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

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Substitutional disorder in a hypervalent diorganotin(IV) dihalide

aFaculty of Chemistry and Chemical Engineering, Babes-Bolyai University, Arany Janos Str. no. 11, RO-400028, Cluj Napoca, Romania
*Correspondence e-mail: richy@chem.ubbcluj.ro

(Received 22 November 2007; accepted 26 November 2007; online 6 December 2007)

The structure of bromidochloridobis[2-(dimethyl­amino­meth­yl)phen­yl]tin(IV), [SnBr0.65Cl1.35(C9H12N)2], contains two 2-(Me2NCH2)C6H4 units bonded to a Sn atom which lies on a twofold axis. The compound exhibits substitutional disorder of the halide atoms bonded to the Sn, with 1.35 occupancy for Cl and 0.65 for Br; it is isomorphous with the corresponding dichloride. The Sn atom is hexa­coordinated with a (C,N)2SnX2 (X = Cl/Br) distorted octa­hedral core as a result of the strong intra­molecular N→Sn coordination trans to the Sn—X bonds (N1—Sn1—X1 = 165.8°). As a result of the inter­molecular contacts, viz. H⋯X and H⋯benzene inter­actions, the mol­ecules are arranged in a three-dimensional supra­molecular manner in the crystal structure.

Related literature

For related literature see Varga et al. (2001[Varga, R. A., Schuermann, M. & Silvestru, C. (2001). J. Organomet. Chem. 623, 161-167.], 2005[Varga, R. A., Silvestru, C. & Deleanu, C. (2005). Appl. Organomet. Chem. 19, 153-160.], 2006[Varga, R. A., Rotar, A., Schuermann, M., Jurkschat, K. & Silvestru, C. (2006). Eur. J. Inorg. Chem. 7, 1475-1486.], 2007[Varga, R. A. & Silvestru, C. (2007). Acta Cryst. C63, m48-m50.]); Rotar et al. (2007[Rotar, A., Varga, R. A. & Silvestru, C. (2007). Acta Cryst. C63, m355-m356.]); Emsley (1994[Emsley, J. (1994). Die Elemente. Berlin: Walter de Gruyter.]); IUPAC (1979[IUPAC (1979). Nomenclature of Organic Chemistry. Oxford: Pergamon Press.]).

[Scheme 1]

Experimental

Crystal data
  • [SnBr0.65Cl1.35(C9H12N)2]

  • Mr = 486.89

  • Monoclinic, C 2/c

  • a = 17.0221 (15) Å

  • b = 8.2387 (7) Å

  • c = 14.7510 (13) Å

  • β = 106.1050 (10)°

  • V = 1987.5 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 2.78 mm−1

  • T = 297 (2) K

  • 0.32 × 0.25 × 0.11 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SAINT-Plus; Bruker, 2000[Bruker (2000). SMART (Version 5.625) and SAINT-Plus (Version 6.29). Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.452, Tmax = 0.738

  • 6916 measured reflections

  • 1746 independent reflections

  • 1693 reflections with I > 2σ(I)

  • Rint = 0.035

Refinement
  • R[F2 > 2σ(F2)] = 0.027

  • wR(F2) = 0.060

  • S = 1.24

  • 1746 reflections

  • 108 parameters

  • H-atom parameters constrained

  • Δρmax = 0.36 e Å−3

  • Δρmin = −0.47 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C3—H3⋯Cg1ii 0.93 3.19 3.78 (1) 123
C4—H4⋯Cl1ii/Br1ii 0.93 2.87 3.798 (5) 173
C6—H6⋯Cl1iii/Br1iii 0.93 3.02 3.710 (3) 132
Symmetry code: (ii) [-{\script{1\over 2}}+x], [{\script{1\over 2}}+y], z, (iii) 2-x, 1-y, 1-z. Cg1 is the centroid of the benzene ring C1–C6.

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART (Version 5.625) and SAINT-Plus (Version 6.29). Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2000[Bruker (2000). SMART (Version 5.625) and SAINT-Plus (Version 6.29). Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Bruker, 2001[Bruker (2001). SHELXTL. Version 6.10.12. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2007[Westrip, S. P. (2007). publCIF. In preparation.]).

Supporting information


Comment top

During our work on hypervalent organotin(IV) compounds with the [2-(Me2NCH2)C6H4]Sn fragment (Varga et al., 2001, 2005, 2006, 2007, Rotar et al. 2007), the title compound (I) was isolated. It contains two 2-(Me2NCH2)C6H4 units bonded to a tin atom which lies on a twofold axis of the space group C2/c. The compound exhibits substitutional disorder of both halide atoms bonded to the Sn with chlorine being the major (1.35) and the bromine the minor (0.65) component.

The structure of [2-(Me2NCH2)C6H4]2SnCl2 was also determined (Varga et al., 2001) and is isomorphous with the title compound. Both have space group C2/c; the cell constants as well as the volume differ slightly (0.39% increase for the title compound) as the result of the presence of a different halide in the molecular unit.

The molecules of the compound feature a metal atom strongly coordinated by two nitrogen atoms of the pendant arms [Sn—N1 = 2.64 (1) Å; the Sn—N distance exceeds the sum of the covalent radii for the corresponding atoms, Σcov(Sn,N) = 2.1 Å (Emsley, 1994)] trans to an Sn–halogen bond (N1—Sn1—X1 = 165.8°). This results in a (C,N)2SnX2 (X = Cl/Br) core in the title compound with a trans-SnC2 fragment, while the N and X atoms are cis positions (Fig. 1). The octahedral geometry around the Sn atom is distorted from the ideal geometry as a consequence of the small 'bite' of the pendant arm ligand [C1—Sn1—N1 = 71.4°] and the steric repulsion between the organic groups bonded to the Sn atoms. All these features are similar to the corresponding dichloride.

As a result of the intramolecular coordination of the nitrogen to the tin atom a five-membered SnC3N ring is formed. This ring is not planar but is folded along the Sn(1)···Cmethylene axis with the N atom out of the best plane defined by the residual SnC3, thus inducing planar chirality, with the phenyl ring as chiral plane and the nitrogen as pilot atom (IUPAC, 1979). Indeed, the compound crystallizes as a racemate, i.e. a mixture of RN1RN1i and SN1SN1i [symmetry code: (i) 2 - x, y, 0.5 - z].

In the crystal of the title compound intermolecular interactions, i.e. hydrogen bond type interactions and H···phenyl interactions (Fig. 2), give rise to a supramolecular array. If only chlorine is considered than layers are built of the same type of isomer [H4···X1ii = 2.87 Å, H3···Cg1ii = 3.19 Å; symmetry code: (ii) -1/2 + x, 1/2 + y, z] along the ab plane (Fig. 3). If bromine is taken into account, than alternating parallel layers of RN1RN1i and SN1SN1i isomers are bridged through weak H6···X1iii [3.02 Å; symmetry code: (iii) 2 - x, 1 - y, 1 - z] interactions resulting in a three-dimensional supramolecular architecture (Fig. 4).

Related literature top

For related literature see Varga et al. (2001, 2005, 2006, 2007); Rotar et al. (2007); Emsley (1994); IUPAC (1979).

Experimental top

The title compound was isolated as a by-product of the reaction between [2-(Me2NCH2)C6H4]SnCl2 and [2,6-(Me)2C6H3]MgBr, due to partial halide exchange.

Refinement top

All hydrogen atoms were placed in calculated positions using a riding model, with C—H = 0.93–0.97 Å and with Uiso= 1.5Ueq (C) for methyl H and Uiso= 1.2Ueq (C) for aryl H. The methyl groups were allowed to rotate but not to tip. The two halide atoms were refined as substitutional disorder between chlorine and bromine, with 1.35 occupancy for Cl and 0.65 occupancy for Br.

Structure description top

During our work on hypervalent organotin(IV) compounds with the [2-(Me2NCH2)C6H4]Sn fragment (Varga et al., 2001, 2005, 2006, 2007, Rotar et al. 2007), the title compound (I) was isolated. It contains two 2-(Me2NCH2)C6H4 units bonded to a tin atom which lies on a twofold axis of the space group C2/c. The compound exhibits substitutional disorder of both halide atoms bonded to the Sn with chlorine being the major (1.35) and the bromine the minor (0.65) component.

The structure of [2-(Me2NCH2)C6H4]2SnCl2 was also determined (Varga et al., 2001) and is isomorphous with the title compound. Both have space group C2/c; the cell constants as well as the volume differ slightly (0.39% increase for the title compound) as the result of the presence of a different halide in the molecular unit.

The molecules of the compound feature a metal atom strongly coordinated by two nitrogen atoms of the pendant arms [Sn—N1 = 2.64 (1) Å; the Sn—N distance exceeds the sum of the covalent radii for the corresponding atoms, Σcov(Sn,N) = 2.1 Å (Emsley, 1994)] trans to an Sn–halogen bond (N1—Sn1—X1 = 165.8°). This results in a (C,N)2SnX2 (X = Cl/Br) core in the title compound with a trans-SnC2 fragment, while the N and X atoms are cis positions (Fig. 1). The octahedral geometry around the Sn atom is distorted from the ideal geometry as a consequence of the small 'bite' of the pendant arm ligand [C1—Sn1—N1 = 71.4°] and the steric repulsion between the organic groups bonded to the Sn atoms. All these features are similar to the corresponding dichloride.

As a result of the intramolecular coordination of the nitrogen to the tin atom a five-membered SnC3N ring is formed. This ring is not planar but is folded along the Sn(1)···Cmethylene axis with the N atom out of the best plane defined by the residual SnC3, thus inducing planar chirality, with the phenyl ring as chiral plane and the nitrogen as pilot atom (IUPAC, 1979). Indeed, the compound crystallizes as a racemate, i.e. a mixture of RN1RN1i and SN1SN1i [symmetry code: (i) 2 - x, y, 0.5 - z].

In the crystal of the title compound intermolecular interactions, i.e. hydrogen bond type interactions and H···phenyl interactions (Fig. 2), give rise to a supramolecular array. If only chlorine is considered than layers are built of the same type of isomer [H4···X1ii = 2.87 Å, H3···Cg1ii = 3.19 Å; symmetry code: (ii) -1/2 + x, 1/2 + y, z] along the ab plane (Fig. 3). If bromine is taken into account, than alternating parallel layers of RN1RN1i and SN1SN1i isomers are bridged through weak H6···X1iii [3.02 Å; symmetry code: (iii) 2 - x, 1 - y, 1 - z] interactions resulting in a three-dimensional supramolecular architecture (Fig. 4).

For related literature see Varga et al. (2001, 2005, 2006, 2007); Rotar et al. (2007); Emsley (1994); IUPAC (1979).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART (Bruker, 2000); data reduction: SAINT-Plus (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL (Bruker, 2001); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2007).

Figures top
[Figure 1] Fig. 1. : A view of title compound showing the atom-numbering scheme at 30% probability thermal ellipsoids for (RN,RNi)-(I) isomer [symmetry code: (i) 2 - x, y, 0.5 - z]. H atoms are drawn as spheres of arbitrary radii.
[Figure 2] Fig. 2. : Intermolecular interactions [shown as dashed lines, black for H···X (X = Cl/Br), red for H···phenyl]. Only H involved in interactions are showed. Symmetry codes: (i) 2 - x, y, 0.5 - z, (ii) -1/2 + x, 1/2 + y, z, (iii) 2 - x, 1 - y, 1 - z.
[Figure 3] Fig. 3. : View of the two-dimensional layer formed through H···X and H···phenyl interactions along c axis. Only H involved in interactions are showed.
[Figure 4] Fig. 4. : Crystal packing showing the three-dimensional supramolecular architecture along a axis. Only H involved in interactions are showed.
bromidochloridobis[2-(dimethylaminomethyl)phenyl]tin(IV) top
Crystal data top
[SnBr0.65Cl1.35(C9H12N)2]F(000) = 966.8
Mr = 486.89Dx = 1.627 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 3754 reflections
a = 17.0221 (15) Åθ = 2.5–26.9°
b = 8.2387 (7) ŵ = 2.78 mm1
c = 14.7510 (13) ÅT = 297 K
β = 106.105 (1)°Block, colourless
V = 1987.5 (3) Å30.32 × 0.25 × 0.11 mm
Z = 4
Data collection top
Bruker Smart APEX CCD area-detector
diffractometer
1746 independent reflections
Radiation source: fine-focus sealed tube1693 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
phi and ω scansθmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan
(SAINT-Plus; Bruker, 2000)
h = 1920
Tmin = 0.452, Tmax = 0.738k = 99
6916 measured reflectionsl = 1717
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.027Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.060H-atom parameters constrained
S = 1.24 w = 1/[σ2(Fo2) + (0.P)2 + 3.2594P]
where P = (Fo2 + 2Fc2)/3
1746 reflections(Δ/σ)max = 0.001
108 parametersΔρmax = 0.36 e Å3
0 restraintsΔρmin = 0.47 e Å3
Crystal data top
[SnBr0.65Cl1.35(C9H12N)2]V = 1987.5 (3) Å3
Mr = 486.89Z = 4
Monoclinic, C2/cMo Kα radiation
a = 17.0221 (15) ŵ = 2.78 mm1
b = 8.2387 (7) ÅT = 297 K
c = 14.7510 (13) Å0.32 × 0.25 × 0.11 mm
β = 106.105 (1)°
Data collection top
Bruker Smart APEX CCD area-detector
diffractometer
1746 independent reflections
Absorption correction: multi-scan
(SAINT-Plus; Bruker, 2000)
1693 reflections with I > 2σ(I)
Tmin = 0.452, Tmax = 0.738Rint = 0.035
6916 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0270 restraints
wR(F2) = 0.060H-atom parameters constrained
S = 1.24Δρmax = 0.36 e Å3
1746 reflectionsΔρmin = 0.47 e Å3
108 parameters
Special details top

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) top
xyzUiso*/UeqOcc. (<1)
Br11.04832 (5)0.42622 (9)0.36987 (5)0.0721 (3)0.325 (3)
Cl11.04832 (5)0.42622 (9)0.36987 (5)0.0721 (3)0.675 (3)
Sn11.00000.64336 (4)0.25000.03453 (12)
C10.89182 (18)0.7072 (4)0.2862 (2)0.0386 (7)
C60.8831 (2)0.6785 (4)0.3757 (2)0.0455 (8)
H60.92540.62930.42120.055*
C20.8274 (2)0.7761 (5)0.2181 (3)0.0517 (9)
C50.8125 (2)0.7221 (5)0.3982 (3)0.0589 (10)
H50.80720.70220.45830.071*
C40.7506 (3)0.7942 (6)0.3318 (3)0.0714 (12)
H40.70350.82600.34720.086*
C30.7572 (2)0.8206 (6)0.2424 (3)0.0707 (12)
H30.71410.86880.19750.085*
N10.91474 (19)0.8322 (4)0.1136 (2)0.0547 (8)
C70.8321 (2)0.7923 (6)0.1177 (3)0.0653 (11)
H7A0.81500.69110.08450.078*
H7B0.79470.87660.08600.078*
C80.9324 (3)1.0031 (5)0.1373 (3)0.0785 (13)
H8A0.89541.07000.09150.118*
H8B0.98761.02690.13710.118*
H8C0.92591.02460.19870.118*
C90.9204 (3)0.8054 (7)0.0157 (3)0.0838 (15)
H9A0.88100.87240.02730.126*
H9B0.90960.69340.00120.126*
H9C0.97440.83310.01240.126*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0787 (5)0.0714 (5)0.0805 (6)0.0373 (4)0.0458 (4)0.0378 (4)
Cl10.0787 (5)0.0714 (5)0.0805 (6)0.0373 (4)0.0458 (4)0.0378 (4)
Sn10.03419 (18)0.03473 (18)0.04017 (19)0.0000.01949 (13)0.000
C10.0344 (16)0.0371 (17)0.0486 (19)0.0027 (13)0.0187 (15)0.0014 (14)
C60.0446 (19)0.048 (2)0.050 (2)0.0021 (15)0.0240 (16)0.0028 (16)
C20.0413 (19)0.061 (2)0.056 (2)0.0070 (17)0.0187 (17)0.0090 (18)
C50.058 (2)0.068 (3)0.063 (2)0.003 (2)0.036 (2)0.002 (2)
C40.052 (2)0.084 (3)0.093 (3)0.015 (2)0.045 (2)0.002 (3)
C30.044 (2)0.082 (3)0.089 (3)0.018 (2)0.023 (2)0.013 (2)
N10.0518 (18)0.068 (2)0.0470 (17)0.0091 (15)0.0181 (14)0.0161 (15)
C70.045 (2)0.088 (3)0.059 (2)0.009 (2)0.0076 (18)0.019 (2)
C80.090 (3)0.062 (3)0.085 (3)0.004 (2)0.026 (3)0.022 (2)
C90.084 (3)0.121 (4)0.050 (2)0.019 (3)0.024 (2)0.030 (3)
Geometric parameters (Å, º) top
Br1—Sn12.4893 (7)C4—H40.9300
Sn1—C12.121 (3)C3—H30.9300
Sn1—C1i2.121 (3)N1—C71.462 (5)
Sn1—Cl1i2.4893 (7)N1—C81.462 (5)
Sn1—Br1i2.4893 (7)N1—C91.491 (5)
C1—C21.387 (5)C7—H7A0.9700
C1—C61.389 (5)C7—H7B0.9700
C6—C51.380 (5)C8—H8A0.9600
C6—H60.9300C8—H8B0.9600
C2—C31.389 (5)C8—H8C0.9600
C2—C71.510 (5)C9—H9A0.9600
C5—C41.360 (6)C9—H9B0.9600
C5—H50.9300C9—H9C0.9600
C4—C31.372 (6)
C1—Sn1—C1i151.30 (17)C4—C3—C2120.8 (4)
C1—Sn1—Cl1i102.61 (9)C4—C3—H3119.6
C1i—Sn1—Cl1i97.93 (9)C2—C3—H3119.6
C1—Sn1—Br1i102.61 (9)C7—N1—C8110.1 (3)
C1i—Sn1—Br1i97.93 (9)C7—N1—C9109.2 (3)
Cl1i—Sn1—Br1i0.00 (4)C8—N1—C9108.0 (3)
C1—Sn1—Br197.93 (9)N1—C7—C2112.0 (3)
C1i—Sn1—Br1102.61 (9)N1—C7—H7A109.2
Cl1i—Sn1—Br188.11 (4)C2—C7—H7A109.2
Br1i—Sn1—Br188.11 (4)N1—C7—H7B109.2
C2—C1—C6119.2 (3)C2—C7—H7B109.2
C2—C1—Sn1119.1 (2)H7A—C7—H7B107.9
C6—C1—Sn1121.8 (2)N1—C8—H8A109.5
C5—C6—C1120.9 (3)N1—C8—H8B109.5
C5—C6—H6119.6H8A—C8—H8B109.5
C1—C6—H6119.6N1—C8—H8C109.5
C1—C2—C3119.0 (4)H8A—C8—H8C109.5
C1—C2—C7120.0 (3)H8B—C8—H8C109.5
C3—C2—C7120.9 (3)N1—C9—H9A109.5
C4—C5—C6119.6 (4)N1—C9—H9B109.5
C4—C5—H5120.2H9A—C9—H9B109.5
C6—C5—H5120.2N1—C9—H9C109.5
C5—C4—C3120.5 (4)H9A—C9—H9C109.5
C5—C4—H4119.7H9B—C9—H9C109.5
C3—C4—H4119.7
C1i—Sn1—C1—C270.1 (3)C6—C1—C2—C7173.7 (4)
Cl1i—Sn1—C1—C264.6 (3)Sn1—C1—C2—C74.9 (5)
Br1i—Sn1—C1—C264.6 (3)C1—C6—C5—C40.1 (6)
Br1—Sn1—C1—C2154.4 (3)C6—C5—C4—C31.5 (7)
C1i—Sn1—C1—C6111.4 (3)C5—C4—C3—C20.8 (7)
Cl1i—Sn1—C1—C6113.9 (3)C1—C2—C3—C41.3 (7)
Br1i—Sn1—C1—C6113.9 (3)C7—C2—C3—C4175.0 (4)
Br1—Sn1—C1—C624.1 (3)C8—N1—C7—C275.8 (4)
C2—C1—C6—C52.0 (5)C9—N1—C7—C2165.8 (4)
Sn1—C1—C6—C5179.5 (3)C1—C2—C7—N137.0 (5)
C6—C1—C2—C32.6 (6)C3—C2—C7—N1146.8 (4)
Sn1—C1—C2—C3178.8 (3)
Symmetry code: (i) x+2, y, z+1/2.

Experimental details

Crystal data
Chemical formula[SnBr0.65Cl1.35(C9H12N)2]
Mr486.89
Crystal system, space groupMonoclinic, C2/c
Temperature (K)297
a, b, c (Å)17.0221 (15), 8.2387 (7), 14.7510 (13)
β (°) 106.105 (1)
V3)1987.5 (3)
Z4
Radiation typeMo Kα
µ (mm1)2.78
Crystal size (mm)0.32 × 0.25 × 0.11
Data collection
DiffractometerBruker Smart APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SAINT-Plus; Bruker, 2000)
Tmin, Tmax0.452, 0.738
No. of measured, independent and
observed [I > 2σ(I)] reflections
6916, 1746, 1693
Rint0.035
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.027, 0.060, 1.24
No. of reflections1746
No. of parameters108
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.36, 0.47

Computer programs: SMART (Bruker, 2000), SAINT-Plus (Bruker, 2000), SHELXTL (Bruker, 2001), DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2007).

Y—H···π-ring interactions. top
Y—H···CgY—HH···CgY···CgY—H···Cg
C3—H3···Cg1ii0.933.193.78 (1)123
Symmetry code: (ii) -1/2 + x, 1/2 + y, z. Cg1 is the centroid of the benzene ring C1–C6.
Hydrogen-bond geometry (Å, °) top
D-H···AD-HH···AD···AD-H···A
C4-H4···Cl1ii/Br1ii0.932.873.798 (5)173
C6-H6···Cl1iii/Br1iii0.933.023.710 (3)132
Symmetry code: (ii) -0.5+x, 0.5+y, z, (iii) 2-x, 1-y, 1-z.
 

Acknowledgements

Financial support from the National University Research Council (CEEX 63/2006) is greatly appreciated. We also thank the National Center for X-Ray Diffraction, Cluj-Napoca, for help with the solid-state structure determination.

References

First citationBrandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
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