#------------------------------------------------------------------------------ #$Date: 2020-05-01 01:01:38 +0300 (Fri, 01 May 2020) $ #$Revision: 251333 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/64/7126465.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_7126465 loop_ _publ_author_name 'Tang, Pan-Ting' 'Wang, Liang-Neng' 'Shao, Youxiang' 'Wei, Yi' 'Li, Ming' 'Zhang, Ni-Juan' 'Luo, Xiao-Peng' 'Ke, Zhuofeng' 'Liu, Yue-Jin' 'Zeng, Ming-Hua' _publ_section_title ; Synthesis of seven-membered lactones by regioselective and stereoselective iodolactonization of electron-deficient olefins ; _journal_name_full 'Chemical Communications' _journal_paper_doi 10.1039/C9CC10080F _journal_year 2020 _chemical_formula_moiety 'C17 H13 I O4' _chemical_formula_sum 'C17 H13 I O4' _chemical_formula_weight 408.17 _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 2019-05-26 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-05-26 deposited with the CCDC. 2020-04-30 downloaded from the CCDC. ; _cell_angle_alpha 74.922(2) _cell_angle_beta 85.722(2) _cell_angle_gamma 61.931(3) _cell_formula_units_Z 2 _cell_length_a 9.5534(3) _cell_length_b 9.6302(3) _cell_length_c 10.2451(2) _cell_measurement_reflns_used 9496 _cell_measurement_temperature 100 _cell_measurement_theta_max 76.4640 _cell_measurement_theta_min 4.4100 _cell_volume 801.80(5) _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_temperature 100 _diffrn_detector 'CCD plate' _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.965 _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 -24.00 59.00 0.50 0.17 -- 43.80 -55.00 43.00 166 2 \w 92.00 120.00 0.50 0.69 -- 111.75 -55.00 43.00 56 3 \w 75.00 139.00 0.50 0.69 -- 111.75 -77.00 60.00 128 4 \w 64.00 177.00 0.50 0.69 -- 111.75 15.00 30.00 226 5 \w 94.00 176.00 0.50 0.69 -- 111.75 45.00 -90.00 164 6 \w 95.00 177.00 0.50 0.69 -- 111.75 77.00-150.00 164 7 \w 91.00 176.00 0.50 0.69 -- 111.75 55.00-173.00 170 8 \w 61.00 88.00 0.50 0.17 -- 43.80 55.00-173.00 54 9 \w 24.00 50.00 0.50 0.17 -- 43.80 55.00-173.00 52 10 \w 17.00 58.00 0.50 0.17 -- 43.80 77.00 -90.00 82 11 \w 17.00 61.00 0.50 0.17 -- 43.80 78.00-164.72 88 12 \w 0.00 29.00 0.50 0.17 -- -43.80 55.00-173.00 58 13 \w -34.00 -2.00 0.50 0.17 -- -43.80 55.00-173.00 64 14 \w -78.00 -21.00 0.50 0.17 -- -43.80 -57.00 -30.00 114 15 \w -43.00 -18.00 0.50 0.17 -- -43.80 -77.00 -30.00 50 16 \w -52.00 -15.00 0.50 0.17 -- -43.80 -77.00 60.00 74 17 \w -61.00 -27.00 0.50 0.17 -- -43.80 -37.00 60.00 68 18 \w -68.00 -24.00 0.50 0.17 -- -43.80 -55.00 43.00 88 19 \w -66.00 -19.00 0.50 0.17 -- -43.80 -77.00 -60.00 94 20 \w -87.00 -61.00 0.50 0.69 -- -90.25 -77.00-150.00 52 21 \w -87.00 -60.00 0.50 0.69 -- -90.25 -82.00-151.41 54 22 \w -92.00 -61.00 0.50 0.69 -- -90.25 -77.00-110.46 62 23 \w -87.00 -61.00 0.50 0.69 -- -90.25 -77.00 -60.00 52 24 \w -91.00 -64.00 0.50 0.69 -- -90.25 -77.00 0.00 54 25 \w -90.00 -61.00 0.50 0.69 -- -90.25 -77.00 30.00 58 26 \w -87.00 -62.00 0.50 0.69 -- -90.25 -74.00 84.53 50 27 \w -91.00 -60.00 0.50 0.69 -- -90.25 -79.00 111.17 62 28 \w -104.00 -63.00 0.50 0.69 -- -90.25 -75.00 74.77 82 29 \w -92.00 -59.00 0.50 0.69 -- -90.25 -81.00 63.03 66 30 \w -98.00 -62.00 0.50 0.69 -- -90.25 -74.00 -15.60 72 31 \w -106.00 -68.00 0.50 0.69 -- -90.25 -57.00 20.43 76 32 \w -98.00 -62.00 0.50 0.69 -- -90.25 -77.00 -30.00 72 33 \w -94.00 -62.00 0.50 0.69 -- -90.25 -74.00 -76.74 64 34 \w -101.00 -59.00 0.50 0.69 -- -90.25 -81.00-125.94 84 35 \w -114.00 -16.00 0.50 0.17 -- -43.80 -19.00-180.00 196 36 \w -88.00 -63.00 0.50 0.69 -- -90.25 55.00-173.00 50 37 \w -118.00 -15.00 0.50 0.17 -- -43.80 -77.00-180.00 206 38 \w 31.00 97.00 0.50 0.17 -- 43.80-125.00 -90.00 132 39 \w 39.00 82.00 0.50 0.69 -- 111.75 -55.00 43.00 86 40 \w 39.00 106.00 0.50 0.69 -- 111.75 -94.00 30.00 134 41 \w 39.00 117.00 0.50 0.69 -- 111.75-125.00 -60.00 156 42 \w 41.00 121.00 0.50 0.69 -- 111.75-125.00-120.00 160 43 \w 44.00 103.00 0.50 0.69 -- 111.75 -94.00 -30.00 118 44 \w 89.00 177.00 0.50 0.69 -- 111.75 61.00 120.00 176 45 \w 147.00 174.00 0.50 0.69 -- 111.75 125.00 120.00 54 46 \w 107.00 143.00 0.50 0.69 -- 111.75 125.00 120.00 72 47 \w 86.00 176.00 0.50 0.69 -- 111.75 77.00 60.00 180 48 \w -95.00 -59.00 0.50 0.69 -- -90.25 -82.00 177.82 72 49 \w -101.00 -59.00 0.50 0.69 -- -90.25 -81.00 133.69 84 50 \w -114.00 -77.00 0.50 0.17 -- -43.80 -55.00 43.00 74 51 \w -111.00 -61.00 0.50 0.69 -- -90.25 -77.00-180.00 100 52 \w -109.00 -62.00 0.50 0.69 -- -90.25 -77.00 -90.00 94 53 \w -131.00 -68.00 0.50 0.69 -- -90.25 -61.00 -60.00 126 54 \w -122.00 -95.00 0.50 0.69 -- -90.25 -77.00-150.00 54 55 \w -158.00-132.00 0.50 0.69 -- -90.25 -77.00-110.46 52 56 \w -159.00-134.00 0.50 0.69 -- -90.25 -77.00 -90.00 50 57 \w -158.00-131.00 0.50 0.69 -- -90.25 -77.00 -30.00 54 58 \w -134.00 -64.00 0.50 0.69 -- -90.25 -70.00 0.67 140 59 \w -121.00 -64.00 0.50 0.17 -- -43.80 -37.00 60.00 114 60 \w -124.00 -61.00 0.50 0.69 -- -90.25 -77.00 150.00 126 61 \w -140.00-113.00 0.50 0.69 -- -90.25 -74.00 84.53 54 62 \w -140.00-113.00 0.50 0.69 -- -90.25 -77.00 30.00 54 63 \w -163.00-113.00 0.50 0.69 -- -90.25 -55.00 43.00 100 64 \w -151.00-123.00 0.50 0.69 -- -90.25 -81.00 133.69 56 65 \w -162.00-130.00 0.50 0.69 -- -90.25 -75.00 74.77 64 66 \w -164.00-108.00 0.50 0.69 -- -90.25 -79.00 111.17 112 67 \w -160.00-133.00 0.50 0.69 -- -90.25 -81.00-125.94 54 68 \w -163.00-104.00 0.50 0.69 -- -90.25-125.00-180.00 118 69 \w -109.00 -16.00 0.50 0.69 -- -90.25 77.00 150.00 186 ; _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 0.1726221000 _diffrn_orient_matrix_UB_12 -0.0663760000 _diffrn_orient_matrix_UB_13 -0.0434945000 _diffrn_orient_matrix_UB_21 0.0402530000 _diffrn_orient_matrix_UB_22 -0.1688262000 _diffrn_orient_matrix_UB_23 0.0942076000 _diffrn_orient_matrix_UB_31 -0.0456662000 _diffrn_orient_matrix_UB_32 -0.0475432000 _diffrn_orient_matrix_UB_33 -0.1164583000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0586 _diffrn_reflns_av_unetI/netI 0.0345 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.965 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 16140 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.965 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 76.634 _diffrn_reflns_theta_min 4.477 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 15.828 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.68369 _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 1.691 _exptl_crystal_description block _exptl_crystal_F_000 400 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _refine_diff_density_max 1.049 _refine_diff_density_min -1.272 _refine_diff_density_rms 0.095 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 200 _refine_ls_number_reflns 3261 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.081 _refine_ls_R_factor_all 0.0413 _refine_ls_R_factor_gt 0.0378 _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^)+(0.0607P)^2^+0.8048P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1012 _refine_ls_wR_factor_ref 0.1074 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3043 _reflns_number_total 3261 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9cc10080f2.cif _cod_data_source_block hubu-lyj-tpt-jacs-20190512 _cod_original_cell_volume 801.80(4) _cod_database_code 7126465 _shelx_shelxl_version_number 2014/7 _chemical_oxdiff_formula 'I C O N H' _chemical_oxdiff_usercomment colorless _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 0.144 _shelx_estimated_absorpt_t_min 0.144 _reflns_odcompleteness_completeness 100.00 _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: C14(H14), C15(H15) 2.b Aromatic/amide H refined with riding coordinates: C11(H11), C10(H10), C8(H8), C4(H4), C9(H9), C1(H1), C3(H3), C2(H2) 2.c Idealised Me refined as rotating group: C17(H17A,H17B,H17C) ; _shelx_res_file ; hubu-lyj-tpt-jacs-20190512.res created by SHELXL-2014/7 TITL hubu-lyj-tpt-jacs-20190512_a.res in P-1 REM Old TITL HUBU-LYJ-TPT-jacs-20190512 in P1 REM SHELXT solution in P-1: R1 0.191, Rweak 0.021, Alpha 0.074 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C17 O4 I CELL 1.54184 9.5534 9.6302 10.2451 74.922 85.722 61.931 ZERR 2 0.0003 0.0003 0.0002 0.002 0.002 0.003 LATT 1 SFAC C H I O UNIT 34 26 2 8 L.S. 4 0 0 PLAN 20 SIZE 0.2 0.2 0.2 TEMP -173.15 BOND list 4 fmap 2 53 acta OMIT 8 6 9 OMIT -11 -4 3 OMIT 8 5 8 REM REM REM WGHT 0.060700 0.804800 FVAR 0.64877 I1 3 0.706974 0.465623 0.887384 11.00000 0.05307 0.07878 = 0.05300 -0.02830 0.00532 -0.03956 O2 4 0.517256 0.328432 0.603064 11.00000 0.04384 0.04040 = 0.03903 -0.01532 0.00799 -0.02388 O4 4 0.889648 0.363301 0.589700 11.00000 0.04045 0.06132 = 0.05500 -0.01236 0.00967 -0.02483 O1 4 0.445119 0.193584 0.505662 11.00000 0.09142 0.06220 = 0.04282 -0.02724 0.01406 -0.04941 O3 4 0.855651 0.153168 0.712493 11.00000 0.04987 0.03939 = 0.09336 -0.01289 0.01424 -0.01353 C14 1 0.526893 0.374294 0.725578 11.00000 0.03508 0.03382 = 0.03532 -0.01095 0.00269 -0.01693 AFIX 13 H14 2 0.561238 0.276666 0.804571 11.00000 -1.20000 AFIX 0 C12 1 0.361380 0.501013 0.745028 11.00000 0.03763 0.03495 = 0.03372 -0.01326 0.00240 -0.01576 C15 1 0.655538 0.427290 0.702134 11.00000 0.03905 0.03854 = 0.03447 -0.01140 0.00212 -0.02053 AFIX 13 H15 2 0.619427 0.529767 0.627865 11.00000 -1.20000 AFIX 0 C7 1 0.250737 0.444570 0.789907 11.00000 0.03544 0.03819 = 0.03715 -0.01385 0.00419 -0.01706 C11 1 0.315042 0.666356 0.713815 11.00000 0.04353 0.03583 = 0.04733 -0.01216 0.00365 -0.01962 AFIX 43 H11 2 0.389945 0.704320 0.681690 11.00000 -1.20000 AFIX 0 C5 1 0.395216 0.167311 0.739564 11.00000 0.04473 0.03957 = 0.03546 -0.01258 0.00167 -0.02360 C6 1 0.296831 0.268187 0.820768 11.00000 0.04161 0.04154 = 0.04063 -0.01294 0.00246 -0.02429 C13 1 0.453145 0.228503 0.607965 11.00000 0.04498 0.03427 = 0.04580 -0.01451 0.00423 -0.01932 C16 1 0.810182 0.296467 0.669533 11.00000 0.03600 0.04852 = 0.04389 -0.01108 0.00085 -0.02053 C10 1 0.159667 0.776281 0.729409 11.00000 0.05289 0.03501 = 0.05269 -0.01551 0.00448 -0.01308 AFIX 43 H10 2 0.128601 0.889260 0.708912 11.00000 -1.20000 AFIX 0 C8 1 0.094992 0.557343 0.803834 11.00000 0.04010 0.04970 = 0.05452 -0.01766 0.00914 -0.02083 AFIX 43 H8 2 0.018395 0.521100 0.833757 11.00000 -1.20000 AFIX 0 C4 1 0.429617 0.003628 0.770102 11.00000 0.05695 0.03966 = 0.05197 -0.01517 0.00241 -0.02547 AFIX 43 H4 2 0.494552 -0.063423 0.713481 11.00000 -1.20000 AFIX 0 C9 1 0.050761 0.722013 0.774415 11.00000 0.03741 0.04880 = 0.06336 -0.02224 0.00924 -0.01233 AFIX 43 H9 2 -0.055423 0.797577 0.785477 11.00000 -1.20000 AFIX 0 C1 1 0.234586 0.200288 0.931724 11.00000 0.05690 0.05202 = 0.04674 -0.01534 0.01101 -0.03233 AFIX 43 H1 2 0.165927 0.267095 0.987044 11.00000 -1.20000 AFIX 0 C3 1 0.368905 -0.060388 0.882890 11.00000 0.06950 0.04111 = 0.05972 -0.00976 0.00036 -0.03194 AFIX 43 H3 2 0.394940 -0.172234 0.905242 11.00000 -1.20000 AFIX 0 C2 1 0.270624 0.038140 0.962837 11.00000 0.06879 0.05468 = 0.05808 -0.00620 0.00785 -0.04052 AFIX 43 H2 2 0.227685 -0.005533 1.039350 11.00000 -1.20000 AFIX 0 C17 1 1.048682 0.250923 0.562291 11.00000 0.03608 0.09016 = 0.07290 -0.02578 0.01505 -0.02409 AFIX 137 H17A 2 1.099369 0.312288 0.506796 11.00000 -1.50000 H17B 2 1.042670 0.178549 0.513625 11.00000 -1.50000 H17C 2 1.111413 0.186032 0.647941 11.00000 -1.50000 AFIX 0 HKLF 4 REM hubu-lyj-tpt-jacs-20190512_a.res in P-1 REM R1 = 0.0378 for 3043 Fo > 4sig(Fo) and 0.0413 for all 3261 data REM 200 parameters refined using 0 restraints END WGHT 0.0607 0.8048 REM Highest difference peak 1.049, deepest hole -1.272, 1-sigma level 0.095 Q1 1 0.6094 0.4811 0.9028 11.00000 0.05 1.05 Q2 1 0.7149 0.5239 0.8227 11.00000 0.05 1.01 Q3 1 0.8180 0.4570 0.8570 11.00000 0.05 1.00 Q4 1 0.7305 0.4521 0.9736 11.00000 0.05 0.52 Q5 1 0.6353 0.4549 1.0115 11.00000 0.05 0.48 Q6 1 0.7551 0.3947 0.8828 11.00000 0.05 0.37 Q7 1 0.4629 0.5227 0.9145 11.00000 0.05 0.33 Q8 1 0.5441 0.1264 0.5549 11.00000 0.05 0.32 Q9 1 0.4008 0.2040 0.6680 11.00000 0.05 0.31 Q10 1 0.7764 0.4569 0.7636 11.00000 0.05 0.31 Q11 1 0.5924 0.4135 0.7200 11.00000 0.05 0.27 Q12 1 -0.0410 0.3954 0.8418 11.00000 0.05 0.26 Q13 1 0.2899 0.2275 0.8935 11.00000 0.05 0.25 Q14 1 0.6462 0.4079 0.6685 11.00000 0.05 0.25 Q15 1 0.1995 0.7393 0.6836 11.00000 0.05 0.25 Q16 1 0.1871 0.0379 1.0805 11.00000 0.05 0.25 Q17 1 -0.0558 0.4225 0.8754 11.00000 0.05 0.25 Q18 1 -0.0993 0.5047 0.7630 11.00000 0.05 0.24 Q19 1 0.9995 0.3177 0.4211 11.00000 0.05 0.24 Q20 1 0.3764 0.7257 0.7832 11.00000 0.05 0.24 ; _shelx_res_checksum 61141 _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 1.623 _oxdiff_exptl_absorpt_empirical_full_min 0.664 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 I1 I 0.70697(3) 0.46562(3) 0.88738(3) 0.05572(13) Uani 1 1 d . . . . . O2 O 0.5173(3) 0.3284(3) 0.6031(2) 0.0386(5) Uani 1 1 d . . . . . O4 O 0.8896(3) 0.3633(4) 0.5897(3) 0.0528(7) Uani 1 1 d . . . . . O1 O 0.4451(4) 0.1936(4) 0.5057(3) 0.0576(8) Uani 1 1 d . . . . . O3 O 0.8557(4) 0.1532(3) 0.7125(4) 0.0654(9) Uani 1 1 d . . . . . C14 C 0.5269(4) 0.3743(4) 0.7256(3) 0.0340(6) Uani 1 1 d . . . . . H14 H 0.5612 0.2767 0.8046 0.041 Uiso 1 1 calc R . . . . C12 C 0.3614(4) 0.5010(4) 0.7450(3) 0.0350(7) Uani 1 1 d . . . . . C15 C 0.6555(4) 0.4273(4) 0.7021(3) 0.0359(7) Uani 1 1 d . . . . . H15 H 0.6194 0.5298 0.6279 0.043 Uiso 1 1 calc R . . . . C7 C 0.2507(4) 0.4446(4) 0.7899(4) 0.0362(7) Uani 1 1 d . . . . . C11 C 0.3150(4) 0.6664(4) 0.7138(4) 0.0415(8) Uani 1 1 d . . . . . H11 H 0.3899 0.7043 0.6817 0.050 Uiso 1 1 calc R . . . . C5 C 0.3952(4) 0.1673(4) 0.7396(4) 0.0376(7) Uani 1 1 d . . . . . C6 C 0.2968(4) 0.2682(4) 0.8208(4) 0.0387(7) Uani 1 1 d . . . . . C13 C 0.4531(4) 0.2285(4) 0.6080(4) 0.0406(7) Uani 1 1 d . . . . . C16 C 0.8102(4) 0.2965(5) 0.6695(4) 0.0426(8) Uani 1 1 d . . . . . C10 C 0.1597(5) 0.7763(4) 0.7294(4) 0.0492(9) Uani 1 1 d . . . . . H10 H 0.1286 0.8893 0.7089 0.059 Uiso 1 1 calc R . . . . C8 C 0.0950(5) 0.5573(5) 0.8038(4) 0.0477(8) Uani 1 1 d . . . . . H8 H 0.0184 0.5211 0.8338 0.057 Uiso 1 1 calc R . . . . C4 C 0.4296(5) 0.0036(4) 0.7701(4) 0.0476(9) Uani 1 1 d . . . . . H4 H 0.4946 -0.0634 0.7135 0.057 Uiso 1 1 calc R . . . . C9 C 0.0508(5) 0.7220(5) 0.7744(5) 0.0518(9) Uani 1 1 d . . . . . H9 H -0.0554 0.7976 0.7855 0.062 Uiso 1 1 calc R . . . . C1 C 0.2346(5) 0.2003(5) 0.9317(4) 0.0489(9) Uani 1 1 d . . . . . H1 H 0.1659 0.2671 0.9870 0.059 Uiso 1 1 calc R . . . . C3 C 0.3689(6) -0.0604(5) 0.8829(5) 0.0547(10) Uani 1 1 d . . . . . H3 H 0.3949 -0.1722 0.9052 0.066 Uiso 1 1 calc R . . . . C2 C 0.2706(6) 0.0381(5) 0.9628(5) 0.0577(10) Uani 1 1 d . . . . . H2 H 0.2277 -0.0055 1.0393 0.069 Uiso 1 1 calc R . . . . C17 C 1.0487(5) 0.2509(7) 0.5623(6) 0.0683(13) Uani 1 1 d . . . . . H17A H 1.0994 0.3123 0.5068 0.102 Uiso 1 1 calc GR . . . . H17B H 1.0427 0.1785 0.5136 0.102 Uiso 1 1 calc GR . . . . H17C H 1.1114 0.1860 0.6479 0.102 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 I1 0.05307(19) 0.0788(2) 0.0530(2) -0.02830(14) 0.00532(12) -0.03956(15) O2 0.0438(13) 0.0404(11) 0.0390(13) -0.0153(10) 0.0080(10) -0.0239(10) O4 0.0404(14) 0.0613(16) 0.0550(17) -0.0124(13) 0.0097(12) -0.0248(12) O1 0.091(2) 0.0622(16) 0.0428(15) -0.0272(13) 0.0141(15) -0.0494(17) O3 0.0499(16) 0.0394(14) 0.093(3) -0.0129(14) 0.0142(16) -0.0135(12) C14 0.0351(16) 0.0338(14) 0.0353(16) -0.0109(12) 0.0027(13) -0.0169(12) C12 0.0376(16) 0.0350(15) 0.0337(16) -0.0133(12) 0.0024(13) -0.0158(13) C15 0.0390(17) 0.0385(15) 0.0345(17) -0.0114(13) 0.0021(13) -0.0205(13) C7 0.0354(16) 0.0382(15) 0.0372(17) -0.0139(13) 0.0042(13) -0.0171(13) C11 0.0435(18) 0.0358(15) 0.047(2) -0.0122(14) 0.0037(15) -0.0196(14) C5 0.0447(18) 0.0396(16) 0.0355(17) -0.0126(13) 0.0017(14) -0.0236(14) C6 0.0416(17) 0.0415(16) 0.0406(18) -0.0129(14) 0.0025(14) -0.0243(14) C13 0.0450(18) 0.0343(15) 0.046(2) -0.0145(14) 0.0042(15) -0.0193(14) C16 0.0360(17) 0.0485(18) 0.044(2) -0.0111(15) 0.0008(14) -0.0205(15) C10 0.053(2) 0.0350(16) 0.053(2) -0.0155(15) 0.0045(17) -0.0131(15) C8 0.0401(19) 0.0497(19) 0.055(2) -0.0177(17) 0.0091(16) -0.0208(16) C4 0.057(2) 0.0397(17) 0.052(2) -0.0152(16) 0.0024(17) -0.0255(16) C9 0.0374(18) 0.0488(19) 0.063(3) -0.0222(18) 0.0092(17) -0.0123(15) C1 0.057(2) 0.052(2) 0.047(2) -0.0153(17) 0.0110(17) -0.0323(18) C3 0.070(3) 0.0411(18) 0.060(3) -0.0098(17) 0.000(2) -0.0319(18) C2 0.069(3) 0.055(2) 0.058(3) -0.0062(19) 0.008(2) -0.041(2) C17 0.036(2) 0.090(3) 0.073(3) -0.026(3) 0.015(2) -0.024(2) 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' 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C13 O2 C14 118.9(3) . . ? C16 O4 C17 115.8(3) . . ? O2 C14 C12 106.9(3) . . ? O2 C14 C15 104.8(3) . . ? C12 C14 C15 117.0(3) . . ? C7 C12 C14 116.5(3) . . ? C11 C12 C14 123.3(3) . . ? C11 C12 C7 120.2(3) . . ? C14 C15 I1 108.9(2) . . ? C16 C15 I1 105.4(2) . . ? C16 C15 C14 111.9(3) . . ? C12 C7 C6 121.1(3) . . ? C8 C7 C12 118.6(3) . . ? C8 C7 C6 120.2(3) . . ? C10 C11 C12 120.2(3) . . ? C6 C5 C13 123.5(3) . . ? C4 C5 C6 120.5(3) . . ? C4 C5 C13 115.6(3) . . ? C5 C6 C7 122.8(3) . . ? C1 C6 C7 119.2(3) . . ? C1 C6 C5 117.9(3) . . ? O2 C13 C5 119.0(3) . . ? O1 C13 O2 117.8(3) . . ? O1 C13 C5 123.2(3) . . ? O4 C16 C15 110.0(3) . . ? O3 C16 O4 125.2(4) . . ? O3 C16 C15 124.7(3) . . ? C9 C10 C11 120.1(3) . . ? C9 C8 C7 120.6(4) . . ? C3 C4 C5 120.0(4) . . ? C10 C9 C8 120.3(3) . . ? C2 C1 C6 121.5(4) . . ? C2 C3 C4 120.1(4) . . ? C3 C2 C1 120.1(4) . . ? 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 I1 C15 2.157(3) . ? O2 C14 1.457(4) . ? O2 C13 1.352(4) . ? O4 C16 1.324(5) . ? O4 C17 1.451(5) . ? O1 C13 1.199(5) . ? O3 C16 1.198(5) . ? C14 C12 1.514(4) . ? C14 C15 1.520(5) . ? C12 C7 1.401(5) . ? C12 C11 1.388(5) . ? C15 C16 1.508(5) . ? C7 C6 1.489(5) . ? C7 C8 1.394(5) . ? C11 C10 1.387(5) . ? C5 C6 1.401(5) . ? C5 C13 1.501(5) . ? C5 C4 1.401(5) . ? C6 C1 1.397(5) . ? C10 C9 1.372(6) . ? C8 C9 1.387(6) . ? C4 C3 1.385(6) . ? C1 C2 1.382(6) . ? C3 C2 1.380(7) . ?