data_PN_C1_test11_180 _journal_coden_Cambridge ? _publ_requested_journal 'Journal of Physical Chemistry Letters' loop_ _publ_author_name 'Pance Naumov' 'Nobuo Ishizawa' 'Jun Wang' 'Sang Cheol Lee' 'Shunichi Fukuzumi' _publ_contact_author_name 'Pance Naumov' _publ_contact_author_address ; Department of Material and Life Science Graduate School of Engineering, Osaka University, 2-1 Yamada-oka, Suita, Osaka 565-0871 JAPAN ; _publ_contact_author_email npance@wakate.frc.eng.osaka-u.ac.jp _publ_section_title ; Study of the Thermochromism of Polycyclic Overcrowded Enes by High-Temperature X-Ray Diffraction ; _audit_creation_method 'Manual editing of SHELXL-97' _chemical_name_systematic ; 2-(thioxanthen-9-ylidene)indane-1,3-dione ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H12 O2 S' _chemical_formula_sum 'C22 H12 O2 S' _chemical_formula_weight 340.38 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' 'S' 'S' 0.1246 0.1234 '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 9.6444(13) _cell_length_b 8.2160(10) _cell_length_c 21.172(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.206(10) _cell_angle_gamma 90.00 _cell_volume 1673.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 465(2) _exptl_crystal_description 'prism' _exptl_crystal_colour 'red' _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.351 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.205 _exptl_absorpt_correction_type 'empirical' _exptl_absorpt_correction_T_min 0.9640 _exptl_absorpt_correction_T_max 0.9798 _exptl_absorpt_process_details 'APEX2-W2K/NT (Bruker, 2006)' _exptl_special_details ; Thermochromic crystal. Sample heated in capillary. The temperature was corrected by direct measurement. ; _diffrn_ambient_temperature 465(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9532 _diffrn_reflns_av_R_equivalents 0.0880 _diffrn_reflns_av_sigmaI/netI 0.1401 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3693 _reflns_number_gt 1003 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2-W2K/NT (Bruker, 2006)' _computing_cell_refinement 'APEX2-W2K/NT (Bruker, 2006)' _computing_data_reduction 'APEX2-W2K/NT (Bruker, 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 2005)' _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.0458P)^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 SHELXL _refine_ls_extinction_coef 0.0034(11) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3693 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2553 _refine_ls_R_factor_gt 0.0571 _refine_ls_wR_factor_ref 0.1706 _refine_ls_wR_factor_gt 0.1049 _refine_ls_goodness_of_fit_ref 0.942 _refine_ls_restrained_S_all 0.942 _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 S1 S 0.75285(19) 0.72105(17) 0.23148(7) 0.1326(7) Uani 1 1 d . . . O1 O 1.1814(3) 0.7133(4) 0.12495(16) 0.1115(12) Uani 1 1 d . . . O2 O 0.8045(4) 0.8502(5) -0.02015(15) 0.1290(14) Uani 1 1 d . . . C8A C 0.7471(5) 0.9034(6) 0.1226(2) 0.0790(13) Uani 1 1 d . . . C9 C 0.8996(5) 0.8706(4) 0.1241(2) 0.0687(11) Uani 1 1 d . . . C9' C 0.9661(4) 0.8223(5) 0.07293(19) 0.0716(12) Uani 1 1 d . . . C4A C 0.9154(5) 0.8184(6) 0.2393(3) 0.0972(16) Uani 1 1 d . . . C9A' C 1.1047(5) 0.7412(5) 0.0777(2) 0.0814(14) Uani 1 1 d . . . C6' C 1.0202(6) 0.7142(5) -0.0276(2) 0.0792(14) Uani 1 1 d . . . C8 C 0.6789(6) 1.0054(7) 0.0784(2) 0.0959(15) Uani 1 1 d . . . H8 H 0.7287 1.0578 0.0484 0.115 Uiso 1 1 calc R . . C9A C 0.9724(5) 0.8849(5) 0.1871(2) 0.0762(13) Uani 1 1 d . . . C1 C 1.0945(6) 0.9740(6) 0.1962(3) 0.0977(15) Uani 1 1 d . . . H1 H 1.1302 1.0255 0.1618 0.117 Uiso 1 1 calc R . . C10A C 0.6734(6) 0.8361(6) 0.1691(2) 0.0995(16) Uani 1 1 d . . . C1' C 1.1301(5) 0.6793(5) 0.0144(2) 0.0799(13) Uani 1 1 d . . . C5' C 1.0173(6) 0.6683(6) -0.0906(2) 0.1068(17) Uani 1 1 d . . . H5' H 0.9414 0.6917 -0.1188 0.128 Uiso 1 1 calc R . . C8A' C 0.9126(6) 0.8026(6) 0.0055(2) 0.0824(13) Uani 1 1 d . . . C2' C 1.2453(5) 0.5945(5) -0.0051(3) 0.1107(18) Uani 1 1 d . . . H2' H 1.3214 0.5704 0.0229 0.133 Uiso 1 1 calc R . . C5 C 0.5261(8) 0.8540(8) 0.1666(3) 0.135(3) Uani 1 1 d . . . H5 H 0.4737 0.8005 0.1954 0.162 Uiso 1 1 calc R . . C7 C 0.5393(7) 1.0291(8) 0.0787(3) 0.127(2) Uani 1 1 d . . . H7 H 0.4948 1.0996 0.0494 0.152 Uiso 1 1 calc R . . C4' C 1.1318(8) 0.5865(7) -0.1098(3) 0.132(3) Uani 1 1 d . . . H4' H 1.1345 0.5570 -0.1521 0.159 Uiso 1 1 calc R . . C3 C 1.1076(10) 0.9147(11) 0.3057(4) 0.168(4) Uani 1 1 d . . . H3 H 1.1544 0.9222 0.3456 0.201 Uiso 1 1 calc R . . C3' C 1.2402(7) 0.5484(7) -0.0682(3) 0.131(3) Uani 1 1 d . . . H3' H 1.3138 0.4891 -0.0825 0.158 Uiso 1 1 calc R . . C2 C 1.1635(7) 0.9876(8) 0.2551(4) 0.135(2) Uani 1 1 d . . . H2 H 1.2465 1.0452 0.2605 0.162 Uiso 1 1 calc R . . C4 C 0.9862(9) 0.8322(8) 0.2990(3) 0.141(3) Uani 1 1 d . . . H4 H 0.9498 0.7847 0.3341 0.170 Uiso 1 1 calc R . . C6 C 0.4646(8) 0.9515(10) 0.1210(4) 0.150(3) Uani 1 1 d . . . H6 H 0.3686 0.9652 0.1188 0.180 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 S1 0.1924(18) 0.0923(10) 0.1242(12) 0.0023(9) 0.0862(11) -0.0218(11) O1 0.093(3) 0.130(3) 0.110(3) -0.001(2) 0.002(2) 0.024(2) O2 0.117(3) 0.178(4) 0.090(3) -0.014(2) -0.003(2) 0.054(3) C8A 0.082(4) 0.070(3) 0.087(3) -0.012(3) 0.027(3) -0.014(3) C9 0.070(3) 0.062(3) 0.075(3) 0.008(2) 0.014(3) -0.008(2) C9' 0.066(3) 0.074(3) 0.077(3) 0.001(2) 0.020(2) 0.002(3) C4A 0.137(5) 0.084(4) 0.073(3) -0.004(3) 0.027(3) 0.005(3) C9A' 0.087(4) 0.080(3) 0.078(3) 0.004(3) 0.018(3) -0.005(3) C6' 0.100(4) 0.066(3) 0.075(3) 0.005(3) 0.027(3) -0.007(3) C8 0.078(4) 0.106(4) 0.105(4) -0.021(3) 0.016(3) 0.008(3) C9A 0.085(4) 0.069(3) 0.076(3) -0.001(3) 0.014(3) 0.003(3) C1 0.097(4) 0.098(4) 0.096(4) -0.010(3) -0.007(3) 0.005(4) C10A 0.118(5) 0.082(4) 0.104(4) -0.014(3) 0.048(3) -0.017(3) C1' 0.085(4) 0.068(3) 0.091(4) 0.003(3) 0.037(3) -0.008(3) C5' 0.150(5) 0.091(4) 0.084(4) -0.001(3) 0.031(3) -0.002(4) C8A' 0.084(4) 0.084(3) 0.081(4) 0.008(3) 0.018(3) 0.000(3) C2' 0.103(4) 0.097(4) 0.139(5) -0.001(3) 0.052(4) 0.003(3) C5 0.116(7) 0.122(6) 0.176(7) -0.039(5) 0.072(5) -0.037(5) C7 0.086(5) 0.153(6) 0.141(6) -0.052(4) 0.004(4) 0.023(4) C4' 0.194(8) 0.096(5) 0.117(6) -0.004(4) 0.074(5) -0.007(5) C3 0.208(10) 0.191(10) 0.099(6) -0.030(6) -0.023(7) 0.077(7) C3' 0.169(7) 0.094(4) 0.142(7) -0.012(4) 0.091(5) 0.007(4) C2 0.121(5) 0.147(6) 0.130(5) -0.048(5) -0.028(5) 0.020(4) C4 0.216(9) 0.127(6) 0.082(5) 0.005(4) 0.021(6) 0.060(6) C6 0.081(6) 0.178(8) 0.195(9) -0.075(6) 0.043(6) -0.026(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 S1 C10A 1.754(5) . ? S1 C4A 1.757(5) . ? O1 C9A' 1.222(5) . ? O2 C8A' 1.205(5) . ? C8A C10A 1.373(5) . ? C8A C8 1.386(5) . ? C8A C9 1.493(5) . ? C9 C9' 1.359(5) . ? C9 C9A 1.465(5) . ? C9' C9A' 1.491(5) . ? C9' C8A' 1.491(6) . ? C4A C9A 1.381(5) . ? C4A C4 1.396(7) . ? C9A' C1' 1.471(5) . ? C6' C1' 1.363(5) . ? C6' C5' 1.384(6) . ? C6' C8A' 1.484(6) . ? C8 C7 1.360(6) . ? C9A C1 1.388(5) . ? C1 C2 1.373(6) . ? C10A C5 1.425(7) . ? C1' C2' 1.398(6) . ? C5' C4' 1.379(7) . ? C2' C3' 1.387(7) . ? C5 C6 1.358(8) . ? C7 C6 1.350(8) . ? C4' C3' 1.353(7) . ? C3 C4 1.351(8) . ? C3 C2 1.373(8) . ? 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 C10A S1 C4A 99.4(3) . . ? C10A C8A C8 118.9(5) . . ? C10A C8A C9 118.2(5) . . ? C8 C8A C9 122.9(4) . . ? C9' C9 C9A 121.8(4) . . ? C9' C9 C8A 123.8(4) . . ? C9A C9 C8A 114.3(4) . . ? C9 C9' C9A' 123.4(4) . . ? C9 C9' C8A' 130.2(4) . . ? C9A' C9' C8A' 105.2(4) . . ? C9A C4A C4 119.7(6) . . ? C9A C4A S1 120.6(5) . . ? C4 C4A S1 119.7(5) . . ? O1 C9A' C1' 123.4(5) . . ? O1 C9A' C9' 128.7(4) . . ? C1' C9A' C9' 107.5(4) . . ? C1' C6' C5' 122.1(5) . . ? C1' C6' C8A' 109.4(4) . . ? C5' C6' C8A' 128.5(5) . . ? C7 C8 C8A 120.3(5) . . ? C4A C9A C1 118.7(5) . . ? C4A C9A C9 120.3(5) . . ? C1 C9A C9 120.9(4) . . ? C2 C1 C9A 121.2(6) . . ? C8A C10A C5 120.0(5) . . ? C8A C10A S1 122.5(5) . . ? C5 C10A S1 117.5(5) . . ? C6' C1' C2' 120.7(5) . . ? C6' C1' C9A' 110.4(4) . . ? C2' C1' C9A' 129.0(6) . . ? C4' C5' C6' 117.2(5) . . ? O2 C8A' C6' 124.0(5) . . ? O2 C8A' C9' 128.5(5) . . ? C6' C8A' C9' 107.5(4) . . ? C3' C2' C1' 116.5(5) . . ? C6 C5 C10A 118.0(7) . . ? C6 C7 C8 120.8(7) . . ? C3' C4' C5' 121.1(7) . . ? C4 C3 C2 121.6(9) . . ? C4' C3' C2' 122.4(7) . . ? C3 C2 C1 118.8(8) . . ? C3 C4 C4A 119.9(8) . . ? C7 C6 C5 121.6(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 C10A C8A C9 C9' 132.1(4) . . . . ? C8 C8A C9 C9' -51.4(6) . . . . ? C10A C8A C9 C9A -44.2(5) . . . . ? C8 C8A C9 C9A 132.3(4) . . . . ? C9A C9 C9' C9A' 15.8(6) . . . . ? C8A C9 C9' C9A' -160.3(4) . . . . ? C9A C9 C9' C8A' -178.9(4) . . . . ? C8A C9 C9' C8A' 5.0(7) . . . . ? C10A S1 C4A C9A -31.9(4) . . . . ? C10A S1 C4A C4 146.5(4) . . . . ? C9 C9' C9A' O1 -4.0(7) . . . . ? C8A' C9' C9A' O1 -172.4(5) . . . . ? C9 C9' C9A' C1' 169.2(4) . . . . ? C8A' C9' C9A' C1' 0.8(4) . . . . ? C10A C8A C8 C7 -4.4(7) . . . . ? C9 C8A C8 C7 179.1(4) . . . . ? C4 C4A C9A C1 -4.5(7) . . . . ? S1 C4A C9A C1 173.9(3) . . . . ? C4 C4A C9A C9 179.7(4) . . . . ? S1 C4A C9A C9 -1.8(6) . . . . ? C9' C9 C9A C4A -132.5(4) . . . . ? C8A C9 C9A C4A 44.0(5) . . . . ? C9' C9 C9A C1 51.8(6) . . . . ? C8A C9 C9A C1 -131.7(4) . . . . ? C4A C9A C1 C2 4.4(7) . . . . ? C9 C9A C1 C2 -179.8(4) . . . . ? C8 C8A C10A C5 8.1(7) . . . . ? C9 C8A C10A C5 -175.2(4) . . . . ? C8 C8A C10A S1 -173.9(3) . . . . ? C9 C8A C10A S1 2.7(6) . . . . ? C4A S1 C10A C8A 31.6(4) . . . . ? C4A S1 C10A C5 -150.4(4) . . . . ? C5' C6' C1' C2' -0.1(7) . . . . ? C8A' C6' C1' C2' 179.4(4) . . . . ? C5' C6' C1' C9A' -179.6(4) . . . . ? C8A' C6' C1' C9A' -0.1(5) . . . . ? O1 C9A' C1' C6' 173.2(4) . . . . ? C9' C9A' C1' C6' -0.4(5) . . . . ? O1 C9A' C1' C2' -6.3(7) . . . . ? C9' C9A' C1' C2' -179.9(4) . . . . ? C1' C6' C5' C4' -0.7(7) . . . . ? C8A' C6' C5' C4' 179.9(4) . . . . ? C1' C6' C8A' O2 179.3(5) . . . . ? C5' C6' C8A' O2 -1.3(8) . . . . ? C1' C6' C8A' C9' 0.6(5) . . . . ? C5' C6' C8A' C9' -179.9(4) . . . . ? C9 C9' C8A' O2 13.2(8) . . . . ? C9A' C9' C8A' O2 -179.4(5) . . . . ? C9 C9' C8A' C6' -168.2(4) . . . . ? C9A' C9' C8A' C6' -0.9(4) . . . . ? C6' C1' C2' C3' -0.4(7) . . . . ? C9A' C1' C2' C3' 179.0(4) . . . . ? C8A C10A C5 C6 -6.2(9) . . . . ? S1 C10A C5 C6 175.8(5) . . . . ? C8A C8 C7 C6 -1.4(8) . . . . ? C6' C5' C4' C3' 2.1(8) . . . . ? C5' C4' C3' C2' -2.7(10) . . . . ? C1' C2' C3' C4' 1.8(9) . . . . ? C4 C3 C2 C1 -0.8(11) . . . . ? C9A C1 C2 C3 -1.7(9) . . . . ? C2 C3 C4 C4A 0.7(12) . . . . ? C9A C4A C4 C3 2.1(10) . . . . ? S1 C4A C4 C3 -176.4(6) . . . . ? C8 C7 C6 C5 3.4(10) . . . . ? C10A C5 C6 C7 0.4(11) . . . . ? C9A C9 C9' C8A 176.1(6) . . . . ? C9A' C9 C9' C8A' 165.3(7) . . . . ? _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.960 _refine_diff_density_max 0.168 _refine_diff_density_min -0.150 _refine_diff_density_rms 0.034 #====================================================================== # TEXT _publ_section_synopsis ; ; _publ_section_abstract ; ; _publ_section_comment ; ; _publ_section_exptl_prep ; ; _publ_section_exptl_refinement ; ; _publ_section_references ; APEX2-W2K/NT, v1.0; Bruker Analytical X-ray Systems Inc.: Madison, WI, 2006. Sheldrick, G. M. (2008). Acta Cryst. A64, 112--122. Brandenburg, K (2005). DIAMOND (Version 3.1). Crystal Impact GbR, Bonn, Germany. Farrugia, L. J. (1999). Win-GX (Version 1.70.01). J. Appl. Cryst.32, 837--838. ; #======================================================================