N-Benzyl-pyridine-2-sulfonamide.

The title compound, C(12)H(12)N(2)O(2)S, was obtained by the reaction of 2-mercaptopyridine and benzyl-amine. The dihedral angle between the benzene and pyridine rings is 75.75 (9)°. In the crystal, mol-ecules are linked into chains along the c axis by N-H⋯O and N-H⋯N hydrogen bonds; the chains are cross-linked into a two-dimensional network parallel to the bc plane via C-H⋯O hydrogen bonds.

Related literature

For the synthesis, see: Wright et al. (2006 ▶). For applications of sulfonamides, see: Connor (1998 ▶). For the structure of N-benzyl­quinoline-8-sulfonamide, see: Andrighetti-Fröhner et al. (2006 ▶).

Experimental

Crystal data

C12H12N2O2S

M = 248.30

Monoclinic,

a = 11.099 (2) Å

b = 10.709 (2) Å

c = 9.513 (2) Å

β = 91.893 (4)°

V = 1130.1 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 173 K

0.50 × 0.20 × 0.18 mm

Data collection

Bruker SMART APEX area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.823, T max = 1.00 (expected range = 0.783–0.951)

5922 measured reflections

2195 independent reflections

2078 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.101

S = 1.00

2195 reflections

157 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.40 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809018054/ci2800sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018054/ci2800Isup2.hkl

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

C12H12N2O2S	F(000) = 520
Mr = 248.30	Dx = 1.459 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4484 reflections
a = 11.099 (2) Å	θ = 2.6–28.2°
b = 10.709 (2) Å	µ = 0.28 mm−1
c = 9.513 (2) Å	T = 173 K
β = 91.893 (4)°	Needle, colourless
V = 1130.1 (4) Å3	0.50 × 0.20 × 0.18 mm
Z = 4

Bruker SMART APEX area-detector diffractometer	2195 independent reflections
Radiation source: fine-focus sealed tube	2078 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 26.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −12→13
Tmin = 0.823, Tmax = 1.00	k = −11→13
5922 measured reflections	l = −11→11

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0567P)2 + 0.7208P] where P = (Fo2 + 2Fc2)/3
2195 reflections	(Δ/σ)max = 0.001
157 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.40 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	0.29480 (4)	0.35956 (4)	−0.07138 (4)	0.02300 (15)
O1	0.23235 (11)	0.37287 (12)	−0.20382 (13)	0.0297 (3)
O2	0.35175 (11)	0.46543 (11)	−0.00687 (13)	0.0303 (3)
N1	0.20157 (13)	0.30466 (14)	0.03864 (16)	0.0247 (3)
H1	0.2331 (19)	0.299 (2)	0.118 (2)	0.030*
N2	0.37751 (14)	0.15428 (14)	−0.18353 (16)	0.0288 (3)
C1	0.40853 (15)	0.24506 (16)	−0.09461 (17)	0.0242 (4)
C2	0.51786 (16)	0.25414 (18)	−0.02210 (19)	0.0296 (4)
H2	0.5353	0.3219	0.0397	0.036*
C3	0.60085 (17)	0.16046 (19)	−0.0433 (2)	0.0336 (4)
H3	0.6775	0.1622	0.0041	0.040*
C4	0.57087 (17)	0.06477 (18)	−0.13383 (19)	0.0332 (4)
H4	0.6264	−0.0009	−0.1497	0.040*
C5	0.45909 (17)	0.06519 (18)	−0.20149 (19)	0.0329 (4)
H5	0.4393	−0.0014	−0.2640	0.039*
C6	0.11909 (16)	0.20325 (17)	−0.00404 (19)	0.0297 (4)
H6A	0.1627	0.1226	0.0006	0.036*
H6B	0.0903	0.2166	−0.1025	0.036*
C7	0.01310 (15)	0.19830 (16)	0.09002 (17)	0.0240 (4)
C8	−0.01617 (16)	0.08823 (16)	0.15529 (19)	0.0274 (4)
H8	0.0322	0.0162	0.1424	0.033*
C9	−0.11535 (16)	0.08132 (18)	0.23949 (19)	0.0321 (4)
H9	−0.1354	0.0046	0.2830	0.039*
C10	−0.18463 (17)	0.18527 (19)	0.2601 (2)	0.0345 (4)
H10	−0.2523	0.1809	0.3185	0.041*
C11	−0.15598 (17)	0.29609 (18)	0.1958 (2)	0.0353 (4)
H11	−0.2037	0.3683	0.2104	0.042*
C12	−0.05840 (17)	0.30255 (17)	0.1105 (2)	0.0301 (4)
H12	−0.0399	0.3790	0.0653	0.036*

	U11	U22	U33	U12	U13	U23
S1	0.0240 (2)	0.0224 (2)	0.0226 (2)	−0.00314 (15)	0.00148 (16)	0.00164 (15)
O1	0.0300 (6)	0.0336 (7)	0.0254 (7)	−0.0023 (5)	−0.0006 (5)	0.0055 (5)
O2	0.0312 (6)	0.0233 (6)	0.0364 (7)	−0.0054 (5)	−0.0001 (5)	0.0000 (5)
N1	0.0253 (7)	0.0274 (8)	0.0215 (7)	−0.0047 (6)	0.0020 (6)	−0.0024 (6)
N2	0.0323 (8)	0.0296 (8)	0.0245 (8)	−0.0012 (6)	0.0005 (6)	−0.0012 (6)
C1	0.0248 (8)	0.0264 (8)	0.0215 (8)	−0.0040 (7)	0.0046 (6)	0.0024 (6)
C2	0.0260 (9)	0.0326 (9)	0.0303 (9)	−0.0045 (7)	0.0012 (7)	0.0000 (7)
C3	0.0259 (9)	0.0405 (10)	0.0346 (10)	−0.0009 (8)	0.0040 (7)	0.0058 (8)
C4	0.0355 (10)	0.0352 (10)	0.0295 (9)	0.0068 (8)	0.0098 (7)	0.0040 (8)
C5	0.0415 (10)	0.0307 (9)	0.0266 (9)	0.0020 (8)	0.0039 (8)	−0.0030 (7)
C6	0.0315 (9)	0.0287 (9)	0.0293 (9)	−0.0085 (7)	0.0084 (7)	−0.0066 (7)
C7	0.0233 (8)	0.0270 (8)	0.0217 (8)	−0.0053 (7)	0.0000 (6)	−0.0029 (6)
C8	0.0276 (8)	0.0240 (8)	0.0306 (9)	−0.0019 (7)	0.0003 (7)	−0.0022 (7)
C9	0.0340 (9)	0.0310 (9)	0.0315 (9)	−0.0079 (8)	0.0042 (7)	0.0035 (8)
C10	0.0275 (9)	0.0421 (11)	0.0343 (10)	−0.0065 (8)	0.0088 (7)	−0.0059 (8)
C11	0.0292 (9)	0.0331 (10)	0.0438 (11)	0.0038 (8)	0.0020 (8)	−0.0049 (8)
C12	0.0329 (9)	0.0251 (9)	0.0323 (9)	−0.0015 (7)	−0.0008 (7)	0.0022 (7)

S1—O1	1.4249 (13)	C5—H5	0.95
S1—O2	1.4268 (13)	C6—C7	1.502 (2)
S1—N1	1.6073 (15)	C6—H6A	0.99
S1—C1	1.7787 (18)	C6—H6B	0.99
N1—C6	1.469 (2)	C7—C8	1.376 (2)
N1—H1	0.82 (2)	C7—C12	1.387 (3)
N2—C1	1.327 (2)	C8—C9	1.385 (3)
N2—C5	1.330 (2)	C8—H8	0.95
C1—C2	1.379 (2)	C9—C10	1.371 (3)
C2—C3	1.381 (3)	C9—H9	0.95
C2—H2	0.95	C10—C11	1.377 (3)
C3—C4	1.373 (3)	C10—H10	0.95
C3—H3	0.95	C11—C12	1.376 (3)
C4—C5	1.379 (3)	C11—H11	0.95
C4—H4	0.95	C12—H12	0.95
O1—S1—O2	119.76 (8)	N1—C6—C7	110.77 (14)
O1—S1—N1	107.91 (8)	N1—C6—H6A	109.5
O2—S1—N1	107.23 (8)	C7—C6—H6A	109.5
O1—S1—C1	106.59 (8)	N1—C6—H6B	109.5
O2—S1—C1	107.16 (8)	C7—C6—H6B	109.5
N1—S1—C1	107.67 (8)	H6A—C6—H6B	108.1
C6—N1—S1	119.95 (12)	C8—C7—C12	118.78 (16)
C6—N1—H1	116.0 (15)	C8—C7—C6	120.01 (16)
S1—N1—H1	111.2 (15)	C12—C7—C6	121.20 (16)
C1—N2—C5	116.37 (15)	C7—C8—C9	120.72 (17)
N2—C1—C2	125.17 (17)	C7—C8—H8	119.6
N2—C1—S1	114.46 (13)	C9—C8—H8	119.6
C2—C1—S1	120.36 (14)	C10—C9—C8	119.98 (17)
C1—C2—C3	117.12 (17)	C10—C9—H9	120.0
C1—C2—H2	121.4	C8—C9—H9	120.0
C3—C2—H2	121.4	C9—C10—C11	119.85 (18)
C4—C3—C2	119.00 (18)	C9—C10—H10	120.1
C4—C3—H3	120.5	C11—C10—H10	120.1
C2—C3—H3	120.5	C12—C11—C10	120.18 (18)
C3—C4—C5	119.10 (18)	C12—C11—H11	119.9
C3—C4—H4	120.5	C10—C11—H11	119.9
C5—C4—H4	120.5	C11—C12—C7	120.48 (17)
N2—C5—C4	123.24 (17)	C11—C12—H12	119.8
N2—C5—H5	118.4	C7—C12—H12	119.8
C4—C5—H5	118.4
O1—S1—N1—C6	42.85 (16)	C2—C3—C4—C5	0.3 (3)
O2—S1—N1—C6	173.12 (13)	C1—N2—C5—C4	−0.4 (3)
C1—S1—N1—C6	−71.85 (15)	C3—C4—C5—N2	−0.1 (3)
C5—N2—C1—C2	0.8 (3)	S1—N1—C6—C7	−159.20 (13)
C5—N2—C1—S1	−178.54 (13)	N1—C6—C7—C8	−126.83 (17)
O1—S1—C1—N2	−34.71 (14)	N1—C6—C7—C12	54.6 (2)
O2—S1—C1—N2	−164.06 (12)	C12—C7—C8—C9	0.2 (3)
N1—S1—C1—N2	80.87 (14)	C6—C7—C8—C9	−178.38 (16)
O1—S1—C1—C2	145.94 (14)	C7—C8—C9—C10	−0.9 (3)
O2—S1—C1—C2	16.58 (16)	C8—C9—C10—C11	0.6 (3)
N1—S1—C1—C2	−98.49 (15)	C9—C10—C11—C12	0.3 (3)
N2—C1—C2—C3	−0.6 (3)	C10—C11—C12—C7	−1.0 (3)
S1—C1—C2—C3	178.71 (13)	C8—C7—C12—C11	0.7 (3)
C1—C2—C3—C4	0.0 (3)	C6—C7—C12—C11	179.29 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2i	0.82 (2)	2.49 (2)	3.264 (2)	157 (2)
N1—H1···O1i	0.82 (2)	2.50 (2)	3.111 (2)	132 (2)
C4—H4···O1ii	0.95	2.52	3.406 (2)	154
C5—H5···O2iii	0.95	2.51	3.121 (2)	122

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N2i	0.82 (2)	2.49 (2)	3.264 (2)	157 (2)
N1—H1⋯O1i	0.82 (2)	2.50 (2)	3.111 (2)	132 (2)
C4—H4⋯O1ii	0.95	2.52	3.406 (2)	154
C5—H5⋯O2iii	0.95	2.51	3.121 (2)	122

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