3-(7-Meth-oxy-β-carbolin-1-yl)propionic acid monohydrate.

In the title compound, C(15)H(14)N(2)O(3)·H(2)O [systematic name: 3-(7-meth-oxy-9H-pyrido[3,4-b]indol-1-yl)propanoic acid monohydrate], the fused rings make dhedral angles of 0.4 (1), 1.1 (2) and 1.4 (2)°. In the crystal, the water mol-ecule is involved in the formation of three independent hydrogen-bonded chains via O-H⋯O and N-H⋯O hydrogen bonds, while the carb-oxy group forms an inter-molecular O-H⋯N hydrogen bond.

Related literature

For the isolation of the title compound, see: Kardono et al. (1991 ▶). For the preparation, see: Kardono et al. (1991 ▶). For its pharmacological activity, see: Kuo et al. (2003 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H14N2O3·H2O

M = 288.30

Monoclinic,

a = 4.5114 (1) Å

b = 10.8637 (2) Å

c = 28.0865 (3) Å

β = 92.414 (1)°

V = 1375.31 (4) Å3

Z = 4

Cu Kα radiation

μ = 0.85 mm−1

T = 296 K

0.12 × 0.10 × 0.05 mm

Data collection

Bruker APEXII diffractometer

9119 measured reflections

2366 independent reflections

2048 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.116

S = 1.05

2366 reflections

201 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.49 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681101350X/mw2003sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681101350X/mw2003Isup2.hkl

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

C15H14N2O3·H2O	F(000) = 608
Mr = 288.30	Dx = 1.392 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2yn	Cell parameters from 3368 reflections
a = 4.5114 (1) Å	θ = 3.2–67.6°
b = 10.8637 (2) Å	µ = 0.85 mm−1
c = 28.0865 (3) Å	T = 296 K
β = 92.414 (1)°	Prism, colourless
V = 1375.31 (4) Å3	0.12 × 0.10 × 0.05 mm
Z = 4

Bruker APEXII diffractometer	2048 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.022
graphite	θmax = 67.6°, θmin = 3.2°
Detector resolution: 0 pixels mm-1	h = −4→5
φ and ω scans	k = −12→12
9119 measured reflections	l = −33→33
2366 independent reflections

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)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.116	w = 1/[σ2(Fo2) + (0.0672P)2 + 0.3134P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.006
2366 reflections	Δρmax = 0.49 e Å−3
201 parameters	Δρmin = −0.17 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0014 (3)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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.

	x	y	z	Uiso*/Ueq
C1	0.0343 (3)	0.45008 (14)	0.16867 (5)	0.0351 (3)
N2	0.0495 (3)	0.32718 (11)	0.16361 (5)	0.0402 (3)
C3	0.2158 (4)	0.27148 (15)	0.13080 (6)	0.0458 (4)
H3A	0.2177	0.1860	0.1291	0.055*
C4	0.3807 (4)	0.33780 (15)	0.10014 (6)	0.0438 (4)
H4A	0.4925	0.2985	0.0776	0.053*
C5	0.7128 (4)	0.57535 (16)	0.04262 (6)	0.0443 (4)
H5A	0.7804	0.5050	0.0276	0.053*
C6	0.8037 (4)	0.68936 (17)	0.02872 (6)	0.0487 (4)
H6A	0.9324	0.6962	0.0039	0.058*
C7	0.7055 (4)	0.79694 (16)	0.05145 (6)	0.0460 (4)
C8	0.5138 (4)	0.79159 (15)	0.08833 (6)	0.0427 (4)
H8A	0.4502	0.8624	0.1035	0.051*
C9	0.4200 (3)	0.67511 (14)	0.10178 (5)	0.0374 (4)
C10	0.5163 (3)	0.56590 (14)	0.07978 (5)	0.0381 (4)
C11	0.3771 (3)	0.46622 (14)	0.10355 (5)	0.0370 (3)
C12	0.2008 (3)	0.52071 (14)	0.13862 (5)	0.0350 (3)
N13	0.2299 (3)	0.64599 (12)	0.13699 (4)	0.0381 (3)
H13A	0.1437	0.6978	0.1550	0.046*
O14	0.8192 (3)	0.90335 (12)	0.03401 (5)	0.0602 (4)
C15	0.7305 (6)	1.01607 (19)	0.05520 (8)	0.0734 (7)
H15A	0.8250	1.0837	0.0399	0.110*
H15B	0.7877	1.0156	0.0885	0.110*
H15C	0.5191	1.0248	0.0514	0.110*
C1'	−0.1536 (3)	0.50276 (13)	0.20627 (5)	0.0364 (4)
H1'A	−0.3104	0.4449	0.2129	0.044*
H1'B	−0.2458	0.5780	0.1944	0.044*
C2'	0.0251 (4)	0.53087 (15)	0.25274 (6)	0.0437 (4)
H2'A	0.0966	0.4545	0.2670	0.052*
H2'B	0.1957	0.5811	0.2458	0.052*
C3'	−0.1657 (4)	0.59823 (14)	0.28756 (5)	0.0416 (4)
O4'	−0.2512 (4)	0.54636 (12)	0.32330 (4)	0.0655 (4)
O5'	−0.2315 (4)	0.70783 (11)	0.27682 (5)	0.0618 (4)
H5'A	−0.3268	0.7384	0.2981	0.25 (3)*
OW	0.9592 (4)	0.81052 (13)	0.19395 (6)	0.0690 (5)
HWA	0.894 (5)	0.789 (2)	0.2205 (10)	0.081 (8)*
HWB	0.882 (5)	0.883 (3)	0.1889 (9)	0.076 (7)*

	U11	U22	U33	U12	U13	U23
C1	0.0370 (8)	0.0361 (8)	0.0322 (7)	−0.0001 (6)	0.0022 (6)	−0.0003 (6)
N2	0.0474 (8)	0.0356 (7)	0.0381 (7)	0.0008 (5)	0.0062 (6)	−0.0012 (5)
C3	0.0572 (10)	0.0358 (8)	0.0450 (9)	0.0031 (7)	0.0082 (7)	−0.0047 (6)
C4	0.0489 (9)	0.0433 (9)	0.0397 (8)	0.0070 (7)	0.0089 (7)	−0.0061 (6)
C5	0.0431 (9)	0.0531 (10)	0.0374 (8)	0.0014 (7)	0.0097 (7)	−0.0048 (7)
C6	0.0482 (10)	0.0627 (11)	0.0363 (8)	−0.0041 (8)	0.0146 (7)	0.0008 (7)
C7	0.0487 (9)	0.0521 (10)	0.0375 (8)	−0.0068 (7)	0.0064 (7)	0.0072 (7)
C8	0.0483 (9)	0.0419 (9)	0.0383 (8)	−0.0002 (7)	0.0084 (7)	0.0012 (6)
C9	0.0384 (8)	0.0422 (8)	0.0318 (7)	0.0006 (6)	0.0049 (6)	0.0006 (6)
C10	0.0376 (8)	0.0443 (9)	0.0326 (7)	0.0012 (6)	0.0039 (6)	−0.0012 (6)
C11	0.0371 (8)	0.0411 (8)	0.0330 (7)	0.0028 (6)	0.0029 (6)	−0.0026 (6)
C12	0.0362 (8)	0.0372 (8)	0.0316 (7)	0.0019 (6)	0.0033 (6)	−0.0009 (6)
N13	0.0440 (7)	0.0350 (7)	0.0362 (6)	0.0021 (5)	0.0120 (5)	−0.0008 (5)
O14	0.0749 (9)	0.0543 (8)	0.0530 (7)	−0.0113 (6)	0.0232 (6)	0.0087 (6)
C15	0.1093 (18)	0.0520 (12)	0.0610 (12)	−0.0196 (11)	0.0274 (12)	0.0019 (9)
C1'	0.0378 (8)	0.0352 (8)	0.0367 (8)	−0.0002 (6)	0.0081 (6)	0.0004 (6)
C2'	0.0472 (9)	0.0451 (9)	0.0389 (8)	0.0062 (7)	0.0038 (7)	−0.0023 (7)
C3'	0.0501 (9)	0.0387 (8)	0.0365 (8)	−0.0028 (6)	0.0061 (7)	−0.0041 (6)
O4'	0.1062 (11)	0.0451 (7)	0.0477 (7)	−0.0034 (7)	0.0302 (7)	−0.0001 (5)
O5'	0.0916 (10)	0.0433 (7)	0.0528 (8)	0.0155 (6)	0.0297 (7)	0.0040 (5)
OW	0.1082 (13)	0.0425 (7)	0.0594 (9)	0.0149 (7)	0.0382 (8)	0.0023 (6)

C1—N2	1.3447 (19)	C10—C11	1.431 (2)
C1—C12	1.385 (2)	C11—C12	1.421 (2)
C1—C1'	1.4955 (19)	C12—N13	1.3683 (19)
N2—C3	1.355 (2)	N13—H13A	0.8600
C3—C4	1.367 (2)	O14—C15	1.426 (2)
C3—H3A	0.9300	C15—H15A	0.9600
C4—C11	1.399 (2)	C15—H15B	0.9600
C4—H4A	0.9300	C15—H15C	0.9600
C5—C6	1.367 (2)	C1'—C2'	1.535 (2)
C5—C10	1.401 (2)	C1'—H1'A	0.9700
C5—H5A	0.9300	C1'—H1'B	0.9700
C6—C7	1.412 (2)	C2'—C3'	1.518 (2)
C6—H6A	0.9300	C2'—H2'A	0.9700
C7—O14	1.364 (2)	C2'—H2'B	0.9700
C7—C8	1.378 (2)	C3'—O4'	1.228 (2)
C8—C9	1.392 (2)	C3'—O5'	1.261 (2)
C8—H8A	0.9300	O5'—H5'A	0.8200
C9—N13	1.3728 (19)	OW—HWA	0.85 (3)
C9—C10	1.414 (2)	OW—HWB	0.87 (3)
N2—C1—C12	117.01 (13)	N13—C12—C1	128.81 (13)
N2—C1—C1'	119.18 (13)	N13—C12—C11	109.50 (13)
C12—C1—C1'	123.80 (13)	C1—C12—C11	121.69 (14)
C1—N2—C3	123.20 (13)	C12—N13—C9	108.49 (12)
N2—C3—C4	121.64 (15)	C12—N13—H13A	125.8
N2—C3—H3A	119.2	C9—N13—H13A	125.8
C4—C3—H3A	119.2	C7—O14—C15	117.49 (14)
C3—C4—C11	118.33 (14)	O14—C15—H15A	109.5
C3—C4—H4A	120.8	O14—C15—H15B	109.5
C11—C4—H4A	120.8	H15A—C15—H15B	109.5
C6—C5—C10	119.07 (15)	O14—C15—H15C	109.5
C6—C5—H5A	120.5	H15A—C15—H15C	109.5
C10—C5—H5A	120.5	H15B—C15—H15C	109.5
C5—C6—C7	121.16 (15)	C1—C1'—C2'	112.56 (12)
C5—C6—H6A	119.4	C1—C1'—H1'A	109.1
C7—C6—H6A	119.4	C2'—C1'—H1'A	109.1
O14—C7—C8	124.26 (16)	C1—C1'—H1'B	109.1
O14—C7—C6	114.16 (15)	C2'—C1'—H1'B	109.1
C8—C7—C6	121.58 (15)	H1'A—C1'—H1'B	107.8
C7—C8—C9	116.74 (15)	C3'—C2'—C1'	110.62 (13)
C7—C8—H8A	121.6	C3'—C2'—H2'A	109.5
C9—C8—H8A	121.6	C1'—C2'—H2'A	109.5
N13—C9—C8	127.69 (14)	C3'—C2'—H2'B	109.5
N13—C9—C10	109.52 (13)	C1'—C2'—H2'B	109.5
C8—C9—C10	122.79 (14)	H2'A—C2'—H2'B	108.1
C5—C10—C9	118.65 (14)	O4'—C3'—O5'	123.37 (15)
C5—C10—C11	134.97 (15)	O4'—C3'—C2'	120.80 (15)
C9—C10—C11	106.38 (13)	O5'—C3'—C2'	115.82 (14)
C4—C11—C12	118.13 (14)	C3'—O5'—H5'A	109.5
C4—C11—C10	135.75 (14)	HWA—OW—HWB	104 (2)
C12—C11—C10	106.11 (13)
C12—C1—N2—C3	−0.5 (2)	C5—C10—C11—C12	−179.98 (18)
C1'—C1—N2—C3	−179.45 (15)	C9—C10—C11—C12	0.48 (17)
C1—N2—C3—C4	−0.2 (3)	N2—C1—C12—N13	−178.44 (14)
N2—C3—C4—C11	0.6 (3)	C1'—C1—C12—N13	0.4 (2)
C10—C5—C6—C7	0.6 (3)	N2—C1—C12—C11	0.8 (2)
C5—C6—C7—O14	179.06 (15)	C1'—C1—C12—C11	179.69 (14)
C5—C6—C7—C8	−0.3 (3)	C4—C11—C12—N13	178.96 (13)
O14—C7—C8—C9	−179.74 (15)	C10—C11—C12—N13	−0.36 (17)
C6—C7—C8—C9	−0.5 (3)	C4—C11—C12—C1	−0.4 (2)
C7—C8—C9—N13	−179.63 (16)	C10—C11—C12—C1	−179.75 (14)
C7—C8—C9—C10	0.9 (2)	C1—C12—N13—C9	179.43 (15)
C6—C5—C10—C9	−0.3 (2)	C11—C12—N13—C9	0.09 (17)
C6—C5—C10—C11	−179.79 (17)	C8—C9—N13—C12	−179.34 (16)
N13—C9—C10—C5	179.93 (14)	C10—C9—N13—C12	0.22 (17)
C8—C9—C10—C5	−0.5 (2)	C8—C7—O14—C15	−0.7 (3)
N13—C9—C10—C11	−0.44 (17)	C6—C7—O14—C15	−179.95 (18)
C8—C9—C10—C11	179.14 (15)	N2—C1—C1'—C2'	95.18 (16)
C3—C4—C11—C12	−0.3 (2)	C12—C1—C1'—C2'	−83.68 (18)
C3—C4—C11—C10	178.79 (18)	C1—C1'—C2'—C3'	173.08 (13)
C5—C10—C11—C4	0.9 (3)	C1'—C2'—C3'—O4'	108.25 (18)
C9—C10—C11—C4	−178.66 (18)	C1'—C2'—C3'—O5'	−70.68 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N13—H13A···OWi	0.86	1.86	2.7224 (18)	180
O5'—H5'A···N2ii	0.82	1.79	2.5965 (18)	169
OW—HWA···O5'iii	0.85 (3)	1.92 (3)	2.7514 (19)	169 (2)
OW—HWB···O4'iv	0.87 (3)	1.89 (3)	2.764 (2)	175 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N13—H13A⋯OWi	0.86	1.86	2.7224 (18)	180
O5′—H5′A⋯N2ii	0.82	1.79	2.5965 (18)	169
OW—HWA⋯O5′iii	0.85 (3)	1.92 (3)	2.7514 (19)	169 (2)
OW—HWB⋯O4′iv	0.87 (3)	1.89 (3)	2.764 (2)	175 (2)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .