# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_ack2_m _database_code_depnum_ccdc_archive 'CCDC 771919' #TrackingRef '2aA-acta.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; 'TADDOL FORM A' ; _chemical_name_common "'TADDOL FORM A'" _chemical_melting_point ? _chemical_formula_moiety 'C21 H26 O4' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C21 H26 O4' _chemical_formula_iupac ? _chemical_formula_weight 342.42 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,-y,1/2+z 3 1/2+x,1/2-y,-z 4 -x,1/2+y,1/2-z _cell_length_a 8.5968(8) _cell_length_b 9.7560(9) _cell_length_c 23.391(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1961.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(1) _cell_measurement_reflns_used 3845 _cell_measurement_theta_min 1.7 _cell_measurement_theta_max 26.00 _cell_special_details ; ; _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.159 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9767 _exptl_absorpt_correction_T_max 0.9844 _exptl_absorpt_process_details 'Apex2 (Bruker)' _exptl_crystal_density_meas_temp ? #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 293(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Brucker kappa apex2 CCD area detector' _diffrn_measurement_method '\f and \w scans' _chemical_absolute_configuration unk _diffrn_reflns_number 15354 _diffrn_reflns_av_R_equivalents 0.0336 _diffrn_reflns_av_sigmaI/netI 0.0322 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 26.00 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 3845 # number of observed reflections (> n sig(I)) _reflns_number_gt 3220 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker kappa Apex2' _computing_cell_refinement Apex2 _computing_data_reduction SAINT32 _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'WinGX (Farrugia, 1999)' #=============================================================================== # 8. REFINEMENT DATA _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^)+(0.0497P)^2^+0.1559P] 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 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.2(13) _refine_ls_number_reflns 3845 _refine_ls_number_parameters 232 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0664 _refine_ls_R_factor_gt 0.0526 _refine_ls_wR_factor_ref 0.1115 _refine_ls_wR_factor_gt 0.1068 _refine_ls_goodness_of_fit_ref 1.150 _refine_ls_restrained_S_all 1.150 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.158 _refine_diff_density_min -0.227 _refine_diff_density_rms 0.047 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 O4 O 0.95063(19) 0.40166(14) 0.20730(5) 0.0451(4) Uani 1 1 d . . . H4 H 0.9757 0.3346 0.2263 0.068 Uiso 1 1 calc R . . O3 O 0.98248(18) 0.68009(15) 0.21758(6) 0.0445(4) Uani 1 1 d . . . H3 H 0.9707 0.5974 0.2223 0.067 Uiso 1 1 calc R . . O2 O 0.82961(17) 0.45232(14) 0.06171(5) 0.0433(4) Uani 1 1 d . . . O1 O 0.8602(2) 0.68275(14) 0.06884(6) 0.0529(4) Uani 1 1 d . . . C2 C 0.9256(2) 0.62565(19) 0.11921(8) 0.0369(5) Uani 1 1 d . . . H2 H 1.0384 0.6174 0.1143 0.044 Uiso 1 1 calc R . . C8 C 0.9477(2) 0.3654(2) 0.14786(8) 0.0368(5) Uani 1 1 d . . . C3 C 0.8542(2) 0.48272(19) 0.12060(8) 0.0332(4) Uani 1 1 d . . . H3A H 0.7528 0.4882 0.1396 0.040 Uiso 1 1 calc R . . C10 C 0.7201(3) 0.7309(2) 0.18515(8) 0.0471(6) Uani 1 1 d . . . C6 C 0.8919(2) 0.7242(2) 0.16958(8) 0.0393(5) Uani 1 1 d . . . C16 C 1.1121(2) 0.3538(2) 0.12431(8) 0.0410(5) Uani 1 1 d . . . C17 C 1.2378(3) 0.4075(3) 0.15318(11) 0.0628(7) Uani 1 1 d . . . H17 H 1.2222 0.4501 0.1883 0.075 Uiso 1 1 calc R . . C1 C 0.8405(3) 0.5743(2) 0.02890(8) 0.0561(6) Uani 1 1 d . . . C11 C 0.6607(3) 0.6611(3) 0.23135(11) 0.0643(7) Uani 1 1 d . . . H11 H 0.7269 0.6081 0.2537 0.077 Uiso 1 1 calc R . . C9 C 0.8574(3) 0.2329(2) 0.14146(10) 0.0568(6) Uani 1 1 d . . . H9C H 0.9131 0.1599 0.1599 0.085 Uiso 1 1 calc R . . H9B H 0.8451 0.2120 0.1016 0.085 Uiso 1 1 calc R . . H9A H 0.7569 0.2428 0.1588 0.085 Uiso 1 1 calc R . . C7 C 0.9569(3) 0.8652(2) 0.15446(11) 0.0626(7) Uani 1 1 d . . . H7C H 0.9401 0.9269 0.1858 0.094 Uiso 1 1 calc R . . H7A H 0.9051 0.8995 0.1210 0.094 Uiso 1 1 calc R . . H7B H 1.0664 0.8578 0.1470 0.094 Uiso 1 1 calc R . . C21 C 1.1411(3) 0.2900(3) 0.07245(10) 0.0615(7) Uani 1 1 d . . . H21 H 1.0589 0.2514 0.0522 0.074 Uiso 1 1 calc R . . C15 C 0.6167(3) 0.8078(4) 0.15331(11) 0.0826(10) Uani 1 1 d . . . H15 H 0.6524 0.8560 0.1216 0.099 Uiso 1 1 calc R . . C4 C 0.9821(5) 0.5646(3) -0.00937(12) 0.1028(13) Uani 1 1 d . . . H4C H 1.0738 0.5557 0.0137 0.154 Uiso 1 1 calc R . . H4B H 0.9897 0.6460 -0.0323 0.154 Uiso 1 1 calc R . . H4A H 0.9725 0.4861 -0.0339 0.154 Uiso 1 1 calc R . . C20 C 1.2897(4) 0.2826(3) 0.05022(12) 0.0793(9) Uani 1 1 d . . . H20 H 1.3063 0.2404 0.0151 0.095 Uiso 1 1 calc R . . C18 C 1.3856(3) 0.3995(4) 0.13114(14) 0.0876(10) Uani 1 1 d . . . H18 H 1.4684 0.4368 0.1514 0.105 Uiso 1 1 calc R . . C5 C 0.6910(5) 0.5976(3) -0.00301(14) 0.1139(15) Uani 1 1 d . . . H5A H 0.6734 0.5229 -0.0289 0.171 Uiso 1 1 calc R . . H5C H 0.6978 0.6817 -0.0242 0.171 Uiso 1 1 calc R . . H5B H 0.6064 0.6031 0.0237 0.171 Uiso 1 1 calc R . . C12 C 0.5043(4) 0.6683(4) 0.24525(15) 0.0868(10) Uani 1 1 d . . . H12 H 0.4671 0.6206 0.2768 0.104 Uiso 1 1 calc R . . C19 C 1.4125(4) 0.3371(4) 0.07953(15) 0.0880(10) Uani 1 1 d . . . H19 H 1.5127 0.3319 0.0647 0.106 Uiso 1 1 calc R . . C14 C 0.4619(4) 0.8142(5) 0.16767(14) 0.1079(15) Uani 1 1 d . . . H14 H 0.3950 0.8674 0.1457 0.129 Uiso 1 1 calc R . . C13 C 0.4047(4) 0.7445(5) 0.21319(14) 0.0981(12) Uani 1 1 d . . . H13 H 0.2995 0.7488 0.2223 0.118 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 O4 0.0685(10) 0.0377(8) 0.0292(7) 0.0065(6) -0.0021(7) 0.0094(7) O3 0.0565(9) 0.0381(8) 0.0389(7) -0.0040(6) -0.0137(7) 0.0020(7) O2 0.0618(9) 0.0375(7) 0.0305(7) -0.0019(6) -0.0095(7) 0.0008(7) O1 0.0955(12) 0.0336(8) 0.0296(7) 0.0031(6) -0.0058(8) 0.0046(8) C2 0.0455(12) 0.0334(11) 0.0318(9) 0.0023(8) 0.0026(9) 0.0027(9) C8 0.0493(12) 0.0306(10) 0.0304(9) -0.0009(8) -0.0022(9) 0.0015(10) C3 0.0361(11) 0.0356(11) 0.0279(9) -0.0039(8) 0.0009(8) -0.0006(9) C10 0.0577(15) 0.0484(13) 0.0352(10) -0.0137(10) -0.0047(10) 0.0147(11) C6 0.0540(14) 0.0307(10) 0.0333(10) -0.0023(8) -0.0076(9) 0.0037(9) C16 0.0468(13) 0.0359(11) 0.0401(10) -0.0041(9) -0.0041(9) 0.0096(10) C17 0.0518(16) 0.0735(18) 0.0632(14) -0.0236(14) -0.0001(12) 0.0044(13) C1 0.0972(19) 0.0406(12) 0.0303(10) 0.0014(9) -0.0112(12) 0.0041(13) C11 0.0614(17) 0.0704(17) 0.0610(15) 0.0017(13) 0.0076(13) 0.0191(15) C9 0.0753(17) 0.0379(12) 0.0572(13) 0.0063(10) -0.0028(12) -0.0065(12) C7 0.098(2) 0.0332(12) 0.0566(14) -0.0022(10) -0.0123(14) -0.0013(13) C21 0.0582(16) 0.0692(17) 0.0570(14) -0.0204(12) -0.0027(12) 0.0139(13) C15 0.077(2) 0.119(3) 0.0516(14) 0.0040(16) -0.0054(14) 0.0401(19) C4 0.178(4) 0.0675(19) 0.0631(17) -0.0096(16) 0.054(2) -0.028(2) C20 0.073(2) 0.095(2) 0.0700(17) -0.0280(17) 0.0121(15) 0.0237(18) C18 0.0498(17) 0.114(3) 0.099(2) -0.039(2) -0.0042(15) 0.0019(17) C5 0.177(4) 0.075(2) 0.089(2) -0.0050(18) -0.078(3) 0.029(2) C12 0.073(2) 0.109(3) 0.0784(19) -0.0079(19) 0.0213(16) 0.011(2) C19 0.0586(18) 0.104(3) 0.102(2) -0.017(2) 0.0178(17) 0.0191(18) C14 0.077(2) 0.175(4) 0.071(2) -0.009(2) -0.0108(18) 0.062(2) C13 0.0607(19) 0.154(3) 0.080(2) -0.036(2) 0.0008(17) 0.031(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 O4 C8 1.435(2) . ? O4 H4 0.8200 . ? O3 C6 1.433(2) . ? O3 H3 0.8200 . ? O2 C1 1.419(3) . ? O2 C3 1.425(2) . ? O1 C2 1.419(2) . ? O1 C1 1.422(2) . ? C2 C3 1.524(3) . ? C2 C6 1.548(3) . ? C2 H2 0.9800 . ? C8 C9 1.515(3) . ? C8 C16 1.521(3) . ? C8 C3 1.537(3) . ? C3 H3A 0.9800 . ? C10 C11 1.376(3) . ? C10 C15 1.381(3) . ? C10 C6 1.522(3) . ? C6 C7 1.526(3) . ? C16 C17 1.378(3) . ? C16 C21 1.386(3) . ? C17 C18 1.374(4) . ? C17 H17 0.9300 . ? C1 C5 1.503(4) . ? C1 C4 1.514(4) . ? C11 C12 1.385(4) . ? C11 H11 0.9300 . ? C9 H9C 0.9600 . ? C9 H9B 0.9600 . ? C9 H9A 0.9600 . ? C7 H7C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C21 C20 1.381(4) . ? C21 H21 0.9300 . ? C15 C14 1.374(4) . ? C15 H15 0.9300 . ? C4 H4C 0.9600 . ? C4 H4B 0.9600 . ? C4 H4A 0.9600 . ? C20 C19 1.366(4) . ? C20 H20 0.9300 . ? C18 C19 1.372(4) . ? C18 H18 0.9300 . ? C5 H5A 0.9600 . ? C5 H5C 0.9600 . ? C5 H5B 0.9600 . ? C12 C13 1.360(5) . ? C12 H12 0.9300 . ? C19 H19 0.9300 . ? C14 C13 1.356(5) . ? C14 H14 0.9300 . ? C13 H13 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 O4 H4 109.5 . . ? C6 O3 H3 109.5 . . ? C1 O2 C3 109.80(14) . . ? C2 O1 C1 107.49(14) . . ? O1 C2 C3 102.57(15) . . ? O1 C2 C6 108.29(15) . . ? C3 C2 C6 118.47(16) . . ? O1 C2 H2 109.0 . . ? C3 C2 H2 109.0 . . ? C6 C2 H2 109.0 . . ? O4 C8 C9 108.37(17) . . ? O4 C8 C16 110.66(17) . . ? C9 C8 C16 112.12(18) . . ? O4 C8 C3 103.15(15) . . ? C9 C8 C3 109.07(17) . . ? C16 C8 C3 113.01(16) . . ? O2 C3 C2 103.27(15) . . ? O2 C3 C8 108.88(15) . . ? C2 C3 C8 118.68(16) . . ? O2 C3 H3A 108.5 . . ? C2 C3 H3A 108.5 . . ? C8 C3 H3A 108.5 . . ? C11 C10 C15 117.0(2) . . ? C11 C10 C6 121.8(2) . . ? C15 C10 C6 121.3(2) . . ? O3 C6 C10 110.66(16) . . ? O3 C6 C7 104.66(18) . . ? C10 C6 C7 111.85(19) . . ? O3 C6 C2 107.93(15) . . ? C10 C6 C2 112.98(17) . . ? C7 C6 C2 108.34(17) . . ? C17 C16 C21 117.3(2) . . ? C17 C16 C8 121.52(18) . . ? C21 C16 C8 121.16(19) . . ? C18 C17 C16 121.3(2) . . ? C18 C17 H17 119.3 . . ? C16 C17 H17 119.3 . . ? O2 C1 O1 106.05(14) . . ? O2 C1 C5 109.8(2) . . ? O1 C1 C5 108.4(2) . . ? O2 C1 C4 108.7(2) . . ? O1 C1 C4 109.8(2) . . ? C5 C1 C4 113.8(2) . . ? C10 C11 C12 121.3(3) . . ? C10 C11 H11 119.3 . . ? C12 C11 H11 119.3 . . ? C8 C9 H9C 109.5 . . ? C8 C9 H9B 109.5 . . ? H9C C9 H9B 109.5 . . ? C8 C9 H9A 109.5 . . ? H9C C9 H9A 109.5 . . ? H9B C9 H9A 109.5 . . ? C6 C7 H7C 109.5 . . ? C6 C7 H7A 109.5 . . ? H7C C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7C C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C20 C21 C16 121.3(2) . . ? C20 C21 H21 119.4 . . ? C16 C21 H21 119.4 . . ? C14 C15 C10 121.1(3) . . ? C14 C15 H15 119.4 . . ? C10 C15 H15 119.4 . . ? C1 C4 H4C 109.5 . . ? C1 C4 H4B 109.5 . . ? H4C C4 H4B 109.5 . . ? C1 C4 H4A 109.5 . . ? H4C C4 H4A 109.5 . . ? H4B C4 H4A 109.5 . . ? C19 C20 C21 120.4(2) . . ? C19 C20 H20 119.8 . . ? C21 C20 H20 119.8 . . ? C19 C18 C17 120.8(3) . . ? C19 C18 H18 119.6 . . ? C17 C18 H18 119.6 . . ? C1 C5 H5A 109.5 . . ? C1 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? C1 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? H5C C5 H5B 109.5 . . ? C13 C12 C11 120.7(3) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C20 C19 C18 119.0(3) . . ? C20 C19 H19 120.5 . . ? C18 C19 H19 120.5 . . ? C13 C14 C15 121.4(3) . . ? C13 C14 H14 119.3 . . ? C15 C14 H14 119.3 . . ? C14 C13 C12 118.6(3) . . ? C14 C13 H13 120.7 . . ? C12 C13 H13 120.7 . . ? 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 C1 O1 C2 C3 -33.0(2) . . . . ? C1 O1 C2 C6 -159.04(18) . . . . ? C1 O2 C3 C2 -15.3(2) . . . . ? C1 O2 C3 C8 -142.33(19) . . . . ? O1 C2 C3 O2 29.15(19) . . . . ? C6 C2 C3 O2 148.27(16) . . . . ? O1 C2 C3 C8 149.69(16) . . . . ? C6 C2 C3 C8 -91.2(2) . . . . ? O4 C8 C3 O2 -174.46(15) . . . . ? C9 C8 C3 O2 -59.4(2) . . . . ? C16 C8 C3 O2 66.0(2) . . . . ? O4 C8 C3 C2 67.9(2) . . . . ? C9 C8 C3 C2 -177.05(17) . . . . ? C16 C8 C3 C2 -51.6(2) . . . . ? C11 C10 C6 O3 -19.8(3) . . . . ? C15 C10 C6 O3 160.2(2) . . . . ? C11 C10 C6 C7 -136.0(2) . . . . ? C15 C10 C6 C7 43.9(3) . . . . ? C11 C10 C6 C2 101.4(2) . . . . ? C15 C10 C6 C2 -78.6(3) . . . . ? O1 C2 C6 O3 -169.12(16) . . . . ? C3 C2 C6 O3 74.8(2) . . . . ? O1 C2 C6 C10 68.2(2) . . . . ? C3 C2 C6 C10 -47.9(2) . . . . ? O1 C2 C6 C7 -56.3(2) . . . . ? C3 C2 C6 C7 -172.41(19) . . . . ? O4 C8 C16 C17 -15.9(3) . . . . ? C9 C8 C16 C17 -137.0(2) . . . . ? C3 C8 C16 C17 99.2(2) . . . . ? O4 C8 C16 C21 164.9(2) . . . . ? C9 C8 C16 C21 43.8(3) . . . . ? C3 C8 C16 C21 -80.0(3) . . . . ? C21 C16 C17 C18 0.7(4) . . . . ? C8 C16 C17 C18 -178.5(3) . . . . ? C3 O2 C1 O1 -4.4(2) . . . . ? C3 O2 C1 C5 -121.3(2) . . . . ? C3 O2 C1 C4 113.6(2) . . . . ? C2 O1 C1 O2 24.3(3) . . . . ? C2 O1 C1 C5 142.2(2) . . . . ? C2 O1 C1 C4 -93.0(2) . . . . ? C15 C10 C11 C12 -0.2(4) . . . . ? C6 C10 C11 C12 179.8(3) . . . . ? C17 C16 C21 C20 -1.0(4) . . . . ? C8 C16 C21 C20 178.2(2) . . . . ? C11 C10 C15 C14 0.3(4) . . . . ? C6 C10 C15 C14 -179.6(3) . . . . ? C16 C21 C20 C19 0.8(5) . . . . ? C16 C17 C18 C19 -0.2(5) . . . . ? C10 C11 C12 C13 0.3(5) . . . . ? C21 C20 C19 C18 -0.3(5) . . . . ? C17 C18 C19 C20 -0.1(6) . . . . ? C10 C15 C14 C13 -0.6(6) . . . . ? C15 C14 C13 C12 0.7(6) . . . . ? C11 C12 C13 C14 -0.6(6) . . . . ? data_ackcon_m _database_code_depnum_ccdc_archive 'CCDC 771920' #TrackingRef '2aB-acta.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; 'TADDOL FORM B' ; _chemical_name_common "'TADDOL FORM B'" _chemical_melting_point ? _chemical_formula_moiety 'C21 H26 O4' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C21 H26 O4' _chemical_formula_iupac ? _chemical_formula_weight 342.42 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 21' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,1/2+y,-z _cell_length_a 10.882(2) _cell_length_b 7.4911(15) _cell_length_c 12.618(3) _cell_angle_alpha 90 _cell_angle_beta 110.599(3) _cell_angle_gamma 90 _cell_volume 962.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(1) _cell_measurement_reflns_used 3247 _cell_measurement_theta_min 1.7 _cell_measurement_theta_max 24.7 _cell_special_details ; ; _exptl_crystal_description needle _exptl_crystal_colour ' colourless' _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.181 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9685 _exptl_absorpt_correction_T_max 0.9841 _exptl_absorpt_process_details 'Apex2 (Bruker)' _exptl_crystal_density_meas_temp ? #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 293(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Brucker kappa apex2 CCD area detector' _diffrn_measurement_method '\f and \w scans' _chemical_absolute_configuration unk _diffrn_reflns_number 6788 _diffrn_reflns_av_R_equivalents 0.0175 _diffrn_reflns_av_sigmaI/netI 0.0248 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 24.71 _diffrn_reflns_theta_full 24.71 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 3247 # number of observed reflections (> n sig(I)) _reflns_number_gt 2920 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker kappa Apex2' _computing_cell_refinement Apex2 _computing_data_reduction SAINT32 _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'WinGX (Farrugia, 1999)' #=============================================================================== # 8. REFINEMENT DATA _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^)+(0.0385P)^2^+0.0673P] 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 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.4(10) _refine_ls_number_reflns 3247 _refine_ls_number_parameters 232 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0398 _refine_ls_R_factor_gt 0.0342 _refine_ls_wR_factor_ref 0.0815 _refine_ls_wR_factor_gt 0.0784 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.118 _refine_diff_density_min -0.105 _refine_diff_density_rms 0.022 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 0.33858(10) 0.14662(17) 0.84372(9) 0.0477(3) Uani 1 1 d . . . O2 O 0.23924(11) 0.39144(17) 0.88291(9) 0.0499(3) Uani 1 1 d . . . O4 O 0.00502(13) 0.3883(2) 0.59530(9) 0.0575(4) Uani 1 1 d . . . H4 H -0.0490 0.4630 0.5601 0.086 Uiso 1 1 calc R . . O3 O 0.15227(12) 0.14687(19) 0.54130(10) 0.0574(3) Uani 1 1 d . . . H3 H 0.1019 0.2232 0.5488 0.086 Uiso 1 1 calc R . . C6 C 0.27037(16) 0.1461(3) 0.63977(13) 0.0450(4) Uani 1 1 d . . . C2 C 0.22854(16) 0.1813(2) 0.74318(14) 0.0417(4) Uani 1 1 d . . . H2 H 0.1568 0.1000 0.7402 0.050 Uiso 1 1 calc R . . C7 C 0.3257(2) -0.0412(3) 0.64505(19) 0.0633(6) Uani 1 1 d . . . H7B H 0.2629 -0.1263 0.6517 0.095 Uiso 1 1 calc R . . H7C H 0.4053 -0.0510 0.7095 0.095 Uiso 1 1 calc R . . H7A H 0.3440 -0.0647 0.5773 0.095 Uiso 1 1 calc R . . C16 C -0.03771(16) 0.3084(2) 0.76613(14) 0.0448(4) Uani 1 1 d . . . C21 C -0.04613(18) 0.3498(3) 0.87064(16) 0.0551(5) Uani 1 1 d . . . H21 H -0.0053 0.4523 0.9085 0.066 Uiso 1 1 calc R . . C3 C 0.19024(16) 0.3718(2) 0.76235(13) 0.0426(4) Uani 1 1 d . . . H3A H 0.2381 0.4546 0.7308 0.051 Uiso 1 1 calc R . . C15 C 0.49542(18) 0.2923(3) 0.70402(16) 0.0566(5) Uani 1 1 d . . . H15 H 0.5237 0.2085 0.7620 0.068 Uiso 1 1 calc R . . C1 C 0.31991(17) 0.2415(3) 0.93364(14) 0.0481(5) Uani 1 1 d . . . C4 C 0.2485(2) 0.1258(3) 0.99182(17) 0.0671(6) Uani 1 1 d . . . H4C H 0.2310 0.1940 1.0493 0.101 Uiso 1 1 calc R . . H4B H 0.3021 0.0247 1.0258 0.101 Uiso 1 1 calc R . . H4A H 0.1672 0.0852 0.9372 0.101 Uiso 1 1 calc R . . C11 C 0.3291(2) 0.4130(3) 0.54328(16) 0.0571(5) Uani 1 1 d . . . H11 H 0.2440 0.4115 0.4909 0.069 Uiso 1 1 calc R . . C17 C -0.10025(18) 0.1552(3) 0.71244(17) 0.0579(5) Uani 1 1 d . . . H17 H -0.0968 0.1245 0.6421 0.070 Uiso 1 1 calc R . . C8 C 0.04296(18) 0.4225(2) 0.71497(14) 0.0461(4) Uani 1 1 d . . . C12 C 0.4160(2) 0.5417(3) 0.5346(2) 0.0701(6) Uani 1 1 d . . . H12 H 0.3886 0.6267 0.4774 0.084 Uiso 1 1 calc R . . C10 C 0.36648(17) 0.2865(3) 0.62842(14) 0.0439(4) Uani 1 1 d . . . C9 C 0.0288(2) 0.6210(3) 0.73363(17) 0.0640(6) Uani 1 1 d . . . H9A H 0.0727 0.6882 0.6927 0.096 Uiso 1 1 calc R . . H9C H 0.0674 0.6476 0.8129 0.096 Uiso 1 1 calc R . . H9B H -0.0626 0.6523 0.7070 0.096 Uiso 1 1 calc R . . C18 C -0.1678(2) 0.0471(3) 0.7620(2) 0.0740(6) Uani 1 1 d . . . H18 H -0.2089 -0.0557 0.7249 0.089 Uiso 1 1 calc R . . C13 C 0.5423(2) 0.5446(3) 0.6100(2) 0.0707(6) Uani 1 1 d . . . H13 H 0.6009 0.6309 0.6037 0.085 Uiso 1 1 calc R . . C20 C -0.1139(2) 0.2416(4) 0.91909(19) 0.0672(6) Uani 1 1 d . . . H20 H -0.1183 0.2718 0.9892 0.081 Uiso 1 1 calc R . . C14 C 0.5819(2) 0.4202(4) 0.69432(18) 0.0667(6) Uani 1 1 d . . . H14 H 0.6676 0.4218 0.7455 0.080 Uiso 1 1 calc R . . C5 C 0.4518(2) 0.3058(3) 1.0128(2) 0.0799(7) Uani 1 1 d . . . H5A H 0.4953 0.3705 0.9706 0.120 Uiso 1 1 calc R . . H5B H 0.5044 0.2052 1.0491 0.120 Uiso 1 1 calc R . . H5C H 0.4394 0.3827 1.0692 0.120 Uiso 1 1 calc R . . C19 C -0.1748(2) 0.0903(3) 0.8655(2) 0.0735(7) Uani 1 1 d . . . H19 H -0.2204 0.0175 0.8986 0.088 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 0.0466(6) 0.0502(7) 0.0415(6) 0.0040(6) 0.0095(5) 0.0086(6) O2 0.0573(7) 0.0473(7) 0.0372(6) -0.0049(6) 0.0069(5) 0.0045(6) O4 0.0671(9) 0.0654(9) 0.0332(6) 0.0060(6) 0.0092(6) 0.0217(7) O3 0.0563(7) 0.0618(9) 0.0454(7) -0.0158(7) 0.0072(6) -0.0019(7) C6 0.0480(9) 0.0434(10) 0.0393(9) -0.0044(8) 0.0100(8) 0.0033(9) C2 0.0413(9) 0.0388(10) 0.0411(9) 0.0028(7) 0.0098(7) -0.0009(8) C7 0.0738(15) 0.0496(12) 0.0682(13) -0.0062(10) 0.0272(11) 0.0063(10) C16 0.0395(9) 0.0502(11) 0.0397(9) 0.0012(8) 0.0076(7) 0.0113(8) C21 0.0550(11) 0.0613(13) 0.0461(10) -0.0010(9) 0.0143(9) 0.0112(10) C3 0.0493(10) 0.0409(10) 0.0356(9) 0.0012(8) 0.0124(7) -0.0024(8) C15 0.0512(11) 0.0687(13) 0.0500(11) 0.0099(10) 0.0181(9) 0.0057(11) C1 0.0471(10) 0.0498(12) 0.0406(9) 0.0023(8) 0.0068(8) 0.0054(9) C4 0.0752(13) 0.0712(15) 0.0593(12) 0.0167(11) 0.0290(11) 0.0099(12) C11 0.0594(11) 0.0594(13) 0.0495(10) 0.0079(10) 0.0153(9) 0.0070(10) C17 0.0543(11) 0.0620(13) 0.0550(11) -0.0058(11) 0.0161(9) -0.0007(11) C8 0.0521(10) 0.0455(11) 0.0364(9) 0.0015(8) 0.0104(8) 0.0101(8) C12 0.0861(16) 0.0586(14) 0.0697(14) 0.0155(11) 0.0326(12) 0.0041(13) C10 0.0498(10) 0.0456(10) 0.0385(9) -0.0040(8) 0.0183(8) 0.0052(8) C9 0.0788(14) 0.0515(12) 0.0581(12) 0.0047(10) 0.0195(10) 0.0173(11) C18 0.0661(14) 0.0643(15) 0.0882(17) 0.0010(13) 0.0229(12) -0.0079(12) C13 0.0780(15) 0.0692(15) 0.0759(15) -0.0028(13) 0.0409(13) -0.0163(13) C20 0.0675(13) 0.0829(17) 0.0552(12) 0.0148(12) 0.0265(11) 0.0205(13) C14 0.0529(12) 0.0872(17) 0.0615(12) -0.0008(13) 0.0221(10) -0.0101(12) C5 0.0596(13) 0.0821(17) 0.0750(15) -0.0152(13) -0.0052(11) -0.0021(13) C19 0.0644(14) 0.0784(18) 0.0844(17) 0.0241(14) 0.0347(13) 0.0101(13) _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 1.413(2) . ? O1 C2 1.4289(19) . ? O2 C1 1.431(2) . ? O2 C3 1.4316(19) . ? O4 C8 1.441(2) . ? O4 H4 0.8200 . ? O3 C6 1.439(2) . ? O3 H3 0.8200 . ? C6 C7 1.519(3) . ? C6 C10 1.525(3) . ? C6 C2 1.548(2) . ? C2 C3 1.530(2) . ? C2 H2 0.9800 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C7 H7A 0.9600 . ? C16 C17 1.384(3) . ? C16 C21 1.389(2) . ? C16 C8 1.522(2) . ? C21 C20 1.375(3) . ? C21 H21 0.9300 . ? C3 C8 1.548(2) . ? C3 H3A 0.9800 . ? C15 C14 1.378(3) . ? C15 C10 1.392(3) . ? C15 H15 0.9300 . ? C1 C5 1.510(3) . ? C1 C4 1.515(3) . ? C4 H4C 0.9600 . ? C4 H4B 0.9600 . ? C4 H4A 0.9600 . ? C11 C12 1.381(3) . ? C11 C10 1.382(3) . ? C11 H11 0.9300 . ? C17 C18 1.382(3) . ? C17 H17 0.9300 . ? C8 C9 1.521(3) . ? C12 C13 1.369(3) . ? C12 H12 0.9300 . ? C9 H9A 0.9600 . ? C9 H9C 0.9600 . ? C9 H9B 0.9600 . ? C18 C19 1.373(3) . ? C18 H18 0.9300 . ? C13 C14 1.365(3) . ? C13 H13 0.9300 . ? C20 C19 1.367(3) . ? C20 H20 0.9300 . ? C14 H14 0.9300 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C19 H19 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C2 108.01(12) . . ? C1 O2 C3 109.59(13) . . ? C8 O4 H4 109.5 . . ? C6 O3 H3 109.5 . . ? O3 C6 C7 105.16(15) . . ? O3 C6 C10 110.47(14) . . ? C7 C6 C10 111.50(15) . . ? O3 C6 C2 106.79(13) . . ? C7 C6 C2 110.48(15) . . ? C10 C6 C2 112.11(14) . . ? O1 C2 C3 102.65(13) . . ? O1 C2 C6 108.32(13) . . ? C3 C2 C6 117.99(15) . . ? O1 C2 H2 109.2 . . ? C3 C2 H2 109.2 . . ? C6 C2 H2 109.2 . . ? C6 C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C7 H7A 109.5 . . ? H7B C7 H7A 109.5 . . ? H7C C7 H7A 109.5 . . ? C17 C16 C21 117.68(18) . . ? C17 C16 C8 121.06(16) . . ? C21 C16 C8 121.20(17) . . ? C20 C21 C16 121.0(2) . . ? C20 C21 H21 119.5 . . ? C16 C21 H21 119.5 . . ? O2 C3 C2 104.10(13) . . ? O2 C3 C8 109.45(13) . . ? C2 C3 C8 118.09(14) . . ? O2 C3 H3A 108.3 . . ? C2 C3 H3A 108.3 . . ? C8 C3 H3A 108.3 . . ? C14 C15 C10 121.03(19) . . ? C14 C15 H15 119.5 . . ? C10 C15 H15 119.5 . . ? O1 C1 O2 105.94(13) . . ? O1 C1 C5 108.68(16) . . ? O2 C1 C5 109.65(17) . . ? O1 C1 C4 110.14(16) . . ? O2 C1 C4 109.13(15) . . ? C5 C1 C4 113.06(18) . . ? C1 C4 H4C 109.5 . . ? C1 C4 H4B 109.5 . . ? H4C C4 H4B 109.5 . . ? C1 C4 H4A 109.5 . . ? H4C C4 H4A 109.5 . . ? H4B C4 H4A 109.5 . . ? C12 C11 C10 121.2(2) . . ? C12 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C18 C17 C16 120.8(2) . . ? C18 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? O4 C8 C9 109.19(15) . . ? O4 C8 C16 110.43(15) . . ? C9 C8 C16 112.23(16) . . ? O4 C8 C3 103.70(13) . . ? C9 C8 C3 109.12(16) . . ? C16 C8 C3 111.81(13) . . ? C13 C12 C11 120.3(2) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C11 C10 C15 117.45(19) . . ? C11 C10 C6 121.47(17) . . ? C15 C10 C6 121.08(16) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? H9C C9 H9B 109.5 . . ? C19 C18 C17 120.6(2) . . ? C19 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? C14 C13 C12 119.6(2) . . ? C14 C13 H13 120.2 . . ? C12 C13 H13 120.2 . . ? C19 C20 C21 120.8(2) . . ? C19 C20 H20 119.6 . . ? C21 C20 H20 119.6 . . ? C13 C14 C15 120.4(2) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C1 C5 H5A 109.5 . . ? C1 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C1 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C20 C19 C18 119.1(2) . . ? C20 C19 H19 120.4 . . ? C18 C19 H19 120.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 O1 C2 C3 31.84(17) . . . . ? C1 O1 C2 C6 157.37(14) . . . . ? O3 C6 C2 O1 168.67(14) . . . . ? C7 C6 C2 O1 54.83(19) . . . . ? C10 C6 C2 O1 -70.20(17) . . . . ? O3 C6 C2 C3 -75.40(19) . . . . ? C7 C6 C2 C3 170.76(16) . . . . ? C10 C6 C2 C3 45.73(19) . . . . ? C17 C16 C21 C20 0.2(3) . . . . ? C8 C16 C21 C20 -176.84(16) . . . . ? C1 O2 C3 C2 9.24(17) . . . . ? C1 O2 C3 C8 136.37(15) . . . . ? O1 C2 C3 O2 -24.57(16) . . . . ? C6 C2 C3 O2 -143.53(13) . . . . ? O1 C2 C3 C8 -146.13(14) . . . . ? C6 C2 C3 C8 94.91(18) . . . . ? C2 O1 C1 O2 -26.90(17) . . . . ? C2 O1 C1 C5 -144.65(17) . . . . ? C2 O1 C1 C4 90.98(16) . . . . ? C3 O2 C1 O1 10.00(17) . . . . ? C3 O2 C1 C5 127.10(17) . . . . ? C3 O2 C1 C4 -108.56(17) . . . . ? C21 C16 C17 C18 -0.4(3) . . . . ? C8 C16 C17 C18 176.68(18) . . . . ? C17 C16 C8 O4 20.8(2) . . . . ? C21 C16 C8 O4 -162.25(15) . . . . ? C17 C16 C8 C9 142.85(17) . . . . ? C21 C16 C8 C9 -40.2(2) . . . . ? C17 C16 C8 C3 -94.15(19) . . . . ? C21 C16 C8 C3 82.83(19) . . . . ? O2 C3 C8 O4 -177.14(14) . . . . ? C2 C3 C8 O4 -58.36(19) . . . . ? O2 C3 C8 C9 66.58(18) . . . . ? C2 C3 C8 C9 -174.64(16) . . . . ? O2 C3 C8 C16 -58.16(18) . . . . ? C2 C3 C8 C16 60.62(19) . . . . ? C10 C11 C12 C13 0.9(3) . . . . ? C12 C11 C10 C15 -0.9(3) . . . . ? C12 C11 C10 C6 178.86(18) . . . . ? C14 C15 C10 C11 0.4(3) . . . . ? C14 C15 C10 C6 -179.38(18) . . . . ? O3 C6 C10 C11 10.7(2) . . . . ? C7 C6 C10 C11 127.21(19) . . . . ? C2 C6 C10 C11 -108.32(18) . . . . ? O3 C6 C10 C15 -169.61(16) . . . . ? C7 C6 C10 C15 -53.1(2) . . . . ? C2 C6 C10 C15 71.4(2) . . . . ? C16 C17 C18 C19 0.3(3) . . . . ? C11 C12 C13 C14 -0.4(4) . . . . ? C16 C21 C20 C19 0.0(3) . . . . ? C12 C13 C14 C15 -0.1(4) . . . . ? C10 C15 C14 C13 0.1(3) . . . . ? C21 C20 C19 C18 -0.1(3) . . . . ? C17 C18 C19 C20 -0.1(3) . . . . ? #===END