4-Hy-droxy-5-(2-meth-oxy-phen-oxy)-2,2'-bipyrimidin-6(5H)-one dihydrate.

The title compound, C15H12N4O4·2H2O, crystallizes with two independent water mol-ecules in the asymmetric unit. The dihedral angles between the mean planes of the benzene and pyrimidine rings and that of the pyrimidin-4-one ring are 85.1 (9) and 82.1 (1)°, respectively. The mean plane of the pyrimidine ring is twisted by 12.8 (8)° from that of the pyrimidin-4-one ring. The dihedral angles between the benzene ring and the mean planes of the pyrimidine and pyrimidin-4-one rings are 85.1 (9) and 82.1 (1)°, respectively.In the crystal, N-H⋯O, O-H⋯N and O-H⋯O hydrogen bonds involving both water mol-ecules are present; these link the mol-ecules into a two-dimensional network parallel to (010). In addition, weak C-H⋯π and π-π [centroid-centroid distance = 3.6183 (8) Å] inter-actions occur.

Related literature

For substituted pyrimidine-2,4-diones as good reversible inhibitors of thymidine phospho­rylase, see: Baker & Rzeszotarki (1967 ▶). For the use of 2,2′-bi­pyrimidine as a ligand in inorganic and organometallic chemistry, see: Hunziker & Ludi (1977 ▶); Fabrice et al. (2008 ▶). For related structures, see: El-Brollosy et al. (2012 ▶); Fun et al. (2009 ▶); Kaur et al. (2013 ▶); Ren et al. (2011 ▶); Trilleras et al. (2009 ▶).

Experimental

Crystal data

C15H12N4O4·2H2O

M = 348.32

Monoclinic,

a = 9.5817 (3) Å

b = 13.9439 (3) Å

c = 12.4804 (4) Å

β = 109.832 (3)°

V = 1568.55 (8) Å3

Z = 4

Cu Kα radiation

μ = 0.99 mm−1

T = 173 K

0.45 × 0.32 × 0.24 mm

Data collection

Agilent Xcalibur (Eos, Gemini) diffractometer

Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶) T min = 0.876, T max = 1.000

9840 measured reflections

3070 independent reflections

2789 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.115

S = 1.03

3070 reflections

252 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012 ▶); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ▶); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813028900/bt6940sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813028900/bt6940Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813028900/bt6940Isup3.cml

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

C15H12N4O4·2H2O	F(000) = 728
Mr = 348.32	Dx = 1.475 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 9.5817 (3) Å	Cell parameters from 4761 reflections
b = 13.9439 (3) Å	θ = 3.2–72.3°
c = 12.4804 (4) Å	µ = 0.99 mm−1
β = 109.832 (3)°	T = 173 K
V = 1568.55 (8) Å3	Irregular, colourless
Z = 4	0.45 × 0.32 × 0.24 mm

Agilent Xcalibur (Eos, Gemini) diffractometer	3070 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2789 reflections with I > 2σ(I)
Detector resolution: 16.0416 pixels mm-1	Rint = 0.040
ω scans	θmax = 72.5°, θmin = 4.9°
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	h = −11→11
Tmin = 0.876, Tmax = 1.000	k = −17→13
9840 measured reflections	l = −15→14

Refinement on F2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.041	w = 1/[σ2(Fo2) + (0.0697P)2 + 0.4106P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.115	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.31 e Å−3
3070 reflections	Δρmin = −0.26 e Å−3
252 parameters	Extinction correction: SHELXL2012 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.0118 (8)
Primary atom site location: structure-invariant direct methods

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.

	x	y	z	Uiso*/Ueq
O1	0.66810 (10)	0.07758 (7)	0.72585 (8)	0.0234 (2)
O2	0.83857 (10)	0.17796 (7)	0.64227 (8)	0.0218 (2)
O3	1.14014 (11)	0.20971 (7)	0.71581 (8)	0.0261 (3)
H3	1.235 (3)	0.2265 (17)	0.727 (2)	0.059 (7)*
O4	0.67224 (10)	0.27899 (8)	0.44713 (8)	0.0284 (3)
N1	0.99634 (13)	0.47988 (8)	0.33822 (10)	0.0233 (3)
N2	1.24321 (12)	0.42848 (8)	0.43964 (10)	0.0228 (3)
N3	1.12057 (12)	0.31273 (8)	0.56724 (9)	0.0199 (3)
N4	0.88527 (12)	0.34237 (8)	0.43264 (10)	0.0214 (3)
C1	1.09611 (14)	0.42507 (9)	0.41329 (11)	0.0195 (3)
C2	1.29246 (15)	0.49577 (11)	0.38523 (12)	0.0268 (3)
H2	1.3965	0.5022	0.4023	0.032*
C3	1.19918 (17)	0.55649 (10)	0.30517 (12)	0.0284 (3)
H3A	1.2366	0.6040	0.2675	0.034*
C4	1.04900 (16)	0.54475 (10)	0.28272 (12)	0.0261 (3)
H4A	0.9812	0.5838	0.2264	0.031*
C5	1.03430 (14)	0.35477 (9)	0.47561 (11)	0.0189 (3)
C6	0.80944 (14)	0.28493 (9)	0.48529 (11)	0.0205 (3)
C7	0.90348 (14)	0.23650 (9)	0.58376 (11)	0.0196 (3)
C8	1.05471 (14)	0.25246 (9)	0.62200 (11)	0.0198 (3)
C9	0.79005 (14)	0.08924 (9)	0.59160 (11)	0.0202 (3)
C10	0.82984 (16)	0.05252 (10)	0.50337 (12)	0.0255 (3)
H10	0.8894	0.0895	0.4715	0.031*
C11	0.78253 (18)	−0.03891 (11)	0.46092 (13)	0.0314 (3)
H11	0.8091	−0.0640	0.3997	0.038*
C12	0.69761 (19)	−0.09249 (11)	0.50761 (14)	0.0341 (4)
H12	0.6664	−0.1550	0.4792	0.041*
C13	0.65690 (17)	−0.05569 (11)	0.59662 (13)	0.0294 (3)
H13	0.5980	−0.0931	0.6285	0.035*
C14	0.70226 (14)	0.03557 (10)	0.63884 (11)	0.0211 (3)
C15	0.59236 (18)	0.01817 (12)	0.78172 (13)	0.0329 (4)
H15A	0.5822	0.0526	0.8472	0.049*
H15B	0.6492	−0.0409	0.8080	0.049*
H15C	0.4937	0.0021	0.7283	0.049*
O1W	0.50931 (13)	0.68034 (8)	0.41460 (10)	0.0335 (3)
O2W	0.41708 (12)	0.25759 (10)	0.25780 (10)	0.0385 (3)
H2WA	0.493 (3)	0.2699 (16)	0.316 (2)	0.049 (6)*
H2WB	0.445 (3)	0.2361 (16)	0.199 (2)	0.055 (6)*
H4	0.836 (2)	0.3704 (14)	0.3675 (18)	0.037 (5)*
H1WA	0.460 (3)	0.7048 (16)	0.455 (2)	0.050 (6)*
H1WB	0.592 (3)	0.6557 (17)	0.464 (2)	0.058 (7)*

	U11	U22	U33	U12	U13	U23
O1	0.0213 (5)	0.0276 (5)	0.0228 (5)	−0.0045 (4)	0.0095 (4)	−0.0001 (4)
O2	0.0242 (5)	0.0226 (5)	0.0198 (5)	−0.0055 (3)	0.0091 (4)	−0.0022 (3)
O3	0.0201 (5)	0.0306 (5)	0.0234 (5)	−0.0006 (4)	0.0017 (4)	0.0072 (4)
O4	0.0149 (5)	0.0421 (6)	0.0260 (5)	−0.0032 (4)	0.0041 (4)	0.0052 (4)
N1	0.0211 (6)	0.0246 (6)	0.0225 (6)	−0.0014 (4)	0.0051 (4)	0.0012 (4)
N2	0.0186 (6)	0.0276 (6)	0.0228 (6)	−0.0015 (4)	0.0080 (4)	−0.0011 (4)
N3	0.0162 (5)	0.0217 (6)	0.0207 (6)	−0.0004 (4)	0.0049 (4)	−0.0004 (4)
N4	0.0160 (5)	0.0271 (6)	0.0195 (6)	0.0000 (4)	0.0036 (4)	0.0034 (4)
C1	0.0191 (6)	0.0214 (6)	0.0181 (6)	−0.0020 (5)	0.0062 (5)	−0.0034 (5)
C2	0.0213 (7)	0.0352 (8)	0.0266 (7)	−0.0055 (5)	0.0115 (6)	−0.0021 (6)
C3	0.0341 (8)	0.0287 (7)	0.0249 (7)	−0.0079 (6)	0.0135 (6)	−0.0001 (5)
C4	0.0294 (7)	0.0245 (7)	0.0220 (7)	−0.0022 (5)	0.0056 (5)	0.0015 (5)
C5	0.0163 (6)	0.0202 (6)	0.0204 (6)	−0.0004 (4)	0.0064 (5)	−0.0028 (5)
C6	0.0169 (6)	0.0250 (7)	0.0196 (6)	−0.0029 (5)	0.0061 (5)	−0.0025 (5)
C7	0.0199 (7)	0.0204 (6)	0.0193 (6)	−0.0031 (5)	0.0076 (5)	−0.0016 (5)
C8	0.0196 (6)	0.0197 (6)	0.0188 (6)	0.0010 (5)	0.0047 (5)	−0.0012 (5)
C9	0.0176 (6)	0.0214 (6)	0.0187 (6)	−0.0010 (5)	0.0022 (5)	0.0001 (5)
C10	0.0268 (7)	0.0274 (7)	0.0236 (7)	−0.0028 (5)	0.0101 (5)	−0.0012 (5)
C11	0.0385 (8)	0.0304 (8)	0.0259 (7)	−0.0003 (6)	0.0117 (6)	−0.0065 (6)
C12	0.0416 (9)	0.0246 (7)	0.0333 (8)	−0.0079 (6)	0.0090 (7)	−0.0081 (6)
C13	0.0302 (7)	0.0274 (7)	0.0297 (7)	−0.0087 (6)	0.0090 (6)	−0.0007 (6)
C14	0.0176 (6)	0.0258 (7)	0.0179 (6)	−0.0007 (5)	0.0034 (5)	0.0008 (5)
C15	0.0335 (8)	0.0399 (8)	0.0299 (8)	−0.0119 (6)	0.0167 (6)	0.0000 (6)
O1W	0.0237 (6)	0.0415 (6)	0.0361 (6)	0.0028 (4)	0.0114 (5)	0.0038 (5)
O2W	0.0189 (5)	0.0652 (8)	0.0275 (6)	−0.0042 (5)	0.0028 (5)	−0.0095 (5)

O1—C14	1.3676 (16)	C4—H4A	0.9500
O1—C15	1.4292 (16)	C6—C7	1.4237 (19)
O2—C7	1.3765 (15)	C7—C8	1.3812 (18)
O2—C9	1.3952 (16)	C9—C10	1.3802 (19)
O3—H3	0.91 (3)	C9—C14	1.3970 (18)
O3—C8	1.3212 (16)	C10—H10	0.9500
O4—C6	1.2398 (16)	C10—C11	1.396 (2)
N1—C1	1.3297 (18)	C11—H11	0.9500
N1—C4	1.3378 (18)	C11—C12	1.372 (2)
N2—C1	1.3351 (17)	C12—H12	0.9500
N2—C2	1.3347 (18)	C12—C13	1.394 (2)
N3—C5	1.3013 (17)	C13—H13	0.9500
N3—C8	1.3653 (17)	C13—C14	1.390 (2)
N4—C5	1.3554 (16)	C15—H15A	0.9800
N4—C6	1.3874 (17)	C15—H15B	0.9800
N4—H4	0.88 (2)	C15—H15C	0.9800
C1—C5	1.4930 (17)	O1W—H1WA	0.87 (2)
C2—H2	0.9500	O1W—H1WB	0.89 (3)
C2—C3	1.381 (2)	O2W—H2WA	0.86 (2)
C3—H3A	0.9500	O2W—H2WB	0.91 (3)
C3—C4	1.379 (2)
C14—O1—C15	115.91 (11)	O3—C8—N3	117.94 (12)
C7—O2—C9	115.24 (10)	O3—C8—C7	119.70 (12)
C8—O3—H3	108.2 (15)	N3—C8—C7	122.35 (12)
C1—N1—C4	116.50 (12)	O2—C9—C14	116.07 (11)
C2—N2—C1	115.19 (12)	C10—C9—O2	123.42 (12)
C5—N3—C8	116.97 (11)	C10—C9—C14	120.45 (12)
C5—N4—C6	122.48 (11)	C9—C10—H10	120.0
C5—N4—H4	118.2 (13)	C9—C10—C11	119.98 (13)
C6—N4—H4	119.3 (13)	C11—C10—H10	120.0
N1—C1—N2	126.84 (12)	C10—C11—H11	120.0
N1—C1—C5	115.28 (11)	C12—C11—C10	119.95 (13)
N2—C1—C5	117.86 (11)	C12—C11—H11	120.0
N2—C2—H2	118.5	C11—C12—H12	119.8
N2—C2—C3	123.04 (13)	C11—C12—C13	120.31 (14)
C3—C2—H2	118.5	C13—C12—H12	119.8
C2—C3—H3A	121.7	C12—C13—H13	119.9
C4—C3—C2	116.66 (13)	C14—C13—C12	120.22 (13)
C4—C3—H3A	121.7	C14—C13—H13	119.9
N1—C4—C3	121.72 (13)	O1—C14—C9	116.50 (12)
N1—C4—H4A	119.1	O1—C14—C13	124.41 (12)
C3—C4—H4A	119.1	C13—C14—C9	119.09 (12)
N3—C5—N4	124.06 (12)	O1—C15—H15A	109.5
N3—C5—C1	120.51 (11)	O1—C15—H15B	109.5
N4—C5—C1	115.37 (11)	O1—C15—H15C	109.5
O4—C6—N4	120.94 (12)	H15A—C15—H15B	109.5
O4—C6—C7	125.30 (12)	H15A—C15—H15C	109.5
N4—C6—C7	113.76 (11)	H15B—C15—H15C	109.5
O2—C7—C6	118.15 (11)	H1WA—O1W—H1WB	107 (2)
O2—C7—C8	121.47 (12)	H2WA—O2W—H2WB	111 (2)
C8—C7—C6	120.29 (12)
O2—C7—C8—O3	1.07 (19)	C5—N4—C6—O4	176.19 (12)
O2—C7—C8—N3	−177.80 (11)	C5—N4—C6—C7	−3.53 (18)
O2—C9—C10—C11	176.86 (13)	C6—N4—C5—N3	2.0 (2)
O2—C9—C14—O1	2.85 (17)	C6—N4—C5—C1	−175.25 (11)
O2—C9—C14—C13	−176.50 (12)	C6—C7—C8—O3	177.58 (12)
O4—C6—C7—O2	0.1 (2)	C6—C7—C8—N3	−1.29 (19)
O4—C6—C7—C8	−176.55 (13)	C7—O2—C9—C10	13.23 (18)
N1—C1—C5—N3	−164.82 (12)	C7—O2—C9—C14	−169.66 (11)
N1—C1—C5—N4	12.53 (16)	C8—N3—C5—N4	0.20 (19)
N2—C1—C5—N3	13.60 (18)	C8—N3—C5—C1	177.32 (11)
N2—C1—C5—N4	−169.04 (11)	C9—O2—C7—C6	76.38 (14)
N2—C2—C3—C4	0.0 (2)	C9—O2—C7—C8	−107.04 (13)
N4—C6—C7—O2	179.77 (10)	C9—C10—C11—C12	−0.6 (2)
N4—C6—C7—C8	3.15 (18)	C10—C9—C14—O1	−179.95 (12)
C1—N1—C4—C3	−2.3 (2)	C10—C9—C14—C13	0.7 (2)
C1—N2—C2—C3	−1.5 (2)	C10—C11—C12—C13	0.7 (2)
C2—N2—C1—N1	1.32 (19)	C11—C12—C13—C14	−0.1 (2)
C2—N2—C1—C5	−176.90 (11)	C12—C13—C14—O1	−179.89 (13)
C2—C3—C4—N1	2.0 (2)	C12—C13—C14—C9	−0.6 (2)
C4—N1—C1—N2	0.5 (2)	C14—C9—C10—C11	−0.1 (2)
C4—N1—C1—C5	178.78 (11)	C15—O1—C14—C9	−173.34 (12)
C5—N3—C8—O3	−179.40 (11)	C15—O1—C14—C13	5.96 (19)
C5—N3—C8—C7	−0.51 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2Wi	0.91 (3)	1.67 (3)	2.5651 (15)	172 (2)
N4—H4···O1ii	0.88 (2)	2.08 (2)	2.9313 (15)	163.6 (18)
O1W—H1WA···O4iii	0.87 (2)	2.05 (2)	2.8917 (16)	163 (2)
O1W—H1WB···N2iv	0.89 (3)	2.01 (3)	2.8823 (16)	167 (2)
O2W—H2WA···O4	0.86 (2)	1.93 (3)	2.7803 (15)	172 (2)
O2W—H2WB···O1Wv	0.91 (3)	1.80 (3)	2.7050 (17)	173 (2)
C4—H4A···Cg3vi	0.95	2.82	3.4083 (16)	121

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C9–C14 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2W i	0.91 (3)	1.67 (3)	2.5651 (15)	172 (2)
N4—H4⋯O1ii	0.88 (2)	2.08 (2)	2.9313 (15)	163.6 (18)
O1W—H1WA⋯O4iii	0.87 (2)	2.05 (2)	2.8917 (16)	163 (2)
O1W—H1WB⋯N2iv	0.89 (3)	2.01 (3)	2.8823 (16)	167 (2)
O2W—H2WA⋯O4	0.86 (2)	1.93 (3)	2.7803 (15)	172 (2)
O2W—H2WB⋯O1W v	0.91 (3)	1.80 (3)	2.7050 (17)	173 (2)
C4—H4A⋯Cg3vi	0.95	2.82	3.4083 (16)	121

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .