#------------------------------------------------------------------------------ #$Date: 2019-06-14 03:11:14 +0300 (Fri, 14 Jun 2019) $ #$Revision: 215939 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/14/1551408.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_1551408 loop_ _publ_author_name 'Teng, Qi' 'Thirupathi, Nuligonda' 'Tung, Chen-Ho' 'Xu, Zhenghu' _publ_section_title ; Hydroalkynylative cyclization of 1,6-enynes with terminal alkynes ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/C9SC02341K _journal_year 2019 _chemical_formula_moiety 'C22 H18 O2' _chemical_formula_sum 'C22 H18 O2' _chemical_formula_weight 314.36 _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _audit_creation_date 2018-05-24 _audit_creation_method ; Olex2 1.2 (compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874) ; _audit_update_record ; 2018-05-24 deposited with the CCDC. 2019-06-10 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90.843(2) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 8.2170(2) _cell_length_b 7.7716(2) _cell_length_c 13.2349(3) _cell_measurement_reflns_used 5790 _cell_measurement_temperature 172.99(10) _cell_measurement_theta_max 76.3940 _cell_measurement_theta_min 5.3600 _cell_volume 845.08(4) _computing_cell_refinement 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_data_collection 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_data_reduction 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution ; Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008; Palatinus et al., 2012) ; _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 172.99(10) _diffrn_detector 'CCD plate' _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 0.983 _diffrn_measured_fraction_theta_max 0.997 _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 -74.00 -40.00 1.00 0.10 -- -48.45 -43.00 77.00 34 2 \w -115.00 -83.00 1.00 0.10 -- -48.45 -43.00 77.00 32 3 \w -49.00 1.00 1.00 0.10 -- -48.45 43.00-131.00 50 4 \w -155.00 -73.00 1.00 0.10 -- -86.25 -43.00 77.00 82 5 \w -81.00 -56.00 1.00 0.10 -- -86.25 43.00-131.00 25 6 \w 94.00 125.00 1.00 0.10 -- 107.75 43.00-131.00 31 7 \w 37.00 119.00 1.00 0.10 -- 107.75 -43.00 77.00 82 8 \w 131.00 161.00 1.00 0.10 -- 107.75 43.00-131.00 30 9 \w -115.00 -89.00 1.00 0.10 -- -48.45-125.00-150.00 26 10 \w -120.00 -27.00 1.00 0.10 -- -48.45 -77.00 0.00 93 11 \w -8.00 25.00 1.00 0.10 -- 48.45 -43.00 77.00 33 12 \w 41.00 68.00 1.00 0.10 -- 48.45 43.00-131.00 27 13 \w -145.00-105.00 1.00 0.10 -- -86.25 -77.00 30.00 40 14 \w -94.00 -64.00 1.00 0.10 -- -86.25 -77.00 30.00 30 15 \w -151.00-106.00 1.00 0.10 -- -86.25 -77.00 -30.00 45 16 \w -98.00 -14.00 1.00 0.10 -- -86.25 57.00 60.00 84 17 \w -139.00 -64.00 1.00 0.10 -- -86.25 -77.00 0.00 75 18 \w -103.00 -64.00 1.00 0.10 -- -86.25 -77.00 -30.00 39 19 \w -127.00 -71.00 1.00 0.10 -- -86.25 -69.00 -51.84 56 20 \w 75.00 109.00 1.00 0.10 -- 107.75 -99.00 -90.00 34 21 \w 39.00 64.00 1.00 0.10 -- 107.75 -99.00 -90.00 25 22 \w 94.00 165.00 1.00 0.10 -- 107.75 57.00 -60.00 71 23 \w 35.00 72.00 1.00 0.10 -- 107.75 -37.00-120.00 37 24 \w 33.00 116.00 1.00 0.10 -- 107.75 -19.00-120.00 83 25 \w 144.00 177.00 1.00 0.10 -- 107.75 77.00 0.00 33 26 \w 85.00 139.00 1.00 0.10 -- 107.75 77.00 0.00 54 27 \w 80.00 105.00 1.00 0.10 -- 107.75 -37.00-120.00 25 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy, Dualflex, HyPix' _diffrn_measurement_method '\w scans' _diffrn_measurement_specimen_support 'Mitegen 50um' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.1635935000 _diffrn_orient_matrix_UB_12 0.0954745000 _diffrn_orient_matrix_UB_13 0.0081027000 _diffrn_orient_matrix_UB_21 -0.0083594000 _diffrn_orient_matrix_UB_22 -0.0490688000 _diffrn_orient_matrix_UB_23 0.1125816000 _diffrn_orient_matrix_UB_31 0.0911354000 _diffrn_orient_matrix_UB_32 0.1667225000 _diffrn_orient_matrix_UB_33 0.0284845000 _diffrn_radiation_collimation 0.3 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0510 _diffrn_reflns_av_unetI/netI 0.0362 _diffrn_reflns_Laue_measured_fraction_full 0.983 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 7597 _diffrn_reflns_point_group_measured_fraction_full 0.967 _diffrn_reflns_point_group_measured_fraction_max 0.980 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 67.059 _diffrn_reflns_theta_min 5.384 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_current 24.0 _diffrn_source_power 1.2 _diffrn_source_target Mo _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _diffrn_source_voltage 50.0 _exptl_absorpt_coefficient_mu 0.615 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.11302 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light yellow' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.235 _exptl_crystal_description block _exptl_crystal_F_000 332 _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.09 _refine_diff_density_max 0.207 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.049 _refine_ls_abs_structure_details ; Flack x determined using 1195 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons and Flack (2004), Acta Cryst. A60, s61). ; _refine_ls_abs_structure_Flack 0.25(17) _refine_ls_extinction_coef 0.020(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 219 _refine_ls_number_reflns 2960 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.058 _refine_ls_R_factor_all 0.0456 _refine_ls_R_factor_gt 0.0424 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0704P)^2^+0.1237P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1090 _refine_ls_wR_factor_ref 0.1187 _reflns_Friedel_coverage 0.822 _reflns_Friedel_fraction_full 0.947 _reflns_Friedel_fraction_max 0.961 _reflns_number_gt 2783 _reflns_number_total 2960 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9sc02341k2.cif _cod_data_source_block 180524b _cod_database_code 1551408 _shelxl_version_number 2013-4 _chemical_oxdiff_formula CO _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 0.947 _shelx_estimated_absorpt_t_min 0.930 _diffrn_oxdiff_ac3_digest_frames ; 01a97c5b6ba7fcd4e197ed9a279689ed05012769872 ; _diffrn_oxdiff_ac3_digest_hkl ; 014ae1318d0c73ec81b3d262e2c60dc4c685a2 ; _reflns_odcompleteness_completeness 99.69 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Others Fixed Uiso: H1A(0.08) H1B(0.08) H1C(0.08) H3(0.047) H4(0.051) H6A(0.041) H6B(0.041) H7(0.036) H9A(0.045) H9B(0.045) H10(0.04) H14(0.045) H15(0.044) H18(0.041) H19(0.051) H20(0.055) H21(0.055) H22(0.047) Fixed X: H1A(0.5719) H1B(0.5535) H1C(0.6244) H3(0.4044) H4(0.2098) H6A(0.0764) H6B(0.2521) H7(0.2876) H9A(0.1864) H9B(0.1561) H10(-0.0796) H14(- 0.0264) H15(-0.1469) H18(-0.4432) H19(-0.6901) H20(-0.809) H21(-0.6594) H22(- 0.3924) Fixed Y: H1A(-0.7179) H1B(-0.5175) H1C(-0.6013) H3(-0.4714) H4(-0.2804) H6A(- 0.5046) H6B(-0.4264) H7(-0.7145) H9A(-0.9475) H9B(-0.7628) H10(-0.899) H14(- 0.5967) H15(-0.5326) H18(-0.8075) H19(-0.8046) H20(-0.741) H21(-0.608) H22(- 0.5379) Fixed Z: H1A(-0.7895) H1B(-0.7824) H1C(-0.88) H3(-1.0004) H4(-0.9792) H6A(- 0.7164) H6B(-0.712) H7(-0.7359) H9A(-0.9563) H9B(-1.0024) H10(-0.8576) H14(- 0.4779) H15(-0.3292) H18(-0.5832) H19(-0.4754) H20(-0.3251) H21(-0.1959) H22(- 0.2181) ; _shelx_res_file ; TITL 180524B in P2 CELL 1.54184 8.216984 7.771603 13.23488 90 90.843 90 ZERR 2 0.000199 0.000201 0.000349 0 0.0023 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H O UNIT 44 36 4 L.S. 4 0 0 PLAN 10 SIZE 0.09 0.1 0.12 fmap 2 53 acta SHEL 999 0.837 OMIT 8 3 7 OMIT 1 9 2 OMIT -3 3 14 OMIT 9 3 3 OMIT -9 -1 4 OMIT 1 9 3 REM REM REM WGHT 0.070400 0.123700 EXTI 0.020179 FVAR 12.18597 C1 1 0.547322 -0.614966 -0.826811 11.00000 0.03097 0.06740 = 0.06104 -0.00399 -0.00376 -0.00332 AFIX 137 H1A 2 0.571891 -0.717894 -0.789494 11.00000 -1.50000 H1B 2 0.553464 -0.517505 -0.782351 11.00000 -1.50000 H1C 2 0.624406 -0.601338 -0.880027 11.00000 -1.50000 AFIX 0 C2 1 0.377012 -0.627861 -0.871932 11.00000 0.02836 0.03937 = 0.03449 -0.00232 0.00434 -0.00087 C3 1 0.341352 -0.480562 -0.942844 11.00000 0.04452 0.04115 = 0.03302 0.00245 0.01020 -0.00747 AFIX 43 H3 2 0.404383 -0.471404 -1.000386 11.00000 -1.20000 AFIX 0 C4 1 0.226881 -0.363091 -0.929340 11.00000 0.05654 0.03380 = 0.03581 0.00411 -0.00378 -0.00431 AFIX 43 H4 2 0.209803 -0.280439 -0.979193 11.00000 -1.20000 AFIX 0 C5 1 0.126686 -0.358276 -0.839466 11.00000 0.04340 0.02873 = 0.04321 -0.00839 -0.00216 -0.00270 C6 1 0.172145 -0.481011 -0.756068 11.00000 0.04290 0.02871 = 0.03185 -0.00668 0.00671 -0.00329 AFIX 23 H6A 2 0.076400 -0.504553 -0.716351 11.00000 -1.20000 H6B 2 0.252094 -0.426397 -0.711980 11.00000 -1.20000 AFIX 0 C7 1 0.241796 -0.652053 -0.793965 11.00000 0.03205 0.03013 = 0.02749 0.00002 0.00057 0.00098 AFIX 13 H7 2 0.287649 -0.714522 -0.735865 11.00000 -1.20000 AFIX 0 C8 1 0.123320 -0.769602 -0.848629 11.00000 0.03349 0.02736 = 0.03055 -0.00121 -0.00350 0.00180 C9 1 0.201615 -0.825188 -0.945114 11.00000 0.03996 0.03687 = 0.03614 -0.00885 0.00245 -0.00266 AFIX 23 H9A 2 0.186403 -0.947528 -0.956283 11.00000 -1.20000 H9B 2 0.156146 -0.762784 -1.002381 11.00000 -1.20000 AFIX 0 C10 1 -0.020029 -0.825877 -0.815470 11.00000 0.03159 0.03160 = 0.03560 -0.00159 -0.00257 -0.00193 AFIX 43 H10 2 -0.079615 -0.898989 -0.857563 11.00000 -1.20000 AFIX 0 C11 1 -0.088321 -0.782491 -0.720783 11.00000 0.02485 0.03725 = 0.04181 0.00601 -0.00244 -0.00191 C12 1 -0.148815 -0.751222 -0.640756 11.00000 0.02911 0.03527 = 0.04148 0.00533 0.00027 -0.00272 C13 1 -0.224418 -0.711022 -0.547156 11.00000 0.03576 0.02980 = 0.03424 0.00476 -0.00182 0.00038 C14 1 -0.134872 -0.625705 -0.468371 11.00000 0.03228 0.03414 = 0.04462 0.00567 -0.00716 -0.00385 AFIX 43 H14 2 -0.026371 -0.596701 -0.477905 11.00000 -1.20000 AFIX 0 C15 1 -0.207334 -0.586890 -0.379862 11.00000 0.04149 0.03060 = 0.03762 0.00221 -0.01268 -0.00188 AFIX 43 H15 2 -0.146852 -0.532597 -0.329194 11.00000 -1.20000 AFIX 0 C16 1 -0.372321 -0.626788 -0.362626 11.00000 0.04106 0.02154 = 0.03289 0.00374 -0.00591 0.00137 C17 1 -0.463194 -0.711232 -0.440706 11.00000 0.03430 0.02850 = 0.03285 0.00021 -0.00136 -0.00187 C18 1 -0.384755 -0.751841 -0.532097 11.00000 0.03441 0.03502 = 0.03195 -0.00169 0.00033 -0.00565 AFIX 43 H18 2 -0.443187 -0.807494 -0.583167 11.00000 -1.20000 AFIX 0 C19 1 -0.629234 -0.751611 -0.424387 11.00000 0.03918 0.04676 = 0.04185 -0.00244 0.00306 -0.00581 AFIX 43 H19 2 -0.690096 -0.804571 -0.475371 11.00000 -1.20000 AFIX 0 C20 1 -0.700179 -0.713577 -0.334879 11.00000 0.04577 0.04535 = 0.04641 0.00103 0.01028 -0.00101 AFIX 43 H20 2 -0.808972 -0.741031 -0.325082 11.00000 -1.20000 AFIX 0 C21 1 -0.609907 -0.632847 -0.256897 11.00000 0.06148 0.04017 = 0.03542 -0.00089 0.01132 0.00826 AFIX 43 H21 2 -0.659398 -0.608028 -0.195856 11.00000 -1.20000 AFIX 0 C22 1 -0.450566 -0.590867 -0.270283 11.00000 0.05680 0.02895 = 0.03207 -0.00096 -0.00406 0.00488 AFIX 43 H22 2 -0.392428 -0.537927 -0.218092 11.00000 -1.20000 AFIX 0 O1 3 0.370852 -0.785039 -0.930819 11.00000 0.03760 0.03997 = 0.04392 -0.00632 0.00832 0.00522 O2 3 0.014987 -0.255459 -0.831135 11.00000 0.05666 0.04474 = 0.06079 -0.00962 -0.00446 0.01595 HKLF 4 REM 180524B in P2 REM R1 = 0.0424 for 2783 Fo > 4sig(Fo) and 0.0456 for all 2960 data REM 219 parameters refined using 1 restraints END WGHT 0.0704 0.1238 REM Highest difference peak 0.207, deepest hole -0.217, 1-sigma level 0.049 Q1 1 -0.1631 -0.8290 -0.6841 11.00000 0.05 0.21 Q2 1 -0.0602 -0.7342 -0.6660 11.00000 0.05 0.19 Q3 1 -0.3168 -0.6041 -0.3766 11.00000 0.05 0.17 Q4 1 -0.1773 -0.7587 -0.6226 11.00000 0.05 0.17 Q5 1 -0.2044 -0.6433 -0.5884 11.00000 0.05 0.17 Q6 1 0.0006 -0.5372 -0.5245 11.00000 0.05 0.16 Q7 1 -0.0732 -0.6248 -0.5649 11.00000 0.05 0.16 Q8 1 0.2117 -0.3221 -0.8818 11.00000 0.05 0.16 Q9 1 0.0039 -0.7546 -0.7519 11.00000 0.05 0.15 Q10 1 0.4614 -0.8172 -0.9653 11.00000 0.05 0.15 ; _shelx_res_checksum 71882 _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 3.909 _oxdiff_exptl_absorpt_empirical_full_min 0.503 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -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 C1 C 0.5473(4) -0.6150(6) -0.8268(3) 0.0532(9) Uani 1 1 d . H1A H 0.5719 -0.7179 -0.7895 0.080 Uiso 1 1 calc GR H1B H 0.5535 -0.5175 -0.7824 0.080 Uiso 1 1 calc GR H1C H 0.6244 -0.6013 -0.8800 0.080 Uiso 1 1 calc GR C2 C 0.3770(3) -0.6279(4) -0.8719(2) 0.0340(6) Uani 1 1 d . C3 C 0.3414(4) -0.4806(5) -0.9428(2) 0.0395(7) Uani 1 1 d . H3 H 0.4044 -0.4714 -1.0004 0.047 Uiso 1 1 calc R C4 C 0.2269(4) -0.3631(4) -0.9293(2) 0.0421(7) Uani 1 1 d . H4 H 0.2098 -0.2804 -0.9792 0.051 Uiso 1 1 calc R C5 C 0.1267(4) -0.3583(4) -0.8395(2) 0.0385(7) Uani 1 1 d . C6 C 0.1721(4) -0.4810(4) -0.7561(2) 0.0344(7) Uani 1 1 d . H6A H 0.0764 -0.5046 -0.7164 0.041 Uiso 1 1 calc R H6B H 0.2521 -0.4264 -0.7120 0.041 Uiso 1 1 calc R C7 C 0.2418(3) -0.6521(4) -0.79397(19) 0.0299(6) Uani 1 1 d . H7 H 0.2876 -0.7145 -0.7359 0.036 Uiso 1 1 calc R C8 C 0.1233(3) -0.7696(4) -0.8486(2) 0.0305(6) Uani 1 1 d . C9 C 0.2016(4) -0.8252(4) -0.9451(2) 0.0376(7) Uani 1 1 d . H9A H 0.1864 -0.9475 -0.9563 0.045 Uiso 1 1 calc R H9B H 0.1561 -0.7628 -1.0024 0.045 Uiso 1 1 calc R C10 C -0.0200(3) -0.8259(4) -0.8155(2) 0.0330(6) Uani 1 1 d . H10 H -0.0796 -0.8990 -0.8576 0.040 Uiso 1 1 calc R C11 C -0.0883(3) -0.7825(4) -0.7208(2) 0.0347(6) Uani 1 1 d . C12 C -0.1488(3) -0.7512(4) -0.6408(2) 0.0353(6) Uani 1 1 d . C13 C -0.2244(3) -0.7110(4) -0.5472(2) 0.0333(6) Uani 1 1 d . C14 C -0.1349(3) -0.6257(4) -0.4684(2) 0.0371(6) Uani 1 1 d . H14 H -0.0264 -0.5967 -0.4779 0.045 Uiso 1 1 calc R C15 C -0.2073(4) -0.5869(4) -0.3799(2) 0.0367(7) Uani 1 1 d . H15 H -0.1469 -0.5326 -0.3292 0.044 Uiso 1 1 calc R C16 C -0.3723(3) -0.6268(4) -0.3626(2) 0.0319(6) Uani 1 1 d . C17 C -0.4632(3) -0.7112(4) -0.4407(2) 0.0319(6) Uani 1 1 d . C18 C -0.3848(3) -0.7518(4) -0.5321(2) 0.0338(6) Uani 1 1 d . H18 H -0.4432 -0.8075 -0.5832 0.041 Uiso 1 1 calc R C19 C -0.6292(4) -0.7516(5) -0.4244(2) 0.0426(7) Uani 1 1 d . H19 H -0.6901 -0.8046 -0.4754 0.051 Uiso 1 1 calc R C20 C -0.7002(4) -0.7136(5) -0.3349(2) 0.0457(8) Uani 1 1 d . H20 H -0.8090 -0.7410 -0.3251 0.055 Uiso 1 1 calc R C21 C -0.6099(4) -0.6328(5) -0.2569(2) 0.0456(8) Uani 1 1 d . H21 H -0.6594 -0.6080 -0.1959 0.055 Uiso 1 1 calc R C22 C -0.4506(4) -0.5909(4) -0.2703(2) 0.0393(7) Uani 1 1 d . H22 H -0.3924 -0.5379 -0.2181 0.047 Uiso 1 1 calc R O1 O 0.3709(2) -0.7850(3) -0.93082(15) 0.0404(5) Uani 1 1 d . O2 O 0.0150(3) -0.2555(3) -0.83113(18) 0.0541(7) 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 C1 0.0310(15) 0.067(2) 0.061(2) -0.0040(19) -0.0038(13) -0.0033(16) C2 0.0284(13) 0.0394(16) 0.0345(13) -0.0023(13) 0.0043(10) -0.0009(12) C3 0.0445(17) 0.0412(17) 0.0330(15) 0.0025(13) 0.0102(12) -0.0075(13) C4 0.0565(18) 0.0338(17) 0.0358(15) 0.0041(13) -0.0038(13) -0.0043(14) C5 0.0434(16) 0.0287(15) 0.0432(15) -0.0084(13) -0.0022(13) -0.0027(13) C6 0.0429(15) 0.0287(15) 0.0318(14) -0.0067(12) 0.0067(12) -0.0033(12) C7 0.0320(13) 0.0301(14) 0.0275(12) 0.0000(11) 0.0006(10) 0.0010(11) C8 0.0335(13) 0.0274(14) 0.0306(12) -0.0012(11) -0.0035(10) 0.0018(11) C9 0.0400(15) 0.0369(17) 0.0361(15) -0.0088(13) 0.0025(12) -0.0027(12) C10 0.0316(13) 0.0316(15) 0.0356(14) -0.0016(12) -0.0026(11) -0.0019(11) C11 0.0248(12) 0.0373(15) 0.0418(15) 0.0060(13) -0.0024(11) -0.0019(11) C12 0.0291(13) 0.0353(15) 0.0415(15) 0.0053(12) 0.0003(11) -0.0027(11) C13 0.0358(14) 0.0298(14) 0.0342(13) 0.0048(12) -0.0018(11) 0.0004(11) C14 0.0323(13) 0.0341(15) 0.0446(15) 0.0057(14) -0.0072(11) -0.0038(13) C15 0.0415(15) 0.0306(15) 0.0376(15) 0.0022(12) -0.0127(12) -0.0019(11) C16 0.0411(14) 0.0215(13) 0.0329(13) 0.0037(11) -0.0059(11) 0.0014(11) C17 0.0343(14) 0.0285(14) 0.0328(13) 0.0002(11) -0.0014(11) -0.0019(11) C18 0.0344(13) 0.0350(15) 0.0320(14) -0.0017(12) 0.0003(11) -0.0057(11) C19 0.0392(15) 0.0468(19) 0.0419(16) -0.0024(14) 0.0031(12) -0.0058(13) C20 0.0458(17) 0.0453(19) 0.0464(17) 0.0010(15) 0.0103(14) -0.0010(14) C21 0.0615(19) 0.0402(17) 0.0354(15) -0.0009(14) 0.0113(14) 0.0083(16) C22 0.0568(18) 0.0290(15) 0.0321(14) -0.0010(12) -0.0041(12) 0.0049(13) O1 0.0376(11) 0.0400(12) 0.0439(11) -0.0063(10) 0.0083(9) 0.0052(10) O2 0.0567(14) 0.0447(14) 0.0608(14) -0.0096(12) -0.0045(11) 0.0160(11) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 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 C1 C2 C7 114.5(2) C3 C2 C1 111.4(3) C3 C2 C7 112.0(2) O1 C2 C1 107.0(3) O1 C2 C3 107.5(2) O1 C2 C7 103.8(2) C4 C3 C2 124.9(3) C3 C4 C5 122.6(3) C4 C5 C6 116.5(3) O2 C5 C4 121.6(3) O2 C5 C6 121.8(3) C5 C6 C7 113.6(2) C6 C7 C2 112.9(2) C8 C7 C2 102.7(2) C8 C7 C6 116.1(2) C9 C8 C7 107.4(2) C10 C8 C7 127.2(2) C10 C8 C9 125.1(3) O1 C9 C8 104.6(2) C8 C10 C11 125.0(3) C12 C11 C10 177.7(3) C11 C12 C13 178.3(3) C12 C13 C14 120.5(2) C18 C13 C12 120.4(3) C18 C13 C14 119.1(3) C15 C14 C13 120.3(2) C14 C15 C16 121.7(3) C15 C16 C17 118.5(3) C15 C16 C22 123.0(3) C22 C16 C17 118.4(2) C18 C17 C16 118.8(2) C18 C17 C19 122.1(3) C19 C17 C16 119.1(3) C13 C18 C17 121.5(3) C20 C19 C17 120.6(3) C19 C20 C21 120.4(3) C22 C21 C20 120.5(3) C21 C22 C16 120.9(3) C9 O1 C2 106.3(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C2 1.517(4) C2 C3 1.506(4) C2 C7 1.539(3) C2 O1 1.449(4) C3 C4 1.325(5) C4 C5 1.457(4) C5 C6 1.502(4) C5 O2 1.223(4) C6 C7 1.534(4) C7 C8 1.512(4) C8 C9 1.502(4) C8 C10 1.337(4) C9 O1 1.435(4) C10 C11 1.421(4) C11 C12 1.201(4) C12 C13 1.429(4) C13 C14 1.430(4) C13 C18 1.373(4) C14 C15 1.356(4) C15 C16 1.413(4) C16 C17 1.426(4) C16 C22 1.417(4) C17 C18 1.415(4) C17 C19 1.420(4) C19 C20 1.360(4) C20 C21 1.409(5) C21 C22 1.363(5)