(4-Nitrophenyl)(1,2,3,9-tetrahydro­pyrrolo[2,1-b]quinazolin-3-yl)methanol monohydrate

Elmuradov, B.Z.; Makhmadiyarova, C.E.; Turgunov, K.K.; Tashkhodjaev, B.; Shakhidoyatov, K.M.

doi:10.1107/S1600536811021775

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1680

doi:10.1107/S1600536811021775

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(4-Nitrophenyl)(1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-3-yl)methanol monohydrate

Burkhon Zh. Elmuradov,^a Charoskhon E. Makhmadiyarova,^a ^* Kambarali K. Turgunov,^a Bakhodir Tashkhodjaev ^a and Khusnutdin 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: ch_mahmadiyorova@rambler.ru

(Received 27 May 2011; accepted 6 June 2011; online 18 June 2011)

In the crystal structure of the title compound, C₁₈H₁₇N₃O₃·H₂O, the molecules are linked by O—H⋯O and O—H⋯N hydrogen bonds, resulting in a chain along the a axis. The crystal structure is stabilized by weak intermolecular C—H⋯π (ring) hydrogen bonds and aromatic π⋯π stacking interactions [centroid–centroid distance = 3.902 (1) Å] between the pyrimidino rings of the quinazoline system. The tricyclic quinazoline fragment is almost planar (rms deviation = 0.0139 Å) with the two methylene C atoms of the pyrrolo ring deviating by 0.148 (2) and −0.081 (3) Å from the plane through the other atoms. The 4-nitrophenyl ring makes a dihedral angle of 12.55 (7)° with the tricyclic ring system.

Related literature

For general background to tricyclic quinazoline alkaloids, see: Shakhidoyatov et al. (1988 ). For the synthesis of 1,2,3,9-tetrahydro-pyrrolo[2,1-b]quinazoline, see: Jahng et al. (2008 ). For the physiological activity of quinazoline derivatives, see: Al-Shamma et al. (1981 ); Yunusov et al. (1978 ).

Experimental

Crystal data

C₁₈H₁₇N₃O₃·H₂O
M_r = 341.36
Triclinic, $[P \overline 1]$
a = 6.2459 (7) Å
b = 11.4629 (11) Å
c = 11.8400 (13) Å
α = 91.932 (8)°
β = 95.589 (9)°
γ = 104.747 (9)°
V = 814.37 (15) Å³
Z = 2
Cu Kα radiation
μ = 0.83 mm⁻¹
T = 295 K
0.50 × 0.35 × 0.15 mm

Data collection

Oxford Diffraction Xcalibur Ruby diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.793, T_max = 1.000
4649 measured reflections
2867 independent reflections
2076 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.124
S = 1.03
2867 reflections
238 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the N1,C2,N3,C4,C4A,C8A and C4A,C5–C8,C8A rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯N1	0.86 (2)	1.89 (3)	2.751 (2)	174 (2)
O1W—H2W⋯O1ⁱ	0.89 (3)	1.97 (3)	2.835 (2)	162 (2)
O1—H1⋯O1Wⁱⁱ	0.95 (4)	1.71 (3)	2.660 (2)	173 (3)
C4—H4B⋯Cg1ⁱⁱⁱ	0.97	2.92	3.634 (2)	131
C11—H11A⋯Cg2ⁱⁱⁱ	0.97	2.94	3.681 (2)	134
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y+1, -z+2; (iii) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811021775/rk2278sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811021775/rk2278Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811021775/rk2278Isup3.cml

checkCIF report

Comment top

Tricyclic quinazoline alkaloids are a large group of heterocyclic compounds (Shakhidoyatov et al., 1988; Jahng et al., 2008). These compounds and their derivatives possess difference pharmacological activities (Al-Shamma et al., 1981; Yunusov et al., 1978). Reaction of 1,2,3,9-tetrahydro-pyrrolo[2,1-b]quinazoline with p-nitrobenzaldehyde in ethanol at present of sodium hydroxide leads to the formation of 3-(p-nitrophenyl)-hydroxymethyl-1,2,3,9-tetrahydro-pyrrolo[2,1- b]quinazoline (Fig. 1). The title molecule has two asymmetric centre. The crystal is a racemate of two optical antipodes. The asymmetric unit contains one molecule of 3-(p-nitrophenyl)-hydroxymethyl-1,2,3,9-tetrahydro-pyrrolo[2,1- b]quinazoline and one water molecule (Fig. 2). In the molecule tryciclic quinazoline fragment almost planar with of slightly twisting of atoms C9 and C10. Deviations of last atoms from plane of rest atoms (rms deviation = 0.0139Å) in the tricycle are 0.148 (2)Å and -0.081 (3)Å, respectively.

Hydroxyl groups of two centrosymmetrical related molecules of title compound and two water molecules form a H-bond regtangles (nearly). In addition the water molecules are hydrogen bonded to the title compound molecules through N1 atom (Table 1). In the result are formed H-bond chains along the a axis of the cell (Fig. 3). The observed structure is stabilized by weak C—H···π (Table 1) and aromatic π···π stacking interactions. A centrosymmetric π···π stacking interactions are observed between pyrimidino (N1/C2/N3/C4/C4A/C8A) rings of centrosymmetrically related molecules (Cg1···Cg1ⁱ separation is 3.902 (1)Å, where symmetry code: (i) 1-x, 1-y, 1-z).

Related literature top

For general background to tricyclic quinazoline alkaloids, see: Shakhidoyatov et al. (1988). For the synthesis of 1,2,3,9-tetrahydro-pyrrolo[2,1-b]quinazoline, see: Jahng et al. (2008). For the physiological activity of quinazoline derivatives, see: Al-Shamma et al. (1981); Yunusov et al. (1978).

Experimental top

Sodium hydroxide (0.1 g, 2.5 mmol) was dissolved in 40 ml ethanol (80%), and 1,2,3,9-tetrahydro-pyrrolo[2,1-b]quinazoline hydrochloride (0.448 g, 2 mmol) and p-nitrobenzaldehyde (0.604 g, 4 mmol) were added (Fig. 1). Reaction mixture was left at 278 (1) K for 5 weeks. Light yellow crystals (m.p. 473–474 K) suitable for X-ray diffraction were isolated in 72% yield (0.44 g).

¹H NMR (400 MHz, C₅H₅N): 8.1 (2H, d, J = 8.8, H-3',5'), 7.9 (1H, s, OH), 7.67 (1H, d, J = 8.6, H-8), 7.67 (2H, d, J = 8.6, H-2',6'), 7.14 (2H, t, J = 8.6, H-6), 6.9 (1H, td, J = 8.6, J = 2.0, H-7), 6.8 (1H, d, J = 7.6, H-5), 5.06 (1H, d, J = 8.4, CH), 4.17 (1H, s, 9-H), 2.94 (1H, q, J = 8.6, H-1a), 2.78 (1H, q, J = 9.4, H-1b), 2.65 (2H, td, J = 8.6, J = 3.3, 3-H), 1.52 (2H, m, 2-H).

Mass (m/z, %): 323 ([M]⁺, 5.6), 305 ([M-H₂O]⁺, 6.3), 201 ([M-C₆H₄NO₂]⁺, 2.8), 171 ([M-(HO)CHC₆H₄NO₂]⁺, 100), 151 (51), 76 (55).

Computing details top

Data collection: CrysAlis PRO, (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO, (Oxford Diffraction, 2009); data reduction: CrysAlis PRO, (Oxford Diffraction, 2009); 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: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The reaction scheme.
	Fig. 2. The molecular structure of title compound with atom labels. The displacement ellipsoidsand are drawn at 50% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 3. Packing diagramm, showing the formation of H-bonded (dashed lines) chains along [1 0 0]. H atoms are omitted for clarity.

(4-Nitrophenyl)(1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-3- yl)methanol monohydrate top

Crystal data top

C₁₈H₁₇N₃O₃·H₂O	Z = 2
M_r = 341.36	F(000) = 360
Triclinic, P1	D_x = 1.392 Mg m⁻³
Hall symbol: -P 1	Melting point = 473(2)–474(2) K
a = 6.2459 (7) Å	Cu Kα radiation, λ = 1.54180 Å
b = 11.4629 (11) Å	Cell parameters from 1912 reflections
c = 11.8400 (13) Å	θ = 3.8–66.8°
α = 91.932 (8)°	µ = 0.83 mm⁻¹
β = 95.589 (9)°	T = 295 K
γ = 104.747 (9)°	Prism, light-yellow
V = 814.37 (15) Å³	0.50 × 0.35 × 0.15 mm

Data collection top

Oxford Diffraction Xcalibur Ruby diffractometer	2867 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2076 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
Detector resolution: 10.2576 pixels mm^-1	θ_max = 66.9°, θ_min = 3.8°
ω–scans	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −13→13
T_min = 0.793, T_max = 1.000	l = −11→14
4649 measured reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0752P)² + 0.0389P] where P = (F_o² + 2F_c²)/3
2867 reflections	(Δ/σ)_max = 0.001
238 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₈H₁₇N₃O₃·H₂O	γ = 104.747 (9)°
M_r = 341.36	V = 814.37 (15) Å³
Triclinic, P1	Z = 2
a = 6.2459 (7) Å	Cu Kα radiation
b = 11.4629 (11) Å	µ = 0.83 mm⁻¹
c = 11.8400 (13) Å	T = 295 K
α = 91.932 (8)°	0.50 × 0.35 × 0.15 mm
β = 95.589 (9)°

Data collection top

Oxford Diffraction Xcalibur Ruby diffractometer	2867 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	2076 reflections with I > 2σ(I)
T_min = 0.793, T_max = 1.000	R_int = 0.022
4649 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.18 e Å⁻³
2867 reflections	Δρ_min = −0.20 e Å⁻³
238 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
O1	0.8540 (2)	0.61715 (12)	0.92847 (12)	0.0555 (4)
O2	0.6598 (3)	1.09493 (15)	1.24380 (17)	0.0991 (6)
O3	0.3240 (3)	0.99048 (18)	1.24831 (17)	0.1005 (6)
N1	0.3825 (2)	0.45278 (13)	0.71834 (12)	0.0471 (4)
C2	0.5561 (3)	0.54174 (16)	0.71298 (14)	0.0427 (4)
N3	0.7234 (2)	0.54380 (13)	0.65065 (13)	0.0487 (4)
C4	0.7416 (3)	0.44111 (18)	0.58074 (16)	0.0537 (5)
H4A	0.8783	0.4197	0.6060	0.064*
H4B	0.7473	0.4624	0.5023	0.064*
C4A	0.5454 (3)	0.33484 (17)	0.58861 (15)	0.0475 (4)
C5	0.5291 (4)	0.22532 (19)	0.53039 (18)	0.0636 (6)
H5A	0.6415	0.2178	0.4868	0.076*
C6	0.3493 (4)	0.1273 (2)	0.5359 (2)	0.0700 (6)
H6A	0.3414	0.0545	0.4964	0.084*
C7	0.1821 (4)	0.13746 (18)	0.59957 (19)	0.0643 (6)
H7A	0.0599	0.0719	0.6028	0.077*
C8	0.1959 (3)	0.24550 (17)	0.65902 (17)	0.0558 (5)
H8A	0.0828	0.2518	0.7027	0.067*
C8A	0.3761 (3)	0.34467 (16)	0.65443 (14)	0.0451 (4)
C9	0.5996 (3)	0.65999 (15)	0.78287 (15)	0.0457 (4)
H9A	0.4710	0.6940	0.7698	0.055*
C10	0.8016 (4)	0.74163 (18)	0.73443 (18)	0.0609 (5)
H10A	0.7562	0.8017	0.6888	0.073*
H10B	0.9129	0.7828	0.7955	0.073*
C11	0.8949 (3)	0.65817 (18)	0.66131 (18)	0.0575 (5)
H11A	0.9194	0.6898	0.5874	0.069*
H11B	1.0345	0.6483	0.6980	0.069*
C12	0.6388 (3)	0.63750 (15)	0.90930 (14)	0.0433 (4)
H12A	0.5295	0.5631	0.9240	0.052*
C13	0.6112 (3)	0.73811 (15)	0.98840 (14)	0.0425 (4)
C14	0.7810 (3)	0.83964 (17)	1.02340 (17)	0.0563 (5)
H14A	0.9196	0.8485	0.9973	0.068*
C15	0.7481 (3)	0.92825 (17)	1.09669 (18)	0.0611 (5)
H15A	0.8630	0.9967	1.1193	0.073*
C16	0.5446 (3)	0.91394 (16)	1.13547 (16)	0.0510 (5)
C17	0.3738 (3)	0.8124 (2)	1.10522 (19)	0.0652 (6)
H17A	0.2373	0.8026	1.1340	0.078*
C18	0.4091 (3)	0.72560 (19)	1.03133 (19)	0.0619 (6)
H18A	0.2942	0.6568	1.0098	0.074*
N19	0.5065 (4)	1.00649 (17)	1.21455 (16)	0.0689 (5)
H1	0.878 (4)	0.600 (3)	1.006 (3)	0.113 (10)*
O1W	0.0490 (2)	0.43285 (14)	0.85779 (12)	0.0573 (4)
H1W	0.151 (4)	0.444 (2)	0.812 (2)	0.081 (8)*
H2W	−0.024 (4)	0.490 (3)	0.864 (2)	0.107 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0543 (8)	0.0736 (9)	0.0481 (8)	0.0331 (7)	0.0083 (6)	0.0005 (7)
O2	0.1175 (15)	0.0596 (10)	0.1127 (15)	0.0132 (10)	0.0153 (11)	−0.0336 (10)
O3	0.0964 (13)	0.1053 (13)	0.1106 (15)	0.0431 (11)	0.0318 (11)	−0.0328 (11)
N1	0.0458 (8)	0.0505 (9)	0.0447 (8)	0.0111 (7)	0.0108 (7)	−0.0062 (7)
C2	0.0426 (9)	0.0493 (10)	0.0379 (9)	0.0156 (8)	0.0039 (7)	0.0014 (7)
N3	0.0474 (8)	0.0537 (9)	0.0458 (9)	0.0118 (7)	0.0136 (7)	−0.0008 (7)
C4	0.0515 (11)	0.0680 (12)	0.0460 (11)	0.0219 (9)	0.0116 (8)	−0.0019 (9)
C4A	0.0520 (10)	0.0563 (11)	0.0376 (9)	0.0212 (9)	0.0036 (8)	−0.0013 (8)
C5	0.0705 (14)	0.0696 (14)	0.0563 (12)	0.0293 (11)	0.0087 (10)	−0.0112 (10)
C6	0.0858 (16)	0.0566 (12)	0.0676 (14)	0.0239 (12)	0.0001 (12)	−0.0163 (11)
C7	0.0711 (14)	0.0504 (11)	0.0652 (13)	0.0071 (10)	0.0025 (11)	−0.0043 (10)
C8	0.0588 (12)	0.0556 (11)	0.0521 (12)	0.0125 (9)	0.0103 (9)	−0.0020 (9)
C8A	0.0498 (10)	0.0481 (10)	0.0381 (9)	0.0147 (8)	0.0038 (8)	0.0000 (7)
C9	0.0472 (10)	0.0466 (9)	0.0443 (10)	0.0153 (8)	0.0032 (8)	−0.0012 (8)
C10	0.0749 (14)	0.0518 (11)	0.0520 (12)	0.0069 (10)	0.0126 (10)	0.0050 (9)
C11	0.0522 (11)	0.0611 (12)	0.0553 (12)	0.0051 (9)	0.0111 (9)	0.0072 (9)
C12	0.0404 (9)	0.0465 (9)	0.0447 (10)	0.0130 (8)	0.0097 (7)	−0.0007 (8)
C13	0.0394 (9)	0.0471 (9)	0.0412 (9)	0.0121 (8)	0.0042 (7)	0.0001 (7)
C14	0.0465 (10)	0.0555 (11)	0.0630 (13)	0.0028 (9)	0.0182 (9)	−0.0053 (9)
C15	0.0610 (12)	0.0463 (10)	0.0670 (13)	−0.0034 (9)	0.0132 (10)	−0.0087 (9)
C16	0.0609 (12)	0.0478 (10)	0.0474 (10)	0.0211 (9)	0.0050 (9)	−0.0035 (8)
C17	0.0436 (11)	0.0751 (14)	0.0766 (14)	0.0156 (10)	0.0139 (10)	−0.0211 (11)
C18	0.0382 (10)	0.0673 (12)	0.0728 (14)	0.0025 (9)	0.0107 (9)	−0.0252 (10)
N19	0.0874 (14)	0.0598 (11)	0.0644 (12)	0.0304 (11)	0.0071 (10)	−0.0099 (9)
O1W	0.0554 (9)	0.0704 (9)	0.0539 (8)	0.0256 (7)	0.0187 (7)	0.0049 (7)

Geometric parameters (Å, º) top

O1—C12	1.420 (2)	C9—C12	1.534 (2)
O1—H1	0.95 (3)	C9—C10	1.540 (3)
O2—N19	1.217 (2)	C9—H9A	0.9800
O3—N19	1.216 (2)	C10—C11	1.527 (3)
N1—C2	1.294 (2)	C10—H10A	0.9700
N1—C8A	1.420 (2)	C10—H10B	0.9700
C2—N3	1.333 (2)	C11—H11A	0.9700
C2—C9	1.513 (2)	C11—H11B	0.9700
N3—C4	1.451 (2)	C12—C13	1.515 (2)
N3—C11	1.459 (2)	C12—H12A	0.9800
C4—C4A	1.505 (3)	C13—C14	1.380 (2)
C4—H4A	0.9700	C13—C18	1.382 (2)
C4—H4B	0.9700	C14—C15	1.381 (3)
C4A—C5	1.387 (3)	C14—H14A	0.9300
C4A—C8A	1.398 (2)	C15—C16	1.366 (3)
C5—C6	1.380 (3)	C15—H15A	0.9300
C5—H5A	0.9300	C16—C17	1.374 (3)
C6—C7	1.372 (3)	C16—N19	1.471 (2)
C6—H6A	0.9300	C17—C18	1.377 (3)
C7—C8	1.383 (3)	C17—H17A	0.9300
C7—H7A	0.9300	C18—H18A	0.9300
C8—C8A	1.388 (3)	O1W—H1W	0.86 (3)
C8—H8A	0.9300	O1W—H2W	0.89 (3)

C12—O1—H1	108.1 (17)	C11—C10—H10A	110.5
C2—N1—C8A	115.94 (14)	C9—C10—H10A	110.5
N1—C2—N3	126.93 (16)	C11—C10—H10B	110.5
N1—C2—C9	123.07 (15)	C9—C10—H10B	110.5
N3—C2—C9	109.97 (15)	H10A—C10—H10B	108.7
C2—N3—C4	123.89 (15)	N3—C11—C10	104.22 (14)
C2—N3—C11	114.25 (15)	N3—C11—H11A	110.9
C4—N3—C11	121.82 (14)	C10—C11—H11A	110.9
N3—C4—C4A	110.24 (14)	N3—C11—H11B	110.9
N3—C4—H4A	109.6	C10—C11—H11B	110.9
C4A—C4—H4A	109.6	H11A—C11—H11B	108.9
N3—C4—H4B	109.6	O1—C12—C13	112.19 (14)
C4A—C4—H4B	109.6	O1—C12—C9	107.19 (13)
H4A—C4—H4B	108.1	C13—C12—C9	113.63 (14)
C5—C4A—C8A	118.79 (18)	O1—C12—H12A	107.9
C5—C4A—C4	120.53 (17)	C13—C12—H12A	107.9
C8A—C4A—C4	120.68 (16)	C9—C12—H12A	107.9
C6—C5—C4A	121.3 (2)	C14—C13—C18	118.21 (17)
C6—C5—H5A	119.4	C14—C13—C12	123.21 (15)
C4A—C5—H5A	119.4	C18—C13—C12	118.53 (16)
C7—C6—C5	119.88 (19)	C13—C14—C15	120.99 (17)
C7—C6—H6A	120.1	C13—C14—H14A	119.5
C5—C6—H6A	120.1	C15—C14—H14A	119.5
C6—C7—C8	119.8 (2)	C16—C15—C14	119.12 (18)
C6—C7—H7A	120.1	C16—C15—H15A	120.4
C8—C7—H7A	120.1	C14—C15—H15A	120.4
C7—C8—C8A	120.87 (19)	C15—C16—C17	121.54 (17)
C7—C8—H8A	119.6	C15—C16—N19	120.08 (18)
C8A—C8—H8A	119.6	C17—C16—N19	118.35 (18)
C8—C8A—C4A	119.37 (17)	C16—C17—C18	118.45 (18)
C8—C8A—N1	118.37 (16)	C16—C17—H17A	120.8
C4A—C8A—N1	122.25 (16)	C18—C17—H17A	120.8
C2—C9—C12	109.34 (14)	C17—C18—C13	121.65 (18)
C2—C9—C10	103.65 (14)	C17—C18—H18A	119.2
C12—C9—C10	114.74 (15)	C13—C18—H18A	119.2
C2—C9—H9A	109.6	O3—N19—O2	123.18 (19)
C12—C9—H9A	109.6	O3—N19—C16	118.45 (19)
C10—C9—H9A	109.6	O2—N19—C16	118.4 (2)
C11—C10—C9	106.12 (15)	H1W—O1W—H2W	118 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the N1,C2,N3,C4,C4A,C8A and C4A,C5–C8,C8A rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···N1	0.86 (2)	1.89 (3)	2.751 (2)	174 (2)
O1W—H2W···O1ⁱ	0.89 (3)	1.97 (3)	2.835 (2)	162 (2)
O1—H1···O1Wⁱⁱ	0.95 (4)	1.71 (3)	2.660 (2)	173 (3)
C4—H4B···Cg1ⁱⁱⁱ	0.97	2.92	3.634 (2)	131
C11—H11A···Cg2ⁱⁱⁱ	0.97	2.94	3.681 (2)	134

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₇N₃O₃·H₂O
M_r	341.36
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	6.2459 (7), 11.4629 (11), 11.8400 (13)
α, β, γ (°)	91.932 (8), 95.589 (9), 104.747 (9)
V (Å³)	814.37 (15)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	0.83
Crystal size (mm)	0.50 × 0.35 × 0.15

Data collection
Diffractometer	Oxford Diffraction Xcalibur Ruby diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.793, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	4649, 2867, 2076
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.124, 1.03
No. of reflections	2867
No. of parameters	238
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.20

Computer programs: CrysAlis PRO, (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the N1,C2,N3,C4,C4A,C8A and C4A,C5–C8,C8A rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···N1	0.86 (2)	1.89 (3)	2.751 (2)	174 (2)
O1W—H2W···O1ⁱ	0.89 (3)	1.97 (3)	2.835 (2)	162 (2)
O1—H1···O1Wⁱⁱ	0.95 (4)	1.71 (3)	2.660 (2)	173 (3)
C4—H4B···Cg1ⁱⁱⁱ	0.97	2.92	3.634 (2)	131
C11—H11A···Cg2ⁱⁱⁱ	0.97	2.94	3.681 (2)	134

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

Acknowledgements

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

References

Al-Shamma, A., Drake, S., Flynn, D. L., Mitscher, L. A., Park, Y. H., Rao, G. S. R., Simpson, A., Swayze, J. K., Veysoglu, T. & Wu, S. T. S. (1981). J. Nat. Prod. 44, 745–747. CrossRef CAS PubMed Web of Science Google Scholar
Jahng, K. C., Kim, S. I., Kim, D. H., Seo, C. S., Son, J.-K., Lee, S. H., Lee, E. S. & Jahng, Y. (2008). Chem. Pharm. Bull. 56, 607–609. Web of Science CrossRef PubMed CAS Google Scholar
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Shakhidoyatov, Kh. M. (1988). Quinazol-4-ones and Their Biological Activity, pp. 99–104. Tashkent: Fan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yunusov, S. Yu., Tulyaganov, N., Telezhenetskaya, M. V., Sadritdinov, F. & Khashimov, Kh. (1978). USSR Patent No. 605614; `Anticholinesterase agent', Byull. Izobret. No.17. Google Scholar

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Volume 67| Part 7| July 2011| Page o1680

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

(4-Nitro­phenyl)(1,2,3,9-tetra­hydro­pyrrolo[2,1-b]quinazolin-3-yl)methanol monohydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(4-Nitrophenyl)(1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-3-yl)methanol monohydrate