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
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# TEXT
_publ_section_synopsis
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_publ_section_abstract
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_publ_section_comment
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_publ_section_exptl_prep
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_publ_section_exptl_refinement
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_publ_section_references
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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.
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