organic compounds
(4Z)-1-[(E)-(4-Methoxybenzylidene)amino]-2-phenyl-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 compound, C22H17N3O2S, the imidazole ring forms dihedral angles of 9.2 (2), 10.9 (2) and 12.5 (2)° with the thiophene, phenyl and methoxy-substituted benzene rings, respectively. There are two intramolecular C—H⋯N hydrogen bonds forming S(5) and S(6) rings and one intramolecular C—H⋯O hydrogen bond forming an S(6) ring.
Keywords: crystal structure; imidazole; hydrogen bonding.
CCDC reference: 1472471
Structure description
Compounds containing the imidazolone as well as the imine moiety exhibit pharmaceutical activities such as antimicrobial (Suthakaran et al., 2008; Patel et al., 2006), anti-oxidant (Suhasini et al., 2014), anticonvulsant (Mohamed et al., 2012), anthelmintic (Patel et al., 2010) antibacterial (Solankee et al., 2011) analgesic (Sridhar & Ramesh, 2001), anti-inflammatory (Viveka et al., 2015) and antitumor (Hodnett & Dunn, 1970). Apart from their biological activity, have assumed importance as ligands in coordination chemistry (Özkar et al. 2004, Pouralimardan et al., 2007; Patti et al., 2009). Structural information on the title compound is useful in developing the coordination properties of and to investigate new ligands.
The molecular structure of the title compound is shown in Fig. 1. The bond lengths and angles have normal values and all aromatic rings are essentially planar. The imidazole ring forms dihedral angles of 9.2 (2), 10.9 (2) and 12.5 (2)° with the thiophene (S1/C1–C4), phenyl (C9–C14) and methoxy-substituted benzene (C16–C21) rings, respectively. The methoxy group is essentially planar with the benzene ring to which it is attached, with a C22—O2—C19—C18 torsion angle of −0.8 (4)°. There are two intramolecular C—H⋯N hydrogen bonds (Table 1), forming S(5) and S(6) rings, and one intramolecular C—H⋯O hydrogen bond forming an S(6) ring (Fig. 1).
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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-methoxybenzaldehyde (0.01 mol) in presence of one to two drops of sulfuric acid were heated under reflux for 8 h. The reaction mixture was cooled to ambient temperature and poured on cold water. The solid mass obtained was collected by filtration and washed with cold water. It was crystallized at ambient temperature in the presence of air from a mixture of methanol and N,N-dimethylformamide(1:1 v/v) (m.p. 421 K).
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1472471
10.1107/S2414314616005666/lh4005sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Supporting information file. DOI: 10.1107/S2414314616005666/lh4005Isup2.cml
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-methoxybenzaldehyde (0.01 mol) in presence of one to two drops of sulfuric acid were heated under reflux for 8 h. The reaction mixture was cooled to ambient temperature and poured on cold water. The solid mass obtained was collected by filtration and washed with cold water. It was crystallized at ambient temperature in the presence of air from a mixture of methanol and N,N-dimethylformamide(1:1 v/v) (m.p. 421 K).
Compounds containing the imidazolone as well as the imine moiety exhibit pharmaceutical activities such as antimicrobial (Suthakaran et al., 2008; Patel et al., 2006), anti-oxidant (Suhasini et al., 2014), anticonvulsant (Mohamed et al., 2012), anthelmintic (Patel et al., 2010) antibacterial (Solankee et al., 2011) analgesic (Sridhar & Ramesh, 2001), anti-inflammatory (Viveka et al., 2015) and antitumor (Hodnett & Dunn, 1970). Apart from their biological activity,
have assumed importance as ligands in coordination chemistry (Özkar et al. 2004, Pouralimardan et al., 2007; Patti et al., 2009). Structural information on the title compound is useful in developing the coordination properties of and to investigate new ligands.The molecular structure of the title compound is shown in Fig. 1. The bond lengths and angles have normal values and all aromatic rings are essentially planar. The imidazole ring forms dihedral angles of 9.2 (2), 10.9 (2) and 12.5 (2)° with the thiophene (S1/C1–C4), phenyl (C9–C14) and methoxy-substituted benzene (C16–C21) rings, respectively. The methoxy group is essentially planar with the benzene ring to which it is attached, with a C22—O2—C19—C18 torsion angle of -0.8 (4)°. There are two intramolecular C—H···N hydrogen bonds (Table 1), forming S(5) and S(6) rings, and one intramolecular C—H···O hydrogen bond forming an S(6) ring (Fig. 1).
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. The molecular structure of the title compound, with displacement ellipsoids drawn at the 40% probability level. H atoms are shown as small spheres of arbitrary radii. Dashed lines indicate weak intramolecular hydrogen bonds. |
C22H17N3O2S | F(000) = 808 |
Mr = 387.45 | Dx = 1.378 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1894 reflections |
a = 20.6796 (18) Å | θ = 4.2–27.1° |
b = 5.4004 (4) Å | µ = 0.20 mm−1 |
c = 17.2537 (16) Å | T = 293 K |
β = 104.299 (9)° | Rectangular, white |
V = 1867.2 (3) Å3 | 0.30 × 0.20 × 0.20 mm |
Z = 4 |
Oxford Diffraction Xcalibur Sapphire3 diffractometer | 3663 independent reflections |
Radiation source: fine-focus sealed tube | 2215 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
Detector resolution: 16.1049 pixels mm-1 | θmax = 26.0°, θmin = 3.9° |
ω scans | h = −21→25 |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010) | k = −6→4 |
Tmin = 0.769, Tmax = 1.000 | l = −21→15 |
7300 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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.136 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0436P)2 + 0.2269P] where P = (Fo2 + 2Fc2)/3 |
3663 reflections | (Δ/σ)max = 0.001 |
255 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
C22H17N3O2S | V = 1867.2 (3) Å3 |
Mr = 387.45 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 20.6796 (18) Å | µ = 0.20 mm−1 |
b = 5.4004 (4) Å | T = 293 K |
c = 17.2537 (16) Å | 0.30 × 0.20 × 0.20 mm |
β = 104.299 (9)° |
Oxford Diffraction Xcalibur Sapphire3 diffractometer | 3663 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010) | 2215 reflections with I > 2σ(I) |
Tmin = 0.769, Tmax = 1.000 | Rint = 0.028 |
7300 measured reflections |
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.136 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.24 e Å−3 |
3663 reflections | Δρmin = −0.23 e Å−3 |
255 parameters |
Experimental. Absorption correction: 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 | 0.44505 (4) | 0.95712 (13) | 0.26907 (4) | 0.0566 (3) | |
N1 | 0.33090 (10) | 0.8287 (4) | 0.12524 (13) | 0.0476 (6) | |
C9 | 0.28224 (12) | 1.0201 (5) | −0.00327 (15) | 0.0435 (6) | |
N2 | 0.23366 (10) | 0.6575 (4) | 0.05940 (13) | 0.0469 (5) | |
O1 | 0.22389 (9) | 0.3399 (4) | 0.14907 (11) | 0.0633 (6) | |
C7 | 0.25357 (14) | 0.5141 (5) | 0.12958 (16) | 0.0498 (7) | |
C8 | 0.28221 (12) | 0.8389 (5) | 0.06065 (15) | 0.0444 (6) | |
N3 | 0.17324 (11) | 0.6492 (4) | 0.00114 (13) | 0.0518 (6) | |
C10 | 0.33009 (13) | 1.2060 (5) | 0.01438 (17) | 0.0508 (7) | |
H10 | 0.3591 | 1.2132 | 0.0650 | 0.061* | |
C5 | 0.35065 (13) | 0.5749 (5) | 0.24616 (16) | 0.0499 (7) | |
H5 | 0.3359 | 0.4344 | 0.2678 | 0.060* | |
C14 | 0.23988 (13) | 1.0125 (5) | −0.07990 (17) | 0.0539 (7) | |
H14 | 0.2079 | 0.8885 | −0.0930 | 0.065* | |
O2 | −0.11004 (10) | 0.3630 (4) | −0.22410 (13) | 0.0745 (6) | |
C4 | 0.40723 (13) | 0.6972 (5) | 0.29599 (15) | 0.0473 (7) | |
C1 | 0.50041 (14) | 0.9677 (6) | 0.36046 (17) | 0.0613 (8) | |
H1 | 0.5338 | 1.0866 | 0.3749 | 0.074* | |
C13 | 0.24499 (15) | 1.1877 (5) | −0.13666 (17) | 0.0595 (8) | |
H13 | 0.2164 | 1.1812 | −0.1875 | 0.071* | |
C12 | 0.29240 (15) | 1.3713 (5) | −0.11775 (18) | 0.0600 (8) | |
H12 | 0.2957 | 1.4896 | −0.1558 | 0.072* | |
C2 | 0.49050 (14) | 0.7853 (6) | 0.40935 (18) | 0.0618 (8) | |
H2 | 0.5161 | 0.7651 | 0.4614 | 0.074* | |
C6 | 0.31598 (13) | 0.6373 (5) | 0.17177 (16) | 0.0479 (7) | |
C16 | 0.07441 (14) | 0.4331 (5) | −0.06258 (16) | 0.0527 (7) | |
C15 | 0.13843 (14) | 0.4562 (5) | −0.00441 (17) | 0.0601 (8) | |
H15 | 0.1540 | 0.3241 | 0.0297 | 0.072* | |
C19 | −0.04988 (14) | 0.3744 (5) | −0.16912 (17) | 0.0543 (7) | |
C21 | 0.05040 (15) | 0.6050 (5) | −0.12224 (18) | 0.0634 (8) | |
H21 | 0.0762 | 0.7426 | −0.1268 | 0.076* | |
C3 | 0.43762 (14) | 0.6291 (5) | 0.37355 (16) | 0.0555 (7) | |
H3 | 0.4243 | 0.4939 | 0.3992 | 0.067* | |
C11 | 0.33506 (14) | 1.3800 (5) | −0.04245 (18) | 0.0580 (8) | |
H11 | 0.3673 | 1.5035 | −0.0299 | 0.070* | |
C17 | 0.03512 (17) | 0.2308 (6) | −0.0599 (2) | 0.0823 (11) | |
H17 | 0.0507 | 0.1090 | −0.0217 | 0.099* | |
C18 | −0.02719 (16) | 0.2015 (6) | −0.1122 (2) | 0.0762 (10) | |
H18 | −0.0532 | 0.0639 | −0.1081 | 0.091* | |
C20 | −0.01077 (15) | 0.5760 (6) | −0.17477 (19) | 0.0674 (9) | |
H20 | −0.0259 | 0.6935 | −0.2145 | 0.081* | |
C22 | −0.15119 (16) | 0.1525 (6) | −0.2217 (2) | 0.0901 (12) | |
H22A | −0.1300 | 0.0068 | −0.2357 | 0.135* | |
H22B | −0.1937 | 0.1750 | −0.2590 | 0.135* | |
H22C | −0.1576 | 0.1342 | −0.1687 | 0.135* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0543 (5) | 0.0598 (5) | 0.0512 (5) | −0.0039 (4) | 0.0044 (4) | 0.0050 (3) |
N1 | 0.0426 (13) | 0.0533 (13) | 0.0432 (13) | −0.0023 (10) | 0.0038 (11) | 0.0027 (10) |
C9 | 0.0389 (15) | 0.0493 (15) | 0.0421 (15) | 0.0057 (12) | 0.0096 (12) | 0.0014 (12) |
N2 | 0.0385 (12) | 0.0565 (13) | 0.0431 (13) | −0.0050 (11) | 0.0051 (10) | −0.0003 (10) |
O1 | 0.0606 (13) | 0.0725 (13) | 0.0539 (13) | −0.0183 (11) | 0.0089 (11) | 0.0084 (10) |
C7 | 0.0466 (16) | 0.0599 (18) | 0.0420 (16) | −0.0003 (14) | 0.0092 (13) | −0.0004 (13) |
C8 | 0.0377 (14) | 0.0510 (16) | 0.0440 (16) | −0.0024 (13) | 0.0090 (13) | −0.0023 (12) |
N3 | 0.0378 (13) | 0.0688 (15) | 0.0450 (13) | −0.0054 (12) | 0.0032 (11) | −0.0018 (11) |
C10 | 0.0443 (16) | 0.0549 (17) | 0.0515 (17) | −0.0014 (13) | 0.0089 (14) | −0.0028 (13) |
C5 | 0.0461 (16) | 0.0572 (16) | 0.0457 (16) | 0.0024 (13) | 0.0103 (13) | 0.0079 (13) |
C14 | 0.0468 (16) | 0.0619 (18) | 0.0491 (17) | −0.0001 (14) | 0.0042 (14) | 0.0011 (14) |
O2 | 0.0502 (13) | 0.0910 (15) | 0.0701 (15) | −0.0045 (12) | −0.0083 (11) | −0.0081 (12) |
C4 | 0.0437 (15) | 0.0558 (16) | 0.0413 (15) | 0.0073 (13) | 0.0087 (13) | 0.0036 (12) |
C1 | 0.0500 (18) | 0.0685 (19) | 0.0581 (19) | −0.0053 (15) | −0.0002 (15) | −0.0074 (16) |
C13 | 0.0559 (19) | 0.070 (2) | 0.0478 (17) | 0.0097 (16) | 0.0038 (15) | 0.0091 (15) |
C12 | 0.063 (2) | 0.0571 (18) | 0.063 (2) | 0.0128 (16) | 0.0204 (17) | 0.0121 (15) |
C2 | 0.0523 (18) | 0.079 (2) | 0.0469 (17) | 0.0021 (16) | −0.0008 (15) | 0.0030 (16) |
C6 | 0.0422 (15) | 0.0557 (16) | 0.0431 (15) | −0.0012 (13) | 0.0055 (13) | 0.0026 (13) |
C16 | 0.0495 (17) | 0.0588 (17) | 0.0459 (16) | −0.0063 (15) | 0.0045 (14) | −0.0035 (14) |
C15 | 0.0549 (18) | 0.0609 (18) | 0.0566 (19) | −0.0094 (16) | −0.0008 (15) | −0.0005 (15) |
C19 | 0.0455 (16) | 0.0651 (19) | 0.0477 (17) | −0.0018 (15) | 0.0029 (14) | −0.0114 (15) |
C21 | 0.0567 (19) | 0.0653 (19) | 0.063 (2) | −0.0126 (16) | 0.0040 (16) | 0.0053 (16) |
C3 | 0.0524 (17) | 0.0639 (18) | 0.0459 (17) | 0.0007 (15) | 0.0039 (14) | 0.0076 (14) |
C11 | 0.0522 (17) | 0.0547 (17) | 0.067 (2) | 0.0003 (14) | 0.0147 (16) | 0.0052 (16) |
C17 | 0.082 (2) | 0.080 (2) | 0.066 (2) | −0.027 (2) | −0.0183 (19) | 0.0186 (18) |
C18 | 0.071 (2) | 0.080 (2) | 0.064 (2) | −0.0310 (19) | −0.0078 (18) | 0.0067 (18) |
C20 | 0.063 (2) | 0.069 (2) | 0.061 (2) | −0.0026 (17) | −0.0006 (17) | 0.0091 (16) |
C22 | 0.054 (2) | 0.098 (3) | 0.105 (3) | −0.015 (2) | −0.005 (2) | −0.022 (2) |
S1—C1 | 1.705 (3) | C1—H1 | 0.9300 |
S1—C4 | 1.725 (3) | C13—C12 | 1.376 (4) |
N1—C8 | 1.306 (3) | C13—H13 | 0.9300 |
N1—C6 | 1.389 (3) | C12—C11 | 1.379 (4) |
C9—C10 | 1.390 (3) | C12—H12 | 0.9300 |
C9—C14 | 1.395 (3) | C2—C3 | 1.398 (4) |
C9—C8 | 1.475 (3) | C2—H2 | 0.9300 |
N2—N3 | 1.398 (3) | C16—C17 | 1.369 (4) |
N2—C8 | 1.399 (3) | C16—C21 | 1.384 (4) |
N2—C7 | 1.410 (3) | C16—C15 | 1.456 (4) |
O1—C7 | 1.215 (3) | C15—H15 | 0.9300 |
C7—C6 | 1.475 (3) | C19—C18 | 1.353 (4) |
N3—C15 | 1.257 (3) | C19—C20 | 1.374 (4) |
C10—C11 | 1.380 (4) | C21—C20 | 1.371 (4) |
C10—H10 | 0.9300 | C21—H21 | 0.9300 |
C5—C6 | 1.349 (3) | C3—H3 | 0.9300 |
C5—C4 | 1.431 (3) | C11—H11 | 0.9300 |
C5—H5 | 0.9300 | C17—C18 | 1.388 (4) |
C14—C13 | 1.384 (4) | C17—H17 | 0.9300 |
C14—H14 | 0.9300 | C18—H18 | 0.9300 |
O2—C19 | 1.367 (3) | C20—H20 | 0.9300 |
O2—C22 | 1.426 (3) | C22—H22A | 0.9600 |
C4—C3 | 1.380 (3) | C22—H22B | 0.9600 |
C1—C2 | 1.345 (4) | C22—H22C | 0.9600 |
C1—S1—C4 | 91.37 (14) | C1—C2—H2 | 123.6 |
C8—N1—C6 | 106.9 (2) | C3—C2—H2 | 123.6 |
C10—C9—C14 | 118.4 (2) | C5—C6—N1 | 126.4 (2) |
C10—C9—C8 | 116.6 (2) | C5—C6—C7 | 123.5 (3) |
C14—C9—C8 | 125.0 (2) | N1—C6—C7 | 110.0 (2) |
N3—N2—C8 | 123.0 (2) | C17—C16—C21 | 117.0 (3) |
N3—N2—C7 | 128.3 (2) | C17—C16—C15 | 119.4 (3) |
C8—N2—C7 | 108.4 (2) | C21—C16—C15 | 123.6 (3) |
O1—C7—N2 | 127.0 (3) | N3—C15—C16 | 122.0 (3) |
O1—C7—C6 | 130.8 (3) | N3—C15—H15 | 119.0 |
N2—C7—C6 | 102.1 (2) | C16—C15—H15 | 119.0 |
N1—C8—N2 | 112.5 (2) | C18—C19—O2 | 124.4 (3) |
N1—C8—C9 | 121.6 (2) | C18—C19—C20 | 119.6 (3) |
N2—C8—C9 | 125.9 (2) | O2—C19—C20 | 115.9 (3) |
C15—N3—N2 | 118.3 (2) | C20—C21—C16 | 121.2 (3) |
C11—C10—C9 | 120.7 (3) | C20—C21—H21 | 119.4 |
C11—C10—H10 | 119.7 | C16—C21—H21 | 119.4 |
C9—C10—H10 | 119.7 | C4—C3—C2 | 112.7 (3) |
C6—C5—C4 | 128.3 (3) | C4—C3—H3 | 123.6 |
C6—C5—H5 | 115.8 | C2—C3—H3 | 123.6 |
C4—C5—H5 | 115.8 | C12—C11—C10 | 120.2 (3) |
C13—C14—C9 | 120.7 (3) | C12—C11—H11 | 119.9 |
C13—C14—H14 | 119.6 | C10—C11—H11 | 119.9 |
C9—C14—H14 | 119.6 | C16—C17—C18 | 122.2 (3) |
C19—O2—C22 | 117.6 (2) | C16—C17—H17 | 118.9 |
C3—C4—C5 | 124.6 (3) | C18—C17—H17 | 118.9 |
C3—C4—S1 | 110.5 (2) | C19—C18—C17 | 119.6 (3) |
C5—C4—S1 | 124.9 (2) | C19—C18—H18 | 120.2 |
C2—C1—S1 | 112.6 (2) | C17—C18—H18 | 120.2 |
C2—C1—H1 | 123.7 | C21—C20—C19 | 120.4 (3) |
S1—C1—H1 | 123.7 | C21—C20—H20 | 119.8 |
C12—C13—C14 | 119.9 (3) | C19—C20—H20 | 119.8 |
C12—C13—H13 | 120.0 | O2—C22—H22A | 109.5 |
C14—C13—H13 | 120.0 | O2—C22—H22B | 109.5 |
C13—C12—C11 | 120.0 (3) | H22A—C22—H22B | 109.5 |
C13—C12—H12 | 120.0 | O2—C22—H22C | 109.5 |
C11—C12—H12 | 120.0 | H22A—C22—H22C | 109.5 |
C1—C2—C3 | 112.9 (3) | H22B—C22—H22C | 109.5 |
N3—N2—C7—O1 | 7.1 (4) | C4—C5—C6—N1 | 4.4 (5) |
C8—N2—C7—O1 | −180.0 (3) | C4—C5—C6—C7 | −172.6 (2) |
N3—N2—C7—C6 | −170.7 (2) | C8—N1—C6—C5 | −174.8 (3) |
C8—N2—C7—C6 | 2.3 (3) | C8—N1—C6—C7 | 2.5 (3) |
C6—N1—C8—N2 | −1.0 (3) | O1—C7—C6—C5 | −3.1 (5) |
C6—N1—C8—C9 | −179.0 (2) | N2—C7—C6—C5 | 174.5 (2) |
N3—N2—C8—N1 | 172.4 (2) | O1—C7—C6—N1 | 179.5 (3) |
C7—N2—C8—N1 | −1.0 (3) | N2—C7—C6—N1 | −2.9 (3) |
N3—N2—C8—C9 | −9.6 (4) | N2—N3—C15—C16 | 179.1 (2) |
C7—N2—C8—C9 | 177.0 (2) | C17—C16—C15—N3 | −172.5 (3) |
C10—C9—C8—N1 | −10.9 (4) | C21—C16—C15—N3 | 8.1 (5) |
C14—C9—C8—N1 | 166.7 (2) | C22—O2—C19—C18 | −0.8 (4) |
C10—C9—C8—N2 | 171.4 (2) | C22—O2—C19—C20 | 178.1 (3) |
C14—C9—C8—N2 | −11.1 (4) | C17—C16—C21—C20 | 1.6 (5) |
C8—N2—N3—C15 | 166.7 (2) | C15—C16—C21—C20 | −179.0 (3) |
C7—N2—N3—C15 | −21.3 (4) | C5—C4—C3—C2 | −178.0 (2) |
C14—C9—C10—C11 | 0.6 (4) | S1—C4—C3—C2 | −0.3 (3) |
C8—C9—C10—C11 | 178.3 (2) | C1—C2—C3—C4 | −0.1 (4) |
C10—C9—C14—C13 | −0.7 (4) | C13—C12—C11—C10 | −0.5 (4) |
C8—C9—C14—C13 | −178.2 (2) | C9—C10—C11—C12 | 0.0 (4) |
C6—C5—C4—C3 | 176.1 (3) | C21—C16—C17—C18 | −2.4 (5) |
C6—C5—C4—S1 | −1.3 (4) | C15—C16—C17—C18 | 178.1 (3) |
C1—S1—C4—C3 | 0.5 (2) | O2—C19—C18—C17 | 179.3 (3) |
C1—S1—C4—C5 | 178.2 (2) | C20—C19—C18—C17 | 0.4 (5) |
C4—S1—C1—C2 | −0.6 (2) | C16—C17—C18—C19 | 1.5 (6) |
C9—C14—C13—C12 | 0.2 (4) | C16—C21—C20—C19 | 0.2 (5) |
C14—C13—C12—C11 | 0.4 (4) | C18—C19—C20—C21 | −1.2 (5) |
S1—C1—C2—C3 | 0.5 (3) | O2—C19—C20—C21 | 179.8 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10···N1 | 0.93 | 2.46 | 2.792 (4) | 101 |
C14—H14···N3 | 0.93 | 2.32 | 2.942 (4) | 124 |
C15—H15···O1 | 0.93 | 2.21 | 2.867 (3) | 127 |
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10···N1 | 0.93 | 2.46 | 2.792 (4) | 101 |
C14—H14···N3 | 0.93 | 2.32 | 2.942 (4) | 124 |
C15—H15···O1 | 0.93 | 2.21 | 2.867 (3) | 127 |
Experimental details
Crystal data | |
Chemical formula | C22H17N3O2S |
Mr | 387.45 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 20.6796 (18), 5.4004 (4), 17.2537 (16) |
β (°) | 104.299 (9) |
V (Å3) | 1867.2 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.20 |
Crystal size (mm) | 0.30 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur Sapphire3 |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2010) |
Tmin, Tmax | 0.769, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7300, 3663, 2215 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.136, 1.05 |
No. of reflections | 3663 |
No. of parameters | 255 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.24, −0.23 |
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. SNK acknowledges the Department of Chemistry, Shri MadhwaVadiraja Institute of Technology, Bantakal (VTU Belgam), for providing research facilities.
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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.
Compounds containing the imidazolone as well as the imine moiety exhibit an important role in pharmaceutical activities, such as antimicrobial (Suthakaran et al., 2008; Patel et al., 2006), antioxidant (Suhasini et al., 2014), anticonvulsant (Mohamed et al., 2012), anthelmintic (Patel et al., 2010) antibacterial (Solankee et al., 2011) analgesic (Sridhar & Ramesh, 2001), anti-inflammatory (Viveka et al., 2015), and antitumor (Hodnett & Dunn, 1970). Apart from biological activity, Schiff bases have assumed importance as ligands in coordination chemistry (Özkar et al. 2004, Pouralimardan et al., 2007; Patti et al., 2009). Structural information of the title compound is useful in developing coordination properties of Schiff bases and to investigate new ligands.
The molecular structure of the title compound is shown in Fig. 1. The bond lengths (Allen et al. 1987) and bond angles in the title compound have normal values and all aromatic rings are essentially planar. The imidazole ring forms dihedral angles of 9.2 (2)°, 10.9 (2)° and 12.5 (2)° with the thiophene [S1/C1-C4] , phenyl [C9-C14] and methoxy-substituted benzene [C16-C21] rings, respectively. The methoxy group is essentially planar with the benzene ring to which it is attached with a C22-O2-C19-C18 torsion angle of -0.8 (4)°. There are two intramolecular C—H···N hydrogen bonds forming S(5) and S(6) rings and one intramolecular C—H···O hydrogen bond forming an S(6) ring (Fig. 1).