(S)-2-(3-Nitro-phen-yl)-1,2-dihydro-quinazolin-4(3H)-one.

In the racemic title compound, C(14)H(11)N(3)O(3), 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 mol-ecules, building a two-dimensional network parallel to the (10) plane.

Related literature

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

Experimental

Crystal data

C14H11N3O3

M = 269.26

Monoclinic,

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 ▶) T min = 0.981, T max = 0.988

12847 measured reflections

2358 independent reflections

2209 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 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

Data collection: CrystalClear (Rigaku, 2004 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

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

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

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

C14H11N3O3	F000 = 560
Mr = 269.26	Dx = 1.492 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71070 Å
Hall symbol: -P 2yn	Cell parameters from 4115 reflections
a = 10.9766 (13) Å	θ = 1.8–27.9º
b = 9.8626 (9) Å	µ = 0.11 mm−1
c = 11.7636 (14) Å	T = 113 (2) K
β = 109.697 (7)º	Block, yellow
V = 1199.0 (2) Å3	0.16 × 0.12 × 0.10 mm
Z = 4

Rigaku Saturn diffractometer	2358 independent reflections
Radiation source: rotating anode	2209 reflections with I > 2σ(I)
Monochromator: confocal	Rint = 0.043
Detector resolution: 14.63 pixels mm-1	θmax = 26.0º
T = 113(2) K	θmin = 2.2º
ω scans	h = −13→13
Absorption correction: multi-scan(CrystalClear; Rigaku, 2004)	k = −12→12
Tmin = 0.981, Tmax = 0.988	l = −14→14
12847 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.134	w = 1/[σ2(Fo2) + (0.0628P)2 + 0.2875P] where P = (Fo2 + 2Fc2)/3
S = 1.15	(Δ/σ)max = 0.001
2358 reflections	Δρmax = 0.30 e Å−3
187 parameters	Δρmin = −0.27 e Å−3
2 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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.

	x	y	z	Uiso*/Ueq
O1	0.38313 (11)	0.37578 (12)	0.01748 (10)	0.0300 (3)
O2	0.88573 (16)	0.82212 (18)	0.63964 (16)	0.0661 (6)
O3	1.00163 (13)	0.66568 (15)	0.59857 (12)	0.0405 (4)
N1	0.59073 (14)	0.40329 (15)	0.13946 (12)	0.0251 (3)
H1	0.5980 (18)	0.4683 (15)	0.0939 (15)	0.030*
N2	0.69081 (13)	0.25348 (14)	0.30194 (13)	0.0241 (3)
H2	0.7543 (14)	0.2352 (19)	0.3656 (12)	0.029*
N3	0.89721 (16)	0.71853 (17)	0.58678 (14)	0.0369 (4)
C1	0.47429 (16)	0.34319 (17)	0.11042 (15)	0.0248 (4)
C2	0.46290 (16)	0.23302 (17)	0.19167 (14)	0.0237 (4)
C3	0.57453 (16)	0.19070 (17)	0.28587 (14)	0.0226 (4)
C4	0.56527 (17)	0.07855 (17)	0.35660 (15)	0.0265 (4)
H4	0.6379	0.0482	0.4185	0.032*
C5	0.44777 (17)	0.01378 (18)	0.33363 (16)	0.0287 (4)
H5	0.4425	−0.0606	0.3803	0.034*
C6	0.33707 (18)	0.05748 (18)	0.24215 (16)	0.0299 (4)
H6	0.2584	0.0138	0.2288	0.036*
C7	0.34564 (17)	0.16652 (18)	0.17147 (16)	0.0272 (4)
H7	0.2723	0.1958	0.1098	0.033*
C8	0.69237 (16)	0.39113 (17)	0.25765 (14)	0.0235 (4)
H8	0.7758	0.4049	0.2459	0.028*
C9	0.67990 (15)	0.49851 (16)	0.34659 (14)	0.0227 (4)
C10	0.79123 (16)	0.55921 (17)	0.42414 (15)	0.0248 (4)
H10	0.8723	0.5349	0.4220	0.030*
C11	0.77919 (17)	0.65619 (17)	0.50431 (15)	0.0269 (4)
C12	0.66122 (18)	0.69635 (18)	0.51111 (16)	0.0306 (4)
H12	0.6560	0.7633	0.5649	0.037*
C13	0.55171 (18)	0.63387 (19)	0.43545 (17)	0.0326 (4)
H13	0.4711	0.6573	0.4391	0.039*
C14	0.56071 (17)	0.53628 (18)	0.35387 (16)	0.0282 (4)
H14	0.4858	0.4954	0.3031	0.034*

	U11	U22	U33	U12	U13	U23
O1	0.0275 (7)	0.0325 (7)	0.0214 (6)	−0.0004 (5)	−0.0029 (5)	0.0017 (5)
O2	0.0589 (11)	0.0685 (12)	0.0687 (12)	−0.0165 (9)	0.0185 (9)	−0.0473 (10)
O3	0.0295 (8)	0.0512 (9)	0.0354 (8)	−0.0077 (6)	0.0040 (6)	−0.0056 (6)
N1	0.0249 (8)	0.0281 (8)	0.0182 (7)	−0.0030 (6)	0.0018 (6)	0.0025 (6)
N2	0.0206 (7)	0.0258 (8)	0.0206 (7)	0.0013 (6)	0.0001 (6)	0.0013 (6)
N3	0.0398 (10)	0.0399 (10)	0.0290 (9)	−0.0098 (8)	0.0089 (7)	−0.0087 (7)
C1	0.0261 (9)	0.0254 (9)	0.0202 (9)	0.0000 (7)	0.0042 (7)	−0.0027 (7)
C2	0.0248 (9)	0.0246 (9)	0.0194 (8)	0.0003 (7)	0.0047 (7)	−0.0027 (7)
C3	0.0260 (9)	0.0227 (8)	0.0183 (8)	0.0012 (7)	0.0062 (7)	−0.0044 (6)
C4	0.0316 (9)	0.0254 (9)	0.0210 (9)	0.0025 (7)	0.0070 (7)	−0.0004 (7)
C5	0.0393 (10)	0.0244 (9)	0.0246 (9)	−0.0023 (8)	0.0138 (8)	−0.0009 (7)
C6	0.0305 (10)	0.0310 (10)	0.0309 (10)	−0.0069 (8)	0.0138 (8)	−0.0067 (7)
C7	0.0239 (9)	0.0313 (9)	0.0246 (9)	−0.0011 (7)	0.0057 (7)	−0.0046 (7)
C8	0.0213 (8)	0.0277 (9)	0.0183 (8)	−0.0019 (7)	0.0026 (7)	0.0009 (6)
C9	0.0258 (9)	0.0219 (8)	0.0188 (8)	−0.0004 (7)	0.0056 (7)	0.0044 (6)
C10	0.0253 (9)	0.0280 (9)	0.0204 (8)	−0.0023 (7)	0.0066 (7)	0.0023 (7)
C11	0.0305 (10)	0.0267 (9)	0.0205 (9)	−0.0050 (7)	0.0045 (7)	0.0000 (7)
C12	0.0397 (11)	0.0254 (9)	0.0256 (9)	0.0033 (8)	0.0097 (8)	−0.0014 (7)
C13	0.0286 (10)	0.0329 (10)	0.0343 (10)	0.0066 (8)	0.0079 (8)	0.0000 (8)
C14	0.0253 (9)	0.0279 (9)	0.0271 (9)	0.0009 (7)	0.0034 (7)	0.0000 (7)

O1—C1	1.250 (2)	C5—H5	0.9300
O2—N3	1.224 (2)	C6—C7	1.382 (2)
O3—N3	1.224 (2)	C6—H6	0.9300
N1—C1	1.344 (2)	C7—H7	0.9300
N1—C8	1.465 (2)	C8—C9	1.527 (2)
N1—H1	0.857 (9)	C8—H8	0.9800
N2—C3	1.373 (2)	C9—C10	1.390 (2)
N2—C8	1.456 (2)	C9—C14	1.390 (2)
N2—H2	0.853 (9)	C10—C11	1.381 (2)
N3—C11	1.466 (2)	C10—H10	0.9300
C1—C2	1.480 (2)	C11—C12	1.382 (3)
C2—C7	1.392 (2)	C12—C13	1.377 (3)
C2—C3	1.410 (2)	C12—H12	0.9300
C3—C4	1.408 (2)	C13—C14	1.386 (3)
C4—C5	1.382 (2)	C13—H13	0.9300
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.392 (3)
C1—N1—C8	124.04 (14)	C6—C7—C2	120.70 (16)
C1—N1—H1	116.9 (13)	C6—C7—H7	119.7
C8—N1—H1	116.9 (13)	C2—C7—H7	119.7
C3—N2—C8	119.58 (14)	N2—C8—N1	108.59 (13)
C3—N2—H2	118.2 (13)	N2—C8—C9	112.76 (13)
C8—N2—H2	114.0 (13)	N1—C8—C9	112.21 (13)
O3—N3—O2	123.41 (17)	N2—C8—H8	107.7
O3—N3—C11	118.77 (15)	N1—C8—H8	107.7
O2—N3—C11	117.82 (17)	C9—C8—H8	107.7
O1—C1—N1	121.41 (16)	C10—C9—C14	118.78 (16)
O1—C1—C2	122.46 (15)	C10—C9—C8	119.10 (15)
N1—C1—C2	116.08 (14)	C14—C9—C8	122.11 (15)
C7—C2—C3	120.22 (16)	C11—C10—C9	118.77 (16)
C7—C2—C1	120.68 (15)	C11—C10—H10	120.6
C3—C2—C1	118.99 (15)	C9—C10—H10	120.6
N2—C3—C4	121.45 (15)	C10—C11—C12	123.05 (16)
N2—C3—C2	119.73 (15)	C10—C11—N3	118.41 (16)
C4—C3—C2	118.70 (16)	C12—C11—N3	118.53 (16)
C5—C4—C3	119.74 (16)	C13—C12—C11	117.73 (17)
C5—C4—H4	120.1	C13—C12—H12	121.1
C3—C4—H4	120.1	C11—C12—H12	121.1
C4—C5—C6	121.46 (17)	C12—C13—C14	120.52 (17)
C4—C5—H5	119.3	C12—C13—H13	119.7
C6—C5—H5	119.3	C14—C13—H13	119.7
C7—C6—C5	119.16 (16)	C13—C14—C9	121.12 (16)
C7—C6—H6	120.4	C13—C14—H14	119.4
C5—C6—H6	120.4	C9—C14—H14	119.4

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)

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) ; (ii) .