#------------------------------------------------------------------------------ #$Date: 2023-02-03 04:11:54 +0200 (Fri, 03 Feb 2023) $ #$Revision: 280776 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/62/7246237.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_7246237 loop_ _publ_author_name 'Ali, Akbar' 'Din, Zia Ud' 'Ibrahim, Muhammad' 'Ashfaq, Muhammad' 'Muhammad, Shabbir' 'Gull, Dania' 'Tahir, Muhammad Nawaz' 'Rodrigues-Filho, Edson' 'Al-Sehemi, Abdullah G.' 'Suleman, Muhammad' _publ_section_title ; Acid catalyzed one-pot approach towards the synthesis of curcuminoid systems: unsymmetrical diarylidene cycloalkanones, exploration of their single crystals, optical and nonlinear optical properties ; _journal_issue 7 _journal_name_full 'RSC Advances' _journal_page_first 4476 _journal_page_last 4494 _journal_paper_doi 10.1039/D2RA07681K _journal_volume 13 _journal_year 2023 _chemical_formula_iupac 'C21 H20 O3' _chemical_formula_moiety 'C21 H20 O3' _chemical_formula_sum 'C21 H20 O3' _chemical_formula_weight 320.37 _chemical_name_systematic ; (2E,5E)-2-benzylidene-5-(2,3-dimethoxybenzylidene)cyclopentanone ; _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_Hall '-P 2ac 2ab' _space_group_name_H-M_alt 'P b c a' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2019/2 _audit_update_record ; 2022-05-11 deposited with the CCDC. 2023-01-12 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 16.154(2) _cell_length_b 6.9813(10) _cell_length_c 28.997(4) _cell_measurement_reflns_used 2623 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 25.347 _cell_measurement_theta_min 1.404 _cell_volume 3270.2(8) _computing_cell_refinement 'SAINT (Bruker, 2007)' _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_data_reduction 'SAINT (Bruker, 2007)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009)' _computing_publication_material ; WinGX (Farrugia, 2012) and PLATON (Spek, 2009) ; _computing_structure_refinement 'SHELXL-2019/2 (Sheldrick, 2019)' _computing_structure_solution 'SHELXT-2015 (Sheldrick, 2015)' _diffrn_ambient_temperature 150(2) _diffrn_detector_area_resol_mean 8.301 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker Kappa APEXII CCD' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_unetI/netI 0.0108 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_number 57033 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.347 _diffrn_reflns_theta_min 1.404 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_T_max 0.988 _exptl_absorpt_correction_T_min 0.983 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2007)' _exptl_crystal_colour white _exptl_crystal_density_diffrn 1.301 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 1360 _exptl_crystal_size_max 0.361 _exptl_crystal_size_mid 0.345 _exptl_crystal_size_min 0.194 _refine_diff_density_max 0.215 _refine_diff_density_min -0.174 _refine_diff_density_rms 0.042 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.159 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 219 _refine_ls_number_reflns 2992 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.159 _refine_ls_R_factor_all 0.0623 _refine_ls_R_factor_gt 0.0547 _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^)+(0.0146P)^2^+4.2071P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1123 _refine_ls_wR_factor_ref 0.1161 _reflns_number_gt 2623 _reflns_number_total 2992 _reflns_threshold_expression I>2\s(I) _cod_data_source_file d2ra07681k2.cif _cod_data_source_block A1K10A10 _cod_database_code 7246237 _shelx_shelxl_version_number 2019/2 _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 ; shelx.res created by SHELXL-2014/7 TITL A1K10A10 in Pbca CELL 0.71073 16.1540 6.9813 28.9971 90.000 90.000 90.000 ZERR 8.00 0.0023 0.0010 0.0042 0.000 0.000 0.000 LATT 1 SYMM 1/2 + X, 1/2 - Y, - Z SYMM - X, 1/2 + Y, 1/2 - Z SYMM 1/2 - X, - Y, 1/2 + Z SFAC C H O UNIT 168 160 24 ACTA L.S. 40 MERG 2 FMAP 2 PLAN 6 SHEL 999 0.83 SIZE 0.048 0.403 0.575 BOND $H HTAB CONF LIST 4 TEMP -123.15 EQIV_$1 -X, -Y, -Z HTAB C14 O3_$1 EQIV_$2 -X, -Y-1, -Z HTAB C17 O3_$2 WGHT 0.014600 4.207100 FVAR 0.07230 O1 3 0.104091 0.107214 0.169556 11.00000 0.04409 0.02855 = 0.04989 0.01196 0.00111 0.00243 O2 3 0.145321 0.421561 0.216172 11.00000 0.05058 0.04139 = 0.05469 0.00031 -0.01105 -0.00367 O3 3 0.026059 -0.241634 0.032330 11.00000 0.03875 0.04490 = 0.04482 0.01295 0.00156 -0.01466 C1 1 0.126535 0.264916 0.096826 11.00000 0.02747 0.02854 = 0.05242 0.00858 -0.00005 -0.00008 C2 1 0.124977 0.270954 0.144808 11.00000 0.02627 0.02756 = 0.05311 0.01162 -0.00176 0.00184 C3 1 0.148090 0.435221 0.168966 11.00000 0.02714 0.03759 = 0.05172 0.00582 -0.00674 0.00141 C4 1 0.172012 0.597357 0.144786 11.00000 0.02833 0.03144 = 0.06960 0.00290 -0.00590 -0.00507 AFIX 43 H4 2 0.187300 0.710390 0.160917 11.00000 -1.20000 AFIX 0 C5 1 0.173546 0.594012 0.097107 11.00000 0.03093 0.03159 = 0.06611 0.01449 0.00004 -0.00541 AFIX 43 H5 2 0.190184 0.705217 0.080657 11.00000 -1.20000 AFIX 0 C6 1 0.151356 0.432195 0.073232 11.00000 0.03385 0.03393 = 0.05682 0.01414 0.00164 -0.00186 AFIX 43 H6 2 0.152717 0.432780 0.040479 11.00000 -1.20000 AFIX 0 C7 1 0.023819 0.117705 0.190198 11.00000 0.04603 0.03705 = 0.05575 0.01281 0.00041 -0.00576 AFIX 137 H7A 2 0.017146 0.012165 0.212169 11.00000 -1.50000 H7B 2 -0.018631 0.108005 0.166167 11.00000 -1.50000 H7C 2 0.017933 0.240134 0.206404 11.00000 -1.50000 AFIX 0 C8 1 0.160354 0.593422 0.241289 11.00000 0.05309 0.05339 = 0.06402 -0.00730 -0.01948 -0.00583 AFIX 137 H8A 2 0.153792 0.568677 0.274355 11.00000 -1.50000 H8B 2 0.120773 0.691915 0.231609 11.00000 -1.50000 H8C 2 0.216838 0.637914 0.235183 11.00000 -1.50000 AFIX 0 C9 1 0.100129 0.091340 0.072683 11.00000 0.03013 0.03052 = 0.05031 0.01456 -0.00030 -0.00099 AFIX 43 H9 2 0.069649 0.002571 0.090801 11.00000 -1.20000 AFIX 0 C10 1 0.112603 0.039406 0.028894 11.00000 0.02899 0.03340 = 0.04347 0.01538 -0.00207 -0.00202 C11 1 0.077007 -0.142200 0.011665 11.00000 0.02593 0.03743 = 0.04358 0.01730 -0.00713 -0.00336 C12 1 0.111605 -0.183148 -0.034589 11.00000 0.02647 0.03702 = 0.04128 0.01804 -0.00474 -0.00379 C13 1 0.169686 -0.022333 -0.047775 11.00000 0.03305 0.03868 = 0.04256 0.01813 -0.00288 -0.00544 AFIX 23 H13A 2 0.153779 0.032515 -0.077987 11.00000 -1.20000 H13B 2 0.227306 -0.069860 -0.049847 11.00000 -1.20000 AFIX 0 C14 1 0.162037 0.130285 -0.009390 11.00000 0.03548 0.03578 = 0.04820 0.01518 -0.00174 -0.00624 AFIX 23 H14A 2 0.217527 0.168197 0.001868 11.00000 -1.20000 H14B 2 0.133391 0.245669 -0.021189 11.00000 -1.20000 AFIX 0 C15 1 0.087358 -0.340209 -0.057731 11.00000 0.02834 0.03836 = 0.04376 0.01873 -0.00264 -0.00426 AFIX 43 H15 2 0.049865 -0.420308 -0.041447 11.00000 -1.20000 AFIX 0 C16 1 0.109108 -0.407757 -0.103653 11.00000 0.02918 0.03281 = 0.04126 0.01549 -0.00357 -0.00012 C17 1 0.060353 -0.551384 -0.123419 11.00000 0.03350 0.03498 = 0.05385 0.01107 0.00284 -0.00534 AFIX 43 H17 2 0.016082 -0.605165 -0.106173 11.00000 -1.20000 AFIX 0 C18 1 0.075453 -0.616255 -0.167519 11.00000 0.04056 0.03829 = 0.06113 0.00058 0.00263 -0.00212 AFIX 43 H18 2 0.040419 -0.711158 -0.180571 11.00000 -1.20000 AFIX 0 C19 1 0.140727 -0.545249 -0.192943 11.00000 0.04225 0.03445 = 0.05828 0.00190 0.00578 0.00784 AFIX 43 H19 2 0.150938 -0.590564 -0.223307 11.00000 -1.20000 AFIX 0 C20 1 0.191143 -0.406749 -0.173457 11.00000 0.03543 0.03703 = 0.05505 0.01056 0.00775 0.00363 AFIX 43 H20 2 0.236868 -0.358605 -0.190490 11.00000 -1.20000 AFIX 0 C21 1 0.176103 -0.338006 -0.129960 11.00000 0.03153 0.03274 = 0.04972 0.01113 -0.00295 -0.00196 AFIX 43 H21 2 0.211238 -0.242204 -0.117381 11.00000 -1.20000 AFIX 0 HKLF 4 1.0 1.00 0.00 0.00 0.00 1.00 0.00 0.00 0.00 1.00 REM A1K10A10 in Pbca REM R1 = 0.0547 for 2623 Fo > 4sig(Fo) and 0.0623 for all 2992 data REM 219 parameters refined using 0 restraints END WGHT 0.0142 4.2143 REM Instructions for potential hydrogen bonds HTAB C7 O2 REM Highest difference peak 0.215, deepest hole -0.174, 1-sigma level 0.042 Q1 1 0.1375 0.0313 0.0511 11.00000 0.05 0.22 Q2 1 0.0701 -0.1206 -0.0181 11.00000 0.05 0.21 Q3 1 0.1054 -0.6358 -0.1378 11.00000 0.05 0.20 Q4 1 0.1557 0.2454 0.1207 11.00000 0.05 0.20 Q5 1 0.1607 -0.3070 -0.1582 11.00000 0.05 0.18 Q6 1 0.0794 -0.3292 -0.0893 11.00000 0.05 0.18 ; _shelx_res_checksum 34769 loop_ _space_group_symop_operation_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -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 0.10409(10) 0.1072(2) 0.16956(6) 0.0408(4) Uani 1 1 d . . . . . O2 O 0.14532(11) 0.4216(3) 0.21617(6) 0.0489(5) Uani 1 1 d . . . . . O3 O 0.02606(10) -0.2416(3) 0.03233(6) 0.0428(4) Uani 1 1 d . . . . . C1 C 0.12653(14) 0.2649(3) 0.09683(9) 0.0361(5) Uani 1 1 d . . . . . C2 C 0.12498(14) 0.2710(3) 0.14481(9) 0.0356(5) Uani 1 1 d . . . . . C3 C 0.14809(14) 0.4352(4) 0.16897(9) 0.0388(6) Uani 1 1 d . . . . . C4 C 0.17201(14) 0.5974(4) 0.14479(10) 0.0431(6) Uani 1 1 d . . . . . H4 H 0.1873 0.7104 0.1609 0.052 Uiso 1 1 calc R U . . . C5 C 0.17355(14) 0.5940(3) 0.09711(10) 0.0429(6) Uani 1 1 d . . . . . H5 H 0.1902 0.7052 0.0807 0.051 Uiso 1 1 calc R U . . . C6 C 0.15136(14) 0.4322(3) 0.07323(10) 0.0415(6) Uani 1 1 d . . . . . H6 H 0.1527 0.4328 0.0405 0.050 Uiso 1 1 calc R U . . . C7 C 0.02382(16) 0.1177(4) 0.19020(9) 0.0463(6) Uani 1 1 d . . . . . H7A H 0.0171 0.0122 0.2122 0.069 Uiso 1 1 calc R U . . . H7B H -0.0186 0.1080 0.1662 0.069 Uiso 1 1 calc R U . . . H7C H 0.0179 0.2401 0.2064 0.069 Uiso 1 1 calc R U . . . C8 C 0.16035(18) 0.5934(4) 0.24129(10) 0.0568(8) Uani 1 1 d . . . . . H8A H 0.1538 0.5687 0.2744 0.085 Uiso 1 1 calc R U . . . H8B H 0.1208 0.6919 0.2316 0.085 Uiso 1 1 calc R U . . . H8C H 0.2168 0.6379 0.2352 0.085 Uiso 1 1 calc R U . . . C9 C 0.10013(14) 0.0913(3) 0.07268(9) 0.0370(6) Uani 1 1 d . . . . . H9 H 0.0696 0.0026 0.0908 0.044 Uiso 1 1 calc R U . . . C10 C 0.11260(14) 0.0394(3) 0.02889(8) 0.0353(5) Uani 1 1 d . . . . . C11 C 0.07701(13) -0.1422(3) 0.01166(8) 0.0356(6) Uani 1 1 d . . . . . C12 C 0.11160(13) -0.1831(3) -0.03459(8) 0.0349(5) Uani 1 1 d . . . . . C13 C 0.16969(14) -0.0223(3) -0.04778(8) 0.0381(6) Uani 1 1 d . . . . . H13A H 0.1538 0.0325 -0.0780 0.046 Uiso 1 1 calc R U . . . H13B H 0.2273 -0.0699 -0.0498 0.046 Uiso 1 1 calc R U . . . C14 C 0.16204(15) 0.1303(3) -0.00939(8) 0.0398(6) Uani 1 1 d . . . . . H14A H 0.2175 0.1682 0.0019 0.048 Uiso 1 1 calc R U . . . H14B H 0.1334 0.2457 -0.0212 0.048 Uiso 1 1 calc R U . . . C15 C 0.08736(14) -0.3402(3) -0.05773(8) 0.0368(6) Uani 1 1 d . . . . . H15 H 0.0499 -0.4203 -0.0414 0.044 Uiso 1 1 calc R U . . . C16 C 0.10911(14) -0.4078(3) -0.10365(8) 0.0344(5) Uani 1 1 d . . . . . C17 C 0.06035(15) -0.5514(3) -0.12342(9) 0.0408(6) Uani 1 1 d . . . . . H17 H 0.0161 -0.6052 -0.1062 0.049 Uiso 1 1 calc R U . . . C18 C 0.07545(16) -0.6163(4) -0.16752(10) 0.0467(7) Uani 1 1 d . . . . . H18 H 0.0404 -0.7112 -0.1806 0.056 Uiso 1 1 calc R U . . . C19 C 0.14073(16) -0.5452(4) -0.19294(10) 0.0450(6) Uani 1 1 d . . . . . H19 H 0.1509 -0.5906 -0.2233 0.054 Uiso 1 1 calc R U . . . C20 C 0.19114(15) -0.4067(4) -0.17346(9) 0.0425(6) Uani 1 1 d . . . . . H20 H 0.2369 -0.3586 -0.1905 0.051 Uiso 1 1 calc R U . . . C21 C 0.17610(14) -0.3380(3) -0.12996(9) 0.0380(6) Uani 1 1 d . . . . . H21 H 0.2112 -0.2422 -0.1174 0.046 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 0.0441(10) 0.0286(8) 0.0499(10) 0.0120(8) 0.0011(8) 0.0024(7) O2 0.0506(11) 0.0414(10) 0.0547(11) 0.0003(9) -0.0110(9) -0.0037(9) O3 0.0387(9) 0.0449(10) 0.0448(10) 0.0129(8) 0.0016(8) -0.0147(8) C1 0.0275(11) 0.0285(12) 0.0524(15) 0.0086(11) 0.0000(11) -0.0001(10) C2 0.0263(11) 0.0276(11) 0.0531(15) 0.0116(11) -0.0018(11) 0.0018(10) C3 0.0271(12) 0.0376(13) 0.0517(15) 0.0058(12) -0.0067(11) 0.0014(10) C4 0.0283(12) 0.0314(13) 0.0696(19) 0.0029(13) -0.0059(12) -0.0051(10) C5 0.0309(13) 0.0316(13) 0.0661(18) 0.0145(12) 0.0000(12) -0.0054(10) C6 0.0339(13) 0.0339(13) 0.0568(16) 0.0141(12) 0.0016(12) -0.0019(11) C7 0.0460(15) 0.0371(13) 0.0558(16) 0.0128(12) 0.0004(13) -0.0058(12) C8 0.0531(17) 0.0534(17) 0.0640(19) -0.0073(15) -0.0195(15) -0.0058(14) C9 0.0301(12) 0.0305(12) 0.0503(15) 0.0146(11) -0.0003(11) -0.0010(10) C10 0.0290(12) 0.0334(12) 0.0435(14) 0.0154(11) -0.0021(10) -0.0020(10) C11 0.0259(11) 0.0374(13) 0.0436(14) 0.0173(11) -0.0071(10) -0.0034(10) C12 0.0265(11) 0.0370(13) 0.0413(13) 0.0180(11) -0.0047(10) -0.0038(10) C13 0.0330(12) 0.0387(13) 0.0426(14) 0.0181(11) -0.0029(11) -0.0054(11) C14 0.0355(13) 0.0358(13) 0.0482(15) 0.0152(11) -0.0017(11) -0.0062(11) C15 0.0283(11) 0.0384(13) 0.0438(14) 0.0187(11) -0.0026(10) -0.0043(10) C16 0.0292(11) 0.0328(12) 0.0413(13) 0.0155(10) -0.0036(10) -0.0001(10) C17 0.0335(12) 0.0350(13) 0.0539(16) 0.0111(12) 0.0028(12) -0.0053(11) C18 0.0406(14) 0.0383(14) 0.0611(18) 0.0006(13) 0.0026(13) -0.0021(11) C19 0.0423(14) 0.0345(13) 0.0583(17) 0.0019(12) 0.0058(13) 0.0078(11) C20 0.0354(13) 0.0370(13) 0.0551(16) 0.0106(12) 0.0078(12) 0.0036(11) C21 0.0315(12) 0.0327(12) 0.0497(15) 0.0111(11) -0.0029(11) -0.0020(10) 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' 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 C7 113.19(18) . . ? C3 O2 C8 116.5(2) . . ? C2 C1 C6 117.7(2) . . ? C2 C1 C9 119.9(2) . . ? C6 C1 C9 122.4(2) . . ? O1 C2 C1 119.7(2) . . ? O1 C2 C3 118.8(2) . . ? C1 C2 C3 121.5(2) . . ? O2 C3 C4 124.8(2) . . ? O2 C3 C2 115.8(2) . . ? C4 C3 C2 119.5(2) . . ? C5 C4 C3 119.8(2) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C6 C5 C4 120.9(2) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C1 120.7(2) . . ? C5 C6 H6 119.6 . . ? C1 C6 H6 119.6 . . ? O1 C7 H7A 109.5 . . ? O1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? O1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O2 C8 H8A 109.5 . . ? O2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C1 129.5(2) . . ? C10 C9 H9 115.3 . . ? C1 C9 H9 115.3 . . ? C9 C10 C11 119.7(2) . . ? C9 C10 C14 131.7(2) . . ? C11 C10 C14 108.5(2) . . ? O3 C11 C10 125.3(2) . . ? O3 C11 C12 125.7(2) . . ? C10 C11 C12 108.95(19) . . ? C15 C12 C11 120.0(2) . . ? C15 C12 C13 131.3(2) . . ? C11 C12 C13 108.7(2) . . ? C12 C13 C14 106.26(19) . . ? C12 C13 H13A 110.5 . . ? C14 C13 H13A 110.5 . . ? C12 C13 H13B 110.5 . . ? C14 C13 H13B 110.5 . . ? H13A C13 H13B 108.7 . . ? C10 C14 C13 106.41(19) . . ? C10 C14 H14A 110.4 . . ? C13 C14 H14A 110.4 . . ? C10 C14 H14B 110.4 . . ? C13 C14 H14B 110.4 . . ? H14A C14 H14B 108.6 . . ? C12 C15 C16 130.6(2) . . ? C12 C15 H15 114.7 . . ? C16 C15 H15 114.7 . . ? C17 C16 C21 117.3(2) . . ? C17 C16 C15 118.1(2) . . ? C21 C16 C15 124.6(2) . . ? C18 C17 C16 121.1(2) . . ? C18 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? C17 C18 C19 120.9(3) . . ? C17 C18 H18 119.6 . . ? C19 C18 H18 119.6 . . ? C18 C19 C20 118.9(3) . . ? C18 C19 H19 120.6 . . ? C20 C19 H19 120.6 . . ? C21 C20 C19 121.0(2) . . ? C21 C20 H20 119.5 . . ? C19 C20 H20 119.5 . . ? C20 C21 C16 120.8(2) . . ? C20 C21 H21 119.6 . . ? C16 C21 H21 119.6 . . ? 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 C2 1.391(3) . ? O1 C7 1.430(3) . ? O2 C3 1.373(3) . ? O2 C8 1.424(3) . ? O3 C11 1.232(3) . ? C1 C2 1.392(3) . ? C1 C6 1.412(3) . ? C1 C9 1.463(3) . ? C2 C3 1.395(3) . ? C3 C4 1.386(3) . ? C4 C5 1.383(4) . ? C4 H4 0.9500 . ? C5 C6 1.373(4) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.336(3) . ? C9 H9 0.9500 . ? C10 C11 1.479(3) . ? C10 C14 1.508(3) . ? C11 C12 1.481(3) . ? C12 C15 1.344(3) . ? C12 C13 1.512(3) . ? C13 C14 1.546(4) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.456(3) . ? C15 H15 0.9500 . ? C16 C17 1.398(3) . ? C16 C21 1.411(3) . ? C17 C18 1.378(4) . ? C17 H17 0.9500 . ? C18 C19 1.379(4) . ? C18 H18 0.9500 . ? C19 C20 1.385(4) . ? C19 H19 0.9500 . ? C20 C21 1.371(4) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C14 H14B O3 0.99 2.60 3.206(3) 119.9 5 C17 H17 O3 0.95 2.49 3.319(3) 146.0 5_545 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 C7 O1 C2 C1 -107.6(2) . . . . ? C7 O1 C2 C3 75.7(3) . . . . ? C6 C1 C2 O1 -177.5(2) . . . . ? C9 C1 C2 O1 4.7(3) . . . . ? C6 C1 C2 C3 -0.8(3) . . . . ? C9 C1 C2 C3 -178.7(2) . . . . ? C8 O2 C3 C4 6.5(3) . . . . ? C8 O2 C3 C2 -173.7(2) . . . . ? O1 C2 C3 O2 -2.2(3) . . . . ? C1 C2 C3 O2 -178.8(2) . . . . ? O1 C2 C3 C4 177.6(2) . . . . ? C1 C2 C3 C4 1.0(4) . . . . ? O2 C3 C4 C5 179.1(2) . . . . ? C2 C3 C4 C5 -0.7(4) . . . . ? C3 C4 C5 C6 0.3(4) . . . . ? C4 C5 C6 C1 -0.1(4) . . . . ? C2 C1 C6 C5 0.4(3) . . . . ? C9 C1 C6 C5 178.2(2) . . . . ? C2 C1 C9 C10 -164.3(2) . . . . ? C6 C1 C9 C10 18.0(4) . . . . ? C1 C9 C10 C11 -177.9(2) . . . . ? C1 C9 C10 C14 5.1(4) . . . . ? C9 C10 C11 O3 10.7(3) . . . . ? C14 C10 C11 O3 -171.6(2) . . . . ? C9 C10 C11 C12 -170.1(2) . . . . ? C14 C10 C11 C12 7.6(2) . . . . ? O3 C11 C12 C15 0.2(3) . . . . ? C10 C11 C12 C15 -179.0(2) . . . . ? O3 C11 C12 C13 178.2(2) . . . . ? C10 C11 C12 C13 -1.0(2) . . . . ? C15 C12 C13 C14 171.9(2) . . . . ? C11 C12 C13 C14 -5.8(2) . . . . ? C9 C10 C14 C13 166.3(2) . . . . ? C11 C10 C14 C13 -11.0(2) . . . . ? C12 C13 C14 C10 10.2(2) . . . . ? C11 C12 C15 C16 177.3(2) . . . . ? C13 C12 C15 C16 -0.2(4) . . . . ? C12 C15 C16 C17 -165.2(2) . . . . ? C12 C15 C16 C21 14.6(4) . . . . ? C21 C16 C17 C18 -2.5(3) . . . . ? C15 C16 C17 C18 177.3(2) . . . . ? C16 C17 C18 C19 2.0(4) . . . . ? C17 C18 C19 C20 -0.1(4) . . . . ? C18 C19 C20 C21 -1.1(4) . . . . ? C19 C20 C21 C16 0.5(4) . . . . ? C17 C16 C21 C20 1.3(3) . . . . ? C15 C16 C21 C20 -178.5(2) . . . . ?