2,4,6-Trinitro-phenyl benzoate.

In the title mol-ecule, C13H7N3O8, the phenyl and benzene rings are rotated from the mean plane of the central ester group by 18.41 (9) and 81.80 (5)°, respectively. The dihedral angle between the rings is 80.12 (14)°. In the crystal, mol-ecules are linked by weak C-H⋯O inter-actions, forming helical chains along [010].

Related literature

For theoretical and spectroscopic properties of nitro­phenyl esters, see: Ibrahim et al. (2011 ▶); Kirkien-Konasievicz & Maccoll (1964 ▶). For the structures of similar esters, see: Moreno-Fuquen et al. (2012a ▶,b ▶); Shibakami & Sekiya (1995 ▶); Gowda et al. (2007 ▶). For structural properties of nitro­phenyl compounds, see: Domenicano et al. (1990 ▶); Glidewell et al. (2005 ▶). For hydrogen-bonding information, see: Nardelli (1995 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C13H7N3O8

M = 333.22

Orthorhombic,

a = 7.5818 (3) Å

b = 8.3714 (2) Å

c = 21.0625 (10) Å

V = 1336.84 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.14 mm−1

T = 123 K

0.31 × 0.21 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur E diffractometer

5179 measured reflections

2758 independent reflections

2563 reflections with I > 2σ(I)’

R int = 0.019

Standard reflections: 0

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.073

S = 1.05

2758 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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/S1600536812048362/lh5562sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812048362/lh5562Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812048362/lh5562Isup3.cml

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

C13H7N3O8	Dx = 1.656 Mg m−3
Mr = 333.22	Melting point: 435(1) K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5179 reflections
a = 7.5818 (3) Å	θ = 2.9–27.0°
b = 8.3714 (2) Å	µ = 0.14 mm−1
c = 21.0625 (10) Å	T = 123 K
V = 1336.84 (9) Å3	Block, pale-yellow
Z = 4	0.31 × 0.21 × 0.12 mm
F(000) = 680

Oxford Diffraction Xcalibur E diffractometer	2563 reflections with I > 2σ(I)'
Radiation source: fine-focus sealed tube	Rint = 0.019
Graphite monochromator	θmax = 27.0°, θmin = 2.9°
ω scans	h = −9→8
5179 measured reflections	k = −10→10
2758 independent reflections	l = −26→23

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.073	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0354P)2 + 0.1599P] where P = (Fo2 + 2Fc2)/3
2758 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.21 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
O1	0.11331 (19)	0.69680 (17)	0.15456 (6)	0.0370 (3)
O2	−0.03793 (16)	0.51649 (14)	0.20396 (6)	0.0265 (3)
O3	−0.10783 (19)	0.58818 (19)	0.43018 (7)	0.0423 (4)
O4	0.07057 (19)	0.74602 (16)	0.48041 (6)	0.0344 (3)
O5	0.6229 (2)	0.8632 (2)	0.38383 (7)	0.0479 (4)
O6	0.65305 (16)	0.87515 (14)	0.28252 (6)	0.0275 (3)
O7	0.42129 (15)	0.73147 (12)	0.21060 (5)	0.0182 (2)
O8	0.35960 (15)	0.99125 (13)	0.19172 (5)	0.0205 (3)
N1	0.07053 (19)	0.62411 (16)	0.20235 (6)	0.0207 (3)
N2	0.01984 (19)	0.67714 (17)	0.43257 (7)	0.0246 (3)
N3	0.56820 (19)	0.84505 (16)	0.33002 (7)	0.0219 (3)
C1	0.3206 (2)	0.73479 (17)	0.26457 (8)	0.0159 (3)
C2	0.1511 (2)	0.67083 (17)	0.26317 (8)	0.0170 (3)
C3	0.0513 (2)	0.64857 (17)	0.31728 (8)	0.0186 (3)
H3	−0.0619	0.6002	0.3155	0.022*
C4	0.1230 (2)	0.69963 (18)	0.37407 (8)	0.0192 (3)
C5	0.2881 (2)	0.76870 (18)	0.37826 (8)	0.0194 (3)
H5	0.3328	0.8051	0.4178	0.023*
C6	0.3864 (2)	0.78346 (17)	0.32340 (8)	0.0177 (3)
C7	0.4341 (2)	0.87175 (17)	0.17581 (7)	0.0168 (3)
C8	0.5485 (2)	0.84810 (18)	0.12011 (7)	0.0170 (3)
C9	0.6668 (2)	0.7207 (2)	0.11679 (8)	0.0237 (4)
H9	0.6743	0.6461	0.1506	0.028*
C10	0.7730 (2)	0.7040 (2)	0.06380 (9)	0.0309 (4)
H10	0.8530	0.6170	0.0610	0.037*
C11	0.7630 (2)	0.8137 (2)	0.01489 (9)	0.0268 (4)
H11	0.8373	0.8020	−0.0211	0.032*
C12	0.6461 (2)	0.94018 (19)	0.01778 (8)	0.0206 (3)
H12	0.6403	1.0150	−0.0161	0.025*
C13	0.5369 (2)	0.95746 (18)	0.07042 (7)	0.0178 (3)
H13	0.4550	1.0432	0.0725	0.021*

	U11	U22	U33	U12	U13	U23
O1	0.0388 (8)	0.0502 (8)	0.0220 (7)	−0.0188 (7)	−0.0061 (6)	0.0083 (6)
O2	0.0218 (6)	0.0228 (5)	0.0347 (7)	−0.0062 (5)	−0.0041 (6)	−0.0043 (5)
O3	0.0269 (7)	0.0656 (9)	0.0345 (8)	−0.0114 (8)	0.0099 (6)	0.0052 (7)
O4	0.0417 (8)	0.0419 (7)	0.0197 (6)	0.0053 (7)	0.0050 (6)	−0.0049 (6)
O5	0.0378 (8)	0.0807 (11)	0.0254 (8)	−0.0282 (9)	−0.0114 (7)	0.0050 (7)
O6	0.0211 (6)	0.0316 (6)	0.0299 (7)	−0.0083 (6)	0.0011 (6)	0.0042 (6)
O7	0.0190 (6)	0.0165 (5)	0.0190 (6)	−0.0007 (5)	0.0043 (5)	0.0018 (4)
O8	0.0201 (6)	0.0188 (5)	0.0227 (6)	0.0028 (5)	0.0031 (5)	0.0011 (5)
N1	0.0169 (7)	0.0223 (6)	0.0230 (7)	−0.0011 (6)	0.0003 (6)	−0.0027 (6)
N2	0.0214 (7)	0.0292 (7)	0.0233 (8)	0.0068 (7)	0.0044 (7)	0.0035 (6)
N3	0.0204 (7)	0.0217 (6)	0.0236 (8)	−0.0044 (6)	−0.0037 (6)	0.0032 (6)
C1	0.0179 (8)	0.0120 (6)	0.0178 (8)	0.0017 (6)	0.0023 (6)	0.0019 (6)
C2	0.0171 (8)	0.0143 (6)	0.0195 (8)	0.0010 (7)	−0.0012 (7)	−0.0010 (6)
C3	0.0154 (7)	0.0162 (7)	0.0241 (8)	0.0011 (7)	0.0022 (7)	0.0015 (6)
C4	0.0189 (8)	0.0177 (7)	0.0211 (9)	0.0037 (7)	0.0040 (7)	0.0026 (6)
C5	0.0231 (8)	0.0160 (7)	0.0190 (8)	0.0027 (7)	−0.0027 (7)	−0.0001 (6)
C6	0.0151 (8)	0.0147 (6)	0.0232 (8)	−0.0011 (6)	−0.0026 (7)	0.0020 (6)
C7	0.0138 (7)	0.0176 (7)	0.0188 (8)	−0.0026 (7)	−0.0030 (6)	0.0016 (6)
C8	0.0145 (7)	0.0188 (7)	0.0176 (8)	−0.0036 (7)	−0.0002 (7)	0.0005 (6)
C9	0.0211 (8)	0.0263 (8)	0.0237 (9)	0.0051 (8)	0.0011 (7)	0.0033 (7)
C10	0.0266 (9)	0.0330 (9)	0.0329 (10)	0.0116 (9)	0.0076 (9)	0.0032 (8)
C11	0.0220 (9)	0.0338 (9)	0.0244 (9)	0.0038 (8)	0.0078 (8)	−0.0007 (7)
C12	0.0205 (9)	0.0236 (7)	0.0176 (8)	−0.0039 (7)	0.0006 (7)	0.0008 (6)
C13	0.0153 (8)	0.0177 (7)	0.0203 (8)	−0.0007 (7)	−0.0014 (7)	−0.0011 (6)

O1—N1	1.2201 (18)	C3—H3	0.9500
O2—N1	1.2203 (17)	C4—C5	1.382 (2)
O3—N2	1.222 (2)	C5—C6	1.381 (2)
O4—N2	1.2231 (18)	C5—H5	0.9500
O5—N3	1.2166 (19)	C7—C8	1.473 (2)
O6—N3	1.2158 (17)	C8—C13	1.393 (2)
O7—C1	1.3695 (19)	C8—C9	1.395 (2)
O7—C7	1.3876 (17)	C9—C10	1.383 (2)
O8—C7	1.1965 (18)	C9—H9	0.9500
N1—C2	1.472 (2)	C10—C11	1.382 (3)
N2—C4	1.471 (2)	C10—H10	0.9500
N3—C6	1.478 (2)	C11—C12	1.382 (2)
C1—C2	1.393 (2)	C11—H11	0.9500
C1—C6	1.396 (2)	C12—C13	1.391 (2)
C2—C3	1.381 (2)	C12—H12	0.9500
C3—C4	1.382 (2)	C13—H13	0.9500
C1—O7—C7	117.39 (11)	C5—C6—C1	121.58 (14)
O1—N1—O2	124.77 (14)	C5—C6—N3	117.12 (14)
O1—N1—C2	118.37 (13)	C1—C6—N3	121.22 (15)
O2—N1—C2	116.84 (13)	O8—C7—O7	121.79 (14)
O3—N2—O4	124.76 (16)	O8—C7—C8	127.85 (14)
O3—N2—C4	117.67 (15)	O7—C7—C8	110.37 (12)
O4—N2—C4	117.55 (14)	C13—C8—C9	120.35 (15)
O6—N3—O5	124.07 (15)	C13—C8—C7	118.21 (14)
O6—N3—C6	119.22 (14)	C9—C8—C7	121.43 (14)
O5—N3—C6	116.70 (14)	C10—C9—C8	119.47 (16)
O7—C1—C2	119.27 (14)	C10—C9—H9	120.3
O7—C1—C6	122.92 (14)	C8—C9—H9	120.3
C2—C1—C6	117.42 (14)	C11—C10—C9	120.15 (16)
C3—C2—C1	122.70 (15)	C11—C10—H10	119.9
C3—C2—N1	117.07 (14)	C9—C10—H10	119.9
C1—C2—N1	120.24 (14)	C10—C11—C12	120.75 (16)
C2—C3—C4	117.22 (15)	C10—C11—H11	119.6
C2—C3—H3	121.4	C12—C11—H11	119.6
C4—C3—H3	121.4	C11—C12—C13	119.75 (16)
C3—C4—C5	122.76 (16)	C11—C12—H12	120.1
C3—C4—N2	118.45 (14)	C13—C12—H12	120.1
C5—C4—N2	118.79 (15)	C12—C13—C8	119.52 (15)
C6—C5—C4	118.24 (15)	C12—C13—H13	120.2
C6—C5—H5	120.9	C8—C13—H13	120.2
C4—C5—H5	120.9
C7—O7—C1—C2	101.44 (16)	O7—C1—C6—C5	−172.62 (13)
C7—O7—C1—C6	−85.90 (18)	C2—C1—C6—C5	0.2 (2)
O7—C1—C2—C3	170.39 (13)	O7—C1—C6—N3	4.1 (2)
C6—C1—C2—C3	−2.7 (2)	C2—C1—C6—N3	176.85 (13)
O7—C1—C2—N1	−9.8 (2)	O6—N3—C6—C5	−172.63 (14)
C6—C1—C2—N1	177.14 (13)	O5—N3—C6—C5	7.0 (2)
O1—N1—C2—C3	149.89 (15)	O6—N3—C6—C1	10.5 (2)
O2—N1—C2—C3	−28.6 (2)	O5—N3—C6—C1	−169.84 (16)
O1—N1—C2—C1	−29.9 (2)	C1—O7—C7—O8	−0.5 (2)
O2—N1—C2—C1	151.56 (14)	C1—O7—C7—C8	179.19 (13)
C1—C2—C3—C4	3.0 (2)	O8—C7—C8—C13	−18.8 (3)
N1—C2—C3—C4	−176.85 (13)	O7—C7—C8—C13	161.59 (14)
C2—C3—C4—C5	−0.8 (2)	O8—C7—C8—C9	160.83 (17)
C2—C3—C4—N2	−179.85 (13)	O7—C7—C8—C9	−18.8 (2)
O3—N2—C4—C3	13.6 (2)	C13—C8—C9—C10	0.2 (3)
O4—N2—C4—C3	−168.01 (14)	C7—C8—C9—C10	−179.38 (16)
O3—N2—C4—C5	−165.48 (15)	C8—C9—C10—C11	0.6 (3)
O4—N2—C4—C5	12.9 (2)	C9—C10—C11—C12	−0.7 (3)
C3—C4—C5—C6	−1.6 (2)	C10—C11—C12—C13	−0.1 (3)
N2—C4—C5—C6	177.51 (14)	C11—C12—C13—C8	0.9 (2)
C4—C5—C6—C1	1.9 (2)	C9—C8—C13—C12	−1.0 (2)
C4—C5—C6—N3	−174.95 (13)	C7—C8—C13—C12	178.63 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O8i	0.95	2.44	3.388 (2)	177

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O8i	0.95	2.44	3.388 (2)	177

Symmetry code: (i) .