#------------------------------------------------------------------------------ #$Date: 2020-07-06 05:03:52 +0300 (Mon, 06 Jul 2020) $ #$Revision: 253819 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/64/7126467.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_7126467 loop_ _publ_author_name 'Tang, Pan-Ting' 'Shao, You-Xiang' 'Wang, Liang-Neng' '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_issue 49 _journal_name_full 'Chemical communications (Cambridge, England)' _journal_page_first 6680 _journal_page_last 6683 _journal_paper_doi 10.1039/c9cc10080f _journal_volume 56 _journal_year 2020 _chemical_formula_moiety 'C19 H15 I O4' _chemical_formula_sum 'C19 H15 I O4' _chemical_formula_weight 434.21 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2019-06-14 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-07-31 deposited with the CCDC. 2020-04-30 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 95.488(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.09310(10) _cell_length_b 13.1306(2) _cell_length_c 15.5266(2) _cell_measurement_reflns_used 5993 _cell_measurement_temperature 99.98(10) _cell_measurement_theta_max 75.7390 _cell_measurement_theta_min 4.4070 _cell_volume 1642.41(4) _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 99.98(10) _diffrn_detector 'CCD plate' _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _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 22.00 48.00 0.50 0.05 -- 43.18 57.00 120.00 52 2 \w 62.00 114.00 0.50 0.05 -- 43.18 57.00 120.00 104 3 \w 91.00 173.00 0.50 0.06 -- 109.88 45.00 -60.00 164 4 \w 114.00 139.00 0.50 0.06 -- 109.88 115.00-157.00 50 5 \w 97.00 166.00 0.50 0.06 -- 109.88 125.00-180.00 138 6 \w 133.00 159.00 0.50 0.06 -- 109.88 45.00-180.00 52 7 \w 90.00 126.00 0.50 0.06 -- 109.88 45.00-180.00 72 8 \w 88.00 178.00 0.50 0.06 -- 109.88 61.00 -90.00 180 9 \w 85.00 137.00 0.50 0.06 -- 109.88 -77.00 90.00 104 10 \w 83.00 146.00 0.50 0.06 -- 109.88-166.00 -33.00 126 11 \w 34.00 59.00 0.50 0.05 -- 43.18-115.00 113.00 50 12 \w 48.00 109.00 0.50 0.06 -- 109.88-115.00 113.00 122 13 \w 37.00 108.00 0.50 0.06 -- 109.88 -94.00 -30.00 142 14 \w -93.00 -47.00 0.50 0.05 -- -43.18-166.00 -33.00 92 15 \w -64.00 -38.00 0.50 0.06 -- -90.25 61.00 30.00 52 16 \w -99.00 -74.00 0.50 0.05 -- -43.18 166.00 -11.00 50 17 \w -99.00 -74.00 0.50 0.06 -- -90.25 166.00 -11.00 50 18 \w -88.00 -8.00 0.50 0.05 -- -43.18 115.00-157.00 160 19 \w -77.00 -52.00 0.50 0.06 -- -90.25 115.00-157.00 50 20 \w -109.00 -18.00 0.50 0.05 -- -43.18 -77.00 30.00 182 21 \w -139.00 -83.00 0.50 0.06 -- -90.25-115.00 113.00 112 ; _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 -0.0691118000 _diffrn_orient_matrix_UB_12 -0.1070727000 _diffrn_orient_matrix_UB_13 -0.0225744000 _diffrn_orient_matrix_UB_21 -0.1066144000 _diffrn_orient_matrix_UB_22 0.0442284000 _diffrn_orient_matrix_UB_23 -0.0786396000 _diffrn_orient_matrix_UB_31 0.1428805000 _diffrn_orient_matrix_UB_32 -0.0186191000 _diffrn_orient_matrix_UB_33 -0.0569399000 _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 0.0495 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 9809 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 67.074 _diffrn_reflns_theta_max 67.074 _diffrn_reflns_theta_min 4.418 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 15.498 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.18255 _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 1.756 _exptl_crystal_description block _exptl_crystal_F_000 856 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _refine_diff_density_max 1.872 _refine_diff_density_min -2.405 _refine_diff_density_rms 0.283 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 218 _refine_ls_number_reflns 2932 _refine_ls_number_restraints 62 _refine_ls_restrained_S_all 1.059 _refine_ls_R_factor_all 0.0512 _refine_ls_R_factor_gt 0.0449 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0891P)^2^+1.4317P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1206 _refine_ls_wR_factor_ref 0.1260 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2753 _reflns_number_total 2932 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9cc10080f2.cif _cod_data_source_block hubu-lyj-tpt-i _cod_depositor_comments 'Adding full bibliography for 7126465--7126470.cif.' _cod_database_code 7126467 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'I C N H O' _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 0.148 _shelx_estimated_absorpt_t_min 0.148 _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. Rigid bond restraints All non-hydrogen atoms with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001 3.a Ternary CH refined with riding coordinates: C3(H3), C4(H4) 3.b Aromatic/amide H refined with riding coordinates: C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19) 3.c Idealised Me refined as rotating group: C1(H1A,H1B,H1C) ; _shelx_res_file ; TITL hubu-lyj-tpt-i_a.res in P2(1)/n hubu-lyj-tpt-i.res created by SHELXL-2018/3 at 17:57:10 on 14-Jun-2019 REM Old TITL hubu-lyj-tpt-i_a.res in P2(1) REM SHELXT solution in P2(1)/n: R1 0.090, Rweak 0.003, Alpha 0.113 REM 0.967 for 157 systematic absences, Orientation as input REM Formula found by SHELXT: C19 I O4 CELL 1.54184 8.0931 13.1306 15.5266 90 95.488 90 ZERR 4 0.0001 0.0002 0.0002 0 0.002 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H I O UNIT 76 60 4 16 DELU 0.001 0.001 L.S. 4 0 0 PLAN 20 SIZE 0.2 0.2 0.2 BOND list 4 fmap 2 53 acta SHEL 999 0.837 OMIT -8 6 9 OMIT 6 5 12 REM REM REM WGHT 0.089100 1.431700 FVAR 0.24739 I1 3 0.654276 0.121858 0.611169 11.00000 0.01475 0.01237 = 0.01367 0.00438 0.00043 0.00263 O1 4 0.244402 0.178734 0.551658 11.00000 0.01391 0.02096 = 0.03763 0.00654 0.00404 -0.00167 O2 4 0.382772 0.327669 0.554056 11.00000 0.01629 0.01599 = 0.02101 0.00214 0.00275 0.00176 O3 4 0.481339 0.274266 0.371292 11.00000 0.01529 0.01302 = 0.00966 -0.00031 -0.00380 -0.00217 O4 4 0.401843 0.385042 0.269240 11.00000 0.02086 0.01963 = 0.01013 0.00096 -0.00260 0.00452 C1 1 0.121399 0.227500 0.600889 11.00000 0.02447 0.03442 = 0.04723 0.02000 0.01786 0.00851 AFIX 137 H1A 2 0.074245 0.284947 0.569144 11.00000 -1.50000 H1B 2 0.173802 0.249999 0.655670 11.00000 -1.50000 H1C 2 0.035256 0.179624 0.610230 11.00000 -1.50000 AFIX 0 C2 1 0.371041 0.237988 0.536729 11.00000 0.01218 0.01583 = 0.01167 0.00486 -0.00405 -0.00109 C3 1 0.505052 0.177729 0.498040 11.00000 0.01307 0.01000 = 0.01408 0.00244 -0.00264 -0.00293 AFIX 13 H3 2 0.456069 0.120698 0.463791 11.00000 -1.20000 AFIX 0 C4 1 0.605014 0.245741 0.442186 11.00000 0.01273 0.00737 = 0.01340 0.00245 -0.00241 -0.00056 AFIX 13 H4 2 0.639630 0.307012 0.475158 11.00000 -1.20000 AFIX 0 C5 1 0.753302 0.201042 0.404857 11.00000 0.01572 0.00964 = 0.00905 -0.00178 -0.00153 -0.00117 C6 1 0.788850 0.097395 0.405545 11.00000 0.02271 0.00967 = 0.01646 -0.00175 0.00178 0.00069 AFIX 43 H6 2 0.718823 0.052104 0.430346 11.00000 -1.20000 AFIX 0 C7 1 0.927726 0.060917 0.369600 11.00000 0.02760 0.01305 = 0.02342 -0.00149 0.00512 0.00537 AFIX 43 H7 2 0.950688 -0.008494 0.370841 11.00000 -1.20000 AFIX 0 C8 1 1.031982 0.127245 0.331994 11.00000 0.02512 0.01955 = 0.02444 0.00029 0.00839 0.00767 AFIX 43 H8 2 1.124682 0.102323 0.307804 11.00000 -1.20000 AFIX 0 C9 1 0.998909 0.231182 0.330147 11.00000 0.01731 0.01694 = 0.01684 0.00010 0.00337 0.00125 AFIX 43 H9 2 1.071258 0.275432 0.305859 11.00000 -1.20000 AFIX 0 C10 1 0.857625 0.270090 0.364508 11.00000 0.01533 0.01158 = 0.01004 0.00103 -0.00115 0.00088 C11 1 0.818726 0.380275 0.357629 11.00000 0.01913 0.01175 = 0.00983 0.00270 0.00098 0.00049 C12 1 0.662678 0.417795 0.344954 11.00000 0.01918 0.00895 = 0.00971 -0.00005 0.00140 0.00078 AFIX 43 H12 2 0.651768 0.488051 0.349457 11.00000 -1.20000 AFIX 0 C13 1 0.508336 0.359842 0.324841 11.00000 0.01816 0.01023 = 0.00791 -0.00095 -0.00060 0.00312 C14 1 0.961725 0.452246 0.359474 11.00000 0.01805 0.00977 = 0.00843 -0.00169 0.00261 0.00188 C15 1 1.098384 0.440644 0.420043 11.00000 0.01743 0.01702 = 0.01407 0.00400 0.00178 0.00172 AFIX 43 H15 2 1.100626 0.387500 0.459733 11.00000 -1.20000 AFIX 0 C16 1 1.231685 0.507559 0.421954 11.00000 0.01874 0.01818 = 0.01426 -0.00375 0.00004 0.00003 AFIX 43 H16 2 1.321368 0.499755 0.463558 11.00000 -1.20000 AFIX 0 C17 1 1.231546 0.585719 0.362243 11.00000 0.01882 0.01293 = 0.01951 -0.00496 0.00521 -0.00239 AFIX 43 H17 2 1.321313 0.630074 0.363350 11.00000 -1.20000 AFIX 0 C18 1 1.096806 0.597742 0.300589 11.00000 0.02047 0.01225 = 0.02044 0.00238 0.00511 0.00056 AFIX 43 H18 2 1.096163 0.650156 0.260273 11.00000 -1.20000 AFIX 0 C19 1 0.963718 0.531592 0.299333 11.00000 0.01969 0.01067 = 0.01659 0.00314 -0.00041 0.00072 AFIX 43 H19 2 0.873988 0.539930 0.257840 11.00000 -1.20000 AFIX 0 HKLF 4 REM hubu-lyj-tpt-i_a.res in P2(1)/n REM wR2 = 0.1260, GooF = S = 1.068, Restrained GooF = 1.059 for all data REM R1 = 0.0449 for 2753 Fo > 4sig(Fo) and 0.0512 for all 2932 data REM 218 parameters refined using 62 restraints END WGHT 0.0891 1.4317 REM Highest difference peak 1.872, deepest hole -2.405, 1-sigma level 0.283 Q1 1 0.7747 0.1033 0.6040 11.00000 0.05 1.87 Q2 1 0.5235 0.1079 0.6200 11.00000 0.05 1.78 Q3 1 0.5831 -0.0454 0.3935 11.00000 0.05 1.24 Q4 1 -0.1041 0.1980 0.6192 11.00000 0.05 1.18 Q5 1 0.2912 0.2532 0.5616 11.00000 0.05 1.09 Q6 1 1.1074 -0.0455 0.3817 11.00000 0.05 1.09 Q7 1 0.4297 0.1990 0.6157 11.00000 0.05 1.00 Q8 1 0.5417 0.0443 0.6023 11.00000 0.05 0.99 Q9 1 0.3431 0.1227 0.6216 11.00000 0.05 0.91 Q10 1 0.0994 0.1197 0.6117 11.00000 0.05 0.90 Q11 1 0.5214 0.0454 0.3936 11.00000 0.05 0.86 Q12 1 0.7814 0.0041 0.3794 11.00000 0.05 0.81 Q13 1 0.6613 0.0031 0.3758 11.00000 0.05 0.80 Q14 1 0.6350 0.0398 0.5586 11.00000 0.05 0.80 Q15 1 0.2828 0.1819 0.5989 11.00000 0.05 0.80 Q16 1 -0.0278 0.1191 0.6178 11.00000 0.05 0.79 Q17 1 1.3238 0.0955 0.3576 11.00000 0.05 0.76 Q18 1 0.8417 -0.0604 0.3934 11.00000 0.05 0.76 Q19 1 0.8443 0.0832 0.3801 11.00000 0.05 0.75 Q20 1 0.6897 0.2016 0.6614 11.00000 0.05 0.74 ; _shelx_res_checksum 77517 _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 2.759 _oxdiff_exptl_absorpt_empirical_full_min 0.590 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -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 I1 I 0.65428(3) 0.12186(2) 0.61117(2) 0.01366(16) Uani 1 1 d . U . . . O1 O 0.2444(4) 0.1787(3) 0.5517(2) 0.0241(7) Uani 1 1 d . U . . . O2 O 0.3828(4) 0.3277(2) 0.55406(19) 0.0177(6) Uani 1 1 d . U . . . O3 O 0.4813(3) 0.2743(2) 0.37129(17) 0.0130(5) Uani 1 1 d . U . . . O4 O 0.4018(4) 0.3850(2) 0.2692(2) 0.0171(7) Uani 1 1 d . U . . . C1 C 0.1214(7) 0.2275(5) 0.6009(4) 0.0344(13) Uani 1 1 d . U . . . H1A H 0.074245 0.284947 0.569144 0.052 Uiso 1 1 calc GR . . . . H1B H 0.173802 0.249999 0.655670 0.052 Uiso 1 1 calc GR . . . . H1C H 0.035256 0.179624 0.610230 0.052 Uiso 1 1 calc GR . . . . C2 C 0.3710(5) 0.2380(3) 0.5367(3) 0.0136(6) Uani 1 1 d . U . . . C3 C 0.5051(5) 0.1777(3) 0.4980(3) 0.0126(6) Uani 1 1 d . U . . . H3 H 0.456069 0.120698 0.463791 0.015 Uiso 1 1 calc R . . . . C4 C 0.6050(5) 0.2457(3) 0.4422(3) 0.0114(6) Uani 1 1 d . U . . . H4 H 0.639630 0.307012 0.475158 0.014 Uiso 1 1 calc R . . . . C5 C 0.7533(5) 0.2010(3) 0.4049(2) 0.0116(6) Uani 1 1 d . U . . . C6 C 0.7889(6) 0.0974(4) 0.4055(3) 0.0163(8) Uani 1 1 d . U . . . H6 H 0.718823 0.052104 0.430346 0.020 Uiso 1 1 calc R . . . . C7 C 0.9277(6) 0.0609(4) 0.3696(3) 0.0212(8) Uani 1 1 d . U . . . H7 H 0.950688 -0.008494 0.370841 0.025 Uiso 1 1 calc R . . . . C8 C 1.0320(7) 0.1272(3) 0.3320(4) 0.0227(10) Uani 1 1 d . U . . . H8 H 1.124682 0.102323 0.307804 0.027 Uiso 1 1 calc R . . . . C9 C 0.9989(5) 0.2312(4) 0.3301(3) 0.0169(8) Uani 1 1 d . U . . . H9 H 1.071258 0.275432 0.305859 0.020 Uiso 1 1 calc R . . . . C10 C 0.8576(5) 0.2701(3) 0.3645(3) 0.0125(6) Uani 1 1 d . U . . . C11 C 0.8187(6) 0.3803(3) 0.3576(3) 0.0136(7) Uani 1 1 d . U . . . C12 C 0.6627(5) 0.4178(3) 0.3450(2) 0.0126(6) Uani 1 1 d . U . . . H12 H 0.651768 0.488051 0.349457 0.015 Uiso 1 1 calc R . . . . C13 C 0.5083(6) 0.3598(3) 0.3248(3) 0.0122(7) Uani 1 1 d . U . . . C14 C 0.9617(5) 0.4522(3) 0.3595(2) 0.0120(6) Uani 1 1 d . U . . . C15 C 1.0984(5) 0.4406(3) 0.4200(3) 0.0162(7) Uani 1 1 d . U . . . H15 H 1.100626 0.387500 0.459733 0.019 Uiso 1 1 calc R . . . . C16 C 1.2317(5) 0.5076(3) 0.4220(3) 0.0172(7) Uani 1 1 d . U . . . H16 H 1.321368 0.499755 0.463558 0.021 Uiso 1 1 calc R . . . . C17 C 1.2315(5) 0.5857(3) 0.3622(3) 0.0169(7) Uani 1 1 d . U . . . H17 H 1.321313 0.630074 0.363350 0.020 Uiso 1 1 calc R . . . . C18 C 1.0968(6) 0.5977(4) 0.3006(3) 0.0175(8) Uani 1 1 d . U . . . H18 H 1.096163 0.650156 0.260273 0.021 Uiso 1 1 calc R . . . . C19 C 0.9637(5) 0.5316(3) 0.2993(3) 0.0158(7) Uani 1 1 d . U . . . H19 H 0.873988 0.539930 0.257840 0.019 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 I1 0.0148(2) 0.0124(2) 0.0137(2) 0.00438(8) 0.00043(14) 0.00263(8) O1 0.0139(13) 0.0210(15) 0.0376(18) 0.0065(14) 0.0040(12) -0.0017(11) O2 0.0163(15) 0.0160(11) 0.0210(15) 0.0021(12) 0.0028(12) 0.0018(10) O3 0.0153(12) 0.0130(13) 0.0097(11) -0.0003(8) -0.0038(10) -0.0022(10) O4 0.0209(15) 0.0196(16) 0.0101(15) 0.0010(9) -0.0026(10) 0.0045(11) C1 0.024(2) 0.034(3) 0.047(3) 0.020(2) 0.0179(19) 0.009(2) C2 0.0122(13) 0.0158(13) 0.0117(17) 0.0049(13) -0.0040(10) -0.0011(9) C3 0.0131(14) 0.0100(15) 0.0141(15) 0.0024(11) -0.0026(9) -0.0029(11) C4 0.0127(15) 0.0074(15) 0.0134(15) 0.0025(11) -0.0024(9) -0.0006(11) C5 0.0157(13) 0.0096(11) 0.0091(17) -0.0018(13) -0.0015(11) -0.0012(11) C6 0.023(2) 0.0097(11) 0.016(2) -0.0017(16) 0.0018(15) 0.0007(14) C7 0.028(2) 0.0130(15) 0.023(2) -0.0015(17) 0.0051(17) 0.0054(14) C8 0.025(2) 0.0196(17) 0.024(3) 0.0003(16) 0.0084(19) 0.0077(14) C9 0.0173(18) 0.0169(14) 0.017(2) 0.0001(16) 0.0034(14) 0.0013(13) C10 0.0153(16) 0.0116(11) 0.0100(17) 0.0010(14) -0.0012(12) 0.0009(10) C11 0.0191(11) 0.0118(12) 0.010(2) 0.0027(12) 0.0010(15) 0.0005(8) C12 0.0192(11) 0.0090(16) 0.0097(17) 0.0000(15) 0.0014(13) 0.0008(9) C13 0.0182(13) 0.0102(16) 0.0079(17) -0.0010(11) -0.0006(12) 0.0031(12) C14 0.0180(13) 0.0098(14) 0.0084(16) -0.0017(12) 0.0026(11) 0.0019(12) C15 0.0174(16) 0.0170(19) 0.0141(18) 0.0040(14) 0.0018(12) 0.0017(13) C16 0.0187(16) 0.018(2) 0.0143(18) -0.0037(13) 0.0000(13) 0.0000(14) C17 0.0188(17) 0.0129(19) 0.0195(19) -0.0050(14) 0.0052(13) -0.0024(15) C18 0.0205(19) 0.0123(18) 0.020(2) 0.0024(15) 0.0051(14) 0.0006(14) C19 0.0197(17) 0.0107(18) 0.0166(18) 0.0031(13) -0.0004(13) 0.0007(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' 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 C2 O1 C1 114.3(4) . . ? C13 O3 C4 118.4(3) . . ? O1 C2 C3 111.0(4) . . ? O2 C2 O1 125.3(4) . . ? O2 C2 C3 123.6(4) . . ? C2 C3 I1 102.8(2) . . ? C2 C3 C4 111.0(3) . . ? C4 C3 I1 112.0(3) . . ? O3 C4 C3 102.4(3) . . ? O3 C4 C5 108.9(3) . . ? C5 C4 C3 118.5(3) . . ? C6 C5 C4 123.5(4) . . ? C6 C5 C10 119.7(4) . . ? C10 C5 C4 116.8(4) . . ? C7 C6 C5 120.6(4) . . ? C8 C7 C6 120.3(5) . . ? C7 C8 C9 120.2(5) . . ? C8 C9 C10 120.8(4) . . ? C5 C10 C11 121.5(4) . . ? C9 C10 C5 118.3(4) . . ? C9 C10 C11 120.2(4) . . ? C10 C11 C14 117.2(4) . . ? C12 C11 C10 123.7(4) . . ? C12 C11 C14 118.9(4) . . ? C11 C12 C13 127.2(4) . . ? O3 C13 C12 119.3(4) . . ? O4 C13 O3 117.7(4) . . ? O4 C13 C12 123.0(4) . . ? C15 C14 C11 120.6(4) . . ? C15 C14 C19 118.3(4) . . ? C19 C14 C11 121.1(4) . . ? C16 C15 C14 120.7(4) . . ? C17 C16 C15 120.3(4) . . ? C16 C17 C18 119.8(4) . . ? C19 C18 C17 119.8(4) . . ? C18 C19 C14 121.1(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 C3 2.162(4) . ? O1 C1 1.460(6) . ? O1 C2 1.325(5) . ? O2 C2 1.210(5) . ? O3 C4 1.464(5) . ? O3 C13 1.364(5) . ? O4 C13 1.206(6) . ? C2 C3 1.513(6) . ? C3 C4 1.529(5) . ? C4 C5 1.501(6) . ? C5 C6 1.391(6) . ? C5 C10 1.424(6) . ? C6 C7 1.387(7) . ? C7 C8 1.380(7) . ? C8 C9 1.391(6) . ? C9 C10 1.403(6) . ? C10 C11 1.482(6) . ? C11 C12 1.352(7) . ? C11 C14 1.492(6) . ? C12 C13 1.470(6) . ? C14 C15 1.390(6) . ? C14 C19 1.400(6) . ? C15 C16 1.389(6) . ? C16 C17 1.383(6) . ? C17 C18 1.390(7) . ? C18 C19 1.382(6) . ?