4-Methyl-N-[2-(pyridin-2-yl)ethyl-carbamo-thio-yl]benzamide.

In the title compound, C16H17N3OS, the dihedral angle between the planes of the benzene and pyridine rings is 71.33 (15)°. An intra-molecular N-H⋯O hydrogen bond is present. In the crystal, weak aromatic C-H⋯O hydrogen bonds link the mol-ecules into chains extending along a.

Related literature

For related structures, see: Saeed & Flörke (2007 ▶); Yusof et al. (2008 ▶, 2011 ▶); Shoukat et al. (2007 ▶); Hassan et al. (2008a ▶,b ▶,c ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For graph-set analysis, see Bernstein et al. (1995 ▶).

Experimental

Crystal data

C16H17N3OS

M = 299.39

Monoclinic,

a = 16.0467 (12) Å

b = 4.8824 (4) Å

c = 23.0403 (18) Å

β = 124.997 (5)°

V = 1478.7 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 100 K

0.47 × 0.20 × 0.14 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.903, T max = 0.980

12777 measured reflections

3409 independent reflections

2221 reflections with I > 2σ(I)

R int = 0.082

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.182

S = 1.04

3409 reflections

199 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.66 e Å−3

Δρmin = −0.44 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAIn class="Chemical">NT; 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) I. DOI: 10.1107/S1600536814016377/zs2306sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814016377/zs2306Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814016377/zs2306Isup3.cml

CCDC reference: 1014035

Additional supporting information: crystallographic information; 3D view; checkCIF report

C16H17N3OS	F(000) = 632
Mr = 299.39	Dx = 1.345 Mg m−3
Monoclinic, P21/c	Melting point: 399.3 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 16.0467 (12) Å	θ = 2.6–25.5°
b = 4.8824 (4) Å	µ = 0.22 mm−1
c = 23.0403 (18) Å	T = 100 K
β = 124.997 (5)°	Block, colourless
V = 1478.7 (2) Å3	0.47 × 0.20 × 0.14 mm
Z = 4

Bruker APEXII CCD diffractometer	3409 independent reflections
Radiation source: fine-focus sealed tube	2221 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.082
φ and ω scans	θmax = 27.6°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −17→20
Tmin = 0.903, Tmax = 0.980	k = −6→6
12777 measured reflections	l = −30→24

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.182	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0899P)2] where P = (Fo2 + 2Fc2)/3
3409 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.66 e Å−3
0 restraints	Δρmin = −0.44 e Å−3

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	0.72652 (6)	0.04528 (17)	0.87044 (4)	0.0286 (3)
O2	0.78657 (14)	0.5226 (4)	0.72802 (11)	0.0272 (5)
N1	0.69712 (19)	0.3898 (5)	0.77218 (13)	0.0227 (6)
N2	0.84392 (17)	0.1337 (5)	0.82384 (13)	0.0211 (5)
N3	1.02858 (17)	0.3126 (5)	0.84401 (12)	0.0229 (6)
C1	0.6442 (2)	0.9043 (6)	0.63777 (15)	0.0236 (7)
H1A	0.7034	0.8759	0.6386	0.028*
C2	0.5737 (2)	1.0965 (6)	0.59246 (15)	0.0250 (7)
H2A	0.5853	1.1996	0.5627	0.030*
C3	0.4852 (2)	1.1422 (6)	0.58956 (15)	0.0227 (6)
C4	0.4718 (2)	0.9901 (6)	0.63468 (16)	0.0246 (7)
H4A	0.4128	1.0199	0.6341	0.030*
C5	0.5426 (2)	0.7954 (6)	0.68073 (15)	0.0245 (7)
H5A	0.5315	0.6933	0.7108	0.029*
C6	0.6301 (2)	0.7508 (6)	0.68249 (14)	0.0200 (6)
C7	0.7113 (2)	0.5479 (6)	0.72911 (14)	0.0203 (6)
C8	0.7611 (2)	0.1903 (6)	0.82127 (15)	0.0218 (6)
C9	0.9261 (2)	−0.0462 (6)	0.87572 (15)	0.0240 (7)
H9A	0.9508	−0.1556	0.8523	0.029*
H9B	0.9001	−0.1743	0.8952	0.029*
C10	1.0135 (2)	0.1207 (6)	0.93572 (15)	0.0242 (7)
H10A	0.9874	0.2330	0.9578	0.029*
H10B	1.0650	−0.0066	0.9723	0.029*
C11	1.0649 (2)	0.3085 (6)	0.91261 (15)	0.0224 (6)
C12	1.1454 (2)	0.4739 (6)	0.96253 (16)	0.0282 (7)
H12A	1.1707	0.4633	1.0112	0.034*
C13	1.1880 (2)	0.6550 (7)	0.93981 (18)	0.0315 (8)
H13A	1.2426	0.7710	0.9728	0.038*
C14	1.1503 (2)	0.6643 (6)	0.86918 (18)	0.0323 (8)
H14A	1.1775	0.7882	0.8523	0.039*
C15	1.0716 (2)	0.4885 (6)	0.82314 (17)	0.0269 (7)
H15A	1.0466	0.4919	0.7745	0.032*
C16	0.4073 (2)	1.3480 (6)	0.53901 (16)	0.0279 (7)
H16C	0.3579	1.3783	0.5505	0.042*
H16D	0.3721	1.2787	0.4904	0.042*
H16A	0.4412	1.5211	0.5431	0.042*
H1N2	0.852 (2)	0.242 (7)	0.7974 (17)	0.039 (10)*
H1N1	0.651 (3)	0.424 (9)	0.775 (2)	0.078 (15)*

	U11	U22	U33	U12	U13	U23
S1	0.0251 (4)	0.0384 (5)	0.0310 (5)	0.0068 (3)	0.0211 (4)	0.0085 (3)
O2	0.0175 (11)	0.0343 (12)	0.0359 (12)	0.0052 (9)	0.0189 (10)	0.0070 (9)
N1	0.0166 (13)	0.0302 (14)	0.0268 (14)	0.0042 (10)	0.0157 (12)	0.0023 (10)
N2	0.0151 (12)	0.0249 (14)	0.0253 (14)	0.0030 (10)	0.0127 (11)	0.0040 (10)
N3	0.0185 (13)	0.0269 (14)	0.0266 (14)	0.0036 (10)	0.0149 (11)	0.0030 (10)
C1	0.0173 (14)	0.0322 (17)	0.0246 (16)	−0.0003 (12)	0.0140 (13)	0.0001 (12)
C2	0.0212 (15)	0.0317 (17)	0.0258 (16)	0.0013 (12)	0.0156 (13)	0.0055 (13)
C3	0.0184 (15)	0.0252 (16)	0.0234 (16)	0.0012 (12)	0.0114 (13)	−0.0001 (12)
C4	0.0180 (15)	0.0286 (16)	0.0311 (17)	0.0010 (12)	0.0163 (13)	0.0005 (13)
C5	0.0235 (16)	0.0284 (17)	0.0273 (16)	0.0017 (12)	0.0180 (14)	0.0038 (13)
C6	0.0154 (14)	0.0229 (15)	0.0214 (15)	−0.0028 (11)	0.0104 (12)	−0.0031 (11)
C7	0.0165 (14)	0.0234 (15)	0.0212 (15)	−0.0030 (11)	0.0109 (12)	−0.0029 (12)
C8	0.0173 (14)	0.0265 (16)	0.0222 (15)	0.0005 (12)	0.0116 (12)	0.0002 (12)
C9	0.0208 (15)	0.0247 (16)	0.0303 (17)	0.0046 (12)	0.0169 (14)	0.0056 (12)
C10	0.0180 (15)	0.0315 (17)	0.0238 (16)	0.0037 (12)	0.0124 (13)	0.0037 (12)
C11	0.0156 (15)	0.0248 (16)	0.0285 (16)	0.0051 (12)	0.0137 (13)	0.0030 (12)
C12	0.0216 (16)	0.0360 (18)	0.0268 (17)	−0.0014 (13)	0.0137 (14)	−0.0002 (13)
C13	0.0214 (16)	0.0293 (17)	0.044 (2)	−0.0020 (13)	0.0185 (15)	−0.0035 (14)
C14	0.0265 (17)	0.0298 (18)	0.052 (2)	0.0030 (14)	0.0292 (17)	0.0059 (15)
C15	0.0246 (16)	0.0330 (18)	0.0327 (17)	0.0063 (13)	0.0220 (14)	0.0052 (13)
C16	0.0229 (16)	0.0327 (18)	0.0286 (17)	0.0048 (13)	0.0150 (14)	0.0027 (13)

S1—C8	1.678 (3)	C5—H5A	0.9500
O2—C7	1.228 (3)	C6—C7	1.493 (4)
N1—C7	1.376 (4)	C9—C10	1.523 (4)
N1—C8	1.397 (4)	C9—H9A	0.9900
N1—H1N1	0.80 (5)	C9—H9B	0.9900
N2—C8	1.325 (3)	C10—C11	1.519 (4)
N2—C9	1.460 (3)	C10—H10A	0.9900
N2—H1N2	0.87 (3)	C10—H10B	0.9900
N3—C11	1.335 (4)	C11—C12	1.392 (4)
N3—C15	1.351 (4)	C12—C13	1.391 (4)
C1—C2	1.376 (4)	C12—H12A	0.9500
C1—C6	1.393 (4)	C13—C14	1.374 (4)
C1—H1A	0.9500	C13—H13A	0.9500
C2—C3	1.402 (4)	C14—C15	1.386 (4)
C2—H2A	0.9500	C14—H14A	0.9500
C3—C4	1.390 (4)	C15—H15A	0.9500
C3—C16	1.502 (4)	C16—H16C	0.9800
C4—C5	1.391 (4)	C16—H16D	0.9800
C4—H4A	0.9500	C16—H16A	0.9800
C5—C6	1.399 (4)
C7—N1—C8	128.8 (2)	N2—C9—H9A	109.5
C7—N1—H1N1	119 (3)	C10—C9—H9A	109.5
C8—N1—H1N1	111 (3)	N2—C9—H9B	109.5
C8—N2—C9	125.0 (2)	C10—C9—H9B	109.5
C8—N2—H1N2	113 (2)	H9A—C9—H9B	108.1
C9—N2—H1N2	121 (2)	C11—C10—C9	114.1 (2)
C11—N3—C15	117.7 (3)	C11—C10—H10A	108.7
C2—C1—C6	121.1 (3)	C9—C10—H10A	108.7
C2—C1—H1A	119.4	C11—C10—H10B	108.7
C6—C1—H1A	119.4	C9—C10—H10B	108.7
C1—C2—C3	120.9 (3)	H10A—C10—H10B	107.6
C1—C2—H2A	119.5	N3—C11—C12	122.6 (3)
C3—C2—H2A	119.5	N3—C11—C10	117.9 (3)
C4—C3—C2	117.8 (3)	C12—C11—C10	119.5 (3)
C4—C3—C16	121.4 (3)	C13—C12—C11	118.7 (3)
C2—C3—C16	120.8 (3)	C13—C12—H12A	120.6
C3—C4—C5	121.8 (3)	C11—C12—H12A	120.6
C3—C4—H4A	119.1	C14—C13—C12	119.3 (3)
C5—C4—H4A	119.1	C14—C13—H13A	120.3
C4—C5—C6	119.7 (3)	C12—C13—H13A	120.3
C4—C5—H5A	120.2	C13—C14—C15	118.4 (3)
C6—C5—H5A	120.2	C13—C14—H14A	120.8
C1—C6—C5	118.7 (3)	C15—C14—H14A	120.8
C1—C6—C7	116.4 (2)	N3—C15—C14	123.3 (3)
C5—C6—C7	124.9 (2)	N3—C15—H15A	118.4
O2—C7—N1	122.0 (3)	C14—C15—H15A	118.4
O2—C7—C6	121.0 (3)	C3—C16—H16C	109.5
N1—C7—C6	117.0 (2)	C3—C16—H16D	109.5
N2—C8—N1	115.7 (2)	H16C—C16—H16D	109.5
N2—C8—S1	126.4 (2)	C3—C16—H16A	109.5
N1—C8—S1	117.8 (2)	H16C—C16—H16A	109.5
N2—C9—C10	110.5 (2)	H16D—C16—H16A	109.5
C6—C1—C2—C3	−0.5 (5)	C9—N2—C8—N1	173.5 (3)
C1—C2—C3—C4	1.0 (4)	C9—N2—C8—S1	−6.9 (4)
C1—C2—C3—C16	−178.7 (3)	C7—N1—C8—N2	−4.4 (4)
C2—C3—C4—C5	−0.9 (4)	C7—N1—C8—S1	175.9 (2)
C16—C3—C4—C5	178.8 (3)	C8—N2—C9—C10	−98.0 (3)
C3—C4—C5—C6	0.4 (4)	N2—C9—C10—C11	−63.9 (3)
C2—C1—C6—C5	−0.1 (4)	C15—N3—C11—C12	−1.0 (4)
C2—C1—C6—C7	179.8 (3)	C15—N3—C11—C10	177.2 (3)
C4—C5—C6—C1	0.1 (4)	C9—C10—C11—N3	1.1 (4)
C4—C5—C6—C7	−179.7 (3)	C9—C10—C11—C12	179.4 (3)
C8—N1—C7—O2	2.1 (5)	N3—C11—C12—C13	1.5 (4)
C8—N1—C7—C6	−178.7 (3)	C10—C11—C12—C13	−176.6 (3)
C1—C6—C7—O2	0.8 (4)	C11—C12—C13—C14	−0.5 (4)
C5—C6—C7—O2	−179.3 (3)	C12—C13—C14—C15	−0.9 (4)
C1—C6—C7—N1	−178.3 (3)	C11—N3—C15—C14	−0.5 (4)
C5—C6—C7—N1	1.5 (4)	C13—C14—C15—N3	1.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O2	0.87 (4)	1.90 (3)	2.645 (3)	143 (3)
N2—H1N2···N3	0.87 (4)	2.41 (4)	2.860 (4)	113 (3)
C1—H1A···O2	0.95	2.42	2.751 (4)	100
C9—H9B···S1	0.99	2.72	3.166 (4)	108
C14—H14A···O2i	0.95	2.51	3.421 (4)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O2	0.87 (4)	1.90 (3)	2.645 (3)	143 (3)
C14—H14A⋯O2i	0.95	2.51	3.421 (4)	161

Symmetry code: (i) .