7-(Benzyl­sulfan­yl)-5-(2-methoxy­phen­yl)-1,3-dimethyl-5,6-dihydro­pyrimido[4,5-d]pyrimidine-2,4(1H,3H)-dione

Bazgir, A.; Faraji, F.

doi:10.1107/S160053680802401X

organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1666

doi:10.1107/S160053680802401X

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7-(Benzylsulfanyl)-5-(2-methoxyphenyl)-1,3-dimethyl-5,6-dihydropyrimido[4,5-d]pyrimidine-2,4(1H,3H)-dione

Ayoob Bazgir ^a ^* and Fereshteh Faraji ^b

^aDepartment of Chemistry, Islamic Azad University, Dorood Branch, Dorood 688173551, Iran, and ^bDepartment of Chemistry, Faculty of Science, Islamic Azad University, Karaj Branch, Karaj, Iran
^*Correspondence e-mail: a_bazgir@yahoo.com

(Received 19 July 2008; accepted 29 July 2008; online 6 August 2008)

In the molecule of the title compound, C₂₂H₂₂N₄O₃S, the benzene and phenyl rings are oriented at a dihedral angle of 88.72 (4)°. The other two rings have flattened-boat conformations. In the crystal structure, intermolecular N—H⋯O hydrogen bonds link the molecules.

Related literature

For general background, see: Sharma et al. (2004 ); Quiroga et al. (2002 ); Devi et al. (2003 ). For bond-length data, see: Allen et al. (1987 ). For ring conformation puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₂H₂₂N₄O₃S
M_r = 422.51
Monoclinic, P 2₁ /n
a = 10.9216 (9) Å
b = 8.8528 (5) Å
c = 20.7263 (15) Å
β = 90.638 (6)°
V = 2003.8 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 294 (2) K
0.4 × 0.3 × 0.05 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ) T_min = 0.928, T_max = 0.985
23191 measured reflections
5394 independent reflections
4510 reflections with I > 2σ(I)
R_int = 0.063

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.135
S = 1.15
5394 reflections
278 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4B⋯O1ⁱ	0.85 (3)	2.02 (3)	2.836 (2)	161 (2)
Symmetry code: (i) x, y+1, z.

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680802401X/hk2501sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680802401X/hk2501Isup2.hkl

checkCIF report

Comment top

The importance of fused pyrimidines, common source for the development of new potential therapeutic agents (Sharma et al., 2004), is well known. Among them, the pyrimido[2,3-d]pyrimidines are an important class of annulated uracils with biological significance because of their connection with purine pteridine system (Quiroga et al., 2002). Numerous reports delineate the antitumor, antivial, antioxidant, antifungal and hepatoprotective activities of these compounds (Devi et al., 2003). Therefore, for the preparation of these complex molecules large efforts have been directed towards the synthetic manipulation of uracils. We report herein the synthesis and crystal structure of the title compound.

In the molecule of the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C1-C6) and D (C16-C21) are, of course, planar and they are oriented at a dihedral angle of A/D = 88.72 (4)°. Rings B (N2/N3/C9/C11/C13/C14) and C (N1/N4/C8/C9/C14/C15) have flattened-boat [ϕ = 105.63 (2)°, θ = 100.53 (3)° (for ring B) and ϕ = 29.58 (3)°, θ = 58.23 (3)° (for ring C)] conformations, having total puckering amplitudes, Q_T, of 0.120 (3) and 0.364 (3) Å, respectively (Cremer & Pople, 1975).

In the crystal structure, intermolecular N-H···O hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they may be effective in the stabilization of the structure.

Related literature top

For general background, see: Sharma et al. (2004); Quiroga et al. (2002); Devi et al. (2003). For bond-length data, see: Allen et al. (1987). For ring conformation puckering parameters, see: Cremer & Pople (1975).

Experimental top

For the preparation of the title compound, 6-amino-1,3-dimethyluracil (0.15 g, 1 mmol), 2-methylbenzaldehyde (0.12 g, 1 mmol), 2-benzylthiourea hydrochloride (0.30 g, 1.5 mmol) and p-toluenesulfonic acid (0.1 g) were mixed. The reaction mixture was placed in a screw capped vial and irradiated for 5 min with a power of 700 W microwave irradiation. After cooling, the reaction mixture was washed with water, and then recrystallized from ethyl acetate to afford the title compound (yield; 0.25 g. 65%, m.p. 519-521 K).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

7-(Benzylsulfanyl)-5-(2-methoxyphenyl)-1,3-dimethyl-5,6-dihydropyrimido[4,5-d]pyrimidine-2,4(1H,3H)-dione top

Crystal data top

C₂₂H₂₂N₄O₃S	F(000) = 888
M_r = 422.51	D_x = 1.401 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2175 reflections
a = 10.9216 (9) Å	θ = 2.1–29.3°
b = 8.8528 (5) Å	µ = 0.20 mm⁻¹
c = 20.7263 (15) Å	T = 294 K
β = 90.638 (6)°	Plate, colorless
V = 2003.8 (2) Å³	0.4 × 0.3 × 0.05 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	4510 reflections with I > 2σ(I)
ϕ and ω scans	R_int = 0.063
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	θ_max = 29.3°, θ_min = 2.1°
T_min = 0.928, T_max = 0.985	h = −14→15
23191 measured reflections	k = −11→12
5394 independent reflections	l = −28→28

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.055	w = 1/[σ²(F_o²) + (0.0538P)² + 0.6815P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.135	(Δ/σ)_max = 0.038
S = 1.15	Δρ_max = 0.32 e Å⁻³
5394 reflections	Δρ_min = −0.25 e Å⁻³
278 parameters

Crystal data top

C₂₂H₂₂N₄O₃S	V = 2003.8 (2) Å³
M_r = 422.51	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.9216 (9) Å	µ = 0.20 mm⁻¹
b = 8.8528 (5) Å	T = 294 K
c = 20.7263 (15) Å	0.4 × 0.3 × 0.05 mm
β = 90.638 (6)°

Data collection top

Bruker SMART CCD area-detector diffractometer	5394 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	4510 reflections with I > 2σ(I)
T_min = 0.928, T_max = 0.985	R_int = 0.063
23191 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.15	Δρ_max = 0.32 e Å⁻³
5394 reflections	Δρ_min = −0.25 e Å⁻³
278 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
S1	0.34470 (5)	0.84201 (5)	0.12120 (2)	0.04173 (13)
O1	0.34328 (15)	0.11232 (15)	−0.03830 (7)	0.0508 (4)
O2	0.32309 (14)	0.52289 (16)	−0.17071 (6)	0.0469 (3)
O3	0.08733 (11)	0.71339 (19)	0.00741 (7)	0.0502 (4)
N1	0.33713 (13)	0.57943 (16)	0.05837 (7)	0.0322 (3)
N2	0.34856 (13)	0.34559 (15)	0.00770 (7)	0.0320 (3)
N3	0.32991 (14)	0.31591 (16)	−0.10452 (7)	0.0349 (3)
N4	0.33864 (13)	0.80243 (16)	−0.00370 (7)	0.0326 (3)
H4B	0.341 (2)	0.898 (3)	−0.0043 (11)	0.049 (6)*
C1	0.15207 (19)	0.5279 (2)	0.18010 (10)	0.0459 (4)
H1	0.1982	0.4632	0.1547	0.055*
C2	0.0325 (2)	0.4896 (3)	0.19479 (10)	0.0509 (5)
H2	−0.0011	0.4002	0.179	0.061*
C3	−0.0368 (2)	0.5839 (3)	0.23278 (10)	0.0526 (5)
H3	−0.1169	0.5582	0.2429	0.063*
C4	0.0136 (2)	0.7165 (3)	0.25561 (11)	0.0592 (6)
H4	−0.0328	0.7807	0.2811	0.071*
C5	0.1329 (2)	0.7546 (3)	0.24080 (10)	0.0525 (5)
H5	0.1659	0.8443	0.2566	0.063*
C6	0.20406 (17)	0.6607 (2)	0.20257 (8)	0.0388 (4)
C7	0.33376 (18)	0.7042 (2)	0.18617 (9)	0.0432 (4)
H7A	0.3782	0.6139	0.1739	0.052*
H7B	0.3733	0.7453	0.2245	0.052*
C8	0.33809 (14)	0.72697 (18)	0.05202 (8)	0.0300 (3)
C9	0.33441 (13)	0.50102 (17)	0.00128 (8)	0.0288 (3)
C10	0.37101 (17)	0.2765 (2)	0.07119 (9)	0.0382 (4)
H10A	0.2942	0.2532	0.0909	0.057*
H10B	0.4159	0.3458	0.0981	0.057*
H10C	0.4176	0.1854	0.066	0.057*
C11	0.34047 (15)	0.25006 (18)	−0.04476 (9)	0.0345 (3)
C12	0.3234 (2)	0.2154 (2)	−0.16086 (10)	0.0483 (5)
H12A	0.3785	0.1321	−0.1546	0.072*
H12B	0.3461	0.2704	−0.1988	0.072*
H12C	0.2414	0.178	−0.166	0.072*
C13	0.32425 (15)	0.47335 (19)	−0.11530 (8)	0.0331 (3)
C14	0.31967 (14)	0.56353 (17)	−0.05833 (8)	0.0293 (3)
C15	0.30427 (14)	0.73269 (17)	−0.06556 (8)	0.0287 (3)
H15	0.3644	0.7662	−0.0973	0.034*
C16	0.17931 (14)	0.78714 (18)	−0.08936 (8)	0.0301 (3)
C17	0.16945 (17)	0.8519 (2)	−0.15010 (9)	0.0378 (4)
H17	0.2381	0.8546	−0.1762	0.045*
C18	0.0604 (2)	0.9128 (2)	−0.17325 (10)	0.0469 (5)
H18	0.0559	0.9551	−0.2143	0.056*
C19	−0.0411 (2)	0.9096 (3)	−0.13438 (11)	0.0532 (5)
H19	−0.1143	0.9515	−0.1491	0.064*
C20	−0.03502 (18)	0.8450 (3)	−0.07381 (10)	0.0493 (5)
H20	−0.1041	0.8439	−0.048	0.059*
C21	0.07381 (16)	0.7812 (2)	−0.05109 (9)	0.0371 (4)
C22	−0.0178 (2)	0.7044 (4)	0.04781 (13)	0.0771 (9)
H22A	−0.0516	0.8035	0.0535	0.116*
H22B	0.0057	0.6636	0.089	0.116*
H22C	−0.0781	0.64	0.028	0.116*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0512 (11)	0.0413 (10)	0.0454 (10)	0.0063 (8)	0.0071 (8)	−0.0019 (8)
C2	0.0550 (12)	0.0452 (11)	0.0528 (11)	−0.0047 (9)	0.0061 (9)	0.0045 (9)
C3	0.0478 (11)	0.0587 (13)	0.0515 (11)	0.0019 (10)	0.0107 (9)	0.0136 (10)
C4	0.0607 (14)	0.0600 (14)	0.0573 (13)	0.0121 (11)	0.0216 (11)	−0.0024 (11)
C5	0.0591 (13)	0.0489 (12)	0.0495 (11)	−0.0002 (9)	0.0081 (9)	−0.0100 (9)
C6	0.0425 (9)	0.0429 (10)	0.0311 (8)	0.0043 (7)	−0.0013 (7)	0.0027 (7)
C7	0.0402 (9)	0.0522 (11)	0.0372 (9)	0.0014 (8)	−0.0051 (7)	−0.0013 (8)
C8	0.0233 (7)	0.0286 (7)	0.0383 (8)	0.0005 (5)	0.0010 (6)	−0.0006 (6)
C9	0.0228 (7)	0.0239 (7)	0.0398 (8)	0.0006 (5)	0.0039 (6)	0.0030 (6)
C10	0.0377 (9)	0.0320 (8)	0.0447 (9)	0.0034 (7)	0.0009 (7)	0.0115 (7)
C11	0.0318 (8)	0.0251 (7)	0.0467 (9)	−0.0018 (6)	0.0029 (7)	0.0016 (7)
C12	0.0609 (12)	0.0340 (9)	0.0501 (11)	−0.0013 (9)	−0.0015 (9)	−0.0085 (8)
C13	0.0302 (8)	0.0285 (7)	0.0407 (8)	−0.0014 (6)	0.0046 (6)	0.0017 (7)
C14	0.0258 (7)	0.0242 (7)	0.0381 (8)	−0.0002 (5)	0.0027 (6)	0.0029 (6)
C15	0.0262 (7)	0.0242 (7)	0.0356 (8)	−0.0012 (5)	0.0034 (6)	0.0052 (6)
C16	0.0287 (7)	0.0246 (7)	0.0369 (8)	−0.0004 (6)	0.0005 (6)	0.0034 (6)
C17	0.0413 (9)	0.0327 (8)	0.0395 (9)	−0.0009 (7)	0.0007 (7)	0.0054 (7)
C18	0.0540 (12)	0.0421 (10)	0.0444 (10)	0.0064 (9)	−0.0092 (8)	0.0101 (8)
C19	0.0440 (11)	0.0559 (12)	0.0593 (12)	0.0163 (9)	−0.0118 (9)	0.0057 (10)
C20	0.0320 (9)	0.0632 (13)	0.0525 (11)	0.0102 (9)	0.0007 (8)	0.0039 (10)
C21	0.0303 (8)	0.0393 (9)	0.0415 (9)	0.0023 (7)	0.0007 (6)	0.0042 (7)
C22	0.0416 (12)	0.127 (3)	0.0628 (15)	0.0041 (14)	0.0173 (10)	0.0345 (16)
N1	0.0338 (7)	0.0268 (6)	0.0361 (7)	0.0024 (5)	0.0011 (5)	0.0018 (5)
N2	0.0324 (7)	0.0240 (6)	0.0396 (7)	0.0015 (5)	0.0024 (5)	0.0056 (5)
N3	0.0379 (7)	0.0257 (7)	0.0411 (7)	−0.0017 (5)	0.0034 (6)	−0.0025 (6)
N4	0.0340 (7)	0.0220 (6)	0.0418 (8)	−0.0020 (5)	−0.0016 (6)	0.0017 (6)
O1	0.0688 (10)	0.0210 (6)	0.0624 (9)	−0.0018 (6)	−0.0002 (7)	0.0037 (6)
O2	0.0654 (9)	0.0384 (7)	0.0371 (6)	−0.0033 (6)	0.0075 (6)	0.0023 (6)
O3	0.0279 (6)	0.0759 (10)	0.0468 (7)	0.0022 (6)	0.0057 (5)	0.0226 (7)
S1	0.0468 (3)	0.0340 (2)	0.0444 (2)	−0.00253 (18)	0.00230 (19)	−0.00687 (18)

Geometric parameters (Å, º) top

N4—H4B	0.85 (3)	C11—N2	1.379 (2)
C1—C6	1.383 (3)	C12—N3	1.469 (2)
C1—C2	1.387 (3)	C12—H12A	0.96
C1—H1	0.93	C12—H12B	0.96
C2—C3	1.379 (3)	C12—H12C	0.96
C2—H2	0.93	C13—O2	1.229 (2)
C3—C4	1.378 (4)	C13—N3	1.413 (2)
C3—H3	0.93	C13—C14	1.427 (2)
C4—C5	1.383 (3)	C14—C15	1.514 (2)
C4—H4	0.93	C15—N4	1.468 (2)
C5—C6	1.392 (3)	C15—C16	1.524 (2)
C5—H5	0.93	C15—H15	0.98
C6—C7	1.510 (3)	C16—C17	1.386 (2)
C7—S1	1.822 (2)	C16—C21	1.407 (2)
C7—H7A	0.97	C17—C18	1.388 (3)
C7—H7B	0.97	C17—H17	0.93
C8—N1	1.313 (2)	C18—C19	1.377 (3)
C8—N4	1.334 (2)	C18—H18	0.93
C8—S1	1.7596 (17)	C19—C20	1.381 (3)
C9—C14	1.362 (2)	C19—H19	0.93
C9—N1	1.372 (2)	C20—C21	1.393 (3)
C9—N2	1.3908 (19)	C20—H20	0.93
C10—N2	1.469 (2)	C21—O3	1.359 (2)
C10—H10A	0.96	C22—O3	1.431 (2)
C10—H10B	0.96	C22—H22A	0.96
C10—H10C	0.96	C22—H22B	0.96
C11—O1	1.227 (2)	C22—H22C	0.96
C11—N3	1.373 (2)

C6—C1—C2	121.20 (19)	N3—C13—C14	115.02 (14)
C6—C1—H1	119.4	C9—C14—C13	121.24 (14)
C2—C1—H1	119.4	C9—C14—C15	120.24 (14)
C3—C2—C1	120.1 (2)	C13—C14—C15	118.45 (14)
C3—C2—H2	120	N4—C15—C14	107.61 (13)
C1—C2—H2	120	N4—C15—C16	111.66 (13)
C4—C3—C2	119.4 (2)	C14—C15—C16	116.28 (13)
C4—C3—H3	120.3	N4—C15—H15	106.9
C2—C3—H3	120.3	C14—C15—H15	106.9
C3—C4—C5	120.4 (2)	C16—C15—H15	106.9
C3—C4—H4	119.8	C17—C16—C21	118.14 (15)
C5—C4—H4	119.8	C17—C16—C15	119.01 (14)
C4—C5—C6	120.9 (2)	C21—C16—C15	122.79 (14)
C4—C5—H5	119.5	C16—C17—C18	122.16 (17)
C6—C5—H5	119.5	C16—C17—H17	118.9
C1—C6—C5	117.99 (19)	C18—C17—H17	118.9
C1—C6—C7	121.56 (17)	C19—C18—C17	118.85 (18)
C5—C6—C7	120.45 (18)	C19—C18—H18	120.6
C6—C7—S1	113.99 (13)	C17—C18—H18	120.6
C6—C7—H7A	108.8	C18—C19—C20	120.64 (18)
S1—C7—H7A	108.8	C18—C19—H19	119.7
C6—C7—H7B	108.8	C20—C19—H19	119.7
S1—C7—H7B	108.8	C19—C20—C21	120.48 (19)
H7A—C7—H7B	107.6	C19—C20—H20	119.8
N1—C8—N4	125.81 (15)	C21—C20—H20	119.8
N1—C8—S1	119.63 (13)	O3—C21—C20	124.34 (17)
N4—C8—S1	114.52 (12)	O3—C21—C16	115.97 (15)
C14—C9—N1	125.32 (14)	C20—C21—C16	119.68 (17)
C14—C9—N2	120.04 (15)	O3—C22—H22A	109.5
N1—C9—N2	114.64 (14)	O3—C22—H22B	109.5
N2—C10—H10A	109.5	H22A—C22—H22B	109.5
N2—C10—H10B	109.5	O3—C22—H22C	109.5
H10A—C10—H10B	109.5	H22A—C22—H22C	109.5
N2—C10—H10C	109.5	H22B—C22—H22C	109.5
H10A—C10—H10C	109.5	C8—N1—C9	114.65 (14)
H10B—C10—H10C	109.5	C11—N2—C9	121.68 (14)
O1—C11—N3	121.48 (17)	C11—N2—C10	117.34 (14)
O1—C11—N2	121.47 (17)	C9—N2—C10	120.98 (14)
N3—C11—N2	117.05 (14)	C11—N3—C13	124.39 (14)
N3—C12—H12A	109.5	C11—N3—C12	117.56 (15)
N3—C12—H12B	109.5	C13—N3—C12	118.05 (15)
H12A—C12—H12B	109.5	C8—N4—C15	122.81 (14)
N3—C12—H12C	109.5	C8—N4—H4B	120.9 (16)
H12A—C12—H12C	109.5	C15—N4—H4B	114.5 (16)
H12B—C12—H12C	109.5	C21—O3—C22	117.82 (16)
O2—C13—N3	119.99 (16)	C8—S1—C7	102.25 (9)
O2—C13—C14	124.99 (16)

C6—C1—C2—C3	−0.4 (3)	C17—C16—C21—O3	178.46 (16)
C1—C2—C3—C4	0.3 (3)	C15—C16—C21—O3	−4.6 (3)
C2—C3—C4—C5	−0.2 (4)	C17—C16—C21—C20	−2.5 (3)
C3—C4—C5—C6	0.2 (4)	C15—C16—C21—C20	174.39 (17)
C2—C1—C6—C5	0.4 (3)	N4—C8—N1—C9	−1.1 (2)
C2—C1—C6—C7	−179.27 (18)	S1—C8—N1—C9	−178.71 (11)
C4—C5—C6—C1	−0.2 (3)	C14—C9—N1—C8	−7.4 (2)
C4—C5—C6—C7	179.4 (2)	N2—C9—N1—C8	172.47 (14)
C1—C6—C7—S1	100.2 (2)	O1—C11—N2—C9	−174.13 (16)
C5—C6—C7—S1	−79.5 (2)	N3—C11—N2—C9	6.3 (2)
N1—C9—C14—C13	176.78 (15)	O1—C11—N2—C10	5.0 (2)
N2—C9—C14—C13	−3.1 (2)	N3—C11—N2—C10	−174.62 (14)
N1—C9—C14—C15	−0.1 (2)	C14—C9—N2—C11	−4.1 (2)
N2—C9—C14—C15	−179.98 (13)	N1—C9—N2—C11	175.99 (14)
O2—C13—C14—C9	−172.94 (17)	C14—C9—N2—C10	176.78 (15)
N3—C13—C14—C9	7.4 (2)	N1—C9—N2—C10	−3.1 (2)
O2—C13—C14—C15	4.0 (2)	O1—C11—N3—C13	178.99 (17)
N3—C13—C14—C15	−175.67 (14)	N2—C11—N3—C13	−1.4 (2)
C9—C14—C15—N4	13.62 (19)	O1—C11—N3—C12	−0.7 (3)
C13—C14—C15—N4	−163.38 (13)	N2—C11—N3—C12	178.94 (16)
C9—C14—C15—C16	−112.44 (17)	O2—C13—N3—C11	175.12 (16)
C13—C14—C15—C16	70.56 (19)	C14—C13—N3—C11	−5.2 (2)
N4—C15—C16—C17	124.18 (16)	O2—C13—N3—C12	−5.2 (2)
C14—C15—C16—C17	−111.82 (17)	C14—C13—N3—C12	174.47 (15)
N4—C15—C16—C21	−52.7 (2)	N1—C8—N4—C15	17.5 (2)
C14—C15—C16—C21	71.3 (2)	S1—C8—N4—C15	−164.81 (11)
C21—C16—C17—C18	1.3 (3)	C14—C15—N4—C8	−21.9 (2)
C15—C16—C17—C18	−175.73 (17)	C16—C15—N4—C8	106.81 (17)
C16—C17—C18—C19	0.4 (3)	C20—C21—O3—C22	1.3 (3)
C17—C18—C19—C20	−1.0 (3)	C16—C21—O3—C22	−179.8 (2)
C18—C19—C20—C21	−0.3 (4)	N1—C8—S1—C7	−5.17 (15)
C19—C20—C21—O3	−179.0 (2)	N4—C8—S1—C7	176.99 (12)
C19—C20—C21—C16	2.1 (3)	C6—C7—S1—C8	−84.81 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4B···O1ⁱ	0.85 (3)	2.02 (3)	2.836 (2)	161 (2)

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

Experimental details

Crystal data
Chemical formula	C₂₂H₂₂N₄O₃S
M_r	422.51
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	294
a, b, c (Å)	10.9216 (9), 8.8528 (5), 20.7263 (15)
β (°)	90.638 (6)
V (Å³)	2003.8 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.4 × 0.3 × 0.05

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1998)
T_min, T_max	0.928, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	23191, 5394, 4510
R_int	0.063
(sin θ/λ)_max (Å⁻¹)	0.687

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.135, 1.15
No. of reflections	5394
No. of parameters	278
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.25

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXTL (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4B···O1ⁱ	0.85 (3)	2.02 (3)	2.836 (2)	161 (2)

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

Acknowledgements

AB is grateful to the Islamic Azad University, Dorood Branch, for financial support.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Devi, I., Kumar, B. S. D. & Bhuyan, P. J. (2003). Tetrahedron Lett. 44, 8307–8310. Web of Science CrossRef CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Quiroga, J., Insuasty, H., Insuasty, B., Abonia, R., Cobo, J., Sanchez, A. & Nogueras, M. (2002). Tetrahedron, 58, 4873–4877. Web of Science CrossRef CAS Google Scholar
Sharma, P., Rane, N. & Gurram, V. K. (2004). Bioorg. Med. Chem. Lett. 14, 4185–4190. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1998). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

7-(Benzyl­sulfan­yl)-5-(2-meth­oxy­phen­yl)-1,3-di­methyl-5,6-di­hydro­pyrimido[4,5-d]pyrimidine-2,4(1H,3H)-dione

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

7-(Benzylsulfanyl)-5-(2-methoxyphenyl)-1,3-dimethyl-5,6-dihydropyrimido[4,5-d]pyrimidine-2,4(1H,3H)-dione