# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 1999 # CCDC Number: 207/367 data_global _publ_contact_author 'Andrei S.Batsanov' _publ_contact_author_email a.s.batsanov@durham.ac.uk loop_ _publ_author_name 'Tavasli, Mustafa' 'O'Hagan, David' 'Batsanov, Andrei S.' 'Foxon, Graham R.' 'Halliwell, Robert F.' 'Howard, Judith A. K.' _journal_name_full 'Journal of the Chemical Society, Perkin Transactions 1' _journal_volume '?' _journal_page_first '?' _journal_page_last '?' _journal_year '1999' _ccdc_journal_depnumber '?' _publ_section_title ; The synthesis, conformation and antimuscarinic properties of ketone analogues of tropane esters ; #====================================================================== data_5.HCl _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-(tropan-3-yl)-1-para-methoxyphenyl-1-ethanone hydrochloride ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H24 N O2 1+,Cl 1-' _chemical_formula_sum 'C17 H24 Cl N O2' _chemical_formula_weight 309.82 _ccdc_compound_id '5.HCl' _ccdc_biological_activity 'antimuscarinic' _ccdc_polymorph '?' _ccdc_disorder ; none ; _ccdc_comments 'synthetic analogue of natural tropate esters' 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.341(1) _cell_length_b 11.558(1) _cell_length_c 21.415(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1569.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 685 _cell_measurement_theta_min 12 _cell_measurement_theta_max 22 _exptl_crystal_description block _exptl_crystal_colour amber _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.248 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9293 _exptl_absorpt_correction_T_max 0.9521 _exptl_absorpt_process_details ? _exptl_special_details ; Four sets of \w scans (each scan covering 0.3\% in \w, exposure time 30 s), each set having different \f and/or 2\q angles, nominally covered over a hemisphere of reciprocal space. The first 50 scans were repeated at the end of data collection, revealing no significant decay of intensities. Crystal to detector distance 4.51 cm. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 10962 _diffrn_reflns_av_R_equivalents 0.0670 _diffrn_reflns_av_sigmaI/netI 0.0491 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3571 _reflns_number_gt 3099 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0399P)^2^+0.2389P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _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 -0.05(6) _refine_ls_number_reflns 3571 _refine_ls_number_parameters 286 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0481 _refine_ls_R_factor_gt 0.0370 _refine_ls_wR_factor_ref 0.0855 _refine_ls_wR_factor_gt 0.0806 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl Cl 1.31301(8) 0.68637(4) 0.35969(2) 0.02633(12) Uani 1 1 d . . . O1 O 0.6676(2) 0.69786(12) 0.13370(7) 0.0299(3) Uani 1 1 d . . . O2 O -0.1360(2) 0.48215(12) 0.00267(7) 0.0272(3) Uani 1 1 d . . . N N 1.0065(3) 0.48554(14) 0.34309(7) 0.0206(3) Uani 1 1 d . . . H1N H 1.119(4) 0.549(2) 0.3405(10) 0.029(6) Uiso 1 1 d . . . C1 C 0.7921(3) 0.54022(17) 0.33029(9) 0.0218(4) Uani 1 1 d . . . H1 H 0.745(3) 0.5880(17) 0.3654(10) 0.015(5) Uiso 1 1 d . . . C2 C 0.8168(4) 0.61657(16) 0.27231(9) 0.0224(4) Uani 1 1 d . . . H21 H 0.922(4) 0.678(2) 0.2851(10) 0.022(5) Uiso 1 1 d . . . H22 H 0.681(4) 0.655(2) 0.2656(10) 0.027(6) Uiso 1 1 d . . . C3 C 0.8986(3) 0.55303(18) 0.21326(9) 0.0212(4) Uani 1 1 d . . . H3 H 0.960(4) 0.6091(19) 0.1890(10) 0.019(5) Uiso 1 1 d . . . C4 C 1.0648(3) 0.46057(18) 0.23110(9) 0.0230(4) Uani 1 1 d . . . H41 H 1.078(4) 0.401(2) 0.1955(13) 0.039(7) Uiso 1 1 d . . . H42 H 1.199(4) 0.500(2) 0.2352(10) 0.025(6) Uiso 1 1 d . . . C5 C 1.0183(3) 0.39547(17) 0.29171(9) 0.0204(4) Uani 1 1 d . . . H5 H 1.135(4) 0.3451(18) 0.3013(10) 0.018(5) Uiso 1 1 d . . . C6 C 0.7986(4) 0.33888(16) 0.29500(9) 0.0228(4) Uani 1 1 d . . . H61 H 0.807(4) 0.269(2) 0.3237(11) 0.029(6) Uiso 1 1 d . . . H62 H 0.748(4) 0.3096(19) 0.2532(11) 0.030(6) Uiso 1 1 d . . . C7 C 0.6510(3) 0.43324(18) 0.32170(9) 0.0231(4) Uani 1 1 d . . . H71 H 0.587(4) 0.413(2) 0.3612(13) 0.040(7) Uiso 1 1 d . . . H72 H 0.529(4) 0.451(2) 0.2945(12) 0.035(6) Uiso 1 1 d . . . C8 C 1.0308(4) 0.4360(2) 0.40698(10) 0.0253(4) Uani 1 1 d . . . H81 H 1.149(4) 0.382(2) 0.4063(11) 0.030(6) Uiso 1 1 d . . . H82 H 0.918(5) 0.404(2) 0.4195(13) 0.046(8) Uiso 1 1 d . . . H83 H 1.076(4) 0.500(2) 0.4351(11) 0.031(6) Uiso 1 1 d . . . C9 C 0.7217(3) 0.50493(17) 0.17167(9) 0.0210(4) Uani 1 1 d . . . H92 H 0.783(4) 0.446(2) 0.1416(11) 0.030(6) Uiso 1 1 d . . . H92 H 0.617(4) 0.461(2) 0.1952(11) 0.026(6) Uiso 1 1 d . . . C10 C 0.6085(3) 0.59737(16) 0.13358(9) 0.0205(4) Uani 1 1 d . . . C11 C 0.4199(3) 0.56109(18) 0.09693(9) 0.0205(4) Uani 1 1 d . . . C12 C 0.2966(3) 0.64645(17) 0.06778(9) 0.0218(4) Uani 1 1 d . . . H12 H 0.343(4) 0.725(2) 0.0700(10) 0.023(6) Uiso 1 1 d . . . C13 C 0.1134(3) 0.61801(17) 0.03637(9) 0.0241(4) Uani 1 1 d . . . H13 H 0.034(4) 0.680(2) 0.0169(11) 0.030(6) Uiso 1 1 d . . . C14 C 0.0500(3) 0.50234(18) 0.03259(9) 0.0222(4) Uani 1 1 d . . . C15 C 0.1736(3) 0.41591(16) 0.05989(9) 0.0228(4) Uani 1 1 d . . . H15 H 0.119(4) 0.336(2) 0.0576(11) 0.030(6) Uiso 1 1 d . . . C16 C 0.3572(3) 0.44573(17) 0.09190(9) 0.0215(4) Uani 1 1 d . . . H16 H 0.437(3) 0.3839(18) 0.1124(10) 0.017(5) Uiso 1 1 d . . . C17 C -0.1993(4) 0.36277(19) -0.00365(10) 0.0277(4) Uani 1 1 d . . . H171 H -0.208(4) 0.323(2) 0.0374(12) 0.033(6) Uiso 1 1 d . . . H172 H -0.347(4) 0.3682(19) -0.0227(10) 0.025(6) Uiso 1 1 d . . . H173 H -0.099(4) 0.320(2) -0.0302(12) 0.035(6) Uiso 1 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 Cl 0.0280(2) 0.0238(2) 0.0271(2) -0.0023(2) -0.0068(2) -0.0012(2) O1 0.0328(8) 0.0252(7) 0.0318(8) 0.0046(6) -0.0107(7) -0.0046(6) O2 0.0246(7) 0.0302(7) 0.0268(7) 0.0002(6) -0.0058(6) 0.0004(6) N 0.0218(8) 0.0226(8) 0.0175(8) 0.0003(6) -0.0030(6) 0.0019(7) C1 0.0215(10) 0.0257(9) 0.0181(9) -0.0008(7) -0.0025(8) 0.0058(8) C2 0.0257(10) 0.0200(9) 0.0216(9) 0.0003(7) -0.0043(9) 0.0024(9) C3 0.0220(9) 0.0228(9) 0.0188(9) 0.0046(8) -0.0032(8) -0.0020(8) C4 0.0207(11) 0.0285(11) 0.0199(10) 0.0007(8) -0.0002(7) 0.0015(8) C5 0.0220(10) 0.0219(9) 0.0172(9) -0.0015(7) -0.0029(8) 0.0042(8) C6 0.0250(10) 0.0220(9) 0.0214(9) 0.0010(7) -0.0018(9) -0.0002(8) C7 0.0213(10) 0.0276(10) 0.0204(9) 0.0031(8) 0.0016(8) 0.0013(8) C8 0.0302(11) 0.0273(10) 0.0185(9) 0.0026(9) -0.0025(9) 0.0035(10) C9 0.0223(10) 0.0221(9) 0.0186(9) 0.0007(8) -0.0016(8) 0.0009(8) C10 0.0213(9) 0.0252(9) 0.0149(9) -0.0005(7) 0.0015(8) -0.0002(7) C11 0.0224(10) 0.0264(9) 0.0127(8) -0.0007(8) 0.0003(7) 0.0021(8) C12 0.0258(10) 0.0221(9) 0.0175(9) 0.0009(7) -0.0002(9) 0.0001(8) C13 0.0269(11) 0.0264(10) 0.0190(9) 0.0029(8) -0.0007(8) 0.0060(8) C14 0.0197(9) 0.0313(10) 0.0155(9) -0.0015(8) 0.0000(7) 0.0008(8) C15 0.0240(10) 0.0204(9) 0.0239(9) -0.0008(7) -0.0003(8) -0.0008(8) C16 0.0237(10) 0.0224(9) 0.0183(9) 0.0004(8) -0.0002(7) 0.0030(8) C17 0.0265(11) 0.0312(10) 0.0253(10) 0.0010(9) -0.0046(10) -0.0019(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C10 1.220(2) . ? O2 C14 1.362(2) . ? O2 C17 1.443(3) . ? N C8 1.491(3) . ? N C5 1.517(2) . ? N C1 1.524(3) . ? N H1N 1.02(3) . ? C1 C2 1.531(3) . ? C1 C7 1.537(3) . ? C1 H1 0.98(2) . ? C2 C3 1.552(3) . ? C2 H21 1.01(2) . ? C2 H22 0.98(3) . ? C3 C9 1.536(3) . ? C3 C4 1.549(3) . ? C3 H3 0.92(2) . ? C4 C5 1.529(3) . ? C4 H41 1.03(3) . ? C4 H42 0.97(3) . ? C5 C6 1.541(3) . ? C5 H5 0.96(2) . ? C6 C7 1.547(3) . ? C6 H61 1.01(2) . ? C6 H62 1.01(2) . ? C7 H71 0.97(3) . ? C7 H72 0.99(3) . ? C8 H81 0.97(3) . ? C8 H82 0.85(3) . ? C8 H83 1.00(3) . ? C9 C10 1.524(3) . ? C9 H92 1.01(2) . ? C9 H92 0.98(2) . ? C10 C11 1.491(3) . ? C11 C16 1.396(3) . ? C11 C12 1.405(3) . ? C12 C13 1.382(3) . ? C12 H12 0.95(2) . ? C13 C14 1.398(3) . ? C13 H13 0.97(2) . ? C14 C15 1.398(3) . ? C15 C16 1.394(3) . ? C15 H15 0.99(2) . ? C16 H16 0.98(2) . ? C17 H171 1.00(3) . ? C17 H172 1.02(2) . ? C17 H173 0.98(3) . ? 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 C14 O2 C17 116.65(16) . . ? C8 N C5 113.38(15) . . ? C8 N C1 114.62(16) . . ? C5 N C1 101.42(14) . . ? C8 N H1N 104.7(13) . . ? C5 N H1N 114.9(13) . . ? C1 N H1N 108.1(13) . . ? N C1 C2 107.08(16) . . ? N C1 C7 101.96(15) . . ? C2 C1 C7 115.21(16) . . ? N C1 H1 111.6(12) . . ? C2 C1 H1 109.2(11) . . ? C7 C1 H1 111.6(11) . . ? C1 C2 C3 114.97(16) . . ? C1 C2 H21 104.7(13) . . ? C3 C2 H21 109.5(12) . . ? C1 C2 H22 106.9(14) . . ? C3 C2 H22 112.9(13) . . ? H21 C2 H22 107.3(18) . . ? C9 C3 C4 112.97(17) . . ? C9 C3 C2 113.55(17) . . ? C4 C3 C2 110.67(16) . . ? C9 C3 H3 103.8(14) . . ? C4 C3 H3 109.8(14) . . ? C2 C3 H3 105.6(14) . . ? C5 C4 C3 114.70(17) . . ? C5 C4 H41 108.1(15) . . ? C3 C4 H41 109.5(14) . . ? C5 C4 H42 108.8(13) . . ? C3 C4 H42 107.3(14) . . ? H41 C4 H42 108.2(19) . . ? N C5 C4 106.72(15) . . ? N C5 C6 102.34(16) . . ? C4 C5 C6 114.96(17) . . ? N C5 H5 107.3(12) . . ? C4 C5 H5 109.3(13) . . ? C6 C5 H5 115.3(12) . . ? C5 C6 C7 105.36(15) . . ? C5 C6 H61 108.3(14) . . ? C7 C6 H61 111.6(14) . . ? C5 C6 H62 112.8(13) . . ? C7 C6 H62 111.9(13) . . ? H61 C6 H62 106.8(18) . . ? C1 C7 C6 105.00(16) . . ? C1 C7 H71 109.6(15) . . ? C6 C7 H71 114.0(15) . . ? C1 C7 H72 111.0(15) . . ? C6 C7 H72 113.7(15) . . ? H71 C7 H72 104(2) . . ? N C8 H81 108.2(15) . . ? N C8 H82 111.7(19) . . ? H81 C8 H82 112(2) . . ? N C8 H83 107.4(14) . . ? H81 C8 H83 105.4(19) . . ? H82 C8 H83 112(2) . . ? C10 C9 C3 113.61(16) . . ? C10 C9 H92 108.1(13) . . ? C3 C9 H92 109.2(13) . . ? C10 C9 H92 108.8(13) . . ? C3 C9 H92 112.6(13) . . ? H92 C9 H92 103.9(18) . . ? O1 C10 C11 121.00(18) . . ? O1 C10 C9 121.44(17) . . ? C11 C10 C9 117.55(16) . . ? C16 C11 C12 118.54(18) . . ? C16 C11 C10 122.56(17) . . ? C12 C11 C10 118.87(18) . . ? C13 C12 C11 121.13(19) . . ? C13 C12 H12 120.7(14) . . ? C11 C12 H12 118.2(14) . . ? C12 C13 C14 119.81(19) . . ? C12 C13 H13 117.9(14) . . ? C14 C13 H13 122.2(14) . . ? O2 C14 C15 124.04(19) . . ? O2 C14 C13 116.09(18) . . ? C15 C14 C13 119.85(19) . . ? C16 C15 C14 119.81(18) . . ? C16 C15 H15 123.4(15) . . ? C14 C15 H15 116.7(15) . . ? C15 C16 C11 120.82(18) . . ? C15 C16 H16 118.1(12) . . ? C11 C16 H16 121.0(12) . . ? O2 C17 H171 112.3(14) . . ? O2 C17 H172 103.5(13) . . ? H171 C17 H172 109(2) . . ? O2 C17 H173 110.6(14) . . ? H171 C17 H173 108(2) . . ? H172 C17 H173 113.0(18) . . ? 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 C8 N C1 C2 163.31(17) . . . . ? C5 N C1 C2 -74.15(17) . . . . ? C8 N C1 C7 -75.32(19) . . . . ? C5 N C1 C7 47.23(17) . . . . ? N C1 C2 C3 57.0(2) . . . . ? C7 C1 C2 C3 -55.6(2) . . . . ? C1 C2 C3 C9 91.2(2) . . . . ? C1 C2 C3 C4 -37.0(2) . . . . ? C9 C3 C4 C5 -90.7(2) . . . . ? C2 C3 C4 C5 37.9(2) . . . . ? C8 N C5 C4 -161.54(17) . . . . ? C1 N C5 C4 75.07(18) . . . . ? C8 N C5 C6 77.3(2) . . . . ? C1 N C5 C6 -46.04(17) . . . . ? C3 C4 C5 N -59.0(2) . . . . ? C3 C4 C5 C6 53.7(2) . . . . ? N C5 C6 C7 27.11(18) . . . . ? C4 C5 C6 C7 -88.1(2) . . . . ? N C1 C7 C6 -29.87(18) . . . . ? C2 C1 C7 C6 85.7(2) . . . . ? C5 C6 C7 C1 1.8(2) . . . . ? C4 C3 C9 C10 -157.61(16) . . . . ? C2 C3 C9 C10 75.3(2) . . . . ? C3 C9 C10 O1 5.2(3) . . . . ? C3 C9 C10 C11 -173.72(16) . . . . ? O1 C10 C11 C16 175.05(19) . . . . ? C9 C10 C11 C16 -6.1(3) . . . . ? O1 C10 C11 C12 -6.9(3) . . . . ? C9 C10 C11 C12 172.00(17) . . . . ? C10 C11 C12 C13 -176.15(17) . . . . ? C17 O2 C14 C15 -3.7(3) . . . . ? C17 O2 C14 C13 177.70(18) . . . . ? C12 C13 C14 O2 177.83(17) . . . . ? O2 C14 C15 C16 -177.19(17) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N H1N Cl 1.02(3) 2.05(3) 3.0481(18) 164.2(18) . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.293 _refine_diff_density_min -0.181 _refine_diff_density_rms 0.048 #============================================END