1,4-Bis[(1H-pyrazol-1-yl)meth-yl]benzene dihydrate.

The asymmetric unit of the title compound, C(14)H(14)N(4)·2H(2)O consists of two half-mol-ecules of the main mol-ecule, each situated on an inversion center, and two mol-ecules of water. One-dimensional chains of water mol-ecules are built up by O-H⋯O hydrogen bonds which are then linked with the main mol-ecule via O-H⋯N hydrogen bonds, forming a two-dimensional supra-molecular network in the ac plane.

Related literature

For background and the synthesis, see: Chang et al. (1993 ▶). For similar structures, see: Bourne et al. (2006 ▶).

Experimental

Crystal data

C14H14N4·2H2O

M = 274.32

Monoclinic,

a = 4.680 (2) Å

b = 18.640 (8) Å

c = 16.974 (10) Å

β = 91.15 (2)°

V = 1480.6 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 291 K

0.29 × 0.27 × 0.19 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.956, T max = 0.984

14065 measured reflections

3361 independent reflections

1735 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.123

S = 1.00

3361 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.13 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); 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: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809007521/fl2236sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809007521/fl2236Isup2.hkl

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

C14H14N4·2H2O	F(000) = 584
Mr = 274.32	Dx = 1.231 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8012 reflections
a = 4.680 (2) Å	θ = 6.5–54.9°
b = 18.640 (8) Å	µ = 0.09 mm−1
c = 16.974 (10) Å	T = 291 K
β = 91.15 (2)°	Block, colorless
V = 1480.6 (13) Å3	0.29 × 0.27 × 0.19 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	3361 independent reflections
Radiation source: fine-focus sealed tube	1735 reflections with I > 2σ(I)
graphite	Rint = 0.050
ω scan	θmax = 27.5°, θmin = 3.3°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −6→5
Tmin = 0.956, Tmax = 0.984	k = −23→24
14065 measured reflections	l = −22→22

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0547P)2] where P = (Fo2 + 2Fc2)/3
3361 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.13 e Å−3

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.

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 > σ(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	0.8625 (5)	0.35411 (10)	0.69781 (13)	0.0727 (6)
H1	0.7584	0.3209	0.6680	0.087*
C2	1.0682 (5)	0.33893 (11)	0.75233 (13)	0.0784 (6)
H2	1.1345	0.2939	0.7677	0.094*
C3	1.1572 (4)	0.40427 (12)	0.77993 (12)	0.0737 (6)
H3	1.2983	0.4104	0.8187	0.088*
C4	0.6675 (4)	0.46818 (11)	0.63845 (12)	0.0709 (6)
H4	0.6093	0.5124	0.6635	0.085*
H5	0.4963	0.4419	0.6231	0.085*
C5	0.8366 (3)	0.48549 (9)	0.56601 (11)	0.0551 (4)
C6	0.8351 (4)	0.43987 (10)	0.50232 (12)	0.0642 (5)
H6	0.7232	0.3987	0.5034	0.077*
C7	1.0049 (4)	0.54625 (9)	0.56293 (11)	0.0622 (5)
H7	1.0099	0.5779	0.6053	0.075*
C8	0.5827 (4)	0.27680 (10)	−0.07594 (13)	0.0724 (6)
H8	0.6642	0.2909	−0.1230	0.087*
C9	0.3835 (5)	0.22438 (10)	−0.06711 (15)	0.0776 (6)
H9	0.3016	0.1955	−0.1061	0.093*
C10	0.3302 (4)	0.22347 (9)	0.01191 (14)	0.0706 (6)
H10	0.2015	0.1925	0.0354	0.085*
C11	0.8187 (4)	0.36625 (9)	0.01523 (13)	0.0663 (5)
H11	0.9808	0.3674	−0.0195	0.080*
H12	0.8916	0.3612	0.0688	0.080*
C12	0.6550 (3)	0.43624 (8)	0.00771 (11)	0.0527 (4)
C13	0.6725 (4)	0.47764 (9)	−0.05894 (11)	0.0616 (5)
H13	0.7898	0.4630	−0.0995	0.074*
C14	0.4809 (4)	0.45945 (9)	0.06678 (11)	0.0624 (5)
H14	0.4663	0.4324	0.1126	0.075*
N1	0.8358 (3)	0.42535 (8)	0.69450 (8)	0.0559 (4)
N2	1.0191 (3)	0.45779 (8)	0.74505 (9)	0.0660 (4)
N3	0.6401 (3)	0.30445 (7)	−0.00459 (10)	0.0579 (4)
N4	0.4843 (3)	0.27223 (7)	0.05120 (10)	0.0638 (4)
O1	0.4928 (3)	0.31462 (7)	0.21740 (9)	0.0847 (4)
H15	0.4939	0.3031	0.1690	0.127*
H16	0.3374	0.3373	0.2238	0.127*
O2	0.9966 (3)	0.38581 (8)	0.24291 (10)	0.1062 (6)
H17	0.9746	0.4311	0.2421	0.159*
H18	0.8329	0.3663	0.2386	0.159*

	U11	U22	U33	U12	U13	U23
C1	0.0920 (14)	0.0568 (11)	0.0693 (14)	−0.0064 (10)	0.0027 (12)	0.0032 (10)
C2	0.0967 (15)	0.0713 (13)	0.0674 (14)	0.0235 (12)	0.0093 (12)	0.0138 (11)
C3	0.0689 (12)	0.0959 (16)	0.0562 (12)	0.0135 (12)	−0.0021 (10)	0.0092 (11)
C4	0.0529 (10)	0.0895 (13)	0.0704 (14)	0.0117 (9)	0.0054 (10)	0.0187 (11)
C5	0.0413 (9)	0.0633 (10)	0.0605 (12)	0.0094 (8)	−0.0013 (8)	0.0145 (9)
C6	0.0646 (11)	0.0599 (10)	0.0679 (13)	−0.0089 (9)	−0.0060 (10)	0.0122 (10)
C7	0.0708 (11)	0.0571 (10)	0.0587 (12)	0.0052 (9)	−0.0026 (10)	0.0019 (9)
C8	0.0854 (14)	0.0656 (12)	0.0664 (15)	0.0127 (11)	0.0027 (11)	0.0025 (10)
C9	0.0921 (15)	0.0559 (11)	0.0839 (18)	0.0042 (11)	−0.0177 (13)	−0.0075 (11)
C10	0.0695 (12)	0.0487 (10)	0.0935 (18)	−0.0009 (9)	0.0001 (12)	0.0009 (10)
C11	0.0505 (10)	0.0544 (10)	0.0936 (16)	0.0012 (8)	−0.0073 (10)	0.0040 (10)
C12	0.0423 (8)	0.0491 (9)	0.0665 (12)	−0.0049 (7)	−0.0047 (8)	0.0034 (8)
C13	0.0599 (10)	0.0607 (11)	0.0646 (13)	0.0022 (8)	0.0130 (9)	0.0007 (9)
C14	0.0708 (11)	0.0570 (10)	0.0596 (12)	0.0019 (9)	0.0029 (10)	0.0135 (9)
N1	0.0495 (8)	0.0641 (9)	0.0543 (9)	0.0008 (7)	0.0061 (7)	0.0091 (7)
N2	0.0680 (9)	0.0699 (9)	0.0601 (10)	−0.0009 (8)	0.0042 (8)	−0.0023 (8)
N3	0.0561 (8)	0.0491 (7)	0.0682 (11)	0.0080 (7)	−0.0015 (8)	0.0022 (8)
N4	0.0669 (9)	0.0537 (8)	0.0709 (11)	0.0047 (8)	0.0043 (8)	0.0025 (8)
O1	0.0878 (9)	0.0774 (9)	0.0887 (11)	−0.0004 (7)	−0.0012 (8)	0.0027 (8)
O2	0.0867 (10)	0.0885 (10)	0.1433 (16)	0.0021 (8)	0.0031 (10)	−0.0361 (10)

C1—N1	1.335 (2)	C9—C10	1.369 (3)
C1—C2	1.352 (3)	C9—H9	0.9300
C1—H1	0.9300	C10—N4	1.331 (2)
C2—C3	1.367 (3)	C10—H10	0.9300
C2—H2	0.9300	C11—N3	1.459 (2)
C3—N2	1.322 (2)	C11—C12	1.517 (2)
C3—H3	0.9300	C11—H11	0.9700
C4—N1	1.460 (2)	C11—H12	0.9700
C4—C5	1.510 (2)	C12—C13	1.373 (2)
C4—H4	0.9700	C12—C14	1.375 (2)
C4—H5	0.9700	C13—C14ii	1.380 (2)
C5—C6	1.375 (3)	C13—H13	0.9300
C5—C7	1.381 (2)	C14—C13ii	1.380 (2)
C6—C7i	1.374 (3)	C14—H14	0.9300
C6—H6	0.9300	N1—N2	1.345 (2)
C7—C6i	1.374 (3)	N3—N4	1.348 (2)
C7—H7	0.9300	O1—H15	0.8500
C8—N3	1.339 (2)	O1—H16	0.8500
C8—C9	1.361 (3)	O2—H17	0.8500
C8—H8	0.9300	O2—H18	0.8500
N1—C1—C2	107.56 (18)	C10—C9—H9	127.6
N1—C1—H1	126.2	N4—C10—C9	112.01 (18)
C2—C1—H1	126.2	N4—C10—H10	124.0
C1—C2—C3	104.84 (18)	C9—C10—H10	124.0
C1—C2—H2	127.6	N3—C11—C12	111.94 (14)
C3—C2—H2	127.6	N3—C11—H11	109.2
N2—C3—C2	112.08 (19)	C12—C11—H11	109.2
N2—C3—H3	124.0	N3—C11—H12	109.2
C2—C3—H3	124.0	C12—C11—H12	109.2
N1—C4—C5	111.25 (14)	H11—C11—H12	107.9
N1—C4—H4	109.4	C13—C12—C14	118.04 (16)
C5—C4—H4	109.4	C13—C12—C11	120.95 (17)
N1—C4—H5	109.4	C14—C12—C11	121.00 (16)
C5—C4—H5	109.4	C12—C13—C14ii	121.16 (16)
H4—C4—H5	108.0	C12—C13—H13	119.4
C6—C5—C7	118.11 (16)	C14ii—C13—H13	119.4
C6—C5—C4	120.89 (17)	C12—C14—C13ii	120.80 (16)
C7—C5—C4	120.97 (18)	C12—C14—H14	119.6
C7i—C6—C5	121.54 (17)	C13ii—C14—H14	119.6
C7i—C6—H6	119.2	C1—N1—N2	111.26 (16)
C5—C6—H6	119.2	C1—N1—C4	128.31 (17)
C6i—C7—C5	120.36 (17)	N2—N1—C4	119.92 (15)
C6i—C7—H7	119.8	C3—N2—N1	104.26 (16)
C5—C7—H7	119.8	C8—N3—N4	111.25 (16)
N3—C8—C9	107.6 (2)	C8—N3—C11	128.06 (17)
N3—C8—H8	126.2	N4—N3—C11	120.37 (16)
C9—C8—H8	126.2	C10—N4—N3	104.34 (16)
C8—C9—C10	104.80 (19)	H15—O1—H16	105.7
C8—C9—H9	127.6	H17—O2—H18	108.3

D—H···A	D—H	H···A	D···A	D—H···A
O1—H15···N4	0.85	2.08	2.929 (3)	178
O1—H16···O2iii	0.85	1.87	2.717 (2)	177
O2—H17···N2i	0.85	2.08	2.923 (2)	170
O2—H18···O1	0.85	1.89	2.733 (2)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H15⋯N4	0.85	2.08	2.929 (3)	178
O1—H16⋯O2i	0.85	1.87	2.717 (2)	177
O2—H17⋯N2ii	0.85	2.08	2.923 (2)	170
O2—H18⋯O1	0.85	1.89	2.733 (2)	172

Symmetry codes: (i) ; (ii) .