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In the title compound, C25H28N62+·2Cl-·2H2O, the dihedral angle between the two benz­imidazole groups is 88.42 (4)°. The crystal structure is stabilized by hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803009851/ob6244sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803009851/ob6244Isup2.hkl
Contains datablock I

CCDC reference: 214820

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.049
  • wR factor = 0.154
  • Data-to-parameter ratio = 19.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 28.30 From the CIF: _reflns_number_total 6112 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 6570 Completeness (_total/calc) 93.03% Alert C: < 95% complete
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Comment top

Many benzimidazole compounds are known to possess versatile pharmacological activities, such as antibacterial, antifungal, antihelmintic, antiallergic, antineoplastic, local analgesic, antihistaminic, vasodilator, hypotensive and spasmolytic activities (Carlsson et al., 2002; Del Poeta et al., 1998; Hall et al., 1998). In our previous studies (Çetinkaya et al., 1996; Küçükbay et al., 1995, 2001; Küçükbay & Durmaz, 1997), we also observed that many benzimidazole derivatives have shown considerable antibacterial and antifungal activity against standard strains, viz. Enterococcus faecalis (ATCC 29212), Staphylococcus aureus (ATCC 29213), Escherichia coli (ATCC25922), Pseudomonas aeruginosa (ATCC27853) and, yeast-like fungi Candida albicans and Candida tropicalis. In recent years, particularly bis-benzimidazole compounds have begun to attract particular interest because of their potential use in cancer therapy by DNA binding blocking purposes (Turner & Denny, 1996). The aim of this study was to elucidate the crystal structure of new bis-benzimidazole derivatives and compare with those of the related benzimidazole derivatives reported previously (Çetinkaya et al., 1994; Aydın et al., 1998, 1999; Íngeç et al., 1999; Öztürk et al., 2001).

A view of the title compound, (I), is shown in Fig. 1 and selected geometric parameters are listed in Table 1. In (I), two benzimidazolium rings are connected via atoms C8, C9 and C10. The average bond lengths and angles involving the (N2)C8/C9/C10/(N3) group [C—C = 1.507 (3) Å, C—N = 1.476 (3) Å and C—C—C = 112.1 (6)°] are consistent with those observed in bis(1-methyl-3-ethylbenzimidazolidine-2-ylium) tetrafluoroborate (Aydın et al., 1998). Within the five-membered ring, the bond lengths indicate a delocalized bonding, the N to central C1 and C11 atoms averaging 1.331 (3) Å. In 1-(2-ethoxyethyl)-3-(2-methoxyethyl)benzimidazolium chloride monohydrate (Öztürk et al., 2001), this value is 1.328 (7) Å.

In the molecule, the fused six- and five-membered ring units are essentially planar [maxiumum deviations are 0.022 (2) Å for C6 and 0.026 (2) Å for C14], but the cyano groups of two benzimidazol groups are bent out of plane on opposite sides of the fused rings. The benzimidazol groups are nearly normal to each other, the dihedral angle between their planes being 88.42 (4)°. The short contacts between the molecules and hydrogen bonds, calculated using PARST (Nardelli, 1995), are listed in Table 3.

Experimental top

All experiments were performed under argon using freshly distilled dry solvents. To a solution of 1,1'-propylenedibenzimidazole (1.15 g, 4.17 mmol) in dimethylformamide (5 ml) 3-cyanopropyl chloride (0.8 ml, 8.34 mmol) was added and the mixture was refluxed for 3 h. Then all volatiles were driven off and the obtained crude product was crystallized from EtOH/Et2O (3:1) as a colorless crystals (1.69 g, 84%). M.p.: 392–393 K. 1H NMR (DMSO): δ 2.33 (m, NCH2CH2CH2CN, 4H), 2.78 (t, NCH2CH2CH2CN, 4H), 2.79 (m, NCH2CH2CH2N, 2H), 4.46 (t, NCH2CH2CH2CN, 4H), 4.82 (t, NCH2CH2CH2N, 4H), 7.69–8.23 (m, Ar—H, 8H), 10.54 (s, CH, 2H).13C NMR (DMSO): δ 15.68, 26.37, 29.82, 45.85, 47.48, 109.21, 115.64, 121.44, 128.36, 133.06, 144.89. Analysis calculated for C28H32Cl2N6: C 62.11, H 5.80, N 17.39%; found: C 62.13, H 5.80, N 17.47%.

Refinement top

The H atoms of the water molecules were located from difference maps, and those bound to the C atoms were geometrically positioned. They were allowed to ride on their parent atoms.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 1990) and WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, (I), with the atom-numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.
[Figure 2] Fig. 2. Projection of the crystal structure of (I) along the a axis. Hydrogen bonding is indicated by dotted lines.
3,3'-Bis(3-cyanopropyl)-1,1'-propylenedi(benzimidazolium) dichloride dihyrate top
Crystal data top
C25H28N62+·2Cl·2H2OZ = 2
Mr = 519.47F(000) = 548
Triclinic, P1Dx = 1.304 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.5530 (17) ÅCell parameters from 8119 reflections
b = 11.0533 (18) Åθ = 2.4–28.3°
c = 13.494 (2) ŵ = 0.28 mm1
α = 71.698 (3)°T = 293 K
β = 75.434 (3)°Slab, colorless
γ = 63.279 (2)°0.44 × 0.26 × 0.24 mm
V = 1323.5 (4) Å3
Data collection top
Siemens SMART CCD area-detector
diffractometer
4561 reflections with I > 2σ(I)
Detector resolution: 8.33 pixels mm-1Rint = 0.026
ω scansθmax = 28.3°, θmin = 2.4°
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
h = 1314
Tmin = 0.887, Tmax = 0.936k = 1414
8119 measured reflectionsl = 177
6112 independent reflections
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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154H-atom parameters not refined
S = 1.00 w = 1/[σ2(Fo2) + (0.0902P)2 + 0.219P]
where P = (Fo2 + 2Fc2)/3
6112 reflections(Δ/σ)max = 0.001
316 parametersΔρmax = 0.49 e Å3
0 restraintsΔρmin = 0.30 e Å3
Crystal data top
C25H28N62+·2Cl·2H2Oγ = 63.279 (2)°
Mr = 519.47V = 1323.5 (4) Å3
Triclinic, P1Z = 2
a = 10.5530 (17) ÅMo Kα radiation
b = 11.0533 (18) ŵ = 0.28 mm1
c = 13.494 (2) ÅT = 293 K
α = 71.698 (3)°0.44 × 0.26 × 0.24 mm
β = 75.434 (3)°
Data collection top
Siemens SMART CCD area-detector
diffractometer
6112 independent reflections
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
4561 reflections with I > 2σ(I)
Tmin = 0.887, Tmax = 0.936Rint = 0.026
8119 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.154H-atom parameters not refined
S = 1.00Δρmax = 0.49 e Å3
6112 reflectionsΔρmin = 0.30 e Å3
316 parameters
Special details top

Experimental. 1H-NMR and 13C-NMR spectra were recorded using a Bruker DPX-400 high performance digital FT-NMR (Bruker WM360, Bruker Instruments, Inc., Billercia, USA) spectrometers. Elemental analysis was performed by the elemental analysis laboratory of Tübitak (The Scientific and Technical Research Consul of Turkey) at Ankara (Turkey). Melting point was recorded using an electrothermal melting point apparatus, Electrothermal 9200 (Electrothermal Engineering Ltd., Essex, UK) and are uncorrected.

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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*/Ueq
N10.10057 (15)0.90031 (16)0.38903 (12)0.0428 (4)
N20.12677 (15)0.78637 (14)0.40517 (11)0.0381 (4)
N30.44189 (16)0.66596 (16)0.14148 (11)0.0454 (5)
N40.64901 (16)0.63512 (16)0.04270 (12)0.0458 (5)
N50.5325 (3)0.9738 (3)0.13791 (19)0.0855 (9)
N60.9234 (3)1.0061 (3)0.1195 (2)0.0994 (11)
C10.00551 (18)0.77514 (19)0.40884 (14)0.0423 (5)
C20.04630 (18)1.00040 (18)0.37090 (13)0.0404 (5)
C30.1118 (2)1.1449 (2)0.34932 (15)0.0508 (6)
C40.0243 (3)1.2126 (2)0.33849 (16)0.0587 (7)
C50.1207 (3)1.1391 (2)0.35091 (17)0.0579 (7)
C60.1852 (2)0.9955 (2)0.37441 (15)0.0474 (6)
C70.09840 (17)0.92759 (17)0.38247 (12)0.0376 (5)
C80.26509 (18)0.66833 (19)0.42543 (14)0.0436 (5)
C90.37953 (19)0.6643 (2)0.33081 (14)0.0451 (5)
C100.3302 (2)0.6716 (3)0.23348 (15)0.0544 (7)
C110.57801 (19)0.64014 (19)0.13959 (14)0.0461 (6)
C120.55243 (19)0.65813 (18)0.02259 (14)0.0438 (5)
C130.5707 (2)0.6571 (2)0.12813 (15)0.0521 (6)
C140.4503 (3)0.6809 (2)0.16688 (16)0.0584 (7)
C150.3173 (3)0.7048 (2)0.10379 (16)0.0569 (7)
C160.2997 (2)0.7041 (2)0.00100 (16)0.0524 (6)
C170.4208 (2)0.67908 (18)0.04035 (14)0.0442 (5)
C180.2516 (2)0.9283 (2)0.39298 (16)0.0524 (6)
C190.28770 (19)0.9430 (2)0.28764 (15)0.0473 (6)
C200.4482 (2)0.9799 (2)0.30018 (16)0.0518 (6)
C210.4950 (2)0.9783 (2)0.20819 (18)0.0577 (7)
C220.8033 (2)0.5998 (2)0.01247 (17)0.0551 (6)
C230.8401 (2)0.7197 (2)0.05698 (17)0.0581 (7)
C240.8160 (3)0.8273 (3)0.00065 (19)0.0677 (8)
C250.8761 (3)0.9285 (3)0.0660 (2)0.0743 (9)
O1W0.1555 (2)0.4021 (2)0.43591 (17)0.0937 (8)
O2W0.27927 (19)0.4026 (2)0.67187 (14)0.0796 (7)
Cl10.48420 (5)0.27915 (5)0.45865 (4)0.0565 (2)
Cl20.03459 (5)0.56589 (6)0.21851 (4)0.0632 (2)
H1A0.003860.691350.423270.0508*
H3A0.208711.193390.342550.0609*
H4A0.063041.309380.322540.0705*
H5A0.175531.188700.343060.0694*
H6A0.281160.946990.384270.0569*
H8A0.251780.582100.445350.0524*
H8B0.297460.674550.484160.0524*
H9A0.405650.741900.318670.0541*
H9B0.464120.578920.345650.0541*
H10A0.302970.594580.245970.0653*
H10B0.246270.757430.218230.0653*
H11A0.618550.627290.197820.0553*
H13A0.658700.641240.170020.0625*
H14A0.457500.681090.237050.0701*
H15A0.238860.721540.133630.0683*
H16A0.211720.719510.042910.0628*
H18A0.311691.013380.416860.0628*
H18B0.272160.852890.443700.0628*
H19A0.233520.856350.264980.0568*
H19B0.264331.015790.235310.0568*
H20A0.471820.914310.360500.0622*
H20B0.500421.071930.314490.0622*
H22A0.843560.525120.024110.0662*
H22B0.848360.565150.075930.0662*
H23A0.939800.683250.087190.0698*
H23B0.782590.764780.114460.0698*
H24A0.714170.876110.020310.0812*
H24B0.860820.781090.064610.0812*
H2010.264660.365350.422040.1406*
H2020.122060.443950.359340.1406*
H1010.186990.419370.685840.1194*
H1020.318190.383470.601840.1194*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0386 (7)0.0476 (8)0.0452 (8)0.0178 (6)0.0032 (6)0.0157 (7)
N20.0392 (7)0.0371 (7)0.0367 (7)0.0149 (6)0.0007 (5)0.0110 (5)
N30.0462 (8)0.0489 (9)0.0370 (8)0.0140 (7)0.0026 (6)0.0148 (6)
N40.0462 (8)0.0450 (8)0.0389 (8)0.0119 (7)0.0038 (6)0.0113 (6)
N50.0702 (13)0.1110 (19)0.0733 (14)0.0255 (13)0.0224 (11)0.0252 (13)
N60.132 (2)0.0833 (17)0.0934 (19)0.0559 (17)0.0077 (16)0.0208 (14)
C10.0439 (9)0.0441 (9)0.0434 (9)0.0207 (7)0.0007 (7)0.0153 (7)
C20.0442 (9)0.0423 (9)0.0337 (8)0.0166 (7)0.0011 (7)0.0121 (7)
C30.0564 (11)0.0435 (10)0.0399 (9)0.0107 (8)0.0032 (8)0.0101 (8)
C40.0839 (15)0.0389 (10)0.0458 (11)0.0237 (10)0.0022 (10)0.0099 (8)
C50.0772 (14)0.0570 (12)0.0513 (11)0.0420 (11)0.0083 (10)0.0185 (9)
C60.0503 (10)0.0546 (11)0.0453 (10)0.0285 (8)0.0026 (8)0.0177 (8)
C70.0431 (8)0.0398 (8)0.0302 (8)0.0176 (7)0.0004 (6)0.0111 (6)
C80.0425 (9)0.0419 (9)0.0380 (9)0.0113 (7)0.0043 (7)0.0076 (7)
C90.0414 (9)0.0453 (9)0.0418 (9)0.0122 (7)0.0026 (7)0.0116 (7)
C100.0469 (10)0.0741 (14)0.0442 (10)0.0242 (10)0.0027 (8)0.0234 (9)
C110.0474 (10)0.0471 (10)0.0409 (9)0.0141 (8)0.0056 (7)0.0140 (8)
C120.0499 (10)0.0347 (8)0.0387 (9)0.0105 (7)0.0063 (7)0.0076 (7)
C130.0627 (11)0.0444 (10)0.0381 (9)0.0147 (8)0.0025 (8)0.0088 (8)
C140.0824 (15)0.0489 (11)0.0382 (10)0.0208 (10)0.0135 (10)0.0069 (8)
C150.0695 (13)0.0509 (11)0.0483 (11)0.0207 (10)0.0217 (10)0.0033 (9)
C160.0533 (10)0.0504 (11)0.0482 (10)0.0163 (9)0.0097 (8)0.0093 (8)
C170.0515 (10)0.0382 (9)0.0369 (9)0.0126 (7)0.0058 (7)0.0093 (7)
C180.0404 (9)0.0645 (12)0.0544 (11)0.0222 (9)0.0022 (8)0.0182 (9)
C190.0436 (9)0.0446 (10)0.0521 (10)0.0178 (8)0.0080 (8)0.0076 (8)
C200.0440 (9)0.0537 (11)0.0533 (11)0.0188 (8)0.0104 (8)0.0047 (9)
C210.0445 (10)0.0598 (12)0.0605 (13)0.0168 (9)0.0122 (9)0.0055 (10)
C220.0465 (10)0.0530 (11)0.0535 (11)0.0109 (8)0.0035 (8)0.0125 (9)
C230.0511 (11)0.0640 (13)0.0496 (11)0.0178 (9)0.0018 (9)0.0125 (9)
C240.0686 (14)0.0659 (14)0.0546 (12)0.0161 (11)0.0073 (10)0.0131 (10)
C250.0903 (18)0.0600 (14)0.0698 (16)0.0240 (13)0.0191 (13)0.0141 (12)
O1W0.0837 (13)0.1035 (15)0.0932 (14)0.0528 (12)0.0186 (10)0.0064 (11)
O2W0.0645 (10)0.1148 (15)0.0659 (10)0.0362 (10)0.0095 (8)0.0285 (10)
Cl10.0528 (3)0.0554 (3)0.0500 (3)0.0148 (2)0.0069 (2)0.0081 (2)
Cl20.0503 (3)0.0738 (4)0.0573 (3)0.0211 (3)0.0040 (2)0.0131 (3)
Geometric parameters (Å, º) top
O1W—H2021.0689C19—C201.530 (3)
O1W—H2011.0225C20—C211.454 (3)
O2W—H1020.9791C22—C231.512 (3)
O2W—H1010.8863C23—C241.514 (4)
N1—C21.393 (3)C24—C251.477 (4)
N1—C181.471 (3)C1—H1A0.9300
N1—C11.328 (3)C3—H3A0.9300
N2—C81.474 (3)C4—H4A0.9296
N2—C71.395 (2)C5—H5A0.9298
N2—C11.328 (3)C6—H6A0.9302
N3—C111.328 (3)C8—H8A0.9700
N3—C171.390 (2)C8—H8B0.9700
N3—C101.477 (3)C9—H9A0.9696
N4—C111.338 (2)C9—H9B0.9702
N4—C121.399 (3)C10—H10B0.9697
N4—C221.471 (3)C10—H10A0.9702
N5—C211.138 (4)C11—H11A0.9300
N6—C251.149 (4)C13—H13A0.9298
C2—C31.389 (3)C14—H14A0.9301
C2—C71.393 (3)C15—H15A0.9299
C3—C41.385 (4)C16—H16A0.9301
C4—C51.398 (4)C18—H18B0.9695
C5—C61.380 (3)C18—H18A0.9704
C6—C71.390 (3)C19—H19B0.9700
C8—C91.517 (3)C19—H19A0.9702
C9—C101.497 (3)C20—H20A0.9696
C12—C131.391 (3)C20—H20B0.9703
C12—C171.395 (3)C22—H22A0.9698
C13—C141.380 (4)C22—H22B0.9701
C14—C151.404 (4)C23—H23B0.9697
C15—C161.377 (3)C23—H23A0.9704
C16—C171.387 (3)C24—H24A0.9702
C18—C191.505 (3)C24—H24B0.9699
Cl1···O2W3.391 (2)C10···H16A2.9365
Cl1···O1W3.163 (2)C11···H9B2.7391
Cl2···O1W3.159 (2)C11···H9A2.8407
Cl2···O2Wi3.178 (2)C12···H23B2.9947
Cl1···H8A3.1175C13···H23B3.0314
Cl1···H1022.4520C13···H22A3.0593
Cl1···H9B3.1156C14···H20Bviii3.0105
Cl1···H18Aii2.8856C14···H19Bviii2.9990
Cl1···H3Aii3.0776C15···H19Bviii2.9162
Cl1···H18Bi3.0199C16···H10B3.0353
Cl1···H2012.1942C18···H3A3.0065
Cl1···H20Ai2.7127C20···H6Av2.9363
Cl1···H14Aiii2.8295C21···H6Av2.9565
Cl1···H8Biv2.8930C21···H9Av3.0628
Cl2···H22Bv3.0806C21···H24Av3.0524
Cl2···H24Bv2.8678C22···H13A3.0258
Cl2···H10A3.1094H1A···O1W2.8365
Cl2···H101i2.3306H1A···O1Wi2.4419
Cl2···H2022.1059H1A···H18B2.5789
Cl2···H13Aiii3.0590H1A···H8A2.4645
Cl2···H22Aiii2.8886H3A···H18A2.5077
O1W···Cl13.163 (2)H3A···Cl1xi3.0776
O1W···C1i3.121 (3)H3A···C183.0065
O1W···Cl23.159 (2)H5A···O1Wxii2.9074
O2W···Cl2i3.178 (2)H6A···C93.0795
O2W···Cl13.391 (2)H6A···C20x2.9363
O2W···C11iv3.082 (3)H6A···C21x2.9565
O2W···C9iv3.327 (3)H6A···C83.0286
O1W···H5Avi2.9074H6A···H9A2.3760
O1W···H1A2.8365H6A···H20Ax2.4154
O1W···H18Bi2.6662H8A···Cl13.1175
O1W···H8A2.6550H8A···H2012.4528
O1W···H1Ai2.4419H8A···O1W2.6550
O2W···H11Aiv2.1523H8A···H1A2.4645
O2W···H9Biv2.7525H8A···H1022.4939
N1···C5vii3.361 (3)H8A···H10A2.5792
N2···C4vii3.357 (3)H8B···Cl1iv2.8930
N3···C14iii3.400 (3)H9A···H6A2.3760
N5···C11v3.325 (4)H9A···C112.8407
N5···C24viii3.405 (5)H9A···C21x3.0628
N6···C7ix3.436 (3)H9A···C62.9009
N6···C2ix3.324 (3)H9A···C73.0312
N2···H10B2.5690H9A···H11A2.4914
N4···H24A2.9490H9B···Cl13.1156
N5···H24Aviii2.8214H9B···O2Wiv2.7525
N5···H24Av2.6327H9B···C112.7391
N5···H23Bviii2.8987H9B···H11A2.3237
N6···H10Bix2.5723H10A···H8A2.5792
C1···C5vii3.436 (3)H10A···Cl23.1094
C1···O1Wi3.121 (3)H10B···N22.5690
C1···C4vii3.512 (3)H10B···C73.0205
C1···C103.570 (3)H10B···N6ix2.5723
C2···N6ix3.324 (3)H10B···C163.0353
C2···C7vii3.516 (2)H11A···H22B2.5027
C2···C6vii3.386 (3)H11A···H9B2.3237
C3···C6vii3.592 (3)H11A···H9A2.4914
C3···C7vii3.478 (3)H11A···C92.6470
C4···C1vii3.512 (3)H11A···O2Wiv2.1523
C4···N2vii3.357 (3)H13A···C223.0258
C5···C1vii3.436 (3)H13A···Cl2iii3.0590
C5···N1vii3.361 (3)H14A···Cl1iii2.8295
C6···C2vii3.386 (3)H16A···C102.9365
C6···C21x3.513 (3)H18A···H3A2.5077
C6···C93.457 (3)H18A···Cl1xi2.8856
C6···C3vii3.592 (3)H18A···C32.8900
C7···N6ix3.436 (3)H18A···H20B2.4407
C7···C103.593 (3)H18B···O1Wi2.6662
C7···C3vii3.478 (3)H18B···Cl1i3.0199
C7···C2vii3.516 (2)H18B···H201i2.5026
C9···C63.457 (3)H18B···H1A2.5789
C9···O2Wiv3.327 (3)H18B···H20A2.3634
C10···C73.593 (3)H19B···C14viii2.9990
C10···C13.570 (3)H19B···C15viii2.9162
C11···O2Wiv3.082 (3)H20A···H18B2.3634
C11···C14iii3.591 (3)H20A···H6Av2.4154
C11···N5x3.325 (4)H20A···Cl1i2.7127
C12···C16iii3.525 (3)H20B···H18A2.4407
C12···C15iii3.580 (3)H20B···C14viii3.0105
C13···C17iii3.494 (3)H22A···Cl2iii2.8886
C13···C21viii3.585 (3)H22A···C133.0593
C13···C16iii3.567 (3)H22B···H24B2.4043
C14···C17iii3.554 (3)H22B···H11A2.5027
C14···C11iii3.591 (3)H22B···Cl2x3.0806
C14···N3iii3.400 (3)H23B···C5ix3.0917
C15···C12iii3.580 (3)H23B···C122.9947
C16···C12iii3.525 (3)H23B···C133.0314
C16···C13iii3.567 (3)H23B···N5viii2.8987
C17···C14iii3.554 (3)H24A···N5x2.6327
C17···C13iii3.494 (3)H24A···C21x3.0524
C21···C6v3.513 (3)H24A···N5viii2.8214
C21···C13viii3.585 (3)H24A···N42.9490
C24···N5viii3.405 (5)H24B···Cl2x2.8678
C3···H18A2.8900H24B···H22B2.4043
C5···H23Bix3.0917H101···Cl2i2.3306
C6···H9A2.9009H102···Cl12.4520
C7···H10B3.0205H102···H8A2.4939
C7···H9A3.0312H201···H18Bi2.5026
C8···H6A3.0286H201···Cl12.1942
C9···H6A3.0795H201···H8A2.4528
C9···H11A2.6470H202···Cl22.1059
H201—O1W—H202104.58C7—C6—H6A121.96
H101—O2W—H102110.73N2—C8—H8B109.02
C1—N1—C2108.45 (17)N2—C8—H8A109.02
C2—N1—C18125.72 (16)H8A—C8—H8B107.79
C1—N1—C18125.71 (17)C9—C8—H8A109.03
C1—N2—C8125.06 (16)C9—C8—H8B109.01
C7—N2—C8126.78 (17)C8—C9—H9A109.21
C1—N2—C7108.13 (16)C10—C9—H9B109.18
C11—N3—C17108.14 (16)C8—C9—H9B109.19
C10—N3—C11127.98 (16)C10—C9—H9A109.20
C10—N3—C17123.77 (19)H9A—C9—H9B107.91
C12—N4—C22126.18 (16)C9—C10—H10A109.15
C11—N4—C12107.58 (18)C9—C10—H10B109.17
C11—N4—C22126.05 (18)N3—C10—H10B109.17
N1—C1—N2110.52 (17)N3—C10—H10A109.14
C3—C2—C7122.05 (19)H10A—C10—H10B107.88
N1—C2—C3131.7 (2)N4—C11—H11A124.54
N1—C2—C7106.25 (16)N3—C11—H11A124.54
C2—C3—C4116.1 (2)C14—C13—H13A122.00
C3—C4—C5121.7 (2)C12—C13—H13A122.05
C4—C5—C6122.3 (3)C15—C14—H14A118.94
C5—C6—C7116.1 (2)C13—C14—H14A118.93
N2—C7—C6131.51 (18)C14—C15—H15A119.04
N2—C7—C2106.65 (17)C16—C15—H15A119.06
C2—C7—C6121.81 (17)C15—C16—H16A121.93
N2—C8—C9112.83 (15)C17—C16—H16A121.97
C8—C9—C10112.06 (19)C19—C18—H18A109.14
N3—C10—C9112.2 (2)C19—C18—H18B109.20
N3—C11—N4110.91 (17)H18A—C18—H18B107.88
N4—C12—C17106.53 (16)N1—C18—H18B109.11
N4—C12—C13131.7 (2)N1—C18—H18A109.06
C13—C12—C17121.7 (2)C20—C19—H19A110.17
C12—C13—C14115.9 (2)C18—C19—H19A110.19
C13—C14—C15122.1 (2)C18—C19—H19B110.25
C14—C15—C16121.9 (3)H19A—C19—H19B108.49
C15—C16—C17116.1 (2)C20—C19—H19B110.22
N3—C17—C16130.97 (19)C19—C20—H20B108.79
C12—C17—C16122.18 (18)C19—C20—H20A108.84
N3—C17—C12106.83 (19)H20A—C20—H20B107.71
N1—C18—C19112.35 (17)C21—C20—H20A108.90
C18—C19—C20107.52 (17)C21—C20—H20B108.88
C19—C20—C21113.57 (18)C23—C22—H22A108.62
N5—C21—C20178.0 (3)C23—C22—H22B108.62
N4—C22—C23114.46 (17)H22A—C22—H22B107.59
C22—C23—C24113.54 (19)N4—C22—H22A108.68
C23—C24—C25110.9 (2)N4—C22—H22B108.66
N6—C25—C24178.7 (3)C24—C23—H23A108.81
N2—C1—H1A124.75C22—C23—H23A108.87
N1—C1—H1A124.74C22—C23—H23B108.90
C4—C3—H3A121.92H23A—C23—H23B107.70
C2—C3—H3A121.99C24—C23—H23B108.87
C3—C4—H4A119.11C23—C24—H24B109.47
C5—C4—H4A119.20C23—C24—H24A109.42
C6—C5—H5A118.88H24A—C24—H24B108.04
C4—C5—H5A118.86C25—C24—H24A109.45
C5—C6—H6A121.96C25—C24—H24B109.46
C2—N1—C1—N20.2 (2)C11—N4—C22—C23111.9 (2)
C18—N1—C1—N2175.88 (16)C12—N4—C22—C2373.8 (2)
C1—N1—C2—C3178.39 (19)N1—C2—C3—C4178.15 (18)
C1—N1—C2—C70.79 (19)C7—C2—C3—C40.9 (3)
C18—N1—C2—C32.3 (3)N1—C2—C7—N21.10 (18)
C18—N1—C2—C7175.24 (16)N1—C2—C7—C6177.03 (16)
C1—N1—C18—C1992.4 (2)C3—C2—C7—C60.9 (3)
C2—N1—C18—C1992.2 (2)C3—C2—C7—N2178.98 (16)
C7—N2—C1—N10.6 (2)C2—C3—C4—C51.3 (3)
C8—N2—C1—N1178.67 (15)C3—C4—C5—C60.1 (3)
C1—N2—C7—C21.03 (18)C4—C5—C6—C71.6 (3)
C1—N2—C7—C6176.84 (18)C5—C6—C7—C22.0 (3)
C8—N2—C7—C2179.11 (15)C5—C6—C7—N2179.64 (18)
C8—N2—C7—C61.2 (3)N2—C8—C9—C1052.0 (2)
C1—N2—C8—C9118.3 (2)C8—C9—C10—N3179.30 (18)
C7—N2—C8—C963.9 (2)N4—C12—C13—C14178.2 (2)
C11—N3—C10—C98.3 (3)C17—C12—C13—C141.3 (3)
C17—N3—C10—C9176.08 (18)N4—C12—C17—N31.0 (2)
C10—N3—C11—N4176.1 (2)N4—C12—C17—C16179.53 (18)
C17—N3—C11—N40.1 (2)C13—C12—C17—N3176.65 (17)
C10—N3—C17—C12175.7 (2)C13—C12—C17—C161.9 (3)
C10—N3—C17—C162.7 (3)C12—C13—C14—C150.0 (3)
C11—N3—C17—C120.7 (2)C13—C14—C15—C160.8 (3)
C11—N3—C17—C16179.1 (2)C14—C15—C16—C170.3 (3)
C12—N4—C11—N30.5 (2)C15—C16—C17—C121.1 (3)
C22—N4—C11—N3175.72 (17)C15—C16—C17—N3177.14 (19)
C11—N4—C12—C13176.4 (2)N1—C18—C19—C20176.83 (16)
C11—N4—C12—C170.9 (2)C18—C19—C20—C21171.87 (17)
C22—N4—C12—C131.2 (3)N4—C22—C23—C2472.7 (3)
C22—N4—C12—C17176.10 (17)C22—C23—C24—C25170.5 (2)
Symmetry codes: (i) x, y+1, z+1; (ii) x+1, y1, z; (iii) x+1, y+1, z; (iv) x+1, y+1, z+1; (v) x1, y, z; (vi) x, y1, z; (vii) x, y+2, z+1; (viii) x, y+2, z; (ix) x+1, y+2, z; (x) x+1, y, z; (xi) x1, y+1, z; (xii) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2W—H101···Cl2i0.892.333.178 (2)160
O2W—H102···Cl10.982.453.391 (2)161
O1W—H201···Cl11.022.193.163 (2)158
O1W—H202···Cl21.072.113.159 (2)168
C1—H1A···O1Wi0.932.443.121 (3)130
C10—H10B···N20.972.572.912 (3)101
C10—H10B···N6ix0.972.573.503 (4)161
C11—H11A···O2Wiv0.932.153.082 (3)178
C14—H14A···Cl1iii0.932.833.740 (2)166
C20—H20A···Cl1i0.972.713.666 (2)168
Symmetry codes: (i) x, y+1, z+1; (iii) x+1, y+1, z; (iv) x+1, y+1, z+1; (ix) x+1, y+2, z.

Experimental details

Crystal data
Chemical formulaC25H28N62+·2Cl·2H2O
Mr519.47
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)10.5530 (17), 11.0533 (18), 13.494 (2)
α, β, γ (°)71.698 (3), 75.434 (3), 63.279 (2)
V3)1323.5 (4)
Z2
Radiation typeMo Kα
µ (mm1)0.28
Crystal size (mm)0.44 × 0.26 × 0.24
Data collection
DiffractometerSiemens SMART CCD area-detector
diffractometer
Absorption correctionEmpirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.887, 0.936
No. of measured, independent and
observed [I > 2σ(I)] reflections
8119, 6112, 4561
Rint0.026
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.154, 1.00
No. of reflections6112
No. of parameters316
H-atom treatmentH-atom parameters not refined
Δρmax, Δρmin (e Å3)0.49, 0.30

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), PLATON (Spek, 1990) and WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top
N1—C21.393 (3)N4—C221.471 (3)
N1—C181.471 (3)N5—C211.138 (4)
N1—C11.328 (3)N6—C251.149 (4)
N2—C81.474 (3)C8—C91.517 (3)
N2—C71.395 (2)C9—C101.497 (3)
N2—C11.328 (3)C18—C191.505 (3)
N3—C111.328 (3)C19—C201.530 (3)
N3—C171.390 (2)C20—C211.454 (3)
N3—C101.477 (3)C22—C231.512 (3)
N4—C111.338 (2)C23—C241.514 (4)
N4—C121.399 (3)C24—C251.477 (4)
C7—N2—C8—C963.9 (2)C8—C9—C10—N3179.30 (18)
C17—N3—C10—C9176.08 (18)C18—C19—C20—C21171.87 (17)
N2—C8—C9—C1052.0 (2)C22—C23—C24—C25170.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2W—H101···Cl2i0.892.333.178 (2)160
O2W—H102···Cl10.982.453.391 (2)161
O1W—H201···Cl11.022.193.163 (2)158
O1W—H202···Cl21.072.113.159 (2)168
C1—H1A···O1Wi0.932.443.121 (3)130
C10—H10B···N20.972.572.912 (3)101
C10—H10B···N6ii0.972.573.503 (4)161
C11—H11A···O2Wiii0.932.153.082 (3)178
C14—H14A···Cl1iv0.932.833.740 (2)166
C20—H20A···Cl1i0.972.713.666 (2)168
Symmetry codes: (i) x, y+1, z+1; (ii) x+1, y+2, z; (iii) x+1, y+1, z+1; (iv) x+1, y+1, z.
 

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