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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 6| June 2013| Pages o941-o942
doi:10.1107/S1600536813013330

4-Hy­dr­oxy-1,2,6-tri­methyl­pyridinium bromide monohydrate

T. Seethalakshmi,a* S. Manivannan,b S. Dhanuskodi,c Daniel E. Lynchd and S. Thamotharane

aDepartment of Physics, Government Arts College (Autonomous), Karur 639 005, India, bCarbon Nanomaterials Laboratory, Department of Physics, National Institute of Technology, Tiruchirappalli 620 015, India, cSchool of Physics, Bharathidasan University, Tiruchirappalli 620 024, India, dFaculty of Health and Life Sciences, Coventry University, Coventry CV1 5FB, England, and eDepartment of Bioinformatics, School of Chemical and Biotechnology, SASTRA University, Thanjavur 613 401, India
*Correspondence e-mail: seetha_b2002@yahoo.com

(Received 7 May 2013; accepted 15 May 2013; online 22 May 2013)

The title salt, C8H12NO+·Br−·H2O, is isomorphous with the chloride analogue [Seethalakshmi et al. (2013). Acta Cryst. E69, o835–o836]. In the solid state, the cations, anions and water mol­ecules are inter­linked by a network of O—H⋯O, O—H⋯Br and C—H⋯Br inter­actions. The water mol­ecule makes two O—H⋯Br hydrogen bonds, generating [010] zigzag chains of alternating water mol­ecules and bromide anions. The cation is involved in two inter­molecular C—H⋯Cl inter­actions in the chloride salt, whereas three inter­molecular C—H⋯Br inter­actions are observed in the title bromide salt. This additional inter­molecular C—H⋯Br inter­action links the adjacent water and bromide zigzag chains via cationic mol­ecules. In addition, weak π–π stacking inter­actions are observed between pyridinium rings [centroid–centroid distance = 3.5664 (13) Å].

Related literature

For related structures, see: Seethalakshmi et al. (2006a[Seethalakshmi, T., Kaliannan, P., Venkatesan, P., Fronczek, F. R. & Thamotharan, S. (2006a). Acta Cryst. E62, o2353-o2355.],b[Seethalakshmi, T., Venkatesan, P., Fronczek, F. R., Kaliannan, P. & Thamotharan, S. (2006b). Acta Cryst. E62, o2560-o2562.],c[Seethalakshmi, T., Venkatesan, P., Fronczek, F. R., Kaliannan, P. & Thamotharan, S. (2006c). Acta Cryst. E62, o3389-o3390.], 2007[Seethalakshmi, T., Manivannan, S., Lynch, D. E., Dhanuskodi, S. & Kaliannan, P. (2007). Acta Cryst. E63, o599-o601.], 2013a[Seethalakshmi, T., Manivannan, S., Dhanuskodi, S., Lynch, D. E. & Thamotharan, S. (2013a). Acta Cryst. E69, o835-o836.],b[Seethalakshmi, T., Venkatesan, P., Nallu, M., Lynch, D. E. & Thamotharan, S. (2013b). Acta Cryst. E69, o884.]). For related compounds, see: Dhanuskodi et al. (2006[Dhanuskodi, S., Manivannan, S. & Kirschbaum, K. (2006). Spectrochim. Acta Part A, 64, 504-511.], 2008[Dhanuskodi, S., Manivannan, S. & Philip, J. (2008). Spectrochim. Acta Part A, 69, 1207-1212.]). For graph-set motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data

  • C8H12NO+·Br−·H2O

  • Mr = 236.11

  • Monoclinic, P 21 /n

  • a = 8.4796 (4) Å

  • b = 8.5874 (6) Å

  • c = 13.8479 (9) Å

  • β = 99.504 (4)°

  • V = 994.53 (11) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 4.10 mm−1

  • T = 120 K

  • 0.30 × 0.30 × 0.25 mm
Data collection

  • Bruker–Nonius 95mm CCD camera on κ-goniostat diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.373, Tmax = 0.427

  • 11830 measured reflections

  • 2277 independent reflections

  • 1888 reflections with I > 2σ(I)

  • Rint = 0.037
Refinement

  • R[F2 > 2σ(F2)] = 0.026

  • wR(F2) = 0.056

  • S = 1.06

  • 2277 reflections

  • 125 parameters

  • 3 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.59 e Å−3

  • Δρmin = −0.34 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1⋯O1Wi 0.83 (2) 1.78 (2) 2.607 (2) 174 (3)
O1W—H1W⋯Br1 0.81 (2) 2.44 (2) 3.2407 (18) 170 (3)
O1W—H2W⋯Br1ii 0.83 (2) 2.43 (2) 3.2527 (18) 168 (3)
C3—H3⋯Br1i 0.95 2.86 3.785 (2) 164
C5—H5⋯Br1iii 0.95 2.90 3.837 (2) 170
C9—H9A⋯Br1iv 0.98 2.91 3.822 (2) 155
Symmetry codes: (i) -x+1, -y, -z+1; (ii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iv) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: COLLECT (Nonius, 1998[Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO; method used to solve structure: isomorphous; program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813013330/tk5224sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813013330/tk5224Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813013330/tk5224Isup3.cml

checkCIF report


Comment top

In continuation of our studies on pyridinium salts (Seethalakshmi et al., 2006a,b,c; 2007; 2013a,b; Dhanuskodi et al., 2006; 2008), we determined crystal and molecular structure of 4-hydroxy-1,2,6-trimethylpyridinium bromide monohydrate, (I). This structure is isomorphous with 4-hydroxy-1,2,6-trimethylpyridinium chloride monohydrate (Seethalakshmi et al. 2013a).

As shown in Fig. 1, the asymmetric unit contains one 4-hydroxy-1,2,6-trimethylpyridinium cation, a bromide anion and a water molecule. The corresponding bond distances and angles of the cation in (I) are comparable with those of related structures (Seethalakshmi et al., 2006a,b,c; 2007; 2013a,b).

The crystal structure of (I) is stabilized by a network of intermolecular O—H···O, O—H···Br and C—H···Br interactions (Table 1, Fig. 2). In (I), the bromide anions and water molecules are interconnected alternately via intermolecular O—H···Br hydrogen bonds. These hydrogen bonds produce a one dimesional zigzag chain which runs parallel to the b axis (Fig. 3). The hydroxy group of the cation acts as a donor for an intermolecular O—H···O hydrogen bond with the water molecule. The way two cation molecules are interlinked is the same as observed in the chloride salt (Seethalakshmi et al., 2013a). The glide related cations are interconnected by an O—H···O—H···Br···H—O···H—O cooperative hydrogen bonding pattern, whereas cation molecules related by translation are interconnected through another type of O—H···O—H···Br···H—O—H···Br···H—O···H—O cooperative hydrogen bonding mode (Fig. 4).

There are three weak intermolecular C—H···Br (C3—H3···Br, C5—H5···Br and C9—H9A···Br) interactions observed in (I), whereas only two C—H···Cl (C3—H3···Cl and C9—H9A···Cl) interactions are found in the crystal structure of chloride salt (Seethalakshmi et al., 2013a). Atom C3 of the cation is involved in a weak C—H···Br intermolecular interaction with bromide anion. As shown in Fig. 4, this weak interaction combines with O—H···O and O—H···Br hydrogen bonds forming a graph-set motif of R23(8) (Bernstein et al., 1995). One of the methyl atoms C9 (via H9A) participates in a weak intermolecular C—H···Br interaction with the bromide anion. Again, this interaction combines with C3—H3···Br and two O—H···Br interactions forming a ring which has a graph-set motif of R24(10). The R23(8) and R24(10) ring motifs are arranged alternately as a helical ribbon which run parallel to the b axis (Fig. 4). Atom C5 of the cation (via H5) is involved in a weak intermolecular C—H···Br interaction. This additional C—H···Br interaction links the adjacent water and bromide zigzag chains via cationic molecules (Fig. 2). In constrast to chloride salt, bromide anion is pentacoordinated by five hydrogen atoms in the crystal structure of (I). The pentacoordination angles in the range of 55–89°. In (I), a weak aromatic π–π stacking interaction is observed between two pyridinium rings related by center of inversion (2 - x, -y, 1 - z) with a centroid-to-centroid distance of 3.5664 (13) Å.

Related literature top

For related structures, see: Seethalakshmi et al. (2006a,b,c, 2007, 2013a,b). For related compounds, see: Dhanuskodi et al. (2006, 2008). For graph-set motifs, see: Bernstein et al. (1995).

Experimental top

The title salt was prepared by dissolving 1-methyl-2,6-dimethyl-4-hydroxypyridine (1.37 g) with hydrobromic acid (2.43 ml) in distilled water (5 ml). The mixture was stirred at room temperature for 7 h and the clear solution was kept for evaporation at 60 °C after filtration. Finally crystalline powder was obtained and dissolved in double distilled water. Single crystals suitable for X-ray diffraction were obtained by slow evaporation.

Refinement top

Since the title salt is isomorphous with its chloride counterpart, it was refined with the coordinates of the cation moiety of chloride salt (Seethalakshmi et al., 2013a). The positions of the Br atom and water molecule were determined from a difference Fourier map and refined anisotropically. The positions of hydroxy H atom and H atoms of water molecule were determined from a difference Fourier map and refined freely along with their isotropic displacement parameters. In the final round of refinement, the O—H bond lengths of the water molecule and hydroxy group are restrained to 0.84 (2) Å. The methyl H atoms were constrained to an ideal geometry (C—H = 0.98 Å), with Uiso(H) = 1.5Ueq(C), but were allowed to rotate freely about the C—C and N—C bonds. The remaining H atoms were placed in geometrically idealized positions (C—H = 0.95 Å), with Uiso(H) = 1.2Ueq(C) and were constrained to ride on their parent atoms.

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: isomorphous method; program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Perspective view of (I), showing the atomic-numbering scheme. The displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A view of the crystal structure of (I), showing the O—H···O, O—H···Br and C—H···Br interactions indicated as dashed lines.
[Figure 3] Fig. 3. One dimensional zigzag chains generated from alternate water and bromide anion interconnected by O—H···Br hydrogen bond which run parallel to the b axis.
[Figure 4] Fig. 4. Stereo view of the arrangement of alternate R23(8) and R24(10) ring motifs.
4-Hydroxy-1,2,6-trimethylpyridinium bromide monohydrate top
Crystal data top
C8H12NO+·Br−·H2OF(000) = 480
Mr = 236.11Dx = 1.577 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2311 reflections
a = 8.4796 (4) Åθ = 1–27.5°
b = 8.5874 (6) ŵ = 4.10 mm−1
c = 13.8479 (9) ÅT = 120 K
β = 99.504 (4)°Block, colourless
V = 994.53 (11) Å30.30 × 0.30 × 0.25 mm
Z = 4
Data collection top
Bruker–Nonius 95mm CCD camera on κ-goniostat
diffractometer		2277 independent reflections
Radiation source: Bruker–Nonius FR591 rotating anode1888 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 2.8°
ϕ and ω scansh = −9→10
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		k = −11→11
Tmin = 0.373, Tmax = 0.427l = −17→17
11830 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.026H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.056 w = 1/[σ2(Fo2) + (0.0179P)2 + 0.9223P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
2277 reflectionsΔρmax = 0.59 e Å−3
125 parametersΔρmin = −0.34 e Å−3
3 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0025 (5)
Crystal data top
C8H12NO+·Br−·H2OV = 994.53 (11) Å3
Mr = 236.11Z = 4
Monoclinic, P21/nMo Kα radiation
a = 8.4796 (4) ŵ = 4.10 mm−1
b = 8.5874 (6) ÅT = 120 K
c = 13.8479 (9) Å0.30 × 0.30 × 0.25 mm
β = 99.504 (4)°
Data collection top
Bruker–Nonius 95mm CCD camera on κ-goniostat
diffractometer		2277 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		1888 reflections with I > 2σ(I)
Tmin = 0.373, Tmax = 0.427Rint = 0.037
11830 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0263 restraints
wR(F2) = 0.056H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.59 e Å−3
2277 reflectionsΔρmin = −0.34 e Å−3
125 parameters
Special details top

Experimental. The minimum and maximum absorption values stated above are those calculated in SHELXL97 from the given crystal dimensions. The ratio of minimum to maximum apparent transmission was determined experimentally as 0.696421.

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*/Ueq
Br10.46272 (3)0.08691 (3)0.252474 (16)0.02160 (9)
O10.8002 (2)−0.29194 (18)0.48421 (13)0.0265 (4)
O1W0.3258 (2)0.3759 (2)0.36438 (13)0.0270 (4)
N10.7983 (2)0.1745 (2)0.42283 (14)0.0185 (4)
C20.7227 (2)0.1241 (2)0.49673 (16)0.0175 (4)
C30.7211 (3)−0.0319 (3)0.51871 (16)0.0185 (5)
H30.6689−0.06700.57030.022*
C40.7960 (3)−0.1390 (3)0.46562 (17)0.0196 (5)
C50.8699 (3)−0.0850 (3)0.38918 (16)0.0199 (5)
H50.9208−0.15650.35190.024*
C60.8691 (2)0.0712 (3)0.36768 (16)0.0190 (5)
C70.9436 (3)0.1302 (3)0.28400 (18)0.0278 (5)
H7A0.86080.17640.23460.042*
H7B0.99450.04360.25480.042*
H7C1.02410.20910.30780.042*
C80.7984 (3)0.3436 (3)0.4015 (2)0.0284 (6)
H8A0.68800.38020.38320.043*
H8B0.85720.36270.34740.043*
H8C0.85010.39990.45980.043*
C90.6442 (3)0.2398 (3)0.55408 (17)0.0236 (5)
H9A0.72520.31020.58890.035*
H9B0.59040.18490.60150.035*
H9C0.56540.30020.50940.035*
H10.756 (3)−0.313 (3)0.5317 (17)0.038 (9)*
H1W0.355 (3)0.309 (3)0.330 (2)0.044 (9)*
H2W0.261 (4)0.432 (3)0.328 (2)0.062 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.02104 (13)0.01973 (12)0.02404 (14)−0.00007 (9)0.00380 (8)0.00019 (10)
O10.0352 (10)0.0132 (8)0.0329 (10)0.0028 (7)0.0108 (8)0.0001 (7)
O1W0.0316 (10)0.0181 (9)0.0307 (10)0.0045 (7)0.0037 (8)0.0019 (8)
N10.0166 (9)0.0138 (9)0.0242 (11)−0.0018 (7)0.0010 (7)−0.0019 (7)
C20.0132 (10)0.0179 (11)0.0201 (12)−0.0013 (8)−0.0015 (8)−0.0028 (9)
C30.0174 (11)0.0195 (11)0.0181 (12)−0.0001 (8)0.0014 (9)−0.0010 (9)
C40.0177 (11)0.0157 (10)0.0240 (12)0.0007 (8)−0.0007 (9)−0.0013 (9)
C50.0177 (11)0.0185 (10)0.0229 (12)0.0004 (9)0.0013 (9)−0.0044 (9)
C60.0143 (10)0.0216 (11)0.0203 (11)−0.0026 (9)0.0002 (8)−0.0021 (9)
C70.0273 (13)0.0305 (13)0.0268 (13)−0.0025 (10)0.0079 (10)0.0022 (10)
C80.0300 (13)0.0153 (11)0.0407 (16)0.0003 (10)0.0081 (11)0.0041 (10)
C90.0254 (12)0.0179 (11)0.0268 (13)0.0035 (9)0.0024 (9)−0.0033 (10)
Geometric parameters (Å, º) top
O1—C41.338 (3)C5—C61.374 (3)
O1—H10.828 (17)C5—H50.9500
O1W—H1W0.813 (17)C6—C71.496 (3)
O1W—H2W0.833 (18)C7—H7A0.9800
N1—C21.365 (3)C7—H7B0.9800
N1—C61.372 (3)C7—H7C0.9800
N1—C81.482 (3)C8—H8A0.9800
C2—C31.374 (3)C8—H8B0.9800
C2—C91.496 (3)C8—H8C0.9800
C3—C41.394 (3)C9—H9A0.9800
C3—H30.9500C9—H9B0.9800
C4—C51.395 (3)C9—H9C0.9800
C4—O1—H1111 (2)C5—C6—C7120.7 (2)
H1W—O1W—H2W107 (3)C6—C7—H7A109.5
C2—N1—C6121.01 (18)C6—C7—H7B109.5
C2—N1—C8118.45 (19)H7A—C7—H7B109.5
C6—N1—C8120.52 (19)C6—C7—H7C109.5
N1—C2—C3119.9 (2)H7A—C7—H7C109.5
N1—C2—C9119.51 (19)H7B—C7—H7C109.5
C3—C2—C9120.6 (2)N1—C8—H8A109.5
C2—C3—C4120.3 (2)N1—C8—H8B109.5
C2—C3—H3119.9H8A—C8—H8B109.5
C4—C3—H3119.9N1—C8—H8C109.5
O1—C4—C3123.1 (2)H8A—C8—H8C109.5
O1—C4—C5118.1 (2)H8B—C8—H8C109.5
C3—C4—C5118.8 (2)C2—C9—H9A109.5
C6—C5—C4120.1 (2)C2—C9—H9B109.5
C6—C5—H5119.9H9A—C9—H9B109.5
C4—C5—H5119.9C2—C9—H9C109.5
N1—C6—C5119.8 (2)H9A—C9—H9C109.5
N1—C6—C7119.5 (2)H9B—C9—H9C109.5
C6—N1—C2—C32.1 (3)O1—C4—C5—C6−179.7 (2)
C8—N1—C2—C3−179.6 (2)C3—C4—C5—C60.4 (3)
C6—N1—C2—C9−178.86 (19)C2—N1—C6—C5−2.6 (3)
C8—N1—C2—C9−0.6 (3)C8—N1—C6—C5179.2 (2)
N1—C2—C3—C4−0.3 (3)C2—N1—C6—C7176.9 (2)
C9—C2—C3—C4−179.33 (19)C8—N1—C6—C7−1.4 (3)
C2—C3—C4—O1179.2 (2)C4—C5—C6—N11.3 (3)
C2—C3—C4—C5−1.0 (3)C4—C5—C6—C7−178.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O1Wi0.83 (2)1.78 (2)2.607 (2)174 (3)
O1W—H1W···Br10.81 (2)2.44 (2)3.2407 (18)170 (3)
O1W—H2W···Br1ii0.83 (2)2.43 (2)3.2527 (18)168 (3)
C3—H3···Br1i0.952.863.785 (2)164
C5—H5···Br1iii0.952.903.837 (2)170
C9—H9A···Br1iv0.982.913.822 (2)155
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1/2, y+1/2, −z+1/2; (iii) −x+3/2, y−1/2, −z+1/2; (iv) x+1/2, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC8H12NO+·Br−·H2O
Mr236.11
Crystal system, space groupMonoclinic, P21/n
Temperature (K)120
a, b, c (Å)8.4796 (4), 8.5874 (6), 13.8479 (9)
β (°) 99.504 (4)
V (Å3)994.53 (11)
Z4
Radiation typeMo Kα
µ (mm−1)4.10
Crystal size (mm)0.30 × 0.30 × 0.25
Data collection
DiffractometerBruker–Nonius 95mm CCD camera on κ-goniostat
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.373, 0.427
No. of measured, independent and
observed [I > 2σ(I)] reflections		11830, 2277, 1888
Rint0.037
(sin θ/λ)max (Å−1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.026, 0.056, 1.06
No. of reflections2277
No. of parameters125
No. of restraints3
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.59, −0.34

Computer programs: COLLECT (Nonius, 1998), DENZO (Otwinowski & Minor, 1997), isomorphous method, SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O1Wi0.828 (17)1.783 (18)2.607 (2)174 (3)
O1W—H1W···Br10.813 (17)2.436 (18)3.2407 (18)170 (3)
O1W—H2W···Br1ii0.833 (18)2.433 (19)3.2527 (18)168 (3)
C3—H3···Br1i0.952.863.785 (2)164
C5—H5···Br1iii0.952.903.837 (2)170
C9—H9A···Br1iv0.982.913.822 (2)155
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1/2, y+1/2, −z+1/2; (iii) −x+3/2, y−1/2, −z+1/2; (iv) x+1/2, −y+1/2, z+1/2.
 

Acknowledgements

The authors thank the EPSRC National Crystallography Service (University of Southampton, UK) for the X-ray data collection. ST thanks the management of SASTRA University for their encouragement.

References

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ISSN: 2056-9890
Volume 69| Part 6| June 2013| Pages o941-o942
doi:10.1107/S1600536813013330
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