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

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

doi:10.1107/S160053680900083X

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Pages m188-m189

doi:10.1107/S160053680900083X

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

Atsuhiro Nabei,^a Takayoshi Kuroda-Sowa,^a ^* Takashi Okubo,^a Masahiko Maekawa ^a and Megumu Munakata ^a

^aDepartment of Chemistry, Kinki University, 3-4-1, Kowakae, Higashi-Osaka, Osaka 577-8502, Japan
^*Correspondence e-mail: kuroda@chem.kindai.ac.jp

(Received 18 December 2008; accepted 8 January 2009; online 14 January 2009)

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 Co^II 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 π–π 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.

Related literature

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

Experimental

Crystal data

[Co(C₂₂H₁₈N₂O₄)]·2CH₂Cl₂
M_r = 603.19
Monoclinic, P 2₁ /a
a = 13.309 (6) Å
b = 14.088 (6) Å
c = 14.101 (6) Å
β = 109.676 (6)°
V = 2489.4 (19) Å³
Z = 4
Mo Kα radiation
μ = 1.15 mm⁻¹
T = 150 (1) K
0.50 × 0.30 × 0.10 mm

Data collection

Rigaku Mercury diffractometer
Absorption correction: multi-scan (REQAB; Jacobson, 1998 ) T_min = 0.764, T_max = 0.891
28457 measured reflections
5677 independent reflections
5100 reflections with F² > 2σ(F²)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.089
S = 1.15
5677 reflections
317 parameters
H-atom parameters constrained
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.66 e Å⁻³

Table 1
Selected bond lengths (Å)

Co1—O1	1.8593 (15)
Co1—O2	1.8611 (14)
Co1—N1	1.8807 (17)
Co1—N2	1.8755 (18)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C23—H23A⋯O3	0.99	2.54	3.472 (4)	158
C23—H23B⋯O4	0.99	2.33	3.252 (4)	154
C23—H23B⋯O2	0.99	2.41	3.202 (3)	137
C24—H24A⋯O3	0.99	2.35	3.173 (4)	140
C24—H24B⋯O4	0.99	2.38	3.250 (4)	147

Data collection: CrystalClear (Rigaku/MSC, 2007 ); cell refinement: CrystalClear; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680900083X/si2147sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680900083X/si2147Isup2.hkl

checkCIF report

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 Co^II ions is square planar and made up of equatorial planar N₂O₂ coordination from L^2-. 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) Co^II 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.

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

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)]·2CH₂Cl₂	F(000) = 1228.00
M_r = 603.19	D_x = 1.609 Mg m⁻³
Monoclinic, P2₁/a	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2yab	Cell parameters from 6959 reflections
a = 13.309 (6) Å	θ = 3.1–27.5°
b = 14.088 (6) Å	µ = 1.15 mm⁻¹
c = 14.101 (6) Å	T = 150 K
β = 109.676 (6)°	Block, brown
V = 2489.4 (19) Å³	0.50 × 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^-1	R_int = 0.040
ω scans	θ_max = 27.5°
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	h = −17→17
T_min = 0.764, T_max = 0.891	k = −18→17
28457 measured reflections	l = −18→18
5677 independent reflections

Refinement top

Refinement on F²	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.046	w = 1/[σ²(F_o²) + (0.0308P)² + 1.9552P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.089	(Δ/σ)_max < 0.001
S = 1.15	Δρ_max = 0.53 e Å⁻³
5677 reflections	Δρ_min = −0.66 e Å⁻³
317 parameters

Crystal data top

[Co(C₂₂H₁₈N₂O₄)]·2CH₂Cl₂	V = 2489.4 (19) Å³
M_r = 603.19	Z = 4
Monoclinic, P2₁/a	Mo Kα radiation
a = 13.309 (6) Å	µ = 1.15 mm⁻¹
b = 14.088 (6) Å	T = 150 K
c = 14.101 (6) Å	0.50 × 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)
T_min = 0.764, T_max = 0.891	R_int = 0.040
28457 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	317 parameters
wR(F²) = 0.089	H-atom parameters constrained
S = 1.15	Δρ_max = 0.53 e Å⁻³
5677 reflections	Δρ_min = −0.66 e Å⁻³

Special details top

Geometry. The planar Co^II 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

	x	y	z	U_iso*/U_eq
Co1	0.13131 (2)	0.19517 (2)	0.52772 (2)	0.01696 (7)
Cl1	0.44427 (5)	0.14026 (5)	0.68960 (5)	0.03951 (16)
Cl2	0.47220 (7)	0.09420 (8)	0.89664 (6)	0.0672 (2)
Cl3	0.21820 (7)	0.13146 (7)	0.96127 (7)	0.0621 (2)
Cl4	−0.00594 (6)	0.12289 (5)	0.83886 (6)	0.04414 (17)
O1	0.17603 (12)	0.26802 (11)	0.64445 (11)	0.0208 (3)
O2	0.16176 (12)	0.08953 (10)	0.61189 (11)	0.0208 (3)
O3	0.24984 (13)	0.33830 (12)	0.82700 (11)	0.0269 (3)
O4	0.21621 (14)	−0.03363 (12)	0.75913 (12)	0.0310 (3)
N1	0.09468 (14)	0.30090 (13)	0.44144 (13)	0.0186 (3)
N2	0.09571 (14)	0.12300 (13)	0.40921 (13)	0.0186 (3)
C1	0.05949 (17)	0.27635 (16)	0.33749 (16)	0.0202 (4)
C2	0.06502 (17)	0.17945 (16)	0.32009 (16)	0.0207 (4)
C3	0.04319 (19)	0.14651 (18)	0.22208 (17)	0.0277 (5)
C4	0.0107 (2)	0.2098 (2)	0.14228 (18)	0.0329 (5)
C5	−0.00149 (19)	0.3053 (2)	0.15966 (18)	0.0315 (5)
C6	0.02351 (19)	0.33956 (18)	0.25698 (18)	0.0273 (5)
C7	0.10471 (17)	0.39009 (16)	0.46840 (17)	0.0218 (4)
C8	0.14351 (17)	0.42339 (16)	0.56916 (17)	0.0210 (4)
C9	0.14867 (19)	0.52326 (16)	0.58418 (19)	0.0271 (5)
C10	0.1866 (2)	0.56020 (17)	0.6785 (2)	0.0301 (5)
C11	0.22151 (19)	0.49922 (17)	0.76248 (19)	0.0279 (5)
C12	0.21817 (17)	0.40256 (16)	0.74993 (17)	0.0215 (4)
C13	0.17848 (17)	0.36031 (15)	0.65197 (16)	0.0187 (4)
C14	0.2753 (2)	0.3763 (2)	0.92607 (18)	0.0356 (6)
C15	0.09237 (17)	0.03043 (17)	0.40283 (17)	0.0226 (4)
C16	0.12100 (17)	−0.03338 (16)	0.48546 (17)	0.0206 (4)
C17	0.11515 (19)	−0.13206 (16)	0.46470 (19)	0.0261 (5)
C18	0.14356 (19)	−0.19674 (17)	0.5414 (2)	0.0293 (5)
C19	0.17852 (19)	−0.16544 (17)	0.64144 (19)	0.0270 (5)
C20	0.18411 (18)	−0.07012 (16)	0.66371 (17)	0.0227 (4)
C21	0.15525 (17)	0.00007 (15)	0.58599 (16)	0.0193 (4)
C22	0.2476 (2)	−0.09938 (19)	0.84100 (19)	0.0353 (6)
C23	0.38345 (19)	0.14048 (19)	0.78310 (18)	0.0298 (5)
C24	0.1234 (2)	0.1508 (2)	0.8408 (2)	0.0408 (6)
H3	0.0505	0.0810	0.2100	0.033*
H4	−0.0033	0.1877	0.0754	0.039*
H5	−0.0272	0.3476	0.1043	0.038*
H6	0.0162	0.4052	0.2687	0.033*
H7	0.0844	0.4363	0.4164	0.026*
H9	0.1254	0.5646	0.5277	0.033*
H10	0.1896	0.6271	0.6879	0.036*
H11	0.2476	0.5253	0.8284	0.034*
H14A	0.2969	0.3247	0.9754	0.043*
H14B	0.2125	0.4084	0.9323	0.043*
H14C	0.3339	0.4219	0.9385	0.043*
H15	0.0687	0.0036	0.3372	0.027*
H17	0.0912	−0.1534	0.3968	0.031*
H18	0.1396	−0.2628	0.5268	0.035*
H19	0.1986	−0.2106	0.6946	0.032*
H22A	0.2687	−0.0645	0.9049	0.042*
H22B	0.3081	−0.1372	0.8375	0.042*
H22C	0.1877	−0.1415	0.8368	0.042*
H23A	0.3633	0.2061	0.7942	0.036*
H23B	0.3177	0.1015	0.7605	0.036*
H24A	0.1258	0.2182	0.8216	0.049*
H24B	0.1414	0.1111	0.7908	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.02030 (15)	0.01570 (15)	0.01475 (14)	0.00061 (12)	0.00574 (11)	0.00093 (11)
Cl1	0.0392 (3)	0.0514 (4)	0.0337 (3)	0.0015 (3)	0.0199 (2)	0.0022 (3)
Cl2	0.0516 (4)	0.1169 (8)	0.0295 (3)	0.0179 (5)	0.0088 (3)	0.0173 (4)
Cl3	0.0503 (4)	0.0594 (5)	0.0615 (5)	0.0012 (4)	−0.0009 (3)	0.0198 (4)
Cl4	0.0392 (3)	0.0473 (4)	0.0512 (4)	−0.0109 (3)	0.0223 (3)	−0.0102 (3)
O1	0.0281 (8)	0.0165 (7)	0.0177 (7)	0.0011 (6)	0.0075 (6)	0.0001 (6)
O2	0.0258 (8)	0.0177 (7)	0.0178 (7)	−0.0001 (6)	0.0062 (6)	0.0002 (6)
O3	0.0367 (9)	0.0249 (8)	0.0172 (7)	0.0024 (7)	0.0066 (6)	−0.0028 (6)
O4	0.0449 (10)	0.0263 (9)	0.0203 (8)	0.0014 (7)	0.0089 (7)	0.0072 (6)
N1	0.0183 (8)	0.0200 (9)	0.0176 (8)	0.0018 (7)	0.0064 (7)	0.0030 (7)
N2	0.0185 (8)	0.0214 (9)	0.0160 (8)	0.0001 (7)	0.0059 (6)	0.0011 (7)
C1	0.0170 (10)	0.0269 (11)	0.0164 (10)	−0.0008 (8)	0.0050 (8)	0.0029 (8)
C2	0.0172 (10)	0.0277 (12)	0.0168 (10)	−0.0018 (8)	0.0051 (8)	0.0024 (8)
C3	0.0299 (12)	0.0314 (13)	0.0199 (11)	−0.0034 (10)	0.0061 (9)	−0.0020 (9)
C4	0.0300 (13)	0.0490 (16)	0.0174 (11)	−0.0070 (11)	0.0049 (9)	0.0015 (10)
C5	0.0289 (12)	0.0431 (15)	0.0197 (11)	−0.0016 (11)	0.0046 (9)	0.0106 (10)
C6	0.0264 (12)	0.0315 (12)	0.0236 (11)	0.0013 (10)	0.0077 (9)	0.0068 (10)
C7	0.0212 (10)	0.0225 (11)	0.0223 (11)	0.0021 (9)	0.0082 (8)	0.0062 (8)
C8	0.0193 (10)	0.0189 (11)	0.0269 (11)	0.0006 (8)	0.0104 (9)	0.0006 (9)
C9	0.0289 (12)	0.0197 (11)	0.0326 (13)	0.0016 (9)	0.0103 (10)	0.0029 (9)
C10	0.0347 (13)	0.0162 (11)	0.0401 (14)	−0.0005 (10)	0.0135 (11)	−0.0049 (10)
C11	0.0282 (12)	0.0244 (12)	0.0312 (12)	−0.0008 (10)	0.0099 (10)	−0.0094 (10)
C12	0.0205 (10)	0.0224 (11)	0.0230 (10)	0.0011 (9)	0.0090 (8)	−0.0016 (9)
C13	0.0168 (10)	0.0188 (11)	0.0220 (10)	0.0008 (8)	0.0084 (8)	−0.0006 (8)
C14	0.0459 (15)	0.0377 (14)	0.0208 (11)	0.0024 (12)	0.0078 (11)	−0.0074 (10)
C15	0.0211 (11)	0.0250 (11)	0.0224 (11)	−0.0022 (9)	0.0083 (8)	−0.0042 (9)
C16	0.0183 (10)	0.0208 (11)	0.0236 (10)	−0.0014 (8)	0.0084 (8)	−0.0010 (9)
C17	0.0270 (12)	0.0207 (11)	0.0321 (12)	−0.0029 (9)	0.0119 (10)	−0.0066 (9)
C18	0.0299 (13)	0.0179 (11)	0.0429 (14)	−0.0014 (10)	0.0162 (11)	−0.0013 (10)
C19	0.0283 (12)	0.0192 (11)	0.0361 (13)	0.0025 (9)	0.0141 (10)	0.0089 (9)
C20	0.0205 (11)	0.0223 (11)	0.0267 (11)	0.0007 (9)	0.0099 (9)	0.0044 (9)
C21	0.0167 (10)	0.0169 (10)	0.0252 (11)	0.0004 (8)	0.0084 (8)	0.0011 (8)
C22	0.0393 (14)	0.0388 (15)	0.0277 (12)	0.0043 (12)	0.0109 (11)	0.0156 (11)
C23	0.0251 (12)	0.0379 (14)	0.0265 (12)	−0.0005 (10)	0.0090 (9)	−0.0011 (10)
C24	0.0342 (14)	0.0486 (17)	0.0425 (15)	0.0010 (13)	0.0169 (12)	0.0072 (13)

Geometric parameters (Å, º) top

Co1—O1	1.8593 (15)	C12—C13	1.432 (3)
Co1—O2	1.8611 (14)	C15—C16	1.418 (3)
Co1—N1	1.8807 (17)	C16—C17	1.417 (3)
Co1—N2	1.8755 (18)	C16—C21	1.416 (3)
Cl1—C23	1.764 (3)	C17—C18	1.366 (3)
Cl2—C23	1.764 (2)	C18—C19	1.400 (3)
Cl3—C24	1.764 (2)	C19—C20	1.375 (3)
Cl4—C24	1.757 (3)	C20—C21	1.429 (3)
O1—C13	1.304 (2)	C3—H3	0.950
O2—C21	1.307 (2)	C4—H4	0.950
O3—C12	1.367 (2)	C5—H5	0.950
O3—C14	1.426 (2)	C6—H6	0.950
O4—C20	1.367 (2)	C7—H7	0.950
O4—C22	1.428 (3)	C9—H9	0.950
N1—C1	1.423 (2)	C10—H10	0.950
N1—C7	1.306 (2)	C11—H11	0.950
N2—C2	1.426 (2)	C14—H14A	0.980
N2—C15	1.307 (3)	C14—H14B	0.980
C1—C2	1.393 (3)	C14—H14C	0.980
C1—C6	1.395 (3)	C15—H15	0.950
C2—C3	1.393 (3)	C17—H17	0.950
C3—C4	1.386 (3)	C18—H18	0.950
C4—C5	1.386 (3)	C19—H19	0.950
C5—C6	1.386 (3)	C22—H22A	0.980
C7—C8	1.418 (3)	C22—H22B	0.980
C8—C9	1.421 (3)	C22—H22C	0.980
C8—C13	1.416 (3)	C23—H23A	0.990
C9—C10	1.358 (3)	C23—H23B	0.990
C10—C11	1.409 (3)	C24—H24A	0.990
C11—C12	1.372 (3)	C24—H24B	0.990

O1—Co1—O2	86.60 (6)	O2—C21—C20	118.52 (19)
O1—Co1—N1	94.10 (7)	C16—C21—C20	116.76 (19)
O1—Co1—N2	175.97 (8)	Cl1—C23—Cl2	110.01 (14)
O2—Co1—N1	177.70 (7)	Cl3—C24—Cl4	111.07 (18)
O2—Co1—N2	94.02 (7)	C2—C3—H3	120.2
N1—Co1—N2	85.43 (7)	C4—C3—H3	120.2
Co1—O1—C13	127.89 (13)	C3—C4—H4	119.9
Co1—O2—C21	127.82 (13)	C5—C4—H4	119.9
C12—O3—C14	115.96 (18)	C4—C5—H5	119.7
C20—O4—C22	117.44 (18)	C6—C5—H5	119.7
Co1—N1—C1	113.43 (14)	C1—C6—H6	120.5
Co1—N1—C7	126.48 (14)	C5—C6—H6	120.5
C1—N1—C7	119.96 (18)	N1—C7—H7	117.4
Co1—N2—C2	113.23 (14)	C8—C7—H7	117.4
Co1—N2—C15	126.50 (15)	C8—C9—H9	119.7
C2—N2—C15	120.19 (18)	C10—C9—H9	119.7
N1—C1—C2	113.64 (18)	C9—C10—H10	120.1
N1—C1—C6	125.9 (2)	C11—C10—H10	120.1
C2—C1—C6	120.4 (2)	C10—C11—H11	119.7
N2—C2—C1	114.06 (19)	C12—C11—H11	119.7
N2—C2—C3	126.2 (2)	O3—C14—H14A	109.5
C1—C2—C3	119.7 (2)	O3—C14—H14B	109.5
C2—C3—C4	119.7 (2)	O3—C14—H14C	109.5
C3—C4—C5	120.3 (2)	H14A—C14—H14B	109.5
C4—C5—C6	120.7 (2)	H14A—C14—H14C	109.5
C1—C6—C5	119.1 (2)	H14B—C14—H14C	109.5
N1—C7—C8	125.2 (2)	N2—C15—H15	117.2
C7—C8—C9	117.4 (2)	C16—C15—H15	117.2
C7—C8—C13	121.8 (2)	C16—C17—H17	119.7
C9—C8—C13	120.8 (2)	C18—C17—H17	119.7
C8—C9—C10	120.6 (2)	C17—C18—H18	120.1
C9—C10—C11	119.9 (2)	C19—C18—H18	120.1
C10—C11—C12	120.6 (2)	C18—C19—H19	119.6
O3—C12—C11	124.5 (2)	C20—C19—H19	119.6
O3—C12—C13	113.98 (18)	O4—C22—H22A	109.5
C11—C12—C13	121.5 (2)	O4—C22—H22B	109.5
O1—C13—C8	124.51 (19)	O4—C22—H22C	109.5
O1—C13—C12	118.94 (18)	H22A—C22—H22B	109.5
C8—C13—C12	116.54 (19)	H22A—C22—H22C	109.5
N2—C15—C16	125.6 (2)	H22B—C22—H22C	109.5
C15—C16—C17	118.1 (2)	Cl1—C23—H23A	109.7
C15—C16—C21	121.2 (2)	Cl1—C23—H23B	109.7
C17—C16—C21	120.7 (2)	Cl2—C23—H23A	109.7
C16—C17—C18	120.6 (2)	Cl2—C23—H23B	109.7
C17—C18—C19	119.8 (2)	H23A—C23—H23B	108.2
C18—C19—C20	120.8 (2)	Cl3—C24—H24A	109.4
O4—C20—C19	124.5 (2)	Cl3—C24—H24B	109.4
O4—C20—C21	114.12 (19)	Cl4—C24—H24A	109.4
C19—C20—C21	121.4 (2)	Cl4—C24—H24B	109.4
O2—C21—C16	124.72 (19)	H24A—C24—H24B	108.0

O1—Co1—O2—C21	−176.86 (19)	N2—C2—C3—C4	177.9 (2)
O2—Co1—O1—C13	−178.94 (19)	C1—C2—C3—C4	−3.4 (3)
O1—Co1—N1—C1	176.77 (15)	C2—C3—C4—C5	−0.9 (3)
O1—Co1—N1—C7	1.0 (2)	C3—C4—C5—C6	3.2 (4)
N1—Co1—O1—C13	−1.1 (2)	C4—C5—C6—C1	−1.1 (3)
O2—Co1—N2—C2	179.84 (15)	N1—C7—C8—C9	−179.9 (2)
O2—Co1—N2—C15	3.2 (2)	N1—C7—C8—C13	1.7 (3)
N2—Co1—O2—C21	−0.85 (19)	C7—C8—C9—C10	−178.9 (2)
N1—Co1—N2—C2	2.08 (15)	C7—C8—C13—O1	−1.9 (3)
N1—Co1—N2—C15	−174.6 (2)	C7—C8—C13—C12	178.6 (2)
N2—Co1—N1—C1	0.78 (16)	C9—C8—C13—O1	179.8 (2)
N2—Co1—N1—C7	−175.0 (2)	C9—C8—C13—C12	0.3 (3)
Co1—O1—C13—C8	1.8 (3)	C13—C8—C9—C10	−0.5 (3)
Co1—O1—C13—C12	−178.74 (16)	C8—C9—C10—C11	0.2 (3)
Co1—O2—C21—C16	−1.1 (3)	C9—C10—C11—C12	0.4 (4)
Co1—O2—C21—C20	179.16 (16)	C10—C11—C12—O3	−179.6 (2)
C14—O3—C12—C11	7.9 (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—C19	1.1 (3)	O3—C12—C13—C8	179.4 (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—C8	0.3 (3)
Co1—N1—C1—C6	177.4 (2)	N2—C15—C16—C17	−178.4 (2)
Co1—N1—C7—C8	−1.4 (3)	N2—C15—C16—C21	1.2 (3)
C1—N1—C7—C8	−177.0 (2)	C15—C16—C17—C18	178.8 (2)
C7—N1—C1—C2	172.6 (2)	C15—C16—C21—O2	1.3 (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—C3	174.2 (2)	C17—C16—C21—C20	0.7 (3)
Co1—N2—C15—C16	−3.7 (3)	C21—C16—C17—C18	−0.7 (3)
C2—N2—C15—C16	179.8 (2)	C16—C17—C18—C19	0.2 (3)
C15—N2—C2—C1	172.3 (2)	C17—C18—C19—C20	0.4 (4)
C15—N2—C2—C3	−8.9 (3)	C18—C19—C20—O4	179.3 (2)
N1—C1—C2—N2	5.3 (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—C5	175.8 (2)	O4—C20—C21—C16	−179.8 (2)
C2—C1—C6—C5	−3.2 (3)	C19—C20—C21—O2	179.7 (2)
C6—C1—C2—N2	−175.6 (2)	C19—C20—C21—C16	−0.1 (2)
C6—C1—C2—C3	5.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23A···O3	0.99	2.54	3.472 (4)	158
C23—H23B···O4	0.99	2.33	3.252 (4)	154
C23—H23B···O2	0.99	2.41	3.202 (3)	137
C24—H24A···O3	0.99	2.35	3.173 (4)	140
C24—H24B···O4	0.99	2.38	3.250 (4)	147

Experimental details

Crystal data
Chemical formula	[Co(C₂₂H₁₈N₂O₄)]·2CH₂Cl₂
M_r	603.19
Crystal system, space group	Monoclinic, P2₁/a
Temperature (K)	150
a, b, c (Å)	13.309 (6), 14.088 (6), 14.101 (6)
β (°)	109.676 (6)
V (Å³)	2489.4 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.15
Crystal size (mm)	0.50 × 0.30 × 0.10

Data collection
Diffractometer	Rigaku Mercury diffractometer
Absorption correction	Multi-scan (REQAB; Jacobson, 1998)
T_min, T_max	0.764, 0.891
No. of measured, independent and observed [F² > 2σ(F²)] reflections	28457, 5677, 5100
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.089, 1.15
No. of reflections	5677
No. of parameters	317
No. of restraints	?
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.53, −0.66

Computer programs: CrystalClear (Rigaku/MSC, 2007), CrystalStructure (Rigaku/MSC, 2007), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEPII (Johnson, 1976).

Selected bond lengths (Å) top

Co1—O1	1.8593 (15)	Co1—N1	1.8807 (17)
Co1—O2	1.8611 (14)	Co1—N2	1.8755 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23A···O3	0.99	2.54	3.472 (4)	158
C23—H23B···O4	0.99	2.33	3.252 (4)	154
C23—H23B···O2	0.99	2.41	3.202 (3)	137
C24—H24A···O3	0.99	2.35	3.173 (4)	140
C24—H24B···O4	0.99	2.38	3.250 (4)	147

Acknowledgements

Financial support from Kinki University is gratefully acknowledged.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Bella, S. D., Fragala, I., Ledoux, I. & Marks, T. J. (1995). J. Am. Chem. Soc. 117, 9481–9485. CrossRef Web of Science Google Scholar
Cotton, F. A., Wilkinson, G., Murillo, C. A. & Bochmann, M. (1999). Advanced Inorganic Chemistry, 6th ed., ch. 17F. New York: Wiley-Interscience. Google Scholar
Jacobson, R. (1998). REQAB. Iowa State University, USA. Google Scholar
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Liu, J.-M., Peng, X.-G., Liu, J.-H., Zheng, S.-Z., Sun, W. & Xia, C.-G. (2007). Tetrahedron Lett. 48, 929–932. Web of Science CrossRef CAS Google Scholar
Pahor, N. B., Calligaris, M., Delise, P., Dodic, G., Nardin, G. & Randaccio, L. (1976). J. Chem. Soc. Dalton Trans. pp. 2478–2483. CSD CrossRef Web of Science Google Scholar
Rigaku/MSC (2007). CrystalStructure and CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sharghi, H. & Ali Nasseri, M. (2003). Bull. Chem. Soc. Jpn, 76, 137–142. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 65| Part 2| February 2009| Pages m188-m189

doi:10.1107/S160053680900083X

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

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