1,4-Bis{[2-(pyridin-2-yl)-1H-imidazol-1-yl]meth­yl}benzene dihydrate

In the title compound, C₂₄H₂₀N₆·2H₂O, the 1,4-bis­{[2-(pyridin-2-yl)-1H-imidazol-1-yl]meth­yl}benzene neutral mol­ecule lies on a centre of symmetry; the molecule is linked to the solvent water molecule via O—H...N hydrogen bonds, generating a two-dimensional supra­molecular layer parallel to (100).

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.040
• wR factor = 0.098
• Data-to-parameter ratio = 16.6

checkCIF/PLATON results

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Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C7     -   C8      ..       5.23 su

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          3

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

Metal-organic extended structures have attracted considerable interest in coordination chemistry and material science because of their intriguing structural diversities and potential applications in functional materials, nanotechnology and biological recognition (Ayyappan et al., 2002; Eddaoudi et al., 2001; Kitaura et al., 2002; Russell et al., 1997; Tao et al., 2000). Therefore, rational design and construction of coordination polymers with this potential diversity of architectures has become a particularly important subject. The key factor is the selection of the organic ligand, because it plays an important role in the formation of different metal-organic compounds. In this paper, we present a new organic N-donor ligand, (C₂₄H₂₀N₆)(H₂O)₂, (I).

Compound (I) is composed of L and solvent water molecules, in a 1:2 ratio: the main molecule lies onto a symmetry centre, thus rendering only half of it independent (Fig. 1). Interatomic bond distances and angles are normal. The L ligands are hydrogen bonded to the water molecules via O—H···N interactions, forming a two-dimensional supramolecular structure parallel to (100). (Table 1 andFig. 2).

Related literature

The related literatures, see: Ayyappan et al. (2002); Eddaoudi et al. (2001); Kitaura et al. (2002); Russell et al. (1997); Tao et al. (2000).

S2. Experimental

A mixture of 2-(2-pyridyl)imidazole (7.25 g, 50 mmol) and NaOH (2.00 g, 50 mmol) in DMSO (20 ml) was stirred at 60°C for 1 h, then 1,4-bis(chloromethyl)benzene (4.35 g, 25 mmol) was added. The mixture was cooled to room temperature after stirring at 60°C for 24 h, and then poured into 200 ml of water. A yellow solid of L formed immediately, which was isolated by filtration in 80% yield after drying in air. Crystals suitable for X-ray diffraction were recrystallized in 95% ethanol.

S3. Refinement

All H atoms on C atoms were poisitioned geometrically and refined as riding atoms, with C—H = 0.93 - 0.97 Å, and U_iso=1.2U_eq (C). The H atoms of water molecule were located in a difference Fourier map and then refined isotropically.

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. A view of the molecule of (I). Displacement ellipsoids are drawn at the 30% probability level. Symmetry code: (iii) 1 - x, -y, -z.
	Fig. 2. Ball-stick representation of the two-dimensional supramolecular layer of (I).

1,4-Bis{[2-(pyridin-2-yl)-1H-imidazol-1-yl]methyl}benzene dihydrate

Crystal data

C24H20N6·2H2O	Z = 2
Mr = 428.49	F(000) = 452
Monoclinic, P21/c	Dx = 1.328 Mg m^−3
Hall symbol: -P2ybc	Mo Kα radiation, λ = 0.71069 Å
a = 7.503 (2) Å	θ = 1.4–28.3°
b = 28.450 (2) Å	µ = 0.09 mm^−1
c = 5.030 (4) Å	T = 293 K
β = 93.572 (2)°	Block, colorless
V = 1071.6 (9) Å^3	0.40 × 0.38 × 0.36 mm

Data collection

Bruker APEX CCD area-detector diffractometer	2513 independent reflections
Radiation source: fine-focus sealed tube	1417 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
ω scans	θmax = 28.3°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→7
Tmin = 0.96, Tmax = 0.97	k = −21→37
6504 measured reflections	l = −5→6

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ^2(Fo^2) + (0.045P)^2] where P = (Fo^2 + 2Fc^2)/3
2513 reflections	(Δ/σ)max < 0.001
151 parameters	Δρmax = 0.15 e Å^−3
3 restraints	Δρmin = −0.18 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.9173 (2)	0.07266 (5)	0.5679 (3)	0.0547 (4)
H1	0.9156	0.0497	0.6992	0.066*
C2	1.0601 (2)	0.09773 (5)	0.4992 (3)	0.0576 (4)
H2	1.1749	0.0946	0.5781	0.069*
C3	0.83834 (18)	0.12158 (4)	0.2435 (2)	0.0419 (3)
C4	0.73301 (18)	0.14836 (4)	0.0402 (3)	0.0421 (3)
C5	0.81846 (19)	0.17646 (5)	−0.1371 (3)	0.0491 (4)
H5	0.9425	0.1781	−0.1297	0.059*
C6	0.7186 (2)	0.20188 (5)	−0.3232 (3)	0.0605 (4)
H6	0.7740	0.2207	−0.4447	0.073*
C7	0.5358 (2)	0.19924 (6)	−0.3287 (3)	0.0656 (5)
H7	0.4648	0.2164	−0.4518	0.079*
C8	0.4610 (2)	0.17053 (6)	−0.1468 (3)	0.0659 (5)
H8	0.3371	0.1687	−0.1511	0.079*
C9	0.59462 (18)	0.06872 (5)	0.4145 (3)	0.0500 (4)
H9A	0.5098	0.0945	0.4002	0.060*
H9B	0.5829	0.0536	0.5854	0.060*
C10	0.54828 (18)	0.03374 (4)	0.1959 (2)	0.0421 (3)
C11	0.66866 (18)	0.00005 (5)	0.1222 (3)	0.0486 (4)
H11	0.7837	−0.0002	0.2025	0.058*
C12	0.37921 (18)	0.03328 (5)	0.0689 (3)	0.0487 (4)
H12	0.2963	0.0558	0.1130	0.058*
N1	0.77573 (15)	0.08776 (4)	0.4063 (2)	0.0446 (3)
N2	1.01221 (15)	0.12840 (4)	0.2967 (2)	0.0514 (3)
N3	0.55510 (16)	0.14497 (4)	0.0368 (2)	0.0560 (3)
O1W	0.13387 (17)	0.27264 (4)	0.8409 (2)	0.0716 (3)
H1A	0.129 (2)	0.2590 (5)	0.685 (2)	0.107*
H1B	0.109 (2)	0.3018 (3)	0.811 (3)	0.107*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0708 (10)	0.0442 (8)	0.0481 (8)	0.0043 (8)	−0.0036 (8)	0.0046 (7)
C2	0.0562 (10)	0.0551 (9)	0.0599 (10)	0.0098 (8)	−0.0072 (8)	−0.0016 (8)
C3	0.0491 (9)	0.0356 (7)	0.0415 (7)	−0.0039 (6)	0.0051 (6)	−0.0037 (6)
C4	0.0503 (9)	0.0353 (7)	0.0406 (8)	−0.0004 (6)	0.0006 (6)	−0.0072 (6)
C5	0.0584 (9)	0.0443 (8)	0.0443 (8)	−0.0026 (7)	0.0017 (7)	−0.0010 (7)
C6	0.0864 (12)	0.0450 (9)	0.0495 (9)	0.0002 (8)	0.0002 (8)	0.0018 (7)
C7	0.0869 (13)	0.0510 (10)	0.0566 (10)	0.0121 (9)	−0.0148 (9)	−0.0015 (8)
C8	0.0549 (10)	0.0651 (11)	0.0757 (12)	0.0070 (8)	−0.0120 (8)	−0.0078 (10)
C9	0.0602 (9)	0.0452 (8)	0.0458 (8)	−0.0100 (7)	0.0121 (7)	−0.0021 (7)
C10	0.0519 (9)	0.0339 (7)	0.0413 (7)	−0.0065 (6)	0.0091 (6)	0.0023 (6)
C11	0.0487 (8)	0.0443 (8)	0.0526 (8)	−0.0032 (7)	0.0015 (7)	−0.0016 (7)
C12	0.0526 (9)	0.0404 (8)	0.0541 (9)	0.0018 (6)	0.0105 (7)	−0.0053 (7)
N1	0.0530 (7)	0.0379 (6)	0.0428 (6)	−0.0040 (5)	0.0019 (5)	−0.0016 (5)
N2	0.0487 (7)	0.0502 (7)	0.0549 (7)	−0.0010 (6)	0.0002 (6)	−0.0011 (6)
N3	0.0518 (8)	0.0544 (8)	0.0610 (8)	−0.0001 (6)	−0.0028 (6)	−0.0010 (6)
O1W	0.0977 (9)	0.0590 (7)	0.0571 (7)	0.0094 (7)	−0.0037 (6)	0.0049 (6)

Geometric parameters (Å, º)

C1—C2	1.3499 (19)	C7—H7	0.9300
C1—N1	1.3661 (17)	C8—N3	1.3411 (19)
C1—H1	0.9300	C8—H8	0.9300
C2—N2	1.3720 (18)	C9—N1	1.4658 (15)
C2—H2	0.9300	C9—C10	1.5074 (18)
C3—N2	1.3295 (16)	C9—H9A	0.9700
C3—N1	1.3657 (16)	C9—H9B	0.9700
C3—C4	1.4664 (19)	C10—C11	1.3834 (17)
C4—N3	1.3373 (16)	C10—C12	1.3844 (19)
C4—C5	1.3844 (18)	C11—C12^i	1.3815 (18)
C5—C6	1.3690 (19)	C11—H11	0.9300
C5—H5	0.9300	C12—C11^i	1.3815 (18)
C6—C7	1.372 (2)	C12—H12	0.9300
C6—H6	0.9300	O1W—H1A	0.873 (9)
C7—C8	1.372 (2)	O1W—H1B	0.860 (9)
C2—C1—N1	106.35 (13)	C7—C8—H8	117.9
C2—C1—H1	126.8	N1—C9—C10	113.30 (10)
N1—C1—H1	126.8	N1—C9—H9A	108.9
C1—C2—N2	110.54 (13)	C10—C9—H9A	108.9
C1—C2—H2	124.7	N1—C9—H9B	108.9
N2—C2—H2	124.7	C10—C9—H9B	108.9
N2—C3—N1	110.61 (12)	H9A—C9—H9B	107.7
N2—C3—C4	122.95 (12)	C11—C10—C12	117.67 (12)
N1—C3—C4	126.42 (12)	C11—C10—C9	121.88 (12)
N3—C4—C5	122.37 (13)	C12—C10—C9	120.40 (12)
N3—C4—C3	117.75 (12)	C12^i—C11—C10	121.08 (13)
C5—C4—C3	119.88 (12)	C12^i—C11—H11	119.5
C6—C5—C4	119.33 (14)	C10—C11—H11	119.5
C6—C5—H5	120.3	C11^i—C12—C10	121.24 (13)
C4—C5—H5	120.3	C11^i—C12—H12	119.4
C5—C6—C7	119.26 (15)	C10—C12—H12	119.4
C5—C6—H6	120.4	C3—N1—C1	107.13 (12)
C7—C6—H6	120.4	C3—N1—C9	129.14 (11)
C6—C7—C8	117.97 (14)	C1—N1—C9	123.72 (12)
C6—C7—H7	121.0	C3—N2—C2	105.36 (12)
C8—C7—H7	121.0	C4—N3—C8	116.85 (13)
N3—C8—C7	124.23 (15)	H1A—O1W—H1B	105.9 (12)
N3—C8—H8	117.9
N1—C1—C2—N2	−0.12 (16)	C9—C10—C12—C11^i	−176.60 (12)
N2—C3—C4—N3	−167.83 (12)	N2—C3—N1—C1	−0.22 (14)
N1—C3—C4—N3	10.66 (19)	C4—C3—N1—C1	−178.86 (12)
N2—C3—C4—C5	11.21 (19)	N2—C3—N1—C9	−179.02 (11)
N1—C3—C4—C5	−170.30 (12)	C4—C3—N1—C9	2.3 (2)
N3—C4—C5—C6	0.0 (2)	C2—C1—N1—C3	0.20 (15)
C3—C4—C5—C6	−178.95 (12)	C2—C1—N1—C9	179.08 (11)
C4—C5—C6—C7	0.5 (2)	C10—C9—N1—C3	77.88 (17)
C5—C6—C7—C8	−0.7 (2)	C10—C9—N1—C1	−100.74 (15)
C6—C7—C8—N3	0.3 (2)	N1—C3—N2—C2	0.14 (14)
N1—C9—C10—C11	41.69 (17)	C4—C3—N2—C2	178.84 (12)
N1—C9—C10—C12	−140.92 (12)	C1—C2—N2—C3	−0.01 (16)
C12—C10—C11—C12^i	−0.9 (2)	C5—C4—N3—C8	−0.45 (19)
C9—C10—C11—C12^i	176.56 (12)	C3—C4—N3—C8	178.56 (12)
C11—C10—C12—C11^i	0.9 (2)	C7—C8—N3—C4	0.3 (2)

Symmetry code: (i) −x+1, −y, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1B···N2^ii	0.86 (1)	2.12 (1)	2.9636 (16)	169 (2)
O1W—H1A···O1W^iii	0.87 (1)	1.96 (1)	2.8258 (19)	176 (2)

Symmetry codes: (ii) x−1, −y+1/2, z+1/2; (iii) x, −y+1/2, z−1/2.