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Acta Crystallogr Sect E Struct Rep Online. 2009 June 1; 65(Pt 6): m613.
Published online 2009 May 7. doi:  10.1107/S1600536809015943
PMCID: PMC2969561

Bis{μ-1,3-bis­[(benzimidazol-1-yl)meth­yl]benzene-κ2 N 3:N 3′}bis­[dichloridozinc(II)] dimethyl­formamide disolvate

Abstract

In the title compound, [Zn2Cl4(C22H18N4)2]·2C3H7NO, the 1,3-bis­[(benzimidazol-1-yl)meth­yl]benzene ligand bridges two ZnCl2 units, forming a centrosymmetric dinuclear mol­ecule. The ZnII atom shows a distorted tetra­hedral coordination within a Cl2N2 donor set.

Related literature

For the crystal structure of 1,3-bis­((benzimidazol-1-yl)meth­yl)benzene, which was isolated as the malonic acid co-crystal, see: Aakeröy et al. (2005 [triangle]). For related metal complexes, see: Fan et al. (2006 [triangle]); Raehm et al. (2003 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0m613-scheme1.jpg

Experimental

Crystal data

  • [Zn2Cl4(C22H18N4)2]·2C3H7NO
  • M r = 1095.54
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m613-efi1.jpg
  • a = 24.0069 (5) Å
  • b = 9.8217 (2) Å
  • c = 23.9723 (5) Å
  • β = 117.695 (1)°
  • V = 5004.8 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.22 mm−1
  • T = 120 K
  • 0.30 × 0.20 × 0.10 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan SADABS (Sheldrick, 1996 [triangle]) T min = 0.711, T max = 0.888
  • 17166 measured reflections
  • 5730 independent reflections
  • 4449 reflections with I > 2σ(I)
  • R int = 0.034

Refinement

  • R[F 2 > 2σ(F 2)] = 0.037
  • wR(F 2) = 0.097
  • S = 1.04
  • 5730 reflections
  • 309 parameters
  • H-atom parameters constrained
  • Δρmax = 0.92 e Å−3
  • Δρmin = −0.57 e Å−3

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [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: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809015943/tk2441sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809015943/tk2441Isup2.hkl

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

Acknowledgments

We acknowledge support from the Scientific Research Projects of Higher Education of Inner Mongolia (NJzy08217) and the University of Malaya.

supplementary crystallographic information

Experimental

The compound was prepared from a mixture of boric acid (0.17 g), zinc chloride (0.27 g), 1,3-bis((benzimidazol-1-yl)methyl)benzene (0.45 g) in DMF (3.6 ml) and water (0.2 ml). The mixture was sealed in 25-ml Teflon-lined stainless-steel vessel, which was heated at 423 K for 5 days. The vessel was then cooled to room temperature slowly. Crystals were picked out manually.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.99 Å) and were included in the refinement in the riding model approximation, with U(H) fixed at 1.2Ueq(C).

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of [ZnCl2(C22H18N4)]2.2DMF at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. Only one DMF molecule is shown. Unlabelled non-H atoms are related by a centre of inversion.

Crystal data

[Zn2Cl4(C22H18N4)2]·2C3H7NOF(000) = 2256
Mr = 1095.54Dx = 1.454 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 4135 reflections
a = 24.0069 (5) Åθ = 2.3–27.2°
b = 9.8217 (2) ŵ = 1.22 mm1
c = 23.9723 (5) ÅT = 120 K
β = 117.695 (1)°Prism, colorless
V = 5004.8 (2) Å30.30 × 0.20 × 0.10 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer5730 independent reflections
Radiation source: fine-focus sealed tube4449 reflections with I > 2σ(I)
graphiteRint = 0.034
ω scansθmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan SADABS (Sheldrick, 1996)h = −30→31
Tmin = 0.711, Tmax = 0.888k = −12→12
17166 measured reflectionsl = −31→28

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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0452P)2 + 5.1375P] where P = (Fo2 + 2Fc2)/3
5730 reflections(Δ/σ)max = 0.001
309 parametersΔρmax = 0.92 e Å3
0 restraintsΔρmin = −0.57 e Å3

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

xyzUiso*/Ueq
Zn10.499493 (12)0.24704 (3)0.615569 (12)0.01976 (9)
Cl10.54858 (3)0.40106 (6)0.69289 (3)0.02422 (14)
Cl20.54751 (3)0.05513 (6)0.61286 (3)0.03540 (17)
O10.28873 (14)0.6931 (3)0.61655 (11)0.0738 (8)
N10.46559 (9)0.32960 (19)0.52860 (9)0.0194 (4)
N20.42352 (9)0.33960 (19)0.42428 (9)0.0183 (4)
N30.16359 (9)0.2139 (2)0.36682 (9)0.0223 (4)
N40.08242 (9)0.2789 (2)0.38075 (9)0.0224 (4)
N50.37081 (12)0.8246 (2)0.67983 (10)0.0369 (6)
C10.43461 (10)0.4540 (2)0.50863 (10)0.0185 (5)
C20.42823 (11)0.5612 (2)0.54354 (11)0.0224 (5)
H20.44640.55740.58820.027*
C30.39418 (11)0.6732 (2)0.51009 (12)0.0263 (5)
H30.38870.74790.53220.032*
C40.36741 (11)0.6791 (2)0.44394 (12)0.0260 (5)
H40.34440.75790.42270.031*
C50.37366 (11)0.5743 (2)0.40925 (11)0.0232 (5)
H50.35560.57850.36460.028*
C60.40796 (10)0.4615 (2)0.44313 (11)0.0199 (5)
C70.45751 (11)0.2659 (2)0.47682 (11)0.0202 (5)
H70.47380.17790.47660.024*
C80.40337 (11)0.2955 (2)0.35930 (11)0.0206 (5)
H8A0.42200.20540.35950.025*
H8B0.41870.36110.33820.025*
C90.33254 (11)0.2861 (2)0.32330 (11)0.0209 (5)
C100.29914 (11)0.2108 (2)0.34747 (11)0.0208 (5)
H100.32150.16140.38560.025*
C110.23407 (11)0.2072 (2)0.31670 (11)0.0222 (5)
C120.20141 (12)0.2768 (3)0.25988 (12)0.0285 (6)
H120.15670.27420.23820.034*
C130.23399 (13)0.3496 (3)0.23511 (12)0.0338 (6)
H130.21170.39590.19610.041*
C140.29951 (12)0.3554 (3)0.26713 (11)0.0291 (6)
H140.32160.40730.25030.035*
C150.19950 (12)0.1274 (2)0.34467 (12)0.0257 (5)
H15A0.17020.06330.31260.031*
H15B0.23030.07300.38050.031*
C160.10264 (11)0.1968 (2)0.35076 (11)0.0223 (5)
H160.07660.13180.32060.027*
C170.13518 (11)0.3561 (2)0.42061 (11)0.0221 (5)
C180.14072 (12)0.4591 (2)0.46287 (11)0.0251 (5)
H180.10580.48700.46860.030*
C190.19923 (12)0.5187 (3)0.49612 (12)0.0285 (6)
H190.20470.58920.52540.034*
C200.25048 (12)0.4777 (3)0.48768 (12)0.0300 (6)
H200.28990.52140.51140.036*
C210.24572 (12)0.3754 (3)0.44588 (12)0.0283 (6)
H210.28080.34740.44050.034*
C220.18653 (11)0.3158 (2)0.41212 (11)0.0227 (5)
C230.31081 (17)0.7967 (4)0.64606 (15)0.0501 (9)
H230.28190.86430.64460.060*
C240.4155 (2)0.7252 (4)0.6803 (2)0.0749 (12)
H24A0.39290.65120.65100.112*
H24B0.43960.68830.72290.112*
H24C0.44430.76880.66720.112*
C250.3954 (2)0.9448 (4)0.71704 (16)0.0667 (12)
H25A0.36051.00250.71330.100*
H25B0.42110.99490.70200.100*
H25C0.42130.91920.76120.100*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Zn10.01891 (15)0.01906 (14)0.01959 (14)0.00064 (11)0.00751 (11)0.00179 (10)
Cl10.0220 (3)0.0268 (3)0.0201 (3)−0.0046 (2)0.0067 (2)−0.0007 (2)
Cl20.0442 (4)0.0243 (3)0.0351 (3)0.0130 (3)0.0162 (3)0.0053 (3)
O10.093 (2)0.0474 (15)0.0492 (14)−0.0216 (15)0.0061 (14)−0.0035 (12)
N10.0187 (10)0.0179 (10)0.0211 (9)0.0017 (8)0.0088 (8)0.0031 (8)
N20.0178 (10)0.0180 (9)0.0194 (9)0.0005 (8)0.0089 (8)0.0005 (7)
N30.0229 (11)0.0223 (10)0.0239 (10)−0.0048 (8)0.0126 (9)−0.0058 (8)
N40.0228 (10)0.0218 (10)0.0236 (10)−0.0057 (8)0.0116 (9)−0.0045 (8)
N50.0455 (15)0.0325 (13)0.0262 (11)−0.0073 (11)0.0112 (11)−0.0024 (10)
C10.0144 (11)0.0178 (11)0.0231 (11)−0.0012 (8)0.0085 (9)0.0003 (9)
C20.0172 (12)0.0240 (12)0.0237 (12)−0.0005 (9)0.0078 (10)−0.0013 (9)
C30.0247 (13)0.0203 (12)0.0344 (13)0.0034 (10)0.0143 (11)−0.0034 (10)
C40.0224 (13)0.0211 (12)0.0328 (13)0.0068 (10)0.0116 (11)0.0061 (10)
C50.0207 (12)0.0224 (12)0.0249 (12)0.0035 (9)0.0092 (10)0.0037 (9)
C60.0160 (11)0.0202 (12)0.0238 (12)−0.0021 (9)0.0096 (9)0.0001 (9)
C70.0168 (11)0.0186 (11)0.0248 (12)0.0005 (9)0.0094 (9)0.0031 (9)
C80.0229 (12)0.0219 (11)0.0199 (11)0.0008 (9)0.0123 (10)0.0003 (9)
C90.0247 (13)0.0202 (11)0.0203 (11)−0.0013 (9)0.0128 (10)−0.0025 (9)
C100.0243 (12)0.0180 (11)0.0198 (11)0.0005 (9)0.0099 (10)−0.0002 (9)
C110.0266 (13)0.0183 (11)0.0236 (12)−0.0034 (9)0.0132 (10)−0.0067 (9)
C120.0236 (13)0.0315 (14)0.0244 (12)−0.0035 (10)0.0062 (10)−0.0048 (10)
C130.0312 (15)0.0420 (16)0.0202 (12)−0.0028 (12)0.0051 (11)0.0071 (11)
C140.0290 (14)0.0343 (14)0.0240 (12)−0.0048 (11)0.0124 (11)0.0049 (11)
C150.0268 (13)0.0235 (13)0.0307 (13)−0.0033 (10)0.0166 (11)−0.0057 (10)
C160.0218 (12)0.0229 (12)0.0227 (12)−0.0063 (9)0.0106 (10)−0.0034 (9)
C170.0220 (12)0.0212 (12)0.0210 (11)−0.0034 (9)0.0082 (10)0.0000 (9)
C180.0274 (13)0.0227 (12)0.0264 (12)−0.0009 (10)0.0135 (11)−0.0037 (10)
C190.0316 (14)0.0248 (13)0.0251 (13)−0.0028 (11)0.0100 (11)−0.0058 (10)
C200.0250 (13)0.0295 (14)0.0311 (14)−0.0088 (11)0.0093 (11)−0.0077 (11)
C210.0235 (13)0.0293 (14)0.0323 (13)−0.0060 (10)0.0130 (11)−0.0050 (11)
C220.0256 (13)0.0206 (12)0.0225 (12)−0.0053 (10)0.0117 (10)−0.0033 (9)
C230.053 (2)0.0425 (18)0.0376 (17)−0.0103 (16)0.0071 (15)0.0080 (14)
C240.075 (3)0.078 (3)0.083 (3)0.007 (2)0.047 (3)−0.009 (2)
C250.094 (3)0.043 (2)0.0422 (19)−0.0191 (19)0.014 (2)−0.0115 (15)

Geometric parameters (Å, °)

Zn1—N12.022 (2)C8—H8B0.9900
Zn1—N4i2.025 (2)C9—C141.383 (3)
Zn1—Cl12.2544 (6)C9—C101.399 (3)
Zn1—Cl22.2262 (7)C10—C111.384 (3)
O1—C231.211 (4)C10—H100.9500
N1—C71.321 (3)C11—C121.394 (4)
N1—C11.394 (3)C11—C151.506 (3)
N2—C71.349 (3)C12—C131.381 (4)
N2—C61.391 (3)C12—H120.9500
N2—C81.465 (3)C13—C141.394 (4)
N3—C161.339 (3)C13—H130.9500
N3—C221.389 (3)C14—H140.9500
N3—C151.474 (3)C15—H15A0.9900
N4—C161.314 (3)C15—H15B0.9900
N4—C171.403 (3)C16—H160.9500
N4—Zn1i2.025 (2)C17—C181.393 (3)
N5—C231.312 (4)C17—C221.397 (3)
N5—C251.431 (4)C18—C191.382 (3)
N5—C241.447 (5)C18—H180.9500
C1—C61.395 (3)C19—C201.396 (4)
C1—C21.397 (3)C19—H190.9500
C2—C31.382 (3)C20—C211.386 (4)
C2—H20.9500C20—H200.9500
C3—C41.408 (3)C21—C221.396 (3)
C3—H30.9500C21—H210.9500
C4—C51.375 (3)C23—H230.9500
C4—H40.9500C24—H24A0.9800
C5—C61.394 (3)C24—H24B0.9800
C5—H50.9500C24—H24C0.9800
C7—H70.9500C25—H25A0.9800
C8—C91.510 (3)C25—H25B0.9800
C8—H8A0.9900C25—H25C0.9800
N1—Zn1—N4i99.30 (8)C10—C11—C12119.4 (2)
N1—Zn1—Cl1112.62 (6)C10—C11—C15119.7 (2)
N1—Zn1—Cl2105.97 (6)C12—C11—C15120.9 (2)
N4i—Zn1—Cl1101.28 (6)C13—C12—C11120.0 (2)
N4i—Zn1—Cl2114.92 (6)C13—C12—H12120.0
Cl1—Zn1—Cl2120.81 (3)C11—C12—H12120.0
C7—N1—C1105.68 (18)C12—C13—C14120.2 (2)
C7—N1—Zn1126.28 (15)C12—C13—H13119.9
C1—N1—Zn1126.89 (15)C14—C13—H13119.9
C7—N2—C6107.21 (19)C9—C14—C13120.4 (2)
C7—N2—C8126.25 (19)C9—C14—H14119.8
C6—N2—C8126.44 (19)C13—C14—H14119.8
C16—N3—C22107.3 (2)N3—C15—C11113.3 (2)
C16—N3—C15124.6 (2)N3—C15—H15A108.9
C22—N3—C15127.7 (2)C11—C15—H15A108.9
C16—N4—C17105.0 (2)N3—C15—H15B108.9
C16—N4—Zn1i124.06 (16)C11—C15—H15B108.9
C17—N4—Zn1i128.75 (16)H15A—C15—H15B107.7
C23—N5—C25124.9 (3)N4—C16—N3113.5 (2)
C23—N5—C24117.5 (3)N4—C16—H16123.3
C25—N5—C24117.6 (3)N3—C16—H16123.3
N1—C1—C6109.0 (2)C18—C17—C22121.3 (2)
N1—C1—C2130.1 (2)C18—C17—N4129.7 (2)
C6—C1—C2120.9 (2)C22—C17—N4109.0 (2)
C3—C2—C1116.9 (2)C19—C18—C17117.1 (2)
C3—C2—H2121.6C19—C18—H18121.5
C1—C2—H2121.6C17—C18—H18121.5
C2—C3—C4121.6 (2)C18—C19—C20121.5 (2)
C2—C3—H3119.2C18—C19—H19119.3
C4—C3—H3119.2C20—C19—H19119.3
C5—C4—C3121.9 (2)C21—C20—C19122.1 (2)
C5—C4—H4119.0C21—C20—H20118.9
C3—C4—H4119.0C19—C20—H20118.9
C4—C5—C6116.3 (2)C20—C21—C22116.3 (2)
C4—C5—H5121.8C20—C21—H21121.9
C6—C5—H5121.8C22—C21—H21121.9
N2—C6—C5132.1 (2)N3—C22—C21133.0 (2)
N2—C6—C1105.54 (19)N3—C22—C17105.2 (2)
C5—C6—C1122.4 (2)C21—C22—C17121.8 (2)
N1—C7—N2112.6 (2)O1—C23—N5126.3 (4)
N1—C7—H7123.7O1—C23—H23116.8
N2—C7—H7123.7N5—C23—H23116.8
N2—C8—C9110.68 (19)N5—C24—H24A109.5
N2—C8—H8A109.5N5—C24—H24B109.5
C9—C8—H8A109.5H24A—C24—H24B109.5
N2—C8—H8B109.5N5—C24—H24C109.5
C9—C8—H8B109.5H24A—C24—H24C109.5
H8A—C8—H8B108.1H24B—C24—H24C109.5
C14—C9—C10118.9 (2)N5—C25—H25A109.5
C14—C9—C8120.7 (2)N5—C25—H25B109.5
C10—C9—C8120.4 (2)H25A—C25—H25B109.5
C11—C10—C9121.0 (2)N5—C25—H25C109.5
C11—C10—H10119.5H25A—C25—H25C109.5
C9—C10—H10119.5H25B—C25—H25C109.5
N4i—Zn1—N1—C7−101.91 (19)C9—C10—C11—C15−178.8 (2)
Cl2—Zn1—N1—C717.5 (2)C10—C11—C12—C13−0.6 (4)
Cl1—Zn1—N1—C7151.65 (17)C15—C11—C12—C13179.9 (2)
N4i—Zn1—N1—C164.00 (19)C11—C12—C13—C14−0.9 (4)
Cl2—Zn1—N1—C1−176.59 (17)C10—C9—C14—C13−0.2 (4)
Cl1—Zn1—N1—C1−42.44 (19)C8—C9—C14—C13−178.1 (2)
C7—N1—C1—C6−0.1 (2)C12—C13—C14—C91.3 (4)
Zn1—N1—C1—C6−168.31 (15)C16—N3—C15—C11128.1 (2)
C7—N1—C1—C2−179.8 (2)C22—N3—C15—C11−59.4 (3)
Zn1—N1—C1—C212.0 (3)C10—C11—C15—N3112.2 (2)
N1—C1—C2—C3−179.9 (2)C12—C11—C15—N3−68.3 (3)
C6—C1—C2—C30.5 (3)C17—N4—C16—N3−0.5 (3)
C1—C2—C3—C4−0.3 (4)Zn1i—N4—C16—N3−164.84 (16)
C2—C3—C4—C50.0 (4)C22—N3—C16—N40.6 (3)
C3—C4—C5—C60.0 (4)C15—N3—C16—N4174.3 (2)
C7—N2—C6—C5−179.8 (2)C16—N4—C17—C18179.7 (2)
C8—N2—C6—C5−3.4 (4)Zn1i—N4—C17—C18−17.1 (4)
C7—N2—C6—C10.0 (2)C16—N4—C17—C220.3 (3)
C8—N2—C6—C1176.4 (2)Zn1i—N4—C17—C22163.61 (17)
C4—C5—C6—N2180.0 (2)C22—C17—C18—C19−0.3 (4)
C4—C5—C6—C10.1 (3)N4—C17—C18—C19−179.6 (2)
N1—C1—C6—N20.0 (2)C17—C18—C19—C200.0 (4)
C2—C1—C6—N2179.7 (2)C18—C19—C20—C21−0.1 (4)
N1—C1—C6—C5179.9 (2)C19—C20—C21—C220.4 (4)
C2—C1—C6—C5−0.4 (4)C16—N3—C22—C21179.6 (3)
C1—N1—C7—N20.1 (3)C15—N3—C22—C216.1 (4)
Zn1—N1—C7—N2168.44 (15)C16—N3—C22—C17−0.3 (3)
C6—N2—C7—N1−0.1 (3)C15—N3—C22—C17−173.8 (2)
C8—N2—C7—N1−176.5 (2)C20—C21—C22—N3179.4 (3)
C7—N2—C8—C9115.4 (2)C20—C21—C22—C17−0.7 (4)
C6—N2—C8—C9−60.3 (3)C18—C17—C22—N3−179.4 (2)
N2—C8—C9—C14125.4 (2)N4—C17—C22—N30.0 (3)
N2—C8—C9—C10−52.4 (3)C18—C17—C22—C210.7 (4)
C14—C9—C10—C11−1.3 (4)N4—C17—C22—C21−179.9 (2)
C8—C9—C10—C11176.5 (2)C25—N5—C23—O1−176.3 (3)
C9—C10—C11—C121.7 (3)C24—N5—C23—O12.7 (5)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2441).

References

  • Aakeröy, C. B., Desper, J., Elisabeth, E., Helfrich, B. A., Levin, B. & Urbina, J. F. (2005). Z. Kristallogr.200, 325–332.
  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Fan, J., Yee, G. T., Wang, G. & Hanson, B. E. (2006). Inorg. Chem.45, 599–608. [PubMed]
  • Raehm, L., Mimassi, L., Guyard-Duhayon, C. & Amouri, H. (2003). Inorg. Chem.42, 5654–5659. [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.

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