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

Elmuradov, B.Z.; Turgunov, K.; Tashkhodjaev, B.; Shakhidoyatov, K.M.

doi:10.1107/S1600536810014303

organic compounds

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ISSN: 2056-9890

Volume 66| Part 5| May 2010| Page o1238

https://doi.org/10.1107/S1600536810014303

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

Burkhon Zh Elmuradov,^a ^* Kambarali Turgunov,^a Bakhodir Tashkhodjaev ^a and Khusniddin M. Shakhidoyatov ^a

^aS.Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of Uzbekistan, Mirzo Ulugbek Str. 77, Tashkent 100170, Uzbekistan
^*Correspondence e-mail: burkhon@rambler.ru

(Received 12 April 2010; accepted 19 April 2010; online 30 April 2010)

The title compound, C₁₅H₁₆N₂O₂·H₂O, was synthesized via the alkylation of 3-hydroxymethylidene-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one with n-propyl iodide in the presence of sodium hydroxide. The organic molecule and the water molecule both lie on a crystallographic mirror plane. In the crystal structure, intermolecular 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_r = 274.31
Monoclinic, P 2₁ /m
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[F² > 2σ(F²)] = 0.064
wR(F²) = 0.144
S = 1.15
1479 reflections
128 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.19 e Å⁻³

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) x+1, y, z.

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.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810014303/lh5028Isup2.hkl

checkCIF report

Comment top

Tricyclic quinazoline alkaloids are a large group of heterocyclic compounds (Späth & Platzer, 1935; Shakhidoyatov et al., 1976; Oripov et al., 1979; Elmuradov & Shakhidoyatov, 2006; Jahng et al., 2008). These compounds and their derivatives possess different pharmacological activities (Amin & Mehta1959; Chatterjee & Ganguly, 1968; Yakhontov et al., 1977; Yunusov et al., 1978; Johne, 1981; Shakhidoyatov, 1988).

Alkylation of 3- hydroxymethylidene-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one with C1—C3 alkyl halides leads to the formation of new C-alkyl (Elmuradov & Shakhidoyatov, 2004) or O-alkyl derivatives (Elmuradov et al., 2006). Using the typical synthesis for O-alkyl derivatives the reaction of 3- hydroxymethylidene-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one with n-propyl iodide was carried out by boiling of the initial reagents (1:2 ratio) over 7 hours in ethanol in the presence of sodium hydroxide (Elmuradov et al., 2006) (Figure 1). The compound (3-hydroxymethylidene-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin- 9-one) is obtained by formylation of 2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one (alkaloid Deoxyvasicinone, isolated from Peganum Harmala) (Chatterjee & Ganguly, 1968) with Vilsmeier-Haack reagent.

The asymmetric unit contains half molecule of 3-propoxymethylidene-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9- one and a half water molecule (Figure 2). Both molecules of the asymetric unit lay on the crystallographic mirror plane. The water molecule links the N and Oⁱ atoms of title compound molecule by O—H···N and O—H···Oⁱ hydrogen bonds, which form a H-bond chain along [100] (Figure 3). The bond distances (Allen et al., 1987) and angles in molecule are in normal ranges.

Related literature top

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 top

Sodium hydroxide (0.08 g, 2 mmol) was dissolved in ethanol (10 ml), and 3-hydroxymethylidene-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one (0.214 g, 1 mmol) and propyl iodide (0.34 g, 0.18 ml, d=1.747 g/ml, 2 mmol) were added. The mixture was heated to reflux on a water bath for 7 hours. The solvent was distilled off and the residue was re-crystallized from hexane. The title compound was obtained in 70 % yield (0.18 g). Colorless crystals suitable for X-ray analysis were obtained from hexane by slow evaporation.

Structure description top

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).

Computing details top

Data collection: STADI4 (Stoe & Cie, 1997); cell refinement: STADI4 (Stoe & Cie, 1997); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The reaction scheme.
	Fig. 2. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms.
	Fig. 3. Part of the crystal structure of (I), showing the formation of hydrogen-bonded (dashed lines) chains along [100].

(E)-3-Propoxymethylidene-2,3-dihydro-1H- pyrrolo[2,1-b]quinazolin-9-one monohydrate top

Crystal data top

C₁₅H₁₆N₂O₂·H₂O	F(000) = 292
M_r = 274.31	D_x = 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

Data collection top

Stoe Stadi-4 four-circle diffractometer	R_int = 0.000
Radiation source: fine-focus sealed tube	θ_max = 26.0°, θ_min = 1.9°
Graphite monochromator	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 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)] = 0.064	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.144	w = 1/[σ²(F_o²) + (0.034P)² + 0.5511P] where P = (F_o² + 2F_c²)/3
S = 1.15	(Δ/σ)_max < 0.001
1479 reflections	Δρ_max = 0.21 e Å⁻³
128 parameters	Δρ_min = −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)

Crystal data top

C₁₅H₁₆N₂O₂·H₂O	V = 689.6 (2) Å³
M_r = 274.31	Z = 2
Monoclinic, P2₁/m	Mo Kα radiation
a = 9.247 (2) Å	µ = 0.09 mm⁻¹
b = 6.876 (1) Å	T = 293 K
c = 10.950 (2) Å	0.75 × 0.53 × 0.20 mm
β = 97.90 (3)°

Data collection top

Stoe Stadi-4 four-circle diffractometer	R_int = 0.000
1483 measured reflections	3 standard reflections every 60 min
1479 independent reflections	intensity decay: 2%
1000 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.064	0 restraints
wR(F²) = 0.144	H atoms treated by a mixture of independent and constrained refinement
S = 1.15	Δρ_max = 0.21 e Å⁻³
1479 reflections	Δρ_min = −0.19 e Å⁻³
128 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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)*

Atomic displacement parameters (Å²) top

	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

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₆N₂O₂·H₂O
M_r	274.31
Crystal system, space group	Monoclinic, P2₁/m
Temperature (K)	293
a, b, c (Å)	9.247 (2), 6.876 (1), 10.950 (2)
β (°)	97.90 (3)
V (Å³)	689.6 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.75 × 0.53 × 0.20

Data collection
Diffractometer	Stoe Stadi-4 four-circle
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	1483, 1479, 1000
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.144, 1.15
No. of reflections	1479
No. of parameters	128
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.19

Computer programs: STADI4 (Stoe & Cie, 1997), X-RED (Stoe & Cie, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Bruker, 1998).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1···N1	0.85 (7)	2.135 (77)	2.968 (5)	165 (7)
O1w—H2···O2ⁱ	0.90 (7)	1.948 (71)	2.855 (5)	176 (6)

Symmetry code: (i) x+1, y, z.

Acknowledgements

We thank the Academy of Sciences of the Republic of Uzbekistan for supporting this study (grant FA–F3–T047).

References

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Volume 66| Part 5| May 2010| Page o1238

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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