3-(5-Nitro-2-fur­yl)-1-phenyl­prop-2-yn-1-one

Fun, H.-K.; Quah, C.K.; Nithinchandra; Kalluraya, B.

doi:10.1107/S1600536810043850

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Pages o3031-o3032

https://doi.org/10.1107/S1600536810043850

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3-(5-Nitro-2-furyl)-1-phenylprop-2-yn-1-one

Hoong-Kun Fun,^a ^*‡ Ching Kheng Quah,^a § Nithinchandra ^b and Balakrishna Kalluraya ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India
^*Correspondence e-mail: hkfun@usm.my

(Received 19 October 2010; accepted 27 October 2010; online 31 October 2010)

In the title compound, C₁₃H₇NO₄, the 2-furyl ring is essentially planar, with a maximum deviation of 0.004 (1) Å. It is inclined at an angle of 11.69 (4)° to the benzene ring. The nitro group is slightly twisted out of the plane of the 2-furyl ring, with a dihedral angle of 5.72 (8)°. There is a short O⋯C contact of 2.8562 (8) Å (symmetry code: −x, −y, 2 − z). In the crystal packing, molecules are linked via a pair of intermolecular C—H⋯O hydrogen bonds, giving rise to an R₂²(10) ring motif. Molecules are further linked into two-dimensional networks parallel to [100] via other intermolecular C—H⋯O hydrogen bonds. The crystal structure is consolidated by C—H⋯π interactions.

Related literature

For general background to the biological activity of nitrofurans, see: Holla et al. (1986 , 1987 , 1992 ). For the preparation of the title compound, see: Rai et al. (2008 ). For bond-length data, see: Allen et al. (1987 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₃H₇NO₄
M_r = 241.20
Monoclinic, P 2₁ /c
a = 10.4685 (2) Å
b = 7.3006 (1) Å
c = 15.2642 (2) Å
β = 110.867 (1)°
V = 1090.07 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 100 K
0.47 × 0.38 × 0.28 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.950, T_max = 0.970
40673 measured reflections
5796 independent reflections
4934 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.119
S = 1.04
5796 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.59 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the phenyl (C8–C12) ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O2ⁱ	0.93	2.44	3.3548 (9)	170
C11—H11⋯O4ⁱⁱ	0.93	2.40	3.2487 (9)	152
C3—H3⋯Cg1ⁱⁱⁱ	0.93	2.86	3.6284 (7)	141
Symmetry codes: (i) -x-1, -y+1, -z+2; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810043850/fj2357sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810043850/fj2357Isup2.hkl

checkCIF report

Comment top

Nitrofurans are class of synthetic compounds characterized by the presence of 5-nitro-2-furyl group. The presence of nitro group in the position-5 of the molecule conferred antibacterial activity (Holla et al., 1986). A number of nitrofurans have attained commercial utility as antibacterial agents in humans and in veterinary medicine because of their broad spectrum of activity (Holla et al., 1992; Holla et al., 1987). 1-Aryl-3-(5-nitro-2-furyl)-2-propyn-1-ones were prepared by the hydrobromination of 2,3-dibromo-1-aryl-3-(5-nitro-2-furyl)-2-propan-1-ones in the presence of triethylamine in benzene medium. The dibromopropanones were in turn obtained by the bromination of 1-aryl-3-(5-nitro-2-furyl)-2-propen-1-ones. Acid catalysed condensation of acetophenones with 5- nitrofuraldiacetate in acetic acid yielded the required 1-aryl-3-(5-nitro-2-furyl)-2-propen-1-ones called chalcones (Rai et al., 2008).

In the title molecule (Fig. 1), the 2-furyl (O1/C1–C4) ring is essentially planar (maximum deviation = 0.004 (1) Å for atoms O1) and is inclined at an angle of 11.69 (4)° with the phenyl ring (C11–C16), which indicates they are nearly parallel to each other. The nitro group (N1/O1/O2) is slightly twisted away from the attached 2-furyl ring [dihedral angle = 5.72 (8)]. There is a short O4···C1 contact (symmetry code : -x, -y, 2 - z) with distance = 2.8562 (8) Å which is shorter than the sum of van der Waals radii of the O and C atoms. Bond lengths (Allen et al., 1987) and angles are within normal ranges.

In the crystal packing (Fig. 2), the molecules are linked via a pair of intermolecular C2—H2···O2 hydrogen bonds, displaying R₂²(10) ring motifs (Bernstein et al., 1995). The molecules are further linked into two-dimensional networks parallel to (100) via intermolecular C11—H11···O4 hydrogen bonds. The crystal structure is further consilidated by C3—H3···Cg1 (Table 1), where Cg1 is the centroid of C8–C13 phenyl ring.

Related literature top

For general background to the biological activity of nitrofurans, see: Holla et al. (1986, 1987, 1992). For the preparation of the title compound, see: Rai et al. (2008). For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

To a stirred solution of 2,3-dibromo-3-(5-nitro-2-furyl)-1-phenylpropan-1-one (0.01 mol) in dry benzene (100 ml), a solution of triethylamine (0.04 mol) in dry benzene (30 ml) was added. The reaction mixture was stirred at room temperature for 24 h. The resulting mass of triethylamine hydrobromide was removed by filtration and the filtrate was concentrated by distilling the benzene under reduced pressure. The concentrated solution was cooled to room temperature. The product formed was collected by filtration and washed with ethanol. It was then recrystallized from ethanol. Crystals suitable for X-ray analysis were obtained from 1:2 mixtures of DMF and ethanol by slow evaporation.

Structure description top

For general background to the biological activity of nitrofurans, see: Holla et al. (1986, 1987, 1992). For the preparation of the title compound, see: Rai et al. (2008). For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound showing 50% probability displacement ellipsoids for non-H atoms and the atom-numbering scheme.
	Fig. 2. The crystal structure of the title compound, viewed along the a axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.

3-(5-Nitro-2-furyl)-1-phenylprop-2-yn-1-one top

Crystal data top

C₁₃H₇NO₄	F(000) = 496
M_r = 241.20	D_x = 1.470 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9876 reflections
a = 10.4685 (2) Å	θ = 2.8–37.6°
b = 7.3006 (1) Å	µ = 0.11 mm⁻¹
c = 15.2642 (2) Å	T = 100 K
β = 110.867 (1)°	Block, brown
V = 1090.07 (3) Å³	0.47 × 0.38 × 0.28 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5796 independent reflections
Radiation source: fine-focus sealed tube	4934 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
φ and ω scans	θ_max = 37.7°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −17→17
T_min = 0.950, T_max = 0.970	k = −12→12
40673 measured reflections	l = −25→26

Refinement top

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0678P)² + 0.1893P] where P = (F_o² + 2F_c²)/3
5796 reflections	(Δ/σ)_max = 0.002
163 parameters	Δρ_max = 0.59 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₁₃H₇NO₄	V = 1090.07 (3) Å³
M_r = 241.20	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.4685 (2) Å	µ = 0.11 mm⁻¹
b = 7.3006 (1) Å	T = 100 K
c = 15.2642 (2) Å	0.47 × 0.38 × 0.28 mm
β = 110.867 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5796 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4934 reflections with I > 2σ(I)
T_min = 0.950, T_max = 0.970	R_int = 0.030
40673 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 1.04	Δρ_max = 0.59 e Å⁻³
5796 reflections	Δρ_min = −0.33 e Å⁻³
163 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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. 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 > 2sigma(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	−0.11630 (5)	0.27415 (7)	1.04906 (3)	0.01471 (9)
O2	−0.39290 (6)	0.35131 (8)	1.11730 (4)	0.02350 (11)
O3	−0.19217 (6)	0.23310 (8)	1.19322 (4)	0.02173 (10)
O4	0.31281 (5)	0.03921 (7)	0.98678 (3)	0.01702 (9)
N1	−0.27662 (6)	0.30540 (8)	1.12394 (4)	0.01630 (10)
C1	−0.23941 (6)	0.33853 (8)	1.04384 (4)	0.01429 (10)
C2	−0.31207 (6)	0.41459 (9)	0.95952 (5)	0.01643 (11)
H2	−0.3984	0.4675	0.9412	0.020*
C3	−0.22679 (6)	0.39527 (9)	0.90560 (5)	0.01704 (11)
H3	−0.2463	0.4335	0.8441	0.020*
C4	−0.11011 (6)	0.30936 (9)	0.96198 (4)	0.01464 (10)
C5	0.00843 (6)	0.25151 (9)	0.94661 (5)	0.01623 (11)
C6	0.10953 (6)	0.20010 (9)	0.93282 (4)	0.01633 (11)
C7	0.23677 (6)	0.13782 (8)	0.92494 (4)	0.01320 (10)
C8	0.27014 (6)	0.19941 (8)	0.84344 (4)	0.01292 (10)
C9	0.17614 (7)	0.29769 (9)	0.76987 (4)	0.01676 (11)
H9	0.0897	0.3240	0.7707	0.020*
C10	0.21317 (8)	0.35576 (10)	0.69539 (5)	0.02011 (12)
H10	0.1514	0.4214	0.6463	0.024*
C11	0.34271 (8)	0.31575 (10)	0.69438 (5)	0.02020 (12)
H11	0.3673	0.3559	0.6448	0.024*
C12	0.43585 (7)	0.21588 (10)	0.76724 (5)	0.01871 (11)
H12	0.5219	0.1886	0.7658	0.022*
C13	0.39983 (6)	0.15728 (9)	0.84181 (4)	0.01523 (10)
H13	0.4615	0.0904	0.8904	0.018*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.01147 (17)	0.01760 (19)	0.01634 (19)	0.00183 (14)	0.00653 (14)	0.00090 (15)
O2	0.0173 (2)	0.0286 (3)	0.0299 (3)	0.00376 (18)	0.0150 (2)	−0.0001 (2)
O3	0.0219 (2)	0.0261 (2)	0.0180 (2)	0.00245 (18)	0.00804 (18)	0.00227 (18)
O4	0.0181 (2)	0.0185 (2)	0.01441 (18)	0.00230 (15)	0.00568 (15)	0.00193 (15)
N1	0.0158 (2)	0.0164 (2)	0.0192 (2)	0.00019 (17)	0.00932 (18)	−0.00110 (17)
C1	0.0117 (2)	0.0154 (2)	0.0176 (2)	0.00109 (17)	0.00733 (18)	−0.00024 (18)
C2	0.0131 (2)	0.0173 (2)	0.0191 (2)	0.00249 (18)	0.00597 (19)	0.00072 (19)
C3	0.0155 (2)	0.0189 (3)	0.0172 (2)	0.00230 (19)	0.00642 (19)	0.00149 (19)
C4	0.0132 (2)	0.0159 (2)	0.0166 (2)	0.00058 (17)	0.00742 (18)	−0.00012 (18)
C5	0.0143 (2)	0.0174 (2)	0.0190 (2)	−0.00023 (18)	0.0085 (2)	−0.00129 (19)
C6	0.0148 (2)	0.0186 (3)	0.0177 (2)	0.00069 (19)	0.00826 (19)	−0.00003 (19)
C7	0.0124 (2)	0.0142 (2)	0.0139 (2)	−0.00032 (16)	0.00575 (17)	−0.00142 (17)
C8	0.0122 (2)	0.0142 (2)	0.0128 (2)	0.00024 (16)	0.00488 (17)	0.00001 (16)
C9	0.0150 (2)	0.0180 (2)	0.0157 (2)	0.00193 (19)	0.00354 (19)	0.00166 (19)
C10	0.0241 (3)	0.0193 (3)	0.0146 (2)	−0.0002 (2)	0.0040 (2)	0.0030 (2)
C11	0.0263 (3)	0.0213 (3)	0.0146 (2)	−0.0062 (2)	0.0092 (2)	−0.0006 (2)
C12	0.0179 (3)	0.0233 (3)	0.0179 (2)	−0.0032 (2)	0.0100 (2)	−0.0016 (2)
C13	0.0126 (2)	0.0190 (2)	0.0150 (2)	0.00056 (18)	0.00601 (18)	0.00020 (18)

Geometric parameters (Å, º) top

O1—C1	1.3472 (7)	C6—C7	1.4525 (8)
O1—C4	1.3779 (8)	C7—C8	1.4770 (8)
O2—N1	1.2315 (7)	C8—C9	1.3990 (8)
O3—N1	1.2298 (8)	C8—C13	1.4010 (8)
O4—C7	1.2278 (8)	C9—C10	1.3915 (9)
N1—C1	1.4298 (8)	C9—H9	0.9300
C1—C2	1.3586 (9)	C10—C11	1.3927 (11)
C2—C3	1.4205 (9)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.3953 (10)
C3—C4	1.3701 (9)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.3880 (9)
C4—C5	1.4073 (8)	C12—H12	0.9300
C5—C6	1.2100 (8)	C13—H13	0.9300

C1—O1—C4	104.51 (5)	C6—C7—C8	118.26 (5)
O3—N1—O2	125.05 (6)	C9—C8—C13	120.49 (5)
O3—N1—C1	118.47 (5)	C9—C8—C7	121.50 (5)
O2—N1—C1	116.48 (6)	C13—C8—C7	118.01 (5)
O1—C1—C2	113.56 (5)	C10—C9—C8	119.41 (6)
O1—C1—N1	115.88 (5)	C10—C9—H9	120.3
C2—C1—N1	130.40 (5)	C8—C9—H9	120.3
C1—C2—C3	104.66 (5)	C9—C10—C11	120.06 (6)
C1—C2—H2	127.7	C9—C10—H10	120.0
C3—C2—H2	127.7	C11—C10—H10	120.0
C4—C3—C2	106.57 (6)	C10—C11—C12	120.49 (6)
C4—C3—H3	126.7	C10—C11—H11	119.8
C2—C3—H3	126.7	C12—C11—H11	119.8
C3—C4—O1	110.71 (5)	C13—C12—C11	119.86 (6)
C3—C4—C5	132.41 (6)	C13—C12—H12	120.1
O1—C4—C5	116.88 (5)	C11—C12—H12	120.1
C6—C5—C4	179.25 (7)	C12—C13—C8	119.67 (6)
C5—C6—C7	175.08 (7)	C12—C13—H13	120.2
O4—C7—C6	118.85 (5)	C8—C13—H13	120.2
O4—C7—C8	122.88 (5)

C4—O1—C1—C2	−0.69 (7)	O4—C7—C8—C9	174.06 (6)
C4—O1—C1—N1	175.17 (5)	C6—C7—C8—C9	−7.19 (9)
O3—N1—C1—O1	4.75 (9)	O4—C7—C8—C13	−6.23 (9)
O2—N1—C1—O1	−174.73 (6)	C6—C7—C8—C13	172.52 (6)
O3—N1—C1—C2	179.76 (7)	C13—C8—C9—C10	−0.90 (10)
O2—N1—C1—C2	0.28 (11)	C7—C8—C9—C10	178.80 (6)
O1—C1—C2—C3	0.46 (8)	C8—C9—C10—C11	0.11 (10)
N1—C1—C2—C3	−174.65 (7)	C9—C10—C11—C12	0.64 (11)
C1—C2—C3—C4	−0.02 (7)	C10—C11—C12—C13	−0.61 (11)
C2—C3—C4—O1	−0.40 (7)	C11—C12—C13—C8	−0.18 (10)
C2—C3—C4—C5	178.65 (7)	C9—C8—C13—C12	0.93 (10)
C1—O1—C4—C3	0.65 (7)	C7—C8—C13—C12	−178.78 (6)
C1—O1—C4—C5	−178.56 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2ⁱ	0.93	2.44	3.3548 (9)	170
C11—H11···O4ⁱⁱ	0.93	2.40	3.2487 (9)	152
C3—H3···Cg1ⁱⁱⁱ	0.93	2.86	3.6284 (7)	141

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

Experimental details

Crystal data
Chemical formula	C₁₃H₇NO₄
M_r	241.20
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	10.4685 (2), 7.3006 (1), 15.2642 (2)
β (°)	110.867 (1)
V (Å³)	1090.07 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.47 × 0.38 × 0.28

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.950, 0.970
No. of measured, independent and observed [I > 2σ(I)] reflections	40673, 5796, 4934
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.860

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.119, 1.04
No. of reflections	5796
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.59, −0.33

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2ⁱ	0.9300	2.4400	3.3548 (9)	170.00
C11—H11···O4ⁱⁱ	0.9300	2.4000	3.2487 (9)	152.00
C3—H3···Cg1ⁱⁱⁱ	0.9300	2.8600	3.6284 (7)	141.00

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5525-2009.

Acknowledgements

The authors express their thanks to Universiti Sains Malysia (USM) for providing research facilities. HKF and CKQ thank USM for a Research University Grant (No. 1001/PFIZIK/811160). CKQ also thanks USM for the award of a USM fellowship.

References

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