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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 68| Part 10| October 2012| Page o2845
https://doi.org/10.1107/S1600536812036914

1-(2,4-Di­nitro­phen­yl)-3-phenyl-4-phenyl­sulfanyl-1H-pyrazole

V. Susindran,a S. Athimoolam,b* S. Asath Bahadur,a R. Manikannanc and S. Muthusubramanianc

aDepartment of Physics, Kalasalingam University, Anand Nagar, Krishnan Koil 626 190, India, bDepartment of Physics, University College of Engineering Nagercoil, Anna University Chennai, Nagercoil 629 004, India, and cDepartment of Organic Chemistry, Madurai Kamaraj University, Madurai 625 021, India
*Correspondence e-mail: athi81s@yahoo.co.in

(Received 30 May 2012; accepted 27 August 2012; online 5 September 2012)

In the title mol­ecule, C21H14N4O4S, the pyrazole ring forms dihedral angles of 45.6 (1), 87.7 (1) and 27.4 (1)° with the phenyl, sulfur-substituted benzene and nitro-substituted benzene rings, respectively. In the crystal, mol­ecules are connected by weak C—H⋯O and C—H⋯N hydrogen bonds into layers parallel to (010).

Related literature

For the pharmacological and medicinal properties of pyrazole compounds, see: Baraldi et al. (1998[Baraldi, P. G., Manfredini, S., Romagnoli, R., Stevanato, L., Zaid, A. N. & Manservigi, R. (1998). Nucleosides Nucleotides, 17, 2165-2171.]); Bruno et al. (1990[Bruno, O., Bondavalli, F., Ranise, A., Schenone, P., Losasso, C., Cilenti, L., Matera, C. & Marmo, E. (1990). Il Farmaco, 45, 147-66.]); Chen & Li (1998[Chen, H. S. & Li, Z. M. (1998). Chem. J. Chin. Univ. 19, 572-576.]); Cottineau et al. (2002[Cottineau, B., Toto, P., Marot, C., Pipaud, A. & Chenault, J. (2002). Bioorg. Med. Chem. 12, 2105-2108.]); Londershausen (1996[Londershausen, M. (1996). Pestic. Sci. 48, 269-274.]); Mishra et al. (1998[Mishra, P. D., Wahidullah, S. & Kamat, S. Y. (1998). Indian J. Chem. Sect. B, 37, 199-200.]); Smith et al. (2001[Smith, S. R., Denhardt, G. & Terminelli, C. (2001). Eur. J. Pharmacol. 432, 107-119.]).

[Scheme 1]

Experimental

Crystal data

  • C21H14N4O4S

  • Mr = 418.42

  • Monoclinic, P 21 /n

  • a = 7.3062 (4) Å

  • b = 26.5212 (13) Å

  • c = 10.3361 (5) Å

  • β = 104.012 (1)°

  • V = 1943.22 (17) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.20 mm−1

  • T = 293 K

  • 0.24 × 0.21 × 0.18 mm
Data collection

  • Bruker SMART APEX CCD diffractometer

  • 18559 measured reflections

  • 3426 independent reflections

  • 3128 reflections with I > 2σ(I)

  • Rint = 0.021
Refinement

  • R[F2 > 2σ(F2)] = 0.035

  • wR(F2) = 0.091

  • S = 1.04

  • 3426 reflections

  • 271 parameters

  • H-atom parameters constrained

  • Δρmax = 0.27 e Å−3

  • Δρmin = −0.14 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C35—H35⋯O42i 0.93 2.58 3.452 (2) 157
C5—H5⋯N2ii 0.93 2.52 3.411 (2) 161
Symmetry codes: (i) x, y, z+1; (ii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: SMART (Bruker, 2001[Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812036914/lh5484sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812036914/lh5484Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812036914/lh5484Isup3.cml

checkCIF report


Comment top

Pyrazoles are a class of aromatic ring compounds and of the heterocyclic series characterized by a 5-membered ring structure composed of three carbon atoms and two nitrogen atoms in adjacent positions and to the unsubstituted parent compound. They can have pharmacological effects on humans and are classified as alkaloids although they are rare in nature. Pyrazole and its derivatives have successfully tested for antifungal (Chen & Li, 1998), antihistaminic (Mishra et al.,1998), anti-inflammatory (Smith et al., 2001), antiarrhythmic and sedative (Bruno et al., 1990), hypoglycemic (Cottineau et al., 2002), antiviral (Baraldi et al., 1998) and pesticidal (Londershausen, 1996) activities.

The molecular structure of the title compound is shown in Fig. 1. The pyrazole ring forms dihedral angles of 27.4 (1)° (with the C11-C16 ring), 45.6 (1)° (with the C31-C36 ring) and 87.7 (1)° (with the C41-C46 ring). In the nitrophenyl group, the nitro substituents are twisted from the benzen ring by 13.9 (2)° and 43.2 (1)°. In the crystal, molecules are connected by weak C—H···O and C—H···N hydrogen bonds into layers parallel to (010) (see Fig. 2).

Related literature top

For the pharmacological and medicinal properties of pyrazole compounds, see: Baraldi et al. (1998); Bruno et al. (1990); Chen & Li (1998); Cottineau et al. (2002); Londershausen (1996); Mishra et al. (1998); Smith et al. (2001).

Experimental top

A mixture of 1-phenyl-2-(phenylsulfanyl)-1-ethanone 1-(2,4-dinitrophenyl)hydrazone (0.001 mole) dissolved in dimethylforamide (5 ml) in a 30 ml conical flask was allowed to cool in ice with stirring. To this stirred solution, phosphorus oxychloride (0.008 mole) was added dropwise and the mixture was subjected to microwave irradiation for 30 sec. The reaction was monitored by TLC and after completion of the reaction, the reaction mixture was poured onto crushed ice. The solid was suction filtered and washed with plenty of water. The final product 1-(2,4-dinitrophenyl)-3-phenyl-4-(phenylsulfanyl)-1H-pyrazole was purified by column chromatography using petroleum ether-ethyl acetate as eluent. Colourless needles were grown over a period of a week from a solution of the title compound in dichlromethane.

Refinement top

All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93 Å and Uiso(H) = 1.2 Ueq(C).

Structure description top

Pyrazoles are a class of aromatic ring compounds and of the heterocyclic series characterized by a 5-membered ring structure composed of three carbon atoms and two nitrogen atoms in adjacent positions and to the unsubstituted parent compound. They can have pharmacological effects on humans and are classified as alkaloids although they are rare in nature. Pyrazole and its derivatives have successfully tested for antifungal (Chen & Li, 1998), antihistaminic (Mishra et al.,1998), anti-inflammatory (Smith et al., 2001), antiarrhythmic and sedative (Bruno et al., 1990), hypoglycemic (Cottineau et al., 2002), antiviral (Baraldi et al., 1998) and pesticidal (Londershausen, 1996) activities.

The molecular structure of the title compound is shown in Fig. 1. The pyrazole ring forms dihedral angles of 27.4 (1)° (with the C11-C16 ring), 45.6 (1)° (with the C31-C36 ring) and 87.7 (1)° (with the C41-C46 ring). In the nitrophenyl group, the nitro substituents are twisted from the benzen ring by 13.9 (2)° and 43.2 (1)°. In the crystal, molecules are connected by weak C—H···O and C—H···N hydrogen bonds into layers parallel to (010) (see Fig. 2).

For the pharmacological and medicinal properties of pyrazole compounds, see: Baraldi et al. (1998); Bruno et al. (1990); Chen & Li (1998); Cottineau et al. (2002); Londershausen (1996); Mishra et al. (1998); Smith et al. (2001).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. Part of the crystal structure with hydrogen bonds shown as dashed lines.
1-(2,4-Dinitrophenyl)-3-phenyl-4-phenylsulfanyl-1H-pyrazole top
Crystal data top
C21H14N4O4SF(000) = 864
Mr = 418.42Dx = 1.430 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4527 reflections
a = 7.3062 (4) Åθ = 2.1–24.4°
b = 26.5212 (13) ŵ = 0.20 mm−1
c = 10.3361 (5) ÅT = 293 K
β = 104.012 (1)°Block, colourless
V = 1943.22 (17) Å30.24 × 0.21 × 0.18 mm
Z = 4
Data collection top
Bruker SMART APEX CCD
diffractometer		3128 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.021
Graphite monochromatorθmax = 25.0°, θmin = 1.5°
ω scansh = −8→8
18559 measured reflectionsk = −31→31
3426 independent reflectionsl = −12→12
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)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0451P)2 + 0.5673P]
where P = (Fo2 + 2Fc2)/3
3426 reflections(Δ/σ)max < 0.001
271 parametersΔρmax = 0.27 e Å−3
0 restraintsΔρmin = −0.14 e Å−3
Crystal data top
C21H14N4O4SV = 1943.22 (17) Å3
Mr = 418.42Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.3062 (4) ŵ = 0.20 mm−1
b = 26.5212 (13) ÅT = 293 K
c = 10.3361 (5) Å0.24 × 0.21 × 0.18 mm
β = 104.012 (1)°
Data collection top
Bruker SMART APEX CCD
diffractometer		3128 reflections with I > 2σ(I)
18559 measured reflectionsRint = 0.021
3426 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0350 restraints
wR(F2) = 0.091H-atom parameters constrained
S = 1.04Δρmax = 0.27 e Å−3
3426 reflectionsΔρmin = −0.14 e Å−3
271 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
N10.41540 (17)0.26466 (4)0.02430 (12)0.0380 (3)
C110.4691 (2)0.31285 (5)−0.01058 (15)0.0379 (3)
C120.5120 (2)0.34984 (6)0.08788 (16)0.0466 (4)
H120.50590.34210.17450.056*
C130.5635 (3)0.39766 (6)0.05891 (17)0.0510 (4)
H130.59690.42170.12590.061*
C140.5647 (2)0.40930 (6)−0.07041 (17)0.0458 (4)
C150.5206 (2)0.37446 (6)−0.17104 (16)0.0453 (4)
H150.51970.3832−0.25830.054*
C160.4775 (2)0.32614 (6)−0.13962 (15)0.0407 (3)
N30.6219 (2)0.46010 (6)−0.10176 (19)0.0597 (4)
O310.5928 (2)0.47181 (5)−0.21916 (17)0.0820 (5)
O320.6962 (2)0.48746 (5)−0.00956 (17)0.0849 (5)
N40.4608 (2)0.28911 (6)−0.24824 (15)0.0546 (4)
O410.3765 (2)0.30239 (6)−0.35976 (13)0.0816 (5)
O420.5384 (2)0.24840 (5)−0.22055 (15)0.0727 (4)
N20.48161 (17)0.24827 (4)0.15338 (12)0.0385 (3)
C30.4084 (2)0.20278 (5)0.15590 (14)0.0363 (3)
C310.4517 (2)0.17255 (5)0.27946 (14)0.0379 (3)
C320.4992 (2)0.12194 (6)0.27580 (16)0.0447 (4)
H320.50160.10700.19480.054*
C330.5428 (3)0.09357 (6)0.39095 (17)0.0518 (4)
H330.57530.05980.38750.062*
C340.5382 (3)0.11532 (7)0.51093 (17)0.0565 (5)
H340.56730.09620.58860.068*
C350.4907 (2)0.16534 (7)0.51629 (16)0.0536 (4)
H350.48790.17990.59770.064*
C360.4472 (2)0.19411 (6)0.40134 (15)0.0439 (4)
H360.41490.22790.40550.053*
C40.2922 (2)0.18993 (5)0.02874 (14)0.0380 (3)
S10.15552 (6)0.135789 (14)−0.01962 (4)0.04436 (13)
C410.3132 (2)0.09507 (6)−0.07662 (15)0.0454 (4)
C420.4896 (3)0.10892 (7)−0.08882 (18)0.0576 (4)
H420.53460.1413−0.06560.069*
C430.5999 (3)0.07424 (9)−0.1360 (2)0.0716 (6)
H430.71960.0834−0.14370.086*
C440.5341 (4)0.02652 (9)−0.1715 (2)0.0768 (6)
H440.60870.0035−0.20340.092*
C450.3590 (4)0.01295 (8)−0.1596 (2)0.0745 (6)
H450.3141−0.0193−0.18410.089*
C460.2477 (3)0.04661 (6)−0.11152 (18)0.0588 (5)
H460.12910.0369−0.10250.071*
C50.2996 (2)0.23037 (5)−0.05062 (15)0.0387 (3)
H50.23670.2338−0.13990.046*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0427 (7)0.0330 (6)0.0352 (6)−0.0002 (5)0.0035 (5)−0.0003 (5)
C110.0379 (8)0.0341 (7)0.0398 (8)0.0013 (6)0.0060 (6)−0.0006 (6)
C120.0599 (10)0.0391 (8)0.0402 (9)−0.0022 (7)0.0109 (7)−0.0027 (7)
C130.0608 (10)0.0377 (8)0.0527 (10)−0.0039 (7)0.0099 (8)−0.0083 (7)
C140.0438 (9)0.0337 (8)0.0589 (10)−0.0004 (6)0.0107 (7)0.0027 (7)
C150.0428 (8)0.0487 (9)0.0446 (9)−0.0008 (7)0.0108 (7)0.0065 (7)
C160.0396 (8)0.0420 (8)0.0397 (8)−0.0025 (6)0.0082 (6)−0.0050 (6)
N30.0548 (9)0.0419 (8)0.0835 (12)0.0016 (7)0.0189 (8)0.0118 (8)
O310.0934 (11)0.0606 (9)0.0907 (11)−0.0049 (8)0.0199 (9)0.0289 (8)
O320.1012 (12)0.0454 (8)0.1062 (12)−0.0240 (8)0.0213 (9)−0.0121 (8)
N40.0597 (9)0.0609 (10)0.0481 (9)−0.0199 (7)0.0225 (7)−0.0143 (7)
O410.1011 (11)0.1023 (12)0.0392 (7)−0.0322 (9)0.0129 (7)−0.0093 (7)
O420.0884 (10)0.0552 (8)0.0825 (10)−0.0049 (7)0.0366 (8)−0.0259 (7)
N20.0425 (7)0.0372 (7)0.0334 (6)−0.0002 (5)0.0043 (5)−0.0010 (5)
C30.0366 (7)0.0344 (7)0.0371 (8)0.0020 (6)0.0074 (6)−0.0021 (6)
C310.0361 (7)0.0401 (8)0.0359 (8)−0.0031 (6)0.0056 (6)−0.0009 (6)
C320.0518 (9)0.0427 (8)0.0379 (8)0.0027 (7)0.0076 (7)−0.0020 (6)
C330.0608 (10)0.0427 (9)0.0481 (10)0.0021 (8)0.0057 (8)0.0061 (7)
C340.0648 (11)0.0596 (11)0.0404 (9)−0.0086 (9)0.0032 (8)0.0107 (8)
C350.0606 (10)0.0646 (11)0.0345 (8)−0.0125 (9)0.0097 (7)−0.0057 (7)
C360.0448 (9)0.0433 (8)0.0422 (8)−0.0065 (7)0.0078 (7)−0.0064 (7)
C40.0390 (8)0.0343 (7)0.0384 (8)−0.0003 (6)0.0052 (6)−0.0029 (6)
S10.0456 (2)0.0389 (2)0.0466 (2)−0.00736 (16)0.00724 (17)−0.00609 (16)
C410.0594 (10)0.0408 (8)0.0329 (8)0.0021 (7)0.0050 (7)−0.0023 (6)
C420.0671 (12)0.0552 (10)0.0534 (10)−0.0013 (9)0.0199 (9)−0.0060 (8)
C430.0754 (13)0.0867 (15)0.0574 (12)0.0130 (11)0.0250 (10)−0.0043 (11)
C440.1021 (18)0.0722 (14)0.0556 (12)0.0298 (13)0.0180 (11)−0.0104 (10)
C450.1061 (18)0.0479 (11)0.0631 (12)0.0123 (11)0.0081 (12)−0.0130 (9)
C460.0742 (12)0.0433 (9)0.0542 (10)−0.0012 (8)0.0061 (9)−0.0061 (8)
C50.0406 (8)0.0367 (7)0.0353 (8)0.0014 (6)0.0025 (6)−0.0025 (6)
Geometric parameters (Å, º) top
N1—C51.3508 (18)C32—H320.9300
N1—N21.3749 (17)C33—C341.375 (3)
N1—C111.4093 (18)C33—H330.9300
C11—C121.393 (2)C34—C351.376 (3)
C11—C161.395 (2)C34—H340.9300
C12—C131.376 (2)C35—C361.383 (2)
C12—H120.9300C35—H350.9300
C13—C141.374 (2)C36—H360.9300
C13—H130.9300C4—C51.359 (2)
C14—C151.370 (2)C4—S11.7515 (14)
C14—N31.470 (2)S1—C411.7805 (17)
C15—C161.377 (2)C41—C421.375 (2)
C15—H150.9300C41—C461.388 (2)
C16—N41.474 (2)C42—C431.387 (3)
N3—O321.216 (2)C42—H420.9300
N3—O311.220 (2)C43—C441.372 (3)
N4—O411.220 (2)C43—H430.9300
N4—O421.221 (2)C44—C451.363 (3)
N2—C31.3226 (18)C44—H440.9300
C3—C41.423 (2)C45—C461.378 (3)
C3—C311.476 (2)C45—H450.9300
C31—C321.389 (2)C46—H460.9300
C31—C361.391 (2)C5—H50.9300
C32—C331.379 (2)
C5—N1—N2111.59 (11)C34—C33—C32119.89 (16)
C5—N1—C11129.66 (12)C34—C33—H33120.1
N2—N1—C11118.72 (11)C32—C33—H33120.1
C12—C11—C16117.79 (14)C33—C34—C35120.16 (16)
C12—C11—N1118.62 (13)C33—C34—H34119.9
C16—C11—N1123.57 (13)C35—C34—H34119.9
C13—C12—C11120.99 (15)C34—C35—C36120.34 (15)
C13—C12—H12119.5C34—C35—H35119.8
C11—C12—H12119.5C36—C35—H35119.8
C14—C13—C12119.03 (15)C35—C36—C31120.03 (15)
C14—C13—H13120.5C35—C36—H36120.0
C12—C13—H13120.5C31—C36—H36120.0
C15—C14—C13122.07 (15)C5—C4—C3105.46 (12)
C15—C14—N3118.56 (15)C5—C4—S1125.31 (11)
C13—C14—N3119.32 (15)C3—C4—S1129.16 (11)
C14—C15—C16118.29 (15)C4—S1—C41102.81 (7)
C14—C15—H15120.9C42—C41—C46119.70 (17)
C16—C15—H15120.9C42—C41—S1124.36 (13)
C15—C16—C11121.73 (14)C46—C41—S1115.94 (14)
C15—C16—N4114.95 (14)C41—C42—C43119.49 (18)
C11—C16—N4123.04 (14)C41—C42—H42120.3
O32—N3—O31124.40 (16)C43—C42—H42120.3
O32—N3—C14118.10 (16)C44—C43—C42120.7 (2)
O31—N3—C14117.51 (16)C44—C43—H43119.7
O41—N4—O42125.20 (16)C42—C43—H43119.7
O41—N4—C16117.19 (16)C45—C44—C43119.7 (2)
O42—N4—C16117.54 (15)C45—C44—H44120.2
C3—N2—N1104.98 (11)C43—C44—H44120.2
N2—C3—C4110.73 (12)C44—C45—C46120.7 (2)
N2—C3—C31120.64 (12)C44—C45—H45119.7
C4—C3—C31128.63 (13)C46—C45—H45119.7
C32—C31—C36118.85 (14)C45—C46—C41119.8 (2)
C32—C31—C3120.26 (13)C45—C46—H46120.1
C36—C31—C3120.89 (13)C41—C46—H46120.1
C33—C32—C31120.73 (15)N1—C5—C4107.22 (13)
C33—C32—H32119.6N1—C5—H5126.4
C31—C32—H32119.6C4—C5—H5126.4
C5—N1—C11—C12150.11 (15)N2—C3—C31—C3645.2 (2)
N2—N1—C11—C12−27.9 (2)C4—C3—C31—C36−135.11 (16)
C5—N1—C11—C16−28.3 (2)C36—C31—C32—C33−0.6 (2)
N2—N1—C11—C16153.72 (14)C3—C31—C32—C33178.96 (15)
C16—C11—C12—C13−0.9 (2)C31—C32—C33—C340.4 (3)
N1—C11—C12—C13−179.36 (15)C32—C33—C34—C35−0.2 (3)
C11—C12—C13—C142.6 (3)C33—C34—C35—C360.0 (3)
C12—C13—C14—C15−1.5 (3)C34—C35—C36—C31−0.2 (2)
C12—C13—C14—N3−179.20 (15)C32—C31—C36—C350.4 (2)
C13—C14—C15—C16−1.3 (2)C3—C31—C36—C35−179.10 (14)
N3—C14—C15—C16176.38 (14)N2—C3—C4—C5−0.01 (17)
C14—C15—C16—C113.1 (2)C31—C3—C4—C5−179.74 (14)
C14—C15—C16—N4−170.88 (14)N2—C3—C4—S1−176.96 (11)
C12—C11—C16—C15−2.1 (2)C31—C3—C4—S13.3 (2)
N1—C11—C16—C15176.35 (14)C5—C4—S1—C4191.96 (14)
C12—C11—C16—N4171.45 (14)C3—C4—S1—C41−91.65 (15)
N1—C11—C16—N4−10.1 (2)C4—S1—C41—C42−6.10 (16)
C15—C14—N3—O32−165.63 (16)C4—S1—C41—C46174.66 (13)
C13—C14—N3—O3212.1 (2)C46—C41—C42—C430.0 (3)
C15—C14—N3—O3113.8 (2)S1—C41—C42—C43−179.18 (14)
C13—C14—N3—O31−168.44 (17)C41—C42—C43—C440.5 (3)
C15—C16—N4—O41−42.7 (2)C42—C43—C44—C45−0.3 (3)
C11—C16—N4—O41143.32 (16)C43—C44—C45—C46−0.4 (3)
C15—C16—N4—O42134.48 (16)C44—C45—C46—C410.9 (3)
C11—C16—N4—O42−39.4 (2)C42—C41—C46—C45−0.7 (3)
C5—N1—N2—C31.50 (16)S1—C41—C46—C45178.53 (15)
C11—N1—N2—C3179.83 (12)N2—N1—C5—C4−1.54 (17)
N1—N2—C3—C4−0.88 (16)C11—N1—C5—C4−179.63 (14)
N1—N2—C3—C31178.87 (12)C3—C4—C5—N10.92 (16)
N2—C3—C31—C32−134.32 (15)S1—C4—C5—N1178.02 (11)
C4—C3—C31—C3245.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C35—H35···O42i0.932.583.452 (2)157
C5—H5···N2ii0.932.523.411 (2)161
Symmetry codes: (i) x, y, z+1; (ii) x−1/2, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formulaC21H14N4O4S
Mr418.42
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)7.3062 (4), 26.5212 (13), 10.3361 (5)
β (°) 104.012 (1)
V (Å3)1943.22 (17)
Z4
Radiation typeMo Kα
µ (mm−1)0.20
Crystal size (mm)0.24 × 0.21 × 0.18
Data collection
DiffractometerBruker SMART APEX CCD
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		18559, 3426, 3128
Rint0.021
(sin θ/λ)max (Å−1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.091, 1.04
No. of reflections3426
No. of parameters271
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.27, −0.14

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C35—H35···O42i0.932.583.452 (2)157
C5—H5···N2ii0.932.523.411 (2)161
Symmetry codes: (i) x, y, z+1; (ii) x−1/2, −y+1/2, z−1/2.
 

Acknowledgements

VS and SAB sincerely thank the Vice Chancellor and Management of the Kalasalingam University, Anand Nagar, Krishnan Koil, for their support and encouragement.

References

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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.

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ISSN: 2056-9890
Volume 68| Part 10| October 2012| Page o2845
https://doi.org/10.1107/S1600536812036914
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