Supplementary Material (ESI) for Perkin Transactions This journal is © The Royal Society of Chemistry 2001 ---------- X-Sun-Content-Length: 66035 X-Sun-Charset: us-ascii X-Sun-Content-Lines: 1797 data_General #============================================================================== _audit_creation_date '2001-04-05' _audit_creation_method 'by teXsan for Windows v1.06' _audit_update_record ? #============================================================================== # SUBMISSION DETAILS _publ_requested_journal ' Perkin Transactions 1' _journal_coden_Cambridge 207 _publ_contact_author_name ' Prof D J Burnell' _publ_contact_author_address ; Prof D J Burnell Department of Chemistry Memorial University of Newfoundland St. John's, Newfoundland Canada A1B 3X7 ; _publ_contact_author_phone '709 737 8535' _publ_contact_author_fax '709 737 3702' _publ_contact_author_email 'jburnell@mun.ca' #============================================================================== # PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #============================================================================== # TITLE AND AUTHOR LIST _publ_section_title ; Synthetic studies toward the kempane diterpenes. Diels-Alder additions to bicyclic dienes ; loop_ _publ_author_name _publ_author_address 'Bao, Guanglin' ? ' D. Jean Burnell' ; Department of Chemistry, Memorial University of Newfoundland, St. John's, Newfoundland, Canada A1B 3X7 ; 'Liu, Chunjian' ? #============================================================================== # TEXT _publ_section_references ; ENTER OTHER REFERENCES Molecular Structure Corporation. (1997-1999). teXsan for Windows. Single Crystal Structure Analysis Software. Version 1.06. MSC, 9009 New Trails 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. (1994). J. Appl. Cryst., 26, 343. Zachariasen, W. H. (1967). Acta Cryst. 23, 558-564. ; #============================================================================== data_gb-2-22-2 _database_code_CSD 164940 #============================================================================== _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan for Windows version 1.06 (MSC, 1997-1999)' _computing_structure_solution ; SIR92 (Altomare, et. al. 1994) ; _computing_structure_refinement 'teXsan for Windows version 1.06 (MSC, 1997-1999)' _computing_publication_material 'teXsan for Windows version 1.06 (MSC, 1997-1999)' #------------------------------------------------------------------------------ _cell_length_a 21.765(7) _cell_length_b 14.725(6) _cell_length_c 11.857(6) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 3800(2) _cell_formula_units_Z 8 _cell_measurement_temperature 299.2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 29.1 _cell_measurement_theta_max 29.9 #------------------------------------------------------------------------------ _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a ' _symmetry_Int_Tables_number 61 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' '1/2+x,1/2-y, -z' ' -x,1/2+y,1/2-z' '1/2-x, -y,1/2+z' ' -x, -y, -z' '1/2-x,1/2+y, +z' ' +x,1/2-y,1/2+z' '1/2+x, +y,1/2-z' #------------------------------------------------------------------------------ _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _exptl_crystal_description 'irregular' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.330 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 380.56 _chemical_formula_analytical ? _chemical_formula_sum 'C20 H28 O3 S2 ' _chemical_formula_moiety 'C20 H28 O3 S2 ' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 1632.00 _exptl_absorpt_coefficient_mu 2.667 _exptl_absorpt_correction_type ; \y scans (North,Phillips & Matthews, 1968) ; _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.746 _exptl_special_details ; The scan width was (1.47+0.14tan\q)\% with an \w scan speed of 4\% per minute (up to 11 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. ; #============================================================================== # EXPERIMENTAL DATA _diffrn_special_details ; ? ; _diffrn_ambient_temperature 299.2 _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 'Rigaku AFC6S' _diffrn_measurement_method \w-2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 0.79 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -4 -1 -1 -4 1 -1 -3 -2 -2 _diffrn_reflns_number 3219 _reflns_number_total 3219 _reflns_number_gt 2257 _reflns_threshold_expression I>2.00\s(I) _diffrn_reflns_av_R_equivalents 0.00000 _diffrn_reflns_av_sigmaI/netI 0.049 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 60.02 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 0.01363 _diffrn_orient_matrix_UB_12 -0.03115 _diffrn_orient_matrix_UB_13 0.07064 _diffrn_orient_matrix_UB_21 -0.04382 _diffrn_orient_matrix_UB_22 -0.00658 _diffrn_orient_matrix_UB_23 0.02402 _diffrn_orient_matrix_UB_31 -0.00227 _diffrn_orient_matrix_UB_32 -0.05999 _diffrn_orient_matrix_UB_33 0.00000 #------------------------------------------------------------------------------ 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 0 160 0.017 0.009 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; H 0 224 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; O 0 24 0.047 0.032 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; S 0 16 0.319 0.557 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 S(1) 0.45460(4) 0.44342(6) 0.30227(7) 0.0616(3) 1.000 . Uani d ? S(2) 0.47638(4) 0.28079(6) 0.15396(7) 0.0571(3) 1.000 . Uani d ? O(1) 0.2298(1) 0.5573(2) 0.2846(2) 0.0793(9) 1.000 . Uani d ? O(2) 0.17907(9) 0.2878(1) -0.0094(2) 0.0554(6) 1.000 . Uani d ? O(3) 0.3684(1) 0.3029(2) -0.0452(2) 0.0712(8) 1.000 . Uani d ? C(1) 0.2219(1) 0.4952(2) 0.2187(2) 0.0493(9) 1.000 . Uani d ? C(2) 0.1666(1) 0.4961(2) 0.1473(2) 0.0472(9) 1.000 . Uani d ? C(3) 0.1637(1) 0.4383(2) 0.0589(2) 0.0480(9) 1.000 . Uani d ? C(4) 0.2093(1) 0.3690(2) 0.0295(2) 0.0435(9) 1.000 . Uani d ? C(5) 0.2470(1) 0.3398(2) 0.1338(2) 0.0439(8) 1.000 . Uani d ? C(6) 0.2982(1) 0.2752(2) 0.1034(2) 0.0476(9) 1.000 . Uani d ? C(7) 0.3512(1) 0.3230(2) 0.0487(2) 0.0481(9) 1.000 . Uani d ? C(8) 0.3811(1) 0.4014(2) 0.1165(2) 0.0426(8) 1.000 . Uani d ? C(9) 0.4204(1) 0.4627(2) 0.0411(3) 0.062(1) 1.000 . Uani d ? C(10) 0.3857(2) 0.5468(3) 0.0197(3) 0.083(1) 1.000 . Uani d ? C(11) 0.3218(2) 0.5316(2) 0.0603(3) 0.059(1) 1.000 . Uani d ? C(12) 0.3291(1) 0.4640(2) 0.1597(2) 0.0438(8) 1.000 . Uani d ? C(13) 0.2701(1) 0.4212(2) 0.2062(2) 0.0426(8) 1.000 . Uani d ? C(14) 0.1171(1) 0.5622(2) 0.1753(3) 0.071(1) 1.000 . Uani d ? C(15) 0.1563(2) 0.2953(3) -0.1185(3) 0.082(1) 1.000 . Uani d ? C(16) 0.4204(1) 0.3567(2) 0.2131(2) 0.0426(8) 1.000 . Uani d ? C(17) 0.2799(1) 0.3831(2) 0.3289(2) 0.053(1) 1.000 . Uani d ? C(18) 0.4875(2) 0.3677(2) 0.4081(3) 0.061(1) 1.000 . Uani d ? C(19) 0.5328(2) 0.3018(2) 0.3633(3) 0.068(1) 1.000 . Uani d ? C(20) 0.5048(1) 0.2297(2) 0.2836(3) 0.061(1) 1.000 . Uani d ? H(1) 0.1239 0.4381 0.0125 0.058 1.000 . Uiso c ? H(2) 0.2317 0.3870 -0.0359 0.052 1.000 . Uiso c ? H(3) 0.2205 0.3027 0.1696 0.053 1.000 . Uiso c ? H(4) 0.3091 0.2360 0.1685 0.057 1.000 . Uiso c ? H(5) 0.2808 0.2271 0.0455 0.057 1.000 . Uiso c ? H(6) 0.4611 0.4669 0.0461 0.074 1.000 . Uiso c ? H(7) 0.4316 0.4087 -0.0275 0.074 1.000 . Uiso c ? H(8) 0.4032 0.5937 0.0715 0.100 1.000 . Uiso c ? H(9) 0.3923 0.5944 -0.0452 0.100 1.000 . Uiso c ? H(10) 0.3008 0.5892 0.0859 0.071 1.000 . Uiso c ? H(11) 0.2983 0.5122 0.0044 0.071 1.000 . Uiso c ? H(12) 0.3452 0.5010 0.2142 0.053 1.000 . Uiso c ? H(13) 0.1140 0.5682 0.2542 0.085 1.000 . Uiso c ? H(14) 0.1271 0.6196 0.1426 0.085 1.000 . Uiso c ? H(15) 0.0794 0.5414 0.1448 0.085 1.000 . Uiso c ? H(16) 0.1141 0.3104 -0.1152 0.098 1.000 . Uiso c ? H(17) 0.1783 0.3417 -0.1569 0.098 1.000 . Uiso c ? H(18) 0.1618 0.2393 -0.1561 0.098 1.000 . Uiso c ? H(19) 0.3928 0.3251 0.2511 0.052 1.000 . Uiso c ? H(20) 0.2676 0.4277 0.3827 0.064 1.000 . Uiso c ? H(21) 0.2558 0.3299 0.3392 0.064 1.000 . Uiso c ? H(22) 0.3220 0.3689 0.3401 0.064 1.000 . Uiso c ? H(23) 0.5100 0.4044 0.4620 0.072 1.000 . Uiso c ? H(24) 0.4498 0.3403 0.4429 0.072 1.000 . Uiso c ? H(25) 0.5674 0.3310 0.3380 0.081 1.000 . Uiso c ? H(26) 0.5539 0.2632 0.4168 0.081 1.000 . Uiso c ? H(27) 0.4633 0.1935 0.3039 0.073 1.000 . Uiso c ? H(28) 0.5337 0.1847 0.2677 0.073 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 S(1) 0.0719(6) 0.0572(5) 0.0555(5) -0.0021(4) -0.0174(4) -0.0088(4) S(2) 0.0586(5) 0.0673(6) 0.0453(4) 0.0098(4) -0.0003(4) -0.0052(4) O(1) 0.104(2) 0.079(2) 0.055(1) 0.020(2) -0.020(1) -0.035(1) O(2) 0.062(1) 0.064(1) 0.041(1) -0.013(1) -0.010(1) -0.006(1) O(3) 0.074(2) 0.100(2) 0.039(1) 0.002(1) 0.002(1) -0.024(1) C(1) 0.055(2) 0.053(2) 0.040(2) 0.002(2) 0.000(2) 0.001(2) C(2) 0.041(2) 0.045(2) 0.055(2) 0.000(1) 0.003(2) 0.010(2) C(3) 0.049(2) 0.049(2) 0.046(2) -0.006(2) -0.004(1) 0.009(2) C(4) 0.048(2) 0.048(2) 0.034(2) -0.006(1) -0.002(1) 0.004(1) C(5) 0.050(2) 0.051(2) 0.031(1) -0.010(1) -0.002(1) 0.008(1) C(6) 0.048(2) 0.050(2) 0.044(2) 0.001(1) -0.003(1) -0.004(1) C(7) 0.048(2) 0.058(2) 0.039(2) 0.013(2) -0.011(1) -0.009(2) C(8) 0.051(2) 0.046(2) 0.031(1) -0.004(1) -0.000(1) 0.003(1) C(9) 0.062(2) 0.074(2) 0.051(2) -0.009(2) 0.010(2) 0.008(2) C(10) 0.073(3) 0.076(3) 0.100(3) -0.011(2) 0.000(2) 0.034(2) C(11) 0.073(2) 0.049(2) 0.056(2) -0.007(2) -0.012(2) 0.011(2) C(12) 0.053(2) 0.043(2) 0.035(2) -0.004(1) -0.009(1) -0.006(1) C(13) 0.049(2) 0.051(2) 0.027(1) 0.004(1) -0.005(1) -0.005(1) C(14) 0.056(2) 0.068(2) 0.088(3) 0.005(2) -0.002(2) -0.003(2) C(15) 0.095(3) 0.094(3) 0.056(2) -0.006(2) -0.024(2) -0.025(2) C(16) 0.044(2) 0.047(2) 0.037(2) -0.005(1) -0.006(1) 0.005(1) C(17) 0.055(2) 0.067(2) 0.036(2) -0.000(2) -0.002(1) -0.004(2) C(18) 0.072(2) 0.064(2) 0.046(2) 0.011(2) -0.009(2) -0.014(2) C(19) 0.058(2) 0.086(3) 0.060(2) -0.002(2) -0.016(2) 0.016(2) C(20) 0.059(2) 0.060(2) 0.063(2) 0.013(2) -0.005(2) 0.012(2) #============================================================================== # REFINEMENT DATA _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) + 0.00001|Fo|^2^]' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 2257 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.1125 _refine_ls_R_factor_gt 0.0940 _refine_ls_wR_factor_all 0.0920 _refine_ls_wR_factor_ref 0.0920 _refine_ls_goodness_of_fit_all 6.141 _refine_ls_goodness_of_fit_ref 6.930 _refine_ls_shift/su_max 0.0000 _refine_ls_shift/su_mean 0.0000 _refine_diff_density_min -0.42 _refine_diff_density_max 0.84 #============================================================================== # MOLECULAR GEOMETRY _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 S(1) C(16) 1.817(7) . . ? S(1) C(18) 1.825(8) . . ? S(2) C(16) 1.796(7) . . ? S(2) C(20) 1.820(8) . . ? O(1) C(1) 1.215(9) . . ? O(2) C(4) 1.441(8) . . ? O(2) C(15) 1.390(9) . . ? O(3) C(7) 1.212(8) . . ? C(1) C(2) 1.47(1) . . ? C(1) C(13) 1.52(1) . . ? C(2) C(3) 1.35(1) . . ? C(2) C(14) 1.49(1) . . ? C(3) C(4) 1.47(1) . . ? C(3) H(1) 1.03 . . no C(4) C(5) 1.545(9) . . ? C(4) H(2) 0.95 . . no C(5) C(6) 1.51(1) . . ? C(5) C(13) 1.559(9) . . ? C(5) H(3) 0.90 . . no C(6) C(7) 1.50(1) . . ? C(6) H(4) 0.99 . . no C(6) H(5) 1.06 . . no C(7) C(8) 1.55(1) . . ? C(8) C(9) 1.53(1) . . ? C(8) C(12) 1.55(1) . . ? C(8) C(16) 1.575(9) . . ? C(9) C(10) 1.47(1) . . ? C(9) H(6) 0.89 . . no C(9) H(7) 1.16 . . no C(10) C(11) 1.49(1) . . ? C(10) H(8) 1.00 . . no C(10) H(9) 1.05 . . no C(11) C(12) 1.55(1) . . ? C(11) H(10) 1.01 . . no C(11) H(11) 0.89 . . no C(12) C(13) 1.53(1) . . ? C(12) H(12) 0.92 . . no C(13) C(17) 1.574(9) . . ? C(14) H(13) 0.94 . . no C(14) H(14) 0.96 . . no C(14) H(15) 0.95 . . no C(15) H(16) 0.94 . . no C(15) H(17) 0.95 . . no C(15) H(18) 0.95 . . no C(16) H(19) 0.88 . . no C(17) H(20) 0.95 . . no C(17) H(21) 0.95 . . no C(17) H(22) 0.95 . . no C(18) C(19) 1.48(1) . . ? C(18) H(23) 0.97 . . no C(18) H(24) 1.00 . . no C(19) C(20) 1.55(1) . . ? C(19) H(25) 0.92 . . no C(19) H(26) 0.97 . . no C(20) H(27) 1.08 . . no C(20) H(28) 0.93 . . 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(16) S(1) C(18) 97.5(3) . . . ? C(16) S(2) C(20) 99.1(3) . . . ? C(4) O(2) C(15) 113.2(6) . . . ? O(1) C(1) C(2) 118.5(8) . . . ? O(1) C(1) C(13) 120.3(7) . . . ? C(2) C(1) C(13) 121.0(7) . . . ? C(1) C(2) C(3) 118.6(7) . . . ? C(1) C(2) C(14) 118.0(7) . . . ? C(3) C(2) C(14) 123.4(8) . . . ? C(2) C(3) C(4) 126.3(7) . . . ? C(2) C(3) H(1) 117.3 . . . no C(4) C(3) H(1) 116.1 . . . no O(2) C(4) C(3) 110.2(6) . . . ? O(2) C(4) C(5) 105.5(6) . . . ? O(2) C(4) H(2) 101.9 . . . no C(3) C(4) C(5) 111.3(6) . . . ? C(3) C(4) H(2) 110.2 . . . no C(5) C(4) H(2) 117.1 . . . no C(4) C(5) C(6) 112.1(6) . . . ? C(4) C(5) C(13) 113.5(6) . . . ? C(4) C(5) H(3) 101.9 . . . no C(6) C(5) C(13) 112.2(6) . . . ? C(6) C(5) H(3) 101.8 . . . no C(13) C(5) H(3) 114.4 . . . no C(5) C(6) C(7) 112.1(6) . . . ? C(5) C(6) H(4) 110.9 . . . no C(5) C(6) H(5) 108.2 . . . no C(7) C(6) H(4) 115.2 . . . no C(7) C(6) H(5) 108.1 . . . no H(4) C(6) H(5) 101.6 . . . no O(3) C(7) C(6) 121.4(7) . . . ? O(3) C(7) C(8) 121.9(8) . . . ? C(6) C(7) C(8) 116.6(6) . . . ? C(7) C(8) C(9) 111.7(6) . . . ? C(7) C(8) C(12) 108.0(6) . . . ? C(7) C(8) C(16) 107.1(6) . . . ? C(9) C(8) C(12) 104.5(6) . . . ? C(9) C(8) C(16) 111.5(6) . . . ? C(12) C(8) C(16) 114.0(6) . . . ? C(8) C(9) C(10) 108.0(7) . . . ? C(8) C(9) H(6) 123.9 . . . no C(8) C(9) H(7) 97.0 . . . no C(10) C(9) H(6) 117.7 . . . no C(10) C(9) H(7) 124.2 . . . no H(6) C(9) H(7) 83.3 . . . no C(9) C(10) C(11) 107.4(7) . . . ? C(9) C(10) H(8) 106.2 . . . no C(9) C(10) H(9) 128.1 . . . no C(11) C(10) H(8) 105.2 . . . no C(11) C(10) H(9) 117.7 . . . no H(8) C(10) H(9) 86.3 . . . no C(10) C(11) C(12) 104.2(7) . . . ? C(10) C(11) H(10) 113.2 . . . no C(10) C(11) H(11) 110.3 . . . no C(12) C(11) H(10) 110.9 . . . no C(12) C(11) H(11) 114.9 . . . no H(10) C(11) H(11) 103.6 . . . no C(8) C(12) C(11) 101.9(6) . . . ? C(8) C(12) C(13) 119.2(6) . . . ? C(8) C(12) H(12) 107.9 . . . no C(11) C(12) C(13) 116.9(6) . . . ? C(11) C(12) H(12) 101.2 . . . no C(13) C(12) H(12) 108.1 . . . no C(1) C(13) C(5) 112.4(6) . . . ? C(1) C(13) C(12) 108.6(6) . . . ? C(1) C(13) C(17) 105.0(6) . . . ? C(5) C(13) C(12) 112.9(6) . . . ? C(5) C(13) C(17) 106.2(6) . . . ? C(12) C(13) C(17) 111.5(6) . . . ? C(2) C(14) H(13) 109.5 . . . no C(2) C(14) H(14) 108.9 . . . no C(2) C(14) H(15) 109.3 . . . no H(13) C(14) H(14) 109.7 . . . no H(13) C(14) H(15) 110.3 . . . no H(14) C(14) H(15) 109.1 . . . no O(2) C(15) H(16) 109.1 . . . no O(2) C(15) H(17) 108.9 . . . no O(2) C(15) H(18) 108.8 . . . no H(16) C(15) H(17) 109.9 . . . no H(16) C(15) H(18) 110.3 . . . no H(17) C(15) H(18) 109.8 . . . no S(1) C(16) S(2) 112.8(4) . . . ? S(1) C(16) C(8) 110.6(5) . . . ? S(1) C(16) H(19) 110.6 . . . no S(2) C(16) C(8) 110.2(5) . . . ? S(2) C(16) H(19) 109.4 . . . no C(8) C(16) H(19) 102.8 . . . no C(13) C(17) H(20) 109.5 . . . no C(13) C(17) H(21) 109.8 . . . no C(13) C(17) H(22) 109.8 . . . no H(20) C(17) H(21) 109.0 . . . no H(20) C(17) H(22) 109.2 . . . no H(21) C(17) H(22) 109.5 . . . no S(1) C(18) C(19) 114.5(6) . . . ? S(1) C(18) H(23) 108.1 . . . no S(1) C(18) H(24) 102.0 . . . no C(19) C(18) H(23) 105.4 . . . no C(19) C(18) H(24) 115.4 . . . no H(23) C(18) H(24) 111.5 . . . no C(18) C(19) C(20) 114.0(7) . . . ? C(18) C(19) H(25) 110.9 . . . no C(18) C(19) H(26) 117.8 . . . no C(20) C(19) H(25) 116.4 . . . no C(20) C(19) H(26) 100.6 . . . no H(25) C(19) H(26) 95.8 . . . no S(2) C(20) C(19) 111.5(6) . . . ? S(2) C(20) H(27) 96.2 . . . no S(2) C(20) H(28) 110.6 . . . no C(19) C(20) H(27) 122.3 . . . no C(19) C(20) H(28) 110.2 . . . no H(27) C(20) H(28) 105.1 . . . 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) 3.372(9) . 4_565 no O(1) C(15) 3.49(1) . 4_565 no O(1) O(3) 3.589(8) . 4_565 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 S(1) C(16) S(2) C(20) . . . . 63.9(4) no S(1) C(16) C(8) C(7) . . . . -177.3(5) no S(1) C(16) C(8) C(9) . . . . 60.2(7) no S(1) C(16) C(8) C(12) . . . . -57.9(7) no S(1) C(18) C(19) C(20) . . . . -67.1(9) no S(2) C(16) S(1) C(18) . . . . -62.1(5) no S(2) C(16) C(8) C(7) . . . . 57.4(7) no S(2) C(16) C(8) C(9) . . . . -65.1(7) no S(2) C(16) C(8) C(12) . . . . 176.8(5) no S(2) C(20) C(19) C(18) . . . . 66.2(9) no O(1) C(1) C(2) C(3) . . . . 166.7(7) no O(1) C(1) C(2) C(14) . . . . -12(1) no O(1) C(1) C(13) C(5) . . . . 170.3(7) no O(1) C(1) C(13) C(12) . . . . -64.1(9) no O(1) C(1) C(13) C(17) . . . . 55.3(9) no O(2) C(4) C(3) C(2) . . . . 141.0(7) no O(2) C(4) C(5) C(6) . . . . 66.0(8) no O(2) C(4) C(5) C(13) . . . . -165.6(6) no O(3) C(7) C(6) C(5) . . . . -120.9(8) no O(3) C(7) C(8) C(9) . . . . 15(1) no O(3) C(7) C(8) C(12) . . . . 129.4(8) no O(3) C(7) C(8) C(16) . . . . -107.4(8) no C(1) C(2) C(3) C(4) . . . . 4(1) no C(1) C(13) C(5) C(4) . . . . 40.9(8) no C(1) C(13) C(5) C(6) . . . . 169.3(6) no C(1) C(13) C(12) C(8) . . . . -167.9(6) no C(1) C(13) C(12) C(11) . . . . -44.7(8) no C(2) C(1) C(13) C(5) . . . . -13(1) no C(2) C(1) C(13) C(12) . . . . 112.4(7) no C(2) C(1) C(13) C(17) . . . . -128.2(7) no C(2) C(3) C(4) C(5) . . . . 24(1) no C(3) C(2) C(1) C(13) . . . . -10(1) no C(3) C(4) O(2) C(15) . . . . 75.8(8) no C(3) C(4) C(5) C(6) . . . . -174.5(6) no C(3) C(4) C(5) C(13) . . . . -46.0(8) no C(4) C(3) C(2) C(14) . . . . -177.1(7) no C(4) C(5) C(6) C(7) . . . . 75.8(8) no C(4) C(5) C(13) C(12) . . . . -82.3(8) no C(4) C(5) C(13) C(17) . . . . 155.2(6) no C(5) C(4) O(2) C(15) . . . . -164.0(7) no C(5) C(6) C(7) C(8) . . . . 57.0(8) no C(5) C(13) C(12) C(8) . . . . -42.5(9) no C(5) C(13) C(12) C(11) . . . . 80.7(8) no C(6) C(5) C(13) C(12) . . . . 46.1(8) no C(6) C(5) C(13) C(17) . . . . -76.4(7) no C(6) C(7) C(8) C(9) . . . . -162.8(7) no C(6) C(7) C(8) C(12) . . . . -48.4(8) no C(6) C(7) C(8) C(16) . . . . 74.8(8) no C(7) C(6) C(5) C(13) . . . . -53.3(8) no C(7) C(8) C(9) C(10) . . . . 103.5(8) no C(7) C(8) C(12) C(11) . . . . -88.6(7) no C(7) C(8) C(12) C(13) . . . . 41.6(8) no C(8) C(9) C(10) C(11) . . . . -11(1) no C(8) C(12) C(11) C(10) . . . . -37.5(8) no C(8) C(12) C(13) C(17) . . . . 76.9(8) no C(8) C(16) S(1) C(18) . . . . 174.1(5) no C(8) C(16) S(2) C(20) . . . . -172.0(5) no C(9) C(8) C(12) C(11) . . . . 30.5(7) no C(9) C(8) C(12) C(13) . . . . 160.7(6) no C(9) C(10) C(11) C(12) . . . . 31(1) no C(10) C(9) C(8) C(12) . . . . -13.0(9) no C(10) C(9) C(8) C(16) . . . . -136.6(7) no C(10) C(11) C(12) C(13) . . . . -169.2(7) no C(11) C(12) C(8) C(16) . . . . 152.5(6) no C(11) C(12) C(13) C(17) . . . . -159.9(6) no C(13) C(1) C(2) C(14) . . . . 171.1(7) no C(13) C(12) C(8) C(16) . . . . -77.2(8) no C(16) S(1) C(18) C(19) . . . . 60.1(7) no C(16) S(2) C(20) C(19) . . . . -60.2(7) no #------------------------------------------------------------------------------ #============================================================================== data_cl-ii-3 _database_code_CSD 164941 #============================================================================== _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan for Windows version 1.06 (MSC, 1997-1999)' _computing_structure_solution ? _computing_structure_refinement 'teXsan for Windows version 1.06 (MSC, 1997-1999)' _computing_publication_material 'teXsan for Windows version 1.06 (MSC, 1997-1999)' #------------------------------------------------------------------------------ _cell_length_a 9.055(3) _cell_length_b 9.055(3) _cell_length_c 18.635(6) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1527.8(7) _cell_formula_units_Z 4 _cell_measurement_temperature 299.2 _cell_measurement_reflns_used 22 _cell_measurement_theta_min 10.1 _cell_measurement_theta_max 13.4 #------------------------------------------------------------------------------ _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M 'P 43 ' _symmetry_Int_Tables_number 78 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x, -y,1/2+z' ' -y, +x,3/4+z' ' +y, -x,1/4+z' #------------------------------------------------------------------------------ _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _exptl_crystal_description 'irreg.' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.375 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 316.35 _chemical_formula_analytical ? _chemical_formula_sum 'C18 H20 O5 ' _chemical_formula_moiety 'C18 H20 O5 ' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 672.00 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type none _exptl_special_details ; The scan width was (1.10+0.35tan\q)\% with an \w scan speed of 4\% per minute (up to 6 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. ; #============================================================================== # EXPERIMENTAL DATA _diffrn_special_details ; ? ; _diffrn_ambient_temperature 299.2 _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 'Rigaku AFC6S' _diffrn_measurement_method \w-2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 0.03 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 1 1 3 2 0 1 2 0 -1 _diffrn_reflns_number 1588 _reflns_number_total 1409 _reflns_number_gt 1045 _reflns_threshold_expression I>1.50\s(I) _diffrn_reflns_av_R_equivalents 0.02250 _diffrn_reflns_av_sigmaI/netI 0.064 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 25.06 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 0.04590 _diffrn_orient_matrix_UB_12 0.08833 _diffrn_orient_matrix_UB_13 -0.02324 _diffrn_orient_matrix_UB_21 -0.06395 _diffrn_orient_matrix_UB_22 0.06625 _diffrn_orient_matrix_UB_23 0.02963 _diffrn_orient_matrix_UB_31 0.07746 _diffrn_orient_matrix_UB_32 0.00236 _diffrn_orient_matrix_UB_33 0.03823 #------------------------------------------------------------------------------ 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 72 0.002 0.002 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; H 0 80 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; O 0 20 0.008 0.006 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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) 0.4920(3) 0.2335(3) 0.7043 0.0469(7) 1.000 . Uani d ? O(2) 0.4787(3) 0.1433(3) 0.8150(2) 0.0573(8) 1.000 . Uani d ? O(3) 0.2310(3) -0.3004(3) 0.5740(2) 0.082(1) 1.000 . Uani d ? O(4) 0.6221(3) 0.0423(3) 0.4320(2) 0.0555(8) 1.000 . Uani d ? O(5) 0.8382(2) 0.0783(3) 0.5824(2) 0.0533(8) 1.000 . Uani d ? C(1) 0.4368(4) 0.1382(4) 0.7534(2) 0.044(1) 1.000 . Uani d ? C(2) 0.3262(4) 0.0365(4) 0.7205(2) 0.041(1) 1.000 . Uani d ? C(3) 0.3636(3) 0.0483(4) 0.6409(2) 0.0367(9) 1.000 . Uani d ? C(4) 0.4956(3) -0.0458(3) 0.6151(2) 0.0328(9) 1.000 . Uani d ? C(5) 0.4761(3) -0.1998(4) 0.5758(2) 0.039(1) 1.000 . Uani d ? C(6) 0.3185(4) -0.2118(4) 0.5491(2) 0.048(1) 1.000 . Uani d ? C(7) 0.2719(4) -0.1041(4) 0.4936(2) 0.049(1) 1.000 . Uani d ? C(8) 0.3737(4) -0.0148(4) 0.4658(2) 0.048(1) 1.000 . Uani d ? C(9) 0.5320(4) -0.0213(4) 0.4862(2) 0.0368(9) 1.000 . Uani d ? C(10) 0.5789(4) -0.1767(4) 0.5098(2) 0.042(1) 1.000 . Uani d ? C(11) 0.7406(4) -0.1512(4) 0.5327(2) 0.049(1) 1.000 . Uani d ? C(12) 0.7366(4) 0.0065(4) 0.5613(2) 0.039(1) 1.000 . Uani d ? C(13) 0.5758(3) 0.0527(3) 0.5587(2) 0.0338(9) 1.000 . Uani d ? C(14) 0.5365(4) 0.2130(4) 0.5751(2) 0.046(1) 1.000 . Uani d ? C(15) 0.4212(4) 0.2064(4) 0.6342(2) 0.042(1) 1.000 . Uani d ? C(16) 0.3193(4) -0.1144(5) 0.7554(2) 0.059(1) 1.000 . Uani d ? C(17) 0.5168(5) -0.3334(4) 0.6221(3) 0.064(1) 1.000 . Uani d ? C(18) 0.1101(4) -0.0992(5) 0.4752(3) 0.080(2) 1.000 . Uani d ? H(1) 0.2340 0.1010 0.7265 0.049 1.000 . Uiso c ? H(2) 0.2748 0.0378 0.6123 0.044 1.000 . Uiso c ? H(3) 0.5617 -0.0575 0.6595 0.037 1.000 . Uiso c ? H(4) 0.3524 0.0671 0.4219 0.058 1.000 . Uiso c ? H(5) 0.5658 -0.2573 0.4718 0.046 1.000 . Uiso c ? H(6) 0.7807 -0.2228 0.5694 0.058 1.000 . Uiso c ? H(7) 0.8085 -0.1512 0.4891 0.058 1.000 . Uiso c ? H(8) 0.6254 0.2677 0.5952 0.053 1.000 . Uiso c ? H(9) 0.4910 0.2518 0.5327 0.053 1.000 . Uiso c ? H(10) 0.3393 0.2826 0.6252 0.047 1.000 . Uiso c ? H(11) 0.2783 -0.1105 0.8038 0.068 1.000 . Uiso c ? H(12) 0.2656 -0.1860 0.7274 0.068 1.000 . Uiso c ? H(13) 0.4183 -0.1516 0.7609 0.068 1.000 . Uiso c ? H(14) 0.4379 -0.3453 0.6625 0.075 1.000 . Uiso c ? H(15) 0.5317 -0.4201 0.5869 0.075 1.000 . Uiso c ? H(16) 0.6189 -0.3159 0.6426 0.075 1.000 . Uiso c ? H(17) 0.0667 -0.0564 0.5204 0.092 1.000 . Uiso c ? H(18) 0.0931 -0.0465 0.4394 0.092 1.000 . Uiso c ? H(19) 0.0721 -0.2091 0.4661 0.092 1.000 . Uiso c ? H(20) 0.6269 0.0035 0.3850 0.067 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) 0.055(2) 0.050(1) 0.035(1) -0.009(1) -0.002(1) -0.006(1) O(2) 0.064(2) 0.076(2) 0.031(1) -0.012(1) -0.006(1) -0.006(1) O(3) 0.067(2) 0.095(2) 0.084(2) -0.044(2) 0.015(2) -0.008(2) O(4) 0.066(2) 0.072(2) 0.028(1) -0.010(1) 0.013(1) 0.001(1) O(5) 0.041(1) 0.066(2) 0.053(2) -0.017(1) -0.002(1) 0.003(1) C(1) 0.046(2) 0.053(2) 0.033(2) 0.000(2) 0.006(2) -0.008(2) C(2) 0.041(2) 0.054(2) 0.028(2) -0.002(2) 0.006(2) -0.009(2) C(3) 0.032(2) 0.049(2) 0.029(2) -0.001(2) -0.000(1) -0.006(2) C(4) 0.033(2) 0.039(2) 0.027(2) -0.004(1) 0.000(1) 0.002(1) C(5) 0.042(2) 0.037(2) 0.040(2) -0.000(2) 0.006(2) -0.002(2) C(6) 0.046(2) 0.055(2) 0.044(2) -0.009(2) 0.014(2) -0.022(2) C(7) 0.037(2) 0.065(3) 0.045(2) -0.000(2) 0.001(2) -0.027(2) C(8) 0.056(2) 0.057(2) 0.032(2) 0.008(2) -0.007(2) -0.012(2) C(9) 0.039(2) 0.045(2) 0.027(2) -0.001(2) 0.006(1) -0.003(1) C(10) 0.037(2) 0.047(2) 0.041(2) 0.003(2) 0.005(2) -0.008(2) C(11) 0.033(2) 0.060(2) 0.055(2) 0.005(2) 0.005(2) -0.004(2) C(12) 0.034(2) 0.053(2) 0.030(2) -0.006(2) 0.005(2) 0.009(2) C(13) 0.035(2) 0.040(2) 0.026(2) -0.003(1) 0.004(1) 0.001(1) C(14) 0.057(2) 0.043(2) 0.037(2) -0.004(2) -0.000(2) 0.004(2) C(15) 0.047(2) 0.044(2) 0.033(2) 0.007(2) -0.007(2) -0.004(2) C(16) 0.069(3) 0.072(3) 0.037(2) -0.029(2) 0.008(2) 0.000(2) C(17) 0.083(3) 0.040(2) 0.069(3) -0.001(2) 0.014(2) 0.006(2) C(18) 0.045(2) 0.114(4) 0.081(3) 0.008(2) -0.017(2) -0.049(3) #============================================================================== # REFINEMENT DATA _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) + 0.00008|Fo|^2^]' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method 'Zachariasen (1967)' _refine_ls_extinction_coef 0.0000011(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 1045 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.0678 _refine_ls_R_factor_gt 0.0330 _refine_ls_wR_factor_all 0.0370 _refine_ls_wR_factor_ref 0.0330 _refine_ls_goodness_of_fit_all 1.285 _refine_ls_goodness_of_fit_ref 1.360 _refine_ls_shift/su_max 0.0000 _refine_ls_shift/su_mean 0.0000 _refine_diff_density_min -0.11 _refine_diff_density_max 0.12 #============================================================================== # MOLECULAR GEOMETRY _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(1) 1.354(5) . . ? O(1) C(15) 1.476(4) . . ? O(2) C(1) 1.210(5) . . ? O(3) C(6) 1.219(5) . . ? O(4) C(9) 1.421(4) . . ? O(4) H(20) 0.94 . . no O(5) C(12) 1.192(4) . . ? C(1) C(2) 1.492(5) . . ? C(2) C(3) 1.525(5) . . ? C(2) C(16) 1.514(6) . . ? C(2) H(1) 1.02 . . no C(3) C(4) 1.544(5) . . ? C(3) C(15) 1.529(5) . . ? C(3) H(2) 0.97 . . no C(4) C(5) 1.584(5) . . ? C(4) C(13) 1.559(5) . . ? C(4) H(3) 1.03 . . no C(5) C(6) 1.515(5) . . ? C(5) C(10) 1.557(5) . . ? C(5) C(17) 1.530(6) . . ? C(6) C(7) 1.482(6) . . ? C(7) C(8) 1.332(6) . . ? C(7) C(18) 1.505(6) . . ? C(8) C(9) 1.484(5) . . ? C(8) H(4) 1.12 . . no C(9) C(10) 1.535(5) . . ? C(9) C(13) 1.558(5) . . ? C(10) C(11) 1.543(5) . . ? C(10) H(5) 1.02 . . no C(11) C(12) 1.525(6) . . ? C(11) H(6) 1.01 . . no C(11) H(7) 1.02 . . no C(12) C(13) 1.516(5) . . ? C(13) C(14) 1.526(5) . . ? C(14) C(15) 1.520(5) . . ? C(14) H(8) 1.02 . . no C(14) H(9) 0.96 . . no C(15) H(10) 1.03 . . no C(16) H(11) 0.98 . . no C(16) H(12) 0.96 . . no C(16) H(13) 0.96 . . no C(17) H(14) 1.04 . . no C(17) H(15) 1.03 . . no C(17) H(16) 1.01 . . no C(18) H(17) 1.01 . . no C(18) H(18) 0.83 . . no C(18) H(19) 1.07 . . 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(1) O(1) C(15) 109.4(3) . . . ? C(9) O(4) H(20) 122.4 . . . no O(1) C(1) O(2) 120.0(4) . . . ? O(1) C(1) C(2) 111.3(3) . . . ? O(2) C(1) C(2) 128.6(4) . . . ? C(1) C(2) C(3) 102.0(3) . . . ? C(1) C(2) C(16) 114.1(3) . . . ? C(1) C(2) H(1) 98.6 . . . no C(3) C(2) C(16) 119.3(3) . . . ? C(3) C(2) H(1) 104.3 . . . no C(16) C(2) H(1) 115.7 . . . no C(2) C(3) C(4) 115.9(3) . . . ? C(2) C(3) C(15) 102.7(3) . . . ? C(2) C(3) H(2) 110.2 . . . no C(4) C(3) C(15) 103.2(3) . . . ? C(4) C(3) H(2) 114.6 . . . no C(15) C(3) H(2) 109.2 . . . no C(3) C(4) C(5) 122.9(3) . . . ? C(3) C(4) C(13) 104.8(3) . . . ? C(3) C(4) H(3) 104.9 . . . no C(5) C(4) C(13) 104.1(3) . . . ? C(5) C(4) H(3) 110.3 . . . no C(13) C(4) H(3) 109.4 . . . no C(4) C(5) C(6) 108.7(3) . . . ? C(4) C(5) C(10) 100.4(3) . . . ? C(4) C(5) C(17) 114.1(3) . . . ? C(6) C(5) C(10) 108.2(3) . . . ? C(6) C(5) C(17) 110.8(4) . . . ? C(10) C(5) C(17) 114.0(3) . . . ? O(3) C(6) C(5) 122.2(4) . . . ? O(3) C(6) C(7) 120.9(4) . . . ? C(5) C(6) C(7) 116.8(4) . . . ? C(6) C(7) C(8) 118.3(4) . . . ? C(6) C(7) C(18) 117.1(4) . . . ? C(8) C(7) C(18) 124.6(5) . . . ? C(7) C(8) C(9) 123.0(4) . . . ? C(7) C(8) H(4) 124.5 . . . no C(9) C(8) H(4) 112.3 . . . no O(4) C(9) C(8) 110.9(3) . . . ? O(4) C(9) C(10) 114.6(3) . . . ? O(4) C(9) C(13) 107.2(3) . . . ? C(8) C(9) C(10) 112.1(3) . . . ? C(8) C(9) C(13) 116.8(3) . . . ? C(10) C(9) C(13) 94.3(3) . . . ? C(5) C(10) C(9) 100.6(3) . . . ? C(5) C(10) C(11) 111.7(3) . . . ? C(5) C(10) H(5) 112.5 . . . no C(9) C(10) C(11) 101.8(3) . . . ? C(9) C(10) H(5) 115.0 . . . no C(11) C(10) H(5) 114.1 . . . no C(10) C(11) C(12) 102.4(3) . . . ? C(10) C(11) H(6) 115.6 . . . no C(10) C(11) H(7) 110.6 . . . no C(12) C(11) H(6) 111.9 . . . no C(12) C(11) H(7) 107.1 . . . no H(6) C(11) H(7) 108.8 . . . no O(5) C(12) C(11) 127.4(4) . . . ? O(5) C(12) C(13) 127.0(4) . . . ? C(11) C(12) C(13) 105.6(3) . . . ? C(4) C(13) C(9) 102.7(3) . . . ? C(4) C(13) C(12) 105.5(3) . . . ? C(4) C(13) C(14) 107.5(3) . . . ? C(9) C(13) C(12) 98.9(3) . . . ? C(9) C(13) C(14) 121.5(3) . . . ? C(12) C(13) C(14) 118.7(3) . . . ? C(13) C(14) C(15) 105.6(3) . . . ? C(13) C(14) H(8) 110.6 . . . no C(13) C(14) H(9) 106.5 . . . no C(15) C(14) H(8) 107.2 . . . no C(15) C(14) H(9) 108.5 . . . no H(8) C(14) H(9) 117.8 . . . no O(1) C(15) C(3) 103.4(3) . . . ? O(1) C(15) C(14) 109.7(3) . . . ? O(1) C(15) H(10) 110.2 . . . no C(3) C(15) C(14) 109.3(3) . . . ? C(3) C(15) H(10) 113.4 . . . no C(14) C(15) H(10) 110.6 . . . no C(2) C(16) H(11) 112.3 . . . no C(2) C(16) H(12) 113.4 . . . no C(2) C(16) H(13) 108.9 . . . no H(11) C(16) H(12) 109.4 . . . no H(11) C(16) H(13) 105.5 . . . no H(12) C(16) H(13) 107.0 . . . no C(5) C(17) H(14) 108.8 . . . no C(5) C(17) H(15) 106.0 . . . no C(5) C(17) H(16) 108.0 . . . no H(14) C(17) H(15) 118.0 . . . no H(14) C(17) H(16) 111.6 . . . no H(15) C(17) H(16) 103.8 . . . no C(7) C(18) H(17) 101.5 . . . no C(7) C(18) H(18) 112.2 . . . no C(7) C(18) H(19) 108.8 . . . no H(17) C(18) H(18) 112.2 . . . no H(17) C(18) H(19) 111.5 . . . no H(18) C(18) H(19) 110.3 . . . 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(11) 3.554(5) . 4_665 no O(1) C(10) 3.599(5) . 4_665 no O(2) O(4) 2.901(4) . 2_655 no O(2) C(8) 3.322(5) . 2_655 no O(2) C(9) 3.378(5) . 2_655 no O(2) C(11) 3.563(5) . 4_665 no O(3) C(8) 3.518(5) . 4 no O(4) C(16) 3.398(5) . 2_654 no O(5) C(18) 3.211(6) . 4_655 no O(5) C(2) 3.267(4) . 3_654 no O(5) C(18) 3.554(6) . 1_655 no O(5) C(1) 3.570(5) . 3_654 no C(11) C(18) 3.544(6) . 1_655 no C(12) C(18) 3.556(6) . 4_655 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(1) C(2) C(3) . . . . 19.5(4) no O(1) C(1) C(2) C(16) . . . . 149.4(3) no O(1) C(15) C(3) C(2) . . . . 32.1(4) no O(1) C(15) C(3) C(4) . . . . -88.7(3) no O(1) C(15) C(14) C(13) . . . . 99.1(3) no O(2) C(1) O(1) C(15) . . . . -178.9(4) no O(2) C(1) C(2) C(3) . . . . -160.6(4) no O(2) C(1) C(2) C(16) . . . . -30.6(6) no O(3) C(6) C(5) C(4) . . . . -112.3(4) no O(3) C(6) C(5) C(10) . . . . 139.5(4) no O(3) C(6) C(5) C(17) . . . . 13.9(5) no O(3) C(6) C(7) C(8) . . . . -176.8(4) no O(3) C(6) C(7) C(18) . . . . 6.0(6) no O(4) C(9) C(8) C(7) . . . . 158.1(4) no O(4) C(9) C(10) C(5) . . . . 171.3(3) no O(4) C(9) C(10) C(11) . . . . 56.2(4) no O(4) C(9) C(13) C(4) . . . . -168.9(3) no O(4) C(9) C(13) C(12) . . . . -60.6(3) no O(4) C(9) C(13) C(14) . . . . 71.1(4) no O(5) C(12) C(11) C(10) . . . . -176.3(4) no O(5) C(12) C(13) C(4) . . . . -112.0(4) no O(5) C(12) C(13) C(9) . . . . 142.1(4) no O(5) C(12) C(13) C(14) . . . . 8.5(5) no C(1) O(1) C(15) C(3) . . . . -21.3(4) no C(1) O(1) C(15) C(14) . . . . -137.8(3) no C(1) C(2) C(3) C(4) . . . . 80.7(4) no C(1) C(2) C(3) C(15) . . . . -30.9(4) no C(2) C(1) O(1) C(15) . . . . 1.1(4) no C(2) C(3) C(4) C(5) . . . . 99.6(4) no C(2) C(3) C(4) C(13) . . . . -142.3(3) no C(2) C(3) C(15) C(14) . . . . 148.9(3) no C(3) C(4) C(5) C(6) . . . . 17.1(5) no C(3) C(4) C(5) C(10) . . . . 130.5(3) no C(3) C(4) C(5) C(17) . . . . -107.1(4) no C(3) C(4) C(13) C(9) . . . . -105.6(3) no C(3) C(4) C(13) C(12) . . . . 151.3(3) no C(3) C(4) C(13) C(14) . . . . 23.7(4) no C(3) C(15) C(14) C(13) . . . . -13.6(4) no C(4) C(3) C(2) C(16) . . . . -45.9(5) no C(4) C(3) C(15) C(14) . . . . 28.1(4) no C(4) C(5) C(6) C(7) . . . . 64.1(4) no C(4) C(5) C(10) C(9) . . . . -45.6(3) no C(4) C(5) C(10) C(11) . . . . 61.8(4) no C(4) C(13) C(9) C(8) . . . . 66.0(4) no C(4) C(13) C(9) C(10) . . . . -51.5(3) no C(4) C(13) C(12) C(11) . . . . 67.1(3) no C(4) C(13) C(14) C(15) . . . . -6.5(4) no C(5) C(4) C(3) C(15) . . . . -148.9(3) no C(5) C(4) C(13) C(9) . . . . 24.6(3) no C(5) C(4) C(13) C(12) . . . . -78.6(3) no C(5) C(4) C(13) C(14) . . . . 153.8(3) no C(5) C(6) C(7) C(8) . . . . 6.7(5) no C(5) C(6) C(7) C(18) . . . . -170.5(3) no C(5) C(10) C(9) C(8) . . . . -61.2(4) no C(5) C(10) C(9) C(13) . . . . 60.1(3) no C(5) C(10) C(11) C(12) . . . . -74.4(4) no C(6) C(5) C(4) C(13) . . . . -101.2(3) no C(6) C(5) C(10) C(9) . . . . 68.2(4) no C(6) C(5) C(10) C(11) . . . . 175.5(3) no C(6) C(7) C(8) C(9) . . . . 1.8(6) no C(7) C(6) C(5) C(10) . . . . -44.0(4) no C(7) C(6) C(5) C(17) . . . . -169.7(3) no C(7) C(8) C(9) C(10) . . . . 28.5(5) no C(7) C(8) C(9) C(13) . . . . -78.7(5) no C(8) C(9) C(10) C(11) . . . . -176.2(3) no C(8) C(9) C(13) C(12) . . . . 174.3(3) no C(8) C(9) C(13) C(14) . . . . -54.0(5) no C(9) C(8) C(7) C(18) . . . . 178.9(4) no C(9) C(10) C(5) C(17) . . . . -168.0(3) no C(9) C(10) C(11) C(12) . . . . 32.2(4) no C(9) C(13) C(12) C(11) . . . . -38.9(3) no C(9) C(13) C(14) C(15) . . . . 111.2(4) no C(10) C(5) C(4) C(13) . . . . 12.2(3) no C(10) C(9) C(13) C(12) . . . . 56.8(3) no C(10) C(9) C(13) C(14) . . . . -171.5(3) no C(10) C(11) C(12) C(13) . . . . 4.6(4) no C(11) C(10) C(5) C(17) . . . . -60.7(5) no C(11) C(10) C(9) C(13) . . . . -54.9(3) no C(11) C(12) C(13) C(14) . . . . -172.4(3) no C(12) C(13) C(14) C(15) . . . . -126.0(3) no C(13) C(4) C(3) C(15) . . . . -30.9(3) no C(13) C(4) C(5) C(17) . . . . 134.5(3) no C(15) C(3) C(2) C(16) . . . . -157.6(3) no #------------------------------------------------------------------------------ #============================================================================== data_cliv18p _database_code_CSD 164942 #============================================================================== _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan for Windows version 1.06 (MSC, 1997-1999)' _computing_structure_solution ; SIR92 (Altomare, et. al. 1994) ; _computing_structure_refinement 'teXsan for Windows version 1.06 (MSC, 1997-1999)' _computing_publication_material 'teXsan for Windows version 1.06 (MSC, 1997-1999)' #------------------------------------------------------------------------------ _cell_length_a 6.942(7) _cell_length_b 27.82(1) _cell_length_c 7.998(4) _cell_angle_alpha 90 _cell_angle_beta 94.95(7) _cell_angle_gamma 90 _cell_volume 1539(2) _cell_formula_units_Z 4 _cell_measurement_temperature 299.2 _cell_measurement_reflns_used 19 _cell_measurement_theta_min 9.7 _cell_measurement_theta_max 17.2 #------------------------------------------------------------------------------ _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' '1/2-x,1/2+y,1/2-z' ' -x, -y, -z' '1/2+x,1/2-y,1/2+z' #------------------------------------------------------------------------------ _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _exptl_crystal_description 'irregular' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.374 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 318.37 _chemical_formula_analytical ? _chemical_formula_sum 'C18 H22 O5 ' _chemical_formula_moiety 'C18 H22 O5 ' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 680.00 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type none _exptl_special_details ; The scan width was (1.26+0.35tan\q)\% with an \w scan speed of 4\% per minute (up to 5 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. ; #============================================================================== # EXPERIMENTAL DATA _diffrn_special_details ; ? ; _diffrn_ambient_temperature 299.2 _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 'Rigaku AFC6S' _diffrn_measurement_method \w-2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 0.22 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 0 0 2 0 -1 2 0 1 2 _diffrn_reflns_number 3045 _reflns_number_total 2809 _reflns_number_gt 1331 _reflns_threshold_expression I>2.00\s(I) _diffrn_reflns_av_R_equivalents 0.12140 _diffrn_reflns_av_sigmaI/netI 0.127 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 25.11 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 -0.00334 _diffrn_orient_matrix_UB_12 0.00909 _diffrn_orient_matrix_UB_13 0.12070 _diffrn_orient_matrix_UB_21 -0.03262 _diffrn_orient_matrix_UB_22 -0.03393 _diffrn_orient_matrix_UB_23 0.02771 _diffrn_orient_matrix_UB_31 0.14083 _diffrn_orient_matrix_UB_32 -0.00762 _diffrn_orient_matrix_UB_33 0.02039 #------------------------------------------------------------------------------ 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 72 0.002 0.002 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; H 0 88 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; O 0 20 0.008 0.006 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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) 0.3262(5) 0.0989(1) -0.3515(5) 0.063(1) 1.000 . Uani d ? O(2) 0.1940(6) 0.0515(1) -0.1679(5) 0.076(1) 1.000 . Uani d ? O(3) 0.6308(5) 0.1068(1) 0.2053(4) 0.048(1) 1.000 . Uani d ? O(4) 1.2593(5) 0.2002(1) 0.1296(5) 0.071(1) 1.000 . Uani d ? O(5) 0.9104(6) 0.1885(1) -0.4552(5) 0.082(2) 1.000 . Uani d ? C(1) 0.3408(8) 0.0670(2) -0.2176(7) 0.053(2) 1.000 . Uani d ? C(2) 0.5480(8) 0.0592(2) -0.1618(6) 0.045(2) 1.000 . Uani d ? C(3) 0.6536(7) 0.1024(2) -0.2284(5) 0.040(1) 1.000 . Uani d ? C(4) 0.6444(7) 0.1500(1) -0.1258(6) 0.041(1) 1.000 . Uani d ? C(5) 0.7988(6) 0.1579(1) 0.0221(5) 0.035(1) 1.000 . Uani d ? C(6) 0.7869(7) 0.1165(1) 0.1558(6) 0.037(1) 1.000 . Uani d ? C(7) 0.9724(7) 0.0929(2) 0.2138(6) 0.046(2) 1.000 . Uani d ? C(8) 1.1377(8) 0.1278(2) 0.2456(7) 0.057(2) 1.000 . Uani d ? C(9) 1.1460(7) 0.1667(2) 0.1137(6) 0.046(2) 1.000 . Uani d ? C(10) 1.0002(7) 0.1610(1) -0.0338(6) 0.040(1) 1.000 . Uani d ? C(11) 1.0196(8) 0.2000(2) -0.1706(7) 0.056(2) 1.000 . Uani d ? C(12) 0.8661(8) 0.1926(2) -0.3083(7) 0.053(2) 1.000 . Uani d ? C(13) 0.6599(8) 0.1881(1) -0.2708(6) 0.049(2) 1.000 . Uani d ? C(14) 0.5197(8) 0.1695(2) -0.4117(6) 0.057(2) 1.000 . Uani d ? C(15) 0.5192(8) 0.1137(2) -0.3851(6) 0.051(2) 1.000 . Uani d ? C(16) 0.6208(9) 0.0115(2) -0.2321(7) 0.070(2) 1.000 . Uani d ? C(17) 0.7417(7) 0.2041(2) 0.1160(6) 0.048(2) 1.000 . Uani d ? C(18) 0.9510(8) 0.0595(2) 0.3652(6) 0.059(2) 1.000 . Uani d ? H(1) 0.5596 0.0569 -0.0650 0.053 1.000 . Uiso c ? H(2) 0.8103 0.0939 -0.2547 0.048 1.000 . Uiso c ? H(3) 0.4837 0.1534 -0.0846 0.048 1.000 . Uiso c ? H(5) 1.1154 0.1382 0.3225 0.071 1.000 . Uiso c ? H(6) 1.2942 0.1123 0.2408 0.071 1.000 . Uiso c ? H(7) 1.0167 0.1320 -0.0956 0.048 1.000 . Uiso c ? H(8) 0.9776 0.2255 -0.1256 0.069 1.000 . Uiso c ? H(10) 0.6127 0.2173 -0.2287 0.059 1.000 . Uiso c ? H(11) 0.3550 0.1791 -0.4077 0.067 1.000 . Uiso c ? H(12) 0.5699 0.1825 -0.5156 0.067 1.000 . Uiso c ? H(13) 0.5482 0.1005 -0.4656 0.061 1.000 . Uiso c ? H(20) 0.9319 0.0815 0.4735 0.073 1.000 . Uiso c ? H(21) 0.8364 0.0309 0.3203 0.073 1.000 . Uiso c ? H(22) 1.1009 0.0492 0.4072 0.073 1.000 . Uiso c ? H(14) 0.5595 -0.0147 -0.1785 0.084 1.000 . Uiso c ? H(15) 0.5954 0.0100 -0.3468 0.084 1.000 . Uiso c ? H(17) 0.8541 0.2088 0.1865 0.060 1.000 . Uiso c ? H(18) 0.7605 0.2343 0.0585 0.060 1.000 . Uiso c ? H(4) 1.0046 0.0730 0.1251 0.058 1.000 . Uiso c ? H(9) 1.1447 0.1966 -0.2156 0.069 1.000 . Uiso c ? H(16) 0.7580 0.0090 -0.2010 0.084 1.000 . Uiso c ? H(19) 0.6177 0.1986 0.1600 0.060 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) 0.062(3) 0.060(2) 0.066(3) -0.002(2) -0.004(2) 0.003(2) O(2) 0.076(3) 0.061(3) 0.095(3) -0.018(2) 0.027(3) -0.009(2) O(3) 0.051(2) 0.050(2) 0.044(2) -0.011(2) 0.009(2) 0.004(2) O(4) 0.061(3) 0.056(2) 0.096(3) -0.015(2) 0.002(2) -0.003(2) O(5) 0.134(4) 0.058(3) 0.058(3) 0.009(3) 0.024(3) 0.004(2) C(1) 0.063(4) 0.036(3) 0.060(4) -0.003(3) 0.006(3) -0.022(3) C(2) 0.065(4) 0.033(3) 0.036(3) -0.005(3) -0.002(3) -0.003(2) C(3) 0.053(3) 0.030(3) 0.035(3) 0.002(2) -0.004(2) -0.002(2) C(4) 0.060(3) 0.020(2) 0.042(3) 0.000(2) 0.001(3) 0.001(2) C(5) 0.037(3) 0.020(2) 0.046(3) 0.004(2) 0.000(2) 0.002(2) C(6) 0.047(3) 0.029(3) 0.035(3) -0.004(2) -0.000(3) -0.017(2) C(7) 0.053(3) 0.038(3) 0.047(3) -0.001(3) 0.004(3) -0.007(3) C(8) 0.060(4) 0.056(3) 0.056(4) -0.010(3) 0.009(3) -0.006(3) C(9) 0.035(3) 0.037(3) 0.069(4) -0.006(3) 0.014(3) -0.013(3) C(10) 0.047(3) 0.020(2) 0.052(3) -0.002(2) 0.007(3) 0.003(2) C(11) 0.066(4) 0.036(3) 0.067(4) 0.001(3) 0.013(3) -0.001(3) C(12) 0.079(4) 0.025(3) 0.057(4) 0.005(3) 0.014(3) 0.011(3) C(13) 0.071(4) 0.020(3) 0.054(3) 0.007(3) 0.006(3) 0.005(2) C(14) 0.088(4) 0.037(3) 0.043(3) 0.009(3) -0.011(3) 0.010(3) C(15) 0.067(4) 0.050(3) 0.035(3) 0.002(3) 0.003(3) -0.009(3) C(16) 0.102(5) 0.034(3) 0.074(4) 0.003(3) 0.007(4) 0.005(3) C(17) 0.058(3) 0.034(3) 0.053(3) -0.004(3) 0.006(3) -0.008(3) C(18) 0.074(4) 0.058(3) 0.043(3) 0.004(3) -0.010(3) 0.016(3) #============================================================================== # REFINEMENT DATA _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) + 0.00007|Fo|^2^]' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1331 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.2044 _refine_ls_R_factor_gt 0.0930 _refine_ls_wR_factor_all 0.1000 _refine_ls_wR_factor_ref 0.0940 _refine_ls_goodness_of_fit_all 2.292 _refine_ls_goodness_of_fit_ref 3.210 _refine_ls_shift/su_max 0.0000 _refine_ls_shift/su_mean 0.0000 _refine_diff_density_min -0.29 _refine_diff_density_max 0.41 #============================================================================== # MOLECULAR GEOMETRY _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(1) 1.39(1) . . ? O(1) C(15) 1.45(1) . . ? O(2) C(1) 1.20(1) . . ? O(3) C(6) 1.215(9) . . ? O(4) C(9) 1.218(9) . . ? O(5) C(12) 1.24(1) . . ? C(1) C(2) 1.49(1) . . ? C(2) C(3) 1.53(1) . . ? C(2) C(16) 1.54(1) . . ? C(2) H(1) 0.77 . . no C(3) C(4) 1.56(1) . . ? C(3) C(15) 1.53(1) . . ? C(3) H(2) 1.15 . . no C(4) C(5) 1.54(1) . . ? C(4) C(13) 1.58(1) . . ? C(4) H(3) 1.19 . . no C(5) C(6) 1.58(1) . . ? C(5) C(10) 1.51(1) . . ? C(5) C(17) 1.56(1) . . ? C(6) C(7) 1.48(1) . . ? C(7) C(8) 1.51(1) . . ? C(7) C(18) 1.54(1) . . ? C(7) H(4) 0.94 . . no C(8) C(9) 1.52(1) . . ? C(8) H(5) 0.71 . . no C(8) H(6) 1.17 . . no C(9) C(10) 1.50(1) . . ? C(10) C(11) 1.55(1) . . ? C(10) H(7) 0.96 . . no C(11) C(12) 1.48(1) . . ? C(11) H(8) 0.86 . . no C(11) H(9) 0.97 . . no C(12) C(13) 1.49(1) . . ? C(13) C(14) 1.51(1) . . ? C(13) H(10) 0.95 . . no C(14) C(15) 1.57(1) . . ? C(14) H(11) 1.18 . . no C(14) H(12) 1.00 . . no C(15) H(13) 0.78 . . no C(16) H(14) 0.96 . . no C(16) H(15) 0.92 . . no C(16) H(16) 0.97 . . no C(17) H(17) 0.93 . . no C(17) H(18) 0.97 . . no C(17) H(19) 0.97 . . no C(18) H(20) 1.08 . . no C(18) H(21) 1.16 . . no C(18) H(22) 1.10 . . 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(1) O(1) C(15) 108.5(7) . . . ? O(1) C(1) O(2) 118.4(9) . . . ? O(1) C(1) C(2) 109.3(8) . . . ? O(2) C(1) C(2) 132(1) . . . ? C(1) C(2) C(3) 105.1(7) . . . ? C(1) C(2) C(16) 110.8(7) . . . ? C(1) C(2) H(1) 109.1 . . . no C(3) C(2) C(16) 111.5(7) . . . ? C(3) C(2) H(1) 113.7 . . . no C(16) C(2) H(1) 106.5 . . . no C(2) C(3) C(4) 116.2(7) . . . ? C(2) C(3) C(15) 99.8(7) . . . ? C(2) C(3) H(2) 113.0 . . . no C(4) C(3) C(15) 101.9(6) . . . ? C(4) C(3) H(2) 110.7 . . . no C(15) C(3) H(2) 114.4 . . . no C(3) C(4) C(5) 117.7(7) . . . ? C(3) C(4) C(13) 100.0(6) . . . ? C(3) C(4) H(3) 107.0 . . . no C(5) C(4) C(13) 112.4(7) . . . ? C(5) C(4) H(3) 112.5 . . . no C(13) C(4) H(3) 106.0 . . . no C(4) C(5) C(6) 110.1(6) . . . ? C(4) C(5) C(10) 112.5(7) . . . ? C(4) C(5) C(17) 107.3(6) . . . ? C(6) C(5) C(10) 110.3(7) . . . ? C(6) C(5) C(17) 104.2(6) . . . ? C(10) C(5) C(17) 112.1(6) . . . ? O(3) C(6) C(5) 118.8(8) . . . ? O(3) C(6) C(7) 125.1(8) . . . ? C(5) C(6) C(7) 116.1(7) . . . ? C(6) C(7) C(8) 113.2(7) . . . ? C(6) C(7) C(18) 111.8(7) . . . ? C(6) C(7) H(4) 106.3 . . . no C(8) C(7) C(18) 112.2(8) . . . ? C(8) C(7) H(4) 106.2 . . . no C(18) C(7) H(4) 106.4 . . . no C(7) C(8) C(9) 114.6(8) . . . ? C(7) C(8) H(5) 100.9 . . . no C(7) C(8) H(6) 116.8 . . . no C(9) C(8) H(5) 109.6 . . . no C(9) C(8) H(6) 98.6 . . . no H(5) C(8) H(6) 116.8 . . . no O(4) C(9) C(8) 122.4(9) . . . ? O(4) C(9) C(10) 123.5(8) . . . ? C(8) C(9) C(10) 114.1(7) . . . ? C(5) C(10) C(9) 110.8(7) . . . ? C(5) C(10) C(11) 112.8(7) . . . ? C(5) C(10) H(7) 105.0 . . . no C(9) C(10) C(11) 112.7(7) . . . ? C(9) C(10) H(7) 113.3 . . . no C(11) C(10) H(7) 101.7 . . . no C(10) C(11) C(12) 109.0(8) . . . ? C(10) C(11) H(8) 103.3 . . . no C(10) C(11) H(9) 109.0 . . . no C(12) C(11) H(8) 100.3 . . . no C(12) C(11) H(9) 108.6 . . . no H(8) C(11) H(9) 125.6 . . . no O(5) C(12) C(11) 120(1) . . . ? O(5) C(12) C(13) 120(1) . . . ? C(11) C(12) C(13) 120.2(9) . . . ? C(4) C(13) C(12) 109.3(7) . . . ? C(4) C(13) C(14) 103.8(7) . . . ? C(4) C(13) H(10) 105.4 . . . no C(12) C(13) C(14) 116.4(8) . . . ? C(12) C(13) H(10) 111.4 . . . no C(14) C(13) H(10) 109.7 . . . no C(13) C(14) C(15) 104.2(7) . . . ? C(13) C(14) H(11) 117.8 . . . no C(13) C(14) H(12) 104.4 . . . no C(15) C(14) H(11) 101.9 . . . no C(15) C(14) H(12) 118.5 . . . no H(11) C(14) H(12) 110.6 . . . no O(1) C(15) C(3) 107.4(7) . . . ? O(1) C(15) C(14) 108.6(8) . . . ? O(1) C(15) H(13) 109.1 . . . no C(3) C(15) C(14) 107.8(7) . . . ? C(3) C(15) H(13) 113.4 . . . no C(14) C(15) H(13) 110.5 . . . no C(2) C(16) H(14) 108.5 . . . no C(2) C(16) H(15) 111.2 . . . no C(2) C(16) H(16) 108.4 . . . no H(14) C(16) H(15) 110.9 . . . no H(14) C(16) H(16) 107.0 . . . no H(15) C(16) H(16) 110.7 . . . no C(5) C(17) H(17) 100.0 . . . no C(5) C(17) H(18) 115.8 . . . no C(5) C(17) H(19) 108.4 . . . no H(17) C(17) H(18) 91.4 . . . no H(17) C(17) H(19) 121.7 . . . no H(18) C(17) H(19) 117.8 . . . no C(7) C(18) H(20) 108.5 . . . no C(7) C(18) H(21) 106.3 . . . no C(7) C(18) H(22) 104.1 . . . no H(20) C(18) H(21) 120.6 . . . no H(20) C(18) H(22) 94.7 . . . no H(21) C(18) H(22) 121.1 . . . 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(8) 3.47(1) . 1_454 no O(1) C(18) 3.48(1) . 1_454 no O(2) C(10) 3.53(1) . 1_455 no O(2) C(18) 3.57(1) . 3_655 no O(3) C(15) 3.44(1) . 1_556 no O(3) C(8) 3.51(1) . 1_455 no O(4) C(12) 3.10(1) . 4 no O(4) C(13) 3.30(1) . 4 no O(4) O(5) 3.357(9) . 4 no O(4) C(17) 3.36(1) . 1_655 no O(5) C(8) 3.42(1) . 1_554 no O(5) C(17) 3.55(1) . 1_554 no C(11) C(17) 3.59(1) . 4_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(1) C(2) C(3) . . . . 20.5(9) no O(1) C(1) C(2) C(16) . . . . -100.1(8) no O(1) C(15) C(3) C(2) . . . . 29.6(8) no O(1) C(15) C(3) C(4) . . . . -90.0(7) no O(1) C(15) C(14) C(13) . . . . 117.6(8) no O(2) C(1) O(1) C(15) . . . . 178.2(8) no O(2) C(1) C(2) C(3) . . . . -159(1) no O(2) C(1) C(2) C(16) . . . . 81(1) no O(3) C(6) C(5) C(4) . . . . -50.1(9) no O(3) C(6) C(5) C(10) . . . . -174.8(7) no O(3) C(6) C(5) C(17) . . . . 64.7(9) no O(3) C(6) C(7) C(8) . . . . -136.8(8) no O(3) C(6) C(7) C(18) . . . . -9(1) no O(4) C(9) C(8) C(7) . . . . 172.8(8) no O(4) C(9) C(10) C(5) . . . . -123.0(9) no O(4) C(9) C(10) C(11) . . . . 4(1) no O(5) C(12) C(11) C(10) . . . . -125.9(8) no O(5) C(12) C(13) C(4) . . . . 128.1(8) no O(5) C(12) C(13) C(14) . . . . 11(1) no C(1) O(1) C(15) C(3) . . . . -18.7(8) no C(1) O(1) C(15) C(14) . . . . -135.1(7) no C(1) C(2) C(3) C(4) . . . . 79.1(8) no C(1) C(2) C(3) C(15) . . . . -29.5(8) no C(2) C(1) O(1) C(15) . . . . -1.3(9) no C(2) C(3) C(4) C(5) . . . . 87.2(9) no C(2) C(3) C(4) C(13) . . . . -150.8(7) no C(2) C(3) C(15) C(14) . . . . 146.4(7) no C(3) C(4) C(5) C(6) . . . . -60.0(9) no C(3) C(4) C(5) C(10) . . . . 63.4(9) no C(3) C(4) C(5) C(17) . . . . -172.8(7) no C(3) C(4) C(13) C(12) . . . . -79.1(9) no C(3) C(4) C(13) C(14) . . . . 45.7(8) no C(3) C(15) C(14) C(13) . . . . 2(1) no C(4) C(3) C(2) C(16) . . . . -160.7(7) no C(4) C(3) C(15) C(14) . . . . 26.8(9) no C(4) C(5) C(6) C(7) . . . . 131.0(7) no C(4) C(5) C(10) C(9) . . . . -177.9(6) no C(4) C(5) C(10) C(11) . . . . 54.7(9) no C(4) C(13) C(12) C(11) . . . . -49(1) no C(4) C(13) C(14) C(15) . . . . -29.2(9) no C(5) C(4) C(3) C(15) . . . . -165.5(7) no C(5) C(4) C(13) C(12) . . . . 46.6(9) no C(5) C(4) C(13) C(14) . . . . 171.5(7) no C(5) C(6) C(7) C(8) . . . . 42(1) no C(5) C(6) C(7) C(18) . . . . 170.1(7) no C(5) C(10) C(9) C(8) . . . . 55.4(9) no C(5) C(10) C(11) C(12) . . . . -51.7(9) no C(6) C(5) C(4) C(13) . . . . -175.5(6) no C(6) C(5) C(10) C(9) . . . . -54.6(8) no C(6) C(5) C(10) C(11) . . . . 178.0(7) no C(6) C(7) C(8) C(9) . . . . -43(1) no C(7) C(6) C(5) C(10) . . . . 6.3(9) no C(7) C(6) C(5) C(17) . . . . -114.2(7) no C(7) C(8) C(9) C(10) . . . . -6(1) no C(8) C(9) C(10) C(11) . . . . -177.1(7) no C(9) C(8) C(7) C(18) . . . . -170.4(7) no C(9) C(10) C(5) C(17) . . . . 61.1(9) no C(9) C(10) C(11) C(12) . . . . -178.0(7) no C(10) C(5) C(4) C(13) . . . . -52.0(9) no C(10) C(11) C(12) C(13) . . . . 52(1) no C(11) C(10) C(5) C(17) . . . . -66.4(9) no C(11) C(12) C(13) C(14) . . . . -166.6(7) no C(12) C(13) C(14) C(15) . . . . 91.0(8) no C(13) C(4) C(3) C(15) . . . . -43.5(8) no C(13) C(4) C(5) C(17) . . . . 71.8(8) no C(15) C(3) C(2) C(16) . . . . 90.7(8) no #------------------------------------------------------------------------------ #============================================================================== # End of CIF #============================================================================== #==END