2-(3-Morpholino-prop-yl)-2,3-dihydro-1H-pyrrolo-[3,4-b]quinolin-1-one monohydrate.

In the title compound, C(18)H(21)N(3)O(2)·H(2)O, the fused-ring system is approximately planar [maximum atomic deviation = 0.028 (3) Å]; the morpholine ring displays a chair conformation. The crystal packing is stabilized by classical inter-molecular O-H⋯O and O-H⋯N hydrogen bonds and weak C-H⋯O hydrogen bonds between the organic mol-ecules and the water mol-ecules.

Related literature

For the properties and biological activity of quinoline deriv­atives, see: Vaitilingam et al. (2004 ▶); Lee et al. (2004 ▶); Zwaagstra et al. (1998 ▶); Roma et al. (2000 ▶); Ferrarini et al. (2000 ▶). For the preparation of quinoline derivatives, see: Zhou et al. (2010 ▶); Yang et al. (2008 ▶).

Experimental

Crystal data

C18H21N3O2·H2O

M = 329.39

Orthorhombic,

a = 7.0107 (16) Å

b = 12.655 (3) Å

c = 37.609 (9) Å

V = 3336.7 (13) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.30 × 0.28 × 0.27 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

15458 measured reflections

2943 independent reflections

1864 reflections with I > 2σ(I)

R int = 0.067

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.144

S = 1.04

2943 reflections

225 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.41 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810046349/xu5085sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810046349/xu5085Isup2.hkl

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

C18H21N3O2·H2O	F(000) = 1408.0
Mr = 329.39	Dx = 1.311 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1868 reflections
a = 7.0107 (16) Å	θ = 3.1–20.4°
b = 12.655 (3) Å	µ = 0.09 mm−1
c = 37.609 (9) Å	T = 296 K
V = 3336.7 (13) Å3	Block, colorless
Z = 8	0.30 × 0.28 × 0.27 mm

Bruker SMART 1000 CCD area-detector diffractometer	1864 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.067
graphite	θmax = 25.0°, θmin = 2.2°
φ and ω scans	h = −8→7
15458 measured reflections	k = −15→14
2943 independent reflections	l = −44→41

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0611P)2 + 1.0475P] where P = (Fo2 + 2Fc2)/3
2943 reflections	(Δ/σ)max < 0.001
225 parameters	Δρmax = 0.28 e Å−3
3 restraints	Δρmin = −0.41 e Å−3

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 > 2sigma(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
N1	0.1806 (3)	0.84470 (14)	0.25789 (5)	0.0447 (5)
O1	0.1534 (3)	1.07919 (12)	0.35666 (4)	0.0547 (5)
N2	0.1728 (3)	0.89892 (13)	0.35114 (5)	0.0406 (5)
N3	−0.1048 (3)	0.66704 (14)	0.44146 (5)	0.0431 (5)
O2	−0.2365 (3)	0.47670 (15)	0.47362 (5)	0.0807 (7)
C6	0.1586 (3)	1.02874 (17)	0.23807 (6)	0.0401 (6)
C5	0.1701 (3)	0.91850 (17)	0.23121 (6)	0.0402 (6)
C4	0.1701 (4)	0.8838 (2)	0.19565 (6)	0.0509 (7)
H4	0.1744	0.8119	0.1907	0.061*
C1	0.1522 (4)	1.09912 (19)	0.20898 (7)	0.0519 (7)
H1	0.1446	1.1714	0.2132	0.062*
C3	0.1638 (4)	0.9544 (2)	0.16832 (7)	0.0561 (7)
H3	0.1642	0.9301	0.1450	0.067*
C2	0.1569 (4)	1.0629 (2)	0.17496 (7)	0.0582 (7)
H2	0.1554	1.1104	0.1561	0.070*
C9	0.1791 (3)	0.88333 (16)	0.29006 (6)	0.0386 (6)
C8	0.1644 (3)	0.99006 (16)	0.29942 (5)	0.0371 (6)
C10	0.1624 (3)	0.99828 (17)	0.33838 (6)	0.0399 (6)
C7	0.1545 (3)	1.06426 (17)	0.27334 (6)	0.0416 (6)
H7	0.1454	1.1358	0.2787	0.050*
C11	0.1741 (4)	0.87224 (18)	0.38875 (6)	0.0445 (6)
H11A	0.1305	0.9325	0.4025	0.053*
H11B	0.3034	0.8560	0.3961	0.053*
C13	0.0266 (4)	0.75468 (17)	0.43519 (6)	0.0443 (6)
H13A	0.1507	0.7370	0.4450	0.053*
H13B	−0.0197	0.8171	0.4474	0.053*
C12	0.0472 (4)	0.77880 (18)	0.39619 (6)	0.0454 (6)
H12A	0.0990	0.7172	0.3843	0.054*
H12B	−0.0781	0.7924	0.3863	0.054*
C15	−0.1663 (5)	0.4788 (2)	0.43826 (7)	0.0720 (9)
H15A	−0.2717	0.4900	0.4220	0.086*
H15B	−0.1090	0.4111	0.4327	0.086*
C17	−0.1709 (5)	0.6639 (2)	0.47821 (7)	0.0656 (9)
H17A	−0.2290	0.7310	0.4844	0.079*
H17B	−0.0636	0.6521	0.4940	0.079*
C14	−0.0214 (4)	0.56444 (18)	0.43321 (7)	0.0547 (7)
H14A	0.0871	0.5517	0.4486	0.066*
H14B	0.0234	0.5641	0.4088	0.066*
C16	−0.3143 (5)	0.5764 (2)	0.48256 (9)	0.0875 (12)
H16A	−0.3581	0.5748	0.5070	0.105*
H16B	−0.4237	0.5905	0.4675	0.105*
C18	0.1877 (4)	0.81867 (18)	0.32341 (6)	0.0467 (6)
H18A	0.0826	0.7690	0.3246	0.056*
H18B	0.3072	0.7803	0.3251	0.056*
O1W	0.5672 (4)	0.72672 (19)	0.39612 (10)	0.1179 (11)
H1W	0.638 (6)	0.695 (3)	0.4116 (10)	0.17 (2)*
H2W	0.506 (6)	0.678 (3)	0.3845 (11)	0.20 (2)*

	U11	U22	U33	U12	U13	U23
N1	0.0601 (15)	0.0386 (10)	0.0354 (11)	0.0044 (10)	−0.0005 (9)	0.0000 (8)
O1	0.0741 (14)	0.0385 (9)	0.0515 (10)	−0.0030 (8)	0.0045 (9)	−0.0100 (8)
N2	0.0512 (13)	0.0360 (10)	0.0346 (10)	−0.0028 (9)	0.0013 (9)	−0.0007 (8)
N3	0.0506 (13)	0.0402 (11)	0.0384 (11)	−0.0036 (9)	0.0092 (9)	−0.0022 (8)
O2	0.120 (2)	0.0528 (12)	0.0695 (13)	−0.0217 (12)	0.0372 (13)	−0.0008 (9)
C6	0.0372 (15)	0.0409 (13)	0.0424 (13)	−0.0019 (11)	−0.0023 (11)	0.0071 (10)
C5	0.0361 (14)	0.0451 (14)	0.0393 (13)	0.0026 (11)	−0.0004 (11)	0.0037 (10)
C4	0.0583 (18)	0.0533 (15)	0.0410 (14)	0.0107 (13)	−0.0017 (12)	0.0002 (12)
C1	0.0547 (18)	0.0467 (14)	0.0543 (16)	−0.0010 (12)	−0.0034 (13)	0.0114 (12)
C3	0.0527 (18)	0.0750 (19)	0.0406 (14)	0.0123 (14)	−0.0010 (12)	0.0058 (13)
C2	0.0565 (19)	0.0665 (18)	0.0517 (17)	0.0026 (14)	−0.0005 (14)	0.0192 (13)
C9	0.0429 (15)	0.0352 (12)	0.0378 (13)	0.0001 (10)	0.0004 (11)	0.0005 (10)
C8	0.0382 (14)	0.0332 (12)	0.0400 (13)	−0.0036 (10)	0.0025 (11)	−0.0001 (9)
C10	0.0389 (14)	0.0363 (13)	0.0444 (14)	−0.0037 (10)	0.0019 (11)	−0.0029 (10)
C7	0.0445 (16)	0.0338 (12)	0.0465 (14)	−0.0035 (11)	−0.0017 (12)	−0.0003 (10)
C11	0.0495 (16)	0.0495 (14)	0.0346 (13)	−0.0068 (12)	−0.0018 (11)	0.0005 (10)
C13	0.0513 (16)	0.0429 (13)	0.0387 (13)	−0.0055 (12)	−0.0027 (11)	0.0000 (10)
C12	0.0519 (17)	0.0450 (14)	0.0393 (13)	−0.0069 (12)	−0.0013 (11)	0.0015 (10)
C15	0.096 (3)	0.0501 (16)	0.070 (2)	−0.0123 (16)	0.0266 (18)	−0.0086 (14)
C17	0.091 (2)	0.0552 (16)	0.0503 (16)	−0.0108 (16)	0.0242 (15)	−0.0076 (12)
C14	0.068 (2)	0.0441 (14)	0.0522 (15)	0.0011 (13)	0.0158 (14)	0.0000 (11)
C16	0.114 (3)	0.062 (2)	0.086 (2)	−0.0226 (19)	0.054 (2)	−0.0117 (16)
C18	0.0626 (18)	0.0372 (13)	0.0402 (13)	−0.0027 (12)	0.0009 (12)	−0.0006 (10)
O1W	0.091 (2)	0.0689 (15)	0.194 (3)	0.0150 (14)	−0.066 (2)	−0.0318 (18)

N1—C9	1.305 (3)	C8—C10	1.469 (3)
N1—C5	1.373 (3)	C7—H7	0.9300
O1—C10	1.235 (3)	C11—C12	1.506 (3)
N2—C10	1.348 (3)	C11—H11A	0.9700
N2—C11	1.454 (3)	C11—H11B	0.9700
N2—C18	1.460 (3)	C13—C12	1.505 (3)
N3—C14	1.458 (3)	C13—H13A	0.9700
N3—C17	1.458 (3)	C13—H13B	0.9700
N3—C13	1.461 (3)	C12—H12A	0.9700
O2—C15	1.418 (3)	C12—H12B	0.9700
O2—C16	1.415 (4)	C15—C14	1.498 (4)
C6—C7	1.401 (3)	C15—H15A	0.9700
C6—C1	1.411 (3)	C15—H15B	0.9700
C6—C5	1.421 (3)	C17—C16	1.505 (4)
C5—C4	1.408 (3)	C17—H17A	0.9700
C4—C3	1.362 (3)	C17—H17B	0.9700
C4—H4	0.9300	C14—H14A	0.9700
C1—C2	1.360 (3)	C14—H14B	0.9700
C1—H1	0.9300	C16—H16A	0.9700
C3—C2	1.397 (4)	C16—H16B	0.9700
C3—H3	0.9300	C18—H18A	0.9700
C2—H2	0.9300	C18—H18B	0.9700
C9—C8	1.400 (3)	O1W—H1W	0.86 (4)
C9—C18	1.499 (3)	O1W—H2W	0.87 (4)
C8—C7	1.360 (3)
C9—N1—C5	114.99 (18)	N3—C13—C12	111.82 (18)
C10—N2—C11	124.29 (19)	N3—C13—H13A	109.3
C10—N2—C18	113.48 (18)	C12—C13—H13A	109.3
C11—N2—C18	122.21 (17)	N3—C13—H13B	109.3
C14—N3—C17	107.80 (19)	C12—C13—H13B	109.3
C14—N3—C13	112.86 (19)	H13A—C13—H13B	107.9
C17—N3—C13	111.95 (18)	C11—C12—C13	113.39 (19)
C15—O2—C16	109.9 (2)	C11—C12—H12A	108.9
C7—C6—C1	122.1 (2)	C13—C12—H12A	108.9
C7—C6—C5	119.21 (19)	C11—C12—H12B	108.9
C1—C6—C5	118.7 (2)	C13—C12—H12B	108.9
N1—C5—C4	118.8 (2)	H12A—C12—H12B	107.7
N1—C5—C6	122.6 (2)	O2—C15—C14	111.6 (2)
C4—C5—C6	118.6 (2)	O2—C15—H15A	109.3
C3—C4—C5	120.8 (2)	C14—C15—H15A	109.3
C3—C4—H4	119.6	O2—C15—H15B	109.3
C5—C4—H4	119.6	C14—C15—H15B	109.3
C2—C1—C6	121.1 (2)	H15A—C15—H15B	108.0
C2—C1—H1	119.5	N3—C17—C16	109.6 (2)
C6—C1—H1	119.5	N3—C17—H17A	109.8
C4—C3—C2	120.7 (2)	C16—C17—H17A	109.8
C4—C3—H3	119.6	N3—C17—H17B	109.8
C2—C3—H3	119.6	C16—C17—H17B	109.8
C1—C2—C3	120.0 (2)	H17A—C17—H17B	108.2
C1—C2—H2	120.0	N3—C14—C15	110.2 (2)
C3—C2—H2	120.0	N3—C14—H14A	109.6
N1—C9—C8	126.5 (2)	C15—C14—H14A	109.6
N1—C9—C18	124.83 (19)	N3—C14—H14B	109.6
C8—C9—C18	108.63 (18)	C15—C14—H14B	109.6
C7—C8—C9	119.3 (2)	H14A—C14—H14B	108.1
C7—C8—C10	132.08 (19)	O2—C16—C17	111.9 (3)
C9—C8—C10	108.65 (18)	O2—C16—H16A	109.2
O1—C10—N2	125.3 (2)	C17—C16—H16A	109.2
O1—C10—C8	127.9 (2)	O2—C16—H16B	109.2
N2—C10—C8	106.78 (18)	C17—C16—H16B	109.2
C8—C7—C6	117.4 (2)	H16A—C16—H16B	107.9
C8—C7—H7	121.3	N2—C18—C9	102.43 (17)
C6—C7—H7	121.3	N2—C18—H18A	111.3
N2—C11—C12	111.07 (18)	C9—C18—H18A	111.3
N2—C11—H11A	109.4	N2—C18—H18B	111.3
C12—C11—H11A	109.4	C9—C18—H18B	111.3
N2—C11—H11B	109.4	H18A—C18—H18B	109.2
C12—C11—H11B	109.4	H1W—O1W—H2W	107 (4)
H11A—C11—H11B	108.0
C9—N1—C5—C4	−179.8 (2)	C7—C8—C10—N2	179.0 (3)
C9—N1—C5—C6	0.1 (3)	C9—C8—C10—N2	−0.9 (3)
C7—C6—C5—N1	−1.1 (4)	C9—C8—C7—C6	0.4 (3)
C1—C6—C5—N1	178.7 (2)	C10—C8—C7—C6	−179.5 (2)
C7—C6—C5—C4	178.7 (2)	C1—C6—C7—C8	−179.0 (2)
C1—C6—C5—C4	−1.4 (3)	C5—C6—C7—C8	0.8 (3)
N1—C5—C4—C3	−178.7 (2)	C10—N2—C11—C12	137.0 (2)
C6—C5—C4—C3	1.5 (4)	C18—N2—C11—C12	−44.5 (3)
C7—C6—C1—C2	179.8 (2)	C14—N3—C13—C12	75.8 (3)
C5—C6—C1—C2	0.0 (4)	C17—N3—C13—C12	−162.4 (2)
C5—C4—C3—C2	−0.1 (4)	N2—C11—C12—C13	−173.9 (2)
C6—C1—C2—C3	1.5 (4)	N3—C13—C12—C11	177.1 (2)
C4—C3—C2—C1	−1.4 (4)	C16—O2—C15—C14	56.8 (4)
C5—N1—C9—C8	1.3 (4)	C14—N3—C17—C16	−58.6 (3)
C5—N1—C9—C18	179.5 (2)	C13—N3—C17—C16	176.7 (2)
N1—C9—C8—C7	−1.6 (4)	C17—N3—C14—C15	59.0 (3)
C18—C9—C8—C7	180.0 (2)	C13—N3—C14—C15	−176.9 (2)
N1—C9—C8—C10	178.3 (2)	O2—C15—C14—N3	−59.0 (3)
C18—C9—C8—C10	−0.2 (3)	C15—O2—C16—C17	−57.1 (4)
C11—N2—C10—O1	0.3 (4)	N3—C17—C16—O2	59.1 (4)
C18—N2—C10—O1	−178.3 (2)	C10—N2—C18—C9	−1.7 (3)
C11—N2—C10—C8	−179.8 (2)	C11—N2—C18—C9	179.7 (2)
C18—N2—C10—C8	1.6 (3)	N1—C9—C18—N2	−177.5 (2)
C7—C8—C10—O1	−1.1 (5)	C8—C9—C18—N2	1.0 (3)
C9—C8—C10—O1	179.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···N3i	0.86 (4)	2.15 (4)	2.961 (4)	155 (4)
O1W—H2W···O1ii	0.87 (4)	1.98 (4)	2.843 (3)	174 (4)
C11—H11B···O1W	0.97	2.47	3.326 (4)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯N3i	0.86 (4)	2.15 (4)	2.961 (4)	155 (4)
O1W—H2W⋯O1ii	0.87 (4)	1.98 (4)	2.843 (3)	174 (4)
C11—H11B⋯O1W	0.97	2.47	3.326 (4)	147

Symmetry codes: (i) ; (ii) .