# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2002 data_global _audit_creation_method SHELXL-97 _chemical_name_systematic ; trans-1-(1-Benzocycloheptenyliden)benzocycloheptene ; #------------------------------------------------------------------------------ # SUBMISSION DETAILS _journal_coden_Cambridge 188 loop_ _publ_author_name 'Oelgemoeller, Michael' 'Brem, Bernhard' 'Frank, Rudolf' 'Hertkorn, Norbert' 'Hesek, D.' 'Inoue, Yoshihisa' 'Lemmen, Peter' 'Lenoir, Dieter' 'Lex, Johann' 'Schneider, Siegfried' _publ_contact_author_name 'Dr Michael Oelgemoeller' _publ_contact_author_address ; Chemical Research Department Nihon Bayer Agrochem K.K. 9511-4 Yuki Yuki-City Ibaraki 307-0001 JAPAN ; _publ_requested_journal 'J. Chem. Soc, Perkin Trans. 2' _publ_requested_coeditor_name ? _publ_contact_author_phone '+49 89 318 72960' _publ_contact_author_fax '+49 89 318 73371' _publ_contact_author_email 'MICHAEL.OELGEMOELLER.MO@BAYER.CO.JP' _publ_section_title ; Cyclic trans-Stilbenes: Synthesis, Structural and Spectroscopic Characterization, Photophysical and Photochemical Properties ; data_structure_7 _database_code_CSD 182507 _publ_section_exptl_refinement ? _chemical_name_common 'japoe09' _chemical_melting_point '179-180 deg' _chemical_formula_moiety ? _chemical_formula_sum 'C22 H24' _chemical_formula_weight 288.41 #------------------------------------------------------------------------------ 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' #------------------------------------------------------------------------------ _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n #------------------------------------------------------------------------------ loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, -z-1/2' #------------------------------------------------------------------------------ _cell_length_a 10.726(1) _cell_length_b 7.282(1) _cell_length_c 10.756(1) _cell_angle_alpha 90.00 _cell_angle_beta 106.29(1) _cell_angle_gamma 90.00 _cell_volume 806.39(15) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1748 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 27.00 #------------------------------------------------------------------------------ _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.188 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 0.066 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; 'grown from n-hexane' ; #------------------------------------------------------------------------------ _diffrn_ambient_temperature 293(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_type 'nonius KappaCCD' _diffrn_measurement_method Phi/Omega-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3305 _diffrn_reflns_av_R_equivalents 0.0122 _diffrn_reflns_av_sigmaI/netI 0.0217 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 27.00 _reflns_number_total 1748 _reflns_number_gt 1481 _reflns_threshold_expression >2sigma(I) #------------------------------------------------------------------------------ _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'Nonius DENZO' _computing_data_reduction 'Nonius DENZO' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0420P)^2^+0.1390P] 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 refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.054(11) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1748 _refine_ls_number_parameters 150 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0453 _refine_ls_R_factor_gt 0.0363 _refine_ls_wR_factor_ref 0.0942 _refine_ls_wR_factor_gt 0.0892 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.061 _refine_ls_shift/su_mean 0.009 #------------------------------------------------------------------------------ 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.94667(10) -0.08809(14) 0.64784(10) 0.0336(3) Uani 1 1 d . . . C2 C 0.84236(11) -0.20966(16) 0.61550(11) 0.0410(3) Uani 1 1 d . . . H2 H 0.7895(13) -0.2168(18) 0.5249(13) 0.051(4) Uiso 1 1 d . . . C3 C 0.81269(12) -0.32110(17) 0.70816(12) 0.0473(3) Uani 1 1 d . . . H3 H 0.7380(14) -0.407(2) 0.6810(14) 0.059(4) Uiso 1 1 d . . . C4 C 0.88773(13) -0.31075(17) 0.83502(12) 0.0483(3) Uani 1 1 d . . . H4 H 0.8691(14) -0.390(2) 0.9001(14) 0.061(4) Uiso 1 1 d . . . C5 C 0.98953(12) -0.18785(17) 0.86930(11) 0.0437(3) Uani 1 1 d . . . H5 H 1.0425(12) -0.1767(19) 0.9619(13) 0.052(4) Uiso 1 1 d . . . C6 C 1.02025(10) -0.07323(15) 0.77777(10) 0.0360(3) Uani 1 1 d . . . C7 C 1.12761(12) 0.06634(17) 0.81944(12) 0.0450(3) Uani 1 1 d . . . H7A H 1.1936(13) 0.0490(19) 0.7684(13) 0.054(4) Uiso 1 1 d . . . H7B H 1.1718(13) 0.0480(19) 0.9131(14) 0.056(4) Uiso 1 1 d . . . C8 C 1.08068(13) 0.26604(18) 0.80151(12) 0.0475(3) Uani 1 1 d . . . H8A H 0.9999(14) 0.278(2) 0.8307(13) 0.056(4) Uiso 1 1 d . . . H8B H 1.1503(14) 0.349(2) 0.8582(14) 0.061(4) Uiso 1 1 d . . . C9 C 1.05273(13) 0.33736(17) 0.66334(12) 0.0456(3) Uani 1 1 d . . . H9A H 1.1348(13) 0.3341(18) 0.6371(12) 0.050(3) Uiso 1 1 d . . . H9B H 1.0263(13) 0.469(2) 0.6619(12) 0.057(4) Uiso 1 1 d . . . C10 C 0.94747(11) 0.23476(16) 0.56132(11) 0.0402(3) Uani 1 1 d . . . H10A H 0.8620(13) 0.2453(18) 0.5851(12) 0.049(3) Uiso 1 1 d . . . H10B H 0.9346(12) 0.2973(18) 0.4763(13) 0.045(3) Uiso 1 1 d . . . C11 C 0.97635(9) 0.03352(14) 0.54716(9) 0.0333(3) Uani 1 1 d . . . #------------------------------------------------------------------------------ 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 C1 0.0339(5) 0.0358(5) 0.0339(5) 0.0052(4) 0.0143(4) 0.0035(4) C2 0.0410(6) 0.0450(6) 0.0399(6) 0.0004(5) 0.0162(5) -0.0038(5) C3 0.0509(7) 0.0432(7) 0.0559(7) -0.0001(5) 0.0285(6) -0.0079(5) C4 0.0626(8) 0.0433(7) 0.0489(7) 0.0116(5) 0.0321(6) 0.0031(6) C5 0.0528(7) 0.0458(7) 0.0350(6) 0.0088(5) 0.0164(5) 0.0086(5) C6 0.0375(6) 0.0366(6) 0.0354(5) 0.0050(4) 0.0125(4) 0.0061(4) C7 0.0419(6) 0.0501(7) 0.0395(6) 0.0048(5) 0.0057(5) -0.0006(5) C8 0.0550(7) 0.0447(7) 0.0441(7) -0.0040(5) 0.0158(6) -0.0061(6) C9 0.0579(7) 0.0348(6) 0.0503(7) 0.0013(5) 0.0250(6) -0.0027(5) C10 0.0437(6) 0.0402(6) 0.0403(6) 0.0103(5) 0.0173(5) 0.0065(5) C11 0.0299(5) 0.0381(6) 0.0312(5) 0.0069(4) 0.0076(4) -0.0007(4) #------------------------------------------------------------------------------ _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 C1 C2 1.3922(15) . ? C1 C6 1.4031(15) . ? C1 C11 1.5005(13) . ? C2 C3 1.3897(16) . ? C3 C4 1.3781(18) . ? C4 C5 1.3796(18) . ? C5 C6 1.3987(15) . ? C6 C7 1.5068(16) . ? C7 C8 1.5332(18) . ? C8 C9 1.5226(17) . ? C9 C10 1.5303(17) . ? C10 C11 1.5143(16) . ? C11 C11 1.347(2) 3_756 ? #------------------------------------------------------------------------------ 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 C2 C1 C6 119.08(9) . . ? C2 C1 C11 120.88(9) . . ? C6 C1 C11 119.96(9) . . ? C3 C2 C1 121.45(11) . . ? C4 C3 C2 119.37(11) . . ? C3 C4 C5 119.92(11) . . ? C4 C5 C6 121.60(11) . . ? C5 C6 C1 118.51(10) . . ? C5 C6 C7 120.29(10) . . ? C1 C6 C7 121.18(9) . . ? C6 C7 C8 113.94(10) . . ? C9 C8 C7 114.46(10) . . ? C8 C9 C10 115.91(10) . . ? C11 C10 C9 114.46(9) . . ? C11 C11 C1 122.05(12) 3_756 . ? C11 C11 C10 123.88(12) 3_756 . ? C1 C11 C10 114.07(9) . . ? #------------------------------------------------------------------------------ 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -2.41(17) . . . . ? C11 C1 C2 C3 -179.05(10) . . . . ? C1 C2 C3 C4 0.26(18) . . . . ? C2 C3 C4 C5 1.31(19) . . . . ? C3 C4 C5 C6 -0.72(18) . . . . ? C4 C5 C6 C1 -1.43(17) . . . . ? C4 C5 C6 C7 176.83(11) . . . . ? C2 C1 C6 C5 2.94(15) . . . . ? C11 C1 C6 C5 179.61(9) . . . . ? C2 C1 C6 C7 -175.30(10) . . . . ? C11 C1 C6 C7 1.37(15) . . . . ? C5 C6 C7 C8 -113.60(12) . . . . ? C1 C6 C7 C8 64.61(14) . . . . ? C6 C7 C8 C9 -79.40(14) . . . . ? C7 C8 C9 C10 60.46(15) . . . . ? C8 C9 C10 C11 -60.54(14) . . . . ? C2 C1 C11 C11 -70.32(16) . . . 3_756 ? C6 C1 C11 C11 113.07(14) . . . 3_756 ? C2 C1 C11 C10 109.26(12) . . . . ? C6 C1 C11 C10 -67.35(12) . . . . ? C9 C10 C11 C11 -99.77(15) . . . 3_756 ? C9 C10 C11 C1 80.65(12) . . . . ? #------------------------------------------------------------------------------ _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.192 _refine_diff_density_min -0.130 _refine_diff_density_rms 0.026 data_structure_4 _database_code_CSD 182508 #------------------------------------------------------------------------------ _audit_creation_method SHELXL-97 _chemical_name_systematic ; trans-1-(1-Benzocyclobutenyliden)benzocyclobutene ; #------------------------------------------------------------------------------ _publ_section_exptl_refinement ? #------------------------------------------------------------------------------ _chemical_name_common 'japoe08' _chemical_melting_point '181-183 deg.' _chemical_formula_moiety ? _chemical_formula_sum 'C16 H12' _chemical_formula_weight 204.26 #------------------------------------------------------------------------------ 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' #------------------------------------------------------------------------------ _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c #------------------------------------------------------------------------------ loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y+1/2, z+1/2' '-x, -y, -z' '-x, y-1/2, -z-1/2' #------------------------------------------------------------------------------ _cell_length_a 12.259(1) _cell_length_b 5.283(1) _cell_length_c 8.856(1) _cell_angle_alpha 90 _cell_angle_beta 101.07(1) _cell_angle_gamma 90 _cell_volume 562.88(13) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1220 _cell_measurement_theta_min 339 _cell_measurement_theta_max 26.98 #------------------------------------------------------------------------------ _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.205 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 216 _exptl_absorpt_coefficient_mu 0.068 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? #------------------------------------------------------------------------------ _exptl_special_details ; 'grown from n-hexane/methanol' ; #------------------------------------------------------------------------------ _diffrn_ambient_temperature 293(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_type 'Nonius KappaCCD' _diffrn_measurement_method Phi/Omega-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2297 _diffrn_reflns_av_R_equivalents 0.0136 _diffrn_reflns_av_sigmaI/netI 0.0228 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.39 _diffrn_reflns_theta_max 26.98 _reflns_number_total 1220 _reflns_number_gt 968 _reflns_threshold_expression >2sigma(I) #------------------------------------------------------------------------------ _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'Nonius DENZO' _computing_data_reduction 'Nonius DENZO' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0680P)^2^+0.0390P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1220 _refine_ls_number_parameters 98 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0541 _refine_ls_R_factor_gt 0.0419 _refine_ls_wR_factor_ref 0.1192 _refine_ls_wR_factor_gt 0.1114 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 #------------------------------------------------------------------------------ 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.16643(9) 0.0357(2) 0.04123(12) 0.0511(3) Uani 1 1 d . . . C2 C 0.23674(11) 0.2012(3) -0.01402(16) 0.0665(4) Uani 1 1 d . . . H2 H 0.2082(12) 0.328(3) -0.0914(17) 0.081(4) Uiso 1 1 d . . . C3 C 0.34954(11) 0.1699(3) 0.04459(19) 0.0741(4) Uani 1 1 d . . . H3 H 0.4013(15) 0.282(3) 0.0070(19) 0.098(5) Uiso 1 1 d . . . C4 C 0.38858(11) -0.0161(3) 0.15132(18) 0.0746(4) Uani 1 1 d . . . H4 H 0.4704(15) -0.033(3) 0.1904(18) 0.093(5) Uiso 1 1 d . . . C5 C 0.31783(10) -0.1821(3) 0.20668(17) 0.0702(4) Uani 1 1 d . . . H5 H 0.3471(14) -0.315(3) 0.286(2) 0.092(5) Uiso 1 1 d . . . C6 C 0.20614(9) -0.1507(2) 0.14836(13) 0.0549(3) Uani 1 1 d . . . C7 C 0.09018(10) -0.2500(3) 0.15439(15) 0.0610(4) Uani 1 1 d . . . H7A H 0.0668(13) -0.229(3) 0.2551(19) 0.086(4) Uiso 1 1 d . . . H7B H 0.0734(12) -0.434(3) 0.1127(17) 0.079(4) Uiso 1 1 d . . . C8 C 0.04970(9) -0.0388(2) 0.03602(12) 0.0507(3) Uani 1 1 d . . . #------------------------------------------------------------------------------ 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 C1 0.0478(6) 0.0569(7) 0.0486(6) -0.0040(5) 0.0094(4) 0.0035(5) C2 0.0618(7) 0.0683(8) 0.0707(8) 0.0078(7) 0.0161(6) -0.0004(6) C3 0.0583(7) 0.0754(9) 0.0913(10) -0.0054(8) 0.0213(7) -0.0114(7) C4 0.0484(7) 0.0802(10) 0.0915(10) -0.0109(8) 0.0042(7) 0.0002(6) C5 0.0538(7) 0.0726(9) 0.0789(9) 0.0024(7) -0.0003(6) 0.0092(6) C6 0.0501(6) 0.0570(7) 0.0561(6) -0.0023(5) 0.0062(5) 0.0045(5) C7 0.0525(6) 0.0674(8) 0.0624(7) 0.0110(6) 0.0091(5) 0.0038(6) C8 0.0478(5) 0.0594(7) 0.0456(6) -0.0017(5) 0.0106(4) 0.0045(5) #------------------------------------------------------------------------------ _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 C1 C2 1.3816(18) . ? C1 C6 1.3890(16) . ? C1 C8 1.4763(16) . ? C2 C3 1.3904(19) . ? C3 C4 1.384(2) . ? C4 C5 1.387(2) . ? C5 C6 1.3775(16) . ? C6 C7 1.5257(16) . ? C7 C8 1.5462(16) . ? C8 C8 1.327(2) 3 ? #------------------------------------------------------------------------------ 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 C2 C1 C6 122.00(11) . . ? C2 C1 C8 145.53(11) . . ? C6 C1 C8 92.47(9) . . ? C1 C2 C3 115.85(13) . . ? C4 C3 C2 121.88(13) . . ? C5 C4 C3 122.18(13) . . ? C6 C5 C4 115.81(13) . . ? C5 C6 C1 122.29(12) . . ? C5 C6 C7 144.22(12) . . ? C1 C6 C7 93.49(9) . . ? C6 C7 C8 84.73(9) . . ? C8 C8 C1 136.71(14) 3 . ? C8 C8 C7 133.97(14) 3 . ? C1 C8 C7 89.31(8) . . ? #------------------------------------------------------------------------------ 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.18(19) . . . . ? C8 C1 C2 C3 178.85(15) . . . . ? C1 C2 C3 C4 0.2(2) . . . . ? C2 C3 C4 C5 -0.2(2) . . . . ? C3 C4 C5 C6 0.2(2) . . . . ? C4 C5 C6 C1 -0.22(19) . . . . ? C4 C5 C6 C7 -179.53(16) . . . . ? C2 C1 C6 C5 0.21(18) . . . . ? C8 C1 C6 C5 -179.24(12) . . . . ? C2 C1 C6 C7 179.81(12) . . . . ? C8 C1 C6 C7 0.36(9) . . . . ? C5 C6 C7 C8 179.07(18) . . . . ? C1 C6 C7 C8 -0.34(8) . . . . ? C2 C1 C8 C8 -0.2(3) . . . 3 ? C6 C1 C8 C8 178.93(18) . . . 3 ? C2 C1 C8 C7 -179.53(18) . . . . ? C6 C1 C8 C7 -0.35(9) . . . . ? C6 C7 C8 C8 -178.99(18) . . . 3 ? C6 C7 C8 C1 0.32(8) . . . . ? #------------------------------------------------------------------------------ _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.98 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.137 _refine_diff_density_min -0.105 _refine_diff_density_rms 0.026 data_structure_10 _database_code_CSD 182509 #------------------------------------------------------------------------------ _audit_creation_method SHELXL-97 _chemical_name_systematic ; trans-1-(6-Methoxy-1-tetralinylidene)-6-methoxytetralane ; #------------------------------------------------------------------------------ _publ_section_exptl_refinement ? #------------------------------------------------------------------------------ _chemical_name_common 'japoe10' _chemical_melting_point '210-211 deg' _chemical_formula_moiety ? _chemical_formula_sum 'C22 H24 O2' _chemical_formula_weight 320.41 #------------------------------------------------------------------------------ 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 monoclinic _symmetry_space_group_name_H-M C2/c #------------------------------------------------------------------------------ loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' #------------------------------------------------------------------------------ _cell_length_a 26.192(1) _cell_length_b 9.483(1) _cell_length_c 6.913(1) _cell_angle_alpha 90.00 _cell_angle_beta 101.3(1) _cell_angle_gamma 90.00 _cell_volume 1683.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1843 _cell_measurement_theta_min 1.59 _cell_measurement_theta_max 27.00 #------------------------------------------------------------------------------ _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.264 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; 'grown from ethyl acetate' ; #------------------------------------------------------------------------------ _diffrn_ambient_temperature 293(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_type 'Nonius KappaCCD' _diffrn_measurement_method Phi/Omega-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3490 _diffrn_reflns_av_R_equivalents 0.0134 _diffrn_reflns_av_sigmaI/netI 0.0238 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 27.00 _reflns_number_total 1843 _reflns_number_gt 1469 _reflns_threshold_expression >2sigma(I) #------------------------------------------------------------------------------ _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'Nonius DENZO' _computing_data_reduction 'Nonius DENZO' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0600P)^2^+0.5800P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1843 _refine_ls_number_parameters 157 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0548 _refine_ls_R_factor_gt 0.0417 _refine_ls_wR_factor_ref 0.1193 _refine_ls_wR_factor_gt 0.1105 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.033 _refine_ls_shift/su_mean 0.005 #------------------------------------------------------------------------------ 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.33376(5) 0.23087(14) 0.0439(2) 0.0430(3) Uani 1 1 d . . . C2 C 0.38083(5) 0.21506(13) 0.17468(18) 0.0376(3) Uani 1 1 d . . . C3 C 0.42586(4) 0.28138(12) 0.13621(17) 0.0354(3) Uani 1 1 d . . . O4 O 0.28044(4) 0.32272(12) -0.23887(15) 0.0590(3) Uani 1 1 d . . . C5 C 0.41990(5) 0.36822(13) -0.03109(18) 0.0399(3) Uani 1 1 d . . . C6 C 0.47642(5) 0.26924(13) 0.27742(17) 0.0367(3) Uani 1 1 d . . . C7 C 0.32948(5) 0.31389(14) -0.12365(19) 0.0426(3) Uani 1 1 d . . . C8 C 0.37279(5) 0.38540(14) -0.16060(19) 0.0427(3) Uani 1 1 d . . . C9 C 0.43528(6) 0.11176(16) 0.4871(2) 0.0504(4) Uani 1 1 d . . . C10 C 0.38173(6) 0.13136(17) 0.3621(2) 0.0499(4) Uani 1 1 d . . . C11 C 0.46975(5) 0.24135(15) 0.48667(19) 0.0442(3) Uani 1 1 d . . . C12 C 0.27302(7) 0.4163(2) -0.4024(3) 0.0637(5) Uani 1 1 d . . . H1 H 0.4505(6) 0.4241(15) -0.055(2) 0.048(4) Uiso 1 1 d . . . H2 H 0.5047(6) 0.2247(15) 0.579(2) 0.051(4) Uiso 1 1 d . . . H3 H 0.4522(6) 0.3290(17) 0.540(2) 0.060(4) Uiso 1 1 d . . . H4 H 0.3023(6) 0.1845(17) 0.068(2) 0.058(4) Uiso 1 1 d . . . H5 H 0.3602(7) 0.1867(17) 0.441(2) 0.065(5) Uiso 1 1 d . . . H6 H 0.3701(5) 0.4474(16) -0.271(2) 0.052(4) Uiso 1 1 d . . . H7 H 0.4333(6) 0.0877(18) 0.625(3) 0.064(5) Uiso 1 1 d . . . H8 H 0.2942(8) 0.392(2) -0.501(3) 0.085(6) Uiso 1 1 d . . . H9 H 0.2810(7) 0.515(2) -0.356(3) 0.085(6) Uiso 1 1 d . . . H10 H 0.4544(6) 0.0274(18) 0.434(2) 0.068(5) Uiso 1 1 d . . . H11 H 0.3638(7) 0.040(2) 0.332(3) 0.077(5) Uiso 1 1 d . . . H12 H 0.2358(8) 0.406(2) -0.460(3) 0.080(5) Uiso 1 1 d . . . #------------------------------------------------------------------------------ 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 C1 0.0372(6) 0.0445(7) 0.0478(7) 0.0038(6) 0.0095(5) -0.0047(5) C2 0.0385(6) 0.0366(6) 0.0392(6) 0.0016(5) 0.0113(5) 0.0007(5) C3 0.0354(6) 0.0379(6) 0.0340(6) -0.0005(5) 0.0097(5) 0.0009(5) O4 0.0417(6) 0.0743(7) 0.0552(6) 0.0160(5) -0.0047(4) -0.0089(5) C5 0.0390(7) 0.0432(7) 0.0388(6) 0.0038(5) 0.0105(5) -0.0028(5) C6 0.0381(6) 0.0403(6) 0.0323(6) 0.0010(5) 0.0085(5) -0.0001(5) C7 0.0377(7) 0.0465(7) 0.0415(7) 0.0010(5) 0.0027(5) -0.0008(5) C8 0.0443(7) 0.0465(7) 0.0373(6) 0.0069(5) 0.0079(5) 0.0002(6) C9 0.0536(8) 0.0562(9) 0.0415(7) 0.0130(6) 0.0094(6) -0.0032(7) C10 0.0461(8) 0.0557(9) 0.0499(8) 0.0150(6) 0.0146(6) -0.0035(7) C11 0.0443(7) 0.0565(8) 0.0333(6) 0.0018(6) 0.0110(5) -0.0004(6) C12 0.0541(9) 0.0749(12) 0.0549(9) 0.0148(8) -0.0074(8) -0.0024(8) #------------------------------------------------------------------------------ _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 C1 C2 1.387(14) . ? C1 C7 1.387(2) . ? C2 C3 1.407(4) . ? C2 C10 1.5160(18) . ? C3 C5 1.403(3) . ? C3 C6 1.488(15) . ? O4 C7 1.375(13) . ? O4 C12 1.420(3) . ? C5 C8 1.385(14) . ? C6 C6 1.361(6) 2_655 ? C6 C11 1.514(3) . ? C7 C8 1.387(4) . ? C9 C10 1.508(14) . ? C9 C11 1.525(2) . ? #------------------------------------------------------------------------------ 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 C2 C1 C7 121.5(5) . . ? C1 C2 C3 120.0(2) . . ? C1 C2 C10 118.5(6) . . ? C3 C2 C10 121.5(7) . . ? C2 C3 C5 117.1(7) . . ? C2 C3 C6 120.8(2) . . ? C5 C3 C6 121.8(5) . . ? C7 O4 C12 117.8(6) . . ? C8 C5 C3 122.9(5) . . ? C6 C6 C3 123.8(2) 2_655 . ? C6 C6 C11 123.2(8) 2_655 . ? C3 C6 C11 112.7(6) . . ? O4 C7 C8 124.63(15) . . ? O4 C7 C1 115.6(6) . . ? C8 C7 C1 119.7(7) . . ? C5 C8 C7 118.7(2) . . ? C10 C9 C11 112.59(18) . . ? C9 C10 C2 114.3(6) . . ? C6 C11 C9 108.8(6) . . ? #------------------------------------------------------------------------------ _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.149 _refine_diff_density_min -0.144 _refine_diff_density_rms 0.033