# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 137237 data_Y-11 _database_code_CSD 137237 #------------------------------------------------------------------------------ _audit_creation_method 'by teXsan v1.7' #------------------------------------------------------------------------------ _publ_requested_journal ' Perkins Trans 1' _journal_coden_Cambridge 207 _publ_contact_author ; Masood Parvez Department of Chemistry University of Calgary 2500 University Drive, N.W. Calgary, Alberta Canada T2N 1N4 ; _publ_contact_author_phone ' (403) 220 5348 ' _publ_contact_author_fax ' 403 289 9488 ' _publ_contact_author_email ' parvez@ucalgary.ca ' #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan (MSC, 1995)' _computing_structure_solution ; SIR92 (Altomare, et. al. 1993) ; _computing_structure_refinement 'teXsan (MSC, 1995)' _computing_publication_material 'teXsan (MSC, 1995)' #------------------------------------------------------------------------------ _cell_length_a 5.845(5) _cell_length_b 17.134(4) _cell_length_c 7.935(7) _cell_angle_alpha 90 _cell_angle_beta 107.54(6) _cell_angle_gamma 90 _cell_volume 757.7(9) _cell_formula_units_Z 2 _cell_measurement_temperature 170 _cell_measurement_reflns_used 12 _cell_measurement_theta_min 7.0 _cell_measurement_theta_max 8.2 #------------------------------------------------------------------------------ _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n ' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' '1/2-x,1/2+y,1/2-z' ' -x, -y, -z' '1/2+x,1/2-y,1/2+z' #------------------------------------------------------------------------------ _exptl_crystal_description 'plate' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.41 _exptl_crystal_size_min 0.16 _exptl_crystal_density_diffrn 1.299 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 296.32 _chemical_formula_sum 'C18 H16 O4 ' _chemical_formula_moiety 'C18 H16 O4 ' _exptl_crystal_F_000 312.00 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type ; \y scans (North,Phillips & Matthews, 1968) ; _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.976 #------------------------------------------------------------------------------ _diffrn_ambient_temperature 170 _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 'Rigaku AFC6S' _diffrn_measurement_method \w-2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_decay_% 1.23 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 2 3 0 1 5 -1 1 4 1 _diffrn_reflns_number 1533 _reflns_number_total 1395 _reflns_number_observed 609 _reflns_observed_criterion >3.00\s(I) _diffrn_reflns_av_R_equivalents 0.03735 _diffrn_reflns_av_sigmaI/netI 0.110 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.69 _diffrn_reflns_theta_max 25.05 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 -0.00280 _diffrn_orient_matrix_UB_12 0.05760 _diffrn_orient_matrix_UB_13 0.01965 _diffrn_orient_matrix_UB_21 0.11877 _diffrn_orient_matrix_UB_22 -0.00644 _diffrn_orient_matrix_UB_23 0.11980 _diffrn_orient_matrix_UB_31 0.13445 _diffrn_orient_matrix_UB_32 0.00689 _diffrn_orient_matrix_UB_33 -0.05226 #------------------------------------------------------------------------------ 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 36 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H 0 32 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; O 0 8 0.011 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_occupancy _atom_site_refinement_flags _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom O(1) 0.3511(8) 0.0760(3) 0.2116(6) 0.0516(17) 1.000 . Uani d ? O(2) 0.0264(8) 0.0499(3) 0.2901(6) 0.0498(18) 1.000 . Uani d ? C(1) 0.4972(16) 0.0969(4) 0.6237(9) 0.058(3) 1.000 . Uani d ? C(2) 0.3658(15) 0.1152(5) 0.7361(10) 0.059(3) 1.000 . Uani d ? C(3) 0.4143(14) 0.1808(5) 0.8378(9) 0.050(3) 1.000 . Uani d ? C(4) 0.5930(14) 0.2300(4) 0.8307(10) 0.050(3) 1.000 . Uani d ? C(5) 0.7284(13) 0.2131(4) 0.7199(10) 0.052(3) 1.000 . Uani d ? C(6) 0.6773(15) 0.1474(5) 0.6144(9) 0.055(3) 1.000 . Uani d ? C(7) 0.3933(13) 0.0188(5) 0.4995(11) 0.065(3) 1.000 . Uani d ? C(8) 0.2603(12) 0.0497(4) 0.3148(9) 0.036(2) 1.000 . Uani d ? C(9) -0.1244(12) 0.0833(4) 0.1272(9) 0.052(3) 1.000 . Uani d ? H(2) 0.2396 0.0816 0.7428 0.070 1.000 . Uiso c ? H(3) 0.3218 0.1923 0.9147 0.060 1.000 . Uiso c ? H(4) 0.6248 0.2758 0.9016 0.060 1.000 . Uiso c ? H(5) 0.8564 0.2466 0.7161 0.063 1.000 . Uiso c ? H(6) 0.7666 0.1369 0.5349 0.066 1.000 . Uiso c ? H(91) -0.0811 0.1363 0.1195 0.063 1.000 . Uiso c ? H(92) -0.1037 0.0550 0.0298 0.063 1.000 . Uiso c ? H(93) -0.2875 0.0804 0.1252 0.063 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) 0.036(3) 0.072(4) 0.049(3) 0.005(3) 0.015(3) 0.021(3) O(2) 0.039(3) 0.062(4) 0.044(3) 0.006(3) 0.006(3) 0.021(3) C(1) 0.120(8) 0.028(5) 0.029(5) -0.006(5) 0.025(5) 0.003(4) C(2) 0.086(7) 0.051(6) 0.037(5) -0.023(5) 0.015(5) 0.005(4) C(3) 0.057(6) 0.052(6) 0.038(5) 0.008(5) 0.010(4) -0.003(4) C(4) 0.071(6) 0.020(5) 0.050(5) -0.001(4) 0.006(5) -0.008(4) C(5) 0.051(5) 0.048(6) 0.054(6) -0.009(5) 0.010(4) 0.008(5) C(6) 0.083(7) 0.042(5) 0.052(5) 0.015(5) 0.037(5) 0.009(5) C(7) 0.046(5) 0.094(8) 0.049(5) 0.020(5) 0.004(5) 0.035(5) C(8) 0.031(5) 0.036(5) 0.039(5) 0.005(4) 0.008(4) -0.003(4) C(9) 0.038(5) 0.067(6) 0.044(5) 0.009(5) 0.000(4) 0.004(5) #------------------------------------------------------------------------------ _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme 'w = 1/[\s^2^(Fo)]' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_number_reflns 609 _refine_ls_number_parameters 100 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.0759 _refine_ls_R_factor_obs 0.0759 _refine_ls_wR_factor_all 0.0507 _refine_ls_wR_factor_obs 0.0507 _refine_ls_goodness_of_fit_all 3.334 _refine_ls_goodness_of_fit_obs 3.334 _refine_ls_shift/esd_max 0.0000 _refine_ls_shift/esd_mean 0.0000 _refine_diff_density_min -0.43 _refine_diff_density_max 0.60 #------------------------------------------------------------------------------ _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(8) 1.190(7) . . yes O(2) C(8) 1.321(7) . . yes O(2) C(9) 1.445(7) . . yes C(1) C(2) 1.377(10) . . yes C(1) C(6) 1.382(10) . . yes C(1) C(7) 1.664(11) . . yes C(2) C(3) 1.363(9) . . yes C(2) H(2) 0.95 . . no C(3) C(4) 1.356(10) . . yes C(3) H(3) 0.95 . . no C(4) C(5) 1.380(9) . . yes C(4) H(4) 0.95 . . no C(5) C(6) 1.381(9) . . yes C(5) H(5) 0.95 . . no C(6) H(6) 0.95 . . no C(7) C(7) 1.402(14) . 3_656 yes C(7) C(8) 1.531(9) . . yes C(9) H(91) 0.95 . . no C(9) H(92) 0.95 . . no C(9) H(93) 0.95 . . 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(8) O(2) C(9) 117.3(5) . . . yes C(2) C(1) C(6) 118.3(7) . . . yes C(2) C(1) C(7) 113.0(7) . . . yes C(6) C(1) C(7) 128.3(7) . . . yes C(1) C(2) C(3) 120.9(8) . . . yes C(1) C(2) H(2) 119.5 . . . no C(3) C(2) H(2) 119.5 . . . no C(2) C(3) C(4) 120.9(8) . . . yes C(2) C(3) H(3) 119.6 . . . no C(4) C(3) H(3) 119.6 . . . no C(3) C(4) C(5) 119.6(7) . . . yes C(3) C(4) H(4) 120.2 . . . no C(5) C(4) H(4) 120.2 . . . no C(4) C(5) C(6) 119.7(7) . . . yes C(4) C(5) H(5) 120.1 . . . no C(6) C(5) H(5) 120.1 . . . no C(1) C(6) C(5) 120.5(7) . . . yes C(1) C(6) H(6) 119.7 . . . no C(5) C(6) H(6) 119.7 . . . no C(1) C(7) C(7) 101.6(9) . . 3_656 yes C(1) C(7) C(8) 106.1(6) . . . yes C(7) C(7) C(8) 111.0(9) 3_656 . . yes O(1) C(8) O(2) 123.6(6) . . . yes O(1) C(8) C(7) 125.9(7) . . . yes O(2) C(8) C(7) 110.3(6) . . . yes O(2) C(9) H(91) 109.5 . . . no O(2) C(9) H(92) 109.5 . . . no O(2) C(9) H(93) 109.5 . . . no H(91) C(9) H(92) 109.5 . . . no H(91) C(9) H(93) 109.5 . . . no H(92) C(9) H(93) 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(9) 3.332(8) . 1_655 no O(1) C(3) 3.580(9) . 1_554 no O(2) C(7) 3.559(9) . 3_556 no C(3) C(9) 3.407(10) . 1_656 no C(4) C(9) 3.499(10) . 1_656 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(8) O(2) C(9) . . . . 0.8(11) no O(1) C(8) C(7) C(1) . . . . 73.7(9) no O(1) C(8) C(7) C(7) . . . 3_656 -35.9(14) no O(2) C(8) C(7) C(1) . . . . -100.6(7) no O(2) C(8) C(7) C(7) . . . 3_656 149.8(10) no C(1) C(2) C(3) C(4) . . . . 0.2(13) no C(1) C(6) C(5) C(4) . . . . -2.3(12) no C(1) C(7) C(7) C(1) . . 3_656 3_656 -180.0000 no C(1) C(7) C(7) C(8) . . 3_656 3_656 67.5(10) no C(2) C(1) C(6) C(5) . . . . 2.1(12) no C(2) C(1) C(7) C(7) . . . 3_656 -140.0(8) no C(2) C(1) C(7) C(8) . . . . 103.8(7) no C(2) C(3) C(4) C(5) . . . . -0.4(12) no C(3) C(2) C(1) C(6) . . . . -1.0(12) no C(3) C(2) C(1) C(7) . . . . -175.0(7) no C(3) C(4) C(5) C(6) . . . . 1.5(12) no C(5) C(6) C(1) C(7) . . . . 175.0(7) no C(6) C(1) C(7) C(7) . . . 3_656 46.7(11) no C(6) C(1) C(7) C(8) . . . . -69.4(10) no C(7) C(8) O(2) C(9) . . . . 175.2(6) no C(8) C(7) C(7) C(8) . . 3_656 3_656 180.0000 no #------------------------------------------------------------------------------ #---- End Included Message ----- #---- End Included Message -----