# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2004 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 #============================================================================== _publ_contact_author_name 'Prof Dietmar Kuck' _publ_contact_author_address ; Fakultat fur Chemie Universitat Bielefeld Universitastrasse 25 Bielefeld D-33615 GERMANY ; _publ_contact_author_email DIETMAR.KUCK@UNI-BIELEFELD.DE _publ_section_title ; Methoxy-substituted centrohexaindanes through the fenestrane route ; # 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 J.Tellenbroker ; Fakultat f. Chemie Universitat Bielefeld 33615 Bielefeld Germany ; D.Barth ; Fakultat f. Chemie Universitat Bielefeld 33615 Bielefeld Germany ; B.Neumann ; Fakultat f. Chemie Universitat Bielefeld 33615 Bielefeld Germany ; H.-G.Stammler ; Fakultat f. Chemie Universitat Bielefeld 33615 Bielefeld Germany ; D.Kuck ; Fakultat f. Chemie Universitat Bielefeld 33615 Bielefeld Germany ; #========================================================================= data_compound7 _database_code_depnum_ccdc_archive 'CCDC 250182' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C45 H32 O4 . H2 O . C H3 OH' _chemical_formula_sum 'C46 H38 O6' _chemical_formula_weight 686.76 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 17.357(8) _cell_length_b 13.487(5) _cell_length_c 14.830(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3472(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 36 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 8.4 _exptl_crystal_description octahedral _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.314 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1448 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens P2(1) diffractometer' _diffrn_measurement_method Wyckoff-scan _diffrn_refln_scan_width 2.4 _diffrn_standards_number 2 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3185 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0646 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3185 _reflns_number_gt 1971 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'P3 (1989)' _computing_cell_refinement 'P3 (1989)' _computing_data_reduction 'SHELXTL-PLUS (1990)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.1005P)^2^+5.0304P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3185 _refine_ls_number_parameters 251 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1294 _refine_ls_R_factor_gt 0.0753 _refine_ls_wR_factor_ref 0.2126 _refine_ls_wR_factor_gt 0.1787 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.0212(2) 0.2500 0.7095(3) 0.0323(10) Uani 1 d S . . O2 O 0.1606(2) 0.2500 0.7684(2) 0.0327(10) Uani 1 d S . . O3 O 0.35137(16) 0.1543(2) -0.00610(17) 0.0305(7) Uani 1 d . . . C1 C 0.2081(3) 0.2500 0.3595(4) 0.0217(12) Uani 1 d S . . C2 C 0.1211(3) 0.2500 0.3865(3) 0.0217(12) Uani 1 d S . . C3 C 0.1241(3) 0.2500 0.4908(3) 0.0228(12) Uani 1 d S . . C4 C 0.1997(3) 0.2500 0.5227(4) 0.0218(12) Uani 1 d S . . C5 C 0.2590(3) 0.2500 0.4464(3) 0.0224(12) Uani 1 d S . . C6 C 0.3038(2) 0.1534(3) 0.4386(2) 0.0228(9) Uani 1 d . . . C7 C 0.2844(2) 0.1007(3) 0.3603(2) 0.0229(9) Uani 1 d . . . C8 C 0.2254(2) 0.1561(3) 0.3027(2) 0.0206(8) Uani 1 d . . . C9 C 0.1473(2) 0.1062(3) 0.2930(2) 0.0236(9) Uani 1 d . . . C10 C 0.0899(2) 0.1561(3) 0.3431(2) 0.0226(9) Uani 1 d . . . C11 C 0.0625(3) 0.2500 0.5508(3) 0.0255(13) Uani 1 d S . . H11 H 0.0111 0.2500 0.5289 0.031 Uiso 1 calc SR . . C12 C 0.0766(3) 0.2500 0.6436(4) 0.0258(13) Uani 1 d S . . C13 C 0.1537(3) 0.2500 0.6760(4) 0.0259(13) Uani 1 d S . . C14 C 0.2147(3) 0.2500 0.6158(4) 0.0255(13) Uani 1 d S . . H14 H 0.2663 0.2500 0.6373 0.031 Uiso 1 calc SR . . C15 C 0.3568(2) 0.1137(3) 0.4995(3) 0.0319(10) Uani 1 d . . . H15 H 0.3708 0.1495 0.5521 0.038 Uiso 1 calc R . . C16 C 0.3892(2) 0.0204(4) 0.4821(3) 0.0373(11) Uani 1 d . . . H16 H 0.4248 -0.0076 0.5236 0.045 Uiso 1 calc R . . C17 C 0.3696(3) -0.0311(3) 0.4046(3) 0.0378(11) Uani 1 d . . . H17 H 0.3921 -0.0941 0.3933 0.045 Uiso 1 calc R . . C18 C 0.3172(2) 0.0084(3) 0.3429(3) 0.0287(9) Uani 1 d . . . H18 H 0.3041 -0.0272 0.2898 0.034 Uiso 1 calc R . . C19 C 0.1284(2) 0.0234(3) 0.2414(3) 0.0281(9) Uani 1 d . . . H19 H 0.1668 -0.0096 0.2070 0.034 Uiso 1 calc R . . C20 C 0.0527(2) -0.0107(3) 0.2406(3) 0.0325(10) Uani 1 d . . . H20 H 0.0392 -0.0667 0.2051 0.039 Uiso 1 calc R . . C21 C -0.0033(2) 0.0371(3) 0.2920(3) 0.0359(11) Uani 1 d . . . H21 H -0.0545 0.0123 0.2920 0.043 Uiso 1 calc R . . C22 C 0.0145(2) 0.1208(3) 0.3435(3) 0.0290(9) Uani 1 d . . . H22 H -0.0241 0.1530 0.3781 0.035 Uiso 1 calc R . . C23 C -0.0573(3) 0.2500 0.6804(4) 0.0318(14) Uani 1 d S . . H23A H -0.0913 0.2500 0.7331 0.048 Uiso 1 calc SR . . H23B H -0.0672 0.1907 0.6440 0.048 Uiso 0.50 calc PR . . H23C H -0.0672 0.3093 0.6440 0.048 Uiso 0.50 calc PR . . C24 C 0.2366(3) 0.2500 0.8058(4) 0.0304(14) Uani 1 d S . . H24A H 0.2334 0.2500 0.8718 0.046 Uiso 1 calc SR . . H24B H 0.2643 0.3093 0.7856 0.046 Uiso 0.50 calc PR . . H24C H 0.2643 0.1907 0.7856 0.046 Uiso 0.50 calc PR . . C25 C 0.2583(2) 0.1988(3) 0.2150(2) 0.0228(8) Uani 1 d . . . C26 C 0.2880(2) 0.1455(3) 0.1414(2) 0.0240(9) Uani 1 d . . . H26 H 0.2872 0.0751 0.1413 0.029 Uiso 1 calc R . . C27 C 0.3185(2) 0.1973(3) 0.0685(2) 0.0239(9) Uani 1 d . . . C28 C 0.3528(3) 0.0476(3) -0.0086(3) 0.0353(11) Uani 1 d . . . H28A H 0.3824 0.0225 0.0429 0.053 Uiso 1 calc R . . H28B H 0.3770 0.0254 -0.0648 0.053 Uiso 1 calc R . . H28C H 0.3000 0.0221 -0.0055 0.053 Uiso 1 calc R . . O4 O -0.0035(3) 0.2500 0.8932(4) 0.0684(16) Uiso 1 d S . . O5 O 0.0879(6) 0.2500 1.0456(8) 0.154(4) Uiso 1 d S . . C29 C 0.0338(7) 0.2500 1.1195(8) 0.100(4) Uiso 1 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0184(19) 0.056(3) 0.022(2) 0.000 0.0043(17) 0.000 O2 0.023(2) 0.057(3) 0.018(2) 0.000 -0.0029(17) 0.000 O3 0.0400(16) 0.0296(16) 0.0218(14) -0.0056(12) 0.0089(12) -0.0010(13) C1 0.019(3) 0.024(3) 0.023(3) 0.000 0.000(2) 0.000 C2 0.017(3) 0.030(3) 0.018(3) 0.000 0.003(2) 0.000 C3 0.019(3) 0.028(3) 0.022(3) 0.000 0.001(2) 0.000 C4 0.020(3) 0.025(3) 0.020(3) 0.000 0.004(2) 0.000 C5 0.020(3) 0.027(3) 0.020(3) 0.000 -0.001(2) 0.000 C6 0.0174(18) 0.026(2) 0.025(2) 0.0027(17) 0.0050(15) -0.0027(16) C7 0.0213(19) 0.025(2) 0.0224(19) 0.0039(17) 0.0069(16) -0.0012(17) C8 0.0217(19) 0.022(2) 0.0181(18) -0.0001(16) 0.0014(15) 0.0002(16) C9 0.026(2) 0.028(2) 0.0173(17) 0.0066(17) -0.0022(16) -0.0025(17) C10 0.0244(19) 0.027(2) 0.0168(17) 0.0044(17) -0.0002(16) -0.0014(17) C11 0.023(3) 0.033(3) 0.020(3) 0.000 -0.005(2) 0.000 C12 0.022(3) 0.034(3) 0.022(3) 0.000 0.004(2) 0.000 C13 0.029(3) 0.030(3) 0.019(3) 0.000 0.002(2) 0.000 C14 0.019(3) 0.034(3) 0.023(3) 0.000 -0.002(2) 0.000 C15 0.024(2) 0.038(3) 0.033(2) 0.000(2) -0.0021(18) 0.0015(19) C16 0.031(2) 0.040(3) 0.041(2) 0.006(2) -0.006(2) 0.012(2) C17 0.035(2) 0.031(2) 0.047(3) 0.002(2) 0.009(2) 0.012(2) C18 0.028(2) 0.029(2) 0.029(2) -0.0014(18) 0.0028(18) 0.0027(18) C19 0.033(2) 0.028(2) 0.023(2) -0.0006(18) 0.0025(17) -0.0014(19) C20 0.039(2) 0.032(2) 0.026(2) -0.0025(18) -0.0029(19) -0.011(2) C21 0.027(2) 0.045(3) 0.035(2) 0.002(2) -0.0021(19) -0.013(2) C22 0.021(2) 0.040(3) 0.025(2) -0.0005(19) 0.0023(17) -0.0028(19) C23 0.020(3) 0.049(4) 0.027(3) 0.000 0.001(2) 0.000 C24 0.027(3) 0.041(4) 0.024(3) 0.000 -0.007(3) 0.000 C25 0.0223(19) 0.025(2) 0.0212(18) 0.0002(17) 0.0024(16) -0.0017(17) C26 0.0249(19) 0.022(2) 0.025(2) -0.0028(17) 0.0005(16) -0.0003(17) C27 0.0228(19) 0.030(2) 0.0185(18) -0.0032(17) 0.0001(16) 0.0013(17) C28 0.042(3) 0.035(3) 0.029(2) -0.0108(19) 0.007(2) -0.003(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C12 1.370(6) . Y O1 C23 1.428(7) . Y O2 C13 1.375(6) . Y O2 C24 1.432(7) . Y O3 C27 1.374(4) . Y O3 C28 1.440(5) . Y C1 C8 1.550(5) 7_565 Y C1 C8 1.550(5) . Y C1 C5 1.562(7) . Y C1 C2 1.563(7) . Y C2 C10 1.521(5) . Y C2 C10 1.521(5) 7_565 Y C2 C3 1.546(7) . Y C3 C11 1.392(7) . Y C3 C4 1.395(7) . Y C4 C14 1.405(8) . Y C4 C5 1.529(7) . Y C5 C6 1.522(5) 7_565 Y C5 C6 1.522(5) . Y C6 C15 1.395(5) . Y C6 C7 1.402(5) . Y C7 C18 1.393(5) . Y C7 C8 1.528(5) . Y C8 C9 1.521(5) . Y C8 C25 1.532(5) . Y C9 C19 1.393(6) . Y C9 C10 1.414(5) . Y C10 C22 1.392(5) . Y C11 C12 1.397(7) . Y C12 C13 1.423(8) . Y C13 C14 1.384(8) . Y C15 C16 1.402(6) . Y C16 C17 1.385(6) . Y C17 C18 1.395(6) . Y C19 C20 1.391(6) . Y C20 C21 1.393(6) . Y C21 C22 1.398(6) . Y C25 C25 1.382(8) 7_565 Y C25 C26 1.404(5) . Y C26 C27 1.391(5) . Y C27 C27 1.422(8) 7_565 Y O5 C29 1.443(14) . Y 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_3 _geom_angle_publ_flag C12 O1 C23 117.0(4) . . Y C13 O2 C24 117.8(4) . . Y C27 O3 C28 116.7(3) . . Y C8 C1 C8 109.6(4) 7_565 . Y C8 C1 C5 109.8(3) 7_565 . Y C8 C1 C5 109.8(3) . . Y C8 C1 C2 109.1(3) 7_565 . Y C8 C1 C2 109.1(3) . . Y C5 C1 C2 109.5(4) . . Y C10 C2 C10 112.7(4) . 7_565 Y C10 C2 C3 115.8(3) . . Y C10 C2 C3 115.8(3) 7_565 . Y C10 C2 C1 103.7(3) . . Y C10 C2 C1 103.7(3) 7_565 . Y C3 C2 C1 103.0(4) . . Y C11 C3 C4 120.4(5) . . Y C11 C3 C2 127.9(5) . . Y C4 C3 C2 111.7(5) . . Y C3 C4 C14 120.5(5) . . Y C3 C4 C5 112.5(5) . . Y C14 C4 C5 127.0(5) . . Y C6 C5 C6 117.8(4) 7_565 . Y C6 C5 C4 113.6(3) 7_565 . Y C6 C5 C4 113.6(3) . . Y C6 C5 C1 103.1(3) 7_565 . Y C6 C5 C1 103.1(3) . . Y C4 C5 C1 103.3(4) . . Y C15 C6 C7 120.0(4) . . Y C15 C6 C5 128.1(4) . . Y C7 C6 C5 111.9(3) . . Y C18 C7 C6 120.5(4) . . Y C18 C7 C8 127.4(4) . . Y C6 C7 C8 112.1(3) . . Y C9 C8 C7 115.7(3) . . Y C9 C8 C25 114.7(3) . . Y C7 C8 C25 114.1(3) . . Y C9 C8 C1 103.9(3) . . Y C7 C8 C1 103.0(3) . . Y C25 C8 C1 103.1(3) . . Y C19 C9 C10 120.3(4) . . Y C19 C9 C8 128.1(3) . . Y C10 C9 C8 111.6(3) . . Y C22 C10 C9 120.1(4) . . Y C22 C10 C2 128.2(4) . . Y C9 C10 C2 111.6(3) . . Y C3 C11 C12 119.7(5) . . Y O1 C12 C11 125.4(5) . . Y O1 C12 C13 114.8(5) . . Y C11 C12 C13 119.8(5) . . Y O2 C13 C14 125.2(5) . . Y O2 C13 C12 114.6(5) . . Y C14 C13 C12 120.2(5) . . Y C13 C14 C4 119.4(5) . . Y C6 C15 C16 119.3(4) . . Y C17 C16 C15 120.3(4) . . Y C16 C17 C18 120.8(4) . . Y C7 C18 C17 119.1(4) . . Y C20 C19 C9 119.5(4) . . Y C19 C20 C21 120.1(4) . . Y C20 C21 C22 121.2(4) . . Y C10 C22 C21 118.8(4) . . Y C25 C25 C26 120.8(2) 7_565 . Y C25 C25 C8 112.0(2) 7_565 . Y C26 C25 C8 127.2(3) . . Y C27 C26 C25 119.1(4) . . Y O3 C27 C26 124.9(4) . . Y O3 C27 C27 115.0(2) . 7_565 Y C26 C27 C27 120.1(2) . 7_565 Y _diffrn_measured_fraction_theta_max 0.932 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.932 _refine_diff_density_max 1.207 _refine_diff_density_min -0.576 _refine_diff_density_rms 0.074