4-Bromo-seleno-anisole.

The title compound, 1-bromo-4-methyl-seleno-benzene, C(7)H(7)BrSe, was prepared by methyl-ation of 4-bromo-seleno-phenolate with methyl iodide, and crystals suitable for structure determination were obtained by sublimation. The mol-ecule is essentially planar; the Se-Me bond is rotated by only 2.59 (19)° out of the least-squares plane of the benzene ring. The most pronounced intermolecular interactions are two hydrogen bonds of the type C-H⋯π, which determine a herring-bone pattern in the crystal packing.

Related literature

For related selenobenzene structures, see: Oddershede et al. (2003 ▶); Sørensen & Stuhr-Hansen (2009 ▶); Stuhr-Hansen et al. (2009 ▶). For the 77Se-NMR spctrum, see: Eggert et al. (1986 ▶). For the melting point, see: Gilow et al. (1968 ▶).

Experimental

Crystal data

C7H7BrSe

M = 250.00

Orthorhombic,

a = 5.8298 (8) Å

b = 7.0671 (11) Å

c = 18.776 (6) Å

V = 773.6 (3) Å3

Z = 4

Cu Kα radiation

μ = 11.86 mm−1

T = 122 K

0.36 × 0.09 × 0.09 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: numerical (DeTitta, 1985 ▶) T min = 0.145, T max = 0.454

5823 measured reflections

1590 independent reflections

1590 reflections with I > 2σ(I)

R int = 0.031

5 standard reflections frequency: 166.7 min intensity decay: 8.7%

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.075

S = 1.15

1590 reflections

83 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.62 e Å−3

Δρmin = −1.30 e Å−3

Absolute structure: Flack (1983 ▶)

Flack parameter: −0.01 (4)

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: DREAR (Blessing, 1987 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680902296X/fj2225sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680902296X/fj2225Isup2.hkl

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

C7H7BrSe	F(000) = 472
Mr = 250.00	Dx = 2.147 Mg m−3
Orthorhombic, Pna21	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2c -2n	Cell parameters from 20 reflections
a = 5.8298 (8) Å	θ = 39.2–40.3°
b = 7.0671 (11) Å	µ = 11.86 mm−1
c = 18.776 (6) Å	T = 122 K
V = 773.6 (3) Å3	Needle, white
Z = 4	0.36 × 0.09 × 0.09 mm

Enraf–Nonius CAD-4 diffractometer	1590 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
graphite	θmax = 74.8°, θmin = 4.7°
ω–2θ scans	h = −7→7
Absorption correction: numerical (DeTitta, 1985)	k = −8→8
Tmin = 0.145, Tmax = 0.454	l = −23→23
5823 measured reflections	5 standard reflections every 166.7 min
1590 independent reflections	intensity decay: 8.7%

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.027	w = 1/[σ2(Fo2) + (0.0537P)2 + 0.4964P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.075	(Δ/σ)max < 0.001
S = 1.15	Δρmax = 0.62 e Å−3
1590 reflections	Δρmin = −1.29 e Å−3
83 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraint	Extinction coefficient: 0.0128 (5)
Primary atom site location: heavy-atom method	Absolute structure: Flack (1983)
Secondary atom site location: difference Fourier map	Flack parameter: −0.01 (4)

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.

	x	y	z	Uiso*/Ueq
Se1	−0.08215 (7)	0.05711 (4)	0.00008 (2)	0.02110 (15)
Br1	0.38155 (8)	−0.04502 (5)	0.317143 (19)	0.02756 (16)
C1	0.0636 (7)	0.0211 (5)	0.0905 (2)	0.0176 (7)
C2	−0.0585 (6)	0.0834 (5)	0.1507 (2)	0.0185 (7)
H2	−0.2055	0.1395	0.1450	0.022*
C3	0.0336 (8)	0.0636 (4)	0.2178 (2)	0.0219 (8)
H3	−0.0478	0.1066	0.2586	0.026*
C4	0.2483 (6)	−0.0207 (5)	0.22490 (18)	0.0184 (7)
C5	0.3691 (6)	−0.0843 (5)	0.1666 (2)	0.0184 (7)
H5	0.5149	−0.1420	0.1727	0.022*
C6	0.2759 (7)	−0.0633 (4)	0.0982 (2)	0.0193 (8)
H6	0.3579	−0.1067	0.0577	0.023*
C7	0.1556 (9)	−0.0397 (6)	−0.0615 (3)	0.0300 (9)
H7A	0.2997	0.0268	−0.0517	0.045*
H7B	0.1117	−0.0195	−0.1113	0.045*
H7C	0.1759	−0.1753	−0.0528	0.045*

	U11	U22	U33	U12	U13	U23
Se1	0.0191 (2)	0.0252 (2)	0.0190 (2)	0.00090 (10)	−0.00294 (17)	0.00115 (15)
Br1	0.0276 (2)	0.0363 (3)	0.0188 (2)	0.00065 (13)	−0.00506 (19)	0.00065 (16)
C1	0.0174 (18)	0.0161 (14)	0.0193 (18)	−0.0014 (12)	−0.0005 (13)	0.0019 (13)
C2	0.0120 (15)	0.0178 (15)	0.026 (2)	0.0030 (12)	0.0026 (13)	−0.0003 (13)
C3	0.022 (2)	0.0201 (16)	0.024 (2)	0.0001 (11)	0.0034 (17)	−0.0019 (12)
C4	0.0186 (19)	0.0202 (16)	0.0166 (17)	−0.0032 (12)	−0.0007 (15)	0.0015 (12)
C5	0.0168 (15)	0.0206 (14)	0.0177 (18)	−0.0018 (12)	0.0009 (13)	−0.0014 (13)
C6	0.0170 (19)	0.0178 (16)	0.0230 (19)	0.0009 (10)	0.0012 (16)	−0.0022 (11)
C7	0.032 (2)	0.039 (2)	0.019 (2)	0.0061 (15)	0.0035 (18)	−0.0038 (14)

Se1—C1	1.916 (4)	C3—H3	0.9500
Se1—C7	1.930 (5)	C4—C5	1.377 (5)
Br1—C4	1.906 (4)	C5—C6	1.401 (6)
C1—C6	1.382 (5)	C5—H5	0.9500
C1—C2	1.406 (5)	C6—H6	0.9500
C2—C3	1.377 (6)	C7—H7A	0.9800
C2—H2	0.9500	C7—H7B	0.9800
C3—C4	1.392 (6)	C7—H7C	0.9800
C1—Se1—C7	99.5 (2)	C4—C5—C6	119.7 (3)
C6—C1—C2	120.3 (4)	C4—C5—H5	120.2
C6—C1—Se1	123.2 (3)	C6—C5—H5	120.2
C2—C1—Se1	116.5 (3)	C1—C6—C5	119.3 (4)
C3—C2—C1	120.4 (4)	C1—C6—H6	120.4
C3—C2—H2	119.8	C5—C6—H6	120.4
C1—C2—H2	119.8	Se1—C7—H7A	109.5
C2—C3—C4	118.8 (4)	Se1—C7—H7B	109.5
C2—C3—H3	120.6	H7A—C7—H7B	109.5
C4—C3—H3	120.6	Se1—C7—H7C	109.5
C5—C4—C3	121.6 (3)	H7A—C7—H7C	109.5
C5—C4—Br1	119.0 (3)	H7B—C7—H7C	109.5
C3—C4—Br1	119.5 (3)
C7—Se1—C1—C6	−3.0 (3)	C2—C3—C4—Br1	178.8 (3)
C7—Se1—C1—C2	177.8 (3)	C3—C4—C5—C6	0.4 (6)
C6—C1—C2—C3	1.0 (5)	Br1—C4—C5—C6	−178.5 (3)
Se1—C1—C2—C3	−179.8 (3)	C2—C1—C6—C5	−0.7 (5)
C1—C2—C3—C4	−0.6 (5)	Se1—C1—C6—C5	−179.8 (3)
C2—C3—C4—C5	−0.1 (5)	C4—C5—C6—C1	0.0 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···C2i	0.95	2.84	3.747 (4)	159
C5—H5···C5ii	0.95	2.83	3.740 (5)	160

Table 1

Selected bond lengths (Å)

Se1—C1	1.916 (4)
Se1—C7	1.930 (5)
Br1—C4	1.906 (4)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯C2i	0.95	2.84	3.747 (4)	159
C5—H5⋯C5ii	0.95	2.83	3.740 (5)	160

Symmetry codes: (i) ; (ii) .