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Acta Cryst. (2007). E63, o2840    [ doi:10.1107/S1600536807021587 ]

(5S)-1,4-Bis{[(1E)-4-methylbenzylidene]amino}-5-(thien-2-yl)pyrrolidin-2-one

D. Chopra, K. N. Venugopala and G. K. Rao

Abstract top

In the crystal structure of the title compound, C25H24SN4O2, the pyrrole ring adopts an envelope conformation. Each of the 4-methylbenzylidene units is planar and they make angles of 12.26 (8) and 85.46 (10)° with the four coplanar atoms of the pyrrole ring. The thiophene ring makes an angle of 75.06 (9)° with this plane. The crystal structure is stabilized by intermolecular N-H...O and C-H...O hydrogen bonds.

Comment top

2-Pyrrolidinone and its derivatives find widespread applications in drugs. These exhibit antidepressant or analeptic activity which affects the central nervous system. The alkyl-, aryl- and N-methylamine derivatives of 2-pyrrolidinone have been found to possess analgesic and anti-inflammatory activities (Malawska et al., 1982). Further, a series of N-(β-hydroxy-γ-aminopropyl)-2-pyrrolidinones provided treatment for cardiovascular problems (Malawska et al., 1988). One such important compound is the anti-arrhythmic and hypotensive agent 1-[2-Hydroxy-3-(4-phenyl-l- piperazinyl)propyl]pyrrolidin-2-one (Stadnicka et al., 1991).

In this paper we report the crystal structure of the pyrrolidinone derivative, (I). The five membered pyrrole ring exists in an envelope conformation with the atom C11 deviating by -0.379 (2)Å from the mean plane passing through the atoms C9—C10—C12—N4. The dihedral angle between the planes N1—C7—C1/C6—C26 and C13—O1—N3—N2—C15—C21—C27 with the thiophene ring are 87.2 (1)° and 58.3 (1)° respectively. The C—N bond lengths are different, indicating that the nitrogen atoms exist in a different electronic environment. The crystal structure is stabilized by N—H···O and C—H···O hydrogen bonds (involving H14 and H12 connected to chiral carbon C12) along the crystallographic screw 'b' axis, further stablilized by a C—H···O interaction (involving H1, Figure 2).

Related literature top

For the pharmaceutical applications of pyrrolidinone derivatives, see: Malawska et al. (1982, 1988); Stadnicka et al. (1991).

Experimental top

Methyl 4-acetoxybenzothiophen-6-carboxylate (25 g, 0.1 mol) and hydrazine hydrate 14.2 ml were heated gently under reflux for 10 min. Sufficient quantity of absolute alcohol was added to get a clear solution (about 10 ml). The resulting solution was refluxed for 3 h, ethanol distilled off and the product cooled. Crystals of acid hydrazide were filtered and recrystalized from ethanol. The product was isolated as white fluffy mass with yield of 16.26 g (78.20%). A mixture of 4-hydroxy benzothiophen-6-carboxhydrazide 0.208 g (0.001 mol) and p-methyl benzaldehyde 0.24 g (0.002 mol) in 50 ml of alcohol was refluxed for 2 hrs to yield the title compound which is recrystallized from ethanol to obtain crystals of 2-(2-thienyl)-1-(p-tolualdimino)-3-[N-(p-tolualdimino] carboxamido-1(H)-pyrrolidine-5-one 0.372 g (83.78%).

Refinement top

All H-atoms were positioned geometrically and refined using a riding model with d(C—H) = 0.93 Å, Uiso=1.2Ueq (C) for aromatic 0.98 Å, Uiso = 1.2Ueq (C) for CH, 0.97 Å, Uiso = 1.2Ueq (C) for CH2, 0.96 Å, Uiso = 1.2Ueq (C) for CH3 atoms and 0.82 Å, Uiso = 1.2Ueq (N) for the NH groups.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1999) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. A packing diagram of (I). The dotted lines depict N—H···O and C—H···O hydrogen bonds.
(5S)-1,4-Bis{[(1E)-4-methylbenzylidene]amino}-5-(thien-2-yl)pyrrolidin-2-one top
Crystal data top
C25H24N4O2SF(000) = 936
Mr = 444.55Dx = 1.240 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 750 reflections
a = 13.777 (3) Åθ = 1.4–25.8°
b = 7.6072 (14) ŵ = 0.16 mm−1
c = 23.431 (4) ÅT = 290 K
β = 104.167 (3)°Blocks, pale yellow
V = 2381.0 (8) Å30.30 × 0.20 × 0.20 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer		4510 independent reflections
Radiation source: fine-focus sealed tube2601 reflections with I > 2σ(I)
graphiteRint = 0.057
φ and ω scansθmax = 25.7°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1997)		h = −16→16
Tmin = 0.920, Tmax = 0.968k = −8→9
16794 measured reflectionsl = −28→28
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0582P)2]
where P = (Fo2 + 2Fc2)/3
4510 reflections(Δ/σ)max < 0.001
291 parametersΔρmax = 0.21 e Å−3
0 restraintsΔρmin = −0.19 e Å−3
Crystal data top
C25H24N4O2SV = 2381.0 (8) Å3
Mr = 444.55Z = 4
Monoclinic, P21/nMo Kα radiation
a = 13.777 (3) ŵ = 0.16 mm−1
b = 7.6072 (14) ÅT = 290 K
c = 23.431 (4) Å0.30 × 0.20 × 0.20 mm
β = 104.167 (3)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		4510 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1997)		2601 reflections with I > 2σ(I)
Tmin = 0.920, Tmax = 0.968Rint = 0.057
16794 measured reflectionsθmax = 25.7°
Refinement top
R[F2 > 2σ(F2)] = 0.062H-atom parameters constrained
wR(F2) = 0.140Δρmax = 0.21 e Å−3
S = 1.04Δρmin = −0.19 e Å−3
4510 reflectionsAbsolute structure: ?
291 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
xyzUiso*/Ueq
S1−0.06393 (6)0.02880 (10)0.06412 (3)0.0722 (3)
O10.21489 (16)−0.1631 (3)0.27430 (8)0.0780 (7)
O20.21631 (14)−0.3454 (2)0.10967 (7)0.0625 (5)
N10.24290 (15)−0.0011 (3)0.08651 (9)0.0477 (5)
N20.05556 (16)0.1972 (3)0.25946 (9)0.0505 (6)
N30.12607 (16)0.0747 (3)0.28518 (8)0.0550 (6)
N40.18454 (15)−0.0548 (3)0.12347 (8)0.0443 (5)
C10.3088 (2)0.3944 (4)0.02116 (13)0.0703 (9)
C20.3545 (3)0.4513 (5)−0.02215 (14)0.0854 (10)
C30.4016 (3)0.3363 (6)−0.05141 (14)0.0830 (11)
C40.4021 (2)0.1619 (6)−0.03596 (15)0.0889 (11)
C50.3563 (2)0.1024 (4)0.00675 (13)0.0749 (9)
C60.30875 (19)0.2201 (4)0.03586 (11)0.0520 (7)
C70.25474 (19)0.1619 (4)0.07904 (10)0.0504 (7)
C90.1716 (2)−0.2311 (4)0.12955 (10)0.0481 (7)
C100.0960 (2)−0.2550 (3)0.16454 (11)0.0562 (7)
C110.08397 (19)−0.0758 (3)0.19067 (10)0.0450 (6)
C120.12002 (17)0.0571 (3)0.14987 (9)0.0413 (6)
C130.1477 (2)−0.0613 (4)0.25350 (11)0.0504 (7)
C150.0506 (2)0.3362 (4)0.28833 (11)0.0539 (7)
C16−0.0205 (2)0.4754 (4)0.26443 (11)0.0524 (7)
C17−0.0213 (2)0.6294 (4)0.29555 (13)0.0682 (9)
C18−0.0852 (3)0.7654 (4)0.27262 (15)0.0757 (9)
C19−0.1503 (2)0.7547 (4)0.21827 (15)0.0684 (9)
C20−0.1500 (2)0.6005 (4)0.18697 (13)0.0721 (9)
C21−0.0874 (2)0.4634 (4)0.20952 (12)0.0625 (8)
C220.0261 (2)0.3155 (4)0.09161 (13)0.0642 (8)
C230.03622 (18)0.1436 (3)0.10518 (10)0.0426 (6)
C24−0.0625 (2)0.3547 (5)0.04874 (14)0.0801 (10)
C25−0.1175 (2)0.2139 (4)0.03023 (12)0.0714 (9)
C260.4504 (3)0.3978 (6)−0.09953 (15)0.1286 (16)
C27−0.2178 (3)0.9080 (5)0.19279 (17)0.1027 (12)
H10.27770.47570.04050.084*
H20.35320.5702−0.03150.102*
H40.43420.0813−0.05490.107*
H50.3575−0.01660.01590.090*
H70.22920.24400.10090.060*
H10A0.1188−0.34100.19550.067*
H10B0.0328−0.29460.13960.067*
H110.0134−0.05460.18970.054*
H120.16100.14800.17400.050*
H140.15660.08480.32170.066*
H150.09320.34970.32550.065*
H170.02190.64160.33260.082*
H18−0.08400.86730.29470.091*
H20−0.19310.58950.14980.086*
H21−0.08980.36070.18770.075*
H220.07290.40010.10880.077*
H24−0.08040.46770.03490.096*
H25−0.17820.21620.00210.086*
H26A0.40800.3687−0.13730.193*
H26B0.51400.3408−0.09490.193*
H26C0.45990.5228−0.09680.193*
H27A−0.28430.88600.19700.154*
H27B−0.21930.92090.15180.154*
H27C−0.19241.01380.21340.154*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0638 (5)0.0668 (6)0.0699 (5)−0.0075 (4)−0.0142 (4)−0.0071 (4)
O10.0810 (16)0.0805 (15)0.0621 (13)0.0295 (13)−0.0027 (11)0.0078 (11)
O20.0796 (14)0.0566 (13)0.0468 (10)0.0190 (11)0.0067 (10)−0.0048 (9)
N10.0425 (13)0.0582 (16)0.0412 (12)−0.0001 (11)0.0083 (10)−0.0031 (11)
N20.0503 (14)0.0602 (15)0.0409 (12)0.0024 (12)0.0110 (10)−0.0040 (12)
N30.0608 (15)0.0680 (16)0.0330 (11)0.0039 (13)0.0052 (10)−0.0007 (11)
N40.0441 (13)0.0470 (14)0.0417 (11)0.0007 (11)0.0105 (10)−0.0031 (10)
C10.081 (2)0.073 (2)0.0643 (19)−0.0034 (18)0.0315 (17)−0.0007 (17)
C20.105 (3)0.086 (3)0.071 (2)−0.011 (2)0.033 (2)0.010 (2)
C30.075 (2)0.121 (3)0.057 (2)−0.008 (2)0.0234 (17)0.009 (2)
C40.082 (3)0.121 (3)0.075 (2)0.015 (2)0.043 (2)−0.005 (2)
C50.074 (2)0.083 (2)0.078 (2)0.0114 (19)0.0374 (19)0.0056 (19)
C60.0448 (16)0.066 (2)0.0453 (15)−0.0007 (15)0.0122 (13)0.0013 (14)
C70.0453 (16)0.062 (2)0.0450 (15)−0.0027 (15)0.0125 (12)−0.0058 (14)
C90.0558 (18)0.0473 (19)0.0354 (14)0.0046 (15)−0.0002 (13)−0.0029 (13)
C100.0670 (19)0.0480 (17)0.0512 (16)−0.0044 (15)0.0100 (14)0.0001 (13)
C110.0456 (15)0.0468 (16)0.0426 (13)−0.0010 (13)0.0110 (12)0.0008 (12)
C120.0416 (15)0.0432 (15)0.0374 (13)−0.0048 (12)0.0061 (11)−0.0075 (11)
C130.0520 (17)0.0547 (18)0.0440 (15)0.0000 (15)0.0110 (13)0.0049 (14)
C150.0521 (17)0.066 (2)0.0443 (15)−0.0070 (16)0.0134 (13)−0.0059 (15)
C160.0504 (17)0.0595 (19)0.0532 (16)−0.0063 (15)0.0241 (14)−0.0115 (14)
C170.071 (2)0.077 (2)0.0572 (17)−0.0065 (19)0.0165 (16)−0.0166 (17)
C180.087 (3)0.064 (2)0.082 (2)0.001 (2)0.033 (2)−0.0223 (19)
C190.059 (2)0.071 (2)0.084 (2)0.0060 (17)0.0345 (18)−0.0041 (19)
C200.056 (2)0.091 (3)0.0673 (19)0.0133 (19)0.0117 (15)−0.0103 (19)
C210.0567 (18)0.070 (2)0.0602 (18)0.0030 (17)0.0129 (15)−0.0179 (16)
C220.064 (2)0.0454 (19)0.076 (2)0.0028 (15)0.0023 (16)−0.0037 (15)
C230.0454 (15)0.0446 (17)0.0369 (13)−0.0020 (13)0.0084 (11)−0.0084 (12)
C240.080 (2)0.067 (2)0.083 (2)0.021 (2)−0.0014 (19)0.0165 (19)
C250.063 (2)0.090 (2)0.0512 (17)0.0151 (19)−0.0056 (15)0.0024 (17)
C260.130 (4)0.200 (5)0.072 (2)−0.033 (3)0.055 (2)0.013 (3)
C270.089 (3)0.096 (3)0.130 (3)0.032 (2)0.040 (2)0.003 (2)
Geometric parameters (Å, °) top
S1—C251.695 (3)C21—C201.374 (4)
S1—C231.715 (2)C21—H210.9300
O2—C91.222 (3)C18—C191.369 (4)
N2—C151.266 (3)C18—C171.379 (4)
N2—N31.374 (3)C18—H180.9300
N4—C91.365 (3)C1—C21.389 (4)
N4—N11.380 (3)C1—H10.9300
N4—C121.472 (3)C20—C191.384 (4)
N1—C71.268 (3)C20—H200.9300
O1—C131.213 (3)C25—C241.322 (4)
N3—C131.349 (3)C25—H250.9300
N3—H140.8600C19—C271.519 (4)
C15—C161.459 (4)C5—C41.383 (4)
C15—H150.9300C5—H50.9300
C12—C231.507 (3)C17—H170.9300
C12—C111.554 (3)C22—C241.410 (4)
C12—H120.9800C22—H220.9300
C11—C101.520 (3)C24—H240.9300
C11—C131.522 (3)C2—C31.369 (4)
C11—H110.9800C2—H20.9300
C23—C221.345 (3)C4—C31.375 (4)
C6—C11.370 (4)C4—H40.9300
C6—C51.384 (4)C27—H27A0.9600
C6—C71.464 (3)C27—H27B0.9600
C9—C101.486 (4)C27—H27C0.9600
C16—C171.381 (4)C3—C261.521 (4)
C16—C211.390 (4)C26—H26A0.9600
C7—H70.9300C26—H26B0.9600
C10—H10A0.9700C26—H26C0.9600
C10—H10B0.9700
C25—S1—C2392.19 (15)C16—C21—H21119.4
C15—N2—N3117.2 (2)C19—C18—C17121.9 (3)
C9—N4—N1117.9 (2)C19—C18—H18119.1
C9—N4—C12114.6 (2)C17—C18—H18119.1
N1—N4—C12126.6 (2)C6—C1—C2120.9 (3)
C7—N1—N4119.4 (2)C6—C1—H1119.6
C13—N3—N2120.4 (2)C2—C1—H1119.6
C13—N3—H14119.8C21—C20—C19121.5 (3)
N2—N3—H14119.8C21—C20—H20119.2
N2—C15—C16121.3 (2)C19—C20—H20119.2
N2—C15—H15119.3C24—C25—S1111.7 (2)
C16—C15—H15119.3C24—C25—H25124.1
N4—C12—C23113.53 (18)S1—C25—H25124.1
N4—C12—C11101.47 (18)C18—C19—C20117.2 (3)
C23—C12—C11113.93 (19)C18—C19—C27121.2 (3)
N4—C12—H12109.2C20—C19—C27121.6 (3)
C23—C12—H12109.2C4—C5—C6120.0 (3)
C11—C12—H12109.2C4—C5—H5120.0
C10—C11—C13111.1 (2)C6—C5—H5120.0
C10—C11—C12104.66 (19)C18—C17—C16121.2 (3)
C13—C11—C12110.61 (19)C18—C17—H17119.4
C10—C11—H11110.1C16—C17—H17119.4
C13—C11—H11110.1C23—C22—C24113.3 (3)
C12—C11—H11110.1C23—C22—H22123.3
C22—C23—C12127.3 (2)C24—C22—H22123.3
C22—C23—S1109.85 (19)C25—C24—C22112.9 (3)
C12—C23—S1122.81 (19)C25—C24—H24123.6
C1—C6—C5118.2 (3)C22—C24—H24123.6
C1—C6—C7119.9 (3)C3—C2—C1121.5 (3)
C5—C6—C7121.8 (3)C3—C2—H2119.2
O1—C13—N3121.2 (2)C1—C2—H2119.2
O1—C13—C11123.0 (3)C3—C4—C5122.2 (3)
N3—C13—C11115.8 (2)C3—C4—H4118.9
O2—C9—N4124.6 (3)C5—C4—H4118.9
O2—C9—C10127.6 (3)C19—C27—H27A109.5
N4—C9—C10107.8 (2)C19—C27—H27B109.5
C17—C16—C21117.1 (3)H27A—C27—H27B109.5
C17—C16—C15120.3 (3)C19—C27—H27C109.5
C21—C16—C15122.6 (3)H27A—C27—H27C109.5
N1—C7—C6119.7 (3)H27B—C27—H27C109.5
N1—C7—H7120.1C2—C3—C4117.2 (3)
C6—C7—H7120.1C2—C3—C26121.6 (4)
C9—C10—C11105.8 (2)C4—C3—C26121.2 (4)
C9—C10—H10A110.6C3—C26—H26A109.5
C11—C10—H10A110.6C3—C26—H26B109.5
C9—C10—H10B110.6H26A—C26—H26B109.5
C11—C10—H10B110.6C3—C26—H26C109.5
H10A—C10—H10B108.7H26A—C26—H26C109.5
C20—C21—C16121.1 (3)H26B—C26—H26C109.5
C20—C21—H21119.4
C9—N4—N1—C7178.6 (2)C1—C6—C7—N1170.1 (3)
C12—N4—N1—C79.8 (3)C5—C6—C7—N1−6.5 (4)
C15—N2—N3—C13−168.5 (2)O2—C9—C10—C11166.2 (2)
N3—N2—C15—C16178.9 (2)N4—C9—C10—C11−13.1 (3)
C9—N4—C12—C23−106.6 (2)C13—C11—C10—C9−97.0 (2)
N1—N4—C12—C2362.6 (3)C12—C11—C10—C922.4 (3)
C9—N4—C12—C1116.1 (2)C17—C16—C21—C201.3 (4)
N1—N4—C12—C11−174.74 (19)C15—C16—C21—C20−176.7 (3)
N4—C12—C11—C10−22.7 (2)C5—C6—C1—C20.5 (4)
C23—C12—C11—C1099.7 (2)C7—C6—C1—C2−176.2 (3)
N4—C12—C11—C1397.1 (2)C16—C21—C20—C19−1.2 (5)
C23—C12—C11—C13−140.5 (2)C23—S1—C25—C240.3 (3)
N4—C12—C23—C22−110.8 (3)C17—C18—C19—C200.2 (5)
C11—C12—C23—C22133.7 (3)C17—C18—C19—C27−178.0 (3)
N4—C12—C23—S170.2 (3)C21—C20—C19—C180.4 (5)
C11—C12—C23—S1−45.3 (3)C21—C20—C19—C27178.6 (3)
C25—S1—C23—C22−0.5 (2)C1—C6—C5—C4−0.1 (4)
C25—S1—C23—C12178.6 (2)C7—C6—C5—C4176.6 (3)
N2—N3—C13—O1174.4 (2)C19—C18—C17—C16−0.1 (5)
N2—N3—C13—C11−4.7 (3)C21—C16—C17—C18−0.7 (4)
C10—C11—C13—O115.3 (4)C15—C16—C17—C18177.3 (3)
C12—C11—C13—O1−100.5 (3)C12—C23—C22—C24−178.5 (3)
C10—C11—C13—N3−165.6 (2)S1—C23—C22—C240.6 (3)
C12—C11—C13—N378.6 (3)S1—C25—C24—C220.0 (4)
N1—N4—C9—O28.2 (3)C23—C22—C24—C25−0.4 (4)
C12—N4—C9—O2178.4 (2)C6—C1—C2—C3−0.4 (5)
N1—N4—C9—C10−172.49 (19)C6—C5—C4—C3−0.6 (5)
C12—N4—C9—C10−2.3 (3)C1—C2—C3—C4−0.2 (5)
N2—C15—C16—C17−177.0 (3)C1—C2—C3—C26179.0 (3)
N2—C15—C16—C210.9 (4)C5—C4—C3—C20.7 (5)
N4—N1—C7—C6−174.4 (2)C5—C4—C3—C26−178.5 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C12—H12···O1i0.982.333.299 (3)168
N3—H14···O2i0.862.132.922 (2)152
C1—H1···O2ii0.932.423.337 (4)168
Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) x, y+1, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C12—H12···O1i0.982.333.299 (3)168
N3—H14···O2i0.862.132.922 (2)152
C1—H1···O2ii0.932.423.337 (4)168
Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) x, y+1, z.
Acknowledgements top

We thank Professor T. N. Guru Row and the Department of Science and Technology for data collection on the CCD facility under the IRHPA–DST scheme. DC thanks CSIR, India, and IISc for a Senior Research Fellowship.

references
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