2-(4-Nitro­phen­yl)-5-phenyl­furan

Guan, Z.; He, Y.; Wang, G.

doi:10.1107/S160053680905288X

organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o128

doi:10.1107/S160053680905288X

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2-(4-Nitrophenyl)-5-phenylfuran

Zhi Guan,^a Yan-hong He ^a ^* and Gangqiang Wang ^a

^aSchool of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, People's Republic of China
^*Correspondence e-mail: heyh@swu.edu.cn

(Received 23 November 2009; accepted 9 December 2009; online 12 December 2009)

The molecular skeleton of the title molecule, C₁₆H₁₁NO₃, is nearly planar with the two aromatic rings forming a dihedral angle of 2.73 (7)°. In the crystal, weak intermolecular C—H⋯O hydrogen bonds link molecules into ribbons extended along [101]. The crystal packing exhibits also π–π interactions, as indicated by the short centroid–centroid distances between the aromatic rings [3.681 (3) Å] and between the aromatic and furan rings [3.811 (3) Å] of neighbouring molecules.

Related literature

For details of the synthesis, see: Wang et al. (2009 ).

Experimental

Crystal data

C₁₆H₁₁NO₃
M_r = 265.26
Monoclinic, P 2₁ /n
a = 7.3213 (15) Å
b = 16.290 (3) Å
c = 10.904 (2) Å
β = 100.81 (3)°
V = 1277.3 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 113 K
0.24 × 0.22 × 0.19 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.977, T_max = 0.982
10136 measured reflections
2924 independent reflections
1168 reflections with I > 2σ(I)
R_int = 0.070

Refinement

R[F² > 2σ(F²)] = 0.063
wR(F²) = 0.174
S = 1.00
2924 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.22 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
C3—H3⋯O3ⁱ	0.95	2.51	3.373 (3)	152
C12—H12⋯O2ⁱⁱ	0.95	2.61	3.435 (3)	146
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) x+1, y, z+1.

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680905288X/cv2666sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680905288X/cv2666Isup2.hkl

checkCIF report

Comment top

The title compound, (I), has been obtained as a by-product in our ongoing research of highly substituted furan derivatives (Wang et al., 2009).

In (I) (Fig. 1), two aromatic rings form a dihedral angle of 2.73 (7) °. Weak intermolecular C—H···O hydrogen bonds (Table 1) and π-π stacking interactions with centroid-centroid separations of 3.681 (3) and 3.811 (3) Å consolidate the crystal packing.

Related literature top

For details of the synthesis, see: Wang et al. (2009).

Experimental top

A solution of ethyl 2-benzoyl-4-(4-nitrophenyl)-4-oxobutanoate (0.353 g, 0.7 mmol) in ionic liquid [bmim]HSO₄(1.6 g, 6.7 mmol) was stirred at 150 °C for 4 h in oil bath. After cooling to r.t., the reaction mixture was extracted with diethyl ether thoroughly. The combined extracts were washed with water, brine,dried (Na₂SO₄),and filtered. The solvents were removed and the residue was purified by flash chromatography (petroleum ether / dichloromethane 2:1) to get Ethyl 5-(4-nitrophenyl)-2-phenylfuran-3-carboxylate (240 mg, 71%) and the title compound (50 mg,14%) as yellow crystals.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

2-(4-Nitrophenyl)-5-phenylfuran top

Crystal data top

C₁₆H₁₁NO₃	F(000) = 552
M_r = 265.26	D_x = 1.379 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.3213 (15) Å	Cell parameters from 3226 reflections
b = 16.290 (3) Å	θ = 2.3–27.7°
c = 10.904 (2) Å	µ = 0.10 mm⁻¹
β = 100.81 (3)°	T = 113 K
V = 1277.3 (4) Å³	Block, orange
Z = 4	0.24 × 0.22 × 0.19 mm

Data collection top

Rigaku Saturn CCD area-detector diffractometer	2924 independent reflections
Radiation source: rotating anode	1168 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.070
Detector resolution: 7.31 pixels mm^-1	θ_max = 27.6°, θ_min = 3.1°
ω and ϕ scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −21→21
T_min = 0.977, T_max = 0.982	l = −12→14
10136 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.063	w = 1/[σ²(F_o²) + (0.0654P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.174	(Δ/σ)_max < 0.001
S = 1.00	Δρ_max = 0.22 e Å⁻³
2924 reflections	Δρ_min = −0.19 e Å⁻³
182 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.086 (10)
Secondary atom site location: difference Fourier map

Crystal data top

C₁₆H₁₁NO₃	V = 1277.3 (4) Å³
M_r = 265.26	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.3213 (15) Å	µ = 0.10 mm⁻¹
b = 16.290 (3) Å	T = 113 K
c = 10.904 (2) Å	0.24 × 0.22 × 0.19 mm
β = 100.81 (3)°

Data collection top

Rigaku Saturn CCD area-detector diffractometer	2924 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	1168 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.982	R_int = 0.070
10136 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	182 parameters
wR(F²) = 0.174	H-atom parameters constrained
S = 1.00	Δρ_max = 0.22 e Å⁻³
2924 reflections	Δρ_min = −0.19 e Å⁻³

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	0.83658 (18)	0.47058 (7)	0.09998 (13)	0.0540 (5)
O2	0.3323 (3)	0.56325 (12)	−0.48419 (15)	0.0968 (7)
O3	0.3467 (3)	0.69148 (10)	−0.43913 (17)	0.0971 (7)
N1	0.3792 (3)	0.61960 (13)	−0.41169 (19)	0.0685 (6)
C1	0.4782 (3)	0.60055 (13)	−0.2862 (2)	0.0528 (6)
C2	0.5230 (3)	0.66262 (13)	−0.2022 (2)	0.0632 (7)
H2	0.4856	0.7174	−0.2240	0.076*
C3	0.6219 (3)	0.64521 (13)	−0.0866 (2)	0.0612 (7)
H3	0.6524	0.6882	−0.0275	0.073*
C4	0.6791 (3)	0.56563 (12)	−0.05378 (19)	0.0504 (6)
C5	0.6301 (3)	0.50391 (12)	−0.1400 (2)	0.0569 (6)
H5	0.6657	0.4489	−0.1185	0.068*
C6	0.5298 (3)	0.52119 (12)	−0.2572 (2)	0.0595 (6)
H6	0.4971	0.4787	−0.3169	0.071*
C7	0.7901 (3)	0.55033 (12)	0.0684 (2)	0.0554 (6)
C9	0.9599 (3)	0.54956 (13)	0.2595 (2)	0.0696 (8)
H9	1.0268	0.5672	0.3382	0.084*
C8	0.8639 (3)	0.59996 (14)	0.1642 (2)	0.0700 (8)
H8	0.8530	0.6580	0.1666	0.084*
C10	0.9392 (3)	0.47133 (13)	0.2184 (2)	0.0547 (6)
C11	1.0059 (3)	0.39286 (13)	0.2725 (2)	0.0552 (6)
C12	1.0985 (3)	0.38948 (14)	0.3963 (2)	0.0673 (7)
H12	1.1158	0.4382	0.4450	0.081*
C13	1.1648 (3)	0.31612 (15)	0.4481 (2)	0.0787 (8)
H13	1.2278	0.3145	0.5326	0.094*
C14	1.1415 (4)	0.24587 (16)	0.3802 (3)	0.0848 (9)
H14	1.1872	0.1953	0.4173	0.102*
C15	1.0523 (4)	0.24782 (14)	0.2581 (3)	0.0847 (9)
H15	1.0371	0.1986	0.2104	0.102*
C16	0.9841 (3)	0.32104 (13)	0.2038 (2)	0.0683 (7)
H16	0.9221	0.3220	0.1191	0.082*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0608 (9)	0.0479 (9)	0.0501 (10)	0.0013 (7)	0.0021 (8)	0.0039 (7)
O2	0.1211 (16)	0.0947 (14)	0.0616 (12)	0.0146 (11)	−0.0160 (11)	−0.0143 (10)
O3	0.1200 (16)	0.0727 (13)	0.0855 (14)	0.0136 (10)	−0.0141 (12)	0.0234 (10)
N1	0.0684 (13)	0.0728 (14)	0.0594 (14)	0.0080 (10)	−0.0007 (11)	0.0052 (11)
C1	0.0501 (12)	0.0567 (13)	0.0489 (13)	0.0029 (10)	0.0023 (10)	0.0059 (10)
C2	0.0694 (15)	0.0474 (13)	0.0655 (16)	0.0056 (11)	−0.0063 (12)	0.0013 (11)
C3	0.0701 (15)	0.0471 (13)	0.0605 (15)	0.0021 (10)	−0.0031 (12)	−0.0038 (11)
C4	0.0537 (13)	0.0457 (12)	0.0507 (13)	−0.0042 (9)	0.0072 (10)	0.0037 (10)
C5	0.0726 (15)	0.0420 (12)	0.0540 (14)	0.0031 (10)	0.0063 (12)	0.0040 (10)
C6	0.0739 (16)	0.0502 (13)	0.0516 (14)	−0.0001 (10)	0.0048 (12)	−0.0039 (10)
C7	0.0614 (13)	0.0468 (12)	0.0547 (14)	0.0027 (10)	0.0029 (11)	0.0032 (10)
C9	0.0815 (17)	0.0579 (15)	0.0600 (15)	−0.0001 (12)	−0.0111 (13)	−0.0044 (12)
C8	0.0825 (17)	0.0520 (14)	0.0660 (16)	0.0046 (12)	−0.0102 (13)	−0.0033 (12)
C10	0.0535 (13)	0.0579 (14)	0.0484 (14)	−0.0008 (10)	−0.0015 (11)	0.0047 (10)
C11	0.0484 (12)	0.0554 (13)	0.0588 (15)	−0.0014 (10)	0.0023 (11)	0.0082 (11)
C12	0.0727 (16)	0.0644 (15)	0.0594 (16)	0.0006 (12)	−0.0015 (13)	0.0066 (12)
C13	0.0857 (18)	0.0737 (18)	0.0680 (18)	0.0021 (14)	−0.0076 (15)	0.0174 (14)
C14	0.100 (2)	0.0590 (16)	0.087 (2)	0.0009 (14)	−0.0049 (17)	0.0195 (14)
C15	0.106 (2)	0.0523 (15)	0.087 (2)	−0.0018 (13)	−0.0051 (17)	0.0046 (14)
C16	0.0772 (16)	0.0555 (14)	0.0641 (16)	−0.0037 (12)	−0.0074 (13)	0.0029 (12)

Geometric parameters (Å, º) top

O1—C10	1.367 (2)	C9—C10	1.350 (3)
O1—C7	1.371 (2)	C9—C8	1.405 (3)
O2—N1	1.218 (2)	C9—H9	0.9500
O3—N1	1.221 (2)	C8—H8	0.9500
N1—C1	1.457 (3)	C10—C11	1.453 (3)
C1—C2	1.363 (3)	C11—C16	1.382 (3)
C1—C6	1.367 (3)	C11—C12	1.394 (3)
C2—C3	1.360 (3)	C12—C13	1.371 (3)
C2—H2	0.9500	C12—H12	0.9500
C3—C4	1.388 (3)	C13—C14	1.357 (3)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.377 (3)	C14—C15	1.369 (3)
C4—C7	1.446 (3)	C14—H14	0.9500
C5—C6	1.379 (3)	C15—C16	1.382 (3)
C5—H5	0.9500	C15—H15	0.9500
C6—H6	0.9500	C16—H16	0.9500
C7—C8	1.351 (3)

C10—O1—C7	107.20 (15)	C10—C9—H9	126.4
O2—N1—O3	123.0 (2)	C8—C9—H9	126.4
O2—N1—C1	118.64 (19)	C7—C8—C9	107.1 (2)
O3—N1—C1	118.31 (19)	C7—C8—H8	126.4
C2—C1—C6	121.7 (2)	C9—C8—H8	126.4
C2—C1—N1	119.23 (19)	C9—C10—O1	109.24 (17)
C6—C1—N1	119.06 (19)	C9—C10—C11	133.4 (2)
C3—C2—C1	119.2 (2)	O1—C10—C11	117.31 (18)
C3—C2—H2	120.4	C16—C11—C12	118.48 (19)
C1—C2—H2	120.4	C16—C11—C10	122.0 (2)
C2—C3—C4	121.1 (2)	C12—C11—C10	119.55 (19)
C2—C3—H3	119.5	C13—C12—C11	120.3 (2)
C4—C3—H3	119.5	C13—C12—H12	119.9
C5—C4—C3	118.56 (19)	C11—C12—H12	119.9
C5—C4—C7	122.16 (18)	C14—C13—C12	120.8 (2)
C3—C4—C7	119.27 (18)	C14—C13—H13	119.6
C4—C5—C6	120.60 (19)	C12—C13—H13	119.6
C4—C5—H5	119.7	C13—C14—C15	120.0 (2)
C6—C5—H5	119.7	C13—C14—H14	120.0
C1—C6—C5	118.91 (19)	C15—C14—H14	120.0
C1—C6—H6	120.5	C14—C15—C16	120.3 (2)
C5—C6—H6	120.5	C14—C15—H15	119.9
C8—C7—O1	109.16 (18)	C16—C15—H15	119.9
C8—C7—C4	133.11 (19)	C11—C16—C15	120.2 (2)
O1—C7—C4	117.73 (17)	C11—C16—H16	119.9
C10—C9—C8	107.3 (2)	C15—C16—H16	119.9

O2—N1—C1—C2	−176.6 (2)	O1—C7—C8—C9	−0.1 (3)
O3—N1—C1—C2	3.1 (3)	C4—C7—C8—C9	−179.7 (2)
O2—N1—C1—C6	5.8 (3)	C10—C9—C8—C7	−0.6 (3)
O3—N1—C1—C6	−174.4 (2)	C8—C9—C10—O1	1.0 (3)
C6—C1—C2—C3	0.2 (4)	C8—C9—C10—C11	179.3 (2)
N1—C1—C2—C3	−177.37 (19)	C7—O1—C10—C9	−1.1 (2)
C1—C2—C3—C4	0.6 (4)	C7—O1—C10—C11	−179.68 (19)
C2—C3—C4—C5	−1.4 (3)	C9—C10—C11—C16	−171.6 (2)
C2—C3—C4—C7	177.7 (2)	O1—C10—C11—C16	6.5 (3)
C3—C4—C5—C6	1.4 (3)	C9—C10—C11—C12	6.9 (4)
C7—C4—C5—C6	−177.6 (2)	O1—C10—C11—C12	−174.98 (19)
C2—C1—C6—C5	−0.2 (4)	C16—C11—C12—C13	−0.4 (4)
N1—C1—C6—C5	177.36 (19)	C10—C11—C12—C13	−179.0 (2)
C4—C5—C6—C1	−0.6 (4)	C11—C12—C13—C14	0.0 (4)
C10—O1—C7—C8	0.8 (2)	C12—C13—C14—C15	0.5 (4)
C10—O1—C7—C4	−179.61 (18)	C13—C14—C15—C16	−0.6 (4)
C5—C4—C7—C8	175.4 (2)	C12—C11—C16—C15	0.4 (4)
C3—C4—C7—C8	−3.6 (4)	C10—C11—C16—C15	178.9 (2)
C5—C4—C7—O1	−4.1 (3)	C14—C15—C16—C11	0.1 (4)
C3—C4—C7—O1	176.93 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3ⁱ	0.95	2.51	3.373 (3)	152
C12—H12···O2ⁱⁱ	0.95	2.61	3.435 (3)	146

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₁NO₃
M_r	265.26
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	113
a, b, c (Å)	7.3213 (15), 16.290 (3), 10.904 (2)
β (°)	100.81 (3)
V (Å³)	1277.3 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.24 × 0.22 × 0.19

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.977, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	10136, 2924, 1168
R_int	0.070
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.174, 1.00
No. of reflections	2924
No. of parameters	182
No. of restraints	?
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.19

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3ⁱ	0.95	2.51	3.373 (3)	151.9
C12—H12···O2ⁱⁱ	0.95	2.61	3.435 (3)	145.9

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

Acknowledgements

This work was funded in 2007 as a selected project in scientific and technological activities for returned scholars by the State Personnel Ministry.

References

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