N-(1,3-Thia­zol-2-yl)-2-(2,4,6-trimethyl­phen­yl)acetamide

Fun, H.-K.; Quah, C.K.; Nayak, P.S.; Narayana, B.; Sarojini, B.K.

doi:10.1107/S1600536812031595

organic compounds

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ISSN: 2056-9890

Volume 68| Part 8| August 2012| Page o2461

https://doi.org/10.1107/S1600536812031595

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N-(1,3-Thiazol-2-yl)-2-(2,4,6-trimethylphenyl)acetamide

Hoong-Kun Fun,^a ^*‡ Ching Kheng Quah,^a § Prakash S. Nayak,^b B. Narayana ^b and B. K. Sarojini ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and ^cDepartment of Chemistry, P. A. College of Engineering, Nadupadavu, Mangalore 574 153, India
^*Correspondence e-mail: hkfun@usm.my

(Received 8 July 2012; accepted 11 July 2012; online 18 July 2012)

In the title compound, C₁₄H₁₆N₂OS, the thiazole ring is essentially planar (r.m.s. deviation = 0.005 Å) and it forms a dihedral angle of 75.21 (8)° with the benzene ring. In the crystal, molecules are linked into inversion dimers by pairs of N—H⋯N hydrogen bonds to generate R₂²(8) loops.

Related literature

For general background to and related structures of the title compound, see: Fun et al. (2011a ,b , 2012 ). For graph-set notation of hydrogen bonds, see: Bernstein et al. (1995 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₄H₁₆N₂OS
M_r = 260.35
Monoclinic, P 2₁ /c
a = 16.421 (2) Å
b = 4.6397 (7) Å
c = 20.1144 (18) Å
β = 123.150 (7)°
V = 1283.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 100 K
0.30 × 0.25 × 0.09 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.932, T_max = 0.979
13735 measured reflections
3748 independent reflections
2999 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.103
S = 1.03
3748 reflections
166 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1⋯N1ⁱ	0.88	2.08	2.9623 (19)	175
Symmetry code: (i) -x+2, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812031595/hb6891sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812031595/hb6891Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812031595/hb6891Isup3.cml

checkCIF report

Comment top

In continuation of our work on synthesis of amides (Fun et al., 2011a,b, 2012), we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the thiazol-2-yl ring (S1/N1/C1–C3) is essentially planar (r.m.s. deviation = 0.005 Å) and it forms a dihedral angle of 75.21 (8)° with the benzene ring (C6–C11). Bond lengths and angles are comparable to those in related structures (Fun et al., 2011a,b, 2012).

In the crystal (Fig. 2), molecules are linked into an inversion dimer by pairs of intermolecular N2—H1···N1 hydrogen bonds (Table 1).

Related literature top

For general background to and related structures of the title compound, see: Fun et al. (2011a,b, 2012). For graph-set notation of hydrogen bonds, see: Bernstein et al. (1995). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

2,4,6-Trimethylphenylacetic acid (0.178 g, 1 mmol), 2-aminothiazole (0.1 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. Organic layer was washed with saturated NaHCO₃ solution and brine solution, dried and concentrated under reduced pressure to give the title compound. Colourless blocks were grown from an acetone and toluene (1:1) solvent mixture by the slow evaporation method (m.p. 457–459 K).

Structure description top

In continuation of our work on synthesis of amides (Fun et al., 2011a,b, 2012), we report herein the crystal structure of the title compound.

In the crystal (Fig. 2), molecules are linked into an inversion dimer by pairs of intermolecular N2—H1···N1 hydrogen bonds (Table 1).

For general background to and related structures of the title compound, see: Fun et al. (2011a,b, 2012). For graph-set notation of hydrogen bonds, see: Bernstein et al. (1995). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound showing 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The crystal structure of the title compound, viewed along the b axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.

N-(1,3-Thiazol-2-yl)-2-(2,4,6-trimethylphenyl)acetamide top

Crystal data top

C₁₄H₁₆N₂OS	F(000) = 552
M_r = 260.35	D_x = 1.348 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4087 reflections
a = 16.421 (2) Å	θ = 3.0–29.9°
b = 4.6397 (7) Å	µ = 0.24 mm⁻¹
c = 20.1144 (18) Å	T = 100 K
β = 123.150 (7)°	Block, colourless
V = 1283.1 (3) Å³	0.30 × 0.25 × 0.09 mm
Z = 4

Data collection top

Bruker SMART APEXII DUO CCD diffractometer	3748 independent reflections
Radiation source: fine-focus sealed tube	2999 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
φ and ω scans	θ_max = 30.1°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −23→20
T_min = 0.932, T_max = 0.979	k = −6→6
13735 measured reflections	l = −26→28

Refinement top

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.103	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0444P)² + 0.7659P] where P = (F_o² + 2F_c²)/3
3748 reflections	(Δ/σ)_max = 0.001
166 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.51 e Å⁻³

Crystal data top

C₁₄H₁₆N₂OS	V = 1283.1 (3) Å³
M_r = 260.35	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.421 (2) Å	µ = 0.24 mm⁻¹
b = 4.6397 (7) Å	T = 100 K
c = 20.1144 (18) Å	0.30 × 0.25 × 0.09 mm
β = 123.150 (7)°

Data collection top

Bruker SMART APEXII DUO CCD diffractometer	3748 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2999 reflections with I > 2σ(I)
T_min = 0.932, T_max = 0.979	R_int = 0.040
13735 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.103	H-atom parameters constrained
S = 1.03	Δρ_max = 0.39 e Å⁻³
3748 reflections	Δρ_min = −0.51 e Å⁻³
166 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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.

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 > 2sigma(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
S1	1.03056 (3)	0.78584 (8)	0.83439 (2)	0.01686 (10)
O1	0.86995 (7)	0.4661 (2)	0.75301 (6)	0.0180 (2)
N1	1.06903 (9)	0.7448 (3)	0.97704 (7)	0.0176 (2)
N2	0.93660 (8)	0.4568 (3)	0.88579 (7)	0.0151 (2)
H1	0.9347	0.3871	0.9256	0.018*
C1	1.13491 (11)	0.9354 (3)	0.97864 (9)	0.0206 (3)
H1A	1.1835	1.0281	1.0262	0.025*
C2	1.12628 (11)	0.9823 (3)	0.90878 (9)	0.0203 (3)
H2A	1.1671	1.1057	0.9017	0.024*
C3	1.01013 (10)	0.6518 (3)	0.90413 (8)	0.0145 (3)
C4	0.86909 (10)	0.3723 (3)	0.80944 (8)	0.0146 (3)
C5	0.79327 (10)	0.1587 (3)	0.79947 (8)	0.0166 (3)
H5A	0.7985	0.1370	0.8506	0.020*
H5B	0.8060	−0.0318	0.7847	0.020*
C6	0.69101 (10)	0.2559 (3)	0.73607 (8)	0.0153 (3)
C7	0.64731 (10)	0.1640 (3)	0.65713 (8)	0.0158 (3)
C8	0.55387 (10)	0.2626 (3)	0.60037 (9)	0.0184 (3)
H8A	0.5238	0.1988	0.5471	0.022*
C9	0.50331 (11)	0.4500 (3)	0.61885 (9)	0.0201 (3)
C10	0.54813 (11)	0.5407 (3)	0.69713 (9)	0.0211 (3)
H10A	0.5147	0.6698	0.7109	0.025*
C11	0.64099 (11)	0.4466 (3)	0.75590 (9)	0.0180 (3)
C12	0.69872 (11)	−0.0344 (3)	0.63240 (9)	0.0209 (3)
H12A	0.6596	−0.0557	0.5745	0.031*
H12B	0.7076	−0.2234	0.6572	0.031*
H12C	0.7623	0.0469	0.6494	0.031*
C13	0.40305 (12)	0.5556 (4)	0.55574 (10)	0.0287 (4)
H13A	0.3996	0.7646	0.5607	0.043*
H13B	0.3546	0.4608	0.5624	0.043*
H13C	0.3899	0.5098	0.5032	0.043*
C14	0.68632 (12)	0.5548 (4)	0.83981 (9)	0.0251 (3)
H14A	0.6451	0.7057	0.8406	0.038*
H14B	0.7509	0.6340	0.8592	0.038*
H14C	0.6923	0.3951	0.8741	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01899 (17)	0.02010 (18)	0.01301 (16)	−0.00305 (13)	0.00974 (14)	0.00054 (13)
O1	0.0200 (5)	0.0210 (5)	0.0134 (5)	−0.0015 (4)	0.0094 (4)	0.0009 (4)
N1	0.0188 (6)	0.0209 (6)	0.0125 (5)	−0.0052 (5)	0.0083 (5)	−0.0013 (4)
N2	0.0174 (6)	0.0170 (6)	0.0114 (5)	−0.0037 (4)	0.0082 (5)	−0.0004 (4)
C1	0.0201 (7)	0.0230 (8)	0.0167 (7)	−0.0076 (6)	0.0087 (6)	−0.0021 (6)
C2	0.0192 (7)	0.0230 (7)	0.0183 (7)	−0.0054 (6)	0.0099 (6)	0.0001 (6)
C3	0.0164 (6)	0.0145 (6)	0.0136 (6)	0.0002 (5)	0.0089 (5)	0.0007 (5)
C4	0.0160 (6)	0.0134 (6)	0.0139 (6)	0.0019 (5)	0.0077 (5)	0.0002 (5)
C5	0.0185 (7)	0.0151 (7)	0.0144 (6)	−0.0022 (5)	0.0079 (5)	0.0004 (5)
C6	0.0169 (6)	0.0133 (6)	0.0161 (6)	−0.0020 (5)	0.0092 (5)	0.0002 (5)
C7	0.0182 (6)	0.0125 (6)	0.0168 (6)	−0.0024 (5)	0.0097 (6)	−0.0009 (5)
C8	0.0181 (7)	0.0188 (7)	0.0155 (7)	−0.0037 (5)	0.0074 (6)	−0.0013 (5)
C9	0.0176 (7)	0.0211 (7)	0.0221 (7)	0.0000 (5)	0.0111 (6)	0.0034 (6)
C10	0.0217 (7)	0.0220 (8)	0.0240 (8)	0.0012 (6)	0.0155 (6)	0.0001 (6)
C11	0.0210 (7)	0.0176 (7)	0.0186 (7)	−0.0032 (5)	0.0130 (6)	−0.0020 (5)
C12	0.0245 (7)	0.0178 (7)	0.0169 (7)	0.0015 (6)	0.0091 (6)	−0.0020 (5)
C13	0.0211 (8)	0.0375 (10)	0.0267 (8)	0.0061 (7)	0.0125 (7)	0.0083 (7)
C14	0.0294 (8)	0.0288 (9)	0.0211 (8)	−0.0019 (7)	0.0164 (7)	−0.0051 (6)

Geometric parameters (Å, º) top

S1—C2	1.7227 (16)	C7—C12	1.506 (2)
S1—C3	1.7267 (14)	C8—C9	1.386 (2)
O1—C4	1.2230 (17)	C8—H8A	0.9500
N1—C3	1.3119 (18)	C9—C10	1.389 (2)
N1—C1	1.3840 (19)	C9—C13	1.509 (2)
N2—C4	1.3709 (18)	C10—C11	1.394 (2)
N2—C3	1.3875 (18)	C10—H10A	0.9500
N2—H1	0.8794	C11—C14	1.510 (2)
C1—C2	1.351 (2)	C12—H12A	0.9800
C1—H1A	0.9500	C12—H12B	0.9800
C2—H2A	0.9500	C12—H12C	0.9800
C4—C5	1.516 (2)	C13—H13A	0.9800
C5—C6	1.519 (2)	C13—H13B	0.9800
C5—H5A	0.9900	C13—H13C	0.9800
C5—H5B	0.9900	C14—H14A	0.9800
C6—C7	1.404 (2)	C14—H14B	0.9800
C6—C11	1.405 (2)	C14—H14C	0.9800
C7—C8	1.397 (2)

C2—S1—C3	88.58 (7)	C9—C8—H8A	118.7
C3—N1—C1	108.98 (12)	C7—C8—H8A	118.7
C4—N2—C3	122.51 (12)	C8—C9—C10	118.04 (14)
C4—N2—H1	120.3	C8—C9—C13	121.07 (14)
C3—N2—H1	117.2	C10—C9—C13	120.89 (15)
C2—C1—N1	116.28 (14)	C9—C10—C11	121.49 (14)
C2—C1—H1A	121.9	C9—C10—H10A	119.3
N1—C1—H1A	121.9	C11—C10—H10A	119.3
C1—C2—S1	110.20 (11)	C10—C11—C6	119.66 (13)
C1—C2—H2A	124.9	C10—C11—C14	119.06 (14)
S1—C2—H2A	124.9	C6—C11—C14	121.28 (14)
N1—C3—N2	120.93 (12)	C7—C12—H12A	109.5
N1—C3—S1	115.96 (11)	C7—C12—H12B	109.5
N2—C3—S1	123.11 (10)	H12A—C12—H12B	109.5
O1—C4—N2	121.68 (13)	C7—C12—H12C	109.5
O1—C4—C5	122.36 (13)	H12A—C12—H12C	109.5
N2—C4—C5	115.95 (12)	H12B—C12—H12C	109.5
C4—C5—C6	111.57 (12)	C9—C13—H13A	109.5
C4—C5—H5A	109.3	C9—C13—H13B	109.5
C6—C5—H5A	109.3	H13A—C13—H13B	109.5
C4—C5—H5B	109.3	C9—C13—H13C	109.5
C6—C5—H5B	109.3	H13A—C13—H13C	109.5
H5A—C5—H5B	108.0	H13B—C13—H13C	109.5
C7—C6—C11	119.71 (13)	C11—C14—H14A	109.5
C7—C6—C5	120.39 (13)	C11—C14—H14B	109.5
C11—C6—C5	119.87 (13)	H14A—C14—H14B	109.5
C8—C7—C6	118.59 (13)	C11—C14—H14C	109.5
C8—C7—C12	119.60 (13)	H14A—C14—H14C	109.5
C6—C7—C12	121.81 (13)	H14B—C14—H14C	109.5
C9—C8—C7	122.52 (14)

C3—N1—C1—C2	−0.6 (2)	C5—C6—C7—C8	−178.83 (13)
N1—C1—C2—S1	0.76 (19)	C11—C6—C7—C12	178.50 (13)
C3—S1—C2—C1	−0.54 (13)	C5—C6—C7—C12	0.6 (2)
C1—N1—C3—N2	179.97 (13)	C6—C7—C8—C9	0.8 (2)
C1—N1—C3—S1	0.13 (17)	C12—C7—C8—C9	−178.67 (14)
C4—N2—C3—N1	174.78 (13)	C7—C8—C9—C10	−0.2 (2)
C4—N2—C3—S1	−5.40 (19)	C7—C8—C9—C13	179.08 (15)
C2—S1—C3—N1	0.23 (13)	C8—C9—C10—C11	−0.3 (2)
C2—S1—C3—N2	−179.60 (13)	C13—C9—C10—C11	−179.52 (15)
C3—N2—C4—O1	−0.3 (2)	C9—C10—C11—C6	0.1 (2)
C3—N2—C4—C5	−179.76 (13)	C9—C10—C11—C14	179.44 (14)
O1—C4—C5—C6	−49.20 (19)	C7—C6—C11—C10	0.5 (2)
N2—C4—C5—C6	130.23 (13)	C5—C6—C11—C10	178.43 (13)
C4—C5—C6—C7	92.65 (16)	C7—C6—C11—C14	−178.81 (14)
C4—C5—C6—C11	−85.24 (16)	C5—C6—C11—C14	−0.9 (2)
C11—C6—C7—C8	−0.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···N1ⁱ	0.88	2.08	2.9623 (19)	175

Symmetry code: (i) −x+2, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₆N₂OS
M_r	260.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	16.421 (2), 4.6397 (7), 20.1144 (18)
β (°)	123.150 (7)
V (Å³)	1283.1 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.30 × 0.25 × 0.09

Data collection
Diffractometer	Bruker SMART APEXII DUO CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.932, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	13735, 3748, 2999
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.705

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.103, 1.03
No. of reflections	3748
No. of parameters	166
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.51

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···N1ⁱ	0.88	2.08	2.9623 (19)	175

Symmetry code: (i) −x+2, −y+1, −z+2.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5525-2009.

Acknowledgements

The authors thank Universiti Sains Malaysia (USM) for a Research University Grant (No. 1001/PFIZIK/811160). BN also thanks UGC, New Delhi, and the Government of India for the purchase of chemicals through the SAP-DRS-Phase 1 programme.

References

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