4′-Amino-2,2′′-dioxo-2,2′′,3,3′′-tetra­hydro-1H-indole-3-spiro-1′-cyclo­pent-3′-ene-2′-spiro-3′′-1H-indole-3′,5′,5′-tricarbonitrile dihydrate

Gayathri, D.; Velmurugan, D.; Shanthi, G.; Perumal, P.T.; Ravikumar, K.

doi:10.1107/S1600536808002146

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 2| February 2008| Pages o501-o502

doi:10.1107/S1600536808002146

Open

access

4′-Amino-2,2′′-dioxo-2,2′′,3,3′′-tetrahydro-1H-indole-3-spiro-1′-cyclopent-3′-ene-2′-spiro-3′′-1H-indole-3′,5′,5′-tricarbonitrile dihydrate

D. Gayathri,^a D. Velmurugan,^a ^* G. Shanthi,^b P. T. Perumal ^b and K. Ravikumar ^c

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, ^bOrganic Chemistry Division, Central Leather Research Institute, Adyar, Chennai 600 020, India, and ^cLaboratory of X-ray Crystallography, Indian Institute of Chemical Technology, Hyderabad 500 007, India
^*Correspondence e-mail: d_velu@yahoo.com

(Received 10 December 2007; accepted 21 January 2008; online 23 January 2008)

In the title compound, C₂₂H₁₂N₆O₂·2H₂O, the cyclopentene ring adopts an envelope conformation, with the spiro C atom bonded to the dicyano-substituted C atom deviating by 0.437 (2) Å from the plane of the remaining four atoms in the ring. The puckering and smallest displacement asymmetry parameters for the ring are q₂ = 0.275 (2) Å, φ = 212.4 (4)° and Δ_s(C₂) = 2.7 (2). The dihedral angle between the two indole groups is 60.1 (1)°. The structure contains intermolecular N—H⋯O hydrogen bonds involving the indole groups and O—H⋯O and O—H⋯N hydrogen bonds involving the water molecules.

Related literature

For related literature, see: Akai et al. (2004 ); Cremer & Pople (1975 ); Gallagher et al. (1985 ); Nagata et al. (2001 ); Nardelli (1983 ); Williams & Cox (2003 ); Zaveri et al. (2004 ).

Experimental

Crystal data

C₂₂H₁₂N₆O₂·2H₂O
M_r = 428.41
Orthorhombic, P n a 2₁
a = 17.1850 (16) Å
b = 8.9849 (9) Å
c = 13.3275 (13) Å
V = 2057.8 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 (2) K
0.25 × 0.24 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: none
16968 measured reflections
2551 independent reflections
2367 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.108
S = 1.06
2551 reflections
313 parameters
9 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ⁱ	0.86	2.09	2.905 (2)	158
N2—H2⋯O3ⁱ	0.86	2.22	3.032 (3)	157
O3—H3A⋯O1ⁱⁱ	0.85 (1)	2.00 (2)	2.795 (3)	157 (4)
O3—H3B⋯N6ⁱⁱⁱ	0.85 (1)	2.22 (5)	2.834 (3)	129 (5)
O3—H3B⋯O4^iv	0.85 (1)	2.62 (3)	3.381 (4)	149 (5)
O4—H4A⋯N4^v	0.85 (1)	2.38 (3)	3.171 (5)	155 (7)
O4—H4B⋯N3	0.85 (1)	2.68 (4)	3.392 (4)	142 (6)
N5—H5A⋯O3^vi	0.90 (1)	1.97 (1)	2.860 (3)	175 (3)
N5—H5B⋯O4^vi	0.90 (1)	2.17 (1)	3.061 (4)	171 (3)
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x, y+1, z+1; (iii) x, y, z+1; (iv) $[-x, -y+1, z+{\script{1\over 2}}]$ ; (v) $[-x, -y, z+{\script{1\over 2}}]$ ; (vi) $[-x, -y+1, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808002146/bi2273sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808002146/bi2273Isup2.hkl

checkCIF report

Comment top

The indole template is generally recognized as an important structure in medicinal chemistry, and in particular, oxindoles are important constituents of natural indole alkaloids as well as drugs in development and also in the clinic (Akai et al., 2004). Among them, the spiro-oxindole framework is an important structural motif in biologically relevant compounds such as natural products and pharmaceuticals (Williams & Cox, 2003). The oxindole motif is present in the anti-Parkinson's drug ropinirole (Gallagher et al., 1985), in non-opioid nociceptin receptor ligands (Zaveri et al., 2004), and in the growth hormone secretagogues (Nagata et al., 2001). As the title compound is biologically important, we have determined its crystal structure using X-ray diffraction.

One of the oxindole moieties (C2/C13/N2/C14/C19) is planar with atom O2 deviating by 0.127 (1) Å from the plane of five-membered ring. The dihedral angle between the five- (C2/C13/N2/C14/C19) and six-membered (C14—C19) rings is 1.6 (1)°. The cyclopentene ring adopts an envelope conformation with C2 deviating by 0.437 (2) Å from the plane of the rest of the atoms in the ring. The five-membered ring (N1/C6/C1/C12/C7) in the oxindole moieties adopts a slightly twisted conformation. The puckering parameters (Cremer & Pople, 1975) and the smallest displacement asymmetry parameters (Nardelli, 1983) for the cyclopentene ring and the five-membered ring (N1/C6/C1/C12/C7) are q₂ = 0.275 (2)Å and 0.091 (2) Å, ϕ = 212.4 (4)° and 56.3 (12)° and Δ_s(C₂) = 2.7 (2) and Δ₂(C₇) = 0.5 (2), respectively.

Related literature top

For related literature, see: Akai et al. (2004); Cremer & Pople (1975); Gallagher et al. (1985); Nagata et al. (2001); Nardelli (1983); Williams & Cox (2003); Zaveri et al. (2004).

Experimental top

To a stirred mixture of isatylidene malononitrile (2 mmol) and Hantzsch dihydropyridine ester (1 mmol) in ethanol (10 ml), a catalytic amount of indium(III) chloride (20 mol%) was added and the mixture was stirred at room temperature for about 1–2 h. After complete conversion (as indicated by TLC), the reaction mixture was poured into water and extracted with ethyl acetate (2 × 15 ml). The combined extracts were dried over anhydrous Na₂SO₄ and concentrated in vacuo. The resulting product was purified by column chromatography on silica gel (Merck, 60–120 mesh, ethyl acetate-hexane, 4:6) to afford the pure product in 88% yield as a white solid. Crystals were grown by slow evaporation from ethanol.

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: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PARST (Nardelli, 1995).

Figures top

	Fig. 1. The molecular structure of title compound, showing 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The molecular packing viewed down the a axis, showing O—H···N and O—H···O intermolecular interactions.
	Fig. 3. The molecular packing viewed down the a axis, showing N—H···O intermolecular interactions.

4'-Amino-2,2''-dioxo-2,2'',3,3''-tetrahydro-1H-indole-3-spiro-1'-cyclopent- 3'-ene-2'-spiro-3''-1H-indole-3',5',5'-tricarbonitrile dihydrate top

Crystal data top

C₂₂H₁₂N₆O₂·2H₂O	F(000) = 888
M_r = 428.41	D_x = 1.383 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2386 reflections
a = 17.1850 (16) Å	θ = 2.4–28.0°
b = 8.9849 (9) Å	µ = 0.10 mm⁻¹
c = 13.3275 (13) Å	T = 293 K
V = 2057.8 (3) Å³	Block, colorless
Z = 4	0.25 × 0.24 × 0.20 mm

Data collection top

Bruker SMART APEX CCD diffractometer	2367 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.022
Graphite monochromator	θ_max = 28.0°, θ_min = 2.4°
ω scans	h = −22→22
16968 measured reflections	k = −11→11
2551 independent reflections	l = −17→17

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0751P)² + 0.1068P] where P = (F_o² + 2F_c²)/3
2551 reflections	(Δ/σ)_max < 0.001
313 parameters	Δρ_max = 0.27 e Å⁻³
9 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₂₂H₁₂N₆O₂·2H₂O	V = 2057.8 (3) Å³
M_r = 428.41	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 17.1850 (16) Å	µ = 0.10 mm⁻¹
b = 8.9849 (9) Å	T = 293 K
c = 13.3275 (13) Å	0.25 × 0.24 × 0.20 mm

Data collection top

Bruker SMART APEX CCD diffractometer	2367 reflections with I > 2σ(I)
16968 measured reflections	R_int = 0.022
2551 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	9 restraints
wR(F²) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.27 e Å⁻³
2551 reflections	Δρ_min = −0.14 e Å⁻³
313 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

	x	y	z	U_iso*/U_eq
C1	0.19406 (12)	0.1506 (2)	0.03645 (16)	0.0341 (4)
C2	0.19661 (11)	0.0810 (2)	0.14549 (15)	0.0320 (4)
C3	0.11505 (12)	0.1206 (2)	0.19253 (16)	0.0352 (4)
C4	0.09089 (12)	0.2598 (2)	0.13339 (17)	0.0349 (4)
C5	0.13624 (13)	0.2738 (2)	0.05081 (16)	0.0354 (4)
C6	0.16280 (14)	0.0331 (2)	−0.03919 (16)	0.0414 (5)
C7	0.28704 (15)	0.0835 (3)	−0.08495 (19)	0.0452 (5)
C8	0.35505 (18)	0.0831 (4)	−0.1392 (2)	0.0614 (7)
H8A	0.3636	0.0143	−0.1902	0.074*
C9	0.41025 (19)	0.1889 (4)	−0.1150 (3)	0.0679 (8)
H9A	0.4570	0.1906	−0.1501	0.082*
C10	0.39785 (17)	0.2922 (4)	−0.0399 (3)	0.0612 (7)
H10A	0.4358	0.3629	−0.0256	0.073*
C11	0.32867 (16)	0.2907 (3)	0.0144 (2)	0.0489 (6)
H11A	0.3198	0.3607	0.0645	0.059*
C12	0.27339 (13)	0.1839 (2)	−0.00708 (16)	0.0375 (4)
C13	0.25886 (12)	0.1685 (2)	0.20696 (15)	0.0340 (4)
C14	0.29683 (12)	−0.0747 (2)	0.20308 (17)	0.0378 (4)
C15	0.34057 (15)	−0.2019 (3)	0.2170 (2)	0.0493 (6)
H15A	0.3882	−0.1992	0.2501	0.059*
C16	0.31063 (17)	−0.3336 (3)	0.1795 (2)	0.0564 (7)
H16A	0.3388	−0.4211	0.1878	0.068*
C17	0.24070 (18)	−0.3388 (3)	0.1305 (2)	0.0581 (7)
H17A	0.2221	−0.4293	0.1065	0.070*
C18	0.19709 (16)	−0.2097 (2)	0.1161 (2)	0.0489 (6)
H18A	0.1497	−0.2129	0.0824	0.059*
C19	0.22569 (13)	−0.0769 (2)	0.15289 (16)	0.0364 (4)
C20	0.12114 (15)	0.1500 (3)	0.30204 (19)	0.0449 (5)
C21	0.05602 (14)	0.0018 (3)	0.1798 (2)	0.0470 (5)
C22	0.12327 (16)	0.3857 (3)	−0.0210 (2)	0.0506 (6)
N1	0.22129 (14)	−0.0067 (2)	−0.09965 (16)	0.0486 (5)
H1	0.2189	−0.0785	−0.1422	0.058*
N2	0.31446 (11)	0.0717 (2)	0.23268 (15)	0.0413 (4)
H2	0.3564	0.0962	0.2639	0.050*
N3	0.12535 (18)	0.1713 (4)	0.38515 (19)	0.0706 (7)
N4	0.01054 (15)	−0.0884 (3)	0.1731 (3)	0.0727 (8)
N5	0.03222 (13)	0.3429 (3)	0.16605 (18)	0.0498 (5)
H5A	0.0025 (15)	0.311 (3)	0.2169 (17)	0.048 (7)*
H5B	0.011 (2)	0.417 (3)	0.130 (3)	0.070 (10)*
N6	0.1106 (2)	0.4754 (4)	−0.0785 (3)	0.0916 (11)
O1	0.09597 (11)	−0.0125 (2)	−0.04096 (16)	0.0567 (5)
O2	0.25526 (10)	0.29951 (16)	0.22853 (13)	0.0429 (4)
O3	0.05768 (12)	0.7461 (2)	0.83632 (15)	0.0540 (4)
H3A	0.073 (3)	0.830 (3)	0.858 (3)	0.107 (15)*
H3B	0.054 (4)	0.692 (4)	0.888 (2)	0.15 (2)*
O4	0.0238 (2)	0.3832 (4)	0.5501 (3)	0.0938 (9)
H4A	0.020 (4)	0.322 (6)	0.599 (4)	0.16 (3)*
H4B	0.066 (2)	0.360 (6)	0.521 (4)	0.13 (2)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0439 (10)	0.0289 (9)	0.0294 (9)	0.0008 (8)	−0.0003 (8)	−0.0036 (7)
C2	0.0387 (9)	0.0268 (9)	0.0304 (9)	−0.0010 (7)	−0.0022 (8)	−0.0033 (7)
C3	0.0384 (9)	0.0334 (9)	0.0338 (10)	−0.0009 (8)	0.0006 (8)	0.0015 (8)
C4	0.0404 (10)	0.0319 (9)	0.0325 (9)	−0.0002 (7)	−0.0024 (8)	−0.0019 (8)
C5	0.0428 (10)	0.0329 (10)	0.0305 (9)	0.0024 (8)	−0.0017 (8)	−0.0015 (8)
C6	0.0565 (13)	0.0354 (10)	0.0324 (10)	0.0013 (9)	−0.0081 (10)	−0.0082 (8)
C7	0.0582 (13)	0.0408 (11)	0.0367 (11)	0.0131 (10)	0.0031 (10)	−0.0020 (9)
C8	0.0700 (18)	0.0639 (17)	0.0503 (15)	0.0182 (13)	0.0193 (14)	−0.0015 (13)
C9	0.0570 (16)	0.083 (2)	0.0642 (18)	0.0135 (15)	0.0240 (14)	0.0145 (17)
C10	0.0539 (15)	0.0616 (16)	0.0682 (19)	−0.0052 (12)	0.0088 (14)	0.0140 (14)
C11	0.0552 (14)	0.0411 (12)	0.0504 (14)	−0.0037 (10)	0.0070 (11)	−0.0017 (10)
C12	0.0449 (11)	0.0353 (10)	0.0321 (10)	0.0060 (8)	0.0030 (9)	0.0003 (8)
C13	0.0407 (9)	0.0341 (9)	0.0271 (9)	−0.0040 (8)	0.0010 (8)	−0.0036 (7)
C14	0.0443 (10)	0.0351 (10)	0.0340 (10)	0.0029 (8)	0.0020 (9)	−0.0012 (8)
C15	0.0517 (13)	0.0486 (13)	0.0476 (13)	0.0143 (10)	0.0002 (11)	0.0010 (11)
C16	0.0687 (16)	0.0374 (11)	0.0632 (16)	0.0167 (11)	0.0081 (13)	0.0036 (11)
C17	0.0764 (18)	0.0286 (11)	0.0692 (18)	0.0006 (11)	0.0009 (14)	−0.0073 (11)
C18	0.0586 (14)	0.0320 (10)	0.0563 (14)	−0.0015 (9)	−0.0054 (12)	−0.0061 (10)
C19	0.0443 (10)	0.0300 (9)	0.0351 (10)	0.0021 (8)	0.0006 (9)	−0.0004 (8)
C20	0.0473 (12)	0.0483 (12)	0.0392 (13)	0.0044 (10)	0.0049 (10)	0.0056 (10)
C21	0.0447 (11)	0.0433 (12)	0.0530 (14)	−0.0024 (10)	−0.0003 (11)	0.0055 (10)
C22	0.0640 (15)	0.0478 (12)	0.0400 (12)	0.0167 (11)	0.0151 (11)	0.0054 (10)
N1	0.0696 (13)	0.0394 (10)	0.0368 (10)	0.0049 (9)	−0.0004 (10)	−0.0135 (8)
N2	0.0418 (9)	0.0414 (9)	0.0406 (10)	0.0006 (7)	−0.0076 (8)	−0.0047 (8)
N3	0.0812 (18)	0.0944 (19)	0.0363 (13)	0.0063 (14)	0.0041 (11)	0.0020 (12)
N4	0.0595 (13)	0.0613 (14)	0.097 (2)	−0.0217 (12)	−0.0013 (14)	0.0057 (15)
N5	0.0509 (11)	0.0526 (12)	0.0458 (11)	0.0136 (9)	0.0108 (10)	0.0073 (9)
N6	0.121 (3)	0.084 (2)	0.0696 (18)	0.0470 (19)	0.0373 (18)	0.0380 (16)
O1	0.0578 (11)	0.0560 (10)	0.0563 (11)	−0.0089 (8)	−0.0123 (9)	−0.0163 (9)
O2	0.0552 (9)	0.0330 (7)	0.0404 (8)	−0.0026 (6)	−0.0050 (7)	−0.0110 (6)
O3	0.0606 (11)	0.0517 (9)	0.0498 (10)	0.0029 (9)	−0.0094 (9)	−0.0077 (8)
O4	0.093 (2)	0.091 (2)	0.097 (2)	0.0319 (15)	−0.0022 (16)	0.0075 (18)

Geometric parameters (Å, º) top

C1—C5	1.500 (3)	C11—H11A	0.930
C1—C12	1.511 (3)	C13—O2	1.213 (3)
C1—C6	1.556 (3)	C13—N2	1.337 (3)
C1—C2	1.583 (3)	C14—C15	1.380 (3)
C2—C19	1.508 (3)	C14—C19	1.394 (3)
C2—C13	1.560 (3)	C14—N2	1.406 (3)
C2—C3	1.576 (3)	C15—C16	1.384 (4)
C3—C21	1.482 (3)	C15—H15A	0.930
C3—C20	1.487 (3)	C16—C17	1.369 (4)
C3—C4	1.535 (3)	C16—H16A	0.930
C4—N5	1.328 (3)	C17—C18	1.394 (4)
C4—C5	1.354 (3)	C17—H17A	0.930
C5—C22	1.406 (3)	C18—C19	1.380 (3)
C6—O1	1.220 (3)	C18—H18A	0.930
C6—N1	1.337 (3)	C20—N3	1.126 (4)
C7—C8	1.374 (4)	C21—N4	1.130 (3)
C7—C12	1.395 (3)	C22—N6	1.133 (4)
C7—N1	1.404 (3)	N1—H1	0.860
C8—C9	1.381 (5)	N2—H2	0.860
C8—H8A	0.930	N5—H5A	0.90 (1)
C9—C10	1.382 (5)	N5—H5B	0.90 (1)
C9—H9A	0.930	O3—H3A	0.85 (1)
C10—C11	1.392 (4)	O3—H3B	0.85 (1)
C10—H10A	0.930	O4—H4A	0.85 (1)
C11—C12	1.380 (3)	O4—H4B	0.85 (1)

C5—C1—C12	120.04 (17)	C12—C11—H11A	120.4
C5—C1—C6	110.78 (17)	C10—C11—H11A	120.4
C12—C1—C6	101.37 (17)	C11—C12—C7	119.2 (2)
C5—C1—C2	101.12 (16)	C11—C12—C1	132.7 (2)
C12—C1—C2	113.93 (17)	C7—C12—C1	108.0 (2)
C6—C1—C2	109.64 (16)	O2—C13—N2	127.39 (19)
C19—C2—C13	102.28 (17)	O2—C13—C2	125.34 (19)
C19—C2—C3	118.76 (17)	N2—C13—C2	107.25 (16)
C13—C2—C3	106.69 (16)	C15—C14—C19	122.0 (2)
C19—C2—C1	116.18 (17)	C15—C14—N2	128.3 (2)
C13—C2—C1	107.57 (15)	C19—C14—N2	109.72 (18)
C3—C2—C1	104.56 (15)	C14—C15—C16	117.2 (2)
C21—C3—C20	106.75 (19)	C14—C15—H15A	121.4
C21—C3—C4	110.04 (18)	C16—C15—H15A	121.4
C20—C3—C4	112.24 (19)	C17—C16—C15	121.9 (2)
C21—C3—C2	113.62 (17)	C17—C16—H16A	119.1
C20—C3—C2	111.58 (18)	C15—C16—H16A	119.1
C4—C3—C2	102.72 (16)	C16—C17—C18	120.6 (2)
N5—C4—C5	130.6 (2)	C16—C17—H17A	119.7
N5—C4—C3	119.7 (2)	C18—C17—H17A	119.7
C5—C4—C3	109.72 (18)	C19—C18—C17	118.6 (3)
C4—C5—C22	121.9 (2)	C19—C18—H18A	120.7
C4—C5—C1	114.59 (18)	C17—C18—H18A	120.7
C22—C5—C1	123.10 (19)	C18—C19—C14	119.7 (2)
O1—C6—N1	127.3 (2)	C18—C19—C2	132.2 (2)
O1—C6—C1	124.5 (2)	C14—C19—C2	107.96 (18)
N1—C6—C1	108.2 (2)	N3—C20—C3	179.4 (3)
C8—C7—C12	122.4 (3)	N4—C21—C3	178.0 (3)
C8—C7—N1	127.5 (2)	N6—C22—C5	178.1 (3)
C12—C7—N1	110.0 (2)	C6—N1—C7	111.51 (19)
C7—C8—C9	117.3 (3)	C6—N1—H1	124.2
C7—C8—H8A	121.3	C7—N1—H1	124.2
C9—C8—H8A	121.3	C13—N2—C14	112.51 (18)
C8—C9—C10	121.7 (3)	C13—N2—H2	123.7
C8—C9—H9A	119.1	C14—N2—H2	123.7
C10—C9—H9A	119.1	C4—N5—H5A	119.9 (19)
C9—C10—C11	120.1 (3)	C4—N5—H5B	123 (3)
C9—C10—H10A	119.9	H5A—N5—H5B	115 (3)
C11—C10—H10A	119.9	H3A—O3—H3B	105.1 (17)
C12—C11—C10	119.1 (2)	H4A—O4—H4B	104.8 (17)

C5—C1—C2—C19	158.77 (17)	C9—C10—C11—C12	0.7 (4)
C12—C1—C2—C19	−71.0 (2)	C10—C11—C12—C7	−2.2 (4)
C6—C1—C2—C19	41.8 (2)	C10—C11—C12—C1	179.7 (2)
C5—C1—C2—C13	−87.37 (18)	C8—C7—C12—C11	2.5 (4)
C12—C1—C2—C13	42.8 (2)	N1—C7—C12—C11	−175.0 (2)
C6—C1—C2—C13	155.61 (17)	C8—C7—C12—C1	−179.0 (2)
C5—C1—C2—C3	25.79 (18)	N1—C7—C12—C1	3.5 (3)
C12—C1—C2—C3	155.99 (17)	C5—C1—C12—C11	48.3 (4)
C6—C1—C2—C3	−91.22 (18)	C6—C1—C12—C11	170.6 (2)
C19—C2—C3—C21	−37.6 (3)	C2—C1—C12—C11	−71.8 (3)
C13—C2—C3—C21	−152.32 (18)	C5—C1—C12—C7	−130.0 (2)
C1—C2—C3—C21	93.88 (19)	C6—C1—C12—C7	−7.7 (2)
C19—C2—C3—C20	83.1 (2)	C2—C1—C12—C7	110.0 (2)
C13—C2—C3—C20	−31.6 (2)	C19—C2—C13—O2	−173.2 (2)
C1—C2—C3—C20	−145.38 (18)	C3—C2—C13—O2	−47.8 (3)
C19—C2—C3—C4	−156.44 (18)	C1—C2—C13—O2	63.9 (3)
C13—C2—C3—C4	88.85 (18)	C19—C2—C13—N2	5.2 (2)
C1—C2—C3—C4	−24.95 (19)	C3—C2—C13—N2	130.60 (18)
C21—C3—C4—N5	72.4 (3)	C1—C2—C13—N2	−117.67 (18)
C20—C3—C4—N5	−46.3 (3)	C19—C14—C15—C16	−0.5 (4)
C2—C3—C4—N5	−166.3 (2)	N2—C14—C15—C16	−179.2 (2)
C21—C3—C4—C5	−106.6 (2)	C14—C15—C16—C17	0.1 (4)
C20—C3—C4—C5	134.7 (2)	C15—C16—C17—C18	0.4 (5)
C2—C3—C4—C5	14.7 (2)	C16—C17—C18—C19	−0.4 (5)
N5—C4—C5—C22	−3.5 (4)	C17—C18—C19—C14	0.0 (4)
C3—C4—C5—C22	175.3 (2)	C17—C18—C19—C2	175.9 (3)
N5—C4—C5—C1	−176.4 (2)	C15—C14—C19—C18	0.4 (4)
C3—C4—C5—C1	2.4 (3)	N2—C14—C19—C18	179.4 (2)
C12—C1—C5—C4	−144.5 (2)	C15—C14—C19—C2	−176.4 (2)
C6—C1—C5—C4	97.9 (2)	N2—C14—C19—C2	2.6 (3)
C2—C1—C5—C4	−18.3 (2)	C13—C2—C19—C18	179.1 (3)
C12—C1—C5—C22	42.7 (3)	C3—C2—C19—C18	62.1 (4)
C6—C1—C5—C22	−74.9 (3)	C1—C2—C19—C18	−64.0 (3)
C2—C1—C5—C22	168.9 (2)	C13—C2—C19—C14	−4.6 (2)
C5—C1—C6—O1	−41.8 (3)	C3—C2—C19—C14	−121.6 (2)
C12—C1—C6—O1	−170.3 (2)	C1—C2—C19—C14	112.2 (2)
C2—C1—C6—O1	68.9 (3)	O1—C6—N1—C7	171.7 (2)
C5—C1—C6—N1	138.14 (19)	C1—C6—N1—C7	−8.3 (3)
C12—C1—C6—N1	9.6 (2)	C8—C7—N1—C6	−174.1 (3)
C2—C1—C6—N1	−111.1 (2)	C12—C7—N1—C6	3.2 (3)
C12—C7—C8—C9	−1.1 (4)	O2—C13—N2—C14	174.4 (2)
N1—C7—C8—C9	176.0 (3)	C2—C13—N2—C14	−4.0 (2)
C7—C8—C9—C10	−0.5 (5)	C15—C14—N2—C13	179.9 (2)
C8—C9—C10—C11	0.7 (5)	C19—C14—N2—C13	1.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.86	2.09	2.905 (2)	158
N2—H2···O3ⁱ	0.86	2.22	3.032 (3)	157
O3—H3A···O1ⁱⁱ	0.85 (1)	2.00 (2)	2.795 (3)	157 (4)
O3—H3B···N6ⁱⁱⁱ	0.85 (1)	2.22 (5)	2.834 (3)	129 (5)
O3—H3B···O4^iv	0.85 (1)	2.62 (3)	3.381 (4)	149 (5)
O4—H4A···N4^v	0.85 (1)	2.38 (3)	3.171 (5)	155 (7)
O4—H4B···N3	0.85 (1)	2.68 (4)	3.392 (4)	142 (6)
N5—H5A···O3^vi	0.90 (1)	1.97 (1)	2.860 (3)	175 (3)
N5—H5B···O4^vi	0.90 (1)	2.17 (1)	3.061 (4)	171 (3)

Symmetry codes: (i) −x+1/2, y−1/2, z−1/2; (ii) x, y+1, z+1; (iii) x, y, z+1; (iv) −x, −y+1, z+1/2; (v) −x, −y, z+1/2; (vi) −x, −y+1, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₂N₆O₂·2H₂O
M_r	428.41
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	293
a, b, c (Å)	17.1850 (16), 8.9849 (9), 13.3275 (13)
V (Å³)	2057.8 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.25 × 0.24 × 0.20

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	16968, 2551, 2367
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.660

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.108, 1.06
No. of reflections	2551
No. of parameters	313
No. of restraints	9
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.14

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), PLATON (Spek, 2003), SHELXL97 (Sheldrick, 2008) and PARST (Nardelli, 1995).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.86	2.09	2.905 (2)	158.0
N2—H2···O3ⁱ	0.86	2.22	3.032 (3)	157.3
O3—H3A···O1ⁱⁱ	0.85 (1)	2.00 (2)	2.795 (3)	157 (4)
O3—H3B···N6ⁱⁱⁱ	0.85 (1)	2.22 (5)	2.834 (3)	129 (5)
O3—H3B···O4^iv	0.85 (1)	2.62 (3)	3.381 (4)	149 (5)
O4—H4A···N4^v	0.85 (1)	2.38 (3)	3.171 (5)	155 (7)
O4—H4B···N3	0.85 (1)	2.68 (4)	3.392 (4)	142 (6)
N5—H5A···O3^vi	0.90 (1)	1.97 (1)	2.860 (3)	175 (3)
N5—H5B···O4^vi	0.90 (1)	2.17 (1)	3.061 (4)	171 (3)

Symmetry codes: (i) −x+1/2, y−1/2, z−1/2; (ii) x, y+1, z+1; (iii) x, y, z+1; (iv) −x, −y+1, z+1/2; (v) −x, −y, z+1/2; (vi) −x, −y+1, z−1/2.

Acknowledgements

DG thanks the Council of Scientific and Industrial Research (CSIR), India, for a Senior Research Fellowship. Financial support from the University Grants Commission (UGC–SAP) and Department of Science and Technology (DST–FIST), Government of India, is acknowledged by DV for providing facilities to the department.

References

Akai, S., Tsujino, T., Akiyama, E., Tanimoto, K., Naka, T. & Kita, Y. (2004). J. Org. Chem. 69, 2478–2486. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2001). SMART (Version. 5.625/NT/2000) and SAINT (Version 6.28a). Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Gallagher, G., Lavanchi, P. G., Wilson, J. W., Hieble, J. & Demmarinis, R. M. (1985). J. Med. Chem. 28, 1533–1536. CrossRef CAS PubMed Web of Science Google Scholar
Nagata, R., Tokunaga, T., Hume, W., Umezone, T., Okazaki, U., Ueki, Y., Kumagai, K., Hourai, S., Nagamine, J., Seki, H., Taiji, M. & Noguchi, H. (2001). J. Med. Chem. 44, 4641–4649. Web of Science PubMed Google Scholar
Nardelli, M. (1983). Acta Cryst. C39, 1141–1142. CrossRef CAS Web of Science IUCr Journals Google Scholar
Nardelli, M. (1995). J. Appl. Cryst. 28, 659. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Williams, R. M. & Cox, R. (2003). Acc. Chem. Res. 36, 127–139. Web of Science CrossRef PubMed CAS Google Scholar
Zaveri, N. T., Jiang, F., Olsen, C. M., Deschamps, J. R., Parrish, D., Polgar, W. & Toll, L. (2004). J. Med. Chem. 47, 2973–2976. Web of Science CSD CrossRef PubMed CAS Google Scholar

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.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 2| February 2008| Pages o501-o502

doi:10.1107/S1600536808002146

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

4′-Amino-2,2′′-dioxo-2,2′′,3,3′′-tetra­hydro-1H-indole-3-spiro-1′-cyclo­pent-3′-ene-2′-spiro-3′′-1H-indole-3′,5′,5′-tricarbo­nitrile dihydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4′-Amino-2,2′′-dioxo-2,2′′,3,3′′-tetrahydro-1H-indole-3-spiro-1′-cyclopent-3′-ene-2′-spiro-3′′-1H-indole-3′,5′,5′-tricarbonitrile dihydrate