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

Al-Salahi, R.; Al-Omar, M.; Marzouk, M.; Ng, S.W.

doi:10.1107/S1600536812021800

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1810

doi:10.1107/S1600536812021800

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

Rashad Al-Salahi,^a Mohamed Al-Omar,^a Mohamed Marzouk ^a and Seik Weng Ng ^b,^c ^*

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 10 May 2012; accepted 14 May 2012; online 19 May 2012)

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, P 2₁ /c
a = 8.9823 (3) Å
b = 13.7271 (3) Å
c = 8.3137 (2) Å
β = 92.882 (3)°
V = 1023.79 (5) Å³
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[F² > 2σ(F²)] = 0.037
wR(F²) = 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

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) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812021800/bt5919sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812021800/bt5919Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812021800/bt5919Isup3.cml

checkCIF report

Comment top

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).

Related literature top

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

Experimental top

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.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); 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).

Figures top

	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.

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

Crystal data top

C₁₁H₁₀N₂OS	F(000) = 456
M_r = 218.27	D_x = 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 top

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	R_int = 0.023
Detector resolution: 10.4041 pixels mm^-1	θ_max = 76.6°, θ_min = 5.9°
ω scan	h = −11→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −17→10
T_min = 0.511, T_max = 0.927	l = −10→8
4913 measured reflections

Refinement top

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(F_o²) + (0.0596P)² + 0.1451P] where P = (F_o² + 2F_c²)/3
2128 reflections	(Δ/σ)_max = 0.001
140 parameters	Δρ_max = 0.23 e Å⁻³
1 restraint	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₁₁H₁₀N₂OS	V = 1023.79 (5) Å³
M_r = 218.27	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 8.9823 (3) Å	µ = 2.59 mm⁻¹
b = 13.7271 (3) Å	T = 294 K
c = 8.3137 (2) Å	0.30 × 0.30 × 0.03 mm
β = 92.882 (3)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2128 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	1855 reflections with I > 2σ(I)
T_min = 0.511, T_max = 0.927	R_int = 0.023
4913 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	1 restraint
wR(F²) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.23 e Å⁻³
2128 reflections	Δρ_min = −0.38 e Å⁻³
140 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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) top

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) top

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.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₀N₂OS
M_r	218.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	8.9823 (3), 13.7271 (3), 8.3137 (2)
β (°)	92.882 (3)
V (Å³)	1023.79 (5)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	2.59
Crystal size (mm)	0.30 × 0.30 × 0.03

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2012)
T_min, T_max	0.511, 0.927
No. of measured, independent and observed [I > 2σ(I)] reflections	4913, 2128, 1855
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.631

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.108, 1.06
No. of reflections	2128
No. of parameters	140
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.38

Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

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.

Acknowledgements

We thank the Research Center of the College of Pharmacy College and Deanship of Scientific Research of King Saud University, and the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR/MOHE/SC/12) for supporting this study.

References

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