3,5-Dinitro-N-(4-nitro-phen-yl)benzamide.

In the title mol-ecule, C(13)H(8)N(4)O(7), the amide fragment has an anti configuration. The mean planes of the two benzene rings form a dihedral angle of 7.78 (4)°. The mean planes of the three nitro groups are twisted by 6.82 (3), 5.01 (4) and 18.94 (7)° with respect to the benzene rings to which they are attached. In the crystal, mol-ecules are linked by weak inter-molecular N-H⋯O hydrogen bonds into chains along [100].

Related literature

For background to the biological activity of N-substituted benzamides and their use in synthesis, see: Saeed et al. (2010 ▶). For related structures, see: Raza et al. (2010 ▶); Gowda et al. (2003 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C13H8N4O7

M = 332.23

Monoclinic,

a = 7.8999 (9) Å

b = 8.019 (1) Å

c = 21.111 (2) Å

β = 94.285 (1)°

V = 1333.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.14 mm−1

T = 298 K

0.48 × 0.38 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.937, T max = 0.980

6462 measured reflections

2361 independent reflections

1419 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.127

S = 1.01

2361 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810045915/lh5155sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045915/lh5155Isup2.hkl

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

C13H8N4O7	F(000) = 680
Mr = 332.23	Dx = 1.655 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1593 reflections
a = 7.8999 (9) Å	θ = 2.6–26.4°
b = 8.019 (1) Å	µ = 0.14 mm−1
c = 21.111 (2) Å	T = 298 K
β = 94.285 (1)°	Plate, colorless
V = 1333.7 (3) Å3	0.48 × 0.38 × 0.15 mm
Z = 4

Bruker SMART CCD diffractometer	2361 independent reflections
Radiation source: fine-focus sealed tube	1419 reflections with I > 2σ(I)
graphite	Rint = 0.055
φ and ω scans	θmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.937, Tmax = 0.980	k = −9→9
6462 measured reflections	l = −25→17

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) = 0.127	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0524P)2 + 0.2955P] where P = (Fo2 + 2Fc2)/3
2361 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.22 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
N1	1.4744 (2)	0.3431 (3)	0.43550 (9)	0.0417 (6)
H1	1.5292	0.3850	0.4056	0.050*
N2	0.8118 (3)	0.6627 (3)	0.33003 (12)	0.0470 (6)
N3	1.3396 (3)	0.6676 (4)	0.22261 (10)	0.0503 (7)
N4	1.8925 (3)	0.0058 (3)	0.61994 (11)	0.0498 (7)
O1	1.2103 (2)	0.3154 (3)	0.46823 (9)	0.0623 (7)
O2	0.7337 (2)	0.6051 (3)	0.37295 (10)	0.0605 (6)
O3	0.7509 (3)	0.7558 (3)	0.28922 (11)	0.0735 (8)
O4	1.2863 (3)	0.7866 (3)	0.19062 (10)	0.0702 (7)
O5	1.4673 (3)	0.5907 (3)	0.21316 (9)	0.0737 (8)
O6	2.0458 (3)	0.0098 (3)	0.61510 (10)	0.0680 (7)
O7	1.8282 (3)	−0.0657 (4)	0.66238 (11)	0.0845 (9)
C1	1.3044 (3)	0.3678 (3)	0.43039 (12)	0.0381 (7)
C2	1.2337 (3)	0.4698 (3)	0.37448 (11)	0.0340 (6)
C3	1.0657 (3)	0.5183 (3)	0.37588 (12)	0.0376 (7)
H3	1.0034	0.4865	0.4096	0.045*
C4	0.9913 (3)	0.6136 (3)	0.32735 (12)	0.0362 (6)
C5	1.0782 (3)	0.6669 (3)	0.27726 (11)	0.0385 (7)
H5	1.0272	0.7341	0.2454	0.046*
C6	1.2440 (3)	0.6163 (3)	0.27634 (11)	0.0359 (6)
C7	1.3229 (3)	0.5177 (3)	0.32335 (11)	0.0374 (7)
H7	1.4347	0.4837	0.3207	0.045*
C8	1.5729 (3)	0.2579 (3)	0.48343 (11)	0.0343 (6)
C9	1.7451 (3)	0.2441 (4)	0.47600 (13)	0.0434 (7)
H9	1.7894	0.2898	0.4403	0.052*
C10	1.8513 (3)	0.1638 (4)	0.52054 (12)	0.0441 (7)
H10	1.9671	0.1561	0.5157	0.053*
C11	1.7825 (3)	0.0952 (3)	0.57246 (12)	0.0374 (7)
C12	1.6121 (3)	0.1071 (4)	0.58118 (12)	0.0419 (7)
H12	1.5688	0.0596	0.6168	0.050*
C13	1.5060 (3)	0.1896 (4)	0.53691 (11)	0.0413 (7)
H13	1.3908	0.1997	0.5426	0.050*

	U11	U22	U33	U12	U13	U23
N1	0.0368 (12)	0.0543 (17)	0.0345 (12)	0.0023 (11)	0.0061 (9)	0.0137 (11)
N2	0.0389 (13)	0.0526 (18)	0.0483 (15)	0.0044 (12)	−0.0050 (11)	−0.0092 (13)
N3	0.0473 (15)	0.071 (2)	0.0325 (14)	−0.0119 (14)	0.0026 (11)	−0.0005 (14)
N4	0.0538 (16)	0.0493 (18)	0.0445 (15)	0.0019 (13)	−0.0091 (12)	0.0000 (12)
O1	0.0413 (11)	0.0895 (18)	0.0571 (13)	0.0032 (11)	0.0099 (10)	0.0337 (13)
O2	0.0436 (11)	0.0765 (17)	0.0632 (14)	0.0030 (11)	0.0155 (10)	−0.0032 (12)
O3	0.0575 (14)	0.091 (2)	0.0701 (16)	0.0252 (13)	−0.0085 (11)	0.0178 (14)
O4	0.0778 (16)	0.0818 (19)	0.0513 (14)	−0.0048 (14)	0.0066 (11)	0.0273 (13)
O5	0.0576 (14)	0.112 (2)	0.0538 (14)	0.0055 (14)	0.0224 (11)	0.0070 (13)
O6	0.0534 (14)	0.0822 (19)	0.0665 (15)	0.0147 (12)	−0.0085 (11)	0.0043 (12)
O7	0.0761 (16)	0.112 (2)	0.0634 (16)	−0.0021 (15)	−0.0101 (12)	0.0486 (15)
C1	0.0375 (15)	0.0405 (18)	0.0362 (15)	−0.0014 (13)	0.0024 (12)	0.0030 (13)
C2	0.0344 (14)	0.0354 (17)	0.0318 (14)	−0.0021 (12)	0.0007 (11)	−0.0007 (12)
C3	0.0366 (14)	0.0404 (18)	0.0359 (15)	−0.0042 (13)	0.0028 (11)	−0.0008 (13)
C4	0.0303 (13)	0.0412 (18)	0.0365 (15)	0.0007 (12)	−0.0025 (11)	−0.0056 (13)
C5	0.0418 (15)	0.0427 (18)	0.0298 (15)	−0.0015 (13)	−0.0060 (11)	−0.0019 (13)
C6	0.0390 (15)	0.0422 (18)	0.0267 (14)	−0.0065 (13)	0.0029 (11)	−0.0010 (12)
C7	0.0332 (13)	0.0425 (18)	0.0360 (15)	−0.0037 (12)	0.0006 (11)	−0.0061 (13)
C8	0.0388 (15)	0.0339 (17)	0.0298 (14)	0.0015 (12)	0.0004 (11)	0.0033 (12)
C9	0.0429 (16)	0.051 (2)	0.0373 (15)	0.0016 (13)	0.0080 (12)	0.0113 (13)
C10	0.0410 (15)	0.049 (2)	0.0419 (16)	0.0017 (14)	0.0003 (12)	0.0015 (14)
C11	0.0434 (15)	0.0331 (17)	0.0342 (15)	0.0018 (12)	−0.0070 (12)	−0.0017 (12)
C12	0.0497 (17)	0.0460 (19)	0.0300 (15)	−0.0038 (14)	0.0029 (12)	0.0044 (13)
C13	0.0401 (15)	0.0472 (19)	0.0366 (15)	0.0004 (13)	0.0037 (12)	0.0018 (14)

N1—C1	1.354 (3)	C3—H3	0.9300
N1—C8	1.407 (3)	C4—C5	1.371 (3)
N1—H1	0.8600	C5—C6	1.373 (3)
N2—O3	1.212 (3)	C5—H5	0.9300
N2—O2	1.224 (3)	C6—C7	1.381 (3)
N2—C4	1.476 (3)	C7—H7	0.9300
N3—O5	1.212 (3)	C8—C9	1.385 (3)
N3—O4	1.225 (3)	C8—C13	1.394 (3)
N3—C6	1.467 (3)	C9—C10	1.373 (4)
N4—O7	1.207 (3)	C9—H9	0.9300
N4—O6	1.224 (3)	C10—C11	1.374 (3)
N4—C11	1.464 (3)	C10—H10	0.9300
O1—C1	1.206 (3)	C11—C12	1.376 (3)
C1—C2	1.509 (3)	C12—C13	1.377 (3)
C2—C3	1.386 (3)	C12—H12	0.9300
C2—C7	1.386 (3)	C13—H13	0.9300
C3—C4	1.375 (4)
C1—N1—C8	128.3 (2)	C6—C5—H5	121.5
C1—N1—H1	115.8	C5—C6—C7	122.6 (2)
C8—N1—H1	115.8	C5—C6—N3	118.3 (2)
O3—N2—O2	124.3 (2)	C7—C6—N3	119.1 (2)
O3—N2—C4	117.9 (2)	C6—C7—C2	119.4 (2)
O2—N2—C4	117.8 (2)	C6—C7—H7	120.3
O5—N3—O4	124.2 (2)	C2—C7—H7	120.3
O5—N3—C6	117.9 (3)	C9—C8—C13	119.7 (2)
O4—N3—C6	118.0 (3)	C9—C8—N1	116.9 (2)
O7—N4—O6	123.2 (2)	C13—C8—N1	123.4 (2)
O7—N4—C11	118.7 (2)	C10—C9—C8	121.0 (2)
O6—N4—C11	118.1 (2)	C10—C9—H9	119.5
O1—C1—N1	123.6 (2)	C8—C9—H9	119.5
O1—C1—C2	119.8 (2)	C9—C10—C11	118.4 (2)
N1—C1—C2	116.6 (2)	C9—C10—H10	120.8
C3—C2—C7	118.8 (2)	C11—C10—H10	120.8
C3—C2—C1	115.8 (2)	C10—C11—C12	121.9 (2)
C7—C2—C1	125.4 (2)	C10—C11—N4	119.5 (2)
C4—C3—C2	119.8 (2)	C12—C11—N4	118.6 (2)
C4—C3—H3	120.1	C11—C12—C13	119.6 (2)
C2—C3—H3	120.1	C11—C12—H12	120.2
C5—C4—C3	122.5 (2)	C13—C12—H12	120.2
C5—C4—N2	119.0 (2)	C12—C13—C8	119.3 (2)
C3—C4—N2	118.6 (2)	C12—C13—H13	120.3
C4—C5—C6	116.9 (2)	C8—C13—H13	120.3
C4—C5—H5	121.5
C8—N1—C1—O1	−0.7 (5)	O4—N3—C6—C7	−161.6 (3)
C8—N1—C1—C2	178.0 (2)	C5—C6—C7—C2	−1.4 (4)
O1—C1—C2—C3	9.6 (4)	N3—C6—C7—C2	179.6 (2)
N1—C1—C2—C3	−169.1 (2)	C3—C2—C7—C6	2.0 (4)
O1—C1—C2—C7	−170.7 (3)	C1—C2—C7—C6	−177.7 (2)
N1—C1—C2—C7	10.6 (4)	C1—N1—C8—C9	177.2 (3)
C7—C2—C3—C4	−0.6 (4)	C1—N1—C8—C13	−3.2 (4)
C1—C2—C3—C4	179.1 (2)	C13—C8—C9—C10	0.0 (4)
C2—C3—C4—C5	−1.4 (4)	N1—C8—C9—C10	179.6 (3)
C2—C3—C4—N2	179.7 (2)	C8—C9—C10—C11	0.9 (4)
O3—N2—C4—C5	−3.8 (4)	C9—C10—C11—C12	−1.0 (4)
O2—N2—C4—C5	175.4 (2)	C9—C10—C11—N4	178.7 (3)
O3—N2—C4—C3	175.2 (3)	O7—N4—C11—C10	−173.8 (3)
O2—N2—C4—C3	−5.6 (4)	O6—N4—C11—C10	7.4 (4)
C3—C4—C5—C6	1.9 (4)	O7—N4—C11—C12	5.8 (4)
N2—C4—C5—C6	−179.1 (2)	O6—N4—C11—C12	−173.0 (2)
C4—C5—C6—C7	−0.5 (4)	C10—C11—C12—C13	0.1 (4)
C4—C5—C6—N3	178.5 (2)	N4—C11—C12—C13	−179.6 (3)
O5—N3—C6—C5	−161.5 (3)	C11—C12—C13—C8	0.9 (4)
O4—N3—C6—C5	19.3 (4)	C9—C8—C13—C12	−0.9 (4)
O5—N3—C6—C7	17.5 (4)	N1—C8—C13—C12	179.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.86	2.52	3.280 (3)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.86	2.52	3.280 (3)	147

Symmetry code: (i) .