#------------------------------------------------------------------------------ #$Date: 2024-04-19 06:02:04 +0300 (Fri, 19 Apr 2024) $ #$Revision: 291283 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/99/7159906.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_7159906 loop_ _publ_author_name 'Nguyen, Cao Nguyen' 'Nguyen, Duc Toan' 'Tran, Ha An' 'Mac, Hung Dinh' 'Nguyen, Thi Thu Tram' 'Retailleau, Pascal' 'Nguyen, Thanh Binh' _publ_section_title ; Base- and Sulfur- Promoted Oxidative Lactonization of Chalcone-Acetate Michael Adducts: Access to Pyran-2-ones ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D4OB00479E _journal_year 2024 _chemical_formula_moiety 'C24 H18 O2' _chemical_formula_sum 'C24 H18 O2' _chemical_formula_weight 338.38 _chemical_name_systematic 4,6-diphenyl-3-(p-tolyl)-2H-pyran-2-one _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 other _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2019/3 _audit_update_record ; 2023-11-30 deposited with the CCDC. 2024-04-18 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 114.575(12) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.459(4) _cell_length_b 18.500(7) _cell_length_c 11.372(4) _cell_measurement_reflns_used 1289 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 49.4 _cell_measurement_theta_min 7.0 _cell_volume 1809.7(12) _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014) ; _computing_data_collection ; CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014) ; _computing_structure_refinement 'SHELXL-2019/2 (Sheldrick, 2015b)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2015a)' _diffrn_ambient_temperature 293(2) _diffrn_detector 'Rapid 2 curved Imaging Plate' _diffrn_detector_area_resol_mean 10.0000 _diffrn_measured_fraction_theta_full 0.985 _diffrn_measured_fraction_theta_max 0.985 _diffrn_measurement_device ; Crystal Goniometer chi partial ; _diffrn_measurement_device_type ; Rigaku Spider ; _diffrn_measurement_method 'profile data from \w-scans' _diffrn_measurement_specimen_support Fiber _diffrn_radiation_monochromator 'Confocal CMF Osmic' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54187 _diffrn_reflns_av_R_equivalents 0.1269 _diffrn_reflns_av_unetI/netI 0.0930 _diffrn_reflns_Laue_measured_fraction_full 0.985 _diffrn_reflns_Laue_measured_fraction_max 0.985 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 14152 _diffrn_reflns_point_group_measured_fraction_full 0.985 _diffrn_reflns_point_group_measured_fraction_max 0.985 _diffrn_reflns_theta_full 55.984 _diffrn_reflns_theta_max 55.984 _diffrn_reflns_theta_min 7.030 _diffrn_source 'Rotating Anode mm007HF' _exptl_absorpt_coefficient_mu 0.614 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.608 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Abscor (Higashi, Rigaku, 1998)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.242 _exptl_crystal_description platelet _exptl_crystal_F_000 712 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CDCl3' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.03 _refine_diff_density_max 0.213 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.048 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 236 _refine_ls_number_reflns 2317 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.023 _refine_ls_R_factor_all 0.0944 _refine_ls_R_factor_gt 0.0640 _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^)+(0.0962P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1492 _refine_ls_wR_factor_ref 0.1895 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1401 _reflns_number_total 2319 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ob00479e2.cif _cod_data_source_block BN7550 _cod_depositor_comments ; The following automatic conversions were performed: data item '_exptl_absorpt_correction_type' value 'Multi-scan' was changed to 'multi-scan' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas ; _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7159906 _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_res_file ; TITL shelx_a.res in P-1 New: P21/n shelx.res created by SHELXL-2019/3 at 11:00:19 on 30-Nov-2023 CELL 1.54187 9.4590 18.5000 11.3720 90.000 114.575 90.000 ZERR 4 0.0040 0.0070 0.0040 0.000 0.012 0.000 LATT 1 SYMM 0.50000 - X , 0.50000 + Y , 0.50000 - Z SFAC C H O UNIT 96 72 8 LIST 4 ! automatically inserted. Change 6 to 4 for CHECKCIF!! L.S. 20 OMIT 7 4 1 OMIT 7 2 2 FMAP 2 PLAN -20 ACTA BOND $H SHEL 999 0.93 CONF HTAB REM EXTI 0.001402 REM EXTI 0.000912 WGHT 0.096200 FVAR 0.52246 O1 3 0.120391 0.025033 0.283390 11.00000 0.07366 0.06277 = 0.05346 0.00579 0.02477 -0.00151 C1 1 0.226980 -0.020552 0.504506 11.00000 0.05741 0.05520 = 0.04633 0.00026 0.02342 0.00059 C6 1 0.236416 -0.080827 0.592240 11.00000 0.05828 0.04975 = 0.05520 -0.00514 0.02745 0.00182 C5 1 0.126050 -0.029799 0.368700 11.00000 0.06724 0.06197 = 0.05747 0.00312 0.03073 0.00305 C4 1 0.213004 0.085570 0.324401 11.00000 0.07028 0.05705 = 0.05956 -0.00101 0.03735 -0.00026 C3 1 0.305444 0.094314 0.448888 11.00000 0.07699 0.05442 = 0.05668 0.00160 0.03509 -0.00506 AFIX 43 H3 2 0.366361 0.135724 0.475101 11.00000 -1.20000 AFIX 0 C2 1 0.313622 0.041835 0.543293 11.00000 0.05467 0.05651 = 0.04744 -0.00030 0.02364 0.00407 O2 3 0.044437 -0.081739 0.317437 11.00000 0.09666 0.06801 = 0.06784 -0.00899 0.02712 -0.01862 C9 1 0.255048 -0.195426 0.761796 11.00000 0.09764 0.05215 = 0.05718 -0.00049 0.03487 0.00213 C8 1 0.113588 -0.172164 0.667469 11.00000 0.08594 0.06405 = 0.07519 -0.00041 0.04541 -0.01014 AFIX 43 H8 2 0.023051 -0.195068 0.660837 11.00000 -1.20000 AFIX 0 C7 1 0.102102 -0.116435 0.583251 11.00000 0.06305 0.05869 = 0.07184 0.00055 0.03300 0.00148 AFIX 43 H7 2 0.005425 -0.102672 0.520849 11.00000 -1.20000 AFIX 0 C16 1 0.619249 0.090504 0.934232 11.00000 0.11939 0.08831 = 0.06371 -0.01456 0.03223 -0.00671 AFIX 43 H16 2 0.686141 0.099901 1.019773 11.00000 -1.20000 AFIX 0 C15 1 0.464319 0.074987 0.901131 11.00000 0.12579 0.08017 = 0.06839 -0.00783 0.05739 -0.00299 AFIX 43 H15 2 0.426698 0.075854 0.964772 11.00000 -1.20000 AFIX 0 C14 1 0.364802 0.058310 0.776113 11.00000 0.09142 0.06599 = 0.06197 -0.00518 0.04557 -0.00371 AFIX 43 H14 2 0.261589 0.046873 0.756101 11.00000 -1.20000 AFIX 0 C13 1 0.418625 0.058600 0.680363 11.00000 0.07478 0.04464 = 0.05135 0.00043 0.03008 0.00088 C12 1 0.265226 -0.256136 0.852983 11.00000 0.16671 0.06685 = 0.08823 0.01569 0.05124 -0.01488 AFIX 137 H12A 2 0.343847 -0.289771 0.855775 11.00000 -1.50000 H12B 2 0.166787 -0.280428 0.823411 11.00000 -1.50000 H12C 2 0.291538 -0.236953 0.937956 11.00000 -1.50000 AFIX 0 C11 1 0.379362 -0.105126 0.685747 11.00000 0.06684 0.05479 = 0.06677 -0.00134 0.03177 0.00442 AFIX 43 H11 2 0.470664 -0.083159 0.692012 11.00000 -1.20000 AFIX 0 C10 1 0.387251 -0.160569 0.768062 11.00000 0.08706 0.05535 = 0.06535 0.00174 0.03013 0.00822 AFIX 43 H10 2 0.483823 -0.175106 0.829616 11.00000 -1.20000 AFIX 0 C18 1 0.572158 0.076876 0.714024 11.00000 0.07648 0.07440 = 0.06213 -0.01042 0.03535 -0.01071 AFIX 43 H18 2 0.608783 0.079142 0.649838 11.00000 -1.20000 AFIX 0 C17 1 0.672613 0.091846 0.839907 11.00000 0.07740 0.09505 = 0.07050 -0.01544 0.02388 -0.01729 AFIX 43 H17 2 0.776159 0.102795 0.860374 11.00000 -1.20000 AFIX 0 C20 1 0.239589 0.205615 0.240990 11.00000 0.10485 0.06640 = 0.07139 0.01189 0.04711 0.00922 AFIX 43 H20 2 0.278377 0.223476 0.324997 11.00000 -1.20000 AFIX 0 C19 1 0.193055 0.134270 0.217187 11.00000 0.06905 0.06795 = 0.05077 0.00896 0.03142 0.00705 C21 1 0.228739 0.250438 0.140655 11.00000 0.12046 0.07048 = 0.09287 0.02113 0.06010 0.01545 AFIX 43 H21 2 0.261174 0.298273 0.157392 11.00000 -1.20000 AFIX 0 C24 1 0.134134 0.109015 0.091582 11.00000 0.09259 0.08775 = 0.06845 0.01028 0.03867 -0.00709 AFIX 43 H24 2 0.101466 0.061244 0.074139 11.00000 -1.20000 AFIX 0 C23 1 0.123446 0.154479 -0.008559 11.00000 0.10136 0.11825 = 0.05908 0.01110 0.03315 -0.00532 AFIX 43 H23 2 0.084292 0.137185 -0.092950 11.00000 -1.20000 AFIX 0 C22 1 0.170607 0.224873 0.016944 11.00000 0.10848 0.09880 = 0.09061 0.03279 0.05609 0.01285 AFIX 43 H22 2 0.163012 0.255444 -0.050348 11.00000 -1.20000 AFIX 0 HKLF 4 1 -1.0000 0.0000 0.0000 0.0000 -1.0000 0.0000 0.5000 0.0000 0.5000 REM shelx_a.res in P-1 New: P21/n REM wR2 = 0.1895, GooF = S = 1.023, Restrained GooF = 1.023 for all data REM R1 = 0.0640 for 1401 Fo > 4sig(Fo) and 0.0944 for all 2317 data REM 236 parameters refined using 0 restraints END WGHT 0.0950 0.0000 REM No hydrogen bonds found for HTAB generation REM Highest difference peak 0.213, deepest hole -0.237, 1-sigma level 0.048 Q1 1 0.4084 -0.2536 0.9625 11.00000 0.05 0.19 Q2 1 0.2205 0.0353 0.4186 11.00000 0.05 0.18 Q3 1 0.1375 -0.0848 0.4581 11.00000 0.05 0.18 Q4 1 0.0362 0.0233 0.1382 11.00000 0.05 0.18 Q5 1 0.1370 0.0887 0.3617 11.00000 0.05 0.18 Q6 1 0.3879 0.0882 0.3781 11.00000 0.05 0.16 Q7 1 0.1581 -0.1145 0.5606 11.00000 0.05 0.16 Q8 1 0.5302 0.0122 0.9078 11.00000 0.05 0.15 Q9 1 0.0934 -0.0002 -0.0039 11.00000 0.05 0.15 Q10 1 0.1897 -0.2503 0.9301 11.00000 0.05 0.15 Q11 1 0.2286 0.1579 0.2542 11.00000 0.05 0.14 Q12 1 0.4445 -0.0304 0.7447 11.00000 0.05 0.14 Q13 1 0.4511 -0.1135 0.5765 11.00000 0.05 0.14 Q14 1 0.3333 0.0045 0.5052 11.00000 0.05 0.14 Q15 1 0.5000 0.0000 1.0000 10.50000 0.05 0.14 Q16 1 0.3569 0.2122 0.3839 11.00000 0.05 0.14 Q17 1 0.7536 0.1572 0.8410 11.00000 0.05 0.13 Q18 1 0.5633 -0.1652 0.8619 11.00000 0.05 0.13 Q19 1 0.3222 0.0274 0.9978 11.00000 0.05 0.13 Q20 1 0.4355 0.1605 0.8456 11.00000 0.05 0.13 ; _shelx_res_checksum 2381 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 O1 O 0.1204(2) 0.02503(9) 0.28339(17) 0.0639(7) Uani 1 1 d . . . . . C1 C 0.2270(3) -0.02055(13) 0.5045(3) 0.0524(8) Uani 1 1 d . . . . . C6 C 0.2364(4) -0.08083(13) 0.5922(3) 0.0531(9) Uani 1 1 d . . . . . C5 C 0.1261(4) -0.02980(17) 0.3687(3) 0.0606(9) Uani 1 1 d . . . . . C4 C 0.2130(4) 0.08557(15) 0.3244(4) 0.0588(9) Uani 1 1 d . . . . . C3 C 0.3054(4) 0.09431(14) 0.4489(3) 0.0602(9) Uani 1 1 d . . . . . H3 H 0.366361 0.135724 0.475101 0.072 Uiso 1 1 calc R U . . . C2 C 0.3136(3) 0.04184(14) 0.5433(3) 0.0521(8) Uani 1 1 d . . . . . O2 O 0.0444(2) -0.08174(11) 0.31744(19) 0.0799(8) Uani 1 1 d . . . . . C9 C 0.2550(5) -0.19543(15) 0.7618(3) 0.0681(10) Uani 1 1 d . . . . . C8 C 0.1136(4) -0.17216(15) 0.6675(3) 0.0711(10) Uani 1 1 d . . . . . H8 H 0.023051 -0.195068 0.660837 0.085 Uiso 1 1 calc R U . . . C7 C 0.1021(3) -0.11644(14) 0.5833(3) 0.0629(9) Uani 1 1 d . . . . . H7 H 0.005425 -0.102672 0.520849 0.075 Uiso 1 1 calc R U . . . C16 C 0.6192(5) 0.09050(17) 0.9342(4) 0.0924(12) Uani 1 1 d . . . . . H16 H 0.686141 0.099901 1.019773 0.111 Uiso 1 1 calc R U . . . C15 C 0.4643(5) 0.07499(17) 0.9011(4) 0.0857(12) Uani 1 1 d . . . . . H15 H 0.426698 0.075854 0.964772 0.103 Uiso 1 1 calc R U . . . C14 C 0.3648(4) 0.05831(14) 0.7761(4) 0.0685(10) Uani 1 1 d . . . . . H14 H 0.261589 0.046873 0.756101 0.082 Uiso 1 1 calc R U . . . C13 C 0.4186(4) 0.05860(13) 0.6804(3) 0.0556(9) Uani 1 1 d . . . . . C12 C 0.2652(4) -0.25614(15) 0.8530(3) 0.1079(14) Uani 1 1 d . . . . . H12A H 0.343847 -0.289771 0.855775 0.162 Uiso 1 1 calc R U . . . H12B H 0.166787 -0.280428 0.823411 0.162 Uiso 1 1 calc R U . . . H12C H 0.291538 -0.236953 0.937956 0.162 Uiso 1 1 calc R U . . . C11 C 0.3794(4) -0.10513(15) 0.6857(3) 0.0615(9) Uani 1 1 d . . . . . H11 H 0.470664 -0.083159 0.692012 0.074 Uiso 1 1 calc R U . . . C10 C 0.3873(4) -0.16057(15) 0.7681(3) 0.0698(10) Uani 1 1 d . . . . . H10 H 0.483823 -0.175106 0.829616 0.084 Uiso 1 1 calc R U . . . C18 C 0.5722(4) 0.07688(15) 0.7140(4) 0.0688(10) Uani 1 1 d . . . . . H18 H 0.608783 0.079142 0.649838 0.083 Uiso 1 1 calc R U . . . C17 C 0.6726(5) 0.09185(17) 0.8399(4) 0.0833(11) Uani 1 1 d . . . . . H17 H 0.776159 0.102795 0.860374 0.100 Uiso 1 1 calc R U . . . C20 C 0.2396(4) 0.20561(16) 0.2410(3) 0.0774(10) Uani 1 1 d . . . . . H20 H 0.278377 0.223476 0.324997 0.093 Uiso 1 1 calc R U . . . C19 C 0.1931(3) 0.13427(16) 0.2172(3) 0.0604(9) Uani 1 1 d . . . . . C21 C 0.2287(4) 0.25044(17) 0.1407(4) 0.0893(12) Uani 1 1 d . . . . . H21 H 0.261174 0.298273 0.157392 0.107 Uiso 1 1 calc R U . . . C24 C 0.1341(4) 0.10901(18) 0.0916(4) 0.0812(11) Uani 1 1 d . . . . . H24 H 0.101466 0.061244 0.074139 0.097 Uiso 1 1 calc R U . . . C23 C 0.1234(4) 0.1545(2) -0.0086(3) 0.0930(12) Uani 1 1 d . . . . . H23 H 0.084292 0.137185 -0.092950 0.112 Uiso 1 1 calc R U . . . C22 C 0.1706(4) 0.2249(2) 0.0169(4) 0.0944(13) Uani 1 1 d . . . . . H22 H 0.163012 0.255444 -0.050348 0.113 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 O1 0.0737(16) 0.0628(13) 0.0535(16) 0.0058(10) 0.0248(13) -0.0015(11) C1 0.057(2) 0.0552(17) 0.046(2) 0.0003(16) 0.0234(18) 0.0006(15) C6 0.058(2) 0.0498(17) 0.055(2) -0.0051(15) 0.027(2) 0.0018(15) C5 0.067(2) 0.062(2) 0.057(3) 0.0031(19) 0.031(2) 0.0030(17) C4 0.070(2) 0.0570(19) 0.060(2) -0.0010(18) 0.037(2) -0.0003(16) C3 0.077(2) 0.0544(17) 0.057(2) 0.0016(18) 0.035(2) -0.0051(16) C2 0.055(2) 0.0565(17) 0.047(2) -0.0003(16) 0.0236(19) 0.0041(15) O2 0.0967(19) 0.0680(14) 0.0678(19) -0.0090(11) 0.0271(16) -0.0186(12) C9 0.098(3) 0.0521(19) 0.057(3) -0.0005(16) 0.035(2) 0.0021(19) C8 0.086(3) 0.064(2) 0.075(3) -0.0004(19) 0.045(2) -0.0101(18) C7 0.063(2) 0.0587(18) 0.072(2) 0.0005(17) 0.0330(19) 0.0015(16) C16 0.119(4) 0.088(3) 0.064(3) -0.015(2) 0.032(3) -0.007(2) C15 0.126(4) 0.080(2) 0.068(3) -0.008(2) 0.057(3) -0.003(2) C14 0.091(3) 0.066(2) 0.062(3) -0.0052(18) 0.046(2) -0.0037(18) C13 0.075(2) 0.0446(16) 0.051(2) 0.0004(15) 0.030(2) 0.0009(15) C12 0.167(4) 0.067(2) 0.088(3) 0.016(2) 0.051(3) -0.015(2) C11 0.067(2) 0.0548(18) 0.067(3) -0.0013(16) 0.032(2) 0.0044(16) C10 0.087(3) 0.0553(18) 0.065(3) 0.0017(17) 0.030(2) 0.0082(18) C18 0.076(3) 0.074(2) 0.062(3) -0.0104(18) 0.035(2) -0.0107(18) C17 0.077(3) 0.095(3) 0.070(3) -0.015(2) 0.024(3) -0.0173(19) C20 0.105(3) 0.066(2) 0.071(3) 0.0119(19) 0.047(2) 0.0092(19) C19 0.069(2) 0.068(2) 0.051(2) 0.0090(18) 0.031(2) 0.0071(16) C21 0.120(3) 0.070(2) 0.093(3) 0.021(2) 0.060(3) 0.015(2) C24 0.093(3) 0.088(2) 0.068(3) 0.010(2) 0.039(2) -0.007(2) C23 0.101(3) 0.118(3) 0.059(3) 0.011(3) 0.033(2) -0.005(2) C22 0.108(3) 0.099(3) 0.091(4) 0.033(3) 0.056(3) 0.013(2) 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 C4 O1 C5 121.5(3) . . ? C2 C1 C5 118.7(3) . . ? C2 C1 C6 123.8(3) . . ? C5 C1 C6 117.4(3) . . ? C7 C6 C11 117.7(3) . . ? C7 C6 C1 120.7(3) . . ? C11 C6 C1 121.6(3) . . ? O2 C5 O1 114.1(3) . . ? O2 C5 C1 127.5(3) . . ? O1 C5 C1 118.4(3) . . ? C3 C4 O1 120.2(3) . . ? C3 C4 C19 127.8(3) . . ? O1 C4 C19 112.0(3) . . ? C4 C3 C2 121.7(3) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C1 C2 C3 119.4(3) . . ? C1 C2 C13 123.9(3) . . ? C3 C2 C13 116.7(3) . . ? C10 C9 C8 117.1(3) . . ? C10 C9 C12 121.0(3) . . ? C8 C9 C12 121.9(3) . . ? C7 C8 C9 122.6(3) . . ? C7 C8 H8 118.7 . . ? C9 C8 H8 118.7 . . ? C8 C7 C6 119.7(3) . . ? C8 C7 H7 120.2 . . ? C6 C7 H7 120.2 . . ? C17 C16 C15 119.1(4) . . ? C17 C16 H16 120.4 . . ? C15 C16 H16 120.4 . . ? C14 C15 C16 121.4(3) . . ? C14 C15 H15 119.3 . . ? C16 C15 H15 119.3 . . ? C15 C14 C13 119.8(3) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C14 C13 C18 118.2(3) . . ? C14 C13 C2 121.3(3) . . ? C18 C13 C2 120.5(3) . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C10 C11 C6 121.3(3) . . ? C10 C11 H11 119.3 . . ? C6 C11 H11 119.3 . . ? C11 C10 C9 121.5(3) . . ? C11 C10 H10 119.2 . . ? C9 C10 H10 119.2 . . ? C17 C18 C13 121.9(3) . . ? C17 C18 H18 119.0 . . ? C13 C18 H18 119.0 . . ? C16 C17 C18 119.6(4) . . ? C16 C17 H17 120.2 . . ? C18 C17 H17 120.2 . . ? C21 C20 C19 120.3(3) . . ? C21 C20 H20 119.9 . . ? C19 C20 H20 119.9 . . ? C24 C19 C20 119.0(3) . . ? C24 C19 C4 120.7(3) . . ? C20 C19 C4 120.3(3) . . ? C22 C21 C20 120.3(3) . . ? C22 C21 H21 119.9 . . ? C20 C21 H21 119.9 . . ? C19 C24 C23 120.3(3) . . ? C19 C24 H24 119.8 . . ? C23 C24 H24 119.8 . . ? C22 C23 C24 119.9(4) . . ? C22 C23 H23 120.1 . . ? C24 C23 H23 120.1 . . ? C21 C22 C23 120.3(4) . . ? C21 C22 H22 119.8 . . ? C23 C22 H22 119.8 . . ? 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 O1 C4 1.378(3) . ? O1 C5 1.389(3) . ? C1 C2 1.378(3) . ? C1 C5 1.449(4) . ? C1 C6 1.474(3) . ? C6 C7 1.397(4) . ? C6 C11 1.402(4) . ? C5 O2 1.219(3) . ? C4 C3 1.329(4) . ? C4 C19 1.464(4) . ? C3 C2 1.425(3) . ? C3 H3 0.9300 . ? C2 C13 1.492(4) . ? C9 C10 1.382(4) . ? C9 C8 1.390(4) . ? C9 C12 1.504(4) . ? C8 C7 1.380(4) . ? C8 H8 0.9300 . ? C7 H7 0.9300 . ? C16 C17 1.362(5) . ? C16 C15 1.383(5) . ? C16 H16 0.9300 . ? C15 C14 1.375(4) . ? C15 H15 0.9300 . ? C14 C13 1.381(4) . ? C14 H14 0.9300 . ? C13 C18 1.381(4) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C11 C10 1.370(4) . ? C11 H11 0.9300 . ? C10 H10 0.9300 . ? C18 C17 1.377(4) . ? C18 H18 0.9300 . ? C17 H17 0.9300 . ? C20 C21 1.379(4) . ? C20 C19 1.382(4) . ? C20 H20 0.9300 . ? C19 C24 1.381(4) . ? C21 C22 1.364(4) . ? C21 H21 0.9300 . ? C24 C23 1.385(4) . ? C24 H24 0.9300 . ? C23 C22 1.368(4) . ? C23 H23 0.9300 . ? C22 H22 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 C2 C1 C6 C7 138.7(3) . . . . ? C5 C1 C6 C7 -44.6(3) . . . . ? C2 C1 C6 C11 -42.3(4) . . . . ? C5 C1 C6 C11 134.5(3) . . . . ? C4 O1 C5 O2 -175.9(2) . . . . ? C4 O1 C5 C1 2.9(3) . . . . ? C2 C1 C5 O2 178.3(3) . . . . ? C6 C1 C5 O2 1.4(4) . . . . ? C2 C1 C5 O1 -0.4(4) . . . . ? C6 C1 C5 O1 -177.3(2) . . . . ? C5 O1 C4 C3 -3.1(4) . . . . ? C5 O1 C4 C19 177.2(2) . . . . ? O1 C4 C3 C2 0.7(4) . . . . ? C19 C4 C3 C2 -179.7(3) . . . . ? C5 C1 C2 C3 -1.9(4) . . . . ? C6 C1 C2 C3 174.8(2) . . . . ? C5 C1 C2 C13 178.4(2) . . . . ? C6 C1 C2 C13 -4.9(4) . . . . ? C4 C3 C2 C1 1.8(4) . . . . ? C4 C3 C2 C13 -178.5(3) . . . . ? C10 C9 C8 C7 -0.6(5) . . . . ? C12 C9 C8 C7 179.8(3) . . . . ? C9 C8 C7 C6 -0.6(4) . . . . ? C11 C6 C7 C8 1.7(4) . . . . ? C1 C6 C7 C8 -179.2(2) . . . . ? C17 C16 C15 C14 2.4(5) . . . . ? C16 C15 C14 C13 -1.6(5) . . . . ? C15 C14 C13 C18 -0.9(4) . . . . ? C15 C14 C13 C2 -179.1(2) . . . . ? C1 C2 C13 C14 -55.1(4) . . . . ? C3 C2 C13 C14 125.3(3) . . . . ? C1 C2 C13 C18 126.7(3) . . . . ? C3 C2 C13 C18 -52.9(3) . . . . ? C7 C6 C11 C10 -1.8(4) . . . . ? C1 C6 C11 C10 179.2(2) . . . . ? C6 C11 C10 C9 0.6(4) . . . . ? C8 C9 C10 C11 0.5(4) . . . . ? C12 C9 C10 C11 -179.8(3) . . . . ? C14 C13 C18 C17 2.5(4) . . . . ? C2 C13 C18 C17 -179.2(3) . . . . ? C15 C16 C17 C18 -0.8(5) . . . . ? C13 C18 C17 C16 -1.7(5) . . . . ? C21 C20 C19 C24 -0.7(4) . . . . ? C21 C20 C19 C4 176.4(3) . . . . ? C3 C4 C19 C24 158.9(3) . . . . ? O1 C4 C19 C24 -21.4(4) . . . . ? C3 C4 C19 C20 -18.1(4) . . . . ? O1 C4 C19 C20 161.5(2) . . . . ? C19 C20 C21 C22 0.6(5) . . . . ? C20 C19 C24 C23 0.6(5) . . . . ? C4 C19 C24 C23 -176.5(3) . . . . ? C19 C24 C23 C22 -0.4(5) . . . . ? C20 C21 C22 C23 -0.4(5) . . . . ? C24 C23 C22 C21 0.3(5) . . . . ?