1,2-Bis(p-nitro­phen­oxy)ethane

Mol­ecules of the title compound, C₁₄H₁₂N₂O₆, are located on centres of inversion. The mol­ecule is essentially planar, with the exception of the nitro group, which is twisted slightly out of the plane of the remaining atoms.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.036
• wR factor = 0.102
• Data-to-parameter ratio = 14.6

checkCIF/PLATON results

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Computing details

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97.

1,2-Bis(p-nitrophenoxy)ethylene

Crystal data

C14H12N2O6	F(000) = 316
Mr = 304.26	Dx = 1.471 Mg m^−3
Monoclinic, P21/n	Melting point: 432 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 9.1465 (12) Å	Cell parameters from 8996 reflections
b = 7.3137 (7) Å	θ = 3.6–27.2°
c = 10.2852 (13) Å	µ = 0.12 mm^−1
β = 93.353 (10)°	T = 173 K
V = 686.85 (14) Å^3	Block, light yellow
Z = 2	0.49 × 0.46 × 0.44 mm

Data collection

Stoe IPDS-II two-circle diffractometer	1380 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.037
Graphite monochromator	θmax = 27.0°, θmin = 4.0°
ω scans	h = −11→11
8567 measured reflections	k = −9→8
1477 independent reflections	l = −13→13

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.036	H-atom parameters constrained
wR(F^2) = 0.103	w = 1/[σ^2(Fo^2) + (0.0586P)^2 + 0.1845P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
1477 reflections	Δρmax = 0.37 e Å^−3
101 parameters	Δρmin = −0.20 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.11 (2)

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
N1	0.32402 (10)	0.57146 (14)	0.80918 (9)	0.0217 (3)
O1	0.82156 (8)	0.59629 (11)	0.51718 (7)	0.0210 (2)
O2	0.21184 (9)	0.64765 (14)	0.76280 (9)	0.0322 (3)
O3	0.32999 (9)	0.48898 (12)	0.91408 (8)	0.0286 (3)
C1	0.70374 (11)	0.58452 (14)	0.59315 (10)	0.0174 (3)
C2	0.58574 (11)	0.70123 (14)	0.55763 (10)	0.0190 (3)
H2	0.5916	0.7824	0.4860	0.023*
C3	0.46058 (11)	0.69710 (15)	0.62798 (10)	0.0197 (3)
H3	0.3792	0.7732	0.6041	0.024*
C4	0.45655 (11)	0.57869 (15)	0.73473 (10)	0.0192 (3)
C5	0.57319 (12)	0.46538 (16)	0.77235 (11)	0.0227 (3)
H5	0.5683	0.3879	0.8461	0.027*
C6	0.69805 (11)	0.46696 (16)	0.70017 (11)	0.0223 (3)
H6	0.7784	0.3889	0.7235	0.027*
C7	0.94301 (11)	0.47511 (15)	0.54757 (11)	0.0211 (3)
H7A	0.9125	0.3459	0.5363	0.025*
H7B	0.9821	0.4933	0.6385	0.025*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0185 (5)	0.0250 (5)	0.0222 (5)	−0.0030 (3)	0.0047 (3)	−0.0054 (4)
O1	0.0141 (4)	0.0242 (4)	0.0255 (4)	0.0051 (3)	0.0061 (3)	0.0052 (3)
O2	0.0172 (4)	0.0468 (6)	0.0330 (5)	0.0046 (4)	0.0054 (3)	−0.0015 (4)
O3	0.0288 (5)	0.0335 (5)	0.0243 (4)	−0.0050 (3)	0.0093 (3)	0.0001 (3)
C1	0.0135 (5)	0.0191 (5)	0.0197 (5)	−0.0008 (4)	0.0022 (4)	−0.0024 (4)
C2	0.0178 (5)	0.0194 (5)	0.0198 (5)	0.0015 (4)	0.0017 (4)	0.0011 (4)
C3	0.0152 (5)	0.0214 (5)	0.0224 (5)	0.0030 (4)	0.0005 (4)	−0.0022 (4)
C4	0.0153 (5)	0.0230 (5)	0.0198 (5)	−0.0028 (4)	0.0043 (4)	−0.0043 (4)
C5	0.0216 (5)	0.0258 (6)	0.0211 (5)	0.0000 (4)	0.0034 (4)	0.0037 (4)
C6	0.0174 (5)	0.0248 (6)	0.0246 (6)	0.0043 (4)	0.0018 (4)	0.0043 (4)
C7	0.0142 (5)	0.0226 (5)	0.0269 (6)	0.0042 (4)	0.0044 (4)	0.0036 (4)

Geometric parameters (Å, º)

N1—O3	1.2346 (13)	C3—C4	1.4006 (15)
N1—O2	1.2384 (13)	C3—H3	0.9500
N1—C4	1.4721 (13)	C4—C5	1.3879 (16)
O1—C1	1.3703 (12)	C5—C6	1.3981 (14)
O1—C7	1.4411 (12)	C5—H5	0.9500
C1—C6	1.4000 (15)	C6—H6	0.9500
C1—C2	1.4074 (14)	C7—C7^i	1.515 (2)
C2—C3	1.3899 (14)	C7—H7A	0.9900
C2—H2	0.9500	C7—H7B	0.9900
O3—N1—O2	123.35 (9)	C5—C4—N1	118.46 (10)
O3—N1—C4	118.45 (9)	C3—C4—N1	119.36 (9)
O2—N1—C4	118.19 (9)	C4—C5—C6	119.05 (10)
C1—O1—C7	117.36 (8)	C4—C5—H5	120.5
O1—C1—C6	123.61 (9)	C6—C5—H5	120.5
O1—C1—C2	115.50 (9)	C5—C6—C1	119.44 (10)
C6—C1—C2	120.89 (9)	C5—C6—H6	120.3
C3—C2—C1	119.61 (10)	C1—C6—H6	120.3
C3—C2—H2	120.2	O1—C7—C7^i	105.24 (11)
C1—C2—H2	120.2	O1—C7—H7A	110.7
C2—C3—C4	118.80 (9)	C7^i—C7—H7A	110.7
C2—C3—H3	120.6	O1—C7—H7B	110.7
C4—C3—H3	120.6	C7^i—C7—H7B	110.7
C5—C4—C3	122.19 (10)	H7A—C7—H7B	108.8
C7—O1—C1—C6	2.41 (15)	O3—N1—C4—C3	−168.86 (10)
C7—O1—C1—C2	−178.10 (9)	O2—N1—C4—C3	11.59 (15)
O1—C1—C2—C3	179.13 (9)	C3—C4—C5—C6	−1.09 (17)
C6—C1—C2—C3	−1.36 (16)	N1—C4—C5—C6	178.14 (9)
C1—C2—C3—C4	1.31 (15)	C4—C5—C6—C1	1.03 (17)
C2—C3—C4—C5	−0.10 (16)	O1—C1—C6—C5	179.64 (10)
C2—C3—C4—N1	−179.31 (9)	C2—C1—C6—C5	0.17 (17)
O3—N1—C4—C5	11.90 (15)	C1—O1—C7—C7^i	−177.67 (10)
O2—N1—C4—C5	−167.66 (10)

Symmetry code: (i) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3^ii	0.95	2.48	3.4166 (14)	169

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