# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2001 ---------- X-Sun-Charset: us-ascii X-Sun-Content-Lines: 809 data_ #--------------------------------------------- _publ_contact_author_name 'Takehiko Yamato' _publ_contact_author_email yamatot@cc.saga-u.ac.jp _publ_contact_author_fax '+ 81(0)952/28-8591' _publ_contact_author_phone '+ 81(0)952/28-8679' _publ_contact_author_address ; Department of Applied Chemistry, Faculty of Science and Engineering, Saga University, Honjo-machi 1, Saga-shi Saga 840-8502, Japan ; Cif-file #======================================================================= data_1,2-dimethyl-6,14-dimethoxy[2.4]metacyclophan-1-ene _database_code_CSD 155635 #======================================================================= _audit_creation_date 05-10-00 _audit_creation_method from_MolEN_master_file_using_cif_in _audit_update_record ; ? ; # 1. SUBMISSION DETAILS _publ_contact_author ; Takehiko Yamato Department of Applied Chemistry, Faculty of Science and Engineering, Saga University, Honjo-machi 1, Saga-shi, Saga 840-8502, Japan ; _publ_contact_author_email yamatot@cc.saga-u.ac.jp _publ_contact_author_fax '+ 81(0)952/28-8591' _publ_contact_author_phone '+ 81(0)952/28-8679' _publ_requested_journal 'Journal of Chemical Society, Perkin Trans. 1' _publ_requested_coeditor_name ? # 2. 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_Cambridge 207 _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? # 3. TITLE AND AUTHOR LIST _publ_section_title ; Medium-sized cyclophanes. Part 58. Synthesis and conformational studies of [2.n]metacyclophan-1-enes and [n.1]metacyclophanes ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address 'Takehiko Yamato' ;Department of Applied Chemistry, Faculty of Science and Engineering, Saga University, Honjo-machi 1, Saga-shi, Saga 840-8502, Japan ; 'Koji Fujita' ;Department of Applied Chemistry, Faculty of Science and Engineering, Saga University, Honjo-machi 1, Saga-shi, Saga 840-8502, Japan ; 'Hirohisa Tsuzuki' ;Tohwa Institute for Science, Tohwa University, 1-1-1 Chikushigaoka, Minami-ku, Fukuoka-shi, Fukuoka 815-8510, Japan ; # 4. TEXT _publ_section_abstract ; ? ; _publ_section_comment ; ? ; _publ_section_experimental ; Backgrounds were obtained from analysis of the scan profile (Blessing, Coppens_& Becker, 1974) ; _publ_section_references ; Blessing, R.H., Coppens, P. & Becker, P. (1974). J. Appl. Cryst., 7, 488-492. Burla, M.C., Camalli, M., Cascarano, G.,Giacovazzo, C., Polidori, G., Spagna, R. &Viterbo, D. (1989). SIR. J. Appl. Cryst. 22, 389-393. Enraf-Nonius, CAD4 Operations Manual, Delft, 1977. Fair, C.K. (1990). MolEN, An Interactive Intelligent System for Crystal Structure Analysis, User Manual, Enraf - Nonius, Delft, The Netherlands. International Tables for X-Ray Crystallography, Vol. IV, The Kynoch Press, Birmingham, England, 1974 Johnson, C.K. (1976). ORTEP. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA. Zachariasen, W.H. (1963). Acta Crystallogr., 16, 1139-1144. ; _publ_section_figure_captions ; ? ; _publ_section_acknowledgements ; ? ; #data_1,2-dimethyl-6,14-dimethoxy[2.4]metacyclophan-1-ene # 5. CRYSTAL DATA _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.10 _exptl_crystal_density_method ? _chemical_formula_sum 'C22 H26 O2' _chemical_formula_structural ? _chemical_formula_weight 298.43 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_h-m 'Pbcn' #(No. 60) _cell_length_a 8.6418 (6) _cell_length_b 10.318 (1) _cell_length_c 19.776 (1) _cell_angle_alpha ? _cell_angle_beta ? _cell_angle_gamma ? _cell_volume 1763.4 (2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 30 _cell_measurement_theta_max 32 _cell_formula_units_z 2 _exptl_crystal_density_diffrn 1.124 _exptl_crystal_density_meas ? _diffrn_radiation_type 'Cu KYa' _diffrn_radiation_wavelength 1.54184Y%A _exptl_absorpt_coefficient_mu 5.19 _cell_measurement_temperature 295 _exptl_crystal_F_000 648 # 6. DATA COLLECTION _diffrn_ambient_temperature 295 _diffrn_measurement_device Enraf_Nonius_CAD4 _diffrn_measurement_method Yw/2Yq _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.0000 _exptl_absorpt_correction_T_max 0.0000 _diffrn_reflns_number 2101 _reflns_number_total 1813 _reflns_number_observed 1039 _reflns_observed_criterion >3.0(Ys) _diffrn_reflns_av_R_equivalents 0.025 _diffrn_reflns_theta_min 30.01 _diffrn_reflns_theta_max 31.74 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_max 24 _diffrn_standards_number 5 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% ? # 7. REFINEMENT DATA _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_R_factor_all 0.059 _refine_ls_wR_factor_all ? _refine_ls_wR_factor_obs 0.077 _refine_ls_hydrogen_treatment riding _refine_ls_number_reflns 2101 _refine_ls_number_parameters 110 _refine_ls_number_restraints 132 _refine_ls_goodness_of_fit_all ? _refine_ls_goodness_of_fit_obs 2.51 _refine_ls_weighting_scheme 'calc w=4Fo^2^/ (Ys^2^(Fo^2^) + 0.0016 Fo^4^)' _refine_ls_shift/esd_max 0.02 _refine_diff_density_max 0.269 _refine_diff_density_min -0.328 _refine_ls_extinction_method isotropic_(Zachariasen,_1963) _refine_ls_extinction_coef 1.75E-05 _atom_type_scat_source International_Tables_for_Xray_Crystallography # 8. COMPUTING DATA _computing_data_collection CAD4_(Enraf-Nonius,_1977) _computing_cell_refinement CAD4_(Enraf-Nonius,_1977) _computing_data_reduction PROCESS_MolEN_(Fair,_1990) _computing_structure_solution Direct_methods_(SIR,_Burla_et_al.,_1989) _computing_structure_refinement LSFM_MolEN_(Fair,_1990) _computing_molecular_graphics ORTEP_(Johnson,_1976) _computing_publication_material CIF_IN_MolEN_(Fair,_1990) _refine_ls_abs_structure_details ; ? ; # 9. 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_thermal_displace_type #_atom_site_calc_flag O1 0.9205(3) 0.1414(2) 0.0458(1) 5.38(5) C1 1.0835(4) 0.0822(3) 0.2378(2) 3.98(6) C2 1.1008(4) 0.1095(3) 0.1622(2) 4.33(7) C3 1.0340(3) 0.2385(3) 0.1417(2) 3.66(6) C4 0.9319(4) 0.2498(3) 0.0865(2) 4.23(6) C5 0.8512(4) 0.3631(3) 0.0756(2) 5.03(7) C6 0.8713(4) 0.4674(3) 0.1182(2) 4.76(7) C7 0.9757(3) 0.4649(3) 0.1713(2) 3.71(6) C8 1.0588(3) 0.3495(3) 0.1803(2) 3.64(6) C9 0.9905(4) 0.5813(3) 0.2165(2) 4.11(6) C10 0.9784(4) 0.7092(3) 0.1797(2) 5.50(8) C11 0.8243(6) 0.1490(4) -0.0121(2) 6.8(1) H1 1.126 0.000 0.248 5.0* H2 1.137 0.147 0.262 5.0* H3 1.207 0.107 0.151 5.0* H4 1.047 0.043 0.138 5.0* H5 0.782 0.370 0.038 5.0* H6 0.811 0.543 0.112 5.0* H7 1.136 0.347 0.214 5.0* H8 0.989 0.779 0.211 5.0* H9 1.059 0.714 0.147 5.0* H10 0.881 0.715 0.157 5.0* H11 0.826 0.069 -0.036 5.0* H12 0.721 0.167 0.002 5.0* H13 0.860 0.216 -0.041 5.0* 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 O1 0.081(1) 0.076(1) 0.047(1) -0.008(1) -0.006(1) -0.010(1) C1 0.050(2) 0.042(1) 0.059(2) 0.005(1) -0.008(1) -0.003(1) C2 0.056(2) 0.051(2) 0.058(2) 0.006(1) -0.003(2) -0.009(1) C3 0.041(1) 0.050(2) 0.048(1) -0.001(1) 0.004(1) -0.001(1) C4 0.057(2) 0.061(2) 0.043(1) -0.007(2) 0.005(1) 0.001(1) C5 0.070(2) 0.074(2) 0.048(2) 0.001(2) -0.008(2) 0.013(2) C6 0.064(2) 0.058(2) 0.059(2) 0.010(2) 0.001(2) 0.014(2) C7 0.047(1) 0.044(1) 0.050(2) 0.001(1) 0.006(1) 0.006(1) C8 0.038(1) 0.048(1) 0.052(1) -0.001(1) 0.002(1) 0.000(1) C9 0.046(1) 0.043(1) 0.068(2) 0.001(1) 0.009(2) 0.006(1) C10 0.068(2) 0.047(2) 0.094(2) -0.000(2) 0.008(2) 0.016(2) C11 0.112(3) 0.104(3) 0.043(2) -0.019(3) -0.008(2) -0.001(2) # 10. MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance #_geom_bond_publ_flag O1 C4 1.381(4) C6 C7 1.384(4) O1 C11 1.417(4) C6 H6 0.950(3) C1 C2 1.529(4) C7 C8 1.402(4) C1 H1 0.950(3) C7 C9 1.503(4) C1 H2 0.950(3) C8 H7 0.950(3) C2 C3 1.507(4) C9 C10 1.509(5) C2 H4 0.950(3) C10 H8 0.950(4) C2 H3 0.950(3) C10 H9 0.950(4) C3 C4 1.408(4) C10 H10 0.950(4) C3 C8 1.392(4) C11 H11 0.950(4) C4 C5 1.378(5) C11 H12 0.950(5) C5 C6 1.378(5) C11 H13 0.950(4) C5 H5 0.950(3) loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle #_geom_angle_publ_flag C4 O1 C11 117.9(3) C7 C6 H6 118.4(3) C2 C1 H1 110.0(3) C6 C7 C8 116.5(3) C2 C1 H2 108.6(3) C6 C7 C9 119.4(3) C8 C7 C9 124.1(3) O1 C11 H11 110.1(4) C1 C2 C3 112.9(2) C3 C8 C7 123.3(3) C1 C2 H4 107.9(3) C3 C8 H7 118.2(3) C1 C2 H3 109.2(3) C7 C8 H7 118.5(3) C3 C2 H4 108.3(3) C7 C9 C10 114.0(3) C3 C2 H3 109.0(3) C9 C10 H8 110.1(3) C9 C10 H9 108.4(3) O1 C11 H12 109.0(3) C2 C3 C4 121.4(3) C9 C10 H10 109.9(3) C2 C3 C8 121.3(3) O1 C11 H13 109.3(4) C4 C3 C8 117.0(3) O1 C4 C3 115.5(3) O1 C4 C5 124.0(3) C3 C4 C5 120.5(3) C4 C5 C6 120.2(3) C4 C5 H5 120.1(3) C6 C5 H5 119.7(3) C5 C6 C7 122.1(3) C5 C6 H6 119.5(3) data_11-acetyl-11-methyl-6,15-dimethoxy[4.1]metacyclophane _database_code_CSD 155636 #--------------------------------------------- _publ_contact_author_name 'Takehiko Yamato' _publ_contact_author_email yamatot@cc.saga-u.ac.jp _publ_contact_author_fax '+ 81(0)952/28-8591' _publ_contact_author_phone '+ 81(0)952/28-8679' _publ_contact_author_address ; Department of Applied Chemistry, Faculty of Science and Engineering, Saga University, Honjo-machi 1, Saga-shi, Saga 840-8502, Japan ; Cif-file #======================================================================= _audit_creation_date 05-10-00 _audit_creation_method from_MolEN_master_file_using_cif_in _audit_update_record ; ? ; # 1. SUBMISSION DETAILS _publ_contact_author ; Takehiko Yamato Department of Applied Chemistry, Faculty of Science and Engineering, Saga University, Honjo-machi 1, Saga-shi, Saga 840-8502, Japan ; _publ_contact_author_email yamatot@cc.saga-u.ac.jp _publ_contact_author_fax '+ 81(0)952/28-8591' _publ_contact_author_phone '+ 81(0)952/28-8679' _publ_requested_journal 'Journal of Chemical Society, Perkin Trans. 1' _publ_requested_coeditor_name ? # 2. 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_Cambridge 207 _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? # 3. TITLE AND AUTHOR LIST _publ_section_title ; Medium-sized cyclophanes. Part 58. Synthesis and conformational studies of [2.n]metacyclophan-1-enes and [n.1]metacyclophanes ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address 'Takehiko Yamato' ;Department of Applied Chemistry, Faculty of Science and Engineering, Saga University, Honjo-machi 1, Saga-shi, Saga 840-8502, Japan ; 'Koji Fujita' ;Department of Applied Chemistry, Faculty of Science and Engineering, Saga University, Honjo-machi 1, Saga-shi, Saga 840-8502, Japan ; 'Hirohisa Tsuzuki' ;Tohwa Institute for Science, Tohwa University, 1-1-1 Chikushigaoka, Minami-ku, Fukuoka-shi, Fukuoka 815-8510, Japan ; # 4. TEXT _publ_section_abstract ; ? ; _publ_section_comment ; ? ; _publ_section_experimental ; Backgrounds were obtained from analysis of the scan profile (Blessing, Coppens_& Becker, 1974) ; _publ_section_references ; Blessing, R.H., Coppens, P. & Becker, P. (1974). J. Appl. Cryst., 7, 488-492. Burla, M.C., Camalli, M., Cascarano, G.,Giacovazzo, C., Polidori, G., Spagna, R. &Viterbo, D. (1989). SIR. J. Appl. Cryst. 22, 389-393. Enraf-Nonius, CAD4 Operations Manual, Delft, 1977. Fair, C.K. (1990). MolEN, An Interactive Intelligent System for Crystal Structure Analysis, User Manual, Enraf - Nonius, Delft, The Netherlands. International Tables for X-Ray Crystallography, Vol. IV, The Kynoch Press, Birmingham, England, 1974 Johnson, C.K. (1976). ORTEP. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA. Zachariasen, W.H. (1963). Acta Crystallogr., 16, 1139-1144. ; _publ_section_figure_captions ; ? ; _publ_section_acknowledgements ; ? ; #data_11-acetyl-11-methyl-6,15-dimethoxy[4.1]metacyclophane # 5. CRYSTAL DATA _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_method ? _chemical_formula_sum 'C22 H26 O3' _chemical_formula_structural ? _chemical_formula_weight 338.45 _symmetry_cell_setting monoclinic _symmetry_space_group_name_h-m 'P21/c' _cell_length_a 14.8271(13) _cell_length_b 12.8995(10) _cell_length_c 9.5892(5) _cell_angle_alpha 90 _cell_angle_beta 95.9810(57) _cell_angle_gamma 90 _cell_volume 1824.1(1) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 28.97 _cell_measurement_theta_max 30.016 _cell_formula_units_z 4 _exptl_crystal_density_diffrn 1.066 _exptl_crystal_density_meas ? _diffrn_radiation_type 'Cu KYa' _diffrn_radiation_wavelength 1.54184Y%A _exptl_absorpt_coefficient_mu 6.024 _cell_measurement_temperature 295 _exptl_crystal_F_000 728 # 6. DATA COLLECTION _diffrn_ambient_temperature 295 _diffrn_measurement_device Enraf_Nonius_CAD4 _diffrn_measurement_method Yw/2Yq _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.0000 _exptl_absorpt_correction_T_max 0.0000 _diffrn_reflns_number 4061 _reflns_number_total 3665 _reflns_number_observed 2489 _reflns_observed_criterion >3.0(Ys) _diffrn_reflns_av_R_equivalents 0.025 _diffrn_reflns_theta_min 2.0 _diffrn_reflns_theta_max 75.0 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_max 12 _diffrn_standards_number 5 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% ? # 7. REFINEMENT DATA _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_R_factor_all 0.083 _refine_ls_wR_factor_all ? _refine_ls_wR_factor_obs 0.121 _refine_ls_hydrogen_treatment riding _refine_ls_number_reflns 3665 _refine_ls_number_parameters 227 _refine_ls_number_restraints 132 _refine_ls_goodness_of_fit_all ? _refine_ls_goodness_of_fit_obs 3.499 _refine_ls_weighting_scheme 'calc w=4Fo^2^/ (Ys^2^(Fo^2^) + 0.0016 Fo^4^)' _refine_ls_shift/esd_max 0.01 _refine_diff_density_max 0.897 _refine_diff_density_min -0.511 _refine_ls_extinction_method isotropic_(Zachariasen,_1963) _refine_ls_extinction_coef 4.95E-07 _atom_type_scat_source International_Tables_for_Xray_Crystallography # 8. COMPUTING DATA _computing_data_collection CAD4_(Enraf-Nonius,_1977) _computing_cell_refinement CAD4_(Enraf-Nonius,_1977) _computing_data_reduction PROCESS_MolEN_(Fair,_1990) _computing_structure_solution Direct_methods_(SIR,_Burla_et_al.,_1989) _computing_structure_refinement LSFM_MolEN_(Fair,_1990) _computing_molecular_graphics ORTEP_(Johnson,_1976) _computing_publication_material CIF_IN_MolEN_(Fair,_1990) _refine_ls_abs_structure_details ; ? ; # 9. 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_thermal_displace_type #_atom_site_calc_flag O1 0.9205(3) 0.1414(2) 0.0458(1) 5.38(5) C1 1.0835(4) 0.0822(3) 0.2378(2) 3.98(6) C2 1.1008(4) 0.1095(3) 0.1622(2) 4.33(7) C3 1.0340(3) 0.2385(3) 0.1417(2) 3.66(6) C4 0.9319(4) 0.2498(3) 0.0865(2) 4.23(6) C5 0.8512(4) 0.3631(3) 0.0756(2) 5.03(7) C6 0.8713(4) 0.4674(3) 0.1182(2) 4.76(7) C7 0.9757(3) 0.4649(3) 0.1713(2) 3.71(6) C8 1.0588(3) 0.3495(3) 0.1803(2) 3.64(6) C9 0.9905(4) 0.5813(3) 0.2165(2) 4.11(6) C10 0.9784(4) 0.7092(3) 0.1797(2) 5.50(8) C11 0.8243(6) 0.1490(4) -0.0121(2) 6.8(1) H1 1.126 0.000 0.248 5.0* H2 1.137 0.147 0.262 5.0* H3 1.207 0.107 0.151 5.0* H4 1.047 0.043 0.138 5.0* H5 0.782 0.370 0.038 5.0* H6 0.811 0.543 0.112 5.0* H7 1.136 0.347 0.214 5.0* H8 0.989 0.779 0.211 5.0* H9 1.059 0.714 0.147 5.0* H10 0.881 0.715 0.157 5.0* H11 0.826 0.069 -0.036 5.0* H12 0.721 0.167 0.002 5.0* H13 0.860 0.216 -0.041 5.0* 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 O1 0.081(1) 0.076(1) 0.047(1) -0.008(1) -0.006(1) -0.010(1) C1 0.050(2) 0.042(1) 0.059(2) 0.005(1) -0.008(1) -0.003(1) C2 0.056(2) 0.051(2) 0.058(2) 0.006(1) -0.003(2) -0.009(1) C3 0.041(1) 0.050(2) 0.048(1) -0.001(1) 0.004(1) -0.001(1) C4 0.057(2) 0.061(2) 0.043(1) -0.007(2) 0.005(1) 0.001(1) C5 0.070(2) 0.074(2) 0.048(2) 0.001(2) -0.008(2) 0.013(2) C6 0.064(2) 0.058(2) 0.059(2) 0.010(2) 0.001(2) 0.014(2) C7 0.047(1) 0.044(1) 0.050(2) 0.001(1) 0.006(1) 0.006(1) C8 0.038(1) 0.048(1) 0.052(1) -0.001(1) 0.002(1) 0.000(1) C9 0.046(1) 0.043(1) 0.068(2) 0.001(1) 0.009(2) 0.006(1) C10 0.068(2) 0.047(2) 0.094(2) -0.000(2) 0.008(2) 0.016(2) C11 0.112(3) 0.104(3) 0.043(2) -0.019(3) -0.008(2) -0.001(2) # 10. MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance #_geom_bond_publ_flag O1 C4 1.381(4) C6 C7 1.384(4) O1 C11 1.417(4) C6 H6 0.950(3) C1 C2 1.529(4) C7 C8 1.402(4) C1 H1 0.950(3) C7 C9 1.503(4) C1 H2 0.950(3) C8 H7 0.950(3) C2 C3 1.507(4) C9 C10 1.509(5) C2 H4 0.950(3) C10 H8 0.950(4) C2 H3 0.950(3) C10 H9 0.950(4) C3 C4 1.408(4) C10 H10 0.950(4) C3 C8 1.392(4) C11 H11 0.950(4) C4 C5 1.378(5) C11 H12 0.950(5) C5 C6 1.378(5) C11 H13 0.950(4) C5 H5 0.950(3) loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle #_geom_angle_publ_flag C4 O1 C11 117.9(3) C7 C6 H6 118.4(3) C2 C1 H1 110.0(3) C6 C7 C8 116.5(3) C2 C1 H2 108.6(3) C6 C7 C9 119.4(3) C8 C7 C9 124.1(3) O1 C11 H11 110.1(4) C1 C2 C3 112.9(2) C3 C8 C7 123.3(3) C1 C2 H4 107.9(3) C3 C8 H7 118.2(3) C1 C2 H3 109.2(3) C7 C8 H7 118.5(3) C3 C2 H4 108.3(3) C7 C9 C10 114.0(3) C3 C2 H3 109.0(3) C9 C10 H8 110.1(3) C9 C10 H9 108.4(3) O1 C11 H12 109.0(3) C2 C3 C4 121.4(3) C9 C10 H10 109.9(3) C2 C3 C8 121.3(3) O1 C11 H13 109.3(4) C4 C3 C8 117.0(3) O1 C4 C3 115.5(3) O1 C4 C5 124.0(3) C3 C4 C5 120.5(3) C4 C5 C6 120.2(3) C4 C5 H5 120.1(3) C6 C5 H5 119.7(3) C5 C6 C7 122.1(3) C5 C6 H6 119.5(3)