1-Nitro-4-(4-nitro-phen-oxy)benzene: a second monoclinic polymorph.

In the title compound, C12H8N2O5, the aromatic rings are inclined to one another by 56.14 (7)°. The nitro groups are inclined by to the benzene rings to which they are attached by 3.86 (17) and 9.65 (15)°. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, forming a three-dimensional structure. The title compound is a new monoclinic polymorph, crystallizing in space group P21/c. The first polymorph crystallized in space group C2/c and the mol-ecule possesses twofold rotation symmetry. Two low-temperature structures of this polymorph (150 K and 100 K, respectively) have been reported [Meciarova et al. (2004). Private Communication (refcode IXOGAD). CCDC, Cambridge, England, and Dey & Desiraju (2005). Chem. Commun. pp. 2486-2488].

Related literature

For the crystal structure of the monoclinic C2/c polymorph of the title compound, see: Meciarova et al. (2004 ▶); Dey & Desiraju (2005 ▶).

Experimental

Crystal data

C12H8N2O5

M = 260.20

Monoclinic,

a = 8.1114 (5) Å

b = 11.8942 (7) Å

c = 12.3970 (7) Å

β = 106.402 (1)°

V = 1147.37 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 150 K

0.36 × 0.35 × 0.25 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2012 ▶) T min = 0.794, T max = 0.862

10808 measured reflections

2641 independent reflections

2149 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.104

S = 1.06

2641 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker 1998 ▶); cell refinement: SAINT (Bruker 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813029346/ds2235sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813029346/ds2235Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813029346/ds2235Isup3.cml

968365

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

C12H8N2O5	F(000) = 536
Mr = 260.20	Dx = 1.506 Mg m−3
Monoclinic, P21/c	Melting point: 416 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.1114 (5) Å	Cell parameters from 3529 reflections
b = 11.8942 (7) Å	θ = 2.4–30.6°
c = 12.3970 (7) Å	µ = 0.12 mm−1
β = 106.402 (1)°	T = 150 K
V = 1147.37 (12) Å3	Block, yellow
Z = 4	0.36 × 0.35 × 0.25 mm

Bruker APEXII CCD diffractometer	2149 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
ω rotation with narrow frames scans	θmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2012)	h = −10→10
Tmin = 0.794, Tmax = 0.862	k = −15→15
10808 measured reflections	l = −16→16
2641 independent reflections

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039	H-atom parameters constrained
wR(F2) = 0.104	w = 1/[σ2(Fo2) + (0.0456P)2 + 0.2844P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
2641 reflections	Δρmax = 0.23 e Å−3
172 parameters	Δρmin = −0.26 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.

	x	y	z	Uiso*/Ueq
O1	0.44094 (13)	0.19652 (8)	0.09931 (8)	0.0438 (3)
C11	0.32514 (17)	0.12641 (11)	0.02667 (11)	0.0346 (3)
C12	0.3348 (2)	0.01415 (11)	0.05873 (12)	0.0427 (3)
H12	0.4100	−0.0082	0.1290	0.051*
C13	0.2350 (2)	−0.06452 (11)	−0.01166 (12)	0.0414 (3)
H13	0.2406	−0.1416	0.0092	0.050*
C14	0.12673 (16)	−0.02940 (10)	−0.11323 (11)	0.0341 (3)
N11	0.02465 (15)	−0.11328 (10)	−0.18957 (11)	0.0427 (3)
O11	−0.07448 (13)	−0.08066 (10)	−0.27901 (11)	0.0564 (3)
O12	0.04440 (16)	−0.21295 (9)	−0.16171 (11)	0.0581 (3)
C15	0.11403 (17)	0.08250 (11)	−0.14550 (12)	0.0361 (3)
H15	0.0368	0.1048	−0.2151	0.043*
C16	0.21520 (17)	0.16134 (10)	−0.07512 (11)	0.0349 (3)
H16	0.2095	0.2384	−0.0961	0.042*
C21	0.41096 (18)	0.31038 (11)	0.10392 (11)	0.0353 (3)
C22	0.55556 (17)	0.37841 (12)	0.12879 (11)	0.0369 (3)
H22	0.6661	0.3464	0.1384	0.044*
C23	0.53798 (17)	0.49294 (11)	0.13949 (10)	0.0359 (3)
H23	0.6357	0.5408	0.1552	0.043*
C24	0.37637 (17)	0.53685 (11)	0.12704 (10)	0.0329 (3)
N21	0.35664 (16)	0.65877 (9)	0.13676 (9)	0.0388 (3)
O21	0.21649 (15)	0.69525 (9)	0.13919 (11)	0.0592 (3)
O22	0.48044 (14)	0.71924 (8)	0.14138 (9)	0.0477 (3)
C25	0.23130 (18)	0.46974 (12)	0.10442 (12)	0.0394 (3)
H25	0.1215	0.5018	0.0975	0.047*
C26	0.24867 (18)	0.35511 (12)	0.09212 (13)	0.0420 (3)
H26	0.1507	0.3075	0.0758	0.050*

	U11	U22	U33	U12	U13	U23
O1	0.0519 (6)	0.0328 (5)	0.0393 (5)	0.0013 (4)	0.0010 (4)	−0.0048 (4)
C11	0.0417 (7)	0.0300 (6)	0.0332 (6)	−0.0018 (5)	0.0122 (5)	−0.0024 (5)
C12	0.0603 (9)	0.0338 (7)	0.0329 (7)	0.0052 (6)	0.0115 (6)	0.0050 (5)
C13	0.0597 (9)	0.0258 (6)	0.0430 (8)	0.0006 (6)	0.0217 (7)	0.0047 (5)
C14	0.0336 (6)	0.0294 (6)	0.0435 (7)	−0.0040 (5)	0.0176 (6)	−0.0047 (5)
N11	0.0383 (6)	0.0374 (6)	0.0580 (8)	−0.0086 (5)	0.0227 (6)	−0.0107 (6)
O11	0.0338 (5)	0.0551 (7)	0.0719 (8)	−0.0026 (5)	0.0012 (5)	−0.0181 (6)
O12	0.0775 (8)	0.0332 (6)	0.0725 (8)	−0.0187 (5)	0.0357 (7)	−0.0101 (5)
C15	0.0343 (7)	0.0336 (7)	0.0393 (7)	0.0009 (5)	0.0084 (5)	0.0012 (5)
C16	0.0406 (7)	0.0254 (6)	0.0381 (7)	−0.0007 (5)	0.0102 (5)	0.0035 (5)
C21	0.0466 (7)	0.0309 (6)	0.0280 (6)	−0.0022 (5)	0.0098 (5)	−0.0016 (5)
C22	0.0358 (7)	0.0425 (7)	0.0290 (6)	0.0004 (6)	0.0035 (5)	−0.0008 (5)
C23	0.0371 (7)	0.0388 (7)	0.0294 (6)	−0.0090 (5)	0.0055 (5)	−0.0011 (5)
C24	0.0433 (7)	0.0308 (6)	0.0253 (6)	−0.0057 (5)	0.0106 (5)	0.0002 (5)
N21	0.0512 (7)	0.0340 (6)	0.0327 (6)	−0.0057 (5)	0.0142 (5)	0.0016 (5)
O21	0.0606 (7)	0.0381 (6)	0.0882 (9)	0.0030 (5)	0.0362 (7)	0.0020 (6)
O22	0.0576 (6)	0.0370 (5)	0.0488 (6)	−0.0158 (5)	0.0153 (5)	−0.0031 (4)
C25	0.0384 (7)	0.0375 (7)	0.0458 (8)	−0.0033 (6)	0.0174 (6)	−0.0044 (6)
C26	0.0420 (7)	0.0370 (7)	0.0511 (8)	−0.0107 (6)	0.0196 (6)	−0.0085 (6)

O1—C21	1.3799 (16)	C16—H16	0.9500
O1—C11	1.3824 (16)	C21—C22	1.3861 (19)
C11—C16	1.3873 (18)	C21—C26	1.389 (2)
C11—C12	1.3890 (19)	C22—C23	1.3801 (19)
C12—C13	1.376 (2)	C22—H22	0.9500
C12—H12	0.9500	C23—C24	1.3787 (19)
C13—C14	1.381 (2)	C23—H23	0.9500
C13—H13	0.9500	C24—C25	1.3835 (18)
C14—C15	1.3852 (18)	C24—N21	1.4677 (17)
C14—N11	1.4608 (17)	N21—O22	1.2233 (15)
N11—O12	1.2325 (16)	N21—O21	1.2251 (16)
N11—O11	1.2340 (17)	C25—C26	1.384 (2)
C15—C16	1.3819 (18)	C25—H25	0.9500
C15—H15	0.9500	C26—H26	0.9500
C21—O1—C11	121.58 (10)	O1—C21—C22	115.73 (12)
O1—C11—C16	123.77 (12)	O1—C21—C26	122.99 (12)
O1—C11—C12	114.87 (12)	C22—C21—C26	121.14 (12)
C16—C11—C12	121.19 (12)	C23—C22—C21	119.58 (13)
C13—C12—C11	119.79 (13)	C23—C22—H22	120.2
C13—C12—H12	120.1	C21—C22—H22	120.2
C11—C12—H12	120.1	C24—C23—C22	118.95 (12)
C12—C13—C14	118.77 (12)	C24—C23—H23	120.5
C12—C13—H13	120.6	C22—C23—H23	120.5
C14—C13—H13	120.6	C23—C24—C25	122.11 (12)
C13—C14—C15	122.02 (12)	C23—C24—N21	119.17 (11)
C13—C14—N11	118.84 (12)	C25—C24—N21	118.72 (12)
C15—C14—N11	119.13 (12)	O22—N21—O21	123.08 (12)
O12—N11—O11	123.66 (13)	O22—N21—C24	118.53 (12)
O12—N11—C14	118.06 (13)	O21—N21—C24	118.38 (11)
O11—N11—C14	118.27 (12)	C24—C25—C26	118.92 (13)
C16—C15—C14	119.16 (12)	C24—C25—H25	120.5
C16—C15—H15	120.4	C26—C25—H25	120.5
C14—C15—H15	120.4	C25—C26—C21	119.27 (12)
C15—C16—C11	119.06 (12)	C25—C26—H26	120.4
C15—C16—H16	120.5	C21—C26—H26	120.4
C11—C16—H16	120.5

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O21i	0.95	2.56	3.4413 (18)	153
C23—H23···O11ii	0.95	2.31	3.1933 (18)	154
C26—H26···O12iii	0.95	2.42	3.227 (2)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O21i	0.95	2.56	3.4413 (18)	153
C23—H23⋯O11ii	0.95	2.31	3.1933 (18)	154
C26—H26⋯O12iii	0.95	2.42	3.227 (2)	143

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