#------------------------------------------------------------------------------ #$Date: 2021-06-30 04:02:58 +0300 (Wed, 30 Jun 2021) $ #$Revision: 266794 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/85/7128564.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_7128564 loop_ _publ_author_name 'Du, Yunfei' 'Zhang, Jingran' 'Jalil, Ayesha' 'He, Jiaxin' 'Yu, Zhenyang' 'Cheng, Yifu' 'Li, Guangchen' 'Zhao, Kang' _publ_section_title ; Lactonization with concomitant 1,2-aryl migration and alkoxylation mediated by dialkoxyphenyl iodides generated in situ ; _journal_name_full 'Chemical Communications' _journal_paper_doi 10.1039/D1CC03110D _journal_year 2021 _chemical_formula_moiety 'C16 H14 O3' _chemical_formula_sum 'C16 H14 O3' _chemical_formula_weight 254.27 _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2020-05-21 _audit_creation_method ; Olex2 1.3-alpha (compiled 2020.05.07 svn.rd67b107b for OlexSys, GUI svn.r6105) ; _audit_update_record ; 2021-02-19 deposited with the CCDC. 2021-06-28 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 93.2470(10) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 16.74290(10) _cell_length_b 10.55120(10) _cell_length_c 14.69710(10) _cell_measurement_reflns_used 28149 _cell_measurement_temperature 99.97(11) _cell_measurement_theta_max 72.6730 _cell_measurement_theta_min 4.9180 _cell_volume 2592.19(3) _computing_cell_refinement 'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)' _computing_data_collection 'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)' _computing_data_reduction 'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)' _computing_molecular_graphics 'Olex2 1.3-alpha (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3-alpha (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 99.97(11) _diffrn_detector 'CCD plate' _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.984 _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 -113.00 -32.00 0.50 0.05 -- -35.99 149.00-165.00 162 2 \w -111.00 -64.00 0.50 0.05 -- -35.99-149.00 147.00 94 3 \w -98.00 -19.00 0.50 0.05 -- -35.99 123.00 31.00 158 4 \w 58.00 111.00 0.50 0.05 -- 35.99 149.00-165.00 106 5 \w 13.00 98.00 0.50 0.05 -- 35.99-123.00 -49.00 170 6 \w 26.00 113.00 0.50 0.05 -- 35.99-149.00 147.00 174 7 \w -171.00 -63.00 0.50 0.20 -- -100.00-149.00 147.00 216 8 \w -177.00 -80.00 0.50 0.20 -- -100.00-123.00 -49.00 194 9 \w -134.00 -32.00 0.50 0.20 -- -100.00 149.00-165.00 204 10 \w -115.00 -19.00 0.50 0.20 -- -100.00 123.00 31.00 192 11 \w 75.00 178.00 0.50 0.20 -- 108.37 123.00 31.00 206 12 \w 28.00 115.00 0.50 0.20 -- 108.37-123.00 -49.00 174 13 \w 33.00 133.00 0.50 0.20 -- 108.37-149.00 147.00 200 14 \w 6.00 113.00 0.50 0.05 -- 35.99 57.00-180.00 214 15 \w 6.00 113.00 0.50 0.05 -- 35.99 57.00 0.00 214 16 \w -48.00 75.00 0.50 0.05 -- 35.99 -37.00-180.00 246 17 \w 6.00 113.00 0.50 0.05 -- 35.99 57.00 120.00 214 18 \w -177.00 -86.00 0.50 0.20 -- -100.00-111.00-150.00 182 19 \w -177.00 -84.00 0.50 0.20 -- -100.00 -94.00-120.00 186 20 \w -111.00 -17.00 0.50 0.20 -- -100.00 111.00-150.00 188 21 \w -177.00 -84.00 0.50 0.20 -- -100.00 -94.00-180.00 186 22 \w -132.00 -24.00 0.50 0.20 -- -100.00 61.00-120.00 216 23 \w -177.00 -84.00 0.50 0.20 -- -100.00 -94.00 60.00 186 24 \w 81.00 178.00 0.50 0.20 -- 108.37 111.00 -30.00 194 25 \w 77.00 178.00 0.50 0.20 -- 108.37 61.00 -60.00 202 26 \w 74.00 178.00 0.50 0.20 -- 108.37 45.00-120.00 208 27 \w 81.00 178.00 0.50 0.20 -- 108.37 111.00-180.00 194 28 \w 23.00 108.00 0.50 0.20 -- 108.37 -94.00 30.00 170 29 \w 26.00 112.00 0.50 0.20 -- 108.37-111.00 150.00 172 30 \w 23.00 108.00 0.50 0.20 -- 108.37 -94.00 60.00 170 31 \w 23.00 108.00 0.50 0.20 -- 108.37 -94.00 150.00 170 32 \w 23.00 108.00 0.50 0.20 -- 108.37 -94.00 -90.00 170 33 \w 27.00 143.00 0.50 0.20 -- 108.37 -45.00 -90.00 232 34 \w -115.00 2.00 0.50 0.05 -- -35.99 -77.00 -30.00 234 35 \w 39.00 124.00 0.50 0.05 -- 35.99 179.00 90.00 170 36 \w 6.00 113.00 0.50 0.05 -- 35.99 57.00 30.00 214 37 \w -2.00 115.00 0.50 0.05 -- 35.99 77.00-150.00 234 38 \w -2.00 115.00 0.50 0.05 -- 35.99 77.00 -60.00 234 39 \w -2.00 115.00 0.50 0.05 -- 35.99 77.00 150.00 234 40 \w -2.00 115.00 0.50 0.05 -- 35.99 77.00 30.00 234 41 \w 6.00 113.00 0.50 0.05 -- 35.99 57.00 -90.00 214 42 \w -177.00 -62.00 0.50 0.20 -- -100.00 -77.00-150.00 230 43 \w -176.00 -68.00 0.50 0.20 -- -100.00 -61.00-150.00 216 44 \w -176.00 -68.00 0.50 0.20 -- -100.00 -61.00 0.00 216 45 \w -177.00 -62.00 0.50 0.20 -- -100.00 -77.00 -90.00 230 46 \w -176.00 -68.00 0.50 0.20 -- -100.00 -61.00-120.00 216 47 \w -177.00 -62.00 0.50 0.20 -- -100.00 -77.00 -30.00 230 48 \w -177.00 -62.00 0.50 0.20 -- -100.00 -77.00 60.00 230 49 \w -177.00 -65.00 0.50 0.20 -- -100.00 -45.00 150.00 224 50 \w -177.00 -62.00 0.50 0.20 -- -100.00 -77.00-120.00 230 51 \w -177.00 -62.00 0.50 0.20 -- -100.00 -77.00 0.00 230 52 \w -177.00 -62.00 0.50 0.20 -- -100.00 -77.00 -60.00 230 53 \w -177.00 -62.00 0.50 0.20 -- -100.00 -77.00 120.00 230 54 \w -177.00 -62.00 0.50 0.20 -- -100.00 -77.00-180.00 230 55 \w -176.00 -68.00 0.50 0.20 -- -100.00 -61.00 -30.00 216 56 \w -177.00 -62.00 0.50 0.20 -- -100.00 -77.00 30.00 230 57 \w -177.00 -51.00 0.50 0.20 -- -100.00 -30.00 60.00 252 58 \w -176.00 -68.00 0.50 0.20 -- -100.00 -61.00 -60.00 216 59 \w -176.00 -68.00 0.50 0.20 -- -100.00 -61.00 30.00 216 60 \w -177.00 -62.00 0.50 0.20 -- -100.00 -77.00 90.00 230 61 \w -176.00 -68.00 0.50 0.20 -- -100.00 -61.00 90.00 216 62 \w -176.00 -68.00 0.50 0.20 -- -100.00 -61.00 150.00 216 63 \w -176.00 -68.00 0.50 0.20 -- -100.00 -61.00 60.00 216 64 \w -177.00 -62.00 0.50 0.20 -- -100.00 -77.00 150.00 230 65 \w 70.00 178.00 0.50 0.20 -- 108.37 77.00 120.00 216 66 \w -125.00 -45.00 0.50 0.05 -- -35.99-179.00-150.00 160 67 \w -125.00 -45.00 0.50 0.05 -- -35.99-179.00 0.00 160 68 \w 6.00 113.00 0.50 0.05 -- 35.99 57.00 90.00 214 69 \w -3.00 120.00 0.50 0.05 -- 35.99 37.00 -30.00 246 70 \w 6.00 113.00 0.50 0.05 -- 35.99 57.00-150.00 214 71 \w -2.00 115.00 0.50 0.05 -- 35.99 77.00 -30.00 234 72 \w -3.00 120.00 0.50 0.05 -- 35.99 37.00 -90.00 246 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'ROD, Synergy Custom system, HyPix' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0133314000 _diffrn_orient_matrix_UB_12 0.1437250000 _diffrn_orient_matrix_UB_13 0.0098106000 _diffrn_orient_matrix_UB_21 -0.0907009000 _diffrn_orient_matrix_UB_22 -0.0224316000 _diffrn_orient_matrix_UB_23 0.0033478000 _diffrn_orient_matrix_UB_31 0.0095053000 _diffrn_orient_matrix_UB_32 -0.0127261000 _diffrn_orient_matrix_UB_33 0.1044669000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0393 _diffrn_reflns_av_unetI/netI 0.0105 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.984 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 45394 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.984 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 72.903 _diffrn_reflns_theta_min 4.957 _diffrn_source 'Rotating-anode X-ray tube' _diffrn_source_type 'Rigaku (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.728 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.94544 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.45g (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.303 _exptl_crystal_description block _exptl_crystal_F_000 1072 _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.06 _refine_diff_density_max 0.209 _refine_diff_density_min -0.291 _refine_diff_density_rms 0.049 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 173 _refine_ls_number_reflns 2550 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.088 _refine_ls_R_factor_all 0.0350 _refine_ls_R_factor_gt 0.0341 _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^)+(0.0403P)^2^+1.9252P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0848 _refine_ls_wR_factor_ref 0.0855 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2455 _reflns_number_total 2550 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1cc03110d2.cif _cod_data_source_block 034360_jiali3_100k_b _cod_database_code 7128564 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_usercomment 'Ian ' _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 0.958 _shelx_estimated_absorpt_t_min 0.899 _reflns_odcompleteness_completeness 100.00 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.49 _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 Secondary CH2 refined with riding coordinates: C7(H7a,H7b) 2.b Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C13(H13), C14(H14), C15(H15), C16(H16) 2.c Idealised Me refined as rotating group: C9(H9a,H9b,H9c) ; _shelx_res_file ; TITL 034360_jiali3_100k_b_a.res in C2/c 034360_jiali3_100k_b.res created by SHELXL-2018/3 at 23:05:44 on 21-May-2020 REM Old TITL 034360_jiali3_100K_b in C2/c REM SHELXT solution in C2/c: R1 0.108, Rweak 0.004, Alpha 0.018 REM 0.638 for 148 systematic absences, Orientation as input REM Formula found by SHELXT: C16 O3 CELL 1.54184 16.7429 10.5512 14.6971 90 93.247 90 ZERR 8 0.0001 0.0001 0.0001 0 0.001 0 LATT 7 SYMM -X,+Y,0.5-Z SFAC C H O UNIT 128 112 24 L.S. 10 0 0 PLAN 5 SIZE 0.06 0.1 0.15 CONF BOND list 4 MORE -1 BOND $H fmap 2 53 acta REM REM REM WGHT 0.040300 1.925200 FVAR 0.30974 O2 3 0.335443 0.390488 0.532886 11.00000 0.02396 0.01762 = 0.01589 -0.00335 0.00350 -0.00105 O1 3 0.425317 0.353484 0.656900 11.00000 0.01832 0.02001 = 0.02527 0.00627 0.00560 0.00559 O3 3 0.312193 0.493348 0.400434 11.00000 0.03114 0.03917 = 0.01451 -0.00155 -0.00069 -0.00291 C1 1 0.209357 0.430785 0.665398 11.00000 0.01758 0.01540 = 0.01557 0.00326 0.00410 -0.00250 C2 1 0.185173 0.534516 0.715882 11.00000 0.01901 0.01567 = 0.01602 0.00058 0.00097 -0.00295 AFIX 43 H2 2 0.220520 0.570139 0.759802 11.00000 -1.20000 AFIX 0 C3 1 0.108953 0.585257 0.701366 11.00000 0.02220 0.01588 = 0.01956 0.00091 0.00420 0.00027 AFIX 43 H3 2 0.093499 0.654363 0.735494 11.00000 -1.20000 AFIX 0 C4 1 0.055874 0.532687 0.635851 11.00000 0.01730 0.02549 = 0.02092 0.00401 0.00117 -0.00013 AFIX 43 H4 2 0.004596 0.565811 0.626446 11.00000 -1.20000 AFIX 0 C5 1 0.079710 0.430334 0.584383 11.00000 0.02176 0.02884 = 0.01794 -0.00173 -0.00084 -0.00659 AFIX 43 H5 2 0.044376 0.395390 0.540155 11.00000 -1.20000 AFIX 0 C6 1 0.156064 0.379968 0.598682 11.00000 0.02416 0.01971 = 0.01802 -0.00361 0.00499 -0.00394 AFIX 43 H6 2 0.171733 0.311986 0.563574 11.00000 -1.20000 AFIX 0 C7 1 0.290094 0.370606 0.686012 11.00000 0.02020 0.01528 = 0.01855 0.00295 0.00406 0.00102 AFIX 23 H7A 2 0.285192 0.279880 0.676609 11.00000 -1.20000 H7B 2 0.305632 0.384415 0.749826 11.00000 -1.20000 AFIX 0 C8 1 0.356449 0.420350 0.628615 11.00000 0.01814 0.01556 = 0.01461 -0.00060 0.00150 0.00226 C9 1 0.495612 0.384827 0.610539 11.00000 0.01872 0.02683 = 0.03174 0.00663 0.00732 0.00564 AFIX 137 H9A 2 0.488063 0.361524 0.547498 11.00000 -1.50000 H9B 2 0.540612 0.339641 0.637828 11.00000 -1.50000 H9C 2 0.505296 0.474332 0.615202 11.00000 -1.50000 AFIX 0 C10 1 0.328914 0.497777 0.481087 11.00000 0.01495 0.02436 = 0.01707 0.00015 0.00328 0.00050 C11 1 0.365840 0.562677 0.627642 11.00000 0.01310 0.01544 = 0.01715 0.00045 0.00388 0.00125 C12 1 0.347342 0.607257 0.540836 11.00000 0.01238 0.01973 = 0.01691 0.00143 0.00314 0.00110 C13 1 0.349666 0.735952 0.519948 11.00000 0.01593 0.02167 = 0.02423 0.00784 0.00529 0.00304 AFIX 43 H13 2 0.336081 0.765506 0.461494 11.00000 -1.20000 AFIX 0 C14 1 0.373075 0.817880 0.590000 11.00000 0.01899 0.01469 = 0.03680 0.00256 0.01004 0.00048 AFIX 43 H14 2 0.375176 0.904474 0.578573 11.00000 -1.20000 AFIX 0 C15 1 0.393566 0.772847 0.677415 11.00000 0.01889 0.02000 = 0.02920 -0.00786 0.00761 -0.00288 AFIX 43 H15 2 0.410333 0.829786 0.722875 11.00000 -1.20000 AFIX 0 C16 1 0.389416 0.644389 0.697945 11.00000 0.01828 0.02190 = 0.01682 -0.00188 0.00272 -0.00030 AFIX 43 H16 2 0.401970 0.614520 0.756552 11.00000 -1.20000 AFIX 0 HKLF 4 REM 034360_jiali3_100k_b_a.res in C2/c REM wR2 = 0.0855, GooF = S = 1.088, Restrained GooF = 1.088 for all data REM R1 = 0.0341 for 2455 Fo > 4sig(Fo) and 0.0350 for all 2550 data REM 173 parameters refined using 0 restraints END WGHT 0.0403 1.9252 REM Highest difference peak 0.209, deepest hole -0.291, 1-sigma level 0.049 Q1 1 0.3220 0.3992 0.6590 11.00000 0.05 0.21 Q2 1 0.3601 0.4941 0.6323 11.00000 0.05 0.20 Q3 1 0.1762 0.4033 0.6421 11.00000 0.05 0.18 Q4 1 0.3395 0.5597 0.5077 11.00000 0.05 0.17 Q5 1 0.3664 0.5870 0.5855 11.00000 0.05 0.15 ; _shelx_res_checksum 35561 _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 1.913 _oxdiff_exptl_absorpt_empirical_full_min 0.808 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -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 O2 O 0.33544(4) 0.39049(7) 0.53289(5) 0.01906(18) Uani 1 1 d . . . . . O1 O 0.42532(4) 0.35348(7) 0.65690(5) 0.02104(18) Uani 1 1 d . . . . . O3 O 0.31219(5) 0.49335(8) 0.40043(5) 0.0283(2) Uani 1 1 d . . . . . C1 C 0.20936(6) 0.43079(9) 0.66540(7) 0.0161(2) Uani 1 1 d . . . . . C2 C 0.18517(6) 0.53452(10) 0.71588(7) 0.0169(2) Uani 1 1 d . . . . . H2 H 0.220520 0.570139 0.759802 0.020 Uiso 1 1 calc R U . . . C3 C 0.10895(6) 0.58526(10) 0.70137(7) 0.0191(2) Uani 1 1 d . . . . . H3 H 0.093499 0.654363 0.735494 0.023 Uiso 1 1 calc R U . . . C4 C 0.05587(6) 0.53269(11) 0.63585(7) 0.0212(2) Uani 1 1 d . . . . . H4 H 0.004596 0.565811 0.626446 0.025 Uiso 1 1 calc R U . . . C5 C 0.07971(7) 0.43033(11) 0.58438(7) 0.0229(2) Uani 1 1 d . . . . . H5 H 0.044376 0.395390 0.540155 0.028 Uiso 1 1 calc R U . . . C6 C 0.15606(6) 0.37997(10) 0.59868(7) 0.0205(2) Uani 1 1 d . . . . . H6 H 0.171733 0.311986 0.563574 0.025 Uiso 1 1 calc R U . . . C7 C 0.29009(6) 0.37061(10) 0.68601(7) 0.0179(2) Uani 1 1 d . . . . . H7A H 0.285192 0.279880 0.676609 0.021 Uiso 1 1 calc R U . . . H7B H 0.305632 0.384415 0.749826 0.021 Uiso 1 1 calc R U . . . C8 C 0.35645(6) 0.42035(10) 0.62861(7) 0.0161(2) Uani 1 1 d . . . . . C9 C 0.49561(6) 0.38483(11) 0.61054(8) 0.0255(3) Uani 1 1 d . . . . . H9A H 0.488063 0.361524 0.547498 0.038 Uiso 1 1 calc R U . . . H9B H 0.540612 0.339641 0.637828 0.038 Uiso 1 1 calc R U . . . H9C H 0.505296 0.474332 0.615202 0.038 Uiso 1 1 calc R U . . . C10 C 0.32891(6) 0.49778(10) 0.48109(7) 0.0187(2) Uani 1 1 d . . . . . C11 C 0.36584(6) 0.56268(9) 0.62764(7) 0.0151(2) Uani 1 1 d . . . . . C12 C 0.34734(6) 0.60726(10) 0.54084(7) 0.0163(2) Uani 1 1 d . . . . . C13 C 0.34967(6) 0.73595(10) 0.51995(7) 0.0205(2) Uani 1 1 d . . . . . H13 H 0.336081 0.765506 0.461494 0.025 Uiso 1 1 calc R U . . . C14 C 0.37308(6) 0.81788(10) 0.59000(8) 0.0232(2) Uani 1 1 d . . . . . H14 H 0.375176 0.904474 0.578573 0.028 Uiso 1 1 calc R U . . . C15 C 0.39357(6) 0.77285(10) 0.67741(8) 0.0225(2) Uani 1 1 d . . . . . H15 H 0.410333 0.829786 0.722875 0.027 Uiso 1 1 calc R U . . . C16 C 0.38942(6) 0.64439(10) 0.69795(7) 0.0189(2) Uani 1 1 d . . . . . H16 H 0.401970 0.614520 0.756552 0.023 Uiso 1 1 calc R U . . . 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 O2 0.0240(4) 0.0176(4) 0.0159(4) -0.0034(3) 0.0035(3) -0.0011(3) O1 0.0183(4) 0.0200(4) 0.0253(4) 0.0063(3) 0.0056(3) 0.0056(3) O3 0.0311(4) 0.0392(5) 0.0145(4) -0.0015(3) -0.0007(3) -0.0029(4) C1 0.0176(5) 0.0154(5) 0.0156(5) 0.0033(4) 0.0041(4) -0.0025(4) C2 0.0190(5) 0.0157(5) 0.0160(5) 0.0006(4) 0.0010(4) -0.0029(4) C3 0.0222(5) 0.0159(5) 0.0196(5) 0.0009(4) 0.0042(4) 0.0003(4) C4 0.0173(5) 0.0255(5) 0.0209(5) 0.0040(4) 0.0012(4) -0.0001(4) C5 0.0218(5) 0.0288(6) 0.0179(5) -0.0017(4) -0.0008(4) -0.0066(4) C6 0.0242(5) 0.0197(5) 0.0180(5) -0.0036(4) 0.0050(4) -0.0039(4) C7 0.0202(5) 0.0153(5) 0.0186(5) 0.0030(4) 0.0041(4) 0.0010(4) C8 0.0181(5) 0.0156(5) 0.0146(5) -0.0006(4) 0.0015(4) 0.0023(4) C9 0.0187(5) 0.0268(6) 0.0317(6) 0.0066(5) 0.0073(4) 0.0056(4) C10 0.0149(5) 0.0244(6) 0.0171(5) 0.0002(4) 0.0033(4) 0.0005(4) C11 0.0131(4) 0.0154(5) 0.0171(5) 0.0004(4) 0.0039(4) 0.0013(4) C12 0.0124(4) 0.0197(5) 0.0169(5) 0.0014(4) 0.0031(4) 0.0011(4) C13 0.0159(5) 0.0217(5) 0.0242(5) 0.0078(4) 0.0053(4) 0.0030(4) C14 0.0190(5) 0.0147(5) 0.0368(6) 0.0026(4) 0.0100(4) 0.0005(4) C15 0.0189(5) 0.0200(5) 0.0292(6) -0.0079(4) 0.0076(4) -0.0029(4) C16 0.0183(5) 0.0219(5) 0.0168(5) -0.0019(4) 0.0027(4) -0.0003(4) 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' 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 C10 O2 C8 111.38(8) . . ? C8 O1 C9 115.42(8) . . ? C2 C1 C7 120.47(9) . . ? C6 C1 C2 118.82(10) . . ? C6 C1 C7 120.64(9) . . ? C1 C2 H2 119.6 . . ? C3 C2 C1 120.82(9) . . ? C3 C2 H2 119.6 . . ? C2 C3 H3 120.0 . . ? C4 C3 C2 119.93(10) . . ? C4 C3 H3 120.0 . . ? C3 C4 H4 120.1 . . ? C3 C4 C5 119.71(10) . . ? C5 C4 H4 120.1 . . ? C4 C5 H5 119.8 . . ? C6 C5 C4 120.33(10) . . ? C6 C5 H5 119.8 . . ? C1 C6 H6 119.8 . . ? C5 C6 C1 120.38(10) . . ? C5 C6 H6 119.8 . . ? C1 C7 H7A 108.6 . . ? C1 C7 H7B 108.6 . . ? C1 C7 C8 114.61(8) . . ? H7A C7 H7B 107.6 . . ? C8 C7 H7A 108.6 . . ? C8 C7 H7B 108.6 . . ? O2 C8 C7 108.32(8) . . ? O2 C8 C11 102.96(8) . . ? O1 C8 O2 109.08(8) . . ? O1 C8 C7 106.07(8) . . ? O1 C8 C11 114.90(8) . . ? C11 C8 C7 115.27(8) . . ? O1 C9 H9A 109.5 . . ? O1 C9 H9B 109.5 . . ? O1 C9 H9C 109.5 . . ? H9A C9 H9B 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O2 C10 C12 108.08(9) . . ? O3 C10 O2 121.60(10) . . ? O3 C10 C12 130.30(10) . . ? C12 C11 C8 109.27(9) . . ? C12 C11 C16 121.16(10) . . ? C16 C11 C8 129.57(9) . . ? C11 C12 C10 108.22(9) . . ? C11 C12 C13 121.93(10) . . ? C13 C12 C10 129.83(10) . . ? C12 C13 H13 121.5 . . ? C14 C13 C12 117.07(10) . . ? C14 C13 H13 121.5 . . ? C13 C14 H14 119.4 . . ? C13 C14 C15 121.14(10) . . ? C15 C14 H14 119.4 . . ? C14 C15 H15 119.4 . . ? C16 C15 C14 121.28(10) . . ? C16 C15 H15 119.4 . . ? C11 C16 C15 117.39(10) . . ? C11 C16 H16 121.3 . . ? C15 C16 H16 121.3 . . ? 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 O2 C8 1.4651(12) . ? O2 C10 1.3651(13) . ? O1 C8 1.3949(12) . ? O1 C9 1.4317(13) . ? O3 C10 1.2034(14) . ? C1 C2 1.3951(14) . ? C1 C6 1.3950(15) . ? C1 C7 1.5086(14) . ? C2 H2 0.9300 . ? C2 C3 1.3892(15) . ? C3 H3 0.9300 . ? C3 C4 1.3884(15) . ? C4 H4 0.9300 . ? C4 C5 1.3899(16) . ? C5 H5 0.9300 . ? C5 C6 1.3894(16) . ? C6 H6 0.9300 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C7 C8 1.5256(14) . ? C8 C11 1.5101(14) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C12 1.4731(15) . ? C11 C12 1.3784(14) . ? C11 C16 1.3858(15) . ? C12 C13 1.3932(15) . ? C13 H13 0.9300 . ? C13 C14 1.3839(16) . ? C14 H14 0.9300 . ? C14 C15 1.3943(17) . ? C15 H15 0.9300 . ? C15 C16 1.3912(16) . ? C16 H16 0.9300 . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C8 C11 C12 3.09(10) . . . . ? O2 C8 C11 C16 -176.37(9) . . . . ? O2 C10 C12 C11 0.89(11) . . . . ? O2 C10 C12 C13 179.15(10) . . . . ? O1 C8 C11 C12 121.55(9) . . . . ? O1 C8 C11 C16 -57.91(14) . . . . ? O3 C10 C12 C11 -177.62(11) . . . . ? O3 C10 C12 C13 0.65(19) . . . . ? C1 C2 C3 C4 -0.07(15) . . . . ? C1 C7 C8 O2 -62.63(11) . . . . ? C1 C7 C8 O1 -179.60(8) . . . . ? C1 C7 C8 C11 52.05(12) . . . . ? C2 C1 C6 C5 -1.39(15) . . . . ? C2 C1 C7 C8 -94.05(11) . . . . ? C2 C3 C4 C5 -0.74(16) . . . . ? C3 C4 C5 C6 0.48(16) . . . . ? C4 C5 C6 C1 0.60(16) . . . . ? C6 C1 C2 C3 1.13(15) . . . . ? C6 C1 C7 C8 89.14(12) . . . . ? C7 C1 C2 C3 -175.74(9) . . . . ? C7 C1 C6 C5 175.48(9) . . . . ? C7 C8 C11 C12 -114.63(10) . . . . ? C7 C8 C11 C16 65.91(14) . . . . ? C8 O2 C10 O3 179.85(9) . . . . ? C8 O2 C10 C12 1.18(11) . . . . ? C8 C11 C12 C10 -2.52(11) . . . . ? C8 C11 C12 C13 179.05(9) . . . . ? C8 C11 C16 C15 179.46(10) . . . . ? C9 O1 C8 O2 62.92(11) . . . . ? C9 O1 C8 C7 179.39(9) . . . . ? C9 O1 C8 C11 -52.05(12) . . . . ? C10 O2 C8 O1 -125.03(9) . . . . ? C10 O2 C8 C7 119.94(9) . . . . ? C10 O2 C8 C11 -2.57(10) . . . . ? C10 C12 C13 C14 -176.76(10) . . . . ? C11 C12 C13 C14 1.30(15) . . . . ? C12 C11 C16 C15 0.06(15) . . . . ? C12 C13 C14 C15 0.18(15) . . . . ? C13 C14 C15 C16 -1.55(16) . . . . ? C14 C15 C16 C11 1.40(15) . . . . ? C16 C11 C12 C10 176.99(9) . . . . ? C16 C11 C12 C13 -1.44(15) . . . . ?