[2,6-Bis(dimethyl­amino­meth­yl)phen­yl]selenium bromide monohydrate

Varga, R.A.; Kulcsar, M.; Silvestru, A.

doi:10.1107/S1600536810008019

organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page o771

doi:10.1107/S1600536810008019

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[2,6-Bis(dimethylaminomethyl)phenyl]selenium bromide monohydrate

Richard A. Varga,^a ^* Monica Kulcsar ^b and Anca Silvestru ^a

^aFaculty of Chemistry and Chemical Engineering, Babes-Bolyai University, Arany Janos Str. no. 11, RO-400028, Cluj Napoca, Romania, and ^bDepartamento de Química Inorgánica, Instituto de Ciencia de, Materiales de Aragón, Universidad de Zaragoza–CSIC, E-50009 Zaragoza, Spain
^*Correspondence e-mail: richy@chem.ubbcluj.ro

(Received 4 February 2010; accepted 2 March 2010; online 6 March 2010)

In the title hydrated molecular salt, C₁₂H₁₉N₂Se⁺·Br⁻·H₂O, the two independent bromide anions lie on a twofold rotation axis. Strong intramolecular N→Se interactions [2.185 (3) and 2.181 (3) Å] are established by both N atoms of the organic group in the cation, in trans positions to each other, with an N—Se—N angle of 161.6 (1)°, resulting in a T-shaped (C,N,N′)Se core. In the crystal, dimeric associations are formed by Br⋯Se [3.662 (2) Å] and Br⋯H interactions [2.56 (6) and 2.63 (7) Å] involving two bromide anions, two cations and two water molecules.

Related literature

For related selenium and tellurium compounds, see: Drake et al. (2001a ,b ); Deleanu et al. (2002 ); Kulcsar et al. (2005 , 2007 ); Beleaga et al. (2009 ); Fujihara et al. (1995 ). For van der Waals radii, see: Emsley (1994 ).

Experimental

Crystal data

C₁₂H₁₉N₂Se⁺·Br⁻·H₂O
M_r = 368.18
Monoclinic, C 2/c
a = 15.1494 (14) Å
b = 11.3182 (10) Å
c = 18.8083 (17) Å
β = 110.475 (2)°
V = 3021.2 (5) Å³
Z = 8
Mo Kα radiation
μ = 5.12 mm⁻¹
T = 297 K
0.31 × 0.29 × 0.09 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.300, T_max = 0.656
11856 measured reflections
3093 independent reflections
2696 reflections with I > 2/s(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.086
S = 1.09
3093 reflections
167 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.53 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯Br2	0.78 (6)	2.56 (6)	3.340 (5)	175 (5)
O1—H2⋯Br1	0.78 (6)	2.63 (7)	3.406 (5)	176 (7)

Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus (Bruker, 2001 ); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND 3 (Brandenburg & Putz, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810008019/dn2538sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810008019/dn2538Isup2.hkl

checkCIF report

Comment top

In the last years our interest was focused on the synthesis, structural characterization and chemical reactivity of some new hypervalent organoselenium and organotellurium derivatives containing aryl groups with pendant arms, e.g. 2-(Me₂NCH₂)C₆H₄, 2-[O(CH₂CH₂)₂NCH₂]C₆H₄ and 2-[MeN(CH₂CH₂)₂NCH₂]C₆H₄ (Drake et al., 2001a,b, Deleanu et al.,2002, Kulcsar et al., 2005, 2007, Beleaga et al., 2009).

The crystal of the title compound contains a mixture of [{2,6-(Me₂NCH₂)₂C₆H₃}Se]⁺ cations and [Br]^- anions and crystallizes with a water molecule. The two independent bromine anions lie on a two-fold rotation axis. Both pendant arms of the organic group attached to selenium establish strong intramolecular N→Se interactions [Se—N1 = 2.185 (3) Å, Se1—N2 = 2.181 (3) Å], trans one to the other [N1—Se1—N2 = 161.6 (1)°], thus resulting in the increase of the coordination number at Se to three (Fig. 1). The Se—N distances are of the same magnitude as found in the cation of [{2,6-(Me₂NCH₂)₂C₆H₃}Se]⁺[PF₆]^- [Se1—N1 = 2.180 Å; Se1—N2 = 2.154 Å] (Fujihara et al., 1995). This results in a distorted T-shaped (C,N,N')Se core [C1—Se1—N1 = 80.5 (1)°, C1—Se1—N2 = 81.2 (1)°], the distortion being mainly due to the constraints imposed by the two SeC₃N five-membered chelate rings.

An unusual dimer association is formed between two cations, two bromine atoms and two water molecules (Fig. 2). The Br2 atom is involved in bridging two selenium atoms and the interatomic Se1—Br2 distances [3.662 (2) Å] are much longer than the sum of the corresponding covalent radii [Σr_cov(Se,Br) ca. 2.31 Å], but shorter than the sum of the van der Waals radii [Σr_vdW(Se,Br) ca. 3.95 Å] (Emsley, 1994), consistent with an electrostatic anion-cation interaction. This interaction is directed trans to the selenium-carbon bond in the cation [C1—Se1—Br2 = 154.4 (1)°], thus resulting in a distorted square-planar environment around the chalcogen atom. The water molecules bridge the Br1 and Br2 anions through Br···H hydrogen bonding [Br1···H1 = 2.56 (6) Å, Br2···H2 = 2.63 (7) Å].

Related literature top

For related selenium and tellurium compounds, see: Drake et al. (2001a,b); Deleanu et al. (2002); Kulcsar et al. (2005, 2007); Beleaga et al. (2009); Fujihara et al. (1995). For van der Waals radii, see: Emsley (1994).

Experimental top

[2,6-(Me₂NCH₂)₂C₆H₃]SeBr was obtained by oxidizing [2,6-(Me₂NCH₂)₂C₆H₃]₂Se₂with elemental bromine.

The attempt to grow crystals of [2,6-(Me₂NCH₂)₂C₆H₃]SeBr from a methylene dichloride / n-hexane mixture (1:5, v/v) in open atmosphere led to the isolation of [2,6-(Me₂NCH₂)₂C₆H₃]SeBr.H₂O.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus (Bruker, 2000); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND 3 (Brandenburg & Putz, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. : View of title compound showing the atom-numbering scheme at 30% probability thermal ellipsoids.
	Fig. 2. : Intra- and intermolecular interactions in the title compound (dashed lines; only H atoms involved in interactions are shown) [symmetry code: (i) = 1-x, y, 1.5-z].

[2,6-Bis(dimethylaminomethyl)phenyl]selenium bromide monohydrate top

Crystal data top

C₁₂H₁₉N₂Se⁺·Br⁻·H₂O	F(000) = 1472
M_r = 368.18	D_x = 1.619 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3226 reflections
a = 15.1494 (14) Å	θ = 2.3–25.2°
b = 11.3182 (10) Å	µ = 5.12 mm⁻¹
c = 18.8083 (17) Å	T = 297 K
β = 110.475 (2)°	Block, colourless
V = 3021.2 (5) Å³	0.31 × 0.29 × 0.09 mm
Z = 8

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3093 independent reflections
Radiation source: fine-focus sealed tube	2696 reflections with I > 2/s(I)
Graphite monochromator	R_int = 0.050
phi and ω scans	θ_max = 26.4°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −18→18
T_min = 0.300, T_max = 0.656	k = −14→14
11856 measured reflections	l = −23→23

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.0287P)² + 3.8997P] where P = (F_o² + 2F_c²)/3
3093 reflections	(Δ/σ)_max = 0.001
167 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.53 e Å⁻³

Crystal data top

C₁₂H₁₉N₂Se⁺·Br⁻·H₂O	V = 3021.2 (5) Å³
M_r = 368.18	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 15.1494 (14) Å	µ = 5.12 mm⁻¹
b = 11.3182 (10) Å	T = 297 K
c = 18.8083 (17) Å	0.31 × 0.29 × 0.09 mm
β = 110.475 (2)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3093 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2696 reflections with I > 2/s(I)
T_min = 0.300, T_max = 0.656	R_int = 0.050
11856 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.49 e Å⁻³
3093 reflections	Δρ_min = −0.53 e Å⁻³
167 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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

	x	y	z	U_iso*/U_eq
Br1	0.5000	0.26510 (5)	0.7500	0.05461 (17)
Br2	0.5000	0.73811 (6)	0.7500	0.0747 (2)
C1	0.3337 (2)	0.9300 (3)	0.93573 (18)	0.0319 (7)
C2	0.3774 (2)	0.9329 (3)	1.01348 (18)	0.0372 (7)
C6	0.2603 (2)	1.0046 (3)	0.89677 (19)	0.0346 (7)
C10	0.2169 (2)	0.9828 (3)	0.81308 (19)	0.0408 (8)
H10A	0.1640	0.9290	0.8028	0.049*
H10B	0.1939	1.0565	0.7868	0.049*
C7	0.4589 (3)	0.8503 (3)	1.04538 (19)	0.0444 (8)
H7A	0.5173	0.8906	1.0505	0.053*
H7B	0.4622	0.8232	1.0952	0.053*
C8	0.3799 (3)	0.6604 (3)	1.0050 (3)	0.0572 (11)
H8A	0.4077	0.6257	1.0544	0.086*
H8B	0.3677	0.5999	0.9670	0.086*
H8C	0.3218	0.6984	1.0014	0.086*
C9	0.5358 (3)	0.6906 (4)	0.9999 (2)	0.0561 (10)
H9A	0.5780	0.7482	0.9919	0.084*
H9B	0.5246	0.6294	0.9624	0.084*
H9C	0.5635	0.6570	1.0496	0.084*
C12	0.3495 (3)	1.0235 (3)	0.7709 (2)	0.0495 (9)
H12A	0.4006	0.9872	0.7599	0.074*
H12B	0.3744	1.0733	0.8147	0.074*
H12C	0.3126	1.0702	0.7282	0.074*
C11	0.2469 (3)	0.8570 (4)	0.7181 (2)	0.0525 (9)
H11A	0.2098	0.9056	0.6767	0.079*
H11B	0.2073	0.7982	0.7286	0.079*
H11C	0.2957	0.8189	0.7050	0.079*
C5	0.2301 (3)	1.0860 (3)	0.9381 (2)	0.0454 (9)
H5	0.1810	1.1374	0.9134	0.054*
C4	0.2730 (3)	1.0911 (3)	1.0160 (2)	0.0505 (9)
H4	0.2525	1.1462	1.0434	0.061*
C3	0.3460 (3)	1.0155 (3)	1.0540 (2)	0.0473 (9)
H3	0.3740	1.0198	1.1065	0.057*
N1	0.4453 (2)	0.7484 (2)	0.99307 (16)	0.0385 (7)
N2	0.28962 (19)	0.9310 (2)	0.78604 (15)	0.0372 (6)
O1	0.4714 (3)	0.5053 (4)	0.8489 (2)	0.0793 (11)
Se1	0.37778 (2)	0.82185 (3)	0.879443 (18)	0.03542 (12)
H1	0.480 (4)	0.562 (5)	0.828 (3)	0.09 (2)*
H2	0.475 (5)	0.451 (6)	0.825 (4)	0.12 (3)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0623 (4)	0.0495 (3)	0.0552 (4)	0.000	0.0246 (3)	0.000
Br2	0.0914 (5)	0.0596 (4)	0.0986 (6)	0.000	0.0651 (5)	0.000
C1	0.0345 (17)	0.0321 (16)	0.0323 (17)	−0.0077 (13)	0.0157 (14)	−0.0033 (13)
C2	0.0410 (19)	0.0415 (18)	0.0301 (18)	−0.0085 (15)	0.0139 (15)	0.0012 (14)
C6	0.0337 (17)	0.0329 (16)	0.0367 (18)	−0.0046 (13)	0.0117 (14)	−0.0018 (13)
C10	0.0355 (18)	0.0434 (19)	0.0379 (19)	0.0018 (15)	0.0057 (15)	0.0008 (15)
C7	0.043 (2)	0.057 (2)	0.0302 (18)	−0.0040 (17)	0.0092 (15)	0.0064 (16)
C8	0.045 (2)	0.050 (2)	0.073 (3)	−0.0058 (17)	0.016 (2)	0.021 (2)
C9	0.040 (2)	0.065 (3)	0.061 (3)	0.0149 (19)	0.0143 (19)	0.014 (2)
C12	0.056 (2)	0.053 (2)	0.040 (2)	−0.0079 (18)	0.0165 (18)	0.0080 (17)
C11	0.058 (2)	0.055 (2)	0.036 (2)	−0.0003 (19)	0.0076 (18)	−0.0115 (17)
C5	0.047 (2)	0.0364 (18)	0.056 (2)	0.0009 (16)	0.0221 (18)	−0.0025 (16)
C4	0.063 (2)	0.043 (2)	0.055 (2)	−0.0016 (19)	0.033 (2)	−0.0114 (18)
C3	0.060 (2)	0.054 (2)	0.0317 (19)	−0.0089 (19)	0.0210 (18)	−0.0050 (16)
N1	0.0319 (15)	0.0426 (16)	0.0395 (16)	0.0017 (12)	0.0108 (13)	0.0081 (12)
N2	0.0412 (16)	0.0396 (15)	0.0273 (14)	−0.0040 (12)	0.0076 (12)	−0.0005 (12)
O1	0.106 (3)	0.077 (3)	0.046 (2)	−0.007 (2)	0.0145 (19)	0.0004 (19)
Se1	0.03654 (19)	0.03788 (19)	0.03126 (19)	0.00273 (14)	0.01113 (14)	−0.00128 (14)

Geometric parameters (Å, º) top

C1—C2	1.379 (4)	C9—H9B	0.9600
C1—C6	1.384 (5)	C9—H9C	0.9600
C1—Se1	1.887 (3)	C12—N2	1.478 (4)
C2—C3	1.391 (5)	C12—H12A	0.9600
C2—C7	1.497 (5)	C12—H12B	0.9600
C6—C5	1.382 (5)	C12—H12C	0.9600
C6—C10	1.499 (5)	C11—N2	1.474 (4)
C10—N2	1.487 (4)	C11—H11A	0.9600
C10—H10A	0.9700	C11—H11B	0.9600
C10—H10B	0.9700	C11—H11C	0.9600
C7—N1	1.483 (5)	C5—C4	1.381 (5)
C7—H7A	0.9700	C5—H5	0.9300
C7—H7B	0.9700	C4—C3	1.383 (5)
C8—N1	1.476 (4)	C4—H4	0.9300
C8—H8A	0.9600	C3—H3	0.9300
C8—H8B	0.9600	N1—Se1	2.185 (3)
C8—H8C	0.9600	N2—Se1	2.180 (3)
C9—N1	1.484 (5)	O1—H1	0.78 (6)
C9—H9A	0.9600	O1—H2	0.78 (6)

C2—C1—C6	123.1 (3)	H12A—C12—H12B	109.5
C2—C1—Se1	118.5 (2)	N2—C12—H12C	109.5
C6—C1—Se1	118.4 (2)	H12A—C12—H12C	109.5
C1—C2—C3	117.9 (3)	H12B—C12—H12C	109.5
C1—C2—C7	115.7 (3)	N2—C11—H11A	109.5
C3—C2—C7	126.3 (3)	N2—C11—H11B	109.5
C5—C6—C1	118.1 (3)	H11A—C11—H11B	109.5
C5—C6—C10	126.1 (3)	N2—C11—H11C	109.5
C1—C6—C10	115.6 (3)	H11A—C11—H11C	109.5
N2—C10—C6	108.6 (3)	H11B—C11—H11C	109.5
N2—C10—H10A	110.0	C4—C5—C6	119.9 (3)
C6—C10—H10A	110.0	C4—C5—H5	120.1
N2—C10—H10B	110.0	C6—C5—H5	120.1
C6—C10—H10B	110.0	C5—C4—C3	121.2 (3)
H10A—C10—H10B	108.4	C5—C4—H4	119.4
N1—C7—C2	108.4 (3)	C3—C4—H4	119.4
N1—C7—H7A	110.0	C4—C3—C2	119.8 (3)
C2—C7—H7A	110.0	C4—C3—H3	120.1
N1—C7—H7B	110.0	C2—C3—H3	120.1
C2—C7—H7B	110.0	C8—N1—C7	111.6 (3)
H7A—C7—H7B	108.4	C8—N1—C9	109.8 (3)
N1—C8—H8A	109.5	C7—N1—C9	112.1 (3)
N1—C8—H8B	109.5	C8—N1—Se1	107.2 (2)
H8A—C8—H8B	109.5	C7—N1—Se1	105.19 (19)
N1—C8—H8C	109.5	C9—N1—Se1	110.7 (2)
H8A—C8—H8C	109.5	C11—N2—C12	110.4 (3)
H8B—C8—H8C	109.5	C11—N2—C10	111.5 (3)
N1—C9—H9A	109.5	C12—N2—C10	111.4 (3)
N1—C9—H9B	109.5	C11—N2—Se1	109.6 (2)
H9A—C9—H9B	109.5	C12—N2—Se1	108.2 (2)
N1—C9—H9C	109.5	C10—N2—Se1	105.46 (19)
H9A—C9—H9C	109.5	H1—O1—H2	107 (6)
H9B—C9—H9C	109.5	C1—Se1—N2	81.21 (12)
N2—C12—H12A	109.5	C1—Se1—N1	80.47 (12)
N2—C12—H12B	109.5	N2—Se1—N1	161.56 (11)

C6—C1—C2—C3	−0.4 (5)	C2—C7—N1—Se1	34.9 (3)
Se1—C1—C2—C3	178.1 (2)	C6—C10—N2—C11	152.9 (3)
C6—C1—C2—C7	−176.8 (3)	C6—C10—N2—C12	−83.3 (3)
Se1—C1—C2—C7	1.8 (4)	C6—C10—N2—Se1	33.9 (3)
C2—C1—C6—C5	0.4 (5)	C2—C1—Se1—N2	−166.9 (3)
Se1—C1—C6—C5	−178.1 (2)	C6—C1—Se1—N2	11.7 (2)
C2—C1—C6—C10	−175.7 (3)	C2—C1—Se1—N1	15.2 (2)
Se1—C1—C6—C10	5.7 (4)	C6—C1—Se1—N1	−166.2 (3)
C5—C6—C10—N2	155.8 (3)	C11—N2—Se1—C1	−146.0 (3)
C1—C6—C10—N2	−28.4 (4)	C12—N2—Se1—C1	93.5 (2)
C1—C2—C7—N1	−26.9 (4)	C10—N2—Se1—C1	−25.8 (2)
C3—C2—C7—N1	157.1 (3)	C11—N2—Se1—N1	−139.3 (3)
C1—C6—C5—C4	−0.1 (5)	C12—N2—Se1—N1	100.2 (4)
C10—C6—C5—C4	175.6 (3)	C10—N2—Se1—N1	−19.1 (4)
C6—C5—C4—C3	−0.2 (6)	C8—N1—Se1—C1	90.8 (2)
C5—C4—C3—C2	0.2 (6)	C7—N1—Se1—C1	−28.1 (2)
C1—C2—C3—C4	0.1 (5)	C9—N1—Se1—C1	−149.4 (3)
C7—C2—C3—C4	176.0 (3)	C8—N1—Se1—N2	84.2 (4)
C2—C7—N1—C8	−81.0 (3)	C7—N1—Se1—N2	−34.8 (4)
C2—C7—N1—C9	155.3 (3)	C9—N1—Se1—N2	−156.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···Br2	0.78 (6)	2.56 (6)	3.340 (5)	175 (5)
O1—H2···Br1	0.78 (6)	2.63 (7)	3.406 (5)	176 (7)

Experimental details

Crystal data
Chemical formula	C₁₂H₁₉N₂Se⁺·Br⁻·H₂O
M_r	368.18
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	297
a, b, c (Å)	15.1494 (14), 11.3182 (10), 18.8083 (17)
β (°)	110.475 (2)
V (Å³)	3021.2 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	5.12
Crystal size (mm)	0.31 × 0.29 × 0.09

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.300, 0.656
No. of measured, independent and observed [I > 2/s(I)] reflections	11856, 3093, 2696
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.086, 1.09
No. of reflections	3093
No. of parameters	167
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.53

Computer programs: SMART (Bruker, 2000), SAINT-Plus (Bruker, 2000), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND 3 (Brandenburg & Putz, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···Br2	0.78 (6)	2.56 (6)	3.340 (5)	175 (5)
O1—H2···Br1	0.78 (6)	2.63 (7)	3.406 (5)	176 (7)

Acknowledgements

This work was supported by the Romanian Ministery of Education and Research (PNII Program, grant 2404/2008). We also thank the National Center for X-ray Diffraction, Cluj-Napoca, for the structure determination.

References

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