Electronic Supplementary Material for CrystEngComm This Journal is © The Royal SOciety of Chemistry 2004 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Prof Luigi R Nassimbeni' _publ_contact_author_address ; Department of Chemistry University of Cape Town Private Bag Rondebosch Cape Town 7701 SOUTH AFRICA ; _publ_contact_author_email XRAYLUIG@SCIENCE.UCT.AC.ZA _publ_section_title ; pH Control of Guest Selectivity by Inclusion ; loop_ _publ_author_name 'Luigi R. Nassimbeni' 'Susan A. Bourne' 'Kirsten C. Corin' 'Edwin Weber' data_H.An _database_code_depnum_ccdc_archive 'CCDC 222198' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,4-bis(9-hydroxyfluoren-9-yl)benzene. aniline clathrate ; _chemical_name_common '1,4-bis(9-hydroxyfluoren-9-yl)benzene. aniline clathrate' _chemical_melting_point 264-265 _chemical_formula_moiety 'C32 H22 O2. C6 H7 N' _chemical_formula_sum 'C38 H29 N O2' _chemical_formula_weight 531.62 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 P21/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 10.375(2) _cell_length_b 12.404(3) _cell_length_c 22.100(4) _cell_angle_alpha 90 _cell_angle_beta 90.46(3) _cell_angle_gamma 90 _cell_volume 2844.0(10) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5120 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25.4 _exptl_crystal_description 'Clear blocks' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.242 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type none _exptl_special_details ; Unstable without mother liquor under atmospheric conditions. Crystal coated with Paratone oil and data collected at 173K. ; _diffrn_ambient_temperature 293(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 8605 _diffrn_reflns_av_R_equivalents 0.0221 _diffrn_reflns_av_sigmaI/netI 0.0399 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 25.37 _reflns_number_total 5120 _reflns_number_gt 3728 _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, a 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^)+(0.0449P)^2^+1.0496P] 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 0.014(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5120 _refine_ls_number_parameters 373 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0755 _refine_ls_R_factor_gt 0.0492 _refine_ls_wR_factor_ref 0.1333 _refine_ls_wR_factor_gt 0.1189 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0.002 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 0.39805(14) 0.24836(11) 0.20365(6) 0.0566(4) Uani 1 1 d . . . H1O H 0.3244 0.2355 0.2147 0.068 Uiso 1 1 calc R . . O1' O 0.35869(14) -0.30047(11) 0.25697(6) 0.0530(4) Uani 1 1 d . . . H1'O H 0.3640 -0.3652 0.2640 0.064 Uiso 1 1 calc R . . C1'A C 0.29016(19) -0.33614(16) 0.15278(9) 0.0494(5) Uani 1 1 d . . . C14 C 0.41438(19) -0.08767(16) 0.23258(9) 0.0491(5) Uani 1 1 d . . . H14 H 0.4196 -0.1135 0.2720 0.059 Uiso 1 1 calc R . . C8'A C 0.51246(19) -0.33837(16) 0.17700(9) 0.0496(5) Uani 1 1 d . . . C9 C 0.42617(19) 0.18578(16) 0.15113(9) 0.0482(5) Uani 1 1 d . . . C13 C 0.39761(17) -0.15969(15) 0.18510(8) 0.0442(5) Uani 1 1 d . . . C10 C 0.41605(18) 0.06392(15) 0.16388(8) 0.0457(5) Uani 1 1 d . . . C11 C 0.40222(19) -0.00859(16) 0.11630(9) 0.0507(5) Uani 1 1 d . . . H11 H 0.3989 0.0170 0.0768 0.061 Uiso 1 1 calc R . . C9' C 0.38835(18) -0.28083(15) 0.19437(8) 0.0464(5) Uani 1 1 d . . . C8A C 0.34501(19) 0.21636(15) 0.09585(9) 0.0482(5) Uani 1 1 d . . . C5A C 0.4243(2) 0.24316(15) 0.04726(9) 0.0524(5) Uani 1 1 d . . . C1G C 0.9908(2) -0.03521(16) 0.17816(11) 0.0571(6) Uani 1 1 d . . . C15 C 0.42352(18) 0.02266(16) 0.22196(9) 0.0485(5) Uani 1 1 d . . . H15 H 0.4348 0.0694 0.2545 0.058 Uiso 1 1 calc R . . C4A C 0.5582(2) 0.24152(16) 0.06809(10) 0.0543(5) Uani 1 1 d . . . C12 C 0.39335(19) -0.11775(16) 0.12683(9) 0.0496(5) Uani 1 1 d . . . H12 H 0.3843 -0.1645 0.0942 0.060 Uiso 1 1 calc R . . C4'A C 0.3488(2) -0.41956(16) 0.12077(9) 0.0566(5) Uani 1 1 d . . . C1A C 0.56119(19) 0.21318(16) 0.12937(10) 0.0527(5) Uani 1 1 d . . . C8' C 0.6368(2) -0.31774(19) 0.19694(10) 0.0617(6) Uani 1 1 d . . . H8' H 0.6535 -0.2623 0.2242 0.074 Uiso 1 1 calc R . . C5'A C 0.4871(2) -0.42097(16) 0.13563(9) 0.0560(6) Uani 1 1 d . . . C5' C 0.5878(3) -0.48423(19) 0.11466(12) 0.0750(7) Uani 1 1 d . . . H5' H 0.5724 -0.5397 0.0872 0.090 Uiso 1 1 calc R . . C6G C 1.0039(2) -0.0221(2) 0.11646(11) 0.0703(7) Uani 1 1 d . . . H6G H 1.0853 -0.0116 0.1001 0.084 Uiso 1 1 calc R . . C5 C 0.3707(3) 0.26697(18) -0.00859(10) 0.0673(6) Uani 1 1 d . . . H5 H 0.4232 0.2840 -0.0412 0.081 Uiso 1 1 calc R . . C1' C 0.1611(2) -0.31347(18) 0.14456(10) 0.0596(6) Uani 1 1 d . . . H1' H 0.1224 -0.2571 0.1654 0.072 Uiso 1 1 calc R . . C4' C 0.2768(3) -0.4835(2) 0.08145(11) 0.0776(7) Uani 1 1 d . . . H4' H 0.3150 -0.5399 0.0605 0.093 Uiso 1 1 calc R . . C6' C 0.7114(3) -0.4632(2) 0.13529(13) 0.0807(8) Uani 1 1 d . . . H6' H 0.7793 -0.5053 0.1217 0.097 Uiso 1 1 calc R . . C8 C 0.2134(2) 0.21549(17) 0.08906(10) 0.0591(6) Uani 1 1 d . . . H8 H 0.1603 0.1987 0.1214 0.071 Uiso 1 1 calc R . . C2G C 0.8689(2) -0.05294(18) 0.20116(12) 0.0719(7) Uani 1 1 d . . . H2G H 0.8580 -0.0635 0.2425 0.086 Uiso 1 1 calc R . . C4 C 0.6717(2) 0.26794(18) 0.03878(12) 0.0694(7) Uani 1 1 d . . . H4 H 0.6710 0.2859 -0.0021 0.083 Uiso 1 1 calc R . . C1 C 0.6749(2) 0.21137(19) 0.16171(12) 0.0691(6) Uani 1 1 d . . . H1 H 0.6761 0.1918 0.2023 0.083 Uiso 1 1 calc R . . C7' C 0.7356(2) -0.3815(2) 0.17537(12) 0.0763(7) Uani 1 1 d . . . H7' H 0.8197 -0.3687 0.1883 0.092 Uiso 1 1 calc R . . C6 C 0.2385(3) 0.2652(2) -0.01542(11) 0.0759(7) Uani 1 1 d . . . H6 H 0.2016 0.2810 -0.0528 0.091 Uiso 1 1 calc R . . C3' C 0.1477(3) -0.4614(2) 0.07429(12) 0.0862(8) Uani 1 1 d . . . H3' H 0.0980 -0.5043 0.0486 0.103 Uiso 1 1 calc R . . C3 C 0.7858(3) 0.2670(2) 0.07139(15) 0.0852(8) Uani 1 1 d . . . H3 H 0.8623 0.2852 0.0523 0.102 Uiso 1 1 calc R . . C2' C 0.0902(3) -0.3768(2) 0.10444(12) 0.0764(7) Uani 1 1 d . . . H2' H 0.0034 -0.3620 0.0978 0.092 Uiso 1 1 calc R . . C3G C 0.7624(2) -0.0549(2) 0.16206(17) 0.0864(9) Uani 1 1 d . . . H3G H 0.6804 -0.0664 0.1775 0.104 Uiso 1 1 calc R . . C7 C 0.1614(2) 0.2403(2) 0.03258(11) 0.0709(7) Uani 1 1 d . . . H7 H 0.0723 0.2400 0.0273 0.085 Uiso 1 1 calc R . . C5G C 0.8972(3) -0.0245(3) 0.07902(13) 0.0924(9) Uani 1 1 d . . . H5G H 0.9071 -0.0152 0.0376 0.111 Uiso 1 1 calc R . . C2 C 0.7882(2) 0.2395(2) 0.13233(15) 0.0844(8) Uani 1 1 d . . . H2 H 0.8659 0.2398 0.1536 0.101 Uiso 1 1 calc R . . C4G C 0.7777(3) -0.0403(3) 0.10192(17) 0.1005(10) Uani 1 1 d . . . H4G H 0.7063 -0.0411 0.0762 0.121 Uiso 1 1 calc R . . N1G N 1.09866(18) -0.02583(15) 0.21702(9) 0.0673(5) Uani 1 1 d . . . H1GB H 1.1733 -0.0118 0.2023 0.081 Uiso 1 1 calc R . . H1GA H 1.0898 -0.0341 0.2554 0.081 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 0.0667(10) 0.0496(8) 0.0536(8) -0.0087(7) 0.0103(7) -0.0074(7) O1' 0.0652(9) 0.0482(8) 0.0457(8) 0.0079(6) 0.0095(6) 0.0039(7) C1'A 0.0580(13) 0.0422(11) 0.0480(11) 0.0079(9) 0.0023(9) -0.0042(9) C14 0.0547(12) 0.0510(12) 0.0416(10) 0.0040(9) 0.0010(9) -0.0001(10) C8'A 0.0553(13) 0.0438(11) 0.0498(11) 0.0073(9) 0.0089(9) 0.0032(9) C9 0.0536(12) 0.0440(11) 0.0471(11) -0.0026(9) 0.0052(9) -0.0026(9) C13 0.0436(10) 0.0441(11) 0.0450(11) 0.0008(9) 0.0042(8) 0.0028(8) C10 0.0474(11) 0.0444(11) 0.0455(11) -0.0002(9) 0.0049(8) -0.0021(9) C11 0.0653(13) 0.0455(12) 0.0412(11) 0.0039(9) 0.0064(9) -0.0020(10) C9' 0.0549(12) 0.0445(11) 0.0400(10) 0.0052(8) 0.0066(9) 0.0006(9) C8A 0.0544(12) 0.0375(10) 0.0528(12) -0.0005(9) 0.0056(9) 0.0027(9) C5A 0.0640(14) 0.0406(11) 0.0526(12) 0.0003(9) 0.0110(10) 0.0056(10) C1G 0.0573(13) 0.0394(11) 0.0747(15) -0.0135(10) 0.0074(11) -0.0018(10) C15 0.0537(12) 0.0468(12) 0.0452(11) -0.0049(9) 0.0022(9) -0.0030(9) C4A 0.0606(13) 0.0400(11) 0.0626(13) -0.0001(10) 0.0153(10) 0.0001(9) C12 0.0615(13) 0.0443(12) 0.0431(11) -0.0025(9) 0.0045(9) -0.0033(9) C4'A 0.0742(15) 0.0430(12) 0.0526(12) 0.0026(10) 0.0030(10) -0.0074(11) C1A 0.0533(13) 0.0423(11) 0.0625(13) -0.0021(10) 0.0055(10) -0.0044(9) C8' 0.0591(14) 0.0633(14) 0.0628(13) 0.0084(11) 0.0064(11) 0.0059(11) C5'A 0.0712(15) 0.0416(12) 0.0555(12) 0.0041(10) 0.0146(10) 0.0021(10) C5' 0.095(2) 0.0498(14) 0.0806(17) -0.0042(12) 0.0304(14) 0.0062(13) C6G 0.0636(15) 0.0695(16) 0.0780(17) -0.0158(13) 0.0105(13) -0.0097(12) C5 0.0894(18) 0.0599(14) 0.0526(13) 0.0061(11) 0.0135(12) 0.0141(13) C1' 0.0596(14) 0.0581(13) 0.0611(13) 0.0106(11) -0.0025(10) -0.0038(11) C4' 0.106(2) 0.0548(15) 0.0717(16) -0.0086(12) -0.0016(14) -0.0093(14) C6' 0.0761(18) 0.0676(17) 0.099(2) 0.0143(15) 0.0344(15) 0.0190(14) C8 0.0594(14) 0.0562(13) 0.0618(13) -0.0006(11) 0.0057(10) 0.0034(10) C2G 0.0685(16) 0.0512(14) 0.0963(18) -0.0058(13) 0.0241(14) -0.0012(12) C4 0.0705(16) 0.0580(14) 0.0803(16) -0.0001(12) 0.0279(13) 0.0003(12) C1 0.0600(15) 0.0622(15) 0.0851(17) 0.0027(13) -0.0054(13) -0.0101(12) C7' 0.0590(15) 0.0794(18) 0.0908(18) 0.0139(15) 0.0145(13) 0.0126(13) C6 0.092(2) 0.0759(17) 0.0596(15) 0.0037(13) -0.0062(13) 0.0220(14) C3' 0.104(2) 0.0705(18) 0.0835(19) -0.0033(15) -0.0226(16) -0.0223(17) C3 0.0598(17) 0.0736(18) 0.123(2) -0.0035(17) 0.0310(16) -0.0091(13) C2' 0.0717(16) 0.0783(18) 0.0788(17) 0.0179(15) -0.0163(13) -0.0134(14) C3G 0.0536(15) 0.0654(17) 0.140(3) -0.0195(18) 0.0154(17) -0.0096(12) C7 0.0629(15) 0.0747(16) 0.0749(16) -0.0042(13) -0.0086(12) 0.0150(12) C5G 0.090(2) 0.109(2) 0.0780(18) -0.0246(16) -0.0070(16) -0.0065(17) C2 0.0529(15) 0.0764(18) 0.124(3) -0.0012(17) 0.0011(15) -0.0083(13) C4G 0.075(2) 0.105(2) 0.121(3) -0.038(2) -0.0136(18) -0.0074(17) N1G 0.0612(12) 0.0670(13) 0.0737(12) -0.0106(10) 0.0037(10) 0.0002(10) _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 1.428(2) . ? O1' C9' 1.441(2) . ? C1'A C1' 1.378(3) . ? C1'A C4'A 1.396(3) . ? C1'A C9' 1.529(3) . ? C14 C13 1.388(3) . ? C14 C15 1.392(3) . ? C8'A C8' 1.383(3) . ? C8'A C5'A 1.397(3) . ? C8'A C9' 1.524(3) . ? C9 C1A 1.523(3) . ? C9 C8A 1.526(3) . ? C9 C10 1.541(3) . ? C13 C12 1.389(3) . ? C13 C9' 1.520(3) . ? C10 C15 1.383(3) . ? C10 C11 1.390(3) . ? C11 C12 1.377(3) . ? C8A C8 1.373(3) . ? C8A C5A 1.398(3) . ? C5A C5 1.382(3) . ? C5A C4A 1.460(3) . ? C1G C6G 1.381(3) . ? C1G C2G 1.384(3) . ? C1G N1G 1.410(3) . ? C4A C4 1.388(3) . ? C4A C1A 1.399(3) . ? C4'A C4' 1.390(3) . ? C4'A C5'A 1.470(3) . ? C1A C1 1.374(3) . ? C8' C7' 1.383(3) . ? C5'A C5' 1.389(3) . ? C5' C6' 1.382(4) . ? C6G C5G 1.377(4) . ? C5 C6 1.379(3) . ? C1' C2' 1.390(3) . ? C4' C3' 1.375(4) . ? C6' C7' 1.368(4) . ? C8 C7 1.390(3) . ? C2G C3G 1.398(4) . ? C4 C3 1.381(4) . ? C1 C2 1.392(3) . ? C6 C7 1.370(3) . ? C3' C2' 1.381(4) . ? C3 C2 1.390(4) . ? C3G C4G 1.352(4) . ? C5G C4G 1.357(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1' C1'A C4'A 120.7(2) . . ? C1' C1'A C9' 128.99(19) . . ? C4'A C1'A C9' 110.26(18) . . ? C13 C14 C15 120.90(18) . . ? C8' C8'A C5'A 120.95(19) . . ? C8' C8'A C9' 128.35(19) . . ? C5'A C8'A C9' 110.70(18) . . ? O1 C9 C1A 109.25(16) . . ? O1 C9 C8A 113.61(16) . . ? C1A C9 C8A 101.23(16) . . ? O1 C9 C10 111.69(15) . . ? C1A C9 C10 109.92(16) . . ? C8A C9 C10 110.62(16) . . ? C14 C13 C12 117.56(18) . . ? C14 C13 C9' 122.82(17) . . ? C12 C13 C9' 119.58(17) . . ? C15 C10 C11 117.85(18) . . ? C15 C10 C9 121.95(17) . . ? C11 C10 C9 120.19(17) . . ? C12 C11 C10 120.99(18) . . ? O1' C9' C13 108.11(15) . . ? O1' C9' C8'A 110.50(15) . . ? C13 C9' C8'A 112.00(15) . . ? O1' C9' C1'A 110.80(15) . . ? C13 C9' C1'A 113.89(16) . . ? C8'A C9' C1'A 101.46(16) . . ? C8 C8A C5A 120.6(2) . . ? C8 C8A C9 128.87(18) . . ? C5A C8A C9 110.47(18) . . ? C5 C5A C8A 120.2(2) . . ? C5 C5A C4A 131.3(2) . . ? C8A C5A C4A 108.59(18) . . ? C6G C1G C2G 118.6(2) . . ? C6G C1G N1G 120.5(2) . . ? C2G C1G N1G 120.8(2) . . ? C10 C15 C14 121.12(18) . . ? C4 C4A C1A 119.9(2) . . ? C4 C4A C5A 131.2(2) . . ? C1A C4A C5A 108.80(17) . . ? C11 C12 C13 121.54(19) . . ? C4' C4'A C1'A 120.4(2) . . ? C4' C4'A C5'A 130.7(2) . . ? C1'A C4'A C5'A 108.93(18) . . ? C1 C1A C4A 121.3(2) . . ? C1 C1A C9 128.3(2) . . ? C4A C1A C9 110.38(18) . . ? C8'A C8' C7' 118.4(2) . . ? C5' C5'A C8'A 119.6(2) . . ? C5' C5'A C4'A 131.9(2) . . ? C8'A C5'A C4'A 108.41(18) . . ? C6' C5' C5'A 118.8(2) . . ? C5G C6G C1G 120.4(2) . . ? C6 C5 C5A 119.1(2) . . ? C1'A C1' C2' 118.5(2) . . ? C3' C4' C4'A 118.5(2) . . ? C7' C6' C5' 121.2(2) . . ? C8A C8 C7 118.4(2) . . ? C1G C2G C3G 119.7(2) . . ? C3 C4 C4A 118.8(2) . . ? C1A C1 C2 118.5(2) . . ? C6' C7' C8' 121.0(2) . . ? C7 C6 C5 120.4(2) . . ? C4' C3' C2' 121.3(2) . . ? C4 C3 C2 121.1(2) . . ? C3' C2' C1' 120.6(2) . . ? C4G C3G C2G 120.5(3) . . ? C6 C7 C8 121.3(2) . . ? C4G C5G C6G 120.8(3) . . ? C3 C2 C1 120.4(3) . . ? C3G C4G C5G 120.1(3) . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 25.37 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.194 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.030 data_H_3Bz _database_code_depnum_ccdc_archive 'CCDC 222199' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common none _chemical_melting_point 264-265 _chemical_formula_moiety 'C32 H22 O2. 3(C7 H9 N)' _chemical_formula_sum 'C53 H49 N3 O2' _chemical_formula_weight 759.95 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 tetragonal _symmetry_space_group_name_H-M I-4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'y, -x, -z' '-x, -y, z' '-y, x, -z' 'x+1/2, y+1/2, z+1/2' 'y+1/2, -x+1/2, -z+1/2' '-x+1/2, -y+1/2, z+1/2' '-y+1/2, x+1/2, -z+1/2' _cell_length_a 22.524(3) _cell_length_b 22.524(3) _cell_length_c 16.721(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 8483(2) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 10097 _cell_measurement_theta_min 2.8 _cell_measurement_theta_max 27.9 _exptl_crystal_description 'clear blocks' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.190 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3232 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type none _exptl_special_details ; Unstable without mother liquor under atmospheric conditions for long periods of time. Crystal coated with Paratone oil and data collected at 173K. ; _diffrn_ambient_temperature 293(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 20087 _diffrn_reflns_av_R_equivalents 0.0318 _diffrn_reflns_av_sigmaI/netI 0.0446 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.75 _diffrn_reflns_theta_max 27.87 _reflns_number_total 10097 _reflns_number_gt 7306 _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, a 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^)+(0.0881P)^2^+1.4380P] 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 0.0009(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.8(15) _refine_ls_number_reflns 10097 _refine_ls_number_parameters 526 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0859 _refine_ls_R_factor_gt 0.0555 _refine_ls_wR_factor_ref 0.1568 _refine_ls_wR_factor_gt 0.1419 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _refine_ls_shift/su_max 0.063 _refine_ls_shift/su_mean 0.012 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 0.09249(7) 0.52957(7) 0.14806(10) 0.0361(4) Uani 1 1 d . . . H1 H 0.0607 0.5472 0.1453 0.043 Uiso 1 1 calc R . . C1 C 0.08821(15) 0.5739(2) -0.1499(2) 0.0797(11) Uani 1 1 d . . . H1A H 0.0787 0.5796 -0.2034 0.096 Uiso 1 1 calc R . . O2 O 0.40858(6) 0.47152(7) 0.09369(10) 0.0334(4) Uani 1 1 d . . . H2 H 0.4372 0.4492 0.0896 0.040 Uiso 1 1 calc R . . C2 C 0.42296(13) 0.50367(15) 0.35355(19) 0.0601(8) Uani 1 1 d . . . H2A H 0.4333 0.5383 0.3806 0.072 Uiso 1 1 calc R . . N3 N -0.05618(17) 0.63061(16) -0.1097(3) 0.1198(14) Uani 1 1 d . . . H3A H -0.0329 0.6282 -0.0691 0.144 Uiso 1 1 calc R . . H3B H -0.0780 0.6008 -0.1228 0.144 Uiso 1 1 calc R . . C3 C 0.36072(10) 0.38014(10) 0.14440(14) 0.0318(5) Uani 1 1 d . . . C4 C 0.20155(10) 0.48173(10) 0.16429(14) 0.0331(5) Uani 1 1 d . . . H4 H 0.1692 0.4674 0.1929 0.040 Uiso 1 1 calc R . . C5 C 0.14026(10) 0.62440(10) 0.10981(15) 0.0340(5) Uani 1 1 d . . . C6 C 0.29932(10) 0.52179(10) 0.07952(14) 0.0321(5) Uani 1 1 d . . . H6 H 0.3319 0.5355 0.0508 0.039 Uiso 1 1 calc R . . N7 N 0.51393(8) 0.41055(8) 0.09028(12) 0.0356(4) Uani 1 1 d . . . H7A H 0.5433 0.4204 0.0602 0.043 Uiso 1 1 calc R . . H7B H 0.4833 0.4333 0.0936 0.043 Uiso 1 1 calc R . . C7 C 0.42680(13) 0.45029(15) 0.39204(18) 0.0599(8) Uani 1 1 d . . . H7 H 0.4406 0.4490 0.4444 0.072 Uiso 1 1 calc R . . C8 C 0.30649(9) 0.47658(10) 0.13462(13) 0.0279(5) Uani 1 1 d . . . N9 N -0.01364(9) 0.58863(9) 0.16282(13) 0.0401(5) Uani 1 1 d . . . H9A H -0.0445 0.5781 0.1895 0.048 Uiso 1 1 calc R . . H9B H 0.0171 0.5661 0.1617 0.048 Uiso 1 1 calc R . . C9 C 0.08760(15) 0.5169(2) -0.1186(2) 0.0830(12) Uani 1 1 d . . . H9 H 0.0778 0.4850 -0.1514 0.100 Uiso 1 1 calc R . . C10 C 0.36725(9) 0.44745(9) 0.14961(14) 0.0288(5) Uani 1 1 d . . . C11 C 0.57134(10) 0.31802(11) 0.12661(14) 0.0372(5) Uani 1 1 d . . . C12 C 0.19403(9) 0.52716(9) 0.10959(13) 0.0269(5) Uani 1 1 d . . . C13 C 0.25749(10) 0.45750(10) 0.17648(14) 0.0358(5) Uani 1 1 d . . . H13 H 0.2620 0.4274 0.2141 0.043 Uiso 1 1 calc R . . C14 C 0.13447(10) 0.55739(10) 0.09685(14) 0.0314(5) Uani 1 1 d . . . C15 C 0.62750(11) 0.34068(12) 0.14135(16) 0.0427(6) Uani 1 1 d . . . H15 H 0.6314 0.3803 0.1562 0.051 Uiso 1 1 calc R . . C16 C -0.06967(10) 0.68136(12) 0.12493(15) 0.0396(6) Uani 1 1 d . . . C17 C 0.38762(10) 0.45538(11) 0.23614(14) 0.0341(5) Uani 1 1 d . . . C18 C -0.12380(11) 0.65895(13) 0.09993(18) 0.0479(6) Uani 1 1 d . . . H18 H -0.1260 0.6203 0.0804 0.057 Uiso 1 1 calc R . . C19 C 0.24381(10) 0.54684(10) 0.06682(14) 0.0335(5) Uani 1 1 d . . . H19 H 0.2396 0.5771 0.0294 0.040 Uiso 1 1 calc R . . C20 C -0.06788(12) 0.73842(13) 0.15445(18) 0.0510(7) Uani 1 1 d . . . H20 H -0.0320 0.7542 0.1722 0.061 Uiso 1 1 calc R . . C21 C 0.11583(10) 0.55517(12) 0.00880(15) 0.0402(6) Uani 1 1 d . . . C22 C 0.56705(12) 0.25898(12) 0.10452(19) 0.0544(7) Uani 1 1 d . . . H22 H 0.5300 0.2425 0.0943 0.065 Uiso 1 1 calc R . . C23 C 0.34424(11) 0.34601(11) 0.08009(18) 0.0424(6) Uani 1 1 d . . . H23 H 0.3367 0.3634 0.0307 0.051 Uiso 1 1 calc R . . C24 C 0.51604(11) 0.35545(11) 0.13563(16) 0.0425(6) Uani 1 1 d . . . H24A H 0.4822 0.3314 0.1202 0.051 Uiso 1 1 calc R . . H24B H 0.5114 0.3651 0.1918 0.051 Uiso 1 1 calc R . . C25 C -0.01345(11) 0.64509(12) 0.11913(18) 0.0476(7) Uani 1 1 d . . . H25A H -0.0058 0.6368 0.0631 0.057 Uiso 1 1 calc R . . H25B H 0.0193 0.6690 0.1388 0.057 Uiso 1 1 calc R . . C26 C 0.13837(13) 0.71725(14) 0.0368(3) 0.0672(10) Uani 1 1 d . . . H26 H 0.1334 0.7383 -0.0106 0.081 Uiso 1 1 calc R . . C27 C 0.15524(10) 0.65386(11) 0.17888(17) 0.0416(6) Uani 1 1 d . . . H27 H 0.1617 0.6332 0.2263 0.050 Uiso 1 1 calc R . . C28 C 0.10161(12) 0.50696(14) -0.03817(18) 0.0549(7) Uani 1 1 d . . . H28 H 0.1013 0.4688 -0.0170 0.066 Uiso 1 1 calc R . . C29 C 0.11628(10) 0.61270(12) -0.02401(16) 0.0440(6) Uani 1 1 d . . . C30 C 0.37290(10) 0.35387(11) 0.21907(16) 0.0369(6) Uani 1 1 d . . . C31 C 0.13179(11) 0.65519(12) 0.03874(18) 0.0435(6) Uani 1 1 d . . . C32 C 0.39101(10) 0.40124(11) 0.27528(15) 0.0370(5) Uani 1 1 d . . . C33 C -0.17206(14) 0.74988(15) 0.1326(3) 0.0726(10) Uani 1 1 d . . . H33 H -0.2063 0.7729 0.1352 0.087 Uiso 1 1 calc R . . C34 C 0.67734(12) 0.30633(13) 0.13465(19) 0.0526(7) Uani 1 1 d . . . H34 H 0.7145 0.3229 0.1437 0.063 Uiso 1 1 calc R . . C35 C 0.10231(14) 0.62121(19) -0.1042(2) 0.0704(10) Uani 1 1 d . . . H35 H 0.1027 0.6591 -0.1262 0.085 Uiso 1 1 calc R . . C36 C -0.11920(16) 0.77274(14) 0.1580(2) 0.0692(9) Uani 1 1 d . . . H36 H -0.1175 0.8113 0.1777 0.083 Uiso 1 1 calc R . . C37 C 0.40389(11) 0.50704(12) 0.27471(16) 0.0448(6) Uani 1 1 d . . . H37 H 0.4021 0.5434 0.2484 0.054 Uiso 1 1 calc R . . C38 C 0.36709(12) 0.29351(12) 0.2285(2) 0.0521(7) Uani 1 1 d . . . H38 H 0.3743 0.2761 0.2779 0.063 Uiso 1 1 calc R . . C39 C 0.16046(12) 0.71538(12) 0.1761(2) 0.0585(9) Uani 1 1 d . . . H39 H 0.1698 0.7360 0.2227 0.070 Uiso 1 1 calc R . . C40 C 0.35071(14) 0.25926(12) 0.1648(2) 0.0638(9) Uani 1 1 d . . . H40 H 0.3473 0.2184 0.1713 0.077 Uiso 1 1 calc R . . C41 C 0.33901(12) 0.28439(12) 0.0905(2) 0.0562(8) Uani 1 1 d . . . H41 H 0.3277 0.2604 0.0478 0.067 Uiso 1 1 calc R . . C42 C -0.02325(17) 0.75850(16) -0.0539(2) 0.0721(10) Uani 1 1 d . . . H42 H -0.0519 0.7443 -0.0188 0.087 Uiso 1 1 calc R . . C43 C -0.17485(12) 0.69350(14) 0.1036(2) 0.0604(8) Uani 1 1 d . . . H43 H -0.2109 0.6781 0.0862 0.073 Uiso 1 1 calc R . . C44 C 0.41049(12) 0.39807(14) 0.35429(17) 0.0525(7) Uani 1 1 d . . . H44 H 0.4125 0.3619 0.3809 0.063 Uiso 1 1 calc R . . C45 C 0.15230(14) 0.74613(13) 0.1069(3) 0.0674(10) Uani 1 1 d . . . H45 H 0.1562 0.7872 0.1070 0.081 Uiso 1 1 calc R . . C46 C 0.67259(14) 0.24711(14) 0.1145(2) 0.0693(10) Uani 1 1 d . . . H46 H 0.7061 0.2231 0.1124 0.083 Uiso 1 1 calc R . . C47 C 0.0564(2) 0.82539(18) -0.0796(3) 0.0885(13) Uani 1 1 d . . . H47 H 0.0818 0.8557 -0.0634 0.106 Uiso 1 1 calc R . . C48 C 0.02368(19) 0.75551(18) -0.1769(2) 0.0801(11) Uani 1 1 d . . . H48 H 0.0281 0.7395 -0.2278 0.096 Uiso 1 1 calc R . . C49 C -0.01907(17) 0.73355(14) -0.1276(2) 0.0709(9) Uani 1 1 d . . . C50 C 0.01332(18) 0.80417(15) -0.0288(2) 0.0772(10) Uani 1 1 d . . . H50 H 0.0088 0.8204 0.0220 0.093 Uiso 1 1 calc R . . C51 C 0.06111(17) 0.8017(2) -0.1524(3) 0.0918(13) Uani 1 1 d . . . H51 H 0.0897 0.8162 -0.1875 0.110 Uiso 1 1 calc R . . C52 C -0.0587(2) 0.68196(18) -0.1535(4) 0.125(2) Uani 1 1 d . . . H52A H -0.0995 0.6958 -0.1531 0.150 Uiso 1 1 calc R . . H52B H -0.0488 0.6723 -0.2084 0.150 Uiso 1 1 calc R . . C53 C 0.61736(15) 0.22427(14) 0.0975(3) 0.0759(11) Uani 1 1 d . . . H53 H 0.6138 0.1850 0.0811 0.091 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 0.0255(8) 0.0320(8) 0.0509(10) 0.0112(7) 0.0041(7) 0.0031(7) C1 0.061(2) 0.130(4) 0.0481(18) 0.011(2) -0.0148(16) 0.027(2) O2 0.0211(7) 0.0369(9) 0.0422(9) 0.0093(7) 0.0074(7) 0.0071(6) C2 0.0538(17) 0.071(2) 0.0557(17) -0.0151(14) -0.0168(14) 0.0041(14) N3 0.107(3) 0.078(2) 0.174(4) 0.019(3) -0.032(3) -0.017(2) C3 0.0227(11) 0.0284(11) 0.0442(13) 0.0045(10) 0.0071(10) 0.0085(9) C4 0.0254(11) 0.0314(12) 0.0424(13) 0.0072(10) 0.0077(10) 0.0017(9) C5 0.0221(11) 0.0291(11) 0.0507(15) 0.0050(11) 0.0062(10) 0.0058(9) C6 0.0269(11) 0.0292(11) 0.0402(13) 0.0075(10) 0.0034(9) 0.0042(9) N7 0.0262(10) 0.0370(11) 0.0435(11) 0.0026(9) 0.0055(9) 0.0056(8) C7 0.0522(16) 0.087(2) 0.0408(15) -0.0009(15) -0.0134(13) 0.0106(16) C8 0.0218(10) 0.0286(11) 0.0331(11) -0.0016(9) -0.0004(9) 0.0021(8) N9 0.0255(10) 0.0399(11) 0.0550(13) 0.0065(10) 0.0080(9) 0.0100(9) C9 0.058(2) 0.128(4) 0.063(2) -0.029(2) -0.0200(17) 0.018(2) C10 0.0222(11) 0.0277(11) 0.0366(12) 0.0054(9) 0.0026(9) 0.0055(8) C11 0.0343(13) 0.0387(13) 0.0386(13) 0.0039(10) -0.0007(10) 0.0059(10) C12 0.0245(10) 0.0235(10) 0.0328(11) -0.0011(9) -0.0012(9) 0.0038(8) C13 0.0325(12) 0.0352(12) 0.0396(13) 0.0142(10) 0.0065(11) 0.0080(10) C14 0.0244(11) 0.0319(11) 0.0379(12) 0.0048(10) 0.0012(9) 0.0006(9) C15 0.0357(13) 0.0427(14) 0.0497(15) -0.0061(12) 0.0015(11) 0.0038(11) C16 0.0300(12) 0.0435(14) 0.0453(14) 0.0104(12) 0.0035(10) 0.0042(11) C17 0.0212(10) 0.0420(13) 0.0392(12) 0.0061(10) 0.0008(9) 0.0083(9) C18 0.0360(13) 0.0506(15) 0.0570(16) -0.0020(13) -0.0031(12) 0.0016(11) C19 0.0269(11) 0.0326(12) 0.0408(13) 0.0112(10) 0.0031(10) 0.0045(9) C20 0.0414(15) 0.0531(16) 0.0587(17) 0.0057(14) -0.0041(13) -0.0001(13) C21 0.0261(11) 0.0539(15) 0.0406(13) 0.0019(12) -0.0033(10) 0.0103(10) C22 0.0427(15) 0.0407(15) 0.080(2) -0.0025(15) -0.0089(14) -0.0012(12) C23 0.0326(13) 0.0384(14) 0.0562(15) -0.0088(12) 0.0063(12) 0.0005(11) C24 0.0332(13) 0.0436(14) 0.0507(15) 0.0086(11) 0.0103(12) 0.0062(11) C25 0.0325(13) 0.0542(16) 0.0562(17) 0.0150(13) 0.0086(12) 0.0077(11) C26 0.0505(17) 0.0432(16) 0.108(3) 0.0347(19) 0.0237(18) 0.0179(13) C27 0.0294(12) 0.0383(14) 0.0572(16) -0.0028(12) 0.0082(12) 0.0049(10) C28 0.0424(14) 0.0679(19) 0.0544(16) -0.0117(14) -0.0116(12) 0.0076(13) C29 0.0259(11) 0.0561(16) 0.0501(15) 0.0186(12) 0.0045(10) 0.0133(10) C30 0.0255(11) 0.0356(12) 0.0495(14) 0.0107(10) 0.0044(10) 0.0086(9) C31 0.0287(12) 0.0405(13) 0.0614(16) 0.0184(12) 0.0122(11) 0.0121(10) C32 0.0266(11) 0.0446(13) 0.0396(12) 0.0097(10) 0.0011(9) 0.0069(9) C33 0.0503(19) 0.063(2) 0.105(3) -0.0020(19) -0.0065(19) 0.0281(16) C34 0.0343(14) 0.0602(17) 0.0633(17) 0.0001(14) -0.0072(13) 0.0064(12) C35 0.0498(17) 0.107(3) 0.0545(18) 0.029(2) -0.0005(14) 0.0304(18) C36 0.068(2) 0.0494(18) 0.090(2) -0.0093(18) -0.0022(19) 0.0147(16) C37 0.0405(13) 0.0454(14) 0.0486(14) -0.0034(11) -0.0075(11) 0.0055(11) C38 0.0429(14) 0.0362(14) 0.0772(19) 0.0201(14) 0.0047(14) 0.0043(11) C39 0.0421(15) 0.0334(14) 0.100(3) -0.0140(15) 0.0227(16) 0.0032(12) C40 0.0521(17) 0.0288(14) 0.110(3) 0.0107(17) 0.0151(18) 0.0037(12) C41 0.0401(14) 0.0346(15) 0.094(2) -0.0163(15) 0.0113(15) 0.0009(11) C42 0.078(2) 0.068(2) 0.070(2) 0.0310(18) -0.0042(17) 0.0031(17) C43 0.0334(14) 0.072(2) 0.076(2) -0.0034(17) -0.0130(14) 0.0081(13) C44 0.0403(14) 0.0711(19) 0.0460(15) 0.0161(14) -0.0032(12) 0.0127(13) C45 0.0525(17) 0.0284(14) 0.121(3) 0.0081(18) 0.0225(19) 0.0082(12) C46 0.0440(17) 0.058(2) 0.106(3) -0.0055(19) -0.0063(18) 0.0209(14) C47 0.097(3) 0.074(2) 0.094(3) 0.035(2) -0.043(2) -0.007(2) C48 0.097(3) 0.075(2) 0.068(2) 0.024(2) -0.007(2) 0.020(2) C49 0.094(3) 0.0514(17) 0.068(2) 0.0192(16) -0.0174(18) 0.0069(16) C50 0.098(3) 0.065(2) 0.069(2) 0.0103(17) -0.018(2) 0.0113(19) C51 0.074(2) 0.108(3) 0.093(3) 0.061(3) 0.002(2) 0.006(2) C52 0.148(4) 0.058(2) 0.169(5) 0.044(3) -0.077(4) -0.014(3) C53 0.060(2) 0.0427(17) 0.125(3) -0.016(2) -0.006(2) 0.0125(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C14 1.421(3) . ? C1 C35 1.349(6) . ? C1 C9 1.386(6) . ? O2 C10 1.427(3) . ? C2 C7 1.366(4) . ? C2 C37 1.389(4) . ? N3 C52 1.370(5) . ? C3 C23 1.373(4) . ? C3 C30 1.409(3) . ? C3 C10 1.526(3) . ? C4 C12 1.383(3) . ? C4 C13 1.388(3) . ? C5 C27 1.374(4) . ? C5 C31 1.389(3) . ? C5 C14 1.530(3) . ? C6 C8 1.383(3) . ? C6 C19 1.388(3) . ? N7 C24 1.455(3) . ? C7 C44 1.385(4) . ? C8 C13 1.376(3) . ? C8 C10 1.538(3) . ? N9 C25 1.467(3) . ? C9 C28 1.400(5) . ? C10 C17 1.528(3) . ? C11 C22 1.384(4) . ? C11 C15 1.386(4) . ? C11 C24 1.512(3) . ? C12 C19 1.402(3) . ? C12 C14 1.519(3) . ? C14 C21 1.532(3) . ? C15 C34 1.368(4) . ? C16 C20 1.377(4) . ? C16 C18 1.384(4) . ? C16 C25 1.510(3) . ? C17 C37 1.380(4) . ? C17 C32 1.386(3) . ? C18 C43 1.390(4) . ? C20 C36 1.392(4) . ? C21 C28 1.378(4) . ? C21 C29 1.407(4) . ? C22 C53 1.382(4) . ? C23 C41 1.404(4) . ? C26 C45 1.377(5) . ? C26 C31 1.406(4) . ? C27 C39 1.391(4) . ? C29 C35 1.391(4) . ? C29 C31 1.462(4) . ? C30 C38 1.375(4) . ? C30 C32 1.479(4) . ? C32 C44 1.394(4) . ? C33 C43 1.361(5) . ? C33 C36 1.365(5) . ? C34 C46 1.380(4) . ? C38 C40 1.365(5) . ? C39 C45 1.361(5) . ? C40 C41 1.391(5) . ? C42 C49 1.358(5) . ? C42 C50 1.383(5) . ? C46 C53 1.376(5) . ? C47 C51 1.334(6) . ? C47 C50 1.375(6) . ? C48 C49 1.361(5) . ? C48 C51 1.401(6) . ? C49 C52 1.527(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C35 C1 C9 121.4(3) . . ? C7 C2 C37 121.0(3) . . ? C23 C3 C30 120.8(2) . . ? C23 C3 C10 128.8(2) . . ? C30 C3 C10 110.4(2) . . ? C12 C4 C13 120.0(2) . . ? C27 C5 C31 120.8(2) . . ? C27 C5 C14 128.0(2) . . ? C31 C5 C14 111.1(2) . . ? C8 C6 C19 120.4(2) . . ? C2 C7 C44 121.1(3) . . ? C13 C8 C6 118.39(19) . . ? C13 C8 C10 119.8(2) . . ? C6 C8 C10 121.77(19) . . ? C1 C9 C28 120.5(4) . . ? O2 C10 C3 113.77(18) . . ? O2 C10 C17 112.35(18) . . ? C3 C10 C17 101.49(19) . . ? O2 C10 C8 108.15(17) . . ? C3 C10 C8 109.20(18) . . ? C17 C10 C8 111.81(18) . . ? C22 C11 C15 117.7(2) . . ? C22 C11 C24 120.3(2) . . ? C15 C11 C24 121.9(2) . . ? C4 C12 C19 118.25(19) . . ? C4 C12 C14 122.18(19) . . ? C19 C12 C14 119.53(19) . . ? C8 C13 C4 122.0(2) . . ? O1 C14 C12 107.78(17) . . ? O1 C14 C5 113.97(19) . . ? C12 C14 C5 110.30(18) . . ? O1 C14 C21 112.48(19) . . ? C12 C14 C21 111.23(19) . . ? C5 C14 C21 101.05(19) . . ? C34 C15 C11 121.8(2) . . ? C20 C16 C18 118.3(2) . . ? C20 C16 C25 120.2(2) . . ? C18 C16 C25 121.5(2) . . ? C37 C17 C32 120.4(2) . . ? C37 C17 C10 128.4(2) . . ? C32 C17 C10 111.1(2) . . ? C16 C18 C43 120.7(3) . . ? C6 C19 C12 120.9(2) . . ? C16 C20 C36 120.6(3) . . ? C28 C21 C29 120.3(2) . . ? C28 C21 C14 129.6(2) . . ? C29 C21 C14 110.0(2) . . ? C53 C22 C11 120.6(3) . . ? C3 C23 C41 118.6(3) . . ? N7 C24 C11 116.8(2) . . ? N9 C25 C16 115.8(2) . . ? C45 C26 C31 118.3(3) . . ? C5 C27 C39 118.3(3) . . ? C21 C28 C9 118.3(3) . . ? C35 C29 C21 120.1(3) . . ? C35 C29 C31 131.0(3) . . ? C21 C29 C31 108.9(2) . . ? C38 C30 C3 119.9(3) . . ? C38 C30 C32 131.8(3) . . ? C3 C30 C32 108.3(2) . . ? C5 C31 C26 120.1(3) . . ? C5 C31 C29 108.6(2) . . ? C26 C31 C29 131.3(3) . . ? C17 C32 C44 120.7(3) . . ? C17 C32 C30 108.6(2) . . ? C44 C32 C30 130.7(2) . . ? C43 C33 C36 120.2(3) . . ? C15 C34 C46 120.2(3) . . ? C1 C35 C29 119.3(3) . . ? C33 C36 C20 120.1(3) . . ? C17 C37 C2 118.7(3) . . ? C40 C38 C30 119.7(3) . . ? C45 C39 C27 121.6(3) . . ? C38 C40 C41 121.2(3) . . ? C40 C41 C23 119.8(3) . . ? C49 C42 C50 122.8(3) . . ? C33 C43 C18 120.0(3) . . ? C7 C44 C32 118.2(3) . . ? C39 C45 C26 120.9(3) . . ? C53 C46 C34 118.8(3) . . ? C51 C47 C50 118.8(4) . . ? C49 C48 C51 121.3(4) . . ? C42 C49 C48 116.6(4) . . ? C42 C49 C52 122.1(4) . . ? C48 C49 C52 121.2(4) . . ? C47 C50 C42 119.4(4) . . ? C47 C51 C48 121.0(4) . . ? N3 C52 C49 117.8(4) . . ? C46 C53 C22 120.8(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.520 _refine_diff_density_min -0.422 _refine_diff_density_rms 0.054