# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2001 data_29d _database_code_CSD 158875 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'S Al-Busafi' 'J.R.Doncaster' 'M.G.B.Drew' 'R.C.Whitehead' 'Regan, A.' _publ_contact_author_name 'Dr Roger C Whitehead' _publ_contact_author_address ; Department of Chemistry University of Manchester Oxford Road Manchester M13 9PL UNITED KINGDOM ; _publ_contact_author_email 'ROGER.WHITEHEAD@MAN.AC.UK' _publ_section_title ; Exploitation of Chemical Predisposition in Synthesis: An approach to the Manzamenones ; _publ_section_references ; Kabsch, W. (1988), J.Appl.Cryst 21 916-932. Sheldrick, G.M. (1990) SHELX86, Acta Cryst. A46 467-480. Sheldrick, G.M. (1993) SHELXL program for crystallography refinement. University of Gottingen, Germany. Spek, A.L., (1994) PLATON-94 program, Utrecht University, The Netherlands ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H38 O7' _chemical_formula_weight 462.56 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 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 12.691(14) _cell_length_b 17.33(2) _cell_length_c 12.358(14) _cell_angle_alpha 90.00 _cell_angle_beta 93.440(10) _cell_angle_gamma 90.00 _cell_volume 2713(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9632 _cell_measurement_theta_min 1.99 _cell_measurement_theta_max 26.09 _exptl_crystal_description parallelopiped _exptl_crystal_colour white _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.133 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 'Marresearch Image Plate' _diffrn_measurement_method '95 frames at 2^o intervals, counting time 2 min.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9632 _diffrn_reflns_av_R_equivalents 0.0664 _diffrn_reflns_av_sigmaI/netI 0.0921 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 26.09 _reflns_number_total 5307 _reflns_number_gt 2079 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XDS (Kabsch, 1991)' _computing_cell_refinement XDS _computing_data_reduction XDS _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'PLATON(Spek,1994)' _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 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 0.001(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 5307 _refine_ls_number_parameters 284 _refine_ls_number_restraints 17 _refine_ls_R_factor_all 0.2319 _refine_ls_R_factor_gt 0.1132 _refine_ls_wR_factor_ref 0.3825 _refine_ls_wR_factor_gt 0.3133 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.123 _refine_ls_shift/su_max 0.020 _refine_ls_shift/su_mean 0.003 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4926(4) 0.3576(3) 0.4890(4) 0.0650(14) Uani 1 d . . . H1 H 0.5046 0.4035 0.5345 0.078 Uiso 1 calc R . . C2 C 0.4127(4) 0.3074(3) 0.5400(4) 0.0674(14) Uani 1 d . . . C3 C 0.4075(4) 0.2326(3) 0.5164(4) 0.0719(15) Uani 1 d . . . H3 H 0.3567 0.2030 0.5483 0.086 Uiso 1 calc R . . C4 C 0.4795(4) 0.1928(3) 0.4406(4) 0.0650(14) Uani 1 d . . . H4 H 0.4450 0.1961 0.3677 0.078 Uiso 1 calc R . . C5 C 0.5869(4) 0.2324(3) 0.4361(4) 0.0632(14) Uani 1 d . . . H5 H 0.6377 0.1998 0.4778 0.076 Uiso 1 calc R . . C6 C 0.6272(5) 0.2392(3) 0.3225(4) 0.0711(15) Uani 1 d . . . C7 C 0.6872(5) 0.3119(3) 0.3196(4) 0.0731(15) Uani 1 d . . . C8 C 0.6748(4) 0.3528(3) 0.4113(4) 0.0689(14) Uani 1 d . . . C9 C 0.5989(4) 0.3138(3) 0.4838(4) 0.0634(14) Uani 1 d . . . H9 H 0.6322 0.3101 0.5572 0.076 Uiso 1 calc R . . C11 C 0.4554(5) 0.3838(3) 0.3755(5) 0.0721(15) Uani 1 d . . . O12 O 0.4208(4) 0.3427(2) 0.3050(4) 0.1050(16) Uani 1 d . . . O13 O 0.4712(3) 0.45883(18) 0.3614(3) 0.0780(12) Uani 1 d . . . C14 C 0.4525(6) 0.4886(3) 0.2523(5) 0.101(2) Uani 1 d . . . H14A H 0.3881 0.4672 0.2203 0.121 Uiso 1 calc R . . H14B H 0.5102 0.4744 0.2096 0.121 Uiso 1 calc R . . H14C H 0.4467 0.5438 0.2547 0.121 Uiso 1 calc R . . C21 C 0.3392(5) 0.3484(3) 0.6144(5) 0.0871(18) Uani 1 d . . . H21A H 0.3822 0.3726 0.6725 0.105 Uiso 1 calc R . . H21B H 0.3032 0.3893 0.5734 0.105 Uiso 1 calc R . . C22 C 0.2571(5) 0.2993(4) 0.6647(5) 0.0927(19) Uani 1 d . . . H22A H 0.2918 0.2579 0.7057 0.111 Uiso 1 calc R . . H22B H 0.2116 0.2762 0.6076 0.111 Uiso 1 calc R . . C23 C 0.1894(6) 0.3463(5) 0.7399(7) 0.128(3) Uani 1 d . . . H23A H 0.1495 0.3849 0.6980 0.153 Uiso 1 calc R . . H23B H 0.2348 0.3727 0.7939 0.153 Uiso 1 calc R . . C24 C 0.1112(9) 0.2916(7) 0.7979(10) 0.198(6) Uani 1 d . . . H24A H 0.0583 0.2735 0.7439 0.237 Uiso 1 calc R . . H24B H 0.1506 0.2468 0.8247 0.237 Uiso 1 calc R . . C25 C 0.0596(13) 0.3229(10) 0.8834(12) 0.255(8) Uani 1 d . . . H25A H 0.0213 0.3689 0.8592 0.306 Uiso 1 calc R . . H25B H 0.1107 0.3376 0.9412 0.306 Uiso 1 calc R . . C26 C -0.0191(15) 0.2625(13) 0.9265(15) 0.331(12) Uani 1 d . . . H26A H -0.0246 0.2699 1.0029 0.398 Uiso 1 calc R . . H26B H 0.0063 0.2114 0.9134 0.398 Uiso 1 calc R . . H26C H -0.0873 0.2692 0.8897 0.398 Uiso 1 calc R . . C41 C 0.4906(5) 0.1087(3) 0.4674(4) 0.0646(14) Uani 1 d . . . O42 O 0.5722(3) 0.07632(19) 0.4923(3) 0.0828(12) Uani 1 d . . . O43 O 0.3994(3) 0.0721(2) 0.4587(4) 0.0883(13) Uani 1 d . . . H43 H 0.4071 0.0281 0.4824 0.106 Uiso 1 calc R . . O61 O 0.6106(4) 0.1915(2) 0.2517(3) 0.0965(14) Uani 1 d . . . C71 C 0.7482(5) 0.3329(4) 0.2252(5) 0.0879(18) Uani 1 d . . . O72 O 0.7819(5) 0.2855(3) 0.1639(4) 0.1266(19) Uani 1 d . . . O73 O 0.7572(4) 0.4075(3) 0.2102(4) 0.1069(15) Uani 1 d . . . C74 C 0.8168(7) 0.4298(5) 0.1196(7) 0.134(3) Uani 1 d . . . H74A H 0.7728 0.4262 0.0539 0.161 Uiso 1 calc R . . H74B H 0.8764 0.3960 0.1151 0.161 Uiso 1 calc R . . H74C H 0.8412 0.4819 0.1294 0.161 Uiso 1 calc R . . C81 C 0.7267(5) 0.4279(3) 0.4477(5) 0.0892(18) Uani 1 d D . . H81A H 0.6753 0.4611 0.4794 0.107 Uiso 1 calc R . . H81B H 0.7533 0.4544 0.3857 0.107 Uiso 1 calc R . . C82 C 0.8209(10) 0.4104(7) 0.5341(10) 0.207(5) Uiso 1 d D . . H82A H 0.8868 0.4003 0.5009 0.248 Uiso 1 calc R A 1 H82B H 0.8050 0.3686 0.5827 0.248 Uiso 1 calc R A 1 C83A C 0.8195(17) 0.4937(10) 0.5924(15) 0.172(6) Uiso 0.50 d PD B 1 H83A H 0.8380 0.5349 0.5438 0.206 Uiso 0.50 calc PR B 1 H83B H 0.7515 0.5047 0.6209 0.206 Uiso 0.50 calc PR B 1 C84A C 0.904(2) 0.481(2) 0.681(2) 0.42(3) Uiso 0.50 d PD B 1 H84A H 0.9408 0.4328 0.6722 0.501 Uiso 0.50 calc PR B 1 H84B H 0.9541 0.5232 0.6858 0.501 Uiso 0.50 calc PR B 1 C85A C 0.839(3) 0.4790(14) 0.7762(19) 0.33(2) Uiso 0.50 d PD B 1 H85A H 0.8631 0.4386 0.8262 0.397 Uiso 0.50 calc PR B 1 H85B H 0.7655 0.4709 0.7548 0.397 Uiso 0.50 calc PR B 1 C86A C 0.8580(12) 0.5603(7) 0.8273(11) 0.274(8) Uiso 0.50 d PD B 1 H86A H 0.9050 0.5892 0.7848 0.329 Uiso 0.50 calc PR B 1 H86B H 0.8885 0.5549 0.8999 0.329 Uiso 0.50 calc PR B 1 H86C H 0.7918 0.5870 0.8289 0.329 Uiso 0.50 calc PR B 1 C83B C 0.8757(12) 0.4839(7) 0.5662(11) 0.172(6) Uiso 0.50 d PRD B 2 H83C H 0.9516 0.4784 0.5637 0.206 Uiso 0.50 calc PR B 2 H83D H 0.8522 0.5257 0.5186 0.206 Uiso 0.50 calc PR B 2 C84B C 0.8496(12) 0.4968(7) 0.6655(11) 0.204(11) Uiso 0.50 d PRD B 2 H84C H 0.8462 0.4468 0.7004 0.244 Uiso 0.50 calc PR B 2 H84D H 0.7780 0.5167 0.6600 0.244 Uiso 0.50 calc PR B 2 C85B C 0.9050(10) 0.5431(7) 0.7353(13) 0.32(2) Uiso 0.50 d PRD B 2 H85C H 0.9196 0.5909 0.6983 0.385 Uiso 0.50 calc PR B 2 H85D H 0.9722 0.5186 0.7546 0.385 Uiso 0.50 calc PR B 2 C86B C 0.8580(12) 0.5603(7) 0.8273(11) 0.274(8) Uiso 0.50 d PRD B 2 H86D H 0.7858 0.5746 0.8101 0.329 Uiso 0.50 calc PR B 2 H86E H 0.8945 0.6025 0.8633 0.329 Uiso 0.50 calc PR B 2 H86F H 0.8602 0.5161 0.8742 0.329 Uiso 0.50 calc PR B 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 C1 0.101(4) 0.041(2) 0.053(3) -0.002(2) 0.011(3) -0.006(3) C2 0.089(4) 0.044(3) 0.070(3) -0.002(2) 0.010(3) 0.000(3) C3 0.096(4) 0.045(3) 0.076(4) 0.001(3) 0.016(3) -0.005(3) C4 0.094(4) 0.042(2) 0.059(3) 0.001(2) 0.005(3) -0.003(3) C5 0.089(4) 0.045(2) 0.056(3) 0.002(2) 0.008(3) 0.001(3) C6 0.100(4) 0.052(3) 0.062(3) -0.006(3) 0.012(3) -0.002(3) C7 0.105(4) 0.054(3) 0.062(3) 0.001(3) 0.015(3) -0.005(3) C8 0.087(4) 0.057(3) 0.061(3) 0.002(3) 0.002(3) -0.003(3) C9 0.091(4) 0.045(2) 0.053(3) 0.004(2) 0.002(3) -0.007(3) C11 0.103(4) 0.042(3) 0.071(4) 0.002(3) 0.002(3) 0.002(3) O12 0.172(4) 0.055(2) 0.083(3) 0.002(2) -0.037(3) -0.018(3) O13 0.121(3) 0.0427(19) 0.070(2) 0.0077(17) 0.007(2) -0.0053(19) C14 0.160(6) 0.073(4) 0.069(4) 0.024(3) 0.000(4) -0.007(4) C21 0.106(5) 0.059(3) 0.098(5) -0.001(3) 0.024(4) 0.009(3) C22 0.100(4) 0.083(4) 0.098(5) 0.001(4) 0.028(4) 0.011(4) C23 0.123(6) 0.131(7) 0.132(7) -0.028(5) 0.040(5) 0.016(5) C24 0.177(9) 0.202(11) 0.229(12) -0.087(9) 0.146(10) -0.034(8) C25 0.255(17) 0.279(18) 0.242(17) -0.044(14) 0.100(14) -0.058(14) C26 0.30(2) 0.42(3) 0.29(2) -0.02(2) 0.175(18) -0.151(19) C41 0.087(4) 0.037(2) 0.070(3) -0.006(2) 0.007(3) -0.006(3) O42 0.099(3) 0.0380(18) 0.111(3) 0.0103(19) 0.004(2) 0.002(2) O43 0.104(3) 0.0390(18) 0.121(4) 0.009(2) 0.003(2) 0.001(2) O61 0.147(4) 0.071(2) 0.074(3) -0.023(2) 0.024(2) -0.019(3) C71 0.112(5) 0.071(4) 0.082(4) 0.000(3) 0.019(4) -0.001(4) O72 0.178(5) 0.099(4) 0.110(4) -0.011(3) 0.064(4) -0.022(3) O73 0.146(4) 0.081(3) 0.098(3) 0.010(2) 0.043(3) -0.018(3) C74 0.152(7) 0.137(7) 0.117(6) 0.035(5) 0.038(5) -0.034(6) C81 0.125(5) 0.062(3) 0.080(4) -0.003(3) 0.008(4) -0.010(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 C1 C2 1.502(7) . ? C1 C11 1.522(7) . ? C1 C9 1.553(7) . ? C2 C3 1.330(7) . ? C2 C21 1.524(8) . ? C3 C4 1.513(7) . ? C4 C41 1.499(7) . ? C4 C5 1.531(7) . ? C5 C6 1.527(7) . ? C5 C9 1.533(6) . ? C6 O61 1.214(6) . ? C6 C7 1.473(7) . ? C7 C8 1.355(7) . ? C7 C71 1.483(8) . ? C8 C81 1.515(7) . ? C8 C9 1.514(7) . ? C11 O12 1.189(6) . ? C11 O13 1.328(6) . ? O13 C14 1.450(7) . ? C21 C22 1.509(8) . ? C22 C23 1.536(9) . ? C23 C24 1.576(12) . ? C24 C25 1.387(14) . ? C25 C26 1.562(17) . ? C41 O42 1.201(6) . ? C41 O43 1.319(6) . ? C71 O72 1.212(7) . ? C71 O73 1.313(7) . ? O73 C74 1.441(8) . ? C81 C82 1.584(11) . ? C82 C83B 1.493(14) . ? C82 C83A 1.614(15) . ? C83A C84A 1.50(2) . ? C84A C85A 1.47(2) . ? C85A C86A 1.56(2) . ? C83B C84B 1.309(3) . ? C84B C85B 1.345(2) . ? C85B C86B 1.3495 . ? 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 C2 C1 C11 112.3(5) . . ? C2 C1 C9 110.1(4) . . ? C11 C1 C9 109.2(4) . . ? C3 C2 C1 119.9(5) . . ? C3 C2 C21 124.2(5) . . ? C1 C2 C21 115.8(4) . . ? C2 C3 C4 123.8(5) . . ? C41 C4 C3 111.0(4) . . ? C41 C4 C5 111.8(4) . . ? C3 C4 C5 113.0(4) . . ? C6 C5 C9 104.5(4) . . ? C6 C5 C4 114.6(4) . . ? C9 C5 C4 117.8(4) . . ? O61 C6 C7 129.2(5) . . ? O61 C6 C5 123.8(5) . . ? C7 C6 C5 107.0(4) . . ? C8 C7 C6 109.9(5) . . ? C8 C7 C71 128.5(5) . . ? C6 C7 C71 121.6(5) . . ? C7 C8 C81 128.9(5) . . ? C7 C8 C9 111.8(4) . . ? C81 C8 C9 119.3(5) . . ? C8 C9 C5 103.6(4) . . ? C8 C9 C1 113.1(4) . . ? C5 C9 C1 113.6(4) . . ? O12 C11 O13 122.8(5) . . ? O12 C11 C1 125.2(5) . . ? O13 C11 C1 111.9(4) . . ? C11 O13 C14 116.9(4) . . ? C22 C21 C2 116.7(5) . . ? C21 C22 C23 112.0(6) . . ? C22 C23 C24 110.3(6) . . ? C25 C24 C23 116.7(10) . . ? C24 C25 C26 109.8(13) . . ? O42 C41 O43 122.3(5) . . ? O42 C41 C4 125.4(5) . . ? O43 C41 C4 112.2(5) . . ? O72 C71 O73 122.9(6) . . ? O72 C71 C7 123.0(6) . . ? O73 C71 C7 114.0(6) . . ? C71 O73 C74 115.3(6) . . ? C8 C81 C82 109.4(6) . . ? C83B C82 C81 109.7(10) . . ? C83B C82 C83A 30.2(10) . . ? C81 C82 C83A 95.8(9) . . ? C84A C83A C82 99.8(13) . . ? C85A C84A C83A 100.5(17) . . ? C84A C85A C86A 103.0(16) . . ? C84B C83B C82 104.8(7) . . ? C83B C84B C85B 123.4(5) . . ? C84B C85B C86B 115.61(14) . . ? _refine_diff_density_max 0.542 _refine_diff_density_min -0.556 _refine_diff_density_rms 0.064 data_29b _database_code_CSD 175318 _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'Whitehead, Roger C.' 'Al-Busafi, Saleh' 'Doncaster, Jeremy R.' 'Drew, M.' 'Regan, A.' _publ_contact_author_name 'Dr Roger C Whitehead' _publ_contact_author_address ; Department of Chemistry University of Manchester Oxford Road Manchester M13 9PL UNITED KINGDOM ; _publ_contact_author_email 'ROGER.WHITEHEAD@MAN.AC.UK' _publ_section_title ; Exploitation of Chemical Predisposition in Synthesis: An approach to the Manzamenones ; _publ_section_references ; Kabsch, W. (1988), J.Appl.Cryst 21 916-932. Sheldrick, G.M. (1990) SHELX86, Acta Cryst. A46 467-480. Sheldrick, G.M. (1993) SHELXL program for crystallography refinement. University of Gottingen, Germany. Spek, A.L., (1994) PLATON-94 program, Utrecht University, The Netherlands ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H22 O7' _chemical_formula_weight 350.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 11.628(13) _cell_length_b 11.417(12) _cell_length_c 14.112(15) _cell_angle_alpha 90.00 _cell_angle_beta 101.400(10) _cell_angle_gamma 90.00 _cell_volume 1837(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3401 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 26.10 _exptl_crystal_description misshapen _exptl_crystal_colour white _exptl_crystal_size_max 0.04 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.267 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 'Marresearch Image Plate' _diffrn_measurement_method '95 frames at 2^o intervals, counting time 2 min.' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3401 B _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1071 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.52 _diffrn_reflns_theta_max 26.10 _reflns_number_total 3401 _reflns_number_gt 1208 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XDS (Kabsch, 1991)' _computing_cell_refinement XDS _computing_data_reduction XDS _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'PLATON(Spek,1994)' _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 w=1/[\s^2^(Fo^2^)+(0.1463P)^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 3401 _refine_ls_number_parameters 231 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1905 _refine_ls_R_factor_gt 0.0897 _refine_ls_wR_factor_ref 0.2623 _refine_ls_wR_factor_gt 0.2198 _refine_ls_goodness_of_fit_ref 0.852 _refine_ls_restrained_S_all 0.852 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.0663(4) 0.8837(5) 0.3728(3) 0.0635(13) Uani 1 d . . . C2 C 0.9951(4) 0.9804(4) 0.3172(3) 0.0667(14) Uani 1 d . . . C3 C 0.8918(5) 0.9372(6) 0.2702(4) 0.0858(17) Uani 1 d . . . C4 C 0.8823(4) 0.8120(5) 0.2940(4) 0.0755(15) Uani 1 d . . . H4 H 0.8122 0.8027 0.3221 0.091 Uiso 1 calc R . . C5 C 0.8659(4) 0.7361(4) 0.2032(3) 0.0594(12) Uani 1 d . . . H5 H 0.7869 0.7476 0.1645 0.071 Uiso 1 calc R . . C6 C 0.8837(4) 0.6004(5) 0.2354(4) 0.0702(14) Uani 1 d . . . C7 C 0.9674(4) 0.5739(5) 0.3092(3) 0.0740(15) Uani 1 d . . . H7 H 0.9757 0.4961 0.3291 0.089 Uiso 1 calc R . . C8 C 1.0503(4) 0.6628(4) 0.3630(3) 0.0590(12) Uani 1 d . . . H8 H 1.1099 0.6779 0.3242 0.071 Uiso 1 calc R . . C9 C 0.9888(4) 0.7778(5) 0.3716(3) 0.0713(15) Uani 1 d . . . H9 H 0.9627 0.7765 0.4335 0.086 Uiso 1 calc R . . O11 O 1.1705(3) 0.8966(3) 0.4167(3) 0.0915(12) Uani 1 d . . . C21 C 1.0380(5) 1.1076(5) 0.3111(4) 0.0767(15) Uani 1 d . . . O23 O 1.1072(3) 1.1433(3) 0.3900(2) 0.0803(11) Uani 1 d . . . O22 O 1.0147(5) 1.1646(4) 0.2379(3) 0.1271(17) Uani 1 d . . . C24 C 1.1491(5) 1.2607(4) 0.3881(4) 0.0813(16) Uani 1 d . . . H24A H 1.0845 1.3142 0.3829 0.098 Uiso 1 calc R . . H24B H 1.1862 1.2705 0.3337 0.098 Uiso 1 calc R . . H24C H 1.2048 1.2763 0.4467 0.098 Uiso 1 calc R . . C31 C 0.7914(7) 1.0044(7) 0.2102(7) 0.145(3) Uani 1 d . . . H31A H 0.7183 0.9700 0.2198 0.174 Uiso 1 calc R . . H31B H 0.7939 1.0843 0.2339 0.174 Uiso 1 calc R . . C32 C 0.7908(11) 1.0070(8) 0.1187(9) 0.200(5) Uani 1 d . . . H32A H 0.7131 1.0249 0.0840 0.240 Uiso 1 calc R . . H32B H 0.8144 0.9320 0.0984 0.240 Uiso 1 calc R . . H32C H 0.8443 1.0660 0.1056 0.240 Uiso 1 calc R . . C51 C 0.9580(4) 0.7546(4) 0.1393(3) 0.0583(12) Uani 1 d . . . O52 O 1.0572(3) 0.7814(4) 0.1698(2) 0.0931(13) Uani 1 d . . . O53 O 0.9134(3) 0.7399(4) 0.0478(2) 0.1040(15) Uani 1 d . . . C54 C 0.9991(7) 0.7508(8) -0.0151(4) 0.153(4) Uani 1 d . . . H54A H 0.9608 0.7377 -0.0810 0.183 Uiso 1 calc R . . H54B H 1.0601 0.6938 0.0033 0.183 Uiso 1 calc R . . H54C H 1.0325 0.8280 -0.0088 0.183 Uiso 1 calc R . . C61 C 0.7982(5) 0.5143(5) 0.1772(5) 0.0935(18) Uani 1 d . . . H61A H 0.7199 0.5332 0.1867 0.112 Uiso 1 calc R . . H61B H 0.7990 0.5258 0.1092 0.112 Uiso 1 calc R . . C62 C 0.8197(7) 0.3939(7) 0.1995(5) 0.135(3) Uani 1 d . . . H62A H 0.7548 0.3480 0.1665 0.162 Uiso 1 calc R . . H62B H 0.8289 0.3825 0.2680 0.162 Uiso 1 calc R . . H62C H 0.8901 0.3699 0.1790 0.162 Uiso 1 calc R . . C81 C 1.1132(5) 0.6183(5) 0.4583(4) 0.0728(14) Uani 1 d . . . O82 O 1.0883(4) 0.6409(4) 0.5362(3) 0.0969(13) Uani 1 d . . . O83 O 1.1972(4) 0.5473(4) 0.4478(3) 0.0953(12) Uani 1 d . . . H83 H 1.2339 0.5276 0.5012 0.114 Uiso 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 C1 0.063(3) 0.078(4) 0.047(2) 0.007(2) 0.005(2) 0.005(3) C2 0.068(3) 0.072(4) 0.063(3) 0.011(2) 0.019(3) 0.026(3) C3 0.065(4) 0.089(4) 0.098(4) 0.030(3) 0.002(3) 0.019(3) C4 0.051(3) 0.091(4) 0.084(3) 0.008(3) 0.010(3) 0.013(3) C5 0.043(2) 0.060(3) 0.070(3) 0.000(2) -0.001(2) -0.009(2) C6 0.045(3) 0.071(4) 0.096(4) -0.029(3) 0.018(3) -0.021(3) C7 0.074(4) 0.089(4) 0.057(3) -0.005(3) 0.008(3) -0.026(3) C8 0.053(3) 0.068(3) 0.057(3) -0.008(2) 0.013(2) -0.014(3) C9 0.053(3) 0.114(5) 0.047(2) 0.005(3) 0.008(2) 0.005(3) O11 0.088(3) 0.066(2) 0.104(3) 0.026(2) -0.019(2) 0.009(2) C21 0.094(4) 0.068(4) 0.064(3) 0.011(3) 0.006(3) 0.017(3) O23 0.095(3) 0.053(2) 0.081(2) 0.0041(17) -0.012(2) -0.0088(19) O22 0.175(5) 0.087(3) 0.099(3) 0.018(3) -0.023(3) 0.002(3) C24 0.093(4) 0.055(4) 0.086(3) -0.003(3) -0.006(3) -0.008(3) C31 0.133(6) 0.094(6) 0.166(7) 0.043(5) -0.069(6) 0.016(5) C32 0.257(13) 0.112(8) 0.191(10) 0.026(7) -0.051(10) 0.013(8) C51 0.063(3) 0.045(3) 0.065(3) 0.009(2) 0.010(2) 0.005(2) O52 0.054(2) 0.158(4) 0.068(2) 0.012(2) 0.0133(18) -0.006(2) O53 0.089(3) 0.166(4) 0.0498(19) 0.002(2) -0.0015(19) -0.018(3) C54 0.141(6) 0.264(11) 0.063(3) -0.002(4) 0.048(4) -0.016(6) C61 0.062(4) 0.061(4) 0.146(5) 0.011(4) -0.008(3) 0.003(3) C62 0.108(6) 0.150(8) 0.132(6) -0.018(5) -0.011(4) -0.018(6) C81 0.081(4) 0.046(3) 0.079(4) 0.005(3) -0.015(3) -0.011(3) O82 0.116(3) 0.111(3) 0.065(2) 0.018(2) 0.020(2) 0.010(3) O83 0.104(3) 0.090(3) 0.084(2) -0.014(2) -0.001(2) 0.024(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 C1 O11 1.257(6) . ? C1 C2 1.505(7) . ? C1 C9 1.505(7) . ? C2 C3 1.346(7) . ? C2 C21 1.543(8) . ? C3 C4 1.478(8) . ? C3 C31 1.509(8) . ? C4 C5 1.527(7) . ? C4 C9 1.532(6) . ? C5 C51 1.544(6) . ? C5 C6 1.617(7) . ? C6 C7 1.313(7) . ? C6 C61 1.519(7) . ? C7 C8 1.499(6) . ? C8 C81 1.487(7) . ? C8 C9 1.511(7) . ? C21 O22 1.205(6) . ? C21 O23 1.304(6) . ? O23 C24 1.428(6) . ? C31 C32 1.290(12) . ? C51 O52 1.189(5) . ? C51 O53 1.304(5) . ? O53 C54 1.465(7) . ? C61 C62 1.422(9) . ? C81 O82 1.218(6) . ? C81 O83 1.301(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O11 C1 C2 123.3(5) . . ? O11 C1 C9 128.1(5) . . ? C2 C1 C9 108.5(4) . . ? C3 C2 C1 109.5(5) . . ? C3 C2 C21 125.8(5) . . ? C1 C2 C21 124.7(5) . . ? C2 C3 C4 110.0(5) . . ? C2 C3 C31 127.3(6) . . ? C4 C3 C31 122.3(6) . . ? C3 C4 C5 111.2(4) . . ? C3 C4 C9 108.8(5) . . ? C5 C4 C9 113.9(4) . . ? C4 C5 C51 115.2(4) . . ? C4 C5 C6 108.7(4) . . ? C51 C5 C6 103.3(3) . . ? C7 C6 C61 125.7(5) . . ? C7 C6 C5 118.6(4) . . ? C61 C6 C5 115.7(4) . . ? C6 C7 C8 123.2(5) . . ? C81 C8 C7 112.2(4) . . ? C81 C8 C9 112.4(4) . . ? C7 C8 C9 111.2(4) . . ? C1 C9 C8 114.0(4) . . ? C1 C9 C4 101.6(4) . . ? C8 C9 C4 119.5(4) . . ? O22 C21 O23 124.0(6) . . ? O22 C21 C2 122.4(5) . . ? O23 C21 C2 113.5(4) . . ? C21 O23 C24 115.7(4) . . ? C32 C31 C3 115.1(10) . . ? O52 C51 O53 124.0(4) . . ? O52 C51 C5 124.0(4) . . ? O53 C51 C5 112.0(4) . . ? C51 O53 C54 113.9(4) . . ? C62 C61 C6 116.0(5) . . ? O82 C81 O83 123.5(5) . . ? O82 C81 C8 125.5(6) . . ? O83 C81 C8 110.9(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 O11 C1 C2 C3 173.8(5) . . . . ? C9 C1 C2 C3 -10.4(5) . . . . ? O11 C1 C2 C21 -3.1(7) . . . . ? C9 C1 C2 C21 172.7(4) . . . . ? C1 C2 C3 C4 3.0(6) . . . . ? C21 C2 C3 C4 179.8(4) . . . . ? C1 C2 C3 C31 176.6(6) . . . . ? C21 C2 C3 C31 -6.6(9) . . . . ? C2 C3 C4 C5 -120.8(5) . . . . ? C31 C3 C4 C5 65.2(7) . . . . ? C2 C3 C4 C9 5.4(6) . . . . ? C31 C3 C4 C9 -168.6(6) . . . . ? C3 C4 C5 C51 52.9(6) . . . . ? C9 C4 C5 C51 -70.5(5) . . . . ? C3 C4 C5 C6 168.1(4) . . . . ? C9 C4 C5 C6 44.8(5) . . . . ? C4 C5 C6 C7 -40.0(5) . . . . ? C51 C5 C6 C7 82.8(5) . . . . ? C4 C5 C6 C61 138.8(4) . . . . ? C51 C5 C6 C61 -98.4(5) . . . . ? C61 C6 C7 C8 179.2(4) . . . . ? C5 C6 C7 C8 -2.2(7) . . . . ? C6 C7 C8 C81 163.8(5) . . . . ? C6 C7 C8 C9 36.9(6) . . . . ? O11 C1 C9 C8 -41.9(7) . . . . ? C2 C1 C9 C8 142.5(4) . . . . ? O11 C1 C9 C4 -171.8(5) . . . . ? C2 C1 C9 C4 12.6(5) . . . . ? C81 C8 C9 C1 84.7(5) . . . . ? C7 C8 C9 C1 -148.4(4) . . . . ? C81 C8 C9 C4 -154.9(4) . . . . ? C7 C8 C9 C4 -28.1(6) . . . . ? C3 C4 C9 C1 -11.0(5) . . . . ? C5 C4 C9 C1 113.6(5) . . . . ? C3 C4 C9 C8 -137.4(5) . . . . ? C5 C4 C9 C8 -12.8(6) . . . . ? C3 C2 C21 O22 -34.6(8) . . . . ? C1 C2 C21 O22 141.8(6) . . . . ? C3 C2 C21 O23 149.7(5) . . . . ? C1 C2 C21 O23 -34.0(6) . . . . ? O22 C21 O23 C24 4.5(8) . . . . ? C2 C21 O23 C24 -179.9(4) . . . . ? C2 C3 C31 C32 94.4(10) . . . . ? C4 C3 C31 C32 -92.7(10) . . . . ? C4 C5 C51 O52 31.4(7) . . . . ? C6 C5 C51 O52 -86.9(6) . . . . ? C4 C5 C51 O53 -147.0(4) . . . . ? C6 C5 C51 O53 94.7(4) . . . . ? O52 C51 O53 C54 4.5(8) . . . . ? C5 C51 O53 C54 -177.1(5) . . . . ? C7 C6 C61 C62 -6.8(9) . . . . ? C5 C6 C61 C62 174.6(5) . . . . ? C7 C8 C81 O82 -100.5(6) . . . . ? C9 C8 C81 O82 25.8(7) . . . . ? C7 C8 C81 O83 77.1(5) . . . . ? C9 C8 C81 O83 -156.6(4) . . . . ? _refine_diff_density_max 0.566 _refine_diff_density_min -0.268 _refine_diff_density_rms 0.075