# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 2001 # CCDC Number: 182/1891 data_eugkt10ax98 #------------------------------------------------------------------------------ _audit_creation_date '1999-09-10' _audit_creation_method 'by teXsan v1.8' _audit_update_record ; ? ; #------------------------------------------------------------------------------ _publ_requested_journal ' Chemical Communications' _publ_contact_author_name ' Prof. John R. Scheffer' _publ_contact_author_address ; Department of Chemistry University of British Columbia Vancouver, B.C. V6T 1Z1 Canada ; _publ_contact_author_phone ' (604) 822-3496 ' _publ_contact_author_fax ' (604) 822-2847 ' _publ_contact_author_email ' scheffer@chem.ubc.ca ' _publ_requested_category ' FO' _publ_requested_coeditor_name 'Prof. James D. White' loop_ _publ_author_name ; 'John R. Scheffer ' ; _publ_author_address ; Department of Chemistry University of British Columbia Vancouver, B.C. V6T 1Z1 Canada ; _publ_section_title ; 1,2,3,4-Tetrahydro-9-oxo-4a,9a-butano-9H-fluorene-6- carboxylic acid methyl ester ; _publ_section_abstract ; The case of a ketone whose photochemistry in solution is markedly different from that observed in the crystalline state is reported. ; _publ_section_comment ; ? ; _publ_section_references ; Molecular Structure Corporation. (1992-1997). teXsan. Single Crystal Structure Analysis Software. Version 1.7. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. North, A.C.T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359. Zachariasen, W. H. (1967). Acta Cryst. 23, 558-564. Altomare, A., Burla, M.C., Cammalli, G., Cascarano, M., Giacovazzo, C., Guagliardi, A., Moliterni, A.G.G., Polidori, G., Spagna, A. (1998). SIR97: a new tool for crystal structure determination and refinement. Submitted. ; #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan (MSC, 1992-1997)' _computing_structure_solution ; SIR97 (Altomare, et. al. 1998) ; _computing_structure_refinement 'teXsan (MSC, 1992-1997)' _computing_publication_material 'teXsan (MSC, 1992-1997)' #------------------------------------------------------------------------------ _cell_length_a 11.209(1) _cell_length_b 10.149(1) _cell_length_c 7.5641(8) _cell_angle_alpha 90 _cell_angle_beta 70.368(9) _cell_angle_gamma 90 _cell_volume 810.5(2) _cell_formula_units_Z 2 _cell_measurement_temperature 294.2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 37.6 _cell_measurement_theta_max 42.6 #------------------------------------------------------------------------------ _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21 ' _symmetry_Int_Tables_number 4 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x,1/2+y, -z' #------------------------------------------------------------------------------ _exptl_crystal_description 'prism' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.25 _exptl_crystal_density_diffrn 1.223 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 298.38 _chemical_formula_analytical ? _chemical_formula_sum 'C19 H22 O3 ' _chemical_formula_moiety 'C19 H22 O3 ' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 320.00 _exptl_absorpt_coefficient_mu 0.651 _exptl_absorpt_correction_type ; \y scans (North,Phillips & Matthews, 1968) ; _exptl_absorpt_correction_T_max 0.994 _exptl_absorpt_correction_T_min 0.781 _exptl_special_details ; The scan width was (1.10+0.20tan\q)\% with an \w scan speed of 32\% per minute (up to 10 scans to achieve I/\s(I) > 40). 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 294.2 _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device_type 'Rigaku AFC6S' _diffrn_measurement_method '\w - 2\q' _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_decay_% 1.74 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? ? ? ? ? ? ? _diffrn_reflns_number 1884 _reflns_number_total 1805 _reflns_number_gt 1465 _reflns_threshold_expression I>3.00\s(I) _diffrn_reflns_av_R_equivalents 0.04671 _diffrn_reflns_av_sigmaI/netI 0.050 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 4.19 _diffrn_reflns_theta_max 77.70 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 -0.04548 _diffrn_orient_matrix_UB_12 -0.05270 _diffrn_orient_matrix_UB_13 -0.06928 _diffrn_orient_matrix_UB_21 0.08300 _diffrn_orient_matrix_UB_22 -0.02510 _diffrn_orient_matrix_UB_23 -0.09540 _diffrn_orient_matrix_UB_31 0.00393 _diffrn_orient_matrix_UB_32 -0.07938 _diffrn_orient_matrix_UB_33 0.07616 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 38 0.017 0.009 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H 0 44 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; O 0 6 0.047 0.032 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_refinement_flags _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom O(1) 0.8247(3) 0.5166 -0.0463(3) 0.084(1) 1.000 . Uani d ? O(2) 0.5890(3) 0.7932(4) 0.9118(3) 0.0724(9) 1.000 . Uani d ? O(3) 0.5860(2) 0.9581(4) 0.7225(3) 0.0641(8) 1.000 . Uani d ? C(1) 1.0127(3) 0.4511(5) 0.1703(5) 0.066(1) 1.000 . Uani d ? C(2) 1.0745(3) 0.3926(6) 0.3003(6) 0.083(1) 1.000 . Uani d ? C(3) 0.9944(4) 0.4197(6) 0.5040(7) 0.079(1) 1.000 . Uani d ? C(4) 0.8644(3) 0.3634(5) 0.5466(5) 0.059(1) 1.000 . Uani d ? C(5) 0.7947(3) 0.4106(4) 0.4169(4) 0.0431(8) 1.000 . Uani d ? C(6) 0.6699(3) 0.3325(4) 0.4554(6) 0.061(1) 1.000 . Uani d ? C(7) 0.6873(4) 0.1948(5) 0.3704(7) 0.079(1) 1.000 . Uani d ? C(8) 0.7501(5) 0.2025(5) 0.1623(8) 0.089(2) 1.000 . Uani d ? C(9) 0.8795(4) 0.2671(5) 0.1123(5) 0.071(1) 1.000 . Uani d ? C(10) 0.8764(3) 0.4023(5) 0.2023(4) 0.0497(9) 1.000 . Uani d ? C(11) 0.8194(3) 0.5096(5) 0.1159(5) 0.054(1) 1.000 . Uani d ? C(12) 0.7633(3) 0.6077(4) 0.2647(4) 0.0439(8) 1.000 . Uani d ? C(13) 0.7224(3) 0.7340(5) 0.2466(4) 0.051(1) 1.000 . Uani d ? C(14) 0.6734(3) 0.8092(4) 0.4072(4) 0.0466(9) 1.000 . Uani d ? C(15) 0.6653(3) 0.7569(4) 0.5808(4) 0.0405(8) 1.000 . Uani d ? C(16) 0.7072(3) 0.6301(4) 0.5976(4) 0.0419(8) 1.000 . Uani d ? C(17) 0.7571(3) 0.5554(4) 0.4367(4) 0.0402(8) 1.000 . Uani d ? C(18) 0.6098(3) 0.8345(4) 0.7574(5) 0.0461(9) 1.000 . Uani d ? C(19) 0.5322(4) 1.0432(5) 0.8817(6) 0.079(1) 1.000 . Uani d ? H(1) 0.8140 0.3878 0.6755 0.071 1.000 . Uiso c ? H(2) 0.8718 0.2673 0.5367 0.071 1.000 . Uiso c ? H(3) 0.9880 0.5151 0.5253 0.094 1.000 . Uiso c ? H(4) 1.0349 0.3792 0.5870 0.094 1.000 . Uiso c ? H(5) 1.1585 0.4319 0.2742 0.100 1.000 . Uiso c ? H(6) 1.0831 0.2972 0.2800 0.100 1.000 . Uiso c ? H(7) 1.0649 0.4292 0.0412 0.080 1.000 . Uiso c ? H(8) 1.0101 0.5470 0.1866 0.080 1.000 . Uiso c ? H(9) 0.9349 0.2093 0.1540 0.085 1.000 . Uiso c ? H(10) 0.9142 0.2773 -0.0244 0.085 1.000 . Uiso c ? H(11) 0.7601 0.1133 0.1100 0.106 1.000 . Uiso c ? H(12) 0.6969 0.2545 0.1088 0.106 1.000 . Uiso c ? H(13) 0.5838 0.1424 0.4031 0.089 1.000 . Uiso c ? H(14) 0.7241 0.1382 0.4417 0.089 1.000 . Uiso c ? H(15) 0.6146 0.3824 0.4033 0.073 1.000 . Uiso c ? H(16) 0.6293 0.3242 0.5915 0.073 1.000 . Uiso c ? H(17) 0.7279 0.7692 0.1234 0.061 1.000 . Uiso c ? H(18) 0.6444 0.8993 0.3987 0.056 1.000 . Uiso c ? H(19) 0.7014 0.5944 0.7206 0.050 1.000 . Uiso c ? H(20) 0.5012 1.1241 0.8411 0.094 1.000 . Uiso c ? H(21) 0.4617 0.9981 0.9754 0.094 1.000 . Uiso c ? H(22) 0.5972 1.0655 0.9369 0.094 1.000 . Uiso c ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.128(2) 0.085(2) 0.046(1) 0.033(2) -0.040(1) -0.014(1) O(2) 0.103(2) 0.060(2) 0.047(1) 0.013(2) -0.016(1) -0.001(1) O(3) 0.089(2) 0.047(2) 0.061(1) 0.020(1) -0.031(1) -0.013(1) C(1) 0.052(2) 0.070(3) 0.069(2) 0.011(2) -0.009(2) 0.004(2) C(2) 0.053(2) 0.097(4) 0.102(3) 0.009(2) -0.029(2) 0.009(3) C(3) 0.076(2) 0.088(3) 0.092(3) 0.014(3) -0.054(2) 0.000(3) C(4) 0.077(2) 0.052(2) 0.053(2) 0.018(2) -0.028(2) 0.000(2) C(5) 0.049(2) 0.037(2) 0.043(2) 0.004(1) -0.015(1) 0.000(1) C(6) 0.059(2) 0.043(2) 0.078(3) -0.002(2) -0.020(2) -0.001(2) C(7) 0.082(3) 0.043(2) 0.114(4) -0.005(2) -0.034(3) -0.004(2) C(8) 0.106(4) 0.054(3) 0.125(4) 0.014(3) -0.065(3) -0.035(3) C(9) 0.094(3) 0.057(2) 0.065(2) 0.020(2) -0.032(2) -0.020(2) C(10) 0.054(2) 0.051(2) 0.046(2) 0.010(2) -0.019(1) -0.006(2) C(11) 0.065(2) 0.056(2) 0.043(2) 0.009(2) -0.021(2) -0.008(2) C(12) 0.050(2) 0.044(2) 0.041(2) 0.002(2) -0.019(1) -0.002(2) C(13) 0.066(2) 0.048(2) 0.043(2) 0.002(2) -0.025(2) 0.008(2) C(14) 0.056(2) 0.037(2) 0.051(2) 0.003(1) -0.024(2) 0.003(1) C(15) 0.041(1) 0.039(2) 0.043(2) -0.003(1) -0.016(1) -0.002(1) C(16) 0.048(2) 0.042(2) 0.039(1) 0.001(1) -0.019(1) 0.001(1) C(17) 0.041(1) 0.038(2) 0.045(2) -0.002(1) -0.018(1) 0.003(1) C(18) 0.045(2) 0.043(2) 0.052(2) 0.003(1) -0.019(1) -0.006(2) C(19) 0.104(3) 0.067(3) 0.074(3) 0.028(2) -0.042(3) -0.030(2) #------------------------------------------------------------------------------ _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00000|Fo|^2^]' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method 'Zachariasen (1967)' _refine_ls_extinction_coef 0.000041(1) _refine_ls_extinction_expression 'equ(3) Acta Cryst.(1968) A24, p213.' _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1465 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.0623 _refine_ls_R_factor_gt 0.0407 _refine_ls_wR_factor_all 0.0464 _refine_ls_wR_factor_ref 0.0444 _refine_ls_goodness_of_fit_all 2.554 _refine_ls_goodness_of_fit_ref 2.756 _refine_ls_shift/su_max 0.0000 _refine_ls_shift/su_mean 0.0000 _refine_diff_density_min -0.13 _refine_diff_density_max 0.16 #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O(1) C(11) 1.210(4) . . yes O(2) C(18) 1.188(4) . . yes O(3) C(18) 1.328(4) . . yes O(3) C(19) 1.439(4) . . yes C(1) C(2) 1.502(5) . . yes C(1) C(10) 1.546(5) . . yes C(1) H(7) 0.98 . . no C(1) H(8) 0.98 . . no C(2) C(3) 1.525(6) . . yes C(2) H(5) 0.98 . . no C(2) H(6) 0.98 . . no C(3) C(4) 1.496(6) . . yes C(3) H(3) 0.98 . . no C(3) H(4) 0.98 . . no C(4) C(5) 1.522(4) . . yes C(4) H(1) 0.98 . . no C(4) H(2) 0.98 . . no C(5) C(6) 1.548(5) . . yes C(5) C(10) 1.575(4) . . yes C(5) C(17) 1.522(4) . . yes C(6) C(7) 1.522(5) . . yes C(6) H(15) 0.98 . . no C(6) H(16) 0.98 . . no C(7) C(8) 1.495(7) . . yes C(7) H(13) 1.22 . . no C(7) H(14) 0.97 . . no C(8) C(9) 1.519(6) . . yes C(8) H(11) 0.98 . . no C(8) H(12) 0.98 . . no C(9) C(10) 1.528(5) . . yes C(9) H(9) 0.98 . . no C(9) H(10) 0.98 . . no C(10) C(11) 1.516(5) . . yes C(11) C(12) 1.476(5) . . yes C(12) C(13) 1.384(4) . . yes C(12) C(17) 1.385(4) . . yes C(13) C(14) 1.382(4) . . yes C(13) H(17) 0.98 . . no C(14) C(15) 1.391(4) . . yes C(14) H(18) 0.98 . . no C(15) C(16) 1.391(4) . . yes C(15) C(18) 1.494(4) . . yes C(16) C(17) 1.382(4) . . yes C(16) H(19) 0.98 . . no C(19) H(20) 0.98 . . no C(19) H(21) 0.98 . . no C(19) H(22) 0.98 . . no #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(18) O(3) C(19) 117.2(3) . . . yes C(2) C(1) C(10) 114.8(3) . . . yes C(2) C(1) H(7) 108.1 . . . no C(2) C(1) H(8) 108.1 . . . no C(10) C(1) H(7) 108.1 . . . no C(10) C(1) H(8) 108.1 . . . no H(7) C(1) H(8) 109.4 . . . no C(1) C(2) C(3) 110.3(3) . . . yes C(1) C(2) H(5) 109.3 . . . no C(1) C(2) H(6) 109.3 . . . no C(3) C(2) H(5) 109.3 . . . no C(3) C(2) H(6) 109.3 . . . no H(5) C(2) H(6) 109.5 . . . no C(2) C(3) C(4) 110.4(4) . . . yes C(2) C(3) H(3) 109.2 . . . no C(2) C(3) H(4) 109.3 . . . no C(4) C(3) H(3) 109.2 . . . no C(4) C(3) H(4) 109.2 . . . no H(3) C(3) H(4) 109.4 . . . no C(3) C(4) C(5) 114.5(3) . . . yes C(3) C(4) H(1) 108.2 . . . no C(3) C(4) H(2) 108.2 . . . no C(5) C(4) H(1) 108.2 . . . no C(5) C(4) H(2) 108.2 . . . no H(1) C(4) H(2) 109.5 . . . no C(4) C(5) C(6) 110.2(3) . . . yes C(4) C(5) C(10) 113.6(2) . . . yes C(4) C(5) C(17) 115.2(3) . . . yes C(6) C(5) C(10) 110.0(3) . . . yes C(6) C(5) C(17) 105.8(2) . . . yes C(10) C(5) C(17) 101.5(3) . . . yes C(5) C(6) C(7) 114.3(3) . . . yes C(5) C(6) H(15) 108.2 . . . no C(5) C(6) H(16) 108.3 . . . no C(7) C(6) H(15) 108.3 . . . no C(7) C(6) H(16) 108.3 . . . no H(15) C(6) H(16) 109.5 . . . no C(6) C(7) C(8) 110.2(4) . . . yes C(6) C(7) H(13) 109.6 . . . no C(6) C(7) H(14) 109.1 . . . no C(8) C(7) H(13) 108.3 . . . no C(8) C(7) H(14) 118.6 . . . no H(13) C(7) H(14) 100.4 . . . no C(7) C(8) C(9) 110.9(3) . . . yes C(7) C(8) H(11) 109.1 . . . no C(7) C(8) H(12) 109.1 . . . no C(9) C(8) H(11) 109.1 . . . no C(9) C(8) H(12) 109.1 . . . no H(11) C(8) H(12) 109.5 . . . no C(8) C(9) C(10) 113.5(3) . . . yes C(8) C(9) H(9) 108.5 . . . no C(8) C(9) H(10) 108.4 . . . no C(10) C(9) H(9) 108.5 . . . no C(10) C(9) H(10) 108.4 . . . no H(9) C(9) H(10) 109.5 . . . no C(1) C(10) C(5) 110.2(2) . . . yes C(1) C(10) C(9) 110.1(3) . . . yes C(1) C(10) C(11) 103.9(3) . . . yes C(5) C(10) C(9) 115.2(3) . . . yes C(5) C(10) C(11) 102.9(2) . . . yes C(9) C(10) C(11) 113.8(3) . . . yes O(1) C(11) C(10) 126.5(3) . . . yes O(1) C(11) C(12) 126.6(3) . . . yes C(10) C(11) C(12) 106.8(3) . . . yes C(11) C(12) C(13) 128.3(3) . . . yes C(11) C(12) C(17) 109.4(3) . . . yes C(13) C(12) C(17) 122.3(3) . . . yes C(12) C(13) C(14) 118.1(3) . . . yes C(12) C(13) H(17) 121.0 . . . no C(14) C(13) H(17) 121.0 . . . no C(13) C(14) C(15) 120.0(3) . . . yes C(13) C(14) H(18) 120.0 . . . no C(15) C(14) H(18) 120.0 . . . no C(14) C(15) C(16) 121.5(3) . . . yes C(14) C(15) C(18) 121.3(3) . . . yes C(16) C(15) C(18) 117.3(3) . . . yes C(15) C(16) C(17) 118.4(3) . . . yes C(15) C(16) H(19) 120.8 . . . no C(17) C(16) H(19) 120.8 . . . no C(5) C(17) C(12) 110.6(3) . . . yes C(5) C(17) C(16) 129.3(3) . . . yes C(12) C(17) C(16) 119.7(3) . . . yes O(2) C(18) O(3) 122.9(3) . . . yes O(2) C(18) C(15) 125.3(3) . . . yes O(3) C(18) C(15) 111.8(3) . . . yes O(3) C(19) H(20) 109.5 . . . no O(3) C(19) H(21) 109.5 . . . no O(3) C(19) H(22) 109.5 . . . no H(20) C(19) H(21) 109.5 . . . no H(20) C(19) H(22) 109.5 . . . no H(21) C(19) H(22) 109.5 . . . no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O(1) C(4) 3.344(4) . 1_554 no O(1) C(3) 3.437(6) . 1_554 no O(1) C(16) 3.564(4) . 1_554 no O(2) C(19) 3.049(5) . 2_647 no O(2) C(13) 3.399(4) . 1_556 no O(3) C(7) 3.482(5) . 1_565 no C(2) C(18) 3.467(5) . 2_746 no #------------------------------------------------------------------------------ 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O(1) C(11) C(10) C(1) . . . . 87.8(4) no O(1) C(11) C(10) C(5) . . . . -157.2(4) no O(1) C(11) C(10) C(9) . . . . -31.9(5) no O(1) C(11) C(12) C(13) . . . . -10.1(6) no O(1) C(11) C(12) C(17) . . . . 170.5(4) no O(2) C(18) O(3) C(19) . . . . -0.2(5) no O(2) C(18) C(15) C(14) . . . . 172.8(3) no O(2) C(18) C(15) C(16) . . . . -6.6(5) no O(3) C(18) C(15) C(14) . . . . -7.4(4) no O(3) C(18) C(15) C(16) . . . . 173.2(3) no C(1) C(2) C(3) C(4) . . . . 58.5(5) no C(1) C(2) C(3) H(3) . . . . -61.6(5) no C(1) C(2) C(3) H(4) . . . . 178.7(5) no C(1) C(10) C(5) C(4) . . . . -42.7(4) no C(1) C(10) C(5) C(6) . . . . -166.7(3) no C(1) C(10) C(5) C(17) . . . . 81.5(3) no C(1) C(10) C(9) C(8) . . . . 171.1(3) no C(1) C(10) C(9) H(9) . . . . 50.5(4) no C(1) C(10) C(9) H(10) . . . . -68.3(4) no C(1) C(10) C(11) C(12) . . . . -88.7(3) no C(2) C(1) C(10) C(5) . . . . 48.6(4) no C(2) C(1) C(10) C(9) . . . . -79.6(4) no C(2) C(1) C(10) C(11) . . . . 158.2(3) no C(2) C(3) C(4) C(5) . . . . -55.4(5) no C(2) C(3) C(4) H(1) . . . . -176.2(4) no C(2) C(3) C(4) H(2) . . . . 65.3(4) no C(3) C(2) C(1) C(10) . . . . -57.2(5) no C(3) C(2) C(1) H(7) . . . . -178.0(4) no C(3) C(2) C(1) H(8) . . . . 63.6(5) no C(3) C(4) C(5) C(6) . . . . 172.2(3) no C(3) C(4) C(5) C(10) . . . . 48.3(4) no C(3) C(4) C(5) C(17) . . . . -68.2(4) no C(4) C(3) C(2) H(5) . . . . 178.7(4) no C(4) C(3) C(2) H(6) . . . . -61.6(4) no C(4) C(5) C(6) C(7) . . . . -77.9(4) no C(4) C(5) C(6) H(15) . . . . 161.4(3) no C(4) C(5) C(6) H(16) . . . . 42.8(4) no C(4) C(5) C(10) C(9) . . . . 82.6(4) no C(4) C(5) C(10) C(11) . . . . -153.0(3) no C(4) C(5) C(17) C(12) . . . . 145.9(3) no C(4) C(5) C(17) C(16) . . . . -42.0(5) no C(5) C(4) C(3) H(3) . . . . 64.7(5) no C(5) C(4) C(3) H(4) . . . . -175.6(4) no C(5) C(6) C(7) C(8) . . . . -58.9(5) no C(5) C(6) C(7) H(13) . . . . -178.0(3) no C(5) C(6) C(7) H(14) . . . . 73.0(5) no C(5) C(10) C(1) H(7) . . . . 169.4(4) no C(5) C(10) C(1) H(8) . . . . -72.2(4) no C(5) C(10) C(9) C(8) . . . . 45.7(4) no C(5) C(10) C(9) H(9) . . . . -74.9(4) no C(5) C(10) C(9) H(10) . . . . 166.3(3) no C(5) C(10) C(11) C(12) . . . . 26.2(3) no C(5) C(17) C(12) C(11) . . . . -6.8(3) no C(5) C(17) C(12) C(13) . . . . 173.7(3) no C(5) C(17) C(16) C(15) . . . . -171.9(3) no C(5) C(17) C(16) H(19) . . . . 8.1(5) no C(6) C(5) C(4) H(1) . . . . -67.0(4) no C(6) C(5) C(4) H(2) . . . . 51.5(4) no C(6) C(5) C(10) C(9) . . . . -41.4(4) no C(6) C(5) C(10) C(11) . . . . 83.0(3) no C(6) C(5) C(17) C(12) . . . . -92.2(3) no C(6) C(5) C(17) C(16) . . . . 79.9(4) no C(6) C(7) C(8) C(9) . . . . 60.1(5) no C(6) C(7) C(8) H(11) . . . . -179.7(4) no C(6) C(7) C(8) H(12) . . . . -60.1(5) no C(7) C(6) C(5) C(10) . . . . 48.1(4) no C(7) C(6) C(5) C(17) . . . . 157.0(3) no C(7) C(8) C(9) C(10) . . . . -54.5(5) no C(7) C(8) C(9) H(9) . . . . 66.1(5) no C(7) C(8) C(9) H(10) . . . . -175.1(4) no C(8) C(7) C(6) H(15) . . . . 61.8(5) no C(8) C(7) C(6) H(16) . . . . -179.6(3) no C(8) C(9) C(10) C(11) . . . . -72.7(4) no C(9) C(8) C(7) H(13) . . . . 179.9(3) no C(9) C(8) C(7) H(14) . . . . -66.6(5) no C(9) C(10) C(1) H(7) . . . . 41.2(4) no C(9) C(10) C(1) H(8) . . . . 159.6(3) no C(9) C(10) C(5) C(17) . . . . -153.1(3) no C(9) C(10) C(11) C(12) . . . . 151.5(3) no C(10) C(1) C(2) H(5) . . . . -177.3(4) no C(10) C(1) C(2) H(6) . . . . 62.9(4) no C(10) C(5) C(4) H(1) . . . . 169.0(3) no C(10) C(5) C(4) H(2) . . . . -72.5(4) no C(10) C(5) C(6) H(15) . . . . -72.6(4) no C(10) C(5) C(6) H(16) . . . . 168.8(3) no C(10) C(5) C(17) C(12) . . . . 22.7(3) no C(10) C(5) C(17) C(16) . . . . -165.2(3) no C(10) C(9) C(8) H(11) . . . . -174.7(4) no C(10) C(9) C(8) H(12) . . . . 65.7(5) no C(10) C(11) C(12) C(13) . . . . 166.4(3) no C(10) C(11) C(12) C(17) . . . . -13.0(4) no C(11) C(10) C(1) H(7) . . . . -81.0(4) no C(11) C(10) C(1) H(8) . . . . 37.5(4) no C(11) C(10) C(5) C(17) . . . . -28.8(3) no C(11) C(10) C(9) H(9) . . . . 166.6(3) no C(11) C(10) C(9) H(10) . . . . 47.8(5) no C(11) C(12) C(13) C(14) . . . . -179.6(3) no C(11) C(12) C(13) H(17) . . . . 0.4(6) no C(11) C(12) C(17) C(16) . . . . -179.8(3) no C(12) C(13) C(14) C(15) . . . . -0.6(5) no C(12) C(13) C(14) H(18) . . . . 179.4(3) no C(12) C(17) C(16) C(15) . . . . -0.4(4) no C(12) C(17) C(16) H(19) . . . . 179.6(3) no C(13) C(12) C(17) C(16) . . . . 0.7(4) no C(13) C(14) C(15) C(16) . . . . 0.9(5) no C(13) C(14) C(15) C(18) . . . . -178.4(3) no C(14) C(13) C(12) C(17) . . . . -0.2(5) no C(14) C(15) C(16) C(17) . . . . -0.4(4) no C(14) C(15) C(16) H(19) . . . . 179.6(3) no C(15) C(14) C(13) H(17) . . . . 179.4(3) no C(15) C(18) O(3) C(19) . . . . -180.0(3) no C(16) C(15) C(14) H(18) . . . . -179.1(3) no C(17) C(5) C(4) H(1) . . . . 52.6(5) no C(17) C(5) C(4) H(2) . . . . 171.1(3) no C(17) C(5) C(6) H(15) . . . . 36.2(4) no C(17) C(5) C(6) H(16) . . . . -82.3(4) no C(17) C(12) C(13) H(17) . . . . 179.8(3) no C(17) C(16) C(15) C(18) . . . . 179.0(3) no C(18) O(3) C(19) H(20) . . . . -167.1(4) no C(18) O(3) C(19) H(21) . . . . -47.1(5) no C(18) O(3) C(19) H(22) . . . . 72.9(5) no C(18) C(15) C(14) H(18) . . . . 1.6(5) no C(18) C(15) C(16) H(19) . . . . -1.0(4) no H(1) C(4) C(3) H(3) . . . . -56.0(5) no H(1) C(4) C(3) H(4) . . . . 63.7(5) no H(2) C(4) C(3) H(3) . . . . -174.5(3) no H(2) C(4) C(3) H(4) . . . . -54.8(5) no H(3) C(3) C(2) H(5) . . . . 58.5(5) no H(3) C(3) C(2) H(6) . . . . 178.3(3) no H(4) C(3) C(2) H(5) . . . . -61.2(6) no H(4) C(3) C(2) H(6) . . . . 58.6(6) no H(5) C(2) C(1) H(7) . . . . 61.9(5) no H(5) C(2) C(1) H(8) . . . . -56.5(5) no H(6) C(2) C(1) H(7) . . . . -57.9(5) no H(6) C(2) C(1) H(8) . . . . -176.3(3) no H(9) C(9) C(8) H(11) . . . . -54.1(6) no H(9) C(9) C(8) H(12) . . . . -173.7(4) no H(10) C(9) C(8) H(11) . . . . 64.7(5) no H(10) C(9) C(8) H(12) . . . . -54.9(5) no H(11) C(8) C(7) H(13) . . . . -59.8(5) no H(11) C(8) C(7) H(14) . . . . 53.6(6) no H(12) C(8) C(7) H(13) . . . . 59.7(5) no H(12) C(8) C(7) H(14) . . . . 173.2(5) no H(13) C(7) C(6) H(15) . . . . -57.3(5) no H(13) C(7) C(6) H(16) . . . . 61.3(5) no H(14) C(7) C(6) H(15) . . . . -166.3(4) no H(14) C(7) C(6) H(16) . . . . -47.7(5) no H(17) C(13) C(14) H(18) . . . . -0.6(6) no #------------------------------------------------------------------------------ data__phenyl_ester_cis #------------------------------------------------------------------------------ _audit_creation_date '19100-01-31' _audit_creation_method 'by teXsan v1.8' _audit_update_record ; ? ; #------------------------------------------------------------------------------ _publ_requested_journal ' Chemical Communications' _publ_contact_author_name ' Prof. John R. Scheffer' _publ_contact_author_address ; Department of Chemistry University of British Columbia Vancouver, B.C. V6T 1Z1 Canada ; _publ_contact_author_phone ' (604) 822-3496 ' _publ_contact_author_fax ' (604) 822-2847 ' _publ_contact_author_email ' scheffer@chem.ubc.ca ' _publ_requested_category ' FO' _publ_requested_coeditor_name 'Prof. James D. White' loop_ _publ_author_name ; 'John R. Scheffer ' ; _publ_author_address ; Department of Chemistry University of British Columbia Vancouver, B.C. V6T 1Z1 Canada ; _publ_section_title ; 4-[(cis-octahydro-4a-(2H)-naphthalenylcarbonyl)]benzoic acid methyl ester ; _publ_section_title_footnote ' ? ' _publ_section_abstract ; The case of a ketone whose photochemistry in solution is markedly different from that observed in the crystalline state is reported. ; _publ_section_comment ; ENTER TEXT ; _publ_section_references ; Molecular Structure Corporation. (1992-1997). teXsan. Single Crystal Structure Analysis Software. Version 1.7. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. North, A.C.T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359. Altomare, A., Cascarano, M., Giacovazzo, C., Guagliardi, A. (1993). J. Appl. Cryst., 26, 343. ; _publ_section_acknowledgements ; ENTER ACKNOWLEDGEMENTS ; _publ_section_table_legends ; ENTER TABLE LEGENDS ; _publ_section_figure_captions ; ENTER FIGURE CAPTIONS ; #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan (MSC, 1992-1997)' _computing_structure_solution ; SIR92 (Altomare, et. al. 1993) ; _computing_structure_refinement 'teXsan (MSC, 1992-1997)' _computing_publication_material 'teXsan (MSC, 1992-1997)' #------------------------------------------------------------------------------ _cell_length_a 13.881(5) _cell_length_b 6.362(2) _cell_length_c 18.179(8) _cell_angle_alpha 90 _cell_angle_beta 97.77(4) _cell_angle_gamma 90 _cell_volume 1591(1) _cell_formula_units_Z 4 _cell_measurement_temperature 294.2 _cell_measurement_reflns_used 9 _cell_measurement_theta_min 5.9 _cell_measurement_theta_max 10.0 #------------------------------------------------------------------------------ _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/a ' _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' '1/2-x,1/2+y, -z' ' -x, -y, -z' '1/2+x,1/2-y, +z' #------------------------------------------------------------------------------ _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _exptl_crystal_description 'cube' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _chemical_formula_analytical ? _exptl_crystal_density_diffrn 1.254 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 300.40 _chemical_formula_sum 'C19 H24 O3 ' _chemical_formula_moiety 'C19 H24 O3 ' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type ; \y scans (North,Phillips & Matthews, 1968) ; _exptl_absorpt_correction_T_max 0.999 _exptl_absorpt_correction_T_min 0.951 _exptl_special_details ; The scan width was (1.26+0.35tan\q)\% with an \w scan speed of 16\% per minute (up to 10 scans to achieve I/\s(I) > 40). 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 294.2 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device_type 'Rigaku AFC6S' _diffrn_measurement_method \w-2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_decay_% 0.63 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 2 -2 1 4 0 0 -4 -2 5 _diffrn_reflns_number 2611 _reflns_number_total 2503 _reflns_number_gt 834 _reflns_threshold_expression I>3.00\s(I) _diffrn_reflns_av_R_equivalents 0.02625 _diffrn_reflns_av_sigmaI/netI 0.140 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 0.04357 _diffrn_orient_matrix_UB_12 -0.06507 _diffrn_orient_matrix_UB_13 0.04220 _diffrn_orient_matrix_UB_21 -0.05605 _diffrn_orient_matrix_UB_22 -0.01053 _diffrn_orient_matrix_UB_23 0.02905 _diffrn_orient_matrix_UB_31 -0.01570 _diffrn_orient_matrix_UB_32 -0.14271 _diffrn_orient_matrix_UB_33 -0.02138 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 76 0.002 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H 0 96 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; O 0 12 0.008 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ loop_ _atom_site_label _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 0.7705(3) 0.1873(6) 0.2226(3) 0.163(2) Uani 1 d . . . O2 1.1511(5) 0.5504(8) 0.0514(3) 0.188(3) Uani 1 d . . . O3 1.0956(4) 0.8736(7) 0.0645(2) 0.1510(19) Uani 1 d . . . C1 0.8343(3) 0.6038(6) 0.3523(3) 0.0887(17) Uani 1 d . . . H1A 0.8639 0.7025 0.3205 0.106 Uiso 1 calc R . . H1B 0.8043 0.6860 0.3887 0.106 Uiso 1 calc R . . C2 0.9139(3) 0.4638(7) 0.3932(3) 0.103(2) Uani 1 d . . . H2A 0.9485 0.3917 0.3570 0.123 Uiso 1 calc R . . H2B 0.9608 0.5511 0.4247 0.123 Uiso 1 calc R . . C3 0.8704(3) 0.3014(7) 0.4410(4) 0.110(2) Uani 1 d . . . H3A 0.9218 0.2076 0.4641 0.132 Uiso 1 calc R . . H3B 0.8420 0.3729 0.4807 0.132 Uiso 1 calc R . . C4 0.7926(3) 0.1733(6) 0.3944(4) 0.106(2) Uani 1 d . . . H4A 0.7638 0.0751 0.4268 0.127 Uiso 1 calc R . . H4B 0.8230 0.0902 0.3584 0.127 Uiso 1 calc R . . C5 0.7122(3) 0.3077(7) 0.3529(4) 0.1018(19) Uani 1 d . . . H5 0.6719 0.2139 0.3188 0.122 Uiso 1 calc R . . C6 0.6460(3) 0.4039(7) 0.4036(4) 0.113(2) Uani 1 d . . . H6A 0.6177 0.2908 0.4304 0.136 Uiso 1 calc R . . H6B 0.6850 0.4923 0.4405 0.136 Uiso 1 calc R . . C7 0.5644(3) 0.5353(7) 0.3634(4) 0.119(2) Uani 1 d . . . H7A 0.5251 0.5947 0.3992 0.143 Uiso 1 calc R . . H7B 0.5223 0.4473 0.3284 0.143 Uiso 1 calc R . . C8 0.6081(3) 0.7119(7) 0.3218(4) 0.120(2) Uani 1 d . . . H8A 0.5558 0.7945 0.2939 0.143 Uiso 1 calc R . . H8B 0.6462 0.8056 0.3573 0.143 Uiso 1 calc R . . C9 0.6729(4) 0.6215(7) 0.2688(4) 0.118(2) Uani 1 d . . . H9A 0.7020 0.7384 0.2445 0.142 Uiso 1 calc R . . H9B 0.6321 0.5423 0.2302 0.142 Uiso 1 calc R . . C10 0.7551(3) 0.4767(7) 0.3043(3) 0.0938(18) Uani 1 d . . . C11 0.7977(4) 0.3652(8) 0.2415(4) 0.117(2) Uani 1 d . . . C12 0.8738(5) 0.4599(7) 0.2005(4) 0.112(2) Uani 1 d . . . C13 0.8772(5) 0.6681(8) 0.1775(4) 0.121(2) Uani 1 d . . . H13 0.8284 0.7677 0.1907 0.146 Uiso 1 calc R . . C14 0.9473(6) 0.7370(8) 0.1370(4) 0.127(2) Uani 1 d . . . H14 0.9478 0.8843 0.1213 0.153 Uiso 1 calc R . . C15 1.0176(6) 0.6002(9) 0.1179(4) 0.119(2) Uani 1 d . . . C16 1.0164(5) 0.3934(8) 0.1412(4) 0.127(2) Uani 1 d . . . H16 1.0665 0.2952 0.1293 0.152 Uiso 1 calc R . . C17 0.9450(5) 0.3258(8) 0.1810(4) 0.115(2) Uani 1 d . . . H17 0.9443 0.1780 0.1961 0.138 Uiso 1 calc R . . C18 1.0946(7) 0.6673(11) 0.0738(4) 0.145(3) Uani 1 d . . . C19 1.1707(6) 0.9536(10) 0.0231(4) 0.163(3) Uani 1 d . . . H19A 1.2349 0.9186 0.0496 0.245 Uiso 1 calc R . . H19B 1.1645 1.1066 0.0182 0.245 Uiso 1 calc R . . H19C 1.1631 0.8895 -0.0264 0.245 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 0.164(4) 0.063(2) 0.273(6) -0.057(3) 0.070(4) -0.029(2) O2 0.318(7) 0.102(4) 0.178(5) 0.018(3) 0.160(5) 0.028(4) O3 0.249(5) 0.087(3) 0.134(4) 0.016(3) 0.089(4) 0.000(3) C1 0.062(3) 0.044(2) 0.162(5) -0.013(3) 0.022(3) -0.001(2) C2 0.053(3) 0.058(3) 0.196(6) -0.001(3) 0.015(3) 0.001(3) C3 0.064(3) 0.058(3) 0.207(6) 0.007(4) 0.016(4) -0.008(3) C4 0.067(3) 0.042(2) 0.209(6) 0.003(3) 0.024(4) -0.002(3) C5 0.060(3) 0.043(2) 0.202(6) -0.013(3) 0.018(4) -0.009(2) C6 0.055(3) 0.059(3) 0.229(7) -0.001(4) 0.027(4) 0.000(3) C7 0.055(3) 0.064(3) 0.238(7) -0.009(4) 0.019(4) -0.005(3) C8 0.061(3) 0.060(3) 0.235(7) -0.007(4) 0.010(4) 0.010(3) C9 0.076(3) 0.060(3) 0.214(7) -0.009(4) 0.000(4) 0.001(3) C10 0.058(3) 0.043(2) 0.180(6) -0.018(3) 0.012(3) 0.000(2) C11 0.099(4) 0.045(3) 0.210(7) -0.017(4) 0.033(4) 0.001(3) C12 0.137(5) 0.043(3) 0.159(6) -0.015(3) 0.037(4) 0.002(3) C13 0.136(6) 0.052(3) 0.180(7) -0.006(4) 0.032(5) 0.004(3) C14 0.198(7) 0.050(3) 0.140(6) -0.003(4) 0.042(5) -0.001(4) C15 0.191(7) 0.064(4) 0.109(5) -0.005(4) 0.050(5) 0.008(4) C16 0.197(7) 0.063(4) 0.136(6) 0.010(4) 0.078(5) 0.023(4) C17 0.166(6) 0.054(3) 0.136(5) 0.003(3) 0.058(5) 0.016(4) C18 0.251(9) 0.074(5) 0.122(6) 0.008(4) 0.070(6) 0.011(5) C19 0.284(9) 0.121(5) 0.104(5) 0.034(4) 0.095(6) -0.012(6) #------------------------------------------------------------------------------ _refine_special_details ; ? ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0865P)^2^+0.5698P] 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 0.015(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2252 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2021 _refine_ls_R_factor_gt 0.0616 _refine_ls_wR_factor_ref 0.2159 _refine_ls_wR_factor_gt 0.1725 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 #------------------------------------------------------------------------------ _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 C11 1.228(5) . ? O2 C18 1.192(8) . ? O3 C18 1.324(7) . ? O3 C19 1.458(7) . ? C1 C2 1.531(6) . ? C1 C10 1.538(6) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C2 C3 1.527(6) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C3 C4 1.517(6) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C4 C5 1.522(6) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C5 C6 1.517(7) . ? C5 C10 1.560(7) . ? C5 H5 0.9800 . ? C6 C7 1.513(6) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C7 C8 1.526(6) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C8 C9 1.517(7) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C9 C10 1.538(7) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C10 C11 1.529(7) . ? C11 C12 1.499(7) . ? C12 C17 1.388(7) . ? C12 C13 1.392(7) . ? C13 C14 1.370(7) . ? C13 H13 0.9800 . ? C14 C15 1.386(8) . ? C14 H14 0.9800 . ? C15 C16 1.383(7) . ? C15 C18 1.483(9) . ? C16 C17 1.373(7) . ? C16 H16 0.9800 . ? C17 H17 0.9800 . ? C19 H19A 0.9801 . ? C19 H19B 0.9801 . ? C19 H19C 0.9801 . ? 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 C18 O3 C19 115.6(6) . . ? C2 C1 C10 112.5(4) . . ? C2 C1 H1A 109.1 . . ? C10 C1 H1A 109.1 . . ? C2 C1 H1B 109.1 . . ? C10 C1 H1B 109.1 . . ? H1A C1 H1B 107.8 . . ? C3 C2 C1 110.8(4) . . ? C3 C2 H2A 109.5 . . ? C1 C2 H2A 109.5 . . ? C3 C2 H2B 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 108.1 . . ? C4 C3 C2 110.6(5) . . ? C4 C3 H3A 109.5 . . ? C2 C3 H3A 109.5 . . ? C4 C3 H3B 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? C3 C4 C5 113.2(4) . . ? C3 C4 H4A 108.9 . . ? C5 C4 H4A 108.9 . . ? C3 C4 H4B 108.9 . . ? C5 C4 H4B 108.9 . . ? H4A C4 H4B 107.8 . . ? C6 C5 C4 112.9(5) . . ? C6 C5 C10 112.0(4) . . ? C4 C5 C10 111.0(4) . . ? C6 C5 H5 106.8 . . ? C4 C5 H5 106.8 . . ? C10 C5 H5 106.8 . . ? C7 C6 C5 113.9(5) . . ? C7 C6 H6A 108.8 . . ? C5 C6 H6A 108.8 . . ? C7 C6 H6B 108.8 . . ? C5 C6 H6B 108.8 . . ? H6A C6 H6B 107.7 . . ? C6 C7 C8 108.9(4) . . ? C6 C7 H7A 109.9 . . ? C8 C7 H7A 109.9 . . ? C6 C7 H7B 109.9 . . ? C8 C7 H7B 109.9 . . ? H7A C7 H7B 108.3 . . ? C9 C8 C7 110.2(4) . . ? C9 C8 H8A 109.6 . . ? C7 C8 H8A 109.6 . . ? C9 C8 H8B 109.6 . . ? C7 C8 H8B 109.6 . . ? H8A C8 H8B 108.1 . . ? C8 C9 C10 115.5(5) . . ? C8 C9 H9A 108.4 . . ? C10 C9 H9A 108.4 . . ? C8 C9 H9B 108.4 . . ? C10 C9 H9B 108.4 . . ? H9A C9 H9B 107.5 . . ? C11 C10 C1 110.4(4) . . ? C11 C10 C9 107.8(5) . . ? C1 C10 C9 110.8(4) . . ? C11 C10 C5 108.6(4) . . ? C1 C10 C5 109.8(5) . . ? C9 C10 C5 109.4(4) . . ? O1 C11 C12 116.2(6) . . ? O1 C11 C10 120.1(6) . . ? C12 C11 C10 123.7(4) . . ? C17 C12 C13 117.0(6) . . ? C17 C12 C11 117.0(5) . . ? C13 C12 C11 125.9(5) . . ? C14 C13 C12 121.4(6) . . ? C14 C13 H13 119.3 . . ? C12 C13 H13 119.3 . . ? C13 C14 C15 120.6(5) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C16 C15 C14 118.9(6) . . ? C16 C15 C18 118.6(6) . . ? C14 C15 C18 122.5(6) . . ? C17 C16 C15 119.9(6) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C17 C12 122.2(5) . . ? C16 C17 H17 118.9 . . ? C12 C17 H17 118.9 . . ? O2 C18 O3 123.8(8) . . ? O2 C18 C15 124.1(6) . . ? O3 C18 C15 112.0(7) . . ? O3 C19 H19A 109.5 . . ? O3 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O3 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 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 C10 C1 C2 C3 -56.5(6) . . . . ? C1 C2 C3 C4 55.4(5) . . . . ? C2 C3 C4 C5 -56.0(6) . . . . ? C3 C4 C5 C6 -71.7(5) . . . . ? C3 C4 C5 C10 55.0(6) . . . . ? C4 C5 C6 C7 -179.0(4) . . . . ? C10 C5 C6 C7 54.8(5) . . . . ? C5 C6 C7 C8 -58.6(6) . . . . ? C6 C7 C8 C9 56.9(6) . . . . ? C7 C8 C9 C10 -55.8(6) . . . . ? C2 C1 C10 C11 -64.9(6) . . . . ? C2 C1 C10 C9 175.8(5) . . . . ? C2 C1 C10 C5 54.8(5) . . . . ? C8 C9 C10 C11 168.0(4) . . . . ? C8 C9 C10 C1 -71.2(5) . . . . ? C8 C9 C10 C5 50.1(6) . . . . ? C6 C5 C10 C11 -165.1(4) . . . . ? C4 C5 C10 C11 67.6(5) . . . . ? C6 C5 C10 C1 74.1(5) . . . . ? C4 C5 C10 C1 -53.1(5) . . . . ? C6 C5 C10 C9 -47.7(6) . . . . ? C4 C5 C10 C9 -175.0(5) . . . . ? C1 C10 C11 O1 141.9(6) . . . . ? C9 C10 C11 O1 -97.0(7) . . . . ? C5 C10 C11 O1 21.5(7) . . . . ? C1 C10 C11 C12 -37.4(7) . . . . ? C9 C10 C11 C12 83.8(6) . . . . ? C5 C10 C11 C12 -157.8(5) . . . . ? O1 C11 C12 C17 -37.2(9) . . . . ? C10 C11 C12 C17 142.1(6) . . . . ? O1 C11 C12 C13 140.0(7) . . . . ? C10 C11 C12 C13 -40.7(10) . . . . ? C17 C12 C13 C14 0.5(10) . . . . ? C11 C12 C13 C14 -176.7(6) . . . . ? C12 C13 C14 C15 -0.3(11) . . . . ? C13 C14 C15 C16 -0.7(10) . . . . ? C13 C14 C15 C18 179.7(7) . . . . ? C14 C15 C16 C17 1.6(10) . . . . ? C18 C15 C16 C17 -178.8(7) . . . . ? C15 C16 C17 C12 -1.4(10) . . . . ? C13 C12 C17 C16 0.3(10) . . . . ? C11 C12 C17 C16 177.8(6) . . . . ? C19 O3 C18 O2 1.1(12) . . . . ? C19 O3 C18 C15 178.6(6) . . . . ? C16 C15 C18 O2 6.7(12) . . . . ? C14 C15 C18 O2 -173.7(8) . . . . ? C16 C15 C18 O3 -170.9(7) . . . . ? C14 C15 C18 O3 8.7(10) . . . . ? _diffrn_measured_fraction_theta_max 0.565 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.565 _refine_diff_density_max 0.137 _refine_diff_density_min -0.149 _refine_diff_density_rms 0.037 #------------------------------------------------------------------------------ data_kt14 #------------------------------------------------------------------------------ _audit_creation_date '1999-09-10' _audit_creation_method 'by teXsan v1.8' _audit_update_record ; ? ; #------------------------------------------------------------------------------ _publ_requested_journal ' Chemical Communications' _publ_contact_author_name ' Prof. John R. Scheffer' _publ_contact_author_address ; Department of Chemistry University of British Columbia Vancouver, B.C. V6T 1Z1 Canada ; _publ_contact_author_phone ' (604) 822-3496 ' _publ_contact_author_fax ' (604) 822-2847 ' _publ_contact_author_email ' scheffer@chem.ubc.ca ' _publ_requested_category ' FO' _publ_requested_coeditor_name 'Prof. James D. White' loop_ _publ_author_name ; 'John R. Scheffer ' ; _publ_author_address ; Department of Chemistry University of British Columbia Vancouver, B.C. V6T 1Z1 Canada ; _publ_section_title ; 4-[(4aR,8S,8aR,9S)-octahydro-9-hydroxy-2H-4a,8- methanonaphthalen-9-yl]benzoic acid methyl ester ; _publ_section_abstract ; The case of a ketone whose photochemistry in solution is markedly different from that observed in the crystalline state is reported. ; _publ_section_comment ; ? ; _publ_section_references ; Molecular Structure Corporation. (1992-1997). teXsan. Single Crystal Structure Analysis Software. Version 1.7. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. North, A.C.T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359. Zachariasen, W. H. (1967). Acta Cryst. 23, 558-564. Altomare, A., Burla, M.C., Cammalli, G., Cascarano, M., Giacovazzo, C., Guagliardi, A., Moliterni, A.G.G., Polidori, G., Spagna, A. (1998). SIR97: a new tool for crystal structure determination and refinement. Submitted. ; #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan (MSC, 1992-1997)' _computing_structure_solution ; SIR97 (Altomare, et. al. 1998) ; _computing_structure_refinement 'teXsan (MSC, 1992-1997)' _computing_publication_material 'teXsan (MSC, 1992-1997)' #------------------------------------------------------------------------------ _cell_length_a 8.083(3) _cell_length_b 17.365(7) _cell_length_c 6.182(2) _cell_angle_alpha 90.99(3) _cell_angle_beta 109.53(3) _cell_angle_gamma 79.04(3) _cell_volume 801.9(5) _cell_formula_units_Z 2 _cell_measurement_temperature 294.2 _cell_measurement_reflns_used 15 _cell_measurement_theta_min 56.6 _cell_measurement_theta_max 57.3 #------------------------------------------------------------------------------ _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_Int_Tables_number 2 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x, -y, -z' #------------------------------------------------------------------------------ _exptl_crystal_description 'block' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_diffrn 1.244 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 300.40 _chemical_formula_analytical ? _chemical_formula_sum 'C19 H24 O3 ' _chemical_formula_moiety 'C19 H24 O3 ' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 324.00 _exptl_absorpt_coefficient_mu 0.659 _exptl_absorpt_correction_type ; \y scans (North,Phillips & Matthews, 1968) ; _exptl_absorpt_correction_T_max 0.984 _exptl_absorpt_correction_T_min 0.872 _exptl_special_details ; The scan width was (1.42+0.20tan\q)\% with an \w scan speed of 32\% per minute (up to 10 scans to achieve I/\s(I) > 40). 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 294.2 _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device_type 'Rigaku AFC6S' _diffrn_measurement_method \w-2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_decay_% -0.27 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? ? ? ? ? ? ? _diffrn_reflns_number 3515 _reflns_number_total 3263 _reflns_number_gt 2814 _reflns_threshold_expression I>3.00\s(I) _diffrn_reflns_av_R_equivalents 0.01664 _diffrn_reflns_av_sigmaI/netI 0.030 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 77.46 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 0.05915 _diffrn_orient_matrix_UB_12 -0.03277 _diffrn_orient_matrix_UB_13 -0.09824 _diffrn_orient_matrix_UB_21 0.03835 _diffrn_orient_matrix_UB_22 -0.04502 _diffrn_orient_matrix_UB_23 0.11600 _diffrn_orient_matrix_UB_31 -0.11379 _diffrn_orient_matrix_UB_32 -0.01868 _diffrn_orient_matrix_UB_33 -0.08014 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 38 0.017 0.009 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H 0 48 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; O 0 6 0.047 0.032 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_refinement_flags _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom O(1) 0.1746(2) 0.3040(1) 0.4029(3) 0.0553(5) 1.000 . Uani d ? O(2) 0.8690(3) 0.4201(1) 0.1251(4) 0.0779(8) 1.000 . Uani d ? O(3) 0.6485(3) 0.4481(1) -0.2102(3) 0.0650(6) 1.000 . Uani d ? C(1) 0.2584(4) 0.1417(2) 0.0082(4) 0.0506(8) 1.000 . Uani d ? C(2) 0.4564(4) 0.1133(2) 0.1432(6) 0.071(1) 1.000 . Uani d ? C(3) 0.5033(4) 0.1187(2) 0.4039(5) 0.0558(8) 1.000 . Uani d ? C(4) 0.3604(3) 0.1752(2) 0.4656(4) 0.0468(7) 1.000 . Uani d ? C(5) 0.1757(3) 0.1502(2) 0.3688(4) 0.0476(7) 1.000 . Uani d ? C(6) 0.1225(4) 0.0711(2) 0.3408(5) 0.0598(9) 1.000 . Uani d ? C(7) -0.0787(4) 0.0897(2) 0.1926(6) 0.067(1) 1.000 . Uani d ? C(8) -0.1246(4) 0.1392(2) -0.0291(5) 0.0623(9) 1.000 . Uani d ? C(9) -0.0458(4) 0.2144(2) -0.0018(4) 0.0537(8) 1.000 . Uani d ? C(10) 0.1522(3) 0.1923(1) 0.1401(4) 0.0421(6) 1.000 . Uani d ? C(11) 0.2723(3) 0.2485(1) 0.2948(4) 0.0430(6) 1.000 . Uani d ? C(12) 0.3850(3) 0.2900(1) 0.2082(4) 0.0450(7) 1.000 . Uani d ? C(13) 0.3314(3) 0.3219(2) -0.0143(4) 0.0499(7) 1.000 . Uani d ? C(14) 0.4348(4) 0.3631(2) -0.0856(4) 0.0512(7) 1.000 . Uani d ? C(15) 0.6002(3) 0.3738(1) 0.0687(4) 0.0477(7) 1.000 . Uani d ? C(16) 0.6558(4) 0.3418(2) 0.2912(4) 0.0509(7) 1.000 . Uani d ? C(17) 0.5509(4) 0.3017(2) 0.3614(4) 0.0510(7) 1.000 . Uani d ? C(18) 0.7189(4) 0.4155(2) 0.0004(5) 0.0534(8) 1.000 . Uani d ? C(19) 0.7575(5) 0.4902(2) -0.2875(6) 0.076(1) 1.000 . Uani d ? H(1) -0.0602 0.2365 -0.1533 0.064 1.000 . Uiso c ? H(2) -0.1073 0.2531 0.0770 0.064 1.000 . Uiso c ? H(3) -0.2552 0.1546 -0.0943 0.075 1.000 . Uiso c ? H(4) -0.0799 0.1064 -0.1360 0.075 1.000 . Uiso c ? H(5) -0.1451 0.1180 0.2860 0.080 1.000 . Uiso c ? H(6) -0.1179 0.0397 0.1513 0.080 1.000 . Uiso c ? H(7) 0.1400 0.0466 0.4904 0.072 1.000 . Uiso c ? H(8) 0.1920 0.0364 0.2621 0.072 1.000 . Uiso c ? H(9) 0.0959 0.1833 0.4375 0.057 1.000 . Uiso c ? H(10) 0.3948 0.1875 0.6281 0.056 1.000 . Uiso c ? H(11) 0.5159 0.0664 0.4722 0.067 1.000 . Uiso c ? H(12) 0.6170 0.1367 0.4664 0.067 1.000 . Uiso c ? H(13) 0.4906 0.0583 0.1102 0.085 1.000 . Uiso c ? H(14) 0.5251 0.1453 0.0918 0.085 1.000 . Uiso c ? H(15) 0.2489 0.1726 -0.1281 0.061 1.000 . Uiso c ? H(16) 0.2044 0.0955 -0.0397 0.061 1.000 . Uiso c ? H(17) 0.5884 0.2791 0.5228 0.062 1.000 . Uiso c ? H(18) 0.7612 0.3487 0.3946 0.078 1.000 . Uiso c ? H(19) 0.3920 0.3895 -0.2388 0.068 1.000 . Uiso c ? H(20) 0.2173 0.3161 -0.1260 0.078 1.000 . Uiso c ? H(21) 0.8693 0.4547 -0.2801 0.091 1.000 . Uiso c ? H(22) 0.7847 0.5341 -0.1888 0.091 1.000 . Uiso c ? H(23) 0.1031 0.3369 0.3111 0.069 1.000 . Uiso c ? H(24) 0.6925 0.5104 -0.4464 0.091 1.000 . Uiso c ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.051(1) 0.064(1) 0.042(1) -0.0037(9) 0.0082(8) -0.0124(8) O(2) 0.058(1) 0.079(2) 0.086(2) -0.029(1) -0.002(1) 0.017(1) O(3) 0.070(1) 0.071(1) 0.054(1) -0.031(1) 0.010(1) 0.006(1) C(1) 0.049(2) 0.062(2) 0.043(1) -0.017(1) 0.015(1) -0.011(1) C(2) 0.050(2) 0.089(2) 0.066(2) -0.003(2) 0.015(1) -0.024(2) C(3) 0.042(1) 0.061(2) 0.056(2) -0.008(1) 0.005(1) 0.004(1) C(4) 0.039(1) 0.064(2) 0.032(1) -0.014(1) 0.003(1) 0.000(1) C(5) 0.040(1) 0.061(2) 0.038(1) -0.011(1) 0.008(1) 0.002(1) C(6) 0.054(2) 0.069(2) 0.055(2) -0.019(1) 0.011(1) 0.008(1) C(7) 0.054(2) 0.080(2) 0.068(2) -0.029(2) 0.013(2) -0.004(2) C(8) 0.043(2) 0.083(2) 0.055(2) -0.020(1) 0.003(1) -0.006(2) C(9) 0.041(1) 0.069(2) 0.041(1) -0.009(1) 0.001(1) 0.000(1) C(10) 0.038(1) 0.052(1) 0.032(1) -0.010(1) 0.005(1) -0.002(1) C(11) 0.039(1) 0.053(1) 0.030(1) -0.007(1) 0.004(1) -0.006(1) C(12) 0.046(1) 0.049(1) 0.034(1) -0.010(1) 0.004(1) -0.004(1) C(13) 0.045(1) 0.058(2) 0.039(1) -0.015(1) 0.001(1) 0.001(1) C(14) 0.053(2) 0.053(2) 0.040(1) -0.013(1) 0.004(1) 0.002(1) C(15) 0.048(1) 0.043(1) 0.048(1) -0.011(1) 0.010(1) -0.004(1) C(16) 0.046(1) 0.056(2) 0.043(1) -0.016(1) 0.001(1) -0.004(1) C(17) 0.050(2) 0.061(2) 0.036(1) -0.016(1) 0.002(1) -0.002(1) C(18) 0.052(2) 0.042(1) 0.062(2) -0.010(1) 0.011(1) -0.002(1) C(19) 0.091(3) 0.077(2) 0.069(2) -0.039(2) 0.027(2) 0.001(2) #------------------------------------------------------------------------------ _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_weighting_details unit _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method 'Zachariasen (1967)' _refine_ls_extinction_coef 0.000048(1) _refine_ls_extinction_expression 'equ(3) Acta Cryst.(1968) A24, p213.' _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 2814 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.0706 _refine_ls_R_factor_gt 0.0600 _refine_ls_wR_factor_all 0.0694 _refine_ls_wR_factor_ref 0.0604 _refine_ls_goodness_of_fit_all 3.602 _refine_ls_goodness_of_fit_ref 3.393 _refine_ls_shift/su_max 0.0001 _refine_ls_shift/su_mean 0.0002 _refine_diff_density_min -0.24 _refine_diff_density_max 0.25 #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O(1) C(11) 1.428(3) . . yes O(1) H(23) 0.81 . . no O(2) C(18) 1.217(3) . . yes O(3) C(18) 1.322(3) . . yes O(3) C(19) 1.441(4) . . yes C(1) C(2) 1.542(4) . . yes C(1) C(10) 1.522(3) . . yes C(1) H(1) 0.98 . . no C(1) H(2) 0.98 . . no C(2) C(3) 1.528(4) . . yes C(2) H(3) 0.98 . . no C(2) H(4) 0.98 . . no C(3) C(4) 1.551(4) . . yes C(3) H(5) 0.98 . . no C(3) H(6) 0.98 . . no C(4) C(5) 1.505(4) . . yes C(4) H(7) 0.98 . . no C(4) H(8) 0.98 . . no C(5) C(6) 1.554(3) . . yes C(5) C(10) 1.541(3) . . yes C(5) H(9) 0.98 . . no C(6) C(7) 1.515(4) . . yes C(6) C(11) 1.562(3) . . yes C(6) H(10) 0.98 . . no C(7) C(8) 1.533(4) . . yes C(7) H(11) 0.98 . . no C(7) H(12) 0.98 . . no C(8) C(9) 1.524(4) . . yes C(8) H(13) 0.98 . . no C(8) H(14) 0.98 . . no C(9) C(10) 1.527(4) . . yes C(9) H(15) 0.98 . . no C(9) H(16) 0.98 . . no C(10) C(11) 1.586(3) . . yes C(11) C(12) 1.492(4) . . yes C(12) C(13) 1.387(3) . . yes C(12) C(17) 1.408(3) . . yes C(13) C(14) 1.375(4) . . yes C(13) H(20) 0.97 . . no C(14) C(15) 1.402(4) . . yes C(14) H(19) 0.98 . . no C(15) C(16) 1.385(4) . . yes C(15) C(18) 1.473(4) . . yes C(16) C(17) 1.369(4) . . yes C(16) H(18) 0.91 . . no C(17) H(17) 1.00 . . no C(19) H(21) 0.98 . . no C(19) H(22) 0.98 . . no C(19) H(24) 0.98 . . no #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(11) O(1) H(23) 111.3 . . . no C(18) O(3) C(19) 117.0(2) . . . yes C(2) C(1) C(10) 107.9(2) . . . yes C(2) C(1) H(1) 109.8 . . . no C(2) C(1) H(2) 109.8 . . . no C(10) C(1) H(1) 109.9 . . . no C(10) C(1) H(2) 109.9 . . . no H(1) C(1) H(2) 109.5 . . . no C(1) C(2) C(3) 115.4(2) . . . yes C(1) C(2) H(3) 108.0 . . . no C(1) C(2) H(4) 108.0 . . . no C(3) C(2) H(3) 108.0 . . . no C(3) C(2) H(4) 108.0 . . . no H(3) C(2) H(4) 109.5 . . . no C(2) C(3) C(4) 115.2(2) . . . yes C(2) C(3) H(5) 108.0 . . . no C(2) C(3) H(6) 108.0 . . . no C(4) C(3) H(5) 108.0 . . . no C(4) C(3) H(6) 108.0 . . . no H(5) C(3) H(6) 109.5 . . . no C(3) C(4) C(5) 104.1(2) . . . yes C(3) C(4) H(7) 110.8 . . . no C(3) C(4) H(8) 110.8 . . . no C(5) C(4) H(7) 110.8 . . . no C(5) C(4) H(8) 110.8 . . . no H(7) C(4) H(8) 109.5 . . . no C(4) C(5) C(6) 132.5(2) . . . yes C(4) C(5) C(10) 113.7(2) . . . yes C(4) C(5) H(9) 106.8 . . . no C(6) C(5) C(10) 87.0(2) . . . yes C(6) C(5) H(9) 106.8 . . . no C(10) C(5) H(9) 106.8 . . . no C(5) C(6) C(7) 111.4(2) . . . yes C(5) C(6) C(11) 85.8(2) . . . yes C(5) C(6) H(10) 114.3 . . . no C(7) C(6) C(11) 113.6(2) . . . yes C(7) C(6) H(10) 114.3 . . . no C(11) C(6) H(10) 114.3 . . . no C(6) C(7) C(8) 111.9(2) . . . yes C(6) C(7) H(11) 108.9 . . . no C(6) C(7) H(12) 108.9 . . . no C(8) C(7) H(11) 108.9 . . . no C(8) C(7) H(12) 108.9 . . . no H(11) C(7) H(12) 109.5 . . . no C(7) C(8) C(9) 113.8(2) . . . yes C(7) C(8) H(13) 108.4 . . . no C(7) C(8) H(14) 108.4 . . . no C(9) C(8) H(13) 108.3 . . . no C(9) C(8) H(14) 108.4 . . . no H(13) C(8) H(14) 109.5 . . . no C(8) C(9) C(10) 114.9(2) . . . yes C(8) C(9) H(15) 108.1 . . . no C(8) C(9) H(16) 108.1 . . . no C(10) C(9) H(15) 108.1 . . . no C(10) C(9) H(16) 108.1 . . . no H(15) C(9) H(16) 109.5 . . . no C(1) C(10) C(5) 109.9(2) . . . yes C(1) C(10) C(9) 111.7(2) . . . yes C(1) C(10) C(11) 126.6(2) . . . yes C(5) C(10) C(9) 110.9(2) . . . yes C(5) C(10) C(11) 85.5(2) . . . yes C(9) C(10) C(11) 109.0(2) . . . yes O(1) C(11) C(6) 106.8(2) . . . yes O(1) C(11) C(10) 112.1(2) . . . yes O(1) C(11) C(12) 108.3(2) . . . yes C(6) C(11) C(10) 85.2(2) . . . yes C(6) C(11) C(12) 120.3(2) . . . yes C(10) C(11) C(12) 122.1(2) . . . yes C(11) C(12) C(13) 123.5(2) . . . yes C(11) C(12) C(17) 119.1(2) . . . yes C(13) C(12) C(17) 117.3(2) . . . yes C(12) C(13) C(14) 122.0(2) . . . yes C(12) C(13) H(20) 120.5 . . . no C(14) C(13) H(20) 117.4 . . . no C(13) C(14) C(15) 119.9(2) . . . yes C(13) C(14) H(19) 121.8 . . . no C(15) C(14) H(19) 118.1 . . . no C(14) C(15) C(16) 118.7(2) . . . yes C(14) C(15) C(18) 122.3(2) . . . yes C(16) C(15) C(18) 119.0(2) . . . yes C(15) C(16) C(17) 121.0(2) . . . yes C(15) C(16) H(18) 120.3 . . . no C(17) C(16) H(18) 118.7 . . . no C(12) C(17) C(16) 121.1(2) . . . yes C(12) C(17) H(17) 117.1 . . . no C(16) C(17) H(17) 121.9 . . . no O(2) C(18) O(3) 122.2(3) . . . yes O(2) C(18) C(15) 123.6(3) . . . yes O(3) C(18) C(15) 114.1(2) . . . yes O(3) C(19) H(21) 109.5 . . . no O(3) C(19) H(22) 109.5 . . . no O(3) C(19) H(24) 109.5 . . . no H(21) C(19) H(22) 109.5 . . . no H(21) C(19) H(24) 109.5 . . . no H(22) C(19) H(24) 109.5 . . . no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O(1) O(2) 2.917(3) . 1_455 no O(1) C(14) 3.426(3) . 1_556 no O(1) C(13) 3.427(3) . 1_556 no O(2) C(19) 3.502(4) . 2_765 no O(3) C(16) 3.577(3) . 1_554 no #------------------------------------------------------------------------------ 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O(1) C(11) C(6) C(5) . . . . 82.0(2) no O(1) C(11) C(6) C(7) . . . . -166.5(2) no O(1) C(11) C(6) H(10) . . . . -32.8(3) no O(1) C(11) C(10) C(1) . . . . 35.3(3) no O(1) C(11) C(10) C(5) . . . . -76.2(2) no O(1) C(11) C(10) C(9) . . . . 173.2(2) no O(1) C(11) C(12) C(13) . . . . -94.1(3) no O(1) C(11) C(12) C(17) . . . . 82.2(3) no O(2) C(18) O(3) C(19) . . . . -0.2(4) no O(2) C(18) C(15) C(14) . . . . -173.8(3) no O(2) C(18) C(15) C(16) . . . . 4.1(4) no O(3) C(18) C(15) C(14) . . . . 6.2(4) no O(3) C(18) C(15) C(16) . . . . -175.8(3) no C(1) C(2) C(3) C(4) . . . . -49.6(4) no C(1) C(2) C(3) H(5) . . . . 71.2(3) no C(1) C(2) C(3) H(6) . . . . -170.5(3) no C(1) C(10) C(5) C(4) . . . . 66.8(3) no C(1) C(10) C(5) C(6) . . . . -157.5(2) no C(1) C(10) C(5) H(9) . . . . -50.8(3) no C(1) C(10) C(9) C(8) . . . . -176.8(3) no C(1) C(10) C(9) H(15) . . . . 62.4(3) no C(1) C(10) C(9) H(16) . . . . -56.0(3) no C(1) C(10) C(11) C(6) . . . . 141.4(3) no C(1) C(10) C(11) C(12) . . . . -95.6(3) no C(2) C(1) C(10) C(5) . . . . -54.7(3) no C(2) C(1) C(10) C(9) . . . . 68.8(3) no C(2) C(1) C(10) C(11) . . . . -154.2(2) no C(2) C(3) C(4) C(5) . . . . 51.9(3) no C(2) C(3) C(4) H(7) . . . . 171.0(3) no C(2) C(3) C(4) H(8) . . . . -67.2(4) no C(3) C(2) C(1) C(10) . . . . 48.5(3) no C(3) C(2) C(1) H(1) . . . . 168.3(3) no C(3) C(2) C(1) H(2) . . . . -71.2(3) no C(3) C(4) C(5) C(6) . . . . -169.9(3) no C(3) C(4) C(5) C(10) . . . . -61.0(3) no C(3) C(4) C(5) H(9) . . . . 56.6(3) no C(4) C(3) C(2) H(3) . . . . -170.5(3) no C(4) C(3) C(2) H(4) . . . . 71.3(3) no C(4) C(5) C(6) C(7) . . . . 36.6(4) no C(4) C(5) C(6) C(11) . . . . 150.4(3) no C(4) C(5) C(6) H(10) . . . . -94.8(4) no C(4) C(5) C(10) C(9) . . . . -57.1(3) no C(4) C(5) C(10) C(11) . . . . -165.7(2) no C(5) C(4) C(3) H(5) . . . . -68.9(3) no C(5) C(4) C(3) H(6) . . . . 172.7(3) no C(5) C(6) C(7) C(8) . . . . 59.0(3) no C(5) C(6) C(7) H(11) . . . . -61.4(3) no C(5) C(6) C(7) H(12) . . . . 179.4(2) no C(5) C(6) C(11) C(10) . . . . -29.7(2) no C(5) C(6) C(11) C(12) . . . . -154.2(2) no C(5) C(10) C(1) H(1) . . . . -174.5(2) no C(5) C(10) C(1) H(2) . . . . 65.0(3) no C(5) C(10) C(9) C(8) . . . . -53.9(3) no C(5) C(10) C(9) H(15) . . . . -174.7(2) no C(5) C(10) C(9) H(16) . . . . 66.9(3) no C(5) C(10) C(11) C(6) . . . . 30.0(2) no C(5) C(10) C(11) C(12) . . . . 152.9(2) no C(6) C(5) C(4) H(7) . . . . 70.9(4) no C(6) C(5) C(4) H(8) . . . . -50.8(4) no C(6) C(5) C(10) C(9) . . . . 78.6(2) no C(6) C(5) C(10) C(11) . . . . -30.1(2) no C(6) C(7) C(8) C(9) . . . . -19.5(4) no C(6) C(7) C(8) H(13) . . . . -140.1(3) no C(6) C(7) C(8) H(14) . . . . 101.2(3) no C(6) C(11) O(1) H(23) . . . . -162.8(2) no C(6) C(11) C(10) C(9) . . . . -80.6(2) no C(6) C(11) C(12) C(13) . . . . 142.9(3) no C(6) C(11) C(12) C(17) . . . . -40.8(3) no C(7) C(6) C(5) C(10) . . . . -83.3(2) no C(7) C(6) C(5) H(9) . . . . 170.1(2) no C(7) C(6) C(11) C(10) . . . . 81.9(2) no C(7) C(6) C(11) C(12) . . . . -42.7(3) no C(7) C(8) C(9) C(10) . . . . 17.6(4) no C(7) C(8) C(9) H(15) . . . . 138.4(3) no C(7) C(8) C(9) H(16) . . . . -103.2(3) no C(8) C(7) C(6) C(11) . . . . -35.9(3) no C(8) C(7) C(6) H(10) . . . . -169.6(3) no C(8) C(9) C(10) C(11) . . . . 38.5(3) no C(9) C(8) C(7) H(11) . . . . 100.9(3) no C(9) C(8) C(7) H(12) . . . . -139.9(3) no C(9) C(10) C(1) H(1) . . . . -51.0(3) no C(9) C(10) C(1) H(2) . . . . -171.5(2) no C(9) C(10) C(5) H(9) . . . . -174.7(2) no C(9) C(10) C(11) C(12) . . . . 42.3(3) no C(10) C(1) C(2) H(3) . . . . 169.4(2) no C(10) C(1) C(2) H(4) . . . . -72.3(3) no C(10) C(5) C(4) H(7) . . . . 179.9(2) no C(10) C(5) C(4) H(8) . . . . 58.2(3) no C(10) C(5) C(6) C(11) . . . . 30.5(2) no C(10) C(5) C(6) H(10) . . . . 145.3(3) no C(10) C(9) C(8) H(13) . . . . 138.2(3) no C(10) C(9) C(8) H(14) . . . . -103.1(3) no C(10) C(11) O(1) H(23) . . . . -71.3(3) no C(10) C(11) C(6) H(10) . . . . -144.5(2) no C(10) C(11) C(12) C(13) . . . . 38.4(4) no C(10) C(11) C(12) C(17) . . . . -145.3(2) no C(11) C(6) C(5) H(9) . . . . -76.1(2) no C(11) C(6) C(7) H(11) . . . . -156.3(2) no C(11) C(6) C(7) H(12) . . . . 84.4(3) no C(11) C(10) C(1) H(1) . . . . 86.1(3) no C(11) C(10) C(1) H(2) . . . . -34.4(4) no C(11) C(10) C(5) H(9) . . . . 76.6(2) no C(11) C(10) C(9) H(15) . . . . -82.3(3) no C(11) C(10) C(9) H(16) . . . . 159.4(2) no C(11) C(12) C(13) C(14) . . . . 176.8(3) no C(11) C(12) C(13) H(20) . . . . -2.8(4) no C(11) C(12) C(17) C(16) . . . . -177.7(3) no C(11) C(12) C(17) H(17) . . . . 2.6(4) no C(12) C(11) O(1) H(23) . . . . 66.3(3) no C(12) C(11) C(6) H(10) . . . . 90.9(3) no C(12) C(13) C(14) C(15) . . . . 0.0(4) no C(12) C(13) C(14) H(19) . . . . -174.6(3) no C(12) C(17) C(16) C(15) . . . . 1.5(4) no C(12) C(17) C(16) H(18) . . . . 179.4(3) no C(13) C(12) C(17) C(16) . . . . -1.1(4) no C(13) C(12) C(17) H(17) . . . . 179.2(3) no C(13) C(14) C(15) C(16) . . . . 0.3(4) no C(13) C(14) C(15) C(18) . . . . 178.3(3) no C(14) C(13) C(12) C(17) . . . . 0.4(4) no C(14) C(15) C(16) C(17) . . . . -1.1(4) no C(14) C(15) C(16) H(18) . . . . -178.9(3) no C(15) C(14) C(13) H(20) . . . . 179.6(3) no C(15) C(16) C(17) H(17) . . . . -178.8(3) no C(15) C(18) O(3) C(19) . . . . 179.7(3) no C(16) C(15) C(14) H(19) . . . . 175.1(3) no C(17) C(12) C(13) H(20) . . . . -179.2(3) no C(17) C(16) C(15) C(18) . . . . -179.1(3) no C(18) O(3) C(19) H(21) . . . . 58.6(4) no C(18) O(3) C(19) H(22) . . . . -61.4(4) no C(18) O(3) C(19) H(24) . . . . 178.6(3) no C(18) C(15) C(14) H(19) . . . . -6.9(4) no C(18) C(15) C(16) H(18) . . . . 3.1(4) no H(1) C(1) C(2) H(3) . . . . -70.8(3) no H(1) C(1) C(2) H(4) . . . . 47.5(3) no H(2) C(1) C(2) H(3) . . . . 49.7(3) no H(2) C(1) C(2) H(4) . . . . 167.9(2) no H(3) C(2) C(3) H(5) . . . . -49.6(4) no H(3) C(2) C(3) H(6) . . . . 68.7(4) no H(4) C(2) C(3) H(5) . . . . -167.9(2) no H(4) C(2) C(3) H(6) . . . . -49.6(4) no H(5) C(3) C(4) H(7) . . . . 50.2(4) no H(5) C(3) C(4) H(8) . . . . 171.9(3) no H(6) C(3) C(4) H(7) . . . . -68.1(4) no H(6) C(3) C(4) H(8) . . . . 53.6(4) no H(7) C(4) C(5) H(9) . . . . -62.5(3) no H(8) C(4) C(5) H(9) . . . . 175.8(2) no H(9) C(5) C(6) H(10) . . . . 38.7(3) no H(10) C(6) C(7) H(11) . . . . 70.0(3) no H(10) C(6) C(7) H(12) . . . . -49.2(3) no H(11) C(7) C(8) H(13) . . . . -19.8(4) no H(11) C(7) C(8) H(14) . . . . -138.5(3) no H(12) C(7) C(8) H(13) . . . . 99.5(3) no H(12) C(7) C(8) H(14) . . . . -19.2(4) no H(13) C(8) C(9) H(15) . . . . -101.0(3) no H(13) C(8) C(9) H(16) . . . . 17.4(4) no H(14) C(8) C(9) H(15) . . . . 17.7(4) no H(14) C(8) C(9) H(16) . . . . 136.1(3) no H(17) C(17) C(16) H(18) . . . . -0.9(5) no H(19) C(14) C(13) H(20) . . . . 5.0(5) no #------------------------------------------------------------------------------