1,4-Bis(2-nitro-phen-oxy)butane.

The asymmetric unit of the title compound, C(16)H(16)N(2)O(6), contains one-half mol-ecule, the mid-point of the central C-C bond being located on a crystallographic inversion center. The crystal structure shows weak inter-actions between the O atoms of the nitro groups and two different C-H groups of the benzene rings. The extended weak hydrogen-bond formation, involving the NO(2) groups, generates an infinite three-dimensional network.

Related literature

For related structures, see: Han & Zhen (2005 ▶); Naz et al. (2007 ▶); Zhang et al. (2007 ▶). For recent examples of complexes with macrocyclic ligands, including diether subunits, see: Fernández et al. (2008 ▶); Platas-Iglesias et al. (2005 ▶); Tas et al. (2006 ▶).

Experimental

Crystal data

C16H16N2O6

M = 332.31

Monoclinic,

a = 7.7977 (8) Å

b = 13.888 (2) Å

c = 7.6729 (8) Å

β = 110.866 (6)°

V = 776.4 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.7 × 0.6 × 0.4 mm

Data collection

Bruker P4 diffractometer

Absorption correction: none

3850 measured reflections

2256 independent reflections

1752 reflections with I > 2σ(I)

R int = 0.030

3 standard reflections every 97 reflections intensity decay: 2.3%

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.130

S = 1.06

2256 reflections

110 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.19 e Å−3

Data collection: XSCANS (Siemens, 1996 ▶); cell refinement: XSCANS; data reduction: SHELXTL-Plus (Sheldrick, 2008 ▶); program(s) used to solve structure: SHELXTL-Plus; program(s) used to refine structure: SHELXTL-Plus; molecular graphics: SHELXTL-Plus and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXTL-Plus.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809048909/im2156sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809048909/im2156Isup2.hkl

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

C16H16N2O6	F(000) = 348
Mr = 332.31	Dx = 1.421 Mg m−3
Monoclinic, P21/c	Melting point = 442–443 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.7977 (8) Å	Cell parameters from 85 reflections
b = 13.888 (2) Å	θ = 5.2–12.4°
c = 7.6729 (8) Å	µ = 0.11 mm−1
β = 110.866 (6)°	T = 296 K
V = 776.4 (2) Å3	Block, colorless
Z = 2	0.7 × 0.6 × 0.4 mm

Bruker P4 diffractometer	Rint = 0.030
Radiation source: fine-focus sealed tube	θmax = 30.0°, θmin = 2.9°
graphite	h = −10→10
ω scan	k = −1→19
3850 measured reflections	l = −10→5
2256 independent reflections	3 standard reflections every 97 reflections
1752 reflections with I > 2σ(I)	intensity decay: 2.3%

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0452P)2 + 0.1839P] where P = (Fo2 + 2Fc2)/3
2256 reflections	(Δ/σ)max < 0.001
110 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

Experimental. Experimental absorption correction were not applied because the molecule is purely organic, and no better structure refinement was obtained.

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
O1	0.19481 (19)	0.21566 (10)	0.9250 (3)	0.0923 (5)
O2	0.32880 (19)	0.33983 (9)	0.8740 (2)	0.0827 (4)
O3	0.28310 (12)	0.07009 (6)	0.74649 (13)	0.0474 (3)
N1	0.32195 (16)	0.25370 (9)	0.89929 (17)	0.0506 (3)
C1	0.47947 (16)	0.19562 (9)	0.90340 (16)	0.0392 (3)
C2	0.65074 (18)	0.23662 (10)	0.98583 (19)	0.0487 (3)
H2A	0.6618	0.2979	1.0376	0.058*
C3	0.80442 (19)	0.18694 (12)	0.9912 (2)	0.0575 (4)
H3A	0.9205	0.2136	1.0478	0.069*
C4	0.7837 (2)	0.09688 (12)	0.9114 (2)	0.0579 (4)
H4A	0.8874	0.0634	0.9126	0.070*
C5	0.61331 (19)	0.05505 (10)	0.8296 (2)	0.0497 (3)
H5A	0.6038	−0.0060	0.7772	0.060*
C6	0.45534 (16)	0.10362 (9)	0.82495 (16)	0.0388 (3)
C7	0.2563 (2)	−0.01938 (9)	0.6464 (2)	0.0495 (3)
H7A	0.3192	−0.0712	0.7294	0.059*
H7B	0.3044	−0.0151	0.5462	0.059*
C8	0.0531 (2)	−0.03792 (10)	0.5688 (2)	0.0534 (4)
H8A	0.0081	−0.0418	0.6699	0.064*
H8B	0.0315	−0.0991	0.5063	0.064*

	U11	U22	U33	U12	U13	U23
O1	0.0717 (8)	0.0766 (9)	0.1558 (14)	−0.0089 (7)	0.0739 (9)	−0.0235 (9)
O2	0.0880 (9)	0.0461 (6)	0.1202 (12)	0.0135 (6)	0.0448 (8)	0.0006 (7)
O3	0.0423 (5)	0.0429 (5)	0.0527 (5)	−0.0051 (4)	0.0117 (4)	−0.0121 (4)
N1	0.0481 (6)	0.0500 (6)	0.0554 (7)	−0.0005 (5)	0.0205 (5)	−0.0119 (5)
C1	0.0392 (6)	0.0400 (6)	0.0386 (6)	−0.0007 (4)	0.0142 (5)	−0.0014 (5)
C2	0.0467 (7)	0.0481 (7)	0.0479 (7)	−0.0098 (5)	0.0125 (5)	−0.0025 (5)
C3	0.0388 (6)	0.0690 (9)	0.0584 (8)	−0.0073 (6)	0.0098 (6)	0.0055 (7)
C4	0.0425 (7)	0.0699 (9)	0.0606 (9)	0.0146 (6)	0.0174 (6)	0.0126 (7)
C5	0.0506 (7)	0.0459 (7)	0.0510 (7)	0.0100 (5)	0.0160 (6)	0.0012 (6)
C6	0.0393 (6)	0.0388 (6)	0.0365 (5)	−0.0013 (4)	0.0111 (4)	0.0003 (4)
C7	0.0574 (8)	0.0354 (6)	0.0501 (7)	−0.0045 (5)	0.0122 (6)	−0.0054 (5)
C8	0.0603 (8)	0.0385 (6)	0.0520 (8)	−0.0123 (6)	0.0085 (6)	0.0006 (5)

O1—N1	1.2000 (16)	C4—C5	1.380 (2)
O2—N1	1.2159 (17)	C4—H4A	0.9300
O3—C6	1.3443 (15)	C5—C6	1.3937 (18)
O3—C7	1.4363 (15)	C5—H5A	0.9300
N1—C1	1.4604 (16)	C7—C8	1.504 (2)
C1—C2	1.3807 (17)	C7—H7A	0.9700
C1—C6	1.3962 (17)	C7—H7B	0.9700
C2—C3	1.371 (2)	C8—C8i	1.512 (3)
C2—H2A	0.9300	C8—H8A	0.9600
C3—C4	1.377 (2)	C8—H8B	0.9601
C3—H3A	0.9300
C6—O3—C7	118.09 (10)	C4—C5—H5A	119.8
O1—N1—O2	123.04 (14)	C6—C5—H5A	119.8
O1—N1—C1	119.40 (13)	O3—C6—C5	125.22 (12)
O2—N1—C1	117.54 (12)	O3—C6—C1	118.02 (11)
C2—C1—C6	122.32 (11)	C5—C6—C1	116.73 (11)
C2—C1—N1	116.81 (11)	O3—C7—C8	106.96 (11)
C6—C1—N1	120.86 (11)	O3—C7—H7A	110.3
C3—C2—C1	119.93 (13)	C8—C7—H7A	110.3
C3—C2—H2A	120.0	O3—C7—H7B	110.3
C1—C2—H2A	120.0	C8—C7—H7B	110.3
C2—C3—C4	118.77 (13)	H7A—C7—H7B	108.6
C2—C3—H3A	120.6	C7—C8—C8i	113.25 (14)
C4—C3—H3A	120.6	C7—C8—H8A	109.1
C3—C4—C5	121.74 (13)	C8i—C8—H8A	109.7
C3—C4—H4A	119.1	C7—C8—H8B	108.7
C5—C4—H4A	119.1	C8i—C8—H8B	108.2
C4—C5—C6	120.48 (13)	H8A—C8—H8B	107.7
O1—N1—C1—C2	−141.19 (16)	C7—O3—C6—C1	172.71 (11)
O2—N1—C1—C2	37.07 (18)	C4—C5—C6—O3	178.93 (13)
O1—N1—C1—C6	39.59 (19)	C4—C5—C6—C1	1.0 (2)
O2—N1—C1—C6	−142.15 (14)	C2—C1—C6—O3	−179.48 (12)
C6—C1—C2—C3	0.5 (2)	N1—C1—C6—O3	−0.30 (17)
N1—C1—C2—C3	−178.69 (13)	C2—C1—C6—C5	−1.43 (18)
C1—C2—C3—C4	0.8 (2)	N1—C1—C6—C5	177.75 (12)
C2—C3—C4—C5	−1.2 (2)	C6—O3—C7—C8	−178.18 (11)
C3—C4—C5—C6	0.2 (2)	O3—C7—C8—C8i	62.6 (2)
C7—O3—C6—C5	−5.15 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O1ii	0.93	2.63	3.284 (2)	128
C5—H5A···O2iii	0.93	2.58	3.476 (2)	163
C8—H8B···O3i	0.96	2.56	2.900 (2)	101

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯O1i	0.93	2.63	3.284 (2)	128
C5—H5A⋯O2ii	0.93	2.58	3.476 (2)	163

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