# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2011 data_global _journal_name_full 'New J.Chem.' _journal_coden_cambridge 0440 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Hong Su' _publ_contact_author_email Hong.Su@uct.ac.za loop_ _publ_author_name S.Bourne K.Corin D.Cruickshank J.Davson L.Nassimbeni H.Su ; E.Weber ; data_h2pic _database_code_depnum_ccdc_archive 'CCDC 817290' #TrackingRef '- H2PIC.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1,4-bis(9-hydroxyfluoren-9-yl)benzene. 2-picoline clathrate' ; _chemical_name_common "'1,4-bis(9-hydroxyfluoren-9-yl)benzene. 2-picoline clathrate'" _chemical_melting_point 264-265 _chemical_formula_moiety 'C32 H22 O2, 2(C6 H7 N)' _chemical_formula_sum 'C44 H36 N2 O2' _chemical_formula_weight 624.75 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 'P 21/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 14.5758(4) _cell_length_b 15.5947(4) _cell_length_c 14.6354(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.9070(10) _cell_angle_gamma 90.00 _cell_volume 3326.29(15) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3861 _cell_measurement_theta_min 1.9 _cell_measurement_theta_max 25.6 _exptl_crystal_description 'clear blocks' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.248 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1320 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type none _exptl_special_details ; Distances of O1X-H1OX and O1Y-H1OY are restarinted to 0.97(2)angstroms; ditance of C6G2-C8G2 is restrainted to 1.43(2) angstroms; distance of C8G2-C5G2 is restrainted to 2.54(3) angstroms. ; _diffrn_ambient_temperature 173(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 Kappa CCD' _diffrn_measurement_method 'Combination of phi and omega' _diffrn_reflns_number 11735 _diffrn_reflns_av_R_equivalents 0.0572 _diffrn_reflns_av_sigmaI/netI 0.0855 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.80 _diffrn_reflns_theta_max 25.65 _reflns_number_total 6205 _reflns_number_gt 3854 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 2000)' _computing_cell_refinement 'Collect (Nonius, 2000)' _computing_data_reduction 'Collect (Nonius, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSEED, graphical interface to SHELX (1999)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1064P)^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 none _refine_ls_number_reflns 6205 _refine_ls_number_parameters 451 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.1071 _refine_ls_R_factor_gt 0.0615 _refine_ls_wR_factor_ref 0.1787 _refine_ls_wR_factor_gt 0.1563 _refine_ls_goodness_of_fit_ref 0.991 _refine_ls_restrained_S_all 1.017 _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 C1AX C 0.24606(16) -0.01816(14) 0.03728(15) 0.0298(6) Uani 1 1 d . . . C4AX C 0.17398(17) 0.00950(14) -0.02007(15) 0.0307(6) Uani 1 1 d . . . C5AX C 0.19095(17) 0.09952(15) -0.04497(15) 0.0301(6) Uani 1 1 d . . . C8AX C 0.27319(17) 0.12621(14) -0.00290(15) 0.0297(6) Uani 1 1 d . . . C1AY C 0.76394(16) 0.08257(14) 0.52981(15) 0.0293(6) Uani 1 1 d . . . C4AY C 0.68523(17) 0.03191(15) 0.53688(17) 0.0354(6) Uani 1 1 d . . . C5AY C 0.67844(17) -0.02317(15) 0.45605(17) 0.0346(6) Uani 1 1 d . . . C8AY C 0.75494(17) -0.00875(14) 0.40086(16) 0.0316(6) Uani 1 1 d . . . N1G1 N 0.14471(14) 0.14172(13) 0.18377(13) 0.0343(5) Uani 1 1 d . . . C2G1 C 0.07713(18) 0.09897(16) 0.22604(15) 0.0336(6) Uani 1 1 d . . . C3G1 C -0.00554(18) 0.13833(17) 0.24510(16) 0.0380(6) Uani 1 1 d . . . H3G1 H -0.0525 0.1069 0.2743 0.046 Uiso 1 1 calc R . . C4G1 C -0.01995(19) 0.22262(17) 0.22196(16) 0.0402(7) Uani 1 1 d . . . H4G1 H -0.0761 0.2503 0.2358 0.048 Uiso 1 1 calc R . . C5G1 C 0.04896(19) 0.26612(17) 0.17815(16) 0.0415(7) Uani 1 1 d . . . H5G1 H 0.0412 0.3243 0.1606 0.050 Uiso 1 1 calc R . . C6G1 C 0.12972(19) 0.22305(16) 0.16038(16) 0.0383(7) Uani 1 1 d . . . H6G1 H 0.1770 0.2531 0.1299 0.046 Uiso 1 1 calc R . . C7G1 C 0.0967(2) 0.00708(16) 0.25084(18) 0.0494(7) Uani 1 1 d . . . H7G1 H 0.0935 -0.0285 0.1956 0.074 Uiso 1 1 calc R . . H7G2 H 0.0511 -0.0130 0.2945 0.074 Uiso 1 1 calc R . . H7G3 H 0.1582 0.0028 0.2785 0.074 Uiso 1 1 calc R . . N1G2 N 0.65574(15) 0.17958(12) 0.32804(14) 0.0355(5) Uani 1 1 d . . . C2G2 C 0.6244(2) 0.15473(16) 0.2457(2) 0.0513(8) Uani 1 1 d . . . C3G2 C 0.5228(3) 0.1615(2) 0.2279(3) 0.0775(13) Uani 1 1 d . . . H3G2 H 0.4956 0.1453 0.1710 0.093 Uiso 1 1 calc R . . C4G2 C 0.4723(3) 0.1918(3) 0.2976(4) 0.0835(13) Uani 1 1 d . . . H4G2 H 0.4077 0.1960 0.2889 0.100 Uiso 1 1 calc R . . C5G2 C 0.5065(3) 0.2150(2) 0.3740(4) 0.0912(14) Uani 1 1 d D . . H5G2 H 0.4683 0.2368 0.4206 0.109 Uiso 1 1 calc R . . C6G2 C 0.5965(2) 0.20834(17) 0.3878(2) 0.0542(8) Uani 1 1 d D . . C7G2 C 0.6839(3) 0.1236(2) 0.1746(3) 0.0468(10) Uani 0.70 1 d P . . C8G2 C 0.5993(8) 0.2410(6) 0.4719(6) 0.062(3) Uani 0.30 1 d PD . . O1X O 0.32119(12) 0.07690(10) 0.14870(11) 0.0352(4) Uani 1 1 d D . . H1OX H 0.2611(17) 0.098(2) 0.168(2) 0.094(12) Uiso 1 1 d D . . C1X C 0.24512(19) -0.10028(15) 0.07270(16) 0.0368(6) Uani 1 1 d . . . H1X H 0.2939 -0.1195 0.1114 0.044 Uiso 1 1 calc R . . C2X C 0.1724(2) -0.15444(16) 0.05132(18) 0.0418(7) Uani 1 1 d . . . H2X H 0.1710 -0.2107 0.0761 0.050 Uiso 1 1 calc R . . C3X C 0.1019(2) -0.12686(16) -0.00604(18) 0.0422(7) Uani 1 1 d . . . H3X H 0.0529 -0.1648 -0.0208 0.051 Uiso 1 1 calc R . . C4X C 0.10173(19) -0.04491(16) -0.04212(17) 0.0385(6) Uani 1 1 d . . . H4X H 0.0531 -0.0263 -0.0812 0.046 Uiso 1 1 calc R . . C5X C 0.13843(18) 0.15744(15) -0.09575(16) 0.0355(6) Uani 1 1 d . . . H5X H 0.0824 0.1400 -0.1242 0.043 Uiso 1 1 calc R . . C6X C 0.16924(19) 0.24090(16) -0.10407(16) 0.0374(6) Uani 1 1 d . . . H6X H 0.1344 0.2808 -0.1392 0.045 Uiso 1 1 calc R . . C7X C 0.25025(19) 0.26713(15) -0.06185(16) 0.0375(6) Uani 1 1 d . . . H7X H 0.2701 0.3248 -0.0680 0.045 Uiso 1 1 calc R . . C8X C 0.30263(18) 0.20969(15) -0.01057(16) 0.0338(6) Uani 1 1 d . . . H8X H 0.3579 0.2278 0.0187 0.041 Uiso 1 1 calc R . . C9X C 0.31528(17) 0.05393(15) 0.05416(15) 0.0303(6) Uani 1 1 d . . . C10X C 0.41174(16) 0.02778(14) 0.02564(15) 0.0293(6) Uani 1 1 d . . . C11X C 0.46857(17) -0.01619(15) 0.08647(16) 0.0326(6) Uani 1 1 d . . . H11X H 0.4481 -0.0274 0.1466 0.039 Uiso 1 1 calc R . . C12X C 0.44496(17) 0.04412(15) -0.06085(16) 0.0323(6) Uani 1 1 d . . . H12X H 0.4079 0.0750 -0.1035 0.039 Uiso 1 1 calc R . . O1Y O 0.82836(12) 0.13137(10) 0.38447(11) 0.0319(4) Uani 1 1 d D . . H1OY H 0.7700(14) 0.1512(16) 0.3647(17) 0.050(8) Uiso 1 1 d D . . C1Y C 0.78577(18) 0.14340(16) 0.59508(16) 0.0370(6) Uani 1 1 d . . . H1Y H 0.8393 0.1776 0.5898 0.044 Uiso 1 1 calc R . . C2Y C 0.7274(2) 0.15355(18) 0.66914(18) 0.0462(7) Uani 1 1 d . . . H2Y H 0.7409 0.1956 0.7144 0.055 Uiso 1 1 calc R . . C3Y C 0.6504(2) 0.1031(2) 0.67689(19) 0.0505(8) Uani 1 1 d . . . H3Y H 0.6117 0.1104 0.7279 0.061 Uiso 1 1 calc R . . C4Y C 0.62864(19) 0.04187(19) 0.61170(19) 0.0471(7) Uani 1 1 d . . . H4Y H 0.5756 0.0071 0.6180 0.056 Uiso 1 1 calc R . . C5Y C 0.61084(19) -0.07999(17) 0.4268(2) 0.0462(7) Uani 1 1 d . . . H5Y H 0.5583 -0.0896 0.4630 0.055 Uiso 1 1 calc R . . C6Y C 0.6206(2) -0.12232(17) 0.3451(2) 0.0524(8) Uani 1 1 d . . . H6Y H 0.5745 -0.1615 0.3252 0.063 Uiso 1 1 calc R . . C7Y C 0.6960(2) -0.10877(16) 0.2916(2) 0.0468(7) Uani 1 1 d . . . H7Y H 0.7015 -0.1388 0.2355 0.056 Uiso 1 1 calc R . . C8Y C 0.76447(18) -0.05141(15) 0.31894(17) 0.0383(6) Uani 1 1 d . . . H8Y H 0.8165 -0.0419 0.2820 0.046 Uiso 1 1 calc R . . C9Y C 0.81688(17) 0.05961(14) 0.44379(15) 0.0295(6) Uani 1 1 d . . . C10Y C 0.91252(16) 0.02771(14) 0.47024(14) 0.0276(6) Uani 1 1 d . . . C11Y C 0.98613(16) 0.08473(15) 0.47500(15) 0.0291(6) Uani 1 1 d . . . H11Y H 0.9775 0.1429 0.4577 0.035 Uiso 1 1 calc R . . C12Y C 0.92791(17) -0.05688(14) 0.49508(15) 0.0295(6) Uani 1 1 d . . . H12Y H 0.8787 -0.0967 0.4916 0.035 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 C1AX 0.0243(14) 0.0314(13) 0.0336(12) -0.0008(10) 0.0001(11) 0.0022(11) C4AX 0.0271(15) 0.0318(13) 0.0333(13) -0.0020(10) -0.0006(11) 0.0011(11) C5AX 0.0263(14) 0.0308(13) 0.0333(12) -0.0027(10) -0.0017(11) 0.0026(11) C8AX 0.0250(14) 0.0318(14) 0.0321(12) -0.0038(10) -0.0007(11) 0.0033(11) C1AY 0.0216(14) 0.0286(13) 0.0377(13) 0.0057(11) -0.0016(11) 0.0064(11) C4AY 0.0240(15) 0.0367(14) 0.0453(15) 0.0141(12) -0.0024(12) 0.0067(12) C5AY 0.0238(15) 0.0276(13) 0.0520(15) 0.0107(12) -0.0093(12) 0.0014(11) C8AY 0.0219(14) 0.0276(13) 0.0450(14) 0.0056(11) -0.0101(11) 0.0041(11) N1G1 0.0276(13) 0.0363(12) 0.0390(11) -0.0018(9) 0.0001(10) 0.0003(10) C2G1 0.0326(16) 0.0382(14) 0.0298(12) -0.0016(11) -0.0033(11) -0.0024(12) C3G1 0.0279(16) 0.0508(17) 0.0351(14) -0.0007(12) -0.0026(12) -0.0044(13) C4G1 0.0306(16) 0.0542(17) 0.0357(13) 0.0000(12) -0.0026(12) 0.0107(13) C5G1 0.0436(18) 0.0426(15) 0.0382(14) 0.0010(12) -0.0028(13) 0.0071(13) C6G1 0.0364(17) 0.0409(16) 0.0378(14) -0.0010(11) 0.0042(12) -0.0029(13) C7G1 0.054(2) 0.0415(16) 0.0532(16) 0.0023(13) 0.0041(15) 0.0006(14) N1G2 0.0278(13) 0.0353(12) 0.0432(12) 0.0025(9) -0.0061(10) 0.0013(10) C2G2 0.070(2) 0.0293(14) 0.0546(18) 0.0069(13) -0.0019(17) -0.0048(15) C3G2 0.107(4) 0.0443(19) 0.079(2) 0.0184(18) -0.061(3) -0.035(2) C4G2 0.053(3) 0.074(3) 0.123(4) 0.026(3) 0.000(3) 0.011(2) C5G2 0.067(3) 0.066(3) 0.142(4) 0.015(3) 0.039(3) 0.014(2) C6G2 0.050(2) 0.0424(16) 0.071(2) 0.0081(15) 0.0231(17) 0.0032(15) C7G2 0.049(3) 0.044(2) 0.047(2) -0.0102(18) 0.004(2) 0.006(2) C8G2 0.093(9) 0.050(6) 0.042(5) 0.017(5) -0.019(6) -0.017(6) O1X 0.0273(11) 0.0415(10) 0.0365(9) -0.0051(7) -0.0049(8) 0.0045(8) C1X 0.0364(17) 0.0328(14) 0.0410(14) 0.0020(11) -0.0025(12) 0.0050(12) C2X 0.0461(19) 0.0301(14) 0.0491(16) -0.0019(12) 0.0020(14) -0.0006(13) C3X 0.0361(17) 0.0386(16) 0.0519(16) -0.0068(12) 0.0002(14) -0.0091(13) C4X 0.0315(16) 0.0383(15) 0.0454(15) -0.0055(12) -0.0036(12) -0.0014(12) C5X 0.0288(15) 0.0384(15) 0.0390(14) -0.0007(11) -0.0083(12) 0.0043(12) C6X 0.0401(18) 0.0353(14) 0.0365(13) 0.0029(11) -0.0035(12) 0.0099(13) C7X 0.0396(18) 0.0286(13) 0.0443(14) -0.0001(11) 0.0024(13) 0.0020(12) C8X 0.0255(15) 0.0316(14) 0.0442(14) -0.0030(11) -0.0014(12) 0.0001(11) C9X 0.0256(15) 0.0326(13) 0.0325(13) -0.0030(10) -0.0023(11) 0.0021(11) C10X 0.0216(14) 0.0275(12) 0.0387(13) -0.0043(10) -0.0048(11) 0.0000(11) C11X 0.0267(15) 0.0371(14) 0.0340(13) -0.0002(11) -0.0015(11) 0.0035(11) C12X 0.0279(15) 0.0322(13) 0.0365(13) 0.0026(10) -0.0083(11) 0.0036(11) O1Y 0.0234(10) 0.0318(9) 0.0404(9) 0.0078(7) -0.0044(8) 0.0021(8) C1Y 0.0327(16) 0.0368(14) 0.0416(14) 0.0033(12) 0.0004(12) 0.0059(12) C2Y 0.047(2) 0.0489(17) 0.0427(15) 0.0014(13) 0.0010(14) 0.0171(15) C3Y 0.0419(19) 0.0649(19) 0.0450(16) 0.0119(15) 0.0115(14) 0.0164(16) C4Y 0.0250(16) 0.0577(18) 0.0586(18) 0.0201(15) 0.0043(14) 0.0060(13) C5Y 0.0290(17) 0.0405(16) 0.0687(19) 0.0179(14) -0.0155(14) -0.0055(13) C6Y 0.0350(19) 0.0375(16) 0.084(2) 0.0025(15) -0.0280(17) -0.0078(13) C7Y 0.0428(19) 0.0381(15) 0.0586(17) -0.0063(13) -0.0252(15) 0.0066(14) C8Y 0.0303(16) 0.0350(14) 0.0493(16) -0.0043(12) -0.0130(13) 0.0043(12) C9Y 0.0223(14) 0.0271(13) 0.0389(13) 0.0032(10) -0.0058(11) 0.0010(10) C10Y 0.0209(14) 0.0299(13) 0.0319(12) -0.0025(10) -0.0030(10) 0.0008(11) C11Y 0.0246(14) 0.0257(12) 0.0368(13) 0.0014(10) -0.0039(11) 0.0016(11) C12Y 0.0221(14) 0.0271(13) 0.0392(13) -0.0012(10) -0.0019(11) -0.0034(11) _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 C1AX C1X 1.382(3) . ? C1AX C4AX 1.402(3) . ? C1AX C9X 1.528(3) . ? C4AX C4X 1.386(3) . ? C4AX C5AX 1.472(3) . ? C5AX C5X 1.391(3) . ? C5AX C8AX 1.402(3) . ? C8AX C8X 1.376(3) . ? C8AX C9X 1.526(3) . ? C1AY C1Y 1.380(3) . ? C1AY C4AY 1.398(3) . ? C1AY C9Y 1.529(3) . ? C4AY C4Y 1.390(3) . ? C4AY C5AY 1.464(4) . ? C5AY C5Y 1.388(4) . ? C5AY C8AY 1.405(3) . ? C8AY C8Y 1.380(3) . ? C8AY C9Y 1.526(3) . ? N1G1 C6G1 1.331(3) . ? N1G1 C2G1 1.348(3) . ? C2G1 C3G1 1.385(4) . ? C2G1 C7G1 1.504(4) . ? C3G1 C4G1 1.373(4) . ? C3G1 H3G1 0.9500 . ? C4G1 C5G1 1.379(4) . ? C4G1 H4G1 0.9500 . ? C5G1 C6G1 1.384(4) . ? C5G1 H5G1 0.9500 . ? C6G1 H6G1 0.9500 . ? C7G1 H7G1 0.9800 . ? C7G1 H7G2 0.9800 . ? C7G1 H7G3 0.9800 . ? N1G2 C6G2 1.318(3) . ? N1G2 C2G2 1.339(4) . ? C2G2 C7G2 1.450(5) . ? C2G2 C3G2 1.503(5) . ? C3G2 C4G2 1.353(6) . ? C3G2 H3G2 0.9500 . ? C4G2 C5G2 1.270(6) . ? C4G2 H4G2 0.9500 . ? C5G2 C6G2 1.328(6) . ? C5G2 H5G2 0.9500 . ? C6G2 C8G2 1.332(9) . ? O1X C9X 1.430(3) . ? O1X H1OX 0.980(19) . ? C1X C2X 1.387(4) . ? C1X H1X 0.9500 . ? C2X C3X 1.385(4) . ? C2X H2X 0.9500 . ? C3X C4X 1.383(4) . ? C3X H3X 0.9500 . ? C4X H4X 0.9500 . ? C5X C6X 1.383(4) . ? C5X H5X 0.9500 . ? C6X C7X 1.386(4) . ? C6X H6X 0.9500 . ? C7X C8X 1.389(3) . ? C7X H7X 0.9500 . ? C8X H8X 0.9500 . ? C9X C10X 1.528(3) . ? C10X C12X 1.386(3) . ? C10X C11X 1.388(3) . ? C11X C12X 1.391(3) 3_655 ? C11X H11X 0.9500 . ? C12X C11X 1.391(3) 3_655 ? C12X H12X 0.9500 . ? O1Y C9Y 1.428(3) . ? O1Y H1OY 0.946(18) . ? C1Y C2Y 1.398(3) . ? C1Y H1Y 0.9500 . ? C2Y C3Y 1.376(4) . ? C2Y H2Y 0.9500 . ? C3Y C4Y 1.383(4) . ? C3Y H3Y 0.9500 . ? C4Y H4Y 0.9500 . ? C5Y C6Y 1.376(4) . ? C5Y H5Y 0.9500 . ? C6Y C7Y 1.376(4) . ? C6Y H6Y 0.9500 . ? C7Y C8Y 1.394(4) . ? C7Y H7Y 0.9500 . ? C8Y H8Y 0.9500 . ? C9Y C10Y 1.524(3) . ? C10Y C12Y 1.386(3) . ? C10Y C11Y 1.394(3) . ? C11Y C12Y 1.390(3) 3_756 ? C11Y H11Y 0.9500 . ? C12Y C11Y 1.390(3) 3_756 ? C12Y H12Y 0.9500 . ? 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 C1X C1AX C4AX 119.9(2) . . ? C1X C1AX C9X 129.2(2) . . ? C4AX C1AX C9X 110.92(19) . . ? C4X C4AX C1AX 120.7(2) . . ? C4X C4AX C5AX 131.0(2) . . ? C1AX C4AX C5AX 108.3(2) . . ? C5X C5AX C8AX 120.1(2) . . ? C5X C5AX C4AX 131.1(2) . . ? C8AX C5AX C4AX 108.7(2) . . ? C8X C8AX C5AX 120.7(2) . . ? C8X C8AX C9X 128.3(2) . . ? C5AX C8AX C9X 110.8(2) . . ? C1Y C1AY C4AY 121.2(2) . . ? C1Y C1AY C9Y 128.1(2) . . ? C4AY C1AY C9Y 110.7(2) . . ? C4Y C4AY C1AY 119.5(2) . . ? C4Y C4AY C5AY 132.0(2) . . ? C1AY C4AY C5AY 108.5(2) . . ? C5Y C5AY C8AY 119.4(2) . . ? C5Y C5AY C4AY 131.5(2) . . ? C8AY C5AY C4AY 109.1(2) . . ? C8Y C8AY C5AY 120.9(2) . . ? C8Y C8AY C9Y 128.9(2) . . ? C5AY C8AY C9Y 110.2(2) . . ? C6G1 N1G1 C2G1 118.1(2) . . ? N1G1 C2G1 C3G1 121.2(2) . . ? N1G1 C2G1 C7G1 116.4(2) . . ? C3G1 C2G1 C7G1 122.4(2) . . ? C4G1 C3G1 C2G1 120.3(2) . . ? C4G1 C3G1 H3G1 119.8 . . ? C2G1 C3G1 H3G1 119.8 . . ? C3G1 C4G1 C5G1 118.4(2) . . ? C3G1 C4G1 H4G1 120.8 . . ? C5G1 C4G1 H4G1 120.8 . . ? C4G1 C5G1 C6G1 118.5(2) . . ? C4G1 C5G1 H5G1 120.8 . . ? C6G1 C5G1 H5G1 120.8 . . ? N1G1 C6G1 C5G1 123.4(2) . . ? N1G1 C6G1 H6G1 118.3 . . ? C5G1 C6G1 H6G1 118.3 . . ? C2G1 C7G1 H7G1 109.5 . . ? C2G1 C7G1 H7G2 109.5 . . ? H7G1 C7G1 H7G2 109.5 . . ? C2G1 C7G1 H7G3 109.5 . . ? H7G1 C7G1 H7G3 109.5 . . ? H7G2 C7G1 H7G3 109.5 . . ? C6G2 N1G2 C2G2 118.5(3) . . ? N1G2 C2G2 C7G2 122.9(3) . . ? N1G2 C2G2 C3G2 117.2(3) . . ? C7G2 C2G2 C3G2 119.9(3) . . ? C4G2 C3G2 C2G2 116.1(3) . . ? C4G2 C3G2 H3G2 122.0 . . ? C2G2 C3G2 H3G2 122.0 . . ? C5G2 C4G2 C3G2 123.6(4) . . ? C5G2 C4G2 H4G2 118.2 . . ? C3G2 C4G2 H4G2 118.2 . . ? C4G2 C5G2 C6G2 119.0(4) . . ? C4G2 C5G2 H5G2 120.5 . . ? C6G2 C5G2 H5G2 120.5 . . ? N1G2 C6G2 C5G2 125.6(4) . . ? N1G2 C6G2 C8G2 137.1(6) . . ? C5G2 C6G2 C8G2 97.3(6) . . ? C9X O1X H1OX 109(2) . . ? C1AX C1X C2X 119.5(3) . . ? C1AX C1X H1X 120.3 . . ? C2X C1X H1X 120.3 . . ? C3X C2X C1X 120.3(2) . . ? C3X C2X H2X 119.9 . . ? C1X C2X H2X 119.9 . . ? C4X C3X C2X 121.0(3) . . ? C4X C3X H3X 119.5 . . ? C2X C3X H3X 119.5 . . ? C3X C4X C4AX 118.7(3) . . ? C3X C4X H4X 120.7 . . ? C4AX C4X H4X 120.7 . . ? C6X C5X C5AX 118.8(2) . . ? C6X C5X H5X 120.6 . . ? C5AX C5X H5X 120.6 . . ? C5X C6X C7X 120.9(2) . . ? C5X C6X H6X 119.5 . . ? C7X C6X H6X 119.5 . . ? C6X C7X C8X 120.5(2) . . ? C6X C7X H7X 119.7 . . ? C8X C7X H7X 119.7 . . ? C8AX C8X C7X 119.0(2) . . ? C8AX C8X H8X 120.5 . . ? C7X C8X H8X 120.5 . . ? O1X C9X C8AX 111.22(18) . . ? O1X C9X C1AX 111.73(18) . . ? C8AX C9X C1AX 101.32(19) . . ? O1X C9X C10X 106.82(19) . . ? C8AX C9X C10X 114.29(19) . . ? C1AX C9X C10X 111.56(18) . . ? C12X C10X C11X 117.6(2) . . ? C12X C10X C9X 122.5(2) . . ? C11X C10X C9X 119.9(2) . . ? C10X C11X C12X 121.1(2) . 3_655 ? C10X C11X H11X 119.5 . . ? C12X C11X H11X 119.5 3_655 . ? C10X C12X C11X 121.3(2) . 3_655 ? C10X C12X H12X 119.3 . . ? C11X C12X H12X 119.3 3_655 . ? C9Y O1Y H1OY 109.2(16) . . ? C1AY C1Y C2Y 118.6(3) . . ? C1AY C1Y H1Y 120.7 . . ? C2Y C1Y H1Y 120.7 . . ? C3Y C2Y C1Y 120.4(3) . . ? C3Y C2Y H2Y 119.8 . . ? C1Y C2Y H2Y 119.8 . . ? C2Y C3Y C4Y 121.1(2) . . ? C2Y C3Y H3Y 119.5 . . ? C4Y C3Y H3Y 119.5 . . ? C3Y C4Y C4AY 119.2(3) . . ? C3Y C4Y H4Y 120.4 . . ? C4AY C4Y H4Y 120.4 . . ? C6Y C5Y C5AY 119.5(3) . . ? C6Y C5Y H5Y 120.3 . . ? C5AY C5Y H5Y 120.3 . . ? C7Y C6Y C5Y 121.0(3) . . ? C7Y C6Y H6Y 119.5 . . ? C5Y C6Y H6Y 119.5 . . ? C6Y C7Y C8Y 120.7(3) . . ? C6Y C7Y H7Y 119.7 . . ? C8Y C7Y H7Y 119.7 . . ? C8AY C8Y C7Y 118.5(2) . . ? C8AY C8Y H8Y 120.7 . . ? C7Y C8Y H8Y 120.7 . . ? O1Y C9Y C10Y 107.14(18) . . ? O1Y C9Y C8AY 111.80(19) . . ? C10Y C9Y C8AY 114.16(18) . . ? O1Y C9Y C1AY 112.49(17) . . ? C10Y C9Y C1AY 109.80(18) . . ? C8AY C9Y C1AY 101.51(19) . . ? C12Y C10Y C11Y 118.2(2) . . ? C12Y C10Y C9Y 121.4(2) . . ? C11Y C10Y C9Y 120.3(2) . . ? C12Y C11Y C10Y 120.4(2) 3_756 . ? C12Y C11Y H11Y 119.8 3_756 . ? C10Y C11Y H11Y 119.8 . . ? C10Y C12Y C11Y 121.4(2) . 3_756 ? C10Y C12Y H12Y 119.3 . . ? C11Y C12Y H12Y 119.3 3_756 . ? 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 C1X C1AX C4AX C4X -0.3(3) . . . . ? C9X C1AX C4AX C4X -177.9(2) . . . . ? C1X C1AX C4AX C5AX 178.1(2) . . . . ? C9X C1AX C4AX C5AX 0.5(2) . . . . ? C4X C4AX C5AX C5X 2.1(4) . . . . ? C1AX C4AX C5AX C5X -176.1(2) . . . . ? C4X C4AX C5AX C8AX 178.3(2) . . . . ? C1AX C4AX C5AX C8AX 0.1(2) . . . . ? C5X C5AX C8AX C8X 0.5(3) . . . . ? C4AX C5AX C8AX C8X -176.2(2) . . . . ? C5X C5AX C8AX C9X 176.0(2) . . . . ? C4AX C5AX C8AX C9X -0.7(2) . . . . ? C1Y C1AY C4AY C4Y -1.1(3) . . . . ? C9Y C1AY C4AY C4Y 178.7(2) . . . . ? C1Y C1AY C4AY C5AY 177.4(2) . . . . ? C9Y C1AY C4AY C5AY -2.8(3) . . . . ? C4Y C4AY C5AY C5Y 3.5(4) . . . . ? C1AY C4AY C5AY C5Y -174.7(3) . . . . ? C4Y C4AY C5AY C8AY -179.6(2) . . . . ? C1AY C4AY C5AY C8AY 2.2(3) . . . . ? C5Y C5AY C8AY C8Y -1.2(3) . . . . ? C4AY C5AY C8AY C8Y -178.6(2) . . . . ? C5Y C5AY C8AY C9Y 176.7(2) . . . . ? C4AY C5AY C8AY C9Y -0.8(3) . . . . ? C6G1 N1G1 C2G1 C3G1 -0.3(3) . . . . ? C6G1 N1G1 C2G1 C7G1 179.7(2) . . . . ? N1G1 C2G1 C3G1 C4G1 -0.7(4) . . . . ? C7G1 C2G1 C3G1 C4G1 179.4(2) . . . . ? C2G1 C3G1 C4G1 C5G1 1.1(4) . . . . ? C3G1 C4G1 C5G1 C6G1 -0.6(4) . . . . ? C2G1 N1G1 C6G1 C5G1 0.8(4) . . . . ? C4G1 C5G1 C6G1 N1G1 -0.3(4) . . . . ? C6G2 N1G2 C2G2 C7G2 178.9(3) . . . . ? C6G2 N1G2 C2G2 C3G2 -0.2(3) . . . . ? N1G2 C2G2 C3G2 C4G2 -0.4(4) . . . . ? C7G2 C2G2 C3G2 C4G2 -179.5(3) . . . . ? C2G2 C3G2 C4G2 C5G2 1.0(5) . . . . ? C3G2 C4G2 C5G2 C6G2 -1.0(6) . . . . ? C2G2 N1G2 C6G2 C5G2 0.2(4) . . . . ? C2G2 N1G2 C6G2 C8G2 -176.9(6) . . . . ? C4G2 C5G2 C6G2 N1G2 0.4(6) . . . . ? C4G2 C5G2 C6G2 C8G2 178.4(5) . . . . ? C4AX C1AX C1X C2X -0.3(3) . . . . ? C9X C1AX C1X C2X 176.8(2) . . . . ? C1AX C1X C2X C3X 0.9(4) . . . . ? C1X C2X C3X C4X -0.9(4) . . . . ? C2X C3X C4X C4AX 0.3(4) . . . . ? C1AX C4AX C4X C3X 0.3(3) . . . . ? C5AX C4AX C4X C3X -177.7(2) . . . . ? C8AX C5AX C5X C6X 0.4(3) . . . . ? C4AX C5AX C5X C6X 176.2(2) . . . . ? C5AX C5X C6X C7X -0.8(3) . . . . ? C5X C6X C7X C8X 0.4(3) . . . . ? C5AX C8AX C8X C7X -0.9(3) . . . . ? C9X C8AX C8X C7X -175.6(2) . . . . ? C6X C7X C8X C8AX 0.5(3) . . . . ? C8X C8AX C9X O1X 57.1(3) . . . . ? C5AX C8AX C9X O1X -118.0(2) . . . . ? C8X C8AX C9X C1AX 176.0(2) . . . . ? C5AX C8AX C9X C1AX 0.9(2) . . . . ? C8X C8AX C9X C10X -63.9(3) . . . . ? C5AX C8AX C9X C10X 121.0(2) . . . . ? C1X C1AX C9X O1X -59.7(3) . . . . ? C4AX C1AX C9X O1X 117.7(2) . . . . ? C1X C1AX C9X C8AX -178.2(2) . . . . ? C4AX C1AX C9X C8AX -0.8(2) . . . . ? C1X C1AX C9X C10X 59.8(3) . . . . ? C4AX C1AX C9X C10X -122.8(2) . . . . ? O1X C9X C10X C12X -145.5(2) . . . . ? C8AX C9X C10X C12X -22.0(3) . . . . ? C1AX C9X C10X C12X 92.2(3) . . . . ? O1X C9X C10X C11X 36.4(3) . . . . ? C8AX C9X C10X C11X 159.9(2) . . . . ? C1AX C9X C10X C11X -85.9(3) . . . . ? C12X C10X C11X C12X -1.1(4) . . . 3_655 ? C9X C10X C11X C12X 177.1(2) . . . 3_655 ? C11X C10X C12X C11X 1.1(4) . . . 3_655 ? C9X C10X C12X C11X -177.0(2) . . . 3_655 ? C4AY C1AY C1Y C2Y 0.1(4) . . . . ? C9Y C1AY C1Y C2Y -179.7(2) . . . . ? C1AY C1Y C2Y C3Y 0.7(4) . . . . ? C1Y C2Y C3Y C4Y -0.5(4) . . . . ? C2Y C3Y C4Y C4AY -0.5(4) . . . . ? C1AY C4AY C4Y C3Y 1.3(4) . . . . ? C5AY C4AY C4Y C3Y -176.8(2) . . . . ? C8AY C5AY C5Y C6Y 1.1(4) . . . . ? C4AY C5AY C5Y C6Y 177.8(2) . . . . ? C5AY C5Y C6Y C7Y -0.4(4) . . . . ? C5Y C6Y C7Y C8Y -0.2(4) . . . . ? C5AY C8AY C8Y C7Y 0.5(3) . . . . ? C9Y C8AY C8Y C7Y -176.8(2) . . . . ? C6Y C7Y C8Y C8AY 0.1(4) . . . . ? C8Y C8AY C9Y O1Y 56.6(3) . . . . ? C5AY C8AY C9Y O1Y -121.0(2) . . . . ? C8Y C8AY C9Y C10Y -65.2(3) . . . . ? C5AY C8AY C9Y C10Y 117.2(2) . . . . ? C8Y C8AY C9Y C1AY 176.7(2) . . . . ? C5AY C8AY C9Y C1AY -0.8(2) . . . . ? C1Y C1AY C9Y O1Y -58.3(3) . . . . ? C4AY C1AY C9Y O1Y 121.9(2) . . . . ? C1Y C1AY C9Y C10Y 60.9(3) . . . . ? C4AY C1AY C9Y C10Y -118.9(2) . . . . ? C1Y C1AY C9Y C8AY -178.0(2) . . . . ? C4AY C1AY C9Y C8AY 2.3(2) . . . . ? O1Y C9Y C10Y C12Y -153.83(19) . . . . ? C8AY C9Y C10Y C12Y -29.5(3) . . . . ? C1AY C9Y C10Y C12Y 83.7(3) . . . . ? O1Y C9Y C10Y C11Y 29.9(3) . . . . ? C8AY C9Y C10Y C11Y 154.2(2) . . . . ? C1AY C9Y C10Y C11Y -92.6(2) . . . . ? C12Y C10Y C11Y C12Y -0.7(3) . . . 3_756 ? C9Y C10Y C11Y C12Y 175.7(2) . . . 3_756 ? C11Y C10Y C12Y C11Y 0.7(4) . . . 3_756 ? C9Y C10Y C12Y C11Y -175.7(2) . . . 3_756 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1X H1OX N1G1 0.980(19) 1.85(2) 2.818(3) 170(3) . O1Y H1OY N1G2 0.946(18) 1.798(19) 2.741(3) 175(2) . _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.65 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.553 _refine_diff_density_min -0.285 _refine_diff_density_rms 0.060 # Attachment '- H3PIC.CIF' data_h3pic _database_code_depnum_ccdc_archive 'CCDC 817291' #TrackingRef '- H3PIC.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1,4-bis(9-hydroxyfluoren-9-yl)benzene. 3-picoline clathrate' ; _chemical_name_common "'1,4-bis(9-hydroxyfluoren-9-yl)benzene. 3-picoline clathrate'" _chemical_melting_point 264-265 _chemical_formula_moiety 'C32 H22 O2, 2(C6 H7 N)' _chemical_formula_sum 'C44 H36 N2 O2' _chemical_formula_weight 624.75 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 triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.4854(2) _cell_length_b 13.3617(3) _cell_length_c 14.0639(4) _cell_angle_alpha 82.2870(10) _cell_angle_beta 81.0670(10) _cell_angle_gamma 72.2300(10) _cell_volume 1669.69(7) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3704 _cell_measurement_theta_min 2.1 _cell_measurement_theta_max 25.3 _exptl_crystal_description 'clear blocks' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.243 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 660 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type none _exptl_special_details ; Distances of O1-H1O and O2-H2O are restrainted to 0.97(2) angstroms. ; _diffrn_ambient_temperature 173(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 Kappa CCD' _diffrn_measurement_method 'Combination of phi and omega' _diffrn_reflns_number 11272 _diffrn_reflns_av_R_equivalents 0.0347 _diffrn_reflns_av_sigmaI/netI 0.0685 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 25.29 _reflns_number_total 6022 _reflns_number_gt 3704 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 2000)' _computing_cell_refinement 'Collect (Nonius, 2000)' _computing_data_reduction 'Collect (Nonius, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSEED, graphical interface to SHELX (1999)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0520P)^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 none _refine_ls_number_reflns 6022 _refine_ls_number_parameters 443 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0850 _refine_ls_R_factor_gt 0.0422 _refine_ls_wR_factor_ref 0.1070 _refine_ls_wR_factor_gt 0.0913 _refine_ls_goodness_of_fit_ref 0.932 _refine_ls_restrained_S_all 0.932 _refine_ls_shift/su_max 0.001 _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 0.29761(13) 0.68191(9) 0.98884(8) 0.0233(3) Uani 1 1 d D . . H1O H 0.219(2) 0.7107(18) 0.9515(16) 0.099(9) Uiso 1 1 d D . . O2 O 0.71933(12) 0.80104(9) 0.53121(8) 0.0243(3) Uani 1 1 d D . . H2O H 0.762(2) 0.8043(16) 0.4639(11) 0.073(7) Uiso 1 1 d D . . C1 C 0.23282(18) 0.93204(13) 0.97869(12) 0.0238(4) Uani 1 1 d . . . H1 H 0.1722 0.9278 0.9325 0.029 Uiso 1 1 calc R . . C2 C 0.20211(19) 1.02393(13) 1.02456(12) 0.0267(4) Uani 1 1 d . . . H2 H 0.1207 1.0831 1.0090 0.032 Uiso 1 1 calc R . . C3 C 0.2901(2) 1.02934(14) 1.09305(12) 0.0291(4) Uani 1 1 d . . . H3 H 0.2680 1.0922 1.1241 0.035 Uiso 1 1 calc R . . C4 C 0.4095(2) 0.94423(13) 1.11641(12) 0.0274(4) Uani 1 1 d . . . H4 H 0.4686 0.9481 1.1637 0.033 Uiso 1 1 calc R . . C5 C 0.6717(2) 0.71728(14) 1.13954(12) 0.0292(4) Uani 1 1 d . . . H5 H 0.6856 0.7631 1.1811 0.035 Uiso 1 1 calc R . . C6 C 0.7638(2) 0.61481(14) 1.13646(13) 0.0323(5) Uani 1 1 d . . . H6 H 0.8419 0.5904 1.1763 0.039 Uiso 1 1 calc R . . C7 C 0.74437(19) 0.54695(14) 1.07628(12) 0.0291(4) Uani 1 1 d . . . H7 H 0.8085 0.4767 1.0758 0.035 Uiso 1 1 calc R . . C8 C 0.63110(18) 0.58152(13) 1.01657(12) 0.0237(4) Uani 1 1 d . . . H8 H 0.6178 0.5356 0.9749 0.028 Uiso 1 1 calc R . . C9 C 0.40629(17) 0.73890(12) 0.96253(11) 0.0193(4) Uani 1 1 d . . . C10 C 0.45378(17) 0.74321(12) 0.85356(11) 0.0188(4) Uani 1 1 d . . . C11 C 0.46827(17) 0.65699(12) 0.80289(11) 0.0212(4) Uani 1 1 d . . . H11 H 0.4458 0.5960 0.8364 0.025 Uiso 1 1 calc R . . C12 C 0.48707(17) 0.83099(12) 0.80169(11) 0.0210(4) Uani 1 1 d . . . H12 H 0.4772 0.8910 0.8344 0.025 Uiso 1 1 calc R . . C1' C 0.77131(19) 0.55726(13) 0.52553(12) 0.0253(4) Uani 1 1 d . . . H1' H 0.8280 0.5575 0.5755 0.030 Uiso 1 1 calc R . . C2' C 0.8049(2) 0.46856(14) 0.47422(13) 0.0316(4) Uani 1 1 d . . . H2' H 0.8844 0.4079 0.4895 0.038 Uiso 1 1 calc R . . C3' C 0.7221(2) 0.46907(14) 0.40106(13) 0.0335(5) Uani 1 1 d . . . H3' H 0.7453 0.4084 0.3667 0.040 Uiso 1 1 calc R . . C4' C 0.6064(2) 0.55659(13) 0.37727(12) 0.0300(4) Uani 1 1 d . . . H4' H 0.5512 0.5566 0.3264 0.036 Uiso 1 1 calc R . . C5' C 0.3535(2) 0.78759(14) 0.35420(12) 0.0303(4) Uani 1 1 d . . . H5' H 0.3406 0.7443 0.3099 0.036 Uiso 1 1 calc R . . C6' C 0.2665(2) 0.89197(14) 0.35652(13) 0.0335(5) Uani 1 1 d . . . H6' H 0.1937 0.9203 0.3131 0.040 Uiso 1 1 calc R . . C7' C 0.28447(19) 0.95557(14) 0.42153(12) 0.0289(4) Uani 1 1 d . . . H7' H 0.2247 1.0270 0.4216 0.035 Uiso 1 1 calc R . . C8' C 0.38928(18) 0.91545(13) 0.48639(12) 0.0248(4) Uani 1 1 d . . . H8' H 0.4006 0.9586 0.5314 0.030 Uiso 1 1 calc R . . C9' C 0.60267(17) 0.75103(12) 0.54489(11) 0.0204(4) Uani 1 1 d . . . C10' C 0.54945(17) 0.74667(12) 0.65279(11) 0.0193(4) Uani 1 1 d . . . C11' C 0.53415(18) 0.83295(13) 0.70353(11) 0.0221(4) Uani 1 1 d . . . H11' H 0.5564 0.8940 0.6701 0.027 Uiso 1 1 calc R . . C12' C 0.51493(17) 0.65897(12) 0.70437(11) 0.0216(4) Uani 1 1 d . . . H12' H 0.5235 0.5994 0.6715 0.026 Uiso 1 1 calc R . . C1A C 0.35251(18) 0.84739(12) 1.00137(11) 0.0195(4) Uani 1 1 d . . . C4A C 0.44183(18) 0.85297(13) 1.07000(11) 0.0212(4) Uani 1 1 d . . . C5A C 0.55820(18) 0.75179(13) 1.08042(11) 0.0221(4) Uani 1 1 d . . . C8A C 0.53870(18) 0.68353(13) 1.01901(11) 0.0207(4) Uani 1 1 d . . . C1A' C 0.65512(18) 0.64420(13) 0.50280(11) 0.0210(4) Uani 1 1 d . . . C4A' C 0.57175(18) 0.64450(13) 0.42871(11) 0.0228(4) Uani 1 1 d . . . C5A' C 0.46005(18) 0.74778(13) 0.41796(11) 0.0231(4) Uani 1 1 d . . . C8A' C 0.47695(18) 0.81153(13) 0.48433(11) 0.0208(4) Uani 1 1 d . . . N1G1 N 0.07026(16) 0.75102(11) 0.86658(11) 0.0311(4) Uani 1 1 d . . . C2G1 C 0.10259(19) 0.78784(13) 0.77497(13) 0.0294(4) Uani 1 1 d . . . H2G1 H 0.1814 0.8196 0.7614 0.035 Uiso 1 1 calc R . . C3G1 C 0.02914(18) 0.78297(13) 0.69834(12) 0.0265(4) Uani 1 1 d . . . C4G1 C -0.08443(19) 0.73525(14) 0.71982(13) 0.0301(4) Uani 1 1 d . . . H4G1 H -0.1372 0.7285 0.6700 0.036 Uiso 1 1 calc R . . C5G1 C -0.12052(19) 0.69758(14) 0.81390(13) 0.0303(4) Uani 1 1 d . . . H5G1 H -0.1991 0.6657 0.8294 0.036 Uiso 1 1 calc R . . C6G1 C -0.04167(19) 0.70663(13) 0.88476(13) 0.0298(4) Uani 1 1 d . . . H6G1 H -0.0673 0.6804 0.9492 0.036 Uiso 1 1 calc R . . C7G1 C 0.0745(2) 0.82509(15) 0.59780(13) 0.0382(5) Uani 1 1 d . . . H7GA H 0.0138 0.8119 0.5532 0.057 Uiso 1 1 calc R . . H7GC H 0.1800 0.7897 0.5785 0.057 Uiso 1 1 calc R . . H7GB H 0.0594 0.9012 0.5960 0.057 Uiso 1 1 calc R . . N1G2 N 0.85525(17) 0.80111(13) 0.34448(10) 0.0352(4) Uani 1 1 d . . . C2G2 C 0.9448(2) 0.70739(15) 0.31897(12) 0.0330(5) Uani 1 1 d . . . H2G2 H 0.9324 0.6458 0.3573 0.040 Uiso 1 1 calc R . . C3G2 C 1.0542(2) 0.69458(15) 0.24039(12) 0.0316(5) Uani 1 1 d . . . C4G2 C 1.0696(2) 0.78546(15) 0.18528(13) 0.0341(5) Uani 1 1 d . . . H4G2 H 1.1427 0.7810 0.1303 0.041 Uiso 1 1 calc R . . C5G2 C 0.9780(2) 0.88269(15) 0.21064(13) 0.0354(5) Uani 1 1 d . . . H5G2 H 0.9879 0.9456 0.1735 0.042 Uiso 1 1 calc R . . C6G2 C 0.8727(2) 0.88755(15) 0.29002(13) 0.0352(5) Uani 1 1 d . . . H6G2 H 0.8100 0.9547 0.3069 0.042 Uiso 1 1 calc R . . C7G2 C 1.1523(2) 0.58748(16) 0.21757(15) 0.0526(6) Uani 1 1 d . . . H7GD H 1.2483 0.5742 0.2420 0.079 Uiso 1 1 calc R . . H7GE H 1.1688 0.5840 0.1474 0.079 Uiso 1 1 calc R . . H7GF H 1.1042 0.5340 0.2483 0.079 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 0.0243(7) 0.0237(7) 0.0244(7) -0.0011(5) -0.0008(5) -0.0121(6) O2 0.0247(7) 0.0312(7) 0.0206(7) -0.0041(5) 0.0022(5) -0.0149(6) C1 0.0229(10) 0.0247(10) 0.0224(10) -0.0022(8) -0.0015(8) -0.0055(8) C2 0.0265(10) 0.0216(10) 0.0283(10) -0.0024(8) -0.0004(8) -0.0033(8) C3 0.0354(11) 0.0222(10) 0.0300(11) -0.0084(8) 0.0002(9) -0.0083(9) C4 0.0341(11) 0.0268(11) 0.0238(10) -0.0043(8) -0.0048(8) -0.0112(9) C5 0.0338(11) 0.0276(11) 0.0284(10) -0.0016(8) -0.0106(9) -0.0094(9) C6 0.0313(11) 0.0319(11) 0.0342(11) 0.0029(9) -0.0133(9) -0.0078(10) C7 0.0293(10) 0.0226(10) 0.0326(11) 0.0026(8) -0.0059(9) -0.0047(9) C8 0.0252(10) 0.0205(10) 0.0244(10) -0.0007(8) -0.0019(8) -0.0064(8) C9 0.0204(9) 0.0192(9) 0.0196(9) -0.0012(7) -0.0021(7) -0.0080(8) C10 0.0164(9) 0.0209(9) 0.0193(9) -0.0032(7) -0.0016(7) -0.0056(8) C11 0.0240(9) 0.0182(9) 0.0212(10) 0.0004(7) -0.0010(7) -0.0077(8) C12 0.0215(9) 0.0204(9) 0.0223(10) -0.0059(7) -0.0018(7) -0.0065(8) C1' 0.0248(10) 0.0285(10) 0.0222(10) -0.0020(8) -0.0025(8) -0.0074(9) C2' 0.0307(11) 0.0240(10) 0.0359(11) -0.0046(9) -0.0008(9) -0.0025(9) C3' 0.0413(12) 0.0263(11) 0.0338(12) -0.0106(9) -0.0011(9) -0.0094(10) C4' 0.0356(11) 0.0295(11) 0.0281(11) -0.0062(9) -0.0056(9) -0.0117(10) C5' 0.0349(11) 0.0314(11) 0.0272(10) -0.0026(8) -0.0092(9) -0.0106(10) C6' 0.0326(11) 0.0384(12) 0.0288(11) 0.0049(9) -0.0104(9) -0.0095(10) C7' 0.0265(10) 0.0242(10) 0.0331(11) 0.0026(8) -0.0023(8) -0.0058(9) C8' 0.0246(10) 0.0246(10) 0.0256(10) -0.0021(8) -0.0001(8) -0.0095(9) C9' 0.0205(9) 0.0218(9) 0.0206(9) -0.0015(7) -0.0008(7) -0.0097(8) C10' 0.0171(9) 0.0233(10) 0.0185(9) -0.0022(7) -0.0020(7) -0.0073(8) C11' 0.0258(10) 0.0215(10) 0.0210(10) -0.0004(8) -0.0010(8) -0.0113(8) C12' 0.0225(9) 0.0217(10) 0.0219(10) -0.0058(8) -0.0009(7) -0.0079(8) C1A 0.0217(9) 0.0201(9) 0.0163(9) -0.0010(7) 0.0030(7) -0.0084(8) C4A 0.0252(10) 0.0223(10) 0.0174(9) -0.0013(7) 0.0006(7) -0.0103(8) C5A 0.0260(10) 0.0211(10) 0.0198(9) 0.0006(7) -0.0024(8) -0.0088(8) C8A 0.0236(9) 0.0217(9) 0.0177(9) 0.0018(7) -0.0003(7) -0.0107(8) C1A' 0.0215(9) 0.0224(10) 0.0183(9) -0.0015(7) 0.0027(7) -0.0080(8) C4A' 0.0258(10) 0.0238(10) 0.0199(9) -0.0020(8) -0.0005(8) -0.0099(8) C5A' 0.0244(10) 0.0238(10) 0.0214(10) -0.0011(8) -0.0015(8) -0.0088(8) C8A' 0.0227(9) 0.0233(10) 0.0172(9) 0.0013(7) -0.0005(7) -0.0102(8) N1G1 0.0287(9) 0.0297(9) 0.0352(10) -0.0010(7) -0.0087(7) -0.0074(8) C2G1 0.0244(10) 0.0226(10) 0.0413(12) 0.0006(9) -0.0081(9) -0.0065(9) C3G1 0.0191(9) 0.0243(10) 0.0319(11) -0.0028(8) -0.0025(8) -0.0003(8) C4G1 0.0234(10) 0.0325(11) 0.0355(11) -0.0066(9) -0.0064(8) -0.0070(9) C5G1 0.0216(10) 0.0288(11) 0.0405(12) -0.0048(9) -0.0007(9) -0.0083(9) C6G1 0.0258(10) 0.0249(10) 0.0341(11) -0.0012(8) -0.0015(8) -0.0023(9) C7G1 0.0275(11) 0.0420(12) 0.0390(12) 0.0034(10) -0.0024(9) -0.0050(10) N1G2 0.0349(10) 0.0437(11) 0.0283(9) -0.0062(8) 0.0040(7) -0.0158(9) C2G2 0.0366(11) 0.0381(12) 0.0251(11) 0.0009(9) -0.0008(9) -0.0148(10) C3G2 0.0290(11) 0.0383(12) 0.0233(10) -0.0018(9) -0.0018(8) -0.0049(10) C4G2 0.0265(11) 0.0469(13) 0.0247(11) 0.0025(9) 0.0023(8) -0.0096(10) C5G2 0.0369(12) 0.0391(12) 0.0294(11) 0.0046(9) -0.0026(9) -0.0139(10) C6G2 0.0349(11) 0.0370(12) 0.0330(11) -0.0033(9) -0.0005(9) -0.0110(10) C7G2 0.0516(14) 0.0459(14) 0.0455(14) -0.0001(11) 0.0042(11) 0.0008(12) _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 C9 1.4369(17) . ? O1 H1O 0.932(16) . ? O2 C9' 1.4348(17) . ? O2 H2O 0.971(15) . ? C1 C1A 1.379(2) . ? C1 C2 1.394(2) . ? C1 H1 0.9500 . ? C2 C3 1.391(2) . ? C2 H2 0.9500 . ? C3 C4 1.383(2) . ? C3 H3 0.9500 . ? C4 C4A 1.389(2) . ? C4 H4 0.9500 . ? C5 C6 1.383(2) . ? C5 C5A 1.391(2) . ? C5 H5 0.9500 . ? C6 C7 1.389(2) . ? C6 H6 0.9500 . ? C7 C8 1.395(2) . ? C7 H7 0.9500 . ? C8 C8A 1.379(2) . ? C8 H8 0.9500 . ? C9 C10 1.527(2) . ? C9 C1A 1.528(2) . ? C9 C8A 1.530(2) . ? C10 C12 1.390(2) . ? C10 C11 1.395(2) . ? C11 C12' 1.387(2) . ? C11 H11 0.9500 . ? C12 C11' 1.383(2) . ? C12 H12 0.9500 . ? C1' C1A' 1.376(2) . ? C1' C2' 1.398(2) . ? C1' H1' 0.9500 . ? C2' C3' 1.386(2) . ? C2' H2' 0.9500 . ? C3' C4' 1.382(2) . ? C3' H3' 0.9500 . ? C4' C4A' 1.389(2) . ? C4' H4' 0.9500 . ? C5' C6' 1.389(2) . ? C5' C5A' 1.390(2) . ? C5' H5' 0.9500 . ? C6' C7' 1.390(2) . ? C6' H6' 0.9500 . ? C7' C8' 1.390(2) . ? C7' H7' 0.9500 . ? C8' C8A' 1.385(2) . ? C8' H8' 0.9500 . ? C9' C10' 1.522(2) . ? C9' C1A' 1.529(2) . ? C9' C8A' 1.531(2) . ? C10' C12' 1.392(2) . ? C10' C11' 1.395(2) . ? C11' H11' 0.9500 . ? C12' H12' 0.9500 . ? C1A C4A 1.402(2) . ? C4A C5A 1.468(2) . ? C5A C8A 1.406(2) . ? C1A' C4A' 1.401(2) . ? C4A' C5A' 1.467(2) . ? C5A' C8A' 1.402(2) . ? N1G1 C2G1 1.340(2) . ? N1G1 C6G1 1.343(2) . ? C2G1 C3G1 1.389(2) . ? C2G1 H2G1 0.9500 . ? C3G1 C4G1 1.387(2) . ? C3G1 C7G1 1.499(2) . ? C4G1 C5G1 1.381(2) . ? C4G1 H4G1 0.9500 . ? C5G1 C6G1 1.373(2) . ? C5G1 H5G1 0.9500 . ? C6G1 H6G1 0.9500 . ? C7G1 H7GA 0.9800 . ? C7G1 H7GC 0.9800 . ? C7G1 H7GB 0.9800 . ? N1G2 C6G2 1.337(2) . ? N1G2 C2G2 1.340(2) . ? C2G2 C3G2 1.383(2) . ? C2G2 H2G2 0.9500 . ? C3G2 C4G2 1.385(2) . ? C3G2 C7G2 1.495(3) . ? C4G2 C5G2 1.382(3) . ? C4G2 H4G2 0.9500 . ? C5G2 C6G2 1.372(2) . ? C5G2 H5G2 0.9500 . ? C6G2 H6G2 0.9500 . ? C7G2 H7GD 0.9800 . ? C7G2 H7GE 0.9800 . ? C7G2 H7GF 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 O1 H1O 109.4(15) . . ? C9' O2 H2O 110.9(11) . . ? C1A C1 C2 119.05(15) . . ? C1A C1 H1 120.5 . . ? C2 C1 H1 120.5 . . ? C3 C2 C1 120.29(17) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C4 C3 C2 120.72(16) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 C4A 119.26(16) . . ? C3 C4 H4 120.4 . . ? C4A C4 H4 120.4 . . ? C6 C5 C5A 118.51(15) . . ? C6 C5 H5 120.7 . . ? C5A C5 H5 120.7 . . ? C5 C6 C7 121.36(16) . . ? C5 C6 H6 119.3 . . ? C7 C6 H6 119.3 . . ? C6 C7 C8 120.25(17) . . ? C6 C7 H7 119.9 . . ? C8 C7 H7 119.9 . . ? C8A C8 C7 118.88(15) . . ? C8A C8 H8 120.6 . . ? C7 C8 H8 120.6 . . ? O1 C9 C10 110.47(11) . . ? O1 C9 C1A 111.76(12) . . ? C10 C9 C1A 113.42(12) . . ? O1 C9 C8A 107.73(12) . . ? C10 C9 C8A 111.56(13) . . ? C1A C9 C8A 101.46(12) . . ? C12 C10 C11 117.63(14) . . ? C12 C10 C9 121.89(13) . . ? C11 C10 C9 120.46(13) . . ? C12' C11 C10 120.99(14) . . ? C12' C11 H11 119.5 . . ? C10 C11 H11 119.5 . . ? C11' C12 C10 121.46(14) . . ? C11' C12 H12 119.3 . . ? C10 C12 H12 119.3 . . ? C1A' C1' C2' 119.21(16) . . ? C1A' C1' H1' 120.4 . . ? C2' C1' H1' 120.4 . . ? C3' C2' C1' 120.02(17) . . ? C3' C2' H2' 120.0 . . ? C1' C2' H2' 120.0 . . ? C4' C3' C2' 120.98(16) . . ? C4' C3' H3' 119.5 . . ? C2' C3' H3' 119.5 . . ? C3' C4' C4A' 119.18(16) . . ? C3' C4' H4' 120.4 . . ? C4A' C4' H4' 120.4 . . ? C6' C5' C5A' 118.70(15) . . ? C6' C5' H5' 120.6 . . ? C5A' C5' H5' 120.6 . . ? C5' C6' C7' 120.88(17) . . ? C5' C6' H6' 119.6 . . ? C7' C6' H6' 119.6 . . ? C6' C7' C8' 120.52(17) . . ? C6' C7' H7' 119.7 . . ? C8' C7' H7' 119.7 . . ? C8A' C8' C7' 118.97(15) . . ? C8A' C8' H8' 120.5 . . ? C7' C8' H8' 120.5 . . ? O2 C9' C10' 105.91(11) . . ? O2 C9' C1A' 111.47(13) . . ? C10' C9' C1A' 114.84(13) . . ? O2 C9' C8A' 111.18(12) . . ? C10' C9' C8A' 112.29(13) . . ? C1A' C9' C8A' 101.29(12) . . ? C12' C10' C11' 117.66(14) . . ? C12' C10' C9' 122.62(13) . . ? C11' C10' C9' 119.72(13) . . ? C12 C11' C10' 121.02(14) . . ? C12 C11' H11' 119.5 . . ? C10' C11' H11' 119.5 . . ? C11 C12' C10' 121.23(14) . . ? C11 C12' H12' 119.4 . . ? C10' C12' H12' 119.4 . . ? C1 C1A C4A 120.71(15) . . ? C1 C1A C9 128.65(14) . . ? C4A C1A C9 110.63(14) . . ? C4 C4A C1A 119.97(16) . . ? C4 C4A C5A 131.23(15) . . ? C1A C4A C5A 108.78(13) . . ? C5 C5A C8A 120.31(16) . . ? C5 C5A C4A 131.07(15) . . ? C8A C5A C4A 108.59(14) . . ? C8 C8A C5A 120.69(15) . . ? C8 C8A C9 128.77(14) . . ? C5A C8A C9 110.53(14) . . ? C1' C1A' C4A' 120.62(15) . . ? C1' C1A' C9' 128.68(14) . . ? C4A' C1A' C9' 110.61(14) . . ? C4' C4A' C1A' 119.98(16) . . ? C4' C4A' C5A' 131.14(15) . . ? C1A' C4A' C5A' 108.83(14) . . ? C5' C5A' C8A' 120.42(16) . . ? C5' C5A' C4A' 130.97(15) . . ? C8A' C5A' C4A' 108.58(14) . . ? C8' C8A' C5A' 120.50(15) . . ? C8' C8A' C9' 128.77(14) . . ? C5A' C8A' C9' 110.68(14) . . ? C2G1 N1G1 C6G1 117.03(15) . . ? N1G1 C2G1 C3G1 124.72(15) . . ? N1G1 C2G1 H2G1 117.6 . . ? C3G1 C2G1 H2G1 117.6 . . ? C4G1 C3G1 C2G1 116.51(16) . . ? C4G1 C3G1 C7G1 122.51(15) . . ? C2G1 C3G1 C7G1 120.95(15) . . ? C5G1 C4G1 C3G1 119.74(15) . . ? C5G1 C4G1 H4G1 120.1 . . ? C3G1 C4G1 H4G1 120.1 . . ? C6G1 C5G1 C4G1 119.33(15) . . ? C6G1 C5G1 H5G1 120.3 . . ? C4G1 C5G1 H5G1 120.3 . . ? N1G1 C6G1 C5G1 122.66(17) . . ? N1G1 C6G1 H6G1 118.7 . . ? C5G1 C6G1 H6G1 118.7 . . ? C3G1 C7G1 H7GA 109.5 . . ? C3G1 C7G1 H7GC 109.5 . . ? H7GA C7G1 H7GC 109.5 . . ? C3G1 C7G1 H7GB 109.5 . . ? H7GA C7G1 H7GB 109.5 . . ? H7GC C7G1 H7GB 109.5 . . ? C6G2 N1G2 C2G2 117.66(16) . . ? N1G2 C2G2 C3G2 124.20(17) . . ? N1G2 C2G2 H2G2 117.9 . . ? C3G2 C2G2 H2G2 117.9 . . ? C2G2 C3G2 C4G2 116.84(18) . . ? C2G2 C3G2 C7G2 121.21(17) . . ? C4G2 C3G2 C7G2 121.94(16) . . ? C5G2 C4G2 C3G2 119.64(16) . . ? C5G2 C4G2 H4G2 120.2 . . ? C3G2 C4G2 H4G2 120.2 . . ? C6G2 C5G2 C4G2 119.34(17) . . ? C6G2 C5G2 H5G2 120.3 . . ? C4G2 C5G2 H5G2 120.3 . . ? N1G2 C6G2 C5G2 122.31(18) . . ? N1G2 C6G2 H6G2 118.8 . . ? C5G2 C6G2 H6G2 118.8 . . ? C3G2 C7G2 H7GD 109.5 . . ? C3G2 C7G2 H7GE 109.5 . . ? H7GD C7G2 H7GE 109.5 . . ? C3G2 C7G2 H7GF 109.5 . . ? H7GD C7G2 H7GF 109.5 . . ? H7GE C7G2 H7GF 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 C1A C1 C2 C3 -0.8(2) . . . . ? C1 C2 C3 C4 0.3(2) . . . . ? C2 C3 C4 C4A 0.6(2) . . . . ? C5A C5 C6 C7 -0.2(3) . . . . ? C5 C6 C7 C8 0.5(3) . . . . ? C6 C7 C8 C8A -0.5(2) . . . . ? O1 C9 C10 C12 144.54(14) . . . . ? C1A C9 C10 C12 18.2(2) . . . . ? C8A C9 C10 C12 -95.65(18) . . . . ? O1 C9 C10 C11 -36.9(2) . . . . ? C1A C9 C10 C11 -163.22(14) . . . . ? C8A C9 C10 C11 82.95(17) . . . . ? C12 C10 C11 C12' 0.3(2) . . . . ? C9 C10 C11 C12' -178.36(14) . . . . ? C11 C10 C12 C11' -0.5(2) . . . . ? C9 C10 C12 C11' 178.09(14) . . . . ? C1A' C1' C2' C3' 0.4(2) . . . . ? C1' C2' C3' C4' 0.3(3) . . . . ? C2' C3' C4' C4A' -0.9(3) . . . . ? C5A' C5' C6' C7' -0.3(3) . . . . ? C5' C6' C7' C8' -0.7(3) . . . . ? C6' C7' C8' C8A' 0.9(2) . . . . ? O2 C9' C10' C12' -139.06(14) . . . . ? C1A' C9' C10' C12' -15.6(2) . . . . ? C8A' C9' C10' C12' 99.41(18) . . . . ? O2 C9' C10' C11' 40.8(2) . . . . ? C1A' C9' C10' C11' 164.25(14) . . . . ? C8A' C9' C10' C11' -80.74(17) . . . . ? C10 C12 C11' C10' 0.2(2) . . . . ? C12' C10' C11' C12 0.3(2) . . . . ? C9' C10' C11' C12 -179.54(14) . . . . ? C10 C11 C12' C10' 0.3(2) . . . . ? C11' C10' C12' C11 -0.6(2) . . . . ? C9' C10' C12' C11 179.28(14) . . . . ? C2 C1 C1A C4A 0.4(2) . . . . ? C2 C1 C1A C9 178.85(14) . . . . ? O1 C9 C1A C1 -63.9(2) . . . . ? C10 C9 C1A C1 61.8(2) . . . . ? C8A C9 C1A C1 -178.45(15) . . . . ? O1 C9 C1A C4A 114.67(14) . . . . ? C10 C9 C1A C4A -119.66(14) . . . . ? C8A C9 C1A C4A 0.11(16) . . . . ? C3 C4 C4A C1A -0.9(2) . . . . ? C3 C4 C4A C5A -179.29(16) . . . . ? C1 C1A C4A C4 0.4(2) . . . . ? C9 C1A C4A C4 -178.24(13) . . . . ? C1 C1A C4A C5A 179.13(14) . . . . ? C9 C1A C4A C5A 0.44(17) . . . . ? C6 C5 C5A C8A -0.1(2) . . . . ? C6 C5 C5A C4A 177.79(16) . . . . ? C4 C4A C5A C5 -0.5(3) . . . . ? C1A C4A C5A C5 -178.99(16) . . . . ? C4 C4A C5A C8A 177.62(16) . . . . ? C1A C4A C5A C8A -0.86(17) . . . . ? C7 C8 C8A C5A 0.1(2) . . . . ? C7 C8 C8A C9 -178.82(15) . . . . ? C5 C5A C8A C8 0.2(2) . . . . ? C4A C5A C8A C8 -178.17(14) . . . . ? C5 C5A C8A C9 179.31(14) . . . . ? C4A C5A C8A C9 0.95(17) . . . . ? O1 C9 C8A C8 60.9(2) . . . . ? C10 C9 C8A C8 -60.6(2) . . . . ? C1A C9 C8A C8 178.37(15) . . . . ? O1 C9 C8A C5A -118.16(13) . . . . ? C10 C9 C8A C5A 120.42(14) . . . . ? C1A C9 C8A C5A -0.65(16) . . . . ? C2' C1' C1A' C4A' -0.4(2) . . . . ? C2' C1' C1A' C9' -176.77(15) . . . . ? O2 C9' C1A' C1' 58.6(2) . . . . ? C10' C9' C1A' C1' -61.8(2) . . . . ? C8A' C9' C1A' C1' 176.97(15) . . . . ? O2 C9' C1A' C4A' -117.98(14) . . . . ? C10' C9' C1A' C4A' 121.58(14) . . . . ? C8A' C9' C1A' C4A' 0.34(16) . . . . ? C3' C4' C4A' C1A' 0.9(2) . . . . ? C3' C4' C4A' C5A' 177.92(16) . . . . ? C1' C1A' C4A' C4' -0.2(2) . . . . ? C9' C1A' C4A' C4' 176.75(14) . . . . ? C1' C1A' C4A' C5A' -177.83(14) . . . . ? C9' C1A' C4A' C5A' -0.90(17) . . . . ? C6' C5' C5A' C8A' 1.1(2) . . . . ? C6' C5' C5A' C4A' -176.29(16) . . . . ? C4' C4A' C5A' C5' 1.5(3) . . . . ? C1A' C4A' C5A' C5' 178.78(17) . . . . ? C4' C4A' C5A' C8A' -176.17(16) . . . . ? C1A' C4A' C5A' C8A' 1.13(18) . . . . ? C7' C8' C8A' C5A' -0.1(2) . . . . ? C7' C8' C8A' C9' 177.43(15) . . . . ? C5' C5A' C8A' C8' -0.9(2) . . . . ? C4A' C5A' C8A' C8' 177.03(14) . . . . ? C5' C5A' C8A' C9' -178.86(14) . . . . ? C4A' C5A' C8A' C9' -0.91(17) . . . . ? O2 C9' C8A' C8' -58.8(2) . . . . ? C10' C9' C8A' C8' 59.6(2) . . . . ? C1A' C9' C8A' C8' -177.36(15) . . . . ? O2 C9' C8A' C5A' 118.90(14) . . . . ? C10' C9' C8A' C5A' -122.64(14) . . . . ? C1A' C9' C8A' C5A' 0.37(16) . . . . ? C6G1 N1G1 C2G1 C3G1 -0.2(3) . . . . ? N1G1 C2G1 C3G1 C4G1 -0.7(3) . . . . ? N1G1 C2G1 C3G1 C7G1 -179.19(17) . . . . ? C2G1 C3G1 C4G1 C5G1 1.2(2) . . . . ? C7G1 C3G1 C4G1 C5G1 179.70(17) . . . . ? C3G1 C4G1 C5G1 C6G1 -0.9(3) . . . . ? C2G1 N1G1 C6G1 C5G1 0.5(3) . . . . ? C4G1 C5G1 C6G1 N1G1 0.0(3) . . . . ? C6G2 N1G2 C2G2 C3G2 0.3(3) . . . . ? N1G2 C2G2 C3G2 C4G2 -0.4(3) . . . . ? N1G2 C2G2 C3G2 C7G2 178.64(17) . . . . ? C2G2 C3G2 C4G2 C5G2 0.4(3) . . . . ? C7G2 C3G2 C4G2 C5G2 -178.69(17) . . . . ? C3G2 C4G2 C5G2 C6G2 -0.3(3) . . . . ? C2G2 N1G2 C6G2 C5G2 -0.2(3) . . . . ? C4G2 C5G2 C6G2 N1G2 0.2(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1O N1G1 0.932(16) 1.897(16) 2.8230(18) 172(2) . O2 H2O N1G2 0.971(15) 1.772(16) 2.7400(18) 175(2) . _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.29 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.158 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.046 # Attachment '- H4PIC.CIF' data_h4pic _database_code_depnum_ccdc_archive 'CCDC 817292' #TrackingRef '- H4PIC.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1,4-bis(9-hydroxyfluoren-9-yl)benzene. 4-picoline clathrate' ; _chemical_name_common "'1,4-bis(9-hydroxyfluoren-9-yl)benzene. 4-picoline clathrate'" _chemical_melting_point 264-265 _chemical_formula_moiety 'C32 H22 O2, 2(C6 H7 N)' _chemical_formula_sum 'C44 H36 N2 O2' _chemical_formula_weight 624.75 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 triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.15290(10) _cell_length_b 8.48480(10) _cell_length_c 12.4124(3) _cell_angle_alpha 93.6150(10) _cell_angle_beta 90.8030(10) _cell_angle_gamma 103.7880(10) _cell_volume 831.86(2) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3046 _cell_measurement_theta_min 3.5 _cell_measurement_theta_max 27.9 _exptl_crystal_description 'clear blocks' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.247 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 330 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type none _exptl_special_details ; Distance of O1-H1O is c=restrainted to 0.97(1) angstroms. ; _diffrn_ambient_temperature 173(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 Kappa CCD' _diffrn_measurement_method 'Combination of phi and omega' _diffrn_reflns_number 7420 _diffrn_reflns_av_R_equivalents 0.0181 _diffrn_reflns_av_sigmaI/netI 0.0386 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.48 _diffrn_reflns_theta_max 27.85 _reflns_number_total 3938 _reflns_number_gt 3046 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 2000)' _computing_cell_refinement 'Collect (Nonius, 2000)' _computing_data_reduction 'Collect (Nonius, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSEED, graphical interface to SHELX (1999)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0575P)^2^+0.1128P] 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 none _refine_ls_number_reflns 3938 _refine_ls_number_parameters 222 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0598 _refine_ls_R_factor_gt 0.0424 _refine_ls_wR_factor_ref 0.1120 _refine_ls_wR_factor_gt 0.1054 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _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 0.32005(10) 0.48901(9) 0.77553(6) 0.01971(19) Uani 1 1 d D . . H1O H 0.4354(13) 0.523(2) 0.8026(13) 0.056(5) Uiso 1 1 d D . . C1 C 0.48411(15) 0.18335(14) 0.76694(9) 0.0222(3) Uani 1 1 d . . . H1 H 0.5813 0.2701 0.7810 0.027 Uiso 1 1 calc R . . C2 C 0.48461(16) 0.02607(15) 0.79418(10) 0.0263(3) Uani 1 1 d . . . H2 H 0.5825 0.0062 0.8277 0.032 Uiso 1 1 calc R . . C3 C 0.34348(17) -0.10118(14) 0.77264(10) 0.0282(3) Uani 1 1 d . . . H3 H 0.3455 -0.2074 0.7917 0.034 Uiso 1 1 calc R . . C4 C 0.19944(16) -0.07475(14) 0.72347(10) 0.0258(3) Uani 1 1 d . . . H4 H 0.1035 -0.1623 0.7076 0.031 Uiso 1 1 calc R . . C5 C -0.10358(15) 0.06909(16) 0.62029(10) 0.0278(3) Uani 1 1 d . . . H5 H -0.1430 -0.0455 0.6219 0.033 Uiso 1 1 calc R . . C6 C -0.20917(16) 0.16254(17) 0.58453(10) 0.0314(3) Uani 1 1 d . . . H6 H -0.3214 0.1112 0.5605 0.038 Uiso 1 1 calc R . . C7 C -0.15247(16) 0.33061(16) 0.58353(10) 0.0288(3) Uani 1 1 d . . . H7 H -0.2268 0.3931 0.5598 0.035 Uiso 1 1 calc R . . C8 C 0.01270(15) 0.40822(15) 0.61704(9) 0.0238(3) Uani 1 1 d . . . H8 H 0.0515 0.5230 0.6165 0.029 Uiso 1 1 calc R . . C9 C 0.30469(14) 0.37143(12) 0.68697(9) 0.0168(2) Uani 1 1 d . . . C10 C 0.41056(13) 0.43885(12) 0.59118(9) 0.0161(2) Uani 1 1 d . . . C11 C 0.49716(14) 0.60179(13) 0.59154(9) 0.0187(2) Uani 1 1 d . . . H11 H 0.4962 0.6729 0.6537 0.022 Uiso 1 1 calc R . . C12 C 0.41500(14) 0.33893(13) 0.49858(9) 0.0183(2) Uani 1 1 d . . . H12 H 0.3567 0.2275 0.4968 0.022 Uiso 1 1 calc R . . C1A C 0.34055(14) 0.21059(13) 0.71946(9) 0.0181(2) Uani 1 1 d . . . C4A C 0.19783(15) 0.08196(13) 0.69782(9) 0.0199(2) Uani 1 1 d . . . C5A C 0.06113(14) 0.14643(14) 0.65371(9) 0.0206(2) Uani 1 1 d . . . C8A C 0.11874(14) 0.31519(13) 0.65100(9) 0.0188(2) Uani 1 1 d . . . N1G N 0.64934(13) 0.61613(13) 0.86402(8) 0.0292(3) Uani 1 1 d . . . C2G C 0.79263(17) 0.58480(16) 0.82771(11) 0.0326(3) Uani 1 1 d . . . H2G H 0.7881 0.5249 0.7600 0.039 Uiso 1 1 calc R . . C3G C 0.94694(17) 0.63400(16) 0.88238(12) 0.0345(3) Uani 1 1 d . . . H3G H 1.0440 0.6051 0.8537 0.041 Uiso 1 1 calc R . . C4G C 0.95831(18) 0.72614(17) 0.97977(11) 0.0366(3) Uani 1 1 d . . . C5G C 0.81073(19) 0.76231(19) 1.01642(11) 0.0418(4) Uani 1 1 d . . . H5G H 0.8126 0.8272 1.0819 0.050 Uiso 1 1 calc R . . C6G C 0.66127(18) 0.70405(17) 0.95782(10) 0.0350(3) Uani 1 1 d . . . H6G H 0.5614 0.7279 0.9859 0.042 Uiso 1 1 calc R . . C7G C 1.1239(2) 0.7850(2) 1.04213(15) 0.0633(6) Uani 1 1 d . . . H7GA H 1.1031 0.7867 1.1197 0.095 Uiso 1 1 calc R . . H7GB H 1.1787 0.8950 1.0228 0.095 Uiso 1 1 calc R . . H7GC H 1.1975 0.7117 1.0244 0.095 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 0.0223(4) 0.0175(4) 0.0185(4) -0.0009(3) 0.0011(3) 0.0037(3) C1 0.0212(6) 0.0214(6) 0.0241(6) 0.0039(5) 0.0023(5) 0.0049(4) C2 0.0289(7) 0.0274(6) 0.0266(6) 0.0064(5) 0.0038(5) 0.0132(5) C3 0.0396(8) 0.0178(6) 0.0298(7) 0.0058(5) 0.0097(5) 0.0107(5) C4 0.0310(7) 0.0177(6) 0.0262(6) 0.0002(5) 0.0044(5) 0.0009(5) C5 0.0225(6) 0.0296(6) 0.0264(6) -0.0021(5) 0.0007(5) -0.0022(5) C6 0.0183(6) 0.0447(8) 0.0269(7) -0.0025(6) -0.0005(5) 0.0001(5) C7 0.0209(6) 0.0430(8) 0.0242(6) 0.0031(5) 0.0013(5) 0.0109(5) C8 0.0214(6) 0.0283(6) 0.0224(6) 0.0036(5) 0.0036(5) 0.0068(5) C9 0.0176(5) 0.0156(5) 0.0168(5) 0.0007(4) 0.0007(4) 0.0036(4) C10 0.0133(5) 0.0171(5) 0.0185(5) 0.0035(4) -0.0006(4) 0.0040(4) C11 0.0202(6) 0.0169(5) 0.0180(5) -0.0008(4) 0.0000(4) 0.0029(4) C12 0.0182(6) 0.0135(5) 0.0216(6) 0.0014(4) -0.0003(4) 0.0009(4) C1A 0.0217(6) 0.0170(5) 0.0155(5) 0.0017(4) 0.0039(4) 0.0043(4) C4A 0.0234(6) 0.0181(5) 0.0170(5) -0.0002(4) 0.0036(4) 0.0023(4) C5A 0.0200(6) 0.0231(6) 0.0167(5) 0.0004(4) 0.0034(4) 0.0014(4) C8A 0.0177(6) 0.0230(6) 0.0150(5) 0.0017(4) 0.0037(4) 0.0034(4) N1G 0.0268(6) 0.0331(6) 0.0242(5) -0.0016(4) 0.0006(4) 0.0012(4) C2G 0.0312(7) 0.0293(7) 0.0328(7) -0.0058(5) 0.0052(6) 0.0000(5) C3G 0.0251(7) 0.0281(7) 0.0483(8) 0.0081(6) 0.0036(6) 0.0009(5) C4G 0.0337(8) 0.0384(8) 0.0306(7) 0.0162(6) -0.0076(6) -0.0086(6) C5G 0.0444(9) 0.0509(9) 0.0192(6) -0.0025(6) 0.0014(6) -0.0090(7) C6G 0.0326(7) 0.0426(8) 0.0260(7) -0.0042(6) 0.0057(5) 0.0028(6) C7G 0.0447(10) 0.0735(12) 0.0572(11) 0.0269(9) -0.0239(8) -0.0188(9) _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 C9 1.4205(13) . ? O1 H1O 0.964(9) . ? C1 C1A 1.3775(16) . ? C1 C2 1.3981(16) . ? C1 H1 0.9500 . ? C2 C3 1.3870(18) . ? C2 H2 0.9500 . ? C3 C4 1.3873(18) . ? C3 H3 0.9500 . ? C4 C4A 1.3897(16) . ? C4 H4 0.9500 . ? C5 C6 1.3877(19) . ? C5 C5A 1.3914(16) . ? C5 H5 0.9500 . ? C6 C7 1.3913(19) . ? C6 H6 0.9500 . ? C7 C8 1.3953(17) . ? C7 H7 0.9500 . ? C8 C8A 1.3803(16) . ? C8 H8 0.9500 . ? C9 C8A 1.5280(15) . ? C9 C10 1.5378(15) . ? C9 C1A 1.5384(14) . ? C10 C12 1.3907(15) . ? C10 C11 1.3942(15) . ? C11 C12 1.3925(15) 2_666 ? C11 H11 0.9500 . ? C12 C11 1.3925(15) 2_666 ? C12 H12 0.9500 . ? C1A C4A 1.4022(15) . ? C4A C5A 1.4670(17) . ? C5A C8A 1.3993(16) . ? N1G C6G 1.3320(16) . ? N1G C2G 1.3365(17) . ? C2G C3G 1.3811(19) . ? C2G H2G 0.9500 . ? C3G C4G 1.387(2) . ? C3G H3G 0.9500 . ? C4G C5G 1.387(2) . ? C4G C7G 1.507(2) . ? C5G C6G 1.3787(19) . ? C5G H5G 0.9500 . ? C6G H6G 0.9500 . ? C7G H7GA 0.9800 . ? C7G H7GB 0.9800 . ? C7G H7GC 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 O1 H1O 110.7(10) . . ? C1A C1 C2 119.01(11) . . ? C1A C1 H1 120.5 . . ? C2 C1 H1 120.5 . . ? C3 C2 C1 120.59(11) . . ? C3 C2 H2 119.7 . . ? C1 C2 H2 119.7 . . ? C2 C3 C4 120.60(11) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C3 C4 C4A 118.88(11) . . ? C3 C4 H4 120.6 . . ? C4A C4 H4 120.6 . . ? C6 C5 C5A 118.72(12) . . ? C6 C5 H5 120.6 . . ? C5A C5 H5 120.6 . . ? C5 C6 C7 120.74(11) . . ? C5 C6 H6 119.6 . . ? C7 C6 H6 119.6 . . ? C6 C7 C8 120.55(12) . . ? C6 C7 H7 119.7 . . ? C8 C7 H7 119.7 . . ? C8A C8 C7 118.79(11) . . ? C8A C8 H8 120.6 . . ? C7 C8 H8 120.6 . . ? O1 C9 C8A 108.72(9) . . ? O1 C9 C10 112.23(8) . . ? C8A C9 C10 109.52(8) . . ? O1 C9 C1A 112.79(8) . . ? C8A C9 C1A 100.98(8) . . ? C10 C9 C1A 111.94(9) . . ? C12 C10 C11 117.96(10) . . ? C12 C10 C9 120.16(9) . . ? C11 C10 C9 121.79(9) . . ? C12 C11 C10 120.45(10) 2_666 . ? C12 C11 H11 119.8 2_666 . ? C10 C11 H11 119.8 . . ? C10 C12 C11 121.59(10) . 2_666 ? C10 C12 H12 119.2 . . ? C11 C12 H12 119.2 2_666 . ? C1 C1A C4A 120.39(10) . . ? C1 C1A C9 129.21(10) . . ? C4A C1A C9 110.37(9) . . ? C4 C4A C1A 120.52(11) . . ? C4 C4A C5A 130.46(11) . . ? C1A C4A C5A 108.93(9) . . ? C5 C5A C8A 120.44(11) . . ? C5 C5A C4A 131.05(11) . . ? C8A C5A C4A 108.49(10) . . ? C8 C8A C5A 120.74(11) . . ? C8 C8A C9 128.20(10) . . ? C5A C8A C9 111.05(10) . . ? C6G N1G C2G 116.30(11) . . ? N1G C2G C3G 124.16(12) . . ? N1G C2G H2G 117.9 . . ? C3G C2G H2G 117.9 . . ? C2G C3G C4G 119.12(13) . . ? C2G C3G H3G 120.4 . . ? C4G C3G H3G 120.4 . . ? C5G C4G C3G 116.88(12) . . ? C5G C4G C7G 121.72(15) . . ? C3G C4G C7G 121.39(15) . . ? C6G C5G C4G 119.96(13) . . ? C6G C5G H5G 120.0 . . ? C4G C5G H5G 120.0 . . ? N1G C6G C5G 123.54(13) . . ? N1G C6G H6G 118.2 . . ? C5G C6G H6G 118.2 . . ? C4G C7G H7GA 109.5 . . ? C4G C7G H7GB 109.5 . . ? H7GA C7G H7GB 109.5 . . ? C4G C7G H7GC 109.5 . . ? H7GA C7G H7GC 109.5 . . ? H7GB C7G H7GC 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 C1A C1 C2 C3 0.74(18) . . . . ? C1 C2 C3 C4 0.15(19) . . . . ? C2 C3 C4 C4A -1.10(18) . . . . ? C5A C5 C6 C7 -0.92(19) . . . . ? C5 C6 C7 C8 0.94(19) . . . . ? C6 C7 C8 C8A 0.10(18) . . . . ? O1 C9 C10 C12 177.97(9) . . . . ? C8A C9 C10 C12 -61.18(12) . . . . ? C1A C9 C10 C12 49.97(13) . . . . ? O1 C9 C10 C11 -5.39(14) . . . . ? C8A C9 C10 C11 115.46(11) . . . . ? C1A C9 C10 C11 -133.39(11) . . . . ? C12 C10 C11 C12 -0.03(17) . . . 2_666 ? C9 C10 C11 C12 -176.74(10) . . . 2_666 ? C11 C10 C12 C11 0.03(18) . . . 2_666 ? C9 C10 C12 C11 176.80(10) . . . 2_666 ? C2 C1 C1A C4A -0.66(17) . . . . ? C2 C1 C1A C9 176.84(11) . . . . ? O1 C9 C1A C1 -58.45(15) . . . . ? C8A C9 C1A C1 -174.31(11) . . . . ? C10 C9 C1A C1 69.26(14) . . . . ? O1 C9 C1A C4A 119.24(10) . . . . ? C8A C9 C1A C4A 3.39(11) . . . . ? C10 C9 C1A C4A -113.05(10) . . . . ? C3 C4 C4A C1A 1.18(17) . . . . ? C3 C4 C4A C5A -174.94(11) . . . . ? C1 C1A C4A C4 -0.30(17) . . . . ? C9 C1A C4A C4 -178.23(10) . . . . ? C1 C1A C4A C5A 176.57(10) . . . . ? C9 C1A C4A C5A -1.36(12) . . . . ? C6 C5 C5A C8A -0.11(17) . . . . ? C6 C5 C5A C4A 177.91(12) . . . . ? C4 C4A C5A C5 -3.3(2) . . . . ? C1A C4A C5A C5 -179.74(12) . . . . ? C4 C4A C5A C8A 174.92(12) . . . . ? C1A C4A C5A C8A -1.54(13) . . . . ? C7 C8 C8A C5A -1.14(17) . . . . ? C7 C8 C8A C9 177.52(11) . . . . ? C5 C5A C8A C8 1.16(17) . . . . ? C4A C5A C8A C8 -177.27(10) . . . . ? C5 C5A C8A C9 -177.71(10) . . . . ? C4A C5A C8A C9 3.86(12) . . . . ? O1 C9 C8A C8 58.02(14) . . . . ? C10 C9 C8A C8 -64.94(14) . . . . ? C1A C9 C8A C8 176.85(11) . . . . ? O1 C9 C8A C5A -123.22(9) . . . . ? C10 C9 C8A C5A 113.82(10) . . . . ? C1A C9 C8A C5A -4.38(11) . . . . ? C6G N1G C2G C3G 1.71(19) . . . . ? N1G C2G C3G C4G -2.1(2) . . . . ? C2G C3G C4G C5G 0.37(19) . . . . ? C2G C3G C4G C7G -179.17(13) . . . . ? C3G C4G C5G C6G 1.4(2) . . . . ? C7G C4G C5G C6G -179.01(14) . . . . ? C2G N1G C6G C5G 0.3(2) . . . . ? C4G C5G C6G N1G -1.9(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1O N1G 0.964(9) 1.865(9) 2.8222(13) 171.3(16) . _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.85 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.272 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.048 # Attachment 'HMIX.CIF' data_hmix _database_code_depnum_ccdc_archive 'CCDC 817293' #TrackingRef 'HMIX.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1,4-bis(9-hydroxyfluoren-9-yl)benzene. 4-picoline and morpholine clathrate' ; _chemical_name_common none _chemical_melting_point 'not measured' _chemical_formula_moiety '2(C32 H22 O2), 2(C6 H7 N), 2(C4 H9 N O)' _chemical_formula_sum 'C84 H76 N4 O6' _chemical_formula_weight 1237.49 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 c2/c 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 16.8977(2) _cell_length_b 13.9004(2) _cell_length_c 28.3312(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.1030(10) _cell_angle_gamma 90.00 _cell_volume 6654.56(16) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 21801 _cell_measurement_theta_min 3.44 _cell_measurement_theta_max 26.53 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.235 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2624 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type none _exptl_special_details ; Unstable without mother liquor under atmospheric conditions. Crystal coated with Paratone oil. ; _diffrn_ambient_temperature 173(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 Kappa CCD' _diffrn_measurement_method 'Combination of phi and omega' _diffrn_reflns_number 21801 _diffrn_reflns_av_R_equivalents 0.0476 _diffrn_reflns_av_sigmaI/netI 0.0497 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 3.44 _diffrn_reflns_theta_max 26.53 _reflns_number_total 6135 _reflns_number_gt 4111 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 2000)' _computing_cell_refinement 'Collect (Nonius, 2000)' _computing_data_reduction 'Collect (Nonius, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSEED, graphical interface to SHELX (1999)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0686P)^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 SHELXL _refine_ls_extinction_coef 0.0047(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6135 _refine_ls_number_parameters 438 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0803 _refine_ls_R_factor_gt 0.0441 _refine_ls_wR_factor_ref 0.1167 _refine_ls_wR_factor_gt 0.1029 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _refine_ls_shift/su_max 0.001 _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 C1AX C 0.04102(9) 0.75158(11) 0.55061(6) 0.0308(4) Uani 1 1 d . . . C4AX C -0.01223(9) 0.67597(11) 0.54495(6) 0.0313(4) Uani 1 1 d . . . C5AX C -0.01562(9) 0.64991(10) 0.49482(6) 0.0295(4) Uani 1 1 d . . . C8AX C 0.03552(8) 0.70998(11) 0.46974(5) 0.0275(4) Uani 1 1 d . . . C1AY C 0.20154(8) 0.59265(10) 0.29754(5) 0.0236(3) Uani 1 1 d . . . C4AY C 0.24575(8) 0.66567(10) 0.27607(5) 0.0251(4) Uani 1 1 d . . . C5AY C 0.25042(8) 0.64557(10) 0.22506(5) 0.0262(4) Uani 1 1 d . . . C8AY C 0.20892(8) 0.56051(10) 0.21585(5) 0.0250(4) Uani 1 1 d . . . O1G1 O -0.25354(6) 0.85246(8) 0.45623(4) 0.0481(3) Uani 1 1 d . . . N1G1 N -0.09486(7) 0.91240(10) 0.47824(5) 0.0342(3) Uani 1 1 d D . . H1G1 H -0.0945(11) 0.9801(7) 0.4823(6) 0.064(6) Uiso 1 1 d D . . C1G1 C -0.20763(11) 0.90274(15) 0.42240(7) 0.0539(5) Uani 1 1 d . . . H1GB H -0.2191 0.9724 0.4246 0.065 Uiso 1 1 calc R . . H1GA H -0.2224 0.8809 0.3903 0.065 Uiso 1 1 calc R . . C2G1 C -0.12012(10) 0.88603(14) 0.43022(6) 0.0459(5) Uani 1 1 d . . . H2GB H -0.1079 0.8173 0.4246 0.055 Uiso 1 1 calc R . . H2GA H -0.0897 0.9245 0.4071 0.055 Uiso 1 1 calc R . . C3G1 C -0.14680(9) 0.86711(12) 0.51281(6) 0.0382(4) Uani 1 1 d . . . H3GB H -0.1343 0.8930 0.5445 0.046 Uiso 1 1 calc R . . H3GA H -0.1361 0.7971 0.5134 0.046 Uiso 1 1 calc R . . C4G1 C -0.23344(10) 0.88299(13) 0.50270(6) 0.0420(4) Uani 1 1 d . . . H4GA H -0.2655 0.8468 0.5259 0.050 Uiso 1 1 calc R . . H4GB H -0.2460 0.9522 0.5062 0.050 Uiso 1 1 calc R . . N1G2 N 0.35877(8) 0.42878(10) 0.29672(5) 0.0466(4) Uani 1 1 d . . . C2G2 C 0.39471(10) 0.34484(13) 0.30222(6) 0.0417(4) Uani 1 1 d . . . H2G2 H 0.3641 0.2880 0.2987 0.050 Uiso 1 1 calc R . . C3G2 C 0.47368(9) 0.33516(12) 0.31277(6) 0.0403(4) Uani 1 1 d . . . H3G2 H 0.4961 0.2728 0.3160 0.048 Uiso 1 1 calc R . . C4G2 C 0.52019(10) 0.41492(12) 0.31870(6) 0.0398(4) Uani 1 1 d . . . C5G2 C 0.48324(11) 0.50150(14) 0.31368(9) 0.0711(7) Uani 1 1 d . . . H4G2 H 0.5125 0.5594 0.3175 0.085 Uiso 1 1 calc R . . C6G2 C 0.40399(12) 0.50547(15) 0.30316(9) 0.0730(7) Uani 1 1 d . . . H5G2 H 0.3801 0.5671 0.3003 0.088 Uiso 1 1 calc R . . C7G2 C 0.60668(10) 0.40795(16) 0.33061(8) 0.0664(6) Uani 1 1 d . . . H7GA H 0.6139 0.4155 0.3647 0.100 Uiso 1 1 calc R . . H7GC H 0.6357 0.4588 0.3141 0.100 Uiso 1 1 calc R . . H7GB H 0.6269 0.3450 0.3208 0.100 Uiso 1 1 calc R . . O1X O 0.06274(6) 0.87831(7) 0.49143(4) 0.0378(3) Uani 1 1 d D . . H1OX H 0.0055(6) 0.8900(13) 0.4894(7) 0.076(6) Uiso 1 1 d D . . C1X C 0.05438(10) 0.79002(13) 0.59472(6) 0.0441(5) Uani 1 1 d . . . H1X H 0.0901 0.8421 0.5989 0.053 Uiso 1 1 calc R . . C2X C 0.01434(12) 0.75083(15) 0.63313(7) 0.0545(6) Uani 1 1 d . . . H2X H 0.0237 0.7760 0.6638 0.065 Uiso 1 1 calc R . . C3X C -0.03845(12) 0.67636(16) 0.62742(7) 0.0548(5) Uani 1 1 d . . . H3X H -0.0651 0.6508 0.6541 0.066 Uiso 1 1 calc R . . C4X C -0.05301(10) 0.63857(13) 0.58320(6) 0.0432(5) Uani 1 1 d . . . H4X H -0.0902 0.5880 0.5791 0.052 Uiso 1 1 calc R . . C5X C -0.05903(9) 0.57960(11) 0.47145(6) 0.0393(4) Uani 1 1 d . . . H5X H -0.0939 0.5386 0.4883 0.047 Uiso 1 1 calc R . . C6X C -0.05053(10) 0.57059(12) 0.42345(7) 0.0440(5) Uani 1 1 d . . . H6X H -0.0794 0.5222 0.4071 0.053 Uiso 1 1 calc R . . C7X C -0.00092(10) 0.63047(13) 0.39855(6) 0.0445(5) Uani 1 1 d . . . H7X H 0.0034 0.6235 0.3653 0.053 Uiso 1 1 calc R . . C8X C 0.04305(9) 0.70110(12) 0.42158(6) 0.0364(4) Uani 1 1 d . . . H8X H 0.0775 0.7422 0.4044 0.044 Uiso 1 1 calc R . . C9X C 0.07755(8) 0.78039(10) 0.50322(5) 0.0292(4) Uani 1 1 d . . . C10X C 0.16723(9) 0.76546(10) 0.50205(5) 0.0283(4) Uani 1 1 d . . . C11X C 0.21708(9) 0.83126(11) 0.48010(6) 0.0316(4) Uani 1 1 d . . . H11X H 0.1952 0.8875 0.4662 0.038 Uiso 1 1 calc R . . C12X C 0.20183(9) 0.68379(11) 0.52184(6) 0.0319(4) Uani 1 1 d . . . H12X H 0.1692 0.6375 0.5370 0.038 Uiso 1 1 calc R . . O1Y O 0.19858(6) 0.42479(7) 0.27161(4) 0.0308(3) Uani 1 1 d D . . H1OY H 0.2553(6) 0.4311(13) 0.2783(6) 0.069(6) Uiso 1 1 d D . . C1Y C 0.19179(9) 0.59073(11) 0.34575(5) 0.0298(4) Uani 1 1 d . . . H1Y H 0.1622 0.5408 0.3603 0.036 Uiso 1 1 calc R . . C2Y C 0.22607(9) 0.66318(11) 0.37284(6) 0.0342(4) Uani 1 1 d . . . H2Y H 0.2208 0.6620 0.4062 0.041 Uiso 1 1 calc R . . C3Y C 0.26768(9) 0.73684(11) 0.35151(6) 0.0334(4) Uani 1 1 d . . . H3Y H 0.2895 0.7867 0.3704 0.040 Uiso 1 1 calc R . . C4Y C 0.27821(9) 0.73922(11) 0.30299(6) 0.0311(4) Uani 1 1 d . . . H4Y H 0.3070 0.7900 0.2885 0.037 Uiso 1 1 calc R . . C5Y C 0.28745(9) 0.69510(12) 0.18860(6) 0.0344(4) Uani 1 1 d . . . H5Y H 0.3162 0.7525 0.1948 0.041 Uiso 1 1 calc R . . C6Y C 0.28168(10) 0.65934(12) 0.14313(6) 0.0400(4) Uani 1 1 d . . . H6Y H 0.3064 0.6926 0.1178 0.048 Uiso 1 1 calc R . . C7Y C 0.24004(10) 0.57545(13) 0.13428(6) 0.0396(4) Uani 1 1 d . . . H7Y H 0.2368 0.5517 0.1029 0.047 Uiso 1 1 calc R . . C8Y C 0.20296(9) 0.52550(12) 0.17038(5) 0.0328(4) Uani 1 1 d . . . H8Y H 0.1740 0.4684 0.1640 0.039 Uiso 1 1 calc R . . C9Y C 0.17240(8) 0.51990(10) 0.26099(5) 0.0242(3) Uani 1 1 d . . . C10Y C 0.08257(8) 0.51757(10) 0.25641(5) 0.0224(3) Uani 1 1 d . . . C11Y C 0.04097(8) 0.43240(11) 0.25304(5) 0.0272(4) Uani 1 1 d . . . H11Y H 0.0685 0.3729 0.2549 0.033 Uiso 1 1 calc R . . C12Y C 0.04043(8) 0.60328(10) 0.25317(5) 0.0295(4) Uani 1 1 d . . . H12Y H 0.0678 0.6628 0.2554 0.035 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 C1AX 0.0216(8) 0.0362(10) 0.0347(10) -0.0042(7) -0.0039(7) 0.0089(7) C4AX 0.0224(8) 0.0344(9) 0.0371(10) 0.0021(7) -0.0018(7) 0.0085(7) C5AX 0.0218(8) 0.0285(9) 0.0382(10) 0.0014(7) -0.0048(7) 0.0054(7) C8AX 0.0189(8) 0.0303(9) 0.0333(10) -0.0010(7) -0.0045(7) 0.0054(7) C1AY 0.0166(7) 0.0262(8) 0.0282(9) 0.0012(7) -0.0032(6) 0.0038(6) C4AY 0.0184(8) 0.0266(8) 0.0304(9) 0.0017(7) -0.0017(7) 0.0043(6) C5AY 0.0202(8) 0.0283(9) 0.0299(9) 0.0018(7) 0.0005(7) 0.0043(7) C8AY 0.0173(8) 0.0301(8) 0.0278(9) -0.0001(7) -0.0015(6) 0.0051(7) O1G1 0.0335(7) 0.0556(8) 0.0552(9) -0.0017(6) -0.0083(6) -0.0045(6) N1G1 0.0262(7) 0.0329(8) 0.0436(9) -0.0004(7) -0.0003(6) 0.0020(6) C1G1 0.0472(12) 0.0698(14) 0.0445(12) 0.0064(10) -0.0129(10) 0.0021(10) C2G1 0.0404(10) 0.0586(12) 0.0388(11) -0.0002(9) 0.0005(8) 0.0038(9) C3G1 0.0312(9) 0.0439(10) 0.0396(10) 0.0010(8) -0.0010(8) 0.0021(8) C4G1 0.0314(9) 0.0446(11) 0.0500(12) -0.0025(9) 0.0022(8) 0.0004(8) N1G2 0.0280(8) 0.0455(9) 0.0664(11) -0.0067(8) -0.0082(7) 0.0055(7) C2G2 0.0318(10) 0.0421(11) 0.0511(12) -0.0084(8) -0.0053(8) -0.0012(8) C3G2 0.0353(10) 0.0360(10) 0.0495(11) -0.0027(8) -0.0037(8) 0.0081(8) C4G2 0.0257(9) 0.0456(11) 0.0481(11) 0.0010(8) -0.0035(8) 0.0020(8) C5G2 0.0392(12) 0.0385(12) 0.135(2) 0.0018(12) -0.0221(12) -0.0042(9) C6G2 0.0413(12) 0.0374(11) 0.140(2) 0.0049(12) -0.0238(13) 0.0085(10) C7G2 0.0318(11) 0.0805(16) 0.0870(16) 0.0074(13) -0.0135(11) 0.0013(10) O1X 0.0230(6) 0.0277(6) 0.0628(8) -0.0001(5) -0.0042(5) 0.0029(5) C1X 0.0357(10) 0.0527(11) 0.0437(12) -0.0119(9) -0.0061(9) 0.0078(9) C2X 0.0532(12) 0.0764(15) 0.0340(12) -0.0102(10) -0.0010(10) 0.0225(11) C3X 0.0518(12) 0.0711(15) 0.0415(12) 0.0101(10) 0.0109(10) 0.0223(11) C4X 0.0350(10) 0.0471(11) 0.0477(12) 0.0092(9) 0.0046(9) 0.0080(8) C5X 0.0268(9) 0.0338(10) 0.0574(13) -0.0010(8) -0.0072(8) -0.0005(7) C6X 0.0362(10) 0.0417(11) 0.0542(13) -0.0139(9) -0.0169(9) 0.0050(9) C7X 0.0427(11) 0.0544(12) 0.0365(11) -0.0117(9) -0.0119(9) 0.0140(10) C8X 0.0315(9) 0.0417(10) 0.0359(10) 0.0008(8) -0.0013(8) 0.0046(8) C9X 0.0228(8) 0.0267(9) 0.0380(10) -0.0023(7) -0.0033(7) 0.0024(7) C10X 0.0239(8) 0.0283(8) 0.0328(9) -0.0050(7) -0.0037(7) 0.0006(7) C11X 0.0264(9) 0.0283(9) 0.0401(10) -0.0002(7) -0.0047(7) 0.0035(7) C12X 0.0240(8) 0.0285(9) 0.0431(10) 0.0002(7) -0.0005(7) -0.0021(7) O1Y 0.0238(6) 0.0247(6) 0.0438(7) 0.0017(5) -0.0060(5) 0.0039(5) C1Y 0.0263(8) 0.0317(9) 0.0314(10) 0.0041(7) -0.0010(7) 0.0020(7) C2Y 0.0337(9) 0.0414(10) 0.0275(9) -0.0029(8) -0.0040(7) 0.0047(8) C3Y 0.0310(9) 0.0325(9) 0.0368(11) -0.0061(7) -0.0071(8) 0.0009(7) C4Y 0.0266(9) 0.0269(9) 0.0399(11) -0.0002(7) -0.0033(7) -0.0014(7) C5Y 0.0296(9) 0.0343(9) 0.0394(11) 0.0031(8) 0.0044(7) -0.0020(7) C6Y 0.0379(10) 0.0480(11) 0.0341(11) 0.0066(8) 0.0070(8) -0.0023(8) C7Y 0.0342(9) 0.0558(12) 0.0287(10) -0.0020(8) 0.0017(8) 0.0025(9) C8Y 0.0259(9) 0.0386(10) 0.0340(10) -0.0037(8) -0.0004(7) -0.0002(7) C9Y 0.0201(8) 0.0242(8) 0.0283(9) 0.0020(6) -0.0018(6) 0.0021(6) C10Y 0.0203(8) 0.0274(8) 0.0195(8) 0.0005(6) -0.0003(6) 0.0011(6) C11Y 0.0244(8) 0.0247(8) 0.0325(9) 0.0016(7) -0.0008(7) 0.0025(6) C12Y 0.0238(8) 0.0240(8) 0.0407(10) 0.0008(7) -0.0025(7) -0.0030(6) _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 C1AX C1X 1.377(2) . ? C1AX C4AX 1.393(2) . ? C1AX C9X 1.532(2) . ? C4AX C4X 1.387(2) . ? C4AX C5AX 1.467(2) . ? C5AX C5X 1.389(2) . ? C5AX C8AX 1.397(2) . ? C8AX C8X 1.376(2) . ? C8AX C9X 1.536(2) . ? C1AY C1Y 1.376(2) . ? C1AY C4AY 1.400(2) . ? C1AY C9Y 1.528(2) . ? C4AY C4Y 1.388(2) . ? C4AY C5AY 1.474(2) . ? C5AY C5Y 1.391(2) . ? C5AY C8AY 1.399(2) . ? C8AY C8Y 1.381(2) . ? C8AY C9Y 1.529(2) . ? O1G1 C1G1 1.418(2) . ? O1G1 C4G1 1.4236(19) . ? N1G1 C3G1 1.459(2) . ? N1G1 C2G1 1.471(2) . ? N1G1 H1G1 0.948(9) . ? C1G1 C2G1 1.513(2) . ? C1G1 H1GB 0.9900 . ? C1G1 H1GA 0.9900 . ? C2G1 H2GB 0.9900 . ? C2G1 H2GA 0.9900 . ? C3G1 C4G1 1.508(2) . ? C3G1 H3GB 0.9900 . ? C3G1 H3GA 0.9900 . ? C4G1 H4GA 0.9900 . ? C4G1 H4GB 0.9900 . ? N1G2 C6G2 1.324(2) . ? N1G2 C2G2 1.325(2) . ? C2G2 C3G2 1.374(2) . ? C2G2 H2G2 0.9500 . ? C3G2 C4G2 1.369(2) . ? C3G2 H3G2 0.9500 . ? C4G2 C5G2 1.363(2) . ? C4G2 C7G2 1.502(2) . ? C5G2 C6G2 1.373(2) . ? C5G2 H4G2 0.9500 . ? C6G2 H5G2 0.9500 . ? C7G2 H7GA 0.9800 . ? C7G2 H7GC 0.9800 . ? C7G2 H7GB 0.9800 . ? O1X C9X 1.4236(17) . ? O1X H1OX 0.983(9) . ? C1X C2X 1.393(3) . ? C1X H1X 0.9500 . ? C2X C3X 1.376(3) . ? C2X H2X 0.9500 . ? C3X C4X 1.380(3) . ? C3X H3X 0.9500 . ? C4X H4X 0.9500 . ? C5X C6X 1.374(2) . ? C5X H5X 0.9500 . ? C6X C7X 1.377(2) . ? C6X H6X 0.9500 . ? C7X C8X 1.393(2) . ? C7X H7X 0.9500 . ? C8X H8X 0.9500 . ? C9X C10X 1.530(2) . ? C10X C11X 1.391(2) . ? C10X C12X 1.394(2) . ? C11X C12X 1.387(2) 7_566 ? C11X H11X 0.9500 . ? C12X C11X 1.387(2) 7_566 ? C12X H12X 0.9500 . ? O1Y C9Y 1.4261(16) . ? O1Y H1OY 0.980(9) . ? C1Y C2Y 1.392(2) . ? C1Y H1Y 0.9500 . ? C2Y C3Y 1.382(2) . ? C2Y H2Y 0.9500 . ? C3Y C4Y 1.387(2) . ? C3Y H3Y 0.9500 . ? C4Y H4Y 0.9500 . ? C5Y C6Y 1.384(2) . ? C5Y H5Y 0.9500 . ? C6Y C7Y 1.385(2) . ? C6Y H6Y 0.9500 . ? C7Y C8Y 1.387(2) . ? C7Y H7Y 0.9500 . ? C8Y H8Y 0.9500 . ? C9Y C10Y 1.5237(19) . ? C10Y C11Y 1.3800(19) . ? C10Y C12Y 1.3909(19) . ? C11Y C11Y 1.395(3) 2 ? C11Y H11Y 0.9500 . ? C12Y C12Y 1.378(3) 2 ? C12Y H12Y 0.9500 . ? 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 C1X C1AX C4AX 120.15(16) . . ? C1X C1AX C9X 128.90(15) . . ? C4AX C1AX C9X 110.94(13) . . ? C4X C4AX C1AX 120.98(15) . . ? C4X C4AX C5AX 130.22(16) . . ? C1AX C4AX C5AX 108.80(14) . . ? C5X C5AX C8AX 120.31(15) . . ? C5X C5AX C4AX 130.92(15) . . ? C8AX C5AX C4AX 108.78(13) . . ? C8X C8AX C5AX 120.62(14) . . ? C8X C8AX C9X 128.75(14) . . ? C5AX C8AX C9X 110.63(13) . . ? C1Y C1AY C4AY 120.67(13) . . ? C1Y C1AY C9Y 128.36(13) . . ? C4AY C1AY C9Y 110.92(13) . . ? C4Y C4AY C1AY 120.41(14) . . ? C4Y C4AY C5AY 131.04(14) . . ? C1AY C4AY C5AY 108.53(12) . . ? C5Y C5AY C8AY 120.39(14) . . ? C5Y C5AY C4AY 131.23(14) . . ? C8AY C5AY C4AY 108.39(12) . . ? C8Y C8AY C5AY 120.51(14) . . ? C8Y C8AY C9Y 128.42(14) . . ? C5AY C8AY C9Y 111.04(12) . . ? C1G1 O1G1 C4G1 110.37(13) . . ? C3G1 N1G1 C2G1 109.84(13) . . ? C3G1 N1G1 H1G1 110.5(11) . . ? C2G1 N1G1 H1G1 111.2(11) . . ? O1G1 C1G1 C2G1 111.17(14) . . ? O1G1 C1G1 H1GB 109.4 . . ? C2G1 C1G1 H1GB 109.4 . . ? O1G1 C1G1 H1GA 109.4 . . ? C2G1 C1G1 H1GA 109.4 . . ? H1GB C1G1 H1GA 108.0 . . ? N1G1 C2G1 C1G1 112.27(14) . . ? N1G1 C2G1 H2GB 109.1 . . ? C1G1 C2G1 H2GB 109.1 . . ? N1G1 C2G1 H2GA 109.1 . . ? C1G1 C2G1 H2GA 109.1 . . ? H2GB C2G1 H2GA 107.9 . . ? N1G1 C3G1 C4G1 113.22(13) . . ? N1G1 C3G1 H3GB 108.9 . . ? C4G1 C3G1 H3GB 108.9 . . ? N1G1 C3G1 H3GA 108.9 . . ? C4G1 C3G1 H3GA 108.9 . . ? H3GB C3G1 H3GA 107.7 . . ? O1G1 C4G1 C3G1 111.23(13) . . ? O1G1 C4G1 H4GA 109.4 . . ? C3G1 C4G1 H4GA 109.4 . . ? O1G1 C4G1 H4GB 109.4 . . ? C3G1 C4G1 H4GB 109.4 . . ? H4GA C4G1 H4GB 108.0 . . ? C6G2 N1G2 C2G2 115.39(14) . . ? N1G2 C2G2 C3G2 123.85(16) . . ? N1G2 C2G2 H2G2 118.1 . . ? C3G2 C2G2 H2G2 118.1 . . ? C4G2 C3G2 C2G2 120.30(15) . . ? C4G2 C3G2 H3G2 119.9 . . ? C2G2 C3G2 H3G2 119.9 . . ? C5G2 C4G2 C3G2 116.07(16) . . ? C5G2 C4G2 C7G2 121.71(17) . . ? C3G2 C4G2 C7G2 122.22(16) . . ? C4G2 C5G2 C6G2 120.31(18) . . ? C4G2 C5G2 H4G2 119.8 . . ? C6G2 C5G2 H4G2 119.8 . . ? N1G2 C6G2 C5G2 124.07(18) . . ? N1G2 C6G2 H5G2 118.0 . . ? C5G2 C6G2 H5G2 118.0 . . ? C4G2 C7G2 H7GA 109.5 . . ? C4G2 C7G2 H7GC 109.5 . . ? H7GA C7G2 H7GC 109.5 . . ? C4G2 C7G2 H7GB 109.5 . . ? H7GA C7G2 H7GB 109.5 . . ? H7GC C7G2 H7GB 109.5 . . ? C9X O1X H1OX 110.2(11) . . ? C1AX C1X C2X 118.54(18) . . ? C1AX C1X H1X 120.7 . . ? C2X C1X H1X 120.7 . . ? C3X C2X C1X 121.21(18) . . ? C3X C2X H2X 119.4 . . ? C1X C2X H2X 119.4 . . ? C2X C3X C4X 120.50(18) . . ? C2X C3X H3X 119.8 . . ? C4X C3X H3X 119.8 . . ? C3X C4X C4AX 118.61(18) . . ? C3X C4X H4X 120.7 . . ? C4AX C4X H4X 120.7 . . ? C6X C5X C5AX 118.68(16) . . ? C6X C5X H5X 120.7 . . ? C5AX C5X H5X 120.7 . . ? C5X C6X C7X 121.14(15) . . ? C5X C6X H6X 119.4 . . ? C7X C6X H6X 119.4 . . ? C6X C7X C8X 120.74(17) . . ? C6X C7X H7X 119.6 . . ? C8X C7X H7X 119.6 . . ? C8AX C8X C7X 118.52(16) . . ? C8AX C8X H8X 120.7 . . ? C7X C8X H8X 120.7 . . ? O1X C9X C10X 107.35(11) . . ? O1X C9X C1AX 112.63(12) . . ? C10X C9X C1AX 112.59(12) . . ? O1X C9X C8AX 112.54(12) . . ? C10X C9X C8AX 110.91(12) . . ? C1AX C9X C8AX 100.85(12) . . ? C11X C10X C12X 117.47(14) . . ? C11X C10X C9X 121.41(13) . . ? C12X C10X C9X 121.09(14) . . ? C12X C11X C10X 121.17(14) 7_566 . ? C12X C11X H11X 119.4 7_566 . ? C10X C11X H11X 119.4 . . ? C11X C12X C10X 121.36(14) 7_566 . ? C11X C12X H12X 119.3 7_566 . ? C10X C12X H12X 119.3 . . ? C9Y O1Y H1OY 105.1(11) . . ? C1AY C1Y C2Y 118.87(14) . . ? C1AY C1Y H1Y 120.6 . . ? C2Y C1Y H1Y 120.6 . . ? C3Y C2Y C1Y 120.44(15) . . ? C3Y C2Y H2Y 119.8 . . ? C1Y C2Y H2Y 119.8 . . ? C2Y C3Y C4Y 121.16(14) . . ? C2Y C3Y H3Y 119.4 . . ? C4Y C3Y H3Y 119.4 . . ? C3Y C4Y C4AY 118.41(14) . . ? C3Y C4Y H4Y 120.8 . . ? C4AY C4Y H4Y 120.8 . . ? C6Y C5Y C5AY 118.84(15) . . ? C6Y C5Y H5Y 120.6 . . ? C5AY C5Y H5Y 120.6 . . ? C5Y C6Y C7Y 120.40(15) . . ? C5Y C6Y H6Y 119.8 . . ? C7Y C6Y H6Y 119.8 . . ? C6Y C7Y C8Y 121.21(15) . . ? C6Y C7Y H7Y 119.4 . . ? C8Y C7Y H7Y 119.4 . . ? C8AY C8Y C7Y 118.65(15) . . ? C8AY C8Y H8Y 120.7 . . ? C7Y C8Y H8Y 120.7 . . ? O1Y C9Y C10Y 107.87(11) . . ? O1Y C9Y C1AY 111.78(11) . . ? C10Y C9Y C1AY 113.04(11) . . ? O1Y C9Y C8AY 113.16(11) . . ? C10Y C9Y C8AY 109.90(11) . . ? C1AY C9Y C8AY 101.09(11) . . ? C11Y C10Y C12Y 118.01(13) . . ? C11Y C10Y C9Y 122.10(12) . . ? C12Y C10Y C9Y 119.82(12) . . ? C10Y C11Y C11Y 120.92(8) . 2 ? C10Y C11Y H11Y 119.5 . . ? C11Y C11Y H11Y 119.5 2 . ? C12Y C12Y C10Y 121.07(8) 2 . ? C12Y C12Y H12Y 119.5 2 . ? C10Y C12Y H12Y 119.5 . . ? 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 C1X C1AX C4AX C4X 0.5(2) . . . . ? C9X C1AX C4AX C4X -179.40(13) . . . . ? C1X C1AX C4AX C5AX 179.46(13) . . . . ? C9X C1AX C4AX C5AX -0.43(16) . . . . ? C4X C4AX C5AX C5X -1.5(3) . . . . ? C1AX C4AX C5AX C5X 179.67(15) . . . . ? C4X C4AX C5AX C8AX 178.66(15) . . . . ? C1AX C4AX C5AX C8AX -0.19(16) . . . . ? C5X C5AX C8AX C8X 0.7(2) . . . . ? C4AX C5AX C8AX C8X -179.46(13) . . . . ? C5X C5AX C8AX C9X -179.15(13) . . . . ? C4AX C5AX C8AX C9X 0.73(16) . . . . ? C1Y C1AY C4AY C4Y -2.2(2) . . . . ? C9Y C1AY C4AY C4Y -179.72(12) . . . . ? C1Y C1AY C4AY C5AY 176.23(12) . . . . ? C9Y C1AY C4AY C5AY -1.26(15) . . . . ? C4Y C4AY C5AY C5Y -1.3(3) . . . . ? C1AY C4AY C5AY C5Y -179.56(14) . . . . ? C4Y C4AY C5AY C8AY 178.30(14) . . . . ? C1AY C4AY C5AY C8AY 0.07(15) . . . . ? C5Y C5AY C8AY C8Y -1.2(2) . . . . ? C4AY C5AY C8AY C8Y 179.16(12) . . . . ? C5Y C5AY C8AY C9Y -179.17(12) . . . . ? C4AY C5AY C8AY C9Y 1.15(15) . . . . ? C4G1 O1G1 C1G1 C2G1 59.26(19) . . . . ? C3G1 N1G1 C2G1 C1G1 50.55(19) . . . . ? O1G1 C1G1 C2G1 N1G1 -56.1(2) . . . . ? C2G1 N1G1 C3G1 C4G1 -50.21(18) . . . . ? C1G1 O1G1 C4G1 C3G1 -58.42(18) . . . . ? N1G1 C3G1 C4G1 O1G1 54.93(19) . . . . ? C6G2 N1G2 C2G2 C3G2 -1.5(3) . . . . ? N1G2 C2G2 C3G2 C4G2 0.6(3) . . . . ? C2G2 C3G2 C4G2 C5G2 0.2(3) . . . . ? C2G2 C3G2 C4G2 C7G2 179.55(17) . . . . ? C3G2 C4G2 C5G2 C6G2 -0.2(3) . . . . ? C7G2 C4G2 C5G2 C6G2 -179.5(2) . . . . ? C2G2 N1G2 C6G2 C5G2 1.6(3) . . . . ? C4G2 C5G2 C6G2 N1G2 -0.8(4) . . . . ? C4AX C1AX C1X C2X 0.8(2) . . . . ? C9X C1AX C1X C2X -179.38(14) . . . . ? C1AX C1X C2X C3X -1.0(3) . . . . ? C1X C2X C3X C4X 0.0(3) . . . . ? C2X C3X C4X C4AX 1.2(3) . . . . ? C1AX C4AX C4X C3X -1.5(2) . . . . ? C5AX C4AX C4X C3X 179.79(15) . . . . ? C8AX C5AX C5X C6X 0.0(2) . . . . ? C4AX C5AX C5X C6X -179.83(15) . . . . ? C5AX C5X C6X C7X -0.8(2) . . . . ? C5X C6X C7X C8X 1.0(2) . . . . ? C5AX C8AX C8X C7X -0.5(2) . . . . ? C9X C8AX C8X C7X 179.26(14) . . . . ? C6X C7X C8X C8AX -0.3(2) . . . . ? C1X C1AX C9X O1X -58.89(19) . . . . ? C4AX C1AX C9X O1X 120.98(13) . . . . ? C1X C1AX C9X C10X 62.7(2) . . . . ? C4AX C1AX C9X C10X -117.45(13) . . . . ? C1X C1AX C9X C8AX -179.07(15) . . . . ? C4AX C1AX C9X C8AX 0.80(15) . . . . ? C8X C8AX C9X O1X 59.05(19) . . . . ? C5AX C8AX C9X O1X -121.16(13) . . . . ? C8X C8AX C9X C10X -61.24(19) . . . . ? C5AX C8AX C9X C10X 118.55(13) . . . . ? C8X C8AX C9X C1AX 179.29(14) . . . . ? C5AX C8AX C9X C1AX -0.92(15) . . . . ? O1X C9X C10X C11X -16.07(19) . . . . ? C1AX C9X C10X C11X -140.58(15) . . . . ? C8AX C9X C10X C11X 107.26(16) . . . . ? O1X C9X C10X C12X 165.77(13) . . . . ? C1AX C9X C10X C12X 41.25(19) . . . . ? C8AX C9X C10X C12X -70.90(18) . . . . ? C12X C10X C11X C12X -0.2(2) . . . 7_566 ? C9X C10X C11X C12X -178.43(13) . . . 7_566 ? C11X C10X C12X C11X 0.2(2) . . . 7_566 ? C9X C10X C12X C11X 178.44(13) . . . 7_566 ? C4AY C1AY C1Y C2Y 0.6(2) . . . . ? C9Y C1AY C1Y C2Y 177.58(13) . . . . ? C1AY C1Y C2Y C3Y 1.4(2) . . . . ? C1Y C2Y C3Y C4Y -1.8(2) . . . . ? C2Y C3Y C4Y C4AY 0.1(2) . . . . ? C1AY C4AY C4Y C3Y 1.9(2) . . . . ? C5AY C4AY C4Y C3Y -176.20(14) . . . . ? C8AY C5AY C5Y C6Y 0.8(2) . . . . ? C4AY C5AY C5Y C6Y -179.65(14) . . . . ? C5AY C5Y C6Y C7Y -0.3(2) . . . . ? C5Y C6Y C7Y C8Y 0.3(2) . . . . ? C5AY C8AY C8Y C7Y 1.1(2) . . . . ? C9Y C8AY C8Y C7Y 178.72(13) . . . . ? C6Y C7Y C8Y C8AY -0.7(2) . . . . ? C1Y C1AY C9Y O1Y -54.76(19) . . . . ? C4AY C1AY C9Y O1Y 122.48(13) . . . . ? C1Y C1AY C9Y C10Y 67.17(18) . . . . ? C4AY C1AY C9Y C10Y -115.58(13) . . . . ? C1Y C1AY C9Y C8AY -175.43(13) . . . . ? C4AY C1AY C9Y C8AY 1.82(14) . . . . ? C8Y C8AY C9Y O1Y 60.73(18) . . . . ? C5AY C8AY C9Y O1Y -121.45(13) . . . . ? C8Y C8AY C9Y C10Y -59.92(18) . . . . ? C5AY C8AY C9Y C10Y 117.90(13) . . . . ? C8Y C8AY C9Y C1AY -179.59(14) . . . . ? C5AY C8AY C9Y C1AY -1.78(14) . . . . ? O1Y C9Y C10Y C11Y -12.89(18) . . . . ? C1AY C9Y C10Y C11Y -137.00(14) . . . . ? C8AY C9Y C10Y C11Y 110.90(15) . . . . ? O1Y C9Y C10Y C12Y 170.32(12) . . . . ? C1AY C9Y C10Y C12Y 46.22(18) . . . . ? C8AY C9Y C10Y C12Y -65.88(17) . . . . ? C12Y C10Y C11Y C11Y -0.5(3) . . . 2 ? C9Y C10Y C11Y C11Y -177.39(16) . . . 2 ? C11Y C10Y C12Y C12Y 0.1(3) . . . 2 ? C9Y C10Y C12Y C12Y 176.98(17) . . . 2 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1X H1OX N1G1 0.983(9) 1.752(10) 2.7299(16) 173.0(18) . O1Y H1OY N1G2 0.980(9) 1.824(10) 2.7980(17) 171.8(16) . N1G1 H1G1 O1X 0.948(9) 2.172(11) 3.0814(17) 160.6(16) 5_576 _diffrn_measured_fraction_theta_max 0.885 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.367 _refine_diff_density_min -0.391 _refine_diff_density_rms 0.108 # Attachment 'HMOR.CIF' data_hmor _database_code_depnum_ccdc_archive 'CCDC 817294' #TrackingRef 'HMOR.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1,4-bis(9-hydroxyfluoren-9-yl)benzene. morpholine clathrate' ; _chemical_name_common none _chemical_melting_point 264-265 _chemical_formula_moiety 'C32 H22 O2, 2(C4 H9 N O)' _chemical_formula_sum 'C40 H40 N2 O4' _chemical_formula_weight 612.74 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 triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.9644(3) _cell_length_b 9.5296(3) _cell_length_c 10.7651(4) _cell_angle_alpha 101.6810(10) _cell_angle_beta 91.685(2) _cell_angle_gamma 114.011(2) _cell_volume 816.21(5) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2429 _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 27.5 _exptl_crystal_description 'Clear plates' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.247 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 326 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type none _exptl_special_details ; Unstable without mother liquor under atmospheric conditions. Crystal coated with Paratone oil. ; _diffrn_ambient_temperature 173(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 Kappa CCD' _diffrn_measurement_method 'Combination of phi and omega' _diffrn_reflns_number 6823 _diffrn_reflns_av_R_equivalents 0.0320 _diffrn_reflns_av_sigmaI/netI 0.0625 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 27.51 _reflns_number_total 3669 _reflns_number_gt 2427 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 2000)' _computing_cell_refinement 'Collect (Nonius, 2000)' _computing_data_reduction 'Collect (Nonius, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSEED, graphical interface to SHELX (1999)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0536P)^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 none _refine_ls_number_reflns 3669 _refine_ls_number_parameters 216 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0815 _refine_ls_R_factor_gt 0.0424 _refine_ls_wR_factor_ref 0.1048 _refine_ls_wR_factor_gt 0.0932 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 0.22854(10) 0.11905(10) 0.05075(8) 0.0218(2) Uani 1 1 d D . . H1O H 0.1746(18) 0.0366(15) 0.0943(14) 0.050(5) Uiso 1 1 d D . . C1 C 0.15494(16) 0.35232(15) 0.26858(13) 0.0249(3) Uani 1 1 d . . . H1 H 0.0991 0.3564 0.1939 0.030 Uiso 1 1 calc R . . C2 C 0.11172(17) 0.39554(16) 0.38882(14) 0.0302(3) Uani 1 1 d . . . H2 H 0.0269 0.4312 0.3964 0.036 Uiso 1 1 calc R . . C3 C 0.19138(18) 0.38699(16) 0.49754(14) 0.0312(3) Uani 1 1 d . . . H3 H 0.1603 0.4165 0.5789 0.037 Uiso 1 1 calc R . . C4 C 0.31587(17) 0.33580(16) 0.48886(13) 0.0271(3) Uani 1 1 d . . . H4 H 0.3699 0.3296 0.5634 0.033 Uiso 1 1 calc R . . C5 C 0.59056(17) 0.19931(16) 0.40146(13) 0.0282(3) Uani 1 1 d . . . H5 H 0.5928 0.2148 0.4916 0.034 Uiso 1 1 calc R . . C6 C 0.69304(18) 0.14091(17) 0.33806(14) 0.0316(4) Uani 1 1 d . . . H6 H 0.7651 0.1147 0.3854 0.038 Uiso 1 1 calc R . . C7 C 0.69241(17) 0.12000(16) 0.20655(13) 0.0288(3) Uani 1 1 d . . . H7 H 0.7642 0.0804 0.1650 0.035 Uiso 1 1 calc R . . C8 C 0.58716(16) 0.15670(15) 0.13530(13) 0.0232(3) Uani 1 1 d . . . H8 H 0.5875 0.1441 0.0455 0.028 Uiso 1 1 calc R . . C9 C 0.35074(15) 0.25282(15) 0.14031(11) 0.0192(3) Uani 1 1 d . . . C10 C 0.42572(14) 0.38195(15) 0.06766(11) 0.0184(3) Uani 1 1 d . . . C11 C 0.43857(15) 0.34214(15) -0.06211(12) 0.0212(3) Uani 1 1 d . . . H11 H 0.3970 0.2340 -0.1058 0.025 Uiso 1 1 calc R . . C12 C 0.48843(15) 0.54119(15) 0.12843(12) 0.0214(3) Uani 1 1 d . . . H12 H 0.4813 0.5709 0.2170 0.026 Uiso 1 1 calc R . . C1A C 0.28041(15) 0.30346(15) 0.25982(12) 0.0196(3) Uani 1 1 d . . . C4A C 0.36016(15) 0.29386(15) 0.36932(12) 0.0206(3) Uani 1 1 d . . . C5A C 0.48434(15) 0.23483(15) 0.33034(12) 0.0207(3) Uani 1 1 d . . . C8A C 0.48197(15) 0.21190(14) 0.19765(12) 0.0192(3) Uani 1 1 d . . . O1G O 0.13228(12) -0.24945(12) 0.32550(9) 0.0355(3) Uani 1 1 d . . . N1G N 0.02067(14) -0.13784(13) 0.13293(11) 0.0257(3) Uani 1 1 d D . . H1G H -0.0659(16) -0.1512(19) 0.0705(13) 0.048(5) Uiso 1 1 d D . . C1G C 0.09744(18) -0.11494(17) 0.35754(13) 0.0303(3) Uani 1 1 d . . . H1GA H 0.1995 -0.0184 0.3621 0.036 Uiso 1 1 calc R . . H1GB H 0.0589 -0.1082 0.4429 0.036 Uiso 1 1 calc R . . C2G C -0.03202(17) -0.12252(17) 0.26070(13) 0.0288(3) Uani 1 1 d . . . H2GB H -0.1370 -0.2141 0.2608 0.035 Uiso 1 1 calc R . . H2GA H -0.0505 -0.0254 0.2838 0.035 Uiso 1 1 calc R . . C3G C 0.05790(19) -0.27618(17) 0.10123(14) 0.0348(4) Uani 1 1 d . . . H3GB H 0.0983 -0.2836 0.0166 0.042 Uiso 1 1 calc R . . H3GA H -0.0430 -0.3736 0.0972 0.042 Uiso 1 1 calc R . . C4G C 0.1873(2) -0.26024(19) 0.20228(15) 0.0389(4) Uani 1 1 d . . . H4GA H 0.2137 -0.3529 0.1810 0.047 Uiso 1 1 calc R . . H4GB H 0.2890 -0.1645 0.2038 0.047 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 0.0218(5) 0.0181(5) 0.0205(5) 0.0066(4) 0.0001(4) 0.0027(4) C1 0.0230(7) 0.0231(7) 0.0298(8) 0.0092(6) 0.0050(6) 0.0094(6) C2 0.0299(8) 0.0255(8) 0.0382(9) 0.0100(7) 0.0142(7) 0.0127(6) C3 0.0385(9) 0.0233(8) 0.0278(8) 0.0064(6) 0.0162(7) 0.0082(7) C4 0.0319(8) 0.0235(8) 0.0218(7) 0.0069(6) 0.0049(6) 0.0067(6) C5 0.0295(8) 0.0315(8) 0.0225(7) 0.0080(6) -0.0020(6) 0.0115(7) C6 0.0286(8) 0.0363(9) 0.0338(8) 0.0119(7) -0.0031(6) 0.0164(7) C7 0.0254(8) 0.0300(8) 0.0342(8) 0.0086(7) 0.0029(6) 0.0144(6) C8 0.0234(7) 0.0221(7) 0.0240(7) 0.0068(6) 0.0043(6) 0.0085(6) C9 0.0199(7) 0.0178(7) 0.0178(7) 0.0053(5) 0.0015(5) 0.0053(5) C10 0.0150(6) 0.0215(7) 0.0190(7) 0.0072(5) 0.0010(5) 0.0070(5) C11 0.0227(7) 0.0174(7) 0.0208(7) 0.0049(5) 0.0023(5) 0.0056(6) C12 0.0232(7) 0.0221(7) 0.0172(7) 0.0057(6) 0.0028(5) 0.0074(6) C1A 0.0193(7) 0.0159(7) 0.0205(7) 0.0065(5) 0.0034(5) 0.0034(5) C4A 0.0216(7) 0.0170(7) 0.0199(7) 0.0060(5) 0.0037(5) 0.0040(5) C5A 0.0200(7) 0.0192(7) 0.0196(7) 0.0066(5) 0.0011(5) 0.0041(5) C8A 0.0186(7) 0.0145(7) 0.0218(7) 0.0063(5) 0.0002(5) 0.0036(5) O1G 0.0380(6) 0.0379(6) 0.0403(6) 0.0239(5) 0.0063(5) 0.0188(5) N1G 0.0241(6) 0.0266(7) 0.0256(6) 0.0126(5) 0.0006(5) 0.0070(5) C1G 0.0310(8) 0.0281(8) 0.0297(8) 0.0121(6) 0.0017(6) 0.0081(6) C2G 0.0268(8) 0.0327(8) 0.0310(8) 0.0146(6) 0.0063(6) 0.0132(7) C3G 0.0408(9) 0.0267(8) 0.0346(9) 0.0089(7) 0.0093(7) 0.0111(7) C4G 0.0419(9) 0.0388(10) 0.0508(10) 0.0225(8) 0.0156(8) 0.0256(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 C9 1.4346(14) . ? O1 H1O 0.962(9) . ? C1 C1A 1.3804(18) . ? C1 C2 1.3924(19) . ? C1 H1 0.9500 . ? C2 C3 1.387(2) . ? C2 H2 0.9500 . ? C3 C4 1.387(2) . ? C3 H3 0.9500 . ? C4 C4A 1.3871(18) . ? C4 H4 0.9500 . ? C5 C6 1.385(2) . ? C5 C5A 1.3899(18) . ? C5 H5 0.9500 . ? C6 C7 1.3886(19) . ? C6 H6 0.9500 . ? C7 C8 1.3911(18) . ? C7 H7 0.9500 . ? C8 C8A 1.3835(18) . ? C8 H8 0.9500 . ? C9 C10 1.5248(17) . ? C9 C1A 1.5263(18) . ? C9 C8A 1.5314(17) . ? C10 C12 1.3888(18) . ? C10 C11 1.3925(17) . ? C11 C12 1.3896(17) 2_665 ? C11 H11 0.9500 . ? C12 C11 1.3896(18) 2_665 ? C12 H12 0.9500 . ? C1A C4A 1.3987(17) . ? C4A C5A 1.4742(19) . ? C5A C8A 1.3988(17) . ? O1G C1G 1.4187(17) . ? O1G C4G 1.4276(18) . ? N1G C3G 1.4658(18) . ? N1G C2G 1.4661(17) . ? N1G H1G 0.961(9) . ? C1G C2G 1.5063(18) . ? C1G H1GA 0.9900 . ? C1G H1GB 0.9900 . ? C2G H2GB 0.9900 . ? C2G H2GA 0.9900 . ? C3G C4G 1.506(2) . ? C3G H3GB 0.9900 . ? C3G H3GA 0.9900 . ? C4G H4GA 0.9900 . ? C4G H4GB 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 O1 H1O 108.9(10) . . ? C1A C1 C2 118.78(12) . . ? C1A C1 H1 120.6 . . ? C2 C1 H1 120.6 . . ? C3 C2 C1 120.57(13) . . ? C3 C2 H2 119.7 . . ? C1 C2 H2 119.7 . . ? C4 C3 C2 120.76(13) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 C4A 118.82(13) . . ? C3 C4 H4 120.6 . . ? C4A C4 H4 120.6 . . ? C6 C5 C5A 118.57(13) . . ? C6 C5 H5 120.7 . . ? C5A C5 H5 120.7 . . ? C5 C6 C7 121.19(13) . . ? C5 C6 H6 119.4 . . ? C7 C6 H6 119.4 . . ? C6 C7 C8 120.34(13) . . ? C6 C7 H7 119.8 . . ? C8 C7 H7 119.8 . . ? C8A C8 C7 118.77(12) . . ? C8A C8 H8 120.6 . . ? C7 C8 H8 120.6 . . ? O1 C9 C10 106.51(9) . . ? O1 C9 C1A 112.19(9) . . ? C10 C9 C1A 113.73(11) . . ? O1 C9 C8A 111.74(10) . . ? C10 C9 C8A 111.48(10) . . ? C1A C9 C8A 101.31(9) . . ? C12 C10 C11 118.03(11) . . ? C12 C10 C9 121.75(11) . . ? C11 C10 C9 120.18(11) . . ? C12 C11 C10 120.73(12) 2_665 . ? C12 C11 H11 119.6 2_665 . ? C10 C11 H11 119.6 . . ? C10 C12 C11 121.24(12) . 2_665 ? C10 C12 H12 119.4 . . ? C11 C12 H12 119.4 2_665 . ? C1 C1A C4A 120.68(12) . . ? C1 C1A C9 128.42(11) . . ? C4A C1A C9 110.90(11) . . ? C4 C4A C1A 120.36(12) . . ? C4 C4A C5A 131.13(12) . . ? C1A C4A C5A 108.50(11) . . ? C5 C5A C8A 120.32(13) . . ? C5 C5A C4A 131.05(12) . . ? C8A C5A C4A 108.61(11) . . ? C8 C8A C5A 120.78(12) . . ? C8 C8A C9 128.55(11) . . ? C5A C8A C9 110.66(11) . . ? C1G O1G C4G 109.60(10) . . ? C3G N1G C2G 109.96(11) . . ? C3G N1G H1G 108.6(10) . . ? C2G N1G H1G 109.8(10) . . ? O1G C1G C2G 111.53(11) . . ? O1G C1G H1GA 109.3 . . ? C2G C1G H1GA 109.3 . . ? O1G C1G H1GB 109.3 . . ? C2G C1G H1GB 109.3 . . ? H1GA C1G H1GB 108.0 . . ? N1G C2G C1G 110.07(11) . . ? N1G C2G H2GB 109.6 . . ? C1G C2G H2GB 109.6 . . ? N1G C2G H2GA 109.6 . . ? C1G C2G H2GA 109.6 . . ? H2GB C2G H2GA 108.2 . . ? N1G C3G C4G 109.01(12) . . ? N1G C3G H3GB 109.9 . . ? C4G C3G H3GB 109.9 . . ? N1G C3G H3GA 109.9 . . ? C4G C3G H3GA 109.9 . . ? H3GB C3G H3GA 108.3 . . ? O1G C4G C3G 111.14(12) . . ? O1G C4G H4GA 109.4 . . ? C3G C4G H4GA 109.4 . . ? O1G C4G H4GB 109.4 . . ? C3G C4G H4GB 109.4 . . ? H4GA C4G H4GB 108.0 . . ? 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 C1A C1 C2 C3 -1.1(2) . . . . ? C1 C2 C3 C4 0.2(2) . . . . ? C2 C3 C4 C4A 0.3(2) . . . . ? C5A C5 C6 C7 0.9(2) . . . . ? C5 C6 C7 C8 -0.4(2) . . . . ? C6 C7 C8 C8A -1.0(2) . . . . ? O1 C9 C10 C12 150.43(11) . . . . ? C1A C9 C10 C12 26.33(16) . . . . ? C8A C9 C10 C12 -87.44(14) . . . . ? O1 C9 C10 C11 -32.02(15) . . . . ? C1A C9 C10 C11 -156.12(11) . . . . ? C8A C9 C10 C11 90.11(13) . . . . ? C12 C10 C11 C12 -0.2(2) . . . 2_665 ? C9 C10 C11 C12 -177.86(11) . . . 2_665 ? C11 C10 C12 C11 0.2(2) . . . 2_665 ? C9 C10 C12 C11 177.83(11) . . . 2_665 ? C2 C1 C1A C4A 1.51(19) . . . . ? C2 C1 C1A C9 -179.13(12) . . . . ? O1 C9 C1A C1 -59.79(17) . . . . ? C10 C9 C1A C1 61.18(16) . . . . ? C8A C9 C1A C1 -179.10(12) . . . . ? O1 C9 C1A C4A 119.62(11) . . . . ? C10 C9 C1A C4A -119.41(11) . . . . ? C8A C9 C1A C4A 0.31(13) . . . . ? C3 C4 C4A C1A 0.09(19) . . . . ? C3 C4 C4A C5A -179.35(13) . . . . ? C1 C1A C4A C4 -1.01(19) . . . . ? C9 C1A C4A C4 179.52(11) . . . . ? C1 C1A C4A C5A 178.54(11) . . . . ? C9 C1A C4A C5A -0.92(14) . . . . ? C6 C5 C5A C8A -0.1(2) . . . . ? C6 C5 C5A C4A 178.32(13) . . . . ? C4 C4A C5A C5 2.2(2) . . . . ? C1A C4A C5A C5 -177.33(13) . . . . ? C4 C4A C5A C8A -179.30(13) . . . . ? C1A C4A C5A C8A 1.21(14) . . . . ? C7 C8 C8A C5A 1.81(19) . . . . ? C7 C8 C8A C9 -177.01(12) . . . . ? C5 C5A C8A C8 -1.31(19) . . . . ? C4A C5A C8A C8 179.97(11) . . . . ? C5 C5A C8A C9 177.70(11) . . . . ? C4A C5A C8A C9 -1.02(14) . . . . ? O1 C9 C8A C8 59.74(16) . . . . ? C10 C9 C8A C8 -59.32(16) . . . . ? C1A C9 C8A C8 179.37(12) . . . . ? O1 C9 C8A C5A -119.18(11) . . . . ? C10 C9 C8A C5A 121.77(12) . . . . ? C1A C9 C8A C5A 0.46(12) . . . . ? C4G O1G C1G C2G 58.76(15) . . . . ? C3G N1G C2G C1G 55.92(15) . . . . ? O1G C1G C2G N1G -57.14(15) . . . . ? C2G N1G C3G C4G -56.95(14) . . . . ? C1G O1G C4G C3G -60.25(15) . . . . ? N1G C3G C4G O1G 59.58(16) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1O N1G 0.962(9) 1.813(10) 2.7403(14) 161.1(14) . N1G H1G O1 0.961(9) 2.083(10) 3.0236(14) 165.7(14) 2 _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.182 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.044 # Attachment '- HPYR.CIF' data_hpyr _database_code_depnum_ccdc_archive 'CCDC 817295' #TrackingRef '- HPYR.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1,4-bis(9-hydroxyfluoren-9-yl)benzene. pyridine clathrate' ; _chemical_name_common "'1,4-bis(9-hydroxyfluoren-9-yl)benzene. pyridine clathrate'" _chemical_melting_point 264-265 _chemical_formula_moiety 'C32 H22 O2, 2(C5 H5 N)' _chemical_formula_sum 'C42 H32 N2 O2' _chemical_formula_weight 596.70 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 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.8538(3) _cell_length_b 10.4545(4) _cell_length_c 17.0843(8) _cell_angle_alpha 90.00 _cell_angle_beta 97.838(2) _cell_angle_gamma 90.00 _cell_volume 1566.58(11) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1763 _cell_measurement_theta_min 3.7 _cell_measurement_theta_max 25.7 _exptl_crystal_description 'Clear blocks' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.265 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 628 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type none _exptl_special_details ; Distance of O1-H1O is c=restrainted to 0.97(1) angstroms. ; _diffrn_ambient_temperature 173(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 Kappa CCD' _diffrn_measurement_method 'Combination of phi and omega' _diffrn_standards_number n/a _diffrn_standards_interval_count n/a _diffrn_standards_interval_time n/a _diffrn_standards_decay_% none _diffrn_reflns_number 5192 _diffrn_reflns_av_R_equivalents 0.0369 _diffrn_reflns_av_sigmaI/netI 0.0869 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.67 _diffrn_reflns_theta_max 25.67 _reflns_number_total 2945 _reflns_number_gt 1763 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 2000)' _computing_cell_refinement 'Collect (Nonius, 2000)' _computing_data_reduction 'Collect (Nonius, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSEED, graphical interface to SHELX (1999)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _publication_material ? _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^)+(0.0374P)^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 none _refine_ls_number_reflns 2945 _refine_ls_number_parameters 212 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0882 _refine_ls_R_factor_gt 0.0399 _refine_ls_wR_factor_ref 0.0935 _refine_ls_wR_factor_gt 0.0816 _refine_ls_goodness_of_fit_ref 0.899 _refine_ls_restrained_S_all 0.899 _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 0.70430(13) 0.39219(10) 0.10995(7) 0.0231(3) Uani 1 1 d D . . H1O H 0.629(2) 0.3383(17) 0.1301(13) 0.079(8) Uiso 1 1 d D . . C1 C 0.94286(19) 0.16678(15) 0.14149(10) 0.0247(4) Uani 1 1 d . . . H1 H 0.9881 0.2329 0.1750 0.030 Uiso 1 1 calc R . . C2 C 0.9842(2) 0.03936(16) 0.15608(11) 0.0286(4) Uani 1 1 d . . . H2 H 1.0579 0.0184 0.2000 0.034 Uiso 1 1 calc R . . C3 C 0.9184(2) -0.05724(16) 0.10687(11) 0.0308(5) Uani 1 1 d . . . H3 H 0.9480 -0.1436 0.1173 0.037 Uiso 1 1 calc R . . C4 C 0.81022(19) -0.02878(15) 0.04292(11) 0.0279(4) Uani 1 1 d . . . H4 H 0.7651 -0.0950 0.0095 0.034 Uiso 1 1 calc R . . C5 C 0.55821(19) 0.10133(17) -0.09428(11) 0.0280(4) Uani 1 1 d . . . H5 H 0.5591 0.0116 -0.1031 0.034 Uiso 1 1 calc R . . C6 C 0.45842(19) 0.17993(16) -0.14247(11) 0.0282(4) Uani 1 1 d . . . H6 H 0.3904 0.1436 -0.1844 0.034 Uiso 1 1 calc R . . C7 C 0.45752(18) 0.31110(16) -0.12981(11) 0.0263(4) Uani 1 1 d . . . H7 H 0.3884 0.3635 -0.1630 0.032 Uiso 1 1 calc R . . C8 C 0.55650(18) 0.36669(16) -0.06909(10) 0.0227(4) Uani 1 1 d . . . H8 H 0.5563 0.4566 -0.0609 0.027 Uiso 1 1 calc R . . C9 C 0.77220(17) 0.32559(14) 0.05028(10) 0.0191(4) Uani 1 1 d . . . C10 C 0.89250(18) 0.41555(14) 0.02532(10) 0.0187(4) Uani 1 1 d . . . C11 C 0.86096(18) 0.54555(14) 0.01610(9) 0.0201(4) Uani 1 1 d . . . H11 H 0.7657 0.5778 0.0271 0.024 Uiso 1 1 calc R . . C12 C 1.03319(18) 0.37148(15) 0.00887(10) 0.0211(4) Uani 1 1 d . . . H12 H 1.0570 0.2831 0.0149 0.025 Uiso 1 1 calc R . . C1A C 0.83509(18) 0.19520(15) 0.07757(10) 0.0196(4) Uani 1 1 d . . . C4A C 0.76831(18) 0.09817(15) 0.02814(10) 0.0214(4) Uani 1 1 d . . . C5A C 0.65616(18) 0.15587(15) -0.03327(10) 0.0212(4) Uani 1 1 d . . . C8A C 0.65525(18) 0.28858(15) -0.02083(10) 0.0196(4) Uani 1 1 d . . . N1G N 0.50563(16) 0.24377(13) 0.18434(9) 0.0282(4) Uani 1 1 d . . . C2G C 0.3714(2) 0.27664(17) 0.20612(12) 0.0325(5) Uani 1 1 d . . . H2G H 0.3157 0.3442 0.1784 0.039 Uiso 1 1 calc R . . C3G C 0.3094(2) 0.21732(18) 0.26700(11) 0.0332(5) Uani 1 1 d . . . H3G H 0.2143 0.2446 0.2811 0.040 Uiso 1 1 calc R . . C4G C 0.3886(2) 0.11815(17) 0.30658(11) 0.0318(5) Uani 1 1 d . . . H4G H 0.3486 0.0751 0.3482 0.038 Uiso 1 1 calc R . . C5G C 0.5266(2) 0.08243(16) 0.28480(11) 0.0308(5) Uani 1 1 d . . . H5G H 0.5836 0.0142 0.3110 0.037 Uiso 1 1 calc R . . C6G C 0.5803(2) 0.14760(16) 0.22437(10) 0.0282(4) Uani 1 1 d . . . H6G H 0.6762 0.1229 0.2102 0.034 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 0.0253(7) 0.0219(6) 0.0241(7) -0.0028(5) 0.0101(6) -0.0004(6) C1 0.0253(10) 0.0239(9) 0.0249(11) 0.0015(8) 0.0037(8) -0.0023(8) C2 0.0270(10) 0.0298(10) 0.0283(11) 0.0078(9) 0.0011(9) 0.0034(9) C3 0.0326(11) 0.0227(10) 0.0365(13) 0.0047(9) 0.0030(10) 0.0043(9) C4 0.0283(10) 0.0208(9) 0.0348(12) -0.0018(8) 0.0047(9) -0.0022(8) C5 0.0272(10) 0.0260(10) 0.0308(12) -0.0024(9) 0.0036(9) -0.0036(9) C6 0.0244(10) 0.0334(11) 0.0263(11) -0.0050(8) 0.0011(9) -0.0048(9) C7 0.0200(9) 0.0336(10) 0.0253(11) 0.0028(8) 0.0026(8) 0.0039(8) C8 0.0220(9) 0.0235(9) 0.0232(10) 0.0006(8) 0.0051(8) 0.0024(8) C9 0.0208(9) 0.0173(8) 0.0200(10) -0.0012(7) 0.0062(8) -0.0002(7) C10 0.0195(9) 0.0198(9) 0.0166(10) 0.0001(7) 0.0012(8) -0.0016(7) C11 0.0192(9) 0.0206(9) 0.0207(10) -0.0001(7) 0.0038(8) 0.0015(8) C12 0.0248(10) 0.0183(9) 0.0203(10) -0.0001(7) 0.0036(8) 0.0019(8) C1A 0.0191(9) 0.0194(9) 0.0215(10) 0.0027(7) 0.0071(8) -0.0012(7) C4A 0.0195(9) 0.0216(9) 0.0241(11) 0.0016(8) 0.0065(8) 0.0001(8) C5A 0.0194(9) 0.0231(9) 0.0222(10) 0.0003(8) 0.0061(8) -0.0014(8) C8A 0.0166(8) 0.0225(9) 0.0207(10) 0.0005(7) 0.0060(8) -0.0015(8) N1G 0.0276(9) 0.0284(9) 0.0292(10) 0.0014(7) 0.0063(7) -0.0031(7) C2G 0.0298(11) 0.0305(11) 0.0362(13) -0.0003(9) 0.0012(10) 0.0025(9) C3G 0.0212(10) 0.0481(12) 0.0309(12) -0.0069(10) 0.0057(9) -0.0037(9) C4G 0.0363(11) 0.0388(11) 0.0205(11) 0.0002(9) 0.0045(9) -0.0110(10) C5G 0.0373(11) 0.0300(11) 0.0241(12) -0.0004(8) 0.0012(9) -0.0001(9) C6G 0.0263(10) 0.0319(10) 0.0266(11) -0.0032(8) 0.0043(9) -0.0005(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 C9 1.4327(18) . ? O1 H1O 0.972(9) . ? C1 C1A 1.381(2) . ? C1 C2 1.395(2) . ? C1 H1 0.9500 . ? C2 C3 1.390(2) . ? C2 H2 0.9500 . ? C3 C4 1.384(2) . ? C3 H3 0.9500 . ? C4 C4A 1.392(2) . ? C4 H4 0.9500 . ? C5 C5A 1.385(2) . ? C5 C6 1.391(2) . ? C5 H5 0.9500 . ? C6 C7 1.388(2) . ? C6 H6 0.9500 . ? C7 C8 1.391(2) . ? C7 H7 0.9500 . ? C8 C8A 1.384(2) . ? C8 H8 0.9500 . ? C9 C1A 1.521(2) . ? C9 C10 1.525(2) . ? C9 C8A 1.535(2) . ? C10 C11 1.392(2) . ? C10 C12 1.392(2) . ? C11 C12 1.386(2) 3_765 ? C11 H11 0.9500 . ? C12 C11 1.386(2) 3_765 ? C12 H12 0.9500 . ? C1A C4A 1.398(2) . ? C4A C5A 1.472(2) . ? C5A C8A 1.404(2) . ? N1G C2G 1.337(2) . ? N1G C6G 1.339(2) . ? C2G C3G 1.387(3) . ? C2G H2G 0.9500 . ? C3G C4G 1.376(2) . ? C3G H3G 0.9500 . ? C4G C5G 1.377(2) . ? C4G H4G 0.9500 . ? C5G C6G 1.375(2) . ? C5G H5G 0.9500 . ? C6G H6G 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 O1 H1O 110.2(13) . . ? C1A C1 C2 118.88(16) . . ? C1A C1 H1 120.6 . . ? C2 C1 H1 120.6 . . ? C3 C2 C1 120.51(17) . . ? C3 C2 H2 119.7 . . ? C1 C2 H2 119.7 . . ? C4 C3 C2 120.61(16) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C3 C4 C4A 119.14(16) . . ? C3 C4 H4 120.4 . . ? C4A C4 H4 120.4 . . ? C5A C5 C6 118.97(16) . . ? C5A C5 H5 120.5 . . ? C6 C5 H5 120.5 . . ? C7 C6 C5 120.52(16) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C6 C7 C8 120.83(16) . . ? C6 C7 H7 119.6 . . ? C8 C7 H7 119.6 . . ? C8A C8 C7 118.72(16) . . ? C8A C8 H8 120.6 . . ? C7 C8 H8 120.6 . . ? O1 C9 C1A 112.89(13) . . ? O1 C9 C10 106.03(12) . . ? C1A C9 C10 113.45(12) . . ? O1 C9 C8A 112.49(12) . . ? C1A C9 C8A 101.30(12) . . ? C10 C9 C8A 110.84(13) . . ? C11 C10 C12 118.13(14) . . ? C11 C10 C9 119.79(13) . . ? C12 C10 C9 122.05(14) . . ? C12 C11 C10 120.80(14) 3_765 . ? C12 C11 H11 119.6 3_765 . ? C10 C11 H11 119.6 . . ? C11 C12 C10 121.07(14) 3_765 . ? C11 C12 H12 119.5 3_765 . ? C10 C12 H12 119.5 . . ? C1 C1A C4A 120.74(15) . . ? C1 C1A C9 128.29(15) . . ? C4A C1A C9 110.97(14) . . ? C4 C4A C1A 120.12(16) . . ? C4 C4A C5A 131.10(16) . . ? C1A C4A C5A 108.76(14) . . ? C5 C5A C8A 120.33(16) . . ? C5 C5A C4A 131.31(15) . . ? C8A C5A C4A 108.33(14) . . ? C8 C8A C5A 120.62(15) . . ? C8 C8A C9 128.78(14) . . ? C5A C8A C9 110.60(14) . . ? C2G N1G C6G 116.50(16) . . ? N1G C2G C3G 123.48(17) . . ? N1G C2G H2G 118.3 . . ? C3G C2G H2G 118.3 . . ? C4G C3G C2G 118.54(17) . . ? C4G C3G H3G 120.7 . . ? C2G C3G H3G 120.7 . . ? C3G C4G C5G 118.88(17) . . ? C3G C4G H4G 120.6 . . ? C5G C4G H4G 120.6 . . ? C6G C5G C4G 118.62(17) . . ? C6G C5G H5G 120.7 . . ? C4G C5G H5G 120.7 . . ? N1G C6G C5G 123.98(17) . . ? N1G C6G H6G 118.0 . . ? C5G C6G H6G 118.0 . . ? 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 C1A C1 C2 C3 0.3(2) . . . . ? C1 C2 C3 C4 -0.4(3) . . . . ? C2 C3 C4 C4A 0.3(3) . . . . ? C5A C5 C6 C7 0.3(3) . . . . ? C5 C6 C7 C8 0.3(3) . . . . ? C6 C7 C8 C8A -0.6(2) . . . . ? O1 C9 C10 C11 -41.12(19) . . . . ? C1A C9 C10 C11 -165.57(15) . . . . ? C8A C9 C10 C11 81.24(18) . . . . ? O1 C9 C10 C12 140.85(15) . . . . ? C1A C9 C10 C12 16.4(2) . . . . ? C8A C9 C10 C12 -96.79(18) . . . . ? C12 C10 C11 C12 0.1(3) . . . 3_765 ? C9 C10 C11 C12 -178.02(14) . . . 3_765 ? C11 C10 C12 C11 -0.1(3) . . . 3_765 ? C9 C10 C12 C11 177.97(15) . . . 3_765 ? C2 C1 C1A C4A 0.0(2) . . . . ? C2 C1 C1A C9 179.83(15) . . . . ? O1 C9 C1A C1 -57.6(2) . . . . ? C10 C9 C1A C1 63.0(2) . . . . ? C8A C9 C1A C1 -178.13(16) . . . . ? O1 C9 C1A C4A 122.26(14) . . . . ? C10 C9 C1A C4A -117.09(15) . . . . ? C8A C9 C1A C4A 1.74(16) . . . . ? C3 C4 C4A C1A 0.0(2) . . . . ? C3 C4 C4A C5A -178.52(17) . . . . ? C1 C1A C4A C4 -0.1(2) . . . . ? C9 C1A C4A C4 -179.97(14) . . . . ? C1 C1A C4A C5A 178.71(14) . . . . ? C9 C1A C4A C5A -1.17(18) . . . . ? C6 C5 C5A C8A -0.5(2) . . . . ? C6 C5 C5A C4A 177.43(16) . . . . ? C4 C4A C5A C5 0.5(3) . . . . ? C1A C4A C5A C5 -178.11(17) . . . . ? C4 C4A C5A C8A 178.62(17) . . . . ? C1A C4A C5A C8A 0.01(18) . . . . ? C7 C8 C8A C5A 0.4(2) . . . . ? C7 C8 C8A C9 -178.81(15) . . . . ? C5 C5A C8A C8 0.2(2) . . . . ? C4A C5A C8A C8 -178.21(14) . . . . ? C5 C5A C8A C9 179.51(14) . . . . ? C4A C5A C8A C9 1.15(18) . . . . ? O1 C9 C8A C8 56.8(2) . . . . ? C1A C9 C8A C8 177.56(16) . . . . ? C10 C9 C8A C8 -61.8(2) . . . . ? O1 C9 C8A C5A -122.53(14) . . . . ? C1A C9 C8A C5A -1.73(16) . . . . ? C10 C9 C8A C5A 118.96(14) . . . . ? C6G N1G C2G C3G 0.4(3) . . . . ? N1G C2G C3G C4G -0.9(3) . . . . ? C2G C3G C4G C5G 0.6(3) . . . . ? C3G C4G C5G C6G 0.2(3) . . . . ? C2G N1G C6G C5G 0.4(3) . . . . ? C4G C5G C6G N1G -0.7(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1O N1G 0.972(9) 1.817(10) 2.7797(17) 170(2) . _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.67 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.183 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.047