Crystal structure of 4-meth-oxy-quinazoline.

The title compound, C9H8N2O, is almost planar, with the C atom of the meth-oxy group deviating from the mean plane of the quinazoline ring system (r.m.s. deviation = 0.011 Å) by 0.068 (4) Å. In the crystal, mol-ecules form π-π stacks parallel to the b-axis direction [centroid-centroid separation = 3.5140 (18) Å], leading to a herringbone packing arrangement.

Related literature

For the synthesis of quinazoline derivatives, see: Bogert & May (1909 ▶); Smith et al. (2005 ▶); Wang et al. (2010 ▶); Yang et al. (2010 ▶); Han et al. (2012 ▶). For the crystal structures of related compounds, see Alshammari et al. (2014 ▶); Derabli et al. (2013 ▶); Gao et al. (2012 ▶); Huang & Tan (2012 ▶); Jia et al. (2011 ▶).

Experimental

Crystal data

C9H8N2O

M = 160.17

Monoclinic,

a = 6.9590 (6) Å

b = 4.0517 (3) Å

c = 13.5858 (12) Å

β = 91.754 (8)°

V = 382.88 (6) Å3

Z = 2

Cu Kα radiation

μ = 0.77 mm−1

T = 150 K

0.57 × 0.12 × 0.08 mm

Data collection

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer

Absorption correction: gaussian (CrysAlis PRO; Agilent, 2014 ▶) T min = 0.641, T max = 0.895

2166 measured reflections

1435 independent reflections

1311 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.159

S = 1.08

1435 reflections

110 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.23 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, 2008 ▶); 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/S1600536814025082/hb7317sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814025082/hb7317Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814025082/hb7317Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814025082/hb7317fig1.tif

The title mol­ecule showing 50% probability displacement ellipsoids.

Click here for additional data file.

a . DOI: 10.1107/S1600536814025082/hb7317fig2.tif

Crystal packing viewed down the a axis.

CCDC reference: 1034363

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

C9H8N2O	F(000) = 168
Mr = 160.17	Dx = 1.389 Mg m−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54184 Å
a = 6.9590 (6) Å	Cell parameters from 1311 reflections
b = 4.0517 (3) Å	θ = 3.3–67.7°
c = 13.5858 (12) Å	µ = 0.77 mm−1
β = 91.754 (8)°	T = 150 K
V = 382.88 (6) Å3	Needle, colourless
Z = 2	0.57 × 0.12 × 0.08 mm

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer	1311 reflections with I > 2σ(I)
ω scans	Rint = 0.040
Absorption correction: gaussian (CrysAlis PRO; Agilent, 2014)	θmax = 74.6°, θmin = 3.3°
Tmin = 0.641, Tmax = 0.895	h = −8→8
2166 measured reflections	k = −4→5
1435 independent reflections	l = −11→16

Refinement on F2	1 restraint
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.054	H-atom parameters constrained
wR(F2) = 0.159	w = 1/[σ2(Fo2) + (0.110P)2 + 0.0483P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
1435 reflections	Δρmax = 0.24 e Å−3
110 parameters	Δρmin = −0.23 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	−0.1179 (5)	0.8736 (9)	0.7198 (2)	0.0403 (8)
H1	−0.2391	0.7831	0.7078	0.048*
C2	0.1829 (4)	0.9515 (7)	0.6650 (2)	0.0330 (7)
C3	0.2338 (4)	1.1283 (7)	0.7527 (2)	0.0330 (7)
C4	0.0855 (4)	1.1608 (7)	0.8208 (2)	0.0349 (7)
C5	0.1265 (5)	1.3290 (8)	0.9096 (3)	0.0426 (8)
H5	0.0308	1.3526	0.9554	0.051*
C6	0.3034 (5)	1.4570 (8)	0.9292 (2)	0.0431 (8)
H6	0.3276	1.5675	0.9883	0.052*
C7	0.4520 (5)	1.4246 (10)	0.8608 (3)	0.0411 (7)
H7	0.5731	1.5127	0.8751	0.049*
C8	0.4169 (5)	1.2640 (7)	0.7739 (2)	0.0364 (7)
H8	0.5138	1.2440	0.7287	0.044*
C9	0.2674 (5)	0.7530 (9)	0.5079 (3)	0.0433 (8)
H9A	0.1669	0.8757	0.4745	0.065*
H9B	0.2226	0.5340	0.5215	0.065*
H9C	0.3771	0.7410	0.4669	0.065*
N1	−0.0945 (4)	1.0312 (7)	0.8028 (2)	0.0412 (7)
N2	0.0121 (4)	0.8237 (6)	0.6479 (2)	0.0378 (7)
O1	0.3208 (3)	0.9159 (6)	0.59930 (16)	0.0381 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0293 (13)	0.0351 (16)	0.0562 (19)	−0.0019 (13)	−0.0033 (12)	0.0037 (15)
C2	0.0334 (14)	0.0278 (15)	0.0374 (15)	0.0007 (13)	−0.0059 (11)	0.0054 (12)
C3	0.0310 (14)	0.0268 (14)	0.0408 (15)	0.0051 (11)	−0.0036 (12)	0.0073 (12)
C4	0.0356 (16)	0.0283 (15)	0.0405 (16)	0.0033 (13)	−0.0020 (12)	0.0071 (13)
C5	0.0473 (18)	0.0386 (17)	0.0423 (18)	0.0053 (15)	0.0052 (14)	0.0023 (15)
C6	0.0528 (19)	0.0364 (18)	0.0396 (17)	0.0030 (15)	−0.0075 (14)	−0.0008 (14)
C7	0.0367 (14)	0.0373 (16)	0.0486 (17)	0.0006 (14)	−0.0104 (12)	0.0020 (14)
C8	0.0327 (14)	0.0346 (16)	0.0416 (18)	0.0033 (13)	−0.0051 (12)	0.0057 (14)
C9	0.0445 (17)	0.0437 (18)	0.0414 (17)	0.0051 (16)	−0.0052 (13)	−0.0020 (14)
N1	0.0336 (13)	0.0372 (14)	0.0528 (17)	−0.0001 (11)	0.0023 (11)	0.0013 (13)
N2	0.0346 (13)	0.0336 (14)	0.0446 (14)	−0.0001 (10)	−0.0084 (11)	0.0044 (11)
O1	0.0346 (10)	0.0430 (13)	0.0367 (11)	−0.0004 (11)	−0.0016 (8)	−0.0004 (10)

C1—N1	1.302 (4)	C5—H5	0.9300
C1—N2	1.366 (4)	C6—C7	1.417 (5)
C1—H1	0.9300	C6—H6	0.9300
C2—N2	1.311 (4)	C7—C8	1.363 (5)
C2—O1	1.338 (4)	C7—H7	0.9300
C2—C3	1.425 (4)	C8—H8	0.9300
C3—C8	1.409 (4)	C9—O1	1.445 (4)
C3—C4	1.413 (4)	C9—H9A	0.9600
C4—N1	1.373 (4)	C9—H9B	0.9600
C4—C5	1.407 (5)	C9—H9C	0.9600
C5—C6	1.355 (5)
N1—C1—N2	128.6 (3)	C7—C6—H6	119.6
N1—C1—H1	115.7	C8—C7—C6	119.8 (3)
N2—C1—H1	115.7	C8—C7—H7	120.1
N2—C2—O1	120.3 (3)	C6—C7—H7	120.1
N2—C2—C3	123.2 (3)	C7—C8—C3	120.0 (3)
O1—C2—C3	116.5 (2)	C7—C8—H8	120.0
C8—C3—C4	120.2 (3)	C3—C8—H8	120.0
C8—C3—C2	124.6 (3)	O1—C9—H9A	109.5
C4—C3—C2	115.2 (3)	O1—C9—H9B	109.5
N1—C4—C5	119.8 (3)	H9A—C9—H9B	109.5
N1—C4—C3	121.9 (3)	O1—C9—H9C	109.5
C5—C4—C3	118.2 (3)	H9A—C9—H9C	109.5
C6—C5—C4	120.9 (3)	H9B—C9—H9C	109.5
C6—C5—H5	119.6	C1—N1—C4	115.5 (3)
C4—C5—H5	119.6	C2—N2—C1	115.6 (3)
C5—C6—C7	120.8 (3)	C2—O1—C9	116.9 (2)
C5—C6—H6	119.6