# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full J.Mater.Chem. _journal_coden_cambridge 1145 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Ching-Ting Chien' _publ_contact_author_email kmunchu@chem.sinica.edu.tw loop_ _publ_author_name 'Ching-Ting Chien' C.-C.Lin M.Watanabe Y.-D.Lin T.-H.Chao T.-c.Chiang ; X.-H.Huang ; Yu.Wen C.-H.Tu C.-H.Sun T.Chow data_i12159 _database_code_depnum_ccdc_archive 'CCDC 847352' #TrackingRef '7494_web_deposit_cif_file_0_Ching-TingChien_1317892119.CCDC-cif.txt' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C66 H54 O6' _chemical_formula_sum 'C66 H54 O6' _chemical_formula_weight 943.09 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.3679(10) _cell_length_b 12.3365(9) _cell_length_c 27.768(2) _cell_angle_alpha 90 _cell_angle_beta 101.536(4) _cell_angle_gamma 90 _cell_volume 4822.5(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100.00(10) _cell_measurement_reflns_used 6594 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 24.83 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description PRISM _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.299 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1992 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Bruker SADABS, 1996' _exptl_absorpt_correction_T_min 0.6749 _exptl_absorpt_correction_T_max 0.7454 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100.00(10) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_av_R_equivalents 0.0385 _diffrn_reflns_av_unetI/netI 0.0662 _diffrn_reflns_number 36505 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.45 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 9863 _reflns_number_gt 5885 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0727P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0008(2) _refine_ls_number_reflns 9863 _refine_ls_number_parameters 656 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1029 _refine_ls_R_factor_gt 0.0515 _refine_ls_wR_factor_ref 0.1477 _refine_ls_wR_factor_gt 0.1173 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.31 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.068 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.06410(11) -0.23219(11) 0.17887(5) 0.0374(4) Uani 1 1 d . . . O2 O -0.00799(10) 0.19356(10) 0.16572(5) 0.0285(4) Uani 1 1 d . . . C1 C -0.20600(14) 0.05689(17) 0.28107(7) 0.0257(5) Uani 1 1 d . . . H1 H -0.2152 0.1315 0.2799 0.031 Uiso 1 1 calc R . . C2 C -0.26934(15) -0.01146(17) 0.29745(8) 0.0298(5) Uani 1 1 d . . . H2 H -0.3212 0.0179 0.3082 0.036 Uiso 1 1 calc R . . C3 C -0.25680(15) -0.12345(18) 0.29814(7) 0.0307(5) Uani 1 1 d . . . H3 H -0.3009 -0.1679 0.3088 0.037 Uiso 1 1 calc R . . C4 C -0.17948(14) -0.16931(17) 0.28308(7) 0.0266(5) Uani 1 1 d . . . H4 H -0.171 -0.2441 0.2834 0.032 Uiso 1 1 calc R . . C4A C -0.11499(14) -0.10093(16) 0.26747(7) 0.0222(5) Uani 1 1 d . . . C5 C -0.02408(13) -0.12302(15) 0.24967(7) 0.0204(5) Uani 1 1 d . . . H5 H 0.0071 -0.1924 0.2597 0.025 Uiso 1 1 calc R . . C5A C -0.04409(14) -0.09802(15) 0.19315(7) 0.0201(5) Uani 1 1 d . . . H5A H -0.1029 -0.1347 0.1775 0.024 Uiso 1 1 calc R . . C6 C 0.03560(14) -0.13914(16) 0.17054(7) 0.0229(5) Uani 1 1 d . . . C6A C 0.07780(13) -0.06895(15) 0.13756(7) 0.0193(5) Uani 1 1 d . . . C7 C 0.13325(14) -0.11621(16) 0.10745(7) 0.0242(5) Uani 1 1 d . . . H7 H 0.1436 -0.1907 0.1086 0.029 Uiso 1 1 calc R . . C8 C 0.17279(14) -0.05265(16) 0.07598(7) 0.0255(5) Uani 1 1 d . . . H8 H 0.2079 -0.0847 0.0551 0.031 Uiso 1 1 calc R . . C9 C 0.16053(14) 0.05862(16) 0.07534(7) 0.0256(5) Uani 1 1 d . . . H9 H 0.1886 0.1012 0.0545 0.031 Uiso 1 1 calc R . . C10 C 0.10686(13) 0.10653(16) 0.10541(7) 0.0224(5) Uani 1 1 d . . . H10 H 0.0998 0.1815 0.1053 0.027 Uiso 1 1 calc R . . C10A C 0.06317(13) 0.04317(15) 0.13592(7) 0.0188(5) Uani 1 1 d . . . C11 C -0.00082(13) 0.09523(16) 0.16482(7) 0.0201(5) Uani 1 1 d . . . C11A C -0.06174(14) 0.02666(14) 0.19119(7) 0.0196(5) Uani 1 1 d . . . H11A H -0.1285 0.0395 0.176 0.023 Uiso 1 1 calc R . . C12 C -0.04652(13) 0.05887(15) 0.24688(7) 0.0197(5) Uani 1 1 d . . . H12 H -0.0329 0.1355 0.2545 0.024 Uiso 1 1 calc R . . C12A C -0.12807(14) 0.01037(15) 0.26639(7) 0.0210(5) Uani 1 1 d . . . C13 C 0.03201(15) -0.02160(15) 0.26847(7) 0.0220(5) Uani 1 1 d . . . C14 C 0.11904(15) -0.00872(16) 0.29500(7) 0.0262(5) Uani 1 1 d . . . C15 C 0.18218(15) -0.10297(18) 0.31302(8) 0.0384(6) Uani 1 1 d . . . H15A H 0.1542 -0.1683 0.2978 0.058 Uiso 1 1 calc R . . H15B H 0.1896 -0.1088 0.348 0.058 Uiso 1 1 calc R . . H15C H 0.2432 -0.0922 0.3047 0.058 Uiso 1 1 calc R . . C16 C 0.15933(15) 0.10075(17) 0.31102(8) 0.0376(6) Uani 1 1 d . . . H16A H 0.116 0.1561 0.2961 0.056 Uiso 1 1 calc R . . H16B H 0.2191 0.1098 0.3011 0.056 Uiso 1 1 calc R . . H16C H 0.1686 0.1064 0.3461 0.056 Uiso 1 1 calc R . . O3 O 0.40121(10) 0.27301(11) 0.30138(5) 0.0322(4) Uani 1 1 d . . . O4 O 0.40947(11) 0.69497(12) 0.29299(5) 0.0407(4) Uani 1 1 d . . . C17 C 0.21831(14) 0.61752(16) 0.42839(7) 0.0251(5) Uani 1 1 d . . . H17 H 0.2214 0.6928 0.4279 0.03 Uiso 1 1 calc R . . C18 C 0.14642(15) 0.56478(17) 0.44614(7) 0.0282(5) Uani 1 1 d . . . H18 H 0.1016 0.6053 0.4582 0.034 Uiso 1 1 calc R . . C19 C 0.14088(15) 0.45279(17) 0.44600(7) 0.0275(5) Uani 1 1 d . . . H19 H 0.0922 0.4191 0.458 0.033 Uiso 1 1 calc R . . C20 C 0.20677(14) 0.38978(16) 0.42826(7) 0.0229(5) Uani 1 1 d . . . H20 H 0.2022 0.3146 0.4276 0.028 Uiso 1 1 calc R . . C20A C 0.27949(14) 0.44230(16) 0.41165(7) 0.0217(5) Uani 1 1 d . . . C21 C 0.36282(13) 0.40078(16) 0.39154(7) 0.0212(5) Uani 1 1 d . . . H21 H 0.3826 0.3261 0.4003 0.025 Uiso 1 1 calc R . . C21A C 0.34190(14) 0.42841(15) 0.33494(7) 0.0217(5) Uani 1 1 d . . . H21A H 0.2777 0.4043 0.3198 0.026 Uiso 1 1 calc R . . C22 C 0.41381(14) 0.36846(17) 0.31206(7) 0.0236(5) Uani 1 1 d . . . C22A C 0.50187(14) 0.42545(17) 0.30617(7) 0.0254(5) Uani 1 1 d . . . C23 C 0.58078(15) 0.36586(19) 0.30012(7) 0.0324(6) Uani 1 1 d . . . H23 H 0.5781 0.2905 0.2994 0.039 Uiso 1 1 calc R . . C24 C 0.66303(16) 0.4184(2) 0.29519(8) 0.0426(7) Uani 1 1 d . . . H24 H 0.7165 0.3784 0.2922 0.051 Uiso 1 1 calc R . . C25 C 0.66635(17) 0.5300(2) 0.29464(8) 0.0438(7) Uani 1 1 d . . . H25 H 0.7223 0.565 0.2917 0.053 Uiso 1 1 calc R . . C26 C 0.58728(16) 0.5902(2) 0.29836(7) 0.0373(6) Uani 1 1 d . . . H26 H 0.589 0.6654 0.2964 0.045 Uiso 1 1 calc R . . C26A C 0.50473(15) 0.53802(17) 0.30513(7) 0.0271(5) Uani 1 1 d . . . C27 C 0.41925(15) 0.60311(18) 0.30880(7) 0.0271(5) Uani 1 1 d . . . C27A C 0.34640(14) 0.55434(15) 0.33450(7) 0.0217(5) Uani 1 1 d . . . H27A H 0.2835 0.5833 0.32 0.026 Uiso 1 1 calc R . . C28 C 0.37142(13) 0.58381(16) 0.39095(7) 0.0222(5) Uani 1 1 d . . . H30 H 0.3981 0.6562 0.3991 0.027 Uiso 1 1 calc R . . C28A C 0.28493(14) 0.55523(16) 0.41152(7) 0.0217(5) Uani 1 1 d . . . C29 C 0.43507(14) 0.48873(15) 0.41072(7) 0.0218(5) Uani 1 1 d . . . C30 C 0.52369(15) 0.48435(15) 0.43582(7) 0.0243(5) Uani 1 1 d . . . C31 C 0.57263(14) 0.37856(16) 0.45093(8) 0.0342(6) Uani 1 1 d . . . H31A H 0.5272 0.3207 0.4449 0.051 Uiso 1 1 calc R . . H31B H 0.6008 0.3808 0.4853 0.051 Uiso 1 1 calc R . . H31C H 0.6212 0.3666 0.4323 0.051 Uiso 1 1 calc R . . C32 C 0.58349(14) 0.58393(16) 0.44979(8) 0.0333(6) Uani 1 1 d . . . H32A H 0.6323 0.5871 0.4307 0.05 Uiso 1 1 calc R . . H32B H 0.6122 0.5809 0.4841 0.05 Uiso 1 1 calc R . . H32C H 0.5442 0.6473 0.4435 0.05 Uiso 1 1 calc R . . O5 O 0.13257(10) 0.28162(11) 0.01788(5) 0.0333(4) Uani 1 1 d . . . O6 O 0.15046(10) 0.71568(11) 0.01939(5) 0.0325(4) Uani 1 1 d . . . C33 C 0.45317(14) 0.59739(17) 0.13274(7) 0.0254(5) Uani 1 1 d . . . H33 H 0.4552 0.6727 0.1331 0.03 Uiso 1 1 calc R . . C34 C 0.51064(14) 0.53744(17) 0.16940(8) 0.0294(5) Uani 1 1 d . . . H34 H 0.5528 0.5729 0.1942 0.035 Uiso 1 1 calc R . . C35 C 0.50584(14) 0.42561(18) 0.16943(7) 0.0288(5) Uani 1 1 d . . . H35 H 0.5446 0.3868 0.1944 0.035 Uiso 1 1 calc R . . C36 C 0.44386(14) 0.37001(17) 0.13270(7) 0.0249(5) Uani 1 1 d . . . H36 H 0.4399 0.2948 0.1331 0.03 Uiso 1 1 calc R . . C36A C 0.38878(14) 0.42962(16) 0.09584(7) 0.0227(5) Uani 1 1 d . . . C37 C 0.31956(13) 0.39764(16) 0.04949(7) 0.0225(5) Uani 1 1 d . . . H37 H 0.3258 0.3237 0.0377 0.027 Uiso 1 1 calc R . . C37A C 0.21718(13) 0.43171(15) 0.05663(7) 0.0204(5) Uani 1 1 d . . . H37A H 0.2074 0.4058 0.0886 0.024 Uiso 1 1 calc R . . C38 C 0.14602(13) 0.37932(16) 0.01642(7) 0.0228(5) Uani 1 1 d . . . C38A C 0.09685(13) 0.44402(16) -0.02607(7) 0.0209(5) Uani 1 1 d . . . C39 C 0.04287(13) 0.39101(16) -0.06654(7) 0.0235(5) Uani 1 1 d . . . H39 H 0.0386 0.3158 -0.0667 0.028 Uiso 1 1 calc R . . C40 C -0.00429(14) 0.44978(16) -0.10642(7) 0.0265(5) Uani 1 1 d . . . H40 H -0.0401 0.4141 -0.1334 0.032 Uiso 1 1 calc R . . C41 C 0.00179(14) 0.56187(16) -0.10615(7) 0.0270(5) Uani 1 1 d . . . H41 H -0.0295 0.6012 -0.1331 0.032 Uiso 1 1 calc R . . C42 C 0.05383(13) 0.61533(16) -0.06623(7) 0.0244(5) Uani 1 1 d . . . H42 H 0.0568 0.6906 -0.0662 0.029 Uiso 1 1 calc R . . C42A C 0.10203(13) 0.55738(15) -0.02586(7) 0.0204(5) Uani 1 1 d . . . C43 C 0.15583(13) 0.61700(16) 0.01717(7) 0.0221(5) Uani 1 1 d . . . C43A C 0.22232(13) 0.55768(15) 0.05710(7) 0.0212(5) Uani 1 1 d . . . H43A H 0.2145 0.5848 0.0892 0.025 Uiso 1 1 calc R . . C44 C 0.32657(13) 0.58101(16) 0.05008(7) 0.0221(5) Uani 1 1 d . . . H44 H 0.3385 0.654 0.0387 0.027 Uiso 1 1 calc R . . C44A C 0.39311(14) 0.54256(16) 0.09591(7) 0.0226(5) Uani 1 1 d . . . C45 C 0.33839(14) 0.48844(15) 0.01568(7) 0.0220(5) Uani 1 1 d . . . C46 C 0.35949(14) 0.48803(16) -0.02878(8) 0.0247(5) Uani 1 1 d . . . C47 C 0.36961(16) 0.38439(17) -0.05563(8) 0.0375(6) Uani 1 1 d . . . H47A H 0.434 0.377 -0.0599 0.056 Uiso 1 1 calc R . . H47B H 0.3276 0.3857 -0.0872 0.056 Uiso 1 1 calc R . . H47C H 0.3537 0.3242 -0.0369 0.056 Uiso 1 1 calc R . . C48 C 0.37787(15) 0.58987(17) -0.05486(8) 0.0355(6) Uani 1 1 d . . . H48A H 0.3677 0.6516 -0.0355 0.053 Uiso 1 1 calc R . . H48B H 0.3354 0.5932 -0.0863 0.053 Uiso 1 1 calc R . . H48C H 0.4423 0.5899 -0.0595 0.053 Uiso 1 1 calc R . . 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 0.0561(11) 0.0233(9) 0.0408(10) 0.0060(7) 0.0289(8) 0.0088(8) O2 0.0405(10) 0.0198(8) 0.0268(8) 0.0006(7) 0.0107(7) 0.0005(7) C1 0.0254(12) 0.0317(13) 0.0190(11) -0.0017(10) 0.0024(9) 0.0022(10) C2 0.0230(12) 0.0471(15) 0.0207(12) -0.0049(11) 0.0074(10) 0.0022(11) C3 0.0283(13) 0.0427(15) 0.0229(12) -0.0038(11) 0.0094(10) -0.0096(11) C4 0.0302(13) 0.0281(12) 0.0216(12) -0.0043(10) 0.0055(10) -0.0074(10) C4A 0.0238(12) 0.0293(12) 0.0125(11) -0.0035(10) 0.0017(9) 0.0000(10) C5 0.0257(12) 0.0190(11) 0.0178(11) 0.0012(9) 0.0072(9) 0.0010(9) C5A 0.0241(12) 0.0204(11) 0.0164(11) 0.0000(9) 0.0052(9) -0.0021(9) C6 0.0307(13) 0.0195(11) 0.0189(11) -0.0025(10) 0.0058(9) 0.0013(10) C6A 0.0178(11) 0.0244(12) 0.0148(11) -0.0021(9) 0.0010(9) -0.0024(9) C7 0.0266(12) 0.0248(12) 0.0213(12) -0.0012(10) 0.0050(9) 0.0007(10) C8 0.0232(12) 0.0321(13) 0.0228(12) 0.0022(10) 0.0086(9) 0.0043(10) C9 0.0230(12) 0.0319(13) 0.0236(12) 0.0061(10) 0.0085(9) 0.0001(10) C10 0.0234(12) 0.0219(11) 0.0218(11) 0.0044(10) 0.0041(9) 0.0012(9) C10A 0.0191(11) 0.0192(11) 0.0169(11) -0.0020(9) 0.0008(9) 0.0003(9) C11 0.0237(12) 0.0215(12) 0.0137(11) 0.0021(10) 0.0008(9) -0.0001(9) C11A 0.0192(11) 0.0211(11) 0.0182(11) -0.0014(9) 0.0033(9) 0.0019(9) C12 0.0241(12) 0.0186(11) 0.0169(11) -0.0023(9) 0.0051(9) -0.0001(9) C12A 0.0201(11) 0.0283(12) 0.0135(11) -0.0021(9) 0.0005(9) -0.0022(9) C13 0.0242(12) 0.0295(12) 0.0144(11) -0.0003(9) 0.0084(9) 0.0001(10) C14 0.0255(12) 0.0327(13) 0.0210(12) 0.0020(10) 0.0061(10) -0.0017(10) C15 0.0277(13) 0.0521(16) 0.0337(14) 0.0102(12) 0.0024(11) 0.0055(12) C16 0.0357(14) 0.0468(15) 0.0300(13) -0.0014(12) 0.0059(11) -0.0103(12) O3 0.0370(10) 0.0281(9) 0.0315(9) -0.0032(7) 0.0068(7) 0.0028(7) O4 0.0550(11) 0.0284(9) 0.0406(10) 0.0073(8) 0.0138(8) -0.0062(8) C17 0.0273(13) 0.0260(12) 0.0204(12) -0.0021(10) 0.0010(10) 0.0021(10) C18 0.0233(12) 0.0406(14) 0.0199(12) -0.0026(11) 0.0027(9) 0.0021(11) C19 0.0231(12) 0.0405(14) 0.0186(12) 0.0030(11) 0.0037(9) -0.0010(11) C20 0.0241(12) 0.0256(12) 0.0167(11) 0.0005(9) -0.0016(9) -0.0031(10) C20A 0.0194(11) 0.0289(12) 0.0149(11) 0.0005(10) -0.0010(9) -0.0028(10) C21 0.0213(11) 0.0227(11) 0.0190(11) 0.0042(9) 0.0024(9) 0.0012(9) C21A 0.0200(11) 0.0249(12) 0.0188(11) 0.0028(10) 0.0008(9) -0.0015(9) C22 0.0244(12) 0.0298(13) 0.0151(11) 0.0017(10) 0.0001(9) 0.0015(10) C22A 0.0245(12) 0.0373(13) 0.0142(11) 0.0011(10) 0.0037(9) -0.0005(11) C23 0.0305(14) 0.0500(15) 0.0173(12) 0.0010(11) 0.0063(10) 0.0034(12) C24 0.0262(14) 0.082(2) 0.0200(13) -0.0036(14) 0.0060(10) -0.0001(14) C25 0.0293(15) 0.079(2) 0.0239(13) -0.0088(14) 0.0081(11) -0.0221(14) C26 0.0388(15) 0.0530(15) 0.0218(13) -0.0063(12) 0.0101(11) -0.0177(13) C26A 0.0283(13) 0.0403(14) 0.0133(11) -0.0012(10) 0.0059(9) -0.0076(11) C27 0.0332(14) 0.0292(13) 0.0177(12) -0.0003(10) 0.0025(10) -0.0090(11) C27A 0.0228(12) 0.0238(11) 0.0173(11) 0.0011(10) 0.0014(9) -0.0011(9) C28 0.0239(12) 0.0214(11) 0.0200(11) -0.0025(10) 0.0011(9) -0.0043(9) C28A 0.0209(12) 0.0262(12) 0.0154(11) 0.0014(10) -0.0023(9) -0.0024(10) C29 0.0241(12) 0.0268(12) 0.0151(11) 0.0007(9) 0.0053(9) -0.0026(10) C30 0.0229(12) 0.0332(13) 0.0170(11) 0.0002(10) 0.0040(9) -0.0028(10) C31 0.0254(13) 0.0419(14) 0.0329(13) 0.0030(11) 0.0003(10) 0.0037(11) C32 0.0256(13) 0.0439(14) 0.0281(13) -0.0012(11) 0.0001(10) -0.0060(11) O5 0.0359(10) 0.0238(8) 0.0370(9) 0.0029(7) -0.0002(7) -0.0047(7) O6 0.0395(10) 0.0232(8) 0.0329(9) -0.0031(7) 0.0027(7) 0.0027(7) C33 0.0282(12) 0.0304(12) 0.0197(12) 0.0000(10) 0.0096(10) -0.0040(10) C34 0.0244(13) 0.0429(14) 0.0205(12) -0.0025(11) 0.0039(10) -0.0068(11) C35 0.0247(12) 0.0434(14) 0.0188(12) 0.0051(11) 0.0057(10) 0.0059(11) C36 0.0249(12) 0.0302(12) 0.0213(12) 0.0034(10) 0.0087(10) 0.0026(10) C36A 0.0222(12) 0.0272(12) 0.0205(12) -0.0009(10) 0.0085(9) 0.0005(10) C37 0.0242(12) 0.0227(11) 0.0214(11) -0.0007(10) 0.0062(9) 0.0017(9) C37A 0.0221(12) 0.0225(11) 0.0174(11) 0.0036(9) 0.0061(9) 0.0005(9) C38 0.0222(12) 0.0239(12) 0.0244(12) 0.0023(10) 0.0093(9) 0.0019(10) C38A 0.0189(11) 0.0228(11) 0.0226(12) 0.0010(10) 0.0078(9) 0.0010(9) C39 0.0237(12) 0.0240(12) 0.0234(12) -0.0020(10) 0.0064(9) -0.0002(9) C40 0.0255(12) 0.0326(13) 0.0207(12) -0.0056(11) 0.0027(10) -0.0003(10) C41 0.0292(13) 0.0320(13) 0.0194(12) 0.0053(10) 0.0040(10) 0.0063(10) C42 0.0241(12) 0.0238(12) 0.0266(12) 0.0017(10) 0.0082(10) 0.0023(10) C42A 0.0183(11) 0.0218(11) 0.0223(12) 0.0003(10) 0.0069(9) 0.0005(9) C43 0.0218(12) 0.0221(12) 0.0251(12) 0.0000(10) 0.0109(9) -0.0005(9) C43A 0.0247(12) 0.0207(11) 0.0200(11) -0.0012(9) 0.0089(9) -0.0004(9) C44 0.0230(12) 0.0227(11) 0.0215(11) 0.0018(10) 0.0065(9) -0.0056(9) C44A 0.0213(12) 0.0304(12) 0.0174(11) 0.0003(10) 0.0068(9) -0.0022(10) C45 0.0174(11) 0.0293(12) 0.0194(11) 0.0009(10) 0.0044(9) 0.0000(9) C46 0.0192(12) 0.0327(13) 0.0228(12) -0.0010(10) 0.0056(9) 0.0015(9) C47 0.0392(14) 0.0462(15) 0.0295(13) -0.0042(12) 0.0125(11) 0.0020(12) C48 0.0347(14) 0.0463(15) 0.0279(13) 0.0054(12) 0.0119(11) 0.0001(12) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C6 1.225(2) . ? O2 C11 1.218(2) . ? C1 C2 1.383(3) . ? C1 C12A 1.390(3) . ? C1 H1 0.93 . ? C2 C3 1.393(3) . ? C2 H2 0.93 . ? C3 C4 1.384(3) . ? C3 H3 0.93 . ? C4 C4A 1.385(3) . ? C4 H4 0.93 . ? C4A C12A 1.385(2) . ? C4A C5 1.511(2) . ? C5 C13 1.523(3) . ? C5 C5A 1.568(2) . ? C5 H5 0.98 . ? C5A C6 1.500(3) . ? C5A C11A 1.558(2) . ? C5A H5A 0.98 . ? C6 C6A 1.476(3) . ? C6A C7 1.393(2) . ? C6A C10A 1.398(3) . ? C7 C8 1.378(3) . ? C7 H7 0.93 . ? C8 C9 1.384(3) . ? C8 H8 0.93 . ? C9 C10 1.378(2) . ? C9 H9 0.93 . ? C10 C10A 1.391(2) . ? C10 H10 0.93 . ? C10A C11 1.482(2) . ? C11 C11A 1.508(2) . ? C11A C12 1.569(3) . ? C11A H11A 0.98 . ? C12 C12A 1.509(3) . ? C12 C13 1.532(3) . ? C12 H12 0.98 . ? C13 C14 1.328(3) . ? C14 C15 1.498(3) . ? C14 C16 1.501(3) . ? C15 H15A 0.96 . ? C15 H15B 0.96 . ? C15 H15C 0.96 . ? C16 H16A 0.96 . ? C16 H16B 0.96 . ? C16 H16C 0.96 . ? O3 C22 1.219(2) . ? O4 C27 1.213(2) . ? C17 C28A 1.380(3) . ? C17 C18 1.391(3) . ? C17 H17 0.93 . ? C18 C19 1.384(3) . ? C18 H18 0.93 . ? C19 C20 1.389(3) . ? C19 H19 0.93 . ? C20 C20A 1.385(2) . ? C20 H20 0.93 . ? C20A C28A 1.395(3) . ? C20A C21 1.508(3) . ? C21 C29 1.522(3) . ? C21 C21A 1.577(3) . ? C21 H21 0.98 . ? C21A C22 1.510(3) . ? C21A C27A 1.555(3) . ? C21A H21A 0.98 . ? C22 C22A 1.485(3) . ? C22A C23 1.389(3) . ? C22A C26A 1.390(3) . ? C23 C24 1.379(3) . ? C23 H23 0.93 . ? C24 C25 1.378(3) . ? C24 H24 0.93 . ? C25 C26 1.378(3) . ? C25 H25 0.93 . ? C26 C26A 1.395(3) . ? C26 H26 0.93 . ? C26A C27 1.488(3) . ? C27 C27A 1.505(3) . ? C27A C28 1.579(3) . ? C27A H27A 0.98 . ? C28 C28A 1.510(3) . ? C28 C29 1.521(3) . ? C28 H30 0.98 . ? C29 C30 1.325(3) . ? C30 C31 1.502(3) . ? C30 C32 1.505(3) . ? C31 H31A 0.96 . ? C31 H31B 0.96 . ? C31 H31C 0.96 . ? C32 H32A 0.96 . ? C32 H32B 0.96 . ? C32 H32C 0.96 . ? O5 C38 1.223(2) . ? O6 C43 1.222(2) . ? C33 C44A 1.377(3) . ? C33 C34 1.389(3) . ? C33 H33 0.93 . ? C34 C35 1.381(3) . ? C34 H34 0.93 . ? C35 C36 1.393(3) . ? C35 H35 0.93 . ? C36 C36A 1.375(3) . ? C36 H36 0.93 . ? C36A C44A 1.395(3) . ? C36A C37 1.513(3) . ? C37 C45 1.520(3) . ? C37 C37A 1.580(3) . ? C37 H37 0.98 . ? C37A C38 1.501(3) . ? C37A C43A 1.556(3) . ? C37A H37A 0.98 . ? C38 C38A 1.481(3) . ? C38A C39 1.394(3) . ? C38A C42A 1.400(3) . ? C39 C40 1.382(3) . ? C39 H39 0.93 . ? C40 C41 1.386(3) . ? C40 H40 0.93 . ? C41 C42 1.375(3) . ? C41 H41 0.93 . ? C42 C42A 1.392(3) . ? C42 H42 0.93 . ? C42A C43 1.482(3) . ? C43 C43A 1.501(3) . ? C43A C44 1.575(3) . ? C43A H43A 0.98 . ? C44 C44A 1.507(3) . ? C44 C45 1.520(3) . ? C44 H44 0.98 . ? C45 C46 1.329(3) . ? C46 C48 1.500(3) . ? C46 C47 1.502(3) . ? C47 H47A 0.96 . ? C47 H47B 0.96 . ? C47 H47C 0.96 . ? C48 H48A 0.96 . ? C48 H48B 0.96 . ? C48 H48C 0.96 . ? 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 C1 C12A 117.81(19) . . ? C2 C1 H1 121.1 . . ? C12A C1 H1 121.1 . . ? C1 C2 C3 121.2(2) . . ? C1 C2 H2 119.4 . . ? C3 C2 H2 119.4 . . ? C4 C3 C2 120.7(2) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 C4A 118.25(19) . . ? C3 C4 H4 120.9 . . ? C4A C4 H4 120.9 . . ? C4 C4A C12A 120.93(19) . . ? C4 C4A C5 131.97(18) . . ? C12A C4A C5 107.10(17) . . ? C4A C5 C13 99.93(15) . . ? C4A C5 C5A 107.12(15) . . ? C13 C5 C5A 99.21(14) . . ? C4A C5 H5 116.1 . . ? C13 C5 H5 116.1 . . ? C5A C5 H5 116.1 . . ? C6 C5A C11A 116.86(16) . . ? C6 C5A C5 110.47(15) . . ? C11A C5A C5 103.01(14) . . ? C6 C5A H5A 108.7 . . ? C11A C5A H5A 108.7 . . ? C5 C5A H5A 108.7 . . ? O1 C6 C6A 120.24(18) . . ? O1 C6 C5A 119.48(18) . . ? C6A C6 C5A 120.27(17) . . ? C7 C6A C10A 119.65(17) . . ? C7 C6A C6 118.83(17) . . ? C10A C6A C6 121.52(17) . . ? C8 C7 C6A 120.01(18) . . ? C8 C7 H7 120 . . ? C6A C7 H7 120 . . ? C7 C8 C9 120.33(18) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C10 C9 C8 120.20(18) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C10A 120.23(18) . . ? C9 C10 H10 119.9 . . ? C10A C10 H10 119.9 . . ? C10 C10A C6A 119.49(17) . . ? C10 C10A C11 119.38(17) . . ? C6A C10A C11 121.09(17) . . ? O2 C11 C10A 120.46(17) . . ? O2 C11 C11A 119.25(17) . . ? C10A C11 C11A 120.20(16) . . ? C11 C11A C5A 117.67(15) . . ? C11 C11A C12 110.89(15) . . ? C5A C11A C12 103.06(14) . . ? C11 C11A H11A 108.3 . . ? C5A C11A H11A 108.3 . . ? C12 C11A H11A 108.3 . . ? C12A C12 C13 99.58(15) . . ? C12A C12 C11A 106.75(15) . . ? C13 C12 C11A 99.67(14) . . ? C12A C12 H12 116.1 . . ? C13 C12 H12 116.1 . . ? C11A C12 H12 116.1 . . ? C4A C12A C1 121.11(18) . . ? C4A C12A C12 106.80(16) . . ? C1 C12A C12 132.09(18) . . ? C14 C13 C5 131.58(18) . . ? C14 C13 C12 132.65(18) . . ? C5 C13 C12 95.76(15) . . ? C13 C14 C15 122.18(19) . . ? C13 C14 C16 122.45(19) . . ? C15 C14 C16 115.31(19) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C28A C17 C18 118.30(19) . . ? C28A C17 H17 120.8 . . ? C18 C17 H17 120.8 . . ? C19 C18 C17 120.81(19) . . ? C19 C18 H18 119.6 . . ? C17 C18 H18 119.6 . . ? C18 C19 C20 121.11(19) . . ? C18 C19 H19 119.4 . . ? C20 C19 H19 119.4 . . ? C20A C20 C19 118.00(19) . . ? C20A C20 H20 121 . . ? C19 C20 H20 121 . . ? C20 C20A C28A 120.96(18) . . ? C20 C20A C21 132.23(18) . . ? C28A C20A C21 106.81(16) . . ? C20A C21 C29 99.48(15) . . ? C20A C21 C21A 106.76(15) . . ? C29 C21 C21A 100.10(15) . . ? C20A C21 H21 116 . . ? C29 C21 H21 116 . . ? C21A C21 H21 116 . . ? C22 C21A C27A 116.93(16) . . ? C22 C21A C21 107.66(15) . . ? C27A C21A C21 102.94(14) . . ? C22 C21A H21A 109.7 . . ? C27A C21A H21A 109.7 . . ? C21 C21A H21A 109.7 . . ? O3 C22 C22A 121.26(18) . . ? O3 C22 C21A 119.65(18) . . ? C22A C22 C21A 118.96(18) . . ? C23 C22A C26A 119.86(19) . . ? C23 C22A C22 119.78(19) . . ? C26A C22A C22 120.32(18) . . ? C24 C23 C22A 120.0(2) . . ? C24 C23 H23 120 . . ? C22A C23 H23 120 . . ? C25 C24 C23 120.2(2) . . ? C25 C24 H24 119.9 . . ? C23 C24 H24 119.9 . . ? C26 C25 C24 120.4(2) . . ? C26 C25 H25 119.8 . . ? C24 C25 H25 119.8 . . ? C25 C26 C26A 119.8(2) . . ? C25 C26 H26 120.1 . . ? C26A C26 H26 120.1 . . ? C22A C26A C26 119.6(2) . . ? C22A C26A C27 120.63(18) . . ? C26 C26A C27 119.7(2) . . ? O4 C27 C26A 121.11(19) . . ? O4 C27 C27A 120.2(2) . . ? C26A C27 C27A 118.59(18) . . ? C27 C27A C21A 115.91(16) . . ? C27 C27A C28 109.69(15) . . ? C21A C27A C28 102.93(14) . . ? C27 C27A H27A 109.3 . . ? C21A C27A H27A 109.3 . . ? C28 C27A H27A 109.3 . . ? C28A C28 C29 99.46(15) . . ? C28A C28 C27A 106.30(15) . . ? C29 C28 C27A 100.48(15) . . ? C28A C28 H30 116.1 . . ? C29 C28 H30 116.1 . . ? C27A C28 H30 116.1 . . ? C17 C28A C20A 120.79(18) . . ? C17 C28A C28 132.66(18) . . ? C20A C28A C28 106.55(17) . . ? C30 C29 C28 131.81(18) . . ? C30 C29 C21 132.18(18) . . ? C28 C29 C21 96.00(16) . . ? C29 C30 C31 121.96(18) . . ? C29 C30 C32 122.79(18) . . ? C31 C30 C32 115.22(18) . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C30 C32 H32A 109.5 . . ? C30 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C30 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C44A C33 C34 118.38(19) . . ? C44A C33 H33 120.8 . . ? C34 C33 H33 120.8 . . ? C35 C34 C33 120.66(19) . . ? C35 C34 H34 119.7 . . ? C33 C34 H34 119.7 . . ? C34 C35 C36 121.06(19) . . ? C34 C35 H35 119.5 . . ? C36 C35 H35 119.5 . . ? C36A C36 C35 118.05(19) . . ? C36A C36 H36 121 . . ? C35 C36 H36 121 . . ? C36 C36A C44A 120.96(18) . . ? C36 C36A C37 132.56(18) . . ? C44A C36A C37 106.45(17) . . ? C36A C37 C45 99.52(15) . . ? C36A C37 C37A 107.09(15) . . ? C45 C37 C37A 99.59(14) . . ? C36A C37 H37 116.1 . . ? C45 C37 H37 116.1 . . ? C37A C37 H37 116.1 . . ? C38 C37A C43A 117.41(15) . . ? C38 C37A C37 107.75(15) . . ? C43A C37A C37 102.88(14) . . ? C38 C37A H37A 109.5 . . ? C43A C37A H37A 109.5 . . ? C37 C37A H37A 109.5 . . ? O5 C38 C38A 120.28(18) . . ? O5 C38 C37A 119.23(18) . . ? C38A C38 C37A 120.39(17) . . ? C39 C38A C42A 119.49(18) . . ? C39 C38A C38 119.28(17) . . ? C42A C38A C38 121.22(17) . . ? C40 C39 C38A 120.28(18) . . ? C40 C39 H39 119.9 . . ? C38A C39 H39 119.9 . . ? C39 C40 C41 119.92(18) . . ? C39 C40 H40 120 . . ? C41 C40 H40 120 . . ? C42 C41 C40 120.43(19) . . ? C42 C41 H41 119.8 . . ? C40 C41 H41 119.8 . . ? C41 C42 C42A 120.38(18) . . ? C41 C42 H42 119.8 . . ? C42A C42 H42 119.8 . . ? C42 C42A C38A 119.48(18) . . ? C42 C42A C43 119.33(17) . . ? C38A C42A C43 121.17(17) . . ? O6 C43 C42A 120.47(18) . . ? O6 C43 C43A 119.04(18) . . ? C42A C43 C43A 120.38(16) . . ? C43 C43A C37A 117.30(15) . . ? C43 C43A C44 107.46(15) . . ? C37A C43A C44 103.07(14) . . ? C43 C43A H43A 109.5 . . ? C37A C43A H43A 109.5 . . ? C44 C43A H43A 109.5 . . ? C44A C44 C45 99.36(15) . . ? C44A C44 C43A 107.24(15) . . ? C45 C44 C43A 99.73(14) . . ? C44A C44 H44 116 . . ? C45 C44 H44 116 . . ? C43A C44 H44 116 . . ? C33 C44A C36A 120.87(18) . . ? C33 C44A C44 132.08(19) . . ? C36A C44A C44 107.02(17) . . ? C46 C45 C44 131.43(18) . . ? C46 C45 C37 132.29(18) . . ? C44 C45 C37 96.28(16) . . ? C45 C46 C48 122.72(19) . . ? C45 C46 C47 121.81(19) . . ? C48 C46 C47 115.44(18) . . ? C46 C47 H47A 109.5 . . ? C46 C47 H47B 109.5 . . ? H47A C47 H47B 109.5 . . ? C46 C47 H47C 109.5 . . ? H47A C47 H47C 109.5 . . ? H47B C47 H47C 109.5 . . ? C46 C48 H48A 109.5 . . ? C46 C48 H48B 109.5 . . ? H48A C48 H48B 109.5 . . ? C46 C48 H48C 109.5 . . ? H48A C48 H48C 109.5 . . ? H48B C48 H48C 109.5 . . ? # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF data_i12160 _database_code_depnum_ccdc_archive 'CCDC 847353' #TrackingRef '7494_web_deposit_cif_file_0_Ching-TingChien_1317892119.CCDC-cif.txt' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C22 H18 O2' _chemical_formula_sum 'C22 H18 O2' _chemical_formula_weight 314.36 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.1278(4) _cell_length_b 9.4651(4) _cell_length_c 10.7576(5) _cell_angle_alpha 102.711(2) _cell_angle_beta 102.324(2) _cell_angle_gamma 91.986(2) _cell_volume 785.80(6) _cell_formula_units_Z 2 _cell_measurement_temperature 100.00(10) _cell_measurement_reflns_used 5395 _cell_measurement_theta_min 2.57 _cell_measurement_theta_max 26.42 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.329 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 332 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Bruker SADABS, 1996' _exptl_absorpt_correction_T_min 0.6749 _exptl_absorpt_correction_T_max 0.7454 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100.00(10) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_av_R_equivalents 0.0245 _diffrn_reflns_av_unetI/netI 0.0232 _diffrn_reflns_number 11193 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _reflns_number_total 3194 _reflns_number_gt 2780 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0448P)^2^+0.3123P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.005(2) _refine_ls_number_reflns 3194 _refine_ls_number_parameters 220 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0432 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.1003 _refine_ls_wR_factor_gt 0.096 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.331 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.04 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.28652(12) 0.59164(10) 0.44155(9) 0.0269(2) Uani 1 1 d . . . O2 O 0.48916(14) 1.08945(10) 0.80994(10) 0.0310(3) Uani 1 1 d . . . C1 C 0.18718(16) 0.84623(13) 0.90421(12) 0.0192(3) Uani 1 1 d . . . H1 H 0.2173 0.9332 0.967 0.023 Uiso 1 1 calc R . . C2 C 0.02009(16) 0.78668(14) 0.86355(13) 0.0218(3) Uani 1 1 d . . . H2 H -0.0621 0.8334 0.9014 0.026 Uiso 1 1 calc R . . C3 C -0.02574(16) 0.65876(15) 0.76747(13) 0.0217(3) Uani 1 1 d . . . H3 H -0.1382 0.6212 0.7417 0.026 Uiso 1 1 calc R . . C4 C 0.09435(16) 0.58573(14) 0.70910(12) 0.0194(3) Uani 1 1 d . . . H4 H 0.0632 0.5013 0.6432 0.023 Uiso 1 1 calc R . . C4A C 0.26131(15) 0.64245(13) 0.75210(12) 0.0171(3) Uani 1 1 d . . . C5 C 0.42317(15) 0.59007(13) 0.71633(12) 0.0172(3) Uani 1 1 d . . . H5 H 0.4204 0.4864 0.6755 0.021 Uiso 1 1 calc R . . C5A C 0.48097(15) 0.69928(13) 0.63994(12) 0.0172(3) Uani 1 1 d . . . H5A H 0.5816 0.6651 0.6103 0.021 Uiso 1 1 calc R . . C6 C 0.34586(16) 0.70423(14) 0.52102(12) 0.0187(3) Uani 1 1 d . . . C6A C 0.28687(16) 0.84683(14) 0.50087(12) 0.0195(3) Uani 1 1 d . . . C7 C 0.17428(17) 0.84992(16) 0.38349(13) 0.0247(3) Uani 1 1 d . . . H7 H 0.1379 0.7643 0.32 0.03 Uiso 1 1 calc R . . C8 C 0.11708(18) 0.98016(17) 0.36183(14) 0.0293(3) Uani 1 1 d . . . H8 H 0.043 0.9819 0.2834 0.035 Uiso 1 1 calc R . . C9 C 0.16973(18) 1.10845(16) 0.45665(15) 0.0291(3) Uani 1 1 d . . . H9 H 0.1307 1.1957 0.4415 0.035 Uiso 1 1 calc R . . C10 C 0.27994(18) 1.10664(15) 0.57323(14) 0.0252(3) Uani 1 1 d . . . H10 H 0.3144 1.1927 0.6366 0.03 Uiso 1 1 calc R . . C10A C 0.33985(16) 0.97595(14) 0.59635(12) 0.0198(3) Uani 1 1 d . . . C11 C 0.45650(16) 0.97851(13) 0.72407(12) 0.0198(3) Uani 1 1 d . . . C11A C 0.53550(15) 0.84208(13) 0.74759(12) 0.0174(3) Uani 1 1 d . . . H11A H 0.6583 0.861 0.7623 0.021 Uiso 1 1 calc R . . C12 C 0.49689(15) 0.80086(13) 0.87293(12) 0.0167(3) Uani 1 1 d . . . H12 H 0.5527 0.8652 0.9571 0.02 Uiso 1 1 calc R . . C12A C 0.30702(15) 0.77209(13) 0.84830(12) 0.0164(3) Uani 1 1 d . . . C13 C 0.54531(15) 0.64480(13) 0.84930(12) 0.0170(3) Uani 1 1 d . . . C14 C 0.65460(16) 0.57842(14) 0.92279(12) 0.0193(3) Uani 1 1 d . . . C15 C 0.68376(18) 0.42116(14) 0.88068(14) 0.0248(3) Uani 1 1 d . . . H15A H 0.6187 0.382 0.7933 0.037 Uiso 1 1 calc R . . H15B H 0.6497 0.3684 0.939 0.037 Uiso 1 1 calc R . . H15C H 0.8016 0.4125 0.8828 0.037 Uiso 1 1 calc R . . C16 C 0.75760(17) 0.65496(15) 1.05578(13) 0.0248(3) Uani 1 1 d . . . H16A H 0.7328 0.7548 1.0748 0.037 Uiso 1 1 calc R . . H16B H 0.8757 0.6502 1.0568 0.037 Uiso 1 1 calc R . . H16C H 0.73 0.6087 1.1206 0.037 Uiso 1 1 calc R . . 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 0.0318(6) 0.0244(5) 0.0205(5) 0.0020(4) 0.0005(4) 0.0034(4) O2 0.0454(6) 0.0186(5) 0.0261(5) 0.0045(4) 0.0032(5) 0.0015(4) C1 0.0214(6) 0.0192(6) 0.0185(6) 0.0071(5) 0.0045(5) 0.0049(5) C2 0.0191(6) 0.0277(7) 0.0239(7) 0.0126(5) 0.0086(5) 0.0091(5) C3 0.0131(6) 0.0300(7) 0.0247(7) 0.0146(6) 0.0020(5) 0.0008(5) C4 0.0194(6) 0.0203(6) 0.0185(6) 0.0078(5) 0.0013(5) -0.0004(5) C4A 0.0180(6) 0.0188(6) 0.0173(6) 0.0094(5) 0.0043(5) 0.0035(5) C5 0.0174(6) 0.0157(6) 0.0194(6) 0.0059(5) 0.0039(5) 0.0028(5) C5A 0.0161(6) 0.0181(6) 0.0190(6) 0.0060(5) 0.0057(5) 0.0045(5) C6 0.0191(6) 0.0219(6) 0.0171(6) 0.0055(5) 0.0076(5) 0.0031(5) C6A 0.0183(6) 0.0248(7) 0.0199(6) 0.0103(5) 0.0082(5) 0.0052(5) C7 0.0219(7) 0.0335(7) 0.0217(7) 0.0109(6) 0.0060(5) 0.0053(6) C8 0.0239(7) 0.0436(9) 0.0275(7) 0.0217(6) 0.0060(6) 0.0100(6) C9 0.0280(8) 0.0323(8) 0.0385(8) 0.0237(7) 0.0149(6) 0.0135(6) C10 0.0287(7) 0.0233(7) 0.0303(7) 0.0131(6) 0.0133(6) 0.0069(5) C10A 0.0191(6) 0.0225(6) 0.0231(6) 0.0110(5) 0.0100(5) 0.0048(5) C11 0.0220(7) 0.0176(6) 0.0221(6) 0.0068(5) 0.0084(5) 0.0000(5) C11A 0.0140(6) 0.0194(6) 0.0195(6) 0.0068(5) 0.0031(5) 0.0012(5) C12 0.0160(6) 0.0176(6) 0.0169(6) 0.0051(5) 0.0030(5) 0.0019(5) C12A 0.0171(6) 0.0187(6) 0.0162(6) 0.0103(5) 0.0031(5) 0.0031(5) C13 0.0146(6) 0.0197(6) 0.0189(6) 0.0066(5) 0.0061(5) 0.0019(5) C14 0.0164(6) 0.0241(6) 0.0213(6) 0.0105(5) 0.0072(5) 0.0034(5) C15 0.0257(7) 0.0267(7) 0.0278(7) 0.0140(6) 0.0094(6) 0.0101(5) C16 0.0201(7) 0.0328(7) 0.0241(7) 0.0134(6) 0.0027(5) 0.0061(6) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C6 1.2193(16) . ? O2 C11 1.2147(16) . ? C1 C12A 1.3837(17) . ? C1 C2 1.3922(18) . ? C1 H1 0.93 . ? C2 C3 1.3881(19) . ? C2 H2 0.93 . ? C3 C4 1.3936(18) . ? C3 H3 0.93 . ? C4 C4A 1.3842(18) . ? C4 H4 0.93 . ? C4A C12A 1.4000(17) . ? C4A C5 1.5172(17) . ? C5 C13 1.5271(17) . ? C5 C5A 1.5714(17) . ? C5 H5 0.98 . ? C5A C6 1.5083(17) . ? C5A C11A 1.5540(16) . ? C5A H5A 0.98 . ? C6 C6A 1.4926(17) . ? C6A C10A 1.3987(18) . ? C6A C7 1.3991(18) . ? C7 C8 1.382(2) . ? C7 H7 0.93 . ? C8 C9 1.389(2) . ? C8 H8 0.93 . ? C9 C10 1.381(2) . ? C9 H9 0.93 . ? C10 C10A 1.3980(18) . ? C10 H10 0.93 . ? C10A C11 1.4883(18) . ? C11 C11A 1.5085(17) . ? C11A C12 1.5725(17) . ? C11A H11A 0.98 . ? C12 C12A 1.5135(17) . ? C12 C13 1.5228(17) . ? C12 H12 0.98 . ? C13 C14 1.3290(18) . ? C14 C15 1.5002(18) . ? C14 C16 1.5043(18) . ? C15 H15A 0.96 . ? C15 H15B 0.96 . ? C15 H15C 0.96 . ? C16 H16A 0.96 . ? C16 H16B 0.96 . ? C16 H16C 0.96 . ? 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 C12A C1 C2 117.97(12) . . ? C12A C1 H1 121 . . ? C2 C1 H1 121 . . ? C3 C2 C1 121.06(12) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C2 C3 C4 120.96(12) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C4A C4 C3 118.06(12) . . ? C4A C4 H4 121 . . ? C3 C4 H4 121 . . ? C4 C4A C12A 120.84(11) . . ? C4 C4A C5 132.45(11) . . ? C12A C4A C5 106.70(10) . . ? C4A C5 C13 99.24(9) . . ? C4A C5 C5A 105.82(9) . . ? C13 C5 C5A 100.05(9) . . ? C4A C5 H5 116.4 . . ? C13 C5 H5 116.4 . . ? C5A C5 H5 116.4 . . ? C6 C5A C11A 117.80(10) . . ? C6 C5A C5 111.21(10) . . ? C11A C5A C5 103.22(9) . . ? C6 C5A H5A 108.1 . . ? C11A C5A H5A 108.1 . . ? C5 C5A H5A 108.1 . . ? O1 C6 C6A 120.50(12) . . ? O1 C6 C5A 119.67(11) . . ? C6A C6 C5A 119.83(11) . . ? C10A C6A C7 119.63(12) . . ? C10A C6A C6 121.76(11) . . ? C7 C6A C6 118.61(12) . . ? C8 C7 C6A 120.05(13) . . ? C8 C7 H7 120 . . ? C6A C7 H7 120 . . ? C7 C8 C9 120.33(13) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C10 C9 C8 120.15(13) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C10A 120.24(13) . . ? C9 C10 H10 119.9 . . ? C10A C10 H10 119.9 . . ? C10 C10A C6A 119.60(12) . . ? C10 C10A C11 118.51(12) . . ? C6A C10A C11 121.88(11) . . ? O2 C11 C10A 120.75(12) . . ? O2 C11 C11A 119.43(12) . . ? C10A C11 C11A 119.82(11) . . ? C11 C11A C5A 118.18(10) . . ? C11 C11A C12 111.65(10) . . ? C5A C11A C12 103.34(9) . . ? C11 C11A H11A 107.7 . . ? C5A C11A H11A 107.7 . . ? C12 C11A H11A 107.7 . . ? C12A C12 C13 99.38(9) . . ? C12A C12 C11A 106.95(9) . . ? C13 C12 C11A 99.27(9) . . ? C12A C12 H12 116.2 . . ? C13 C12 H12 116.2 . . ? C11A C12 H12 116.2 . . ? C1 C12A C4A 121.06(11) . . ? C1 C12A C12 131.99(11) . . ? C4A C12A C12 106.93(10) . . ? C14 C13 C12 131.24(12) . . ? C14 C13 C5 132.15(12) . . ? C12 C13 C5 96.59(9) . . ? C13 C14 C15 122.82(12) . . ? C13 C14 C16 122.52(12) . . ? C15 C14 C16 114.66(11) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF data_i12161 _database_code_depnum_ccdc_archive 'CCDC 847354' #TrackingRef '7494_web_deposit_cif_file_0_Ching-TingChien_1317892119.CCDC-cif.txt' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C22 H18' _chemical_formula_sum 'C22 H18' _chemical_formula_weight 282.36 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 14.9138(13) _cell_length_b 15.2530(12) _cell_length_c 15.1360(14) _cell_angle_alpha 90 _cell_angle_beta 118.815(4) _cell_angle_gamma 90 _cell_volume 3016.8(5) _cell_formula_units_Z 8 _cell_measurement_temperature 100.00(10) _cell_measurement_reflns_used 3203 _cell_measurement_theta_min 2.98 _cell_measurement_theta_max 26.58 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.243 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.07 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Bruker SADABS, 1996' _exptl_absorpt_correction_T_min 0.6749 _exptl_absorpt_correction_T_max 0.7454 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100.00(10) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_av_R_equivalents 0.0462 _diffrn_reflns_av_unetI/netI 0.0549 _diffrn_reflns_number 12003 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 3090 _reflns_number_gt 2267 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0683P)^2^+4.5341P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 3090 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0839 _refine_ls_R_factor_gt 0.0609 _refine_ls_wR_factor_ref 0.1648 _refine_ls_wR_factor_gt 0.1515 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.641 _refine_diff_density_min -0.399 _refine_diff_density_rms 0.058 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.38361(17) -0.16075(14) 0.27442(18) 0.0247(5) Uani 1 1 d . . . H1 H 0.4297 -0.2003 0.2717 0.03 Uiso 1 1 calc R . . C2 C 0.36333(18) -0.16181(15) 0.35383(18) 0.0272(6) Uani 1 1 d . . . H2 H 0.3954 -0.2029 0.4051 0.033 Uiso 1 1 calc R . . C3 C 0.29424(19) -0.10116(16) 0.35833(18) 0.0291(6) Uani 1 1 d . . . H3 H 0.2813 -0.1026 0.4126 0.035 Uiso 1 1 calc R . . C4 C 0.24561(18) -0.03980(15) 0.28304(18) 0.0264(5) Uani 1 1 d . . . H4 H 0.2003 0.0005 0.2859 0.032 Uiso 1 1 calc R . . C4A C 0.26645(17) -0.03989(14) 0.20220(17) 0.0237(5) Uani 1 1 d . . . C5 C 0.22388(16) 0.01630(14) 0.10770(17) 0.0211(5) Uani 1 1 d . . . H5 H 0.1595 0.0474 0.0884 0.025 Uiso 1 1 calc R . . C5A C 0.31315(16) 0.07000(14) 0.11346(16) 0.0181(5) Uani 1 1 d . . . C6 C 0.33036(16) 0.15780(14) 0.11711(16) 0.0191(5) Uani 1 1 d . . . H6 H 0.284 0.1972 0.1195 0.023 Uiso 1 1 calc R . . C6A C 0.42070(16) 0.18854(14) 0.11721(16) 0.0195(5) Uani 1 1 d . . . C7 C 0.44253(18) 0.27923(14) 0.11908(18) 0.0245(5) Uani 1 1 d . . . H7 H 0.3967 0.3202 0.1197 0.029 Uiso 1 1 calc R . . C8 C 0.53014(18) 0.30731(15) 0.11997(19) 0.0282(6) Uani 1 1 d . . . H8 H 0.5435 0.3671 0.122 0.034 Uiso 1 1 calc R . . C9 C 0.60010(17) 0.24694(15) 0.11785(18) 0.0257(5) Uani 1 1 d . . . H9 H 0.6595 0.2667 0.1186 0.031 Uiso 1 1 calc R . . C10 C 0.58079(16) 0.15873(14) 0.11467(17) 0.0216(5) Uani 1 1 d . . . H10 H 0.6271 0.1191 0.1126 0.026 Uiso 1 1 calc R . . C10A C 0.49135(15) 0.12703(13) 0.11447(15) 0.0176(5) Uani 1 1 d . . . C11 C 0.47034(16) 0.03552(13) 0.11017(15) 0.0170(5) Uani 1 1 d . . . H11 H 0.5156 -0.0052 0.1078 0.02 Uiso 1 1 calc R . . C11A C 0.38304(16) 0.00878(13) 0.10950(15) 0.0163(5) Uani 1 1 d . . . C12 C 0.33613(16) -0.08213(14) 0.10060(17) 0.0191(5) Uani 1 1 d . . . H12 H 0.3624 -0.1295 0.0756 0.023 Uiso 1 1 calc R . . C12A C 0.33361(17) -0.09915(15) 0.19780(17) 0.0232(5) Uani 1 1 d . . . C13 C 0.22259(17) -0.05729(15) 0.03498(17) 0.0234(5) Uani 1 1 d . . . C14 C 0.14757(18) -0.08882(15) -0.04995(18) 0.0255(5) Uani 1 1 d . . . C15 C 0.04058(18) -0.05465(17) -0.0984(2) 0.0323(6) Uani 1 1 d . . . H15A H 0.0364 -0.0071 -0.059 0.048 Uiso 1 1 calc R . . H15B H -0.0051 -0.1007 -0.1022 0.048 Uiso 1 1 calc R . . H15C H 0.0216 -0.0342 -0.1651 0.048 Uiso 1 1 calc R . . C16 C 0.1629(2) -0.16398(16) -0.10464(19) 0.0302(6) Uani 1 1 d . . . H16A H 0.2332 -0.1822 -0.0695 0.045 Uiso 1 1 calc R . . H16B H 0.1456 -0.1461 -0.1718 0.045 Uiso 1 1 calc R . . H16C H 0.1197 -0.2119 -0.1077 0.045 Uiso 1 1 calc R . . 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 0.0241(12) 0.0225(11) 0.0239(13) -0.0046(9) 0.0086(10) -0.0054(9) C2 0.0274(13) 0.0237(12) 0.0238(13) 0.0019(10) 0.0069(11) -0.0076(10) C3 0.0344(14) 0.0352(13) 0.0222(13) -0.0083(10) 0.0172(11) -0.0165(11) C4 0.0229(12) 0.0297(12) 0.0276(13) -0.0093(10) 0.0129(11) -0.0063(10) C4A 0.0241(12) 0.0229(11) 0.0200(12) -0.0044(9) 0.0073(10) -0.0085(9) C5 0.0181(11) 0.0206(11) 0.0269(13) 0.0009(9) 0.0127(10) 0.0019(9) C5A 0.0163(11) 0.0224(11) 0.0153(11) 0.0007(9) 0.0074(9) 0.0023(8) C6 0.0193(11) 0.0198(11) 0.0160(11) -0.0017(8) 0.0068(9) 0.0041(9) C6A 0.0206(11) 0.0199(11) 0.0149(11) -0.0010(8) 0.0061(9) 0.0007(9) C7 0.0257(12) 0.0182(11) 0.0274(13) 0.0003(9) 0.0111(11) 0.0008(9) C8 0.0299(13) 0.0186(11) 0.0325(14) 0.0007(10) 0.0123(11) -0.0039(10) C9 0.0208(12) 0.0247(12) 0.0304(14) 0.0019(10) 0.0114(11) -0.0038(9) C10 0.0183(11) 0.0233(11) 0.0218(12) 0.0037(9) 0.0085(10) 0.0023(9) C10A 0.0179(11) 0.0203(11) 0.0127(11) 0.0031(8) 0.0059(9) 0.0005(9) C11 0.0169(11) 0.0189(10) 0.0144(11) 0.0032(8) 0.0069(9) 0.0055(8) C11A 0.0191(11) 0.0159(10) 0.0121(10) 0.0020(8) 0.0060(9) 0.0010(8) C12 0.0198(11) 0.0168(10) 0.0232(12) 0.0006(9) 0.0124(10) 0.0009(9) C12A 0.0230(12) 0.0271(12) 0.0177(12) -0.0030(9) 0.0084(10) -0.0084(9) C13 0.0263(12) 0.0276(12) 0.0151(11) 0.0035(9) 0.0089(10) -0.0074(10) C14 0.0287(13) 0.0261(12) 0.0235(13) 0.0015(10) 0.0141(11) 0.0000(10) C15 0.0244(13) 0.0368(14) 0.0305(14) 0.0012(11) 0.0091(11) 0.0032(11) C16 0.0384(15) 0.0282(12) 0.0271(14) -0.0019(10) 0.0182(12) -0.0040(11) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C2 1.374(3) . ? C1 C12A 1.396(3) . ? C1 H1 0.93 . ? C2 C3 1.411(3) . ? C2 H2 0.93 . ? C3 C4 1.380(3) . ? C3 H3 0.93 . ? C4 C4A 1.400(3) . ? C4 H4 0.93 . ? C4A C12A 1.374(3) . ? C4A C5 1.519(3) . ? C5 C5A 1.529(3) . ? C5 C13 1.566(3) . ? C5 H5 0.98 . ? C5A C6 1.360(3) . ? C5A C11A 1.422(3) . ? C6 C6A 1.426(3) . ? C6 H6 0.93 . ? C6A C7 1.418(3) . ? C6A C10A 1.426(3) . ? C7 C8 1.369(3) . ? C7 H7 0.93 . ? C8 C9 1.403(3) . ? C8 H8 0.93 . ? C9 C10 1.372(3) . ? C9 H9 0.93 . ? C10 C10A 1.417(3) . ? C10 H10 0.93 . ? C10A C11 1.425(3) . ? C11 C11A 1.360(3) . ? C11 H11 0.93 . ? C11A C12 1.529(3) . ? C12 C12A 1.512(3) . ? C12 C13 1.541(3) . ? C12 H12 0.98 . ? C13 C14 1.323(3) . ? C14 C15 1.492(3) . ? C14 C16 1.495(3) . ? C15 H15A 0.96 . ? C15 H15B 0.96 . ? C15 H15C 0.96 . ? C16 H16A 0.96 . ? C16 H16B 0.96 . ? C16 H16C 0.96 . ? 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 C1 C12A 118.7(2) . . ? C2 C1 H1 120.7 . . ? C12A C1 H1 120.7 . . ? C1 C2 C3 120.6(2) . . ? C1 C2 H2 119.7 . . ? C3 C2 H2 119.7 . . ? C4 C3 C2 120.7(2) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C3 C4 C4A 118.1(2) . . ? C3 C4 H4 120.9 . . ? C4A C4 H4 120.9 . . ? C12A C4A C4 121.1(2) . . ? C12A C4A C5 108.00(19) . . ? C4 C4A C5 130.9(2) . . ? C4A C5 C5A 106.93(18) . . ? C4A C5 C13 96.63(16) . . ? C5A C5 C13 98.02(16) . . ? C4A C5 H5 117.3 . . ? C5A C5 H5 117.3 . . ? C13 C5 H5 117.3 . . ? C6 C5A C11A 121.37(19) . . ? C6 C5A C5 132.22(19) . . ? C11A C5A C5 106.35(17) . . ? C5A C6 C6A 118.93(19) . . ? C5A C6 H6 120.5 . . ? C6A C6 H6 120.5 . . ? C7 C6A C6 121.9(2) . . ? C7 C6A C10A 118.4(2) . . ? C6 C6A C10A 119.64(19) . . ? C8 C7 C6A 120.9(2) . . ? C8 C7 H7 119.5 . . ? C6A C7 H7 119.5 . . ? C7 C8 C9 120.7(2) . . ? C7 C8 H8 119.6 . . ? C9 C8 H8 119.6 . . ? C10 C9 C8 119.9(2) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C9 C10 C10A 121.1(2) . . ? C9 C10 H10 119.5 . . ? C10A C10 H10 119.5 . . ? C10 C10A C11 121.34(19) . . ? C10 C10A C6A 118.90(19) . . ? C11 C10A C6A 119.75(18) . . ? C11A C11 C10A 118.87(19) . . ? C11A C11 H11 120.6 . . ? C10A C11 H11 120.6 . . ? C11 C11A C5A 121.42(19) . . ? C11 C11A C12 131.94(19) . . ? C5A C11A C12 106.59(17) . . ? C12A C12 C11A 107.15(17) . . ? C12A C12 C13 97.72(16) . . ? C11A C12 C13 98.50(16) . . ? C12A C12 H12 116.8 . . ? C11A C12 H12 116.8 . . ? C13 C12 H12 116.8 . . ? C4A C12A C1 120.8(2) . . ? C4A C12A C12 107.13(19) . . ? C1 C12A C12 132.1(2) . . ? C14 C13 C12 133.5(2) . . ? C14 C13 C5 131.5(2) . . ? C12 C13 C5 94.92(17) . . ? C13 C14 C15 123.6(2) . . ? C13 C14 C16 122.3(2) . . ? C15 C14 C16 114.1(2) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? 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 C12A C1 C2 C3 -0.7(3) . . . . ? C1 C2 C3 C4 0.1(3) . . . . ? C2 C3 C4 C4A 0.3(3) . . . . ? C3 C4 C4A C12A -0.2(3) . . . . ? C3 C4 C4A C5 178.0(2) . . . . ? C12A C4A C5 C5A -66.0(2) . . . . ? C4 C4A C5 C5A 115.6(2) . . . . ? C12A C4A C5 C13 34.5(2) . . . . ? C4 C4A C5 C13 -143.9(2) . . . . ? C4A C5 C5A C6 -118.4(3) . . . . ? C13 C5 C5A C6 142.1(2) . . . . ? C4A C5 C5A C11A 64.5(2) . . . . ? C13 C5 C5A C11A -35.0(2) . . . . ? C11A C5A C6 C6A -0.2(3) . . . . ? C5 C5A C6 C6A -176.9(2) . . . . ? C5A C6 C6A C7 178.8(2) . . . . ? C5A C6 C6A C10A -0.6(3) . . . . ? C6 C6A C7 C8 179.5(2) . . . . ? C10A C6A C7 C8 -1.1(3) . . . . ? C6A C7 C8 C9 0.8(4) . . . . ? C7 C8 C9 C10 0.1(4) . . . . ? C8 C9 C10 C10A -0.6(3) . . . . ? C9 C10 C10A C11 179.4(2) . . . . ? C9 C10 C10A C6A 0.3(3) . . . . ? C7 C6A C10A C10 0.6(3) . . . . ? C6 C6A C10A C10 -180.0(2) . . . . ? C7 C6A C10A C11 -178.5(2) . . . . ? C6 C6A C10A C11 0.9(3) . . . . ? C10 C10A C11 C11A -179.57(19) . . . . ? C6A C10A C11 C11A -0.5(3) . . . . ? C10A C11 C11A C5A -0.3(3) . . . . ? C10A C11 C11A C12 176.8(2) . . . . ? C6 C5A C11A C11 0.6(3) . . . . ? C5 C5A C11A C11 178.12(19) . . . . ? C6 C5A C11A C12 -177.1(2) . . . . ? C5 C5A C11A C12 0.4(2) . . . . ? C11 C11A C12 C12A 116.8(2) . . . . ? C5A C11A C12 C12A -65.8(2) . . . . ? C11 C11A C12 C13 -142.4(2) . . . . ? C5A C11A C12 C13 35.0(2) . . . . ? C4 C4A C12A C1 -0.4(3) . . . . ? C5 C4A C12A C1 -178.97(19) . . . . ? C4 C4A C12A C12 178.80(19) . . . . ? C5 C4A C12A C12 0.3(2) . . . . ? C2 C1 C12A C4A 0.9(3) . . . . ? C2 C1 C12A C12 -178.1(2) . . . . ? C11A C12 C12A C4A 65.8(2) . . . . ? C13 C12 C12A C4A -35.6(2) . . . . ? C11A C12 C12A C1 -115.1(3) . . . . ? C13 C12 C12A C1 143.5(2) . . . . ? C12A C12 C13 C14 -122.4(3) . . . . ? C11A C12 C13 C14 128.9(3) . . . . ? C12A C12 C13 C5 54.40(17) . . . . ? C11A C12 C13 C5 -54.33(17) . . . . ? C4A C5 C13 C14 123.2(3) . . . . ? C5A C5 C13 C14 -128.6(3) . . . . ? C4A C5 C13 C12 -53.70(17) . . . . ? C5A C5 C13 C12 54.51(17) . . . . ? C12 C13 C14 C15 177.9(2) . . . . ? C5 C13 C14 C15 2.2(4) . . . . ? C12 C13 C14 C16 -0.6(4) . . . . ? C5 C13 C14 C16 -176.3(2) . . . . ? # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF data_ic14839 _database_code_depnum_ccdc_archive 'CCDC 847355' #TrackingRef '7494_web_deposit_cif_file_0_Ching-TingChien_1317892119.CCDC-cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H12 O' _chemical_formula_weight 256.29 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.8708(2) _cell_length_b 7.6845(3) _cell_length_c 28.2976(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1276.62(8) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 6845 _cell_measurement_theta_min 1.44 _cell_measurement_theta_max 27.50 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.333 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9761 _exptl_absorpt_correction_T_max 0.9944 _exptl_absorpt_process_details ? _chemical_absolute_configuration ad _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'NONIUS KappaCCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6845 _diffrn_reflns_av_R_equivalents 0.0439 _diffrn_reflns_av_sigmaI/netI 0.0543 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 1.44 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2886 _reflns_number_gt 2061 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0560P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(2) _refine_ls_number_reflns 2886 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0684 _refine_ls_R_factor_gt 0.0389 _refine_ls_wR_factor_ref 0.1080 _refine_ls_wR_factor_gt 0.0824 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.0891(3) -0.09640(19) 0.07809(5) 0.0617(4) Uani 1 1 d . . . C1 C 0.0862(4) 0.4678(3) 0.06767(6) 0.0465(5) Uani 1 1 d . . . H1 H -0.0486 0.5330 0.0733 0.056 Uiso 1 1 calc R . . C2 C 0.2600(4) 0.5346(3) 0.03987(6) 0.0530(5) Uani 1 1 d . . . H2 H 0.2457 0.6484 0.0271 0.064 Uiso 1 1 calc R . . C3 C 0.4538(4) 0.4384(3) 0.03050(6) 0.0529(6) Uani 1 1 d . . . H3 H 0.5704 0.4870 0.0113 0.064 Uiso 1 1 calc R . . C4 C 0.4806(3) 0.2720(3) 0.04867(6) 0.0494(5) Uani 1 1 d . . . H4 H 0.6117 0.2046 0.0414 0.059 Uiso 1 1 calc R . . C5 C 0.2879(3) 0.0333(3) 0.10241(6) 0.0461(5) Uani 1 1 d . . . H5 H 0.3858 -0.0646 0.0910 0.055 Uiso 1 1 calc R . . C6 C 0.4213(3) 0.0181(2) 0.19127(6) 0.0407(4) Uani 1 1 d . . . H6 H 0.5579 -0.0436 0.1846 0.049 Uiso 1 1 calc R . . C7 C 0.5039(3) 0.0148(2) 0.27708(6) 0.0427(5) Uani 1 1 d . . . H7 H 0.6442 -0.0428 0.2712 0.051 Uiso 1 1 calc R . . C8 C 0.4436(4) 0.0527(3) 0.32243(7) 0.0469(5) Uani 1 1 d . . . H8 H 0.5413 0.0211 0.3478 0.056 Uiso 1 1 calc R . . C9 C 0.2370(4) 0.1385(2) 0.33178(7) 0.0471(5) Uani 1 1 d . . . H9 H 0.1958 0.1647 0.3634 0.056 Uiso 1 1 calc R . . C10 C 0.0951(3) 0.1843(2) 0.29554(6) 0.0419(5) Uani 1 1 d . . . H10 H -0.0441 0.2420 0.3024 0.050 Uiso 1 1 calc R . . C11 C 0.0101(3) 0.1987(2) 0.20983(6) 0.0383(4) Uani 1 1 d . . . H11 H -0.1290 0.2582 0.2156 0.046 Uiso 1 1 calc R . . C12 C -0.0409(3) 0.1933(3) 0.11789(6) 0.0423(5) Uani 1 1 d . . . H12 H -0.2063 0.2244 0.1186 0.051 Uiso 1 1 calc R . . C13 C 0.0248(3) 0.0157(3) 0.09544(6) 0.0469(5) Uani 1 1 d . . . C1A C 0.1139(3) 0.3037(3) 0.08708(6) 0.0396(4) Uani 1 1 d . . . C4A C 0.3110(3) 0.2069(3) 0.07759(6) 0.0418(5) Uani 1 1 d . . . C5A C 0.2806(3) 0.0676(2) 0.15556(6) 0.0399(5) Uani 1 1 d . . . C6A C 0.3617(3) 0.0596(2) 0.23862(6) 0.0368(4) Uani 1 1 d . . . C10A C 0.1518(3) 0.1474(2) 0.24805(6) 0.0359(4) Uani 1 1 d . . . C11A C 0.0758(3) 0.1617(2) 0.16472(6) 0.0369(4) 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 0.0808(10) 0.0499(9) 0.0543(8) 0.0008(7) -0.0138(9) -0.0131(9) C1 0.0553(11) 0.0449(12) 0.0392(10) -0.0025(9) -0.0030(10) 0.0059(11) C2 0.0723(14) 0.0450(13) 0.0417(10) 0.0024(9) -0.0032(11) -0.0051(12) C3 0.0548(13) 0.0677(16) 0.0364(10) 0.0017(11) 0.0000(10) -0.0095(12) C4 0.0432(11) 0.0690(15) 0.0358(9) -0.0067(10) -0.0010(9) 0.0047(11) C5 0.0506(11) 0.0447(12) 0.0431(10) -0.0068(10) 0.0001(9) 0.0119(10) C6 0.0380(9) 0.0345(10) 0.0496(11) -0.0003(8) 0.0003(9) 0.0058(9) C7 0.0424(10) 0.0323(10) 0.0535(12) 0.0032(8) -0.0048(9) 0.0013(9) C8 0.0554(12) 0.0378(11) 0.0473(11) 0.0063(9) -0.0095(10) -0.0061(10) C9 0.0588(13) 0.0406(12) 0.0417(10) 0.0026(9) 0.0027(10) -0.0074(10) C10 0.0433(11) 0.0361(10) 0.0462(10) 0.0018(9) 0.0059(9) -0.0023(9) C11 0.0334(10) 0.0317(10) 0.0498(10) 0.0007(8) 0.0028(8) 0.0024(8) C12 0.0357(10) 0.0465(11) 0.0447(10) -0.0006(9) -0.0019(9) 0.0046(9) C13 0.0583(12) 0.0450(12) 0.0374(10) 0.0030(9) -0.0070(10) -0.0046(11) C1A 0.0424(10) 0.0418(11) 0.0345(9) -0.0047(8) -0.0029(8) 0.0037(9) C4A 0.0444(11) 0.0458(12) 0.0351(9) -0.0055(9) -0.0025(9) 0.0047(9) C5A 0.0418(10) 0.0348(11) 0.0430(10) -0.0019(9) 0.0009(9) 0.0043(9) C6A 0.0376(10) 0.0285(10) 0.0443(10) 0.0026(8) -0.0006(8) -0.0015(8) C10A 0.0350(10) 0.0293(10) 0.0433(10) 0.0016(8) 0.0020(8) -0.0030(8) C11A 0.0345(9) 0.0340(10) 0.0423(10) 0.0011(8) 0.0008(8) 0.0022(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C13 1.196(2) . ? C1 C1A 1.385(3) . ? C1 C2 1.387(3) . ? C2 C3 1.383(3) . ? C3 C4 1.387(3) . ? C4 C4A 1.382(3) . ? C5 C4A 1.514(3) . ? C5 C5A 1.528(2) . ? C5 C13 1.563(3) . ? C6 C5A 1.359(2) . ? C6 C6A 1.421(3) . ? C7 C8 1.363(2) . ? C7 C6A 1.414(2) . ? C8 C9 1.405(3) . ? C9 C10 1.368(3) . ? C10 C10A 1.413(2) . ? C11 C11A 1.364(2) . ? C11 C10A 1.420(2) . ? C12 C11A 1.511(2) . ? C12 C1A 1.519(3) . ? C12 C13 1.554(3) . ? C1A C4A 1.401(3) . ? C5A C11A 1.427(2) . ? C6A C10A 1.430(2) . ? 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 C1A C1 C2 118.4(2) . . ? C3 C2 C1 121.08(19) . . ? C2 C3 C4 121.0(2) . . ? C4A C4 C3 118.1(2) . . ? C4A C5 C5A 107.90(15) . . ? C4A C5 C13 96.09(15) . . ? C5A C5 C13 96.41(15) . . ? C5A C6 C6A 119.23(17) . . ? C8 C7 C6A 121.30(18) . . ? C7 C8 C9 120.11(18) . . ? C10 C9 C8 120.35(18) . . ? C9 C10 C10A 121.20(18) . . ? C11A C11 C10A 119.29(16) . . ? C11A C12 C1A 108.78(15) . . ? C11A C12 C13 96.01(14) . . ? C1A C12 C13 96.16(14) . . ? O1 C13 C12 131.42(19) . . ? O1 C13 C5 131.8(2) . . ? C12 C13 C5 96.78(16) . . ? C1 C1A C4A 120.29(18) . . ? C1 C1A C12 131.76(18) . . ? C4A C1A C12 107.91(16) . . ? C4 C4A C1A 121.07(19) . . ? C4 C4A C5 131.13(18) . . ? C1A C4A C5 107.76(16) . . ? C6 C5A C11A 121.26(17) . . ? C6 C5A C5 131.82(17) . . ? C11A C5A C5 106.83(15) . . ? C7 C6A C6 121.72(17) . . ? C7 C6A C10A 118.67(17) . . ? C6 C6A C10A 119.61(16) . . ? C10 C10A C11 122.02(17) . . ? C10 C10A C6A 118.37(16) . . ? C11 C10A C6A 119.59(16) . . ? C11 C11A C5A 120.93(17) . . ? C11 C11A C12 131.23(16) . . ? C5A C11A C12 107.71(15) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.220 _refine_diff_density_min -0.212 _refine_diff_density_rms 0.088