2-(Naphthalen-1-yl)-N-(1,3-thia-zol-2-yl)acetamide.

In the title compound, C(15)H(12)N(2)OS, the naphthalene ring system [maximum deviation = 0.026 (1) Å] forms a dihedral angle of 85.69 (6)° with the thia-zole ring [maximum deviation = 0.010 (1) Å]. In the crystal, inversion dimers linked by pairs of N-H⋯N hydrogen bonds generate R(2) (2)(8) loops. The dimers are linked by C-H⋯O hydrogen bonds into chains propagating along [110].

Related literature

For general background to and the related structures of the title compound, see: Fun et al. (2010 ▶, 2011a ▶,b ▶, 2012 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C15H12N2OS

M = 268.33

Monoclinic,

a = 5.2668 (1) Å

b = 13.0861 (2) Å

c = 18.5373 (3) Å

β = 105.640 (1)°

V = 1230.32 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 100 K

0.39 × 0.22 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.907, T max = 0.956

17425 measured reflections

4470 independent reflections

3657 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.108

S = 1.06

4470 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.28 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812031583/hb6894sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812031583/hb6894Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812031583/hb6894Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H12N2OS	F(000) = 560
Mr = 268.33	Dx = 1.449 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5904 reflections
a = 5.2668 (1) Å	θ = 2.3–32.5°
b = 13.0861 (2) Å	µ = 0.26 mm−1
c = 18.5373 (3) Å	T = 100 K
β = 105.640 (1)°	Block, brown
V = 1230.32 (4) Å3	0.39 × 0.22 × 0.18 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	4470 independent reflections
Radiation source: fine-focus sealed tube	3657 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
φ and ω scans	θmax = 32.6°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −7→7
Tmin = 0.907, Tmax = 0.956	k = −19→19
17425 measured reflections	l = −26→28

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0389P)2 + 0.749P] where P = (Fo2 + 2Fc2)/3
4470 reflections	(Δ/σ)max = 0.001
172 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

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.

	x	y	z	Uiso*/Ueq
S1	0.40765 (6)	0.66213 (3)	−0.105525 (19)	0.01874 (9)
O1	0.7884 (2)	0.80307 (8)	−0.04709 (6)	0.0259 (2)
N1	0.6697 (2)	0.49519 (9)	−0.06570 (6)	0.0169 (2)
N2	0.9062 (2)	0.64044 (8)	−0.01161 (6)	0.0163 (2)
H1	1.0220	0.6004	0.0140	0.020*
C1	0.2553 (3)	0.54707 (11)	−0.13559 (8)	0.0199 (3)
H1A	0.0793	0.5399	−0.1659	0.024*
C2	0.4222 (3)	0.46858 (11)	−0.10991 (8)	0.0189 (3)
H2A	0.3726	0.3994	−0.1215	0.023*
C3	0.6867 (2)	0.59466 (10)	−0.05809 (7)	0.0154 (2)
C4	0.9383 (3)	0.74460 (10)	−0.00491 (8)	0.0178 (2)
C5	1.1574 (3)	0.77925 (11)	0.06208 (8)	0.0190 (3)
H5A	1.2188	0.8483	0.0529	0.023*
H5B	1.3087	0.7316	0.0705	0.023*
C6	1.0495 (2)	0.78093 (10)	0.13046 (8)	0.0174 (2)
C7	1.1084 (3)	0.70263 (11)	0.18172 (8)	0.0191 (3)
H7A	1.2283	0.6509	0.1761	0.023*
C8	0.9946 (3)	0.69737 (11)	0.24260 (8)	0.0211 (3)
H8A	1.0395	0.6428	0.2775	0.025*
C9	0.8202 (3)	0.77057 (11)	0.25133 (8)	0.0210 (3)
H9A	0.7405	0.7655	0.2915	0.025*
C10	0.7573 (2)	0.85443 (10)	0.20059 (8)	0.0178 (2)
C11	0.5793 (3)	0.93187 (11)	0.20968 (8)	0.0220 (3)
H11A	0.5005	0.9276	0.2500	0.026*
C12	0.5200 (3)	1.01268 (11)	0.16105 (8)	0.0226 (3)
H12A	0.3992	1.0636	0.1674	0.027*
C13	0.6382 (3)	1.02017 (11)	0.10154 (8)	0.0218 (3)
H13A	0.5987	1.0769	0.0684	0.026*
C14	0.8101 (3)	0.94631 (10)	0.09084 (8)	0.0199 (3)
H14A	0.8875	0.9525	0.0503	0.024*
C15	0.8737 (2)	0.86059 (10)	0.13969 (7)	0.0168 (2)

	U11	U22	U33	U12	U13	U23
S1	0.01559 (14)	0.01887 (16)	0.02027 (16)	0.00490 (11)	0.00230 (11)	0.00192 (12)
O1	0.0310 (6)	0.0161 (5)	0.0268 (5)	0.0046 (4)	0.0013 (4)	0.0015 (4)
N1	0.0141 (5)	0.0160 (5)	0.0192 (5)	0.0005 (4)	0.0021 (4)	−0.0008 (4)
N2	0.0140 (5)	0.0131 (5)	0.0203 (5)	0.0017 (4)	0.0018 (4)	0.0008 (4)
C1	0.0138 (5)	0.0244 (7)	0.0196 (6)	0.0000 (5)	0.0013 (4)	−0.0008 (5)
C2	0.0146 (5)	0.0209 (6)	0.0197 (6)	−0.0015 (5)	0.0020 (4)	−0.0016 (5)
C3	0.0132 (5)	0.0161 (6)	0.0165 (5)	0.0016 (4)	0.0034 (4)	0.0007 (4)
C4	0.0180 (6)	0.0151 (6)	0.0214 (6)	0.0007 (4)	0.0073 (5)	−0.0011 (5)
C5	0.0170 (6)	0.0163 (6)	0.0240 (7)	−0.0008 (4)	0.0063 (5)	−0.0028 (5)
C6	0.0142 (5)	0.0159 (6)	0.0210 (6)	−0.0018 (4)	0.0027 (4)	−0.0031 (5)
C7	0.0168 (6)	0.0158 (6)	0.0223 (6)	−0.0002 (4)	0.0013 (5)	−0.0019 (5)
C8	0.0213 (6)	0.0187 (6)	0.0201 (6)	−0.0015 (5)	0.0002 (5)	0.0016 (5)
C9	0.0221 (6)	0.0214 (7)	0.0185 (6)	−0.0030 (5)	0.0037 (5)	−0.0016 (5)
C10	0.0147 (5)	0.0176 (6)	0.0194 (6)	−0.0028 (4)	0.0014 (4)	−0.0049 (5)
C11	0.0210 (6)	0.0214 (7)	0.0238 (7)	−0.0010 (5)	0.0063 (5)	−0.0063 (5)
C12	0.0209 (6)	0.0178 (6)	0.0274 (7)	0.0017 (5)	0.0035 (5)	−0.0057 (5)
C13	0.0236 (6)	0.0137 (6)	0.0254 (7)	0.0016 (5)	0.0021 (5)	−0.0019 (5)
C14	0.0210 (6)	0.0162 (6)	0.0221 (6)	−0.0012 (5)	0.0052 (5)	−0.0018 (5)
C15	0.0145 (5)	0.0155 (6)	0.0189 (6)	−0.0018 (4)	0.0019 (4)	−0.0029 (4)

S1—C1	1.7264 (15)	C7—C8	1.415 (2)
S1—C3	1.7367 (13)	C7—H7A	0.9500
O1—C4	1.2197 (17)	C8—C9	1.367 (2)
N1—C3	1.3098 (17)	C8—H8A	0.9500
N1—C2	1.3846 (17)	C9—C10	1.425 (2)
N2—C4	1.3749 (17)	C9—H9A	0.9500
N2—C3	1.3786 (16)	C10—C11	1.4209 (19)
N2—H1	0.8458	C10—C15	1.4247 (19)
C1—C2	1.3523 (19)	C11—C12	1.370 (2)
C1—H1A	0.9500	C11—H11A	0.9500
C2—H2A	0.9500	C12—C13	1.409 (2)
C4—C5	1.5188 (19)	C12—H12A	0.9500
C5—C6	1.5229 (19)	C13—C14	1.375 (2)
C5—H5A	0.9900	C13—H13A	0.9500
C5—H5B	0.9900	C14—C15	1.4238 (19)
C6—C7	1.3747 (19)	C14—H14A	0.9500
C6—C15	1.4350 (18)
C1—S1—C3	88.65 (6)	C6—C7—H7A	119.3
C3—N1—C2	109.86 (11)	C8—C7—H7A	119.3
C4—N2—C3	123.32 (11)	C9—C8—C7	120.21 (13)
C4—N2—H1	120.7	C9—C8—H8A	119.9
C3—N2—H1	116.0	C7—C8—H8A	119.9
C2—C1—S1	110.32 (10)	C8—C9—C10	120.38 (13)
C2—C1—H1A	124.8	C8—C9—H9A	119.8
S1—C1—H1A	124.8	C10—C9—H9A	119.8
C1—C2—N1	115.87 (13)	C11—C10—C15	119.47 (13)
C1—C2—H2A	122.1	C11—C10—C9	120.96 (13)
N1—C2—H2A	122.1	C15—C10—C9	119.57 (12)
N1—C3—N2	121.37 (11)	C12—C11—C10	120.89 (14)
N1—C3—S1	115.27 (10)	C12—C11—H11A	119.6
N2—C3—S1	123.24 (10)	C10—C11—H11A	119.6
O1—C4—N2	121.42 (13)	C11—C12—C13	119.88 (13)
O1—C4—C5	123.70 (13)	C11—C12—H12A	120.1
N2—C4—C5	114.69 (12)	C13—C12—H12A	120.1
C4—C5—C6	108.24 (11)	C14—C13—C12	120.76 (14)
C4—C5—H5A	110.1	C14—C13—H13A	119.6
C6—C5—H5A	110.1	C12—C13—H13A	119.6
C4—C5—H5B	110.1	C13—C14—C15	120.87 (13)
C6—C5—H5B	110.1	C13—C14—H14A	119.6
H5A—C5—H5B	108.4	C15—C14—H14A	119.6
C7—C6—C15	119.46 (13)	C14—C15—C10	118.10 (12)
C7—C6—C5	119.95 (12)	C14—C15—C6	123.03 (13)
C15—C6—C5	120.50 (12)	C10—C15—C6	118.87 (12)
C6—C7—C8	121.48 (13)
C3—S1—C1—C2	−1.29 (11)	C7—C8—C9—C10	−1.9 (2)
S1—C1—C2—N1	0.83 (16)	C8—C9—C10—C11	−179.05 (13)
C3—N1—C2—C1	0.34 (18)	C8—C9—C10—C15	1.2 (2)
C2—N1—C3—N2	174.69 (12)	C15—C10—C11—C12	−0.5 (2)
C2—N1—C3—S1	−1.39 (15)	C9—C10—C11—C12	179.70 (13)
C4—N2—C3—N1	176.49 (13)	C10—C11—C12—C13	−0.7 (2)
C4—N2—C3—S1	−7.74 (18)	C11—C12—C13—C14	1.0 (2)
C1—S1—C3—N1	1.59 (11)	C12—C13—C14—C15	−0.2 (2)
C1—S1—C3—N2	−174.41 (12)	C13—C14—C15—C10	−1.0 (2)
C3—N2—C4—O1	−9.5 (2)	C13—C14—C15—C6	179.30 (13)
C3—N2—C4—C5	165.66 (12)	C11—C10—C15—C14	1.30 (18)
O1—C4—C5—C6	92.07 (16)	C9—C10—C15—C14	−178.91 (12)
N2—C4—C5—C6	−82.97 (14)	C11—C10—C15—C6	−178.95 (12)
C4—C5—C6—C7	101.68 (14)	C9—C10—C15—C6	0.84 (18)
C4—C5—C6—C15	−74.62 (15)	C7—C6—C15—C14	177.58 (12)
C15—C6—C7—C8	1.5 (2)	C5—C6—C15—C14	−6.11 (19)
C5—C6—C7—C8	−174.79 (12)	C7—C6—C15—C10	−2.16 (18)
C6—C7—C8—C9	0.5 (2)	C5—C6—C15—C10	174.15 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···N1i	0.85	2.07	2.9099 (16)	172
C13—H13A···O1ii	0.95	2.52	3.1929 (19)	128

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1⋯N1i	0.85	2.07	2.9099 (16)	172
C13—H13A⋯O1ii	0.95	2.52	3.1929 (19)	128

Symmetry codes: (i) ; (ii) .