(E)-1-(2-Nitro­ethen­yl)naphthalene

Jing, L.-H.

doi:10.1107/S1600536809037623

organic compounds

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Volume 65| Part 10| October 2009| Page o2521

doi:10.1107/S1600536809037623

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(E)-1-(2-Nitroethenyl)naphthalene

Lin-Hai Jing ^a ^*

^aSchool of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, People's Republic of China
^*Correspondence e-mail: jlhjhr@yahoo.com.cn

(Received 16 September 2009; accepted 17 September 2009; online 26 September 2009)

The title molecule, C₁₂H₉NO₂, adopts a trans configuration about the olefinic double bond. The dihedral angle between the naphthalene ring system (r.m.s. deviation = 0.012 Å) and the nitroethenyl group (r.m.s. deviation = 0.032 Å) is 12.66 (5)°. The molecules are linked into a two-dimensional network parallel to the bc plane by C—H⋯O hydrogen bonds. The substituted benzene rings in adjacent networks are stacked with a centroid–centroid distance of 3.6337 (11) Å, indicating π–π interactions.

Related literature

For general background to β-nitroolefins, see: Barrett & Graboski (1986 ). For the synthesis, see: Cheng et al. (2007 ).

Experimental

Crystal data

C₁₂H₉NO₂
M_r = 199.20
Orthorhombic, P b c a
a = 7.2670 (14) Å
b = 13.741 (3) Å
c = 19.127 (4) Å
V = 1909.9 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 93 K
0.40 × 0.33 × 0.13 mm

Data collection

Rigaku SPIDER diffractometer
Absorption correction: none
14290 measured reflections
2179 independent reflections
2019 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.099
S = 1.00
2179 reflections
136 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O2ⁱ	0.95	2.58	3.3919 (19)	144
C7—H7⋯O2ⁱⁱ	0.95	2.52	3.4261 (19)	159
C12—H12⋯O2ⁱ	0.95	2.57	3.464 (2)	158
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: RAPID-AUTO (Rigaku/MSC, 2004 ); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809037623/ci2915sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809037623/ci2915Isup2.hkl

checkCIF report

Comment top

β-Nitroolefins are a class of useful and versatile building blocks in organic synthesis (Barrett & Graboski, 1986). The author reports here, the crystal structure of the title compound.

Bond lengths and angles in the title molecule are normal. The molecule adopts a trans configuration about the olefinic double bond (Fig. 1). The naphthalene ring system is planar, with a maximum deviation of 0.021 (1) Å for atom C1. The dihedral angle between the C1-C9 and N1/O1/O2/C11/C12 planes is 12.66 (5)°. The molecules are linked into a two-dimensional network parallel to the bc plane by C—H···O hydrogen bonds (Table 1).

Related literature top

For general background to β-nitroolefins, see: Barrett & Graboski (1986). For the synthesis, see: Cheng et al. (2007).

Experimental top

The title compound was synthesized according to the method reported in the literature (Cheng et al., 2007). Yellow single crystals suitable for X-ray diffraction were obtained by slow evaporation of a methanol solution.

Computing details top

Data collection: RAPID-AUTO (Rigaku/MSC, 2004); cell refinement: RAPID-AUTO (Rigaku/MSC, 2004); data reduction: RAPID-AUTO (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering.

(E)-1-(2-Nitroethenyl)naphthalene top

Crystal data top

C₁₂H₉NO₂	F(000) = 832
M_r = 199.20	D_x = 1.386 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5654 reflections
a = 7.2670 (14) Å	θ = 3.0–27.5°
b = 13.741 (3) Å	µ = 0.10 mm⁻¹
c = 19.127 (4) Å	T = 93 K
V = 1909.9 (6) Å³	Prism, yellow
Z = 8	0.40 × 0.33 × 0.13 mm

Data collection top

Rigaku SPIDER diffractometer	2019 reflections with I > 2σ(I)
Radiation source: Rotating anode	R_int = 0.030
Graphite monochromator	θ_max = 27.5°, θ_min = 3.2°
ω scans	h = −9→9
14290 measured reflections	k = −17→17
2179 independent reflections	l = −24→24

Refinement top

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) = 0.099	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0285P)² + 1.6P] where P = (F_o² + 2F_c²)/3
2179 reflections	(Δ/σ)_max = 0.001
136 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₂H₉NO₂	V = 1909.9 (6) Å³
M_r = 199.20	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 7.2670 (14) Å	µ = 0.10 mm⁻¹
b = 13.741 (3) Å	T = 93 K
c = 19.127 (4) Å	0.40 × 0.33 × 0.13 mm

Data collection top

Rigaku SPIDER diffractometer	2019 reflections with I > 2σ(I)
14290 measured reflections	R_int = 0.030
2179 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.099	H-atom parameters constrained
S = 1.00	Δρ_max = 0.30 e Å⁻³
2179 reflections	Δρ_min = −0.20 e Å⁻³
136 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.4804 (2)	0.25001 (8)	0.56207 (6)	0.0438 (4)
O2	0.4755 (2)	0.35241 (8)	0.47651 (6)	0.0414 (3)
N1	0.50070 (19)	0.33185 (9)	0.53854 (6)	0.0270 (3)
C1	0.61925 (19)	0.47388 (10)	0.70231 (7)	0.0193 (3)
C2	0.67974 (19)	0.56401 (10)	0.67959 (8)	0.0216 (3)
H2	0.6907	0.5759	0.6308	0.026*
C3	0.7251 (2)	0.63794 (10)	0.72673 (8)	0.0233 (3)
H3	0.7665	0.6991	0.7097	0.028*
C4	0.7103 (2)	0.62294 (10)	0.79730 (8)	0.0237 (3)
H4	0.7403	0.6740	0.8288	0.028*
C5	0.6346 (2)	0.51571 (11)	0.89674 (8)	0.0250 (3)
H5	0.6628	0.5669	0.9283	0.030*
C6	0.5794 (2)	0.42761 (11)	0.92232 (8)	0.0260 (3)
H6	0.5693	0.4178	0.9713	0.031*
C7	0.5373 (2)	0.35112 (11)	0.87574 (8)	0.0246 (3)
H7	0.5001	0.2897	0.8936	0.030*
C8	0.5497 (2)	0.36480 (10)	0.80489 (7)	0.0216 (3)
H8	0.5198	0.3126	0.7744	0.026*
C9	0.60624 (18)	0.45543 (9)	0.77616 (7)	0.0189 (3)
C10	0.65057 (19)	0.53203 (10)	0.82360 (8)	0.0204 (3)
C11	0.5682 (2)	0.39854 (10)	0.65200 (7)	0.0219 (3)
H11	0.5419	0.3356	0.6700	0.026*
C12	0.5554 (2)	0.41047 (11)	0.58392 (8)	0.0278 (3)
H12	0.5829	0.4723	0.5642	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0825 (10)	0.0188 (5)	0.0300 (6)	−0.0081 (6)	0.0015 (6)	−0.0001 (5)
O2	0.0744 (10)	0.0281 (6)	0.0216 (6)	−0.0004 (6)	−0.0060 (6)	−0.0006 (5)
N1	0.0370 (7)	0.0208 (6)	0.0231 (6)	0.0009 (6)	0.0016 (5)	−0.0004 (5)
C1	0.0165 (6)	0.0179 (6)	0.0236 (7)	0.0030 (5)	−0.0002 (5)	0.0002 (5)
C2	0.0190 (7)	0.0218 (7)	0.0241 (7)	0.0022 (5)	−0.0003 (5)	0.0033 (6)
C3	0.0191 (7)	0.0169 (6)	0.0339 (8)	−0.0018 (5)	−0.0003 (6)	0.0030 (6)
C4	0.0209 (7)	0.0195 (6)	0.0306 (8)	0.0003 (5)	−0.0013 (6)	−0.0041 (6)
C5	0.0242 (7)	0.0255 (7)	0.0252 (7)	0.0034 (6)	−0.0003 (6)	−0.0054 (6)
C6	0.0281 (8)	0.0285 (7)	0.0214 (7)	0.0056 (6)	0.0031 (6)	0.0010 (6)
C7	0.0259 (7)	0.0209 (7)	0.0270 (7)	0.0040 (6)	0.0052 (6)	0.0048 (6)
C8	0.0223 (7)	0.0174 (6)	0.0250 (7)	0.0030 (5)	0.0011 (6)	−0.0002 (5)
C9	0.0147 (6)	0.0175 (6)	0.0245 (7)	0.0038 (5)	0.0009 (5)	−0.0001 (5)
C10	0.0157 (6)	0.0200 (7)	0.0255 (7)	0.0030 (5)	−0.0002 (5)	−0.0014 (5)
C11	0.0242 (7)	0.0167 (6)	0.0249 (7)	0.0021 (5)	0.0003 (6)	0.0016 (5)
C12	0.0389 (9)	0.0185 (7)	0.0260 (7)	−0.0042 (6)	−0.0012 (7)	−0.0003 (6)

Geometric parameters (Å, º) top

O1—N1	1.2201 (17)	C5—C10	1.422 (2)
O2—N1	1.2335 (16)	C5—H5	0.95
N1—C12	1.4417 (19)	C6—C7	1.411 (2)
C1—C2	1.3841 (19)	C6—H6	0.95
C1—C9	1.4381 (19)	C7—C8	1.371 (2)
C1—C11	1.4613 (19)	C7—H7	0.95
C2—C3	1.398 (2)	C8—C9	1.4220 (19)
C2—H2	0.95	C8—H8	0.95
C3—C4	1.370 (2)	C9—C10	1.4265 (19)
C3—H3	0.95	C11—C12	1.316 (2)
C4—C10	1.415 (2)	C11—H11	0.95
C4—H4	0.95	C12—H12	0.95
C5—C6	1.366 (2)

O1—N1—O2	123.23 (13)	C7—C6—H6	120.1
O1—N1—C12	120.13 (13)	C8—C7—C6	120.51 (14)
O2—N1—C12	116.64 (12)	C8—C7—H7	119.7
C2—C1—C9	119.15 (13)	C6—C7—H7	119.7
C2—C1—C11	120.51 (13)	C7—C8—C9	121.40 (13)
C9—C1—C11	120.34 (12)	C7—C8—H8	119.3
C1—C2—C3	121.50 (13)	C9—C8—H8	119.3
C1—C2—H2	119.3	C8—C9—C10	117.75 (13)
C3—C2—H2	119.3	C8—C9—C1	123.58 (13)
C4—C3—C2	120.52 (13)	C10—C9—C1	118.67 (13)
C4—C3—H3	119.7	C4—C10—C5	120.94 (13)
C2—C3—H3	119.7	C4—C10—C9	119.65 (13)
C3—C4—C10	120.48 (13)	C5—C10—C9	119.42 (13)
C3—C4—H4	119.8	C12—C11—C1	125.55 (13)
C10—C4—H4	119.8	C12—C11—H11	117.2
C6—C5—C10	121.07 (14)	C1—C11—H11	117.2
C6—C5—H5	119.5	C11—C12—N1	121.46 (14)
C10—C5—H5	119.5	C11—C12—H12	119.3
C5—C6—C7	119.84 (14)	N1—C12—H12	119.3
C5—C6—H6	120.1

C9—C1—C2—C3	−1.2 (2)	C3—C4—C10—C5	−179.96 (14)
C11—C1—C2—C3	178.42 (13)	C3—C4—C10—C9	0.2 (2)
C1—C2—C3—C4	−0.1 (2)	C6—C5—C10—C4	−179.12 (14)
C2—C3—C4—C10	0.6 (2)	C6—C5—C10—C9	0.7 (2)
C10—C5—C6—C7	0.0 (2)	C8—C9—C10—C4	179.02 (12)
C5—C6—C7—C8	−0.7 (2)	C1—C9—C10—C4	−1.6 (2)
C6—C7—C8—C9	0.5 (2)	C8—C9—C10—C5	−0.79 (19)
C7—C8—C9—C10	0.2 (2)	C1—C9—C10—C5	178.64 (13)
C7—C8—C9—C1	−179.20 (14)	C2—C1—C11—C12	−7.4 (2)
C2—C1—C9—C8	−178.57 (13)	C9—C1—C11—C12	172.20 (15)
C11—C1—C9—C8	1.8 (2)	C1—C11—C12—N1	−178.90 (14)
C2—C1—C9—C10	2.03 (19)	O1—N1—C12—C11	−6.4 (2)
C11—C1—C9—C10	−177.61 (12)	O2—N1—C12—C11	173.19 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2ⁱ	0.95	2.58	3.3919 (19)	144
C7—H7···O2ⁱⁱ	0.95	2.52	3.4261 (19)	159
C12—H12···O2ⁱ	0.95	2.57	3.464 (2)	158

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

Experimental details

Crystal data
Chemical formula	C₁₂H₉NO₂
M_r	199.20
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	93
a, b, c (Å)	7.2670 (14), 13.741 (3), 19.127 (4)
V (Å³)	1909.9 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.40 × 0.33 × 0.13

Data collection
Diffractometer	Rigaku SPIDER diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	14290, 2179, 2019
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.099, 1.00
No. of reflections	2179
No. of parameters	136
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.20

Computer programs: RAPID-AUTO (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2ⁱ	0.95	2.58	3.3919 (19)	144
C7—H7···O2ⁱⁱ	0.95	2.52	3.4261 (19)	159
C12—H12···O2ⁱ	0.95	2.57	3.464 (2)	158

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

Acknowledgements

The author thanks the Centre for Testing and Analysis, Cheng Du Branch, Chinese Academy of Sciences, for analytical support.

References

Barrett, A. G. M. & Graboski, G. G. (1986). Chem. Rev. 86, 751–762. CrossRef CAS Web of Science Google Scholar
Cheng, P., Jiang, Z. Y., Wang, R. R., Zhang, X. M., Wang, Q., Zheng, Y. T., Zhou, J. & Chen, J. J. (2007). Bioorg. Med. Chem. Lett. 17, 4476–4480. Web of Science CrossRef PubMed CAS Google Scholar
Rigaku/MSC (2004). RAPID-AUTO. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar