Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2002 data_010523c _database_code_CSD 190058 _journal_coden_Cambridge 182 loop_ _publ_author_name 'Meng, Jiben' 'Mastuura, Teruo' 'Sugiyama, Teruki' 'Xu, Lili' _publ_contact_author_name 'Prof Jiben Meng' _publ_contact_author_address ; The Department of Chemistry Nankai University The Department of Chemistry Tianjin 300071 CHINA ; _publ_contact_author_email 'MENGJIBEN@EYOU.COM' _publ_requested_journal 'Chemical Communications' _publ_section_title ; Photoinduced ground-state singlet biradical ¨C novel insight into the photochromic compounds of biindenylidenediones ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H24 O4' _chemical_formula_weight 376.43 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 10.398(3) _cell_length_b 12.481(4) _cell_length_c 15.371(4) _cell_angle_alpha 90.00 _cell_angle_beta 105.014(5) _cell_angle_gamma 90.00 _cell_volume 1926.8(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Rhombic _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.298 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9743 _exptl_absorpt_correction_T_max 0.9827 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2 _diffrn_reflns_number 4885 _diffrn_reflns_av_R_equivalents 0.0633 _diffrn_reflns_av_sigmaI/netI 0.0749 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 25.02 _reflns_number_total 1712 _reflns_number_gt 900 _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^)+(0.0521P)^2^+0.0000P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1712 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1117 _refine_ls_R_factor_gt 0.0489 _refine_ls_wR_factor_ref 0.1254 _refine_ls_wR_factor_gt 0.1064 _refine_ls_goodness_of_fit_ref 0.989 _refine_ls_restrained_S_all 0.989 _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 O1 O 0.11730(18) 0.61358(14) 0.37517(11) 0.0517(5) Uani 1 1 d . . . O2 O 0.44290(17) 0.87903(14) 0.46251(12) 0.0523(5) Uani 1 1 d . . . H2B H 0.4550 0.8847 0.5172 0.078 Uiso 1 1 calc R . . C1 C 0.2159(2) 0.74391(19) 0.29872(17) 0.0401(6) Uani 1 1 d . . . C2 C 0.1813(3) 0.7094(2) 0.20922(18) 0.0500(8) Uani 1 1 d . . . H2A H 0.1291 0.6486 0.1922 0.060 Uiso 1 1 calc R . . C3 C 0.2261(3) 0.7671(2) 0.14709(19) 0.0588(8) Uani 1 1 d . . . H3A H 0.2028 0.7462 0.0870 0.071 Uiso 1 1 calc R . . C4 C 0.3058(3) 0.8565(2) 0.1732(2) 0.0588(8) Uani 1 1 d . . . H4A H 0.3384 0.8932 0.1308 0.071 Uiso 1 1 calc R . . C5 C 0.3377(3) 0.8918(2) 0.26165(18) 0.0509(7) Uani 1 1 d . . . H5A H 0.3894 0.9529 0.2785 0.061 Uiso 1 1 calc R . . C6 C 0.2912(2) 0.83480(19) 0.32455(17) 0.0399(7) Uani 1 1 d . . . C7 C 0.3051(3) 0.86210(18) 0.42183(16) 0.0395(7) Uani 1 1 d . . . C8 C 0.2476(2) 0.76250(18) 0.45740(15) 0.0364(6) Uani 1 1 d . . . C9 C 0.1835(3) 0.6949(2) 0.37680(17) 0.0401(7) Uani 1 1 d . . . C10 C 0.2251(3) 0.96425(19) 0.42929(18) 0.0436(7) Uani 1 1 d . . . H10A H 0.2333 0.9784 0.4925 0.052 Uiso 1 1 calc R . . H10B H 0.2652 1.0240 0.4057 0.052 Uiso 1 1 calc R . . C11 C 0.0799(3) 0.9604(2) 0.38119(19) 0.0577(8) Uani 1 1 d . . . H11A H 0.0378 0.9043 0.4078 0.069 Uiso 1 1 calc R . . H11B H 0.0710 0.9415 0.3187 0.069 Uiso 1 1 calc R . . C12 C 0.0071(3) 1.0639(2) 0.3843(2) 0.0749(10) Uani 1 1 d . . . H12A H -0.0849 1.0554 0.3526 0.112 Uiso 1 1 calc R . . H12B H 0.0461 1.1196 0.3565 0.112 Uiso 1 1 calc R . . H12C H 0.0135 1.0826 0.4459 0.112 Uiso 1 1 calc R . . 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 0.0587(12) 0.0446(11) 0.0476(12) -0.0001(9) 0.0062(10) -0.0092(10) O2 0.0406(11) 0.0641(12) 0.0488(12) 0.0017(9) 0.0053(10) -0.0074(9) C1 0.0409(15) 0.0418(15) 0.0379(16) -0.0003(13) 0.0106(13) 0.0070(13) C2 0.0567(18) 0.0435(16) 0.0477(19) -0.0029(14) 0.0097(16) 0.0047(14) C3 0.074(2) 0.061(2) 0.0431(18) 0.0024(16) 0.0183(17) 0.0099(18) C4 0.075(2) 0.0555(19) 0.055(2) 0.0077(15) 0.0325(18) 0.0042(17) C5 0.0604(19) 0.0454(16) 0.0520(19) 0.0031(15) 0.0236(16) 0.0011(15) C6 0.0421(17) 0.0373(15) 0.0429(17) 0.0035(12) 0.0157(14) 0.0051(13) C7 0.0380(15) 0.0395(15) 0.0384(16) 0.0011(12) 0.0050(13) -0.0017(12) C8 0.0355(13) 0.0342(14) 0.0380(14) 0.0012(12) 0.0067(14) 0.0032(12) C9 0.0384(15) 0.0359(15) 0.0435(17) 0.0043(13) 0.0064(14) 0.0058(13) C10 0.0532(18) 0.0370(15) 0.0410(16) 0.0039(12) 0.0128(15) 0.0021(13) C11 0.0534(19) 0.0609(19) 0.0548(19) -0.0034(15) 0.0068(16) 0.0151(16) C12 0.076(2) 0.064(2) 0.090(3) 0.0088(18) 0.031(2) 0.0259(18) _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 C9 1.223(3) . ? O2 C7 1.423(3) . ? O2 H2B 0.8200 . ? C1 C6 1.377(3) . ? C1 C2 1.397(3) . ? C1 C9 1.462(3) . ? C2 C3 1.370(3) . ? C2 H2A 0.9300 . ? C3 C4 1.386(4) . ? C3 H3A 0.9300 . ? C4 C5 1.385(4) . ? C4 H4A 0.9300 . ? C5 C6 1.384(3) . ? C5 H5A 0.9300 . ? C6 C7 1.504(3) . ? C7 C8 1.540(3) . ? C7 C10 1.543(3) . ? C8 C8 1.335(4) 7_566 ? C8 C9 1.504(3) . ? C10 C11 1.501(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.504(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? 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 C7 O2 H2B 109.5 . . ? C6 C1 C2 121.4(2) . . ? C6 C1 C9 110.0(2) . . ? C2 C1 C9 128.6(2) . . ? C3 C2 C1 118.5(3) . . ? C3 C2 H2A 120.8 . . ? C1 C2 H2A 120.8 . . ? C2 C3 C4 120.5(3) . . ? C2 C3 H3A 119.8 . . ? C4 C3 H3A 119.8 . . ? C5 C4 C3 120.9(3) . . ? C5 C4 H4A 119.5 . . ? C3 C4 H4A 119.5 . . ? C6 C5 C4 118.9(3) . . ? C6 C5 H5A 120.5 . . ? C4 C5 H5A 120.5 . . ? C1 C6 C5 119.8(2) . . ? C1 C6 C7 112.0(2) . . ? C5 C6 C7 128.1(2) . . ? O2 C7 C6 107.3(2) . . ? O2 C7 C8 113.78(19) . . ? C6 C7 C8 102.94(19) . . ? O2 C7 C10 110.22(19) . . ? C6 C7 C10 110.3(2) . . ? C8 C7 C10 112.0(2) . . ? C8 C8 C9 125.0(3) 7_566 . ? C8 C8 C7 128.2(3) 7_566 . ? C9 C8 C7 106.9(2) . . ? O1 C9 C1 125.3(2) . . ? O1 C9 C8 127.5(2) . . ? C1 C9 C8 107.1(2) . . ? C11 C10 C7 115.5(2) . . ? C11 C10 H10A 108.4 . . ? C7 C10 H10A 108.4 . . ? C11 C10 H10B 108.4 . . ? C7 C10 H10B 108.4 . . ? H10A C10 H10B 107.5 . . ? C10 C11 C12 114.1(2) . . ? C10 C11 H11A 108.7 . . ? C12 C11 H11A 108.7 . . ? C10 C11 H11B 108.7 . . ? C12 C11 H11B 108.7 . . ? H11A C11 H11B 107.6 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? 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 1.2(4) . . . . ? C9 C1 C2 C3 -178.3(2) . . . . ? C1 C2 C3 C4 1.2(4) . . . . ? C2 C3 C4 C5 -2.6(4) . . . . ? C3 C4 C5 C6 1.6(4) . . . . ? C2 C1 C6 C5 -2.1(4) . . . . ? C9 C1 C6 C5 177.5(2) . . . . ? C2 C1 C6 C7 174.6(2) . . . . ? C9 C1 C6 C7 -5.8(3) . . . . ? C4 C5 C6 C1 0.7(4) . . . . ? C4 C5 C6 C7 -175.4(3) . . . . ? C1 C6 C7 O2 130.1(2) . . . . ? C5 C6 C7 O2 -53.5(3) . . . . ? C1 C6 C7 C8 9.8(3) . . . . ? C5 C6 C7 C8 -173.8(2) . . . . ? C1 C6 C7 C10 -109.9(2) . . . . ? C5 C6 C7 C10 66.5(3) . . . . ? O2 C7 C8 C8 54.0(4) . . . 7_566 ? C6 C7 C8 C8 169.8(3) . . . 7_566 ? C10 C7 C8 C8 -71.8(4) . . . 7_566 ? O2 C7 C8 C9 -125.6(2) . . . . ? C6 C7 C8 C9 -9.8(2) . . . . ? C10 C7 C8 C9 108.6(2) . . . . ? C6 C1 C9 O1 179.6(2) . . . . ? C2 C1 C9 O1 -0.8(4) . . . . ? C6 C1 C9 C8 -0.9(3) . . . . ? C2 C1 C9 C8 178.6(2) . . . . ? C8 C8 C9 O1 6.8(5) 7_566 . . . ? C7 C8 C9 O1 -173.6(2) . . . . ? C8 C8 C9 C1 -172.6(3) 7_566 . . . ? C7 C8 C9 C1 7.0(3) . . . . ? O2 C7 C10 C11 174.4(2) . . . . ? C6 C7 C10 C11 56.2(3) . . . . ? C8 C7 C10 C11 -57.8(3) . . . . ? C7 C10 C11 C12 -175.9(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C2 H2A O1 0.93 2.54 3.266(3) 135.1 2 C10 H10A O1 0.97 2.50 3.180(3) 127.4 7_566 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.206 _refine_diff_density_min -0.165 _refine_diff_density_rms 0.041