2-(2-Fur­yl)-1H-imidazo[4,5-f][1,10]phenanthroline-3,7-diium dichloride monohydrate

Chen, M.-H.; Zhang, Y.-Q.; Zhu, Q.-J.; Xue, S.-F.; Tao, Z.

doi:10.1107/S1600536809001160

organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o341

doi:10.1107/S1600536809001160

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2-(2-Furyl)-1H-imidazo[4,5-f][1,10]phenanthroline-3,7-diium dichloride monohydrate

Ming-Hua Chen,^a Yun-Qian Zhang,^a Qian-Jiang Zhu,^a ^* Sai-Feng Xue ^a and Zhu Tao ^a,^b

^aKey Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang 550025, People's Republic of China, and ^bInstitute of Applied Chemistry, Guizhou University, Guiyang 550025, People's Republic of China
^*Correspondence e-mail: sci.yqzhang@gzu.edu.cn

(Received 8 January 2009; accepted 10 January 2009; online 17 January 2009)

The organic cation of the title salt, C₁₇H₁₂N₄O²⁺·2Cl⁻·H₂O, is nearly planar, the dihedral angle between two pyridine rings being 2.53 (16)° and that between the pyridinum and furan rings being 4.17 (19)°. Molecules are linked via N—H⋯O, N—H⋯Cl and O—H⋯Cl hydrogen bonds, forming a three-dimensional framework and π–π stacking interactions help to stabilize the crystal structure [the imidazole–pyridine and imidazole–benzene centroid–centroid distances are 3.501 (3) and 3.674 (3) Å; respectively].

Related literature

For general background, see: Zhao et al. (2004 ); Zheng et al. (2005 ).

Experimental

Crystal data

C₁₇H₁₂N₄O²⁺·2Cl⁻·H₂O
M_r = 377.22
Monoclinic, P 2₁ /n
a = 4.768 (3) Å
b = 17.897 (10) Å
c = 19.241 (11) Å
β = 92.060 (8)°
V = 1641.0 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.42 mm⁻¹
T = 293 (2) K
0.23 × 0.18 × 0.15 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.911, T_max = 0.940
10782 measured reflections
2859 independent reflections
1886 reflections with I > 2σ(I)
R_int = 0.058

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.115
S = 1.02
2859 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1W	0.86	1.76	2.618 (3)	177
N2—H2A⋯Cl1	0.86	2.12	2.981 (3)	179
N4—H4⋯Cl2ⁱ	0.86	2.33	3.103 (3)	150
O1W—H1WA⋯Cl2ⁱⁱ	1.02	2.00	3.011 (3)	172
O1W—H1WB⋯Cl2ⁱⁱⁱ	0.93	2.19	3.112 (3)	173
Symmetry codes: (i) x+1, y, z; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809001160/at2707sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809001160/at2707Isup2.hkl

checkCIF report

Comment top

Recent year, we used different alkyl-substituted glycolurils as the building blocks to synthesize the partially alkyl substituted cucurbit[n]urils (Zhao et al., 2004; Zheng et al., 2005). In this work, we further report the crystal structure of a phenanthroline-substituted semi-glycoluril.

The molecular structure of the title compound (I), consists of organic cations, two Cl^- anions and one water molecule (Fig. 1). The organic cation is nearly planar, the dihedral angle between two pyridine rings is 2.53 (16) ° and that one between N4-pyridine ring and furan ring is 4.17 (19)°. Molecules are linked via N1—H1A···O1W, N2—H2A···Cl1, N4—H4···Cl2, O1W—H1WA···Cl2 and O1W—H1WB···Cl2 hydrogen bonds (Table 1) forming a three-dimensional framework. In additional, the π···π stacking interaction occurs between adjacent organic cations, the centroid-to-centroid distance of Cg2 to Cg3^iv is 3.501 (3)Å and Cg2 to Cg5^iv is 3.674 (3)Å [Cg2, Cg3 and Cg5 is the centroid of the N1-imidazole ring, N3-pyridine ring and C6-benzene ring, respectively. Symmerty codes: (iv) -1 + x, y, z].

Related literature top

For general background, see: Zhao et al. (2004); Zheng et al. (2005).

Experimental top

1,10-Phenanthroline-5,6-dione (1.0 g, 4.75 mmol) and ammonium acetate (3.9 g, 5 mmol) are dissolved in acetic acid glacial (60 mL) at 333 K, after cooling at room temperature, we can get lots of yellow deposits by the neutrlizing with ammonia to pH = 8–9 after 4 h of mixing with furaldhyde (0.8 mL) at 353 K. After the recryslalization in ethanol, the yellow product was dissolved in the dilute hydrochloric acid and red-brown crystals were obtained

after ten days.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. The molecular structure of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.

2-(2-Furyl)-1H-imidazo[4,5-f][1,10]phenanthroline- 3,7-diium dichloride monohydrate top

Crystal data top

C₁₇H₁₂N₄O²⁺·2Cl⁻·H₂O	F(000) = 776
M_r = 377.22	D_x = 1.527 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2859 reflections
a = 4.768 (3) Å	θ = 1.6–25.0°
b = 17.897 (10) Å	µ = 0.42 mm⁻¹
c = 19.241 (11) Å	T = 293 K
β = 92.060 (8)°	Prism, red-brown
V = 1641.0 (16) Å³	0.23 × 0.18 × 0.15 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	2859 independent reflections
Radiation source: fine-focus sealed tube	1886 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.058
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −5→5
T_min = 0.911, T_max = 0.940	k = −20→21
10782 measured reflections	l = −22→22

Refinement top

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.115	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0514P)²] where P = (F_o² + 2F_c²)/3
2859 reflections	(Δ/σ)_max < 0.001
226 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₇H₁₂N₄O²⁺·2Cl⁻·H₂O	V = 1641.0 (16) Å³
M_r = 377.22	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 4.768 (3) Å	µ = 0.42 mm⁻¹
b = 17.897 (10) Å	T = 293 K
c = 19.241 (11) Å	0.23 × 0.18 × 0.15 mm
β = 92.060 (8)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	2859 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1886 reflections with I > 2σ(I)
T_min = 0.911, T_max = 0.940	R_int = 0.058
10782 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.115	H-atom parameters constrained
S = 1.02	Δρ_max = 0.19 e Å⁻³
2859 reflections	Δρ_min = −0.26 e Å⁻³
226 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.2549 (7)	0.5257 (2)	0.91899 (18)	0.0595 (10)
H1	0.1981	0.5270	0.9647	0.071*
C2	0.1543 (7)	0.57043 (18)	0.86872 (17)	0.0491 (9)
H2	0.0184	0.6073	0.8728	0.059*
C3	0.2960 (6)	0.55060 (16)	0.80743 (16)	0.0439 (8)
H3	0.2711	0.5718	0.7635	0.053*
C4	0.4742 (6)	0.49469 (16)	0.82609 (15)	0.0366 (7)
C5	0.6721 (6)	0.45050 (15)	0.78964 (15)	0.0356 (7)
C6	0.9978 (6)	0.36694 (15)	0.76729 (14)	0.0334 (7)
C7	1.2049 (6)	0.30919 (15)	0.77145 (14)	0.0331 (7)
C8	1.2878 (6)	0.26901 (16)	0.83160 (16)	0.0405 (8)
H8	1.2062	0.2786	0.8739	0.049*
C9	1.4924 (6)	0.21529 (17)	0.82645 (16)	0.0465 (8)
H9	1.5506	0.1877	0.8653	0.056*
C10	1.6108 (6)	0.20276 (16)	0.76279 (17)	0.0453 (8)
H10	1.7500	0.1665	0.7607	0.054*
C11	1.3351 (6)	0.29168 (15)	0.70909 (14)	0.0328 (7)
C12	1.2531 (6)	0.33026 (15)	0.64536 (14)	0.0320 (7)
C13	1.3161 (6)	0.34323 (16)	0.52471 (15)	0.0417 (8)
H13	1.4109	0.3287	0.4855	0.050*
C14	1.1068 (6)	0.39700 (16)	0.51891 (15)	0.0420 (8)
H14	1.0577	0.4177	0.4758	0.050*
C15	0.9734 (6)	0.41932 (15)	0.57711 (14)	0.0376 (7)
H15	0.8349	0.4559	0.5741	0.045*
C16	1.0477 (6)	0.38639 (15)	0.64198 (14)	0.0322 (7)
C17	0.9259 (6)	0.40383 (15)	0.70643 (14)	0.0319 (7)
N3	1.5391 (5)	0.23910 (13)	0.70414 (13)	0.0412 (6)
N4	1.3821 (5)	0.31224 (12)	0.58612 (12)	0.0359 (6)
H4	1.5130	0.2792	0.5882	0.043*
N1	0.8358 (5)	0.39716 (13)	0.81854 (11)	0.0348 (6)
H1A	0.8394	0.3840	0.8615	0.042*
N2	0.7228 (5)	0.45605 (12)	0.72179 (12)	0.0345 (6)
H2A	0.6432	0.4867	0.6928	0.041*
O1	0.4528 (5)	0.47741 (12)	0.89489 (11)	0.0550 (6)
Cl1	0.44997 (17)	0.56432 (4)	0.62293 (4)	0.0514 (3)
Cl2	0.83425 (17)	0.20341 (5)	0.53339 (5)	0.0579 (3)
O1W	0.8356 (5)	0.35229 (14)	0.94806 (11)	0.0703 (8)
H1WA	0.9993	0.3370	0.9803	0.084*
H1WB	0.6840	0.3400	0.9751	0.084*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.053 (2)	0.077 (3)	0.049 (2)	0.008 (2)	0.0175 (18)	−0.016 (2)
C2	0.047 (2)	0.046 (2)	0.055 (2)	0.0040 (16)	0.0111 (17)	−0.0081 (17)
C3	0.048 (2)	0.0404 (19)	0.044 (2)	0.0041 (16)	0.0072 (16)	0.0008 (15)
C4	0.0363 (17)	0.0435 (18)	0.0304 (17)	−0.0035 (15)	0.0052 (14)	−0.0034 (14)
C5	0.0371 (18)	0.0338 (17)	0.0360 (19)	−0.0036 (14)	0.0023 (14)	−0.0014 (13)
C6	0.0325 (16)	0.0372 (17)	0.0307 (17)	−0.0030 (14)	0.0030 (13)	−0.0017 (13)
C7	0.0321 (16)	0.0339 (17)	0.0331 (18)	−0.0038 (13)	0.0004 (13)	0.0010 (13)
C8	0.0395 (18)	0.0436 (19)	0.0387 (18)	0.0014 (15)	0.0033 (14)	0.0035 (15)
C9	0.051 (2)	0.046 (2)	0.042 (2)	0.0001 (16)	−0.0055 (16)	0.0126 (15)
C10	0.0442 (19)	0.0371 (19)	0.054 (2)	0.0061 (15)	−0.0062 (17)	−0.0002 (16)
C11	0.0309 (16)	0.0328 (17)	0.0344 (18)	−0.0052 (13)	−0.0028 (13)	−0.0023 (13)
C12	0.0302 (16)	0.0345 (17)	0.0314 (17)	−0.0060 (13)	0.0043 (13)	−0.0048 (13)
C13	0.049 (2)	0.0446 (19)	0.0318 (18)	−0.0005 (16)	0.0065 (15)	−0.0037 (14)
C14	0.053 (2)	0.0402 (19)	0.0327 (18)	−0.0001 (16)	0.0047 (15)	0.0011 (14)
C15	0.0422 (18)	0.0368 (18)	0.0339 (18)	0.0011 (14)	0.0025 (14)	0.0043 (14)
C16	0.0331 (16)	0.0308 (16)	0.0329 (17)	−0.0045 (13)	0.0019 (13)	−0.0018 (13)
C17	0.0332 (16)	0.0310 (16)	0.0314 (17)	−0.0010 (13)	0.0010 (13)	−0.0022 (13)
N3	0.0389 (15)	0.0349 (15)	0.0497 (17)	0.0050 (12)	−0.0006 (12)	−0.0030 (12)
N4	0.0351 (14)	0.0377 (15)	0.0349 (15)	0.0019 (11)	0.0009 (11)	−0.0045 (11)
N1	0.0371 (14)	0.0396 (15)	0.0281 (14)	−0.0006 (12)	0.0062 (11)	0.0040 (11)
N2	0.0364 (14)	0.0356 (14)	0.0315 (15)	0.0042 (11)	0.0023 (11)	0.0033 (11)
O1	0.0560 (15)	0.0699 (16)	0.0400 (14)	0.0159 (12)	0.0122 (11)	0.0021 (11)
Cl1	0.0573 (5)	0.0518 (5)	0.0452 (5)	0.0106 (4)	0.0014 (4)	0.0082 (4)
Cl2	0.0407 (5)	0.0682 (6)	0.0651 (6)	0.0031 (4)	0.0057 (4)	−0.0194 (5)
O1W	0.0487 (15)	0.120 (2)	0.0432 (14)	0.0106 (14)	0.0133 (11)	0.0309 (14)

Geometric parameters (Å, º) top

C1—C2	1.332 (4)	C10—N3	1.336 (4)
C1—O1	1.373 (4)	C10—H10	0.9300
C1—H1	0.9300	C11—N3	1.359 (3)
C2—C3	1.425 (4)	C11—C12	1.449 (4)
C2—H2	0.9300	C12—N4	1.353 (3)
C3—C4	1.353 (4)	C12—C16	1.403 (4)
C3—H3	0.9300	C13—N4	1.333 (3)
C4—O1	1.367 (3)	C13—C14	1.388 (4)
C4—C5	1.434 (4)	C13—H13	0.9300
C5—N2	1.340 (3)	C14—C15	1.367 (4)
C5—N1	1.341 (3)	C14—H14	0.9300
C6—C17	1.377 (4)	C15—C16	1.414 (4)
C6—N1	1.384 (3)	C15—H15	0.9300
C6—C7	1.429 (4)	C16—C17	1.423 (4)
C7—C11	1.406 (4)	C17—N2	1.385 (3)
C7—C8	1.407 (4)	N4—H4	0.8600
C8—C9	1.376 (4)	N1—H1A	0.8600
C8—H8	0.9300	N2—H2A	0.8600
C9—C10	1.385 (4)	O1W—H1WA	1.0173
C9—H9	0.9300	O1W—H1WB	0.9323

C2—C1—O1	111.5 (3)	C7—C11—C12	120.1 (3)
C2—C1—H1	124.2	N4—C12—C16	118.0 (3)
O1—C1—H1	124.2	N4—C12—C11	118.8 (3)
C1—C2—C3	106.4 (3)	C16—C12—C11	123.2 (3)
C1—C2—H2	126.8	N4—C13—C14	120.4 (3)
C3—C2—H2	126.8	N4—C13—H13	119.8
C4—C3—C2	106.1 (3)	C14—C13—H13	119.8
C4—C3—H3	127.0	C15—C14—C13	119.4 (3)
C2—C3—H3	127.0	C15—C14—H14	120.3
C3—C4—O1	110.9 (3)	C13—C14—H14	120.3
C3—C4—C5	134.1 (3)	C14—C15—C16	119.5 (3)
O1—C4—C5	115.0 (3)	C14—C15—H15	120.3
N2—C5—N1	109.5 (3)	C16—C15—H15	120.3
N2—C5—C4	125.5 (3)	C12—C16—C15	119.5 (3)
N1—C5—C4	125.0 (3)	C12—C16—C17	115.0 (2)
C17—C6—N1	106.9 (2)	C15—C16—C17	125.5 (3)
C17—C6—C7	123.0 (3)	C6—C17—N2	107.3 (2)
N1—C6—C7	130.1 (3)	C6—C17—C16	122.6 (3)
C11—C7—C8	117.9 (3)	N2—C17—C16	130.1 (2)
C11—C7—C6	116.0 (2)	C10—N3—C11	116.1 (3)
C8—C7—C6	126.1 (3)	C13—N4—C12	123.2 (3)
C9—C8—C7	118.5 (3)	C13—N4—H4	118.4
C9—C8—H8	120.8	C12—N4—H4	118.4
C7—C8—H8	120.8	C5—N1—C6	108.3 (2)
C8—C9—C10	119.3 (3)	C5—N1—H1A	125.8
C8—C9—H9	120.3	C6—N1—H1A	125.8
C10—C9—H9	120.3	C5—N2—C17	108.1 (2)
N3—C10—C9	124.6 (3)	C5—N2—H2A	126.0
N3—C10—H10	117.7	C17—N2—H2A	126.0
C9—C10—H10	117.7	C4—O1—C1	105.1 (2)
N3—C11—C7	123.6 (3)	H1WA—O1W—H1WB	100.9
N3—C11—C12	116.3 (3)

O1—C1—C2—C3	−0.3 (4)	C11—C12—C16—C17	0.8 (4)
C1—C2—C3—C4	−0.2 (4)	C14—C15—C16—C12	−1.3 (4)
C2—C3—C4—O1	0.5 (3)	C14—C15—C16—C17	−179.7 (3)
C2—C3—C4—C5	179.6 (3)	N1—C6—C17—N2	0.3 (3)
C3—C4—C5—N2	−0.9 (5)	C7—C6—C17—N2	−179.4 (2)
O1—C4—C5—N2	178.1 (3)	N1—C6—C17—C16	−178.8 (2)
C3—C4—C5—N1	178.9 (3)	C7—C6—C17—C16	1.4 (4)
O1—C4—C5—N1	−2.0 (4)	C12—C16—C17—C6	−1.9 (4)
C17—C6—C7—C11	0.2 (4)	C15—C16—C17—C6	176.6 (3)
N1—C6—C7—C11	−179.5 (3)	C12—C16—C17—N2	179.2 (3)
C17—C6—C7—C8	−179.7 (3)	C15—C16—C17—N2	−2.3 (5)
N1—C6—C7—C8	0.6 (5)	C9—C10—N3—C11	0.0 (4)
C11—C7—C8—C9	0.4 (4)	C7—C11—N3—C10	0.9 (4)
C6—C7—C8—C9	−179.6 (3)	C12—C11—N3—C10	−178.9 (2)
C7—C8—C9—C10	0.4 (4)	C14—C13—N4—C12	0.2 (4)
C8—C9—C10—N3	−0.6 (5)	C16—C12—N4—C13	−2.5 (4)
C8—C7—C11—N3	−1.1 (4)	C11—C12—N4—C13	178.2 (2)
C6—C7—C11—N3	179.0 (2)	N2—C5—N1—C6	−0.2 (3)
C8—C7—C11—C12	178.7 (2)	C4—C5—N1—C6	179.9 (3)
C6—C7—C11—C12	−1.3 (4)	C17—C6—N1—C5	−0.1 (3)
N3—C11—C12—N4	−0.2 (4)	C7—C6—N1—C5	179.6 (3)
C7—C11—C12—N4	180.0 (2)	N1—C5—N2—C17	0.4 (3)
N3—C11—C12—C16	−179.4 (2)	C4—C5—N2—C17	−179.7 (3)
C7—C11—C12—C16	0.8 (4)	C6—C17—N2—C5	−0.4 (3)
N4—C13—C14—C15	1.6 (4)	C16—C17—N2—C5	178.6 (3)
C13—C14—C15—C16	−1.0 (4)	C3—C4—O1—C1	−0.7 (3)
N4—C12—C16—C15	3.0 (4)	C5—C4—O1—C1	−180.0 (3)
C11—C12—C16—C15	−177.8 (2)	C2—C1—O1—C4	0.6 (4)
N4—C12—C16—C17	−178.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1W	0.86	1.76	2.618 (3)	177
N2—H2A···Cl1	0.86	2.12	2.981 (3)	179
N4—H4···Cl2ⁱ	0.86	2.33	3.103 (3)	150
O1W—H1WA···Cl2ⁱⁱ	1.02	2.00	3.011 (3)	172
O1W—H1WB···Cl2ⁱⁱⁱ	0.93	2.19	3.112 (3)	173

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₂N₄O²⁺·2Cl⁻·H₂O
M_r	377.22
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	4.768 (3), 17.897 (10), 19.241 (11)
β (°)	92.060 (8)
V (Å³)	1641.0 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.42
Crystal size (mm)	0.23 × 0.18 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.911, 0.940
No. of measured, independent and observed [I > 2σ(I)] reflections	10782, 2859, 1886
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.115, 1.02
No. of reflections	2859
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.26

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1W	0.86	1.76	2.618 (3)	176.6
N2—H2A···Cl1	0.86	2.12	2.981 (3)	178.7
N4—H4···Cl2ⁱ	0.86	2.33	3.103 (3)	150.3
O1W—H1WA···Cl2ⁱⁱ	1.02	2.00	3.011 (3)	172.0
O1W—H1WB···Cl2ⁱⁱⁱ	0.93	2.19	3.112 (3)	172.7

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

Acknowledgements

We acknowledge the support of the National Natural Science Foundation of China (No. 20662003), the International Collaborative Project of the Ministry of Science and Technology (No. 2007400108) and the Foundation of the Governor of Guizhou Province, China.

References

Bruker, (2005). APPEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhao, Y. J., Xue, S. F., Zhu, Q. J., Tao, Z., Zhang, J. X., Wei, Z. B., Long, L. S., Hu, M. L., Xiao, H. P. & Day, A. I. (2004). Chin. Sci. Bull. 49, 1111–1116. Web of Science CSD CrossRef CAS Google Scholar
Zheng, L. M., Zhu, J. N., Zhang, Y. Q., Tao, Z., Xue, S. F., Zhu, Q. J., Wei, Z. B. & Long, L. S. (2005). Chin. J. Inorg. Chem. 21, 1583–1588. CAS Google Scholar

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Volume 65| Part 2| February 2009| Page o341

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2-(2-Fur­yl)-1H-imidazo[4,5-f][1,10]phenanthroline-3,7-diium dichloride monohydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-(2-Furyl)-1H-imidazo[4,5-f][1,10]phenanthroline-3,7-diium dichloride monohydrate