N-[4-Acetyl-5-(3-methoxy­phen­yl)-4,5-dihydro-1,3,4-thia­diazol-2-yl]acetamide

Aridoss, G.; Amirthaganesan, S.; Velmurugan, D.; Kim, S.H.; Jeong, Y.T.

doi:10.1107/S1600536808032108

organic compounds

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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2096

doi:10.1107/S1600536808032108

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N-[4-Acetyl-5-(3-methoxyphenyl)-4,5-dihydro-1,3,4-thiadiazol-2-yl]acetamide

G. Aridoss,^a S. Amirthaganesan,^a D. Velmurugan,^b S. H. Kim ^a and Y. T. Jeong ^a ^*

^aDivision of Image and Information Engineering, Pukyong National University, Busan 608-739, Republic of Korea, and ^bCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: ytjeong@pknu.ac.kr

(Received 29 September 2008; accepted 6 October 2008; online 11 October 2008)

The title compound, C₁₃H₁₅N₃O₃S, crystallizes with two molecules in the asymmetric unit. The thiadiazole rings in both the molecules adopt an envelope conformation. The crystal packing is stabilized by intermolecular N—H⋯O and C—H⋯O interactions.

Related literature

For biological activities of thiadiazole derivatives, see: Balasubramanian et al. (2004 ); Li et al. (2001 ); Radwan et al. (2007 ); Supuran et al. (2001 ). For ring conformational analysis, see: Cremer & Pople (1975 ); Nardelli (1983 ).

Experimental

Crystal data

C₁₃H₁₅N₃O₃S
M_r = 293.34
Monoclinic, P 2₁
a = 11.3790 (4) Å
b = 10.5993 (3) Å
c = 11.9596 (2) Å
β = 108.225 (2)°
V = 1370.08 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 293 (2) K
0.30 × 0.20 × 0.16 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1999 ) T_min = 0.930, T_max = 0.962
16660 measured reflections
7595 independent reflections
5635 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.109
S = 1.03
7595 reflections
367 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.25 e Å⁻³
Absolute structure: Flack (1983 ), with 3584 Friedel pairs
Flack parameter: 0.07 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O5ⁱ	0.86	1.95	2.801 (3)	171
N6—H6A⋯O2ⁱⁱ	0.86	1.96	2.799 (3)	164
C25—H25C⋯O2ⁱⁱ	0.96	2.37	3.238 (4)	150
Symmetry codes: (i) $[-x+2, y+{\script{1\over 2}}, -z+1]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+1]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808032108/bt2802sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808032108/bt2802Isup2.hkl

checkCIF report

Comment top

Nitrogen heterocycles are one of the most important classes of biologically active compounds. Suitably substituted 1,3,4-thiadiazoles have attracted great attention owing to their broad spectrum of biological activities in the areas of medicine which includes antimicrobial, antituberculosis, anesthetic, antithrombotic, anticonvulsant, antihypertensive, anti-inflammatory and antiulcer activities (Balasubramanian et al., 2004; Li et al., 2001; Radwan et al. 2007; Supuran et al., 2001). Their action depends directly on the type and location of polar substituents on the heterocyclic ring. In general, pharmacological effect of potential drugs depends sensitively and solely on the stereochemistry and ring conformations. Thus, by keeping in view the promising biological potency of 1,3,4-thiadiazoles and variously substituted 1,3,4-thiadiazole frameworks, we have carried out the crystal structure determination of the title compound.

The title compound crystallizes with two molecules in the asymmetric unit. The sum of the angles at N1 (359.9 (6)°) and N4 (360.0 (6)°) are in accordance with sp² hybridization. The torsion angles around C6—C1—O1—C13 [0.0 (4)°] and C19—C14—O4—C26 [-1.8 (4)°] indicates the coplanarity of the methoxy groups with the corresponding phenyl rings (C1–C6) and (C14–C19), respectively. The thiadiazole ring in both the molecules adopt envelope conformation with atoms C7 and C20 deviating by 0.395 (3) and 0.350 (3) Å, respectively, from the mean plane of the remaining atoms. The puckering parameters (Cremer & Pople, 1975) and the smallest displacement asymmetry parameters (Nardelli, 1983) for the thiadiazole rings C10—S2—C7—N1—N2 and C20—S2—C23—N5—N4 are q₂ = 0.245 (2), 0.217 (2) Å, ϕ = 36.4 (6), 215.4 (6)° and Δ_s(C₇) = 6.9 (2), Δ_s(C₂₀) = 5.4 (2), respectively. N—H···O and C—H···O intermolecular interactions stabilize the crystal packing (Table 1).

Related literature top

For biological activities of thiadiazole derivatives, see: Balasubramanian et al. (2004); Li et al. (2001); Radwan et al. (2007); Supuran et al. (2001). For ring conformational analysis, see: Cremer & Pople (1975); Nardelli (1983).

Experimental top

The title compound was obtained by applying the method of Balasubramanian et al. (2004). 3-Methoxybenzadehyde thiosemicarbazone obtained by the reaction of 3-Methoxybenzadehyde and thiosemicarbazide was refluxed with excess of freshly distilled acetic anhydride on a water bath for about 7 h. After the completion of reaction, the excess of acetic anhydride was distilled off under reduced pressure and the obtained crude mass was purified by column chromatography (benzene–ethylacetate 5:1 v/v). Crystals were obtained from the solution of freshly distilled ethanol by slow evaporation at room temperature. ¹H NMR (DMSO-d₆, p.p.m.): 10.90 (s, 1H, amide NH); 7.36–6.76 (m, 5H, aromatic and ring methine protons); 3.78 (s, 3H, OCH₃); 2.38 (s, 3H, –COCH₃); 2.28 (s, 3H, –COCH₃).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004) and SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004) and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids.
	Fig. 2. The molecular packing of the title compound. For clarity, hydrogen atoms which are not involved in hydrogen bonding were omitted.

N-[4-Acetyl-5-(3-methoxyphenyl)-4,5-dihydro-1,3,4-thiadiazol-2-yl]acetamide top

Crystal data top

C₁₃H₁₅N₃O₃S	F(000) = 616
M_r = 293.34	D_x = 1.422 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 5353 reflections
a = 11.3790 (4) Å	θ = 1.8–29.6°
b = 10.5993 (3) Å	µ = 0.25 mm⁻¹
c = 11.9596 (2) Å	T = 293 K
β = 108.225 (2)°	Prism, colourless
V = 1370.08 (7) Å³	0.30 × 0.20 × 0.16 mm
Z = 4

Data collection top

Bruker Kappa-APEXII CCD diffractometer	7595 independent reflections
Radiation source: fine-focus sealed tube	5635 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ω and ϕ scans	θ_max = 29.6°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −15→15
T_min = 0.930, T_max = 0.962	k = −14→14
16660 measured reflections	l = −14→16

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.042	H-atom parameters constrained
wR(F²) = 0.109	w = 1/[σ²(F_o²) + (0.0466P)² + 0.2666P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
7595 reflections	Δρ_max = 0.33 e Å⁻³
367 parameters	Δρ_min = −0.25 e Å⁻³
1 restraint	Absolute structure: Flack (1983), with 3584 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.07 (7)

Crystal data top

C₁₃H₁₅N₃O₃S	V = 1370.08 (7) Å³
M_r = 293.34	Z = 4
Monoclinic, P2₁	Mo Kα radiation
a = 11.3790 (4) Å	µ = 0.25 mm⁻¹
b = 10.5993 (3) Å	T = 293 K
c = 11.9596 (2) Å	0.30 × 0.20 × 0.16 mm
β = 108.225 (2)°

Data collection top

Bruker Kappa-APEXII CCD diffractometer	7595 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1999)	5635 reflections with I > 2σ(I)
T_min = 0.930, T_max = 0.962	R_int = 0.030
16660 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	H-atom parameters constrained
wR(F²) = 0.109	Δρ_max = 0.33 e Å⁻³
S = 1.03	Δρ_min = −0.25 e Å⁻³
7595 reflections	Absolute structure: Flack (1983), with 3584 Friedel pairs
367 parameters	Absolute structure parameter: 0.07 (7)
1 restraint

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

	x	y	z	U_iso*/U_eq
C1	0.5869 (2)	0.7772 (2)	0.4618 (2)	0.0397 (5)
C2	0.6405 (3)	0.8511 (3)	0.3955 (3)	0.0498 (8)
H2	0.6027	0.8595	0.3148	0.060*
C3	0.7499 (3)	0.9119 (3)	0.4499 (2)	0.0538 (7)
H3	0.7862	0.9615	0.4055	0.065*
C4	0.8069 (2)	0.9005 (3)	0.5697 (2)	0.0442 (6)
H4	0.8808	0.9428	0.6055	0.053*
C5	0.7547 (2)	0.8268 (2)	0.6360 (2)	0.0309 (5)
C6	0.64253 (18)	0.7665 (2)	0.5812 (2)	0.0350 (5)
H6	0.6051	0.7186	0.6258	0.042*
C7	0.8123 (2)	0.8112 (3)	0.7677 (2)	0.0324 (6)
H7	0.7546	0.8419	0.8076	0.039*
C8	0.9343 (2)	1.0017 (3)	0.8382 (2)	0.0363 (6)
C9	1.0571 (2)	1.0645 (3)	0.8708 (3)	0.0441 (7)
H9A	1.0464	1.1541	0.8742	0.066*
H9B	1.0969	1.0455	0.8129	0.066*
H9C	1.1074	1.0346	0.9464	0.066*
C10	1.0096 (2)	0.6892 (3)	0.8300 (2)	0.0315 (6)
C11	1.0879 (3)	0.4753 (3)	0.8707 (2)	0.0390 (6)
C12	1.1970 (3)	0.3942 (3)	0.8773 (3)	0.0569 (8)
H12A	1.1920	0.3658	0.7997	0.085*
H12B	1.1975	0.3226	0.9267	0.085*
H12C	1.2716	0.4420	0.9098	0.085*
C13	0.4198 (2)	0.6425 (3)	0.4616 (3)	0.0548 (7)
H13A	0.3971	0.6925	0.5186	0.082*
H13B	0.4748	0.5763	0.5011	0.082*
H13C	0.3468	0.6062	0.4074	0.082*
C14	0.8900 (2)	0.2827 (3)	0.5333 (2)	0.0431 (6)
C15	0.8399 (3)	0.3437 (3)	0.6089 (3)	0.0499 (8)
H15	0.8734	0.3319	0.6897	0.060*
C16	0.7400 (3)	0.4223 (3)	0.5648 (2)	0.0524 (7)
H16	0.7053	0.4623	0.6162	0.063*
C17	0.6906 (2)	0.4425 (2)	0.4454 (2)	0.0420 (6)
H17	0.6236	0.4967	0.4164	0.050*
C18	0.7410 (2)	0.3820 (3)	0.3691 (2)	0.0313 (5)
C19	0.84171 (19)	0.3018 (2)	0.4136 (2)	0.0365 (5)
H19	0.8764	0.2611	0.3626	0.044*
C20	0.6864 (2)	0.3966 (3)	0.2384 (2)	0.0316 (5)
H20	0.7459	0.3662	0.2005	0.038*
C21	0.5698 (2)	0.2018 (3)	0.1704 (2)	0.0352 (6)
C22	0.4489 (2)	0.1337 (3)	0.1313 (3)	0.0457 (7)
H22A	0.4280	0.1056	0.1990	0.069*
H22B	0.4554	0.0621	0.0844	0.069*
H22C	0.3857	0.1895	0.0855	0.069*
C23	0.4851 (2)	0.5119 (3)	0.1630 (2)	0.0307 (5)
C24	0.4060 (2)	0.7251 (3)	0.1174 (2)	0.0371 (6)
C25	0.2952 (2)	0.8055 (3)	0.1067 (3)	0.0520 (8)
H25A	0.2616	0.8347	0.0271	0.078*
H25B	0.3190	0.8766	0.1587	0.078*
H25C	0.2340	0.7569	0.1275	0.078*
C26	1.0400 (3)	0.1360 (3)	0.5113 (3)	0.0692 (9)
H26A	1.0753	0.1935	0.4686	0.104*
H26B	0.9772	0.0863	0.4568	0.104*
H26C	1.1035	0.0814	0.5586	0.104*
N1	0.92957 (17)	0.8777 (2)	0.81336 (18)	0.0319 (5)
N2	1.03611 (17)	0.8057 (2)	0.8278 (2)	0.0339 (5)
N3	1.10017 (18)	0.5994 (2)	0.8432 (2)	0.0383 (5)
H3A	1.1689	0.6224	0.8336	0.046*
N4	0.57049 (17)	0.3249 (2)	0.1927 (2)	0.0332 (5)
N5	0.46128 (17)	0.3956 (2)	0.16790 (19)	0.0330 (5)
N6	0.39184 (18)	0.6002 (2)	0.1401 (2)	0.0357 (5)
H6A	0.3199	0.5754	0.1399	0.043*
O1	0.47967 (16)	0.7197 (2)	0.39944 (16)	0.0550 (5)
O2	0.83930 (16)	1.0588 (2)	0.8297 (2)	0.0525 (5)
O3	0.99404 (17)	0.4378 (2)	0.88764 (19)	0.0514 (5)
O4	0.98715 (18)	0.2046 (2)	0.58456 (19)	0.0676 (6)
O5	0.66898 (16)	0.1464 (2)	0.18601 (19)	0.0513 (5)
O6	0.50089 (16)	0.7653 (2)	0.10697 (18)	0.0487 (5)
S1	0.85560 (5)	0.64828 (6)	0.81229 (6)	0.03785 (17)
S2	0.63984 (5)	0.55696 (6)	0.18841 (6)	0.03857 (17)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0346 (10)	0.0384 (13)	0.0415 (13)	0.0002 (9)	0.0053 (10)	−0.0048 (10)
C2	0.0547 (16)	0.054 (2)	0.0347 (15)	−0.0045 (14)	0.0053 (13)	0.0004 (13)
C3	0.0597 (15)	0.0617 (19)	0.0407 (15)	−0.0191 (14)	0.0166 (12)	0.0057 (13)
C4	0.0404 (12)	0.0500 (15)	0.0426 (14)	−0.0140 (11)	0.0136 (11)	−0.0016 (12)
C5	0.0285 (10)	0.0297 (14)	0.0349 (13)	0.0004 (9)	0.0102 (10)	−0.0034 (11)
C6	0.0299 (9)	0.0337 (12)	0.0405 (12)	−0.0024 (8)	0.0099 (9)	−0.0001 (10)
C7	0.0236 (10)	0.0341 (14)	0.0378 (14)	−0.0022 (10)	0.0071 (10)	−0.0053 (12)
C8	0.0347 (12)	0.0371 (16)	0.0382 (15)	0.0007 (11)	0.0129 (11)	−0.0028 (12)
C9	0.0377 (12)	0.0392 (16)	0.0552 (18)	−0.0079 (13)	0.0142 (12)	−0.0115 (15)
C10	0.0253 (10)	0.0370 (16)	0.0324 (13)	−0.0024 (10)	0.0093 (9)	−0.0015 (11)
C11	0.0412 (13)	0.0371 (16)	0.0370 (15)	−0.0039 (12)	0.0096 (11)	−0.0004 (12)
C12	0.0521 (16)	0.0326 (16)	0.086 (2)	0.0014 (14)	0.0209 (16)	0.0069 (17)
C13	0.0384 (12)	0.0568 (17)	0.0667 (18)	−0.0103 (12)	0.0129 (12)	−0.0108 (15)
C14	0.0331 (10)	0.0456 (15)	0.0455 (14)	−0.0001 (10)	0.0048 (10)	0.0045 (11)
C15	0.0554 (16)	0.055 (2)	0.0351 (16)	−0.0062 (14)	0.0080 (13)	−0.0022 (13)
C16	0.0600 (15)	0.0552 (18)	0.0441 (15)	0.0019 (13)	0.0192 (13)	−0.0117 (13)
C17	0.0406 (11)	0.0386 (13)	0.0458 (14)	0.0050 (10)	0.0119 (11)	−0.0053 (11)
C18	0.0251 (10)	0.0291 (14)	0.0374 (14)	−0.0036 (9)	0.0066 (10)	−0.0007 (11)
C19	0.0301 (9)	0.0380 (12)	0.0417 (13)	0.0036 (9)	0.0118 (9)	0.0018 (11)
C20	0.0237 (10)	0.0339 (14)	0.0383 (14)	−0.0015 (10)	0.0112 (10)	−0.0012 (12)
C21	0.0325 (12)	0.0351 (15)	0.0398 (15)	−0.0032 (11)	0.0141 (10)	−0.0071 (12)
C22	0.0401 (13)	0.0432 (18)	0.0551 (18)	−0.0099 (13)	0.0167 (12)	−0.0118 (15)
C23	0.0268 (10)	0.0343 (15)	0.0289 (13)	−0.0005 (10)	0.0056 (9)	0.0035 (10)
C24	0.0371 (13)	0.0330 (15)	0.0358 (14)	−0.0013 (11)	0.0036 (11)	0.0008 (12)
C25	0.0428 (14)	0.0347 (16)	0.074 (2)	0.0065 (12)	0.0111 (14)	0.0046 (16)
C26	0.0557 (16)	0.066 (2)	0.088 (2)	0.0258 (16)	0.0253 (16)	0.0328 (19)
N1	0.0219 (9)	0.0343 (13)	0.0381 (12)	−0.0010 (8)	0.0074 (8)	−0.0054 (10)
N2	0.0238 (9)	0.0348 (13)	0.0425 (13)	0.0014 (9)	0.0096 (9)	−0.0019 (10)
N3	0.0308 (10)	0.0327 (13)	0.0541 (14)	−0.0009 (8)	0.0171 (9)	0.0045 (10)
N4	0.0234 (9)	0.0334 (13)	0.0407 (13)	−0.0005 (9)	0.0069 (8)	−0.0048 (10)
N5	0.0257 (9)	0.0332 (13)	0.0388 (12)	0.0007 (9)	0.0083 (8)	−0.0038 (10)
N6	0.0272 (9)	0.0322 (13)	0.0461 (12)	−0.0002 (8)	0.0089 (8)	0.0034 (10)
O1	0.0433 (9)	0.0665 (13)	0.0459 (10)	−0.0145 (9)	0.0006 (8)	−0.0070 (10)
O2	0.0383 (9)	0.0388 (12)	0.0845 (15)	0.0039 (10)	0.0252 (10)	−0.0079 (12)
O3	0.0465 (11)	0.0472 (14)	0.0617 (13)	−0.0102 (10)	0.0187 (10)	0.0077 (11)
O4	0.0572 (11)	0.0840 (16)	0.0567 (12)	0.0303 (11)	0.0110 (10)	0.0231 (12)
O5	0.0363 (9)	0.0405 (12)	0.0795 (14)	0.0048 (10)	0.0216 (9)	−0.0079 (12)
O6	0.0431 (10)	0.0430 (13)	0.0617 (13)	−0.0049 (9)	0.0187 (9)	0.0097 (11)
S1	0.0281 (3)	0.0403 (4)	0.0434 (4)	−0.0051 (3)	0.0087 (2)	0.0057 (3)
S2	0.0264 (3)	0.0371 (4)	0.0505 (4)	−0.0023 (3)	0.0096 (3)	0.0090 (3)

Geometric parameters (Å, º) top

C1—O1	1.359 (3)	C14—C19	1.377 (3)
C1—C6	1.374 (3)	C15—C16	1.374 (4)
C1—C2	1.384 (4)	C15—H15	0.9300
C2—C3	1.372 (4)	C16—C17	1.378 (4)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.380 (4)	C17—C18	1.378 (3)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.374 (3)	C18—C19	1.392 (3)
C4—H4	0.9300	C18—C20	1.499 (3)
C5—C6	1.394 (3)	C19—H19	0.9300
C5—C7	1.514 (4)	C20—N4	1.471 (3)
C6—H6	0.9300	C20—S2	1.824 (3)
C7—N1	1.456 (3)	C20—H20	0.9800
C7—S1	1.829 (3)	C21—O5	1.234 (3)
C7—H7	0.9800	C21—N4	1.332 (4)
C8—O2	1.215 (3)	C21—C22	1.493 (3)
C8—N1	1.345 (4)	C22—H22A	0.9600
C8—C9	1.486 (4)	C22—H22B	0.9600
C9—H9A	0.9600	C22—H22C	0.9600
C9—H9B	0.9600	C23—N5	1.267 (4)
C9—H9C	0.9600	C23—N6	1.377 (3)
C10—N2	1.274 (3)	C23—S2	1.757 (2)
C10—N3	1.375 (3)	C24—N6	1.370 (4)
C10—S1	1.753 (2)	C24—C25	1.493 (4)
C11—O3	1.215 (3)	C25—H25A	0.9600
C11—N3	1.373 (4)	C25—H25B	0.9600
C11—C12	1.492 (4)	C25—H25C	0.9600
C12—H12A	0.9600	C26—O4	1.410 (4)
C12—H12B	0.9600	C26—H26A	0.9600
C12—H12C	0.9600	C26—H26B	0.9600
C13—O1	1.416 (3)	C26—H26C	0.9600
C13—H13A	0.9600	N1—N2	1.397 (3)
C13—H13B	0.9600	N3—H3A	0.8600
C13—H13C	0.9600	N4—N5	1.401 (3)
C14—O4	1.364 (3)	N6—H6A	0.8600
C14—C15	1.373 (4)

O1—C1—C6	125.1 (2)	C16—C17—C18	119.6 (2)
O1—C1—C2	114.9 (2)	C16—C17—H17	120.2
C6—C1—C2	120.0 (2)	C18—C17—H17	120.2
C3—C2—C1	119.4 (3)	C17—C18—C19	119.6 (2)
C3—C2—H2	120.3	C17—C18—C20	121.3 (2)
C1—C2—H2	120.3	C19—C18—C20	119.0 (2)
C2—C3—C4	120.9 (3)	C14—C19—C18	120.0 (2)
C2—C3—H3	119.6	C14—C19—H19	120.0
C4—C3—H3	119.6	C18—C19—H19	120.0
C5—C4—C3	120.1 (2)	N4—C20—C18	111.4 (2)
C5—C4—H4	120.0	N4—C20—S2	103.01 (16)
C3—C4—H4	120.0	C18—C20—S2	114.9 (2)
C4—C5—C6	119.2 (2)	N4—C20—H20	109.1
C4—C5—C7	122.5 (2)	C18—C20—H20	109.1
C6—C5—C7	118.3 (2)	S2—C20—H20	109.1
C1—C6—C5	120.5 (2)	O5—C21—N4	119.2 (2)
C1—C6—H6	119.8	O5—C21—C22	121.8 (3)
C5—C6—H6	119.8	N4—C21—C22	118.9 (2)
N1—C7—C5	112.6 (2)	C21—C22—H22A	109.5
N1—C7—S1	102.46 (16)	C21—C22—H22B	109.5
C5—C7—S1	113.33 (19)	H22A—C22—H22B	109.5
N1—C7—H7	109.4	C21—C22—H22C	109.5
C5—C7—H7	109.4	H22A—C22—H22C	109.5
S1—C7—H7	109.4	H22B—C22—H22C	109.5
O2—C8—N1	119.7 (3)	N5—C23—N6	120.6 (2)
O2—C8—C9	122.5 (3)	N5—C23—S2	118.25 (19)
N1—C8—C9	117.7 (2)	N6—C23—S2	121.2 (2)
C8—C9—H9A	109.5	O6—C24—N6	121.8 (3)
C8—C9—H9B	109.5	O6—C24—C25	123.3 (3)
H9A—C9—H9B	109.5	N6—C24—C25	114.9 (2)
C8—C9—H9C	109.5	C24—C25—H25A	109.5
H9A—C9—H9C	109.5	C24—C25—H25B	109.5
H9B—C9—H9C	109.5	H25A—C25—H25B	109.5
N2—C10—N3	120.0 (2)	C24—C25—H25C	109.5
N2—C10—S1	118.12 (19)	H25A—C25—H25C	109.5
N3—C10—S1	121.8 (2)	H25B—C25—H25C	109.5
O3—C11—N3	120.9 (3)	O4—C26—H26A	109.5
O3—C11—C12	124.3 (3)	O4—C26—H26B	109.5
N3—C11—C12	114.8 (3)	H26A—C26—H26B	109.5
C11—C12—H12A	109.5	O4—C26—H26C	109.5
C11—C12—H12B	109.5	H26A—C26—H26C	109.5
H12A—C12—H12B	109.5	H26B—C26—H26C	109.5
C11—C12—H12C	109.5	C8—N1—N2	122.2 (2)
H12A—C12—H12C	109.5	C8—N1—C7	121.6 (2)
H12B—C12—H12C	109.5	N2—N1—C7	116.1 (2)
O1—C13—H13A	109.5	C10—N2—N1	109.3 (2)
O1—C13—H13B	109.5	C11—N3—C10	124.2 (2)
H13A—C13—H13B	109.5	C11—N3—H3A	117.9
O1—C13—H13C	109.5	C10—N3—H3A	117.9
H13A—C13—H13C	109.5	C21—N4—N5	122.2 (2)
H13B—C13—H13C	109.5	C21—N4—C20	122.0 (2)
O4—C14—C15	115.8 (2)	N5—N4—C20	115.8 (2)
O4—C14—C19	124.1 (2)	C23—N5—N4	110.0 (2)
C15—C14—C19	120.2 (2)	C24—N6—C23	124.4 (2)
C14—C15—C16	119.7 (3)	C24—N6—H6A	117.8
C14—C15—H15	120.1	C23—N6—H6A	117.8
C16—C15—H15	120.1	C1—O1—C13	117.9 (2)
C15—C16—C17	120.9 (3)	C14—O4—C26	118.5 (2)
C15—C16—H16	119.6	C10—S1—C7	88.3 (1)
C17—C16—H16	119.6	C23—S2—C20	88.6 (1)

O1—C1—C2—C3	−179.1 (3)	N3—C10—N2—N1	179.8 (2)
C6—C1—C2—C3	0.8 (4)	S1—C10—N2—N1	1.3 (3)
C1—C2—C3—C4	−0.1 (5)	C8—N1—N2—C10	162.3 (3)
C2—C3—C4—C5	0.5 (5)	C7—N1—N2—C10	−18.8 (3)
C3—C4—C5—C6	−1.4 (4)	O3—C11—N3—C10	−1.5 (4)
C3—C4—C5—C7	−179.6 (3)	C12—C11—N3—C10	178.4 (3)
O1—C1—C6—C5	178.2 (2)	N2—C10—N3—C11	166.0 (3)
C2—C1—C6—C5	−1.8 (4)	S1—C10—N3—C11	−15.5 (4)
C4—C5—C6—C1	2.1 (4)	O5—C21—N4—N5	174.7 (2)
C7—C5—C6—C1	−179.6 (2)	C22—C21—N4—N5	−7.5 (4)
C4—C5—C7—N1	−2.5 (4)	O5—C21—N4—C20	−1.6 (4)
C6—C5—C7—N1	179.3 (2)	C22—C21—N4—C20	176.2 (2)
C4—C5—C7—S1	−118.2 (2)	C18—C20—N4—C21	−81.9 (3)
C6—C5—C7—S1	63.5 (3)	S2—C20—N4—C21	154.4 (2)
O4—C14—C15—C16	−178.6 (3)	C18—C20—N4—N5	101.6 (3)
C19—C14—C15—C16	1.1 (4)	S2—C20—N4—N5	−22.2 (3)
C14—C15—C16—C17	−1.1 (5)	N6—C23—N5—N4	−179.8 (2)
C15—C16—C17—C18	0.8 (4)	S2—C23—N5—N4	−0.8 (3)
C16—C17—C18—C19	−0.4 (4)	C21—N4—N5—C23	−160.5 (3)
C16—C17—C18—C20	177.1 (3)	C20—N4—N5—C23	16.0 (3)
O4—C14—C19—C18	179.0 (2)	O6—C24—N6—C23	5.9 (4)
C15—C14—C19—C18	−0.7 (4)	C25—C24—N6—C23	−174.3 (2)
C17—C18—C19—C14	0.4 (4)	N5—C23—N6—C24	−170.8 (3)
C20—C18—C19—C14	−177.2 (2)	S2—C23—N6—C24	10.3 (4)
C17—C18—C20—N4	−74.4 (3)	C6—C1—O1—C13	0.0 (4)
C19—C18—C20—N4	103.1 (2)	C2—C1—O1—C13	180.0 (2)
C17—C18—C20—S2	42.2 (3)	C15—C14—O4—C26	177.9 (3)
C19—C18—C20—S2	−140.2 (2)	C19—C14—O4—C26	−1.8 (4)
O2—C8—N1—N2	−176.4 (2)	N2—C10—S1—C7	11.6 (2)
C9—C8—N1—N2	6.0 (4)	N3—C10—S1—C7	−166.9 (2)
O2—C8—N1—C7	4.7 (4)	N1—C7—S1—C10	−18.96 (18)
C9—C8—N1—C7	−172.9 (2)	C5—C7—S1—C10	102.70 (18)
C5—C7—N1—C8	82.3 (3)	N5—C23—S2—C20	−10.6 (2)
S1—C7—N1—C8	−155.5 (2)	N6—C23—S2—C20	168.4 (2)
C5—C7—N1—N2	−96.6 (3)	N4—C20—S2—C23	16.77 (18)
S1—C7—N1—N2	25.5 (3)	C18—C20—S2—C23	−104.62 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O5ⁱ	0.86	1.95	2.801 (3)	171
N6—H6A···O2ⁱⁱ	0.86	1.96	2.799 (3)	164
C25—H25C···O2ⁱⁱ	0.96	2.37	3.238 (4)	150

Symmetry codes: (i) −x+2, y+1/2, −z+1; (ii) −x+1, y−1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₅N₃O₃S
M_r	293.34
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	11.3790 (4), 10.5993 (3), 11.9596 (2)
β (°)	108.225 (2)
V (Å³)	1370.08 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.30 × 0.20 × 0.16

Data collection
Diffractometer	Bruker Kappa-APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1999)
T_min, T_max	0.930, 0.962
No. of measured, independent and observed [I > 2σ(I)] reflections	16660, 7595, 5635
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.695

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.109, 1.03
No. of reflections	7595
No. of parameters	367
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.25
Absolute structure	Flack (1983), with 3584 Friedel pairs
Absolute structure parameter	0.07 (7)

Computer programs: , APEX2 (Bruker, 2004) and SAINT (Bruker, 2004), SAINT (Bruker, 2004) and XPREP (Bruker, 2004), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O5ⁱ	0.86	1.95	2.801 (3)	171
N6—H6A···O2ⁱⁱ	0.86	1.96	2.799 (3)	164
C25—H25C···O2ⁱⁱ	0.96	2.37	3.238 (4)	150

Symmetry codes: (i) −x+2, y+1/2, −z+1; (ii) −x+1, y−1/2, −z+1.

Acknowledgements

This research work was supported by the second stage of the BK21 Program, Republic of Korea. DV acknowledges financial support from the University Grants Commission (UGC-SAP) and the Department of Science and Technology (DST-FIST), Government of India, for providing facilities.

References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343–350. CrossRef Web of Science IUCr Journals Google Scholar
Balasubramanian, S., Ramalingan, C., Aridoss, G., Parthiban, S. & Kabilan, S. (2004). Med. Chem. Res. 13(5), 297–311. Web of Science CrossRef Google Scholar
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Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Li, Z., Wang, X. & Da, Y. (2001). Synth. Commun. 31, 1829–1936. Web of Science CrossRef CAS Google Scholar
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Radwan, M. A. A., Ragab, E. A., Sabry, N. M. & El-Shenawy, S. M. (2007). Bioorg. Med. Chem. 15, 3832–3841. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Supuran, C. T., Briganti, F., Tilli, S., Chegwidden, W. R. & Scozzafava, A. (2001). Bioorg. Med. Chem. 9, 703–714. Web of Science CrossRef PubMed CAS Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

N-[4-Acetyl-5-(3-meth­oxy­phen­yl)-4,5-di­hydro-1,3,4-thia­diazol-2-yl]acetamide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N-[4-Acetyl-5-(3-methoxyphenyl)-4,5-dihydro-1,3,4-thiadiazol-2-yl]acetamide