1-(1-Hy­droxy­eth­yl)-7,8-dihydro­indolo[2,3-a]pyridine­[3,4-g]quinolizin-5(13H)-one (angustoline) monohydrate from Nauclea subdita (Rubiaceae)

Liew, S.Y.; Mukhtar, M.R.; Awang, K.; Mustafa, M.R.; Ng, S.W.

doi:10.1107/S1600536811022768

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Pages o1727-o1728

doi:10.1107/S1600536811022768

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1-(1-Hydroxyethyl)-7,8-dihydroindolo[2,3-a]pyridine[3,4-g]quinolizin-5(13H)-one (angustoline) monohydrate from Nauclea subdita (Rubiaceae)

Sook Yee Liew,^a Mat Ropi Mukhtar,^a Khalijah Awang,^a Mohd Rais Mustafa ^b and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^bDepartment of Pharmacology, Faculty of Medicine, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 12 June 2011; accepted 13 June 2011; online 18 June 2011)

The title compound (trivial name: angustoline monohydrate), C₂₀H₁₇N₃O₂·H₂O, features a fused-ring system formed by one five- and four six-membered rings. The nearly planar benzimidazole portion (r.m.s. deviation = 0.008 Å) and the nearly planar 2,7-naphthyridin-1-one portion (r.m.s. deviation = 0.022 Å) of the fused-ring system are slightly twisted, with a dihedral angle of 9.47 (8)°, owing to the tetrahedral nature of the two methylene linkages in the central six-membered ring. The secondary N atom acts as a hydrogen-bond donor to the water molecule of crystallization. In the crystal, the amino and hydroxy groups, and the water molecule are engaged in hydrogen bonding, generating a three-dimensional network.

Related literature

For the isolation of the title compound from other plants, see: Abreu & Pereira (1998 , 2001 ); Au et al. (1973 ); Carte et al. (1990 ); Erdelmeier et al. (1992 ); Fan et al. (2010 ); Hotellier et al. (1975 ); Kakuguchi et al. (2009 ); Lin et al. (1988 ); Sun et al. (2008 ); Xuan et al. (2007 ); Zeches et al. (1985 ).

Experimental

Crystal data

C₂₀H₁₇N₃O₂·H₂O
M_r = 349.38
Monoclinic, P 2₁
a = 8.8350 (3) Å
b = 6.7002 (2) Å
c = 14.7347 (4) Å
β = 103.117 (3)°
V = 849.48 (4) Å³
Z = 2
Cu Kα radiation
μ = 0.76 mm⁻¹
T = 100 K
0.30 × 0.03 × 0.03 mm

Data collection

Agilent SuperNova Dual with an Atlas detector diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.803, T_max = 0.978
6453 measured reflections
3252 independent reflections
3015 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.098
S = 1.02
3252 reflections
251 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.23 e Å⁻³
Absolute structure: Flack (1983 ), 1395 Friedel pairs
Flack parameter: 0.1 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N3ⁱ	0.97 (4)	1.77 (4)	2.732 (2)	171 (3)
O1w—H11⋯O1ⁱⁱ	0.85 (4)	2.08 (4)	2.928 (2)	169 (3)
O1w—H12⋯O2ⁱⁱⁱ	0.83 (4)	1.95 (4)	2.762 (2)	167 (3)
N1—H1⋯O1w	0.85 (3)	2.02 (3)	2.861 (2)	177 (2)
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+1]$ ; (ii) x+1, y, z; (iii) $[-x+2, y-{\script{1\over 2}}, -z+1]$ .

Data collection: CrysAlis PRO (Agilent, 2010); 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: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811022768/xu5242sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811022768/xu5242Isup2.hkl

checkCIF report

Comment top

The alkaloid angustoline has been isolated from a number of plants: Camptotheca acuminata (Carte et al., 1990; Lin et al., 1988), Nauclea latifolia (Kakuguchi et al., 2009; Hotellier et al., 1975), Nauclea officinalis (Fan et al., 2010; Sun et al., 2008; Xuan et al., 2007), Nauclea orientalis (Erdelmeier et al., 1992), Nauclea pobeguinii (Zeches et al., 1985), Sarcocephalus latifolius (Abreu & Pereira, 1998; 2001) and Strychnos angustiflora (Au et al., 1973).

The alkaloid is isolated in the crystalline form as a monohydrate (Scheme I). The planar benzimidazole portion and the planar 2,7-naphthyridin-1-one portion of the fused-ring system are slightly twisted [dihedral angle 9.47 (8)°] owing to the tetrahedral nature of the two methylene linkages (Fig. 1). The secondary N atom is hydrogen-bond donor to the water molecule. The amino and hydroxy groups, and the lattice water molecule are engaged in hydrogen bonding to furnish a three-dimensional network (Table 1).

Related literature top

For the isolation of the title compound from other plants, see: Abreu & Pereira (1998, 2001); Au et al. (1973); Carte et al. (1990); Erdelmeier et al. (1992); Fan et al. (2010); Hotellier et al. (1975); Kakuguchi et al. (2009); Lin et al. (1988); Sun et al. (2008); Xuan et al. (2007); Zeches et al. (1985).

Experimental top

Nauclea subdita (Rubiaceae) was collected from Bukit Kinta forest reserve, Chemor, Perak, Malaysia, and specimens were deposited at the Herbarium, Department of Chemistry, University of Malaya.

Dried and ground bark of Nauclea subdita (1.7 kg) was extracted with hexane (17 L) for 3 days. The hexane extract was concentrated under reduced pressure. The dried plant material was soaked in ammonium hydroxide for 2 h. It was further extracted with dichloromethane (17 L) for 3 days. The dichloromethane extract was concentrated under reduced pressure to give a crude alkaloid (7.1 g). A portion (6.0 g) was subjected to column chromatography on silica gel 60 GF₂₅₄ by using a step gradient of dichloromethane and methanol. One of the fractions when further purified by using dichloromethane/methanol (95:5) afforded the pure compound, whose formulation was established by NMR spectroscopic analysis.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₂₀H₁₇N₃O₂^.H₂O at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

1-(1-Hydroxyethyl)-7,8-dihydroindolo[2,3-a]pyridine[3,4- g]quinolizin-5(13H)-one monohydrate top

Crystal data top

C₂₀H₁₇N₃O₂·H₂O	F(000) = 368
M_r = 349.38	D_x = 1.366 Mg m⁻³
Monoclinic, P2₁	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2yb	Cell parameters from 3352 reflections
a = 8.8350 (3) Å	θ = 3.1–74.0°
b = 6.7002 (2) Å	µ = 0.76 mm⁻¹
c = 14.7347 (4) Å	T = 100 K
β = 103.117 (3)°	Prism, yellow
V = 849.48 (4) Å³	0.30 × 0.03 × 0.03 mm
Z = 2

Data collection top

Agilent SuperNova Dual with an Atlas detector diffractometer	3252 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	3015 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.027
Detector resolution: 10.4041 pixels mm^-1	θ_max = 74.2°, θ_min = 3.1°
ω scans	h = −11→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −7→8
T_min = 0.803, T_max = 0.978	l = −17→18
6453 measured reflections

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)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.098	w = 1/[σ²(F_o²) + (0.0647P)² + 0.0395P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
3252 reflections	Δρ_max = 0.29 e Å⁻³
251 parameters	Δρ_min = −0.23 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1395 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.1 (2)

Crystal data top

C₂₀H₁₇N₃O₂·H₂O	V = 849.48 (4) Å³
M_r = 349.38	Z = 2
Monoclinic, P2₁	Cu Kα radiation
a = 8.8350 (3) Å	µ = 0.76 mm⁻¹
b = 6.7002 (2) Å	T = 100 K
c = 14.7347 (4) Å	0.30 × 0.03 × 0.03 mm
β = 103.117 (3)°

Data collection top

Agilent SuperNova Dual with an Atlas detector diffractometer	3252 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	3015 reflections with I > 2σ(I)
T_min = 0.803, T_max = 0.978	R_int = 0.027
6453 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.098	Δρ_max = 0.29 e Å⁻³
S = 1.02	Δρ_min = −0.23 e Å⁻³
3252 reflections	Absolute structure: Flack (1983), 1395 Friedel pairs
251 parameters	Absolute structure parameter: 0.1 (2)
1 restraint

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

	x	y	z	U_iso*/U_eq
O1	0.33730 (17)	0.5046 (2)	0.78985 (11)	0.0309 (3)
O2	0.76411 (17)	0.6678 (2)	0.44802 (9)	0.0280 (3)
H2	0.677 (4)	0.578 (5)	0.429 (2)	0.061 (9)*
O1W	1.0970 (2)	0.2216 (3)	0.70030 (13)	0.0384 (4)
H11	1.157 (4)	0.316 (6)	0.725 (2)	0.060 (10)*
H12	1.125 (4)	0.196 (6)	0.652 (2)	0.063 (10)*
N1	0.89459 (18)	0.0009 (2)	0.78964 (11)	0.0210 (3)
H1	0.953 (3)	0.071 (4)	0.7637 (15)	0.022 (6)*
N2	0.54310 (19)	0.2982 (2)	0.79266 (12)	0.0234 (3)
N3	0.4603 (2)	0.8811 (3)	0.59777 (12)	0.0280 (4)
C1	0.9248 (2)	−0.1772 (3)	0.83570 (12)	0.0212 (4)
C2	1.0553 (2)	−0.3025 (3)	0.84619 (13)	0.0238 (4)
H2A	1.1403	−0.2694	0.8195	0.029*
C3	1.0547 (2)	−0.4757 (3)	0.89683 (12)	0.0245 (4)
H3	1.1405	−0.5644	0.9040	0.029*
C4	0.9304 (2)	−0.5250 (3)	0.93830 (12)	0.0256 (4)
H4	0.9340	−0.6452	0.9729	0.031*
C5	0.8035 (2)	−0.3999 (3)	0.92892 (12)	0.0236 (4)
H5	0.7204	−0.4328	0.9574	0.028*
C6	0.7989 (2)	−0.2238 (3)	0.87687 (12)	0.0214 (4)
C7	0.6920 (2)	−0.0637 (3)	0.85452 (13)	0.0218 (4)
C8	0.5381 (2)	−0.0264 (3)	0.87749 (14)	0.0250 (4)
H8A	0.5377	−0.0813	0.9398	0.030*
H8B	0.4545	−0.0924	0.8311	0.030*
C9	0.5108 (2)	0.1974 (3)	0.87643 (14)	0.0280 (4)
H9A	0.4015	0.2229	0.8789	0.034*
H9B	0.5781	0.2566	0.9330	0.034*
C10	0.6769 (2)	0.2496 (3)	0.76131 (13)	0.0209 (4)
C11	0.7537 (2)	0.0699 (3)	0.80190 (12)	0.0214 (4)
C12	0.7238 (2)	0.3627 (3)	0.69551 (13)	0.0205 (4)
H12A	0.8131	0.3245	0.6740	0.025*
C13	0.6401 (2)	0.5366 (3)	0.65911 (12)	0.0207 (4)
C14	0.5043 (2)	0.5833 (3)	0.69001 (13)	0.0224 (4)
C15	0.4529 (2)	0.4620 (3)	0.75959 (13)	0.0238 (4)
C16	0.4187 (2)	0.7539 (3)	0.65684 (13)	0.0250 (4)
H16	0.3263	0.7802	0.6775	0.030*
C17	0.5887 (2)	0.8336 (3)	0.56645 (13)	0.0274 (4)
H17	0.6179	0.9220	0.5230	0.033*
C18	0.6799 (2)	0.6681 (3)	0.59251 (12)	0.0230 (4)
C19	0.8136 (2)	0.6270 (3)	0.54537 (13)	0.0260 (4)
H19	0.8421	0.4826	0.5537	0.031*
C20	0.9565 (3)	0.7508 (4)	0.58426 (16)	0.0396 (5)
H20A	1.0380	0.7178	0.5514	0.059*
H20B	0.9938	0.7220	0.6508	0.059*
H20C	0.9306	0.8928	0.5758	0.059*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0278 (7)	0.0272 (7)	0.0445 (8)	0.0050 (6)	0.0228 (6)	0.0025 (6)
O2	0.0305 (7)	0.0321 (7)	0.0238 (7)	−0.0063 (6)	0.0114 (6)	0.0003 (6)
O1W	0.0409 (9)	0.0419 (10)	0.0405 (9)	−0.0122 (7)	0.0261 (7)	−0.0102 (7)
N1	0.0210 (7)	0.0209 (8)	0.0245 (7)	0.0005 (6)	0.0125 (6)	0.0017 (6)
N2	0.0229 (8)	0.0223 (8)	0.0300 (8)	0.0018 (6)	0.0161 (6)	0.0006 (6)
N3	0.0267 (9)	0.0310 (10)	0.0272 (8)	0.0079 (7)	0.0081 (7)	0.0055 (7)
C1	0.0232 (9)	0.0216 (9)	0.0197 (8)	−0.0019 (7)	0.0068 (7)	−0.0023 (7)
C2	0.0233 (9)	0.0278 (10)	0.0222 (8)	0.0038 (7)	0.0089 (7)	−0.0024 (7)
C3	0.0263 (9)	0.0255 (10)	0.0218 (8)	0.0061 (7)	0.0057 (7)	−0.0009 (7)
C4	0.0324 (10)	0.0217 (10)	0.0234 (9)	0.0005 (8)	0.0080 (8)	0.0014 (7)
C5	0.0268 (9)	0.0231 (9)	0.0233 (8)	−0.0033 (8)	0.0107 (7)	−0.0011 (7)
C6	0.0215 (8)	0.0225 (9)	0.0218 (8)	−0.0013 (7)	0.0081 (7)	−0.0036 (7)
C7	0.0232 (9)	0.0207 (9)	0.0243 (8)	−0.0015 (7)	0.0109 (7)	−0.0025 (7)
C8	0.0239 (9)	0.0218 (10)	0.0337 (10)	0.0013 (7)	0.0161 (7)	0.0023 (8)
C9	0.0323 (10)	0.0241 (10)	0.0344 (10)	0.0022 (8)	0.0222 (9)	0.0029 (8)
C10	0.0206 (8)	0.0194 (9)	0.0255 (9)	0.0002 (7)	0.0114 (7)	−0.0032 (7)
C11	0.0218 (8)	0.0205 (9)	0.0248 (8)	0.0004 (7)	0.0112 (7)	−0.0049 (7)
C12	0.0189 (8)	0.0222 (10)	0.0232 (8)	0.0002 (7)	0.0105 (7)	−0.0024 (7)
C13	0.0188 (8)	0.0248 (10)	0.0198 (8)	−0.0010 (7)	0.0070 (7)	−0.0036 (6)
C14	0.0204 (8)	0.0242 (9)	0.0240 (8)	−0.0003 (7)	0.0082 (7)	−0.0011 (7)
C15	0.0224 (9)	0.0214 (10)	0.0305 (9)	0.0003 (7)	0.0122 (7)	−0.0026 (7)
C16	0.0218 (9)	0.0287 (10)	0.0266 (9)	0.0021 (7)	0.0101 (7)	−0.0002 (8)
C17	0.0273 (10)	0.0328 (11)	0.0233 (9)	0.0028 (8)	0.0086 (8)	0.0062 (7)
C18	0.0223 (9)	0.0277 (10)	0.0201 (8)	−0.0006 (7)	0.0073 (7)	−0.0015 (8)
C19	0.0251 (9)	0.0320 (11)	0.0235 (8)	0.0017 (7)	0.0107 (7)	0.0020 (7)
C20	0.0277 (10)	0.0625 (15)	0.0319 (11)	−0.0070 (10)	0.0134 (8)	−0.0115 (10)

Geometric parameters (Å, º) top

O1—C15	1.237 (2)	C7—C11	1.375 (3)
O2—C19	1.428 (2)	C7—C8	1.495 (2)
O2—H2	0.97 (4)	C8—C9	1.518 (3)
O1W—H11	0.85 (4)	C8—H8A	0.9900
O1W—H12	0.83 (4)	C8—H8B	0.9900
N1—C1	1.369 (2)	C9—H9A	0.9900
N1—C11	1.378 (2)	C9—H9B	0.9900
N1—H1	0.85 (3)	C10—C12	1.366 (2)
N2—C15	1.379 (3)	C10—C11	1.443 (3)
N2—C10	1.402 (2)	C12—C13	1.419 (3)
N2—C9	1.490 (2)	C12—H12A	0.9500
N3—C16	1.328 (3)	C13—C14	1.412 (2)
N3—C17	1.356 (3)	C13—C18	1.421 (3)
C1—C2	1.406 (3)	C14—C16	1.396 (3)
C1—C6	1.418 (2)	C14—C15	1.459 (3)
C2—C3	1.380 (3)	C16—H16	0.9500
C2—H2A	0.9500	C17—C18	1.373 (3)
C3—C4	1.412 (3)	C17—H17	0.9500
C3—H3	0.9500	C18—C19	1.525 (2)
C4—C5	1.381 (3)	C19—C20	1.511 (3)
C4—H4	0.9500	C19—H19	1.0000
C5—C6	1.403 (3)	C20—H20A	0.9800
C5—H5	0.9500	C20—H20B	0.9800
C6—C7	1.418 (3)	C20—H20C	0.9800

C19—O2—H2	102.3 (19)	H9A—C9—H9B	107.7
H11—O1W—H12	104 (3)	C12—C10—N2	121.26 (17)
C1—N1—C11	107.94 (15)	C12—C10—C11	124.55 (16)
C1—N1—H1	129.4 (16)	N2—C10—C11	114.15 (15)
C11—N1—H1	122.2 (16)	C7—C11—N1	109.94 (17)
C15—N2—C10	122.12 (15)	C7—C11—C10	124.60 (16)
C15—N2—C9	116.72 (15)	N1—C11—C10	125.37 (16)
C10—N2—C9	120.11 (16)	C10—C12—C13	120.54 (16)
C16—N3—C17	116.71 (17)	C10—C12—H12A	119.7
N1—C1—C2	129.66 (17)	C13—C12—H12A	119.7
N1—C1—C6	108.67 (16)	C14—C13—C12	117.92 (16)
C2—C1—C6	121.66 (17)	C14—C13—C18	116.52 (17)
C3—C2—C1	117.27 (17)	C12—C13—C18	125.56 (16)
C3—C2—H2A	121.4	C16—C14—C13	120.08 (16)
C1—C2—H2A	121.4	C16—C14—C15	118.13 (16)
C2—C3—C4	121.95 (17)	C13—C14—C15	121.74 (17)
C2—C3—H3	119.0	O1—C15—N2	120.96 (17)
C4—C3—H3	119.0	O1—C15—C14	122.63 (18)
C5—C4—C3	120.55 (18)	N2—C15—C14	116.38 (16)
C5—C4—H4	119.7	N3—C16—C14	123.12 (16)
C3—C4—H4	119.7	N3—C16—H16	118.4
C4—C5—C6	119.14 (17)	C14—C16—H16	118.4
C4—C5—H5	120.4	N3—C17—C18	125.27 (19)
C6—C5—H5	120.4	N3—C17—H17	117.4
C5—C6—C1	119.41 (17)	C18—C17—H17	117.4
C5—C6—C7	134.32 (17)	C17—C18—C13	118.21 (17)
C1—C6—C7	106.26 (16)	C17—C18—C19	118.98 (17)
C11—C7—C6	107.19 (16)	C13—C18—C19	122.73 (17)
C11—C7—C8	121.06 (17)	O2—C19—C20	108.34 (17)
C6—C7—C8	131.75 (17)	O2—C19—C18	109.32 (16)
C7—C8—C9	108.24 (15)	C20—C19—C18	113.28 (16)
C7—C8—H8A	110.1	O2—C19—H19	108.6
C9—C8—H8A	110.1	C20—C19—H19	108.6
C7—C8—H8B	110.1	C18—C19—H19	108.6
C9—C8—H8B	110.1	C19—C20—H20A	109.5
H8A—C8—H8B	108.4	C19—C20—H20B	109.5
N2—C9—C8	113.37 (16)	H20A—C20—H20B	109.5
N2—C9—H9A	108.9	C19—C20—H20C	109.5
C8—C9—H9A	108.9	H20A—C20—H20C	109.5
N2—C9—H9B	108.9	H20B—C20—H20C	109.5
C8—C9—H9B	108.9

C11—N1—C1—C2	−177.98 (19)	N2—C10—C11—C7	10.4 (3)
C11—N1—C1—C6	0.94 (19)	C12—C10—C11—N1	8.9 (3)
N1—C1—C2—C3	−179.93 (17)	N2—C10—C11—N1	−173.35 (17)
C6—C1—C2—C3	1.3 (3)	N2—C10—C12—C13	1.9 (3)
C1—C2—C3—C4	−1.2 (3)	C11—C10—C12—C13	179.54 (17)
C2—C3—C4—C5	0.3 (3)	C10—C12—C13—C14	−2.7 (3)
C3—C4—C5—C6	0.6 (3)	C10—C12—C13—C18	178.32 (18)
C4—C5—C6—C1	−0.5 (3)	C12—C13—C14—C16	179.44 (17)
C4—C5—C6—C7	−178.7 (2)	C18—C13—C14—C16	−1.5 (3)
N1—C1—C6—C5	−179.48 (16)	C12—C13—C14—C15	2.1 (3)
C2—C1—C6—C5	−0.5 (3)	C18—C13—C14—C15	−178.81 (17)
N1—C1—C6—C7	−0.8 (2)	C10—N2—C15—O1	−178.32 (18)
C2—C1—C6—C7	178.23 (17)	C9—N2—C15—O1	−10.0 (3)
C5—C6—C7—C11	178.7 (2)	C10—N2—C15—C14	−0.1 (3)
C1—C6—C7—C11	0.3 (2)	C9—N2—C15—C14	168.16 (17)
C5—C6—C7—C8	−1.8 (4)	C16—C14—C15—O1	0.0 (3)
C1—C6—C7—C8	179.82 (19)	C13—C14—C15—O1	177.41 (18)
C11—C7—C8—C9	−26.5 (3)	C16—C14—C15—N2	−178.11 (18)
C6—C7—C8—C9	154.1 (2)	C13—C14—C15—N2	−0.7 (3)
C15—N2—C9—C8	147.19 (18)	C17—N3—C16—C14	3.0 (3)
C10—N2—C9—C8	−44.3 (3)	C13—C14—C16—N3	−1.6 (3)
C7—C8—C9—N2	47.4 (2)	C15—C14—C16—N3	175.87 (18)
C15—N2—C10—C12	−0.5 (3)	C16—N3—C17—C18	−1.5 (3)
C9—N2—C10—C12	−168.38 (18)	N3—C17—C18—C13	−1.4 (3)
C15—N2—C10—C11	−178.32 (17)	N3—C17—C18—C19	175.34 (19)
C9—N2—C10—C11	13.8 (2)	C14—C13—C18—C17	2.8 (3)
C6—C7—C11—N1	0.2 (2)	C12—C13—C18—C17	−178.17 (18)
C8—C7—C11—N1	−179.32 (17)	C14—C13—C18—C19	−173.81 (17)
C6—C7—C11—C10	176.94 (17)	C12—C13—C18—C19	5.2 (3)
C8—C7—C11—C10	−2.6 (3)	C17—C18—C19—O2	−41.1 (2)
C1—N1—C11—C7	−0.7 (2)	C13—C18—C19—O2	135.53 (18)
C1—N1—C11—C10	−177.41 (17)	C17—C18—C19—C20	79.8 (2)
C12—C10—C11—C7	−167.33 (19)	C13—C18—C19—C20	−103.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N3ⁱ	0.97 (4)	1.77 (4)	2.732 (2)	171 (3)
O1w—H11···O1ⁱⁱ	0.85 (4)	2.08 (4)	2.928 (2)	169 (3)
O1w—H12···O2ⁱⁱⁱ	0.83 (4)	1.95 (4)	2.762 (2)	167 (3)
N1—H1···O1w	0.85 (3)	2.02 (3)	2.861 (2)	177 (2)

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₇N₃O₂·H₂O
M_r	349.38
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	100
a, b, c (Å)	8.8350 (3), 6.7002 (2), 14.7347 (4)
β (°)	103.117 (3)
V (Å³)	849.48 (4)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	0.76
Crystal size (mm)	0.30 × 0.03 × 0.03

Data collection
Diffractometer	Agilent SuperNova Dual with an Atlas detector diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.803, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	6453, 3252, 3015
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.624

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.098, 1.02
No. of reflections	3252
No. of parameters	251
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.23
Absolute structure	Flack (1983), 1395 Friedel pairs
Absolute structure parameter	0.1 (2)

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N3ⁱ	0.97 (4)	1.77 (4)	2.732 (2)	171 (3)
O1w—H11···O1ⁱⁱ	0.85 (4)	2.08 (4)	2.928 (2)	169 (3)
O1w—H12···O2ⁱⁱⁱ	0.83 (4)	1.95 (4)	2.762 (2)	167 (3)
N1—H1···O1w	0.85 (3)	2.02 (3)	2.861 (2)	177 (2)

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

Acknowledgements

This work was carried under the aegis of a University of Malaya–CNRS (France) collaborative framework. We thank the Ministry of Higher Education (grant No. FRGS-FP016/2010 A) for financial support.

References

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Volume 67| Part 7| July 2011| Pages o1727-o1728

doi:10.1107/S1600536811022768

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

1-(1-Hy­dr­oxy­eth­yl)-7,8-di­hydro­indolo[2,3-a]pyridine­[3,4-g]quinolizin-5(13H)-one (angustoline) monohydrate from Nauclea subdita (Rubiaceae)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1-(1-Hydroxyethyl)-7,8-dihydroindolo[2,3-a]pyridine[3,4-g]quinolizin-5(13H)-one (angustoline) monohydrate from Nauclea subdita (Rubiaceae)