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Acta Cryst. (2009). E65, m188-m189    [ doi:10.1107/S160053680900083X ]

{6,6'-Dimethoxy-2,2'-[o-phenylenebis(nitrilomethylidyne)]diphenolato}cobalt(II) dichloromethane disolvate

A. Nabei, T. Kuroda-Sowa, T. Okubo, M. Maekawa and M. Munakata

Abstract top

The title compound, [Co(C22H18N2O4)]·2CH2Cl2, was isolated from the reaction of N,N'(o-phenylene)bis(vanillalimine) (H2L) with Co(SCN)2. The crystal structure contains a CoII ion surrounded by the L2- ligand in a slightly distorted square-planar fashion. Intermolecular C-H...O hydrogen-bonding contacts between the dichloromethane solvent molecules and the methoxy or carboxylate O atoms are observed in the crystal structure. The planar complex molecules stack through inversion related [pi]-[pi] interactions between the six-membered rings of the vanillalimine half ligands. The distance between centroids is 3.498 (2) Å and the perpendicular distance is 3.345 Å. A partial stacking is observed with a centroid-centroid distance of 3.830 (2) Å, a perpendicular distance of 3.350 Å and a slippage of 1.856 Å.

Comment top

Cobalt–Schiff base complexes are thoroughly investigated in their catalytic oxidation, chiral synthesis in solution, and so on (Cotton et al., 1999; Liu et al., 2007; Sharghi et al., 2003). However, a relatively few works are devoted to their solid state properties such as magnetic or conductive properties (Bella et al., 1995). Our interest on the cobalt-salophen system is based on their planar structure (Pahor et al., 1976) together with its redox-active characteristics, which implies their potential application for conducting and/or magnetic devices. In this work the structure of the title molecule, [Co(C22H18N2O4)].2(CH2Cl2) is reported (Fig. 1) The coordination sphere around CoII ions is square planar and made up of equatorial planar N2O2 coordination from L2-. The Co—O and Co—N bond distances are given in Table 1. The Co—N distances are comparable to those of low spin (LS) CoII species, representing a characteristic feature of the LS state. Intermolecular C—H···O hydrogen bonding contacts are observed in the title structure (Table 2) between methoxy oxygen atoms and the dichloromethane donors. The planar molecules stack each other through inversion related π···π interactions, with the centroids Cg3···Cg6i distance of 3.498 (2) Å, the perpendicular distance of the centroid Cg3 and the plane of Cg6 is 3.345 Å; a partial stacking is also observed between inversion related Cg3 rings: Cg3···Cg3i = 3.830 (2) Å, the perpendicular distance is 3.350 Å, the slippage between rings is 1.856 Å, symmetry code i = -x, -y, 1 - z. definitions: Cg3 is the centroid of the ring Co, O2, C21, C16, C15, N2 Cg6 is the centroid of the ring C16 - C21

Related literature top

For general background, see: Cotton et al. (1999); Liu et al. (2007); Sharghi et al.(2003). For related structures, see: Pahor et al.(1976). For related properties, see: Bella et al. (1995).

Experimental top

To a dichloromethane solution (10 ml) containing H2L (0.1 mmol, 42.7 mg) placed at the bottom of a glass tube, a methanol solution (10 ml) containing Co(SCN)2 (0.1 mmol, 17.6 mg) was added quietly. After standing for two weeks at room temperature, brown brick crystals of (I) suitable for X-ray analysis were obtained.

Refinement top

All H atoms were positioned geometrically and treated as riding [C—H = 0.95 Å, 0.98 Å and 0.99 Å, and Uiso(H)= 1.2Ueq(C)].

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2007); cell refinement: CrystalClear (Rigaku/MSC, 2007); data reduction: CrystalStructure (Rigaku/MSC, 2007); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2007).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with the atom-numbering scheme, showing 50% probability displacement ellipsoids.
{6,6'-Dimethoxy-2,2'-[o- phenylenebis(nitrilomethylidyne)]diphenolato}cobalt(II) dichloromethane disolvate top
Crystal data top
[Co(C22H18N2O4)]·2CH2Cl2F(000) = 1228.00
Mr = 603.19Dx = 1.609 Mg m−3
Monoclinic, P21/aMo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2yabCell parameters from 6959 reflections
a = 13.309 (6) Åθ = 3.1–27.5°
b = 14.088 (6) ŵ = 1.15 mm−1
c = 14.101 (6) ÅT = 150 K
β = 109.676 (6)°Block, brown
V = 2489.4 (19) Å30.50 × 0.30 × 0.10 mm
Z = 4
Data collection top
Rigaku Mercury
diffractometer		5100 reflections with F2 > 2σ(F2)
Detector resolution: 7.31 pixels mm-1Rint = 0.040
ω scansθmax = 27.5°
Absorption correction: multi-scan
(REQAB; Jacobson, 1998)		h = −17→17
Tmin = 0.764, Tmax = 0.891k = −18→17
28457 measured reflectionsl = −18→18
5677 independent reflections
Refinement top
Refinement on F2H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.046 w = 1/[σ2(Fo2) + (0.0308P)2 + 1.9552P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.089(Δ/σ)max < 0.001
S = 1.15Δρmax = 0.53 e Å−3
5677 reflectionsΔρmin = −0.66 e Å−3
317 parameters
Crystal data top
[Co(C22H18N2O4)]·2CH2Cl2V = 2489.4 (19) Å3
Mr = 603.19Z = 4
Monoclinic, P21/aMo Kα radiation
a = 13.309 (6) ŵ = 1.15 mm−1
b = 14.088 (6) ÅT = 150 K
c = 14.101 (6) Å0.50 × 0.30 × 0.10 mm
β = 109.676 (6)°
Data collection top
Rigaku Mercury
diffractometer		5677 independent reflections
Absorption correction: multi-scan
(REQAB; Jacobson, 1998)		5100 reflections with F2 > 2σ(F2)
Tmin = 0.764, Tmax = 0.891Rint = 0.040
28457 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.089Δρmax = 0.53 e Å−3
S = 1.15Δρmin = −0.66 e Å−3
5677 reflectionsAbsolute structure: ?
317 parametersFlack parameter: ?
? restraintsRogers parameter: ?
Special details top

Geometry. The planar CoII complex has non-crystallographic mm2 symmetry.

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Co10.13131 (2)0.19517 (2)0.52772 (2)0.01696 (7)
Cl10.44427 (5)0.14026 (5)0.68960 (5)0.03951 (16)
Cl20.47220 (7)0.09420 (8)0.89664 (6)0.0672 (2)
Cl30.21820 (7)0.13146 (7)0.96127 (7)0.0621 (2)
Cl4−0.00594 (6)0.12289 (5)0.83886 (6)0.04414 (17)
O10.17603 (12)0.26802 (11)0.64445 (11)0.0208 (3)
O20.16176 (12)0.08953 (10)0.61189 (11)0.0208 (3)
O30.24984 (13)0.33830 (12)0.82700 (11)0.0269 (3)
O40.21621 (14)−0.03363 (12)0.75913 (12)0.0310 (3)
N10.09468 (14)0.30090 (13)0.44144 (13)0.0186 (3)
N20.09571 (14)0.12300 (13)0.40921 (13)0.0186 (3)
C10.05949 (17)0.27635 (16)0.33749 (16)0.0202 (4)
C20.06502 (17)0.17945 (16)0.32009 (16)0.0207 (4)
C30.04319 (19)0.14651 (18)0.22208 (17)0.0277 (5)
C40.0107 (2)0.2098 (2)0.14228 (18)0.0329 (5)
C5−0.00149 (19)0.3053 (2)0.15966 (18)0.0315 (5)
C60.02351 (19)0.33956 (18)0.25698 (18)0.0273 (5)
C70.10471 (17)0.39009 (16)0.46840 (17)0.0218 (4)
C80.14351 (17)0.42339 (16)0.56916 (17)0.0210 (4)
C90.14867 (19)0.52326 (16)0.58418 (19)0.0271 (5)
C100.1866 (2)0.56020 (17)0.6785 (2)0.0301 (5)
C110.22151 (19)0.49922 (17)0.76248 (19)0.0279 (5)
C120.21817 (17)0.40256 (16)0.74993 (17)0.0215 (4)
C130.17848 (17)0.36031 (15)0.65197 (16)0.0187 (4)
C140.2753 (2)0.3763 (2)0.92607 (18)0.0356 (6)
C150.09237 (17)0.03043 (17)0.40283 (17)0.0226 (4)
C160.12100 (17)−0.03338 (16)0.48546 (17)0.0206 (4)
C170.11515 (19)−0.13206 (16)0.46470 (19)0.0261 (5)
C180.14356 (19)−0.19674 (17)0.5414 (2)0.0293 (5)
C190.17852 (19)−0.16544 (17)0.64144 (19)0.0270 (5)
C200.18411 (18)−0.07012 (16)0.66371 (17)0.0227 (4)
C210.15525 (17)0.00007 (15)0.58599 (16)0.0193 (4)
C220.2476 (2)−0.09938 (19)0.84100 (19)0.0353 (6)
C230.38345 (19)0.14048 (19)0.78310 (18)0.0298 (5)
C240.1234 (2)0.1508 (2)0.8408 (2)0.0408 (6)
H30.05050.08100.21000.033*
H4−0.00330.18770.07540.039*
H5−0.02720.34760.10430.038*
H60.01620.40520.26870.033*
H70.08440.43630.41640.026*
H90.12540.56460.52770.033*
H100.18960.62710.68790.036*
H110.24760.52530.82840.034*
H14A0.29690.32470.97540.043*
H14B0.21250.40840.93230.043*
H14C0.33390.42190.93850.043*
H150.06870.00360.33720.027*
H170.0912−0.15340.39680.031*
H180.1396−0.26280.52680.035*
H190.1986−0.21060.69460.032*
H22A0.2687−0.06450.90490.042*
H22B0.3081−0.13720.83750.042*
H22C0.1877−0.14150.83680.042*
H23A0.36330.20610.79420.036*
H23B0.31770.10150.76050.036*
H24A0.12580.21820.82160.049*
H24B0.14140.11110.79080.049*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.02030 (15)0.01570 (15)0.01475 (14)0.00061 (12)0.00574 (11)0.00093 (11)
Cl10.0392 (3)0.0514 (4)0.0337 (3)0.0015 (3)0.0199 (2)0.0022 (3)
Cl20.0516 (4)0.1169 (8)0.0295 (3)0.0179 (5)0.0088 (3)0.0173 (4)
Cl30.0503 (4)0.0594 (5)0.0615 (5)0.0012 (4)−0.0009 (3)0.0198 (4)
Cl40.0392 (3)0.0473 (4)0.0512 (4)−0.0109 (3)0.0223 (3)−0.0102 (3)
O10.0281 (8)0.0165 (7)0.0177 (7)0.0011 (6)0.0075 (6)0.0001 (6)
O20.0258 (8)0.0177 (7)0.0178 (7)−0.0001 (6)0.0062 (6)0.0002 (6)
O30.0367 (9)0.0249 (8)0.0172 (7)0.0024 (7)0.0066 (6)−0.0028 (6)
O40.0449 (10)0.0263 (9)0.0203 (8)0.0014 (7)0.0089 (7)0.0072 (6)
N10.0183 (8)0.0200 (9)0.0176 (8)0.0018 (7)0.0064 (7)0.0030 (7)
N20.0185 (8)0.0214 (9)0.0160 (8)0.0001 (7)0.0059 (6)0.0011 (7)
C10.0170 (10)0.0269 (11)0.0164 (10)−0.0008 (8)0.0050 (8)0.0029 (8)
C20.0172 (10)0.0277 (12)0.0168 (10)−0.0018 (8)0.0051 (8)0.0024 (8)
C30.0299 (12)0.0314 (13)0.0199 (11)−0.0034 (10)0.0061 (9)−0.0020 (9)
C40.0300 (13)0.0490 (16)0.0174 (11)−0.0070 (11)0.0049 (9)0.0015 (10)
C50.0289 (12)0.0431 (15)0.0197 (11)−0.0016 (11)0.0046 (9)0.0106 (10)
C60.0264 (12)0.0315 (12)0.0236 (11)0.0013 (10)0.0077 (9)0.0068 (10)
C70.0212 (10)0.0225 (11)0.0223 (11)0.0021 (9)0.0082 (8)0.0062 (8)
C80.0193 (10)0.0189 (11)0.0269 (11)0.0006 (8)0.0104 (9)0.0006 (9)
C90.0289 (12)0.0197 (11)0.0326 (13)0.0016 (9)0.0103 (10)0.0029 (9)
C100.0347 (13)0.0162 (11)0.0401 (14)−0.0005 (10)0.0135 (11)−0.0049 (10)
C110.0282 (12)0.0244 (12)0.0312 (12)−0.0008 (10)0.0099 (10)−0.0094 (10)
C120.0205 (10)0.0224 (11)0.0230 (10)0.0011 (9)0.0090 (8)−0.0016 (9)
C130.0168 (10)0.0188 (11)0.0220 (10)0.0008 (8)0.0084 (8)−0.0006 (8)
C140.0459 (15)0.0377 (14)0.0208 (11)0.0024 (12)0.0078 (11)−0.0074 (10)
C150.0211 (11)0.0250 (11)0.0224 (11)−0.0022 (9)0.0083 (8)−0.0042 (9)
C160.0183 (10)0.0208 (11)0.0236 (10)−0.0014 (8)0.0084 (8)−0.0010 (9)
C170.0270 (12)0.0207 (11)0.0321 (12)−0.0029 (9)0.0119 (10)−0.0066 (9)
C180.0299 (13)0.0179 (11)0.0429 (14)−0.0014 (10)0.0162 (11)−0.0013 (10)
C190.0283 (12)0.0192 (11)0.0361 (13)0.0025 (9)0.0141 (10)0.0089 (9)
C200.0205 (11)0.0223 (11)0.0267 (11)0.0007 (9)0.0099 (9)0.0044 (9)
C210.0167 (10)0.0169 (10)0.0252 (11)0.0004 (8)0.0084 (8)0.0011 (8)
C220.0393 (14)0.0388 (15)0.0277 (12)0.0043 (12)0.0109 (11)0.0156 (11)
C230.0251 (12)0.0379 (14)0.0265 (12)−0.0005 (10)0.0090 (9)−0.0011 (10)
C240.0342 (14)0.0486 (17)0.0425 (15)0.0010 (13)0.0169 (12)0.0072 (13)
Geometric parameters (Å, °) top
Co1—O11.8593 (15)C12—C131.432 (3)
Co1—O21.8611 (14)C15—C161.418 (3)
Co1—N11.8807 (17)C16—C171.417 (3)
Co1—N21.8755 (18)C16—C211.416 (3)
Cl1—C231.764 (3)C17—C181.366 (3)
Cl2—C231.764 (2)C18—C191.400 (3)
Cl3—C241.764 (2)C19—C201.375 (3)
Cl4—C241.757 (3)C20—C211.429 (3)
O1—C131.304 (2)C3—H30.950
O2—C211.307 (2)C4—H40.950
O3—C121.367 (2)C5—H50.950
O3—C141.426 (2)C6—H60.950
O4—C201.367 (2)C7—H70.950
O4—C221.428 (3)C9—H90.950
N1—C11.423 (2)C10—H100.950
N1—C71.306 (2)C11—H110.950
N2—C21.426 (2)C14—H14A0.980
N2—C151.307 (3)C14—H14B0.980
C1—C21.393 (3)C14—H14C0.980
C1—C61.395 (3)C15—H150.950
C2—C31.393 (3)C17—H170.950
C3—C41.386 (3)C18—H180.950
C4—C51.386 (3)C19—H190.950
C5—C61.386 (3)C22—H22A0.980
C7—C81.418 (3)C22—H22B0.980
C8—C91.421 (3)C22—H22C0.980
C8—C131.416 (3)C23—H23A0.990
C9—C101.358 (3)C23—H23B0.990
C10—C111.409 (3)C24—H24A0.990
C11—C121.372 (3)C24—H24B0.990
O1—Co1—O286.60 (6)O2—C21—C20118.52 (19)
O1—Co1—N194.10 (7)C16—C21—C20116.76 (19)
O1—Co1—N2175.97 (8)Cl1—C23—Cl2110.01 (14)
O2—Co1—N1177.70 (7)Cl3—C24—Cl4111.07 (18)
O2—Co1—N294.02 (7)C2—C3—H3120.2
N1—Co1—N285.43 (7)C4—C3—H3120.2
Co1—O1—C13127.89 (13)C3—C4—H4119.9
Co1—O2—C21127.82 (13)C5—C4—H4119.9
C12—O3—C14115.96 (18)C4—C5—H5119.7
C20—O4—C22117.44 (18)C6—C5—H5119.7
Co1—N1—C1113.43 (14)C1—C6—H6120.5
Co1—N1—C7126.48 (14)C5—C6—H6120.5
C1—N1—C7119.96 (18)N1—C7—H7117.4
Co1—N2—C2113.23 (14)C8—C7—H7117.4
Co1—N2—C15126.50 (15)C8—C9—H9119.7
C2—N2—C15120.19 (18)C10—C9—H9119.7
N1—C1—C2113.64 (18)C9—C10—H10120.1
N1—C1—C6125.9 (2)C11—C10—H10120.1
C2—C1—C6120.4 (2)C10—C11—H11119.7
N2—C2—C1114.06 (19)C12—C11—H11119.7
N2—C2—C3126.2 (2)O3—C14—H14A109.5
C1—C2—C3119.7 (2)O3—C14—H14B109.5
C2—C3—C4119.7 (2)O3—C14—H14C109.5
C3—C4—C5120.3 (2)H14A—C14—H14B109.5
C4—C5—C6120.7 (2)H14A—C14—H14C109.5
C1—C6—C5119.1 (2)H14B—C14—H14C109.5
N1—C7—C8125.2 (2)N2—C15—H15117.2
C7—C8—C9117.4 (2)C16—C15—H15117.2
C7—C8—C13121.8 (2)C16—C17—H17119.7
C9—C8—C13120.8 (2)C18—C17—H17119.7
C8—C9—C10120.6 (2)C17—C18—H18120.1
C9—C10—C11119.9 (2)C19—C18—H18120.1
C10—C11—C12120.6 (2)C18—C19—H19119.6
O3—C12—C11124.5 (2)C20—C19—H19119.6
O3—C12—C13113.98 (18)O4—C22—H22A109.5
C11—C12—C13121.5 (2)O4—C22—H22B109.5
O1—C13—C8124.51 (19)O4—C22—H22C109.5
O1—C13—C12118.94 (18)H22A—C22—H22B109.5
C8—C13—C12116.54 (19)H22A—C22—H22C109.5
N2—C15—C16125.6 (2)H22B—C22—H22C109.5
C15—C16—C17118.1 (2)Cl1—C23—H23A109.7
C15—C16—C21121.2 (2)Cl1—C23—H23B109.7
C17—C16—C21120.7 (2)Cl2—C23—H23A109.7
C16—C17—C18120.6 (2)Cl2—C23—H23B109.7
C17—C18—C19119.8 (2)H23A—C23—H23B108.2
C18—C19—C20120.8 (2)Cl3—C24—H24A109.4
O4—C20—C19124.5 (2)Cl3—C24—H24B109.4
O4—C20—C21114.12 (19)Cl4—C24—H24A109.4
C19—C20—C21121.4 (2)Cl4—C24—H24B109.4
O2—C21—C16124.72 (19)H24A—C24—H24B108.0
O1—Co1—O2—C21−176.86 (19)N2—C2—C3—C4177.9 (2)
O2—Co1—O1—C13−178.94 (19)C1—C2—C3—C4−3.4 (3)
O1—Co1—N1—C1176.77 (15)C2—C3—C4—C5−0.9 (3)
O1—Co1—N1—C71.0 (2)C3—C4—C5—C63.2 (4)
N1—Co1—O1—C13−1.1 (2)C4—C5—C6—C1−1.1 (3)
O2—Co1—N2—C2179.84 (15)N1—C7—C8—C9−179.9 (2)
O2—Co1—N2—C153.2 (2)N1—C7—C8—C131.7 (3)
N2—Co1—O2—C21−0.85 (19)C7—C8—C9—C10−178.9 (2)
N1—Co1—N2—C22.08 (15)C7—C8—C13—O1−1.9 (3)
N1—Co1—N2—C15−174.6 (2)C7—C8—C13—C12178.6 (2)
N2—Co1—N1—C10.78 (16)C9—C8—C13—O1179.8 (2)
N2—Co1—N1—C7−175.0 (2)C9—C8—C13—C120.3 (3)
Co1—O1—C13—C81.8 (3)C13—C8—C9—C10−0.5 (3)
Co1—O1—C13—C12−178.74 (16)C8—C9—C10—C110.2 (3)
Co1—O2—C21—C16−1.1 (3)C9—C10—C11—C120.4 (4)
Co1—O2—C21—C20179.16 (16)C10—C11—C12—O3−179.6 (2)
C14—O3—C12—C117.9 (3)C10—C11—C12—C13−0.6 (3)
C14—O3—C12—C13−171.2 (2)O3—C12—C13—O1−0.1 (2)
C22—O4—C20—C191.1 (3)O3—C12—C13—C8179.4 (2)
C22—O4—C20—C21−179.3 (2)C11—C12—C13—O1−179.3 (2)
Co1—N1—C1—C2−3.6 (2)C11—C12—C13—C80.3 (3)
Co1—N1—C1—C6177.4 (2)N2—C15—C16—C17−178.4 (2)
Co1—N1—C7—C8−1.4 (3)N2—C15—C16—C211.2 (3)
C1—N1—C7—C8−177.0 (2)C15—C16—C17—C18178.8 (2)
C7—N1—C1—C2172.6 (2)C15—C16—C21—O21.3 (3)
C7—N1—C1—C6−6.5 (3)C15—C16—C21—C20−178.9 (2)
Co1—N2—C2—C1−4.6 (2)C17—C16—C21—O2−179.1 (2)
Co1—N2—C2—C3174.2 (2)C17—C16—C21—C200.7 (3)
Co1—N2—C15—C16−3.7 (3)C21—C16—C17—C18−0.7 (3)
C2—N2—C15—C16179.8 (2)C16—C17—C18—C190.2 (3)
C15—N2—C2—C1172.3 (2)C17—C18—C19—C200.4 (4)
C15—N2—C2—C3−8.9 (3)C18—C19—C20—O4179.3 (2)
N1—C1—C2—N25.3 (2)C18—C19—C20—C21−0.4 (3)
N1—C1—C2—C3−173.6 (2)O4—C20—C21—O2−0.0 (2)
N1—C1—C6—C5175.8 (2)O4—C20—C21—C16−179.8 (2)
C2—C1—C6—C5−3.2 (3)C19—C20—C21—O2179.7 (2)
C6—C1—C2—N2−175.6 (2)C19—C20—C21—C16−0.1 (2)
C6—C1—C2—C35.5 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C23—H23A···O30.992.543.472 (4)158
C23—H23B···O40.992.333.252 (4)154
C23—H23B···O20.992.413.202 (3)137
C24—H24A···O30.992.353.173 (4)140
C24—H24B···O40.992.383.250 (4)147
Table 1
Selected geometric parameters (Å) top
Co1—O11.8593 (15)Co1—N11.8807 (17)
Co1—O21.8611 (14)Co1—N21.8755 (18)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C23—H23A···O30.992.543.472 (4)158
C23—H23B···O40.992.333.252 (4)154
C23—H23B···O20.992.413.202 (3)137
C24—H24A···O30.992.353.173 (4)140
C24—H24B···O40.992.383.250 (4)147
Acknowledgements top

Financial support from Kinki University is gratefully acknowledged.

references
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