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

Narayana, B.; Nayak, P.S.; Sarojini, B.K.; Jasinski, J.P.

doi:10.1107/S1600536814011684

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 70| Part 6| June 2014| Page o716

doi:10.1107/S1600536814011684

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

B. Narayana,^a Prakash S. Nayak,^a Balladka K. Sarojini ^b and Jerry P. Jasinski ^c ^*

^aDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, ^bDepartment of Studies in Chemistry, Industrial Chemistry Section, Mangalore University, Mangalagangotri 574 199, India, and ^cDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA
^*Correspondence e-mail: jjasinski@keene.edu

(Received 19 May 2014; accepted 20 May 2014; online 31 May 2014)

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 R₂²[8] loops; the dimers are stacked along [001].

CCDC reference: 1004337

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, P 2₁ /c
a = 17.6983 (6) Å
b = 4.94078 (13) Å
c = 14.4603 (5) Å
β = 111.236 (4)°
V = 1178.60 (7) Å³
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[F² > 2σ(F²)] = 0.040
wR(F²) = 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

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) -x+1, -y+1, -z+1.

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.

Supporting information

CCDC reference: 1004337

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814011684/hb7232sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814011684/hb7232Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814011684/hb7232Isup3.cml

checkCIF report

Comment top

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).

Related literature top

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 top

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).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); 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 (Dolomanov et al., 2009).

Figures top

	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.

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

Crystal data top

C₁₂H₁₂N₂OS	F(000) = 488
M_r = 232.30	D_x = 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 top

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

Refinement top

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(F_o²) + (0.0678P)² + 0.367P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.113	(Δ/σ)_max = 0.001
S = 1.07	Δρ_max = 0.30 e Å⁻³
2250 reflections	Δρ_min = −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

Crystal data top

C₁₂H₁₂N₂OS	V = 1178.60 (7) Å³
M_r = 232.30	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 17.6983 (6) Å	µ = 2.28 mm⁻¹
b = 4.94078 (13) Å	T = 173 K
c = 14.4603 (5) Å	0.38 × 0.26 × 0.14 mm
β = 111.236 (4)°

Data collection top

Agilent Agilent (Eos, Gemini) diffractometer	2250 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Agilent, 2012)	2065 reflections with I > 2σ(I)
T_min = 0.582, T_max = 1.000	R_int = 0.037
7059 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.113	H-atom parameters constrained
S = 1.07	Δρ_max = 0.30 e Å⁻³
2250 reflections	Δρ_min = −0.28 e Å⁻³
147 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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) top

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) top

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.

Hydrogen-bond geometry (Å, º) top

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.

Acknowledgements

BN thanks the UGC for financial assistance through BSR one-time grant for the purchase of chemicals. PSN thanks Mangalore University for research facilities and the DST–PURSE financial assistance. JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

References

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