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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): o2989.
Published online 2009 November 4. doi:  10.1107/S1600536809045516
PMCID: PMC2971964

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

Abstract

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

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

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Object name is e-65-o2989-scheme1.jpg

Experimental

Crystal data

  • C16H16N4O·0.5CH4O
  • M r = 296.35
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2989-efi1.jpg
  • a = 19.5972 (11) Å
  • b = 12.2035 (7) Å
  • c = 12.8681 (8) Å
  • β = 103.301 (1)°
  • V = 2994.9 (3) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 295 K
  • 0.30 × 0.20 × 0.10 mm

Data collection

  • Bruker APEXII diffractometer
  • Absorption correction: none
  • 14007 measured reflections
  • 3399 independent reflections
  • 2377 reflections with I > 2σ(I)
  • R int = 0.073

Refinement

  • R[F 2 > 2σ(F 2)] = 0.062
  • wR(F 2) = 0.186
  • S = 1.09
  • 3399 reflections
  • 210 parameters
  • 13 restraints
  • H-atom parameters constrained
  • Δρmax = 0.55 e Å−3
  • Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809045516/bt5121sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045516/bt5121Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Experimental

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

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.

Figures

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.

Crystal data

C16H16N4O·0.5CH4OF(000) = 1256
Mr = 296.35Dx = 1.314 Mg m3
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 mm1
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

Bruker APEXII diffractometer2377 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

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 = 1.09w = 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 Å3
13 restraintsΔρmin = −0.29 e Å3

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

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)

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, °)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5121).

References

  • 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. [PubMed]
  • Westrip, S. P. (2009). publCIF. In preparation.
  • Yang, X.-H., Chen, X.-B. & Zhou, S.-X. (2009). Acta Cryst. E65, o185–o186. [PMC free article] [PubMed]
  • 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.

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