3-(2-Amino-1-methyl-4-oxo-4,5-dihydro-1H-imidazol-5-yl)-3-hydroxy­indolin-2-one monohydrate

Penthala, N.R.; Reddy, T.R.Y.; Parkin, S.; Crooks, P.A.

doi:10.1107/S1600536809004875

organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o552

doi:10.1107/S1600536809004875

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3-(2-Amino-1-methyl-4-oxo-4,5-dihydro-1H-imidazol-5-yl)-3-hydroxyindolin-2-one monohydrate

Narsimha Reddy Penthala,^a Thirupathi Reddy Yerram Reddy,^a Sean Parkin ^b and Peter A. Crooks ^a ^*

^aDepartment of Pharmaceutical Sciences, College of Pharmacy, University of Kentucky, Lexington, KY 40536, USA, and ^bDepartment of Chemistry, University of Kentucky, Lexington, KY 40506, USA
^*Correspondence e-mail: pcrooks@email.uky.edu

(Received 3 February 2009; accepted 10 February 2009; online 21 February 2009)

Two chiral centres exist in the title compound, C₁₂H₁₂N₄O₃·H₂O. Molecules are linked into chains by series of intermolecular N—H⋯O and O—H⋯N hydrogen bonds, which causes supramolecular aggregation. Two chiral centres are formed in the title compound. The indole and creatinine moieties make a dihedral angle of 56.75 (4)°. The crystal structure of the compound indicates the presence of equimolar enantiomers (RR and SS) in the crystal structure.

Related literature

For 2-indol-3-yl-methylenequinuclidin-3-ols NADPH oxidase activity, see: Sekhar et al. (2003 ). For novel substituted (Z)-2-(N-benzylindol-3-ylmethylene)quinuclidin-3-one and (Z)-(±)-2-(N-benzylindol-3-ylmethylene)quinuclidin-3-ol derivatives as potent thermal sensitizing agents, see: Sonar et al. (2007 ). For the crystal and molecular structure of isatin, see: Frolova et al. (1988 ). For the structure of 1,1′-diacetyl-3-hydroxy-2,2′,3,3′-tetrahydro-3,3′-bi(1H-indole)-2,2′-dione, see: Usman et al. (2002 ). The aldol condensation enolate mechanism by six-membered transition states has been described by Zimmerman & Traxler (1957 ).

Experimental

Crystal data

C₁₂H₁₂N₄O₃·H₂O
M_r = 278.27
Monoclinic, P 2₁ /n
a = 8.3514 (1) Å
b = 10.7166 (2) Å
c = 13.9679 (2) Å
β = 104.755 (1)°
V = 1208.88 (3) Å³
Z = 4
Cu Kα radiation
μ = 0.99 mm⁻¹
T = 90 K
0.20 × 0.15 × 0.06 mm

Data collection

Bruker X8 Proteum diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2006 ) T_min = 0.780, T_max = 0.943
17255 measured reflections
2181 independent reflections
2121 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.088
S = 1.04
2181 reflections
191 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1Wⁱ	0.88	1.96	2.8128 (15)	163
O8—H8⋯N12ⁱⁱ	0.84	1.97	2.7984 (14)	170
N11—H11A⋯O13ⁱⁱⁱ	0.88	2.17	3.0371 (15)	171
N11—H11B⋯O1^iv	0.88	2.13	2.8678 (15)	141
O1W—H1W⋯O8	0.847 (18)	2.049 (18)	2.8812 (14)	167.4 (19)
O1W—H2W⋯O13^v	0.861 (18)	2.233 (18)	3.0702 (14)	164.1 (19)
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) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2006); cell refinement: APEX2 and SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 and local procedures.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809004875/hg2475sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809004875/hg2475Isup2.hkl

checkCIF report

Comment top

In our endeavor to design and synthesize novel radiosensitizers such as (Z)-2-(N-benzylindol-3-ylmethylene)quinuclidin-3-one and (Z)-(±)-2-(N-benzylindol-3-ylmethylene)quinuclidin-3-ol derivatives (Sekhar et al., 2003; Sonar et al., 2007), we have undertaken the design, synthesis and structural analysis of a series of 3-(2-amino-1-methyl-4-oxo-4,5-dihydro-1H-imidazol-5-yl)-3- hydroxyindolin-2-one analogs with different substituents on the indole moiety. The primary goal for X-ray analysis of the title compound is to confirm the stereochemistry of the molecule and to obtain detailed information on the structural conformation that may be useful in structure–activity relationship (SAR) analysis. The title compound was prepared by the aldol condensation of indol-2,3-dione (isatin) with 2-amino-1-methyl-1H-imidazol-4(5H)-one (creatinine) in the presence of sodium acetate in acetic acid under microwave irradiation. The compound was crystallized from 2% aqueous glycol. This aldol condensation reaction proceeds by the formation of the E-enolate, as per the Zimmerman–Traxler model (Zimmerman & Traxler, 1957), which favors anti products, and leads to the formation of equimolar RR and SS enantiomers. The molecular structure and the atom-numbering scheme are shown in Fig. 1. The isatin ring is planar (r.m.s. deviation = 0.0112 (10) Å) with bond distances and angles comparable with those previously reported for other isatin derivatives (Frolova et al., 1988; Usman et al., 2002). Atoms C₈ and C₉ are the two chiral centers of the title compound. The X-ray studies revealed that the obtained compound is racemic (having equimolar RR and SS enantiomers). The indole and creatinine moieties make a dihedral angle of 56.75 (4)°. Intermolecular N—H···O and O—H···N hydrogen bonds stabilize the crystal structure and form a supramolecular architecture.

Related literature top

For 2-indol-3-yl-methylenequinuclidin-3-ols NADPH oxidase activity, see: Sekhar et al. (2003). For novel substituted (Z)-2-(N-benzylindol-3-ylmethylene)quinuclidin-3-one and (Z)-(±)-2-(N-benzylindol-3-ylmethylene)quinuclidin-3-ol derivatives as potent thermal sensitizing agents, see: Sonar et al. (2007). For the crystal and molecular structure of isatin, see: Frolova et al. (1988). For the structure of 1,1'-diacetyl-3-hydroxy-2,2',3,3'- tetrahydro-3,3'-bi(1H-indole)-2,2'-dione, see: Usman et al. (2002). The aldol condensation enolate mechanism by six-membered transition states has been described by Zimmerman & Traxler (1957).

Experimental top

A mixture of isatin (1 mmol), creatinine (1.1 mmol) and sodium acetate (1.2 mmol) in acetic acid (1 ml) were irradiated in a domestic microwave oven for 40 sec with intermittent cooling every 10 sec. The reaction mixture was allowed to cool to room temperature, 10 ml of saturated sodium bicarbonate solution was added, and the mixture was stirred for 10 minutes. The precipitate thus obtained was collected by filtration, washed with cold water and dried, to afford the crude product. Crystallization from 2% aqueous glycol gave a light yellow crystalline product of 3-(2-amino-1-methyl-4-oxo-4,5-dihydro-1H- imidazol-5-yl)-3-hydroxyindolin-2-one monohydrate that was suitable for X-ray analysis. ¹H NMR (DMSO-d₆): δ 3.13 (s, 3H), 4.06 (s, 1H), 6.37 (s, 1H, OH), 6.73–6.75 (d, J = 7.5 Hz, 1H), 6.84–6.89 (t, J = 7.5 Hz, 1H), 7.04–7.06 (d, J = 7.5 Hz, 1H), 7.15–7.21 (t, J = 7.8 Hz, 1H), 7.51 (bs, 2H, NH₂), 10.23 (s, 1H, NH) p.p.m.; ¹³C NMR (DMSO-d₆): δ 32.59, 69.44, 76.28, 109.49, 121.1, 123.95, 127.98,129.34, 142.66, 171.76, 175.71, 182.26 p.p.m.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: APEX2 (Bruker, 2006); data reduction: APEX2 (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and local procedures.

Figures top

Fig. 1. A view of the molecule with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

3-(2-Amino-1-methyl-4-oxo-4,5-dihydro-1H-imidazol-5-yl)-3- hydroxyindolin-2-one monohydrate top

Crystal data top

C₁₂H₁₂N₄O₃·H₂O	F(000) = 584
M_r = 278.27	D_x = 1.529 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2yn	Cell parameters from 9952 reflections
a = 8.3514 (1) Å	θ = 5.3–68.0°
b = 10.7166 (2) Å	µ = 0.99 mm⁻¹
c = 13.9679 (2) Å	T = 90 K
β = 104.755 (1)°	Block, colourless
V = 1208.88 (3) Å³	0.20 × 0.15 × 0.06 mm
Z = 4

Data collection top

Bruker X8 Proteum diffractometer	2181 independent reflections
Radiation source: fine-focus rotating anode	2121 reflections with I > 2σ(I)
Graded multilayer optics monochromator	R_int = 0.035
Detector resolution: 5.6 pixels mm^-1	θ_max = 68.0°, θ_min = 5.3°
ϕ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS in APEX2; Bruker, 2006)	k = −12→11
T_min = 0.780, T_max = 0.943	l = −16→16
17255 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.088	w = 1/[σ²(F_o²) + (0.0431P)² + 0.777P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2181 reflections	Δρ_max = 0.26 e Å⁻³
191 parameters	Δρ_min = −0.27 e Å⁻³
3 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0029 (7)

Crystal data top

C₁₂H₁₂N₄O₃·H₂O	V = 1208.88 (3) Å³
M_r = 278.27	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 8.3514 (1) Å	µ = 0.99 mm⁻¹
b = 10.7166 (2) Å	T = 90 K
c = 13.9679 (2) Å	0.20 × 0.15 × 0.06 mm
β = 104.755 (1)°

Data collection top

Bruker X8 Proteum diffractometer	2181 independent reflections
Absorption correction: multi-scan (SADABS in APEX2; Bruker, 2006)	2121 reflections with I > 2σ(I)
T_min = 0.780, T_max = 0.943	R_int = 0.035
17255 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	3 restraints
wR(F²) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.26 e Å⁻³
2181 reflections	Δρ_min = −0.27 e Å⁻³
191 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 > 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

	x	y	z	U_iso*/U_eq
O1	−0.09392 (12)	0.10429 (9)	0.10391 (7)	0.0184 (2)
N1	−0.15262 (14)	0.29911 (10)	0.15528 (8)	0.0158 (3)
H1	−0.2381	0.3179	0.1060	0.019*
C1	−0.06677 (16)	0.19095 (12)	0.16253 (9)	0.0146 (3)
C2	−0.08770 (16)	0.37782 (12)	0.23678 (9)	0.0150 (3)
C3	−0.14037 (16)	0.49625 (13)	0.25289 (10)	0.0183 (3)
H3	−0.2307	0.5349	0.2072	0.022*
C4	−0.05487 (17)	0.55663 (13)	0.33926 (10)	0.0192 (3)
H4	−0.0875	0.6383	0.3527	0.023*
C5	0.07679 (16)	0.49981 (13)	0.40589 (10)	0.0179 (3)
H5	0.1332	0.5433	0.4640	0.021*
C6	0.12728 (16)	0.37988 (12)	0.38869 (9)	0.0161 (3)
H6	0.2163	0.3405	0.4348	0.019*
C7	0.04456 (16)	0.31943 (12)	0.30268 (9)	0.0143 (3)
O8	0.03982 (11)	0.09668 (8)	0.32447 (6)	0.0154 (2)
H8	0.0481	0.0270	0.2986	0.023*
C8	0.07032 (16)	0.19298 (12)	0.26163 (9)	0.0142 (3)
C9	0.24325 (16)	0.17641 (12)	0.24175 (9)	0.0134 (3)
H9	0.2513	0.0945	0.2090	0.016*
C10	0.41472 (17)	0.10072 (12)	0.41347 (9)	0.0171 (3)
H10A	0.5352	0.0920	0.4366	0.026*
H10B	0.3655	0.0195	0.3909	0.026*
H10C	0.3705	0.1309	0.4678	0.026*
N10	0.37459 (13)	0.18921 (10)	0.33208 (8)	0.0138 (3)
C11	0.45660 (16)	0.29528 (12)	0.32705 (9)	0.0148 (3)
N11	0.57702 (14)	0.33716 (11)	0.40073 (8)	0.0195 (3)
H11A	0.6067	0.2948	0.4564	0.023*
H11B	0.6276	0.4075	0.3942	0.023*
N12	0.40787 (14)	0.35577 (10)	0.23870 (8)	0.0156 (3)
O13	0.21974 (12)	0.30271 (8)	0.09262 (7)	0.0174 (2)
C13	0.28724 (16)	0.28445 (12)	0.18112 (9)	0.0140 (3)
O1W	0.03730 (13)	0.14500 (11)	0.52700 (8)	0.0256 (3)
H1W	0.023 (2)	0.1260 (19)	0.4666 (13)	0.038*
H2W	−0.058 (2)	0.1453 (19)	0.5402 (14)	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0209 (5)	0.0161 (5)	0.0156 (5)	−0.0002 (4)	−0.0002 (4)	−0.0028 (4)
N1	0.0151 (5)	0.0148 (6)	0.0149 (5)	0.0014 (4)	−0.0010 (4)	0.0007 (4)
C1	0.0150 (6)	0.0141 (6)	0.0140 (6)	−0.0015 (5)	0.0025 (5)	0.0010 (5)
C2	0.0149 (6)	0.0147 (6)	0.0155 (6)	−0.0017 (5)	0.0043 (5)	0.0001 (5)
C3	0.0161 (6)	0.0153 (7)	0.0238 (7)	0.0021 (5)	0.0058 (5)	0.0026 (5)
C4	0.0205 (7)	0.0123 (6)	0.0278 (7)	−0.0005 (5)	0.0117 (6)	−0.0025 (5)
C5	0.0201 (7)	0.0169 (7)	0.0182 (7)	−0.0046 (5)	0.0079 (5)	−0.0044 (5)
C6	0.0170 (6)	0.0160 (7)	0.0153 (6)	−0.0013 (5)	0.0040 (5)	−0.0002 (5)
C7	0.0157 (6)	0.0120 (6)	0.0151 (6)	−0.0003 (5)	0.0038 (5)	0.0003 (5)
O8	0.0198 (5)	0.0106 (5)	0.0151 (5)	−0.0008 (4)	0.0032 (4)	0.0000 (3)
C8	0.0164 (7)	0.0116 (6)	0.0128 (6)	0.0004 (5)	0.0007 (5)	0.0007 (5)
C9	0.0155 (6)	0.0111 (6)	0.0115 (6)	0.0006 (5)	−0.0004 (5)	−0.0004 (5)
C10	0.0201 (7)	0.0139 (6)	0.0146 (6)	0.0003 (5)	−0.0006 (5)	0.0034 (5)
N10	0.0153 (5)	0.0113 (5)	0.0124 (5)	−0.0002 (4)	−0.0009 (4)	0.0013 (4)
C11	0.0156 (6)	0.0132 (6)	0.0147 (6)	0.0008 (5)	0.0026 (5)	−0.0001 (5)
N11	0.0228 (6)	0.0159 (6)	0.0156 (6)	−0.0059 (5)	−0.0029 (5)	0.0029 (4)
N12	0.0186 (6)	0.0129 (5)	0.0134 (5)	−0.0008 (4)	0.0006 (4)	0.0011 (4)
O13	0.0215 (5)	0.0154 (5)	0.0128 (5)	0.0004 (4)	−0.0003 (4)	0.0010 (3)
C13	0.0157 (6)	0.0116 (6)	0.0140 (6)	0.0030 (5)	0.0024 (5)	0.0000 (5)
O1W	0.0214 (5)	0.0353 (6)	0.0184 (5)	−0.0051 (4)	0.0019 (4)	−0.0057 (4)

Geometric parameters (Å, º) top

O1—C1	1.2206 (16)	C8—C9	1.5488 (18)
N1—C1	1.3531 (17)	C9—N10	1.4522 (16)
N1—C2	1.4096 (17)	C9—C13	1.5334 (17)
N1—H1	0.8800	C9—H9	1.0000
C1—C8	1.5557 (17)	C10—N10	1.4525 (16)
C2—C3	1.3803 (19)	C10—H10A	0.9800
C2—C7	1.3932 (18)	C10—H10B	0.9800
C3—C4	1.395 (2)	C10—H10C	0.9800
C3—H3	0.9500	N10—C11	1.3382 (17)
C4—C5	1.387 (2)	C11—N11	1.3209 (17)
C4—H4	0.9500	C11—N12	1.3612 (17)
C5—C6	1.3925 (19)	N11—H11A	0.8800
C5—H5	0.9500	N11—H11B	0.8800
C6—C7	1.3847 (18)	N12—C13	1.3540 (17)
C6—H6	0.9500	O13—C13	1.2366 (16)
C7—C8	1.5080 (17)	O1W—H1W	0.847 (18)
O8—C8	1.4192 (15)	O1W—H2W	0.861 (18)
O8—H8	0.8400

C1—N1—C2	111.39 (11)	C7—C8—C1	101.94 (10)
C1—N1—H1	124.3	C9—C8—C1	110.33 (10)
C2—N1—H1	124.3	N10—C9—C13	100.04 (10)
O1—C1—N1	126.67 (12)	N10—C9—C8	111.46 (10)
O1—C1—C8	125.20 (11)	C13—C9—C8	112.21 (10)
N1—C1—C8	108.08 (10)	N10—C9—H9	110.9
C3—C2—C7	122.50 (12)	C13—C9—H9	110.9
C3—C2—N1	127.51 (12)	C8—C9—H9	110.9
C7—C2—N1	109.99 (11)	N10—C10—H10A	109.5
C2—C3—C4	116.96 (12)	N10—C10—H10B	109.5
C2—C3—H3	121.5	H10A—C10—H10B	109.5
C4—C3—H3	121.5	N10—C10—H10C	109.5
C5—C4—C3	121.36 (12)	H10A—C10—H10C	109.5
C5—C4—H4	119.3	H10B—C10—H10C	109.5
C3—C4—H4	119.3	C11—N10—C9	108.54 (10)
C4—C5—C6	120.82 (12)	C11—N10—C10	125.20 (11)
C4—C5—H5	119.6	C9—N10—C10	126.23 (10)
C6—C5—H5	119.6	N11—C11—N10	123.09 (12)
C7—C6—C5	118.39 (12)	N11—C11—N12	122.48 (12)
C7—C6—H6	120.8	N10—C11—N12	114.41 (11)
C5—C6—H6	120.8	C11—N11—H11A	120.0
C6—C7—C2	119.96 (12)	C11—N11—H11B	120.0
C6—C7—C8	131.47 (12)	H11A—N11—H11B	120.0
C2—C7—C8	108.56 (11)	C13—N12—C11	105.97 (11)
C8—O8—H8	109.5	O13—C13—N12	125.82 (12)
O8—C8—C7	110.67 (10)	O13—C13—C9	124.01 (11)
O8—C8—C9	110.48 (10)	N12—C13—C9	110.17 (10)
C7—C8—C9	113.64 (10)	H1W—O1W—H2W	108.3 (17)
O8—C8—C1	109.44 (10)

C2—N1—C1—O1	179.49 (12)	O1—C1—C8—C9	59.80 (16)
C2—N1—C1—C8	1.73 (14)	N1—C1—C8—C9	−122.39 (11)
C1—N1—C2—C3	177.98 (13)	O8—C8—C9—N10	−64.03 (13)
C1—N1—C2—C7	−1.42 (15)	C7—C8—C9—N10	61.06 (14)
C7—C2—C3—C4	−0.05 (19)	C1—C8—C9—N10	174.83 (10)
N1—C2—C3—C4	−179.38 (12)	O8—C8—C9—C13	−175.30 (10)
C2—C3—C4—C5	−0.16 (19)	C7—C8—C9—C13	−50.22 (14)
C3—C4—C5—C6	−0.3 (2)	C1—C8—C9—C13	63.55 (13)
C4—C5—C6—C7	1.00 (19)	C13—C9—N10—C11	8.33 (13)
C5—C6—C7—C2	−1.19 (19)	C8—C9—N10—C11	−110.49 (12)
C5—C6—C7—C8	178.47 (13)	C13—C9—N10—C10	−169.97 (11)
C3—C2—C7—C6	0.7 (2)	C8—C9—N10—C10	71.21 (15)
N1—C2—C7—C6	−179.82 (11)	C9—N10—C11—N11	175.73 (12)
C3—C2—C7—C8	−179.00 (12)	C10—N10—C11—N11	−5.9 (2)
N1—C2—C7—C8	0.44 (14)	C9—N10—C11—N12	−5.46 (15)
C6—C7—C8—O8	64.51 (18)	C10—N10—C11—N12	172.86 (11)
C2—C7—C8—O8	−115.79 (12)	N11—C11—N12—C13	178.05 (12)
C6—C7—C8—C9	−60.47 (18)	N10—C11—N12—C13	−0.77 (15)
C2—C7—C8—C9	119.23 (12)	C11—N12—C13—O13	−174.16 (12)
C6—C7—C8—C1	−179.17 (13)	C11—N12—C13—C9	6.41 (14)
C2—C7—C8—C1	0.53 (13)	N10—C9—C13—O13	171.44 (12)
O1—C1—C8—O8	−61.96 (16)	C8—C9—C13—O13	−70.29 (16)
N1—C1—C8—O8	115.85 (11)	N10—C9—C13—N12	−9.12 (13)
O1—C1—C8—C7	−179.17 (12)	C8—C9—C13—N12	109.15 (12)
N1—C1—C8—C7	−1.36 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1Wⁱ	0.88	1.96	2.8128 (15)	163
O8—H8···N12ⁱⁱ	0.84	1.97	2.7984 (14)	170
N11—H11A···O13ⁱⁱⁱ	0.88	2.17	3.0371 (15)	171
N11—H11B···O1^iv	0.88	2.13	2.8678 (15)	141
O1W—H1W···O8	0.85 (2)	2.05 (2)	2.8812 (14)	167 (2)
O1W—H2W···O13^v	0.86 (2)	2.23 (2)	3.0702 (14)	164 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₂H₁₂N₄O₃·H₂O
M_r	278.27
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	90
a, b, c (Å)	8.3514 (1), 10.7166 (2), 13.9679 (2)
β (°)	104.755 (1)
V (Å³)	1208.88 (3)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.99
Crystal size (mm)	0.20 × 0.15 × 0.06

Data collection
Diffractometer	Bruker X8 Proteum diffractometer
Absorption correction	Multi-scan (SADABS in APEX2; Bruker, 2006)
T_min, T_max	0.780, 0.943
No. of measured, independent and observed [I > 2σ(I)] reflections	17255, 2181, 2121
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.088, 1.04
No. of reflections	2181
No. of parameters	191
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.27

Computer programs: APEX2 (Bruker, 2006), SHELXS97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and local procedures.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1Wⁱ	0.88	1.96	2.8128 (15)	163.1
O8—H8···N12ⁱⁱ	0.84	1.97	2.7984 (14)	169.8
N11—H11A···O13ⁱⁱⁱ	0.88	2.17	3.0371 (15)	170.8
N11—H11B···O1^iv	0.88	2.13	2.8678 (15)	141.1
O1W—H1W···O8	0.847 (18)	2.049 (18)	2.8812 (14)	167.4 (19)
O1W—H2W···O13^v	0.861 (18)	2.233 (18)	3.0702 (14)	164.1 (19)

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

Acknowledgements

This investigation was supported by the NIH/National Cancer Institute [grant No. PO1CA104457 (to PAC)] and by the NSF [MRI grant No. CHE 0319176 (to SP)].

References

Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc, Madison, Wisconsin, USA. Google Scholar
Frolova, N. A., Kravtsov, V. K., Biyushkin, V. N., Chumakov, Yu. M., Bel'kova, O. N. & Malinovskii, T. I. (1988). J. Struct. Chem. 29, 491–493. CrossRef Web of Science Google Scholar
Sekhar, K. R., Crooks, P. A., Sonar, V. N., Friedman, D. B., Chan, J. Y., Meredith, M. J., Stames, J. H., Kelton, K. R., Summar, S. R., Sasi, S. & Freeman, M. L. (2003). Cancer Res. 63, 5636–5645. Web of Science PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sonar, V. N., Reddy, Y. T., Sekhar, K. R., Sowmya, S., Freeman, M. L. & Crooks, P. A. (2007). Bioorg. Med. Chem. Lett. 17, 6821–6824. Web of Science CrossRef PubMed CAS Google Scholar
Usman, A., Razak, I. A., Fun, H.-K., Chantrapromma, S., Zhao, B.-G. & Xu, J.-H. (2002). Acta Cryst. C58, o24–o25. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

3-(2-Amino-1-methyl-4-oxo-4,5-di­hydro-1H-imidazol-5-yl)-3-hy­droxy­indolin-2-one monohydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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organic compounds

3-(2-Amino-1-methyl-4-oxo-4,5-dihydro-1H-imidazol-5-yl)-3-hydroxyindolin-2-one monohydrate