Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2001 data_General _audit_creation_date 'Fri May 11 11:22:41 2001' _audit_creation_method 'by teXsan' _audit_update_record ; 2001-05-11 text and data added by Kiyohiko Nakajima ; #--------------------------------------------------------------------------- # PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_coeditor_code ? #--------------------------------------------------------------------------- # SUBMISSION DETAILS _publ_contact_author_name 'Tamotsu Takahashi' _publ_contact_author_address ; Catalysis Research Center and Graduate School of Pharmaceutical Sciences, Hokkaido University, and CREST, Science and Technology Corporation (JST), Sapporo 060-0811, Japan ; _publ_contact_author_email 'tamotsu@cat.hokudai.ac.jp' _publ_contact_author_fax '+81 11 706 3274' _publ_contact_author_phone '+81 11 706 2911' loop_ _publ_author_name 'Duan, Zheng' 'Nakajima, Kiyohiko' 'Takahashi, Tamotsu' _publ_requested_journal 'J. Chem. Soc., Chem. Commun.' _journal_coden_Cambridge 182 #--------------------------------------------------------------------------- data_D112 _database_code_CSD 165561 #--------------------------------------------------------------------------- # CHEMICAL DATA _chemical_formula_sum 'C23 H18 ' _chemical_formula_moiety 'C23 H18 ' _chemical_formula_weight 294.40 #--------------------------------------------------------------------------- # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,y,1/2-z -x,-y,-z x,-y,1/2+z 1/2+x,1/2+y,z 1/2-x,1/2+y,1/2-z 1/2-x,1/2-y,-z 1/2+x,1/2-y,1/2+z _cell_length_a 21.312(1) _cell_length_b 10.6981(6) _cell_length_c 16.2781(8) _cell_angle_alpha 90 _cell_angle_beta 117.713(4) _cell_angle_gamma 90 _cell_volume 3285.7(3) _cell_formula_units_Z 8 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 23.0 _cell_measurement_theta_max 42.3 _cell_measurement_temperature 298 #--------------------------------------------------------------------------- _exptl_crystal_description 'prismatic' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_min 0.600 _exptl_crystal_density_diffrn 1.190 _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 0.507 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.903 _exptl_absorpt_correction_T_max 0.999 #--------------------------------------------------------------------------- # EXPERIMENTAL DATA _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_measurement_device_type 'Enraf-Nonius CAD4' _diffrn_reflns_number 3642 _diffrn_reflns_av_R_equivalents 0.018 _diffrn_reflns_theta_max 74.24 _diffrn_measured_fraction_theta_max 1.0000 _diffrn_reflns_theta_full 74.24 _diffrn_measured_fraction_theta_full 1.0000 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 20 #--------------------------------------------------------------------------- # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > 2.0 sigma(F^2^). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 3355 _reflns_number_gt 2737 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.0440 _refine_ls_wR_factor_ref 0.0704 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 2737 _refine_ls_number_parameters 281 _refine_ls_goodness_of_fit_ref 1.843 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00090|Fo|^2^]' _refine_ls_shift/su_max 0.0009 _refine_diff_density_max 0.19 _refine_diff_density_min -0.19 _refine_ls_extinction_method 'Zachariasen(1967) type 2 Gaussian isotropic' _refine_ls_extinction_coef 0.038(4) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.018 0.009 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'H' 'H' 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; #--------------------------------------------------------------------------- # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 C(1) C 0.36422(7) 0.2401(1) 0.64145(9) 0.0491(3) Uani 1.00 d . . . C(2) C 0.39850(7) 0.3139(1) 0.60484(9) 0.0523(3) Uani 1.00 d . . . C(3) C 0.41070(8) 0.4441(1) 0.6279(1) 0.0606(4) Uani 1.00 d . . . C(4) C 0.38838(9) 0.4928(1) 0.6876(1) 0.0674(4) Uani 1.00 d . . . C(5) C 0.35363(8) 0.4210(1) 0.7264(1) 0.0618(4) Uani 1.00 d . . . C(6) C 0.3314(1) 0.4723(2) 0.7893(1) 0.0802(6) Uani 1.00 d . . . C(7) C 0.2983(1) 0.4011(2) 0.8263(1) 0.0864(6) Uani 1.00 d . . . C(8) C 0.2853(1) 0.2750(2) 0.8033(1) 0.0773(6) Uani 1.00 d . . . C(9) C 0.30632(8) 0.2208(2) 0.7436(1) 0.0622(4) Uani 1.00 d . . . C(10) C 0.34091(7) 0.2920(1) 0.70328(9) 0.0537(3) Uani 1.00 d . . . C(11) C 0.35320(7) 0.1038(1) 0.61847(9) 0.0482(3) Uani 1.00 d . . . C(12) C 0.39827(8) 0.0155(1) 0.6798(1) 0.0595(4) Uani 1.00 d . . . C(13) C 0.39031(10) -0.1102(1) 0.6570(1) 0.0673(5) Uani 1.00 d . . . C(14) C 0.33665(10) -0.1495(1) 0.5732(1) 0.0700(5) Uani 1.00 d . . . C(15) C 0.29047(10) -0.0631(2) 0.5130(1) 0.0707(5) Uani 1.00 d . . . C(16) C 0.29808(8) 0.0625(1) 0.5352(1) 0.0613(4) Uani 1.00 d . . . C(17) C 0.42460(8) 0.2587(1) 0.54201(10) 0.0533(3) Uani 1.00 d . . . C(18) C 0.49568(9) 0.2274(2) 0.5762(1) 0.0677(4) Uani 1.00 d . . . C(19) C 0.5198(1) 0.1739(2) 0.5189(1) 0.0796(6) Uani 1.00 d . . . C(20) C 0.4739(1) 0.1510(2) 0.4271(1) 0.0808(6) Uani 1.00 d . . . C(21) C 0.4036(1) 0.1819(2) 0.3924(1) 0.0805(6) Uani 1.00 d . . . C(22) C 0.37905(9) 0.2359(2) 0.4491(1) 0.0686(5) Uani 1.00 d . . . C(23) C 0.4473(1) 0.5246(2) 0.5873(2) 0.0809(6) Uani 1.00 d . . . H(1) H 0.3964(8) 0.583(2) 0.707(1) 0.069(5) Uiso 1.00 calc . . . H(2) H 0.342(1) 0.561(2) 0.805(1) 0.085(5) Uiso 1.00 calc . . . H(3) H 0.280(1) 0.438(2) 0.869(2) 0.113(7) Uiso 1.00 calc . . . H(4) H 0.264(1) 0.223(2) 0.829(2) 0.100(7) Uiso 1.00 calc . . . H(5) H 0.3001(9) 0.130(2) 0.730(1) 0.075(5) Uiso 1.00 calc . . . H(6) H 0.4362(10) 0.041(2) 0.743(1) 0.078(5) Uiso 1.00 calc . . . H(7) H 0.424(1) -0.167(2) 0.703(1) 0.082(5) Uiso 1.00 calc . . . H(8) H 0.331(1) -0.240(2) 0.557(1) 0.089(6) Uiso 1.00 calc . . . H(9) H 0.251(1) -0.093(2) 0.449(1) 0.088(5) Uiso 1.00 calc . . . H(10) H 0.2657(9) 0.130(2) 0.491(1) 0.074(5) Uiso 1.00 calc . . . H(11) H 0.531(1) 0.243(2) 0.649(1) 0.102(7) Uiso 1.00 calc . . . H(12) H 0.572(1) 0.152(2) 0.549(2) 0.109(7) Uiso 1.00 calc . . . H(13) H 0.497(1) 0.115(2) 0.388(2) 0.107(7) Uiso 1.00 calc . . . H(14) H 0.367(1) 0.167(2) 0.328(2) 0.124(8) Uiso 1.00 calc . . . H(15) H 0.3285(10) 0.258(2) 0.424(1) 0.073(5) Uiso 1.00 calc . . . H(16) H 0.447(1) 0.614(3) 0.603(2) 0.114(7) Uiso 1.00 calc . . . H(17) H 0.495(2) 0.491(3) 0.606(2) 0.136(10) Uiso 1.00 calc . . . H(18) H 0.421(1) 0.528(3) 0.520(2) 0.124(8) Uiso 1.00 calc . . . 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 C(1) 0.0531(7) 0.0420(6) 0.0457(6) 0.0013(5) 0.0175(5) 0.0009(5) C(2) 0.0563(7) 0.0438(7) 0.0505(6) 0.0005(5) 0.0195(5) 0.0034(5) C(3) 0.0675(8) 0.0437(7) 0.0617(8) -0.0018(6) 0.0226(7) 0.0043(6) C(4) 0.081(1) 0.0413(7) 0.0684(9) 0.0000(7) 0.0251(8) -0.0050(6) C(5) 0.0700(9) 0.0499(7) 0.0564(8) 0.0078(6) 0.0216(7) -0.0045(6) C(6) 0.099(1) 0.064(1) 0.077(1) 0.0125(9) 0.0409(10) -0.0140(8) C(7) 0.102(1) 0.091(1) 0.074(1) 0.021(1) 0.048(1) -0.0080(9) C(8) 0.084(1) 0.087(1) 0.070(1) 0.0084(9) 0.0439(9) 0.0014(9) C(9) 0.0673(9) 0.0622(9) 0.0598(8) 0.0023(7) 0.0317(7) -0.0002(6) C(10) 0.0566(7) 0.0500(7) 0.0480(7) 0.0045(6) 0.0188(6) -0.0013(5) C(11) 0.0545(7) 0.0425(6) 0.0507(6) -0.0016(5) 0.0269(5) 0.0007(5) C(12) 0.0633(8) 0.0497(8) 0.0593(8) 0.0029(6) 0.0231(7) 0.0044(6) C(13) 0.0763(10) 0.0464(8) 0.082(1) 0.0065(7) 0.0392(9) 0.0090(7) C(14) 0.090(1) 0.0430(7) 0.088(1) -0.0080(7) 0.0511(10) -0.0097(7) C(15) 0.080(1) 0.0580(9) 0.0658(9) -0.0129(7) 0.0271(8) -0.0119(7) C(16) 0.0664(8) 0.0517(8) 0.0554(7) -0.0020(6) 0.0195(7) -0.0021(6) C(17) 0.0602(7) 0.0449(6) 0.0548(7) -0.0022(5) 0.0267(6) 0.0061(5) C(18) 0.0635(9) 0.0649(9) 0.0694(9) 0.0002(7) 0.0265(8) 0.0037(7) C(19) 0.072(1) 0.077(1) 0.098(1) 0.0068(9) 0.046(1) 0.0043(9) C(20) 0.098(1) 0.076(1) 0.090(1) -0.0012(10) 0.062(1) -0.0030(9) C(21) 0.088(1) 0.095(1) 0.0638(10) -0.006(1) 0.0395(9) -0.0074(9) C(22) 0.0657(9) 0.082(1) 0.0567(8) 0.0002(8) 0.0273(7) 0.0030(7) C(23) 0.099(1) 0.0504(9) 0.092(1) -0.0114(9) 0.044(1) 0.0092(9) #--------------------------------------------------------------------------- #-- _computing_data_collection 'CAD4 (Enraf-Nonius, 1989)' _computing_cell_refinement 'CAD4 (Enraf-Nonius, 1989)' _computing_data_reduction 'teXsan Ver. 1.10' _computing_structure_solution SIR92 _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.10' _computing_molecular_graphics ? #--------------------------------------------------------------------------- _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 C(1) C(2) 1.385(2) . . no C(1) C(10) 1.426(2) . . no C(1) C(11) 1.497(2) . . no C(2) C(3) 1.435(2) . . no C(2) C(17) 1.495(2) . . no C(3) C(4) 1.368(2) . . no C(3) C(23) 1.505(2) . . no C(4) C(5) 1.405(2) . . no C(5) C(6) 1.422(2) . . no C(5) C(10) 1.423(2) . . no C(6) C(7) 1.355(3) . . no C(7) C(8) 1.393(3) . . no C(8) C(9) 1.372(2) . . no C(9) C(10) 1.416(2) . . no C(11) C(12) 1.385(2) . . no C(11) C(16) 1.390(2) . . no C(12) C(13) 1.384(2) . . no C(13) C(14) 1.376(3) . . no C(14) C(15) 1.374(3) . . no C(15) C(16) 1.382(2) . . no C(17) C(18) 1.390(2) . . no C(17) C(22) 1.387(2) . . no C(18) C(19) 1.382(3) . . no C(19) C(20) 1.376(3) . . no C(20) C(21) 1.373(3) . . no C(21) C(22) 1.381(2) . . 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) C(1) C(10) 120.6(1) . 1_555 1_555 no C(2) C(1) C(11) 120.1(1) . 1_555 1_555 no C(10) C(1) C(11) 119.3(1) . 1_555 1_555 no C(1) C(2) C(3) 120.6(1) . 1_555 1_555 no C(1) C(2) C(17) 120.5(1) . 1_555 1_555 no C(3) C(2) C(17) 118.9(1) . 1_555 1_555 no C(2) C(3) C(4) 118.4(1) . 1_555 1_555 no C(2) C(3) C(23) 120.5(1) . 1_555 1_555 no C(4) C(3) C(23) 121.1(1) . 1_555 1_555 no C(3) C(4) C(5) 122.8(1) . 1_555 1_555 no C(4) C(5) C(6) 122.3(1) . 1_555 1_555 no C(4) C(5) C(10) 119.1(1) . 1_555 1_555 no C(6) C(5) C(10) 118.5(2) . 1_555 1_555 no C(5) C(6) C(7) 121.4(2) . 1_555 1_555 no C(6) C(7) C(8) 120.2(2) . 1_555 1_555 no C(7) C(8) C(9) 120.7(2) . 1_555 1_555 no C(8) C(9) C(10) 120.8(2) . 1_555 1_555 no C(1) C(10) C(5) 118.6(1) . 1_555 1_555 no C(1) C(10) C(9) 123.1(1) . 1_555 1_555 no C(5) C(10) C(9) 118.4(1) . 1_555 1_555 no C(1) C(11) C(12) 120.6(1) . 1_555 1_555 no C(1) C(11) C(16) 121.1(1) . 1_555 1_555 no C(12) C(11) C(16) 118.3(1) . 1_555 1_555 no C(11) C(12) C(13) 120.8(1) . 1_555 1_555 no C(12) C(13) C(14) 120.3(2) . 1_555 1_555 no C(13) C(14) C(15) 119.4(1) . 1_555 1_555 no C(14) C(15) C(16) 120.7(2) . 1_555 1_555 no C(11) C(16) C(15) 120.5(1) . 1_555 1_555 no C(2) C(17) C(18) 120.3(1) . 1_555 1_555 no C(2) C(17) C(22) 121.4(1) . 1_555 1_555 no C(18) C(17) C(22) 118.3(1) . 1_555 1_555 no C(17) C(18) C(19) 120.5(2) . 1_555 1_555 no C(18) C(19) C(20) 120.4(2) . 1_555 1_555 no C(19) C(20) C(21) 119.6(2) . 1_555 1_555 no C(20) C(21) C(22) 120.4(2) . 1_555 1_555 no C(17) C(22) C(21) 120.8(2) . 1_555 1_555 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C(1) C(2) C(3) C(4) 0.7(2) 1_555 1_555 1_555 1_555 no C(1) C(2) C(3) C(23) -179.3(1) 1_555 1_555 1_555 1_555 no C(1) C(2) C(17) C(18) -100.0(2) 1_555 1_555 1_555 1_555 no C(1) C(2) C(17) C(22) 79.2(2) 1_555 1_555 1_555 1_555 no C(1) C(10) C(5) C(4) 0.2(2) 1_555 1_555 1_555 1_555 no C(1) C(10) C(5) C(6) -179.0(1) 1_555 1_555 1_555 1_555 no C(1) C(10) C(9) C(8) 179.6(1) 1_555 1_555 1_555 1_555 no C(1) C(11) C(12) C(13) -176.9(1) 1_555 1_555 1_555 1_555 no C(1) C(11) C(16) C(15) 177.0(1) 1_555 1_555 1_555 1_555 no C(2) C(1) C(10) C(5) 0.0(2) 1_555 1_555 1_555 1_555 no C(2) C(1) C(10) C(9) -179.3(1) 1_555 1_555 1_555 1_555 no C(2) C(1) C(11) C(12) 99.0(2) 1_555 1_555 1_555 1_555 no C(2) C(1) C(11) C(16) -80.6(2) 1_555 1_555 1_555 1_555 no C(2) C(3) C(4) C(5) -0.6(2) 1_555 1_555 1_555 1_555 no C(2) C(17) C(18) C(19) 178.7(1) 1_555 1_555 1_555 1_555 no C(2) C(17) C(22) C(21) -178.4(2) 1_555 1_555 1_555 1_555 no C(3) C(2) C(1) C(10) -0.5(2) 1_555 1_555 1_555 1_555 no C(3) C(2) C(1) C(11) -178.7(1) 1_555 1_555 1_555 1_555 no C(3) C(2) C(17) C(18) 78.9(2) 1_555 1_555 1_555 1_555 no C(3) C(2) C(17) C(22) -101.9(2) 1_555 1_555 1_555 1_555 no C(3) C(4) C(5) C(6) 179.2(1) 1_555 1_555 1_555 1_555 no C(3) C(4) C(5) C(10) 0.1(2) 1_555 1_555 1_555 1_555 no C(4) C(3) C(2) C(17) -178.1(1) 1_555 1_555 1_555 1_555 no C(4) C(5) C(6) C(7) -179.7(2) 1_555 1_555 1_555 1_555 no C(4) C(5) C(10) C(9) 179.5(1) 1_555 1_555 1_555 1_555 no C(5) C(4) C(3) C(23) 179.5(2) 1_555 1_555 1_555 1_555 no C(5) C(6) C(7) C(8) 0.2(3) 1_555 1_555 1_555 1_555 no C(5) C(10) C(1) C(11) 178.3(1) 1_555 1_555 1_555 1_555 no C(5) C(10) C(9) C(8) 0.2(2) 1_555 1_555 1_555 1_555 no C(6) C(5) C(10) C(9) 0.4(2) 1_555 1_555 1_555 1_555 no C(6) C(7) C(8) C(9) 0.5(3) 1_555 1_555 1_555 1_555 no C(7) C(6) C(5) C(10) -0.6(3) 1_555 1_555 1_555 1_555 no C(7) C(8) C(9) C(10) -0.7(3) 1_555 1_555 1_555 1_555 no C(9) C(10) C(1) C(11) -1.1(2) 1_555 1_555 1_555 1_555 no C(10) C(1) C(2) C(17) 178.4(1) 1_555 1_555 1_555 1_555 no C(10) C(1) C(11) C(12) -79.2(2) 1_555 1_555 1_555 1_555 no C(10) C(1) C(11) C(16) 101.2(2) 1_555 1_555 1_555 1_555 no C(11) C(1) C(2) C(17) 0.2(2) 1_555 1_555 1_555 1_555 no C(11) C(12) C(13) C(14) -0.9(3) 1_555 1_555 1_555 1_555 no C(11) C(16) C(15) C(14) 0.8(3) 1_555 1_555 1_555 1_555 no C(12) C(11) C(16) C(15) -2.5(2) 1_555 1_555 1_555 1_555 no C(12) C(13) C(14) C(15) -0.9(3) 1_555 1_555 1_555 1_555 no C(13) C(12) C(11) C(16) 2.6(2) 1_555 1_555 1_555 1_555 no C(13) C(14) C(15) C(16) 0.9(3) 1_555 1_555 1_555 1_555 no C(17) C(2) C(3) C(23) 1.8(2) 1_555 1_555 1_555 1_555 no C(17) C(18) C(19) C(20) 0.1(3) 1_555 1_555 1_555 1_555 no C(17) C(22) C(21) C(20) -0.7(3) 1_555 1_555 1_555 1_555 no C(18) C(17) C(22) C(21) 0.9(2) 1_555 1_555 1_555 1_555 no C(18) C(19) C(20) C(21) 0.2(3) 1_555 1_555 1_555 1_555 no C(19) C(18) C(17) C(22) -0.6(2) 1_555 1_555 1_555 1_555 no C(19) C(20) C(21) C(22) 0.1(3) 1_555 1_555 1_555 1_555 no #--------------------------------------------------------------------------- #-- #===END