7-(Benzyl-sulfan-yl)-5-(2-methoxy-phen-yl)-1,3-dimethyl-5,6-dihydro-pyrimido[4,5-d]pyrimidine-2,4(1H,3H)-dione.

In the mol-ecule of the title compound, C(22)H(22)N(4)O(3)S, 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, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules.

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 = 422.51

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.135

S = 1.15

5394 reflections

278 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.25 e Å−3

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 ▶).

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

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

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

C22H22N4O3S	F000 = 888
Mr = 422.51	Dx = 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 = 2.1–29.3º
b = 8.8528 (5) Å	µ = 0.20 mm−1
c = 20.7263 (15) Å	T = 294 (2) K
β = 90.638 (6)º	Plate, colorless
V = 2003.8 (2) Å3	0.4 × 0.3 × 0.05 mm
Z = 4

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

Refinement on F2	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0538P)2 + 0.6815P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.055	(Δ/σ)max = 0.038
wR(F2) = 0.135	Δρmax = 0.32 e Å−3
S = 1.15	Δρmin = −0.25 e Å−3
5394 reflections	Extinction correction: none
278 parameters

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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)

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) .