Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Menahem Kaftory' _publ_contact_author_address ; Schulich Faculty of Chemistry Technion Technion - Israel Institute of Tech Haifa 32000 ISRAEL ; _publ_contact_author_email KAFTORY@TX.TECHNION.AC.IL _publ_section_title ; Channels Formation through Photodimerization of Guest Molecules within Solid Inclusion Compounds ; loop_ _publ_author_name 'Menahem Kaftory' 'Tali Lavy' # Attachment '1-a(water diffused out).cif' data_hp1rest1 _database_code_depnum_ccdc_archive 'CCDC 603855' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,1,6,6-tetraphenyl-2,4-hexadiyne-1,6-diol 3,7-Diazatricyclo[4.2.2.22,5]dodeca-9,11-diene- 4,8-dione,2,6-dimethyl clathrate ; _chemical_name_common ; 1,1,6,6-tetraphenyl-2,4-hexadiyne-1,6-diol 3,7- Diazatricyclo(4.2.2.22,5)dodeca-9,11-diene-4,8-dione,2,6-dimethyl clathrate ; _chemical_melting_point ? _chemical_formula_moiety '(C30 H22 O2), (C12 H14 N2 O2)' _chemical_formula_sum 'C21 H18 N O2' _chemical_formula_weight 316.36 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 6.8620(3) _cell_length_b 10.2280(5) _cell_length_c 12.5800(6) _cell_angle_alpha 97.060(3) _cell_angle_beta 92.7230(19) _cell_angle_gamma 102.455(5) _cell_volume 853.11(7) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 113 _cell_measurement_theta_min 3.05 _cell_measurement_theta_max 24.66 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.232 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 334 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9691 _exptl_absorpt_correction_T_max 0.9921 _exptl_absorpt_process_details none _exptl_special_details ; ? ; _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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 4787 _diffrn_reflns_av_R_equivalents 0.0850 _diffrn_reflns_av_sigmaI/netI 0.2707 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 24.66 _reflns_number_total 1224 _reflns_number_gt 378 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_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^)+(0.0832P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1224 _refine_ls_number_parameters 180 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2706 _refine_ls_R_factor_gt 0.0763 _refine_ls_wR_factor_ref 0.2193 _refine_ls_wR_factor_gt 0.1555 _refine_ls_goodness_of_fit_ref 0.931 _refine_ls_restrained_S_all 0.931 _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 0.5041(16) 0.7799(14) 0.3166(7) 0.112(4) Uani 1 1 d . . . H1 H 0.53(2) 0.733(19) 0.364(11) 0.167 Uiso 1 1 d . . . C1 C 0.9290(18) 0.9747(15) 0.4569(10) 0.097(6) Uani 1 1 d . . . C2 C 0.811(2) 0.9336(18) 0.3791(13) 0.100(6) Uani 1 1 d . . . C3 C 0.667(2) 0.881(2) 0.2886(14) 0.096(5) Uani 1 1 d . . . C4 C 0.776(3) 0.809(2) 0.1959(13) 0.097(5) Uani 1 1 d . . . C5 C 0.669(2) 0.697(2) 0.1249(18) 0.126(7) Uani 1 1 d . . . H5 H 0.5277 0.6607 0.1250 0.151 Uiso 1 1 d R . . C6 C 0.772(4) 0.6441(19) 0.0431(13) 0.137(7) Uani 1 1 d . . . H6 H 0.7128 0.5639 -0.0055 0.165 Uiso 1 1 d R . . C7 C 0.963(3) 0.698(3) 0.0321(16) 0.131(8) Uani 1 1 d . . . H7 H 1.0238 0.6670 -0.0304 0.158 Uiso 1 1 d R . . C8 C 1.065(3) 0.804(3) 0.1026(19) 0.175(11) Uani 1 1 d . . . H8 H 1.2079 0.8288 0.0993 0.210 Uiso 1 1 d R . . C9 C 0.969(3) 0.862(2) 0.1829(13) 0.146(8) Uani 1 1 d . . . H9 H 1.0433 0.9421 0.2271 0.176 Uiso 1 1 d R . . C10 C 0.581(2) 0.993(2) 0.2555(15) 0.109(6) Uani 1 1 d . . . C11 C 0.454(2) 1.054(2) 0.3179(11) 0.104(5) Uani 1 1 d . . . H11 H 0.4451 0.9990 0.3745 0.125 Uiso 1 1 d R . . C12 C 0.377(2) 1.159(2) 0.288(2) 0.141(8) Uani 1 1 d . . . H12 H 0.3000 1.1974 0.3396 0.169 Uiso 1 1 d R . . C13 C 0.420(3) 1.208(2) 0.1906(18) 0.160(9) Uani 1 1 d . . . H13 H 0.3594 1.2835 0.1877 0.192 Uiso 1 1 d R . . C14 C 0.543(3) 1.149(2) 0.1284(13) 0.145(7) Uani 1 1 d . . . H14 H 0.5444 1.1785 0.0589 0.174 Uiso 1 1 d R . . C15 C 0.6237(18) 1.043(2) 0.1591(15) 0.116(6) Uani 1 1 d . . . H15 H 0.7145 1.0191 0.1081 0.139 Uiso 1 1 d R . . O2 O 0.3642(11) 0.4182(11) 0.5961(6) 0.113(3) Uiso 1 1 d . . . N1 N 0.2337(13) 0.4589(12) 0.4387(7) 0.092(3) Uiso 1 1 d . . . H1N1 H 0.3669 0.4774 0.4155 0.110 Uiso 1 1 d R . . C16 C 0.2186(17) 0.4228(16) 0.5334(11) 0.103(4) Uiso 1 1 d . . . C17 C 0.0061(17) 0.3838(16) 0.5748(9) 0.107(4) Uiso 1 1 d . . . H17 H 0.0009 0.3280 0.6311 0.129 Uiso 1 1 d R . . C18 C -0.1275(15) 0.3101(16) 0.4823(9) 0.093(4) Uiso 1 1 d . . . H18 H -0.2296 0.2343 0.4946 0.111 Uiso 1 1 d R . . C19 C -0.1153(16) 0.3484(17) 0.3873(9) 0.103(4) Uiso 1 1 d . . . H19 H -0.2046 0.2970 0.3285 0.124 Uiso 1 1 d R . . C20 C 0.0507(17) 0.4747(17) 0.3787(9) 0.099(4) Uiso 1 1 d . . . C21 C 0.1011(16) 0.4868(16) 0.2617(8) 0.124(5) Uiso 1 1 d . . . H21A H -0.0151 0.4948 0.2196 0.148 Uiso 1 1 d R . . H21B H 0.1430 0.4068 0.2331 0.148 Uiso 1 1 d R . . H21C H 0.2072 0.5646 0.2594 0.148 Uiso 1 1 d 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 0.096(7) 0.100(12) 0.138(10) 0.025(7) 0.006(6) 0.016(7) C1 0.104(17) 0.069(18) 0.124(18) 0.010(14) 0.012(10) 0.033(12) C2 0.108(14) 0.099(17) 0.092(13) 0.002(12) -0.003(9) 0.028(11) C3 0.092(12) 0.081(17) 0.111(13) 0.000(12) -0.013(12) 0.021(12) C4 0.114(14) 0.086(18) 0.100(13) 0.030(12) 0.003(12) 0.033(13) C5 0.128(14) 0.10(2) 0.134(15) -0.014(13) -0.024(14) 0.026(14) C6 0.19(2) 0.117(19) 0.102(14) -0.019(12) 0.006(14) 0.056(18) C7 0.090(14) 0.17(3) 0.151(18) 0.042(16) 0.020(13) 0.052(14) C8 0.089(14) 0.27(4) 0.143(18) -0.015(18) -0.009(13) 0.031(18) C9 0.100(15) 0.17(2) 0.156(16) -0.020(12) 0.047(12) 0.020(15) C10 0.114(13) 0.12(2) 0.101(15) 0.028(13) 0.011(10) 0.033(13) C11 0.088(11) 0.090(18) 0.124(12) 0.000(12) 0.022(10) 0.001(10) C12 0.143(14) 0.061(19) 0.23(3) 0.013(15) -0.011(14) 0.059(13) C13 0.20(2) 0.15(3) 0.146(19) 0.044(18) 0.011(14) 0.061(17) C14 0.170(17) 0.15(2) 0.128(15) 0.018(14) 0.004(13) 0.074(15) C15 0.106(11) 0.14(2) 0.133(15) 0.039(12) 0.014(10) 0.090(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 C3 1.443(18) . ? O1 H1 0.84(15) . ? C1 C2 1.212(14) . ? C1 C1 1.39(3) 2_776 ? C2 C3 1.438(16) . ? C3 C10 1.49(2) . ? C3 C4 1.600(19) . ? C4 C9 1.344(16) . ? C4 C5 1.407(17) . ? C5 C6 1.396(15) . ? C5 H5 0.9600 . ? C6 C7 1.324(18) . ? C6 H6 0.9600 . ? C7 C8 1.35(2) . ? C7 H7 0.9600 . ? C8 C9 1.379(17) . ? C8 H8 0.9600 . ? C9 H9 0.9600 . ? C10 C15 1.391(16) . ? C10 C11 1.399(17) . ? C11 C12 1.38(2) . ? C11 H11 0.9600 . ? C12 C13 1.392(19) . ? C12 H12 0.9600 . ? C13 C14 1.36(2) . ? C13 H13 0.9599 . ? C14 C15 1.41(2) . ? C14 H14 0.9600 . ? C15 H15 0.9600 . ? O2 C16 1.257(11) . ? N1 C16 1.292(12) . ? N1 C20 1.483(12) . ? N1 H1N1 0.9600 . ? C16 C17 1.558(14) . ? C17 C18 1.465(12) . ? C17 C20 1.627(18) 2_566 ? C17 H17 0.9601 . ? C18 C19 1.304(13) . ? C18 H18 0.9600 . ? C19 C20 1.545(18) . ? C19 H19 0.9600 . ? C20 C21 1.541(12) . ? C20 C17 1.627(18) 2_566 ? C21 H21A 0.9599 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 O1 H1 117(10) . . ? C2 C1 C1 177(2) . 2_776 ? C1 C2 C3 178.2(17) . . ? C2 C3 O1 110.9(14) . . ? C2 C3 C10 109.1(15) . . ? O1 C3 C10 107.4(13) . . ? C2 C3 C4 108.4(14) . . ? O1 C3 C4 107.2(15) . . ? C10 C3 C4 113.9(14) . . ? C9 C4 C5 119.9(16) . . ? C9 C4 C3 119(2) . . ? C5 C4 C3 121(2) . . ? C6 C5 C4 117.3(16) . . ? C6 C5 H5 118.5 . . ? C4 C5 H5 123.9 . . ? C7 C6 C5 121.6(19) . . ? C7 C6 H6 116.0 . . ? C5 C6 H6 122.3 . . ? C6 C7 C8 121(2) . . ? C6 C7 H7 119.3 . . ? C8 C7 H7 119.8 . . ? C7 C8 C9 120(2) . . ? C7 C8 H8 117.6 . . ? C9 C8 H8 122.1 . . ? C4 C9 C8 120.5(18) . . ? C4 C9 H9 121.9 . . ? C8 C9 H9 117.6 . . ? C15 C10 C11 115.9(17) . . ? C15 C10 C3 121.2(18) . . ? C11 C10 C3 122.9(18) . . ? C12 C11 C10 122.5(16) . . ? C12 C11 H11 139.4 . . ? C10 C11 H11 98.0 . . ? C11 C12 C13 121(2) . . ? C11 C12 H12 114.7 . . ? C13 C12 H12 124.1 . . ? C14 C13 C12 117(2) . . ? C14 C13 H13 135.2 . . ? C12 C13 H13 107.3 . . ? C13 C14 C15 122.2(19) . . ? C13 C14 H14 110.5 . . ? C15 C14 H14 126.4 . . ? C10 C15 C14 121.0(17) . . ? C10 C15 H15 128.6 . . ? C14 C15 H15 110.2 . . ? C16 N1 C20 118.5(10) . . ? C16 N1 H1N1 115.3 . . ? C20 N1 H1N1 126.1 . . ? O2 C16 N1 124.7(12) . . ? O2 C16 C17 116.8(12) . . ? N1 C16 C17 118.5(12) . . ? C18 C17 C16 106.5(10) . . ? C18 C17 C20 112.9(9) . 2_566 ? C16 C17 C20 106.1(12) . 2_566 ? C18 C17 H17 109.3 . . ? C16 C17 H17 113.1 . . ? C20 C17 H17 108.9 2_566 . ? C19 C18 C17 121.8(15) . . ? C19 C18 H18 120.5 . . ? C17 C18 H18 117.6 . . ? C18 C19 C20 115.6(13) . . ? C18 C19 H19 119.4 . . ? C20 C19 H19 125.0 . . ? N1 C20 C21 107.4(9) . . ? N1 C20 C19 107.1(13) . . ? C21 C20 C19 112.3(10) . . ? N1 C20 C17 110.1(10) . 2_566 ? C21 C20 C17 106.2(12) . 2_566 ? C19 C20 C17 113.6(10) . 2_566 ? C20 C21 H21A 109.9 . . ? C20 C21 H21B 108.3 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 110.2 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 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 C1 C1 C2 C3 159(41) 2_776 . . . ? C1 C2 C3 O1 13(50) . . . . ? C1 C2 C3 C10 131(49) . . . . ? C1 C2 C3 C4 -104(49) . . . . ? C2 C3 C4 C9 -35(2) . . . . ? O1 C3 C4 C9 -155.2(13) . . . . ? C10 C3 C4 C9 86.2(18) . . . . ? C2 C3 C4 C5 147.8(16) . . . . ? O1 C3 C4 C5 28(2) . . . . ? C10 C3 C4 C5 -91(2) . . . . ? C9 C4 C5 C6 0(2) . . . . ? C3 C4 C5 C6 177.0(14) . . . . ? C4 C5 C6 C7 0(2) . . . . ? C5 C6 C7 C8 2(3) . . . . ? C6 C7 C8 C9 -4(3) . . . . ? C5 C4 C9 C8 -2(2) . . . . ? C3 C4 C9 C8 -178.9(16) . . . . ? C7 C8 C9 C4 4(3) . . . . ? C2 C3 C10 C15 110.9(17) . . . . ? O1 C3 C10 C15 -128.9(15) . . . . ? C4 C3 C10 C15 -10(2) . . . . ? C2 C3 C10 C11 -69(2) . . . . ? O1 C3 C10 C11 51(2) . . . . ? C4 C3 C10 C11 169.5(15) . . . . ? C15 C10 C11 C12 -1(2) . . . . ? C3 C10 C11 C12 178.9(16) . . . . ? C10 C11 C12 C13 2(3) . . . . ? C11 C12 C13 C14 -1(3) . . . . ? C12 C13 C14 C15 0(3) . . . . ? C11 C10 C15 C14 0(2) . . . . ? C3 C10 C15 C14 -179.7(17) . . . . ? C13 C14 C15 C10 0(3) . . . . ? C20 N1 C16 O2 -173.1(14) . . . . ? C20 N1 C16 C17 6(2) . . . . ? O2 C16 C17 C18 -142.7(14) . . . . ? N1 C16 C17 C18 38.1(17) . . . . ? O2 C16 C17 C20 96.7(14) . . . 2_566 ? N1 C16 C17 C20 -82.4(15) . . . 2_566 ? C16 C17 C18 C19 -41.3(16) . . . . ? C20 C17 C18 C19 74.8(15) 2_566 . . . ? C17 C18 C19 C20 0.9(19) . . . . ? C16 N1 C20 C21 -167.8(13) . . . . ? C16 N1 C20 C19 -47.0(16) . . . . ? C16 N1 C20 C17 77.0(17) . . . 2_566 ? C18 C19 C20 N1 43.9(15) . . . . ? C18 C19 C20 C21 161.6(11) . . . . ? C18 C19 C20 C17 -77.9(15) . . . 2_566 ? _diffrn_measured_fraction_theta_max 0.426 _diffrn_reflns_theta_full 24.66 _diffrn_measured_fraction_theta_full 0.426 _refine_diff_density_max 0.174 _refine_diff_density_min -0.124 _refine_diff_density_rms 0.031 # Attachment '1-a.cif' data_hp1r4 _database_code_depnum_ccdc_archive 'CCDC 603856' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,1,6,6-tetraphenyl-2,4- hexadiyne-1,6-diol 3,7-Diazatricyclo[4.2.2.22,5]dodeca-9,11-diene- 4,8-dione,2,6-dimethyl clathrate monohydrate ; _chemical_name_common ; 1,1,6,6-tetraphenyl-2,4- hexadiyne-1,6-diol 3,7- Diazatricyclo(4.2.2.22,5)dodeca-9,11-diene-4,8-dione,2,6-dimethyl clathrate monohydrate ; _chemical_melting_point ? _chemical_formula_moiety '(C30 H22 O2), 2(C6 H7 N O)' _chemical_formula_sum 'C42 H38 N2 O5' _chemical_formula_weight 650.74 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' O O 0.0106 0.0060 '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' _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 10.864(3) _cell_length_b 11.536(3) _cell_length_c 16.320(6) _cell_angle_alpha 95.128(11) _cell_angle_beta 108.375(14) _cell_angle_gamma 112.176(15) _cell_volume 1746.2(9) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4191 _cell_measurement_theta_min 1.018 _cell_measurement_theta_max 27.485 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.238 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9683 _exptl_absorpt_correction_T_max 0.9919 _exptl_absorpt_process_details none _exptl_special_details ; ? ; _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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 8720 _diffrn_reflns_av_R_equivalents 0.0409 _diffrn_reflns_av_sigmaI/netI 0.2435 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.35 _diffrn_reflns_theta_max 25.10 _reflns_number_total 5431 _reflns_number_gt 1411 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_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^)+(0.0592P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5431 _refine_ls_number_parameters 458 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1765 _refine_ls_R_factor_gt 0.0387 _refine_ls_wR_factor_ref 0.1202 _refine_ls_wR_factor_gt 0.0814 _refine_ls_goodness_of_fit_ref 0.608 _refine_ls_restrained_S_all 0.608 _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 O1A O 0.5784(4) 0.1214(4) 0.4216(2) 0.0831(11) Uani 1 1 d . . . C1A C 0.7501(4) 0.2163(4) 0.2859(3) 0.0661(13) Uani 1 1 d . . . C2A C 0.7417(4) 0.1814(4) 0.3503(3) 0.0659(13) Uani 1 1 d . . . C3A C 0.7186(5) 0.1372(4) 0.4276(3) 0.0660(12) Uani 1 1 d . . . C4A C 0.7188(5) 0.0054(4) 0.4249(2) 0.0665(12) Uani 1 1 d . . . C5A C 0.6135(5) -0.0918(6) 0.4393(3) 0.0957(15) Uani 1 1 d . . . H5A H 0.5395 -0.0784 0.4490 0.115 Uiso 1 1 calc R . . C6A C 0.6176(6) -0.2117(6) 0.4392(4) 0.1203(19) Uani 1 1 d . . . H6A H 0.5477 -0.2771 0.4507 0.144 Uiso 1 1 calc R . . C7A C 0.7223(8) -0.2333(5) 0.4225(4) 0.123(2) Uani 1 1 d . . . H7A H 0.7222 -0.3142 0.4207 0.147 Uiso 1 1 calc R . . C8A C 0.8281(6) -0.1371(6) 0.4084(3) 0.1021(16) Uani 1 1 d . . . H8A H 0.9008 -0.1515 0.3975 0.123 Uiso 1 1 calc R . . C9A C 0.8261(5) -0.0178(5) 0.4103(3) 0.0820(14) Uani 1 1 d . . . H9A H 0.8991 0.0483 0.4016 0.098 Uiso 1 1 calc R . . C10A C 0.8317(5) 0.2299(5) 0.5138(3) 0.0695(13) Uani 1 1 d . . . C11A C 0.8127(5) 0.2114(5) 0.5920(4) 0.0951(16) Uani 1 1 d . . . H11A H 0.7303 0.1446 0.5912 0.114 Uiso 1 1 calc R . . C12A C 0.9178(7) 0.2938(6) 0.6724(3) 0.116(2) Uani 1 1 d . . . H12A H 0.9052 0.2824 0.7254 0.139 Uiso 1 1 calc R . . C13A C 1.0391(6) 0.3910(6) 0.6737(4) 0.113(2) Uani 1 1 d . . . H13A H 1.1094 0.4443 0.7278 0.135 Uiso 1 1 calc R . . C14A C 1.0588(6) 0.4113(5) 0.5976(4) 0.1065(18) Uani 1 1 d . . . H14A H 1.1411 0.4788 0.5990 0.128 Uiso 1 1 calc R . . C15A C 0.9533(6) 0.3290(5) 0.5168(3) 0.0864(15) Uani 1 1 d . . . H15A H 0.9661 0.3421 0.4641 0.104 Uiso 1 1 calc R . . C16A C 0.0485(5) 0.1269(4) 0.1216(3) 0.0687(12) Uani 1 1 d . . . C17A C 0.0875(4) 0.2140(4) 0.2102(3) 0.0746(13) Uani 1 1 d . . . H17A H 0.0034 0.2278 0.2089 0.090 Uiso 1 1 calc R . . C18A C 0.1226(5) 0.1469(5) 0.2829(3) 0.0933(16) Uani 1 1 d . . . H18A H 0.0869 0.1465 0.3278 0.112 Uiso 1 1 calc R . . C19A C 0.2041(5) 0.0895(4) 0.2813(3) 0.0899(15) Uani 1 1 d . . . H19A H 0.2303 0.0485 0.3258 0.108 Uiso 1 1 calc R . . C20A C 0.2554(4) 0.0905(4) 0.2061(3) 0.0778(13) Uani 1 1 d . . . C21A C 0.3074(4) -0.0144(4) 0.1938(3) 0.1150(18) Uani 1 1 d . . . H21A H 0.3382 -0.0090 0.1447 0.173 Uiso 1 1 calc R . . H21B H 0.2302 -0.0977 0.1822 0.173 Uiso 1 1 calc R . . H21C H 0.3862 -0.0020 0.2469 0.173 Uiso 1 1 calc R . . O2A O -0.0549(3) 0.1093(2) 0.05339(17) 0.0745(9) Uani 1 1 d . . . N1A N 0.1327(3) 0.0662(3) 0.1243(2) 0.0702(10) Uani 1 1 d . . . H1NA H 0.1148 0.0121 0.0775 0.084 Uiso 1 1 calc R . . O1B O 0.8780(3) 0.3213(3) 0.03903(18) 0.0734(9) Uani 1 1 d . . . C1B C 0.7555(4) 0.2547(4) 0.2081(3) 0.0653(13) Uani 1 1 d . . . C2B C 0.7562(4) 0.2847(4) 0.1407(3) 0.0623(12) Uani 1 1 d . . . C3B C 0.7596(4) 0.3265(4) 0.0576(3) 0.0594(11) Uani 1 1 d . . . C4B C 0.7832(5) 0.4665(4) 0.0697(2) 0.0614(11) Uani 1 1 d . . . C5B C 0.9049(5) 0.5632(5) 0.0695(2) 0.0676(12) Uani 1 1 d . . . H5B H 0.9758 0.5436 0.0604 0.081 Uiso 1 1 calc R . . C6B C 0.9229(4) 0.6900(5) 0.0828(2) 0.0780(13) Uani 1 1 d . . . H6B H 1.0053 0.7540 0.0813 0.094 Uiso 1 1 calc R . . C7B C 0.8226(6) 0.7227(5) 0.0979(3) 0.0899(15) Uani 1 1 d . . . H7B H 0.8369 0.8083 0.1076 0.108 Uiso 1 1 calc R . . C8B C 0.7007(5) 0.6278(5) 0.0985(3) 0.0938(16) Uani 1 1 d . . . H8B H 0.6312 0.6487 0.1086 0.113 Uiso 1 1 calc R . . C9B C 0.6805(4) 0.5008(4) 0.0841(3) 0.0818(13) Uani 1 1 d . . . H9B H 0.5966 0.4370 0.0840 0.098 Uiso 1 1 calc R . . C10B C 0.6196(5) 0.2434(4) -0.0236(3) 0.0649(12) Uani 1 1 d . . . C11B C 0.6095(5) 0.2625(4) -0.1071(3) 0.0833(14) Uani 1 1 d . . . H11B H 0.6881 0.3240 -0.1141 0.100 Uiso 1 1 calc R . . C12B C 0.4827(6) 0.1910(5) -0.1816(3) 0.0985(17) Uani 1 1 d . . . H12B H 0.4768 0.2046 -0.2377 0.118 Uiso 1 1 calc R . . C13B C 0.3680(6) 0.1007(6) -0.1704(4) 0.104(2) Uani 1 1 d . . . H13B H 0.2834 0.0532 -0.2196 0.124 Uiso 1 1 calc R . . C14B C 0.3747(5) 0.0789(4) -0.0891(4) 0.0931(16) Uani 1 1 d . . . H14B H 0.2956 0.0169 -0.0829 0.112 Uiso 1 1 calc R . . C15B C 0.5021(5) 0.1506(4) -0.0142(3) 0.0763(13) Uani 1 1 d . . . H15B H 0.5074 0.1357 0.0416 0.092 Uiso 1 1 calc R . . O2B O 0.5237(3) 0.3283(3) 0.3780(2) 0.0921(10) Uani 1 1 d . . . N1B N 0.3405(3) 0.3771(3) 0.3077(2) 0.0790(11) Uani 1 1 d . . . H1NB H 0.3600 0.4326 0.3542 0.095 Uiso 1 1 calc . . . C16B C 0.4225(5) 0.3154(4) 0.3106(3) 0.0718(13) Uani 1 1 d . . . C17B C 0.3865(4) 0.2286(4) 0.2227(3) 0.0753(13) Uani 1 1 d . . . H17B H 0.4712 0.2152 0.2245 0.090 Uiso 1 1 calc R . . C18B C 0.3507(4) 0.2948(4) 0.1506(3) 0.0845(14) Uani 1 1 d . . . H18B H 0.3858 0.2948 0.1055 0.101 Uiso 1 1 calc R . . C19B C 0.2681(5) 0.3534(4) 0.1523(3) 0.0841(15) Uani 1 1 d . . . H19B H 0.2419 0.3944 0.1078 0.101 Uiso 1 1 calc R . . C20B C 0.2179(5) 0.3523(4) 0.2272(3) 0.0738(13) Uani 1 1 d . . . C21B C 0.1705(4) 0.4599(4) 0.2395(3) 0.1128(18) Uani 1 1 d . . . H21D H 0.1394 0.4559 0.2885 0.169 Uiso 1 1 calc R . . H21E H 0.0927 0.4492 0.1864 0.169 Uiso 1 1 calc R . . H21F H 0.2497 0.5420 0.2514 0.169 Uiso 1 1 calc R . . O1W O 0.3028(4) 0.5087(5) 0.4574(2) 0.1392(15) Uani 1 1 d . . . H1OA H 0.580(5) 0.187(4) 0.421(3) 0.08(2) Uiso 1 1 d . . . H1OB H 0.884(4) 0.252(3) 0.049(2) 0.088(17) Uiso 1 1 d . . . H1WA H 0.354(5) 0.457(5) 0.472(3) 0.15(3) Uiso 1 1 d . . . H1WB H 0.381(7) 0.584(7) 0.522(5) 0.29(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1A 0.080(3) 0.096(3) 0.089(2) 0.029(2) 0.0375(17) 0.048(2) C1A 0.069(3) 0.066(3) 0.058(3) 0.013(3) 0.014(3) 0.032(3) C2A 0.071(3) 0.062(3) 0.058(3) 0.020(3) 0.013(3) 0.030(2) C3A 0.075(3) 0.080(4) 0.055(3) 0.027(3) 0.028(3) 0.040(3) C4A 0.075(3) 0.067(4) 0.059(3) 0.017(3) 0.025(2) 0.032(3) C5A 0.110(4) 0.085(4) 0.118(4) 0.035(3) 0.067(3) 0.047(4) C6A 0.140(5) 0.097(5) 0.151(5) 0.047(4) 0.087(4) 0.047(4) C7A 0.161(6) 0.076(5) 0.146(5) 0.039(4) 0.067(5) 0.056(5) C8A 0.110(5) 0.099(4) 0.115(4) 0.025(4) 0.041(3) 0.064(4) C9A 0.085(3) 0.084(4) 0.087(3) 0.019(3) 0.034(3) 0.046(3) C10A 0.076(3) 0.075(4) 0.060(3) 0.018(3) 0.022(3) 0.039(3) C11A 0.121(4) 0.113(4) 0.065(3) 0.027(4) 0.040(4) 0.058(4) C12A 0.166(6) 0.136(6) 0.056(4) 0.016(4) 0.032(4) 0.085(5) C13A 0.119(5) 0.090(5) 0.088(5) -0.007(4) -0.002(4) 0.042(4) C14A 0.134(5) 0.088(4) 0.088(4) 0.020(4) 0.030(4) 0.048(4) C15A 0.102(4) 0.087(4) 0.056(3) 0.002(3) 0.012(3) 0.045(3) C16A 0.068(3) 0.064(3) 0.074(4) 0.019(3) 0.029(3) 0.025(3) C17A 0.063(3) 0.094(4) 0.070(3) 0.006(3) 0.025(3) 0.039(3) C18A 0.083(4) 0.114(4) 0.081(4) 0.023(3) 0.034(3) 0.037(3) C19A 0.095(4) 0.093(4) 0.067(4) 0.023(3) 0.022(3) 0.031(3) C20A 0.068(3) 0.068(3) 0.081(3) 0.007(3) 0.001(3) 0.037(3) C21A 0.108(4) 0.085(4) 0.124(4) -0.009(3) -0.010(3) 0.064(3) O2A 0.0658(18) 0.079(2) 0.0728(19) 0.0098(17) 0.0129(16) 0.0376(17) N1A 0.063(2) 0.062(2) 0.071(2) -0.0013(19) 0.009(2) 0.029(2) O1B 0.074(2) 0.083(3) 0.084(2) 0.0294(19) 0.0382(16) 0.0458(19) C1B 0.066(3) 0.067(3) 0.061(3) 0.011(3) 0.018(3) 0.032(3) C2B 0.061(3) 0.064(3) 0.056(3) 0.010(3) 0.017(2) 0.026(2) C3B 0.059(3) 0.058(3) 0.061(3) 0.004(3) 0.018(2) 0.031(2) C4B 0.061(3) 0.070(3) 0.050(3) 0.011(2) 0.020(2) 0.026(3) C5B 0.074(3) 0.065(3) 0.065(3) 0.011(3) 0.025(2) 0.034(3) C6B 0.078(3) 0.068(4) 0.075(3) 0.018(3) 0.027(3) 0.020(3) C7B 0.098(4) 0.066(4) 0.097(4) 0.012(3) 0.026(3) 0.035(4) C8B 0.081(4) 0.071(4) 0.130(4) 0.007(3) 0.035(3) 0.041(3) C9B 0.069(3) 0.066(4) 0.106(4) 0.014(3) 0.036(3) 0.025(3) C10B 0.086(4) 0.067(3) 0.059(3) 0.016(3) 0.032(3) 0.046(3) C11B 0.093(4) 0.097(4) 0.068(3) 0.018(3) 0.031(3) 0.049(3) C12B 0.110(4) 0.117(5) 0.063(4) 0.007(4) 0.018(4) 0.059(4) C13B 0.105(5) 0.103(5) 0.080(4) -0.010(4) -0.001(4) 0.057(4) C14B 0.073(4) 0.067(4) 0.110(4) 0.002(4) 0.009(4) 0.025(3) C15B 0.083(3) 0.070(3) 0.077(3) 0.020(3) 0.027(3) 0.038(3) O2B 0.082(2) 0.099(2) 0.073(2) -0.0024(19) -0.0043(17) 0.0486(19) N1B 0.080(2) 0.080(3) 0.062(2) -0.005(2) -0.002(2) 0.048(2) C16B 0.072(3) 0.063(3) 0.068(3) 0.006(3) 0.016(3) 0.027(3) C17B 0.066(3) 0.091(4) 0.071(3) 0.009(3) 0.018(3) 0.044(3) C18B 0.066(3) 0.093(4) 0.067(3) 0.002(3) 0.025(3) 0.011(3) C19B 0.083(4) 0.067(3) 0.072(4) 0.013(3) 0.003(3) 0.025(3) C20B 0.083(3) 0.081(4) 0.056(3) 0.001(3) 0.013(3) 0.047(3) C21B 0.121(4) 0.101(4) 0.098(3) -0.012(3) -0.008(3) 0.078(3) O1W 0.144(3) 0.143(4) 0.100(3) -0.018(3) 0.032(3) 0.053(3) _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 O1A C3A 1.434(5) . ? O1A H1OA 0.75(4) . ? C1A C2A 1.176(5) . ? C1A C1B 1.393(6) . ? C2A C3A 1.461(5) . ? C3A C10A 1.511(5) . ? C3A C4A 1.518(5) . ? C4A C5A 1.367(5) . ? C4A C9A 1.373(5) . ? C5A C6A 1.400(6) . ? C5A H5A 0.9300 . ? C6A C7A 1.352(6) . ? C6A H6A 0.9300 . ? C7A C8A 1.362(6) . ? C7A H7A 0.9300 . ? C8A C9A 1.382(5) . ? C8A H8A 0.9300 . ? C9A H9A 0.9300 . ? C10A C15A 1.366(5) . ? C10A C11A 1.378(5) . ? C11A C12A 1.393(6) . ? C11A H11A 0.9300 . ? C12A C13A 1.363(6) . ? C12A H12A 0.9300 . ? C13A C14A 1.350(6) . ? C13A H13A 0.9300 . ? C14A C15A 1.399(5) . ? C14A H14A 0.9300 . ? C15A H15A 0.9300 . ? C16A O2A 1.241(4) . ? C16A N1A 1.339(4) . ? C16A C17A 1.521(5) . ? C17A C18A 1.502(5) . ? C17A C20B 1.611(5) . ? C17A H17A 0.9800 . ? C18A C19A 1.296(5) . ? C18A H18A 0.9300 . ? C19A C20A 1.497(5) . ? C19A H19A 0.9300 . ? C20A N1A 1.472(4) . ? C20A C21A 1.539(4) . ? C20A C17B 1.615(5) . ? C21A H21A 0.9600 . ? C21A H21B 0.9600 . ? C21A H21C 0.9600 . ? N1A H1NA 0.8600 . ? O1B C3B 1.432(4) . ? O1B H1OB 0.85(3) . ? C1B C2B 1.183(5) . ? C2B C3B 1.486(5) . ? C3B C4B 1.520(5) . ? C3B C10B 1.546(5) . ? C4B C5B 1.372(5) . ? C4B C9B 1.392(5) . ? C5B C6B 1.388(5) . ? C5B H5B 0.9300 . ? C6B C7B 1.361(5) . ? C6B H6B 0.9300 . ? C7B C8B 1.367(5) . ? C7B H7B 0.9300 . ? C8B C9B 1.384(5) . ? C8B H8B 0.9300 . ? C9B H9B 0.9300 . ? C10B C11B 1.376(5) . ? C10B C15B 1.385(5) . ? C11B C12B 1.401(5) . ? C11B H11B 0.9300 . ? C12B C13B 1.367(6) . ? C12B H12B 0.9300 . ? C13B C14B 1.357(6) . ? C13B H13B 0.9300 . ? C14B C15B 1.408(5) . ? C14B H14B 0.9300 . ? C15B H15B 0.9300 . ? O2B C16B 1.235(4) . ? N1B C16B 1.327(4) . ? N1B C20B 1.458(4) . ? N1B H1NB 0.8600 . ? C16B C17B 1.519(5) . ? C17B C18B 1.488(5) . ? C17B H17B 0.9800 . ? C18B C19B 1.316(5) . ? C18B H18B 0.9300 . ? C19B C20B 1.486(5) . ? C19B H19B 0.9300 . ? C20B C21B 1.532(4) . ? C21B H21D 0.9600 . ? C21B H21E 0.9600 . ? C21B H21F 0.9600 . ? O1W H1WA 0.95(4) . ? O1W H1WB 1.13(8) . ? 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 C3A O1A H1OA 105(4) . . ? C2A C1A C1B 178.1(5) . . ? C1A C2A C3A 175.1(4) . . ? O1A C3A C2A 108.2(3) . . ? O1A C3A C10A 110.6(3) . . ? C2A C3A C10A 112.0(4) . . ? O1A C3A C4A 106.9(4) . . ? C2A C3A C4A 109.5(4) . . ? C10A C3A C4A 109.6(3) . . ? C5A C4A C9A 118.7(4) . . ? C5A C4A C3A 120.3(5) . . ? C9A C4A C3A 121.0(5) . . ? C4A C5A C6A 119.6(5) . . ? C4A C5A H5A 120.2 . . ? C6A C5A H5A 120.2 . . ? C7A C6A C5A 120.7(5) . . ? C7A C6A H6A 119.7 . . ? C5A C6A H6A 119.7 . . ? C6A C7A C8A 120.2(6) . . ? C6A C7A H7A 119.9 . . ? C8A C7A H7A 119.9 . . ? C7A C8A C9A 119.2(5) . . ? C7A C8A H8A 120.4 . . ? C9A C8A H8A 120.4 . . ? C4A C9A C8A 121.5(5) . . ? C4A C9A H9A 119.2 . . ? C8A C9A H9A 119.2 . . ? C15A C10A C11A 119.2(5) . . ? C15A C10A C3A 122.1(5) . . ? C11A C10A C3A 118.7(5) . . ? C10A C11A C12A 119.5(5) . . ? C10A C11A H11A 120.3 . . ? C12A C11A H11A 120.3 . . ? C13A C12A C11A 120.2(6) . . ? C13A C12A H12A 119.9 . . ? C11A C12A H12A 119.9 . . ? C14A C13A C12A 121.1(6) . . ? C14A C13A H13A 119.4 . . ? C12A C13A H13A 119.4 . . ? C13A C14A C15A 118.8(6) . . ? C13A C14A H14A 120.6 . . ? C15A C14A H14A 120.6 . . ? C10A C15A C14A 121.2(5) . . ? C10A C15A H15A 119.4 . . ? C14A C15A H15A 119.4 . . ? O2A C16A N1A 122.5(4) . . ? O2A C16A C17A 123.6(4) . . ? N1A C16A C17A 113.9(4) . . ? C18A C17A C16A 108.9(4) . . ? C18A C17A C20B 111.7(3) . . ? C16A C17A C20B 111.5(3) . . ? C18A C17A H17A 108.2 . . ? C16A C17A H17A 108.2 . . ? C20B C17A H17A 108.2 . . ? C19A C18A C17A 117.9(5) . . ? C19A C18A H18A 121.0 . . ? C17A C18A H18A 121.0 . . ? C18A C19A C20A 118.6(4) . . ? C18A C19A H19A 120.7 . . ? C20A C19A H19A 120.7 . . ? N1A C20A C19A 107.1(3) . . ? N1A C20A C21A 107.8(3) . . ? C19A C20A C21A 113.5(4) . . ? N1A C20A C17B 110.8(3) . . ? C19A C20A C17B 109.7(4) . . ? C21A C20A C17B 107.9(4) . . ? C20A C21A H21A 109.5 . . ? C20A C21A H21B 109.5 . . ? H21A C21A H21B 109.5 . . ? C20A C21A H21C 109.5 . . ? H21A C21A H21C 109.5 . . ? H21B C21A H21C 109.5 . . ? C16A N1A C20A 121.0(3) . . ? C16A N1A H1NA 119.5 . . ? C20A N1A H1NA 119.5 . . ? C3B O1B H1OB 108(3) . . ? C2B C1B C1A 178.1(5) . . ? C1B C2B C3B 178.2(5) . . ? O1B C3B C2B 110.8(3) . . ? O1B C3B C4B 106.4(4) . . ? C2B C3B C4B 109.3(3) . . ? O1B C3B C10B 108.6(3) . . ? C2B C3B C10B 112.4(4) . . ? C4B C3B C10B 109.1(3) . . ? C5B C4B C9B 117.6(4) . . ? C5B C4B C3B 122.7(4) . . ? C9B C4B C3B 119.7(4) . . ? C4B C5B C6B 120.5(4) . . ? C4B C5B H5B 119.7 . . ? C6B C5B H5B 119.7 . . ? C7B C6B C5B 121.4(4) . . ? C7B C6B H6B 119.3 . . ? C5B C6B H6B 119.3 . . ? C6B C7B C8B 119.0(5) . . ? C6B C7B H7B 120.5 . . ? C8B C7B H7B 120.5 . . ? C7B C8B C9B 120.2(4) . . ? C7B C8B H8B 119.9 . . ? C9B C8B H8B 119.9 . . ? C8B C9B C4B 121.3(4) . . ? C8B C9B H9B 119.3 . . ? C4B C9B H9B 119.3 . . ? C11B C10B C15B 118.8(4) . . ? C11B C10B C3B 119.8(5) . . ? C15B C10B C3B 121.3(4) . . ? C10B C11B C12B 121.1(5) . . ? C10B C11B H11B 119.5 . . ? C12B C11B H11B 119.5 . . ? C13B C12B C11B 118.9(5) . . ? C13B C12B H12B 120.5 . . ? C11B C12B H12B 120.5 . . ? C14B C13B C12B 121.5(6) . . ? C14B C13B H13B 119.3 . . ? C12B C13B H13B 119.3 . . ? C13B C14B C15B 119.6(5) . . ? C13B C14B H14B 120.2 . . ? C15B C14B H14B 120.2 . . ? C10B C15B C14B 120.1(4) . . ? C10B C15B H15B 120.0 . . ? C14B C15B H15B 120.0 . . ? C16B N1B C20B 121.1(3) . . ? C16B N1B H1NB 119.4 . . ? C20B N1B H1NB 119.4 . . ? O2B C16B N1B 123.9(4) . . ? O2B C16B C17B 121.1(4) . . ? N1B C16B C17B 115.0(4) . . ? C18B C17B C16B 108.3(4) . . ? C18B C17B C20A 111.4(3) . . ? C16B C17B C20A 110.6(4) . . ? C18B C17B H17B 108.8 . . ? C16B C17B H17B 108.8 . . ? C20A C17B H17B 108.8 . . ? C19B C18B C17B 118.4(4) . . ? C19B C18B H18B 120.8 . . ? C17B C18B H18B 120.8 . . ? C18B C19B C20B 118.3(4) . . ? C18B C19B H19B 120.8 . . ? C20B C19B H19B 120.8 . . ? N1B C20B C19B 106.7(3) . . ? N1B C20B C21B 107.1(3) . . ? C19B C20B C21B 112.3(4) . . ? N1B C20B C17A 111.3(4) . . ? C19B C20B C17A 109.3(3) . . ? C21B C20B C17A 110.1(4) . . ? C20B C21B H21D 109.5 . . ? C20B C21B H21E 109.5 . . ? H21D C21B H21E 109.5 . . ? C20B C21B H21F 109.5 . . ? H21D C21B H21F 109.5 . . ? H21E C21B H21F 109.5 . . ? H1WA O1W H1WB 90(4) . . ? 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 C1B C1A C2A C3A -38(19) . . . . ? C1A C2A C3A O1A -3(6) . . . . ? C1A C2A C3A C10A -125(6) . . . . ? C1A C2A C3A C4A 113(6) . . . . ? O1A C3A C4A C5A -15.7(5) . . . . ? C2A C3A C4A C5A -132.7(4) . . . . ? C10A C3A C4A C5A 104.1(5) . . . . ? O1A C3A C4A C9A 165.9(4) . . . . ? C2A C3A C4A C9A 48.9(5) . . . . ? C10A C3A C4A C9A -74.3(5) . . . . ? C9A C4A C5A C6A 0.3(7) . . . . ? C3A C4A C5A C6A -178.1(4) . . . . ? C4A C5A C6A C7A -1.9(8) . . . . ? C5A C6A C7A C8A 2.1(9) . . . . ? C6A C7A C8A C9A -0.7(8) . . . . ? C5A C4A C9A C8A 1.1(6) . . . . ? C3A C4A C9A C8A 179.5(4) . . . . ? C7A C8A C9A C4A -1.0(7) . . . . ? O1A C3A C10A C15A -131.8(4) . . . . ? C2A C3A C10A C15A -11.1(6) . . . . ? C4A C3A C10A C15A 110.6(5) . . . . ? O1A C3A C10A C11A 49.8(5) . . . . ? C2A C3A C10A C11A 170.4(4) . . . . ? C4A C3A C10A C11A -67.8(5) . . . . ? C15A C10A C11A C12A -0.3(6) . . . . ? C3A C10A C11A C12A 178.2(4) . . . . ? C10A C11A C12A C13A -0.6(7) . . . . ? C11A C12A C13A C14A 1.3(9) . . . . ? C12A C13A C14A C15A -1.1(8) . . . . ? C11A C10A C15A C14A 0.5(7) . . . . ? C3A C10A C15A C14A -177.9(4) . . . . ? C13A C14A C15A C10A 0.2(7) . . . . ? O2A C16A C17A C18A 136.1(4) . . . . ? N1A C16A C17A C18A -41.4(5) . . . . ? O2A C16A C17A C20B -100.2(4) . . . . ? N1A C16A C17A C20B 82.3(4) . . . . ? C16A C17A C18A C19A 44.7(5) . . . . ? C20B C17A C18A C19A -79.0(5) . . . . ? C17A C18A C19A C20A -1.5(7) . . . . ? C18A C19A C20A N1A -42.3(6) . . . . ? C18A C19A C20A C21A -161.1(4) . . . . ? C18A C19A C20A C17B 78.0(5) . . . . ? O2A C16A N1A C20A 179.4(4) . . . . ? C17A C16A N1A C20A -3.1(5) . . . . ? C19A C20A N1A C16A 44.9(5) . . . . ? C21A C20A N1A C16A 167.4(4) . . . . ? C17B C20A N1A C16A -74.7(5) . . . . ? C2A C1A C1B C2B -5(25) . . . . ? C1A C1B C2B C3B 143(12) . . . . ? C1B C2B C3B O1B 95(14) . . . . ? C1B C2B C3B C4B -22(14) . . . . ? C1B C2B C3B C10B -144(14) . . . . ? O1B C3B C4B C5B -5.2(5) . . . . ? C2B C3B C4B C5B 114.5(4) . . . . ? C10B C3B C4B C5B -122.2(4) . . . . ? O1B C3B C4B C9B 176.6(3) . . . . ? C2B C3B C4B C9B -63.7(5) . . . . ? C10B C3B C4B C9B 59.6(5) . . . . ? C9B C4B C5B C6B -0.3(6) . . . . ? C3B C4B C5B C6B -178.6(3) . . . . ? C4B C5B C6B C7B 1.2(6) . . . . ? C5B C6B C7B C8B -1.1(7) . . . . ? C6B C7B C8B C9B 0.1(7) . . . . ? C7B C8B C9B C4B 0.7(7) . . . . ? C5B C4B C9B C8B -0.6(6) . . . . ? C3B C4B C9B C8B 177.7(4) . . . . ? O1B C3B C10B C11B -51.8(5) . . . . ? C2B C3B C10B C11B -174.8(3) . . . . ? C4B C3B C10B C11B 63.8(5) . . . . ? O1B C3B C10B C15B 129.3(4) . . . . ? C2B C3B C10B C15B 6.3(5) . . . . ? C4B C3B C10B C15B -115.1(4) . . . . ? C15B C10B C11B C12B 0.6(6) . . . . ? C3B C10B C11B C12B -178.4(4) . . . . ? C10B C11B C12B C13B -0.1(7) . . . . ? C11B C12B C13B C14B -0.3(8) . . . . ? C12B C13B C14B C15B 0.2(8) . . . . ? C11B C10B C15B C14B -0.7(6) . . . . ? C3B C10B C15B C14B 178.2(3) . . . . ? C13B C14B C15B C10B 0.3(7) . . . . ? C20B N1B C16B O2B -176.7(4) . . . . ? C20B N1B C16B C17B 5.2(6) . . . . ? O2B C16B C17B C18B -138.7(4) . . . . ? N1B C16B C17B C18B 39.5(5) . . . . ? O2B C16B C17B C20A 99.0(4) . . . . ? N1B C16B C17B C20A -82.8(4) . . . . ? N1A C20A C17B C18B -0.8(5) . . . . ? C19A C20A C17B C18B -118.8(4) . . . . ? C21A C20A C17B C18B 117.0(4) . . . . ? N1A C20A C17B C16B 119.7(4) . . . . ? C19A C20A C17B C16B 1.7(5) . . . . ? C21A C20A C17B C16B -122.5(4) . . . . ? C16B C17B C18B C19B -43.2(5) . . . . ? C20A C17B C18B C19B 78.6(5) . . . . ? C17B C18B C19B C20B 1.2(6) . . . . ? C16B N1B C20B C19B -46.4(5) . . . . ? C16B N1B C20B C21B -166.9(4) . . . . ? C16B N1B C20B C17A 72.7(5) . . . . ? C18B C19B C20B N1B 42.6(5) . . . . ? C18B C19B C20B C21B 159.7(4) . . . . ? C18B C19B C20B C17A -77.8(5) . . . . ? C18A C17A C20B N1B 1.9(5) . . . . ? C16A C17A C20B N1B -120.2(4) . . . . ? C18A C17A C20B C19B 119.5(4) . . . . ? C16A C17A C20B C19B -2.6(5) . . . . ? C18A C17A C20B C21B -116.7(4) . . . . ? C16A C17A C20B C21B 121.1(4) . . . . ? _diffrn_measured_fraction_theta_max 0.875 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 0.875 _refine_diff_density_max 0.117 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.035 # Attachment '1-a.cif' data_hp1r0 _database_code_depnum_ccdc_archive 'CCDC 603857' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,1,6,6-tetraphenyl-2,4- hexadiyne-1,6-diol bis(6-methyl-2-(1H)-pyridone) clathrate ; _chemical_name_common ; 1,1,6,6-tetraphenyl-2,4- hexadiyne-1,6-diol bis(6-methyl-2- (1H)-pyridone) clathrate ; _chemical_melting_point ? _chemical_formula_moiety '(C30 H22 O2), 2(C6 H7 N O)' _chemical_formula_sum 'C21 H18 N O2' _chemical_formula_weight 316.36 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 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.4564(4) _cell_length_b 10.8394(4) _cell_length_c 11.3593(6) _cell_angle_alpha 64.012(3) _cell_angle_beta 79.957(2) _cell_angle_gamma 68.499(2) _cell_volume 870.69(7) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3149 _cell_measurement_theta_min 1.018 _cell_measurement_theta_max 27.485 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.207 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 334 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9697 _exptl_absorpt_correction_T_max 0.9923 _exptl_absorpt_process_details none _exptl_special_details ; ? ; _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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 5354 _diffrn_reflns_av_R_equivalents 0.0278 _diffrn_reflns_av_sigmaI/netI 0.0570 _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 -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 25.04 _reflns_number_total 3053 _reflns_number_gt 1976 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_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^)+(0.0977P)^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 0.16(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3053 _refine_ls_number_parameters 242 _refine_ls_number_restraints 19 _refine_ls_R_factor_all 0.0756 _refine_ls_R_factor_gt 0.0516 _refine_ls_wR_factor_ref 0.1663 _refine_ls_wR_factor_gt 0.1578 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.065 _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 0.15643(17) 0.27600(14) 0.16484(12) 0.0713(5) Uani 1 1 d . . . H1 H 0.2334 0.2012 0.1693 0.107 Uiso 1 1 calc R . . C1 C 0.0278(2) 0.0569(2) 0.45771(18) 0.0578(5) Uani 1 1 d . . . C2 C 0.0787(2) 0.15482(19) 0.38442(18) 0.0553(5) Uani 1 1 d . . . C3 C 0.1281(2) 0.28125(18) 0.29068(16) 0.0542(5) Uani 1 1 d . . . C4 C 0.2867(2) 0.2859(2) 0.3337(2) 0.0617(5) Uani 1 1 d . . . C5 C 0.3468(3) 0.3991(3) 0.2548(3) 0.0925(8) Uani 1 1 d . . . H5 H 0.2915 0.4693 0.1775 0.111 Uiso 1 1 calc R . . C6 C 0.4887(4) 0.4087(4) 0.2899(4) 0.1254(13) Uani 1 1 d . . . H6 H 0.5283 0.4854 0.2364 0.150 Uiso 1 1 calc R . . C7 C 0.5711(3) 0.3060(4) 0.4029(5) 0.1271(14) Uani 1 1 d . . . H7 H 0.6670 0.3128 0.4258 0.152 Uiso 1 1 calc R . . C8 C 0.5137(3) 0.1943(3) 0.4818(3) 0.0988(9) Uani 1 1 d . . . H8 H 0.5700 0.1244 0.5588 0.119 Uiso 1 1 calc R . . C9 C 0.3707(2) 0.1844(2) 0.4476(2) 0.0723(6) Uani 1 1 d . . . H9 H 0.3311 0.1079 0.5024 0.087 Uiso 1 1 calc R . . C10 C -0.0207(2) 0.41887(18) 0.28067(17) 0.0540(5) Uani 1 1 d . . . C11 C -0.1005(3) 0.5193(2) 0.1649(2) 0.0729(6) Uani 1 1 d . . . H11 H -0.0675 0.5031 0.0890 0.087 Uiso 1 1 calc R . . C12 C -0.2306(3) 0.6451(2) 0.1607(2) 0.0806(7) Uani 1 1 d . . . H12 H -0.2826 0.7133 0.0816 0.097 Uiso 1 1 calc R . . C13 C -0.2822(3) 0.6693(2) 0.2710(3) 0.0790(7) Uani 1 1 d . . . H13 H -0.3688 0.7541 0.2672 0.095 Uiso 1 1 calc R . . C14 C -0.2063(3) 0.5681(2) 0.3889(2) 0.0790(6) Uani 1 1 d . . . H14 H -0.2430 0.5833 0.4651 0.095 Uiso 1 1 calc R . . C15 C -0.0754(2) 0.4440(2) 0.3930(2) 0.0670(6) Uani 1 1 d . . . H15 H -0.0232 0.3763 0.4722 0.080 Uiso 1 1 calc R . . O2 O 0.4605(2) 0.05178(18) 0.13441(16) 0.0725(6) Uani 0.832(3) 1 d PD . . N1 N 0.65732(19) 0.09093(17) -0.02858(15) 0.0705(5) Uani 1 1 d D . . H1N1 H 0.613(3) 0.049(3) -0.082(2) 0.094(8) Uiso 0.832(3) 1 d PD . . C16 C 0.5887(2) 0.0950(2) 0.08755(17) 0.0656(7) Uani 0.832(3) 1 d PD . . C17 C 0.7843(3) 0.1459(3) -0.0954(2) 0.0807(8) Uani 0.832(3) 1 d PD . . C18 C 0.8617(3) 0.1950(3) -0.0393(3) 0.0954(8) Uani 1 1 d D . . H18 H 0.959(4) 0.234(3) -0.082(3) 0.105(9) Uiso 0.832(3) 1 d P . . C19 C 0.8006(4) 0.1940(3) 0.0857(3) 0.1023(11) Uani 0.832(3) 1 d PD . . H19 H 0.8515 0.2293 0.1249 0.123 Uiso 0.832(3) 1 calc PR . . C20 C 0.6727(3) 0.1444(3) 0.1495(2) 0.0960(8) Uani 1 1 d D . . H20 H 0.6387 0.1419 0.2326 0.115 Uiso 0.832(3) 1 calc PR . . C21 C 0.8299(5) 0.1493(5) -0.2292(3) 0.1168(17) Uiso 0.832(3) 1 d PD . . H21A H 0.7491 0.1235 -0.2557 0.175 Uiso 0.832(3) 1 calc PRD . . H21B H 0.9415 0.0813 -0.2286 0.175 Uiso 0.832(3) 1 calc PRD . . H21C H 0.8286 0.2453 -0.2896 0.175 Uiso 0.832(3) 1 calc PRD . . O2D O 0.6213(11) -0.0174(10) -0.1418(9) 0.077(3) Uiso 0.168(3) 1 d PD . . C16D C 0.7122(13) 0.0473(13) -0.1284(8) 0.078(4) Uiso 0.168(3) 1 d PD . . C17D C 0.7493(16) 0.1271(17) 0.0319(5) 0.107(5) Uiso 0.168(3) 1 d PD . . C19D C 0.887(2) 0.1712(19) -0.1557(10) 0.120(6) Uiso 0.168(3) 1 d PD . . H19D H 0.9576 0.2209 -0.2133 0.144 Uiso 0.168(3) 1 calc PR . . C20D C 0.8435(14) 0.1010(14) -0.2101(10) 0.054(3) Uiso 0.168(3) 1 d PD . . H20D H 0.8894 0.0891 -0.2865 0.065 Uiso 0.168(3) 1 calc PR . . 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 0.0734(10) 0.0669(9) 0.0638(8) -0.0282(7) 0.0059(7) -0.0136(7) C1 0.0520(11) 0.0506(10) 0.0700(11) -0.0256(9) 0.0002(9) -0.0155(8) C2 0.0490(11) 0.0489(10) 0.0673(11) -0.0260(9) -0.0016(8) -0.0122(9) C3 0.0518(10) 0.0491(10) 0.0581(10) -0.0207(8) 0.0054(8) -0.0169(8) C4 0.0464(10) 0.0503(10) 0.0897(13) -0.0342(10) 0.0057(10) -0.0133(9) C5 0.0683(15) 0.0678(13) 0.137(2) -0.0375(14) 0.0162(14) -0.0316(12) C6 0.074(2) 0.104(2) 0.229(4) -0.092(3) 0.035(2) -0.0509(19) C7 0.0500(16) 0.132(3) 0.256(4) -0.138(3) 0.006(2) -0.0218(18) C8 0.0592(14) 0.0996(18) 0.165(2) -0.0921(19) -0.0266(15) 0.0031(13) C9 0.0528(12) 0.0653(12) 0.1061(16) -0.0492(12) -0.0096(11) -0.0061(10) C10 0.0474(10) 0.0477(10) 0.0623(11) -0.0187(9) 0.0026(8) -0.0168(8) C11 0.0632(13) 0.0698(13) 0.0650(12) -0.0179(10) 0.0023(10) -0.0129(11) C12 0.0630(14) 0.0638(13) 0.0791(14) -0.0101(11) -0.0030(11) -0.0049(11) C13 0.0589(13) 0.0569(12) 0.1094(18) -0.0341(13) -0.0032(12) -0.0053(10) C14 0.0670(14) 0.0755(14) 0.0983(16) -0.0501(13) -0.0056(12) -0.0077(12) C15 0.0599(12) 0.0635(12) 0.0741(12) -0.0327(10) -0.0078(9) -0.0077(10) O2 0.0634(12) 0.0729(11) 0.0855(12) -0.0413(9) 0.0047(9) -0.0186(9) N1 0.0585(10) 0.0686(11) 0.0889(12) -0.0386(9) 0.0029(9) -0.0195(9) C16 0.0519(14) 0.0553(13) 0.0853(17) -0.0323(12) -0.0042(12) -0.0073(11) C17 0.0624(17) 0.0731(17) 0.0948(19) -0.0270(15) 0.0081(14) -0.0228(14) C18 0.0753(17) 0.0839(17) 0.131(2) -0.0426(16) 0.0017(15) -0.0341(14) C19 0.082(2) 0.100(2) 0.150(3) -0.067(2) -0.016(2) -0.0312(18) C20 0.0866(18) 0.1051(19) 0.1182(19) -0.0686(17) -0.0016(15) -0.0264(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 C3 1.430(2) . ? O1 H1 0.8200 . ? C1 C2 1.200(2) . ? C1 C1 1.377(4) 2_556 ? C2 C3 1.474(2) . ? C3 C4 1.530(3) . ? C3 C10 1.532(2) . ? C4 C9 1.374(3) . ? C4 C5 1.379(3) . ? C5 C6 1.380(4) . ? C5 H5 0.9300 . ? C6 C7 1.365(5) . ? C6 H6 0.9300 . ? C7 C8 1.354(5) . ? C7 H7 0.9300 . ? C8 C9 1.386(3) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.373(3) . ? C10 C15 1.386(3) . ? C11 C12 1.391(3) . ? C11 H11 0.9300 . ? C12 C13 1.357(3) . ? C12 H12 0.9300 . ? C13 C14 1.380(3) . ? C13 H13 0.9300 . ? C14 C15 1.382(3) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? O2 O2D 0.875(7) 2_655 ? O2 C16 1.2769(10) . ? N1 C16 1.3578(10) . ? N1 C16D 1.3594(10) . ? N1 C17 1.3685(10) . ? N1 C17D 1.3701(10) . ? N1 H1N1 1.0799(10) . ? C16 C20 1.4384(10) . ? C16 C17D 1.490(6) . ? C17 C18 1.3480(10) . ? C17 C17D 1.363(5) . ? C17 C21 1.4889(10) . ? C17 C16D 1.600(7) . ? C18 C17D 1.3498(10) . ? C18 C19 1.4207(10) . ? C18 C19D 1.4212(10) . ? C18 H18 1.01(3) . ? C19 C20 1.3404(10) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? O2D O2 0.875(7) 2_655 ? O2D C16D 1.2797(10) . ? O2D H1N1 1.165(13) . ? C16D C20D 1.4400(10) . ? C16D H1N1 0.91(3) . ? C19D C20D 1.3406(10) . ? C19D H18 1.58(3) . ? C19D H19D 0.9300 . ? C20D H20D 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 O1 H1 109.5 . . ? C2 C1 C1 179.1(3) . 2_556 ? C1 C2 C3 175.73(19) . . ? O1 C3 C2 108.67(14) . . ? O1 C3 C4 110.40(14) . . ? C2 C3 C4 112.08(15) . . ? O1 C3 C10 108.32(14) . . ? C2 C3 C10 107.97(14) . . ? C4 C3 C10 109.30(13) . . ? C9 C4 C5 118.5(2) . . ? C9 C4 C3 123.39(17) . . ? C5 C4 C3 118.1(2) . . ? C4 C5 C6 120.3(3) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C7 C6 C5 120.3(3) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C8 C7 C6 120.2(3) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C7 C8 C9 119.8(3) . . ? C7 C8 H8 120.1 . . ? C9 C8 H8 120.1 . . ? C4 C9 C8 120.9(2) . . ? C4 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C11 C10 C15 118.67(17) . . ? C11 C10 C3 122.80(16) . . ? C15 C10 C3 118.52(16) . . ? C10 C11 C12 120.26(19) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C13 C12 C11 120.6(2) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C12 C13 C14 120.01(19) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C13 C14 C15 119.5(2) . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? C14 C15 C10 120.95(19) . . ? C14 C15 H15 119.5 . . ? C10 C15 H15 119.5 . . ? O2D O2 C16 160.3(7) 2_655 . ? C16 N1 C16D 161.5(4) . . ? C16 N1 C17 124.57(16) . . ? C16D N1 C17 71.8(3) . . ? C16 N1 C17D 66.2(3) . . ? C16D N1 C17D 126.4(6) . . ? C17 N1 C17D 59.7(2) . . ? C16 N1 H1N1 123.5(14) . . ? C16D N1 H1N1 41.9(14) . . ? C17 N1 H1N1 111.8(14) . . ? C17D N1 H1N1 167.1(16) . . ? O2 C16 N1 118.58(14) . . ? O2 C16 C20 125.53(17) . . ? N1 C16 C20 115.86(16) . . ? O2 C16 C17D 172.7(6) . . ? N1 C16 C17D 57.28(15) . . ? C20 C16 C17D 58.8(2) . . ? C18 C17 C17D 59.72(12) . . ? C18 C17 N1 119.6(2) . . ? C17D C17 N1 60.22(11) . . ? C18 C17 C21 122.8(2) . . ? C17D C17 C21 173.9(7) . . ? N1 C17 C21 117.6(2) . . ? C18 C17 C16D 164.4(5) . . ? C17D C17 C16D 110.4(3) . . ? N1 C17 C16D 53.82(18) . . ? C21 C17 C16D 65.8(3) . . ? C17 C18 C17D 60.7(2) . . ? C17 C18 C19 117.7(2) . . ? C17D C18 C19 57.9(3) . . ? C17 C18 C19D 44.5(6) . . ? C17D C18 C19D 104.1(7) . . ? C19 C18 C19D 161.9(7) . . ? C17 C18 H18 123.6(17) . . ? C17D C18 H18 171.1(18) . . ? C19 C18 H18 118.7(16) . . ? C19D C18 H18 79.2(17) . . ? C20 C19 C18 122.7(2) . . ? C20 C19 H19 118.7 . . ? C18 C19 H19 118.7 . . ? C19 C20 C16 119.1(2) . . ? C19 C20 H20 120.4 . . ? C16 C20 H20 120.4 . . ? C17 C21 H21A 109.5 . . ? C17 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C17 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O2 O2D C16D 162.8(11) 2_655 . ? O2 O2D H1N1 119.4(15) 2_655 . ? C16D O2D H1N1 43.4(13) . . ? O2D C16D N1 113.1(6) . . ? O2D C16D C20D 131.7(6) . . ? N1 C16D C20D 114.4(6) . . ? O2D C16D C17 166.0(7) . . ? N1 C16D C17 54.34(18) . . ? C20D C16D C17 60.1(5) . . ? O2D C16D H1N1 61.5(7) . . ? N1 C16D H1N1 52.39(15) . . ? C20D C16D H1N1 159(2) . . ? C17 C16D H1N1 104.9(6) . . ? C18 C17D C17 59.60(13) . . ? C18 C17D N1 119.3(2) . . ? C17 C17D N1 60.10(13) . . ? C18 C17D C16 162.9(13) . . ? C17 C17D C16 115.5(2) . . ? N1 C17D C16 56.49(15) . . ? C20D C19D C18 141.1(12) . . ? C20D C19D H18 172(2) . . ? C18 C19D H18 39.0(11) . . ? C20D C19D H19D 109.4 . . ? C18 C19D H19D 109.4 . . ? H18 C19D H19D 71.4 . . ? C19D C20D C16D 107.3(10) . . ? C19D C20D H20D 126.4 . . ? C16D C20D H20D 126.4 . . ? 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 C1 C1 C2 C3 166(14) 2_556 . . . ? C1 C2 C3 O1 -82(2) . . . . ? C1 C2 C3 C4 156(2) . . . . ? C1 C2 C3 C10 35(2) . . . . ? O1 C3 C4 C9 -122.03(19) . . . . ? C2 C3 C4 C9 -0.7(2) . . . . ? C10 C3 C4 C9 118.92(18) . . . . ? O1 C3 C4 C5 58.8(2) . . . . ? C2 C3 C4 C5 -179.91(17) . . . . ? C10 C3 C4 C5 -60.3(2) . . . . ? C9 C4 C5 C6 0.3(3) . . . . ? C3 C4 C5 C6 179.5(2) . . . . ? C4 C5 C6 C7 0.2(4) . . . . ? C5 C6 C7 C8 -0.4(5) . . . . ? C6 C7 C8 C9 0.0(4) . . . . ? C5 C4 C9 C8 -0.7(3) . . . . ? C3 C4 C9 C8 -179.84(17) . . . . ? C7 C8 C9 C4 0.5(3) . . . . ? O1 C3 C10 C11 -3.4(2) . . . . ? C2 C3 C10 C11 -120.88(19) . . . . ? C4 C3 C10 C11 117.0(2) . . . . ? O1 C3 C10 C15 177.57(15) . . . . ? C2 C3 C10 C15 60.1(2) . . . . ? C4 C3 C10 C15 -62.1(2) . . . . ? C15 C10 C11 C12 1.6(3) . . . . ? C3 C10 C11 C12 -177.42(17) . . . . ? C10 C11 C12 C13 -1.1(3) . . . . ? C11 C12 C13 C14 -0.4(3) . . . . ? C12 C13 C14 C15 1.4(3) . . . . ? C13 C14 C15 C10 -0.8(3) . . . . ? C11 C10 C15 C14 -0.7(3) . . . . ? C3 C10 C15 C14 178.42(18) . . . . ? O2D O2 C16 N1 0(2) 2_655 . . . ? O2D O2 C16 C20 -178(2) 2_655 . . . ? O2D O2 C16 C17D -54(3) 2_655 . . . ? C16D N1 C16 O2 -36.3(17) . . . . ? C17 N1 C16 O2 173.8(2) . . . . ? C17D N1 C16 O2 -173.0(8) . . . . ? C16D N1 C16 C20 141.8(17) . . . . ? C17 N1 C16 C20 -8.2(3) . . . . ? C17D N1 C16 C20 5.1(8) . . . . ? C16D N1 C16 C17D 136.7(19) . . . . ? C17 N1 C16 C17D -13.2(8) . . . . ? C16 N1 C17 C18 7.2(4) . . . . ? C16D N1 C17 C18 -163.2(7) . . . . ? C17D N1 C17 C18 -6.8(9) . . . . ? C16 N1 C17 C17D 14.0(9) . . . . ? C16D N1 C17 C17D -156.3(10) . . . . ? C16 N1 C17 C21 -172.5(3) . . . . ? C16D N1 C17 C21 17.2(6) . . . . ? C17D N1 C17 C21 173.5(9) . . . . ? C16 N1 C17 C16D 170.4(6) . . . . ? C17D N1 C17 C16D 156.3(10) . . . . ? N1 C17 C18 C17D 6.9(9) . . . . ? C21 C17 C18 C17D -173.5(9) . . . . ? C16D C17 C18 C17D -53.7(14) . . . . ? C17D C17 C18 C19 -10.1(9) . . . . ? N1 C17 C18 C19 -3.2(4) . . . . ? C21 C17 C18 C19 176.4(3) . . . . ? C16D C17 C18 C19 -63.8(12) . . . . ? C17D C17 C18 C19D 166.0(14) . . . . ? N1 C17 C18 C19D 172.9(12) . . . . ? C21 C17 C18 C19D -7.4(11) . . . . ? C16D C17 C18 C19D 112.4(16) . . . . ? C17 C18 C19 C20 1.2(5) . . . . ? C17D C18 C19 C20 -9.2(9) . . . . ? C19D C18 C19 C20 -8(3) . . . . ? C18 C19 C20 C16 -2.4(4) . . . . ? O2 C16 C20 C19 -176.5(2) . . . . ? N1 C16 C20 C19 5.6(4) . . . . ? C17D C16 C20 C19 10.6(8) . . . . ? O2 O2D C16D N1 11(5) 2_655 . . . ? O2 O2D C16D C20D -159(3) 2_655 . . . ? O2 O2D C16D C17 -14(8) 2_655 . . . ? C16 N1 C16D O2D 33(2) . . . . ? C17 N1 C16D O2D -172.9(12) . . . . ? C17D N1 C16D O2D 161.6(10) . . . . ? C16 N1 C16D C20D -156.0(11) . . . . ? C17 N1 C16D C20D -1.7(9) . . . . ? C17D N1 C16D C20D -27.2(15) . . . . ? C16 N1 C16D C17 -154.3(15) . . . . ? C17D N1 C16D C17 -25.5(10) . . . . ? C18 C17 C16D O2D 98(5) . . . . ? C17D C17 C16D O2D 50(5) . . . . ? N1 C17 C16D O2D 28(4) . . . . ? C21 C17 C16D O2D -135(5) . . . . ? C18 C17 C16D N1 69.7(13) . . . . ? C17D C17 C16D N1 21.8(9) . . . . ? C21 C17 C16D N1 -163.3(6) . . . . ? C18 C17 C16D C20D -112.0(12) . . . . ? C17D C17 C16D C20D -159.9(10) . . . . ? N1 C17 C16D C20D 178.2(9) . . . . ? C21 C17 C16D C20D 14.9(7) . . . . ? C19 C18 C17D C17 169.4(9) . . . . ? C19D C18 C17D C17 -10.0(10) . . . . ? C17 C18 C17D N1 -6.9(9) . . . . ? C19 C18 C17D N1 162.6(17) . . . . ? C19D C18 C17D N1 -16.9(17) . . . . ? C17 C18 C17D C16 -77.8(13) . . . . ? C19 C18 C17D C16 92(2) . . . . ? C19D C18 C17D C16 -88(2) . . . . ? N1 C17 C17D C18 -173.1(9) . . . . ? C21 C17 C17D C18 116(3) . . . . ? C16D C17 C17D C18 166.7(6) . . . . ? C18 C17 C17D N1 173.1(9) . . . . ? C21 C17 C17D N1 -71(4) . . . . ? C16D C17 C17D N1 -20.2(8) . . . . ? C18 C17 C17D C16 161.5(15) . . . . ? N1 C17 C17D C16 -11.6(7) . . . . ? C21 C17 C17D C16 -83(4) . . . . ? C16D C17 C17D C16 -31.9(14) . . . . ? C16 N1 C17D C18 -160.6(16) . . . . ? C16D N1 C17D C18 35.1(18) . . . . ? C17 N1 C17D C18 6.8(9) . . . . ? C16 N1 C17D C17 -167.4(8) . . . . ? C16D N1 C17D C17 28.3(11) . . . . ? C16D N1 C17D C16 -164.3(7) . . . . ? C17 N1 C17D C16 167.4(8) . . . . ? O2 C16 C17D C18 138(4) . . . . ? N1 C16 C17D C18 81.1(13) . . . . ? C20 C16 C17D C18 -94(2) . . . . ? O2 C16 C17D C17 69(3) . . . . ? N1 C16 C17D C17 12.1(7) . . . . ? C20 C16 C17D C17 -162.6(15) . . . . ? O2 C16 C17D N1 57(3) . . . . ? C20 C16 C17D N1 -174.7(8) . . . . ? C17 C18 C19D C20D -16.7(19) . . . . ? C17D C18 C19D C20D -4(3) . . . . ? C19 C18 C19D C20D -6(5) . . . . ? C18 C19D C20D C16D 10(3) . . . . ? O2D C16D C20D C19D 174.7(15) . . . . ? N1 C16D C20D C19D 5.6(17) . . . . ? C17 C16D C20D C19D 4.0(11) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.247 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.031 # Attachment '1-b(before water penetration).cif' data_pyr102r12 _database_code_depnum_ccdc_archive 'CCDC 603858' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,1,6,6-tetraphenyl-2,4- hexadiyne-1,6-diol (3,7-Diazatricyclo[4.2.2.22,5]dodeca-9,11-diene-4,8-dione) clathrate ; _chemical_name_common ; 1,1,6,6-tetraphenyl-2,4- hexadiyne-1,6-diol (3,7- Diazatricyclo(4.2.2.22,5)dodeca-9,11-diene-4,8-dione) clathrate ; _chemical_melting_point ? _chemical_formula_moiety '(C30 H22 O2), (C10 H10 N2 O2)' _chemical_formula_sum 'C20 H16 N O2' _chemical_formula_weight 302.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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 7.7433(9) _cell_length_b 7.7868(8) _cell_length_c 13.5188(17) _cell_angle_alpha 88.115(4) _cell_angle_beta 76.675(4) _cell_angle_gamma 86.030(8) _cell_volume 791.16(16) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2565 _cell_measurement_theta_min 1.018 _cell_measurement_theta_max 25.028 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.269 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 318 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9758 _exptl_absorpt_correction_T_max 0.9918 _exptl_absorpt_process_details none _exptl_special_details ; ? ; _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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 4652 _diffrn_reflns_av_R_equivalents 0.0477 _diffrn_reflns_av_sigmaI/netI 0.0718 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2710 _reflns_number_gt 1793 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_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^)+(0.2000P)^2^+0.2000P] 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 0.50(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2710 _refine_ls_number_parameters 216 _refine_ls_number_restraints 20 _refine_ls_R_factor_all 0.1293 _refine_ls_R_factor_gt 0.1001 _refine_ls_wR_factor_ref 0.3199 _refine_ls_wR_factor_gt 0.2983 _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_restrained_S_all 1.100 _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 0.8290(4) 0.1376(3) 0.2376(2) 0.0677(9) Uani 1 1 d . . . H1O1 H 0.893(6) 0.123(6) 0.286(4) 0.089(14) Uiso 1 1 d . . . C1 C 0.5349(5) 0.0054(5) 0.4485(3) 0.0649(10) Uani 1 1 d . . . C2 C 0.5952(5) 0.0151(5) 0.3587(3) 0.0637(10) Uani 1 1 d . . . C3 C 0.6869(4) 0.0262(4) 0.2500(2) 0.0560(9) Uani 1 1 d . . . C4 C 0.7563(5) -0.1558(4) 0.2136(2) 0.0549(9) Uani 1 1 d . . . C5 C 0.9310(5) -0.1901(5) 0.1610(3) 0.0660(11) Uani 1 1 d . . . H5 H 1.0101 -0.1031 0.1497 0.079 Uiso 1 1 calc R . . C6 C 0.9880(5) -0.3554(5) 0.1251(3) 0.0720(12) Uani 1 1 d . . . H6 H 1.1051 -0.3781 0.0899 0.086 Uiso 1 1 calc R . . C7 C 0.8737(6) -0.4829(5) 0.1411(3) 0.0717(12) Uani 1 1 d . . . H7 H 0.9129 -0.5927 0.1171 0.086 Uiso 1 1 calc R . . C8 C 0.6990(6) -0.4504(5) 0.1929(3) 0.0725(12) Uani 1 1 d . . . H8 H 0.6206 -0.5380 0.2034 0.087 Uiso 1 1 calc R . . C9 C 0.6415(5) -0.2877(5) 0.2291(3) 0.0657(11) Uani 1 1 d . . . H9 H 0.5241 -0.2664 0.2642 0.079 Uiso 1 1 calc R . . C10 C 0.5643(5) 0.1014(4) 0.1845(3) 0.0548(9) Uani 1 1 d . . . C11 C 0.6389(5) 0.1437(5) 0.0827(3) 0.0649(11) Uani 1 1 d . . . H11 H 0.7601 0.1218 0.0562 0.078 Uiso 1 1 calc R . . C12 C 0.5335(6) 0.2175(6) 0.0218(3) 0.0748(12) Uani 1 1 d . . . H12 H 0.5845 0.2480 -0.0451 0.090 Uiso 1 1 calc R . . C13 C 0.3551(6) 0.2464(6) 0.0584(4) 0.0819(13) Uani 1 1 d . . . H13 H 0.2848 0.2962 0.0166 0.098 Uiso 1 1 calc R . . C14 C 0.2794(6) 0.2022(6) 0.1567(4) 0.0853(14) Uani 1 1 d . . . H14 H 0.1574 0.2213 0.1814 0.102 Uiso 1 1 calc R . . C15 C 0.3821(5) 0.1298(5) 0.2193(3) 0.0716(12) Uani 1 1 d . . . H15 H 0.3288 0.0994 0.2859 0.086 Uiso 1 1 calc R . . O2 O 0.0198(4) 0.8541(4) 0.6022(2) 0.0994(12) Uani 1 1 d D . . N1 N 0.0243(7) 0.7336(5) 0.4529(2) 0.1292(19) Uani 1 1 d D . . H1N1 H -0.104(10) 0.822(9) 0.435(6) 0.155 Uiso 1 1 d . . . C16 C 0.0459(6) 0.7254(4) 0.5478(2) 0.0940(15) Uani 1 1 d D . . C17 C 0.1034(8) 0.5504(5) 0.5845(3) 0.131(2) Uani 1 1 d D . . H17 H 0.1466 0.5624 0.6465 0.157 Uiso 1 1 calc R . . C18 C 0.2499(7) 0.4755(7) 0.5029(5) 0.159(3) Uani 1 1 d D . . H18 H 0.3512 0.4214 0.5187 0.191 Uiso 1 1 calc R . . C19 C 0.2339(7) 0.4870(7) 0.4082(4) 0.142(3) Uani 1 1 d D . . H19 H 0.3220 0.4427 0.3547 0.171 Uiso 1 1 calc R . . C20 C 0.0648(10) 0.5759(6) 0.3919(3) 0.153(3) Uani 1 1 d D . . H20 H 0.0853 0.6114 0.3201 0.183 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 0.0769(17) 0.0661(17) 0.0616(17) -0.0023(12) -0.0178(13) -0.0084(12) C1 0.081(2) 0.063(2) 0.0471(19) -0.0046(15) -0.0100(16) 0.0086(17) C2 0.075(2) 0.063(2) 0.050(2) -0.0044(16) -0.0104(16) 0.0073(17) C3 0.064(2) 0.057(2) 0.0434(18) -0.0039(14) -0.0054(14) 0.0001(15) C4 0.070(2) 0.0538(19) 0.0374(17) 0.0008(13) -0.0082(14) 0.0073(15) C5 0.066(2) 0.065(2) 0.061(2) -0.0051(17) -0.0045(16) 0.0014(16) C6 0.074(2) 0.075(3) 0.059(2) -0.0062(18) -0.0037(18) 0.017(2) C7 0.096(3) 0.060(2) 0.054(2) -0.0048(17) -0.0134(19) 0.018(2) C8 0.089(3) 0.056(2) 0.068(2) 0.0004(18) -0.011(2) 0.0029(18) C9 0.070(2) 0.064(2) 0.058(2) -0.0013(17) -0.0047(17) 0.0032(17) C10 0.067(2) 0.0474(18) 0.0459(18) -0.0018(13) -0.0074(14) 0.0035(14) C11 0.067(2) 0.075(2) 0.049(2) -0.0023(17) -0.0093(16) 0.0033(17) C12 0.089(3) 0.078(3) 0.057(2) 0.0041(19) -0.018(2) -0.002(2) C13 0.086(3) 0.086(3) 0.078(3) 0.003(2) -0.033(2) 0.010(2) C14 0.074(3) 0.100(3) 0.077(3) -0.001(2) -0.014(2) 0.020(2) C15 0.072(2) 0.078(3) 0.058(2) 0.0044(18) -0.0041(17) 0.0078(18) O2 0.108(2) 0.126(3) 0.069(2) -0.0088(19) -0.0308(17) 0.005(2) N1 0.168(5) 0.161(5) 0.062(3) -0.013(3) -0.040(3) 0.021(4) C16 0.097(3) 0.124(4) 0.064(3) -0.011(3) -0.028(2) 0.009(3) C17 0.160(6) 0.154(6) 0.091(4) -0.016(4) -0.068(4) 0.044(5) C18 0.120(5) 0.192(8) 0.175(8) -0.077(7) -0.053(5) 0.030(5) C19 0.111(5) 0.144(6) 0.145(7) -0.039(5) 0.036(4) -0.029(4) C20 0.265(11) 0.136(6) 0.059(3) -0.007(3) -0.041(5) -0.006(7) _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 C3 1.424(4) . ? O1 H1O1 0.91(5) . ? C1 C2 1.197(5) . ? C1 C1 1.375(7) 2_656 ? C2 C3 1.481(5) . ? C3 C10 1.518(5) . ? C3 C4 1.535(5) . ? C4 C9 1.384(5) . ? C4 C5 1.388(5) . ? C5 C6 1.397(5) . ? C5 H5 0.9300 . ? C6 C7 1.354(6) . ? C6 H6 0.9300 . ? C7 C8 1.383(6) . ? C7 H7 0.9300 . ? C8 C9 1.380(5) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C15 1.385(5) . ? C10 C11 1.402(5) . ? C11 C12 1.373(6) . ? C11 H11 0.9300 . ? C12 C13 1.361(6) . ? C12 H12 0.9300 . ? C13 C14 1.367(7) . ? C13 H13 0.9300 . ? C14 C15 1.373(6) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? O2 C16 1.240(2) . ? N1 C16 1.330(2) . ? N1 C20 1.477(2) . ? N1 H1N1 1.23(8) . ? C16 C17 1.508(2) . ? C17 C18 1.490(3) . ? C17 C20 1.652(8) 2_566 ? C17 H17 0.9800 . ? C18 C19 1.313(3) . ? C18 H18 0.9300 . ? C19 C20 1.497(3) . ? C19 H19 0.9300 . ? C20 C17 1.652(8) 2_566 ? C20 H20 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 C3 O1 H1O1 114(3) . . ? C2 C1 C1 179.7(6) . 2_656 ? C1 C2 C3 174.5(4) . . ? O1 C3 C2 109.6(3) . . ? O1 C3 C10 106.6(3) . . ? C2 C3 C10 112.2(3) . . ? O1 C3 C4 111.0(3) . . ? C2 C3 C4 108.4(3) . . ? C10 C3 C4 109.0(3) . . ? C9 C4 C5 118.7(3) . . ? C9 C4 C3 119.9(3) . . ? C5 C4 C3 121.3(3) . . ? C4 C5 C6 119.9(4) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C7 C6 C5 120.5(4) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C6 C7 C8 120.2(4) . . ? C6 C7 H7 119.9 . . ? C8 C7 H7 119.9 . . ? C9 C8 C7 119.8(4) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C8 C9 C4 120.9(4) . . ? C8 C9 H9 119.6 . . ? C4 C9 H9 119.6 . . ? C15 C10 C11 117.9(3) . . ? C15 C10 C3 123.7(3) . . ? C11 C10 C3 118.4(3) . . ? C12 C11 C10 120.2(3) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C13 C12 C11 120.7(4) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C12 C13 C14 119.9(4) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C13 C14 C15 120.5(4) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C14 C15 C10 120.7(4) . . ? C14 C15 H15 119.6 . . ? C10 C15 H15 119.6 . . ? C16 N1 C20 118.35(19) . . ? C16 N1 H1N1 118(4) . . ? C20 N1 H1N1 112(3) . . ? O2 C16 N1 121.7(2) . . ? O2 C16 C17 122.5(2) . . ? N1 C16 C17 115.77(17) . . ? C18 C17 C16 107.7(2) . . ? C18 C17 C20 109.8(4) . 2_566 ? C16 C17 C20 110.3(4) . 2_566 ? C18 C17 H17 109.6 . . ? C16 C17 H17 109.6 . . ? C20 C17 H17 109.6 2_566 . ? C19 C18 C17 119.0(2) . . ? C19 C18 H18 120.5 . . ? C17 C18 H18 120.5 . . ? C18 C19 C20 115.8(2) . . ? C18 C19 H19 122.1 . . ? C20 C19 H19 122.1 . . ? N1 C20 C19 109.2(2) . . ? N1 C20 C17 111.9(4) . 2_566 ? C19 C20 C17 112.9(4) . 2_566 ? N1 C20 H20 107.5 . . ? C19 C20 H20 107.5 . . ? C17 C20 H20 107.5 2_566 . ? 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 C1 C1 C2 C3 147(100) 2_656 . . . ? C1 C2 C3 O1 -42(4) . . . . ? C1 C2 C3 C10 -160(4) . . . . ? C1 C2 C3 C4 80(4) . . . . ? O1 C3 C4 C9 173.3(3) . . . . ? C2 C3 C4 C9 52.8(4) . . . . ? C10 C3 C4 C9 -69.6(4) . . . . ? O1 C3 C4 C5 -9.7(4) . . . . ? C2 C3 C4 C5 -130.2(4) . . . . ? C10 C3 C4 C5 107.4(4) . . . . ? C9 C4 C5 C6 -0.2(5) . . . . ? C3 C4 C5 C6 -177.2(3) . . . . ? C4 C5 C6 C7 0.1(6) . . . . ? C5 C6 C7 C8 0.3(6) . . . . ? C6 C7 C8 C9 -0.5(6) . . . . ? C7 C8 C9 C4 0.3(6) . . . . ? C5 C4 C9 C8 0.0(6) . . . . ? C3 C4 C9 C8 177.0(3) . . . . ? O1 C3 C10 C15 -129.9(4) . . . . ? C2 C3 C10 C15 -9.9(5) . . . . ? C4 C3 C10 C15 110.2(4) . . . . ? O1 C3 C10 C11 50.5(4) . . . . ? C2 C3 C10 C11 170.5(3) . . . . ? C4 C3 C10 C11 -69.3(4) . . . . ? C15 C10 C11 C12 2.6(5) . . . . ? C3 C10 C11 C12 -177.8(3) . . . . ? C10 C11 C12 C13 -1.7(6) . . . . ? C11 C12 C13 C14 0.1(7) . . . . ? C12 C13 C14 C15 0.5(7) . . . . ? C13 C14 C15 C10 0.5(7) . . . . ? C11 C10 C15 C14 -2.1(6) . . . . ? C3 C10 C15 C14 178.4(4) . . . . ? C20 N1 C16 O2 177.7(5) . . . . ? C20 N1 C16 C17 -2.5(7) . . . . ? O2 C16 C17 C18 -134.7(4) . . . . ? N1 C16 C17 C18 45.5(5) . . . . ? O2 C16 C17 C20 105.4(5) . . . 2_566 ? N1 C16 C17 C20 -74.4(5) . . . 2_566 ? C16 C17 C18 C19 -44.5(6) . . . . ? C20 C17 C18 C19 75.7(6) 2_566 . . . ? C17 C18 C19 C20 -0.3(7) . . . . ? C16 N1 C20 C19 -43.0(6) . . . . ? C16 N1 C20 C17 82.9(5) . . . 2_566 ? C18 C19 C20 N1 44.4(6) . . . . ? C18 C19 C20 C17 -80.9(5) . . . 2_566 ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.380 _refine_diff_density_min -0.258 _refine_diff_density_rms 0.061 # Attachment '1-b(water diffused out).cif' data_pyr102rest1 _database_code_depnum_ccdc_archive 'CCDC 603859' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,1,6,6-tetraphenyl-2,4- hexadiyne-1,6-diol (3,7-Diazatricyclo[4.2.2.22,5]dodeca-9,11-diene-4,8-dione) clathrate ; _chemical_name_common ; 1,1,6,6-tetraphenyl-2,4- hexadiyne-1,6-diol (3,7- Diazatricyclo(4.2.2.22,5)dodeca-9,11-diene-4,8-dione) clathrate ; _chemical_melting_point ? _chemical_formula_moiety '(C30 H22 O2), (C10 H10 N2 O2)' _chemical_formula_sum 'C20 H16 N O2' _chemical_formula_weight 302.34 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 6.151(6) _cell_length_b 9.114(11) _cell_length_c 13.112(2) _cell_angle_alpha 95.93(5) _cell_angle_beta 93.28(5) _cell_angle_gamma 100.18(6) _cell_volume 717.5(16) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 399 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 25.08 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.399 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 318 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9734 _exptl_absorpt_correction_T_max 0.9910 _exptl_absorpt_process_details none _exptl_special_details ; ? ; _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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 5895 _diffrn_reflns_av_R_equivalents 0.110 _diffrn_reflns_av_sigmaI/netI 0.107 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 25.08 _reflns_number_total 1463 _reflns_number_gt 769 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1463 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2102 _refine_ls_R_factor_gt 0.1324 _refine_ls_wR_factor_ref 0.4203 _refine_ls_wR_factor_gt 0.3794 _refine_ls_goodness_of_fit_ref 1.485 _refine_ls_restrained_S_all 1.485 _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 0.4623(12) 0.5237(8) 0.7228(5) 0.091(2) Uani 1 1 d . . . H1O1 H 0.4713 0.4361 0.7285 0.136 Uiso 1 1 calc R . . C1 C 0.054(2) 0.5082(11) 0.5482(8) 0.093(3) Uani 1 1 d . . . C2 C 0.138(2) 0.5216(12) 0.6321(8) 0.091(3) Uani 1 1 d . . . C3 C 0.2468(17) 0.5433(12) 0.7338(7) 0.077(3) Uani 1 1 d . . . C4 C 0.137(2) 0.4508(12) 0.8051(8) 0.086(3) Uani 1 1 d . . . C5 C 0.249(2) 0.4330(14) 0.8955(8) 0.093(3) Uani 1 1 d . . . H5 H 0.3977 0.4764 0.9095 0.112 Uiso 1 1 calc R . . C6 C 0.141(3) 0.3519(14) 0.9637(9) 0.103(4) Uani 1 1 d . . . H6 H 0.2144 0.3439 1.0262 0.124 Uiso 1 1 calc R . . C7 C -0.070(3) 0.2830(16) 0.9434(9) 0.111(5) Uani 1 1 d . . . H7 H -0.1398 0.2280 0.9922 0.134 Uiso 1 1 calc R . . C8 C -0.184(2) 0.2913(14) 0.8537(10) 0.109(4) Uani 1 1 d . . . H8 H -0.3304 0.2434 0.8386 0.131 Uiso 1 1 calc R . . C9 C -0.070(2) 0.3744(13) 0.7870(8) 0.091(3) Uani 1 1 d . . . H9 H -0.1429 0.3784 0.7234 0.109 Uiso 1 1 calc R . . C10 C 0.2555(19) 0.7045(11) 0.7761(7) 0.077(3) Uani 1 1 d . . . C11 C 0.071(2) 0.7627(12) 0.7745(7) 0.092(3) Uani 1 1 d . . . H11 H -0.0614 0.7038 0.7451 0.111 Uiso 1 1 calc R . . C12 C 0.072(2) 0.9126(13) 0.8168(9) 0.097(4) Uani 1 1 d . . . H12 H -0.0554 0.9542 0.8125 0.117 Uiso 1 1 calc R . . C13 C 0.257(3) 0.9899(11) 0.8617(9) 0.098(4) Uani 1 1 d . . . H13 H 0.2578 1.0858 0.8940 0.118 Uiso 1 1 calc R . . C14 C 0.448(3) 0.9358(12) 0.8633(8) 0.101(4) Uani 1 1 d . . . H14 H 0.5796 0.9967 0.8912 0.122 Uiso 1 1 calc R . . C15 C 0.445(2) 0.7869(11) 0.8224(8) 0.088(3) Uani 1 1 d . . . H15 H 0.5725 0.7458 0.8274 0.106 Uiso 1 1 calc R . . O2 O 0.4232(15) 1.2290(10) 0.6717(7) 0.116(3) Uani 1 1 d . . . N1 N 0.3036(17) 1.0029(11) 0.5994(7) 0.096(3) Uani 1 1 d . . . H1 H 0.2509 0.9767 0.6555 0.116 Uiso 1 1 d R . . C16 C 0.4035(19) 1.1408(15) 0.5958(9) 0.090(3) Uani 1 1 d . . . C17 C 0.493(2) 1.1697(14) 0.4977(10) 0.102(4) Uani 1 1 d . . . H17 H 0.5275 1.2784 0.4953 0.123 Uiso 1 1 d R . . C18 C 0.331(3) 1.1048(18) 0.4163(10) 0.112(4) Uani 1 1 d . . . H18 H 0.2964 1.1580 0.3627 0.135 Uiso 1 1 d R . . C19 C 0.235(3) 0.972(2) 0.4187(9) 0.113(4) Uani 1 1 d . . . H19 H 0.1361 0.9223 0.3643 0.135 Uiso 1 1 d R . . C20 C 0.283(2) 0.8975(16) 0.5065(10) 0.105(4) Uani 1 1 d . . . H20 H 0.1595 0.8153 0.5118 0.126 Uiso 1 1 d 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 0.073(5) 0.095(5) 0.100(5) 0.004(4) 0.003(4) 0.012(4) C1 0.125(10) 0.077(7) 0.066(6) 0.006(6) 0.003(6) -0.008(7) C2 0.106(9) 0.084(7) 0.074(7) -0.007(5) 0.006(6) 0.008(6) C3 0.069(6) 0.092(7) 0.066(5) -0.001(5) -0.003(4) 0.014(5) C4 0.107(9) 0.074(6) 0.074(6) 0.011(5) 0.001(6) 0.013(7) C5 0.101(8) 0.095(8) 0.075(6) -0.005(6) -0.012(6) 0.009(7) C6 0.135(13) 0.082(7) 0.087(8) 0.021(6) -0.017(8) 0.006(8) C7 0.153(15) 0.113(10) 0.080(8) 0.017(7) 0.014(8) 0.050(11) C8 0.126(11) 0.089(8) 0.102(9) 0.006(7) 0.009(8) -0.006(8) C9 0.104(9) 0.095(8) 0.066(6) 0.010(6) -0.003(6) -0.002(7) C10 0.085(8) 0.069(6) 0.073(6) 0.002(5) 0.008(5) 0.008(6) C11 0.121(10) 0.089(7) 0.065(6) 0.001(5) 0.004(5) 0.020(8) C12 0.112(10) 0.080(7) 0.101(7) 0.011(6) 0.003(7) 0.025(8) C13 0.136(12) 0.052(6) 0.103(8) 0.000(5) 0.001(8) 0.018(7) C14 0.134(11) 0.060(6) 0.098(8) 0.009(5) 0.001(7) -0.015(7) C15 0.104(9) 0.068(6) 0.088(7) 0.007(5) 0.000(6) 0.009(6) O2 0.114(7) 0.106(6) 0.118(6) -0.017(5) 0.007(5) 0.011(5) N1 0.103(7) 0.094(7) 0.094(6) 0.007(5) 0.012(5) 0.026(6) C16 0.085(8) 0.084(7) 0.095(8) 0.000(6) 0.006(6) 0.007(6) C17 0.124(11) 0.081(7) 0.103(8) 0.009(6) 0.002(8) 0.027(7) C18 0.121(12) 0.110(10) 0.112(10) 0.030(8) 0.009(9) 0.027(9) C19 0.118(11) 0.136(13) 0.075(7) -0.005(8) -0.017(7) 0.018(10) C20 0.074(7) 0.106(9) 0.121(9) -0.025(8) 0.011(6) -0.004(7) _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 C3 1.382(12) . ? O1 H1O1 0.8200 . ? C1 C2 1.173(13) . ? C1 C1 1.38(2) 2_566 ? C2 C3 1.436(14) . ? C3 C4 1.441(16) . ? C3 C10 1.507(14) . ? C4 C9 1.336(17) . ? C4 C5 1.375(16) . ? C5 C6 1.348(18) . ? C5 H5 0.9300 . ? C6 C7 1.335(18) . ? C6 H6 0.9300 . ? C7 C8 1.350(17) . ? C7 H7 0.9300 . ? C8 C9 1.359(17) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.337(16) . ? C10 C15 1.344(15) . ? C11 C12 1.419(15) . ? C11 H11 0.9300 . ? C12 C13 1.301(17) . ? C12 H12 0.9300 . ? C13 C14 1.350(18) . ? C13 H13 0.9300 . ? C14 C15 1.403(15) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? O2 C16 1.199(13) . ? N1 C16 1.304(16) . ? N1 C20 1.457(14) . ? N1 H1 0.8600 . ? C16 C17 1.458(18) . ? C17 C18 1.420(19) . ? C17 C20 1.606(18) 2_676 ? C17 H17 0.9800 . ? C18 C19 1.257(19) . ? C18 H18 0.9300 . ? C19 C20 1.44(2) . ? C19 H19 0.9300 . ? C20 C17 1.606(18) 2_676 ? C20 H20 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 C3 O1 H1O1 109.5 . . ? C2 C1 C1 176.9(17) . 2_566 ? C1 C2 C3 177.5(12) . . ? O1 C3 C2 106.7(8) . . ? O1 C3 C4 112.9(9) . . ? C2 C3 C4 114.7(10) . . ? O1 C3 C10 107.4(9) . . ? C2 C3 C10 107.5(9) . . ? C4 C3 C10 107.3(8) . . ? C9 C4 C5 116.6(11) . . ? C9 C4 C3 123.3(10) . . ? C5 C4 C3 120.1(12) . . ? C6 C5 C4 119.3(13) . . ? C6 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? C7 C6 C5 121.5(12) . . ? C7 C6 H6 119.2 . . ? C5 C6 H6 119.2 . . ? C6 C7 C8 121.4(14) . . ? C6 C7 H7 119.3 . . ? C8 C7 H7 119.3 . . ? C7 C8 C9 115.6(14) . . ? C7 C8 H8 122.2 . . ? C9 C8 H8 122.2 . . ? C4 C9 C8 125.4(12) . . ? C4 C9 H9 117.3 . . ? C8 C9 H9 117.3 . . ? C11 C10 C15 119.6(10) . . ? C11 C10 C3 120.0(11) . . ? C15 C10 C3 120.2(10) . . ? C10 C11 C12 121.4(12) . . ? C10 C11 H11 119.3 . . ? C12 C11 H11 119.3 . . ? C13 C12 C11 117.9(12) . . ? C13 C12 H12 121.1 . . ? C11 C12 H12 121.1 . . ? C12 C13 C14 122.4(10) . . ? C12 C13 H13 118.8 . . ? C14 C13 H13 118.8 . . ? C13 C14 C15 119.4(12) . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? C10 C15 C14 119.2(12) . . ? C10 C15 H15 120.4 . . ? C14 C15 H15 120.4 . . ? C16 N1 C20 118.2(11) . . ? C16 N1 H1 120.0 . . ? C20 N1 H1 121.8 . . ? O2 C16 N1 119.2(12) . . ? O2 C16 C17 126.0(12) . . ? N1 C16 C17 114.7(10) . . ? C18 C17 C16 109.4(13) . . ? C18 C17 C20 113.3(10) . 2_676 ? C16 C17 C20 107.0(10) . 2_676 ? C18 C17 H17 108.9 . . ? C16 C17 H17 108.9 . . ? C20 C17 H17 109.4 2_676 . ? C19 C18 C17 117.8(13) . . ? C19 C18 H18 120.4 . . ? C17 C18 H18 121.8 . . ? C18 C19 C20 118.3(13) . . ? C18 C19 H19 120.6 . . ? C20 C19 H19 121.1 . . ? C19 C20 N1 109.5(11) . . ? C19 C20 C17 114.1(11) . 2_676 ? N1 C20 C17 107.9(10) . 2_676 ? C19 C20 H20 108.6 . . ? N1 C20 H20 108.2 . . ? C17 C20 H20 108.5 2_676 . ? 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 C1 C1 C2 C3 -136(26) 2_566 . . . ? C1 C2 C3 O1 -59(28) . . . . ? C1 C2 C3 C4 175(28) . . . . ? C1 C2 C3 C10 56(28) . . . . ? O1 C3 C4 C9 -136.0(11) . . . . ? C2 C3 C4 C9 -13.5(15) . . . . ? C10 C3 C4 C9 105.9(12) . . . . ? O1 C3 C4 C5 41.4(13) . . . . ? C2 C3 C4 C5 163.9(10) . . . . ? C10 C3 C4 C5 -76.8(12) . . . . ? C9 C4 C5 C6 -5.6(16) . . . . ? C3 C4 C5 C6 176.9(11) . . . . ? C4 C5 C6 C7 3.0(19) . . . . ? C5 C6 C7 C8 0(2) . . . . ? C6 C7 C8 C9 -0.3(18) . . . . ? C5 C4 C9 C8 5.7(18) . . . . ? C3 C4 C9 C8 -176.9(11) . . . . ? C7 C8 C9 C4 -2.7(19) . . . . ? O1 C3 C10 C11 166.2(9) . . . . ? C2 C3 C10 C11 51.7(13) . . . . ? C4 C3 C10 C11 -72.2(13) . . . . ? O1 C3 C10 C15 -18.8(13) . . . . ? C2 C3 C10 C15 -133.2(11) . . . . ? C4 C3 C10 C15 102.9(12) . . . . ? C15 C10 C11 C12 2.8(17) . . . . ? C3 C10 C11 C12 177.9(9) . . . . ? C10 C11 C12 C13 -3.2(18) . . . . ? C11 C12 C13 C14 4.4(19) . . . . ? C12 C13 C14 C15 -5.2(19) . . . . ? C11 C10 C15 C14 -3.5(17) . . . . ? C3 C10 C15 C14 -178.6(9) . . . . ? C13 C14 C15 C10 4.6(17) . . . . ? C20 N1 C16 O2 -179.5(10) . . . . ? C20 N1 C16 C17 -2.7(16) . . . . ? O2 C16 C17 C18 -137.6(13) . . . . ? N1 C16 C17 C18 45.9(14) . . . . ? O2 C16 C17 C20 99.4(14) . . . 2_676 ? N1 C16 C17 C20 -77.1(13) . . . 2_676 ? C16 C17 C18 C19 -47.6(17) . . . . ? C20 C17 C18 C19 71.6(19) 2_676 . . . ? C17 C18 C19 C20 4(2) . . . . ? C18 C19 C20 N1 39.6(17) . . . . ? C18 C19 C20 C17 -81.3(16) . . . 2_676 ? C16 N1 C20 C19 -39.6(15) . . . . ? C16 N1 C20 C17 85.0(14) . . . 2_676 ? _diffrn_measured_fraction_theta_max 0.575 _diffrn_reflns_theta_full 25.08 _diffrn_measured_fraction_theta_full 0.575 _refine_diff_density_max 0.224 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.059 # Attachment '1-b.cif' data_r13 _database_code_depnum_ccdc_archive 'CCDC 603860' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; 1,1,6,6-tetraphenyl-2,4- hexadiyne-1,6-diol(3,7- Diazatricyclo(4.2.2.22,5) dodeca-9,11-diene-4,8-dione)water clathrate ; _chemical_melting_point ? _chemical_formula_moiety '1.5(C30 H22 O2), 1.5(C10 H10 N2 O2), H2O' _chemical_formula_sum 'C60 H50 N3 O7' _chemical_formula_weight 925.03 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.555(2) _cell_length_b 13.574(3) _cell_length_c 17.197(3) _cell_angle_alpha 81.04(2) _cell_angle_beta 80.96(2) _cell_angle_gamma 81.74(2) _cell_volume 2385.6(8) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.288 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 974 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9751 _exptl_absorpt_correction_T_max 0.9916 _exptl_absorpt_process_details none _exptl_special_details ; ? ; _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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 95 _diffrn_standards_number none _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 11285 _diffrn_reflns_av_R_equivalents 0.0986 _diffrn_reflns_av_sigmaI/netI 0.1533 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.21 _diffrn_reflns_theta_max 22.25 _reflns_number_total 5149 _reflns_number_gt 1744 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_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^)+(0.1645P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5149 _refine_ls_number_parameters 627 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2164 _refine_ls_R_factor_gt 0.1003 _refine_ls_wR_factor_ref 0.2969 _refine_ls_wR_factor_gt 0.2628 _refine_ls_goodness_of_fit_ref 0.870 _refine_ls_restrained_S_all 0.870 _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 O1A O 0.4431(5) 0.2508(3) 0.3461(3) 0.0705(16) Uani 1 1 d . . . H1OA H 0.3746 0.2402 0.3340 0.106 Uiso 1 1 calc R . . C1A C 0.4896(8) 0.0517(6) 0.4872(5) 0.077(3) Uani 1 1 d . . . C2A C 0.4649(7) 0.1392(7) 0.4647(5) 0.071(3) Uani 1 1 d . . . C3A C 0.4329(8) 0.2440(6) 0.4301(6) 0.063(2) Uani 1 1 d . . . C4A C 0.2977(8) 0.2843(5) 0.4691(6) 0.063(2) Uani 1 1 d . . . C5A C 0.2071(9) 0.3308(6) 0.4234(5) 0.072(2) Uani 1 1 d . . . H5A H 0.2253 0.3363 0.3683 0.086 Uiso 1 1 calc R . . C6A C 0.0857(9) 0.3708(6) 0.4594(7) 0.086(3) Uani 1 1 d . . . H6A H 0.0228 0.4014 0.4281 0.103 Uiso 1 1 calc R . . C7A C 0.0597(9) 0.3646(6) 0.5406(7) 0.084(3) Uani 1 1 d . . . H7A H -0.0200 0.3922 0.5644 0.101 Uiso 1 1 calc R . . C8A C 0.1511(9) 0.3180(6) 0.5863(5) 0.078(3) Uani 1 1 d . . . H8A H 0.1340 0.3127 0.6414 0.094 Uiso 1 1 calc R . . C9A C 0.2701(8) 0.2787(6) 0.5496(6) 0.074(3) Uani 1 1 d . . . H9A H 0.3327 0.2476 0.5808 0.089 Uiso 1 1 calc R . . C10A C 0.5278(8) 0.3126(6) 0.4435(5) 0.068(2) Uani 1 1 d . . . C11A C 0.5248(7) 0.4126(6) 0.4054(5) 0.073(2) Uani 1 1 d . . . H11A H 0.4610 0.4383 0.3734 0.087 Uiso 1 1 calc R . . C12A C 0.6127(9) 0.4724(6) 0.4143(6) 0.090(3) Uani 1 1 d . . . H12A H 0.6101 0.5372 0.3868 0.108 Uiso 1 1 calc R . . C13A C 0.7039(9) 0.4392(8) 0.4624(6) 0.100(3) Uani 1 1 d . . . H13A H 0.7644 0.4806 0.4672 0.120 Uiso 1 1 calc R . . C14A C 0.7070(9) 0.3451(8) 0.5037(6) 0.096(3) Uani 1 1 d . . . H14A H 0.7673 0.3230 0.5386 0.115 Uiso 1 1 calc R . . C15A C 0.6198(9) 0.2820(6) 0.4935(6) 0.083(3) Uani 1 1 d . . . H15A H 0.6239 0.2173 0.5212 0.099 Uiso 1 1 calc R . . O2A O 0.8036(6) 0.1164(4) 0.6202(3) 0.0867(18) Uani 1 1 d . . . N1A N 0.8861(7) -0.0371(6) 0.5931(4) 0.095(2) Uani 1 1 d . . . H1NA H 0.8197 -0.0626 0.6197 0.114 Uiso 1 1 calc R . . C16A C 0.8900(10) 0.0611(7) 0.5878(6) 0.081(3) Uani 1 1 d . . . C17A C 1.0149(10) 0.0927(7) 0.5416(7) 0.091(3) Uani 1 1 d . . . H17A H 1.0268 0.1581 0.5549 0.110 Uiso 1 1 calc R . . C18A C 1.1267(10) 0.0173(10) 0.5638(6) 0.106(3) Uani 1 1 d . . . H18A H 1.2026 0.0379 0.5731 0.127 Uiso 1 1 calc R . . C19A C 1.1140(10) -0.0770(8) 0.5697(6) 0.092(3) Uani 1 1 d . . . H19A H 1.1807 -0.1263 0.5834 0.111 Uiso 1 1 calc R . . C20A C 0.9926(11) -0.1037(7) 0.5543(7) 0.097(3) Uani 1 1 d . . . H20A H 0.9845 -0.1735 0.5779 0.117 Uiso 1 1 calc R . . O1B O 0.0159(6) 1.2090(4) 0.0163(4) 0.117(2) Uani 1 1 d . . . H1OB H 0.0757 1.2340 -0.0128 0.175 Uiso 1 1 calc R . . C1B C 0.0780(8) 1.0209(7) 0.1616(6) 0.094(3) Uani 1 1 d . . . C2B C 0.0613(8) 1.1104(7) 0.1357(6) 0.091(3) Uani 1 1 d . . . C3B C 0.0273(10) 1.2132(6) 0.0963(6) 0.081(3) Uani 1 1 d . . . C4B C -0.1070(8) 1.2530(6) 0.1361(6) 0.071(3) Uani 1 1 d . . . C5B C -0.1953(10) 1.3088(6) 0.0896(6) 0.087(3) Uani 1 1 d . . . H5B H -0.1745 1.3187 0.0346 0.104 Uiso 1 1 calc R . . C6B C -0.3151(10) 1.3500(6) 0.1248(7) 0.085(3) Uani 1 1 d . . . H6B H -0.3752 1.3848 0.0931 0.102 Uiso 1 1 calc R . . C7B C -0.3450(9) 1.3398(6) 0.2055(8) 0.092(3) Uani 1 1 d . . . H7B H -0.4244 1.3684 0.2290 0.110 Uiso 1 1 calc R . . C8B C -0.2558(10) 1.2865(7) 0.2517(6) 0.094(3) Uani 1 1 d . . . H8B H -0.2751 1.2797 0.3068 0.113 Uiso 1 1 calc R . . C9B C -0.1380(10) 1.2429(6) 0.2170(7) 0.090(3) Uani 1 1 d . . . H9B H -0.0794 1.2064 0.2491 0.108 Uiso 1 1 calc R . . C10B C 0.1232(11) 1.2819(7) 0.1077(7) 0.090(3) Uani 1 1 d . . . C11B C 0.1247(11) 1.3718(10) 0.0558(6) 0.112(4) Uani 1 1 d . . . H11B H 0.0708 1.3862 0.0166 0.135 Uiso 1 1 calc R . . C12B C 0.2093(13) 1.4406(9) 0.0634(8) 0.124(4) Uani 1 1 d . . . H12B H 0.2094 1.5019 0.0306 0.149 Uiso 1 1 calc R . . C13B C 0.2915(10) 1.4155(8) 0.1201(8) 0.114(4) Uani 1 1 d . . . H13B H 0.3481 1.4598 0.1253 0.137 Uiso 1 1 calc R . . C14B C 0.2905(10) 1.3263(9) 0.1684(7) 0.116(4) Uani 1 1 d . . . H14B H 0.3470 1.3101 0.2061 0.139 Uiso 1 1 calc R . . C15B C 0.2054(11) 1.2580(7) 0.1622(6) 0.096(3) Uani 1 1 d . . . H15B H 0.2057 1.1970 0.1955 0.115 Uiso 1 1 calc R . . O2B O 0.6408(6) -0.0946(4) 0.6976(3) 0.093(2) Uani 1 1 d . . . N1B N 0.5650(8) 0.0606(6) 0.7326(5) 0.124(3) Uani 1 1 d . . . H1NB H 0.6369 0.0839 0.7139 0.149 Uiso 1 1 calc R . . C16B C 0.5516(13) -0.0369(8) 0.7306(6) 0.093(3) Uani 1 1 d . . . C17B C 0.4237(13) -0.0663(8) 0.7675(9) 0.119(4) Uani 1 1 d . . . H17B H 0.4105 -0.1283 0.7489 0.143 Uiso 1 1 calc R . . C18B C 0.3205(15) 0.0093(15) 0.7506(8) 0.154(5) Uani 1 1 d . . . H18B H 0.2419 -0.0090 0.7436 0.185 Uiso 1 1 calc R . . C19B C 0.3343(13) 0.1045(14) 0.7448(7) 0.136(6) Uani 1 1 d . . . H19B H 0.2721 0.1551 0.7269 0.164 Uiso 1 1 calc R . . C20B C 0.4526(15) 0.1263(7) 0.7679(10) 0.136(5) Uani 1 1 d . . . H20B H 0.4641 0.1967 0.7485 0.163 Uiso 1 1 calc R . . O1C O 0.1678(5) 0.7120(4) 0.3220(3) 0.0878(18) Uani 1 1 d . . . H1OC H 0.1311 0.7626 0.3402 0.132 Uiso 1 1 calc R . . C1C C 0.1043(8) 0.9196(7) 0.1885(5) 0.085(3) Uani 1 1 d . . . C2C C 0.1304(8) 0.8323(6) 0.2084(5) 0.082(3) Uani 1 1 d . . . C3C C 0.1626(9) 0.7245(6) 0.2376(6) 0.078(3) Uani 1 1 d . . . C4C C 0.2978(9) 0.6903(6) 0.1952(7) 0.075(3) Uani 1 1 d . . . C5C C 0.3943(9) 0.6379(6) 0.2355(6) 0.090(3) Uani 1 1 d . . . H5C H 0.3791 0.6252 0.2907 0.109 Uiso 1 1 calc R . . C6C C 0.5134(11) 0.6036(7) 0.1966(8) 0.102(4) Uani 1 1 d . . . H6C H 0.5771 0.5684 0.2254 0.123 Uiso 1 1 calc R . . C7C C 0.5375(10) 0.6217(7) 0.1149(9) 0.105(4) Uani 1 1 d . . . H7C H 0.6179 0.5986 0.0892 0.126 Uiso 1 1 calc R . . C8C C 0.4471(12) 0.6723(7) 0.0715(6) 0.102(3) Uani 1 1 d . . . H8C H 0.4648 0.6841 0.0164 0.122 Uiso 1 1 calc R . . C9C C 0.3259(11) 0.7067(6) 0.1107(7) 0.090(3) Uani 1 1 d . . . H9C H 0.2628 0.7409 0.0810 0.107 Uiso 1 1 calc R . . C10C C 0.0642(8) 0.6595(6) 0.2225(5) 0.070(2) Uani 1 1 d . . . C11C C 0.0804(9) 0.5614(6) 0.2566(6) 0.093(3) Uani 1 1 d . . . H11C H 0.1480 0.5370 0.2859 0.111 Uiso 1 1 calc R . . C12C C -0.0079(10) 0.4993(7) 0.2459(6) 0.093(3) Uani 1 1 d . . . H12C H 0.0008 0.4326 0.2692 0.111 Uiso 1 1 calc R . . C13C C -0.1100(10) 0.5344(9) 0.2009(6) 0.106(3) Uani 1 1 d . . . H13C H -0.1682 0.4925 0.1934 0.127 Uiso 1 1 calc R . . C14C C -0.1186(10) 0.6343(9) 0.1686(6) 0.110(3) Uani 1 1 d . . . H14C H -0.1846 0.6603 0.1384 0.132 Uiso 1 1 calc R . . C15C C -0.0327(10) 0.6973(7) 0.1795(5) 0.091(3) Uani 1 1 d . . . H15C H -0.0416 0.7646 0.1576 0.109 Uiso 1 1 calc R . . O2C O 0.2403(8) 0.1366(6) 0.9352(4) 0.158(3) Uani 1 1 d . . . N1C N 0.3103(10) -0.0203(8) 0.9030(6) 0.138(4) Uani 1 1 d . . . H1NC H 0.2389 -0.0434 0.9233 0.165 Uiso 1 1 calc R . . C16C C 0.3235(14) 0.0762(10) 0.9054(6) 0.114(4) Uani 1 1 d . . . C17C C 0.4543(15) 0.1053(9) 0.8663(9) 0.134(4) Uani 1 1 d . . . H17C H 0.4697 0.1667 0.8848 0.160 Uiso 1 1 calc R . . C18C C 0.5560(12) 0.0235(14) 0.8866(8) 0.154(5) Uani 1 1 d . . . H18C H 0.6345 0.0385 0.8969 0.185 Uiso 1 1 calc R . . C19C C 0.5376(16) -0.0665(12) 0.8901(7) 0.132(5) Uani 1 1 d . . . H19C H 0.5982 -0.1191 0.9068 0.159 Uiso 1 1 calc R . . C20C C 0.4156(17) -0.0852(9) 0.8665(9) 0.140(5) Uani 1 1 d . . . H20C H 0.4018 -0.1552 0.8858 0.168 Uiso 1 1 calc R . . O1W O 0.100(2) -0.0706(18) 1.0068(14) 0.208(15) Uiso 0.394(18) 1 d P . . 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 O1A 0.075(4) 0.060(4) 0.078(4) -0.022(3) -0.002(3) -0.010(3) C1A 0.076(6) 0.057(6) 0.095(7) -0.011(6) -0.012(5) 0.000(6) C2A 0.073(6) 0.051(6) 0.088(6) -0.013(5) -0.012(5) 0.004(5) C3A 0.054(6) 0.043(6) 0.093(7) -0.011(5) -0.015(6) -0.004(4) C4A 0.069(7) 0.045(5) 0.077(7) -0.007(5) -0.020(6) -0.002(5) C5A 0.060(6) 0.057(6) 0.100(7) -0.012(5) -0.011(6) -0.008(5) C6A 0.072(7) 0.070(7) 0.114(9) -0.005(6) -0.025(7) 0.001(5) C7A 0.077(7) 0.054(6) 0.119(9) -0.014(6) -0.012(8) -0.002(5) C8A 0.073(7) 0.062(6) 0.100(7) -0.017(5) -0.005(7) -0.014(5) C9A 0.051(6) 0.072(6) 0.092(8) -0.011(5) -0.007(6) 0.011(5) C10A 0.061(6) 0.052(6) 0.090(7) -0.014(5) -0.016(6) 0.012(5) C11A 0.063(6) 0.044(6) 0.113(7) -0.006(5) -0.025(5) -0.004(5) C12A 0.078(7) 0.054(6) 0.139(9) -0.006(6) -0.007(7) -0.035(6) C13A 0.074(7) 0.094(9) 0.136(9) -0.028(7) -0.029(7) 0.004(6) C14A 0.097(8) 0.070(7) 0.122(8) 0.005(6) -0.046(7) -0.001(6) C15A 0.072(6) 0.056(6) 0.118(8) -0.007(6) -0.009(6) -0.012(5) O2A 0.089(4) 0.060(4) 0.113(5) -0.031(3) -0.006(4) -0.004(3) N1A 0.098(6) 0.068(6) 0.113(6) -0.015(5) 0.013(5) -0.014(5) C16A 0.080(8) 0.049(7) 0.115(8) -0.021(6) -0.006(7) -0.011(6) C17A 0.081(8) 0.063(6) 0.138(10) -0.037(6) -0.010(7) -0.015(6) C18A 0.082(8) 0.123(10) 0.123(9) -0.045(8) -0.016(6) -0.010(8) C19A 0.087(8) 0.081(8) 0.107(8) -0.013(6) -0.021(7) 0.008(7) C20A 0.104(9) 0.056(6) 0.122(10) -0.020(6) 0.016(8) -0.002(6) O1B 0.154(6) 0.097(5) 0.083(5) -0.018(4) -0.003(4) 0.026(4) C1B 0.090(7) 0.052(7) 0.133(8) -0.018(6) -0.005(6) 0.009(6) C2B 0.072(6) 0.058(7) 0.136(8) -0.023(6) 0.002(6) 0.004(5) C3B 0.109(8) 0.040(6) 0.082(7) -0.013(5) -0.012(7) 0.030(6) C4B 0.074(7) 0.045(6) 0.088(8) -0.003(5) -0.008(7) 0.006(5) C5B 0.088(7) 0.062(6) 0.106(8) -0.025(5) -0.003(7) 0.008(5) C6B 0.089(8) 0.062(6) 0.106(8) -0.008(6) -0.028(7) -0.003(6) C7B 0.076(7) 0.056(6) 0.139(10) -0.015(6) -0.016(8) 0.011(5) C8B 0.090(7) 0.085(7) 0.098(8) -0.009(6) 0.010(7) -0.011(6) C9B 0.092(8) 0.060(6) 0.104(9) -0.011(6) 0.015(7) 0.002(6) C10B 0.110(8) 0.035(7) 0.112(8) 0.014(6) -0.011(7) 0.001(6) C11B 0.126(10) 0.086(9) 0.115(9) -0.013(8) -0.013(8) 0.014(8) C12B 0.131(11) 0.067(9) 0.158(12) 0.005(8) -0.014(9) 0.015(8) C13B 0.101(8) 0.042(7) 0.204(13) -0.038(8) -0.009(9) -0.015(6) C14B 0.099(8) 0.058(7) 0.190(12) -0.020(8) -0.016(8) -0.006(7) C15B 0.118(9) 0.040(6) 0.118(9) 0.008(6) -0.014(7) 0.007(7) O2B 0.111(5) 0.057(4) 0.114(5) -0.031(3) -0.003(4) -0.010(4) N1B 0.132(8) 0.068(6) 0.180(9) -0.031(6) -0.005(7) -0.038(6) C16B 0.112(10) 0.069(8) 0.106(8) -0.030(6) -0.023(8) -0.012(7) C17B 0.101(10) 0.075(8) 0.178(14) -0.036(8) 0.011(10) -0.011(8) C18B 0.139(13) 0.166(14) 0.167(13) -0.046(13) -0.026(10) -0.019(14) C19B 0.085(10) 0.169(15) 0.123(10) 0.035(11) -0.010(8) 0.030(10) C20B 0.155(13) 0.037(6) 0.197(15) -0.046(7) 0.059(13) -0.009(7) O1C 0.105(5) 0.065(4) 0.090(5) -0.017(3) -0.004(4) -0.003(3) C1C 0.084(7) 0.057(7) 0.110(7) -0.008(6) -0.018(6) 0.005(5) C2C 0.083(6) 0.041(6) 0.121(8) -0.014(5) -0.021(6) 0.008(5) C3C 0.084(7) 0.052(6) 0.095(8) -0.013(5) -0.002(7) 0.000(5) C4C 0.094(8) 0.033(5) 0.100(8) -0.011(5) -0.020(7) -0.009(5) C5C 0.064(6) 0.059(6) 0.147(9) -0.008(6) -0.025(7) 0.002(5) C6C 0.088(10) 0.053(7) 0.164(11) 0.007(7) -0.035(9) -0.006(6) C7C 0.058(7) 0.047(7) 0.206(14) -0.012(8) -0.004(10) -0.012(5) C8C 0.090(8) 0.068(7) 0.144(10) -0.040(7) 0.021(9) -0.011(6) C9C 0.107(9) 0.058(6) 0.106(9) -0.016(6) -0.022(7) -0.003(6) C10C 0.073(6) 0.036(6) 0.104(7) -0.022(5) -0.010(6) -0.009(5) C11C 0.095(7) 0.036(6) 0.160(9) -0.039(6) -0.022(7) -0.020(5) C12C 0.095(8) 0.052(6) 0.119(8) -0.013(6) 0.007(7) 0.011(6) C13C 0.103(9) 0.084(9) 0.131(9) -0.033(7) -0.007(7) -0.006(7) C14C 0.095(8) 0.100(9) 0.141(10) -0.021(8) -0.031(7) -0.011(7) C15C 0.098(8) 0.063(7) 0.115(8) -0.007(6) -0.039(7) -0.001(6) O2C 0.175(8) 0.133(7) 0.141(7) -0.038(5) 0.001(6) 0.058(6) N1C 0.151(9) 0.082(7) 0.173(10) -0.042(7) 0.008(7) 0.000(7) C16C 0.132(12) 0.092(10) 0.098(8) -0.017(7) 0.013(8) 0.025(9) C17C 0.145(13) 0.085(9) 0.180(14) -0.072(9) 0.005(12) -0.016(9) C18C 0.115(10) 0.153(13) 0.198(14) -0.083(12) -0.013(9) 0.029(12) C19C 0.171(15) 0.088(10) 0.111(9) -0.004(8) 0.001(10) 0.043(11) C20C 0.188(15) 0.063(8) 0.160(14) -0.023(8) 0.013(13) -0.014(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 O1A C3A 1.420(8) . ? O1A H1OA 0.8200 . ? C1A C2A 1.195(9) . ? C1A C1A 1.401(17) 2_656 ? C2A C3A 1.467(11) . ? C3A C10A 1.527(10) . ? C3A C4A 1.541(10) . ? C4A C5A 1.356(9) . ? C4A C9A 1.362(10) . ? C5A C6A 1.405(10) . ? C5A H5A 0.9300 . ? C6A C7A 1.373(10) . ? C6A H6A 0.9300 . ? C7A C8A 1.363(10) . ? C7A H7A 0.9300 . ? C8A C9A 1.387(10) . ? C8A H8A 0.9300 . ? C9A H9A 0.9300 . ? C10A C15A 1.375(10) . ? C10A C11A 1.411(10) . ? C11A C12A 1.357(10) . ? C11A H11A 0.9300 . ? C12A C13A 1.351(11) . ? C12A H12A 0.9300 . ? C13A C14A 1.361(11) . ? C13A H13A 0.9300 . ? C14A C15A 1.391(11) . ? C14A H14A 0.9300 . ? C15A H15A 0.9300 . ? O2A C16A 1.216(9) . ? N1A C16A 1.327(10) . ? N1A C20A 1.479(10) . ? N1A H1NA 0.8600 . ? C16A C17A 1.511(12) . ? C17A C18A 1.502(11) . ? C17A C20A 1.646(12) 2_756 ? C17A H17A 0.9800 . ? C18A C19A 1.293(12) . ? C18A H18A 0.9300 . ? C19A C20A 1.455(12) . ? C19A H19A 0.9300 . ? C20A C17A 1.646(12) 2_756 ? C20A H20A 0.9800 . ? O1B C3B 1.411(9) . ? O1B H1OB 0.8200 . ? C1B C2B 1.225(11) . ? C1B C1C 1.383(12) . ? C2B C3B 1.475(11) . ? C3B C10B 1.524(12) . ? C3B C4B 1.536(11) . ? C4B C9B 1.369(10) . ? C4B C5B 1.388(10) . ? C5B C6B 1.393(10) . ? C5B H5B 0.9300 . ? C6B C7B 1.363(11) . ? C6B H6B 0.9300 . ? C7B C8B 1.379(11) . ? C7B H7B 0.9300 . ? C8B C9B 1.385(10) . ? C8B H8B 0.9300 . ? C9B H9B 0.9300 . ? C10B C15B 1.348(11) . ? C10B C11B 1.395(12) . ? C11B C12B 1.415(13) . ? C11B H11B 0.9300 . ? C12B C13B 1.377(13) . ? C12B H12B 0.9300 . ? C13B C14B 1.358(13) . ? C13B H13B 0.9300 . ? C14B C15B 1.405(12) . ? C14B H14B 0.9300 . ? C15B H15B 0.9300 . ? O2B C16B 1.256(10) . ? N1B C16B 1.358(11) . ? N1B C20B 1.486(12) . ? N1B H1NB 0.8600 . ? C16B C17B 1.481(13) . ? C17B C18B 1.417(15) . ? C17B C20C 1.673(15) . ? C17B H17B 0.9800 . ? C18B C19B 1.308(16) . ? C18B H18B 0.9300 . ? C19B C20B 1.450(15) . ? C19B H19B 0.9300 . ? C20B C17C 1.674(16) . ? C20B H20B 0.9800 . ? O1C C3C 1.442(9) . ? O1C H1OC 0.8200 . ? C1C C2C 1.186(10) . ? C2C C3C 1.480(11) . ? C3C C10C 1.531(11) . ? C3C C4C 1.541(11) . ? C4C C5C 1.373(10) . ? C4C C9C 1.426(11) . ? C5C C6C 1.382(12) . ? C5C H5C 0.9300 . ? C6C C7C 1.377(12) . ? C6C H6C 0.9300 . ? C7C C8C 1.347(12) . ? C7C H7C 0.9300 . ? C8C C9C 1.401(11) . ? C8C H8C 0.9300 . ? C9C H9C 0.9300 . ? C10C C15C 1.352(10) . ? C10C C11C 1.367(10) . ? C11C C12C 1.394(11) . ? C11C H11C 0.9300 . ? C12C C13C 1.409(11) . ? C12C H12C 0.9300 . ? C13C C14C 1.379(12) . ? C13C H13C 0.9300 . ? C14C C15C 1.383(11) . ? C14C H14C 0.9300 . ? C15C H15C 0.9300 . ? O2C C16C 1.221(11) . ? N1C C16C 1.344(13) . ? N1C C20C 1.440(14) . ? N1C H1NC 0.8600 . ? C16C C17C 1.516(15) . ? C17C C18C 1.471(15) . ? C17C H17C 0.9800 . ? C18C C19C 1.254(15) . ? C18C H18C 0.9300 . ? C19C C20C 1.476(16) . ? C19C H19C 0.9300 . ? C20C H20C 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 C3A O1A H1OA 109.5 . . ? C2A C1A C1A 176.3(12) . 2_656 ? C1A C2A C3A 174.7(9) . . ? O1A C3A C2A 109.9(7) . . ? O1A C3A C10A 104.4(7) . . ? C2A C3A C10A 112.8(7) . . ? O1A C3A C4A 113.1(7) . . ? C2A C3A C4A 109.1(7) . . ? C10A C3A C4A 107.4(6) . . ? C5A C4A C9A 119.1(9) . . ? C5A C4A C3A 120.3(9) . . ? C9A C4A C3A 120.5(8) . . ? C4A C5A C6A 120.0(9) . . ? C4A C5A H5A 120.0 . . ? C6A C5A H5A 120.0 . . ? C7A C6A C5A 120.1(9) . . ? C7A C6A H6A 120.0 . . ? C5A C6A H6A 120.0 . . ? C8A C7A C6A 119.8(10) . . ? C8A C7A H7A 120.1 . . ? C6A C7A H7A 120.1 . . ? C7A C8A C9A 119.2(9) . . ? C7A C8A H8A 120.4 . . ? C9A C8A H8A 120.4 . . ? C4A C9A C8A 121.9(9) . . ? C4A C9A H9A 119.1 . . ? C8A C9A H9A 119.1 . . ? C15A C10A C11A 115.9(8) . . ? C15A C10A C3A 122.7(8) . . ? C11A C10A C3A 121.4(8) . . ? C12A C11A C10A 121.6(8) . . ? C12A C11A H11A 119.2 . . ? C10A C11A H11A 119.2 . . ? C13A C12A C11A 121.0(9) . . ? C13A C12A H12A 119.5 . . ? C11A C12A H12A 119.5 . . ? C12A C13A C14A 119.8(10) . . ? C12A C13A H13A 120.1 . . ? C14A C13A H13A 120.1 . . ? C13A C14A C15A 119.8(9) . . ? C13A C14A H14A 120.1 . . ? C15A C14A H14A 120.1 . . ? C10A C15A C14A 121.8(9) . . ? C10A C15A H15A 119.1 . . ? C14A C15A H15A 119.1 . . ? C16A N1A C20A 121.8(8) . . ? C16A N1A H1NA 119.1 . . ? C20A N1A H1NA 119.1 . . ? O2A C16A N1A 122.3(10) . . ? O2A C16A C17A 125.4(9) . . ? N1A C16A C17A 112.2(9) . . ? C18A C17A C16A 110.0(8) . . ? C18A C17A C20A 110.8(8) . 2_756 ? C16A C17A C20A 109.6(8) . 2_756 ? C18A C17A H17A 108.8 . . ? C16A C17A H17A 108.8 . . ? C20A C17A H17A 108.8 2_756 . ? C19A C18A C17A 118.0(10) . . ? C19A C18A H18A 121.0 . . ? C17A C18A H18A 121.0 . . ? C18A C19A C20A 118.0(9) . . ? C18A C19A H19A 121.0 . . ? C20A C19A H19A 121.0 . . ? C19A C20A N1A 108.0(8) . . ? C19A C20A C17A 111.6(8) . 2_756 ? N1A C20A C17A 110.3(8) . 2_756 ? C19A C20A H20A 108.9 . . ? N1A C20A H20A 108.9 . . ? C17A C20A H20A 108.9 2_756 . ? C3B O1B H1OB 109.5 . . ? C2B C1B C1C 176.6(10) . . ? C1B C2B C3B 170.7(10) . . ? O1B C3B C2B 108.8(7) . . ? O1B C3B C10B 114.5(9) . . ? C2B C3B C10B 110.5(8) . . ? O1B C3B C4B 106.8(8) . . ? C2B C3B C4B 107.8(7) . . ? C10B C3B C4B 108.1(7) . . ? C9B C4B C5B 118.7(9) . . ? C9B C4B C3B 121.6(9) . . ? C5B C4B C3B 119.5(9) . . ? C4B C5B C6B 120.4(9) . . ? C4B C5B H5B 119.8 . . ? C6B C5B H5B 119.8 . . ? C7B C6B C5B 120.5(9) . . ? C7B C6B H6B 119.7 . . ? C5B C6B H6B 119.7 . . ? C6B C7B C8B 119.0(10) . . ? C6B C7B H7B 120.5 . . ? C8B C7B H7B 120.5 . . ? C7B C8B C9B 120.8(9) . . ? C7B C8B H8B 119.6 . . ? C9B C8B H8B 119.6 . . ? C4B C9B C8B 120.6(9) . . ? C4B C9B H9B 119.7 . . ? C8B C9B H9B 119.7 . . ? C15B C10B C11B 120.9(11) . . ? C15B C10B C3B 123.4(10) . . ? C11B C10B C3B 115.7(12) . . ? C10B C11B C12B 119.2(11) . . ? C10B C11B H11B 120.4 . . ? C12B C11B H11B 120.4 . . ? C13B C12B C11B 119.1(11) . . ? C13B C12B H12B 120.5 . . ? C11B C12B H12B 120.5 . . ? C14B C13B C12B 120.4(11) . . ? C14B C13B H13B 119.8 . . ? C12B C13B H13B 119.8 . . ? C13B C14B C15B 121.1(11) . . ? C13B C14B H14B 119.5 . . ? C15B C14B H14B 119.5 . . ? C10B C15B C14B 119.3(10) . . ? C10B C15B H15B 120.3 . . ? C14B C15B H15B 120.3 . . ? C16B N1B C20B 118.5(9) . . ? C16B N1B H1NB 120.7 . . ? C20B N1B H1NB 120.7 . . ? O2B C16B N1B 121.4(11) . . ? O2B C16B C17B 124.3(10) . . ? N1B C16B C17B 114.2(10) . . ? C18B C17B C16B 112.8(11) . . ? C18B C17B C20C 105.6(11) . . ? C16B C17B C20C 110.1(11) . . ? C18B C17B H17B 109.4 . . ? C16B C17B H17B 109.4 . . ? C20C C17B H17B 109.4 . . ? C19B C18B C17B 120.9(15) . . ? C19B C18B H18B 119.6 . . ? C17B C18B H18B 119.6 . . ? C18B C19B C20B 115.9(12) . . ? C18B C19B H19B 122.1 . . ? C20B C19B H19B 122.1 . . ? C19B C20B N1B 110.1(10) . . ? C19B C20B C17C 113.1(11) . . ? N1B C20B C17C 106.2(12) . . ? C19B C20B H20B 109.1 . . ? N1B C20B H20B 109.1 . . ? C17C C20B H20B 109.1 . . ? C3C O1C H1OC 109.5 . . ? C2C C1C C1B 177.0(10) . . ? C1C C2C C3C 176.9(10) . . ? O1C C3C C2C 109.6(7) . . ? O1C C3C C10C 108.4(7) . . ? C2C C3C C10C 112.8(8) . . ? O1C C3C C4C 108.6(7) . . ? C2C C3C C4C 107.3(7) . . ? C10C C3C C4C 110.1(7) . . ? C5C C4C C9C 116.6(9) . . ? C5C C4C C3C 122.4(10) . . ? C9C C4C C3C 120.9(9) . . ? C4C C5C C6C 121.9(10) . . ? C4C C5C H5C 119.0 . . ? C6C C5C H5C 119.0 . . ? C7C C6C C5C 119.8(11) . . ? C7C C6C H6C 120.1 . . ? C5C C6C H6C 120.1 . . ? C8C C7C C6C 121.5(12) . . ? C8C C7C H7C 119.3 . . ? C6C C7C H7C 119.3 . . ? C7C C8C C9C 119.0(11) . . ? C7C C8C H8C 120.5 . . ? C9C C8C H8C 120.5 . . ? C8C C9C C4C 121.2(9) . . ? C8C C9C H9C 119.4 . . ? C4C C9C H9C 119.4 . . ? C15C C10C C11C 122.7(9) . . ? C15C C10C C3C 122.1(9) . . ? C11C C10C C3C 115.2(9) . . ? C10C C11C C12C 117.6(9) . . ? C10C C11C H11C 121.2 . . ? C12C C11C H11C 121.2 . . ? C11C C12C C13C 122.2(9) . . ? C11C C12C H12C 118.9 . . ? C13C C12C H12C 118.9 . . ? C14C C13C C12C 116.2(10) . . ? C14C C13C H13C 121.9 . . ? C12C C13C H13C 121.9 . . ? C13C C14C C15C 122.4(10) . . ? C13C C14C H14C 118.8 . . ? C15C C14C H14C 118.8 . . ? C10C C15C C14C 119.0(9) . . ? C10C C15C H15C 120.5 . . ? C14C C15C H15C 120.5 . . ? C16C N1C C20C 120.1(11) . . ? C16C N1C H1NC 119.9 . . ? C20C N1C H1NC 119.9 . . ? O2C C16C N1C 124.9(15) . . ? O2C C16C C17C 121.6(14) . . ? N1C C16C C17C 113.5(10) . . ? C18C C17C C16C 109.6(12) . . ? C18C C17C C20B 110.4(12) . . ? C16C C17C C20B 107.9(10) . . ? C18C C17C H17C 109.6 . . ? C16C C17C H17C 109.6 . . ? C20B C17C H17C 109.6 . . ? C19C C18C C17C 120.4(14) . . ? C19C C18C H18C 119.8 . . ? C17C C18C H18C 119.8 . . ? C18C C19C C20C 117.1(13) . . ? C18C C19C H19C 121.4 . . ? C20C C19C H19C 121.4 . . ? N1C C20C C19C 109.1(11) . . ? N1C C20C C17B 111.2(12) . . ? C19C C20C C17B 110.3(12) . . ? N1C C20C H20C 108.8 . . ? C19C C20C H20C 108.8 . . ? C17B C20C H20C 108.8 . . ? 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 C1A C2A C3A -60(24) 2_656 . . . ? C1A C2A C3A O1A -17(10) . . . . ? C1A C2A C3A C10A -133(10) . . . . ? C1A C2A C3A C4A 107(10) . . . . ? O1A C3A C4A C5A -6.8(10) . . . . ? C2A C3A C4A C5A -129.5(8) . . . . ? C10A C3A C4A C5A 107.9(9) . . . . ? O1A C3A C4A C9A 176.8(7) . . . . ? C2A C3A C4A C9A 54.1(10) . . . . ? C10A C3A C4A C9A -68.5(9) . . . . ? C9A C4A C5A C6A -1.1(12) . . . . ? C3A C4A C5A C6A -177.6(7) . . . . ? C4A C5A C6A C7A 1.4(12) . . . . ? C5A C6A C7A C8A -1.3(13) . . . . ? C6A C7A C8A C9A 0.9(12) . . . . ? C5A C4A C9A C8A 0.8(12) . . . . ? C3A C4A C9A C8A 177.3(7) . . . . ? C7A C8A C9A C4A -0.7(12) . . . . ? O1A C3A C10A C15A -129.2(8) . . . . ? C2A C3A C10A C15A -9.9(11) . . . . ? C4A C3A C10A C15A 110.4(8) . . . . ? O1A C3A C10A C11A 51.5(9) . . . . ? C2A C3A C10A C11A 170.9(7) . . . . ? C4A C3A C10A C11A -68.9(10) . . . . ? C15A C10A C11A C12A 3.8(12) . . . . ? C3A C10A C11A C12A -176.9(8) . . . . ? C10A C11A C12A C13A -2.4(14) . . . . ? C11A C12A C13A C14A -1.0(15) . . . . ? C12A C13A C14A C15A 2.8(15) . . . . ? C11A C10A C15A C14A -2.0(12) . . . . ? C3A C10A C15A C14A 178.7(8) . . . . ? C13A C14A C15A C10A -1.2(14) . . . . ? C20A N1A C16A O2A -179.1(9) . . . . ? C20A N1A C16A C17A -2.1(13) . . . . ? O2A C16A C17A C18A 135.8(9) . . . . ? N1A C16A C17A C18A -41.2(11) . . . . ? O2A C16A C17A C20A -102.2(10) . . . 2_756 ? N1A C16A C17A C20A 80.9(9) . . . 2_756 ? C16A C17A C18A C19A 44.0(13) . . . . ? C20A C17A C18A C19A -77.4(11) 2_756 . . . ? C17A C18A C19A C20A 0.0(15) . . . . ? C18A C19A C20A N1A -42.6(13) . . . . ? C18A C19A C20A C17A 78.8(11) . . . 2_756 ? C16A N1A C20A C19A 44.7(12) . . . . ? C16A N1A C20A C17A -77.5(11) . . . 2_756 ? C1C C1B C2B C3B 108(18) . . . . ? C1B C2B C3B O1B -36(6) . . . . ? C1B C2B C3B C10B -163(6) . . . . ? C1B C2B C3B C4B 79(6) . . . . ? O1B C3B C4B C9B 163.4(8) . . . . ? C2B C3B C4B C9B 46.6(12) . . . . ? C10B C3B C4B C9B -72.8(11) . . . . ? O1B C3B C4B C5B -22.7(11) . . . . ? C2B C3B C4B C5B -139.5(8) . . . . ? C10B C3B C4B C5B 101.0(10) . . . . ? C9B C4B C5B C6B -2.5(12) . . . . ? C3B C4B C5B C6B -176.6(8) . . . . ? C4B C5B C6B C7B 2.8(13) . . . . ? C5B C6B C7B C8B -1.2(14) . . . . ? C6B C7B C8B C9B -0.7(14) . . . . ? C5B C4B C9B C8B 0.7(13) . . . . ? C3B C4B C9B C8B 174.7(8) . . . . ? C7B C8B C9B C4B 0.9(13) . . . . ? O1B C3B C10B C15B -138.8(9) . . . . ? C2B C3B C10B C15B -15.5(12) . . . . ? C4B C3B C10B C15B 102.2(10) . . . . ? O1B C3B C10B C11B 39.1(11) . . . . ? C2B C3B C10B C11B 162.4(8) . . . . ? C4B C3B C10B C11B -79.9(10) . . . . ? C15B C10B C11B C12B -3.2(14) . . . . ? C3B C10B C11B C12B 178.8(9) . . . . ? C10B C11B C12B C13B 2.4(15) . . . . ? C11B C12B C13B C14B -0.6(16) . . . . ? C12B C13B C14B C15B -0.5(16) . . . . ? C11B C10B C15B C14B 2.1(14) . . . . ? C3B C10B C15B C14B 180.0(8) . . . . ? C13B C14B C15B C10B -0.3(15) . . . . ? C20B N1B C16B O2B 176.1(11) . . . . ? C20B N1B C16B C17B -1.9(16) . . . . ? O2B C16B C17B C18B -138.5(11) . . . . ? N1B C16B C17B C18B 39.5(15) . . . . ? O2B C16B C17B C20C 103.8(11) . . . . ? N1B C16B C17B C20C -78.3(11) . . . . ? C16B C17B C18B C19B -35.2(19) . . . . ? C20C C17B C18B C19B 85.1(17) . . . . ? C17B C18B C19B C20B -9(2) . . . . ? C18B C19B C20B N1B 45.7(17) . . . . ? C18B C19B C20B C17C -73.0(17) . . . . ? C16B N1B C20B C19B -39.9(16) . . . . ? C16B N1B C20B C17C 82.9(12) . . . . ? C2B C1B C1C C2C -32(33) . . . . ? C1B C1C C2C C3C 145(18) . . . . ? C1C C2C C3C O1C 0(18) . . . . ? C1C C2C C3C C10C 121(18) . . . . ? C1C C2C C3C C4C -118(18) . . . . ? O1C C3C C4C C5C 12.3(10) . . . . ? C2C C3C C4C C5C 130.6(8) . . . . ? C10C C3C C4C C5C -106.3(9) . . . . ? O1C C3C C4C C9C -171.5(7) . . . . ? C2C C3C C4C C9C -53.2(10) . . . . ? C10C C3C C4C C9C 69.9(10) . . . . ? C9C C4C C5C C6C 0.7(12) . . . . ? C3C C4C C5C C6C 177.1(8) . . . . ? C4C C5C C6C C7C -0.1(14) . . . . ? C5C C6C C7C C8C -0.2(15) . . . . ? C6C C7C C8C C9C -0.2(14) . . . . ? C7C C8C C9C C4C 0.8(13) . . . . ? C5C C4C C9C C8C -1.0(12) . . . . ? C3C C4C C9C C8C -177.5(7) . . . . ? O1C C3C C10C C15C 128.0(9) . . . . ? C2C C3C C10C C15C 6.4(12) . . . . ? C4C C3C C10C C15C -113.4(9) . . . . ? O1C C3C C10C C11C -51.0(9) . . . . ? C2C C3C C10C C11C -172.5(7) . . . . ? C4C C3C C10C C11C 67.7(10) . . . . ? C15C C10C C11C C12C -0.1(13) . . . . ? C3C C10C C11C C12C 178.8(8) . . . . ? C10C C11C C12C C13C 0.8(13) . . . . ? C11C C12C C13C C14C -0.7(14) . . . . ? C12C C13C C14C C15C -0.1(15) . . . . ? C11C C10C C15C C14C -0.7(14) . . . . ? C3C C10C C15C C14C -179.6(8) . . . . ? C13C C14C C15C C10C 0.8(15) . . . . ? C20C N1C C16C O2C -179.7(12) . . . . ? C20C N1C C16C C17C 0.7(17) . . . . ? O2C C16C C17C C18C 139.7(11) . . . . ? N1C C16C C17C C18C -40.6(15) . . . . ? O2C C16C C17C C20B -100.0(12) . . . . ? N1C C16C C17C C20B 79.7(11) . . . . ? C19B C20B C17C C18C 115.4(16) . . . . ? N1B C20B C17C C18C -5.5(15) . . . . ? C19B C20B C17C C16C -4.4(15) . . . . ? N1B C20B C17C C16C -125.3(11) . . . . ? C16C C17C C18C C19C 38.8(19) . . . . ? C20B C17C C18C C19C -80.0(18) . . . . ? C17C C18C C19C C20C 5(2) . . . . ? C16C N1C C20C C19C 42.1(17) . . . . ? C16C N1C C20C C17B -79.7(14) . . . . ? C18C C19C C20C N1C -45.8(18) . . . . ? C18C C19C C20C C17B 76.6(16) . . . . ? C18B C17B C20C N1C -0.5(15) . . . . ? C16B C17B C20C N1C 121.6(12) . . . . ? C18B C17B C20C C19C -121.6(14) . . . . ? C16B C17B C20C C19C 0.5(15) . . . . ? _diffrn_measured_fraction_theta_max 0.852 _diffrn_reflns_theta_full 22.25 _diffrn_measured_fraction_theta_full 0.852 _refine_diff_density_max 0.372 _refine_diff_density_min -0.294 _refine_diff_density_rms 0.062 # Attachment '1-b.cif' data_pyr102r0 _database_code_depnum_ccdc_archive 'CCDC 603861' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,1,6,6-tetraphenyl-2,4- hexadiyne-1,6-diol bis(2-(1H)-pyridone) clathrate ; _chemical_name_common ;1,1,6,6-tetraphenyl-2,4- hexadiyne-1,6-diol bis(2-(1H)- pyridone) clathrate ; _chemical_melting_point ? _chemical_formula_moiety '(C30 H22 O2), 2(C5 H5 N O)' _chemical_formula_sum 'C20 H16 N O2' _chemical_formula_weight 302.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7919(2) _cell_length_b 8.0674(3) _cell_length_c 13.4552(6) _cell_angle_alpha 85.0897(14) _cell_angle_beta 75.6634(13) _cell_angle_gamma 81.160(2) _cell_volume 808.72(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2756 _cell_measurement_theta_min 1.018 _cell_measurement_theta_max 27.485 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.242 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 318 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details none _exptl_special_details ; ? ; _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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 4896 _diffrn_reflns_av_R_equivalents 0.0219 _diffrn_reflns_av_sigmaI/netI 0.0505 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 25.05 _reflns_number_total 2854 _reflns_number_gt 1881 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_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^)+(0.0611P)^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 0.056(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2854 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0594 _refine_ls_R_factor_gt 0.0369 _refine_ls_wR_factor_ref 0.1002 _refine_ls_wR_factor_gt 0.0947 _refine_ls_goodness_of_fit_ref 0.912 _refine_ls_restrained_S_all 0.912 _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 0.85458(12) 0.08066(13) 0.23549(7) 0.0502(3) Uani 1 1 d . . . H1O1 H 0.926(2) 0.019(2) 0.2724(14) 0.092(6) Uiso 1 1 d . . . C1 C 0.53950(17) -0.00185(17) 0.44770(10) 0.0503(4) Uani 1 1 d . . . C2 C 0.60691(17) -0.00499(17) 0.35827(10) 0.0482(4) Uani 1 1 d . . . C3 C 0.70276(15) -0.00475(16) 0.24839(9) 0.0419(3) Uani 1 1 d . . . C4 C 0.76036(16) -0.18622(17) 0.21444(9) 0.0421(3) Uani 1 1 d . . . C5 C 0.92943(17) -0.23453(19) 0.15398(10) 0.0536(4) Uani 1 1 d . . . H5 H 1.0105 -0.1574 0.1349 0.064 Uiso 1 1 calc R . . C6 C 0.9783(2) -0.3966(2) 0.12188(11) 0.0637(4) Uani 1 1 d . . . H6 H 1.0927 -0.4282 0.0818 0.076 Uiso 1 1 calc R . . C7 C 0.8606(2) -0.5110(2) 0.14833(11) 0.0652(4) Uani 1 1 d . . . H7 H 0.8949 -0.6203 0.1268 0.078 Uiso 1 1 calc R . . C8 C 0.6914(2) -0.4642(2) 0.20679(12) 0.0663(4) Uani 1 1 d . . . H8 H 0.6103 -0.5415 0.2241 0.080 Uiso 1 1 calc R . . C9 C 0.64113(19) -0.30233(18) 0.24009(11) 0.0559(4) Uani 1 1 d . . . H9 H 0.5265 -0.2714 0.2800 0.067 Uiso 1 1 calc R . . C10 C 0.58535(16) 0.08838(16) 0.17995(9) 0.0426(3) Uani 1 1 d . . . C11 C 0.66410(18) 0.14024(19) 0.08084(10) 0.0549(4) Uani 1 1 d . . . H11 H 0.7880 0.1232 0.0579 0.066 Uiso 1 1 calc R . . C12 C 0.5613(2) 0.2170(2) 0.01557(11) 0.0665(4) Uani 1 1 d . . . H12 H 0.6161 0.2519 -0.0508 0.080 Uiso 1 1 calc R . . C13 C 0.3780(2) 0.2422(2) 0.04820(13) 0.0720(5) Uani 1 1 d . . . H13 H 0.3085 0.2941 0.0042 0.086 Uiso 1 1 calc R . . C14 C 0.2989(2) 0.1905(2) 0.14563(14) 0.0774(5) Uani 1 1 d . . . H14 H 0.1749 0.2066 0.1679 0.093 Uiso 1 1 calc R . . C15 C 0.40148(18) 0.1142(2) 0.21188(11) 0.0607(4) Uani 1 1 d . . . H15 H 0.3459 0.0802 0.2783 0.073 Uiso 1 1 calc R . . O2 O 1.03942(15) -0.06948(17) 0.37506(8) 0.0816(4) Uani 1 1 d . . . N1 N 1.11918(18) -0.2147(2) 0.51076(11) 0.0717(4) Uani 1 1 d . . . C16 C 1.10552(19) -0.2069(2) 0.41211(13) 0.0658(4) Uani 1 1 d . . . C17 C 1.1692(2) -0.3560(3) 0.35910(14) 0.0810(5) Uani 1 1 d . . . H17 H 1.1616 -0.3586 0.2914 0.097 Uiso 1 1 calc R . . C18 C 1.2416(2) -0.4958(3) 0.40575(17) 0.0870(6) Uani 1 1 d . . . H18 H 1.2841 -0.5925 0.3692 0.104 Uiso 1 1 calc R . . C19 C 1.2532(2) -0.4967(3) 0.50697(17) 0.0903(6) Uani 1 1 d . . . H19 H 1.3021 -0.5926 0.5391 0.108 Uiso 1 1 calc R . . C20 C 1.1915(3) -0.3544(3) 0.55719(15) 0.0884(6) Uani 1 1 d . . . H20 H 1.1985 -0.3518 0.6250 0.106 Uiso 1 1 calc R . . H1N H 1.060(2) -0.114(3) 0.5629(14) 0.105(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0533(6) 0.0521(7) 0.0481(6) 0.0003(5) -0.0151(4) -0.0128(4) C1 0.0564(8) 0.0522(10) 0.0396(7) -0.0060(7) -0.0073(6) -0.0037(7) C2 0.0559(8) 0.0459(9) 0.0403(8) -0.0048(6) -0.0086(6) -0.0030(6) C3 0.0453(7) 0.0455(8) 0.0330(7) -0.0025(6) -0.0051(5) -0.0072(6) C4 0.0503(7) 0.0439(8) 0.0315(7) -0.0004(6) -0.0115(5) -0.0021(6) C5 0.0525(8) 0.0573(10) 0.0482(8) -0.0103(7) -0.0071(6) -0.0027(7) C6 0.0633(9) 0.0655(12) 0.0583(10) -0.0182(8) -0.0137(7) 0.0103(8) C7 0.0932(12) 0.0461(10) 0.0562(9) -0.0109(7) -0.0265(8) 0.0095(9) C8 0.0899(11) 0.0457(10) 0.0644(10) -0.0003(8) -0.0172(8) -0.0164(8) C9 0.0606(8) 0.0494(10) 0.0526(9) -0.0019(7) -0.0039(6) -0.0078(7) C10 0.0498(7) 0.0380(8) 0.0388(7) -0.0051(6) -0.0093(5) -0.0029(6) C11 0.0559(8) 0.0642(11) 0.0424(8) 0.0025(7) -0.0109(6) -0.0053(7) C12 0.0805(11) 0.0713(12) 0.0461(9) 0.0080(8) -0.0192(7) -0.0053(8) C13 0.0769(11) 0.0712(12) 0.0701(11) 0.0070(9) -0.0344(9) 0.0056(9) C14 0.0545(9) 0.0897(14) 0.0816(12) 0.0098(10) -0.0192(8) 0.0070(8) C15 0.0528(8) 0.0661(11) 0.0550(9) 0.0062(8) -0.0065(7) 0.0018(7) O2 0.0876(8) 0.0952(10) 0.0683(8) 0.0040(7) -0.0376(6) -0.0050(7) N1 0.0776(9) 0.0791(11) 0.0648(9) 0.0062(8) -0.0331(7) -0.0096(8) C16 0.0555(9) 0.0818(13) 0.0654(11) 0.0050(9) -0.0238(8) -0.0156(8) C17 0.0763(11) 0.0988(16) 0.0730(12) -0.0133(11) -0.0240(9) -0.0124(10) C18 0.0758(11) 0.0804(15) 0.1040(16) -0.0116(12) -0.0176(10) -0.0101(10) C19 0.0898(13) 0.0825(16) 0.0999(16) 0.0127(12) -0.0340(11) -0.0071(11) C20 0.1006(13) 0.0896(16) 0.0802(13) 0.0133(12) -0.0402(11) -0.0085(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 C3 1.4257(15) . ? O1 H1O1 0.904(18) . ? C1 C2 1.1886(16) . ? C1 C1 1.390(2) 2_656 ? C2 C3 1.4821(16) . ? C3 C10 1.5287(17) . ? C3 C4 1.5377(18) . ? C4 C9 1.3831(18) . ? C4 C5 1.3838(17) . ? C5 C6 1.380(2) . ? C5 H5 0.9300 . ? C6 C7 1.365(2) . ? C6 H6 0.9300 . ? C7 C8 1.373(2) . ? C7 H7 0.9300 . ? C8 C9 1.384(2) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C15 1.3782(18) . ? C10 C11 1.3813(17) . ? C11 C12 1.378(2) . ? C11 H11 0.9300 . ? C12 C13 1.375(2) . ? C12 H12 0.9300 . ? C13 C14 1.363(2) . ? C13 H13 0.9300 . ? C14 C15 1.386(2) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? O2 C16 1.265(2) . ? N1 C16 1.3531(19) . ? N1 C20 1.355(2) . ? N1 H1N 1.09(2) . ? C16 C17 1.411(3) . ? C17 C18 1.357(3) . ? C17 H17 0.9300 . ? C18 C19 1.386(3) . ? C18 H18 0.9300 . ? C19 C20 1.344(3) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 O1 H1O1 106.1(11) . . ? C2 C1 C1 179.9(2) . 2_656 ? C1 C2 C3 175.74(14) . . ? O1 C3 C2 108.44(10) . . ? O1 C3 C10 107.66(10) . . ? C2 C3 C10 111.63(10) . . ? O1 C3 C4 110.71(10) . . ? C2 C3 C4 109.91(10) . . ? C10 C3 C4 108.48(10) . . ? C9 C4 C5 118.74(13) . . ? C9 C4 C3 120.45(11) . . ? C5 C4 C3 120.75(12) . . ? C6 C5 C4 120.30(14) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C7 C6 C5 120.65(13) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C6 C7 C8 119.75(14) . . ? C6 C7 H7 120.1 . . ? C8 C7 H7 120.1 . . ? C7 C8 C9 120.14(14) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C4 C9 C8 120.41(13) . . ? C4 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C15 C10 C11 118.47(12) . . ? C15 C10 C3 122.03(11) . . ? C11 C10 C3 119.39(11) . . ? C12 C11 C10 120.78(13) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C13 C12 C11 120.29(14) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C14 C13 C12 119.38(14) . . ? C14 C13 H13 120.3 . . ? C12 C13 H13 120.3 . . ? C13 C14 C15 120.65(14) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C10 C15 C14 120.43(13) . . ? C10 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C16 N1 C20 123.29(18) . . ? C16 N1 H1N 123.1(10) . . ? C20 N1 H1N 113.3(9) . . ? O2 C16 N1 118.52(17) . . ? O2 C16 C17 125.67(16) . . ? N1 C16 C17 115.81(17) . . ? C18 C17 C16 120.80(17) . . ? C18 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? C17 C18 C19 121.0(2) . . ? C17 C18 H18 119.5 . . ? C19 C18 H18 119.5 . . ? C20 C19 C18 117.88(19) . . ? C20 C19 H19 121.1 . . ? C18 C19 H19 121.1 . . ? C19 C20 N1 121.19(19) . . ? C19 C20 H20 119.4 . . ? N1 C20 H20 119.4 . . ? 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 C1 C1 C2 C3 155(100) 2_656 . . . ? C1 C2 C3 O1 -12.7(19) . . . . ? C1 C2 C3 C10 -131.1(19) . . . . ? C1 C2 C3 C4 108.5(19) . . . . ? O1 C3 C4 C9 166.22(11) . . . . ? C2 C3 C4 C9 46.44(15) . . . . ? C10 C3 C4 C9 -75.86(14) . . . . ? O1 C3 C4 C5 -16.66(16) . . . . ? C2 C3 C4 C5 -136.43(12) . . . . ? C10 C3 C4 C5 101.27(13) . . . . ? C9 C4 C5 C6 -1.3(2) . . . . ? C3 C4 C5 C6 -178.44(12) . . . . ? C4 C5 C6 C7 0.6(2) . . . . ? C5 C6 C7 C8 0.5(2) . . . . ? C6 C7 C8 C9 -1.0(2) . . . . ? C5 C4 C9 C8 0.8(2) . . . . ? C3 C4 C9 C8 177.99(12) . . . . ? C7 C8 C9 C4 0.3(2) . . . . ? O1 C3 C10 C15 -139.89(13) . . . . ? C2 C3 C10 C15 -20.99(18) . . . . ? C4 C3 C10 C15 100.26(14) . . . . ? O1 C3 C10 C11 43.91(16) . . . . ? C2 C3 C10 C11 162.81(12) . . . . ? C4 C3 C10 C11 -75.94(15) . . . . ? C15 C10 C11 C12 0.4(2) . . . . ? C3 C10 C11 C12 176.74(14) . . . . ? C10 C11 C12 C13 -0.4(2) . . . . ? C11 C12 C13 C14 -0.1(3) . . . . ? C12 C13 C14 C15 0.5(3) . . . . ? C11 C10 C15 C14 0.0(2) . . . . ? C3 C10 C15 C14 -176.24(15) . . . . ? C13 C14 C15 C10 -0.4(3) . . . . ? C20 N1 C16 O2 -178.50(15) . . . . ? C20 N1 C16 C17 1.0(2) . . . . ? O2 C16 C17 C18 178.47(15) . . . . ? N1 C16 C17 C18 -1.0(2) . . . . ? C16 C17 C18 C19 0.7(3) . . . . ? C17 C18 C19 C20 -0.4(3) . . . . ? C18 C19 C20 N1 0.4(3) . . . . ? C16 N1 C20 C19 -0.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.136 _refine_diff_density_min -0.129 _refine_diff_density_rms 0.026