3,3'-Bis(3-cyano­propyl)-1,1'-propyl­enedi­(benzimidazolium) dichloride dihydrate

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.

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


 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

---

S1. Comment

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.

S2. Experimental

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%.

S3. Refinement

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

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

	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.
	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

Crystal data

C25H28N6^2+·2Cl^−·2H2O	Z = 2
Mr = 519.47	F(000) = 548
Triclinic, P1	Dx = 1.304 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.5530 (17) Å	Cell parameters from 8119 reflections
b = 11.0533 (18) Å	θ = 2.4–28.3°
c = 13.494 (2) Å	µ = 0.28 mm^−1
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) Å^3

Data collection

Siemens SMART CCD area-detector diffractometer	4561 reflections with I > 2σ(I)
Detector resolution: 8.33 pixels mm^-1	Rint = 0.026
ω scans	θmax = 28.3°, θmin = 2.4°
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	h = −13→14
Tmin = 0.887, Tmax = 0.936	k = −14→14
8119 measured reflections	l = −17→7
6112 independent reflections

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.154	H-atom parameters not refined
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0902P)^2 + 0.219P] where P = (Fo^2 + 2Fc^2)/3
6112 reflections	(Δ/σ)max = 0.001
316 parameters	Δρmax = 0.49 e Å^−3
0 restraints	Δρmin = −0.30 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	−0.10057 (15)	0.90031 (16)	0.38903 (12)	0.0428 (4)
N2	0.12677 (15)	0.78637 (14)	0.40517 (11)	0.0381 (4)
N3	0.44189 (16)	0.66596 (16)	0.14148 (11)	0.0454 (5)
N4	0.64901 (16)	0.63512 (16)	0.04270 (12)	0.0458 (5)
N5	−0.5325 (3)	0.9738 (3)	0.13791 (19)	0.0855 (9)
N6	0.9234 (3)	1.0061 (3)	−0.1195 (2)	0.0994 (11)
C1	0.00551 (18)	0.77514 (19)	0.40884 (14)	0.0423 (5)
C2	−0.04630 (18)	1.00040 (18)	0.37090 (13)	0.0404 (5)
C3	−0.1118 (2)	1.1449 (2)	0.34932 (15)	0.0508 (6)
C4	−0.0243 (3)	1.2126 (2)	0.33849 (16)	0.0587 (7)
C5	0.1207 (3)	1.1391 (2)	0.35091 (17)	0.0579 (7)
C6	0.1852 (2)	0.9955 (2)	0.37441 (15)	0.0474 (6)
C7	0.09840 (17)	0.92759 (17)	0.38247 (12)	0.0376 (5)
C8	0.26509 (18)	0.66833 (19)	0.42543 (14)	0.0436 (5)
C9	0.37953 (19)	0.6643 (2)	0.33081 (14)	0.0451 (5)
C10	0.3302 (2)	0.6716 (3)	0.23348 (15)	0.0544 (7)
C11	0.57801 (19)	0.64014 (19)	0.13959 (14)	0.0461 (6)
C12	0.55243 (19)	0.65813 (18)	−0.02259 (14)	0.0438 (5)
C13	0.5707 (2)	0.6571 (2)	−0.12813 (15)	0.0521 (6)
C14	0.4503 (3)	0.6809 (2)	−0.16688 (16)	0.0584 (7)
C15	0.3173 (3)	0.7048 (2)	−0.10379 (16)	0.0569 (7)
C16	0.2997 (2)	0.7041 (2)	0.00100 (16)	0.0524 (6)
C17	0.4208 (2)	0.67908 (18)	0.04035 (14)	0.0442 (5)
C18	−0.2516 (2)	0.9283 (2)	0.39298 (16)	0.0524 (6)
C19	−0.28770 (19)	0.9430 (2)	0.28764 (15)	0.0473 (6)
C20	−0.4482 (2)	0.9799 (2)	0.30018 (16)	0.0518 (6)
C21	−0.4950 (2)	0.9783 (2)	0.20819 (18)	0.0577 (7)
C22	0.8033 (2)	0.5998 (2)	0.01247 (17)	0.0551 (6)
C23	0.8401 (2)	0.7197 (2)	−0.05698 (17)	0.0581 (7)
C24	0.8160 (3)	0.8273 (3)	0.00065 (19)	0.0677 (8)
C25	0.8761 (3)	0.9285 (3)	−0.0660 (2)	0.0743 (9)
O1W	0.1555 (2)	0.4021 (2)	0.43591 (17)	0.0937 (8)
O2W	0.27927 (19)	0.4026 (2)	0.67187 (14)	0.0796 (7)
Cl1	0.48420 (5)	0.27915 (5)	0.45865 (4)	0.0565 (2)
Cl2	0.03459 (5)	0.56589 (6)	0.21851 (4)	0.0632 (2)
H1A	−0.00386	0.69135	0.42327	0.0508*
H3A	−0.20871	1.19339	0.34255	0.0609*
H4A	−0.06304	1.30938	0.32254	0.0705*
H5A	0.17553	1.18870	0.34306	0.0694*
H6A	0.28116	0.94699	0.38427	0.0569*
H8A	0.25178	0.58210	0.44535	0.0524*
H8B	0.29746	0.67455	0.48416	0.0524*
H9A	0.40565	0.74190	0.31867	0.0541*
H9B	0.46412	0.57892	0.34565	0.0541*
H10A	0.30297	0.59458	0.24597	0.0653*
H10B	0.24627	0.75743	0.21823	0.0653*
H11A	0.61855	0.62729	0.19782	0.0553*
H13A	0.65870	0.64124	−0.17002	0.0625*
H14A	0.45750	0.68109	−0.23705	0.0701*
H15A	0.23886	0.72154	−0.13363	0.0683*
H16A	0.21172	0.71951	0.04291	0.0628*
H18A	−0.31169	1.01338	0.41686	0.0628*
H18B	−0.27216	0.85289	0.44370	0.0628*
H19A	−0.23352	0.85635	0.26498	0.0568*
H19B	−0.26433	1.01579	0.23531	0.0568*
H20A	−0.47182	0.91431	0.36050	0.0622*
H20B	−0.50042	1.07193	0.31449	0.0622*
H22A	0.84356	0.52512	−0.02411	0.0662*
H22B	0.84836	0.56515	0.07593	0.0662*
H23A	0.93980	0.68325	−0.08719	0.0698*
H23B	0.78259	0.76478	−0.11446	0.0698*
H24A	0.71417	0.87611	0.02031	0.0812*
H24B	0.86082	0.78109	0.06461	0.0812*
H201	0.26466	0.36535	0.42204	0.1406*
H202	0.12206	0.44395	0.35934	0.1406*
H101	0.18699	0.41937	0.68584	0.1194*
H102	0.31819	0.38347	0.60184	0.1194*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0386 (7)	0.0476 (8)	0.0452 (8)	−0.0178 (6)	−0.0032 (6)	−0.0157 (7)
N2	0.0392 (7)	0.0371 (7)	0.0367 (7)	−0.0149 (6)	−0.0007 (5)	−0.0110 (5)
N3	0.0462 (8)	0.0489 (9)	0.0370 (8)	−0.0140 (7)	−0.0026 (6)	−0.0148 (6)
N4	0.0462 (8)	0.0450 (8)	0.0389 (8)	−0.0119 (7)	−0.0038 (6)	−0.0113 (6)
N5	0.0702 (13)	0.1110 (19)	0.0733 (14)	−0.0255 (13)	−0.0224 (11)	−0.0252 (13)
N6	0.132 (2)	0.0833 (17)	0.0934 (19)	−0.0559 (17)	−0.0077 (16)	−0.0208 (14)
C1	0.0439 (9)	0.0441 (9)	0.0434 (9)	−0.0207 (7)	−0.0007 (7)	−0.0153 (7)
C2	0.0442 (9)	0.0423 (9)	0.0337 (8)	−0.0166 (7)	−0.0011 (7)	−0.0121 (7)
C3	0.0564 (11)	0.0435 (10)	0.0399 (9)	−0.0107 (8)	−0.0032 (8)	−0.0101 (8)
C4	0.0839 (15)	0.0389 (10)	0.0458 (11)	−0.0237 (10)	0.0022 (10)	−0.0099 (8)
C5	0.0772 (14)	0.0570 (12)	0.0513 (11)	−0.0420 (11)	0.0083 (10)	−0.0185 (9)
C6	0.0503 (10)	0.0546 (11)	0.0453 (10)	−0.0285 (8)	0.0026 (8)	−0.0177 (8)
C7	0.0431 (8)	0.0398 (8)	0.0302 (8)	−0.0176 (7)	0.0004 (6)	−0.0111 (6)
C8	0.0425 (9)	0.0419 (9)	0.0380 (9)	−0.0113 (7)	−0.0043 (7)	−0.0076 (7)
C9	0.0414 (9)	0.0453 (9)	0.0418 (9)	−0.0122 (7)	−0.0026 (7)	−0.0116 (7)
C10	0.0469 (10)	0.0741 (14)	0.0442 (10)	−0.0242 (10)	0.0027 (8)	−0.0234 (9)
C11	0.0474 (10)	0.0471 (10)	0.0409 (9)	−0.0141 (8)	−0.0056 (7)	−0.0140 (8)
C12	0.0499 (10)	0.0347 (8)	0.0387 (9)	−0.0105 (7)	−0.0063 (7)	−0.0076 (7)
C13	0.0627 (11)	0.0444 (10)	0.0381 (9)	−0.0147 (8)	−0.0025 (8)	−0.0088 (8)
C14	0.0824 (15)	0.0489 (11)	0.0382 (10)	−0.0208 (10)	−0.0135 (10)	−0.0069 (8)
C15	0.0695 (13)	0.0509 (11)	0.0483 (11)	−0.0207 (10)	−0.0217 (10)	−0.0033 (9)
C16	0.0533 (10)	0.0504 (11)	0.0482 (10)	−0.0163 (9)	−0.0097 (8)	−0.0093 (8)
C17	0.0515 (10)	0.0382 (9)	0.0369 (9)	−0.0126 (7)	−0.0058 (7)	−0.0093 (7)
C18	0.0404 (9)	0.0645 (12)	0.0544 (11)	−0.0222 (9)	−0.0022 (8)	−0.0182 (9)
C19	0.0436 (9)	0.0446 (10)	0.0521 (10)	−0.0178 (8)	−0.0080 (8)	−0.0076 (8)
C20	0.0440 (9)	0.0537 (11)	0.0533 (11)	−0.0188 (8)	−0.0104 (8)	−0.0047 (9)
C21	0.0445 (10)	0.0598 (12)	0.0605 (13)	−0.0168 (9)	−0.0122 (9)	−0.0055 (10)
C22	0.0465 (10)	0.0530 (11)	0.0535 (11)	−0.0109 (8)	−0.0035 (8)	−0.0125 (9)
C23	0.0511 (11)	0.0640 (13)	0.0496 (11)	−0.0178 (9)	−0.0018 (9)	−0.0125 (9)
C24	0.0686 (14)	0.0659 (14)	0.0546 (12)	−0.0161 (11)	−0.0073 (10)	−0.0131 (10)
C25	0.0903 (18)	0.0600 (14)	0.0698 (16)	−0.0240 (13)	−0.0191 (13)	−0.0141 (12)
O1W	0.0837 (13)	0.1035 (15)	0.0932 (14)	−0.0528 (12)	−0.0186 (10)	0.0064 (11)
O2W	0.0645 (10)	0.1148 (15)	0.0659 (10)	−0.0362 (10)	−0.0095 (8)	−0.0285 (10)
Cl1	0.0528 (3)	0.0554 (3)	0.0500 (3)	−0.0148 (2)	−0.0069 (2)	−0.0081 (2)
Cl2	0.0503 (3)	0.0738 (4)	0.0573 (3)	−0.0211 (3)	−0.0040 (2)	−0.0131 (3)

Geometric parameters (Å, º)

O1W—H202	1.0689	C19—C20	1.530 (3)
O1W—H201	1.0225	C20—C21	1.454 (3)
O2W—H102	0.9791	C22—C23	1.512 (3)
O2W—H101	0.8863	C23—C24	1.514 (4)
N1—C2	1.393 (3)	C24—C25	1.477 (4)
N1—C18	1.471 (3)	C1—H1A	0.9300
N1—C1	1.328 (3)	C3—H3A	0.9300
N2—C8	1.474 (3)	C4—H4A	0.9296
N2—C7	1.395 (2)	C5—H5A	0.9298
N2—C1	1.328 (3)	C6—H6A	0.9302
N3—C11	1.328 (3)	C8—H8A	0.9700
N3—C17	1.390 (2)	C8—H8B	0.9700
N3—C10	1.477 (3)	C9—H9A	0.9696
N4—C11	1.338 (2)	C9—H9B	0.9702
N4—C12	1.399 (3)	C10—H10B	0.9697
N4—C22	1.471 (3)	C10—H10A	0.9702
N5—C21	1.138 (4)	C11—H11A	0.9300
N6—C25	1.149 (4)	C13—H13A	0.9298
C2—C3	1.389 (3)	C14—H14A	0.9301
C2—C7	1.393 (3)	C15—H15A	0.9299
C3—C4	1.385 (4)	C16—H16A	0.9301
C4—C5	1.398 (4)	C18—H18B	0.9695
C5—C6	1.380 (3)	C18—H18A	0.9704
C6—C7	1.390 (3)	C19—H19B	0.9700
C8—C9	1.517 (3)	C19—H19A	0.9702
C9—C10	1.497 (3)	C20—H20A	0.9696
C12—C13	1.391 (3)	C20—H20B	0.9703
C12—C17	1.395 (3)	C22—H22A	0.9698
C13—C14	1.380 (4)	C22—H22B	0.9701
C14—C15	1.404 (4)	C23—H23B	0.9697
C15—C16	1.377 (3)	C23—H23A	0.9704
C16—C17	1.387 (3)	C24—H24A	0.9702
C18—C19	1.505 (3)	C24—H24B	0.9699
Cl1···O2W	3.391 (2)	C10···H16A	2.9365
Cl1···O1W	3.163 (2)	C11···H9B	2.7391
Cl2···O1W	3.159 (2)	C11···H9A	2.8407
Cl2···O2W^i	3.178 (2)	C12···H23B	2.9947
Cl1···H8A	3.1175	C13···H23B	3.0314
Cl1···H102	2.4520	C13···H22A	3.0593
Cl1···H9B	3.1156	C14···H20B^viii	3.0105
Cl1···H18A^ii	2.8856	C14···H19B^viii	2.9990
Cl1···H3A^ii	3.0776	C15···H19B^viii	2.9162
Cl1···H18B^i	3.0199	C16···H10B	3.0353
Cl1···H201	2.1942	C18···H3A	3.0065
Cl1···H20A^i	2.7127	C20···H6A^v	2.9363
Cl1···H14A^iii	2.8295	C21···H6A^v	2.9565
Cl1···H8B^iv	2.8930	C21···H9A^v	3.0628
Cl2···H22B^v	3.0806	C21···H24A^v	3.0524
Cl2···H24B^v	2.8678	C22···H13A	3.0258
Cl2···H10A	3.1094	H1A···O1W	2.8365
Cl2···H101^i	2.3306	H1A···O1W^i	2.4419
Cl2···H202	2.1059	H1A···H18B	2.5789
Cl2···H13A^iii	3.0590	H1A···H8A	2.4645
Cl2···H22A^iii	2.8886	H3A···H18A	2.5077
O1W···Cl1	3.163 (2)	H3A···Cl1^xi	3.0776
O1W···C1^i	3.121 (3)	H3A···C18	3.0065
O1W···Cl2	3.159 (2)	H5A···O1W^xii	2.9074
O2W···Cl2^i	3.178 (2)	H6A···C9	3.0795
O2W···Cl1	3.391 (2)	H6A···C20^x	2.9363
O2W···C11^iv	3.082 (3)	H6A···C21^x	2.9565
O2W···C9^iv	3.327 (3)	H6A···C8	3.0286
O1W···H5A^vi	2.9074	H6A···H9A	2.3760
O1W···H1A	2.8365	H6A···H20A^x	2.4154
O1W···H18B^i	2.6662	H8A···Cl1	3.1175
O1W···H8A	2.6550	H8A···H201	2.4528
O1W···H1A^i	2.4419	H8A···O1W	2.6550
O2W···H11A^iv	2.1523	H8A···H1A	2.4645
O2W···H9B^iv	2.7525	H8A···H102	2.4939
N1···C5^vii	3.361 (3)	H8A···H10A	2.5792
N2···C4^vii	3.357 (3)	H8B···Cl1^iv	2.8930
N3···C14^iii	3.400 (3)	H9A···H6A	2.3760
N5···C11^v	3.325 (4)	H9A···C11	2.8407
N5···C24^viii	3.405 (5)	H9A···C21^x	3.0628
N6···C7^ix	3.436 (3)	H9A···C6	2.9009
N6···C2^ix	3.324 (3)	H9A···C7	3.0312
N2···H10B	2.5690	H9A···H11A	2.4914
N4···H24A	2.9490	H9B···Cl1	3.1156
N5···H24A^viii	2.8214	H9B···O2W^iv	2.7525
N5···H24A^v	2.6327	H9B···C11	2.7391
N5···H23B^viii	2.8987	H9B···H11A	2.3237
N6···H10B^ix	2.5723	H10A···H8A	2.5792
C1···C5^vii	3.436 (3)	H10A···Cl2	3.1094
C1···O1W^i	3.121 (3)	H10B···N2	2.5690
C1···C4^vii	3.512 (3)	H10B···C7	3.0205
C1···C10	3.570 (3)	H10B···N6^ix	2.5723
C2···N6^ix	3.324 (3)	H10B···C16	3.0353
C2···C7^vii	3.516 (2)	H11A···H22B	2.5027
C2···C6^vii	3.386 (3)	H11A···H9B	2.3237
C3···C6^vii	3.592 (3)	H11A···H9A	2.4914
C3···C7^vii	3.478 (3)	H11A···C9	2.6470
C4···C1^vii	3.512 (3)	H11A···O2W^iv	2.1523
C4···N2^vii	3.357 (3)	H13A···C22	3.0258
C5···C1^vii	3.436 (3)	H13A···Cl2^iii	3.0590
C5···N1^vii	3.361 (3)	H14A···Cl1^iii	2.8295
C6···C2^vii	3.386 (3)	H16A···C10	2.9365
C6···C21^x	3.513 (3)	H18A···H3A	2.5077
C6···C9	3.457 (3)	H18A···Cl1^xi	2.8856
C6···C3^vii	3.592 (3)	H18A···C3	2.8900
C7···N6^ix	3.436 (3)	H18A···H20B	2.4407
C7···C10	3.593 (3)	H18B···O1W^i	2.6662
C7···C3^vii	3.478 (3)	H18B···Cl1^i	3.0199
C7···C2^vii	3.516 (2)	H18B···H201^i	2.5026
C9···C6	3.457 (3)	H18B···H1A	2.5789
C9···O2W^iv	3.327 (3)	H18B···H20A	2.3634
C10···C7	3.593 (3)	H19B···C14^viii	2.9990
C10···C1	3.570 (3)	H19B···C15^viii	2.9162
C11···O2W^iv	3.082 (3)	H20A···H18B	2.3634
C11···C14^iii	3.591 (3)	H20A···H6A^v	2.4154
C11···N5^x	3.325 (4)	H20A···Cl1^i	2.7127
C12···C16^iii	3.525 (3)	H20B···H18A	2.4407
C12···C15^iii	3.580 (3)	H20B···C14^viii	3.0105
C13···C17^iii	3.494 (3)	H22A···Cl2^iii	2.8886
C13···C21^viii	3.585 (3)	H22A···C13	3.0593
C13···C16^iii	3.567 (3)	H22B···H24B	2.4043
C14···C17^iii	3.554 (3)	H22B···H11A	2.5027
C14···C11^iii	3.591 (3)	H22B···Cl2^x	3.0806
C14···N3^iii	3.400 (3)	H23B···C5^ix	3.0917
C15···C12^iii	3.580 (3)	H23B···C12	2.9947
C16···C12^iii	3.525 (3)	H23B···C13	3.0314
C16···C13^iii	3.567 (3)	H23B···N5^viii	2.8987
C17···C14^iii	3.554 (3)	H24A···N5^x	2.6327
C17···C13^iii	3.494 (3)	H24A···C21^x	3.0524
C21···C6^v	3.513 (3)	H24A···N5^viii	2.8214
C21···C13^viii	3.585 (3)	H24A···N4	2.9490
C24···N5^viii	3.405 (5)	H24B···Cl2^x	2.8678
C3···H18A	2.8900	H24B···H22B	2.4043
C5···H23B^ix	3.0917	H101···Cl2^i	2.3306
C6···H9A	2.9009	H102···Cl1	2.4520
C7···H10B	3.0205	H102···H8A	2.4939
C7···H9A	3.0312	H201···H18B^i	2.5026
C8···H6A	3.0286	H201···Cl1	2.1942
C9···H6A	3.0795	H201···H8A	2.4528
C9···H11A	2.6470	H202···Cl2	2.1059
H201—O1W—H202	104.58	C7—C6—H6A	121.96
H101—O2W—H102	110.73	N2—C8—H8B	109.02
C1—N1—C2	108.45 (17)	N2—C8—H8A	109.02
C2—N1—C18	125.72 (16)	H8A—C8—H8B	107.79
C1—N1—C18	125.71 (17)	C9—C8—H8A	109.03
C1—N2—C8	125.06 (16)	C9—C8—H8B	109.01
C7—N2—C8	126.78 (17)	C8—C9—H9A	109.21
C1—N2—C7	108.13 (16)	C10—C9—H9B	109.18
C11—N3—C17	108.14 (16)	C8—C9—H9B	109.19
C10—N3—C11	127.98 (16)	C10—C9—H9A	109.20
C10—N3—C17	123.77 (19)	H9A—C9—H9B	107.91
C12—N4—C22	126.18 (16)	C9—C10—H10A	109.15
C11—N4—C12	107.58 (18)	C9—C10—H10B	109.17
C11—N4—C22	126.05 (18)	N3—C10—H10B	109.17
N1—C1—N2	110.52 (17)	N3—C10—H10A	109.14
C3—C2—C7	122.05 (19)	H10A—C10—H10B	107.88
N1—C2—C3	131.7 (2)	N4—C11—H11A	124.54
N1—C2—C7	106.25 (16)	N3—C11—H11A	124.54
C2—C3—C4	116.1 (2)	C14—C13—H13A	122.00
C3—C4—C5	121.7 (2)	C12—C13—H13A	122.05
C4—C5—C6	122.3 (3)	C15—C14—H14A	118.94
C5—C6—C7	116.1 (2)	C13—C14—H14A	118.93
N2—C7—C6	131.51 (18)	C14—C15—H15A	119.04
N2—C7—C2	106.65 (17)	C16—C15—H15A	119.06
C2—C7—C6	121.81 (17)	C15—C16—H16A	121.93
N2—C8—C9	112.83 (15)	C17—C16—H16A	121.97
C8—C9—C10	112.06 (19)	C19—C18—H18A	109.14
N3—C10—C9	112.2 (2)	C19—C18—H18B	109.20
N3—C11—N4	110.91 (17)	H18A—C18—H18B	107.88
N4—C12—C17	106.53 (16)	N1—C18—H18B	109.11
N4—C12—C13	131.7 (2)	N1—C18—H18A	109.06
C13—C12—C17	121.7 (2)	C20—C19—H19A	110.17
C12—C13—C14	115.9 (2)	C18—C19—H19A	110.19
C13—C14—C15	122.1 (2)	C18—C19—H19B	110.25
C14—C15—C16	121.9 (3)	H19A—C19—H19B	108.49
C15—C16—C17	116.1 (2)	C20—C19—H19B	110.22
N3—C17—C16	130.97 (19)	C19—C20—H20B	108.79
C12—C17—C16	122.18 (18)	C19—C20—H20A	108.84
N3—C17—C12	106.83 (19)	H20A—C20—H20B	107.71
N1—C18—C19	112.35 (17)	C21—C20—H20A	108.90
C18—C19—C20	107.52 (17)	C21—C20—H20B	108.88
C19—C20—C21	113.57 (18)	C23—C22—H22A	108.62
N5—C21—C20	178.0 (3)	C23—C22—H22B	108.62
N4—C22—C23	114.46 (17)	H22A—C22—H22B	107.59
C22—C23—C24	113.54 (19)	N4—C22—H22A	108.68
C23—C24—C25	110.9 (2)	N4—C22—H22B	108.66
N6—C25—C24	178.7 (3)	C24—C23—H23A	108.81
N2—C1—H1A	124.75	C22—C23—H23A	108.87
N1—C1—H1A	124.74	C22—C23—H23B	108.90
C4—C3—H3A	121.92	H23A—C23—H23B	107.70
C2—C3—H3A	121.99	C24—C23—H23B	108.87
C3—C4—H4A	119.11	C23—C24—H24B	109.47
C5—C4—H4A	119.20	C23—C24—H24A	109.42
C6—C5—H5A	118.88	H24A—C24—H24B	108.04
C4—C5—H5A	118.86	C25—C24—H24A	109.45
C5—C6—H6A	121.96	C25—C24—H24B	109.46
C2—N1—C1—N2	0.2 (2)	C11—N4—C22—C23	−111.9 (2)
C18—N1—C1—N2	−175.88 (16)	C12—N4—C22—C23	73.8 (2)
C1—N1—C2—C3	−178.39 (19)	N1—C2—C3—C4	178.15 (18)
C1—N1—C2—C7	−0.79 (19)	C7—C2—C3—C4	0.9 (3)
C18—N1—C2—C3	−2.3 (3)	N1—C2—C7—N2	1.10 (18)
C18—N1—C2—C7	175.24 (16)	N1—C2—C7—C6	−177.03 (16)
C1—N1—C18—C19	−92.4 (2)	C3—C2—C7—C6	0.9 (3)
C2—N1—C18—C19	92.2 (2)	C3—C2—C7—N2	178.98 (16)
C7—N2—C1—N1	0.6 (2)	C2—C3—C4—C5	−1.3 (3)
C8—N2—C1—N1	178.67 (15)	C3—C4—C5—C6	0.1 (3)
C1—N2—C7—C2	−1.03 (18)	C4—C5—C6—C7	1.6 (3)
C1—N2—C7—C6	176.84 (18)	C5—C6—C7—C2	−2.0 (3)
C8—N2—C7—C2	−179.11 (15)	C5—C6—C7—N2	−179.64 (18)
C8—N2—C7—C6	−1.2 (3)	N2—C8—C9—C10	−52.0 (2)
C1—N2—C8—C9	118.3 (2)	C8—C9—C10—N3	−179.30 (18)
C7—N2—C8—C9	−63.9 (2)	N4—C12—C13—C14	178.2 (2)
C11—N3—C10—C9	8.3 (3)	C17—C12—C13—C14	1.3 (3)
C17—N3—C10—C9	−176.08 (18)	N4—C12—C17—N3	−1.0 (2)
C10—N3—C11—N4	176.1 (2)	N4—C12—C17—C16	−179.53 (18)
C17—N3—C11—N4	−0.1 (2)	C13—C12—C17—N3	176.65 (17)
C10—N3—C17—C12	−175.7 (2)	C13—C12—C17—C16	−1.9 (3)
C10—N3—C17—C16	2.7 (3)	C12—C13—C14—C15	0.0 (3)
C11—N3—C17—C12	0.7 (2)	C13—C14—C15—C16	−0.8 (3)
C11—N3—C17—C16	179.1 (2)	C14—C15—C16—C17	0.3 (3)
C12—N4—C11—N3	−0.5 (2)	C15—C16—C17—C12	1.1 (3)
C22—N4—C11—N3	−175.72 (17)	C15—C16—C17—N3	−177.14 (19)
C11—N4—C12—C13	−176.4 (2)	N1—C18—C19—C20	−176.83 (16)
C11—N4—C12—C17	0.9 (2)	C18—C19—C20—C21	−171.87 (17)
C22—N4—C12—C13	−1.2 (3)	N4—C22—C23—C24	72.7 (3)
C22—N4—C12—C17	176.10 (17)	C22—C23—C24—C25	170.5 (2)

Symmetry codes: (i) −x, −y+1, −z+1; (ii) x+1, y−1, z; (iii) −x+1, −y+1, −z; (iv) −x+1, −y+1, −z+1; (v) x−1, y, z; (vi) x, y−1, z; (vii) −x, −y+2, −z+1; (viii) −x, −y+2, −z; (ix) −x+1, −y+2, −z; (x) x+1, y, z; (xi) x−1, y+1, z; (xii) x, y+1, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2W—H101···Cl2^i	0.89	2.33	3.178 (2)	160
O2W—H102···Cl1	0.98	2.45	3.391 (2)	161
O1W—H201···Cl1	1.02	2.19	3.163 (2)	158
O1W—H202···Cl2	1.07	2.11	3.159 (2)	168
C1—H1A···O1W^i	0.93	2.44	3.121 (3)	130
C10—H10B···N2	0.97	2.57	2.912 (3)	101
C10—H10B···N6^ix	0.97	2.57	3.503 (4)	161
C11—H11A···O2W^iv	0.93	2.15	3.082 (3)	178
C14—H14A···Cl1^iii	0.93	2.83	3.740 (2)	166
C20—H20A···Cl1^i	0.97	2.71	3.666 (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.