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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): o3180.
Published online 2010 November 13. doi:  10.1107/S1600536810046349
PMCID: PMC3011724

2-(3-Morpholino­prop­yl)-2,3-dihydro-1H-pyrrolo­[3,4-b]quinolin-1-one monohydrate

Abstract

In the title compound, C18H21N3O2·H2O, 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 inter­molecular O—H(...)O and O—H(...)N hydrogen bonds and weak C—H(...)O hydrogen bonds between the organic mol­ecules and the water mol­ecules.

Related literature

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

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Object name is e-66-o3180-scheme1.jpg

Experimental

Crystal data

  • C18H21N3O2·H2O
  • M r = 329.39
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3180-efi1.jpg
  • 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 [triangle]); cell refinement: SAINT (Siemens, 1996 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Acknowledgments

We are grateful to the National Natural Science Foundation of China (grant No. 20802021) and the Natural Science Foundation of Guangdong Province, China (grant No. 8251063101000002).

supplementary crystallographic information

Comment

Quinoline analogues have been reported to display promising antibacterial (Vaitilingam et al., 2004), an-ticancer and antiplatelet (Lee et al., 2004), antiasthmatic (Zwaagstra et al., 1998), antiinflammatory (Roma et al., 2000), and antihypertensive activities (Ferrarini et al., 2000). We have synthesized some new quinoline derivatives (Yang et al., 2008). In continuation of our efforts to develop quinoline derivatives with a new structure-activity relationship, herein, we report the synthesis and structure determination the title compound.

The molecular geometry and the atom-labeling scheme of the title compound is illustrated in Fig. 1. The molecule contains three approximately coplanar rings and the dihedral angle between the three rings 1.60 (2)° and 1.20 (5)°, respectively; the C—N2—C—C torsion angles are 43.59° and -137.51°; the morpholine ring shows a stable chair conformation. The crystal structure can be depicted as layers along a-axis which ring systems are parallel to one another. The crystal packing is stabilized by intermolecular interactions between O and H atoms [C—H···O = 2.638Å].

Experimental

The precursor, ethyl 2-(bromomethyl)quinoline-3-carboxylate, was prepared according to the literature procedure (Yang et al., 2008; Zhou et al., 2010). The title compoud was synthesized by treating 1 mmol of ethyl 2-(bromomethyl)quinoline-3-carboxylate with 1.2 mmol of 3-morpholinopropan-1-amine in the presence of NaHCO3 in acetonitrile. The reaction was carried out under the stirring at room temperature for 10 h. Once the reaction was complete, the solid salt was filtered off and the filtrate was then concentrated under reduced pressure. The crude product was purified by silica gel column chromatography with the mixture of methanol and ethyl acetate (v /v = 1/20) to afford the white product. Crystals suitable for X-ray analysis were obtained by slow evaporation of the solution of petroleum ether and dichloromethane, in which the small amount of water was not removed.

Refinement

Water H atoms were located in a difference Fourier map and refined isotropically. Other H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.93–0.97 Å and Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
Molecular structure of the title compound showing atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
Packing diagram of the title compound.
Fig. 3.
Reaction scheme for the title compound.

Crystal data

C18H21N3O2·H2OF(000) = 1408.0
Mr = 329.39Dx = 1.311 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 1868 reflections
a = 7.0107 (16) Åθ = 3.1–20.4°
b = 12.655 (3) ŵ = 0.09 mm1
c = 37.609 (9) ÅT = 296 K
V = 3336.7 (13) Å3Block, colorless
Z = 80.30 × 0.28 × 0.27 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer1864 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.067
graphiteθmax = 25.0°, θmin = 2.2°
[var phi] and ω scansh = −8→7
15458 measured reflectionsk = −15→14
2943 independent reflectionsl = −44→41

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144H atoms treated by a mixture of independent and constrained refinement
S = 1.04w = 1/[σ2(Fo2) + (0.0611P)2 + 1.0475P] where P = (Fo2 + 2Fc2)/3
2943 reflections(Δ/σ)max < 0.001
225 parametersΔρmax = 0.28 e Å3
3 restraintsΔρmin = −0.41 e Å3

Special details

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.

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

xyzUiso*/Ueq
N10.1806 (3)0.84470 (14)0.25789 (5)0.0447 (5)
O10.1534 (3)1.07919 (12)0.35666 (4)0.0547 (5)
N20.1728 (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)
C60.1586 (3)1.02874 (17)0.23807 (6)0.0401 (6)
C50.1701 (3)0.91850 (17)0.23121 (6)0.0402 (6)
C40.1701 (4)0.8838 (2)0.19565 (6)0.0509 (7)
H40.17440.81190.19070.061*
C10.1522 (4)1.09912 (19)0.20898 (7)0.0519 (7)
H10.14461.17140.21320.062*
C30.1638 (4)0.9544 (2)0.16832 (7)0.0561 (7)
H30.16420.93010.14500.067*
C20.1569 (4)1.0629 (2)0.17496 (7)0.0582 (7)
H20.15541.11040.15610.070*
C90.1791 (3)0.88333 (16)0.29006 (6)0.0386 (6)
C80.1644 (3)0.99006 (16)0.29942 (5)0.0371 (6)
C100.1624 (3)0.99828 (17)0.33838 (6)0.0399 (6)
C70.1545 (3)1.06426 (17)0.27334 (6)0.0416 (6)
H70.14541.13580.27870.050*
C110.1741 (4)0.87224 (18)0.38875 (6)0.0445 (6)
H11A0.13050.93250.40250.053*
H11B0.30340.85600.39610.053*
C130.0266 (4)0.75468 (17)0.43519 (6)0.0443 (6)
H13A0.15070.73700.44500.053*
H13B−0.01970.81710.44740.053*
C120.0472 (4)0.77880 (18)0.39619 (6)0.0454 (6)
H12A0.09900.71720.38430.054*
H12B−0.07810.79240.38630.054*
C15−0.1663 (5)0.4788 (2)0.43826 (7)0.0720 (9)
H15A−0.27170.49000.42200.086*
H15B−0.10900.41110.43270.086*
C17−0.1709 (5)0.6639 (2)0.47821 (7)0.0656 (9)
H17A−0.22900.73100.48440.079*
H17B−0.06360.65210.49400.079*
C14−0.0214 (4)0.56444 (18)0.43321 (7)0.0547 (7)
H14A0.08710.55170.44860.066*
H14B0.02340.56410.40880.066*
C16−0.3143 (5)0.5764 (2)0.48256 (9)0.0875 (12)
H16A−0.35810.57480.50700.105*
H16B−0.42370.59050.46750.105*
C180.1877 (4)0.81867 (18)0.32341 (6)0.0467 (6)
H18A0.08260.76900.32460.056*
H18B0.30720.78030.32510.056*
O1W0.5672 (4)0.72672 (19)0.39612 (10)0.1179 (11)
H1W0.638 (6)0.695 (3)0.4116 (10)0.17 (2)*
H2W0.506 (6)0.678 (3)0.3845 (11)0.20 (2)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0601 (15)0.0386 (10)0.0354 (11)0.0044 (10)−0.0005 (9)0.0000 (8)
O10.0741 (14)0.0385 (9)0.0515 (10)−0.0030 (8)0.0045 (9)−0.0100 (8)
N20.0512 (13)0.0360 (10)0.0346 (10)−0.0028 (9)0.0013 (9)−0.0007 (8)
N30.0506 (13)0.0402 (11)0.0384 (11)−0.0036 (9)0.0092 (9)−0.0022 (8)
O20.120 (2)0.0528 (12)0.0695 (13)−0.0217 (12)0.0372 (13)−0.0008 (9)
C60.0372 (15)0.0409 (13)0.0424 (13)−0.0019 (11)−0.0023 (11)0.0071 (10)
C50.0361 (14)0.0451 (14)0.0393 (13)0.0026 (11)−0.0004 (11)0.0037 (10)
C40.0583 (18)0.0533 (15)0.0410 (14)0.0107 (13)−0.0017 (12)0.0002 (12)
C10.0547 (18)0.0467 (14)0.0543 (16)−0.0010 (12)−0.0034 (13)0.0114 (12)
C30.0527 (18)0.0750 (19)0.0406 (14)0.0123 (14)−0.0010 (12)0.0058 (13)
C20.0565 (19)0.0665 (18)0.0517 (17)0.0026 (14)−0.0005 (14)0.0192 (13)
C90.0429 (15)0.0352 (12)0.0378 (13)0.0001 (10)0.0004 (11)0.0005 (10)
C80.0382 (14)0.0332 (12)0.0400 (13)−0.0036 (10)0.0025 (11)−0.0001 (9)
C100.0389 (14)0.0363 (13)0.0444 (14)−0.0037 (10)0.0019 (11)−0.0029 (10)
C70.0445 (16)0.0338 (12)0.0465 (14)−0.0035 (11)−0.0017 (12)−0.0003 (10)
C110.0495 (16)0.0495 (14)0.0346 (13)−0.0068 (12)−0.0018 (11)0.0005 (10)
C130.0513 (16)0.0429 (13)0.0387 (13)−0.0055 (12)−0.0027 (11)0.0000 (10)
C120.0519 (17)0.0450 (14)0.0393 (13)−0.0069 (12)−0.0013 (11)0.0015 (10)
C150.096 (3)0.0501 (16)0.070 (2)−0.0123 (16)0.0266 (18)−0.0086 (14)
C170.091 (2)0.0552 (16)0.0503 (16)−0.0108 (16)0.0242 (15)−0.0076 (12)
C140.068 (2)0.0441 (14)0.0522 (15)0.0011 (13)0.0158 (14)0.0000 (11)
C160.114 (3)0.062 (2)0.086 (2)−0.0226 (19)0.054 (2)−0.0117 (16)
C180.0626 (18)0.0372 (13)0.0402 (13)−0.0027 (12)0.0009 (12)−0.0006 (10)
O1W0.091 (2)0.0689 (15)0.194 (3)0.0150 (14)−0.066 (2)−0.0318 (18)

Geometric parameters (Å, °)

N1—C91.305 (3)C8—C101.469 (3)
N1—C51.373 (3)C7—H70.9300
O1—C101.235 (3)C11—C121.506 (3)
N2—C101.348 (3)C11—H11A0.9700
N2—C111.454 (3)C11—H11B0.9700
N2—C181.460 (3)C13—C121.505 (3)
N3—C141.458 (3)C13—H13A0.9700
N3—C171.458 (3)C13—H13B0.9700
N3—C131.461 (3)C12—H12A0.9700
O2—C151.418 (3)C12—H12B0.9700
O2—C161.415 (4)C15—C141.498 (4)
C6—C71.401 (3)C15—H15A0.9700
C6—C11.411 (3)C15—H15B0.9700
C6—C51.421 (3)C17—C161.505 (4)
C5—C41.408 (3)C17—H17A0.9700
C4—C31.362 (3)C17—H17B0.9700
C4—H40.9300C14—H14A0.9700
C1—C21.360 (3)C14—H14B0.9700
C1—H10.9300C16—H16A0.9700
C3—C21.397 (4)C16—H16B0.9700
C3—H30.9300C18—H18A0.9700
C2—H20.9300C18—H18B0.9700
C9—C81.400 (3)O1W—H1W0.86 (4)
C9—C181.499 (3)O1W—H2W0.87 (4)
C8—C71.360 (3)
C9—N1—C5114.99 (18)N3—C13—C12111.82 (18)
C10—N2—C11124.29 (19)N3—C13—H13A109.3
C10—N2—C18113.48 (18)C12—C13—H13A109.3
C11—N2—C18122.21 (17)N3—C13—H13B109.3
C14—N3—C17107.80 (19)C12—C13—H13B109.3
C14—N3—C13112.86 (19)H13A—C13—H13B107.9
C17—N3—C13111.95 (18)C11—C12—C13113.39 (19)
C15—O2—C16109.9 (2)C11—C12—H12A108.9
C7—C6—C1122.1 (2)C13—C12—H12A108.9
C7—C6—C5119.21 (19)C11—C12—H12B108.9
C1—C6—C5118.7 (2)C13—C12—H12B108.9
N1—C5—C4118.8 (2)H12A—C12—H12B107.7
N1—C5—C6122.6 (2)O2—C15—C14111.6 (2)
C4—C5—C6118.6 (2)O2—C15—H15A109.3
C3—C4—C5120.8 (2)C14—C15—H15A109.3
C3—C4—H4119.6O2—C15—H15B109.3
C5—C4—H4119.6C14—C15—H15B109.3
C2—C1—C6121.1 (2)H15A—C15—H15B108.0
C2—C1—H1119.5N3—C17—C16109.6 (2)
C6—C1—H1119.5N3—C17—H17A109.8
C4—C3—C2120.7 (2)C16—C17—H17A109.8
C4—C3—H3119.6N3—C17—H17B109.8
C2—C3—H3119.6C16—C17—H17B109.8
C1—C2—C3120.0 (2)H17A—C17—H17B108.2
C1—C2—H2120.0N3—C14—C15110.2 (2)
C3—C2—H2120.0N3—C14—H14A109.6
N1—C9—C8126.5 (2)C15—C14—H14A109.6
N1—C9—C18124.83 (19)N3—C14—H14B109.6
C8—C9—C18108.63 (18)C15—C14—H14B109.6
C7—C8—C9119.3 (2)H14A—C14—H14B108.1
C7—C8—C10132.08 (19)O2—C16—C17111.9 (3)
C9—C8—C10108.65 (18)O2—C16—H16A109.2
O1—C10—N2125.3 (2)C17—C16—H16A109.2
O1—C10—C8127.9 (2)O2—C16—H16B109.2
N2—C10—C8106.78 (18)C17—C16—H16B109.2
C8—C7—C6117.4 (2)H16A—C16—H16B107.9
C8—C7—H7121.3N2—C18—C9102.43 (17)
C6—C7—H7121.3N2—C18—H18A111.3
N2—C11—C12111.07 (18)C9—C18—H18A111.3
N2—C11—H11A109.4N2—C18—H18B111.3
C12—C11—H11A109.4C9—C18—H18B111.3
N2—C11—H11B109.4H18A—C18—H18B109.2
C12—C11—H11B109.4H1W—O1W—H2W107 (4)
H11A—C11—H11B108.0
C9—N1—C5—C4−179.8 (2)C7—C8—C10—N2179.0 (3)
C9—N1—C5—C60.1 (3)C9—C8—C10—N2−0.9 (3)
C7—C6—C5—N1−1.1 (4)C9—C8—C7—C60.4 (3)
C1—C6—C5—N1178.7 (2)C10—C8—C7—C6−179.5 (2)
C7—C6—C5—C4178.7 (2)C1—C6—C7—C8−179.0 (2)
C1—C6—C5—C4−1.4 (3)C5—C6—C7—C80.8 (3)
N1—C5—C4—C3−178.7 (2)C10—N2—C11—C12137.0 (2)
C6—C5—C4—C31.5 (4)C18—N2—C11—C12−44.5 (3)
C7—C6—C1—C2179.8 (2)C14—N3—C13—C1275.8 (3)
C5—C6—C1—C20.0 (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—C31.5 (4)N3—C13—C12—C11177.1 (2)
C4—C3—C2—C1−1.4 (4)C16—O2—C15—C1456.8 (4)
C5—N1—C9—C81.3 (4)C14—N3—C17—C16−58.6 (3)
C5—N1—C9—C18179.5 (2)C13—N3—C17—C16176.7 (2)
N1—C9—C8—C7−1.6 (4)C17—N3—C14—C1559.0 (3)
C18—C9—C8—C7180.0 (2)C13—N3—C14—C15−176.9 (2)
N1—C9—C8—C10178.3 (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—O10.3 (4)N3—C17—C16—O259.1 (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—C9179.7 (2)
C18—N2—C10—C81.6 (3)N1—C9—C18—N2−177.5 (2)
C7—C8—C10—O1−1.1 (5)C8—C9—C18—N21.0 (3)
C9—C8—C10—O1179.0 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1W—H1W···N3i0.86 (4)2.15 (4)2.961 (4)155 (4)
O1W—H2W···O1ii0.87 (4)1.98 (4)2.843 (3)174 (4)
C11—H11B···O1W0.972.473.326 (4)147

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5085).

References

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