2,4,6-Trinitro-phenyl 4-chloro-benzoate.

In the title benzoate derivative, C13H6ClN3O8, the planes of the benzene rings form a dihedral angle of 63.46 (5)°. The dihedral angles between the benzene ring and its nitro groups are 12.78 (16)° for the first ortho, 28.4 (4) and 17.4 (4)° for the second (disordered) ortho and 3.58 (16)° for the para nitro group. The central ester moiety, -C-(C=O)-O-, is essentially planar (r.m.s. deviation for all non-H atoms = 0.0229 Å) and forms dihedral angles of 7.37 (14)° with the chloro-substituted benzene ring and 69.85 (6)° with the trinitro-substituted benzene ring. One of the nitro groups was refined as disordered over two sets of sites with fixed site occupancies of 0.61 and 0.39. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For the industrial and synthetic applications of nitroaryl compounds, see: Moreno-Fuquen et al. (2012a ▶) and references therein. For similar structures, see: Moreno-Fuquen et al. (2012b ▶,c ▶). For hydrogen bonding, see: Nardelli (1995 ▶). For hydrogen-bond motifs, see: Etter et al. (1990 ▶). For a description of the Cambridge Structural Database (CSD), see: Allen (2002 ▶).

Experimental

Crystal data

C13H6ClN3O8

M = 367.66

Monoclinic,

a = 9.3526 (3) Å

b = 11.4793 (3) Å

c = 13.6089 (4) Å

β = 93.612 (2)°

V = 1458.17 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.32 mm−1

T = 295 K

0.35 × 0.31 × 0.24 mm

Data collection

Nonius KappaCCD diffractometer

15908 measured reflections

3288 independent reflections

2424 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.151

S = 1.02

3288 reflections

246 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.24 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/S1600536813007332/lh5591sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813007332/lh5591Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813007332/lh5591Isup3.cml

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

C13H6ClN3O8	F(000) = 744
Mr = 367.66	Dx = 1.675 Mg m−3
Monoclinic, P21/c	Melting point: 433(1) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.3526 (3) Å	Cell parameters from 7848 reflections
b = 11.4793 (3) Å	θ = 2.6–27.5°
c = 13.6089 (4) Å	µ = 0.32 mm−1
β = 93.612 (2)°	T = 295 K
V = 1458.17 (7) Å3	Block, pale-yellow
Z = 4	0.35 × 0.31 × 0.24 mm

Nonius KappaCCD diffractometer	2424 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.040
Graphite monochromator	θmax = 27.5°, θmin = 2.8°
CCD rotation images, thick slices scans	h = −12→12
15908 measured reflections	k = −14→14
3288 independent reflections	l = −17→17

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048	H-atom parameters constrained
wR(F2) = 0.151	w = 1/[σ2(Fo2) + (0.091P)2 + 0.2737P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
3288 reflections	Δρmax = 0.30 e Å−3
246 parameters	Δρmin = −0.24 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.045 (6)

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)
Cl1	0.70639 (6)	0.72855 (7)	1.22374 (4)	0.0773 (3)
N1	0.2976 (2)	0.57696 (14)	0.65153 (12)	0.0561 (4)
N2	−0.07414 (19)	0.80404 (16)	0.47344 (13)	0.0582 (4)
N3	0.1244 (2)	0.95193 (16)	0.78955 (13)	0.0630 (5)
O1	0.40062 (19)	0.57284 (15)	0.70877 (13)	0.0772 (5)
O2	0.2690 (3)	0.50235 (18)	0.59209 (18)	0.1161 (9)
O3	−0.0786 (2)	0.72668 (17)	0.41290 (15)	0.0935 (7)
O4	−0.14293 (19)	0.89346 (16)	0.46545 (13)	0.0783 (5)
O5A	0.0210 (6)	1.0035 (5)	0.7997 (4)	0.1039 (15)	0.61
O6A	0.2343 (8)	0.9689 (6)	0.8395 (6)	0.169 (3)	0.61
O5B	0.0649 (8)	1.0471 (5)	0.7629 (5)	0.0839 (18)	0.39
O6B	0.1736 (9)	0.9336 (6)	0.8683 (3)	0.083 (2)	0.39
O7	0.31371 (15)	0.75992 (11)	0.80241 (10)	0.0511 (3)
O8	0.19504 (17)	0.61439 (15)	0.87062 (11)	0.0698 (5)
C1	0.21381 (19)	0.76369 (15)	0.72449 (12)	0.0427 (4)
C2	0.20321 (19)	0.67959 (15)	0.65074 (12)	0.0438 (4)
C3	0.1074 (2)	0.69124 (15)	0.56973 (13)	0.0469 (4)
H3	0.1000	0.6339	0.5214	0.056*
C4	0.0233 (2)	0.78926 (15)	0.56216 (13)	0.0461 (4)
C5	0.0276 (2)	0.87387 (16)	0.63325 (13)	0.0479 (4)
H5	−0.0319	0.9387	0.6274	0.057*
C6	0.1229 (2)	0.85976 (15)	0.71372 (12)	0.0455 (4)
C7	0.2931 (2)	0.67990 (16)	0.87591 (12)	0.0457 (4)
C8	0.40200 (19)	0.69270 (15)	0.95775 (12)	0.0435 (4)
C9	0.5009 (2)	0.78335 (17)	0.96322 (14)	0.0522 (5)
H9	0.5037	0.8366	0.9119	0.063*
C10	0.5950 (2)	0.79402 (19)	1.04504 (15)	0.0574 (5)
H10	0.6607	0.8549	1.0494	0.069*
C11	0.5907 (2)	0.71382 (18)	1.12019 (14)	0.0528 (5)
C12	0.4945 (2)	0.62241 (17)	1.11557 (13)	0.0513 (4)
H12	0.4936	0.5687	1.1667	0.062*
C13	0.3999 (2)	0.61173 (16)	1.03421 (12)	0.0469 (4)
H13	0.3346	0.5505	1.0302	0.056*

	U11	U22	U33	U12	U13	U23
Cl1	0.0639 (4)	0.1147 (6)	0.0505 (3)	−0.0004 (3)	−0.0189 (2)	0.0022 (3)
N1	0.0678 (11)	0.0510 (9)	0.0490 (9)	0.0095 (7)	0.0005 (8)	0.0062 (7)
N2	0.0568 (10)	0.0640 (10)	0.0517 (9)	−0.0021 (8)	−0.0134 (7)	0.0040 (8)
N3	0.0814 (13)	0.0564 (10)	0.0505 (10)	0.0037 (9)	−0.0019 (9)	−0.0080 (8)
O1	0.0779 (11)	0.0792 (11)	0.0725 (11)	0.0261 (9)	−0.0106 (9)	0.0079 (8)
O2	0.150 (2)	0.0794 (12)	0.1119 (16)	0.0508 (13)	−0.0479 (14)	−0.0421 (12)
O3	0.1134 (16)	0.0845 (12)	0.0754 (12)	0.0096 (10)	−0.0499 (11)	−0.0188 (9)
O4	0.0763 (11)	0.0838 (11)	0.0717 (10)	0.0233 (9)	−0.0195 (8)	0.0077 (8)
O5A	0.119 (4)	0.093 (3)	0.100 (4)	0.039 (3)	0.012 (2)	−0.036 (3)
O6A	0.159 (6)	0.114 (4)	0.217 (8)	0.052 (4)	−0.115 (5)	−0.106 (5)
O5B	0.107 (5)	0.066 (4)	0.076 (4)	0.025 (3)	−0.022 (3)	−0.022 (3)
O6B	0.144 (6)	0.080 (4)	0.0251 (16)	−0.010 (3)	−0.008 (2)	−0.0062 (19)
O7	0.0551 (8)	0.0567 (7)	0.0399 (6)	−0.0104 (6)	−0.0098 (5)	0.0117 (5)
O8	0.0708 (10)	0.0877 (10)	0.0489 (8)	−0.0328 (8)	−0.0119 (6)	0.0194 (7)
C1	0.0458 (9)	0.0473 (9)	0.0344 (8)	−0.0055 (7)	−0.0011 (7)	0.0073 (7)
C2	0.0508 (10)	0.0414 (8)	0.0390 (8)	0.0001 (7)	0.0005 (7)	0.0060 (7)
C3	0.0569 (11)	0.0440 (9)	0.0394 (8)	−0.0039 (7)	−0.0013 (7)	−0.0003 (7)
C4	0.0469 (10)	0.0506 (10)	0.0398 (9)	−0.0033 (7)	−0.0052 (7)	0.0049 (7)
C5	0.0492 (10)	0.0487 (9)	0.0456 (9)	0.0030 (7)	0.0019 (7)	0.0045 (8)
C6	0.0532 (10)	0.0454 (9)	0.0379 (8)	−0.0015 (7)	0.0037 (7)	−0.0008 (7)
C7	0.0515 (10)	0.0521 (9)	0.0333 (8)	−0.0019 (8)	0.0018 (7)	0.0028 (7)
C8	0.0462 (9)	0.0497 (9)	0.0344 (8)	0.0027 (7)	0.0012 (7)	−0.0005 (7)
C9	0.0554 (11)	0.0614 (11)	0.0391 (9)	−0.0068 (8)	−0.0027 (8)	0.0059 (8)
C10	0.0570 (12)	0.0676 (12)	0.0465 (10)	−0.0103 (9)	−0.0055 (8)	−0.0004 (9)
C11	0.0468 (10)	0.0723 (12)	0.0384 (9)	0.0095 (9)	−0.0044 (7)	−0.0026 (8)
C12	0.0543 (11)	0.0598 (11)	0.0396 (9)	0.0112 (8)	0.0005 (7)	0.0073 (8)
C13	0.0510 (10)	0.0497 (9)	0.0399 (9)	0.0038 (7)	0.0019 (7)	0.0026 (7)

Cl1—C11	1.7301 (19)	C2—C3	1.383 (2)
N1—O2	1.197 (2)	C3—C4	1.373 (3)
N1—O1	1.201 (2)	C3—H3	0.9300
N1—C2	1.472 (2)	C4—C5	1.370 (3)
N2—O3	1.210 (2)	C5—C6	1.377 (3)
N2—O4	1.213 (2)	C5—H5	0.9300
N2—C4	1.476 (2)	C7—C8	1.468 (2)
N3—O5A	1.149 (5)	C8—C9	1.391 (3)
N3—O6B	1.159 (6)	C8—C13	1.396 (2)
N3—O6A	1.212 (6)	C9—C10	1.380 (3)
N3—O5B	1.269 (7)	C9—H9	0.9300
N3—C6	1.477 (2)	C10—C11	1.379 (3)
O7—C1	1.369 (2)	C10—H10	0.9300
O7—C7	1.380 (2)	C11—C12	1.381 (3)
O8—C7	1.185 (2)	C12—C13	1.379 (3)
C1—C2	1.392 (2)	C12—H12	0.9300
C1—C6	1.395 (3)	C13—H13	0.9300
O2—N1—O1	123.13 (18)	C4—C5—C6	117.85 (17)
O2—N1—C2	117.33 (18)	C4—C5—H5	121.1
O1—N1—C2	119.51 (17)	C6—C5—H5	121.1
O3—N2—O4	124.39 (18)	C5—C6—C1	122.43 (16)
O3—N2—C4	117.75 (17)	C5—C6—N3	116.64 (16)
O4—N2—C4	117.86 (17)	C1—C6—N3	120.93 (17)
O5A—N3—O6B	105.7 (5)	O8—C7—O7	121.40 (16)
O5A—N3—O6A	122.7 (4)	O8—C7—C8	127.36 (16)
O6B—N3—O5B	124.2 (5)	O7—C7—C8	111.19 (15)
O6A—N3—O5B	111.3 (5)	C9—C8—C13	119.90 (17)
O5A—N3—C6	118.8 (3)	C9—C8—C7	122.85 (16)
O6B—N3—C6	120.1 (4)	C13—C8—C7	117.20 (16)
O6A—N3—C6	118.5 (3)	C10—C9—C8	119.82 (18)
O5B—N3—C6	115.6 (3)	C10—C9—H9	120.1
C1—O7—C7	117.57 (14)	C8—C9—H9	120.1
O7—C1—C2	123.42 (16)	C11—C10—C9	119.50 (19)
O7—C1—C6	119.22 (16)	C11—C10—H10	120.2
C2—C1—C6	117.23 (16)	C9—C10—H10	120.2
C3—C2—C1	121.39 (16)	C10—C11—C12	121.54 (17)
C3—C2—N1	116.22 (16)	C10—C11—Cl1	119.54 (16)
C1—C2—N1	122.31 (16)	C12—C11—Cl1	118.91 (15)
C4—C3—C2	118.59 (17)	C13—C12—C11	119.16 (17)
C4—C3—H3	120.7	C13—C12—H12	120.4
C2—C3—H3	120.7	C11—C12—H12	120.4
C5—C4—C3	122.47 (17)	C12—C13—C8	120.06 (18)
C5—C4—N2	119.06 (16)	C12—C13—H13	120.0
C3—C4—N2	118.47 (16)	C8—C13—H13	120.0
C7—O7—C1—C2	−74.2 (2)	C2—C1—C6—N3	178.57 (16)
C7—O7—C1—C6	109.99 (18)	O5A—N3—C6—C5	28.5 (4)
O7—C1—C2—C3	−175.31 (15)	O6B—N3—C6—C5	161.0 (5)
C6—C1—C2—C3	0.5 (2)	O6A—N3—C6—C5	−152.5 (5)
O7—C1—C2—N1	1.4 (3)	O5B—N3—C6—C5	−16.5 (5)
C6—C1—C2—N1	177.23 (15)	O5A—N3—C6—C1	−151.2 (4)
O2—N1—C2—C3	−12.3 (3)	O6B—N3—C6—C1	−18.8 (5)
O1—N1—C2—C3	165.66 (18)	O6A—N3—C6—C1	27.7 (6)
O2—N1—C2—C1	170.8 (2)	O5B—N3—C6—C1	163.7 (4)
O1—N1—C2—C1	−11.2 (3)	C1—O7—C7—O8	2.2 (3)
C1—C2—C3—C4	1.1 (3)	C1—O7—C7—C8	−175.40 (14)
N1—C2—C3—C4	−175.83 (16)	O8—C7—C8—C9	−170.4 (2)
C2—C3—C4—C5	−2.1 (3)	O7—C7—C8—C9	6.9 (3)
C2—C3—C4—N2	177.22 (16)	O8—C7—C8—C13	7.0 (3)
O3—N2—C4—C5	−178.2 (2)	O7—C7—C8—C13	−175.63 (15)
O4—N2—C4—C5	2.8 (3)	C13—C8—C9—C10	−1.1 (3)
O3—N2—C4—C3	2.4 (3)	C7—C8—C9—C10	176.21 (17)
O4—N2—C4—C3	−176.62 (19)	C8—C9—C10—C11	0.6 (3)
C3—C4—C5—C6	1.5 (3)	C9—C10—C11—C12	0.2 (3)
N2—C4—C5—C6	−177.86 (16)	C9—C10—C11—Cl1	−178.89 (16)
C4—C5—C6—C1	0.2 (3)	C10—C11—C12—C13	−0.5 (3)
C4—C5—C6—N3	−179.55 (17)	Cl1—C11—C12—C13	178.57 (14)
O7—C1—C6—C5	174.83 (15)	C11—C12—C13—C8	0.0 (3)
C2—C1—C6—C5	−1.2 (3)	C9—C8—C13—C12	0.8 (3)
O7—C1—C6—N3	−5.4 (2)	C7—C8—C13—C12	−176.69 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O4i	0.93	2.55	3.472 (3)	174
C5—H5···O8ii	0.93	2.53	3.457 (2)	174
C3—H3···O6Biii	0.93	2.36	3.188 (5)	147
C12—H12···O1iv	0.93	2.51	3.377 (2)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O4i	0.93	2.55	3.472 (3)	174
C5—H5⋯O8ii	0.93	2.53	3.457 (2)	174
C3—H3⋯O6B iii	0.93	2.36	3.188 (5)	147
C12—H12⋯O1iv	0.93	2.51	3.377 (2)	156

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