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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 9| September 2011| Pages o2245-o2246
doi:10.1107/S1600536811030601

2-Azido­methyl-3-methyl-1-phenyl­sulfonyl-1H-indole

S. Karthikeyan,a K. Sethusankar,a* Ganesan Gobi Rajeswaranb and Arasambattu K. Mohanakrishnanb

aDepartment of Physics, RKM Vivekananda College (Autonomous), Chennai 600 004, India, and bDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India
*Correspondence e-mail: ksethusankar@yahoo.co.in

(Received 27 July 2011; accepted 29 July 2011; online 6 August 2011)

In the title compound, C16H14N4O2S, the plane of the indole ring is twisted by 70.4 (2)° with respect to the plane of the azidomethyl­ substituent. As a result of the electron-withdrawing character of the phenyl­sulfonyl groups, the N—C bond lengths are slightly longer than the anti­cipated value of approximately 1.355 Å for an N atom with a planar configuration. The indole ring is essentially planar, with a maximum deviation of 0.0296 Å. The azide group is almost linear, the N—N—N angle being 171.4 (3)°. The methyl group on the azide-substituted C atom is in a flagpole position. The phenyl ring of the sulfonyl substituent makes a dihedral angle of 87.07 (10)° with the best plane of the indole moiety. The crystal packing is stabilized by inter­molecular C—H⋯O inter­actions, which link the mol­ecules into infinite chains running parallel to the b axis. The crystal packing is further stabilized by C—H⋯π inter­actions.

Related literature

For the biological activity of compounds containing an indole ring system, sulfur and azides, see: Williams et al. (1993[Williams, T. M., Ciccarone, T. M., MacTough, S. C., Rooney, C. S., Balani, S. K., Condra, J. H., Emini, E. A., Goldman, M. E., Greenlee, W. J. & Kauffman, L. R. (1993). J. Med. Chem. 36, 1291-1294.]); Amblard et al. (2009[Amblard, F., Cho, J. H. & Schhinazi, R. F. (2009). Chem. Rev. 109, 4207-4220.]); De-Benedetti et al. (1985[De-Benedetti, P. G., Folli, U., Iarossi, D. & Frassineti, C. (1985). J. Chem. Soc. Perkin Trans. 2, pp. 1527-1532.]). For related structures, see: Fernandes et al. (2005[Fernandes, M. A., de Koning, C. B., Michael, J. P. & Petersen, R. L. (2005). Acta Cryst. E61, o269-o271.]). For comparison of mol­ecular dimensions, see: Bassindale (1984[Bassindale, A. (1984). The Third Dimension in Organic Chemistry, ch. 1, p. 11. New York: John Wiley and Sons.]); Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data

  • C16H14N4O2S

  • Mr = 326.38

  • Orthorhombic, P b c a

  • a = 11.0337 (4) Å

  • b = 12.1424 (4) Å

  • c = 23.2234 (9) Å

  • V = 3111.37 (19) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.22 mm−1

  • T = 295 K

  • 0.30 × 0.25 × 0.25 mm
Data collection

  • Bruker Kappa APEXII CCD diffractometer

  • 37510 measured reflections

  • 4231 independent reflections

  • 2776 reflections with I > 2σ(I)

  • Rint = 0.049
Refinement

  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 0.166

  • S = 0.99

  • 4231 reflections

  • 209 parameters

  • H-atom parameters constrained

  • Δρmax = 0.37 e Å−3

  • Δρmin = −0.35 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C11–C16 ring.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
C14—H14⋯O1i 0.93 2.46 3.322 (3) 154
C5—H5⋯Cg3ii 0.93 2.89 3.714 (3) 148
Symmetry codes: (i) [-x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]; (ii) -x, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). 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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811030601/rk2287sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811030601/rk2287Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811030601/rk2287Isup3.cml

checkCIF report


Comment top

The phenylsulfonyl indole compounds inhibit the HIV–1 RT enzyme in vitro and HTLVIIIb viral spread in MT–4 human T–lymphoid cells (Williams, et al., 1993). The Cu(I)–catalyzed 1,3–dipolar cycloaddition reaction between alkynes and azides has been suitable for the synthesis of a large number of modified nucleosides, nucleotides and oligonucleotides with a broad range of applications (Amblard et al., 2009). A lot of sulfur containing compounds, exhibit insecticidal, germicidal, antimicrobial and antibacterial activities (De-Benedetti et al., 1985).

In the title compound C16H14N4O2S, the molecular conformation (Fig. 1) is preferred with the plane of indole ring twisted by 70.4 (2)° with respect to the plane of the azido group bound to the methyl substituent. The indole ring is essentially planar with a maximum deviation 0.0296 (17)Å for the atom N1. The bond angle around N3, in the chain of atom N2–N3–N4, is 171.4 (3)° and thus the azidomethyl side chain is almost linear. The methyl group on the azide substituted C atom is in a flag pole position.

The phenyl ring of the sulfonyl substituent makes a dihedral angle of 87.07 (10)° with the indole moiety. The deviation of atoms S1 and C10 from the indole mean plane is 0.453 (5)Å and -0.0618 (24)Å, respectively. As a result of electron–withdrawing character of the phenylsulfonyl group, the bond lengths N1—C8 = 1.432 (2)Å and N1—C1 = 1.416 (2)Å in the molecule are longer than the mean value of 1.355 (14)Å (Allen et al., 1987). Due to Thorpe–Ingold effect (Bassindale, 1984), bond angles around atom S1 show significant deviations from the ideal tetrahedral value, with significant deviations, widening of angle O1═S1═O2 = 119.71 (10)° and narrowing of angle N1—S1—C11 = 105.36 (8)°. The title molecule exhibits structural similarities with the already reported related structure (Fernandes et al., 2005).

In crystal packing, the molecule is stabilized by intermolecular C—H···O interactions which link the molecules into infinite chains running parallel to b axis. The crystal packing is further stabilized by C—H···π interaction, where Cg3 is centroid of C11–C16. The symmetry codes: (i) -1/2-x, 1/2+y, z; (ii) -x, 1-y, 1-z. The packing view of the title compound is shown in the Fig. 2.

Related literature top

For the biological activity of compounds containing an indole ring system, sulfur, azides, see: Williams et al. (1993); Amblard et al. (2009); De-Benedetti et al. (1985). For related structures, see: Fernandes et al. (2005). For comparison of molecular dimensions, see: Bassindale (1984); Allen et al. (1987).

Experimental top

To a solution of 2–(bromomethyl)–3–methyl–1–phenylsulfonyl–indole (1 mmol) in DMF (3 ml) was added sodium azide (2 mmol) and stirred for 2 h at room temperature. After consumption of the 2–(bromomethyl)–3–methyl–1–phenylsulfonyl–indole (monitored by TLC), reaction mass was poured into ice water (20 ml). The solid obtained was filtered and dried (CaSO4). Then the crude product was recrystalized with MeOH (5 ml) afforded the 2–(azidomethyl)–3–methyl–1–phenylsulfonyl–indole as a colourless solid. Yield: 0.28 g (92%).

Refinement top

All the hydrogen atoms in the molecule were placed geometrically and allowed to ride on their parent atoms with C—H distance in the range 0.93Å to 0.97Å and with Uiso(H) = 1.5Ueq(C) for CH3 group and Uiso(H) = 1.2Ueq(C) for all the other groups.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (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. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at 30% probability level. H atoms are present as a small spheres of arbitary radius.
[Figure 2] Fig. 2. The packing arrangement of the title compound viewed down a axis. The dashed lines indicate C—H···O intermolecular interactions, which is running parallel to b axis. Initial symmetry code: (i) -1/2-x, 1/2+y, z.
2-Azidomethyl-3-methyl-1-phenylsulfonyl-1H-indole top
Crystal data top
C16H14N4O2SF(000) = 1360
Mr = 326.38Dx = 1.393 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 4231 reflections
a = 11.0337 (4) Åθ = 1.0–29.3°
b = 12.1424 (4) ŵ = 0.22 mm−1
c = 23.2234 (9) ÅT = 295 K
V = 3111.37 (19) Å3Block, colourless
Z = 80.30 × 0.25 × 0.25 mm
Data collection top
Bruker Kappa APEXII CCD
diffractometer		2776 reflections with I > 2σ(I)
Radiation source: fine–focus sealed tubeRint = 0.049
Graphite monochromatorθmax = 29.3°, θmin = 2.6°
ω scansh = −15→13
37510 measured reflectionsk = −16→12
4231 independent reflectionsl = −31→31
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.166H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.0987P)2 + 0.4179P]
where P = (Fo2 + 2Fc2)/3
4231 reflections(Δ/σ)max < 0.001
209 parametersΔρmax = 0.37 e Å−3
0 restraintsΔρmin = −0.35 e Å−3
Crystal data top
C16H14N4O2SV = 3111.37 (19) Å3
Mr = 326.38Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 11.0337 (4) ŵ = 0.22 mm−1
b = 12.1424 (4) ÅT = 295 K
c = 23.2234 (9) Å0.30 × 0.25 × 0.25 mm
Data collection top
Bruker Kappa APEXII CCD
diffractometer		2776 reflections with I > 2σ(I)
37510 measured reflectionsRint = 0.049
4231 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.166H-atom parameters constrained
S = 0.99Δρmax = 0.37 e Å−3
4231 reflectionsΔρmin = −0.35 e Å−3
209 parameters
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
C10.07440 (17)0.32220 (15)0.44968 (8)0.0419 (4)
C2−0.0143 (2)0.25607 (19)0.47362 (10)0.0566 (5)
H2−0.05690.20520.45160.068*
C3−0.0368 (3)0.2688 (2)0.53153 (12)0.0719 (7)
H3−0.09580.22530.54880.086*
C40.0252 (3)0.3435 (3)0.56443 (11)0.0807 (8)
H40.00750.34950.60340.097*
C50.1128 (2)0.4095 (2)0.54104 (10)0.0690 (7)
H50.15480.46000.56360.083*
C60.13730 (18)0.39903 (16)0.48237 (9)0.0478 (5)
C70.22068 (19)0.45506 (16)0.44500 (9)0.0513 (5)
C80.20845 (16)0.41425 (15)0.39159 (8)0.0424 (4)
C90.3091 (3)0.5412 (2)0.46516 (13)0.0844 (9)
H9A0.33900.58160.43260.127*
H9B0.37560.50620.48460.127*
H9C0.26910.59080.49120.127*
C100.2829 (2)0.4427 (2)0.34045 (9)0.0529 (5)
H10A0.31100.51810.34410.064*
H10B0.23280.43820.30620.064*
C11−0.08441 (17)0.36552 (16)0.33108 (8)0.0433 (4)
C12−0.0704 (2)0.46737 (18)0.30491 (9)0.0547 (5)
H120.00480.48930.29100.066*
C13−0.1695 (3)0.5355 (2)0.29992 (11)0.0711 (7)
H13−0.16150.60430.28280.085*
C14−0.2791 (3)0.5020 (3)0.32010 (13)0.0801 (9)
H14−0.34570.54840.31640.096*
C15−0.2932 (2)0.4012 (3)0.34580 (12)0.0780 (8)
H15−0.36900.37970.35920.094*
C16−0.19488 (19)0.3311 (2)0.35192 (11)0.0609 (6)
H16−0.20330.26280.36960.073*
N10.12022 (14)0.32780 (13)0.39281 (6)0.0405 (3)
N20.38932 (18)0.3686 (2)0.33357 (9)0.0696 (6)
N30.37305 (17)0.2784 (2)0.31151 (9)0.0632 (5)
N40.3730 (2)0.1938 (2)0.29245 (13)0.0975 (8)
O10.00404 (15)0.17244 (11)0.35322 (7)0.0599 (4)
O20.11681 (14)0.29357 (13)0.28769 (6)0.0590 (4)
S10.04241 (4)0.27961 (4)0.33704 (2)0.04300 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0427 (10)0.0382 (9)0.0449 (10)−0.0001 (8)0.0005 (8)0.0030 (7)
C20.0576 (13)0.0529 (11)0.0593 (13)−0.0137 (10)0.0052 (10)0.0041 (10)
C30.0766 (17)0.0759 (17)0.0633 (15)−0.0133 (13)0.0191 (13)0.0112 (12)
C40.103 (2)0.0881 (19)0.0509 (14)−0.0151 (17)0.0197 (14)−0.0017 (12)
C50.0830 (17)0.0747 (15)0.0494 (12)−0.0168 (14)0.0032 (12)−0.0107 (11)
C60.0500 (11)0.0466 (11)0.0468 (10)−0.0046 (9)−0.0014 (8)−0.0035 (8)
C70.0491 (11)0.0467 (11)0.0580 (12)−0.0103 (9)−0.0008 (9)−0.0061 (9)
C80.0363 (9)0.0417 (9)0.0490 (10)−0.0026 (7)−0.0004 (7)0.0029 (7)
C90.0866 (19)0.0825 (18)0.0841 (19)−0.0432 (16)0.0045 (15)−0.0183 (14)
C100.0471 (11)0.0592 (12)0.0524 (12)−0.0067 (10)0.0018 (9)0.0077 (9)
C110.0385 (9)0.0463 (10)0.0452 (10)0.0038 (8)−0.0076 (8)−0.0100 (8)
C120.0605 (13)0.0535 (12)0.0501 (11)0.0067 (10)−0.0110 (10)−0.0028 (9)
C130.089 (2)0.0627 (14)0.0613 (14)0.0285 (14)−0.0205 (13)−0.0114 (11)
C140.0729 (19)0.089 (2)0.0786 (18)0.0410 (16)−0.0250 (15)−0.0325 (15)
C150.0385 (12)0.107 (2)0.0881 (19)0.0117 (13)−0.0040 (11)−0.0294 (16)
C160.0414 (11)0.0694 (15)0.0719 (14)0.0003 (10)−0.0048 (10)−0.0123 (11)
N10.0381 (8)0.0434 (8)0.0400 (8)−0.0047 (6)−0.0029 (6)0.0015 (6)
N20.0389 (10)0.0972 (17)0.0728 (14)−0.0009 (11)0.0019 (9)−0.0075 (11)
N30.0461 (10)0.0842 (17)0.0594 (12)0.0081 (11)0.0006 (9)0.0063 (11)
N40.0768 (17)0.0868 (18)0.129 (2)0.0254 (14)−0.0104 (16)−0.0159 (17)
O10.0639 (10)0.0375 (8)0.0783 (10)−0.0019 (7)−0.0153 (8)−0.0086 (7)
O20.0488 (8)0.0817 (11)0.0463 (8)0.0069 (7)0.0009 (6)−0.0149 (7)
S10.0380 (3)0.0433 (3)0.0478 (3)0.00322 (19)−0.00599 (19)−0.00836 (18)
Geometric parameters (Å, º) top
C1—C21.383 (3)C10—H10A0.9700
C1—C61.389 (3)C10—H10B0.9700
C1—N11.416 (2)C11—C161.377 (3)
C2—C31.376 (4)C11—C121.387 (3)
C2—H20.9300C11—S11.7509 (19)
C3—C41.369 (4)C12—C131.376 (3)
C3—H30.9300C12—H120.9300
C4—C51.368 (4)C13—C141.359 (4)
C4—H40.9300C13—H130.9300
C5—C61.395 (3)C14—C151.371 (4)
C5—H50.9300C14—H140.9300
C6—C71.436 (3)C15—C161.386 (3)
C7—C81.342 (3)C15—H150.9300
C7—C91.505 (3)C16—H160.9300
C8—N11.432 (2)N1—S11.6604 (15)
C8—C101.485 (3)N2—N31.222 (3)
C9—H9A0.9600N3—N41.119 (3)
C9—H9B0.9600O1—S11.4190 (16)
C9—H9C0.9600O2—S11.4200 (15)
C10—N21.488 (3)
C2—C1—C6121.61 (19)C8—C10—H10B109.1
C2—C1—N1130.98 (18)N2—C10—H10B109.1
C6—C1—N1107.41 (16)H10A—C10—H10B107.9
C3—C2—C1117.1 (2)C16—C11—C12121.6 (2)
C3—C2—H2121.5C16—C11—S1119.92 (17)
C1—C2—H2121.5C12—C11—S1118.48 (16)
C4—C3—C2122.0 (2)C13—C12—C11119.0 (2)
C4—C3—H3119.0C13—C12—H12120.5
C2—C3—H3119.0C11—C12—H12120.5
C5—C4—C3121.3 (2)C14—C13—C12119.9 (3)
C5—C4—H4119.4C14—C13—H13120.0
C3—C4—H4119.4C12—C13—H13120.0
C4—C5—C6118.1 (2)C13—C14—C15121.2 (2)
C4—C5—H5120.9C13—C14—H14119.4
C6—C5—H5120.9C15—C14—H14119.4
C1—C6—C5119.90 (19)C14—C15—C16120.3 (3)
C1—C6—C7107.95 (17)C14—C15—H15119.9
C5—C6—C7132.2 (2)C16—C15—H15119.9
C8—C7—C6108.61 (17)C11—C16—C15118.0 (3)
C8—C7—C9127.5 (2)C11—C16—H16121.0
C6—C7—C9123.8 (2)C15—C16—H16121.0
C7—C8—N1108.70 (16)C1—N1—C8107.24 (14)
C7—C8—C10126.69 (18)C1—N1—S1121.74 (13)
N1—C8—C10124.23 (17)C8—N1—S1126.47 (12)
C7—C9—H9A109.5N3—N2—C10118.10 (19)
C7—C9—H9B109.5N4—N3—N2171.4 (3)
H9A—C9—H9B109.5O1—S1—O2119.71 (10)
C7—C9—H9C109.5O1—S1—N1105.72 (9)
H9A—C9—H9C109.5O2—S1—N1106.78 (9)
H9B—C9—H9C109.5O1—S1—C11109.20 (10)
C8—C10—N2112.42 (17)O2—S1—C11109.09 (9)
C8—C10—H10A109.1N1—S1—C11105.36 (8)
N2—C10—H10A109.1
C6—C1—C2—C3−0.7 (3)C13—C14—C15—C160.3 (4)
N1—C1—C2—C3178.5 (2)C12—C11—C16—C150.3 (3)
C1—C2—C3—C40.1 (4)S1—C11—C16—C15−179.36 (17)
C2—C3—C4—C50.1 (5)C14—C15—C16—C11−0.6 (4)
C3—C4—C5—C60.2 (4)C2—C1—N1—C8177.9 (2)
C2—C1—C6—C51.0 (3)C6—C1—N1—C8−2.8 (2)
N1—C1—C6—C5−178.3 (2)C2—C1—N1—S120.4 (3)
C2—C1—C6—C7−179.01 (19)C6—C1—N1—S1−160.34 (14)
N1—C1—C6—C71.6 (2)C7—C8—N1—C13.1 (2)
C4—C5—C6—C1−0.8 (4)C10—C8—N1—C1176.49 (18)
C4—C5—C6—C7179.3 (2)C7—C8—N1—S1159.22 (15)
C1—C6—C7—C80.3 (2)C10—C8—N1—S1−27.4 (3)
C5—C6—C7—C8−179.7 (2)C8—C10—N2—N380.5 (3)
C1—C6—C7—C9−177.3 (2)C1—N1—S1—O1−48.72 (17)
C5—C6—C7—C92.7 (4)C8—N1—S1—O1158.31 (15)
C6—C7—C8—N1−2.1 (2)C1—N1—S1—O2−177.23 (14)
C9—C7—C8—N1175.4 (2)C8—N1—S1—O229.80 (18)
C6—C7—C8—C10−175.29 (19)C1—N1—S1—C1166.85 (16)
C9—C7—C8—C102.2 (4)C8—N1—S1—C11−86.12 (17)
C7—C8—C10—N291.2 (3)C16—C11—S1—O112.21 (19)
N1—C8—C10—N2−81.0 (2)C12—C11—S1—O1−167.48 (15)
C16—C11—C12—C130.2 (3)C16—C11—S1—O2144.74 (17)
S1—C11—C12—C13179.90 (16)C12—C11—S1—O2−34.96 (17)
C11—C12—C13—C14−0.5 (3)C16—C11—S1—N1−100.94 (17)
C12—C13—C14—C150.3 (4)C12—C11—S1—N179.36 (16)
Hydrogen-bond geometry (Å, º) top
Cg3 is the centroid of the C11–C16 ring.
D—H···AD—HH···AD···AD—H···A
C14—H14···O1i0.932.463.322 (3)154
C5—H5···Cg3ii0.932.893.714 (3)148
Symmetry codes: (i) −x−1/2, y+1/2, z; (ii) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formulaC16H14N4O2S
Mr326.38
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)295
a, b, c (Å)11.0337 (4), 12.1424 (4), 23.2234 (9)
V (Å3)3111.37 (19)
Z8
Radiation typeMo Kα
µ (mm−1)0.22
Crystal size (mm)0.30 × 0.25 × 0.25
Data collection
DiffractometerBruker Kappa APEXII CCD
diffractometer
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		37510, 4231, 2776
Rint0.049
(sin θ/λ)max (Å−1)0.687
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.166, 0.99
No. of reflections4231
No. of parameters209
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.37, −0.35

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

Hydrogen-bond geometry (Å, º) top
Cg3 is the centroid of the C11–C16 ring.
D—H···AD—HH···AD···AD—H···A
C14—H14···O1i0.932.463.322 (3)154.2
C5—H5···Cg3ii0.932.893.714 (3)148
Symmetry codes: (i) −x−1/2, y+1/2, z; (ii) −x, −y+1, −z+1.
 

Acknowledgements

SK and KS thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the X–ray intensity data collection and Dr V. Murugan, Head of the Department of Physics, RKM Vivekananda College, for providing facilities in the department for carrying out this work.

References

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 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWilliams, T. M., Ciccarone, T. M., MacTough, S. C., Rooney, C. S., Balani, S. K., Condra, J. H., Emini, E. A., Goldman, M. E., Greenlee, W. J. & Kauffman, L. R. (1993). J. Med. Chem. 36, 1291–1294.  CrossRef CAS PubMed Web of Science Google Scholar

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ISSN: 2056-9890
Volume 67| Part 9| September 2011| Pages o2245-o2246
doi:10.1107/S1600536811030601
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