3-Benzyl-6-methyl-2-sulfanylidene-2,3-di-hydroquinazolin-4(1H)-one.

In the title compound, C(16)H(14)N(2)OS, the quinazoline ring system is essentially planar, with a maximum deviation of 0.029 (3) Å. The dihedral angle between the quinazoline and benzene rings is 88.4 (2)°. In the crystal, adjacent mol-ecules are connected via pairs of N-H⋯S and C-H⋯O hydrogen bonds, which generate R(2) (2)(8) and R(2) (2)(10) graph-set motifs, respectively, resulting in a supra-molecular chain along the a axis.

Related literature

For details and applications of quinazoline compounds, see: Roth & Fenner (2000 ▶); Jantova et al. (2004 ▶); Harris & Thorarensen (2004 ▶); Andries et al. (2005 ▶); Al-Rashood et al. (2006 ▶); Ghorab et al. (2007 ▶); Rádl et al. (2000 ▶); Klepser & Klepser (1997 ▶); Al-Omar et al. (2004 ▶); Al-Omary et al. (2010 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H14N2OS

M = 282.35

Monoclinic,

a = 24.2438 (18) Å

b = 5.1618 (5) Å

c = 24.4265 (17) Å

β = 111.532 (6)°

V = 2843.4 (4) Å3

Z = 8

Cu Kα radiation

μ = 1.99 mm−1

T = 296 K

0.83 × 0.12 × 0.06 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.289, T max = 0.890

9528 measured reflections

2592 independent reflections

1421 reflections with I > 2σ(I)

R int = 0.104

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.166

S = 0.93

2592 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812006009/is5070sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812006009/is5070Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812006009/is5070Isup3.cml

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

C16H14N2OS	F(000) = 1184
Mr = 282.35	Dx = 1.319 Mg m−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -C 2yc	Cell parameters from 339 reflections
a = 24.2438 (18) Å	θ = 3.9–53.5°
b = 5.1618 (5) Å	µ = 1.99 mm−1
c = 24.4265 (17) Å	T = 296 K
β = 111.532 (6)°	Needle, colourless
V = 2843.4 (4) Å3	0.83 × 0.12 × 0.06 mm
Z = 8

Bruker SMART APEXII CCD diffractometer	2592 independent reflections
Radiation source: fine-focus sealed tube	1421 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.104
φ and ω scans	θmax = 69.8°, θmin = 3.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −29→29
Tmin = 0.289, Tmax = 0.890	k = −6→5
9528 measured reflections	l = −28→28

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.166	H-atom parameters constrained
S = 0.93	w = 1/[σ2(Fo2) + (0.0875P)2] where P = (Fo2 + 2Fc2)/3
2592 reflections	(Δ/σ)max = 0.001
182 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
S1	0.22029 (4)	0.1447 (2)	0.07055 (4)	0.0718 (3)
N1	0.17921 (10)	0.4985 (6)	−0.01167 (11)	0.0630 (7)
H1A	0.2097	0.4590	−0.0199	0.076*
N2	0.12318 (10)	0.4401 (5)	0.04598 (11)	0.0574 (7)
O1	0.04534 (10)	0.7057 (5)	0.03541 (11)	0.0747 (7)
C1	0.17206 (13)	0.3706 (7)	0.03308 (14)	0.0594 (8)
C2	0.08423 (13)	0.6424 (7)	0.01808 (14)	0.0600 (8)
C3	0.09395 (12)	0.7664 (7)	−0.03127 (13)	0.0585 (8)
C4	0.05611 (13)	0.9575 (7)	−0.06444 (14)	0.0630 (9)
H4A	0.0243	1.0100	−0.0544	0.076*
C5	0.06438 (15)	1.0717 (7)	−0.11196 (15)	0.0691 (9)
C6	0.11382 (16)	0.9891 (8)	−0.12434 (16)	0.0763 (10)
H6A	0.1206	1.0638	−0.1559	0.092*
C7	0.15210 (15)	0.8048 (7)	−0.09221 (15)	0.0715 (10)
H7A	0.1848	0.7578	−0.1013	0.086*
C8	0.14201 (13)	0.6879 (7)	−0.04573 (14)	0.0578 (8)
C9	0.10920 (14)	0.2997 (7)	0.09172 (15)	0.0657 (9)
H9A	0.1263	0.1276	0.0958	0.079*
H9B	0.0665	0.2799	0.0788	0.079*
C10	0.13111 (14)	0.4281 (7)	0.15093 (14)	0.0641 (9)
C11	0.1103 (2)	0.3376 (10)	0.1930 (2)	0.0988 (15)
H11A	0.0831	0.2022	0.1840	0.119*
C12	0.1298 (3)	0.4483 (15)	0.2483 (2)	0.131 (2)
H12A	0.1144	0.3902	0.2758	0.157*
C13	0.1710 (3)	0.6401 (16)	0.2634 (2)	0.133 (2)
H13A	0.1854	0.7057	0.3015	0.160*
C14	0.1912 (2)	0.7364 (11)	0.2216 (2)	0.1082 (15)
H14A	0.2179	0.8737	0.2306	0.130*
C15	0.17129 (17)	0.6268 (8)	0.16567 (16)	0.0783 (11)
H15A	0.1856	0.6898	0.1377	0.094*
C16	0.02217 (18)	1.2711 (9)	−0.14931 (18)	0.0893 (12)
H16B	−0.0064	1.3143	−0.1321	0.134*
H16A	0.0021	1.2027	−0.1881	0.134*
H16C	0.0438	1.4238	−0.1516	0.134*

	U11	U22	U33	U12	U13	U23
S1	0.0640 (5)	0.0875 (7)	0.0707 (6)	0.0172 (4)	0.0327 (5)	0.0084 (5)
N1	0.0558 (14)	0.083 (2)	0.0576 (17)	0.0153 (13)	0.0295 (14)	0.0029 (15)
N2	0.0510 (13)	0.0688 (18)	0.0577 (16)	0.0036 (11)	0.0264 (13)	−0.0049 (13)
O1	0.0601 (12)	0.0924 (19)	0.0855 (17)	0.0135 (11)	0.0430 (13)	−0.0007 (13)
C1	0.0500 (16)	0.076 (2)	0.0554 (19)	0.0024 (14)	0.0231 (16)	−0.0121 (17)
C2	0.0498 (16)	0.073 (2)	0.059 (2)	0.0022 (14)	0.0228 (16)	−0.0124 (17)
C3	0.0472 (16)	0.076 (2)	0.051 (2)	−0.0010 (14)	0.0169 (16)	−0.0104 (17)
C4	0.0543 (17)	0.070 (2)	0.066 (2)	0.0069 (15)	0.0225 (17)	−0.0068 (18)
C5	0.065 (2)	0.074 (2)	0.066 (2)	0.0057 (16)	0.0211 (18)	−0.0006 (19)
C6	0.077 (2)	0.086 (3)	0.072 (2)	0.0089 (18)	0.035 (2)	0.008 (2)
C7	0.068 (2)	0.090 (3)	0.068 (2)	0.0134 (17)	0.0375 (19)	0.009 (2)
C8	0.0472 (16)	0.073 (2)	0.0540 (19)	0.0062 (13)	0.0194 (15)	−0.0060 (16)
C9	0.0629 (19)	0.065 (2)	0.080 (2)	−0.0013 (14)	0.0393 (19)	−0.0001 (18)
C10	0.0643 (18)	0.074 (2)	0.063 (2)	0.0196 (16)	0.0343 (18)	0.0090 (18)
C11	0.115 (3)	0.114 (4)	0.090 (3)	0.020 (3)	0.065 (3)	0.028 (3)
C12	0.150 (6)	0.185 (7)	0.080 (4)	0.064 (5)	0.069 (4)	0.043 (4)
C13	0.131 (5)	0.196 (7)	0.068 (3)	0.061 (4)	0.031 (4)	−0.018 (4)
C14	0.108 (4)	0.117 (4)	0.092 (3)	0.010 (3)	0.027 (3)	−0.030 (3)
C15	0.082 (2)	0.089 (3)	0.066 (3)	0.002 (2)	0.029 (2)	−0.011 (2)
C16	0.082 (3)	0.091 (3)	0.092 (3)	0.014 (2)	0.028 (2)	0.012 (2)

S1—C1	1.667 (3)	C7—H7A	0.9300
N1—C1	1.342 (4)	C9—C10	1.500 (5)
N1—C8	1.382 (4)	C9—H9A	0.9700
N1—H1A	0.8600	C9—H9B	0.9700
N2—C1	1.381 (3)	C10—C15	1.369 (5)
N2—C2	1.405 (4)	C10—C11	1.381 (5)
N2—C9	1.472 (4)	C11—C12	1.382 (7)
O1—C2	1.212 (3)	C11—H11A	0.9300
C2—C3	1.458 (4)	C12—C13	1.357 (9)
C3—C4	1.388 (5)	C12—H12A	0.9300
C3—C8	1.396 (4)	C13—C14	1.377 (8)
C4—C5	1.381 (5)	C13—H13A	0.9300
C4—H4A	0.9300	C14—C15	1.390 (6)
C5—C6	1.406 (5)	C14—H14A	0.9300
C5—C16	1.501 (5)	C15—H15A	0.9300
C6—C7	1.359 (5)	C16—H16B	0.9600
C6—H6A	0.9300	C16—H16A	0.9600
C7—C8	1.385 (4)	C16—H16C	0.9600
C1—N1—C8	126.0 (2)	N2—C9—C10	114.6 (3)
C1—N1—H1A	117.0	N2—C9—H9A	108.6
C8—N1—H1A	117.0	C10—C9—H9A	108.6
C1—N2—C2	124.2 (3)	N2—C9—H9B	108.6
C1—N2—C9	120.1 (3)	C10—C9—H9B	108.6
C2—N2—C9	115.7 (2)	H9A—C9—H9B	107.6
N1—C1—N2	115.9 (3)	C15—C10—C11	118.5 (4)
N1—C1—S1	121.1 (2)	C15—C10—C9	123.4 (3)
N2—C1—S1	123.0 (2)	C11—C10—C9	118.1 (4)
O1—C2—N2	120.1 (3)	C10—C11—C12	120.0 (5)
O1—C2—C3	123.6 (3)	C10—C11—H11A	120.0
N2—C2—C3	116.3 (2)	C12—C11—H11A	120.0
C4—C3—C8	119.5 (3)	C13—C12—C11	121.3 (5)
C4—C3—C2	121.5 (3)	C13—C12—H12A	119.3
C8—C3—C2	119.0 (3)	C11—C12—H12A	119.3
C5—C4—C3	121.7 (3)	C12—C13—C14	119.3 (5)
C5—C4—H4A	119.1	C12—C13—H13A	120.4
C3—C4—H4A	119.1	C14—C13—H13A	120.4
C4—C5—C6	116.7 (3)	C13—C14—C15	119.5 (6)
C4—C5—C16	121.8 (3)	C13—C14—H14A	120.3
C6—C5—C16	121.5 (3)	C15—C14—H14A	120.3
C7—C6—C5	122.9 (3)	C10—C15—C14	121.3 (4)
C7—C6—H6A	118.5	C10—C15—H15A	119.3
C5—C6—H6A	118.5	C14—C15—H15A	119.3
C6—C7—C8	119.3 (3)	C5—C16—H16B	109.5
C6—C7—H7A	120.3	C5—C16—H16A	109.5
C8—C7—H7A	120.3	H16B—C16—H16A	109.5
N1—C8—C7	122.0 (3)	C5—C16—H16C	109.5
N1—C8—C3	118.3 (3)	H16B—C16—H16C	109.5
C7—C8—C3	119.7 (3)	H16A—C16—H16C	109.5
C8—N1—C1—N2	−0.9 (5)	C1—N1—C8—C7	−178.2 (3)
C8—N1—C1—S1	179.7 (3)	C1—N1—C8—C3	3.6 (5)
C2—N2—C1—N1	−4.2 (5)	C6—C7—C8—N1	179.7 (4)
C9—N2—C1—N1	176.0 (3)	C6—C7—C8—C3	−2.1 (6)
C2—N2—C1—S1	175.1 (2)	C4—C3—C8—N1	179.5 (3)
C9—N2—C1—S1	−4.6 (4)	C2—C3—C8—N1	−1.3 (5)
C1—N2—C2—O1	−173.6 (3)	C4—C3—C8—C7	1.3 (5)
C9—N2—C2—O1	6.1 (5)	C2—C3—C8—C7	−179.6 (3)
C1—N2—C2—C3	6.2 (5)	C1—N2—C9—C10	97.0 (3)
C9—N2—C2—C3	−174.1 (3)	C2—N2—C9—C10	−82.7 (3)
O1—C2—C3—C4	−4.2 (5)	N2—C9—C10—C15	−13.4 (5)
N2—C2—C3—C4	176.0 (3)	N2—C9—C10—C11	167.7 (3)
O1—C2—C3—C8	176.6 (3)	C15—C10—C11—C12	0.3 (6)
N2—C2—C3—C8	−3.1 (5)	C9—C10—C11—C12	179.3 (4)
C8—C3—C4—C5	0.5 (5)	C10—C11—C12—C13	−2.3 (8)
C2—C3—C4—C5	−178.6 (3)	C11—C12—C13—C14	3.8 (10)
C3—C4—C5—C6	−1.4 (5)	C12—C13—C14—C15	−3.2 (8)
C3—C4—C5—C16	177.6 (3)	C11—C10—C15—C14	0.2 (6)
C4—C5—C6—C7	0.5 (6)	C9—C10—C15—C14	−178.7 (4)
C16—C5—C6—C7	−178.5 (4)	C13—C14—C15—C10	1.3 (7)
C5—C6—C7—C8	1.3 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···S1i	0.86	2.50	3.335 (3)	165
C4—H4A···O1ii	0.93	2.41	3.295 (4)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯S1i	0.86	2.50	3.335 (3)	165
C4—H4A⋯O1ii	0.93	2.41	3.295 (4)	159

Symmetry codes: (i) ; (ii) .