Methyl 5-(1-benzo­furan-2-yl)isoxazole-3-carboxyl­ate

El-Hiti, G.A.; Abdel-Wahab, B.F.; Alotaibi, M.H.; Hegazy, A.S.; Kariuki, B.M.

doi:10.1107/S241431461701820X

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 12| December 2017| x171820

https://doi.org/10.1107/S241431461701820X

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Methyl 5-(1-benzofuran-2-yl)isoxazole-3-carboxylate

Gamal A. El-Hiti,^a ^* Bakr F. Abdel-Wahab,^b,^c Mohammad Hayal Alotaibi,^d Amany S. Hegazy ^e and Benson M. Kariuki ^e ‡

^aCornea Research Chair, Department of Optometry, College of Applied Medical Sciences, King Saud University, PO Box 10219, Riyadh 11433, Saudi Arabia, ^bDepartment of Chemistry, College of Science and Humanities, Shaqra University, Duwadimi, Saudi Arabia, ^cApplied Organic Chemistry Department, National Research Centre, Dokki, Giza, Egypt, ^dNational Center for Petrochemicals Technology, King Abdulaziz City for Science and Technology, PO Box 6086, Riyadh 11442, Saudi Arabia, and ^eSchool of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, UK
^*Correspondence e-mail: gelhiti@ksu.edu.sa

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 15 December 2017; accepted 19 December 2017; online 22 December 2017)

The title compound, C₁₃H₉NO₄, is almost planar (r.m.s. deviation = 0.071 Å). In the crystal, weak C—H⋯O and C—H⋯N interactions connect the molecules into ribbons propagating parallel to the a-axis direction.

Keywords: crystal structure; benzofuran; synthesis.

CCDC reference: 1812524

Structure description

Compounds containing a benzofuran ring system show interesting pharmaceutical applications (Khanam & Shamsuzzaman, 2015 ; Dawood, 2013 ). As part of our studies in this area, we now describe the crystal structure of the title compound.

Apart from the methyl hydrogen atoms, the molecule (Fig. 1) is almost planar [dihedral angle between the ring systems = 0.27 (9)°; r.m.s. deviation for the non-hydrogen atoms = 0.071 Å]. In the crystal, weak C—H⋯O and extremely weak C—H⋯N interactions form ribbons running parallel to [100] (Table 1, Fig. 2) with adjacent molecules in the chain related by a-glide symmetry.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O3ⁱ	0.93	2.47	3.248 (3)	142
C10—H10⋯N1ⁱ	0.93	2.69	3.600 (2)	165
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ .

Figure 1
The molecular structure showing 50% displacement ellipsoids.

Figure 2
Intermolecular interactions forming a ribbon along the a-axis.

Synthesis and crystallization

The title compound was synthesized based on a literature procedure (Siddiqui et al., 2013 ) and recrystallized from dimethylformamide solution to yield colourless block-shaped crystals.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₃H₉NO₄
M_r	243.21
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	11.5170 (6), 8.7431 (4), 22.2595 (13)
V (Å³)	2241.4 (2)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	0.11
Crystal size (mm)	0.29 × 0.24 × 0.20

Data collection
Diffractometer	Agilent SuperNova, Dual, Cu at zero, Atlas
Absorption correction	Gaussian (CrysAlis PRO; Agilent, 2014 )
T_min, T_max	0.993, 0.995
No. of measured, independent and observed [I > 2σ(I)] reflections	7841, 2754, 1729
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.693

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.128, 1.04
No. of reflections	2754
No. of parameters	164
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.18
Computer programs: CrysAlis PRO (Agilent, 2014), SHELXS2013 (Sheldrick, 2008 ), SHELXL2013 (Sheldrick, 2015 ), ORTEP-3 for Windows and WinGX (Farrugia, 2012 ) and CHEMDRAW Ultra (Cambridge Soft, 2001 ).

Structural data

CCDC reference: 1812524

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S241431461701820X/hb4192sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S241431461701820X/hb4192Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S241431461701820X/hb4192Isup3.cml

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and CHEMDRAW Ultra (Cambridge Soft, 2001).

Methyl 5-(1-benzofuran-2-yl)isoxazole-3-carboxylate top

Crystal data top

C₁₃H₉NO₄	D_x = 1.441 Mg m⁻³
M_r = 243.21	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 2289 reflections
a = 11.5170 (6) Å	θ = 4.7–27.2°
b = 8.7431 (4) Å	µ = 0.11 mm⁻¹
c = 22.2595 (13) Å	T = 296 K
V = 2241.4 (2) Å³	Block, colourless
Z = 8	0.29 × 0.24 × 0.20 mm
F(000) = 1008

Data collection top

Agilent SuperNova, Dual, Cu at zero, Atlas diffractometer	1729 reflections with I > 2σ(I)
ω scans	R_int = 0.023
Absorption correction: gaussian (CrysAlis PRO; Agilent, 2014)	θ_max = 29.5°, θ_min = 3.5°
T_min = 0.993, T_max = 0.995	h = −15→11
7841 measured reflections	k = −8→11
2754 independent reflections	l = −30→30

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.051	H-atom parameters constrained
wR(F²) = 0.128	w = 1/[σ²(F_o²) + (0.0435P)² + 0.7049P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2754 reflections	Δρ_max = 0.16 e Å⁻³
164 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. All hydrogen atoms were placed in calculated positions and refined using a riding model. Methyl C—H bonds were fixed at 0.96 Å, with displacement parameters 1.5 times U_eq(C), and were allowed to spin about the C—C bond. Aromatic C—H distances were set to 0.93 Å and their U(iso) set to 1.2 times the U_eq for the atoms to which they are bonded.

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

	x	y	z	U_iso*/U_eq
C1	0.67167 (18)	0.3721 (2)	0.65576 (8)	0.0537 (5)
C2	0.7252 (2)	0.2758 (3)	0.69597 (10)	0.0708 (6)
H2	0.8055	0.2638	0.6967	0.085*
C3	0.6540 (3)	0.1981 (3)	0.73512 (10)	0.0758 (7)
H3	0.6866	0.1318	0.7631	0.091*
C4	0.5339 (2)	0.2169 (3)	0.73359 (11)	0.0730 (6)
H4	0.4880	0.1625	0.7605	0.088*
C5	0.4817 (2)	0.3140 (2)	0.69324 (10)	0.0655 (6)
H5	0.4015	0.3260	0.6927	0.079*
C6	0.55252 (17)	0.3945 (2)	0.65298 (9)	0.0521 (5)
C7	0.53436 (16)	0.5028 (2)	0.60614 (9)	0.0527 (5)
H7	0.4634	0.5416	0.5932	0.063*
C8	0.63964 (16)	0.5379 (2)	0.58428 (8)	0.0490 (4)
C9	0.67308 (15)	0.6425 (2)	0.53750 (8)	0.0480 (4)
C10	0.61160 (16)	0.7336 (2)	0.50057 (8)	0.0501 (4)
H10	0.5314	0.7451	0.4988	0.060*
C11	0.69573 (15)	0.8071 (2)	0.46541 (8)	0.0475 (4)
C12	0.67921 (17)	0.9195 (2)	0.41622 (9)	0.0527 (5)
C13	0.5415 (2)	1.0774 (3)	0.36919 (10)	0.0745 (6)
H13A	0.5791	1.1724	0.3785	0.112*
H13B	0.4589	1.0925	0.3682	0.112*
H13C	0.5674	1.0416	0.3307	0.112*
N1	0.80140 (13)	0.76549 (19)	0.47946 (8)	0.0568 (4)
O1	0.72689 (11)	0.45958 (15)	0.61324 (6)	0.0565 (4)
O2	0.78819 (10)	0.65920 (15)	0.52603 (6)	0.0570 (4)
O3	0.75434 (14)	0.96214 (19)	0.38300 (7)	0.0768 (5)
O4	0.56996 (11)	0.96551 (16)	0.41459 (6)	0.0610 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0607 (12)	0.0534 (11)	0.0471 (10)	0.0046 (9)	−0.0011 (9)	−0.0067 (9)
C2	0.0727 (15)	0.0787 (15)	0.0612 (13)	0.0129 (12)	−0.0069 (11)	0.0009 (12)
C3	0.105 (2)	0.0684 (14)	0.0541 (12)	0.0145 (14)	−0.0020 (13)	0.0021 (11)
C4	0.0961 (19)	0.0607 (13)	0.0621 (13)	−0.0018 (13)	0.0144 (13)	−0.0011 (11)
C5	0.0709 (14)	0.0580 (11)	0.0675 (13)	−0.0009 (11)	0.0119 (11)	−0.0039 (11)
C6	0.0546 (12)	0.0479 (10)	0.0538 (11)	0.0014 (9)	0.0025 (9)	−0.0097 (9)
C7	0.0442 (10)	0.0515 (10)	0.0625 (12)	0.0028 (8)	−0.0015 (9)	−0.0038 (9)
C8	0.0461 (10)	0.0496 (10)	0.0512 (10)	0.0041 (8)	−0.0043 (8)	−0.0075 (9)
C9	0.0387 (9)	0.0517 (10)	0.0537 (10)	−0.0005 (8)	0.0020 (8)	−0.0108 (9)
C10	0.0369 (9)	0.0585 (11)	0.0548 (10)	0.0005 (8)	−0.0005 (8)	−0.0049 (9)
C11	0.0399 (10)	0.0503 (10)	0.0522 (10)	0.0007 (8)	0.0006 (8)	−0.0104 (9)
C12	0.0486 (11)	0.0568 (11)	0.0526 (11)	−0.0025 (9)	0.0015 (9)	−0.0069 (9)
C13	0.0792 (16)	0.0744 (14)	0.0698 (14)	0.0081 (12)	−0.0176 (12)	0.0078 (12)
N1	0.0444 (9)	0.0608 (10)	0.0651 (10)	0.0012 (8)	0.0038 (8)	0.0006 (9)
O1	0.0463 (8)	0.0653 (8)	0.0579 (8)	0.0054 (6)	−0.0023 (6)	0.0010 (7)
O2	0.0407 (7)	0.0623 (8)	0.0680 (9)	0.0049 (6)	0.0003 (6)	0.0019 (7)
O3	0.0590 (9)	0.0931 (12)	0.0782 (10)	−0.0027 (8)	0.0141 (8)	0.0173 (9)
O4	0.0492 (8)	0.0714 (9)	0.0625 (8)	0.0041 (7)	−0.0041 (6)	0.0062 (7)

Geometric parameters (Å, º) top

C1—O1	1.373 (2)	C8—C9	1.438 (3)
C1—C2	1.375 (3)	C9—C10	1.346 (3)
C1—C6	1.388 (3)	C9—O2	1.358 (2)
C2—C3	1.377 (3)	C10—C11	1.402 (3)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.393 (4)	C11—N1	1.308 (2)
C3—H3	0.9300	C11—C12	1.483 (3)
C4—C5	1.375 (3)	C12—O3	1.198 (2)
C4—H4	0.9300	C12—O4	1.322 (2)
C5—C6	1.401 (3)	C13—O4	1.444 (2)
C5—H5	0.9300	C13—H13A	0.9600
C6—C7	1.424 (3)	C13—H13B	0.9600
C7—C8	1.342 (3)	C13—H13C	0.9600
C7—H7	0.9300	N1—O2	1.401 (2)
C8—O1	1.376 (2)

O1—C1—C2	125.59 (19)	O1—C8—C9	117.38 (16)
O1—C1—C6	110.40 (16)	C10—C9—O2	109.58 (16)
C2—C1—C6	124.0 (2)	C10—C9—C8	132.65 (17)
C1—C2—C3	116.5 (2)	O2—C9—C8	117.77 (16)
C1—C2—H2	121.7	C9—C10—C11	104.40 (16)
C3—C2—H2	121.7	C9—C10—H10	127.8
C2—C3—C4	121.2 (2)	C11—C10—H10	127.8
C2—C3—H3	119.4	N1—C11—C10	112.46 (17)
C4—C3—H3	119.4	N1—C11—C12	118.69 (17)
C5—C4—C3	121.6 (2)	C10—C11—C12	128.85 (17)
C5—C4—H4	119.2	O3—C12—O4	125.17 (19)
C3—C4—H4	119.2	O3—C12—C11	124.70 (19)
C4—C5—C6	118.3 (2)	O4—C12—C11	110.13 (16)
C4—C5—H5	120.9	O4—C13—H13A	109.5
C6—C5—H5	120.9	O4—C13—H13B	109.5
C1—C6—C5	118.43 (19)	H13A—C13—H13B	109.5
C1—C6—C7	105.78 (17)	O4—C13—H13C	109.5
C5—C6—C7	135.8 (2)	H13A—C13—H13C	109.5
C8—C7—C6	106.55 (17)	H13B—C13—H13C	109.5
C8—C7—H7	126.7	C11—N1—O2	105.10 (14)
C6—C7—H7	126.7	C1—O1—C8	105.19 (14)
C7—C8—O1	112.08 (17)	C9—O2—N1	108.46 (13)
C7—C8—C9	130.53 (17)	C12—O4—C13	116.21 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O3ⁱ	0.93	2.47	3.248 (3)	142
C10—H10···N1ⁱ	0.93	2.69	3.600 (2)	165

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

Footnotes

‡Additional correspondence author, e-mail: kariukib@cf.ac.uk.

Funding information

The project was supported by King Saud University, Deanship of Scientific Research, Research Chairs.

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