Crystal structure of 4-methyl-sulfanyl-2-phenyl-quinazoline.

In the title compound, C15H12N2S, the methylthioquinazoline group is planar with the methyl C displaced by only 0.116 (3) Å from the plane of the quinazoline moiety. The dihedral angle between the phenyl ring and the quinazoline ring system is 13.95 (5)°. In the crystal, each molecule is linked by π-π stacking between to two adjacent inversion-related molecules. On one side, the inverted quinazoline groups interact with a centroid-centroid distance of 3.7105 (9) Å. On the other side, the quinazoline group interacts with the pyrimidine and phenyl rings of the second neighbour with centroid-centroid distances of 3.5287 (8) and 3.8601 (9) Å, respectively.

Related literature

For the synthesis of 4-alkythio­qinazolines, see: Leonard & Curtin (1946 ▶); Hearn et al. (1951 ▶); Meerwein et al. (1956 ▶); Blatter & Lukaszewski (1964 ▶); Segarra et al. (1998 ▶); Smith et al. (2005a ▶,b ▶).

Experimental

Crystal data

C15H12N2S

M = 252.33

Monoclinic,

a = 10.1951 (3) Å

b = 7.3545 (2) Å

c = 16.5300 (5) Å

β = 102.860 (3)°

V = 1208.33 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 150 K

0.23 × 0.18 × 0.15 mm

Data collection

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

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013 ▶) T min = 0.848, T max = 1.000

11140 measured reflections

3025 independent reflections

2558 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.097

S = 1.08

3025 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.34 e Å−3

Data collection: CrysAlis PRO (Agilent, 2013 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814015657/xu5801sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814015657/xu5801Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814015657/xu5801Isup3.cml

CCDC reference: 1012164

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

C15H12N2S	F(000) = 528
Mr = 252.33	Dx = 1.387 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.1951 (3) Å	Cell parameters from 2558 reflections
b = 7.3545 (2) Å	θ = 3.1–29.7°
c = 16.5300 (5) Å	µ = 0.25 mm−1
β = 102.860 (3)°	T = 150 K
V = 1208.33 (6) Å3	Block, colourless
Z = 4	0.23 × 0.18 × 0.15 mm

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer	3025 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2558 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.030
ω scans	θmax = 29.7°, θmin = 3.1°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	h = −13→12
Tmin = 0.848, Tmax = 1.000	k = −9→10
11140 measured reflections	l = −17→22

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039	H-atom parameters constrained
wR(F2) = 0.097	w = 1/[σ2(Fo2) + (0.0323P)2 + 0.6772P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
3025 reflections	Δρmax = 0.29 e Å−3
164 parameters	Δρmin = −0.34 e Å−3

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	0.09137 (15)	0.6738 (2)	−0.06125 (9)	0.0182 (3)
C2	0.06916 (15)	0.7676 (2)	0.06700 (9)	0.0189 (3)
C3	−0.07074 (14)	0.8041 (2)	0.03446 (9)	0.0183 (3)
C4	−0.11800 (15)	0.7663 (2)	−0.05066 (9)	0.0196 (3)
C5	−0.16032 (16)	0.8695 (2)	0.08196 (10)	0.0229 (3)
H5	−0.1285	0.8950	0.1393	0.027*
C6	−0.29284 (16)	0.8957 (2)	0.04503 (10)	0.0257 (3)
H6	−0.3531	0.9391	0.0770	0.031*
C7	−0.34049 (16)	0.8591 (2)	−0.03973 (11)	0.0266 (4)
H7	−0.4328	0.8783	−0.0646	0.032*
C8	−0.25564 (15)	0.7960 (2)	−0.08710 (10)	0.0246 (3)
H8	−0.2892	0.7723	−0.1445	0.030*
C9	0.18424 (15)	0.5989 (2)	−0.11089 (9)	0.0188 (3)
C10	0.13360 (15)	0.5219 (2)	−0.18889 (9)	0.0213 (3)
H10	0.0394	0.5222	−0.2116	0.026*
C11	0.22001 (16)	0.4449 (2)	−0.23338 (9)	0.0237 (3)
H11	0.1846	0.3913	−0.2860	0.028*
C12	0.35767 (16)	0.4460 (2)	−0.20139 (10)	0.0253 (3)
H12	0.4166	0.3939	−0.2321	0.030*
C13	0.40914 (16)	0.5234 (2)	−0.12434 (10)	0.0250 (3)
H13	0.5036	0.5249	−0.1025	0.030*
C14	0.32309 (15)	0.5986 (2)	−0.07900 (9)	0.0225 (3)
H14	0.3589	0.6502	−0.0260	0.027*
C15	0.30675 (16)	0.7320 (3)	0.18247 (10)	0.0289 (4)
H15A	0.3070	0.6036	0.1666	0.043*
H15B	0.3564	0.7464	0.2401	0.043*
H15C	0.3498	0.8048	0.1460	0.043*
N1	0.14809 (12)	0.70406 (17)	0.02073 (8)	0.0191 (3)
N2	−0.03494 (12)	0.70111 (17)	−0.09896 (8)	0.0200 (3)
S1	0.13627 (4)	0.80726 (6)	0.17278 (2)	0.02388 (12)

	U11	U22	U33	U12	U13	U23
C1	0.0219 (7)	0.0154 (7)	0.0174 (7)	−0.0014 (5)	0.0049 (6)	0.0015 (6)
C2	0.0237 (7)	0.0172 (7)	0.0156 (7)	−0.0014 (6)	0.0042 (6)	0.0017 (6)
C3	0.0216 (7)	0.0147 (7)	0.0191 (7)	−0.0010 (5)	0.0058 (6)	0.0020 (6)
C4	0.0218 (7)	0.0173 (7)	0.0202 (7)	−0.0011 (6)	0.0055 (6)	0.0014 (6)
C5	0.0282 (8)	0.0212 (8)	0.0208 (8)	0.0013 (6)	0.0088 (6)	0.0005 (6)
C6	0.0254 (8)	0.0229 (8)	0.0316 (9)	0.0035 (6)	0.0126 (7)	−0.0004 (7)
C7	0.0195 (7)	0.0261 (8)	0.0335 (9)	0.0018 (6)	0.0043 (6)	0.0005 (7)
C8	0.0222 (8)	0.0274 (9)	0.0231 (8)	−0.0008 (6)	0.0024 (6)	−0.0016 (7)
C9	0.0232 (7)	0.0161 (7)	0.0176 (7)	0.0008 (6)	0.0059 (6)	0.0026 (6)
C10	0.0229 (7)	0.0216 (8)	0.0195 (7)	−0.0004 (6)	0.0048 (6)	0.0022 (6)
C11	0.0318 (8)	0.0225 (8)	0.0174 (7)	−0.0004 (6)	0.0067 (6)	−0.0011 (6)
C12	0.0300 (8)	0.0234 (8)	0.0256 (8)	0.0037 (6)	0.0131 (7)	0.0006 (7)
C13	0.0226 (8)	0.0258 (9)	0.0274 (8)	0.0019 (6)	0.0071 (6)	0.0017 (7)
C14	0.0252 (8)	0.0230 (8)	0.0188 (7)	0.0001 (6)	0.0039 (6)	−0.0002 (6)
C15	0.0241 (8)	0.0406 (10)	0.0202 (8)	0.0037 (7)	0.0011 (6)	0.0014 (7)
N1	0.0209 (6)	0.0198 (6)	0.0171 (6)	−0.0007 (5)	0.0050 (5)	0.0019 (5)
N2	0.0218 (6)	0.0200 (6)	0.0185 (6)	−0.0005 (5)	0.0051 (5)	−0.0009 (5)
S1	0.0248 (2)	0.0308 (2)	0.0159 (2)	0.00122 (15)	0.00423 (15)	−0.00238 (16)

C1—N2	1.3153 (19)	C8—H8	0.9500
C1—N1	1.3680 (19)	C9—C14	1.396 (2)
C1—C9	1.4897 (19)	C9—C10	1.398 (2)
C2—N1	1.3134 (18)	C10—C11	1.388 (2)
C2—C3	1.433 (2)	C10—H10	0.9500
C2—S1	1.7544 (15)	C11—C12	1.385 (2)
C3—C4	1.410 (2)	C11—H11	0.9500
C3—C5	1.414 (2)	C12—C13	1.387 (2)
C4—N2	1.3730 (18)	C12—H12	0.9500
C4—C8	1.415 (2)	C13—C14	1.389 (2)
C5—C6	1.367 (2)	C13—H13	0.9500
C5—H5	0.9500	C14—H14	0.9500
C6—C7	1.403 (2)	C15—S1	1.7970 (16)
C6—H6	0.9500	C15—H15A	0.9800
C7—C8	1.370 (2)	C15—H15B	0.9800
C7—H7	0.9500	C15—H15C	0.9800
N2—C1—N1	126.73 (13)	C10—C9—C1	120.56 (13)
N2—C1—C9	118.08 (13)	C11—C10—C9	120.43 (14)
N1—C1—C9	115.18 (13)	C11—C10—H10	119.8
N1—C2—C3	122.39 (13)	C9—C10—H10	119.8
N1—C2—S1	119.07 (11)	C12—C11—C10	120.27 (15)
C3—C2—S1	118.54 (11)	C12—C11—H11	119.9
C4—C3—C5	120.11 (14)	C10—C11—H11	119.9
C4—C3—C2	115.34 (13)	C11—C12—C13	119.80 (14)
C5—C3—C2	124.53 (14)	C11—C12—H12	120.1
N2—C4—C3	122.09 (13)	C13—C12—H12	120.1
N2—C4—C8	119.20 (14)	C12—C13—C14	120.23 (15)
C3—C4—C8	118.71 (13)	C12—C13—H13	119.9
C6—C5—C3	119.75 (15)	C14—C13—H13	119.9
C6—C5—H5	120.1	C13—C14—C9	120.38 (14)
C3—C5—H5	120.1	C13—C14—H14	119.8
C5—C6—C7	120.47 (14)	C9—C14—H14	119.8
C5—C6—H6	119.8	S1—C15—H15A	109.5
C7—C6—H6	119.8	S1—C15—H15B	109.5
C8—C7—C6	120.88 (15)	H15A—C15—H15B	109.5
C8—C7—H7	119.6	S1—C15—H15C	109.5
C6—C7—H7	119.6	H15A—C15—H15C	109.5
C7—C8—C4	120.08 (15)	H15B—C15—H15C	109.5
C7—C8—H8	120.0	C2—N1—C1	117.13 (13)
C4—C8—H8	120.0	C1—N2—C4	116.31 (13)
C14—C9—C10	118.88 (13)	C2—S1—C15	101.10 (7)
C14—C9—C1	120.52 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15B···N2i	0.98	2.67	3.648 (2)	173