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

Abstract

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,

• 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) ų

• 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[F ² > 2σ(F ²)] = 0.038

• wR(F ²) = 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

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/S1600536812021794/bt5918Isup3.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⋯S1i	0.87 (1)	2.63 (1)	3.493 (1)	174 (2)

Symmetry code: (i) .

supplementary crystallographic information

Comment

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).

Experimental

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.

Refinement

All H-atoms 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) 1.2 to 1.5U_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 C16H14N2O2S at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C16H14N2O2S	Z = 2
Mr = 298.35	F(000) = 312
Triclinic, P1	Dx = 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

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	Rint = 0.026
Detector resolution: 10.4041 pixels mm-1	θmax = 76.7°, θmin = 4.3°
ω scan	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −13→13
Tmin = 0.484, Tmax = 0.676	l = −13→13
11149 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)] = 0.038	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(Fo2) + (0.0717P)2 + 0.1365P] where P = (Fo2 + 2Fc2)/3
2888 reflections	(Δ/σ)max = 0.001
195 parameters	Δρmax = 0.22 e Å−3
1 restraint	Δρmin = −0.40 e Å−3

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

	x	y	z	Uiso*/Ueq
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 (Ų)

	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)

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)

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.