Crystal structure of 2-ethyl-quinazoline-4(3H)-thione.

In the title compound, C10H10N2S, all non-H atoms are almost coplanar [maximum deviation = 0.103 (1) Å]. In the crystal, N-H⋯S inter-actions form R 2 (2)(8) rings linking pairs of mol-ecules related by inversion. The mol-ecular pairs are stacked along [100]. A herringbone arrangement of pairs in the [010] direction forms layers parallel to (010).

Related literature

For the synthesis of quinazoline-4(3H)-thio­nes, see: Bogert et al. (1903 ▶); Zoltewicz & Sharpless (1976 ▶); Segarra et al. (1998 ▶); El-Hiti (2004 ▶); Ozturk et al. (2007 ▶); El-Hiti et al. (2011 ▶).

Experimental

Crystal data

C10H10N2S

M = 190.26

Orthorhombic,

a = 5.8231 (3) Å

b = 14.3214 (6) Å

c = 21.7365 (8) Å

V = 1812.71 (14) Å3

Z = 8

Mo Kα radiation

μ = 0.31 mm−1

T = 150 K

0.41 × 0.24 × 0.15 mm

Data collection

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

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014 ▶) T min = 0.780, T max = 1.000

7795 measured reflections

2240 independent reflections

1973 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.087

S = 1.03

2240 reflections

119 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrysAlis PRO (Agilent, 2014 ▶); 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/S160053681401664X/xu5804sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681401664X/xu5804Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S160053681401664X/xu5804Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S160053681401664X/xu5804fig1.tif

A mol­ecule of the title compound showing atom labels and 50% probability displacement ellipsoids for non-H atoms.

Click here for additional data file.

. DOI: 10.1107/S160053681401664X/xu5804fig2.tif

Crystal structure packing showing N—H⋯S contacts as dotted lines.

CCDC reference: 1014729

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

C10H10N2S	Dx = 1.394 Mg m−3
Mr = 190.26	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 3617 reflections
a = 5.8231 (3) Å	θ = 3.9–29.3°
b = 14.3214 (6) Å	µ = 0.31 mm−1
c = 21.7365 (8) Å	T = 150 K
V = 1812.71 (14) Å3	Plate, yellow
Z = 8	0.41 × 0.24 × 0.15 mm
F(000) = 800

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer	2240 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1973 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.020
ω scans	θmax = 29.8°, θmin = 3.0°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	h = −6→7
Tmin = 0.780, Tmax = 1.000	k = −19→14
7795 measured reflections	l = −23→29

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033	H-atom parameters constrained
wR(F2) = 0.087	w = 1/[σ2(Fo2) + (0.0416P)2 + 0.7981P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
2240 reflections	Δρmax = 0.30 e Å−3
119 parameters	Δρmin = −0.25 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	0.7433 (2)	0.57478 (9)	0.62537 (6)	0.0185 (3)
C2	0.6649 (2)	0.44643 (8)	0.55604 (5)	0.0178 (2)
C3	0.4705 (2)	0.42557 (8)	0.59550 (5)	0.0177 (3)
C4	0.4368 (2)	0.48131 (8)	0.64832 (5)	0.0183 (3)
C5	0.3171 (2)	0.35262 (9)	0.58239 (6)	0.0209 (3)
H5	0.3379	0.3158	0.5465	0.025*
C6	0.1366 (2)	0.33425 (9)	0.62146 (6)	0.0236 (3)
H6	0.0337	0.2845	0.6127	0.028*
C7	0.1046 (2)	0.38917 (9)	0.67440 (6)	0.0240 (3)
H7	−0.0197	0.3760	0.7013	0.029*
C8	0.2513 (2)	0.46175 (9)	0.68761 (6)	0.0218 (3)
H8	0.2272	0.4987	0.7233	0.026*
C9	0.8998 (2)	0.65696 (9)	0.63452 (6)	0.0227 (3)
H9A	0.8734	0.7023	0.6009	0.027*
H9B	1.0609	0.6354	0.6316	0.027*
C10	0.8668 (3)	0.70632 (9)	0.69567 (6)	0.0246 (3)
H10A	0.7058	0.7252	0.7000	0.037*
H10B	0.9652	0.7618	0.6972	0.037*
H10C	0.9080	0.6639	0.7293	0.037*
N1	0.78973 (18)	0.52156 (7)	0.57402 (5)	0.0188 (2)
H1	0.9086	0.5374	0.5513	0.023*
N2	0.57662 (19)	0.55697 (7)	0.66273 (5)	0.0199 (2)
S1	0.73978 (6)	0.38502 (2)	0.49367 (2)	0.02214 (11)

	U11	U22	U33	U12	U13	U23
C1	0.0210 (6)	0.0177 (6)	0.0169 (6)	0.0022 (5)	−0.0006 (4)	−0.0010 (5)
C2	0.0203 (6)	0.0164 (5)	0.0166 (5)	0.0039 (5)	−0.0026 (5)	0.0008 (4)
C3	0.0194 (6)	0.0171 (6)	0.0167 (5)	0.0027 (5)	−0.0019 (5)	0.0020 (4)
C4	0.0197 (6)	0.0178 (6)	0.0172 (5)	0.0019 (5)	−0.0012 (4)	0.0010 (5)
C5	0.0237 (7)	0.0189 (6)	0.0202 (6)	0.0008 (5)	−0.0032 (5)	−0.0006 (5)
C6	0.0238 (7)	0.0212 (6)	0.0258 (6)	−0.0033 (5)	−0.0029 (5)	0.0012 (5)
C7	0.0213 (7)	0.0264 (7)	0.0244 (6)	−0.0013 (5)	0.0028 (5)	0.0038 (5)
C8	0.0242 (7)	0.0226 (6)	0.0186 (6)	0.0015 (5)	0.0016 (5)	0.0002 (5)
C9	0.0238 (7)	0.0208 (6)	0.0233 (6)	−0.0033 (5)	0.0041 (5)	−0.0040 (5)
C10	0.0292 (7)	0.0233 (6)	0.0214 (6)	−0.0047 (5)	0.0001 (5)	−0.0040 (5)
N1	0.0188 (5)	0.0194 (5)	0.0182 (5)	−0.0003 (4)	0.0030 (4)	−0.0024 (4)
N2	0.0220 (6)	0.0191 (5)	0.0187 (5)	−0.0006 (4)	0.0015 (4)	−0.0012 (4)
S1	0.0244 (2)	0.02191 (18)	0.02011 (17)	0.00029 (12)	0.00293 (12)	−0.00599 (12)

C1—N2	1.2908 (16)	C6—C7	1.4061 (19)
C1—N1	1.3784 (16)	C6—H6	0.9500
C1—C9	1.5017 (18)	C7—C8	1.3757 (19)
C2—N1	1.3560 (16)	C7—H7	0.9500
C2—C3	1.4514 (17)	C8—H8	0.9500
C2—S1	1.6737 (12)	C9—C10	1.5177 (17)
C3—C5	1.4038 (18)	C9—H9A	0.9900
C3—C4	1.4119 (16)	C9—H9B	0.9900
C4—N2	1.3910 (16)	C10—H10A	0.9800
C4—C8	1.4054 (18)	C10—H10B	0.9800
C5—C6	1.3766 (19)	C10—H10C	0.9800
C5—H5	0.9500	N1—H1	0.8800
N2—C1—N1	123.21 (12)	C6—C7—H7	119.6
N2—C1—C9	121.86 (11)	C7—C8—C4	120.08 (12)
N1—C1—C9	114.92 (11)	C7—C8—H8	120.0
N1—C2—C3	114.27 (11)	C4—C8—H8	120.0
N1—C2—S1	120.71 (10)	C1—C9—C10	113.84 (11)
C3—C2—S1	125.01 (10)	C1—C9—H9A	108.8
C5—C3—C4	119.83 (12)	C10—C9—H9A	108.8
C5—C3—C2	121.97 (11)	C1—C9—H9B	108.8
C4—C3—C2	118.19 (11)	C10—C9—H9B	108.8
N2—C4—C8	117.93 (11)	H9A—C9—H9B	107.7
N2—C4—C3	122.83 (11)	C9—C10—H10A	109.5
C8—C4—C3	119.22 (12)	C9—C10—H10B	109.5
C6—C5—C3	120.19 (12)	H10A—C10—H10B	109.5
C6—C5—H5	119.9	C9—C10—H10C	109.5
C3—C5—H5	119.9	H10A—C10—H10C	109.5
C5—C6—C7	119.94 (12)	H10B—C10—H10C	109.5
C5—C6—H6	120.0	C2—N1—C1	124.53 (11)
C7—C6—H6	120.0	C2—N1—H1	117.7
C8—C7—C6	120.73 (13)	C1—N1—H1	117.7
C8—C7—H7	119.6	C1—N2—C4	116.89 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1i	0.88	2.53	3.3854 (11)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S1i	0.88	2.53	3.3854 (11)	166

Symmetry code: (i) .