Crystal structure of 3-amino-2-ethyl-quinazolin-4(3H)-one.

The mol-ecule of the title compound, C10H11N3O, is planar, including the ethyl group, as indicated by the N-C-C-C torsion angle of 1.5 (2)°. In the crystal, inversion-related mol-ecules are stacked along the a axis. Mol-ecules are oriented head-to-tail and display π-π inter-actions with a centroid-to-centroid distance of 3.6664 (8) Å. N-H⋯O hydrogen bonds between mol-ecules generate a 'step' structure through formation of an R 2 (2)(10) ring.

Related literature

For related compounds, see: Ma et al. (2013 ▸); Adib et al. (2012 ▸); Xu et al. (2012 ▸); Sasmal et al. (2012 ▸); Kumar et al. (2011 ▸); Rohini et al. (2010 ▸); Davies et al. (2010 ▸). For quinazolin-4(3H)-one ring-system modification through li­thia­tion, see: Smith et al. (2004 ▸, 1996 ▸, 1995 ▸). For the crystal structures of related compounds, see: El-Hiti et al. (2014 ▸); Yang et al. (2009 ▸); Coogan et al. (1999 ▸).

Experimental

Crystal data

C10H11N3O

M = 189.22

Triclinic,

a = 7.0230 (5) Å

b = 7.6198 (7) Å

c = 9.7868 (6) Å

α = 69.709 (7)°

β = 89.242 (5)°

γ = 75.191 (7)°

V = 473.27 (7) Å3

Z = 2

Cu Kα radiation

μ = 0.73 mm−1

T = 293 K

0.38 × 0.20 × 0.08 mm

Data collection

Agilent SuperNova Dual Source diffractometer with an Atlas detector

Absorption correction: Gaussian (CrysAlis PRO; Agilent, 2014 ▸) T min = 0.741, T max = 0.924

3303 measured reflections

1858 independent reflections

1657 reflections with I > 2σ(I)

R int = 0.015

Standard reflections: 0

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.196

S = 1.07

1858 reflections

136 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrysAlis PRO (Agilent, 2014 ▸); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: WinGX (Farrugia, 2012 ▸) and CHEMDRAW Ultra (Cambridge Soft, 2001 ▸).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989015014450/hg5454sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015014450/hg5454Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015014450/hg5454Isup3.cml

Click here for additional data file.

10 11 3 . DOI: 10.1107/S2056989015014450/hg5454fig1.tif

The asymmetric unit of C10H11N3O, with atom labels and 50% probability displacement ellipsoids for non-hydrogen atoms.

Click here for additional data file.

. DOI: 10.1107/S2056989015014450/hg5454fig2.tif

Crystal packing with hydrogen-bonding contacts shown as dotted lines.

CCDC reference: 1416070

Additional supporting information: crystallographic information; 3D view; checkCIF report

C10H11N3O	F(000) = 200
Mr = 189.22	Dx = 1.328 Mg m−3
Triclinic, P1	Melting point: 398 K
a = 7.0230 (5) Å	Cu Kα radiation, λ = 1.54184 Å
b = 7.6198 (7) Å	Cell parameters from 1907 reflections
c = 9.7868 (6) Å	θ = 6.5–73.7°
α = 69.709 (7)°	µ = 0.73 mm−1
β = 89.242 (5)°	T = 293 K
γ = 75.191 (7)°	Block, colourless
V = 473.27 (7) Å3	0.38 × 0.20 × 0.08 mm
Z = 2

Agilent SuperNova Dual Source diffractometer with an Atlas detector	1657 reflections with I > 2σ(I)
ω scans	Rint = 0.015
Absorption correction: gaussian (CrysAlis PRO; Agilent, 2014)	θmax = 73.9°, θmin = 6.5°
Tmin = 0.741, Tmax = 0.924	h = −8→8
3303 measured reflections	k = −9→8
1858 independent reflections	l = −10→12

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.061	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.196	w = 1/[σ2(Fo2) + (0.1458P)2 + 0.021P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
1858 reflections	Δρmax = 0.35 e Å−3
136 parameters	Δρmin = −0.22 e Å−3

Experimental. Absorption correction: CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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.

	x	y	z	Uiso*/Ueq
C1	0.26318 (18)	−0.0469 (2)	0.59059 (14)	0.0441 (4)
C2	0.18669 (19)	0.2641 (2)	0.38779 (16)	0.0485 (4)
C3	0.21085 (18)	0.1504 (2)	0.29325 (14)	0.0455 (4)
C4	0.25874 (19)	−0.0513 (2)	0.35723 (14)	0.0453 (4)
C5	0.1873 (2)	0.2421 (3)	0.14073 (16)	0.0585 (4)
H5	0.1547	0.3768	0.0991	0.070*
C6	0.2123 (3)	0.1324 (3)	0.05335 (16)	0.0711 (5)
H6	0.1976	0.1923	−0.0478	0.085*
C7	0.2597 (3)	−0.0691 (3)	0.11692 (19)	0.0738 (5)
H7	0.2761	−0.1428	0.0571	0.089*
C8	0.2829 (3)	−0.1613 (2)	0.26567 (18)	0.0616 (5)
H8	0.3144	−0.2961	0.3059	0.074*
C9	0.2868 (2)	−0.1443 (2)	0.75358 (14)	0.0541 (4)
H9A	0.1644	−0.0989	0.7931	0.065*
H9B	0.3894	−0.1063	0.7928	0.065*
C10	0.3393 (3)	−0.3628 (3)	0.80379 (17)	0.0703 (5)
H10A	0.2385	−0.4018	0.7655	0.105*
H10B	0.3492	−0.4162	0.9087	0.105*
H10C	0.4636	−0.4096	0.7691	0.105*
N1	0.21763 (16)	0.15389 (17)	0.53566 (13)	0.0475 (4)
N2	0.28333 (17)	−0.14907 (17)	0.50721 (12)	0.0479 (4)
N3	0.2043 (3)	0.2510 (2)	0.63756 (16)	0.0683 (5)
O1	0.14455 (19)	0.44171 (16)	0.34527 (14)	0.0704 (4)
H3A	0.080 (3)	0.329 (3)	0.630 (2)	0.079 (6)*
H3B	0.292 (4)	0.328 (5)	0.609 (3)	0.111 (9)*

	U11	U22	U33	U12	U13	U23
C1	0.0404 (6)	0.0519 (7)	0.0392 (7)	−0.0129 (5)	0.0037 (5)	−0.0148 (5)
C2	0.0494 (7)	0.0445 (7)	0.0510 (8)	−0.0144 (5)	0.0072 (5)	−0.0151 (6)
C3	0.0457 (7)	0.0494 (8)	0.0400 (7)	−0.0154 (5)	0.0048 (5)	−0.0122 (6)
C4	0.0494 (7)	0.0498 (7)	0.0403 (7)	−0.0174 (5)	0.0067 (5)	−0.0173 (6)
C5	0.0588 (8)	0.0659 (9)	0.0424 (8)	−0.0201 (7)	0.0043 (6)	−0.0066 (6)
C6	0.0789 (11)	0.0986 (14)	0.0375 (7)	−0.0316 (10)	0.0073 (7)	−0.0206 (8)
C7	0.0926 (12)	0.0963 (13)	0.0520 (9)	−0.0368 (10)	0.0153 (8)	−0.0421 (9)
C8	0.0781 (10)	0.0627 (9)	0.0559 (9)	−0.0253 (8)	0.0121 (7)	−0.0312 (7)
C9	0.0482 (7)	0.0729 (9)	0.0367 (7)	−0.0158 (6)	0.0031 (5)	−0.0142 (6)
C10	0.0729 (10)	0.0711 (10)	0.0464 (8)	−0.0147 (8)	−0.0002 (7)	0.0010 (7)
N1	0.0511 (6)	0.0505 (7)	0.0451 (7)	−0.0128 (5)	0.0045 (4)	−0.0227 (5)
N2	0.0556 (7)	0.0458 (6)	0.0408 (7)	−0.0147 (5)	0.0055 (5)	−0.0129 (5)
N3	0.0801 (10)	0.0733 (9)	0.0628 (9)	−0.0136 (8)	0.0049 (7)	−0.0428 (7)
O1	0.0890 (8)	0.0436 (6)	0.0744 (8)	−0.0149 (5)	0.0118 (6)	−0.0182 (5)

C1—N2	1.2937 (19)	C6—H6	0.9300
C1—N1	1.3840 (19)	C7—C8	1.370 (2)
C1—C9	1.4986 (18)	C7—H7	0.9300
C2—O1	1.2245 (18)	C8—H8	0.9300
C2—N1	1.3853 (19)	C9—C10	1.508 (2)
C2—C3	1.453 (2)	C9—H9A	0.9700
C3—C4	1.394 (2)	C9—H9B	0.9700
C3—C5	1.4027 (19)	C10—H10A	0.9600
C4—N2	1.3862 (18)	C10—H10B	0.9600
C4—C8	1.406 (2)	C10—H10C	0.9600
C5—C6	1.370 (3)	N1—N3	1.4227 (16)
C5—H5	0.9300	N3—H3A	0.91 (2)
C6—C7	1.392 (3)	N3—H3B	0.93 (3)
N2—C1—N1	122.58 (12)	C7—C8—H8	120.1
N2—C1—C9	120.35 (13)	C4—C8—H8	120.1
N1—C1—C9	117.07 (12)	C1—C9—C10	113.52 (13)
O1—C2—N1	120.90 (14)	C1—C9—H9A	108.9
O1—C2—C3	124.96 (14)	C10—C9—H9A	108.9
N1—C2—C3	114.14 (12)	C1—C9—H9B	108.9
C4—C3—C5	120.75 (14)	C10—C9—H9B	108.9
C4—C3—C2	118.64 (13)	H9A—C9—H9B	107.7
C5—C3—C2	120.61 (14)	C9—C10—H10A	109.5
N2—C4—C3	123.07 (12)	C9—C10—H10B	109.5
N2—C4—C8	118.33 (13)	H10A—C10—H10B	109.5
C3—C4—C8	118.60 (14)	C9—C10—H10C	109.5
C6—C5—C3	119.79 (16)	H10A—C10—H10C	109.5
C6—C5—H5	120.1	H10B—C10—H10C	109.5
C3—C5—H5	120.1	C1—N1—C2	123.65 (12)
C5—C6—C7	119.60 (14)	C1—N1—N3	117.72 (12)
C5—C6—H6	120.2	C2—N1—N3	118.63 (13)
C7—C6—H6	120.2	C1—N2—C4	117.90 (12)
C8—C7—C6	121.48 (16)	N1—N3—H3A	110.0 (14)
C8—C7—H7	119.3	N1—N3—H3B	104.8 (18)
C6—C7—H7	119.3	H3A—N3—H3B	109 (2)
C7—C8—C4	119.78 (16)
O1—C2—C3—C4	−179.89 (12)	N2—C1—C9—C10	1.5 (2)
N1—C2—C3—C4	0.7 (2)	N1—C1—C9—C10	−179.13 (11)
O1—C2—C3—C5	0.4 (2)	N2—C1—N1—C2	0.9 (2)
N1—C2—C3—C5	−178.98 (10)	C9—C1—N1—C2	−178.40 (10)
C5—C3—C4—N2	−179.87 (11)	N2—C1—N1—N3	−178.35 (11)
C2—C3—C4—N2	0.4 (2)	C9—C1—N1—N3	2.30 (19)
C5—C3—C4—C8	0.0 (2)	O1—C2—N1—C1	179.18 (12)
C2—C3—C4—C8	−179.75 (11)	C3—C2—N1—C1	−1.4 (2)
C4—C3—C5—C6	−0.3 (2)	O1—C2—N1—N3	−1.5 (2)
C2—C3—C5—C6	179.44 (12)	C3—C2—N1—N3	177.87 (11)
C3—C5—C6—C7	0.4 (3)	N1—C1—N2—C4	0.3 (2)
C5—C6—C7—C8	−0.2 (3)	C9—C1—N2—C4	179.64 (10)
C6—C7—C8—C4	−0.1 (3)	C3—C4—N2—C1	−1.0 (2)
N2—C4—C8—C7	−179.95 (14)	C8—C4—N2—C1	179.19 (11)
C3—C4—C8—C7	0.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1i	0.91 (2)	2.12 (2)	2.974 (2)	157.1 (19)

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N3H3AO1i	0.91(2)	2.12(2)	2.974(2)	157.1(19)

Symmetry code: (i) .