3,5-Dinitro-benzoyl chloride.

The carbonyl chloride group in the title compound, C(7)H(3)ClN(2)O(5), is disordered over two orientations with occupancies of 0.505 (5) and 0.495 (5). The mol-ecule is approximately planar, the dihedral angle between the carbonyl chloride plane and benzene ring being 9.6 (4)° in the major disorder component and 7.1 (4)° in the minor component. The nitro group at the 5-position is twisted, forming a dihedral angle of 6.7 (4)°. The crystal packing is stabilized by C-H⋯O hydrogen bonds.

Related literature

For general background to 3,5-dinitro­benzoyl chloride, see: Gennaro et al. (1993 ▶); Liu & Wang (2000 ▶); Saunders & Stacey (1942 ▶).

Experimental

Crystal data

C7H3ClN2O5

M = 230.56

Orthorhombic,

a = 18.295 (4) Å

b = 8.3924 (19) Å

c = 5.7362 (13) Å

V = 880.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.44 mm−1

T = 93 K

0.37 × 0.33 × 0.27 mm

Data collection

Rigaku SPIDER diffractometer

Absorption correction: none

6904 measured reflections

2011 independent reflections

1835 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.097

S = 1.03

2011 reflections

164 parameters

29 restraints

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.22 e Å−3

Absolute structure: Flack (1983 ▶), 905 Friedel pairs

Flack parameter: 0.08 (9)

Data collection: RAPID-AUTO (Rigaku 2004 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809036228/ci2867sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809036228/ci2867Isup2.hkl

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

C7H3ClN2O5	F(000) = 464
Mr = 230.56	Dx = 1.739 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2915 reflections
a = 18.295 (4) Å	θ = 3.3–27.5°
b = 8.3924 (19) Å	µ = 0.44 mm−1
c = 5.7362 (13) Å	T = 93 K
V = 880.7 (3) Å3	Block, colourless
Z = 4	0.37 × 0.33 × 0.27 mm

Rigaku SPIDER diffractometer	1835 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.025
graphite	θmax = 27.5°, θmin = 3.3°
ω scans	h = −23→22
6904 measured reflections	k = −10→10
2011 independent reflections	l = −7→7

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)] = 0.038	H-atom parameters constrained
wR(F2) = 0.097	w = 1/[σ2(Fo2) + (0.0626P)2] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
2011 reflections	Δρmax = 0.40 e Å−3
164 parameters	Δρmin = −0.21 e Å−3
29 restraints	Absolute structure: Flack (1983), 905 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.08 (9)

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	Occ. (<1)
Cl1	0.43221 (12)	0.5812 (3)	0.3714 (5)	0.0418 (5)	0.505 (5)
C7	0.3864 (3)	0.4499 (11)	0.5519 (12)	0.0289 (16)	0.505 (5)
O1	0.3635 (5)	0.4892 (13)	0.7358 (18)	0.098 (5)	0.505 (5)
Cl1'	0.37524 (15)	0.5156 (3)	0.7640 (4)	0.0442 (5)	0.495 (5)
C7'	0.4064 (3)	0.4534 (13)	0.4960 (13)	0.035 (2)	0.495 (5)
O1'	0.4432 (5)	0.5374 (11)	0.377 (2)	0.083 (3)	0.495 (5)
C1	0.38140 (12)	0.2885 (3)	0.4413 (4)	0.0325 (5)
C2	0.41455 (11)	0.2335 (3)	0.2394 (4)	0.0324 (5)
H2	0.4468	0.2995	0.1526	0.039*
C3	0.39917 (11)	0.0787 (2)	0.1677 (4)	0.0277 (4)
C4	0.35290 (10)	−0.0199 (2)	0.2878 (4)	0.0276 (4)
H4	0.3428	−0.1251	0.2355	0.033*
C5	0.32173 (11)	0.0400 (2)	0.4872 (4)	0.0288 (4)
C6	0.33439 (11)	0.1924 (2)	0.5677 (4)	0.0320 (5)
H6	0.3115	0.2303	0.7057	0.038*
N1	0.43482 (9)	0.0200 (2)	−0.0448 (3)	0.0308 (4)
N2	0.27342 (10)	−0.0636 (2)	0.6268 (3)	0.0361 (4)
O2	0.47388 (8)	0.10880 (19)	−0.1549 (3)	0.0384 (4)
O3	0.42041 (8)	−0.1304 (2)	−0.1076 (3)	0.0426 (4)
O4	0.25855 (9)	−0.19494 (18)	0.5508 (3)	0.0396 (4)
O5	0.25255 (10)	−0.0136 (3)	0.8142 (4)	0.0579 (6)

	U11	U22	U33	U12	U13	U23
Cl1	0.0443 (8)	0.0269 (9)	0.0541 (9)	−0.0110 (6)	0.0055 (7)	−0.0027 (8)
C7	0.033 (3)	0.026 (2)	0.028 (3)	0.006 (3)	0.003 (3)	−0.008 (3)
O1	0.108 (7)	0.085 (6)	0.100 (7)	0.003 (4)	−0.004 (5)	−0.006 (4)
Cl1'	0.0540 (9)	0.0372 (8)	0.0414 (9)	−0.0016 (7)	0.0034 (7)	0.0000 (8)
C7'	0.029 (3)	0.044 (3)	0.034 (4)	0.001 (3)	0.005 (3)	−0.014 (3)
O1'	0.104 (6)	0.056 (5)	0.088 (5)	−0.021 (4)	0.030 (4)	−0.030 (4)
C1	0.0386 (11)	0.0261 (10)	0.0328 (11)	0.0017 (8)	−0.0118 (9)	−0.0037 (9)
C2	0.0353 (11)	0.0284 (10)	0.0336 (11)	−0.0030 (8)	−0.0078 (9)	0.0027 (10)
C3	0.0295 (10)	0.0283 (10)	0.0253 (10)	0.0033 (7)	−0.0041 (8)	−0.0008 (8)
C4	0.0286 (9)	0.0258 (9)	0.0286 (11)	0.0003 (7)	−0.0061 (8)	−0.0030 (8)
C5	0.0280 (9)	0.0315 (10)	0.0268 (10)	−0.0007 (8)	−0.0032 (8)	−0.0012 (9)
C6	0.0352 (11)	0.0325 (10)	0.0283 (10)	0.0055 (9)	−0.0061 (9)	−0.0048 (9)
N1	0.0333 (9)	0.0310 (9)	0.0281 (9)	0.0011 (7)	−0.0009 (7)	−0.0007 (8)
N2	0.0370 (10)	0.0394 (10)	0.0320 (10)	−0.0078 (8)	0.0004 (9)	−0.0085 (9)
O2	0.0372 (8)	0.0431 (9)	0.0348 (9)	−0.0005 (6)	0.0045 (7)	0.0076 (7)
O3	0.0345 (8)	0.0728 (12)	0.0205 (7)	0.0114 (7)	0.0055 (6)	−0.0008 (9)
O4	0.0452 (9)	0.0383 (8)	0.0355 (8)	−0.0115 (7)	−0.0003 (7)	−0.0075 (7)
O5	0.0665 (12)	0.0637 (13)	0.0435 (12)	−0.0216 (10)	0.0226 (9)	−0.0250 (10)

Cl1—C7	1.728 (8)	C3—N1	1.468 (3)
C7—O1	1.182 (9)	C4—C5	1.374 (3)
C7—C1	1.499 (9)	C4—H4	0.95
Cl1'—C7'	1.720 (9)	C5—C6	1.380 (3)
C7'—O1'	1.190 (8)	C5—N2	1.476 (3)
C7'—C1	1.491 (11)	C6—H6	0.95
C1—C6	1.384 (3)	N1—O2	1.210 (2)
C1—C2	1.387 (3)	N1—O3	1.339 (3)
C2—C3	1.391 (3)	N2—O5	1.216 (3)
C2—H2	0.95	N2—O4	1.216 (2)
C3—C4	1.370 (3)
O1—C7—C1	127.5 (9)	C2—C3—N1	117.96 (19)
O1—C7—Cl1	121.9 (9)	C3—C4—C5	117.00 (19)
C1—C7—Cl1	110.6 (4)	C3—C4—H4	121.5
O1'—C7'—C1	127.1 (9)	C5—C4—H4	121.5
O1'—C7'—Cl1'	121.3 (10)	C4—C5—C6	123.3 (2)
C1—C7'—Cl1'	111.6 (5)	C4—C5—N2	118.99 (18)
C6—C1—C2	121.02 (19)	C6—C5—N2	117.72 (19)
C6—C1—C7'	128.4 (3)	C5—C6—C1	118.0 (2)
C2—C1—C7'	110.5 (3)	C5—C6—H6	121.0
C6—C1—C7	110.1 (3)	C1—C6—H6	121.0
C2—C1—C7	128.9 (3)	O2—N1—O3	123.80 (18)
C1—C2—C3	118.0 (2)	O2—N1—C3	119.29 (18)
C1—C2—H2	121.0	O3—N1—C3	116.89 (16)
C3—C2—H2	121.0	O5—N2—O4	124.1 (2)
C4—C3—C2	122.7 (2)	O5—N2—C5	117.64 (18)
C4—C3—N1	119.31 (18)	O4—N2—C5	118.26 (18)
O1'—C7'—C1—C6	−174.9 (4)	C2—C3—C4—C5	−0.4 (3)
Cl1'—C7'—C1—C6	5.2 (4)	N1—C3—C4—C5	179.13 (17)
O1'—C7'—C1—C2	7.5 (3)	C3—C4—C5—C6	0.6 (3)
Cl1'—C7'—C1—C2	−172.4 (2)	C3—C4—C5—N2	−177.98 (18)
O1'—C7'—C1—C7	−161.7 (9)	C4—C5—C6—C1	−0.6 (3)
Cl1'—C7'—C1—C7	18.3 (8)	N2—C5—C6—C1	178.06 (18)
O1—C7—C1—C6	10.2 (3)	C2—C1—C6—C5	0.3 (3)
Cl1—C7—C1—C6	−169.9 (2)	C7'—C1—C6—C5	−177.1 (3)
O1—C7—C1—C2	−171.9 (4)	C7—C1—C6—C5	178.4 (2)
Cl1—C7—C1—C2	8.1 (4)	C4—C3—N1—O2	177.70 (19)
O1—C7—C1—C7'	−158.9 (9)	C2—C3—N1—O2	−2.7 (3)
Cl1—C7—C1—C7'	21.1 (8)	C4—C3—N1—O3	−1.0 (3)
C6—C1—C2—C3	0.0 (3)	C2—C3—N1—O3	178.60 (18)
C7'—C1—C2—C3	177.8 (2)	C4—C5—N2—O5	172.6 (2)
C7—C1—C2—C3	−177.8 (3)	C6—C5—N2—O5	−6.1 (3)
C1—C2—C3—C4	0.1 (3)	C4—C5—N2—O4	−5.4 (3)
C1—C2—C3—N1	−179.43 (17)	C6—C5—N2—O4	175.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O4i	0.95	2.44	3.386 (3)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O4i	0.95	2.44	3.386 (3)	173

Symmetry code: (i) .