3-Hydr­oxy-1,2,3,9-tetra­hydro­pyrrolo[2,1-b]quinazolin-4-ium chloride dihydrate: (+)-vasicinol hydro­chloride dihydrate from Peganum harmala L

Khan, A.M.; Abbas, G.; Qureshi, R.A.; Khan, U.; Ghufran, M.A.; Stoeckli-Evans, H.

doi:10.1107/S1600536809003766

organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Pages o474-o475

doi:10.1107/S1600536809003766

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3-Hydroxy-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-4-ium chloride dihydrate: (+)-vasicinol hydrochloride dihydrate from Peganum harmala L

Amir Muhammad Khan,^a Ghulam Abbas,^b Rizwana Aleem Qureshi,^a ^* Uzma Khan,^a Muhammad Asad Ghufran ^a and Helen Stoeckli-Evans ^c

^aDepartment of Plant Sciences, Quaid-i-Azam University, Islamabad, Pakistan, ^bWell Department Services, Oil and Gas Development Company Ltd, Islamabad, Pakistan, and ^cInstitute of Physics, University of Neuchâtel, Rue Emile-Argand 11, CH-2009 Neuchâtel, Switzerland
^*Correspondence e-mail: rizwanaaleem@yahoo.com

(Received 26 January 2009; accepted 31 January 2009; online 6 February 2009)

The title compound, C₁₁H₁₃N₂O⁺·Cl⁻·2H₂O, the dihydrate of (+)-vasicinol hydrochloride, is a pyrrolidinoquinazoline alkaloid. It was isolated from the ethyl acetate fraction of the leaves of Peganum harmala L. The pyrrolidine ring has an envelope conformation with the C atom at position 2 acting as the flap and the C atom at position 3, carrying the hydroxyl substituent, has an S configuration. The absolute configuration was determined as a result of the anomalous scattering of the Cl atom. In the crystal structure, molecules stack along the a axis, connected to one another via intermolecular O—H⋯Cl and N—H⋯Cl hydrogen bonds, forming approximately triangular-shaped R₂¹(7) rings, and O—H⋯Cl and O—H⋯O hydrogen bonds, forming pentagonal-shaped R₅⁴(10) rings. The overall effect is a ribbon-like arrangement running parallel to the a axis.

Related literature

For the isolation (+)-vasicinol and the crystal structure analysis of (+)-vasicinol hydrobromide, see: Joshi et al. (1996 ). For general background on pyrrolidino-quinazoline alkaloids and their structures, see: Szulzewsky et al. (1976 ): Openshaw (1953 ); Bailey (1986 ); Rizk (1986 ); Tashkhodzhaev et al. (1995 ); Turgunov et al. (1995 ). For a study on the anti-Leishmaniasis activity of (+)-vasicinol hydrochloride dihydrate, see: Misra et al. (2008 ). For further related literature on natural products, see: Hilal & Youngken (1983 ); Mirzakhmedov et al. (1975 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₁H₁₃N₂O⁺·Cl⁻·2H₂O
M_r = 260.72
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.0386 (6) Å
b = 9.5752 (10) Å
c = 18.4041 (18) Å
V = 1240.4 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 173 (2) K
0.42 × 0.19 × 0.11 mm

Data collection

Stoe IPDS diffractometer
Absorption correction: none
8680 measured reflections
2422 independent reflections
1834 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.061
S = 0.90
2422 reflections
216 parameters
2 restraints
All H-atom parameters refined
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.14 e Å⁻³
Absolute structure: Flack (1983 ), 984 Friedel pairs
Flack parameter: 0.004 (64)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯Cl1ⁱ	0.90 (2)	2.20 (2)	3.086 (2)	171 (2)
N9—H9N⋯Cl1ⁱ	0.83 (2)	2.35 (2)	3.155 (2)	167 (2)
O1W—H1WA⋯Cl1ⁱⁱ	0.83 (4)	2.39 (4)	3.204 (2)	167 (3)
O1W—H1WB⋯O2Wⁱⁱ	0.79 (4)	1.96 (4)	2.720 (3)	162 (4)
O2W—H2WA⋯Cl1ⁱⁱⁱ	0.83 (4)	2.35 (4)	3.173 (2)	175 (3)
O2W—H2WB⋯O1W^iv	0.89 (3)	1.83 (3)	2.718 (3)	179 (5)
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x-1, y, z; (iv) $[-x+{\script{1\over 2}}, -y+1, z+{\script{1\over 2}}]$ .

Data collection: EXPOSE in IPDS-I (Stoe & Cie, 2000 ); cell refinement: CELL in IPDS-I; data reduction: INTEGRATE in IPDS-I; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809003766/lh2765sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809003766/lh2765Isup2.hkl

checkCIF report

Comment top

Peganum harmala L is a member of the family Zygophyllaceae (Hilal and Youngken, 1983). This plant is commonly distributed in the Attock District, Islamabad, including the Margalla Hills. Several alkaloids have been isolated from the seeds and roots of this plant and have been identified as chemicals with a β-carboline structure, such as harmine, harmaline, harmalol, and harman (Bailey, 1986; Rizk, 1986), or with a quinazoline structure, such as vasicine and vasicinon (Openshaw, 1953; Bailey, 1986; Joshi et al., 1996). Here we report on the crystal structure of the title compound, the dihydrate of (+)Vasicinol hydrochloride. It is a pyrrolidino-quinazoline alkaloid and was isolated from the ethylacetate fraction of the leaves of Peganum harmala L, collected from the Margalla Hills, Islamabad.

The molecular structure of the title compound is shown in Fig. 1. Dimensions are similar to those observed in other pyrrolidino-quinazoline alkaloids (Joshi et al., 1996; Tashkhodzhaev et al., 1995; Turgunov et al., 1995; Szulzewsky et al., 1976). The title compound crystallizes in the non-centrosymmetric orthorhombic space group P2₁2₁2₁. The crystal structure of (+)-Vasicinol hydrobromide has been reported previously (Joshi et al., 1996), and crystallizes in the non-centrosymmetric monoclinic space group P2₁, with two independent molecules per asymmetric unit.

The pyrrolidine ring has an envelope conformation on atom C2; the puckering parameters (Cremer & Pople, 1975) are Q(2) = 0.243 (2) Å, and ϕ(2) = 253.8 (5)°. The carbon atom carrying the hydroxyl substituent, atom C3, has a S-configuration. The absolute configuration of the title compound was determined as a result of the anomalous scattering of the Cl-atom.

In the crystal the molecules stacks up the a axis and are connected to one another via a series of O—H···Cl, N—H···Cl hydrogen bonds, with approximately triangular-shaped R¹₂(7) rings (Bernstein et al., 1995) and O—H···Cl and O—H···O hydrogen bonds, forming pentagonal-shaped R₅⁴(10) rings [see Fig. 2 and Table 1]. In this way a ribon-like arrangement is formed running parallel to the a axis. The same triangular arrangement, involving O—H···halide^- and N—H···halide^- hydrogen bonds, is also observed in the crystal packing of (+)-Vasicine hydrobromide (Fig. 3; Joshi et al., 1996).

Related literature top

For the isolation (+)-vasicinol and the crystal structure analysis of (+)-vasicinol hydrobromide, see: Joshi et al. (1996). For general background on pyrrolidino-quinazoline alkaloids and their structures, see: Szulzewsky et al. (1976): Openshaw (1953); Bailey (1986); Rizk (1986); Tashkhodzhaev et al. (1995); Turgunov et al. (1995). For a study on the anti-Leishmaniasis activity of (+)-vasicinol hydrochloride dihydrate, see: Misra et al. (2008). For further related literature on natural products, see: Hilal & Youngken (1983); Mirzakhmedov et al. (1975). For hydorgen-bond motifs, see: Bernstein et al. (1995). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

Peganum harmala L is a member of the family Zygophyllaceae (Hilal & Youngken, 1983). This plant is commonly distributed in the Attock District, Islamabad, including the Margalla Hills, Gilgit: Chilas, Yasin, Gupis, Phunder, Hunza, Skardu. The leaves of the plant were collected from the Margalla Hills, Islamabad and the sample was deposited in the herbarium of Quaid-i-Azam University (ISL) under the accession No. 123774 and 123775. The air dried leaves were powdered and extracted three times with methanol. The extracts were and concentrated to a semi-solid mass. Water was added to this semi-solid mass to form a paste. The extract was then fractioned using different solvents according to their increasing polarity. The title compound was isolated from the ethylacetate fraction of the leaves of Peganum harmala L as colourless rod-like crystals.

Computing details top

Data collection: EXPOSE in IPDS-I (Stoe & Cie, 2000); cell refinement: CELL in IPDS-I (Stoe & Cie, 2000); data reduction: INTEGRATE in IPDS-I (Stoe & Cie, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atomic numbering scheme and displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. View along the c direction of the crystal packing of the title compound, showing the formation of the triangular-shaped [R¹₂(7)], and pentagonal-shaped [R₅⁴(10)] rings of hydrogen bonds (dashed blue lines; Cl^- green ball; H-atoms not involved in hydrogen bonding have been removed for clarity).
	Fig. 3. View along the a axis of the crystal packing of (+)-Vasicinol hydrobromide (Joshi et al., 1996), showing the formation of the trianglular-shaped [R¹₂(7)] rings of hydrogen bonds [Br^- purple ball; H-atoms not involved in hydrogen bonding have been removed for clarity].

3-Hydroxy-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-4-ium chloride dihydrate top

Crystal data top

C₁₁H₁₃N₂O⁺·Cl⁻·2H₂O	F(000) = 552
M_r = 260.72	D_x = 1.396 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6244 reflections
a = 7.0386 (6) Å	θ = 2.2–25.9°
b = 9.5752 (10) Å	µ = 0.31 mm⁻¹
c = 18.4041 (18) Å	T = 173 K
V = 1240.4 (2) Å³	Rod, colourless
Z = 4	0.42 × 0.19 × 0.11 mm

Data collection top

Stoe IPDS diffractometer	1834 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.034
Graphite monochromator	θ_max = 26.1°, θ_min = 2.2°
phi rotation scans	h = −8→8
8680 measured reflections	k = −11→11
2422 independent reflections	l = −22→22

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)] = 0.029	All H-atom parameters refined
wR(F²) = 0.061	w = 1/[σ²(F_o²) + (0.033P)²] where P = (F_o² + 2F_c²)/3
S = 0.90	(Δ/σ)_max < 0.001
2422 reflections	Δρ_max = 0.20 e Å⁻³
216 parameters	Δρ_min = −0.14 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 984 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.004 (64)

Crystal data top

C₁₁H₁₃N₂O⁺·Cl⁻·2H₂O	V = 1240.4 (2) Å³
M_r = 260.72	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.0386 (6) Å	µ = 0.31 mm⁻¹
b = 9.5752 (10) Å	T = 173 K
c = 18.4041 (18) Å	0.42 × 0.19 × 0.11 mm

Data collection top

Stoe IPDS diffractometer	1834 reflections with I > 2σ(I)
8680 measured reflections	R_int = 0.034
2422 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	All H-atom parameters refined
wR(F²) = 0.061	Δρ_max = 0.20 e Å⁻³
S = 0.90	Δρ_min = −0.14 e Å⁻³
2422 reflections	Absolute structure: Flack (1983), 984 Friedel pairs
216 parameters	Absolute structure parameter: 0.004 (64)
2 restraints

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.3510 (2)	0.15059 (15)	0.24928 (8)	0.0409 (5)
N9	0.2235 (3)	0.16767 (15)	0.09484 (8)	0.0249 (5)
N10	0.2348 (2)	0.40126 (14)	0.12323 (8)	0.0246 (5)
C1	0.2373 (4)	0.4955 (2)	0.18629 (12)	0.0348 (8)
C2	0.2861 (4)	0.3982 (2)	0.24882 (11)	0.0348 (7)
C3	0.2264 (4)	0.2536 (2)	0.22362 (10)	0.0280 (7)
C4	0.2242 (3)	0.0847 (2)	−0.02920 (11)	0.0310 (7)
C5	0.2242 (3)	0.1121 (3)	−0.10295 (10)	0.0373 (7)
C6	0.2232 (4)	0.2484 (3)	−0.12768 (11)	0.0398 (8)
C7	0.2228 (3)	0.3570 (2)	−0.07828 (10)	0.0339 (7)
C8	0.2231 (4)	0.45209 (19)	0.04834 (10)	0.0287 (7)
C11	0.2303 (3)	0.27062 (18)	0.14208 (9)	0.0223 (6)
C12	0.2237 (3)	0.33226 (19)	−0.00429 (9)	0.0253 (6)
C13	0.2242 (3)	0.19435 (18)	0.01937 (9)	0.0227 (6)
O1W	0.4964 (3)	0.7633 (3)	0.06429 (11)	0.0639 (8)
O2W	0.1191 (3)	0.2477 (2)	0.42346 (11)	0.0598 (8)
Cl1	0.80565 (8)	0.38150 (5)	0.32092 (3)	0.0358 (2)
H1A	0.329 (3)	0.563 (2)	0.1789 (12)	0.033 (6)*
H1B	0.113 (4)	0.540 (2)	0.1877 (14)	0.049 (7)*
H1O	0.298 (4)	0.071 (2)	0.2333 (13)	0.0610*
H2A	0.225 (4)	0.422 (2)	0.2921 (12)	0.038 (6)*
H2B	0.431 (3)	0.395 (2)	0.2595 (11)	0.040 (6)*
H3	0.095 (3)	0.231 (2)	0.2387 (11)	0.036 (6)*
H4	0.233 (3)	−0.012 (2)	−0.0084 (10)	0.034 (6)*
H5	0.222 (4)	0.034 (2)	−0.1392 (12)	0.053 (7)*
H6	0.224 (3)	0.266 (2)	−0.1810 (13)	0.047 (6)*
H7	0.217 (4)	0.454 (2)	−0.0961 (12)	0.051 (7)*
H8A	0.108 (3)	0.502 (2)	0.0441 (11)	0.029 (6)*
H8B	0.331 (3)	0.517 (2)	0.0407 (11)	0.033 (6)*
H9N	0.211 (4)	0.0872 (17)	0.1102 (11)	0.0370*
H1WA	0.432 (5)	0.792 (4)	0.099 (2)	0.0960*
H1WB	0.603 (5)	0.764 (4)	0.077 (2)	0.0960*
H2WA	0.033 (5)	0.282 (4)	0.3988 (19)	0.0900*
H2WB	0.081 (5)	0.245 (4)	0.4695 (18)	0.0900*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0538 (11)	0.0371 (9)	0.0319 (8)	0.0022 (7)	−0.0108 (7)	0.0022 (7)
N9	0.0323 (11)	0.0191 (7)	0.0233 (8)	−0.0015 (8)	−0.0018 (8)	0.0007 (7)
N10	0.0296 (11)	0.0206 (8)	0.0235 (7)	0.0004 (8)	−0.0027 (7)	0.0010 (6)
C1	0.0445 (17)	0.0241 (10)	0.0357 (11)	−0.0014 (10)	0.0015 (12)	−0.0078 (9)
C2	0.0439 (15)	0.0338 (10)	0.0268 (10)	−0.0057 (12)	0.0001 (11)	−0.0084 (9)
C3	0.0337 (16)	0.0272 (10)	0.0230 (10)	−0.0018 (10)	0.0003 (9)	0.0000 (8)
C4	0.0307 (14)	0.0319 (11)	0.0305 (10)	0.0038 (9)	−0.0018 (10)	−0.0054 (8)
C5	0.0312 (14)	0.0536 (12)	0.0272 (10)	0.0024 (13)	−0.0031 (9)	−0.0119 (11)
C6	0.0360 (15)	0.0600 (14)	0.0234 (10)	0.0003 (13)	−0.0011 (11)	0.0050 (10)
C7	0.0318 (13)	0.0429 (13)	0.0270 (10)	0.0017 (11)	−0.0002 (9)	0.0090 (9)
C8	0.0317 (14)	0.0253 (10)	0.0292 (11)	−0.0001 (11)	−0.0030 (10)	0.0075 (8)
C11	0.0194 (13)	0.0225 (9)	0.0249 (9)	0.0014 (8)	0.0003 (8)	−0.0017 (8)
C12	0.0182 (12)	0.0323 (9)	0.0253 (9)	0.0002 (9)	−0.0014 (9)	0.0027 (8)
C13	0.0199 (12)	0.0281 (9)	0.0200 (9)	−0.0006 (8)	−0.0001 (8)	0.0004 (7)
O1W	0.0428 (12)	0.1035 (16)	0.0453 (11)	0.0043 (12)	0.0030 (9)	−0.0184 (11)
O2W	0.0432 (13)	0.0885 (15)	0.0477 (11)	0.0093 (11)	0.0014 (9)	0.0226 (11)
Cl1	0.0414 (3)	0.0279 (2)	0.0380 (3)	0.0034 (2)	0.0001 (3)	−0.0046 (2)

Geometric parameters (Å, º) top

O1—C3	1.402 (3)	C5—C6	1.382 (4)
O1—H1O	0.90 (2)	C6—C7	1.381 (3)
O1W—H1WB	0.79 (4)	C7—C12	1.382 (2)
O1W—H1WA	0.83 (4)	C8—C12	1.502 (3)
O2W—H2WA	0.83 (4)	C12—C13	1.391 (2)
O2W—H2WB	0.89 (3)	C1—H1B	0.97 (3)
N9—C13	1.412 (2)	C1—H1A	0.92 (2)
N9—C11	1.315 (2)	C2—H2A	0.93 (2)
N10—C11	1.299 (2)	C2—H2B	1.04 (2)
N10—C8	1.464 (2)	C3—H3	0.99 (2)
N10—C1	1.470 (3)	C4—H4	1.004 (19)
N9—H9N	0.825 (17)	C5—H5	1.00 (2)
C1—C2	1.520 (3)	C6—H6	1.00 (2)
C2—C3	1.519 (3)	C7—H7	0.99 (2)
C3—C11	1.510 (2)	C8—H8A	0.94 (2)
C4—C5	1.382 (3)	C8—H8B	0.99 (2)
C4—C13	1.379 (3)

C3—O1—H1O	103.1 (16)	C4—C13—C12	121.34 (16)
H1WA—O1W—H1WB	107 (4)	N10—C1—H1A	108.8 (14)
H2WA—O2W—H2WB	108 (3)	C2—C1—H1B	116.8 (15)
C11—N9—C13	120.96 (15)	N10—C1—H1B	106.2 (14)
C1—N10—C11	112.38 (15)	C2—C1—H1A	112.5 (13)
C1—N10—C8	122.67 (14)	H1A—C1—H1B	109.0 (18)
C8—N10—C11	124.78 (15)	C1—C2—H2B	112.5 (11)
C13—N9—H9N	120.4 (14)	C3—C2—H2A	110.8 (13)
C11—N9—H9N	118.5 (14)	H2A—C2—H2B	107 (2)
N10—C1—C2	102.95 (15)	C3—C2—H2B	107.6 (11)
C1—C2—C3	105.36 (17)	C1—C2—H2A	113.1 (13)
O1—C3—C2	111.4 (2)	O1—C3—H3	109.7 (12)
O1—C3—C11	113.54 (17)	C11—C3—H3	108.6 (12)
C2—C3—C11	101.54 (15)	C2—C3—H3	111.9 (11)
C5—C4—C13	119.47 (19)	C13—C4—H4	117.1 (11)
C4—C5—C6	120.2 (2)	C5—C4—H4	123.3 (11)
C5—C6—C7	119.61 (19)	C4—C5—H5	120.8 (12)
C6—C7—C12	121.29 (19)	C6—C5—H5	119.0 (12)
N10—C8—C12	110.68 (14)	C7—C6—H6	121.4 (11)
N9—C11—C3	125.13 (16)	C5—C6—H6	119.0 (11)
N10—C11—C3	111.72 (15)	C12—C7—H7	119.3 (13)
N9—C11—N10	123.11 (16)	C6—C7—H7	119.4 (13)
C8—C12—C13	121.58 (15)	N10—C8—H8B	107.4 (12)
C7—C12—C8	120.30 (16)	N10—C8—H8A	107.1 (12)
C7—C12—C13	118.12 (16)	H8A—C8—H8B	109.2 (17)
N9—C13—C4	119.99 (16)	C12—C8—H8A	109.6 (12)
N9—C13—C12	118.67 (15)	C12—C8—H8B	112.7 (12)

C13—N9—C11—N10	1.2 (3)	O1—C3—C11—N10	−135.24 (18)
C13—N9—C11—C3	178.7 (2)	C2—C3—C11—N9	166.7 (2)
C11—N9—C13—C4	177.6 (2)	C2—C3—C11—N10	−15.5 (3)
C11—N9—C13—C12	−2.8 (3)	C13—C4—C5—C6	−0.3 (3)
C8—N10—C1—C2	−170.1 (2)	C5—C4—C13—N9	179.8 (2)
C11—N10—C1—C2	14.5 (3)	C5—C4—C13—C12	0.2 (3)
C1—N10—C8—C12	179.9 (2)	C4—C5—C6—C7	0.2 (4)
C11—N10—C8—C12	−5.3 (3)	C5—C6—C7—C12	0.1 (4)
C1—N10—C11—N9	178.6 (2)	C6—C7—C12—C8	−180.0 (2)
C1—N10—C11—C3	0.7 (3)	C6—C7—C12—C13	−0.3 (3)
C8—N10—C11—N9	3.3 (3)	N10—C8—C12—C7	−176.89 (19)
C8—N10—C11—C3	−174.5 (2)	N10—C8—C12—C13	3.4 (3)
N10—C1—C2—C3	−23.3 (3)	C7—C12—C13—N9	−179.5 (2)
C1—C2—C3—O1	144.52 (19)	C7—C12—C13—C4	0.1 (3)
C1—C2—C3—C11	23.3 (3)	C8—C12—C13—N9	0.2 (3)
O1—C3—C11—N9	47.0 (3)	C8—C12—C13—C4	179.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···Cl1ⁱ	0.90 (2)	2.20 (2)	3.086 (2)	171 (2)
N9—H9N···Cl1ⁱ	0.83 (2)	2.35 (2)	3.155 (2)	167 (2)
O1W—H1WA···Cl1ⁱⁱ	0.83 (4)	2.39 (4)	3.204 (2)	167 (3)
O1W—H1WB···O2Wⁱⁱ	0.79 (4)	1.96 (4)	2.720 (3)	162 (4)
O2W—H2WA···Cl1ⁱⁱⁱ	0.83 (4)	2.35 (4)	3.173 (2)	175 (3)
O2W—H2WB···O1W^iv	0.89 (3)	1.83 (3)	2.718 (3)	179 (5)

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

Experimental details

Crystal data
Chemical formula	C₁₁H₁₃N₂O⁺·Cl⁻·2H₂O
M_r	260.72
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	173
a, b, c (Å)	7.0386 (6), 9.5752 (10), 18.4041 (18)
V (Å³)	1240.4 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.42 × 0.19 × 0.11

Data collection
Diffractometer	Stoe IPDS diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8680, 2422, 1834
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.061, 0.90
No. of reflections	2422
No. of parameters	216
No. of restraints	2
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.14
Absolute structure	Flack (1983), 984 Friedel pairs
Absolute structure parameter	0.004 (64)

Computer programs: EXPOSE in IPDS-I (Stoe & Cie, 2000), CELL in IPDS-I (Stoe & Cie, 2000), INTEGRATE in IPDS-I (Stoe & Cie, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···Cl1ⁱ	0.90 (2)	2.20 (2)	3.086 (2)	171 (2)
N9—H9N···Cl1ⁱ	0.83 (2)	2.35 (2)	3.155 (2)	167 (2)
O1W—H1WA···Cl1ⁱⁱ	0.83 (4)	2.39 (4)	3.204 (2)	167 (3)
O1W—H1WB···O2Wⁱⁱ	0.79 (4)	1.96 (4)	2.720 (3)	162 (4)
O2W—H2WA···Cl1ⁱⁱⁱ	0.83 (4)	2.35 (4)	3.173 (2)	175 (3)
O2W—H2WB···O1W^iv	0.89 (3)	1.83 (3)	2.718 (3)	179 (5)

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

References

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Volume 65| Part 3| March 2009| Pages o474-o475

doi:10.1107/S1600536809003766

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

3-Hydr­­oxy-1,2,3,9-tetra­hydro­pyrrolo[2,1-b]quinazolin-4-ium chloride dihydrate: (+)-vasicinol hydro­chloride dihydrate from Peganum harmala L

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

3-Hydroxy-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-4-ium chloride dihydrate: (+)-vasicinol hydrochloride dihydrate from Peganum harmala L