

Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807041852/sj2339sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536807041852/sj2339Isup2.hkl |
CCDC reference: 663674
2-Acetylpyrrole (4.36 g, 40.0 mmol) was added to a solution of p-tolualdehyde (2.42 g, 20.0 mmol) in methanol (130 ml). Potassium hydroxide (2.24 g, 40 mmol) and ammonia (25%, 100 ml) were then added to the solution and refluxed for 36 h. The yellow precipitate that formed was removed by vacuum filtration, washed with water to neutral pH. The product was recrystallized from chloroform/ethanol (3:1) to yield 2.10 g (49%) of the title compound.
All H-atoms were positioned geometrically and refined using a riding model with C—H = 0.93 Å and N—H = 0.86 Å, Uiso = 1.2Ueq(C or N) for aromatic, ethylene and nitrogen; 0.96 Å, Uiso = 1.5Ueq(C) for CH3 atoms.
Chalcones have attracted considerable interest as a template in the development of biology. The anticancer, antibacterial, antiviral, antiprotozoal, insecticidal and enzyme-inhibitory properties of a number of chalcones have been reviewed (Dimmock et al., 1999; Go et al., 2005; Opletalova, 2000; Opletalova & Sedivy, 1999). The objective of this study therefore synthesize and elucidate the crystal structure of a new chalcone compound, (I), Fig. 1.
The pyrrole ring, benzene ring and the enone group of the molecule containing atoms O1, C5, C6 and C7, are almost co-planar with the maximum deviation 0.0702 Å for C7. The short H6···H9 (2.25 Å) contact causes the bond angles C7—C8—C9 [123.1 (2)°] C6—C7—C8 [127.7 (1)°] to deviate significantly from 120°.
In the crystal, molecules form inversion related dimers through N—H···O hydrogen bonds. Neighboring pairs are further linked by face-to-face π–π stacking interactions between adjacent pyrrole rings [perpendicular interplanar distance 3.3948 (3) Å and centroid-to-centroid distance 3.723 (2) Å], forming one-dimensional chains, Fig. 2.
For details of the biological properties of chalcones, see: Dimmock et al. (1999); Go et al. (2005); Opletalova (2000); Opletalova & Sedivy (1999). For related structures, see: Kumaran et al. (1996); Shanmuga Sundara Raj et al., (1997, 1998).
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXTL (Bruker, 2002).
C14H13NO | F(000) = 448 |
Mr = 211.25 | Dx = 1.217 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P2ybc | Cell parameters from 1908 reflections |
a = 8.6236 (11) Å | θ = 2.4–26.2° |
b = 5.6273 (7) Å | µ = 0.08 mm−1 |
c = 23.958 (3) Å | T = 295 K |
β = 97.305 (2)° | Prism, yellow |
V = 1153.2 (3) Å3 | 0.43 × 0.22 × 0.18 mm |
Z = 4 |
Bruker APEX area-detector diffractometer | 2241 independent reflections |
Radiation source: fine-focus sealed tube | 1757 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
φ and ω scans | θmax = 26.0°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→10 |
Tmin = 0.892, Tmax = 0.985 | k = −6→6 |
6514 measured reflections | l = −29→29 |
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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.145 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0733P)2 + 0.198P] where P = (Fo2 + 2Fc2)/3 |
2241 reflections | (Δ/σ)max < 0.001 |
146 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
C14H13NO | V = 1153.2 (3) Å3 |
Mr = 211.25 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.6236 (11) Å | µ = 0.08 mm−1 |
b = 5.6273 (7) Å | T = 295 K |
c = 23.958 (3) Å | 0.43 × 0.22 × 0.18 mm |
β = 97.305 (2)° |
Bruker APEX area-detector diffractometer | 2241 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1757 reflections with I > 2σ(I) |
Tmin = 0.892, Tmax = 0.985 | Rint = 0.022 |
6514 measured reflections |
R[F2 > 2σ(F2)] = 0.051 | 0 restraints |
wR(F2) = 0.145 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.22 e Å−3 |
2241 reflections | Δρmin = −0.20 e Å−3 |
146 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.41397 (15) | 0.4506 (2) | 0.42156 (5) | 0.0652 (4) | |
N1 | 0.65056 (16) | 0.2223 (3) | 0.49341 (6) | 0.0550 (4) | |
H1 | 0.6209 | 0.3507 | 0.5084 | 0.066* | |
C1 | 0.10198 (19) | −0.0007 (3) | 0.15386 (7) | 0.0524 (4) | |
C2 | 0.2228 (2) | −0.1227 (3) | 0.18472 (8) | 0.0610 (5) | |
H2 | 0.2580 | −0.2638 | 0.1705 | 0.073* | |
C3 | 0.2927 (2) | −0.0405 (3) | 0.23608 (8) | 0.0628 (5) | |
H3 | 0.3739 | −0.1269 | 0.2558 | 0.075* | |
C4 | 0.24344 (18) | 0.1698 (3) | 0.25891 (7) | 0.0500 (4) | |
C5 | 0.1241 (2) | 0.2946 (3) | 0.22729 (7) | 0.0565 (5) | |
H5 | 0.0903 | 0.4378 | 0.2409 | 0.068* | |
C6 | 0.0545 (2) | 0.2104 (3) | 0.17596 (7) | 0.0587 (5) | |
H6 | −0.0257 | 0.2973 | 0.1559 | 0.070* | |
C7 | 0.0241 (2) | −0.0992 (4) | 0.09886 (8) | 0.0699 (6) | |
H7A | 0.0887 | −0.0688 | 0.0698 | 0.105* | |
H7B | −0.0757 | −0.0241 | 0.0893 | 0.105* | |
H7C | 0.0098 | −0.2674 | 0.1024 | 0.105* | |
C8 | 0.30938 (19) | 0.2592 (3) | 0.31416 (7) | 0.0532 (4) | |
H8 | 0.2768 | 0.4098 | 0.3237 | 0.064* | |
C9 | 0.40985 (19) | 0.1515 (3) | 0.35225 (7) | 0.0566 (5) | |
H9 | 0.4450 | 0.0004 | 0.3443 | 0.068* | |
C10 | 0.46818 (18) | 0.2609 (3) | 0.40658 (7) | 0.0521 (4) | |
C11 | 0.59111 (18) | 0.1372 (3) | 0.44173 (7) | 0.0495 (4) | |
C12 | 0.6710 (2) | −0.0694 (3) | 0.43344 (8) | 0.0589 (5) | |
H12 | 0.6556 | −0.1664 | 0.4018 | 0.071* | |
C13 | 0.7789 (2) | −0.1066 (4) | 0.48098 (8) | 0.0669 (5) | |
H13 | 0.8493 | −0.2320 | 0.4869 | 0.080* | |
C14 | 0.7621 (2) | 0.0753 (3) | 0.51726 (8) | 0.0627 (5) | |
H14 | 0.8186 | 0.0943 | 0.5527 | 0.075* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0716 (8) | 0.0628 (8) | 0.0578 (8) | 0.0086 (6) | −0.0054 (6) | −0.0152 (6) |
N1 | 0.0557 (8) | 0.0583 (8) | 0.0494 (8) | 0.0015 (7) | 0.0008 (6) | −0.0053 (7) |
C1 | 0.0536 (9) | 0.0589 (10) | 0.0450 (9) | −0.0076 (8) | 0.0074 (7) | −0.0022 (8) |
C2 | 0.0626 (10) | 0.0620 (11) | 0.0579 (11) | 0.0063 (9) | 0.0055 (8) | −0.0173 (9) |
C3 | 0.0562 (9) | 0.0701 (12) | 0.0590 (11) | 0.0146 (9) | −0.0041 (8) | −0.0137 (9) |
C4 | 0.0478 (8) | 0.0540 (10) | 0.0478 (9) | −0.0044 (7) | 0.0048 (7) | −0.0057 (7) |
C5 | 0.0698 (11) | 0.0469 (9) | 0.0520 (10) | 0.0039 (8) | 0.0050 (8) | −0.0030 (8) |
C6 | 0.0656 (10) | 0.0595 (10) | 0.0483 (10) | 0.0061 (8) | −0.0025 (8) | 0.0035 (8) |
C7 | 0.0754 (12) | 0.0805 (14) | 0.0513 (10) | −0.0049 (10) | −0.0013 (9) | −0.0107 (9) |
C8 | 0.0524 (9) | 0.0557 (10) | 0.0517 (10) | −0.0034 (7) | 0.0072 (8) | −0.0099 (8) |
C9 | 0.0536 (9) | 0.0600 (10) | 0.0544 (10) | 0.0008 (8) | −0.0001 (8) | −0.0125 (8) |
C10 | 0.0473 (8) | 0.0564 (10) | 0.0523 (10) | −0.0052 (7) | 0.0055 (7) | −0.0071 (8) |
C11 | 0.0468 (8) | 0.0562 (10) | 0.0454 (9) | −0.0066 (7) | 0.0044 (7) | −0.0045 (7) |
C12 | 0.0599 (10) | 0.0595 (11) | 0.0576 (10) | −0.0013 (8) | 0.0093 (8) | −0.0070 (9) |
C13 | 0.0639 (11) | 0.0679 (12) | 0.0676 (12) | 0.0120 (9) | 0.0033 (9) | 0.0052 (10) |
C14 | 0.0601 (10) | 0.0723 (12) | 0.0531 (10) | 0.0000 (9) | −0.0025 (8) | 0.0044 (9) |
O1—C10 | 1.237 (2) | C6—H6 | 0.9300 |
N1—C14 | 1.340 (2) | C7—H7A | 0.9600 |
N1—C11 | 1.365 (2) | C7—H7B | 0.9600 |
N1—H1 | 0.8600 | C7—H7C | 0.9600 |
C1—C2 | 1.382 (2) | C8—C9 | 1.323 (2) |
C1—C6 | 1.384 (2) | C8—H8 | 0.9300 |
C1—C7 | 1.506 (2) | C9—C10 | 1.470 (2) |
C2—C3 | 1.379 (2) | C9—H9 | 0.9300 |
C2—H2 | 0.9300 | C10—C11 | 1.446 (2) |
C3—C4 | 1.393 (2) | C11—C12 | 1.379 (2) |
C3—H3 | 0.9300 | C12—C13 | 1.392 (2) |
C4—C5 | 1.389 (2) | C12—H12 | 0.9300 |
C4—C8 | 1.462 (2) | C13—C14 | 1.362 (3) |
C5—C6 | 1.381 (2) | C13—H13 | 0.9300 |
C5—H5 | 0.9300 | C14—H14 | 0.9300 |
C14—N1—C11 | 109.67 (15) | C1—C7—H7C | 109.5 |
C14—N1—H1 | 125.2 | H7A—C7—H7C | 109.5 |
C11—N1—H1 | 125.2 | H7B—C7—H7C | 109.5 |
C2—C1—C6 | 117.49 (15) | C9—C8—C4 | 127.73 (17) |
C2—C1—C7 | 120.48 (17) | C9—C8—H8 | 116.1 |
C6—C1—C7 | 122.02 (16) | C4—C8—H8 | 116.1 |
C3—C2—C1 | 121.66 (17) | C8—C9—C10 | 122.63 (17) |
C3—C2—H2 | 119.2 | C8—C9—H9 | 118.7 |
C1—C2—H2 | 119.2 | C10—C9—H9 | 118.7 |
C2—C3—C4 | 121.01 (16) | O1—C10—C11 | 121.51 (15) |
C2—C3—H3 | 119.5 | O1—C10—C9 | 121.28 (15) |
C4—C3—H3 | 119.5 | C11—C10—C9 | 117.21 (15) |
C5—C4—C3 | 117.21 (15) | N1—C11—C12 | 106.82 (14) |
C5—C4—C8 | 119.73 (15) | N1—C11—C10 | 121.50 (15) |
C3—C4—C8 | 123.05 (15) | C12—C11—C10 | 131.68 (15) |
C6—C5—C4 | 121.33 (16) | C11—C12—C13 | 107.66 (16) |
C6—C5—H5 | 119.3 | C11—C12—H12 | 126.2 |
C4—C5—H5 | 119.3 | C13—C12—H12 | 126.2 |
C5—C6—C1 | 121.27 (16) | C14—C13—C12 | 107.15 (17) |
C5—C6—H6 | 119.4 | C14—C13—H13 | 126.4 |
C1—C6—H6 | 119.4 | C12—C13—H13 | 126.4 |
C1—C7—H7A | 109.5 | N1—C14—C13 | 108.70 (16) |
C1—C7—H7B | 109.5 | N1—C14—H14 | 125.7 |
H7A—C7—H7B | 109.5 | C13—C14—H14 | 125.7 |
C6—C1—C2—C3 | 1.0 (3) | C8—C9—C10—O1 | 7.2 (3) |
C7—C1—C2—C3 | −177.82 (18) | C8—C9—C10—C11 | −172.94 (16) |
C1—C2—C3—C4 | 0.1 (3) | C14—N1—C11—C12 | −0.66 (19) |
C2—C3—C4—C5 | −1.4 (3) | C14—N1—C11—C10 | 179.84 (15) |
C2—C3—C4—C8 | 177.45 (18) | O1—C10—C11—N1 | 1.2 (3) |
C3—C4—C5—C6 | 1.6 (3) | C9—C10—C11—N1 | −178.62 (15) |
C8—C4—C5—C6 | −177.28 (16) | O1—C10—C11—C12 | −178.12 (17) |
C4—C5—C6—C1 | −0.5 (3) | C9—C10—C11—C12 | 2.0 (3) |
C2—C1—C6—C5 | −0.8 (3) | N1—C11—C12—C13 | 0.1 (2) |
C7—C1—C6—C5 | 178.01 (18) | C10—C11—C12—C13 | 179.52 (18) |
C5—C4—C8—C9 | 171.77 (17) | C11—C12—C13—C14 | 0.5 (2) |
C3—C4—C8—C9 | −7.0 (3) | C11—N1—C14—C13 | 1.0 (2) |
C4—C8—C9—C10 | 179.85 (16) | C12—C13—C14—N1 | −0.9 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.86 | 2.07 | 2.8525 (19) | 151 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C14H13NO |
Mr | 211.25 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 295 |
a, b, c (Å) | 8.6236 (11), 5.6273 (7), 23.958 (3) |
β (°) | 97.305 (2) |
V (Å3) | 1153.2 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.43 × 0.22 × 0.18 |
Data collection | |
Diffractometer | Bruker APEX area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.892, 0.985 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6514, 2241, 1757 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.145, 1.05 |
No. of reflections | 2241 |
No. of parameters | 146 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.22, −0.20 |
Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2002).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.86 | 2.07 | 2.8525 (19) | 150.9 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Chalcones have attracted considerable interest as a template in the development of biology. The anticancer, antibacterial, antiviral, antiprotozoal, insecticidal and enzyme-inhibitory properties of a number of chalcones have been reviewed (Dimmock et al., 1999; Go et al., 2005; Opletalova, 2000; Opletalova & Sedivy, 1999). The objective of this study therefore synthesize and elucidate the crystal structure of a new chalcone compound, (I), Fig. 1.
The pyrrole ring, benzene ring and the enone group of the molecule containing atoms O1, C5, C6 and C7, are almost co-planar with the maximum deviation 0.0702 Å for C7. The short H6···H9 (2.25 Å) contact causes the bond angles C7—C8—C9 [123.1 (2)°] C6—C7—C8 [127.7 (1)°] to deviate significantly from 120°.
In the crystal, molecules form inversion related dimers through N—H···O hydrogen bonds. Neighboring pairs are further linked by face-to-face π–π stacking interactions between adjacent pyrrole rings [perpendicular interplanar distance 3.3948 (3) Å and centroid-to-centroid distance 3.723 (2) Å], forming one-dimensional chains, Fig. 2.