4-Nitro-N-(3-nitro-phen-yl)benzamide.

The title compound, C(13)H(9)N(3)O(5), prepared as a solid derivative of 3-nitro-analine via reaction with 4-nitro-benzoyl chloride, crystallizes in a chiral space group. The mol-ecule is non-planar with a dihedral angle of 26.1 (1)° between the two benzene rings. Both nitro groups are twisted slightly out of the plane of their corresponding benzene rings, making dihedral angles of 10.7 (4) and 13.5 (4)°. The mol-ecules are stacked along the a axis with benzene ring centroid-centroid distances of 3.8878 (6) Å. In the crystal, inter-molecular benzene C-H⋯O inter-actions involving one nitro group and the carbonyl group link the mol-ecules, forming chains along [001]. An additional set of aromatic C-H⋯O inter-actions with the second nitro group form chains along [101], connecting adjacent chains to create layers perpendicular to the b axis.

Related literature

For the preparation, properties and applications of the title compound, see: Kichitaro (1954 ▶); Shchel’tsyn et al. (1972 ▶); Kang et al. (2008 ▶). For related structures, see: Hariharan & Srinivasan (1990 ▶); Adams et al. (2001 ▶); Novozhilova et al. (1986 ▶); Sun et al. (2009 ▶). The title compound represents a relatively unusual example of an achiral mol­ecule in a chiral (Sohncke) space group with the conformational flexibility to convert to its mirror image (Pidcock, 2005 ▶).

Experimental

Crystal data

C13H9N3O5

M = 287.23

Monoclinic,

a = 3.8878 (6) Å

b = 21.686 (3) Å

c = 7.3919 (11) Å

β = 90.294 (11)°

V = 623.20 (16) Å3

Z = 2

Mo Kα radiation

μ = 0.12 mm−1

T = 200 K

0.45 × 0.20 × 0.12 mm

Data collection

Bruker SMART X2S benchtop diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.737, T max = 0.989

3940 measured reflections

1136 independent reflections

1008 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.083

S = 1.07

1136 reflections

190 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 and GIS (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) and OLEX2 (Dolomanov et al., 2009 ▶); molecular graphics: PLATON (Spek, 2009 ▶), Mercury (Macrae et al., 2008 ▶), and POV-RAY (Cason, 2004 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811038062/zl2389sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811038062/zl2389Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811038062/zl2389Isup3.mol

Supplementary material file. DOI: 10.1107/S1600536811038062/zl2389Isup4.cml

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

C13H9N3O5	Dx = 1.531 Mg m−3
Mr = 287.23	Melting point: 502 K
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 3.8878 (6) Å	Cell parameters from 1373 reflections
b = 21.686 (3) Å	θ = 2.8–24.6°
c = 7.3919 (11) Å	µ = 0.12 mm−1
β = 90.294 (11)°	T = 200 K
V = 623.20 (16) Å3	Block, clear colourless
Z = 2	0.45 × 0.20 × 0.12 mm
F(000) = 296

Bruker SMART X2S benchtop diffractometer	1136 independent reflections
Radiation source: fine-focus sealed tube	1008 reflections with I > 2σ(I)
doubly curved silicon crystal	Rint = 0.032
Detector resolution: 8.3330 pixels mm-1	θmax = 25.1°, θmin = 2.8°
ω scans	h = −4→3
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −25→25
Tmin = 0.737, Tmax = 0.989	l = −8→8
3940 measured reflections

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)] = 0.034	Hydrogen site location: difference Fourier map
wR(F2) = 0.083	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.046P)2 + 0.048P] where P = (Fo2 + 2Fc2)/3
1136 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.13 e Å−3
1 restraint	Δρmin = −0.17 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
C1	0.5757 (8)	0.50143 (14)	0.7761 (4)	0.0293 (7)
C2	0.4065 (8)	0.55485 (16)	0.8360 (4)	0.0342 (8)
H2	0.3754	0.5616	0.9618	0.041*
C3	0.2833 (8)	0.59829 (15)	0.7109 (4)	0.0335 (7)
H3	0.1647	0.6342	0.7499	0.040*
C4	0.3402 (8)	0.58731 (15)	0.5270 (4)	0.0305 (7)
C5	0.5099 (8)	0.53518 (14)	0.4631 (4)	0.0324 (7)
H5	0.5439	0.5292	0.3372	0.039*
C6	0.6291 (8)	0.49190 (14)	0.5889 (4)	0.0310 (7)
H6	0.7462	0.4560	0.5487	0.037*
N1	0.2079 (8)	0.63348 (12)	0.3938 (4)	0.0376 (7)
O1	0.3012 (8)	0.62833 (13)	0.2344 (3)	0.0634 (9)
O2	0.0141 (7)	0.67441 (11)	0.4478 (3)	0.0505 (7)
C7	0.7131 (8)	0.45847 (15)	0.9221 (4)	0.0331 (7)
O3	0.7597 (8)	0.47773 (12)	1.0776 (3)	0.0533 (7)
N2	0.7873 (7)	0.39887 (12)	0.8706 (3)	0.0333 (6)
H2N	0.7336	0.3889	0.7585	0.040*
C8	0.9407 (8)	0.35147 (14)	0.9776 (4)	0.0288 (7)
C9	1.0551 (8)	0.36141 (15)	1.1561 (4)	0.0300 (7)
H9	1.0295	0.4004	1.2133	0.036*
C10	1.2070 (8)	0.31193 (15)	1.2457 (4)	0.0293 (7)
C11	1.2552 (8)	0.25372 (14)	1.1709 (4)	0.0317 (7)
H11	1.3622	0.2214	1.2371	0.038*
C12	1.1382 (9)	0.24514 (16)	0.9931 (4)	0.0352 (8)
H12	1.1654	0.2061	0.9368	0.042*
C13	0.9830 (8)	0.29302 (14)	0.8981 (4)	0.0318 (7)
H13	0.9045	0.2862	0.7778	0.038*
N3	1.3347 (7)	0.32240 (13)	1.4340 (3)	0.0344 (6)
O4	1.2424 (7)	0.36973 (11)	1.5145 (3)	0.0508 (7)
O5	1.5281 (7)	0.28377 (13)	1.5016 (3)	0.0543 (8)

	U11	U22	U33	U12	U13	U23
C1	0.0323 (17)	0.0299 (17)	0.0255 (14)	−0.0032 (15)	−0.0023 (13)	0.0021 (12)
C2	0.0383 (18)	0.0392 (19)	0.0253 (14)	0.0005 (16)	0.0027 (13)	−0.0022 (13)
C3	0.0303 (17)	0.0330 (18)	0.0371 (17)	0.0016 (15)	0.0012 (13)	−0.0011 (14)
C4	0.0320 (16)	0.0287 (17)	0.0308 (16)	−0.0020 (14)	−0.0026 (12)	0.0035 (13)
C5	0.0403 (18)	0.0312 (18)	0.0257 (15)	−0.0023 (15)	−0.0015 (13)	−0.0001 (13)
C6	0.0346 (18)	0.0283 (17)	0.0301 (15)	0.0007 (14)	0.0000 (13)	−0.0031 (12)
N1	0.0463 (18)	0.0298 (15)	0.0367 (15)	0.0001 (14)	−0.0049 (13)	0.0033 (13)
O1	0.099 (2)	0.0583 (19)	0.0333 (14)	0.0236 (17)	0.0009 (14)	0.0090 (13)
O2	0.0610 (17)	0.0369 (15)	0.0537 (15)	0.0135 (14)	0.0044 (13)	0.0066 (12)
C7	0.0341 (18)	0.037 (2)	0.0277 (16)	0.0001 (15)	0.0005 (13)	−0.0016 (13)
O3	0.085 (2)	0.0503 (15)	0.0244 (12)	0.0198 (15)	−0.0099 (12)	−0.0062 (11)
N2	0.0453 (16)	0.0324 (15)	0.0220 (12)	−0.0026 (13)	−0.0077 (11)	0.0010 (11)
C8	0.0286 (17)	0.0346 (18)	0.0233 (14)	−0.0032 (14)	0.0019 (12)	0.0037 (12)
C9	0.0314 (17)	0.0344 (18)	0.0240 (15)	−0.0012 (14)	−0.0021 (12)	0.0000 (13)
C10	0.0269 (17)	0.0427 (18)	0.0182 (12)	−0.0047 (14)	−0.0033 (12)	0.0011 (13)
C11	0.0304 (17)	0.0335 (19)	0.0312 (16)	0.0005 (15)	−0.0003 (13)	0.0033 (14)
C12	0.0384 (19)	0.0336 (18)	0.0337 (16)	0.0003 (15)	0.0013 (14)	−0.0027 (14)
C13	0.0346 (18)	0.0376 (18)	0.0232 (14)	−0.0045 (15)	−0.0032 (13)	−0.0017 (13)
N3	0.0336 (15)	0.0445 (18)	0.0251 (12)	−0.0069 (14)	−0.0066 (11)	0.0053 (13)
O4	0.0796 (19)	0.0431 (15)	0.0297 (12)	−0.0025 (14)	−0.0110 (12)	−0.0067 (11)
O5	0.0541 (16)	0.0731 (19)	0.0356 (12)	0.0159 (15)	−0.0163 (11)	0.0044 (13)

C1—C2	1.405 (5)	N2—C8	1.426 (4)
C1—C6	1.415 (4)	N2—H2N	0.8800
C1—C7	1.520 (4)	C8—C13	1.407 (4)
C2—C3	1.403 (4)	C8—C9	1.407 (4)
C2—H2	0.9500	C9—C10	1.391 (4)
C3—C4	1.399 (4)	C9—H9	0.9500
C3—H3	0.9500	C10—C11	1.391 (4)
C4—C5	1.393 (4)	C10—N3	1.493 (4)
C4—N1	1.494 (4)	C11—C12	1.401 (4)
C5—C6	1.398 (4)	C11—H11	0.9500
C5—H5	0.9500	C12—C13	1.390 (4)
C6—H6	0.9500	C12—H12	0.9500
N1—O2	1.232 (4)	C13—H13	0.9500
N1—O1	1.240 (4)	N3—O5	1.230 (3)
C7—O3	1.235 (4)	N3—O4	1.240 (4)
C7—N2	1.378 (4)
C2—C1—C6	120.0 (3)	C7—N2—C8	127.6 (3)
C2—C1—C7	116.4 (2)	C7—N2—H2N	116.2
C6—C1—C7	123.5 (3)	C8—N2—H2N	116.2
C3—C2—C1	120.3 (3)	C13—C8—C9	119.5 (3)
C3—C2—H2	119.8	C13—C8—N2	117.9 (2)
C1—C2—H2	119.8	C9—C8—N2	122.6 (3)
C4—C3—C2	118.1 (3)	C10—C9—C8	117.4 (3)
C4—C3—H3	120.9	C10—C9—H9	121.3
C2—C3—H3	120.9	C8—C9—H9	121.3
C5—C4—C3	123.0 (3)	C9—C10—C11	124.7 (2)
C5—C4—N1	118.9 (2)	C9—C10—N3	117.7 (3)
C3—C4—N1	118.1 (3)	C11—C10—N3	117.6 (3)
C4—C5—C6	118.4 (3)	C10—C11—C12	116.7 (3)
C4—C5—H5	120.8	C10—C11—H11	121.6
C6—C5—H5	120.8	C12—C11—H11	121.6
C5—C6—C1	120.2 (3)	C13—C12—C11	120.9 (3)
C5—C6—H6	119.9	C13—C12—H12	119.6
C1—C6—H6	119.9	C11—C12—H12	119.6
O2—N1—O1	123.7 (3)	C12—C13—C8	120.9 (3)
O2—N1—C4	118.6 (3)	C12—C13—H13	119.6
O1—N1—C4	117.7 (3)	C8—C13—H13	119.6
O3—C7—N2	123.0 (3)	O5—N3—O4	123.1 (3)
O3—C7—C1	120.2 (3)	O5—N3—C10	118.4 (3)
N2—C7—C1	116.8 (3)	O4—N3—C10	118.5 (3)
C6—C1—C2—C3	1.4 (4)	O3—C7—N2—C8	−3.5 (5)
C7—C1—C2—C3	177.5 (3)	C1—C7—N2—C8	175.1 (3)
C1—C2—C3—C4	−1.2 (5)	C7—N2—C8—C13	178.0 (3)
C2—C3—C4—C5	0.6 (5)	C7—N2—C8—C9	−3.1 (5)
C2—C3—C4—N1	179.8 (3)	C13—C8—C9—C10	0.1 (4)
C3—C4—C5—C6	−0.1 (5)	N2—C8—C9—C10	−178.7 (3)
N1—C4—C5—C6	−179.3 (3)	C8—C9—C10—C11	0.4 (4)
C4—C5—C6—C1	0.2 (5)	C8—C9—C10—N3	178.9 (3)
C2—C1—C6—C5	−0.8 (5)	C9—C10—C11—C12	−0.5 (4)
C7—C1—C6—C5	−176.7 (3)	N3—C10—C11—C12	−179.0 (3)
C5—C4—N1—O2	169.1 (3)	C10—C11—C12—C13	0.2 (5)
C3—C4—N1—O2	−10.1 (4)	C11—C12—C13—C8	0.3 (5)
C5—C4—N1—O1	−11.0 (4)	C9—C8—C13—C12	−0.4 (5)
C3—C4—N1—O1	169.8 (3)	N2—C8—C13—C12	178.4 (3)
C2—C1—C7—O3	−19.7 (5)	C9—C10—N3—O5	−165.8 (3)
C6—C1—C7—O3	156.3 (3)	C11—C10—N3—O5	12.8 (4)
C2—C1—C7—N2	161.6 (3)	C9—C10—N3—O4	13.9 (4)
C6—C1—C7—N2	−22.4 (4)	C11—C10—N3—O4	−167.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1i	0.95	2.50	3.375 (4)	153.
C5—H5···O3ii	0.95	2.38	3.263 (4)	155.
C13—H13···O5iii	0.95	2.51	3.421 (4)	162.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1i	0.95	2.50	3.375 (4)	153
C5—H5⋯O3ii	0.95	2.38	3.263 (4)	155
C13—H13⋯O5iii	0.95	2.51	3.421 (4)	162

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