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Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): o346.
Published online 2010 January 13. doi:  10.1107/S1600536810000814
PMCID: PMC2979953

Methyl 2-(p-toluene­sulfonamido)benzoate

Abstract

The title compound, C15H15NO4S, was prepared by simple condensation of methyl 2-amino­benzoate and 4-methyl­benzene­sulfonyl chloride. The dihedral angle between the benzene rings is 84.36 (6)°. The mol­ecular structure is stabilized by an intra­molecular N—H(...)O hydrogen-bonding inter­action involving the carbonyl group as acceptor, generating an S(6) graph-set motif.

Related literature

For background information on sulfonamide derivatives and their properties, see: Sheppard et al. (2006 [triangle]). For similar structures, see: Schultz et al. (2001 [triangle]); Krishnaiah et al. (1995 [triangle]); Arshad, Khan, Shafiq et al. (2009 [triangle]); Arshad, Khan, Akkurt et al. (2009 [triangle]); Xiong et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0o346-scheme1.jpg

Experimental

Crystal data

  • C15H15NO4S
  • M r = 305.34
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o346-efi1.jpg
  • a = 15.0129 (13) Å
  • b = 8.3593 (7) Å
  • c = 11.9664 (11) Å
  • β = 96.854 (2)°
  • V = 1491.0 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.23 mm−1
  • T = 295 K
  • 0.24 × 0.16 × 0.14 mm

Data collection

  • Bruker APEXII area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003 [triangle]) T min = 0.947, T max = 0.968
  • 7663 measured reflections
  • 2639 independent reflections
  • 2230 reflections with I > 2σ(I)
  • R int = 0.024

Refinement

  • R[F 2 > 2σ(F 2)] = 0.036
  • wR(F 2) = 0.102
  • S = 1.04
  • 2639 reflections
  • 191 parameters
  • H-atom parameters constrained
  • Δρmax = 0.15 e Å−3
  • Δρmin = −0.32 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810000814/bh2263sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810000814/bh2263Isup2.hkl

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

Acknowledgments

The authors are grateful to the Natural Science Foundation of Shandong Province, China (grant No. G0231) and the Foundation of the Education Ministry of China for Returned Students (grant No. G0220) for financial support. The X-ray data were collected at Taishan University, China.

supplementary crystallographic information

Comment

Sulfur-containing compounds, such as sulfates, sulfones, thiols, sulfonamides and sulfoxides can exhibit insecticidal, germicidal or antimicrobial activities (Schultz et al., 2001; Krishnaiah et al., 1995; Arshad, Khan, Shafiq et al., 2009; Xiong et al., 2007). Particularly, the sulfonamides are biologically active organic compounds, which have been investigated as inhibitors of methionine aminopeptidase-2 (MetAP2) and intermediates for cancer therapy (Sheppard et al., 2006). In order to obtain detailed information on the molecular conformation, the X-ray study of the title sulfonamide has been carried out, and the results are presented here.

As is shown in Fig. 1, the two benzene rings are approximately orthogonal, the dihedral angle between their planes being 84.36 (6)°. In addition to van der Waals interactions, there is an intramolecular N—H···O hydrogen bond which generates a graph set motif S(6) (Arshad, Khan, Akkurt et al., 2009) to stabilize the molecular conformation (Fig. 1 and Table 1).

Experimental

Methyl 2-aminobenzoate (5 mmol) was dissolved in tetrahydrofuran (10 ml) in a round bottom flask (50 ml). The pH of the solution was maintained at 7–8 using Et3N. 4-Toluene sulfonyl chloride (6 mmol) was suspended to the above solution and refluxed until all the 4-toluene sulfonyl chloride was consumed. After removal of the solvent, water (20 ml) was added to the residue. Then the mixture was extracted with CH2Cl2, and the organic layer was dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. Further purification was carried out by recrystallization in ethanol to give a solid (yield 83.7%). Single crystals suitable for X-ray analysis were obtained by diffusion of n-hexane in an ethanol solution.

Refinement

All C-bonded H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H = 0.93 (aromatic) or 0.96 Å (methyl). Amine H atom H1 was found in a difference map, and its position fixed in final cycles. Isotropic displacement parameters for H atoms were calculated as Uiso(H) = 1.5Ueq(carrier C, N) for methyl H atoms and H1, and Uiso(H) = 1.2Ueq(carrier C) for others.

Figures

Fig. 1.
The structure of the title compound with 30% probability ellipsoids. H atoms are shown as spheres of arbitrary radii. The dashed line represents a hydrogen bond.

Crystal data

C15H15NO4SF(000) = 640
Mr = 305.34Dx = 1.360 Mg m3
Monoclinic, P21/cMelting point: 380 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 15.0129 (13) ÅCell parameters from 3425 reflections
b = 8.3593 (7) Åθ = 2.3–27.0°
c = 11.9664 (11) ŵ = 0.23 mm1
β = 96.854 (2)°T = 295 K
V = 1491.0 (2) Å3Block, colourless
Z = 40.24 × 0.16 × 0.14 mm

Data collection

Bruker APEXII area-detector diffractometer2639 independent reflections
Radiation source: fine-focus sealed tube2230 reflections with I > 2σ(I)
graphiteRint = 0.024
[var phi] and ω scansθmax = 25.1°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)h = −16→17
Tmin = 0.947, Tmax = 0.968k = −9→9
7663 measured reflectionsl = −14→9

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0512P)2 + 0.3683P] where P = (Fo2 + 2Fc2)/3
2639 reflections(Δ/σ)max = 0.001
191 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = −0.32 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
S10.78611 (3)0.16418 (5)0.77097 (4)0.04976 (17)
O10.56582 (10)0.0349 (2)0.36179 (12)0.0866 (5)
O20.61287 (10)0.2115 (2)0.49515 (14)0.0784 (4)
O30.80078 (9)0.05619 (17)0.86305 (10)0.0642 (4)
O40.76453 (10)0.32689 (16)0.79146 (12)0.0677 (4)
N10.70193 (9)0.10160 (18)0.68303 (13)0.0536 (4)
H10.67980.17620.63670.082 (7)*
C10.52814 (17)0.1643 (4)0.2920 (2)0.1100 (11)
H1A0.47630.20570.32210.165*
H1B0.51110.12580.21690.165*
H1C0.57200.24770.29060.165*
C20.60786 (12)0.0751 (3)0.46213 (17)0.0623 (5)
C30.64536 (11)−0.0668 (2)0.52490 (15)0.0524 (4)
C40.69256 (10)−0.0513 (2)0.63324 (14)0.0474 (4)
C50.72532 (13)−0.1874 (2)0.68995 (18)0.0604 (5)
H50.7568−0.17810.76150.072*
C60.71195 (15)−0.3359 (2)0.6419 (2)0.0748 (6)
H60.7343−0.42610.68120.090*
C70.66594 (16)−0.3525 (3)0.5364 (2)0.0810 (7)
H70.6571−0.45340.50420.097*
C80.63345 (15)−0.2203 (3)0.47946 (19)0.0716 (6)
H80.6023−0.23240.40800.086*
C90.88094 (11)0.16066 (19)0.69848 (13)0.0436 (4)
C100.88227 (13)0.2541 (2)0.60377 (15)0.0556 (5)
H100.83230.31460.57660.067*
C110.95774 (14)0.2569 (3)0.55021 (16)0.0626 (5)
H110.95850.32010.48640.075*
C121.03322 (12)0.1678 (2)0.58876 (16)0.0581 (5)
C131.03009 (13)0.0749 (2)0.68292 (17)0.0623 (5)
H131.08000.01440.71010.075*
C140.95457 (12)0.0694 (2)0.73804 (15)0.0541 (4)
H140.95330.00480.80110.065*
C151.11567 (15)0.1736 (3)0.5291 (2)0.0877 (8)
H15A1.14550.27440.54380.132*
H15B1.09880.16200.44950.132*
H15C1.15550.08830.55570.132*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0530 (3)0.0496 (3)0.0468 (3)−0.00029 (19)0.00665 (19)−0.00452 (18)
O10.0675 (9)0.1255 (14)0.0618 (9)−0.0107 (9)−0.0128 (7)0.0207 (9)
O20.0743 (10)0.0717 (10)0.0861 (11)0.0118 (8)−0.0036 (8)0.0221 (9)
O30.0755 (9)0.0734 (9)0.0435 (7)−0.0095 (7)0.0067 (6)0.0063 (6)
O40.0695 (9)0.0557 (8)0.0801 (9)0.0029 (6)0.0177 (7)−0.0180 (7)
N10.0498 (8)0.0470 (8)0.0620 (9)0.0048 (7)−0.0016 (7)−0.0006 (7)
C10.0695 (15)0.170 (3)0.0853 (17)−0.0053 (16)−0.0123 (13)0.0621 (19)
C20.0391 (9)0.0881 (16)0.0591 (12)−0.0040 (10)0.0037 (8)0.0139 (11)
C30.0395 (9)0.0634 (11)0.0542 (10)−0.0029 (8)0.0053 (7)0.0010 (9)
C40.0382 (8)0.0497 (10)0.0549 (10)0.0001 (7)0.0078 (7)−0.0011 (8)
C50.0592 (11)0.0540 (11)0.0657 (12)0.0030 (9)−0.0018 (9)0.0046 (9)
C60.0740 (14)0.0486 (12)0.1004 (17)0.0041 (10)0.0046 (13)0.0025 (11)
C70.0807 (15)0.0570 (13)0.1052 (19)−0.0042 (11)0.0099 (14)−0.0210 (13)
C80.0667 (13)0.0823 (15)0.0642 (13)−0.0117 (11)0.0007 (10)−0.0163 (11)
C90.0478 (9)0.0432 (9)0.0384 (8)0.0004 (7)−0.0004 (7)−0.0031 (7)
C100.0557 (11)0.0626 (12)0.0470 (10)0.0063 (9)0.0004 (8)0.0076 (8)
C110.0692 (13)0.0724 (14)0.0463 (10)−0.0107 (10)0.0077 (9)0.0042 (9)
C120.0525 (11)0.0652 (12)0.0572 (11)−0.0128 (9)0.0091 (9)−0.0235 (9)
C130.0495 (11)0.0650 (12)0.0705 (13)0.0103 (9)−0.0010 (9)−0.0100 (10)
C140.0588 (11)0.0532 (11)0.0484 (10)0.0087 (8)−0.0013 (8)0.0033 (8)
C150.0654 (14)0.109 (2)0.0933 (17)−0.0258 (13)0.0296 (12)−0.0401 (15)

Geometric parameters (Å, °)

S1—O31.4212 (13)C6—H60.9300
S1—O41.4262 (14)C7—C81.358 (3)
S1—N11.6311 (15)C7—H70.9300
S1—C91.7535 (17)C8—H80.9300
O1—C21.331 (2)C9—C101.379 (2)
O1—C11.440 (3)C9—C141.380 (2)
O2—C21.206 (3)C10—C111.367 (3)
N1—C41.410 (2)C10—H100.9300
N1—H10.8734C11—C121.388 (3)
C1—H1A0.9600C11—H110.9300
C1—H1B0.9600C12—C131.374 (3)
C1—H1C0.9600C12—C151.502 (3)
C2—C31.479 (3)C13—C141.379 (3)
C3—C81.397 (3)C13—H130.9300
C3—C41.407 (2)C14—H140.9300
C4—C51.385 (2)C15—H15A0.9600
C5—C61.373 (3)C15—H15B0.9600
C5—H50.9300C15—H15C0.9600
C6—C71.372 (3)
O3—S1—O4119.33 (9)C8—C7—C6119.4 (2)
O3—S1—N1109.45 (8)C8—C7—H7120.3
O4—S1—N1104.03 (8)C6—C7—H7120.3
O3—S1—C9108.24 (8)C7—C8—C3122.0 (2)
O4—S1—C9108.40 (8)C7—C8—H8119.0
N1—S1—C9106.73 (8)C3—C8—H8119.0
C2—O1—C1116.4 (2)C10—C9—C14120.39 (17)
C4—N1—S1126.43 (12)C10—C9—S1119.30 (13)
C4—N1—H1111.6C14—C9—S1120.27 (13)
S1—N1—H1112.8C11—C10—C9119.29 (17)
O1—C1—H1A109.5C11—C10—H10120.4
O1—C1—H1B109.5C9—C10—H10120.4
H1A—C1—H1B109.5C10—C11—C12121.63 (18)
O1—C1—H1C109.5C10—C11—H11119.2
H1A—C1—H1C109.5C12—C11—H11119.2
H1B—C1—H1C109.5C13—C12—C11117.99 (17)
O2—C2—O1122.6 (2)C13—C12—C15121.3 (2)
O2—C2—C3125.93 (19)C11—C12—C15120.7 (2)
O1—C2—C3111.5 (2)C12—C13—C14121.46 (18)
C8—C3—C4118.07 (18)C12—C13—H13119.3
C8—C3—C2121.06 (18)C14—C13—H13119.3
C4—C3—C2120.86 (17)C13—C14—C9119.23 (17)
C5—C4—C3119.06 (17)C13—C14—H14120.4
C5—C4—N1121.75 (16)C9—C14—H14120.4
C3—C4—N1119.14 (16)C12—C15—H15A109.5
C6—C5—C4120.82 (19)C12—C15—H15B109.5
C6—C5—H5119.6H15A—C15—H15B109.5
C4—C5—H5119.6C12—C15—H15C109.5
C7—C6—C5120.6 (2)H15A—C15—H15C109.5
C7—C6—H6119.7H15B—C15—H15C109.5
C5—C6—H6119.7
O3—S1—N1—C4−53.87 (17)C6—C7—C8—C30.0 (4)
O4—S1—N1—C4177.55 (15)C4—C3—C8—C7−0.1 (3)
C9—S1—N1—C463.05 (16)C2—C3—C8—C7−178.8 (2)
C1—O1—C2—O21.7 (3)O3—S1—C9—C10178.84 (13)
C1—O1—C2—C3−178.72 (17)O4—S1—C9—C10−50.38 (16)
O2—C2—C3—C8178.3 (2)N1—S1—C9—C1061.13 (15)
O1—C2—C3—C8−1.3 (2)O3—S1—C9—C14−3.30 (16)
O2—C2—C3—C4−0.4 (3)O4—S1—C9—C14127.47 (15)
O1—C2—C3—C4−179.97 (15)N1—S1—C9—C14−121.02 (14)
C8—C3—C4—C50.2 (3)C14—C9—C10—C11−0.8 (3)
C2—C3—C4—C5178.93 (16)S1—C9—C10—C11177.06 (14)
C8—C3—C4—N1−177.13 (16)C9—C10—C11—C120.1 (3)
C2—C3—C4—N11.6 (2)C10—C11—C12—C130.3 (3)
S1—N1—C4—C534.0 (2)C10—C11—C12—C15−179.53 (18)
S1—N1—C4—C3−148.77 (14)C11—C12—C13—C140.1 (3)
C3—C4—C5—C6−0.2 (3)C15—C12—C13—C14179.90 (18)
N1—C4—C5—C6177.03 (18)C12—C13—C14—C9−0.8 (3)
C4—C5—C6—C70.1 (3)C10—C9—C14—C131.2 (3)
C5—C6—C7—C80.0 (4)S1—C9—C14—C13−176.68 (14)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O20.871.892.640 (2)143

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2263).

References

  • Arshad, M. N., Khan, I. U., Akkurt, M., Shafiq, M. & Mustafa, G. (2009). Acta Cryst. E65, o1610–o1611. [PMC free article] [PubMed]
  • Arshad, M. N., Khan, I. U., Shafiq, M. & Mukhtar, A. (2009). Acta Cryst. E65, o549. [PMC free article] [PubMed]
  • Bruker (2005). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Krishnaiah, M., Narayana Raju, K. V., Lu, I.-L., Chen, Y.-S. & Narasinga Rao, S. (1995). Acta Cryst. C51, 2429–2430.
  • Schultz, T. W., Sinks, G. D. & Miller, L. A. (2001). Environ. Toxicol.16, 543–549. [PubMed]
  • Sheldrick, G. M. (2003). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Sheppard, G. S. et al. (2006). J. Med. Chem.49, 3832–3849. [PubMed]
  • Xiong, J., Cai, X.-Q., Yin, P. & Hu, M.-L. (2007). Acta Phys. Chim. Sin.23, 1183–1188.

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