# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_coden_Cambridge 182 _publ_contact_author_name 'Ben Zhong Tang' _publ_contact_author_address ; Department of Chemistry Hong Kong University of Science & Technology Clear Water Bay, Kowloon HONG KONG ; _publ_contact_author_email TANGBENZ@UST.HK _publ_requested_journal Chem.Commun. _publ_section_title ; Novel molecule isolated from rubrene with aggregation-induced characteristics: 1,2-diphenyl-3,4-bis(diphenylmethylene)-1-cyclobutenenhancement ; loop_ _publ_author_name 'Ben Zhong Tang' 'Yongqiang Dong' 'Jacky W. Y. Lam' 'Anjun Qin' 'Jiaxin Sun' 'Jianzhao Liu' 'Zhen Li' 'Jingzhi Sun' 'Herman H-Y. Sung' 'Ian D. Williams' 'Hoi Sing Kwok' data_1 _database_code_depnum_ccdc_archive 'CCDC 642388' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C46 H38 O' _chemical_formula_weight 606.76 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 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 19.641(10) _cell_length_b 16.858(9) _cell_length_c 9.925(5) _cell_angle_alpha 90.00 _cell_angle_beta 92.159(11) _cell_angle_gamma 90.00 _cell_volume 3284(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1523 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 25.75 _exptl_crystal_description bar _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.227 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1288 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.82 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6834 _diffrn_reflns_av_R_equivalents 0.0358 _diffrn_reflns_av_sigmaI/netI 0.0573 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2943 _reflns_number_gt 2308 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0673P)^2^+2.0000P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2943 _refine_ls_number_parameters 210 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0750 _refine_ls_R_factor_gt 0.0560 _refine_ls_wR_factor_ref 0.1393 _refine_ls_wR_factor_gt 0.1302 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.028 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.46559(10) 0.66944(11) 0.25722(18) 0.0155(4) Uani 1 1 d . . . C2 C 0.46169(10) 0.58067(11) 0.25810(18) 0.0150(4) Uani 1 1 d . . . C3 C 0.40934(9) 0.52952(11) 0.26863(18) 0.0153(4) Uani 1 1 d . . . C11 C 0.41620(9) 0.73439(11) 0.27194(19) 0.0161(4) Uani 1 1 d . . . C12 C 0.36954(10) 0.73362(11) 0.3745(2) 0.0193(5) Uani 1 1 d . . . H12 H 0.3691 0.6905 0.4360 0.023 Uiso 1 1 calc R . . C13 C 0.32378(11) 0.79575(12) 0.3868(2) 0.0252(5) Uani 1 1 d . . . H13A H 0.2927 0.7952 0.4579 0.030 Uiso 1 1 calc R . . C14 C 0.32295(11) 0.85898(13) 0.2960(2) 0.0281(5) Uani 1 1 d . . . H14A H 0.2911 0.9009 0.3041 0.034 Uiso 1 1 calc R . . C15 C 0.36898(11) 0.85996(12) 0.1942(2) 0.0265(5) Uani 1 1 d . . . H15A H 0.3685 0.9025 0.1314 0.032 Uiso 1 1 calc R . . C16 C 0.41594(10) 0.79915(12) 0.1832(2) 0.0207(5) Uani 1 1 d . . . H16A H 0.4484 0.8014 0.1146 0.025 Uiso 1 1 calc R . . C21 C 0.33774(10) 0.55981(11) 0.2550(2) 0.0172(4) Uani 1 1 d . . . C22 C 0.31617(10) 0.60608(12) 0.1436(2) 0.0223(5) Uani 1 1 d . . . H22A H 0.3477 0.6203 0.0774 0.027 Uiso 1 1 calc R . . C23 C 0.24911(11) 0.63101(12) 0.1303(2) 0.0312(6) Uani 1 1 d . . . H23A H 0.2346 0.6621 0.0547 0.037 Uiso 1 1 calc R . . C24 C 0.20331(11) 0.61071(13) 0.2265(3) 0.0353(6) Uani 1 1 d . . . H24A H 0.1573 0.6277 0.2167 0.042 Uiso 1 1 calc R . . C25 C 0.22408(11) 0.56574(12) 0.3372(3) 0.0301(5) Uani 1 1 d . . . H25A H 0.1925 0.5527 0.4039 0.036 Uiso 1 1 calc R . . C26 C 0.29056(10) 0.53986(12) 0.3508(2) 0.0228(5) Uani 1 1 d . . . H26A H 0.3043 0.5082 0.4262 0.027 Uiso 1 1 calc R . . C31 C 0.41512(9) 0.44281(11) 0.29403(18) 0.0155(4) Uani 1 1 d . . . C32 C 0.36909(10) 0.39016(12) 0.2298(2) 0.0191(4) Uani 1 1 d . . . H32A H 0.3349 0.4105 0.1690 0.023 Uiso 1 1 calc R . . C33 C 0.37243(10) 0.30893(12) 0.2530(2) 0.0227(5) Uani 1 1 d . . . H33A H 0.3406 0.2744 0.2088 0.027 Uiso 1 1 calc R . . C34 C 0.42258(11) 0.27839(12) 0.3414(2) 0.0219(5) Uani 1 1 d . . . H34A H 0.4255 0.2229 0.3570 0.026 Uiso 1 1 calc R . . C35 C 0.46819(10) 0.32938(11) 0.40644(19) 0.0190(4) Uani 1 1 d . . . H35A H 0.5024 0.3087 0.4669 0.023 Uiso 1 1 calc R . . C36 C 0.46435(10) 0.41095(11) 0.38400(19) 0.0167(4) Uani 1 1 d . . . H36A H 0.4956 0.4453 0.4304 0.020 Uiso 1 1 calc R . . O1S O 0.53641(18) 0.9231(2) 0.5774(4) 0.0420(9) Uiso 0.50 1 d PD . . C1S C 0.4658(3) 0.9224(5) 0.5413(7) 0.0534(18) Uiso 0.50 1 d PD . . C2S C 0.4577(3) 0.9876(4) 0.4283(6) 0.0396(16) Uiso 0.50 1 d PD . . C3S C 0.5267(3) 1.0455(4) 0.4640(6) 0.0408(15) Uiso 0.50 1 d PD . . C4S C 0.5632(4) 0.9973(4) 0.5811(7) 0.053(2) Uiso 0.50 1 d PD . . 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 0.0177(9) 0.0156(10) 0.0130(9) 0.0004(7) -0.0007(7) 0.0008(8) C2 0.0173(10) 0.0159(10) 0.0117(9) -0.0006(7) -0.0005(7) 0.0022(8) C3 0.0157(10) 0.0167(10) 0.0133(9) -0.0012(7) -0.0011(7) 0.0019(8) C11 0.0137(10) 0.0151(10) 0.0193(10) -0.0032(7) -0.0017(8) -0.0014(7) C12 0.0171(11) 0.0168(10) 0.0240(11) -0.0010(8) 0.0016(8) -0.0031(8) C13 0.0171(11) 0.0236(11) 0.0352(13) -0.0068(9) 0.0056(9) -0.0032(9) C14 0.0182(11) 0.0218(11) 0.0443(14) -0.0066(9) -0.0014(10) 0.0045(9) C15 0.0292(12) 0.0199(11) 0.0301(12) 0.0026(9) -0.0026(9) 0.0040(9) C16 0.0200(11) 0.0209(11) 0.0211(11) -0.0004(8) 0.0002(8) 0.0006(8) C21 0.0147(10) 0.0125(9) 0.0242(10) -0.0048(8) -0.0010(8) -0.0004(8) C22 0.0220(11) 0.0183(10) 0.0261(11) -0.0031(8) -0.0064(9) -0.0003(8) C23 0.0283(13) 0.0189(11) 0.0450(14) -0.0041(10) -0.0156(11) 0.0036(9) C24 0.0144(11) 0.0225(12) 0.0684(18) -0.0134(11) -0.0059(11) 0.0040(9) C25 0.0177(11) 0.0208(11) 0.0525(15) -0.0099(10) 0.0106(10) -0.0037(9) C26 0.0201(11) 0.0169(10) 0.0316(12) -0.0035(8) 0.0042(9) -0.0011(8) C31 0.0141(10) 0.0186(10) 0.0143(9) 0.0008(7) 0.0055(7) 0.0004(8) C32 0.0147(10) 0.0207(10) 0.0218(10) 0.0010(8) -0.0011(8) 0.0000(8) C33 0.0217(11) 0.0195(10) 0.0267(11) -0.0021(8) -0.0030(9) -0.0054(9) C34 0.0288(12) 0.0152(10) 0.0219(11) 0.0036(8) 0.0014(9) -0.0003(9) C35 0.0201(11) 0.0206(10) 0.0161(10) 0.0018(8) -0.0009(8) 0.0015(8) C36 0.0150(10) 0.0195(10) 0.0157(10) -0.0026(7) 0.0020(7) -0.0026(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 C1 1.365(4) 2_655 ? C1 C11 1.474(3) . ? C1 C2 1.498(3) . ? C2 C3 1.349(3) . ? C2 C2 1.519(4) 2_655 ? C3 C31 1.487(3) . ? C3 C21 1.497(3) . ? C11 C12 1.395(3) . ? C11 C16 1.403(3) . ? C12 C13 1.389(3) . ? C13 C14 1.396(3) . ? C14 C15 1.381(3) . ? C15 C16 1.386(3) . ? C21 C26 1.394(3) . ? C21 C22 1.405(3) . ? C22 C23 1.384(3) . ? C23 C24 1.380(4) . ? C24 C25 1.384(4) . ? C25 C26 1.378(3) . ? C31 C36 1.399(3) . ? C31 C32 1.403(3) . ? C32 C33 1.390(3) . ? C33 C34 1.393(3) . ? C34 C35 1.384(3) . ? C35 C36 1.395(3) . ? O1S C4S 1.358(8) . ? O1S C1S 1.420(7) . ? C1S C2S 1.574(9) . ? C2S C3S 1.234(8) 5_676 ? C2S C3S 1.697(9) . ? C3S C2S 1.234(8) 5_676 ? C3S C4S 1.568(9) . ? 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 C1 C1 C11 131.97(11) 2_655 . ? C1 C1 C2 92.96(10) 2_655 . ? C11 C1 C2 135.03(18) . . ? C3 C2 C1 132.69(18) . . ? C3 C2 C2 140.27(11) . 2_655 ? C1 C2 C2 87.04(10) . 2_655 ? C2 C3 C31 126.01(17) . . ? C2 C3 C21 119.41(17) . . ? C31 C3 C21 114.58(16) . . ? C12 C11 C16 118.59(18) . . ? C12 C11 C1 121.22(17) . . ? C16 C11 C1 120.18(18) . . ? C13 C12 C11 120.17(19) . . ? C12 C13 C14 120.7(2) . . ? C15 C14 C13 119.3(2) . . ? C14 C15 C16 120.3(2) . . ? C15 C16 C11 120.9(2) . . ? C26 C21 C22 118.83(19) . . ? C26 C21 C3 120.17(18) . . ? C22 C21 C3 120.96(18) . . ? C23 C22 C21 120.1(2) . . ? C24 C23 C22 120.1(2) . . ? C23 C24 C25 120.3(2) . . ? C26 C25 C24 120.1(2) . . ? C25 C26 C21 120.5(2) . . ? C36 C31 C32 117.73(18) . . ? C36 C31 C3 122.17(17) . . ? C32 C31 C3 120.07(17) . . ? C33 C32 C31 121.50(18) . . ? C32 C33 C34 119.77(18) . . ? C35 C34 C33 119.62(18) . . ? C34 C35 C36 120.53(17) . . ? C35 C36 C31 120.83(17) . . ? C4S O1S C1S 112.8(5) . . ? O1S C1S C2S 104.2(5) . . ? C1S C2S C3S 101.2(6) . . ? C4S C3S C2S 101.3(6) . . ? O1S C4S C3S 107.0(5) . . ? _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 0.407 _refine_diff_density_min -0.264 _refine_diff_density_rms 0.047