1,2-Bis(2,4-di­nitro­phenoxy)­ethane

The title compound, C₁₄H₁₀N₄O₁₀, crystallizes in the monoclinic space group C2/c with the molecule on an inversion centre. The nitro groups are slightly twisted away from the planes of the benzene rings. In the crystal structure, weak intermolecular C—H...O interactions link the mol­ecules into layers which can be describedby an R₂²(10) ring and a C(6) chain.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.048
• wR factor = 0.148
• Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT142_ALERT_4_C su on b - Axis Small or Missing (x 100000) .....         10 Ang.
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for         N1
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for         N2
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.67

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997) and PLATON (Spek, 1990); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

1,2-Bis(2,4-dinitrophenoxy)ethane

Crystal data

C14H10N4O10	F(000) = 808
Mr = 394.26	Dx = 1.657 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2638 reflections
a = 6.8876 (1) Å	θ = 2.5–27.9°
b = 13.9289 (1) Å	µ = 0.14 mm^−1
c = 16.5396 (5) Å	T = 293 K
β = 95.146 (3)°	Block, yellow
V = 1580.36 (5) Å^3	0.26 × 0.20 × 0.12 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	1542 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.015
Graphite monochromator	θmax = 28.0°, θmin = 2.5°
ω scans	h = −6→9
4664 measured reflections	k = −15→17
1792 independent reflections	l = −21→21

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.148	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0894P)^2 + 0.878P] where P = (Fo^2 + 2Fc^2)/3
1792 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.38 e Å^−3
0 restraints	Δρmin = −0.25 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.3837 (2)	0.23623 (9)	−0.07525 (7)	0.0646 (4)
O2	0.4657 (3)	0.09374 (9)	−0.04384 (9)	0.0793 (5)
O3	0.7403 (3)	0.00324 (11)	0.21380 (11)	0.0934 (7)
O4	0.8188 (3)	0.10809 (13)	0.30593 (8)	0.0812 (6)
O5	0.51519 (19)	0.37389 (7)	0.01678 (7)	0.0442 (3)
N1	0.45934 (19)	0.17840 (9)	−0.02822 (7)	0.0384 (3)
N2	0.7527 (3)	0.08578 (12)	0.23784 (9)	0.0564 (4)
C1	0.5714 (2)	0.30735 (10)	0.07237 (8)	0.0358 (3)
C2	0.5481 (2)	0.20956 (9)	0.05134 (8)	0.0341 (3)
C3	0.6079 (2)	0.13769 (10)	0.10523 (9)	0.0384 (4)
H3	0.5927	0.0735	0.0906	0.046*
C4	0.6908 (2)	0.16298 (11)	0.18121 (9)	0.0418 (4)
C5	0.7149 (2)	0.25779 (12)	0.20481 (9)	0.0453 (4)
H5	0.7704	0.2731	0.2565	0.054*
C6	0.6556 (3)	0.32923 (11)	0.15056 (9)	0.0433 (4)
H6	0.6717	0.3931	0.1660	0.052*
C7	0.5376 (3)	0.47355 (10)	0.03792 (9)	0.0436 (4)
H7A	0.6734	0.4890	0.0529	0.052*
H7B	0.4621	0.4896	0.0828	0.052*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.1056 (11)	0.0380 (7)	0.0440 (7)	0.0066 (6)	−0.0280 (7)	0.0018 (5)
O2	0.1328 (14)	0.0302 (6)	0.0661 (9)	0.0062 (7)	−0.0400 (9)	−0.0109 (5)
O3	0.1582 (18)	0.0432 (8)	0.0706 (10)	0.0037 (9)	−0.0344 (11)	0.0186 (7)
O4	0.1260 (15)	0.0755 (10)	0.0376 (7)	0.0255 (9)	−0.0183 (8)	0.0078 (6)
O5	0.0703 (8)	0.0225 (5)	0.0375 (5)	0.0026 (4)	−0.0085 (5)	0.0005 (4)
N1	0.0494 (7)	0.0278 (6)	0.0362 (6)	0.0001 (5)	−0.0053 (5)	−0.0013 (4)
N2	0.0744 (10)	0.0516 (9)	0.0409 (8)	0.0102 (7)	−0.0066 (7)	0.0130 (6)
C1	0.0469 (8)	0.0255 (7)	0.0341 (7)	0.0023 (5)	−0.0012 (6)	0.0006 (5)
C2	0.0429 (7)	0.0263 (7)	0.0321 (6)	0.0009 (5)	−0.0020 (5)	−0.0002 (5)
C3	0.0483 (8)	0.0272 (7)	0.0386 (7)	0.0021 (5)	−0.0022 (6)	0.0030 (5)
C4	0.0518 (9)	0.0375 (8)	0.0350 (7)	0.0050 (6)	−0.0020 (6)	0.0072 (6)
C5	0.0573 (10)	0.0443 (9)	0.0327 (7)	0.0028 (7)	−0.0051 (6)	−0.0025 (6)
C6	0.0598 (9)	0.0318 (7)	0.0367 (7)	0.0001 (6)	−0.0040 (7)	−0.0049 (6)
C7	0.0647 (10)	0.0229 (7)	0.0413 (8)	0.0026 (6)	−0.0052 (7)	−0.0019 (5)

Geometric parameters (Å, º)

O1—N1	1.205 (2)	C2—C3	1.379 (2)
O2—N1	1.209 (2)	C3—C4	1.379 (2)
O3—N2	1.217 (2)	C3—H3	0.93
O4—N2	1.217 (2)	C4—C5	1.383 (2)
O5—C1	1.338 (2)	C5—C6	1.377 (2)
O5—C7	1.437 (2)	C5—H5	0.93
N1—C2	1.466 (2)	C6—H6	0.93
N2—C4	1.464 (2)	C7—C7^i	1.506 (3)
C1—C6	1.403 (2)	C7—H7A	0.97
C1—C2	1.411 (2)	C7—H7B	0.97
C1—O5—C7	118.9 (1)	C3—C4—C5	122.1 (1)
O1—N1—O2	122.4 (1)	C3—C4—N2	117.9 (1)
O1—N1—C2	120.2 (1)	C5—C4—N2	120.0 (1)
O2—N1—C2	117.4 (1)	C6—C5—C4	119.0 (1)
O3—N2—O4	123.6 (2)	C6—C5—H5	120.5
O3—N2—C4	118.5 (2)	C4—C5—H5	120.5
O4—N2—C4	117.9 (2)	C5—C6—C1	121.2 (1)
O5—C1—C6	123.6 (1)	C5—C6—H6	119.4
O5—C1—C2	118.7 (1)	C1—C6—H6	119.4
C6—C1—C2	117.7 (1)	O5—C7—C7^i	104.4 (2)
C3—C2—C1	121.4 (1)	O5—C7—H7A	110.9
C3—C2—N1	116.2 (1)	C7^i—C7—H7A	110.9
C1—C2—N1	122.4 (1)	O5—C7—H7B	110.9
C2—C3—C4	118.6 (1)	C7^i—C7—H7B	110.9
C2—C3—H3	120.7	H7A—C7—H7B	108.9
C4—C3—H3	120.7
C7—O5—C1—C6	−1.4 (2)	C2—C3—C4—C5	0.2 (2)
C7—O5—C1—C2	179.71 (14)	C2—C3—C4—N2	179.73 (14)
O5—C1—C2—C3	178.27 (13)	O3—N2—C4—C3	4.8 (3)
C6—C1—C2—C3	−0.7 (2)	O4—N2—C4—C3	−177.17 (18)
O5—C1—C2—N1	−1.9 (2)	O3—N2—C4—C5	−175.72 (19)
C6—C1—C2—N1	179.09 (13)	O4—N2—C4—C5	2.4 (3)
O1—N1—C2—C3	171.65 (15)	C3—C4—C5—C6	−0.5 (3)
O2—N1—C2—C3	−8.3 (2)	N2—C4—C5—C6	−179.99 (15)
O1—N1—C2—C1	−8.2 (2)	C4—C5—C6—C1	0.1 (3)
O2—N1—C2—C1	171.86 (17)	O5—C1—C6—C5	−178.49 (15)
C1—C2—C3—C4	0.4 (2)	C2—C1—C6—C5	0.4 (2)
N1—C2—C3—C4	−179.42 (14)	C1—O5—C7—C7^i	179.55 (16)

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2^ii	0.93	2.48	3.404 (2)	176
C6—H6···O3^iii	0.93	2.54	3.337 (2)	144

Symmetry codes: (ii) −x+1, −y, −z; (iii) −x+3/2, y+1/2, −z+1/2.