#------------------------------------------------------------------------------ #$Date: 2020-05-01 01:19:13 +0300 (Fri, 01 May 2020) $ #$Revision: 251336 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/79/1557972.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_1557972 loop_ _publ_author_name 'Singh, Bara' 'Bankar, Siddheshwar K.' 'Kumar, Ketan' 'Ramasastry, S. S. V.' _publ_section_title ; Palladium-catalysed 5-endo-trig allylic (hetero)arylation ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D0SC01932A _journal_year 2020 _chemical_absolute_configuration S _chemical_formula_moiety 'C26 H19 N O S' _chemical_formula_sum 'C26 H19 N O S' _chemical_formula_weight 393.48 _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2019-11-11 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-11-13 deposited with the CCDC. 2020-04-20 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 114.722(18) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 9.8666(13) _cell_length_b 9.9949(9) _cell_length_c 11.3565(17) _cell_measurement_reflns_used 2284 _cell_measurement_temperature 298.0(2) _cell_measurement_theta_max 31.9130 _cell_measurement_theta_min 3.0430 _cell_volume 1017.3(3) _computing_cell_refinement 'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)' _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_temperature 298.0(2) _diffrn_detector 'CCD plate' _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.950 _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 -69.00 119.00 0.50 25.00 -- 29.89 54.00-180.00 376 2 \w -69.00 119.00 0.50 25.00 -- 29.89 54.00 -60.00 376 3 \w -69.00 23.00 0.50 25.00 -- 29.89 54.00 60.00 184 ; _diffrn_measurement_device 'two-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Mini (ROW)' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0610215000 _diffrn_orient_matrix_UB_12 -0.0155063000 _diffrn_orient_matrix_UB_13 0.0152118000 _diffrn_orient_matrix_UB_21 -0.0379952000 _diffrn_orient_matrix_UB_22 -0.0297055000 _diffrn_orient_matrix_UB_23 -0.0619661000 _diffrn_orient_matrix_UB_31 0.0331403000 _diffrn_orient_matrix_UB_32 -0.0625346000 _diffrn_orient_matrix_UB_33 0.0256377000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0429 _diffrn_reflns_av_unetI/netI 0.0855 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.950 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 12440 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.882 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 33.064 _diffrn_reflns_theta_min 2.838 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.176 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.98321 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.7f (Rigaku Oxford Diffraction, 2015) 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 1.285 _exptl_crystal_description plate _exptl_crystal_F_000 412 _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.09 _refine_diff_density_max 0.220 _refine_diff_density_min -0.312 _refine_diff_density_rms 0.044 _refine_ls_abs_structure_details ; Flack x determined using 970 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.00(5) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 263 _refine_ls_number_reflns 6810 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.026 _refine_ls_R_factor_all 0.1435 _refine_ls_R_factor_gt 0.0593 _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^)+(0.0389P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1060 _refine_ls_wR_factor_ref 0.1470 _reflns_Friedel_coverage 0.771 _reflns_Friedel_fraction_full 0.999 _reflns_Friedel_fraction_max 0.807 _reflns_number_gt 3217 _reflns_number_total 6810 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; sam_03_81_rt.res created by SHELXL-2014/7 TITL sam_03_81_rt_a.res in P2(1) REM Old TITL SAM_03_81_RT in P2(1) REM SHELXT solution in P2(1) REM R1 0.146, Rweak 0.037, Alpha 0.009, Orientation as input REM Flack x = 0.091 ( 0.067 ) from Parsons' quotients REM Formula found by SHELXT: C26 N O S CELL 0.71073 9.8666 9.9949 11.3565 90 114.722 90 ZERR 2 0.0013 0.0009 0.0017 0 0.018 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H N O S UNIT 52 38 2 2 2 L.S. 4 0 0 PLAN 20 list 4 BOND $H CONF HTAB fmap 2 53 acta OMIT 5 -13 3 REM REM REM WGHT 0.038900 FVAR 0.99838 S001 5 -0.048685 0.074292 0.293201 11.00000 0.06416 0.07611 = 0.07254 -0.00311 0.02824 -0.02316 O002 4 0.088505 0.551738 0.205789 11.00000 0.06181 0.06656 = 0.06455 0.00449 0.02866 0.01195 N003 3 0.345119 0.542475 0.299697 11.00000 0.05382 0.04684 = 0.05582 0.00013 0.02345 -0.00216 C004 1 0.204690 0.487407 0.246152 11.00000 0.05554 0.04862 = 0.04473 0.00037 0.02545 0.00417 C005 1 0.388837 0.317274 0.303052 11.00000 0.04684 0.04977 = 0.04156 0.00119 0.01845 -0.00219 C006 1 0.220234 0.334469 0.242916 11.00000 0.04533 0.04927 = 0.04252 -0.00024 0.01849 -0.00249 C007 1 0.151151 0.248773 0.439478 11.00000 0.04587 0.04894 = 0.04995 0.00474 0.02371 0.00568 C008 1 0.141505 0.258936 0.310831 11.00000 0.04747 0.04729 = 0.04726 -0.00591 0.02259 -0.00696 C009 1 0.143107 0.281616 0.105249 11.00000 0.05646 0.05941 = 0.04393 -0.00147 0.02247 -0.00149 C00A 1 0.456335 0.442932 0.334557 11.00000 0.05086 0.04526 = 0.05273 0.00229 0.02241 -0.00104 C00B 1 0.050922 0.149411 0.443383 11.00000 0.04700 0.05603 = 0.06323 0.00649 0.02719 0.00195 C00C 1 0.240732 0.316895 0.553498 11.00000 0.05857 0.04809 = 0.05141 -0.00565 0.02327 0.00216 AFIX 43 H00C 2 0.307230 0.382627 0.553053 11.00000 -1.20000 AFIX 0 C00D 1 0.356390 0.742746 0.176397 11.00000 0.05276 0.04985 = 0.06187 -0.00010 0.01884 -0.00537 C00E 1 0.041025 0.174987 0.224084 11.00000 0.05294 0.06272 = 0.04991 -0.00600 0.01915 -0.01526 C00F 1 0.474716 0.203990 0.325849 11.00000 0.06300 0.05034 = 0.06588 0.00180 0.03115 0.00160 AFIX 43 H00F 2 0.430593 0.120067 0.303638 11.00000 -1.20000 AFIX 0 C00G 1 0.629775 0.217486 0.383115 11.00000 0.05917 0.05802 = 0.08060 0.00837 0.03494 0.01183 AFIX 43 H00G 2 0.689705 0.141701 0.400348 11.00000 -1.20000 AFIX 0 C00H 1 0.369249 0.686327 0.303640 11.00000 0.07477 0.04170 = 0.06146 -0.00063 0.02924 -0.00383 AFIX 23 H00A 2 0.467786 0.706251 0.370118 11.00000 -1.20000 H00B 2 0.296795 0.730166 0.327686 11.00000 -1.20000 AFIX 0 C00I 1 0.040790 0.189320 0.096904 11.00000 0.06275 0.06658 = 0.04576 -0.01105 0.01605 -0.00548 AFIX 43 H00I 2 -0.019722 0.142673 0.022569 11.00000 -1.20000 AFIX 0 C00J 1 0.040795 0.117699 0.559026 11.00000 0.06196 0.07056 = 0.06422 0.01280 0.03422 0.00458 AFIX 43 H00J 2 -0.024759 0.051901 0.561214 11.00000 -1.20000 AFIX 0 C00K 1 0.694581 0.341778 0.414228 11.00000 0.05150 0.07299 = 0.08295 0.01212 0.02462 0.00235 AFIX 43 H00K 2 0.798053 0.348805 0.451684 11.00000 -1.20000 AFIX 0 C00L 1 0.227819 0.283870 0.667258 11.00000 0.08016 0.06351 = 0.04821 -0.00465 0.02786 0.01288 AFIX 43 H00L 2 0.286218 0.328508 0.743602 11.00000 -1.20000 AFIX 0 C00M 1 0.609361 0.456319 0.391059 11.00000 0.04875 0.05771 = 0.07982 0.00396 0.01979 -0.00715 AFIX 43 H00M 2 0.653856 0.540129 0.412923 11.00000 -1.20000 AFIX 0 C00N 1 0.410076 0.677069 0.097935 11.00000 0.07744 0.06805 = 0.07167 0.00063 0.03191 0.00135 AFIX 43 H00N 2 0.455483 0.594046 0.123553 11.00000 -1.20000 AFIX 0 C00O 1 0.129185 0.185310 0.669040 11.00000 0.08496 0.07549 = 0.06716 0.01306 0.04957 0.01642 AFIX 43 H00O 2 0.123277 0.165018 0.746678 11.00000 -1.20000 AFIX 0 C00P 1 0.179218 0.333092 -0.002008 11.00000 0.09234 0.08066 = 0.05049 0.00191 0.03549 0.00636 AFIX 137 H00D 2 0.178413 0.429133 -0.001477 11.00000 -1.50000 H00E 2 0.106138 0.301190 -0.083619 11.00000 -1.50000 H00H 2 0.276275 0.301982 0.010249 11.00000 -1.50000 AFIX 0 C00Q 1 0.289274 0.866422 0.136067 11.00000 0.09648 0.05408 = 0.08217 0.00910 0.03650 0.00466 AFIX 43 H00Q 2 0.251852 0.912542 0.187173 11.00000 -1.20000 AFIX 0 C00R 1 0.398056 0.731671 -0.018067 11.00000 0.09730 0.10442 = 0.07216 -0.00035 0.04295 -0.01712 AFIX 43 H00R 2 0.434213 0.685629 -0.070122 11.00000 -1.20000 AFIX 0 C00S 1 0.332357 0.854106 -0.055024 11.00000 0.13176 0.09960 = 0.08028 0.02495 0.04454 -0.02017 AFIX 43 H00S 2 0.324890 0.891788 -0.132380 11.00000 -1.20000 AFIX 0 C00T 1 0.277394 0.922068 0.020148 11.00000 0.13690 0.07820 = 0.10523 0.03298 0.04716 0.00897 AFIX 43 H00T 2 0.232316 1.005098 -0.006265 11.00000 -1.20000 AFIX 0 HKLF 4 REM sam_03_81_rt_a.res in P2(1) REM R1 = 0.0593 for 3217 Fo > 4sig(Fo) and 0.1435 for all 6810 data REM 263 parameters refined using 1 restraints END WGHT 0.0389 0.0000 REM Instructions for potential hydrogen bonds EQIV $1 -x, y-1/2, -z HTAB C00I O002_$1 REM Highest difference peak 0.220, deepest hole -0.312, 1-sigma level 0.044 Q1 1 0.0784 -0.0057 0.2363 11.00000 0.05 0.17 Q2 1 0.3427 0.4478 0.4570 11.00000 0.05 0.16 Q3 1 0.6231 0.5531 0.1605 11.00000 0.05 0.16 Q4 1 0.8658 0.4230 0.5595 11.00000 0.05 0.15 Q5 1 0.0545 -0.0977 0.2679 11.00000 0.05 0.15 Q6 1 0.8877 0.2209 0.4942 11.00000 0.05 0.15 Q7 1 -0.2022 0.0861 0.2275 11.00000 0.05 0.14 Q8 1 0.1017 0.8571 -0.1743 11.00000 0.05 0.14 Q9 1 0.7740 0.5534 0.6007 11.00000 0.05 0.14 Q10 1 0.1736 0.8927 -0.2011 11.00000 0.05 0.14 Q11 1 0.6033 0.6135 0.2246 11.00000 0.05 0.14 Q12 1 0.2065 0.1003 0.2386 11.00000 0.05 0.13 Q13 1 0.0759 0.9174 0.1848 11.00000 0.05 0.13 Q14 1 -0.0056 -0.1115 0.6002 11.00000 0.05 0.13 Q15 1 0.0547 0.0062 0.1378 11.00000 0.05 0.13 Q16 1 0.2069 0.9094 0.2780 11.00000 0.05 0.13 Q17 1 0.2596 0.8187 -0.2819 11.00000 0.05 0.13 Q18 1 -0.1599 0.1164 0.0946 11.00000 0.05 0.13 Q19 1 0.1846 0.6660 0.2129 11.00000 0.05 0.13 Q20 1 0.6252 0.6817 0.3954 11.00000 0.05 0.13 REM The information below was added by Olex2. REM REM R1 = 0.0593 for 3217 Fo > 4sig(Fo) and 0.1435 for all 12458 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.22, deepest hole -0.31 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.1435 REM R1_gt = 0.0593 REM wR_ref = 0.1470 REM GOOF = 1.026 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 12458 REM Reflections_gt = 3217 REM Parameters = n/a REM Hole = -0.31 REM Peak = 0.22 REM Flack = 0.01(6) ; _cod_data_source_file d0sc01932a2.cif _cod_data_source_block sam_03_81_rt _cod_database_code 1557972 _shelx_shelxl_version_number 2014/7 _chemical_oxdiff_formula 'C26 H14 N1 O1 S1' _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. ; _reflns_odcompleteness_completeness 99.80 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 25.30 _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 Secondary CH2 refined with riding coordinates: C20(H20a,H20b) 2.b Aromatic/amide H refined with riding coordinates: C5(H5), C16(H16), C17(H17), C9(H9), C2(H2), C18(H18), C4(H4), C19(H19), C26(H26), C3(H3), C22(H22), C25(H25), C24(H24), C23(H23) 2.c Idealised Me refined as rotating group: C15(H15a,H15b,H15c) ; _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 1.032 _oxdiff_exptl_absorpt_empirical_full_min 0.969 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -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 S001 S -0.04868(13) 0.07429(11) 0.29320(13) 0.0711(4) Uani 1 1 d . . . . . O002 O 0.0885(3) 0.5517(3) 0.2058(3) 0.0635(8) Uani 1 1 d . . . . . N003 N 0.3451(3) 0.5425(3) 0.2997(3) 0.0520(8) Uani 1 1 d . . . . . C004 C 0.2047(4) 0.4874(4) 0.2462(4) 0.0481(9) Uani 1 1 d . . . . . C005 C 0.3888(4) 0.3173(4) 0.3031(4) 0.0461(8) Uani 1 1 d . . . . . C006 C 0.2202(4) 0.3345(4) 0.2429(4) 0.0457(8) Uani 1 1 d . . . . . C007 C 0.1512(4) 0.2488(4) 0.4395(4) 0.0470(9) Uani 1 1 d . . . . . C008 C 0.1415(4) 0.2589(3) 0.3108(4) 0.0464(8) Uani 1 1 d . . . . . C009 C 0.1431(4) 0.2816(4) 0.1052(4) 0.0528(9) Uani 1 1 d . . . . . C00A C 0.4563(4) 0.4429(3) 0.3346(4) 0.0494(9) Uani 1 1 d . . . . . C00B C 0.0509(4) 0.1494(4) 0.4434(4) 0.0540(10) Uani 1 1 d . . . . . C00C C 0.2407(5) 0.3169(4) 0.5535(4) 0.0526(9) Uani 1 1 d . . . . . H00C H 0.3072 0.3826 0.5531 0.063 Uiso 1 1 calc R . . . . C00D C 0.3564(4) 0.7427(4) 0.1764(4) 0.0566(10) Uani 1 1 d . . . . . C00E C 0.0410(4) 0.1750(4) 0.2241(4) 0.0560(10) Uani 1 1 d . . . . . C00F C 0.4747(5) 0.2040(4) 0.3258(4) 0.0583(10) Uani 1 1 d . . . . . H00F H 0.4306 0.1201 0.3036 0.070 Uiso 1 1 calc R . . . . C00G C 0.6298(5) 0.2175(4) 0.3831(5) 0.0640(11) Uani 1 1 d . . . . . H00G H 0.6897 0.1417 0.4003 0.077 Uiso 1 1 calc R . . . . C00H C 0.3692(5) 0.6863(4) 0.3036(4) 0.0591(11) Uani 1 1 d . . . . . H00A H 0.4678 0.7063 0.3701 0.071 Uiso 1 1 calc R . . . . H00B H 0.2968 0.7302 0.3277 0.071 Uiso 1 1 calc R . . . . C00I C 0.0408(5) 0.1893(4) 0.0969(4) 0.0606(11) Uani 1 1 d . . . . . H00I H -0.0197 0.1427 0.0226 0.073 Uiso 1 1 calc R . . . . C00J C 0.0408(5) 0.1177(4) 0.5590(5) 0.0629(12) Uani 1 1 d . . . . . H00J H -0.0248 0.0519 0.5612 0.076 Uiso 1 1 calc R . . . . C00K C 0.6946(5) 0.3418(5) 0.4142(5) 0.0703(13) Uani 1 1 d . . . . . H00K H 0.7981 0.3488 0.4517 0.084 Uiso 1 1 calc R . . . . C00L C 0.2278(5) 0.2839(4) 0.6673(4) 0.0636(11) Uani 1 1 d . . . . . H00L H 0.2862 0.3285 0.7436 0.076 Uiso 1 1 calc R . . . . C00M C 0.6094(5) 0.4563(4) 0.3911(5) 0.0645(12) Uani 1 1 d . . . . . H00M H 0.6539 0.5401 0.4129 0.077 Uiso 1 1 calc R . . . . C00N C 0.4101(5) 0.6771(5) 0.0979(5) 0.0721(13) Uani 1 1 d . . . . . H00N H 0.4555 0.5940 0.1236 0.087 Uiso 1 1 calc R . . . . C00O C 0.1292(5) 0.1853(5) 0.6690(5) 0.0699(13) Uani 1 1 d . . . . . H00O H 0.1233 0.1650 0.7467 0.084 Uiso 1 1 calc R . . . . C00P C 0.1792(5) 0.3331(5) -0.0020(4) 0.0726(13) Uani 1 1 d . . . . . H00D H 0.1784 0.4291 -0.0015 0.109 Uiso 1 1 calc GR . . . . H00E H 0.1061 0.3012 -0.0836 0.109 Uiso 1 1 calc GR . . . . H00H H 0.2763 0.3020 0.0102 0.109 Uiso 1 1 calc GR . . . . C00Q C 0.2893(6) 0.8664(4) 0.1361(5) 0.0779(14) Uani 1 1 d . . . . . H00Q H 0.2519 0.9125 0.1872 0.093 Uiso 1 1 calc R . . . . C00R C 0.3981(6) 0.7317(6) -0.0181(5) 0.0888(16) Uani 1 1 d . . . . . H00R H 0.4342 0.6856 -0.0701 0.107 Uiso 1 1 calc R . . . . C00S C 0.3324(7) 0.8541(7) -0.0550(6) 0.104(2) Uani 1 1 d . . . . . H00S H 0.3249 0.8918 -0.1324 0.125 Uiso 1 1 calc R . . . . C00T C 0.2774(8) 0.9221(6) 0.0201(7) 0.108(2) Uani 1 1 d . . . . . H00T H 0.2323 1.0051 -0.0063 0.130 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 S001 0.0642(6) 0.0761(8) 0.0725(8) -0.0031(6) 0.0282(6) -0.0232(6) O002 0.0618(16) 0.0666(18) 0.065(2) 0.0045(15) 0.0287(15) 0.0119(16) N003 0.0538(18) 0.0468(17) 0.056(2) 0.0001(14) 0.0235(16) -0.0022(15) C004 0.056(2) 0.049(2) 0.045(2) 0.0004(16) 0.0255(19) 0.0042(18) C005 0.047(2) 0.0498(19) 0.042(2) 0.0012(16) 0.0184(17) -0.0022(16) C006 0.0453(19) 0.0493(19) 0.043(2) -0.0002(16) 0.0185(17) -0.0025(16) C007 0.0459(19) 0.0489(19) 0.050(2) 0.0047(17) 0.0237(19) 0.0057(17) C008 0.0475(19) 0.0473(19) 0.047(2) -0.0059(16) 0.0226(18) -0.0070(16) C009 0.056(2) 0.059(2) 0.044(2) -0.0015(17) 0.022(2) -0.0015(19) C00A 0.051(2) 0.0453(19) 0.053(3) 0.0023(17) 0.0224(19) -0.0010(17) C00B 0.047(2) 0.056(2) 0.063(3) 0.0065(18) 0.027(2) 0.0019(18) C00C 0.059(2) 0.048(2) 0.051(3) -0.0056(18) 0.023(2) 0.0022(18) C00D 0.053(2) 0.050(2) 0.062(3) -0.0001(19) 0.019(2) -0.0054(18) C00E 0.053(2) 0.063(2) 0.050(3) -0.0060(19) 0.019(2) -0.0153(19) C00F 0.063(2) 0.050(2) 0.066(3) 0.0018(19) 0.031(2) 0.0016(19) C00G 0.059(2) 0.058(2) 0.081(3) 0.008(2) 0.035(2) 0.012(2) C00H 0.075(3) 0.0417(19) 0.061(3) -0.0006(18) 0.029(2) -0.0038(19) C00I 0.063(2) 0.067(2) 0.046(3) -0.011(2) 0.016(2) -0.005(2) C00J 0.062(3) 0.071(3) 0.064(3) 0.013(2) 0.034(3) 0.005(2) C00K 0.051(2) 0.073(3) 0.083(4) 0.012(2) 0.025(2) 0.002(2) C00L 0.080(3) 0.064(2) 0.048(3) -0.0047(19) 0.028(2) 0.013(2) C00M 0.049(2) 0.058(2) 0.080(4) 0.004(2) 0.020(2) -0.0072(19) C00N 0.077(3) 0.068(3) 0.072(4) 0.001(2) 0.032(3) 0.001(3) C00O 0.085(3) 0.075(3) 0.067(3) 0.013(3) 0.050(3) 0.016(3) C00P 0.092(3) 0.081(3) 0.050(3) 0.002(2) 0.035(3) 0.006(3) C00Q 0.096(4) 0.054(3) 0.082(4) 0.009(2) 0.037(3) 0.005(3) C00R 0.097(4) 0.104(4) 0.072(4) 0.000(3) 0.043(3) -0.017(3) C00S 0.132(6) 0.100(5) 0.080(4) 0.025(4) 0.045(4) -0.020(4) C00T 0.137(6) 0.078(4) 0.105(5) 0.033(4) 0.047(5) 0.009(4) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C00E S001 C00B 90.4(2) . . ? C004 N003 C00A 111.3(3) . . ? C004 N003 C00H 122.1(3) . . ? C00A N003 C00H 126.2(3) . . ? O002 C004 N003 124.6(3) . . ? O002 C004 C006 126.9(4) . . ? N003 C004 C006 108.5(3) . . ? C00A C005 C006 109.2(3) . . ? C00F C005 C006 130.6(3) . . ? C00F C005 C00A 120.2(3) . . ? C005 C006 C004 101.7(3) . . ? C008 C006 C004 114.1(3) . . ? C008 C006 C005 114.5(3) . . ? C008 C006 C009 102.1(3) . . ? C009 C006 C004 111.0(3) . . ? C009 C006 C005 114.0(3) . . ? C00B C007 C008 109.5(3) . . ? C00C C007 C008 131.1(3) . . ? C00C C007 C00B 119.4(4) . . ? C007 C008 C006 137.0(3) . . ? C00E C008 C006 108.4(3) . . ? C00E C008 C007 114.5(3) . . ? C00I C009 C006 110.5(3) . . ? C00I C009 C00P 127.4(4) . . ? C00P C009 C006 122.1(4) . . ? C005 C00A N003 109.3(3) . . ? C00M C00A N003 129.4(3) . . ? C00M C00A C005 121.3(4) . . ? C007 C00B S001 112.8(3) . . ? C00J C00B S001 126.2(3) . . ? C00J C00B C007 121.0(4) . . ? C007 C00C H00C 120.8 . . ? C00L C00C C007 118.4(4) . . ? C00L C00C H00C 120.8 . . ? C00N C00D C00H 122.7(4) . . ? C00N C00D C00Q 118.1(5) . . ? C00Q C00D C00H 119.2(4) . . ? C008 C00E S001 112.8(3) . . ? C008 C00E C00I 111.0(4) . . ? C00I C00E S001 136.1(3) . . ? C005 C00F H00F 120.7 . . ? C005 C00F C00G 118.6(4) . . ? C00G C00F H00F 120.7 . . ? C00F C00G H00G 119.7 . . ? C00K C00G C00F 120.6(4) . . ? C00K C00G H00G 119.7 . . ? N003 C00H C00D 113.2(3) . . ? N003 C00H H00A 108.9 . . ? N003 C00H H00B 108.9 . . ? C00D C00H H00A 108.9 . . ? C00D C00H H00B 108.9 . . ? H00A C00H H00B 107.8 . . ? C009 C00I C00E 108.1(4) . . ? C009 C00I H00I 126.0 . . ? C00E C00I H00I 126.0 . . ? C00B C00J H00J 120.7 . . ? C00O C00J C00B 118.6(4) . . ? C00O C00J H00J 120.7 . . ? C00G C00K H00K 119.3 . . ? C00G C00K C00M 121.4(4) . . ? C00M C00K H00K 119.3 . . ? C00C C00L H00L 119.4 . . ? C00C C00L C00O 121.2(4) . . ? C00O C00L H00L 119.4 . . ? C00A C00M C00K 118.0(4) . . ? C00A C00M H00M 121.0 . . ? C00K C00M H00M 121.0 . . ? C00D C00N H00N 119.2 . . ? C00D C00N C00R 121.6(5) . . ? C00R C00N H00N 119.2 . . ? C00J C00O C00L 121.3(4) . . ? C00J C00O H00O 119.3 . . ? C00L C00O H00O 119.3 . . ? C009 C00P H00D 109.5 . . ? C009 C00P H00E 109.5 . . ? C009 C00P H00H 109.5 . . ? H00D C00P H00E 109.5 . . ? H00D C00P H00H 109.5 . . ? H00E C00P H00H 109.5 . . ? C00D C00Q H00Q 119.7 . . ? C00D C00Q C00T 120.6(6) . . ? C00T C00Q H00Q 119.7 . . ? C00N C00R H00R 120.5 . . ? C00S C00R C00N 119.1(6) . . ? C00S C00R H00R 120.5 . . ? C00R C00S H00S 119.5 . . ? C00R C00S C00T 120.9(6) . . ? C00T C00S H00S 119.5 . . ? C00Q C00T H00T 120.2 . . ? C00S C00T C00Q 119.6(6) . . ? C00S C00T H00T 120.2 . . ? 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 S001 C00B 1.743(5) . ? S001 C00E 1.730(4) . ? O002 C004 1.224(4) . ? N003 C004 1.374(5) . ? N003 C00A 1.410(5) . ? N003 C00H 1.455(5) . ? C004 C006 1.538(5) . ? C005 C006 1.521(5) . ? C005 C00A 1.396(5) . ? C005 C00F 1.372(5) . ? C006 C008 1.506(5) . ? C006 C009 1.519(5) . ? C007 C008 1.427(5) . ? C007 C00B 1.415(5) . ? C007 C00C 1.401(5) . ? C008 C00E 1.357(5) . ? C009 C00I 1.341(6) . ? C009 C00P 1.496(5) . ? C00A C00M 1.378(5) . ? C00B C00J 1.395(6) . ? C00C H00C 0.9300 . ? C00C C00L 1.390(5) . ? C00D C00H 1.506(6) . ? C00D C00N 1.378(6) . ? C00D C00Q 1.387(6) . ? C00E C00I 1.450(6) . ? C00F H00F 0.9300 . ? C00F C00G 1.396(6) . ? C00G H00G 0.9300 . ? C00G C00K 1.374(6) . ? C00H H00A 0.9700 . ? C00H H00B 0.9700 . ? C00I H00I 0.9300 . ? C00J H00J 0.9300 . ? C00J C00O 1.366(6) . ? C00K H00K 0.9300 . ? C00K C00M 1.379(6) . ? C00L H00L 0.9300 . ? C00L C00O 1.391(6) . ? C00M H00M 0.9300 . ? C00N H00N 0.9300 . ? C00N C00R 1.384(7) . ? C00O H00O 0.9300 . ? C00P H00D 0.9600 . ? C00P H00E 0.9600 . ? C00P H00H 0.9600 . ? C00Q H00Q 0.9300 . ? C00Q C00T 1.388(8) . ? C00R H00R 0.9300 . ? C00R C00S 1.366(8) . ? C00S H00S 0.9300 . ? C00S C00T 1.368(8) . ? C00T H00T 0.9300 . ? 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 S001 C00B C00J C00O 178.9(3) . . . . ? S001 C00E C00I C009 -176.2(4) . . . . ? O002 C004 C006 C005 178.7(4) . . . . ? O002 C004 C006 C008 -57.5(5) . . . . ? O002 C004 C006 C009 57.1(5) . . . . ? N003 C004 C006 C005 0.3(4) . . . . ? N003 C004 C006 C008 124.1(3) . . . . ? N003 C004 C006 C009 -121.3(3) . . . . ? N003 C00A C00M C00K -179.3(4) . . . . ? C004 N003 C00A C005 0.3(4) . . . . ? C004 N003 C00A C00M -179.6(4) . . . . ? C004 N003 C00H C00D -79.0(5) . . . . ? C004 C006 C008 C007 -62.5(6) . . . . ? C004 C006 C008 C00E 121.6(4) . . . . ? C004 C006 C009 C00I -123.3(4) . . . . ? C004 C006 C009 C00P 55.1(5) . . . . ? C005 C006 C008 C007 54.1(6) . . . . ? C005 C006 C008 C00E -121.8(4) . . . . ? C005 C006 C009 C00I 122.6(4) . . . . ? C005 C006 C009 C00P -59.0(5) . . . . ? C005 C00A C00M C00K 0.8(7) . . . . ? C005 C00F C00G C00K -0.9(7) . . . . ? C006 C005 C00A N003 -0.1(4) . . . . ? C006 C005 C00A C00M 179.8(4) . . . . ? C006 C005 C00F C00G 179.9(4) . . . . ? C006 C008 C00E S001 176.1(2) . . . . ? C006 C008 C00E C00I -1.6(5) . . . . ? C006 C009 C00I C00E 0.5(5) . . . . ? C007 C008 C00E S001 -0.9(5) . . . . ? C007 C008 C00E C00I -178.6(3) . . . . ? C007 C00B C00J C00O 0.4(6) . . . . ? C007 C00C C00L C00O 0.3(6) . . . . ? C008 C006 C009 C00I -1.4(4) . . . . ? C008 C006 C009 C00P 177.0(4) . . . . ? C008 C007 C00B S001 0.0(4) . . . . ? C008 C007 C00B C00J 178.7(4) . . . . ? C008 C007 C00C C00L -178.8(4) . . . . ? C008 C00E C00I C009 0.7(5) . . . . ? C009 C006 C008 C007 177.7(4) . . . . ? C009 C006 C008 C00E 1.8(4) . . . . ? C00A N003 C004 O002 -178.8(4) . . . . ? C00A N003 C004 C006 -0.3(4) . . . . ? C00A N003 C00H C00D 93.5(5) . . . . ? C00A C005 C006 C004 -0.1(4) . . . . ? C00A C005 C006 C008 -123.6(3) . . . . ? C00A C005 C006 C009 119.4(4) . . . . ? C00A C005 C00F C00G 1.2(6) . . . . ? C00B S001 C00E C008 0.7(3) . . . . ? C00B S001 C00E C00I 177.7(5) . . . . ? C00B C007 C008 C006 -175.2(4) . . . . ? C00B C007 C008 C00E 0.6(4) . . . . ? C00B C007 C00C C00L 0.1(5) . . . . ? C00B C00J C00O C00L -0.1(6) . . . . ? C00C C007 C008 C006 3.8(7) . . . . ? C00C C007 C008 C00E 179.6(4) . . . . ? C00C C007 C00B S001 -179.1(3) . . . . ? C00C C007 C00B C00J -0.5(5) . . . . ? C00C C00L C00O C00J -0.3(6) . . . . ? C00D C00N C00R C00S 0.5(8) . . . . ? C00D C00Q C00T C00S 0.1(9) . . . . ? C00E S001 C00B C007 -0.4(3) . . . . ? C00E S001 C00B C00J -179.0(4) . . . . ? C00F C005 C006 C004 -178.9(4) . . . . ? C00F C005 C006 C008 57.6(6) . . . . ? C00F C005 C006 C009 -59.4(6) . . . . ? C00F C005 C00A N003 178.9(4) . . . . ? C00F C005 C00A C00M -1.2(6) . . . . ? C00F C00G C00K C00M 0.5(8) . . . . ? C00G C00K C00M C00A -0.5(7) . . . . ? C00H N003 C004 O002 -5.3(6) . . . . ? C00H N003 C004 C006 173.1(3) . . . . ? C00H N003 C00A C005 -172.9(4) . . . . ? C00H N003 C00A C00M 7.2(7) . . . . ? C00H C00D C00N C00R -179.4(4) . . . . ? C00H C00D C00Q C00T 179.1(5) . . . . ? C00N C00D C00H N003 -39.0(6) . . . . ? C00N C00D C00Q C00T -0.2(7) . . . . ? C00N C00R C00S C00T -0.7(9) . . . . ? C00P C009 C00I C00E -177.8(4) . . . . ? C00Q C00D C00H N003 141.7(4) . . . . ? C00Q C00D C00N C00R 0.0(7) . . . . ? C00R C00S C00T C00Q 0.4(10) . . . . ?