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

In the title mol-ecule, C(17)H(14)N(2)OS, the mean plane of the acetamide group forms dihedral angles of 75.79 (5), 81.85 (6) and 12.32 (5)° with the two phenyl rings and the thia-zole ring, respectively. In the crystal, N-H⋯N hydrogen bonds link pairs of mol-ecules into inversion dimers with R(2) (2)(8) ring motifs. The crystal packing is further stabilized by C-H⋯π inter-actions and by π-π inter-actions with a centroid-centroid distance of 3.6977 (5) Å.

Related literature

For the structural similarity of N-substituted 2-aryl­acetamides to the lateral chain of natural benzyl­penicillin, see: Mijin & Marinkovic (2006 ▶); Mijin et al. (2008 ▶). For the coordination abilities of amides, see: Wu et al. (2008 ▶,2010 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Praveen et al. (2011a ▶,b ▶,c ▶); Fun et al. (2011a ▶,b ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C17H14N2OS

M = 294.36

Monoclinic,

a = 5.6915 (1) Å

b = 15.1889 (2) Å

c = 16.5967 (2) Å

β = 97.845 (1)°

V = 1421.32 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 100 K

0.41 × 0.22 × 0.15 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.912, T max = 0.967

23915 measured reflections

6275 independent reflections

5255 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.106

S = 1.05

6275 reflections

194 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.50 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/S1600536812013840/lh5446sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812013840/lh5446Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812013840/lh5446Isup3.cml

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

C17H14N2OS	F(000) = 616
Mr = 294.36	Dx = 1.376 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9903 reflections
a = 5.6915 (1) Å	θ = 2.5–35.1°
b = 15.1889 (2) Å	µ = 0.23 mm−1
c = 16.5967 (2) Å	T = 100 K
β = 97.845 (1)°	Block, colourless
V = 1421.32 (4) Å3	0.41 × 0.22 × 0.15 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	6275 independent reflections
Radiation source: fine-focus sealed tube	5255 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
φ and ω scans	θmax = 35.2°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→9
Tmin = 0.912, Tmax = 0.967	k = −16→24
23915 measured reflections	l = −20→26

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0448P)2 + 0.6018P] where P = (Fo2 + 2Fc2)/3
6275 reflections	(Δ/σ)max = 0.002
194 parameters	Δρmax = 0.50 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 e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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	1.07647 (4)	0.542027 (16)	0.646585 (15)	0.01478 (6)
O1	0.87987 (13)	0.70144 (5)	0.63542 (5)	0.01719 (14)
N1	0.66503 (15)	0.60037 (5)	0.55657 (5)	0.01345 (15)
N2	0.75899 (15)	0.44947 (5)	0.55803 (5)	0.01470 (15)
C1	0.91770 (17)	0.83556 (6)	0.48940 (6)	0.01471 (17)
H1A	0.9756	0.8479	0.5447	0.018*
C2	1.04707 (18)	0.86252 (7)	0.42827 (6)	0.01756 (18)
H2A	1.1911	0.8941	0.4420	0.021*
C3	0.96610 (19)	0.84336 (7)	0.34702 (6)	0.01904 (19)
H3A	1.0555	0.8612	0.3055	0.023*
C4	0.75423 (19)	0.79806 (7)	0.32711 (6)	0.01852 (19)
H4A	0.6989	0.7845	0.2719	0.022*
C5	0.62220 (18)	0.77229 (7)	0.38820 (6)	0.01557 (17)
H5A	0.4761	0.7421	0.3741	0.019*
C6	0.70288 (16)	0.79043 (6)	0.46986 (6)	0.01264 (16)
C7	0.56466 (16)	0.75681 (6)	0.53608 (6)	0.01255 (16)
H7A	0.4160	0.7287	0.5087	0.015*
C8	0.49405 (16)	0.82524 (6)	0.59564 (6)	0.01339 (16)
C9	0.36637 (18)	0.79582 (7)	0.65657 (6)	0.01725 (18)
H9A	0.3371	0.7346	0.6617	0.021*
C10	0.2815 (2)	0.85479 (8)	0.70978 (7)	0.0214 (2)
H10A	0.1937	0.8339	0.7506	0.026*
C11	0.3251 (2)	0.94425 (8)	0.70328 (7)	0.0244 (2)
H11A	0.2682	0.9847	0.7398	0.029*
C12	0.4528 (2)	0.97440 (8)	0.64302 (8)	0.0251 (2)
H12A	0.4833	1.0356	0.6384	0.030*
C13	0.5361 (2)	0.91505 (7)	0.58931 (7)	0.01917 (19)
H13A	0.6222	0.9361	0.5481	0.023*
C14	0.71613 (16)	0.68473 (6)	0.58191 (6)	0.01301 (16)
C15	0.81095 (16)	0.53022 (6)	0.58261 (6)	0.01279 (16)
C16	1.12260 (18)	0.43055 (7)	0.63849 (6)	0.01723 (18)
H16A	1.2576	0.3998	0.6643	0.021*
C17	0.93884 (18)	0.39295 (7)	0.59006 (6)	0.01634 (17)
H17A	0.9337	0.3316	0.5788	0.020*
H1N1	0.548 (3)	0.5890 (11)	0.5207 (10)	0.030 (4)*

	U11	U22	U33	U12	U13	U23
S1	0.01364 (10)	0.01391 (11)	0.01602 (11)	0.00093 (7)	−0.00075 (8)	−0.00122 (8)
O1	0.0178 (3)	0.0141 (3)	0.0181 (3)	0.0002 (2)	−0.0030 (3)	−0.0008 (3)
N1	0.0134 (3)	0.0112 (3)	0.0150 (4)	0.0011 (3)	−0.0009 (3)	−0.0007 (3)
N2	0.0149 (3)	0.0119 (3)	0.0168 (4)	0.0012 (3)	0.0004 (3)	−0.0009 (3)
C1	0.0146 (4)	0.0153 (4)	0.0138 (4)	0.0009 (3)	0.0005 (3)	0.0003 (3)
C2	0.0151 (4)	0.0185 (4)	0.0192 (4)	0.0009 (3)	0.0031 (3)	0.0023 (4)
C3	0.0205 (4)	0.0208 (5)	0.0166 (4)	0.0049 (4)	0.0054 (3)	0.0046 (4)
C4	0.0225 (5)	0.0201 (5)	0.0128 (4)	0.0045 (4)	0.0014 (3)	0.0000 (3)
C5	0.0161 (4)	0.0156 (4)	0.0142 (4)	0.0026 (3)	−0.0007 (3)	−0.0015 (3)
C6	0.0134 (4)	0.0118 (4)	0.0127 (4)	0.0024 (3)	0.0014 (3)	0.0003 (3)
C7	0.0126 (4)	0.0114 (4)	0.0133 (4)	0.0008 (3)	0.0008 (3)	−0.0002 (3)
C8	0.0126 (4)	0.0139 (4)	0.0135 (4)	0.0021 (3)	0.0009 (3)	−0.0009 (3)
C9	0.0156 (4)	0.0192 (4)	0.0172 (4)	0.0015 (3)	0.0032 (3)	0.0018 (3)
C10	0.0201 (5)	0.0283 (5)	0.0166 (4)	0.0051 (4)	0.0057 (4)	0.0008 (4)
C11	0.0271 (5)	0.0261 (5)	0.0207 (5)	0.0083 (4)	0.0061 (4)	−0.0047 (4)
C12	0.0321 (6)	0.0159 (5)	0.0289 (6)	0.0043 (4)	0.0101 (5)	−0.0039 (4)
C13	0.0236 (5)	0.0137 (4)	0.0216 (5)	0.0023 (3)	0.0081 (4)	−0.0003 (4)
C14	0.0142 (4)	0.0119 (4)	0.0131 (4)	0.0000 (3)	0.0024 (3)	0.0000 (3)
C15	0.0126 (4)	0.0133 (4)	0.0125 (4)	0.0003 (3)	0.0019 (3)	0.0002 (3)
C16	0.0167 (4)	0.0152 (4)	0.0192 (4)	0.0036 (3)	0.0003 (3)	−0.0002 (3)
C17	0.0166 (4)	0.0129 (4)	0.0193 (4)	0.0031 (3)	0.0013 (3)	−0.0006 (3)

S1—C16	1.7215 (10)	C6—C7	1.5243 (13)
S1—C15	1.7336 (10)	C7—C8	1.5257 (13)
O1—C14	1.2230 (12)	C7—C14	1.5302 (13)
N1—C14	1.3675 (12)	C7—H7A	1.0000
N1—C15	1.3833 (12)	C8—C13	1.3914 (14)
N1—H1N1	0.847 (17)	C8—C9	1.3967 (14)
N2—C15	1.3135 (12)	C9—C10	1.3899 (15)
N2—C17	1.3853 (13)	C9—H9A	0.9500
C1—C2	1.3939 (14)	C10—C11	1.3881 (17)
C1—C6	1.4006 (13)	C10—H10A	0.9500
C1—H1A	0.9500	C11—C12	1.3914 (18)
C2—C3	1.3950 (15)	C11—H11A	0.9500
C2—H2A	0.9500	C12—C13	1.3954 (15)
C3—C4	1.3885 (16)	C12—H12A	0.9500
C3—H3A	0.9500	C13—H13A	0.9500
C4—C5	1.3978 (15)	C16—C17	1.3552 (14)
C4—H4A	0.9500	C16—H16A	0.9500
C5—C6	1.3977 (13)	C17—H17A	0.9500
C5—H5A	0.9500
C16—S1—C15	88.85 (5)	C13—C8—C7	123.77 (9)
C14—N1—C15	122.15 (8)	C9—C8—C7	117.40 (9)
C14—N1—H1N1	121.4 (11)	C10—C9—C8	120.93 (10)
C15—N1—H1N1	116.2 (11)	C10—C9—H9A	119.5
C15—N2—C17	109.65 (8)	C8—C9—H9A	119.5
C2—C1—C6	120.42 (9)	C11—C10—C9	120.01 (10)
C2—C1—H1A	119.8	C11—C10—H10A	120.0
C6—C1—H1A	119.8	C9—C10—H10A	120.0
C1—C2—C3	120.32 (10)	C10—C11—C12	119.63 (10)
C1—C2—H2A	119.8	C10—C11—H11A	120.2
C3—C2—H2A	119.8	C12—C11—H11A	120.2
C4—C3—C2	119.67 (10)	C11—C12—C13	120.18 (11)
C4—C3—H3A	120.2	C11—C12—H12A	119.9
C2—C3—H3A	120.2	C13—C12—H12A	119.9
C3—C4—C5	120.10 (9)	C8—C13—C12	120.55 (10)
C3—C4—H4A	120.0	C8—C13—H13A	119.7
C5—C4—H4A	120.0	C12—C13—H13A	119.7
C6—C5—C4	120.68 (9)	O1—C14—N1	121.79 (9)
C6—C5—H5A	119.7	O1—C14—C7	122.29 (9)
C4—C5—H5A	119.7	N1—C14—C7	115.83 (8)
C5—C6—C1	118.81 (9)	N2—C15—N1	121.47 (9)
C5—C6—C7	119.96 (9)	N2—C15—S1	115.30 (7)
C1—C6—C7	121.14 (8)	N1—C15—S1	123.21 (7)
C6—C7—C8	116.51 (8)	C17—C16—S1	110.32 (7)
C6—C7—C14	106.68 (7)	C17—C16—H16A	124.8
C8—C7—C14	110.22 (8)	S1—C16—H16A	124.8
C6—C7—H7A	107.7	C16—C17—N2	115.87 (9)
C8—C7—H7A	107.7	C16—C17—H17A	122.1
C14—C7—H7A	107.7	N2—C17—H17A	122.1
C13—C8—C9	118.70 (9)
C6—C1—C2—C3	−1.20 (15)	C10—C11—C12—C13	0.13 (19)
C1—C2—C3—C4	0.70 (16)	C9—C8—C13—C12	0.21 (16)
C2—C3—C4—C5	0.39 (16)	C7—C8—C13—C12	175.82 (10)
C3—C4—C5—C6	−1.01 (15)	C11—C12—C13—C8	−0.42 (18)
C4—C5—C6—C1	0.51 (14)	C15—N1—C14—O1	−7.86 (15)
C4—C5—C6—C7	−176.13 (9)	C15—N1—C14—C7	168.96 (8)
C2—C1—C6—C5	0.59 (14)	C6—C7—C14—O1	81.74 (11)
C2—C1—C6—C7	177.19 (9)	C8—C7—C14—O1	−45.64 (12)
C5—C6—C7—C8	−126.30 (9)	C6—C7—C14—N1	−95.07 (9)
C1—C6—C7—C8	57.14 (12)	C8—C7—C14—N1	137.56 (9)
C5—C6—C7—C14	110.15 (9)	C17—N2—C15—N1	177.26 (9)
C1—C6—C7—C14	−66.41 (11)	C17—N2—C15—S1	−0.88 (11)
C6—C7—C8—C13	4.06 (13)	C14—N1—C15—N2	179.68 (9)
C14—C7—C8—C13	125.77 (10)	C14—N1—C15—S1	−2.33 (13)
C6—C7—C8—C9	179.72 (8)	C16—S1—C15—N2	0.84 (8)
C14—C7—C8—C9	−58.57 (11)	C16—S1—C15—N1	−177.26 (9)
C13—C8—C9—C10	0.29 (15)	C15—S1—C16—C17	−0.54 (8)
C7—C8—C9—C10	−175.60 (9)	S1—C16—C17—N2	0.17 (12)
C8—C9—C10—C11	−0.59 (16)	C15—N2—C17—C16	0.44 (13)
C9—C10—C11—C12	0.37 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···N2i	0.848 (17)	2.116 (17)	2.9600 (12)	173.0 (17)
C1—H1A···Cg2ii	0.95	2.88	3.6647 (11)	141
C12—H12A···Cg1iii	0.95	2.92	3.6143 (13)	131
C17—H17A···Cg1iv	0.95	2.61	3.4381 (11)	146

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯N2i	0.848 (17)	2.116 (17)	2.9600 (12)	173.0 (17)
C1—H1A⋯Cg2ii	0.95	2.88	3.6647 (11)	141
C12—H12A⋯Cg1iii	0.95	2.92	3.6143 (13)	131
C17—H17A⋯Cg1iv	0.95	2.61	3.4381 (11)	146

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .