Literature DB >> 21581790

{6,6'-Dimeth-oxy-2,2'-[o-phenyl-enebis(nitrilo-methyl-idyne)]diphenolato}cobalt(II) dichloro-methane disolvate.

Atsuhiro Nabei1, Takayoshi Kuroda-Sowa, Takashi Okubo, Masahiko Maekawa, Megumu Munakata.   

Abstract

The title compound, [Co(C(22)H(18)N(2)O(4))]·2CH(2)Cl(2), was isolated from the reaction of N,N'(o-phenyl-ene)bis-(vanillalimine) (H(2)L) with Co(SCN)(2). The crystal structure contains a Co(II) ion surrounded by the L(2-) ligand in a slightly distorted square-planar fashion. Inter-molecular C-H⋯O hydrogen-bonding contacts between the dichloro-methane solvent mol-ecules and the meth-oxy or carboxyl-ate O atoms are observed in the crystal structure. The planar complex mol-ecules stack through inversion related π-π inter-actions 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.

Entities:  

Year:  2009        PMID: 21581790      PMCID: PMC2968184          DOI: 10.1107/S160053680900083X

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN: 1600-5368


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 = 603.19 Monoclinic, 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 F 2 > 2σ(F 2) R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.046 wR(F 2) = 0.089 S = 1.15 5677 reflections 317 parameters H-atom parameters constrained Δρmax = 0.53 e Å−3 Δρmin = −0.66 e Å−3 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. Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680900083X/si2147sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S160053680900083X/si2147Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Co(C22H18N2O4)]·2CH2Cl2F(000) = 1228.00
Mr = 603.19Dx = 1.609 Mg m3
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 mm1
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
Rigaku Mercury diffractometer5100 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 on F2H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.046w = 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 Å3
5677 reflectionsΔρmin = −0.66 e Å3
317 parameters
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).
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*
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)
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)
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 bond lengths (Å)

Co1—O11.8593 (15)
Co1—O21.8611 (14)
Co1—N11.8807 (17)
Co1—N21.8755 (18)
Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯ADAD—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
  1 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

  1 in total
  1 in total

1.  Acetato(aqua){6,6'-dimeth-oxy-2,2'-[ethane-1,2-diylbis(nitrilo-methanylyl-idene)]diphenolato}cobalt(III) methanol disolvate.

Authors:  Gervas Assey; Ray J Butcher; Yilma Gultneh
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-06-23
  1 in total

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