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ISSN: 2056-9890

Crystal structure of 3′-(1H-indole-3-carbon­yl)-1′-methyl-2-oxo-4′-(4-oxo-4H-chromen-3-yl)spiro­[indoline-3,2′-pyrrolidine]-3′-carbo­nitrile

aDepartment of Physics, Queen Mary's College (Autonomous), Chennai 600 004, India, bDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, and cIndustrial Chemistry Laboratory, Central Leather Research Institute, Adyar, Chennai 600 020, India
*Correspondence e-mail: aspandian59@gmail.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 15 September 2015; accepted 26 October 2015; online 31 October 2015)

In the title compound, C31H22N4O4, the pyrrolidine ring adopts a twist conformation on the N—CH2 bond. The indolin-2-one and the 1H-indole rings are nearly planar (r.m.s. deviations = 0.06 and 0.011 Å, respectively) and are inclined to one another by 34.19 (9)°. The chromene ring system is also nearly planar (r.m.s. deviation = 0.029 Å). It is almost normal to the 1H-indole ring system, with a dihedral angle of 88.71 (8)°, and is inclined to the indolin-2-one ring system by 72.76 (8)°. In the crystal, mol­ecules are linked via N—H⋯O hydrogen bonds, forming slabs parallel to (10-1). The slabs are linked by C—H⋯O hydrogen bonds, forming a three-dimensional structure.

1. Related literature

For the biological activities of indole derivatives, see: Macor et al. (1992[Macor, J. E., Fox, C. B., Johnson, C., Koe, B. K., Lebel, L. A. & Zorn, S. H. (1992). J. Med. Chem. 35, 3625-3632.]); Andreani et al. (2001[Andreani, A., Granaiola, M., Leoni, A., Locatelli, A., Morigi, R., Rambaldi, M., Giorgi, G., Salvini, L. & Garaliene, V. (2001). Anticancer Drug. Des. 16, 167-174.]); Quetin-Leclercq (1994[Quetin-Leclercq, J. (1994). J. Pharm. Belg. 49, 181-192.]); Mukhopadhyay et al. (1981[Mukhopadhyay, S., Handy, G. A., Funayama, S. & Cordell, G. A. (1981). J. Nat. Prod. 44, 696-700.]); Singh et al. (2000[Singh, U. P., Sarma, B. K., Mishra, P. K. & Ray, A. B. (2000). Fol. Microbiol. 45, 173-176.]). For the structure of a very similar compound, see: Ramesh et al. (2009[Ramesh, P., Sundaresan, S. S., Lakshmi, N. V., Perumal, P. T. & Ponnuswamy, M. N. (2009). Acta Cryst. E65, o1945.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C31H22N4O4

  • Mr = 514.53

  • Monoclinic, P 21 /n

  • a = 13.0401 (5) Å

  • b = 14.9139 (6) Å

  • c = 13.7161 (5) Å

  • β = 112.603 (2)°

  • V = 2462.60 (16) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 293 K

  • 0.35 × 0.30 × 0.30 mm

2.2. Data collection

  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.969, Tmax = 0.974

  • 16591 measured reflections

  • 4341 independent reflections

  • 3234 reflections with I > 2σ(I)

  • Rint = 0.030

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.049

  • wR(F2) = 0.132

  • S = 1.04

  • 4329 reflections

  • 353 parameters

  • H-atom parameters constrained

  • Δρmax = 0.29 e Å−3

  • Δρmin = −0.18 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N3—H3A⋯O4i 0.86 2.14 2.967 (3) 161
N4—H4A⋯O3ii 0.86 2.06 2.866 (3) 156
C29—H29⋯O2iii 0.93 2.59 3.267 (3) 131
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) x, y, z+1.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97 and PLATON.

Supporting information


Structural commentary top

The chemistry of indole has been of increasing inter­est, since several compounds of this type possess diverse biological activities (Macor et al., 1992). These derivatives exhibit anti­bacterial, anti­fungal (Singh et al., 2000) and anti­tumour activities (Andreani et al., 2001). Some of the indole alkaloids extracted from plants possess inter­esting cytotoxic and anti­parasitic properties (Quetin-Leclercq, 1994; Mukhopadhyay et al., 1981).

The geometric parameters of the title molecule (Fig. 1) agree well with those reported for a similar compound, 1'-methyl-2,2''-dioxoindoline-3-spiro-2'-pyrrolidine-3'-spiro-3''-indoline-4',4'-dicarbo­nitrile (Ramesh et al., 2009). The pyrrolidine ring (N2/C10/C11/C13/C21) adopts a twist conformation on bond N2—C21: puckering parameters and the asymmetry parameters for this ring are q2 = 0.411 (2) Å, φ2 = 160.3 (3)° nd ΔCs(C11) = 1.3 (2)°. Both indole rings, (N3/24–31) and (N4/C13—C20), are planar [maximum deviations of 0.013 Å for C27 and 0.080 (1) Å for C13 in the two rings] and are oriented at a dihedral angle of 34.19 (9)°. The sum of the bond angles around atom N2 of the central pyrrolidine ring is 337° as expected for sp3 hybridization.

In the crystal, molecules are linked by N—H···O hydrogen bonds forming slabs parallel to (101). The slabs are linked via C—H···O hydrogen bonds forming a three-dimensional structure (Table 1 and Fig. 2).

Synthesis and crystallization top

A mixture of isatin2a-f (1.0 mmol), sarcosine3 (1.1 mmol) and (E)-2-(1H-indole -3-carbonyl)-3-(4-oxo-4H-chromen-3-yl)acrylo­nitrile 1 (1.2 mmol) in methanol was stirred at room temperature for 120 min. The solid precipitated during the reaction mixture was filtered and dried under vacuum to obtain spiro­oxindoles5a-f in crude form. The resulting crude product was purified by flash column chromatography (mesh 100–200) using hexane/EtOAC (7:3). The solid single product was finally recrystallized from ethanol, giving title compound in good yield as colourless block-like crystals.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. N and C-bound H atoms were positioned geometrically (N—H = 0.86 Å, C–H = 0.93–0.98 Å) and allowed to ride on their parent atoms, with Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(N,C) for other H atoms.

Related literature top

For the biological activities of indole derivatives, see: Macor et al. (1992); Andreani et al. (2001); Quetin-Leclercq (1994); Mukhopadhyay et al. (1981); Singh et al. (2000). For the structure of a very similar compound, see: Ramesh et al. (2009).

Structure description top

The chemistry of indole has been of increasing inter­est, since several compounds of this type possess diverse biological activities (Macor et al., 1992). These derivatives exhibit anti­bacterial, anti­fungal (Singh et al., 2000) and anti­tumour activities (Andreani et al., 2001). Some of the indole alkaloids extracted from plants possess inter­esting cytotoxic and anti­parasitic properties (Quetin-Leclercq, 1994; Mukhopadhyay et al., 1981).

The geometric parameters of the title molecule (Fig. 1) agree well with those reported for a similar compound, 1'-methyl-2,2''-dioxoindoline-3-spiro-2'-pyrrolidine-3'-spiro-3''-indoline-4',4'-dicarbo­nitrile (Ramesh et al., 2009). The pyrrolidine ring (N2/C10/C11/C13/C21) adopts a twist conformation on bond N2—C21: puckering parameters and the asymmetry parameters for this ring are q2 = 0.411 (2) Å, φ2 = 160.3 (3)° nd ΔCs(C11) = 1.3 (2)°. Both indole rings, (N3/24–31) and (N4/C13—C20), are planar [maximum deviations of 0.013 Å for C27 and 0.080 (1) Å for C13 in the two rings] and are oriented at a dihedral angle of 34.19 (9)°. The sum of the bond angles around atom N2 of the central pyrrolidine ring is 337° as expected for sp3 hybridization.

In the crystal, molecules are linked by N—H···O hydrogen bonds forming slabs parallel to (101). The slabs are linked via C—H···O hydrogen bonds forming a three-dimensional structure (Table 1 and Fig. 2).

For the biological activities of indole derivatives, see: Macor et al. (1992); Andreani et al. (2001); Quetin-Leclercq (1994); Mukhopadhyay et al. (1981); Singh et al. (2000). For the structure of a very similar compound, see: Ramesh et al. (2009).

Synthesis and crystallization top

A mixture of isatin2a-f (1.0 mmol), sarcosine3 (1.1 mmol) and (E)-2-(1H-indole -3-carbonyl)-3-(4-oxo-4H-chromen-3-yl)acrylo­nitrile 1 (1.2 mmol) in methanol was stirred at room temperature for 120 min. The solid precipitated during the reaction mixture was filtered and dried under vacuum to obtain spiro­oxindoles5a-f in crude form. The resulting crude product was purified by flash column chromatography (mesh 100–200) using hexane/EtOAC (7:3). The solid single product was finally recrystallized from ethanol, giving title compound in good yield as colourless block-like crystals.

Refinement details top

Crystal data, data collection and structure refinement details are summarized in Table 2. N and C-bound H atoms were positioned geometrically (N—H = 0.86 Å, C–H = 0.93–0.98 Å) and allowed to ride on their parent atoms, with Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(N,C) for other H atoms.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); 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 atom labelling. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. A view along the b axis of the crystal packing of the title compound. The hydrogen bonds are shown as dashed lines (see Table 1).
3'-(1H-Indole-3-carbonyl)-1'-methyl-2-oxo-4'-(4-oxo-4H-chromen-3-yl)spiro[indoline-3,2'-pyrrolidine]-3'-carbonitrile top
Crystal data top
C31H22N4O4F(000) = 1072
Mr = 514.53Dx = 1.388 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybnCell parameters from 4241 reflections
a = 13.0401 (5) Åθ = 1.8–25.0°
b = 14.9139 (6) ŵ = 0.09 mm1
c = 13.7161 (5) ÅT = 293 K
β = 112.603 (2)°Block, colourless
V = 2462.60 (16) Å30.35 × 0.30 × 0.30 mm
Z = 4
Data collection top
Bruker Kappa APEXII CCD
diffractometer
4341 independent reflections
Radiation source: fine-focus sealed tube3234 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
ω and φ scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
h = 1415
Tmin = 0.969, Tmax = 0.974k = 1717
16591 measured reflectionsl = 1616
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) = 0.132H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0575P)2 + 1.2814P]
where P = (Fo2 + 2Fc2)/3
4329 reflections(Δ/σ)max < 0.001
353 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.18 e Å3
Crystal data top
C31H22N4O4V = 2462.60 (16) Å3
Mr = 514.53Z = 4
Monoclinic, P21/nMo Kα radiation
a = 13.0401 (5) ŵ = 0.09 mm1
b = 14.9139 (6) ÅT = 293 K
c = 13.7161 (5) Å0.35 × 0.30 × 0.30 mm
β = 112.603 (2)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer
4341 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
3234 reflections with I > 2σ(I)
Tmin = 0.969, Tmax = 0.974Rint = 0.030
16591 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.132H-atom parameters constrained
S = 1.04Δρmax = 0.29 e Å3
4329 reflectionsΔρmin = 0.18 e Å3
353 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
C10.2880 (2)0.25426 (16)0.10673 (17)0.0378 (6)
H10.27370.31520.11930.045*
C20.36735 (18)0.12268 (16)0.14083 (15)0.0353 (5)
C30.4277 (2)0.08350 (19)0.19416 (18)0.0467 (6)
H30.45420.11780.23610.056*
C40.4468 (2)0.00645 (19)0.18327 (19)0.0517 (7)
H40.48670.03380.21860.062*
C50.4078 (2)0.05821 (18)0.1203 (2)0.0498 (7)
H50.42010.11980.11530.060*
C60.35133 (19)0.01845 (17)0.06596 (19)0.0427 (6)
H60.32690.05290.02260.051*
C70.33001 (17)0.07404 (15)0.07526 (15)0.0325 (5)
C80.27094 (18)0.11941 (15)0.01806 (15)0.0340 (5)
C90.24912 (18)0.21424 (15)0.04083 (15)0.0307 (5)
C100.18396 (18)0.26261 (15)0.01285 (15)0.0321 (5)
H100.12430.22270.01300.039*
C110.25597 (17)0.28881 (15)0.13121 (15)0.0298 (5)
C120.3687 (2)0.25089 (15)0.16436 (16)0.0338 (5)
C130.26070 (17)0.39617 (15)0.13015 (15)0.0315 (5)
C140.1881 (2)0.43664 (17)0.18886 (18)0.0424 (6)
C150.3657 (2)0.48427 (17)0.27711 (19)0.0464 (6)
C160.4568 (3)0.52655 (19)0.3503 (2)0.0641 (9)
H160.45300.55480.40930.077*
C170.5530 (3)0.5251 (2)0.3323 (3)0.0734 (10)
H170.61590.55290.38040.088*
C180.5596 (2)0.4835 (2)0.2449 (3)0.0683 (9)
H180.62560.48560.23380.082*
C190.4675 (2)0.43842 (19)0.1731 (2)0.0507 (7)
H190.47150.40950.11460.061*
C200.37124 (19)0.43801 (16)0.19138 (17)0.0378 (6)
C210.13173 (19)0.35150 (16)0.03531 (16)0.0382 (6)
H21A0.11290.35220.11100.046*
H21B0.06530.36350.02170.046*
C220.1867 (2)0.50981 (18)0.0085 (2)0.0581 (8)
H22A0.16940.51950.08230.087*
H22B0.24730.54790.03250.087*
H22C0.12270.52360.00730.087*
C230.19977 (18)0.25368 (15)0.20664 (16)0.0331 (5)
C240.25979 (18)0.25638 (15)0.32050 (16)0.0339 (5)
C250.21092 (18)0.23643 (15)0.39638 (16)0.0338 (5)
C260.1073 (2)0.20842 (18)0.39024 (19)0.0472 (6)
H260.05000.19870.32510.057*
C270.0911 (2)0.1953 (2)0.4831 (2)0.0603 (8)
H270.02220.17570.47990.072*
C280.1754 (2)0.2107 (2)0.5811 (2)0.0555 (7)
H280.16150.20200.64210.067*
C290.2784 (2)0.23842 (17)0.58952 (18)0.0456 (6)
H290.33500.24870.65490.055*
C300.29469 (19)0.25050 (16)0.49630 (16)0.0359 (5)
C310.36911 (19)0.27949 (17)0.37844 (17)0.0412 (6)
H310.42080.29500.34990.049*
N10.45588 (18)0.22200 (15)0.18987 (16)0.0502 (6)
N20.21796 (16)0.41585 (13)0.01775 (13)0.0390 (5)
N30.38947 (16)0.27611 (14)0.48210 (14)0.0430 (5)
H3A0.45220.28810.53200.052*
N40.25757 (18)0.48177 (15)0.27375 (16)0.0521 (6)
H4A0.23750.50620.32040.063*
O10.08831 (15)0.42855 (14)0.16214 (15)0.0609 (5)
O20.34652 (14)0.21307 (11)0.15668 (12)0.0435 (4)
O30.24130 (15)0.08041 (11)0.04650 (13)0.0511 (5)
O40.10336 (13)0.22832 (12)0.16760 (12)0.0457 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0488 (14)0.0357 (13)0.0302 (11)0.0036 (11)0.0165 (11)0.0004 (10)
C20.0390 (13)0.0396 (14)0.0232 (10)0.0015 (11)0.0072 (9)0.0036 (9)
C30.0508 (15)0.0603 (18)0.0311 (12)0.0063 (13)0.0180 (11)0.0023 (11)
C40.0495 (16)0.0614 (19)0.0413 (14)0.0121 (14)0.0144 (12)0.0139 (13)
C50.0469 (15)0.0412 (15)0.0549 (15)0.0063 (12)0.0124 (13)0.0107 (12)
C60.0378 (14)0.0402 (15)0.0454 (14)0.0025 (11)0.0108 (11)0.0007 (11)
C70.0338 (12)0.0348 (13)0.0242 (10)0.0015 (10)0.0060 (9)0.0028 (9)
C80.0406 (13)0.0360 (13)0.0226 (10)0.0039 (10)0.0091 (9)0.0006 (9)
C90.0364 (12)0.0328 (12)0.0193 (10)0.0038 (10)0.0069 (9)0.0030 (9)
C100.0319 (12)0.0381 (13)0.0229 (10)0.0020 (10)0.0068 (9)0.0032 (9)
C110.0288 (11)0.0360 (13)0.0213 (10)0.0038 (10)0.0061 (9)0.0026 (9)
C120.0371 (13)0.0382 (14)0.0242 (10)0.0036 (11)0.0098 (10)0.0052 (9)
C130.0305 (11)0.0347 (13)0.0260 (10)0.0049 (10)0.0074 (9)0.0026 (9)
C140.0425 (15)0.0451 (15)0.0397 (13)0.0098 (12)0.0160 (11)0.0009 (11)
C150.0494 (16)0.0387 (14)0.0400 (13)0.0073 (12)0.0046 (11)0.0077 (11)
C160.063 (2)0.0510 (18)0.0545 (17)0.0071 (15)0.0035 (15)0.0207 (13)
C170.0541 (19)0.0541 (19)0.083 (2)0.0019 (15)0.0054 (16)0.0189 (17)
C180.0353 (15)0.063 (2)0.095 (2)0.0018 (14)0.0114 (15)0.0006 (18)
C190.0374 (14)0.0514 (17)0.0585 (16)0.0003 (12)0.0133 (12)0.0029 (13)
C200.0346 (13)0.0354 (13)0.0372 (12)0.0033 (11)0.0070 (10)0.0001 (10)
C210.0389 (13)0.0449 (15)0.0240 (11)0.0047 (11)0.0045 (10)0.0018 (10)
C220.0685 (19)0.0431 (16)0.0476 (15)0.0043 (14)0.0055 (13)0.0095 (12)
C230.0322 (13)0.0363 (13)0.0273 (11)0.0027 (10)0.0076 (10)0.0001 (9)
C240.0347 (13)0.0396 (14)0.0260 (11)0.0013 (10)0.0100 (10)0.0009 (9)
C250.0369 (13)0.0367 (13)0.0262 (11)0.0080 (10)0.0104 (9)0.0054 (9)
C260.0372 (14)0.0653 (18)0.0364 (13)0.0044 (13)0.0112 (11)0.0117 (12)
C270.0465 (16)0.087 (2)0.0538 (17)0.0042 (15)0.0263 (14)0.0180 (15)
C280.0637 (18)0.074 (2)0.0369 (14)0.0116 (15)0.0283 (13)0.0134 (13)
C290.0552 (16)0.0538 (16)0.0269 (11)0.0094 (13)0.0148 (11)0.0038 (11)
C300.0390 (13)0.0385 (14)0.0283 (11)0.0065 (11)0.0109 (10)0.0022 (9)
C310.0377 (13)0.0580 (16)0.0263 (11)0.0042 (12)0.0105 (10)0.0017 (10)
N10.0426 (13)0.0590 (15)0.0451 (12)0.0159 (11)0.0126 (10)0.0065 (10)
N20.0431 (11)0.0376 (11)0.0290 (9)0.0023 (9)0.0058 (8)0.0027 (8)
N30.0371 (11)0.0631 (14)0.0225 (9)0.0068 (10)0.0044 (8)0.0026 (9)
N40.0581 (14)0.0577 (14)0.0411 (12)0.0102 (11)0.0196 (11)0.0165 (10)
O10.0446 (12)0.0786 (14)0.0649 (12)0.0107 (10)0.0269 (9)0.0055 (10)
O20.0595 (11)0.0454 (11)0.0336 (8)0.0034 (8)0.0269 (8)0.0051 (7)
O30.0732 (12)0.0463 (11)0.0445 (9)0.0007 (9)0.0344 (9)0.0102 (8)
O40.0334 (9)0.0706 (12)0.0293 (8)0.0076 (9)0.0080 (7)0.0009 (8)
Geometric parameters (Å, º) top
C1—C91.335 (3)C16—H160.9300
C1—O21.353 (3)C17—C181.381 (5)
C1—H10.9300C17—H170.9300
C2—O21.376 (3)C18—C191.398 (4)
C2—C71.382 (3)C18—H180.9300
C2—C31.392 (3)C19—C201.372 (3)
C3—C41.362 (4)C19—H190.9300
C3—H30.9300C21—N21.444 (3)
C4—C51.392 (4)C21—H21A0.9700
C4—H40.9300C21—H21B0.9700
C5—C61.369 (3)C22—N21.465 (3)
C5—H50.9300C22—H22A0.9600
C6—C71.403 (3)C22—H22B0.9600
C6—H60.9300C22—H22C0.9600
C7—C81.460 (3)C23—O41.222 (3)
C8—O31.239 (3)C23—C241.454 (3)
C8—C91.453 (3)C24—C311.383 (3)
C9—C101.505 (3)C24—C251.445 (3)
C10—C211.521 (3)C25—C261.385 (3)
C10—C111.581 (3)C25—C301.402 (3)
C10—H100.9800C26—C271.383 (3)
C11—C121.474 (3)C26—H260.9300
C11—C231.570 (3)C27—C281.390 (4)
C11—C131.603 (3)C27—H270.9300
C12—N11.138 (3)C28—C291.367 (4)
C13—N21.454 (3)C28—H280.9300
C13—C201.497 (3)C29—C301.386 (3)
C13—C141.580 (3)C29—H290.9300
C14—O11.214 (3)C30—N31.377 (3)
C14—N41.349 (3)C31—N31.343 (3)
C15—C161.378 (4)C31—H310.9300
C15—C201.389 (3)N3—H3A0.8600
C15—N41.393 (3)N4—H4A0.8600
C16—C171.369 (4)
C9—C1—O2125.1 (2)C17—C18—C19120.3 (3)
C9—C1—H1117.5C17—C18—H18119.9
O2—C1—H1117.5C19—C18—H18119.9
O2—C2—C7121.33 (19)C20—C19—C18118.2 (3)
O2—C2—C3116.4 (2)C20—C19—H19120.9
C7—C2—C3122.2 (2)C18—C19—H19120.9
C4—C3—C2118.2 (2)C19—C20—C15120.1 (2)
C4—C3—H3120.9C19—C20—C13130.6 (2)
C2—C3—H3120.9C15—C20—C13109.3 (2)
C3—C4—C5121.3 (2)N2—C21—C10103.20 (17)
C3—C4—H4119.4N2—C21—H21A111.1
C5—C4—H4119.4C10—C21—H21A111.1
C6—C5—C4119.9 (2)N2—C21—H21B111.1
C6—C5—H5120.0C10—C21—H21B111.1
C4—C5—H5120.0H21A—C21—H21B109.1
C5—C6—C7120.4 (2)N2—C22—H22A109.5
C5—C6—H6119.8N2—C22—H22B109.5
C7—C6—H6119.8H22A—C22—H22B109.5
C2—C7—C6117.9 (2)N2—C22—H22C109.5
C2—C7—C8119.8 (2)H22A—C22—H22C109.5
C6—C7—C8122.3 (2)H22B—C22—H22C109.5
O3—C8—C9121.4 (2)O4—C23—C24121.2 (2)
O3—C8—C7122.7 (2)O4—C23—C11118.47 (18)
C9—C8—C7115.85 (18)C24—C23—C11120.25 (19)
C1—C9—C8119.1 (2)C31—C24—C25106.26 (18)
C1—C9—C10123.3 (2)C31—C24—C23129.4 (2)
C8—C9—C10117.54 (18)C25—C24—C23124.3 (2)
C9—C10—C21116.64 (18)C26—C25—C30118.7 (2)
C9—C10—C11113.37 (17)C26—C25—C24135.1 (2)
C21—C10—C11102.75 (16)C30—C25—C24106.2 (2)
C9—C10—H10107.9C27—C26—C25118.5 (2)
C21—C10—H10107.9C27—C26—H26120.7
C11—C10—H10107.9C25—C26—H26120.7
C12—C11—C23109.35 (17)C26—C27—C28121.6 (3)
C12—C11—C10110.51 (16)C26—C27—H27119.2
C23—C11—C10110.54 (17)C28—C27—H27119.2
C12—C11—C13110.41 (18)C29—C28—C27121.2 (2)
C23—C11—C13111.63 (16)C29—C28—H28119.4
C10—C11—C13104.32 (16)C27—C28—H28119.4
N1—C12—C11179.7 (3)C28—C29—C30117.1 (2)
N2—C13—C20113.88 (18)C28—C29—H29121.5
N2—C13—C14113.76 (17)C30—C29—H29121.5
C20—C13—C14101.03 (17)N3—C30—C29129.1 (2)
N2—C13—C11102.17 (16)N3—C30—C25107.93 (19)
C20—C13—C11116.32 (17)C29—C30—C25123.0 (2)
C14—C13—C11110.14 (18)N3—C31—C24109.9 (2)
O1—C14—N4126.6 (2)N3—C31—H31125.1
O1—C14—C13126.2 (2)C24—C31—H31125.1
N4—C14—C13107.2 (2)C21—N2—C13107.89 (17)
C16—C15—C20122.2 (3)C21—N2—C22114.99 (19)
C16—C15—N4127.9 (2)C13—N2—C22114.23 (18)
C20—C15—N4109.9 (2)C31—N3—C30109.70 (19)
C17—C16—C15117.0 (3)C31—N3—H3A125.2
C17—C16—H16121.5C30—N3—H3A125.2
C15—C16—H16121.5C14—N4—C15112.2 (2)
C16—C17—C18122.1 (3)C14—N4—H4A123.9
C16—C17—H17118.9C15—N4—H4A123.9
C18—C17—H17118.9C1—O2—C2118.70 (17)
O2—C2—C3—C4177.9 (2)N4—C15—C20—C19174.1 (2)
C7—C2—C3—C42.2 (3)C16—C15—C20—C13177.2 (2)
C2—C3—C4—C50.3 (4)N4—C15—C20—C134.1 (3)
C3—C4—C5—C61.6 (4)N2—C13—C20—C1949.2 (3)
C4—C5—C6—C71.6 (4)C14—C13—C20—C19171.6 (3)
O2—C2—C7—C6177.87 (19)C11—C13—C20—C1969.2 (3)
C3—C2—C7—C62.1 (3)N2—C13—C20—C15128.8 (2)
O2—C2—C7—C82.4 (3)C14—C13—C20—C156.4 (2)
C3—C2—C7—C8177.6 (2)C11—C13—C20—C15112.8 (2)
C5—C6—C7—C20.2 (3)C9—C10—C21—N289.1 (2)
C5—C6—C7—C8179.5 (2)C11—C10—C21—N235.6 (2)
C2—C7—C8—O3175.6 (2)C12—C11—C23—O4135.8 (2)
C6—C7—C8—O34.1 (3)C10—C11—C23—O413.9 (3)
C2—C7—C8—C94.0 (3)C13—C11—C23—O4101.7 (2)
C6—C7—C8—C9176.31 (19)C12—C11—C23—C2447.7 (3)
O2—C1—C9—C80.8 (3)C10—C11—C23—C24169.53 (19)
O2—C1—C9—C10179.79 (19)C13—C11—C23—C2474.8 (2)
O3—C8—C9—C1176.4 (2)O4—C23—C24—C31177.3 (2)
C7—C8—C9—C13.2 (3)C11—C23—C24—C316.3 (4)
O3—C8—C9—C103.0 (3)O4—C23—C24—C254.6 (4)
C7—C8—C9—C10177.35 (17)C11—C23—C24—C25171.8 (2)
C1—C9—C10—C2118.8 (3)C31—C24—C25—C26178.7 (3)
C8—C9—C10—C21161.80 (19)C23—C24—C25—C262.8 (4)
C1—C9—C10—C11100.3 (2)C31—C24—C25—C301.0 (3)
C8—C9—C10—C1179.1 (2)C23—C24—C25—C30177.5 (2)
C9—C10—C11—C125.8 (3)C30—C25—C26—C270.2 (4)
C21—C10—C11—C12132.58 (19)C24—C25—C26—C27179.5 (3)
C9—C10—C11—C23127.01 (19)C25—C26—C27—C280.9 (4)
C21—C10—C11—C23106.2 (2)C26—C27—C28—C290.8 (5)
C9—C10—C11—C13112.85 (19)C27—C28—C29—C300.1 (4)
C21—C10—C11—C1313.9 (2)C28—C29—C30—N3178.7 (3)
C23—C11—C12—N1139 (100)C28—C29—C30—C250.6 (4)
C10—C11—C12—N199 (58)C26—C25—C30—N3178.9 (2)
C13—C11—C12—N116 (58)C24—C25—C30—N30.9 (3)
C12—C11—C13—N2106.58 (18)C26—C25—C30—C290.6 (4)
C23—C11—C13—N2131.55 (17)C24—C25—C30—C29179.6 (2)
C10—C11—C13—N212.2 (2)C25—C24—C31—N30.7 (3)
C12—C11—C13—C2018.1 (2)C23—C24—C31—N3177.7 (2)
C23—C11—C13—C20103.8 (2)C10—C21—N2—C1347.0 (2)
C10—C11—C13—C20136.82 (18)C10—C21—N2—C22175.8 (2)
C12—C11—C13—C14132.21 (18)C20—C13—N2—C21162.61 (19)
C23—C11—C13—C1410.3 (2)C14—C13—N2—C2182.3 (2)
C10—C11—C13—C14109.05 (18)C11—C13—N2—C2136.3 (2)
N2—C13—C14—O150.7 (3)C20—C13—N2—C2268.2 (3)
C20—C13—C14—O1173.2 (3)C14—C13—N2—C2246.9 (3)
C11—C13—C14—O163.3 (3)C11—C13—N2—C22165.5 (2)
N2—C13—C14—N4129.2 (2)C24—C31—N3—C300.2 (3)
C20—C13—C14—N46.7 (2)C29—C30—N3—C31179.9 (2)
C11—C13—C14—N4116.8 (2)C25—C30—N3—C310.5 (3)
C20—C15—C16—C173.2 (4)O1—C14—N4—C15175.1 (3)
N4—C15—C16—C17175.2 (3)C13—C14—N4—C154.9 (3)
C15—C16—C17—C180.2 (5)C16—C15—N4—C14177.9 (3)
C16—C17—C18—C192.2 (5)C20—C15—N4—C140.7 (3)
C17—C18—C19—C200.9 (4)C9—C1—O2—C21.0 (3)
C18—C19—C20—C152.3 (4)C7—C2—O2—C10.1 (3)
C18—C19—C20—C13179.9 (2)C3—C2—O2—C1179.87 (19)
C16—C15—C20—C194.5 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O4i0.862.142.967 (3)161
N4—H4A···O3ii0.862.062.866 (3)156
C29—H29···O2iii0.932.593.267 (3)131
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x+1/2, y+1/2, z+1/2; (iii) x, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O4i0.862.142.967 (3)161
N4—H4A···O3ii0.862.062.866 (3)156
C29—H29···O2iii0.932.593.267 (3)131
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x+1/2, y+1/2, z+1/2; (iii) x, y, z+1.
 

Acknowledgements

The authors thank thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for his help with the data collection.

References

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