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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 4| April 2012| Pages o1009-o1010

N-(2-Formyl­phen­yl)-4-toluene­sulfonamide: a second monoclinic polymorph

aDepartment of Physics, Thanthai Periyar Government Institute of Technology, Vellore 632 002, India, bDepartment of Physics, Bharathidasan Engineering College, Nattrampalli, Vellore 635 854, India, and cDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India
*Correspondence e-mail: smurugavel27@gmail.com

(Received 20 February 2012; accepted 2 March 2012; online 10 March 2012)

The title compound, C14H13NO3S, (I), is a second monoclinic polymorph. The original polymorph, (II), was reported by Mahía et al. [Acta Cryst. (1999), C55, 2158–2160]. Polymorph (II) crystalllized in the space group P21/c (Z = 4), whereas the title polymorph (I) occurs in the space group P21/n (Z = 4). The dihedral angle between the two aromatic rings is 75.9 (1)° in (I) compared to 81.9 (1)° for (II). In both polymorphs, two S(6) rings are generated by intra­molecular N—H⋯O and C—H⋯O hydrogen bonds, resulting in similar mol­ecular geometries. However, the two polymorphs differ concerning their crystal packing. In (I), mol­ecules are linked into C(8) zigzag chains along the b axis by C—H⋯O hydrogen bonds, whereas in (II) mol­ecules are linked by C—H⋯O hydrogen bonds, forming C(7) chains along the b axis. The title polymorph is further stabilized by inter­molecular C—H⋯π and ππ inter­actions [centroid–centroid distance = 3.814 (1) Å]. These inter­actions are not evident in polymorph (II).

Related literature

For biological applications of sulfonamides, see: Connor (1998[Connor, E. E. (1998). Prim. Care Update Ob. Gyn. 5, 32-35.]); Berredjem et al. (2000[Berredjem, M., Regainia, Z., Djahoudi, A., Aouf, N.-E., Dewynter, G. & Montero, J.-L. (2000). Phosphorus Sulfur Silicon Relat. Elem. 165, 249-264.]); Lee & Lee (2002[Lee, J. S. & Lee, C. H. (2002). Bull. Korean Chem. Soc. 23, 167-169.]); Xiao & Timberlake (2000[Xiao, Z. & Timberlake, J. W. (2000). J. Heterocycl. Chem. 37, 773-777.]). For the first monoclinic polymorph, see: Mahía et al. (1999[Mahía, J., Maestro, M., Vázquez, M., Bermejo, M. R., González, A. M. & Maneiro, M. (1999). Acta Cryst. C55, 2158-2160.]). For a related structure, see: Zhang et al. (2010[Zhang, G.-Y., Chen, D.-J., Guo, X.-Y., Wang, S.-H. & Chang, J.-G. (2010). Acta Cryst. E66, o346.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C14H13NO3S

  • Mr = 275.31

  • Monoclinic, P 21 /n

  • a = 11.5409 (4) Å

  • b = 8.1345 (2) Å

  • c = 14.1115 (5) Å

  • β = 97.294 (2)°

  • V = 1314.06 (7) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.25 mm−1

  • T = 293 K

  • 0.25 × 0.23 × 0.18 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.940, Tmax = 0.956

  • 16047 measured reflections

  • 4254 independent reflections

  • 2678 reflections with I > 2σ(I)

  • Rint = 0.029

Refinement
  • R[F2 > 2σ(F2)] = 0.049

  • wR(F2) = 0.155

  • S = 1.02

  • 4254 reflections

  • 174 parameters

  • H-atom parameters constrained

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.40 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C8–C13 benzene ring.

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O1 0.86 1.94 2.655 (2) 140
C2—H2⋯O2 0.93 2.48 3.059 (2) 120
C14—H14C⋯O3i 0.96 2.52 3.439 (3) 161
C5—H5⋯Cg1ii 0.93 2.82 3.658 (2) 150
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Sulfonamides are an important category of pharmaceutical compounds with a broad spectrum of biological activities such as herbicidal, anti-malarial, anti-convulsant and anti-hypertensive (Connor, 1998; Xiao & Timberlake, 2000; Berredjem et al., 2000; Lee & Lee, 2002). In this work we report the crystal structure of the title compound (Fig 1, Alternative name: 2–tosylaminobenzaldehyde), which is the second monoclinic polymorph reported.

The original polymorph (compound (II)) was previously reported by Mahía et al. (1999) and was shown to crystallize in the monoclinic space group P21/c, with a = 13.899 (7), b = 8.237 (4), c = 12.063 (6) Å, β = 105.899 (1)° and Z = 4. In the present work, the title compound crystallized in the space group P21/n with a = 11.5409 (4), b = 8.1345 (2), c = 14.1115 (5) Å, β = 97.294 (2)° and Z = 4. The dihedral angle between the two aromatic rings is 75.9 (1)° in (I) compared to 81.9 (1)° for (II). The bond distances in the molecule are normal and comparable to those in the previously published polymorph and in a closely related sulfonamide derivative (Zhang et al., 2010).

In both polymorphs, the molecular packing is stabilized by intramolecular N1—H1···O1 and C2—H2···O2 hydrogen bonds, generating two S(6) rings (Bernstein et al., 1995) (Table 1). However, the two polymorphs differ concerning their crystal packing. In compound (II) molecules are linked to form C(7) chains along the b axis by intermolecular C3—H3···O3 hydrogen bonds whereas in the title compound (I), molecules are linked by intermolecular C14—H14C···O3 hydrogen bonds to form C(8) zigzag chains along the b axis (Fig. 2). The crystal packing (Fig. 3) is further stabilized by C—H···π interactions between a formylphenyl H atom and the benzene ring (C8–C13) of a neighbouring molecule, with a C5—H5···Cg1ii distance of 3.658 (2) Å (Table 1; Cg1 is the centroid of the C8–C13 benzene ring, Symmetry code: ii = 1 - x, 1 - y, -z). Additional stability arises from aromatic ππ interaction between the benzene rings of neighbouring molecules, with Cg2—Cg2ii distance of 3.814 (1) Å (Fig. 3; Cg2 is the centroid of the C1—C6 benzene ring, Symmetry code: ii = 1 - x, 1 - y, -z). The C—H···π and ππ interactions are not evident in compound (II).

Related literature top

For biological applications of sulfonamides, see: Connor (1998); Berredjem et al. (2000); Lee & Lee (2002); Xiao & Timberlake (2000). For the first monoclinic polymorph, see: Mahía et al. (1999). For a related structure, see: Zhang et al. (2010). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

To a stirred solution of (2-aminophenyl)methanol in chloroform, 1.5 equiv of pyridine and 1.5 equiv of 4-methylbenzene-1-sulfonyl chloride were added at room temperature over a period of 18 h. The resulting brown colored solution was quenched with aqueous HCl. After workup a pale brownish solid was obtained. The combined organic fractions were dried over Na2SO4 and partially concentrated under reduced pressure at 25°C. The product was precipitated with diethylether. Further, MnO2 was added to a solution of 2-tosylaminobenzyl alcohol in dry 1,2-dichloroethane solvent under nitrogen atmosphere. The suspension was stirred at 80°C in reflux condition for 5 h and filtered through Celite. The filtrate was partially concentrated on a rotatory evaporator at 25°C and the product was precipitated with diethylether. Recystallization of the product from CH2Cl2 yielded pale yellow crystals of the title compound (Yield: 86%). Crystals of the original polymorph were prepared by evaporation of CHCl3 from a solution of the title compound at room temperature (Mahía et al., 1999).

Refinement top

H atoms were positioned geometrically (N–H = 0.86 Å and C–H = 0.93–0.96 Å and allowed to ride on their parent atoms, with Uiso(H) =1.5Ueq for methyl H atoms and 1.2Ueq(C) for other H atoms.

Structure description top

Sulfonamides are an important category of pharmaceutical compounds with a broad spectrum of biological activities such as herbicidal, anti-malarial, anti-convulsant and anti-hypertensive (Connor, 1998; Xiao & Timberlake, 2000; Berredjem et al., 2000; Lee & Lee, 2002). In this work we report the crystal structure of the title compound (Fig 1, Alternative name: 2–tosylaminobenzaldehyde), which is the second monoclinic polymorph reported.

The original polymorph (compound (II)) was previously reported by Mahía et al. (1999) and was shown to crystallize in the monoclinic space group P21/c, with a = 13.899 (7), b = 8.237 (4), c = 12.063 (6) Å, β = 105.899 (1)° and Z = 4. In the present work, the title compound crystallized in the space group P21/n with a = 11.5409 (4), b = 8.1345 (2), c = 14.1115 (5) Å, β = 97.294 (2)° and Z = 4. The dihedral angle between the two aromatic rings is 75.9 (1)° in (I) compared to 81.9 (1)° for (II). The bond distances in the molecule are normal and comparable to those in the previously published polymorph and in a closely related sulfonamide derivative (Zhang et al., 2010).

In both polymorphs, the molecular packing is stabilized by intramolecular N1—H1···O1 and C2—H2···O2 hydrogen bonds, generating two S(6) rings (Bernstein et al., 1995) (Table 1). However, the two polymorphs differ concerning their crystal packing. In compound (II) molecules are linked to form C(7) chains along the b axis by intermolecular C3—H3···O3 hydrogen bonds whereas in the title compound (I), molecules are linked by intermolecular C14—H14C···O3 hydrogen bonds to form C(8) zigzag chains along the b axis (Fig. 2). The crystal packing (Fig. 3) is further stabilized by C—H···π interactions between a formylphenyl H atom and the benzene ring (C8–C13) of a neighbouring molecule, with a C5—H5···Cg1ii distance of 3.658 (2) Å (Table 1; Cg1 is the centroid of the C8–C13 benzene ring, Symmetry code: ii = 1 - x, 1 - y, -z). Additional stability arises from aromatic ππ interaction between the benzene rings of neighbouring molecules, with Cg2—Cg2ii distance of 3.814 (1) Å (Fig. 3; Cg2 is the centroid of the C1—C6 benzene ring, Symmetry code: ii = 1 - x, 1 - y, -z). The C—H···π and ππ interactions are not evident in compound (II).

For biological applications of sulfonamides, see: Connor (1998); Berredjem et al. (2000); Lee & Lee (2002); Xiao & Timberlake (2000). For the first monoclinic polymorph, see: Mahía et al. (1999). For a related structure, see: Zhang et al. (2010). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level. H atoms are presented as a small spheres of arbitrary radius.
[Figure 2] Fig. 2. Part of the crystal structure of (I) showing C—H···O hydrogen bonds (blue dotted lines), with the formation of C(8) chains along the b axis. [Symmetry codes: (i) x, 1 + y, z; (iii) x, 2 + y, z].
[Figure 3] Fig. 3. A view of the C—H···π and ππ interactions (dotted lines) in the crystal structure of the title compound. Cg1 and Cg2 denotes centroids of the C8–C13 benzene ring and C1–C6 benzene ring, respectively. [Symmetry code: (ii) 1 - x, 1 - y, -z].
N-(2-Formylphenyl)-p–toluenesulfonamide top
Crystal data top
C14H13NO3SF(000) = 576
Mr = 275.31Dx = 1.392 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4561 reflections
a = 11.5409 (4) Åθ = 2.2–32.0°
b = 8.1345 (2) ŵ = 0.25 mm1
c = 14.1115 (5) ÅT = 293 K
β = 97.294 (2)°Block, pale yellow
V = 1314.06 (7) Å30.25 × 0.23 × 0.18 mm
Z = 4
Data collection top
Bruker APEXII CCD
diffractometer
4254 independent reflections
Radiation source: fine-focus sealed tube2678 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
Detector resolution: 10.0 pixels mm-1θmax = 32.0°, θmin = 2.2°
ω scansh = 1516
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1112
Tmin = 0.940, Tmax = 0.956l = 1621
16047 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H-atom parameters constrained
wR(F2) = 0.155 w = 1/[σ2(Fo2) + (0.0735P)2 + 0.2545P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
4254 reflectionsΔρmax = 0.30 e Å3
174 parametersΔρmin = 0.40 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.023 (3)
Crystal data top
C14H13NO3SV = 1314.06 (7) Å3
Mr = 275.31Z = 4
Monoclinic, P21/nMo Kα radiation
a = 11.5409 (4) ŵ = 0.25 mm1
b = 8.1345 (2) ÅT = 293 K
c = 14.1115 (5) Å0.25 × 0.23 × 0.18 mm
β = 97.294 (2)°
Data collection top
Bruker APEXII CCD
diffractometer
4254 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2678 reflections with I > 2σ(I)
Tmin = 0.940, Tmax = 0.956Rint = 0.029
16047 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.155H-atom parameters constrained
S = 1.02Δρmax = 0.30 e Å3
4254 reflectionsΔρmin = 0.40 e Å3
174 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
S10.52951 (5)0.12891 (6)0.23059 (3)0.06087 (19)
C10.56496 (14)0.25944 (19)0.05828 (10)0.0454 (4)
C60.51658 (14)0.27675 (19)0.03793 (11)0.0472 (4)
N10.50096 (14)0.1677 (2)0.11710 (10)0.0566 (4)
H10.43720.12560.08920.068*
C50.57925 (17)0.3623 (2)0.10019 (12)0.0580 (4)
H50.54840.37210.16410.070*
O10.33743 (12)0.13376 (18)0.03182 (11)0.0708 (4)
C80.49992 (15)0.3098 (2)0.29018 (11)0.0497 (4)
C130.58899 (15)0.4156 (2)0.32385 (12)0.0563 (4)
H130.66570.39160.31510.068*
C70.40286 (17)0.2107 (2)0.07598 (13)0.0608 (5)
H70.37800.22930.14040.073*
C20.67100 (15)0.3343 (2)0.08926 (12)0.0556 (4)
H20.70260.32730.15310.067*
O20.65042 (14)0.0934 (2)0.25269 (11)0.0804 (5)
C110.45109 (18)0.5950 (2)0.38535 (13)0.0614 (5)
C120.56359 (17)0.5566 (3)0.37043 (14)0.0627 (5)
H120.62390.62810.39250.075*
C40.68487 (18)0.4321 (3)0.06949 (15)0.0640 (5)
H40.72620.48770.11200.077*
C100.36292 (18)0.4862 (3)0.35138 (15)0.0680 (5)
H100.28640.50980.36080.082*
O30.44396 (17)0.0087 (2)0.24676 (12)0.0891 (5)
C30.72931 (17)0.4190 (2)0.02550 (15)0.0612 (5)
H30.80040.46860.04700.073*
C90.38592 (17)0.3451 (3)0.30435 (14)0.0626 (5)
H90.32570.27360.28210.075*
C140.4263 (3)0.7500 (3)0.43715 (17)0.0867 (7)
H14A0.48740.76850.48880.130*
H14B0.35300.73940.46200.130*
H14C0.42260.84120.39370.130*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0805 (4)0.0561 (3)0.0451 (2)0.0081 (2)0.0047 (2)0.00904 (18)
C10.0500 (9)0.0445 (8)0.0410 (7)0.0082 (7)0.0029 (6)0.0031 (6)
C60.0532 (9)0.0437 (8)0.0427 (8)0.0071 (7)0.0011 (6)0.0044 (6)
N10.0595 (9)0.0669 (9)0.0423 (7)0.0054 (7)0.0017 (6)0.0015 (6)
C50.0707 (12)0.0595 (10)0.0421 (8)0.0054 (8)0.0008 (8)0.0025 (7)
O10.0607 (8)0.0794 (10)0.0696 (9)0.0118 (7)0.0021 (7)0.0111 (7)
C80.0514 (9)0.0599 (9)0.0378 (7)0.0042 (7)0.0054 (6)0.0084 (7)
C130.0441 (9)0.0767 (12)0.0476 (9)0.0044 (8)0.0039 (7)0.0005 (8)
C70.0642 (12)0.0651 (11)0.0489 (9)0.0029 (9)0.0086 (8)0.0085 (8)
C20.0519 (10)0.0678 (11)0.0445 (8)0.0046 (8)0.0039 (7)0.0020 (7)
O20.0930 (11)0.0843 (10)0.0605 (8)0.0407 (8)0.0041 (7)0.0065 (7)
C110.0777 (13)0.0623 (11)0.0476 (9)0.0109 (9)0.0218 (9)0.0132 (8)
C120.0633 (11)0.0707 (12)0.0548 (10)0.0064 (9)0.0098 (8)0.0037 (9)
C40.0695 (12)0.0635 (11)0.0608 (11)0.0013 (9)0.0150 (9)0.0072 (9)
C100.0535 (11)0.0891 (15)0.0649 (12)0.0125 (10)0.0210 (9)0.0108 (10)
O30.1354 (14)0.0640 (9)0.0700 (10)0.0193 (9)0.0206 (9)0.0124 (7)
C30.0514 (10)0.0642 (11)0.0672 (12)0.0025 (8)0.0043 (8)0.0027 (9)
C90.0498 (10)0.0785 (13)0.0606 (11)0.0063 (9)0.0115 (8)0.0067 (9)
C140.128 (2)0.0684 (13)0.0712 (14)0.0182 (14)0.0426 (14)0.0085 (11)
Geometric parameters (Å, º) top
S1—O21.4204 (16)C7—H70.9300
S1—O31.4285 (16)C2—C31.375 (3)
S1—N11.6245 (14)C2—H20.9300
S1—C81.7500 (18)C11—C121.377 (3)
C1—C21.387 (2)C11—C101.387 (3)
C1—N11.395 (2)C11—C141.503 (3)
C1—C61.408 (2)C12—H120.9300
C6—C51.393 (2)C4—C31.377 (3)
C6—C71.456 (3)C4—H40.9300
N1—H10.8600C10—C91.369 (3)
C5—C41.364 (3)C10—H100.9300
C5—H50.9300C3—H30.9300
O1—C71.212 (2)C9—H90.9300
C8—C131.378 (3)C14—H14A0.9600
C8—C91.386 (3)C14—H14B0.9600
C13—C121.372 (3)C14—H14C0.9600
C13—H130.9300
O2—S1—O3120.36 (11)C3—C2—C1119.95 (16)
O2—S1—N1109.05 (9)C3—C2—H2120.0
O3—S1—N1103.45 (9)C1—C2—H2120.0
O2—S1—C8108.16 (9)C12—C11—C10117.85 (19)
O3—S1—C8108.55 (9)C12—C11—C14120.4 (2)
N1—S1—C8106.44 (8)C10—C11—C14121.76 (19)
C2—C1—N1124.04 (14)C13—C12—C11121.71 (19)
C2—C1—C6119.08 (15)C13—C12—H12119.1
N1—C1—C6116.87 (15)C11—C12—H12119.1
C5—C6—C1118.94 (15)C5—C4—C3118.96 (18)
C5—C6—C7117.88 (15)C5—C4—H4120.5
C1—C6—C7123.17 (16)C3—C4—H4120.5
C1—N1—S1129.33 (12)C9—C10—C11121.57 (18)
C1—N1—H1115.3C9—C10—H10119.2
S1—N1—H1115.3C11—C10—H10119.2
C4—C5—C6121.47 (16)C2—C3—C4121.53 (18)
C4—C5—H5119.3C2—C3—H3119.2
C6—C5—H5119.3C4—C3—H3119.2
C13—C8—C9120.11 (18)C10—C9—C8119.3 (2)
C13—C8—S1120.54 (13)C10—C9—H9120.3
C9—C8—S1119.35 (15)C8—C9—H9120.3
C12—C13—C8119.45 (17)C11—C14—H14A109.5
C12—C13—H13120.3C11—C14—H14B109.5
C8—C13—H13120.3H14A—C14—H14B109.5
O1—C7—C6126.30 (17)C11—C14—H14C109.5
O1—C7—H7116.9H14A—C14—H14C109.5
C6—C7—H7116.9H14B—C14—H14C109.5
C2—C1—C6—C52.9 (2)C9—C8—C13—C120.8 (3)
N1—C1—C6—C5177.73 (15)S1—C8—C13—C12179.94 (14)
C2—C1—C6—C7176.46 (16)C5—C6—C7—O1179.95 (18)
N1—C1—C6—C72.9 (2)C1—C6—C7—O10.6 (3)
C2—C1—N1—S11.3 (3)N1—C1—C2—C3178.36 (16)
C6—C1—N1—S1178.02 (13)C6—C1—C2—C32.3 (3)
O2—S1—N1—C141.57 (18)C8—C13—C12—C110.6 (3)
O3—S1—N1—C1170.79 (16)C10—C11—C12—C130.2 (3)
C8—S1—N1—C174.91 (17)C14—C11—C12—C13179.64 (18)
C1—C6—C5—C41.3 (3)C6—C5—C4—C30.9 (3)
C7—C6—C5—C4178.06 (17)C12—C11—C10—C90.1 (3)
O2—S1—C8—C1318.43 (17)C14—C11—C10—C9179.92 (19)
O3—S1—C8—C13150.58 (15)C1—C2—C3—C40.1 (3)
N1—S1—C8—C1398.64 (15)C5—C4—C3—C21.5 (3)
O2—S1—C8—C9160.77 (14)C11—C10—C9—C80.1 (3)
O3—S1—C8—C928.61 (16)C13—C8—C9—C100.5 (3)
N1—S1—C8—C982.16 (15)S1—C8—C9—C10179.68 (15)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C8–C13 benzene ring.
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.861.942.655 (2)140
C2—H2···O20.932.483.059 (2)120
C14—H14C···O3i0.962.523.439 (3)161
C5—H5···Cg1ii0.932.823.658 (2)150
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1, z.

Experimental details

Crystal data
Chemical formulaC14H13NO3S
Mr275.31
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)11.5409 (4), 8.1345 (2), 14.1115 (5)
β (°) 97.294 (2)
V3)1314.06 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.25
Crystal size (mm)0.25 × 0.23 × 0.18
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.940, 0.956
No. of measured, independent and
observed [I > 2σ(I)] reflections
16047, 4254, 2678
Rint0.029
(sin θ/λ)max1)0.746
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.155, 1.02
No. of reflections4254
No. of parameters174
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.30, 0.40

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C8–C13 benzene ring.
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.861.942.655 (2)140.0
C2—H2···O20.932.483.059 (2)120.0
C14—H14C···O3i0.962.523.439 (3)160.5
C5—H5···Cg1ii0.932.823.658 (2)150.0
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1, z.
 

Footnotes

Additional correspondence author, e-mail: bhakthadoss@yahoo.com.

Acknowledgements

The authors thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for his help with the data collection.

References

First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science Google Scholar
First citationBerredjem, M., Regainia, Z., Djahoudi, A., Aouf, N.-E., Dewynter, G. & Montero, J.-L. (2000). Phosphorus Sulfur Silicon Relat. Elem. 165, 249–264.  Web of Science CrossRef CAS Google Scholar
First citationBruker (2004). APEX2, SAINT and XPREP. 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 citationLee, J. S. & Lee, C. H. (2002). Bull. Korean Chem. Soc. 23, 167–169.  Web of Science CrossRef CAS Google Scholar
First citationMahía, J., Maestro, M., Vázquez, M., Bermejo, M. R., González, A. M. & Maneiro, M. (1999). Acta Cryst. C55, 2158–2160.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationXiao, Z. & Timberlake, J. W. (2000). J. Heterocycl. Chem. 37, 773–777.  CrossRef CAS Google Scholar
First citationZhang, G.-Y., Chen, D.-J., Guo, X.-Y., Wang, S.-H. & Chang, J.-G. (2010). Acta Cryst. E66, o346.  Web of Science CSD CrossRef IUCr Journals 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
Volume 68| Part 4| April 2012| Pages o1009-o1010
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds