#------------------------------------------------------------------------------ #$Date: 2024-05-05 07:01:22 +0300 (Sun, 05 May 2024) $ #$Revision: 291688 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/98/7159879.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_7159879 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 'C17 H10 O2' _chemical_formula_sum 'C17 H10 O2' _chemical_formula_weight 246.25 _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 2023-10-17 _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 95.5510(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.12120(10) _cell_length_b 12.50200(10) _cell_length_c 12.82470(10) _cell_measurement_reflns_used 8157 _cell_measurement_temperature 160.0(1) _cell_measurement_theta_max 79.3150 _cell_measurement_theta_min 6.8450 _cell_volume 1136.42(2) _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 0.998 _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 -26.00 0.00 0.50 0.56 -- -10.00 -47.00-120.24 52 2 \w 0.00 26.00 0.50 0.56 -- 10.00 47.00 81.83 52 3 \w 1.00 27.00 0.50 0.56 -- 10.00 46.00-139.18 52 4 \w -31.00 -5.00 0.50 0.56 -- -14.00 -43.00 139.18 52 5 \w -45.00 -17.00 0.50 0.56 -- -26.00 -36.00 47.81 56 6 \w 0.00 71.00 0.50 0.56 -- 50.09 -77.00-120.00 142 7 \w -134.00 -54.00 0.50 0.56 -- -62.00 -30.00 63.65 160 8 \w -71.00 -18.00 0.50 2.22 -- -90.00 61.00-150.00 106 9 \w -161.00-122.00 0.50 2.22 -- -90.00 -45.00 60.00 78 10 \w -161.00-122.00 0.50 2.22 -- -90.00 -45.00 90.00 78 11 \w 42.00 106.00 0.50 2.22 -- 111.50 -97.00-163.27 128 12 \w 41.00 105.00 0.50 2.22 -- 111.50 -77.00 -60.00 128 13 \w 104.00 178.00 0.50 2.22 -- 111.50 15.00 0.00 148 14 \w 127.00 178.00 0.50 2.22 -- 111.50 61.00 0.00 102 15 \w 41.00 105.00 0.50 2.22 -- 111.50 -77.00 90.00 128 16 \w 41.00 71.00 0.50 2.22 -- 111.50 -61.00-120.00 60 17 \w 127.00 178.00 0.50 2.22 -- 111.50 61.00 120.00 102 18 \w 41.00 105.00 0.50 2.22 -- 111.50 -77.00 120.00 128 19 \w 43.00 111.00 0.50 2.22 -- 111.50-125.00-150.00 136 20 \w 41.00 71.00 0.50 2.22 -- 111.50 -61.00 0.00 60 21 \w 66.00 105.00 0.50 2.22 -- 111.50 -95.00 -90.00 78 22 \w 132.00 178.00 0.50 2.22 -- 111.50 77.00-150.00 92 23 \w 41.00 66.00 0.50 2.22 -- 111.50 -61.00-180.00 50 24 \w 41.00 67.00 0.50 2.22 -- 111.50 -61.00 -90.00 52 25 \w 126.00 152.00 0.50 2.22 -- 111.50 45.00 -60.00 52 26 \w 126.00 163.00 0.50 2.22 -- 111.50 101.00-123.00 74 27 \w 42.00 68.00 0.50 2.22 -- 111.50 -77.00 -90.00 52 28 \w 44.00 70.00 0.50 2.22 -- 111.50 -77.00-120.00 52 29 \w 68.00 104.00 0.50 2.22 -- 111.50 -77.00 150.00 72 30 \w 57.00 91.00 0.50 2.22 -- 111.50 -95.00 120.00 68 31 \w 122.00 147.00 0.50 2.22 -- 111.50 45.00 150.00 50 32 \w 144.00 178.00 0.50 2.22 -- 111.50 77.00 -60.00 68 33 \w 81.00 135.00 0.50 2.22 -- 111.50 -83.00-107.83 108 34 \w 133.00 176.00 0.50 2.22 -- 111.50 125.00 150.00 86 35 \w 131.00 164.00 0.50 2.22 -- 111.50 61.00-120.00 66 36 \w 106.00 132.00 0.50 2.22 -- 111.50 -79.00 -6.06 52 37 \w 70.00 101.00 0.50 2.22 -- 111.50 -95.00 90.00 62 38 \w 73.00 98.00 0.50 2.22 -- 111.50 -95.00 150.00 50 39 \w 72.00 98.00 0.50 2.22 -- 111.50-125.00 90.00 52 40 \w 113.00 139.00 0.50 2.22 -- 111.50 15.00 60.00 52 41 \w 62.00 88.00 0.50 2.22 -- 111.50 -79.00 -6.06 52 ; _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 -0.0116762000 _diffrn_orient_matrix_UB_12 0.1169436000 _diffrn_orient_matrix_UB_13 0.0366944000 _diffrn_orient_matrix_UB_21 0.2167075000 _diffrn_orient_matrix_UB_22 0.0083068000 _diffrn_orient_matrix_UB_23 0.0074865000 _diffrn_orient_matrix_UB_31 -0.0117082000 _diffrn_orient_matrix_UB_32 0.0378300000 _diffrn_orient_matrix_UB_33 -0.1147791000 _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 0.0160 _diffrn_reflns_av_unetI/netI 0.0144 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 13198 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 79.513 _diffrn_reflns_theta_min 4.952 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.754 _exptl_absorpt_correction_T_max 0.976 _exptl_absorpt_correction_T_min 0.932 _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 1.439 _exptl_crystal_description plate _exptl_crystal_F_000 512 _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.03 _refine_diff_density_max 0.245 _refine_diff_density_min -0.150 _refine_diff_density_rms 0.034 _refine_ls_extinction_coef 0.0021(3) _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 1.097 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 173 _refine_ls_number_reflns 2461 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.097 _refine_ls_R_factor_all 0.0363 _refine_ls_R_factor_gt 0.0339 _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^)+(0.0554P)^2^+0.1638P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1013 _refine_ls_wR_factor_ref 0.1034 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2249 _reflns_number_total 2461 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ob00093e2.cif _cod_data_source_block tham1110 _cod_depositor_comments 'Adding full bibliography for 7159879--7159880.cif.' _cod_database_code 7159879 _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 0.978 _shelx_estimated_absorpt_t_min 0.908 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups 2.a Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C14(H14), C15(H15), C16(H16), C17(H17) ; _shelx_res_file ; TITL tham1110_a.res in P2(1)/n tham1110.res created by SHELXL-2018/3 at 09:35:17 on 17-Oct-2023 CELL 1.54184 7.1212 12.502 12.8247 90 95.551 90 ZERR 4 0.0001 0.0001 0.0001 0 0.001 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H O UNIT 68 40 8 EQIV $1 0.5+X,1.5-Y,0.5+Z L.S. 10 PLAN 20 SIZE 0.03 0.09 0.13 TEMP -113.15(10) CONF HTAB C14 O2 HTAB C17 O2_$1 list 4 MORE -1 BOND $H fmap 2 53 acta REM REM REM WGHT 0.055400 0.163800 EXTI 0.002078 FVAR 4.25804 O1 3 0.308976 0.399831 0.603409 11.00000 0.03495 0.02981 = 0.02912 0.00373 0.00314 0.00191 C1 1 0.244380 0.347679 0.512967 11.00000 0.02456 0.03022 = 0.03219 0.00070 0.00682 0.00162 O2 3 0.164707 0.567258 0.333315 11.00000 0.07022 0.03257 = 0.03028 0.00279 -0.01517 -0.00296 C2 1 0.235383 0.236413 0.518196 11.00000 0.03412 0.03013 = 0.04378 0.00602 0.01140 0.00334 AFIX 43 H2 2 0.274474 0.199860 0.581538 11.00000 -1.20000 AFIX 0 C3 1 0.168707 0.180577 0.429711 11.00000 0.03654 0.02712 = 0.05576 -0.00242 0.01370 -0.00103 AFIX 43 H3 2 0.161250 0.104769 0.432299 11.00000 -1.20000 AFIX 0 C4 1 0.111804 0.233899 0.336076 11.00000 0.03304 0.03430 = 0.04596 -0.00962 0.00819 -0.00411 AFIX 43 H4 2 0.065412 0.194530 0.275645 11.00000 -1.20000 AFIX 0 C5 1 0.123345 0.343592 0.331925 11.00000 0.02892 0.03376 = 0.03501 -0.00360 0.00391 -0.00137 AFIX 43 H5 2 0.085476 0.379727 0.268179 11.00000 -1.20000 AFIX 0 C6 1 0.190529 0.402815 0.420927 11.00000 0.02314 0.02850 = 0.03206 -0.00083 0.00486 0.00042 C7 1 0.206644 0.519880 0.416224 11.00000 0.02825 0.02906 = 0.02788 0.00092 -0.00050 0.00087 C8 1 0.274713 0.572576 0.515410 11.00000 0.02197 0.02924 = 0.02587 0.00005 0.00229 0.00150 C9 1 0.319103 0.509126 0.603339 11.00000 0.02413 0.03015 = 0.02840 0.00183 0.00460 0.00176 C10 1 0.380937 0.552035 0.702671 11.00000 0.03101 0.04249 = 0.02384 0.00277 0.00213 0.00181 AFIX 43 H10 2 0.409727 0.506149 0.761079 11.00000 -1.20000 AFIX 0 C11 1 0.398670 0.659557 0.713583 11.00000 0.02869 0.04473 = 0.02529 -0.00564 0.00194 -0.00085 AFIX 43 H11 2 0.440462 0.688479 0.780317 11.00000 -1.20000 AFIX 0 C12 1 0.356159 0.730083 0.627436 11.00000 0.02270 0.03508 = 0.02990 -0.00498 0.00395 -0.00103 C13 1 0.295288 0.687279 0.526819 11.00000 0.02118 0.02970 = 0.02776 -0.00230 0.00284 0.00100 C14 1 0.259649 0.760317 0.442911 11.00000 0.03019 0.02874 = 0.03174 -0.00093 0.00152 0.00241 AFIX 43 H14 2 0.221164 0.734185 0.374618 11.00000 -1.20000 AFIX 0 C15 1 0.280032 0.868699 0.458990 11.00000 0.03719 0.02986 = 0.04021 0.00169 0.00447 0.00253 AFIX 43 H15 2 0.255439 0.916272 0.401528 11.00000 -1.20000 AFIX 0 C16 1 0.336461 0.910128 0.558704 11.00000 0.03617 0.02828 = 0.04913 -0.00712 0.00709 -0.00218 AFIX 43 H16 2 0.347906 0.985206 0.568837 11.00000 -1.20000 AFIX 0 C17 1 0.374995 0.841700 0.641428 11.00000 0.03008 0.03804 = 0.03717 -0.01153 0.00412 -0.00343 AFIX 43 H17 2 0.414772 0.869623 0.708856 11.00000 -1.20000 AFIX 0 HKLF 4 REM tham1110_a.res in P2(1)/n REM wR2 = 0.1034, GooF = S = 1.097, Restrained GooF = 1.097 for all data REM R1 = 0.0339 for 2249 Fo > 4sig(Fo) and 0.0363 for all 2461 data REM 173 parameters refined using 0 restraints END WGHT 0.0554 0.1638 REM Highest difference peak 0.245, deepest hole -0.150, 1-sigma level 0.034 Q1 1 0.1950 0.4576 0.4223 11.00000 0.05 0.25 Q2 1 0.2837 0.6258 0.5209 11.00000 0.05 0.23 Q3 1 0.3240 0.7059 0.5736 11.00000 0.05 0.22 Q4 1 0.2344 0.5529 0.4745 11.00000 0.05 0.21 Q5 1 0.1988 0.3793 0.4664 11.00000 0.05 0.21 Q6 1 0.2879 0.5411 0.5592 11.00000 0.05 0.21 Q7 1 0.3631 0.5362 0.6547 11.00000 0.05 0.18 Q8 1 0.3806 0.7864 0.6281 11.00000 0.05 0.17 Q9 1 0.3800 0.6998 0.6621 11.00000 0.05 0.17 Q10 1 0.2686 0.7226 0.4885 11.00000 0.05 0.17 Q11 1 0.1790 0.3745 0.3788 11.00000 0.05 0.16 Q12 1 0.2673 0.8161 0.4550 11.00000 0.05 0.16 Q13 1 0.2270 0.2874 0.5185 11.00000 0.05 0.15 Q14 1 0.1498 0.2160 0.3834 11.00000 0.05 0.14 Q15 1 0.3655 0.6119 0.7015 11.00000 0.05 0.13 Q16 1 0.2921 0.8803 0.5104 11.00000 0.05 0.12 Q17 1 0.1706 0.6387 0.3446 11.00000 0.05 0.11 Q18 1 0.1689 0.2161 0.4766 11.00000 0.05 0.11 Q19 1 0.3126 0.4594 0.6037 11.00000 0.05 0.11 Q20 1 0.2456 0.2140 0.4663 11.00000 0.05 0.11 ; _shelx_res_checksum 13100 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 0.30898(10) 0.39983(5) 0.60341(5) 0.03129(19) Uani 1 1 d . . . . . C1 C 0.24438(13) 0.34768(8) 0.51297(7) 0.0287(2) Uani 1 1 d . . . . . O2 O 0.16471(13) 0.56726(6) 0.33332(6) 0.0457(2) Uani 1 1 d . . . . . C2 C 0.23538(15) 0.23641(8) 0.51820(8) 0.0355(2) Uani 1 1 d . . . . . H2 H 0.274474 0.199860 0.581538 0.043 Uiso 1 1 calc R U . . . C3 C 0.16871(15) 0.18058(8) 0.42971(9) 0.0392(3) Uani 1 1 d . . . . . H3 H 0.161250 0.104769 0.432299 0.047 Uiso 1 1 calc R U . . . C4 C 0.11180(15) 0.23390(8) 0.33608(9) 0.0375(2) Uani 1 1 d . . . . . H4 H 0.065412 0.194530 0.275645 0.045 Uiso 1 1 calc R U . . . C5 C 0.12335(13) 0.34359(8) 0.33193(8) 0.0325(2) Uani 1 1 d . . . . . H5 H 0.085476 0.379727 0.268179 0.039 Uiso 1 1 calc R U . . . C6 C 0.19053(12) 0.40282(7) 0.42093(7) 0.0278(2) Uani 1 1 d . . . . . C7 C 0.20664(13) 0.51988(8) 0.41622(7) 0.0286(2) Uani 1 1 d . . . . . C8 C 0.27471(12) 0.57258(7) 0.51541(7) 0.0257(2) Uani 1 1 d . . . . . C9 C 0.31910(12) 0.50913(8) 0.60334(7) 0.0274(2) Uani 1 1 d . . . . . C10 C 0.38094(14) 0.55203(8) 0.70267(7) 0.0325(2) Uani 1 1 d . . . . . H10 H 0.409727 0.506149 0.761079 0.039 Uiso 1 1 calc R U . . . C11 C 0.39867(13) 0.65956(8) 0.71358(7) 0.0329(2) Uani 1 1 d . . . . . H11 H 0.440462 0.688479 0.780317 0.040 Uiso 1 1 calc R U . . . C12 C 0.35616(12) 0.73008(8) 0.62744(7) 0.0291(2) Uani 1 1 d . . . . . C13 C 0.29529(12) 0.68728(7) 0.52682(7) 0.0262(2) Uani 1 1 d . . . . . C14 C 0.25965(13) 0.76032(8) 0.44291(7) 0.0303(2) Uani 1 1 d . . . . . H14 H 0.221164 0.734185 0.374618 0.036 Uiso 1 1 calc R U . . . C15 C 0.28003(15) 0.86870(8) 0.45899(8) 0.0357(2) Uani 1 1 d . . . . . H15 H 0.255439 0.916272 0.401528 0.043 Uiso 1 1 calc R U . . . C16 C 0.33646(15) 0.91013(8) 0.55870(9) 0.0377(2) Uani 1 1 d . . . . . H16 H 0.347906 0.985206 0.568837 0.045 Uiso 1 1 calc R U . . . C17 C 0.37499(14) 0.84170(8) 0.64143(8) 0.0350(2) Uani 1 1 d . . . . . H17 H 0.414772 0.869623 0.708856 0.042 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 0.0350(4) 0.0298(4) 0.0291(3) 0.0037(2) 0.0031(3) 0.0019(3) C1 0.0246(4) 0.0302(5) 0.0322(5) 0.0007(3) 0.0068(3) 0.0016(3) O2 0.0702(6) 0.0326(4) 0.0303(4) 0.0028(3) -0.0152(3) -0.0030(3) C2 0.0341(5) 0.0301(5) 0.0438(6) 0.0060(4) 0.0114(4) 0.0033(4) C3 0.0365(5) 0.0271(5) 0.0558(6) -0.0024(4) 0.0137(5) -0.0010(4) C4 0.0330(5) 0.0343(5) 0.0460(6) -0.0096(4) 0.0082(4) -0.0041(4) C5 0.0289(5) 0.0338(5) 0.0350(5) -0.0036(4) 0.0039(4) -0.0014(4) C6 0.0231(4) 0.0285(5) 0.0321(5) -0.0008(3) 0.0049(3) 0.0004(3) C7 0.0282(4) 0.0291(5) 0.0279(4) 0.0009(3) -0.0005(3) 0.0009(3) C8 0.0220(4) 0.0292(5) 0.0259(4) 0.0000(3) 0.0023(3) 0.0015(3) C9 0.0241(4) 0.0301(5) 0.0284(4) 0.0018(3) 0.0046(3) 0.0018(3) C10 0.0310(5) 0.0425(5) 0.0238(4) 0.0028(4) 0.0021(3) 0.0018(4) C11 0.0287(5) 0.0447(6) 0.0253(4) -0.0056(4) 0.0019(3) -0.0009(4) C12 0.0227(4) 0.0351(5) 0.0299(5) -0.0050(4) 0.0040(3) -0.0010(3) C13 0.0212(4) 0.0297(5) 0.0278(4) -0.0023(3) 0.0028(3) 0.0010(3) C14 0.0302(5) 0.0287(5) 0.0317(5) -0.0009(3) 0.0015(3) 0.0024(3) C15 0.0372(5) 0.0299(5) 0.0402(5) 0.0017(4) 0.0045(4) 0.0025(4) C16 0.0362(5) 0.0283(5) 0.0491(6) -0.0071(4) 0.0071(4) -0.0022(4) C17 0.0301(5) 0.0380(5) 0.0372(5) -0.0115(4) 0.0041(4) -0.0034(4) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 1 -1 0.0166 0 -1 1 0.0166 0 -1 -1 0.0432 0 1 1 0.0432 2 -1 -5 0.0460 1 -1 0 0.0474 -1 1 0 0.0474 -4 -5 0 0.0579 4 5 0 0.0579 -2 3 5 0.0325 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 C9 O1 C1 119.20(7) . . ? O1 C1 C2 116.55(8) . . ? O1 C1 C6 121.72(9) . . ? C6 C1 C2 121.73(9) . . ? C1 C2 H2 120.7 . . ? C3 C2 C1 118.68(9) . . ? C3 C2 H2 120.7 . . ? C2 C3 H3 119.5 . . ? C2 C3 C4 120.93(9) . . ? C4 C3 H3 119.5 . . ? C3 C4 H4 120.2 . . ? C5 C4 C3 119.67(10) . . ? C5 C4 H4 120.2 . . ? C4 C5 H5 119.6 . . ? C4 C5 C6 120.73(9) . . ? C6 C5 H5 119.6 . . ? C1 C6 C5 118.25(9) . . ? C1 C6 C7 120.86(8) . . ? C5 C6 C7 120.88(8) . . ? O2 C7 C6 120.15(8) . . ? O2 C7 C8 124.35(9) . . ? C6 C7 C8 115.51(8) . . ? C9 C8 C7 118.40(9) . . ? C9 C8 C13 118.07(8) . . ? C13 C8 C7 123.52(8) . . ? O1 C9 C8 124.24(8) . . ? O1 C9 C10 112.98(8) . . ? C8 C9 C10 122.78(9) . . ? C9 C10 H10 120.4 . . ? C11 C10 C9 119.16(9) . . ? C11 C10 H10 120.4 . . ? C10 C11 H11 119.2 . . ? C10 C11 C12 121.56(8) . . ? C12 C11 H11 119.2 . . ? C11 C12 C13 119.57(9) . . ? C17 C12 C11 120.22(9) . . ? C17 C12 C13 120.21(9) . . ? C12 C13 C8 118.85(8) . . ? C14 C13 C8 123.60(8) . . ? C14 C13 C12 117.55(8) . . ? C13 C14 H14 119.6 . . ? C15 C14 C13 120.85(9) . . ? C15 C14 H14 119.6 . . ? C14 C15 H15 119.4 . . ? C14 C15 C16 121.14(9) . . ? C16 C15 H15 119.4 . . ? C15 C16 H16 120.2 . . ? C17 C16 C15 119.60(9) . . ? C17 C16 H16 120.2 . . ? C12 C17 H17 119.7 . . ? C16 C17 C12 120.63(9) . . ? C16 C17 H17 119.7 . . ? 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 C1 1.3707(11) . ? O1 C9 1.3683(11) . ? C1 C2 1.3944(14) . ? C1 C6 1.3885(13) . ? O2 C7 1.2285(11) . ? C2 H2 0.9500 . ? C2 C3 1.3770(16) . ? C3 H3 0.9500 . ? C3 C4 1.3987(16) . ? C4 H4 0.9500 . ? C4 C5 1.3752(14) . ? C5 H5 0.9500 . ? C5 C6 1.4051(13) . ? C6 C7 1.4697(13) . ? C7 C8 1.4723(12) . ? C8 C9 1.3899(12) . ? C8 C13 1.4475(13) . ? C9 C10 1.4128(13) . ? C10 H10 0.9500 . ? C10 C11 1.3561(14) . ? C11 H11 0.9500 . ? C11 C12 1.4230(14) . ? C12 C13 1.4252(12) . ? C12 C17 1.4117(14) . ? C13 C14 1.4154(13) . ? C14 H14 0.9500 . ? C14 C15 1.3762(13) . ? C15 H15 0.9500 . ? C15 C16 1.4020(15) . ? C16 H16 0.9500 . ? C16 C17 1.3698(16) . ? C17 H17 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 _geom_hbond_publ_flag C14 H14 O2 0.95 2.18 2.8415(12) 125.7 . yes C17 H17 O2 0.95 2.41 3.2597(12) 149.4 4_676 yes 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 O1 C1 C2 C3 179.04(8) . . . . ? O1 C1 C6 C5 -179.13(8) . . . . ? O1 C1 C6 C7 1.97(13) . . . . ? O1 C9 C10 C11 179.54(8) . . . . ? C1 O1 C9 C8 -2.67(13) . . . . ? C1 O1 C9 C10 177.65(7) . . . . ? C1 C2 C3 C4 0.31(15) . . . . ? C1 C6 C7 O2 177.44(9) . . . . ? C1 C6 C7 C8 -2.49(13) . . . . ? O2 C7 C8 C9 -179.33(9) . . . . ? O2 C7 C8 C13 1.65(15) . . . . ? C2 C1 C6 C5 0.82(14) . . . . ? C2 C1 C6 C7 -178.09(8) . . . . ? C2 C3 C4 C5 0.34(15) . . . . ? C3 C4 C5 C6 -0.42(15) . . . . ? C4 C5 C6 C1 -0.14(14) . . . . ? C4 C5 C6 C7 178.76(9) . . . . ? C5 C6 C7 O2 -1.43(14) . . . . ? C5 C6 C7 C8 178.63(8) . . . . ? C6 C1 C2 C3 -0.90(14) . . . . ? C6 C7 C8 C9 0.60(12) . . . . ? C6 C7 C8 C13 -178.42(8) . . . . ? C7 C8 C9 O1 1.98(13) . . . . ? C7 C8 C9 C10 -178.37(8) . . . . ? C7 C8 C13 C12 177.81(8) . . . . ? C7 C8 C13 C14 -2.73(14) . . . . ? C8 C9 C10 C11 -0.15(14) . . . . ? C8 C13 C14 C15 179.36(9) . . . . ? C9 O1 C1 C2 -179.34(8) . . . . ? C9 O1 C1 C6 0.60(13) . . . . ? C9 C8 C13 C12 -1.22(12) . . . . ? C9 C8 C13 C14 178.25(8) . . . . ? C9 C10 C11 C12 0.11(14) . . . . ? C10 C11 C12 C13 -0.66(14) . . . . ? C10 C11 C12 C17 179.64(9) . . . . ? C11 C12 C13 C8 1.20(13) . . . . ? C11 C12 C13 C14 -178.29(8) . . . . ? C11 C12 C17 C16 179.25(9) . . . . ? C12 C13 C14 C15 -1.17(13) . . . . ? C13 C8 C9 O1 -178.95(7) . . . . ? C13 C8 C9 C10 0.71(13) . . . . ? C13 C12 C17 C16 -0.45(14) . . . . ? C13 C14 C15 C16 -0.04(15) . . . . ? C14 C15 C16 C17 1.05(16) . . . . ? C15 C16 C17 C12 -0.79(15) . . . . ? C17 C12 C13 C8 -179.09(8) . . . . ? C17 C12 C13 C14 1.41(13) . . . . ?