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

Two chiral centres exist in the title compound, C(12)H(12)N(4)O(3)·H(2)O. Mol-ecules are linked into chains by series of inter-molecular N-H⋯O and O-H⋯N hydrogen bonds, which causes supra-molecular 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 enantio-mers (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 = 278.27

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.088

S = 1.04

2181 reflections

191 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.27 e Å−3

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C12H12N4O3·H2O	F(000) = 584
Mr = 278.27	Dx = 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

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

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(Fo2) + (0.0431P)2 + 0.777P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2181 reflections	Δρmax = 0.26 e Å−3
191 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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···O1iv	0.88	2.13	2.8678 (15)	141
O1W—H1W···O8	0.85 (2)	2.05 (2)	2.8812 (14)	167 (2)
O1W—H2W···O13v	0.86 (2)	2.23 (2)	3.0702 (14)	164 (2)

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⋯O1iv	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⋯O13v	0.861 (18)	2.233 (18)	3.0702 (14)	164.1 (19)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .