N,N′-Bis(benzimidazol-1-ium-2-ylmeth­yl)-N,N′-bis­(benzimidazol-2-ylmeth­yl)cyclo­hexane-1,2-trans-diamine bis­(perchlorate) dihydrate

Li, J.; Meng, X.-G.; Liao, Z.-R.

doi:10.1107/S1600536805022865

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N,N′-Bis(benzimidazol-1-ium-2-ylmethyl)-N,N′-bis(benzimidazol-2-ylmethyl)cyclohexane-1,2-trans-diamine bis(perchlorate) dihydrate

J. Li, X.-G. Meng and Z.-R. Liao

In the cation of the title compound, C₃₈H₄₀N₁₀²⁺·2ClO₄⁻·2H₂O, the cyclohexanediamine group has a twofold axis and two of the four pendant benzimidazole groups are protonated. There are hydrogen bonds and π–π interactions in the crystal structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805022865/ob6538sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805022865/ob6538Isup2.hkl Contains datablock I

CCDC reference: 287672

checkCIF report

Key indicators

Single-crystal X-ray study
T = 292 K
Mean (C-C) = 0.004 Å
R factor = 0.059
wR factor = 0.174
Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        Cl1
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2
PLAT731_ALERT_1_C Bond    Calc     0.82(3), Rep   0.814(10) ......       3.00 su-Rat
              O1W  -H1WA    1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.82(3), Rep   0.821(10) ......       3.00 su-Rat
              O1W  -H1WB    1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.82(3), Rep   0.810(10) ......       3.00 su-Rat
              O1W  -H1#     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.82(3), Rep   0.820(10) ......       3.00 su-Rat
              O1W  -H2#     1.555   1.555

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

Histidine is an important ligand in iron, copper, zinc and manganese metalloproteins, such as superoxide dismutases, lipoxygenase, tyrosinase, amine oxidaes and hemocyanin (Que & Raymond, 1996; Kaim & Rall, 1996). N,N,N',N'-Tetrakis(2-benzimidazolymethyl)-1,2-trans-diaminocyclohexane (ctb) is a benzimidazole-rich ligand, which has an advantage thatthe basicity of the coordinating group approximates that of histidine (pK_b: histidine = 7.96 and benzimidazole = 8.47; Main, 1992)·We obtained the title compound, (I), H₂ctb²⁺·2ClO₄⁻·2H₂O, in the process of synthesizing a ctb–metal complex in 95% ethanol.

In (I), the H₂ctb²⁺ cation has a twofold axis (Fig. 1). All four benzimidazolyl groups are pushed in one side of cyclohexane ring, which is in a chair form similar to the ring in 1,2-cyclohexanediaminetetraacetic acid. The amine N atoms [N1 and N1ⁱ; symmetry code: (i) −x, y, 1/2 − z] over two positions adopt a trans conformation. There are intramolecular N—H···N hydrogen bonds (N5—H5···N2ⁱ and the symmetry-related bond), and also N—H···O and O—H···O intermolecular hydrogen bonds (Table 1) between H₂ctb²⁺ and H₂O or perchlorate, producing a three-dimensional framework (Fig. 2).

In the H₂ctb²⁺ cation, two five-membered rings, denoted A (atoms N2/C5/N3/C6/C11) and B (N4/C13/N5/C19/C14), are stacked 3.471 (2) Å apart, the dihedral angle between them being 18.88 (2)°. Furthermore, intermolecular π–π interactions exit between ring A and ring B at (x, 1 − y, z − 1/2), the distance between the centroids of the rings being 3.710 (2) Å and the dihedral angle 9.58 (2)° (Fig. 3).

Experimental top

All reagents and solvents were used as obtained without further purification. Compound (I) was synthesized by refluxing stoichiometric quantities (1:2 molar ratio) of ctb (0.32 g, 0.5 mmol) and ferric perchlorate (0.52 g, 1 mmol) in 95% ethanol (30 ml) at 333 K for 6 h. The solution was cooled to room temperature, filtered and evaporated to obtain the product (yield 42%). Crystals of (I) were grown from an ethanol solution by slow evaporation.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. The structure of (I), showing displacement ellipsoids drawn at the 30% probability level. [Symmetry code: (a) −x, y, 1/2 − z.]
	Fig. 2. The linking of the molecules via hydrogen bonds (dashed lines).
	Fig. 3. A view of the π–π stacking in the crystal structure. [Symmetry codes: (a) −x, y, 1/2 − z; (d) x, 1 − y, z − 1/2; (e) −x, y, −1/2 − z.]

N,N'-Bis(benzimidazol-1-ium-2-ylmethyl)-N,N'-bis(benzimidazol-2- ylmethyl)cyclohexane-1,2-trans-diamine bis(perchlorate) dihydrate top

Crystal data top

C₃₈H₄₀N₁₀²⁺·2ClO₄⁻·2H₂O	F(000) = 1824
M_r = 871.73	D_x = 1.440 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 5855 reflections
a = 16.4609 (10) Å	θ = 2.2–24.8°
b = 17.6108 (11) Å	µ = 0.23 mm⁻¹
c = 13.8677 (9) Å	T = 292 K
V = 4020.1 (4) Å³	Block, pink
Z = 4	0.40 × 0.30 × 0.22 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2954 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.028
Graphite monochromator	θ_max = 25.0°, θ_min = 1.7°
ϕ and ω scans	h = −19→14
19135 measured reflections	k = −20→20
3536 independent reflections	l = −16→16

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.174	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0915P)² + 3.4612P] where P = (F_o² + 2F_c²)/3
3536 reflections	(Δ/σ)_max < 0.001
291 parameters	Δρ_max = 0.51 e Å⁻³
6 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

C₃₈H₄₀N₁₀²⁺·2ClO₄⁻·2H₂O	V = 4020.1 (4) Å³
M_r = 871.73	Z = 4
Orthorhombic, Pbcn	Mo Kα radiation
a = 16.4609 (10) Å	µ = 0.23 mm⁻¹
b = 17.6108 (11) Å	T = 292 K
c = 13.8677 (9) Å	0.40 × 0.30 × 0.22 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2954 reflections with I > 2σ(I)
19135 measured reflections	R_int = 0.028
3536 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	6 restraints
wR(F²) = 0.174	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.51 e Å⁻³
3536 reflections	Δρ_min = −0.42 e Å⁻³
291 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.03650 (14)	0.25631 (13)	0.21638 (17)	0.0354 (5)
H1	0.0153	0.2496	0.1509	0.043*
C2	0.08795 (15)	0.18587 (14)	0.2388 (2)	0.0427 (6)
H2A	0.1360	0.1858	0.1982	0.051*
H2B	0.1055	0.1875	0.3055	0.051*
C3	0.03942 (17)	0.11360 (15)	0.2213 (2)	0.0515 (7)
H3A	0.0271	0.1092	0.1532	0.062*
H3B	0.0719	0.0700	0.2398	0.062*
C4	0.13608 (18)	0.33572 (15)	0.1371 (2)	0.0509 (7)
H4A	0.1114	0.3129	0.0805	0.061*
H4B	0.1845	0.3068	0.1524	0.061*
C5	0.16038 (16)	0.41537 (15)	0.11334 (19)	0.0421 (6)
C6	0.24379 (16)	0.50689 (16)	0.06967 (18)	0.0423 (6)
C7	0.30892 (18)	0.55253 (18)	0.0425 (2)	0.0521 (7)
H7	0.3609	0.5329	0.0345	0.063*
C8	0.2924 (2)	0.62778 (18)	0.0283 (2)	0.0574 (8)
H8	0.3342	0.6602	0.0101	0.069*
C9	0.2148 (2)	0.65712 (18)	0.0403 (2)	0.0592 (8)
H9	0.2061	0.7087	0.0303	0.071*
C10	0.15006 (19)	0.61162 (17)	0.0668 (2)	0.0547 (8)
H10	0.0981	0.6316	0.0740	0.066*
C11	0.16533 (15)	0.53446 (15)	0.08257 (18)	0.0405 (6)
C12	0.11660 (19)	0.34608 (15)	0.3107 (2)	0.0484 (7)
H12A	0.1695	0.3218	0.3138	0.058*
H12B	0.0831	0.3248	0.3615	0.058*
C13	0.12633 (15)	0.42946 (14)	0.32713 (18)	0.0398 (6)
C14	0.18533 (16)	0.54165 (14)	0.33873 (18)	0.0399 (6)
C15	0.23956 (18)	0.60150 (17)	0.3425 (2)	0.0557 (8)
H15	0.2954	0.5941	0.3394	0.067*
C16	0.2061 (2)	0.67243 (18)	0.3509 (3)	0.0720 (10)
H16	0.2404	0.7143	0.3543	0.086*
C17	0.1233 (2)	0.68364 (19)	0.3546 (3)	0.0750 (11)
H17	0.1034	0.7330	0.3585	0.090*
C18	0.0695 (2)	0.62450 (18)	0.3526 (3)	0.0627 (9)
H18	0.0137	0.6325	0.3558	0.075*
C19	0.10211 (16)	0.55184 (15)	0.34553 (19)	0.0416 (6)
Cl1	0.05493 (5)	0.16369 (5)	0.56061 (6)	0.0643 (3)
H3	0.2758 (13)	0.3975 (12)	0.087 (2)	0.042 (8)*
H4	0.2428 (11)	0.4414 (16)	0.319 (2)	0.054 (9)*
H5	0.0180 (8)	0.4676 (17)	0.348 (2)	0.056 (9)*
H1WA	0.370 (2)	0.388 (3)	0.2513 (17)	0.15 (2)*
H1WB	0.3836 (18)	0.403 (2)	0.3447 (18)	0.079 (12)*
N1	0.07940 (12)	0.32982 (11)	0.21747 (15)	0.0370 (5)
N2	0.11292 (13)	0.47540 (12)	0.11020 (16)	0.0426 (5)
N3	0.23839 (13)	0.43092 (13)	0.09033 (17)	0.0441 (5)
N4	0.19777 (13)	0.46437 (12)	0.32765 (16)	0.0396 (5)
N5	0.06760 (13)	0.48019 (13)	0.33955 (16)	0.0426 (5)
O1	0.0245 (3)	0.2303 (2)	0.5190 (3)	0.1407 (16)
O2	0.1068 (3)	0.1319 (3)	0.4944 (3)	0.178 (2)
O3	−0.0070 (3)	0.1168 (4)	0.5792 (5)	0.201 (3)
O4	0.1017 (4)	0.1796 (3)	0.6388 (4)	0.202 (3)
O1W	0.35008 (17)	0.4046 (2)	0.3009 (2)	0.1004 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0351 (12)	0.0336 (12)	0.0377 (12)	−0.0009 (10)	−0.0031 (10)	−0.0019 (10)
C2	0.0375 (13)	0.0383 (13)	0.0522 (15)	0.0057 (11)	0.0012 (12)	−0.0020 (11)
C3	0.0533 (16)	0.0330 (13)	0.0683 (19)	0.0076 (12)	−0.0047 (14)	−0.0049 (12)
C4	0.0479 (16)	0.0437 (15)	0.0610 (18)	0.0026 (12)	0.0161 (13)	0.0032 (13)
C5	0.0386 (14)	0.0456 (14)	0.0420 (14)	0.0001 (11)	0.0047 (11)	0.0034 (11)
C6	0.0397 (13)	0.0512 (15)	0.0360 (13)	−0.0034 (12)	0.0001 (11)	0.0028 (11)
C7	0.0419 (15)	0.0652 (19)	0.0493 (16)	−0.0106 (13)	0.0019 (12)	−0.0011 (13)
C8	0.0625 (19)	0.0580 (19)	0.0516 (17)	−0.0224 (15)	0.0065 (14)	−0.0021 (14)
C9	0.076 (2)	0.0463 (16)	0.0556 (18)	−0.0075 (15)	0.0126 (16)	0.0036 (13)
C10	0.0567 (18)	0.0499 (16)	0.0576 (18)	0.0048 (14)	0.0119 (14)	0.0080 (13)
C11	0.0397 (14)	0.0461 (14)	0.0356 (13)	−0.0038 (11)	0.0031 (10)	0.0026 (11)
C12	0.0547 (17)	0.0403 (14)	0.0503 (16)	−0.0078 (12)	−0.0126 (13)	0.0021 (12)
C13	0.0409 (14)	0.0404 (14)	0.0383 (13)	−0.0090 (11)	−0.0065 (11)	0.0007 (10)
C14	0.0383 (14)	0.0413 (14)	0.0402 (13)	−0.0056 (11)	0.0027 (10)	−0.0028 (11)
C15	0.0444 (16)	0.0513 (17)	0.071 (2)	−0.0133 (13)	0.0061 (14)	−0.0044 (14)
C16	0.072 (2)	0.0434 (17)	0.101 (3)	−0.0200 (16)	0.017 (2)	−0.0113 (17)
C17	0.086 (3)	0.0391 (17)	0.100 (3)	0.0010 (16)	0.027 (2)	−0.0061 (16)
C18	0.0511 (17)	0.0560 (19)	0.081 (2)	0.0096 (14)	0.0160 (16)	−0.0018 (16)
C19	0.0391 (14)	0.0422 (14)	0.0434 (14)	−0.0029 (11)	0.0041 (11)	−0.0015 (11)
Cl1	0.0484 (5)	0.0836 (6)	0.0608 (5)	0.0073 (4)	−0.0058 (3)	0.0076 (4)
N1	0.0364 (11)	0.0347 (11)	0.0399 (12)	−0.0039 (8)	0.0011 (9)	−0.0005 (8)
N2	0.0365 (11)	0.0446 (12)	0.0466 (13)	−0.0006 (9)	0.0039 (9)	0.0058 (10)
N3	0.0328 (11)	0.0480 (13)	0.0514 (13)	0.0034 (10)	0.0057 (10)	0.0056 (10)
N4	0.0331 (12)	0.0405 (12)	0.0451 (12)	−0.0004 (9)	−0.0024 (9)	−0.0032 (9)
N5	0.0308 (11)	0.0468 (13)	0.0502 (13)	−0.0080 (10)	−0.0011 (10)	0.0022 (10)
O1	0.183 (4)	0.139 (3)	0.100 (2)	0.076 (3)	−0.043 (2)	−0.001 (2)
O2	0.142 (3)	0.254 (6)	0.139 (4)	0.126 (4)	0.059 (3)	0.047 (3)
O3	0.117 (3)	0.238 (6)	0.248 (6)	−0.078 (4)	0.067 (4)	0.001 (5)
O4	0.311 (7)	0.160 (4)	0.134 (4)	−0.066 (4)	−0.140 (4)	0.049 (3)
O1W	0.0658 (17)	0.173 (3)	0.0624 (17)	0.0516 (19)	−0.0047 (14)	−0.0190 (19)

Geometric parameters (Å, º) top

C1—N1	1.475 (3)	C12—N1	1.459 (3)
C1—C1ⁱ	1.521 (5)	C12—C13	1.495 (4)
C1—C2	1.534 (3)	C12—H12A	0.9700
C1—H1	0.9800	C12—H12B	0.9700
C2—C3	1.522 (4)	C13—N4	1.327 (3)
C2—H2A	0.9700	C13—N5	1.327 (3)
C2—H2B	0.9700	C14—C15	1.382 (4)
C3—C3ⁱ	1.522 (6)	C14—C19	1.385 (4)
C3—H3A	0.9700	C14—N4	1.385 (3)
C3—H3B	0.9700	C15—C16	1.370 (5)
C4—N1	1.457 (3)	C15—H15	0.9300
C4—C5	1.495 (4)	C16—C17	1.378 (5)
C4—H4A	0.9700	C16—H16	0.9300
C4—H4B	0.9700	C17—C18	1.368 (5)
C5—N2	1.315 (3)	C17—H17	0.9300
C5—N3	1.351 (3)	C18—C19	1.391 (4)
C6—N3	1.371 (4)	C18—H18	0.9300
C6—C11	1.391 (4)	C19—N5	1.386 (3)
C6—C7	1.392 (4)	Cl1—O3	1.337 (4)
C7—C8	1.367 (4)	Cl1—O4	1.358 (4)
C7—H7	0.9300	Cl1—O2	1.373 (4)
C8—C9	1.387 (5)	Cl1—O1	1.400 (3)
C8—H8	0.9300	N3—H3	0.853 (10)
C9—C10	1.383 (4)	N4—H4	0.852 (10)
C9—H9	0.9300	N5—H5	0.853 (10)
C10—C11	1.399 (4)	O1W—H1WA	0.814 (10)
C10—H10	0.9300	O1W—H1WB	0.821 (10)
C11—N2	1.405 (3)

N1—C1—C1ⁱ	111.84 (14)	N1—C12—H12A	109.2
N1—C1—C2	116.33 (19)	C13—C12—H12A	109.2
C1ⁱ—C1—C2	108.17 (17)	N1—C12—H12B	109.2
N1—C1—H1	106.6	C13—C12—H12B	109.2
C1ⁱ—C1—H1	106.6	H12A—C12—H12B	107.9
C2—C1—H1	106.6	N4—C13—N5	109.4 (2)
C3—C2—C1	110.8 (2)	N4—C13—C12	123.4 (2)
C3—C2—H2A	109.5	N5—C13—C12	127.1 (2)
C1—C2—H2A	109.5	C15—C14—C19	122.5 (3)
C3—C2—H2B	109.5	C15—C14—N4	131.1 (3)
C1—C2—H2B	109.5	C19—C14—N4	106.3 (2)
H2A—C2—H2B	108.1	C16—C15—C14	116.0 (3)
C3ⁱ—C3—C2	111.37 (19)	C16—C15—H15	122.0
C3ⁱ—C3—H3A	109.4	C14—C15—H15	122.0
C2—C3—H3A	109.4	C15—C16—C17	122.1 (3)
C3ⁱ—C3—H3B	109.4	C15—C16—H16	119.0
C2—C3—H3B	109.4	C17—C16—H16	119.0
H3A—C3—H3B	108.0	C18—C17—C16	122.1 (3)
N1—C4—C5	114.0 (2)	C18—C17—H17	119.0
N1—C4—H4A	108.8	C16—C17—H17	119.0
C5—C4—H4A	108.8	C17—C18—C19	116.8 (3)
N1—C4—H4B	108.8	C17—C18—H18	121.6
C5—C4—H4B	108.8	C19—C18—H18	121.6
H4A—C4—H4B	107.6	C14—C19—N5	106.5 (2)
N2—C5—N3	113.2 (2)	C14—C19—C18	120.4 (3)
N2—C5—C4	127.0 (2)	N5—C19—C18	133.1 (3)
N3—C5—C4	119.8 (2)	O3—Cl1—O4	113.9 (4)
N3—C6—C11	104.7 (2)	O3—Cl1—O2	110.5 (4)
N3—C6—C7	132.1 (3)	O4—Cl1—O2	105.4 (4)
C11—C6—C7	123.3 (3)	O3—Cl1—O1	108.9 (4)
C8—C7—C6	116.4 (3)	O4—Cl1—O1	111.0 (3)
C8—C7—H7	121.8	O2—Cl1—O1	106.8 (3)
C6—C7—H7	121.8	C4—N1—C12	113.3 (2)
C7—C8—C9	121.8 (3)	C4—N1—C1	111.18 (19)
C7—C8—H8	119.1	C12—N1—C1	112.48 (19)
C9—C8—H8	119.1	C5—N2—C11	103.9 (2)
C10—C9—C8	121.7 (3)	C5—N3—C6	108.0 (2)
C10—C9—H9	119.2	C5—N3—H3	124.1 (19)
C8—C9—H9	119.2	C6—N3—H3	127.8 (19)
C9—C10—C11	117.7 (3)	C13—N4—C14	108.9 (2)
C9—C10—H10	121.1	C13—N4—H4	123 (2)
C11—C10—H10	121.1	C14—N4—H4	128 (2)
C6—C11—C10	119.1 (2)	C13—N5—C19	108.8 (2)
C6—C11—N2	110.3 (2)	C13—N5—H5	123 (2)
C10—C11—N2	130.7 (3)	C19—N5—H5	128 (2)
N1—C12—C13	111.9 (2)	H1WA—O1W—H1WB	109.9 (18)

N1—C1—C2—C3	−171.9 (2)	C17—C18—C19—C14	−1.4 (5)
C1ⁱ—C1—C2—C3	61.2 (3)	C17—C18—C19—N5	−178.3 (3)
C1—C2—C3—C3ⁱ	−55.4 (4)	C5—C4—N1—C12	−71.8 (3)
N1—C4—C5—N2	−41.9 (4)	C5—C4—N1—C1	160.4 (2)
N1—C4—C5—N3	139.4 (3)	C13—C12—N1—C4	78.5 (3)
N3—C6—C7—C8	−179.4 (3)	C13—C12—N1—C1	−154.3 (2)
C11—C6—C7—C8	−0.2 (4)	C1ⁱ—C1—N1—C4	−166.1 (2)
C6—C7—C8—C9	0.0 (4)	C2—C1—N1—C4	68.9 (3)
C7—C8—C9—C10	−0.4 (5)	C1ⁱ—C1—N1—C12	65.6 (3)
C8—C9—C10—C11	0.8 (5)	C2—C1—N1—C12	−59.3 (3)
N3—C6—C11—C10	−180.0 (2)	N3—C5—N2—C11	0.1 (3)
C7—C6—C11—C10	0.7 (4)	C4—C5—N2—C11	−178.7 (3)
N3—C6—C11—N2	−0.4 (3)	C6—C11—N2—C5	0.2 (3)
C7—C6—C11—N2	−179.7 (2)	C10—C11—N2—C5	179.7 (3)
C9—C10—C11—C6	−0.9 (4)	N2—C5—N3—C6	−0.4 (3)
C9—C10—C11—N2	179.6 (3)	C4—C5—N3—C6	178.6 (2)
N1—C12—C13—N4	−109.8 (3)	C11—C6—N3—C5	0.4 (3)
N1—C12—C13—N5	67.5 (4)	C7—C6—N3—C5	179.7 (3)
C19—C14—C15—C16	−1.6 (4)	N5—C13—N4—C14	−1.4 (3)
N4—C14—C15—C16	177.8 (3)	C12—C13—N4—C14	176.3 (2)
C14—C15—C16—C17	−0.6 (6)	C15—C14—N4—C13	−179.1 (3)
C15—C16—C17—C18	1.8 (6)	C19—C14—N4—C13	0.3 (3)
C16—C17—C18—C19	−0.8 (6)	N4—C13—N5—C19	1.9 (3)
C15—C14—C19—N5	−179.7 (3)	C12—C13—N5—C19	−175.7 (2)
N4—C14—C19—N5	0.8 (3)	C14—C19—N5—C13	−1.6 (3)
C15—C14—C19—C18	2.6 (4)	C18—C19—N5—C13	175.6 (3)
N4—C14—C19—C18	−176.9 (3)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···N2ⁱ	0.85 (1)	2.24 (2)	3.053 (3)	160 (3)
N3—H3···O2ⁱⁱ	0.85 (1)	2.38 (2)	3.081 (5)	140 (2)
N3—H3···O4ⁱⁱ	0.85 (1)	2.54 (2)	3.342 (8)	158 (3)
N4—H4···O1W	0.85 (1)	1.90 (1)	2.744 (3)	172 (3)
O1W—H1WA···O4ⁱⁱ	0.81 (1)	2.02 (2)	2.808 (5)	162 (6)
O1W—H1WB···O3ⁱⁱⁱ	0.82 (1)	2.12 (2)	2.904 (5)	161 (3)
C1—H1···O1ⁱ	0.98	2.47	3.446 (4)	175

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

Experimental details

Crystal data
Chemical formula	C₃₈H₄₀N₁₀²⁺·2ClO₄⁻·2H₂O
M_r	871.73
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	292
a, b, c (Å)	16.4609 (10), 17.6108 (11), 13.8677 (9)
V (Å³)	4020.1 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.40 × 0.30 × 0.22

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	19135, 3536, 2954
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.174, 1.04
No. of reflections	3536
No. of parameters	291
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.42

Computer programs: SMART (Bruker, 2000), SMART, SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···N2ⁱ	0.85 (1)	2.238 (15)	3.053 (3)	160 (3)
N3—H3···O2ⁱⁱ	0.85 (1)	2.38 (2)	3.081 (5)	140 (2)
N3—H3···O4ⁱⁱ	0.85 (1)	2.536 (17)	3.342 (8)	158 (3)
N4—H4···O1W	0.85 (1)	1.899 (11)	2.744 (3)	172 (3)
O1W—H1WA···O4ⁱⁱ	0.81 (1)	2.02 (2)	2.808 (5)	162 (6)
O1W—H1WB···O3ⁱⁱⁱ	0.82 (1)	2.116 (17)	2.904 (5)	161 (3)
C1—H1···O1ⁱ	0.98	2.47	3.446 (4)	175

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

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