4-Formyl-2-nitro-phenyl 4-bromo-benzoate.

In the title compound, C14H8BrNO5, the benzene rings form a dihedral angle of 62.90 (7)°. The central ester group is twisted away from the nitro-substituted and bromo-substituted rings by 71.67 (7) and 8.78 (15)°, respectively. The nitro group forms a dihedral angle of 7.77 (16)° with the benzene ring to which it is attached. In the crystal, mol-ecules are linked by weak C-H⋯O inter-actions, forming C(12) chains which run along [001]. Halogen-halogen inter-actions [Br⋯Br = 3.523 (3) Å] within the chains stabilized by C-H⋯O inter-actions are observed.

Related literature

For medicinal and pharmaceutical properties of nitro­aromatic compounds, see: Jefford & Zaslona (1985 ▶); Bhattacharya et al. (2006 ▶); Benedini et al. (1995 ▶); For similar structures, see: Moreno-Fuquen et al. (2011 ▶, 2013 ▶); Moreno-Fuquen (2011 ▶). For van der Waals radii, see: Bondi (1964 ▶). For halogen–halogen inter­actions see Awwadi et al. (2006 ▶); Hathwar et al. (2010 ▶). For hydrogen bonding, see: Etter (1990 ▶); Nardelli (1995 ▶).

Experimental

Crystal data

C14H8BrNO5

M = 350.12

Monoclinic,

a = 6.5308 (2) Å

b = 8.2253 (2) Å

c = 25.6860 (8) Å

β = 103.1910 (9)°

V = 1343.38 (7) Å3

Z = 4

Mo Kα radiation

μ = 3.08 mm−1

T = 295 K

0.38 × 0.16 × 0.12 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.568, T max = 0.687

16446 measured reflections

2746 independent reflections

2095 reflections with I > 2σ(I)

R int = 0.086

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.113

S = 1.03

2746 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.39 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813010830/hg5309sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813010830/hg5309Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813010830/hg5309Isup3.cml

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

C14H8BrNO5	F(000) = 696
Mr = 350.12	Dx = 1.731 Mg m−3
Monoclinic, P21/c	Melting point: 422(1) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 6.5308 (2) Å	Cell parameters from 3737 reflections
b = 8.2253 (2) Å	θ = 3.0–26.4°
c = 25.6860 (8) Å	µ = 3.08 mm−1
β = 103.1910 (9)°	T = 295 K
V = 1343.38 (7) Å3	Prism, colourless
Z = 4	0.38 × 0.16 × 0.12 mm

Nonius KappaCCD diffractometer	2746 independent reflections
Radiation source: fine-focus sealed tube	2095 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.086
CCD rotation images, thick slices scans	θmax = 26.4°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→6
Tmin = 0.568, Tmax = 0.687	k = −10→9
16446 measured reflections	l = −32→32

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0507P)2 + 0.4984P] where P = (Fo2 + 2Fc2)/3
2746 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.39 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	1.31938 (6)	0.42327 (5)	0.035355 (14)	0.08659 (19)
O1	0.7475 (5)	0.4084 (3)	0.49383 (11)	0.0950 (8)
O2	1.3030 (4)	0.2431 (3)	0.40032 (11)	0.0952 (8)
N1	1.1928 (4)	0.2760 (3)	0.35705 (11)	0.0598 (6)
C1	0.8918 (4)	0.4497 (3)	0.31011 (11)	0.0499 (6)
C2	0.7088 (4)	0.5329 (3)	0.31062 (12)	0.0587 (7)
H2	0.6359	0.5890	0.2790	0.070*
C3	0.6341 (5)	0.5347 (3)	0.35660 (12)	0.0600 (7)
H3	0.5051	0.5909	0.3563	0.072*
C4	0.7415 (4)	0.4571 (3)	0.40263 (11)	0.0542 (6)
C5	0.9260 (4)	0.3742 (3)	0.40244 (10)	0.0509 (6)
H5	1.0040	0.3205	0.4339	0.061*
C6	0.9988 (4)	0.3692 (3)	0.35613 (11)	0.0487 (6)
O3	1.2303 (4)	0.2336 (3)	0.31487 (10)	0.0826 (7)
O4	0.9767 (3)	0.4597 (2)	0.26543 (7)	0.0585 (5)
O5	0.7279 (3)	0.2919 (2)	0.21998 (8)	0.0638 (5)
C7	0.6609 (5)	0.4666 (4)	0.45221 (12)	0.0622 (7)
H7	0.5332	0.5250	0.4518	0.075*
C8	0.8811 (4)	0.3721 (3)	0.22136 (10)	0.0495 (6)
C9	0.9929 (4)	0.3918 (3)	0.17757 (10)	0.0472 (6)
C10	1.1847 (4)	0.4683 (3)	0.18437 (11)	0.0525 (6)
H10	1.2502	0.5140	0.2185	0.063*
C11	1.2847 (4)	0.4808 (3)	0.14219 (12)	0.0575 (7)
H11	1.4190	0.5329	0.1463	0.069*
C12	1.1860 (5)	0.4152 (3)	0.09351 (11)	0.0557 (7)
C13	0.9933 (5)	0.3400 (4)	0.08568 (12)	0.0630 (7)
H13	0.9283	0.2961	0.0512	0.076*
C14	0.8966 (4)	0.3285 (3)	0.12789 (11)	0.0576 (7)
H14	0.7617	0.2769	0.1231	0.069*

	U11	U22	U33	U12	U13	U23
Br1	0.0923 (3)	0.1169 (4)	0.0618 (3)	−0.00649 (19)	0.0410 (2)	0.00527 (18)
O1	0.112 (2)	0.121 (2)	0.0613 (17)	0.0260 (15)	0.0380 (15)	0.0109 (14)
O2	0.0753 (14)	0.133 (2)	0.0756 (17)	0.0367 (14)	0.0142 (13)	0.0138 (15)
N1	0.0586 (13)	0.0586 (13)	0.0649 (16)	0.0002 (10)	0.0197 (12)	−0.0011 (12)
C1	0.0572 (15)	0.0541 (14)	0.0397 (14)	−0.0125 (11)	0.0138 (11)	−0.0027 (11)
C2	0.0602 (16)	0.0662 (16)	0.0492 (16)	0.0020 (13)	0.0113 (13)	0.0072 (13)
C3	0.0592 (16)	0.0650 (17)	0.0578 (18)	0.0083 (13)	0.0171 (14)	0.0017 (14)
C4	0.0619 (16)	0.0555 (15)	0.0495 (16)	0.0002 (12)	0.0217 (13)	−0.0024 (12)
C5	0.0609 (16)	0.0520 (13)	0.0407 (14)	−0.0010 (12)	0.0138 (12)	0.0011 (11)
C6	0.0511 (14)	0.0451 (12)	0.0525 (15)	−0.0026 (11)	0.0168 (12)	−0.0029 (11)
O3	0.0878 (15)	0.0896 (15)	0.0811 (16)	0.0140 (12)	0.0415 (13)	−0.0103 (13)
O4	0.0624 (11)	0.0732 (12)	0.0424 (11)	−0.0174 (9)	0.0169 (9)	−0.0027 (9)
O5	0.0610 (11)	0.0761 (12)	0.0576 (12)	−0.0208 (10)	0.0202 (9)	−0.0045 (9)
C7	0.078 (2)	0.0668 (17)	0.0487 (17)	0.0074 (14)	0.0293 (15)	−0.0008 (14)
C8	0.0528 (15)	0.0511 (13)	0.0439 (14)	−0.0011 (12)	0.0096 (11)	0.0023 (11)
C9	0.0505 (14)	0.0475 (13)	0.0444 (14)	0.0002 (10)	0.0125 (11)	0.0026 (11)
C10	0.0539 (15)	0.0569 (14)	0.0460 (15)	−0.0046 (12)	0.0101 (12)	−0.0037 (12)
C11	0.0564 (15)	0.0607 (16)	0.0581 (18)	−0.0075 (13)	0.0184 (13)	0.0011 (13)
C12	0.0646 (16)	0.0621 (16)	0.0442 (15)	0.0054 (13)	0.0205 (13)	0.0077 (12)
C13	0.0703 (18)	0.0736 (18)	0.0439 (15)	−0.0067 (15)	0.0104 (13)	−0.0018 (13)
C14	0.0554 (15)	0.0690 (17)	0.0479 (16)	−0.0100 (13)	0.0105 (12)	−0.0014 (13)

Br1—C12	1.894 (3)	C5—H5	0.9601
O1—C7	1.190 (4)	O4—C8	1.367 (3)
O2—N1	1.209 (3)	O5—C8	1.192 (3)
N1—O3	1.215 (3)	C7—H7	0.9599
N1—C6	1.476 (3)	C8—C9	1.483 (3)
C1—C2	1.380 (4)	C9—C10	1.377 (4)
C1—O4	1.386 (3)	C9—C14	1.389 (4)
C1—C6	1.395 (4)	C10—C11	1.391 (4)
C2—C3	1.377 (4)	C10—H10	0.9599
C2—H2	0.9599	C11—C12	1.380 (4)
C3—C4	1.385 (4)	C11—H11	0.9600
C3—H3	0.9600	C12—C13	1.375 (4)
C4—C5	1.385 (4)	C13—C14	1.377 (4)
C4—C7	1.487 (4)	C13—H13	0.9601
C5—C6	1.379 (3)	C14—H14	0.9600
O2—N1—O3	123.8 (3)	O1—C7—H7	116.4
O2—N1—C6	117.4 (2)	C4—C7—H7	119.5
O3—N1—C6	118.8 (2)	O5—C8—O4	122.6 (2)
C2—C1—O4	119.3 (2)	O5—C8—C9	126.4 (2)
C2—C1—C6	119.7 (3)	O4—C8—C9	111.1 (2)
O4—C1—C6	120.8 (2)	C10—C9—C14	119.7 (2)
C3—C2—C1	119.4 (3)	C10—C9—C8	123.0 (2)
C3—C2—H2	121.0	C14—C9—C8	117.2 (2)
C1—C2—H2	119.6	C9—C10—C11	120.7 (3)
C2—C3—C4	121.2 (3)	C9—C10—H10	119.8
C2—C3—H3	118.8	C11—C10—H10	119.5
C4—C3—H3	120.0	C12—C11—C10	118.1 (2)
C3—C4—C5	119.7 (3)	C12—C11—H11	120.0
C3—C4—C7	119.9 (3)	C10—C11—H11	121.8
C5—C4—C7	120.5 (3)	C13—C12—C11	122.1 (3)
C6—C5—C4	119.3 (2)	C13—C12—Br1	118.1 (2)
C6—C5—H5	119.5	C11—C12—Br1	119.8 (2)
C4—C5—H5	121.2	C12—C13—C14	119.0 (3)
C5—C6—C1	120.8 (2)	C12—C13—H13	120.1
C5—C6—N1	117.8 (2)	C14—C13—H13	120.9
C1—C6—N1	121.5 (2)	C13—C14—C9	120.3 (3)
C8—O4—C1	117.44 (19)	C13—C14—H14	120.1
O1—C7—C4	124.0 (3)	C9—C14—H14	119.6

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O1i	0.96	2.37	3.254 (4)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O1i	0.96	2.37	3.254 (4)	153

Symmetry code: (i) .