N-(4-Chloro-pyridin-2-yl)-N-meth-oxy-methyl-4-methyl-benzene-sulfonamide.

In the crystal structure of the title compound, C(14)H(15)ClN(2)O(3)S, each mol-ecule is connected via inter-molecular C-H⋯O hydrogen bonds to three further mol-ecules, generating a three-dimensional network. The 4-methyl-phenyl-sulfonyl ring forms a dihedral angle of 40.7 (2)° 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

C14H15ClN2O3S

M = 326.79

Orthorhombic,

a = 15.1651 (10) Å

b = 22.7953 (13) Å

c = 8.9132 (6) Å

V = 3081.2 (3) Å3

Z = 8

Cu Kα radiation

μ = 3.57 mm−1

T = 193 K

0.30 × 0.30 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (CORINC; Dräger & Gattow, 1971 ▶) T min = 0.736, T max = 0.999

2950 measured reflections

2742 independent reflections

2659 reflections with I > 2σ(I)

R int = 0.080

3 standard reflections every 60 min intensity decay: 2%

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.158

S = 1.11

2742 reflections

192 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.66 e Å−3

Δρmin = −0.53 e Å−3

Absolute structure: Flack (1983 ▶), 1176 Friedel pairs

Flack parameter: 0.02 (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/S1600536810048336/bt5411sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048336/bt5411Isup2.hkl

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

C14H15ClN2O3S	F(000) = 1360
Mr = 326.79	Dx = 1.409 Mg m−3
Orthorhombic, Aba2	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: A 2 -2ac	Cell parameters from 25 reflections
a = 15.1651 (10) Å	θ = 65–69°
b = 22.7953 (13) Å	µ = 3.57 mm−1
c = 8.9132 (6) Å	T = 193 K
V = 3081.2 (3) Å3	Block, colourless
Z = 8	0.30 × 0.30 × 0.20 mm

Enraf–Nonius CAD-4 diffractometer	2659 reflections with I > 2σ(I)
Radiation source: rotating anode	Rint = 0.080
graphite	θmax = 70.0°, θmin = 3.9°
ω/2θ scans	h = −18→18
Absorption correction: ψ scan (CORINC; Dräger & Gattow, 1971)	k = −27→27
Tmin = 0.736, Tmax = 0.999	l = −10→10
2950 measured reflections	3 standard reflections every 60 min
2742 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)] = 0.053	H-atom parameters constrained
wR(F2) = 0.158	w = 1/[σ2(Fo2) + (0.1234P)2 + 0.8389P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max < 0.001
2742 reflections	Δρmax = 0.66 e Å−3
192 parameters	Δρmin = −0.53 e Å−3
1 restraint	Absolute structure: Flack (1983), 1176 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.02 (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
Cl1	0.64226 (5)	0.45727 (4)	0.66220 (13)	0.0400 (3)
C1	0.3696 (2)	0.29193 (14)	0.2257 (4)	0.0283 (7)
C2	0.4078 (2)	0.25319 (17)	0.3272 (5)	0.0367 (8)
H2	0.4671	0.2585	0.3591	0.044*
C3	0.3586 (3)	0.20715 (17)	0.3805 (5)	0.0386 (9)
H3	0.3854	0.1794	0.4457	0.046*
C4	0.2699 (2)	0.20019 (15)	0.3411 (5)	0.0350 (8)
C5	0.2336 (2)	0.23969 (15)	0.2376 (5)	0.0379 (8)
H5	0.1739	0.2351	0.2075	0.045*
C6	0.2828 (2)	0.28515 (14)	0.1785 (5)	0.0336 (8)
H6	0.2578	0.3112	0.1071	0.040*
C7	0.2156 (3)	0.15130 (19)	0.4026 (6)	0.0501 (11)
H7A	0.2187	0.1517	0.5124	0.075*
H7B	0.2382	0.1138	0.3650	0.075*
H7C	0.1542	0.1562	0.3709	0.075*
S8	0.42918 (6)	0.35362 (4)	0.16453 (10)	0.0329 (3)
O9	0.52102 (18)	0.34292 (13)	0.1894 (4)	0.0468 (8)
O10	0.3980 (2)	0.37013 (14)	0.0185 (3)	0.0487 (8)
N11	0.40200 (19)	0.40858 (12)	0.2779 (3)	0.0267 (6)
C12	0.3183 (2)	0.43980 (16)	0.2508 (4)	0.0331 (8)
H12A	0.2907	0.4244	0.1582	0.040*
H12B	0.2774	0.4321	0.3352	0.040*
O13	0.33051 (19)	0.49934 (12)	0.2365 (4)	0.0437 (7)
C14	0.3640 (3)	0.5145 (2)	0.0901 (7)	0.0544 (12)
H14B	0.3211	0.5028	0.0134	0.082*
H14A	0.4198	0.4940	0.0727	0.082*
H14C	0.3736	0.5569	0.0847	0.082*
C15	0.4331 (2)	0.40624 (14)	0.4291 (4)	0.0246 (7)
C16	0.5156 (2)	0.42870 (12)	0.4611 (4)	0.0243 (6)
H16	0.5525	0.4442	0.3847	0.029*
C17	0.5417 (2)	0.42749 (14)	0.6091 (4)	0.0290 (7)
C18	0.4872 (3)	0.40358 (17)	0.7178 (4)	0.0344 (8)
H18	0.5044	0.4021	0.8202	0.041*
C19	0.4068 (2)	0.38197 (16)	0.6710 (5)	0.0350 (8)
H19	0.3691	0.3651	0.7445	0.042*
N20	0.3782 (2)	0.38313 (13)	0.5288 (4)	0.0316 (6)

	U11	U22	U33	U12	U13	U23
Cl1	0.0311 (4)	0.0470 (5)	0.0418 (5)	−0.0051 (3)	−0.0052 (4)	−0.0089 (4)
C1	0.0281 (16)	0.0298 (15)	0.0271 (17)	−0.0020 (12)	0.0027 (14)	−0.0038 (13)
C2	0.0302 (16)	0.0454 (19)	0.0343 (18)	0.0061 (14)	−0.0061 (17)	−0.0020 (16)
C3	0.043 (2)	0.0359 (18)	0.037 (2)	0.0076 (15)	−0.0078 (16)	0.0010 (16)
C4	0.0405 (19)	0.0314 (16)	0.0332 (19)	−0.0040 (14)	−0.0020 (18)	−0.0023 (14)
C5	0.0307 (18)	0.0373 (17)	0.046 (2)	−0.0041 (14)	−0.0032 (18)	−0.0027 (17)
C6	0.0341 (16)	0.0329 (15)	0.0337 (19)	−0.0008 (12)	−0.0088 (17)	0.0037 (15)
C7	0.062 (3)	0.043 (2)	0.045 (3)	−0.0116 (19)	−0.001 (2)	0.0057 (18)
S8	0.0347 (4)	0.0401 (4)	0.0238 (4)	−0.0081 (3)	0.0091 (4)	−0.0037 (4)
O9	0.0299 (12)	0.0588 (16)	0.052 (2)	−0.0067 (12)	0.0168 (12)	−0.0185 (14)
O10	0.067 (2)	0.0595 (17)	0.0194 (13)	−0.0161 (16)	0.0044 (14)	0.0030 (12)
N11	0.0291 (13)	0.0324 (13)	0.0188 (13)	−0.0033 (10)	−0.0015 (11)	0.0028 (11)
C12	0.0265 (16)	0.0472 (19)	0.0255 (17)	0.0007 (14)	−0.0053 (16)	0.0013 (15)
O13	0.0439 (15)	0.0426 (14)	0.0445 (16)	0.0048 (12)	−0.0128 (15)	−0.0027 (13)
C14	0.050 (3)	0.043 (2)	0.070 (3)	−0.0053 (17)	−0.002 (2)	0.018 (2)
C15	0.0253 (15)	0.0247 (15)	0.0239 (16)	0.0003 (11)	0.0014 (13)	−0.0018 (12)
C16	0.0252 (14)	0.0250 (14)	0.0226 (15)	−0.0002 (11)	0.0027 (13)	0.0016 (13)
C17	0.0258 (14)	0.0288 (14)	0.0326 (18)	0.0019 (13)	−0.0004 (15)	−0.0028 (13)
C18	0.0368 (19)	0.047 (2)	0.0200 (15)	0.0022 (15)	0.0022 (15)	0.0020 (15)
C19	0.0340 (17)	0.0465 (18)	0.0245 (17)	−0.0017 (14)	0.0047 (18)	0.0043 (17)
N20	0.0295 (13)	0.0381 (14)	0.0273 (16)	−0.0027 (12)	0.0009 (13)	0.0052 (13)

Cl1—C17	1.736 (4)	N11—C15	1.429 (4)
C1—C6	1.391 (5)	N11—C12	1.475 (4)
C1—C2	1.391 (5)	C12—O13	1.376 (5)
C1—S8	1.758 (3)	C12—H12A	0.9900
C2—C3	1.372 (6)	C12—H12B	0.9900
C2—H2	0.9500	O13—C14	1.442 (6)
C3—C4	1.400 (5)	C14—H14B	0.9800
C3—H3	0.9500	C14—H14A	0.9800
C4—C5	1.402 (6)	C14—H14C	0.9800
C4—C7	1.490 (5)	C15—N20	1.327 (5)
C5—C6	1.381 (5)	C15—C16	1.381 (4)
C5—H5	0.9500	C16—C17	1.378 (5)
C6—H6	0.9500	C16—H16	0.9500
C7—H7A	0.9800	C17—C18	1.385 (5)
C7—H7B	0.9800	C18—C19	1.380 (5)
C7—H7C	0.9800	C18—H18	0.9500
S8—O9	1.431 (3)	C19—N20	1.340 (5)
S8—O10	1.435 (3)	C19—H19	0.9500
S8—N11	1.662 (3)
C6—C1—C2	121.4 (3)	C15—N11—S8	117.6 (2)
C6—C1—S8	118.8 (3)	C12—N11—S8	118.5 (2)
C2—C1—S8	119.7 (3)	O13—C12—N11	112.0 (3)
C3—C2—C1	119.0 (3)	O13—C12—H12A	109.2
C3—C2—H2	120.5	N11—C12—H12A	109.2
C1—C2—H2	120.5	O13—C12—H12B	109.2
C2—C3—C4	121.5 (4)	N11—C12—H12B	109.2
C2—C3—H3	119.3	H12A—C12—H12B	107.9
C4—C3—H3	119.3	C12—O13—C14	111.6 (3)
C3—C4—C5	118.1 (3)	O13—C14—H14B	109.5
C3—C4—C7	121.6 (4)	O13—C14—H14A	109.5
C5—C4—C7	120.3 (4)	H14B—C14—H14A	109.5
C6—C5—C4	121.4 (3)	O13—C14—H14C	109.5
C6—C5—H5	119.3	H14B—C14—H14C	109.5
C4—C5—H5	119.3	H14A—C14—H14C	109.5
C5—C6—C1	118.7 (3)	N20—C15—C16	125.3 (3)
C5—C6—H6	120.7	N20—C15—N11	116.1 (3)
C1—C6—H6	120.7	C16—C15—N11	118.7 (3)
C4—C7—H7A	109.5	C17—C16—C15	116.8 (3)
C4—C7—H7B	109.5	C17—C16—H16	121.6
H7A—C7—H7B	109.5	C15—C16—H16	121.6
C4—C7—H7C	109.5	C16—C17—C18	120.4 (3)
H7A—C7—H7C	109.5	C16—C17—Cl1	120.4 (3)
H7B—C7—H7C	109.5	C18—C17—Cl1	119.2 (3)
O9—S8—O10	120.4 (2)	C19—C18—C17	117.1 (3)
O9—S8—N11	106.00 (16)	C19—C18—H18	121.4
O10—S8—N11	105.79 (18)	C17—C18—H18	121.4
O9—S8—C1	108.41 (18)	N20—C19—C18	124.4 (3)
O10—S8—C1	108.76 (18)	N20—C19—H19	117.8
N11—S8—C1	106.68 (15)	C18—C19—H19	117.8
C15—N11—C12	117.2 (3)	C15—N20—C19	116.0 (3)
C6—C1—C2—C3	0.5 (6)	O10—S8—N11—C12	35.5 (3)
S8—C1—C2—C3	176.2 (3)	C1—S8—N11—C12	−80.2 (3)
C1—C2—C3—C4	−3.4 (6)	C15—N11—C12—O13	83.7 (4)
C2—C3—C4—C5	3.9 (6)	S8—N11—C12—O13	−125.7 (3)
C2—C3—C4—C7	−178.1 (4)	N11—C12—O13—C14	78.1 (4)
C3—C4—C5—C6	−1.6 (6)	C12—N11—C15—N20	56.6 (4)
C7—C4—C5—C6	−179.7 (4)	S8—N11—C15—N20	−94.3 (3)
C4—C5—C6—C1	−1.1 (6)	C12—N11—C15—C16	−122.1 (3)
C2—C1—C6—C5	1.7 (6)	S8—N11—C15—C16	86.9 (3)
S8—C1—C6—C5	−174.1 (3)	N20—C15—C16—C17	−0.9 (5)
C6—C1—S8—O9	−163.5 (3)	N11—C15—C16—C17	177.7 (3)
C2—C1—S8—O9	20.7 (4)	C15—C16—C17—C18	1.2 (5)
C6—C1—S8—O10	−30.9 (3)	C15—C16—C17—Cl1	−177.5 (2)
C2—C1—S8—O10	153.3 (3)	C16—C17—C18—C19	−0.5 (5)
C6—C1—S8—N11	82.8 (3)	Cl1—C17—C18—C19	178.2 (3)
C2—C1—S8—N11	−93.0 (3)	C17—C18—C19—N20	−0.6 (6)
O9—S8—N11—C15	−45.1 (3)	C16—C15—N20—C19	−0.1 (5)
O10—S8—N11—C15	−174.0 (3)	N11—C15—N20—C19	−178.8 (3)
C1—S8—N11—C15	70.3 (3)	C18—C19—N20—C15	0.9 (6)
O9—S8—N11—C12	164.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7C···O9i	0.98	2.59	3.512 (6)	157
C16—H16···O13ii	0.95	2.56	3.485 (4)	165
C18—H18···O10iii	0.95	2.50	3.098 (5)	121
C19—H19···O10iii	0.95	2.48	3.112 (5)	124

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7C⋯O9i	0.98	2.59	3.512 (6)	157
C16—H16⋯O13ii	0.95	2.56	3.485 (4)	165
C18—H18⋯O10iii	0.95	2.50	3.098 (5)	121
C19—H19⋯O10iii	0.95	2.48	3.112 (5)	124

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