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Acta Crystallogr Sect E Struct Rep Online. 2008 November 1; 64(Pt 11): m1445.
Published online 2008 October 18. doi:  10.1107/S1600536808033527
PMCID: PMC2959620

catena-Poly[[{2-meth­oxy-6-[(4-methyl­phen­yl)imino­meth­yl]phenolato}­cad­mium(II)]-di-μ2-chlorido-[dimethanol­cadmium(II)]-di-μ2-chlorido-[{2-meth­oxy-6-[(4-methyl­phen­yl)imino­meth­yl]­phenolato}cadmium(II)]-di-μ2-chlorido]

Abstract

The structure of the title compound, [Cd3Cl6(C15H15NO2)2(CH4O)2]n, is based on a layered zigzag polymeric chain along the c axis. The CdII ions are linked by double chlorine bridges alternating between one CdCl4(CH3OH)2 and two CdCl4(C15H15NO2) octa­hedral coordination units. Additional intrachain N—H(...)O and O—H(...)Cl hydrogen-bond interactions stabilize this arrangement.

Related literature

For related literature, see: Henkel & Krebs (2004 [triangle]); Suen & Wang (2007 [triangle]); Wang et al. (2005 [triangle]); Zhang & Bu (2008 [triangle]); De Girolamo et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-m1445-scheme1.jpg

Experimental

Crystal data

  • [Cd3Cl6(C15H15NO2)2(CH4O)2]
  • M r = 1096.57
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-m1445-efi1.jpg
  • a = 19.7697 (5) Å
  • b = 13.9554 (3) Å
  • c = 15.1449 (4) Å
  • β = 110.4230 (10)°
  • V = 3915.74 (17) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 2.07 mm−1
  • T = 296 (2) K
  • 0.15 × 0.13 × 0.05 mm

Data collection

  • Bruker APEXII area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.736, T max = 0.898
  • 13592 measured reflections
  • 3350 independent reflections
  • 2773 reflections with I > 2σ(I)
  • R int = 0.033

Refinement

  • R[F 2 > 2σ(F 2)] = 0.026
  • wR(F 2) = 0.060
  • S = 1.05
  • 3350 reflections
  • 226 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.36 e Å−3
  • Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2006 [triangle]); cell refinement: SAINT (Bruker, 2006 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808033527/at2645sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808033527/at2645Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

There has been an increasing interest in the coordination chemistry of cadmium in recent years due to the increased recognition of its role in biological organisms (Henkel & Krebs, 2004), as well as in molecular-based materials (De Girolamo et al., 2007). In the quest for molecular-based materials with interesting properties, much attention has been given to one-, two- and three-dimensional extended solids which involve cadmium (Suen & Wang, 2007; Wang et al., 2005; Zhang & Bu, 2008). Complexes of the type CdX2 (X = CI or Br) with organic bases typically form one- or two-dimensional halogen-bridged chain compounds with six-coordination octahedral cadmium(II). Here, we describe the synthesis and crystal structure of the cadmium(II) chloride complex with 2-[(4-methylphenylimino)methyl]-6-methoxyphenol.

The crystal structure of the title compound (I) has features of the monoclinic space group C2/c. As illustrated in Fig. 1, the structure comprises an alternating polymeric chain layer along the c axis. The CdII ions are linked into an infinite chain by double chlorine bridges, The Cd(1)···Cd(2) and Cd(1)···Cd(1A) distances in the molecule are 3.7087 (3) and 3.8756 (4) Å, respectively.

Experimental

A solution of CdCl2 (2 mmol) in methanol (20 ml) was added to a methanol solution (20 ml) of the Schiff base ligand (2 mmol, 0.48 g). Red crystals of (I) were isolated after two weeks.

Refinement

The H atoms bonded to C and N atoms were positioned geometrically and refined using a riding model [aromatic C—H 0.93 Å, methylic C—H = 0.96 Å and N—H = 0.86 Å, Uiso(H) = 1.2 or 1.5Ueq(C, N)]. The H atoms bonded to O atoms were located in a difference Fourier maps and refined with O—H distance restraints of 0.85 (2) and Uiso(H) = 1.5Ueq(O).

Figures

Fig. 1.
The structure of title compound, with displacement ellipsoids for non-H atoms drawn at the 50% probability level.

Crystal data

[Cd3Cl6(C15H15NO2)2(CH4O)2]F(000) = 2152
Mr = 1096.57Dx = 1.860 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 3942 reflections
a = 19.7697 (5) Åθ = 1.8–25.0°
b = 13.9554 (3) ŵ = 2.07 mm1
c = 15.1449 (4) ÅT = 296 K
β = 110.423 (1)°Block, red
V = 3915.74 (17) Å30.15 × 0.13 × 0.05 mm
Z = 4

Data collection

Bruker APEXII diffractometer3350 independent reflections
Radiation source: fine-focus sealed tube2773 reflections with I > 2σ(I)
graphiteRint = 0.033
ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −23→23
Tmin = 0.736, Tmax = 0.898k = −16→16
13592 measured reflectionsl = −15→18

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.026Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.060H atoms treated by a mixture of independent and constrained refinement
S = 1.05w = 1/[σ2(Fo2) + (0.0247P)2 + 2.9063P] where P = (Fo2 + 2Fc2)/3
3350 reflections(Δ/σ)max = 0.002
226 parametersΔρmax = 0.36 e Å3
1 restraintΔρmin = −0.34 e Å3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Cd10.542829 (14)1.284415 (15)−0.113758 (18)0.04061 (9)
Cd20.50001.50000.00000.04260 (11)
N10.46501 (15)0.97593 (18)−0.16754 (19)0.0373 (6)
H1D0.47101.0367−0.17040.045*
O10.53998 (12)1.12806 (14)−0.10453 (16)0.0440 (6)
O20.65586 (13)1.21264 (15)0.01463 (18)0.0502 (6)
O30.41084 (17)1.48567 (18)−0.1495 (2)0.0734 (9)
H3C0.406 (3)1.431 (2)−0.174 (3)0.110*
Cl10.59671 (6)1.44929 (6)−0.07253 (8)0.0632 (3)
Cl20.48990 (5)1.31686 (6)0.02126 (6)0.0447 (2)
Cl30.41178 (5)1.27831 (6)−0.24124 (6)0.0449 (2)
C10.2053 (2)0.8336 (3)−0.4388 (3)0.0702 (12)
H1A0.20540.7648−0.43960.105*
H1B0.19950.8574−0.50050.105*
H1C0.16610.8558−0.42060.105*
C20.27528 (19)0.8692 (2)−0.3696 (3)0.0470 (9)
C30.3294 (2)0.8076 (2)−0.3173 (3)0.0534 (10)
H3A0.32280.7420−0.32720.064*
C40.3923 (2)0.8400 (2)−0.2515 (3)0.0487 (9)
H4A0.42780.7968−0.21770.058*
C50.40256 (18)0.9373 (2)−0.2360 (2)0.0361 (8)
C60.3509 (2)1.0007 (2)−0.2894 (3)0.0433 (8)
H6A0.35861.0664−0.28140.052*
C70.28796 (19)0.9666 (2)−0.3544 (3)0.0469 (9)
H7A0.25301.0098−0.38910.056*
C80.51477 (18)0.9305 (2)−0.1005 (2)0.0373 (8)
H8A0.50950.8648−0.09470.045*
C90.57599 (18)0.9754 (2)−0.0364 (2)0.0356 (8)
C100.6274 (2)0.9190 (2)0.0325 (3)0.0498 (9)
H10A0.61960.85370.03650.060*
C110.6876 (2)0.9600 (3)0.0925 (3)0.0557 (10)
H11A0.72180.92220.13670.067*
C120.6997 (2)1.0591 (3)0.0893 (3)0.0510 (9)
H12A0.74141.08630.13150.061*
C130.65035 (18)1.1156 (2)0.0245 (2)0.0398 (8)
C140.58669 (17)1.0755 (2)−0.0415 (2)0.0344 (7)
C150.7108 (2)1.2622 (3)0.0885 (3)0.0693 (12)
H15A0.74601.21700.12520.104*
H15B0.68931.29420.12820.104*
H15C0.73381.30840.06140.104*
C160.3865 (3)1.5562 (4)−0.2154 (3)0.110 (2)
H16A0.34951.5309−0.27010.165*
H16B0.42571.5796−0.23290.165*
H16C0.36701.6078−0.18970.165*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cd10.04572 (18)0.02655 (13)0.04443 (16)−0.00188 (10)0.00927 (13)−0.00170 (10)
Cd20.0499 (3)0.02725 (18)0.0422 (2)0.00221 (15)0.00547 (19)−0.00150 (14)
N10.0407 (18)0.0263 (13)0.0430 (17)−0.0029 (12)0.0120 (15)−0.0001 (12)
O10.0432 (15)0.0273 (11)0.0472 (14)0.0025 (10)−0.0022 (12)0.0032 (10)
O20.0454 (16)0.0383 (13)0.0571 (16)−0.0100 (11)0.0055 (13)−0.0043 (11)
O30.086 (2)0.0433 (16)0.0607 (19)0.0093 (15)−0.0132 (17)−0.0099 (14)
Cl10.0737 (7)0.0389 (5)0.0889 (8)−0.0198 (5)0.0433 (6)−0.0183 (5)
Cl20.0541 (6)0.0300 (4)0.0472 (5)−0.0023 (4)0.0141 (5)0.0016 (4)
Cl30.0422 (5)0.0437 (5)0.0436 (5)−0.0017 (4)0.0085 (4)−0.0031 (4)
C10.044 (3)0.060 (3)0.087 (3)−0.001 (2)−0.002 (2)−0.008 (2)
C20.039 (2)0.045 (2)0.053 (2)−0.0029 (17)0.0115 (19)−0.0053 (17)
C30.054 (3)0.0310 (18)0.065 (3)−0.0059 (17)0.009 (2)−0.0031 (17)
C40.047 (2)0.0344 (19)0.052 (2)0.0025 (16)0.002 (2)0.0024 (16)
C50.036 (2)0.0332 (17)0.0384 (19)−0.0032 (14)0.0118 (17)−0.0014 (14)
C60.048 (2)0.0312 (17)0.048 (2)−0.0007 (16)0.0138 (19)0.0014 (15)
C70.038 (2)0.0418 (19)0.052 (2)0.0071 (16)0.005 (2)0.0014 (17)
C80.043 (2)0.0285 (16)0.039 (2)0.0009 (15)0.0134 (18)0.0027 (14)
C90.038 (2)0.0323 (16)0.0347 (19)0.0039 (14)0.0108 (17)0.0013 (14)
C100.059 (3)0.0365 (19)0.047 (2)0.0086 (18)0.009 (2)0.0056 (16)
C110.055 (3)0.048 (2)0.048 (2)0.0139 (19)−0.002 (2)0.0068 (18)
C120.040 (2)0.058 (2)0.044 (2)0.0038 (18)0.0008 (19)−0.0074 (18)
C130.040 (2)0.0357 (18)0.040 (2)−0.0002 (15)0.0102 (18)−0.0027 (15)
C140.037 (2)0.0319 (17)0.0341 (18)0.0030 (14)0.0121 (17)−0.0015 (14)
C150.069 (3)0.059 (2)0.066 (3)−0.026 (2)0.005 (2)−0.016 (2)
C160.148 (6)0.076 (3)0.062 (3)0.018 (3)−0.018 (3)−0.001 (3)

Geometric parameters (Å, °)

Cd1—O12.188 (2)C2—C71.387 (5)
Cd1—Cl12.5208 (9)C3—C41.371 (5)
Cd1—O22.597 (2)C3—H3A0.9300
Cd1—Cl32.6374 (9)C4—C51.382 (4)
Cd1—Cl22.6410 (9)C4—H4A0.9300
Cd1—Cl3i2.6476 (9)C5—C61.380 (4)
Cd2—O3ii2.343 (3)C6—C71.375 (5)
Cd2—O32.343 (3)C6—H6A0.9300
Cd2—Cl22.5924 (8)C7—H7A0.9300
Cd2—Cl2ii2.5924 (8)C8—C91.407 (4)
Cd2—Cl12.6133 (10)C8—H8A0.9300
Cd2—Cl1ii2.6133 (10)C9—C101.414 (4)
N1—C81.306 (4)C9—C141.418 (4)
N1—C51.413 (4)C10—C111.348 (5)
N1—H1D0.8600C10—H10A0.9300
O1—C141.299 (4)C11—C121.408 (5)
O2—C131.372 (4)C11—H11A0.9300
O2—C151.435 (4)C12—C131.366 (5)
O3—C161.365 (5)C12—H12A0.9300
O3—H3C0.838 (19)C13—C141.421 (4)
Cl3—Cd1i2.6476 (9)C15—H15A0.9600
C1—C21.499 (5)C15—H15B0.9600
C1—H1A0.9600C15—H15C0.9600
C1—H1B0.9600C16—H16A0.9600
C1—H1C0.9600C16—H16B0.9600
C2—C31.385 (5)C16—H16C0.9600
O1—Cd1—Cl1155.83 (6)C3—C2—C1122.3 (3)
O1—Cd1—O266.56 (7)C7—C2—C1120.7 (3)
Cl1—Cd1—O289.30 (5)C4—C3—C2122.4 (3)
O1—Cd1—Cl388.51 (6)C4—C3—H3A118.8
Cl1—Cd1—Cl3115.66 (3)C2—C3—H3A118.8
O2—Cd1—Cl3154.74 (5)C3—C4—C5119.3 (3)
O1—Cd1—Cl295.48 (6)C3—C4—H4A120.3
Cl1—Cd1—Cl284.21 (3)C5—C4—H4A120.3
O2—Cd1—Cl287.50 (6)C6—C5—C4119.7 (3)
Cl3—Cd1—Cl291.09 (3)C6—C5—N1117.7 (3)
O1—Cd1—Cl3i92.56 (6)C4—C5—N1122.6 (3)
Cl1—Cd1—Cl3i89.92 (3)C7—C6—C5119.8 (3)
O2—Cd1—Cl3i99.00 (6)C7—C6—H6A120.1
Cl3—Cd1—Cl3i85.55 (3)C5—C6—H6A120.1
Cl2—Cd1—Cl3i171.21 (3)C6—C7—C2121.7 (3)
O3ii—Cd2—O3180.00 (12)C6—C7—H7A119.2
O3ii—Cd2—Cl291.64 (7)C2—C7—H7A119.2
O3—Cd2—Cl288.36 (7)N1—C8—C9123.6 (3)
O3ii—Cd2—Cl2ii88.36 (7)N1—C8—H8A118.2
O3—Cd2—Cl2ii91.64 (7)C9—C8—H8A118.2
Cl2—Cd2—Cl2ii180.000 (1)C8—C9—C10119.0 (3)
O3ii—Cd2—Cl190.88 (9)C8—C9—C14120.7 (3)
O3—Cd2—Cl189.12 (9)C10—C9—C14120.4 (3)
Cl2—Cd2—Cl183.37 (3)C11—C10—C9120.0 (3)
Cl2ii—Cd2—Cl196.63 (3)C11—C10—H10A120.0
O3ii—Cd2—Cl1ii89.12 (9)C9—C10—H10A120.0
O3—Cd2—Cl1ii90.88 (9)C10—C11—C12120.9 (3)
Cl2—Cd2—Cl1ii96.63 (3)C10—C11—H11A119.5
Cl2ii—Cd2—Cl1ii83.37 (3)C12—C11—H11A119.5
Cl1—Cd2—Cl1ii180.000 (1)C13—C12—C11120.3 (3)
C8—N1—C5127.9 (3)C13—C12—H12A119.9
C8—N1—H1D116.1C11—C12—H12A119.9
C5—N1—H1D116.1C12—C13—O2125.7 (3)
C14—O1—Cd1125.63 (19)C12—C13—C14120.9 (3)
C13—O2—C15117.3 (3)O2—C13—C14113.4 (3)
C13—O2—Cd1112.48 (19)O1—C14—C9121.0 (3)
C15—O2—Cd1128.1 (2)O1—C14—C13121.5 (3)
C16—O3—Cd2126.9 (3)C9—C14—C13117.5 (3)
C16—O3—H3C112 (4)O2—C15—H15A109.5
Cd2—O3—H3C116 (4)O2—C15—H15B109.5
Cd1—Cl1—Cd292.48 (3)H15A—C15—H15B109.5
Cd2—Cl2—Cd190.25 (3)O2—C15—H15C109.5
Cd1—Cl3—Cd1i94.33 (3)H15A—C15—H15C109.5
C2—C1—H1A109.5H15B—C15—H15C109.5
C2—C1—H1B109.5O3—C16—H16A109.5
H1A—C1—H1B109.5O3—C16—H16B109.5
C2—C1—H1C109.5H16A—C16—H16B109.5
H1A—C1—H1C109.5O3—C16—H16C109.5
H1B—C1—H1C109.5H16A—C16—H16C109.5
C3—C2—C7117.0 (3)H16B—C16—H16C109.5
Cl1—Cd1—O1—C149.2 (3)Cl2—Cd1—Cl3—Cd1i168.17 (2)
O2—Cd1—O1—C146.0 (2)Cl3i—Cd1—Cl3—Cd1i−3.70 (4)
Cl3—Cd1—O1—C14−169.9 (2)C7—C2—C3—C41.6 (6)
Cl2—Cd1—O1—C14−78.9 (2)C1—C2—C3—C4−177.5 (4)
Cl3i—Cd1—O1—C14104.7 (2)C2—C3—C4—C50.3 (6)
O1—Cd1—O2—C13−5.0 (2)C3—C4—C5—C6−2.7 (5)
Cl1—Cd1—O2—C13176.3 (2)C3—C4—C5—N1178.1 (3)
Cl3—Cd1—O2—C134.8 (3)C8—N1—C5—C6168.6 (3)
Cl2—Cd1—O2—C1392.1 (2)C8—N1—C5—C4−12.3 (5)
Cl3i—Cd1—O2—C13−93.9 (2)C4—C5—C6—C73.3 (5)
O1—Cd1—O2—C15−167.6 (3)N1—C5—C6—C7−177.6 (3)
Cl1—Cd1—O2—C1513.8 (3)C5—C6—C7—C2−1.4 (5)
Cl3—Cd1—O2—C15−157.7 (3)C3—C2—C7—C6−1.0 (5)
Cl2—Cd1—O2—C15−70.5 (3)C1—C2—C7—C6178.1 (4)
Cl3i—Cd1—O2—C15103.6 (3)C5—N1—C8—C9178.9 (3)
Cl2—Cd2—O3—C16−174.9 (4)N1—C8—C9—C10−178.8 (3)
Cl2ii—Cd2—O3—C165.1 (4)N1—C8—C9—C140.3 (5)
Cl1—Cd2—O3—C16−91.5 (4)C8—C9—C10—C11177.7 (3)
Cl1ii—Cd2—O3—C1688.5 (4)C14—C9—C10—C11−1.4 (5)
O1—Cd1—Cl1—Cd2−113.74 (16)C9—C10—C11—C121.6 (6)
O2—Cd1—Cl1—Cd2−110.81 (6)C10—C11—C12—C13−0.4 (6)
Cl3—Cd1—Cl1—Cd265.17 (4)C11—C12—C13—O2179.8 (3)
Cl2—Cd1—Cl1—Cd2−23.25 (3)C11—C12—C13—C14−0.9 (5)
Cl3i—Cd1—Cl1—Cd2150.19 (3)C15—O2—C13—C12−12.1 (5)
O3ii—Cd2—Cl1—Cd1115.31 (7)Cd1—O2—C13—C12−176.7 (3)
O3—Cd2—Cl1—Cd1−64.69 (7)C15—O2—C13—C14168.6 (3)
Cl2—Cd2—Cl1—Cd123.75 (3)Cd1—O2—C13—C144.0 (3)
Cl2ii—Cd2—Cl1—Cd1−156.25 (3)Cd1—O1—C14—C9173.8 (2)
O3ii—Cd2—Cl2—Cd1−113.28 (9)Cd1—O1—C14—C13−6.4 (4)
O3—Cd2—Cl2—Cd166.72 (9)C8—C9—C14—O10.8 (5)
Cl1—Cd2—Cl2—Cd1−22.59 (3)C10—C9—C14—O1179.9 (3)
Cl1ii—Cd2—Cl2—Cd1157.41 (3)C8—C9—C14—C13−178.9 (3)
O1—Cd1—Cl2—Cd2179.14 (6)C10—C9—C14—C130.1 (5)
Cl1—Cd1—Cl2—Cd223.43 (3)C12—C13—C14—O1−178.8 (3)
O2—Cd1—Cl2—Cd2112.98 (5)O2—C13—C14—O10.6 (4)
O1—Cd1—Cl3—Cd1i−96.38 (6)C12—C13—C14—C91.0 (5)
Cl1—Cd1—Cl3—Cd1i84.07 (3)O2—C13—C14—C9−179.6 (3)
O2—Cd1—Cl3—Cd1i−105.40 (14)

Symmetry codes: (i) −x+1, y, −z−1/2; (ii) −x+1, −y+3, −z.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1D···O10.861.882.574 (3)137
O3—H3C···Cl30.84 (2)2.38 (2)3.213 (3)170 (5)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2645).

References

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