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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 2| February 2008| Page o448
doi:10.1107/S1600536807066251

(S)-2-(3-Nitro­phen­yl)-1,2-di­hydro­quinazolin-4(3H)-one

Lijun Zhang,a Jiarong Li,a* Daxin Shi,a Ling Zhanga and Yanqiu Fana

aSchool of Chemical Engineering & the Environment, Beijing Institute of Technology, Beijing 100081, People's Republic of China
*Correspondence e-mail: jrli@bit.edu.cn

(Received 20 November 2007; accepted 9 December 2007; online 16 January 2008)

In the racemic title compound, C14H11N3O3, the pyrimidine ring has an envelope conformation with the puckering parameters Q = 0.3338 (17) Å, Θ = 60.1 (3) and φ = 290.4 (3)°. The two N—H groups form hydrogen bonds with symmetry-related mol­ecules, building a two-dimensional network parallel to the (10[\overline{1}]) plane.

Related literature

For related literature, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]); Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]); Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]); Chen et al. (2007[Chen, K., Al Aowad, A. F., Adelstein, S. J. & Kassis, A. I. (2007). J. Med. Chem. 50, 663-673.]).

[Scheme 1]

Experimental

Crystal data

  • C14H11N3O3

  • Mr = 269.26

  • Monoclinic, P 21 /n

  • a = 10.9766 (13) Å

  • b = 9.8626 (9) Å

  • c = 11.7636 (14) Å

  • β = 109.697 (7)°

  • V = 1199.0 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 113 (2) K

  • 0.16 × 0.12 × 0.10 mm
Data collection

  • Rigaku Saturn diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2004[Rigaku (2004). CrystalClear. Version 1.36. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.981, Tmax = 0.988

  • 12847 measured reflections

  • 2358 independent reflections

  • 2209 reflections with I > 2σ(I)

  • Rint = 0.043
Refinement

  • R[F2 > 2σ(F2)] = 0.053

  • wR(F2) = 0.134

  • S = 1.15

  • 2358 reflections

  • 187 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.27 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1⋯O1i 0.857 (9) 2.075 (10) 2.9318 (19) 179.3 (19)
N2—H2⋯O1ii 0.853 (9) 2.165 (11) 2.9837 (18) 160.9 (17)
Symmetry codes: (i) -x+1, -y+1, -z; (ii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: CrystalClear (Rigaku, 2004[Rigaku (2004). CrystalClear. Version 1.36. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXL97 and SHELXS97. University of Göttingen, Germany.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXL97 and SHELXS97. University of Göttingen, Germany.]); molecular graphics: ORTEPIII (Burnett & Johnson, 1996[Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA.]), ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and CAMERON (Watkin et al., 1993[Watkin, D. M., Pearce, L. & Prout, C. K. (1993). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807066251/dn2300sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536807066251/dn2300Isup2.hkl

checkCIF report


Comment top

The title compound (I), C~14~H~11Ñ~3Õ~3~, a derivative of the most useful 1,2-dihydroquinazolinones (Chen et al., 2007), was synthesized directly from the reaction of 2-aminobenzonitrile and 3-nitrobenzaldehyde. In order to further confirm its structure and determine the correlation of structural features with biological activity, its single-crystal was undertaken.

The title compound (I), C14H11N3O3, is built up from dihydroquinazolin made by two six membered fused rings and a nitrophenyl ring linked through a C—C single bond (Fig. 1). The pyrimidine ring has an enveloppe conformation (Cremer & Pople, 1975) with the puckering Amplitude (Q) = 0.3338 (17) Å, Θ = 60.1 (3) ° and ϕ = 290.4 (3) °.

The two N—H groups form O—H···O hydrogen bonds with the ketone O atom of symmetry related molecules. Two N—H groups of symmetry related moleules form an R22(8) motif (Etter et al., 1990; Bernstein et al., 1995) whereas the other N—H group links these motifs to each other building a two dimensionnal network parallel to the (1 0 - 1) plane (Table 1, Fig. 2).

Related literature top

For related literature, see: Bernstein et al. (1995); Cremer & Pople (1975); Etter et al. (1990); Chen et al. (2007).

Experimental top

The title compound was obtained from the reaction of 2-aminobenzonitrile with 3-nitrobenzaldehyde in the present of zinc chloride, refluxing for 1.5 h in DMF and its single-crystal was cultured from a solution of ethanol by slow evaporation at room temperature.

Mp. 210–212°C. Spectra data: IR (KBr, cm-1): 3296, 3188, 1653, 1610, 1532, 1353; 1H NMR (DMSO-d6) δH: 5.95 (1H, s, CH), 6.70 (1H, t, J=7.6 Hz, ArH), 6.79 (1H, d, J=8.0 Hz, ArH), 7.29 (1H, t, J=8.0 Hz, ArH), 7.35 (1H, s, NH), 7.62 (1H, dd, J=7.6 Hz, ArH), 7.70 (1H, t, J=7.6 Hz, ArH), 7.94 (1H, d, J=7.6 Hz, ArH), 8.21–8.22 (1H, m, J=1.4, 1.4 Hz, ArH), 8.36 (1H, t, J=1.8, 1.8 Hz, ArH), 8.53 (1H, s, NH); 13C NMR (DMSO-d6) δC: 65.20, 114.61, 114.97, 117.55, 121.59, 123.29, 127.43, 130.06, 133.39, 133.59, 144.32, 147.32, 147.73, 163.36; MS (ESI): m/z (%) =270.1 (100) [M+H]+; C14H11N3O3: calcd. C 62.45, H 4.12, N 15.61; found C 62.16, H 4.20, N 15.24.

Refinement top

All H atoms attached to C atoms were fixed geometrically and treated as riding with C—H = 0.93 Å (aromatic) or 0.98 Å (methine) with Uiso(H) = 1.2Ueq(C). H atoms attached to N were located in difference Fourier maps and included in the subsequent refinement using restraints (O—N= 0.85 (1) Å) with Uiso(H) = 1.2Ueq(N).

Computing details top

Data collection: CrystalClear (Rigaku, 2004); cell refinement: CrystalClear (Rigaku, 2004); data reduction: CrystalClear (Rigaku, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997), and CAMERON (Watkin et al., 1993); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) with atom the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.
[Figure 2] Fig. 2. Partial packing showing one sheet of molecules connected by N—H···O hydrogen bonds (dashed lines). H atoms not involved in hydrogen bondings have been omitted for clarity.
(S)-2-(3-Nitrophenyl)-1,2-dihydroquinazolin-4(3H)-one top
Crystal data top
C14H11N3O3F(000) = 560
Mr = 269.26Dx = 1.492 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ynCell parameters from 4115 reflections
a = 10.9766 (13) Åθ = 1.8–27.9°
b = 9.8626 (9) ŵ = 0.11 mm−1
c = 11.7636 (14) ÅT = 113 K
β = 109.697 (7)°Block, yellow
V = 1199.0 (2) Å30.16 × 0.12 × 0.10 mm
Z = 4
Data collection top
Rigaku Saturn
diffractometer		2358 independent reflections
Radiation source: rotating anode2209 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.043
Detector resolution: 14.63 pixels mm-1θmax = 26.0°, θmin = 2.2°
ω scansh = −13→13
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2004)		k = −12→12
Tmin = 0.981, Tmax = 0.988l = −14→14
12847 measured reflections
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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134H atoms treated by a mixture of independent and constrained refinement
S = 1.15 w = 1/[σ2(Fo2) + (0.0628P)2 + 0.2875P]
where P = (Fo2 + 2Fc2)/3
2358 reflections(Δ/σ)max = 0.001
187 parametersΔρmax = 0.30 e Å−3
2 restraintsΔρmin = −0.27 e Å−3
Crystal data top
C14H11N3O3V = 1199.0 (2) Å3
Mr = 269.26Z = 4
Monoclinic, P21/nMo Kα radiation
a = 10.9766 (13) ŵ = 0.11 mm−1
b = 9.8626 (9) ÅT = 113 K
c = 11.7636 (14) Å0.16 × 0.12 × 0.10 mm
β = 109.697 (7)°
Data collection top
Rigaku Saturn
diffractometer		2358 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2004)		2209 reflections with I > 2σ(I)
Tmin = 0.981, Tmax = 0.988Rint = 0.043
12847 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0532 restraints
wR(F2) = 0.134H atoms treated by a mixture of independent and constrained refinement
S = 1.15Δρmax = 0.30 e Å−3
2358 reflectionsΔρmin = −0.27 e Å−3
187 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.38313 (11)0.37578 (12)0.01748 (10)0.0300 (3)
O20.88573 (16)0.82212 (18)0.63964 (16)0.0661 (6)
O31.00163 (13)0.66568 (15)0.59857 (12)0.0405 (4)
N10.59073 (14)0.40329 (15)0.13946 (12)0.0251 (3)
H10.5980 (18)0.4683 (15)0.0939 (15)0.030*
N20.69081 (13)0.25348 (14)0.30194 (13)0.0241 (3)
H20.7543 (14)0.2352 (19)0.3656 (12)0.029*
N30.89721 (16)0.71853 (17)0.58678 (14)0.0369 (4)
C10.47429 (16)0.34319 (17)0.11042 (15)0.0248 (4)
C20.46290 (16)0.23302 (17)0.19167 (14)0.0237 (4)
C30.57453 (16)0.19070 (17)0.28587 (14)0.0226 (4)
C40.56527 (17)0.07855 (17)0.35660 (15)0.0265 (4)
H40.63790.04820.41850.032*
C50.44777 (17)0.01378 (18)0.33363 (16)0.0287 (4)
H50.4425−0.06060.38030.034*
C60.33707 (18)0.05748 (18)0.24215 (16)0.0299 (4)
H60.25840.01380.22880.036*
C70.34564 (17)0.16652 (18)0.17147 (16)0.0272 (4)
H70.27230.19580.10980.033*
C80.69237 (16)0.39113 (17)0.25765 (14)0.0235 (4)
H80.77580.40490.24590.028*
C90.67990 (15)0.49851 (16)0.34659 (14)0.0227 (4)
C100.79123 (16)0.55921 (17)0.42414 (15)0.0248 (4)
H100.87230.53490.42200.030*
C110.77919 (17)0.65619 (17)0.50431 (15)0.0269 (4)
C120.66122 (18)0.69635 (18)0.51111 (16)0.0306 (4)
H120.65600.76330.56490.037*
C130.55171 (18)0.63387 (19)0.43545 (17)0.0326 (4)
H130.47110.65730.43910.039*
C140.56071 (17)0.53628 (18)0.35387 (16)0.0282 (4)
H140.48580.49540.30310.034*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0275 (7)0.0325 (7)0.0214 (6)−0.0004 (5)−0.0029 (5)0.0017 (5)
O20.0589 (11)0.0685 (12)0.0687 (12)−0.0165 (9)0.0185 (9)−0.0473 (10)
O30.0295 (8)0.0512 (9)0.0354 (8)−0.0077 (6)0.0040 (6)−0.0056 (6)
N10.0249 (8)0.0281 (8)0.0182 (7)−0.0030 (6)0.0018 (6)0.0025 (6)
N20.0206 (7)0.0258 (8)0.0206 (7)0.0013 (6)0.0001 (6)0.0013 (6)
N30.0398 (10)0.0399 (10)0.0290 (9)−0.0098 (8)0.0089 (7)−0.0087 (7)
C10.0261 (9)0.0254 (9)0.0202 (9)0.0000 (7)0.0042 (7)−0.0027 (7)
C20.0248 (9)0.0246 (9)0.0194 (8)0.0003 (7)0.0047 (7)−0.0027 (7)
C30.0260 (9)0.0227 (8)0.0183 (8)0.0012 (7)0.0062 (7)−0.0044 (6)
C40.0316 (9)0.0254 (9)0.0210 (9)0.0025 (7)0.0070 (7)−0.0004 (7)
C50.0393 (10)0.0244 (9)0.0246 (9)−0.0023 (8)0.0138 (8)−0.0009 (7)
C60.0305 (10)0.0310 (10)0.0309 (10)−0.0069 (8)0.0138 (8)−0.0067 (7)
C70.0239 (9)0.0313 (9)0.0246 (9)−0.0011 (7)0.0057 (7)−0.0046 (7)
C80.0213 (8)0.0277 (9)0.0183 (8)−0.0019 (7)0.0026 (7)0.0009 (6)
C90.0258 (9)0.0219 (8)0.0188 (8)−0.0004 (7)0.0056 (7)0.0044 (6)
C100.0253 (9)0.0280 (9)0.0204 (8)−0.0023 (7)0.0066 (7)0.0023 (7)
C110.0305 (10)0.0267 (9)0.0205 (9)−0.0050 (7)0.0045 (7)0.0000 (7)
C120.0397 (11)0.0254 (9)0.0256 (9)0.0033 (8)0.0097 (8)−0.0014 (7)
C130.0286 (10)0.0329 (10)0.0343 (10)0.0066 (8)0.0079 (8)0.0000 (8)
C140.0253 (9)0.0279 (9)0.0271 (9)0.0009 (7)0.0034 (7)0.0000 (7)
Geometric parameters (Å, º) top
O1—C11.250 (2)C5—H50.9300
O2—N31.224 (2)C6—C71.382 (2)
O3—N31.224 (2)C6—H60.9300
N1—C11.344 (2)C7—H70.9300
N1—C81.465 (2)C8—C91.527 (2)
N1—H10.857 (9)C8—H80.9800
N2—C31.373 (2)C9—C101.390 (2)
N2—C81.456 (2)C9—C141.390 (2)
N2—H20.853 (9)C10—C111.381 (2)
N3—C111.466 (2)C10—H100.9300
C1—C21.480 (2)C11—C121.382 (3)
C2—C71.392 (2)C12—C131.377 (3)
C2—C31.410 (2)C12—H120.9300
C3—C41.408 (2)C13—C141.386 (3)
C4—C51.382 (2)C13—H130.9300
C4—H40.9300C14—H140.9300
C5—C61.392 (3)
C1—N1—C8124.04 (14)C6—C7—C2120.70 (16)
C1—N1—H1116.9 (13)C6—C7—H7119.7
C8—N1—H1116.9 (13)C2—C7—H7119.7
C3—N2—C8119.58 (14)N2—C8—N1108.59 (13)
C3—N2—H2118.2 (13)N2—C8—C9112.76 (13)
C8—N2—H2114.0 (13)N1—C8—C9112.21 (13)
O3—N3—O2123.41 (17)N2—C8—H8107.7
O3—N3—C11118.77 (15)N1—C8—H8107.7
O2—N3—C11117.82 (17)C9—C8—H8107.7
O1—C1—N1121.41 (16)C10—C9—C14118.78 (16)
O1—C1—C2122.46 (15)C10—C9—C8119.10 (15)
N1—C1—C2116.08 (14)C14—C9—C8122.11 (15)
C7—C2—C3120.22 (16)C11—C10—C9118.77 (16)
C7—C2—C1120.68 (15)C11—C10—H10120.6
C3—C2—C1118.99 (15)C9—C10—H10120.6
N2—C3—C4121.45 (15)C10—C11—C12123.05 (16)
N2—C3—C2119.73 (15)C10—C11—N3118.41 (16)
C4—C3—C2118.70 (16)C12—C11—N3118.53 (16)
C5—C4—C3119.74 (16)C13—C12—C11117.73 (17)
C5—C4—H4120.1C13—C12—H12121.1
C3—C4—H4120.1C11—C12—H12121.1
C4—C5—C6121.46 (17)C12—C13—C14120.52 (17)
C4—C5—H5119.3C12—C13—H13119.7
C6—C5—H5119.3C14—C13—H13119.7
C7—C6—C5119.16 (16)C13—C14—C9121.12 (16)
C7—C6—H6120.4C13—C14—H14119.4
C5—C6—H6120.4C9—C14—H14119.4
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.86 (1)2.08 (1)2.9318 (19)179 (2)
N2—H2···O1ii0.85 (1)2.17 (1)2.9837 (18)161 (2)
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x+1/2, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC14H11N3O3
Mr269.26
Crystal system, space groupMonoclinic, P21/n
Temperature (K)113
a, b, c (Å)10.9766 (13), 9.8626 (9), 11.7636 (14)
β (°) 109.697 (7)
V (Å3)1199.0 (2)
Z4
Radiation typeMo Kα
µ (mm−1)0.11
Crystal size (mm)0.16 × 0.12 × 0.10
Data collection
DiffractometerRigaku Saturn
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2004)
Tmin, Tmax0.981, 0.988
No. of measured, independent and
observed [I > 2σ(I)] reflections		12847, 2358, 2209
Rint0.043
(sin θ/λ)max (Å−1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.134, 1.15
No. of reflections2358
No. of parameters187
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.30, −0.27

Computer programs: CrystalClear (Rigaku, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997), and CAMERON (Watkin et al., 1993).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.857 (9)2.075 (10)2.9318 (19)179.3 (19)
N2—H2···O1ii0.853 (9)2.165 (11)2.9837 (18)160.9 (17)
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x+1/2, −y+1/2, z+1/2.
 

Acknowledgements

We thank Beijing Institute of Technology for financial support and Naikai University for the X-ray diffraction analysis.

References

First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science Google Scholar
 First citationBurnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA.  Google Scholar
 First citationChen, K., Al Aowad, A. F., Adelstein, S. J. & Kassis, A. I. (2007). J. Med. Chem. 50, 663–673.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationCremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.  CrossRef CAS Web of Science Google Scholar
 First citationEtter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256–262.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationRigaku (2004). CrystalClear. Version 1.36. Rigaku Corporation, Tokyo, Japan.  Google Scholar
 First citationSheldrick, G. M. (1997). SHELXL97 and SHELXS97. University of Göttingen, Germany.  Google Scholar
 First citationWatkin, D. M., Pearce, L. & Prout, C. K. (1993). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England.  Google Scholar

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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 2| February 2008| Page o448
doi:10.1107/S1600536807066251
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