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

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ISSN: 2056-9890

1,3-Bis(2,6-diiso­propyl­phen­yl)-1H-imidazol-3-ium bromide di­chloro­methane disolvate

aInstitut für Anorganische und Analytische Chemie, Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt am Main, Germany
*Correspondence e-mail: bolte@chemie.uni-frankfurt.de

(Received 10 May 2012; accepted 16 May 2012; online 23 May 2012)

In the title compound, C27H37N2+·Br·2CH2Cl2, both the cation and the anion are located on a crystallographic mirror plane. Both of the dichloro­methane solvent mol­ecules show a disorder across a mirror plane over two equally occupied positions. In the crystal, the cations are connnected to the bromide ions via C—H⋯Br hydrogen bonds.

Related literature

For the preparation of imidazolium salts, see: Arduengo et al. (1995[Arduengo, A. J., Goerlich, J. R. & Marshall, W. J. (1995). J. Am. Chem. Soc. 117, 11027-11028.], 1999[Arduengo, A. J., Krafczyk, R., Schmutzler, R., Craig, H. A., Goerlich, J. R., Marshall, W. J. & Unverzagt, M. (1999). Tetrahedron, 55, 14523-14534.]); Hinter­mann (2007[Hintermann, L. (2007). Beilstein J. Org. Chem. 3 No. 22. doi:10.1186/1860-5397-3-22.]). For structures with the same cation but different anions, see: Stasch et al. (2004[Stasch, A., Singh, S., Roesky, H. W., Noltemeyer, M. & Schmidt, H.-G. (2004). Eur. J. Inorg. Chem. pp. 4052-4055.]); Blue et al. (2006[Blue, E. D., Gunnoe, T. B., Petersen, J. L. & Boyle, P. D. (2006). J. Organomet. Chem. 691, 5988-5993.]); Berger et al. (2012[Berger, M., Auner, N. & Bolte, M. (2012). Acta Cryst. E68, o1844.]). For compounds with the 1,3-bis-(2,6-diisopropyl­phen­yl)imidazolium unit, see: Ikhile et al. (2010[Ikhile, M. I. & Bala, M. D. (2010). Acta Cryst. E66, o3121.]); Giffin et al. (2010[Giffin, N. A., Hendsbee, A. D. & Masuda, J. D. (2010). Acta Cryst. E66, o2090-o2091.]).

[Scheme 1]

Experimental

Crystal data
  • C27H37N2+·Br·2CH2Cl2

  • Mr = 639.35

  • Monoclinic, P 21 /m

  • a = 9.1874 (8) Å

  • b = 16.5165 (12) Å

  • c = 11.030 (1) Å

  • β = 102.332 (7)°

  • V = 1635.1 (2) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 1.60 mm−1

  • T = 173 K

  • 0.52 × 0.28 × 0.24 mm

Data collection
  • Stoe IPDS II two-circle diffractometer

  • Absorption correction: multi-scan (MULABS; Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]; Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]) Tmin = 0.489, Tmax = 0.700

  • 20988 measured reflections

  • 3200 independent reflections

  • 2867 reflections with I > 2σ(I)

  • Rint = 0.084

Refinement
  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.090

  • S = 1.03

  • 3200 reflections

  • 197 parameters

  • H-atom parameters constrained

  • Δρmax = 0.43 e Å−3

  • Δρmin = −0.36 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C1—H1⋯Br1 0.95 2.59 3.538 (3) 175

Data collection: X-AREA (Stoe & Cie, 2001[Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97 .

Supporting information


Comment top

Imidazolium salts are precursors for the synthesis of N-heterocyclic carbenes (NHC) and can be prepared according to Arduengo et al. (1995, 1999) and Hintermann (2007). Deprotonation by strong bases gives the free stable NHC, which is widely used as ligands.

The title compound crystallizes with discrete cations, anions and solvent dichloromethane molecules. Both cations and anions are located on a crystallographic mirror plane. Both dichloromethane molecules show a disorder across a mirror plane over two equally occupied positions. The Br anions are connnected to the cations via C—H···Br hydrogen bonds. Structures with the same cation, but with different anions and solvent molecules, have been determined by Stasch et al. (2004), Blue et al. (2006) and Berger et al. (2012). For compounds with 1,3-bis-(2,6-diisopropylphenyl)imidazolium unit, see: Ikhile et al. (2010) and Giffin et al. (2010).

Related literature top

For the preparation of imidazolium salts, see: Arduengo et al. (1995, 1999); Hintermann (2007). For structures with the same cation but different anions, see: Stasch et al. (2004); Blue et al. (2006); Berger et al. (2012). For compounds with the 1,3-bis-(2,6-diisopropylphenyl)imidazolium unit, see: Ikhile et al. (2010); Giffin et al. (2010).

Experimental top

1,3-Bis(2,6-di-isopropylphenyl)1H-imidazol-3-ium bromide chloroform disolvate was prepared by reacting 167 mg of 1,3-bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene with 115 mg of Si2Br6 in deuterated dichloromethane. After two weeks at 253 K colorless needles of the title compound crystallized in the NMR-Tube.

Refinement top

H atoms were refined using a riding model, with C—H ranging from 0.95 Å to 1.00 Å and with Uiso(H) = 1.2Ueq(C) or Uiso(H) = 1.5Ueq(Cmethyl).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A perspective view of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding and dichloromethane molecules are omitted for clarity. Atoms labelled with suffix A were generated by the symmetry operator x, -y + 1/2, z.
1,3-Bis(2,6-diisopropylphenyl)-1H-imidazol-3-ium bromide dichloromethane disolvate top
Crystal data top
C27H37N2+·Br·2CH2Cl2F(000) = 664
Mr = 639.35Dx = 1.299 Mg m3
Monoclinic, P21/mMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybCell parameters from 19135 reflections
a = 9.1874 (8) Åθ = 3.4–26.0°
b = 16.5165 (12) ŵ = 1.60 mm1
c = 11.030 (1) ÅT = 173 K
β = 102.332 (7)°Plate, colourless
V = 1635.1 (2) Å30.52 × 0.28 × 0.24 mm
Z = 2
Data collection top
Stoe IPDS II two-circle
diffractometer
3200 independent reflections
Radiation source: Genix 3D IµS microfocus X-ray source2867 reflections with I > 2σ(I)
Genix 3D multilayer optics monochromatorRint = 0.084
ω scansθmax = 25.7°, θmin = 3.4°
Absorption correction: multi-scan
(MULABS; Spek, 2009; Blessing, 1995)
h = 1111
Tmin = 0.489, Tmax = 0.700k = 1920
20988 measured reflectionsl = 1313
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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.041P)2 + 0.9357P]
where P = (Fo2 + 2Fc2)/3
3200 reflections(Δ/σ)max < 0.001
197 parametersΔρmax = 0.43 e Å3
0 restraintsΔρmin = 0.36 e Å3
Crystal data top
C27H37N2+·Br·2CH2Cl2V = 1635.1 (2) Å3
Mr = 639.35Z = 2
Monoclinic, P21/mMo Kα radiation
a = 9.1874 (8) ŵ = 1.60 mm1
b = 16.5165 (12) ÅT = 173 K
c = 11.030 (1) Å0.52 × 0.28 × 0.24 mm
β = 102.332 (7)°
Data collection top
Stoe IPDS II two-circle
diffractometer
3200 independent reflections
Absorption correction: multi-scan
(MULABS; Spek, 2009; Blessing, 1995)
2867 reflections with I > 2σ(I)
Tmin = 0.489, Tmax = 0.700Rint = 0.084
20988 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.090H-atom parameters constrained
S = 1.03Δρmax = 0.43 e Å3
3200 reflectionsΔρmin = 0.36 e Å3
197 parameters
Special details top

Experimental. ;

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)
N10.29660 (18)0.18481 (10)0.41051 (15)0.0255 (4)
C10.2134 (3)0.25000.4158 (3)0.0241 (6)
H10.11190.25000.42220.029*
C20.4378 (2)0.20927 (14)0.4033 (2)0.0313 (5)
H20.51970.17510.39920.038*
C30.1307 (3)0.11525 (15)0.1796 (2)0.0440 (6)
H30.18460.16820.19250.053*
C40.0359 (4)0.1327 (2)0.1415 (3)0.0594 (8)
H4A0.05670.16260.06290.089*
H4B0.06690.16520.20590.089*
H4C0.09110.08150.13110.089*
C50.1838 (3)0.0696 (2)0.0773 (3)0.0545 (7)
H5A0.16070.10120.00040.082*
H5B0.13330.01710.06400.082*
H5C0.29170.06110.10170.082*
C60.3631 (3)0.09778 (16)0.6435 (2)0.0394 (5)
H60.41380.14700.61970.047*
C70.2619 (4)0.1250 (3)0.7253 (4)0.0934 (15)
H7A0.18680.16210.67910.140*
H7B0.32030.15290.79800.140*
H7C0.21230.07790.75230.140*
C80.4824 (5)0.0423 (3)0.7119 (4)0.1023 (17)
H8A0.54720.02560.65650.153*
H8B0.43610.00570.74010.153*
H8C0.54150.07070.78380.153*
C110.2443 (2)0.10184 (13)0.4124 (2)0.0317 (5)
C120.1641 (3)0.06934 (14)0.3013 (2)0.0382 (5)
C130.1118 (4)0.00958 (16)0.3072 (3)0.0531 (7)
H130.05590.03430.23420.064*
C140.1396 (4)0.05222 (16)0.4166 (3)0.0578 (8)
H140.10190.10570.41830.069*
C150.2209 (3)0.01857 (16)0.5234 (3)0.0500 (7)
H150.24010.04940.59780.060*
C160.2761 (3)0.06008 (14)0.5248 (2)0.0366 (5)
Br10.17082 (3)0.25000.41902 (3)0.03239 (11)
C90.6207 (8)0.2781 (5)0.1008 (6)0.083 (4)0.50
H9A0.66870.27350.18990.100*0.309 (13)
H9B0.69870.26570.05400.100*0.309 (13)
H9C0.68250.25610.04520.100*0.191 (13)
H9D0.66660.26610.18860.100*0.191 (13)
Cl10.5757 (3)0.3808 (3)0.0739 (3)0.1306 (12)0.50
Cl20.4398 (9)0.25000.0600 (7)0.091 (3)0.38 (3)
Cl2'0.4863 (16)0.1966 (13)0.0681 (6)0.129 (7)0.309 (13)
C100.7893 (8)0.2231 (4)0.7366 (6)0.0643 (18)0.50
H10A0.77760.23630.64750.077*0.50
H10B0.77600.16390.74380.077*0.50
Cl30.96814 (15)0.25000.81560 (13)0.0802 (4)
Cl40.6535 (2)0.27308 (11)0.79502 (16)0.0803 (7)0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0245 (9)0.0254 (8)0.0255 (8)0.0012 (7)0.0030 (7)0.0009 (7)
C10.0239 (14)0.0225 (14)0.0246 (14)0.0000.0022 (11)0.000
C20.0247 (10)0.0374 (11)0.0322 (11)0.0053 (9)0.0074 (8)0.0019 (9)
C30.0606 (16)0.0333 (12)0.0331 (12)0.0058 (12)0.0012 (11)0.0042 (10)
C40.074 (2)0.0622 (19)0.0383 (14)0.0213 (16)0.0033 (13)0.0042 (13)
C50.0549 (17)0.0630 (18)0.0446 (15)0.0006 (15)0.0085 (13)0.0039 (14)
C60.0428 (13)0.0418 (13)0.0325 (12)0.0040 (11)0.0055 (10)0.0051 (10)
C70.057 (2)0.142 (4)0.081 (3)0.000 (2)0.0153 (19)0.065 (3)
C80.100 (3)0.100 (3)0.080 (3)0.056 (3)0.042 (2)0.025 (2)
C110.0341 (12)0.0226 (10)0.0381 (12)0.0013 (9)0.0073 (9)0.0009 (9)
C120.0456 (14)0.0276 (11)0.0384 (12)0.0020 (10)0.0025 (10)0.0018 (10)
C130.071 (2)0.0321 (13)0.0501 (16)0.0120 (13)0.0003 (14)0.0050 (12)
C140.081 (2)0.0268 (13)0.0620 (18)0.0124 (13)0.0074 (16)0.0036 (12)
C150.0673 (19)0.0345 (13)0.0484 (15)0.0004 (13)0.0128 (14)0.0118 (11)
C160.0396 (13)0.0321 (12)0.0381 (12)0.0050 (10)0.0082 (10)0.0048 (10)
Br10.02843 (17)0.03733 (18)0.03321 (18)0.0000.01058 (12)0.000
C90.056 (3)0.148 (12)0.041 (3)0.028 (4)0.003 (2)0.009 (4)
Cl10.0784 (17)0.170 (3)0.129 (2)0.0489 (19)0.0110 (16)0.020 (2)
Cl20.068 (3)0.144 (9)0.063 (3)0.0000.019 (2)0.000
Cl2'0.094 (7)0.234 (17)0.063 (2)0.100 (10)0.024 (3)0.035 (5)
C100.084 (4)0.064 (4)0.056 (3)0.011 (3)0.039 (3)0.015 (3)
Cl30.0666 (8)0.1076 (11)0.0723 (8)0.0000.0278 (6)0.000
Cl40.0721 (10)0.099 (2)0.0690 (9)0.0362 (10)0.0134 (8)0.0046 (9)
Geometric parameters (Å, º) top
N1—C11.329 (2)C11—C121.395 (3)
N1—C21.377 (3)C12—C131.396 (4)
N1—C111.454 (3)C13—C141.373 (4)
C1—N1i1.329 (2)C13—H130.9500
C1—H10.9500C14—C151.371 (4)
C2—C2i1.346 (5)C14—H140.9500
C2—H20.9500C15—C161.393 (4)
C3—C121.515 (3)C15—H150.9500
C3—C51.521 (4)C9—Cl21.691 (10)
C3—C41.525 (4)C9—Cl11.757 (10)
C3—H31.0000C9—Cl2'1.810 (11)
C4—H4A0.9800C9—H9A0.9900
C4—H4B0.9800C9—H9B0.9900
C4—H4C0.9800C9—H9C0.9900
C5—H5A0.9800C9—H9D0.9900
C5—H5B0.9800Cl1—Cl2'i1.51 (3)
C5—H5C0.9800Cl2—C9i1.691 (10)
C6—C71.496 (4)Cl2'—C9i1.280 (11)
C6—C81.503 (4)Cl2'—Cl1i1.51 (3)
C6—C161.514 (3)Cl2'—Cl2'i1.76 (4)
C6—H61.0000C10—Cl41.731 (6)
C7—H7A0.9800C10—Cl31.745 (7)
C7—H7B0.9800C10—H10A0.9900
C7—H7C0.9800C10—H10B0.9900
C8—H8A0.9800Cl3—C10i1.745 (7)
C8—H8B0.9800Cl4—Cl4i0.763 (4)
C8—H8C0.9800Cl4—C10i1.523 (6)
C11—C161.394 (3)
C1—N1—C2108.82 (18)H8A—C8—H8C109.5
C1—N1—C11124.62 (18)H8B—C8—H8C109.5
C2—N1—C11126.56 (18)C16—C11—C12124.2 (2)
N1i—C1—N1108.2 (3)C16—C11—N1118.2 (2)
N1i—C1—H1125.9C12—C11—N1117.7 (2)
N1—C1—H1125.9C11—C12—C13116.2 (2)
C2i—C2—N1107.06 (12)C11—C12—C3123.7 (2)
C2i—C2—H2126.5C13—C12—C3120.1 (2)
N1—C2—H2126.5C14—C13—C12121.2 (3)
C12—C3—C5111.9 (2)C14—C13—H13119.4
C12—C3—C4109.9 (2)C12—C13—H13119.4
C5—C3—C4110.6 (2)C15—C14—C13120.8 (2)
C12—C3—H3108.1C15—C14—H14119.6
C5—C3—H3108.1C13—C14—H14119.6
C4—C3—H3108.1C14—C15—C16121.2 (2)
C3—C4—H4A109.5C14—C15—H15119.4
C3—C4—H4B109.5C16—C15—H15119.4
H4A—C4—H4B109.5C15—C16—C11116.4 (2)
C3—C4—H4C109.5C15—C16—C6121.1 (2)
H4A—C4—H4C109.5C11—C16—C6122.5 (2)
H4B—C4—H4C109.5Cl2—C9—Cl192.2 (4)
C3—C5—H5A109.5Cl2—C9—H9A116.6
C3—C5—H5B109.5Cl1—C9—H9A106.3
H5A—C5—H5B109.5Cl2'—C9—H9A106.3
C3—C5—H5C109.5Cl2—C9—H9B125.7
H5A—C5—H5C109.5Cl1—C9—H9B106.3
H5B—C5—H5C109.5Cl2'—C9—H9B106.3
C7—C6—C8111.2 (3)H9A—C9—H9B106.4
C7—C6—C16111.3 (2)Cl2—C9—H9C113.3
C8—C6—C16112.1 (2)Cl1—C9—H9C113.3
C7—C6—H6107.3Cl2—C9—H9D113.3
C8—C6—H6107.3Cl1—C9—H9D113.3
C16—C6—H6107.3Cl2'—C9—H9D100.2
C6—C7—H7A109.5H9C—C9—H9D110.6
C6—C7—H7B109.5Cl2'i—Cl1—C945.3 (3)
H7A—C7—H7B109.5Cl1i—Cl2'—C9106.2 (9)
C6—C7—H7C109.5Cl4—C10—Cl3111.7 (3)
H7A—C7—H7C109.5Cl4—C10—H10A109.3
H7B—C7—H7C109.5Cl3—C10—H10A109.3
C6—C8—H8A109.5Cl4—C10—H10B109.3
C6—C8—H8B109.5Cl3—C10—H10B109.3
H8A—C8—H8B109.5H10A—C10—H10B107.9
C6—C8—H8C109.5
C2—N1—C1—N1i0.8 (3)C12—C11—C16—C150.9 (4)
C11—N1—C1—N1i179.28 (14)N1—C11—C16—C15178.5 (2)
C1—N1—C2—C2i0.50 (18)C12—C11—C16—C6179.8 (2)
C11—N1—C2—C2i179.60 (16)N1—C11—C16—C60.4 (3)
C1—N1—C11—C1698.5 (3)C7—C6—C16—C1577.5 (4)
C2—N1—C11—C1681.4 (3)C8—C6—C16—C1547.7 (4)
C1—N1—C11—C1281.0 (3)C7—C6—C16—C11101.3 (3)
C2—N1—C11—C1299.1 (3)C8—C6—C16—C11133.5 (3)
C16—C11—C12—C131.2 (4)Cl2—C9—Cl1—Cl2'i2.7 (5)
N1—C11—C12—C13178.1 (2)Cl2'—C9—Cl1—Cl2'i7.6 (4)
C16—C11—C12—C3179.8 (2)Cl1—C9—Cl2—C9i174.0 (2)
N1—C11—C12—C30.8 (4)Cl2'—C9—Cl2—C9i1.6 (6)
C5—C3—C12—C11124.9 (3)Cl2—C9—Cl2'—C9i177.7 (8)
C4—C3—C12—C11111.8 (3)Cl1—C9—Cl2'—C9i173.1 (2)
C5—C3—C12—C1356.2 (4)Cl2—C9—Cl2'—Cl1i175.3 (9)
C4—C3—C12—C1367.1 (3)Cl1—C9—Cl2'—Cl1i166.1 (5)
C11—C12—C13—C140.5 (4)Cl2—C9—Cl2'—Cl2'i2.3 (8)
C3—C12—C13—C14179.5 (3)Cl1—C9—Cl2'—Cl2'i6.9 (2)
C12—C13—C14—C150.6 (5)Cl4—C10—Cl3—C10i50.6 (3)
C13—C14—C15—C160.9 (5)Cl3—C10—Cl4—Cl4i121.8 (4)
C14—C15—C16—C110.2 (4)Cl3—C10—Cl4—C10i58.2 (4)
C14—C15—C16—C6178.7 (3)
Symmetry code: (i) x, y+1/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···Br10.952.593.538 (3)175

Experimental details

Crystal data
Chemical formulaC27H37N2+·Br·2CH2Cl2
Mr639.35
Crystal system, space groupMonoclinic, P21/m
Temperature (K)173
a, b, c (Å)9.1874 (8), 16.5165 (12), 11.030 (1)
β (°) 102.332 (7)
V3)1635.1 (2)
Z2
Radiation typeMo Kα
µ (mm1)1.60
Crystal size (mm)0.52 × 0.28 × 0.24
Data collection
DiffractometerStoe IPDS II two-circle
diffractometer
Absorption correctionMulti-scan
(MULABS; Spek, 2009; Blessing, 1995)
Tmin, Tmax0.489, 0.700
No. of measured, independent and
observed [I > 2σ(I)] reflections
20988, 3200, 2867
Rint0.084
(sin θ/λ)max1)0.610
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.090, 1.03
No. of reflections3200
No. of parameters197
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.43, 0.36

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···Br10.952.593.538 (3)175.1
 

References

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First citationBerger, M., Auner, N. & Bolte, M. (2012). Acta Cryst. E68, o1844.  CSD CrossRef IUCr Journals Google Scholar
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First citationIkhile, M. I. & Bala, M. D. (2010). Acta Cryst. E66, o3121.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationStasch, A., Singh, S., Roesky, H. W., Noltemeyer, M. & Schmidt, H.-G. (2004). Eur. J. Inorg. Chem. pp. 4052–4055.  Web of Science CSD CrossRef Google Scholar
First citationStoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany.  Google Scholar

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