(E)-1-(2-Nitro­ethen­yl)naphthalene

Abstract

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,

• a = 7.2670 (14) Å

• b = 13.741 (3) Å

• c = 19.127 (4) Å

• V = 1909.9 (6) ų

• 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[F ² > 2σ(F ²)] = 0.048

• wR(F ²) = 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

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.

Supplementary Material

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

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) ; (ii) .

supplementary crystallographic information

Comment

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).

Experimental

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.

Refinement

All H atoms were placed in calculated positions, with C-H = 0.95 Å, and refined using a riding model, with U_iso(H) = 1.2U_eq(C).

Figures

Fig. 1.

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

Crystal data

C12H9NO2	F(000) = 832
Mr = 199.20	Dx = 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

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

Refinement

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(Fo2) + (0.0285P)2 + 1.6P] where P = (Fo2 + 2Fc2)/3
2179 reflections	(Δ/σ)max = 0.001
136 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.20 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	0.4804 (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 (Ų)

	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, °)

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, °)

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.