#------------------------------------------------------------------------------ #$Date: 2020-07-06 05:03:52 +0300 (Mon, 06 Jul 2020) $ #$Revision: 253819 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/64/7126468.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_7126468 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 H17 I O5' _chemical_formula_sum 'C19 H17 I O5' _chemical_formula_weight 452.22 _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 2019-06-14 _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 111.642(2) _cell_angle_beta 106.312(2) _cell_angle_gamma 106.245(2) _cell_formula_units_Z 2 _cell_length_a 9.8357(2) _cell_length_b 10.4353(3) _cell_length_c 10.4634(3) _cell_measurement_reflns_used 8993 _cell_measurement_temperature 99.98(10) _cell_measurement_theta_max 30.0630 _cell_measurement_theta_min 2.3080 _cell_volume 865.10(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_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 0.842 _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 -3.00 31.00 0.50 0.53 -- 10.30 -57.00 -30.00 68 2 \w -5.00 21.00 0.50 0.53 -- 10.30 -99.00 -30.00 52 3 \w -14.00 30.00 0.50 0.53 -- -9.20 -99.00 -90.00 88 4 \w 22.00 48.00 0.50 0.53 -- 10.30-104.00-179.00 52 5 \w -17.00 9.00 0.50 0.53 -- -9.20 -99.00 -30.00 52 6 \w -26.00 6.00 0.50 0.53 -- -9.20 -99.00 60.00 64 7 \w -25.00 48.00 0.50 0.53 -- 10.30 -99.00 120.00 146 8 \w -64.00 -31.00 0.50 0.53 -- 10.30 -57.00 -30.00 66 9 \w -3.00 22.00 0.50 0.53 -- -9.20 -19.00 -30.00 50 10 \w 38.00 64.00 0.50 0.53 -- -9.20 57.00-180.00 52 11 \w -23.00 10.00 0.50 0.53 -- -9.20 57.00-180.00 66 12 \w -85.00 -39.00 0.50 0.53 -- -9.20 -19.00 -30.00 92 13 \w -60.00 -25.00 0.50 0.53 -- 10.30 -57.00 0.00 70 14 \w -64.00 29.00 0.50 0.53 -- 10.30 -57.00-120.00 186 ; _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 -0.0108288000 _diffrn_orient_matrix_UB_12 -0.0768852000 _diffrn_orient_matrix_UB_13 -0.0268588000 _diffrn_orient_matrix_UB_21 0.0352445000 _diffrn_orient_matrix_UB_22 0.0148909000 _diffrn_orient_matrix_UB_23 0.0761901000 _diffrn_orient_matrix_UB_31 -0.0745981000 _diffrn_orient_matrix_UB_32 -0.0206194000 _diffrn_orient_matrix_UB_33 0.0011126000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0539 _diffrn_reflns_av_unetI/netI 0.0500 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.842 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 13105 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.842 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 30.126 _diffrn_reflns_theta_min 2.320 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 1.878 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.17551 _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 1.736 _exptl_crystal_description block _exptl_crystal_F_000 448 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.876 _refine_diff_density_min -1.700 _refine_diff_density_rms 0.172 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 227 _refine_ls_number_reflns 4297 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.024 _refine_ls_R_factor_all 0.0362 _refine_ls_R_factor_gt 0.0317 _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^)+(0.0425P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0743 _refine_ls_wR_factor_ref 0.0762 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3978 _reflns_number_total 4297 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9cc10080f2.cif _cod_data_source_block tpt-9-7 _cod_depositor_comments 'Adding full bibliography for 7126465--7126470.cif.' _cod_original_cell_volume 865.10(4) _cod_database_code 7126468 _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 0.705 _shelx_estimated_absorpt_t_min 0.705 _reflns_odcompleteness_completeness 99.86 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _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 Ternary CH refined with riding coordinates: C6(H6), C7(H7) 2.b Secondary CH2 refined with riding coordinates: C1(H1A,H1B), C4(H4A,H4B) 2.c Aromatic/amide H refined with riding coordinates: C9(H9), C10(H10), C11(H11), C12(H12), C15(H15), C16(H16), C17(H17), C18(H18) 2.d Idealised Me refined as rotating group: C2(H2A,H2B,H2C) ; _shelx_res_file ; TITL tpt-9-7_a.res in P-1 tpt-9-7.res created by SHELXL-2018/3 at 18:15:24 on 14-Jun-2019 REM Old TITL tpt-9-7 in P1 REM SHELXT solution in P-1: R1 0.097, Rweak 0.013, Alpha 0.044 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C19 N O5 I CELL 0.71073 9.8357 10.4353 10.4634 111.642 106.312 106.245 ZERR 2 0.0002 0.0003 0.0003 0.002 0.002 0.002 LATT 1 SFAC C H I O UNIT 38 34 2 10 L.S. 4 0 0 PLAN 20 SIZE 0.2 0.2 0.2 list 4 fmap 2 53 ACTA OMIT 4 -8 6 REM REM REM WGHT 0.042500 FVAR 0.62909 I1 3 0.068829 0.980403 0.699951 11.00000 0.02761 0.01748 = 0.02256 0.01038 0.01394 0.01385 O1 4 0.639971 0.902699 0.894712 11.00000 0.03205 0.03685 = 0.04567 0.02410 0.02374 0.02338 O2 4 0.310998 0.801373 0.797321 11.00000 0.02026 0.02476 = 0.01921 0.01375 0.00800 0.01122 O3 4 0.105503 0.720098 0.848672 11.00000 0.03339 0.03797 = 0.02698 0.02355 0.01796 0.01496 O4 4 0.150485 0.587909 0.488640 11.00000 0.01945 0.01630 = 0.02090 0.01125 0.01189 0.01091 O5 4 0.292850 0.465670 0.436698 11.00000 0.02624 0.02421 = 0.03937 0.02000 0.01796 0.01727 C1 1 0.543723 0.770119 0.887633 11.00000 0.02959 0.02460 = 0.02782 0.01059 0.00781 0.01633 AFIX 23 H1A 2 0.604464 0.748494 0.960871 11.00000 -1.20000 H1B 2 0.501892 0.683928 0.786772 11.00000 -1.20000 AFIX 0 C2 1 0.767130 0.887773 0.860140 11.00000 0.03269 0.05686 = 0.03487 0.02194 0.02017 0.02968 AFIX 137 H2A 2 0.726884 0.813201 0.755170 11.00000 -1.50000 H2B 2 0.823197 0.855725 0.923861 11.00000 -1.50000 H2C 2 0.836757 0.984364 0.878158 11.00000 -1.50000 AFIX 0 C3 1 0.258817 0.568550 0.436428 11.00000 0.01579 0.01871 = 0.01866 0.00831 0.00673 0.00918 C4 1 0.412326 0.793378 0.922239 11.00000 0.02905 0.02080 = 0.01974 0.01233 0.00640 0.01102 AFIX 23 H4A 2 0.353821 0.709210 0.932926 11.00000 -1.20000 H4B 2 0.453436 0.887230 1.016830 11.00000 -1.20000 AFIX 0 C5 1 0.160608 0.757482 0.772337 11.00000 0.02294 0.01474 = 0.01754 0.00857 0.01025 0.00963 C6 1 0.062965 0.756151 0.630817 11.00000 0.01826 0.01227 = 0.01776 0.00918 0.01008 0.00752 AFIX 13 H6 2 -0.045543 0.680666 0.587805 11.00000 -1.20000 AFIX 0 C7 1 0.122780 0.722812 0.508549 11.00000 0.01759 0.01239 = 0.01629 0.00837 0.00854 0.00851 AFIX 13 H7 2 0.222762 0.809003 0.545536 11.00000 -1.20000 AFIX 0 C8 1 0.014841 0.688301 0.353764 11.00000 0.02081 0.01186 = 0.01546 0.00654 0.00740 0.00783 C9 1 -0.144844 0.647126 0.306264 11.00000 0.02189 0.01890 = 0.01984 0.00817 0.00928 0.01118 AFIX 43 H9 2 -0.189799 0.644584 0.373031 11.00000 -1.20000 AFIX 0 C10 1 -0.238050 0.609470 0.157901 11.00000 0.02034 0.02283 = 0.02420 0.00987 0.00406 0.01155 AFIX 43 H10 2 -0.345275 0.580918 0.125571 11.00000 -1.20000 AFIX 0 C11 1 -0.170726 0.614686 0.059141 11.00000 0.03000 0.02357 = 0.01523 0.00844 0.00273 0.01564 AFIX 43 H11 2 -0.232909 0.590231 -0.039291 11.00000 -1.20000 AFIX 0 C12 1 -0.011418 0.656073 0.105936 11.00000 0.03147 0.02208 = 0.01996 0.01130 0.01459 0.01709 AFIX 43 H12 2 0.033183 0.660646 0.039335 11.00000 -1.20000 AFIX 0 C13 1 0.082338 0.690906 0.252512 11.00000 0.02097 0.01348 = 0.01803 0.00847 0.00922 0.00929 C14 1 0.253833 0.731044 0.301967 11.00000 0.02342 0.01759 = 0.01667 0.00856 0.00998 0.01010 C15 1 0.339215 0.825062 0.258890 11.00000 0.03035 0.02420 = 0.02159 0.01430 0.01428 0.01186 AFIX 43 H15 2 0.288293 0.860358 0.199888 11.00000 -1.20000 AFIX 0 C16 1 0.498277 0.866767 0.302337 11.00000 0.02737 0.02955 = 0.02494 0.01464 0.01529 0.00634 AFIX 43 H16 2 0.553685 0.932397 0.275431 11.00000 -1.20000 AFIX 0 C17 1 0.575598 0.810890 0.386102 11.00000 0.02127 0.03196 = 0.02732 0.01257 0.01347 0.01065 AFIX 43 H17 2 0.682549 0.839377 0.415737 11.00000 -1.20000 AFIX 0 C18 1 0.492662 0.713272 0.424692 11.00000 0.02320 0.02820 = 0.02493 0.01466 0.01321 0.01520 AFIX 43 H18 2 0.543188 0.672114 0.476481 11.00000 -1.20000 AFIX 0 C19 1 0.333374 0.674938 0.387199 11.00000 0.02097 0.01743 = 0.01736 0.00744 0.01078 0.00958 HKLF 4 REM tpt-9-7_a.res in P-1 REM wR2 = 0.0762, GooF = S = 1.024, Restrained GooF = 1.024 for all data REM R1 = 0.0317 for 3978 Fo > 4sig(Fo) and 0.0362 for all 4297 data REM 227 parameters refined using 0 restraints END WGHT 0.0425 0.0000 REM Highest difference peak 0.876, deepest hole -1.700, 1-sigma level 0.172 Q1 1 0.0677 0.9708 0.7882 11.00000 0.05 0.88 Q2 1 0.0804 0.9938 0.6170 11.00000 0.05 0.82 Q3 1 0.0021 0.8910 0.7059 11.00000 0.05 0.76 Q4 1 -0.0511 0.9549 0.7079 11.00000 0.05 0.74 Q5 1 0.2046 1.0003 0.6795 11.00000 0.05 0.69 Q6 1 0.1412 1.0747 0.6954 11.00000 0.05 0.62 Q7 1 0.9046 1.0968 0.8995 11.00000 0.05 0.61 Q8 1 0.8207 0.8994 0.6425 11.00000 0.05 0.56 Q9 1 0.1498 0.9325 0.7646 11.00000 0.05 0.55 Q10 1 0.8187 0.8163 0.5449 11.00000 0.05 0.55 Q11 1 0.1021 0.7588 0.7000 11.00000 0.05 0.55 Q12 1 -0.0229 0.7879 -0.0281 11.00000 0.05 0.53 Q13 1 0.2172 0.9835 0.7966 11.00000 0.05 0.53 Q14 1 0.7283 0.7936 1.1593 11.00000 0.05 0.53 Q15 1 -0.3096 0.4647 -0.1783 11.00000 0.05 0.52 Q16 1 0.1396 1.1567 0.7419 11.00000 0.05 0.52 Q17 1 -0.1239 0.6973 0.6826 11.00000 0.05 0.51 Q18 1 -0.2350 0.7390 0.4925 11.00000 0.05 0.50 Q19 1 0.4425 0.8986 0.7648 11.00000 0.05 0.50 Q20 1 0.3861 0.6360 1.0993 11.00000 0.05 0.50 ; _shelx_res_checksum 30636 _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 2.219 _oxdiff_exptl_absorpt_empirical_full_min 0.517 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 0.06883(2) 0.98040(2) 0.69995(2) 0.02044(7) Uani 1 1 d . . . . . O1 O 0.6400(2) 0.9027(2) 0.8947(3) 0.0328(5) Uani 1 1 d . . . . . O2 O 0.31100(18) 0.8014(2) 0.79732(19) 0.0201(4) Uani 1 1 d . . . . . O3 O 0.1055(2) 0.7201(2) 0.8487(2) 0.0289(4) Uani 1 1 d . . . . . O4 O 0.15049(18) 0.58791(18) 0.4886(2) 0.0165(3) Uani 1 1 d . . . . . O5 O 0.2929(2) 0.4657(2) 0.4367(2) 0.0257(4) Uani 1 1 d . . . . . C1 C 0.5437(3) 0.7701(3) 0.8876(3) 0.0281(6) Uani 1 1 d . . . . . H1A H 0.604464 0.748494 0.960871 0.034 Uiso 1 1 calc R . . . . H1B H 0.501892 0.683928 0.786772 0.034 Uiso 1 1 calc R . . . . C2 C 0.7671(3) 0.8878(4) 0.8601(4) 0.0375(7) Uani 1 1 d . . . . . H2A H 0.726884 0.813201 0.755170 0.056 Uiso 1 1 calc GR . . . . H2B H 0.823197 0.855725 0.923861 0.056 Uiso 1 1 calc GR . . . . H2C H 0.836757 0.984364 0.878158 0.056 Uiso 1 1 calc GR . . . . C3 C 0.2588(3) 0.5685(3) 0.4364(3) 0.0177(5) Uani 1 1 d . . . . . C4 C 0.4123(3) 0.7934(3) 0.9222(3) 0.0233(5) Uani 1 1 d . . . . . H4A H 0.353821 0.709210 0.932926 0.028 Uiso 1 1 calc R . . . . H4B H 0.453436 0.887230 1.016830 0.028 Uiso 1 1 calc R . . . . C5 C 0.1606(3) 0.7575(3) 0.7723(3) 0.0174(5) Uani 1 1 d . . . . . C6 C 0.0630(3) 0.7562(2) 0.6308(3) 0.0146(4) Uani 1 1 d . . . . . H6 H -0.045543 0.680666 0.587805 0.018 Uiso 1 1 calc R . . . . C7 C 0.1228(3) 0.7228(3) 0.5085(3) 0.0141(4) Uani 1 1 d . . . . . H7 H 0.222762 0.809003 0.545536 0.017 Uiso 1 1 calc R . . . . C8 C 0.0148(3) 0.6883(3) 0.3538(3) 0.0160(4) Uani 1 1 d . . . . . C9 C -0.1448(3) 0.6471(3) 0.3063(3) 0.0199(5) Uani 1 1 d . . . . . H9 H -0.189799 0.644584 0.373031 0.024 Uiso 1 1 calc R . . . . C10 C -0.2381(3) 0.6095(3) 0.1579(3) 0.0238(5) Uani 1 1 d . . . . . H10 H -0.345275 0.580918 0.125571 0.029 Uiso 1 1 calc R . . . . C11 C -0.1707(3) 0.6147(3) 0.0591(3) 0.0240(5) Uani 1 1 d . . . . . H11 H -0.232909 0.590231 -0.039291 0.029 Uiso 1 1 calc R . . . . C12 C -0.0114(3) 0.6561(3) 0.1059(3) 0.0218(5) Uani 1 1 d . . . . . H12 H 0.033183 0.660646 0.039335 0.026 Uiso 1 1 calc R . . . . C13 C 0.0823(3) 0.6909(3) 0.2525(3) 0.0165(5) Uani 1 1 d . . . . . C14 C 0.2538(3) 0.7310(3) 0.3020(3) 0.0185(5) Uani 1 1 d . . . . . C15 C 0.3392(3) 0.8251(3) 0.2589(3) 0.0234(5) Uani 1 1 d . . . . . H15 H 0.288293 0.860358 0.199888 0.028 Uiso 1 1 calc R . . . . C16 C 0.4983(3) 0.8668(3) 0.3023(3) 0.0273(6) Uani 1 1 d . . . . . H16 H 0.553685 0.932397 0.275431 0.033 Uiso 1 1 calc R . . . . C17 C 0.5756(3) 0.8109(3) 0.3861(3) 0.0269(6) Uani 1 1 d . . . . . H17 H 0.682549 0.839377 0.415737 0.032 Uiso 1 1 calc R . . . . C18 C 0.4927(3) 0.7133(3) 0.4247(3) 0.0230(5) Uani 1 1 d . . . . . H18 H 0.543188 0.672114 0.476481 0.028 Uiso 1 1 calc R . . . . C19 C 0.3334(3) 0.6749(3) 0.3872(3) 0.0179(5) 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 0.02761(11) 0.01748(10) 0.02256(11) 0.01038(8) 0.01394(8) 0.01385(7) O1 0.0321(10) 0.0369(11) 0.0457(13) 0.0241(10) 0.0237(9) 0.0234(9) O2 0.0203(8) 0.0248(9) 0.0192(9) 0.0137(8) 0.0080(7) 0.0112(7) O3 0.0334(10) 0.0380(11) 0.0270(10) 0.0236(9) 0.0180(9) 0.0150(9) O4 0.0195(8) 0.0163(8) 0.0209(8) 0.0113(7) 0.0119(7) 0.0109(6) O5 0.0262(9) 0.0242(9) 0.0394(11) 0.0200(9) 0.0180(8) 0.0173(7) C1 0.0296(13) 0.0246(13) 0.0278(14) 0.0106(12) 0.0078(11) 0.0163(11) C2 0.0327(15) 0.057(2) 0.0349(17) 0.0219(15) 0.0202(13) 0.0297(14) C3 0.0158(10) 0.0187(11) 0.0187(11) 0.0083(10) 0.0067(9) 0.0092(9) C4 0.0290(13) 0.0208(12) 0.0197(12) 0.0123(11) 0.0064(10) 0.0110(10) C5 0.0229(11) 0.0147(11) 0.0175(11) 0.0086(9) 0.0102(9) 0.0096(9) C6 0.0183(10) 0.0123(10) 0.0178(11) 0.0092(9) 0.0101(9) 0.0075(8) C7 0.0176(10) 0.0124(10) 0.0163(11) 0.0084(9) 0.0085(9) 0.0085(8) C8 0.0208(11) 0.0119(10) 0.0155(11) 0.0065(9) 0.0074(9) 0.0078(9) C9 0.0219(11) 0.0189(11) 0.0198(12) 0.0082(10) 0.0093(10) 0.0112(9) C10 0.0203(12) 0.0228(12) 0.0242(13) 0.0099(11) 0.0041(10) 0.0116(10) C11 0.0300(13) 0.0236(13) 0.0152(12) 0.0084(10) 0.0027(10) 0.0156(10) C12 0.0315(13) 0.0221(12) 0.0200(12) 0.0113(10) 0.0146(11) 0.0171(11) C13 0.0210(11) 0.0135(10) 0.0180(11) 0.0085(9) 0.0092(9) 0.0093(9) C14 0.0234(11) 0.0176(11) 0.0167(11) 0.0086(10) 0.0100(9) 0.0101(9) C15 0.0303(13) 0.0242(13) 0.0216(12) 0.0143(11) 0.0143(10) 0.0119(10) C16 0.0274(13) 0.0295(14) 0.0249(14) 0.0146(12) 0.0153(11) 0.0063(11) C17 0.0213(12) 0.0320(15) 0.0273(14) 0.0126(12) 0.0135(11) 0.0107(11) C18 0.0232(12) 0.0282(13) 0.0249(13) 0.0147(11) 0.0132(10) 0.0152(10) C19 0.0210(11) 0.0174(11) 0.0174(11) 0.0074(10) 0.0108(9) 0.0096(9) 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 C1 O1 C2 112.2(2) . . ? C5 O2 C4 116.23(19) . . ? C3 O4 C7 117.97(18) . . ? O1 C1 C4 109.1(2) . . ? O4 C3 C19 119.7(2) . . ? O5 C3 O4 117.0(2) . . ? O5 C3 C19 123.3(2) . . ? O2 C4 C1 107.9(2) . . ? O2 C5 C6 111.7(2) . . ? O3 C5 O2 125.5(2) . . ? O3 C5 C6 122.7(2) . . ? C5 C6 I1 107.28(14) . . ? C5 C6 C7 114.25(19) . . ? C7 C6 I1 107.51(14) . . ? O4 C7 C6 106.12(17) . . ? O4 C7 C8 106.99(18) . . ? C8 C7 C6 116.91(18) . . ? C9 C8 C7 123.6(2) . . ? C9 C8 C13 120.0(2) . . ? C13 C8 C7 116.33(19) . . ? C8 C9 C10 119.9(2) . . ? C11 C10 C9 120.0(2) . . ? C10 C11 C12 120.4(2) . . ? C11 C12 C13 120.2(2) . . ? C8 C13 C14 120.2(2) . . ? C12 C13 C8 119.5(2) . . ? C12 C13 C14 120.4(2) . . ? C15 C14 C13 118.8(2) . . ? C15 C14 C19 118.0(2) . . ? C19 C14 C13 123.2(2) . . ? C16 C15 C14 121.3(2) . . ? C15 C16 C17 120.3(2) . . ? C18 C17 C16 119.5(2) . . ? C17 C18 C19 121.0(2) . . ? C14 C19 C3 125.0(2) . . ? C18 C19 C3 115.1(2) . . ? C18 C19 C14 119.9(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 I1 C6 2.158(2) . ? O1 C1 1.403(3) . ? O1 C2 1.429(3) . ? O2 C4 1.450(3) . ? O2 C5 1.335(3) . ? O3 C5 1.199(3) . ? O4 C3 1.357(3) . ? O4 C7 1.459(3) . ? O5 C3 1.211(3) . ? C1 C4 1.495(4) . ? C3 C19 1.488(3) . ? C5 C6 1.515(3) . ? C6 C7 1.521(3) . ? C7 C8 1.507(3) . ? C8 C9 1.387(3) . ? C8 C13 1.404(3) . ? C9 C10 1.398(3) . ? C10 C11 1.384(4) . ? C11 C12 1.384(4) . ? C12 C13 1.393(3) . ? C13 C14 1.498(3) . ? C14 C15 1.396(3) . ? C14 C19 1.414(3) . ? C15 C16 1.385(4) . ? C16 C17 1.392(4) . ? C17 C18 1.375(4) . ? C18 C19 1.399(3) . ?