#------------------------------------------------------------------------------ #$Date: 2020-02-20 07:40:17 +0200 (Thu, 20 Feb 2020) $ #$Revision: 248310 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/73/1557342.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_1557342 loop_ _publ_author_name 'huang, Yue-e' 'Wang, Xing-zhi' 'Hu, Peng' 'Qi, Xinghui' 'Huang, Xiao-ying' 'Kloc, Christian' 'Wu, Xiaohui' 'Du, Kezhao' _publ_section_title ; Single-photon upconversion in 6-pentaceneone crystal from bulk to ultrathin flake ; _journal_name_full Nanoscale _journal_paper_doi 10.1039/D0NR00306A _journal_year 2020 _chemical_formula_moiety 'C22 H14 O' _chemical_formula_sum 'C22 H14 O' _chemical_formula_weight 294.33 _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _atom_sites_solution_hydrogens geom _audit_creation_date 2019-03-28 _audit_creation_method ; Olex2 1.2 (compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324) ; _audit_update_record ; 2019-04-02 deposited with the CCDC. 2020-02-19 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 91.727(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.5602(4) _cell_length_b 14.7939(9) _cell_length_c 14.8216(9) _cell_measurement_reflns_used 2401 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 28.8950 _cell_measurement_theta_min 3.8590 _cell_volume 1437.80(15) _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0373 _diffrn_reflns_av_unetI/netI 0.0435 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 17319 _diffrn_reflns_point_group_measured_fraction_full 0.994 _diffrn_reflns_point_group_measured_fraction_max 0.993 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.019 _diffrn_reflns_theta_min 3.398 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.81274 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour green _exptl_crystal_density_diffrn 1.360 _exptl_crystal_description sheet _exptl_crystal_F_000 616 _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.589 _refine_diff_density_min -0.160 _refine_diff_density_rms 0.041 _refine_ls_abs_structure_details ; Flack x determined using 1009 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.3(10) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 415 _refine_ls_number_reflns 5614 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.034 _refine_ls_R_factor_all 0.1125 _refine_ls_R_factor_gt 0.0588 _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^)+(0.0808P)^2^+0.0199P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1493 _refine_ls_wR_factor_ref 0.1827 _reflns_Friedel_coverage 0.913 _reflns_Friedel_fraction_full 0.991 _reflns_Friedel_fraction_max 0.989 _reflns_number_gt 3097 _reflns_number_total 5614 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0nr00306a2.cif _cod_data_source_block x _cod_database_code 1557342 _shelx_shelxl_version_number 2014/7 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups 2.a Secondary CH2 refined with riding coordinates: C12(H12A,H12B), C34(H34A,H34B) 2.b Aromatic/amide H refined with riding coordinates: C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C14(H14), C16(H16), C17(H17), C18(H18), C19(H19), C21(H21), C25(H25), C27(H27), C28(H28), C29(H29), C30(H30), C32(H32), C36(H36), C38(H38), C39(H39), C40(H40), C41(H41), C43(H43) ; _shelx_res_file ; x.res created by SHELXL-2014/7 TITL DUKE_a.res in P2(1) REM Old TITL DUKE in P2(1)/m REM SHELXT solution in P2(1) REM R1 0.164, Rweak 0.003, Alpha 0.023, Orientation as input REM Flack x = -0.381 ( 1.096 ) from Parsons' quotients REM Formula found by SHELXT: C41 N3 O2 CELL 0.71073 6.5602 14.7939 14.8216 90 91.727 90 ZERR 4 0.0004 0.0009 0.0009 0 0.005 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H O UNIT 88 56 4 L.S. 10 PLAN 20 htab BOND $H LIST 4 fmap 2 acta SHEL 999 0.81 REM REM REM WGHT 0.080800 0.019900 FVAR 0.37504 O1 3 0.458153 0.543994 0.637140 11.00000 0.05155 0.08132 = 0.05582 0.00221 0.01042 -0.02174 C1 1 0.616320 0.581164 0.615702 11.00000 0.03472 0.03564 = 0.04292 0.00168 0.00720 -0.00565 C2 1 0.773826 0.606023 0.685326 11.00000 0.03873 0.03020 = 0.03719 -0.00112 0.00478 0.00414 C3 1 0.735574 0.589723 0.774580 11.00000 0.04342 0.04223 = 0.04466 0.00280 0.00678 -0.00296 AFIX 43 H3 2 0.611514 0.564335 0.789734 11.00000 -1.20000 AFIX 0 C4 1 0.880531 0.610700 0.843607 11.00000 0.05023 0.04165 = 0.03823 0.00477 0.00597 0.00627 C5 1 0.846353 0.593734 0.935657 11.00000 0.06666 0.05999 = 0.04572 -0.00033 0.00861 -0.00338 AFIX 43 H5 2 0.723500 0.568663 0.952906 11.00000 -1.20000 AFIX 0 C6 1 0.992686 0.614017 0.998776 11.00000 0.08023 0.08719 = 0.04170 0.00351 0.00417 -0.00264 AFIX 43 H6 2 0.968891 0.603495 1.059418 11.00000 -1.20000 AFIX 0 C7 1 1.181084 0.650981 0.973531 11.00000 0.07571 0.08527 = 0.04423 0.00571 -0.00674 -0.00914 AFIX 43 H7 2 1.280489 0.664369 1.017570 11.00000 -1.20000 AFIX 0 C8 1 1.217677 0.666991 0.885808 11.00000 0.05245 0.06243 = 0.05434 0.00265 0.00090 -0.00615 AFIX 43 H8 2 1.342973 0.690785 0.870150 11.00000 -1.20000 AFIX 0 C9 1 1.070780 0.648469 0.818136 11.00000 0.04865 0.03587 = 0.03997 0.00005 0.00270 -0.00061 C10 1 1.103770 0.664524 0.725727 11.00000 0.03594 0.04334 = 0.04737 0.00112 0.00589 -0.00316 AFIX 43 H10 2 1.227663 0.688943 0.708974 11.00000 -1.20000 AFIX 0 C11 1 0.961509 0.645576 0.661273 11.00000 0.04046 0.03190 = 0.03568 0.00088 0.00748 0.00244 C12 1 1.008269 0.661845 0.564015 11.00000 0.05039 0.05263 = 0.03807 0.00328 0.00582 0.00098 AFIX 23 H12A 2 1.050358 0.724348 0.557917 11.00000 -1.20000 H12B 2 1.123957 0.624400 0.549230 11.00000 -1.20000 AFIX 0 C13 1 0.841052 0.644094 0.495464 11.00000 0.03501 0.03313 = 0.03865 -0.00099 0.00780 0.00590 C14 1 0.868216 0.664841 0.406766 11.00000 0.04316 0.03772 = 0.04449 0.00581 0.01315 -0.00267 AFIX 43 H14 2 0.988914 0.692450 0.390311 11.00000 -1.20000 AFIX 0 C15 1 0.719091 0.645593 0.340170 11.00000 0.04588 0.03620 = 0.04054 0.00305 0.00773 0.00793 C16 1 0.743260 0.665768 0.247770 11.00000 0.05818 0.04438 = 0.04162 0.00854 0.01032 -0.00135 AFIX 43 H16 2 0.862242 0.693553 0.229428 11.00000 -1.20000 AFIX 0 C17 1 0.595933 0.645151 0.186356 11.00000 0.07033 0.06566 = 0.03456 0.00882 0.00126 0.00372 AFIX 43 H17 2 0.614383 0.658722 0.125881 11.00000 -1.20000 AFIX 0 C18 1 0.415460 0.603649 0.211907 11.00000 0.05948 0.06124 = 0.04576 -0.00225 -0.01014 0.00306 AFIX 43 H18 2 0.315244 0.590542 0.168141 11.00000 -1.20000 AFIX 0 C19 1 0.383731 0.582320 0.298217 11.00000 0.04795 0.04657 = 0.04580 -0.00245 0.00157 -0.00741 AFIX 43 H19 2 0.263577 0.553638 0.313697 11.00000 -1.20000 AFIX 0 C20 1 0.534534 0.603655 0.366448 11.00000 0.04786 0.03488 = 0.04099 -0.00162 -0.00152 0.00503 C21 1 0.508490 0.582168 0.456093 11.00000 0.03245 0.03445 = 0.04643 -0.00047 0.00639 -0.00725 AFIX 43 H21 2 0.389242 0.553440 0.472712 11.00000 -1.20000 AFIX 0 C22 1 0.656121 0.602488 0.521724 11.00000 0.03618 0.03207 = 0.03848 0.00220 0.00000 0.00407 O2 3 1.095223 0.452837 0.434342 11.00000 0.05633 0.07628 = 0.05189 -0.00066 0.00961 -0.01447 C23 1 0.935550 0.416958 0.455398 11.00000 0.03353 0.03582 = 0.04355 -0.00008 0.01245 -0.00323 C24 1 0.901065 0.395860 0.551256 11.00000 0.03356 0.02428 = 0.04599 0.00219 0.01357 -0.00283 C25 1 1.048761 0.414789 0.614802 11.00000 0.03957 0.03858 = 0.04300 0.00038 0.00769 -0.00075 AFIX 43 H25 2 1.169835 0.441090 0.596953 11.00000 -1.20000 AFIX 0 C26 1 1.023455 0.395632 0.707138 11.00000 0.03982 0.02954 = 0.04490 0.00187 0.00845 -0.00275 C27 1 1.173846 0.416579 0.773410 11.00000 0.04925 0.05241 = 0.04257 0.00317 -0.00057 -0.00581 AFIX 43 H27 2 1.294705 0.444033 0.756931 11.00000 -1.20000 AFIX 0 C28 1 1.143076 0.396810 0.861525 11.00000 0.06822 0.06433 = 0.04480 0.00475 -0.00252 -0.00713 AFIX 43 H28 2 1.242642 0.411014 0.905230 11.00000 -1.20000 AFIX 0 C29 1 0.960346 0.354780 0.886803 11.00000 0.07760 0.06336 = 0.04042 0.00415 0.01002 -0.01206 AFIX 43 H29 2 0.941194 0.340743 0.947120 11.00000 -1.20000 AFIX 0 C30 1 0.811603 0.334512 0.823874 11.00000 0.06306 0.05838 = 0.04402 0.00067 0.01067 -0.01367 AFIX 43 H30 2 0.691306 0.307566 0.841795 11.00000 -1.20000 AFIX 0 C31 1 0.838160 0.353891 0.732351 11.00000 0.04261 0.03413 = 0.04510 -0.00209 0.00895 -0.00547 C32 1 0.688658 0.335008 0.664822 11.00000 0.03736 0.03663 = 0.04285 -0.00106 0.01060 -0.00781 AFIX 43 H32 2 0.567273 0.307983 0.681246 11.00000 -1.20000 AFIX 0 C33 1 0.715645 0.354922 0.576435 11.00000 0.03222 0.02762 = 0.04475 -0.00181 0.00868 -0.00699 C34 1 0.550976 0.336356 0.507330 11.00000 0.03647 0.04291 = 0.04522 0.00333 0.00506 -0.00782 AFIX 23 H34A 2 0.513148 0.273209 0.512331 11.00000 -1.20000 H34B 2 0.432690 0.371860 0.522744 11.00000 -1.20000 AFIX 0 C35 1 0.594449 0.354488 0.412357 11.00000 0.03420 0.02927 = 0.04435 0.00045 0.00372 -0.00288 C36 1 0.451022 0.333869 0.345199 11.00000 0.03538 0.03551 = 0.04995 0.00009 0.00658 -0.00714 AFIX 43 H36 2 0.328960 0.307070 0.361048 11.00000 -1.20000 AFIX 0 C37 1 0.483793 0.352034 0.254369 11.00000 0.04115 0.03756 = 0.05905 0.00126 -0.00031 0.00279 C38 1 0.333847 0.332609 0.186470 11.00000 0.05229 0.05742 = 0.04956 0.00026 -0.01054 -0.01020 AFIX 43 H38 2 0.210130 0.306901 0.201639 11.00000 -1.20000 AFIX 0 C39 1 0.371965 0.351750 0.099274 11.00000 0.06502 0.08123 = 0.05509 0.00357 -0.01837 -0.00412 AFIX 43 H39 2 0.273709 0.338172 0.054792 11.00000 -1.20000 AFIX 0 C40 1 0.554560 0.391247 0.074546 11.00000 0.07493 0.07541 = 0.05199 0.01210 -0.00885 -0.01008 AFIX 43 H40 2 0.575498 0.405263 0.014364 11.00000 -1.20000 AFIX 0 C41 1 0.700389 0.409125 0.137408 11.00000 0.05473 0.06447 = 0.04141 0.00399 0.00489 -0.00606 AFIX 43 H41 2 0.823250 0.434066 0.119997 11.00000 -1.20000 AFIX 0 C42 1 0.670691 0.390804 0.229168 11.00000 0.04334 0.03975 = 0.04464 0.00022 0.00607 -0.00098 C43 1 0.814538 0.411222 0.297300 11.00000 0.03952 0.03984 = 0.04000 0.00032 0.00788 0.00175 AFIX 43 H43 2 0.937385 0.437546 0.281824 11.00000 -1.20000 AFIX 0 C44 1 0.780001 0.393461 0.387522 11.00000 0.03748 0.02655 = 0.04508 -0.00066 0.00972 -0.00343 HKLF 4 REM DUKE_a.res in P2(1) REM R1 = 0.0588 for 3097 Fo > 4sig(Fo) and 0.1125 for all 5614 data REM 415 parameters refined using 1 restraints END WGHT 0.0809 0.0205 REM No hydrogen bonds found for HTAB generation REM Highest difference peak 0.589, deepest hole -0.160, 1-sigma level 0.041 Q1 1 1.1556 0.6961 0.5423 11.00000 0.05 0.59 Q2 1 0.3946 0.3049 0.5287 11.00000 0.05 0.40 Q3 1 0.9787 0.4560 0.2783 11.00000 0.05 0.33 Q4 1 0.5811 0.5419 0.7944 11.00000 0.05 0.29 Q5 1 0.2752 0.3061 0.3826 11.00000 0.05 0.28 Q6 1 0.3351 0.5428 0.4840 11.00000 0.05 0.27 Q7 1 1.2175 0.4605 0.5940 11.00000 0.05 0.23 Q8 1 0.7846 0.4214 0.3467 11.00000 0.05 0.17 Q9 1 0.8953 0.4187 0.5072 11.00000 0.05 0.16 Q10 1 0.9121 0.3782 0.7190 11.00000 0.05 0.16 Q11 1 0.6541 0.5799 0.5718 11.00000 0.05 0.16 Q12 1 0.7978 0.3774 0.5637 11.00000 0.05 0.15 Q13 1 0.5044 0.3005 0.6819 11.00000 0.05 0.15 Q14 1 1.2843 0.6940 0.6992 11.00000 0.05 0.15 Q15 1 0.7875 0.5797 0.7207 11.00000 0.05 0.15 Q16 1 1.0419 0.7001 0.3858 11.00000 0.05 0.15 Q17 1 1.0165 0.4201 0.6838 11.00000 0.05 0.13 Q18 1 0.1899 0.2586 0.1573 11.00000 0.05 0.13 Q19 1 0.5683 0.3539 0.4580 11.00000 0.05 0.13 Q20 1 0.9987 0.6397 0.8339 11.00000 0.05 0.13 ; _shelx_res_checksum 24680 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.4582(5) 0.5440(3) 0.6371(2) 0.0627(11) Uani 1 1 d . . . . . C1 C 0.6163(8) 0.5812(3) 0.6157(3) 0.0376(13) Uani 1 1 d . . . . . C2 C 0.7738(7) 0.6060(3) 0.6853(3) 0.0353(12) Uani 1 1 d . . . . . C3 C 0.7356(8) 0.5897(4) 0.7746(3) 0.0433(14) Uani 1 1 d . . . . . H3 H 0.6115 0.5643 0.7897 0.052 Uiso 1 1 calc R . . . . C4 C 0.8805(8) 0.6107(4) 0.8436(3) 0.0433(14) Uani 1 1 d . . . . . C5 C 0.8464(8) 0.5937(4) 0.9357(4) 0.0573(15) Uani 1 1 d . . . . . H5 H 0.7235 0.5687 0.9529 0.069 Uiso 1 1 calc R . . . . C6 C 0.9927(10) 0.6140(4) 0.9988(4) 0.0697(17) Uani 1 1 d . . . . . H6 H 0.9689 0.6035 1.0594 0.084 Uiso 1 1 calc R . . . . C7 C 1.1811(9) 0.6510(4) 0.9735(4) 0.0686(17) Uani 1 1 d . . . . . H7 H 1.2805 0.6644 1.0176 0.082 Uiso 1 1 calc R . . . . C8 C 1.2177(8) 0.6670(4) 0.8858(4) 0.0564(15) Uani 1 1 d . . . . . H8 H 1.3430 0.6908 0.8702 0.068 Uiso 1 1 calc R . . . . C9 C 1.0708(8) 0.6485(3) 0.8181(4) 0.0415(13) Uani 1 1 d . . . . . C10 C 1.1038(7) 0.6645(3) 0.7257(4) 0.0421(14) Uani 1 1 d . . . . . H10 H 1.2277 0.6889 0.7090 0.051 Uiso 1 1 calc R . . . . C11 C 0.9615(7) 0.6456(3) 0.6613(3) 0.0359(13) Uani 1 1 d . . . . . C12 C 1.0083(8) 0.6618(4) 0.5640(3) 0.0469(15) Uani 1 1 d . . . . . H12A H 1.0504 0.7243 0.5579 0.056 Uiso 1 1 calc R . . . . H12B H 1.1240 0.6244 0.5492 0.056 Uiso 1 1 calc R . . . . C13 C 0.8411(7) 0.6441(4) 0.4955(3) 0.0355(13) Uani 1 1 d . . . . . C14 C 0.8682(8) 0.6648(3) 0.4068(4) 0.0416(14) Uani 1 1 d . . . . . H14 H 0.9889 0.6925 0.3903 0.050 Uiso 1 1 calc R . . . . C15 C 0.7191(8) 0.6456(4) 0.3402(4) 0.0407(14) Uani 1 1 d . . . . . C16 C 0.7433(8) 0.6658(4) 0.2478(4) 0.0479(14) Uani 1 1 d . . . . . H16 H 0.8622 0.6936 0.2294 0.057 Uiso 1 1 calc R . . . . C17 C 0.5959(9) 0.6452(4) 0.1864(4) 0.0569(16) Uani 1 1 d . . . . . H17 H 0.6144 0.6587 0.1259 0.068 Uiso 1 1 calc R . . . . C18 C 0.4155(9) 0.6036(4) 0.2119(4) 0.0557(16) Uani 1 1 d . . . . . H18 H 0.3152 0.5905 0.1681 0.067 Uiso 1 1 calc R . . . . C19 C 0.3837(8) 0.5823(4) 0.2982(4) 0.0468(14) Uani 1 1 d . . . . . H19 H 0.2636 0.5536 0.3137 0.056 Uiso 1 1 calc R . . . . C20 C 0.5345(8) 0.6037(4) 0.3664(4) 0.0413(14) Uani 1 1 d . . . . . C21 C 0.5085(7) 0.5822(3) 0.4561(3) 0.0377(13) Uani 1 1 d . . . . . H21 H 0.3892 0.5534 0.4727 0.045 Uiso 1 1 calc R . . . . C22 C 0.6561(8) 0.6025(3) 0.5217(3) 0.0356(12) Uani 1 1 d . . . . . O2 O 1.0952(5) 0.4528(3) 0.4343(2) 0.0613(10) Uani 1 1 d . . . . . C23 C 0.9355(8) 0.4170(4) 0.4554(3) 0.0374(13) Uani 1 1 d . . . . . C24 C 0.9011(7) 0.3959(3) 0.5513(4) 0.0344(12) Uani 1 1 d . . . . . C25 C 1.0488(8) 0.4148(3) 0.6148(3) 0.0403(13) Uani 1 1 d . . . . . H25 H 1.1698 0.4411 0.5970 0.048 Uiso 1 1 calc R . . . . C26 C 1.0235(8) 0.3956(3) 0.7071(3) 0.0379(13) Uani 1 1 d . . . . . C27 C 1.1738(8) 0.4166(3) 0.7734(4) 0.0481(13) Uani 1 1 d . . . . . H27 H 1.2947 0.4440 0.7569 0.058 Uiso 1 1 calc R . . . . C28 C 1.1431(9) 0.3968(4) 0.8615(4) 0.0592(16) Uani 1 1 d . . . . . H28 H 1.2426 0.4110 0.9052 0.071 Uiso 1 1 calc R . . . . C29 C 0.9603(9) 0.3548(4) 0.8868(4) 0.0603(16) Uani 1 1 d . . . . . H29 H 0.9412 0.3407 0.9471 0.072 Uiso 1 1 calc R . . . . C30 C 0.8116(8) 0.3345(4) 0.8239(4) 0.0550(15) Uani 1 1 d . . . . . H30 H 0.6913 0.3076 0.8418 0.066 Uiso 1 1 calc R . . . . C31 C 0.8382(7) 0.3539(3) 0.7324(3) 0.0405(13) Uani 1 1 d . . . . . C32 C 0.6887(7) 0.3350(3) 0.6648(3) 0.0388(13) Uani 1 1 d . . . . . H32 H 0.5673 0.3080 0.6812 0.047 Uiso 1 1 calc R . . . . C33 C 0.7156(7) 0.3549(3) 0.5764(3) 0.0347(13) Uani 1 1 d . . . . . C34 C 0.5510(7) 0.3364(4) 0.5073(3) 0.0415(14) Uani 1 1 d . . . . . H34A H 0.5131 0.2732 0.5123 0.050 Uiso 1 1 calc R . . . . H34B H 0.4327 0.3719 0.5227 0.050 Uiso 1 1 calc R . . . . C35 C 0.5944(7) 0.3545(3) 0.4124(3) 0.0359(13) Uani 1 1 d . . . . . C36 C 0.4510(7) 0.3339(3) 0.3452(4) 0.0402(13) Uani 1 1 d . . . . . H36 H 0.3290 0.3071 0.3610 0.048 Uiso 1 1 calc R . . . . C37 C 0.4838(8) 0.3520(4) 0.2544(4) 0.0460(14) Uani 1 1 d . . . . . C38 C 0.3338(8) 0.3326(4) 0.1865(4) 0.0533(15) Uani 1 1 d . . . . . H38 H 0.2101 0.3069 0.2016 0.064 Uiso 1 1 calc R . . . . C39 C 0.3720(10) 0.3518(5) 0.0993(4) 0.0675(19) Uani 1 1 d . . . . . H39 H 0.2737 0.3382 0.0548 0.081 Uiso 1 1 calc R . . . . C40 C 0.5546(10) 0.3912(5) 0.0745(4) 0.0677(18) Uani 1 1 d . . . . . H40 H 0.5755 0.4053 0.0144 0.081 Uiso 1 1 calc R . . . . C41 C 0.7004(8) 0.4091(4) 0.1374(4) 0.0535(15) Uani 1 1 d . . . . . H41 H 0.8233 0.4341 0.1200 0.064 Uiso 1 1 calc R . . . . C42 C 0.6707(8) 0.3908(4) 0.2292(4) 0.0425(14) Uani 1 1 d . . . . . C43 C 0.8145(8) 0.4112(3) 0.2973(3) 0.0397(14) Uani 1 1 d . . . . . H43 H 0.9374 0.4375 0.2818 0.048 Uiso 1 1 calc R . . . . C44 C 0.7800(7) 0.3935(3) 0.3875(3) 0.0362(13) Uani 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.052(2) 0.081(3) 0.056(2) 0.002(2) 0.0104(17) -0.022(2) C1 0.035(3) 0.036(3) 0.043(3) 0.002(2) 0.007(2) -0.006(2) C2 0.039(3) 0.030(3) 0.037(3) -0.001(2) 0.005(2) 0.004(2) C3 0.043(3) 0.042(3) 0.045(3) 0.003(3) 0.007(2) -0.003(3) C4 0.050(3) 0.042(3) 0.038(3) 0.005(3) 0.006(2) 0.006(3) C5 0.067(4) 0.060(4) 0.046(3) 0.000(3) 0.009(3) -0.003(3) C6 0.080(4) 0.087(5) 0.042(3) 0.004(3) 0.004(3) -0.003(4) C7 0.076(4) 0.085(5) 0.044(4) 0.006(3) -0.007(3) -0.009(4) C8 0.052(3) 0.062(4) 0.054(4) 0.003(3) 0.001(3) -0.006(3) C9 0.049(3) 0.036(3) 0.040(3) 0.000(3) 0.003(3) -0.001(3) C10 0.036(3) 0.043(3) 0.047(3) 0.001(3) 0.006(2) -0.003(3) C11 0.040(3) 0.032(3) 0.036(3) 0.001(2) 0.007(2) 0.002(2) C12 0.050(3) 0.053(4) 0.038(3) 0.003(3) 0.006(2) 0.001(3) C13 0.035(3) 0.033(3) 0.039(3) -0.001(2) 0.008(2) 0.006(2) C14 0.043(3) 0.038(3) 0.044(3) 0.006(3) 0.013(2) -0.003(3) C15 0.046(3) 0.036(3) 0.041(3) 0.003(3) 0.008(3) 0.008(3) C16 0.058(3) 0.044(4) 0.042(3) 0.009(3) 0.010(3) -0.001(3) C17 0.070(4) 0.066(4) 0.035(3) 0.009(3) 0.001(3) 0.004(4) C18 0.059(4) 0.061(4) 0.046(4) -0.002(3) -0.010(3) 0.003(3) C19 0.048(3) 0.047(4) 0.046(3) -0.002(3) 0.002(3) -0.007(3) C20 0.048(3) 0.035(3) 0.041(3) -0.002(3) -0.002(2) 0.005(3) C21 0.032(3) 0.034(3) 0.046(3) 0.000(2) 0.006(2) -0.007(2) C22 0.036(3) 0.032(3) 0.038(3) 0.002(2) 0.000(2) 0.004(2) O2 0.056(2) 0.076(3) 0.052(2) -0.0007(19) 0.0096(18) -0.014(2) C23 0.034(3) 0.036(3) 0.044(3) 0.000(2) 0.012(2) -0.003(3) C24 0.034(3) 0.024(3) 0.046(3) 0.002(2) 0.014(2) -0.003(2) C25 0.040(3) 0.039(3) 0.043(3) 0.000(2) 0.008(2) -0.001(3) C26 0.040(3) 0.030(3) 0.045(3) 0.002(2) 0.008(2) -0.003(3) C27 0.049(3) 0.052(3) 0.043(3) 0.003(3) -0.001(2) -0.006(3) C28 0.068(4) 0.064(4) 0.045(4) 0.005(3) -0.003(3) -0.007(3) C29 0.078(4) 0.063(4) 0.040(3) 0.004(3) 0.010(3) -0.012(3) C30 0.063(4) 0.058(4) 0.044(3) 0.001(3) 0.011(3) -0.014(3) C31 0.043(3) 0.034(3) 0.045(3) -0.002(3) 0.009(3) -0.005(3) C32 0.037(3) 0.037(3) 0.043(3) -0.001(3) 0.011(2) -0.008(3) C33 0.032(3) 0.028(3) 0.045(3) -0.002(2) 0.009(2) -0.007(2) C34 0.036(3) 0.043(4) 0.045(3) 0.003(3) 0.005(2) -0.008(3) C35 0.034(3) 0.029(3) 0.044(3) 0.000(2) 0.004(2) -0.003(2) C36 0.035(3) 0.036(3) 0.050(3) 0.000(3) 0.007(2) -0.007(2) C37 0.041(3) 0.038(3) 0.059(4) 0.001(3) 0.000(3) 0.003(3) C38 0.052(3) 0.057(4) 0.050(4) 0.000(3) -0.011(3) -0.010(3) C39 0.065(4) 0.081(5) 0.055(4) 0.004(4) -0.018(3) -0.004(4) C40 0.075(4) 0.075(5) 0.052(4) 0.012(3) -0.009(3) -0.010(4) C41 0.055(4) 0.064(4) 0.041(3) 0.004(3) 0.005(3) -0.006(3) C42 0.043(3) 0.040(3) 0.045(3) 0.000(3) 0.006(3) -0.001(3) C43 0.040(3) 0.040(3) 0.040(3) 0.000(2) 0.008(2) 0.002(2) C44 0.037(3) 0.027(3) 0.045(3) -0.001(2) 0.010(2) -0.003(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 O1 C1 C2 120.6(5) . . ? O1 C1 C22 121.5(4) . . ? C22 C1 C2 118.0(5) . . ? C3 C2 C1 118.8(5) . . ? C3 C2 C11 119.9(5) . . ? C11 C2 C1 121.3(5) . . ? C2 C3 H3 119.3 . . ? C2 C3 C4 121.4(5) . . ? C4 C3 H3 119.3 . . ? C3 C4 C5 122.6(5) . . ? C3 C4 C9 118.0(5) . . ? C5 C4 C9 119.4(5) . . ? C4 C5 H5 120.1 . . ? C6 C5 C4 119.9(6) . . ? C6 C5 H5 120.1 . . ? C5 C6 H6 119.6 . . ? C5 C6 C7 120.7(6) . . ? C7 C6 H6 119.6 . . ? C6 C7 H7 119.8 . . ? C8 C7 C6 120.4(6) . . ? C8 C7 H7 119.8 . . ? C7 C8 H8 119.4 . . ? C7 C8 C9 121.2(6) . . ? C9 C8 H8 119.4 . . ? C8 C9 C4 118.4(5) . . ? C8 C9 C10 122.7(5) . . ? C10 C9 C4 118.8(5) . . ? C9 C10 H10 119.0 . . ? C11 C10 C9 122.0(5) . . ? C11 C10 H10 119.0 . . ? C2 C11 C12 120.7(5) . . ? C10 C11 C2 119.8(5) . . ? C10 C11 C12 119.4(5) . . ? C11 C12 H12A 108.0 . . ? C11 C12 H12B 108.0 . . ? H12A C12 H12B 107.2 . . ? C13 C12 C11 117.2(5) . . ? C13 C12 H12A 108.0 . . ? C13 C12 H12B 108.0 . . ? C14 C13 C12 120.0(5) . . ? C14 C13 C22 119.8(5) . . ? C22 C13 C12 120.2(4) . . ? C13 C14 H14 119.2 . . ? C13 C14 C15 121.6(5) . . ? C15 C14 H14 119.2 . . ? C14 C15 C16 122.9(5) . . ? C14 C15 C20 118.6(5) . . ? C16 C15 C20 118.5(5) . . ? C15 C16 H16 119.7 . . ? C17 C16 C15 120.6(5) . . ? C17 C16 H16 119.7 . . ? C16 C17 H17 119.5 . . ? C16 C17 C18 121.0(5) . . ? C18 C17 H17 119.5 . . ? C17 C18 H18 119.3 . . ? C19 C18 C17 121.3(5) . . ? C19 C18 H18 119.3 . . ? C18 C19 H19 120.0 . . ? C18 C19 C20 120.0(5) . . ? C20 C19 H19 120.0 . . ? C15 C20 C19 118.6(5) . . ? C21 C20 C15 119.6(5) . . ? C21 C20 C19 121.8(5) . . ? C20 C21 H21 119.3 . . ? C20 C21 C22 121.4(5) . . ? C22 C21 H21 119.3 . . ? C13 C22 C1 122.2(4) . . ? C21 C22 C1 118.8(5) . . ? C21 C22 C13 119.0(5) . . ? O2 C23 C24 119.6(5) . . ? O2 C23 C44 121.1(5) . . ? C44 C23 C24 119.3(5) . . ? C25 C24 C23 119.7(5) . . ? C25 C24 C33 120.3(5) . . ? C33 C24 C23 120.0(4) . . ? C24 C25 H25 119.1 . . ? C24 C25 C26 121.9(5) . . ? C26 C25 H25 119.1 . . ? C25 C26 C31 117.9(4) . . ? C27 C26 C25 122.2(5) . . ? C27 C26 C31 119.9(5) . . ? C26 C27 H27 119.9 . . ? C28 C27 C26 120.2(5) . . ? C28 C27 H27 119.9 . . ? C27 C28 H28 119.9 . . ? C27 C28 C29 120.1(5) . . ? C29 C28 H28 119.9 . . ? C28 C29 H29 119.6 . . ? C30 C29 C28 120.8(5) . . ? C30 C29 H29 119.6 . . ? C29 C30 H30 119.7 . . ? C29 C30 C31 120.6(5) . . ? C31 C30 H30 119.7 . . ? C30 C31 C26 118.3(4) . . ? C30 C31 C32 122.9(5) . . ? C32 C31 C26 118.8(5) . . ? C31 C32 H32 118.9 . . ? C33 C32 C31 122.3(5) . . ? C33 C32 H32 118.9 . . ? C24 C33 C34 120.5(5) . . ? C32 C33 C24 118.9(4) . . ? C32 C33 C34 120.6(5) . . ? C33 C34 H34A 107.8 . . ? C33 C34 H34B 107.8 . . ? H34A C34 H34B 107.2 . . ? C35 C34 C33 117.8(5) . . ? C35 C34 H34A 107.8 . . ? C35 C34 H34B 107.8 . . ? C36 C35 C34 120.1(5) . . ? C36 C35 C44 118.5(5) . . ? C44 C35 C34 121.4(4) . . ? C35 C36 H36 119.0 . . ? C35 C36 C37 122.0(5) . . ? C37 C36 H36 119.0 . . ? C36 C37 C38 121.5(5) . . ? C36 C37 C42 119.5(5) . . ? C42 C37 C38 119.0(5) . . ? C37 C38 H38 120.3 . . ? C39 C38 C37 119.5(6) . . ? C39 C38 H38 120.3 . . ? C38 C39 H39 119.2 . . ? C38 C39 C40 121.6(6) . . ? C40 C39 H39 119.2 . . ? C39 C40 H40 120.0 . . ? C41 C40 C39 120.1(6) . . ? C41 C40 H40 120.0 . . ? C40 C41 H41 119.4 . . ? C40 C41 C42 121.1(6) . . ? C42 C41 H41 119.4 . . ? C41 C42 C37 118.7(5) . . ? C43 C42 C37 118.0(5) . . ? C43 C42 C41 123.3(5) . . ? C42 C43 H43 119.0 . . ? C44 C43 C42 122.0(5) . . ? C44 C43 H43 119.0 . . ? C35 C44 C23 120.8(5) . . ? C43 C44 C23 119.3(5) . . ? C43 C44 C35 119.8(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 O1 C1 1.225(6) . ? C1 C2 1.484(7) . ? C1 C22 1.459(7) . ? C2 C3 1.375(6) . ? C2 C11 1.418(6) . ? C3 H3 0.9300 . ? C3 C4 1.410(7) . ? C4 C5 1.412(7) . ? C4 C9 1.429(7) . ? C5 H5 0.9300 . ? C5 C6 1.354(7) . ? C6 H6 0.9300 . ? C6 C7 1.412(8) . ? C7 H7 0.9300 . ? C7 C8 1.350(7) . ? C8 H8 0.9300 . ? C8 C9 1.397(7) . ? C9 C10 1.413(7) . ? C10 H10 0.9300 . ? C10 C11 1.345(7) . ? C11 C12 1.502(7) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C12 C13 1.496(6) . ? C13 C14 1.367(7) . ? C13 C22 1.425(7) . ? C14 H14 0.9300 . ? C14 C15 1.398(7) . ? C15 C16 1.415(7) . ? C15 C20 1.425(7) . ? C16 H16 0.9300 . ? C16 C17 1.343(7) . ? C17 H17 0.9300 . ? C17 C18 1.396(7) . ? C18 H18 0.9300 . ? C18 C19 1.340(7) . ? C19 H19 0.9300 . ? C19 C20 1.429(7) . ? C20 C21 1.382(6) . ? C21 H21 0.9300 . ? C21 C22 1.385(6) . ? O2 C23 1.223(6) . ? C23 C24 1.479(7) . ? C23 C44 1.453(7) . ? C24 C25 1.360(6) . ? C24 C33 1.419(6) . ? C25 H25 0.9300 . ? C25 C26 1.412(6) . ? C26 C27 1.406(6) . ? C26 C31 1.423(6) . ? C27 H27 0.9300 . ? C27 C28 1.359(7) . ? C28 H28 0.9300 . ? C28 C29 1.411(7) . ? C29 H29 0.9300 . ? C29 C30 1.363(6) . ? C30 H30 0.9300 . ? C30 C31 1.402(6) . ? C31 C32 1.408(6) . ? C32 H32 0.9300 . ? C32 C33 1.360(6) . ? C33 C34 1.492(6) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C34 C35 1.469(7) . ? C35 C36 1.383(6) . ? C35 C44 1.406(6) . ? C36 H36 0.9300 . ? C36 C37 1.396(7) . ? C37 C38 1.415(7) . ? C37 C42 1.414(7) . ? C38 H38 0.9300 . ? C38 C39 1.354(7) . ? C39 H39 0.9300 . ? C39 C40 1.392(9) . ? C40 H40 0.9300 . ? C40 C41 1.341(7) . ? C41 H41 0.9300 . ? C41 C42 1.406(7) . ? C42 C43 1.394(7) . ? C43 H43 0.9300 . ? C43 C44 1.388(6) . ?