1-[4-(3-{[5-(4-Chloro­phen­yl)furan-2-yl]methyl­idene­amino}-2,5-dioxoimidazol­idin-1-yl)but­yl]-4-methyl­piperazine-1,4-diium dichloride hemihydrate

Liang, Y.-S.; Mu, S.; Liu, Y.; Liu, D.-K.

doi:10.1107/S1600536811000560

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o320

doi:10.1107/S1600536811000560

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1-[4-(3-{[5-(4-Chlorophenyl)furan-2-yl]methylideneamino}-2,5-dioxoimidazolidin-1-yl)butyl]-4-methylpiperazine-1,4-diium dichloride hemihydrate

Yan-Shu Liang,^a Shuai Mu,^b ^* Ying Liu ^c and Deng-Ke Liu ^c

^aTianjin University of Commerce, Tianjin 300134, People's Republic of China, ^bSchool of Chemical Engineering and Technology, Tianjin University, Tianjin, 300072, People's Republic of China, and ^cTianjin Institute of Pharmaceutical Research, Tianjin, 300193, People's Republic of China
^*Correspondence e-mail: myth4307@tju.edu.cn

(Received 9 December 2010; accepted 5 January 2011; online 12 January 2011)

The title compound, C₂₃H₃₀ClN₅O₃²⁺·2Cl⁻·0.5H₂O, was synthesized by N-alkylation of 1-({[5-(4-chlorophenyl)-2-furanyl]methylene}amino)-2,4-imidazolidinedione with 1-bromo-4-chlorobutane, and N-methylpiperazine. In the crystal, the cations, anions and water molecules are linked by O—H⋯Cl and N—H⋯Cl hydrogen bonds.

Related literature

For bond-length data, see: Allen et al. (1987 ). For background to the bioactivity and applications of the title compound, see: Pratt et al. (2004 ). For the preparation of the title compound, see: Matson et al. (1999 ).

Experimental

Crystal data

C₂₃H₃₀ClN₅O₃²⁺·2Cl⁻·0.5H₂O
M_r = 539.88
Monoclinic, C 2/c
a = 59.563 (12) Å
b = 6.8793 (14) Å
c = 12.831 (2) Å
β = 94.402 (4)°
V = 5241.9 (18) Å³
Z = 8
Mo Kα radiation
μ = 0.39 mm⁻¹
T = 294 K
0.20 × 0.14 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.725, T_max = 1.000
12667 measured reflections
4629 independent reflections
2498 reflections with I > 2σ(I)
R_int = 0.059

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.123
S = 1.00
4629 reflections
321 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4B⋯Cl3	0.86	2.40	3.250 (3)	169
O4—H4C⋯Cl3ⁱ	0.85	2.50	3.250 (3)	148
N5—H5A⋯Cl2ⁱⁱ	1.05 (4)	1.95 (4)	2.995 (3)	174 (3)
N4—H4A⋯Cl3	1.04 (4)	2.00 (4)	3.035 (3)	178 (3)
Symmetry codes: (i) $[-x, y, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y+2, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811000560/kp2297sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811000560/kp2297Isup2.hkl

checkCIF report

Comment top

The compound, 1-[[[5-(4-chlorophenyl)-2-furanyl]methylene]amino]-3- [4-(4-methyl-1-piperazinyl)butyl]-2, 4-imidazolidinedione dihydrochloride (Azimilide dihydrochloride), (I), is a Vaughan-Williamsclass III antiarrhythmic drug, which is being developed primarily for atrial fibrillation and also as adjunctive antiarrhythmic therapy in patients with implantable cardioverter defibrillators (Pratt et al., 2004). Now, we present the crystal structure of the title compound (Fig. 1).

All bond lengths and angles in (I) are within normal ranges (Allen et al., 1987) except for the N—H bonds involved in hydrogen bonds with charged donors N4—H4A (1.04 Å) and N5—H5A (1.05 Å)of piperazonia ring, and also chloride ions Cl₂^- and Cl₃^- as the acceptors. In the crystal, the imidazolidine-2,4-dione ring (C12/C13/C14/N2/N3/O2/O3) is planar with the r.m.s. deviation of 0.0029 Å. The dihedral angle formed between the imidazolidine-2,4-dione ring plane (A), the benzene ring plane (C1 to C6, B) and the furan ring plane (C7/C8/C9/C10/O1, C) are 28.67 (15) ° (A/B), 12.06 (3) ° (B/C) and 18.73 (18) ° (A/C), respectively. The piperazonia ring adopts a chair conformation. The packing is stabilized by intermolecular O—H···Cl and N—H···Cl hydrogen bonds (Table 1 and Fig. 2).

Related literature top

For bond-length data, see: Allen et al. (1987). For background to the bioactivity and applications of the title compound, see: Pratt et al. (2004). For the preparation of the title compound, see: Matson et al. (1999).

Experimental top

The title compound was prepared according to the method of Matson et al. (1999). A three-neck 1 L flask fitted with a thermometer, mechanical stirrer, heating mantle, reflux condenser and addition funnel is charged with DMF (240 ml) and heated to 323 K. 1-[[[5-(4-Chlorophenyl)-2-furanyl]methylene]amino]-2,4- imidazolidinedione (29 g) is added and heating is continued. When dissolution is completed, potassium carbonate (14 g) is charged to the flask and heating is continued to 353 K. After 20 minutes, 1-bromo-4-chlorobutane (18.5 g) is added, and heating is continued to approximately 373 K. After 50 minutes, N-methylpiperazine (23.5 g) is added, and the mixture is allowed to stir for 2 h at 373 K. The reaction mixture is cooled to approximately 283 K and filtered to remove insolubles. The DMF is removed under reduced pressure at 338–341 K and replaced with absolute ethanol (175 ml). The mixture is heated to dissolve the free base and filtered to remove insolubles. The product is precipitated from ethanol (300 ml total) with the addition of 20 g of concentrated hydrochloric acid and then filtered to give 31 g of Azimilide dihydrochloride. The above dihydrochloride is suspended in 670 ml of refluxing ethanol and 150 ml of water are added to obtain complete solubilization. The mixture was standing under 298 K, then white crystals were grown slowly. The crystals were washed with cold ethanol, yield 25.6 g.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I) with the atom-numbering scheme and 30% probability displacement ellipsoids.
	Fig. 2. Packing diagram for (I) with hydrogen bonds drawn by dashed lines.

1-[4-(3-{[5-(4-Chlorophenyl)furan-2-yl]methylideneamino}-2,5- dioxoimidazolidin-1-yl)butyl]-4-methylpiperazine-1,4-diium dichloride hemihydrate top

Crystal data top

C₂₃H₃₀ClN₅O₃²⁺·2Cl⁻·0.5H₂O	F(000) = 2264
M_r = 539.88	D_x = 1.368 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2226 reflections
a = 59.563 (12) Å	θ = 2.7–27.7°
b = 6.8793 (14) Å	µ = 0.39 mm⁻¹
c = 12.831 (2) Å	T = 294 K
β = 94.402 (4)°	Prism, white
V = 5241.9 (18) Å³	0.20 × 0.14 × 0.08 mm
Z = 8

Data collection top

Bruker SMART CCD area-detector diffractometer	4629 independent reflections
Radiation source: fine-focus sealed tube	2498 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.059
ϕ and ω scans	θ_max = 25.0°, θ_min = 0.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −70→70
T_min = 0.725, T_max = 1.000	k = −3→8
12667 measured reflections	l = −14→15

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0367P)² + 5.8309P] where P = (F_o² + 2F_c²)/3
4629 reflections	(Δ/σ)_max = 0.002
321 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₂₃H₃₀ClN₅O₃²⁺·2Cl⁻·0.5H₂O	V = 5241.9 (18) Å³
M_r = 539.88	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 59.563 (12) Å	µ = 0.39 mm⁻¹
b = 6.8793 (14) Å	T = 294 K
c = 12.831 (2) Å	0.20 × 0.14 × 0.08 mm
β = 94.402 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4629 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2498 reflections with I > 2σ(I)
T_min = 0.725, T_max = 1.000	R_int = 0.059
12667 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.34 e Å⁻³
4629 reflections	Δρ_min = −0.28 e Å⁻³
321 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	Occ. (<1)
Cl1	0.23396 (2)	0.4537 (2)	−0.45468 (9)	0.0911 (5)
O1	0.18447 (4)	0.8711 (4)	−0.05974 (19)	0.0462 (7)
O2	0.14878 (5)	0.4220 (4)	0.1843 (2)	0.0589 (8)
O3	0.12471 (4)	0.8338 (4)	0.43121 (19)	0.0515 (7)
N1	0.15913 (5)	0.7902 (5)	0.1069 (2)	0.0440 (8)
N2	0.14652 (5)	0.7590 (5)	0.1904 (2)	0.0448 (8)
N3	0.13558 (5)	0.5894 (4)	0.3246 (2)	0.0400 (8)
N4	0.06729 (5)	0.5843 (4)	0.5197 (2)	0.0337 (7)
N5	0.04067 (5)	0.8887 (5)	0.6061 (2)	0.0390 (8)
C1	0.22367 (7)	0.9011 (7)	−0.2680 (3)	0.0650 (13)
H1	0.2290	1.0276	−0.2592	0.078*
C2	0.23197 (7)	0.7838 (9)	−0.3432 (3)	0.0690 (14)
H2	0.2430	0.8308	−0.3840	0.083*
C3	0.22404 (7)	0.5989 (8)	−0.3580 (3)	0.0594 (12)
C4	0.20785 (7)	0.5277 (7)	−0.2977 (3)	0.0630 (13)
H4	0.2023	0.4022	−0.3083	0.076*
C5	0.19981 (7)	0.6438 (7)	−0.2213 (3)	0.0573 (12)
H5	0.1890	0.5946	−0.1797	0.069*
C6	0.20750 (6)	0.8320 (7)	−0.2054 (3)	0.0485 (11)
C7	0.19819 (7)	0.9568 (6)	−0.1273 (3)	0.0478 (11)
C8	0.19909 (7)	1.1508 (7)	−0.1081 (3)	0.0600 (12)
H8	0.2073	1.2418	−0.1429	0.072*
C9	0.18542 (7)	1.1891 (7)	−0.0263 (3)	0.0574 (12)
H9	0.1827	1.3098	0.0030	0.069*
C10	0.17690 (7)	1.0172 (6)	0.0018 (3)	0.0452 (10)
C11	0.16305 (6)	0.9676 (6)	0.0845 (3)	0.0444 (10)
H11	0.1568	1.0662	0.1225	0.053*
C12	0.14429 (6)	0.5725 (6)	0.2266 (3)	0.0439 (10)
C13	0.13208 (6)	0.7804 (6)	0.3510 (3)	0.0394 (9)
C14	0.13935 (6)	0.9033 (5)	0.2631 (3)	0.0422 (10)
H14A	0.1270	0.9805	0.2321	0.051*
H14B	0.1517	0.9888	0.2867	0.051*
C15	0.13341 (6)	0.4226 (6)	0.3940 (3)	0.0461 (10)
H15A	0.1346	0.4677	0.4658	0.055*
H15B	0.1458	0.3340	0.3857	0.055*
C16	0.11156 (6)	0.3135 (6)	0.3737 (3)	0.0464 (10)
H16A	0.1118	0.2014	0.4197	0.056*
H16B	0.1106	0.2658	0.3024	0.056*
C17	0.09061 (6)	0.4316 (6)	0.3897 (3)	0.0424 (10)
H17A	0.0774	0.3566	0.3660	0.051*
H17B	0.0907	0.5486	0.3475	0.051*
C18	0.08908 (6)	0.4875 (6)	0.5033 (3)	0.0413 (10)
H18A	0.0906	0.3719	0.5464	0.050*
H18B	0.1014	0.5747	0.5248	0.050*
C19	0.06381 (6)	0.5970 (6)	0.6343 (2)	0.0426 (10)
H19A	0.0643	0.4676	0.6644	0.051*
H19B	0.0758	0.6730	0.6695	0.051*
C20	0.04159 (6)	0.6894 (6)	0.6511 (3)	0.0448 (10)
H20A	0.0295	0.6113	0.6179	0.054*
H20B	0.0396	0.6956	0.7253	0.054*
C21	0.04333 (7)	0.8767 (6)	0.4918 (3)	0.0463 (10)
H21A	0.0426	1.0061	0.4617	0.056*
H21B	0.0312	0.8002	0.4581	0.056*
C22	0.06551 (6)	0.7845 (5)	0.4732 (3)	0.0413 (10)
H22A	0.0776	0.8647	0.5041	0.050*
H22B	0.0671	0.7767	0.3987	0.050*
C23	0.01982 (7)	0.9928 (7)	0.6300 (3)	0.0593 (12)
H23A	0.0195	1.1188	0.5977	0.089*
H23B	0.0195	1.0073	0.7043	0.089*
H23C	0.0069	0.9196	0.6034	0.089*
Cl2	0.080376 (16)	0.89703 (15)	0.20687 (7)	0.0483 (3)
Cl3	0.027191 (17)	0.36360 (15)	0.41881 (7)	0.0530 (3)
H4A	0.0538 (6)	0.507 (5)	0.485 (3)	0.055 (12)*
H5A	0.0542 (7)	0.972 (6)	0.638 (3)	0.069 (13)*
O4	0.0000	0.6464 (6)	0.2500	0.0960 (16)
H4C	−0.0016	0.5712	0.1973	0.115*	0.50
H4B	0.0068	0.5826	0.3011	0.115*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0934 (10)	0.1185 (12)	0.0647 (8)	0.0178 (9)	0.0280 (7)	−0.0075 (8)
O1	0.0471 (16)	0.0461 (17)	0.0460 (15)	−0.0059 (14)	0.0077 (13)	0.0043 (14)
O2	0.081 (2)	0.0401 (17)	0.0583 (18)	0.0067 (16)	0.0215 (15)	−0.0113 (15)
O3	0.0632 (18)	0.0497 (18)	0.0428 (15)	0.0052 (15)	0.0115 (14)	−0.0118 (14)
N1	0.049 (2)	0.043 (2)	0.0403 (18)	−0.0018 (18)	0.0086 (16)	−0.0052 (17)
N2	0.059 (2)	0.0347 (19)	0.0426 (18)	0.0017 (18)	0.0164 (16)	−0.0054 (17)
N3	0.0466 (19)	0.0356 (19)	0.0383 (17)	0.0059 (16)	0.0072 (15)	−0.0029 (16)
N4	0.044 (2)	0.0320 (18)	0.0260 (15)	0.0009 (17)	0.0065 (14)	0.0021 (14)
N5	0.0400 (19)	0.037 (2)	0.0403 (18)	−0.0005 (17)	0.0081 (15)	−0.0068 (16)
C1	0.057 (3)	0.077 (4)	0.062 (3)	−0.017 (3)	0.011 (2)	0.005 (3)
C2	0.055 (3)	0.099 (4)	0.055 (3)	−0.012 (3)	0.021 (2)	0.003 (3)
C3	0.053 (3)	0.078 (4)	0.048 (3)	0.011 (3)	0.009 (2)	0.003 (3)
C4	0.069 (3)	0.065 (3)	0.056 (3)	0.001 (3)	0.014 (2)	0.010 (3)
C5	0.057 (3)	0.066 (3)	0.051 (3)	−0.003 (3)	0.017 (2)	0.007 (2)
C6	0.038 (2)	0.063 (3)	0.044 (2)	0.000 (2)	0.0021 (19)	0.011 (2)
C7	0.045 (3)	0.055 (3)	0.043 (2)	−0.007 (2)	0.002 (2)	0.012 (2)
C8	0.063 (3)	0.055 (3)	0.062 (3)	−0.016 (3)	0.004 (2)	0.015 (3)
C9	0.063 (3)	0.049 (3)	0.060 (3)	−0.011 (2)	0.000 (2)	0.000 (2)
C10	0.045 (3)	0.047 (3)	0.043 (2)	0.004 (2)	−0.0029 (19)	−0.003 (2)
C11	0.045 (2)	0.046 (3)	0.041 (2)	0.000 (2)	0.0013 (19)	−0.003 (2)
C12	0.042 (2)	0.044 (3)	0.046 (2)	0.003 (2)	0.0045 (19)	−0.002 (2)
C13	0.037 (2)	0.039 (2)	0.043 (2)	0.005 (2)	0.0008 (18)	−0.004 (2)
C14	0.046 (2)	0.037 (2)	0.044 (2)	0.000 (2)	0.0066 (18)	−0.008 (2)
C15	0.048 (3)	0.048 (3)	0.043 (2)	0.018 (2)	0.0067 (19)	0.008 (2)
C16	0.055 (3)	0.037 (2)	0.049 (2)	0.007 (2)	0.013 (2)	−0.002 (2)
C17	0.047 (2)	0.042 (2)	0.039 (2)	0.001 (2)	0.0049 (18)	−0.0055 (19)
C18	0.043 (2)	0.046 (2)	0.036 (2)	0.007 (2)	0.0035 (18)	0.0026 (19)
C19	0.061 (3)	0.043 (2)	0.0250 (18)	0.003 (2)	0.0079 (17)	0.0050 (18)
C20	0.056 (3)	0.045 (3)	0.035 (2)	−0.007 (2)	0.0135 (19)	−0.001 (2)
C21	0.060 (3)	0.042 (3)	0.037 (2)	0.007 (2)	0.0073 (19)	−0.001 (2)
C22	0.058 (3)	0.033 (2)	0.034 (2)	0.002 (2)	0.0128 (18)	0.0069 (18)
C23	0.049 (3)	0.066 (3)	0.064 (3)	0.008 (2)	0.017 (2)	−0.016 (3)
Cl2	0.0508 (6)	0.0441 (6)	0.0489 (6)	0.0031 (5)	−0.0043 (5)	0.0066 (5)
Cl3	0.0545 (7)	0.0547 (7)	0.0496 (6)	−0.0077 (6)	0.0021 (5)	−0.0077 (5)
O4	0.156 (5)	0.046 (3)	0.086 (3)	0.000	0.014 (3)	0.000

Geometric parameters (Å, º) top

Cl1—C3	1.732 (4)	C9—C10	1.347 (5)
O1—C7	1.370 (4)	C9—H9	0.9300
O1—C10	1.375 (4)	C10—C11	1.434 (5)
O2—C12	1.208 (4)	C11—H11	0.9300
O3—C13	1.207 (4)	C13—C14	1.499 (5)
N1—C11	1.279 (5)	C14—H14A	0.9700
N1—N2	1.372 (4)	C14—H14B	0.9700
N2—C12	1.374 (5)	C15—C16	1.507 (5)
N2—C14	1.449 (4)	C15—H15A	0.9700
N3—C13	1.376 (5)	C15—H15B	0.9700
N3—C12	1.402 (4)	C16—C17	1.516 (5)
N3—C15	1.464 (4)	C16—H16A	0.9700
N4—C18	1.488 (4)	C16—H16B	0.9700
N4—C22	1.501 (4)	C17—C18	1.517 (4)
N4—C19	1.504 (4)	C17—H17A	0.9700
N4—H4A	1.04 (4)	C17—H17B	0.9700
N5—C23	1.486 (4)	C18—H18A	0.9700
N5—C20	1.487 (5)	C18—H18B	0.9700
N5—C21	1.489 (4)	C19—C20	1.498 (5)
N5—H5A	1.05 (4)	C19—H19A	0.9700
C1—C2	1.378 (6)	C19—H19B	0.9700
C1—C6	1.385 (5)	C20—H20A	0.9700
C1—H1	0.9300	C20—H20B	0.9700
C2—C3	1.365 (6)	C21—C22	1.501 (5)
C2—H2	0.9300	C21—H21A	0.9700
C3—C4	1.372 (6)	C21—H21B	0.9700
C4—C5	1.378 (6)	C22—H22A	0.9700
C4—H4	0.9300	C22—H22B	0.9700
C5—C6	1.384 (6)	C23—H23A	0.9600
C5—H5	0.9300	C23—H23B	0.9600
C6—C7	1.460 (5)	C23—H23C	0.9600
C7—C8	1.357 (6)	O4—H4C	0.8500
C8—C9	1.402 (5)	O4—H4B	0.8627
C8—H8	0.9300

C7—O1—C10	106.7 (3)	N2—C14—H14A	111.3
C11—N1—N2	116.5 (3)	C13—C14—H14A	111.3
N1—N2—C12	118.9 (3)	N2—C14—H14B	111.3
N1—N2—C14	127.0 (3)	C13—C14—H14B	111.3
C12—N2—C14	112.4 (3)	H14A—C14—H14B	109.2
C13—N3—C12	111.9 (3)	N3—C15—C16	113.7 (3)
C13—N3—C15	125.2 (3)	N3—C15—H15A	108.8
C12—N3—C15	122.4 (3)	C16—C15—H15A	108.8
C18—N4—C22	113.0 (3)	N3—C15—H15B	108.8
C18—N4—C19	110.6 (3)	C16—C15—H15B	108.8
C22—N4—C19	108.9 (3)	H15A—C15—H15B	107.7
C18—N4—H4A	111 (2)	C15—C16—C17	114.7 (3)
C22—N4—H4A	106 (2)	C15—C16—H16A	108.6
C19—N4—H4A	107.1 (18)	C17—C16—H16A	108.6
C23—N5—C20	111.8 (3)	C15—C16—H16B	108.6
C23—N5—C21	112.6 (3)	C17—C16—H16B	108.6
C20—N5—C21	109.1 (3)	H16A—C16—H16B	107.6
C23—N5—H5A	107 (2)	C16—C17—C18	112.1 (3)
C20—N5—H5A	110 (2)	C16—C17—H17A	109.2
C21—N5—H5A	106 (2)	C18—C17—H17A	109.2
C2—C1—C6	120.6 (5)	C16—C17—H17B	109.2
C2—C1—H1	119.7	C18—C17—H17B	109.2
C6—C1—H1	119.7	H17A—C17—H17B	107.9
C3—C2—C1	120.3 (4)	N4—C18—C17	111.5 (3)
C3—C2—H2	119.9	N4—C18—H18A	109.3
C1—C2—H2	119.9	C17—C18—H18A	109.3
C2—C3—C4	120.3 (4)	N4—C18—H18B	109.3
C2—C3—Cl1	120.2 (4)	C17—C18—H18B	109.3
C4—C3—Cl1	119.5 (4)	H18A—C18—H18B	108.0
C3—C4—C5	119.5 (5)	C20—C19—N4	110.8 (3)
C3—C4—H4	120.3	C20—C19—H19A	109.5
C5—C4—H4	120.3	N4—C19—H19A	109.5
C4—C5—C6	121.2 (4)	C20—C19—H19B	109.5
C4—C5—H5	119.4	N4—C19—H19B	109.5
C6—C5—H5	119.4	H19A—C19—H19B	108.1
C5—C6—C1	118.2 (4)	N5—C20—C19	110.0 (3)
C5—C6—C7	120.8 (4)	N5—C20—H20A	109.7
C1—C6—C7	120.9 (4)	C19—C20—H20A	109.7
C8—C7—O1	109.0 (4)	N5—C20—H20B	109.7
C8—C7—C6	133.7 (4)	C19—C20—H20B	109.7
O1—C7—C6	117.2 (4)	H20A—C20—H20B	108.2
C7—C8—C9	107.7 (4)	N5—C21—C22	109.9 (3)
C7—C8—H8	126.1	N5—C21—H21A	109.7
C9—C8—H8	126.1	C22—C21—H21A	109.7
C10—C9—C8	106.7 (4)	N5—C21—H21B	109.7
C10—C9—H9	126.7	C22—C21—H21B	109.7
C8—C9—H9	126.7	H21A—C21—H21B	108.2
C9—C10—O1	110.0 (3)	C21—C22—N4	111.2 (3)
C9—C10—C11	131.0 (4)	C21—C22—H22A	109.4
O1—C10—C11	118.9 (4)	N4—C22—H22A	109.4
N1—C11—C10	121.3 (4)	C21—C22—H22B	109.4
N1—C11—H11	119.4	N4—C22—H22B	109.4
C10—C11—H11	119.4	H22A—C22—H22B	108.0
O2—C12—N2	128.1 (4)	N5—C23—H23A	109.5
O2—C12—N3	125.8 (4)	N5—C23—H23B	109.5
N2—C12—N3	106.1 (3)	H23A—C23—H23B	109.5
O3—C13—N3	124.9 (4)	N5—C23—H23C	109.5
O3—C13—C14	127.9 (4)	H23A—C23—H23C	109.5
N3—C13—C14	107.2 (3)	H23B—C23—H23C	109.5
N2—C14—C13	102.4 (3)	H4C—O4—H4B	108.2

C11—N1—N2—C12	−171.5 (4)	N1—N2—C12—N3	166.0 (3)
C11—N1—N2—C14	−7.7 (5)	C14—N2—C12—N3	−0.1 (4)
C6—C1—C2—C3	1.1 (7)	C13—N3—C12—O2	−179.5 (4)
C1—C2—C3—C4	−0.4 (7)	C15—N3—C12—O2	7.6 (6)
C1—C2—C3—Cl1	178.4 (3)	C13—N3—C12—N2	0.5 (4)
C2—C3—C4—C5	−0.6 (7)	C15—N3—C12—N2	−172.3 (3)
Cl1—C3—C4—C5	−179.4 (3)	C12—N3—C13—O3	−180.0 (4)
C3—C4—C5—C6	1.0 (7)	C15—N3—C13—O3	−7.4 (6)
C4—C5—C6—C1	−0.4 (6)	C12—N3—C13—C14	−0.7 (4)
C4—C5—C6—C7	177.3 (4)	C15—N3—C13—C14	171.9 (3)
C2—C1—C6—C5	−0.7 (6)	N1—N2—C14—C13	−165.1 (3)
C2—C1—C6—C7	−178.4 (4)	C12—N2—C14—C13	−0.3 (4)
C10—O1—C7—C8	0.1 (4)	N3—C13—C14—N2	0.6 (4)
C10—O1—C7—C6	−176.9 (3)	C13—N3—C15—C16	100.9 (4)
C5—C6—C7—C8	−165.5 (5)	C12—N3—C15—C16	−87.3 (4)
C1—C6—C7—C8	12.2 (7)	N3—C15—C16—C17	−61.7 (4)
C5—C6—C7—O1	10.5 (6)	C15—C16—C17—C18	−66.6 (4)
C1—C6—C7—O1	−171.9 (4)	C22—N4—C18—C17	−70.6 (4)
O1—C7—C8—C9	−0.4 (5)	C19—N4—C18—C17	167.0 (3)
C6—C7—C8—C9	175.8 (4)	C16—C17—C18—N4	−173.7 (3)
C7—C8—C9—C10	0.6 (5)	C18—N4—C19—C20	−178.4 (3)
C8—C9—C10—O1	−0.6 (5)	C22—N4—C19—C20	56.9 (4)
C8—C9—C10—C11	175.8 (4)	C23—N5—C20—C19	−174.5 (3)
C7—O1—C10—C9	0.3 (4)	C21—N5—C20—C19	60.4 (4)
C7—O1—C10—C11	−176.6 (3)	N4—C19—C20—N5	−59.7 (4)
N2—N1—C11—C10	177.1 (3)	C23—N5—C21—C22	175.5 (3)
C9—C10—C11—N1	−170.6 (4)	C20—N5—C21—C22	−59.8 (4)
O1—C10—C11—N1	5.5 (6)	N5—C21—C22—N4	58.8 (4)
N1—N2—C12—O2	−13.9 (6)	C18—N4—C22—C21	−179.9 (3)
C14—N2—C12—O2	179.9 (4)	C19—N4—C22—C21	−56.6 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4B···Cl3	0.86	2.40	3.250 (3)	169
O4—H4C···Cl3ⁱ	0.85	2.50	3.250 (3)	148
N5—H5A···Cl2ⁱⁱ	1.05 (4)	1.95 (4)	2.995 (3)	174 (3)
N4—H4A···Cl3	1.04 (4)	2.00 (4)	3.035 (3)	178 (3)

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

Experimental details

Crystal data
Chemical formula	C₂₃H₃₀ClN₅O₃²⁺·2Cl⁻·0.5H₂O
M_r	539.88
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	294
a, b, c (Å)	59.563 (12), 6.8793 (14), 12.831 (2)
β (°)	94.402 (4)
V (Å³)	5241.9 (18)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.39
Crystal size (mm)	0.20 × 0.14 × 0.08

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.725, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	12667, 4629, 2498
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.123, 1.00
No. of reflections	4629
No. of parameters	321
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.28

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4B···Cl3	0.86	2.40	3.250 (3)	169
O4—H4C···Cl3ⁱ	0.85	2.50	3.250 (3)	148
N5—H5A···Cl2ⁱⁱ	1.05 (4)	1.95 (4)	2.995 (3)	174 (3)
N4—H4A···Cl3	1.04 (4)	2.00 (4)	3.035 (3)	178 (3)

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

Acknowledgements

The authors thank Mr Hai-Bin Song at Nankai University for the X-ray crystallographic determination and helpful suggestions.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Matson, P. A., Godlewski, M. S., Quorroz, D. & Guggisberg, Y. (1999). WO Patent 9 955 700. Google Scholar
Pratt, C. M., Singh, S. N., Al-Khalidi, H. R., Brum, J. M., Holroyde, M. J., Marcello, S. R., Schwartz, P. J. & Camm, A. J. (2004). J. Am. Coll. Cardiol. 43, 1211–1216. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 2| February 2011| Page o320

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

1-[4-(3-{[5-(4-Chloro­phen­yl)furan-2-yl]methyl­­idene­amino}-2,5-dioxoimidazol­idin-1-yl)but­yl]-4-methyl­piperazine-1,4-diium dichloride hemihydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1-[4-(3-{[5-(4-Chlorophenyl)furan-2-yl]methylideneamino}-2,5-dioxoimidazolidin-1-yl)butyl]-4-methylpiperazine-1,4-diium dichloride hemihydrate