(Z)-1-(3-Nitro­phen­yl)-2-(4-nitro­phen­yl)ethene

Cao, C.; Liu, L.

doi:10.1107/S1600536808021077

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1482

doi:10.1107/S1600536808021077

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(Z)-1-(3-Nitrophenyl)-2-(4-nitrophenyl)ethene

Chenzhong Cao ^a ^* and Liqiu Liu ^a

^aSchool of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, People's Republic of China
^*Correspondence e-mail: chzcao@163.com

(Received 28 June 2008; accepted 8 July 2008; online 12 July 2008)

In the molecule of the title compound, C₁₄H₁₀N₂O₄, the dihedral angle formed by the benzene rings is 53.66 (5)°. In the crystal structure, molecules are linked into chains parallel to the [0 $[\overline{1}]$ 1] direction by intermolecular C—H⋯O hydrogen-bonding interactions.

Related literature

For related literature, see: Boonlaksiri et al. (2000 ); Papper & Likhtenshtein (2001 ); Soto Bustmante et al. (1995 ). For the crystal structure of a related isomer, see: Chen & Cao (2007 ).

Experimental

Crystal data

C₁₄H₁₀N₂O₄
M_r = 270.24
Triclinic, $[P \overline 1]$
a = 7.2995 (13) Å
b = 8.0561 (11) Å
c = 11.831 (2) Å
α = 78.291 (7)°
β = 85.102 (7)°
γ = 67.536 (7)°
V = 629.53 (18) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 296 (2) K
0.50 × 0.24 × 0.19 mm

Data collection

Bruker APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ) T_min = 0.946, T_max = 0.981
4608 measured reflections
2902 independent reflections
2009 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.138
S = 1.03
2902 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯O1ⁱ	0.93	2.56	3.388 (2)	149
Symmetry code: (i) x, y-1, z+1.

Data collection: SMART (Bruker, 2003 ); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808021077/rz2231sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808021077/rz2231Isup2.hkl

checkCIF report

Comment top

Recently, stilbene derivatives have attracted considerable attention from chemists and biologists because of their non-linear optical properties (Soto Bustmante et al., 1995; Papper & Likhtenshtein, 2001) and biological activities (Boonlaksiri et al., 2000). The crystal structure of the related isomer (Z)-1,2-bis(4-nitrophenyl)ethene has been previously reported by our group (Chen & Cao, 2007). We report here the crystal structure of the title compound (Fig. 1), a cis-stilbene derivative.

In the title compound, the C4—C7—C8 and C9—C8—C7 bond angles are 130.11 (16) and 129.92 (15)°, respectively. They are larger than the idealized value of 120° expected for sp²hybrid orbitals due to the comparatively strong stereo hindrance between the two aryl groups. The dihedral angle between the two benzene rings is 53.66 (5)°. The nitro groups at C1 and C11 are slightly twisted out of the plane of the attached benzene rings forming dihedral angles of 7.92 (14) and 9.22 (10)°, respectively. In the crystal structure (Fig. 2), there is non-classical intermolecular C—H···O hydrogen bond (Table 1) linking molecules into chains running parallel to the [0 -1 1] direction.

Related literature top

For related literature, see: Boonlaksiri et al. (2000); Papper & Likhtenshtein (2001); Soto Bustmante et al. (1995). For the crystal structure of a related isomer, see: Chen & Cao (2007).

Experimental top

The title compound was synthesized by the Wittig reaction. Triphenyl(p-nitrobenzyl)phosphonium chloride (0.01 mol), which was obtained by reacting 4-nitrobenzyl chlorine with triphenyl phosphine, and 3-nitrobenzaldehyde (0.01 mol) were dissolved in CH₂Cl₂ (15 ml), then a 50% NaOH solution (4 ml) was titrated into the mixture. The mixture was refluxed for 40 min at 45–50 °C. After cooling to room temperature, water (15 ml) was added and the mixture was extracted with ether (20 ml). The organic layer was washed with water and dried with anhydrous sodium sulfate, then it was filtered and concentrated. The resulting yellow solution was collected and purified by column chromatography on silica gel using petroleum ether and chloroform (10:1 v/v) as eluent (yield: 8.6%). Crystals of the title compound suitable for X-ray analysis were grown by slow evaporation of an ethanol solution. ¹HNMR (CDCl₃)(400 MHz; TMS p.p.m.), δ(p.p.m.): 6.83–6.90 (m, 2H, –C═C–), 7.31–7.54 (m, 4H, Ar), 8.13–8.17 (m, 4H, Ar).

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom-numbering scheme and displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. Packing diagram of the title compound showing intermolecular hydrogen bonds (dashed lines) forming chains parallel to the [0 -1 1] direction.

(Z)-1-(3-Nitrophenyl)-2-(4-nitrophenyl)ethene top

Crystal data top

C₁₄H₁₀N₂O₄	Z = 2
M_r = 270.24	F(000) = 280
Triclinic, P1	D_x = 1.426 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2995 (13) Å	Cell parameters from 1175 reflections
b = 8.0561 (11) Å	θ = 3.5–27.2°
c = 11.831 (2) Å	µ = 0.11 mm⁻¹
α = 78.291 (7)°	T = 296 K
β = 85.102 (7)°	Block, yellow
γ = 67.536 (7)°	0.50 × 0.24 × 0.19 mm
V = 629.53 (18) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	2902 independent reflections
Radiation source: fine-focus sealed tube	2009 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ω scans	θ_max = 27.9°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −9→9
T_min = 0.946, T_max = 0.981	k = −10→9
4608 measured reflections	l = −15→15

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.047	H-atom parameters constrained
wR(F²) = 0.138	w = 1/[σ²(F_o²) + (0.066P)² + 0.0698P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
2902 reflections	Δρ_max = 0.24 e Å⁻³
182 parameters	Δρ_min = −0.19 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.036 (7)

Crystal data top

C₁₄H₁₀N₂O₄	γ = 67.536 (7)°
M_r = 270.24	V = 629.53 (18) Å³
Triclinic, P1	Z = 2
a = 7.2995 (13) Å	Mo Kα radiation
b = 8.0561 (11) Å	µ = 0.11 mm⁻¹
c = 11.831 (2) Å	T = 296 K
α = 78.291 (7)°	0.50 × 0.24 × 0.19 mm
β = 85.102 (7)°

Data collection top

Bruker SMART APEXII CCD diffractometer	2902 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	2009 reflections with I > 2σ(I)
T_min = 0.946, T_max = 0.981	R_int = 0.021
4608 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.138	H-atom parameters constrained
S = 1.03	Δρ_max = 0.24 e Å⁻³
2902 reflections	Δρ_min = −0.19 e Å⁻³
182 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
C11	0.4027 (2)	0.3521 (2)	0.95493 (13)	0.0408 (4)
C10	0.5246 (2)	0.2712 (2)	0.87050 (13)	0.0407 (4)
H10A	0.4941	0.3190	0.7930	0.049*
N2	0.2245 (2)	0.51528 (19)	0.92062 (12)	0.0491 (4)
O4	0.1303 (2)	0.59945 (18)	0.99507 (11)	0.0625 (4)
C9	0.6945 (2)	0.1168 (2)	0.90224 (13)	0.0418 (4)
C14	0.7294 (3)	0.0475 (2)	1.01961 (14)	0.0491 (4)
H14A	0.8396	−0.0581	1.0424	0.059*
C4	0.8254 (2)	0.2702 (2)	0.64805 (13)	0.0445 (4)
C1	0.7410 (2)	0.6180 (2)	0.52136 (13)	0.0437 (4)
N1	0.7019 (2)	0.8008 (2)	0.45317 (13)	0.0553 (4)
C12	0.4397 (3)	0.2862 (2)	1.07097 (14)	0.0509 (4)
H12A	0.3552	0.3448	1.1262	0.061*
O2	0.7283 (2)	0.91400 (19)	0.49721 (13)	0.0734 (4)
O3	0.1784 (2)	0.5610 (2)	0.81952 (12)	0.0804 (5)
C3	0.8289 (3)	0.4109 (2)	0.69887 (14)	0.0518 (4)
H3A	0.8598	0.3868	0.7767	0.062*
C6	0.7387 (3)	0.4823 (2)	0.46765 (14)	0.0490 (4)
H6A	0.7089	0.5071	0.3896	0.059*
C5	0.7812 (2)	0.3098 (2)	0.53140 (14)	0.0485 (4)
H5A	0.7803	0.2174	0.4957	0.058*
C2	0.7876 (3)	0.5846 (2)	0.63620 (14)	0.0509 (4)
H2A	0.7911	0.6773	0.6707	0.061*
C13	0.6048 (3)	0.1315 (3)	1.10274 (14)	0.0547 (5)
H13A	0.6326	0.0834	1.1805	0.066*
C8	0.8307 (3)	0.0184 (2)	0.81795 (15)	0.0511 (4)
H8A	0.8927	−0.1070	0.8429	0.061*
C7	0.8788 (3)	0.0810 (2)	0.71159 (15)	0.0531 (4)
H7A	0.9588	−0.0085	0.6709	0.064*
O1	0.6446 (3)	0.8324 (2)	0.35477 (12)	0.0854 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C11	0.0452 (9)	0.0352 (8)	0.0444 (8)	−0.0183 (7)	0.0008 (6)	−0.0066 (6)
C10	0.0452 (8)	0.0378 (8)	0.0383 (7)	−0.0167 (7)	−0.0026 (6)	−0.0025 (6)
N2	0.0481 (8)	0.0430 (8)	0.0556 (8)	−0.0150 (6)	0.0023 (6)	−0.0129 (7)
O4	0.0606 (8)	0.0543 (8)	0.0711 (8)	−0.0164 (6)	0.0168 (6)	−0.0256 (6)
C9	0.0439 (9)	0.0350 (8)	0.0457 (8)	−0.0163 (7)	−0.0029 (6)	−0.0018 (6)
C14	0.0525 (10)	0.0419 (9)	0.0503 (9)	−0.0207 (8)	−0.0091 (7)	0.0066 (7)
C4	0.0398 (8)	0.0452 (9)	0.0452 (8)	−0.0129 (7)	0.0074 (6)	−0.0104 (7)
C1	0.0399 (8)	0.0440 (9)	0.0449 (8)	−0.0156 (7)	0.0068 (6)	−0.0060 (7)
N1	0.0540 (9)	0.0489 (9)	0.0581 (9)	−0.0181 (7)	0.0067 (7)	−0.0047 (7)
C12	0.0675 (11)	0.0484 (10)	0.0420 (8)	−0.0291 (9)	0.0087 (8)	−0.0086 (7)
O2	0.0851 (11)	0.0496 (8)	0.0885 (10)	−0.0295 (7)	0.0047 (8)	−0.0130 (7)
O3	0.0746 (10)	0.0741 (10)	0.0590 (8)	0.0134 (8)	−0.0155 (7)	−0.0145 (7)
C3	0.0642 (11)	0.0569 (11)	0.0373 (8)	−0.0261 (9)	0.0041 (7)	−0.0105 (7)
C6	0.0498 (10)	0.0544 (10)	0.0416 (8)	−0.0181 (8)	−0.0002 (7)	−0.0095 (7)
C5	0.0512 (10)	0.0495 (10)	0.0476 (9)	−0.0185 (8)	0.0046 (7)	−0.0180 (7)
C2	0.0624 (11)	0.0497 (10)	0.0462 (9)	−0.0260 (8)	0.0092 (7)	−0.0157 (7)
C13	0.0726 (12)	0.0543 (10)	0.0384 (8)	−0.0311 (9)	−0.0056 (8)	0.0053 (7)
C8	0.0503 (10)	0.0353 (8)	0.0586 (10)	−0.0082 (7)	−0.0026 (8)	−0.0035 (7)
C7	0.0526 (10)	0.0427 (9)	0.0556 (10)	−0.0085 (8)	0.0078 (8)	−0.0129 (8)
O1	0.1193 (14)	0.0700 (10)	0.0582 (9)	−0.0343 (9)	−0.0165 (8)	0.0116 (7)

Geometric parameters (Å, º) top

C11—C10	1.372 (2)	C1—N1	1.462 (2)
C11—C12	1.377 (2)	N1—O1	1.2150 (19)
C11—N2	1.467 (2)	N1—O2	1.218 (2)
C10—C9	1.392 (2)	C12—C13	1.374 (3)
C10—H10A	0.9300	C12—H12A	0.9300
N2—O3	1.2143 (18)	C3—C2	1.376 (2)
N2—O4	1.2209 (17)	C3—H3A	0.9300
C9—C14	1.393 (2)	C6—C5	1.371 (2)
C9—C8	1.470 (2)	C6—H6A	0.9300
C14—C13	1.378 (3)	C5—H5A	0.9300
C14—H14A	0.9300	C2—H2A	0.9300
C4—C5	1.389 (2)	C13—H13A	0.9300
C4—C3	1.397 (2)	C8—C7	1.328 (2)
C4—C7	1.473 (2)	C8—H8A	0.9300
C1—C2	1.376 (2)	C7—H7A	0.9300
C1—C6	1.378 (2)

C10—C11—C12	122.86 (15)	C13—C12—C11	118.13 (16)
C10—C11—N2	118.83 (13)	C13—C12—H12A	120.9
C12—C11—N2	118.31 (15)	C11—C12—H12A	120.9
C11—C10—C9	119.22 (14)	C2—C3—C4	121.34 (15)
C11—C10—H10A	120.4	C2—C3—H3A	119.3
C9—C10—H10A	120.4	C4—C3—H3A	119.3
O3—N2—O4	123.14 (15)	C5—C6—C1	118.73 (15)
O3—N2—C11	118.50 (14)	C5—C6—H6A	120.6
O4—N2—C11	118.35 (14)	C1—C6—H6A	120.6
C10—C9—C14	117.92 (15)	C6—C5—C4	121.50 (15)
C10—C9—C8	122.99 (14)	C6—C5—H5A	119.2
C14—C9—C8	118.99 (15)	C4—C5—H5A	119.2
C13—C14—C9	121.71 (16)	C3—C2—C1	118.52 (16)
C13—C14—H14A	119.1	C3—C2—H2A	120.7
C9—C14—H14A	119.1	C1—C2—H2A	120.7
C5—C4—C3	117.99 (15)	C12—C13—C14	120.13 (15)
C5—C4—C7	119.46 (15)	C12—C13—H13A	119.9
C3—C4—C7	122.43 (15)	C14—C13—H13A	119.9
C2—C1—C6	121.91 (15)	C7—C8—C9	129.92 (15)
C2—C1—N1	119.00 (15)	C7—C8—H8A	115.0
C6—C1—N1	119.03 (15)	C9—C8—H8A	115.0
O1—N1—O2	123.13 (16)	C8—C7—C4	130.11 (16)
O1—N1—C1	118.13 (16)	C8—C7—H7A	114.9
O2—N1—C1	118.75 (15)	C4—C7—H7A	114.9

C12—C11—C10—C9	−0.7 (2)	C7—C4—C3—C2	176.81 (16)
N2—C11—C10—C9	179.75 (13)	C2—C1—C6—C5	1.0 (3)
C10—C11—N2—O3	8.4 (2)	N1—C1—C6—C5	178.16 (14)
C12—C11—N2—O3	−171.23 (16)	C1—C6—C5—C4	0.2 (3)
C10—C11—N2—O4	−171.07 (14)	C3—C4—C5—C6	−1.1 (2)
C12—C11—N2—O4	9.3 (2)	C7—C4—C5—C6	−177.24 (16)
C11—C10—C9—C14	2.1 (2)	C4—C3—C2—C1	0.4 (3)
C11—C10—C9—C8	178.34 (14)	C6—C1—C2—C3	−1.3 (3)
C10—C9—C14—C13	−2.3 (2)	N1—C1—C2—C3	−178.45 (16)
C8—C9—C14—C13	−178.65 (16)	C11—C12—C13—C14	0.6 (3)
C2—C1—N1—O1	−173.84 (17)	C9—C14—C13—C12	0.9 (3)
C6—C1—N1—O1	8.9 (2)	C10—C9—C8—C7	32.4 (3)
C2—C1—N1—O2	6.3 (2)	C14—C9—C8—C7	−151.46 (19)
C6—C1—N1—O2	−170.93 (15)	C9—C8—C7—C4	6.1 (3)
C10—C11—C12—C13	−0.8 (3)	C5—C4—C7—C8	−140.7 (2)
N2—C11—C12—C13	178.83 (14)	C3—C4—C7—C8	43.3 (3)
C5—C4—C3—C2	0.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···O1ⁱ	0.93	2.56	3.388 (2)	149

Symmetry code: (i) x, y−1, z+1.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₀N₂O₄
M_r	270.24
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.2995 (13), 8.0561 (11), 11.831 (2)
α, β, γ (°)	78.291 (7), 85.102 (7), 67.536 (7)
V (Å³)	629.53 (18)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.50 × 0.24 × 0.19

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2002)
T_min, T_max	0.946, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	4608, 2902, 2009
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.138, 1.03
No. of reflections	2902
No. of parameters	182
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.19

Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···O1ⁱ	0.93	2.56	3.388 (2)	148.6

Symmetry code: (i) x, y−1, z+1.

Acknowledgements

The project was supported by the National Natural Science Foundation of China (NSFC) (No. 20772028) and the Natural Science Foundation of Hunan Province (NSFH) (No. 06JJ2002)

References

Boonlaksiri, C., Oonanant, W., Kongsaeree, P., Kittakoop, P., Tanticharoen, M. & &Thebtaranonth, Y. (2000). Phytochemistry, 54, 415–417. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2003). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, C. & Cao, C. (2007). Acta Cryst. E63, o3999–o4000. Web of Science CSD CrossRef IUCr Journals Google Scholar
Papper, V. & Likhtenshtein, G. I. (2001). J. Photochem. Photobiol. A, 140, 39–52. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2002). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Soto Bustamante, E. A., Hanemann, T., Haase, W., Svoboda, I. & Fuess, H. (1995). Acta Cryst. C51, 2192–2196. CSD CrossRef IUCr Journals Google Scholar