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Acta Cryst. (2009). E65, o2989    [ doi:10.1107/S1600536809045516 ]

3-(2-Aminoethyl)-2-anilinoquinazolin-4(3H)-one methanol hemisolvate

T. Gao, Y.-H. Jiao and S. W. Ng

Abstract top

The title methanol hemisolvated quinazolin-(3H)-one, C16H16N4O·0.5CH3OH, has an anilino substituent in the 2-position and an aminoethyl substituent in the 3-position of the planar fused-ring system (r.m.s. deviation = 0.019 Å). The anilino N atom donates an intramolecular hydrogen bond to the aminoethyl N atom. The molecule and the solvent methanol molecule are linked by N-H...N, N-H...O and O-H...O hydrogen bonds. The methanol molecule is disordered over two equally occupied positions about a twofold rotation axis.

Related literature top

For the synthesis of this class of compounds, see: Yang et al. (2008). For the crystal structure of a chlorine-substituted derivative, see: Yang et al. (2009).

Experimental top

To a THF (10 ml) solution of 2-ethoxycarbonyliminophosphorane (1.27 g, 3.0 mmol) was added phenylisocyanate (0.36 g, 3.0 mmol). The solution was set aside undisturbed for 6 h at 273 K. To this solution was added ethanolamine (0.18 g, 3 mmol) in THF (5 ml). The mixture was stirred overnight. The solvent was removed and the solid recrystallized from a chloroform/methanol (1/1) mixture to give colorless crystals in 80% yield; m.p. 433–434 K.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.97 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5U(C). The amino and hydroxy H atoms were similarly generated.

The methanol molecule is disordered over two equally occupied positions about a two-fold rotation axis. The C–O distance was restrained to 1.500±0.002 Å. The anisotropic displacemnt parameters of the methanolic O and C atoms were restrained to be nearly isotropic.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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, 2009).

Figures top
[Figure 1] Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of the title compound at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
3-(2-Aminoethyl)-2-anilinoquinazolin-4(3H)-one methanol hemisolvate top
Crystal data top
C16H16N4O·0.5CH4OF(000) = 1256
Mr = 296.35Dx = 1.314 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 3816 reflections
a = 19.5972 (11) Åθ = 2.4–25.9°
b = 12.2035 (7) ŵ = 0.09 mm−1
c = 12.8681 (8) ÅT = 295 K
β = 103.301 (1)°Block, colorless
V = 2994.9 (3) Å30.30 × 0.20 × 0.10 mm
Z = 8
Data collection top
Bruker APEXII
diffractometer		2377 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.073
graphiteθmax = 27.5°, θmin = 2.0°
ω scansh = −17→25
14007 measured reflectionsk = −15→14
3399 independent reflectionsl = −16→16
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.186H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.1044P)2 + 0.1504P]
where P = (Fo2 + 2Fc2)/3
3399 reflections(Δ/σ)max = 0.001
210 parametersΔρmax = 0.55 e Å−3
13 restraintsΔρmin = −0.29 e Å−3
Crystal data top
C16H16N4O·0.5CH4OV = 2994.9 (3) Å3
Mr = 296.35Z = 8
Monoclinic, C2/cMo Kα radiation
a = 19.5972 (11) ŵ = 0.09 mm−1
b = 12.2035 (7) ÅT = 295 K
c = 12.8681 (8) Å0.30 × 0.20 × 0.10 mm
β = 103.301 (1)°
Data collection top
Bruker APEXII
diffractometer		Rint = 0.073
14007 measured reflectionsθmax = 27.5°
3399 independent reflectionsStandard reflections: 0
2377 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.062H-atom parameters constrained
wR(F2) = 0.186Δρmax = 0.55 e Å−3
S = 1.09Δρmin = −0.29 e Å−3
3399 reflectionsAbsolute structure: ?
210 parametersFlack parameter: ?
13 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.68958 (7)0.41303 (12)0.81309 (11)0.0573 (4)
N10.73674 (8)0.41620 (12)0.66714 (11)0.0424 (4)
N20.84958 (8)0.34284 (13)0.67038 (11)0.0458 (4)
N30.77752 (9)0.40366 (13)0.51241 (12)0.0498 (4)
H310.73450.42390.48170.060*
N40.63136 (9)0.37965 (16)0.44490 (14)0.0632 (5)
H410.61310.42630.39390.076*
H420.61310.31430.42840.076*
C10.80430 (10)0.34133 (14)0.83148 (13)0.0414 (4)
C20.81360 (11)0.31401 (16)0.93932 (14)0.0503 (5)
H20.77820.32900.97460.060*
C30.87449 (12)0.26533 (18)0.99341 (15)0.0576 (6)
H30.88040.24651.06500.069*
C40.92707 (11)0.24457 (19)0.94030 (15)0.0589 (6)
H40.96840.21150.97670.071*
C50.91908 (11)0.27202 (19)0.83510 (16)0.0573 (6)
H50.95520.25790.80110.069*
C60.85720 (10)0.32115 (15)0.77791 (13)0.0427 (5)
C70.73916 (10)0.39143 (15)0.77321 (14)0.0437 (5)
C80.79099 (10)0.38642 (15)0.61962 (14)0.0414 (4)
C90.82431 (10)0.39287 (14)0.44502 (14)0.0426 (5)
C100.79487 (10)0.36669 (15)0.33875 (14)0.0462 (5)
H100.74720.35150.31750.055*
C110.83579 (12)0.36311 (17)0.26507 (15)0.0530 (5)
H110.81540.34620.19420.064*
C120.90627 (13)0.38417 (19)0.29508 (18)0.0614 (6)
H120.93380.38200.24510.074*
C130.93592 (12)0.40868 (19)0.40098 (18)0.0616 (6)
H130.98380.42250.42200.074*
C140.89551 (11)0.41293 (17)0.47595 (16)0.0534 (5)
H140.91610.42920.54680.064*
C150.67613 (10)0.48235 (17)0.61029 (15)0.0516 (5)
H15A0.69220.53350.56340.062*
H15B0.65870.52480.66240.062*
C160.61626 (11)0.41579 (18)0.54480 (17)0.0586 (6)
H16A0.60800.35240.58570.070*
H16B0.57390.45990.52980.070*
O20.5495 (3)0.4637 (6)0.7850 (7)0.176 (3)0.50
H2O0.58560.42440.80060.211*0.50
C170.4883 (4)0.3949 (6)0.7344 (11)0.101 (3)0.50
H17A0.45530.39370.77920.152*0.50
H17B0.50370.32160.72540.152*0.50
H17C0.46620.42500.66600.152*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0468 (8)0.0701 (10)0.0607 (8)0.0019 (7)0.0243 (7)−0.0043 (6)
N10.0402 (9)0.0437 (9)0.0438 (8)0.0002 (7)0.0110 (7)−0.0028 (6)
N20.0417 (9)0.0570 (10)0.0402 (8)0.0011 (7)0.0130 (7)−0.0002 (6)
N30.0430 (9)0.0665 (11)0.0405 (8)0.0019 (8)0.0107 (7)0.0053 (7)
N40.0614 (12)0.0661 (12)0.0558 (10)0.0053 (9)0.0006 (9)−0.0015 (8)
C10.0435 (10)0.0412 (10)0.0411 (9)−0.0070 (8)0.0128 (8)−0.0050 (7)
C20.0578 (13)0.0540 (12)0.0437 (10)−0.0063 (10)0.0214 (9)−0.0038 (8)
C30.0697 (14)0.0649 (13)0.0384 (9)−0.0019 (11)0.0128 (10)0.0028 (9)
C40.0490 (12)0.0744 (15)0.0494 (11)0.0035 (11)0.0035 (10)0.0062 (9)
C50.0446 (12)0.0782 (15)0.0510 (11)0.0058 (10)0.0152 (9)0.0035 (10)
C60.0424 (10)0.0490 (11)0.0378 (9)−0.0038 (8)0.0112 (8)−0.0014 (7)
C70.0443 (11)0.0438 (10)0.0459 (10)−0.0063 (8)0.0164 (8)−0.0070 (7)
C80.0413 (10)0.0424 (10)0.0415 (9)−0.0040 (8)0.0112 (8)−0.0027 (7)
C90.0445 (11)0.0432 (10)0.0411 (9)−0.0007 (8)0.0122 (8)0.0067 (7)
C100.0482 (11)0.0448 (11)0.0440 (9)−0.0001 (8)0.0072 (8)0.0011 (7)
C110.0636 (14)0.0570 (12)0.0404 (9)0.0007 (10)0.0159 (9)−0.0006 (8)
C120.0654 (15)0.0711 (15)0.0554 (12)0.0043 (11)0.0293 (11)0.0041 (10)
C130.0466 (12)0.0792 (16)0.0620 (13)−0.0042 (10)0.0187 (10)0.0085 (10)
C140.0490 (12)0.0683 (14)0.0423 (10)−0.0097 (10)0.0091 (9)0.0032 (9)
C150.0507 (12)0.0492 (12)0.0548 (11)0.0090 (9)0.0119 (9)−0.0007 (8)
C160.0445 (12)0.0671 (14)0.0618 (13)0.0074 (10)0.0071 (10)0.0025 (10)
O20.109 (4)0.189 (6)0.231 (6)−0.017 (4)0.043 (4)−0.115 (5)
C170.044 (6)0.143 (5)0.117 (8)0.021 (4)0.017 (5)0.021 (5)
Geometric parameters (Å, °) top
O1—C71.227 (2)C5—H50.9300
N1—C71.388 (2)C9—C141.382 (3)
N1—C81.391 (2)C9—C101.394 (2)
N1—C151.482 (2)C10—C111.376 (3)
N2—C81.297 (2)C10—H100.9300
N2—C61.383 (2)C11—C121.370 (3)
N3—C81.360 (2)C11—H110.9300
N3—C91.406 (2)C12—C131.386 (3)
N3—H310.8800C12—H120.9300
N4—C161.453 (3)C13—C141.383 (3)
N4—H410.8800C13—H130.9300
N4—H420.8800C14—H140.9300
C1—C61.393 (3)C15—C161.514 (3)
C1—C21.398 (2)C15—H15A0.9700
C1—C71.458 (3)C15—H15B0.9700
C2—C31.371 (3)C16—H16A0.9700
C2—H20.9300C16—H16B0.9700
C3—C41.385 (3)O2—C171.486 (2)
C3—H30.9300O2—H2O0.8400
C4—C51.368 (3)C17—H17A0.9600
C4—H40.9300C17—H17B0.9600
C5—C61.400 (3)C17—H17C0.9600
C7—N1—C8121.23 (15)N2—C8—N1124.28 (16)
C7—N1—C15116.50 (15)N3—C8—N1114.57 (16)
C8—N1—C15122.13 (15)C14—C9—C10119.07 (18)
C8—N2—C6117.49 (16)C14—C9—N3124.37 (17)
C8—N3—C9127.54 (17)C10—C9—N3116.44 (17)
C8—N3—H31116.2C11—C10—C9120.53 (19)
C9—N3—H31116.2C11—C10—H10119.7
C16—N4—H41109.5C9—C10—H10119.7
C16—N4—H42109.5C12—C11—C10120.61 (19)
H41—N4—H42109.5C12—C11—H11119.7
C6—C1—C2120.49 (17)C10—C11—H11119.7
C6—C1—C7118.89 (16)C11—C12—C13119.0 (2)
C2—C1—C7120.62 (18)C11—C12—H12120.5
C3—C2—C1120.45 (19)C13—C12—H12120.5
C3—C2—H2119.8C14—C13—C12121.1 (2)
C1—C2—H2119.8C14—C13—H13119.5
C2—C3—C4119.24 (17)C12—C13—H13119.5
C2—C3—H3120.4C9—C14—C13119.66 (19)
C4—C3—H3120.4C9—C14—H14120.2
C5—C4—C3120.99 (19)C13—C14—H14120.2
C5—C4—H4119.5N1—C15—C16114.39 (17)
C3—C4—H4119.5N1—C15—H15A108.7
C4—C5—C6120.9 (2)C16—C15—H15A108.7
C4—C5—H5119.6N1—C15—H15B108.7
C6—C5—H5119.6C16—C15—H15B108.7
N2—C6—C1122.70 (17)H15A—C15—H15B107.6
N2—C6—C5119.27 (17)N4—C16—C15111.46 (19)
C1—C6—C5117.96 (16)N4—C16—H16A109.3
O1—C7—N1120.87 (17)C15—C16—H16A109.3
O1—C7—C1123.97 (17)N4—C16—H16B109.3
N1—C7—C1115.15 (16)C15—C16—H16B109.3
N2—C8—N3121.13 (18)H16A—C16—H16B108.0
C6—C1—C2—C3−1.1 (3)C6—N2—C8—N3−175.64 (16)
C7—C1—C2—C3178.97 (17)C6—N2—C8—N12.5 (3)
C1—C2—C3—C40.7 (3)C9—N3—C8—N2−9.1 (3)
C2—C3—C4—C50.1 (3)C9—N3—C8—N1172.63 (16)
C3—C4—C5—C6−0.5 (4)C7—N1—C8—N2−6.1 (3)
C8—N2—C6—C11.8 (3)C15—N1—C8—N2169.49 (18)
C8—N2—C6—C5178.68 (18)C7—N1—C8—N3172.12 (15)
C2—C1—C6—N2177.50 (16)C15—N1—C8—N3−12.3 (2)
C7—C1—C6—N2−2.5 (3)C8—N3—C9—C14−31.8 (3)
C2—C1—C6—C50.6 (3)C8—N3—C9—C10152.29 (18)
C7—C1—C6—C5−179.41 (17)C14—C9—C10—C11−1.4 (3)
C4—C5—C6—N2−176.84 (19)N3—C9—C10—C11174.75 (17)
C4—C5—C6—C10.2 (3)C9—C10—C11—C120.6 (3)
C8—N1—C7—O1−176.29 (16)C10—C11—C12—C130.3 (3)
C15—N1—C7—O17.9 (3)C11—C12—C13—C14−0.5 (3)
C8—N1—C7—C14.9 (2)C10—C9—C14—C131.2 (3)
C15—N1—C7—C1−170.91 (15)N3—C9—C14—C13−174.6 (2)
C6—C1—C7—O1−179.64 (17)C12—C13—C14—C9−0.3 (3)
C2—C1—C7—O10.3 (3)C7—N1—C15—C16−96.6 (2)
C6—C1—C7—N1−0.9 (2)C8—N1—C15—C1687.6 (2)
C2—C1—C7—N1179.07 (16)N1—C15—C16—N4−77.5 (2)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N3—H31···N40.882.042.811 (3)146
N4—H41···O2i0.882.132.990 (6)168
O2—H2O···O10.842.012.755 (6)147
Symmetry codes: (i) x, −y+1, z−1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N3—H31···N40.882.042.811 (3)146
N4—H41···O2i0.882.132.990 (6)168
O2—H2O···O10.842.012.755 (6)147
Symmetry codes: (i) x, −y+1, z−1/2.
Acknowledgements top

We thank Xianning University, Huangshi Institute of Technology and the University of Malaya for supporting this study.

references
References top

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.

Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Westrip, S. P. (2009). publCIF. In preparation.

Yang, X.-H., Chen, X.-B. & Zhou, S.-X. (2009). Acta Cryst. E65, o185–o186.

Yang, X.-H., Wu, M.-H., Sun, S.-F., Ding, M.-W., Xie, J.-L. & Xia, Q.-H. (2008). J. Heterocycl. Chem. 45, 1365–1369.