(E)-3-Propoxymethyl-idene-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one monohydrate.

The title compound, C(15)H(16)N(2)O(2)·H(2)O, was synthesized via the alkyl-ation of 3-hydroxy-methyl-idene-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one with n-propyl iodide in the presence of sodium hydroxide. The organic mol-ecule and the water mol-ecule both lie on a crystallographic mirror plane. In the crystal structure, inter-molecular O-H⋯O and O-H⋯N hydrogen bonds link the components into extended chains along [100].

Related literature

For the synthesis of the title compound and its derivatives, see: Späth & Platzer, (1935 ▶); Shakhidoyatov et al. (1976 ▶); Oripov et al. (1979 ▶); Elmuradov et al. (2006 ▶); Elmuradov & Shakhidoyatov (2004 ▶); Jahng et al. (2008 ▶). For the physiological activity of the title compound and its derivatives, see: Amin & Mehta (1959 ▶); Chatterjee & Ganguly (1968 ▶); Yakhontov et al. (1977 ▶); Yunusov et al. (1978 ▶); Johne (1981 ▶); Shakhidoyatov (1988 ▶). For standard bond distances, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H16N2O2·H2O

M = 274.31

Monoclinic,

a = 9.247 (2) Å

b = 6.876 (1) Å

c = 10.950 (2) Å

β = 97.90 (3)°

V = 689.6 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.75 × 0.53 × 0.20 mm

Data collection

Stoe Stadi-4 four-circle diffractometer

1483 measured reflections

1479 independent reflections

1000 reflections with I > 2σ(I)

3 standard reflections every 60 min intensity decay: 2%

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.144

S = 1.15

1479 reflections

128 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.19 e Å−3

Data collection: STADI4 (Stoe & Cie, 1997 ▶); cell refinement: STADI4; data reduction: X-RED (Stoe & Cie, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Bruker, 1998 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810014303/lh5028sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810014303/lh5028Isup2.hkl

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

C15H16N2O2·H2O	F(000) = 292
Mr = 274.31	Dx = 1.321 Mg m−3
Monoclinic, P21/m	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yb	Cell parameters from 15 reflections
a = 9.247 (2) Å	θ = 5–10°
b = 6.876 (1) Å	µ = 0.09 mm−1
c = 10.950 (2) Å	T = 293 K
β = 97.90 (3)°	Prism, colourless
V = 689.6 (2) Å3	0.75 × 0.53 × 0.20 mm
Z = 2

Stoe Stadi-4 four-circle diffractometer	Rint = 0.0000
Radiation source: fine-focus sealed tube	θmax = 26.0°, θmin = 1.9°
graphite	h = −11→11
Scan width (ω) = 1.56–1.68, scan ratio 2θ:ω = 1.00 I(Net) and σ(I) calculated according to Blessing (1987)[Blessing, R. H. (1987). Cryst. Rev.1, 3–58]	k = 0→8
1483 measured reflections	l = 0→13
1479 independent reflections	3 standard reflections every 60 min
1000 reflections with I > 2σ(I)	intensity decay: 2%

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)] = 0.064	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.144	w = 1/[σ2(Fo2) + (0.034P)2 + 0.5511P] where P = (Fo2 + 2Fc2)/3
S = 1.15	(Δ/σ)max < 0.001
1479 reflections	Δρmax = 0.21 e Å−3
128 parameters	Δρmin = −0.19 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.009 (2)

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 > 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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.7289 (3)	0.2500	0.2635 (2)	0.0522 (8)
O2	0.1375 (3)	0.2500	0.5696 (3)	0.0682 (10)
N1	0.5853 (3)	0.2500	0.6240 (3)	0.0390 (8)
C2	0.5055 (4)	0.2500	0.5163 (3)	0.0349 (9)
N3	0.3551 (3)	0.2500	0.4988 (3)	0.0370 (8)
C4	0.2711 (4)	0.2500	0.5924 (3)	0.0430 (10)
C4A	0.3567 (4)	0.2500	0.7153 (3)	0.0384 (9)
C5	0.2880 (4)	0.2500	0.8207 (4)	0.0493 (11)
H5A	0.1865	0.2500	0.8133	0.059*
C6	0.3684 (4)	0.2500	0.9343 (4)	0.0546 (12)
H6A	0.3215	0.2500	1.0043	0.066*
C7	0.5192 (5)	0.2500	0.9468 (4)	0.0531 (11)
H7A	0.5731	0.2500	1.0251	0.064*
C8	0.5901 (4)	0.2500	0.8445 (3)	0.0448 (10)
H8A	0.6916	0.2500	0.8539	0.054*
C8A	0.5102 (4)	0.2500	0.7258 (3)	0.0355 (9)
C9	0.5544 (4)	0.2500	0.3964 (3)	0.0384 (9)
C10	0.4244 (4)	0.2500	0.2975 (3)	0.0452 (10)
H10A	0.4243	0.1352	0.2460	0.054*	0.50
H10B	0.4243	0.3648	0.2460	0.054*	0.50
C11	0.2918 (4)	0.2500	0.3684 (3)	0.0472 (10)
H11A	0.2322	0.3648	0.3486	0.057*	0.50
H11B	0.2322	0.1352	0.3486	0.057*	0.50
C12	0.6934 (4)	0.2500	0.3777 (3)	0.0447 (10)
H12A	0.7667	0.2500	0.4449	0.054*
C13	0.8823 (4)	0.2500	0.2525 (4)	0.0586 (13)
H13A	0.9291	0.1354	0.2916	0.070*	0.50
H13B	0.9291	0.3646	0.2916	0.070*	0.50
C14	0.8937 (5)	0.2500	0.1161 (4)	0.0673 (14)
H14A	0.8438	0.1361	0.0788	0.081*	0.50
H14B	0.8438	0.3639	0.0788	0.081*	0.50
C15	1.0456 (5)	0.2500	0.0877 (5)	0.096 (2)
H15A	1.0448	0.2500	−0.0001	0.144*
H15B	1.0953	0.1360	0.1224	0.144*	0.50
H15C	1.0953	0.3640	0.1224	0.144*	0.50
O1W	0.9030 (4)	0.2500	0.7141 (4)	0.1047 (17)
H2	0.975 (8)	0.2500	0.665 (6)	0.15 (3)*
H1	0.816 (8)	0.2500	0.676 (7)	0.17 (3)*

	U11	U22	U33	U12	U13	U23
O1	0.0461 (16)	0.078 (2)	0.0357 (15)	0.000	0.0161 (12)	0.000
O2	0.0307 (15)	0.126 (3)	0.0479 (17)	0.000	0.0058 (12)	0.000
N1	0.0308 (16)	0.050 (2)	0.0367 (17)	0.000	0.0074 (13)	0.000
C2	0.0345 (18)	0.036 (2)	0.035 (2)	0.000	0.0094 (15)	0.000
N3	0.0347 (16)	0.045 (2)	0.0310 (16)	0.000	0.0030 (13)	0.000
C4	0.039 (2)	0.055 (3)	0.037 (2)	0.000	0.0115 (16)	0.000
C4A	0.0354 (19)	0.045 (2)	0.0363 (19)	0.000	0.0099 (15)	0.000
C5	0.037 (2)	0.070 (3)	0.043 (2)	0.000	0.0093 (17)	0.000
C6	0.049 (2)	0.082 (3)	0.037 (2)	0.000	0.0172 (18)	0.000
C7	0.055 (3)	0.070 (3)	0.034 (2)	0.000	0.0061 (18)	0.000
C8	0.038 (2)	0.061 (3)	0.036 (2)	0.000	0.0033 (16)	0.000
C8A	0.0328 (19)	0.039 (2)	0.036 (2)	0.000	0.0093 (15)	0.000
C9	0.043 (2)	0.041 (2)	0.0321 (19)	0.000	0.0089 (16)	0.000
C10	0.055 (2)	0.048 (3)	0.032 (2)	0.000	0.0055 (17)	0.000
C11	0.043 (2)	0.065 (3)	0.033 (2)	0.000	0.0015 (16)	0.000
C12	0.048 (2)	0.055 (3)	0.031 (2)	0.000	0.0086 (17)	0.000
C13	0.044 (2)	0.087 (4)	0.049 (2)	0.000	0.0206 (19)	0.000
C14	0.054 (3)	0.104 (4)	0.049 (3)	0.000	0.022 (2)	0.000
C15	0.063 (3)	0.164 (7)	0.063 (3)	0.000	0.020 (3)	0.000
O1W	0.046 (2)	0.204 (5)	0.065 (2)	0.000	0.0116 (19)	0.000

O1—C12	1.336 (4)	C9—C12	1.329 (5)
O1—C13	1.439 (4)	C9—C10	1.502 (5)
O2—C4	1.226 (4)	C10—C11	1.539 (5)
N1—C2	1.302 (4)	C10—H10A	0.9700
N1—C8A	1.391 (4)	C10—H10B	0.9700
C2—N3	1.377 (4)	C11—H11A	0.9700
C2—C9	1.447 (5)	C11—H11B	0.9700
N3—C4	1.369 (4)	C12—H12A	0.9300
N3—C11	1.467 (4)	C13—C14	1.512 (5)
C4—C4A	1.464 (5)	C13—H13A	0.9700
C4A—C5	1.392 (5)	C13—H13B	0.9700
C4A—C8A	1.408 (5)	C14—C15	1.479 (6)
C5—C6	1.359 (5)	C14—H14A	0.9700
C5—H5A	0.9300	C14—H14B	0.9700
C6—C7	1.383 (5)	C15—H15A	0.9600
C6—H6A	0.9300	C15—H15B	0.9600
C7—C8	1.374 (5)	C15—H15C	0.9600
C7—H7A	0.9300	O1W—H2	0.91 (7)
C8—C8A	1.404 (5)	O1W—H1	0.85 (8)
C8—H8A	0.9300
C12—O1—C13	116.8 (3)	C9—C10—H10A	110.8
C2—N1—C8A	116.3 (3)	C11—C10—H10A	110.8
N1—C2—N3	124.2 (3)	C9—C10—H10B	110.8
N1—C2—C9	127.8 (3)	C11—C10—H10B	110.8
N3—C2—C9	108.0 (3)	H10A—C10—H10B	108.9
C4—N3—C2	124.2 (3)	N3—C11—C10	104.6 (3)
C4—N3—C11	122.5 (3)	N3—C11—H11A	110.8
C2—N3—C11	113.3 (3)	C10—C11—H11A	110.8
O2—C4—N3	120.4 (4)	N3—C11—H11B	110.8
O2—C4—C4A	126.2 (3)	C10—C11—H11B	110.8
N3—C4—C4A	113.4 (3)	H11A—C11—H11B	108.9
C5—C4A—C8A	120.2 (3)	C9—C12—O1	120.8 (3)
C5—C4A—C4	120.7 (3)	C9—C12—H12A	119.6
C8A—C4A—C4	119.1 (3)	O1—C12—H12A	119.6
C6—C5—C4A	120.3 (4)	O1—C13—C14	106.6 (3)
C6—C5—H5A	119.9	O1—C13—H13A	110.4
C4A—C5—H5A	119.9	C14—C13—H13A	110.4
C5—C6—C7	120.6 (4)	O1—C13—H13B	110.4
C5—C6—H6A	119.7	C14—C13—H13B	110.4
C7—C6—H6A	119.7	H13A—C13—H13B	108.6
C8—C7—C6	120.5 (4)	C15—C14—C13	113.9 (4)
C8—C7—H7A	119.8	C15—C14—H14A	108.8
C6—C7—H7A	119.8	C13—C14—H14A	108.8
C7—C8—C8A	120.4 (4)	C15—C14—H14B	108.8
C7—C8—H8A	119.8	C13—C14—H14B	108.8
C8A—C8—H8A	119.8	H14A—C14—H14B	107.7
N1—C8A—C8	119.0 (3)	C14—C15—H15A	109.5
N1—C8A—C4A	122.9 (3)	C14—C15—H15B	109.5
C8—C8A—C4A	118.2 (3)	H15A—C15—H15B	109.5
C12—C9—C2	124.7 (3)	C14—C15—H15C	109.5
C12—C9—C10	125.7 (3)	H15A—C15—H15C	109.5
C2—C9—C10	109.6 (3)	H15B—C15—H15C	109.5
C9—C10—C11	104.5 (3)	H2—O1W—H1	115 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1···N1	0.85 (7)	2.13 (8)	2.968 (5)	165 (7)
O1w—H2···O2i	0.90 (7)	1.95 (7)	2.855 (5)	176 (6)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1w—H1⋯N1	0.85 (7)	2.14 (8)	2.968 (5)	165 (7)
O1w—H2⋯O2i	0.90 (7)	1.95 (7)	2.855 (5)	176 (6)

Symmetry code: (i) .