2,4,6-Tri-nitro-phenyl 4-bromo-benzoate.

In the title benzoate derivative, C13H6BrN3O8, the benzene rings form a dihedral angle of 80.90 (9)°. The ester moiety forms dihedral angles of 3.2 (2) and 82.8 4(10)° with the benzene and picryl rings, respectively. The Br atom is disordered over two positions, with the site occupancy for the minor component being 0.48 (4). The crystal structure features C-H⋯O inter-actions, which generate a three-dimensional network.

Related literature

For similar esters, see: Moreno-Fuquen et al. (2013 ▶). For hydrogen bonding, see: Nardelli (1995 ▶).

Experimental

Crystal data

C13H6BrN3O8

M = 412.12

Monoclinic,

a = 10.8409 (5) Å

b = 10.0152 (7) Å

c = 13.9777 (7) Å

β = 99.246 (3)°

V = 1497.89 (15) Å3

Z = 4

Mo Kα radiation

μ = 2.80 mm−1

T = 295 K

0.34 × 0.13 × 0.11 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.668, T max = 0.753

10473 measured reflections

3340 independent reflections

2092 reflections with I > 2σ(I)

R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.134

S = 1.02

3340 reflections

236 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.50 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: SIR92 (Altomare et al., 1994 ▶); 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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813031061/tk5272sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813031061/tk5272Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813031061/tk5272Isup3.cml

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

C13H6BrN3O8	F(000) = 816
Mr = 412.12	Dx = 1.827 Mg m−3
Monoclinic, P21/c	Melting point: 457(1) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.8409 (5) Å	Cell parameters from 6103 reflections
b = 10.0152 (7) Å	θ = 2.9–27.5°
c = 13.9777 (7) Å	µ = 2.80 mm−1
β = 99.246 (3)°	T = 295 K
V = 1497.89 (15) Å3	Block, pale yellow
Z = 4	0.34 × 0.13 × 0.11 mm

Nonius KappaCCD diffractometer	3340 independent reflections
Radiation source: fine-focus sealed tube	2092 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.060
CCD rotation images, thick slices scans	θmax = 27.6°, θmin = 3.3°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −14→13
Tmin = 0.668, Tmax = 0.753	k = −11→13
10473 measured reflections	l = −18→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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0632P)2 + 0.3604P] where P = (Fo2 + 2Fc2)/3
3340 reflections	(Δ/σ)max < 0.001
236 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.50 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	Occ. (<1)
Br1A	0.3092 (13)	0.2505 (17)	0.2655 (8)	0.100 (2)	0.48 (4)
Br1B	0.2896 (6)	0.2267 (6)	0.2775 (5)	0.0781 (10)	0.52 (4)
O7	0.70356 (18)	0.2879 (2)	0.69502 (15)	0.0547 (5)
O8	0.8026 (2)	0.1287 (3)	0.62476 (17)	0.0831 (8)
N1	0.6967 (3)	0.0905 (3)	0.8454 (2)	0.0606 (7)
C13	0.6090 (3)	0.1222 (3)	0.4631 (2)	0.0517 (7)
H13	0.6728	0.0598	0.4646	0.062*
N3	0.9026 (2)	0.4791 (3)	0.7109 (2)	0.0630 (7)
O6	0.8478 (3)	0.4642 (3)	0.62908 (16)	0.0870 (8)
C6	0.8938 (3)	0.3763 (3)	0.78448 (19)	0.0475 (6)
O1	0.6128 (3)	0.0871 (3)	0.7775 (2)	0.0940 (9)
C8	0.6080 (3)	0.2073 (3)	0.5414 (2)	0.0478 (7)
C5	0.9857 (3)	0.3788 (3)	0.8661 (2)	0.0515 (7)
H5	1.0486	0.4429	0.8731	0.062*
O2	0.7002 (3)	0.0195 (3)	0.9141 (2)	0.1052 (11)
O4	1.1481 (3)	0.3782 (3)	1.0350 (2)	0.0979 (10)
O5	0.9625 (3)	0.5792 (3)	0.7381 (2)	0.1012 (10)
C12	0.5168 (3)	0.1292 (3)	0.3836 (2)	0.0579 (8)
H12	0.5183	0.0729	0.3308	0.070*
C7	0.7141 (3)	0.1995 (3)	0.6211 (2)	0.0525 (7)
C3	0.8886 (3)	0.1888 (3)	0.9281 (2)	0.0496 (7)
H3	0.8878	0.1250	0.9764	0.060*
C4	0.9808 (3)	0.2838 (3)	0.9359 (2)	0.0501 (7)
N2	1.0775 (3)	0.2846 (3)	1.0231 (2)	0.0663 (8)
C1	0.7978 (2)	0.2826 (3)	0.77309 (18)	0.0456 (6)
O3	1.0787 (3)	0.1913 (3)	1.0790 (2)	0.1036 (10)
C2	0.7973 (3)	0.1898 (3)	0.84741 (19)	0.0472 (6)
C9	0.5104 (3)	0.2978 (4)	0.5407 (2)	0.0615 (8)
H9	0.5080	0.3537	0.5935	0.074*
C10	0.4172 (3)	0.3040 (4)	0.4609 (3)	0.0714 (10)
H10	0.3515	0.3640	0.4597	0.086*
C11	0.4220 (3)	0.2211 (3)	0.3833 (2)	0.0621 (8)

	U11	U22	U33	U12	U13	U23
Br1A	0.086 (3)	0.139 (4)	0.0585 (17)	0.037 (2)	−0.0375 (19)	−0.026 (2)
Br1B	0.0657 (12)	0.087 (2)	0.0686 (17)	0.0096 (11)	−0.0283 (9)	−0.0107 (9)
O7	0.0510 (11)	0.0685 (13)	0.0392 (10)	0.0097 (9)	−0.0088 (8)	−0.0089 (10)
O8	0.0712 (15)	0.104 (2)	0.0630 (14)	0.0406 (14)	−0.0233 (11)	−0.0294 (14)
N1	0.0652 (16)	0.0599 (16)	0.0532 (15)	−0.0119 (13)	−0.0010 (13)	−0.0088 (13)
C13	0.0490 (15)	0.0539 (17)	0.0486 (15)	0.0026 (12)	−0.0027 (13)	−0.0045 (14)
N3	0.0569 (15)	0.0748 (19)	0.0550 (16)	0.0002 (14)	0.0021 (12)	0.0124 (14)
O6	0.124 (2)	0.0891 (19)	0.0434 (13)	0.0033 (16)	0.0012 (14)	0.0082 (13)
C6	0.0503 (15)	0.0517 (16)	0.0384 (14)	0.0037 (12)	0.0008 (11)	0.0024 (13)
O1	0.0849 (17)	0.095 (2)	0.0896 (19)	−0.0353 (15)	−0.0253 (15)	0.0026 (16)
C8	0.0465 (14)	0.0545 (17)	0.0392 (14)	0.0024 (12)	−0.0029 (12)	−0.0010 (13)
C5	0.0476 (15)	0.0572 (17)	0.0470 (16)	−0.0027 (12)	−0.0004 (12)	−0.0035 (14)
O2	0.120 (2)	0.112 (2)	0.0748 (18)	−0.060 (2)	−0.0083 (17)	0.0232 (17)
O4	0.0877 (18)	0.113 (2)	0.0782 (18)	−0.0375 (17)	−0.0326 (14)	0.0049 (16)
O5	0.0850 (18)	0.102 (2)	0.103 (2)	−0.0365 (16)	−0.0261 (16)	0.0474 (18)
C12	0.0588 (17)	0.0632 (19)	0.0469 (16)	0.0008 (14)	−0.0062 (13)	−0.0123 (15)
C7	0.0522 (16)	0.0636 (19)	0.0378 (15)	0.0066 (14)	−0.0042 (12)	−0.0073 (14)
C3	0.0576 (16)	0.0526 (17)	0.0361 (14)	0.0007 (13)	−0.0002 (12)	−0.0006 (13)
C4	0.0478 (15)	0.0589 (18)	0.0392 (15)	0.0009 (13)	−0.0061 (12)	−0.0030 (14)
N2	0.0621 (16)	0.080 (2)	0.0495 (15)	−0.0071 (15)	−0.0141 (13)	0.0007 (15)
C1	0.0439 (14)	0.0572 (17)	0.0326 (13)	0.0046 (12)	−0.0036 (11)	−0.0070 (12)
O3	0.105 (2)	0.112 (2)	0.0749 (18)	−0.0181 (18)	−0.0409 (17)	0.0316 (18)
C2	0.0508 (15)	0.0494 (16)	0.0394 (14)	−0.0040 (12)	0.0011 (12)	−0.0071 (13)
C9	0.0556 (17)	0.075 (2)	0.0479 (17)	0.0163 (16)	−0.0087 (14)	−0.0156 (16)
C10	0.0628 (19)	0.086 (3)	0.058 (2)	0.0252 (18)	−0.0121 (16)	−0.0195 (19)
C11	0.0549 (17)	0.075 (2)	0.0489 (17)	0.0057 (15)	−0.0149 (14)	−0.0107 (16)

Br1A—C11	1.909 (7)	C8—C7	1.469 (4)
Br1B—C11	1.889 (6)	C5—C4	1.371 (4)
O7—C1	1.371 (3)	C5—H5	0.9300
O7—C7	1.379 (4)	O4—N2	1.205 (4)
O8—C7	1.188 (4)	C12—C11	1.380 (5)
N1—O2	1.191 (4)	C12—H12	0.9300
N1—O1	1.205 (3)	C3—C4	1.372 (4)
N1—C2	1.473 (4)	C3—C2	1.376 (4)
C13—C12	1.371 (4)	C3—H3	0.9300
C13—C8	1.389 (4)	C4—N2	1.474 (4)
C13—H13	0.9300	N2—O3	1.217 (4)
N3—O6	1.210 (3)	C1—C2	1.394 (4)
N3—O5	1.222 (4)	C9—C10	1.381 (4)
N3—C6	1.469 (4)	C9—H9	0.9300
C6—C5	1.389 (4)	C10—C11	1.374 (5)
C6—C1	1.392 (4)	C10—H10	0.9300
C8—C9	1.392 (4)
C1—O7—C7	115.5 (2)	C4—C3—H3	120.7
O2—N1—O1	122.8 (3)	C2—C3—H3	120.7
O2—N1—C2	117.4 (3)	C5—C4—C3	122.4 (3)
O1—N1—C2	119.8 (3)	C5—C4—N2	118.8 (3)
C12—C13—C8	120.7 (3)	C3—C4—N2	118.8 (3)
C12—C13—H13	119.6	O4—N2—O3	124.6 (3)
C8—C13—H13	119.6	O4—N2—C4	118.0 (3)
O6—N3—O5	123.5 (3)	O3—N2—C4	117.4 (3)
O6—N3—C6	119.9 (3)	O7—C1—C6	120.8 (2)
O5—N3—C6	116.6 (3)	O7—C1—C2	121.9 (2)
C5—C6—C1	122.1 (3)	C6—C1—C2	117.2 (2)
C5—C6—N3	116.4 (3)	C3—C2—C1	121.9 (3)
C1—C6—N3	121.6 (2)	C3—C2—N1	116.3 (3)
C13—C8—C9	119.7 (3)	C1—C2—N1	121.8 (2)
C13—C8—C7	117.5 (2)	C10—C9—C8	119.5 (3)
C9—C8—C7	122.8 (3)	C10—C9—H9	120.3
C4—C5—C6	117.9 (3)	C8—C9—H9	120.3
C4—C5—H5	121.0	C11—C10—C9	119.6 (3)
C6—C5—H5	121.0	C11—C10—H10	120.2
C13—C12—C11	118.8 (3)	C9—C10—H10	120.2
C13—C12—H12	120.6	C10—C11—C12	121.6 (3)
C11—C12—H12	120.6	C10—C11—Br1B	118.7 (3)
O8—C7—O7	121.0 (3)	C12—C11—Br1B	119.6 (3)
O8—C7—C8	126.3 (3)	C10—C11—Br1A	119.2 (3)
O7—C7—C8	112.7 (2)	C12—C11—Br1A	118.6 (3)
C4—C3—C2	118.6 (3)
O6—N3—C6—C5	161.2 (3)	C7—O7—C1—C2	−83.5 (3)
O5—N3—C6—C5	−21.7 (4)	C5—C6—C1—O7	175.6 (3)
O6—N3—C6—C1	−19.3 (4)	N3—C6—C1—O7	−3.9 (4)
O5—N3—C6—C1	157.8 (3)	C5—C6—C1—C2	−0.1 (4)
C12—C13—C8—C9	2.1 (5)	N3—C6—C1—C2	−179.6 (3)
C12—C13—C8—C7	−176.2 (3)	C4—C3—C2—C1	1.3 (4)
C1—C6—C5—C4	1.0 (4)	C4—C3—C2—N1	−176.6 (3)
N3—C6—C5—C4	−179.6 (3)	O7—C1—C2—C3	−176.7 (2)
C8—C13—C12—C11	−0.9 (5)	C6—C1—C2—C3	−1.0 (4)
C1—O7—C7—O8	−3.2 (5)	O7—C1—C2—N1	1.2 (4)
C1—O7—C7—C8	178.0 (2)	C6—C1—C2—N1	176.8 (3)
C13—C8—C7—O8	1.5 (5)	O2—N1—C2—C3	1.7 (4)
C9—C8—C7—O8	−176.8 (4)	O1—N1—C2—C3	179.0 (3)
C13—C8—C7—O7	−179.9 (3)	O2—N1—C2—C1	−176.2 (3)
C9—C8—C7—O7	1.8 (4)	O1—N1—C2—C1	1.1 (4)
C6—C5—C4—C3	−0.7 (4)	C13—C8—C9—C10	−1.6 (5)
C6—C5—C4—N2	180.0 (3)	C7—C8—C9—C10	176.7 (3)
C2—C3—C4—C5	−0.5 (5)	C8—C9—C10—C11	−0.1 (6)
C2—C3—C4—N2	178.9 (3)	C9—C10—C11—C12	1.3 (6)
C5—C4—N2—O4	8.8 (5)	C9—C10—C11—Br1B	177.4 (4)
C3—C4—N2—O4	−170.6 (3)	C9—C10—C11—Br1A	−169.6 (9)
C5—C4—N2—O3	−172.5 (3)	C13—C12—C11—C10	−0.8 (6)
C3—C4—N2—O3	8.1 (5)	C13—C12—C11—Br1B	−176.9 (3)
C7—O7—C1—C6	101.0 (3)	C13—C12—C11—Br1A	170.2 (8)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O2i	0.93	2.48	3.169 (4)	131
C12—H12···O1ii	0.93	2.49	3.273 (4)	142
C5—H5···O8iii	0.93	2.46	3.384 (4)	173
C3—H3···O6iv	0.93	2.42	3.291 (4)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O2i	0.93	2.48	3.169 (4)	131
C12—H12⋯O1ii	0.93	2.49	3.273 (4)	142
C5—H5⋯O8iii	0.93	2.46	3.384 (4)	173
C3—H3⋯O6iv	0.93	2.42	3.291 (4)	157

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