2-Bromo-5-fluoro-benzaldehyde.

In the title compound, C7H4BrFO, the benzaldehyde O atom is found to be trans to the 2-bromo substituent. In the crystal, short Br⋯F inter-actions between the bromine and fluorine substituents are observed at distances of 3.1878 (14), 3.3641 (13) and 3.3675 (14) Å. Offset face-to-face π-stacking inter-actions are also observed for both of the independent mol-ecules in the asymmetric unit running parallel to the crystallographic b axis, characterized by centroid-centroid distances of 3.8699 (2) and 3.8699 (2) Å.

Related literature

For information on the synthesis of 2-bromo-5-fluoro­benzaldehyde, see: Dubost et al. (2011 ▶). For vibrational spectroscopic analysis and ab initio structure calculations on 2-bromo-5-fluoro­benzaldehyde, see: Hiremath & Sundius (2009 ▶). For the use of 2-bromo-5-fluoro­benzaldehyde in organic synthesis of biologically active compounds, see: Chen et al. (2013 ▶). For additional information on halogenated aromatic aldehydes in crystal structures, see: Byrn et al. (1993 ▶); Moorthy et al. (2003 ▶). For information on halogen–halogen inter­actions in crystal structures, see: Pedireddi et al. (1994 ▶).

Experimental

Crystal data

C7H4BrFO

M = 203.01

Monoclinic,

a = 15.3593 (6) Å

b = 3.8699 (2) Å

c = 23.4189 (9) Å

β = 106.330 (1)°

V = 1335.84 (10) Å3

Z = 8

Mo Kα radiation

μ = 6.09 mm−1

T = 125 K

0.36 × 0.16 × 0.03 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.218, T max = 0.838

20203 measured reflections

4080 independent reflections

3468 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.068

S = 1.03

4080 reflections

181 parameters

H-atom parameters constrained

Δρmax = 1.83 e Å−3

Δρmin = −0.82 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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, OLEX2 (Dolomanov et al., 2009 ▶) and Mercury (Macrae et al., 2006 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813018783/jj2171sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813018783/jj2171Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813018783/jj2171Isup3.cml

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

C7H4BrFO	F(000) = 784
Mr = 203.01	Dx = 2.019 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9913 reflections
a = 15.3593 (6) Å	θ = 2.6–30.5°
b = 3.8699 (2) Å	µ = 6.09 mm−1
c = 23.4189 (9) Å	T = 125 K
β = 106.330 (1)°	Plate, colourless
V = 1335.84 (10) Å3	0.36 × 0.16 × 0.03 mm
Z = 8

Bruker APEXII CCD diffractometer	4080 independent reflections
Radiation source: fine-focus sealed tube	3468 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
φ and ω scans	θmax = 30.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −21→21
Tmin = 0.218, Tmax = 0.838	k = −5→5
20203 measured reflections	l = −33→33

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.068	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0289P)2 + 1.4137P] where P = (Fo2 + 2Fc2)/3
4080 reflections	(Δ/σ)max = 0.001
181 parameters	Δρmax = 1.83 e Å−3
0 restraints	Δρmin = −0.82 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	0.080111 (13)	0.22202 (5)	0.216581 (8)	0.01891 (6)
Br2	0.462736 (14)	0.76345 (5)	0.083534 (10)	0.02508 (6)
F1	0.25127 (9)	0.6309 (4)	0.02624 (6)	0.0291 (3)
F2	0.85470 (8)	1.1648 (4)	0.15460 (6)	0.0280 (3)
O1	−0.05661 (10)	0.8333 (4)	0.05688 (7)	0.0262 (3)
O2	0.60148 (11)	1.3284 (5)	0.24807 (7)	0.0319 (4)
C1	−0.01416 (13)	0.6545 (5)	0.09806 (9)	0.0192 (4)
H1A	−0.0436	0.5795	0.1265	0.023*
C2	0.08121 (12)	0.5479 (5)	0.10601 (8)	0.0154 (3)
C3	0.13221 (13)	0.3679 (5)	0.15590 (8)	0.0156 (3)
C4	0.22246 (13)	0.2828 (5)	0.16300 (9)	0.0194 (4)
H4A	0.2564	0.1646	0.1977	0.023*
C5	0.26256 (14)	0.3727 (5)	0.11871 (9)	0.0219 (4)
H5A	0.3241	0.3164	0.1225	0.026*
C6	0.21117 (14)	0.5449 (5)	0.06927 (9)	0.0206 (4)
C7	0.12254 (13)	0.6377 (5)	0.06165 (8)	0.0181 (4)
H7A	0.0898	0.7601	0.0271	0.022*
C8	0.57143 (14)	1.1450 (6)	0.20481 (9)	0.0226 (4)
H8A	0.5118	1.0545	0.1978	0.027*
C9	0.62435 (13)	1.0572 (5)	0.16259 (8)	0.0166 (3)
C10	0.58708 (13)	0.8909 (5)	0.10820 (9)	0.0176 (3)
C11	0.63924 (15)	0.8169 (5)	0.06990 (9)	0.0217 (4)
H11A	0.6125	0.7055	0.0330	0.026*
C12	0.73049 (14)	0.9061 (5)	0.08565 (9)	0.0218 (4)
H12A	0.7673	0.8545	0.0602	0.026*
C13	0.76605 (13)	1.0719 (5)	0.13929 (9)	0.0191 (4)
C14	0.71611 (13)	1.1487 (5)	0.17800 (8)	0.0181 (3)
H14A	0.7435	1.2621	0.2146	0.022*

	U11	U22	U33	U12	U13	U23
Br1	0.02187 (10)	0.01889 (9)	0.01725 (9)	−0.00061 (7)	0.00756 (7)	0.00286 (7)
Br2	0.01723 (10)	0.02099 (11)	0.03344 (12)	−0.00366 (7)	0.00124 (8)	−0.00262 (8)
F1	0.0273 (7)	0.0388 (7)	0.0277 (6)	−0.0023 (6)	0.0182 (5)	0.0033 (6)
F2	0.0148 (6)	0.0395 (7)	0.0314 (7)	−0.0053 (5)	0.0095 (5)	0.0010 (6)
O1	0.0215 (7)	0.0328 (8)	0.0237 (7)	0.0061 (6)	0.0051 (6)	0.0075 (6)
O2	0.0253 (8)	0.0419 (9)	0.0317 (9)	−0.0034 (7)	0.0130 (7)	−0.0137 (7)
C1	0.0164 (8)	0.0208 (9)	0.0212 (9)	−0.0006 (7)	0.0064 (7)	0.0012 (7)
C2	0.0140 (8)	0.0145 (8)	0.0174 (8)	−0.0019 (6)	0.0038 (7)	−0.0007 (6)
C3	0.0175 (8)	0.0134 (8)	0.0168 (8)	−0.0017 (6)	0.0062 (7)	−0.0009 (6)
C4	0.0171 (9)	0.0176 (9)	0.0224 (9)	0.0011 (7)	0.0039 (7)	0.0010 (7)
C5	0.0160 (9)	0.0207 (9)	0.0298 (10)	0.0002 (7)	0.0080 (8)	−0.0013 (8)
C6	0.0222 (10)	0.0216 (9)	0.0219 (9)	−0.0034 (7)	0.0126 (8)	−0.0017 (7)
C7	0.0196 (9)	0.0179 (8)	0.0164 (8)	−0.0032 (7)	0.0044 (7)	−0.0011 (7)
C8	0.0164 (9)	0.0259 (10)	0.0267 (10)	−0.0005 (8)	0.0081 (8)	−0.0012 (8)
C9	0.0152 (8)	0.0151 (8)	0.0206 (9)	0.0006 (6)	0.0066 (7)	0.0014 (7)
C10	0.0145 (8)	0.0144 (8)	0.0221 (9)	0.0000 (6)	0.0023 (7)	0.0016 (7)
C11	0.0260 (10)	0.0190 (9)	0.0190 (9)	0.0016 (8)	0.0047 (8)	0.0007 (7)
C12	0.0250 (10)	0.0224 (9)	0.0212 (9)	0.0026 (8)	0.0115 (8)	0.0024 (7)
C13	0.0143 (9)	0.0214 (9)	0.0221 (9)	−0.0001 (7)	0.0061 (7)	0.0038 (7)
C14	0.0158 (8)	0.0187 (8)	0.0196 (9)	−0.0017 (7)	0.0048 (7)	0.0007 (7)

Br1—C3	1.9021 (18)	C5—C6	1.376 (3)
Br2—C10	1.8985 (19)	C5—H5A	0.9500
Br2—F1	3.1878 (14)	C6—C7	1.370 (3)
F1—C6	1.362 (2)	C7—H7A	0.9500
F2—C13	1.355 (2)	C8—C9	1.485 (3)
F2—Br1i	3.3641 (13)	C8—H8A	0.9500
F2—Br1ii	3.3675 (14)	C9—C10	1.398 (3)
O1—C1	1.217 (3)	C9—C14	1.399 (3)
O2—C8	1.217 (3)	C10—C11	1.390 (3)
C1—C2	1.482 (3)	C11—C12	1.389 (3)
C1—H1A	0.9500	C11—H11A	0.9500
C2—C3	1.396 (3)	C12—C13	1.379 (3)
C2—C7	1.405 (3)	C12—H12A	0.9500
C3—C4	1.389 (3)	C13—C14	1.374 (3)
C4—C5	1.391 (3)	C14—H14A	0.9500
C4—H4A	0.9500
C10—Br2—F1	171.36 (6)	C6—C7—H7A	120.7
C6—F1—Br2	110.32 (11)	C2—C7—H7A	120.7
C13—F2—Br1i	165.26 (12)	O2—C8—C9	122.51 (19)
C13—F2—Br1ii	97.22 (10)	O2—C8—H8A	118.7
Br1i—F2—Br1ii	68.67 (3)	C9—C8—H8A	118.7
O1—C1—C2	123.25 (18)	C10—C9—C14	118.44 (17)
O1—C1—H1A	118.4	C10—C9—C8	123.47 (17)
C2—C1—H1A	118.4	C14—C9—C8	118.09 (17)
C3—C2—C7	118.59 (17)	C11—C10—C9	121.34 (18)
C3—C2—C1	123.09 (16)	C11—C10—Br2	117.59 (15)
C7—C2—C1	118.31 (17)	C9—C10—Br2	121.06 (14)
C4—C3—C2	121.66 (17)	C12—C11—C10	119.94 (19)
C4—C3—Br1	117.11 (14)	C12—C11—H11A	120.0
C2—C3—Br1	121.23 (14)	C10—C11—H11A	120.0
C3—C4—C5	119.19 (18)	C13—C12—C11	117.98 (18)
C3—C4—H4A	120.4	C13—C12—H12A	121.0
C5—C4—H4A	120.4	C11—C12—H12A	121.0
C6—C5—C4	118.62 (18)	F2—C13—C14	118.27 (18)
C6—C5—H5A	120.7	F2—C13—C12	118.38 (17)
C4—C5—H5A	120.7	C14—C13—C12	123.35 (18)
F1—C6—C7	118.63 (18)	C13—C14—C9	118.94 (18)
F1—C6—C5	117.97 (18)	C13—C14—H14A	120.5
C7—C6—C5	123.39 (18)	C9—C14—H14A	120.5
C6—C7—C2	118.54 (18)
O1—C1—C2—C3	174.3 (2)	O2—C8—C9—C14	9.3 (3)
O1—C1—C2—C7	−4.5 (3)	C14—C9—C10—C11	−0.1 (3)
C7—C2—C3—C4	1.3 (3)	C8—C9—C10—C11	179.40 (19)
C1—C2—C3—C4	−177.61 (18)	C14—C9—C10—Br2	−179.19 (14)
C7—C2—C3—Br1	−177.71 (14)	C8—C9—C10—Br2	0.3 (3)
C1—C2—C3—Br1	3.4 (3)	C9—C10—C11—C12	0.5 (3)
C2—C3—C4—C5	−1.4 (3)	Br2—C10—C11—C12	179.70 (15)
Br1—C3—C4—C5	177.64 (15)	C10—C11—C12—C13	−0.9 (3)
C3—C4—C5—C6	0.3 (3)	Br1i—F2—C13—C14	74.6 (5)
Br2—F1—C6—C7	148.75 (15)	Br1ii—F2—C13—C14	58.25 (18)
Br2—F1—C6—C5	−30.4 (2)	Br1i—F2—C13—C12	−105.5 (4)
C4—C5—C6—F1	−179.91 (18)	Br1ii—F2—C13—C12	−121.91 (16)
C4—C5—C6—C7	1.0 (3)	C11—C12—C13—F2	−178.98 (18)
F1—C6—C7—C2	179.81 (17)	C11—C12—C13—C14	0.8 (3)
C5—C6—C7—C2	−1.1 (3)	F2—C13—C14—C9	179.45 (17)
C3—C2—C7—C6	0.0 (3)	C12—C13—C14—C9	−0.4 (3)
C1—C2—C7—C6	178.90 (18)	C10—C9—C14—C13	0.0 (3)
O2—C8—C9—C10	−170.2 (2)	C8—C9—C14—C13	−179.52 (18)