Supplementary Material for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? #------------------------------------------------------------------------------ _publ_section_title ;Synthesis of 5-hydroxy-2,3,4,5-tetrahydro-[1H]-2-benzazepin-4-ones; selective antagonists of muscarinic (M3) receptors ; _publ_contact_author_name 'Prof. E.J.Thomas' _publ_contact_author_email E.J.THOMAS@MANCHESTER.AC.UK loop_ _publ_author_name E.J.Thomas 'Benjamin C. P. Allen' 'Ben Bradshaw' 'Kenneth J. Broadley' 'Robin H. Davies' ; C.Escargueil ; 'Paul Evans' 'Jane Fletcher' 'Amar Hamrouni' 'Alan T. L. Lee' 'Paul G. Mwashimba' ; D.Oehlrich ; data_S804 _database_code_depnum_ccdc_archive 'CCDC 655337' #------------------------------------------------------------------------------ _audit_creation_date 19100-03-07 _audit_creation_method 'by teXsan v1.7' _audit_update_record ; ? ; _publ_section_exptl_refinement ; Non H atoms were refined anisotropically and H atoms were refined isotropically. ; _publ_section_references ; Molecular Structure Corporation. (1995). teXsan. Single Crystal Structure Analysis Software. Version 1.7. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Sheldrick, G.M. (1985). In: "Crystallographic Computing 3" (Eds G.M. Sheldrick, C. Kruger and R. Goddard) Oxford University Press, pp. 175-189. ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H25 N O2 S2' _chemical_formula_weight 351.51 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 '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/n ' _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall ? 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 10.712(6) _cell_length_b 11.368(4) _cell_length_c 15.945(4) _cell_angle_alpha 90.00 _cell_angle_beta 103.78(3) _cell_angle_gamma 90.00 _cell_volume 1885.6(13) _cell_formula_units_Z 4 _cell_measurement_temperature 296.2 _cell_measurement_reflns_used 20 _cell_measurement_theta_min 14.8 _cell_measurement_theta_max 16.8 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.38 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.238 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 2.621 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 ; _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.809 _exptl_special_details ; The scan width was (0.84+0.30tan\q)\% with an \w scan speed of 8\% per minute (up to 4 scans to achieve I/\s(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1. ; #------------------------------------------------------------------------------ _diffrn_special_details ; ? ; _diffrn_ambient_temperature 296.2 _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device 'Rigaku AFC5R' _diffrn_measurement_method \w-2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 3.31 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -3 -2 1 -3 -2 0 0 -1 -5 _diffrn_reflns_number 7554 _diffrn_reflns_av_R_equivalents 0.0402 _diffrn_reflns_av_sigmaI/netI 0.0412 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 4.52 _diffrn_reflns_theta_max 72.11 _reflns_number_total 3619 _reflns_number_gt 2942 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan (MSC, 1995)' _computing_structure_solution ; SHELXS86 (Sheldrick, 1985) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'teXsan (MSC, 1995)' _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^)+(0.0647P)^2^+1.4011P] 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 0.0228(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3619 _refine_ls_number_parameters 309 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0677 _refine_ls_R_factor_gt 0.0546 _refine_ls_wR_factor_ref 0.1688 _refine_ls_wR_factor_gt 0.1520 _refine_ls_goodness_of_fit_ref 1.147 _refine_ls_restrained_S_all 1.147 _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 S1 S 0.13967(7) 0.42337(7) 0.03590(5) 0.0545(3) Uani 1 d . . . S2 S 0.41543(8) 0.33929(8) 0.07007(6) 0.0655(3) Uani 1 d . . . O1 O 0.1365(2) 0.4800(2) 0.25929(15) 0.0641(6) Uani 1 d . . . O2 O -0.0272(2) 0.3496(2) 0.25130(16) 0.0645(6) Uani 1 d . . . N1 N 0.1511(2) 0.2906(2) 0.21525(15) 0.0512(6) Uani 1 d . . . C1 C 0.0916(3) 0.1751(3) 0.1957(2) 0.0567(8) Uani 1 d . . . H1A H 0.041(3) 0.158(3) 0.238(2) 0.057(9) Uiso 1 d . . . H1B H 0.162(4) 0.115(3) 0.206(2) 0.068(10) Uiso 1 d . . . C2 C 0.0113(3) 0.1622(2) 0.1050(2) 0.0512(7) Uani 1 d . . . C3 C -0.1204(3) 0.1407(3) 0.0899(3) 0.0632(8) Uani 1 d . . . H3 H -0.160(4) 0.135(3) 0.144(2) 0.073(11) Uiso 1 d . . . C4 C -0.1947(4) 0.1249(3) 0.0067(3) 0.0702(10) Uani 1 d . . . H4 H -0.291(5) 0.107(4) -0.002(3) 0.102(14) Uiso 1 d . . . C5 C -0.1382(4) 0.1306(3) -0.0618(3) 0.0708(10) Uani 1 d . . . H5 H -0.186(4) 0.120(4) -0.116(3) 0.084(13) Uiso 1 d . . . C6 C -0.0083(4) 0.1541(3) -0.0484(2) 0.0625(8) Uani 1 d . . . H6 H 0.037(4) 0.160(3) -0.097(3) 0.074(11) Uiso 1 d . . . C7 C 0.0684(3) 0.1697(3) 0.0346(2) 0.0523(7) Uani 1 d . . . C8 C 0.2107(3) 0.1951(3) 0.0478(2) 0.0586(8) Uani 1 d . . . H8A H 0.229(4) 0.194(3) -0.012(3) 0.079(11) Uiso 1 d . . . H8B H 0.264(3) 0.133(3) 0.083(2) 0.061(9) Uiso 1 d . . . C9 C 0.2558(3) 0.3145(3) 0.0906(2) 0.0525(7) Uani 1 d . . . C10 C 0.2709(3) 0.3114(3) 0.1893(2) 0.0541(7) Uani 1 d . . . H10A H 0.340(3) 0.247(3) 0.215(2) 0.062(9) Uiso 1 d . . . H10B H 0.309(3) 0.388(3) 0.215(2) 0.061(9) Uiso 1 d . . . C11 C 0.0899(3) 0.3823(3) 0.24220(19) 0.0512(7) Uani 1 d . . . C12 C -0.1127(3) 0.4331(3) 0.2805(2) 0.0648(9) Uani 1 d . . . C13 C -0.1430(6) 0.5363(6) 0.2198(5) 0.1033(17) Uani 1 d . . . H13A H -0.071(6) 0.589(6) 0.222(4) 0.14(2) Uiso 1 d . . . H13B H -0.220(6) 0.580(6) 0.226(4) 0.15(2) Uiso 1 d . . . H13C H -0.172(6) 0.495(6) 0.166(4) 0.14(3) Uiso 1 d . . . C14 C -0.0525(5) 0.4690(7) 0.3728(3) 0.0979(17) Uani 1 d . . . H14A H -0.023(7) 0.396(8) 0.412(5) 0.19(3) Uiso 1 d . . . H14B H -0.103(6) 0.515(6) 0.396(4) 0.14(2) Uiso 1 d . . . H14C H 0.026(5) 0.518(5) 0.377(3) 0.114(17) Uiso 1 d . . . C15 C -0.2315(5) 0.3600(6) 0.2780(5) 0.0972(16) Uani 1 d . . . H15A H -0.262(5) 0.338(5) 0.222(4) 0.111(19) Uiso 1 d . . . H15B H -0.297(5) 0.406(5) 0.299(3) 0.118(17) Uiso 1 d . . . H15C H -0.211(5) 0.283(6) 0.314(4) 0.14(2) Uiso 1 d . . . C16 C 0.2170(4) 0.5609(3) 0.0773(3) 0.0636(9) Uani 1 d . . . H16A H 0.154(4) 0.619(4) 0.044(2) 0.074(11) Uiso 1 d . . . H16B H 0.211(3) 0.568(3) 0.140(2) 0.059(9) Uiso 1 d . . . C17 C 0.3487(4) 0.5793(4) 0.0608(3) 0.0726(10) Uani 1 d . . . H17A H 0.339(3) 0.580(3) 0.001(3) 0.064(10) Uiso 1 d . . . H17B H 0.383(4) 0.658(4) 0.082(3) 0.086(13) Uiso 1 d . . . C18 C 0.4472(4) 0.4908(4) 0.1059(3) 0.0707(10) Uani 1 d . . . H18A H 0.460(3) 0.491(3) 0.171(2) 0.071(11) Uiso 1 d . . . H18B H 0.528(4) 0.506(4) 0.097(3) 0.086(13) Uiso 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0525(5) 0.0524(5) 0.0565(5) 0.0020(3) 0.0085(3) 0.0005(3) S2 0.0533(5) 0.0689(6) 0.0807(6) -0.0125(4) 0.0285(4) 0.0003(4) O1 0.0615(13) 0.0658(15) 0.0680(14) -0.0146(11) 0.0215(11) -0.0107(11) O2 0.0546(13) 0.0635(14) 0.0817(16) -0.0112(11) 0.0288(11) -0.0054(10) N1 0.0502(13) 0.0574(14) 0.0466(13) -0.0007(11) 0.0130(10) 0.0011(11) C1 0.0629(19) 0.0534(18) 0.0555(18) 0.0076(14) 0.0177(15) 0.0025(15) C2 0.0543(17) 0.0400(14) 0.0603(17) 0.0002(12) 0.0159(14) 0.0008(12) C3 0.063(2) 0.0523(18) 0.076(2) 0.0026(16) 0.0200(17) -0.0067(15) C4 0.060(2) 0.059(2) 0.086(3) 0.0006(18) 0.0077(19) -0.0112(16) C5 0.074(2) 0.061(2) 0.066(2) -0.0012(17) -0.0039(19) -0.0100(17) C6 0.073(2) 0.0558(19) 0.0585(19) -0.0047(15) 0.0144(17) -0.0044(15) C7 0.0580(17) 0.0424(15) 0.0571(17) -0.0028(12) 0.0148(14) -0.0005(12) C8 0.0588(19) 0.0590(19) 0.0617(19) -0.0068(15) 0.0217(15) 0.0029(15) C9 0.0535(16) 0.0538(17) 0.0521(16) -0.0064(13) 0.0163(13) 0.0032(13) C10 0.0428(15) 0.0645(19) 0.0531(17) -0.0029(14) 0.0077(13) 0.0029(14) C11 0.0474(15) 0.0592(18) 0.0472(15) -0.0032(13) 0.0116(12) -0.0023(13) C12 0.0542(18) 0.071(2) 0.073(2) -0.0075(17) 0.0217(16) 0.0057(15) C13 0.086(4) 0.101(4) 0.124(5) 0.028(4) 0.028(3) 0.024(3) C14 0.077(3) 0.141(5) 0.082(3) -0.035(3) 0.032(2) 0.001(3) C15 0.064(3) 0.105(4) 0.133(5) -0.021(4) 0.045(3) -0.010(2) C16 0.060(2) 0.0566(19) 0.076(2) -0.0014(17) 0.0202(17) -0.0010(15) C17 0.074(2) 0.062(2) 0.087(3) -0.0057(19) 0.031(2) -0.0147(18) C18 0.056(2) 0.078(3) 0.083(3) -0.011(2) 0.0274(18) -0.0108(17) _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 S1 C16 1.818(4) . ? S1 C9 1.823(3) . ? S2 C18 1.821(4) . ? S2 C9 1.838(3) . ? O1 C11 1.221(4) . ? O2 C11 1.350(4) . ? O2 C12 1.470(4) . ? N1 C11 1.355(4) . ? N1 C10 1.459(4) . ? N1 C1 1.460(4) . ? C1 C2 1.503(5) . ? C1 H1A 0.99(3) . ? C1 H1B 1.00(4) . ? C2 C3 1.396(5) . ? C2 C7 1.403(4) . ? C3 C4 1.386(5) . ? C3 H3 1.04(4) . ? C4 C5 1.371(6) . ? C4 H4 1.03(5) . ? C5 C6 1.383(5) . ? C5 H5 0.90(4) . ? C6 C7 1.393(5) . ? C6 H6 1.01(4) . ? C7 C8 1.515(5) . ? C8 C9 1.545(4) . ? C8 H8A 1.01(4) . ? C8 H8B 0.99(4) . ? C9 C10 1.544(4) . ? C10 H10A 1.06(4) . ? C10 H10B 1.00(4) . ? C12 C13 1.506(7) . ? C12 C15 1.512(6) . ? C12 C14 1.515(6) . ? C13 H13A 0.97(7) . ? C13 H13B 0.99(7) . ? C13 H13C 0.96(7) . ? C14 H14A 1.04(8) . ? C14 H14B 0.90(6) . ? C14 H14C 1.00(6) . ? C15 H15A 0.91(6) . ? C15 H15B 1.00(5) . ? C15 H15C 1.04(7) . ? C16 C17 1.509(5) . ? C16 H16A 1.00(4) . ? C16 H16B 1.02(4) . ? C17 C18 1.510(6) . ? C17 H17A 0.94(4) . ? C17 H17B 1.00(4) . ? C18 H18A 1.02(4) . ? C18 H18B 0.93(4) . ? 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 C16 S1 C9 102.13(17) . . ? C18 S2 C9 101.58(16) . . ? C11 O2 C12 121.4(3) . . ? C11 N1 C10 119.3(3) . . ? C11 N1 C1 122.8(3) . . ? C10 N1 C1 117.0(3) . . ? N1 C1 C2 114.4(3) . . ? N1 C1 H1A 108.0(19) . . ? C2 C1 H1A 111.3(19) . . ? N1 C1 H1B 107(2) . . ? C2 C1 H1B 109(2) . . ? H1A C1 H1B 106(3) . . ? C3 C2 C7 119.3(3) . . ? C3 C2 C1 120.4(3) . . ? C7 C2 C1 120.3(3) . . ? C4 C3 C2 120.9(4) . . ? C4 C3 H3 122(2) . . ? C2 C3 H3 117(2) . . ? C5 C4 C3 119.6(4) . . ? C5 C4 H4 121(3) . . ? C3 C4 H4 119(3) . . ? C4 C5 C6 120.4(4) . . ? C4 C5 H5 120(3) . . ? C6 C5 H5 120(3) . . ? C5 C6 C7 121.0(4) . . ? C5 C6 H6 123(2) . . ? C7 C6 H6 116(2) . . ? C6 C7 C2 118.8(3) . . ? C6 C7 C8 120.1(3) . . ? C2 C7 C8 121.1(3) . . ? C7 C8 C9 115.3(3) . . ? C7 C8 H8A 106(2) . . ? C9 C8 H8A 108(2) . . ? C7 C8 H8B 112(2) . . ? C9 C8 H8B 107(2) . . ? H8A C8 H8B 108(3) . . ? C10 C9 C8 112.1(3) . . ? C10 C9 S1 113.4(2) . . ? C8 C9 S1 106.2(2) . . ? C10 C9 S2 108.0(2) . . ? C8 C9 S2 105.2(2) . . ? S1 C9 S2 111.63(17) . . ? N1 C10 C9 114.0(2) . . ? N1 C10 H10A 111.3(18) . . ? C9 C10 H10A 108.0(18) . . ? N1 C10 H10B 109(2) . . ? C9 C10 H10B 109(2) . . ? H10A C10 H10B 105(3) . . ? O1 C11 O2 124.6(3) . . ? O1 C11 N1 124.6(3) . . ? O2 C11 N1 110.7(3) . . ? O2 C12 C13 110.7(4) . . ? O2 C12 C15 102.7(3) . . ? C13 C12 C15 111.1(5) . . ? O2 C12 C14 109.2(3) . . ? C13 C12 C14 113.0(5) . . ? C15 C12 C14 109.6(4) . . ? C12 C13 H13A 114(4) . . ? C12 C13 H13B 113(4) . . ? H13A C13 H13B 111(5) . . ? C12 C13 H13C 99(4) . . ? H13A C13 H13C 115(6) . . ? H13B C13 H13C 103(5) . . ? C12 C14 H14A 112(5) . . ? C12 C14 H14B 114(4) . . ? H14A C14 H14B 110(6) . . ? C12 C14 H14C 112(3) . . ? H14A C14 H14C 106(5) . . ? H14B C14 H14C 104(5) . . ? C12 C15 H15A 106(3) . . ? C12 C15 H15B 111(3) . . ? H15A C15 H15B 112(5) . . ? C12 C15 H15C 113(3) . . ? H15A C15 H15C 107(5) . . ? H15B C15 H15C 109(5) . . ? C17 C16 S1 114.8(3) . . ? C17 C16 H16A 111(2) . . ? S1 C16 H16A 100(2) . . ? C17 C16 H16B 116.3(19) . . ? S1 C16 H16B 106.9(19) . . ? H16A C16 H16B 106(3) . . ? C16 C17 C18 113.6(3) . . ? C16 C17 H17A 108(2) . . ? C18 C17 H17A 112(2) . . ? C16 C17 H17B 111(3) . . ? C18 C17 H17B 106(2) . . ? H17A C17 H17B 106(3) . . ? C17 C18 S2 115.1(3) . . ? C17 C18 H18A 113(2) . . ? S2 C18 H18A 107(2) . . ? C17 C18 H18B 112(3) . . ? S2 C18 H18B 104(3) . . ? H18A C18 H18B 105(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 C11 N1 C1 C2 86.0(4) . . . . ? C10 N1 C1 C2 -82.7(3) . . . . ? N1 C1 C2 C3 -117.0(3) . . . . ? N1 C1 C2 C7 64.1(4) . . . . ? C7 C2 C3 C4 1.0(5) . . . . ? C1 C2 C3 C4 -177.9(3) . . . . ? C2 C3 C4 C5 -0.1(5) . . . . ? C3 C4 C5 C6 -1.1(6) . . . . ? C4 C5 C6 C7 1.5(6) . . . . ? C5 C6 C7 C2 -0.5(5) . . . . ? C5 C6 C7 C8 179.9(3) . . . . ? C3 C2 C7 C6 -0.7(4) . . . . ? C1 C2 C7 C6 178.2(3) . . . . ? C3 C2 C7 C8 178.9(3) . . . . ? C1 C2 C7 C8 -2.2(4) . . . . ? C6 C7 C8 C9 118.2(3) . . . . ? C2 C7 C8 C9 -61.4(4) . . . . ? C7 C8 C9 C10 78.6(4) . . . . ? C7 C8 C9 S1 -45.8(3) . . . . ? C7 C8 C9 S2 -164.3(2) . . . . ? C16 S1 C9 C10 66.2(3) . . . . ? C16 S1 C9 C8 -170.2(2) . . . . ? C16 S1 C9 S2 -56.1(2) . . . . ? C18 S2 C9 C10 -69.5(3) . . . . ? C18 S2 C9 C8 170.6(2) . . . . ? C18 S2 C9 S1 55.9(2) . . . . ? C11 N1 C10 C9 -102.0(3) . . . . ? C1 N1 C10 C9 67.1(4) . . . . ? C8 C9 C10 N1 -63.8(4) . . . . ? S1 C9 C10 N1 56.5(3) . . . . ? S2 C9 C10 N1 -179.2(2) . . . . ? C12 O2 C11 O1 2.3(5) . . . . ? C12 O2 C11 N1 179.6(3) . . . . ? C10 N1 C11 O1 -11.7(4) . . . . ? C1 N1 C11 O1 179.9(3) . . . . ? C10 N1 C11 O2 171.1(2) . . . . ? C1 N1 C11 O2 2.6(4) . . . . ? C11 O2 C12 C13 59.5(5) . . . . ? C11 O2 C12 C15 178.2(4) . . . . ? C11 O2 C12 C14 -65.6(5) . . . . ? C9 S1 C16 C17 58.0(3) . . . . ? S1 C16 C17 C18 -64.2(5) . . . . ? C16 C17 C18 S2 64.4(4) . . . . ? C9 S2 C18 C17 -57.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.928 _diffrn_reflns_theta_full 72.11 _diffrn_measured_fraction_theta_full 0.928 _refine_diff_density_max 0.305 _refine_diff_density_min -0.370 _refine_diff_density_rms 0.058 # Attachment 'OBC_1_53.cif1.save' data_s862 _database_code_depnum_ccdc_archive 'CCDC 655338' _audit_creation_method 'WinGX routine-INITIALISE' _audit_creation_date 2000-09-02T09:14:36-00:00 _chemical_name_systematic ; ? ; _publ_section_exptl_refinement ; The structure was solved by direct methods. Non-H atoms were refined anisotropically and H atoms bonded to C were included in calculated positions. Hydroxyl H atoms were found by difference Fourier techniques and refined isotropically. H-bonding interactions are as follows: Hydrogen bonds with H..A < r(A) + 2.000 Angstroms and 110 deg. D-H d(D-H) d(H..A) 2sigma(I) _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution ; SHELXS86 (Sheldrick, 1985) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'teXsan (MSC, 1995)' _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^)+(0.0479P)^2^+0.2830P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2860 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1167 _refine_ls_R_factor_gt 0.0562 _refine_ls_wR_factor_ref 0.1409 _refine_ls_wR_factor_gt 0.1095 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 O1 O 0.1227(3) 0.2176(3) 0.1813(2) 0.0548(6) Uani 1 d . . . H1 H 0.101(5) 0.162(4) 0.110(3) 0.077(13) Uiso 1 d . . . O2 O -0.1800(3) -0.0272(3) 0.0367(2) 0.0627(7) Uani 1 d . . . H2 H -0.289(5) -0.026(4) 0.022(3) 0.087(14) Uiso 1 d . . . N1 N -0.4214(3) -0.0023(2) 0.1724(2) 0.0456(6) Uani 1 d . . . C1 C -0.4234(4) 0.1522(3) 0.2412(3) 0.0431(7) Uani 1 d . . . H1A H -0.3570 0.1813 0.3279 0.052 Uiso 1 calc R . . H1B H -0.5486 0.1578 0.2358 0.052 Uiso 1 calc R . . C2 C -0.3428(4) 0.2628(3) 0.1973(2) 0.0387(7) Uani 1 d . . . C3 C -0.4508(4) 0.3543(3) 0.1691(3) 0.0501(8) Uani 1 d . . . H3 H -0.5682 0.3412 0.1751 0.060 Uiso 1 calc R . . C4 C -0.3911(5) 0.4637(3) 0.1326(3) 0.0585(9) Uani 1 d . . . H4 H -0.4659 0.5249 0.1160 0.070 Uiso 1 calc R . . C5 C -0.2209(5) 0.4815(4) 0.1208(3) 0.0606(9) Uani 1 d . . . H5 H -0.1793 0.5548 0.0955 0.073 Uiso 1 calc R . . C6 C -0.1107(4) 0.3912(3) 0.1463(3) 0.0524(8) Uani 1 d . . . H6 H 0.0044 0.4036 0.1366 0.063 Uiso 1 calc R . . C7 C -0.1662(4) 0.2819(3) 0.1862(2) 0.0405(7) Uani 1 d . . . C8 C -0.0310(3) 0.1950(3) 0.2229(2) 0.0412(7) Uani 1 d . . . C9 C -0.1080(4) 0.0261(3) 0.1678(3) 0.0497(8) Uani 1 d . . . H9 H -0.0043 -0.0184 0.1845 0.060 Uiso 1 calc R . . C10 C -0.2479(4) -0.0354(3) 0.2162(3) 0.0496(8) Uani 1 d . . . H10A H -0.2632 -0.1427 0.1884 0.060 Uiso 1 calc R . . H10B H -0.2056 0.0085 0.3062 0.060 Uiso 1 calc R . . C11 C -0.5748(4) -0.1111(3) 0.1661(3) 0.0537(8) Uani 1 d . . . H11A H -0.5750 -0.2087 0.1077 0.064 Uiso 1 calc R . . H11B H -0.6865 -0.0861 0.1322 0.064 Uiso 1 calc R . . C12 C -0.5795(4) -0.1237(3) 0.2859(3) 0.0551(8) Uani 1 d . . . H12A H -0.5731 -0.0260 0.3470 0.066 Uiso 1 calc R . . H12B H -0.4739 -0.1574 0.3175 0.066 Uiso 1 calc R . . C13 C -0.7513(5) -0.2320(4) 0.2683(3) 0.0703(10) Uani 1 d . . . H13A H -0.8555 -0.2093 0.2220 0.084 Uiso 1 calc R . . H13B H -0.7462 -0.3326 0.2190 0.084 Uiso 1 calc R . . C14 C -0.7786(6) -0.2276(4) 0.3865(4) 0.0932(13) Uani 1 d . . . H14A H -0.6772 -0.2519 0.4324 0.140 Uiso 1 calc R . . H14B H -0.8887 -0.2989 0.3688 0.140 Uiso 1 calc R . . H14C H -0.7877 -0.1292 0.4348 0.140 Uiso 1 calc R . . C15 C 0.0438(4) 0.2593(3) 0.3641(2) 0.0450(7) Uani 1 d . . . H15 H -0.0575 0.2612 0.3990 0.054 Uiso 1 calc R . . C16 C 0.1802(4) 0.4118(4) 0.4309(3) 0.0628(9) Uani 1 d . . . H16A H 0.2497 0.4354 0.3808 0.075 Uiso 1 calc R . . H16B H 0.1276 0.4936 0.4687 0.075 Uiso 1 calc R . . C17 C 0.2813(6) 0.3537(5) 0.5208(4) 0.1017(14) Uani 1 d . . . H17A H 0.2504 0.3817 0.5976 0.122 Uiso 1 calc R . . H17B H 0.4123 0.3767 0.5373 0.122 Uiso 1 calc R . . C18 C 0.1865(5) 0.1957(4) 0.4285(3) 0.0706(10) Uani 1 d . . . H18A H 0.1382 0.1321 0.4648 0.085 Uiso 1 calc R . . H18B H 0.2580 0.1476 0.3776 0.085 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 O1 0.0363(12) 0.0638(14) 0.0489(14) 0.0024(11) 0.0229(10) 0.0010(10) O2 0.0467(15) 0.0677(15) 0.0495(14) -0.0047(11) 0.0234(11) -0.0002(12) N1 0.0414(14) 0.0439(14) 0.0468(14) 0.0138(12) 0.0167(11) 0.0012(11) C1 0.0359(16) 0.0489(18) 0.0463(17) 0.0168(14) 0.0186(13) 0.0115(13) C2 0.0378(16) 0.0405(16) 0.0343(15) 0.0106(13) 0.0127(12) 0.0075(13) C3 0.0422(17) 0.0519(19) 0.0496(18) 0.0163(15) 0.0108(14) 0.0073(15) C4 0.060(2) 0.051(2) 0.058(2) 0.0211(16) 0.0100(17) 0.0117(17) C5 0.069(2) 0.052(2) 0.060(2) 0.0285(17) 0.0157(18) 0.0027(18) C6 0.0459(18) 0.0548(19) 0.0495(18) 0.0167(16) 0.0167(15) -0.0028(16) C7 0.0355(16) 0.0432(16) 0.0327(15) 0.0069(13) 0.0114(12) -0.0017(13) C8 0.0296(15) 0.0467(17) 0.0422(16) 0.0092(13) 0.0171(13) 0.0060(13) C9 0.0413(17) 0.0486(18) 0.0517(19) 0.0074(15) 0.0201(15) 0.0122(14) C10 0.0490(18) 0.0408(17) 0.0606(19) 0.0160(15) 0.0255(15) 0.0124(14) C11 0.0474(18) 0.0513(19) 0.0536(19) 0.0162(15) 0.0143(15) -0.0011(15) C12 0.055(2) 0.0508(19) 0.0574(19) 0.0215(16) 0.0185(16) 0.0040(15) C13 0.065(2) 0.065(2) 0.082(3) 0.035(2) 0.0262(19) -0.0025(18) C14 0.115(4) 0.080(3) 0.101(3) 0.044(2) 0.059(3) 0.006(2) C15 0.0359(16) 0.0511(18) 0.0410(16) 0.0086(14) 0.0145(13) 0.0110(14) C16 0.051(2) 0.063(2) 0.0519(19) 0.0019(16) 0.0157(16) 0.0014(17) C17 0.067(3) 0.120(4) 0.073(3) 0.016(3) -0.011(2) 0.006(3) C18 0.064(2) 0.085(3) 0.059(2) 0.022(2) 0.0147(18) 0.034(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 O1 C8 1.427(3) . ? O1 H1 0.80(3) . ? O2 C9 1.420(4) . ? O2 H2 0.82(4) . ? N1 C10 1.450(4) . ? N1 C1 1.457(3) . ? N1 C11 1.465(3) . ? C1 C2 1.503(4) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.383(4) . ? C2 C7 1.408(4) . ? C3 C4 1.371(4) . ? C3 H3 0.9300 . ? C4 C5 1.362(4) . ? C4 H4 0.9300 . ? C5 C6 1.374(4) . ? C5 H5 0.9300 . ? C6 C7 1.388(4) . ? C6 H6 0.9300 . ? C7 C8 1.522(4) . ? C8 C15 1.525(4) . ? C8 C9 1.528(4) . ? C9 C10 1.512(4) . ? C9 H9 0.9800 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.509(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.517(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.486(5) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C18 1.531(4) . ? C15 C16 1.532(4) . ? C15 H15 0.9800 . ? C16 C17 1.510(5) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.512(5) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9700 . ? C18 H18B 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 C8 O1 H1 110(3) . . ? C9 O2 H2 106(3) . . ? C10 N1 C1 112.3(2) . . ? C10 N1 C11 112.0(2) . . ? C1 N1 C11 113.3(2) . . ? N1 C1 C2 114.8(2) . . ? N1 C1 H1A 108.6 . . ? C2 C1 H1A 108.6 . . ? N1 C1 H1B 108.6 . . ? C2 C1 H1B 108.6 . . ? H1A C1 H1B 107.5 . . ? C3 C2 C7 118.4(3) . . ? C3 C2 C1 116.5(2) . . ? C7 C2 C1 125.0(3) . . ? C4 C3 C2 122.4(3) . . ? C4 C3 H3 118.8 . . ? C2 C3 H3 118.8 . . ? C5 C4 C3 119.2(3) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C4 C5 C6 120.0(3) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C5 C6 C7 122.0(3) . . ? C5 C6 H6 119.0 . . ? C7 C6 H6 119.0 . . ? C6 C7 C2 118.0(3) . . ? C6 C7 C8 118.9(2) . . ? C2 C7 C8 123.0(2) . . ? O1 C8 C7 110.4(2) . . ? O1 C8 C15 105.6(2) . . ? C7 C8 C15 108.5(2) . . ? O1 C8 C9 106.0(2) . . ? C7 C8 C9 114.1(2) . . ? C15 C8 C9 111.9(2) . . ? O2 C9 C10 108.8(2) . . ? O2 C9 C8 109.5(2) . . ? C10 C9 C8 118.4(2) . . ? O2 C9 H9 106.5 . . ? C10 C9 H9 106.5 . . ? C8 C9 H9 106.5 . . ? N1 C10 C9 110.6(2) . . ? N1 C10 H10A 109.5 . . ? C9 C10 H10A 109.5 . . ? N1 C10 H10B 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? N1 C11 C12 117.1(2) . . ? N1 C11 H11A 108.0 . . ? C12 C11 H11A 108.0 . . ? N1 C11 H11B 108.0 . . ? C12 C11 H11B 108.0 . . ? H11A C11 H11B 107.3 . . ? C11 C12 C13 111.8(3) . . ? C11 C12 H12A 109.2 . . ? C13 C12 H12A 109.2 . . ? C11 C12 H12B 109.2 . . ? C13 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? C14 C13 C12 113.7(3) . . ? C14 C13 H13A 108.8 . . ? C12 C13 H13A 108.8 . . ? C14 C13 H13B 108.8 . . ? C12 C13 H13B 108.8 . . ? H13A C13 H13B 107.7 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C8 C15 C18 120.4(2) . . ? C8 C15 C16 118.3(2) . . ? C18 C15 C16 87.9(2) . . ? C8 C15 H15 109.5 . . ? C18 C15 H15 109.5 . . ? C16 C15 H15 109.5 . . ? C17 C16 C15 88.4(3) . . ? C17 C16 H16A 113.9 . . ? C15 C16 H16A 113.9 . . ? C17 C16 H16B 113.9 . . ? C15 C16 H16B 113.9 . . ? H16A C16 H16B 111.1 . . ? C16 C17 C18 89.3(3) . . ? C16 C17 H17A 113.8 . . ? C18 C17 H17A 113.8 . . ? C16 C17 H17B 113.8 . . ? C18 C17 H17B 113.8 . . ? H17A C17 H17B 111.0 . . ? C17 C18 C15 88.4(3) . . ? C17 C18 H18A 113.9 . . ? C15 C18 H18A 113.9 . . ? C17 C18 H18B 113.9 . . ? C15 C18 H18B 113.9 . . ? H18A C18 H18B 111.1 . . ? 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 C10 N1 C1 C2 83.1(3) . . . . ? C11 N1 C1 C2 -148.8(2) . . . . ? N1 C1 C2 C3 126.6(3) . . . . ? N1 C1 C2 C7 -55.2(4) . . . . ? C7 C2 C3 C4 -0.9(4) . . . . ? C1 C2 C3 C4 177.5(3) . . . . ? C2 C3 C4 C5 1.4(5) . . . . ? C3 C4 C5 C6 -0.5(5) . . . . ? C4 C5 C6 C7 -1.0(5) . . . . ? C5 C6 C7 C2 1.5(4) . . . . ? C5 C6 C7 C8 -175.0(3) . . . . ? C3 C2 C7 C6 -0.6(4) . . . . ? C1 C2 C7 C6 -178.8(2) . . . . ? C3 C2 C7 C8 175.8(2) . . . . ? C1 C2 C7 C8 -2.5(4) . . . . ? C6 C7 C8 O1 -14.0(3) . . . . ? C2 C7 C8 O1 169.7(2) . . . . ? C6 C7 C8 C15 101.2(3) . . . . ? C2 C7 C8 C15 -75.1(3) . . . . ? C6 C7 C8 C9 -133.3(3) . . . . ? C2 C7 C8 C9 50.4(3) . . . . ? O1 C8 C9 O2 -66.9(3) . . . . ? C7 C8 C9 O2 54.8(3) . . . . ? C15 C8 C9 O2 178.5(2) . . . . ? O1 C8 C9 C10 167.6(2) . . . . ? C7 C8 C9 C10 -70.7(3) . . . . ? C15 C8 C9 C10 53.0(3) . . . . ? C1 N1 C10 C9 -77.5(3) . . . . ? C11 N1 C10 C9 153.7(2) . . . . ? O2 C9 C10 N1 -53.3(3) . . . . ? C8 C9 C10 N1 72.6(3) . . . . ? C10 N1 C11 C12 60.9(3) . . . . ? C1 N1 C11 C12 -67.4(3) . . . . ? N1 C11 C12 C13 176.0(3) . . . . ? C11 C12 C13 C14 -169.4(3) . . . . ? O1 C8 C15 C18 -60.5(3) . . . . ? C7 C8 C15 C18 -178.8(3) . . . . ? C9 C8 C15 C18 54.4(3) . . . . ? O1 C8 C15 C16 45.0(3) . . . . ? C7 C8 C15 C16 -73.4(3) . . . . ? C9 C8 C15 C16 159.8(2) . . . . ? C8 C15 C16 C17 -142.0(3) . . . . ? C18 C15 C16 C17 -18.3(3) . . . . ? C15 C16 C17 C18 18.6(3) . . . . ? C16 C17 C18 C15 -18.6(3) . . . . ? C8 C15 C18 C17 140.2(3) . . . . ? C16 C15 C18 C17 18.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.200 _refine_diff_density_min -0.185 _refine_diff_density_rms 0.044