4-Nitro-phenyl 4-bromo-benzoate.

In the crystal structure of the title compound, C(13)H(8)BrNO(4), mol-ecules are linked into chains along [101] by weak C-H⋯O hydrogen bonds and Br⋯O contacts [3.140 (4) Å]. The planes of the nitrated and brominated aryl rings form a dihedral angle of 64.98 (10)°, indicating a twist in the mol-ecule.

Related literature

For background to the applications of aromatic esters containing nitro groups, see: Jefford & Zaslona (1985 ▶). For mol­ecular and supra­molecular structures of nitroaryl compounds, see: Wardell et al. (2005 ▶); Jefford et al., (1986 ▶). For halogen bonding, see: Politzer et al. (2010 ▶); Ritter (2009 ▶). For hydrogen bonding, see: Nardelli (1995 ▶) and for hydrogen-bond graph-set motifs, see: Etter (1990 ▶).

Experimental

Crystal data

C13H8BrNO4

M = 322.11

Monoclinic,

a = 8.8177 (4) Å

b = 9.5279 (5) Å

c = 14.9394 (5) Å

β = 99.024 (3)°

V = 1239.59 (10) Å3

Z = 4

Mo Kα radiation

μ = 3.33 mm−1

T = 293 K

0.55 × 0.31 × 0.23 mm

Data collection

Bruker–Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.250, T max = 0.361

9341 measured reflections

2648 independent reflections

1918 reflections with I > 2σ(I)

R int = 0.070

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.137

S = 1.02

2648 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.80 e Å−3

Δρmin = −0.68 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); 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, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811043923/hg5114sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811043923/hg5114Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811043923/hg5114Isup3.cml

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

C13H8BrNO4	F(000) = 640
Mr = 322.11	Dx = 1.726 Mg m−3
Monoclinic, P21/c	Melting point: 431(1) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.8177 (4) Å	Cell parameters from 5487 reflections
b = 9.5279 (5) Å	θ = 2.9–27.1°
c = 14.9394 (5) Å	µ = 3.33 mm−1
β = 99.024 (3)°	T = 293 K
V = 1239.59 (10) Å3	Block, pale-yellow
Z = 4	0.55 × 0.31 × 0.23 mm

Bruker–Nonius KappaCCD diffractometer	2648 independent reflections
Radiation source: fine-focus sealed tube	1918 reflections with I > 2σ(I)
graphite	Rint = 0.070
ω scans	θmax = 27.1°, θmin = 3.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→11
Tmin = 0.250, Tmax = 0.361	k = −11→11
9341 measured reflections	l = −19→16

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0723P)2 + 0.6227P] where P = (Fo2 + 2Fc2)/3
2648 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.80 e Å−3
0 restraints	Δρmin = −0.68 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
Br	1.07826 (4)	0.25892 (4)	1.01950 (2)	0.0659 (2)
O2	0.6701 (3)	0.1952 (3)	0.59586 (16)	0.0569 (6)
C1	0.9755 (4)	0.2726 (4)	0.8984 (2)	0.0507 (8)
O1	0.7563 (3)	0.4159 (3)	0.58276 (16)	0.0606 (6)
C4	0.8266 (4)	0.2946 (3)	0.7227 (2)	0.0457 (7)
C8	0.5953 (4)	0.1968 (4)	0.5064 (2)	0.0480 (7)
C11	0.4518 (4)	0.1846 (4)	0.3321 (2)	0.0504 (8)
C10	0.5615 (4)	0.0861 (4)	0.3623 (2)	0.0552 (8)
H10	0.5859	0.0161	0.3235	0.066*
N1	0.3778 (5)	0.1834 (4)	0.2373 (2)	0.0694 (9)
C7	0.7503 (4)	0.3138 (4)	0.6281 (2)	0.0485 (7)
C5	0.9242 (4)	0.4006 (4)	0.7604 (3)	0.0594 (9)
H5	0.9388	0.4796	0.7261	0.071*
C2	0.8757 (4)	0.1668 (4)	0.8629 (2)	0.0527 (8)
H2	0.8587	0.0893	0.8978	0.063*
C3	0.8023 (4)	0.1793 (3)	0.7748 (2)	0.0499 (8)
H3	0.7354	0.1090	0.7499	0.060*
C6	0.9997 (5)	0.3897 (4)	0.8482 (2)	0.0631 (10)
H6	1.0659	0.4603	0.8732	0.076*
C9	0.6350 (4)	0.0922 (3)	0.4507 (2)	0.0535 (8)
H9	0.7101	0.0268	0.4724	0.064*
C13	0.4817 (4)	0.2937 (4)	0.4769 (2)	0.0554 (8)
H13	0.4546	0.3616	0.5162	0.066*
O3	0.4181 (5)	0.0922 (4)	0.18766 (19)	0.0955 (11)
C12	0.4100 (5)	0.2880 (4)	0.3889 (3)	0.0580 (9)
H12	0.3340	0.3527	0.3674	0.070*
O4	0.2819 (6)	0.2721 (4)	0.2116 (3)	0.1064 (14)

	U11	U22	U33	U12	U13	U23
Br	0.0611 (3)	0.0868 (3)	0.0476 (3)	−0.00760 (19)	0.00100 (18)	−0.00065 (17)
O2	0.0682 (16)	0.0504 (12)	0.0479 (13)	−0.0114 (12)	−0.0034 (11)	0.0040 (11)
C1	0.0421 (17)	0.062 (2)	0.0475 (18)	0.0014 (14)	0.0051 (14)	−0.0012 (14)
O1	0.0684 (17)	0.0519 (14)	0.0599 (14)	−0.0047 (11)	0.0054 (12)	0.0080 (11)
C4	0.0445 (17)	0.0475 (16)	0.0456 (17)	0.0002 (14)	0.0079 (14)	−0.0012 (14)
C8	0.0480 (19)	0.0511 (17)	0.0434 (16)	−0.0075 (14)	0.0029 (14)	0.0044 (14)
C11	0.059 (2)	0.0515 (18)	0.0408 (16)	−0.0151 (16)	0.0091 (15)	0.0008 (14)
C10	0.067 (2)	0.0478 (18)	0.0534 (19)	−0.0115 (16)	0.0189 (17)	−0.0075 (14)
N1	0.094 (3)	0.067 (2)	0.0456 (17)	−0.030 (2)	0.0054 (17)	0.0047 (16)
C7	0.0460 (18)	0.0476 (18)	0.0531 (19)	−0.0014 (14)	0.0112 (15)	−0.0003 (15)
C5	0.060 (2)	0.058 (2)	0.059 (2)	−0.0160 (17)	0.0039 (16)	0.0070 (16)
C2	0.058 (2)	0.0476 (18)	0.0524 (18)	0.0002 (15)	0.0073 (16)	−0.0007 (14)
C3	0.054 (2)	0.0441 (17)	0.0509 (18)	−0.0044 (14)	0.0059 (15)	−0.0034 (14)
C6	0.061 (2)	0.067 (2)	0.059 (2)	−0.0197 (18)	0.0020 (18)	−0.0030 (17)
C9	0.057 (2)	0.0445 (17)	0.059 (2)	−0.0004 (15)	0.0105 (16)	0.0020 (14)
C13	0.056 (2)	0.0594 (19)	0.050 (2)	0.0043 (17)	0.0057 (16)	−0.0083 (16)
O3	0.148 (3)	0.092 (2)	0.0467 (15)	−0.027 (2)	0.0140 (18)	−0.0131 (15)
C12	0.057 (2)	0.062 (2)	0.053 (2)	0.0049 (17)	0.0034 (17)	0.0015 (16)
O4	0.137 (4)	0.105 (3)	0.063 (2)	0.011 (2)	−0.028 (2)	0.0082 (17)

Br—C1	1.896 (4)	C10—C9	1.379 (5)
O2—C7	1.379 (4)	C10—H10	0.9300
O2—C8	1.394 (4)	N1—O4	1.214 (5)
C1—C6	1.380 (5)	N1—O3	1.230 (5)
C1—C2	1.387 (5)	C5—C6	1.379 (5)
O1—C7	1.192 (4)	C5—H5	0.9300
C4—C3	1.383 (5)	C2—C3	1.378 (5)
C4—C5	1.388 (5)	C2—H2	0.9300
C4—C7	1.477 (5)	C3—H3	0.9300
C8—C9	1.378 (5)	C6—H6	0.9300
C8—C13	1.383 (5)	C9—H9	0.9300
C11—C10	1.372 (5)	C13—C12	1.367 (5)
C11—C12	1.387 (5)	C13—H13	0.9300
C11—N1	1.465 (4)	C12—H12	0.9300
C7—O2—C8	117.8 (3)	C6—C5—C4	120.5 (3)
C6—C1—C2	121.5 (3)	C6—C5—H5	119.8
C6—C1—Br	118.9 (3)	C4—C5—H5	119.8
C2—C1—Br	119.6 (3)	C3—C2—C1	118.5 (3)
C3—C4—C5	119.4 (3)	C3—C2—H2	120.7
C3—C4—C7	123.3 (3)	C1—C2—H2	120.7
C5—C4—C7	117.3 (3)	C2—C3—C4	121.0 (3)
C9—C8—C13	122.0 (3)	C2—C3—H3	119.5
C9—C8—O2	116.4 (3)	C4—C3—H3	119.5
C13—C8—O2	121.5 (3)	C5—C6—C1	119.0 (3)
C10—C11—C12	121.8 (3)	C5—C6—H6	120.5
C10—C11—N1	119.8 (3)	C1—C6—H6	120.5
C12—C11—N1	118.4 (4)	C8—C9—C10	118.9 (3)
C11—C10—C9	119.1 (3)	C8—C9—H9	120.5
C11—C10—H10	120.4	C10—C9—H9	120.5
C9—C10—H10	120.4	C12—C13—C8	118.9 (3)
O4—N1—O3	123.6 (4)	C12—C13—H13	120.5
O4—N1—C11	118.9 (4)	C8—C13—H13	120.5
O3—N1—C11	117.5 (4)	C13—C12—C11	119.2 (4)
O1—C7—O2	122.4 (3)	C13—C12—H12	120.4
O1—C7—C4	126.2 (3)	C11—C12—H12	120.4
O2—C7—C4	111.4 (3)
C7—O2—C8—C9	123.0 (3)	C6—C1—C2—C3	1.3 (5)
C7—O2—C8—C13	−60.4 (4)	Br—C1—C2—C3	179.9 (3)
C12—C11—C10—C9	−1.7 (5)	C1—C2—C3—C4	−0.3 (5)
N1—C11—C10—C9	177.2 (3)	C5—C4—C3—C2	−1.2 (5)
C10—C11—N1—O4	−179.4 (4)	C7—C4—C3—C2	−179.6 (3)
C12—C11—N1—O4	−0.4 (6)	C4—C5—C6—C1	−0.7 (6)
C10—C11—N1—O3	0.0 (5)	C2—C1—C6—C5	−0.9 (6)
C12—C11—N1—O3	178.9 (4)	Br—C1—C6—C5	−179.5 (3)
C8—O2—C7—O1	0.6 (5)	C13—C8—C9—C10	1.5 (5)
C8—O2—C7—C4	−178.4 (3)	O2—C8—C9—C10	178.1 (3)
C3—C4—C7—O1	173.0 (4)	C11—C10—C9—C8	0.4 (5)
C5—C4—C7—O1	−5.4 (5)	C9—C8—C13—C12	−2.0 (6)
C3—C4—C7—O2	−8.0 (5)	O2—C8—C13—C12	−178.5 (3)
C5—C4—C7—O2	173.5 (3)	C8—C13—C12—C11	0.7 (6)
C3—C4—C5—C6	1.7 (6)	C10—C11—C12—C13	1.2 (6)
C7—C4—C5—C6	−179.8 (4)	N1—C11—C12—C13	−177.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O4i	0.93	2.69	3.543 (6)	153.
C3—H3···O3ii	0.93	2.60	3.335 (5)	136.
C13—H13···O3iii	0.93	2.67	3.460 (5)	143.
C12—H12···O1iv	0.93	2.50	3.237 (5)	137.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O4i	0.93	2.69	3.543 (6)	153
C3—H3⋯O3ii	0.93	2.60	3.335 (5)	136
C13—H13⋯O3iii	0.93	2.67	3.460 (5)	143
C12—H12⋯O1iv	0.93	2.50	3.237 (5)	137

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .