2-Bromo-3-nitro-benzaldehyde.

The title compound, C(7)H(4)BrNO(3), was isolated as a by-product while attempting to prepare a diselenide. There is a close intra-molecular Br⋯O contact [2.984 (2) Å]. The mol-ecules form loosely associated dimers held together by weak inter-molecular Br⋯O inter-actions with the nitro O atoms [Br⋯O = 3.179 (3) Å]. As a result of these inter-actions, there is also a close Br⋯Br inter-molecular contact [3.8714 (6) Å]. In addition, there are weak inter-molecular C-H⋯O inter-actions. The combination of these inter-actions produces sheets which propagate in the (210) and (10) directions perpendicular to c.

Related literature

For the preparation and reactivity of the title compound, see: Rahman & Scrowston (1984 ▶); Sienkowska et al. (2000 ▶); Wirth & Fragale (1997 ▶). For bond-length data, see: Allen (2002 ▶). For intramolecular chalcogen interactions, see: Singh et al. (2009 ▶). For intermolecular Br⋯O interactions, see: Jones & Lozano (2004 ▶); Kruszynski (2007 ▶); Pedireddi et al. (1992 ▶); Xie et al. (2009 ▶).

Experimental

Crystal data

C7H4BrNO3

M = 230.02

Monoclinic,

a = 8.1578 (8) Å

b = 6.3079 (5) Å

c = 15.0537 (11) Å

β = 91.603 (8)°

V = 774.34 (11) Å3

Z = 4

Mo Kα radiation

μ = 5.27 mm−1

T = 296 K

0.27 × 0.18 × 0.09 mm

Data collection

Oxford Diffraction Gemini R diffractometer

Absorption correction: multi-scan (CrysAlisPro; Oxford Diffraction, 2009 ▶) T min = 0.330, T max = 0.649

5208 measured reflections

2120 independent reflections

1308 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.079

S = 0.97

2120 reflections

109 parameters

H-atom parameters constrained

Δρmax = 0.77 e Å−3

Δρmin = −0.45 e Å−3

Data collection: CrysAlisPro (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlisPro; data reduction: CrysAlisPro; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680904104X/om2283sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680904104X/om2283Isup2.hkl

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

C7H4BrNO3	F(000) = 448
Mr = 230.02	Dx = 1.973 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.1578 (8) Å	Cell parameters from 2069 reflections
b = 6.3079 (5) Å	θ = 4.7–30.5°
c = 15.0537 (11) Å	µ = 5.27 mm−1
β = 91.603 (8)°	T = 296 K
V = 774.34 (11) Å3	Rectangular plate, orange
Z = 4	0.27 × 0.18 × 0.09 mm

Oxford Diffraction Gemini R diffractometer	2120 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1308 reflections with I > 2σ(I)
graphite	Rint = 0.031
Detector resolution: 10.5081 pixels mm-1	θmax = 30.6°, θmin = 4.9°
ω scans	h = −11→10
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −8→7
Tmin = 0.330, Tmax = 0.649	l = −21→11
5208 measured reflections

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079	H-atom parameters constrained
S = 0.97	w = 1/[σ2(Fo2) + (0.0388P)2] where P = (Fo2 + 2Fc2)/3
2120 reflections	(Δ/σ)max < 0.001
109 parameters	Δρmax = 0.77 e Å−3
0 restraints	Δρmin = −0.45 e Å−3

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
Br1	0.14664 (4)	0.22483 (5)	0.465488 (18)	0.04777 (13)
O1	0.4218 (3)	0.7906 (3)	0.39513 (14)	0.0541 (5)
O2	−0.0180 (3)	0.1829 (4)	0.63917 (17)	0.0744 (7)
O3	0.1725 (4)	0.1401 (5)	0.73881 (17)	0.0868 (8)
N1	0.1141 (4)	0.2271 (4)	0.67396 (17)	0.0505 (7)
C1	0.3125 (3)	0.6054 (4)	0.51753 (16)	0.0348 (6)
C2	0.2254 (3)	0.4311 (4)	0.54696 (16)	0.0328 (5)
C3	0.2073 (3)	0.4060 (4)	0.63756 (17)	0.0370 (6)
C4	0.2767 (3)	0.5454 (5)	0.69788 (18)	0.0470 (7)
H4	0.2653	0.5227	0.7584	0.056*
C5	0.3621 (4)	0.7169 (5)	0.6692 (2)	0.0508 (8)
H5	0.4088	0.8119	0.7098	0.061*
C6	0.3785 (4)	0.7478 (4)	0.5787 (2)	0.0434 (7)
H6	0.4348	0.8660	0.5587	0.052*
C7	0.3397 (4)	0.6456 (5)	0.42181 (18)	0.0443 (7)
H7	0.2910	0.5545	0.3803	0.053*

	U11	U22	U33	U12	U13	U23
Br1	0.0561 (2)	0.04590 (19)	0.04115 (18)	−0.00979 (14)	−0.00130 (13)	−0.00726 (13)
O1	0.0632 (13)	0.0526 (13)	0.0468 (12)	−0.0092 (11)	0.0069 (10)	0.0147 (10)
O2	0.0641 (16)	0.0862 (18)	0.0735 (17)	−0.0285 (14)	0.0124 (14)	0.0052 (14)
O3	0.119 (2)	0.0817 (19)	0.0591 (15)	−0.0035 (17)	−0.0007 (15)	0.0315 (15)
N1	0.0631 (18)	0.0518 (16)	0.0375 (13)	−0.0010 (13)	0.0145 (13)	0.0043 (12)
C1	0.0361 (14)	0.0354 (14)	0.0329 (13)	0.0038 (11)	0.0010 (11)	−0.0006 (11)
C2	0.0306 (13)	0.0351 (13)	0.0325 (13)	0.0046 (11)	−0.0014 (10)	−0.0021 (11)
C3	0.0363 (14)	0.0407 (14)	0.0341 (14)	0.0034 (12)	0.0039 (11)	0.0007 (11)
C4	0.0520 (18)	0.060 (2)	0.0291 (13)	0.0078 (15)	0.0055 (13)	−0.0049 (13)
C5	0.0549 (19)	0.0558 (18)	0.0413 (16)	−0.0046 (15)	−0.0044 (14)	−0.0159 (14)
C6	0.0449 (17)	0.0392 (17)	0.0460 (16)	−0.0018 (12)	0.0017 (13)	−0.0033 (13)
C7	0.0486 (17)	0.0447 (16)	0.0394 (15)	0.0044 (14)	−0.0053 (13)	0.0003 (13)

Br1—C2	1.889 (2)	C1—C7	1.486 (4)
Br1—O2	2.984 (2)	C2—C3	1.385 (3)
Br1—Br1i	3.8714 (6)	C3—C4	1.375 (4)
O1—C7	1.209 (3)	C4—C5	1.363 (4)
O2—N1	1.217 (4)	C4—H4	0.9300
O2—Br1i	3.179 (3)	C5—C6	1.387 (4)
O3—N1	1.206 (4)	C5—H5	0.9300
N1—C3	1.475 (4)	C6—H6	0.9300
C1—C6	1.384 (4)	C7—H7	0.9300
C1—C2	1.388 (3)
C2—Br1—O2	69.23 (9)	C4—C3—C2	121.6 (2)
C2—Br1—Br1i	122.15 (8)	C4—C3—N1	116.8 (2)
O2—Br1—Br1i	53.36 (5)	C2—C3—N1	121.6 (2)
N1—O2—Br1	86.66 (16)	C5—C4—C3	120.2 (3)
N1—O2—Br1i	132.4 (2)	C5—C4—H4	119.9
Br1—O2—Br1i	77.75 (6)	C3—C4—H4	119.9
O3—N1—O2	124.7 (3)	C4—C5—C6	119.1 (3)
O3—N1—C3	116.9 (3)	C4—C5—H5	120.4
O2—N1—C3	118.4 (3)	C6—C5—H5	120.4
C6—C1—C2	119.6 (2)	C1—C6—C5	121.1 (3)
C6—C1—C7	117.9 (2)	C1—C6—H6	119.5
C2—C1—C7	122.4 (2)	C5—C6—H6	119.5
C3—C2—C1	118.3 (2)	O1—C7—C1	123.4 (3)
C3—C2—Br1	121.12 (19)	O1—C7—H7	118.3
C1—C2—Br1	120.42 (18)	C1—C7—H7	118.3
C2—Br1—O2—N1	−37.66 (19)	Br1—C2—C3—C4	174.2 (2)
Br1i—Br1—O2—N1	134.7 (2)	C1—C2—C3—N1	178.9 (2)
C2—Br1—O2—Br1i	−172.41 (10)	Br1—C2—C3—N1	−5.2 (3)
Br1—O2—N1—O3	−137.5 (3)	O3—N1—C3—C4	−41.7 (4)
Br1i—O2—N1—O3	−67.4 (4)	O2—N1—C3—C4	135.4 (3)
Br1—O2—N1—C3	45.6 (2)	O3—N1—C3—C2	137.7 (3)
Br1i—O2—N1—C3	115.6 (3)	O2—N1—C3—C2	−45.1 (4)
C6—C1—C2—C3	0.2 (4)	C2—C3—C4—C5	1.8 (4)
C7—C1—C2—C3	179.5 (2)	N1—C3—C4—C5	−178.8 (3)
C6—C1—C2—Br1	−175.8 (2)	C3—C4—C5—C6	−0.3 (4)
C7—C1—C2—Br1	3.6 (3)	C2—C1—C6—C5	1.3 (4)
O2—Br1—C2—C3	19.93 (19)	C7—C1—C6—C5	−178.1 (3)
Br1i—Br1—C2—C3	12.7 (2)	C4—C5—C6—C1	−1.3 (5)
O2—Br1—C2—C1	−164.3 (2)	C6—C1—C7—O1	3.1 (4)
Br1i—Br1—C2—C1	−171.45 (16)	C2—C1—C7—O1	−176.3 (3)
C1—C2—C3—C4	−1.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1ii	0.93	2.55	3.354 (4)	145
C7—H7···O3iii	0.93	2.62	3.534 (4)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1i	0.93	2.55	3.354 (4)	145
C7—H7⋯O3ii	0.93	2.62	3.534 (4)	168

Symmetry codes: (i) ; (ii) .