# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2002 data_kdk01 _database_code_CSD 183073 _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'Ylihonko, Kristiina' 'Blanco, Gloria' 'Hakala, Juha' 'Klika, Karel D.' 'Kunnari, Tero' 'Mantsala, Pekka' 'Mendez, Carmen' 'Salas, Jose' _publ_contact_author_name 'Dr Kristiina Ylihonko' _publ_contact_author_address ; Galilaeus Oy P.O. Box 113 Kaarina FIN 20781 FINLAND ; _publ_contact_author_email 'KRISTIINA.YLIHONKO@GALILAEUS.FI' _publ_section_title ; Hybrid compounds generated by the introduction of a nogalamycin-producing plasmid into Streptomyces argillaceus ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H18 O8' _chemical_formula_weight 398.35 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.1675(2) _cell_length_b 10.5383(6) _cell_length_c 16.2748(9) _cell_angle_alpha 90.00 _cell_angle_beta 98.367(2) _cell_angle_gamma 90.00 _cell_volume 876.84(8) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2753 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 25.03 _exptl_crystal_description plate _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.02 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.509 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 0.117 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9884 _exptl_absorpt_correction_T_max 0.9884 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_ambient_temperature 173(2) _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_radiation_probe x-ray _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enraf Nonius FR590' _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_standards_decay_% ? _diffrn_reflns_number 5231 _diffrn_reflns_av_R_equivalents 0.0875 _diffrn_reflns_av_sigmaI/netI 0.1363 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.18 _diffrn_reflns_theta_max 25.11 _reflns_number_total 3055 _reflns_number_gt 1873 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0000P)^2^+1.0352P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.7(2.2) _refine_ls_number_reflns 3055 _refine_ls_number_parameters 273 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1416 _refine_ls_R_factor_gt 0.0711 _refine_ls_wR_factor_ref 0.1324 _refine_ls_wR_factor_gt 0.1098 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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 0.2080(8) 0.7439(4) 0.4864(3) 0.0366(11) Uani 1 1 d . . . O1' O -0.3955(8) 0.5185(4) 0.5557(3) 0.0348(11) Uani 1 1 d . . . H1' H -0.457(15) 0.465(7) 0.493(6) 0.08(3) Uiso 1 1 d . . . O3 O -0.4723(8) 0.4494(4) 0.4109(3) 0.0341(11) Uani 1 1 d . . . O4 O -0.2311(7) 0.4047(4) 0.2746(2) 0.0343(10) Uani 1 1 d . . . O10 O -0.9027(10) 1.0770(4) 0.1403(3) 0.0463(13) Uani 1 1 d . . . H10 H -0.783(14) 1.095(7) 0.185(5) 0.07(3) Uiso 1 1 d . . . O11 O -0.5135(9) 1.0053(4) 0.2502(3) 0.0330(11) Uani 1 1 d . . . H11 H -0.415(15) 0.993(8) 0.301(5) 0.08(3) Uiso 1 1 d . . . O12 O -0.1875(7) 0.9071(4) 0.3613(2) 0.0292(10) Uani 1 1 d . . . O12A O 0.3044(7) 0.7651(4) 0.3352(3) 0.0277(10) Uiso 1 1 d . . . H12A H 0.323(11) 0.829(6) 0.370(4) 0.039(18) Uiso 1 1 d . . . C1 C 0.0431(11) 0.6913(6) 0.4365(4) 0.0242(14) Uani 1 1 d . . . C1' C -0.2240(11) 0.5975(6) 0.5400(4) 0.0256(14) Uani 1 1 d . . . C2 C -0.1574(10) 0.6065(5) 0.4576(3) 0.0201(13) Uani 1 1 d . . . C3 C -0.2932(10) 0.5287(5) 0.3964(4) 0.0237(14) Uani 1 1 d . . . C4 C -0.2456(11) 0.5307(5) 0.3060(4) 0.0233(13) Uani 1 1 d . . . H4 H -0.3955 0.5753 0.2721 0.028 Uiso 1 1 calc R . . C4A C 0.0076(10) 0.5965(6) 0.2922(4) 0.0232(14) Uani 1 1 d . . . H4A H 0.1565 0.5373 0.3100 0.028 Uiso 1 1 calc R . . C5 C 0.0063(11) 0.6291(6) 0.2003(4) 0.0264(15) Uani 1 1 d . . . H5A H 0.1774 0.6661 0.1928 0.032 Uiso 1 1 calc R . . H5B H -0.0188 0.5505 0.1668 0.032 Uiso 1 1 calc R . . C5A C -0.2075(10) 0.7216(5) 0.1701(3) 0.0232(14) Uani 1 1 d . . . C6 C -0.3484(11) 0.7140(6) 0.0930(4) 0.0324(17) Uani 1 1 d . . . H6 H -0.3075 0.6495 0.0562 0.039 Uiso 1 1 calc R . . C6A C -0.5555(11) 0.7999(6) 0.0660(4) 0.0254(15) Uani 1 1 d . . . C7 C -0.7097(12) 0.7859(6) -0.0129(4) 0.0377(17) Uani 1 1 d . . . H7 H -0.6681 0.7216 -0.0497 0.045 Uiso 1 1 calc R . . C8 C -0.9177(13) 0.8644(7) -0.0362(4) 0.0405(18) Uani 1 1 d . . . H8 H -1.0220 0.8525 -0.0887 0.049 Uiso 1 1 calc R . . C9 C -0.9795(13) 0.9614(7) 0.0156(4) 0.0397(18) Uani 1 1 d . . . H9 H -1.1239 1.0156 -0.0020 0.048 Uiso 1 1 calc R . . C10 C -0.8314(11) 0.9792(6) 0.0927(4) 0.0308(16) Uani 1 1 d . . . C10A C -0.6138(10) 0.9001(6) 0.1186(4) 0.0242(14) Uani 1 1 d . . . C11 C -0.4582(10) 0.9095(6) 0.1997(3) 0.0260(14) Uani 1 1 d . . . C11A C -0.2632(11) 0.8204(5) 0.2269(4) 0.0224(13) Uani 1 1 d . . . C12 C -0.1433(10) 0.8205(5) 0.3121(4) 0.0215(13) Uani 1 1 d . . . C12A C 0.0517(9) 0.7164(5) 0.3434(3) 0.0191(14) Uani 1 1 d . . . C13 C -0.1052(14) 0.6817(7) 0.6087(4) 0.0449(19) Uani 1 1 d . . . H13A H -0.1666 0.7689 0.5976 0.067 Uiso 1 1 calc R . . H13B H 0.0858 0.6792 0.6125 0.067 Uiso 1 1 calc R . . H13C H -0.1563 0.6525 0.6612 0.067 Uiso 1 1 calc R . . C14 C -0.4658(12) 0.3557(7) 0.2290(4) 0.0437(19) Uani 1 1 d . . . H14A H -0.5984 0.3467 0.2659 0.065 Uiso 1 1 calc R . . H14B H -0.4307 0.2726 0.2059 0.065 Uiso 1 1 calc R . . H14C H -0.5297 0.4141 0.1837 0.065 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 0.033(2) 0.046(3) 0.029(3) -0.005(2) 0.001(2) -0.015(2) O1' 0.030(2) 0.047(3) 0.029(3) 0.009(2) 0.011(2) -0.006(2) O3 0.031(2) 0.040(3) 0.030(3) 0.009(2) 0.000(2) -0.016(2) O4 0.037(2) 0.025(3) 0.038(3) -0.008(2) -0.002(2) 0.000(2) O10 0.051(3) 0.039(3) 0.046(3) -0.003(3) -0.004(3) 0.011(3) O11 0.049(3) 0.020(3) 0.029(3) -0.006(2) 0.003(2) 0.008(2) O12 0.028(2) 0.031(3) 0.029(2) -0.006(2) 0.0037(19) 0.004(2) C1 0.024(3) 0.020(3) 0.029(3) 0.002(3) 0.005(3) 0.004(3) C1' 0.024(3) 0.026(4) 0.026(4) 0.001(3) 0.005(3) 0.003(3) C2 0.015(3) 0.023(3) 0.022(3) 0.002(3) 0.002(3) -0.001(3) C3 0.016(3) 0.021(4) 0.035(4) 0.011(3) 0.006(3) 0.006(3) C4 0.022(3) 0.018(3) 0.029(3) -0.001(3) 0.000(3) -0.004(3) C4A 0.020(3) 0.020(4) 0.030(4) 0.004(3) 0.004(3) 0.006(3) C5 0.027(3) 0.027(4) 0.024(3) -0.001(3) 0.002(3) 0.003(3) C5A 0.025(3) 0.022(4) 0.024(3) 0.004(3) 0.009(3) -0.006(3) C6 0.032(4) 0.045(5) 0.021(4) 0.002(3) 0.009(3) 0.000(3) C6A 0.027(3) 0.026(4) 0.022(3) 0.000(3) 0.001(3) -0.002(3) C7 0.041(4) 0.047(5) 0.023(4) 0.003(3) -0.003(3) -0.003(4) C8 0.049(4) 0.047(5) 0.024(4) 0.012(3) -0.003(3) -0.009(4) C9 0.038(4) 0.042(5) 0.038(4) 0.013(3) 0.001(4) 0.002(3) C10 0.031(3) 0.032(4) 0.029(4) 0.009(3) 0.003(3) 0.001(3) C10A 0.021(3) 0.023(4) 0.027(3) 0.011(3) 0.000(3) -0.001(3) C11 0.029(3) 0.025(4) 0.023(3) 0.009(3) 0.002(3) -0.009(3) C11A 0.028(3) 0.013(3) 0.026(3) 0.001(3) 0.001(3) -0.005(3) C12 0.023(3) 0.021(3) 0.022(3) -0.004(3) 0.007(3) -0.011(3) C12A 0.007(3) 0.025(4) 0.025(3) 0.001(3) 0.003(2) 0.000(2) C13 0.064(5) 0.047(5) 0.025(4) -0.003(4) 0.011(4) -0.005(4) C14 0.041(4) 0.044(5) 0.045(4) -0.008(3) 0.003(3) -0.017(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.221(7) . y O1' C1' 1.269(6) . y O1' H1' 1.17(9) . y O3 C3 1.294(6) . y O3 H1' 1.33(9) . y O4 C14 1.424(7) . ? O4 C4 1.428(7) . y O10 C10 1.371(8) . ? O10 H10 0.90(8) . ? O11 C11 1.358(7) . ? O11 H11 0.91(8) . ? O12 C12 1.258(6) . ? O12A C12A 1.427(6) . ? O12A H12A 0.88(6) . ? C1 C2 1.447(7) . y C1 C12A 1.547(7) . ? C1' C2 1.435(8) . y C1' C13 1.487(8) . ? C2 C3 1.398(8) . y C3 C4 1.527(8) . y C4 C4A 1.526(7) . ? C4 H4 1.0000 . ? C4A C12A 1.512(8) . ? C4A C5 1.534(8) . ? C4A H4A 1.0000 . ? C5 C5A 1.501(8) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C5A C6 1.358(8) . ? C5A C11A 1.448(8) . ? C6 C6A 1.422(8) . ? C6 H6 0.9500 . ? C6A C7 1.417(9) . ? C6A C10A 1.419(8) . ? C7 C8 1.365(9) . ? C7 H7 0.9500 . ? C8 C9 1.392(9) . ? C8 H8 0.9500 . ? C9 C10 1.384(9) . ? C9 H9 0.9500 . ? C10 C10A 1.414(8) . ? C10A C11 1.445(8) . ? C11 C11A 1.401(8) . ? C11A C12 1.434(8) . ? C12 C12A 1.526(7) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1' O1' H1' 105(4) . . ? C3 O3 H1' 100(3) . . ? C14 O4 C4 116.0(5) . . ? C10 O10 H10 114(5) . . ? C11 O11 H11 108(5) . . ? C12A O12A H12A 103(4) . . ? O1 C1 C2 125.3(5) . . ? O1 C1 C12A 117.2(5) . . ? C2 C1 C12A 117.5(5) . . ? O1' C1' C2 120.0(5) . . ? O1' C1' C13 117.7(5) . . ? C2 C1' C13 122.3(5) . . ? C3 C2 C1' 117.7(5) . . ? C3 C2 C1 119.7(5) . . ? C1' C2 C1 122.7(5) . . ? O3 C3 C2 123.1(5) . . ? O3 C3 C4 113.9(5) . . ? C2 C3 C4 123.0(5) . . ? O4 C4 C4A 106.2(4) . . ? O4 C4 C3 110.9(5) . . ? C4A C4 C3 114.1(5) . . ? O4 C4 H4 108.5 . . ? C4A C4 H4 108.5 . . ? C3 C4 H4 108.5 . . ? C12A C4A C4 111.3(4) . . ? C12A C4A C5 109.2(5) . . ? C4 C4A C5 111.3(5) . . ? C12A C4A H4A 108.3 . . ? C4 C4A H4A 108.3 . . ? C5 C4A H4A 108.3 . . ? C5A C5 C4A 111.3(4) . . ? C5A C5 H5A 109.4 . . ? C4A C5 H5A 109.4 . . ? C5A C5 H5B 109.4 . . ? C4A C5 H5B 109.4 . . ? H5A C5 H5B 108.0 . . ? C6 C5A C11A 120.1(5) . . ? C6 C5A C5 122.3(5) . . ? C11A C5A C5 117.6(5) . . ? C5A C6 C6A 121.8(5) . . ? C5A C6 H6 119.1 . . ? C6A C6 H6 119.1 . . ? C7 C6A C10A 118.9(6) . . ? C7 C6A C6 120.8(6) . . ? C10A C6A C6 120.2(5) . . ? C8 C7 C6A 120.3(6) . . ? C8 C7 H7 119.8 . . ? C6A C7 H7 119.8 . . ? C7 C8 C9 121.1(7) . . ? C7 C8 H8 119.4 . . ? C9 C8 H8 119.4 . . ? C10 C9 C8 120.2(6) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? O10 C10 C9 117.1(6) . . ? O10 C10 C10A 122.8(5) . . ? C9 C10 C10A 120.1(6) . . ? C10 C10A C6A 119.2(5) . . ? C10 C10A C11 123.0(5) . . ? C6A C10A C11 117.6(5) . . ? O11 C11 C11A 120.8(5) . . ? O11 C11 C10A 117.7(5) . . ? C11A C11 C10A 121.4(6) . . ? C11 C11A C12 119.6(5) . . ? C11 C11A C5A 118.8(5) . . ? C12 C11A C5A 121.2(5) . . ? O12 C12 C11A 121.6(5) . . ? O12 C12 C12A 118.8(5) . . ? C11A C12 C12A 119.6(5) . . ? O12A C12A C4A 108.4(4) . . ? O12A C12A C12 106.2(4) . . ? C4A C12A C12 112.2(5) . . ? O12A C12A C1 108.1(4) . . ? C4A C12A C1 111.9(5) . . ? C12 C12A C1 109.8(4) . . ? C1' C13 H13A 109.5 . . ? C1' C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C1' C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O4 C14 H14A 109.5 . . ? O4 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O4 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 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 O1' C1' C2 C3 2.0(8) . . . . ? C13 C1' C2 C3 -175.8(6) . . . . ? O1' C1' C2 C1 -177.6(5) . . . . ? C13 C1' C2 C1 4.6(9) . . . . ? O1 C1 C2 C3 -164.5(6) . . . . ? C12A C1 C2 C3 14.8(7) . . . . ? O1 C1 C2 C1' 15.1(9) . . . . ? C12A C1 C2 C1' -165.6(5) . . . . ? C1' C2 C3 O3 -0.6(8) . . . . ? C1 C2 C3 O3 179.0(5) . . . . ? C1' C2 C3 C4 178.7(5) . . . . ? C1 C2 C3 C4 -1.6(8) . . . . ? C14 O4 C4 C4A -138.8(5) . . . . ? C14 O4 C4 C3 96.7(6) . . . . ? O3 C3 C4 O4 -45.1(6) . . . . ? C2 C3 C4 O4 135.5(5) . . . . ? O3 C3 C4 C4A -165.0(5) . . . . ? C2 C3 C4 C4A 15.6(8) . . . . ? O4 C4 C4A C12A -164.1(4) . . . . ? C3 C4 C4A C12A -41.7(6) . . . . ? O4 C4 C4A C5 73.8(6) . . . . ? C3 C4 C4A C5 -163.7(5) . . . . ? C12A C4A C5 C5A -60.3(6) . . . . ? C4 C4A C5 C5A 63.0(6) . . . . ? C4A C5 C5A C6 -141.8(6) . . . . ? C4A C5 C5A C11A 37.4(7) . . . . ? C11A C5A C6 C6A -1.1(8) . . . . ? C5 C5A C6 C6A 178.1(5) . . . . ? C5A C6 C6A C7 -176.4(6) . . . . ? C5A C6 C6A C10A 2.5(8) . . . . ? C10A C6A C7 C8 -2.8(9) . . . . ? C6 C6A C7 C8 176.1(6) . . . . ? C6A C7 C8 C9 1.6(10) . . . . ? C7 C8 C9 C10 -0.7(10) . . . . ? C8 C9 C10 O10 179.7(6) . . . . ? C8 C9 C10 C10A 1.0(9) . . . . ? O10 C10 C10A C6A 179.2(5) . . . . ? C9 C10 C10A C6A -2.3(8) . . . . ? O10 C10 C10A C11 4.4(9) . . . . ? C9 C10 C10A C11 -177.0(6) . . . . ? C7 C6A C10A C10 3.1(8) . . . . ? C6 C6A C10A C10 -175.8(5) . . . . ? C7 C6A C10A C11 178.1(5) . . . . ? C6 C6A C10A C11 -0.8(8) . . . . ? C10 C10A C11 O11 -5.1(8) . . . . ? C6A C10A C11 O11 180.0(5) . . . . ? C10 C10A C11 C11A 172.5(5) . . . . ? C6A C10A C11 C11A -2.4(8) . . . . ? O11 C11 C11A C12 7.9(8) . . . . ? C10A C11 C11A C12 -169.7(5) . . . . ? O11 C11 C11A C5A -178.7(5) . . . . ? C10A C11 C11A C5A 3.8(8) . . . . ? C6 C5A C11A C11 -2.0(8) . . . . ? C5 C5A C11A C11 178.7(5) . . . . ? C6 C5A C11A C12 171.3(5) . . . . ? C5 C5A C11A C12 -8.0(7) . . . . ? C11 C11A C12 O12 -7.9(8) . . . . ? C5A C11A C12 O12 178.8(5) . . . . ? C11 C11A C12 C12A 174.7(5) . . . . ? C5A C11A C12 C12A 1.4(7) . . . . ? C4 C4A C12A O12A 173.4(4) . . . . ? C5 C4A C12A O12A -63.4(5) . . . . ? C4 C4A C12A C12 -69.6(6) . . . . ? C5 C4A C12A C12 53.6(5) . . . . ? C4 C4A C12A C1 54.3(6) . . . . ? C5 C4A C12A C1 177.5(4) . . . . ? O12 C12 C12A O12A -84.4(6) . . . . ? C11A C12 C12A O12A 93.1(5) . . . . ? O12 C12 C12A C4A 157.3(4) . . . . ? C11A C12 C12A C4A -25.2(6) . . . . ? O12 C12 C12A C1 32.2(7) . . . . ? C11A C12 C12A C1 -150.3(5) . . . . ? O1 C1 C12A O12A 18.3(7) . . . . ? C2 C1 C12A O12A -161.0(5) . . . . ? O1 C1 C12A C4A 137.6(5) . . . . ? C2 C1 C12A C4A -41.7(6) . . . . ? O1 C1 C12A C12 -97.1(6) . . . . ? C2 C1 C12A C12 83.5(6) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.11 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.254 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.062