[2,6-Bis(dimethyl-amino-meth-yl)phen-yl]selenium bromide monohydrate.

In the title hydrated molecular salt, C(12)H(19)N(2)Se(+)·Br(-)·H(2)O, the two independent bromide anions lie on a twofold rotation axis. Strong intra-molecular N→Se inter-actions [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 inter-actions [2.56 (6) and 2.63 (7) Å] involving two bromide anions, two cations and two water mol-ecules.

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 = 368.18

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.086

S = 1.09

3093 reflections

167 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.49 e Å−3

Δρmin = −0.53 e Å−3

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 ▶).

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

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

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

C12H19N2Se+·Br−·H2O	F(000) = 1472
Mr = 368.18	Dx = 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

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

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(Fo2) + (0.0287P)2 + 3.8997P] where P = (Fo2 + 2Fc2)/3
3093 reflections	(Δ/σ)max = 0.001
167 parameters	Δρmax = 0.49 e Å−3
0 restraints	Δρmin = −0.53 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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)

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)