#------------------------------------------------------------------------------ #$Date: 2024-09-06 02:49:27 +0300 (Fri, 06 Sep 2024) $ #$Revision: 294476 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/21/1572156.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_1572156 loop_ _publ_author_name 'Chi, Zhuomin' 'Zhou, Yongchao' 'Liu, Bingbing' 'Xu, Xiaojing' 'Liu, Xueyuan' 'Liang, Yongmin' _publ_section_title ; Nickel-catalyzed regiodivergent sulfonylarylation of 1,3-enynes to access allenes and dienes. ; _journal_issue 33 _journal_name_full 'Chemical science' _journal_page_first 13271 _journal_page_last 13278 _journal_paper_doi 10.1039/d4sc03067b _journal_volume 15 _journal_year 2024 _chemical_formula_moiety 'C18 H18 O2 S' _chemical_formula_sum 'C18 H18 O2 S' _chemical_formula_weight 298.38 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2024-03-29 _audit_creation_method ; Olex2 1.5 (compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928) ; _audit_update_record ; 2024-03-29 deposited with the CCDC. 2024-07-23 downloaded from the CCDC. ; _cell_angle_alpha 66.4462(15) _cell_angle_beta 78.6780(13) _cell_angle_gamma 73.4692(12) _cell_formula_units_Z 2 _cell_length_a 9.12295(12) _cell_length_b 9.29509(14) _cell_length_c 10.32066(17) _cell_measurement_reflns_used 11872 _cell_measurement_temperature 150.00(10) _cell_measurement_theta_max 76.9700 _cell_measurement_theta_min 4.6630 _cell_volume 765.70(2) _computing_cell_refinement 'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)' _computing_data_collection 'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)' _computing_data_reduction 'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'SHELXT (Sheldrick, 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 150.00(10) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 0.988 _diffrn_measured_fraction_theta_max 0.988 _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 113.00 138.00 0.50 0.05 -- 64.00 77.00 104.06 50 2 \w 38.00 64.00 0.50 0.05 -- 64.00 77.00 104.06 52 3 \w 34.00 67.00 0.50 0.05 -- 60.00 77.00 -20.60 66 4 \w 47.00 73.00 0.50 0.05 -- 72.00 77.00 -23.20 52 5 \w 46.00 72.00 0.50 0.05 -- 72.00 77.00 -61.34 52 6 \w 85.00 170.00 0.50 0.05 -- 112.00 77.00 -60.00 170 7 \w 85.00 173.00 0.50 0.05 -- 112.00 77.00 0.00 176 8 \w 85.00 115.00 0.50 0.05 -- 112.00 77.00 30.00 60 9 \w 124.00 150.00 0.50 0.05 -- 112.00 77.00 120.00 52 10 \w 86.00 155.00 0.50 0.05 -- 112.00 77.00 150.00 138 11 \w 86.00 123.00 0.50 0.05 -- 112.00 77.00 120.00 74 12 \w 86.00 151.00 0.50 0.05 -- 112.00 77.00 90.00 130 13 \w 128.00 174.00 0.50 0.05 -- 112.00 77.00 -90.00 92 14 \w 85.00 117.00 0.50 0.05 -- 112.00 77.00 -90.00 64 15 \w 85.00 173.00 0.50 0.05 -- 112.00 77.00-150.00 176 16 \w 149.00 174.00 0.50 0.05 -- 112.00 77.00-180.00 50 17 \w 85.00 125.00 0.50 0.05 -- 112.00 77.00-180.00 80 18 \w 39.00 69.00 0.50 0.05 -- 64.00 76.00-149.70 60 19 \w 85.00 172.00 0.50 0.05 -- 112.00 77.00-120.00 174 20 \w 139.00 164.00 0.50 0.05 -- 112.00 77.00 30.00 50 21 \w 113.00 138.00 0.50 0.05 -- 64.00 75.00 158.68 50 22 \w 39.00 65.00 0.50 0.05 -- 64.00 75.00 158.68 52 23 \w 31.00 69.00 0.50 0.05 -- 56.00 76.00 31.98 76 24 \w 95.00 123.00 0.50 0.05 -- 112.00 61.00 90.00 56 25 \w 127.00 161.00 0.50 0.05 -- 112.00 61.00 -30.00 68 26 \w 112.00 138.00 0.50 0.05 -- 112.00 61.00 -60.00 52 27 \w 145.00 170.00 0.50 0.05 -- 112.00 45.00 -60.00 50 28 \w 94.00 153.00 0.50 0.05 -- 112.00 45.00-150.00 118 29 \w 33.00 69.00 0.50 0.05 -- 52.00 75.00 -93.22 72 30 \w 30.00 68.00 0.50 0.05 -- 56.00 75.00-174.76 76 31 \w 120.00 146.00 0.50 0.05 -- 112.00 45.00-180.00 52 32 \w 95.00 126.00 0.50 0.05 -- 112.00 45.00 -60.00 62 33 \w 93.00 171.00 0.50 0.05 -- 112.00 45.00 0.00 156 34 \w 126.00 175.00 0.50 0.05 -- 112.00 45.00 30.00 98 35 \w 95.00 122.00 0.50 0.05 -- 112.00 45.00 90.00 54 36 \w 127.00 164.00 0.50 0.05 -- 112.00 45.00 90.00 74 37 \w 96.00 166.00 0.50 0.05 -- 112.00 45.00 60.00 140 38 \w 86.00 134.00 0.50 0.05 -- 112.00 115.00 166.00 96 39 \w 80.00 173.00 0.50 0.05 -- 112.00 125.00 90.00 186 40 \w 90.00 115.00 0.50 0.05 -- 45.27 169.00 -49.00 50 41 \w 52.00 83.00 0.50 0.05 -- 45.27 169.00 -49.00 62 42 \w 97.00 123.00 0.50 0.05 -- 112.00 169.00 -49.00 52 43 \w 63.00 119.00 0.50 0.05 -- 45.27 77.00 90.00 112 44 \w 18.00 52.00 0.50 0.05 -- 45.27 77.00 90.00 68 45 \w 28.00 77.00 0.50 0.05 -- 45.27 57.00 30.00 98 46 \w 81.00 107.00 0.50 0.05 -- 45.27 57.00 30.00 52 47 \w 84.00 110.00 0.50 0.05 -- 45.27 37.00 0.00 52 48 \w 28.00 74.00 0.50 0.05 -- 45.27 37.00 0.00 92 49 \w 18.00 44.00 0.50 0.05 -- 45.27 77.00 -30.00 52 50 \w 26.00 68.00 0.50 0.05 -- 45.27 57.00-120.00 84 51 \w 19.00 44.00 0.50 0.05 -- 45.27 77.00-180.00 50 52 \w 40.00 68.00 0.50 0.05 -- 112.00 -61.00 -90.00 56 53 \w 39.00 67.00 0.50 0.05 -- 112.00 -61.00-120.00 56 54 \w 50.00 93.00 0.50 0.05 -- 112.00 -77.00-180.00 86 55 \w 59.00 90.00 0.50 0.05 -- 112.00 -77.00 -30.00 62 56 \w 43.00 68.00 0.50 0.05 -- 112.00 -61.00 0.00 50 57 \w 41.00 67.00 0.50 0.05 -- 112.00 -61.00 90.00 52 58 \w 43.00 98.00 0.50 0.05 -- 112.00 -77.00 120.00 110 59 \w 46.00 84.00 0.50 0.05 -- 112.00 -77.00 150.00 76 60 \w 39.00 65.00 0.50 0.05 -- 112.00 -94.00 120.00 52 61 \w 83.00 110.00 0.50 0.05 -- 112.00-125.00 30.00 54 62 \w 48.00 112.00 0.50 0.05 -- 112.00-125.00 0.00 128 63 \w 42.00 74.00 0.50 0.05 -- 112.00-125.00 30.00 64 64 \w 43.00 112.00 0.50 0.05 -- 112.00-125.00 120.00 138 65 \w 78.00 112.00 0.50 0.05 -- 112.00-125.00 60.00 68 66 \w 42.00 71.00 0.50 0.05 -- 112.00-125.00 60.00 58 67 \w 61.00 87.00 0.50 0.05 -- 112.00-115.00 76.00 52 68 \w 21.00 50.00 0.50 0.05 -- 45.27-115.00 76.00 58 69 \w 71.00 99.00 0.50 0.05 -- 112.00 -94.00 120.00 56 70 \w 56.00 81.00 0.50 0.05 -- 45.27-169.00 -67.00 50 71 \w 105.00 141.00 0.50 0.05 -- 112.00-169.00 -67.00 72 72 \w 42.00 73.00 0.50 0.05 -- 112.00-125.00-120.00 62 73 \w 55.00 81.00 0.50 0.05 -- 112.00 -94.00-120.00 52 74 \w 61.00 86.00 0.50 0.05 -- 112.00 -94.00 -90.00 50 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'ROD, Synergy Custom system, HyPix' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0588212000 _diffrn_orient_matrix_UB_12 -0.1549828000 _diffrn_orient_matrix_UB_13 0.0838459000 _diffrn_orient_matrix_UB_21 0.0166392000 _diffrn_orient_matrix_UB_22 -0.0327732000 _diffrn_orient_matrix_UB_23 -0.1377904000 _diffrn_orient_matrix_UB_31 0.1660355000 _diffrn_orient_matrix_UB_32 -0.0970027000 _diffrn_orient_matrix_UB_33 0.0271259000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0281 _diffrn_reflns_av_unetI/netI 0.0175 _diffrn_reflns_Laue_measured_fraction_full 0.988 _diffrn_reflns_Laue_measured_fraction_max 0.988 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 12187 _diffrn_reflns_point_group_measured_fraction_full 0.988 _diffrn_reflns_point_group_measured_fraction_max 0.988 _diffrn_reflns_theta_full 66.590 _diffrn_reflns_theta_max 66.590 _diffrn_reflns_theta_min 4.695 _diffrn_source 'Rotating-anode X-ray tube' _diffrn_source_type 'Rigaku (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 1.883 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.77624 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.294 _exptl_crystal_description block _exptl_crystal_F_000 316 _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.06 _refine_diff_density_max 0.318 _refine_diff_density_min -0.332 _refine_diff_density_rms 0.038 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 212 _refine_ls_number_reflns 2674 _refine_ls_number_restraints 61 _refine_ls_restrained_S_all 1.040 _refine_ls_R_factor_all 0.0317 _refine_ls_R_factor_gt 0.0313 _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^)+(0.0468P)^2^+0.2822P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0855 _refine_ls_wR_factor_ref 0.0859 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2616 _reflns_number_total 2674 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4sc03067b2.cif _cod_data_source_block chizhm_0104_auto _cod_depositor_comments 'Adding full bibliography for 1572156.cif.' _cod_database_code 1572156 _shelx_shelxl_version_number 2016/6 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2. Restrained distances C2-C10 1.54 with sigma of 0.02 C2-C10 \\sim C2A-C10 with sigma of 0.02 C10-C17 \\sim C10-C17A with sigma of 0.02 3. Rigid bond restraints All non-hydrogen atoms with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01 4. Uiso/Uaniso restraints and constraints C2 \\sim C17: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A 5. Others Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(H2AC)=Sof(C17A)=Sof(H17C)=Sof(H17D)=1-FVAR(1) Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(H2C)=Sof(C17)=Sof(H17A)=Sof(H17B)=FVAR(1) 6.a Aromatic/amide H refined with riding coordinates: C1(H1), C3(H3), C7(H7), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14), C16(H16), C18(H18) 6.b X=CH2 refined with riding coordinates: C17(H17A,H17B), C17A(H17C,H17D) 6.c Idealised Me refined as rotating group: C2(H2A,H2B,H2C), C15(H15A,H15B,H15C), C2A(H2AA,H2AB,H2AC) ; _shelx_res_file ; TITL chizhm_0104_auto_a.res in P-1 chizhm_0104_auto.res created by SHELXL-2016/6 at 17:03:55 on 29-Mar-2024 REM Old TITL chizhm_0104_auto in P-1 REM SHELXT solution in P-1: R1 0.117, Rweak 0.008, Alpha 0.055 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C18 O2 Cl CELL 1.54184 9.122952 9.295095 10.320661 66.4462 78.678 73.4692 ZERR 2 0.000124 0.000136 0.000168 0.0015 0.0013 0.0012 LATT 1 SFAC C H O S UNIT 36 36 4 2 DELU DFIX 1.54 C2 C10 SIMU 0.01 0.02 2 C2 C17 SADI C2 C10 C2A C10 SADI C10 C17 C10 C17A L.S. 20 0 0 PLAN 10 TEMP -123 CONF BOND list 4 MORE -1 BOND $H fmap 2 53 acta SHEL 999 0.84 OMIT 1 1 3 REM REM REM WGHT 0.046800 0.282200 FVAR 16.84426 0.62189 S1 4 0.162462 0.517761 0.252710 11.00000 0.02129 0.02583 = 0.02519 -0.00669 -0.00569 -0.00288 O1 3 0.219224 0.614185 0.113854 11.00000 0.03109 0.03396 = 0.02761 -0.00273 -0.00651 -0.00906 O2 3 0.047778 0.598012 0.334562 11.00000 0.02497 0.03084 = 0.03553 -0.01255 -0.00715 0.00047 C1 1 0.301771 0.389149 0.489583 11.00000 0.02212 0.02661 = 0.02973 -0.00947 -0.00331 -0.00457 AFIX 43 H1 2 0.204555 0.444342 0.519104 11.00000 -1.20000 AFIX 0 PART 1 C2 1 0.566786 0.414857 0.183920 21.00000 0.02565 0.04792 = 0.02921 -0.00686 0.00216 -0.00936 AFIX 137 H2A 2 0.513108 0.512574 0.112630 21.00000 -1.50000 H2B 2 0.644554 0.350456 0.136249 21.00000 -1.50000 H2C 2 0.616673 0.444917 0.242154 21.00000 -1.50000 AFIX 0 PART 0 C3 1 0.606247 0.153207 0.815797 11.00000 0.03997 0.02931 = 0.03531 -0.00595 -0.01736 -0.00559 AFIX 43 H3 2 0.672619 0.101913 0.889725 11.00000 -1.20000 AFIX 0 C4 1 0.320851 0.398880 0.354833 11.00000 0.02113 0.02373 = 0.02659 -0.00576 -0.00568 -0.00500 C5 1 -0.027117 0.138878 0.208049 11.00000 0.02282 0.02905 = 0.04319 -0.01271 -0.01304 0.00201 C6 1 0.411311 0.304331 0.598220 11.00000 0.02780 0.02280 = 0.02676 -0.00788 -0.00604 -0.00522 C7 1 0.449011 0.190696 0.848075 11.00000 0.04317 0.03984 = 0.02650 -0.00721 -0.00732 -0.00530 AFIX 43 H7 2 0.407236 0.164120 0.944364 11.00000 -1.20000 AFIX 0 C8 1 0.087698 0.371578 0.234403 11.00000 0.01920 0.02824 = 0.02791 -0.00878 -0.00698 -0.00135 C9 1 0.352075 0.267081 0.740080 11.00000 0.03015 0.03594 = 0.03059 -0.01073 -0.00412 -0.00341 AFIX 43 H9 2 0.244244 0.294292 0.762992 11.00000 -1.20000 AFIX 0 C10 1 0.450917 0.315590 0.279039 11.00000 0.02341 0.03270 = 0.02902 -0.01231 -0.00842 -0.00008 C11 1 0.063426 0.226930 0.096681 11.00000 0.03160 0.03651 = 0.03137 -0.01426 -0.01031 -0.00083 AFIX 43 H11 2 0.085787 0.207087 0.010642 11.00000 -1.20000 AFIX 0 C12 1 -0.001817 0.285048 0.347915 11.00000 0.02709 0.03482 = 0.02998 -0.01197 -0.00147 -0.00582 AFIX 43 H12 2 -0.023791 0.304812 0.433982 11.00000 -1.20000 AFIX 0 C13 1 0.666623 0.190550 0.675689 11.00000 0.02810 0.03329 = 0.03956 -0.00856 -0.01047 -0.00759 AFIX 43 H13 2 0.774694 0.164944 0.653505 11.00000 -1.20000 AFIX 0 C14 1 0.121568 0.342700 0.108525 11.00000 0.02671 0.03451 = 0.02691 -0.00887 -0.00564 -0.00389 AFIX 43 H14 2 0.183727 0.401609 0.031777 11.00000 -1.20000 AFIX 0 C15 1 -0.090353 0.014073 0.192230 11.00000 0.03864 0.03762 = 0.06223 -0.02175 -0.01472 -0.00606 AFIX 137 H15A 2 -0.151991 0.064884 0.110950 11.00000 -1.50000 H15B 2 -0.154884 -0.032425 0.278727 11.00000 -1.50000 H15C 2 -0.005274 -0.071339 0.176732 11.00000 -1.50000 AFIX 0 C16 1 0.570342 0.265193 0.567289 11.00000 0.02761 0.03352 = 0.02932 -0.00840 -0.00534 -0.00845 AFIX 43 H16 2 0.612882 0.289871 0.471314 11.00000 -1.20000 AFIX 0 PART 1 C17 1 0.461686 0.169044 0.289877 21.00000 0.03076 0.03808 = 0.06933 -0.02751 -0.01040 0.00020 AFIX 93 H17A 2 0.385634 0.112749 0.347061 21.00000 -1.20000 H17B 2 0.545621 0.118058 0.240627 21.00000 -1.20000 AFIX 0 PART 0 C18 1 -0.058356 0.169633 0.333369 11.00000 0.02568 0.03324 = 0.03844 -0.00924 -0.00141 -0.00751 AFIX 43 H18 2 -0.119766 0.110109 0.410452 11.00000 -1.20000 AFIX 0 PART 2 C2A 1 0.459060 0.133205 0.335946 -21.00000 0.04886 0.02409 = 0.05599 -0.01740 -0.01178 0.00620 AFIX 137 H2AA 2 0.542964 0.081983 0.281945 -21.00000 -1.50000 H2AB 2 0.361711 0.115620 0.325634 -21.00000 -1.50000 H2AC 2 0.477682 0.086011 0.436453 -21.00000 -1.50000 AFIX 0 C17A 1 0.538323 0.386750 0.177105 -21.00000 0.02878 0.04389 = 0.04031 -0.01365 -0.00242 0.00023 AFIX 93 H17C 2 0.522975 0.500626 0.144308 -21.00000 -1.20000 H17D 2 0.619425 0.326405 0.133218 -21.00000 -1.20000 AFIX 0 HKLF 4 REM chizhm_0104_auto_a.res in P-1 REM R1 = 0.0313 for 2616 Fo > 4sig(Fo) and 0.0317 for all 2674 data REM 212 parameters refined using 61 restraints END WGHT 0.0468 0.2821 REM Highest difference peak 0.318, deepest hole -0.332, 1-sigma level 0.038 Q1 1 0.1213 0.4406 0.2445 11.00000 0.05 0.32 Q2 1 0.2474 0.4601 0.3055 11.00000 0.05 0.32 Q3 1 0.3781 0.3749 0.3005 11.00000 0.05 0.20 Q4 1 0.3707 0.3380 0.5456 11.00000 0.05 0.19 Q5 1 0.0810 0.3840 0.1700 11.00000 0.05 0.17 Q6 1 -0.2047 0.0348 0.1994 11.00000 0.05 0.16 Q7 1 0.6140 0.2426 0.6263 11.00000 0.05 0.16 Q8 1 0.1457 0.3287 0.1996 11.00000 0.05 0.16 Q9 1 0.0661 0.3161 0.2968 11.00000 0.05 0.16 Q10 1 0.0614 0.6023 0.2633 11.00000 0.05 0.16 ; _shelx_res_checksum 45253 _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 1.709 _oxdiff_exptl_absorpt_empirical_full_min 0.336 loop_ _space_group_symop_operation_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_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 0.16246(3) 0.51776(4) 0.25271(3) 0.02500(13) Uani 1 1 d . U . . . O1 O 0.21922(11) 0.61419(12) 0.11385(10) 0.0328(2) Uani 1 1 d . U . . . O2 O 0.04778(11) 0.59801(12) 0.33456(11) 0.0312(2) Uani 1 1 d . U . . . C1 C 0.30177(15) 0.38915(16) 0.48958(14) 0.0265(3) Uani 1 1 d . U . . . H1 H 0.204555 0.444342 0.519104 0.032 Uiso 1 1 calc R U . . . C2 C 0.5668(10) 0.4149(11) 0.1839(8) 0.0371(14) Uani 0.622(16) 1 d D U P A 1 H2A H 0.513108 0.512574 0.112630 0.056 Uiso 0.622(16) 1 calc R U P A 1 H2B H 0.644554 0.350456 0.136249 0.056 Uiso 0.622(16) 1 calc R U P A 1 H2C H 0.616673 0.444917 0.242154 0.056 Uiso 0.622(16) 1 calc R U P A 1 C3 C 0.60625(19) 0.15321(18) 0.81580(16) 0.0352(3) Uani 1 1 d . U . . . H3 H 0.672619 0.101913 0.889725 0.042 Uiso 1 1 calc R U . . . C4 C 0.32085(15) 0.39888(15) 0.35483(14) 0.0245(3) Uani 1 1 d . U . . . C5 C -0.02712(16) 0.13888(17) 0.20805(17) 0.0321(3) Uani 1 1 d . U . . . C6 C 0.41131(16) 0.30433(16) 0.59822(14) 0.0258(3) Uani 1 1 d . U . . . C7 C 0.44901(19) 0.19070(19) 0.84808(16) 0.0384(4) Uani 1 1 d . U . . . H7 H 0.407236 0.164120 0.944364 0.046 Uiso 1 1 calc R U . . . C8 C 0.08770(15) 0.37158(16) 0.23440(14) 0.0258(3) Uani 1 1 d . U . . . C9 C 0.35207(18) 0.26708(18) 0.74008(16) 0.0334(3) Uani 1 1 d . U . . . H9 H 0.244244 0.294292 0.762992 0.040 Uiso 1 1 calc R U . . . C10 C 0.45092(16) 0.31559(17) 0.27904(15) 0.0286(3) Uani 1 1 d D U . . . C11 C 0.06343(17) 0.22693(18) 0.09668(16) 0.0330(3) Uani 1 1 d . U . . . H11 H 0.085787 0.207087 0.010642 0.040 Uiso 1 1 calc R U . . . C12 C -0.00182(16) 0.28505(18) 0.34791(15) 0.0311(3) Uani 1 1 d . U . . . H12 H -0.023791 0.304812 0.433982 0.037 Uiso 1 1 calc R U . . . C13 C 0.66662(17) 0.19055(18) 0.67569(16) 0.0340(3) Uani 1 1 d . U . . . H13 H 0.774694 0.164944 0.653505 0.041 Uiso 1 1 calc R U . . . C14 C 0.12157(16) 0.34270(18) 0.10852(15) 0.0304(3) Uani 1 1 d . U . . . H14 H 0.183727 0.401609 0.031777 0.036 Uiso 1 1 calc R U . . . C15 C -0.0904(2) 0.0141(2) 0.1922(2) 0.0441(4) Uani 1 1 d . U . . . H15A H -0.151991 0.064884 0.110950 0.066 Uiso 1 1 calc R U . . . H15B H -0.154884 -0.032425 0.278727 0.066 Uiso 1 1 calc R U . . . H15C H -0.005274 -0.071339 0.176732 0.066 Uiso 1 1 calc R U . . . C16 C 0.57034(16) 0.26519(17) 0.56729(15) 0.0304(3) Uani 1 1 d . U . . . H16 H 0.612882 0.289871 0.471314 0.037 Uiso 1 1 calc R U . . . C17 C 0.4617(11) 0.1690(10) 0.2899(10) 0.0444(16) Uani 0.622(16) 1 d D U P A 1 H17A H 0.385634 0.112749 0.347061 0.053 Uiso 0.622(16) 1 calc R U P A 1 H17B H 0.545621 0.118058 0.240627 0.053 Uiso 0.622(16) 1 calc R U P A 1 C18 C -0.05836(17) 0.16963(18) 0.33337(17) 0.0338(3) Uani 1 1 d . U . . . H18 H -0.119766 0.110109 0.410452 0.041 Uiso 1 1 calc R U . . . C2A C 0.459(2) 0.1332(14) 0.3359(14) 0.044(2) Uani 0.378(16) 1 d D U P A 2 H2AA H 0.542964 0.081983 0.281945 0.066 Uiso 0.378(16) 1 calc R U P A 2 H2AB H 0.361711 0.115620 0.325634 0.066 Uiso 0.378(16) 1 calc R U P A 2 H2AC H 0.477682 0.086011 0.436453 0.066 Uiso 0.378(16) 1 calc R U P A 2 C17A C 0.5383(17) 0.3867(19) 0.1771(14) 0.040(2) Uani 0.378(16) 1 d D U P A 2 H17C H 0.522975 0.500626 0.144308 0.048 Uiso 0.378(16) 1 calc R U P A 2 H17D H 0.619425 0.326405 0.133218 0.048 Uiso 0.378(16) 1 calc R U P A 2 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 0.02129(19) 0.02583(19) 0.02519(19) -0.00669(14) -0.00569(13) -0.00288(13) O1 0.0311(5) 0.0340(5) 0.0276(5) -0.0027(4) -0.0065(4) -0.0091(4) O2 0.0250(5) 0.0308(5) 0.0355(6) -0.0125(4) -0.0072(4) 0.0005(4) C1 0.0221(7) 0.0266(7) 0.0297(7) -0.0095(6) -0.0033(5) -0.0046(5) C2 0.026(3) 0.048(3) 0.0292(18) -0.0069(17) 0.0022(16) -0.0094(16) C3 0.0400(8) 0.0293(7) 0.0353(8) -0.0060(6) -0.0174(7) -0.0056(6) C4 0.0211(6) 0.0237(6) 0.0266(7) -0.0058(5) -0.0057(5) -0.0050(5) C5 0.0228(7) 0.0290(7) 0.0432(8) -0.0127(6) -0.0130(6) 0.0020(6) C6 0.0278(7) 0.0228(6) 0.0268(7) -0.0079(5) -0.0060(5) -0.0052(5) C7 0.0432(9) 0.0398(8) 0.0265(7) -0.0072(6) -0.0073(6) -0.0053(7) C8 0.0192(6) 0.0282(7) 0.0279(7) -0.0088(6) -0.0070(5) -0.0014(5) C9 0.0301(8) 0.0359(8) 0.0306(7) -0.0107(6) -0.0041(6) -0.0034(6) C10 0.0234(7) 0.0327(8) 0.0290(7) -0.0123(6) -0.0084(6) -0.0001(6) C11 0.0316(8) 0.0365(8) 0.0314(7) -0.0143(6) -0.0103(6) -0.0008(6) C12 0.0271(7) 0.0348(8) 0.0300(7) -0.0120(6) -0.0015(6) -0.0058(6) C13 0.0281(7) 0.0333(8) 0.0396(8) -0.0086(6) -0.0105(6) -0.0076(6) C14 0.0267(7) 0.0345(8) 0.0269(7) -0.0089(6) -0.0056(6) -0.0039(6) C15 0.0386(9) 0.0376(9) 0.0622(11) -0.0217(8) -0.0147(8) -0.0061(7) C16 0.0276(7) 0.0335(7) 0.0293(7) -0.0084(6) -0.0053(6) -0.0084(6) C17 0.0308(18) 0.038(3) 0.069(5) -0.028(3) -0.010(3) 0.000(2) C18 0.0257(7) 0.0332(8) 0.0384(8) -0.0092(6) -0.0014(6) -0.0075(6) C2A 0.049(4) 0.024(4) 0.056(6) -0.017(4) -0.012(5) 0.006(3) C17A 0.029(5) 0.044(5) 0.040(3) -0.014(3) -0.002(3) 0.000(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 '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 O1 S1 O2 118.36(6) . . ? O1 S1 C4 109.01(6) . . ? O1 S1 C8 108.10(6) . . ? O2 S1 C4 109.22(6) . . ? O2 S1 C8 108.03(6) . . ? C8 S1 C4 103.03(6) . . ? C4 C1 H1 115.7 . . ? C4 C1 C6 128.59(13) . . ? C6 C1 H1 115.7 . . ? H2A C2 H2B 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C10 C2 H2A 109.5 . . ? C10 C2 H2B 109.5 . . ? C10 C2 H2C 109.5 . . ? C7 C3 H3 120.1 . . ? C13 C3 H3 120.1 . . ? C13 C3 C7 119.82(14) . . ? C1 C4 S1 115.83(10) . . ? C1 C4 C10 129.59(12) . . ? C10 C4 S1 114.42(9) . . ? C11 C5 C15 120.43(14) . . ? C11 C5 C18 118.41(14) . . ? C18 C5 C15 121.16(14) . . ? C9 C6 C1 117.56(12) . . ? C9 C6 C16 118.53(13) . . ? C16 C6 C1 123.86(12) . . ? C3 C7 H7 119.9 . . ? C3 C7 C9 120.12(14) . . ? C9 C7 H7 119.9 . . ? C12 C8 S1 119.17(11) . . ? C14 C8 S1 119.77(11) . . ? C14 C8 C12 121.05(13) . . ? C6 C9 H9 119.7 . . ? C7 C9 C6 120.69(14) . . ? C7 C9 H9 119.7 . . ? C4 C10 C2 116.3(4) . . ? C4 C10 C2A 111.1(6) . . ? C17 C10 C2 122.4(5) . . ? C17 C10 C4 121.3(4) . . ? C17A C10 C4 124.2(7) . . ? C17A C10 C2A 124.6(9) . . ? C5 C11 H11 119.3 . . ? C14 C11 C5 121.38(14) . . ? C14 C11 H11 119.3 . . ? C8 C12 H12 120.6 . . ? C18 C12 C8 118.83(13) . . ? C18 C12 H12 120.6 . . ? C3 C13 H13 119.8 . . ? C3 C13 C16 120.37(14) . . ? C16 C13 H13 119.8 . . ? C8 C14 H14 120.5 . . ? C11 C14 C8 118.96(13) . . ? C11 C14 H14 120.5 . . ? C5 C15 H15A 109.5 . . ? C5 C15 H15B 109.5 . . ? C5 C15 H15C 109.5 . . ? H15A C15 H15B 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C6 C16 H16 119.8 . . ? C13 C16 C6 120.46(14) . . ? C13 C16 H16 119.8 . . ? C10 C17 H17A 120.0 . . ? C10 C17 H17B 120.0 . . ? H17A C17 H17B 120.0 . . ? C5 C18 H18 119.3 . . ? C12 C18 C5 121.37(14) . . ? C12 C18 H18 119.3 . . ? C10 C2A H2AA 109.5 . . ? C10 C2A H2AB 109.5 . . ? C10 C2A H2AC 109.5 . . ? H2AA C2A H2AB 109.5 . . ? H2AA C2A H2AC 109.5 . . ? H2AB C2A H2AC 109.5 . . ? C10 C17A H17C 120.0 . . ? C10 C17A H17D 120.0 . . ? H17C C17A H17D 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 O1 1.4392(10) . ? S1 O2 1.4412(10) . ? S1 C4 1.7828(13) . ? S1 C8 1.7693(14) . ? C1 H1 0.9500 . ? C1 C4 1.336(2) . ? C1 C6 1.4705(19) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C2 C10 1.535(7) . ? C3 H3 0.9500 . ? C3 C7 1.382(2) . ? C3 C13 1.382(2) . ? C4 C10 1.4886(19) . ? C5 C11 1.390(2) . ? C5 C15 1.508(2) . ? C5 C18 1.393(2) . ? C6 C9 1.395(2) . ? C6 C16 1.396(2) . ? C7 H7 0.9500 . ? C7 C9 1.388(2) . ? C8 C12 1.3897(19) . ? C8 C14 1.389(2) . ? C9 H9 0.9500 . ? C10 C17 1.298(8) . ? C10 C2A 1.541(11) . ? C10 C17A 1.263(12) . ? C11 H11 0.9500 . ? C11 C14 1.382(2) . ? C12 H12 0.9500 . ? C12 C18 1.383(2) . ? C13 H13 0.9500 . ? C13 C16 1.387(2) . ? C14 H14 0.9500 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16 0.9500 . ? C17 H17A 0.9500 . ? C17 H17B 0.9500 . ? C18 H18 0.9500 . ? C2A H2AA 0.9800 . ? C2A H2AB 0.9800 . ? C2A H2AC 0.9800 . ? C17A H17C 0.9500 . ? C17A H17D 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 C4 C10 C2 84.4(4) . . . . ? S1 C4 C10 C17 -93.4(5) . . . . ? S1 C4 C10 C2A -106.9(6) . . . . ? S1 C4 C10 C17A 70.0(8) . . . . ? S1 C8 C12 C18 -179.25(11) . . . . ? S1 C8 C14 C11 179.35(10) . . . . ? O1 S1 C4 C1 137.60(11) . . . . ? O1 S1 C4 C10 -46.55(11) . . . . ? O1 S1 C8 C12 -166.99(11) . . . . ? O1 S1 C8 C14 14.28(13) . . . . ? O2 S1 C4 C1 6.90(13) . . . . ? O2 S1 C4 C10 -177.25(9) . . . . ? O2 S1 C8 C12 -37.81(12) . . . . ? O2 S1 C8 C14 143.47(11) . . . . ? C1 C4 C10 C2 -100.4(4) . . . . ? C1 C4 C10 C17 81.8(5) . . . . ? C1 C4 C10 C2A 68.2(6) . . . . ? C1 C4 C10 C17A -114.8(9) . . . . ? C1 C6 C9 C7 -178.41(14) . . . . ? C1 C6 C16 C13 177.48(13) . . . . ? C3 C7 C9 C6 1.2(2) . . . . ? C3 C13 C16 C6 0.3(2) . . . . ? C4 S1 C8 C12 77.70(12) . . . . ? C4 S1 C8 C14 -101.03(12) . . . . ? C4 C1 C6 C9 -159.70(14) . . . . ? C4 C1 C6 C16 23.0(2) . . . . ? C5 C11 C14 C8 -0.3(2) . . . . ? C6 C1 C4 S1 -178.50(11) . . . . ? C6 C1 C4 C10 6.4(2) . . . . ? C7 C3 C13 C16 -0.1(2) . . . . ? C8 S1 C4 C1 -107.75(11) . . . . ? C8 S1 C4 C10 68.10(11) . . . . ? C8 C12 C18 C5 0.1(2) . . . . ? C9 C6 C16 C13 0.2(2) . . . . ? C11 C5 C18 C12 0.2(2) . . . . ? C12 C8 C14 C11 0.7(2) . . . . ? C13 C3 C7 C9 -0.6(2) . . . . ? C14 C8 C12 C18 -0.5(2) . . . . ? C15 C5 C11 C14 179.50(13) . . . . ? C15 C5 C18 C12 -179.38(14) . . . . ? C16 C6 C9 C7 -0.9(2) . . . . ? C18 C5 C11 C14 -0.1(2) . . . . ?