#------------------------------------------------------------------------------ #$Date: 2016-04-05 18:05:21 +0300 (Tue, 05 Apr 2016) $ #$Revision: 181578 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/54/18/1541884.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_1541884 loop_ _publ_author_name 'Guo, Jing' 'Liu, Yangbin' 'Li, Xiangqiang' 'Liu, Xiaohua' 'Lin, Lili' 'Feng, Xiaoming' _publ_section_title ; Nickel(ii)-catalyzed enantioselective cyclopropanation of 3-alkenyl-oxindoles with phenyliodonium ylide via free carbene ; _journal_issue 4 _journal_name_full 'Chem. Sci.' _journal_page_first 2717 _journal_paper_doi 10.1039/C5SC03658E _journal_volume 7 _journal_year 2016 _chemical_absolute_configuration rmad _chemical_formula_moiety 'C24 H28 I N O9' _chemical_formula_sum 'C24 H28 I N O9' _chemical_formula_weight 601.37 _chemical_name_systematic ; ? ; _space_group_crystal_system tetragonal _space_group_IT_number 96 _space_group_name_Hall 'P 4nw 2abw' _space_group_name_H-M_alt 'P 43 21 2' _symmetry_space_group_name_Hall 'P 4nw 2abw' _symmetry_space_group_name_H-M 'P 43 21 2' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _audit_creation_date 2014-11-12 _audit_creation_method ; Olex2 1.2 (compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874) ; _audit_update_record ; 2014-12-09 deposited with the CCDC. 2016-01-04 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 10.52245(15) _cell_length_b 10.52245(15) _cell_length_c 48.9522(16) _cell_measurement_reflns_used 5792 _cell_measurement_temperature 293 _cell_measurement_theta_max 72.3450 _cell_measurement_theta_min 4.2870 _cell_volume 5420.1(2) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution ; Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008; Palatinus et al., 2012) ; _diffrn_ambient_temperature 293 _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 15.9595 _diffrn_detector_type EosS2 _diffrn_measured_fraction_theta_full 0.986 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_details ; 1 omega -31.00 53.00 1.0000 6.1500 omega____ theta____ kappa____ phi______ frames - 36.4171 -57.0000 -90.0000 84 2 omega 18.00 106.00 1.0000 6.1500 omega____ theta____ kappa____ phi______ frames - 36.4171 38.0000 0.0000 88 3 omega -31.00 53.00 1.0000 6.1500 omega____ theta____ kappa____ phi______ frames - 36.4171 -57.0000 90.0000 84 4 omega 18.00 106.00 1.0000 6.1500 omega____ theta____ kappa____ phi______ frames - 36.4171 38.0000 -60.0000 88 5 omega 40.00 94.00 1.0000 24.6100 omega____ theta____ kappa____ phi______ frames - 108.0000 -45.0000 -180.0000 54 6 omega 50.00 101.00 1.0000 24.6100 omega____ theta____ kappa____ phi______ frames - 108.0000 -94.0000 -90.0000 51 7 omega 97.00 176.00 1.0000 24.6100 omega____ theta____ kappa____ phi______ frames - 108.0000 45.0000 -90.0000 79 8 omega 49.00 75.00 1.0000 24.6100 omega____ theta____ kappa____ phi______ frames - 108.0000 -30.0000 30.0000 26 9 omega 38.00 72.00 1.0000 24.6100 omega____ theta____ kappa____ phi______ frames - 108.0000 -30.0000 90.0000 34 10 omega 44.00 88.00 1.0000 24.6100 omega____ theta____ kappa____ phi______ frames - 108.0000 -30.0000 -60.0000 44 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'New Gemini, Dual, Cu at zero, EosS2' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0019891000 _diffrn_orient_matrix_UB_12 0.0529647000 _diffrn_orient_matrix_UB_13 -0.0293549000 _diffrn_orient_matrix_UB_21 -0.0881634000 _diffrn_orient_matrix_UB_22 0.1085253000 _diffrn_orient_matrix_UB_23 0.0093295000 _diffrn_orient_matrix_UB_31 0.1168571000 _diffrn_orient_matrix_UB_32 0.0826891000 _diffrn_orient_matrix_UB_33 0.0065155000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0561 _diffrn_reflns_av_unetI/netI 0.0462 _diffrn_reflns_Laue_measured_fraction_full 0.986 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 58 _diffrn_reflns_limit_l_min -56 _diffrn_reflns_number 14454 _diffrn_reflns_point_group_measured_fraction_full 0.977 _diffrn_reflns_point_group_measured_fraction_max 0.991 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 67.018 _diffrn_reflns_theta_min 5.545 _diffrn_source 'Enhance (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 9.710 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.20879 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48) 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 1.474 _exptl_crystal_F_000 2432 _exptl_crystal_size_max 0.8 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.15 _refine_diff_density_max 1.042 _refine_diff_density_min -0.775 _refine_diff_density_rms 0.100 _refine_ls_abs_structure_details ; Flack x determined using 1500 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.007(5) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 324 _refine_ls_number_reflns 4801 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.037 _refine_ls_R_factor_all 0.0679 _refine_ls_R_factor_gt 0.0614 _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^)+(0.1121P)^2^+2.0027P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1629 _refine_ls_wR_factor_ref 0.1685 _reflns_Friedel_coverage 0.646 _reflns_Friedel_fraction_full 0.964 _reflns_Friedel_fraction_max 0.980 _reflns_number_gt 4332 _reflns_number_total 4801 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c5sc03658e2.cif _cod_data_source_block fxm-5i(bio) _cod_depositor_comments 'Adding full bibliography for 1541883--1541884.cif.' _cod_database_code 1541884 _shelxl_version_number 2014-1 _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. ; _reflns_odcompleteness_completeness 99.73 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C10(H10) 2.b Aromatic/amide H refined with riding coordinates: C29(H29), C74(H74), C6(H6) 2.c Idealised Me refined as rotating group: C1(H1A,H1B,H1C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B, H15C), C16(H16A,H16B,H16C), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C9(H9A,H9B,H9C) ; _shelx_res_file ; TITL CELL 1.54184 10.522454 10.522454 48.952185 90 90 90 ZERR 8 0.000151 0.000151 0.001566 0 0 0 LATT -1 SYMM 0.5-Y,0.5+X,0.75+Z SYMM -X,-Y,0.5+Z SYMM 0.5+Y,0.5-X,0.25+Z SYMM 0.5+X,0.5-Y,0.25-Z SYMM 0.5-X,0.5+Y,0.75-Z SYMM +Y,+X,-Z SYMM -Y,-X,0.5-Z SFAC C H I N O UNIT 192 224 8 8 72 L.S. 40 PLAN 20 TEMP 19.85 MORE -1 BOND $H CONF fmap 2 acta SHEL 999 0.837 REM G:/struct/olex2_fxm-5i(bio)/fxm-5i(bio).hkl WGHT 0.112100 2.002700 FVAR 2.97591 I7 3 -0.009105 -0.289892 -0.389608 11.00000 0.11719 0.06823 = 0.05821 -0.02058 0.00228 -0.02831 O1 5 -0.321362 -0.971210 -0.465824 11.00000 0.04770 0.04738 = 0.07001 -0.00525 -0.00820 -0.01061 C27 1 -0.226216 -0.788894 -0.444006 11.00000 0.03182 0.03584 = 0.04269 -0.00285 0.00056 -0.00646 O29 5 -0.366862 -0.587108 -0.415624 11.00000 0.06586 0.06345 = 0.03994 -0.00060 0.00695 0.00521 O40 5 -0.154339 -0.796655 -0.503155 11.00000 0.05179 0.04906 = 0.04654 -0.01097 0.01006 -0.01789 O44 5 -0.431029 -0.513481 -0.456428 11.00000 0.07201 0.06333 = 0.04266 -0.00787 -0.00482 0.03343 C12 1 -0.229457 -0.923239 -0.456264 11.00000 0.04360 0.03673 = 0.04420 0.00686 0.00053 -0.00216 O8 5 -0.123210 -0.753249 -0.400691 11.00000 0.07591 0.06871 = 0.05744 0.00948 -0.02021 -0.02815 C10 1 -0.311113 -0.692471 -0.456794 11.00000 0.03278 0.03823 = 0.03748 0.00120 -0.00086 -0.00142 AFIX 13 H10 2 -0.358755 -0.720945 -0.472870 11.00000 -1.20000 AFIX 0 O12 5 -0.301720 -0.865588 -0.403381 11.00000 0.08240 0.07776 = 0.04075 0.01267 -0.00524 -0.04093 N15 4 -0.021367 -0.626894 -0.494361 11.00000 0.03234 0.03466 = 0.04110 0.00014 0.00744 0.00097 C26 1 -0.164635 -0.682605 -0.460414 11.00000 0.03121 0.03776 = 0.03750 0.00314 -0.00145 0.00307 C29 1 0.075503 -0.439139 -0.469927 11.00000 0.04250 0.04267 = 0.05468 0.00036 0.00593 -0.00475 AFIX 43 H29 2 0.129505 -0.417972 -0.484262 11.00000 -1.20000 AFIX 0 C41 1 -0.007406 -0.399193 -0.425025 11.00000 0.05073 0.04010 = 0.04323 -0.01112 -0.00948 -0.00118 C64 1 -0.003647 -0.541727 -0.471808 11.00000 0.03308 0.03508 = 0.04060 0.00430 0.00124 0.00162 C74 1 0.073589 -0.368014 -0.446430 11.00000 0.04405 0.03732 = 0.06476 0.00296 -0.00367 -0.01006 AFIX 43 H74 2 0.127138 -0.298106 -0.444809 11.00000 -1.20000 AFIX 0 O81 5 -0.117526 -0.975248 -0.453628 11.00000 0.04919 0.04057 = 0.08171 0.00356 -0.01154 0.00233 C83 1 -0.086882 -0.575909 -0.450841 11.00000 0.03091 0.03462 = 0.04329 0.00196 -0.00252 0.00257 C101 1 -0.115924 -0.712932 -0.488856 11.00000 0.03458 0.03242 = 0.04261 0.00169 -0.00072 0.00002 C104 1 -0.372156 -0.592431 -0.440264 11.00000 0.02715 0.04035 = 0.04389 -0.00450 0.00596 -0.00250 O3 5 0.015425 -0.689594 -0.537410 11.00000 0.03743 0.05715 = 0.04479 -0.00730 0.00873 -0.00432 O4 5 0.171324 -0.588368 -0.514521 11.00000 0.03953 0.06190 = 0.06549 -0.00424 0.01210 -0.00956 C5 1 0.068594 -0.631119 -0.516406 11.00000 0.03466 0.04318 = 0.05028 0.00654 0.00773 0.00172 C6 1 -0.088182 -0.504316 -0.427042 11.00000 0.04495 0.03903 = 0.03779 0.00187 0.00210 -0.00756 AFIX 43 H6 2 -0.141853 -0.525866 -0.412677 11.00000 -1.20000 AFIX 0 C7 1 -0.209680 -0.795929 -0.413312 11.00000 0.04765 0.04122 = 0.04520 0.00619 -0.00912 -0.00876 C8 1 -0.496293 -0.398045 -0.446047 11.00000 0.08525 0.06874 = 0.07121 -0.01061 -0.00686 0.03210 C1 1 -0.394601 -0.311184 -0.432993 11.00000 0.10514 0.05000 = 0.13501 -0.01451 0.03278 0.00759 AFIX 137 H1A 2 -0.365420 -0.348452 -0.416228 11.00000 -1.50000 H1B 2 -0.430898 -0.229258 -0.429306 11.00000 -1.50000 H1C 2 -0.324321 -0.301889 -0.445337 11.00000 -1.50000 AFIX 0 C13 1 -0.310518 -0.874681 -0.374067 11.00000 0.16640 0.15799 = 0.04234 0.02237 -0.01033 -0.08355 AFIX 137 H13A 2 -0.390967 -0.911095 -0.369140 11.00000 -1.50000 H13B 2 -0.303306 -0.791405 -0.366209 11.00000 -1.50000 H13C 2 -0.243141 -0.927600 -0.367327 11.00000 -1.50000 AFIX 0 C14 1 -0.597931 -0.434514 -0.425142 11.00000 0.06902 0.11666 = 0.09578 -0.00662 0.01890 0.03413 AFIX 137 H14A 2 -0.659384 -0.489294 -0.433594 11.00000 -1.50000 H14B 2 -0.639404 -0.359138 -0.418615 11.00000 -1.50000 H14C 2 -0.558815 -0.478005 -0.410092 11.00000 -1.50000 AFIX 0 C15 1 -0.103856 -1.103866 -0.462470 11.00000 0.08168 0.05268 = 0.12400 0.00070 0.00309 0.01708 AFIX 137 H15A 2 -0.157610 -1.118569 -0.477997 11.00000 -1.50000 H15B 2 -0.127807 -1.160151 -0.447920 11.00000 -1.50000 H15C 2 -0.016963 -1.119333 -0.467436 11.00000 -1.50000 AFIX 0 C16 1 -0.559234 -0.347338 -0.471085 11.00000 0.18182 0.13032 = 0.08350 0.01344 -0.00818 0.10048 AFIX 137 H16A 2 -0.495672 -0.319823 -0.483850 11.00000 -1.50000 H16B 2 -0.612450 -0.276724 -0.466253 11.00000 -1.50000 H16C 2 -0.610083 -0.412836 -0.479264 11.00000 -1.50000 AFIX 0 C3 1 0.196990 -0.813567 -0.552985 11.00000 0.07091 0.05843 = 0.07606 -0.00670 0.00643 0.01888 AFIX 137 H3A 2 0.257874 -0.769988 -0.541780 11.00000 -1.50000 H3B 2 0.238707 -0.847169 -0.568860 11.00000 -1.50000 H3C 2 0.159613 -0.881881 -0.542767 11.00000 -1.50000 AFIX 0 C4 1 -0.000053 -0.790729 -0.579659 11.00000 0.09124 0.09510 = 0.05859 -0.01674 0.00881 -0.02201 AFIX 137 H4A 2 -0.026700 -0.867430 -0.570718 11.00000 -1.50000 H4B 2 0.039399 -0.811439 -0.596772 11.00000 -1.50000 H4C 2 -0.072598 -0.737465 -0.582874 11.00000 -1.50000 AFIX 0 C2 1 0.093861 -0.721326 -0.561759 11.00000 0.05235 0.04761 = 0.05022 -0.00736 0.01594 -0.00215 C9 1 0.140329 -0.602632 -0.575124 11.00000 0.11664 0.05188 = 0.06240 0.00048 0.03294 -0.01231 AFIX 137 H9A 2 0.072745 -0.541420 -0.575774 11.00000 -1.50000 H9B 2 0.168015 -0.621577 -0.593361 11.00000 -1.50000 H9C 2 0.210117 -0.568543 -0.564836 11.00000 -1.50000 AFIX 0 HKLF 4 REM REM R1 = 0.0614 for 4332 Fo > 4sig(Fo) and 0.0679 for all 4801 data REM 324 parameters refined using 0 restraints END WGHT 0.1121 2.0027 REM Highest difference peak 1.042, deepest hole -0.775, 1-sigma level 0.100 Q1 1 -0.0752 -0.2355 -0.3955 11.00000 0.05 1.04 Q2 1 -0.0623 -0.3561 -0.3884 11.00000 0.05 0.95 Q3 1 0.0619 -0.2327 -0.3898 11.00000 0.05 0.75 Q4 1 0.0546 -0.3446 -0.3951 11.00000 0.05 0.54 Q5 1 -0.4509 -0.2873 -0.4778 11.00000 0.05 0.50 Q6 1 -0.0087 -0.2948 -0.4092 11.00000 0.05 0.48 Q7 1 -0.0189 -0.3388 -0.4366 11.00000 0.05 0.35 Q8 1 -0.0545 -0.3467 -0.4327 11.00000 0.05 0.35 Q9 1 -0.0107 -0.2814 -0.3695 11.00000 0.05 0.32 Q10 1 -0.1377 -0.8232 -0.4045 11.00000 0.05 0.31 Q11 1 -0.3667 -0.4813 -0.4625 11.00000 0.05 0.30 Q12 1 -0.2085 -0.8054 -0.6099 11.00000 0.05 0.29 Q13 1 0.0589 -0.3542 -0.4306 11.00000 0.05 0.28 Q14 1 -0.5777 -0.3845 -0.4496 11.00000 0.05 0.28 Q15 1 -0.2256 -0.9176 -0.4056 11.00000 0.05 0.27 Q16 1 -0.5441 -0.1417 -0.4020 11.00000 0.05 0.27 Q17 1 -0.4335 -0.2668 -0.4024 11.00000 0.05 0.27 Q18 1 -0.0054 -0.4333 -0.4320 11.00000 0.05 0.26 Q19 1 -0.2625 -0.7263 -0.4564 11.00000 0.05 0.26 Q20 1 -0.1132 -0.8941 -0.6053 11.00000 0.05 0.26 ; _shelx_res_checksum 83396 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-y+1/2, x+1/2, z+3/4' '-x, -y, z+1/2' 'y+1/2, -x+1/2, z+1/4' 'x+1/2, -y+1/2, -z+1/4' '-x+1/2, y+1/2, -z+3/4' 'y, x, -z' '-y, -x, -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 I7 I -0.00911(8) -0.28989(7) -0.38961(2) 0.0812(3) Uani 1 1 d . O1 O -0.3214(5) -0.9712(5) -0.46582(12) 0.0550(13) Uani 1 1 d . C27 C -0.2262(6) -0.7889(7) -0.44401(13) 0.0368(14) Uani 1 1 d . O29 O -0.3669(6) -0.5871(6) -0.41562(10) 0.0564(14) Uani 1 1 d . O40 O -0.1543(5) -0.7967(5) -0.50316(10) 0.0491(13) Uani 1 1 d . O44 O -0.4310(6) -0.5135(6) -0.45643(10) 0.0593(15) Uani 1 1 d . C12 C -0.2295(7) -0.9232(7) -0.45626(14) 0.0415(15) Uani 1 1 d . O8 O -0.1232(7) -0.7532(6) -0.40069(12) 0.0674(18) Uani 1 1 d . C10 C -0.3111(6) -0.6925(7) -0.45679(13) 0.0362(14) Uani 1 1 d . H10 H -0.3588 -0.7209 -0.4729 0.043 Uiso 1 1 calc R O12 O -0.3017(7) -0.8656(7) -0.40338(11) 0.0670(18) Uani 1 1 d . N15 N -0.0214(5) -0.6269(5) -0.49436(11) 0.0360(11) Uani 1 1 d . C26 C -0.1646(6) -0.6826(7) -0.46041(13) 0.0355(14) Uani 1 1 d . C29 C 0.0755(8) -0.4391(7) -0.46993(16) 0.0466(17) Uani 1 1 d . H29 H 0.1295 -0.4180 -0.4843 0.056 Uiso 1 1 calc R C41 C -0.0074(8) -0.3992(7) -0.42503(14) 0.0447(15) Uani 1 1 d . C64 C -0.0036(7) -0.5417(6) -0.47181(13) 0.0363(13) Uani 1 1 d . C74 C 0.0736(8) -0.3680(7) -0.44643(16) 0.0487(17) Uani 1 1 d . H74 H 0.1271 -0.2981 -0.4448 0.058 Uiso 1 1 calc R O81 O -0.1175(5) -0.9752(5) -0.45363(13) 0.0572(14) Uani 1 1 d . C83 C -0.0869(6) -0.5759(6) -0.45084(13) 0.0363(14) Uani 1 1 d . C101 C -0.1159(6) -0.7129(7) -0.48886(13) 0.0365(13) Uani 1 1 d . C104 C -0.3722(6) -0.5924(7) -0.44026(13) 0.0371(14) Uani 1 1 d . O3 O 0.0154(5) -0.6896(5) -0.53741(10) 0.0465(11) Uani 1 1 d . O4 O 0.1713(5) -0.5884(6) -0.51452(12) 0.0556(14) Uani 1 1 d . C5 C 0.0686(7) -0.6311(7) -0.51641(14) 0.0427(15) Uani 1 1 d . C6 C -0.0882(7) -0.5043(7) -0.42704(13) 0.0406(14) Uani 1 1 d . H6 H -0.1419 -0.5259 -0.4127 0.049 Uiso 1 1 calc R C7 C -0.2097(8) -0.7959(7) -0.41331(14) 0.0447(16) Uani 1 1 d . C8 C -0.4963(12) -0.3980(10) -0.4460(2) 0.075(3) Uani 1 1 d . C1 C -0.3946(14) -0.3112(11) -0.4330(3) 0.097(4) Uani 1 1 d . H1A H -0.3654 -0.3485 -0.4162 0.145 Uiso 1 1 calc GR H1B H -0.4309 -0.2293 -0.4293 0.145 Uiso 1 1 calc GR H1C H -0.3243 -0.3019 -0.4453 0.145 Uiso 1 1 calc GR C13 C -0.3105(17) -0.8747(17) -0.37407(19) 0.122(6) Uani 1 1 d . H13A H -0.3910 -0.9111 -0.3691 0.183 Uiso 1 1 calc GR H13B H -0.3033 -0.7914 -0.3662 0.183 Uiso 1 1 calc GR H13C H -0.2431 -0.9276 -0.3673 0.183 Uiso 1 1 calc GR C14 C -0.5979(12) -0.4345(14) -0.4251(3) 0.094(4) Uani 1 1 d . H14A H -0.6594 -0.4893 -0.4336 0.141 Uiso 1 1 calc GR H14B H -0.6394 -0.3591 -0.4186 0.141 Uiso 1 1 calc GR H14C H -0.5588 -0.4780 -0.4101 0.141 Uiso 1 1 calc GR C15 C -0.1039(12) -1.1039(10) -0.4625(3) 0.086(3) Uani 1 1 d . H15A H -0.1576 -1.1186 -0.4780 0.129 Uiso 1 1 calc GR H15B H -0.1278 -1.1602 -0.4479 0.129 Uiso 1 1 calc GR H15C H -0.0170 -1.1193 -0.4674 0.129 Uiso 1 1 calc GR C16 C -0.5592(19) -0.3473(17) -0.4711(3) 0.132(7) Uani 1 1 d . H16A H -0.4957 -0.3198 -0.4838 0.198 Uiso 1 1 calc GR H16B H -0.6125 -0.2767 -0.4663 0.198 Uiso 1 1 calc GR H16C H -0.6101 -0.4128 -0.4793 0.198 Uiso 1 1 calc GR C3 C 0.1970(11) -0.8136(10) -0.5530(2) 0.068(2) Uani 1 1 d . H3A H 0.2579 -0.7700 -0.5418 0.103 Uiso 1 1 calc GR H3B H 0.2387 -0.8472 -0.5689 0.103 Uiso 1 1 calc GR H3C H 0.1596 -0.8819 -0.5428 0.103 Uiso 1 1 calc GR C4 C -0.0001(12) -0.7907(12) -0.5797(2) 0.082(3) Uani 1 1 d . H4A H -0.0267 -0.8674 -0.5707 0.122 Uiso 1 1 calc GR H4B H 0.0394 -0.8114 -0.5968 0.122 Uiso 1 1 calc GR H4C H -0.0726 -0.7375 -0.5829 0.122 Uiso 1 1 calc GR C2 C 0.0939(8) -0.7213(8) -0.56176(16) 0.0501(18) Uani 1 1 d . C9 C 0.1403(13) -0.6026(9) -0.5751(2) 0.077(3) Uani 1 1 d . H9A H 0.0727 -0.5414 -0.5758 0.115 Uiso 1 1 calc GR H9B H 0.1680 -0.6216 -0.5934 0.115 Uiso 1 1 calc GR H9C H 0.2101 -0.5685 -0.5648 0.115 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 I7 0.1172(7) 0.0682(4) 0.0582(4) -0.0206(3) 0.0023(3) -0.0283(4) O1 0.048(3) 0.047(3) 0.070(3) -0.005(3) -0.008(2) -0.011(2) C27 0.032(3) 0.036(3) 0.043(3) -0.003(3) 0.001(3) -0.006(3) O29 0.066(4) 0.063(3) 0.040(2) -0.001(2) 0.007(2) 0.005(3) O40 0.052(3) 0.049(3) 0.047(2) -0.011(2) 0.010(2) -0.018(2) O44 0.072(4) 0.063(4) 0.043(2) -0.008(3) -0.005(2) 0.033(3) C12 0.044(4) 0.037(4) 0.044(3) 0.007(3) 0.001(3) -0.002(3) O8 0.076(4) 0.069(4) 0.057(3) 0.009(3) -0.020(3) -0.028(3) C10 0.033(3) 0.038(4) 0.037(3) 0.001(3) -0.001(3) -0.001(3) O12 0.082(4) 0.078(4) 0.041(3) 0.013(3) -0.005(3) -0.041(4) N15 0.032(3) 0.035(3) 0.041(3) 0.000(2) 0.007(2) 0.001(2) C26 0.031(3) 0.038(4) 0.037(3) 0.003(3) -0.001(2) 0.003(3) C29 0.043(4) 0.043(4) 0.055(4) 0.000(3) 0.006(3) -0.005(3) C41 0.051(4) 0.040(3) 0.043(3) -0.011(3) -0.009(3) -0.001(3) C64 0.033(3) 0.035(3) 0.041(3) 0.004(2) 0.001(3) 0.002(3) C74 0.044(4) 0.037(4) 0.065(4) 0.003(3) -0.004(3) -0.010(3) O81 0.049(3) 0.041(3) 0.082(4) 0.004(3) -0.012(3) 0.002(2) C83 0.031(3) 0.035(3) 0.043(3) 0.002(3) -0.003(3) 0.003(3) C101 0.035(3) 0.032(3) 0.043(3) 0.002(3) -0.001(3) 0.000(3) C104 0.027(3) 0.040(4) 0.044(3) -0.005(3) 0.006(3) -0.003(3) O3 0.037(3) 0.057(3) 0.045(2) -0.007(2) 0.009(2) -0.004(2) O4 0.040(3) 0.062(4) 0.065(3) -0.004(3) 0.012(2) -0.010(3) C5 0.035(4) 0.043(4) 0.050(4) 0.007(3) 0.008(3) 0.002(3) C6 0.045(4) 0.039(4) 0.038(3) 0.002(3) 0.002(3) -0.008(3) C7 0.048(4) 0.041(4) 0.045(3) 0.006(3) -0.009(3) -0.009(3) C8 0.085(7) 0.069(6) 0.071(5) -0.011(4) -0.007(5) 0.032(6) C1 0.105(10) 0.050(6) 0.135(10) -0.015(6) 0.033(8) 0.008(6) C13 0.166(14) 0.158(14) 0.042(5) 0.022(6) -0.010(6) -0.084(12) C14 0.069(7) 0.117(10) 0.096(8) -0.007(7) 0.019(6) 0.034(7) C15 0.082(8) 0.053(6) 0.124(10) 0.001(6) 0.003(7) 0.017(5) C16 0.182(17) 0.130(13) 0.083(8) 0.013(8) -0.008(9) 0.100(13) C3 0.071(6) 0.058(6) 0.076(6) -0.007(4) 0.006(5) 0.019(5) C4 0.091(8) 0.095(8) 0.059(5) -0.017(5) 0.009(5) -0.022(7) C2 0.052(4) 0.048(4) 0.050(4) -0.007(3) 0.016(3) -0.002(4) C9 0.117(9) 0.052(5) 0.062(5) 0.000(4) 0.033(6) -0.012(6) 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' I I -0.3257 6.8362 '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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C10 C27 C12 116.7(6) C10 C27 C26 62.2(5) C10 C27 C7 121.3(6) C26 C27 C12 118.7(5) C7 C27 C12 110.2(6) C7 C27 C26 120.7(6) C104 O44 C8 122.2(6) O1 C12 C27 124.3(7) O1 C12 O81 126.6(7) O81 C12 C27 109.1(6) C27 C10 H10 115.8 C27 C10 C26 59.9(4) C26 C10 H10 115.8 C104 C10 C27 121.1(6) C104 C10 H10 115.8 C104 C10 C26 116.5(6) C7 O12 C13 117.0(8) C64 N15 C5 120.8(6) C101 N15 C64 110.8(5) C101 N15 C5 127.2(6) C27 C26 C10 57.9(4) C83 C26 C27 129.2(6) C83 C26 C10 124.6(6) C83 C26 C101 105.4(6) C101 C26 C27 118.3(6) C101 C26 C10 115.2(6) C64 C29 H29 120.7 C64 C29 C74 118.6(7) C74 C29 H29 120.7 C74 C41 I7 120.2(6) C74 C41 C6 120.4(6) C6 C41 I7 119.4(5) C29 C64 N15 128.7(6) C29 C64 C83 122.4(6) C83 C64 N15 108.9(6) C29 C74 C41 120.8(7) C29 C74 H74 119.6 C41 C74 H74 119.6 C12 O81 C15 117.3(8) C64 C83 C26 108.2(6) C6 C83 C26 132.7(6) C6 C83 C64 118.9(6) O40 C101 N15 128.1(6) O40 C101 C26 125.3(6) N15 C101 C26 106.6(6) O29 C104 O44 126.7(7) O29 C104 C10 124.1(7) O44 C104 C10 109.2(5) C5 O3 C2 119.5(6) O3 C5 N15 108.6(6) O4 C5 N15 122.4(7) O4 C5 O3 129.0(7) C41 C6 H6 120.6 C83 C6 C41 118.9(6) C83 C6 H6 120.6 O8 C7 C27 125.8(7) O8 C7 O12 125.8(7) O12 C7 C27 108.1(6) O44 C8 C1 107.8(9) O44 C8 C14 110.3(9) O44 C8 C16 102.5(9) C14 C8 C1 110.9(10) C16 C8 C1 115.8(13) C16 C8 C14 109.2(12) C8 C1 H1A 109.5 C8 C1 H1B 109.5 C8 C1 H1C 109.5 H1A C1 H1B 109.5 H1A C1 H1C 109.5 H1B C1 H1C 109.5 O12 C13 H13A 109.5 O12 C13 H13B 109.5 O12 C13 H13C 109.5 H13A C13 H13B 109.5 H13A C13 H13C 109.5 H13B C13 H13C 109.5 C8 C14 H14A 109.5 C8 C14 H14B 109.5 C8 C14 H14C 109.5 H14A C14 H14B 109.5 H14A C14 H14C 109.5 H14B C14 H14C 109.5 O81 C15 H15A 109.5 O81 C15 H15B 109.5 O81 C15 H15C 109.5 H15A C15 H15B 109.5 H15A C15 H15C 109.5 H15B C15 H15C 109.5 C8 C16 H16A 109.5 C8 C16 H16B 109.5 C8 C16 H16C 109.5 H16A C16 H16B 109.5 H16A C16 H16C 109.5 H16B C16 H16C 109.5 H3A C3 H3B 109.5 H3A C3 H3C 109.5 H3B C3 H3C 109.5 C2 C3 H3A 109.5 C2 C3 H3B 109.5 C2 C3 H3C 109.5 H4A C4 H4B 109.5 H4A C4 H4C 109.5 H4B C4 H4C 109.5 C2 C4 H4A 109.5 C2 C4 H4B 109.5 C2 C4 H4C 109.5 O3 C2 C3 108.3(7) O3 C2 C4 102.2(7) O3 C2 C9 110.2(7) C4 C2 C3 108.8(8) C9 C2 C3 115.1(9) C9 C2 C4 111.4(9) C2 C9 H9A 109.5 C2 C9 H9B 109.5 C2 C9 H9C 109.5 H9A C9 H9B 109.5 H9A C9 H9C 109.5 H9B C9 H9C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance I7 C41 2.081(6) O1 C12 1.187(9) C27 C12 1.536(10) C27 C10 1.490(10) C27 C26 1.522(9) C27 C7 1.514(9) O29 C104 1.209(9) O40 C101 1.196(9) O44 C104 1.304(9) O44 C8 1.485(11) C12 O81 1.305(10) O8 C7 1.188(10) C10 H10 0.9800 C10 C26 1.555(9) C10 C104 1.475(9) O12 C7 1.308(10) O12 C13 1.441(10) N15 C64 1.434(8) N15 C101 1.372(9) N15 C5 1.436(9) C26 C83 1.466(10) C26 C101 1.518(9) C29 H29 0.9300 C29 C64 1.367(10) C29 C74 1.372(11) C41 C74 1.390(12) C41 C6 1.398(10) C64 C83 1.396(9) C74 H74 0.9300 O81 C15 1.428(12) C83 C6 1.387(10) O3 C5 1.322(9) O3 C2 1.488(8) O4 C5 1.174(10) C6 H6 0.9300 C8 C1 1.546(18) C8 C14 1.529(17) C8 C16 1.492(16) C1 H1A 0.9600 C1 H1B 0.9600 C1 H1C 0.9600 C13 H13A 0.9600 C13 H13B 0.9600 C13 H13C 0.9600 C14 H14A 0.9600 C14 H14B 0.9600 C14 H14C 0.9600 C15 H15A 0.9600 C15 H15B 0.9600 C15 H15C 0.9600 C16 H16A 0.9600 C16 H16B 0.9600 C16 H16C 0.9600 C3 H3A 0.9600 C3 H3B 0.9600 C3 H3C 0.9600 C3 C2 1.518(13) C4 H4A 0.9600 C4 H4B 0.9600 C4 H4C 0.9600 C4 C2 1.509(13) C2 C9 1.492(12) C9 H9A 0.9600 C9 H9B 0.9600 C9 H9C 0.9600 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 I7 C41 C74 C29 -179.9(6) I7 C41 C6 C83 179.5(5) O1 C12 O81 C15 -1.6(12) C27 C12 O81 C15 176.5(8) C27 C10 C26 C83 -118.2(7) C27 C10 C26 C101 108.8(6) C27 C10 C104 O29 -6.2(11) C27 C10 C104 O44 173.9(6) C27 C26 C83 C64 151.5(7) C27 C26 C83 C6 -33.1(12) C27 C26 C101 O40 25.3(10) C27 C26 C101 N15 -154.5(6) C12 C27 C10 C26 -110.0(7) C12 C27 C10 C104 145.4(6) C12 C27 C26 C10 106.9(7) C12 C27 C26 C83 -142.4(7) C12 C27 C26 C101 3.4(9) C12 C27 C7 O8 118.8(9) C12 C27 C7 O12 -56.4(8) C10 C27 C12 O1 -33.2(10) C10 C27 C12 O81 148.7(6) C10 C27 C26 C83 110.7(8) C10 C27 C26 C101 -103.5(6) C10 C27 C7 O8 -99.7(10) C10 C27 C7 O12 85.2(9) C10 C26 C83 C64 -134.2(6) C10 C26 C83 C6 41.2(11) C10 C26 C101 O40 -40.3(10) C10 C26 C101 N15 139.9(6) N15 C64 C83 C26 -2.5(7) N15 C64 C83 C6 -178.6(6) C26 C27 C12 O1 -104.5(8) C26 C27 C12 O81 77.4(7) C26 C27 C10 C104 -104.7(7) C26 C27 C7 O8 -25.6(12) C26 C27 C7 O12 159.3(7) C26 C10 C104 O29 -75.5(9) C26 C10 C104 O44 104.6(7) C26 C83 C6 C41 -174.1(7) C29 C64 C83 C26 175.2(7) C29 C64 C83 C6 -0.9(11) C64 N15 C101 O40 -179.9(7) C64 N15 C101 C26 -0.1(7) C64 N15 C5 O3 -163.6(6) C64 N15 C5 O4 16.9(11) C64 C29 C74 C41 -0.3(12) C64 C83 C6 C41 0.9(10) C74 C29 C64 N15 177.8(7) C74 C29 C64 C83 0.6(12) C74 C41 C6 C83 -0.6(11) C83 C26 C101 O40 178.4(7) C83 C26 C101 N15 -1.4(7) C101 N15 C64 C29 -175.9(7) C101 N15 C64 C83 1.6(8) C101 N15 C5 O3 29.8(10) C101 N15 C5 O4 -149.7(8) C101 C26 C83 C64 2.3(7) C101 C26 C83 C6 177.8(7) C104 O44 C8 C1 63.0(12) C104 O44 C8 C14 -58.1(12) C104 O44 C8 C16 -174.3(12) C104 C10 C26 C27 112.2(6) C104 C10 C26 C83 -6.0(9) C104 C10 C26 C101 -138.9(6) C5 N15 C64 C29 15.4(11) C5 N15 C64 C83 -167.1(6) C5 N15 C101 O40 -12.1(12) C5 N15 C101 C26 167.7(6) C5 O3 C2 C3 62.7(9) C5 O3 C2 C4 177.4(8) C5 O3 C2 C9 -64.1(10) C6 C41 C74 C29 0.3(12) C7 C27 C12 O1 110.3(8) C7 C27 C12 O81 -67.8(7) C7 C27 C10 C26 110.8(7) C7 C27 C10 C104 6.1(10) C7 C27 C26 C10 -111.7(7) C7 C27 C26 C83 -1.0(11) C7 C27 C26 C101 144.9(7) C8 O44 C104 O29 3.4(13) C8 O44 C104 C10 -176.7(8) C13 O12 C7 C27 -174.4(11) C13 O12 C7 O8 10.5(17) C2 O3 C5 N15 -172.3(6) C2 O3 C5 O4 7.2(12)