


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807063489/fb2072sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536807063489/fb2072Isup2.hkl |
CCDC reference: 674477
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean
(C-C) = 0.003 Å
- R factor = 0.054
- wR factor = 0.137
- Data-to-parameter ratio = 15.2
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
2-Acetylpyrrole (2.18 g, 20.0 mmol) was added to a solution of benzaldehyde (1.06 g, 10.0 mmol) in methanol (65 ml). Then potassium hydroxide (1.12 g, 20 mmol) and ammonia (25%, 50 ml) were added to the solution and refluxed for 12 h. The resulting solution was cooled and the solvent was evaporated under vacuum to give an orange precipitate which was separated by filtration, washed with iced ethanol (95%) and water to pH = 7. Recrystallization from dichloromethane gave light yellow prism-like crystals with average size of about 1.50x0.35x0.25 mm. Yield: 0.89 g (45%).
All the H atoms could be distinguished in the difference Fourier map. Nevertheless, the H atoms were set into idealized positions and constrained by the riding motion formalism: The C—H and N—H distances were set to 0.93 and 0.86 Å, respectively, while Uiso=1.2Ueq of the pertinent carrier atom.
Chalcone derivatives possess wide variety of pharmaceutical properties, such as anticancer, antibacterial, antiviral, antiprotozoal, insecticidal and enzyme-inhibitory ones (Dimmock et al., 1999; Go et al., 2005; Opletalova, 2000). Some of the substituted chalcones are also reported to possess antileishmanial (Chen et al., 1999), antitubercular (Lin et al., 2002), trypanocidal (Lunardi et al., 2003) activities. As a part of our ongoing efforts in the chalcone compounds (Gong & Shen, 2007), the title compound is reported here for the first time.
In the title compound, C13H11NO, the bond lengths and angles are usual. The –NH groups are involved as donors to form centrosymmetric dimers with a motif R22(10) through N—H···O hydrogen bonds (Etter et al., 1990) - (Fig. 2). There is a pyrrole-H···π-phenyl-ring interaction as indicate the geometric parameters C2—H2···Centroid(phenyl) (1 - x, y, 3/2 - z) where the distance H···centroid and C2···centroid equal to 2.90 and 3.666 (3) Å, respectively, and the angle C2—H2···Centroid(phenyl) equals to 141° (Spek, 2003).
For details of the biological and the pharmaceutical properties of chalcones, see: Chen et al. (1999); Dimmock et al. (1999); Go et al. (2005); Lin et al. (2002); Lunardi et al. (2003); Opletalova (2000). For other related literature, see: Gong & Shen (2007); Kumaran et al. (1996); Shanmuga Sundara Raj et al. (1997, 1998). For a description of hydrogen-bond motifs, see: Etter et al. (1990).
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXTL (Bruker, 2002) and PLATON (Spek (2003).
C13H11NO | F(000) = 832 |
Mr = 197.23 | Dx = 1.235 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 642 reflections |
a = 19.848 (4) Å | θ = 2.7–24.7° |
b = 5.6435 (12) Å | µ = 0.08 mm−1 |
c = 19.325 (4) Å | T = 293 K |
β = 101.535 (4)° | Prism, light yellow |
V = 2120.9 (8) Å3 | 0.34 × 0.13 × 0.11 mm |
Z = 8 |
Bruker APEX area-detector diffractometer | 2069 independent reflections |
Radiation source: fine-focus sealed tube | 1164 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.040 |
φ and ω scans | θmax = 26.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −24→23 |
Tmin = 0.974, Tmax = 0.991 | k = −6→6 |
5274 measured reflections | l = −14→23 |
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)] = 0.054 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0534P)2 + 0.0616P] where P = (Fo2 + 2Fc2)/3 |
2069 reflections | (Δ/σ)max < 0.001 |
136 parameters | Δρmax = 0.13 e Å−3 |
0 restraints | Δρmin = −0.13 e Å−3 |
44 constraints |
C13H11NO | V = 2120.9 (8) Å3 |
Mr = 197.23 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 19.848 (4) Å | µ = 0.08 mm−1 |
b = 5.6435 (12) Å | T = 293 K |
c = 19.325 (4) Å | 0.34 × 0.13 × 0.11 mm |
β = 101.535 (4)° |
Bruker APEX area-detector diffractometer | 2069 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1164 reflections with I > 2σ(I) |
Tmin = 0.974, Tmax = 0.991 | Rint = 0.040 |
5274 measured reflections |
R[F2 > 2σ(F2)] = 0.054 | 0 restraints |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.13 e Å−3 |
2069 reflections | Δρmin = −0.13 e Å−3 |
136 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 | 0.54821 (8) | 0.1673 (3) | 0.58099 (8) | 0.0776 (5) | |
N1 | 0.41400 (9) | 0.2050 (3) | 0.50060 (9) | 0.0635 (5) | |
H1 | 0.4349 | 0.0847 | 0.4874 | 0.076* | |
C1 | 0.44232 (11) | 0.3625 (4) | 0.55205 (10) | 0.0547 (6) | |
C2 | 0.39177 (12) | 0.5253 (4) | 0.55675 (12) | 0.0673 (7) | |
H2 | 0.3961 | 0.6536 | 0.5875 | 0.081* | |
C3 | 0.33346 (12) | 0.4656 (4) | 0.50787 (13) | 0.0762 (7) | |
H3 | 0.2916 | 0.5456 | 0.4997 | 0.091* | |
C4 | 0.34890 (12) | 0.2665 (4) | 0.47383 (12) | 0.0724 (7) | |
H4 | 0.3191 | 0.1871 | 0.4380 | 0.087* | |
C5 | 0.51165 (12) | 0.3362 (4) | 0.59096 (11) | 0.0586 (6) | |
C6 | 0.53729 (12) | 0.5178 (4) | 0.64459 (11) | 0.0640 (6) | |
H6 | 0.5083 | 0.6427 | 0.6503 | 0.077* | |
C7 | 0.59949 (12) | 0.5118 (4) | 0.68497 (11) | 0.0609 (6) | |
H7 | 0.6274 | 0.3860 | 0.6775 | 0.073* | |
C8 | 0.62940 (11) | 0.6813 (4) | 0.74025 (10) | 0.0564 (6) | |
C9 | 0.69227 (11) | 0.6324 (4) | 0.78395 (11) | 0.0645 (6) | |
H9 | 0.7159 | 0.4953 | 0.7767 | 0.077* | |
C10 | 0.72018 (13) | 0.7842 (5) | 0.83802 (13) | 0.0733 (7) | |
H10 | 0.7622 | 0.7486 | 0.8671 | 0.088* | |
C11 | 0.68593 (15) | 0.9879 (5) | 0.84886 (13) | 0.0780 (8) | |
H11 | 0.7046 | 1.0898 | 0.8855 | 0.094* | |
C12 | 0.62420 (14) | 1.0411 (4) | 0.80554 (13) | 0.0782 (7) | |
H12 | 0.6011 | 1.1794 | 0.8128 | 0.094* | |
C13 | 0.59620 (13) | 0.8898 (4) | 0.75115 (12) | 0.0699 (7) | |
H13 | 0.5547 | 0.9283 | 0.7216 | 0.084* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0839 (12) | 0.0726 (11) | 0.0687 (11) | 0.0236 (9) | −0.0030 (8) | −0.0209 (8) |
N1 | 0.0670 (12) | 0.0654 (12) | 0.0563 (11) | 0.0096 (10) | 0.0076 (9) | −0.0115 (10) |
C1 | 0.0643 (14) | 0.0543 (14) | 0.0453 (12) | 0.0030 (11) | 0.0102 (11) | −0.0051 (11) |
C2 | 0.0730 (15) | 0.0639 (16) | 0.0651 (15) | 0.0084 (13) | 0.0138 (13) | −0.0107 (12) |
C3 | 0.0672 (15) | 0.0833 (18) | 0.0767 (17) | 0.0166 (14) | 0.0114 (14) | −0.0072 (14) |
C4 | 0.0619 (15) | 0.0858 (18) | 0.0661 (15) | 0.0029 (14) | 0.0051 (12) | −0.0102 (14) |
C5 | 0.0749 (16) | 0.0527 (14) | 0.0486 (13) | 0.0075 (12) | 0.0134 (11) | −0.0024 (11) |
C6 | 0.0732 (15) | 0.0575 (15) | 0.0609 (14) | 0.0051 (12) | 0.0123 (12) | −0.0109 (11) |
C7 | 0.0684 (14) | 0.0583 (15) | 0.0579 (14) | 0.0009 (12) | 0.0174 (12) | −0.0049 (11) |
C8 | 0.0646 (14) | 0.0539 (14) | 0.0521 (13) | −0.0081 (12) | 0.0154 (11) | −0.0037 (11) |
C9 | 0.0660 (15) | 0.0655 (15) | 0.0631 (15) | −0.0076 (12) | 0.0157 (12) | −0.0018 (12) |
C10 | 0.0717 (16) | 0.0802 (18) | 0.0669 (16) | −0.0221 (15) | 0.0110 (12) | −0.0012 (14) |
C11 | 0.104 (2) | 0.0711 (19) | 0.0591 (15) | −0.0342 (16) | 0.0157 (15) | −0.0060 (13) |
C12 | 0.108 (2) | 0.0550 (15) | 0.0728 (18) | −0.0107 (15) | 0.0210 (16) | −0.0106 (13) |
C13 | 0.0828 (16) | 0.0579 (14) | 0.0672 (16) | −0.0021 (13) | 0.0105 (13) | −0.0049 (12) |
O1—C5 | 1.236 (2) | C7—C8 | 1.468 (3) |
N1—C4 | 1.338 (3) | C7—H7 | 0.9300 |
N1—C1 | 1.368 (2) | C8—C13 | 1.385 (3) |
N1—H1 | 0.8600 | C8—C9 | 1.387 (3) |
C1—C2 | 1.377 (3) | C9—C10 | 1.379 (3) |
C1—C5 | 1.438 (3) | C9—H9 | 0.9300 |
C2—C3 | 1.381 (3) | C10—C11 | 1.373 (3) |
C2—H2 | 0.9300 | C10—H10 | 0.9300 |
C3—C4 | 1.367 (3) | C11—C12 | 1.372 (3) |
C3—H3 | 0.9300 | C11—H11 | 0.9300 |
C4—H4 | 0.9300 | C12—C13 | 1.382 (3) |
C5—C6 | 1.474 (3) | C12—H12 | 0.9300 |
C6—C7 | 1.322 (3) | C13—H13 | 0.9300 |
C6—H6 | 0.9300 | ||
C4—N1—C1 | 109.70 (18) | C6—C7—C8 | 127.4 (2) |
C4—N1—H1 | 125.2 | C6—C7—H7 | 116.3 |
C1—N1—H1 | 125.2 | C8—C7—H7 | 116.3 |
N1—C1—C2 | 106.42 (18) | C13—C8—C9 | 118.3 (2) |
N1—C1—C5 | 121.59 (19) | C13—C8—C7 | 121.9 (2) |
C2—C1—C5 | 132.0 (2) | C9—C8—C7 | 119.8 (2) |
C1—C2—C3 | 108.3 (2) | C10—C9—C8 | 120.9 (2) |
C1—C2—H2 | 125.8 | C10—C9—H9 | 119.5 |
C3—C2—H2 | 125.8 | C8—C9—H9 | 119.5 |
C4—C3—C2 | 107.0 (2) | C11—C10—C9 | 120.0 (2) |
C4—C3—H3 | 126.5 | C11—C10—H10 | 120.0 |
C2—C3—H3 | 126.5 | C9—C10—H10 | 120.0 |
N1—C4—C3 | 108.6 (2) | C12—C11—C10 | 119.9 (2) |
N1—C4—H4 | 125.7 | C12—C11—H11 | 120.0 |
C3—C4—H4 | 125.7 | C10—C11—H11 | 120.0 |
O1—C5—C1 | 121.92 (19) | C11—C12—C13 | 120.2 (3) |
O1—C5—C6 | 121.0 (2) | C11—C12—H12 | 119.9 |
C1—C5—C6 | 117.1 (2) | C13—C12—H12 | 119.9 |
C7—C6—C5 | 123.2 (2) | C12—C13—C8 | 120.6 (2) |
C7—C6—H6 | 118.4 | C12—C13—H13 | 119.7 |
C5—C6—H6 | 118.4 | C8—C13—H13 | 119.7 |
C4—N1—C1—C2 | 0.4 (2) | C1—C5—C6—C7 | 178.6 (2) |
C4—N1—C1—C5 | 178.7 (2) | C5—C6—C7—C8 | −179.1 (2) |
N1—C1—C2—C3 | −0.3 (3) | C6—C7—C8—C13 | −7.4 (3) |
C5—C1—C2—C3 | −178.3 (2) | C6—C7—C8—C9 | 171.7 (2) |
C1—C2—C3—C4 | 0.1 (3) | C13—C8—C9—C10 | 1.6 (3) |
C1—N1—C4—C3 | −0.3 (3) | C7—C8—C9—C10 | −177.45 (19) |
C2—C3—C4—N1 | 0.2 (3) | C8—C9—C10—C11 | −0.5 (3) |
N1—C1—C5—O1 | −1.8 (3) | C9—C10—C11—C12 | −0.5 (4) |
C2—C1—C5—O1 | 175.9 (2) | C10—C11—C12—C13 | 0.2 (4) |
N1—C1—C5—C6 | 179.22 (18) | C11—C12—C13—C8 | 1.0 (4) |
C2—C1—C5—C6 | −3.0 (4) | C9—C8—C13—C12 | −1.9 (3) |
O1—C5—C6—C7 | −0.4 (3) | C7—C8—C13—C12 | 177.2 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.86 | 2.02 | 2.817 (2) | 155 |
C7—H7···O1 | 0.93 | 2.51 | 2.835 (3) | 101 |
Symmetry code: (i) −x+1, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C13H11NO |
Mr | 197.23 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 293 |
a, b, c (Å) | 19.848 (4), 5.6435 (12), 19.325 (4) |
β (°) | 101.535 (4) |
V (Å3) | 2120.9 (8) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.34 × 0.13 × 0.11 |
Data collection | |
Diffractometer | Bruker APEX area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.974, 0.991 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5274, 2069, 1164 |
Rint | 0.040 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.137, 1.00 |
No. of reflections | 2069 |
No. of parameters | 136 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.13, −0.13 |
Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2002) and PLATON (Spek (2003).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.86 | 2.02 | 2.817 (2) | 154.7 |
C7—H7···O1 | 0.93 | 2.51 | 2.835 (3) | 100.7 |
Symmetry code: (i) −x+1, −y, −z+1. |
Chalcone derivatives possess wide variety of pharmaceutical properties, such as anticancer, antibacterial, antiviral, antiprotozoal, insecticidal and enzyme-inhibitory ones (Dimmock et al., 1999; Go et al., 2005; Opletalova, 2000). Some of the substituted chalcones are also reported to possess antileishmanial (Chen et al., 1999), antitubercular (Lin et al., 2002), trypanocidal (Lunardi et al., 2003) activities. As a part of our ongoing efforts in the chalcone compounds (Gong & Shen, 2007), the title compound is reported here for the first time.
In the title compound, C13H11NO, the bond lengths and angles are usual. The –NH groups are involved as donors to form centrosymmetric dimers with a motif R22(10) through N—H···O hydrogen bonds (Etter et al., 1990) - (Fig. 2). There is a pyrrole-H···π-phenyl-ring interaction as indicate the geometric parameters C2—H2···Centroid(phenyl) (1 - x, y, 3/2 - z) where the distance H···centroid and C2···centroid equal to 2.90 and 3.666 (3) Å, respectively, and the angle C2—H2···Centroid(phenyl) equals to 141° (Spek, 2003).