3-Benzyl-8-meth­oxy-2-sulfanyl­idene-1,2,3,4-tetra­hydro­quinazolin-4-one

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

doi:10.1107/S1600536812021794

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1807

doi:10.1107/S1600536812021794

Open

access

3-Benzyl-8-methoxy-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 tetrahydroquinazole fused-ring system of the title compound, C₁₆H₁₄N₂O₂S, is roughly planar (r.m.s. deviation = 0.039 Å); the phenyl ring of the benzyl substituent is aligned at 78.1 (1)° with respect to the mean plane of the fused-ring system. In the crystal, two molecules are linked by a pair of N—H⋯S hydrogen bonds about a center of inversion, generating a dimer.

Related literature

For the synthesis, see: Al-Omar et al. (2004 ).

Experimental

Crystal data

C₁₆H₁₄N₂O₂S
M_r = 298.35
Triclinic, $[P \overline 1]$
a = 6.3025 (5) Å
b = 10.8353 (5) Å
c = 11.0144 (7) Å
α = 101.728 (5)°
β = 102.419 (6)°
γ = 101.693 (5)°
V = 694.95 (8) Å³
Z = 2
Cu Kα radiation
μ = 2.12 mm⁻¹
T = 294 K
0.40 × 0.30 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) T_min = 0.484, T_max = 0.676
11149 measured reflections
2888 independent reflections
2714 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.114
S = 1.06
2888 reflections
195 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S1ⁱ	0.87 (1)	2.63 (1)	3.493 (1)	174 (2)
Symmetry code: (i) -x+2, -y+2, -z+1.

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/S1600536812021794/bt5918sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812021794/bt5918Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812021794/bt5918Isup3.cml

checkCIF report

Comment top

The compound (Scheme I) was previously synthesized for a study of its antimicrobial activity. The background to this class of compounds is discussed (Al-Omar et al., 2004). The tetrahydroquinazole fused-ring of C₁₆H₁₄N₂O₂S is flat; the phenyl ring of the benzyl substituent is aligned at 78.1 (1) ° with respect to the fused-ring (Fig. 1). Two molecules are linked by an N–H···S hydrogen bond about a center of inversion to generate a dimer (Table 1).

Related literature top

For the synthesis, see: Al-Omar et al. (2004).

Experimental top

Benzyl isothiocyanate (10 mmol, 1.35 g), 2-amino-3-methoxybenzoic acid (10 mmol,1.67 g) and triethylamine (5 mmol, 0.51 g) in ethanol (30 ml) was heated under reflux for two hours. After cooling, the mixture was poured into ice-cold water. The resulting solid was filtered, washed with water and dried. Recrystallization from ethanol gave 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 C₁₆H₁₄N₂O₂S at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

3-Benzyl-8-methoxy-2-sulfanylidene-1,2,3,4-tetrahydroquinazolin-4-one top

Crystal data top

C₁₆H₁₄N₂O₂S	Z = 2
M_r = 298.35	F(000) = 312
Triclinic, P1	D_x = 1.426 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 6.3025 (5) Å	Cell parameters from 6739 reflections
b = 10.8353 (5) Å	θ = 4.3–76.5°
c = 11.0144 (7) Å	µ = 2.12 mm⁻¹
α = 101.728 (5)°	T = 294 K
β = 102.419 (6)°	Prism, colorless
γ = 101.693 (5)°	0.40 × 0.30 × 0.20 mm
V = 694.95 (8) Å³

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2888 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2714 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.026
Detector resolution: 10.4041 pixels mm^-1	θ_max = 76.7°, θ_min = 4.3°
ω scan	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −13→13
T_min = 0.484, T_max = 0.676	l = −13→13
11149 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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0717P)² + 0.1365P] where P = (F_o² + 2F_c²)/3
2888 reflections	(Δ/σ)_max = 0.001
195 parameters	Δρ_max = 0.22 e Å⁻³
1 restraint	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₁₆H₁₄N₂O₂S	γ = 101.693 (5)°
M_r = 298.35	V = 694.95 (8) Å³
Triclinic, P1	Z = 2
a = 6.3025 (5) Å	Cu Kα radiation
b = 10.8353 (5) Å	µ = 2.12 mm⁻¹
c = 11.0144 (7) Å	T = 294 K
α = 101.728 (5)°	0.40 × 0.30 × 0.20 mm
β = 102.419 (6)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2888 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	2714 reflections with I > 2σ(I)
T_min = 0.484, T_max = 0.676	R_int = 0.026
11149 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	1 restraint
wR(F²) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.22 e Å⁻³
2888 reflections	Δρ_min = −0.40 e Å⁻³
195 parameters

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

	x	y	z	U_iso*/U_eq
S1	0.84360 (6)	1.04442 (3)	0.64336 (3)	0.04455 (15)
O1	0.15151 (18)	0.69504 (12)	0.56998 (12)	0.0543 (3)
O2	0.8326 (2)	0.67738 (11)	0.27822 (11)	0.0509 (3)
N1	0.7112 (2)	0.81847 (12)	0.46983 (11)	0.0376 (3)
H1	0.829 (2)	0.8501 (18)	0.4456 (18)	0.051 (5)*
N2	0.47878 (18)	0.84651 (11)	0.60456 (11)	0.0355 (3)
C1	0.3257 (2)	0.72495 (14)	0.53999 (14)	0.0400 (3)
C2	0.3924 (2)	0.64174 (14)	0.44134 (13)	0.0388 (3)
C3	0.2672 (3)	0.51250 (15)	0.38286 (15)	0.0471 (3)
H3	0.1396	0.4778	0.4067	0.057*
C4	0.3356 (3)	0.43832 (15)	0.29020 (17)	0.0518 (4)
H4	0.2549	0.3520	0.2525	0.062*
C5	0.5233 (3)	0.48904 (16)	0.25080 (16)	0.0485 (4)
H5	0.5643	0.4374	0.1860	0.058*
C6	0.6480 (3)	0.61582 (14)	0.30800 (13)	0.0408 (3)
C7	0.5842 (2)	0.69243 (13)	0.40631 (13)	0.0363 (3)
C8	0.6691 (2)	0.89590 (13)	0.56926 (12)	0.0345 (3)
C9	0.8974 (3)	0.60835 (19)	0.17369 (17)	0.0571 (4)
H9A	1.0333	0.6606	0.1652	0.086*
H9B	0.7802	0.5900	0.0957	0.086*
H9C	0.9225	0.5279	0.1897	0.086*
C10	0.4113 (2)	0.92622 (14)	0.70865 (14)	0.0397 (3)
H10A	0.2568	0.9289	0.6768	0.048*
H10B	0.5053	1.0148	0.7331	0.048*
C11	0.4320 (2)	0.87257 (13)	0.82580 (13)	0.0401 (3)
C12	0.6395 (3)	0.88228 (16)	0.90532 (16)	0.0501 (4)
H12	0.7699	0.9204	0.8860	0.060*
C13	0.6537 (4)	0.8349 (2)	1.01459 (18)	0.0662 (5)
H13	0.7937	0.8417	1.0682	0.079*
C14	0.4613 (5)	0.77823 (19)	1.04350 (18)	0.0698 (6)
H14	0.4714	0.7466	1.1164	0.084*
C15	0.2558 (4)	0.76845 (19)	0.96517 (19)	0.0666 (5)
H15	0.1258	0.7299	0.9846	0.080*
C16	0.2402 (3)	0.81568 (17)	0.85676 (16)	0.0524 (4)
H16	0.0994	0.8091	0.8041	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0432 (2)	0.0386 (2)	0.0452 (2)	−0.00269 (15)	0.01814 (16)	0.00262 (15)
O1	0.0405 (6)	0.0597 (7)	0.0568 (7)	−0.0045 (5)	0.0229 (5)	0.0089 (5)
O2	0.0567 (7)	0.0465 (6)	0.0483 (6)	0.0031 (5)	0.0278 (5)	0.0052 (5)
N1	0.0370 (6)	0.0377 (6)	0.0364 (6)	0.0019 (5)	0.0151 (5)	0.0081 (5)
N2	0.0347 (6)	0.0383 (6)	0.0344 (6)	0.0057 (4)	0.0133 (4)	0.0109 (4)
C1	0.0357 (7)	0.0444 (8)	0.0375 (7)	0.0020 (6)	0.0101 (5)	0.0133 (6)
C2	0.0385 (7)	0.0392 (7)	0.0358 (7)	0.0029 (5)	0.0093 (5)	0.0112 (5)
C3	0.0429 (8)	0.0429 (8)	0.0493 (8)	−0.0027 (6)	0.0117 (6)	0.0124 (6)
C4	0.0542 (9)	0.0365 (7)	0.0540 (9)	−0.0016 (6)	0.0102 (7)	0.0059 (6)
C5	0.0572 (9)	0.0399 (7)	0.0443 (8)	0.0088 (6)	0.0140 (7)	0.0046 (6)
C6	0.0451 (7)	0.0410 (7)	0.0359 (7)	0.0069 (6)	0.0130 (6)	0.0109 (6)
C7	0.0381 (7)	0.0356 (6)	0.0329 (6)	0.0042 (5)	0.0086 (5)	0.0103 (5)
C8	0.0341 (6)	0.0378 (6)	0.0322 (6)	0.0060 (5)	0.0102 (5)	0.0125 (5)
C9	0.0654 (10)	0.0620 (10)	0.0522 (9)	0.0205 (8)	0.0308 (8)	0.0125 (8)
C10	0.0408 (7)	0.0401 (7)	0.0436 (7)	0.0107 (6)	0.0197 (6)	0.0131 (6)
C11	0.0488 (8)	0.0365 (7)	0.0373 (7)	0.0100 (6)	0.0194 (6)	0.0073 (5)
C12	0.0569 (9)	0.0475 (8)	0.0447 (8)	0.0141 (7)	0.0152 (7)	0.0070 (6)
C13	0.0895 (14)	0.0593 (10)	0.0468 (9)	0.0304 (10)	0.0055 (9)	0.0092 (8)
C14	0.1235 (19)	0.0547 (10)	0.0453 (9)	0.0316 (11)	0.0372 (11)	0.0198 (8)
C15	0.0951 (15)	0.0585 (10)	0.0608 (11)	0.0161 (10)	0.0477 (11)	0.0228 (9)
C16	0.0576 (9)	0.0531 (9)	0.0520 (9)	0.0094 (7)	0.0291 (7)	0.0149 (7)

Geometric parameters (Å, º) top

S1—C8	1.6818 (14)	C6—C7	1.407 (2)
O1—C1	1.2141 (18)	C9—H9A	0.9600
O2—C6	1.3582 (18)	C9—H9B	0.9600
O2—C9	1.4241 (19)	C9—H9C	0.9600
N1—C8	1.3475 (18)	C10—C11	1.5110 (19)
N1—C7	1.3867 (18)	C10—H10A	0.9700
N1—H1	0.868 (9)	C10—H10B	0.9700
N2—C8	1.3787 (17)	C11—C12	1.379 (2)
N2—C1	1.4074 (18)	C11—C16	1.385 (2)
N2—C10	1.4822 (17)	C12—C13	1.394 (3)
C1—C2	1.457 (2)	C12—H12	0.9300
C2—C7	1.3888 (19)	C13—C14	1.376 (3)
C2—C3	1.402 (2)	C13—H13	0.9300
C3—C4	1.367 (2)	C14—C15	1.364 (3)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.394 (2)	C15—C16	1.384 (2)
C4—H4	0.9300	C15—H15	0.9300
C5—C6	1.378 (2)	C16—H16	0.9300
C5—H5	0.9300

C6—O2—C9	117.68 (13)	O2—C9—H9A	109.5
C8—N1—C7	124.75 (12)	O2—C9—H9B	109.5
C8—N1—H1	116.9 (14)	H9A—C9—H9B	109.5
C7—N1—H1	118.4 (14)	O2—C9—H9C	109.5
C8—N2—C1	123.99 (12)	H9A—C9—H9C	109.5
C8—N2—C10	120.75 (11)	H9B—C9—H9C	109.5
C1—N2—C10	115.03 (11)	N2—C10—C11	112.13 (11)
O1—C1—N2	119.33 (14)	N2—C10—H10A	109.2
O1—C1—C2	124.39 (13)	C11—C10—H10A	109.2
N2—C1—C2	116.28 (12)	N2—C10—H10B	109.2
C7—C2—C3	120.22 (14)	C11—C10—H10B	109.2
C7—C2—C1	118.79 (12)	H10A—C10—H10B	107.9
C3—C2—C1	120.99 (13)	C12—C11—C16	118.91 (14)
C4—C3—C2	118.92 (14)	C12—C11—C10	121.20 (13)
C4—C3—H3	120.5	C16—C11—C10	119.87 (14)
C2—C3—H3	120.5	C11—C12—C13	120.01 (18)
C3—C4—C5	121.60 (14)	C11—C12—H12	120.0
C3—C4—H4	119.2	C13—C12—H12	120.0
C5—C4—H4	119.2	C14—C13—C12	120.3 (2)
C6—C5—C4	119.91 (15)	C14—C13—H13	119.9
C6—C5—H5	120.0	C12—C13—H13	119.9
C4—C5—H5	120.0	C15—C14—C13	119.94 (17)
O2—C6—C5	125.90 (14)	C15—C14—H14	120.0
O2—C6—C7	114.79 (12)	C13—C14—H14	120.0
C5—C6—C7	119.31 (14)	C14—C15—C16	120.18 (19)
N1—C7—C2	119.13 (13)	C14—C15—H15	119.9
N1—C7—C6	120.88 (12)	C16—C15—H15	119.9
C2—C7—C6	119.99 (13)	C15—C16—C11	120.70 (18)
N1—C8—N2	116.47 (12)	C15—C16—H16	119.6
N1—C8—S1	120.25 (10)	C11—C16—H16	119.6
N2—C8—S1	123.28 (10)

C8—N2—C1—O1	−172.81 (13)	O2—C6—C7—N1	−3.0 (2)
C10—N2—C1—O1	1.76 (19)	C5—C6—C7—N1	177.19 (13)
C8—N2—C1—C2	8.29 (19)	O2—C6—C7—C2	177.30 (12)
C10—N2—C1—C2	−177.14 (11)	C5—C6—C7—C2	−2.5 (2)
O1—C1—C2—C7	173.21 (14)	C7—N1—C8—N2	−3.3 (2)
N2—C1—C2—C7	−7.96 (19)	C7—N1—C8—S1	176.82 (10)
O1—C1—C2—C3	−7.2 (2)	C1—N2—C8—N1	−2.82 (19)
N2—C1—C2—C3	171.67 (12)	C10—N2—C8—N1	−177.09 (11)
C7—C2—C3—C4	−0.8 (2)	C1—N2—C8—S1	177.03 (10)
C1—C2—C3—C4	179.61 (14)	C10—N2—C8—S1	2.76 (18)
C2—C3—C4—C5	−1.4 (3)	C8—N2—C10—C11	−112.55 (14)
C3—C4—C5—C6	1.7 (3)	C1—N2—C10—C11	72.68 (15)
C9—O2—C6—C5	3.9 (2)	N2—C10—C11—C12	72.02 (17)
C9—O2—C6—C7	−175.88 (14)	N2—C10—C11—C16	−109.81 (15)
C4—C5—C6—O2	−179.43 (14)	C16—C11—C12—C13	0.2 (2)
C4—C5—C6—C7	0.3 (2)	C10—C11—C12—C13	178.36 (14)
C8—N1—C7—C2	3.3 (2)	C11—C12—C13—C14	0.1 (3)
C8—N1—C7—C6	−176.38 (12)	C12—C13—C14—C15	−0.1 (3)
C3—C2—C7—N1	−176.96 (12)	C13—C14—C15—C16	−0.1 (3)
C1—C2—C7—N1	2.7 (2)	C14—C15—C16—C11	0.4 (3)
C3—C2—C7—C6	2.7 (2)	C12—C11—C16—C15	−0.4 (2)
C1—C2—C7—C6	−177.66 (12)	C10—C11—C16—C15	−178.65 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1ⁱ	0.87 (1)	2.63 (1)	3.493 (1)	174 (2)

Symmetry code: (i) −x+2, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₄N₂O₂S
M_r	298.35
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	6.3025 (5), 10.8353 (5), 11.0144 (7)
α, β, γ (°)	101.728 (5), 102.419 (6), 101.693 (5)
V (Å³)	694.95 (8)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	2.12
Crystal size (mm)	0.40 × 0.30 × 0.20

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2012)
T_min, T_max	0.484, 0.676
No. of measured, independent and observed [I > 2σ(I)] reflections	11149, 2888, 2714
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.631

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.114, 1.06
No. of reflections	2888
No. of parameters	195
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)	0.22, −0.40

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···S1ⁱ	0.87 (1)	2.63 (1)	3.493 (1)	174 (2)

Symmetry code: (i) −x+2, −y+2, −z+1.

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

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Al-Omar, M. A., Abdel-Hamide, S. G., Al-Khamees, H. A. & El-Subbagh, H. I. (2004). Saudi Pharm. J. 12, 63–71. CAS Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar