# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2001 # CCDC Number: 440/248 data_1 ---------------------------------------------- Cif-file #======================================================================= data_[2.1.1]orthocyclophane #======================================================================= _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 New Journal of Chemistry _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_ASTM ? _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, 55: Synthesis and conformational studies of [2.1.1]orthocyclophanes ; # 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; 'Naozumi Sakaue' Department of Applied Chemistry, Faculty of Science and Engineering, Saga University, Honjo-machi 1, Saga-shi, Saga 840-8502, Japan 'Kan Tanaka' Department of Industrial Chemistry, Faculty of Science and Engineering, Tohwa University, 1-1-1 Chikushigaoka, Minami-ku, Fukuoka-shi, Fukuoka 815-8510, 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_[2.1.1]orthocyclophane # 5. CRYSTAL DATA _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_method ? _chemical_formula_sum 'C22 H20' _chemical_formula_structural ? _chemical_formula_weight 284.40 _symmetry_cell_setting triclinic _symmetry_space_group_name_h-m 'P-1 (No. 2)' _cell_length_a 10.2590 (5) _cell_length_b 14.7368 (7) _cell_length_c 5.1617 (4) _cell_angle_alpha 93.601 (5) _cell_angle_beta 111.643 (5) _cell_angle_gamma 85.992 (4) _cell_volume 772.88 (8) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 34.96 _cell_measurement_theta_max 36.83 _cell_formula_units_z 2 _exptl_crystal_density_diffrn 1.222 _exptl_crystal_density_meas ? _diffrn_radiation_type 'Cu KYa' _diffrn_radiation_wavelength 1.54184Y%A _exptl_absorpt_coefficient_mu 4.82 _cell_measurement_temperature 298 _exptl_crystal_F_000 304 # 6. DATA COLLECTION _diffrn_ambient_temperature 298 _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 3556 _reflns_number_total 3187 _reflns_number_observed 2992 _reflns_observed_criterion >3.0(Ys) _diffrn_reflns_av_R_equivalents 0.015 _diffrn_reflns_theta_min 3.0 _diffrn_reflns_theta_max 74.9 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_max 6 _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 2.4 # 7. REFINEMENT DATA _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_R_factor_all 0.046 _refine_ls_wR_factor_all ? _refine_ls_wR_factor_obs 0.081 _refine_ls_hydrogen_treatment riding _refine_ls_number_reflns 2657 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_goodness_of_fit_all ? _refine_ls_goodness_of_fit_obs 3.05 _refine_ls_weighting_scheme 'calc w=4Fo^2^/ (Ys^2^(Fo^2^) + 0.0016 Fo^4^)' _refine_ls_shift/esd_max 0.03 _refine_diff_density_max 0.169(8) _refine_diff_density_min -0.150(8) _refine_ls_extinction_method isotropic_(Zachariasen,_1963) _refine_ls_extinction_coef 2.5E-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 C1 -0.4412(1) 0.2954(1) 0.5518(4) 4.65(3) C2 -0.4100(2) 0.2040(1) 0.3996(3) 4.90(3) C3 -0.3304(2) 0.1326(1) 0.5574(3) 4.15(3) C4 -0.3997(2) 0.0747(1) 0.6903(4) 5.18(4) C5 -0.3366(2) 0.0076(1) 0.8432(4) 5.66(4) C6 -0.2025(2) -0.0041(1) 0.8629(4) 5.19(4) C7 -0.1316(2) 0.0529(1) 0.7330(3) 4.53(3) C8 -0.1935(1) 0.12200(9) 0.5839(3) 3.79(3) C9 -0.1074(1) 0.18309(9) 0.4595(3) 4.00(3) C10 -0.0024(1) 0.22302(9) 0.6526(3) 3.56(2) C11 0.1293(2) 0.1962(1) 0.6409(3) 4.72(3) C12 0.2264(2) 0.2299(1) 0.8225(4) 5.45(4) C13 0.1926(2) 0.2910(1) 1.0197(4) 5.31(3) C14 0.0623(2) 0.3191(1) 1.0339(3) 4.41(3) C15 -0.0365(1) 0.28690(8) 0.8528(2) 3.40(2) C16 -0.1767(1) 0.32116(9) 0.8748(3) 3.55(2) C17 -0.2328(1) 0.38358(9) 0.6616(3) 3.46(2) C18 -0.1628(2) 0.45762(9) 0.6154(3) 4.09(3) C19 -0.2073(2) 0.5180(1) 0.4268(3) 4.64(3) C20 -0.3252(2) 0.5054(1) 0.2796(3) 4.88(3) C21 -0.3965(2) 0.4335(1) 0.3233(3) 4.71(3) C22 -0.3543(1) 0.37153(9) 0.5146(3) 3.84(3) H1 -0.432 0.284 0.735 5.0* H2 -0.530 0.315 0.501 5.0* H3 -0.361 0.217 0.261 5.0* H4 -0.490 0.180 0.330 5.0* H5 -0.493 0.081 0.675 5.0* H6 -0.385 -0.030 0.935 5.0* H7 -0.158 -0.051 0.964 5.0* H8 -0.039 0.044 0.747 5.0* H9 -0.161 0.232 0.384 5.0* H10 -0.066 0.148 0.327 5.0* H11 0.154 0.154 0.505 5.0* H12 0.316 0.210 0.810 5.0* H13 0.259 0.314 1.144 5.0* H14 0.039 0.361 1.171 5.0* H15 -0.181 0.353 1.039 5.0* H16 -0.229 0.270 0.865 5.0* H17 -0.081 0.466 0.716 5.0* H18 -0.158 0.568 0.401 5.0* H19 -0.357 0.546 0.148 5.0* H20 -0.477 0.425 0.220 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 C1 0.0414(6) 0.0630(8) 0.0723(9) -0.0027(6) 0.0015(7) 0.0102(7) C2 0.0567(8) 0.0631(8) 0.0640(9) -0.0130(7) -0.0114(7) 0.0049(7) C3 0.0595(7) 0.0477(7) 0.0502(7) -0.0115(6) 0.0018(6) -0.0024(6) C4 0.0599(8) 0.0584(8) 0.080(1) -0.0156(7) 0.0078(8) 0.0051(8) C5 0.082(1) 0.0602(8) 0.078(1) -0.0233(7) 0.0152(8) 0.0124(7) C6 0.079(1) 0.0506(7) 0.0681(9) -0.0107(7) 0.0020(8) 0.0129(7) C7 0.0630(8) 0.0477(7) 0.0616(8) -0.0082(6) 0.0015(7) 0.0058(6) C8 0.0592(7) 0.0431(6) 0.0416(6) -0.0100(5) 0.0038(6) -0.0024(5) C9 0.0619(7) 0.0500(7) 0.0413(6) -0.0074(6) 0.0099(6) 0.0010(5) C10 0.0490(6) 0.0425(6) 0.0462(6) -0.0059(5) 0.0095(5) 0.0100(5) C11 0.0588(7) 0.0515(7) 0.0726(9) -0.0004(6) 0.0198(7) 0.0124(7) C12 0.0438(7) 0.0691(8) 0.097(1) -0.0061(7) 0.0036(7) 0.0317(8) C13 0.0560(8) 0.0713(9) 0.0745(9) -0.0179(7) -0.0135(7) 0.0239(7) C14 0.0616(8) 0.0552(7) 0.0501(7) -0.0132(6) -0.0079(6) 0.0114(6) C15 0.0489(6) 0.0413(5) 0.0397(5) -0.0063(5) 0.0012(5) 0.0103(5) C16 0.0519(6) 0.0457(6) 0.0375(5) -0.0031(5) 0.0057(5) 0.0035(5) C17 0.0485(6) 0.0424(6) 0.0399(6) 0.0021(5) 0.0063(5) 0.0013(5) C18 0.0562(7) 0.0473(7) 0.0513(7) -0.0036(6) 0.0020(6) 0.0029(6) C19 0.0700(9) 0.0465(7) 0.0606(8) -0.0005(7) 0.0088(7) 0.0106(6) C20 0.0718(9) 0.0552(7) 0.0571(8) 0.0123(7) 0.0043(7) 0.0159(6) C21 0.0519(7) 0.0637(8) 0.0600(8) 0.0094(7) -0.0031(7) 0.0078(7) C22 0.0446(6) 0.0492(7) 0.0514(7) 0.0040(6) 0.0058(6) 0.0030(6) # 10. MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C1 C2 1.547(2) C10 C15 1.409(2) C1 C22 1.515(2) C11 C12 1.389(2) C1 H1 0.962(2) C11 H11 0.950(2) C1 H2 0.949(1) C12 C13 1.372(3) C2 C3 1.511(2) C12 H12 0.950(2) C2 H3 0.950(2) C13 C14 1.380(2) C2 H4 0.950(2) C13 H13 0.950(2) C3 C4 1.402(2) C14 C15 1.392(2) C3 C8 1.395(2) C14 H14 0.950(1) C4 C5 1.386(2) C15 C16 1.504(2) C4 H5 0.950(2) C16 C17 1.519(2) C5 C6 1.367(3) C16 H15 0.950(1) C5 H6 0.950(2) C16 H16 0.950(1) C6 C7 1.394(3) C17 C18 1.393(2) C6 H7 0.950(2) C17 C22 1.405(2) C7 C8 1.392(2) C18 C19 1.381(2) C7 H8 0.950(2) C18 H17 0.950(1) C8 C9 1.519(2) C19 C20 1.376(2) C9 C10 1.513(2) C19 H18 0.950(2) C9 H9 0.950(1) C20 C21 1.371(2) C9 H10 0.950(1) C20 H19 0.950(2) C10 C11 1.388(2) C21 C22 1.401(2) C21 H20 0.950(2) 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 C2 C1 C22 115.6(1) C5 C6 H7 120.3(2) C2 C1 H1 107.7(1) C7 C6 H7 120.3(2) C2 C1 H2 108.4(1) C6 C7 C8 121.8(2) C22 C1 H1 107.9(1) C6 C7 H8 119.2(2) C22 C1 H2 108.6(1) C8 C7 H8 119.0(2) C3 C8 C7 119.0(1) C17 C22 C21 117.8(1) C1 C2 C3 115.2(1) C3 C8 C9 123.1(1) C1 C2 H3 107.5(1) C7 C8 C9 117.8(1) C1 C2 H4 108.6(1) C8 C9 C10 112.8(1) C3 C2 H3 107.7(1) C8 C9 H9 108.7(1) C3 C2 H4 108.3(1) C8 C9 H10 108.5(1) C10 C9 H9 108.6(1) C1 C22 C17 123.5(1) C2 C3 C4 117.2(1) C10 C9 H10 108.6(1) C2 C3 C8 124.5(1) C22 C21 H20 118.3(2) C4 C3 C8 118.2(1) C9 C10 C11 121.0(1) C3 C4 C5 122.1(2) C9 C10 C15 120.6(1) C3 C4 H5 119.2(2) C11 C10 C15 118.4(1) C5 C4 H5 118.7(2) C10 C11 C12 121.6(1) C4 C5 C6 119.5(2) C10 C11 H11 119.3(1) C4 C5 H6 120.9(2) C12 C11 H11 119.1(2) C6 C5 H6 119.7(2) C11 C12 C13 119.8(1) C5 C6 C7 119.4(2) C11 C12 H12 119.6(2) C13 C12 H12 120.5(2) C16 C17 C22 122.8(1) C12 C13 C14 119.5(1) C18 C17 C22 118.6(1) C12 C13 H13 119.9(2) C17 C18 C19 122.3(1) C14 C13 H13 120.5(2) C17 C18 H17 118.7(1) C13 C14 C15 121.6(1) C19 C18 H17 119.0(1) C13 C14 H14 119.5(1) C18 C19 C20 119.2(2) C15 C14 H14 118.9(1) C18 C19 H18 120.5(2) C10 C15 C14 119.0(1) C20 C19 H18 120.3(2) C10 C15 C16 121.6(1) C19 C20 C21 119.6(1) C14 C15 C16 119.4(1) C19 C20 H19 120.3(2) C15 C16 C17 113.8(1) C21 C20 H19 120.1(2) C15 C16 H15 108.5(1) C20 C21 C22 122.5(1) C15 C16 H16 108.1(1) C20 C21 H20 119.1(2) C17 C16 H15 108.7(1) C17 C16 H16 108.2(1) C1 C22 C21 118.6(1) C16 C17 C18 118.6(1)