organic compounds
(4Z)-2-Phenyl-1-{(E)-[4-(propan-2-yl)benzylidene]amino}-4-[(thiophen-2-yl)methylidene]-1H-imidazol-5(4H)-one
aSchool of Physics, Shri Mata Vaishno Devi University, Katra 182 320, J&K, India, bDepartment of Chemistry, Mangalore University, Mangalagangothri 574 199, D.K., Mangalore, India, cDepartment of Industrial Chemistry, Mangalore University, Mangalagangothri 574 199, D.K., Mangalore, India, and dX-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India
*Correspondence e-mail: rkant.ju@gmail.com
In the title molecule, C24H21N3OS, the imidazole ring subtends dihedral angles of 4.6 (1) and 20.2 (1)° with the thiophene and iso-propylbenzene rings, respectively. The plane of the imidazole ring forms a dihedral angle of 39.9 (1)° with the phenyl ring. An intramolecular C—H⋯N hydrogen bond closes an S(6) ring. In the crystal, pairs of C—H⋯O hydrogen bonds link molecules into inversion dimers featuring R22(10) graph-set motifs. Aromatic π–π stacking interactions are observed between the thiophene and imidazole rings [centroid–centroid distance = 3.570 (2) Å] and thiophene and benzene rings [centroid–centroid distance = 3.889 (2) Å]. Weak C—H⋯π interactions are also observed.
Keywords: crystal structure; imidazole; hydrogen bonding; π-π interactions.
CCDC reference: 1472955
Structure description
Imidazolones are nitrogen analogues of et al. 2008; Patel et al. 2006), anti-oxidant (Suhasini et al.2014) and anticonvulsant activity (Mohamed et al. 2012).
bearing an exocyclic double bond at the fourth position, usually called unsaturated 2,4-disubstituted 2-imidazolin-5-ones. Compounds containing imidazolone as well as imine moieties exhibit a range of pharmaceutical activities, such as antimicrobial (SuthakaranIn the title compound (Fig. 1), the imidazole ring subtends dihedral angles of 4.6 (1) and 20.2 (1)° with the thiophene and benzene rings, respectively. The dihedral angle between the phenyl and imidazole rings is 39.9 (1)°. The sum of bond angles around N2 is 358.3°, which confirms that the atom N2 is in an sp2 hybridized state. The C7=O1 bond distance is 1.218 (5) Å which is somewhat longer than the standard value for a carbonyl group (1.192 Å); the lengthening of this double bond may be due to the involvement of this oxygen atom as a hydrogen-bond acceptor.
In the crystal, centrosymmetric dimeric aggregates (Fig. 2) are formed by pairs of C—H⋯O hydrogen bonds (Table 1), forming R22(10) ring motifs. π–π interactions are observed between the thiophene and imidazole rings [centroid separation = 3.570 (2) Å, interplanar spacing = 3.528 Å and centroid shift = 0.55 Å] and the thiophene and benzene rings [centroid separation= 3.889 (2) Å, interplanar spacing = 2.976 Å and centroid shift = 2.50 Å]. Weak C—H⋯π interactions are also observed.
Synthesis and crystallization
A mixture of 3-hydrazinyl-3-oxo-1-(thiophen-2-yl)prop-1-en-2-yl]benzamide (0.01 mol) in 2-propanol (30 ml) with 4-(propan-2-yl)benzaldehyde (0.01 mol) in the presence of one or two drops of sulfuric acid was heated under reflux for 8 h. The reaction mixture was then cooled to room temperature and poured on cold water; the solid mass obtained was collected by filtration, washed with cold water and recrystallized at room temperature from a mixture of methanol and N,N-dimethyl formamide (1:1 v/v) giving yellow block-like crystals [m.p. 449 K]
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1472955
10.1107/S2414314616005873/hb4035sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616005873/hb4035Isup2.hkl
A mixture of 3-hydrazinyl-3-oxo-1-(thiophen-2-yl)prop-1-en-2-yl]benzamide (0.01 mol) in 2-propanol (30 ml) with 4-(propan-2-yl)benzaldehyde (0.01 mol) in the presence of one or two drops of sulfuric acid was heated under reflux for 8 h. The reaction mixture was then cooled to room temperature and poured on cold water; the solid mass obtained was collected by filtration, washed with cold water and recrystallized at room temperature from a mixture of methanol and N,N-dimethyl formamide (1:1 v/v) in the form of yellow blocks [m.p. 449 K]
Crystal data, data collection and structure
details are summarized in Table 2. A l l H atoms were positioned geometrically and were treated as riding on their parent C atoms, with C—H distances of 0.93–0.96 A; and with Uiso(H) = 1.2Ueq(C), except for the methyl groups where Uiso(H) = 1.5Ueq(C).Imidazolones are nitrogen analogues of
bearing an exocyclic double bond at the fourth position, usually called unsaturated 2,4-disubstituted 2-imidazolin-5-ones. Compounds containing imidazolone as well as imine moieties exhibit a range of pharmaceutical activities, such as antimicrobial (Suthakaran et al. 2008; Patel et al. 2006), anti-oxidant (Suhasini et al.2014) and anticonvulsant activity (Mohamed et al. 2012).In the title compound (Fig. 1), the imidazole ring subtends dihedral angles of 4.6 (1) and 20.2 (1)° with the thiophene and benzene rings, respectively. The dihedral angle between the phenyl and imidazole rings is 39.9 (1)°. The sum of bond angles around N2 is 358.3°, which confirms that the atom N2 is in an sp2 hybridized state. The C7═O1 bond distance is 1.218 (5) Å which is somewhat longer than the standard value for a carbonyl group (1.192 Å); the lengthening of this double bond may be due to the involvement of this oxygen atom as a hydrogen-bond acceptor.
In the crystal, centrosymmetric dimeric aggregates (Fig. 2) are formed by pairs of C—H···O hydrogen bonds (Table 1), forming R22(10) ring motifs. π–π interactions are observed between the thiophene and imidazole rings [centroid separation = 3.570 (2) Å, = 3.528 Å and centroid shift = 0.55 Å] and the thiophene and benzene rings [centroid separation= 3.889 (2) Å, = 2.976 Å and centroid shift = 2.50 Å]. Weak C—H···π interactions are also observed.
Data collection: CrysAlis PRO (Oxford Diffraction,2010); cell
CrysAlis PRO (Oxford Diffraction,2010); data reduction: CrysAlis PRO (Oxford Diffraction,2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).Fig. 1. ORTEP view of the title molecule with displacement ellipsoids drawn at the 40% probability level. Dashed lines indicate the intramolecular hydrogen bond. | |
Fig. 2. A dimer of molecules of the title compound linked by a pair of C—H···O hydrogen bonds forming an R22(10) loop. |
C24H21N3OS | F(000) = 840 |
Mr = 399.50 | Dx = 1.283 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1816 reflections |
a = 15.8392 (13) Å | θ = 4.1–25.6° |
b = 12.9075 (10) Å | µ = 0.18 mm−1 |
c = 10.3997 (8) Å | T = 293 K |
β = 103.354 (8)° | Block, yellow |
V = 2068.7 (3) Å3 | 0.30 × 0.20 × 0.20 mm |
Z = 4 |
Oxford Diffraction Xcalibur, Sapphire3 diffractometer | 4053 independent reflections |
Radiation source: fine-focus sealed tube | 2412 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
Detector resolution: 16.1049 pixels mm-1 | θmax = 26.0°, θmin = 3.4° |
ω scans | h = −19→19 |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 | k = −15→15 |
Tmin = 0.636, Tmax = 1.000 | l = −10→12 |
8085 measured reflections |
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)] = 0.074 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.247 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.1066P)2 + 1.5103P] where P = (Fo2 + 2Fc2)/3 |
4053 reflections | (Δ/σ)max = 0.001 |
264 parameters | Δρmax = 0.43 e Å−3 |
0 restraints | Δρmin = −0.34 e Å−3 |
C24H21N3OS | V = 2068.7 (3) Å3 |
Mr = 399.50 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 15.8392 (13) Å | µ = 0.18 mm−1 |
b = 12.9075 (10) Å | T = 293 K |
c = 10.3997 (8) Å | 0.30 × 0.20 × 0.20 mm |
β = 103.354 (8)° |
Oxford Diffraction Xcalibur, Sapphire3 diffractometer | 4053 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 | 2412 reflections with I > 2σ(I) |
Tmin = 0.636, Tmax = 1.000 | Rint = 0.033 |
8085 measured reflections |
R[F2 > 2σ(F2)] = 0.074 | 0 restraints |
wR(F2) = 0.247 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.43 e Å−3 |
4053 reflections | Δρmin = −0.34 e Å−3 |
264 parameters |
Experimental. CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.48932 (8) | 0.61536 (9) | 0.93165 (13) | 0.0810 (5) | |
N3 | 0.2515 (2) | 0.9237 (3) | 1.1960 (3) | 0.0596 (8) | |
N1 | 0.37039 (19) | 0.7338 (2) | 1.0619 (3) | 0.0565 (8) | |
N2 | 0.31414 (19) | 0.8713 (2) | 1.1460 (3) | 0.0586 (8) | |
O1 | 0.3822 (2) | 1.0076 (2) | 1.0621 (3) | 0.0852 (10) | |
C9 | 0.2618 (2) | 0.6909 (3) | 1.1846 (4) | 0.0521 (9) | |
C17 | 0.1300 (3) | 1.0434 (3) | 1.2985 (4) | 0.0661 (11) | |
H17 | 0.1079 | 0.9851 | 1.2497 | 0.079* | |
C8 | 0.3151 (2) | 0.7636 (3) | 1.1301 (4) | 0.0535 (9) | |
C5 | 0.4681 (2) | 0.8271 (3) | 0.9533 (4) | 0.0639 (10) | |
H5 | 0.4867 | 0.8930 | 0.9363 | 0.077* | |
C16 | 0.2157 (2) | 1.0712 (3) | 1.3090 (4) | 0.0557 (9) | |
C6 | 0.4073 (2) | 0.8230 (3) | 1.0243 (4) | 0.0601 (10) | |
C14 | 0.2251 (3) | 0.7125 (3) | 1.2905 (4) | 0.0634 (10) | |
H14 | 0.2293 | 0.7789 | 1.3263 | 0.076* | |
C4 | 0.5077 (2) | 0.7429 (3) | 0.9007 (4) | 0.0602 (10) | |
C15 | 0.2759 (3) | 1.0096 (3) | 1.2529 (4) | 0.0606 (10) | |
H15 | 0.3322 | 1.0331 | 1.2588 | 0.073* | |
C19 | 0.1081 (3) | 1.1886 (4) | 1.4336 (5) | 0.0773 (13) | |
C7 | 0.3709 (3) | 0.9153 (3) | 1.0755 (4) | 0.0646 (11) | |
C13 | 0.1821 (3) | 0.6353 (4) | 1.3432 (4) | 0.0736 (12) | |
H13 | 0.1591 | 0.6496 | 1.4158 | 0.088* | |
C10 | 0.2515 (3) | 0.5916 (3) | 1.1311 (5) | 0.0702 (12) | |
H10 | 0.2744 | 0.5763 | 1.0587 | 0.084* | |
C21 | 0.2456 (3) | 1.1606 (3) | 1.3806 (4) | 0.0687 (11) | |
H21 | 0.3025 | 1.1822 | 1.3874 | 0.082* | |
C18 | 0.0771 (3) | 1.1004 (4) | 1.3589 (5) | 0.0765 (13) | |
H18 | 0.0197 | 1.0802 | 1.3502 | 0.092* | |
C3 | 0.5704 (3) | 0.7537 (3) | 0.8164 (4) | 0.0612 (10) | |
H3 | 0.5913 | 0.8153 | 0.7894 | 0.073* | |
C20 | 0.1924 (3) | 1.2173 (3) | 1.4413 (5) | 0.0796 (14) | |
H20 | 0.2140 | 1.2765 | 1.4886 | 0.096* | |
C1 | 0.5561 (3) | 0.5752 (4) | 0.8383 (5) | 0.0809 (13) | |
H1 | 0.5669 | 0.5056 | 0.8249 | 0.097* | |
C11 | 0.2084 (3) | 0.5161 (4) | 1.1823 (5) | 0.0862 (15) | |
H11 | 0.2028 | 0.4501 | 1.1455 | 0.103* | |
C2 | 0.5925 (3) | 0.6525 (4) | 0.7848 (5) | 0.0877 (15) | |
H2 | 0.6302 | 0.6403 | 0.7300 | 0.105* | |
C22 | 0.0515 (4) | 1.2478 (4) | 1.5091 (7) | 0.112 (2) | |
H22 | 0.0963 | 1.2742 | 1.5832 | 0.135* | |
C12 | 0.1736 (3) | 0.5381 (4) | 1.2884 (5) | 0.0834 (14) | |
H12 | 0.1441 | 0.4870 | 1.3233 | 0.100* | |
C23 | 0.0029 (5) | 1.1847 (5) | 1.5790 (6) | 0.137 (3) | |
H23A | −0.0227 | 1.2276 | 1.6352 | 0.206* | |
H23B | 0.0408 | 1.1350 | 1.6318 | 0.206* | |
H23C | −0.0421 | 1.1492 | 1.5169 | 0.206* | |
C24 | 0.0168 (5) | 1.3427 (5) | 1.4508 (7) | 0.138 (3) | |
H24A | −0.0288 | 1.3286 | 1.3744 | 0.207* | |
H24B | 0.0617 | 1.3818 | 1.4251 | 0.207* | |
H24C | −0.0060 | 1.3818 | 1.5136 | 0.207* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0782 (8) | 0.0620 (8) | 0.1081 (10) | −0.0024 (6) | 0.0322 (7) | −0.0085 (6) |
N3 | 0.0539 (18) | 0.0530 (19) | 0.076 (2) | 0.0012 (15) | 0.0237 (16) | −0.0084 (16) |
N1 | 0.0487 (17) | 0.0492 (18) | 0.074 (2) | −0.0024 (14) | 0.0204 (16) | −0.0050 (16) |
N2 | 0.0534 (18) | 0.0491 (19) | 0.079 (2) | −0.0051 (14) | 0.0273 (16) | −0.0111 (16) |
O1 | 0.085 (2) | 0.0509 (19) | 0.135 (3) | −0.0133 (15) | 0.056 (2) | −0.0143 (18) |
C9 | 0.0396 (18) | 0.053 (2) | 0.062 (2) | −0.0018 (16) | 0.0080 (16) | −0.0053 (18) |
C17 | 0.060 (2) | 0.055 (2) | 0.085 (3) | −0.0010 (19) | 0.020 (2) | −0.009 (2) |
C8 | 0.0459 (19) | 0.051 (2) | 0.063 (2) | −0.0013 (16) | 0.0104 (17) | −0.0071 (18) |
C5 | 0.056 (2) | 0.054 (2) | 0.085 (3) | −0.0081 (18) | 0.025 (2) | −0.007 (2) |
C16 | 0.057 (2) | 0.048 (2) | 0.065 (2) | 0.0024 (17) | 0.0205 (18) | 0.0003 (18) |
C6 | 0.048 (2) | 0.057 (2) | 0.077 (3) | −0.0055 (18) | 0.0181 (19) | −0.010 (2) |
C14 | 0.066 (2) | 0.057 (2) | 0.069 (2) | 0.0005 (19) | 0.019 (2) | −0.0049 (19) |
C4 | 0.054 (2) | 0.057 (2) | 0.071 (2) | −0.0005 (18) | 0.0173 (19) | −0.002 (2) |
C15 | 0.055 (2) | 0.052 (2) | 0.080 (3) | −0.0061 (18) | 0.025 (2) | −0.009 (2) |
C19 | 0.089 (3) | 0.057 (3) | 0.099 (3) | 0.016 (2) | 0.049 (3) | 0.010 (2) |
C7 | 0.056 (2) | 0.054 (3) | 0.087 (3) | −0.0052 (18) | 0.024 (2) | −0.009 (2) |
C13 | 0.064 (3) | 0.082 (3) | 0.081 (3) | 0.002 (2) | 0.029 (2) | 0.009 (3) |
C10 | 0.065 (3) | 0.060 (3) | 0.089 (3) | −0.007 (2) | 0.025 (2) | −0.014 (2) |
C21 | 0.068 (3) | 0.055 (2) | 0.089 (3) | −0.008 (2) | 0.031 (2) | −0.009 (2) |
C18 | 0.057 (2) | 0.072 (3) | 0.107 (3) | 0.005 (2) | 0.033 (2) | 0.004 (3) |
C3 | 0.068 (2) | 0.048 (2) | 0.073 (2) | 0.0073 (19) | 0.026 (2) | −0.0071 (19) |
C20 | 0.099 (4) | 0.052 (3) | 0.101 (3) | 0.000 (2) | 0.050 (3) | −0.010 (2) |
C1 | 0.087 (3) | 0.067 (3) | 0.093 (3) | 0.008 (3) | 0.027 (3) | −0.017 (3) |
C11 | 0.085 (3) | 0.056 (3) | 0.126 (4) | −0.017 (2) | 0.044 (3) | −0.012 (3) |
C2 | 0.085 (3) | 0.101 (4) | 0.085 (3) | 0.005 (3) | 0.037 (3) | 0.000 (3) |
C22 | 0.131 (5) | 0.075 (4) | 0.160 (5) | 0.017 (3) | 0.094 (5) | 0.000 (4) |
C12 | 0.068 (3) | 0.072 (3) | 0.115 (4) | −0.011 (2) | 0.031 (3) | 0.014 (3) |
C23 | 0.188 (7) | 0.120 (5) | 0.145 (5) | 0.066 (5) | 0.123 (5) | 0.049 (4) |
C24 | 0.196 (7) | 0.094 (4) | 0.164 (6) | 0.077 (5) | 0.126 (6) | 0.050 (4) |
S1—C1 | 1.675 (5) | C19—C22 | 1.526 (6) |
S1—C4 | 1.715 (4) | C13—C12 | 1.372 (7) |
N3—C15 | 1.274 (5) | C13—H13 | 0.9300 |
N3—N2 | 1.397 (4) | C10—C11 | 1.366 (6) |
N1—C8 | 1.306 (4) | C10—H10 | 0.9300 |
N1—C6 | 1.388 (5) | C21—C20 | 1.376 (6) |
N2—C8 | 1.400 (5) | C21—H21 | 0.9300 |
N2—C7 | 1.405 (5) | C18—H18 | 0.9300 |
O1—C7 | 1.218 (5) | C3—C2 | 1.410 (6) |
C9—C14 | 1.387 (5) | C3—H3 | 0.9300 |
C9—C10 | 1.392 (5) | C20—H20 | 0.9300 |
C9—C8 | 1.461 (5) | C1—C2 | 1.336 (7) |
C17—C18 | 1.372 (6) | C1—H1 | 0.9300 |
C17—C16 | 1.384 (5) | C11—C12 | 1.372 (7) |
C17—H17 | 0.9300 | C11—H11 | 0.9300 |
C5—C6 | 1.343 (5) | C2—H2 | 0.9300 |
C5—C4 | 1.426 (6) | C22—C24 | 1.419 (7) |
C5—H5 | 0.9300 | C22—C23 | 1.429 (7) |
C16—C21 | 1.395 (5) | C22—H22 | 0.9800 |
C16—C15 | 1.463 (5) | C12—H12 | 0.9300 |
C6—C7 | 1.476 (6) | C23—H23A | 0.9600 |
C14—C13 | 1.389 (6) | C23—H23B | 0.9600 |
C14—H14 | 0.9300 | C23—H23C | 0.9600 |
C4—C3 | 1.474 (5) | C24—H24A | 0.9600 |
C15—H15 | 0.9300 | C24—H24B | 0.9600 |
C19—C20 | 1.369 (6) | C24—H24C | 0.9600 |
C19—C18 | 1.402 (6) | ||
C1—S1—C4 | 91.8 (2) | C9—C10—H10 | 119.2 |
C15—N3—N2 | 115.4 (3) | C20—C21—C16 | 121.1 (4) |
C8—N1—C6 | 106.8 (3) | C20—C21—H21 | 119.5 |
N3—N2—C8 | 123.5 (3) | C16—C21—H21 | 119.5 |
N3—N2—C7 | 126.4 (3) | C17—C18—C19 | 121.1 (4) |
C8—N2—C7 | 108.4 (3) | C17—C18—H18 | 119.4 |
C14—C9—C10 | 118.1 (4) | C19—C18—H18 | 119.4 |
C14—C9—C8 | 124.3 (4) | C2—C3—C4 | 106.8 (4) |
C10—C9—C8 | 117.5 (3) | C2—C3—H3 | 126.6 |
C18—C17—C16 | 121.1 (4) | C4—C3—H3 | 126.6 |
C18—C17—H17 | 119.5 | C19—C20—C21 | 121.4 (4) |
C16—C17—H17 | 119.5 | C19—C20—H20 | 119.3 |
N1—C8—N2 | 112.5 (3) | C21—C20—H20 | 119.3 |
N1—C8—C9 | 122.8 (3) | C2—C1—S1 | 113.6 (4) |
N2—C8—C9 | 124.7 (3) | C2—C1—H1 | 123.2 |
C6—C5—C4 | 128.0 (4) | S1—C1—H1 | 123.2 |
C6—C5—H5 | 116.0 | C10—C11—C12 | 119.7 (5) |
C4—C5—H5 | 116.0 | C10—C11—H11 | 120.2 |
C17—C16—C21 | 117.6 (3) | C12—C11—H11 | 120.2 |
C17—C16—C15 | 123.0 (4) | C1—C2—C3 | 116.1 (4) |
C21—C16—C15 | 119.4 (3) | C1—C2—H2 | 121.9 |
C5—C6—N1 | 126.2 (4) | C3—C2—H2 | 121.9 |
C5—C6—C7 | 123.8 (4) | C24—C22—C23 | 120.5 (5) |
N1—C6—C7 | 110.0 (3) | C24—C22—C19 | 115.4 (5) |
C9—C14—C13 | 120.1 (4) | C23—C22—C19 | 115.2 (5) |
C9—C14—H14 | 119.9 | C24—C22—H22 | 100.1 |
C13—C14—H14 | 119.9 | C23—C22—H22 | 100.1 |
C5—C4—C3 | 124.9 (4) | C19—C22—H22 | 100.1 |
C5—C4—S1 | 123.4 (3) | C13—C12—C11 | 120.3 (4) |
C3—C4—S1 | 111.6 (3) | C13—C12—H12 | 119.9 |
N3—C15—C16 | 120.2 (3) | C11—C12—H12 | 119.9 |
N3—C15—H15 | 119.9 | C22—C23—H23A | 109.5 |
C16—C15—H15 | 119.9 | C22—C23—H23B | 109.5 |
C20—C19—C18 | 117.7 (4) | H23A—C23—H23B | 109.5 |
C20—C19—C22 | 121.0 (5) | C22—C23—H23C | 109.5 |
C18—C19—C22 | 121.3 (5) | H23A—C23—H23C | 109.5 |
O1—C7—N2 | 125.8 (4) | H23B—C23—H23C | 109.5 |
O1—C7—C6 | 132.0 (4) | C22—C24—H24A | 109.5 |
N2—C7—C6 | 102.2 (3) | C22—C24—H24B | 109.5 |
C12—C13—C14 | 120.2 (4) | H24A—C24—H24B | 109.5 |
C12—C13—H13 | 119.9 | C22—C24—H24C | 109.5 |
C14—C13—H13 | 119.9 | H24A—C24—H24C | 109.5 |
C11—C10—C9 | 121.6 (4) | H24B—C24—H24C | 109.5 |
C11—C10—H10 | 119.2 | ||
C15—N3—N2—C8 | 153.1 (4) | N3—N2—C7—C6 | −168.3 (3) |
C15—N3—N2—C7 | −43.6 (5) | C8—N2—C7—C6 | −2.9 (4) |
C6—N1—C8—N2 | −2.2 (4) | C5—C6—C7—O1 | 3.8 (8) |
C6—N1—C8—C9 | 178.7 (3) | N1—C6—C7—O1 | −176.9 (5) |
N3—N2—C8—N1 | 169.3 (3) | C5—C6—C7—N2 | −177.6 (4) |
C7—N2—C8—N1 | 3.4 (4) | N1—C6—C7—N2 | 1.7 (4) |
N3—N2—C8—C9 | −11.6 (6) | C9—C14—C13—C12 | −1.9 (6) |
C7—N2—C8—C9 | −177.6 (4) | C14—C9—C10—C11 | −1.6 (6) |
C14—C9—C8—N1 | 157.6 (4) | C8—C9—C10—C11 | 174.9 (4) |
C10—C9—C8—N1 | −18.7 (5) | C17—C16—C21—C20 | 1.6 (6) |
C14—C9—C8—N2 | −21.4 (6) | C15—C16—C21—C20 | −176.2 (4) |
C10—C9—C8—N2 | 162.3 (4) | C16—C17—C18—C19 | −0.2 (7) |
C18—C17—C16—C21 | −1.5 (6) | C20—C19—C18—C17 | 1.7 (7) |
C18—C17—C16—C15 | 176.3 (4) | C22—C19—C18—C17 | −175.6 (5) |
C4—C5—C6—N1 | 0.3 (7) | C5—C4—C3—C2 | −179.2 (4) |
C4—C5—C6—C7 | 179.4 (4) | S1—C4—C3—C2 | 2.1 (4) |
C8—N1—C6—C5 | 179.5 (4) | C18—C19—C20—C21 | −1.5 (7) |
C8—N1—C6—C7 | 0.3 (4) | C22—C19—C20—C21 | 175.8 (5) |
C10—C9—C14—C13 | 2.2 (6) | C16—C21—C20—C19 | −0.2 (7) |
C8—C9—C14—C13 | −174.1 (4) | C4—S1—C1—C2 | 0.4 (4) |
C6—C5—C4—C3 | 176.0 (4) | C9—C10—C11—C12 | 0.6 (7) |
C6—C5—C4—S1 | −5.4 (6) | S1—C1—C2—C3 | 0.9 (6) |
C1—S1—C4—C5 | 179.8 (4) | C4—C3—C2—C1 | −1.9 (6) |
C1—S1—C4—C3 | −1.4 (3) | C20—C19—C22—C24 | 78.6 (8) |
N2—N3—C15—C16 | 180.0 (3) | C18—C19—C22—C24 | −104.2 (7) |
C17—C16—C15—N3 | −3.1 (6) | C20—C19—C22—C23 | −133.9 (6) |
C21—C16—C15—N3 | 174.6 (4) | C18—C19—C22—C23 | 43.3 (8) |
N3—N2—C7—O1 | 10.4 (7) | C14—C13—C12—C11 | 0.9 (7) |
C8—N2—C7—O1 | 175.8 (4) | C10—C11—C12—C13 | −0.2 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14···N3 | 0.93 | 2.38 | 2.960 (5) | 120 |
C5—H5···O1i | 0.93 | 2.44 | 3.221 (5) | 142 |
C3—H3···O1i | 0.93 | 2.74 | 3.349 (5) | 124 |
Symmetry code: (i) −x+1, −y+2, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14···N3 | 0.93 | 2.38 | 2.960 (5) | 120 |
C5—H5···O1i | 0.93 | 2.44 | 3.221 (5) | 142 |
C3—H3···O1i | 0.93 | 2.74 | 3.349 (5) | 124 |
Symmetry code: (i) −x+1, −y+2, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C24H21N3OS |
Mr | 399.50 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 15.8392 (13), 12.9075 (10), 10.3997 (8) |
β (°) | 103.354 (8) |
V (Å3) | 2068.7 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.18 |
Crystal size (mm) | 0.30 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur, Sapphire3 |
Absorption correction | Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 |
Tmin, Tmax | 0.636, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8085, 4053, 2412 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.074, 0.247, 1.05 |
No. of reflections | 4053 |
No. of parameters | 264 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.43, −0.34 |
Computer programs: CrysAlis PRO (Oxford Diffraction,2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), PLATON (Spek, 2009).
Acknowledgements
RK acknowledges the Indian Council of Medical Research, New Delhi, for financial support under Research Project No. BIC/12 (14)/2012. K is thankful to the UGC for funding under Project No. MRP-MAJOR-PHYS-2013–26952 (RP-88). SNK acknowledges the Department of Chemistry, ShriMadhwaVadiraja Institute of Technology, Bantakal (VTU Belgam), for providing research facilities.
References
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Mohamed, M. S., Mahmoud, R. K., Sayad, A. I. & El-Araby, M. E. (2012). J. Med. Chem. 2, 24–29. CAS Google Scholar
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Patel, A., Bari, S., Talele, G., Patel, J. & Sarangapani, M. (2006). Iran. J. Pharm. Res. 4, 249–254. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Suhasini, G. E., Nirmala, M., Varalakshmi, Giri, A., Solomon, B. & Sahitha, G. (2014). Int. J. Pharm. 4, 241–246. Google Scholar
Suthakaran, R., Kavimani, S., Venkaiaiah, P. & Suganthi, K. (2008). Rasayan J. Chem. 1, 22–29. CAS Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Imidazolones are nitrogen analogues of azlactones bearing an exocyclic double bond at the fourth position usually called unsaturated 2,4-disubtituted 2-imidazolin-5-ones. Compounds containing imidazolone as well as imine moieties exhibit a range of pharmaceutical activities, such as antimicrobial (Suthakaran et al. 2008 & Patel et al. 2006), antioxidant (Suhasini et al.2014) and anticonvulsant activity (Mohamed et al. 2012).
In the title compound, the imidazole ring subtends dihedral angles of 4.6 (1) and 20.2 (1)° with the thiophene and benzene rings, respectively. The dihedral angle between the phenyl ring and imidazole ring is 39.9 (1)°. The sum of bond angles around N2 is 360° which confirms that the atom N2 is in sp2 hybridized state. The C7=O1 bond distance is 1.218 (5)Å which is somewhat longer than the standard value for carbonyl group [1.192Å] and lengthening of this double bond may be due to the involvement of this oxygen atom as a hydrogen-bond acceptor. In the crystal, centrosymmetric dimeric aggregates are formed by pairs of C—H···O hydrogen bonds forming R22(10) ring motifs. In the crystal, π-π interactions are observed between the thiophene and imidazole rings [centroid separation = 3.570 (2) Å, interplanar spacing = 3.528 Å and centroid shift = 0.55 Å] and thiophene and benzene rings [Centroid separation= 3.889 (2) Å, interplanar spacing = 2.976 Å and centroid shift = 2.50Å]. Weak C—H···π interactions are also observed.