3-(Prop-2-en-1-yl)-2-sulfanyl­idene-1,2,3,4-tetra­hydro­quinazolin-4-one

Abstract

The tetra­hydro­quinazoline fused-ring system of the title compound, C₁₁H₁₀N₂OS, is approximately planar (r.m.s. deviation = 0.019 Å). In the crystal, adjacent mol­ecules are linked by N—H⋯O hydrogen bonds, forming a chain running along the b axis.

Related literature  

For the synthesis, see: Shiau et al. (1990 ▶); Vassilev & Vassilev (2007 ▶).

Experimental  

Crystal data  

• C₁₁H₁₀N₂OS

• M _r = 218.27

• Monoclinic,

• a = 8.9823 (3) Å

• b = 13.7271 (3) Å

• c = 8.3137 (2) Å

• β = 92.882 (3)°

• V = 1023.79 (5) ų

• Z = 4

• Cu Kα radiation

• μ = 2.59 mm⁻¹

• T = 294 K

• 0.30 × 0.30 × 0.03 mm

Data collection  

• Agilent SuperNova Dual diffractometer with an Atlas detector

• Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T _min = 0.511, T _max = 0.927

• 4913 measured reflections

• 2128 independent reflections

• 1855 reflections with I > 2σ(I)

• R _int = 0.023

Refinement  

• R[F ² > 2σ(F ²)] = 0.037

• wR(F ²) = 0.108

• S = 1.06

• 2128 reflections

• 140 parameters

• 1 restraint

• H atoms treated by a mixture of independent and constrained refinement

• Δρ_max = 0.23 e Å⁻³

• Δρ_min = −0.38 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2012 ▶); 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: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Supplementary material file. DOI: 10.1107/S1600536812021800/bt5919Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.87 (1)	2.15 (1)	2.977 (2)	160 (2)

Symmetry code: (i) .

supplementary crystallographic information

Comment

The compound, 3-benzyl-8-methoxy-2-sulfanylidene-1,2,3,4-tetrahydroquinazolin-4-one, was previously synthesized for a study of its antimicrobial activity. The related 2-sulfanylidene-1,2,3,4-tetrahydroquinazolin-4-one (Scheme I) exhibits cytokinin activity (Vassilev & Vassilev, 2007). The synthesis described in the present study is a more straightforward procedure than those previously reported (Shiau et al., 1990; Vassilev & Vassilev, 2007). The tetrahydroquinazoline fused-ring of C₁₁H₁₀N₂OS is planar (Fig. 1). Adjacent molecules are linked by an N–H···O hydrogen to form a chain running along the b-axis of the monoclinic unit cell (Table 1).

Experimental

Allyl isothiocyanate (10 mmol, 0.99 g), 2-amino-5-methylbenzoic acid (10 mmol, 1.51 g) and triethylamine (5 mmol, 0.51 g) in ethanol (30 ml) was heated for two hours. The mixture was poured into ice-cold water. The solid was collected and recrystallized from ethanol to give colorless crystals.

Refinement

All H-atom were located in a difference Fourier map. Carbon-bound H-atoms were placed in calculated positions [C–H 0.93 to 0.97 Å, U_iso(H) 1.2U_eq(C)] and were included in the refinement in the riding model approximation.

The amino H-atom was refined isotropically with a distance restraint of N–H 0.88±0.01 Å.

Figures

Fig. 1.

Anisotropic displacement ellipsoid plot (Barbour, 2001) of C11H10N2OS at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Fig. 2.

Hydrogen-bond chain structure.

Crystal data

C11H10N2OS	F(000) = 456
Mr = 218.27	Dx = 1.416 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 2303 reflections
a = 8.9823 (3) Å	θ = 3.2–76.4°
b = 13.7271 (3) Å	µ = 2.59 mm−1
c = 8.3137 (2) Å	T = 294 K
β = 92.882 (3)°	Prism, colorless
V = 1023.79 (5) Å3	0.30 × 0.30 × 0.03 mm
Z = 4

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector	2128 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	1855 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.023
Detector resolution: 10.4041 pixels mm-1	θmax = 76.6°, θmin = 5.9°
ω scan	h = −11→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −17→10
Tmin = 0.511, Tmax = 0.927	l = −10→8
4913 measured reflections

Refinement

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0596P)2 + 0.1451P] where P = (Fo2 + 2Fc2)/3
2128 reflections	(Δ/σ)max = 0.001
140 parameters	Δρmax = 0.23 e Å−3
1 restraint	Δρmin = −0.38 e Å−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.77201 (5)	0.32274 (3)	0.07911 (5)	0.04374 (16)
O1	0.54446 (14)	0.00715 (8)	0.22169 (16)	0.0488 (3)
N1	0.53208 (14)	0.29760 (9)	0.24120 (16)	0.0337 (3)
H1	0.530 (2)	0.3608 (7)	0.239 (2)	0.052 (6)*
N2	0.64135 (14)	0.15416 (9)	0.15732 (15)	0.0317 (3)
C1	0.64308 (17)	0.25505 (10)	0.16333 (17)	0.0317 (3)
C2	0.53764 (17)	0.09571 (11)	0.23320 (18)	0.0341 (3)
C3	0.42514 (16)	0.14680 (11)	0.32027 (18)	0.0320 (3)
C4	0.31809 (19)	0.09589 (12)	0.4035 (2)	0.0404 (4)
H4	0.3200	0.0282	0.4068	0.048*
C5	0.2099 (2)	0.14630 (14)	0.4804 (2)	0.0458 (4)
H5	0.1379	0.1125	0.5345	0.055*
C6	0.20775 (19)	0.24781 (14)	0.4776 (2)	0.0445 (4)
H6	0.1339	0.2813	0.5293	0.053*
C7	0.3140 (2)	0.29896 (11)	0.3990 (2)	0.0393 (4)
H7	0.3127	0.3667	0.3982	0.047*
C8	0.42342 (16)	0.24836 (11)	0.32063 (17)	0.0311 (3)
C9	0.76129 (18)	0.10324 (12)	0.07515 (18)	0.0376 (4)
H9A	0.7907	0.1420	−0.0155	0.045*
H9B	0.7242	0.0412	0.0340	0.045*
C10	0.89456 (19)	0.08610 (13)	0.1881 (2)	0.0433 (4)
H10	0.9300	0.1382	0.2505	0.052*
C11	0.9639 (2)	0.00289 (15)	0.2043 (3)	0.0568 (5)
H11A	0.9313	−0.0506	0.1436	0.068*
H11B	1.0459	−0.0029	0.2765	0.068*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
S1	0.0415 (3)	0.0325 (2)	0.0586 (3)	−0.00599 (15)	0.01623 (19)	0.00349 (16)
O1	0.0559 (7)	0.0207 (5)	0.0712 (8)	−0.0015 (5)	0.0180 (6)	−0.0008 (5)
N1	0.0363 (7)	0.0203 (6)	0.0448 (7)	0.0004 (5)	0.0068 (6)	0.0020 (5)
N2	0.0324 (6)	0.0236 (6)	0.0393 (6)	0.0015 (5)	0.0055 (5)	−0.0004 (5)
C1	0.0328 (7)	0.0252 (6)	0.0369 (7)	−0.0002 (5)	0.0014 (6)	0.0009 (5)
C2	0.0358 (8)	0.0252 (7)	0.0414 (8)	−0.0004 (6)	0.0014 (6)	0.0025 (6)
C3	0.0319 (7)	0.0254 (7)	0.0387 (7)	−0.0019 (6)	0.0015 (6)	0.0016 (5)
C4	0.0406 (9)	0.0305 (7)	0.0505 (9)	−0.0053 (6)	0.0072 (7)	0.0044 (6)
C5	0.0414 (9)	0.0461 (9)	0.0511 (9)	−0.0086 (7)	0.0141 (7)	0.0039 (7)
C6	0.0383 (9)	0.0460 (9)	0.0502 (9)	0.0042 (7)	0.0124 (7)	−0.0006 (7)
C7	0.0407 (9)	0.0301 (7)	0.0477 (9)	0.0047 (6)	0.0086 (7)	0.0007 (6)
C8	0.0308 (7)	0.0265 (7)	0.0358 (7)	0.0001 (5)	0.0009 (6)	0.0020 (5)
C9	0.0408 (9)	0.0316 (8)	0.0413 (8)	0.0052 (6)	0.0103 (7)	−0.0015 (6)
C10	0.0382 (8)	0.0422 (9)	0.0502 (9)	0.0042 (7)	0.0092 (7)	−0.0025 (7)
C11	0.0431 (10)	0.0497 (10)	0.0774 (13)	0.0049 (8)	0.0004 (9)	0.0047 (9)

Geometric parameters (Å, º)

S1—C1	1.6663 (15)	C5—C6	1.394 (3)
O1—C2	1.2212 (18)	C5—H5	0.9300
N1—C1	1.3487 (19)	C6—C7	1.376 (2)
N1—C8	1.3822 (19)	C6—H6	0.9300
N1—H1	0.869 (9)	C7—C8	1.392 (2)
N2—C1	1.3858 (17)	C7—H7	0.9300
N2—C2	1.4031 (19)	C9—C10	1.502 (2)
N2—C9	1.4799 (18)	C9—H9A	0.9700
C2—C3	1.453 (2)	C9—H9B	0.9700
C3—C8	1.394 (2)	C10—C11	1.305 (3)
C3—C4	1.399 (2)	C10—H10	0.9300
C4—C5	1.377 (2)	C11—H11A	0.9300
C4—H4	0.9300	C11—H11B	0.9300
C1—N1—C8	125.05 (13)	C7—C6—C5	120.60 (15)
C1—N1—H1	116.1 (14)	C7—C6—H6	119.7
C8—N1—H1	118.8 (14)	C5—C6—H6	119.7
C1—N2—C2	124.18 (12)	C6—C7—C8	119.37 (15)
C1—N2—C9	118.79 (12)	C6—C7—H7	120.3
C2—N2—C9	116.91 (12)	C8—C7—H7	120.3
N1—C1—N2	116.28 (13)	N1—C8—C7	120.78 (14)
N1—C1—S1	120.42 (11)	N1—C8—C3	118.67 (13)
N2—C1—S1	123.29 (11)	C7—C8—C3	120.55 (14)
O1—C2—N2	119.80 (14)	N2—C9—C10	111.18 (12)
O1—C2—C3	123.95 (14)	N2—C9—H9A	109.4
N2—C2—C3	116.24 (13)	C10—C9—H9A	109.4
C8—C3—C4	119.36 (14)	N2—C9—H9B	109.4
C8—C3—C2	119.46 (13)	C10—C9—H9B	109.4
C4—C3—C2	121.18 (14)	H9A—C9—H9B	108.0
C5—C4—C3	119.84 (15)	C11—C10—C9	124.25 (18)
C5—C4—H4	120.1	C11—C10—H10	117.9
C3—C4—H4	120.1	C9—C10—H10	117.9
C4—C5—C6	120.25 (15)	C10—C11—H11A	120.0
C4—C5—H5	119.9	C10—C11—H11B	120.0
C6—C5—H5	119.9	H11A—C11—H11B	120.0
C8—N1—C1—N2	3.4 (2)	C2—C3—C4—C5	−177.85 (15)
C8—N1—C1—S1	−177.21 (12)	C3—C4—C5—C6	−0.9 (3)
C2—N2—C1—N1	−3.4 (2)	C4—C5—C6—C7	−0.4 (3)
C9—N2—C1—N1	−179.29 (13)	C5—C6—C7—C8	0.6 (3)
C2—N2—C1—S1	177.16 (11)	C1—N1—C8—C7	179.38 (14)
C9—N2—C1—S1	1.30 (19)	C1—N1—C8—C3	−0.9 (2)
C1—N2—C2—O1	−179.93 (14)	C6—C7—C8—N1	−179.70 (15)
C9—N2—C2—O1	−4.0 (2)	C6—C7—C8—C3	0.5 (2)
C1—N2—C2—C3	1.0 (2)	C4—C3—C8—N1	178.43 (14)
C9—N2—C2—C3	176.97 (12)	C2—C3—C8—N1	−1.7 (2)
O1—C2—C3—C8	−177.37 (15)	C4—C3—C8—C7	−1.8 (2)
N2—C2—C3—C8	1.6 (2)	C2—C3—C8—C7	178.01 (14)
O1—C2—C3—C4	2.4 (2)	C1—N2—C9—C10	86.69 (17)
N2—C2—C3—C4	−178.57 (14)	C2—N2—C9—C10	−89.46 (16)
C8—C3—C4—C5	2.0 (2)	N2—C9—C10—C11	132.15 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.87 (1)	2.15 (1)	2.977 (2)	160 (2)

Symmetry code: (i) −x+1, y+1/2, −z+1/2.