(E)-3-(3,4-Dimethoxy­phen­yl)-1-(2-fur­yl)prop-2-en-1-one

Fun, H.-K.; Patil, P.S.; Jebas, S.R.; Dharmaprakash, S.M.

doi:10.1107/S1600536808020539

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Pages o1434-o1435

doi:10.1107/S1600536808020539

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(E)-3-(3,4-Dimethoxyphenyl)-1-(2-furyl)prop-2-en-1-one

Hoong-Kun Fun,^a ^* P. S. Patil,^b Samuel Robinson Jebas ^a ‡ and S. M. Dharmaprakash ^b

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

(Received 1 July 2008; accepted 3 July 2008; online 9 July 2008)

In the title molecule, C₁₅H₁₄O₄, the benzene and furyl rings are inclined to each other with a dihedral angle of 41.5 (1)°. An intramolecular C—H⋯O hydrogen-bond interaction generates an S(5) ring motif. In the crystal structure, molecules are stacked along the b axis and the crystal packing is stabilized by intermolecular C—H⋯O and C—H⋯π interactions. In addition, π–π stacking interactions with a centroid-to-centroid distance of 3.5855 (11) Å are observed.

Related literature

For related literature on the non-linear optical properties of chromophore derivatives, see: Agrinskaya et al. (1999 ). For other related literature, see: Chantrapromma et al. (2005 , 2006 ); Fun et al. (2006 ); Patil, Fun et al. (2007 ); Patil, Dharmaprakash et al. (2007 ); Patil et al. (2006 ). For bond-length data, see: Allen et al. (1987 ). For graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₅H₁₄O₄
M_r = 258.26
Monoclinic, C 2
a = 21.5582 (5) Å
b = 5.6105 (1) Å
c = 10.4622 (3) Å
β = 101.510 (2)°
V = 1239.98 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100.0 (1) K
0.42 × 0.05 × 0.04 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.947, T_max = 0.996
7017 measured reflections
1997 independent reflections
1707 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.104
S = 1.10
1997 reflections
174 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the ring C8–C13

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O2ⁱ	0.93	2.32	3.247 (3)	173
C3—H3A⋯O3ⁱⁱ	0.93	2.42	3.338 (3)	167
C7—H7A⋯O2	0.93	2.47	2.810 (3)	101
C14—H14B⋯Cg1ⁱⁱⁱ	0.96	2.66	3.431 (2)	137
Symmetry codes: (i) x, y+1, z; (ii) $[x+{\script{1\over 2}}, y-{\script{1\over 2}}, z+1]$ ; (iii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+2]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); 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, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808020539/lh2655sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808020539/lh2655Isup2.hkl

checkCIF report

Comment top

Among the many types of NLO chromophores developed so far, the dipolar push–pull molecules consisting of electron donor and acceptor groups inter-bridged by a π-segment have received the predominant attention (Agrinskaya et al., 1999). As a part of the investigation of nonlinear compounds (Chantrapromma et al., 2005, 2006; Fun et al., 2006; Patil, Fun et al., 2007; Patil, Dharmaprakash et al., 2007; Patil et al., 2006), the title compound (I) has recently been prepared in our laboratory and its crystal structure is presented here. The non-centrosymmetric crystal of the title compound should exhibit second-order NLO properties.

The bond lengths and bond angles in (I) have normal values (Allen et al., 1987). The benzene and furyl rings in the molecule are essentially planar with the maximum deviation from planarity being 0.016 (2) Å for atom C10 and 0.003 (2) Å for atom C4 respectively. The dihedral angle between the phenyl and the furyl rings is 41.5 (1)°, indicating that they are twisted from each other.

An intramolecular C—H···O hydrogen bond generates a S(5) ring motif (Bernstein et al., 1995). In the crystal structure, the molecules are stacked along the b axis. The crystal packing is consolidated by C—H···O and C—H···π interactions. π–π interactions with the centroid···centroid(1 -x, y,3 - z) distance of 3.5855 (11) Å is observed.

Related literature top

For related literature on the non-linear optical properties of chromophore derivatives, see: Agrinskaya et al. (1999). For related literature, see: Chantrapromma et al. (2005, 2006); Fun et al. (2006); Patil, Fun et al. (2007); Patil, Dharmaprakash et al. (2007); Patil et al. (2006). For bond-length data, see: Allen et al. (1987). For graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995).

Experimental top

3,4-dimethoxybenzaldehyde (0.01 mol, 1.66 g m) in ethanol (20 ml) was mixed with 2-acetyl furan (0.01 mol, 1.01 ml) in 20 ml ethanol and the mixture was treated with 5 ml of 10% sodium hydroxide solution and stirred at room temperature for 6 h. The precipitate obtained was poured into ice-cold water (500 ml) and left to stand for 5 h. The resulting crude solid was filtered, dried and recrystallized from N,N-dimethylformamide (DMF) by slow evaporation.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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, 2003).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom numbering scheme. The dashed line indicates a hydrogen bond.
	Fig. 2. The crystal packing of the title compound, viewed along the b axis. Hydrogen bonds are shown as dashed lines.

(E)-3-(3,4-Dimethoxyphenyl)-1-(2-furyl)prop-2-en-1-one top

Crystal data top

C₁₅H₁₄O₄	F(000) = 544
M_r = 258.26	D_x = 1.383 Mg m⁻³
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 1982 reflections
a = 21.5582 (5) Å	θ = 3.0–30.0°
b = 5.6105 (1) Å	µ = 0.10 mm⁻¹
c = 10.4622 (3) Å	T = 100 K
β = 101.510 (2)°	Needle, colourless
V = 1239.98 (5) Å³	0.42 × 0.05 × 0.04 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	1997 independent reflections
Radiation source: fine-focus sealed tube	1707 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ϕ and ω scans	θ_max = 30.2°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −30→30
T_min = 0.947, T_max = 0.996	k = −7→7
7017 measured reflections	l = −14→14

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.059P)²] where P = (F_o² + 2F_c²)/3
1997 reflections	(Δ/σ)_max < 0.001
174 parameters	Δρ_max = 0.29 e Å⁻³
1 restraint	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₅H₁₄O₄	V = 1239.98 (5) Å³
M_r = 258.26	Z = 4
Monoclinic, C2	Mo Kα radiation
a = 21.5582 (5) Å	µ = 0.10 mm⁻¹
b = 5.6105 (1) Å	T = 100 K
c = 10.4622 (3) Å	0.42 × 0.05 × 0.04 mm
β = 101.510 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	1997 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1707 reflections with I > 2σ(I)
T_min = 0.947, T_max = 0.996	R_int = 0.033
7017 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	1 restraint
wR(F²) = 0.104	H-atom parameters constrained
S = 1.10	Δρ_max = 0.29 e Å⁻³
1997 reflections	Δρ_min = −0.20 e Å⁻³
174 parameters

Special details top

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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	0.57239 (6)	0.0466 (3)	1.44832 (13)	0.0232 (4)
O2	0.48812 (8)	−0.1128 (3)	1.23361 (16)	0.0332 (4)
O3	0.20877 (6)	0.3835 (3)	0.77192 (13)	0.0207 (3)
O4	0.25511 (6)	0.7519 (3)	0.67784 (12)	0.0205 (3)
C1	0.55488 (9)	0.4315 (4)	1.39689 (18)	0.0214 (5)
H1A	0.5388	0.5703	1.3540	0.026*
C2	0.60096 (9)	0.4149 (5)	1.51546 (19)	0.0243 (5)
H2A	0.6211	0.5408	1.5648	0.029*
C3	0.60942 (8)	0.1816 (5)	1.54141 (19)	0.0235 (5)
H3A	0.6370	0.1201	1.6137	0.028*
C4	0.53928 (8)	0.2049 (4)	1.35948 (17)	0.0186 (4)
C5	0.49518 (9)	0.1039 (4)	1.2480 (2)	0.0208 (4)
C6	0.46005 (8)	0.2776 (4)	1.15509 (17)	0.0195 (4)
H6A	0.4711	0.4380	1.1614	0.023*
C7	0.41218 (8)	0.2036 (4)	1.06159 (18)	0.0197 (4)
H7A	0.4025	0.0420	1.0601	0.024*
C8	0.37371 (8)	0.3532 (4)	0.96152 (17)	0.0177 (4)
C9	0.31001 (8)	0.2882 (4)	0.91378 (17)	0.0178 (4)
H9A	0.2939	0.1504	0.9443	0.021*
C10	0.27144 (8)	0.4282 (4)	0.82177 (17)	0.0178 (4)
C11	0.29632 (8)	0.6304 (4)	0.77127 (17)	0.0164 (4)
C12	0.35917 (8)	0.6949 (4)	0.81736 (18)	0.0189 (4)
H12A	0.3758	0.8294	0.7844	0.023*
C13	0.39718 (8)	0.5570 (4)	0.91321 (18)	0.0189 (4)
H13A	0.4389	0.6026	0.9451	0.023*
C14	0.18004 (8)	0.1967 (4)	0.83195 (19)	0.0209 (4)
H14A	0.1353	0.1960	0.7980	0.031*
H14B	0.1878	0.2219	0.9245	0.031*
H14C	0.1977	0.0465	0.8138	0.031*
C15	0.28193 (10)	0.9223 (5)	0.60272 (19)	0.0232 (4)
H15A	0.2497	0.9791	0.5324	0.035*
H15B	0.3152	0.8484	0.5679	0.035*
H15C	0.2989	1.0537	0.6574	0.035*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0204 (6)	0.0220 (9)	0.0236 (7)	0.0022 (6)	−0.0043 (5)	0.0049 (7)
O2	0.0346 (8)	0.0191 (9)	0.0376 (9)	0.0034 (7)	−0.0128 (7)	0.0013 (9)
O3	0.0168 (5)	0.0235 (9)	0.0198 (6)	−0.0018 (6)	−0.0014 (5)	0.0065 (7)
O4	0.0204 (6)	0.0228 (9)	0.0175 (6)	0.0022 (6)	0.0015 (5)	0.0081 (7)
C1	0.0210 (8)	0.0222 (13)	0.0196 (8)	0.0002 (8)	0.0003 (7)	0.0021 (9)
C2	0.0227 (8)	0.0295 (14)	0.0187 (8)	−0.0004 (9)	−0.0009 (7)	−0.0014 (10)
C3	0.0172 (8)	0.0337 (15)	0.0174 (8)	0.0027 (9)	−0.0021 (6)	0.0028 (10)
C4	0.0158 (7)	0.0211 (11)	0.0173 (8)	0.0028 (8)	−0.0005 (6)	0.0039 (9)
C5	0.0190 (8)	0.0190 (12)	0.0224 (9)	0.0030 (8)	−0.0005 (7)	0.0003 (9)
C6	0.0187 (8)	0.0201 (11)	0.0176 (8)	0.0029 (8)	−0.0012 (6)	0.0009 (9)
C7	0.0193 (8)	0.0173 (11)	0.0205 (9)	0.0012 (8)	−0.0008 (7)	0.0006 (9)
C8	0.0176 (7)	0.0179 (11)	0.0161 (8)	0.0043 (8)	−0.0002 (6)	−0.0015 (9)
C9	0.0197 (8)	0.0159 (11)	0.0168 (8)	0.0014 (7)	0.0015 (6)	−0.0006 (8)
C10	0.0165 (7)	0.0197 (11)	0.0158 (8)	0.0008 (7)	−0.0001 (6)	−0.0015 (9)
C11	0.0182 (8)	0.0169 (11)	0.0133 (8)	0.0021 (7)	0.0015 (6)	−0.0010 (8)
C12	0.0197 (8)	0.0204 (12)	0.0167 (8)	−0.0008 (8)	0.0033 (6)	0.0007 (9)
C13	0.0158 (7)	0.0224 (12)	0.0178 (8)	0.0012 (8)	0.0016 (6)	−0.0026 (9)
C14	0.0189 (8)	0.0234 (12)	0.0194 (8)	−0.0022 (8)	0.0016 (6)	0.0026 (9)
C15	0.0305 (9)	0.0196 (12)	0.0189 (8)	0.0003 (9)	0.0033 (7)	0.0063 (9)

Geometric parameters (Å, º) top

O1—C3	1.360 (3)	C7—C8	1.464 (3)
O1—C4	1.377 (2)	C7—H7A	0.9300
O2—C5	1.231 (3)	C8—C13	1.386 (3)
O3—C10	1.371 (2)	C8—C9	1.412 (2)
O3—C14	1.425 (3)	C9—C10	1.384 (3)
O4—C11	1.365 (2)	C9—H9A	0.9300
O4—C15	1.431 (3)	C10—C11	1.402 (3)
C1—C4	1.353 (3)	C11—C12	1.392 (2)
C1—C2	1.429 (2)	C12—C13	1.396 (3)
C1—H1A	0.9300	C12—H12A	0.9300
C2—C3	1.342 (4)	C13—H13A	0.9300
C2—H2A	0.9300	C14—H14A	0.9600
C3—H3A	0.9300	C14—H14B	0.9600
C4—C5	1.464 (3)	C14—H14C	0.9600
C5—C6	1.475 (3)	C15—H15A	0.9600
C6—C7	1.339 (2)	C15—H15B	0.9600
C6—H6A	0.9300	C15—H15C	0.9600

C3—O1—C4	105.99 (18)	C10—C9—C8	120.4 (2)
C10—O3—C14	116.67 (15)	C10—C9—H9A	119.8
C11—O4—C15	116.78 (14)	C8—C9—H9A	119.8
C4—C1—C2	106.2 (2)	O3—C10—C9	124.77 (19)
C4—C1—H1A	126.9	O3—C10—C11	115.27 (16)
C2—C1—H1A	126.9	C9—C10—C11	119.95 (16)
C3—C2—C1	106.4 (2)	O4—C11—C12	124.57 (19)
C3—C2—H2A	126.8	O4—C11—C10	115.50 (15)
C1—C2—H2A	126.8	C12—C11—C10	119.92 (17)
C2—C3—O1	111.20 (17)	C11—C12—C13	119.73 (19)
C2—C3—H3A	124.4	C11—C12—H12A	120.1
O1—C3—H3A	124.4	C13—C12—H12A	120.1
C1—C4—O1	110.20 (16)	C8—C13—C12	120.98 (16)
C1—C4—C5	132.75 (19)	C8—C13—H13A	119.5
O1—C4—C5	117.05 (19)	C12—C13—H13A	119.5
O2—C5—C4	121.66 (19)	O3—C14—H14A	109.5
O2—C5—C6	122.51 (18)	O3—C14—H14B	109.5
C4—C5—C6	115.8 (2)	H14A—C14—H14B	109.5
C7—C6—C5	119.7 (2)	O3—C14—H14C	109.5
C7—C6—H6A	120.1	H14A—C14—H14C	109.5
C5—C6—H6A	120.1	H14B—C14—H14C	109.5
C6—C7—C8	126.1 (2)	O4—C15—H15A	109.5
C6—C7—H7A	117.0	O4—C15—H15B	109.5
C8—C7—H7A	117.0	H15A—C15—H15B	109.5
C13—C8—C9	118.95 (17)	O4—C15—H15C	109.5
C13—C8—C7	122.56 (16)	H15A—C15—H15C	109.5
C9—C8—C7	118.5 (2)	H15B—C15—H15C	109.5

C4—C1—C2—C3	−0.5 (3)	C7—C8—C9—C10	178.20 (18)
C1—C2—C3—O1	0.2 (3)	C14—O3—C10—C9	8.3 (3)
C4—O1—C3—C2	0.2 (2)	C14—O3—C10—C11	−172.75 (17)
C2—C1—C4—O1	0.6 (2)	C8—C9—C10—O3	−178.34 (19)
C2—C1—C4—C5	179.8 (2)	C8—C9—C10—C11	2.8 (3)
C3—O1—C4—C1	−0.5 (2)	C15—O4—C11—C12	14.7 (3)
C3—O1—C4—C5	−179.81 (17)	C15—O4—C11—C10	−165.54 (18)
C1—C4—C5—O2	−179.5 (2)	O3—C10—C11—O4	−1.2 (2)
O1—C4—C5—O2	−0.4 (3)	C9—C10—C11—O4	177.80 (18)
C1—C4—C5—C6	0.5 (3)	O3—C10—C11—C12	178.59 (18)
O1—C4—C5—C6	179.55 (16)	C9—C10—C11—C12	−2.4 (3)
O2—C5—C6—C7	9.9 (3)	O4—C11—C12—C13	−179.89 (18)
C4—C5—C6—C7	−170.05 (18)	C10—C11—C12—C13	0.3 (3)
C5—C6—C7—C8	−178.99 (19)	C9—C8—C13—C12	−1.0 (3)
C6—C7—C8—C13	29.9 (3)	C7—C8—C13—C12	179.74 (19)
C6—C7—C8—C9	−149.4 (2)	C11—C12—C13—C8	1.4 (3)
C13—C8—C9—C10	−1.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O2ⁱ	0.93	2.32	3.247 (3)	173
C3—H3A···O3ⁱⁱ	0.93	2.42	3.338 (3)	167
C7—H7A···O2	0.93	2.47	2.810 (3)	101
C14—H14B···Cg1ⁱⁱⁱ	0.96	2.66	3.431 (2)	137

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄O₄
M_r	258.26
Crystal system, space group	Monoclinic, C2
Temperature (K)	100
a, b, c (Å)	21.5582 (5), 5.6105 (1), 10.4622 (3)
β (°)	101.510 (2)
V (Å³)	1239.98 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.42 × 0.05 × 0.04

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.947, 0.996
No. of measured, independent and observed [I > 2σ(I)] reflections	7017, 1997, 1707
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.707

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.104, 1.10
No. of reflections	1997
No. of parameters	174
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.20

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O2ⁱ	0.93	2.32	3.247 (3)	173
C3—H3A···O3ⁱⁱ	0.93	2.42	3.338 (3)	167
C7—H7A···O2	0.93	2.47	2.810 (3)	101
C14—H14B···Cg1ⁱⁱⁱ	0.96	2.66	3.431 (2)	137

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

Footnotes

‡Permanent address: Department of Physics, Karunya University, Karunya Nagar, Coimbatore 641 114, India.

Acknowledgements

HKF and SRJ thank the Malaysian Government and Universiti Sains Malaysia for Science Fund grant No. 305/PFIZIK/613312. SRJ thanks the Universiti Sains Malaysia for a post-doctoral research fellowship. This work was supported by the Department of Science and Technology (DST), Government of India (grant No. SR/S2/LOP-17/2006).

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