Supplementary information (ESI) for CrystEngComm This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _publ_section_title ;Controlled photochemical reaction of 4-oxo(phenylacetyl)morpholine and 1-(phenylglyoxylyl)piperidine in solid supramolecular systems ; _publ_contact_author_name 'Prof. Menahem Kaftory' _publ_contact_author_email KAFTORY@TX.TECHNION.AC.IL loop_ _publ_author_name 'Menahem Kaftory' 'J. Howard' 'Tali Lavy' 'Yana Sheynin' 'Hazel A. Sparkes' # Attachment 'IVa.cif' data_IVa _database_code_depnum_ccdc_archive 'CCDC 604708' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,4-hexadiyne-1,6-diol-1,6-bis(2-chlorophenyl)-1,6-diphenyl, 4-oxo(phenylacetyl)morpholine clathrate ; _chemical_name_common ; 2,4-hexadiyne-1,6-diol-1,6-bis(2-chlorophenyl)-1,6-diphenyl, 4-oxo(phenylacetyl)morpholine clathrate ; _chemical_melting_point ? _chemical_formula_moiety 'C30 H20 Cl2 O2, C12 H13 N O3' _chemical_formula_sum 'C42 H33 Cl2 N O5' _chemical_formula_weight 702.59 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.2078(2) _cell_length_b 24.8368(7) _cell_length_c 9.4738(3) _cell_angle_alpha 90.00 _cell_angle_beta 111.8526(10) _cell_angle_gamma 90.00 _cell_volume 1792.51(9) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3583 _cell_measurement_theta_min 1.018 _cell_measurement_theta_max 25.08 _chemical_absolute_configuration ad _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.302 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 732 _exptl_absorpt_coefficient_mu 0.228 _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 12082 _diffrn_reflns_av_R_equivalents 0.0856 _diffrn_reflns_av_sigmaI/netI 0.1478 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 27.35 _reflns_number_total 7122 _reflns_number_gt 3098 _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^)+(0.0663P)^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 0.027(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.92(8) _refine_ls_number_reflns 7122 _refine_ls_number_parameters 493 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.1424 _refine_ls_R_factor_gt 0.0584 _refine_ls_wR_factor_ref 0.1565 _refine_ls_wR_factor_gt 0.1317 _refine_ls_goodness_of_fit_ref 0.819 _refine_ls_restrained_S_all 0.818 _refine_ls_shift/su_max 0.028 _refine_ls_shift/su_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1A Cl 0.64946(17) 0.26390(6) 0.93636(16) 0.0821(4) Uani 1 1 d . . . O1A O 0.1092(4) 0.25323(13) 0.9651(3) 0.0623(8) Uani 1 1 d . . . H1A H 0.0971 0.2760 1.0230 0.093 Uiso 1 1 calc R . . C1A C 0.2996(6) 0.3678(2) 0.9011(5) 0.0579(12) Uani 1 1 d . . . C2A C 0.2890(6) 0.32011(19) 0.9179(5) 0.0535(11) Uani 1 1 d . . . C3A C 0.2706(5) 0.26218(17) 0.9449(5) 0.0502(10) Uani 1 1 d . . . C4A C 0.4319(6) 0.24671(16) 1.0910(5) 0.0546(11) Uani 1 1 d . . . C5A C 0.4050(7) 0.23335(18) 1.2233(6) 0.0648(13) Uani 1 1 d . . . H5A H 0.2919 0.2320 1.2235 0.078 Uiso 1 1 calc R . . C6A C 0.5491(8) 0.2220(2) 1.3558(6) 0.0735(14) Uani 1 1 d . . . H6A H 0.5312 0.2128 1.4441 0.088 Uiso 1 1 calc R . . C7A C 0.7140(8) 0.2240(2) 1.3575(7) 0.0774(15) Uani 1 1 d . . . H7A H 0.8081 0.2172 1.4478 0.093 Uiso 1 1 calc R . . C8A C 0.7452(7) 0.2358(2) 1.2310(7) 0.0739(15) Uani 1 1 d . . . H8A H 0.8591 0.2357 1.2323 0.089 Uiso 1 1 calc R . . C9A C 0.5996(7) 0.24832(17) 1.0949(5) 0.0598(12) Uani 1 1 d . . . C10A C 0.2568(6) 0.22677(19) 0.8083(5) 0.0578(12) Uani 1 1 d . . . C11A C 0.2092(6) 0.2492(2) 0.6646(6) 0.0730(14) Uani 1 1 d . . . H11A H 0.1877 0.2859 0.6489 0.088 Uiso 1 1 calc R . . C12A C 0.1948(7) 0.2145(4) 0.5438(7) 0.0969(19) Uani 1 1 d . . . H12A H 0.1662 0.2288 0.4468 0.116 Uiso 1 1 calc R . . C13A C 0.2209(9) 0.1614(4) 0.5635(9) 0.108(2) Uani 1 1 d . . . H13A H 0.2049 0.1395 0.4798 0.130 Uiso 1 1 calc R . . C14A C 0.2720(10) 0.1385(3) 0.7087(10) 0.115(2) Uani 1 1 d . . . H14A H 0.2953 0.1018 0.7240 0.139 Uiso 1 1 calc R . . C15A C 0.2865(8) 0.1726(2) 0.8290(7) 0.0851(17) Uani 1 1 d . . . H15A H 0.3171 0.1583 0.9262 0.102 Uiso 1 1 calc R . . Cl1B Cl -0.04317(19) 0.49436(6) 0.62132(16) 0.0915(5) Uani 1 1 d . . . O1B O 0.4935(5) 0.54886(14) 0.9441(4) 0.0823(11) Uani 1 1 d . . . H1B H 0.602(9) 0.533(3) 0.928(7) 0.123 Uiso 1 1 d . . . C1B C 0.3145(6) 0.4222(2) 0.8815(5) 0.0615(13) Uani 1 1 d . . . C2B C 0.3258(6) 0.4695(2) 0.8615(6) 0.0628(13) Uani 1 1 d . . . C3B C 0.3360(6) 0.52733(18) 0.8298(6) 0.0636(13) Uani 1 1 d . . . C4B C 0.1819(7) 0.55701(18) 0.8452(5) 0.0600(12) Uani 1 1 d . . . C5B C 0.2102(9) 0.5999(2) 0.9497(6) 0.0775(16) Uani 1 1 d . . . H5B H 0.3247 0.6093 1.0104 0.093 Uiso 1 1 calc R . . C6B C 0.0770(11) 0.6275(2) 0.9639(7) 0.0871(18) Uani 1 1 d . . . H6B H 0.1003 0.6561 1.0317 0.105 Uiso 1 1 calc R . . C7B C -0.0946(12) 0.6138(3) 0.8787(9) 0.105(2) Uani 1 1 d . . . H7B H -0.1871 0.6321 0.8913 0.126 Uiso 1 1 calc R . . C8B C -0.1272(8) 0.5717(2) 0.7728(7) 0.0825(16) Uani 1 1 d . . . H8B H -0.2417 0.5621 0.7132 0.099 Uiso 1 1 calc R . . C9B C 0.0087(7) 0.5457(2) 0.7588(6) 0.0667(14) Uani 1 1 d . . . C10B C 0.3497(6) 0.53652(18) 0.6750(6) 0.0653(13) Uani 1 1 d . . . C11B C 0.2973(11) 0.5843(2) 0.5983(9) 0.116(2) Uani 1 1 d . . . H11B H 0.2461 0.6108 0.6378 0.140 Uiso 1 1 calc R . . C12B C 0.3204(12) 0.5934(3) 0.4619(9) 0.129(3) Uani 1 1 d . . . H12B H 0.2840 0.6260 0.4116 0.154 Uiso 1 1 calc R . . C13B C 0.3944(9) 0.5560(3) 0.4009(7) 0.0954(19) Uani 1 1 d . . . H13B H 0.4062 0.5623 0.3085 0.114 Uiso 1 1 calc R . . C14B C 0.4505(8) 0.5096(3) 0.4756(8) 0.0884(18) Uani 1 1 d . . . H14B H 0.5061 0.4844 0.4365 0.106 Uiso 1 1 calc R . . C15B C 0.4269(6) 0.4987(2) 0.6108(6) 0.0724(14) Uani 1 1 d . . . H15B H 0.4631 0.4658 0.6588 0.087 Uiso 1 1 calc R . . N1 N 0.0053(8) 0.4061(2) 0.1763(6) 0.123(2) Uani 1 1 d . . . O2 O 0.1643(5) 0.37735(16) 0.5100(4) 0.0805(10) Uani 1 1 d . . . O3 O 0.0877(4) 0.31953(15) 0.1954(4) 0.0765(10) Uani 1 1 d . . . O4 O -0.1963(6) 0.48879(19) 0.0085(5) 0.1129(15) Uani 1 1 d . . . C16 C 0.2295(6) 0.37099(18) 0.4143(6) 0.0581(12) Uani 1 1 d . . . C17 C 0.4130(6) 0.36385(18) 0.4444(5) 0.0565(12) Uani 1 1 d . . . C18 C 0.5267(7) 0.3499(2) 0.5936(6) 0.0665(13) Uani 1 1 d . . . H18 H 0.4830 0.3450 0.6702 0.080 Uiso 1 1 calc R . . C19 C 0.6987(7) 0.3440(2) 0.6226(7) 0.0806(16) Uani 1 1 d . . . H19 H 0.7719 0.3339 0.7202 0.097 Uiso 1 1 calc R . . C20 C 0.7715(8) 0.3519(3) 0.5173(9) 0.0921(19) Uani 1 1 d . . . H20 H 0.8920 0.3488 0.5426 0.111 Uiso 1 1 calc R . . C21 C 0.6616(9) 0.3646(2) 0.3720(8) 0.0858(17) Uani 1 1 d . . . H21 H 0.7081 0.3698 0.2972 0.103 Uiso 1 1 calc R . . C22 C 0.4840(7) 0.3697(2) 0.3354(6) 0.0690(14) Uani 1 1 d . . . H22 H 0.4113 0.3773 0.2357 0.083 Uiso 1 1 calc R . . C23 C 0.0985(7) 0.3658(2) 0.2483(6) 0.0716(14) Uani 1 1 d . . . C24 C -0.152(2) 0.3954(4) 0.0359(10) 0.073(3) Uani 0.59 1 d PD . . H24A H -0.2571 0.3924 0.0587 0.087 Uiso 0.59 1 calc PR . . H24B H -0.1368 0.3627 -0.0139 0.087 Uiso 0.59 1 calc PR . . C25 C -0.159(2) 0.4450(5) -0.0625(14) 0.091(4) Uani 0.59 1 d PD . . H25A H -0.0469 0.4500 -0.0735 0.109 Uiso 0.59 1 calc PR . . H25B H -0.2489 0.4404 -0.1629 0.109 Uiso 0.59 1 calc PR . . C26 C -0.035(2) 0.5037(4) 0.1433(13) 0.083(4) Uani 0.59 1 d PD . . H26A H -0.0503 0.5381 0.1852 0.099 Uiso 0.59 1 calc PR . . H26B H 0.0671 0.5057 0.1152 0.099 Uiso 0.59 1 calc PR . . C27 C -0.015(2) 0.4580(3) 0.2582(11) 0.069(3) Uani 0.59 1 d PD . . H27A H 0.0880 0.4638 0.3499 0.083 Uiso 0.59 1 calc PR . . H27B H -0.1174 0.4558 0.2854 0.083 Uiso 0.59 1 calc PR . . C28 C 0.073(2) 0.4661(7) 0.194(3) 0.103(6) Uani 0.41 1 d PD . . H28A H 0.1061 0.4783 0.1117 0.124 Uiso 0.41 1 calc PR . . H28B H 0.1651 0.4735 0.2921 0.124 Uiso 0.41 1 calc PR . . C29 C -0.2380(19) 0.4252(10) -0.025(3) 0.089(5) Uani 0.41 1 d PD . . H29A H -0.2764 0.4091 0.0509 0.107 Uiso 0.41 1 calc PR . . H29B H -0.3272 0.4195 -0.1250 0.107 Uiso 0.41 1 calc PR . . C30 C -0.0599(16) 0.4024(8) -0.014(2) 0.085(5) Uani 0.41 1 d PD . . H30A H 0.0048 0.4257 -0.0567 0.102 Uiso 0.41 1 calc PR . . H30B H -0.0659 0.3659 -0.0526 0.102 Uiso 0.41 1 calc PR . . C31 C -0.109(2) 0.4860(10) 0.183(2) 0.103(7) Uani 0.41 1 d PD . . H31A H -0.1671 0.4605 0.2260 0.124 Uiso 0.41 1 calc PR . . H31B H -0.1035 0.5210 0.2299 0.124 Uiso 0.41 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 Cl1A 0.0742(8) 0.0986(10) 0.0790(9) 0.0077(8) 0.0348(7) -0.0062(7) O1A 0.068(2) 0.060(2) 0.064(2) -0.0077(16) 0.0298(17) -0.0062(16) C1A 0.070(3) 0.048(3) 0.055(3) -0.004(2) 0.022(2) 0.004(2) C2A 0.062(3) 0.050(3) 0.046(3) 0.002(2) 0.018(2) 0.005(2) C3A 0.059(3) 0.045(2) 0.050(3) 0.000(2) 0.024(2) 0.003(2) C4A 0.066(3) 0.037(2) 0.065(3) -0.003(2) 0.029(2) -0.002(2) C5A 0.078(3) 0.053(3) 0.065(3) 0.005(2) 0.029(3) 0.001(2) C6A 0.097(4) 0.069(3) 0.055(3) 0.011(2) 0.029(3) 0.006(3) C7A 0.085(4) 0.071(3) 0.068(4) 0.011(3) 0.018(3) 0.006(3) C8A 0.066(3) 0.068(3) 0.088(4) 0.004(3) 0.028(3) 0.005(2) C9A 0.069(3) 0.052(3) 0.066(3) -0.002(2) 0.034(3) -0.006(2) C10A 0.057(3) 0.058(3) 0.057(3) -0.010(2) 0.020(2) -0.010(2) C11A 0.070(3) 0.089(4) 0.056(3) -0.004(3) 0.019(3) 0.006(3) C12A 0.097(4) 0.127(6) 0.058(4) -0.024(4) 0.018(3) 0.007(4) C13A 0.109(5) 0.131(6) 0.094(6) -0.060(5) 0.048(4) -0.030(5) C14A 0.165(7) 0.079(4) 0.119(6) -0.059(4) 0.073(6) -0.031(4) C15A 0.119(5) 0.057(3) 0.090(4) -0.013(3) 0.052(4) -0.016(3) Cl1B 0.0900(10) 0.0881(10) 0.0808(10) -0.0169(8) 0.0137(8) -0.0067(8) O1B 0.083(3) 0.067(2) 0.084(3) -0.0202(19) 0.016(2) -0.0097(19) C1B 0.070(3) 0.056(4) 0.055(3) -0.006(2) 0.020(3) 0.001(2) C2B 0.075(3) 0.053(3) 0.057(3) -0.009(2) 0.021(2) -0.003(2) C3B 0.074(3) 0.044(3) 0.068(3) -0.008(2) 0.021(3) -0.010(2) C4B 0.077(4) 0.047(3) 0.059(3) 0.008(2) 0.028(3) 0.005(2) C5B 0.118(5) 0.054(3) 0.068(4) -0.010(3) 0.043(3) -0.005(3) C6B 0.137(6) 0.056(3) 0.083(4) -0.005(3) 0.058(4) 0.009(4) C7B 0.149(7) 0.079(5) 0.117(6) 0.029(4) 0.085(6) 0.031(4) C8B 0.099(4) 0.068(4) 0.079(4) 0.015(3) 0.032(3) 0.016(3) C9B 0.076(4) 0.061(3) 0.066(3) 0.000(2) 0.030(3) 0.004(3) C10B 0.082(3) 0.044(3) 0.076(4) -0.007(3) 0.036(3) -0.008(2) C11B 0.205(8) 0.056(4) 0.119(6) 0.008(4) 0.096(6) 0.011(4) C12B 0.235(10) 0.064(4) 0.127(6) 0.014(4) 0.113(7) 0.004(5) C13B 0.124(5) 0.092(5) 0.081(4) -0.007(4) 0.051(4) -0.032(4) C14B 0.087(4) 0.095(5) 0.082(4) -0.023(4) 0.030(3) -0.011(3) C15B 0.073(3) 0.067(3) 0.070(4) -0.005(3) 0.019(3) 0.005(3) N1 0.158(5) 0.056(3) 0.075(3) -0.010(2) -0.046(3) 0.023(3) O2 0.070(2) 0.102(3) 0.069(2) -0.002(2) 0.027(2) 0.0103(19) O3 0.082(2) 0.072(3) 0.064(2) -0.0100(19) 0.0141(18) 0.0086(19) O4 0.120(3) 0.095(3) 0.083(3) 0.008(3) -0.009(2) 0.046(3) C16 0.061(3) 0.059(3) 0.053(3) -0.001(2) 0.021(3) 0.010(2) C17 0.063(3) 0.059(3) 0.051(3) -0.006(2) 0.025(3) 0.002(2) C18 0.059(3) 0.084(4) 0.052(3) -0.007(3) 0.016(3) 0.000(2) C19 0.066(4) 0.097(4) 0.071(4) -0.015(3) 0.016(3) -0.006(3) C20 0.064(4) 0.101(5) 0.112(6) -0.017(4) 0.035(4) -0.012(3) C21 0.109(5) 0.079(4) 0.102(5) -0.006(4) 0.076(5) -0.007(4) C22 0.076(4) 0.073(3) 0.061(3) -0.009(3) 0.030(3) -0.007(3) C23 0.084(4) 0.057(3) 0.057(3) -0.005(3) 0.006(3) 0.003(3) C24 0.084(8) 0.049(6) 0.054(7) -0.007(5) -0.010(6) 0.002(6) C25 0.108(10) 0.095(10) 0.054(7) 0.037(6) 0.014(7) 0.022(9) C26 0.131(11) 0.038(6) 0.073(8) 0.034(5) 0.032(8) 0.013(7) C27 0.091(8) 0.033(5) 0.063(6) 0.000(4) 0.005(6) 0.018(5) C28 0.099(14) 0.072(13) 0.115(16) 0.000(10) 0.012(11) -0.029(11) C29 0.118(16) 0.071(12) 0.056(11) -0.009(9) 0.007(10) 0.017(12) C30 0.056(10) 0.122(16) 0.064(10) -0.012(10) 0.006(9) -0.023(10) C31 0.15(2) 0.066(13) 0.065(13) -0.017(10) 0.004(12) -0.001(14) _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 Cl1A C9A 1.741(5) . ? O1A C3A 1.424(5) . ? O1A H1A 0.8200 . ? C1A C2A 1.204(6) . ? C1A C1B 1.375(7) . ? C2A C3A 1.479(7) . ? C3A C10A 1.534(6) . ? C3A C4A 1.566(6) . ? C4A C9A 1.363(6) . ? C4A C5A 1.392(6) . ? C5A C6A 1.396(7) . ? C5A H5A 0.9300 . ? C6A C7A 1.348(7) . ? C6A H6A 0.9300 . ? C7A C8A 1.348(7) . ? C7A H7A 0.9300 . ? C8A C9A 1.429(7) . ? C8A H8A 0.9300 . ? C10A C11A 1.386(6) . ? C10A C15A 1.368(7) . ? C11A C12A 1.402(8) . ? C11A H11A 0.9300 . ? C12A C13A 1.337(11) . ? C12A H12A 0.9300 . ? C13A C14A 1.402(10) . ? C13A H13A 0.9300 . ? C14A C15A 1.389(8) . ? C14A H14A 0.9300 . ? C15A H15A 0.9300 . ? Cl1B C9B 1.758(5) . ? O1B C3B 1.445(6) . ? O1B H1B 1.04(7) . ? C1B C2B 1.199(6) . ? C2B C3B 1.476(7) . ? C3B C4B 1.518(7) . ? C3B C10B 1.528(7) . ? C4B C9B 1.379(7) . ? C4B C5B 1.414(7) . ? C5B C6B 1.338(8) . ? C5B H5B 0.9300 . ? C6B C7B 1.380(10) . ? C6B H6B 0.9300 . ? C7B C8B 1.403(9) . ? C7B H7B 0.9300 . ? C8B C9B 1.338(7) . ? C8B H8B 0.9300 . ? C10B C11B 1.375(8) . ? C10B C15B 1.393(7) . ? C11B C12B 1.392(9) . ? C11B H11B 0.9300 . ? C12B C13B 1.352(9) . ? C12B H12B 0.9300 . ? C13B C14B 1.340(9) . ? C13B H13B 0.9300 . ? C14B C15B 1.391(8) . ? C14B H14B 0.9300 . ? C15B H15B 0.9300 . ? N1 C23 1.291(7) . ? N1 C24 1.491(12) . ? N1 C28 1.576(17) . ? N1 C27 1.543(10) . ? N1 C30 1.68(2) . ? O2 C16 1.222(5) . ? O3 C23 1.243(6) . ? O4 C25 1.373(15) . ? O4 C31 1.54(2) . ? O4 C26 1.504(15) . ? O4 C29 1.62(2) . ? C16 C17 1.436(7) . ? C16 C23 1.545(7) . ? C17 C22 1.370(7) . ? C17 C18 1.417(7) . ? C18 C19 1.342(7) . ? C18 H18 0.9300 . ? C19 C20 1.354(8) . ? C19 H19 0.9300 . ? C20 C21 1.372(9) . ? C20 H20 0.9300 . ? C21 C22 1.373(8) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C24 C25 1.533(5) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 C27 1.538(5) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 C31 1.537(5) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 C30 1.536(5) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? 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 H1A 109.5 . . ? C2A C1A C1B 179.0(5) . . ? C1A C2A C3A 176.6(5) . . ? O1A C3A C2A 109.6(3) . . ? O1A C3A C10A 104.1(3) . . ? C2A C3A C10A 113.1(4) . . ? O1A C3A C4A 111.4(3) . . ? C2A C3A C4A 106.5(3) . . ? C10A C3A C4A 112.2(3) . . ? C9A C4A C5A 118.7(4) . . ? C9A C4A C3A 122.0(4) . . ? C5A C4A C3A 119.3(4) . . ? C6A C5A C4A 119.5(5) . . ? C6A C5A H5A 120.2 . . ? C4A C5A H5A 120.2 . . ? C5A C6A C7A 121.0(5) . . ? C5A C6A H6A 119.5 . . ? C7A C6A H6A 119.5 . . ? C8A C7A C6A 121.3(5) . . ? C8A C7A H7A 119.4 . . ? C6A C7A H7A 119.4 . . ? C7A C8A C9A 118.6(5) . . ? C7A C8A H8A 120.7 . . ? C9A C8A H8A 120.7 . . ? C4A C9A C8A 121.0(4) . . ? C4A C9A Cl1A 122.8(4) . . ? C8A C9A Cl1A 116.1(4) . . ? C11A C10A C15A 120.4(5) . . ? C11A C10A C3A 120.3(4) . . ? C15A C10A C3A 119.3(4) . . ? C10A C11A C12A 117.5(6) . . ? C10A C11A H11A 121.2 . . ? C12A C11A H11A 121.2 . . ? C13A C12A C11A 122.1(6) . . ? C13A C12A H12A 119.0 . . ? C11A C12A H12A 119.0 . . ? C12A C13A C14A 120.8(6) . . ? C12A C13A H13A 119.6 . . ? C14A C13A H13A 119.6 . . ? C15A C14A C13A 117.3(7) . . ? C15A C14A H14A 121.3 . . ? C13A C14A H14A 121.3 . . ? C14A C15A C10A 121.7(6) . . ? C14A C15A H15A 119.1 . . ? C10A C15A H15A 119.1 . . ? C3B O1B H1B 109(4) . . ? C2B C1B C1A 178.7(5) . . ? C1B C2B C3B 177.6(5) . . ? O1B C3B C2B 108.1(4) . . ? O1B C3B C4B 107.0(4) . . ? C2B C3B C4B 109.9(4) . . ? O1B C3B C10B 107.4(4) . . ? C2B C3B C10B 111.7(4) . . ? C4B C3B C10B 112.4(4) . . ? C9B C4B C5B 115.7(5) . . ? C9B C4B C3B 123.7(4) . . ? C5B C4B C3B 120.5(5) . . ? C6B C5B C4B 121.9(6) . . ? C6B C5B H5B 119.1 . . ? C4B C5B H5B 119.1 . . ? C5B C6B C7B 120.6(6) . . ? C5B C6B H6B 119.7 . . ? C7B C6B H6B 119.7 . . ? C8B C7B C6B 118.9(6) . . ? C8B C7B H7B 120.6 . . ? C6B C7B H7B 120.6 . . ? C7B C8B C9B 119.1(6) . . ? C7B C8B H8B 120.5 . . ? C9B C8B H8B 120.5 . . ? C8B C9B C4B 123.8(5) . . ? C8B C9B Cl1B 116.3(5) . . ? C4B C9B Cl1B 120.0(4) . . ? C11B C10B C15B 117.0(5) . . ? C11B C10B C3B 121.1(5) . . ? C15B C10B C3B 121.8(5) . . ? C10B C11B C12B 120.4(6) . . ? C10B C11B H11B 119.8 . . ? C12B C11B H11B 119.8 . . ? C13B C12B C11B 121.6(7) . . ? C13B C12B H12B 119.2 . . ? C11B C12B H12B 119.2 . . ? C14B C13B C12B 119.1(6) . . ? C14B C13B H13B 120.5 . . ? C12B C13B H13B 120.5 . . ? C13B C14B C15B 120.9(6) . . ? C13B C14B H14B 119.5 . . ? C15B C14B H14B 119.5 . . ? C14B C15B C10B 120.9(5) . . ? C14B C15B H15B 119.5 . . ? C10B C15B H15B 119.5 . . ? C23 N1 C24 118.5(6) . . ? C23 N1 C28 124.2(8) . . ? C24 N1 C28 114.7(9) . . ? C23 N1 C27 122.4(6) . . ? C24 N1 C27 112.3(8) . . ? C28 N1 C27 41.9(7) . . ? C23 N1 C30 114.4(7) . . ? C24 N1 C30 37.7(5) . . ? C28 N1 C30 97.4(12) . . ? C27 N1 C30 122.3(8) . . ? C25 O4 C31 113.0(9) . . ? C25 O4 C26 108.9(9) . . ? C31 O4 C26 35.8(7) . . ? C25 O4 C29 37.2(6) . . ? C31 O4 C29 98.3(13) . . ? C26 O4 C29 117.4(8) . . ? O2 C16 C17 125.8(4) . . ? O2 C16 C23 115.8(5) . . ? C17 C16 C23 118.2(5) . . ? C22 C17 C18 118.1(5) . . ? C22 C17 C16 123.1(5) . . ? C18 C17 C16 118.8(5) . . ? C19 C18 C17 118.9(5) . . ? C19 C18 H18 120.5 . . ? C17 C18 H18 120.5 . . ? C20 C19 C18 123.5(6) . . ? C20 C19 H19 118.2 . . ? C18 C19 H19 118.2 . . ? C19 C20 C21 117.9(5) . . ? C19 C20 H20 121.1 . . ? C21 C20 H20 121.1 . . ? C20 C21 C22 120.9(5) . . ? C20 C21 H21 119.5 . . ? C22 C21 H21 119.5 . . ? C21 C22 C17 120.6(5) . . ? C21 C22 H22 119.7 . . ? C17 C22 H22 119.7 . . ? O3 C23 N1 124.4(5) . . ? O3 C23 C16 114.0(4) . . ? N1 C23 C16 121.5(5) . . ? N1 C24 C25 102.9(9) . . ? N1 C24 H24A 111.2 . . ? C25 C24 H24A 111.2 . . ? N1 C24 H24B 111.2 . . ? C25 C24 H24B 111.2 . . ? H24A C24 H24B 109.1 . . ? O4 C25 C24 107.7(12) . . ? O4 C25 H25A 110.2 . . ? C24 C25 H25A 110.2 . . ? O4 C25 H25B 110.2 . . ? C24 C25 H25B 110.2 . . ? H25A C25 H25B 108.5 . . ? O4 C26 C27 104.4(10) . . ? O4 C26 H26A 110.9 . . ? C27 C26 H26A 110.9 . . ? O4 C26 H26B 110.9 . . ? C27 C26 H26B 110.9 . . ? H26A C26 H26B 108.9 . . ? N1 C27 C26 105.3(8) . . ? N1 C27 H27A 110.7 . . ? C26 C27 H27A 110.7 . . ? N1 C27 H27B 110.7 . . ? C26 C27 H27B 110.7 . . ? H27A C27 H27B 108.8 . . ? N1 C28 C31 90.2(14) . . ? N1 C28 H28A 113.6 . . ? C31 C28 H28A 113.6 . . ? N1 C28 H28B 113.6 . . ? C31 C28 H28B 113.6 . . ? H28A C28 H28B 110.9 . . ? C30 C29 O4 102.7(15) . . ? C30 C29 H29A 111.2 . . ? O4 C29 H29A 111.2 . . ? C30 C29 H29B 111.2 . . ? O4 C29 H29B 111.2 . . ? H29A C29 H29B 109.1 . . ? C29 C30 N1 88.0(14) . . ? C29 C30 H30A 114.0 . . ? N1 C30 H30A 114.0 . . ? C29 C30 H30B 114.0 . . ? N1 C30 H30B 114.0 . . ? H30A C30 H30B 111.2 . . ? O4 C31 C28 98.2(15) . . ? O4 C31 H31A 112.1 . . ? C28 C31 H31A 112.1 . . ? O4 C31 H31B 112.1 . . ? C28 C31 H31B 112.1 . . ? H31A C31 H31B 109.8 . . ? 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 C1B C1A C2A C3A 146(25) . . . . ? C1A C2A C3A O1A 34(8) . . . . ? C1A C2A C3A C10A 150(8) . . . . ? C1A C2A C3A C4A -86(8) . . . . ? O1A C3A C4A C9A 175.4(4) . . . . ? C2A C3A C4A C9A -65.2(5) . . . . ? C10A C3A C4A C9A 59.1(5) . . . . ? O1A C3A C4A C5A -7.8(5) . . . . ? C2A C3A C4A C5A 111.7(4) . . . . ? C10A C3A C4A C5A -124.1(4) . . . . ? C9A C4A C5A C6A -0.1(6) . . . . ? C3A C4A C5A C6A -177.0(4) . . . . ? C4A C5A C6A C7A 0.4(7) . . . . ? C5A C6A C7A C8A -1.7(8) . . . . ? C6A C7A C8A C9A 2.5(8) . . . . ? C5A C4A C9A C8A 1.0(6) . . . . ? C3A C4A C9A C8A 177.9(4) . . . . ? C5A C4A C9A Cl1A 179.4(3) . . . . ? C3A C4A C9A Cl1A -3.7(6) . . . . ? C7A C8A C9A C4A -2.2(7) . . . . ? C7A C8A C9A Cl1A 179.2(4) . . . . ? O1A C3A C10A C11A 99.3(4) . . . . ? C2A C3A C10A C11A -19.5(5) . . . . ? C4A C3A C10A C11A -140.0(4) . . . . ? O1A C3A C10A C15A -78.6(5) . . . . ? C2A C3A C10A C15A 162.6(4) . . . . ? C4A C3A C10A C15A 42.1(6) . . . . ? C15A C10A C11A C12A -0.6(7) . . . . ? C3A C10A C11A C12A -178.5(4) . . . . ? C10A C11A C12A C13A 1.7(8) . . . . ? C11A C12A C13A C14A -2.9(10) . . . . ? C12A C13A C14A C15A 2.8(10) . . . . ? C13A C14A C15A C10A -1.7(9) . . . . ? C11A C10A C15A C14A 0.7(8) . . . . ? C3A C10A C15A C14A 178.6(5) . . . . ? C2A C1A C1B C2B 91(37) . . . . ? C1A C1B C2B C3B -3(35) . . . . ? C1B C2B C3B O1B -148(13) . . . . ? C1B C2B C3B C4B 96(13) . . . . ? C1B C2B C3B C10B -30(13) . . . . ? O1B C3B C4B C9B -177.2(4) . . . . ? C2B C3B C4B C9B -60.1(6) . . . . ? C10B C3B C4B C9B 65.1(5) . . . . ? O1B C3B C4B C5B 4.5(6) . . . . ? C2B C3B C4B C5B 121.7(5) . . . . ? C10B C3B C4B C5B -113.2(5) . . . . ? C9B C4B C5B C6B 0.4(7) . . . . ? C3B C4B C5B C6B 178.8(5) . . . . ? C4B C5B C6B C7B 1.7(9) . . . . ? C5B C6B C7B C8B -2.3(9) . . . . ? C6B C7B C8B C9B 0.8(8) . . . . ? C7B C8B C9B C4B 1.4(8) . . . . ? C7B C8B C9B Cl1B -178.9(4) . . . . ? C5B C4B C9B C8B -2.0(7) . . . . ? C3B C4B C9B C8B 179.7(5) . . . . ? C5B C4B C9B Cl1B 178.3(4) . . . . ? C3B C4B C9B Cl1B 0.0(7) . . . . ? O1B C3B C10B C11B -85.7(7) . . . . ? C2B C3B C10B C11B 155.9(6) . . . . ? C4B C3B C10B C11B 31.8(7) . . . . ? O1B C3B C10B C15B 89.6(5) . . . . ? C2B C3B C10B C15B -28.8(7) . . . . ? C4B C3B C10B C15B -152.9(5) . . . . ? C15B C10B C11B C12B 0.6(10) . . . . ? C3B C10B C11B C12B 176.0(6) . . . . ? C10B C11B C12B C13B -0.1(12) . . . . ? C11B C12B C13B C14B -1.6(12) . . . . ? C12B C13B C14B C15B 2.7(10) . . . . ? C13B C14B C15B C10B -2.3(8) . . . . ? C11B C10B C15B C14B 0.6(8) . . . . ? C3B C10B C15B C14B -174.9(5) . . . . ? O2 C16 C17 C22 -163.8(5) . . . . ? C23 C16 C17 C22 21.5(7) . . . . ? O2 C16 C17 C18 16.3(7) . . . . ? C23 C16 C17 C18 -158.4(4) . . . . ? C22 C17 C18 C19 1.1(7) . . . . ? C16 C17 C18 C19 -179.0(5) . . . . ? C17 C18 C19 C20 1.6(9) . . . . ? C18 C19 C20 C21 -2.6(9) . . . . ? C19 C20 C21 C22 0.8(10) . . . . ? C20 C21 C22 C17 1.9(9) . . . . ? C18 C17 C22 C21 -2.8(7) . . . . ? C16 C17 C22 C21 177.3(5) . . . . ? C24 N1 C23 O3 14.1(12) . . . . ? C28 N1 C23 O3 -146.5(12) . . . . ? C27 N1 C23 O3 162.9(8) . . . . ? C30 N1 C23 O3 -27.9(11) . . . . ? C24 N1 C23 C16 -163.0(8) . . . . ? C28 N1 C23 C16 36.4(15) . . . . ? C27 N1 C23 C16 -14.2(12) . . . . ? C30 N1 C23 C16 154.9(8) . . . . ? O2 C16 C23 O3 -108.2(5) . . . . ? C17 C16 C23 O3 67.0(6) . . . . ? O2 C16 C23 N1 69.2(8) . . . . ? C17 C16 C23 N1 -115.6(6) . . . . ? C23 N1 C24 C25 -147.2(12) . . . . ? C28 N1 C24 C25 15.2(18) . . . . ? C27 N1 C24 C25 61.0(15) . . . . ? C30 N1 C24 C25 -53.5(11) . . . . ? C31 O4 C25 C24 36.4(18) . . . . ? C26 O4 C25 C24 74.6(15) . . . . ? C29 O4 C25 C24 -36.1(10) . . . . ? N1 C24 C25 O4 -66.5(17) . . . . ? C25 O4 C26 C27 -70.7(13) . . . . ? C31 O4 C26 C27 32.7(12) . . . . ? C29 O4 C26 C27 -31.2(16) . . . . ? C23 N1 C27 C26 148.2(11) . . . . ? C24 N1 C27 C26 -61.3(14) . . . . ? C28 N1 C27 C26 41.4(11) . . . . ? C30 N1 C27 C26 -20.1(16) . . . . ? O4 C26 C27 N1 59.6(14) . . . . ? C23 N1 C28 C31 -142.2(12) . . . . ? C24 N1 C28 C31 56.5(18) . . . . ? C27 N1 C28 C31 -39.9(9) . . . . ? C30 N1 C28 C31 91.6(15) . . . . ? C25 O4 C29 C30 37.6(10) . . . . ? C31 O4 C29 C30 -79.9(18) . . . . ? C26 O4 C29 C30 -48(2) . . . . ? O4 C29 C30 N1 77.3(16) . . . . ? C23 N1 C30 C29 140.1(14) . . . . ? C24 N1 C30 C29 34.4(8) . . . . ? C28 N1 C30 C29 -87.1(16) . . . . ? C27 N1 C30 C29 -50.8(18) . . . . ? C25 O4 C31 C28 43.2(19) . . . . ? C26 O4 C31 C28 -47.5(12) . . . . ? C29 O4 C31 C28 78.8(15) . . . . ? N1 C28 C31 O4 -85.4(17) . . . . ? _diffrn_measured_fraction_theta_max 0.930 _diffrn_reflns_theta_full 27.35 _diffrn_measured_fraction_theta_full 0.930 _refine_diff_density_max 0.327 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.059 # Attachment 'Ib.cif' data_Ib'' _database_code_depnum_ccdc_archive 'CCDC 664464' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C34H34O4), (C13H15NO2)' _chemical_formula_sum 'C47 H49 N O6' _chemical_formula_weight 723.87 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 monoclinic _symmetry_space_group_name_H-M P21 _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.42040(10) _cell_length_b 41.0982(6) _cell_length_c 10.1701(2) _cell_angle_alpha 90.00 _cell_angle_beta 91.8046(7) _cell_angle_gamma 90.00 _cell_volume 3935.52(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _chemical_absolute_configuration unk _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.222 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1544 _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_% ? _diffrn_reflns_number 11991 _diffrn_reflns_av_R_equivalents 0.0531 _diffrn_reflns_av_sigmaI/netI 0.1417 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -48 _diffrn_reflns_limit_k_max 47 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 25.04 _reflns_number_total 6620 _reflns_number_gt 2889 _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^)+(0.1082P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6620 _refine_ls_number_parameters 763 _refine_ls_number_restraints 25 _refine_ls_R_factor_all 0.1674 _refine_ls_R_factor_gt 0.0744 _refine_ls_wR_factor_ref 0.2211 _refine_ls_wR_factor_gt 0.1915 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.816 _refine_ls_shift/su_mean 0.082 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 0.9678(6) 0.56215(16) 0.6275(5) 0.0761(19) Uani 1 1 d . . . H1OA H 1.0193 0.5535 0.6839 0.114 Uiso 1 1 calc R . . O2A O 1.1306(6) 0.53737(15) 0.8179(6) 0.0703(17) Uani 1 1 d . . . H2OA H 1.1987 0.5249 0.8179 0.105 Uiso 1 1 calc R . . O3A O 0.8475(6) 0.61532(14) 0.8937(5) 0.0554(15) Uani 1 1 d . . . O4A O 1.0527(6) 0.60638(15) 1.0142(5) 0.0595(16) Uani 1 1 d . . . C1A C 0.9152(8) 0.5876(2) 0.8375(8) 0.051(2) Uani 1 1 d . . . H1A H 0.8667 0.5678 0.8658 0.061 Uiso 1 1 calc R . . C2A C 0.9000(9) 0.5904(2) 0.6827(8) 0.055(2) Uani 1 1 d . . . C3A C 0.9640(7) 0.62140(14) 0.6316(5) 0.050(2) Uani 1 1 d G . . C4A C 0.8891(6) 0.65045(18) 0.6388(5) 0.063(3) Uani 1 1 d G . . H4A H 0.7982 0.6506 0.6720 0.076 Uiso 1 1 calc R . . C5A C 0.9499(10) 0.67925(14) 0.5963(7) 0.090(4) Uani 1 1 d G . . H5A H 0.8998 0.6987 0.6011 0.108 Uiso 1 1 calc R . . C6A C 1.0857(10) 0.6790(2) 0.5466(6) 0.104(4) Uani 1 1 d G . . H6A H 1.1264 0.6983 0.5182 0.125 Uiso 1 1 calc R . . C7A C 1.1606(6) 0.6499(3) 0.5394(6) 0.095(4) Uani 1 1 d G . . H7A H 1.2515 0.6498 0.5062 0.114 Uiso 1 1 calc R . . C8A C 1.0997(6) 0.6211(2) 0.5819(6) 0.084(3) Uani 1 1 d G . . H8A H 1.1499 0.6017 0.5770 0.101 Uiso 1 1 calc R . . C9A C 0.7412(5) 0.58756(15) 0.6334(6) 0.053(2) Uani 1 1 d G . . C10A C 0.6272(7) 0.58474(16) 0.7162(4) 0.067(3) Uani 1 1 d G . . H10A H 0.6424 0.5855 0.8069 0.080 Uiso 1 1 calc R . . C11A C 0.4904(5) 0.58082(18) 0.6633(7) 0.076(3) Uani 1 1 d G . . H11A H 0.4141 0.5789 0.7186 0.091 Uiso 1 1 calc R . . C12A C 0.4676(5) 0.57972(18) 0.5276(7) 0.082(3) Uani 1 1 d G . . H12A H 0.3761 0.5771 0.4922 0.098 Uiso 1 1 calc R . . C13A C 0.5817(7) 0.58254(18) 0.4449(5) 0.078(3) Uani 1 1 d G . . H13A H 0.5664 0.5818 0.3541 0.094 Uiso 1 1 calc R . . C14A C 0.7185(6) 0.58646(16) 0.4978(5) 0.072(3) Uani 1 1 d G . . H14A H 0.7947 0.5884 0.4424 0.086 Uiso 1 1 calc R . . C15A C 1.0667(8) 0.5879(2) 0.8982(8) 0.051(2) Uani 1 1 d . . . H15A H 1.1307 0.5990 0.8389 0.061 Uiso 1 1 calc R . . C16A C 1.1306(9) 0.5547(2) 0.9389(9) 0.057(2) Uani 1 1 d . . . C17A C 1.0410(7) 0.53667(19) 1.0412(8) 0.070(3) Uani 1 1 d G . . C18A C 1.0409(8) 0.54751(18) 1.1706(9) 0.085(3) Uani 1 1 d G . . H18A H 1.0978 0.5650 1.1967 0.102 Uiso 1 1 calc R . . C19A C 0.9556(10) 0.5322(3) 1.2611(7) 0.139(6) Uani 1 1 d G . . H19A H 0.9555 0.5395 1.3477 0.167 Uiso 1 1 calc R . . C20A C 0.8704(8) 0.5061(3) 1.2221(12) 0.147(8) Uani 1 1 d G . . H20A H 0.8134 0.4959 1.2827 0.176 Uiso 1 1 calc R . . C21A C 0.8706(7) 0.49529(18) 1.0927(13) 0.135(6) Uani 1 1 d G . . H21A H 0.8136 0.4778 1.0666 0.162 Uiso 1 1 calc R . . C22A C 0.9559(9) 0.5106(2) 1.0022(8) 0.095(4) Uani 1 1 d G . . H22A H 0.9586 0.5027 0.9153 0.114 Uiso 1 1 d R . . C23A C 1.2867(4) 0.55764(16) 0.9913(5) 0.052(2) Uani 1 1 d G . . C24A C 1.3619(7) 0.52875(13) 1.0079(7) 0.086(3) Uani 1 1 d G . . H24A H 1.3171 0.5089 0.9916 0.103 Uiso 1 1 calc R . . C25A C 1.5041(7) 0.52950(17) 1.0487(7) 0.096(4) Uani 1 1 d G . . H25A H 1.5544 0.5102 1.0598 0.115 Uiso 1 1 calc R . . C26A C 1.5711(5) 0.5591(2) 1.0730(6) 0.076(3) Uani 1 1 d G . . H26A H 1.6662 0.5596 1.1004 0.091 Uiso 1 1 calc R . . C27A C 1.4959(7) 0.58801(16) 1.0565(6) 0.072(3) Uani 1 1 d G . . H27A H 1.5407 0.6078 1.0727 0.087 Uiso 1 1 calc R . . C28A C 1.3537(6) 0.58727(13) 1.0156(6) 0.064(3) Uani 1 1 d G . . H28A H 1.3034 0.6066 1.0045 0.076 Uiso 1 1 calc R . . C29A C 0.9406(9) 0.6292(2) 0.9948(7) 0.048(2) Uani 1 1 d . . . C30A C 0.8579(9) 0.6316(2) 1.1201(8) 0.064(3) Uani 1 1 d . . . H30C H 0.8308 0.6100 1.1479 0.076 Uiso 1 1 calc R . . H30D H 0.7719 0.6441 1.1031 0.076 Uiso 1 1 calc R . . C31A C 0.9481(10) 0.6482(3) 1.2312(8) 0.072(3) Uani 1 1 d . . . H31C H 0.8910 0.6507 1.3083 0.086 Uiso 1 1 calc R . . H31D H 1.0284 0.6344 1.2551 0.086 Uiso 1 1 calc R . . C32A C 1.0001(10) 0.6805(2) 1.1891(10) 0.076(3) Uani 1 1 d . . . H32C H 1.0602 0.6898 1.2586 0.091 Uiso 1 1 calc R . . H32D H 0.9199 0.6949 1.1736 0.091 Uiso 1 1 calc R . . C33A C 1.0838(9) 0.6775(2) 1.0640(9) 0.067(3) Uani 1 1 d . . . H33C H 1.1135 0.6990 1.0369 0.080 Uiso 1 1 calc R . . H33D H 1.1686 0.6647 1.0824 0.080 Uiso 1 1 calc R . . C34A C 0.9983(9) 0.6617(2) 0.9518(8) 0.056(2) Uani 1 1 d . . . H34C H 0.9203 0.6758 0.9247 0.067 Uiso 1 1 calc R . . H34D H 1.0584 0.6586 0.8771 0.067 Uiso 1 1 calc R . . O5A O 0.9281(17) 0.9293(4) 0.4884(14) 0.132(10) Uiso 0.55(3) 1 d PD . . O6A O 0.7826(9) 0.9760(2) 0.2284(9) 0.125(3) Uiso 1 1 d D . . N1A N 0.7874(14) 0.9726(3) 0.4524(13) 0.162(5) Uiso 1 1 d D . . C35A C 1.0813(11) 0.9498(4) 0.3251(10) 0.117(4) Uani 1 1 d GD . . C36A C 1.1677(18) 0.9273(2) 0.2645(11) 0.146(6) Uani 1 1 d G . . H36A H 1.1323 0.9068 0.2422 0.175 Uiso 1 1 calc R . . C37A C 1.3071(16) 0.9353(4) 0.2374(10) 0.226(13) Uani 1 1 d G . . H37A H 1.3649 0.9202 0.1969 0.271 Uiso 1 1 calc R . . C38A C 1.3601(11) 0.9659(5) 0.2707(12) 0.179(9) Uani 1 1 d G . . H38A H 1.4533 0.9712 0.2526 0.214 Uiso 1 1 calc R . . C39A C 1.2736(17) 0.9884(3) 0.3313(12) 0.159(8) Uani 1 1 d G . . H39A H 1.3091 1.0089 0.3536 0.191 Uiso 1 1 calc R . . C40A C 1.1343(15) 0.9804(3) 0.3584(9) 0.141(6) Uani 1 1 d G . . H40A H 1.0764 0.9955 0.3989 0.170 Uiso 1 1 calc R . . C41A C 0.9361(13) 0.9392(4) 0.3532(14) 0.130(5) Uiso 1 1 d D . . H41A H 0.9103 0.9208 0.2961 0.156 Uiso 1 1 calc R . . C42A C 0.8279(14) 0.9655(3) 0.3347(12) 0.123(4) Uiso 1 1 d D . . C43A C 0.868(2) 0.9554(4) 0.5579(16) 0.193(8) Uiso 1 1 d D . . H43A H 0.9415 0.9695 0.5976 0.232 Uiso 1 1 calc R . . C44A C 0.771(2) 0.9433(5) 0.658(2) 0.210(8) Uiso 1 1 d D . . H44C H 0.8242 0.9332 0.7308 0.251 Uiso 1 1 calc R . . H44D H 0.7053 0.9274 0.6206 0.251 Uiso 1 1 calc R . . C45A C 0.692(2) 0.9730(5) 0.7047(19) 0.205(8) Uiso 1 1 d D . . H45C H 0.7596 0.9888 0.7398 0.246 Uiso 1 1 calc R . . H45D H 0.6298 0.9668 0.7746 0.246 Uiso 1 1 calc R . . C46A C 0.6046(19) 0.9883(5) 0.5923(17) 0.188(7) Uiso 1 1 d D . . H46C H 0.5369 0.9725 0.5574 0.225 Uiso 1 1 calc R . . H46D H 0.5516 1.0066 0.6256 0.225 Uiso 1 1 calc R . . C47A C 0.696(2) 0.9997(4) 0.4844(19) 0.205(8) Uiso 1 1 d D . . H47C H 0.6385 1.0060 0.4081 0.246 Uiso 1 1 calc R . . H47D H 0.7528 1.0182 0.5132 0.246 Uiso 1 1 calc R . . O1B O 0.3729(6) 0.81556(15) 0.0740(6) 0.0704(18) Uani 1 1 d . . . H1OB H 0.3223 0.8317 0.0805 0.106 Uiso 1 1 calc R . . O2B O 0.5197(6) 0.78866(15) -0.1129(5) 0.0668(17) Uani 1 1 d . . . H2OB H 0.4533 0.7939 -0.0671 0.100 Uiso 1 1 calc R . . O3B O 0.4567(6) 0.74533(14) 0.2716(5) 0.0577(15) Uani 1 1 d . . . O4B O 0.6596(5) 0.73897(13) 0.1615(5) 0.0512(14) Uani 1 1 d . . . C1B C 0.4398(8) 0.7644(2) 0.1584(8) 0.048(2) Uani 1 1 d . . . H1B H 0.3727 0.7538 0.0968 0.058 Uiso 1 1 calc R . . C2B C 0.3786(9) 0.7980(2) 0.1994(8) 0.058(2) Uani 1 1 d . . . C3B C 0.2244(5) 0.79558(16) 0.2490(6) 0.056(2) Uani 1 1 d G . . C4B C 0.1605(6) 0.76653(13) 0.2845(6) 0.068(3) Uani 1 1 d G . . H4B H 0.2109 0.7471 0.2808 0.082 Uiso 1 1 calc R . . C5B C 0.0211(6) 0.76650(16) 0.3256(7) 0.076(3) Uani 1 1 d G . . H5B H -0.0216 0.7471 0.3494 0.091 Uiso 1 1 calc R . . C6B C -0.0543(5) 0.7955(2) 0.3312(6) 0.085(3) Uani 1 1 d G . . H6B H -0.1475 0.7955 0.3587 0.102 Uiso 1 1 calc R . . C7B C 0.0096(7) 0.82456(16) 0.2957(7) 0.086(3) Uani 1 1 d G . . H7B H -0.0408 0.8440 0.2994 0.104 Uiso 1 1 calc R . . C8B C 0.1490(7) 0.82459(13) 0.2546(7) 0.081(3) Uani 1 1 d G . . H8B H 0.1917 0.8440 0.2308 0.098 Uiso 1 1 calc R . . C9B C 0.4715(7) 0.81628(17) 0.2994(7) 0.066(3) Uani 1 1 d G . . C10B C 0.4750(9) 0.80596(17) 0.4296(9) 0.093(4) Uani 1 1 d G . . H10B H 0.4189 0.7886 0.4547 0.111 Uiso 1 1 calc R . . C11B C 0.5623(11) 0.8217(3) 0.5222(7) 0.119(5) Uani 1 1 d G . . H11B H 0.5647 0.8147 0.6094 0.143 Uiso 1 1 calc R . . C12B C 0.6462(8) 0.8477(3) 0.4847(11) 0.154(8) Uani 1 1 d G . . H12B H 0.7046 0.8582 0.5466 0.184 Uiso 1 1 calc R . . C13B C 0.6427(8) 0.85799(18) 0.3544(12) 0.148(7) Uani 1 1 d G . . H13B H 0.6988 0.8754 0.3293 0.177 Uiso 1 1 calc R . . C14B C 0.5553(9) 0.84229(19) 0.2618(8) 0.100(4) Uani 1 1 d G . . H14B H 0.5530 0.8492 0.1747 0.120 Uiso 1 1 calc R . . C15B C 0.5877(8) 0.7651(2) 0.0988(8) 0.053(2) Uani 1 1 d . . . H15B H 0.6349 0.7853 0.1263 0.063 Uiso 1 1 calc R . . C16B C 0.5945(8) 0.7625(2) -0.0530(7) 0.048(2) Uani 1 1 d . . . C17B C 0.5287(6) 0.72959(13) -0.1027(6) 0.052(2) Uani 1 1 d G . . C18B C 0.6093(5) 0.70125(17) -0.0996(6) 0.062(2) Uani 1 1 d G . . H18B H 0.7035 0.7018 -0.0694 0.074 Uiso 1 1 calc R . . C19B C 0.5491(8) 0.67202(13) -0.1416(6) 0.063(2) Uani 1 1 d G . . H19B H 0.6030 0.6531 -0.1395 0.075 Uiso 1 1 calc R . . C20B C 0.4083(8) 0.67112(16) -0.1867(6) 0.085(3) Uani 1 1 d G . . H20B H 0.3680 0.6516 -0.2147 0.102 Uiso 1 1 calc R . . C21B C 0.3277(5) 0.6995(2) -0.1898(6) 0.082(3) Uani 1 1 d G . . H21B H 0.2335 0.6989 -0.2199 0.098 Uiso 1 1 calc R . . C22B C 0.3879(6) 0.72869(16) -0.1478(6) 0.074(3) Uani 1 1 d G . . H22B H 0.3340 0.7477 -0.1498 0.089 Uiso 1 1 calc R . . C23B C 0.7490(5) 0.76461(15) -0.1043(6) 0.054(2) Uani 1 1 d G . . C24B C 0.7622(6) 0.76622(16) -0.2399(5) 0.062(2) Uani 1 1 d G . . H24B H 0.6820 0.7646 -0.2952 0.075 Uiso 1 1 calc R . . C25B C 0.8953(8) 0.77024(18) -0.2929(5) 0.080(3) Uani 1 1 d G . . H25B H 0.9041 0.7713 -0.3836 0.096 Uiso 1 1 calc R . . C26B C 1.0152(5) 0.77264(19) -0.2103(7) 0.084(3) Uani 1 1 d G . . H26B H 1.1043 0.7753 -0.2457 0.101 Uiso 1 1 calc R . . C27B C 1.0021(5) 0.77103(19) -0.0747(7) 0.084(3) Uani 1 1 d G . . H27B H 1.0823 0.7726 -0.0194 0.100 Uiso 1 1 calc R . . C28B C 0.8690(7) 0.76701(16) -0.0217(4) 0.065(2) Uani 1 1 d G . . H28B H 0.8600 0.7651 0.0698 0.078 Uiso 1 1 d R . . C29B C 0.5759(8) 0.7241(2) 0.2617(8) 0.050(2) Uani 1 1 d . . . C30B C 0.5287(9) 0.6906(2) 0.2208(8) 0.055(2) Uani 1 1 d . . . H30E H 0.4688 0.6922 0.1417 0.066 Uiso 1 1 calc R . . H30F H 0.6112 0.6777 0.2004 0.066 Uiso 1 1 calc R . . C31B C 0.4482(9) 0.6739(2) 0.3261(8) 0.068(3) Uani 1 1 d . . . H31E H 0.4251 0.6519 0.2985 0.081 Uiso 1 1 calc R . . H31F H 0.3600 0.6854 0.3400 0.081 Uiso 1 1 calc R . . C32B C 0.5374(10) 0.6729(2) 0.4551(9) 0.066(3) Uani 1 1 d . . . H32E H 0.4835 0.6627 0.5235 0.080 Uiso 1 1 calc R . . H32F H 0.6227 0.6602 0.4430 0.080 Uiso 1 1 calc R . . C33B C 0.5757(10) 0.7061(3) 0.4945(8) 0.068(3) Uani 1 1 d . . . H33E H 0.6325 0.7052 0.5756 0.081 Uiso 1 1 calc R . . H33F H 0.4897 0.7180 0.5121 0.081 Uiso 1 1 calc R . . C34B C 0.6582(9) 0.7244(2) 0.3919(8) 0.056(2) Uani 1 1 d . . . H34E H 0.6734 0.7467 0.4204 0.067 Uiso 1 1 calc R . . H34F H 0.7502 0.7143 0.3817 0.067 Uiso 1 1 calc R . . C35B C 0.5815(11) 0.9023(3) 0.9333(10) 0.113(5) Uani 1 1 d GD . . C36B C 0.6740(18) 0.9248(2) 0.9915(11) 0.161(7) Uani 1 1 d G . . H36B H 0.6416 0.9455 1.0127 0.193 Uiso 1 1 calc R . . C37B C 0.8149(16) 0.9164(4) 1.0180(10) 0.158(8) Uani 1 1 d G . . H37B H 0.8768 0.9315 1.0569 0.189 Uiso 1 1 calc R . . C38B C 0.8634(10) 0.8856(4) 0.9863(11) 0.163(8) Uani 1 1 d G . . H38B H 0.9577 0.8799 1.0041 0.195 Uiso 1 1 calc R . . C39B C 0.7709(16) 0.8631(2) 0.9281(11) 0.159(7) Uani 1 1 d G . . H39B H 0.8033 0.8424 0.9069 0.191 Uiso 1 1 calc R . . C40B C 0.6299(14) 0.8714(3) 0.9016(9) 0.120(5) Uani 1 1 d G . . H40B H 0.5680 0.8564 0.8627 0.143 Uiso 1 1 calc R . . O5B O 0.4199(19) 0.9233(5) 0.7696(14) 0.135(9) Uiso 0.52(2) 1 d PD . . O6B O 0.2888(10) 0.8768(2) 1.0253(9) 0.132(3) Uiso 1 1 d D . . N1B N 0.281(2) 0.8876(5) 0.7963(17) 0.244(8) Uiso 1 1 d D . . C41B C 0.4357(12) 0.9139(4) 0.9042(14) 0.130(5) Uiso 1 1 d D . . H41B H 0.4147 0.9324 0.9609 0.156 Uiso 1 1 calc R . . C42B C 0.3265(16) 0.8881(4) 0.9198(14) 0.143(5) Uiso 1 1 d D . . C43B C 0.373(2) 0.8967(5) 0.690(2) 0.215(9) Uiso 1 1 d D . . H43B H 0.4413 0.8812 0.6553 0.258 Uiso 1 1 calc R . . C44B C 0.257(2) 0.9099(5) 0.606(2) 0.244(10) Uiso 1 1 d D . . H44E H 0.2918 0.9243 0.5382 0.293 Uiso 1 1 calc R . . H44F H 0.1863 0.9211 0.6562 0.293 Uiso 1 1 calc R . . C45B C 0.202(2) 0.8778(5) 0.550(2) 0.221(9) Uiso 1 1 d D . . H45E H 0.2804 0.8635 0.5298 0.266 Uiso 1 1 calc R . . H45F H 0.1456 0.8815 0.4696 0.266 Uiso 1 1 calc R . . C46B C 0.112(3) 0.8630(7) 0.656(2) 0.251(11) Uiso 1 1 d D . . H46E H 0.0347 0.8777 0.6763 0.301 Uiso 1 1 calc R . . H46F H 0.0710 0.8426 0.6251 0.301 Uiso 1 1 calc R . . C47B C 0.205(3) 0.8576(6) 0.774(3) 0.300(14) Uiso 1 1 d D . . H47E H 0.1491 0.8522 0.8493 0.360 Uiso 1 1 calc R . . H47F H 0.2709 0.8399 0.7590 0.360 Uiso 1 1 calc R . . O11A O 0.914(5) 0.9112(12) 0.311(5) 0.29(2) Uiso 0.45(3) 1 d P . . O22B O 0.417(2) 0.9445(6) 0.953(2) 0.160(11) Uiso 0.48(2) 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 0.080(4) 0.083(5) 0.064(4) -0.009(4) -0.008(3) 0.035(4) O2A 0.070(4) 0.069(4) 0.071(4) -0.013(3) -0.014(3) 0.024(3) O3A 0.055(3) 0.062(4) 0.049(3) -0.009(3) -0.009(3) 0.007(3) O4A 0.057(4) 0.070(4) 0.051(4) -0.010(3) -0.012(3) 0.019(3) C1A 0.052(5) 0.046(6) 0.055(5) -0.004(4) 0.000(4) 0.005(4) C2A 0.051(5) 0.069(6) 0.044(5) -0.012(5) -0.001(4) 0.016(5) C3A 0.043(5) 0.075(7) 0.033(4) 0.009(5) -0.002(4) -0.008(5) C4A 0.066(6) 0.059(7) 0.063(6) 0.018(5) -0.016(5) -0.008(6) C5A 0.112(10) 0.085(9) 0.071(7) 0.024(6) -0.031(7) -0.040(8) C6A 0.109(11) 0.119(12) 0.082(8) 0.030(8) -0.020(8) -0.064(9) C7A 0.067(8) 0.149(12) 0.069(7) 0.034(8) -0.007(6) -0.055(9) C8A 0.051(6) 0.139(11) 0.063(6) 0.017(7) 0.000(5) 0.004(7) C9A 0.046(5) 0.055(6) 0.058(6) 0.010(4) -0.002(5) 0.001(4) C10A 0.060(6) 0.093(8) 0.047(5) 0.006(5) -0.002(5) -0.001(6) C11A 0.053(7) 0.101(9) 0.073(7) -0.004(6) 0.003(5) -0.019(6) C12A 0.057(7) 0.087(8) 0.101(9) -0.012(6) -0.009(7) 0.002(6) C13A 0.071(7) 0.100(8) 0.063(6) -0.009(6) -0.016(6) 0.002(6) C14A 0.067(7) 0.095(8) 0.053(6) -0.001(5) -0.001(5) 0.019(6) C15A 0.042(5) 0.068(6) 0.043(5) -0.007(5) 0.002(4) 0.011(5) C16A 0.050(6) 0.050(6) 0.070(6) -0.010(5) -0.001(5) 0.015(5) C17A 0.056(6) 0.066(7) 0.090(8) 0.032(6) 0.012(6) 0.023(6) C18A 0.081(8) 0.086(9) 0.089(8) 0.032(7) 0.015(7) 0.026(6) C19A 0.087(10) 0.197(17) 0.138(12) 0.103(12) 0.057(9) 0.067(11) C20A 0.066(9) 0.162(16) 0.21(2) 0.125(15) 0.022(11) 0.033(10) C21A 0.075(10) 0.141(14) 0.188(15) 0.092(13) -0.003(11) 0.003(9) C22A 0.063(7) 0.070(8) 0.152(11) 0.043(8) -0.008(8) -0.005(6) C23A 0.052(5) 0.057(6) 0.047(5) 0.004(4) 0.003(4) 0.016(5) C24A 0.051(6) 0.087(8) 0.120(9) 0.003(7) -0.012(6) 0.023(6) C25A 0.075(8) 0.111(11) 0.099(8) -0.016(7) -0.014(7) 0.035(8) C26A 0.057(6) 0.101(9) 0.069(6) 0.022(6) -0.003(5) -0.005(7) C27A 0.069(7) 0.079(8) 0.068(6) 0.008(6) -0.006(5) -0.001(6) C28A 0.053(6) 0.067(7) 0.070(6) -0.002(5) 0.001(5) 0.007(5) C29A 0.048(5) 0.050(6) 0.044(5) -0.006(4) -0.010(4) 0.010(5) C30A 0.059(6) 0.078(7) 0.055(6) -0.018(5) 0.002(5) -0.004(5) C31A 0.079(7) 0.087(8) 0.051(6) -0.014(5) 0.009(5) 0.009(6) C32A 0.076(7) 0.059(7) 0.093(8) -0.008(6) 0.003(6) -0.004(6) C33A 0.066(6) 0.062(7) 0.072(6) -0.004(5) -0.004(5) -0.012(5) C34A 0.050(5) 0.047(6) 0.070(6) 0.011(5) -0.002(5) 0.002(5) C35A 0.171(15) 0.087(11) 0.092(9) 0.015(8) -0.003(9) 0.000(11) C36A 0.173(17) 0.129(15) 0.136(13) -0.001(11) -0.001(12) 0.027(13) C37A 0.37(4) 0.15(2) 0.154(17) -0.075(15) -0.04(2) 0.01(2) C38A 0.144(14) 0.27(3) 0.128(13) 0.011(15) 0.032(11) 0.078(18) C39A 0.145(15) 0.130(15) 0.199(19) 0.065(13) -0.047(15) -0.036(14) C40A 0.193(19) 0.098(13) 0.130(12) -0.006(9) -0.046(12) 0.013(12) O1B 0.078(4) 0.066(4) 0.069(4) 0.011(3) 0.024(3) 0.017(3) O2B 0.072(4) 0.075(4) 0.054(3) 0.011(3) 0.010(3) 0.021(4) O3B 0.058(4) 0.062(4) 0.054(4) 0.012(3) 0.017(3) 0.017(3) O4B 0.041(3) 0.057(4) 0.055(3) 0.014(3) 0.004(3) 0.009(3) C1B 0.043(5) 0.052(6) 0.051(5) 0.006(5) 0.006(4) -0.002(4) C2B 0.068(6) 0.049(6) 0.058(6) 0.003(5) 0.013(5) 0.006(5) C3B 0.050(5) 0.063(6) 0.054(5) -0.007(5) 0.013(4) 0.009(5) C4B 0.057(6) 0.051(6) 0.097(7) -0.010(5) 0.011(5) 0.003(5) C5B 0.055(6) 0.081(8) 0.093(7) 0.001(6) 0.027(5) -0.004(6) C6B 0.056(6) 0.102(10) 0.099(8) -0.012(7) 0.023(6) 0.011(7) C7B 0.093(9) 0.070(8) 0.099(8) 0.006(6) 0.032(7) 0.032(7) C8B 0.067(7) 0.071(8) 0.109(8) 0.012(6) 0.030(6) 0.014(6) C9B 0.054(6) 0.058(7) 0.085(8) -0.014(6) 0.006(6) 0.013(5) C10B 0.102(9) 0.083(8) 0.091(9) -0.020(7) -0.009(7) 0.051(7) C11B 0.136(12) 0.108(11) 0.109(10) -0.067(9) -0.046(9) 0.059(9) C12B 0.087(10) 0.170(18) 0.200(18) -0.133(16) -0.039(11) 0.039(11) C13B 0.072(9) 0.120(12) 0.25(2) -0.108(14) 0.017(11) -0.021(8) C14B 0.074(8) 0.098(10) 0.130(10) -0.045(8) 0.030(7) -0.026(7) C15B 0.049(5) 0.047(6) 0.062(6) -0.009(5) 0.007(4) -0.005(5) C16B 0.051(5) 0.051(6) 0.042(5) 0.003(4) -0.006(4) 0.012(5) C17B 0.044(6) 0.061(6) 0.053(5) -0.001(5) 0.007(4) 0.001(5) C18B 0.054(6) 0.071(7) 0.060(6) 0.001(5) 0.000(5) -0.006(6) C19B 0.071(7) 0.064(7) 0.053(6) 0.005(5) 0.017(5) -0.001(6) C20B 0.101(9) 0.101(10) 0.054(6) -0.015(6) 0.011(6) -0.033(8) C21B 0.058(7) 0.101(9) 0.087(8) -0.027(7) -0.003(6) -0.015(7) C22B 0.048(6) 0.101(9) 0.074(6) -0.018(6) -0.001(5) 0.012(6) C23B 0.055(6) 0.039(5) 0.068(6) 0.010(5) 0.007(5) -0.003(4) C24B 0.060(6) 0.078(7) 0.048(6) 0.006(5) 0.003(5) -0.005(5) C25B 0.070(7) 0.102(8) 0.070(6) 0.014(6) 0.023(6) -0.010(6) C26B 0.070(7) 0.095(9) 0.089(8) 0.015(7) 0.035(7) -0.005(6) C27B 0.060(7) 0.109(9) 0.082(8) -0.004(6) 0.005(6) -0.011(6) C28B 0.059(6) 0.081(7) 0.057(5) 0.001(5) 0.005(5) 0.001(5) C29B 0.038(5) 0.053(6) 0.060(6) 0.004(5) 0.016(5) 0.008(5) C30B 0.055(6) 0.054(6) 0.055(6) -0.003(5) -0.004(5) 0.004(5) C31B 0.064(6) 0.074(7) 0.065(6) 0.013(5) 0.008(5) -0.019(5) C32B 0.060(6) 0.067(8) 0.072(6) 0.020(5) 0.002(5) -0.002(5) C33B 0.062(6) 0.091(8) 0.050(6) 0.013(5) 0.002(5) 0.014(6) C34B 0.047(5) 0.074(6) 0.047(5) 0.006(5) 0.003(4) 0.003(5) C35B 0.175(15) 0.069(9) 0.097(9) 0.009(7) 0.025(9) -0.016(10) C36B 0.21(2) 0.157(18) 0.113(12) -0.004(11) 0.001(13) -0.039(17) C37B 0.22(2) 0.093(12) 0.165(16) -0.039(11) 0.044(15) -0.023(13) C38B 0.167(16) 0.22(3) 0.099(11) 0.028(14) 0.004(11) -0.039(19) C39B 0.22(2) 0.112(14) 0.147(16) 0.023(11) 0.054(15) 0.010(16) C40B 0.137(13) 0.086(13) 0.137(12) 0.023(9) 0.028(10) -0.012(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 C2A 1.447(10) . ? O1A H1OA 0.8200 . ? O2A C16A 1.423(10) . ? O2A H2OA 0.8200 . ? O3A C1A 1.434(9) . ? O3A C29A 1.449(9) . ? O4A C15A 1.413(9) . ? O4A C29A 1.422(9) . ? C1A C15A 1.537(11) . ? C1A C2A 1.580(11) . ? C1A H1A 0.9800 . ? C2A C3A 1.510(11) . ? C2A C9A 1.566(9) . ? C3A C4A 1.3900 . ? C3A C8A 1.3900 . ? C4A C5A 1.3900 . ? C4A H4A 0.9300 . ? C5A C6A 1.3900 . ? C5A H5A 0.9300 . ? C6A C7A 1.3900 . ? C6A H6A 0.9300 . ? C7A C8A 1.3900 . ? C7A H7A 0.9300 . ? C8A H8A 0.9300 . ? C9A C10A 1.3900 . ? C9A C14A 1.3900 . ? C10A C11A 1.3900 . ? C10A H10A 0.9300 . ? C11A C12A 1.3900 . ? C11A H11A 0.9300 . ? C12A C13A 1.3900 . ? C12A H12A 0.9300 . ? C13A C14A 1.3900 . ? C13A H13A 0.9300 . ? C14A H14A 0.9300 . ? C15A C16A 1.541(11) . ? C15A H15A 0.9800 . ? C16A C17A 1.549(11) . ? C16A C23A 1.553(9) . ? C17A C18A 1.3900 . ? C17A C22A 1.3900 . ? C18A C19A 1.3900 . ? C18A H18A 0.9300 . ? C19A C20A 1.3900 . ? C19A H19A 0.9300 . ? C20A C21A 1.3900 . ? C20A H20A 0.9300 . ? C21A C22A 1.3900 . ? C21A H21A 0.9300 . ? C22A H22A 0.9429 . ? C23A C24A 1.3900 . ? C23A C28A 1.3900 . ? C24A C25A 1.3900 . ? C24A H24A 0.9300 . ? C25A C26A 1.3900 . ? C25A H25A 0.9300 . ? C26A C27A 1.3900 . ? C26A H26A 0.9300 . ? C27A C28A 1.3900 . ? C27A H27A 0.9300 . ? C28A H28A 0.9300 . ? C29A C34A 1.511(11) . ? C29A C30A 1.517(11) . ? C30A C31A 1.549(12) . ? C30A H30C 0.9700 . ? C30A H30D 0.9700 . ? C31A C32A 1.483(13) . ? C31A H31C 0.9700 . ? C31A H31D 0.9700 . ? C32A C33A 1.523(12) . ? C32A H32C 0.9700 . ? C32A H32D 0.9700 . ? C33A C34A 1.521(11) . ? C33A H33C 0.9700 . ? C33A H33D 0.9700 . ? C34A H34C 0.9700 . ? C34A H34D 0.9700 . ? O5A C43A 1.415(10) . ? O5A C41A 1.438(9) . ? O5A O11A 1.96(5) . ? O6A C42A 1.228(8) . ? N1A C42A 1.301(9) . ? N1A C47A 1.448(10) . ? N1A C43A 1.473(10) . ? C35A C36A 1.3900 . ? C35A C40A 1.3900 . ? C35A C41A 1.472(9) . ? C36A C37A 1.3900 . ? C36A H36A 0.9300 . ? C37A C38A 1.3900 . ? C37A H37A 0.9300 . ? C38A C39A 1.3900 . ? C38A H38A 0.9300 . ? C39A C40A 1.3900 . ? C39A H39A 0.9300 . ? C40A H40A 0.9300 . ? C41A C42A 1.492(9) . ? C41A H41A 0.9800 . ? C43A C44A 1.477(10) . ? C43A H43A 0.9800 . ? C44A C45A 1.512(10) . ? C44A H44C 0.9700 . ? C44A H44D 0.9700 . ? C45A C46A 1.524(10) . ? C45A H45C 0.9700 . ? C45A H45D 0.9700 . ? C46A C47A 1.493(10) . ? C46A H46C 0.9700 . ? C46A H46D 0.9700 . ? C47A H47C 0.9700 . ? C47A H47D 0.9700 . ? O1B C2B 1.466(10) . ? O1B H1OB 0.8200 . ? O2B C16B 1.414(9) . ? O2B H2OB 0.8200 . ? O3B C1B 1.399(9) . ? O3B C29B 1.429(9) . ? O4B C15B 1.410(9) . ? O4B C29B 1.444(9) . ? C1B C15B 1.537(11) . ? C1B C2B 1.555(12) . ? C1B H1B 0.9800 . ? C2B C9B 1.520(10) . ? C2B C3B 1.556(10) . ? C3B C4B 1.3900 . ? C3B C8B 1.3900 . ? C4B C5B 1.3900 . ? C4B H4B 0.9300 . ? C5B C6B 1.3900 . ? C5B H5B 0.9300 . ? C6B C7B 1.3900 . ? C6B H6B 0.9300 . ? C7B C8B 1.3900 . ? C7B H7B 0.9300 . ? C8B H8B 0.9300 . ? C9B C10B 1.3900 . ? C9B C14B 1.3900 . ? C10B C11B 1.3900 . ? C10B H10B 0.9300 . ? C11B C12B 1.3900 . ? C11B H11B 0.9300 . ? C12B C13B 1.3900 . ? C12B H12B 0.9300 . ? C13B C14B 1.3900 . ? C13B H13B 0.9300 . ? C14B H14B 0.9300 . ? C15B C16B 1.551(11) . ? C15B H15B 0.9800 . ? C16B C17B 1.564(9) . ? C16B C23B 1.564(9) . ? C17B C18B 1.3900 . ? C17B C22B 1.3900 . ? C18B C19B 1.3900 . ? C18B H18B 0.9300 . ? C19B C20B 1.3900 . ? C19B H19B 0.9300 . ? C20B C21B 1.3900 . ? C20B H20B 0.9300 . ? C21B C22B 1.3900 . ? C21B H21B 0.9300 . ? C22B H22B 0.9300 . ? C23B C24B 1.3900 . ? C23B C28B 1.3900 . ? C24B C25B 1.3900 . ? C24B H24B 0.9300 . ? C25B C26B 1.3900 . ? C25B H25B 0.9300 . ? C26B C27B 1.3900 . ? C26B H26B 0.9300 . ? C27B C28B 1.3900 . ? C27B H27B 0.9300 . ? C28B H28B 0.9409 . ? C29B C30B 1.499(11) . ? C29B C34B 1.513(11) . ? C30B C31B 1.499(11) . ? C30B H30E 0.9700 . ? C30B H30F 0.9700 . ? C31B C32B 1.536(12) . ? C31B H31E 0.9700 . ? C31B H31F 0.9700 . ? C32B C33B 1.460(12) . ? C32B H32E 0.9700 . ? C32B H32F 0.9700 . ? C33B C34B 1.520(12) . ? C33B H33E 0.9700 . ? C33B H33F 0.9700 . ? C34B H34E 0.9700 . ? C34B H34F 0.9700 . ? C35B C36B 1.3900 . ? C35B C40B 1.3900 . ? C35B C41B 1.474(9) . ? C36B C37B 1.3900 . ? C36B H36B 0.9300 . ? C37B C38B 1.3900 . ? C37B H37B 0.9300 . ? C38B C39B 1.3900 . ? C38B H38B 0.9300 . ? C39B C40B 1.3900 . ? C39B H39B 0.9300 . ? C40B H40B 0.9300 . ? O5B C43B 1.420(10) . ? O5B C41B 1.426(9) . ? O6B C42B 1.231(9) . ? N1B C42B 1.315(10) . ? N1B C47B 1.439(10) . ? N1B C43B 1.455(10) . ? C41B C42B 1.491(9) . ? C41B H41B 0.9800 . ? C43B C44B 1.472(10) . ? C43B H43B 0.9800 . ? C44B C45B 1.523(10) . ? C44B H44E 0.9700 . ? C44B H44F 0.9700 . ? C45B C46B 1.521(10) . ? C45B H45E 0.9700 . ? C45B H45F 0.9700 . ? C46B C47B 1.487(10) . ? C46B H46E 0.9700 . ? C46B H46F 0.9700 . ? C47B H47E 0.9700 . ? C47B H47F 0.9700 . ? 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 C2A O1A H1OA 109.5 . . ? C16A O2A H2OA 109.5 . . ? C1A O3A C29A 109.3(6) . . ? C15A O4A C29A 109.2(5) . . ? O3A C1A C15A 104.7(6) . . ? O3A C1A C2A 108.2(6) . . ? C15A C1A C2A 117.0(7) . . ? O3A C1A H1A 108.9 . . ? C15A C1A H1A 109.0 . . ? C2A C1A H1A 108.9 . . ? O1A C2A C3A 110.9(7) . . ? O1A C2A C9A 104.2(6) . . ? C3A C2A C9A 109.9(6) . . ? O1A C2A C1A 107.5(6) . . ? C3A C2A C1A 112.3(6) . . ? C9A C2A C1A 111.7(6) . . ? C4A C3A C8A 120.0 . . ? C4A C3A C2A 119.9(6) . . ? C8A C3A C2A 120.1(6) . . ? C3A C4A C5A 120.0 . . ? C3A C4A H4A 120.0 . . ? C5A C4A H4A 120.0 . . ? C6A C5A C4A 120.0 . . ? C6A C5A H5A 120.0 . . ? C4A C5A H5A 120.0 . . ? C5A C6A C7A 120.0 . . ? C5A C6A H6A 120.0 . . ? C7A C6A H6A 120.0 . . ? C8A C7A C6A 120.0 . . ? C8A C7A H7A 120.0 . . ? C6A C7A H7A 120.0 . . ? C7A C8A C3A 120.0 . . ? C7A C8A H8A 120.0 . . ? C3A C8A H8A 120.0 . . ? C10A C9A C14A 120.0 . . ? C10A C9A C2A 124.1(5) . . ? C14A C9A C2A 115.8(5) . . ? C11A C10A C9A 120.0 . . ? C11A C10A H10A 120.0 . . ? C9A C10A H10A 120.0 . . ? C12A C11A C10A 120.0 . . ? C12A C11A H11A 120.0 . . ? C10A C11A H11A 120.0 . . ? C11A C12A C13A 120.0 . . ? C11A C12A H12A 120.0 . . ? C13A C12A H12A 120.0 . . ? C14A C13A C12A 120.0 . . ? C14A C13A H13A 120.0 . . ? C12A C13A H13A 120.0 . . ? C13A C14A C9A 120.0 . . ? C13A C14A H14A 120.0 . . ? C9A C14A H14A 120.0 . . ? O4A C15A C1A 103.3(6) . . ? O4A C15A C16A 107.3(6) . . ? C1A C15A C16A 116.8(7) . . ? O4A C15A H15A 109.7 . . ? C1A C15A H15A 109.7 . . ? C16A C15A H15A 109.7 . . ? O2A C16A C15A 102.8(6) . . ? O2A C16A C17A 110.8(7) . . ? C15A C16A C17A 112.8(6) . . ? O2A C16A C23A 108.1(6) . . ? C15A C16A C23A 112.4(6) . . ? C17A C16A C23A 109.7(6) . . ? C18A C17A C22A 120.0 . . ? C18A C17A C16A 119.9(7) . . ? C22A C17A C16A 120.0(7) . . ? C17A C18A C19A 120.0 . . ? C17A C18A H18A 120.0 . . ? C19A C18A H18A 120.0 . . ? C20A C19A C18A 120.0 . . ? C20A C19A H19A 120.0 . . ? C18A C19A H19A 120.0 . . ? C19A C20A C21A 120.0 . . ? C19A C20A H20A 120.0 . . ? C21A C20A H20A 120.0 . . ? C22A C21A C20A 120.0 . . ? C22A C21A H21A 120.0 . . ? C20A C21A H21A 120.0 . . ? C21A C22A C17A 120.0 . . ? C21A C22A H22A 119.9 . . ? C17A C22A H22A 120.0 . . ? C24A C23A C28A 120.0 . . ? C24A C23A C16A 116.7(5) . . ? C28A C23A C16A 123.3(5) . . ? C25A C24A C23A 120.0 . . ? C25A C24A H24A 120.0 . . ? C23A C24A H24A 120.0 . . ? C24A C25A C26A 120.0 . . ? C24A C25A H25A 120.0 . . ? C26A C25A H25A 120.0 . . ? C27A C26A C25A 120.0 . . ? C27A C26A H26A 120.0 . . ? C25A C26A H26A 120.0 . . ? C26A C27A C28A 120.0 . . ? C26A C27A H27A 120.0 . . ? C28A C27A H27A 120.0 . . ? C27A C28A C23A 120.0 . . ? C27A C28A H28A 120.0 . . ? C23A C28A H28A 120.0 . . ? O4A C29A O3A 105.5(6) . . ? O4A C29A C34A 110.5(7) . . ? O3A C29A C34A 111.0(6) . . ? O4A C29A C30A 109.0(6) . . ? O3A C29A C30A 107.8(6) . . ? C34A C29A C30A 112.7(7) . . ? C29A C30A C31A 110.9(7) . . ? C29A C30A H30C 109.5 . . ? C31A C30A H30C 109.4 . . ? C29A C30A H30D 109.4 . . ? C31A C30A H30D 109.5 . . ? H30C C30A H30D 108.0 . . ? C32A C31A C30A 111.2(8) . . ? C32A C31A H31C 109.4 . . ? C30A C31A H31C 109.4 . . ? C32A C31A H31D 109.4 . . ? C30A C31A H31D 109.4 . . ? H31C C31A H31D 108.0 . . ? C31A C32A C33A 110.7(8) . . ? C31A C32A H32C 109.5 . . ? C33A C32A H32C 109.5 . . ? C31A C32A H32D 109.5 . . ? C33A C32A H32D 109.5 . . ? H32C C32A H32D 108.1 . . ? C34A C33A C32A 112.7(7) . . ? C34A C33A H33C 109.0 . . ? C32A C33A H33C 109.1 . . ? C34A C33A H33D 109.1 . . ? C32A C33A H33D 109.0 . . ? H33C C33A H33D 107.8 . . ? C29A C34A C33A 110.3(7) . . ? C29A C34A H34C 109.6 . . ? C33A C34A H34C 109.6 . . ? C29A C34A H34D 109.6 . . ? C33A C34A H34D 109.6 . . ? H34C C34A H34D 108.1 . . ? C43A O5A C41A 107.3(15) . . ? C43A O5A O11A 137.2(19) . . ? C41A O5A O11A 39.5(15) . . ? C42A N1A C47A 124.9(15) . . ? C42A N1A C43A 113.9(14) . . ? C47A N1A C43A 119.8(15) . . ? C36A C35A C40A 120.0 . . ? C36A C35A C41A 116.7(14) . . ? C40A C35A C41A 123.3(13) . . ? C37A C36A C35A 120.0 . . ? C37A C36A H36A 120.0 . . ? C35A C36A H36A 120.0 . . ? C36A C37A C38A 120.0 . . ? C36A C37A H37A 120.0 . . ? C38A C37A H37A 120.0 . . ? C37A C38A C39A 120.0 . . ? C37A C38A H38A 120.0 . . ? C39A C38A H38A 120.0 . . ? C40A C39A C38A 120.0 . . ? C40A C39A H39A 120.0 . . ? C38A C39A H39A 120.0 . . ? C39A C40A C35A 120.0 . . ? C39A C40A H40A 120.0 . . ? C35A C40A H40A 120.0 . . ? O5A C41A C35A 110.3(12) . . ? O5A C41A C42A 105.6(12) . . ? C35A C41A C42A 113.4(12) . . ? O5A C41A H41A 109.1 . . ? C35A C41A H41A 109.2 . . ? C42A C41A H41A 109.2 . . ? O6A C42A N1A 128.8(13) . . ? O6A C42A C41A 125.6(12) . . ? N1A C42A C41A 105.4(12) . . ? O5A C43A N1A 101.8(15) . . ? O5A C43A C44A 110.8(16) . . ? N1A C43A C44A 110.6(16) . . ? O5A C43A H43A 111.1 . . ? N1A C43A H43A 111.0 . . ? C44A C43A H43A 111.2 . . ? C43A C44A C45A 105.2(17) . . ? C43A C44A H44C 110.9 . . ? C45A C44A H44C 110.8 . . ? C43A C44A H44D 110.6 . . ? C45A C44A H44D 110.6 . . ? H44C C44A H44D 108.8 . . ? C44A C45A C46A 111.1(17) . . ? C44A C45A H45C 109.5 . . ? C46A C45A H45C 109.2 . . ? C44A C45A H45D 109.5 . . ? C46A C45A H45D 109.5 . . ? H45C C45A H45D 108.1 . . ? C47A C46A C45A 111.6(17) . . ? C47A C46A H46C 109.3 . . ? C45A C46A H46C 109.0 . . ? C47A C46A H46D 109.3 . . ? C45A C46A H46D 109.6 . . ? H46C C46A H46D 108.0 . . ? N1A C47A C46A 106.6(15) . . ? N1A C47A H47C 110.4 . . ? C46A C47A H47C 110.5 . . ? N1A C47A H47D 110.4 . . ? C46A C47A H47D 110.4 . . ? H47C C47A H47D 108.6 . . ? C2B O1B H1OB 109.5 . . ? C16B O2B H2OB 109.5 . . ? C1B O3B C29B 110.8(6) . . ? C15B O4B C29B 112.2(6) . . ? O3B C1B C15B 104.7(6) . . ? O3B C1B C2B 108.1(6) . . ? C15B C1B C2B 116.1(7) . . ? O3B C1B H1B 109.3 . . ? C15B C1B H1B 109.3 . . ? C2B C1B H1B 109.3 . . ? O1B C2B C9B 110.0(7) . . ? O1B C2B C3B 107.7(6) . . ? C9B C2B C3B 109.8(6) . . ? O1B C2B C1B 102.0(6) . . ? C9B C2B C1B 114.1(7) . . ? C3B C2B C1B 112.9(7) . . ? C4B C3B C8B 120.0 . . ? C4B C3B C2B 123.7(5) . . ? C8B C3B C2B 116.3(5) . . ? C5B C4B C3B 120.0 . . ? C5B C4B H4B 120.0 . . ? C3B C4B H4B 120.0 . . ? C6B C5B C4B 120.0 . . ? C6B C5B H5B 120.0 . . ? C4B C5B H5B 120.0 . . ? C7B C6B C5B 120.0 . . ? C7B C6B H6B 120.0 . . ? C5B C6B H6B 120.0 . . ? C6B C7B C8B 120.0 . . ? C6B C7B H7B 120.0 . . ? C8B C7B H7B 120.0 . . ? C7B C8B C3B 120.0 . . ? C7B C8B H8B 120.0 . . ? C3B C8B H8B 120.0 . . ? C10B C9B C14B 120.0 . . ? C10B C9B C2B 118.8(7) . . ? C14B C9B C2B 121.2(7) . . ? C11B C10B C9B 120.0 . . ? C11B C10B H10B 120.0 . . ? C9B C10B H10B 120.0 . . ? C10B C11B C12B 120.0 . . ? C10B C11B H11B 120.0 . . ? C12B C11B H11B 120.0 . . ? C13B C12B C11B 120.0 . . ? C13B C12B H12B 120.0 . . ? C11B C12B H12B 120.0 . . ? C12B C13B C14B 120.0 . . ? C12B C13B H13B 120.0 . . ? C14B C13B H13B 120.0 . . ? C13B C14B C9B 120.0 . . ? C13B C14B H14B 120.0 . . ? C9B C14B H14B 120.0 . . ? O4B C15B C1B 103.7(6) . . ? O4B C15B C16B 111.3(6) . . ? C1B C15B C16B 117.3(6) . . ? O4B C15B H15B 108.0 . . ? C1B C15B H15B 108.1 . . ? C16B C15B H15B 108.0 . . ? O2B C16B C15B 109.9(6) . . ? O2B C16B C17B 109.4(5) . . ? C15B C16B C17B 110.6(6) . . ? O2B C16B C23B 105.7(6) . . ? C15B C16B C23B 113.3(6) . . ? C17B C16B C23B 107.7(6) . . ? C18B C17B C22B 120.0 . . ? C18B C17B C16B 120.4(5) . . ? C22B C17B C16B 119.6(5) . . ? C17B C18B C19B 120.0 . . ? C17B C18B H18B 120.0 . . ? C19B C18B H18B 120.0 . . ? C20B C19B C18B 120.0 . . ? C20B C19B H19B 120.0 . . ? C18B C19B H19B 120.0 . . ? C19B C20B C21B 120.0 . . ? C19B C20B H20B 120.0 . . ? C21B C20B H20B 120.0 . . ? C22B C21B C20B 120.0 . . ? C22B C21B H21B 120.0 . . ? C20B C21B H21B 120.0 . . ? C21B C22B C17B 120.0 . . ? C21B C22B H22B 120.0 . . ? C17B C22B H22B 120.0 . . ? C24B C23B C28B 120.0 . . ? C24B C23B C16B 116.5(5) . . ? C28B C23B C16B 123.4(5) . . ? C25B C24B C23B 120.0 . . ? C25B C24B H24B 120.0 . . ? C23B C24B H24B 120.0 . . ? C24B C25B C26B 120.0 . . ? C24B C25B H25B 120.0 . . ? C26B C25B H25B 120.0 . . ? C27B C26B C25B 120.0 . . ? C27B C26B H26B 120.0 . . ? C25B C26B H26B 120.0 . . ? C26B C27B C28B 120.0 . . ? C26B C27B H27B 120.0 . . ? C28B C27B H27B 120.0 . . ? C27B C28B C23B 120.0 . . ? C27B C28B H28B 120.3 . . ? C23B C28B H28B 119.7 . . ? O3B C29B O4B 103.7(6) . . ? O3B C29B C30B 110.7(7) . . ? O4B C29B C30B 110.9(7) . . ? O3B C29B C34B 108.3(7) . . ? O4B C29B C34B 109.7(6) . . ? C30B C29B C34B 113.0(7) . . ? C31B C30B C29B 112.0(7) . . ? C31B C30B H30E 109.2 . . ? C29B C30B H30E 109.2 . . ? C31B C30B H30F 109.2 . . ? C29B C30B H30F 109.3 . . ? H30E C30B H30F 107.9 . . ? C30B C31B C32B 110.2(7) . . ? C30B C31B H31E 109.7 . . ? C32B C31B H31E 109.6 . . ? C30B C31B H31F 109.5 . . ? C32B C31B H31F 109.6 . . ? H31E C31B H31F 108.1 . . ? C33B C32B C31B 109.6(7) . . ? C33B C32B H32E 109.7 . . ? C31B C32B H32E 109.8 . . ? C33B C32B H32F 109.8 . . ? C31B C32B H32F 109.8 . . ? H32E C32B H32F 108.2 . . ? C32B C33B C34B 113.7(8) . . ? C32B C33B H33E 108.8 . . ? C34B C33B H33E 108.8 . . ? C32B C33B H33F 108.9 . . ? C34B C33B H33F 108.8 . . ? H33E C33B H33F 107.7 . . ? C29B C34B C33B 109.7(7) . . ? C29B C34B H34E 109.7 . . ? C33B C34B H34E 109.8 . . ? C29B C34B H34F 109.7 . . ? C33B C34B H34F 109.7 . . ? H34E C34B H34F 108.2 . . ? C36B C35B C40B 120.0 . . ? C36B C35B C41B 116.0(13) . . ? C40B C35B C41B 124.0(13) . . ? C35B C36B C37B 120.0 . . ? C35B C36B H36B 120.0 . . ? C37B C36B H36B 120.0 . . ? C36B C37B C38B 120.0 . . ? C36B C37B H37B 120.0 . . ? C38B C37B H37B 120.0 . . ? C39B C38B C37B 120.0 . . ? C39B C38B H38B 120.0 . . ? C37B C38B H38B 120.0 . . ? C38B C39B C40B 120.0 . . ? C38B C39B H39B 120.0 . . ? C40B C39B H39B 120.0 . . ? C39B C40B C35B 120.0 . . ? C39B C40B H40B 120.0 . . ? C35B C40B H40B 120.0 . . ? C43B O5B C41B 111.0(16) . . ? C42B N1B C47B 108.0(19) . . ? C42B N1B C43B 121.4(18) . . ? C47B N1B C43B 114(2) . . ? O5B C41B C35B 110.4(12) . . ? O5B C41B C42B 104.1(13) . . ? C35B C41B C42B 113.0(12) . . ? O5B C41B H41B 109.8 . . ? C35B C41B H41B 109.7 . . ? C42B C41B H41B 109.7 . . ? O6B C42B N1B 137.1(17) . . ? O6B C42B C41B 125.5(14) . . ? N1B C42B C41B 96.6(14) . . ? O5B C43B N1B 87.7(17) . . ? O5B C43B C44B 105.0(17) . . ? N1B C43B C44B 94.5(19) . . ? O5B C43B H43B 120.9 . . ? N1B C43B H43B 120.9 . . ? C44B C43B H43B 120.7 . . ? C43B C44B C45B 97.9(17) . . ? C43B C44B H44E 112.0 . . ? C45B C44B H44E 112.0 . . ? C43B C44B H44F 112.4 . . ? C45B C44B H44F 112.3 . . ? H44E C44B H44F 109.9 . . ? C44B C45B C46B 106(2) . . ? C44B C45B H45E 110.4 . . ? C46B C45B H45E 110.9 . . ? C44B C45B H45F 110.6 . . ? C46B C45B H45F 110.4 . . ? H45E C45B H45F 108.6 . . ? C47B C46B C45B 108(2) . . ? C47B C46B H46E 110.4 . . ? C45B C46B H46E 110.7 . . ? C47B C46B H46F 110.1 . . ? C45B C46B H46F 109.6 . . ? H46E C46B H46F 108.5 . . ? N1B C47B C46B 106(2) . . ? N1B C47B H47E 110.5 . . ? C46B C47B H47E 110.4 . . ? N1B C47B H47F 110.4 . . ? C46B C47B H47F 110.7 . . ? H47E C47B H47F 108.7 . . ? 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 C29A O3A C1A C15A -7.4(8) . . . . ? C29A O3A C1A C2A -132.8(7) . . . . ? O3A C1A C2A O1A -179.6(6) . . . . ? C15A C1A C2A O1A 62.6(9) . . . . ? O3A C1A C2A C3A 58.1(8) . . . . ? C15A C1A C2A C3A -59.7(9) . . . . ? O3A C1A C2A C9A -65.9(8) . . . . ? C15A C1A C2A C9A 176.4(7) . . . . ? O1A C2A C3A C4A 160.3(4) . . . . ? C9A C2A C3A C4A 45.7(7) . . . . ? C1A C2A C3A C4A -79.3(7) . . . . ? O1A C2A C3A C8A -22.1(7) . . . . ? C9A C2A C3A C8A -136.8(5) . . . . ? C1A C2A C3A C8A 98.3(6) . . . . ? C8A C3A C4A C5A 0.0 . . . . ? C2A C3A C4A C5A 177.6(5) . . . . ? C3A C4A C5A C6A 0.0 . . . . ? C4A C5A C6A C7A 0.0 . . . . ? C5A C6A C7A C8A 0.0 . . . . ? C6A C7A C8A C3A 0.0 . . . . ? C4A C3A C8A C7A 0.0 . . . . ? C2A C3A C8A C7A -177.6(5) . . . . ? O1A C2A C9A C10A 119.1(6) . . . . ? C3A C2A C9A C10A -122.0(6) . . . . ? C1A C2A C9A C10A 3.3(9) . . . . ? O1A C2A C9A C14A -58.0(7) . . . . ? C3A C2A C9A C14A 60.9(7) . . . . ? C1A C2A C9A C14A -173.8(5) . . . . ? C14A C9A C10A C11A 0.0 . . . . ? C2A C9A C10A C11A -177.0(7) . . . . ? C9A C10A C11A C12A 0.0 . . . . ? C10A C11A C12A C13A 0.0 . . . . ? C11A C12A C13A C14A 0.0 . . . . ? C12A C13A C14A C9A 0.0 . . . . ? C10A C9A C14A C13A 0.0 . . . . ? C2A C9A C14A C13A 177.2(6) . . . . ? C29A O4A C15A C1A -29.3(8) . . . . ? C29A O4A C15A C16A -153.3(6) . . . . ? O3A C1A C15A O4A 22.0(8) . . . . ? C2A C1A C15A O4A 141.7(7) . . . . ? O3A C1A C15A C16A 139.5(7) . . . . ? C2A C1A C15A C16A -100.8(9) . . . . ? O4A C15A C16A O2A 176.0(6) . . . . ? C1A C15A C16A O2A 60.7(9) . . . . ? O4A C15A C16A C17A 56.6(9) . . . . ? C1A C15A C16A C17A -58.7(9) . . . . ? O4A C15A C16A C23A -68.1(8) . . . . ? C1A C15A C16A C23A 176.6(7) . . . . ? O2A C16A C17A C18A 172.4(5) . . . . ? C15A C16A C17A C18A -72.9(7) . . . . ? C23A C16A C17A C18A 53.2(7) . . . . ? O2A C16A C17A C22A -10.5(8) . . . . ? C15A C16A C17A C22A 104.2(6) . . . . ? C23A C16A C17A C22A -129.7(5) . . . . ? C22A C17A C18A C19A 0.0 . . . . ? C16A C17A C18A C19A 177.1(6) . . . . ? C17A C18A C19A C20A 0.0 . . . . ? C18A C19A C20A C21A 0.0 . . . . ? C19A C20A C21A C22A 0.0 . . . . ? C20A C21A C22A C17A 0.0 . . . . ? C18A C17A C22A C21A 0.0 . . . . ? C16A C17A C22A C21A -177.1(6) . . . . ? O2A C16A C23A C24A -55.9(7) . . . . ? C15A C16A C23A C24A -168.6(5) . . . . ? C17A C16A C23A C24A 65.0(7) . . . . ? O2A C16A C23A C28A 121.1(6) . . . . ? C15A C16A C23A C28A 8.4(9) . . . . ? C17A C16A C23A C28A -118.0(6) . . . . ? C28A C23A C24A C25A 0.0 . . . . ? C16A C23A C24A C25A 177.1(6) . . . . ? C23A C24A C25A C26A 0.0 . . . . ? C24A C25A C26A C27A 0.0 . . . . ? C25A C26A C27A C28A 0.0 . . . . ? C26A C27A C28A C23A 0.0 . . . . ? C24A C23A C28A C27A 0.0 . . . . ? C16A C23A C28A C27A -176.9(6) . . . . ? C15A O4A C29A O3A 25.3(8) . . . . ? C15A O4A C29A C34A -94.8(7) . . . . ? C15A O4A C29A C30A 140.8(7) . . . . ? C1A O3A C29A O4A -9.9(8) . . . . ? C1A O3A C29A C34A 109.9(7) . . . . ? C1A O3A C29A C30A -126.3(7) . . . . ? O4A C29A C30A C31A 69.2(9) . . . . ? O3A C29A C30A C31A -176.7(7) . . . . ? C34A C29A C30A C31A -53.9(10) . . . . ? C29A C30A C31A C32A 55.3(10) . . . . ? C30A C31A C32A C33A -56.1(11) . . . . ? C31A C32A C33A C34A 56.7(11) . . . . ? O4A C29A C34A C33A -68.9(8) . . . . ? O3A C29A C34A C33A 174.4(7) . . . . ? C30A C29A C34A C33A 53.3(9) . . . . ? C32A C33A C34A C29A -54.3(10) . . . . ? C40A C35A C36A C37A 0.0 . . . . ? C41A C35A C36A C37A -178.7(10) . . . . ? C35A C36A C37A C38A 0.0 . . . . ? C36A C37A C38A C39A 0.0 . . . . ? C37A C38A C39A C40A 0.0 . . . . ? C38A C39A C40A C35A 0.0 . . . . ? C36A C35A C40A C39A 0.0 . . . . ? C41A C35A C40A C39A 178.6(11) . . . . ? C43A O5A C41A C35A 100.3(17) . . . . ? O11A O5A C41A C35A -113(3) . . . . ? C43A O5A C41A C42A -22.6(18) . . . . ? O11A O5A C41A C42A 124(3) . . . . ? C36A C35A C41A O5A 98.8(14) . . . . ? C40A C35A C41A O5A -79.8(14) . . . . ? C36A C35A C41A C42A -143.0(10) . . . . ? C40A C35A C41A C42A 38.4(15) . . . . ? C47A N1A C42A O6A -13(3) . . . . ? C43A N1A C42A O6A -179.2(15) . . . . ? C47A N1A C42A C41A 171.7(15) . . . . ? C43A N1A C42A C41A 5.2(18) . . . . ? O5A C41A C42A O6A -165.2(14) . . . . ? C35A C41A C42A O6A 73.9(19) . . . . ? O5A C41A C42A N1A 10.5(17) . . . . ? C35A C41A C42A N1A -110.4(14) . . . . ? C41A O5A C43A N1A 24.3(19) . . . . ? O11A O5A C43A N1A -7(3) . . . . ? C41A O5A C43A C44A 142.0(15) . . . . ? O11A O5A C43A C44A 111(3) . . . . ? C42A N1A C43A O5A -19(2) . . . . ? C47A N1A C43A O5A 173.8(16) . . . . ? C42A N1A C43A C44A -136.6(16) . . . . ? C47A N1A C43A C44A 56(2) . . . . ? O5A C43A C44A C45A -168.7(15) . . . . ? N1A C43A C44A C45A -57(2) . . . . ? C43A C44A C45A C46A 62(2) . . . . ? C44A C45A C46A C47A -62(2) . . . . ? C42A N1A C47A C46A 144.0(17) . . . . ? C43A N1A C47A C46A -50(2) . . . . ? C45A C46A C47A N1A 51(2) . . . . ? C29B O3B C1B C15B -23.2(8) . . . . ? C29B O3B C1B C2B -147.5(6) . . . . ? O3B C1B C2B O1B 177.6(6) . . . . ? C15B C1B C2B O1B 60.4(8) . . . . ? O3B C1B C2B C9B 59.0(9) . . . . ? C15B C1B C2B C9B -58.1(9) . . . . ? O3B C1B C2B C3B -67.2(8) . . . . ? C15B C1B C2B C3B 175.7(6) . . . . ? O1B C2B C3B C4B 127.0(6) . . . . ? C9B C2B C3B C4B -113.2(6) . . . . ? C1B C2B C3B C4B 15.2(9) . . . . ? O1B C2B C3B C8B -51.9(7) . . . . ? C9B C2B C3B C8B 67.9(7) . . . . ? C1B C2B C3B C8B -163.7(5) . . . . ? C8B C3B C4B C5B 0.0 . . . . ? C2B C3B C4B C5B -178.9(6) . . . . ? C3B C4B C5B C6B 0.0 . . . . ? C4B C5B C6B C7B 0.0 . . . . ? C5B C6B C7B C8B 0.0 . . . . ? C6B C7B C8B C3B 0.0 . . . . ? C4B C3B C8B C7B 0.0 . . . . ? C2B C3B C8B C7B 178.9(6) . . . . ? O1B C2B C9B C10B 171.3(5) . . . . ? C3B C2B C9B C10B 53.0(7) . . . . ? C1B C2B C9B C10B -74.8(8) . . . . ? O1B C2B C9B C14B -10.7(8) . . . . ? C3B C2B C9B C14B -129.0(6) . . . . ? C1B C2B C9B C14B 103.2(7) . . . . ? C14B C9B C10B C11B 0.0 . . . . ? C2B C9B C10B C11B 178.0(6) . . . . ? C9B C10B C11B C12B 0.0 . . . . ? C10B C11B C12B C13B 0.0 . . . . ? C11B C12B C13B C14B 0.0 . . . . ? C12B C13B C14B C9B 0.0 . . . . ? C10B C9B C14B C13B 0.0 . . . . ? C2B C9B C14B C13B -178.0(6) . . . . ? C29B O4B C15B C1B -5.0(8) . . . . ? C29B O4B C15B C16B -132.0(7) . . . . ? O3B C1B C15B O4B 16.7(8) . . . . ? C2B C1B C15B O4B 135.7(7) . . . . ? O3B C1B C15B C16B 139.9(7) . . . . ? C2B C1B C15B C16B -101.1(8) . . . . ? O4B C15B C16B O2B 179.1(6) . . . . ? C1B C15B C16B O2B 59.9(9) . . . . ? O4B C15B C16B C17B 58.2(8) . . . . ? C1B C15B C16B C17B -61.0(9) . . . . ? O4B C15B C16B C23B -62.9(8) . . . . ? C1B C15B C16B C23B 177.9(7) . . . . ? O2B C16B C17B C18B 156.2(5) . . . . ? C15B C16B C17B C18B -82.6(7) . . . . ? C23B C16B C17B C18B 41.8(7) . . . . ? O2B C16B C17B C22B -25.0(7) . . . . ? C15B C16B C17B C22B 96.1(6) . . . . ? C23B C16B C17B C22B -139.5(5) . . . . ? C22B C17B C18B C19B 0.0 . . . . ? C16B C17B C18B C19B 178.8(6) . . . . ? C17B C18B C19B C20B 0.0 . . . . ? C18B C19B C20B C21B 0.0 . . . . ? C19B C20B C21B C22B 0.0 . . . . ? C20B C21B C22B C17B 0.0 . . . . ? C18B C17B C22B C21B 0.0 . . . . ? C16B C17B C22B C21B -178.8(6) . . . . ? O2B C16B C23B C24B -52.4(7) . . . . ? C15B C16B C23B C24B -172.8(5) . . . . ? C17B C16B C23B C24B 64.4(6) . . . . ? O2B C16B C23B C28B 123.4(5) . . . . ? C15B C16B C23B C28B 2.9(8) . . . . ? C17B C16B C23B C28B -119.8(5) . . . . ? C28B C23B C24B C25B 0.0 . . . . ? C16B C23B C24B C25B 175.9(6) . . . . ? C23B C24B C25B C26B 0.0 . . . . ? C24B C25B C26B C27B 0.0 . . . . ? C25B C26B C27B C28B 0.0 . . . . ? C26B C27B C28B C23B 0.0 . . . . ? C24B C23B C28B C27B 0.0 . . . . ? C16B C23B C28B C27B -175.6(6) . . . . ? C1B O3B C29B O4B 20.1(8) . . . . ? C1B O3B C29B C30B -99.0(8) . . . . ? C1B O3B C29B C34B 136.6(7) . . . . ? C15B O4B C29B O3B -8.4(8) . . . . ? C15B O4B C29B C30B 110.5(7) . . . . ? C15B O4B C29B C34B -123.9(7) . . . . ? O3B C29B C30B C31B -68.5(9) . . . . ? O4B C29B C30B C31B 177.0(6) . . . . ? C34B C29B C30B C31B 53.2(9) . . . . ? C29B C30B C31B C32B -55.4(10) . . . . ? C30B C31B C32B C33B 57.6(10) . . . . ? C31B C32B C33B C34B -58.2(10) . . . . ? O3B C29B C34B C33B 72.4(9) . . . . ? O4B C29B C34B C33B -175.0(7) . . . . ? C30B C29B C34B C33B -50.6(9) . . . . ? C32B C33B C34B C29B 54.6(10) . . . . ? C40B C35B C36B C37B 0.0 . . . . ? C41B C35B C36B C37B -177.6(9) . . . . ? C35B C36B C37B C38B 0.0 . . . . ? C36B C37B C38B C39B 0.0 . . . . ? C37B C38B C39B C40B 0.0 . . . . ? C38B C39B C40B C35B 0.0 . . . . ? C36B C35B C40B C39B 0.0 . . . . ? C41B C35B C40B C39B 177.4(10) . . . . ? C43B O5B C41B C35B 90.7(17) . . . . ? C43B O5B C41B C42B -31(2) . . . . ? C36B C35B C41B O5B 98.3(14) . . . . ? C40B C35B C41B O5B -79.3(14) . . . . ? C36B C35B C41B C42B -145.6(10) . . . . ? C40B C35B C41B C42B 36.9(16) . . . . ? C47B N1B C42B O6B -29(4) . . . . ? C43B N1B C42B O6B -163(2) . . . . ? C47B N1B C42B C41B 162(2) . . . . ? C43B N1B C42B C41B 27(2) . . . . ? O5B C41B C42B O6B -168.1(16) . . . . ? C35B C41B C42B O6B 72(2) . . . . ? O5B C41B C42B N1B 2.9(18) . . . . ? C35B C41B C42B N1B -117.0(16) . . . . ? C41B O5B C43B N1B 39.5(18) . . . . ? C41B O5B C43B C44B 133.5(18) . . . . ? C42B N1B C43B O5B -43(2) . . . . ? C47B N1B C43B O5B -176(2) . . . . ? C42B N1B C43B C44B -148(2) . . . . ? C47B N1B C43B C44B 80(2) . . . . ? O5B C43B C44B C45B -169.4(18) . . . . ? N1B C43B C44B C45B -81(2) . . . . ? C43B C44B C45B C46B 79(2) . . . . ? C44B C45B C46B C47B -61(3) . . . . ? C42B N1B C47B C46B 159(2) . . . . ? C43B N1B C47B C46B -63(3) . . . . ? C45B C46B C47B N1B 49(3) . . . . ? _diffrn_measured_fraction_theta_max 0.937 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.937 _refine_diff_density_max 0.441 _refine_diff_density_min -0.341 _refine_diff_density_rms 0.089 # Attachment 'IIa.cif' data_IIa' _database_code_depnum_ccdc_archive 'CCDC 664465' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,1,6,6-tetrahphenyl-2,4-hexadiyne-1,6-diol, 4-Oxa-I-azabicyclo[4.2.0] octan-8-one,7-hydroxy-7-phenyl clathrate ; _chemical_name_common ; 1,1,6,6-tetrahphenyl-2,4-hexadiyne-1,6-diol, 4-Oxa-I- azabicyclo(4.2.0) octan-8-one,7-hydroxy-7-phenyl clathrate ; _chemical_melting_point ? _chemical_formula_moiety 'C30 H22 O2, 2(C12 H13 N O3)' _chemical_formula_sum 'C54 H48 N2 O8' _chemical_formula_weight 852.94 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.2010(3) _cell_length_b 26.6670(12) _cell_length_c 14.1970(8) _cell_angle_alpha 90.00 _cell_angle_beta 105.0120(17) _cell_angle_gamma 90.00 _cell_volume 2267.5(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3269 _cell_measurement_theta_min 1.018 _cell_measurement_theta_max 25.08 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.249 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 900 _exptl_absorpt_coefficient_mu 0.084 _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 3423 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1036 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 25.09 _reflns_number_total 3423 _reflns_number_gt 1355 _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.035(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3423 _refine_ls_number_parameters 292 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2152 _refine_ls_R_factor_gt 0.0948 _refine_ls_wR_factor_ref 0.2653 _refine_ls_wR_factor_gt 0.2364 _refine_ls_goodness_of_fit_ref 1.234 _refine_ls_restrained_S_all 1.234 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 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 1.0730(5) 0.07573(15) 1.0215(2) 0.0984(12) Uani 1 1 d . . . H1 H 1.0557 0.0660 0.9652 0.118 Uiso 1 1 calc R . . C1 C 0.5751(10) 0.0207(2) 1.0073(4) 0.0986(18) Uani 1 1 d . . . C2 C 0.7031(10) 0.0545(3) 1.0189(4) 0.0962(17) Uani 1 1 d . . . C3 C 0.8660(10) 0.0953(2) 1.0332(4) 0.0904(16) Uani 1 1 d . . . C4 C 0.7849(11) 0.1361(2) 0.9602(4) 0.0882(16) Uani 1 1 d . . . C5 C 0.5678(15) 0.1470(3) 0.9281(5) 0.141(3) Uani 1 1 d . . . H5 H 0.4625 0.1268 0.9503 0.169 Uiso 1 1 d R . . C6 C 0.4861(13) 0.1850(4) 0.8619(7) 0.173(3) Uani 1 1 d . . . H6 H 0.3306 0.1937 0.8423 0.208 Uiso 1 1 d R . . C7 C 0.6350(18) 0.2137(3) 0.8273(4) 0.131(2) Uani 1 1 d . . . H7 H 0.5807 0.2392 0.7794 0.157 Uiso 1 1 d R . . C8 C 0.8487(16) 0.2042(3) 0.8584(6) 0.130(2) Uani 1 1 d . . . H8 H 0.9531 0.2245 0.8358 0.156 Uiso 1 1 d R . . C9 C 0.9272(11) 0.1655(3) 0.9241(5) 0.118(2) Uani 1 1 d . . . H9 H 1.0845 0.1590 0.9458 0.142 Uiso 1 1 d R . . C10 C 0.9148(10) 0.1167(2) 1.1349(4) 0.0901(16) Uani 1 1 d . . . C11 C 0.7626(11) 0.1135(3) 1.1890(5) 0.131(2) Uani 1 1 d . . . H11 H 0.6211 0.0980 1.1604 0.157 Uiso 1 1 d R . . C12 C 0.8066(16) 0.1333(3) 1.2833(6) 0.152(3) Uani 1 1 d . . . H12 H 0.7022 0.1296 1.3224 0.182 Uiso 1 1 d R . . C13 C 1.0083(18) 0.1567(3) 1.3210(5) 0.137(3) Uani 1 1 d . . . H13 H 1.0348 0.1718 1.3843 0.165 Uiso 1 1 d R . . C14 C 1.1588(12) 0.1597(3) 1.2688(6) 0.128(2) Uani 1 1 d . . . H14 H 1.3011 0.1752 1.2960 0.153 Uiso 1 1 d R . . C15 C 1.1117(12) 0.1395(2) 1.1773(5) 0.114(2) Uani 1 1 d . . . H15 H 1.2222 0.1417 1.1410 0.137 Uiso 1 1 d R . . N1 N 0.8829(9) 0.0192(2) 0.6363(4) 0.1239(18) Uani 1 1 d . . . O2 O 1.2322(9) 0.07603(18) 0.5455(4) 0.1513(18) Uani 1 1 d . . . H2 H 1.2698 0.0465 0.5459 0.227 Uiso 1 1 calc R . . O3 O 0.7355(7) 0.02802(16) 0.4703(3) 0.1314(16) Uani 1 1 d . . . O4 O 0.9626(7) 0.03680(17) 0.8275(3) 0.1228(14) Uani 1 1 d . . . C16 C 1.0431(13) 0.0802(3) 0.5848(4) 0.124(2) Uani 1 1 d . . . C17 C 0.972(2) 0.1334(4) 0.5805(5) 0.124(2) Uani 1 1 d . . . C18 C 1.1122(16) 0.1714(5) 0.6106(5) 0.163(4) Uani 1 1 d . . . H18 H 1.2637 0.1646 0.6343 0.196 Uiso 1 1 calc R . . C19 C 1.041(2) 0.2205(5) 0.6078(7) 0.181(4) Uani 1 1 d . . . H19 H 1.1467 0.2457 0.6274 0.217 Uiso 1 1 calc R . . C20 C 0.831(3) 0.2326(5) 0.5787(7) 0.171(4) Uani 1 1 d . . . H20 H 0.7877 0.2660 0.5799 0.205 Uiso 1 1 calc R . . C21 C 0.6690(19) 0.1950(6) 0.5452(6) 0.169(3) Uani 1 1 d . . . H21 H 0.5185 0.2031 0.5227 0.203 Uiso 1 1 calc R . . C22 C 0.742(2) 0.1447(4) 0.5469(5) 0.140(3) Uani 1 1 d . . . H22 H 0.6394 0.1191 0.5258 0.169 Uiso 1 1 calc R . . C23 C 0.8584(11) 0.0397(3) 0.5503(5) 0.124(2) Uani 1 1 d . . . C24 C 1.0759(11) 0.0520(3) 0.6850(5) 0.133(2) Uani 1 1 d . . . H24 H 1.2167 0.0333 0.7028 0.159 Uiso 1 1 calc R . . C25 C 1.0244(11) 0.0747(3) 0.7690(5) 0.143(3) Uani 1 1 d . . . H25A H 1.1537 0.0928 0.8068 0.171 Uiso 1 1 calc R . . H25B H 0.9028 0.0984 0.7478 0.171 Uiso 1 1 calc R . . C26 C 0.7578(12) 0.0125(3) 0.7781(5) 0.143(3) Uani 1 1 d . . . H26A H 0.6401 0.0374 0.7607 0.172 Uiso 1 1 calc R . . H26B H 0.7167 -0.0113 0.8222 0.172 Uiso 1 1 calc R . . C27 C 0.7748(12) -0.0134(3) 0.6915(5) 0.147(3) Uani 1 1 d . . . H27A H 0.6272 -0.0225 0.6524 0.177 Uiso 1 1 calc R . . H27B H 0.8611 -0.0439 0.7090 0.177 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 0.113(3) 0.094(3) 0.091(2) 0.002(2) 0.0317(19) 0.001(2) C1 0.133(6) 0.080(6) 0.087(4) 0.008(4) 0.036(4) 0.002(4) C2 0.125(5) 0.073(4) 0.095(4) 0.000(4) 0.037(3) -0.013(4) C3 0.116(4) 0.082(4) 0.073(4) 0.003(3) 0.026(3) -0.006(4) C4 0.098(4) 0.083(5) 0.081(4) -0.006(4) 0.019(3) -0.004(4) C5 0.169(7) 0.106(6) 0.123(5) 0.051(5) -0.005(5) -0.033(5) C6 0.147(6) 0.163(8) 0.179(7) 0.059(7) -0.013(6) -0.026(6) C7 0.174(7) 0.109(6) 0.097(5) 0.020(4) 0.010(5) -0.006(6) C8 0.169(7) 0.110(6) 0.126(6) 0.016(5) 0.064(5) 0.002(5) C9 0.144(5) 0.095(5) 0.121(5) 0.028(4) 0.045(4) 0.000(5) C10 0.112(4) 0.085(4) 0.082(4) 0.012(3) 0.040(4) 0.001(3) C11 0.152(5) 0.127(6) 0.105(5) -0.011(4) 0.016(5) -0.007(4) C12 0.197(8) 0.170(8) 0.104(6) -0.006(5) 0.064(5) 0.018(6) C13 0.212(9) 0.090(6) 0.095(5) -0.012(4) 0.014(6) -0.006(5) C14 0.160(6) 0.125(6) 0.099(5) 0.000(4) 0.034(5) -0.036(4) C15 0.154(6) 0.102(5) 0.088(5) -0.011(4) 0.035(4) -0.033(4) N1 0.155(4) 0.127(5) 0.081(4) -0.001(4) 0.015(3) -0.041(4) O2 0.178(4) 0.129(4) 0.153(4) -0.019(4) 0.055(3) -0.041(3) O3 0.176(4) 0.115(4) 0.100(3) -0.002(3) 0.029(3) -0.029(3) O4 0.157(3) 0.126(4) 0.085(3) 0.009(3) 0.029(2) -0.025(3) C16 0.160(6) 0.133(7) 0.083(4) 0.003(5) 0.037(4) -0.031(6) C17 0.182(8) 0.112(8) 0.082(4) 0.008(5) 0.040(5) -0.012(7) C18 0.241(9) 0.124(8) 0.108(5) -0.006(6) 0.018(5) -0.099(9) C19 0.280(13) 0.093(8) 0.153(8) 0.010(6) 0.026(9) -0.057(9) C20 0.238(11) 0.138(10) 0.139(8) 0.003(7) 0.053(8) -0.013(10) C21 0.246(11) 0.151(10) 0.124(6) 0.008(7) 0.073(6) -0.003(10) C22 0.196(9) 0.115(8) 0.120(5) 0.008(5) 0.057(6) -0.029(6) C23 0.162(6) 0.123(6) 0.077(5) 0.001(4) 0.015(4) -0.042(5) C24 0.155(5) 0.128(6) 0.111(5) 0.000(5) 0.028(4) -0.016(5) C25 0.193(6) 0.142(7) 0.101(5) -0.019(5) 0.053(4) -0.053(5) C26 0.177(6) 0.155(7) 0.111(5) -0.017(5) 0.061(5) -0.053(5) C27 0.204(6) 0.112(6) 0.127(6) 0.021(5) 0.046(5) -0.049(5) _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 1.434(5) . ? O1 H1 0.8200 . ? C1 C2 1.184(6) . ? C1 C1 1.426(13) 3_657 ? C2 C3 1.461(8) . ? C3 C4 1.498(7) . ? C3 C10 1.508(7) . ? C4 C5 1.336(8) . ? C4 C9 1.375(7) . ? C5 C6 1.385(9) . ? C5 H5 0.9602 . ? C6 C7 1.384(9) . ? C6 H6 0.9600 . ? C7 C8 1.308(8) . ? C7 H7 0.9599 . ? C8 C9 1.392(8) . ? C8 H8 0.9601 . ? C9 H9 0.9600 . ? C10 C15 1.358(7) . ? C10 C11 1.365(8) . ? C11 C12 1.399(9) . ? C11 H11 0.9600 . ? C12 C13 1.376(9) . ? C12 H12 0.9600 . ? C13 C14 1.336(9) . ? C13 H13 0.9599 . ? C14 C15 1.365(8) . ? C14 H14 0.9600 . ? C15 H15 0.9601 . ? N1 C23 1.311(7) . ? N1 C27 1.445(8) . ? N1 C24 1.500(7) . ? O2 C16 1.427(7) . ? O2 H2 0.8200 . ? O3 C23 1.232(6) . ? O4 C25 1.423(7) . ? O4 C26 1.437(7) . ? C16 C17 1.482(9) . ? C16 C23 1.558(9) . ? C16 C24 1.576(8) . ? C17 C18 1.335(9) . ? C17 C22 1.410(9) . ? C18 C19 1.377(12) . ? C18 H18 0.9300 . ? C19 C20 1.302(11) . ? C19 H19 0.9300 . ? C20 C21 1.412(11) . ? C20 H20 0.9300 . ? C21 C22 1.416(11) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C24 C25 1.444(8) . ? C24 H24 0.9800 . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 C27 1.439(8) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? 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 178.6(8) . 3_657 ? C1 C2 C3 178.4(6) . . ? O1 C3 C2 108.7(5) . . ? O1 C3 C4 109.5(4) . . ? C2 C3 C4 110.4(5) . . ? O1 C3 C10 106.5(4) . . ? C2 C3 C10 112.0(5) . . ? C4 C3 C10 109.5(5) . . ? C5 C4 C9 115.9(6) . . ? C5 C4 C3 121.4(6) . . ? C9 C4 C3 122.7(6) . . ? C4 C5 C6 123.3(7) . . ? C4 C5 H5 118.5 . . ? C6 C5 H5 118.2 . . ? C5 C6 C7 119.0(7) . . ? C5 C6 H6 122.5 . . ? C7 C6 H6 118.4 . . ? C8 C7 C6 119.0(7) . . ? C8 C7 H7 121.0 . . ? C6 C7 H7 120.0 . . ? C7 C8 C9 121.1(7) . . ? C7 C8 H8 119.4 . . ? C9 C8 H8 119.5 . . ? C4 C9 C8 121.7(6) . . ? C4 C9 H9 118.2 . . ? C8 C9 H9 120.0 . . ? C15 C10 C11 116.8(6) . . ? C15 C10 C3 122.0(5) . . ? C11 C10 C3 121.2(6) . . ? C10 C11 C12 121.6(7) . . ? C10 C11 H11 118.6 . . ? C12 C11 H11 119.8 . . ? C13 C12 C11 118.4(7) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 121.4 . . ? C14 C13 C12 120.5(7) . . ? C14 C13 H13 121.3 . . ? C12 C13 H13 118.1 . . ? C13 C14 C15 119.7(7) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.0 . . ? C10 C15 C14 123.1(6) . . ? C10 C15 H15 118.2 . . ? C14 C15 H15 118.7 . . ? C23 N1 C27 142.9(6) . . ? C23 N1 C24 94.1(5) . . ? C27 N1 C24 121.9(5) . . ? C16 O2 H2 109.5 . . ? C25 O4 C26 111.9(5) . . ? O2 C16 C17 109.0(7) . . ? O2 C16 C23 115.7(6) . . ? C17 C16 C23 117.6(7) . . ? O2 C16 C24 112.9(6) . . ? C17 C16 C24 117.5(6) . . ? C23 C16 C24 82.3(5) . . ? C18 C17 C22 117.6(9) . . ? C18 C17 C16 123.4(11) . . ? C22 C17 C16 118.9(9) . . ? C17 C18 C19 122.4(10) . . ? C17 C18 H18 118.8 . . ? C19 C18 H18 118.8 . . ? C20 C19 C18 122.1(12) . . ? C20 C19 H19 118.9 . . ? C18 C19 H19 118.9 . . ? C19 C20 C21 119.7(12) . . ? C19 C20 H20 120.1 . . ? C21 C20 H20 120.1 . . ? C20 C21 C22 118.1(10) . . ? C20 C21 H21 121.0 . . ? C22 C21 H21 121.0 . . ? C17 C22 C21 120.0(9) . . ? C17 C22 H22 120.0 . . ? C21 C22 H22 120.0 . . ? O3 C23 N1 130.4(6) . . ? O3 C23 C16 133.9(6) . . ? N1 C23 C16 95.7(5) . . ? C25 C24 N1 107.7(5) . . ? C25 C24 C16 122.7(7) . . ? N1 C24 C16 87.8(5) . . ? C25 C24 H24 111.9 . . ? N1 C24 H24 111.9 . . ? C16 C24 H24 111.9 . . ? O4 C25 C24 109.5(6) . . ? O4 C25 H25A 109.8 . . ? C24 C25 H25A 109.8 . . ? O4 C25 H25B 109.8 . . ? C24 C25 H25B 109.8 . . ? H25A C25 H25B 108.2 . . ? O4 C26 C27 112.5(5) . . ? O4 C26 H26A 109.1 . . ? C27 C26 H26A 109.1 . . ? O4 C26 H26B 109.1 . . ? C27 C26 H26B 109.1 . . ? H26A C26 H26B 107.8 . . ? C26 C27 N1 108.7(6) . . ? C26 C27 H27A 109.9 . . ? N1 C27 H27A 109.9 . . ? C26 C27 H27B 109.9 . . ? N1 C27 H27B 109.9 . . ? H27A C27 H27B 108.3 . . ? 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 -20(48) 3_657 . . . ? C1 C2 C3 O1 12(22) . . . . ? C1 C2 C3 C4 132(21) . . . . ? C1 C2 C3 C10 -106(21) . . . . ? O1 C3 C4 C5 153.1(5) . . . . ? C2 C3 C4 C5 33.4(7) . . . . ? C10 C3 C4 C5 -90.4(7) . . . . ? O1 C3 C4 C9 -28.6(7) . . . . ? C2 C3 C4 C9 -148.3(5) . . . . ? C10 C3 C4 C9 87.9(7) . . . . ? C9 C4 C5 C6 0.5(10) . . . . ? C3 C4 C5 C6 178.9(7) . . . . ? C4 C5 C6 C7 -0.5(12) . . . . ? C5 C6 C7 C8 -0.3(12) . . . . ? C6 C7 C8 C9 1.1(11) . . . . ? C5 C4 C9 C8 0.2(9) . . . . ? C3 C4 C9 C8 -178.1(5) . . . . ? C7 C8 C9 C4 -1.1(10) . . . . ? O1 C3 C10 C15 35.1(7) . . . . ? C2 C3 C10 C15 153.9(5) . . . . ? C4 C3 C10 C15 -83.3(7) . . . . ? O1 C3 C10 C11 -144.2(6) . . . . ? C2 C3 C10 C11 -25.4(8) . . . . ? C4 C3 C10 C11 97.4(6) . . . . ? C15 C10 C11 C12 0.7(9) . . . . ? C3 C10 C11 C12 -179.9(6) . . . . ? C10 C11 C12 C13 0.4(11) . . . . ? C11 C12 C13 C14 -0.9(11) . . . . ? C12 C13 C14 C15 0.3(11) . . . . ? C11 C10 C15 C14 -1.4(9) . . . . ? C3 C10 C15 C14 179.2(6) . . . . ? C13 C14 C15 C10 1.0(10) . . . . ? O2 C16 C17 C18 -47.8(8) . . . . ? C23 C16 C17 C18 177.9(6) . . . . ? C24 C16 C17 C18 82.2(9) . . . . ? O2 C16 C17 C22 135.0(6) . . . . ? C23 C16 C17 C22 0.7(8) . . . . ? C24 C16 C17 C22 -95.0(8) . . . . ? C22 C17 C18 C19 -1.3(11) . . . . ? C16 C17 C18 C19 -178.6(7) . . . . ? C17 C18 C19 C20 2.4(15) . . . . ? C18 C19 C20 C21 -2.4(16) . . . . ? C19 C20 C21 C22 1.5(13) . . . . ? C18 C17 C22 C21 0.5(10) . . . . ? C16 C17 C22 C21 177.9(6) . . . . ? C20 C21 C22 C17 -0.6(11) . . . . ? C27 N1 C23 O3 -19.7(16) . . . . ? C24 N1 C23 O3 173.6(8) . . . . ? C27 N1 C23 C16 163.2(9) . . . . ? C24 N1 C23 C16 -3.6(6) . . . . ? O2 C16 C23 O3 -61.9(12) . . . . ? C17 C16 C23 O3 69.4(10) . . . . ? C24 C16 C23 O3 -173.6(9) . . . . ? O2 C16 C23 N1 115.1(6) . . . . ? C17 C16 C23 N1 -113.6(6) . . . . ? C24 C16 C23 N1 3.4(6) . . . . ? C23 N1 C24 C25 127.2(6) . . . . ? C27 N1 C24 C25 -43.4(9) . . . . ? C23 N1 C24 C16 3.5(6) . . . . ? C27 N1 C24 C16 -167.1(7) . . . . ? O2 C16 C24 C25 132.6(7) . . . . ? C17 C16 C24 C25 4.4(11) . . . . ? C23 C16 C24 C25 -112.7(7) . . . . ? O2 C16 C24 N1 -117.7(6) . . . . ? C17 C16 C24 N1 114.1(7) . . . . ? C23 C16 C24 N1 -3.0(5) . . . . ? C26 O4 C25 C24 -65.7(7) . . . . ? N1 C24 C25 O4 52.1(7) . . . . ? C16 C24 C25 O4 151.2(6) . . . . ? C25 O4 C26 C27 62.8(8) . . . . ? O4 C26 C27 N1 -46.2(8) . . . . ? C23 N1 C27 C26 -124.5(10) . . . . ? C24 N1 C27 C26 39.8(9) . . . . ? _diffrn_measured_fraction_theta_max 0.846 _diffrn_reflns_theta_full 25.09 _diffrn_measured_fraction_theta_full 0.846 _refine_diff_density_max 0.287 _refine_diff_density_min -0.164 _refine_diff_density_rms 0.043 # Attachment 'IIIa.cif' data_IIIa _database_code_depnum_ccdc_archive 'CCDC 664466' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,5-diphenylhydroquinone, 4-oxo(phenylacetyl)morpholine clathrate ; _chemical_name_common ;2,5-diphenylhydroquinone, 4-oxo(phenylacetyl)morpholine clathrate ; _chemical_melting_point ? _chemical_formula_moiety 'C30 H27 N O5' _chemical_formula_sum 'C30 H27 N O5' _chemical_formula_weight 481.53 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.6505(4) _cell_length_b 18.1949(8) _cell_length_c 10.6107(6) _cell_angle_alpha 90.00 _cell_angle_beta 105.147(3) _cell_angle_gamma 90.00 _cell_volume 2543.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4658 _cell_measurement_theta_min 1.018 _cell_measurement_theta_max 25.08 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.257 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 0.086 _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 ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4474 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0941 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 25.05 _reflns_number_total 4474 _reflns_number_gt 1994 _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^)+(0.0890P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.020(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4474 _refine_ls_number_parameters 345 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.1550 _refine_ls_R_factor_gt 0.0577 _refine_ls_wR_factor_ref 0.1722 _refine_ls_wR_factor_gt 0.1450 _refine_ls_goodness_of_fit_ref 0.919 _refine_ls_restrained_S_all 0.920 _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 -0.08748(14) 0.02718(13) 0.2024(2) 0.0647(7) Uani 1 1 d . . . H1OA H -0.1494 0.0271 0.1736 0.097 Uiso 1 1 calc R . . C1A C -0.1012(2) 0.01279(16) -0.0256(3) 0.0483(8) Uani 1 1 d . . . H1A H -0.1704 0.0219 -0.0412 0.058 Uiso 1 1 calc R . . C2A C -0.0428(2) 0.01323(15) 0.1023(3) 0.0473(8) Uani 1 1 d . . . C3A C 0.0622(2) 0.00053(15) 0.1319(3) 0.0461(8) Uani 1 1 d . . . C4A C 0.1311(2) 0.00250(16) 0.2659(3) 0.0501(8) Uani 1 1 d . . . C5A C 0.1007(3) -0.01730(18) 0.3759(3) 0.0655(10) Uani 1 1 d . . . H5A H 0.0346 -0.0336 0.3668 0.079 Uiso 1 1 calc R . . C6A C 0.1672(3) -0.0132(2) 0.4996(4) 0.0810(12) Uani 1 1 d . . . H6A H 0.1454 -0.0272 0.5721 0.097 Uiso 1 1 calc R . . C7A C 0.2648(3) 0.0113(2) 0.5157(4) 0.0842(12) Uani 1 1 d . . . H7A H 0.3085 0.0151 0.5989 0.101 Uiso 1 1 calc R . . C8A C 0.2972(3) 0.0302(2) 0.4088(4) 0.0749(11) Uani 1 1 d . . . H8A H 0.3635 0.0463 0.4192 0.090 Uiso 1 1 calc R . . C9A C 0.2318(2) 0.02557(17) 0.2852(3) 0.0614(9) Uani 1 1 d . . . H9A H 0.2553 0.0380 0.2133 0.074 Uiso 1 1 calc R . . O1B O 0.70101(13) -0.01808(12) 0.1378(2) 0.0631(7) Uani 1 1 d . . . H1OB H 0.7088 -0.0590 0.1713 0.095 Uiso 1 1 calc R . . C1B C 0.5281(2) -0.06015(16) 0.0782(3) 0.0524(8) Uani 1 1 d . . . H1B H 0.5476 -0.1008 0.1320 0.063 Uiso 1 1 calc R . . C2B C 0.60013(19) -0.00887(17) 0.0701(3) 0.0493(8) Uani 1 1 d . . . C3B C 0.5736(2) 0.05320(17) -0.0080(3) 0.0494(8) Uani 1 1 d . . . C4B C 0.6487(2) 0.11039(17) -0.0204(3) 0.0501(8) Uani 1 1 d . . . C5B C 0.6520(2) 0.1345(2) -0.1422(4) 0.0728(11) Uani 1 1 d . . . H5B H 0.6078 0.1145 -0.2162 0.087 Uiso 1 1 calc R . . C6B C 0.7203(3) 0.1883(2) -0.1561(5) 0.0908(13) Uani 1 1 d . . . H6B H 0.7217 0.2041 -0.2389 0.109 Uiso 1 1 calc R . . C7B C 0.7856(3) 0.2178(2) -0.0484(5) 0.0863(13) Uani 1 1 d . . . H7B H 0.8318 0.2536 -0.0578 0.104 Uiso 1 1 calc R . . C8B C 0.7833(2) 0.1950(2) 0.0736(5) 0.0725(11) Uani 1 1 d . . . H8B H 0.8279 0.2154 0.1469 0.087 Uiso 1 1 calc R . . C9B C 0.7147(2) 0.14147(18) 0.0885(3) 0.0592(9) Uani 1 1 d . . . H9B H 0.7131 0.1264 0.1717 0.071 Uiso 1 1 calc R . . O2 O 0.27054(18) 0.19798(15) 0.0902(3) 0.0886(9) Uani 1 1 d . . . O3 O 0.27338(16) 0.34847(13) 0.2393(2) 0.0761(8) Uani 1 1 d . . . C10 C 0.2996(2) 0.22399(19) 0.1994(4) 0.0641(10) Uani 1 1 d . . . C11 C 0.3953(2) 0.20190(18) 0.2923(4) 0.0599(9) Uani 1 1 d . . . C12 C 0.4229(3) 0.22864(19) 0.4181(4) 0.0718(10) Uani 1 1 d . . . H12 H 0.3819 0.2628 0.4449 0.086 Uiso 1 1 calc R . . C13 C 0.5116(3) 0.2048(2) 0.5048(4) 0.0901(13) Uani 1 1 d . . . H13 H 0.5300 0.2228 0.5898 0.108 Uiso 1 1 calc R . . C14 C 0.5721(3) 0.1546(2) 0.4650(5) 0.0920(13) Uani 1 1 d . . . H14 H 0.6318 0.1387 0.5230 0.110 Uiso 1 1 calc R . . C15 C 0.5453(3) 0.1279(2) 0.3407(5) 0.0897(13) Uani 1 1 d . . . H15 H 0.5867 0.0937 0.3147 0.108 Uiso 1 1 calc R . . C16 C 0.4580(3) 0.1509(2) 0.2537(4) 0.0751(11) Uani 1 1 d . . . H16 H 0.4405 0.1325 0.1690 0.090 Uiso 1 1 calc R . . C17 C 0.2383(3) 0.2863(2) 0.2360(3) 0.0650(10) Uani 1 1 d . A . N1 N 0.1466(2) 0.27106(16) 0.2509(4) 0.0938(11) Uani 1 1 d D . . O4 O -0.01308(18) 0.24072(14) 0.3588(3) 0.1009(10) Uani 1 1 d D . . C18 C 0.0706(5) 0.3277(3) 0.2536(7) 0.081(2) Uani 0.720(6) 1 d PD A 1 H18A H 0.0146 0.3249 0.1756 0.097 Uiso 0.720(6) 1 calc PR A 1 H18B H 0.1005 0.3763 0.2584 0.097 Uiso 0.720(6) 1 calc PR A 1 C19 C 0.0336(5) 0.3122(3) 0.3756(7) 0.086(2) Uani 0.720(6) 1 d PD A 1 H19A H 0.0903 0.3129 0.4530 0.103 Uiso 0.720(6) 1 calc PR A 1 H19B H -0.0151 0.3492 0.3852 0.103 Uiso 0.720(6) 1 calc PR A 1 C20 C 0.0640(5) 0.1857(3) 0.3617(7) 0.0779(19) Uani 0.720(6) 1 d PD A 1 H20A H 0.0365 0.1368 0.3646 0.093 Uiso 0.720(6) 1 calc PR A 1 H20B H 0.1208 0.1923 0.4378 0.093 Uiso 0.720(6) 1 calc PR A 1 C21 C 0.0982(4) 0.1960(2) 0.2363(6) 0.0703(18) Uani 0.720(6) 1 d PD A 1 H21A H 0.1467 0.1584 0.2285 0.084 Uiso 0.720(6) 1 calc PR A 1 H21B H 0.0407 0.1941 0.1600 0.084 Uiso 0.720(6) 1 calc PR A 1 C22 C 0.1481(9) 0.2043(6) 0.3280(15) 0.084(5) Uiso 0.280(6) 1 d PD A 2 H22A H 0.1752 0.2134 0.4207 0.101 Uiso 0.280(6) 1 calc PR A 2 H22B H 0.1867 0.1653 0.3009 0.101 Uiso 0.280(6) 1 calc PR A 2 C23 C -0.0023(9) 0.3084(6) 0.2898(16) 0.083(5) Uiso 0.280(6) 1 d PD A 2 H23A H -0.0295 0.3014 0.1966 0.100 Uiso 0.280(6) 1 calc PR A 2 H23B H -0.0402 0.3476 0.3174 0.100 Uiso 0.280(6) 1 calc PR A 2 C24 C 0.1042(8) 0.3285(8) 0.3179(16) 0.078(6) Uiso 0.280(6) 1 d PD A 2 H24A H 0.1357 0.3281 0.4111 0.094 Uiso 0.280(6) 1 calc PR A 2 H24B H 0.1126 0.3768 0.2833 0.094 Uiso 0.280(6) 1 calc PR A 2 C25 C 0.0343(8) 0.1864(7) 0.2938(15) 0.066(5) Uiso 0.280(6) 1 d PD A 2 H25A H 0.0055 0.1887 0.2001 0.079 Uiso 0.280(6) 1 calc PR A 2 H25B H 0.0236 0.1374 0.3236 0.079 Uiso 0.280(6) 1 calc PR A 2 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 0.0522(12) 0.0893(17) 0.0556(15) -0.0052(12) 0.0192(11) 0.0054(12) C1A 0.0417(16) 0.053(2) 0.050(2) 0.0012(15) 0.0126(15) 0.0020(13) C2A 0.0531(18) 0.0436(18) 0.051(2) -0.0048(15) 0.0242(16) -0.0011(13) C3A 0.0456(17) 0.0439(18) 0.048(2) -0.0012(15) 0.0120(15) -0.0009(13) C4A 0.0562(19) 0.0468(19) 0.047(2) -0.0003(15) 0.0129(16) 0.0051(14) C5A 0.070(2) 0.067(2) 0.058(2) -0.0024(18) 0.0129(19) 0.0062(17) C6A 0.091(3) 0.095(3) 0.057(3) 0.000(2) 0.018(2) 0.019(2) C7A 0.086(3) 0.092(3) 0.063(3) -0.012(2) -0.001(2) 0.021(2) C8A 0.062(2) 0.078(3) 0.072(3) -0.006(2) -0.004(2) 0.0017(18) C9A 0.057(2) 0.062(2) 0.060(2) 0.0009(17) 0.0069(17) 0.0035(16) O1B 0.0432(12) 0.0678(15) 0.0732(17) 0.0134(13) 0.0062(11) 0.0016(10) C1B 0.0493(18) 0.054(2) 0.055(2) 0.0066(16) 0.0163(16) 0.0029(15) C2B 0.0383(17) 0.059(2) 0.050(2) 0.0005(16) 0.0106(15) 0.0022(14) C3B 0.0438(18) 0.055(2) 0.051(2) 0.0009(16) 0.0152(15) -0.0004(14) C4B 0.0440(17) 0.053(2) 0.057(2) 0.0031(16) 0.0200(16) 0.0035(14) C5B 0.066(2) 0.091(3) 0.064(3) 0.014(2) 0.0194(19) -0.0118(19) C6B 0.084(3) 0.104(3) 0.091(3) 0.029(3) 0.034(3) -0.014(2) C7B 0.067(2) 0.083(3) 0.117(4) 0.011(3) 0.038(3) -0.014(2) C8B 0.052(2) 0.070(3) 0.097(3) -0.016(2) 0.022(2) -0.0058(18) C9B 0.0487(18) 0.067(2) 0.064(2) -0.0080(18) 0.0191(17) -0.0018(16) O2 0.0804(17) 0.106(2) 0.076(2) -0.0183(17) 0.0149(15) -0.0017(14) O3 0.0745(15) 0.0620(17) 0.089(2) 0.0006(14) 0.0166(13) -0.0117(13) C10 0.063(2) 0.064(2) 0.068(3) -0.001(2) 0.0230(19) -0.0059(17) C11 0.058(2) 0.060(2) 0.066(3) 0.0011(19) 0.0244(18) -0.0004(17) C12 0.078(2) 0.069(2) 0.068(3) -0.006(2) 0.017(2) 0.0142(18) C13 0.098(3) 0.089(3) 0.077(3) -0.005(2) 0.009(2) 0.015(2) C14 0.080(3) 0.105(4) 0.085(3) 0.006(3) 0.013(2) 0.021(2) C15 0.075(3) 0.104(3) 0.095(4) 0.010(3) 0.033(2) 0.030(2) C16 0.079(2) 0.082(3) 0.073(3) -0.001(2) 0.036(2) 0.008(2) C17 0.059(2) 0.060(2) 0.075(3) 0.0053(19) 0.0150(19) -0.0034(18) N1 0.086(2) 0.0429(18) 0.170(4) 0.0052(19) 0.065(2) 0.0125(16) O4 0.0800(16) 0.0624(17) 0.176(3) -0.0209(18) 0.0613(18) 0.0021(14) C18 0.055(3) 0.049(3) 0.131(6) 0.001(3) 0.011(4) 0.016(2) C19 0.079(4) 0.058(4) 0.119(6) -0.031(3) 0.022(4) 0.013(3) C20 0.082(4) 0.047(3) 0.109(6) -0.008(3) 0.033(4) 0.002(3) C21 0.062(3) 0.040(3) 0.110(5) -0.021(3) 0.025(3) -0.002(2) _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 C2A 1.380(4) . ? O1A H1OA 0.8200 . ? C1A C2A 1.383(4) . ? C1A C3A 1.389(4) 3 ? C1A H1A 0.9300 . ? C2A C3A 1.403(4) . ? C3A C1A 1.389(4) 3 ? C3A C4A 1.487(4) . ? C4A C5A 1.386(4) . ? C4A C9A 1.400(4) . ? C5A C6A 1.389(4) . ? C5A H5A 0.9300 . ? C6A C7A 1.373(5) . ? C6A H6A 0.9300 . ? C7A C8A 1.364(5) . ? C7A H7A 0.9300 . ? C8A C9A 1.383(4) . ? C8A H8A 0.9300 . ? C9A H9A 0.9300 . ? O1B C2B 1.387(3) . ? O1B H1OB 0.8200 . ? C1B C2B 1.374(4) . ? C1B C3B 1.399(4) 3_655 ? C1B H1B 0.9300 . ? C2B C3B 1.392(4) . ? C3B C1B 1.399(4) 3_655 ? C3B C4B 1.491(4) . ? C4B C5B 1.377(4) . ? C4B C9B 1.387(4) . ? C5B C6B 1.385(5) . ? C5B H5B 0.9300 . ? C6B C7B 1.363(5) . ? C6B H6B 0.9300 . ? C7B C8B 1.368(5) . ? C7B H7B 0.9300 . ? C8B C9B 1.388(5) . ? C8B H8B 0.9300 . ? C9B H9B 0.9300 . ? O2 C10 1.217(4) . ? O3 C17 1.225(4) . ? C10 C11 1.472(5) . ? C10 C17 1.519(5) . ? C11 C12 1.377(4) . ? C11 C16 1.395(5) . ? C12 C13 1.385(5) . ? C12 H12 0.9300 . ? C13 C14 1.371(5) . ? C13 H13 0.9300 . ? C14 C15 1.363(5) . ? C14 H14 0.9300 . ? C15 C16 1.367(5) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 N1 1.331(4) . ? N1 C22 1.462(5) . ? N1 C24 1.466(5) . ? N1 C18 1.468(5) . ? N1 C21 1.507(5) . ? O4 C19 1.438(6) . ? O4 C20 1.447(5) . ? O4 C25 1.450(5) . ? O4 C23 1.460(5) . ? C18 C19 1.534(4) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.532(4) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C25 1.535(5) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.452(5) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? 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 C2A O1A H1OA 109.5 . . ? C2A C1A C3A 123.5(3) . 3 ? C2A C1A H1A 118.2 . . ? C3A C1A H1A 118.2 3 . ? O1A C2A C1A 119.9(3) . . ? O1A C2A C3A 119.3(3) . . ? C1A C2A C3A 120.8(3) . . ? C1A C3A C2A 115.7(3) 3 . ? C1A C3A C4A 120.0(3) 3 . ? C2A C3A C4A 124.3(3) . . ? C5A C4A C9A 117.0(3) . . ? C5A C4A C3A 123.0(3) . . ? C9A C4A C3A 120.0(3) . . ? C4A C5A C6A 121.1(3) . . ? C4A C5A H5A 119.5 . . ? C6A C5A H5A 119.5 . . ? C7A C6A C5A 120.6(4) . . ? C7A C6A H6A 119.7 . . ? C5A C6A H6A 119.7 . . ? C8A C7A C6A 119.6(4) . . ? C8A C7A H7A 120.2 . . ? C6A C7A H7A 120.2 . . ? C7A C8A C9A 120.2(4) . . ? C7A C8A H8A 119.9 . . ? C9A C8A H8A 119.9 . . ? C8A C9A C4A 121.5(4) . . ? C8A C9A H9A 119.2 . . ? C4A C9A H9A 119.2 . . ? C2B O1B H1OB 109.5 . . ? C2B C1B C3B 122.2(3) . 3_655 ? C2B C1B H1B 118.9 . . ? C3B C1B H1B 118.9 3_655 . ? C1B C2B O1B 121.0(3) . . ? C1B C2B C3B 120.6(2) . . ? O1B C2B C3B 118.4(3) . . ? C2B C3B C1B 117.3(3) . 3_655 ? C2B C3B C4B 122.7(2) . . ? C1B C3B C4B 120.0(3) 3_655 . ? C5B C4B C9B 118.6(3) . . ? C5B C4B C3B 119.8(3) . . ? C9B C4B C3B 121.6(3) . . ? C4B C5B C6B 120.8(4) . . ? C4B C5B H5B 119.6 . . ? C6B C5B H5B 119.6 . . ? C7B C6B C5B 120.0(4) . . ? C7B C6B H6B 120.0 . . ? C5B C6B H6B 120.0 . . ? C6B C7B C8B 120.1(4) . . ? C6B C7B H7B 119.9 . . ? C8B C7B H7B 119.9 . . ? C7B C8B C9B 120.3(4) . . ? C7B C8B H8B 119.9 . . ? C9B C8B H8B 119.9 . . ? C4B C9B C8B 120.1(4) . . ? C4B C9B H9B 119.9 . . ? C8B C9B H9B 119.9 . . ? O2 C10 C11 122.9(3) . . ? O2 C10 C17 118.0(3) . . ? C11 C10 C17 118.9(3) . . ? C12 C11 C16 119.0(3) . . ? C12 C11 C10 121.6(3) . . ? C16 C11 C10 119.4(4) . . ? C11 C12 C13 120.3(4) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C14 C13 C12 119.7(4) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C15 C14 C13 120.3(4) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C14 C15 C16 120.7(4) . . ? C14 C15 H15 119.6 . . ? C16 C15 H15 119.6 . . ? C15 C16 C11 119.9(4) . . ? C15 C16 H16 120.1 . . ? C11 C16 H16 120.1 . . ? O3 C17 N1 124.2(3) . . ? O3 C17 C10 117.3(3) . . ? N1 C17 C10 118.2(3) . . ? C17 N1 C22 111.4(5) . . ? C17 N1 C24 114.3(6) . . ? C22 N1 C24 105.7(11) . . ? C17 N1 C18 123.2(4) . . ? C22 N1 C18 118.6(7) . . ? C24 N1 C18 28.2(6) . . ? C17 N1 C21 125.3(3) . . ? C22 N1 C21 41.1(6) . . ? C24 N1 C21 118.5(7) . . ? C18 N1 C21 110.1(4) . . ? C19 O4 C20 109.1(4) . . ? C19 O4 C25 115.9(7) . . ? C20 O4 C25 29.1(6) . . ? C19 O4 C23 36.9(6) . . ? C20 O4 C23 115.3(7) . . ? C25 O4 C23 102.8(11) . . ? N1 C18 C19 106.1(4) . . ? N1 C18 H18A 110.5 . . ? C19 C18 H18A 110.5 . . ? N1 C18 H18B 110.5 . . ? C19 C18 H18B 110.5 . . ? H18A C18 H18B 108.7 . . ? O4 C19 C18 107.2(5) . . ? O4 C19 H19A 110.3 . . ? C18 C19 H19A 110.3 . . ? O4 C19 H19B 110.3 . . ? C18 C19 H19B 110.3 . . ? H19A C19 H19B 108.5 . . ? O4 C20 C21 106.3(4) . . ? O4 C20 H20A 110.5 . . ? C21 C20 H20A 110.5 . . ? O4 C20 H20B 110.5 . . ? C21 C20 H20B 110.5 . . ? H20A C20 H20B 108.7 . . ? N1 C21 C20 104.3(4) . . ? N1 C21 H21A 110.9 . . ? C20 C21 H21A 110.9 . . ? N1 C21 H21B 110.9 . . ? C20 C21 H21B 110.9 . . ? H21A C21 H21B 108.9 . . ? N1 C22 C25 100.3(10) . . ? N1 C22 H22A 111.7 . . ? C25 C22 H22A 111.7 . . ? N1 C22 H22B 111.7 . . ? C25 C22 H22B 111.7 . . ? H22A C22 H22B 109.5 . . ? C24 C23 O4 109.6(11) . . ? C24 C23 H23A 109.7 . . ? O4 C23 H23A 109.7 . . ? C24 C23 H23B 109.7 . . ? O4 C23 H23B 109.7 . . ? H23A C23 H23B 108.2 . . ? C23 C24 N1 102.9(10) . . ? C23 C24 H24A 111.2 . . ? N1 C24 H24A 111.2 . . ? C23 C24 H24B 111.2 . . ? N1 C24 H24B 111.2 . . ? H24A C24 H24B 109.1 . . ? O4 C25 C22 107.0(9) . . ? O4 C25 H25A 110.3 . . ? C22 C25 H25A 110.3 . . ? O4 C25 H25B 110.3 . . ? C22 C25 H25B 110.3 . . ? H25A C25 H25B 108.6 . . ? 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 C3A C1A C2A O1A 179.8(3) 3 . . . ? C3A C1A C2A C3A 0.6(5) 3 . . . ? O1A C2A C3A C1A -179.8(3) . . . 3 ? C1A C2A C3A C1A -0.6(5) . . . 3 ? O1A C2A C3A C4A -1.4(4) . . . . ? C1A C2A C3A C4A 177.8(3) . . . . ? C1A C3A C4A C5A -150.2(3) 3 . . . ? C2A C3A C4A C5A 31.5(4) . . . . ? C1A C3A C4A C9A 30.2(4) 3 . . . ? C2A C3A C4A C9A -148.1(3) . . . . ? C9A C4A C5A C6A 0.9(5) . . . . ? C3A C4A C5A C6A -178.7(3) . . . . ? C4A C5A C6A C7A 0.6(5) . . . . ? C5A C6A C7A C8A -1.5(6) . . . . ? C6A C7A C8A C9A 0.8(6) . . . . ? C7A C8A C9A C4A 0.8(5) . . . . ? C5A C4A C9A C8A -1.7(4) . . . . ? C3A C4A C9A C8A 178.0(3) . . . . ? C3B C1B C2B O1B -178.1(3) 3_655 . . . ? C3B C1B C2B C3B 0.9(5) 3_655 . . . ? C1B C2B C3B C1B -0.9(5) . . . 3_655 ? O1B C2B C3B C1B 178.2(3) . . . 3_655 ? C1B C2B C3B C4B -179.9(3) . . . . ? O1B C2B C3B C4B -0.8(5) . . . . ? C2B C3B C4B C5B 131.3(3) . . . . ? C1B C3B C4B C5B -47.7(4) 3_655 . . . ? C2B C3B C4B C9B -50.1(4) . . . . ? C1B C3B C4B C9B 130.9(3) 3_655 . . . ? C9B C4B C5B C6B 0.6(5) . . . . ? C3B C4B C5B C6B 179.2(3) . . . . ? C4B C5B C6B C7B 0.1(6) . . . . ? C5B C6B C7B C8B -0.5(6) . . . . ? C6B C7B C8B C9B 0.1(6) . . . . ? C5B C4B C9B C8B -0.9(5) . . . . ? C3B C4B C9B C8B -179.5(3) . . . . ? C7B C8B C9B C4B 0.6(5) . . . . ? O2 C10 C11 C12 -175.6(3) . . . . ? C17 C10 C11 C12 9.6(5) . . . . ? O2 C10 C11 C16 2.3(5) . . . . ? C17 C10 C11 C16 -172.5(3) . . . . ? C16 C11 C12 C13 -0.3(5) . . . . ? C10 C11 C12 C13 177.6(3) . . . . ? C11 C12 C13 C14 0.2(6) . . . . ? C12 C13 C14 C15 -0.2(7) . . . . ? C13 C14 C15 C16 0.3(7) . . . . ? C14 C15 C16 C11 -0.3(6) . . . . ? C12 C11 C16 C15 0.3(5) . . . . ? C10 C11 C16 C15 -177.6(3) . . . . ? O2 C10 C17 O3 -104.6(4) . . . . ? C11 C10 C17 O3 70.4(4) . . . . ? O2 C10 C17 N1 69.5(5) . . . . ? C11 C10 C17 N1 -115.5(4) . . . . ? O3 C17 N1 C22 -141.0(8) . . . . ? C10 C17 N1 C22 45.3(9) . . . . ? O3 C17 N1 C24 -21.2(10) . . . . ? C10 C17 N1 C24 165.1(9) . . . . ? O3 C17 N1 C18 9.5(7) . . . . ? C10 C17 N1 C18 -164.2(5) . . . . ? O3 C17 N1 C21 174.6(4) . . . . ? C10 C17 N1 C21 0.9(6) . . . . ? C17 N1 C18 C19 -129.8(5) . . . . ? C22 N1 C18 C19 18.7(10) . . . . ? C24 N1 C18 C19 -49.9(15) . . . . ? C21 N1 C18 C19 63.1(6) . . . . ? C20 O4 C19 C18 67.3(6) . . . . ? C25 O4 C19 C18 36.6(9) . . . . ? C23 O4 C19 C18 -39.7(11) . . . . ? N1 C18 C19 O4 -62.4(7) . . . . ? C19 O4 C20 C21 -69.3(6) . . . . ? C25 O4 C20 C21 39.9(13) . . . . ? C23 O4 C20 C21 -29.9(10) . . . . ? C17 N1 C21 C20 128.8(5) . . . . ? C22 N1 C21 C20 46.4(9) . . . . ? C24 N1 C21 C20 -34.7(10) . . . . ? C18 N1 C21 C20 -64.5(6) . . . . ? O4 C20 C21 N1 64.7(6) . . . . ? C17 N1 C22 C25 -162.9(7) . . . . ? C24 N1 C22 C25 72.4(11) . . . . ? C18 N1 C22 C25 45.1(13) . . . . ? C21 N1 C22 C25 -43.2(5) . . . . ? C19 O4 C23 C24 48.9(8) . . . . ? C20 O4 C23 C24 -39.5(16) . . . . ? C25 O4 C23 C24 -67.4(14) . . . . ? O4 C23 C24 N1 69.0(17) . . . . ? C17 N1 C24 C23 165.0(9) . . . . ? C22 N1 C24 C23 -72.1(13) . . . . ? C18 N1 C24 C23 49.7(8) . . . . ? C21 N1 C24 C23 -29.7(15) . . . . ? C19 O4 C25 C22 31.1(14) . . . . ? C20 O4 C25 C22 -51.7(8) . . . . ? C23 O4 C25 C22 67.8(13) . . . . ? N1 C22 C25 O4 -71.7(14) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.305 _refine_diff_density_min -0.300 _refine_diff_density_rms 0.078 # Attachment 'Vb.cif' data_Vb _database_code_depnum_ccdc_archive 'CCDC 664467' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,1,2,2-tetraphenyl-1,2-ethandiol, 1-(phenylglyoxylyl)piperidine clathrate ; _chemical_name_common ;1,1,2,2-tetraphenyl-1,2-ethandiol, 1- (phenylglyoxylyl)piperidine clathrate ; _chemical_melting_point ? _chemical_formula_moiety 'C26 H22 O2, C13 H15 N O2' _chemical_formula_sum 'C39 H37 N O4' _chemical_formula_weight 583.70 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.7197(3) _cell_length_b 20.9418(7) _cell_length_c 15.7092(4) _cell_angle_alpha 90.00 _cell_angle_beta 99.747(3) _cell_angle_gamma 90.00 _cell_volume 3151.41(16) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.230 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1240 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9806 _exptl_absorpt_correction_T_max 0.9922 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1998)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'Bruker SMART 6K CCD Detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 8 _diffrn_standards_number none _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 19518 _diffrn_reflns_av_R_equivalents 0.0386 _diffrn_reflns_av_sigmaI/netI 0.0574 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 25.05 _reflns_number_total 5579 _reflns_number_gt 4198 _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^)+(0.1028P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5579 _refine_ls_number_parameters 399 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0588 _refine_ls_R_factor_gt 0.0389 _refine_ls_wR_factor_ref 0.1388 _refine_ls_wR_factor_gt 0.1210 _refine_ls_goodness_of_fit_ref 0.908 _refine_ls_restrained_S_all 0.908 _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 0.38497(12) 0.09969(5) 0.20356(7) 0.0263(3) Uani 1 1 d . . . H1 H 0.3928 0.1392 0.2121 0.039 Uiso 1 1 calc R . . O2 O 0.53914(12) -0.02763(5) 0.34552(7) 0.0294(3) Uani 1 1 d . . . H2 H 0.5833 -0.0612 0.3388 0.044 Uiso 1 1 calc R . . C1 C 0.42094(17) 0.06644(7) 0.28467(10) 0.0239(4) Uani 1 1 d . . . C2 C 0.28602(17) 0.05995(7) 0.32462(10) 0.0253(4) Uani 1 1 d . . . C3 C 0.2606(2) 0.00888(9) 0.37724(12) 0.0368(4) Uani 1 1 d . . . H3 H 0.3244 -0.0258 0.3865 0.044 Uiso 1 1 calc R . . C4 C 0.1416(2) 0.00894(10) 0.41611(13) 0.0448(5) Uani 1 1 d . . . H4 H 0.1248 -0.0260 0.4515 0.054 Uiso 1 1 calc R . . C5 C 0.0467(2) 0.05962(9) 0.40379(12) 0.0414(5) Uani 1 1 d . . . H5 H -0.0329 0.0597 0.4315 0.050 Uiso 1 1 calc R . . C6 C 0.07035(18) 0.10978(9) 0.35056(12) 0.0352(4) Uani 1 1 d . . . H6 H 0.0056 0.1441 0.3406 0.042 Uiso 1 1 calc R . . C7 C 0.18890(17) 0.10994(8) 0.31172(11) 0.0288(4) Uani 1 1 d . . . H7 H 0.2043 0.1447 0.2757 0.035 Uiso 1 1 calc R . . C8 C 0.53267(17) 0.10469(7) 0.34788(10) 0.0247(4) Uani 1 1 d . . . C9 C 0.53817(18) 0.10303(8) 0.43788(11) 0.0294(4) Uani 1 1 d . . . H9 H 0.4738 0.0771 0.4614 0.035 Uiso 1 1 calc R . . C11 C 0.73419(18) 0.17706(8) 0.46155(11) 0.0307(4) Uani 1 1 d . . . H11 H 0.8014 0.2010 0.4995 0.037 Uiso 1 1 calc R . . C10 C 0.63704(19) 0.13900(8) 0.49359(11) 0.0331(4) Uani 1 1 d . . . H10 H 0.6377 0.1374 0.5541 0.040 Uiso 1 1 calc R . . C12 C 0.73052(17) 0.17916(7) 0.37237(11) 0.0275(4) Uani 1 1 d . . . H12 H 0.7954 0.2051 0.3492 0.033 Uiso 1 1 calc R . . C13 C 0.63134(17) 0.14311(7) 0.31639(11) 0.0253(4) Uani 1 1 d . . . H13 H 0.6312 0.1448 0.2559 0.030 Uiso 1 1 calc R . . C14 C 0.48689(17) 0.00013(7) 0.26228(10) 0.0250(4) Uani 1 1 d . . . C15 C 0.38007(17) -0.04639(8) 0.20726(10) 0.0258(4) Uani 1 1 d . . . C16 C 0.24606(18) -0.02967(8) 0.16279(11) 0.0289(4) Uani 1 1 d . . . H16 H 0.2125 0.0126 0.1672 0.035 Uiso 1 1 calc R . . C17 C 0.16117(19) -0.07519(8) 0.11179(11) 0.0331(4) Uani 1 1 d . . . H17 H 0.0706 -0.0635 0.0832 0.040 Uiso 1 1 calc R . . C18 C 0.21024(19) -0.13722(8) 0.10343(11) 0.0346(4) Uani 1 1 d . . . H18 H 0.1541 -0.1677 0.0686 0.041 Uiso 1 1 calc R . . C19 C 0.34386(19) -0.15407(8) 0.14727(12) 0.0339(4) Uani 1 1 d . . . H19 H 0.3780 -0.1961 0.1420 0.041 Uiso 1 1 calc R . . C20 C 0.42673(18) -0.10936(8) 0.19854(11) 0.0308(4) Uani 1 1 d . . . H20 H 0.5163 -0.1217 0.2281 0.037 Uiso 1 1 calc R . . C21 C 0.60777(17) 0.01150(7) 0.21139(10) 0.0235(4) Uani 1 1 d . . . C22 C 0.57785(17) 0.02716(7) 0.12303(10) 0.0259(4) Uani 1 1 d . . . H22 H 0.4836 0.0309 0.0950 0.031 Uiso 1 1 calc R . . C23 C 0.68532(18) 0.03711(8) 0.07666(11) 0.0303(4) Uani 1 1 d . . . H23 H 0.6644 0.0487 0.0174 0.036 Uiso 1 1 calc R . . C24 C 0.82568(18) 0.03008(8) 0.11703(12) 0.0317(4) Uani 1 1 d . . . H24 H 0.8988 0.0366 0.0848 0.038 Uiso 1 1 calc R . . C25 C 0.85705(18) 0.01358(8) 0.20383(12) 0.0317(4) Uani 1 1 d . . . H25 H 0.9514 0.0082 0.2308 0.038 Uiso 1 1 calc R . . C26 C 0.74921(17) 0.00493(7) 0.25119(11) 0.0276(4) Uani 1 1 d . . . H26 H 0.7709 -0.0055 0.3108 0.033 Uiso 1 1 calc R . . N1 N 0.34036(15) 0.24179(6) 0.04596(9) 0.0293(3) Uani 1 1 d . . . O3 O 0.26657(13) 0.36716(5) 0.14177(8) 0.0380(3) Uani 1 1 d . . . O4 O 0.39009(13) 0.23281(5) 0.19413(7) 0.0354(3) Uani 1 1 d . . . C27 C 0.08074(18) 0.29424(8) 0.15340(10) 0.0282(4) Uani 1 1 d . . . C28 C -0.00600(19) 0.34262(8) 0.17758(11) 0.0317(4) Uani 1 1 d . . . H28 H 0.0267 0.3854 0.1836 0.038 Uiso 1 1 calc R . . C29 C -0.1390(2) 0.32788(9) 0.19255(11) 0.0348(4) Uani 1 1 d . . . H29 H -0.1968 0.3605 0.2094 0.042 Uiso 1 1 calc R . . C30 C -0.1882(2) 0.26487(9) 0.18280(11) 0.0364(4) Uani 1 1 d . . . H30 H -0.2796 0.2550 0.1927 0.044 Uiso 1 1 calc R . . C31 C -0.10358(19) 0.21652(9) 0.15860(12) 0.0363(4) Uani 1 1 d . . . H31 H -0.1375 0.1739 0.1521 0.044 Uiso 1 1 calc R . . C32 C 0.03111(19) 0.23080(8) 0.14391(11) 0.0310(4) Uani 1 1 d . . . H32 H 0.0889 0.1980 0.1276 0.037 Uiso 1 1 calc R . . C33 C 0.22378(18) 0.31164(8) 0.13816(11) 0.0287(4) Uani 1 1 d . . . C34 C 0.32617(17) 0.25734(7) 0.12613(11) 0.0270(4) Uani 1 1 d . . . C35 C 0.25713(19) 0.27185(8) -0.03229(11) 0.0326(4) Uani 1 1 d . . . H35A H 0.3206 0.2934 -0.0662 0.039 Uiso 1 1 calc R . . H35B H 0.1938 0.3044 -0.0145 0.039 Uiso 1 1 calc R . . C36 C 0.17077(19) 0.22086(9) -0.08867(12) 0.0359(4) Uani 1 1 d . . . H36A H 0.0995 0.2029 -0.0573 0.043 Uiso 1 1 calc R . . H36B H 0.1220 0.2407 -0.1426 0.043 Uiso 1 1 calc R . . C37 C 0.2666(2) 0.16729(9) -0.11052(12) 0.0394(5) Uani 1 1 d . . . H37A H 0.3295 0.1844 -0.1485 0.047 Uiso 1 1 calc R . . H37B H 0.2092 0.1331 -0.1424 0.047 Uiso 1 1 calc R . . C38 C 0.3548(2) 0.13893(8) -0.02834(12) 0.0366(4) Uani 1 1 d . . . H38A H 0.2925 0.1165 0.0055 0.044 Uiso 1 1 calc R . . H38B H 0.4208 0.1072 -0.0451 0.044 Uiso 1 1 calc R . . C39 C 0.43724(18) 0.19059(8) 0.02836(11) 0.0320(4) Uani 1 1 d . . . H39A H 0.4838 0.1715 0.0835 0.038 Uiso 1 1 calc R . . H39B H 0.5101 0.2087 -0.0016 0.038 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 0.0342(6) 0.0226(6) 0.0226(6) 0.0036(4) 0.0060(5) 0.0031(5) O2 0.0386(7) 0.0245(6) 0.0251(6) 0.0029(5) 0.0050(5) 0.0074(5) C1 0.0279(9) 0.0227(8) 0.0212(8) 0.0028(6) 0.0042(7) 0.0009(6) C2 0.0279(9) 0.0273(9) 0.0207(8) -0.0037(6) 0.0039(7) -0.0019(6) C3 0.0410(11) 0.0374(10) 0.0347(10) 0.0074(8) 0.0144(9) 0.0026(8) C4 0.0462(12) 0.0524(12) 0.0390(11) 0.0118(9) 0.0163(10) -0.0037(9) C5 0.0360(10) 0.0566(13) 0.0356(10) -0.0061(9) 0.0176(9) -0.0079(9) C6 0.0288(9) 0.0401(10) 0.0377(10) -0.0090(8) 0.0084(8) -0.0006(8) C7 0.0284(9) 0.0311(9) 0.0268(9) -0.0023(7) 0.0049(7) -0.0013(7) C8 0.0296(9) 0.0201(8) 0.0248(8) 0.0008(6) 0.0060(7) 0.0045(6) C9 0.0336(9) 0.0274(9) 0.0279(9) 0.0022(7) 0.0069(7) -0.0004(7) C11 0.0337(10) 0.0251(9) 0.0307(9) -0.0026(7) -0.0020(8) 0.0009(7) C10 0.0428(11) 0.0308(9) 0.0244(9) 0.0005(7) 0.0025(8) 0.0010(7) C12 0.0285(9) 0.0221(8) 0.0322(9) 0.0013(7) 0.0059(7) 0.0028(6) C13 0.0298(9) 0.0224(8) 0.0243(8) 0.0005(6) 0.0063(7) 0.0034(6) C14 0.0288(9) 0.0225(8) 0.0238(8) 0.0029(6) 0.0049(7) 0.0017(6) C15 0.0295(9) 0.0259(8) 0.0239(8) -0.0007(7) 0.0101(7) -0.0038(7) C16 0.0359(10) 0.0263(9) 0.0261(9) -0.0003(7) 0.0095(8) -0.0013(7) C17 0.0341(10) 0.0378(10) 0.0280(9) 0.0011(7) 0.0073(8) -0.0027(8) C18 0.0387(10) 0.0354(10) 0.0323(10) -0.0083(8) 0.0140(8) -0.0141(8) C19 0.0363(10) 0.0261(9) 0.0436(11) -0.0075(8) 0.0192(9) -0.0075(7) C20 0.0311(9) 0.0275(9) 0.0359(10) -0.0020(7) 0.0117(8) -0.0022(7) C21 0.0284(9) 0.0167(7) 0.0260(9) -0.0036(6) 0.0066(7) -0.0008(6) C22 0.0259(9) 0.0255(8) 0.0262(8) -0.0031(7) 0.0038(7) 0.0010(6) C23 0.0327(10) 0.0315(9) 0.0275(9) -0.0028(7) 0.0078(8) -0.0007(7) C24 0.0309(9) 0.0291(9) 0.0382(10) -0.0035(7) 0.0143(8) -0.0038(7) C25 0.0252(9) 0.0290(9) 0.0408(11) -0.0030(8) 0.0053(8) 0.0012(7) C26 0.0302(9) 0.0235(8) 0.0286(9) -0.0015(7) 0.0031(7) 0.0010(6) N1 0.0329(8) 0.0280(7) 0.0264(7) 0.0014(6) 0.0033(6) 0.0017(6) O3 0.0433(8) 0.0252(7) 0.0444(8) -0.0041(5) 0.0041(6) -0.0039(5) O4 0.0471(8) 0.0301(7) 0.0268(7) 0.0013(5) -0.0004(6) 0.0054(5) C27 0.0345(9) 0.0266(9) 0.0221(8) 0.0004(7) 0.0004(7) 0.0000(7) C28 0.0410(10) 0.0274(9) 0.0249(9) -0.0015(7) 0.0007(8) 0.0030(7) C29 0.0427(11) 0.0385(10) 0.0237(9) 0.0006(7) 0.0067(8) 0.0088(8) C30 0.0390(11) 0.0461(11) 0.0246(9) 0.0088(8) 0.0069(8) -0.0004(8) C31 0.0442(11) 0.0316(10) 0.0331(10) 0.0051(8) 0.0062(8) -0.0045(8) C32 0.0403(10) 0.0255(9) 0.0273(9) 0.0022(7) 0.0057(8) 0.0007(7) C33 0.0363(10) 0.0249(9) 0.0230(8) 0.0001(7) -0.0008(7) -0.0021(7) C34 0.0307(9) 0.0215(8) 0.0275(9) 0.0008(7) 0.0015(7) -0.0050(7) C35 0.0368(10) 0.0315(9) 0.0282(9) 0.0024(7) 0.0022(8) 0.0032(7) C36 0.0365(10) 0.0388(10) 0.0308(9) -0.0001(8) 0.0010(8) 0.0017(8) C37 0.0468(12) 0.0375(10) 0.0330(10) -0.0060(8) 0.0040(9) 0.0005(8) C38 0.0437(11) 0.0322(9) 0.0347(10) -0.0010(8) 0.0093(9) 0.0046(8) C39 0.0317(10) 0.0346(9) 0.0307(9) 0.0031(7) 0.0080(8) 0.0055(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 C1 1.4421(19) . ? O1 H1 0.8400 . ? O2 C14 1.4426(19) . ? O2 H2 0.8400 . ? C1 C2 1.553(2) . ? C1 C8 1.563(2) . ? C1 C14 1.594(2) . ? C2 C3 1.399(2) . ? C2 C7 1.401(2) . ? C3 C4 1.397(2) . ? C3 H3 0.9500 . ? C4 C5 1.398(3) . ? C4 H4 0.9500 . ? C5 C6 1.386(3) . ? C5 H5 0.9500 . ? C6 C7 1.392(2) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C13 1.404(2) . ? C8 C9 1.406(2) . ? C9 C10 1.404(2) . ? C9 H9 0.9500 . ? C11 C10 1.393(2) . ? C11 C12 1.396(2) . ? C11 H11 0.9500 . ? C10 H10 0.9500 . ? C12 C13 1.409(2) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C21 1.547(2) . ? C14 C15 1.572(2) . ? C15 C20 1.409(2) . ? C15 C16 1.414(2) . ? C16 C17 1.417(2) . ? C16 H16 0.9500 . ? C17 C18 1.398(3) . ? C17 H17 0.9500 . ? C18 C19 1.408(3) . ? C18 H18 0.9500 . ? C19 C20 1.398(2) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 C22 1.408(2) . ? C21 C26 1.417(2) . ? C22 C23 1.387(2) . ? C22 H22 0.9500 . ? C23 C24 1.411(3) . ? C23 H23 0.9500 . ? C24 C25 1.390(3) . ? C24 H24 0.9500 . ? C25 C26 1.396(2) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? N1 C34 1.330(2) . ? N1 C39 1.484(2) . ? N1 C35 1.492(2) . ? O3 C33 1.2331(19) . ? O4 C34 1.252(2) . ? C27 C28 1.411(2) . ? C27 C32 1.413(2) . ? C27 C33 1.495(2) . ? C28 C29 1.387(3) . ? C28 H28 0.9500 . ? C29 C30 1.403(3) . ? C29 H29 0.9500 . ? C30 C31 1.397(3) . ? C30 H30 0.9500 . ? C31 C32 1.400(2) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? C33 C34 1.544(2) . ? C35 C36 1.542(2) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 C37 1.534(2) . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? C37 C38 1.542(3) . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? C38 C39 1.538(3) . ? C38 H38A 0.9900 . ? C38 H38B 0.9900 . ? C39 H39A 0.9900 . ? C39 H39B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1 109.5 . . ? C14 O2 H2 109.5 . . ? O1 C1 C2 107.72(12) . . ? O1 C1 C8 110.64(12) . . ? C2 C1 C8 109.38(12) . . ? O1 C1 C14 105.79(12) . . ? C2 C1 C14 114.31(12) . . ? C8 C1 C14 108.95(12) . . ? C3 C2 C7 118.34(15) . . ? C3 C2 C1 123.45(14) . . ? C7 C2 C1 118.07(13) . . ? C4 C3 C2 119.97(17) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 121.07(17) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? C6 C5 C4 119.08(16) . . ? C6 C5 H5 120.5 . . ? C4 C5 H5 120.5 . . ? C5 C6 C7 120.03(17) . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? C6 C7 C2 121.49(16) . . ? C6 C7 H7 119.3 . . ? C2 C7 H7 119.3 . . ? C13 C8 C9 117.15(15) . . ? C13 C8 C1 120.82(14) . . ? C9 C8 C1 122.02(14) . . ? C10 C9 C8 121.26(15) . . ? C10 C9 H9 119.4 . . ? C8 C9 H9 119.4 . . ? C10 C11 C12 118.48(16) . . ? C10 C11 H11 120.8 . . ? C12 C11 H11 120.8 . . ? C11 C10 C9 121.05(15) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C11 C12 C13 120.52(15) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C8 C13 C12 121.53(15) . . ? C8 C13 H13 119.2 . . ? C12 C13 H13 119.2 . . ? O2 C14 C21 110.41(13) . . ? O2 C14 C15 110.31(12) . . ? C21 C14 C15 107.45(12) . . ? O2 C14 C1 104.13(12) . . ? C21 C14 C1 110.43(12) . . ? C15 C14 C1 114.12(13) . . ? C20 C15 C16 117.94(15) . . ? C20 C15 C14 116.12(15) . . ? C16 C15 C14 125.85(14) . . ? C15 C16 C17 120.82(15) . . ? C15 C16 H16 119.6 . . ? C17 C16 H16 119.6 . . ? C18 C17 C16 120.20(17) . . ? C18 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C17 C18 C19 119.23(16) . . ? C17 C18 H18 120.4 . . ? C19 C18 H18 120.4 . . ? C20 C19 C18 120.51(16) . . ? C20 C19 H19 119.7 . . ? C18 C19 H19 119.7 . . ? C19 C20 C15 121.29(17) . . ? C19 C20 H20 119.4 . . ? C15 C20 H20 119.4 . . ? C22 C21 C26 118.72(14) . . ? C22 C21 C14 119.80(14) . . ? C26 C21 C14 121.46(14) . . ? C23 C22 C21 120.31(16) . . ? C23 C22 H22 119.8 . . ? C21 C22 H22 119.8 . . ? C22 C23 C24 120.34(16) . . ? C22 C23 H23 119.8 . . ? C24 C23 H23 119.8 . . ? C25 C24 C23 120.11(15) . . ? C25 C24 H24 119.9 . . ? C23 C24 H24 119.9 . . ? C24 C25 C26 119.70(16) . . ? C24 C25 H25 120.2 . . ? C26 C25 H25 120.2 . . ? C25 C26 C21 120.80(16) . . ? C25 C26 H26 119.6 . . ? C21 C26 H26 119.6 . . ? C34 N1 C39 121.61(14) . . ? C34 N1 C35 123.23(14) . . ? C39 N1 C35 115.11(13) . . ? C28 C27 C32 119.66(16) . . ? C28 C27 C33 118.84(15) . . ? C32 C27 C33 121.49(14) . . ? C29 C28 C27 120.16(16) . . ? C29 C28 H28 119.9 . . ? C27 C28 H28 119.9 . . ? C28 C29 C30 120.06(16) . . ? C28 C29 H29 120.0 . . ? C30 C29 H29 120.0 . . ? C31 C30 C29 120.39(17) . . ? C31 C30 H30 119.8 . . ? C29 C30 H30 119.8 . . ? C30 C31 C32 120.01(16) . . ? C30 C31 H31 120.0 . . ? C32 C31 H31 120.0 . . ? C31 C32 C27 119.72(16) . . ? C31 C32 H32 120.1 . . ? C27 C32 H32 120.1 . . ? O3 C33 C27 122.55(15) . . ? O3 C33 C34 118.74(15) . . ? C27 C33 C34 118.45(13) . . ? O4 C34 N1 126.26(15) . . ? O4 C34 C33 115.78(14) . . ? N1 C34 C33 117.94(14) . . ? N1 C35 C36 110.34(13) . . ? N1 C35 H35A 109.6 . . ? C36 C35 H35A 109.6 . . ? N1 C35 H35B 109.6 . . ? C36 C35 H35B 109.6 . . ? H35A C35 H35B 108.1 . . ? C37 C36 C35 110.06(15) . . ? C37 C36 H36A 109.6 . . ? C35 C36 H36A 109.6 . . ? C37 C36 H36B 109.6 . . ? C35 C36 H36B 109.6 . . ? H36A C36 H36B 108.2 . . ? C36 C37 C38 111.52(15) . . ? C36 C37 H37A 109.3 . . ? C38 C37 H37A 109.3 . . ? C36 C37 H37B 109.3 . . ? C38 C37 H37B 109.3 . . ? H37A C37 H37B 108.0 . . ? C39 C38 C37 112.04(14) . . ? C39 C38 H38A 109.2 . . ? C37 C38 H38A 109.2 . . ? C39 C38 H38B 109.2 . . ? C37 C38 H38B 109.2 . . ? H38A C38 H38B 107.9 . . ? N1 C39 C38 109.36(14) . . ? N1 C39 H39A 109.8 . . ? C38 C39 H39A 109.8 . . ? N1 C39 H39B 109.8 . . ? C38 C39 H39B 109.8 . . ? H39A C39 H39B 108.3 . . ? 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 O1 C1 C2 C3 149.22(16) . . . . ? C8 C1 C2 C3 -90.48(18) . . . . ? C14 C1 C2 C3 32.0(2) . . . . ? O1 C1 C2 C7 -35.02(18) . . . . ? C8 C1 C2 C7 85.28(17) . . . . ? C14 C1 C2 C7 -152.27(14) . . . . ? C7 C2 C3 C4 -0.7(3) . . . . ? C1 C2 C3 C4 175.09(17) . . . . ? C2 C3 C4 C5 -0.4(3) . . . . ? C3 C4 C5 C6 1.4(3) . . . . ? C4 C5 C6 C7 -1.4(3) . . . . ? C5 C6 C7 C2 0.4(3) . . . . ? C3 C2 C7 C6 0.6(3) . . . . ? C1 C2 C7 C6 -175.34(15) . . . . ? O1 C1 C8 C13 -30.77(19) . . . . ? C2 C1 C8 C13 -149.27(14) . . . . ? C14 C1 C8 C13 85.12(17) . . . . ? O1 C1 C8 C9 148.38(14) . . . . ? C2 C1 C8 C9 29.88(19) . . . . ? C14 C1 C8 C9 -95.72(16) . . . . ? C13 C8 C9 C10 0.8(2) . . . . ? C1 C8 C9 C10 -178.34(14) . . . . ? C12 C11 C10 C9 0.5(3) . . . . ? C8 C9 C10 C11 -0.7(3) . . . . ? C10 C11 C12 C13 -0.5(2) . . . . ? C9 C8 C13 C12 -0.8(2) . . . . ? C1 C8 C13 C12 178.37(13) . . . . ? C11 C12 C13 C8 0.7(2) . . . . ? O1 C1 C14 O2 172.21(12) . . . . ? C2 C1 C14 O2 -69.44(16) . . . . ? C8 C1 C14 O2 53.24(15) . . . . ? O1 C1 C14 C21 53.69(16) . . . . ? C2 C1 C14 C21 172.04(13) . . . . ? C8 C1 C14 C21 -65.28(16) . . . . ? O1 C1 C14 C15 -67.47(15) . . . . ? C2 C1 C14 C15 50.88(18) . . . . ? C8 C1 C14 C15 173.56(12) . . . . ? O2 C14 C15 C20 -52.59(17) . . . . ? C21 C14 C15 C20 67.82(17) . . . . ? C1 C14 C15 C20 -169.39(13) . . . . ? O2 C14 C15 C16 130.92(15) . . . . ? C21 C14 C15 C16 -108.68(17) . . . . ? C1 C14 C15 C16 14.1(2) . . . . ? C20 C15 C16 C17 0.6(2) . . . . ? C14 C15 C16 C17 177.04(14) . . . . ? C15 C16 C17 C18 -1.2(2) . . . . ? C16 C17 C18 C19 0.9(2) . . . . ? C17 C18 C19 C20 0.0(2) . . . . ? C18 C19 C20 C15 -0.6(2) . . . . ? C16 C15 C20 C19 0.3(2) . . . . ? C14 C15 C20 C19 -176.48(14) . . . . ? O2 C14 C21 C22 168.35(13) . . . . ? C15 C14 C21 C22 48.01(18) . . . . ? C1 C14 C21 C22 -77.03(18) . . . . ? O2 C14 C21 C26 -10.01(19) . . . . ? C15 C14 C21 C26 -130.35(15) . . . . ? C1 C14 C21 C26 104.60(16) . . . . ? C26 C21 C22 C23 -1.2(2) . . . . ? C14 C21 C22 C23 -179.65(14) . . . . ? C21 C22 C23 C24 1.6(2) . . . . ? C22 C23 C24 C25 -0.5(2) . . . . ? C23 C24 C25 C26 -0.9(2) . . . . ? C24 C25 C26 C21 1.3(2) . . . . ? C22 C21 C26 C25 -0.2(2) . . . . ? C14 C21 C26 C25 178.18(14) . . . . ? C32 C27 C28 C29 0.5(2) . . . . ? C33 C27 C28 C29 -179.70(15) . . . . ? C27 C28 C29 C30 -0.7(3) . . . . ? C28 C29 C30 C31 0.4(3) . . . . ? C29 C30 C31 C32 0.0(3) . . . . ? C30 C31 C32 C27 -0.2(3) . . . . ? C28 C27 C32 C31 0.0(2) . . . . ? C33 C27 C32 C31 -179.86(15) . . . . ? C28 C27 C33 O3 -3.6(2) . . . . ? C32 C27 C33 O3 176.21(16) . . . . ? C28 C27 C33 C34 170.37(15) . . . . ? C32 C27 C33 C34 -9.8(2) . . . . ? C39 N1 C34 O4 0.8(3) . . . . ? C35 N1 C34 O4 178.04(15) . . . . ? C39 N1 C34 C33 179.49(14) . . . . ? C35 N1 C34 C33 -3.3(2) . . . . ? O3 C33 C34 O4 91.73(19) . . . . ? C27 C33 C34 O4 -82.50(19) . . . . ? O3 C33 C34 N1 -87.11(19) . . . . ? C27 C33 C34 N1 98.65(18) . . . . ? C34 N1 C35 C36 -119.75(17) . . . . ? C39 N1 C35 C36 57.66(18) . . . . ? N1 C35 C36 C37 -54.71(18) . . . . ? C35 C36 C37 C38 54.2(2) . . . . ? C36 C37 C38 C39 -54.1(2) . . . . ? C34 N1 C39 C38 121.47(16) . . . . ? C35 N1 C39 C38 -55.99(18) . . . . ? C37 C38 C39 N1 52.94(19) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.211 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.038 # Attachment 'IIa.cif' data_IIa _database_code_depnum_ccdc_archive 'CCDC 666881' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,1,6,6-tetrahphenyl-2,4-hexadiyne-1,6-diol, 4-oxo(phenylacetyl)morpholine clathrate ; _chemical_name_common ; 1,1,6,6-tetrahphenyl-2,4-hexadiyne-1,6-diol, 4- oxo(phenylacetyl)morpholine clathrate ; _chemical_melting_point ? _chemical_formula_moiety 'C30 H22 O2, 2(C12 H13 N O3)' _chemical_formula_sum 'C54 H48 N2 O8' _chemical_formula_weight 852.94 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.9540(2) _cell_length_b 27.5070(7) _cell_length_c 13.7050(5) _cell_angle_alpha 90.00 _cell_angle_beta 94.7310(9) _cell_angle_gamma 90.00 _cell_volume 2236.91(12) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3145 _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 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.266 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 900 _exptl_absorpt_coefficient_mu 0.085 _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 ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3584 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0963 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3584 _reflns_number_gt 1599 _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^)+(0.0656P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.028(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3584 _refine_ls_number_parameters 291 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1456 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.1321 _refine_ls_wR_factor_gt 0.1076 _refine_ls_goodness_of_fit_ref 0.869 _refine_ls_restrained_S_all 0.869 _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 0.9432(2) 0.07442(7) 0.55597(12) 0.0693(5) Uani 1 1 d . . . H1 H 0.9373 0.0544 0.6000 0.104 Uiso 1 1 calc R . . C1 C 1.4343(4) 0.01974(11) 0.51163(18) 0.0635(7) Uani 1 1 d . . . C2 C 1.3194(4) 0.05310(11) 0.53256(18) 0.0615(7) Uani 1 1 d . . . C3 C 1.1670(4) 0.09317(9) 0.55676(17) 0.0576(7) Uani 1 1 d . . . C4 C 1.2369(4) 0.11553(9) 0.65729(17) 0.0573(7) Uani 1 1 d . . . C5 C 1.4523(4) 0.11071(10) 0.70331(18) 0.0700(8) Uani 1 1 d . . . H5 H 1.5601 0.0926 0.6740 0.084 Uiso 1 1 calc R . . C6 C 1.5066(5) 0.13297(11) 0.7931(2) 0.0817(9) Uani 1 1 d . . . H6 H 1.6501 0.1291 0.8243 0.098 Uiso 1 1 calc R . . C7 C 1.3515(5) 0.16046(11) 0.8357(2) 0.0838(9) Uani 1 1 d . . . H7 H 1.3904 0.1758 0.8951 0.101 Uiso 1 1 calc R . . C8 C 1.1376(5) 0.16544(11) 0.7909(2) 0.0847(9) Uani 1 1 d . . . H8 H 1.0306 0.1837 0.8206 0.102 Uiso 1 1 calc R . . C9 C 1.0821(4) 0.14324(10) 0.70159(19) 0.0715(8) Uani 1 1 d . . . H9 H 0.9379 0.1471 0.6710 0.086 Uiso 1 1 calc R . . C10 C 1.1633(4) 0.13240(10) 0.47777(17) 0.0629(7) Uani 1 1 d . . . C11 C 1.3553(5) 0.15819(13) 0.4641(2) 0.0978(10) Uani 1 1 d . . . H11 H 1.4872 0.1513 0.5028 0.117 Uiso 1 1 calc R . . C12 C 1.3564(7) 0.19415(15) 0.3940(3) 0.1215(13) Uani 1 1 d . . . H12 H 1.4879 0.2115 0.3867 0.146 Uiso 1 1 calc R . . C13 C 1.1692(9) 0.20430(14) 0.3362(3) 0.1122(12) Uani 1 1 d . . . H13 H 1.1714 0.2283 0.2886 0.135 Uiso 1 1 calc R . . C14 C 0.9757(7) 0.17917(15) 0.3477(3) 0.1097(12) Uani 1 1 d . . . H14 H 0.8462 0.1860 0.3074 0.132 Uiso 1 1 calc R . . C15 C 0.9705(5) 0.14309(11) 0.4196(2) 0.0865(9) Uani 1 1 d . . . H15 H 0.8374 0.1265 0.4279 0.104 Uiso 1 1 calc R . . N1 N 0.7282(4) 0.02817(9) 0.14681(16) 0.0770(7) Uani 1 1 d . . . O2 O 0.3281(4) 0.09732(9) 0.12100(18) 0.1234(9) Uani 1 1 d . . . O3 O 0.6787(3) 0.05130(8) -0.01276(16) 0.1021(7) Uani 1 1 d . . . O4 O 1.0422(3) -0.01153(8) 0.28866(13) 0.0878(6) Uani 1 1 d . . . C16 C 0.5215(6) 0.10257(14) 0.1004(2) 0.0836(9) Uani 1 1 d . . . C17 C 0.6224(5) 0.15108(14) 0.09162(19) 0.0759(8) Uani 1 1 d . . . C18 C 0.5100(6) 0.19075(18) 0.1243(2) 0.0990(11) Uani 1 1 d . . . H18 H 0.3733 0.1863 0.1513 0.119 Uiso 1 1 calc R . . C19 C 0.5959(9) 0.23651(19) 0.1177(3) 0.1279(14) Uani 1 1 d . . . H19 H 0.5191 0.2630 0.1408 0.153 Uiso 1 1 calc R . . C20 C 0.7974(9) 0.24311(16) 0.0766(3) 0.1253(14) Uani 1 1 d . . . H20 H 0.8555 0.2743 0.0709 0.150 Uiso 1 1 calc R . . C21 C 0.9122(6) 0.20404(19) 0.0441(2) 0.1073(12) Uani 1 1 d . . . H21 H 1.0477 0.2087 0.0161 0.129 Uiso 1 1 calc R . . C22 C 0.8270(6) 0.15788(15) 0.0529(2) 0.0897(9) Uani 1 1 d . . . H22 H 0.9074 0.1312 0.0328 0.108 Uiso 1 1 calc R . . C23 C 0.6543(5) 0.05804(12) 0.0737(3) 0.0793(8) Uani 1 1 d . . . C24 C 0.7124(5) 0.03790(11) 0.25103(19) 0.0856(9) Uani 1 1 d . . . H24A H 0.6124 0.0145 0.2778 0.103 Uiso 1 1 calc R . . H24B H 0.6508 0.0701 0.2594 0.103 Uiso 1 1 calc R . . C25 C 0.9430(5) 0.03448(12) 0.3045(2) 0.0866(9) Uani 1 1 d . . . H25A H 1.0384 0.0600 0.2817 0.104 Uiso 1 1 calc R . . H25B H 0.9314 0.0392 0.3740 0.104 Uiso 1 1 calc R . . C26 C 1.0667(5) -0.01875(11) 0.1870(2) 0.0869(9) Uani 1 1 d . . . H26A H 1.1374 -0.0500 0.1777 0.104 Uiso 1 1 calc R . . H26B H 1.1642 0.0063 0.1639 0.104 Uiso 1 1 calc R . . C27 C 0.8435(5) -0.01711(11) 0.12814(19) 0.0811(9) Uani 1 1 d . . . H27A H 0.8658 -0.0196 0.0590 0.097 Uiso 1 1 calc R . . H27B H 0.7518 -0.0444 0.1456 0.097 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 0.0628(10) 0.0677(15) 0.0764(13) -0.0020(9) 0.0003(8) -0.0052(9) C1 0.0684(18) 0.060(2) 0.0616(17) -0.0032(16) 0.0008(13) 0.0002(15) C2 0.0677(16) 0.056(2) 0.0598(16) -0.0016(14) 0.0018(13) -0.0024(16) C3 0.0601(16) 0.0530(19) 0.0591(16) -0.0070(14) 0.0011(12) 0.0033(14) C4 0.0632(15) 0.0532(19) 0.0553(15) -0.0031(13) 0.0029(13) 0.0025(13) C5 0.0706(17) 0.070(2) 0.0684(18) -0.0087(15) -0.0015(14) 0.0052(14) C6 0.0824(19) 0.084(3) 0.075(2) -0.0129(17) -0.0157(16) 0.0073(17) C7 0.100(2) 0.082(3) 0.0670(19) -0.0169(16) -0.0046(18) 0.0026(18) C8 0.088(2) 0.084(3) 0.082(2) -0.0208(18) 0.0089(17) 0.0116(17) C9 0.0708(17) 0.069(2) 0.0742(19) -0.0094(16) 0.0015(14) 0.0092(15) C10 0.0777(18) 0.057(2) 0.0532(16) -0.0064(14) 0.0021(14) 0.0077(16) C11 0.099(2) 0.104(3) 0.090(2) 0.026(2) 0.0019(18) -0.014(2) C12 0.136(3) 0.117(4) 0.113(3) 0.038(3) 0.018(3) -0.016(2) C13 0.172(4) 0.078(3) 0.089(3) 0.013(2) 0.024(3) 0.021(3) C14 0.143(3) 0.095(3) 0.088(3) 0.011(2) -0.011(2) 0.039(3) C15 0.102(2) 0.074(3) 0.081(2) 0.0039(18) -0.0065(18) 0.0190(17) N1 0.0952(15) 0.071(2) 0.0643(16) 0.0039(14) 0.0034(12) 0.0089(14) O2 0.0906(15) 0.118(2) 0.164(2) 0.0296(16) 0.0273(14) 0.0081(14) O3 0.1378(16) 0.1035(19) 0.0644(13) 0.0051(13) 0.0043(12) 0.0116(13) O4 0.1156(14) 0.0784(17) 0.0680(14) 0.0035(11) -0.0013(10) 0.0098(13) C16 0.088(2) 0.089(3) 0.073(2) 0.0154(18) 0.0019(16) 0.010(2) C17 0.082(2) 0.081(3) 0.0638(18) 0.0054(18) -0.0008(15) 0.009(2) C18 0.120(3) 0.097(3) 0.079(2) 0.010(2) 0.0053(19) 0.023(3) C19 0.175(4) 0.101(4) 0.108(3) -0.006(3) 0.010(3) 0.028(3) C20 0.182(4) 0.086(4) 0.104(3) 0.002(3) -0.014(3) -0.018(3) C21 0.114(3) 0.110(4) 0.097(3) 0.001(3) 0.002(2) -0.021(3) C22 0.090(2) 0.091(3) 0.086(2) 0.0009(19) -0.0014(17) 0.003(2) C23 0.0882(19) 0.073(3) 0.076(2) 0.011(2) 0.0031(17) -0.0021(18) C24 0.106(2) 0.086(3) 0.066(2) 0.0000(16) 0.0140(16) 0.0041(17) C25 0.113(2) 0.077(3) 0.0682(19) -0.0047(17) -0.0009(17) -0.0010(19) C26 0.108(2) 0.078(3) 0.075(2) 0.0002(17) 0.0082(17) 0.0145(18) C27 0.112(2) 0.066(2) 0.0657(18) 0.0006(16) 0.0067(16) -0.0035(19) _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 1.428(2) . ? O1 H1 0.8200 . ? C1 C2 1.194(3) . ? C1 C1 1.391(6) 3_856 ? C2 C3 1.482(4) . ? C3 C10 1.527(3) . ? C3 C4 1.535(3) . ? C4 C9 1.375(3) . ? C4 C5 1.388(3) . ? C5 C6 1.388(3) . ? C5 H5 0.9300 . ? C6 C7 1.362(4) . ? C6 H6 0.9300 . ? C7 C8 1.374(3) . ? C7 H7 0.9300 . ? C8 C9 1.384(3) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.371(4) . ? C10 C15 1.374(3) . ? C11 C12 1.380(4) . ? C11 H11 0.9300 . ? C12 C13 1.342(5) . ? C12 H12 0.9300 . ? C13 C14 1.363(5) . ? C13 H13 0.9300 . ? C14 C15 1.401(4) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? N1 C23 1.341(3) . ? N1 C27 1.455(3) . ? N1 C24 1.464(3) . ? O2 C16 1.217(3) . ? O3 C23 1.220(3) . ? O4 C25 1.421(3) . ? O4 C26 1.427(3) . ? C16 C17 1.472(4) . ? C16 C23 1.519(4) . ? C17 C18 1.374(4) . ? C17 C22 1.381(4) . ? C18 C19 1.364(5) . ? C18 H18 0.9300 . ? C19 C20 1.379(5) . ? C19 H19 0.9300 . ? C20 C21 1.368(5) . ? C20 H20 0.9300 . ? C21 C22 1.376(4) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C24 C25 1.505(3) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 C27 1.498(3) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? 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 178.9(4) . 3_856 ? C1 C2 C3 177.2(3) . . ? O1 C3 C2 108.5(2) . . ? O1 C3 C10 106.92(18) . . ? C2 C3 C10 109.87(19) . . ? O1 C3 C4 109.61(19) . . ? C2 C3 C4 111.90(19) . . ? C10 C3 C4 109.9(2) . . ? C9 C4 C5 118.7(2) . . ? C9 C4 C3 118.4(2) . . ? C5 C4 C3 122.8(2) . . ? C4 C5 C6 120.0(2) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C7 C6 C5 120.6(2) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C6 C7 C8 120.0(3) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C7 C8 C9 119.7(3) . . ? C7 C8 H8 120.1 . . ? C9 C8 H8 120.1 . . ? C4 C9 C8 121.0(2) . . ? C4 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C11 C10 C15 118.4(3) . . ? C11 C10 C3 119.9(2) . . ? C15 C10 C3 121.6(3) . . ? C10 C11 C12 121.2(3) . . ? C10 C11 H11 119.4 . . ? C12 C11 H11 119.4 . . ? C13 C12 C11 120.6(4) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C12 C13 C14 119.7(4) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? C13 C14 C15 120.5(3) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C10 C15 C14 119.6(3) . . ? C10 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? C23 N1 C27 121.6(2) . . ? C23 N1 C24 125.0(3) . . ? C27 N1 C24 113.4(2) . . ? C25 O4 C26 110.5(2) . . ? O2 C16 C17 121.8(3) . . ? O2 C16 C23 118.8(3) . . ? C17 C16 C23 119.2(3) . . ? C18 C17 C22 119.1(3) . . ? C18 C17 C16 118.7(4) . . ? C22 C17 C16 122.2(4) . . ? C19 C18 C17 121.1(4) . . ? C19 C18 H18 119.5 . . ? C17 C18 H18 119.5 . . ? C18 C19 C20 119.4(4) . . ? C18 C19 H19 120.3 . . ? C20 C19 H19 120.3 . . ? C21 C20 C19 120.3(4) . . ? C21 C20 H20 119.8 . . ? C19 C20 H20 119.8 . . ? C20 C21 C22 119.9(4) . . ? C20 C21 H21 120.0 . . ? C22 C21 H21 120.0 . . ? C21 C22 C17 120.1(3) . . ? C21 C22 H22 119.9 . . ? C17 C22 H22 119.9 . . ? O3 C23 N1 125.0(3) . . ? O3 C23 C16 117.5(3) . . ? N1 C23 C16 117.4(3) . . ? N1 C24 C25 109.5(2) . . ? N1 C24 H24A 109.8 . . ? C25 C24 H24A 109.8 . . ? N1 C24 H24B 109.8 . . ? C25 C24 H24B 109.8 . . ? H24A C24 H24B 108.2 . . ? O4 C25 C24 110.8(2) . . ? O4 C25 H25A 109.5 . . ? C24 C25 H25A 109.5 . . ? O4 C25 H25B 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 108.1 . . ? O4 C26 C27 111.3(2) . . ? O4 C26 H26A 109.4 . . ? C27 C26 H26A 109.4 . . ? O4 C26 H26B 109.4 . . ? C27 C26 H26B 109.4 . . ? H26A C26 H26B 108.0 . . ? N1 C27 C26 110.0(2) . . ? N1 C27 H27A 109.7 . . ? C26 C27 H27A 109.7 . . ? N1 C27 H27B 109.7 . . ? C26 C27 H27B 109.7 . . ? H27A C27 H27B 108.2 . . ? 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 -55(21) 3_856 . . . ? C1 C2 C3 O1 16(6) . . . . ? C1 C2 C3 C10 -100(6) . . . . ? C1 C2 C3 C4 137(6) . . . . ? O1 C3 C4 C9 -42.0(3) . . . . ? C2 C3 C4 C9 -162.5(2) . . . . ? C10 C3 C4 C9 75.2(3) . . . . ? O1 C3 C4 C5 140.8(2) . . . . ? C2 C3 C4 C5 20.4(3) . . . . ? C10 C3 C4 C5 -102.0(3) . . . . ? C9 C4 C5 C6 1.0(4) . . . . ? C3 C4 C5 C6 178.2(2) . . . . ? C4 C5 C6 C7 -1.4(4) . . . . ? C5 C6 C7 C8 1.5(5) . . . . ? C6 C7 C8 C9 -1.3(5) . . . . ? C5 C4 C9 C8 -0.9(4) . . . . ? C3 C4 C9 C8 -178.2(2) . . . . ? C7 C8 C9 C4 1.0(4) . . . . ? O1 C3 C10 C11 177.7(2) . . . . ? C2 C3 C10 C11 -64.7(3) . . . . ? C4 C3 C10 C11 58.8(3) . . . . ? O1 C3 C10 C15 -1.8(3) . . . . ? C2 C3 C10 C15 115.8(2) . . . . ? C4 C3 C10 C15 -120.7(3) . . . . ? C15 C10 C11 C12 0.2(5) . . . . ? C3 C10 C11 C12 -179.3(3) . . . . ? C10 C11 C12 C13 -1.0(6) . . . . ? C11 C12 C13 C14 0.7(6) . . . . ? C12 C13 C14 C15 0.4(6) . . . . ? C11 C10 C15 C14 0.9(4) . . . . ? C3 C10 C15 C14 -179.6(3) . . . . ? C13 C14 C15 C10 -1.2(5) . . . . ? O2 C16 C17 C18 11.7(4) . . . . ? C23 C16 C17 C18 -174.1(3) . . . . ? O2 C16 C17 C22 -169.1(3) . . . . ? C23 C16 C17 C22 5.0(4) . . . . ? C22 C17 C18 C19 0.9(4) . . . . ? C16 C17 C18 C19 -179.9(3) . . . . ? C17 C18 C19 C20 0.8(5) . . . . ? C18 C19 C20 C21 -1.1(6) . . . . ? C19 C20 C21 C22 -0.3(5) . . . . ? C20 C21 C22 C17 2.0(5) . . . . ? C18 C17 C22 C21 -2.3(4) . . . . ? C16 C17 C22 C21 178.5(3) . . . . ? C27 N1 C23 O3 -1.5(4) . . . . ? C24 N1 C23 O3 175.6(3) . . . . ? C27 N1 C23 C16 175.8(2) . . . . ? C24 N1 C23 C16 -7.1(4) . . . . ? O2 C16 C23 O3 103.1(3) . . . . ? C17 C16 C23 O3 -71.2(4) . . . . ? O2 C16 C23 N1 -74.4(4) . . . . ? C17 C16 C23 N1 111.3(3) . . . . ? C23 N1 C24 C25 -124.7(3) . . . . ? C27 N1 C24 C25 52.6(3) . . . . ? C26 O4 C25 C24 60.7(3) . . . . ? N1 C24 C25 O4 -56.1(3) . . . . ? C25 O4 C26 C27 -60.2(3) . . . . ? C23 N1 C27 C26 125.4(3) . . . . ? C24 N1 C27 C26 -52.1(3) . . . . ? O4 C26 C27 N1 54.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.99 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.99 _refine_diff_density_max 0.142 _refine_diff_density_min -0.130 _refine_diff_density_rms 0.032 # Attachment 'Ib.cif' data_Ib _database_code_depnum_ccdc_archive 'CCDC 666883' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4,5-bis(hydroxydiphenylmethyl)-2,2-dimethyl-1,3- dioxolane, 1-(phenylglyoxylyl)piperidine clathrate ; _chemical_name_common ; 4,5-bis(hydroxydiphenylmethyl)-2,2-dimethyl-1,3-dioxolane, 1- (phenylglyoxylyl)piperidine clathrate ; _chemical_melting_point ? _chemical_formula_moiety 'C34 H34 O4, C13 H15 N O2' _chemical_formula_sum 'C47 H49 N O6' _chemical_formula_weight 723.87 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 monoclinic _symmetry_space_group_name_H-M P21 _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.4158(2) _cell_length_b 40.9669(10) _cell_length_c 10.2490(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.7547(16) _cell_angle_gamma 90.00 _cell_volume 3951.56(17) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _chemical_absolute_configuration unk _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.217 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1544 _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 ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11479 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.2029 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -48 _diffrn_reflns_limit_k_max 44 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 25.01 _reflns_number_total 11479 _reflns_number_gt 4482 _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^)+(0.0851P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_number_reflns 6752 _refine_ls_number_parameters 935 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1436 _refine_ls_R_factor_gt 0.0527 _refine_ls_wR_factor_ref 0.1543 _refine_ls_wR_factor_gt 0.1180 _refine_ls_goodness_of_fit_ref 0.773 _refine_ls_restrained_S_all 0.773 _refine_ls_shift/su_max 0.034 _refine_ls_shift/su_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1A O 0.9620(6) 0.56423(13) 0.6116(4) 0.0659(15) Uani 1 1 d . . . H1OA H 1.0161 0.5560 0.6667 0.099 Uiso 1 1 calc R . . O2A O 1.1233(6) 0.53962(12) 0.8015(4) 0.0617(14) Uani 1 1 d . . . H2OA H 1.1648 0.5221 0.8112 0.093 Uiso 1 1 calc R . . O3A O 0.8442(5) 0.61843(11) 0.8747(4) 0.0473(12) Uani 1 1 d . . . O4A O 1.0482(5) 0.60922(11) 0.9946(4) 0.0487(12) Uani 1 1 d . . . C1A C 0.9113(7) 0.59008(18) 0.8196(6) 0.0483(18) Uani 1 1 d . . . H1A H 0.8691 0.5701 0.8481 0.058 Uiso 1 1 d R . . C2A C 0.8929(8) 0.59265(19) 0.6672(6) 0.0522(19) Uani 1 1 d . . . C3A C 0.9566(8) 0.6235(2) 0.6150(6) 0.052(2) Uani 1 1 d . . . C4A C 0.8857(9) 0.6527(2) 0.6172(7) 0.060(2) Uani 1 1 d . . . H4A H 0.7907 0.6528 0.6487 0.072 Uiso 1 1 d R . . C5A C 0.9472(12) 0.6812(3) 0.5747(8) 0.087(3) Uani 1 1 d . . . H5A H 0.8943 0.7013 0.5753 0.104 Uiso 1 1 d R . . C6A C 1.0840(13) 0.6800(3) 0.5272(10) 0.099(4) Uani 1 1 d . . . H6A H 1.1322 0.6997 0.5034 0.119 Uiso 1 1 d R . . C7A C 1.1522(12) 0.6521(4) 0.5218(9) 0.110(4) Uani 1 1 d . . . H7A H 1.2441 0.6521 0.4838 0.132 Uiso 1 1 d R . . C8A C 1.0937(9) 0.6237(3) 0.5633(7) 0.075(3) Uani 1 1 d . . . H8A H 1.1434 0.6032 0.5612 0.090 Uiso 1 1 d R . . C9A C 0.7376(8) 0.58915(17) 0.6190(7) 0.0476(18) Uani 1 1 d . . . C10A C 0.6219(9) 0.58676(19) 0.6978(7) 0.061(2) Uani 1 1 d . . . H10A H 0.6365 0.5879 0.7908 0.073 Uiso 1 1 d R . . C11A C 0.4840(8) 0.5827(2) 0.6432(9) 0.074(3) Uani 1 1 d . . . H11A H 0.4059 0.5811 0.7008 0.089 Uiso 1 1 d R . . C12A C 0.4618(9) 0.58083(18) 0.5120(9) 0.064(2) Uani 1 1 d . . . H12A H 0.3686 0.5780 0.4730 0.077 Uiso 1 1 d R . . C13A C 0.5764(10) 0.5836(2) 0.4312(7) 0.070(2) Uani 1 1 d . . . H13A H 0.5647 0.5816 0.3382 0.084 Uiso 1 1 d R . . C14A C 0.7146(9) 0.58830(19) 0.4842(7) 0.059(2) Uani 1 1 d . . . H14A H 0.7947 0.5919 0.4302 0.071 Uiso 1 1 d R . . C15A C 1.0618(7) 0.59059(16) 0.8808(6) 0.0426(17) Uani 1 1 d . . . H15A H 1.1230 0.6000 0.8177 0.051 Uiso 1 1 d R . . C16A C 1.1281(7) 0.55725(18) 0.9223(6) 0.0501(19) Uani 1 1 d . . . C17A C 1.0359(8) 0.54028(19) 1.0266(8) 0.056(2) Uani 1 1 d . . . C18A C 1.0429(9) 0.55106(19) 1.1532(8) 0.065(2) Uani 1 1 d . . . H18A H 1.1046 0.5690 1.1746 0.078 Uiso 1 1 d R . . C19A C 0.9549(11) 0.5362(3) 1.2440(9) 0.094(3) Uani 1 1 d . . . H19A H 0.9552 0.5434 1.3331 0.113 Uiso 1 1 d R . . C20A C 0.8659(13) 0.5094(4) 1.2004(17) 0.119(5) Uani 1 1 d . . . H20A H 0.8073 0.4990 1.2630 0.142 Uiso 1 1 d R . . C21A C 0.8676(12) 0.4999(3) 1.0824(16) 0.101(4) Uani 1 1 d . . . H21A H 0.8086 0.4821 1.0525 0.122 Uiso 1 1 d R . . C22A C 0.9505(9) 0.5145(2) 0.9952(10) 0.074(3) Uani 1 1 d . . . H22A H 0.9517 0.5066 0.9070 0.089 Uiso 1 1 d R . . C23A C 1.2806(7) 0.56007(19) 0.9726(6) 0.0504(19) Uani 1 1 d . . . C24A C 1.3595(9) 0.5310(2) 0.9888(7) 0.065(2) Uani 1 1 d . . . H24A H 1.3133 0.5105 0.9700 0.078 Uiso 1 1 d R . . C25A C 1.4996(10) 0.5321(3) 1.0299(8) 0.077(3) Uani 1 1 d . . . H25A H 1.5525 0.5122 1.0418 0.093 Uiso 1 1 d R . . C26A C 1.5656(9) 0.5616(3) 1.0553(8) 0.073(2) Uani 1 1 d . . . H26A H 1.6641 0.5621 1.0826 0.088 Uiso 1 1 d R . . C27A C 1.4927(9) 0.5903(2) 1.0400(7) 0.067(2) Uani 1 1 d . . . H27A H 1.5386 0.6108 1.0582 0.081 Uiso 1 1 d R . . C28A C 1.3489(8) 0.5891(2) 0.9982(6) 0.0534(19) Uani 1 1 d . . . H28A H 1.2979 0.6093 0.9868 0.064 Uiso 1 1 d R . . C29A C 0.9339(8) 0.63229(17) 0.9759(6) 0.0466(18) Uani 1 1 d . . . C30A C 0.8541(8) 0.63342(18) 1.0999(6) 0.057(2) Uani 1 1 d . . . H30C H 0.8286 0.6116 1.1237 0.068 Uiso 1 1 d R . . H30D H 0.7695 0.6461 1.0849 0.068 Uiso 1 1 d R . . C31A C 0.9426(9) 0.6500(2) 1.2112(7) 0.062(2) Uani 1 1 d . . . H31C H 1.0260 0.6369 1.2261 0.075 Uiso 1 1 d R . . H31D H 0.8906 0.6514 1.2901 0.075 Uiso 1 1 d R . . C32A C 0.9944(9) 0.6831(2) 1.1714(8) 0.072(2) Uani 1 1 d . . . H32C H 1.0508 0.6929 1.2405 0.086 Uiso 1 1 d R . . H32D H 0.9112 0.6961 1.1541 0.086 Uiso 1 1 d R . . C33A C 1.0776(8) 0.68136(19) 1.0463(7) 0.064(2) Uani 1 1 d . . . H33C H 1.1050 0.7028 1.0194 0.077 Uiso 1 1 d R . . H33D H 1.1611 0.6684 1.0639 0.077 Uiso 1 1 d R . . C34A C 0.9909(7) 0.66506(17) 0.9360(7) 0.0507(19) Uani 1 1 d . . . H34C H 0.9127 0.6792 0.9133 0.061 Uiso 1 1 d R . . H34D H 1.0485 0.6620 0.8613 0.061 Uiso 1 1 d R . . O5A O 0.9181(8) 0.91259(17) 0.3249(6) 0.107(2) Uani 1 1 d . . . O6A O 0.7850(7) 0.97933(14) 0.2553(6) 0.090(2) Uani 1 1 d . . . N1A N 0.8074(10) 0.9750(2) 0.4734(9) 0.108(3) Uani 1 1 d . . . C35A C 1.0967(11) 0.9525(2) 0.3142(8) 0.070(2) Uani 1 1 d . . . C36A C 1.1936(14) 0.9318(3) 0.2587(9) 0.099(3) Uani 1 1 d . . . H36A H 1.1604 0.9105 0.2341 0.119 Uiso 1 1 d R . . C37A C 1.3305(17) 0.9399(4) 0.2401(11) 0.119(4) Uani 1 1 d . . . H37A H 1.3937 0.9241 0.2045 0.143 Uiso 1 1 d R . . C38A C 1.3743(16) 0.9712(5) 0.2728(14) 0.136(5) Uani 1 1 d . . . H38A H 1.4704 0.9774 0.2557 0.163 Uiso 1 1 d R . . C39A C 1.2848(15) 0.9932(3) 0.3281(13) 0.122(5) Uani 1 1 d . . . H39A H 1.3179 1.0147 0.3506 0.146 Uiso 1 1 d R . . C40A C 1.1434(13) 0.9841(2) 0.3517(9) 0.097(3) Uani 1 1 d . . . H40A H 1.0784 0.9987 0.3922 0.116 Uiso 1 1 d R . . C41A C 0.9546(13) 0.9410(3) 0.3347(9) 0.088(3) Uani 1 1 d . . . C42A C 0.8372(11) 0.9668(2) 0.3522(11) 0.079(3) Uani 1 1 d . . . C43A C 0.8718(13) 0.9584(3) 0.5944(12) 0.128(4) Uani 1 1 d . . . H43C H 0.9302 0.9738 0.6420 0.154 Uiso 1 1 d R . . H43D H 0.9294 0.9405 0.5663 0.154 Uiso 1 1 d R . . C44A C 0.7718(15) 0.9471(3) 0.6804(12) 0.148(5) Uani 1 1 d . . . H44C H 0.8150 0.9365 0.7550 0.178 Uiso 1 1 d R . . H44D H 0.7131 0.9318 0.6326 0.178 Uiso 1 1 d R . . C45A C 0.6743(18) 0.9746(4) 0.7163(13) 0.179(7) Uani 1 1 d . . . H45C H 0.6062 0.9687 0.7800 0.214 Uiso 1 1 d R . . H45D H 0.7358 0.9913 0.7515 0.214 Uiso 1 1 d R . . C46A C 0.6052(14) 0.9892(3) 0.5906(16) 0.164(6) Uani 1 1 d . . . H46C H 0.5407 1.0063 0.6139 0.197 Uiso 1 1 d R . . H46D H 0.5529 0.9717 0.5494 0.197 Uiso 1 1 d R . . C47A C 0.7066(15) 1.0003(3) 0.5041(13) 0.147(5) Uani 1 1 d . . . H47C H 0.6648 1.0083 0.4237 0.177 Uiso 1 1 d R . . H47D H 0.7581 1.0175 0.5476 0.177 Uiso 1 1 d R . . O1B O 0.3646(6) 0.81711(11) 0.0612(4) 0.0608(14) Uani 1 1 d . . . H1OB H 0.3550 0.8367 0.0740 0.091 Uiso 1 1 calc R . . O2B O 0.5128(5) 0.79124(12) -0.1279(4) 0.0602(14) Uani 1 1 d . . . H2OB H 0.4732 0.8018 -0.0718 0.090 Uiso 1 1 calc R . . O3B O 0.4492(5) 0.74660(11) 0.2554(4) 0.0506(13) Uani 1 1 d . . . O4B O 0.6526(4) 0.74074(11) 0.1442(4) 0.0484(12) Uani 1 1 d . . . C1B C 0.4284(7) 0.76630(15) 0.1427(6) 0.0445(17) Uani 1 1 d . . . H1B H 0.3610 0.7574 0.0803 0.053 Uiso 1 1 d R . . C2B C 0.3688(7) 0.80001(16) 0.1850(7) 0.0471(18) Uani 1 1 d . . . C3B C 0.2172(8) 0.79783(19) 0.2315(6) 0.0488(18) Uani 1 1 d . . . C4B C 0.1513(8) 0.7686(2) 0.2676(7) 0.062(2) Uani 1 1 d . . . H4B H 0.2029 0.7485 0.2604 0.075 Uiso 1 1 d R . . C5B C 0.0123(8) 0.7691(2) 0.3105(7) 0.064(2) Uani 1 1 d . . . H5B H -0.0296 0.7490 0.3381 0.077 Uiso 1 1 d R . . C6B C -0.0625(8) 0.7971(2) 0.3166(7) 0.068(2) Uani 1 1 d . . . H6B H -0.1592 0.7972 0.3436 0.081 Uiso 1 1 d R . . C7B C 0.0003(9) 0.8262(2) 0.2833(7) 0.070(2) Uani 1 1 d . . . H7B H -0.0517 0.8463 0.2891 0.084 Uiso 1 1 d R . . C8B C 0.1393(8) 0.8259(2) 0.2423(7) 0.063(2) Uani 1 1 d . . . H8B H 0.1833 0.8462 0.2200 0.075 Uiso 1 1 d R . . C9B C 0.4653(8) 0.81754(18) 0.2860(8) 0.052(2) Uani 1 1 d . . . C10B C 0.4653(9) 0.80679(19) 0.4158(8) 0.066(2) Uani 1 1 d . . . H10B H 0.4040 0.7893 0.4407 0.080 Uiso 1 1 d R . . C11B C 0.5511(14) 0.8219(3) 0.5079(11) 0.105(4) Uani 1 1 d . . . H11B H 0.5470 0.8149 0.5972 0.126 Uiso 1 1 d R . . C12B C 0.6397(15) 0.8465(4) 0.4785(16) 0.127(6) Uani 1 1 d . . . H12B H 0.7023 0.8548 0.5464 0.152 Uiso 1 1 d R . . C13B C 0.6352(11) 0.8580(3) 0.3533(17) 0.122(5) Uani 1 1 d . . . H13B H 0.6933 0.8764 0.3317 0.146 Uiso 1 1 d R . . C14B C 0.5512(9) 0.8434(2) 0.2538(9) 0.080(3) Uani 1 1 d . . . H14B H 0.5473 0.8503 0.1643 0.096 Uiso 1 1 d R . . C15B C 0.5805(7) 0.76752(16) 0.0830(6) 0.0417(17) Uani 1 1 d . . . H15B H 0.6221 0.7881 0.1069 0.050 Uiso 1 1 d R . . C16B C 0.5873(7) 0.76437(17) -0.0681(6) 0.0446(18) Uani 1 1 d . . . C17B C 0.5221(8) 0.73266(18) -0.1199(6) 0.0478(19) Uani 1 1 d . . . C18B C 0.6008(9) 0.7037(2) -0.1165(6) 0.054(2) Uani 1 1 d . . . H18B H 0.6981 0.7046 -0.0859 0.065 Uiso 1 1 d R . . C19B C 0.5386(11) 0.6749(2) -0.1581(8) 0.069(2) Uani 1 1 d . . . H19B H 0.5921 0.6550 -0.1520 0.083 Uiso 1 1 d R . . C20B C 0.4016(14) 0.6742(3) -0.2067(8) 0.089(3) Uani 1 1 d . . . H20B H 0.3627 0.6539 -0.2377 0.106 Uiso 1 1 d R . . C21B C 0.3218(10) 0.7025(3) -0.2103(9) 0.086(3) Uani 1 1 d . . . H21B H 0.2257 0.7023 -0.2446 0.103 Uiso 1 1 d R . . C22B C 0.3827(9) 0.7311(2) -0.1665(7) 0.063(2) Uani 1 1 d . . . H22B H 0.3277 0.7508 -0.1667 0.076 Uiso 1 1 d R . . C23B C 0.7400(8) 0.76778(17) -0.1152(7) 0.0467(18) Uani 1 1 d . . . C24B C 0.7563(8) 0.76878(19) -0.2508(7) 0.061(2) Uani 1 1 d . . . H24B H 0.6728 0.7672 -0.3065 0.073 Uiso 1 1 d R . . C25B C 0.8892(10) 0.7719(2) -0.3034(8) 0.075(3) Uani 1 1 d . . . H25B H 0.9019 0.7717 -0.3960 0.090 Uiso 1 1 d R . . C26B C 1.0077(11) 0.7751(2) -0.2242(9) 0.082(3) Uani 1 1 d . . . H26B H 1.0986 0.7790 -0.2612 0.099 Uiso 1 1 d R . . C27B C 0.9932(9) 0.7739(2) -0.0897(9) 0.075(2) Uani 1 1 d . . . H27B H 1.0771 0.7740 -0.0340 0.090 Uiso 1 1 d R . . C28B C 0.8587(9) 0.7704(2) -0.0362(8) 0.066(2) Uani 1 1 d . . . H28B H 0.8470 0.7709 0.0565 0.079 Uiso 1 1 d R . . C29B C 0.5686(7) 0.72595(16) 0.2419(6) 0.0428(18) Uani 1 1 d . . . C30B C 0.5226(8) 0.69173(18) 0.2029(7) 0.054(2) Uani 1 1 d . . . H30E H 0.6043 0.6789 0.1826 0.065 Uiso 1 1 d R . . H30F H 0.4614 0.6936 0.1267 0.065 Uiso 1 1 d R . . C31B C 0.4446(9) 0.6747(2) 0.3096(7) 0.066(2) Uani 1 1 d . . . H31E H 0.3584 0.6865 0.3243 0.079 Uiso 1 1 d R . . H31F H 0.4221 0.6527 0.2840 0.079 Uiso 1 1 d R . . C32B C 0.5340(9) 0.6745(2) 0.4354(8) 0.070(2) Uani 1 1 d . . . H32E H 0.6215 0.6633 0.4199 0.084 Uiso 1 1 d R . . H32F H 0.4842 0.6633 0.5026 0.084 Uiso 1 1 d R . . C33B C 0.5701(8) 0.7086(2) 0.4769(6) 0.062(2) Uani 1 1 d . . . H33E H 0.4840 0.7207 0.4888 0.074 Uiso 1 1 d R . . H33F H 0.6260 0.7087 0.5569 0.074 Uiso 1 1 d R . . C34B C 0.6509(8) 0.72572(19) 0.3708(6) 0.055(2) Uani 1 1 d . . . H34E H 0.6709 0.7480 0.3938 0.066 Uiso 1 1 d R . . H34F H 0.7385 0.7141 0.3613 0.066 Uiso 1 1 d R . . O5B O 0.4177(4) 0.94539(7) 0.9432(4) 0.109(2) Uani 1 1 d G . . O6B O 0.2840(4) 0.87913(10) 1.0047(4) 0.096(2) Uani 1 1 d G . . N1B N 0.2914(4) 0.88447(9) 0.7939(4) 0.178(6) Uani 1 1 d G . . C35B C 0.5899(3) 0.90322(9) 0.9483(3) 0.079(3) Uani 1 1 d G . . C36B C 0.6869(4) 0.92540(12) 0.9990(3) 0.140(6) Uani 1 1 d G . . H36B H 0.6495 0.9456 1.0308 0.168 Uiso 1 1 d R . . C37B C 0.8136(4) 0.91915(15) 1.0204(4) 0.213(13) Uani 1 1 d G . . H37B H 0.8814 0.9357 1.0453 0.255 Uiso 1 1 d R . . C38B C 0.8654(3) 0.89418(16) 0.9929(5) 0.179(9) Uani 1 1 d G . . H38B H 0.9625 0.8888 1.0149 0.214 Uiso 1 1 d R . . C39B C 0.7926(4) 0.86540(14) 0.9395(5) 0.149(6) Uani 1 1 d G . . H39B H 0.8301 0.8443 0.9188 0.178 Uiso 1 1 d R . . C40B C 0.6372(4) 0.87317(10) 0.9117(4) 0.102(4) Uani 1 1 d G . . H40B H 0.5657 0.8600 0.8685 0.122 Uiso 1 1 d R . . C41B C 0.4483(4) 0.91683(7) 0.9305(3) 0.075(3) Uani 1 1 d G . . C42B C 0.3364(3) 0.89200(8) 0.9120(3) 0.086(3) Uani 1 1 d G . . C43B C 0.3712(4) 0.89343(12) 0.6741(3) 0.193(7) Uani 1 1 d G . . H43E H 0.4025 0.9140 0.7093 0.231 Uiso 1 1 d R . . H43F H 0.4523 0.8800 0.6577 0.231 Uiso 1 1 d R . . C44B C 0.2776(5) 0.90363(16) 0.5820(4) 0.250(12) Uani 1 1 d G . . H44E H 0.3418 0.9054 0.5114 0.301 Uiso 1 1 d R . . H44F H 0.2237 0.9234 0.5883 0.301 Uiso 1 1 d R . . C45B C 0.1731(6) 0.87217(17) 0.5629(5) 0.236(10) Uani 1 1 d G . . H45E H 0.1022 0.8803 0.5020 0.283 Uiso 1 1 d R . . H45F H 0.2242 0.8547 0.5234 0.283 Uiso 1 1 d R . . C46B C 0.0906(5) 0.86850(15) 0.6918(5) 0.234(11) Uani 1 1 d G . . H46E H 0.0345 0.8859 0.7263 0.281 Uiso 1 1 d R . . H46F H 0.0298 0.8506 0.6670 0.281 Uiso 1 1 d R . . C47B C 0.2009(5) 0.85503(12) 0.7547(5) 0.193(7) Uani 1 1 d G . . H47E H 0.2557 0.8374 0.7208 0.232 Uiso 1 1 d R . . H47F H 0.1523 0.8478 0.8304 0.232 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 O1A 0.071(4) 0.068(4) 0.059(3) -0.013(3) -0.004(3) 0.025(3) O2A 0.073(4) 0.051(3) 0.060(3) -0.019(3) -0.016(3) 0.022(3) O3A 0.038(3) 0.050(3) 0.054(3) -0.011(2) -0.003(2) 0.010(2) O4A 0.052(3) 0.049(3) 0.045(3) -0.014(2) -0.003(2) 0.013(3) C1A 0.044(5) 0.049(5) 0.051(4) -0.004(4) 0.000(4) 0.012(4) C2A 0.050(5) 0.064(5) 0.042(4) -0.009(4) -0.005(4) 0.014(5) C3A 0.033(5) 0.078(6) 0.045(4) 0.012(4) 0.002(4) -0.006(4) C4A 0.067(6) 0.056(6) 0.055(5) 0.008(4) -0.015(4) 0.006(5) C5A 0.095(8) 0.094(8) 0.070(6) 0.031(6) -0.029(6) -0.028(7) C6A 0.090(10) 0.121(10) 0.085(7) 0.063(7) -0.033(7) -0.057(8) C7A 0.073(8) 0.178(13) 0.078(7) 0.067(8) -0.005(6) -0.044(9) C8A 0.053(6) 0.114(8) 0.058(5) 0.020(5) 0.006(4) 0.006(5) C9A 0.046(5) 0.051(5) 0.046(4) -0.007(4) -0.006(4) -0.004(4) C10A 0.059(6) 0.075(6) 0.050(4) 0.003(4) -0.003(4) 0.007(5) C11A 0.035(5) 0.091(7) 0.096(7) -0.015(5) 0.000(5) -0.010(5) C12A 0.057(6) 0.066(6) 0.069(6) -0.009(4) -0.021(5) 0.002(4) C13A 0.075(7) 0.089(7) 0.047(5) -0.013(4) -0.012(5) 0.004(5) C14A 0.064(6) 0.069(5) 0.044(5) -0.005(4) -0.003(4) 0.001(5) C15A 0.035(4) 0.054(4) 0.038(4) 0.001(4) -0.004(3) 0.011(4) C16A 0.042(5) 0.064(5) 0.044(4) -0.013(4) -0.007(4) 0.011(4) C17A 0.046(5) 0.048(5) 0.073(6) 0.012(4) 0.004(4) 0.007(4) C18A 0.066(6) 0.065(6) 0.066(6) 0.018(5) 0.013(5) 0.013(5) C19A 0.076(7) 0.130(10) 0.077(6) 0.045(7) 0.030(6) 0.051(7) C20A 0.056(8) 0.126(12) 0.175(14) 0.092(11) 0.040(9) 0.024(8) C21A 0.067(8) 0.078(8) 0.159(11) 0.041(9) 0.007(9) -0.005(6) C22A 0.053(6) 0.059(6) 0.109(7) 0.023(6) -0.004(6) 0.001(5) C23A 0.038(5) 0.059(5) 0.054(5) 0.006(4) 0.005(4) -0.006(4) C24A 0.049(6) 0.058(6) 0.086(6) 0.010(4) -0.012(5) 0.013(5) C25A 0.051(6) 0.090(8) 0.090(6) -0.005(5) -0.013(5) 0.014(6) C26A 0.052(6) 0.092(8) 0.076(6) 0.015(5) -0.003(5) 0.008(6) C27A 0.050(6) 0.072(6) 0.079(6) 0.017(5) -0.014(4) -0.009(5) C28A 0.037(5) 0.065(6) 0.057(5) 0.006(4) -0.010(4) 0.006(4) C29A 0.039(5) 0.046(5) 0.054(5) -0.010(4) -0.008(4) -0.002(4) C30A 0.055(5) 0.059(5) 0.057(5) -0.013(4) 0.014(4) -0.004(4) C31A 0.071(6) 0.066(6) 0.050(5) -0.015(4) 0.008(4) 0.004(5) C32A 0.073(6) 0.064(6) 0.078(6) -0.031(5) 0.005(5) 0.000(5) C33A 0.071(6) 0.047(5) 0.073(5) -0.011(4) 0.000(5) -0.006(4) C34A 0.045(5) 0.040(4) 0.067(5) -0.003(4) -0.002(4) 0.008(4) O5A 0.140(7) 0.069(5) 0.111(5) 0.006(4) -0.008(4) -0.023(5) O6A 0.110(5) 0.068(4) 0.089(4) 0.033(3) -0.034(4) -0.025(4) N1A 0.126(8) 0.109(7) 0.089(6) 0.009(5) -0.012(6) 0.033(6) C35A 0.086(7) 0.056(6) 0.067(6) 0.010(5) -0.015(5) -0.002(6) C36A 0.098(10) 0.114(9) 0.086(7) -0.021(6) 0.016(7) -0.011(8) C37A 0.147(15) 0.112(11) 0.099(8) 0.002(8) 0.007(9) 0.036(10) C38A 0.120(12) 0.152(15) 0.136(11) 0.049(11) 0.009(9) 0.018(12) C39A 0.108(10) 0.086(9) 0.167(11) 0.060(9) -0.055(9) -0.050(8) C40A 0.117(10) 0.061(7) 0.111(8) 0.005(5) -0.022(7) -0.011(7) C41A 0.116(10) 0.061(7) 0.087(7) 0.010(5) -0.011(6) -0.018(7) C42A 0.091(8) 0.069(7) 0.076(7) 0.007(6) -0.014(6) -0.022(6) C43A 0.130(11) 0.141(11) 0.113(9) -0.003(8) -0.025(9) 0.034(9) C44A 0.187(14) 0.132(11) 0.130(10) 0.053(9) 0.054(10) 0.046(11) C45A 0.27(2) 0.126(11) 0.142(11) 0.055(9) 0.080(12) 0.082(12) C46A 0.138(12) 0.119(10) 0.241(16) 0.054(11) 0.101(13) 0.017(9) C47A 0.131(12) 0.149(12) 0.162(12) 0.001(10) 0.001(10) 0.042(11) O1B 0.075(4) 0.049(3) 0.059(3) 0.009(3) 0.014(3) 0.016(3) O2B 0.070(4) 0.058(4) 0.053(3) 0.015(3) 0.007(3) 0.019(3) O3B 0.047(3) 0.052(3) 0.053(3) 0.010(3) 0.014(2) 0.017(3) O4B 0.039(3) 0.055(3) 0.051(3) 0.019(2) 0.005(2) 0.010(3) C1B 0.042(4) 0.039(4) 0.053(4) -0.002(4) 0.001(4) 0.002(4) C2B 0.049(5) 0.036(4) 0.056(4) 0.004(4) 0.012(4) 0.006(4) C3B 0.045(5) 0.053(5) 0.048(4) -0.004(4) -0.001(4) 0.005(4) C4B 0.050(5) 0.051(5) 0.086(6) 0.007(5) 0.015(4) 0.006(4) C5B 0.051(5) 0.054(6) 0.087(6) -0.004(5) 0.017(5) 0.000(5) C6B 0.040(5) 0.086(7) 0.078(6) 0.002(5) 0.011(4) -0.004(5) C7B 0.050(6) 0.079(7) 0.083(6) -0.007(5) 0.017(5) 0.028(5) C8B 0.050(6) 0.061(6) 0.078(5) -0.001(4) 0.008(4) 0.009(5) C9B 0.044(5) 0.047(5) 0.064(5) -0.014(4) 0.001(4) 0.012(4) C10B 0.069(6) 0.056(6) 0.073(6) -0.021(5) -0.004(5) 0.019(5) C11B 0.103(10) 0.114(10) 0.096(8) -0.038(8) -0.035(8) 0.033(8) C12B 0.075(9) 0.153(15) 0.149(12) -0.076(12) -0.045(10) 0.047(9) C13B 0.053(7) 0.088(9) 0.226(14) -0.095(11) 0.002(10) -0.017(6) C14B 0.066(6) 0.067(7) 0.110(7) -0.015(6) 0.033(6) -0.004(6) C15B 0.042(4) 0.044(4) 0.039(4) 0.008(3) 0.007(3) 0.006(4) C16B 0.039(4) 0.052(5) 0.043(4) 0.002(4) 0.008(3) 0.009(4) C17B 0.043(5) 0.057(5) 0.043(4) -0.002(4) 0.004(4) 0.001(4) C18B 0.055(5) 0.058(6) 0.049(4) 0.006(4) 0.006(4) -0.003(5) C19B 0.086(8) 0.057(6) 0.065(5) -0.008(5) 0.011(5) 0.002(6) C20B 0.113(10) 0.096(9) 0.057(5) -0.017(6) 0.008(6) -0.046(8) C21B 0.066(7) 0.111(9) 0.081(7) -0.022(6) 0.001(5) -0.012(7) C22B 0.048(6) 0.088(7) 0.054(5) -0.009(4) 0.000(4) -0.008(5) C23B 0.043(5) 0.044(4) 0.053(5) 0.009(4) 0.005(4) 0.006(4) C24B 0.060(6) 0.075(6) 0.049(5) 0.002(4) 0.008(4) -0.003(5) C25B 0.066(7) 0.103(7) 0.057(5) 0.014(5) 0.016(5) -0.003(6) C26B 0.081(8) 0.099(7) 0.070(6) 0.004(5) 0.041(6) -0.004(6) C27B 0.050(6) 0.084(7) 0.091(7) 0.015(5) -0.002(5) -0.016(5) C28B 0.054(6) 0.084(6) 0.061(5) 0.009(5) 0.013(5) 0.000(5) C29B 0.036(4) 0.042(5) 0.052(4) 0.008(4) 0.017(4) 0.005(4) C30B 0.051(5) 0.056(5) 0.055(5) 0.001(4) 0.002(4) 0.000(4) C31B 0.068(6) 0.062(6) 0.068(5) 0.005(4) 0.014(5) -0.009(4) C32B 0.061(6) 0.079(7) 0.071(5) 0.027(5) 0.011(5) 0.000(5) C33B 0.066(6) 0.079(7) 0.040(4) 0.013(4) 0.001(4) -0.006(5) C34B 0.056(5) 0.060(5) 0.049(4) 0.010(4) 0.008(4) 0.005(4) O5B 0.118(6) 0.066(4) 0.144(6) 0.016(4) 0.029(5) 0.026(4) O6B 0.103(5) 0.084(5) 0.101(4) 0.026(4) 0.027(4) 0.022(4) N1B 0.209(12) 0.248(13) 0.079(6) 0.004(7) 0.044(7) -0.137(11) C35B 0.102(9) 0.072(7) 0.062(5) 0.010(5) 0.008(6) -0.012(6) C36B 0.127(13) 0.199(16) 0.094(9) 0.025(9) 0.024(9) 0.063(11) C37B 0.44(4) 0.132(13) 0.071(8) -0.025(8) 0.017(14) -0.004(17) C38B 0.099(10) 0.33(3) 0.105(10) 0.065(14) -0.026(8) -0.069(15) C39B 0.181(14) 0.121(10) 0.149(10) 0.078(9) 0.100(11) 0.110(10) C40B 0.135(10) 0.071(7) 0.102(7) 0.007(6) 0.052(7) 0.008(7) C41B 0.089(8) 0.069(7) 0.066(5) 0.009(5) 0.012(5) 0.002(6) C42B 0.104(8) 0.088(8) 0.068(6) 0.021(6) 0.023(6) 0.000(6) C43B 0.201(17) 0.229(18) 0.147(12) 0.013(11) -0.007(11) -0.077(14) C44B 0.195(17) 0.33(3) 0.223(18) 0.224(19) -0.086(14) -0.045(17) C45B 0.199(18) 0.26(2) 0.240(18) -0.149(17) -0.080(15) -0.041(16) C46B 0.148(15) 0.26(2) 0.30(2) 0.189(18) 0.061(14) 0.082(13) C47B 0.138(13) 0.097(10) 0.34(2) 0.035(13) -0.026(14) -0.021(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 C2A 1.458(8) . ? O1A H1OA 0.8200 . ? O2A C16A 1.432(7) . ? O2A H2OA 0.8200 . ? O3A C29A 1.435(7) . ? O3A C1A 1.445(7) . ? O4A C15A 1.403(7) . ? O4A C29A 1.441(8) . ? C1A C15A 1.532(9) . ? C1A C2A 1.570(9) . ? C1A H1A 0.9598 . ? C2A C3A 1.505(10) . ? C2A C9A 1.536(9) . ? C3A C4A 1.370(10) . ? C3A C8A 1.410(10) . ? C4A C5A 1.381(11) . ? C4A H4A 0.9600 . ? C5A C6A 1.391(14) . ? C5A H5A 0.9599 . ? C6A C7A 1.314(15) . ? C6A H6A 0.9600 . ? C7A C8A 1.361(14) . ? C7A H7A 0.9600 . ? C8A H8A 0.9600 . ? C9A C10A 1.379(9) . ? C9A C14A 1.392(9) . ? C10A C11A 1.408(10) . ? C10A H10A 0.9600 . ? C11A C12A 1.357(10) . ? C11A H11A 0.9601 . ? C12A C13A 1.384(11) . ? C12A H12A 0.9599 . ? C13A C14A 1.408(10) . ? C13A H13A 0.9599 . ? C14A H14A 0.9601 . ? C15A C16A 1.556(9) . ? C15A H15A 0.9602 . ? C16A C23A 1.515(9) . ? C16A C17A 1.561(10) . ? C17A C22A 1.360(11) . ? C17A C18A 1.370(10) . ? C18A C19A 1.404(12) . ? C18A H18A 0.9599 . ? C19A C20A 1.443(16) . ? C19A H19A 0.9601 . ? C20A C21A 1.272(15) . ? C20A H20A 0.9599 . ? C21A C22A 1.346(13) . ? C21A H21A 0.9601 . ? C22A H22A 0.9600 . ? C23A C28A 1.375(10) . ? C23A C24A 1.412(10) . ? C24A C25A 1.373(10) . ? C24A H24A 0.9601 . ? C25A C26A 1.381(12) . ? C25A H25A 0.9599 . ? C26A C27A 1.369(11) . ? C26A H26A 0.9599 . ? C27A C28A 1.408(10) . ? C27A H27A 0.9597 . ? C28A H28A 0.9603 . ? C29A C30A 1.497(9) . ? C29A C34A 1.507(9) . ? C30A C31A 1.548(10) . ? C30A H30C 0.9600 . ? C30A H30D 0.9603 . ? C31A C32A 1.500(10) . ? C31A H31C 0.9601 . ? C31A H31D 0.9600 . ? C32A C33A 1.525(9) . ? C32A H32C 0.9600 . ? C32A H32D 0.9599 . ? C33A C34A 1.528(9) . ? C33A H33C 0.9603 . ? C33A H33D 0.9599 . ? C34A H34C 0.9600 . ? C34A H34D 0.9601 . ? O5A C41A 1.219(10) . ? O6A C42A 1.209(10) . ? N1A C42A 1.324(11) . ? N1A C47A 1.445(13) . ? N1A C43A 1.525(13) . ? C35A C36A 1.381(12) . ? C35A C40A 1.417(12) . ? C35A C41A 1.439(13) . ? C36A C37A 1.350(15) . ? C36A H36A 0.9597 . ? C37A C38A 1.385(17) . ? C37A H37A 0.9600 . ? C38A C39A 1.368(16) . ? C38A H38A 0.9600 . ? C39A C40A 1.411(14) . ? C39A H39A 0.9603 . ? C40A H40A 0.9598 . ? C41A C42A 1.543(13) . ? C43A C44A 1.388(14) . ? C43A H43C 0.9601 . ? C43A H43D 0.9599 . ? C44A C45A 1.505(15) . ? C44A H44C 0.9599 . ? C44A H44D 0.9600 . ? C45A C46A 1.547(18) . ? C45A H45C 0.9601 . ? C45A H45D 0.9600 . ? C46A C47A 1.398(15) . ? C46A H46C 0.9601 . ? C46A H46D 0.9599 . ? C47A H47C 0.9597 . ? C47A H47D 0.9595 . ? O1B C2B 1.449(7) . ? O1B H1OB 0.8200 . ? O2B C16B 1.433(8) . ? O2B H2OB 0.8200 . ? O3B C1B 1.418(7) . ? O3B C29B 1.417(7) . ? O4B C15B 1.426(7) . ? O4B C29B 1.429(7) . ? C1B C2B 1.557(9) . ? C1B C15B 1.575(9) . ? C1B H1B 0.9599 . ? C2B C3B 1.521(10) . ? C2B C9B 1.535(10) . ? C3B C8B 1.371(10) . ? C3B C4B 1.403(10) . ? C4B C5B 1.394(10) . ? C4B H4B 0.9599 . ? C5B C6B 1.350(10) . ? C5B H5B 0.9597 . ? C6B C7B 1.377(11) . ? C6B H6B 0.9600 . ? C7B C8B 1.387(10) . ? C7B H7B 0.9600 . ? C8B H8B 0.9600 . ? C9B C14B 1.378(10) . ? C9B C10B 1.400(10) . ? C10B C11B 1.371(13) . ? C10B H10B 0.9601 . ? C11B C12B 1.348(16) . ? C11B H11B 0.9601 . ? C12B C13B 1.366(16) . ? C12B H12B 0.9599 . ? C13B C14B 1.406(14) . ? C13B H13B 0.9598 . ? C14B H14B 0.9601 . ? C15B C16B 1.557(8) . ? C15B H15B 0.9599 . ? C16B C23B 1.537(9) . ? C16B C17B 1.525(9) . ? C17B C22B 1.385(10) . ? C17B C18B 1.398(9) . ? C18B C19B 1.378(11) . ? C18B H18B 0.9600 . ? C19B C20B 1.370(12) . ? C19B H19B 0.9597 . ? C20B C21B 1.379(13) . ? C20B H20B 0.9601 . ? C21B C22B 1.374(12) . ? C21B H21B 0.9600 . ? C22B H22B 0.9597 . ? C23B C28B 1.364(10) . ? C23B C24B 1.404(9) . ? C24B C25B 1.383(10) . ? C24B H24B 0.9600 . ? C25B C26B 1.366(11) . ? C25B H25B 0.9599 . ? C26B C27B 1.390(11) . ? C26B H26B 0.9599 . ? C27B C28B 1.402(10) . ? C27B H27B 0.9600 . ? C28B H28B 0.9600 . ? C29B C34B 1.511(9) . ? C29B C30B 1.517(9) . ? C30B C31B 1.507(9) . ? C30B H30E 0.9601 . ? C30B H30F 0.9599 . ? C31B C32B 1.518(10) . ? C31B H31E 0.9602 . ? C31B H31F 0.9597 . ? C32B C33B 1.498(10) . ? C32B H32E 0.9599 . ? C32B H32F 0.9601 . ? C33B C34B 1.517(9) . ? C33B H33E 0.9602 . ? C33B H33F 0.9599 . ? C34B H34E 0.9598 . ? C34B H34F 0.9600 . ? O5B C41B 1.2129 . ? O6B C42B 1.2058 . ? N1B C42B 1.3065 . ? N1B C43B 1.5045 . ? N1B C47B 1.5238 . ? C35B C40B 1.3659 . ? C35B C36B 1.3785 . ? C35B C41B 1.4510 . ? C36B C37B 1.2338 . ? C36B H36B 0.9601 . ? C37B C38B 1.1713 . ? C37B H37B 0.9600 . ? C38B C39B 1.4615 . ? C38B H38B 0.9601 . ? C39B C40B 1.5167 . ? C39B H39B 0.9601 . ? C40B H40B 0.9601 . ? C41B C42B 1.4731 . ? C43B C44B 1.3388 . ? C43B H43E 0.9598 . ? C43B H43F 0.9601 . ? C44B C45B 1.6295 . ? C44B H44E 0.9599 . ? C44B H44F 0.9602 . ? C45B C46B 1.5606 . ? C45B H45E 0.9599 . ? C45B H45F 0.9601 . ? C46B C47B 1.3255 . ? C46B H46E 0.9600 . ? C46B H46F 0.9602 . ? C47B H47E 0.9598 . ? C47B H47F 0.9599 . ? 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 C2A O1A H1OA 109.5 . . ? C16A O2A H2OA 109.5 . . ? C29A O3A C1A 110.2(5) . . ? C15A O4A C29A 109.5(5) . . ? O3A C1A C15A 103.9(5) . . ? O3A C1A C2A 107.4(5) . . ? C15A C1A C2A 118.6(5) . . ? O3A C1A H1A 112.1 . . ? C15A C1A H1A 105.9 . . ? C2A C1A H1A 109.0 . . ? O1A C2A C3A 110.2(6) . . ? O1A C2A C9A 103.4(6) . . ? C3A C2A C9A 110.5(6) . . ? O1A C2A C1A 107.4(5) . . ? C3A C2A C1A 112.2(6) . . ? C9A C2A C1A 112.9(5) . . ? C4A C3A C8A 117.0(8) . . ? C4A C3A C2A 121.9(7) . . ? C8A C3A C2A 121.1(8) . . ? C3A C4A C5A 121.7(9) . . ? C3A C4A H4A 117.8 . . ? C5A C4A H4A 120.5 . . ? C6A C5A C4A 118.7(10) . . ? C6A C5A H5A 121.3 . . ? C4A C5A H5A 119.9 . . ? C7A C6A C5A 120.4(10) . . ? C7A C6A H6A 118.9 . . ? C5A C6A H6A 120.6 . . ? C6A C7A C8A 121.9(11) . . ? C6A C7A H7A 117.5 . . ? C8A C7A H7A 120.5 . . ? C7A C8A C3A 120.3(10) . . ? C7A C8A H8A 122.4 . . ? C3A C8A H8A 117.2 . . ? C10A C9A C14A 118.5(7) . . ? C10A C9A C2A 125.4(6) . . ? C14A C9A C2A 116.1(6) . . ? C9A C10A C11A 120.7(7) . . ? C9A C10A H10A 119.1 . . ? C11A C10A H10A 120.1 . . ? C12A C11A C10A 120.8(8) . . ? C12A C11A H11A 120.6 . . ? C10A C11A H11A 118.6 . . ? C11A C12A C13A 119.2(8) . . ? C11A C12A H12A 122.1 . . ? C13A C12A H12A 118.7 . . ? C12A C13A C14A 120.6(7) . . ? C12A C13A H13A 121.3 . . ? C14A C13A H13A 118.1 . . ? C13A C14A C9A 120.0(7) . . ? C13A C14A H14A 122.1 . . ? C9A C14A H14A 117.8 . . ? O4A C15A C1A 103.9(5) . . ? O4A C15A C16A 107.3(5) . . ? C1A C15A C16A 117.3(6) . . ? O4A C15A H15A 114.5 . . ? C1A C15A H15A 107.2 . . ? C16A C15A H15A 107.0 . . ? O2A C16A C23A 109.7(5) . . ? O2A C16A C15A 101.8(5) . . ? C23A C16A C15A 113.2(6) . . ? O2A C16A C17A 111.3(6) . . ? C23A C16A C17A 110.0(6) . . ? C15A C16A C17A 110.6(5) . . ? C22A C17A C18A 119.0(8) . . ? C22A C17A C16A 121.3(8) . . ? C18A C17A C16A 119.6(7) . . ? C17A C18A C19A 118.4(9) . . ? C17A C18A H18A 118.3 . . ? C19A C18A H18A 123.2 . . ? C18A C19A C20A 118.3(10) . . ? C18A C19A H19A 120.8 . . ? C20A C19A H19A 120.9 . . ? C21A C20A C19A 120.3(12) . . ? C21A C20A H20A 121.5 . . ? C19A C20A H20A 118.2 . . ? C20A C21A C22A 121.3(13) . . ? C20A C21A H21A 120.8 . . ? C22A C21A H21A 117.9 . . ? C21A C22A C17A 122.6(10) . . ? C21A C22A H22A 119.9 . . ? C17A C22A H22A 117.4 . . ? C28A C23A C24A 117.8(7) . . ? C28A C23A C16A 124.4(7) . . ? C24A C23A C16A 117.7(7) . . ? C25A C24A C23A 120.4(8) . . ? C25A C24A H24A 121.0 . . ? C23A C24A H24A 118.6 . . ? C24A C25A C26A 120.6(9) . . ? C24A C25A H25A 120.1 . . ? C26A C25A H25A 119.3 . . ? C27A C26A C25A 120.6(8) . . ? C27A C26A H26A 119.4 . . ? C25A C26A H26A 119.9 . . ? C26A C27A C28A 118.7(8) . . ? C26A C27A H27A 120.5 . . ? C28A C27A H27A 120.7 . . ? C23A C28A C27A 121.8(7) . . ? C23A C28A H28A 119.4 . . ? C27A C28A H28A 118.8 . . ? O3A C29A O4A 104.9(5) . . ? O3A C29A C30A 109.1(6) . . ? O4A C29A C30A 107.4(5) . . ? O3A C29A C34A 111.3(5) . . ? O4A C29A C34A 110.4(5) . . ? C30A C29A C34A 113.3(6) . . ? C29A C30A C31A 111.5(6) . . ? C29A C30A H30C 108.8 . . ? C31A C30A H30C 110.9 . . ? C29A C30A H30D 108.4 . . ? C31A C30A H30D 107.8 . . ? H30C C30A H30D 109.5 . . ? C32A C31A C30A 111.6(6) . . ? C32A C31A H31C 106.2 . . ? C30A C31A H31C 106.9 . . ? C32A C31A H31D 110.8 . . ? C30A C31A H31D 111.6 . . ? H31C C31A H31D 109.5 . . ? C31A C32A C33A 111.5(6) . . ? C31A C32A H32C 110.7 . . ? C33A C32A H32C 110.6 . . ? C31A C32A H32D 106.4 . . ? C33A C32A H32D 107.9 . . ? H32C C32A H32D 109.5 . . ? C34A C33A C32A 111.4(6) . . ? C34A C33A H33C 109.3 . . ? C32A C33A H33C 110.4 . . ? C34A C33A H33D 108.3 . . ? C32A C33A H33D 107.9 . . ? H33C C33A H33D 109.5 . . ? C29A C34A C33A 112.0(6) . . ? C29A C34A H34C 109.0 . . ? C33A C34A H34C 107.8 . . ? C29A C34A H34D 108.3 . . ? C33A C34A H34D 110.2 . . ? H34C C34A H34D 109.5 . . ? C42A N1A C47A 123.0(10) . . ? C42A N1A C43A 124.0(10) . . ? C47A N1A C43A 113.0(9) . . ? C36A C35A C40A 118.0(10) . . ? C36A C35A C41A 119.3(9) . . ? C40A C35A C41A 122.8(10) . . ? C37A C36A C35A 123.5(12) . . ? C37A C36A H36A 119.5 . . ? C35A C36A H36A 116.9 . . ? C38A C37A C36A 118.2(13) . . ? C38A C37A H37A 122.3 . . ? C36A C37A H37A 119.5 . . ? C37A C38A C39A 121.8(15) . . ? C37A C38A H38A 118.2 . . ? C39A C38A H38A 120.0 . . ? C38A C39A C40A 119.6(12) . . ? C38A C39A H39A 120.2 . . ? C40A C39A H39A 120.2 . . ? C39A C40A C35A 118.8(11) . . ? C39A C40A H40A 121.8 . . ? C35A C40A H40A 119.4 . . ? O5A C41A C35A 124.2(11) . . ? O5A C41A C42A 117.6(10) . . ? C35A C41A C42A 117.8(9) . . ? O6A C42A N1A 124.8(10) . . ? O6A C42A C41A 118.0(9) . . ? N1A C42A C41A 117.1(9) . . ? C44A C43A N1A 113.9(10) . . ? C44A C43A H43C 106.6 . . ? N1A C43A H43C 109.0 . . ? C44A C43A H43D 109.7 . . ? N1A C43A H43D 108.1 . . ? H43C C43A H43D 109.5 . . ? C43A C44A C45A 109.7(11) . . ? C43A C44A H44C 112.2 . . ? C45A C44A H44C 113.0 . . ? C43A C44A H44D 106.5 . . ? C45A C44A H44D 105.5 . . ? H44C C44A H44D 109.5 . . ? C44A C45A C46A 109.3(11) . . ? C44A C45A H45C 113.7 . . ? C46A C45A H45C 113.1 . . ? C44A C45A H45D 105.1 . . ? C46A C45A H45D 105.6 . . ? H45C C45A H45D 109.5 . . ? C47A C46A C45A 112.0(13) . . ? C47A C46A H46C 111.9 . . ? C45A C46A H46C 109.1 . . ? C47A C46A H46D 108.2 . . ? C45A C46A H46D 105.9 . . ? H46C C46A H46D 109.5 . . ? C46A C47A N1A 111.9(12) . . ? C46A C47A H47C 112.6 . . ? N1A C47A H47C 108.3 . . ? C46A C47A H47D 106.8 . . ? N1A C47A H47D 107.7 . . ? H47C C47A H47D 109.5 . . ? C2B O1B H1OB 109.5 . . ? C16B O2B H2OB 109.5 . . ? C1B O3B C29B 110.5(4) . . ? C15B O4B C29B 111.6(5) . . ? O3B C1B C2B 108.6(5) . . ? O3B C1B C15B 103.3(5) . . ? C2B C1B C15B 114.8(5) . . ? O3B C1B H1B 113.5 . . ? C2B C1B H1B 106.6 . . ? C15B C1B H1B 110.1 . . ? O1B C2B C3B 107.6(6) . . ? O1B C2B C9B 111.4(6) . . ? C3B C2B C9B 111.0(6) . . ? O1B C2B C1B 100.7(5) . . ? C3B C2B C1B 112.6(6) . . ? C9B C2B C1B 113.1(6) . . ? C8B C3B C4B 116.9(7) . . ? C8B C3B C2B 119.0(7) . . ? C4B C3B C2B 124.0(7) . . ? C5B C4B C3B 119.9(7) . . ? C5B C4B H4B 121.2 . . ? C3B C4B H4B 118.9 . . ? C6B C5B C4B 121.5(8) . . ? C6B C5B H5B 119.8 . . ? C4B C5B H5B 118.7 . . ? C5B C6B C7B 119.7(7) . . ? C5B C6B H6B 121.0 . . ? C7B C6B H6B 119.2 . . ? C6B C7B C8B 119.0(8) . . ? C6B C7B H7B 120.1 . . ? C8B C7B H7B 120.9 . . ? C3B C8B C7B 122.9(8) . . ? C3B C8B H8B 118.2 . . ? C7B C8B H8B 118.9 . . ? C14B C9B C10B 119.1(8) . . ? C14B C9B C2B 122.5(7) . . ? C10B C9B C2B 118.4(7) . . ? C11B C10B C9B 119.7(9) . . ? C11B C10B H10B 120.0 . . ? C9B C10B H10B 120.3 . . ? C12B C11B C10B 122.6(13) . . ? C12B C11B H11B 118.6 . . ? C10B C11B H11B 118.8 . . ? C11B C12B C13B 117.8(14) . . ? C11B C12B H12B 118.3 . . ? C13B C12B H12B 123.9 . . ? C12B C13B C14B 122.4(13) . . ? C12B C13B H13B 119.1 . . ? C14B C13B H13B 118.6 . . ? C9B C14B C13B 118.3(10) . . ? C9B C14B H14B 116.9 . . ? C13B C14B H14B 124.8 . . ? O4B C15B C16B 109.9(5) . . ? O4B C15B C1B 103.3(5) . . ? C16B C15B C1B 116.7(6) . . ? O4B C15B H15B 112.3 . . ? C16B C15B H15B 107.3 . . ? C1B C15B H15B 107.3 . . ? O2B C16B C23B 104.2(5) . . ? O2B C16B C17B 108.6(6) . . ? C23B C16B C17B 109.8(5) . . ? O2B C16B C15B 109.1(5) . . ? C23B C16B C15B 111.8(6) . . ? C17B C16B C15B 112.9(5) . . ? C22B C17B C18B 117.7(7) . . ? C22B C17B C16B 121.8(7) . . ? C18B C17B C16B 120.5(7) . . ? C19B C18B C17B 119.9(8) . . ? C19B C18B H18B 121.7 . . ? C17B C18B H18B 118.4 . . ? C20B C19B C18B 121.1(9) . . ? C20B C19B H19B 119.5 . . ? C18B C19B H19B 119.4 . . ? C19B C20B C21B 119.9(9) . . ? C19B C20B H20B 118.9 . . ? C21B C20B H20B 121.1 . . ? C22B C21B C20B 119.0(10) . . ? C22B C21B H21B 120.3 . . ? C20B C21B H21B 120.7 . . ? C21B C22B C17B 122.3(9) . . ? C21B C22B H22B 119.9 . . ? C17B C22B H22B 117.8 . . ? C28B C23B C24B 118.2(6) . . ? C28B C23B C16B 125.3(6) . . ? C24B C23B C16B 116.4(7) . . ? C25B C24B C23B 121.1(8) . . ? C25B C24B H24B 120.5 . . ? C23B C24B H24B 118.3 . . ? C24B C25B C26B 120.6(8) . . ? C24B C25B H25B 121.8 . . ? C26B C25B H25B 117.6 . . ? C25B C26B C27B 118.8(8) . . ? C25B C26B H26B 120.2 . . ? C27B C26B H26B 120.9 . . ? C26B C27B C28B 120.6(8) . . ? C26B C27B H27B 119.0 . . ? C28B C27B H27B 120.2 . . ? C23B C28B C27B 120.6(7) . . ? C23B C28B H28B 118.1 . . ? C27B C28B H28B 121.1 . . ? O3B C29B O4B 105.9(5) . . ? O3B C29B C34B 107.8(5) . . ? O4B C29B C34B 109.6(5) . . ? O3B C29B C30B 110.9(6) . . ? O4B C29B C30B 111.5(5) . . ? C34B C29B C30B 111.0(6) . . ? C31B C30B C29B 112.2(6) . . ? C31B C30B H30E 108.4 . . ? C29B C30B H30E 109.9 . . ? C31B C30B H30F 109.5 . . ? C29B C30B H30F 107.3 . . ? H30E C30B H30F 109.5 . . ? C30B C31B C32B 110.4(7) . . ? C30B C31B H31E 108.4 . . ? C32B C31B H31E 108.6 . . ? C30B C31B H31F 110.1 . . ? C32B C31B H31F 109.7 . . ? H31E C31B H31F 109.5 . . ? C33B C32B C31B 110.5(7) . . ? C33B C32B H32E 107.6 . . ? C31B C32B H32E 108.6 . . ? C33B C32B H32F 110.6 . . ? C31B C32B H32F 110.0 . . ? H32E C32B H32F 109.5 . . ? C32B C33B C34B 110.0(6) . . ? C32B C33B H33E 109.3 . . ? C34B C33B H33E 107.3 . . ? C32B C33B H33F 111.0 . . ? C34B C33B H33F 109.7 . . ? H33E C33B H33F 109.4 . . ? C29B C34B C33B 112.0(6) . . ? C29B C34B H34E 107.5 . . ? C33B C34B H34E 111.3 . . ? C29B C34B H34F 109.5 . . ? C33B C34B H34F 107.2 . . ? H34E C34B H34F 109.5 . . ? C42B N1B C43B 122.8 . . ? C42B N1B C47B 126.4 . . ? C43B N1B C47B 105.5 . . ? C40B C35B C36B 118.7 . . ? C40B C35B C41B 128.1 . . ? C36B C35B C41B 112.9 . . ? C37B C36B C35B 123.8 . . ? C37B C36B H36B 118.8 . . ? C35B C36B H36B 116.8 . . ? C38B C37B C36B 123.1 . . ? C38B C37B H37B 113.7 . . ? C36B C37B H37B 122.1 . . ? C37B C38B C39B 126.9 . . ? C37B C38B H38B 122.9 . . ? C39B C38B H38B 109.6 . . ? C38B C39B C40B 109.9 . . ? C38B C39B H39B 129.6 . . ? C40B C39B H39B 120.4 . . ? C35B C40B C39B 117.3 . . ? C35B C40B H40B 113.9 . . ? C39B C40B H40B 128.9 . . ? O5B C41B C35B 125.3 . . ? O5B C41B C42B 120.5 . . ? C35B C41B C42B 113.7 . . ? O6B C42B N1B 119.9 . . ? O6B C42B C41B 120.6 . . ? N1B C42B C41B 119.5 . . ? C44B C43B N1B 108.5 . . ? C44B C43B H43E 100.3 . . ? N1B C43B H43E 93.6 . . ? C44B C43B H43F 124.4 . . ? N1B C43B H43F 115.0 . . ? H43E C43B H43F 109.5 . . ? C43B C44B C45B 102.7 . . ? C43B C44B H44E 98.0 . . ? C45B C44B H44E 111.2 . . ? C43B C44B H44F 123.7 . . ? C45B C44B H44F 111.0 . . ? H44E C44B H44F 109.5 . . ? C46B C45B C44B 106.8 . . ? C46B C45B H45E 103.3 . . ? C44B C45B H45E 102.0 . . ? C46B C45B H45F 123.6 . . ? C44B C45B H45F 109.5 . . ? H45E C45B H45F 109.5 . . ? C47B C46B C45B 92.8 . . ? C47B C46B H46E 124.1 . . ? C45B C46B H46E 122.3 . . ? C47B C46B H46F 105.2 . . ? C45B C46B H46F 99.0 . . ? H46E C46B H46F 109.5 . . ? C46B C47B N1B 102.8 . . ? C46B C47B H47E 124.0 . . ? N1B C47B H47E 112.9 . . ? C46B C47B H47F 97.9 . . ? N1B C47B H47F 108.0 . . ? H47E C47B H47F 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 C29A O3A C1A C15A -8.7(6) . . . . ? C29A O3A C1A C2A -135.1(5) . . . . ? O3A C1A C2A O1A 179.4(5) . . . . ? C15A C1A C2A O1A 62.2(8) . . . . ? O3A C1A C2A C3A 58.2(7) . . . . ? C15A C1A C2A C3A -58.9(8) . . . . ? O3A C1A C2A C9A -67.3(7) . . . . ? C15A C1A C2A C9A 175.5(6) . . . . ? O1A C2A C3A C4A 159.1(6) . . . . ? C9A C2A C3A C4A 45.6(9) . . . . ? C1A C2A C3A C4A -81.3(8) . . . . ? O1A C2A C3A C8A -22.0(9) . . . . ? C9A C2A C3A C8A -135.6(7) . . . . ? C1A C2A C3A C8A 97.6(7) . . . . ? C8A C3A C4A C5A -2.0(11) . . . . ? C2A C3A C4A C5A 177.0(7) . . . . ? C3A C4A C5A C6A 0.7(12) . . . . ? C4A C5A C6A C7A 0.7(15) . . . . ? C5A C6A C7A C8A -0.8(17) . . . . ? C6A C7A C8A C3A -0.5(15) . . . . ? C4A C3A C8A C7A 1.9(11) . . . . ? C2A C3A C8A C7A -177.1(8) . . . . ? O1A C2A C9A C10A 120.9(8) . . . . ? C3A C2A C9A C10A -121.2(8) . . . . ? C1A C2A C9A C10A 5.3(10) . . . . ? O1A C2A C9A C14A -58.9(8) . . . . ? C3A C2A C9A C14A 58.9(8) . . . . ? C1A C2A C9A C14A -174.6(6) . . . . ? C14A C9A C10A C11A 1.6(12) . . . . ? C2A C9A C10A C11A -178.2(7) . . . . ? C9A C10A C11A C12A 0.5(13) . . . . ? C10A C11A C12A C13A -1.3(12) . . . . ? C11A C12A C13A C14A 0.1(12) . . . . ? C12A C13A C14A C9A 2.1(12) . . . . ? C10A C9A C14A C13A -2.9(11) . . . . ? C2A C9A C14A C13A 177.0(7) . . . . ? C29A O4A C15A C1A -28.6(6) . . . . ? C29A O4A C15A C16A -153.4(5) . . . . ? O3A C1A C15A O4A 22.3(6) . . . . ? C2A C1A C15A O4A 141.3(6) . . . . ? O3A C1A C15A C16A 140.5(5) . . . . ? C2A C1A C15A C16A -100.5(7) . . . . ? O4A C15A C16A O2A 174.5(5) . . . . ? C1A C15A C16A O2A 58.2(7) . . . . ? O4A C15A C16A C23A -67.8(7) . . . . ? C1A C15A C16A C23A 175.9(5) . . . . ? O4A C15A C16A C17A 56.1(7) . . . . ? C1A C15A C16A C17A -60.2(7) . . . . ? O2A C16A C17A C22A -7.6(9) . . . . ? C23A C16A C17A C22A -129.4(8) . . . . ? C15A C16A C17A C22A 104.8(8) . . . . ? O2A C16A C17A C18A 171.1(6) . . . . ? C23A C16A C17A C18A 49.3(9) . . . . ? C15A C16A C17A C18A -76.5(8) . . . . ? C22A C17A C18A C19A -3.6(11) . . . . ? C16A C17A C18A C19A 177.6(7) . . . . ? C17A C18A C19A C20A 2.5(12) . . . . ? C18A C19A C20A C21A -0.4(16) . . . . ? C19A C20A C21A C22A -0.6(18) . . . . ? C20A C21A C22A C17A -0.6(16) . . . . ? C18A C17A C22A C21A 2.8(12) . . . . ? C16A C17A C22A C21A -178.5(8) . . . . ? O2A C16A C23A C28A 122.2(7) . . . . ? C15A C16A C23A C28A 9.2(9) . . . . ? C17A C16A C23A C28A -115.0(7) . . . . ? O2A C16A C23A C24A -55.0(8) . . . . ? C15A C16A C23A C24A -168.0(6) . . . . ? C17A C16A C23A C24A 67.8(8) . . . . ? C28A C23A C24A C25A 0.5(10) . . . . ? C16A C23A C24A C25A 177.8(7) . . . . ? C23A C24A C25A C26A -0.3(12) . . . . ? C24A C25A C26A C27A 0.0(12) . . . . ? C25A C26A C27A C28A 0.2(11) . . . . ? C24A C23A C28A C27A -0.3(10) . . . . ? C16A C23A C28A C27A -177.4(6) . . . . ? C26A C27A C28A C23A -0.1(11) . . . . ? C1A O3A C29A O4A -7.9(6) . . . . ? C1A O3A C29A C30A -122.8(6) . . . . ? C1A O3A C29A C34A 111.5(6) . . . . ? C15A O4A C29A O3A 23.5(6) . . . . ? C15A O4A C29A C30A 139.5(6) . . . . ? C15A O4A C29A C34A -96.5(6) . . . . ? O3A C29A C30A C31A -176.7(6) . . . . ? O4A C29A C30A C31A 70.1(7) . . . . ? C34A C29A C30A C31A -52.2(8) . . . . ? C29A C30A C31A C32A 53.6(9) . . . . ? C30A C31A C32A C33A -55.1(9) . . . . ? C31A C32A C33A C34A 54.9(9) . . . . ? O3A C29A C34A C33A 175.7(5) . . . . ? O4A C29A C34A C33A -68.2(7) . . . . ? C30A C29A C34A C33A 52.4(8) . . . . ? C32A C33A C34A C29A -52.8(8) . . . . ? C40A C35A C36A C37A 1.0(15) . . . . ? C41A C35A C36A C37A -177.5(10) . . . . ? C35A C36A C37A C38A -3.1(18) . . . . ? C36A C37A C38A C39A 3(2) . . . . ? C37A C38A C39A C40A -1(2) . . . . ? C38A C39A C40A C35A -1.7(16) . . . . ? C36A C35A C40A C39A 1.5(13) . . . . ? C41A C35A C40A C39A 179.8(9) . . . . ? C36A C35A C41A O5A 11.6(14) . . . . ? C40A C35A C41A O5A -166.7(9) . . . . ? C36A C35A C41A C42A -159.9(9) . . . . ? C40A C35A C41A C42A 21.7(13) . . . . ? C47A N1A C42A O6A 0.3(16) . . . . ? C43A N1A C42A O6A 178.5(10) . . . . ? C47A N1A C42A C41A 175.9(11) . . . . ? C43A N1A C42A C41A -5.9(14) . . . . ? O5A C41A C42A O6A -91.0(11) . . . . ? C35A C41A C42A O6A 81.1(11) . . . . ? O5A C41A C42A N1A 93.0(11) . . . . ? C35A C41A C42A N1A -94.9(10) . . . . ? C42A N1A C43A C44A -126.6(13) . . . . ? C47A N1A C43A C44A 51.8(15) . . . . ? N1A C43A C44A C45A -54.3(16) . . . . ? C43A C44A C45A C46A 56.3(17) . . . . ? C44A C45A C46A C47A -57.4(17) . . . . ? C45A C46A C47A N1A 54.6(17) . . . . ? C42A N1A C47A C46A 127.9(13) . . . . ? C43A N1A C47A C46A -50.5(16) . . . . ? C29B O3B C1B C2B -146.3(5) . . . . ? C29B O3B C1B C15B -24.0(7) . . . . ? O3B C1B C2B O1B 176.0(5) . . . . ? C15B C1B C2B O1B 61.0(7) . . . . ? O3B C1B C2B C3B -69.6(7) . . . . ? C15B C1B C2B C3B 175.3(6) . . . . ? O3B C1B C2B C9B 57.2(7) . . . . ? C15B C1B C2B C9B -57.9(7) . . . . ? O1B C2B C3B C8B -54.6(8) . . . . ? C9B C2B C3B C8B 67.4(8) . . . . ? C1B C2B C3B C8B -164.7(6) . . . . ? O1B C2B C3B C4B 126.8(7) . . . . ? C9B C2B C3B C4B -111.1(8) . . . . ? C1B C2B C3B C4B 16.8(9) . . . . ? C8B C3B C4B C5B 0.7(11) . . . . ? C2B C3B C4B C5B 179.3(7) . . . . ? C3B C4B C5B C6B 1.0(12) . . . . ? C4B C5B C6B C7B -1.8(12) . . . . ? C5B C6B C7B C8B 0.8(12) . . . . ? C4B C3B C8B C7B -1.7(11) . . . . ? C2B C3B C8B C7B 179.7(7) . . . . ? C6B C7B C8B C3B 1.0(12) . . . . ? O1B C2B C9B C14B -8.8(9) . . . . ? C3B C2B C9B C14B -128.6(7) . . . . ? C1B C2B C9B C14B 103.7(7) . . . . ? O1B C2B C9B C10B 171.1(6) . . . . ? C3B C2B C9B C10B 51.3(8) . . . . ? C1B C2B C9B C10B -76.4(8) . . . . ? C14B C9B C10B C11B -0.5(11) . . . . ? C2B C9B C10B C11B 179.6(7) . . . . ? C9B C10B C11B C12B -1.8(15) . . . . ? C10B C11B C12B C13B 4.6(18) . . . . ? C11B C12B C13B C14B -5.5(18) . . . . ? C10B C9B C14B C13B -0.3(11) . . . . ? C2B C9B C14B C13B 179.6(7) . . . . ? C12B C13B C14B C9B 3.4(15) . . . . ? C29B O4B C15B C16B -131.2(5) . . . . ? C29B O4B C15B C1B -6.0(6) . . . . ? O3B C1B C15B O4B 17.7(6) . . . . ? C2B C1B C15B O4B 135.9(6) . . . . ? O3B C1B C15B C16B 138.5(6) . . . . ? C2B C1B C15B C16B -103.4(7) . . . . ? O4B C15B C16B O2B 179.3(5) . . . . ? C1B C15B C16B O2B 62.1(7) . . . . ? O4B C15B C16B C23B -65.9(7) . . . . ? C1B C15B C16B C23B 176.9(6) . . . . ? O4B C15B C16B C17B 58.4(7) . . . . ? C1B C15B C16B C17B -58.8(8) . . . . ? O2B C16B C17B C22B -25.7(8) . . . . ? C23B C16B C17B C22B -139.0(6) . . . . ? C15B C16B C17B C22B 95.5(7) . . . . ? O2B C16B C17B C18B 157.1(6) . . . . ? C23B C16B C17B C18B 43.7(8) . . . . ? C15B C16B C17B C18B -81.8(7) . . . . ? C22B C17B C18B C19B -0.3(9) . . . . ? C16B C17B C18B C19B 177.1(6) . . . . ? C17B C18B C19B C20B 1.9(11) . . . . ? C18B C19B C20B C21B -2.3(12) . . . . ? C19B C20B C21B C22B 1.0(13) . . . . ? C20B C21B C22B C17B 0.7(12) . . . . ? C18B C17B C22B C21B -1.0(10) . . . . ? C16B C17B C22B C21B -178.3(7) . . . . ? O2B C16B C23B C28B 123.2(8) . . . . ? C17B C16B C23B C28B -120.7(8) . . . . ? C15B C16B C23B C28B 5.4(10) . . . . ? O2B C16B C23B C24B -55.7(8) . . . . ? C17B C16B C23B C24B 60.5(8) . . . . ? C15B C16B C23B C24B -173.5(6) . . . . ? C28B C23B C24B C25B 0.9(12) . . . . ? C16B C23B C24B C25B 179.8(7) . . . . ? C23B C24B C25B C26B -2.0(14) . . . . ? C24B C25B C26B C27B 2.3(14) . . . . ? C25B C26B C27B C28B -1.6(13) . . . . ? C24B C23B C28B C27B -0.1(12) . . . . ? C16B C23B C28B C27B -179.0(7) . . . . ? C26B C27B C28B C23B 0.5(13) . . . . ? C1B O3B C29B O4B 20.9(7) . . . . ? C1B O3B C29B C34B 138.1(5) . . . . ? C1B O3B C29B C30B -100.2(6) . . . . ? C15B O4B C29B O3B -8.2(7) . . . . ? C15B O4B C29B C34B -124.1(6) . . . . ? C15B O4B C29B C30B 112.6(6) . . . . ? O3B C29B C30B C31B -67.1(7) . . . . ? O4B C29B C30B C31B 175.1(6) . . . . ? C34B C29B C30B C31B 52.6(8) . . . . ? C29B C30B C31B C32B -55.2(8) . . . . ? C30B C31B C32B C33B 58.4(8) . . . . ? C31B C32B C33B C34B -58.9(8) . . . . ? O3B C29B C34B C33B 68.4(7) . . . . ? O4B C29B C34B C33B -176.9(6) . . . . ? C30B C29B C34B C33B -53.3(8) . . . . ? C32B C33B C34B C29B 56.8(8) . . . . ? C40B C35B C36B C37B -4.3 . . . . ? C41B C35B C36B C37B -179.0 . . . . ? C35B C36B C37B C38B 4.3 . . . . ? C36B C37B C38B C39B -5.1 . . . . ? C37B C38B C39B C40B 5.2 . . . . ? C36B C35B C40B C39B 4.7 . . . . ? C41B C35B C40B C39B 178.5 . . . . ? C38B C39B C40B C35B -4.8 . . . . ? C40B C35B C41B O5B -166.0 . . . . ? C36B C35B C41B O5B 8.1 . . . . ? C40B C35B C41B C42B 21.9 . . . . ? C36B C35B C41B C42B -163.9 . . . . ? C43B N1B C42B O6B -165.9 . . . . ? C47B N1B C42B O6B -15.2 . . . . ? C43B N1B C42B C41B 15.6 . . . . ? C47B N1B C42B C41B 166.4 . . . . ? O5B C41B C42B O6B -88.0 . . . . ? C35B C41B C42B O6B 84.5 . . . . ? O5B C41B C42B N1B 90.4 . . . . ? C35B C41B C42B N1B -97.1 . . . . ? C42B N1B C43B C44B -138.3 . . . . ? C47B N1B C43B C44B 65.8 . . . . ? N1B C43B C44B C45B -58.8 . . . . ? C43B C44B C45B C46B 67.6 . . . . ? C44B C45B C46B C47B -77.7 . . . . ? C45B C46B C47B N1B 80.9 . . . . ? C42B N1B C47B C46B 124.7 . . . . ? C43B N1B C47B C46B -80.5 . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1A H1OA O2A 0.82 1.82 2.633(7) 173.9 . O2A H2OA O6A 0.82 1.95 2.686(7) 149.9 2_746 O1B H1OB O6B 0.82 1.98 2.709(16) 146.9 1_554 O2B H2OB O1B 0.82 1.84 2.644(6) 167.5 . _diffrn_measured_fraction_theta_max 0.954 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.954 _refine_diff_density_max 0.365 _refine_diff_density_min -0.304 _refine_diff_density_rms 0.076 # Attachment 'Vb.cif' data_g8br1 _database_code_depnum_ccdc_archive 'CCDC 666884' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H22 O2, C13 H15 N O2' _chemical_formula_sum 'C39 H37 N O4' _chemical_formula_weight 583.70 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.784(2) _cell_length_b 20.538(4) _cell_length_c 15.533(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.602(8) _cell_angle_gamma 90.00 _cell_volume 3068.2(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.264 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1240 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9806 _exptl_absorpt_correction_T_max 0.9922 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1998)' _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 'Bruker SMART 6K CCD Detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 8 _diffrn_standards_number none _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25341 _diffrn_reflns_av_R_equivalents 0.2150 _diffrn_reflns_av_sigmaI/netI 0.1821 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 25.05 _reflns_number_total 5436 _reflns_number_gt 1900 _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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.011(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5436 _refine_ls_number_parameters 387 _refine_ls_number_restraints 17 _refine_ls_R_factor_all 0.2813 _refine_ls_R_factor_gt 0.1192 _refine_ls_wR_factor_ref 0.3780 _refine_ls_wR_factor_gt 0.3100 _refine_ls_goodness_of_fit_ref 0.961 _refine_ls_restrained_S_all 0.970 _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 0.4012(5) 0.1059(2) 0.2151(3) 0.0439(13) Uani 1 1 d . . . H1O1 H 0.3763 0.1430 0.2242 0.066 Uiso 1 1 calc R . . O2 O 0.5583(5) -0.0229(2) 0.3570(3) 0.0498(14) Uani 1 1 d . . . H1O2 H 0.5859 -0.0599 0.3501 0.075 Uiso 1 1 calc R . . C1 C 0.4386(7) 0.0721(3) 0.2968(4) 0.0397(17) Uani 1 1 d . . . C2 C 0.3097(7) 0.0657(4) 0.3377(4) 0.0389(17) Uani 1 1 d . . . C3 C 0.2864(8) 0.0141(4) 0.3935(5) 0.056(2) Uani 1 1 d . . . H3 H 0.3500 -0.0199 0.4041 0.067 Uiso 1 1 calc R . . C4 C 0.1692(10) 0.0136(5) 0.4327(5) 0.070(3) Uani 1 1 d . . . H4 H 0.1555 -0.0208 0.4692 0.083 Uiso 1 1 calc R . . C5 C 0.0732(9) 0.0635(5) 0.4180(6) 0.063(2) Uani 1 1 d . . . H5 H -0.0042 0.0633 0.4449 0.076 Uiso 1 1 calc R . . C6 C 0.0937(9) 0.1134(5) 0.3632(6) 0.072(3) Uani 1 1 d . . . H6 H 0.0289 0.1468 0.3520 0.086 Uiso 1 1 calc R . . C7 C 0.2122(8) 0.1143(4) 0.3238(5) 0.053(2) Uani 1 1 d . . . H7 H 0.2246 0.1489 0.2873 0.063 Uiso 1 1 calc R . . C8 C 0.5501(7) 0.1106(3) 0.3585(4) 0.0375(17) Uani 1 1 d . . . C9 C 0.5571(7) 0.1114(4) 0.4487(4) 0.0480(19) Uani 1 1 d . . . H9 H 0.4944 0.0869 0.4735 0.058 Uiso 1 1 calc R . . C10 C 0.6564(8) 0.1483(4) 0.5015(5) 0.057(2) Uani 1 1 d . . . H10 H 0.6586 0.1492 0.5616 0.069 Uiso 1 1 calc R . . C11 C 0.7510(8) 0.1834(4) 0.4673(5) 0.0477(19) Uani 1 1 d . . . H11 H 0.8184 0.2073 0.5042 0.057 Uiso 1 1 calc R . . C12 C 0.7477(7) 0.1837(3) 0.3794(5) 0.0396(17) Uani 1 1 d . . . H12 H 0.8116 0.2085 0.3561 0.048 Uiso 1 1 calc R . . C13 C 0.6490(7) 0.1470(3) 0.3247(5) 0.0383(17) Uani 1 1 d . . . H13 H 0.6486 0.1466 0.2648 0.046 Uiso 1 1 calc R . . C14 C 0.5002(8) 0.0049(3) 0.2727(4) 0.0424(18) Uani 1 1 d . . . C15 C 0.3924(8) -0.0423(4) 0.2215(5) 0.0470(19) Uani 1 1 d . . . C16 C 0.2674(8) -0.0235(4) 0.1718(5) 0.049(2) Uani 1 1 d . . . H16 H 0.2411 0.0201 0.1707 0.059 Uiso 1 1 calc R . . C17 C 0.1814(9) -0.0683(5) 0.1237(5) 0.061(2) Uani 1 1 d . . . H17 H 0.0951 -0.0554 0.0926 0.073 Uiso 1 1 calc R . . C18 C 0.2225(10) -0.1325(4) 0.1211(6) 0.066(2) Uani 1 1 d . . . H18 H 0.1662 -0.1622 0.0859 0.079 Uiso 1 1 calc R . . C19 C 0.3445(10) -0.1520(4) 0.1699(7) 0.074(3) Uani 1 1 d . . . H19 H 0.3711 -0.1955 0.1704 0.089 Uiso 1 1 calc R . . C20 C 0.4281(9) -0.1070(4) 0.2183(6) 0.065(2) Uani 1 1 d . . . H20 H 0.5130 -0.1206 0.2505 0.078 Uiso 1 1 calc R . . C21 C 0.6179(7) 0.0141(3) 0.2203(5) 0.0404(18) Uani 1 1 d . . . C22 C 0.5852(8) 0.0286(3) 0.1304(5) 0.0473(19) Uani 1 1 d . . . H22 H 0.4926 0.0319 0.1031 0.057 Uiso 1 1 calc R . . C23 C 0.6896(9) 0.0380(4) 0.0817(5) 0.058(2) Uani 1 1 d . . . H23 H 0.6663 0.0474 0.0223 0.070 Uiso 1 1 calc R . . C24 C 0.8298(9) 0.0334(4) 0.1222(6) 0.064(2) Uani 1 1 d . . . H24 H 0.9002 0.0411 0.0906 0.077 Uiso 1 1 calc R . . C25 C 0.8609(9) 0.0171(4) 0.2097(6) 0.063(2) Uani 1 1 d . . . H25 H 0.9532 0.0112 0.2365 0.075 Uiso 1 1 calc R . . C26 C 0.7562(8) 0.0093(4) 0.2583(5) 0.0487(19) Uani 1 1 d . . . H26 H 0.7801 0.0006 0.3179 0.058 Uiso 1 1 calc R . . N1 N 0.3783(8) 0.2308(4) 0.0539(4) 0.097(3) Uiso 1 1 d D . . O3 O 0.2922(8) 0.3643(3) 0.0891(5) 0.109(2) Uiso 1 1 d . . . H1O3 H 0.2361 0.3869 0.0564 0.164 Uiso 1 1 calc RD . . O4 O 0.4171(7) 0.2427(3) 0.2002(5) 0.095(2) Uiso 1 1 d . . . C27 C 0.1132(10) 0.2928(6) 0.1268(7) 0.083(3) Uani 1 1 d D . . C28 C 0.0342(13) 0.3446(6) 0.1511(7) 0.093(3) Uani 1 1 d . . . H28 H 0.0626 0.3872 0.1443 0.112 Uiso 1 1 calc R . . C29 C -0.0836(12) 0.3335(5) 0.1844(6) 0.076(3) Uani 1 1 d . . . H29 H -0.1318 0.3685 0.2024 0.091 Uiso 1 1 calc R . . C30 C -0.1311(12) 0.2719(5) 0.1915(5) 0.082(3) Uani 1 1 d . . . H30 H -0.2130 0.2642 0.2122 0.098 Uiso 1 1 calc R . . C31 C -0.0534(13) 0.2204(5) 0.1669(6) 0.087(3) Uani 1 1 d . . . H31 H -0.0853 0.1781 0.1712 0.104 Uiso 1 1 calc R . . C32 C 0.0642(11) 0.2295(6) 0.1374(6) 0.082(3) Uani 1 1 d . . . H32 H 0.1145 0.1938 0.1237 0.098 Uiso 1 1 calc R . . C33 C 0.2481(10) 0.2976(4) 0.0816(5) 0.116(5) Uani 1 1 d D . . C34 C 0.3619(13) 0.2511(5) 0.1276(6) 0.117(5) Uani 1 1 d D . . C35 C 0.2718(10) 0.2663(4) -0.0046(6) 0.124(5) Uani 1 1 d D . . H35 H 0.3107 0.2970 -0.0419 0.35(13) Uiso 1 1 calc R . . C36 C 0.1695(7) 0.2191(4) -0.0571(7) 0.136(5) Uani 1 1 d D . . H36A H 0.1028 0.2429 -0.0996 0.163 Uiso 1 1 calc R . . H36B H 0.1190 0.1961 -0.0183 0.163 Uiso 1 1 calc R . . C37 C 0.2476(11) 0.1705(4) -0.1042(5) 0.137(6) Uani 1 1 d D . . H37A H 0.1825 0.1396 -0.1364 0.164 Uiso 1 1 calc R . . H37B H 0.2932 0.1933 -0.1457 0.164 Uiso 1 1 calc R . . C38 C 0.3554(10) 0.1344(4) -0.0384(7) 0.128(5) Uani 1 1 d D . . H38A H 0.3085 0.1079 -0.0011 0.154 Uiso 1 1 calc R . . H38B H 0.4081 0.1055 -0.0695 0.154 Uiso 1 1 calc R . . C39 C 0.4536(8) 0.1807(4) 0.0175(6) 0.118(4) Uani 1 1 d D . . H39A H 0.5109 0.1567 0.0646 0.142 Uiso 1 1 calc R . . H39B H 0.5145 0.2005 -0.0178 0.142 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 0.063(3) 0.036(3) 0.032(3) 0.006(2) 0.009(2) 0.010(3) O2 0.068(3) 0.042(3) 0.042(3) 0.009(2) 0.015(3) 0.015(3) C1 0.051(4) 0.039(4) 0.030(4) 0.007(3) 0.008(3) 0.008(3) C2 0.039(4) 0.051(5) 0.026(3) -0.005(3) 0.005(3) 0.001(3) C3 0.058(5) 0.061(5) 0.049(5) 0.010(4) 0.010(4) 0.007(4) C4 0.088(7) 0.082(7) 0.047(5) -0.004(5) 0.035(5) -0.029(6) C5 0.047(5) 0.079(7) 0.069(6) -0.022(5) 0.027(4) -0.007(5) C6 0.063(6) 0.068(6) 0.087(7) -0.007(5) 0.020(5) 0.021(5) C7 0.053(5) 0.055(5) 0.052(5) -0.007(4) 0.016(4) -0.002(4) C8 0.044(4) 0.033(4) 0.035(4) 0.004(3) 0.006(3) 0.001(3) C9 0.046(4) 0.058(5) 0.037(4) 0.009(4) 0.000(3) -0.015(4) C10 0.065(5) 0.069(6) 0.036(4) 0.011(4) 0.003(4) -0.016(5) C11 0.051(5) 0.049(5) 0.039(4) 0.001(4) -0.001(4) 0.001(4) C12 0.032(4) 0.029(4) 0.057(5) 0.010(3) 0.008(3) -0.002(3) C13 0.042(4) 0.029(4) 0.044(4) 0.003(3) 0.009(3) 0.007(3) C14 0.055(5) 0.039(4) 0.034(4) 0.011(3) 0.010(4) 0.011(4) C15 0.048(5) 0.048(5) 0.049(4) -0.002(4) 0.020(4) -0.005(4) C16 0.065(5) 0.045(5) 0.039(4) -0.002(4) 0.015(4) -0.008(4) C17 0.057(5) 0.083(7) 0.048(5) 0.000(5) 0.021(4) 0.001(5) C18 0.077(7) 0.062(6) 0.066(6) -0.013(5) 0.029(5) -0.023(5) C19 0.068(6) 0.048(5) 0.109(8) -0.016(5) 0.022(6) -0.018(5) C20 0.070(6) 0.034(5) 0.095(7) 0.000(5) 0.028(5) -0.003(4) C21 0.045(5) 0.028(4) 0.051(4) -0.013(3) 0.016(4) -0.007(3) C22 0.055(5) 0.043(4) 0.043(4) -0.007(4) 0.008(4) -0.003(4) C23 0.066(6) 0.063(6) 0.051(5) -0.010(4) 0.023(4) -0.011(4) C24 0.067(6) 0.072(6) 0.059(5) -0.021(5) 0.023(5) -0.006(5) C25 0.050(5) 0.066(6) 0.071(6) -0.004(5) 0.011(5) 0.003(4) C26 0.054(5) 0.047(5) 0.046(4) -0.010(4) 0.011(4) 0.003(4) C27 0.064(6) 0.092(8) 0.082(7) 0.019(6) -0.018(5) -0.004(6) C28 0.100(9) 0.082(8) 0.080(7) 0.015(6) -0.028(7) -0.009(7) C29 0.096(8) 0.078(8) 0.049(5) -0.005(5) 0.001(5) 0.012(6) C30 0.123(9) 0.080(7) 0.046(5) 0.030(5) 0.025(5) 0.014(7) C31 0.123(10) 0.066(7) 0.069(6) 0.019(6) 0.009(6) 0.012(7) C32 0.077(7) 0.097(8) 0.066(6) 0.028(6) 0.000(5) 0.003(6) C33 0.126(10) 0.042(6) 0.163(12) 0.034(7) -0.015(9) -0.026(6) C34 0.192(12) 0.129(10) 0.025(5) -0.010(5) 0.010(6) 0.067(9) C35 0.122(10) 0.129(11) 0.112(10) -0.079(9) -0.001(8) -0.005(9) C36 0.083(8) 0.072(8) 0.229(16) -0.024(9) -0.036(9) 0.001(7) C37 0.192(14) 0.094(9) 0.089(8) -0.029(7) -0.069(9) 0.038(10) C38 0.163(13) 0.086(9) 0.134(11) -0.036(9) 0.025(10) 0.004(9) C39 0.161(12) 0.085(8) 0.115(10) -0.018(7) 0.041(9) 0.011(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.434(7) . ? O1 H1O1 0.8200 . ? O2 C14 1.446(8) . ? O2 H1O2 0.8200 . ? C1 C2 1.518(9) . ? C1 C8 1.532(9) . ? C1 C14 1.578(9) . ? C2 C7 1.371(10) . ? C2 C3 1.414(10) . ? C3 C4 1.394(11) . ? C3 H3 0.9300 . ? C4 C5 1.381(12) . ? C4 H4 0.9300 . ? C5 C6 1.369(12) . ? C5 H5 0.9300 . ? C6 C7 1.407(11) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C9 1.391(9) . ? C8 C13 1.400(9) . ? C9 C10 1.379(10) . ? C9 H9 0.9300 . ? C10 C11 1.355(10) . ? C10 H10 0.9300 . ? C11 C12 1.360(9) . ? C11 H11 0.9300 . ? C12 C13 1.386(9) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C21 1.538(10) . ? C14 C15 1.543(10) . ? C15 C16 1.376(10) . ? C15 C20 1.377(10) . ? C16 C17 1.373(11) . ? C16 H16 0.9300 . ? C17 C18 1.380(12) . ? C17 H17 0.9300 . ? C18 C19 1.352(13) . ? C18 H18 0.9300 . ? C19 C20 1.365(11) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 C26 1.376(10) . ? C21 C22 1.406(10) . ? C22 C23 1.392(10) . ? C22 H22 0.9300 . ? C23 C24 1.403(11) . ? C23 H23 0.9300 . ? C24 C25 1.378(12) . ? C24 H24 0.9300 . ? C25 C26 1.390(10) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? N1 C34 1.255(10) . ? N1 C39 1.442(5) . ? N1 C35 1.448(5) . ? O3 C33 1.434(10) . ? O3 H1O3 0.8200 . ? O4 C34 1.170(10) . ? C27 C32 1.405(13) . ? C27 C28 1.407(14) . ? C27 C33 1.609(13) . ? C28 C29 1.367(14) . ? C28 H28 0.9300 . ? C29 C30 1.360(13) . ? C29 H29 0.9300 . ? C30 C31 1.396(13) . ? C30 H30 0.9300 . ? C31 C32 1.328(13) . ? C31 H31 0.9300 . ? C32 H32 0.9300 . ? C33 C34 1.5397(11) . ? C33 C35 1.5404(11) . ? C35 C36 1.519(5) . ? C35 H35 0.9800 . ? C36 C37 1.523(5) . ? C36 H36A 0.9700 . ? C36 H36B 0.9700 . ? C37 C38 1.520(5) . ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? C38 C39 1.509(5) . ? C38 H38A 0.9700 . ? C38 H38B 0.9700 . ? C39 H39A 0.9700 . ? C39 H39B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1O1 109.5 . . ? C14 O2 H1O2 109.5 . . ? O1 C1 C2 108.4(5) . . ? O1 C1 C8 109.8(5) . . ? C2 C1 C8 109.5(5) . . ? O1 C1 C14 105.1(5) . . ? C2 C1 C14 114.0(6) . . ? C8 C1 C14 109.9(5) . . ? C7 C2 C3 117.1(7) . . ? C7 C2 C1 118.6(6) . . ? C3 C2 C1 124.2(7) . . ? C4 C3 C2 120.8(8) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C5 C4 C3 120.8(8) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C6 C5 C4 119.0(8) . . ? C6 C5 H5 120.5 . . ? C4 C5 H5 120.5 . . ? C5 C6 C7 120.5(8) . . ? C5 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? C2 C7 C6 121.8(8) . . ? C2 C7 H7 119.1 . . ? C6 C7 H7 119.1 . . ? C9 C8 C13 117.5(6) . . ? C9 C8 C1 122.2(6) . . ? C13 C8 C1 120.3(6) . . ? C10 C9 C8 120.3(7) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C11 C10 C9 121.1(7) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? C10 C11 C12 120.3(7) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C11 C12 C13 119.9(7) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C12 C13 C8 120.8(6) . . ? C12 C13 H13 119.6 . . ? C8 C13 H13 119.6 . . ? O2 C14 C21 108.7(6) . . ? O2 C14 C15 109.6(6) . . ? C21 C14 C15 108.2(5) . . ? O2 C14 C1 103.5(5) . . ? C21 C14 C1 112.0(6) . . ? C15 C14 C1 114.7(6) . . ? C16 C15 C20 117.2(7) . . ? C16 C15 C14 124.4(7) . . ? C20 C15 C14 118.1(7) . . ? C15 C16 C17 120.6(8) . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? C18 C17 C16 120.2(8) . . ? C18 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C19 C18 C17 120.0(9) . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C18 C19 C20 119.0(9) . . ? C18 C19 H19 120.5 . . ? C20 C19 H19 120.5 . . ? C19 C20 C15 122.9(9) . . ? C19 C20 H20 118.6 . . ? C15 C20 H20 118.6 . . ? C26 C21 C22 117.8(7) . . ? C26 C21 C14 122.5(7) . . ? C22 C21 C14 119.7(7) . . ? C23 C22 C21 120.9(7) . . ? C23 C22 H22 119.5 . . ? C21 C22 H22 119.5 . . ? C22 C23 C24 120.1(8) . . ? C22 C23 H23 119.9 . . ? C24 C23 H23 119.9 . . ? C25 C24 C23 118.6(8) . . ? C25 C24 H24 120.7 . . ? C23 C24 H24 120.7 . . ? C24 C25 C26 120.8(8) . . ? C24 C25 H25 119.6 . . ? C26 C25 H25 119.6 . . ? C21 C26 C25 121.6(7) . . ? C21 C26 H26 119.2 . . ? C25 C26 H26 119.2 . . ? C34 N1 C39 139.0(7) . . ? C34 N1 C35 102.0(7) . . ? C39 N1 C35 118.3(5) . . ? C33 O3 H1O3 109.5 . . ? C32 C27 C28 116.9(10) . . ? C32 C27 C33 115.6(10) . . ? C28 C27 C33 127.3(10) . . ? C29 C28 C27 121.2(10) . . ? C29 C28 H28 119.4 . . ? C27 C28 H28 119.4 . . ? C30 C29 C28 120.7(10) . . ? C30 C29 H29 119.7 . . ? C28 C29 H29 119.7 . . ? C29 C30 C31 118.2(10) . . ? C29 C30 H30 120.9 . . ? C31 C30 H30 120.9 . . ? C32 C31 C30 122.5(11) . . ? C32 C31 H31 118.8 . . ? C30 C31 H31 118.8 . . ? C31 C32 C27 120.5(11) . . ? C31 C32 H32 119.8 . . ? C27 C32 H32 119.8 . . ? O3 C33 C34 112.0(7) . . ? O3 C33 C35 112.2(7) . . ? C34 C33 C35 86.2(6) . . ? O3 C33 C27 106.4(7) . . ? C34 C33 C27 109.9(8) . . ? C35 C33 C27 128.3(9) . . ? O4 C34 N1 135.7(9) . . ? O4 C34 C33 134.8(8) . . ? N1 C34 C33 89.1(7) . . ? N1 C35 C36 110.0(5) . . ? N1 C35 C33 82.5(6) . . ? C36 C35 C33 123.0(9) . . ? N1 C35 H35 112.5 . . ? C36 C35 H35 112.5 . . ? C33 C35 H35 112.5 . . ? C35 C36 C37 109.7(4) . . ? C35 C36 H36A 109.7 . . ? C37 C36 H36A 109.7 . . ? C35 C36 H36B 109.7 . . ? C37 C36 H36B 109.7 . . ? H36A C36 H36B 108.2 . . ? C38 C37 C36 110.2(4) . . ? C38 C37 H37A 109.6 . . ? C36 C37 H37A 109.6 . . ? C38 C37 H37B 109.6 . . ? C36 C37 H37B 109.6 . . ? H37A C37 H37B 108.1 . . ? C39 C38 C37 111.6(4) . . ? C39 C38 H38A 109.3 . . ? C37 C38 H38A 109.3 . . ? C39 C38 H38B 109.3 . . ? C37 C38 H38B 109.3 . . ? H38A C38 H38B 108.0 . . ? N1 C39 C38 111.0(4) . . ? N1 C39 H39A 109.4 . . ? C38 C39 H39A 109.4 . . ? N1 C39 H39B 109.4 . . ? C38 C39 H39B 109.4 . . ? H39A C39 H39B 108.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C7 -32.8(8) . . . . ? C8 C1 C2 C7 87.0(7) . . . . ? C14 C1 C2 C7 -149.4(6) . . . . ? O1 C1 C2 C3 150.7(6) . . . . ? C8 C1 C2 C3 -89.5(8) . . . . ? C14 C1 C2 C3 34.1(9) . . . . ? C7 C2 C3 C4 -0.4(11) . . . . ? C1 C2 C3 C4 176.1(7) . . . . ? C2 C3 C4 C5 -0.1(12) . . . . ? C3 C4 C5 C6 0.8(13) . . . . ? C4 C5 C6 C7 -1.1(13) . . . . ? C3 C2 C7 C6 0.1(11) . . . . ? C1 C2 C7 C6 -176.6(7) . . . . ? C5 C6 C7 C2 0.7(13) . . . . ? O1 C1 C8 C9 146.3(6) . . . . ? C2 C1 C8 C9 27.4(9) . . . . ? C14 C1 C8 C9 -98.6(7) . . . . ? O1 C1 C8 C13 -33.2(8) . . . . ? C2 C1 C8 C13 -152.1(6) . . . . ? C14 C1 C8 C13 81.9(7) . . . . ? C13 C8 C9 C10 1.6(11) . . . . ? C1 C8 C9 C10 -177.9(7) . . . . ? C8 C9 C10 C11 -1.5(12) . . . . ? C9 C10 C11 C12 1.3(12) . . . . ? C10 C11 C12 C13 -1.3(11) . . . . ? C11 C12 C13 C8 1.5(10) . . . . ? C9 C8 C13 C12 -1.6(9) . . . . ? C1 C8 C13 C12 177.9(6) . . . . ? O1 C1 C14 O2 170.6(5) . . . . ? C2 C1 C14 O2 -70.9(7) . . . . ? C8 C1 C14 O2 52.4(7) . . . . ? O1 C1 C14 C21 53.7(7) . . . . ? C2 C1 C14 C21 172.2(6) . . . . ? C8 C1 C14 C21 -64.4(7) . . . . ? O1 C1 C14 C15 -70.1(7) . . . . ? C2 C1 C14 C15 48.4(7) . . . . ? C8 C1 C14 C15 171.8(5) . . . . ? O2 C14 C15 C16 139.5(7) . . . . ? C21 C14 C15 C16 -102.2(8) . . . . ? C1 C14 C15 C16 23.6(9) . . . . ? O2 C14 C15 C20 -47.0(9) . . . . ? C21 C14 C15 C20 71.4(8) . . . . ? C1 C14 C15 C20 -162.9(6) . . . . ? C20 C15 C16 C17 2.1(10) . . . . ? C14 C15 C16 C17 175.7(6) . . . . ? C15 C16 C17 C18 -3.3(11) . . . . ? C16 C17 C18 C19 3.6(12) . . . . ? C17 C18 C19 C20 -2.7(13) . . . . ? C18 C19 C20 C15 1.6(14) . . . . ? C16 C15 C20 C19 -1.2(12) . . . . ? C14 C15 C20 C19 -175.3(7) . . . . ? O2 C14 C21 C26 -12.8(9) . . . . ? C15 C14 C21 C26 -131.7(7) . . . . ? C1 C14 C21 C26 101.0(7) . . . . ? O2 C14 C21 C22 167.8(6) . . . . ? C15 C14 C21 C22 48.9(8) . . . . ? C1 C14 C21 C22 -78.5(8) . . . . ? C26 C21 C22 C23 -0.3(10) . . . . ? C14 C21 C22 C23 179.2(6) . . . . ? C21 C22 C23 C24 -0.2(11) . . . . ? C22 C23 C24 C25 2.3(12) . . . . ? C23 C24 C25 C26 -3.9(12) . . . . ? C22 C21 C26 C25 -1.2(10) . . . . ? C14 C21 C26 C25 179.3(7) . . . . ? C24 C25 C26 C21 3.4(12) . . . . ? C32 C27 C28 C29 0.8(14) . . . . ? C33 C27 C28 C29 176.1(8) . . . . ? C27 C28 C29 C30 -2.9(15) . . . . ? C28 C29 C30 C31 2.3(14) . . . . ? C29 C30 C31 C32 0.3(15) . . . . ? C30 C31 C32 C27 -2.3(15) . . . . ? C28 C27 C32 C31 1.7(14) . . . . ? C33 C27 C32 C31 -174.1(8) . . . . ? C32 C27 C33 O3 -171.6(7) . . . . ? C28 C27 C33 O3 13.1(12) . . . . ? C32 C27 C33 C34 -50.1(10) . . . . ? C28 C27 C33 C34 134.6(10) . . . . ? C32 C27 C33 C35 51.1(11) . . . . ? C28 C27 C33 C35 -124.1(11) . . . . ? C39 N1 C34 O4 13(3) . . . . ? C35 N1 C34 O4 -177.4(16) . . . . ? C39 N1 C34 C33 -172.9(11) . . . . ? C35 N1 C34 C33 -3.2(9) . . . . ? O3 C33 C34 O4 64.8(18) . . . . ? C35 C33 C34 O4 177.2(17) . . . . ? C27 C33 C34 O4 -53.2(19) . . . . ? O3 C33 C34 N1 -109.4(9) . . . . ? C35 C33 C34 N1 3.0(8) . . . . ? C27 C33 C34 N1 132.5(9) . . . . ? C34 N1 C35 C36 -119.2(10) . . . . ? C39 N1 C35 C36 53.2(10) . . . . ? C34 N1 C35 C33 3.3(9) . . . . ? C39 N1 C35 C33 175.6(8) . . . . ? O3 C33 C35 N1 109.6(7) . . . . ? C34 C33 C35 N1 -2.6(7) . . . . ? C27 C33 C35 N1 -115.1(9) . . . . ? O3 C33 C35 C36 -141.3(7) . . . . ? C34 C33 C35 C36 106.5(8) . . . . ? C27 C33 C35 C36 -6.0(11) . . . . ? N1 C35 C36 C37 -54.7(9) . . . . ? C33 C35 C36 C37 -148.8(8) . . . . ? C35 C36 C37 C38 57.7(9) . . . . ? C36 C37 C38 C39 -55.6(10) . . . . ? C34 N1 C39 C38 118.1(14) . . . . ? C35 N1 C39 C38 -50.4(10) . . . . ? C37 C38 C39 N1 49.9(10) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.687 _refine_diff_density_min -0.663 _refine_diff_density_rms 0.094