organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

N-Benzyl­pyridine-2-sulfonamide

aDepartment of Chemistry and the Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, People's Republic of China
*Correspondence e-mail: xpchen1217@163.com

(Received 7 May 2009; accepted 13 May 2009; online 29 May 2009)

The title compound, C12H12N2O2S, was obtained by the reaction of 2-mercaptopyridine and benzyl­amine. The dihedral angle between the benzene and pyridine rings is 75.75 (9)°. In the crystal, mol­ecules 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[Wright, S. W. & Hallstrom, K. N. (2006). J. Org. Chem. 71, 1080-1084.]). For applications of sulfonamides, see: Connor (1998[Connor, E. E. (1998). Prim. Care Update Ob. Gyn. 5, 32-35.]). For the structure of N-benzyl­quinoline-8-sulfonamide, see: Andrighetti-Fröhner et al. (2006[Andrighetti-Fröhner, C. R., da Silva, L. E., Nunes, R. J., Simões, C. M. O. & Foro, S. (2006). Acta Cryst. E62, o3693-o3694.]).

[Scheme 1]

Experimental

Crystal data
  • C12H12N2O2S

  • Mr = 248.30

  • Monoclinic, P 21 /c

  • 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[Bruker (2001). SAINT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.823, Tmax = 1.00 (expected range = 0.783–0.951)

  • 5922 measured reflections

  • 2195 independent reflections

  • 2078 reflections with I > 2σ(I)

  • Rint = 0.021

Refinement
  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) [-x+1, y-{\script{1\over 2}}, -z-{\script{1\over 2}}]; (iii) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: SMART (Bruker, 2001[Bruker (2001). SAINT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SAINT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

Sulfonamides are an important category of pharmaceutical compounds with a broad spectrum of biological activities, as good antibacterials, diuretics, anticonvulsants, and HIV protease inhibitors (Connor, 1998).

The molecular structure of the title compound is shown in Fig. 1. Bond lengths and angles are comparable to those observed for N-benzylquinoline-8-sulfonamide (Andrighetti-Fröhner et al., 2006). The C1—S1—N1—C6 torsion angle is -71.85 (15)°. The dihedral angle between the benzene and pyridine rings is 75.75 (9)°.

Hydrogen bonding plays a significant role in stabilizing the crystal structure; see Table 1 for geometric parameters and symmetry operations. The molecules are linked into a chain along the c axis by N—H···O and N—H···N hydrogen bonds. The chains are cross-linked via C—H···O hydrogen bonds to form a two-dimensional network parallel to the bc plane.

Related literature top

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 top

The title compound was synthesized using a similar synthetic method for the preparation of heteroaryl sulfonamides (Wright et al., 2006). 2-Mercaptopyridine (0.56 g, 5 mmol) was stirred in a mixture of 25 mL of dichloromethane and 25 mL of 1 M HCl in a 125 ml flask for 8 min at 263 to 268 K. Cold sodium hypochlorite (6% solution, 0.68 M, 26 ml, 18 mmol, 3.3 equiv) was then added dropwise with very rapid stirring, maintaining the internal temperature at 263 to 268 K. The mixture was stirred for 30 min at 263 to 268 K after the addition was completed, the mixture was transferred to a separatory funnel (pre-cooled with ice water) and the dichloromethane layer was rapidly separated and collected in a clean 125 ml flask cooled in a ice-salt bath. Benzylamine (1.1 ml, 10 mmol) was added with stirring, when the dichloromethane layer became a white suspension, the flask was removed to an ice-water bath and the suspension was stirred for 30 min at 273 K. The suspension was then washed with 1 M HCl, then with water and brine. Drying (MgSO4) and concentration afforded the title compound as a white solid with 81% yield. Single crystals of the title compound were grown in a petroleum ether-ethyl acetate solution (3:1 v/v) by slow evaporation.

Refinement top

Atom H1 was located in a difference map and its positional parameters were refined. The remaining H atoms were positioned geometrically [C-H = 0.95 Å (aromatic) and 0.99 Å (methylene)] and were included in the refinement in the riding-model approximation. The isotropic displacement parameters were set at 1.2 times Ueq of the parent atoms.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 (Sheldrick, 2008.

Figures top
[Figure 1] Fig. 1. The molecular structure of the compound, with 50% probability displacement ellipsoids (arbitrary spheres for H atoms).
N-Benzylpyridine-2-sulfonamide top
Crystal data top
C12H12N2O2SF(000) = 520
Mr = 248.30Dx = 1.459 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4484 reflections
a = 11.099 (2) Åθ = 2.6–28.2°
b = 10.709 (2) ŵ = 0.28 mm1
c = 9.513 (2) ÅT = 173 K
β = 91.893 (4)°Needle, colourless
V = 1130.1 (4) Å30.50 × 0.20 × 0.18 mm
Z = 4
Data collection top
Bruker SMART APEX area-detector
diffractometer
2195 independent reflections
Radiation source: fine-focus sealed tube2078 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
ϕ and ω scansθmax = 26.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 1213
Tmin = 0.823, Tmax = 1.00k = 1113
5922 measured reflectionsl = 1111
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101H 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 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.40 e Å3
Crystal data top
C12H12N2O2SV = 1130.1 (4) Å3
Mr = 248.30Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.099 (2) ŵ = 0.28 mm1
b = 10.709 (2) ÅT = 173 K
c = 9.513 (2) Å0.50 × 0.20 × 0.18 mm
β = 91.893 (4)°
Data collection top
Bruker SMART APEX area-detector
diffractometer
2195 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
2078 reflections with I > 2σ(I)
Tmin = 0.823, Tmax = 1.00Rint = 0.021
5922 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.101H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.32 e Å3
2195 reflectionsΔρmin = 0.40 e Å3
157 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.29480 (4)0.35956 (4)0.07138 (4)0.02300 (15)
O10.23235 (11)0.37287 (12)0.20382 (13)0.0297 (3)
O20.35175 (11)0.46543 (11)0.00687 (13)0.0303 (3)
N10.20157 (13)0.30466 (14)0.03864 (16)0.0247 (3)
H10.2331 (19)0.299 (2)0.118 (2)0.030*
N20.37751 (14)0.15428 (14)0.18353 (16)0.0288 (3)
C10.40853 (15)0.24506 (16)0.09461 (17)0.0242 (4)
C20.51786 (16)0.25414 (18)0.02210 (19)0.0296 (4)
H20.53530.32190.03970.036*
C30.60085 (17)0.16046 (19)0.0433 (2)0.0336 (4)
H30.67750.16220.00410.040*
C40.57087 (17)0.06477 (18)0.13383 (19)0.0332 (4)
H40.62640.00090.14970.040*
C50.45909 (17)0.06519 (18)0.20149 (19)0.0329 (4)
H50.43930.00140.26400.039*
C60.11909 (16)0.20325 (17)0.00404 (19)0.0297 (4)
H6A0.16270.12260.00060.036*
H6B0.09030.21660.10250.036*
C70.01310 (15)0.19830 (16)0.09002 (17)0.0240 (4)
C80.01617 (16)0.08823 (16)0.15529 (19)0.0274 (4)
H80.03220.01620.14240.033*
C90.11535 (16)0.08132 (18)0.23949 (19)0.0321 (4)
H90.13540.00460.28300.039*
C100.18463 (17)0.18527 (19)0.2601 (2)0.0345 (4)
H100.25230.18090.31850.041*
C110.15598 (17)0.29609 (18)0.1958 (2)0.0353 (4)
H110.20370.36830.21040.042*
C120.05840 (17)0.30255 (17)0.1105 (2)0.0301 (4)
H120.03990.37900.06530.036*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0240 (2)0.0224 (2)0.0226 (2)0.00314 (15)0.00148 (16)0.00164 (15)
O10.0300 (6)0.0336 (7)0.0254 (7)0.0023 (5)0.0006 (5)0.0055 (5)
O20.0312 (6)0.0233 (6)0.0364 (7)0.0054 (5)0.0001 (5)0.0000 (5)
N10.0253 (7)0.0274 (8)0.0215 (7)0.0047 (6)0.0020 (6)0.0024 (6)
N20.0323 (8)0.0296 (8)0.0245 (8)0.0012 (6)0.0005 (6)0.0012 (6)
C10.0248 (8)0.0264 (8)0.0215 (8)0.0040 (7)0.0046 (6)0.0024 (6)
C20.0260 (9)0.0326 (9)0.0303 (9)0.0045 (7)0.0012 (7)0.0000 (7)
C30.0259 (9)0.0405 (10)0.0346 (10)0.0009 (8)0.0040 (7)0.0058 (8)
C40.0355 (10)0.0352 (10)0.0295 (9)0.0068 (8)0.0098 (7)0.0040 (8)
C50.0415 (10)0.0307 (9)0.0266 (9)0.0020 (8)0.0039 (8)0.0030 (7)
C60.0315 (9)0.0287 (9)0.0293 (9)0.0085 (7)0.0084 (7)0.0066 (7)
C70.0233 (8)0.0270 (8)0.0217 (8)0.0053 (7)0.0000 (6)0.0029 (6)
C80.0276 (8)0.0240 (8)0.0306 (9)0.0019 (7)0.0003 (7)0.0022 (7)
C90.0340 (9)0.0310 (9)0.0315 (9)0.0079 (8)0.0042 (7)0.0035 (8)
C100.0275 (9)0.0421 (11)0.0343 (10)0.0065 (8)0.0088 (7)0.0059 (8)
C110.0292 (9)0.0331 (10)0.0438 (11)0.0038 (8)0.0020 (8)0.0049 (8)
C120.0329 (9)0.0251 (9)0.0323 (9)0.0015 (7)0.0008 (7)0.0022 (7)
Geometric parameters (Å, º) top
S1—O11.4249 (13)C5—H50.95
S1—O21.4268 (13)C6—C71.502 (2)
S1—N11.6073 (15)C6—H6A0.99
S1—C11.7787 (18)C6—H6B0.99
N1—C61.469 (2)C7—C81.376 (2)
N1—H10.82 (2)C7—C121.387 (3)
N2—C11.327 (2)C8—C91.385 (3)
N2—C51.330 (2)C8—H80.95
C1—C21.379 (2)C9—C101.371 (3)
C2—C31.381 (3)C9—H90.95
C2—H20.95C10—C111.377 (3)
C3—C41.373 (3)C10—H100.95
C3—H30.95C11—C121.376 (3)
C4—C51.379 (3)C11—H110.95
C4—H40.95C12—H120.95
O1—S1—O2119.76 (8)N1—C6—C7110.77 (14)
O1—S1—N1107.91 (8)N1—C6—H6A109.5
O2—S1—N1107.23 (8)C7—C6—H6A109.5
O1—S1—C1106.59 (8)N1—C6—H6B109.5
O2—S1—C1107.16 (8)C7—C6—H6B109.5
N1—S1—C1107.67 (8)H6A—C6—H6B108.1
C6—N1—S1119.95 (12)C8—C7—C12118.78 (16)
C6—N1—H1116.0 (15)C8—C7—C6120.01 (16)
S1—N1—H1111.2 (15)C12—C7—C6121.20 (16)
C1—N2—C5116.37 (15)C7—C8—C9120.72 (17)
N2—C1—C2125.17 (17)C7—C8—H8119.6
N2—C1—S1114.46 (13)C9—C8—H8119.6
C2—C1—S1120.36 (14)C10—C9—C8119.98 (17)
C1—C2—C3117.12 (17)C10—C9—H9120.0
C1—C2—H2121.4C8—C9—H9120.0
C3—C2—H2121.4C9—C10—C11119.85 (18)
C4—C3—C2119.00 (18)C9—C10—H10120.1
C4—C3—H3120.5C11—C10—H10120.1
C2—C3—H3120.5C12—C11—C10120.18 (18)
C3—C4—C5119.10 (18)C12—C11—H11119.9
C3—C4—H4120.5C10—C11—H11119.9
C5—C4—H4120.5C11—C12—C7120.48 (17)
N2—C5—C4123.24 (17)C11—C12—H12119.8
N2—C5—H5118.4C7—C12—H12119.8
C4—C5—H5118.4
O1—S1—N1—C642.85 (16)C2—C3—C4—C50.3 (3)
O2—S1—N1—C6173.12 (13)C1—N2—C5—C40.4 (3)
C1—S1—N1—C671.85 (15)C3—C4—C5—N20.1 (3)
C5—N2—C1—C20.8 (3)S1—N1—C6—C7159.20 (13)
C5—N2—C1—S1178.54 (13)N1—C6—C7—C8126.83 (17)
O1—S1—C1—N234.71 (14)N1—C6—C7—C1254.6 (2)
O2—S1—C1—N2164.06 (12)C12—C7—C8—C90.2 (3)
N1—S1—C1—N280.87 (14)C6—C7—C8—C9178.38 (16)
O1—S1—C1—C2145.94 (14)C7—C8—C9—C100.9 (3)
O2—S1—C1—C216.58 (16)C8—C9—C10—C110.6 (3)
N1—S1—C1—C298.49 (15)C9—C10—C11—C120.3 (3)
N2—C1—C2—C30.6 (3)C10—C11—C12—C71.0 (3)
S1—C1—C2—C3178.71 (13)C8—C7—C12—C110.7 (3)
C1—C2—C3—C40.0 (3)C6—C7—C12—C11179.29 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N2i0.82 (2)2.49 (2)3.264 (2)157 (2)
N1—H1···O1i0.82 (2)2.50 (2)3.111 (2)132 (2)
C4—H4···O1ii0.952.523.406 (2)154
C5—H5···O2iii0.952.513.121 (2)122
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x+1, y1/2, z1/2; (iii) x, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC12H12N2O2S
Mr248.30
Crystal system, space groupMonoclinic, P21/c
Temperature (K)173
a, b, c (Å)11.099 (2), 10.709 (2), 9.513 (2)
β (°) 91.893 (4)
V3)1130.1 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.28
Crystal size (mm)0.50 × 0.20 × 0.18
Data collection
DiffractometerBruker SMART APEX area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.823, 1.00
No. of measured, independent and
observed [I > 2σ(I)] reflections
5922, 2195, 2078
Rint0.021
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.101, 1.00
No. of reflections2195
No. of parameters157
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.32, 0.40

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), SHELXL97 (Sheldrick, 2008.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N2i0.82 (2)2.49 (2)3.264 (2)157 (2)
N1—H1···O1i0.82 (2)2.50 (2)3.111 (2)132 (2)
C4—H4···O1ii0.952.523.406 (2)154
C5—H5···O2iii0.952.513.121 (2)122
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x+1, y1/2, z1/2; (iii) x, y+1/2, z1/2.
 

Acknowledgements

The authors thank the National Science Foundation of China (grant No. 20802060) for supporting this work.

References

First citationAndrighetti-Fröhner, C. R., da Silva, L. E., Nunes, R. J., Simões, C. M. O. & Foro, S. (2006). Acta Cryst. E62, o3693–o3694.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationBruker (2001). SAINT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationConnor, E. E. (1998). Prim. Care Update Ob. Gyn. 5, 32–35.  CrossRef Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWright, S. W. & Hallstrom, K. N. (2006). J. Org. Chem. 71, 1080–1084.  Web of Science CrossRef PubMed CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds