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Acta Crystallogr Sect E Struct Rep Online. 2008 May 1; 64(Pt 5): m714–m715.
Published online 2008 April 26. doi:  10.1107/S1600536808011331
PMCID: PMC2961263

Aqua­bis(1H-imidazole-κN 3)bis­(4-methyl­benzoato-κ2 O,O′)cadmium(II)

Abstract

In the title compound, [Cd(C8H7O2)2(C3H4N2)2(H2O)], the CdII atom is coordinated by four carboxyl­ate O atoms from two bidentate chelating 4-methyl­benzoate ligands, two N atoms from two imidazole ligands and one water mol­ecule in a distorted penta­gonal bipyramidal geometry. Inter­molecular O—H(...)O hydrogen bonds between the coordinated water mol­ecule and the carboxyl­ate O atoms of 4-methyl­benzoate lead to an infinite chain. These chains are further self-assembled into a two-dimensional layer through N—H(...)O hydrogen bonds between the imidazole ligands and carboxyl­ate groups. One of the imidazole ligands is disordered over two positions with site-occupancy factors of 0.737 (4) and 0.263 (4).

Related literature

For related literature, see: Song et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0m714-scheme1.jpg

Experimental

Crystal data

  • [Cd(C8H7O2)2(C3H4N2)2(H2O)]
  • M r = 536.85
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m714-efi1.jpg
  • a = 6.1355 (1) Å
  • b = 12.4338 (3) Å
  • c = 15.4771 (3) Å
  • α = 91.396 (1)°
  • β = 97.765 (1)°
  • γ = 98.304 (1)°
  • V = 1156.46 (4) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.98 mm−1
  • T = 296 (2) K
  • 0.26 × 0.23 × 0.20 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.784, T max = 0.828
  • 14653 measured reflections
  • 4764 independent reflections
  • 4515 reflections with I > 2σ(I)
  • R int = 0.037

Refinement

  • R[F 2 > 2σ(F 2)] = 0.023
  • wR(F 2) = 0.059
  • S = 1.08
  • 4764 reflections
  • 314 parameters
  • 37 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.27 e Å−3
  • Δρmin = −0.46 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [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: SHELXTL.

Table 1
Selected geometric parameters (Å, °)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808011331/hy2128sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808011331/hy2128Isup2.hkl

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

Acknowledgments

The authors acknowledge Guangdong Ocean University for supporting this work.

supplementary crystallographic information

Comment

In the structural investigation of 4-methylbenzoate complexes, it has been found that the 4-methylbenzoate functions as bidentate and monodentate ligands (Song et al., 2007). In this paper, we report the crystal structure of the title compound, a new Cd complex obtained by the reaction of 4-methylbenzoic acid, imidazole and cadmium chloride in alkaline aqueous solution.

As illustrated in Fig. 1, the CdII atom exists in a distorted pentagonal bipyramidal geometry, defined by four carboxylate O atoms from two bidentate chelating 4-methylbenzoate ligands, two N atoms from two imidazole ligands and one water molecule (Table 1). One of the imidazole ligands is disordered over two positions with site occupancy factors of 0.737 (4) and 0.263 (4). Intermolecular O—H···O hydrogen bonds (Table 2) lead to infinite chains, involving the coordinated water molecules as donors and the O atoms of 4-methylbenzoate ligands as acceptors. These chains are further self-assembled into a two-dimensional supramolecular network through intermolecular N—H···O hydrogen bonds between the imidazole ligands and carboxylate groups (Fig. 2).

Experimental

A mixture of cadmium chloride (0.183 g, 1 mmol), 4-methylbenzoic acid (0.136 g, 1 mmol), imidazole (0.068 g, 1 mmol), NaOH (0.06 g, 1.5 mmol) and H2O (12 ml) was sealed in a 23 ml Teflon-lined reactor, which was heated at 433 K for 3 d and then cooled to room temperature at a rate of 10 K h-1. The crystals obtained were washed with water and dried in air.

Refinement

H atoms attached to C and N atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 (aromatic) and 0.96 (methyl) Å and N—H = 0.86 Å and with Uiso(H) = 1.2Ueq(C,N). H atoms of the water molecule were located in a difference Fourier map and refined with restraints of O—H = 0.82 (1) Å and H···H= 1.34 (2) Å and with Uiso(H) = 1.5Ueq(O). Site occupancy factors of the disordered imidazole ligand were refined.

Figures

Fig. 1.
The molecular structure of the title compound. Displacement ellipsoids are drawn as the 30% probability level. H atoms have been omitted for clarity.
Fig. 2.
A view of the two-dimensional layer in the title compound.

Crystal data

[Cd(C8H7O2)2(C3H4N2)2(H2O)]Z = 2
Mr = 536.85F000 = 544
Triclinic, P1Dx = 1.542 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 6.1355 (1) ÅCell parameters from 3600 reflections
b = 12.4338 (3) Åθ = 1.4–28º
c = 15.4771 (3) ŵ = 0.98 mm1
α = 91.396 (1)ºT = 296 (2) K
β = 97.765 (1)ºBlock, colorless
γ = 98.304 (1)º0.26 × 0.23 × 0.20 mm
V = 1156.46 (4) Å3

Data collection

Bruker SMART APEXII CCD area-detector diffractometer4764 independent reflections
Radiation source: fine-focus sealed tube4515 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.037
T = 296(2) Kθmax = 26.5º
[var phi] and ω scansθmin = 1.3º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −7→7
Tmin = 0.784, Tmax = 0.828k = −15→15
14653 measured reflectionsl = −18→19

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.023H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.059  w = 1/[σ2(Fo2) + (0.0265P)2 + 0.2332P] where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.010
4764 reflectionsΔρmax = 0.27 e Å3
314 parametersΔρmin = −0.46 e Å3
37 restraintsExtinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0610 (16)

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

xyzUiso*/UeqOcc. (<1)
C10.9109 (3)0.68747 (15)0.20150 (12)0.0325 (4)
C21.0359 (3)0.79413 (16)0.18052 (12)0.0360 (4)
C31.2641 (4)0.81996 (19)0.20736 (15)0.0462 (5)
H31.34050.77050.23830.055*
C41.3774 (5)0.9190 (2)0.18814 (17)0.0616 (7)
H41.52960.93540.20650.074*
C51.2686 (6)0.9941 (2)0.14216 (18)0.0694 (9)
C61.0429 (6)0.9680 (2)0.11549 (17)0.0636 (7)
H60.96711.01770.08440.076*
C70.9270 (4)0.86914 (19)0.13418 (15)0.0483 (5)
H70.77490.85310.11540.058*
C81.3923 (9)1.1036 (3)0.1231 (3)0.1242 (18)
H8A1.46161.09640.07170.186*
H8B1.50411.12890.17170.186*
H8C1.28951.15490.11390.186*
C90.7907 (3)0.29695 (15)0.32072 (12)0.0339 (4)
C100.8303 (3)0.18454 (15)0.34383 (12)0.0327 (4)
C111.0249 (3)0.14673 (16)0.33053 (14)0.0393 (4)
H111.13660.19250.30890.047*
C121.0542 (4)0.04120 (17)0.34930 (15)0.0422 (5)
H121.18430.01650.33840.051*
C130.8944 (4)−0.02866 (16)0.38390 (13)0.0388 (4)
C140.7012 (4)0.01078 (17)0.39875 (15)0.0460 (5)
H140.5927−0.03380.42320.055*
C150.6680 (4)0.11496 (17)0.37780 (15)0.0429 (5)
H150.53550.13890.38650.052*
C160.9287 (5)−0.14287 (18)0.40544 (17)0.0559 (6)
H16A1.0697−0.15600.39050.084*
H16B0.8119−0.19350.37280.084*
H16C0.9265−0.15190.46670.084*
C200.4871 (4)0.61585 (18)0.41076 (14)0.0424 (5)
H200.35090.62070.37770.051*
C210.5421 (4)0.64415 (19)0.49653 (15)0.0517 (6)
H210.45210.67090.53320.062*
C220.8214 (4)0.58717 (17)0.44726 (13)0.0396 (4)
H220.96190.56840.44510.047*
Cd10.68370 (2)0.491827 (10)0.250662 (8)0.02905 (7)
N10.6629 (3)0.57885 (13)0.38005 (10)0.0330 (3)
N20.7550 (4)0.62584 (15)0.51870 (12)0.0487 (5)
H20.83260.63720.56950.058*
O11.0144 (2)0.62012 (12)0.24245 (10)0.0424 (3)
O20.7032 (2)0.66821 (12)0.17868 (10)0.0408 (3)
O30.9568 (3)0.36908 (11)0.31565 (10)0.0420 (3)
O40.5945 (3)0.31678 (12)0.30732 (11)0.0468 (4)
O1W0.2938 (2)0.47353 (12)0.22005 (10)0.0395 (3)
H1W0.221 (4)0.4298 (14)0.2482 (15)0.059*
H2W0.228 (4)0.5262 (13)0.2184 (17)0.059*
C170.8273 (6)0.3438 (4)0.0917 (2)0.0580 (10)0.737 (4)
H170.95760.33150.12570.070*0.737 (4)
C180.7560 (6)0.3045 (4)0.0092 (2)0.0633 (11)0.737 (4)
H180.83120.2643−0.02510.076*0.737 (4)
C190.508 (3)0.3921 (12)0.0535 (6)0.0420 (16)0.737 (4)
H190.37280.41790.05380.050*0.737 (4)
N30.668 (2)0.4081 (12)0.1184 (10)0.0411 (13)0.737 (4)
N40.5551 (7)0.3347 (5)−0.0138 (5)0.0450 (11)0.737 (4)
H4A0.47190.3196−0.06320.054*0.737 (4)
C17'0.8520 (17)0.4185 (11)0.0683 (6)0.0580 (10)0.263 (4)
H17'0.99190.45710.08830.070*0.263 (4)
C18'0.7834 (18)0.3789 (12)−0.0139 (6)0.0633 (11)0.263 (4)
H18'0.87120.3675−0.05680.076*0.263 (4)
C19'0.512 (7)0.379 (4)0.0592 (19)0.0420 (16)0.263 (4)
H19'0.36900.38110.07210.050*0.263 (4)
N3'0.690 (7)0.394 (4)0.117 (3)0.0411 (13)0.263 (4)
N4'0.561 (2)0.3591 (18)−0.0207 (18)0.0450 (11)0.263 (4)
H4'0.46830.3381−0.06700.054*0.263 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0379 (10)0.0348 (10)0.0259 (9)0.0070 (8)0.0076 (8)−0.0024 (7)
C20.0439 (11)0.0367 (10)0.0281 (9)0.0036 (8)0.0108 (8)−0.0024 (8)
C30.0432 (11)0.0526 (13)0.0419 (12)0.0010 (10)0.0103 (9)−0.0041 (10)
C40.0575 (15)0.0704 (17)0.0511 (14)−0.0175 (13)0.0183 (12)−0.0110 (13)
C50.097 (2)0.0552 (15)0.0481 (15)−0.0246 (15)0.0208 (15)−0.0025 (12)
C60.095 (2)0.0448 (13)0.0475 (14)0.0013 (14)0.0059 (14)0.0121 (11)
C70.0587 (14)0.0435 (12)0.0412 (12)0.0043 (10)0.0039 (10)0.0052 (10)
C80.179 (5)0.079 (2)0.092 (3)−0.065 (3)0.025 (3)0.011 (2)
C90.0439 (11)0.0332 (10)0.0256 (9)0.0082 (8)0.0060 (8)0.0000 (7)
C100.0386 (10)0.0293 (9)0.0291 (9)0.0033 (7)0.0032 (8)−0.0003 (7)
C110.0404 (11)0.0339 (10)0.0454 (12)0.0041 (8)0.0138 (9)0.0038 (8)
C120.0431 (11)0.0362 (11)0.0506 (13)0.0127 (9)0.0113 (10)0.0007 (9)
C130.0500 (12)0.0281 (9)0.0363 (10)0.0036 (8)0.0023 (9)−0.0014 (8)
C140.0474 (12)0.0357 (11)0.0548 (13)−0.0016 (9)0.0135 (10)0.0081 (9)
C150.0363 (10)0.0381 (11)0.0554 (13)0.0048 (8)0.0108 (9)0.0032 (9)
C160.0824 (18)0.0313 (11)0.0546 (14)0.0106 (11)0.0091 (13)0.0045 (10)
C200.0400 (11)0.0468 (12)0.0405 (11)0.0038 (9)0.0100 (9)−0.0049 (9)
C210.0681 (16)0.0471 (12)0.0410 (12)−0.0028 (11)0.0259 (12)−0.0112 (10)
C220.0473 (11)0.0346 (10)0.0341 (11)0.0025 (8)−0.0010 (9)0.0037 (8)
Cd10.03054 (9)0.03191 (10)0.02451 (9)0.00588 (5)0.00252 (5)−0.00215 (5)
N10.0391 (8)0.0324 (8)0.0271 (8)0.0045 (6)0.0050 (7)−0.0009 (6)
N20.0710 (14)0.0416 (10)0.0264 (9)−0.0088 (9)0.0009 (8)−0.0006 (7)
O10.0410 (8)0.0393 (8)0.0496 (9)0.0120 (6)0.0089 (7)0.0074 (6)
O20.0381 (8)0.0463 (8)0.0358 (8)0.0026 (6)0.0008 (6)0.0045 (6)
O30.0522 (9)0.0313 (7)0.0417 (8)0.0018 (6)0.0085 (7)0.0054 (6)
O40.0481 (9)0.0409 (8)0.0545 (10)0.0159 (7)0.0080 (7)0.0059 (7)
O1W0.0303 (7)0.0441 (8)0.0447 (8)0.0086 (6)0.0041 (6)0.0038 (7)
C170.0427 (15)0.089 (3)0.0413 (17)0.0138 (19)0.0016 (13)−0.0240 (18)
C180.0542 (18)0.092 (3)0.0433 (18)0.013 (2)0.0090 (14)−0.0268 (19)
C190.0507 (14)0.040 (4)0.0335 (17)0.008 (2)−0.0013 (14)0.001 (2)
N30.040 (3)0.053 (4)0.0312 (11)0.0127 (18)0.0034 (19)−0.013 (2)
N40.0624 (13)0.041 (3)0.0262 (17)−0.0024 (13)−0.0035 (9)−0.002 (2)
C17'0.0427 (15)0.089 (3)0.0413 (17)0.0138 (19)0.0016 (13)−0.0240 (18)
C18'0.0542 (18)0.092 (3)0.0433 (18)0.013 (2)0.0090 (14)−0.0268 (19)
C19'0.0507 (14)0.040 (4)0.0335 (17)0.008 (2)−0.0013 (14)0.001 (2)
N3'0.040 (3)0.053 (4)0.0312 (11)0.0127 (18)0.0034 (19)−0.013 (2)
N4'0.0624 (13)0.041 (3)0.0262 (17)−0.0024 (13)−0.0035 (9)−0.002 (2)

Geometric parameters (Å, °)

C1—O11.256 (2)C20—N11.369 (3)
C1—O21.262 (3)C20—H200.9300
C1—C21.499 (3)C21—N21.358 (3)
C2—C71.383 (3)C21—H210.9300
C2—C31.393 (3)C22—N11.315 (3)
C3—C41.384 (3)C22—N21.331 (3)
C3—H30.9300C22—H220.9300
C4—C51.381 (5)Cd1—N32.257 (13)
C4—H40.9300Cd1—N12.2805 (15)
C5—C61.379 (5)Cd1—O1W2.3514 (13)
C5—C81.516 (4)Cd1—O42.3842 (16)
C6—C71.386 (3)Cd1—O12.4128 (14)
C6—H60.9300Cd1—O22.4788 (15)
C7—H70.9300Cd1—O32.5507 (16)
C8—H8A0.9600N2—H20.8600
C8—H8B0.9600O1W—H1W0.82 (2)
C8—H8C0.9600O1W—H2W0.82 (2)
C9—O41.254 (3)C17—C181.347 (4)
C9—O31.269 (2)C17—N31.444 (10)
C9—C101.496 (3)C17—H170.9300
C10—C111.383 (3)C18—N41.345 (5)
C10—C151.390 (3)C18—H180.9300
C11—C121.382 (3)C19—N31.298 (4)
C11—H110.9300C19—N41.337 (6)
C12—C131.386 (3)C19—H190.9300
C12—H120.9300N4—H4A0.8600
C13—C141.391 (3)C17'—N3'1.33 (5)
C13—C161.504 (3)C17'—C18'1.343 (8)
C14—C151.380 (3)C17'—H17'0.9300
C14—H140.9300C18'—N4'1.343 (9)
C15—H150.9300C18'—H18'0.9300
C16—H16A0.9600C19'—N3'1.300 (9)
C16—H16B0.9600C19'—N4'1.337 (10)
C16—H16C0.9600C19'—H19'0.9300
C20—C211.350 (3)N4'—H4'0.8600
O1—C1—O2121.53 (18)N3—Cd1—O196.7 (5)
O1—C1—C2119.37 (18)N1—Cd1—O186.88 (5)
O2—C1—C2119.09 (18)O1W—Cd1—O1141.36 (5)
C7—C2—C3118.6 (2)O4—Cd1—O1137.19 (5)
C7—C2—C1120.66 (19)N3—Cd1—O288.6 (4)
C3—C2—C1120.8 (2)N1—Cd1—O289.81 (5)
C4—C3—C2120.2 (2)O1W—Cd1—O288.32 (5)
C4—C3—H3119.9O4—Cd1—O2169.31 (5)
C2—C3—H3119.9O1—Cd1—O253.35 (5)
C5—C4—C3121.2 (3)N3—Cd1—O389.8 (3)
C5—C4—H4119.4N1—Cd1—O395.21 (5)
C3—C4—H4119.4O1W—Cd1—O3134.30 (5)
C6—C5—C4118.4 (2)O4—Cd1—O353.05 (5)
C6—C5—C8120.6 (4)O1—Cd1—O384.34 (5)
C4—C5—C8121.0 (3)O2—Cd1—O3137.09 (4)
C5—C6—C7121.1 (3)C22—N1—C20105.43 (17)
C5—C6—H6119.4C22—N1—Cd1123.23 (14)
C7—C6—H6119.4C20—N1—Cd1130.55 (14)
C2—C7—C6120.5 (2)C22—N2—C21107.39 (19)
C2—C7—H7119.8C22—N2—H2126.3
C6—C7—H7119.8C21—N2—H2126.3
O4—C9—O3122.22 (19)C1—O1—Cd194.15 (12)
O4—C9—C10118.90 (18)C1—O2—Cd190.92 (12)
O3—C9—C10118.88 (18)C9—O3—Cd187.86 (12)
C11—C10—C15118.59 (18)C9—O4—Cd195.91 (13)
C11—C10—C9121.38 (17)Cd1—O1W—H1W117.5 (18)
C15—C10—C9120.02 (18)Cd1—O1W—H2W121.9 (18)
C10—C11—C12120.31 (18)H1W—O1W—H2W103.8 (15)
C10—C11—H11119.8C18—C17—N3108.7 (6)
C12—C11—H11119.8C18—C17—H17125.6
C11—C12—C13121.63 (19)N3—C17—H17125.6
C11—C12—H12119.2C17—C18—N4106.7 (5)
C13—C12—H12119.2C17—C18—H18126.6
C12—C13—C14117.65 (19)N4—C18—H18126.6
C12—C13—C16121.4 (2)N3—C19—N4113.3 (12)
C14—C13—C16121.0 (2)N3—C19—H19123.3
C15—C14—C13121.05 (19)N4—C19—H19123.3
C15—C14—H14119.5C19—N3—C17102.8 (11)
C13—C14—H14119.5C19—N3—Cd1130.1 (8)
C14—C15—C10120.7 (2)C17—N3—Cd1126.5 (8)
C14—C15—H15119.6C19—N4—C18108.0 (9)
C10—C15—H15119.6C19—N4—H4A126.0
C21—C20—N1109.4 (2)C18—N4—H4A126.0
C21—C20—H20125.3N3'—C17'—C18'110 (2)
N1—C20—H20125.3N3'—C17'—H17'125.1
C20—C21—N2106.33 (19)C18'—C17'—H17'125.1
C20—C21—H21126.8C17'—C18'—N4'105.1 (14)
N2—C21—H21126.8C17'—C18'—H18'127.5
N1—C22—N2111.4 (2)N4'—C18'—H18'127.5
N1—C22—H22124.3N3'—C19'—N4'111 (4)
N2—C22—H22124.3N3'—C19'—H19'124.3
N3—Cd1—N1174.2 (3)N4'—C19'—H19'124.3
N3—Cd1—O1W85.9 (3)C19'—N3'—C17'103 (4)
N1—Cd1—O1W88.49 (6)C19'—N4'—C18'106 (3)
N3—Cd1—O488.0 (5)C19'—N4'—H4'127.1
N1—Cd1—O492.50 (6)C18'—N4'—H4'127.1
O1W—Cd1—O481.32 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1W—H1W···O3i0.82 (2)2.104 (14)2.881 (2)157 (2)
O1W—H2W···O1i0.82 (2)1.943 (13)2.723 (2)160 (2)
N2—H2···O3ii0.862.062.905 (3)167
N4—H4A···O2iii0.861.982.813 (8)163

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2128).

References

  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Song, W.-D., Gu, C.-S., Hao, X.-M. & Liu, J.-W. (2007). Acta Cryst. E63, m1023–m1024.

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