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

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ISSN: 2056-9890

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

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[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.]). For background to the bioactivity and applications of the title compound, see: Pratt et al. (2004[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.]). For the preparation of the title compound, see: Matson et al. (1999[Matson, P. A., Godlewski, M. S., Quorroz, D. & Guggisberg, Y. (1999). WO Patent 9 955 700.]).

[Scheme 1]

Experimental

Crystal data
  • C23H30ClN5O32+·2Cl·0.5H2O

  • Mr = 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.725, Tmax = 1.000

  • 12667 measured reflections

  • 4629 independent reflections

  • 2498 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.34 e Å−3

  • Δρmin = −0.28 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


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.

Refinement top

The two water H atoms were located in a difference Fourier map and then refined as riding on the water O atom (0.85 and 0.86 Å). Other H atoms were positioned geometrically and refined using a riding model, with d(C—H) = 0.93 - 0.97 Å and Uiso(H) = 1.2Ueq(C) or 1.5Ueq(Cmethyl).

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
[Figure 1] Fig. 1. The molecular structure of (I) with the atom-numbering scheme and 30% probability displacement ellipsoids.
[Figure 2] 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·0.5H2OF(000) = 2264
Mr = 539.88Dx = 1.368 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2226 reflections
a = 59.563 (12) Åθ = 2.7–27.7°
b = 6.8793 (14) ŵ = 0.39 mm1
c = 12.831 (2) ÅT = 294 K
β = 94.402 (4)°Prism, white
V = 5241.9 (18) Å30.20 × 0.14 × 0.08 mm
Z = 8
Data collection top
Bruker SMART CCD area-detector
diffractometer
4629 independent reflections
Radiation source: fine-focus sealed tube2498 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.059
ϕ and ω scansθmax = 25.0°, θmin = 0.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 7070
Tmin = 0.725, Tmax = 1.000k = 38
12667 measured reflectionsl = 1415
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0367P)2 + 5.8309P]
where P = (Fo2 + 2Fc2)/3
4629 reflections(Δ/σ)max = 0.002
321 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.28 e Å3
Crystal data top
C23H30ClN5O32+·2Cl·0.5H2OV = 5241.9 (18) Å3
Mr = 539.88Z = 8
Monoclinic, C2/cMo Kα radiation
a = 59.563 (12) ŵ = 0.39 mm1
b = 6.8793 (14) ÅT = 294 K
c = 12.831 (2) Å0.20 × 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)
Tmin = 0.725, Tmax = 1.000Rint = 0.059
12667 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.123H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.34 e Å3
4629 reflectionsΔρmin = 0.28 e Å3
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
xyzUiso*/UeqOcc. (<1)
Cl10.23396 (2)0.4537 (2)0.45468 (9)0.0911 (5)
O10.18447 (4)0.8711 (4)0.05974 (19)0.0462 (7)
O20.14878 (5)0.4220 (4)0.1843 (2)0.0589 (8)
O30.12471 (4)0.8338 (4)0.43121 (19)0.0515 (7)
N10.15913 (5)0.7902 (5)0.1069 (2)0.0440 (8)
N20.14652 (5)0.7590 (5)0.1904 (2)0.0448 (8)
N30.13558 (5)0.5894 (4)0.3246 (2)0.0400 (8)
N40.06729 (5)0.5843 (4)0.5197 (2)0.0337 (7)
N50.04067 (5)0.8887 (5)0.6061 (2)0.0390 (8)
C10.22367 (7)0.9011 (7)0.2680 (3)0.0650 (13)
H10.22901.02760.25920.078*
C20.23197 (7)0.7838 (9)0.3432 (3)0.0690 (14)
H20.24300.83080.38400.083*
C30.22404 (7)0.5989 (8)0.3580 (3)0.0594 (12)
C40.20785 (7)0.5277 (7)0.2977 (3)0.0630 (13)
H40.20230.40220.30830.076*
C50.19981 (7)0.6438 (7)0.2213 (3)0.0573 (12)
H50.18900.59460.17970.069*
C60.20750 (6)0.8320 (7)0.2054 (3)0.0485 (11)
C70.19819 (7)0.9568 (6)0.1273 (3)0.0478 (11)
C80.19909 (7)1.1508 (7)0.1081 (3)0.0600 (12)
H80.20731.24180.14290.072*
C90.18542 (7)1.1891 (7)0.0263 (3)0.0574 (12)
H90.18271.30980.00300.069*
C100.17690 (7)1.0172 (6)0.0018 (3)0.0452 (10)
C110.16305 (6)0.9676 (6)0.0845 (3)0.0444 (10)
H110.15681.06620.12250.053*
C120.14429 (6)0.5725 (6)0.2266 (3)0.0439 (10)
C130.13208 (6)0.7804 (6)0.3510 (3)0.0394 (9)
C140.13935 (6)0.9033 (5)0.2631 (3)0.0422 (10)
H14A0.12700.98050.23210.051*
H14B0.15170.98880.28670.051*
C150.13341 (6)0.4226 (6)0.3940 (3)0.0461 (10)
H15A0.13460.46770.46580.055*
H15B0.14580.33400.38570.055*
C160.11156 (6)0.3135 (6)0.3737 (3)0.0464 (10)
H16A0.11180.20140.41970.056*
H16B0.11060.26580.30240.056*
C170.09061 (6)0.4316 (6)0.3897 (3)0.0424 (10)
H17A0.07740.35660.36600.051*
H17B0.09070.54860.34750.051*
C180.08908 (6)0.4875 (6)0.5033 (3)0.0413 (10)
H18A0.09060.37190.54640.050*
H18B0.10140.57470.52480.050*
C190.06381 (6)0.5970 (6)0.6343 (2)0.0426 (10)
H19A0.06430.46760.66440.051*
H19B0.07580.67300.66950.051*
C200.04159 (6)0.6894 (6)0.6511 (3)0.0448 (10)
H20A0.02950.61130.61790.054*
H20B0.03960.69560.72530.054*
C210.04333 (7)0.8767 (6)0.4918 (3)0.0463 (10)
H21A0.04261.00610.46170.056*
H21B0.03120.80020.45810.056*
C220.06551 (6)0.7845 (5)0.4732 (3)0.0413 (10)
H22A0.07760.86470.50410.050*
H22B0.06710.77670.39870.050*
C230.01982 (7)0.9928 (7)0.6300 (3)0.0593 (12)
H23A0.01951.11880.59770.089*
H23B0.01951.00730.70430.089*
H23C0.00690.91960.60340.089*
Cl20.080376 (16)0.89703 (15)0.20687 (7)0.0483 (3)
Cl30.027191 (17)0.36360 (15)0.41881 (7)0.0530 (3)
H4A0.0538 (6)0.507 (5)0.485 (3)0.055 (12)*
H5A0.0542 (7)0.972 (6)0.638 (3)0.069 (13)*
O40.00000.6464 (6)0.25000.0960 (16)
H4C0.00160.57120.19730.115*0.50
H4B0.00680.58260.30110.115*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0934 (10)0.1185 (12)0.0647 (8)0.0178 (9)0.0280 (7)0.0075 (8)
O10.0471 (16)0.0461 (17)0.0460 (15)0.0059 (14)0.0077 (13)0.0043 (14)
O20.081 (2)0.0401 (17)0.0583 (18)0.0067 (16)0.0215 (15)0.0113 (15)
O30.0632 (18)0.0497 (18)0.0428 (15)0.0052 (15)0.0115 (14)0.0118 (14)
N10.049 (2)0.043 (2)0.0403 (18)0.0018 (18)0.0086 (16)0.0052 (17)
N20.059 (2)0.0347 (19)0.0426 (18)0.0017 (18)0.0164 (16)0.0054 (17)
N30.0466 (19)0.0356 (19)0.0383 (17)0.0059 (16)0.0072 (15)0.0029 (16)
N40.044 (2)0.0320 (18)0.0260 (15)0.0009 (17)0.0065 (14)0.0021 (14)
N50.0400 (19)0.037 (2)0.0403 (18)0.0005 (17)0.0081 (15)0.0068 (16)
C10.057 (3)0.077 (4)0.062 (3)0.017 (3)0.011 (2)0.005 (3)
C20.055 (3)0.099 (4)0.055 (3)0.012 (3)0.021 (2)0.003 (3)
C30.053 (3)0.078 (4)0.048 (3)0.011 (3)0.009 (2)0.003 (3)
C40.069 (3)0.065 (3)0.056 (3)0.001 (3)0.014 (2)0.010 (3)
C50.057 (3)0.066 (3)0.051 (3)0.003 (3)0.017 (2)0.007 (2)
C60.038 (2)0.063 (3)0.044 (2)0.000 (2)0.0021 (19)0.011 (2)
C70.045 (3)0.055 (3)0.043 (2)0.007 (2)0.002 (2)0.012 (2)
C80.063 (3)0.055 (3)0.062 (3)0.016 (3)0.004 (2)0.015 (3)
C90.063 (3)0.049 (3)0.060 (3)0.011 (2)0.000 (2)0.000 (2)
C100.045 (3)0.047 (3)0.043 (2)0.004 (2)0.0029 (19)0.003 (2)
C110.045 (2)0.046 (3)0.041 (2)0.000 (2)0.0013 (19)0.003 (2)
C120.042 (2)0.044 (3)0.046 (2)0.003 (2)0.0045 (19)0.002 (2)
C130.037 (2)0.039 (2)0.043 (2)0.005 (2)0.0008 (18)0.004 (2)
C140.046 (2)0.037 (2)0.044 (2)0.000 (2)0.0066 (18)0.008 (2)
C150.048 (3)0.048 (3)0.043 (2)0.018 (2)0.0067 (19)0.008 (2)
C160.055 (3)0.037 (2)0.049 (2)0.007 (2)0.013 (2)0.002 (2)
C170.047 (2)0.042 (2)0.039 (2)0.001 (2)0.0049 (18)0.0055 (19)
C180.043 (2)0.046 (2)0.036 (2)0.007 (2)0.0035 (18)0.0026 (19)
C190.061 (3)0.043 (2)0.0250 (18)0.003 (2)0.0079 (17)0.0050 (18)
C200.056 (3)0.045 (3)0.035 (2)0.007 (2)0.0135 (19)0.001 (2)
C210.060 (3)0.042 (3)0.037 (2)0.007 (2)0.0073 (19)0.001 (2)
C220.058 (3)0.033 (2)0.034 (2)0.002 (2)0.0128 (18)0.0069 (18)
C230.049 (3)0.066 (3)0.064 (3)0.008 (2)0.017 (2)0.016 (3)
Cl20.0508 (6)0.0441 (6)0.0489 (6)0.0031 (5)0.0043 (5)0.0066 (5)
Cl30.0545 (7)0.0547 (7)0.0496 (6)0.0077 (6)0.0021 (5)0.0077 (5)
O40.156 (5)0.046 (3)0.086 (3)0.0000.014 (3)0.000
Geometric parameters (Å, º) top
Cl1—C31.732 (4)C9—C101.347 (5)
O1—C71.370 (4)C9—H90.9300
O1—C101.375 (4)C10—C111.434 (5)
O2—C121.208 (4)C11—H110.9300
O3—C131.207 (4)C13—C141.499 (5)
N1—C111.279 (5)C14—H14A0.9700
N1—N21.372 (4)C14—H14B0.9700
N2—C121.374 (5)C15—C161.507 (5)
N2—C141.449 (4)C15—H15A0.9700
N3—C131.376 (5)C15—H15B0.9700
N3—C121.402 (4)C16—C171.516 (5)
N3—C151.464 (4)C16—H16A0.9700
N4—C181.488 (4)C16—H16B0.9700
N4—C221.501 (4)C17—C181.517 (4)
N4—C191.504 (4)C17—H17A0.9700
N4—H4A1.04 (4)C17—H17B0.9700
N5—C231.486 (4)C18—H18A0.9700
N5—C201.487 (5)C18—H18B0.9700
N5—C211.489 (4)C19—C201.498 (5)
N5—H5A1.05 (4)C19—H19A0.9700
C1—C21.378 (6)C19—H19B0.9700
C1—C61.385 (5)C20—H20A0.9700
C1—H10.9300C20—H20B0.9700
C2—C31.365 (6)C21—C221.501 (5)
C2—H20.9300C21—H21A0.9700
C3—C41.372 (6)C21—H21B0.9700
C4—C51.378 (6)C22—H22A0.9700
C4—H40.9300C22—H22B0.9700
C5—C61.384 (6)C23—H23A0.9600
C5—H50.9300C23—H23B0.9600
C6—C71.460 (5)C23—H23C0.9600
C7—C81.357 (6)O4—H4C0.8500
C8—C91.402 (5)O4—H4B0.8627
C8—H80.9300
C7—O1—C10106.7 (3)N2—C14—H14A111.3
C11—N1—N2116.5 (3)C13—C14—H14A111.3
N1—N2—C12118.9 (3)N2—C14—H14B111.3
N1—N2—C14127.0 (3)C13—C14—H14B111.3
C12—N2—C14112.4 (3)H14A—C14—H14B109.2
C13—N3—C12111.9 (3)N3—C15—C16113.7 (3)
C13—N3—C15125.2 (3)N3—C15—H15A108.8
C12—N3—C15122.4 (3)C16—C15—H15A108.8
C18—N4—C22113.0 (3)N3—C15—H15B108.8
C18—N4—C19110.6 (3)C16—C15—H15B108.8
C22—N4—C19108.9 (3)H15A—C15—H15B107.7
C18—N4—H4A111 (2)C15—C16—C17114.7 (3)
C22—N4—H4A106 (2)C15—C16—H16A108.6
C19—N4—H4A107.1 (18)C17—C16—H16A108.6
C23—N5—C20111.8 (3)C15—C16—H16B108.6
C23—N5—C21112.6 (3)C17—C16—H16B108.6
C20—N5—C21109.1 (3)H16A—C16—H16B107.6
C23—N5—H5A107 (2)C16—C17—C18112.1 (3)
C20—N5—H5A110 (2)C16—C17—H17A109.2
C21—N5—H5A106 (2)C18—C17—H17A109.2
C2—C1—C6120.6 (5)C16—C17—H17B109.2
C2—C1—H1119.7C18—C17—H17B109.2
C6—C1—H1119.7H17A—C17—H17B107.9
C3—C2—C1120.3 (4)N4—C18—C17111.5 (3)
C3—C2—H2119.9N4—C18—H18A109.3
C1—C2—H2119.9C17—C18—H18A109.3
C2—C3—C4120.3 (4)N4—C18—H18B109.3
C2—C3—Cl1120.2 (4)C17—C18—H18B109.3
C4—C3—Cl1119.5 (4)H18A—C18—H18B108.0
C3—C4—C5119.5 (5)C20—C19—N4110.8 (3)
C3—C4—H4120.3C20—C19—H19A109.5
C5—C4—H4120.3N4—C19—H19A109.5
C4—C5—C6121.2 (4)C20—C19—H19B109.5
C4—C5—H5119.4N4—C19—H19B109.5
C6—C5—H5119.4H19A—C19—H19B108.1
C5—C6—C1118.2 (4)N5—C20—C19110.0 (3)
C5—C6—C7120.8 (4)N5—C20—H20A109.7
C1—C6—C7120.9 (4)C19—C20—H20A109.7
C8—C7—O1109.0 (4)N5—C20—H20B109.7
C8—C7—C6133.7 (4)C19—C20—H20B109.7
O1—C7—C6117.2 (4)H20A—C20—H20B108.2
C7—C8—C9107.7 (4)N5—C21—C22109.9 (3)
C7—C8—H8126.1N5—C21—H21A109.7
C9—C8—H8126.1C22—C21—H21A109.7
C10—C9—C8106.7 (4)N5—C21—H21B109.7
C10—C9—H9126.7C22—C21—H21B109.7
C8—C9—H9126.7H21A—C21—H21B108.2
C9—C10—O1110.0 (3)C21—C22—N4111.2 (3)
C9—C10—C11131.0 (4)C21—C22—H22A109.4
O1—C10—C11118.9 (4)N4—C22—H22A109.4
N1—C11—C10121.3 (4)C21—C22—H22B109.4
N1—C11—H11119.4N4—C22—H22B109.4
C10—C11—H11119.4H22A—C22—H22B108.0
O2—C12—N2128.1 (4)N5—C23—H23A109.5
O2—C12—N3125.8 (4)N5—C23—H23B109.5
N2—C12—N3106.1 (3)H23A—C23—H23B109.5
O3—C13—N3124.9 (4)N5—C23—H23C109.5
O3—C13—C14127.9 (4)H23A—C23—H23C109.5
N3—C13—C14107.2 (3)H23B—C23—H23C109.5
N2—C14—C13102.4 (3)H4C—O4—H4B108.2
C11—N1—N2—C12171.5 (4)N1—N2—C12—N3166.0 (3)
C11—N1—N2—C147.7 (5)C14—N2—C12—N30.1 (4)
C6—C1—C2—C31.1 (7)C13—N3—C12—O2179.5 (4)
C1—C2—C3—C40.4 (7)C15—N3—C12—O27.6 (6)
C1—C2—C3—Cl1178.4 (3)C13—N3—C12—N20.5 (4)
C2—C3—C4—C50.6 (7)C15—N3—C12—N2172.3 (3)
Cl1—C3—C4—C5179.4 (3)C12—N3—C13—O3180.0 (4)
C3—C4—C5—C61.0 (7)C15—N3—C13—O37.4 (6)
C4—C5—C6—C10.4 (6)C12—N3—C13—C140.7 (4)
C4—C5—C6—C7177.3 (4)C15—N3—C13—C14171.9 (3)
C2—C1—C6—C50.7 (6)N1—N2—C14—C13165.1 (3)
C2—C1—C6—C7178.4 (4)C12—N2—C14—C130.3 (4)
C10—O1—C7—C80.1 (4)N3—C13—C14—N20.6 (4)
C10—O1—C7—C6176.9 (3)C13—N3—C15—C16100.9 (4)
C5—C6—C7—C8165.5 (5)C12—N3—C15—C1687.3 (4)
C1—C6—C7—C812.2 (7)N3—C15—C16—C1761.7 (4)
C5—C6—C7—O110.5 (6)C15—C16—C17—C1866.6 (4)
C1—C6—C7—O1171.9 (4)C22—N4—C18—C1770.6 (4)
O1—C7—C8—C90.4 (5)C19—N4—C18—C17167.0 (3)
C6—C7—C8—C9175.8 (4)C16—C17—C18—N4173.7 (3)
C7—C8—C9—C100.6 (5)C18—N4—C19—C20178.4 (3)
C8—C9—C10—O10.6 (5)C22—N4—C19—C2056.9 (4)
C8—C9—C10—C11175.8 (4)C23—N5—C20—C19174.5 (3)
C7—O1—C10—C90.3 (4)C21—N5—C20—C1960.4 (4)
C7—O1—C10—C11176.6 (3)N4—C19—C20—N559.7 (4)
N2—N1—C11—C10177.1 (3)C23—N5—C21—C22175.5 (3)
C9—C10—C11—N1170.6 (4)C20—N5—C21—C2259.8 (4)
O1—C10—C11—N15.5 (6)N5—C21—C22—N458.8 (4)
N1—N2—C12—O213.9 (6)C18—N4—C22—C21179.9 (3)
C14—N2—C12—O2179.9 (4)C19—N4—C22—C2156.6 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4B···Cl30.862.403.250 (3)169
O4—H4C···Cl3i0.852.503.250 (3)148
N5—H5A···Cl2ii1.05 (4)1.95 (4)2.995 (3)174 (3)
N4—H4A···Cl31.04 (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 formulaC23H30ClN5O32+·2Cl·0.5H2O
Mr539.88
Crystal system, space groupMonoclinic, C2/c
Temperature (K)294
a, b, c (Å)59.563 (12), 6.8793 (14), 12.831 (2)
β (°) 94.402 (4)
V3)5241.9 (18)
Z8
Radiation typeMo Kα
µ (mm1)0.39
Crystal size (mm)0.20 × 0.14 × 0.08
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.725, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
12667, 4629, 2498
Rint0.059
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.123, 1.00
No. of reflections4629
No. of parameters321
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
O4—H4B···Cl30.862.403.250 (3)169
O4—H4C···Cl3i0.852.503.250 (3)148
N5—H5A···Cl2ii1.05 (4)1.95 (4)2.995 (3)174 (3)
N4—H4A···Cl31.04 (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

First citationAllen, 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
First citationBruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationMatson, P. A., Godlewski, M. S., Quorroz, D. & Guggisberg, Y. (1999). WO Patent 9 955 700.  Google Scholar
First citationPratt, 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
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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