#------------------------------------------------------------------------------ #$Date: 2024-05-05 07:01:22 +0300 (Sun, 05 May 2024) $ #$Revision: 291688 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/98/7159880.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_7159880 loop_ _publ_author_name 'Manikandan, Balasubramaniyam' 'Thamotharan, Subbiah' 'Blacque, Olivier' 'Selva Ganesan, Subramaniapillai' _publ_section_title ; Deconstructive annulation mediated one-pot synthesis of xanthene derivatives. ; _journal_issue 16 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 3279 _journal_page_last 3286 _journal_paper_doi 10.1039/d4ob00093e _journal_volume 22 _journal_year 2024 _chemical_formula_moiety 'C26 H24 O3' _chemical_formula_sum 'C26 H24 O3' _chemical_formula_weight 384.45 _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 dual _audit_creation_date 2023-10-18 _audit_creation_method ; Olex2 1.5 (compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817) ; _audit_update_record ; 2023-11-13 deposited with the CCDC. 2024-04-01 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 93.5670(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.03740(10) _cell_length_b 12.74610(10) _cell_length_c 15.5693(2) _cell_measurement_reflns_used 17882 _cell_measurement_temperature 160.0(1) _cell_measurement_theta_max 79.5540 _cell_measurement_theta_min 4.4770 _cell_volume 1988.04(4) _computing_cell_refinement 'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)' _computing_data_collection 'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)' _computing_data_reduction 'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL (Sheldrick, 2015b)' _computing_structure_solution 'SHELXT (Sheldrick, 2015a)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 160.0(1) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.993 _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 2.00 32.00 0.50 0.28 -- 10.00 42.00-178.09 60 2 \w 43.00 69.00 0.50 1.13 -- 111.50 -77.00 -60.00 52 3 \w 53.00 105.00 0.50 1.13 -- 111.50 -77.00 0.00 104 4 \w 42.00 99.00 0.50 1.13 -- 111.50 -77.00 30.00 114 5 \w 42.00 79.00 0.50 1.13 -- 111.50 -77.00 120.00 74 6 \w 1.00 26.00 0.50 0.28 -- 10.00 45.00 133.00 50 7 \w -5.00 21.00 0.50 0.28 -- 6.00 51.00 43.26 52 8 \w 41.00 66.00 0.50 1.13 -- 111.50 -61.00 120.00 50 9 \w 77.00 103.00 0.50 1.13 -- 111.50 -77.00 150.00 52 10 \w 78.00 104.00 0.50 1.13 -- 111.50 -77.00 -60.00 52 11 \w 61.00 87.00 0.50 1.13 -- 111.50 -77.00-150.00 52 12 \w 46.00 72.00 0.50 1.13 -- 111.50 -77.00-180.00 52 13 \w 41.00 66.00 0.50 1.13 -- 111.50 -61.00-180.00 50 14 \w 44.00 71.00 0.50 1.13 -- 111.50 -61.00-150.00 54 15 \w -6.00 20.00 0.50 0.28 -- 50.11 -13.00-164.00 52 16 \w 41.00 70.00 0.50 1.13 -- 111.50 -61.00 30.00 58 17 \w 41.00 66.00 0.50 1.13 -- 111.50 -61.00 90.00 50 18 \w 82.00 108.00 0.50 1.13 -- 111.50 -82.00 -16.53 52 19 \w 86.00 111.00 0.50 1.13 -- 111.50-125.00 0.00 50 20 \w 88.00 126.00 0.50 1.13 -- 111.50-150.00 12.41 76 21 \w 75.00 101.00 0.50 1.13 -- 111.50-125.00 120.00 52 22 \w 48.00 73.00 0.50 1.13 -- 111.50-150.00 12.41 50 23 \w 50.00 105.00 0.50 1.13 -- 111.50 -95.00 90.00 110 24 \w 76.00 101.00 0.50 1.13 -- 111.50 -95.00 120.00 50 25 \w 54.00 81.00 0.50 1.13 -- 111.50 -86.00 167.82 54 26 \w 45.00 75.00 0.50 1.13 -- 111.50-125.00 0.00 60 27 \w 49.00 75.00 0.50 1.13 -- 111.50 -82.00 -16.53 52 28 \w 49.00 100.00 0.50 1.13 -- 111.50-125.00 -60.00 102 29 \w 52.00 78.00 0.50 1.13 -- 111.50 -95.00-180.00 52 30 \w -155.00-108.00 0.50 1.13 -- -90.00-125.00 -90.00 94 31 \w -159.00-134.00 0.50 1.13 -- -90.00-125.00 -30.00 50 32 \w -154.00-128.00 0.50 1.13 -- -90.00 -61.00 -30.00 52 33 \w -146.00-120.00 0.50 1.13 -- -90.00 -13.00-164.00 52 34 \w -121.00 -48.00 0.50 0.28 -- -50.11 -13.00-164.00 146 35 \w -26.00 -1.00 0.50 0.28 -- -10.00 -47.00-131.70 50 36 \w -47.00 -19.00 0.50 1.13 -- -90.00 45.00 0.00 56 37 \w -8.00 22.00 0.50 0.28 -- -50.11 13.00 6.00 60 38 \w 127.00 153.00 0.50 1.13 -- 111.50 77.00 60.00 52 39 \w 143.00 177.00 0.50 1.13 -- 111.50 77.00 120.00 68 40 \w 152.00 178.00 0.50 1.13 -- 111.50 77.00 150.00 52 41 \w 123.00 149.00 0.50 1.13 -- 111.50 30.00 90.00 52 42 \w 130.00 155.00 0.50 1.13 -- 111.50 61.00 0.00 50 43 \w 122.00 178.00 0.50 1.13 -- 111.50 45.00 30.00 112 44 \w 152.00 177.00 0.50 1.13 -- 111.50 30.00 90.00 50 45 \w 104.00 168.00 0.50 1.13 -- 111.50 13.00 6.00 128 46 \w 43.00 69.00 0.50 0.28 -- 50.11 13.00 6.00 52 47 \w 76.00 115.00 0.50 0.28 -- 50.11 13.00 6.00 78 48 \w 137.00 175.00 0.50 1.13 -- 111.50 45.00-150.00 76 49 \w 122.00 171.00 0.50 1.13 -- 111.50 45.00-180.00 98 50 \w 118.00 146.00 0.50 1.13 -- 111.50 125.00 -90.00 56 51 \w 110.00 147.00 0.50 1.13 -- 111.50 125.00-180.00 74 52 \w 153.00 178.00 0.50 1.13 -- 111.50 125.00 -90.00 50 53 \w 108.00 173.00 0.50 1.13 -- 111.50 125.00 30.00 130 ; _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 -0.1496585000 _diffrn_orient_matrix_UB_12 -0.0048066000 _diffrn_orient_matrix_UB_13 0.0164459000 _diffrn_orient_matrix_UB_21 0.0333846000 _diffrn_orient_matrix_UB_22 0.0211044000 _diffrn_orient_matrix_UB_23 0.0963985000 _diffrn_orient_matrix_UB_31 -0.0119983000 _diffrn_orient_matrix_UB_32 0.1188715000 _diffrn_orient_matrix_UB_33 -0.0164148000 _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 0.0192 _diffrn_reflns_av_unetI/netI 0.0151 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.993 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 24751 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.993 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 79.834 _diffrn_reflns_theta_min 4.487 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.657 _exptl_absorpt_correction_T_max 0.953 _exptl_absorpt_correction_T_min 0.907 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro 1.171.42.100a (Rigaku Oxford Diffraction, 2023) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.284 _exptl_crystal_description plate _exptl_crystal_F_000 816 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.09 _refine_diff_density_max 0.262 _refine_diff_density_min -0.164 _refine_diff_density_rms 0.034 _refine_ls_extinction_coef 0.00121(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL (Sheldrick, 2015b)' _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 266 _refine_ls_number_reflns 4301 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.056 _refine_ls_R_factor_all 0.0357 _refine_ls_R_factor_gt 0.0340 _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^)+(0.0355P)^2^+0.6163P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0845 _refine_ls_wR_factor_ref 0.0859 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4058 _reflns_number_total 4301 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ob00093e2.cif _cod_data_source_block tham1310 _cod_depositor_comments 'Adding full bibliography for 7159879--7159880.cif.' _cod_database_code 7159880 _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 0.943 _shelx_estimated_absorpt_t_min 0.880 _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: C7(H7) 2.b Secondary CH2 refined with riding coordinates: C2(H2A,H2B), C4(H4A,H4B) 2.c Aromatic/amide H refined with riding coordinates: C10(H10), C11(H11), C14(H14), C15(H15), C16(H16), C17(H17), C21(H21), C23(H23), C24(H24), C25(H25) 2.d Idealised Me refined as rotating group: C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C26(H26A,H26B,H26C) ; _shelx_res_file ; TITL tham1310_a.res in P2(1)/n tham1310.res created by SHELXL-2018/3 at 09:44:59 on 18-Oct-2023 CELL 1.54184 10.0374 12.7461 15.5693 90 93.567 90 ZERR 4 0.0001 0.0001 0.0002 0 0.001 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H O UNIT 104 96 12 L.S. 10 0 0 PLAN 20 SIZE 0.09 0.12 0.2 TEMP -113.15(10) CONF BOND list 4 MORE -1 BOND $H fmap 2 53 acta REM REM REM WGHT 0.035500 0.616300 EXTI 0.001214 FVAR 5.59811 C1 1 0.578471 0.306508 0.569123 11.00000 0.02201 0.02477 = 0.01941 0.00206 0.00048 0.00143 O1 3 0.500686 0.363918 0.620570 11.00000 0.02535 0.02563 = 0.02498 -0.00507 0.00205 -0.00152 O2 3 0.588416 0.085820 0.431991 11.00000 0.03325 0.02417 = 0.03558 -0.00410 0.01215 -0.00074 C2 1 0.716564 0.349613 0.569278 11.00000 0.02460 0.03145 = 0.02548 0.00050 -0.00096 -0.00551 AFIX 23 H2A 2 0.769126 0.323601 0.620843 11.00000 -1.20000 H2B 2 0.712572 0.427063 0.573165 11.00000 -1.20000 AFIX 0 O3 3 0.167092 0.434642 0.333877 11.00000 0.04506 0.02862 = 0.03661 0.00209 -0.01219 0.00675 C3 1 0.787718 0.319061 0.488790 11.00000 0.02277 0.03437 = 0.02552 0.00476 0.00147 -0.00435 C4 1 0.768890 0.200742 0.474287 11.00000 0.02183 0.03415 = 0.03084 0.00203 0.00522 0.00255 AFIX 23 H4A 2 0.805253 0.181884 0.418671 11.00000 -1.20000 H4B 2 0.821886 0.162770 0.520163 11.00000 -1.20000 AFIX 0 C5 1 0.625798 0.163329 0.473567 11.00000 0.02446 0.02256 = 0.02309 0.00457 0.00457 0.00252 C6 1 0.533828 0.220732 0.526140 11.00000 0.02058 0.02244 = 0.01961 0.00272 0.00155 0.00091 C7 1 0.391562 0.182306 0.528126 11.00000 0.02053 0.01943 = 0.02047 0.00002 0.00319 0.00010 AFIX 13 H7 2 0.393209 0.104510 0.536438 11.00000 -1.20000 AFIX 0 C8 1 0.327252 0.231809 0.603984 11.00000 0.02134 0.02357 = 0.01727 0.00203 0.00093 0.00430 C9 1 0.380655 0.319959 0.642722 11.00000 0.02232 0.02601 = 0.01880 0.00117 0.00014 0.00313 C10 1 0.320311 0.374306 0.709145 11.00000 0.03118 0.02827 = 0.02065 -0.00360 -0.00187 0.00577 AFIX 43 H10 2 0.361250 0.435177 0.734150 11.00000 -1.20000 AFIX 0 C11 1 0.202680 0.338333 0.736893 11.00000 0.03106 0.03565 = 0.01885 -0.00118 0.00270 0.01120 AFIX 43 H11 2 0.160880 0.375021 0.781017 11.00000 -1.20000 AFIX 0 C12 1 0.141831 0.246673 0.700652 11.00000 0.02540 0.03292 = 0.01930 0.00545 0.00277 0.00844 C13 1 0.205192 0.192025 0.634346 11.00000 0.02237 0.02668 = 0.01873 0.00496 0.00150 0.00436 C14 1 0.143408 0.099705 0.600106 11.00000 0.02531 0.02818 = 0.02583 0.00391 0.00505 0.00219 AFIX 43 H14 2 0.184502 0.061762 0.556377 11.00000 -1.20000 AFIX 0 C15 1 0.025183 0.064380 0.629194 11.00000 0.02734 0.03141 = 0.03496 0.00716 0.00464 -0.00109 AFIX 43 H15 2 -0.014485 0.002237 0.605617 11.00000 -1.20000 AFIX 0 C16 1 -0.037886 0.119663 0.693852 11.00000 0.02522 0.04102 = 0.03684 0.01168 0.01063 0.00294 AFIX 43 H16 2 -0.120297 0.095160 0.713106 11.00000 -1.20000 AFIX 0 C17 1 0.019296 0.208291 0.728792 11.00000 0.02863 0.04134 = 0.02627 0.00740 0.00917 0.01011 AFIX 43 H17 2 -0.023578 0.244776 0.772569 11.00000 -1.20000 AFIX 0 C18 1 0.729195 0.381189 0.411215 11.00000 0.04104 0.04199 = 0.02968 0.01108 -0.00164 -0.00834 AFIX 137 H18A 2 0.632864 0.368478 0.403924 11.00000 -1.50000 H18B 2 0.771729 0.358647 0.359326 11.00000 -1.50000 H18C 2 0.745521 0.456222 0.420725 11.00000 -1.50000 AFIX 0 C19 1 0.936569 0.343392 0.503177 11.00000 0.02579 0.05523 = 0.04032 0.00474 0.00365 -0.00997 AFIX 137 H19A 2 0.948564 0.418341 0.515388 11.00000 -1.50000 H19B 2 0.982160 0.325119 0.451362 11.00000 -1.50000 H19C 2 0.974406 0.302313 0.552006 11.00000 -1.50000 AFIX 0 C20 1 0.311291 0.206665 0.443658 11.00000 0.01909 0.02309 = 0.01926 -0.00117 0.00440 -0.00231 C21 1 0.276073 0.309197 0.422737 11.00000 0.02431 0.02319 = 0.02207 -0.00371 -0.00002 -0.00164 AFIX 43 H21 2 0.305175 0.364828 0.459936 11.00000 -1.20000 AFIX 0 C22 1 0.198287 0.331292 0.347539 11.00000 0.02313 0.02613 = 0.02402 0.00137 0.00248 -0.00036 C23 1 0.156966 0.251147 0.292111 11.00000 0.02718 0.03686 = 0.01978 0.00043 -0.00134 -0.00639 AFIX 43 H23 2 0.103427 0.265881 0.241066 11.00000 -1.20000 AFIX 0 C24 1 0.194897 0.149064 0.312218 11.00000 0.04104 0.03018 = 0.02380 -0.00599 -0.00046 -0.01096 AFIX 43 H24 2 0.168343 0.093829 0.273918 11.00000 -1.20000 AFIX 0 C25 1 0.270926 0.126199 0.387271 11.00000 0.03552 0.02273 = 0.02407 -0.00222 0.00316 -0.00414 AFIX 43 H25 2 0.295499 0.055721 0.400262 11.00000 -1.20000 AFIX 0 C26 1 0.067680 0.458909 0.267853 11.00000 0.03880 0.04526 = 0.04753 0.01600 -0.00981 0.00440 AFIX 137 H26A 2 0.099229 0.438437 0.211943 11.00000 -1.50000 H26B 2 0.049711 0.534480 0.267990 11.00000 -1.50000 H26C 2 -0.014438 0.420542 0.278105 11.00000 -1.50000 AFIX 0 HKLF 4 REM tham1310_a.res in P2(1)/n REM wR2 = 0.0859, GooF = S = 1.056, Restrained GooF = 1.056 for all data REM R1 = 0.0340 for 4058 Fo > 4sig(Fo) and 0.0357 for all 4301 data REM 266 parameters refined using 0 restraints END WGHT 0.0355 0.6163 REM Highest difference peak 0.262, deepest hole -0.164, 1-sigma level 0.034 Q1 1 0.4640 0.2011 0.5272 11.00000 0.05 0.26 Q2 1 0.3548 0.1976 0.4833 11.00000 0.05 0.25 Q3 1 0.7506 0.3362 0.5265 11.00000 0.05 0.23 Q4 1 0.5771 0.1977 0.5012 11.00000 0.05 0.23 Q5 1 0.3588 0.2040 0.5686 11.00000 0.05 0.23 Q6 1 0.6969 0.1855 0.4789 11.00000 0.05 0.22 Q7 1 0.5636 0.2413 0.5620 11.00000 0.05 0.21 Q8 1 0.7776 0.2618 0.4818 11.00000 0.05 0.21 Q9 1 0.3741 0.2583 0.6394 11.00000 0.05 0.20 Q10 1 0.2662 0.2155 0.6153 11.00000 0.05 0.20 Q11 1 0.3343 0.3552 0.6668 11.00000 0.05 0.20 Q12 1 0.1728 0.2206 0.6689 11.00000 0.05 0.20 Q13 1 0.6444 0.3329 0.5631 11.00000 0.05 0.20 Q14 1 0.3496 0.2828 0.6116 11.00000 0.05 0.20 Q15 1 0.5441 0.2808 0.5269 11.00000 0.05 0.19 Q16 1 0.1603 0.3041 0.7038 11.00000 0.05 0.18 Q17 1 0.1572 0.1614 0.6055 11.00000 0.05 0.18 Q18 1 0.8554 0.3350 0.4958 11.00000 0.05 0.18 Q19 1 0.0859 0.2203 0.7185 11.00000 0.05 0.18 Q20 1 0.2507 0.3209 0.3767 11.00000 0.05 0.18 ; _shelx_res_checksum 39291 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 C1 C 0.57847(9) 0.30651(7) 0.56912(6) 0.02210(19) Uani 1 1 d . . . . . O1 O 0.50069(7) 0.36392(5) 0.62057(4) 0.02530(16) Uani 1 1 d . . . . . O2 O 0.58842(7) 0.08582(6) 0.43199(5) 0.03058(17) Uani 1 1 d . . . . . C2 C 0.71656(10) 0.34961(8) 0.56928(6) 0.0273(2) Uani 1 1 d . . . . . H2A H 0.769126 0.323601 0.620843 0.033 Uiso 1 1 calc R U . . . H2B H 0.712572 0.427063 0.573165 0.033 Uiso 1 1 calc R U . . . O3 O 0.16709(9) 0.43464(6) 0.33388(5) 0.0374(2) Uani 1 1 d . . . . . C3 C 0.78772(10) 0.31906(8) 0.48879(6) 0.0276(2) Uani 1 1 d . . . . . C4 C 0.76889(10) 0.20074(8) 0.47429(7) 0.0288(2) Uani 1 1 d . . . . . H4A H 0.805253 0.181884 0.418671 0.035 Uiso 1 1 calc R U . . . H4B H 0.821886 0.162770 0.520163 0.035 Uiso 1 1 calc R U . . . C5 C 0.62580(10) 0.16333(7) 0.47357(6) 0.0232(2) Uani 1 1 d . . . . . C6 C 0.53383(9) 0.22073(7) 0.52614(6) 0.02086(19) Uani 1 1 d . . . . . C7 C 0.39156(9) 0.18231(7) 0.52813(6) 0.02006(19) Uani 1 1 d . . . . . H7 H 0.393209 0.104510 0.536438 0.024 Uiso 1 1 calc R U . . . C8 C 0.32725(9) 0.23181(7) 0.60398(6) 0.02074(19) Uani 1 1 d . . . . . C9 C 0.38065(9) 0.31996(8) 0.64272(6) 0.02242(19) Uani 1 1 d . . . . . C10 C 0.32031(10) 0.37431(8) 0.70914(6) 0.0268(2) Uani 1 1 d . . . . . H10 H 0.361250 0.435177 0.734150 0.032 Uiso 1 1 calc R U . . . C11 C 0.20268(10) 0.33833(8) 0.73689(6) 0.0285(2) Uani 1 1 d . . . . . H11 H 0.160880 0.375021 0.781017 0.034 Uiso 1 1 calc R U . . . C12 C 0.14183(10) 0.24667(8) 0.70065(6) 0.0258(2) Uani 1 1 d . . . . . C13 C 0.20519(9) 0.19203(8) 0.63435(6) 0.02258(19) Uani 1 1 d . . . . . C14 C 0.14341(10) 0.09970(8) 0.60011(6) 0.0263(2) Uani 1 1 d . . . . . H14 H 0.184502 0.061762 0.556377 0.032 Uiso 1 1 calc R U . . . C15 C 0.02518(11) 0.06438(9) 0.62919(7) 0.0311(2) Uani 1 1 d . . . . . H15 H -0.014485 0.002237 0.605617 0.037 Uiso 1 1 calc R U . . . C16 C -0.03789(11) 0.11966(9) 0.69385(7) 0.0340(2) Uani 1 1 d . . . . . H16 H -0.120297 0.095160 0.713106 0.041 Uiso 1 1 calc R U . . . C17 C 0.01930(11) 0.20829(9) 0.72879(7) 0.0318(2) Uani 1 1 d . . . . . H17 H -0.023578 0.244776 0.772569 0.038 Uiso 1 1 calc R U . . . C18 C 0.72919(12) 0.38119(10) 0.41122(7) 0.0377(3) Uani 1 1 d . . . . . H18A H 0.632864 0.368478 0.403924 0.057 Uiso 1 1 calc R U . . . H18B H 0.771729 0.358647 0.359326 0.057 Uiso 1 1 calc R U . . . H18C H 0.745521 0.456222 0.420725 0.057 Uiso 1 1 calc R U . . . C19 C 0.93657(11) 0.34339(11) 0.50318(8) 0.0404(3) Uani 1 1 d . . . . . H19A H 0.948564 0.418341 0.515388 0.061 Uiso 1 1 calc R U . . . H19B H 0.982160 0.325119 0.451362 0.061 Uiso 1 1 calc R U . . . H19C H 0.974406 0.302313 0.552006 0.061 Uiso 1 1 calc R U . . . C20 C 0.31129(9) 0.20666(7) 0.44366(6) 0.02035(19) Uani 1 1 d . . . . . C21 C 0.27607(9) 0.30920(7) 0.42274(6) 0.0233(2) Uani 1 1 d . . . . . H21 H 0.305175 0.364828 0.459936 0.028 Uiso 1 1 calc R U . . . C22 C 0.19829(10) 0.33129(8) 0.34754(6) 0.0244(2) Uani 1 1 d . . . . . C23 C 0.15697(10) 0.25115(8) 0.29211(6) 0.0281(2) Uani 1 1 d . . . . . H23 H 0.103427 0.265881 0.241066 0.034 Uiso 1 1 calc R U . . . C24 C 0.19490(12) 0.14906(9) 0.31222(7) 0.0318(2) Uani 1 1 d . . . . . H24 H 0.168343 0.093829 0.273918 0.038 Uiso 1 1 calc R U . . . C25 C 0.27093(11) 0.12620(8) 0.38727(6) 0.0274(2) Uani 1 1 d . . . . . H25 H 0.295499 0.055721 0.400262 0.033 Uiso 1 1 calc R U . . . C26 C 0.06768(13) 0.45891(11) 0.26785(9) 0.0444(3) Uani 1 1 d . . . . . H26A H 0.099229 0.438437 0.211943 0.067 Uiso 1 1 calc R U . . . H26B H 0.049711 0.534480 0.267990 0.067 Uiso 1 1 calc R U . . . H26C H -0.014438 0.420542 0.278105 0.067 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 C1 0.0220(4) 0.0248(4) 0.0194(4) 0.0021(3) 0.0005(3) 0.0014(3) O1 0.0253(3) 0.0256(3) 0.0250(3) -0.0051(3) 0.0020(3) -0.0015(3) O2 0.0332(4) 0.0242(4) 0.0356(4) -0.0041(3) 0.0121(3) -0.0007(3) C2 0.0246(5) 0.0315(5) 0.0255(5) 0.0005(4) -0.0010(4) -0.0055(4) O3 0.0451(5) 0.0286(4) 0.0366(4) 0.0021(3) -0.0122(3) 0.0068(3) C3 0.0228(5) 0.0344(5) 0.0255(5) 0.0048(4) 0.0015(4) -0.0043(4) C4 0.0218(5) 0.0342(5) 0.0308(5) 0.0020(4) 0.0052(4) 0.0026(4) C5 0.0245(5) 0.0226(4) 0.0231(4) 0.0046(4) 0.0046(4) 0.0025(4) C6 0.0206(4) 0.0224(4) 0.0196(4) 0.0027(3) 0.0015(3) 0.0009(3) C7 0.0205(4) 0.0194(4) 0.0205(4) 0.0000(3) 0.0032(3) 0.0001(3) C8 0.0213(4) 0.0236(4) 0.0173(4) 0.0020(3) 0.0009(3) 0.0043(3) C9 0.0223(4) 0.0260(5) 0.0188(4) 0.0012(3) 0.0001(3) 0.0031(3) C10 0.0312(5) 0.0283(5) 0.0206(4) -0.0036(4) -0.0019(4) 0.0058(4) C11 0.0311(5) 0.0356(5) 0.0188(4) -0.0012(4) 0.0027(4) 0.0112(4) C12 0.0254(5) 0.0329(5) 0.0193(4) 0.0055(4) 0.0028(3) 0.0084(4) C13 0.0224(4) 0.0267(5) 0.0187(4) 0.0050(3) 0.0015(3) 0.0044(4) C14 0.0253(5) 0.0282(5) 0.0258(5) 0.0039(4) 0.0050(4) 0.0022(4) C15 0.0273(5) 0.0314(5) 0.0350(6) 0.0072(4) 0.0046(4) -0.0011(4) C16 0.0252(5) 0.0410(6) 0.0368(6) 0.0117(5) 0.0106(4) 0.0029(4) C17 0.0286(5) 0.0413(6) 0.0263(5) 0.0074(4) 0.0092(4) 0.0101(4) C18 0.0410(6) 0.0420(6) 0.0297(5) 0.0111(5) -0.0016(5) -0.0083(5) C19 0.0258(5) 0.0552(7) 0.0403(6) 0.0047(5) 0.0036(4) -0.0100(5) C20 0.0191(4) 0.0231(4) 0.0193(4) -0.0012(3) 0.0044(3) -0.0023(3) C21 0.0243(5) 0.0232(5) 0.0221(4) -0.0037(4) 0.0000(3) -0.0016(4) C22 0.0231(4) 0.0261(5) 0.0240(5) 0.0014(4) 0.0025(4) -0.0004(4) C23 0.0272(5) 0.0369(6) 0.0198(4) 0.0004(4) -0.0013(4) -0.0064(4) C24 0.0410(6) 0.0302(5) 0.0238(5) -0.0060(4) -0.0005(4) -0.0110(4) C25 0.0355(5) 0.0227(5) 0.0241(5) -0.0022(4) 0.0032(4) -0.0041(4) C26 0.0388(6) 0.0453(7) 0.0475(7) 0.0160(6) -0.0098(5) 0.0044(5) 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_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -4 1 5 0.0602 4 -1 -5 0.0602 -3 1 -5 0.0781 5 -3 5 0.0789 -3 0 5 0.0485 5 -5 -3 0.0569 0 5 -1 0.0431 0 -8 1 0.0454 0 -8 -2 0.0491 0 8 0 0.0397 1 4 -9 0.0754 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 O1 C1 C2 111.53(8) . . ? C6 C1 O1 122.88(9) . . ? C6 C1 C2 125.57(9) . . ? C1 O1 C9 117.72(7) . . ? C1 C2 H2A 109.1 . . ? C1 C2 H2B 109.1 . . ? C1 C2 C3 112.70(8) . . ? H2A C2 H2B 107.8 . . ? C3 C2 H2A 109.1 . . ? C3 C2 H2B 109.1 . . ? C22 O3 C26 117.76(9) . . ? C2 C3 C4 108.12(8) . . ? C18 C3 C2 109.80(9) . . ? C18 C3 C4 110.77(9) . . ? C19 C3 C2 109.26(9) . . ? C19 C3 C4 109.34(9) . . ? C19 C3 C18 109.53(9) . . ? C3 C4 H4A 108.6 . . ? C3 C4 H4B 108.6 . . ? H4A C4 H4B 107.6 . . ? C5 C4 C3 114.77(8) . . ? C5 C4 H4A 108.6 . . ? C5 C4 H4B 108.6 . . ? O2 C5 C4 121.11(9) . . ? O2 C5 C6 120.90(9) . . ? C6 C5 C4 117.96(9) . . ? C1 C6 C5 118.79(9) . . ? C1 C6 C7 122.64(8) . . ? C5 C6 C7 118.55(8) . . ? C6 C7 H7 108.4 . . ? C6 C7 C8 109.22(7) . . ? C6 C7 C20 111.35(7) . . ? C8 C7 H7 108.4 . . ? C8 C7 C20 110.95(7) . . ? C20 C7 H7 108.4 . . ? C9 C8 C7 120.68(8) . . ? C9 C8 C13 117.68(8) . . ? C13 C8 C7 121.55(8) . . ? O1 C9 C10 113.67(8) . . ? C8 C9 O1 122.87(8) . . ? C8 C9 C10 123.46(9) . . ? C9 C10 H10 120.4 . . ? C11 C10 C9 119.15(9) . . ? C11 C10 H10 120.4 . . ? C10 C11 H11 119.6 . . ? C10 C11 C12 120.75(9) . . ? C12 C11 H11 119.6 . . ? C11 C12 C13 119.29(9) . . ? C17 C12 C11 121.42(9) . . ? C17 C12 C13 119.29(10) . . ? C12 C13 C8 119.63(9) . . ? C14 C13 C8 122.16(8) . . ? C14 C13 C12 118.20(9) . . ? C13 C14 H14 119.5 . . ? C15 C14 C13 121.00(9) . . ? C15 C14 H14 119.5 . . ? C14 C15 H15 119.8 . . ? C14 C15 C16 120.49(10) . . ? C16 C15 H15 119.8 . . ? C15 C16 H16 119.9 . . ? C17 C16 C15 120.11(10) . . ? C17 C16 H16 119.9 . . ? C12 C17 H17 119.5 . . ? C16 C17 C12 120.91(10) . . ? C16 C17 H17 119.5 . . ? C3 C18 H18A 109.5 . . ? C3 C18 H18B 109.5 . . ? C3 C18 H18C 109.5 . . ? H18A C18 H18B 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C3 C19 H19A 109.5 . . ? C3 C19 H19B 109.5 . . ? C3 C19 H19C 109.5 . . ? H19A C19 H19B 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 C20 C7 120.37(8) . . ? C21 C20 C25 119.04(9) . . ? C25 C20 C7 120.58(8) . . ? C20 C21 H21 119.7 . . ? C20 C21 C22 120.56(9) . . ? C22 C21 H21 119.7 . . ? O3 C22 C21 115.83(9) . . ? O3 C22 C23 123.86(9) . . ? C23 C22 C21 120.31(9) . . ? C22 C23 H23 120.5 . . ? C22 C23 C24 118.98(9) . . ? C24 C23 H23 120.5 . . ? C23 C24 H24 119.4 . . ? C23 C24 C25 121.12(9) . . ? C25 C24 H24 119.4 . . ? C20 C25 H25 120.0 . . ? C24 C25 C20 119.96(9) . . ? C24 C25 H25 120.0 . . ? O3 C26 H26A 109.5 . . ? O3 C26 H26B 109.5 . . ? O3 C26 H26C 109.5 . . ? H26A C26 H26B 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? 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 C1 O1 1.3655(11) . ? C1 C2 1.4909(13) . ? C1 C6 1.3441(13) . ? O1 C9 1.3914(12) . ? O2 C5 1.2270(12) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C2 C3 1.5308(14) . ? O3 C22 1.3676(12) . ? O3 C26 1.4214(13) . ? C3 C4 1.5349(15) . ? C3 C18 1.5306(14) . ? C3 C19 1.5287(14) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C4 C5 1.5127(13) . ? C5 C6 1.4668(13) . ? C6 C7 1.5118(12) . ? C7 H7 1.0000 . ? C7 C8 1.5181(12) . ? C7 C20 1.5308(12) . ? C8 C9 1.3687(13) . ? C8 C13 1.4331(13) . ? C9 C10 1.4121(13) . ? C10 H10 0.9500 . ? C10 C11 1.3618(15) . ? C11 H11 0.9500 . ? C11 C12 1.4190(15) . ? C12 C13 1.4272(13) . ? C12 C17 1.4181(14) . ? C13 C14 1.4186(14) . ? C14 H14 0.9500 . ? C14 C15 1.3722(14) . ? C15 H15 0.9500 . ? C15 C16 1.4107(16) . ? C16 H16 0.9500 . ? C16 C17 1.3648(17) . ? C17 H17 0.9500 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C21 1.3873(13) . ? C20 C25 1.3937(13) . ? C21 H21 0.9500 . ? C21 C22 1.3950(13) . ? C22 C23 1.3841(14) . ? C23 H23 0.9500 . ? C23 C24 1.3861(16) . ? C24 H24 0.9500 . ? C24 C25 1.3863(15) . ? C25 H25 0.9500 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? 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 C1 O1 C9 C8 -11.60(13) . . . . ? C1 O1 C9 C10 167.88(8) . . . . ? C1 C2 C3 C4 -47.86(11) . . . . ? C1 C2 C3 C18 73.09(11) . . . . ? C1 C2 C3 C19 -166.77(9) . . . . ? C1 C6 C7 C8 -17.51(12) . . . . ? C1 C6 C7 C20 105.36(10) . . . . ? O1 C1 C2 C3 -156.64(8) . . . . ? O1 C1 C6 C5 -179.01(8) . . . . ? O1 C1 C6 C7 2.42(14) . . . . ? O1 C9 C10 C11 -179.56(8) . . . . ? O2 C5 C6 C1 -178.59(9) . . . . ? O2 C5 C6 C7 0.04(13) . . . . ? C2 C1 O1 C9 -165.31(8) . . . . ? C2 C1 C6 C5 -0.66(14) . . . . ? C2 C1 C6 C7 -179.22(9) . . . . ? C2 C3 C4 C5 51.68(11) . . . . ? O3 C22 C23 C24 179.77(10) . . . . ? C3 C4 C5 O2 151.48(9) . . . . ? C3 C4 C5 C6 -30.27(12) . . . . ? C4 C5 C6 C1 3.16(13) . . . . ? C4 C5 C6 C7 -178.21(8) . . . . ? C5 C6 C7 C8 163.92(8) . . . . ? C5 C6 C7 C20 -73.21(10) . . . . ? C6 C1 O1 C9 13.26(13) . . . . ? C6 C1 C2 C3 24.84(14) . . . . ? C6 C7 C8 C9 18.66(11) . . . . ? C6 C7 C8 C13 -164.97(8) . . . . ? C6 C7 C20 C21 -70.60(11) . . . . ? C6 C7 C20 C25 110.30(10) . . . . ? C7 C8 C9 O1 -5.50(14) . . . . ? C7 C8 C9 C10 175.06(8) . . . . ? C7 C8 C13 C12 -174.27(8) . . . . ? C7 C8 C13 C14 5.16(14) . . . . ? C7 C20 C21 C22 -177.36(8) . . . . ? C7 C20 C25 C24 178.08(9) . . . . ? C8 C7 C20 C21 51.27(11) . . . . ? C8 C7 C20 C25 -127.82(9) . . . . ? C8 C9 C10 C11 -0.08(15) . . . . ? C8 C13 C14 C15 -178.75(9) . . . . ? C9 C8 C13 C12 2.20(13) . . . . ? C9 C8 C13 C14 -178.36(9) . . . . ? C9 C10 C11 C12 0.84(15) . . . . ? C10 C11 C12 C13 -0.04(14) . . . . ? C10 C11 C12 C17 -179.93(9) . . . . ? C11 C12 C13 C8 -1.51(13) . . . . ? C11 C12 C13 C14 179.04(9) . . . . ? C11 C12 C17 C16 -179.58(10) . . . . ? C12 C13 C14 C15 0.69(14) . . . . ? C13 C8 C9 O1 177.99(8) . . . . ? C13 C8 C9 C10 -1.45(14) . . . . ? C13 C12 C17 C16 0.53(15) . . . . ? C13 C14 C15 C16 0.24(16) . . . . ? C14 C15 C16 C17 -0.80(16) . . . . ? C15 C16 C17 C12 0.41(16) . . . . ? C17 C12 C13 C8 178.39(9) . . . . ? C17 C12 C13 C14 -1.07(13) . . . . ? C18 C3 C4 C5 -68.66(11) . . . . ? C19 C3 C4 C5 170.54(9) . . . . ? C20 C7 C8 C9 -104.45(10) . . . . ? C20 C7 C8 C13 71.92(10) . . . . ? C20 C21 C22 O3 178.76(9) . . . . ? C20 C21 C22 C23 -1.01(15) . . . . ? C21 C20 C25 C24 -1.02(15) . . . . ? C21 C22 C23 C24 -0.47(15) . . . . ? C22 C23 C24 C25 1.21(16) . . . . ? C23 C24 C25 C20 -0.46(16) . . . . ? C25 C20 C21 C22 1.75(14) . . . . ? C26 O3 C22 C21 -167.98(10) . . . . ? C26 O3 C22 C23 11.78(15) . . . . ?