# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2004 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'Janet Scott' 'Koichi Tanaka' 'Tomohiko Yamada' _publ_contact_author_name 'Dr Janet Scott' _publ_contact_author_address ; Centre for Green Chemistry Monash University P.O. Box 23 Monash University Victoria 3800 AUSTRALIA ; _publ_contact_author_email JANET.SCOTT@SCI.MONASH.EDU.AU _publ_requested_journal 'New Journal of Chemistry' _publ_section_title ; Solid-state Fluorescence Mediated by Guest Inclusion ; data_compound_1 _database_code_depnum_ccdc_archive 'CCDC 222970' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,7-bis-(3-hydroxy-3,3-diphenyl-prop-1-ynyl)-fluoren-9-one pyridine solvate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C43 H28 O3 . 2(C5 H5 N)' _chemical_formula_sum 'C53 H38 N2 O3' _chemical_formula_weight 750.85 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' N N 0.0061 0.0033 '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 Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 18.3759(4) _cell_length_b 25.4454(8) _cell_length_c 8.7400(2) _cell_angle_alpha 90.00 _cell_angle_beta 97.257(2) _cell_angle_gamma 90.00 _cell_volume 4053.93(18) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _exptl_crystal_description needles _exptl_crystal_colour 'bright yellow' _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.230 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1576 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9666 _exptl_absorpt_correction_T_max 0.9776 _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 'Enraf Nonius Kappa CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_number 18359 _diffrn_reflns_av_R_equivalents 0.0931 _diffrn_reflns_av_sigmaI/netI 0.1369 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 28.25 _reflns_number_total 9808 _reflns_number_gt 4647 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement 'Nonius Collect' _computing_data_reduction 'Nonius Collect' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XSeed _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^)+(0.0720P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9808 _refine_ls_number_parameters 531 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1746 _refine_ls_R_factor_gt 0.0687 _refine_ls_wR_factor_ref 0.1723 _refine_ls_wR_factor_gt 0.1377 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 O2 O 1.19311(9) 0.36784(6) 0.24381(18) 0.0285(4) Uani 1 1 d . . . O1 O 0.80549(9) 0.32743(6) 0.73491(16) 0.0298(4) Uani 1 1 d . . . C2 C 0.98800(12) 0.29901(9) 0.4492(2) 0.0204(5) Uani 1 1 d . . . C1 C 0.93273(12) 0.31625(9) 0.5346(2) 0.0221(5) Uani 1 1 d . . . H1 H 0.9252 0.3526 0.5511 0.026 Uiso 1 1 calc R . . C10 C 0.88971(11) 0.27885(9) 0.5935(2) 0.0200(5) Uani 1 1 d . . . C13 C 0.80272(12) 0.23202(9) 0.7188(2) 0.0211(5) Uani 1 1 d . . . C8 C 0.74889(12) 0.21604(9) 0.8057(2) 0.0224(5) Uani 1 1 d . . . H8 H 0.7219 0.2411 0.8561 0.027 Uiso 1 1 calc R . . C12 C 0.84397(12) 0.19570(9) 0.6451(2) 0.0203(5) Uani 1 1 d . . . C24 C 0.68012(13) 0.14385(9) 0.9094(2) 0.0249(5) Uani 1 1 d . . . C25 C 0.63505(13) 0.12854(10) 0.9859(3) 0.0286(6) Uani 1 1 d . . . C7 C 0.73495(12) 0.16224(10) 0.8181(2) 0.0238(5) Uani 1 1 d . . . C6 C 0.77483(13) 0.12610(10) 0.7393(2) 0.0275(6) Uani 1 1 d . . . H6 H 0.7643 0.0897 0.7452 0.033 Uiso 1 1 calc R . . C11 C 0.89895(12) 0.22504(9) 0.5691(2) 0.0200(5) Uani 1 1 d . . . C21 C 1.03452(13) 0.33629(9) 0.3830(2) 0.0235(5) Uani 1 1 d . . . C5 C 0.82916(13) 0.14255(9) 0.6535(2) 0.0267(6) Uani 1 1 d . . . H5 H 0.8558 0.1177 0.6013 0.032 Uiso 1 1 calc R . . C9 C 0.82858(12) 0.28628(9) 0.6901(2) 0.0217(5) Uani 1 1 d . . . C41 C 1.09060(13) 0.40210(9) 0.0761(2) 0.0226(5) Uani 1 1 d . . . C3 C 0.99801(12) 0.24531(9) 0.4273(2) 0.0238(5) Uani 1 1 d . . . H3 H 1.0360 0.2340 0.3707 0.029 Uiso 1 1 calc R . . C22 C 1.07489(13) 0.36495(9) 0.3264(2) 0.0242(5) Uani 1 1 d . . . O3 O 0.58269(10) 0.05201(7) 1.0834(2) 0.0470(5) Uani 1 1 d . . . C42 C 1.02483(13) 0.42922(9) 0.0452(2) 0.0272(6) Uani 1 1 d . . . H42 H 1.0023 0.4434 0.1282 0.033 Uiso 1 1 calc R . . C44 C 1.02476(14) 0.41582(10) -0.2249(3) 0.0327(6) Uani 1 1 d . . . H44 H 1.0027 0.4208 -0.3282 0.039 Uiso 1 1 calc R . . C23 C 1.12600(12) 0.39608(9) 0.2442(2) 0.0226(5) Uani 1 1 d . . . C26 C 0.57336(13) 0.10688(10) 1.0623(3) 0.0302(6) Uani 1 1 d . . . C31 C 1.14184(12) 0.45082(9) 0.3133(2) 0.0229(5) Uani 1 1 d . . . C4 C 0.95401(12) 0.20784(9) 0.4860(2) 0.0234(5) Uani 1 1 d . . . H4 H 0.9614 0.1714 0.4697 0.028 Uiso 1 1 calc R . . C51 C 0.50214(13) 0.12033(11) 0.9577(2) 0.0316(6) Uani 1 1 d . . . C33 C 1.12644(15) 0.52113(11) 0.4912(3) 0.0377(7) Uani 1 1 d . . . H33 H 1.1046 0.5341 0.5766 0.045 Uiso 1 1 calc R . . C46 C 1.12312(14) 0.38138(9) -0.0455(2) 0.0305(6) Uani 1 1 d . . . H46 H 1.1679 0.3624 -0.0260 0.037 Uiso 1 1 calc R . . C32 C 1.10986(14) 0.47031(10) 0.4363(2) 0.0311(6) Uani 1 1 d . . . H32 H 1.0765 0.4492 0.4838 0.037 Uiso 1 1 calc R . . C34 C 1.17371(14) 0.55235(10) 0.4233(3) 0.0370(7) Uani 1 1 d . . . H34 H 1.1843 0.5870 0.4603 0.044 Uiso 1 1 calc R . . C36 C 1.18991(14) 0.48304(10) 0.2463(3) 0.0346(6) Uani 1 1 d . . . H36 H 1.2122 0.4703 0.1613 0.042 Uiso 1 1 calc R . . C43 C 0.99160(14) 0.43595(9) -0.1045(3) 0.0310(6) Uani 1 1 d . . . H43 H 0.9463 0.4543 -0.1242 0.037 Uiso 1 1 calc R . . C45 C 1.08986(15) 0.38855(10) -0.1956(3) 0.0366(7) Uani 1 1 d . . . H45 H 1.1122 0.3745 -0.2791 0.044 Uiso 1 1 calc R . . C61 C 0.57117(13) 0.12965(10) 1.2242(3) 0.0330(6) Uani 1 1 d . . . C35 C 1.20603(14) 0.53315(11) 0.3002(3) 0.0393(7) Uani 1 1 d . . . H35 H 1.2393 0.5545 0.2528 0.047 Uiso 1 1 calc R . . C52 C 0.45090(16) 0.08178(13) 0.9098(3) 0.0514(8) Uani 1 1 d . . . H52 H 0.4598 0.0464 0.9418 0.062 Uiso 1 1 calc R . . C56 C 0.48825(14) 0.17122(13) 0.9086(3) 0.0432(7) Uani 1 1 d . . . H56 H 0.5226 0.1981 0.9415 0.052 Uiso 1 1 calc R . . C66 C 0.62716(16) 0.15827(13) 1.2991(3) 0.0518(8) Uani 1 1 d . . . H66 H 0.6685 0.1665 1.2485 0.062 Uiso 1 1 calc R . . C63 C 0.51017(18) 0.13312(17) 1.4516(3) 0.0751(12) Uani 1 1 d . . . H63 H 0.4702 0.1232 1.5047 0.090 Uiso 1 1 calc R . . C65 C 0.6244(2) 0.17558(14) 1.4494(3) 0.0670(11) Uani 1 1 d . . . H65 H 0.6641 0.1954 1.5005 0.080 Uiso 1 1 calc R . . C62 C 0.51275(17) 0.11624(14) 1.3027(3) 0.0635(10) Uani 1 1 d . . . H62 H 0.4741 0.0952 1.2532 0.076 Uiso 1 1 calc R . . C64 C 0.56547(18) 0.16435(15) 1.5238(3) 0.0644(10) Uani 1 1 d . . . H64 H 0.5625 0.1779 1.6242 0.077 Uiso 1 1 calc R . . C54 C 0.37400(18) 0.1447(2) 0.7656(3) 0.0795(14) Uani 1 1 d . . . H54 H 0.3305 0.1530 0.6993 0.095 Uiso 1 1 calc R . . C55 C 0.42494(17) 0.18370(16) 0.8120(3) 0.0663(11) Uani 1 1 d . . . H55 H 0.4164 0.2188 0.7776 0.080 Uiso 1 1 calc R . . C53 C 0.38692(18) 0.0944(2) 0.8159(4) 0.0742(12) Uani 1 1 d . . . H53 H 0.3517 0.0678 0.7862 0.089 Uiso 1 1 calc R . . N2G N 1.24093(12) 0.33073(9) 0.5441(2) 0.0371(6) Uani 1 1 d . . . C11G C 1.20001(15) 0.29407(11) 0.6002(3) 0.0401(7) Uani 1 1 d . . . H11G H 1.1548 0.2850 0.5410 0.048 Uiso 1 1 calc R . . C10G C 1.21858(15) 0.26870(11) 0.7366(3) 0.0434(7) Uani 1 1 d . . . H10G H 1.1876 0.2423 0.7700 0.052 Uiso 1 1 calc R . . C7G C 1.30383(18) 0.34181(13) 0.6286(3) 0.0568(9) Uani 1 1 d . . . H7G H 1.3352 0.3670 0.5906 0.068 Uiso 1 1 calc R . . C9G C 1.28284(18) 0.28206(14) 0.8248(3) 0.0635(10) Uani 1 1 d . . . H9G H 1.2966 0.2661 0.9224 0.076 Uiso 1 1 calc R . . C8G C 1.3263(2) 0.31860(15) 0.7694(4) 0.0812(13) Uani 1 1 d . . . H8G H 1.3717 0.3282 0.8268 0.097 Uiso 1 1 calc R . . N1G N 0.62525(15) 0.00964(10) 0.8181(3) 0.0553(7) Uani 1 1 d . . . C6G C 0.68644(19) -0.01780(13) 0.8232(4) 0.0629(9) Uani 1 1 d . . . H6G H 0.7121 -0.0261 0.9215 0.075 Uiso 1 1 calc R . . C3G C 0.6146(3) 0.0073(3) 0.5467(5) 0.142(2) Uani 1 1 d . . . H3G H 0.5884 0.0172 0.4503 0.170 Uiso 1 1 calc R . . C5G C 0.7147(2) -0.0347(2) 0.6964(5) 0.1051(16) Uani 1 1 d . . . H5G H 0.7590 -0.0545 0.7049 0.126 Uiso 1 1 calc R . . C2G C 0.5911(2) 0.02218(18) 0.6839(5) 0.0948(14) Uani 1 1 d . . . H2G H 0.5477 0.0427 0.6801 0.114 Uiso 1 1 calc R . . C4G C 0.6772(3) -0.0223(3) 0.5547(5) 0.139(2) Uani 1 1 d . . . H4G H 0.6946 -0.0342 0.4629 0.167 Uiso 1 1 calc R . . H2O H 1.2129(15) 0.3584(12) 0.357(3) 0.075(10) Uiso 1 1 d . . . H3O H 0.5960(17) 0.0353(13) 0.979(4) 0.085(11) Uiso 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 O2 0.0248(10) 0.0326(10) 0.0288(9) 0.0039(7) 0.0061(7) 0.0045(8) O1 0.0312(10) 0.0254(10) 0.0339(9) -0.0003(7) 0.0084(8) 0.0031(8) C2 0.0182(13) 0.0250(14) 0.0176(11) 0.0031(9) 0.0005(9) -0.0033(10) C1 0.0230(14) 0.0194(13) 0.0229(12) 0.0021(9) -0.0006(10) -0.0034(10) C10 0.0165(13) 0.0240(14) 0.0183(11) 0.0022(9) -0.0021(9) 0.0017(10) C13 0.0211(13) 0.0246(14) 0.0171(11) 0.0018(9) 0.0000(10) -0.0013(11) C8 0.0172(13) 0.0289(15) 0.0207(11) 0.0015(10) 0.0008(9) 0.0014(11) C12 0.0196(13) 0.0219(13) 0.0188(11) 0.0046(9) 0.0002(9) -0.0003(10) C24 0.0221(14) 0.0278(14) 0.0248(12) 0.0031(10) 0.0033(11) -0.0011(11) C25 0.0262(15) 0.0318(15) 0.0279(13) 0.0039(11) 0.0036(11) 0.0001(12) C7 0.0179(13) 0.0314(15) 0.0214(11) 0.0038(10) 0.0001(10) -0.0011(11) C6 0.0317(15) 0.0233(14) 0.0282(12) 0.0023(10) 0.0070(11) -0.0043(11) C11 0.0180(13) 0.0240(14) 0.0174(11) 0.0050(9) -0.0009(9) -0.0022(10) C21 0.0251(14) 0.0239(14) 0.0211(12) -0.0001(10) 0.0011(10) -0.0009(11) C5 0.0293(15) 0.0232(14) 0.0290(12) 0.0011(10) 0.0096(11) 0.0018(11) C9 0.0205(13) 0.0260(15) 0.0176(11) 0.0018(10) -0.0010(9) -0.0010(11) C41 0.0233(14) 0.0187(13) 0.0263(12) 0.0011(10) 0.0050(10) -0.0050(11) C3 0.0208(13) 0.0289(15) 0.0219(12) 0.0024(10) 0.0038(10) 0.0003(11) C22 0.0253(14) 0.0241(14) 0.0226(12) -0.0003(10) 0.0004(10) -0.0005(11) O3 0.0514(14) 0.0331(12) 0.0611(12) 0.0101(9) 0.0257(10) -0.0015(10) C42 0.0310(15) 0.0262(14) 0.0245(13) -0.0026(10) 0.0042(11) -0.0012(12) C44 0.0393(17) 0.0349(16) 0.0223(13) 0.0027(11) -0.0019(11) -0.0104(13) C23 0.0192(13) 0.0256(14) 0.0237(12) 0.0033(10) 0.0052(10) -0.0001(11) C26 0.0252(15) 0.0289(15) 0.0381(14) 0.0041(11) 0.0106(11) -0.0046(12) C31 0.0203(13) 0.0250(14) 0.0229(12) 0.0019(10) 0.0007(10) -0.0032(11) C4 0.0243(14) 0.0211(13) 0.0250(12) 0.0018(10) 0.0037(10) -0.0003(11) C51 0.0231(15) 0.0474(19) 0.0262(13) -0.0045(12) 0.0105(11) -0.0062(13) C33 0.0466(18) 0.0373(17) 0.0292(13) -0.0077(12) 0.0048(12) 0.0021(14) C46 0.0332(15) 0.0323(16) 0.0271(13) -0.0017(10) 0.0079(11) 0.0008(12) C32 0.0387(16) 0.0270(15) 0.0288(13) 0.0007(11) 0.0089(11) -0.0037(12) C34 0.0407(17) 0.0266(15) 0.0405(15) -0.0046(12) -0.0075(13) -0.0032(13) C36 0.0313(15) 0.0347(16) 0.0397(14) -0.0056(12) 0.0112(12) -0.0107(13) C43 0.0306(15) 0.0270(15) 0.0338(14) 0.0025(11) -0.0022(11) -0.0031(12) C45 0.0432(18) 0.0420(17) 0.0259(14) -0.0050(11) 0.0097(12) -0.0012(14) C61 0.0228(15) 0.0469(18) 0.0294(13) 0.0097(12) 0.0041(11) -0.0017(13) C35 0.0383(17) 0.0346(17) 0.0447(16) 0.0017(13) 0.0041(13) -0.0132(13) C52 0.0336(18) 0.071(2) 0.0520(17) -0.0216(15) 0.0142(14) -0.0212(16) C56 0.0256(16) 0.066(2) 0.0390(15) 0.0066(14) 0.0065(12) 0.0018(15) C66 0.052(2) 0.073(2) 0.0323(15) 0.0021(14) 0.0143(14) -0.0257(17) C63 0.039(2) 0.154(4) 0.0340(18) 0.0079(19) 0.0105(15) -0.005(2) C65 0.080(3) 0.091(3) 0.0304(16) -0.0003(15) 0.0096(16) -0.037(2) C62 0.0378(19) 0.118(3) 0.0361(17) -0.0007(16) 0.0093(14) -0.0199(19) C64 0.058(2) 0.108(3) 0.0277(15) -0.0006(16) 0.0086(16) -0.002(2) C54 0.0237(19) 0.186(5) 0.0301(17) 0.003(2) 0.0068(14) 0.002(3) C55 0.035(2) 0.115(3) 0.0516(19) 0.0336(19) 0.0147(16) 0.023(2) C53 0.032(2) 0.142(4) 0.050(2) -0.036(2) 0.0106(17) -0.026(2) N2G 0.0392(15) 0.0420(14) 0.0307(12) 0.0025(10) 0.0070(11) 0.0036(12) C11G 0.0384(17) 0.0440(19) 0.0376(15) 0.0026(13) 0.0039(13) 0.0048(14) C10G 0.0424(19) 0.0426(19) 0.0458(16) 0.0123(14) 0.0083(14) 0.0033(14) C7G 0.068(2) 0.061(2) 0.0406(17) 0.0113(15) 0.0027(16) -0.0236(18) C9G 0.058(2) 0.084(3) 0.0468(18) 0.0327(17) -0.0001(16) -0.007(2) C8G 0.071(3) 0.114(3) 0.052(2) 0.032(2) -0.0182(18) -0.045(2) N1G 0.0615(19) 0.0482(18) 0.0591(17) -0.0027(13) 0.0188(14) -0.0053(14) C6G 0.050(2) 0.059(2) 0.080(2) -0.0262(18) 0.0108(18) -0.0040(18) C3G 0.092(4) 0.268(8) 0.069(3) -0.006(3) 0.026(3) -0.009(4) C5G 0.055(3) 0.148(4) 0.116(3) -0.077(3) 0.027(3) -0.008(3) C2G 0.075(3) 0.138(4) 0.076(3) 0.008(3) 0.028(2) 0.017(3) C4G 0.076(3) 0.264(7) 0.087(3) -0.083(4) 0.051(3) -0.038(4) _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 O2 C23 1.428(3) . ? O1 C9 1.213(3) . ? C2 C3 1.395(3) . ? C2 C1 1.404(3) . ? C2 C21 1.446(3) . ? C1 C10 1.378(3) . ? C10 C11 1.399(3) . ? C10 C9 1.500(3) . ? C13 C8 1.382(3) . ? C13 C12 1.403(3) . ? C13 C9 1.492(3) . ? C8 C7 1.399(3) . ? C12 C5 1.384(3) . ? C12 C11 1.479(3) . ? C24 C25 1.194(3) . ? C24 C7 1.440(3) . ? C25 C26 1.492(3) . ? C7 C6 1.408(3) . ? C6 C5 1.387(3) . ? C11 C4 1.389(3) . ? C21 C22 1.192(3) . ? C41 C46 1.387(3) . ? C41 C42 1.388(3) . ? C41 C23 1.538(3) . ? C3 C4 1.389(3) . ? C22 C23 1.482(3) . ? O3 C26 1.416(3) . ? C42 C43 1.383(3) . ? C44 C45 1.379(3) . ? C44 C43 1.380(3) . ? C23 C31 1.532(3) . ? C26 C61 1.534(3) . ? C26 C51 1.537(3) . ? C31 C32 1.381(3) . ? C31 C36 1.388(3) . ? C51 C56 1.378(4) . ? C51 C52 1.387(3) . ? C33 C34 1.367(3) . ? C33 C32 1.399(3) . ? C46 C45 1.388(3) . ? C34 C35 1.382(3) . ? C36 C35 1.379(3) . ? C61 C66 1.359(4) . ? C61 C62 1.388(3) . ? C52 C53 1.384(4) . ? C56 C55 1.385(4) . ? C66 C65 1.392(4) . ? C63 C62 1.377(4) . ? C63 C64 1.378(4) . ? C65 C64 1.363(4) . ? C54 C53 1.366(5) . ? C54 C55 1.389(5) . ? N2G C7G 1.321(3) . ? N2G C11G 1.330(3) . ? C11G C10G 1.361(3) . ? C10G C9G 1.369(4) . ? C7G C8G 1.380(4) . ? C9G C8G 1.354(4) . ? N1G C2G 1.298(4) . ? N1G C6G 1.319(4) . ? C6G C5G 1.353(4) . ? C3G C4G 1.369(7) . ? C3G C2G 1.378(5) . ? C5G C4G 1.376(6) . ? 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 C3 C2 C1 119.7(2) . . ? C3 C2 C21 119.5(2) . . ? C1 C2 C21 120.8(2) . . ? C10 C1 C2 118.1(2) . . ? C1 C10 C11 122.2(2) . . ? C1 C10 C9 129.0(2) . . ? C11 C10 C9 108.84(19) . . ? C8 C13 C12 121.6(2) . . ? C8 C13 C9 129.0(2) . . ? C12 C13 C9 109.29(19) . . ? C13 C8 C7 118.7(2) . . ? C5 C12 C13 119.9(2) . . ? C5 C12 C11 131.9(2) . . ? C13 C12 C11 108.2(2) . . ? C25 C24 C7 179.5(3) . . ? C24 C25 C26 172.5(2) . . ? C8 C7 C6 119.3(2) . . ? C8 C7 C24 120.5(2) . . ? C6 C7 C24 120.1(2) . . ? C5 C6 C7 121.4(2) . . ? C4 C11 C10 119.9(2) . . ? C4 C11 C12 131.3(2) . . ? C10 C11 C12 108.82(19) . . ? C22 C21 C2 176.7(3) . . ? C12 C5 C6 118.9(2) . . ? O1 C9 C13 127.8(2) . . ? O1 C9 C10 127.4(2) . . ? C13 C9 C10 104.78(19) . . ? C46 C41 C42 119.3(2) . . ? C46 C41 C23 121.5(2) . . ? C42 C41 C23 119.20(19) . . ? C4 C3 C2 121.9(2) . . ? C21 C22 C23 173.9(2) . . ? C43 C42 C41 121.0(2) . . ? C45 C44 C43 120.1(2) . . ? O2 C23 C22 109.43(18) . . ? O2 C23 C31 109.72(18) . . ? C22 C23 C31 113.29(18) . . ? O2 C23 C41 108.02(17) . . ? C22 C23 C41 107.40(18) . . ? C31 C23 C41 108.84(18) . . ? O3 C26 C25 109.6(2) . . ? O3 C26 C61 105.63(18) . . ? C25 C26 C61 112.5(2) . . ? O3 C26 C51 112.1(2) . . ? C25 C26 C51 106.83(18) . . ? C61 C26 C51 110.2(2) . . ? C32 C31 C36 118.2(2) . . ? C32 C31 C23 123.7(2) . . ? C36 C31 C23 118.0(2) . . ? C11 C4 C3 118.2(2) . . ? C56 C51 C52 118.6(3) . . ? C56 C51 C26 120.3(2) . . ? C52 C51 C26 121.1(3) . . ? C34 C33 C32 120.7(2) . . ? C41 C46 C45 119.6(2) . . ? C31 C32 C33 120.2(2) . . ? C33 C34 C35 119.5(2) . . ? C35 C36 C31 121.5(2) . . ? C44 C43 C42 119.4(2) . . ? C44 C45 C46 120.6(2) . . ? C66 C61 C62 118.6(2) . . ? C66 C61 C26 122.7(2) . . ? C62 C61 C26 118.4(2) . . ? C36 C35 C34 119.9(2) . . ? C53 C52 C51 120.6(3) . . ? C51 C56 C55 120.9(3) . . ? C61 C66 C65 120.6(3) . . ? C62 C63 C64 120.1(3) . . ? C64 C65 C66 120.6(3) . . ? C63 C62 C61 120.8(3) . . ? C65 C64 C63 119.2(3) . . ? C53 C54 C55 119.5(3) . . ? C56 C55 C54 119.8(3) . . ? C54 C53 C52 120.5(4) . . ? C7G N2G C11G 116.0(2) . . ? N2G C11G C10G 124.4(3) . . ? C11G C10G C9G 118.6(3) . . ? N2G C7G C8G 123.3(3) . . ? C8G C9G C10G 118.4(3) . . ? C9G C8G C7G 119.3(3) . . ? C2G N1G C6G 118.2(3) . . ? N1G C6G C5G 123.7(4) . . ? C4G C3G C2G 117.4(4) . . ? C6G C5G C4G 117.6(4) . . ? N1G C2G C3G 123.4(4) . . ? C3G C4G C5G 119.6(4) . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 28.25 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.374 _refine_diff_density_min -0.383 _refine_diff_density_rms 0.060 data_compound_2 _database_code_depnum_ccdc_archive 'CCDC 222971' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,7-bis-(3-hydroxy-3,3-diphenyl-prop-1-ynyl)-fluoren-9-one 3-acetylpyridine solvate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C43 H28 O3 . C7 H7 N1 O1' _chemical_formula_sum 'C50 H35 N O4' _chemical_formula_weight 713.79 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' N N 0.0061 0.0033 '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 Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 16.9301(4) _cell_length_b 8.5045(2) _cell_length_c 25.5885(6) _cell_angle_alpha 90.00 _cell_angle_beta 92.5690(10) _cell_angle_gamma 90.00 _cell_volume 3680.58(15) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _exptl_crystal_description 'thin plates' _exptl_crystal_colour yellow/orange _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.288 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1496 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9761 _exptl_absorpt_correction_T_max 0.9919 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 'Enraf Nonius Kappa CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_number 9007 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1664 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 2.78 _diffrn_reflns_theta_max 28.27 _reflns_number_total 9007 _reflns_number_gt 4139 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement 'Nonius Collect' _computing_data_reduction 'Nonius Collect' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XSeed _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^)+(0.0472P)^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 mixed _refine_ls_extinction_method none _refine_ls_number_reflns 9007 _refine_ls_number_parameters 505 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1821 _refine_ls_R_factor_gt 0.0606 _refine_ls_wR_factor_ref 0.1266 _refine_ls_wR_factor_gt 0.0974 _refine_ls_goodness_of_fit_ref 0.962 _refine_ls_restrained_S_all 0.962 _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 O2 O 0.26227(10) 0.10277(19) 0.15714(5) 0.0259(4) Uani 1 1 d . . . O1 O 0.59746(9) 0.42361(18) 0.34278(5) 0.0307(4) Uani 1 1 d . . . O3 O 0.75904(10) 1.01287(18) 0.61436(5) 0.0275(4) Uani 1 1 d . . . C8 C 0.61358(13) 0.6472(2) 0.43999(7) 0.0198(5) Uani 1 1 d . . . H8 H 0.6650 0.6321 0.4274 0.024 Uiso 1 1 calc R . . C12 C 0.47279(12) 0.5909(2) 0.43490(7) 0.0162(5) Uani 1 1 d . . . C21 C 0.66602(14) 0.8305(2) 0.50860(8) 0.0210(5) Uani 1 1 d . . . C51 C 0.13894(13) 0.1797(2) 0.19202(7) 0.0185(5) Uani 1 1 d . . . C7 C 0.60167(13) 0.7477(2) 0.48228(7) 0.0193(5) Uani 1 1 d . . . C46 C 0.88829(14) 0.8363(2) 0.60871(8) 0.0252(6) Uani 1 1 d . . . H46 H 0.8607 0.8482 0.6400 0.030 Uiso 1 1 calc R . . C11 C 0.41657(13) 0.4961(2) 0.40204(7) 0.0171(5) Uani 1 1 d . . . C56 C 0.08549(13) 0.1903(2) 0.23163(8) 0.0232(5) Uani 1 1 d . . . H56 H 0.0979 0.1427 0.2646 0.028 Uiso 1 1 calc R . . C61 C 0.19896(12) -0.0810(2) 0.21483(8) 0.0191(5) Uani 1 1 d . . . C23 C 0.77948(13) 0.9940(2) 0.56126(7) 0.0201(5) Uani 1 1 d . . . C22 C 0.71685(14) 0.9011(3) 0.53201(8) 0.0222(5) Uani 1 1 d . . . C6 C 0.52477(13) 0.7692(2) 0.49930(8) 0.0227(5) Uani 1 1 d . . . H6 H 0.5167 0.8390 0.5275 0.027 Uiso 1 1 calc R . . C5 C 0.46015(13) 0.6914(2) 0.47608(7) 0.0221(5) Uani 1 1 d . . . H5 H 0.4085 0.7070 0.4882 0.026 Uiso 1 1 calc R . . C3 C 0.29688(13) 0.3935(2) 0.36342(8) 0.0218(5) Uani 1 1 d . . . H3 H 0.2409 0.3840 0.3631 0.026 Uiso 1 1 calc R . . C10 C 0.45879(13) 0.4182(2) 0.36401(7) 0.0187(5) Uani 1 1 d . . . C54 C -0.00408(14) 0.3370(3) 0.17554(8) 0.0296(6) Uani 1 1 d . . . H54 H -0.0528 0.3912 0.1699 0.036 Uiso 1 1 calc R . . C32 C 0.75211(13) 1.1972(3) 0.48870(8) 0.0249(6) Uani 1 1 d . . . H32 H 0.7177 1.1244 0.4711 0.030 Uiso 1 1 calc R . . C25 C 0.26116(13) 0.1688(2) 0.24759(8) 0.0211(5) Uani 1 1 d . . . C26 C 0.21685(13) 0.0911(2) 0.20303(7) 0.0191(5) Uani 1 1 d . . . C1 C 0.42107(13) 0.3291(2) 0.32574(8) 0.0217(5) Uani 1 1 d . . . H1 H 0.4506 0.2760 0.3004 0.026 Uiso 1 1 calc R . . C24 C 0.29609(13) 0.2331(2) 0.28298(8) 0.0212(5) Uani 1 1 d . . . C44 C 0.99989(14) 0.7352(3) 0.56448(9) 0.0327(6) Uani 1 1 d . . . H44 H 1.0486 0.6797 0.5651 0.039 Uiso 1 1 calc R . . C31 C 0.78996(13) 1.1557(2) 0.53562(8) 0.0214(5) Uani 1 1 d . . . C13 C 0.54888(13) 0.5703(2) 0.41690(7) 0.0177(5) Uani 1 1 d . . . C41 C 0.85727(13) 0.9011(2) 0.56261(8) 0.0200(5) Uani 1 1 d . . . C9 C 0.54408(14) 0.4615(2) 0.37083(8) 0.0217(5) Uani 1 1 d . . . C2 C 0.33821(13) 0.3175(2) 0.32462(7) 0.0196(5) Uani 1 1 d . . . C36 C 0.84031(13) 1.2643(3) 0.56091(8) 0.0274(6) Uani 1 1 d . . . H36 H 0.8669 1.2375 0.5932 0.033 Uiso 1 1 calc R . . C52 C 0.11961(13) 0.2473(2) 0.14390(8) 0.0237(5) Uani 1 1 d . . . H52 H 0.1553 0.2401 0.1164 0.028 Uiso 1 1 calc R . . C4 C 0.33520(13) 0.4822(2) 0.40232(7) 0.0208(5) Uani 1 1 d . . . H4 H 0.3062 0.5323 0.4286 0.025 Uiso 1 1 calc R . . C66 C 0.16872(13) -0.1747(3) 0.17407(8) 0.0277(6) Uani 1 1 d . . . H66 H 0.1602 -0.1306 0.1402 0.033 Uiso 1 1 calc R . . C45 C 0.95941(15) 0.7540(3) 0.60990(9) 0.0326(6) Uani 1 1 d . . . H45 H 0.9802 0.7108 0.6419 0.039 Uiso 1 1 calc R . . C55 C 0.01498(14) 0.2687(3) 0.22366(8) 0.0294(6) Uani 1 1 d . . . H55 H -0.0207 0.2762 0.2512 0.035 Uiso 1 1 calc R . . C53 C 0.04832(14) 0.3254(3) 0.13591(8) 0.0290(6) Uani 1 1 d . . . H53 H 0.0353 0.3715 0.1028 0.035 Uiso 1 1 calc R . . C43 C 0.96862(15) 0.7977(3) 0.51847(9) 0.0372(7) Uani 1 1 d . . . H43 H 0.9958 0.7840 0.4871 0.045 Uiso 1 1 calc R . . C42 C 0.89829(14) 0.8800(3) 0.51724(8) 0.0303(6) Uani 1 1 d . . . H42 H 0.8777 0.9226 0.4851 0.036 Uiso 1 1 calc R . . C62 C 0.20932(14) -0.1446(3) 0.26409(8) 0.0280(6) Uani 1 1 d . . . H62 H 0.2287 -0.0813 0.2924 0.034 Uiso 1 1 calc R . . C35 C 0.85151(15) 1.4117(3) 0.53891(10) 0.0357(6) Uani 1 1 d . . . H35 H 0.8856 1.4855 0.5563 0.043 Uiso 1 1 calc R . . C63 C 0.19122(14) -0.3029(3) 0.27221(10) 0.0372(7) Uani 1 1 d . . . H63 H 0.1984 -0.3473 0.3062 0.045 Uiso 1 1 calc R . . C34 C 0.81344(15) 1.4513(3) 0.49208(10) 0.0372(7) Uani 1 1 d . . . H34 H 0.8213 1.5521 0.4772 0.045 Uiso 1 1 calc R . . C65 C 0.15100(14) -0.3299(3) 0.18221(10) 0.0378(7) Uani 1 1 d . . . H65 H 0.1305 -0.3926 0.1540 0.045 Uiso 1 1 calc R . . C33 C 0.76408(15) 1.3446(3) 0.46706(9) 0.0337(6) Uani 1 1 d . . . H33 H 0.7379 1.3718 0.4347 0.040 Uiso 1 1 calc R . . C64 C 0.16295(15) -0.3947(3) 0.23103(11) 0.0408(7) Uani 1 1 d . . . H64 H 0.1518 -0.5028 0.2365 0.049 Uiso 1 1 calc R . . O1G O 0.41482(10) 0.8847(2) 0.58820(6) 0.0448(5) Uani 1 1 d . . . N1G N 0.61194(12) 1.1211(2) 0.64719(7) 0.0326(5) Uani 1 1 d . . . C2G C 0.54770(15) 1.0414(3) 0.62959(8) 0.0290(6) Uani 1 1 d . . . H2G H 0.5537 0.9662 0.6026 0.035 Uiso 1 1 calc R . . C3G C 0.47241(14) 1.0630(3) 0.64886(8) 0.0283(6) Uani 1 1 d . . . C5G C 0.53035(15) 1.2542(3) 0.70654(8) 0.0351(6) Uani 1 1 d . . . H5G H 0.5264 1.3299 0.7336 0.042 Uiso 1 1 calc R . . C4G C 0.46371(15) 1.1714(3) 0.68824(8) 0.0323(6) Uani 1 1 d . . . H4G H 0.4136 1.1892 0.7025 0.039 Uiso 1 1 calc R . . C6G C 0.60185(16) 1.2254(3) 0.68509(8) 0.0363(6) Uani 1 1 d . . . H6G H 0.6466 1.2832 0.6980 0.044 Uiso 1 1 calc R . . C7G C 0.40512(15) 0.9704(3) 0.62591(9) 0.0339(6) Uani 1 1 d . . . C8G C 0.32663(15) 0.9838(3) 0.64909(10) 0.0506(8) Uani 1 1 d . . . H8G1 H 0.2885 0.9171 0.6295 0.076 Uiso 1 1 calc R . . H8G2 H 0.3089 1.0934 0.6473 0.076 Uiso 1 1 calc R . . H8G3 H 0.3307 0.9497 0.6857 0.076 Uiso 1 1 calc R . . H3O H 0.7091(17) 1.059(3) 0.6171(10) 0.076(10) Uiso 1 1 d . . . H2O H 0.3030(15) 0.037(3) 0.1602(8) 0.048(8) Uiso 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 O2 0.0230(10) 0.0333(10) 0.0216(8) 0.0015(7) 0.0035(7) 0.0055(9) O1 0.0191(10) 0.0388(10) 0.0346(9) -0.0131(7) 0.0054(8) -0.0026(8) O3 0.0231(11) 0.0407(11) 0.0186(8) -0.0039(7) 0.0020(7) 0.0012(8) C8 0.0157(13) 0.0232(13) 0.0207(11) 0.0021(10) 0.0010(10) -0.0009(10) C12 0.0147(13) 0.0186(12) 0.0152(11) 0.0001(9) -0.0007(9) -0.0038(10) C21 0.0203(14) 0.0229(13) 0.0196(11) -0.0002(10) -0.0024(10) -0.0032(11) C51 0.0172(13) 0.0160(12) 0.0221(12) -0.0036(10) -0.0030(10) -0.0027(10) C7 0.0198(14) 0.0198(12) 0.0177(11) 0.0026(10) -0.0052(10) -0.0054(10) C46 0.0274(16) 0.0255(14) 0.0223(12) -0.0041(10) -0.0026(11) -0.0045(12) C11 0.0181(14) 0.0171(12) 0.0158(11) 0.0019(9) -0.0025(10) -0.0042(10) C56 0.0199(14) 0.0274(14) 0.0222(12) 0.0042(10) -0.0003(10) 0.0002(11) C61 0.0137(13) 0.0186(13) 0.0250(12) -0.0039(10) 0.0004(10) 0.0001(10) C23 0.0175(14) 0.0245(13) 0.0181(11) -0.0054(10) -0.0011(10) -0.0042(11) C22 0.0219(14) 0.0238(13) 0.0207(12) 0.0018(10) 0.0010(10) 0.0017(12) C6 0.0239(15) 0.0254(13) 0.0187(11) -0.0055(10) 0.0008(10) -0.0041(11) C5 0.0160(14) 0.0288(14) 0.0214(12) -0.0005(10) 0.0016(10) -0.0022(11) C3 0.0159(13) 0.0237(13) 0.0255(12) 0.0051(10) -0.0027(10) -0.0034(11) C10 0.0172(13) 0.0193(13) 0.0192(11) -0.0023(10) -0.0020(10) -0.0015(11) C54 0.0213(15) 0.0293(14) 0.0377(14) -0.0024(12) -0.0046(12) 0.0013(11) C32 0.0243(15) 0.0262(14) 0.0243(12) -0.0029(10) 0.0034(11) -0.0020(11) C25 0.0191(14) 0.0204(13) 0.0238(12) 0.0016(10) 0.0006(10) -0.0016(11) C26 0.0184(14) 0.0233(13) 0.0153(11) -0.0016(10) -0.0009(10) -0.0006(11) C1 0.0217(14) 0.0220(13) 0.0212(12) -0.0043(10) 0.0005(10) -0.0007(11) C24 0.0182(14) 0.0208(13) 0.0242(12) 0.0032(10) -0.0028(10) -0.0021(11) C44 0.0186(15) 0.0309(15) 0.0480(16) -0.0028(12) -0.0044(12) 0.0032(12) C31 0.0191(14) 0.0213(13) 0.0240(12) -0.0049(10) 0.0044(10) -0.0019(11) C13 0.0161(13) 0.0183(12) 0.0183(11) 0.0008(9) -0.0027(10) -0.0028(10) C41 0.0169(13) 0.0198(13) 0.0232(12) -0.0046(10) -0.0010(10) -0.0042(10) C9 0.0212(15) 0.0204(13) 0.0231(12) 0.0001(10) -0.0016(11) -0.0020(11) C2 0.0193(14) 0.0184(12) 0.0206(12) 0.0017(10) -0.0035(10) -0.0051(11) C36 0.0203(14) 0.0280(15) 0.0336(13) -0.0062(11) -0.0008(11) -0.0038(12) C52 0.0243(15) 0.0263(14) 0.0202(12) -0.0015(10) -0.0008(10) 0.0010(12) C4 0.0186(14) 0.0242(13) 0.0196(11) -0.0012(10) 0.0007(10) -0.0027(11) C66 0.0239(15) 0.0281(15) 0.0310(13) -0.0096(11) 0.0007(11) -0.0034(12) C45 0.0301(16) 0.0320(15) 0.0344(14) -0.0018(12) -0.0118(12) 0.0011(12) C55 0.0250(15) 0.0336(15) 0.0297(13) -0.0025(11) 0.0035(11) -0.0004(12) C53 0.0293(16) 0.0305(15) 0.0262(12) 0.0021(11) -0.0086(11) 0.0026(12) C43 0.0309(17) 0.0422(16) 0.0394(15) -0.0006(13) 0.0106(13) 0.0047(13) C42 0.0274(16) 0.0359(15) 0.0275(13) 0.0029(11) 0.0021(11) 0.0055(12) C62 0.0280(16) 0.0239(14) 0.0318(13) 0.0011(11) -0.0038(11) -0.0027(11) C35 0.0263(16) 0.0255(15) 0.0560(17) -0.0125(13) 0.0095(13) -0.0074(12) C63 0.0297(17) 0.0320(16) 0.0496(16) 0.0139(13) -0.0011(13) 0.0019(13) C34 0.0358(18) 0.0249(15) 0.0523(17) 0.0039(13) 0.0178(14) 0.0006(13) C65 0.0268(16) 0.0323(17) 0.0541(17) -0.0173(13) 0.0000(13) -0.0045(13) C33 0.0363(18) 0.0285(15) 0.0368(14) 0.0055(12) 0.0085(12) 0.0068(13) C64 0.0276(17) 0.0171(14) 0.078(2) -0.0050(14) 0.0062(15) 0.0005(12) O1G 0.0394(12) 0.0518(12) 0.0436(10) -0.0151(9) 0.0052(9) -0.0052(9) N1G 0.0294(14) 0.0374(13) 0.0305(11) 0.0010(10) -0.0046(10) 0.0013(11) C2G 0.0288(17) 0.0312(15) 0.0271(13) 0.0012(11) 0.0035(12) 0.0060(12) C3G 0.0279(16) 0.0305(15) 0.0264(13) 0.0060(11) -0.0008(11) 0.0011(12) C5G 0.0392(18) 0.0420(16) 0.0243(13) -0.0007(11) 0.0052(12) -0.0030(14) C4G 0.0348(17) 0.0387(16) 0.0238(13) -0.0036(12) 0.0044(11) 0.0023(13) C6G 0.0390(18) 0.0413(17) 0.0284(14) 0.0037(13) -0.0008(12) -0.0010(13) C7G 0.0350(18) 0.0335(16) 0.0331(14) 0.0006(12) 0.0012(12) 0.0028(13) C8G 0.0308(18) 0.063(2) 0.0584(17) -0.0167(15) 0.0113(14) -0.0108(15) _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 O2 C26 1.436(2) . ? O1 C9 1.222(2) . ? O3 C23 1.426(2) . ? C8 C13 1.385(3) . ? C8 C7 1.400(3) . ? C12 C5 1.381(3) . ? C12 C13 1.398(3) . ? C12 C11 1.480(3) . ? C21 C22 1.189(3) . ? C21 C7 1.439(3) . ? C51 C52 1.385(3) . ? C51 C56 1.392(3) . ? C51 C26 1.534(3) . ? C7 C6 1.403(3) . ? C46 C41 1.384(3) . ? C46 C45 1.392(3) . ? C11 C4 1.383(3) . ? C11 C10 1.399(3) . ? C56 C55 1.375(3) . ? C61 C62 1.376(3) . ? C61 C66 1.392(3) . ? C61 C26 1.528(3) . ? C23 C22 1.496(3) . ? C23 C41 1.535(3) . ? C23 C31 1.538(3) . ? C6 C5 1.389(3) . ? C3 C4 1.387(3) . ? C3 C2 1.398(3) . ? C10 C1 1.373(3) . ? C10 C9 1.493(3) . ? C54 C53 1.380(3) . ? C54 C55 1.386(3) . ? C32 C31 1.381(3) . ? C32 C33 1.389(3) . ? C25 C24 1.192(3) . ? C25 C26 1.491(3) . ? C1 C2 1.405(3) . ? C24 C2 1.446(3) . ? C44 C43 1.376(3) . ? C44 C45 1.385(3) . ? C31 C36 1.396(3) . ? C13 C9 1.498(3) . ? C41 C42 1.391(3) . ? C36 C35 1.390(3) . ? C52 C53 1.385(3) . ? C66 C65 1.372(3) . ? C43 C42 1.380(3) . ? C62 C63 1.398(3) . ? C35 C34 1.377(3) . ? C63 C64 1.380(3) . ? C34 C33 1.373(3) . ? C65 C64 1.372(3) . ? O1G C7G 1.226(3) . ? N1G C6G 1.331(3) . ? N1G C2G 1.342(3) . ? C2G C3G 1.399(3) . ? C3G C4G 1.379(3) . ? C3G C7G 1.484(3) . ? C5G C6G 1.373(3) . ? C5G C4G 1.393(3) . ? C7G C8G 1.484(3) . ? 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 C13 C8 C7 118.6(2) . . ? C5 C12 C13 120.37(19) . . ? C5 C12 C11 130.8(2) . . ? C13 C12 C11 108.84(17) . . ? C22 C21 C7 177.0(2) . . ? C52 C51 C56 119.0(2) . . ? C52 C51 C26 122.28(18) . . ? C56 C51 C26 118.68(17) . . ? C8 C7 C6 119.1(2) . . ? C8 C7 C21 121.9(2) . . ? C6 C7 C21 118.98(19) . . ? C41 C46 C45 120.9(2) . . ? C4 C11 C10 120.20(19) . . ? C4 C11 C12 131.21(19) . . ? C10 C11 C12 108.50(18) . . ? C55 C56 C51 120.79(19) . . ? C62 C61 C66 119.3(2) . . ? C62 C61 C26 122.65(18) . . ? C66 C61 C26 118.02(18) . . ? O3 C23 C22 109.84(17) . . ? O3 C23 C41 106.33(16) . . ? C22 C23 C41 109.12(17) . . ? O3 C23 C31 110.09(16) . . ? C22 C23 C31 110.60(17) . . ? C41 C23 C31 110.77(17) . . ? C21 C22 C23 178.4(2) . . ? C5 C6 C7 122.0(2) . . ? C12 C5 C6 118.4(2) . . ? C4 C3 C2 121.9(2) . . ? C1 C10 C11 121.4(2) . . ? C1 C10 C9 129.50(19) . . ? C11 C10 C9 108.87(18) . . ? C53 C54 C55 119.4(2) . . ? C31 C32 C33 120.4(2) . . ? C24 C25 C26 179.0(2) . . ? O2 C26 C25 108.99(17) . . ? O2 C26 C61 110.25(15) . . ? C25 C26 C61 111.76(16) . . ? O2 C26 C51 107.68(16) . . ? C25 C26 C51 108.77(17) . . ? C61 C26 C51 109.29(17) . . ? C10 C1 C2 119.02(19) . . ? C25 C24 C2 177.5(2) . . ? C43 C44 C45 119.2(2) . . ? C32 C31 C36 118.9(2) . . ? C32 C31 C23 122.78(19) . . ? C36 C31 C23 118.28(19) . . ? C8 C13 C12 121.51(18) . . ? C8 C13 C9 129.9(2) . . ? C12 C13 C9 108.57(18) . . ? C46 C41 C42 118.4(2) . . ? C46 C41 C23 121.09(18) . . ? C42 C41 C23 120.52(18) . . ? O1 C9 C10 127.09(18) . . ? O1 C9 C13 127.6(2) . . ? C10 C9 C13 105.22(17) . . ? C3 C2 C1 118.95(19) . . ? C3 C2 C24 120.4(2) . . ? C1 C2 C24 120.58(19) . . ? C35 C36 C31 120.0(2) . . ? C53 C52 C51 120.0(2) . . ? C11 C4 C3 118.48(19) . . ? C65 C66 C61 120.8(2) . . ? C44 C45 C46 120.0(2) . . ? C56 C55 C54 120.1(2) . . ? C54 C53 C52 120.7(2) . . ? C44 C43 C42 120.9(2) . . ? C43 C42 C41 120.6(2) . . ? C61 C62 C63 119.7(2) . . ? C34 C35 C36 120.4(2) . . ? C64 C63 C62 120.2(2) . . ? C33 C34 C35 119.7(2) . . ? C66 C65 C64 120.0(2) . . ? C34 C33 C32 120.5(2) . . ? C65 C64 C63 120.0(2) . . ? C6G N1G C2G 116.9(2) . . ? N1G C2G C3G 123.5(2) . . ? C4G C3G C2G 118.3(2) . . ? C4G C3G C7G 122.6(2) . . ? C2G C3G C7G 119.1(2) . . ? C6G C5G C4G 119.4(2) . . ? C3G C4G C5G 118.2(2) . . ? N1G C6G C5G 123.7(2) . . ? O1G C7G C8G 120.9(2) . . ? O1G C7G C3G 120.0(2) . . ? C8G C7G C3G 119.1(2) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.262 _refine_diff_density_min -0.323 _refine_diff_density_rms 0.058