6-Methyl-3-phenyl-2-sulfanyl-idene-1,2,3,4-tetra-hydro-quinazolin-4-one.

The title compound, C(15)H(12)N(2)OS, exists as the thione tautomer in the solid state. The phenyl group is almost perpendicular [dihedral angle = 87.96 (5)°] to the fused ring system (r.m.s. deviation = 0.036 Å for 13 ring and exocyclic non-H atoms). In the crystal, centrosymmetric dimers, sustained by pairs of N-H⋯S hydrogen bonds, are connected into layers parallel to (-101) by C-H⋯O and C-H⋯S inter-actions.

Related literature

For recent studies on synthesis, drug discovery and crystal structures of quinazoline-4(3H)-one derivatives, see: El-Azab & El-Tahir (2012 ▶); El-Azab et al. (2011 ▶, 2010 ▶). For the anti­microbial activity of the title compound, see: Al-Omar et al. (2004 ▶). For the structures of related compounds, see: Bowman et al. (2007 ▶); Hashim et al. (2010 ▶).

Experimental

Crystal data

C15H12N2OS

M = 268.33

Monoclinic,

a = 12.7770 (3) Å

b = 5.1384 (1) Å

c = 19.0973 (4) Å

β = 91.814 (2)°

V = 1253.17 (5) Å3

Z = 4

Cu Kα radiation

μ = 2.23 mm−1

T = 100 K

0.35 × 0.15 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.967, T max = 0.998

4636 measured reflections

2576 independent reflections

2348 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.098

S = 1.06

2576 reflections

177 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812007301/qm2054sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812007301/qm2054Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812007301/qm2054Isup3.cml

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

C15H12N2OS	F(000) = 560
Mr = 268.33	Dx = 1.422 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 2386 reflections
a = 12.7770 (3) Å	θ = 3.5–76.4°
b = 5.1384 (1) Å	µ = 2.23 mm−1
c = 19.0973 (4) Å	T = 100 K
β = 91.814 (2)°	Prism, colourless
V = 1253.17 (5) Å3	0.35 × 0.15 × 0.05 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	2576 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2348 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.016
Detector resolution: 10.4041 pixels mm-1	θmax = 76.6°, θmin = 4.1°
ω scan	h = −15→16
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −5→6
Tmin = 0.967, Tmax = 0.998	l = −14→24
4636 measured reflections

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0613P)2 + 0.3083P] where P = (Fo2 + 2Fc2)/3
2576 reflections	(Δ/σ)max = 0.001
177 parameters	Δρmax = 0.25 e Å−3
0 restraints	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.

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 > σ(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	0.56616 (3)	0.52832 (7)	0.394981 (16)	0.01717 (12)
O1	0.35822 (8)	−0.1192 (2)	0.25706 (5)	0.0181 (2)
N1	0.45653 (9)	0.1596 (2)	0.32532 (6)	0.0149 (2)
H1n	0.4357 (15)	0.305 (4)	0.4827 (11)	0.029 (5)*
N2	0.42228 (9)	0.2138 (2)	0.44293 (6)	0.0161 (2)
C1	0.37571 (11)	−0.0266 (3)	0.31493 (7)	0.0150 (3)
C2	0.31942 (10)	−0.0982 (3)	0.37768 (7)	0.0156 (3)
C3	0.24261 (10)	−0.2920 (3)	0.37432 (7)	0.0173 (3)
H3	0.2250	−0.3722	0.3307	0.021*
C4	0.19179 (11)	−0.3686 (3)	0.43408 (7)	0.0182 (3)
C5	0.22073 (11)	−0.2484 (3)	0.49797 (7)	0.0195 (3)
H5	0.1871	−0.3001	0.5394	0.023*
C6	0.29690 (11)	−0.0568 (3)	0.50213 (7)	0.0179 (3)
H6	0.3156	0.0210	0.5459	0.021*
C7	0.34592 (11)	0.0206 (3)	0.44129 (7)	0.0156 (3)
C9	0.47714 (10)	0.2888 (3)	0.38744 (7)	0.0149 (3)
C8	0.10873 (12)	−0.5770 (3)	0.42997 (8)	0.0229 (3)
H8A	0.1314	−0.7176	0.3993	0.034*
H8B	0.0432	−0.5024	0.4110	0.034*
H8C	0.0976	−0.6465	0.4769	0.034*
C10	0.52338 (10)	0.2014 (3)	0.26589 (7)	0.0154 (3)
C11	0.60838 (11)	0.0364 (3)	0.25902 (8)	0.0188 (3)
H11	0.6233	−0.0942	0.2931	0.023*
C12	0.67148 (12)	0.0652 (3)	0.20130 (8)	0.0208 (3)
H12	0.7303	−0.0452	0.1959	0.025*
C13	0.64818 (11)	0.2554 (3)	0.15178 (7)	0.0208 (3)
H13	0.6910	0.2746	0.1124	0.025*
C14	0.56249 (12)	0.4182 (3)	0.15946 (7)	0.0217 (3)
H14	0.5471	0.5485	0.1254	0.026*
C15	0.49894 (11)	0.3912 (3)	0.21705 (7)	0.0193 (3)
H15	0.4400	0.5013	0.2225	0.023*

	U11	U22	U33	U12	U13	U23
S1	0.0194 (2)	0.01951 (19)	0.01264 (19)	−0.00399 (12)	0.00160 (13)	−0.00051 (12)
O1	0.0211 (5)	0.0210 (5)	0.0122 (5)	−0.0004 (4)	−0.0006 (4)	−0.0024 (4)
N1	0.0169 (5)	0.0178 (6)	0.0102 (5)	−0.0002 (4)	0.0019 (4)	−0.0005 (4)
N2	0.0189 (6)	0.0194 (6)	0.0101 (5)	−0.0025 (5)	0.0016 (4)	−0.0016 (5)
C1	0.0154 (6)	0.0161 (6)	0.0136 (6)	0.0029 (5)	−0.0003 (5)	0.0006 (5)
C2	0.0156 (6)	0.0179 (6)	0.0132 (6)	0.0015 (5)	0.0007 (5)	0.0012 (5)
C3	0.0168 (6)	0.0197 (7)	0.0153 (6)	0.0001 (5)	−0.0004 (5)	−0.0009 (5)
C4	0.0158 (6)	0.0190 (7)	0.0199 (7)	0.0012 (5)	0.0008 (5)	0.0013 (5)
C5	0.0193 (6)	0.0229 (7)	0.0165 (6)	0.0013 (5)	0.0052 (5)	0.0029 (6)
C6	0.0201 (7)	0.0212 (7)	0.0125 (6)	0.0008 (5)	0.0023 (5)	−0.0002 (5)
C7	0.0145 (6)	0.0176 (6)	0.0145 (6)	0.0011 (5)	0.0005 (5)	0.0002 (5)
C9	0.0155 (6)	0.0163 (6)	0.0129 (6)	0.0015 (5)	0.0002 (5)	0.0004 (5)
C8	0.0198 (7)	0.0245 (7)	0.0245 (7)	−0.0038 (6)	0.0032 (6)	0.0017 (6)
C10	0.0176 (6)	0.0183 (6)	0.0103 (6)	−0.0027 (5)	0.0026 (5)	−0.0021 (5)
C11	0.0199 (7)	0.0199 (7)	0.0166 (7)	0.0013 (5)	0.0024 (5)	0.0032 (5)
C12	0.0187 (7)	0.0225 (7)	0.0213 (7)	0.0011 (6)	0.0056 (6)	−0.0005 (6)
C13	0.0230 (7)	0.0249 (7)	0.0148 (6)	−0.0055 (6)	0.0060 (5)	−0.0011 (6)
C14	0.0283 (8)	0.0220 (7)	0.0148 (7)	−0.0007 (6)	0.0024 (6)	0.0051 (6)
C15	0.0226 (7)	0.0192 (7)	0.0161 (6)	0.0025 (6)	0.0024 (5)	−0.0008 (6)

S1—C9	1.6788 (14)	C6—C7	1.3953 (19)
O1—C1	1.2175 (17)	C6—H6	0.9500
N1—C9	1.3776 (17)	C8—H8A	0.9800
N1—C1	1.4171 (18)	C8—H8B	0.9800
N1—C10	1.4578 (16)	C8—H8C	0.9800
N2—C9	1.3454 (17)	C10—C15	1.379 (2)
N2—C7	1.3913 (18)	C10—C11	1.388 (2)
N2—H1n	0.91 (2)	C11—C12	1.3940 (19)
C1—C2	1.4639 (18)	C11—H11	0.9500
C2—C7	1.3918 (19)	C12—C13	1.386 (2)
C2—C3	1.398 (2)	C12—H12	0.9500
C3—C4	1.3877 (19)	C13—C14	1.389 (2)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.406 (2)	C14—C15	1.3945 (19)
C4—C8	1.508 (2)	C14—H14	0.9500
C5—C6	1.385 (2)	C15—H15	0.9500
C5—H5	0.9500
C9—N1—C1	124.38 (11)	N2—C9—N1	116.73 (12)
C9—N1—C10	119.89 (11)	N2—C9—S1	120.73 (10)
C1—N1—C10	115.66 (11)	N1—C9—S1	122.54 (10)
C9—N2—C7	124.69 (12)	C4—C8—H8A	109.5
C9—N2—H1n	115.0 (13)	C4—C8—H8B	109.5
C7—N2—H1n	120.2 (13)	H8A—C8—H8B	109.5
O1—C1—N1	120.20 (12)	C4—C8—H8C	109.5
O1—C1—C2	124.34 (13)	H8A—C8—H8C	109.5
N1—C1—C2	115.45 (12)	H8B—C8—H8C	109.5
C7—C2—C3	120.25 (12)	C15—C10—C11	121.98 (12)
C7—C2—C1	119.46 (13)	C15—C10—N1	120.36 (12)
C3—C2—C1	120.24 (12)	C11—C10—N1	117.59 (12)
C4—C3—C2	120.66 (13)	C10—C11—C12	118.93 (13)
C4—C3—H3	119.7	C10—C11—H11	120.5
C2—C3—H3	119.7	C12—C11—H11	120.5
C3—C4—C5	118.17 (13)	C13—C12—C11	119.84 (14)
C3—C4—C8	120.35 (13)	C13—C12—H12	120.1
C5—C4—C8	121.48 (13)	C11—C12—H12	120.1
C6—C5—C4	121.79 (13)	C12—C13—C14	120.37 (13)
C6—C5—H5	119.1	C12—C13—H13	119.8
C4—C5—H5	119.1	C14—C13—H13	119.8
C5—C6—C7	119.22 (13)	C13—C14—C15	120.25 (13)
C5—C6—H6	120.4	C13—C14—H14	119.9
C7—C6—H6	120.4	C15—C14—H14	119.9
N2—C7—C2	118.93 (12)	C10—C15—C14	118.62 (13)
N2—C7—C6	121.17 (13)	C10—C15—H15	120.7
C2—C7—C6	119.90 (13)	C14—C15—H15	120.7
C9—N1—C1—O1	175.07 (13)	C5—C6—C7—N2	179.51 (13)
C10—N1—C1—O1	−7.96 (18)	C5—C6—C7—C2	−1.2 (2)
C9—N1—C1—C2	−6.19 (19)	C7—N2—C9—N1	−1.3 (2)
C10—N1—C1—C2	170.77 (11)	C7—N2—C9—S1	178.88 (10)
O1—C1—C2—C7	−179.92 (13)	C1—N1—C9—N2	6.2 (2)
N1—C1—C2—C7	1.40 (19)	C10—N1—C9—N2	−170.65 (12)
O1—C1—C2—C3	2.7 (2)	C1—N1—C9—S1	−173.97 (10)
N1—C1—C2—C3	−176.00 (12)	C10—N1—C9—S1	9.18 (18)
C7—C2—C3—C4	0.0 (2)	C9—N1—C10—C15	−91.74 (16)
C1—C2—C3—C4	177.40 (13)	C1—N1—C10—C15	91.15 (16)
C2—C3—C4—C5	−0.9 (2)	C9—N1—C10—C11	91.23 (16)
C2—C3—C4—C8	179.76 (13)	C1—N1—C10—C11	−85.88 (15)
C3—C4—C5—C6	0.6 (2)	C15—C10—C11—C12	0.6 (2)
C8—C4—C5—C6	−179.97 (13)	N1—C10—C11—C12	177.61 (13)
C4—C5—C6—C7	0.4 (2)	C10—C11—C12—C13	−0.5 (2)
C9—N2—C7—C2	−3.2 (2)	C11—C12—C13—C14	0.2 (2)
C9—N2—C7—C6	176.10 (13)	C12—C13—C14—C15	−0.2 (2)
C3—C2—C7—N2	−179.69 (12)	C11—C10—C15—C14	−0.6 (2)
C1—C2—C7—N2	2.9 (2)	N1—C10—C15—C14	−177.45 (13)
C3—C2—C7—C6	1.0 (2)	C13—C14—C15—C10	0.3 (2)
C1—C2—C7—C6	−176.36 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1n···S1i	0.91 (2)	2.49 (2)	3.3662 (12)	163.6 (17)
C3—H3···O1ii	0.95	2.33	3.2522 (17)	163
C11—H11···S1iii	0.95	2.86	3.7333 (16)	154
C15—H15···O1iv	0.95	2.32	3.1988 (18)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1n⋯S1i	0.91 (2)	2.49 (2)	3.3662 (12)	163.6 (17)
C3—H3⋯O1ii	0.95	2.33	3.2522 (17)	163
C11—H11⋯S1iii	0.95	2.86	3.7333 (16)	154
C15—H15⋯O1iv	0.95	2.32	3.1988 (18)	154

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .