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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 70| Part 2| February 2014| Pages o219-o220
doi:10.1107/S1600536814001706

Ethyl (4-{[(di­ethyl­carbamo­thio­yl)sulfan­yl]meth­yl}-2-oxo-2H-chromen-7-yl)carbamate

K. R. Roopashree,a K. Mahesh Kumar,b B. R. Anitha,a A. J. Ravia and H. C. Devarajegowdaa*

aDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India, and bDepartment of Chemistry, Karnatak University's Karnatak Science College, Dharwad, Karnataka 580 001, India
*Correspondence e-mail: devarajegowda@yahoo.com

(Received 21 January 2014; accepted 23 January 2014; online 29 January 2014)

In the title compound, C18H22N2O4S2, the 2H-chromene ring system is essentially planar (r.m.s. deviation = 0.012 Å). The mol­ecular conformation is stabilized by a C—H⋯O hydrogen bond. In the crystal, N—H⋯S and C—H⋯O hydrogen bonds occur, the former enclosing an R22(22) ring motif, and lead to the formation of a two-dimensional slab-like network lying parallel to (10-1). π–π inter­actions are observed between inversion-related aromatic rings [shortest centroid–centroid distance = 3.6300 (11) Å].

CCDC reference: 983180

Related literature

For biological applications of coumarins and di­thio­carbamates, see: Cao et al. (2005[Cao, S.-L., Feng, Y.-P., Jiang, Y.-Y., Liu, S.-Y., Ding, G.-Y. & Li, R.-T. (2005). Bioorg. Med. Chem. Lett. 15, 1915-1917.]); Chen et al. (2008[Chen, X., She, J., Shang, Z. C., Wu, J. & Zhang, P. Z. (2008). Synthesis, 24, 3931-3936.]); Gerhauser et al. (1997[Gerhauser, C., You, M., Liu, J., Moriarty, R. M., Hawthorne, M., Mehta, R. G., Moon, R. C. & Pezzuto, J. M. (1997). Cancer Res. 57, 272-278.]); Mehta et al. (1995[Mehta, G. R., Liu, J., Constantinou, A., Thomas, F. C., Hawthorne, M., You, M., Gerhauser, C., Pezzuto, M. J., Moon, C. R. & Moriarty, M. R. (1995). Carcinogenesis, 16, 399-404.]); Valizadeha & Shockravi (2005[Valizadeha, H. & Shockravi, A. (2005). Tetrahedron Lett. 46, 3501-3503.]); Zhang et al. (2005[Zhang, D., Chen, J., Liang, Y. & Zhou, H. (2005). Synth. Commun. 35, 521-526.]). For a related structure with comparable bond lengths and for the synthesis, see: Kumar et al. (2012[Kumar, K. M., Devarajegowda, H. C., Jeyaseelan, S., Mahabaleshwaraiah, N. M. & Kotresh, O. (2012). Acta Cryst. E68, o1657.]).

[Scheme 1]

Experimental

Crystal data

  • C18H22N2O4S2

  • Mr = 394.50

  • Triclinic, [P \overline 1]

  • a = 8.0573 (3) Å

  • b = 9.0358 (4) Å

  • c = 14.2400 (6) Å

  • α = 74.137 (3)°

  • β = 87.831 (3)°

  • γ = 73.320 (2)°

  • V = 954.36 (7) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.31 mm−1

  • T = 296 K

  • 0.24 × 0.20 × 0.12 mm
Data collection

  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2007[Sheldrick, G. M. (2007). SADABS. University of Göttingen, Germany.]) Tmin = 0.770, Tmax = 1.000

  • 14877 measured reflections

  • 3305 independent reflections

  • 2808 reflections with I > 2σ(I)

  • Rint = 0.031
Refinement

  • R[F2 > 2σ(F2)] = 0.035

  • wR(F2) = 0.101

  • S = 0.95

  • 3305 reflections

  • 235 parameters

  • H-atom parameters constrained

  • Δρmax = 0.25 e Å−3

  • Δρmin = −0.17 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N7—H7⋯S2i 0.86 2.63 3.4858 (17) 172
C17—H17⋯O4 0.93 2.28 2.876 (2) 121
C25—H25B⋯O6ii 0.97 2.49 3.306 (3) 142
Symmetry codes: (i) -x+1, -y+2, -z; (ii) -x+2, -y+1, -z+1.

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc.,Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART 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 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 983180

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536814001706/bt6958sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814001706/bt6958Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814001706/bt6958Isup3.cml

checkCIF report


Comment top

Coumarin and its derivatives are an important class of heterocyclic compound and a number of preparations have been known since late 19th century. Various compounds possessing an azomethine linkage at C-7 have been synthesized and evaluated for their anti-oxidant ability and anti-inflammatory activity. They showed 58% and 54% inhibition of inflammation induced by Carrageenan, which was better than the standard indomethacin (Valizadeha et al., 2005). The luminescent property of Europium chelates of acylated 7-amino coumarins has been used to label proteins at cysteine residues on synthetic oligonucleotides containing a free thiol group (Chen et al., 2008).

Organic dithiocarbamates have attracted a great deal of interest due to their interesting chemistry and wide utility (Zhang et al., 2005). Dithiocarbamates have a wide range of uses and applications and are produced in great quantities throughout the world. Since, brassinin (Mehta et al., 1995) a crucial plant defense first isolated from cabbage, had cancer preventive activity, structural modification on this compound led to the synthesis of sulforamate (Gerhauser et al., 1997) and a series of dithiocarbamates, some of which were found to have in-vitro and in-vivo antitumor activity (Cao et al., 2005). A steadily increasing number of structural studies have been published from our research group on dithiocarbamates. Based on the above literature survey we synthesized the title molecule for its chemical and physical studies.

The asymmetric unit of Ethyl (4-{[(diethylcarbamothioyl)thio]methyl} -2-oxo-2H-chromen-7-yl)carbamate is shown in Fig. 1. The 2H -chromene ring system is nearly planar, with a maximum deviation of 0.0149 (18) Å for the atom C13. The molecular conformation is stabilized by a C-H···O hydrogen bond and the crystal packing is stabilized by N—H···S and C–H···O hydrogen bonds (Table 1). The N—H···S hydrogen bonds form an R2 2(22) ring pattern. In addition, π–π interactions between inversion related molecules are also observed: Cg1···Cg2iii 3.6300 (11) Å [Cg1 is the centroid of the ring formed by C12 to C17, Cg2 is the centroid of the ring formed by O5,C15,C16,C18,C19,C20; symmetry operator (iii): -x+2, -y+2, -z] (Fig. 2).

Related literature top

For biological applications of coumarins and dithiocarbamates, see: Cao et al. (2005); Chen et al. (2008); Gerhauser et al. (1997); Mehta et al. (1995); Valizadeha & Shockravi (2005); Zhang et al. (2005). For a related structure with comparable bond lengths and for the synthesis, see: Kumar et al. (2012).

Experimental top

All the chemicals used were of analytical reagent grade and were used directly without further purification. The title compound was synthesized according to the reported method7 (Kumar et al., 2012). The compound is recrystallized by ethanol-chloroform mixture. Colourless needles of the title compound were grown from a mixed solution of Ethanol/Chloroform (V/V = 2/1) by slow evaporation at room temperature. Yield= 91%, m.p. 445 K.

Refinement top

All H atoms were positioned geometrically, with N—H = 0.86 Å, C—H = 0.93 Å for aromatic H, C—H = 0.97 Å for methylene H and C—H = 0.96 Å for methyl H and were refined using a riding model with Uiso(H) = 1.5Ueq(C) for methyl H and Uiso(H) = 1.2Ueq(C,N) for all other H.

Structure description top

Coumarin and its derivatives are an important class of heterocyclic compound and a number of preparations have been known since late 19th century. Various compounds possessing an azomethine linkage at C-7 have been synthesized and evaluated for their anti-oxidant ability and anti-inflammatory activity. They showed 58% and 54% inhibition of inflammation induced by Carrageenan, which was better than the standard indomethacin (Valizadeha et al., 2005). The luminescent property of Europium chelates of acylated 7-amino coumarins has been used to label proteins at cysteine residues on synthetic oligonucleotides containing a free thiol group (Chen et al., 2008).

Organic dithiocarbamates have attracted a great deal of interest due to their interesting chemistry and wide utility (Zhang et al., 2005). Dithiocarbamates have a wide range of uses and applications and are produced in great quantities throughout the world. Since, brassinin (Mehta et al., 1995) a crucial plant defense first isolated from cabbage, had cancer preventive activity, structural modification on this compound led to the synthesis of sulforamate (Gerhauser et al., 1997) and a series of dithiocarbamates, some of which were found to have in-vitro and in-vivo antitumor activity (Cao et al., 2005). A steadily increasing number of structural studies have been published from our research group on dithiocarbamates. Based on the above literature survey we synthesized the title molecule for its chemical and physical studies.

The asymmetric unit of Ethyl (4-{[(diethylcarbamothioyl)thio]methyl} -2-oxo-2H-chromen-7-yl)carbamate is shown in Fig. 1. The 2H -chromene ring system is nearly planar, with a maximum deviation of 0.0149 (18) Å for the atom C13. The molecular conformation is stabilized by a C-H···O hydrogen bond and the crystal packing is stabilized by N—H···S and C–H···O hydrogen bonds (Table 1). The N—H···S hydrogen bonds form an R2 2(22) ring pattern. In addition, π–π interactions between inversion related molecules are also observed: Cg1···Cg2iii 3.6300 (11) Å [Cg1 is the centroid of the ring formed by C12 to C17, Cg2 is the centroid of the ring formed by O5,C15,C16,C18,C19,C20; symmetry operator (iii): -x+2, -y+2, -z] (Fig. 2).

For biological applications of coumarins and dithiocarbamates, see: Cao et al. (2005); Chen et al. (2008); Gerhauser et al. (1997); Mehta et al. (1995); Valizadeha & Shockravi (2005); Zhang et al. (2005). For a related structure with comparable bond lengths and for the synthesis, see: Kumar et al. (2012).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are shown as spheres of arbitrary radius.
[Figure 2] Fig. 2. The crystal packing of the title compound. N-H···S hydrogen bonds are drawn as dashed lines
Ethyl (4-{[(diethylcarbamothioyl)sulfanyl]methyl}-2-oxo-2H-chromen-7-yl)carbamate top
Crystal data top
C18H22N2O4S2Z = 2
Mr = 394.50F(000) = 416
Triclinic, P1Dx = 1.373 Mg m−3
Hall symbol: -P 1Melting point: 445 K
a = 8.0573 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.0358 (4) ÅCell parameters from 3305 reflections
c = 14.2400 (6) Åθ = 1.5–25.0°
α = 74.137 (3)°µ = 0.31 mm−1
β = 87.831 (3)°T = 296 K
γ = 73.320 (2)°Plate, colourless
V = 954.36 (7) Å30.24 × 0.20 × 0.12 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		3305 independent reflections
Radiation source: fine-focus sealed tube2808 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
ω and φ scansθmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2007)		h = −9→9
Tmin = 0.770, Tmax = 1.000k = −10→10
14877 measured reflectionsl = −16→16
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) = 0.101H-atom parameters constrained
S = 0.95 w = 1/[σ2(Fo2) + (0.0672P)2 + 0.1652P]
where P = (Fo2 + 2Fc2)/3
3305 reflections(Δ/σ)max < 0.001
235 parametersΔρmax = 0.25 e Å−3
0 restraintsΔρmin = −0.17 e Å−3
Crystal data top
C18H22N2O4S2γ = 73.320 (2)°
Mr = 394.50V = 954.36 (7) Å3
Triclinic, P1Z = 2
a = 8.0573 (3) ÅMo Kα radiation
b = 9.0358 (4) ŵ = 0.31 mm−1
c = 14.2400 (6) ÅT = 296 K
α = 74.137 (3)°0.24 × 0.20 × 0.12 mm
β = 87.831 (3)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		3305 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2007)		2808 reflections with I > 2σ(I)
Tmin = 0.770, Tmax = 1.000Rint = 0.031
14877 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0350 restraints
wR(F2) = 0.101H-atom parameters constrained
S = 0.95Δρmax = 0.25 e Å−3
3305 reflectionsΔρmin = −0.17 e Å−3
235 parameters
Special details top

Experimental. IR (KBr, cm-1): 1000, 1152, 1227, 1422, 1501, 1695, 1720, 3265. GCMS: m/e: 384. 1H NMR (400 MHz, CDCl3, δ,. p.p.m): 7.68 (dd, 1H, Ar—H), 7.36 (d, 1H, Ar—H), 7.26 (s, 1H, Ar—H), 6.91 (s, 1H, NH), 6.46 (s, 2H, Ar—H), 4.71 (s, 2H, CH2), 4.29 (q, 2H, CH2), 4.06 (q, 2H, CH2), 3.78 (q, 2H, CH2), 1.59 (s, 3H, CH3), 1.35 (m, 6H, CH3). Mol. Formula: C18H22N2O4S2. Elemental analysis: C, 54.80; H, 5.62; N, 7.10 (calculated); C, 54.84; H, 5.58; N, 7.14 (found).

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 > 2σ(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
S10.95674 (6)0.46925 (5)0.22606 (3)0.04992 (16)
S20.60616 (6)0.62085 (5)0.29583 (3)0.05289 (16)
O30.57157 (17)1.67152 (13)−0.18754 (9)0.0517 (3)
O50.95552 (18)1.08031 (13)0.18541 (8)0.0512 (3)
O40.7317 (2)1.58432 (15)−0.04675 (10)0.0616 (4)
O61.1139 (3)0.93665 (17)0.31862 (11)0.0900 (6)
N70.6313 (2)1.41614 (16)−0.10823 (10)0.0480 (4)
H70.56821.4173−0.15590.058*
N80.84521 (18)0.36613 (16)0.39956 (10)0.0431 (3)
C90.4882 (4)1.9375 (2)−0.28981 (17)0.0794 (7)
H9A0.49192.0456−0.29830.119*
H9B0.36971.9354−0.28850.119*
H9C0.54311.8991−0.34310.119*
C100.5810 (3)1.8330 (2)−0.19639 (14)0.0562 (5)
H10A0.70101.8343−0.19670.067*
H10B0.52671.8705−0.14190.067*
C110.6522 (2)1.55978 (19)−0.10780 (12)0.0441 (4)
C120.6996 (2)1.26657 (19)−0.04079 (11)0.0404 (4)
C130.6722 (2)1.1326 (2)−0.06140 (12)0.0440 (4)
H130.60911.1460−0.11800.053*
C140.7369 (2)0.98170 (19)0.00062 (11)0.0413 (4)
H140.71640.8944−0.01430.050*
C150.8334 (2)0.95701 (18)0.08610 (11)0.0381 (4)
C160.8600 (2)1.09192 (19)0.10417 (11)0.0397 (4)
C170.7951 (2)1.24599 (19)0.04376 (11)0.0427 (4)
H170.81471.33340.05910.051*
C180.9075 (2)0.80158 (19)0.15570 (11)0.0399 (4)
C191.0006 (3)0.7950 (2)0.23349 (12)0.0507 (5)
H191.04830.69560.27800.061*
C201.0302 (3)0.9345 (2)0.25129 (13)0.0564 (5)
C210.8756 (3)0.65683 (19)0.13488 (12)0.0466 (4)
H21A0.92740.64570.07360.056*
H21B0.75150.67750.12570.056*
C220.7977 (2)0.47977 (18)0.31595 (11)0.0400 (4)
C231.0135 (3)0.2415 (2)0.41870 (15)0.0568 (5)
H23A1.05810.22350.35730.068*
H23B0.99720.14170.45920.068*
C241.1436 (3)0.2872 (4)0.4689 (2)0.0881 (8)
H24A1.25130.20300.47980.132*
H24B1.10110.30290.53040.132*
H24C1.16190.38490.42850.132*
C250.7274 (2)0.3530 (2)0.48079 (12)0.0513 (4)
H25A0.65370.45940.47970.062*
H25B0.79500.30900.54220.062*
C260.6168 (3)0.2487 (3)0.47493 (17)0.0731 (6)
H26A0.54190.24290.52910.110*
H26B0.68930.14280.47710.110*
H26C0.54800.29310.41480.110*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0656 (3)0.0310 (2)0.0483 (3)−0.0110 (2)0.0094 (2)−0.00698 (18)
S20.0549 (3)0.0449 (3)0.0458 (3)0.0002 (2)−0.0096 (2)−0.0051 (2)
O30.0703 (9)0.0313 (6)0.0473 (7)−0.0103 (6)−0.0114 (6)−0.0034 (5)
O50.0787 (9)0.0340 (6)0.0398 (6)−0.0181 (6)−0.0181 (6)−0.0036 (5)
O40.0918 (10)0.0410 (7)0.0514 (8)−0.0213 (7)−0.0214 (7)−0.0062 (6)
O60.1509 (16)0.0488 (8)0.0661 (10)−0.0303 (9)−0.0594 (10)0.0009 (7)
N70.0632 (10)0.0345 (7)0.0423 (8)−0.0139 (7)−0.0147 (7)−0.0021 (6)
N80.0500 (8)0.0322 (7)0.0402 (7)−0.0088 (6)−0.0049 (6)−0.0013 (6)
C90.127 (2)0.0356 (10)0.0623 (13)−0.0109 (12)−0.0103 (13)−0.0040 (9)
C100.0799 (14)0.0318 (9)0.0540 (11)−0.0136 (9)−0.0023 (9)−0.0088 (8)
C110.0536 (10)0.0334 (9)0.0388 (9)−0.0076 (7)−0.0026 (8)−0.0040 (7)
C120.0464 (9)0.0345 (8)0.0364 (8)−0.0117 (7)−0.0014 (7)−0.0031 (7)
C130.0530 (10)0.0420 (9)0.0367 (8)−0.0169 (8)−0.0083 (7)−0.0054 (7)
C140.0535 (10)0.0355 (8)0.0382 (8)−0.0192 (7)−0.0010 (7)−0.0086 (7)
C150.0473 (9)0.0339 (8)0.0323 (8)−0.0138 (7)0.0020 (7)−0.0055 (6)
C160.0519 (10)0.0357 (8)0.0318 (8)−0.0149 (7)−0.0038 (7)−0.0064 (6)
C170.0576 (11)0.0322 (8)0.0384 (9)−0.0155 (7)−0.0049 (7)−0.0064 (7)
C180.0536 (10)0.0336 (8)0.0316 (8)−0.0152 (7)0.0029 (7)−0.0045 (6)
C190.0743 (13)0.0349 (9)0.0381 (9)−0.0152 (8)−0.0093 (8)−0.0011 (7)
C200.0847 (14)0.0385 (9)0.0422 (10)−0.0184 (9)−0.0198 (9)−0.0014 (7)
C210.0703 (12)0.0351 (9)0.0348 (8)−0.0203 (8)0.0020 (8)−0.0049 (7)
C220.0526 (10)0.0294 (8)0.0389 (8)−0.0146 (7)−0.0049 (7)−0.0072 (6)
C230.0605 (12)0.0352 (9)0.0592 (11)−0.0020 (8)−0.0052 (9)0.0009 (8)
C240.0551 (14)0.0930 (18)0.104 (2)−0.0066 (13)−0.0218 (13)−0.0188 (15)
C250.0603 (12)0.0476 (10)0.0392 (9)−0.0146 (9)−0.0036 (8)−0.0010 (7)
C260.0832 (16)0.0737 (15)0.0689 (14)−0.0414 (13)0.0086 (12)−0.0107 (11)
Geometric parameters (Å, º) top
S1—C221.7781 (17)C14—C151.400 (2)
S1—C211.7920 (16)C14—H140.9300
S2—C221.6714 (17)C15—C161.387 (2)
O3—C111.335 (2)C15—C181.454 (2)
O3—C101.454 (2)C16—C171.383 (2)
O5—C201.375 (2)C17—H170.9300
O5—C161.377 (2)C18—C191.340 (3)
O4—C111.202 (2)C18—C211.509 (2)
O6—C201.201 (2)C19—C201.436 (3)
N7—C111.357 (2)C19—H190.9300
N7—C121.398 (2)C21—H21A0.9700
N7—H70.8600C21—H21B0.9700
N8—C221.326 (2)C23—C241.498 (3)
N8—C251.470 (2)C23—H23A0.9700
N8—C231.471 (2)C23—H23B0.9700
C9—C101.484 (3)C24—H24A0.9600
C9—H9A0.9600C24—H24B0.9600
C9—H9B0.9600C24—H24C0.9600
C9—H9C0.9600C25—C261.490 (3)
C10—H10A0.9700C25—H25A0.9700
C10—H10B0.9700C25—H25B0.9700
C12—C171.394 (2)C26—H26A0.9600
C12—C131.398 (2)C26—H26B0.9600
C13—C141.371 (2)C26—H26C0.9600
C13—H130.9300
C22—S1—C21102.94 (8)C19—C18—C15118.47 (15)
C11—O3—C10115.29 (14)C19—C18—C21124.04 (15)
C20—O5—C16121.44 (13)C15—C18—C21117.48 (14)
C11—N7—C12128.10 (15)C18—C19—C20122.95 (16)
C11—N7—H7115.9C18—C19—H19118.5
C12—N7—H7115.9C20—C19—H19118.5
C22—N8—C25121.32 (14)O6—C20—O5116.39 (16)
C22—N8—C23124.24 (15)O6—C20—C19126.28 (17)
C25—N8—C23114.42 (14)O5—C20—C19117.33 (15)
C10—C9—H9A109.5C18—C21—S1116.27 (12)
C10—C9—H9B109.5C18—C21—H21A108.2
H9A—C9—H9B109.5S1—C21—H21A108.2
C10—C9—H9C109.5C18—C21—H21B108.2
H9A—C9—H9C109.5S1—C21—H21B108.2
H9B—C9—H9C109.5H21A—C21—H21B107.4
O3—C10—C9107.06 (16)N8—C22—S2123.52 (13)
O3—C10—H10A110.3N8—C22—S1113.94 (13)
C9—C10—H10A110.3S2—C22—S1122.55 (9)
O3—C10—H10B110.3N8—C23—C24112.18 (18)
C9—C10—H10B110.3N8—C23—H23A109.2
H10A—C10—H10B108.6C24—C23—H23A109.2
O4—C11—O3124.67 (15)N8—C23—H23B109.2
O4—C11—N7126.25 (15)C24—C23—H23B109.2
O3—C11—N7109.07 (15)H23A—C23—H23B107.9
C17—C12—N7123.04 (15)C23—C24—H24A109.5
C17—C12—C13119.40 (15)C23—C24—H24B109.5
N7—C12—C13117.55 (15)H24A—C24—H24B109.5
C14—C13—C12120.94 (15)C23—C24—H24C109.5
C14—C13—H13119.5H24A—C24—H24C109.5
C12—C13—H13119.5H24B—C24—H24C109.5
C13—C14—C15121.05 (15)N8—C25—C26111.89 (16)
C13—C14—H14119.5N8—C25—H25A109.2
C15—C14—H14119.5C26—C25—H25A109.2
C16—C15—C14116.74 (14)N8—C25—H25B109.2
C16—C15—C18118.47 (15)C26—C25—H25B109.2
C14—C15—C18124.79 (15)H25A—C25—H25B107.9
O5—C16—C17114.95 (14)C25—C26—H26A109.5
O5—C16—C15121.31 (14)C25—C26—H26B109.5
C17—C16—C15123.74 (15)H26A—C26—H26B109.5
C16—C17—C12118.13 (15)C25—C26—H26C109.5
C16—C17—H17120.9H26A—C26—H26C109.5
C12—C17—H17120.9H26B—C26—H26C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N7—H7···S2i0.862.633.4858 (17)172
C17—H17···O40.932.282.876 (2)121
C25—H25B···O6ii0.972.493.306 (3)142
Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+2, −y+1, −z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N7—H7···S2i0.862.633.4858 (17)172.00
C17—H17···O40.932.282.876 (2)121.00
C25—H25B···O6ii0.972.493.306 (3)142.00
Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+2, −y+1, −z+1.
 

Acknowledgements

The authors thank the Universities Sophisticated Instrumental Centre, Karnatak University, Dharwad, for the CCD X-ray facilities, X-ray data collection, GCMS, IR, CHNS and NMR data. KMK is grateful to Karnatak Science College, Dharwad, for providing laboratory facilities.

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ISSN: 2056-9890
Volume 70| Part 2| February 2014| Pages o219-o220
doi:10.1107/S1600536814001706
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