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

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COMMUNICATIONS
ISSN: 2056-9890

3-(1H-Indol-3-yl)-2-(2-nitro­benzene­sulfonamido)­propanoic acid including an unknown solvate

aMaterials Chemistry laboratory, Department of Chemistry, GC University, Lahore 54000, Pakistan, and bDepartment of Chemistry, University of Aberdeen, Aberdeen AB24 3UE, Scotland
*Correspondence e-mail: iuklodhi@yahoo.com

(Received 19 March 2012; accepted 22 May 2012; online 13 June 2012)

In the title compound, C17H15N3O6S, which crystallized with highly disordered methanol and/or water solvent mol­ecules, the dihedral angle between the the indole and benzene ring systems is 5.3 (2)°, which allows for the formation of intra­molecular ππ stacking inter­actions [centroid–centroid separations = 3.641 (3) and 3.694 (3) Å] and an approximate overall U-shape for the mol­ecule. In the crystal, dimers linked by pairs of Ns—H⋯Oc (s = sulfonamide and c = carboxyl­ate) hydrogen bonds generate R22(10) loops, whereas Ni—H⋯π (i = indole) inter­actions lead to chains propagating in [100] or [010]. Together, these lead to a three-dimensional network in which the solvent voids are present as inter­secting (two-dimensional) systems of [100] and [010] channels. The title compound was found to contain a heavily disordered solvent mol­ecule, which could be methanol or water or a mixture of the two. Due to its uncertain nature and the unresolvable disorder, the data were processed with the SQUEEZE option in PLATON [Spek (2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]). Acta Cryst. D65, 148–155], which revealed 877.8 Å3 of solvent-accessible volume per unit cell and 126 electron-units of scattering density or 109.7 Å3 (16 electron units) per organic mol­ecule.. This was not included in the calculations of overall formula weight, density and absorption coefficient.

Related literature

For related structures and background references to the biological activity of sulfonamides, see: Khan et al. (2011a[Khan, I. U., Arshad, M. N., Mubashar-ur-Rehman, H., Harrison, W. T. A. & Ali, M. B. (2011a). Acta Cryst. E67, o2325.],b[Khan, M. H., Khan, I. U., Arshad, M. N., Rafique, H. M. & Harrison, W. T. A. (2011b). Crystals, 1, 69-77.]). For further synthetic details, see: Deng & Mani (2006[Deng, X. & Mani, N. S. (2006). Green Chem. 8, 835-838.]).

[Scheme 1]

Experimental

Crystal data
  • C17H15N3O6S

  • Mr = 389.38

  • Tetragonal, P 41 21 2

  • a = 9.6818 (5) Å

  • c = 44.017 (3) Å

  • V = 4126.0 (4) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.19 mm−1

  • T = 296 K

  • 0.30 × 0.25 × 0.10 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • 4042 measured reflections

  • 4042 independent reflections

  • 3492 reflections with I > 2σ(I)

Refinement
  • R[F2 > 2σ(F2)] = 0.067

  • wR(F2) = 0.168

  • S = 1.07

  • 4042 reflections

  • 245 parameters

  • H-atom parameters constrained

  • Δρmax = 0.21 e Å−3

  • Δρmin = −0.24 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1581 Friedel pairs

  • Flack parameter: 0.03 (15)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯Cg1i 0.86 2.77 3.565 (4) 155
N2—H2⋯O1ii 0.86 2.10 2.918 (4) 158
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+{\script{3\over 4}}]; (ii) y, x, -z+1.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. 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 (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

As part of our ongoing studies of chiral sulfonamides with possible biological activity (Khan et al., 2011a,b), we now report the structure of the title compound, (I). Compound (I) was found to contain a heavily disordered solvent molecule, which could be methanol or water or a mixture of the two. Due to its uncertain nature and the unresolvable disorder, the data were processed with the SQUEEZE option in PLATON (Spek, 2009), to remove the solvent contribution to the scattering.

The molecular structure of (I) (Fig. 1) approximates to a U-shape, with the indole ring system (C1—C8/N1; r.m.s. deviation = 0.007 Å) and benzene ring (C12–C17) lying approximately parallel to each other [dihedral angle = 5.3 (2)°]. This allows intramolecular aromatic π-π stacking to occur: the separations of the centroid of the C12–C17 benzene ring with those of the C1–C6 and C1/C6/C7/C8/N1 rings are 3.641 (3) Å and 3.694 (3) Å, respectively. The N3/O5/O6 nitro group is twisted out of the plane of its atttached ring by 48.9 (4)°. The configuration of the stereogenic carbon atom (C10) in (I) is S, which is consistent with that of the equivalent atom in the starting material.

In the crystal, the molecules are linked into dimers via pairs of Ns–H···Oc (s = sulfonamide, c = carboxylate) hydrogen bonds (Fig. 2, Table 1), which result in R22(10) loops. A crystallographic twofold axis directed along [110] generates the second molecule from the asymmetric molecule. In addition, weak Ni—H···π (i = indole) interactions occur: these lead to [100] chains for the asymmetric molecule and [010] chains for symmetry-generated molecules in other locations in the unit-cell (Fig. 3). The carboxylic acid O—H group is directed towards the solvent void and probably forms a hydrogen bond to the solvent.

Together, the N–H···O and N–H···π bonds generate a three-dimensional network of molecules within the distinctive "tall" tetragonal unit-cell (Fig. 3). The solvent voids are apparent as square grids of intersecting [100] and [010] pseudo channels lying at z = 0, z = 1/4 and symmetry equivalent locations.

The molcular conformation and crystal structure (Khan et al., 2011a) of the closely related compound 3-(1H-indol-3-yl)-2-(toluene-4-sulfonylamino)-propionic acid monohydrate, (II), are completely different to (I). In (II), where a para-toluene substituent has replaced the 2-nitrobebzene substituent in (I), the organic molecule adopts an extended Z-shaped conformation and no intramolecular π-π stacking can occur. In the crystal of (II), in which the solvent water molecule was located, Ns–H···Os hydrogen bonds and Oc–H···Ow (s = sulfonamide, c = carboxylic acid, w = water) hydrogen bonds generate chains and the crystal symmetry is monoclinic. Another feature of (II) not seen in (I) is the presence of a short intermolecular C—H···O interaction arising from the α (chiral) C atom (Khan et al., 2011b). However, it is interesting to note that (I) and (II) both feature an unusual Ni–H···π (i = indole) interaction.

Related literature top

For related structures and background references to the biological activity of sulfonamides, see: Khan et al. (2011a,b). For further synthetic details, see: Deng & Mani (2006).

Experimental top

The title compound was prepared following the literature method (Deng & Mani, 2006) and recrystalized from methanol by slow evaporation to yield yellow blocks of (I).

Refinement top

Due to the disordered solvent molecule and its uncertain identity, the data were processed with SQUEEZE in PLATON (Spek, 2009). This revealed 877.8 Å3 of solvent accessible volume per unit cell and 126 electron-units of scattering density or 109.7 Å3 (16 electron units) per organic molecule. This was not included in the calculations of overall formula weight, density and absorption coefficient. The original data set consisted of 31099 measured reflections (-11 h 11, -11 k 11, -54 l 54), for which Rint was 0.068.

The C- and N-bound H-atoms were geometrically placed (C—H = 0.93–0.98 Å, N—H = 0.86 Å) and refined as riding with Uiso(H) = 1.2Ueq(carrier). The O-bound H was located in a difference map and refined as riding in its as-found relative position with Uiso(H) = 1.5Ueq(O).

Structure description top

As part of our ongoing studies of chiral sulfonamides with possible biological activity (Khan et al., 2011a,b), we now report the structure of the title compound, (I). Compound (I) was found to contain a heavily disordered solvent molecule, which could be methanol or water or a mixture of the two. Due to its uncertain nature and the unresolvable disorder, the data were processed with the SQUEEZE option in PLATON (Spek, 2009), to remove the solvent contribution to the scattering.

The molecular structure of (I) (Fig. 1) approximates to a U-shape, with the indole ring system (C1—C8/N1; r.m.s. deviation = 0.007 Å) and benzene ring (C12–C17) lying approximately parallel to each other [dihedral angle = 5.3 (2)°]. This allows intramolecular aromatic π-π stacking to occur: the separations of the centroid of the C12–C17 benzene ring with those of the C1–C6 and C1/C6/C7/C8/N1 rings are 3.641 (3) Å and 3.694 (3) Å, respectively. The N3/O5/O6 nitro group is twisted out of the plane of its atttached ring by 48.9 (4)°. The configuration of the stereogenic carbon atom (C10) in (I) is S, which is consistent with that of the equivalent atom in the starting material.

In the crystal, the molecules are linked into dimers via pairs of Ns–H···Oc (s = sulfonamide, c = carboxylate) hydrogen bonds (Fig. 2, Table 1), which result in R22(10) loops. A crystallographic twofold axis directed along [110] generates the second molecule from the asymmetric molecule. In addition, weak Ni—H···π (i = indole) interactions occur: these lead to [100] chains for the asymmetric molecule and [010] chains for symmetry-generated molecules in other locations in the unit-cell (Fig. 3). The carboxylic acid O—H group is directed towards the solvent void and probably forms a hydrogen bond to the solvent.

Together, the N–H···O and N–H···π bonds generate a three-dimensional network of molecules within the distinctive "tall" tetragonal unit-cell (Fig. 3). The solvent voids are apparent as square grids of intersecting [100] and [010] pseudo channels lying at z = 0, z = 1/4 and symmetry equivalent locations.

The molcular conformation and crystal structure (Khan et al., 2011a) of the closely related compound 3-(1H-indol-3-yl)-2-(toluene-4-sulfonylamino)-propionic acid monohydrate, (II), are completely different to (I). In (II), where a para-toluene substituent has replaced the 2-nitrobebzene substituent in (I), the organic molecule adopts an extended Z-shaped conformation and no intramolecular π-π stacking can occur. In the crystal of (II), in which the solvent water molecule was located, Ns–H···Os hydrogen bonds and Oc–H···Ow (s = sulfonamide, c = carboxylic acid, w = water) hydrogen bonds generate chains and the crystal symmetry is monoclinic. Another feature of (II) not seen in (I) is the presence of a short intermolecular C—H···O interaction arising from the α (chiral) C atom (Khan et al., 2011b). However, it is interesting to note that (I) and (II) both feature an unusual Ni–H···π (i = indole) interaction.

For related structures and background references to the biological activity of sulfonamides, see: Khan et al. (2011a,b). For further synthetic details, see: Deng & Mani (2006).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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. The molecular structure of (I) with displacement ellipsoids drawn at the 40% probability level and the intramolecular π-π stacking interactions shown as double-dashed lines betweent the ring centroids.
[Figure 2] Fig. 2. Detail of the structure of (I) showing the formation of dimers linked by pairs of N—H···O hydrogen bonds, thus generating R22(10) loops. All C-bonded H atoms omitted for clarity. Symmetry code: (ii) y, x, 1 - z.
[Figure 3] Fig. 3. Detail of the structure of (I) showing the formation of [100] chains linked by N—H···π interactions. Cg1 (pink circle) is the centroid of the C1–C6 ring. Symmetry code: (i) x - 1/2, 3/2 - y, 3/4 - z.
[Figure 4] Fig. 4. The unit-cell packing for (I) viewed approximately down [010] showing the solvent voids.
3-(1H-Indol-3-yl)-2-(2-nitrobenzenesulfonamido)propanoic acid top
Crystal data top
C17H15N3O6SDx = 1.254 Mg m3
Mr = 389.38Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P41212Cell parameters from 9980 reflections
Hall symbol: P 4abw 2nwθ = 2.8–26.9°
a = 9.6818 (5) ŵ = 0.19 mm1
c = 44.017 (3) ÅT = 296 K
V = 4126.0 (4) Å3Block, yellow
Z = 80.30 × 0.25 × 0.10 mm
F(000) = 1616
Data collection top
Bruker Kappa APEXII CCD
diffractometer
3492 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.000
Graphite monochromatorθmax = 26.0°, θmin = 2.5°
ω scansh = 78
4042 measured reflectionsk = 011
4042 independent reflectionsl = 054
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.067 w = 1/[σ2(Fo2) + (0.0679P)2 + 3.5726P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.168(Δ/σ)max < 0.001
S = 1.07Δρmax = 0.21 e Å3
4042 reflectionsΔρmin = 0.24 e Å3
245 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0083 (12)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 1581 Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.03 (15)
Crystal data top
C17H15N3O6SZ = 8
Mr = 389.38Mo Kα radiation
Tetragonal, P41212µ = 0.19 mm1
a = 9.6818 (5) ÅT = 296 K
c = 44.017 (3) Å0.30 × 0.25 × 0.10 mm
V = 4126.0 (4) Å3
Data collection top
Bruker Kappa APEXII CCD
diffractometer
3492 reflections with I > 2σ(I)
4042 measured reflectionsRint = 0.000
4042 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.067H-atom parameters constrained
wR(F2) = 0.168Δρmax = 0.21 e Å3
S = 1.07Δρmin = 0.24 e Å3
4042 reflectionsAbsolute structure: Flack (1983), 1581 Friedel pairs
245 parametersAbsolute structure parameter: 0.03 (15)
0 restraints
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
C10.5558 (4)0.6025 (4)0.39025 (8)0.0488 (8)
C20.6443 (5)0.5208 (5)0.37363 (10)0.0583 (10)
H2A0.71080.46750.38340.070*
C30.6335 (6)0.5186 (6)0.34215 (11)0.0780 (15)
H3A0.69250.46270.33090.094*
C40.5350 (7)0.5994 (6)0.32731 (10)0.0792 (15)
H40.53060.59770.30620.095*
C50.4460 (6)0.6799 (6)0.34293 (11)0.0763 (14)
H50.37990.73280.33290.092*
C60.4564 (5)0.6813 (4)0.37487 (9)0.0558 (10)
C70.4312 (5)0.7179 (5)0.42414 (10)0.0641 (11)
H70.39530.75110.44230.077*
C80.5374 (4)0.6301 (4)0.42204 (8)0.0505 (9)
C90.6174 (4)0.5663 (4)0.44725 (9)0.0554 (10)
H9A0.60130.61800.46580.067*
H9B0.71520.57170.44260.067*
C100.5775 (4)0.4149 (4)0.45240 (8)0.0500 (9)
H100.59160.36390.43340.060*
C110.6702 (4)0.3540 (4)0.47649 (8)0.0481 (9)
C120.2877 (4)0.3494 (4)0.40872 (8)0.0467 (8)
C130.3606 (5)0.2926 (5)0.38483 (9)0.0612 (11)
H130.43220.23100.38870.073*
C140.3275 (6)0.3271 (6)0.35519 (9)0.0734 (14)
H140.37820.29050.33910.088*
C150.2204 (7)0.4150 (6)0.34959 (10)0.0777 (14)
H150.19900.43780.32960.093*
C160.1439 (5)0.4701 (6)0.37262 (11)0.0718 (13)
H160.06960.52810.36860.086*
C170.1800 (4)0.4373 (4)0.40226 (9)0.0552 (10)
S10.33465 (11)0.29054 (11)0.44601 (2)0.0528 (3)
N10.3822 (4)0.7526 (4)0.39580 (9)0.0713 (11)
H10.31620.80940.39200.086*
N20.4319 (3)0.4032 (3)0.46119 (6)0.0484 (7)
H20.39880.45790.47470.058*
N30.0981 (4)0.5018 (4)0.42620 (10)0.0664 (10)
O10.6449 (3)0.3541 (4)0.50311 (6)0.0781 (10)
O20.7836 (3)0.3064 (4)0.46516 (6)0.0853 (12)
H30.84810.27660.47970.102*
O30.4148 (3)0.1700 (3)0.44107 (7)0.0718 (9)
O40.2103 (3)0.2828 (4)0.46327 (7)0.0755 (10)
O50.1554 (4)0.5580 (5)0.44684 (9)0.0921 (12)
O60.0272 (4)0.4964 (5)0.42333 (11)0.0987 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.055 (2)0.044 (2)0.0473 (18)0.0035 (17)0.0050 (17)0.0033 (16)
C20.059 (3)0.053 (2)0.062 (2)0.005 (2)0.006 (2)0.0003 (19)
C30.096 (4)0.071 (3)0.068 (3)0.006 (3)0.028 (3)0.012 (2)
C40.112 (5)0.075 (3)0.050 (2)0.024 (3)0.001 (3)0.007 (2)
C50.087 (4)0.078 (3)0.064 (3)0.005 (3)0.012 (3)0.021 (3)
C60.062 (3)0.049 (2)0.057 (2)0.004 (2)0.0034 (18)0.0095 (18)
C70.068 (3)0.068 (3)0.056 (2)0.005 (2)0.011 (2)0.004 (2)
C80.057 (2)0.044 (2)0.0509 (19)0.0017 (17)0.0004 (17)0.0059 (16)
C90.057 (2)0.056 (2)0.053 (2)0.0113 (18)0.0096 (18)0.0039 (18)
C100.054 (2)0.062 (2)0.0342 (15)0.0002 (19)0.0001 (15)0.0023 (15)
C110.049 (2)0.055 (2)0.0394 (16)0.0018 (17)0.0053 (15)0.0022 (15)
C120.046 (2)0.049 (2)0.0459 (17)0.0078 (17)0.0033 (16)0.0022 (15)
C130.060 (3)0.066 (3)0.057 (2)0.007 (2)0.0011 (19)0.013 (2)
C140.085 (3)0.086 (3)0.050 (2)0.031 (3)0.006 (2)0.010 (2)
C150.099 (4)0.082 (4)0.051 (2)0.028 (3)0.015 (3)0.004 (2)
C160.058 (3)0.081 (3)0.077 (3)0.007 (2)0.019 (2)0.013 (2)
C170.044 (2)0.060 (2)0.062 (2)0.0064 (19)0.0104 (18)0.0037 (19)
S10.0515 (6)0.0560 (6)0.0508 (5)0.0032 (5)0.0041 (4)0.0055 (4)
N10.070 (3)0.064 (2)0.080 (2)0.0302 (19)0.002 (2)0.0077 (19)
N20.0449 (17)0.060 (2)0.0401 (14)0.0036 (15)0.0014 (13)0.0026 (14)
N30.050 (2)0.069 (3)0.081 (2)0.0070 (18)0.0047 (19)0.014 (2)
O10.068 (2)0.128 (3)0.0381 (13)0.030 (2)0.0032 (13)0.0059 (16)
O20.0609 (19)0.147 (4)0.0478 (14)0.039 (2)0.0108 (14)0.0140 (19)
O30.076 (2)0.0584 (18)0.081 (2)0.0064 (17)0.0180 (17)0.0001 (16)
O40.0590 (18)0.102 (3)0.0655 (17)0.0225 (18)0.0054 (15)0.0188 (18)
O50.075 (2)0.118 (3)0.082 (2)0.013 (2)0.010 (2)0.031 (2)
O60.046 (2)0.115 (3)0.135 (3)0.010 (2)0.000 (2)0.015 (3)
Geometric parameters (Å, º) top
C1—C21.377 (6)C11—O11.197 (4)
C1—C61.402 (6)C11—O21.291 (5)
C1—C81.436 (5)C12—C171.375 (5)
C2—C31.390 (7)C12—C131.381 (6)
C2—H2A0.9300C12—S11.796 (4)
C3—C41.396 (8)C13—C141.384 (6)
C3—H3A0.9300C13—H130.9300
C4—C51.350 (8)C14—C151.363 (8)
C4—H40.9300C14—H140.9300
C5—C61.410 (6)C15—C161.364 (8)
C5—H50.9300C15—H150.9300
C6—N11.356 (6)C16—C171.387 (6)
C7—C81.337 (6)C16—H160.9300
C7—N11.376 (6)C17—N31.459 (6)
C7—H70.9300S1—O31.418 (3)
C8—C91.488 (5)S1—O41.426 (3)
C9—C101.533 (6)S1—N21.588 (3)
C9—H9A0.9700N1—H10.8600
C9—H9B0.9700N2—H20.8600
C10—N21.466 (5)N3—O51.195 (5)
C10—C111.509 (5)N3—O61.221 (5)
C10—H100.9800O2—H30.9400
C2—C1—C6118.9 (4)O1—C11—C10124.5 (4)
C2—C1—C8134.6 (4)O2—C11—C10111.9 (3)
C6—C1—C8106.5 (4)C17—C12—C13118.5 (4)
C1—C2—C3119.5 (5)C17—C12—S1125.2 (3)
C1—C2—H2A120.3C13—C12—S1116.1 (3)
C3—C2—H2A120.3C12—C13—C14120.2 (5)
C2—C3—C4120.6 (5)C12—C13—H13119.9
C2—C3—H3A119.7C14—C13—H13119.9
C4—C3—H3A119.7C15—C14—C13119.8 (5)
C5—C4—C3121.5 (4)C15—C14—H14120.1
C5—C4—H4119.3C13—C14—H14120.1
C3—C4—H4119.3C14—C15—C16121.5 (4)
C4—C5—C6117.9 (5)C14—C15—H15119.2
C4—C5—H5121.1C16—C15—H15119.2
C6—C5—H5121.1C15—C16—C17118.2 (5)
N1—C6—C1108.2 (3)C15—C16—H16120.9
N1—C6—C5130.1 (4)C17—C16—H16120.9
C1—C6—C5121.7 (4)C12—C17—C16121.8 (4)
C8—C7—N1110.9 (4)C12—C17—N3121.8 (4)
C8—C7—H7124.5C16—C17—N3116.4 (4)
N1—C7—H7124.5O3—S1—O4120.0 (2)
C7—C8—C1106.3 (4)O3—S1—N2107.77 (18)
C7—C8—C9127.8 (4)O4—S1—N2108.22 (19)
C1—C8—C9125.8 (4)O3—S1—C12105.04 (19)
C8—C9—C10112.1 (3)O4—S1—C12106.84 (19)
C8—C9—H9A109.2N2—S1—C12108.47 (17)
C10—C9—H9A109.2C6—N1—C7108.0 (4)
C8—C9—H9B109.2C6—N1—H1126.0
C10—C9—H9B109.2C7—N1—H1126.0
H9A—C9—H9B107.9C10—N2—S1120.8 (3)
N2—C10—C11110.9 (3)C10—N2—H2119.6
N2—C10—C9110.8 (3)S1—N2—H2119.6
C11—C10—C9109.1 (3)O5—N3—O6124.0 (5)
N2—C10—H10108.7O5—N3—C17119.4 (4)
C11—C10—H10108.7O6—N3—C17116.6 (5)
C9—C10—H10108.7C11—O2—H3114.3
O1—C11—O2123.5 (4)
C6—C1—C2—C30.2 (6)C12—C13—C14—C151.5 (7)
C8—C1—C2—C3179.9 (5)C13—C14—C15—C160.2 (8)
C1—C2—C3—C40.7 (7)C14—C15—C16—C171.6 (8)
C2—C3—C4—C51.2 (8)C13—C12—C17—C160.2 (6)
C3—C4—C5—C60.7 (8)S1—C12—C17—C16175.2 (4)
C2—C1—C6—N1179.9 (4)C13—C12—C17—N3179.9 (4)
C8—C1—C6—N10.1 (5)S1—C12—C17—N35.2 (6)
C2—C1—C6—C50.7 (6)C15—C16—C17—C121.4 (7)
C8—C1—C6—C5179.4 (4)C15—C16—C17—N3178.2 (4)
C4—C5—C6—N1179.3 (5)C17—C12—S1—O3160.3 (4)
C4—C5—C6—C10.2 (7)C13—C12—S1—O314.8 (4)
N1—C7—C8—C11.9 (5)C17—C12—S1—O431.7 (4)
N1—C7—C8—C9178.9 (4)C13—C12—S1—O4143.3 (3)
C2—C1—C8—C7178.9 (5)C17—C12—S1—N284.7 (4)
C6—C1—C8—C71.1 (5)C13—C12—S1—N2100.2 (3)
C2—C1—C8—C91.7 (7)C1—C6—N1—C71.2 (5)
C6—C1—C8—C9178.2 (4)C5—C6—N1—C7179.6 (5)
C7—C8—C9—C10103.7 (5)C8—C7—N1—C62.0 (6)
C1—C8—C9—C1072.8 (5)C11—C10—N2—S1104.3 (3)
C8—C9—C10—N262.1 (4)C9—C10—N2—S1134.4 (3)
C8—C9—C10—C11175.6 (3)O3—S1—N2—C1036.3 (3)
N2—C10—C11—O131.5 (6)O4—S1—N2—C10167.5 (3)
C9—C10—C11—O190.8 (5)C12—S1—N2—C1076.9 (3)
N2—C10—C11—O2151.1 (4)C12—C17—N3—O548.9 (6)
C9—C10—C11—O286.6 (4)C16—C17—N3—O5130.7 (5)
C17—C12—C13—C141.7 (6)C12—C17—N3—O6132.4 (5)
S1—C12—C13—C14177.1 (3)C16—C17—N3—O648.0 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···Cg1i0.862.773.565 (4)155
N2—H2···O1ii0.862.102.918 (4)158
Symmetry codes: (i) x1/2, y+3/2, z+3/4; (ii) y, x, z+1.

Experimental details

Crystal data
Chemical formulaC17H15N3O6S
Mr389.38
Crystal system, space groupTetragonal, P41212
Temperature (K)296
a, c (Å)9.6818 (5), 44.017 (3)
V3)4126.0 (4)
Z8
Radiation typeMo Kα
µ (mm1)0.19
Crystal size (mm)0.30 × 0.25 × 0.10
Data collection
DiffractometerBruker Kappa APEXII CCD
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
4042, 4042, 3492
Rint0.000
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.067, 0.168, 1.07
No. of reflections4042
No. of parameters245
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.21, 0.24
Absolute structureFlack (1983), 1581 Friedel pairs
Absolute structure parameter0.03 (15)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···Cg1i0.862.773.565 (4)155
N2—H2···O1ii0.862.102.918 (4)158
Symmetry codes: (i) x1/2, y+3/2, z+3/4; (ii) y, x, z+1.
 

Acknowledgements

The authors acknowledge the Higher Education Commission of Pakistan for providing a grant for the project to strengthen the Materials Chemistry Laboratory at GC University Lahore, Pakistan.

References

First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationDeng, X. & Mani, N. S. (2006). Green Chem. 8, 835–838.  Web of Science CrossRef CAS
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals
First citationKhan, I. U., Arshad, M. N., Mubashar-ur-Rehman, H., Harrison, W. T. A. & Ali, M. B. (2011a). Acta Cryst. E67, o2325.  Web of Science CSD CrossRef IUCr Journals
First citationKhan, M. H., Khan, I. U., Arshad, M. N., Rafique, H. M. & Harrison, W. T. A. (2011b). Crystals, 1, 69–77.  CSD CrossRef CAS
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals

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