2-(4-Chloro­phen­yl)-N-(1,3-thia­zol-2-yl)acetamide

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

doi:10.1107/S1600536812034629

organic compounds

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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page o2679

doi:10.1107/S1600536812034629

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2-(4-Chlorophenyl)-N-(1,3-thiazol-2-yl)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 31 July 2012; accepted 3 August 2012; online 11 August 2012)

In the title compound, C₁₁H₉ClN₂OS, the thiazole ring is nearly planar (r.m.s. deviation = 0.003 Å) and forms a dihedral angle of 64.18 (7)° with the bezene ring. In the crystal, inversion dimers linked by pairs of N—H⋯N_t (t = thiazole) hydrogen bonds generate R₂²(8) loops.

Related literature

For general background to the title compound and for related structures, see: Fun et al. (2011a ,b , 2012a ,b ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₁H₉ClN₂OS
M_r = 252.71
Monoclinic, P 2₁ /c
a = 13.9169 (13) Å
b = 5.5188 (5) Å
c = 15.1836 (14) Å
β = 100.311 (2)°
V = 1147.34 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.49 mm⁻¹
T = 296 K
0.35 × 0.29 × 0.18 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.847, T_max = 0.918
11463 measured reflections
3421 independent reflections
2769 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.116
S = 1.02
3421 reflections
149 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯N1ⁱ	0.866 (18)	2.096 (18)	2.9606 (16)	176.2 (17)
Symmetry code: (i) -x+1, -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: 10.1107/S1600536812034629/hb6927sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812034629/hb6927Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812034629/hb6927Isup3.cml

checkCIF report

Comment top

In continuation of our work on synthesis of amides (Fun et al., 2011a, 2011b, 2012a, 2012b), 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 nearly planar (r.m.s. deviation = 0.003 Å) and it forms a dihedral angle of 64.18 (7)° with the bezene ring (C6-C11). Bond lengths and angles are within normal ranges and are comparable to related structures (Fun et al., 2011a, 2011b, 2012a, 2012b).

In the crystal structure, Fig. 2, molecules are linked into an inversion dimer by pairs of N2–H1N2···N1 hydrogen bonds (Table 1), generating R₂²(8) ring motifs (Bernstein et al., 1995).

Related literature top

For general background to the title compound and for related structures, see: Fun et al. (2011a,b, 2012a,b). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

4-Chlorophenylacetic acid (0.170 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. The resulting solution 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). Orange blocks were grown from an acetone and toluene (1:1) solvent mixture by the slow evaporation method (m.p.: 441K).

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 30% 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.

2-(4-Chlorophenyl)-N-(1,3-thiazol-2-yl)acetamide top

Crystal data top

C₁₁H₉ClN₂OS	F(000) = 520
M_r = 252.71	D_x = 1.463 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4547 reflections
a = 13.9169 (13) Å	θ = 2.7–30.3°
b = 5.5188 (5) Å	µ = 0.49 mm⁻¹
c = 15.1836 (14) Å	T = 296 K
β = 100.311 (2)°	Block, orange
V = 1147.34 (18) Å³	0.35 × 0.29 × 0.18 mm
Z = 4

Data collection top

Bruker SMART APEXII DUO CCD diffractometer	3421 independent reflections
Radiation source: fine-focus sealed tube	2769 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ϕ and ω scans	θ_max = 30.3°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −19→19
T_min = 0.847, T_max = 0.918	k = −7→7
11463 measured reflections	l = −21→21

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0629P)² + 0.2113P] where P = (F_o² + 2F_c²)/3
3421 reflections	(Δ/σ)_max = 0.001
149 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₁H₉ClN₂OS	V = 1147.34 (18) Å³
M_r = 252.71	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.9169 (13) Å	µ = 0.49 mm⁻¹
b = 5.5188 (5) Å	T = 296 K
c = 15.1836 (14) Å	0.35 × 0.29 × 0.18 mm
β = 100.311 (2)°

Data collection top

Bruker SMART APEXII DUO CCD diffractometer	3421 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2769 reflections with I > 2σ(I)
T_min = 0.847, T_max = 0.918	R_int = 0.020
11463 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.29 e Å⁻³
3421 reflections	Δρ_min = −0.29 e Å⁻³
149 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.

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
Cl1	−0.20822 (3)	0.54220 (12)	0.82496 (4)	0.08193 (19)
S1	0.39710 (3)	1.03306 (7)	1.11917 (3)	0.04855 (13)
O1	0.23806 (7)	0.8565 (2)	1.00294 (8)	0.0547 (3)
N1	0.53067 (8)	0.7454 (2)	1.08411 (8)	0.0444 (3)
N2	0.37558 (8)	0.6335 (2)	1.00962 (8)	0.0410 (2)
C1	0.51611 (12)	1.0855 (3)	1.16882 (11)	0.0530 (4)
H1A	0.5365	1.2115	1.2085	0.064*
C2	0.57568 (11)	0.9199 (3)	1.14263 (11)	0.0503 (3)
H2A	0.6429	0.9223	1.1626	0.060*
C3	0.43688 (9)	0.7846 (2)	1.06618 (8)	0.0370 (3)
C4	0.27847 (9)	0.6768 (2)	0.98005 (9)	0.0409 (3)
C5	0.22953 (11)	0.4817 (3)	0.91743 (12)	0.0508 (4)
H5A	0.2547	0.4902	0.8619	0.061*
H5B	0.2473	0.3248	0.9442	0.061*
C6	0.11993 (10)	0.4988 (2)	0.89603 (9)	0.0396 (3)
C7	0.06207 (10)	0.3160 (2)	0.92138 (9)	0.0425 (3)
H7A	0.0916	0.1835	0.9531	0.051*
C8	−0.03890 (11)	0.3270 (3)	0.90033 (10)	0.0458 (3)
H8A	−0.0773	0.2037	0.9174	0.055*
C9	−0.08118 (10)	0.5259 (3)	0.85331 (9)	0.0457 (3)
C10	−0.02621 (11)	0.7100 (3)	0.82739 (9)	0.0501 (3)
H10A	−0.0562	0.8422	0.7958	0.060*
C11	0.07454 (11)	0.6961 (3)	0.84901 (9)	0.0465 (3)
H11A	0.1124	0.8204	0.8319	0.056*
H1N2	0.4009 (14)	0.518 (3)	0.9827 (12)	0.052 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0398 (2)	0.1231 (5)	0.0797 (3)	0.0207 (2)	0.0020 (2)	0.0027 (3)
S1	0.0515 (2)	0.03917 (19)	0.0564 (2)	0.00832 (14)	0.01343 (16)	−0.00790 (14)
O1	0.0402 (5)	0.0473 (6)	0.0736 (7)	0.0117 (4)	0.0022 (5)	−0.0138 (5)
N1	0.0366 (5)	0.0441 (6)	0.0521 (6)	0.0018 (5)	0.0068 (5)	−0.0104 (5)
N2	0.0334 (5)	0.0361 (5)	0.0530 (6)	0.0044 (4)	0.0067 (5)	−0.0074 (5)
C1	0.0612 (9)	0.0455 (8)	0.0523 (8)	−0.0065 (7)	0.0099 (7)	−0.0129 (6)
C2	0.0433 (7)	0.0531 (8)	0.0529 (8)	−0.0051 (6)	0.0044 (6)	−0.0103 (6)
C3	0.0374 (6)	0.0328 (6)	0.0418 (6)	0.0036 (5)	0.0098 (5)	−0.0006 (5)
C4	0.0347 (6)	0.0398 (6)	0.0480 (7)	0.0047 (5)	0.0069 (5)	−0.0009 (5)
C5	0.0387 (7)	0.0504 (8)	0.0615 (9)	0.0064 (6)	0.0041 (6)	−0.0147 (7)
C6	0.0377 (6)	0.0405 (6)	0.0388 (6)	0.0062 (5)	0.0016 (5)	−0.0073 (5)
C7	0.0460 (7)	0.0368 (6)	0.0422 (6)	0.0087 (5)	0.0012 (5)	−0.0007 (5)
C8	0.0445 (7)	0.0466 (7)	0.0465 (7)	0.0006 (6)	0.0085 (6)	−0.0025 (6)
C9	0.0369 (6)	0.0582 (8)	0.0395 (6)	0.0115 (6)	0.0003 (5)	−0.0069 (6)
C10	0.0560 (8)	0.0472 (8)	0.0421 (7)	0.0150 (6)	−0.0051 (6)	0.0032 (6)
C11	0.0524 (8)	0.0415 (7)	0.0437 (7)	−0.0003 (6)	0.0033 (6)	0.0019 (5)

Geometric parameters (Å, º) top

Cl1—C9	1.7455 (15)	C5—C6	1.5045 (19)
S1—C1	1.7170 (17)	C5—H5A	0.9700
S1—C3	1.7300 (13)	C5—H5B	0.9700
O1—C4	1.2211 (16)	C6—C7	1.388 (2)
N1—C3	1.3029 (17)	C6—C11	1.3904 (19)
N1—C2	1.3820 (18)	C7—C8	1.386 (2)
N2—C4	1.3666 (16)	C7—H7A	0.9300
N2—C3	1.3778 (17)	C8—C9	1.382 (2)
N2—H1N2	0.868 (19)	C8—H8A	0.9300
C1—C2	1.341 (2)	C9—C10	1.371 (2)
C1—H1A	0.9300	C10—C11	1.384 (2)
C2—H2A	0.9300	C10—H10A	0.9300
C4—C5	1.515 (2)	C11—H11A	0.9300

C1—S1—C3	88.50 (7)	C4—C5—H5B	108.6
C3—N1—C2	109.91 (12)	H5A—C5—H5B	107.6
C4—N2—C3	124.38 (11)	C7—C6—C11	118.63 (13)
C4—N2—H1N2	115.8 (12)	C7—C6—C5	120.71 (13)
C3—N2—H1N2	118.8 (12)	C11—C6—C5	120.65 (14)
C2—C1—S1	110.73 (12)	C8—C7—C6	121.25 (13)
C2—C1—H1A	124.6	C8—C7—H7A	119.4
S1—C1—H1A	124.6	C6—C7—H7A	119.4
C1—C2—N1	115.61 (14)	C9—C8—C7	118.34 (14)
C1—C2—H2A	122.2	C9—C8—H8A	120.8
N1—C2—H2A	122.2	C7—C8—H8A	120.8
N1—C3—N2	121.01 (11)	C10—C9—C8	121.92 (13)
N1—C3—S1	115.24 (10)	C10—C9—Cl1	118.92 (11)
N2—C3—S1	123.75 (10)	C8—C9—Cl1	119.15 (13)
O1—C4—N2	121.81 (13)	C9—C10—C11	118.98 (13)
O1—C4—C5	125.28 (12)	C9—C10—H10A	120.5
N2—C4—C5	112.91 (11)	C11—C10—H10A	120.5
C6—C5—C4	114.56 (11)	C10—C11—C6	120.88 (14)
C6—C5—H5A	108.6	C10—C11—H11A	119.6
C4—C5—H5A	108.6	C6—C11—H11A	119.6
C6—C5—H5B	108.6

C3—S1—C1—C2	0.48 (13)	C4—C5—C6—C7	−116.45 (15)
S1—C1—C2—N1	−0.8 (2)	C4—C5—C6—C11	64.72 (19)
C3—N1—C2—C1	0.7 (2)	C11—C6—C7—C8	0.3 (2)
C2—N1—C3—N2	−179.52 (13)	C5—C6—C7—C8	−178.55 (13)
C2—N1—C3—S1	−0.32 (16)	C6—C7—C8—C9	−0.1 (2)
C4—N2—C3—N1	−172.65 (13)	C7—C8—C9—C10	0.0 (2)
C4—N2—C3—S1	8.23 (19)	C7—C8—C9—Cl1	179.30 (11)
C1—S1—C3—N1	−0.08 (12)	C8—C9—C10—C11	0.0 (2)
C1—S1—C3—N2	179.09 (12)	Cl1—C9—C10—C11	−179.33 (11)
C3—N2—C4—O1	−0.6 (2)	C9—C10—C11—C6	0.2 (2)
C3—N2—C4—C5	179.13 (13)	C7—C6—C11—C10	−0.3 (2)
O1—C4—C5—C6	−10.4 (2)	C5—C6—C11—C10	178.52 (13)
N2—C4—C5—C6	169.89 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···N1ⁱ	0.866 (18)	2.096 (18)	2.9606 (16)	176.2 (17)

Symmetry code: (i) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₁H₉ClN₂OS
M_r	252.71
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	13.9169 (13), 5.5188 (5), 15.1836 (14)
β (°)	100.311 (2)
V (Å³)	1147.34 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.49
Crystal size (mm)	0.35 × 0.29 × 0.18

Data collection
Diffractometer	Bruker SMART APEXII DUO CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.847, 0.918
No. of measured, independent and observed [I > 2σ(I)] reflections	11463, 3421, 2769
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.710

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.116, 1.02
No. of reflections	3421
No. of parameters	149
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.29

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—H1N2···N1ⁱ	0.866 (18)	2.096 (18)	2.9606 (16)	176.2 (17)

Symmetry code: (i) −x+1, −y+1, −z+2.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5525-2009.

Acknowledgements

The authors would like to thank Universiti Sains Malaysia (USM) for the Research University Grant (No. 1001/PFIZIK/811160). BN also thanks the 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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