Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807021587/sj2306sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807021587/sj2306Isup2.hkl |
CCDC reference: 651399
Key indicators
- Single-crystal X-ray study
- T = 290 K
- Mean (C-C) = 0.004 Å
- R factor = 0.062
- wR factor = 0.140
- Data-to-parameter ratio = 15.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.12 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.86 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C3 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C23
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C11 = ... R PLAT793_ALERT_1_G Check the Absolute Configuration of C12 = ... R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 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
For the pharmaceutical applications of pyrrolidinone derivatives, see: Malawska et al. (1982, 1988); Stadnicka et al. (1991).
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%).
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.
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).
For the pharmaceutical applications of pyrrolidinone derivatives, see: Malawska et al. (1982, 1988); Stadnicka et al. (1991).
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).
Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids. | |
Fig. 2. A packing diagram of (I). The dotted lines depict N—H···O and C—H···O hydrogen bonds. |
C25H24N4O2S | F(000) = 936 |
Mr = 444.55 | Dx = 1.240 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 750 reflections |
a = 13.777 (3) Å | θ = 1.4–25.8° |
b = 7.6072 (14) Å | µ = 0.16 mm−1 |
c = 23.431 (4) Å | T = 290 K |
β = 104.167 (3)° | Blocks, pale yellow |
V = 2381.0 (8) Å3 | 0.30 × 0.20 × 0.20 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 4510 independent reflections |
Radiation source: fine-focus sealed tube | 2601 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.057 |
φ and ω scans | θmax = 25.7°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | h = −16→16 |
Tmin = 0.920, Tmax = 0.968 | k = −8→9 |
16794 measured reflections | l = −28→28 |
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)] = 0.062 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.140 | H-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 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
C25H24N4O2S | V = 2381.0 (8) Å3 |
Mr = 444.55 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 13.777 (3) Å | µ = 0.16 mm−1 |
b = 7.6072 (14) Å | T = 290 K |
c = 23.431 (4) Å | 0.30 × 0.20 × 0.20 mm |
β = 104.167 (3)° |
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 = 0.968 | Rint = 0.057 |
16794 measured reflections |
R[F2 > 2σ(F2)] = 0.062 | 0 restraints |
wR(F2) = 0.140 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.21 e Å−3 |
4510 reflections | Δρmin = −0.19 e Å−3 |
291 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 | ||
S1 | −0.06393 (6) | 0.02880 (10) | 0.06412 (3) | 0.0722 (3) | |
O1 | 0.21489 (16) | −0.1631 (3) | 0.27430 (8) | 0.0780 (7) | |
O2 | 0.21631 (14) | −0.3454 (2) | 0.10967 (7) | 0.0625 (5) | |
N1 | 0.24290 (15) | −0.0011 (3) | 0.08651 (9) | 0.0477 (5) | |
N2 | 0.05556 (16) | 0.1972 (3) | 0.25946 (9) | 0.0505 (6) | |
N3 | 0.12607 (16) | 0.0747 (3) | 0.28518 (8) | 0.0550 (6) | |
N4 | 0.18454 (15) | −0.0548 (3) | 0.12347 (8) | 0.0443 (5) | |
C1 | 0.3088 (2) | 0.3944 (4) | 0.02116 (13) | 0.0703 (9) | |
C2 | 0.3545 (3) | 0.4513 (5) | −0.02215 (14) | 0.0854 (10) | |
C3 | 0.4016 (3) | 0.3363 (6) | −0.05141 (14) | 0.0830 (11) | |
C4 | 0.4021 (2) | 0.1619 (6) | −0.03596 (15) | 0.0889 (11) | |
C5 | 0.3563 (2) | 0.1024 (4) | 0.00675 (13) | 0.0749 (9) | |
C6 | 0.30875 (19) | 0.2201 (4) | 0.03586 (11) | 0.0520 (7) | |
C7 | 0.25474 (19) | 0.1619 (4) | 0.07904 (10) | 0.0504 (7) | |
C9 | 0.1716 (2) | −0.2311 (4) | 0.12955 (10) | 0.0481 (7) | |
C10 | 0.0960 (2) | −0.2550 (3) | 0.16454 (11) | 0.0562 (7) | |
C11 | 0.08397 (19) | −0.0758 (3) | 0.19067 (10) | 0.0450 (6) | |
C12 | 0.12002 (17) | 0.0571 (3) | 0.14987 (9) | 0.0413 (6) | |
C13 | 0.1477 (2) | −0.0613 (4) | 0.25350 (11) | 0.0504 (7) | |
C15 | 0.0506 (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) | |
C22 | 0.0261 (2) | 0.3155 (4) | 0.09161 (13) | 0.0642 (8) | |
C23 | 0.03622 (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) | |
C26 | 0.4504 (3) | 0.3978 (6) | −0.09953 (15) | 0.1286 (16) | |
C27 | −0.2178 (3) | 0.9080 (5) | 0.19279 (17) | 0.1027 (12) | |
H1 | 0.2777 | 0.4757 | 0.0405 | 0.084* | |
H2 | 0.3532 | 0.5702 | −0.0315 | 0.102* | |
H4 | 0.4342 | 0.0813 | −0.0549 | 0.107* | |
H5 | 0.3575 | −0.0166 | 0.0159 | 0.090* | |
H7 | 0.2292 | 0.2440 | 0.1009 | 0.060* | |
H10A | 0.1188 | −0.3410 | 0.1955 | 0.067* | |
H10B | 0.0328 | −0.2946 | 0.1396 | 0.067* | |
H11 | 0.0134 | −0.0546 | 0.1897 | 0.054* | |
H12 | 0.1610 | 0.1480 | 0.1740 | 0.050* | |
H14 | 0.1566 | 0.0848 | 0.3217 | 0.066* | |
H15 | 0.0932 | 0.3497 | 0.3255 | 0.065* | |
H17 | 0.0219 | 0.6416 | 0.3326 | 0.082* | |
H18 | −0.0840 | 0.8673 | 0.2947 | 0.091* | |
H20 | −0.1931 | 0.5895 | 0.1498 | 0.086* | |
H21 | −0.0898 | 0.3607 | 0.1877 | 0.075* | |
H22 | 0.0729 | 0.4001 | 0.1088 | 0.077* | |
H24 | −0.0804 | 0.4677 | 0.0349 | 0.096* | |
H25 | −0.1782 | 0.2162 | 0.0021 | 0.086* | |
H26A | 0.4080 | 0.3687 | −0.1373 | 0.193* | |
H26B | 0.5140 | 0.3408 | −0.0949 | 0.193* | |
H26C | 0.4599 | 0.5228 | −0.0968 | 0.193* | |
H27A | −0.2843 | 0.8860 | 0.1970 | 0.154* | |
H27B | −0.2193 | 0.9209 | 0.1518 | 0.154* | |
H27C | −0.1924 | 1.0138 | 0.2134 | 0.154* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0638 (5) | 0.0668 (6) | 0.0699 (5) | −0.0075 (4) | −0.0142 (4) | −0.0071 (4) |
O1 | 0.0810 (16) | 0.0805 (15) | 0.0621 (13) | 0.0295 (13) | −0.0027 (11) | 0.0078 (11) |
O2 | 0.0796 (14) | 0.0566 (13) | 0.0468 (10) | 0.0190 (11) | 0.0067 (10) | −0.0048 (9) |
N1 | 0.0425 (13) | 0.0582 (16) | 0.0412 (12) | −0.0001 (11) | 0.0083 (10) | −0.0031 (11) |
N2 | 0.0503 (14) | 0.0602 (15) | 0.0409 (12) | 0.0024 (12) | 0.0110 (10) | −0.0040 (12) |
N3 | 0.0608 (15) | 0.0680 (16) | 0.0330 (11) | 0.0039 (13) | 0.0052 (10) | −0.0007 (11) |
N4 | 0.0441 (13) | 0.0470 (14) | 0.0417 (11) | 0.0007 (11) | 0.0105 (10) | −0.0031 (10) |
C1 | 0.081 (2) | 0.073 (2) | 0.0643 (19) | −0.0034 (18) | 0.0315 (17) | −0.0007 (17) |
C2 | 0.105 (3) | 0.086 (3) | 0.071 (2) | −0.011 (2) | 0.033 (2) | 0.010 (2) |
C3 | 0.075 (2) | 0.121 (3) | 0.057 (2) | −0.008 (2) | 0.0234 (17) | 0.009 (2) |
C4 | 0.082 (3) | 0.121 (3) | 0.075 (2) | 0.015 (2) | 0.043 (2) | −0.005 (2) |
C5 | 0.074 (2) | 0.083 (2) | 0.078 (2) | 0.0114 (19) | 0.0374 (19) | 0.0056 (19) |
C6 | 0.0448 (16) | 0.066 (2) | 0.0453 (15) | −0.0007 (15) | 0.0122 (13) | 0.0013 (14) |
C7 | 0.0453 (16) | 0.062 (2) | 0.0450 (15) | −0.0027 (15) | 0.0125 (12) | −0.0058 (14) |
C9 | 0.0558 (18) | 0.0473 (19) | 0.0354 (14) | 0.0046 (15) | −0.0002 (13) | −0.0029 (13) |
C10 | 0.0670 (19) | 0.0480 (17) | 0.0512 (16) | −0.0044 (15) | 0.0100 (14) | 0.0001 (13) |
C11 | 0.0456 (15) | 0.0468 (16) | 0.0426 (13) | −0.0010 (13) | 0.0110 (12) | 0.0008 (12) |
C12 | 0.0416 (15) | 0.0432 (15) | 0.0374 (13) | −0.0048 (12) | 0.0061 (11) | −0.0075 (11) |
C13 | 0.0520 (17) | 0.0547 (18) | 0.0440 (15) | 0.0000 (15) | 0.0110 (13) | 0.0049 (14) |
C15 | 0.0521 (17) | 0.066 (2) | 0.0443 (15) | −0.0070 (16) | 0.0134 (13) | −0.0059 (15) |
C16 | 0.0504 (17) | 0.0595 (19) | 0.0532 (16) | −0.0063 (15) | 0.0241 (14) | −0.0115 (14) |
C17 | 0.071 (2) | 0.077 (2) | 0.0572 (17) | −0.0065 (19) | 0.0165 (16) | −0.0166 (17) |
C18 | 0.087 (3) | 0.064 (2) | 0.082 (2) | 0.001 (2) | 0.033 (2) | −0.0223 (19) |
C19 | 0.059 (2) | 0.071 (2) | 0.084 (2) | 0.0060 (17) | 0.0345 (18) | −0.0041 (19) |
C20 | 0.056 (2) | 0.091 (3) | 0.0673 (19) | 0.0133 (19) | 0.0117 (15) | −0.0103 (19) |
C21 | 0.0567 (18) | 0.070 (2) | 0.0602 (18) | 0.0030 (17) | 0.0129 (15) | −0.0179 (16) |
C22 | 0.064 (2) | 0.0454 (19) | 0.076 (2) | 0.0028 (15) | 0.0023 (16) | −0.0037 (15) |
C23 | 0.0454 (15) | 0.0446 (17) | 0.0369 (13) | −0.0020 (13) | 0.0084 (11) | −0.0084 (12) |
C24 | 0.080 (2) | 0.067 (2) | 0.083 (2) | 0.021 (2) | −0.0014 (19) | 0.0165 (19) |
C25 | 0.063 (2) | 0.090 (2) | 0.0512 (17) | 0.0151 (19) | −0.0056 (15) | 0.0024 (17) |
C26 | 0.130 (4) | 0.200 (5) | 0.072 (2) | −0.033 (3) | 0.055 (2) | 0.013 (3) |
C27 | 0.089 (3) | 0.096 (3) | 0.130 (3) | 0.032 (2) | 0.040 (2) | 0.003 (2) |
S1—C25 | 1.695 (3) | C21—C20 | 1.374 (4) |
S1—C23 | 1.715 (2) | C21—H21 | 0.9300 |
O2—C9 | 1.222 (3) | C18—C19 | 1.369 (4) |
N2—C15 | 1.266 (3) | C18—C17 | 1.379 (4) |
N2—N3 | 1.374 (3) | C18—H18 | 0.9300 |
N4—C9 | 1.365 (3) | C1—C2 | 1.389 (4) |
N4—N1 | 1.380 (3) | C1—H1 | 0.9300 |
N4—C12 | 1.472 (3) | C20—C19 | 1.384 (4) |
N1—C7 | 1.268 (3) | C20—H20 | 0.9300 |
O1—C13 | 1.213 (3) | C25—C24 | 1.322 (4) |
N3—C13 | 1.349 (3) | C25—H25 | 0.9300 |
N3—H14 | 0.8600 | C19—C27 | 1.519 (4) |
C15—C16 | 1.459 (4) | C5—C4 | 1.383 (4) |
C15—H15 | 0.9300 | C5—H5 | 0.9300 |
C12—C23 | 1.507 (3) | C17—H17 | 0.9300 |
C12—C11 | 1.554 (3) | C22—C24 | 1.410 (4) |
C12—H12 | 0.9800 | C22—H22 | 0.9300 |
C11—C10 | 1.520 (3) | C24—H24 | 0.9300 |
C11—C13 | 1.522 (3) | C2—C3 | 1.369 (4) |
C11—H11 | 0.9800 | C2—H2 | 0.9300 |
C23—C22 | 1.345 (3) | C4—C3 | 1.375 (4) |
C6—C1 | 1.370 (4) | C4—H4 | 0.9300 |
C6—C5 | 1.384 (4) | C27—H27A | 0.9600 |
C6—C7 | 1.464 (3) | C27—H27B | 0.9600 |
C9—C10 | 1.486 (4) | C27—H27C | 0.9600 |
C16—C17 | 1.381 (4) | C3—C26 | 1.521 (4) |
C16—C21 | 1.390 (4) | C26—H26A | 0.9600 |
C7—H7 | 0.9300 | C26—H26B | 0.9600 |
C10—H10A | 0.9700 | C26—H26C | 0.9600 |
C10—H10B | 0.9700 | ||
C25—S1—C23 | 92.19 (15) | C16—C21—H21 | 119.4 |
C15—N2—N3 | 117.2 (2) | C19—C18—C17 | 121.9 (3) |
C9—N4—N1 | 117.9 (2) | C19—C18—H18 | 119.1 |
C9—N4—C12 | 114.6 (2) | C17—C18—H18 | 119.1 |
N1—N4—C12 | 126.6 (2) | C6—C1—C2 | 120.9 (3) |
C7—N1—N4 | 119.4 (2) | C6—C1—H1 | 119.6 |
C13—N3—N2 | 120.4 (2) | C2—C1—H1 | 119.6 |
C13—N3—H14 | 119.8 | C21—C20—C19 | 121.5 (3) |
N2—N3—H14 | 119.8 | C21—C20—H20 | 119.2 |
N2—C15—C16 | 121.3 (2) | C19—C20—H20 | 119.2 |
N2—C15—H15 | 119.3 | C24—C25—S1 | 111.7 (2) |
C16—C15—H15 | 119.3 | C24—C25—H25 | 124.1 |
N4—C12—C23 | 113.53 (18) | S1—C25—H25 | 124.1 |
N4—C12—C11 | 101.47 (18) | C18—C19—C20 | 117.2 (3) |
C23—C12—C11 | 113.93 (19) | C18—C19—C27 | 121.2 (3) |
N4—C12—H12 | 109.2 | C20—C19—C27 | 121.6 (3) |
C23—C12—H12 | 109.2 | C4—C5—C6 | 120.0 (3) |
C11—C12—H12 | 109.2 | C4—C5—H5 | 120.0 |
C10—C11—C13 | 111.1 (2) | C6—C5—H5 | 120.0 |
C10—C11—C12 | 104.66 (19) | C18—C17—C16 | 121.2 (3) |
C13—C11—C12 | 110.61 (19) | C18—C17—H17 | 119.4 |
C10—C11—H11 | 110.1 | C16—C17—H17 | 119.4 |
C13—C11—H11 | 110.1 | C23—C22—C24 | 113.3 (3) |
C12—C11—H11 | 110.1 | C23—C22—H22 | 123.3 |
C22—C23—C12 | 127.3 (2) | C24—C22—H22 | 123.3 |
C22—C23—S1 | 109.85 (19) | C25—C24—C22 | 112.9 (3) |
C12—C23—S1 | 122.81 (19) | C25—C24—H24 | 123.6 |
C1—C6—C5 | 118.2 (3) | C22—C24—H24 | 123.6 |
C1—C6—C7 | 119.9 (3) | C3—C2—C1 | 121.5 (3) |
C5—C6—C7 | 121.8 (3) | C3—C2—H2 | 119.2 |
O1—C13—N3 | 121.2 (2) | C1—C2—H2 | 119.2 |
O1—C13—C11 | 123.0 (3) | C3—C4—C5 | 122.2 (3) |
N3—C13—C11 | 115.8 (2) | C3—C4—H4 | 118.9 |
O2—C9—N4 | 124.6 (3) | C5—C4—H4 | 118.9 |
O2—C9—C10 | 127.6 (3) | C19—C27—H27A | 109.5 |
N4—C9—C10 | 107.8 (2) | C19—C27—H27B | 109.5 |
C17—C16—C21 | 117.1 (3) | H27A—C27—H27B | 109.5 |
C17—C16—C15 | 120.3 (3) | C19—C27—H27C | 109.5 |
C21—C16—C15 | 122.6 (3) | H27A—C27—H27C | 109.5 |
N1—C7—C6 | 119.7 (3) | H27B—C27—H27C | 109.5 |
N1—C7—H7 | 120.1 | C2—C3—C4 | 117.2 (3) |
C6—C7—H7 | 120.1 | C2—C3—C26 | 121.6 (4) |
C9—C10—C11 | 105.8 (2) | C4—C3—C26 | 121.2 (4) |
C9—C10—H10A | 110.6 | C3—C26—H26A | 109.5 |
C11—C10—H10A | 110.6 | C3—C26—H26B | 109.5 |
C9—C10—H10B | 110.6 | H26A—C26—H26B | 109.5 |
C11—C10—H10B | 110.6 | C3—C26—H26C | 109.5 |
H10A—C10—H10B | 108.7 | H26A—C26—H26C | 109.5 |
C20—C21—C16 | 121.1 (3) | H26B—C26—H26C | 109.5 |
C20—C21—H21 | 119.4 | ||
C9—N4—N1—C7 | 178.6 (2) | C1—C6—C7—N1 | 170.1 (3) |
C12—N4—N1—C7 | 9.8 (3) | C5—C6—C7—N1 | −6.5 (4) |
C15—N2—N3—C13 | −168.5 (2) | O2—C9—C10—C11 | 166.2 (2) |
N3—N2—C15—C16 | 178.9 (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—C23 | 62.6 (3) | C12—C11—C10—C9 | 22.4 (3) |
C9—N4—C12—C11 | 16.1 (2) | C17—C16—C21—C20 | 1.3 (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—C2 | 0.5 (4) |
C23—C12—C11—C10 | 99.7 (2) | C7—C6—C1—C2 | −176.2 (3) |
N4—C12—C11—C13 | 97.1 (2) | C16—C21—C20—C19 | −1.2 (5) |
C23—C12—C11—C13 | −140.5 (2) | C23—S1—C25—C24 | 0.3 (3) |
N4—C12—C23—C22 | −110.8 (3) | C17—C18—C19—C20 | 0.2 (5) |
C11—C12—C23—C22 | 133.7 (3) | C17—C18—C19—C27 | −178.0 (3) |
N4—C12—C23—S1 | 70.2 (3) | C21—C20—C19—C18 | 0.4 (5) |
C11—C12—C23—S1 | −45.3 (3) | C21—C20—C19—C27 | 178.6 (3) |
C25—S1—C23—C22 | −0.5 (2) | C1—C6—C5—C4 | −0.1 (4) |
C25—S1—C23—C12 | 178.6 (2) | C7—C6—C5—C4 | 176.6 (3) |
N2—N3—C13—O1 | 174.4 (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—O1 | 15.3 (4) | C15—C16—C17—C18 | 177.3 (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—C24 | 0.6 (3) |
C12—C11—C13—N3 | 78.6 (3) | S1—C25—C24—C22 | 0.0 (4) |
N1—N4—C9—O2 | 8.2 (3) | C23—C22—C24—C25 | −0.4 (4) |
C12—N4—C9—O2 | 178.4 (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—C26 | 179.0 (3) |
N2—C15—C16—C21 | 0.9 (4) | C5—C4—C3—C2 | 0.7 (5) |
N4—N1—C7—C6 | −174.4 (2) | C5—C4—C3—C26 | −178.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12···O1i | 0.98 | 2.33 | 3.299 (3) | 168 |
N3—H14···O2i | 0.86 | 2.13 | 2.922 (2) | 152 |
C1—H1···O2ii | 0.93 | 2.42 | 3.337 (4) | 168 |
Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C25H24N4O2S |
Mr | 444.55 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 290 |
a, b, c (Å) | 13.777 (3), 7.6072 (14), 23.431 (4) |
β (°) | 104.167 (3) |
V (Å3) | 2381.0 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.16 |
Crystal size (mm) | 0.30 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1997) |
Tmin, Tmax | 0.920, 0.968 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16794, 4510, 2601 |
Rint | 0.057 |
(sin θ/λ)max (Å−1) | 0.610 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.062, 0.140, 1.04 |
No. of reflections | 4510 |
No. of parameters | 291 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.21, −0.19 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SAINT, SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1999) and CAMERON (Watkin et al., 1993), PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12···O1i | 0.98 | 2.33 | 3.299 (3) | 168 |
N3—H14···O2i | 0.86 | 2.13 | 2.922 (2) | 152 |
C1—H1···O2ii | 0.93 | 2.42 | 3.337 (4) | 168 |
Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) x, y+1, z. |
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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).