4-Nitro-N-(4-nitro-benzo-yl)benzamide.

The central acetyl-acetamide moiety in the title compound, C(14)H(9)N(3)O(6), is buckled [e.g. the C-N-C-O torsion angle is 14.3 (6)°] but the r.m.s. deviation for the five atoms is 0.044 Å. The benzene rings lie on the same side of the central plane, forming dihedral angles of 37.17 (15) and 28.58 (19)° with it. The dihedral angle between the two rings is 17.8 (2)° indicating that the mol-ecule is curved. The carbonyl groups are syn to each other and anti to the amino H atom. This allows for the formation of N-H⋯O hydrogen bonds in the crystal, which leads to twisted chains along the b axis. Positional disorder (50:50) of the O atoms was modelled for both the nitro groups.

Related literature

For background to high-temperature polymers for replacement of ceramics and metals, see: Ataei et al. (2005 ▶); Im & Jung, (2000 ▶); Yang et al. (2002 ▶).

Experimental

Crystal data

C14H9N3O6

M = 315.24

Orthorhombic,

a = 13.4757 (7) Å

b = 8.5170 (6) Å

c = 24.6285 (17) Å

V = 2826.7 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.12 mm−1

T = 295 K

0.30 × 0.15 × 0.05 mm

Data collection

Agilent Technologies SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.965, T max = 0.994

13745 measured reflections

2487 independent reflections

1433 reflections with I > 2σ(I)

R int = 0.067

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.217

S = 1.02

2487 reflections

221 parameters

40 restraints

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.31 e Å−3

Data collection: CrysAlis PRO (Agilent, 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 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811014450/hb5852sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811014450/hb5852Isup2.hkl

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

C14H9N3O6	F(000) = 1296
Mr = 315.24	Dx = 1.482 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2137 reflections
a = 13.4757 (7) Å	θ = 2.4–29.3°
b = 8.5170 (6) Å	µ = 0.12 mm−1
c = 24.6285 (17) Å	T = 295 K
V = 2826.7 (3) Å3	Prism, colorless
Z = 8	0.30 × 0.15 × 0.05 mm

Agilent Technologies SuperNova Dual diffractometer with an Atlas detector	2487 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1433 reflections with I > 2σ(I)
Mirror	Rint = 0.067
Detector resolution: 10.4041 pixels mm-1	θmax = 25.1°, θmin = 3.0°
ω scans	h = −16→16
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −10→8
Tmin = 0.965, Tmax = 0.994	l = −29→29
13745 measured reflections

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)] = 0.065	H-atom parameters constrained
wR(F2) = 0.217	w = 1/[σ2(Fo2) + (0.0936P)2 + 1.8503P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
2487 reflections	Δρmax = 0.38 e Å−3
221 parameters	Δρmin = −0.31 e Å−3
40 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: 0.0036 (11)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.975 (3)	0.868 (3)	0.4716 (10)	0.092 (4)	0.50
O2	1.1108 (6)	0.774 (4)	0.5041 (14)	0.087 (3)	0.50
O1'	0.974 (3)	0.835 (3)	0.4633 (9)	0.092 (4)	0.50
O2'	1.1072 (6)	0.804 (4)	0.5128 (14)	0.087 (3)	0.50
O3	0.84634 (19)	0.2233 (3)	0.64513 (11)	0.0615 (8)
O4	0.67456 (19)	0.1707 (3)	0.70172 (11)	0.0596 (8)
O5	0.1877 (10)	0.4334 (12)	0.7162 (4)	0.100 (3)	0.50
O6	0.2086 (12)	0.5041 (11)	0.6323 (4)	0.112 (3)	0.50
O5'	0.1823 (10)	0.3657 (12)	0.6995 (4)	0.100 (3)	0.50
O6'	0.2166 (12)	0.5728 (10)	0.6491 (4)	0.112 (3)	0.50
N1	1.0204 (3)	0.7784 (4)	0.50161 (13)	0.0710 (11)
N2	0.71486 (19)	0.3916 (4)	0.65368 (12)	0.0489 (8)
H2	0.6951	0.4882	0.6471	0.059*
N3	0.2410 (3)	0.4541 (4)	0.67600 (15)	0.0986 (15)
C1	0.8597 (2)	0.4671 (4)	0.60108 (14)	0.0462 (9)
C2	0.9620 (3)	0.4820 (5)	0.60666 (15)	0.0518 (10)
H2A	0.9955	0.4218	0.6323	0.062*
C3	1.0139 (3)	0.5855 (5)	0.57437 (15)	0.0524 (10)
H3	1.0821	0.5976	0.5784	0.063*
C4	0.9630 (3)	0.6702 (4)	0.53628 (14)	0.0525 (10)
C5	0.8623 (3)	0.6587 (5)	0.52915 (15)	0.0576 (11)
H5	0.8299	0.7174	0.5027	0.069*
C6	0.8110 (3)	0.5574 (5)	0.56230 (15)	0.0546 (10)
H6	0.7425	0.5492	0.5587	0.066*
C7	0.8080 (3)	0.3493 (4)	0.63559 (15)	0.0468 (9)
C8	0.6499 (3)	0.2939 (5)	0.68146 (14)	0.0475 (9)
C9	0.5444 (2)	0.3483 (4)	0.68244 (14)	0.0458 (9)
C10	0.4802 (3)	0.2851 (5)	0.72057 (15)	0.0578 (11)
H10	0.5048	0.2180	0.7471	0.069*
C11	0.3815 (3)	0.3200 (6)	0.71968 (17)	0.0691 (13)
H11	0.3385	0.2783	0.7454	0.083*
C12	0.3472 (3)	0.4188 (5)	0.67959 (17)	0.0628 (11)
C13	0.4080 (3)	0.4851 (5)	0.64193 (17)	0.0628 (11)
H13	0.3828	0.5532	0.6158	0.075*
C14	0.5079 (3)	0.4492 (5)	0.64323 (15)	0.0532 (10)
H14	0.5507	0.4929	0.6177	0.064*

	U11	U22	U33	U12	U13	U23
O1	0.125 (3)	0.080 (8)	0.071 (6)	−0.005 (6)	0.007 (5)	0.026 (5)
O2	0.083 (2)	0.087 (9)	0.093 (8)	−0.014 (2)	0.032 (3)	0.006 (5)
O1'	0.125 (3)	0.080 (8)	0.071 (6)	−0.005 (6)	0.007 (5)	0.026 (5)
O2'	0.083 (2)	0.087 (9)	0.093 (8)	−0.014 (2)	0.032 (3)	0.006 (5)
O3	0.0501 (15)	0.0421 (17)	0.092 (2)	0.0075 (12)	0.0066 (14)	0.0080 (14)
O4	0.0601 (17)	0.0487 (17)	0.0699 (17)	0.0045 (13)	0.0018 (13)	0.0090 (14)
O5	0.059 (2)	0.131 (8)	0.109 (6)	0.003 (5)	0.022 (4)	0.021 (5)
O6	0.066 (3)	0.164 (7)	0.105 (5)	0.017 (6)	−0.015 (4)	0.031 (5)
O5'	0.059 (2)	0.131 (8)	0.109 (6)	0.003 (5)	0.022 (4)	0.021 (5)
O6'	0.066 (3)	0.164 (7)	0.105 (5)	0.017 (6)	−0.015 (4)	0.031 (5)
N1	0.088 (3)	0.064 (3)	0.061 (2)	−0.001 (2)	0.018 (2)	0.007 (2)
N2	0.0411 (16)	0.0393 (18)	0.066 (2)	0.0004 (14)	0.0043 (14)	0.0044 (15)
N3	0.054 (2)	0.150 (4)	0.091 (3)	0.011 (3)	0.005 (2)	0.040 (3)
C1	0.045 (2)	0.043 (2)	0.051 (2)	0.0012 (16)	0.0009 (16)	−0.0034 (17)
C2	0.047 (2)	0.055 (2)	0.053 (2)	0.0058 (18)	−0.0012 (17)	0.0064 (19)
C3	0.047 (2)	0.055 (2)	0.055 (2)	−0.0038 (18)	0.0067 (18)	−0.0019 (19)
C4	0.063 (3)	0.049 (2)	0.045 (2)	−0.0002 (19)	0.0097 (18)	0.0019 (18)
C5	0.065 (3)	0.060 (3)	0.048 (2)	0.013 (2)	−0.0016 (19)	0.0076 (19)
C6	0.048 (2)	0.059 (3)	0.057 (2)	0.0057 (19)	−0.0044 (18)	0.001 (2)
C7	0.042 (2)	0.038 (2)	0.060 (2)	0.0013 (17)	−0.0050 (17)	−0.0045 (18)
C8	0.049 (2)	0.044 (2)	0.050 (2)	−0.0030 (18)	−0.0013 (17)	0.0001 (18)
C9	0.044 (2)	0.042 (2)	0.051 (2)	−0.0036 (17)	−0.0047 (17)	−0.0007 (17)
C10	0.054 (2)	0.069 (3)	0.051 (2)	0.0032 (19)	0.0006 (18)	0.014 (2)
C11	0.054 (2)	0.094 (4)	0.059 (3)	0.001 (2)	0.008 (2)	0.016 (2)
C12	0.037 (2)	0.087 (3)	0.064 (3)	0.000 (2)	0.0038 (19)	0.012 (2)
C13	0.052 (2)	0.073 (3)	0.063 (3)	0.003 (2)	−0.009 (2)	0.015 (2)
C14	0.046 (2)	0.056 (2)	0.058 (2)	−0.0063 (18)	0.0020 (18)	0.0086 (19)

O1—N1	1.228 (7)	C2—H2A	0.9300
O2—N1	1.221 (7)	C3—C4	1.367 (5)
O1'—N1	1.228 (7)	C3—H3	0.9300
O2'—N1	1.222 (7)	C4—C5	1.372 (5)
O3—C7	1.214 (4)	C5—C6	1.374 (5)
O4—C8	1.209 (4)	C5—H5	0.9300
O5—N3	1.235 (7)	C6—H6	0.9300
O6—N3	1.237 (7)	C8—C9	1.496 (5)
O5'—N3	1.236 (7)	C9—C14	1.383 (5)
O6'—N3	1.254 (7)	C9—C10	1.385 (5)
N1—C4	1.475 (5)	C10—C11	1.363 (5)
N2—C7	1.380 (4)	C10—H10	0.9300
N2—C8	1.388 (4)	C11—C12	1.377 (6)
N2—H2	0.8800	C11—H11	0.9300
N3—C12	1.466 (5)	C12—C13	1.360 (6)
C1—C2	1.391 (5)	C13—C14	1.381 (5)
C1—C6	1.391 (5)	C13—H13	0.9300
C1—C7	1.488 (5)	C14—H14	0.9300
C2—C3	1.378 (5)
O2—N1—O1	123 (3)	C4—C5—H5	121.1
O2'—N1—O1'	126 (3)	C6—C5—H5	121.1
O2—N1—C4	118.4 (19)	C5—C6—C1	121.2 (4)
O2'—N1—C4	118.9 (19)	C5—C6—H6	119.4
O1—N1—C4	118 (2)	C1—C6—H6	119.4
O1'—N1—C4	115 (2)	O3—C7—N2	123.7 (3)
C7—N2—C8	125.2 (3)	O3—C7—C1	120.5 (3)
C7—N2—H2	117.4	N2—C7—C1	115.7 (3)
C8—N2—H2	117.4	O4—C8—N2	123.4 (3)
O5—N3—O6	122.7 (12)	O4—C8—C9	121.6 (3)
O5—N3—O6'	112.7 (10)	N2—C8—C9	115.0 (3)
O5'—N3—O6'	124.8 (12)	C14—C9—C10	119.5 (3)
O5—N3—C12	119.4 (8)	C14—C9—C8	121.2 (3)
O6—N3—C12	117.9 (9)	C10—C9—C8	119.0 (3)
O5'—N3—C12	118.2 (8)	C11—C10—C9	120.9 (4)
O6'—N3—C12	117.0 (9)	C11—C10—H10	119.5
C2—C1—C6	119.0 (3)	C9—C10—H10	119.5
C2—C1—C7	118.0 (3)	C10—C11—C12	118.2 (4)
C6—C1—C7	123.0 (3)	C10—C11—H11	120.9
C3—C2—C1	120.3 (3)	C12—C11—H11	120.9
C3—C2—H2A	119.9	C13—C12—C11	122.7 (4)
C1—C2—H2A	119.9	C13—C12—N3	117.5 (4)
C4—C3—C2	118.6 (4)	C11—C12—N3	119.8 (3)
C4—C3—H3	120.7	C12—C13—C14	118.6 (4)
C2—C3—H3	120.7	C12—C13—H13	120.7
C3—C4—C5	123.1 (3)	C14—C13—H13	120.7
C3—C4—N1	117.7 (4)	C13—C14—C9	120.0 (3)
C5—C4—N1	119.3 (3)	C13—C14—H14	120.0
C4—C5—C6	117.8 (3)	C9—C14—H14	120.0
C6—C1—C2—C3	0.4 (5)	C7—N2—C8—O4	14.3 (6)
C7—C1—C2—C3	177.8 (3)	C7—N2—C8—C9	−162.8 (3)
C1—C2—C3—C4	−1.3 (6)	O4—C8—C9—C14	−153.9 (4)
C2—C3—C4—C5	1.0 (6)	N2—C8—C9—C14	23.3 (5)
C2—C3—C4—N1	−179.0 (3)	O4—C8—C9—C10	20.4 (5)
O2—N1—C4—C3	8.3 (14)	N2—C8—C9—C10	−162.4 (3)
O2'—N1—C4—C3	−9.7 (14)	C14—C9—C10—C11	0.6 (6)
O1—N1—C4—C3	−171.8 (14)	C8—C9—C10—C11	−173.8 (4)
O1'—N1—C4—C3	170.3 (14)	C9—C10—C11—C12	0.5 (6)
O2—N1—C4—C5	−171.7 (14)	C10—C11—C12—C13	−1.5 (7)
O2'—N1—C4—C5	170.3 (14)	C10—C11—C12—N3	177.6 (4)
O1—N1—C4—C5	8.2 (14)	O5—N3—C12—C13	−160.6 (6)
O1'—N1—C4—C5	−9.7 (14)	O6—N3—C12—C13	19.3 (6)
C3—C4—C5—C6	0.3 (6)	O5'—N3—C12—C13	161.1 (6)
N1—C4—C5—C6	−179.7 (3)	O6'—N3—C12—C13	−18.9 (6)
C4—C5—C6—C1	−1.3 (6)	O5—N3—C12—C11	20.2 (6)
C2—C1—C6—C5	1.0 (6)	O6—N3—C12—C11	−159.9 (6)
C7—C1—C6—C5	−176.3 (3)	O5'—N3—C12—C11	−18.1 (6)
C8—N2—C7—O3	−4.9 (6)	O6'—N3—C12—C11	161.9 (6)
C8—N2—C7—C1	173.0 (3)	C11—C12—C13—C14	1.4 (7)
C2—C1—C7—O3	−38.2 (5)	N3—C12—C13—C14	−177.7 (4)
C6—C1—C7—O3	139.1 (4)	C12—C13—C14—C9	−0.3 (6)
C2—C1—C7—N2	143.8 (3)	C10—C9—C14—C13	−0.7 (6)
C6—C1—C7—N2	−38.9 (5)	C8—C9—C14—C13	173.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3i	0.88	2.08	2.951 (4)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O3i	0.88	2.08	2.951 (4)	170

Symmetry code: (i) .