(2E)-3-[(1E)-2-(5-Nitro­isoxazol-3-yl)­vinyl­oxy]­prop-2-enal

The title compound, (2E)-3-[(1E)-2-(5-nitro­isoxazol-3-yl)­vinyl­oxy]­prop-2-enal, C₈H₆N₂O₅, was an unexpected product of the direct reaction of furan and nitro­acetyl­ene. It crystallizes in the monoclinic space group P2₁/c, and is an unsaturated compound with a density of 1.507 g cm⁻³. As a result of cooperative C—H...O hydrogen bonding, the title compound forms centrosymmetric planar dimers, which pack in stacks of almost-planar parallel layers.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.036
• wR factor = 0.101
• Data-to-parameter ratio = 9.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level B:



THETM_01  Alert B The value of sine(theta_max)/wavelength is less than 0.575
          Calculated sin(theta_max)/wavelength =    0.5555


 Alert Level C:



REFNR_01  Alert C Ratio of reflections to parameters is < 10 for a
          centrosymmetric structure
          sine(theta)/lambda                0.5555
          Proportion of unique data used    1.0000
          Ratio reflections to parameters   9.6569


 0 Alert Level A = Potentially serious problem

 1 Alert Level B = Potential problem

 1 Alert Level C = Please check

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SHELXTL (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(2E)-3-[(1E)-2-(5-nitroisoxazol-3-yl)vinyloxy]prop-2-enal

Crystal data

C8H6N2O5	Dx = 1.507 Mg m^−3
Mr = 210.15	Melting point: 174 K
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
a = 3.9575 (2) Å	Cell parameters from 2436 reflections
b = 12.3228 (4) Å	θ = 4.3–57.3°
c = 19.0970 (7) Å	µ = 1.12 mm^−1
β = 95.849 (2)°	T = 294 K
V = 926.46 (7) Å^3	Lath, colorless
Z = 4	0.16 × 0.12 × 0.02 mm
F(000) = 432

Data collection

CCD area-detector diffractometer	1323 independent reflections
Radiation source: fine-focus sealed tube	978 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
φ and ω scans	θmax = 58.9°, θmin = 4.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −4→4
Tmin = 0.86, Tmax = 0.98	k = −13→13
6207 measured reflections	l = −20→21

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.036	H-atom parameters constrained
wR(F^2) = 0.101	w = 1/[σ^2(Fo^2) + (0.0354P)^2 + 0.1275P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
1323 reflections	Δρmax = 0.12 e Å^−3
137 parameters	Δρmin = −0.14 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0083 (10)

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	0.1347 (4)	1.43897 (12)	0.29740 (8)	0.0893 (5)
N2	0.0773 (5)	1.33217 (16)	0.27220 (9)	0.0863 (6)
C3	0.2661 (5)	1.26860 (17)	0.31559 (10)	0.0704 (6)
C4	0.4493 (5)	1.32960 (18)	0.36973 (11)	0.0755 (6)
H4	0.5986	1.3046	0.4070	0.091*
C5	0.3571 (5)	1.43063 (19)	0.35451 (11)	0.0758 (6)
N5	0.4607 (6)	1.53217 (17)	0.38703 (12)	0.0945 (6)
O5A	0.6820 (6)	1.52726 (15)	0.43627 (11)	0.1206 (7)
O5B	0.3261 (6)	1.61513 (15)	0.36349 (12)	0.1248 (8)
C6	0.2598 (6)	1.15362 (18)	0.30201 (11)	0.0760 (6)
H6	0.1279	1.1285	0.2622	0.091*
C7	0.4293 (5)	1.08273 (17)	0.34258 (11)	0.0736 (6)
H7	0.5643	1.1052	0.3827	0.088*
O8	0.4060 (4)	0.97537 (12)	0.32542 (7)	0.0850 (5)
C9	0.5520 (6)	0.89912 (18)	0.36922 (11)	0.0785 (6)
H9	0.5193	0.8278	0.3541	0.094*
C10	0.7330 (5)	0.91113 (17)	0.42998 (10)	0.0736 (6)
H10	0.7760	0.9802	0.4484	0.088*
C11	0.8649 (6)	0.81747 (18)	0.46799 (11)	0.0797 (6)
H11	0.8143	0.7499	0.4479	0.096*
O12	1.0369 (5)	0.81927 (12)	0.52413 (8)	0.0969 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.1002 (12)	0.0723 (10)	0.0899 (10)	0.0062 (8)	−0.0174 (9)	0.0108 (8)
N2	0.0974 (14)	0.0722 (12)	0.0843 (12)	0.0041 (10)	−0.0158 (10)	0.0044 (10)
C3	0.0698 (13)	0.0700 (14)	0.0691 (12)	0.0011 (10)	−0.0045 (10)	0.0084 (10)
C4	0.0781 (14)	0.0726 (15)	0.0726 (12)	−0.0011 (11)	−0.0084 (10)	0.0075 (11)
C5	0.0782 (15)	0.0691 (15)	0.0779 (13)	−0.0029 (11)	−0.0030 (11)	0.0058 (11)
N5	0.1070 (17)	0.0707 (14)	0.1025 (15)	−0.0075 (11)	−0.0056 (12)	0.0028 (11)
O5A	0.1357 (17)	0.0958 (14)	0.1210 (14)	−0.0151 (11)	−0.0320 (13)	−0.0088 (10)
O5B	0.1492 (18)	0.0675 (12)	0.1507 (17)	0.0026 (11)	−0.0183 (13)	0.0051 (11)
C6	0.0777 (14)	0.0731 (15)	0.0733 (12)	−0.0010 (11)	−0.0110 (10)	0.0012 (11)
C7	0.0801 (14)	0.0627 (14)	0.0751 (12)	−0.0058 (10)	−0.0066 (11)	−0.0047 (10)
O8	0.1018 (12)	0.0668 (10)	0.0799 (9)	−0.0001 (8)	−0.0226 (8)	−0.0023 (7)
C9	0.0909 (16)	0.0604 (13)	0.0803 (13)	−0.0016 (11)	−0.0109 (12)	−0.0026 (11)
C10	0.0812 (15)	0.0620 (13)	0.0740 (12)	−0.0047 (10)	−0.0093 (11)	−0.0034 (10)
C11	0.0860 (16)	0.0687 (14)	0.0814 (14)	−0.0045 (11)	−0.0068 (12)	−0.0010 (11)
O12	0.1166 (13)	0.0812 (11)	0.0849 (10)	−0.0052 (9)	−0.0282 (9)	0.0075 (8)

Geometric parameters (Å, º)

O1—C5	1.334 (2)	C6—H6	0.9300
O1—N2	1.412 (2)	C7—O8	1.364 (2)
N2—C3	1.316 (3)	C7—H7	0.9300
C3—C4	1.417 (3)	O8—C9	1.348 (2)
C3—C6	1.440 (3)	C9—C10	1.308 (3)
C4—C5	1.321 (3)	C9—H9	0.9300
C4—H4	0.9300	C10—C11	1.433 (3)
C5—N5	1.438 (3)	C10—H10	0.9300
N5—O5B	1.217 (2)	C11—O12	1.210 (2)
N5—O5A	1.219 (3)	C11—H11	0.9300
C6—C7	1.307 (3)
C5—O1—N2	106.07 (15)	C7—C6—H6	118.2
C3—N2—O1	106.20 (16)	C3—C6—H6	118.2
N2—C3—C4	111.0 (2)	C6—C7—O8	119.21 (19)
N2—C3—C6	118.29 (18)	C6—C7—H7	120.4
C4—C3—C6	130.67 (18)	O8—C7—H7	120.4
C5—C4—C3	103.30 (18)	C9—O8—C7	120.85 (16)
C5—C4—H4	128.4	C10—C9—O8	129.2 (2)
C3—C4—H4	128.4	C10—C9—H9	115.4
C4—C5—O1	113.39 (19)	O8—C9—H9	115.4
C4—C5—N5	131.7 (2)	C9—C10—C11	119.7 (2)
O1—C5—N5	114.93 (19)	C9—C10—H10	120.1
O5B—N5—O5A	125.4 (2)	C11—C10—H10	120.1
O5B—N5—C5	118.5 (2)	O12—C11—C10	125.2 (2)
O5A—N5—C5	116.1 (2)	O12—C11—H11	117.4
C7—C6—C3	123.54 (19)	C10—C11—H11	117.4

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O12^i	0.93	2.62	3.532 (3)	168
C7—H7···O12^i	0.93	2.44	3.362 (2)	171
C4—H4···O12^i	0.93	2.40	3.282 (3)	159

Symmetry code: (i) −x+2, −y+2, −z+1.