4,5,8a-Triphenyl-perhydro-pyrimido[4,5-d]pyrimidine-2,7-dione monohydrate.

The title compound, C(24)H(22)N(4)O(2)·H(2)O, was synthesized by the trimethyl-chloro-silane-catalysed reaction between urea, benzaldehyde and acetophenone. The organic mol-ecule comprises two fused tetra-hydro-pyrimidinone rings with phenyl substituents at the 4- and 5-positions on the tetra-hydro-pyrimidinone rings and a third phenyl substituent at the ring junction 8-position. The 4- and 5-substituted phenyl rings are inclined at a dihedral angle of 22.72 (11)° to one another and make angles of 47.95 (7) and 65.76 (7)° with the third phenyl substituent. In the crystal structure, inter-molecular N-H⋯O contacts link pyrimido[4,5-d]pyrimidine mol-ecules into centrosymmetric dimers. Additional N-H⋯O and O-H⋯O hydrogen bonds involving the water mol-ecule generate a three-dimensional network.

Related literature

For the therapeutic and pharmacological properties of pyrimidopyrimidines, see: Agarwal et al. (2005 ▶); Gangjee et al. (2005 ▶). For the synthesis of related compounds, see: Shi et al. (2007 ▶); Zhu et al. (2005 ▶). For reference bond-length data, see Allen et al. (1987 ▶).

Experimental

Crystal data

C24H22N4O2·H2O

M = 416.47

Monoclinic,

a = 11.3150 (2) Å

b = 17.4935 (3) Å

c = 10.5794 (2) Å

β = 94.731 (1)°

V = 2086.94 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.30 × 0.15 × 0.15 mm

Data collection

Bruker APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.977, T max = 0.981

18167 measured reflections

3768 independent reflections

2835 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.110

S = 1.04

3768 reflections

305 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810019525/sj2783sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810019525/sj2783Isup2.hkl

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

C24H22N4O2·H2O	F(000) = 880.0
Mr = 416.47	Dx = 1.326 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5618 reflections
a = 11.3150 (2) Å	θ = 2.3–23.5°
b = 17.4935 (3) Å	µ = 0.09 mm−1
c = 10.5794 (2) Å	T = 298 K
β = 94.731 (1)°	Block, colourless
V = 2086.94 (6) Å3	0.30 × 0.15 × 0.15 mm
Z = 4

Bruker APEXII area-detector diffractometer	3768 independent reflections
Radiation source: fine-focus sealed tube	2835 reflections with I > 2σ(I)
graphite	Rint = 0.035
φ and ω scans	θmax = 25.2°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −13→10
Tmin = 0.977, Tmax = 0.981	k = −20→20
18167 measured reflections	l = −12→12

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.110	w = 1/[σ2(Fo2) + (0.0452P)2 + 0.5316P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
3768 reflections	Δρmax = 0.25 e Å−3
305 parameters	Δρmin = −0.20 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0066 (11)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
C1	0.36015 (14)	0.01198 (9)	0.26268 (15)	0.0391 (4)
H7	0.4045	0.0419	0.3291	0.047*
C2	0.23967 (14)	0.12916 (9)	0.20681 (14)	0.0373 (4)
C3	0.39979 (15)	0.08608 (9)	0.07274 (15)	0.0425 (4)
C4	0.23326 (14)	0.04423 (9)	0.24437 (14)	0.0372 (4)
H8	0.1903	0.0165	0.1743	0.045*
C5	0.16508 (15)	0.03406 (9)	0.36401 (14)	0.0419 (4)
H6	0.1853	−0.0169	0.3975	0.050*
C6	0.26422 (15)	0.15513 (10)	0.43883 (15)	0.0436 (4)
C7	0.05756 (18)	0.12622 (12)	0.05276 (18)	0.0632 (6)
H19	0.0897	0.0833	0.0166	0.076*
C8	−0.0509 (2)	0.15353 (16)	0.0041 (2)	0.0809 (7)
H20	−0.0919	0.1286	−0.0637	0.097*
C9	−0.0985 (2)	0.21711 (15)	0.0550 (2)	0.0752 (7)
H21	−0.1719	0.2354	0.0225	0.090*
C10	−0.03787 (19)	0.25315 (12)	0.1531 (2)	0.0709 (6)
H22	−0.0697	0.2968	0.1871	0.085*
C11	0.07081 (17)	0.22610 (10)	0.20371 (19)	0.0544 (5)
H23	0.1112	0.2516	0.2713	0.065*
C12	0.11932 (15)	0.16153 (9)	0.15439 (14)	0.0401 (4)
C13	0.36784 (14)	−0.07141 (9)	0.30018 (16)	0.0411 (4)
C14	0.33752 (17)	−0.12905 (10)	0.2150 (2)	0.0562 (5)
H9	0.3092	−0.1171	0.1324	0.067*
C15	0.3491 (2)	−0.20481 (12)	0.2519 (3)	0.0792 (7)
H12	0.3274	−0.2433	0.1940	0.095*
C16	0.3920 (2)	−0.22366 (14)	0.3727 (3)	0.0882 (9)
H13	0.4006	−0.2747	0.3964	0.106*
C17	0.42204 (19)	−0.16715 (15)	0.4581 (3)	0.0788 (7)
H11	0.4512	−0.1795	0.5403	0.095*
C18	0.40914 (17)	−0.09161 (12)	0.42245 (19)	0.0594 (5)
H10	0.4286	−0.0534	0.4817	0.071*
C19	−0.0248 (2)	−0.02385 (13)	0.26918 (19)	0.0676 (6)
H14	0.0207	−0.0640	0.2423	0.081*
C20	0.03073 (16)	0.03569 (10)	0.33765 (15)	0.0461 (4)
C21	−0.03979 (18)	0.09298 (11)	0.38007 (19)	0.0597 (5)
H18	−0.0056	0.1327	0.4288	0.072*
C22	−0.1615 (2)	0.09177 (16)	0.3504 (3)	0.0835 (8)
H17	−0.2078	0.1310	0.3792	0.100*
C23	−0.2142 (2)	0.0342 (2)	0.2799 (3)	0.0919 (9)
H16	−0.2956	0.0347	0.2589	0.110*
C24	−0.1464 (2)	−0.02467 (18)	0.2401 (2)	0.0863 (8)
H15	−0.1819	−0.0650	0.1939	0.104*
N1	0.41552 (14)	0.02324 (9)	0.14448 (14)	0.0510 (4)
N2	0.32026 (12)	0.13779 (8)	0.10666 (13)	0.0413 (4)
N3	0.28885 (13)	0.17073 (8)	0.31879 (12)	0.0438 (4)
N4	0.20999 (14)	0.08804 (9)	0.45970 (14)	0.0523 (4)
O1	0.45673 (11)	0.09641 (7)	−0.02172 (11)	0.0588 (4)
O2	0.29450 (12)	0.19940 (7)	0.52711 (11)	0.0574 (4)
O3	0.33428 (16)	0.17446 (9)	0.78386 (16)	0.0704 (4)
H4	0.3149 (17)	0.2203 (12)	0.3069 (18)	0.065 (6)*
H24	0.3154 (16)	0.1796 (11)	0.0634 (17)	0.053 (5)*
H5	0.4604 (17)	−0.0120 (11)	0.1161 (18)	0.059 (6)*
H3	0.1959 (18)	0.0816 (12)	0.538 (2)	0.068 (6)*
H2	0.348 (2)	0.1705 (15)	0.705 (3)	0.105 (10)*
H1	0.396 (3)	0.1510 (18)	0.834 (3)	0.134 (12)*

	U11	U22	U33	U12	U13	U23
C1	0.0430 (10)	0.0364 (9)	0.0385 (8)	0.0023 (7)	0.0078 (7)	0.0025 (7)
C2	0.0451 (10)	0.0350 (9)	0.0329 (8)	0.0041 (7)	0.0102 (7)	−0.0003 (7)
C3	0.0454 (10)	0.0415 (10)	0.0419 (9)	0.0079 (8)	0.0128 (8)	0.0058 (7)
C4	0.0441 (10)	0.0349 (9)	0.0337 (8)	0.0029 (7)	0.0087 (7)	−0.0011 (7)
C5	0.0520 (11)	0.0367 (9)	0.0385 (9)	0.0022 (8)	0.0129 (8)	0.0026 (7)
C6	0.0462 (10)	0.0479 (10)	0.0366 (9)	0.0083 (8)	0.0032 (7)	−0.0050 (8)
C7	0.0619 (13)	0.0773 (14)	0.0495 (11)	0.0218 (11)	−0.0001 (10)	−0.0104 (10)
C8	0.0638 (15)	0.112 (2)	0.0636 (13)	0.0229 (14)	−0.0117 (11)	−0.0120 (13)
C9	0.0529 (13)	0.0919 (17)	0.0806 (15)	0.0226 (12)	0.0045 (12)	0.0150 (14)
C10	0.0604 (14)	0.0555 (13)	0.0983 (17)	0.0202 (11)	0.0158 (12)	0.0005 (12)
C11	0.0513 (11)	0.0439 (10)	0.0688 (12)	0.0075 (9)	0.0096 (9)	−0.0036 (9)
C12	0.0429 (10)	0.0420 (9)	0.0368 (8)	0.0048 (7)	0.0118 (7)	0.0049 (7)
C13	0.0367 (9)	0.0379 (9)	0.0501 (10)	0.0040 (7)	0.0120 (7)	0.0069 (8)
C14	0.0589 (12)	0.0446 (11)	0.0673 (12)	−0.0003 (9)	0.0175 (10)	−0.0022 (9)
C15	0.0836 (17)	0.0423 (12)	0.117 (2)	−0.0061 (11)	0.0391 (15)	−0.0081 (13)
C16	0.0692 (16)	0.0487 (14)	0.153 (3)	0.0128 (12)	0.0479 (17)	0.0400 (17)
C17	0.0558 (14)	0.0805 (17)	0.1011 (18)	0.0085 (12)	0.0119 (12)	0.0540 (15)
C18	0.0563 (12)	0.0601 (12)	0.0611 (12)	−0.0037 (10)	0.0009 (10)	0.0207 (10)
C19	0.0715 (15)	0.0681 (14)	0.0666 (13)	−0.0176 (11)	0.0253 (11)	−0.0107 (11)
C20	0.0529 (11)	0.0454 (10)	0.0422 (9)	−0.0032 (8)	0.0172 (8)	0.0054 (8)
C21	0.0588 (13)	0.0535 (12)	0.0699 (12)	0.0029 (10)	0.0246 (10)	0.0060 (10)
C22	0.0590 (15)	0.0851 (18)	0.111 (2)	0.0151 (13)	0.0339 (14)	0.0259 (16)
C23	0.0548 (15)	0.132 (3)	0.0900 (18)	−0.0157 (17)	0.0133 (14)	0.0343 (18)
C24	0.0707 (17)	0.120 (2)	0.0700 (15)	−0.0420 (16)	0.0173 (13)	−0.0067 (14)
N1	0.0580 (10)	0.0447 (9)	0.0541 (9)	0.0191 (8)	0.0274 (8)	0.0148 (7)
N2	0.0495 (9)	0.0351 (8)	0.0415 (8)	0.0091 (7)	0.0166 (6)	0.0092 (6)
N3	0.0564 (9)	0.0365 (8)	0.0389 (8)	−0.0015 (7)	0.0056 (6)	−0.0019 (6)
N4	0.0663 (11)	0.0598 (10)	0.0321 (8)	−0.0081 (8)	0.0121 (7)	−0.0015 (7)
O1	0.0683 (9)	0.0564 (8)	0.0566 (8)	0.0213 (6)	0.0352 (7)	0.0193 (6)
O2	0.0704 (9)	0.0578 (8)	0.0431 (7)	0.0036 (7)	−0.0007 (6)	−0.0156 (6)
O3	0.0936 (12)	0.0656 (10)	0.0516 (9)	0.0181 (8)	0.0030 (8)	0.0027 (7)

C1—N1	1.458 (2)	C11—H23	0.9300
C1—C13	1.512 (2)	C13—C14	1.377 (2)
C1—C4	1.540 (2)	C13—C18	1.384 (2)
C1—H7	0.9800	C14—C15	1.385 (3)
C2—N3	1.461 (2)	C14—H9	0.9300
C2—N2	1.462 (2)	C15—C16	1.370 (4)
C2—C12	1.536 (2)	C15—H12	0.9300
C2—C4	1.541 (2)	C16—C17	1.363 (4)
C3—O1	1.2460 (18)	C16—H13	0.9300
C3—N1	1.339 (2)	C17—C18	1.379 (3)
C3—N2	1.345 (2)	C17—H11	0.9300
C4—C5	1.546 (2)	C18—H10	0.9300
C4—H8	0.9800	C19—C24	1.385 (3)
C5—N4	1.446 (2)	C19—C20	1.389 (3)
C5—C20	1.523 (2)	C19—H14	0.9300
C5—H6	0.9800	C20—C21	1.379 (3)
C6—O2	1.2397 (19)	C21—C22	1.387 (3)
C6—N3	1.350 (2)	C21—H18	0.9300
C6—N4	1.351 (2)	C22—C23	1.362 (4)
C7—C8	1.376 (3)	C22—H17	0.9300
C7—C12	1.379 (2)	C23—C24	1.370 (4)
C7—H19	0.9300	C23—H16	0.9300
C8—C9	1.366 (3)	C24—H15	0.9300
C8—H20	0.9300	N1—H5	0.87 (2)
C9—C10	1.351 (3)	N2—H24	0.862 (19)
C9—H21	0.9300	N3—H4	0.93 (2)
C10—C11	1.384 (3)	N4—H3	0.86 (2)
C10—H22	0.9300	O3—H2	0.87 (3)
C11—C12	1.377 (2)	O3—H1	0.94 (3)
N1—C1—C13	109.63 (13)	C14—C13—C1	121.94 (16)
N1—C1—C4	107.75 (12)	C18—C13—C1	119.93 (16)
C13—C1—C4	114.79 (13)	C13—C14—C15	120.3 (2)
N1—C1—H7	108.2	C13—C14—H9	119.9
C13—C1—H7	108.2	C15—C14—H9	119.9
C4—C1—H7	108.2	C16—C15—C14	120.8 (2)
N3—C2—N2	108.53 (13)	C16—C15—H12	119.6
N3—C2—C12	112.11 (12)	C14—C15—H12	119.6
N2—C2—C12	106.73 (12)	C17—C16—C15	119.6 (2)
N3—C2—C4	107.08 (12)	C17—C16—H13	120.2
N2—C2—C4	109.39 (12)	C15—C16—H13	120.2
C12—C2—C4	112.92 (13)	C16—C17—C18	119.9 (2)
O1—C3—N1	121.35 (15)	C16—C17—H11	120.0
O1—C3—N2	121.18 (15)	C18—C17—H11	120.0
N1—C3—N2	117.47 (14)	C17—C18—C13	121.4 (2)
C1—C4—C2	108.80 (13)	C17—C18—H10	119.3
C1—C4—C5	112.20 (12)	C13—C18—H10	119.3
C2—C4—C5	111.06 (12)	C24—C19—C20	121.4 (2)
C1—C4—H8	108.2	C24—C19—H14	119.3
C2—C4—H8	108.2	C20—C19—H14	119.3
C5—C4—H8	108.2	C21—C20—C19	117.78 (19)
N4—C5—C20	113.82 (14)	C21—C20—C5	123.35 (17)
N4—C5—C4	109.13 (13)	C19—C20—C5	118.87 (17)
C20—C5—C4	113.95 (13)	C20—C21—C22	120.4 (2)
N4—C5—H6	106.5	C20—C21—H18	119.8
C20—C5—H6	106.5	C22—C21—H18	119.8
C4—C5—H6	106.5	C23—C22—C21	121.2 (2)
O2—C6—N3	121.10 (17)	C23—C22—H17	119.4
O2—C6—N4	121.38 (15)	C21—C22—H17	119.4
N3—C6—N4	117.46 (15)	C22—C23—C24	119.5 (2)
C8—C7—C12	121.00 (19)	C22—C23—H16	120.2
C8—C7—H19	119.5	C24—C23—H16	120.2
C12—C7—H19	119.5	C23—C24—C19	119.7 (2)
C9—C8—C7	120.2 (2)	C23—C24—H15	120.2
C9—C8—H20	119.9	C19—C24—H15	120.2
C7—C8—H20	119.9	C3—N1—C1	123.42 (14)
C10—C9—C8	119.4 (2)	C3—N1—H5	116.2 (13)
C10—C9—H21	120.3	C1—N1—H5	120.4 (13)
C8—C9—H21	120.3	C3—N2—C2	126.51 (14)
C9—C10—C11	121.1 (2)	C3—N2—H24	116.3 (12)
C9—C10—H22	119.5	C2—N2—H24	117.1 (12)
C11—C10—H22	119.5	C6—N3—C2	124.60 (15)
C12—C11—C10	120.20 (19)	C6—N3—H4	114.1 (12)
C12—C11—H23	119.9	C2—N3—H4	117.4 (12)
C10—C11—H23	119.9	C6—N4—C5	126.24 (14)
C11—C12—C7	118.07 (17)	C6—N4—H3	113.2 (14)
C11—C12—C2	122.34 (15)	C5—N4—H3	120.2 (14)
C7—C12—C2	119.58 (15)	H2—O3—H1	109 (3)
C14—C13—C18	118.12 (17)
N1—C1—C4—C2	−57.64 (16)	C14—C15—C16—C17	1.0 (3)
C13—C1—C4—C2	179.93 (13)	C15—C16—C17—C18	−0.1 (3)
N1—C1—C4—C5	179.05 (13)	C16—C17—C18—C13	−1.1 (3)
C13—C1—C4—C5	56.63 (18)	C14—C13—C18—C17	1.3 (3)
N3—C2—C4—C1	−70.43 (15)	C1—C13—C18—C17	−177.18 (17)
N2—C2—C4—C1	47.01 (16)	C24—C19—C20—C21	2.3 (3)
C12—C2—C4—C1	165.70 (12)	C24—C19—C20—C5	−178.68 (18)
N3—C2—C4—C5	53.55 (17)	N4—C5—C20—C21	12.8 (2)
N2—C2—C4—C5	170.99 (13)	C4—C5—C20—C21	−113.21 (18)
C12—C2—C4—C5	−70.32 (16)	N4—C5—C20—C19	−166.15 (15)
C1—C4—C5—N4	73.88 (17)	C4—C5—C20—C19	67.8 (2)
C2—C4—C5—N4	−48.15 (18)	C19—C20—C21—C22	−2.4 (3)
C1—C4—C5—C20	−157.68 (14)	C5—C20—C21—C22	178.66 (17)
C2—C4—C5—C20	80.30 (17)	C20—C21—C22—C23	0.4 (3)
C12—C7—C8—C9	0.9 (4)	C21—C22—C23—C24	1.6 (4)
C7—C8—C9—C10	0.4 (4)	C22—C23—C24—C19	−1.7 (4)
C8—C9—C10—C11	−0.9 (4)	C20—C19—C24—C23	−0.3 (3)
C9—C10—C11—C12	0.1 (3)	O1—C3—N1—C1	173.66 (17)
C10—C11—C12—C7	1.2 (3)	N2—C3—N1—C1	−6.2 (3)
C10—C11—C12—C2	179.89 (17)	C13—C1—N1—C3	164.44 (16)
C8—C7—C12—C11	−1.7 (3)	C4—C1—N1—C3	38.9 (2)
C8—C7—C12—C2	179.58 (19)	O1—C3—N2—C2	173.39 (16)
N3—C2—C12—C11	4.8 (2)	N1—C3—N2—C2	−6.7 (3)
N2—C2—C12—C11	−113.91 (17)	N3—C2—N2—C3	100.86 (18)
C4—C2—C12—C11	125.86 (16)	C12—C2—N2—C3	−138.12 (16)
N3—C2—C12—C7	−176.50 (16)	C4—C2—N2—C3	−15.7 (2)
N2—C2—C12—C7	64.79 (19)	O2—C6—N3—C2	−169.06 (15)
C4—C2—C12—C7	−55.4 (2)	N4—C6—N3—C2	13.7 (2)
N1—C1—C13—C14	−47.6 (2)	N2—C2—N3—C6	−155.76 (15)
C4—C1—C13—C14	73.77 (19)	C12—C2—N3—C6	86.60 (19)
N1—C1—C13—C18	130.74 (17)	C4—C2—N3—C6	−37.8 (2)
C4—C1—C13—C18	−107.85 (18)	O2—C6—N4—C5	176.39 (16)
C18—C13—C14—C15	−0.3 (3)	N3—C6—N4—C5	−6.4 (3)
C1—C13—C14—C15	178.08 (17)	C20—C5—N4—C6	−103.71 (19)
C13—C14—C15—C16	−0.8 (3)	C4—C5—N4—C6	24.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H5···O1i	0.87 (2)	2.05 (2)	2.9098 (19)	169.5 (18)
N2—H24···O2ii	0.862 (19)	2.16 (2)	2.9774 (19)	157.9 (16)
N3—H4···O3ii	0.93 (2)	1.87 (2)	2.787 (2)	168.1 (18)
O3—H1···O1iii	0.94 (3)	1.88 (3)	2.747 (2)	152 (3)
O3—H2···O2	0.87 (3)	1.99 (3)	2.751 (2)	146 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H5⋯O1i	0.87 (2)	2.05 (2)	2.9098 (19)	169.5 (18)
N2—H24⋯O2ii	0.862 (19)	2.16 (2)	2.9774 (19)	157.9 (16)
N3—H4⋯O3ii	0.93 (2)	1.87 (2)	2.787 (2)	168.1 (18)
O3—H1⋯O1iii	0.94 (3)	1.88 (3)	2.747 (2)	152 (3)
O3—H2⋯O2	0.87 (3)	1.99 (3)	2.751 (2)	146 (2)

Symmetry codes: (i) ; (ii) ; (iii) .