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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 6| June 2013| Pages o857-o858

6′-(1,3-Di­phenyl-1H-pyrazol-4-yl)-7′-(1H-indol-3-ylcarbon­yl)-2-oxo-1-(prop-2-en-1-yl)-5′,6′,7′,7a'-tetra­hydro-1′H-spiro­[indoline-3,5′-pyrrolo­[1,2-c][1,3]thia­zole]-7′-carbo­nitrile

aDepartment of Physics, S.M.K. Fomra Institute of Technology, Thaiyur, Chennai 603 103, India, bIndustrial Chemistry Laboratory, Central Leather Research Institute, Adyar, Chennai 600 020, India, and cDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India
*Correspondence e-mail: a_sp59@yahoo.in

(Received 10 April 2013; accepted 27 April 2013; online 11 May 2013)

In the title compound, C41H32N6O2S, the pyrrolo­thia­zole ring system is folded about the bridging N—C bond. The thia­zolidine and pyrrolidine rings adopt envelope (with the fused C atom as the flap) and twisted conformations, respectively. The two phenyl rings attached to the pyrazole ring are twisted from the plane of the latter by 6.8 (1) and 52.8 (1)°. The allyl group is disordered over two conformations in a 0.805 (6):0.195 (6) ratio. In the crystal, pairs of N—H⋯O hydrogen bonds link the mol­ecules into centrosymmetric dimers.

Related literature

For the biological activity of spiro­heterocycles, see: Kilonda et al. (1995[Kilonda, A., Compernolle, F. & Hoornaert, G. J. (1995). J. Org. Chem. 60, 5820-5824.]); Ferguson et al. (2005[Ferguson, N. M., Cummings, D. A. T., Cauchemez, S., Fraser, C., Riley, S., Meeyai, A., Iamsirithaworn, S. & Burke, D. S. (2005). Nature (London), 437, 209-214.]). For related structures, see: Jagadeesan et al. (2012a[Jagadeesan, G., Sethusankar, K., Prasanna, R. & Raghunathan, R. (2012a). Acta Cryst. E68, o382-o383.],b[Jagadeesan, G., Sethusankar, K., Prasanna, R. & Raghunathan, R. (2012b). Acta Cryst. E68, o2505-o2506.]). For ring conformations, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C41H32N6O2S

  • Mr = 672.80

  • Monoclinic, P 21 /n

  • a = 10.7396 (10) Å

  • b = 16.3471 (14) Å

  • c = 20.112 (2) Å

  • β = 105.485 (4)°

  • V = 3402.7 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.14 mm−1

  • T = 293 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker SMART APEXII area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker. (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.958, Tmax = 0.972

  • 25634 measured reflections

  • 5983 independent reflections

  • 3281 reflections with I > 2σ(I)

  • Rint = 0.049

Refinement
  • R[F2 > 2σ(F2)] = 0.049

  • wR(F2) = 0.146

  • S = 1.06

  • 5983 reflections

  • 483 parameters

  • 48 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.40 e Å−3

  • Δρmin = −0.30 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N5—H5A⋯O1i 0.92 (4) 1.92 (4) 2.822 (4) 166 (3)
Symmetry code: (i) -x, -y, -z+1.

Data collection: APEX2 (Bruker, 2008[Bruker. (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker. (2008). APEX2, SAINT and SADABS. 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 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

The design and synthesis of glycospiroheterocycles are important in view of their biological profile against viruses, bacteria, and cancer cells (Ferguson et al., 2005). Pyrrolidines and pyrroles are common structural motifs in drugs and drug candidates owing to their ability to act as selective glycosidase inhibitors, which are used in the treatment of diabetes, cancer, malaria and viral infections, including AIDS (Kilonda et al., 1995). Herewith we present the title compound (I), obtained in our group and containing glycospiroheterocycles.

In (I) (Fig. 1), the indole ring system(C1-C8/N6) is essentially planar (r.m.s.deviation = -0.064 Å ). The pyrollidine ring C8/C11-C13/N1) forms dihedral angle of 60.3 (1) with thiazole ring (C9-C11/N1/S1). The thiazole ring adopts an envelope conformation on C11 atom, with the puckering parameters of q2 = 0.363 (3) Å, ϕ = 285.6 (5)° (Cremer & Pople, 1975). The pyrollidine ring adopts twisted conformation on C11-C12 atom, with the puckering parameters of q2 = 0.367 (3) Å, ϕ = 301.1 (5)°. The allyl group is disordered over two conformations in a ratio 0.805 (6):0.195 (6). The crystal packing features are intermolecular N—H···O hydrogen bonds (Table 1), which link the molecules into centrosymmetric dimers.

Related literature top

For the biological activity of spiroheterocycles, see: Kilonda et al. (1995); Ferguson et al. (2005). For related structures, see: Jagadeesan et al. (2012a,b). For ring conformations, see: Cremer & Pople (1975).

Experimental top

A mixture of allyl Isatin (1 mmol), thiaproline(1.1 mmol) and (2E)-3-(1,3- diphenyl-1H-pyrazol-4-yl)-2-[(E)-(1H-indol-3-yl) carbonyl] prop-2-enenitrile (1.3 mmol) were refluxed in ethanol (5 mL) for about 3 h. Completion of the reaction was evidenced by TLC analysis. After completion of the reaction, the reaction mixture was poured into ice-water, the resulting solid was filtered off and purified by column chromatography using ethyl acetate/Ether (6:4) as an eluent to afford pure spirooxindole.The block shaped single crystals of the title compound suitable for X-ray diffraction were obtained from solution of ethyl acetate/Ether (6:4) by slow evaportion at room temperature.

Refinement top

Amino H atom was located on difference map and isotropically refined. C-bound H atoms were positioned geometrically, with C—H = 0.93 - 0.98 Å, and allowed to ride on their parent atoms, with Uiso(H) = 1.2–1.5 Ueq(C). The positions of methyl hydrogens were optimized rotationally.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing the atomic numbering and 30% probabilty displacement ellipsoids. For the disordered allyl group, only major part is shown.
6'-(1,3-Diphenyl-1H-pyrazol-4-yl)-7'-(1H-indol-3-ylcarbonyl)-2-oxo-1-(prop-2-en-1-yl)-5',6',7',7a'-tetrahydro-1'H-spiro[indoline-3,5'-pyrrolo[1,2-c][1,3]thiazole]-7'-carbonitrile top
Crystal data top
C41H32N6O2SF(000) = 1408
Mr = 672.80Dx = 1.313 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 5983 reflections
a = 10.7396 (10) Åθ = 1.6–25.0°
b = 16.3471 (14) ŵ = 0.14 mm1
c = 20.112 (2) ÅT = 293 K
β = 105.485 (4)°Block, colourless
V = 3402.7 (6) Å30.30 × 0.25 × 0.20 mm
Z = 4
Data collection top
Bruker SMART APEXII area-detector
diffractometer
5983 independent reflections
Radiation source: fine-focus sealed tube3281 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.049
ω and ϕ scansθmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
h = 1212
Tmin = 0.958, Tmax = 0.972k = 1919
25634 measured reflectionsl = 2323
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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0428P)2 + 2.1778P]
where P = (Fo2 + 2Fc2)/3
5983 reflections(Δ/σ)max < 0.001
483 parametersΔρmax = 0.40 e Å3
48 restraintsΔρmin = 0.30 e Å3
Crystal data top
C41H32N6O2SV = 3402.7 (6) Å3
Mr = 672.80Z = 4
Monoclinic, P21/nMo Kα radiation
a = 10.7396 (10) ŵ = 0.14 mm1
b = 16.3471 (14) ÅT = 293 K
c = 20.112 (2) Å0.30 × 0.25 × 0.20 mm
β = 105.485 (4)°
Data collection top
Bruker SMART APEXII area-detector
diffractometer
5983 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
3281 reflections with I > 2σ(I)
Tmin = 0.958, Tmax = 0.972Rint = 0.049
25634 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04948 restraints
wR(F2) = 0.146H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.40 e Å3
5983 reflectionsΔρmin = 0.30 e Å3
483 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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*/UeqOcc. (<1)
C10.4320 (3)0.18987 (19)0.66619 (17)0.0547 (8)
C20.5399 (4)0.1990 (2)0.6438 (2)0.0728 (11)
H20.54750.17180.60450.087*
C30.6388 (4)0.2494 (3)0.6804 (3)0.0938 (14)
H30.71280.25610.66530.113*
C40.6281 (5)0.2889 (3)0.7378 (3)0.0995 (15)
H40.69570.32210.76170.119*
C50.5211 (4)0.2813 (3)0.7615 (2)0.0883 (13)
H50.51410.30870.80090.106*
C60.4237 (4)0.2312 (2)0.72452 (19)0.0652 (10)
C70.2358 (3)0.1605 (2)0.69221 (17)0.0563 (9)
C80.3155 (3)0.13548 (19)0.64258 (15)0.0486 (8)
C90.2343 (4)0.2121 (2)0.53083 (18)0.0754 (11)
H10A0.27920.25630.55970.090*
H10B0.14720.23010.50840.090*
C100.3350 (3)0.0798 (2)0.49222 (17)0.0665 (10)
H11A0.31730.04400.45230.080*
H11B0.42140.06870.52090.080*
C110.2359 (3)0.06800 (19)0.53247 (14)0.0497 (8)
H120.15100.05830.50030.060*
C120.2648 (3)0.00061 (18)0.58780 (14)0.0444 (7)
C130.3580 (3)0.04386 (17)0.64941 (13)0.0435 (7)
H140.44310.04240.64020.052*
C140.3774 (3)0.00947 (18)0.72085 (14)0.0458 (7)
C150.2870 (3)0.01129 (19)0.75412 (15)0.0507 (8)
H160.19810.01290.73480.061*
C160.4967 (3)0.00417 (19)0.77203 (15)0.0474 (8)
C170.2943 (3)0.04999 (18)0.87456 (15)0.0488 (8)
C180.1634 (3)0.0618 (2)0.86197 (17)0.0664 (10)
H190.11060.05850.81710.080*
C190.1106 (4)0.0784 (2)0.9156 (2)0.0737 (11)
H200.02190.08610.90700.088*
C200.1878 (4)0.0837 (2)0.98147 (19)0.0699 (10)
H210.15200.09461.01790.084*
C210.3172 (4)0.0731 (2)0.99347 (17)0.0690 (10)
H220.36980.07701.03830.083*
C220.3720 (3)0.0566 (2)0.94067 (15)0.0583 (9)
H230.46090.04990.94960.070*
C230.6270 (3)0.0243 (2)0.76733 (16)0.0555 (9)
C240.7013 (4)0.0793 (3)0.81318 (19)0.0784 (11)
H250.66910.10220.84750.094*
C250.8227 (4)0.1005 (3)0.8086 (2)0.0993 (15)
H260.87190.13770.83980.119*
C260.8714 (4)0.0672 (3)0.7582 (3)0.0971 (15)
H270.95360.08150.75520.117*
C270.7988 (4)0.0127 (3)0.7123 (2)0.0863 (13)
H280.83140.00960.67780.104*
C280.6776 (3)0.0092 (2)0.71694 (18)0.0686 (10)
H290.62920.04680.68590.082*
C290.3280 (3)0.07809 (19)0.56533 (15)0.0512 (8)
C300.2501 (3)0.12852 (19)0.51135 (16)0.0517 (8)
C310.1356 (3)0.1070 (2)0.46489 (17)0.0636 (9)
H320.09760.05560.46230.076*
C320.2721 (3)0.21251 (19)0.49676 (16)0.0519 (8)
C330.3645 (3)0.2707 (2)0.5256 (2)0.0683 (10)
H380.43610.25700.56140.082*
C340.3477 (4)0.3495 (2)0.5000 (3)0.0857 (12)
H370.40910.38910.51900.103*
C350.2419 (5)0.3710 (3)0.4468 (3)0.0896 (13)
H360.23360.42470.43120.108*
C360.1504 (4)0.3159 (2)0.4171 (2)0.0781 (11)
H350.07990.33040.38090.094*
C370.1658 (3)0.2367 (2)0.44285 (18)0.0609 (9)
C380.1446 (3)0.02590 (19)0.60293 (14)0.0464 (8)
N10.2303 (2)0.14115 (16)0.57223 (13)0.0539 (7)
N20.0520 (3)0.04893 (18)0.61364 (14)0.0620 (8)
N30.3494 (2)0.02919 (15)0.82025 (12)0.0496 (6)
N40.4784 (2)0.01928 (16)0.83205 (12)0.0532 (7)
N50.0868 (3)0.1700 (2)0.42411 (16)0.0692 (9)
N60.3063 (3)0.2139 (2)0.73847 (15)0.0736 (9)
O10.1263 (2)0.13763 (15)0.68978 (12)0.0691 (7)
O20.4379 (2)0.09462 (15)0.59576 (13)0.0772 (8)
S10.31860 (13)0.18539 (7)0.46628 (6)0.0945 (4)
C390.2629 (10)0.2521 (5)0.7937 (4)0.107 (3)0.805 (6)
H39A0.16930.25190.78250.128*0.805 (6)
H39B0.29250.30840.79990.128*0.805 (6)
C400.3168 (9)0.2052 (6)0.8568 (3)0.152 (4)0.805 (6)
H400.25490.16750.86170.183*0.805 (6)
C410.4063 (9)0.1972 (8)0.9026 (6)0.229 (6)0.805 (6)
H41A0.47840.23010.90630.275*0.805 (6)
H41B0.40660.15780.93600.275*0.805 (6)
C39'0.263 (5)0.227 (3)0.8005 (14)0.125 (8)0.195 (6)
H39C0.33370.24560.83810.150*0.195 (6)
H39D0.22940.17630.81430.150*0.195 (6)
C40'0.161 (3)0.2890 (18)0.7835 (14)0.113 (7)0.195 (6)
H40'0.19310.34080.77900.136*0.195 (6)
C41'0.035 (3)0.2896 (15)0.7732 (13)0.119 (9)0.195 (6)
H41C0.00860.24130.77630.143*0.195 (6)
H41D0.01040.33840.76270.143*0.195 (6)
H5A0.010 (4)0.166 (2)0.390 (2)0.103 (15)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.054 (2)0.049 (2)0.059 (2)0.0032 (16)0.0118 (17)0.0035 (17)
C20.072 (3)0.072 (3)0.074 (2)0.016 (2)0.019 (2)0.005 (2)
C30.077 (3)0.094 (3)0.108 (4)0.031 (3)0.021 (3)0.008 (3)
C40.080 (3)0.083 (3)0.123 (4)0.029 (3)0.006 (3)0.013 (3)
C50.084 (3)0.076 (3)0.094 (3)0.008 (2)0.006 (3)0.024 (2)
C60.058 (2)0.057 (2)0.073 (2)0.0010 (18)0.0041 (19)0.011 (2)
C70.050 (2)0.061 (2)0.054 (2)0.0093 (18)0.0082 (17)0.0019 (17)
C80.0474 (18)0.0513 (19)0.0440 (17)0.0004 (15)0.0069 (15)0.0005 (15)
C90.094 (3)0.061 (2)0.062 (2)0.003 (2)0.006 (2)0.0136 (19)
C100.076 (2)0.075 (2)0.052 (2)0.003 (2)0.0224 (18)0.0053 (18)
C110.0509 (19)0.057 (2)0.0380 (16)0.0000 (15)0.0054 (14)0.0006 (15)
C120.0410 (18)0.0521 (19)0.0380 (16)0.0016 (14)0.0067 (13)0.0011 (14)
C130.0393 (17)0.0503 (19)0.0387 (16)0.0010 (14)0.0068 (13)0.0010 (14)
C140.0447 (18)0.0496 (19)0.0408 (16)0.0011 (15)0.0071 (14)0.0004 (14)
C150.0448 (18)0.061 (2)0.0414 (17)0.0014 (16)0.0035 (14)0.0038 (16)
C160.0428 (18)0.058 (2)0.0402 (17)0.0016 (15)0.0080 (14)0.0072 (15)
C170.055 (2)0.0459 (19)0.0473 (18)0.0052 (15)0.0164 (16)0.0009 (15)
C180.056 (2)0.089 (3)0.052 (2)0.0110 (19)0.0126 (17)0.0085 (19)
C190.067 (2)0.088 (3)0.073 (3)0.015 (2)0.031 (2)0.004 (2)
C200.086 (3)0.076 (3)0.057 (2)0.014 (2)0.034 (2)0.002 (2)
C210.076 (3)0.083 (3)0.048 (2)0.012 (2)0.0162 (19)0.0013 (19)
C220.057 (2)0.071 (2)0.0456 (19)0.0082 (17)0.0118 (16)0.0005 (17)
C230.0428 (19)0.075 (2)0.0446 (18)0.0009 (17)0.0035 (15)0.0145 (18)
C240.060 (2)0.112 (3)0.060 (2)0.021 (2)0.0109 (19)0.002 (2)
C250.063 (3)0.144 (4)0.085 (3)0.034 (3)0.009 (2)0.007 (3)
C260.047 (2)0.144 (4)0.100 (3)0.005 (3)0.018 (3)0.034 (3)
C270.057 (3)0.121 (4)0.084 (3)0.011 (3)0.025 (2)0.015 (3)
C280.048 (2)0.088 (3)0.068 (2)0.0096 (19)0.0129 (18)0.004 (2)
C290.048 (2)0.055 (2)0.0472 (18)0.0025 (16)0.0078 (15)0.0023 (16)
C300.050 (2)0.052 (2)0.0503 (19)0.0031 (16)0.0086 (16)0.0018 (16)
C310.065 (2)0.058 (2)0.060 (2)0.0074 (18)0.0022 (18)0.0090 (19)
C320.0477 (19)0.049 (2)0.061 (2)0.0011 (16)0.0181 (16)0.0033 (17)
C330.058 (2)0.058 (2)0.090 (3)0.0006 (19)0.021 (2)0.000 (2)
C340.081 (3)0.054 (3)0.128 (4)0.005 (2)0.039 (3)0.001 (3)
C350.098 (4)0.052 (3)0.124 (4)0.018 (3)0.041 (3)0.017 (3)
C360.085 (3)0.065 (3)0.086 (3)0.022 (2)0.025 (2)0.016 (2)
C370.061 (2)0.059 (2)0.064 (2)0.0093 (19)0.0185 (18)0.0118 (19)
C380.046 (2)0.0482 (19)0.0394 (17)0.0018 (16)0.0014 (14)0.0014 (14)
N10.0606 (17)0.0504 (17)0.0463 (15)0.0052 (13)0.0064 (13)0.0052 (14)
N20.0504 (18)0.072 (2)0.0608 (17)0.0055 (15)0.0096 (14)0.0013 (15)
N30.0464 (16)0.0569 (16)0.0442 (15)0.0036 (13)0.0098 (12)0.0047 (13)
N40.0437 (16)0.0666 (18)0.0463 (15)0.0016 (13)0.0067 (12)0.0095 (13)
N50.065 (2)0.070 (2)0.0615 (19)0.0029 (18)0.0039 (16)0.0120 (17)
N60.062 (2)0.089 (2)0.067 (2)0.0041 (17)0.0126 (16)0.0324 (18)
O10.0481 (15)0.0919 (18)0.0664 (15)0.0064 (13)0.0135 (12)0.0044 (13)
O20.0530 (15)0.0819 (18)0.0825 (17)0.0177 (13)0.0065 (13)0.0255 (14)
S10.1178 (10)0.0885 (8)0.0832 (7)0.0166 (7)0.0373 (7)0.0253 (6)
C390.093 (4)0.115 (6)0.115 (5)0.011 (5)0.031 (4)0.059 (4)
C400.152 (7)0.253 (9)0.067 (4)0.062 (7)0.054 (4)0.047 (6)
C410.163 (10)0.305 (14)0.252 (13)0.092 (9)0.115 (9)0.137 (11)
C39'0.120 (12)0.159 (14)0.086 (11)0.000 (12)0.012 (11)0.050 (12)
C40'0.106 (13)0.118 (13)0.121 (12)0.002 (12)0.038 (12)0.032 (11)
C41'0.18 (2)0.067 (15)0.111 (18)0.011 (16)0.033 (18)0.005 (13)
Geometric parameters (Å, º) top
C1—C21.358 (5)C21—H220.9300
C1—C61.378 (5)C22—H230.9300
C1—C81.505 (4)C23—C241.379 (5)
C2—C31.390 (5)C23—C281.384 (5)
C2—H20.9300C24—C251.375 (5)
C3—C41.354 (6)C24—H250.9300
C3—H30.9300C25—C261.373 (6)
C4—C51.362 (6)C25—H260.9300
C4—H40.9300C26—C271.366 (6)
C5—C61.380 (5)C26—H270.9300
C5—H50.9300C27—C281.378 (5)
C6—N61.392 (4)C27—H280.9300
C7—O11.222 (4)C28—H290.9300
C7—N61.351 (4)C29—O21.207 (3)
C7—C81.533 (4)C29—C301.440 (4)
C8—N11.468 (4)C30—C311.376 (4)
C8—C131.561 (4)C30—C321.437 (4)
C9—N11.435 (4)C31—N51.333 (4)
C9—S11.823 (4)C31—H320.9300
C9—H10A0.9700C32—C331.385 (4)
C9—H10B0.9700C32—C371.405 (4)
C10—C111.512 (4)C33—C341.381 (5)
C10—S11.798 (4)C33—H380.9300
C10—H11A0.9700C34—C351.381 (6)
C10—H11B0.9700C34—H370.9300
C11—N11.449 (4)C35—C361.349 (5)
C11—C121.552 (4)C35—H360.9300
C11—H120.9800C36—C371.388 (5)
C12—C381.462 (4)C36—H350.9300
C12—C131.550 (4)C37—N51.372 (5)
C12—C291.560 (4)C38—N21.137 (4)
C13—C141.505 (4)N3—N41.352 (3)
C13—H140.9800N5—H5A0.92 (4)
C14—C151.361 (4)N6—C391.454 (6)
C14—C161.416 (4)N6—C39'1.460 (11)
C15—N31.352 (4)C39—C401.465 (8)
C15—H160.9300C39—H39A0.9700
C16—N41.330 (4)C39—H39B0.9700
C16—C231.465 (4)C40—C411.147 (8)
C17—C221.372 (4)C40—H400.9300
C17—C181.373 (4)C41—H41A0.9300
C17—N31.416 (4)C41—H41B0.9300
C18—C191.374 (4)C39'—C40'1.466 (11)
C18—H190.9300C39'—H39C0.9700
C19—C201.365 (5)C39'—H39D0.9700
C19—H200.9300C40'—C41'1.307 (10)
C20—C211.357 (5)C40'—H40'0.9300
C20—H210.9300C41'—H41C0.9300
C21—C221.371 (4)C41'—H41D0.9300
C2—C1—C6118.9 (3)C28—C23—C16121.8 (3)
C2—C1—C8132.2 (3)C25—C24—C23120.6 (4)
C6—C1—C8108.7 (3)C25—C24—H25119.7
C1—C2—C3119.3 (4)C23—C24—H25119.7
C1—C2—H2120.4C26—C25—C24120.3 (4)
C3—C2—H2120.4C26—C25—H26119.9
C4—C3—C2120.5 (4)C24—C25—H26119.9
C4—C3—H3119.7C27—C26—C25119.8 (4)
C2—C3—H3119.7C27—C26—H27120.1
C3—C4—C5121.7 (4)C25—C26—H27120.1
C3—C4—H4119.1C26—C27—C28120.2 (4)
C5—C4—H4119.1C26—C27—H28119.9
C4—C5—C6117.1 (4)C28—C27—H28119.9
C4—C5—H5121.5C27—C28—C23120.7 (4)
C6—C5—H5121.5C27—C28—H29119.7
C1—C6—C5122.5 (4)C23—C28—H29119.7
C1—C6—N6109.9 (3)O2—C29—C30123.2 (3)
C5—C6—N6127.6 (4)O2—C29—C12118.5 (3)
O1—C7—N6125.5 (3)C30—C29—C12118.2 (3)
O1—C7—C8126.2 (3)C31—C30—C32105.7 (3)
N6—C7—C8108.3 (3)C31—C30—C29126.8 (3)
N1—C8—C1121.2 (3)C32—C30—C29127.4 (3)
N1—C8—C7107.4 (2)N5—C31—C30110.7 (3)
C1—C8—C7101.5 (3)N5—C31—H32124.6
N1—C8—C13103.7 (2)C30—C31—H32124.6
C1—C8—C13109.9 (2)C33—C32—C37118.2 (3)
C7—C8—C13113.5 (2)C33—C32—C30135.2 (3)
N1—C9—S1108.5 (2)C37—C32—C30106.4 (3)
N1—C9—H10A110.0C34—C33—C32118.5 (4)
S1—C9—H10A110.0C34—C33—H38120.8
N1—C9—H10B110.0C32—C33—H38120.8
S1—C9—H10B110.0C35—C34—C33121.6 (4)
H10A—C9—H10B108.4C35—C34—H37119.2
C11—C10—S1104.4 (2)C33—C34—H37119.2
C11—C10—H11A110.9C36—C35—C34121.7 (4)
S1—C10—H11A110.9C36—C35—H36119.2
C11—C10—H11B110.9C34—C35—H36119.2
S1—C10—H11B110.9C35—C36—C37117.1 (4)
H11A—C10—H11B108.9C35—C36—H35121.4
N1—C11—C10109.2 (3)C37—C36—H35121.4
N1—C11—C12103.3 (2)N5—C37—C36129.5 (4)
C10—C11—C12116.2 (3)N5—C37—C32107.7 (3)
N1—C11—H12109.3C36—C37—C32122.9 (4)
C10—C11—H12109.3N2—C38—C12177.0 (3)
C12—C11—H12109.3C9—N1—C11109.6 (2)
C38—C12—C13112.6 (2)C9—N1—C8120.2 (3)
C38—C12—C11109.6 (2)C11—N1—C8111.9 (2)
C13—C12—C11101.4 (2)N4—N3—C15111.3 (2)
C38—C12—C29107.9 (2)N4—N3—C17120.9 (2)
C13—C12—C29112.0 (2)C15—N3—C17127.7 (3)
C11—C12—C29113.5 (2)C16—N4—N3105.5 (2)
C14—C13—C12118.9 (2)C31—N5—C37109.4 (3)
C14—C13—C8113.9 (2)C31—N5—H5A122 (3)
C12—C13—C8105.6 (2)C37—N5—H5A129 (3)
C14—C13—H14105.8C7—N6—C6111.3 (3)
C12—C13—H14105.8C7—N6—C39124.7 (6)
C8—C13—H14105.8C6—N6—C39124.0 (6)
C15—C14—C16104.7 (3)C7—N6—C39'116 (3)
C15—C14—C13128.9 (3)C6—N6—C39'131 (2)
C16—C14—C13125.8 (3)C39—N6—C39'17 (2)
N3—C15—C14107.8 (3)C10—S1—C992.97 (16)
N3—C15—H16126.1N6—C39—C40107.7 (5)
C14—C15—H16126.1N6—C39—H39A110.2
N4—C16—C14110.7 (3)C40—C39—H39A110.2
N4—C16—C23119.9 (3)N6—C39—H39B110.2
C14—C16—C23129.4 (3)C40—C39—H39B110.2
C22—C17—C18119.7 (3)H39A—C39—H39B108.5
C22—C17—N3119.7 (3)C41—C40—C39143.9 (12)
C18—C17—N3120.6 (3)C41—C40—H40108.0
C17—C18—C19120.0 (3)C39—C40—H40108.0
C17—C18—H19120.0C40—C41—H41A120.0
C19—C18—H19120.0C40—C41—H41B120.0
C20—C19—C18120.2 (4)H41A—C41—H41B120.0
C20—C19—H20119.9N6—C39'—C40'107.0 (19)
C18—C19—H20119.9N6—C39'—H39C110.3
C21—C20—C19119.5 (3)C40'—C39'—H39C110.3
C21—C20—H21120.2N6—C39'—H39D110.3
C19—C20—H21120.2C40'—C39'—H39D110.3
C20—C21—C22121.2 (3)H39C—C39'—H39D108.6
C20—C21—H22119.4C41'—C40'—C39'136 (4)
C22—C21—H22119.4C41'—C40'—H40'112.1
C21—C22—C17119.4 (3)C39'—C40'—H40'112.1
C21—C22—H23120.3C40'—C41'—H41C120.0
C17—C22—H23120.3C40'—C41'—H41D120.0
C24—C23—C28118.5 (3)H41C—C41'—H41D120.0
C24—C23—C16119.7 (3)
C6—C1—C2—C30.2 (5)C11—C12—C29—O2113.1 (3)
C8—C1—C2—C3173.9 (3)C38—C12—C29—C3051.9 (3)
C1—C2—C3—C40.2 (6)C13—C12—C29—C30176.3 (3)
C2—C3—C4—C50.4 (7)C11—C12—C29—C3069.7 (3)
C3—C4—C5—C60.2 (7)O2—C29—C30—C31165.7 (3)
C2—C1—C6—C50.4 (5)C12—C29—C30—C3117.3 (5)
C8—C1—C6—C5175.0 (3)O2—C29—C30—C3217.4 (5)
C2—C1—C6—N6179.8 (3)C12—C29—C30—C32159.6 (3)
C8—C1—C6—N64.8 (4)C32—C30—C31—N50.2 (4)
C4—C5—C6—C10.2 (6)C29—C30—C31—N5177.2 (3)
C4—C5—C6—N6180.0 (4)C31—C30—C32—C33176.8 (4)
C2—C1—C8—N161.0 (5)C29—C30—C32—C330.7 (6)
C6—C1—C8—N1124.4 (3)C31—C30—C32—C371.6 (4)
C2—C1—C8—C7179.6 (4)C29—C30—C32—C37175.9 (3)
C6—C1—C8—C75.8 (3)C37—C32—C33—C340.1 (5)
C2—C1—C8—C1360.0 (4)C30—C32—C33—C34174.8 (4)
C6—C1—C8—C13114.6 (3)C32—C33—C34—C350.0 (6)
O1—C7—C8—N145.5 (4)C33—C34—C35—C360.5 (7)
N6—C7—C8—N1133.1 (3)C34—C35—C36—C370.9 (6)
O1—C7—C8—C1173.6 (3)C35—C36—C37—N5177.8 (4)
N6—C7—C8—C15.0 (3)C35—C36—C37—C321.0 (6)
O1—C7—C8—C1368.6 (4)C33—C32—C37—N5178.5 (3)
N6—C7—C8—C13112.8 (3)C30—C32—C37—N52.3 (4)
S1—C10—C11—N137.1 (3)C33—C32—C37—C360.6 (5)
S1—C10—C11—C12153.4 (2)C30—C32—C37—C36176.7 (3)
N1—C11—C12—C3882.0 (3)C13—C12—C38—N2130 (6)
C10—C11—C12—C38158.4 (3)C11—C12—C38—N2118 (6)
N1—C11—C12—C1337.1 (3)C29—C12—C38—N26 (6)
C10—C11—C12—C1382.4 (3)S1—C9—N1—C1126.7 (3)
N1—C11—C12—C29157.3 (2)S1—C9—N1—C8105.0 (3)
C10—C11—C12—C2937.8 (4)C10—C11—N1—C942.3 (3)
C38—C12—C13—C1443.6 (4)C12—C11—N1—C9166.6 (3)
C11—C12—C13—C14160.6 (2)C10—C11—N1—C893.6 (3)
C29—C12—C13—C1478.1 (3)C12—C11—N1—C830.7 (3)
C38—C12—C13—C885.7 (3)C1—C8—N1—C917.2 (4)
C11—C12—C13—C831.3 (3)C7—C8—N1—C998.4 (3)
C29—C12—C13—C8152.6 (2)C13—C8—N1—C9141.1 (3)
N1—C8—C13—C14146.4 (2)C1—C8—N1—C11113.4 (3)
C1—C8—C13—C1482.7 (3)C7—C8—N1—C11131.0 (3)
C7—C8—C13—C1430.1 (3)C13—C8—N1—C1110.5 (3)
N1—C8—C13—C1214.1 (3)C14—C15—N3—N41.2 (3)
C1—C8—C13—C12145.1 (2)C14—C15—N3—C17176.7 (3)
C7—C8—C13—C12102.1 (3)C22—C17—N3—N43.0 (4)
C12—C13—C14—C1551.9 (4)C18—C17—N3—N4178.5 (3)
C8—C13—C14—C1573.5 (4)C22—C17—N3—C15172.0 (3)
C12—C13—C14—C16139.0 (3)C18—C17—N3—C156.4 (5)
C8—C13—C14—C1695.6 (3)C14—C16—N4—N30.1 (3)
C16—C14—C15—N31.1 (3)C23—C16—N4—N3177.1 (3)
C13—C14—C15—N3172.0 (3)C15—N3—N4—C160.8 (3)
C15—C14—C16—N40.7 (4)C17—N3—N4—C16176.6 (3)
C13—C14—C16—N4171.9 (3)C30—C31—N5—C371.2 (4)
C15—C14—C16—C23176.0 (3)C36—C37—N5—C31176.7 (4)
C13—C14—C16—C234.7 (5)C32—C37—N5—C312.2 (4)
C22—C17—C18—C191.3 (5)O1—C7—N6—C6176.1 (3)
N3—C17—C18—C19177.2 (3)C8—C7—N6—C62.5 (4)
C17—C18—C19—C200.4 (6)O1—C7—N6—C390.8 (6)
C18—C19—C20—C210.5 (6)C8—C7—N6—C39179.4 (4)
C19—C20—C21—C220.4 (6)O1—C7—N6—C39'17.8 (15)
C20—C21—C22—C170.6 (5)C8—C7—N6—C39'163.6 (14)
C18—C17—C22—C211.4 (5)C1—C6—N6—C71.4 (4)
N3—C17—C22—C21177.1 (3)C5—C6—N6—C7178.3 (4)
N4—C16—C23—C2451.8 (4)C1—C6—N6—C39175.5 (5)
C14—C16—C23—C24124.6 (4)C5—C6—N6—C394.7 (7)
N4—C16—C23—C28129.7 (3)C1—C6—N6—C39'165 (2)
C14—C16—C23—C2854.0 (5)C5—C6—N6—C39'15 (2)
C28—C23—C24—C250.2 (6)C11—C10—S1—C918.3 (3)
C16—C23—C24—C25178.4 (4)N1—C9—S1—C104.0 (3)
C23—C24—C25—C260.0 (7)C7—N6—C39—C4097.6 (8)
C24—C25—C26—C270.1 (7)C6—N6—C39—C4085.8 (9)
C25—C26—C27—C280.5 (7)C39'—N6—C39—C4035 (8)
C26—C27—C28—C230.8 (6)N6—C39—C40—C4185 (2)
C24—C23—C28—C270.7 (5)C7—N6—C39'—C40'84 (4)
C16—C23—C28—C27177.9 (3)C6—N6—C39'—C40'113 (3)
C38—C12—C29—O2125.3 (3)C39—N6—C39'—C40'41 (5)
C13—C12—C29—O20.9 (4)N6—C39'—C40'—C41'108 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5A···O1i0.92 (4)1.92 (4)2.822 (4)166 (3)
Symmetry code: (i) x, y, z+1.

Experimental details

Crystal data
Chemical formulaC41H32N6O2S
Mr672.80
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)10.7396 (10), 16.3471 (14), 20.112 (2)
β (°) 105.485 (4)
V3)3402.7 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.14
Crystal size (mm)0.30 × 0.25 × 0.20
Data collection
DiffractometerBruker SMART APEXII area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2008)
Tmin, Tmax0.958, 0.972
No. of measured, independent and
observed [I > 2σ(I)] reflections
25634, 5983, 3281
Rint0.049
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.146, 1.06
No. of reflections5983
No. of parameters483
No. of restraints48
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.40, 0.30

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5A···O1i0.92 (4)1.92 (4)2.822 (4)166 (3)
Symmetry code: (i) x, y, z+1.
 

Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and BioPhysics, University of Madras, Chennai, India, for the data collection.

References

First citationBruker. (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationCremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  CrossRef CAS Web of Science
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals
First citationFerguson, N. M., Cummings, D. A. T., Cauchemez, S., Fraser, C., Riley, S., Meeyai, A., Iamsirithaworn, S. & Burke, D. S. (2005). Nature (London), 437, 209–214.  Web of Science CrossRef PubMed CAS
First citationJagadeesan, G., Sethusankar, K., Prasanna, R. & Raghunathan, R. (2012a). Acta Cryst. E68, o382–o383.  Web of Science CSD CrossRef CAS IUCr Journals
First citationJagadeesan, G., Sethusankar, K., Prasanna, R. & Raghunathan, R. (2012b). Acta Cryst. E68, o2505–o2506.  CSD CrossRef CAS IUCr Journals
First citationKilonda, A., Compernolle, F. & Hoornaert, G. J. (1995). J. Org. Chem. 60, 5820–5824.  CrossRef CAS Web of Science
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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Volume 69| Part 6| June 2013| Pages o857-o858
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