C5 105.8(6) . . ? C5 C4 S1 143.6(4) . . ? C4 C5 S2 145.0(5) . . ? C6 C5 S2 110.3(7) . . ? C6 C5 C4 104.6(6) . . ? O1 C6 C5 113.5(6) . . ? O1 C6 C7 130.2(4) . . ? C5 C6 C7 116.3(6) . . ? C6 C7 H7 125.6 . . ? C8 C7 C6 108.9(5) . . ? C8 C7 H7 125.6 . . ? C7 C8 S2 113.3(4) . . ? C7 C8 C15 127.1(5) . . ? C15 C8 S2 119.5(4) . . ? C10 C9 C1 120.0(4) . . ? C10 C9 C14 120.0 . . ? C14 C9 C1 119.9(4) . . ? C9 C10 H10 120.0 . . ? C11 C10 C9 120.0 . . ? C11 C10 H10 120.0 . . ? C10 C11 H11 120.0 . . ? C10 C11 C12 120.0 . . ? C12 C11 H11 120.0 . . ? C11 C12 H12 120.0 . . ? C13 C12 C11 120.0 . . ? C13 C12 H12 120.0 . . ? C12 C13 H13 120.0 . . ? C14 C13 C12 120.0 . . ? C14 C13 H13 120.0 . . ? C9 C14 H14 120.0 . . ? C13 C14 C9 120.0 . . ? C13 C14 H14 120.0 . . ? C16 C15 C8 120.7(4) . . ? C16 C15 C20 120.0 . . ? C20 C15 C8 119.3(4) . . ? C15 C16 H16 120.0 . . ? C15 C16 C17 120.0 . . ? C17 C16 H16 120.0 . . ? C16 C17 H17 120.0 . . ? C18 C17 C16 120.0 . . ? C18 C17 H17 120.0 . . ? C17 C18 H18 120.0 . . ? C17 C18 C19 120.0 . . ? C19 C18 H18 120.0 . . ? C18 C19 H19 120.0 . . ? C20 C19 C18 120.0 . . ? C20 C19 H19 120.0 . . ? C15 C20 H20 120.0 . . ? C19 C20 C15 120.0 . . ? C19 C20 H20 120.0 . . ? 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 C1 1.754(5) . ? S1 C4 1.712(11) . ? S2 C5 1.723(11) . ? S2 C8 1.746(5) . ? O1 C3 1.378(5) . ? O1 C6 1.367(5) . ? C1 C2 1.417(7) . ? C1 C9 1.487(6) . ? C2 H2 0.9500 . ? C2 C3 1.379(7) . ? C3 C4 1.374(10) . ? C4 C5 1.434(5) . ? C5 C6 1.380(11) . ? C6 C7 1.411(7) . ? C7 H7 0.9500 . ? C7 C8 1.392(7) . ? C8 C15 1.492(6) . ? C9 C10 1.3900 . ? C9 C14 1.3900 . ? C10 H10 0.9500 . ? C10 C11 1.3900 . ? C11 H11 0.9500 . ? C11 C12 1.3900 . ? C12 H12 0.9500 . ? C12 C13 1.3900 . ? C13 H13 0.9500 . ? C13 C14 1.3900 . ? C14 H14 0.9500 . ? C15 C16 1.3900 . ? C15 C20 1.3900 . ? C16 H16 0.9500 . ? C16 C17 1.3900 . ? C17 H17 0.9500 . ? C17 C18 1.3900 . ? C18 H18 0.9500 . ? C18 C19 1.3900 . ? C19 H19 0.9500 . ? C19 C20 1.3900 . ? C20 H20 0.9500 . ? 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 S1 C1 C2 C3 -1.0(5) . . . . ? S1 C1 C9 C10 176.2(5) . . . . ? S1 C1 C9 C14 -0.1(7) . . . . ? S1 C4 C5 S2 0.3(12) . . . . ? S1 C4 C5 C6 -176.8(7) . . . . ? S2 C5 C6 O1 -179.0(3) . . . . ? S2 C5 C6 C7 1.3(7) . . . . ? S2 C8 C15 C16 2.3(7) . . . . ? S2 C8 C15 C20 -176.9(4) . . . . ? O1 C3 C4 S1 178.5(3) . . . . ? O1 C3 C4 C5 0.5(6) . . . . ? O1 C6 C7 C8 178.8(4) . . . . ? C1 S1 C4 C3 -0.3(5) . . . . ? C1 S1 C4 C5 176.6(7) . . . . ? C1 C2 C3 O1 -177.7(4) . . . . ? C1 C2 C3 C4 0.9(7) . . . . ? C1 C9 C10 C11 -176.3(7) . . . . ? C1 C9 C14 C13 176.3(7) . . . . ? C2 C1 C9 C10 -6.3(8) . . . . ? C2 C1 C9 C14 177.4(5) . . . . ? C2 C3 C4 S1 -0.3(7) . . . . ? C2 C3 C4 C5 -178.4(4) . . . . ? C3 O1 C6 C5 1.0(5) . . . . ? C3 O1 C6 C7 -179.3(5) . . . . ? C3 C4 C5 S2 177.2(8) . . . . ? C3 C4 C5 C6 0.1(5) . . . . ? C4 S1 C1 C2 0.8(4) . . . . ? C4 S1 C1 C9 178.6(5) . . . . ? C4 C5 C6 O1 -0.8(6) . . . . ? C4 C5 C6 C7 179.5(4) . . . . ? C5 S2 C8 C7 -0.3(4) . . . . ? C5 S2 C8 C15 -177.3(5) . . . . ? C5 C6 C7 C8 -1.5(6) . . . . ? C6 O1 C3 C2 177.8(5) . . . . ? C6 O1 C3 C4 -0.9(5) . . . . ? C6 C7 C8 S2 1.0(5) . . . . ? C6 C7 C8 C15 177.7(5) . . . . ? C7 C8 C15 C16 -174.2(6) . . . . ? C7 C8 C15 C20 6.6(8) . . . . ? C8 S2 C5 C4 -177.5(7) . . . . ? C8 S2 C5 C6 -0.5(5) . . . . ? C8 C15 C16 C17 -179.2(7) . . . . ? C8 C15 C20 C19 179.2(7) . . . . ? C9 C1 C2 C3 -178.7(5) . . . . ? C9 C10 C11 C12 0.0 . . . . ? C10 C9 C14 C13 0.0 . . . . ? C10 C11 C12 C13 0.0 . . . . ? C11 C12 C13 C14 0.0 . . . . ? C12 C13 C14 C9 0.0 . . . . ? C14 C9 C10 C11 0.0 . . . . ? C15 C16 C17 C18 0.0 . . . . ? C16 C15 C20 C19 0.0 . . . . ? C16 C17 C18 C19 0.0 . . . . ? C17 C18 C19 C20 0.0 . . . . ? C18 C19 C20 C15 0.0 . . . . ? C20 C15 C16 C17 0.0 . . . . ?