3-[4-(Dimethyl­amino)phen­yl]-1-(2-pyrrol­yl)prop-2-en-1-one

Tang, S.-P.; Kuang, D.-Z.; Feng, Y.-L.; Li, W.; Chen, Z.-M.

doi:10.1107/S1600536808014700

organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o1123

doi:10.1107/S1600536808014700

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3-[4-(Dimethylamino)phenyl]-1-(2-pyrrolyl)prop-2-en-1-one

Si-Ping Tang,^a ^* Dai-Zhi Kuang,^a Yong-Lan Feng,^a Wei Li ^a and Zhi-Min Chen ^a

^aDepartment of Chemistry and Materials Science, Hengyang Normal University, Hengyang, Hunan 421008, People's Republic of China
^*Correspondence e-mail: sptang88@163.com

(Received 1 March 2008; accepted 15 May 2008; online 21 May 2008)

The molecule of the title compound, C₁₅H₁₆N₂O, is non-planar with a dihedral angle of 16.0 (1)° between the pyrrole and benzene rings. The ketone double-bond displays an s–cis conformation with an O=C—C=C torsion angle of 7.9 (3) and an intramolecular C—H⋯O hydrogen bond. In the crystal structure, adjacent molecules are paired through N—H⋯O hydrogen bonds into centrosymmetric dimers.

Related literature

For the pharmaceutical and biological activities of chalcones, see: Lin et al. (2002 ); Lunardi et al. (2003 ); Modzelewska et al. (2006 ); Opletalova (2000 ); Opletalova & Sedivy (1999 ); Sogawa et al. (1994 ). For the use of chalcones as photonic materials, see: Balaji et al. (2003 ); Indira et al. (2002 ).

Experimental

Crystal data

C₁₅H₁₆N₂O
M_r = 240.30
Monoclinic, P 2₁ /c
a = 11.0864 (16) Å
b = 12.0412 (17) Å
c = 10.6169 (16) Å
β = 112.294 (2)°
V = 1311.3 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 (2) K
0.20 × 0.18 × 0.17 mm

Data collection

Bruker APEX area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.985, T_max = 0.991
6889 measured reflections
2568 independent reflections
1654 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.065
wR(F²) = 0.159
S = 1.09
2568 reflections
165 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1ⁱ	0.86	2.01	2.832 (2)	161
C7—H7⋯O1	0.93	2.44	2.797 (3)	103
Symmetry code: (i) -x+1, -y, -z+2.

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808014700/ez2122sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808014700/ez2122Isup2.hkl

checkCIF report

Comment top

Chalcones and their analogues are of considerable interest because they possess broad pharmaceutical (Sogawa et al., 1994) and biological activities (Opletalova & Sedivy, 1999), such as anticancer (Modzelewska et al., 2006), antitubercular (Lin et al., 2002), trypanocidal (Lunardi et al., 2003), antifungal and antibacterial properties (Opletalova, 2000). Moreover, some substituted chalcones have also been studied as negative photoresist materials (Balaji et al., 2003) and non-linear optical materials (Indira et al., 2002). We report here a new chalcone compound, (I), Fig. 1.

The title compound reveals an s-cis conformation for the O1–C5–C6–C7 [torsion angle 7.9 (3)°] ketone motif. Differently to most substituted chalcones, compound (I) is nonplanar with a dihedral angle between the pyrrole ring and benzene ring of 16.0 (1)°. In the crystal packing, the –NH groups are involved as donors to form centrosymmetric dimers through N—H···O hydrogen bonding interactions as shown in Fig. 2.

Related literature top

For the pharmaceutical and biological activities of chalcones, see: Lin et al. (2002); Lunardi et al. (2003); Modzelewska et al. (2006); Opletalova (2000); Opletalova & Sedivy (1999); Sogawa et al. (1994). For chalcones as photo materials, see: Balaji et al. (2003); Indira et al. (2002).

Experimental top

To a solution of 2-acetylpyrrole (1.09 g, 10.0 mmol) and 4-dimethylaminobenzaldehyde (1.49 g, 10.0 mmol) in 15 ml e thanol was added a solution of sodium hydroxide (0.40 g, 10.0 mmol) in 5 ml water at room temperature. After stirring 10 h, the solution was filtered. The resulting orange precipitate was washed with water and iced ethanol, and further recrystallized from acetone to afford orange block crystals of the title compound. Yield: 0.92 g (38.3%).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I) showing the atom numbering scheme, with displacement ellipsoids drawn at the 30% probability level, and H atoms as spheres of arbitrary radius.
	Fig. 2. Partial packing diagram of the title structure showing the N—H···O hydrogen bonding interactions as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity.

3-[4-(Dimethylamino)phenyl]-1-(2-pyrrolyl)prop-2-en-1-one top

Crystal data top

C₁₅H₁₆N₂O	F(000) = 512
M_r = 240.30	D_x = 1.217 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1115 reflections
a = 11.0864 (16) Å	θ = 2.6–23.4°
b = 12.0412 (17) Å	µ = 0.08 mm⁻¹
c = 10.6169 (16) Å	T = 293 K
β = 112.294 (2)°	Block, orange
V = 1311.3 (3) Å³	0.20 × 0.18 × 0.17 mm
Z = 4

Data collection top

Bruker APEX area-detector diffractometer	2568 independent reflections
Radiation source: fine-focus sealed tube	1654 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
T_min = 0.985, T_max = 0.991	k = −14→9
6889 measured reflections	l = −10→13

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.159	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0637P)² + 0.0839P] where P = (F_o² + 2F_c²)/3
2568 reflections	(Δ/σ)_max < 0.001
165 parameters	Δρ_max = 0.13 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₅H₁₆N₂O	V = 1311.3 (3) Å³
M_r = 240.30	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.0864 (16) Å	µ = 0.08 mm⁻¹
b = 12.0412 (17) Å	T = 293 K
c = 10.6169 (16) Å	0.20 × 0.18 × 0.17 mm
β = 112.294 (2)°

Data collection top

Bruker APEX area-detector diffractometer	2568 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1654 reflections with I > 2σ(I)
T_min = 0.985, T_max = 0.991	R_int = 0.040
6889 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	0 restraints
wR(F²) = 0.159	H-atom parameters constrained
S = 1.09	Δρ_max = 0.13 e Å⁻³
2568 reflections	Δρ_min = −0.15 e Å⁻³
165 parameters

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	0.39484 (17)	0.01511 (13)	0.82369 (16)	0.0848 (6)
N1	0.53628 (17)	0.17431 (15)	1.00559 (18)	0.0683 (6)
H1A	0.5418	0.1100	1.0427	0.082*
N2	−0.1228 (2)	0.10473 (18)	0.0104 (2)	0.0821 (6)
C1	0.4663 (2)	0.19776 (18)	0.8722 (2)	0.0583 (6)
C2	0.4841 (2)	0.30924 (19)	0.8553 (3)	0.0726 (7)
H2	0.4480	0.3488	0.7744	0.087*
C3	0.5650 (2)	0.3521 (2)	0.9796 (3)	0.0831 (8)
H3	0.5933	0.4252	0.9977	0.100*
C4	0.5953 (3)	0.2667 (2)	1.0701 (3)	0.0823 (8)
H4	0.6483	0.2716	1.1619	0.099*
C5	0.3924 (2)	0.11169 (19)	0.7811 (2)	0.0621 (6)
C6	0.3125 (2)	0.14088 (19)	0.6406 (2)	0.0628 (6)
H6	0.3205	0.2111	0.6082	0.075*
C7	0.2285 (2)	0.06891 (18)	0.5581 (2)	0.0642 (6)
H7	0.2257	0.0000	0.5965	0.077*
C8	0.1409 (2)	0.08166 (17)	0.4178 (2)	0.0581 (6)
C9	0.0498 (3)	−0.00039 (19)	0.3551 (3)	0.0776 (7)
H9	0.0479	−0.0632	0.4052	0.093*
C10	−0.0371 (2)	0.0067 (2)	0.2234 (2)	0.0768 (7)
H10	−0.0960	−0.0509	0.1868	0.092*
C11	−0.0389 (2)	0.09835 (19)	0.1430 (2)	0.0623 (6)
C12	0.0526 (2)	0.18180 (18)	0.2049 (2)	0.0666 (6)
H12	0.0547	0.2448	0.1550	0.080*
C13	0.1389 (2)	0.17297 (17)	0.3365 (2)	0.0635 (6)
H13	0.1984	0.2300	0.3733	0.076*
C14	−0.2165 (3)	0.0175 (2)	−0.0521 (3)	0.0945 (9)
H14A	−0.1716	−0.0517	−0.0454	0.142*
H14B	−0.2642	0.0350	−0.1462	0.142*
H14C	−0.2759	0.0115	−0.0061	0.142*
C15	−0.1296 (3)	0.2014 (3)	−0.0725 (3)	0.1092 (10)
H15A	−0.1863	0.2556	−0.0575	0.164*
H15B	−0.1630	0.1804	−0.1667	0.164*
H15C	−0.0440	0.2325	−0.0482	0.164*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.1096 (14)	0.0608 (11)	0.0631 (11)	−0.0019 (9)	0.0093 (9)	0.0103 (8)
N1	0.0763 (13)	0.0619 (12)	0.0593 (12)	−0.0020 (10)	0.0172 (10)	0.0020 (9)
N2	0.0801 (14)	0.0857 (15)	0.0640 (14)	0.0035 (11)	0.0088 (11)	0.0010 (11)
C1	0.0588 (12)	0.0576 (14)	0.0562 (13)	0.0046 (10)	0.0192 (11)	0.0052 (11)
C2	0.0758 (15)	0.0639 (16)	0.0775 (18)	0.0004 (12)	0.0285 (14)	0.0081 (12)
C3	0.0896 (18)	0.0669 (16)	0.093 (2)	−0.0156 (14)	0.0349 (16)	−0.0078 (16)
C4	0.0858 (18)	0.0832 (19)	0.0690 (17)	−0.0157 (15)	0.0194 (14)	−0.0152 (15)
C5	0.0649 (14)	0.0598 (14)	0.0585 (14)	0.0063 (11)	0.0199 (11)	0.0057 (11)
C6	0.0656 (13)	0.0544 (13)	0.0620 (14)	0.0034 (11)	0.0170 (12)	0.0068 (11)
C7	0.0714 (14)	0.0535 (13)	0.0654 (15)	0.0062 (11)	0.0233 (13)	0.0068 (11)
C8	0.0620 (13)	0.0502 (13)	0.0600 (14)	0.0041 (10)	0.0207 (11)	0.0024 (10)
C9	0.0934 (18)	0.0617 (15)	0.0680 (17)	−0.0140 (13)	0.0195 (14)	0.0066 (12)
C10	0.0816 (17)	0.0723 (17)	0.0676 (17)	−0.0216 (13)	0.0182 (14)	−0.0045 (13)
C11	0.0607 (13)	0.0655 (15)	0.0574 (14)	0.0096 (11)	0.0188 (11)	−0.0016 (11)
C12	0.0732 (15)	0.0580 (14)	0.0633 (15)	0.0044 (12)	0.0199 (13)	0.0104 (11)
C13	0.0623 (13)	0.0550 (14)	0.0662 (15)	−0.0023 (10)	0.0164 (12)	0.0014 (11)
C14	0.0762 (17)	0.115 (2)	0.0791 (19)	−0.0055 (16)	0.0143 (15)	−0.0205 (16)
C15	0.116 (2)	0.114 (2)	0.0713 (19)	0.0082 (19)	0.0052 (17)	0.0173 (17)

Geometric parameters (Å, º) top

O1—C5	1.244 (2)	C7—H7	0.9300
N1—C4	1.339 (3)	C8—C9	1.388 (3)
N1—C1	1.361 (3)	C8—C13	1.392 (3)
N1—H1A	0.8600	C9—C10	1.367 (3)
N2—C11	1.364 (3)	C9—H9	0.9300
N2—C15	1.443 (3)	C10—C11	1.391 (3)
N2—C14	1.449 (3)	C10—H10	0.9300
C1—C2	1.379 (3)	C11—C12	1.402 (3)
C1—C5	1.442 (3)	C12—C13	1.366 (3)
C2—C3	1.383 (3)	C12—H12	0.9300
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.360 (3)	C14—H14A	0.9600
C3—H3	0.9300	C14—H14B	0.9600
C4—H4	0.9300	C14—H14C	0.9600
C5—C6	1.460 (3)	C15—H15A	0.9600
C6—C7	1.329 (3)	C15—H15B	0.9600
C6—H6	0.9300	C15—H15C	0.9600
C7—C8	1.446 (3)

C4—N1—C1	109.6 (2)	C13—C8—C7	124.7 (2)
C4—N1—H1A	125.2	C10—C9—C8	123.2 (2)
C1—N1—H1A	125.2	C10—C9—H9	118.4
C11—N2—C15	122.1 (2)	C8—C9—H9	118.4
C11—N2—C14	121.4 (2)	C9—C10—C11	121.1 (2)
C15—N2—C14	116.3 (2)	C9—C10—H10	119.4
N1—C1—C2	106.5 (2)	C11—C10—H10	119.4
N1—C1—C5	120.2 (2)	N2—C11—C10	121.6 (2)
C2—C1—C5	133.3 (2)	N2—C11—C12	122.2 (2)
C1—C2—C3	108.2 (2)	C10—C11—C12	116.3 (2)
C1—C2—H2	125.9	C13—C12—C11	121.7 (2)
C3—C2—H2	125.9	C13—C12—H12	119.2
C4—C3—C2	106.8 (2)	C11—C12—H12	119.2
C4—C3—H3	126.6	C12—C13—C8	122.4 (2)
C2—C3—H3	126.6	C12—C13—H13	118.8
N1—C4—C3	109.0 (2)	C8—C13—H13	118.8
N1—C4—H4	125.5	N2—C14—H14A	109.5
C3—C4—H4	125.5	N2—C14—H14B	109.5
O1—C5—C1	119.9 (2)	H14A—C14—H14B	109.5
O1—C5—C6	121.2 (2)	N2—C14—H14C	109.5
C1—C5—C6	118.9 (2)	H14A—C14—H14C	109.5
C7—C6—C5	121.2 (2)	H14B—C14—H14C	109.5
C7—C6—H6	119.4	N2—C15—H15A	109.5
C5—C6—H6	119.4	N2—C15—H15B	109.5
C6—C7—C8	129.7 (2)	H15A—C15—H15B	109.5
C6—C7—H7	115.2	N2—C15—H15C	109.5
C8—C7—H7	115.2	H15A—C15—H15C	109.5
C9—C8—C13	115.3 (2)	H15B—C15—H15C	109.5
C9—C8—C7	120.0 (2)

C4—N1—C1—C2	0.2 (3)	C6—C7—C8—C13	7.1 (4)
C4—N1—C1—C5	−179.3 (2)	C13—C8—C9—C10	−0.4 (4)
N1—C1—C2—C3	−0.1 (3)	C7—C8—C9—C10	179.2 (2)
C5—C1—C2—C3	179.4 (2)	C8—C9—C10—C11	0.1 (4)
C1—C2—C3—C4	0.0 (3)	C15—N2—C11—C10	177.3 (3)
C1—N1—C4—C3	−0.2 (3)	C14—N2—C11—C10	1.7 (3)
C2—C3—C4—N1	0.1 (3)	C15—N2—C11—C12	−4.6 (4)
N1—C1—C5—O1	−1.6 (3)	C14—N2—C11—C12	179.8 (2)
C2—C1—C5—O1	179.0 (2)	C9—C10—C11—N2	178.2 (2)
N1—C1—C5—C6	176.55 (19)	C9—C10—C11—C12	0.0 (4)
C2—C1—C5—C6	−2.9 (4)	N2—C11—C12—C13	−178.0 (2)
O1—C5—C6—C7	7.9 (3)	C10—C11—C12—C13	0.2 (3)
C1—C5—C6—C7	−170.3 (2)	C11—C12—C13—C8	−0.5 (4)
C5—C6—C7—C8	179.5 (2)	C9—C8—C13—C12	0.6 (3)
C6—C7—C8—C9	−172.4 (2)	C7—C8—C13—C12	−179.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.86	2.01	2.832 (2)	161
C7—H7···O1	0.93	2.44	2.797 (3)	103

Symmetry code: (i) −x+1, −y, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₆N₂O
M_r	240.30
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	11.0864 (16), 12.0412 (17), 10.6169 (16)
β (°)	112.294 (2)
V (Å³)	1311.3 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.20 × 0.18 × 0.17

Data collection
Diffractometer	Bruker APEX area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.985, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	6889, 2568, 1654
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.159, 1.09
No. of reflections	2568
No. of parameters	165
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.15

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.86	2.01	2.832 (2)	161.0
C7—H7···O1	0.93	2.44	2.797 (3)	103.0

Symmetry code: (i) −x+1, −y, −z+2.

Acknowledgements

The authors thank Hengyang Normal University for supporting this study.

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