# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2002 data_MGB49 _database_code_CSD 188927 _journal_coden_Cambridge 440 #------------------------------------------------------------------------------ _audit_creation_date '2002-07-01' _audit_creation_method 'by teXsan v1.8' _audit_update_record ; 1999-02-24 dcrh does report 2002-07-01 acwillis does cif 2002-07-02 passes checkcif with warnings: * Mass attenuation coefficients for absorption from International Tables for X-ray Crystallography Vol IV (1974) Table 2.1C. * crystal small, data weak, so refln/parameter ratio low. Non-centrosymmetric space group. * Data can only be collected to 2theta 120 deg on a AFC6R diffractometer when the evacuated beam tunnel in used. ; #------------------------------------------------------------------------------ _vrf_ABSMU_01_MGB49 ; PROBLEM: Alert B The ratio of given/expected absorption coefficient lies * Mass attenuation coefficients for absorption from International Tables for X-ray Crystallography Vol IV (1974) Table 2.1C. ; _vrf_REFNR_01_MGB49 ; PROBLEM: Alert A Ratio of reflections to parameters is < 4 for a * crystal small, data weak, so refln/parameter ratio low [3.98]. Non-centrosymmetric space group. Distances and angles appear sensible and adp's reasonable. ; _vrf_THETM_01_MGB49 ; PROBLEM: Alert B The value of sine(theta_max)/wavelength is less than 0.575 * Data can only be collected to 2theta 120 deg on a AFC6R diffractometer when the evacuated beam tunnel in used. ; #------------------------------------------------------------------------------ _publ_requested_journal ' New Journal of Chemistry' _publ_requested_category ' fo' _publ_contact_author_name ' Martin G. Banwell ' _publ_contact_author_address ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_coeditor_name ? _publ_contact_author_phone ' 61 2 6125 4109 ' _publ_contact_author_fax ' 61 2 6125 0750 ' _publ_contact_author_email ' willis@rsc.anu.edu.au ' loop_ _publ_author_name _publ_author_address ' Martin G. Banwell ' ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; ' David C. R. Hockless ' ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; ' Malcolm D. McLeod ' ; School of Chemistry, F11, The University of Sydney, NSW 2006, Australia ; _publ_section_title ; Chemoenzymatic total syntheses of the sesquiterpene (-)-patchoulenone ; _publ_section_title_footnote ' ENTER ANY FOOTNOTES TO TITLE ' _publ_section_abstract ; ENTER ABSTRACT ; _publ_section_exptl_refinement ; ENTER EXPERIMENTAL SECTION ; _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. Zachariasen, W. H. (1967). Acta Cryst. 23, 558-564. Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. ; _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. 1994) ; _computing_structure_refinement 'teXsan (MSC, 1992-1997)' _computing_publication_material 'teXsan (MSC, 1992-1997)' #------------------------------------------------------------------------------ _cell_length_a 10.017(1) _cell_length_b 9.245(2) _cell_length_c 11.062(1) _cell_angle_alpha 90 _cell_angle_beta 112.073(7) _cell_angle_gamma 90 _cell_volume 949.3(2) _cell_formula_units_Z 2 _cell_measurement_temperature 296.2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 16.2 _cell_measurement_theta_max 25.3 #------------------------------------------------------------------------------ _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' #------------------------------------------------------------------------------ _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _exptl_crystal_description 'plate' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.06 _exptl_crystal_density_diffrn 1.142 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 326.48 _chemical_formula_analytical ? _chemical_formula_sum 'C22 H30 O2 ' _chemical_formula_moiety 'C22 H30 O2 ' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 356.00 _exptl_absorpt_coefficient_mu 0.518 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ; \y scans (North,Phillips & Matthews, 1968) ; _exptl_absorpt_correction_T_max .969 _exptl_absorpt_correction_T_min .907 _exptl_special_details ; The scan width was (1.20+0.30tan\q)\% with an \w scan speed of 16\% 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. Data can only be collected to 2theta 120 deg on a AFC6R diffractometer when the evacuated beam tunnel in used. Mass attenuation coefficients for absorption from International Tables for X-ray Crystallography, Vol IV (1974) Table 2.1C. ; #------------------------------------------------------------------------------ _diffrn_special_details ; ? ; _diffrn_ambient_temperature 296.2 _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device_type 'Rigaku AFC6R' _diffrn_measurement_device_details ; Rigaku AFC6R diffractometer with extended arm and evacuated collimator and beam tunnel. Data cannot be collected beyond \y 60 deg in this configuration. ; _diffrn_measurement_method \w-2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% -0.39 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 2 0 0 0 2 0 0 1 1 _diffrn_reflns_number 1621 _reflns_number_total 1520 _reflns_number_gt 864 _reflns_threshold_expression I>3.00\s(I) _diffrn_reflns_av_R_equivalents 0.03340 _diffrn_reflns_av_sigmaI/netI 0.100 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 4.32 _diffrn_reflns_theta_max 60.02 _diffrn_measured_fraction_theta_max 1. _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 -0.10369 _diffrn_orient_matrix_UB_12 -0.00979 _diffrn_orient_matrix_UB_13 -0.01218 _diffrn_orient_matrix_UB_21 0.02441 _diffrn_orient_matrix_UB_22 0.02693 _diffrn_orient_matrix_UB_23 0.09343 _diffrn_orient_matrix_UB_31 -0.01603 _diffrn_orient_matrix_UB_32 0.10431 _diffrn_orient_matrix_UB_33 -0.02526 #------------------------------------------------------------------------------ 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 44 0.017 0.009 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H 0 60 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; O 0 4 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) 1.1378(4) 0.0219 0.8677(4) 0.062(2) 1.000 . Uani d ? O(2) 1.0983(5) 0.2078(8) 1.0418(4) 0.061(2) 1.000 . Uani d ? C(1) 1.3396(7) -0.054(1) 1.0509(7) 0.057(2) 1.000 . Uani d ? C(2) 1.1726(6) -0.028(1) 0.9966(6) 0.053(2) 1.000 . Uani d ? C(3) 1.1177(6) 0.082(1) 1.0725(6) 0.052(2) 1.000 . Uani d ? C(4) 1.0672(7) 0.019(1) 1.1782(6) 0.062(2) 1.000 . Uani d ? C(5) 1.1546(7) 0.076(1) 1.3139(6) 0.076(3) 1.000 . Uani d ? C(6) 1.3118(7) 0.023(1) 1.3702(6) 0.071(3) 1.000 . Uani d ? C(7) 1.3805(7) 0.041(1) 1.2696(6) 0.054(2) 1.000 . Uani d ? C(8) 1.4119(7) 0.172(1) 1.2376(7) 0.057(3) 1.000 . Uani d ? C(9) 1.4505(7) 0.199(1) 1.1212(7) 0.077(3) 1.000 . Uani d ? C(10) 1.4199(7) 0.073(1) 1.0223(7) 0.073(3) 1.000 . Uani d ? C(11) 1.4030(7) -0.090(1) 1.1978(7) 0.052(3) 1.000 . Uani d ? C(12) 0.9056(7) 0.057(1) 1.1375(7) 0.090(3) 1.000 . Uani d ? C(13) 1.4001(9) 0.311(1) 1.3016(8) 0.091(3) 1.000 . Uani d ? C(14) 1.3393(8) -0.234(1) 1.2214(7) 0.074(3) 1.000 . Uani d ? C(15) 1.5660(7) -0.120(1) 1.2399(7) 0.082(3) 1.000 . Uani d ? C(16) 0.9867(7) 0.018(1) 0.7900(6) 0.066(3) 1.000 . Uani d ? C(17) 0.9578(7) 0.108(1) 0.6699(6) 0.053(2) 1.000 . Uani d ? C(18) 0.8221(7) 0.100(1) 0.5701(7) 0.067(3) 1.000 . Uani d ? C(19) 0.7913(7) 0.184(1) 0.4607(6) 0.074(3) 1.000 . Uani d ? C(20) 0.8889(9) 0.282(1) 0.4492(7) 0.079(3) 1.000 . Uani d ? C(21) 1.0233(9) 0.290(1) 0.5506(8) 0.090(3) 1.000 . Uani d ? C(22) 1.0559(7) 0.204(1) 0.6585(7) 0.075(3) 1.000 . Uani d ? H(1) 1.3563 -0.1350 1.0061 0.068 1.000 . Uiso c ? H(2) 1.1259 -0.1181 0.9937 0.063 1.000 . Uiso c ? H(4) 1.0767 -0.0837 1.1789 0.074 1.000 . Uiso c ? H(5a) 1.1089 0.0466 1.3711 0.091 1.000 . Uiso c ? H(5b) 1.1551 0.1789 1.3098 0.091 1.000 . Uiso c ? H(6a) 1.3137 -0.0759 1.3932 0.085 1.000 . Uiso c ? H(6b) 1.3644 0.0783 1.4456 0.085 1.000 . Uiso c ? H(9a) 1.3974 0.2807 1.0763 0.092 1.000 . Uiso c ? H(9b) 1.5506 0.2196 1.1518 0.092 1.000 . Uiso c ? H(10a) 1.3639 0.1096 0.9381 0.087 1.000 . Uiso c ? H(10b) 1.5094 0.0386 1.0227 0.087 1.000 . Uiso c ? H(12a) 0.8527 0.0168 1.0541 0.107 1.000 . Uiso c ? H(12b) 0.8707 0.0185 1.1997 0.107 1.000 . Uiso c ? H(12c) 0.8945 0.1591 1.1339 0.107 1.000 . Uiso c ? H(13a) 1.3116 0.3572 1.2519 0.109 1.000 . Uiso c ? H(13b) 1.4034 0.2924 1.3870 0.109 1.000 . Uiso c ? H(13c) 1.4780 0.3728 1.3064 0.109 1.000 . Uiso c ? H(14a) 1.3520 -0.3066 1.1656 0.089 1.000 . Uiso c ? H(14b) 1.2395 -0.2222 1.2034 0.089 1.000 . Uiso c ? H(14c) 1.3873 -0.2628 1.3097 0.089 1.000 . Uiso c ? H(15a) 1.5798 -0.2120 1.2078 0.099 1.000 . Uiso c ? H(15b) 1.6084 -0.0473 1.2053 0.099 1.000 . Uiso c ? H(15c) 1.6100 -0.1197 1.3324 0.099 1.000 . Uiso c ? H(16a) 0.9578 -0.0791 0.7656 0.080 1.000 . Uiso c ? H(16b) 0.9342 0.0556 0.8388 0.080 1.000 . Uiso c ? H(18) 0.7510 0.0370 0.5778 0.080 1.000 . Uiso c ? H(19) 0.7003 0.1746 0.3913 0.088 1.000 . Uiso c ? H(20) 0.8656 0.3428 0.3746 0.094 1.000 . Uiso c ? H(21) 1.0933 0.3560 0.5446 0.108 1.000 . Uiso c ? H(22) 1.1481 0.2119 0.7266 0.089 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) 0.048(3) 0.088(4) 0.049(3) 0.000(3) 0.018(2) 0.006(3) O(2) 0.065(3) 0.045(4) 0.071(3) 0.005(3) 0.024(3) 0.010(3) C(1) 0.051(4) 0.057(6) 0.066(5) 0.000(4) 0.028(4) -0.011(4) C(2) 0.043(4) 0.058(5) 0.054(4) 0.005(4) 0.015(3) 0.001(4) C(3) 0.038(4) 0.060(6) 0.059(4) -0.003(4) 0.017(3) 0.001(5) C(4) 0.061(4) 0.066(6) 0.066(4) 0.006(5) 0.031(4) 0.014(5) C(5) 0.074(5) 0.101(8) 0.063(4) 0.011(5) 0.038(4) 0.006(5) C(6) 0.071(5) 0.081(6) 0.059(4) 0.018(6) 0.024(4) 0.008(5) C(7) 0.050(4) 0.063(6) 0.047(4) 0.006(4) 0.015(3) 0.006(4) C(8) 0.044(4) 0.056(7) 0.063(5) -0.002(4) 0.012(4) -0.003(5) C(9) 0.059(5) 0.083(7) 0.085(5) -0.003(5) 0.022(4) 0.021(6) C(10) 0.058(4) 0.097(8) 0.066(5) -0.006(5) 0.027(4) 0.006(5) C(11) 0.044(4) 0.055(6) 0.052(5) 0.005(4) 0.010(4) 0.006(4) C(12) 0.058(4) 0.127(9) 0.100(6) 0.010(6) 0.049(4) 0.010(7) C(13) 0.084(6) 0.063(7) 0.112(7) -0.001(5) 0.021(5) -0.016(6) C(14) 0.074(5) 0.058(6) 0.076(5) 0.014(5) 0.011(4) 0.001(5) C(15) 0.061(4) 0.091(8) 0.088(6) 0.016(5) 0.020(4) -0.005(6) C(16) 0.054(4) 0.072(7) 0.071(5) -0.013(5) 0.020(4) -0.001(5) C(17) 0.050(4) 0.061(6) 0.048(4) -0.008(4) 0.020(3) -0.009(4) C(18) 0.055(4) 0.076(7) 0.072(5) -0.018(5) 0.027(4) -0.015(5) C(19) 0.074(5) 0.093(8) 0.044(4) 0.011(6) 0.011(4) -0.003(5) C(20) 0.093(6) 0.091(8) 0.050(5) 0.008(7) 0.025(5) 0.010(6) C(21) 0.084(6) 0.093(8) 0.093(6) -0.017(6) 0.033(6) 0.012(7) C(22) 0.052(4) 0.091(8) 0.065(5) -0.014(5) 0.003(4) 0.013(6) #------------------------------------------------------------------------------ _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 'Zachariasen (1967)' _refine_ls_extinction_coef 0.0000034(6) _refine_ls_extinction_expression 'equ(3) Acta Cryst.(1968) A24, p213.' _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _chemical_absolute_configuration syn _refine_ls_number_reflns 864 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.1080 _refine_ls_R_factor_gt 0.0417 _refine_ls_wR_factor_all 0.0394 _refine_ls_wR_factor_ref 0.0329 _refine_ls_goodness_of_fit_all 1.511 _refine_ls_goodness_of_fit_ref 1.790 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.0001 _refine_diff_density_min -0.11 _refine_diff_density_max 0.13 #------------------------------------------------------------------------------ _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(2) 1.411(7) . . yes O(1) C(16) 1.433(7) . . yes O(2) C(3) 1.209(8) . . yes C(1) C(2) 1.568(8) . . yes C(1) C(10) 1.52(1) . . yes C(1) C(11) 1.544(9) . . yes C(1) H(1) 0.95 . . no C(2) C(3) 1.545(9) . . yes C(2) H(2) 0.95 . . no C(3) C(4) 1.551(9) . . yes C(4) C(5) 1.523(9) . . yes C(4) C(12) 1.549(8) . . yes C(4) H(4) 0.95 . . no C(5) C(6) 1.540(8) . . yes C(5) H(5a) 0.95 . . no C(5) H(5b) 0.95 . . no C(6) C(7) 1.521(9) . . yes C(6) H(6a) 0.95 . . no C(6) H(6b) 0.95 . . no C(7) C(8) 1.33(1) . . yes C(7) C(11) 1.51(1) . . yes C(8) C(9) 1.497(9) . . yes C(8) C(13) 1.49(1) . . yes C(9) C(10) 1.55(1) . . yes C(9) H(9a) 0.95 . . no C(9) H(9b) 0.95 . . no C(10) H(10a) 0.95 . . no C(10) H(10b) 0.95 . . no C(11) C(14) 1.54(1) . . yes C(11) C(15) 1.546(9) . . yes C(12) H(12a) 0.95 . . no C(12) H(12b) 0.95 . . no C(12) H(12c) 0.95 . . no C(13) H(13a) 0.95 . . no C(13) H(13b) 0.95 . . no C(13) H(13c) 0.95 . . no C(14) H(14a) 0.95 . . no C(14) H(14b) 0.95 . . no C(14) H(14c) 0.95 . . no C(15) H(15a) 0.95 . . no C(15) H(15b) 0.95 . . no C(15) H(15c) 0.95 . . no C(16) C(17) 1.502(9) . . yes C(16) H(16a) 0.95 . . no C(16) H(16b) 0.95 . . no C(17) C(18) 1.394(8) . . yes C(17) C(22) 1.367(9) . . yes C(18) C(19) 1.372(9) . . yes C(18) H(18) 0.95 . . no C(19) C(20) 1.37(1) . . yes C(19) H(19) 0.95 . . no C(20) C(21) 1.393(9) . . yes C(20) H(20) 0.95 . . no C(21) C(22) 1.37(1) . . yes C(21) H(21) 0.95 . . no C(22) H(22) 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(2) O(1) C(16) 113.7(5) . . . yes C(2) C(1) C(10) 112.1(6) . . . yes C(2) C(1) C(11) 113.2(5) . . . yes C(2) C(1) H(1) 106.9 . . . no C(10) C(1) C(11) 110.3(6) . . . yes C(10) C(1) H(1) 106.9 . . . no C(11) C(1) H(1) 106.9 . . . no O(1) C(2) C(1) 105.0(5) . . . yes O(1) C(2) C(3) 109.3(6) . . . yes O(1) C(2) H(2) 108.8 . . . no C(1) C(2) C(3) 115.9(5) . . . yes C(1) C(2) H(2) 108.8 . . . no C(3) C(2) H(2) 108.8 . . . no O(2) C(3) C(2) 122.2(7) . . . yes O(2) C(3) C(4) 120.8(7) . . . yes C(2) C(3) C(4) 116.5(6) . . . yes C(3) C(4) C(5) 112.5(6) . . . yes C(3) C(4) C(12) 107.2(5) . . . yes C(3) C(4) H(4) 108.7 . . . no C(5) C(4) C(12) 110.9(6) . . . yes C(5) C(4) H(4) 108.7 . . . no C(12) C(4) H(4) 108.7 . . . no C(4) C(5) C(6) 114.1(6) . . . yes C(4) C(5) H(5a) 108.3 . . . no C(4) C(5) H(5b) 108.3 . . . no C(6) C(5) H(5a) 108.2 . . . no C(6) C(5) H(5b) 108.3 . . . no H(5a) C(5) H(5b) 109.5 . . . no C(5) C(6) C(7) 110.2(5) . . . yes C(5) C(6) H(6a) 109.4 . . . no C(5) C(6) H(6b) 109.4 . . . no C(7) C(6) H(6a) 109.3 . . . no C(7) C(6) H(6b) 109.2 . . . no H(6a) C(6) H(6b) 109.4 . . . no C(6) C(7) C(8) 120.6(8) . . . yes C(6) C(7) C(11) 119.8(8) . . . yes C(8) C(7) C(11) 119.5(6) . . . yes C(7) C(8) C(9) 122.7(7) . . . yes C(7) C(8) C(13) 126.1(7) . . . yes C(9) C(8) C(13) 110.9(8) . . . yes C(8) C(9) C(10) 116.0(7) . . . yes C(8) C(9) H(9a) 107.7 . . . no C(8) C(9) H(9b) 107.7 . . . no C(10) C(9) H(9a) 107.9 . . . no C(10) C(9) H(9b) 107.9 . . . no H(9a) C(9) H(9b) 109.5 . . . no C(1) C(10) C(9) 114.3(6) . . . yes C(1) C(10) H(10a) 108.3 . . . no C(1) C(10) H(10b) 108.3 . . . no C(9) C(10) H(10a) 108.2 . . . no C(9) C(10) H(10b) 108.2 . . . no H(10a) C(10) H(10b) 109.5 . . . no C(1) C(11) C(7) 107.1(6) . . . yes C(1) C(11) C(14) 109.6(6) . . . yes C(1) C(11) C(15) 109.1(6) . . . yes C(7) C(11) C(14) 116.8(6) . . . yes C(7) C(11) C(15) 109.6(6) . . . yes C(14) C(11) C(15) 104.6(7) . . . yes C(4) C(12) H(12a) 109.5 . . . no C(4) C(12) H(12b) 109.5 . . . no C(4) C(12) H(12c) 109.4 . . . no H(12a) C(12) H(12b) 109.5 . . . no H(12a) C(12) H(12c) 109.4 . . . no H(12b) C(12) H(12c) 109.5 . . . no C(8) C(13) H(13a) 109.6 . . . no C(8) C(13) H(13b) 109.5 . . . no C(8) C(13) H(13c) 109.5 . . . no H(13a) C(13) H(13b) 109.4 . . . no H(13a) C(13) H(13c) 109.4 . . . no H(13b) C(13) H(13c) 109.4 . . . no C(11) C(14) H(14a) 109.4 . . . no C(11) C(14) H(14b) 109.5 . . . no C(11) C(14) H(14c) 109.5 . . . no H(14a) C(14) H(14b) 109.5 . . . no H(14a) C(14) H(14c) 109.4 . . . no H(14b) C(14) H(14c) 109.5 . . . no C(11) C(15) H(15a) 109.4 . . . no C(11) C(15) H(15b) 109.5 . . . no C(11) C(15) H(15c) 109.5 . . . no H(15a) C(15) H(15b) 109.5 . . . no H(15a) C(15) H(15c) 109.4 . . . no H(15b) C(15) H(15c) 109.5 . . . no O(1) C(16) C(17) 109.0(6) . . . yes O(1) C(16) H(16a) 109.6 . . . no O(1) C(16) H(16b) 109.6 . . . no C(17) C(16) H(16a) 109.6 . . . no C(17) C(16) H(16b) 109.6 . . . no H(16a) C(16) H(16b) 109.5 . . . no C(16) C(17) C(18) 118.6(6) . . . yes C(16) C(17) C(22) 122.4(6) . . . yes C(18) C(17) C(22) 118.8(7) . . . yes C(17) C(18) C(19) 119.9(7) . . . yes C(17) C(18) H(18) 120.0 . . . no C(19) C(18) H(18) 120.1 . . . no C(18) C(19) C(20) 121.5(7) . . . yes C(18) C(19) H(19) 119.2 . . . no C(20) C(19) H(19) 119.2 . . . no C(19) C(20) C(21) 117.8(8) . . . yes C(19) C(20) H(20) 121.1 . . . no C(21) C(20) H(20) 121.1 . . . no C(20) C(21) C(22) 121.0(9) . . . yes C(20) C(21) H(21) 119.5 . . . no C(22) C(21) H(21) 119.5 . . . no C(17) C(22) C(21) 120.9(7) . . . yes C(17) C(22) H(22) 119.5 . . . no C(21) C(22) H(22) 119.5 . . . 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(2) C(2) 3.556(8) . 2_757 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(2) C(1) C(10) . . . . 46.9(8) no O(1) C(2) C(1) C(11) . . . . 172.6(6) no O(1) C(2) C(3) O(2) . . . . -24.2(9) no O(1) C(2) C(3) C(4) . . . . 147.1(5) no O(1) C(16) C(17) C(18) . . . . 169.5(7) no O(1) C(16) C(17) C(22) . . . . -15(1) no O(2) C(3) C(2) C(1) . . . . 94.2(8) no O(2) C(3) C(4) C(5) . . . . -69.1(8) no O(2) C(3) C(4) C(12) . . . . 53.1(9) no C(1) C(2) O(1) C(16) . . . . 165.4(6) no C(1) C(2) C(3) C(4) . . . . -94.4(7) no C(1) C(10) C(9) C(8) . . . . 6(1) no C(1) C(11) C(7) C(6) . . . . 129.5(6) no C(1) C(11) C(7) C(8) . . . . -45.9(8) no C(2) O(1) C(16) C(17) . . . . 165.1(6) no C(2) C(1) C(10) C(9) . . . . 83.4(8) no C(2) C(1) C(11) C(7) . . . . -64.1(7) no C(2) C(1) C(11) C(14) . . . . 63.4(8) no C(2) C(1) C(11) C(15) . . . . 177.4(7) no C(2) C(3) C(4) C(5) . . . . 119.4(7) no C(2) C(3) C(4) C(12) . . . . -118.5(7) no C(3) C(2) O(1) C(16) . . . . -69.6(7) no C(3) C(2) C(1) C(10) . . . . -73.8(8) no C(3) C(2) C(1) C(11) . . . . 51.8(8) no C(3) C(4) C(5) C(6) . . . . -68.8(9) no C(4) C(5) C(6) C(7) . . . . 48(1) no C(5) C(6) C(7) C(8) . . . . 70.9(9) no C(5) C(6) C(7) C(11) . . . . -104.5(8) no C(6) C(5) C(4) C(12) . . . . 171.2(7) no C(6) C(7) C(8) C(9) . . . . -167.0(6) no C(6) C(7) C(8) C(13) . . . . 7(1) no C(6) C(7) C(11) C(14) . . . . 6.2(9) no C(6) C(7) C(11) C(15) . . . . -112.4(7) no C(7) C(8) C(9) C(10) . . . . 13(1) no C(7) C(11) C(1) C(10) . . . . 62.4(7) no C(8) C(7) C(11) C(14) . . . . -169.1(7) no C(8) C(7) C(11) C(15) . . . . 72.2(9) no C(9) C(8) C(7) C(11) . . . . 8(1) no C(9) C(10) C(1) C(11) . . . . -43.8(8) no C(10) C(1) C(11) C(14) . . . . -170.0(6) no C(10) C(1) C(11) C(15) . . . . -56.0(8) no C(10) C(9) C(8) C(13) . . . . -161.5(7) no C(11) C(7) C(8) C(13) . . . . -178.0(7) no C(16) C(17) C(18) C(19) . . . . 178.2(7) no C(16) C(17) C(22) C(21) . . . . -176.6(8) no C(17) C(18) C(19) C(20) . . . . -3(1) no C(17) C(22) C(21) C(20) . . . . 0(2) no C(18) C(17) C(22) C(21) . . . . -1(1) no C(18) C(19) C(20) C(21) . . . . 2(1) no C(19) C(18) C(17) C(22) . . . . 3(1) no C(19) C(20) C(21) C(22) . . . . -1(2) no #------------------------------------------------------------------------------ #===END