N-(4-Chloro-pyridin-2-yl)-N-(4-methyl-phenyl-sulfon-yl)acetamide.

The crystal structure of the title compound, C(14)H(13)ClN(2)O(3)S, features a three-dimensional network stabilized by inter-molecular C-H⋯O hydrogen bonds between the mol-ecules. The 4-methyl-phenyl-sulfonyl ring forms a dihedral angle of 30.6 (1)° with the 4-chloro-pyridine ring.

Related literature

For the biological activity of 2-alkyl­amino­pyridinyl or 2-acyl­amino­pyridinyl imidazole derivatives as p38α MAPK inhibitors, see: Laufer et al. (2008 ▶, 2010 ▶); Ziegler et al. (2009 ▶). For general background to protecting groups, see: Kocieński (2005 ▶). For the preparation of the N-protected 4-chloro­pyridine, see: Berliner & Belecki (2005 ▶); Sciotti et al. (2005 ▶); Shi & Wang (2002 ▶).

Experimental

Crystal data

C14H13ClN2O3S

M = 324.77

Orthorhombic,

a = 12.578 (2) Å

b = 7.5460 (8) Å

c = 30.194 (3) Å

V = 2865.7 (7) Å3

Z = 8

Cu Kα radiation

μ = 3.83 mm−1

T = 193 K

0.35 × 0.35 × 0.25 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (CORINC; Dräger & Gattow, 1971 ▶) T min = 0.872, T max = 0.997

5291 measured reflections

2713 independent reflections

2412 reflections with I > 2σ(I)

R int = 0.079

3 standard reflections every 60 min intensity decay: 2%

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.129

S = 1.13

2713 reflections

193 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.33 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: CORINC (Dräger & Gattow, 1971 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810048324/bt5410sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048324/bt5410Isup2.hkl

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

C14H13ClN2O3S	F(000) = 1344
Mr = 324.77	Dx = 1.506 Mg m−3
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 25 reflections
a = 12.578 (2) Å	θ = 65–69°
b = 7.5460 (8) Å	µ = 3.83 mm−1
c = 30.194 (3) Å	T = 193 K
V = 2865.7 (7) Å3	Block, colourless
Z = 8	0.35 × 0.35 × 0.25 mm

Enraf–Nonius CAD-4 diffractometer	2412 reflections with I > 2σ(I)
Radiation source: rotating anode	Rint = 0.079
graphite	θmax = 70.0°, θmin = 2.9°
ω/2θ scans	h = −15→15
Absorption correction: ψ scan (CORINC; Dräger & Gattow, 1971)	k = 0→9
Tmin = 0.872, Tmax = 0.997	l = 0→36
5291 measured reflections	3 standard reflections every 60 min
2713 independent reflections	intensity decay: 2%

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049	H-atom parameters constrained
wR(F2) = 0.129	w = 1/[σ2(Fo2) + (0.0592P)2 + 0.6955P] where P = (Fo2 + 2Fc2)/3
S = 1.13	(Δ/σ)max = 0.001
2713 reflections	Δρmax = 0.44 e Å−3
193 parameters	Δρmin = −0.33 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00129 (16)

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
Cl1	0.26049 (7)	0.59127 (8)	0.519895 (18)	0.0474 (2)
C1	0.55234 (19)	0.0478 (3)	0.36074 (7)	0.0279 (5)
C2	0.5457 (2)	−0.0380 (3)	0.31992 (7)	0.0299 (5)
H2	0.4787	−0.0702	0.3079	0.036*
C3	0.6385 (2)	−0.0751 (3)	0.29725 (7)	0.0358 (6)
H3	0.6346	−0.1337	0.2694	0.043*
C4	0.7371 (2)	−0.0290 (3)	0.31410 (8)	0.0374 (6)
C5	0.7421 (2)	0.0548 (3)	0.35535 (8)	0.0379 (5)
H5	0.8093	0.0851	0.3675	0.046*
C6	0.6503 (2)	0.0940 (3)	0.37862 (7)	0.0342 (5)
H6	0.6542	0.1519	0.4065	0.041*
C7	0.8367 (3)	−0.0685 (4)	0.28847 (11)	0.0545 (8)
H7A	0.8945	−0.0963	0.3091	0.082*
H7B	0.8562	0.0351	0.2707	0.082*
H7C	0.8243	−0.1700	0.2689	0.082*
S8	0.43683 (5)	0.09319 (7)	0.390620 (16)	0.0289 (2)
O9	0.46215 (17)	0.0989 (2)	0.43669 (5)	0.0394 (4)
O10	0.35394 (15)	−0.0198 (2)	0.37556 (5)	0.0390 (4)
N11	0.40466 (17)	0.3056 (2)	0.37834 (6)	0.0295 (4)
C12	0.38183 (19)	0.3544 (3)	0.33447 (7)	0.0314 (5)
O13	0.37972 (16)	0.2443 (2)	0.30578 (5)	0.0404 (4)
C14	0.3638 (3)	0.5483 (3)	0.32551 (8)	0.0451 (6)
H14A	0.4324	0.6097	0.3245	0.068*
H14B	0.3201	0.5990	0.3492	0.068*
H14C	0.3273	0.5623	0.2971	0.068*
C15	0.41589 (19)	0.4361 (3)	0.41287 (6)	0.0270 (5)
C16	0.33884 (19)	0.4476 (3)	0.44486 (6)	0.0278 (4)
H16	0.2787	0.3713	0.4447	0.033*
C17	0.3522 (2)	0.5750 (3)	0.47748 (7)	0.0305 (5)
C18	0.4390 (2)	0.6871 (3)	0.47593 (8)	0.0373 (6)
H18	0.4488	0.7773	0.4975	0.045*
C19	0.5105 (2)	0.6634 (3)	0.44216 (8)	0.0389 (6)
H19	0.5704	0.7400	0.4411	0.047*
N20	0.50149 (17)	0.5390 (3)	0.41048 (6)	0.0343 (4)

	U11	U22	U33	U12	U13	U23
Cl1	0.0655 (5)	0.0449 (4)	0.0320 (3)	0.0135 (3)	0.0132 (3)	−0.0045 (2)
C1	0.0379 (13)	0.0247 (10)	0.0211 (9)	0.0010 (9)	−0.0010 (8)	0.0012 (8)
C2	0.0408 (13)	0.0237 (10)	0.0251 (10)	−0.0023 (10)	−0.0025 (9)	−0.0026 (8)
C3	0.0527 (15)	0.0273 (10)	0.0274 (10)	0.0045 (11)	0.0038 (11)	−0.0014 (8)
C4	0.0440 (15)	0.0286 (11)	0.0396 (11)	0.0089 (11)	0.0078 (11)	0.0102 (9)
C5	0.0349 (13)	0.0353 (12)	0.0436 (12)	0.0010 (10)	−0.0063 (11)	0.0064 (10)
C6	0.0455 (15)	0.0296 (11)	0.0275 (10)	0.0013 (10)	−0.0086 (10)	−0.0012 (8)
C7	0.0509 (18)	0.0453 (15)	0.0675 (18)	0.0124 (14)	0.0187 (16)	0.0125 (13)
S8	0.0396 (4)	0.0244 (3)	0.0225 (3)	0.0014 (2)	0.0028 (2)	0.00126 (17)
O9	0.0628 (12)	0.0318 (8)	0.0236 (8)	0.0098 (8)	0.0048 (8)	0.0027 (6)
O10	0.0411 (10)	0.0320 (8)	0.0438 (9)	−0.0061 (8)	0.0062 (7)	0.0011 (7)
N11	0.0382 (11)	0.0257 (9)	0.0244 (8)	0.0029 (8)	0.0009 (7)	−0.0017 (7)
C12	0.0326 (12)	0.0350 (11)	0.0265 (10)	0.0013 (10)	−0.0022 (9)	0.0019 (9)
O13	0.0564 (11)	0.0390 (9)	0.0257 (7)	0.0014 (9)	−0.0055 (7)	−0.0002 (7)
C14	0.0530 (16)	0.0427 (14)	0.0397 (12)	0.0063 (13)	0.0026 (12)	0.0058 (11)
C15	0.0336 (11)	0.0252 (10)	0.0221 (9)	0.0050 (9)	−0.0035 (8)	0.0013 (7)
C16	0.0327 (11)	0.0256 (10)	0.0252 (9)	0.0019 (9)	−0.0014 (8)	0.0014 (8)
C17	0.0397 (13)	0.0281 (10)	0.0235 (9)	0.0091 (10)	−0.0021 (9)	0.0020 (8)
C18	0.0520 (15)	0.0272 (11)	0.0327 (11)	0.0039 (11)	−0.0129 (10)	−0.0039 (9)
C19	0.0379 (13)	0.0321 (12)	0.0467 (13)	−0.0030 (11)	−0.0089 (11)	0.0011 (10)
N20	0.0350 (11)	0.0315 (10)	0.0364 (10)	0.0005 (9)	−0.0008 (8)	0.0025 (8)

Cl1—C17	1.728 (2)	S8—N11	1.6942 (18)
C1—C6	1.390 (3)	N11—C12	1.405 (3)
C1—C2	1.395 (3)	N11—C15	1.441 (3)
C1—S8	1.744 (2)	C12—O13	1.201 (3)
C2—C3	1.382 (4)	C12—C14	1.505 (3)
C2—H2	0.9500	C14—H14A	0.9800
C3—C4	1.385 (4)	C14—H14B	0.9800
C3—H3	0.9500	C14—H14C	0.9800
C4—C5	1.398 (4)	C15—N20	1.329 (3)
C4—C7	1.502 (4)	C15—C16	1.371 (3)
C5—C6	1.384 (4)	C16—C17	1.387 (3)
C5—H5	0.9500	C16—H16	0.9500
C6—H6	0.9500	C17—C18	1.381 (4)
C7—H7A	0.9800	C18—C19	1.371 (4)
C7—H7B	0.9800	C18—H18	0.9500
C7—H7C	0.9800	C19—N20	1.345 (3)
S8—O10	1.4213 (19)	C19—H19	0.9500
S8—O9	1.4276 (16)
C6—C1—C2	120.8 (2)	N11—S8—C1	105.75 (10)
C6—C1—S8	119.24 (16)	C12—N11—C15	121.53 (18)
C2—C1—S8	119.92 (18)	C12—N11—S8	120.24 (15)
C3—C2—C1	118.8 (2)	C15—N11—S8	117.69 (14)
C3—C2—H2	120.6	O13—C12—N11	120.2 (2)
C1—C2—H2	120.6	O13—C12—C14	122.7 (2)
C2—C3—C4	121.5 (2)	N11—C12—C14	117.1 (2)
C2—C3—H3	119.2	C12—C14—H14A	109.5
C4—C3—H3	119.2	C12—C14—H14B	109.5
C3—C4—C5	118.8 (2)	H14A—C14—H14B	109.5
C3—C4—C7	120.5 (2)	C12—C14—H14C	109.5
C5—C4—C7	120.7 (3)	H14A—C14—H14C	109.5
C6—C5—C4	120.8 (2)	H14B—C14—H14C	109.5
C6—C5—H5	119.6	N20—C15—C16	125.0 (2)
C4—C5—H5	119.6	N20—C15—N11	116.06 (19)
C5—C6—C1	119.3 (2)	C16—C15—N11	118.9 (2)
C5—C6—H6	120.4	C15—C16—C17	117.3 (2)
C1—C6—H6	120.4	C15—C16—H16	121.4
C4—C7—H7A	109.5	C17—C16—H16	121.4
C4—C7—H7B	109.5	C18—C17—C16	119.8 (2)
H7A—C7—H7B	109.5	C18—C17—Cl1	120.60 (17)
C4—C7—H7C	109.5	C16—C17—Cl1	119.64 (19)
H7A—C7—H7C	109.5	C19—C18—C17	117.6 (2)
H7B—C7—H7C	109.5	C19—C18—H18	121.2
O10—S8—O9	119.57 (11)	C17—C18—H18	121.2
O10—S8—N11	108.79 (10)	N20—C19—C18	124.4 (2)
O9—S8—N11	103.77 (9)	N20—C19—H19	117.8
O10—S8—C1	109.13 (10)	C18—C19—H19	117.8
O9—S8—C1	108.91 (12)	C15—N20—C19	115.9 (2)
C6—C1—C2—C3	−0.5 (3)	O9—S8—N11—C15	3.9 (2)
S8—C1—C2—C3	−178.90 (16)	C1—S8—N11—C15	−110.65 (18)
C1—C2—C3—C4	−0.1 (3)	C15—N11—C12—O13	175.1 (2)
C2—C3—C4—C5	1.0 (3)	S8—N11—C12—O13	3.8 (3)
C2—C3—C4—C7	−179.1 (2)	C15—N11—C12—C14	−3.2 (3)
C3—C4—C5—C6	−1.2 (4)	S8—N11—C12—C14	−174.53 (19)
C7—C4—C5—C6	178.9 (2)	C12—N11—C15—N20	−69.5 (3)
C4—C5—C6—C1	0.6 (3)	S8—N11—C15—N20	102.1 (2)
C2—C1—C6—C5	0.3 (3)	C12—N11—C15—C16	109.6 (2)
S8—C1—C6—C5	178.69 (17)	S8—N11—C15—C16	−78.8 (2)
C6—C1—S8—O10	−158.12 (17)	N20—C15—C16—C17	−0.8 (3)
C2—C1—S8—O10	20.3 (2)	N11—C15—C16—C17	−179.85 (18)
C6—C1—S8—O9	−26.0 (2)	C15—C16—C17—C18	1.9 (3)
C2—C1—S8—O9	152.42 (17)	C15—C16—C17—Cl1	−177.71 (16)
C6—C1—S8—N11	85.00 (19)	C16—C17—C18—C19	−1.6 (3)
C2—C1—S8—N11	−96.60 (19)	Cl1—C17—C18—C19	178.00 (18)
O10—S8—N11—C12	−56.1 (2)	C17—C18—C19—N20	0.2 (4)
O9—S8—N11—C12	175.60 (19)	C16—C15—N20—C19	−0.5 (3)
C1—S8—N11—C12	61.0 (2)	N11—C15—N20—C19	178.49 (19)
O10—S8—N11—C15	132.24 (18)	C18—C19—N20—C15	0.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O13i	0.95	2.46	3.404 (3)	174
C14—H14B···O10ii	0.98	2.50	3.170 (4)	126
C18—H18···O9iii	0.95	2.46	3.334 (3)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O13i	0.95	2.46	3.404 (3)	174
C14—H14B⋯O10ii	0.98	2.50	3.170 (4)	126
C18—H18⋯O9iii	0.95	2.46	3.334 (3)	152

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