2-(2-Methyl­phen­yl)-N-(1,3-thia­zol-2-yl)acetamide

Abstract

In the title compound, C₁₂H₁₂N₂OS, the dihedral angle between the benzene and thia­zole rings is 83.5 (7)°. The acetamide group is almost coplanar with the thia­zole ring, being twisted from it by 4.2 (9)°. In the crystal, pairs of N—H⋯N hydrogen bonds link mol­ecules into inversion dimers, generating R ₂ ²[8] loops; the dimers are stacked along [001].

Related literature  

For the structural similarity of N-substituted 2-aryl­acetamides to the lateral chain of benzyl­penicillin, see: Mijin et al. (2008 ▶). For our studies of acetamides, see: Nayak et al. (2014 ▶).

Experimental  

Crystal data  

• C₁₂H₁₂N₂OS

• M _r = 232.30

• Monoclinic,

• a = 17.6983 (6) Å

• b = 4.94078 (13) Å

• c = 14.4603 (5) Å

• β = 111.236 (4)°

• V = 1178.60 (7) ų

• Z = 4

• Cu Kα radiation

• μ = 2.28 mm⁻¹

• T = 173 K

• 0.38 × 0.26 × 0.14 mm

Data collection  

• Agilent Agilent (Eos, Gemini) diffractometer

• Absorption correction: multi-scan (CrysAlis RED; Agilent, 2012 ▶) T _min = 0.582, T _max = 1.000

• 7059 measured reflections

• 2250 independent reflections

• 2065 reflections with I > 2σ(I)

• R _int = 0.037

Refinement  

• R[F ² > 2σ(F ²)] = 0.040

• wR(F ²) = 0.113

• S = 1.07

• 2250 reflections

• 147 parameters

• H-atom parameters constrained

• Δρ_max = 0.30 e Å⁻³

• Δρ_min = −0.28 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012 ▶); program(s) used to solve structure: SUPERFLIP (Palatinus et al., 2012 ▶); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Supplementary Material

CCDC reference: 1004337

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N2i	0.88	2.04	2.9138 (19)	176

Symmetry code: (i) .

supplementary crystallographic information

1. Comment

N-Substituted 2-arylacetamides are interesting compounds because of their structural similarity to the lateral chain of natural benzylpenicillin (Mijin et al., 2008). As part of our ongoing studies of such systems (Nayak et al., 2014) we report herein the crystal structure of the title compound, (I), C₁₂H₁₂N₂OS.

In (I), the dihedral angle between the mean planes of the phenyl and thiazol rings is 83.5 (7)° (Fig. 1). The acetamide group (N1/O1/C4/C5) is close to coplanar with the mean plane of the thiazol ring twisted by 4.2 (9)°. In the crystal, pairs of N—H···N hydrogen bonds link the molecules into inversion dimers forming R₂²[8] ring motifs and stacked along [001] (Fig. 2).

2. Experimental

2-Methylphenylacetic acid (0.150 g, 1 mmol), 2-aminothiazole (0.100 g, 1 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (1.0 g, 0.01 mol) were dissolved in dichloromethane (20 ml). The mixture was stirred in presence of triethylamine at 273 K for about 3 h. The contents were poured into 100 ml of ice-cold aqueous hydrochloric acid with stirring, which was extracted thrice with dichloromethane. The organic layer was washed with saturated NaHCO₃ solution and brine solution, dried and concentrated under reduced pressure to give the title compound (I). Colourless prisms were grown from methanol solution by slow evaporation (M.P.: 401–403 K).

3. Refinement

All of the H atoms were placed in their calculated positions and then refined using the riding model with Atom—H lengths of 0.95Å (CH), 0.99Å (CH₂), 0.98Å (CH₃) or 0.88Å (NH). Isotropic displacement parameters for these atoms were set to 1.2 (CH, CH₂, NH) or 1.5 (CH₃) times U_eq of the parent atom. Idealised Me refined as rotating group.

Figures

Fig. 1.

ORTEP drawing of (I), C12H12N2OS, showing 30% probability displacement ellipsoids.

Fig. 2.

Molecular packing for (I) viewed along the b axis. Dashed lines indicate weak N1—H1···N2 hydrogen bonds forming inversion dimers in an R22[8] motif format and stacked along [001]. H atoms not involved in hydrogen bonding have been removed for clarity.

Fig. 3.

Reaction scheme.

Crystal data

C12H12N2OS	F(000) = 488
Mr = 232.30	Dx = 1.309 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 17.6983 (6) Å	Cell parameters from 3416 reflections
b = 4.94078 (13) Å	θ = 3.4–71.5°
c = 14.4603 (5) Å	µ = 2.28 mm−1
β = 111.236 (4)°	T = 173 K
V = 1178.60 (7) Å3	Prism, colourless
Z = 4	0.38 × 0.26 × 0.14 mm

Data collection

Agilent Agilent (Eos, Gemini) diffractometer	2250 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2065 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
Detector resolution: 16.0416 pixels mm-1	θmax = 71.3°, θmin = 5.4°
ω scans	h = −12→21
Absorption correction: multi-scan (CrysAlis RED; Agilent, 2012)	k = −5→6
Tmin = 0.582, Tmax = 1.000	l = −17→16
7059 measured reflections

Refinement

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.040	w = 1/[σ2(Fo2) + (0.0678P)2 + 0.367P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.113	(Δ/σ)max = 0.001
S = 1.07	Δρmax = 0.30 e Å−3
2250 reflections	Δρmin = −0.28 e Å−3
147 parameters	Extinction correction: SHELXL2012 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.0013 (5)
Primary atom site location: structure-invariant direct methods

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.51096 (2)	1.09810 (8)	0.33600 (3)	0.02349 (18)
O1	0.66917 (7)	0.9640 (3)	0.43484 (10)	0.0341 (3)
N1	0.58012 (8)	0.6996 (3)	0.47251 (10)	0.0225 (3)
H1	0.5748	0.5659	0.5099	0.027*
N2	0.43898 (8)	0.7241 (3)	0.39749 (10)	0.0241 (3)
C1	0.51059 (10)	0.8180 (3)	0.40772 (11)	0.0204 (3)
C2	0.38010 (11)	0.8760 (3)	0.32755 (13)	0.0269 (4)
H2	0.3240	0.8362	0.3089	0.032*
C3	0.40679 (11)	1.0842 (3)	0.28727 (13)	0.0263 (4)
H3	0.3730	1.2055	0.2390	0.032*
C4	0.65649 (10)	0.7763 (3)	0.48226 (12)	0.0248 (4)
C5	0.72262 (11)	0.6059 (4)	0.55603 (14)	0.0311 (4)
H5A	0.7121	0.5926	0.6186	0.037*
H5B	0.7205	0.4206	0.5291	0.037*
C6	0.80617 (11)	0.7206 (4)	0.57813 (14)	0.0352 (4)
C7	0.85116 (13)	0.6620 (5)	0.51962 (17)	0.0469 (5)
C8	0.92758 (14)	0.7817 (6)	0.5445 (2)	0.0675 (9)
H8	0.9594	0.7420	0.5055	0.081*
C9	0.95774 (17)	0.9541 (7)	0.6231 (3)	0.0828 (11)
H9	1.0096	1.0343	0.6377	0.099*
C10	0.91323 (19)	1.0119 (7)	0.6813 (3)	0.0811 (10)
H10	0.9339	1.1318	0.7361	0.097*
C11	0.83836 (15)	0.8938 (5)	0.6590 (2)	0.0559 (6)
H11	0.8079	0.9311	0.6998	0.067*
C12	0.81906 (19)	0.4717 (7)	0.4331 (2)	0.0710 (8)
H12A	0.8022	0.3021	0.4550	0.106*
H12B	0.8616	0.4343	0.4064	0.106*
H12C	0.7724	0.5546	0.3814	0.106*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
S1	0.0313 (3)	0.0181 (3)	0.0218 (2)	−0.00228 (14)	0.01054 (18)	0.00177 (13)
O1	0.0295 (7)	0.0335 (7)	0.0382 (7)	−0.0062 (5)	0.0106 (5)	0.0106 (6)
N1	0.0257 (7)	0.0202 (7)	0.0220 (6)	−0.0031 (5)	0.0089 (5)	0.0035 (5)
N2	0.0257 (7)	0.0219 (7)	0.0250 (7)	−0.0004 (5)	0.0096 (5)	0.0022 (5)
C1	0.0294 (8)	0.0159 (7)	0.0183 (7)	−0.0018 (6)	0.0115 (6)	−0.0023 (6)
C2	0.0260 (8)	0.0261 (9)	0.0284 (8)	0.0015 (6)	0.0096 (7)	0.0019 (6)
C3	0.0308 (9)	0.0247 (9)	0.0235 (8)	0.0044 (6)	0.0101 (7)	0.0013 (6)
C4	0.0265 (8)	0.0240 (9)	0.0233 (8)	−0.0034 (6)	0.0085 (7)	−0.0018 (6)
C5	0.0271 (9)	0.0322 (10)	0.0335 (9)	−0.0013 (7)	0.0102 (7)	0.0068 (7)
C6	0.0263 (9)	0.0361 (11)	0.0391 (10)	0.0002 (7)	0.0070 (7)	0.0099 (8)
C7	0.0370 (11)	0.0567 (13)	0.0489 (12)	0.0071 (10)	0.0178 (10)	0.0186 (10)
C8	0.0339 (12)	0.089 (2)	0.0833 (19)	0.0044 (13)	0.0251 (13)	0.0412 (17)
C9	0.0353 (13)	0.090 (2)	0.101 (3)	−0.0176 (14)	−0.0016 (15)	0.037 (2)
C10	0.0568 (17)	0.071 (2)	0.083 (2)	−0.0188 (15)	−0.0131 (15)	−0.0067 (17)
C11	0.0426 (12)	0.0610 (16)	0.0519 (14)	0.0004 (10)	0.0026 (10)	−0.0077 (11)
C12	0.0721 (18)	0.088 (2)	0.0601 (16)	0.0142 (16)	0.0329 (14)	−0.0043 (15)

Geometric parameters (Å, º)

S1—C1	1.7307 (16)	C6—C7	1.386 (3)
S1—C3	1.7202 (18)	C6—C11	1.394 (3)
O1—C4	1.222 (2)	C7—C8	1.399 (3)
N1—H1	0.8800	C7—C12	1.502 (4)
N1—C1	1.378 (2)	C8—H8	0.9500
N1—C4	1.361 (2)	C8—C9	1.365 (5)
N2—C1	1.307 (2)	C9—H9	0.9500
N2—C2	1.382 (2)	C9—C10	1.375 (5)
C2—H2	0.9500	C10—H10	0.9500
C2—C3	1.349 (2)	C10—C11	1.375 (4)
C3—H3	0.9500	C11—H11	0.9500
C4—C5	1.521 (2)	C12—H12A	0.9800
C5—H5A	0.9900	C12—H12B	0.9800
C5—H5B	0.9900	C12—H12C	0.9800
C5—C6	1.506 (2)
C3—S1—C1	88.70 (8)	C7—C6—C11	119.3 (2)
C1—N1—H1	117.9	C11—C6—C5	118.73 (19)
C4—N1—H1	117.9	C6—C7—C8	118.1 (3)
C4—N1—C1	124.11 (14)	C6—C7—C12	120.8 (2)
C1—N2—C2	109.46 (14)	C8—C7—C12	121.2 (2)
N1—C1—S1	123.41 (12)	C7—C8—H8	119.1
N2—C1—S1	115.48 (12)	C9—C8—C7	121.8 (3)
N2—C1—N1	121.11 (14)	C9—C8—H8	119.1
N2—C2—H2	121.9	C8—C9—H9	120.0
C3—C2—N2	116.18 (16)	C8—C9—C10	120.1 (3)
C3—C2—H2	121.9	C10—C9—H9	120.0
S1—C3—H3	124.9	C9—C10—H10	120.5
C2—C3—S1	110.15 (13)	C9—C10—C11	119.1 (3)
C2—C3—H3	124.9	C11—C10—H10	120.5
O1—C4—N1	122.06 (15)	C6—C11—H11	119.2
O1—C4—C5	124.26 (15)	C10—C11—C6	121.5 (3)
N1—C4—C5	113.67 (14)	C10—C11—H11	119.2
C4—C5—H5A	109.0	C7—C12—H12A	109.5
C4—C5—H5B	109.0	C7—C12—H12B	109.5
H5A—C5—H5B	107.8	C7—C12—H12C	109.5
C6—C5—C4	112.79 (14)	H12A—C12—H12B	109.5
C6—C5—H5A	109.0	H12A—C12—H12C	109.5
C6—C5—H5B	109.0	H12B—C12—H12C	109.5
C7—C6—C5	121.9 (2)
O1—C4—C5—C6	9.8 (3)	C4—C5—C6—C7	−86.3 (2)
N1—C4—C5—C6	−170.71 (15)	C4—C5—C6—C11	92.8 (2)
N2—C2—C3—S1	0.6 (2)	C5—C6—C7—C8	178.75 (19)
C1—S1—C3—C2	0.12 (13)	C5—C6—C7—C12	−2.2 (3)
C1—N1—C4—O1	1.8 (3)	C5—C6—C11—C10	−177.9 (2)
C1—N1—C4—C5	−177.74 (14)	C6—C7—C8—C9	−0.7 (4)
C1—N2—C2—C3	−1.3 (2)	C7—C6—C11—C10	1.1 (4)
C2—N2—C1—S1	1.36 (17)	C7—C8—C9—C10	0.8 (5)
C2—N2—C1—N1	−179.21 (14)	C8—C9—C10—C11	0.0 (5)
C3—S1—C1—N1	179.70 (14)	C9—C10—C11—C6	−1.0 (5)
C3—S1—C1—N2	−0.89 (13)	C11—C6—C7—C8	−0.3 (3)
C4—N1—C1—S1	−4.9 (2)	C11—C6—C7—C12	178.7 (2)
C4—N1—C1—N2	175.74 (14)	C12—C7—C8—C9	−179.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2i	0.88	2.04	2.9138 (19)	176

Symmetry code: (i) −x+1, −y+1, −z+1.