#------------------------------------------------------------------------------ #$Date: 2021-09-22 03:33:27 +0300 (Wed, 22 Sep 2021) $ #$Revision: 269236 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/83/7158308.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_7158308 loop_ _publ_author_name 'Zeng, Wenlei' 'Yu, Aimin' 'Meng, Xiangtai' _publ_section_title ; Catalyst-controlled switchable [4+1], [4+3] and [3+2] domino reactions of azadiene and MBH carbonate: diverse synthesis of benzothiophene fused derivatives ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D1OB01702K _journal_year 2021 _chemical_formula_moiety 'C36 H29 Cl N2 O5 S2' _chemical_formula_sum 'C36 H30 Cl N2 O5 S2' _chemical_formula_weight 670.19 _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 dual _audit_creation_date 2019-06-15 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2021-06-27 deposited with the CCDC. 2021-09-20 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 97.4240(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.39340(10) _cell_length_b 18.0084(3) _cell_length_c 17.5835(3) _cell_measurement_reflns_used 8153 _cell_measurement_temperature 179.98(10) _cell_measurement_theta_max 75.5550 _cell_measurement_theta_min 4.2850 _cell_volume 3263.49(8) _computing_cell_refinement 'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)' _computing_data_collection 'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)' _computing_data_reduction 'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 179.98(10) _diffrn_detector 'CCD plate' _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.970 _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 53.00 80.00 0.50 5.00 -- 109.88 -71.00 17.00 54 2 \w 84.00 132.00 0.50 5.00 -- 109.88 -71.00 17.00 96 3 \w 74.00 107.00 0.50 5.00 -- 109.88 -94.00 -30.00 66 4 \w 51.00 120.00 0.50 5.00 -- 109.88-125.00 0.00 138 5 \w 41.00 81.00 0.50 5.00 -- 109.88 -94.00 -60.00 80 6 \w 37.00 92.00 0.50 5.00 -- 109.88 -94.00-120.00 110 7 \w -4.00 21.00 0.50 2.00 -- 43.18 -71.00 17.00 50 8 \w 37.00 92.00 0.50 5.00 -- 109.88 -94.00 150.00 110 9 \w 90.00 178.00 0.50 5.00 -- 109.88 45.00 90.00 176 10 \w 87.00 177.00 0.50 5.00 -- 109.88 71.00 148.00 180 11 \w 89.00 178.00 0.50 5.00 -- 109.88 61.00-180.00 178 12 \w -68.00 29.00 0.50 2.00 -- -43.18 71.00 148.00 194 13 \w -91.00 -66.00 0.50 5.00 -- -90.25 71.00 148.00 50 14 \w -94.00 -59.00 0.50 5.00 -- -90.25 125.00 60.00 70 15 \w -81.00 -49.00 0.50 5.00 -- -90.25 125.00-180.00 64 16 \w -104.00 -17.00 0.50 2.00 -- -43.18 -71.00 17.00 174 17 \w -116.00 -71.00 0.50 2.00 -- -43.18-125.00 150.00 90 18 \w -110.00 -70.00 0.50 2.00 -- -43.18-125.00 120.00 80 19 \w -139.00-113.00 0.50 5.00 -- -90.25 -71.00 17.00 52 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy, Dualflex, HyPix' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0771600000 _diffrn_orient_matrix_UB_12 -0.0083603000 _diffrn_orient_matrix_UB_13 -0.0686550000 _diffrn_orient_matrix_UB_21 -0.0840115000 _diffrn_orient_matrix_UB_22 -0.0674353000 _diffrn_orient_matrix_UB_23 -0.0284476000 _diffrn_orient_matrix_UB_31 -0.0965747000 _diffrn_orient_matrix_UB_32 0.0519493000 _diffrn_orient_matrix_UB_33 -0.0478408000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0293 _diffrn_reflns_av_unetI/netI 0.0299 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.970 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 19995 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.970 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 75.911 _diffrn_reflns_theta_min 3.528 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 2.611 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.89113 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.34b (Rigaku Oxford Diffraction, 2017) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.364 _exptl_crystal_description block _exptl_crystal_F_000 1396 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _refine_diff_density_max 1.438 _refine_diff_density_min -0.431 _refine_diff_density_rms 0.057 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 418 _refine_ls_number_reflns 6586 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.058 _refine_ls_R_factor_all 0.0559 _refine_ls_R_factor_gt 0.0475 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0748P)^2^+1.8405P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1306 _refine_ls_wR_factor_ref 0.1393 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5608 _reflns_number_total 6586 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ob01702k2.cif _cod_data_source_block exp_2650 _cod_database_code 7158308 _shelx_shelxl_version_number 2017/1 _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 0.623 _shelx_estimated_absorpt_t_min 0.623 _reflns_odcompleteness_completeness 99.97 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _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.a Ternary CH refined with riding coordinates: C00D(H00D) 2.b Secondary CH2 refined with riding coordinates: C2(H2A,H2B) 2.c Aromatic/amide H refined with riding coordinates: C00K(H00K), C00N(H00N), C00P(H00P), C00Q(H00Q), C00R(H00R), C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z), C011(H011), C012(H012), C013(H013), C014(H014), C015(H015), C016(H016) 2.d Idealised Me refined as rotating group: C018(H01A,H01B,H01C), C01A(H01D,H01E,H01F), C3(H3A,H3B,H3C) ; _shelx_res_file ; TITL exp_2650_a.res in P2(1)/c exp_2650.res created by SHELXL-2017/1 at 23:01:59 on 15-Jun-2019 REM Old TITL exp_2650 in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.146, Rweak 0.010, Alpha 0.027 REM 0.612 for 231 systematic absences, Orientation as input REM Formula found by SHELXT: C36 N3 O4 Cl3 CELL 1.54184 10.3934 18.0084 17.5835 90 97.424 90 ZERR 4 0.0001 0.0003 0.0003 0 0.001 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H Cl N O S UNIT 144 120 4 8 20 8 L.S. 20 0 0 PLAN 20 SIZE 0.2 0.2 0.2 BOND list 4 fmap 2 53 acta OMIT 1 0 20 OMIT -7 7 17 OMIT -6 7 18 OMIT 10 7 8 OMIT -5 7 19 OMIT -4 7 19 REM REM REM WGHT 0.074800 1.840500 FVAR 0.28614 S01 6 0.054247 0.351237 0.437767 11.00000 0.03165 0.03822 = 0.03520 0.00751 0.00199 0.00158 S02 6 0.248850 0.200156 0.686083 11.00000 0.03038 0.04701 = 0.03191 0.00811 0.00162 -0.00171 CL03 3 -0.024634 0.077950 0.349181 11.00000 0.05624 0.08270 = 0.07025 -0.02737 -0.01048 -0.00254 O004 5 0.020809 0.297010 0.378701 11.00000 0.05268 0.04858 = 0.03674 0.00390 -0.00528 -0.00875 O005 5 -0.047845 0.382816 0.474365 11.00000 0.03681 0.04757 = 0.05874 0.01631 0.01386 0.00912 O006 5 0.544508 0.163343 0.647399 11.00000 0.03078 0.04777 = 0.05753 0.00596 -0.00124 0.00464 N007 4 0.170404 0.315259 0.498869 11.00000 0.03129 0.03422 = 0.03128 0.00287 0.00374 0.00302 O009 5 0.520276 0.158145 0.423452 11.00000 0.07658 0.03849 = 0.08633 -0.01068 0.04668 -0.00261 N00A 4 0.419613 0.068866 0.589907 11.00000 0.04400 0.03354 = 0.05046 0.00550 0.00798 0.00715 C00B 1 0.158704 0.270090 0.553888 11.00000 0.02741 0.03067 = 0.02976 -0.00340 0.00394 0.00190 C00C 1 0.333733 0.385320 0.635004 11.00000 0.02611 0.03922 = 0.03917 -0.00666 -0.00034 -0.00184 C00D 1 0.387817 0.310560 0.614506 11.00000 0.02733 0.03539 = 0.03805 0.00086 0.00156 -0.00022 AFIX 13 H00D 2 0.451489 0.295613 0.657829 11.00000 -1.20000 AFIX 0 C00E 1 0.359233 0.189905 0.548052 11.00000 0.02841 0.03236 = 0.03905 0.00221 0.00705 0.00200 C00F 1 0.138857 0.424199 0.399927 11.00000 0.03587 0.03825 = 0.03261 0.00610 0.00275 0.00064 C00G 1 0.273855 0.131868 0.504080 11.00000 0.03404 0.03295 = 0.04054 -0.00221 0.01185 0.00100 C00H 1 0.047885 0.236273 0.583486 11.00000 0.02844 0.03450 = 0.03235 -0.00054 0.00479 -0.00014 C00I 1 0.082467 0.199687 0.653435 11.00000 0.03087 0.03730 = 0.03138 -0.00296 0.00494 -0.00097 C00J 1 0.288535 0.245088 0.598957 11.00000 0.02752 0.03379 = 0.03137 0.00378 0.00343 0.00026 C00K 1 0.455264 0.307473 0.543785 11.00000 0.02983 0.03402 = 0.04726 0.00368 0.00985 0.00025 AFIX 43 H00K 2 0.504731 0.346273 0.528131 11.00000 -1.20000 AFIX 0 C00L 1 0.437045 0.244118 0.506282 11.00000 0.03234 0.03404 = 0.04397 0.00455 0.01250 0.00200 C00M 1 0.311823 0.062087 0.533467 11.00000 0.04337 0.03322 = 0.04612 -0.00036 0.01427 0.00029 C00N 1 -0.082864 0.236085 0.550940 11.00000 0.03063 0.04261 = 0.04253 0.00583 -0.00028 -0.00035 AFIX 43 H00N 2 -0.107609 0.258702 0.503768 11.00000 -1.20000 AFIX 0 C00O 1 0.455071 0.140450 0.601720 11.00000 0.03323 0.03683 = 0.04421 0.00543 0.01036 0.00474 C00P 1 0.171854 0.137624 0.445767 11.00000 0.04077 0.04096 = 0.04229 -0.00691 0.00847 0.00287 AFIX 43 H00P 2 0.147019 0.183321 0.423991 11.00000 -1.20000 AFIX 0 C00Q 1 -0.009713 0.165741 0.692073 11.00000 0.03858 0.05047 = 0.03461 0.00321 0.00838 -0.00632 AFIX 43 H00Q 2 0.014211 0.141975 0.738714 11.00000 -1.20000 AFIX 0 C00R 1 0.329981 0.445584 0.585638 11.00000 0.04465 0.04015 = 0.04198 -0.00445 0.00310 0.00507 AFIX 43 H00R 2 0.358065 0.439797 0.537870 11.00000 -1.20000 AFIX 0 C00S 1 0.495815 0.221640 0.437451 11.00000 0.04743 0.03884 = 0.05740 -0.00158 0.02158 -0.00044 C00T 1 0.260160 0.538774 0.331461 11.00000 0.04145 0.04940 = 0.03907 0.00749 -0.00243 -0.01049 C00U 1 0.088928 0.494910 0.400422 11.00000 0.04435 0.04098 = 0.05162 0.00608 0.01273 0.00254 AFIX 43 H00U 2 0.015020 0.504408 0.423521 11.00000 -1.20000 AFIX 0 C00V 1 -0.138252 0.168080 0.659541 11.00000 0.03590 0.05201 = 0.04958 0.00066 0.01379 -0.00657 AFIX 43 H00V 2 -0.201566 0.146424 0.685173 11.00000 -1.20000 AFIX 0 C00W 1 0.290691 0.395238 0.705716 11.00000 0.04498 0.04827 = 0.04334 -0.00653 0.00951 -0.00389 AFIX 43 H00W 2 0.293153 0.355761 0.739973 11.00000 -1.20000 AFIX 0 C00X 1 0.250172 0.409382 0.366246 11.00000 0.04477 0.04624 = 0.04430 0.00659 0.01066 0.00555 AFIX 43 H00X 2 0.283754 0.361509 0.366351 11.00000 -1.20000 AFIX 0 C00Y 1 -0.173997 0.202205 0.589357 11.00000 0.02744 0.04978 = 0.05624 0.00479 0.00334 -0.00401 AFIX 43 H00Y 2 -0.260649 0.202195 0.567980 11.00000 -1.20000 AFIX 0 C00Z 1 0.249046 -0.002339 0.507737 11.00000 0.06323 0.03353 = 0.06368 -0.00394 0.01507 -0.00095 AFIX 43 H00Z 2 0.276473 -0.048357 0.527657 11.00000 -1.20000 AFIX 0 C010 1 0.107289 0.072365 0.420645 11.00000 0.04306 0.05561 = 0.05126 -0.01719 0.00719 -0.00312 C011 1 0.150206 0.551806 0.366052 11.00000 0.05420 0.03807 = 0.05628 0.00629 0.00755 -0.00021 AFIX 43 H011 2 0.116708 0.599682 0.366261 11.00000 -1.20000 AFIX 0 C012 1 0.309783 0.467035 0.332695 11.00000 0.04099 0.05870 = 0.05055 0.00914 0.01277 0.00028 AFIX 43 H012 2 0.384643 0.457712 0.310467 11.00000 -1.20000 AFIX 0 C013 1 0.285154 0.514261 0.606188 11.00000 0.05542 0.04156 = 0.05623 -0.00428 0.00121 0.00675 AFIX 43 H013 2 0.284128 0.554161 0.572536 11.00000 -1.20000 AFIX 0 C014 1 0.243760 0.464042 0.725733 11.00000 0.05137 0.06272 = 0.05314 -0.01962 0.01413 -0.00192 AFIX 43 H014 2 0.213259 0.469932 0.772814 11.00000 -1.20000 AFIX 0 C015 1 0.242271 0.523365 0.676228 11.00000 0.05156 0.04707 = 0.06317 -0.01673 0.00372 0.00684 AFIX 43 H015 2 0.212326 0.569425 0.690191 11.00000 -1.20000 AFIX 0 C016 1 0.144012 0.003821 0.451352 11.00000 0.05956 0.04345 = 0.06867 -0.01566 0.01466 -0.01120 AFIX 43 H016 2 0.097762 -0.038409 0.433967 11.00000 -1.20000 AFIX 0 C018 1 0.322239 0.600932 0.292029 11.00000 0.05107 0.06060 = 0.06179 0.01389 0.00204 -0.01984 AFIX 137 H01A 2 0.280133 0.605777 0.240367 11.00000 -1.50000 H01B 2 0.412539 0.590150 0.291342 11.00000 -1.50000 H01C 2 0.313638 0.646514 0.319230 11.00000 -1.50000 AFIX 0 C01A 1 0.486454 0.007750 0.632510 11.00000 0.07269 0.04192 = 0.06835 0.01276 0.00707 0.01829 AFIX 137 H01D 2 0.425314 -0.020532 0.657126 11.00000 -1.50000 H01E 2 0.552381 0.027180 0.670584 11.00000 -1.50000 H01F 2 0.525729 -0.023689 0.597905 11.00000 -1.50000 AFIX 0 O1 5 0.515011 0.280063 0.392839 11.00000 0.05722 0.05552 = 0.05109 0.00652 0.01959 0.00539 C2 1 0.578037 0.265288 0.323261 11.00000 0.04896 0.07268 = 0.04892 -0.00217 0.00601 -0.00045 AFIX 23 H2A 2 0.544958 0.219426 0.299260 11.00000 -1.20000 H2B 2 0.559307 0.305353 0.286632 11.00000 -1.20000 AFIX 0 C3 1 0.718691 0.259428 0.346043 11.00000 0.05422 0.06259 = 0.06469 -0.00438 0.00650 -0.00798 AFIX 137 H3A 2 0.761754 0.256065 0.301043 11.00000 -1.50000 H3B 2 0.737265 0.215818 0.376914 11.00000 -1.50000 H3C 2 0.748984 0.302570 0.375062 11.00000 -1.50000 AFIX 0 HKLF 4 REM exp_2650_a.res in P2(1)/c REM R1 = 0.0475 for 5608 Fo > 4sig(Fo) and 0.0559 for all 6586 data REM 418 parameters refined using 0 restraints END WGHT 0.0743 1.8512 REM Highest difference peak 1.438, deepest hole -0.431, 1-sigma level 0.057 Q1 1 0.6030 0.2789 0.4365 11.00000 0.05 1.44 Q2 1 0.6624 0.2604 0.3791 11.00000 0.05 0.56 Q3 1 -0.0019 0.1190 0.3178 11.00000 0.05 0.55 Q4 1 0.2571 0.2029 0.6277 11.00000 0.05 0.31 Q5 1 0.2704 0.2174 0.6370 11.00000 0.05 0.29 Q6 1 0.3988 0.2178 0.5187 11.00000 0.05 0.28 Q7 1 0.1050 0.3963 0.4152 11.00000 0.05 0.27 Q8 1 0.2609 0.2019 0.7467 11.00000 0.05 0.26 Q9 1 0.0600 0.2222 0.6240 11.00000 0.05 0.25 Q10 1 0.2605 0.1425 0.6855 11.00000 0.05 0.25 Q11 1 0.6020 0.2720 0.2815 11.00000 0.05 0.24 Q12 1 0.5431 0.2191 0.4736 11.00000 0.05 0.23 Q13 1 0.3043 0.2170 0.5686 11.00000 0.05 0.23 Q14 1 0.3529 0.3458 0.6227 11.00000 0.05 0.22 Q15 1 0.4643 0.2405 0.4776 11.00000 0.05 0.22 Q16 1 0.0305 0.3376 0.3767 11.00000 0.05 0.22 Q17 1 0.2969 0.0962 0.5000 11.00000 0.05 0.22 Q18 1 0.3121 0.1672 0.5215 11.00000 0.05 0.21 Q19 1 0.1345 0.0383 0.4218 11.00000 0.05 0.21 Q20 1 0.2474 0.2650 0.6853 11.00000 0.05 0.21 ; _shelx_res_checksum 2060 _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 1.139 _oxdiff_exptl_absorpt_empirical_full_min 0.906 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 S01 S 0.05425(5) 0.35124(3) 0.43777(3) 0.03523(14) Uani 1 1 d . . . . . S02 S 0.24885(5) 0.20016(3) 0.68608(3) 0.03665(15) Uani 1 1 d . . . . . Cl03 Cl -0.02463(8) 0.07795(5) 0.34918(5) 0.0714(2) Uani 1 1 d . . . . . O004 O 0.02081(17) 0.29701(10) 0.37870(9) 0.0470(4) Uani 1 1 d . . . . . O005 O -0.04785(16) 0.38282(10) 0.47436(10) 0.0470(4) Uani 1 1 d . . . . . O006 O 0.54451(15) 0.16334(10) 0.64740(10) 0.0460(4) Uani 1 1 d . . . . . N007 N 0.17040(16) 0.31526(10) 0.49887(10) 0.0323(4) Uani 1 1 d . . . . . O009 O 0.5203(2) 0.15815(10) 0.42345(13) 0.0640(6) Uani 1 1 d . . . . . N00A N 0.4196(2) 0.06887(10) 0.58991(12) 0.0425(4) Uani 1 1 d . . . . . C00B C 0.15870(18) 0.27009(11) 0.55389(11) 0.0293(4) Uani 1 1 d . . . . . C00C C 0.33373(19) 0.38532(12) 0.63500(12) 0.0352(4) Uani 1 1 d . . . . . C00D C 0.38782(19) 0.31056(12) 0.61451(12) 0.0338(4) Uani 1 1 d . . . . . H00D H 0.451489 0.295613 0.657829 0.041 Uiso 1 1 calc R . . . . C00E C 0.35923(19) 0.18990(12) 0.54805(12) 0.0330(4) Uani 1 1 d . . . . . C00F C 0.1389(2) 0.42420(12) 0.39993(12) 0.0357(4) Uani 1 1 d . . . . . C00G C 0.2739(2) 0.13187(12) 0.50408(13) 0.0352(4) Uani 1 1 d . . . . . C00H C 0.04788(19) 0.23627(12) 0.58349(12) 0.0317(4) Uani 1 1 d . . . . . C00I C 0.0825(2) 0.19969(12) 0.65344(12) 0.0331(4) Uani 1 1 d . . . . . C00J C 0.28853(19) 0.24509(11) 0.59896(11) 0.0309(4) Uani 1 1 d . . . . . C00K C 0.4553(2) 0.30747(12) 0.54378(13) 0.0366(5) Uani 1 1 d . . . . . H00K H 0.504731 0.346273 0.528131 0.044 Uiso 1 1 calc R . . . . C00L C 0.4370(2) 0.24412(12) 0.50628(13) 0.0361(5) Uani 1 1 d . . . . . C00M C 0.3118(2) 0.06209(13) 0.53347(14) 0.0402(5) Uani 1 1 d . . . . . C00N C -0.0829(2) 0.23608(13) 0.55094(14) 0.0390(5) Uani 1 1 d . . . . . H00N H -0.107609 0.258702 0.503768 0.047 Uiso 1 1 calc R . . . . C00O C 0.4551(2) 0.14045(12) 0.60172(13) 0.0376(5) Uani 1 1 d . . . . . C00P C 0.1719(2) 0.13762(13) 0.44577(14) 0.0411(5) Uani 1 1 d . . . . . H00P H 0.147019 0.183321 0.423991 0.049 Uiso 1 1 calc R . . . . C00Q C -0.0097(2) 0.16574(14) 0.69207(13) 0.0409(5) Uani 1 1 d . . . . . H00Q H 0.014211 0.141975 0.738714 0.049 Uiso 1 1 calc R . . . . C00R C 0.3300(2) 0.44558(13) 0.58564(14) 0.0425(5) Uani 1 1 d . . . . . H00R H 0.358065 0.439797 0.537870 0.051 Uiso 1 1 calc R . . . . C00S C 0.4958(2) 0.22164(14) 0.43745(16) 0.0466(6) Uani 1 1 d . . . . . C00T C 0.2602(2) 0.53877(14) 0.33146(13) 0.0440(5) Uani 1 1 d . . . . . C00U C 0.0889(2) 0.49491(14) 0.40042(15) 0.0451(5) Uani 1 1 d . . . . . H00U H 0.015020 0.504408 0.423521 0.054 Uiso 1 1 calc R . . . . C00V C -0.1383(2) 0.16808(15) 0.65954(14) 0.0451(5) Uani 1 1 d . . . . . H00V H -0.201566 0.146424 0.685173 0.054 Uiso 1 1 calc R . . . . C00W C 0.2907(2) 0.39524(15) 0.70572(14) 0.0452(5) Uani 1 1 d . . . . . H00W H 0.293153 0.355761 0.739973 0.054 Uiso 1 1 calc R . . . . C00X C 0.2502(2) 0.40938(14) 0.36625(14) 0.0447(5) Uani 1 1 d . . . . . H00X H 0.283754 0.361509 0.366351 0.054 Uiso 1 1 calc R . . . . C00Y C -0.1740(2) 0.20220(14) 0.58936(15) 0.0447(5) Uani 1 1 d . . . . . H00Y H -0.260649 0.202195 0.567980 0.054 Uiso 1 1 calc R . . . . C00Z C 0.2490(3) -0.00234(14) 0.50774(17) 0.0529(6) Uani 1 1 d . . . . . H00Z H 0.276473 -0.048357 0.527657 0.063 Uiso 1 1 calc R . . . . C010 C 0.1073(3) 0.07236(15) 0.42064(16) 0.0499(6) Uani 1 1 d . . . . . C011 C 0.1502(3) 0.55181(14) 0.36605(16) 0.0495(6) Uani 1 1 d . . . . . H011 H 0.116708 0.599682 0.366261 0.059 Uiso 1 1 calc R . . . . C012 C 0.3098(2) 0.46704(16) 0.33269(15) 0.0495(6) Uani 1 1 d . . . . . H012 H 0.384643 0.457712 0.310467 0.059 Uiso 1 1 calc R . . . . C013 C 0.2852(3) 0.51426(15) 0.60619(16) 0.0516(6) Uani 1 1 d . . . . . H013 H 0.284128 0.554161 0.572536 0.062 Uiso 1 1 calc R . . . . C014 C 0.2438(3) 0.46404(17) 0.72573(16) 0.0551(7) Uani 1 1 d . . . . . H014 H 0.213259 0.469932 0.772814 0.066 Uiso 1 1 calc R . . . . C015 C 0.2423(3) 0.52336(16) 0.67623(17) 0.0543(6) Uani 1 1 d . . . . . H015 H 0.212326 0.569425 0.690191 0.065 Uiso 1 1 calc R . . . . C016 C 0.1440(3) 0.00382(16) 0.45135(17) 0.0567(7) Uani 1 1 d . . . . . H016 H 0.097762 -0.038409 0.433967 0.068 Uiso 1 1 calc R . . . . C018 C 0.3222(3) 0.60093(17) 0.29203(17) 0.0583(7) Uani 1 1 d . . . . . H01A H 0.280133 0.605777 0.240367 0.087 Uiso 1 1 calc GR . . . . H01B H 0.412539 0.590150 0.291342 0.087 Uiso 1 1 calc GR . . . . H01C H 0.313638 0.646514 0.319230 0.087 Uiso 1 1 calc GR . . . . C01A C 0.4865(3) 0.00775(16) 0.63251(18) 0.0612(7) Uani 1 1 d . . . . . H01D H 0.425314 -0.020532 0.657126 0.092 Uiso 1 1 calc GR . . . . H01E H 0.552381 0.027180 0.670584 0.092 Uiso 1 1 calc GR . . . . H01F H 0.525729 -0.023689 0.597905 0.092 Uiso 1 1 calc GR . . . . O1 O 0.51501(18) 0.28006(11) 0.39284(11) 0.0535(5) Uani 1 1 d . . . . . C2 C 0.5780(3) 0.26529(19) 0.32326(16) 0.0569(7) Uani 1 1 d . . . . . H2A H 0.544958 0.219426 0.299260 0.068 Uiso 1 1 calc R . . . . H2B H 0.559307 0.305353 0.286632 0.068 Uiso 1 1 calc R . . . . C3 C 0.7187(3) 0.25943(18) 0.34604(18) 0.0606(7) Uani 1 1 d . . . . . H3A H 0.761754 0.256065 0.301043 0.091 Uiso 1 1 calc GR . . . . H3B H 0.737265 0.215818 0.376914 0.091 Uiso 1 1 calc GR . . . . H3C H 0.748984 0.302570 0.375062 0.091 Uiso 1 1 calc GR . . . . 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 S01 0.0316(3) 0.0382(3) 0.0352(3) 0.0075(2) 0.00199(19) 0.0016(2) S02 0.0304(3) 0.0470(3) 0.0319(3) 0.0081(2) 0.00162(19) -0.0017(2) Cl03 0.0562(4) 0.0827(5) 0.0702(5) -0.0274(4) -0.0105(3) -0.0025(4) O004 0.0527(10) 0.0486(10) 0.0367(8) 0.0039(7) -0.0053(7) -0.0088(8) O005 0.0368(8) 0.0476(9) 0.0587(10) 0.0163(8) 0.0139(7) 0.0091(7) O006 0.0308(8) 0.0478(9) 0.0575(10) 0.0060(8) -0.0012(7) 0.0046(7) N007 0.0313(8) 0.0342(9) 0.0313(8) 0.0029(7) 0.0037(7) 0.0030(7) O009 0.0766(14) 0.0385(10) 0.0863(14) -0.0107(9) 0.0467(12) -0.0026(9) N00A 0.0440(10) 0.0335(10) 0.0505(11) 0.0055(8) 0.0080(9) 0.0071(8) C00B 0.0274(9) 0.0307(10) 0.0298(9) -0.0034(8) 0.0039(7) 0.0019(8) C00C 0.0261(9) 0.0392(11) 0.0392(11) -0.0067(9) -0.0003(8) -0.0018(8) C00D 0.0273(9) 0.0354(11) 0.0380(11) 0.0009(8) 0.0016(8) -0.0002(8) C00E 0.0284(9) 0.0324(10) 0.0390(11) 0.0022(8) 0.0071(8) 0.0020(8) C00F 0.0359(10) 0.0383(11) 0.0326(10) 0.0061(9) 0.0028(8) 0.0006(9) C00G 0.0340(10) 0.0330(10) 0.0405(11) -0.0022(9) 0.0118(9) 0.0010(8) C00H 0.0284(9) 0.0345(10) 0.0324(10) -0.0005(8) 0.0048(8) -0.0001(8) C00I 0.0309(10) 0.0373(11) 0.0314(10) -0.0030(8) 0.0049(8) -0.0010(8) C00J 0.0275(9) 0.0338(10) 0.0314(10) 0.0038(8) 0.0034(7) 0.0003(8) C00K 0.0298(10) 0.0340(11) 0.0473(12) 0.0037(9) 0.0098(9) 0.0003(8) C00L 0.0323(10) 0.0340(11) 0.0440(12) 0.0045(9) 0.0125(9) 0.0020(8) C00M 0.0434(12) 0.0332(11) 0.0461(12) -0.0004(9) 0.0143(10) 0.0003(9) C00N 0.0306(10) 0.0426(12) 0.0425(12) 0.0058(9) -0.0003(9) -0.0003(9) C00O 0.0332(10) 0.0368(11) 0.0442(12) 0.0054(9) 0.0104(9) 0.0047(9) C00P 0.0408(12) 0.0410(12) 0.0423(12) -0.0069(10) 0.0085(9) 0.0029(9) C00Q 0.0386(11) 0.0505(13) 0.0346(11) 0.0032(10) 0.0084(9) -0.0063(10) C00R 0.0446(12) 0.0401(12) 0.0420(12) -0.0044(10) 0.0031(10) 0.0051(10) C00S 0.0474(13) 0.0388(12) 0.0574(15) -0.0016(11) 0.0216(11) -0.0004(10) C00T 0.0415(12) 0.0494(13) 0.0391(12) 0.0075(10) -0.0024(9) -0.0105(10) C00U 0.0443(12) 0.0410(12) 0.0516(13) 0.0061(10) 0.0127(10) 0.0025(10) C00V 0.0359(11) 0.0520(14) 0.0496(13) 0.0007(11) 0.0138(10) -0.0066(10) C00W 0.0450(13) 0.0483(13) 0.0433(12) -0.0065(10) 0.0095(10) -0.0039(10) C00X 0.0448(12) 0.0462(13) 0.0443(12) 0.0066(10) 0.0107(10) 0.0056(10) C00Y 0.0274(10) 0.0498(14) 0.0562(14) 0.0048(11) 0.0033(10) -0.0040(9) C00Z 0.0632(16) 0.0335(12) 0.0637(16) -0.0039(11) 0.0151(13) -0.0010(11) C010 0.0431(13) 0.0556(15) 0.0513(14) -0.0172(12) 0.0072(11) -0.0031(11) C011 0.0542(14) 0.0381(12) 0.0563(15) 0.0063(11) 0.0076(11) -0.0002(11) C012 0.0410(12) 0.0587(15) 0.0505(14) 0.0091(12) 0.0128(10) 0.0003(11) C013 0.0554(15) 0.0416(13) 0.0562(15) -0.0043(11) 0.0012(12) 0.0068(11) C014 0.0514(14) 0.0627(17) 0.0531(15) -0.0196(13) 0.0141(12) -0.0019(12) C015 0.0516(14) 0.0471(14) 0.0632(16) -0.0167(12) 0.0037(12) 0.0068(11) C016 0.0596(16) 0.0434(14) 0.0687(17) -0.0157(13) 0.0147(13) -0.0112(12) C018 0.0511(15) 0.0606(17) 0.0618(17) 0.0139(13) 0.0020(12) -0.0198(13) C01A 0.0727(19) 0.0419(14) 0.0683(18) 0.0128(13) 0.0071(15) 0.0183(13) O1 0.0572(11) 0.0555(11) 0.0511(10) 0.0065(8) 0.0196(8) 0.0054(9) C2 0.0490(14) 0.0727(19) 0.0489(15) -0.0022(13) 0.0060(11) -0.0005(13) C3 0.0542(16) 0.0626(18) 0.0647(18) -0.0044(14) 0.0065(13) -0.0080(13) 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' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 '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 O004 S01 N007 107.09(10) . . ? O004 S01 C00F 108.70(10) . . ? O005 S01 O004 118.19(11) . . ? O005 S01 N007 112.86(10) . . ? O005 S01 C00F 108.05(11) . . ? N007 S01 C00F 100.43(10) . . ? C00I S02 C00J 92.73(9) . . ? C00B N007 S01 127.65(15) . . ? C00M N00A C01A 125.6(2) . . ? C00O N00A C00M 111.67(19) . . ? C00O N00A C01A 122.7(2) . . ? N007 C00B C00H 133.73(18) . . ? N007 C00B C00J 114.29(17) . . ? C00H C00B C00J 111.98(17) . . ? C00R C00C C00D 121.7(2) . . ? C00W C00C C00D 119.9(2) . . ? C00W C00C C00R 118.3(2) . . ? C00C C00D C00J 116.89(17) . . ? C00K C00D C00C 117.03(18) . . ? C00K C00D C00J 101.21(17) . . ? C00G C00E C00J 115.96(16) . . ? C00G C00E C00O 101.58(17) . . ? C00L C00E C00G 120.68(19) . . ? C00L C00E C00J 100.69(16) . . ? C00L C00E C00O 108.77(17) . . ? C00O C00E C00J 108.88(17) . . ? C00U C00F S01 118.80(18) . . ? C00U C00F C00X 121.0(2) . . ? C00X C00F S01 120.09(18) . . ? C00M C00G C00E 108.23(19) . . ? C00P C00G C00E 132.0(2) . . ? C00P C00G C00M 119.7(2) . . ? C00I C00H C00B 112.66(18) . . ? C00I C00H C00N 118.79(19) . . ? C00N C00H C00B 128.55(19) . . ? C00H C00I S02 114.60(15) . . ? C00Q C00I S02 123.89(17) . . ? C00Q C00I C00H 121.5(2) . . ? C00B C00J S02 106.45(13) . . ? C00B C00J C00D 112.51(16) . . ? C00B C00J C00E 109.43(16) . . ? C00D C00J S02 113.70(14) . . ? C00D C00J C00E 103.18(16) . . ? C00E C00J S02 111.62(14) . . ? C00L C00K C00D 113.13(19) . . ? C00K C00L C00E 111.45(19) . . ? C00K C00L C00S 126.7(2) . . ? C00S C00L C00E 121.46(19) . . ? C00G C00M N00A 110.2(2) . . ? C00Z C00M N00A 127.3(2) . . ? C00Z C00M C00G 122.5(2) . . ? C00Y C00N C00H 119.5(2) . . ? O006 C00O N00A 126.5(2) . . ? O006 C00O C00E 125.3(2) . . ? N00A C00O C00E 108.18(19) . . ? C00G C00P C010 117.6(2) . . ? C00V C00Q C00I 118.4(2) . . ? C013 C00R C00C 121.2(2) . . ? O009 C00S C00L 123.2(2) . . ? O009 C00S O1 125.0(2) . . ? O1 C00S C00L 111.8(2) . . ? C011 C00T C012 118.5(2) . . ? C011 C00T C018 120.3(3) . . ? C012 C00T C018 121.2(2) . . ? C00F C00U C011 119.1(2) . . ? C00Q C00V C00Y 121.0(2) . . ? C00C C00W C014 120.3(3) . . ? C012 C00X C00F 118.8(2) . . ? C00N C00Y C00V 120.8(2) . . ? C00M C00Z C016 117.7(2) . . ? C00P C010 Cl03 118.8(2) . . ? C016 C010 Cl03 119.1(2) . . ? C016 C010 C00P 122.1(3) . . ? C00T C011 C00U 121.3(2) . . ? C00X C012 C00T 121.3(2) . . ? C015 C013 C00R 120.0(3) . . ? C015 C014 C00W 120.4(2) . . ? C013 C015 C014 119.7(2) . . ? C00Z C016 C010 120.4(2) . . ? C00S O1 C2 117.1(2) . . ? C3 C2 O1 108.5(2) . . ? 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 S01 O004 1.4352(18) . ? S01 O005 1.4282(17) . ? S01 N007 1.6421(17) . ? S01 C00F 1.759(2) . ? S02 C00I 1.750(2) . ? S02 C00J 1.826(2) . ? Cl03 C010 1.739(3) . ? O006 C00O 1.219(3) . ? N007 C00B 1.282(3) . ? O009 C00S 1.204(3) . ? N00A C00M 1.403(3) . ? N00A C00O 1.349(3) . ? N00A C01A 1.456(3) . ? C00B C00H 1.457(3) . ? C00B C00J 1.541(3) . ? C00C C00D 1.520(3) . ? C00C C00R 1.387(3) . ? C00C C00W 1.386(3) . ? C00D C00J 1.567(3) . ? C00D C00K 1.505(3) . ? C00E C00G 1.517(3) . ? C00E C00J 1.581(3) . ? C00E C00L 1.517(3) . ? C00E C00O 1.560(3) . ? C00F C00U 1.376(3) . ? C00F C00X 1.392(3) . ? C00G C00M 1.396(3) . ? C00G C00P 1.380(3) . ? C00H C00I 1.401(3) . ? C00H C00N 1.405(3) . ? C00I C00Q 1.386(3) . ? C00K C00L 1.319(3) . ? C00L C00S 1.481(3) . ? C00M C00Z 1.378(3) . ? C00N C00Y 1.375(3) . ? C00P C010 1.396(3) . ? C00Q C00V 1.384(3) . ? C00R C013 1.386(3) . ? C00S O1 1.343(3) . ? C00T C011 1.382(4) . ? C00T C012 1.390(4) . ? C00T C018 1.505(3) . ? C00U C011 1.386(3) . ? C00V C00Y 1.386(4) . ? C00W C014 1.393(4) . ? C00X C012 1.380(4) . ? C00Z C016 1.381(4) . ? C010 C016 1.381(4) . ? C013 C015 1.373(4) . ? C014 C015 1.377(4) . ? O1 C2 1.485(3) . ? C2 C3 1.469(4) . ?