2-(2-Meth­oxy­phen­yl)-1-benzofuran

Pojarová, M.; Dušek, M.; Jančařík, A.; Makrlík, E.; Sedláková, Z.

doi:10.1107/S1600536811017168

organic compounds

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Volume 67| Part 6| June 2011| Page o1427

doi:10.1107/S1600536811017168

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2-(2-Methoxyphenyl)-1-benzofuran

Michaela Pojarová,^a ^* Michal Dušek,^a Andrej Jančařík,^b Emanuel Makrlík ^c and Zdeňka Sedláková ^d

^aInstitute of Physics, AS CR, v.v.i., Na Slovance 2, 182 21 Prague 8, Czech Republic, ^bInstitute of Organic Chemistry and Biochemistry of AS CR, Fleming sq. 2, 166 10 Prague 6, Czech Republic, ^cFaculty of Applied Sciences, University of West Bohemia, Husova 11, 306 14 Pilsen, Czech Republic, and ^dInstitue od Macromolecular Chemistry of AS CR, Heyrovský sq. 2, 162 06 Prague 6, Czech Republic
^*Correspondence e-mail: pojarova@fzu.cz

(Received 29 April 2011; accepted 6 May 2011; online 14 May 2011)

In the title compound, C₁₅H₁₂O₂, the dihedral angle between the aromatic ring systems is 16.67 (6)°. The methyl C atom is almost coplanar with its attached benzene ring [displacement = 0.020 (2) Å]. In the crystal, the molecules are connected by weak C—H⋯O bonds and face-to-edge C—H⋯π interactions between the 2-methoxyphenyl rings.

Related literature

For the biological activity of related compounds, see: Akgul & Anil (2003 ); Aslam et al. (2006 ); Galal et al. (2009 ); Khan et al. (2005 ); Soekamto et al. (2003 ). For the synthesis, see: Takeda et al. (2007 ).

Experimental

Crystal data

C₁₅H₁₂O₂
M_r = 224.25
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.9419 (1) Å
b = 11.4409 (2) Å
c = 14.1703 (3) Å
V = 1125.43 (3) Å³
Z = 4
Cu Kα radiation
μ = 0.70 mm⁻¹
T = 120 K
0.27 × 0.25 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur Atlas Gemini Ultra diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.683, T_max = 1.000
11347 measured reflections
2006 independent reflections
1955 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.088
S = 1.09
2006 reflections
155 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.14 e Å⁻³
Absolute structure: Flack (1983 ), 822 Friedel pairs
Flack parameter: −0.2 (2)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1B⋯O2ⁱ	0.96	2.57	3.272 (2)	131
C3—H3⋯Cg1ⁱⁱ	0.93	2.78	3.604 (2)	149
Symmetry codes: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811017168/hb5866sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811017168/hb5866Isup2.hkl

checkCIF report

Comment top

A wide range of natural products with diverse pharmaceutical properties, such as antifungal, antitumor, antiviral, and antimicrobial (Aslam et al., 2006; Galal et al., 2009; Khan et al., 2005), contain a benzofuran ring (Akgul & Anil, 2003; Soekamto et al., 2003). In this paper, we present a crystal structure of the title compound, (I).

The benzofuran unit is essentially planar, with a mean deviation of 0.019 (2)Å from the least-square plane defined by the nine atoms in benzofuran ring. The methoxy group forms intermolecular hydrogen bond to the oxygen in benzofuran ring (Table 1). Another weak interactions found in the crystal is the C—H···π interaction between the 2-methoxyphenyl rings [C3—H3···Cg1 (C2 → C7)] which is responsible for their edge-to-face orientation (Fig. 2).

Related literature top

For the biological activity of related compounds, see: Akgul & Anil (2003); Aslam et al. (2006); Galal et al. (2009); Khan et al. (2005); Soekamto et al. (2003). For the synthesis, see: Takeda et al. (2007).

Experimental top

2-(2'-methoxyphenyl]-benzo[b]furan was synthesized by the method described by Takeda (Takeda et al., 2007). Crystals were prepared by slow evaporation from acetonitrile.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. View of (I) with displacement ellipsoids shown at the 50% probability level.
	Fig. 2. Projection along the b axis with highlighted face-to-edge CH-π interactions between methoxyphenyl rings.

2-(2-Methoxyphenyl)-1-benzofuran top

Crystal data top

C₁₅H₁₂O₂	F(000) = 472
M_r = 224.25	D_x = 1.323 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: P 2ab 2ac	Cell parameters from 7843 reflections
a = 6.9419 (1) Å	θ = 3.1–66.9°
b = 11.4409 (2) Å	µ = 0.70 mm⁻¹
c = 14.1703 (3) Å	T = 120 K
V = 1125.43 (3) Å³	Plate, colourless
Z = 4	0.27 × 0.25 × 0.12 mm

Data collection top

Oxford Diffraction Xcalibur Atlas Gemini ultra diffractometer	2006 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	1955 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.050
Detector resolution: 10.3748 pixels mm^-1	θ_max = 67.1°, θ_min = 5.0°
Rotation method data acquisition using ω scans	h = −8→7
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −13→13
T_min = 0.683, T_max = 1.000	l = −16→14
11347 measured reflections

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)] = 0.033	H-atom parameters constrained
wR(F²) = 0.088	w = 1/[σ²(F_o²) + (0.0543P)² + 0.153P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max < 0.001
2006 reflections	Δρ_max = 0.20 e Å⁻³
155 parameters	Δρ_min = −0.14 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 822 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.2 (2)

Crystal data top

C₁₅H₁₂O₂	V = 1125.43 (3) Å³
M_r = 224.25	Z = 4
Orthorhombic, P2₁2₁2₁	Cu Kα radiation
a = 6.9419 (1) Å	µ = 0.70 mm⁻¹
b = 11.4409 (2) Å	T = 120 K
c = 14.1703 (3) Å	0.27 × 0.25 × 0.12 mm

Data collection top

Oxford Diffraction Xcalibur Atlas Gemini ultra diffractometer	2006 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	1955 reflections with I > 2σ(I)
T_min = 0.683, T_max = 1.000	R_int = 0.050
11347 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	H-atom parameters constrained
wR(F²) = 0.088	Δρ_max = 0.20 e Å⁻³
S = 1.09	Δρ_min = −0.14 e Å⁻³
2006 reflections	Absolute structure: Flack (1983), 822 Friedel pairs
155 parameters	Absolute structure parameter: −0.2 (2)
0 restraints

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. The hydrogen atoms were localized from the difference Fourier map. Despite of that,all hydrogen atoms connected to C were constrained to ideal positions. The isotropic temperature parameters of hydrogen atoms were calculated as 1.2*U_eq of the parent atom.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	1.06771 (15)	0.13587 (9)	0.33592 (7)	0.0323 (3)
O2	0.61359 (14)	0.36286 (9)	0.28934 (7)	0.0293 (3)
C2	1.0779 (2)	0.24444 (13)	0.37522 (10)	0.0282 (3)
C11	0.4903 (2)	0.32298 (13)	0.22083 (10)	0.0281 (3)
C6	0.9320 (2)	0.43475 (13)	0.38967 (10)	0.0301 (3)
H6	0.8355	0.4875	0.3737	0.036*
C7	0.9277 (2)	0.32219 (13)	0.35139 (10)	0.0275 (3)
C3	1.2221 (2)	0.27897 (14)	0.43667 (11)	0.0319 (3)
H3	1.3202	0.2272	0.4525	0.038*
C15	0.4610 (2)	0.17104 (13)	0.10446 (11)	0.0322 (3)
H15	0.5069	0.1044	0.0743	0.039*
C9	0.7486 (2)	0.20323 (12)	0.22207 (11)	0.0295 (3)
H9	0.8343	0.1430	0.2087	0.035*
C14	0.2874 (2)	0.22039 (14)	0.07865 (11)	0.0344 (4)
H14	0.2165	0.1869	0.0300	0.041*
C5	1.0769 (2)	0.46960 (13)	0.45085 (11)	0.0333 (3)
H5	1.0774	0.5449	0.4755	0.040*
C10	0.5664 (2)	0.22374 (13)	0.17718 (10)	0.0283 (3)
C8	0.7723 (2)	0.28854 (12)	0.28798 (10)	0.0268 (3)
C13	0.2159 (2)	0.31977 (14)	0.12430 (11)	0.0346 (4)
H13	0.0980	0.3505	0.1055	0.041*
C12	0.3160 (2)	0.37352 (14)	0.19675 (11)	0.0333 (3)
H12	0.2690	0.4395	0.2274	0.040*
C1	1.2147 (3)	0.05403 (14)	0.36035 (12)	0.0382 (4)
H1A	1.3373	0.0828	0.3394	0.046*
H1B	1.1884	−0.0196	0.3305	0.046*
H1C	1.2171	0.0438	0.4276	0.046*
C4	1.2206 (2)	0.39125 (14)	0.47490 (11)	0.0352 (4)
H4	1.3168	0.4136	0.5168	0.042*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0364 (5)	0.0258 (5)	0.0348 (5)	0.0044 (5)	−0.0035 (5)	−0.0030 (4)
O2	0.0288 (5)	0.0280 (5)	0.0311 (5)	0.0011 (4)	0.0007 (4)	−0.0013 (4)
C2	0.0321 (7)	0.0253 (7)	0.0272 (7)	−0.0002 (6)	0.0043 (6)	0.0028 (5)
C11	0.0276 (6)	0.0282 (7)	0.0284 (7)	−0.0049 (6)	0.0025 (6)	0.0041 (6)
C6	0.0328 (8)	0.0259 (7)	0.0317 (7)	0.0009 (6)	0.0005 (6)	0.0025 (6)
C7	0.0300 (7)	0.0253 (7)	0.0271 (7)	−0.0013 (6)	0.0031 (6)	0.0029 (6)
C3	0.0322 (7)	0.0303 (7)	0.0331 (8)	0.0005 (7)	−0.0021 (6)	0.0049 (6)
C15	0.0370 (8)	0.0273 (7)	0.0324 (7)	−0.0031 (6)	−0.0008 (6)	0.0006 (6)
C9	0.0320 (7)	0.0251 (7)	0.0314 (8)	0.0011 (6)	0.0007 (6)	−0.0008 (6)
C14	0.0351 (8)	0.0332 (8)	0.0349 (8)	−0.0076 (7)	−0.0039 (7)	0.0039 (6)
C5	0.0388 (8)	0.0257 (7)	0.0352 (8)	−0.0034 (7)	−0.0023 (7)	−0.0010 (6)
C10	0.0307 (7)	0.0251 (7)	0.0291 (7)	−0.0032 (6)	0.0026 (6)	0.0033 (6)
C8	0.0279 (6)	0.0235 (7)	0.0289 (7)	0.0008 (6)	0.0030 (6)	0.0033 (6)
C13	0.0276 (7)	0.0372 (8)	0.0389 (8)	−0.0024 (7)	−0.0013 (6)	0.0072 (7)
C12	0.0318 (7)	0.0309 (8)	0.0373 (8)	0.0014 (7)	0.0046 (6)	0.0029 (6)
C1	0.0394 (8)	0.0316 (8)	0.0437 (9)	0.0092 (7)	−0.0027 (7)	−0.0036 (7)
C4	0.0382 (8)	0.0326 (8)	0.0348 (8)	−0.0048 (7)	−0.0059 (7)	0.0015 (6)

Geometric parameters (Å, º) top

O1—C2	1.3630 (18)	C15—H15	0.9300
O1—C1	1.4273 (18)	C9—C8	1.361 (2)
O2—C11	1.3723 (18)	C9—C10	1.435 (2)
O2—C8	1.3921 (17)	C9—H9	0.9300
C2—C3	1.384 (2)	C14—C13	1.399 (2)
C2—C7	1.411 (2)	C14—H14	0.9300
C11—C12	1.384 (2)	C5—C4	1.384 (2)
C11—C10	1.397 (2)	C5—H5	0.9300
C6—C5	1.386 (2)	C13—C12	1.384 (2)
C6—C7	1.398 (2)	C13—H13	0.9300
C6—H6	0.9300	C12—H12	0.9300
C7—C8	1.456 (2)	C1—H1A	0.9600
C3—C4	1.394 (2)	C1—H1B	0.9600
C3—H3	0.9300	C1—H1C	0.9600
C15—C14	1.380 (2)	C4—H4	0.9300
C15—C10	1.400 (2)

C2—O1—C1	117.50 (12)	C13—C14—H14	119.3
C11—O2—C8	106.31 (11)	C4—C5—C6	119.38 (14)
O1—C2—C3	123.68 (14)	C4—C5—H5	120.3
O1—C2—C7	116.00 (14)	C6—C5—H5	120.3
C3—C2—C7	120.31 (13)	C11—C10—C15	118.58 (14)
O2—C11—C12	125.51 (14)	C11—C10—C9	105.67 (13)
O2—C11—C10	110.34 (13)	C15—C10—C9	135.74 (15)
C12—C11—C10	124.14 (14)	C9—C8—O2	110.60 (12)
C5—C6—C7	121.56 (14)	C9—C8—C7	134.67 (14)
C5—C6—H6	119.2	O2—C8—C7	114.61 (11)
C7—C6—H6	119.2	C12—C13—C14	121.74 (15)
C6—C7—C2	118.17 (14)	C12—C13—H13	119.1
C6—C7—C8	119.94 (13)	C14—C13—H13	119.1
C2—C7—C8	121.89 (13)	C11—C12—C13	115.87 (15)
C2—C3—C4	120.13 (15)	C11—C12—H12	122.1
C2—C3—H3	119.9	C13—C12—H12	122.1
C4—C3—H3	119.9	O1—C1—H1A	109.5
C14—C15—C10	118.36 (15)	O1—C1—H1B	109.5
C14—C15—H15	120.8	H1A—C1—H1B	109.5
C10—C15—H15	120.8	O1—C1—H1C	109.5
C8—C9—C10	107.07 (13)	H1A—C1—H1C	109.5
C8—C9—H9	126.5	H1B—C1—H1C	109.5
C10—C9—H9	126.5	C5—C4—C3	120.42 (15)
C15—C14—C13	121.31 (15)	C5—C4—H4	119.8
C15—C14—H14	119.3	C3—C4—H4	119.8

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C2–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O2ⁱ	0.96	2.57	3.272 (2)	131
C3—H3···Cg1ⁱⁱ	0.93	2.78	3.604 (2)	149

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₂O₂
M_r	224.25
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	120
a, b, c (Å)	6.9419 (1), 11.4409 (2), 14.1703 (3)
V (Å³)	1125.43 (3)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.70
Crystal size (mm)	0.27 × 0.25 × 0.12

Data collection
Diffractometer	Oxford Diffraction Xcalibur Atlas Gemini ultra diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.683, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	11347, 2006, 1955
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.088, 1.09
No. of reflections	2006
No. of parameters	155
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.14
Absolute structure	Flack (1983), 822 Friedel pairs
Absolute structure parameter	−0.2 (2)

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C2–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O2ⁱ	0.96	2.57	3.272 (2)	131
C3—H3···Cg1ⁱⁱ	0.93	2.78	3.604 (2)	149

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

Acknowledgements

This work was supported by the Institutional research plan No. AVOZ10100521 of the Institute of Physics, the project Praemium Academiae of the Academy of Sciences of the Czech Republic and the Czech Ministry of Education, Youth and Sports, project MSM 4977751303.

References

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