4,4',6,6'-Tetra-methyl-2,2'-bipyrimidine hexa-hydrate.

In the title compound, C(12)H(14)N(4)·6H(2)O, the two pyrimidine rings make a dihedral angle of 5.285 (6)°. Inter-molecular O-H⋯O hydrogen bonds link the six water mol-ecules, generating edge-fused four-, five- or six-membered ring motifs and forming two-dimensional sheets. The sheets are stabilized by the formation of O-H⋯N hydrogen bonds between the water mol-ecules and the bipyrimidine mol-ecules, resulting in a three-dimensional network.

Related literature

For 2,2′-bipyrimidine and its derivatives, see: Ji et al. (2000 ▶); Baumann et al. (1998 ▶). For hydrogen-bonded water clusters, see: Buck & Huisken (2000 ▶); Lakshminarayanan et al. (2006 ▶). For water–water inter­actions in bulk water or ice, see: Zhang et al. (2005 ▶). For bond lengths and angles, see: Berg et al. (2002 ▶). For the preparation of the compound by the Ullmann coupling method, see: Vlad & Horvath (2002 ▶).

Experimental

Crystal data

C12H14N4·6H2O

M = 322.37

Triclinic,

a = 6.8622 (19) Å

b = 11.098 (3) Å

c = 11.750 (3) Å

α = 98.233 (3)°

β = 91.774 (4)°

γ = 102.599 (4)°

V = 862.4 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.41 × 0.31 × 0.21 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.961, T max = 0.980

6492 measured reflections

3196 independent reflections

2026 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.148

S = 1.04

3196 reflections

204 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.15 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: SHELXS97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809010095/at2743sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010095/at2743Isup2.hkl

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

C12H14N4·6H2O	Z = 2
Mr = 322.37	F(000) = 348
Triclinic, P1	Dx = 1.241 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8622 (19) Å	Cell parameters from 1270 reflections
b = 11.098 (3) Å	θ = 1.0–1.0°
c = 11.750 (3) Å	µ = 0.10 mm−1
α = 98.233 (3)°	T = 296 K
β = 91.774 (4)°	Block, colourless
γ = 102.599 (4)°	0.41 × 0.31 × 0.21 mm
V = 862.4 (4) Å3

Bruker APEXII CCD area-detector diffractometer	3196 independent reflections
Radiation source: fine-focus sealed tube	2026 reflections with I > 2σ(I)
graphite	Rint = 0.023
φ and ω scans	θmax = 25.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.961, Tmax = 0.980	k = −13→13
6492 measured reflections	l = −14→14

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047	H-atom parameters constrained
wR(F2) = 0.148	w = 1/[σ2(Fo2) + (0.074P)2 + 0.0388P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
3196 reflections	Δρmax = 0.23 e Å−3
204 parameters	Δρmin = −0.15 e Å−3
0 restraints	Extinction correction: SHELXS97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.045 (6)

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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR andgoodness of fit S are based on F2, conventional R-factors R are basedon F, with F set to zero for negative F2. The threshold expression ofF2 > σ(F2) is used only for calculating R-factors(gt) etc. and isnot relevant to the choice of reflections for refinement. R-factors basedon 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
O1	1.0078 (2)	0.66049 (15)	0.38126 (13)	0.0642 (5)
H1W	0.9576	0.6341	0.3142	0.096*
H2W	0.9194	0.6501	0.4285	0.096*
O2	0.4638 (2)	0.32153 (14)	0.82784 (13)	0.0576 (5)
H3W	0.3978	0.2491	0.8284	0.086*
H4W	0.5591	0.3379	0.8787	0.086*
O3	0.1279 (3)	0.42962 (14)	0.85957 (13)	0.0620 (5)
H5W	0.0432	0.3909	0.8985	0.093*
H6W	0.2226	0.3952	0.8493	0.093*
O4	0.6255 (3)	0.40256 (16)	0.62491 (14)	0.0672 (5)
H7W	0.5777	0.3790	0.6846	0.101*
H8W	0.7336	0.3788	0.6155	0.101*
O5	0.2031 (2)	0.66114 (14)	1.01180 (14)	0.0624 (5)
H9W	0.2119	0.7281	0.9869	0.094*
H10W	0.1897	0.6013	0.9586	0.094*
O6	0.7043 (3)	0.63916 (16)	0.54052 (14)	0.0705 (5)
H11W	0.6024	0.6411	0.5015	0.106*
H12W	0.6844	0.5744	0.5710	0.106*
N1	0.2840 (3)	0.14305 (16)	0.99505 (14)	0.0417 (4)
N2	0.2855 (3)	0.04691 (15)	0.77127 (13)	0.0417 (4)
N3	0.2336 (2)	−0.15832 (15)	0.82104 (14)	0.0403 (4)
N4	0.2327 (2)	−0.06158 (15)	1.04606 (14)	0.0407 (4)
C1	0.1870 (4)	−0.1038 (2)	1.24073 (18)	0.0559 (6)
H1A	0.0530	−0.1535	1.2264	0.084*
H1B	0.2033	−0.0587	1.3178	0.084*
H1C	0.2801	−0.1572	1.2319	0.084*
C2	0.2256 (3)	−0.0134 (2)	1.15686 (17)	0.0414 (5)
C3	0.2480 (3)	0.1139 (2)	1.18979 (17)	0.0452 (5)
H3	0.2434	0.1471	1.2667	0.054*
C4	0.2775 (3)	0.19090 (19)	1.10592 (17)	0.0432 (5)
C5	0.3011 (4)	0.3293 (2)	1.1331 (2)	0.0632 (7)
H5A	0.4190	0.3704	1.1002	0.095*
H5B	0.3133	0.3543	1.2152	0.095*
H5C	0.1861	0.3522	1.1015	0.095*
C6	0.2612 (3)	0.01975 (18)	0.97125 (16)	0.0365 (5)
C7	0.2621 (3)	−0.03399 (18)	0.84670 (16)	0.0363 (5)
C8	0.1946 (4)	−0.3443 (2)	0.6791 (2)	0.0617 (7)
H8A	0.3139	−0.3691	0.7017	0.093*
H8B	0.1661	−0.3685	0.5975	0.093*
H8C	0.0846	−0.3845	0.7189	0.093*
C9	0.2245 (3)	−0.20604 (19)	0.70895 (17)	0.0432 (5)
C10	0.2398 (3)	−0.1290 (2)	0.62551 (18)	0.0496 (6)
H10	0.2286	−0.1625	0.5477	0.060*
C11	0.2719 (3)	−0.00161 (19)	0.65939 (17)	0.0449 (5)
C12	0.2935 (4)	0.0891 (2)	0.57525 (19)	0.0644 (7)
H12A	0.1977	0.1402	0.5887	0.097*
H12B	0.2705	0.0442	0.4982	0.097*
H12C	0.4262	0.1413	0.5849	0.097*

	U11	U22	U33	U12	U13	U23
O1	0.0689 (12)	0.0708 (11)	0.0513 (10)	0.0119 (9)	0.0050 (8)	0.0098 (8)
O2	0.0637 (11)	0.0499 (9)	0.0589 (10)	0.0082 (8)	0.0062 (8)	0.0138 (8)
O3	0.0686 (11)	0.0632 (11)	0.0583 (10)	0.0187 (8)	0.0111 (8)	0.0151 (8)
O4	0.0691 (12)	0.0825 (12)	0.0556 (10)	0.0191 (9)	0.0074 (8)	0.0251 (9)
O5	0.0743 (12)	0.0495 (9)	0.0617 (10)	0.0089 (8)	0.0045 (9)	0.0101 (8)
O6	0.0698 (12)	0.0794 (12)	0.0626 (11)	0.0096 (9)	0.0030 (9)	0.0231 (9)
N1	0.0440 (10)	0.0440 (10)	0.0355 (9)	0.0073 (8)	0.0036 (8)	0.0043 (8)
N2	0.0505 (11)	0.0413 (10)	0.0332 (9)	0.0100 (8)	0.0055 (8)	0.0052 (8)
N3	0.0430 (10)	0.0412 (10)	0.0365 (9)	0.0090 (8)	0.0047 (8)	0.0057 (8)
N4	0.0407 (10)	0.0472 (10)	0.0349 (9)	0.0105 (8)	0.0049 (7)	0.0076 (8)
C1	0.0706 (16)	0.0596 (15)	0.0415 (13)	0.0177 (12)	0.0136 (11)	0.0141 (11)
C2	0.0357 (11)	0.0537 (13)	0.0351 (11)	0.0096 (10)	0.0038 (9)	0.0082 (9)
C3	0.0448 (13)	0.0571 (14)	0.0328 (11)	0.0124 (10)	0.0058 (9)	0.0023 (10)
C4	0.0422 (12)	0.0469 (12)	0.0387 (12)	0.0091 (10)	0.0017 (9)	0.0021 (9)
C5	0.0879 (19)	0.0528 (15)	0.0461 (14)	0.0161 (13)	0.0047 (13)	−0.0024 (11)
C6	0.0326 (11)	0.0438 (12)	0.0330 (11)	0.0083 (9)	0.0031 (8)	0.0060 (9)
C7	0.0317 (10)	0.0417 (11)	0.0356 (11)	0.0079 (9)	0.0035 (8)	0.0067 (9)
C8	0.0899 (19)	0.0485 (14)	0.0475 (14)	0.0197 (13)	0.0058 (13)	0.0033 (11)
C9	0.0462 (13)	0.0427 (12)	0.0397 (12)	0.0088 (9)	0.0047 (9)	0.0044 (9)
C10	0.0640 (15)	0.0482 (13)	0.0322 (11)	0.0072 (11)	0.0025 (10)	0.0002 (10)
C11	0.0523 (13)	0.0462 (13)	0.0361 (11)	0.0098 (10)	0.0050 (10)	0.0078 (9)
C12	0.103 (2)	0.0525 (15)	0.0378 (13)	0.0139 (14)	0.0069 (13)	0.0121 (11)

O1—H1W	0.8358	C1—H1B	0.9600
O1—H2W	0.8355	C1—H1C	0.9600
O2—H3W	0.8334	C2—C3	1.383 (3)
O2—H4W	0.8431	C3—C4	1.386 (3)
O3—H5W	0.8342	C3—H3	0.9300
O3—H6W	0.8269	C4—C5	1.496 (3)
O4—H7W	0.8351	C5—H5A	0.9600
O4—H8W	0.8443	C5—H5B	0.9600
O5—H9W	0.8278	C5—H5C	0.9600
O5—H10W	0.8314	C6—C7	1.500 (3)
O6—H11W	0.8302	C8—C9	1.492 (3)
O6—H12W	0.8353	C8—H8A	0.9600
N1—C6	1.330 (2)	C8—H8B	0.9600
N1—C4	1.340 (3)	C8—H8C	0.9600
N2—C7	1.338 (2)	C9—C10	1.383 (3)
N2—C11	1.340 (3)	C10—C11	1.379 (3)
N3—C7	1.339 (2)	C10—H10	0.9300
N3—C9	1.341 (3)	C11—C12	1.498 (3)
N4—C6	1.337 (2)	C12—H12A	0.9600
N4—C2	1.341 (3)	C12—H12B	0.9600
C1—C2	1.493 (3)	C12—H12C	0.9600
C1—H1A	0.9600
H1W—O1—H2W	110.2	H5A—C5—H5C	109.5
H3W—O2—H4W	109.0	H5B—C5—H5C	109.5
H5W—O3—H6W	111.2	N1—C6—N4	126.97 (18)
H7W—O4—H8W	108.4	N1—C6—C7	116.44 (17)
H9W—O5—H10W	111.6	N4—C6—C7	116.57 (18)
H11W—O6—H12W	109.9	N3—C7—N2	126.13 (18)
C6—N1—C4	116.54 (17)	N3—C7—C6	117.13 (17)
C7—N2—C11	116.80 (17)	N2—C7—C6	116.70 (17)
C7—N3—C9	116.70 (17)	C9—C8—H8A	109.5
C6—N4—C2	116.31 (18)	C9—C8—H8B	109.5
C2—C1—H1A	109.5	H8A—C8—H8B	109.5
C2—C1—H1B	109.5	C9—C8—H8C	109.5
H1A—C1—H1B	109.5	H8A—C8—H8C	109.5
C2—C1—H1C	109.5	H8B—C8—H8C	109.5
H1A—C1—H1C	109.5	N3—C9—C10	120.62 (19)
H1B—C1—H1C	109.5	N3—C9—C8	117.30 (18)
N4—C2—C3	120.80 (18)	C10—C9—C8	122.07 (19)
N4—C2—C1	116.81 (19)	C11—C10—C9	118.96 (19)
C3—C2—C1	122.37 (19)	C11—C10—H10	120.5
C2—C3—C4	118.69 (19)	C9—C10—H10	120.5
C2—C3—H3	120.7	N2—C11—C10	120.71 (18)
C4—C3—H3	120.7	N2—C11—C12	116.59 (19)
N1—C4—C3	120.68 (19)	C10—C11—C12	122.71 (19)
N1—C4—C5	116.81 (19)	C11—C12—H12A	109.5
C3—C4—C5	122.50 (19)	C11—C12—H12B	109.5
C4—C5—H5A	109.5	H12A—C12—H12B	109.5
C4—C5—H5B	109.5	C11—C12—H12C	109.5
H5A—C5—H5B	109.5	H12A—C12—H12C	109.5
C4—C5—H5C	109.5	H12B—C12—H12C	109.5
C6—N4—C2—C3	−0.3 (3)	C11—N2—C7—N3	2.5 (3)
C6—N4—C2—C1	178.04 (18)	C11—N2—C7—C6	−175.32 (18)
N4—C2—C3—C4	0.2 (3)	N1—C6—C7—N3	−178.13 (16)
C1—C2—C3—C4	−178.1 (2)	N4—C6—C7—N3	0.3 (3)
C6—N1—C4—C3	−0.1 (3)	N1—C6—C7—N2	−0.1 (3)
C6—N1—C4—C5	−179.45 (19)	N4—C6—C7—N2	178.33 (16)
C2—C3—C4—N1	0.1 (3)	C7—N3—C9—C10	−1.4 (3)
C2—C3—C4—C5	179.3 (2)	C7—N3—C9—C8	179.46 (19)
C4—N1—C6—N4	0.0 (3)	N3—C9—C10—C11	2.3 (3)
C4—N1—C6—C7	178.16 (17)	C8—C9—C10—C11	−178.5 (2)
C2—N4—C6—N1	0.3 (3)	C7—N2—C11—C10	−1.4 (3)
C2—N4—C6—C7	−177.94 (17)	C7—N2—C11—C12	178.63 (19)
C9—N3—C7—N2	−1.1 (3)	C9—C10—C11—N2	−0.9 (3)
C9—N3—C7—C6	176.71 (17)	C9—C10—C11—C12	179.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1W···O3i	0.84	2.08	2.914 (2)	172
O1—H2W···O6	0.84	2.00	2.837 (2)	175
O2—H3W···N2	0.83	2.20	2.995 (2)	158
O2—H3W···N1	0.83	2.49	3.083 (2)	129
O2—H4W···O5ii	0.84	2.04	2.872 (2)	167
O3—H5W···O5iii	0.83	2.04	2.847 (2)	163
O3—H6W···O2	0.83	2.01	2.832 (2)	177
O4—H7W···O2	0.84	2.01	2.841 (2)	180
O4—H8W···O1iv	0.84	1.92	2.755 (2)	171
O5—H9W···N4v	0.83	2.31	3.007 (2)	142
O5—H9W···N3v	0.83	2.46	3.196 (2)	149
O5—H10W···O3	0.83	2.04	2.849 (2)	166
O6—H11W···O4i	0.83	2.05	2.851 (2)	162
O6—H12W···O4	0.84	2.06	2.886 (2)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1W⋯O3i	0.84	2.08	2.914 (2)	172
O1—H2W⋯O6	0.84	2.00	2.837 (2)	175
O2—H3W⋯N2	0.83	2.20	2.995 (2)	158
O2—H3W⋯N1	0.83	2.49	3.083 (2)	129
O2—H4W⋯O5ii	0.84	2.04	2.872 (2)	167
O3—H5W⋯O5iii	0.83	2.04	2.847 (2)	163
O3—H6W⋯O2	0.83	2.01	2.832 (2)	177
O4—H7W⋯O2	0.84	2.01	2.841 (2)	180
O4—H8W⋯O1iv	0.84	1.92	2.755 (2)	171
O5—H9W⋯N4v	0.83	2.31	3.007 (2)	142
O5—H9W⋯N3v	0.83	2.46	3.196 (2)	149
O5—H10W⋯O3	0.83	2.04	2.849 (2)	166
O6—H11W⋯O4i	0.83	2.05	2.851 (2)	162
O6—H12W⋯O4	0.84	2.06	2.886 (2)	173

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