#------------------------------------------------------------------------------ #$Date: 2020-05-01 01:01:38 +0300 (Fri, 01 May 2020) $ #$Revision: 251333 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/64/7126470.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_7126470 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 'C19 H17 I O4' _chemical_formula_sum 'C19 H17 I O4' _chemical_formula_weight 436.22 _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 107.437(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.5655(4) _cell_length_b 14.9260(5) _cell_length_c 11.4963(4) _cell_measurement_reflns_used 7217 _cell_measurement_temperature 99.99(10) _cell_measurement_theta_max 29.4440 _cell_measurement_theta_min 2.2890 _cell_volume 1729.66(11) _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 99.99(10) _diffrn_detector 'CCD plate' _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.816 _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 -39.00 65.00 0.50 0.96 -- -9.20 78.00 -9.00 208 2 \w -40.00 14.00 0.50 0.96 -- -9.20 -57.00 150.00 108 3 \w -26.00 17.00 0.50 0.96 -- -9.20 -99.00 90.00 86 4 \w -12.00 17.00 0.50 0.96 -- -9.20 -99.00 30.00 58 5 \w -24.00 17.00 0.50 0.96 -- -9.20 -78.00-134.00 82 6 \w -26.00 13.00 0.50 0.96 -- -9.20 -99.00-180.00 78 ; _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 -0.0581436000 _diffrn_orient_matrix_UB_12 0.0126480000 _diffrn_orient_matrix_UB_13 0.0146759000 _diffrn_orient_matrix_UB_21 -0.0333290000 _diffrn_orient_matrix_UB_22 -0.0382134000 _diffrn_orient_matrix_UB_23 -0.0312372000 _diffrn_orient_matrix_UB_31 0.0214378000 _diffrn_orient_matrix_UB_32 -0.0252714000 _diffrn_orient_matrix_UB_33 0.0546650000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0467 _diffrn_reflns_av_unetI/netI 0.0460 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.816 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 14543 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.816 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 30.305 _diffrn_reflns_theta_min 2.298 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 1.871 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.30254 _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 1.675 _exptl_crystal_description block _exptl_crystal_F_000 864 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.901 _refine_diff_density_min -1.305 _refine_diff_density_rms 0.111 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 220 _refine_ls_number_reflns 4229 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.048 _refine_ls_R_factor_all 0.0449 _refine_ls_R_factor_gt 0.0363 _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^)+(0.0394P)^2^+1.4639P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0854 _refine_ls_wR_factor_ref 0.0900 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3563 _reflns_number_total 4229 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9cc10080f2.cif _cod_data_source_block exp_2639 _cod_database_code 7126470 _shelx_shelxl_version_number 2018/3 _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 0.706 _shelx_estimated_absorpt_t_min 0.706 _reflns_odcompleteness_completeness 99.59 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _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: C3(H3), C4(H4) 2.b Aromatic/amide H refined with riding coordinates: C6(H6), C7(H7), C8(H8), C13(H13), C14(H14), C17(H17) 2.c Idealised Me refined as rotating group: C1(H1A,H1B,H1C), C10(H10A,H10B,H10C), C16(H16A,H16B,H16C) ; _shelx_res_file ; TITL exp_2639_a.res in P2(1)/n exp_2639.res created by SHELXL-2018/3 at 18:02:56 on 14-Jun-2019 REM Old TITL exp_2639 in P2(1)/n REM SHELXT solution in P2(1)/n: R1 0.083, Rweak 0.004, Alpha 0.038 REM 1.200 for 149 systematic absences, Orientation as input REM Formula found by SHELXT: C19 O4 I CELL 0.71073 10.5655 14.926 11.4963 90 107.437 90 ZERR 4 0.0004 0.0005 0.0004 0 0.004 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H I O UNIT 76 68 4 16 L.S. 4 0 0 PLAN 20 SIZE 0.2 0.2 0.2 BOND list 4 fmap 2 53 ACTA REM REM REM WGHT 0.039400 1.463900 FVAR 0.35427 I1 3 0.789248 0.635179 0.121416 11.00000 0.02869 0.03432 = 0.02627 0.00398 0.01236 0.00315 O1 4 0.721589 0.487418 0.317715 11.00000 0.03421 0.02096 = 0.02700 -0.00063 0.00708 0.00611 O2 4 0.613058 0.420581 0.141918 11.00000 0.06081 0.02696 = 0.03973 -0.01131 0.00277 -0.00212 O3 4 0.465890 0.589364 0.269539 11.00000 0.02312 0.01767 = 0.02387 -0.00345 0.00833 -0.00327 O4 4 0.360235 0.563933 0.403573 11.00000 0.03313 0.03301 = 0.03088 -0.00428 0.01513 -0.01401 C1 1 0.768058 0.400747 0.370355 11.00000 0.03779 0.02794 = 0.03317 0.00759 0.01405 0.01311 AFIX 137 H1A 2 0.824456 0.374652 0.327750 11.00000 -1.50000 H1B 2 0.693442 0.362160 0.363335 11.00000 -1.50000 H1C 2 0.817038 0.408050 0.454828 11.00000 -1.50000 AFIX 0 C2 1 0.647136 0.486927 0.202132 11.00000 0.02237 0.02582 = 0.02706 -0.00255 0.01053 0.00225 C3 1 0.611905 0.579630 0.151321 11.00000 0.02545 0.02629 = 0.02004 -0.00500 0.00263 -0.00011 AFIX 13 H3 2 0.541544 0.575736 0.073333 11.00000 -1.20000 AFIX 0 C4 1 0.567984 0.641690 0.236682 11.00000 0.01988 0.02135 = 0.01853 -0.00293 0.00436 -0.00103 AFIX 13 H4 2 0.642639 0.653318 0.309721 11.00000 -1.20000 AFIX 0 C5 1 0.505634 0.729028 0.183099 11.00000 0.01661 0.02061 = 0.02009 -0.00109 0.00464 -0.00122 C6 1 0.462793 0.746505 0.059545 11.00000 0.02311 0.02994 = 0.02110 -0.00341 0.00506 -0.00179 AFIX 43 H6 2 0.476614 0.704513 0.004829 11.00000 -1.20000 AFIX 0 C7 1 0.398992 0.826806 0.016734 11.00000 0.02227 0.03443 = 0.01644 0.00419 -0.00052 -0.00119 AFIX 43 H7 2 0.371527 0.839156 -0.066375 11.00000 -1.20000 AFIX 0 C8 1 0.376707 0.888046 0.098405 11.00000 0.02368 0.02664 = 0.02537 0.00892 0.00357 0.00330 AFIX 43 H8 2 0.332812 0.941209 0.069033 11.00000 -1.20000 AFIX 0 C9 1 0.418117 0.872429 0.223506 11.00000 0.01844 0.02037 = 0.02588 0.00167 0.00720 0.00039 C10 1 0.385263 0.942615 0.305204 11.00000 0.03395 0.01990 = 0.03430 0.00191 0.00796 0.00938 AFIX 137 H10A 2 0.375911 0.914408 0.377225 11.00000 -1.50000 H10B 2 0.303677 0.971845 0.262344 11.00000 -1.50000 H10C 2 0.455383 0.986065 0.327808 11.00000 -1.50000 AFIX 0 C11 1 0.484921 0.791826 0.266871 11.00000 0.01487 0.01787 = 0.01825 0.00156 0.00410 -0.00083 C12 1 0.532763 0.771084 0.399615 11.00000 0.01441 0.01803 = 0.02117 -0.00116 0.00545 0.00228 C13 1 0.602036 0.834804 0.482711 11.00000 0.02107 0.01736 = 0.02498 -0.00075 0.00464 0.00102 AFIX 43 H13 2 0.624535 0.888663 0.453339 11.00000 -1.20000 AFIX 0 C14 1 0.638696 0.821150 0.607201 11.00000 0.02493 0.02306 = 0.02264 -0.00665 0.00229 -0.00138 AFIX 43 H14 2 0.685688 0.865329 0.659594 11.00000 -1.20000 AFIX 0 C15 1 0.605637 0.741230 0.655209 11.00000 0.01847 0.03297 = 0.01899 0.00066 0.00473 0.00502 C16 1 0.637299 0.728353 0.790632 11.00000 0.03061 0.04788 = 0.01886 -0.00065 0.00513 0.00395 AFIX 137 H16A 2 0.731399 0.732912 0.827981 11.00000 -1.50000 H16B 2 0.607466 0.670263 0.806926 11.00000 -1.50000 H16C 2 0.593250 0.773661 0.823457 11.00000 -1.50000 AFIX 0 C17 1 0.542782 0.675033 0.574333 11.00000 0.01609 0.02560 = 0.02270 0.00361 0.00571 0.00328 AFIX 43 H17 2 0.523862 0.620451 0.604433 11.00000 -1.20000 AFIX 0 C18 1 0.506987 0.688418 0.448024 11.00000 0.01367 0.01841 = 0.02128 -0.00067 0.00493 0.00081 C19 1 0.437952 0.610674 0.373890 11.00000 0.01896 0.02021 = 0.02033 0.00170 0.00514 -0.00079 HKLF 4 REM exp_2639_a.res in P2(1)/n REM wR2 = 0.0900, GooF = S = 1.048, Restrained GooF = 1.048 for all data REM R1 = 0.0363 for 3563 Fo > 4sig(Fo) and 0.0449 for all 4229 data REM 220 parameters refined using 0 restraints END WGHT 0.0394 1.4640 REM Highest difference peak 0.901, deepest hole -1.305, 1-sigma level 0.111 Q1 1 0.7372 0.6162 0.0538 11.00000 0.05 0.90 Q2 1 0.7016 0.6604 0.0433 11.00000 0.05 0.83 Q3 1 0.8719 0.6769 0.2006 11.00000 0.05 0.79 Q4 1 0.7958 0.6391 0.2091 11.00000 0.05 0.76 Q5 1 0.8691 0.5884 0.1964 11.00000 0.05 0.62 Q6 1 0.8096 0.6360 0.0223 11.00000 0.05 0.59 Q7 1 0.8871 0.5974 0.1001 11.00000 0.05 0.56 Q8 1 0.6858 0.4194 0.2780 11.00000 0.05 0.52 Q9 1 0.6165 0.8197 0.5421 11.00000 0.05 0.51 Q10 1 0.8825 0.6746 0.0966 11.00000 0.05 0.48 Q11 1 0.5205 0.7764 0.3326 11.00000 0.05 0.47 Q12 1 0.6963 0.6500 0.1371 11.00000 0.05 0.46 Q13 1 0.6387 0.6001 0.2210 11.00000 0.05 0.46 Q14 1 0.7533 0.5840 0.1094 11.00000 0.05 0.43 Q15 1 0.6779 0.6024 0.1387 11.00000 0.05 0.43 Q16 1 0.6324 0.7333 0.7214 11.00000 0.05 0.43 Q17 1 0.5334 0.7173 0.4269 11.00000 0.05 0.42 Q18 1 0.4898 0.7450 0.4165 11.00000 0.05 0.41 Q19 1 0.5598 0.7217 0.8174 11.00000 0.05 0.40 Q20 1 0.5278 0.6849 0.5159 11.00000 0.05 0.40 ; _shelx_res_checksum 50289 _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 1.945 _oxdiff_exptl_absorpt_empirical_full_min 0.469 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 0.78925(2) 0.63518(2) 0.12142(2) 0.02886(9) Uani 1 1 d . . . . . O1 O 0.7216(2) 0.48742(13) 0.31772(19) 0.0279(5) Uani 1 1 d . . . . . O2 O 0.6131(3) 0.42058(16) 0.1419(2) 0.0452(7) Uani 1 1 d . . . . . O3 O 0.4659(2) 0.58936(12) 0.26954(18) 0.0213(4) Uani 1 1 d . . . . . O4 O 0.3602(2) 0.56393(15) 0.4036(2) 0.0311(5) Uani 1 1 d . . . . . C1 C 0.7681(4) 0.4007(2) 0.3704(3) 0.0322(7) Uani 1 1 d . . . . . H1A H 0.824456 0.374652 0.327750 0.048 Uiso 1 1 calc GR . . . . H1B H 0.693442 0.362160 0.363335 0.048 Uiso 1 1 calc GR . . . . H1C H 0.817038 0.408050 0.454828 0.048 Uiso 1 1 calc GR . . . . C2 C 0.6471(3) 0.48693(19) 0.2021(3) 0.0244(6) Uani 1 1 d . . . . . C3 C 0.6119(3) 0.5796(2) 0.1513(3) 0.0248(6) Uani 1 1 d . . . . . H3 H 0.541544 0.575736 0.073333 0.030 Uiso 1 1 calc R . . . . C4 C 0.5680(3) 0.64169(17) 0.2367(3) 0.0202(6) Uani 1 1 d . . . . . H4 H 0.642639 0.653318 0.309721 0.024 Uiso 1 1 calc R . . . . C5 C 0.5056(3) 0.72903(18) 0.1831(3) 0.0193(6) Uani 1 1 d . . . . . C6 C 0.4628(3) 0.7465(2) 0.0595(3) 0.0251(6) Uani 1 1 d . . . . . H6 H 0.476614 0.704513 0.004829 0.030 Uiso 1 1 calc R . . . . C7 C 0.3990(3) 0.8268(2) 0.0167(3) 0.0258(6) Uani 1 1 d . . . . . H7 H 0.371527 0.839156 -0.066375 0.031 Uiso 1 1 calc R . . . . C8 C 0.3767(3) 0.8880(2) 0.0984(3) 0.0261(6) Uani 1 1 d . . . . . H8 H 0.332812 0.941209 0.069033 0.031 Uiso 1 1 calc R . . . . C9 C 0.4181(3) 0.87243(18) 0.2235(3) 0.0214(6) Uani 1 1 d . . . . . C10 C 0.3853(3) 0.9426(2) 0.3052(3) 0.0299(7) Uani 1 1 d . . . . . H10A H 0.375911 0.914408 0.377225 0.045 Uiso 1 1 calc GR . . . . H10B H 0.303677 0.971845 0.262344 0.045 Uiso 1 1 calc GR . . . . H10C H 0.455383 0.986065 0.327808 0.045 Uiso 1 1 calc GR . . . . C11 C 0.4849(3) 0.79183(17) 0.2669(2) 0.0172(5) Uani 1 1 d . . . . . C12 C 0.5328(3) 0.77108(18) 0.3996(3) 0.0178(5) Uani 1 1 d . . . . . C13 C 0.6020(3) 0.83480(19) 0.4827(3) 0.0216(6) Uani 1 1 d . . . . . H13 H 0.624535 0.888663 0.453339 0.026 Uiso 1 1 calc R . . . . C14 C 0.6387(3) 0.82115(19) 0.6072(3) 0.0246(6) Uani 1 1 d . . . . . H14 H 0.685688 0.865329 0.659594 0.030 Uiso 1 1 calc R . . . . C15 C 0.6056(3) 0.7412(2) 0.6552(3) 0.0237(6) Uani 1 1 d . . . . . C16 C 0.6373(3) 0.7284(2) 0.7906(3) 0.0329(7) Uani 1 1 d . . . . . H16A H 0.731399 0.732912 0.827981 0.049 Uiso 1 1 calc GR . . . . H16B H 0.607466 0.670263 0.806926 0.049 Uiso 1 1 calc GR . . . . H16C H 0.593250 0.773661 0.823457 0.049 Uiso 1 1 calc GR . . . . C17 C 0.5428(3) 0.6750(2) 0.5743(3) 0.0215(6) Uani 1 1 d . . . . . H17 H 0.523862 0.620451 0.604433 0.026 Uiso 1 1 calc R . . . . C18 C 0.5070(3) 0.68842(18) 0.4480(3) 0.0179(5) Uani 1 1 d . . . . . C19 C 0.4380(3) 0.61067(19) 0.3739(3) 0.0200(6) Uani 1 1 d . . . . . 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 0.02869(13) 0.03432(14) 0.02627(13) 0.00398(7) 0.01236(9) 0.00315(8) O1 0.0342(12) 0.0210(10) 0.0270(11) -0.0006(8) 0.0071(10) 0.0061(9) O2 0.0608(17) 0.0270(13) 0.0397(15) -0.0113(10) 0.0028(13) -0.0021(12) O3 0.0231(10) 0.0177(9) 0.0239(10) -0.0035(7) 0.0083(8) -0.0033(8) O4 0.0331(12) 0.0330(12) 0.0309(12) -0.0043(9) 0.0151(10) -0.0140(10) C1 0.0378(19) 0.0279(16) 0.0332(18) 0.0076(13) 0.0140(15) 0.0131(15) C2 0.0224(14) 0.0258(15) 0.0271(16) -0.0025(11) 0.0105(12) 0.0023(12) C3 0.0254(15) 0.0263(15) 0.0200(14) -0.0050(10) 0.0026(12) -0.0001(12) C4 0.0199(14) 0.0214(14) 0.0185(14) -0.0029(10) 0.0044(11) -0.0010(11) C5 0.0166(13) 0.0206(14) 0.0201(14) -0.0011(10) 0.0046(11) -0.0012(11) C6 0.0231(14) 0.0299(16) 0.0211(15) -0.0034(11) 0.0051(12) -0.0018(12) C7 0.0223(14) 0.0344(16) 0.0164(14) 0.0042(11) -0.0005(12) -0.0012(13) C8 0.0237(15) 0.0266(15) 0.0254(16) 0.0089(11) 0.0036(13) 0.0033(12) C9 0.0184(13) 0.0204(14) 0.0259(16) 0.0017(10) 0.0072(12) 0.0004(11) C10 0.0340(17) 0.0199(14) 0.0343(18) 0.0019(12) 0.0080(14) 0.0094(13) C11 0.0149(12) 0.0179(13) 0.0183(13) 0.0016(9) 0.0041(10) -0.0008(10) C12 0.0144(12) 0.0180(13) 0.0212(13) -0.0012(10) 0.0054(11) 0.0023(10) C13 0.0211(14) 0.0174(13) 0.0250(15) -0.0008(10) 0.0046(12) 0.0010(11) C14 0.0249(15) 0.0231(15) 0.0226(15) -0.0067(11) 0.0023(12) -0.0014(12) C15 0.0185(14) 0.0330(16) 0.0190(14) 0.0007(11) 0.0047(11) 0.0050(12) C16 0.0306(17) 0.048(2) 0.0189(15) -0.0007(13) 0.0051(13) 0.0040(15) C17 0.0161(13) 0.0256(15) 0.0227(14) 0.0036(11) 0.0057(11) 0.0033(11) C18 0.0137(12) 0.0184(13) 0.0213(14) -0.0007(10) 0.0049(11) 0.0008(10) C19 0.0190(13) 0.0202(13) 0.0203(14) 0.0017(10) 0.0051(11) -0.0008(11) 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' I I -0.4742 1.8119 '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' 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 116.0(2) . . ? C19 O3 C4 118.3(2) . . ? O1 C2 C3 112.8(2) . . ? O2 C2 O1 124.6(3) . . ? O2 C2 C3 122.6(3) . . ? C2 C3 I1 106.7(2) . . ? C2 C3 C4 113.4(3) . . ? C4 C3 I1 108.35(19) . . ? O3 C4 C3 103.4(2) . . ? O3 C4 C5 107.5(2) . . ? C5 C4 C3 116.4(2) . . ? C6 C5 C4 123.6(3) . . ? C6 C5 C11 120.5(3) . . ? C11 C5 C4 115.8(2) . . ? C5 C6 C7 120.1(3) . . ? C8 C7 C6 119.6(3) . . ? C7 C8 C9 121.8(3) . . ? C8 C9 C10 117.7(3) . . ? C8 C9 C11 118.5(3) . . ? C11 C9 C10 123.7(3) . . ? C5 C11 C9 119.4(3) . . ? C5 C11 C12 119.2(2) . . ? C9 C11 C12 121.4(2) . . ? C13 C12 C11 120.6(2) . . ? C13 C12 C18 116.8(3) . . ? C18 C12 C11 122.6(2) . . ? C14 C13 C12 122.5(3) . . ? C13 C14 C15 120.5(3) . . ? C14 C15 C16 120.8(3) . . ? C17 C15 C14 118.0(3) . . ? C17 C15 C16 121.2(3) . . ? C15 C17 C18 121.4(3) . . ? C12 C18 C19 124.9(2) . . ? C17 C18 C12 120.6(3) . . ? C17 C18 C19 114.5(2) . . ? O3 C19 C18 119.2(2) . . ? O4 C19 O3 117.6(3) . . ? O4 C19 C18 123.2(3) . . ? 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 2.169(3) . ? O1 C1 1.450(4) . ? O1 C2 1.326(4) . ? O2 C2 1.200(4) . ? O3 C4 1.470(4) . ? O3 C19 1.356(4) . ? O4 C19 1.202(4) . ? C2 C3 1.505(4) . ? C3 C4 1.520(4) . ? C4 C5 1.507(4) . ? C5 C6 1.380(4) . ? C5 C11 1.407(4) . ? C6 C7 1.391(4) . ? C7 C8 1.380(5) . ? C8 C9 1.392(4) . ? C9 C10 1.515(4) . ? C9 C11 1.408(4) . ? C11 C12 1.489(4) . ? C12 C13 1.391(4) . ? C12 C18 1.413(4) . ? C13 C14 1.381(4) . ? C14 C15 1.402(4) . ? C15 C16 1.504(4) . ? C15 C17 1.383(4) . ? C17 C18 1.401(4) . ? C18 C19 1.494(4) . ?