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The title compound is an ethanol-solvated salt, C16H38N42+·2C11H7O2-·2C2H6O, in which the cation lies across a centre of inversion in P21/c. The ions are linked by N-H...O hydrogen bonds [H...O = 1.70 and 2.30 Å, N...O = 2.624 (2) and 3.136 (2) Å, and N-H...O = 178 and 151°], and the ethanol mol­ecule is linked to the anion by an O-H...O hydrogen bond [H...O = 1.90 Å, O...O = 2.728 (2) Å and O-H...O = 171°], to form a centrosymmetric five-component aggregate. C-H...O hydrogen bonds and aromatic [pi]-[pi]-stacking interactions are absent, but the aggregates are linked into sheets by a single C-H...[pi](arene) hydrogen bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270103002804/sk1618sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270103002804/sk1618Isup2.hkl
Contains datablock I

CCDC reference: 208026

Comment top

The nickel(II) complex [(RCOO)2Ni(cyclam)], where RCOO represents 2-naphthoate, C10H7COO, and cyclam is 1,4,8,11-tetraazacyclotetradecane, C10H24N4, is centrosymmetric, with naphthoate ligands occupying mutually trans sites in an octahedral NiN4O2 chromophore (Zakaria et al., 2002). An unexpected feature of this structure is the complete absence of aromatic π···π stacking interactions between the naphthalene rings in adjacent complexes, even though the closest approach between these rings is across a centre of inversion, so that the rings involved are strictly parallel. While the shortest interplanar spacing between such rings is only 3.122 (2) Å, the corresponding distance between the ring centroids is 5.260 (2) Å, with a corresponding centroid offset of 4.233 (2) Å, so that there is no ring overlap whatsoever.

Intrigued by this feature, we have now studied a related 2-naphthoic acid derivative, the title ethanol-solvated adduct, (I), formed between this acid and tet-a (meso-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane), C16H36N4. The constitution of (I) (Fig. 1) is that of a salt, C16H38N42+·2C10H7COO·2C2H5OH, in which the fully ordered cation lies across a centre of inversion, chosen for the sake of convenience as that at (1/2, 1/2, 1/2), while the anion and the ethanol molecule lie in general positions. \sch

The cation adopts the usual and characteristic trans-III configuration (Barefield et al., 1986), with four methyl groups in equatorial sites and two in axial sites, and with paired intra-cation N—H···N hydrogen bonds generating an R22(10) motif (Bernstein et al., 1995). There is almost perfect staggering about all of the C—C and C—N bonds in the cation (Table 1), and there are four axial N—H bonds available for intermolecular hydrogen-bond formation, two on each face of the disk-like cation. The C—N bond lengths in the cation (Table 1) are consistent with the site of N-protonation, while the C—C distances in the anion exhibit the marked bond fixation typical of the naphthalene ring system.

Within the selected asymmetric unit, atoms N1 at (x, y, z) and N4 at (1 − x, 1 − y, 1 − z), both part of the cation centred at (1/2, 1/2, 1/2), act as hydrogen-bond donors to, respectively, carboxylate atoms O1 and O2 in the anion at (x, y, z), forming an R33(8) motif, while ethanol atom O3 also acts as a donor towards O2 (Fig. 1). In this manner, a centrosymmetric five-component aggregate is formed, which accommodates all of the hard (Desiraju & Steiner, 1999) hydrogen-bond donors. Similar R33(8) motifs involving [(tet-a)H2]2+ cations and aromatic carboxylate anions have been observed in salts with terephthalate (Lough et al., 2000), 5-hydroxyisophthalate (Burchell et al., 2000) and 5-nitroisophthalate (MacLean et al., 2002), although not in the analogous salts formed by 3- and 4-hydroxybenzoate or 3,5-dihydroxybenzoate anions (Gregson et al., 2000).

For the closest approach of naphthalene rings in adjacent aggregates in (I), the centroid separation is 5.493 (2) Å. Whereas in [(C10H7COO)2Ni(cyclam)], the nearest-neighbour naphthoate units are related by inversion, in (I) they are related by a twofold screw axis, and the naphthalene rings involved are almost orthogonal (Fig. 2), with a dihedral angle of 84.5 (3)° between the ring planes, so that aromatic π···π stacking interactions are absent. However, the aggregates are linked into sheets by a single C—H···π(arene) hydrogen bond (Table 2). The metrical systematics of C—H···π(arene) hydrogen bonds have been studied by Braga et al. (1998) using neutron diffraction results extracted from the Cambridge Structural Database (CSD, Version?; Allen, 2002). The most frequently observed H···Cg distances (Cg represents the centroid of the arene ring) lie in the range 2.9–3.0 Å, while the mean values of the C—H ···Cg angle and the C···Cg distances were found to be 142 (2)° and 3.69 (2) Å, respectively. The values found here for (I) are thus fairly typical for interactions of this type.

Atom C7 in the cation is adjacent to a protonated ring N atom, and hence the axial C7—H7 bond can be expected to be moderately acidic for an aliphatic C—H bond. Atom C7 at (x, y, z), which lies in the cation centred at (1/2, 1/2, 1/2) acts as hydrogen-bond donor to the unsubstituted C15—C110 aryl ring of the anion at (x, 3/2 − y, z − 1/2), which forms part of the aggregate centred at (1/2, 1, 0), while atom C7 at (1 − x, 1 − y, 1 − z) in the same (1/2, 1/2, 1/2) aggregate acts as a donor to the naphthoate anion at (1 − x, y − 1/2, 3/2 − z), which is part of the aggregate centred at (1/2, 0, 1). The two naphthoate anions in the (1/2, 1/2, 1/2) aggregate likewise act as acceptors from atoms C7 in the aggregates centred at (1/2, 0, 0) and (1/2, 1, 1) and in this manner the five-component aggregates are linked into a (100) sheet (Fig. 3).

Table 2. Hydrogen-bond parameters (Å, °) for (I). Cg is the centroid of the C15—C110 ring in the anion.

Experimental top

Equimolar quantities of tet-a (Hay et al., 1975) and 2-naphthoic acid were separately dissolved in ethanol. The solutions were mixed and the mixture was set aside to crystallize, producing analytically pure (I). Analysis, found: C 69.9, H 8.9, N 8.1%; C42H64N4O6 requires: C 70.0, H 9.0, N 7.8%. Crystals of (I) suitable for single-crystal X-ray diffraction were selected directly from the analytical sample.

Refinement top

The space group P21/c was uniquely assigned from the systematic absences. H atoms were treated as riding, with O—H distances of 0.84 Å, N—H distances of 0.92 Å, and C—H distances of 0.95 (aromatic), 0.98 (CH3), 0.99 (CH2) or 1.00 Å (aliphatic CH).

Computing details top

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2002); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

Figures top
[Figure 1] Fig. 1. The centrosymmetric five-component aggregate in (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and, for the sake of clarity, H atoms bonded to C atoms have been omitted. The atoms marked with an asterisk (*) are at the symmetry position (1 − x, 1 − y, 1 − z).
[Figure 2] Fig. 2. A stereoview of part of the crystal structure of (I), showing the near orthogonality of adjacent naphthalene rings. For the sake of clarity, the ethanol molecules and H atoms bonded to C atoms have been omitted.
[Figure 3] Fig. 3. Part of the crystal structure of (I), showing the linking of the five-component aggregates into a (100) sheet by means of a C—H···π(arene) hydrogen bond. For the sake of clarity, the ethanol molecules and H atoms bonded to C atoms in the anion have been omitted. The atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (1 − x, 1 − y, 1 − z) and (x, 3/2 − y, z − 1/2), respectively.
Meso-5,5,7,12,12,14-hexamethyl-1,4-diaza-8,11-diazoniumcyclotetradecane bis(2-naphthoate) ethanol disolvate top
Crystal data top
C16H38N42+·2C11H7O2·2C2H6OF(000) = 784
Mr = 720.97Dx = 1.185 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4606 reflections
a = 10.9563 (4) Åθ = 2.8–27.5°
b = 10.9584 (5) ŵ = 0.08 mm1
c = 17.1665 (8) ÅT = 150 K
β = 101.446 (2)°Block, colourless
V = 2020.08 (15) Å30.32 × 0.25 × 0.20 mm
Z = 2
Data collection top
Nonius KappaCCD
diffractometer
3130 reflections with I > 2σ(I)
Radiation source: fine-focus sealed X-ray tubeRint = 0.075
Graphite monochromatorθmax = 27.5°, θmin = 2.8°
ϕ scans, and ω scans with κ offsetsh = 1413
17192 measured reflectionsk = 1414
4606 independent reflectionsl = 2222
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H-atom parameters constrained
wR(F2) = 0.130 w = 1/[σ2(Fo2) + (0.0539P)2 + 0.3194P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
4606 reflectionsΔρmax = 0.16 e Å3
241 parametersΔρmin = 0.17 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.014 (3)
Crystal data top
C16H38N42+·2C11H7O2·2C2H6OV = 2020.08 (15) Å3
Mr = 720.97Z = 2
Monoclinic, P21/cMo Kα radiation
a = 10.9563 (4) ŵ = 0.08 mm1
b = 10.9584 (5) ÅT = 150 K
c = 17.1665 (8) Å0.32 × 0.25 × 0.20 mm
β = 101.446 (2)°
Data collection top
Nonius KappaCCD
diffractometer
3130 reflections with I > 2σ(I)
17192 measured reflectionsRint = 0.075
4606 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.130H-atom parameters constrained
S = 1.02Δρmax = 0.16 e Å3
4606 reflectionsΔρmin = 0.17 e Å3
241 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.59018 (11)0.52392 (11)0.61507 (7)0.0312 (3)
C20.57058 (15)0.39781 (14)0.64207 (9)0.0356 (4)
C30.43695 (15)0.35860 (15)0.61481 (9)0.0370 (4)
N40.40393 (11)0.35695 (11)0.52786 (7)0.0325 (3)
C50.27070 (14)0.33163 (15)0.49161 (9)0.0361 (4)
C510.22189 (17)0.21533 (17)0.52546 (11)0.0480 (4)
C520.19147 (15)0.44189 (17)0.50605 (10)0.0439 (4)
C60.26297 (15)0.31186 (15)0.40202 (9)0.0368 (4)
C70.28454 (14)0.42168 (15)0.35181 (9)0.0348 (4)
C710.27610 (16)0.38570 (16)0.26513 (9)0.0429 (4)
O10.41503 (11)0.66378 (11)0.65109 (7)0.0457 (3)
O20.37126 (11)0.75854 (11)0.53397 (7)0.0440 (3)
C110.21341 (14)0.76163 (13)0.70018 (9)0.0320 (3)
C120.23857 (13)0.79095 (13)0.62741 (9)0.0310 (3)
C130.16199 (14)0.87711 (15)0.57892 (9)0.0365 (4)
C140.06376 (14)0.93073 (15)0.60461 (9)0.0385 (4)
C150.06156 (15)0.95855 (16)0.70949 (11)0.0430 (4)
C160.07952 (16)0.93351 (17)0.78424 (11)0.0466 (4)
C170.00250 (16)0.84944 (16)0.83312 (10)0.0432 (4)
C180.09168 (15)0.79137 (15)0.80623 (10)0.0376 (4)
C190.11366 (13)0.81656 (13)0.72887 (9)0.0319 (3)
C1100.03700 (14)0.90262 (14)0.68001 (9)0.0348 (4)
C1110.34968 (14)0.73366 (14)0.60124 (9)0.0340 (3)
O30.32676 (12)0.89822 (12)0.39975 (7)0.0528 (3)
C310.43030 (16)0.97600 (16)0.39884 (10)0.0444 (4)
C320.42512 (18)1.02307 (18)0.31655 (10)0.0500 (5)
H1A0.53000.57360.62870.037*
H1B0.57880.52370.56050.037*
H2A0.59280.39420.70080.043*
H2B0.62580.34090.62060.043*
H3A0.42520.27620.63570.044*
H3B0.38150.41570.63590.044*
H40.45220.29890.50970.039*
H51A0.27110.14500.51460.072*
H51B0.13440.20280.50040.072*
H51C0.22910.22420.58300.072*
H52A0.18880.44690.56270.066*
H52B0.10670.43240.47500.066*
H52C0.22840.51670.48970.066*
H6A0.32460.24840.39560.044*
H6B0.17950.27840.37950.044*
H70.21910.48420.35470.042*
H71A0.28760.45820.23400.064*
H71B0.19410.34990.24430.064*
H71C0.34110.32580.26140.064*
H110.26410.70300.73230.038*
H130.17880.89790.52830.044*
H140.01280.98770.57120.046*
H150.11561.01400.67680.052*
H160.14470.97320.80350.056*
H170.01600.83290.88510.052*
H180.14260.73400.83930.045*
H30.33680.86160.44350.079*
H31A0.50870.93020.41680.053*
H31B0.42881.04520.43570.053*
H32A0.34631.06620.29840.075*
H32B0.43110.95460.28080.075*
H32C0.49471.07930.31660.075*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0325 (7)0.0346 (7)0.0276 (6)0.0034 (5)0.0087 (5)0.0004 (5)
C20.0434 (9)0.0331 (8)0.0308 (8)0.0040 (7)0.0085 (6)0.0039 (6)
C30.0445 (9)0.0376 (9)0.0317 (8)0.0017 (7)0.0141 (7)0.0026 (7)
N40.0341 (7)0.0344 (7)0.0311 (6)0.0002 (5)0.0119 (5)0.0018 (5)
C50.0334 (8)0.0382 (9)0.0390 (9)0.0030 (6)0.0127 (7)0.0007 (7)
C510.0469 (10)0.0466 (10)0.0527 (11)0.0106 (8)0.0152 (8)0.0039 (8)
C520.0399 (9)0.0511 (10)0.0443 (9)0.0053 (8)0.0169 (7)0.0001 (8)
C60.0357 (8)0.0360 (8)0.0385 (9)0.0010 (6)0.0070 (7)0.0031 (7)
C70.0314 (8)0.0383 (9)0.0343 (8)0.0030 (6)0.0059 (6)0.0020 (7)
C710.0463 (10)0.0466 (10)0.0340 (8)0.0035 (8)0.0036 (7)0.0038 (7)
O10.0469 (7)0.0525 (7)0.0414 (6)0.0206 (6)0.0177 (5)0.0117 (6)
O20.0492 (7)0.0488 (7)0.0388 (6)0.0102 (5)0.0207 (5)0.0083 (5)
C110.0318 (8)0.0282 (7)0.0360 (8)0.0019 (6)0.0069 (6)0.0010 (6)
C120.0305 (8)0.0294 (8)0.0336 (8)0.0004 (6)0.0074 (6)0.0015 (6)
C130.0391 (9)0.0384 (9)0.0324 (8)0.0031 (7)0.0079 (7)0.0017 (7)
C140.0370 (8)0.0384 (9)0.0389 (9)0.0072 (7)0.0047 (7)0.0039 (7)
C150.0368 (9)0.0424 (9)0.0507 (10)0.0091 (7)0.0106 (7)0.0021 (8)
C160.0395 (9)0.0513 (10)0.0539 (11)0.0066 (8)0.0206 (8)0.0022 (9)
C170.0424 (9)0.0467 (10)0.0446 (9)0.0014 (8)0.0187 (8)0.0007 (8)
C180.0373 (8)0.0374 (9)0.0397 (9)0.0010 (7)0.0117 (7)0.0028 (7)
C190.0294 (7)0.0299 (7)0.0373 (8)0.0020 (6)0.0086 (6)0.0010 (6)
C1100.0311 (8)0.0339 (8)0.0398 (8)0.0004 (6)0.0079 (6)0.0029 (7)
C1110.0351 (8)0.0317 (8)0.0366 (8)0.0012 (6)0.0103 (7)0.0016 (7)
O30.0558 (8)0.0567 (8)0.0439 (7)0.0062 (6)0.0052 (6)0.0125 (6)
C310.0484 (10)0.0435 (10)0.0400 (9)0.0004 (8)0.0058 (7)0.0043 (8)
C320.0579 (11)0.0538 (11)0.0409 (9)0.0116 (9)0.0165 (8)0.0085 (8)
Geometric parameters (Å, º) top
N1—C21.487 (2)O1—C1111.2602 (19)
N1—C7i1.501 (2)O2—C1111.2538 (18)
N1—H1A0.92C11—C121.370 (2)
N1—H1B0.92C11—C191.419 (2)
C2—C31.508 (2)C11—H110.95
C2—H2A0.99C12—C131.418 (2)
C2—H2B0.99C12—C1111.515 (2)
N4—C31.465 (2)C13—C141.373 (2)
C3—H3A0.99C13—H130.95
C3—H3B0.99C14—C1101.417 (2)
N4—C51.495 (2)C14—H140.95
N4—H40.92C15—C161.364 (2)
C5—C521.536 (2)C15—C1101.419 (2)
C5—C61.539 (2)C15—H150.95
C5—C511.540 (2)C16—C171.409 (2)
C51—H51A0.98C16—H160.95
C51—H51B0.98C17—C181.368 (2)
C51—H51C0.98C17—H170.95
C52—H52A0.98C18—C191.423 (2)
C52—H52B0.98C18—H180.95
C52—H52C0.98C19—C1101.421 (2)
C6—C71.526 (2)O3—C311.421 (2)
C6—H6A0.99O3—H30.84
C6—H6B0.99C31—C321.494 (2)
C7—C711.524 (2)C31—H31A0.99
C7—H71.00C31—H31B0.99
C71—H71A0.98C32—H32A0.98
C71—H71B0.98C32—H32B0.98
C71—H71C0.98C32—H32C0.98
C2—N1—C7i115.40 (12)C7—C71—H71B109.5
C2—N1—H1A108.4H71A—C71—H71B109.5
C7i—N1—H1A108.4C7—C71—H71C109.5
C2—N1—H1B108.4H71A—C71—H71C109.5
C7i—N1—H1B108.4H71B—C71—H71C109.5
H1A—N1—H1B107.5C12—C11—C19121.69 (14)
N1—C2—C3111.07 (13)C12—C11—H11119.2
N1—C2—H2A109.4C19—C11—H11119.2
C3—C2—H2A109.4C11—C12—C13119.26 (13)
N1—C2—H2B109.4C11—C12—C111119.48 (13)
C3—C2—H2B109.4C13—C12—C111121.23 (13)
H2A—C2—H2B108.0C14—C13—C12120.43 (14)
N4—C3—C2110.36 (12)C14—C13—H13119.8
N4—C3—H3A109.6C12—C13—H13119.8
C2—C3—H3A109.6C13—C14—C110121.18 (15)
N4—C3—H3B109.6C13—C14—H14119.4
C2—C3—H3B109.6C110—C14—H14119.4
H3A—C3—H3B108.1C16—C15—C110120.70 (16)
C3—N4—C5116.74 (11)C16—C15—H15119.7
C3—N4—H4108.1C110—C15—H15119.7
C5—N4—H4108.1C15—C16—C17120.71 (15)
N4—C5—C52108.86 (13)C15—C16—H16119.6
N4—C5—C6107.32 (12)C17—C16—H16119.6
C52—C5—C6110.56 (13)C18—C17—C16120.40 (16)
N4—C5—C51112.34 (13)C18—C17—H17119.8
C52—C5—C51109.90 (13)C16—C17—H17119.8
C6—C5—C51107.84 (13)C17—C18—C19120.22 (15)
C5—C51—H51A109.5C17—C18—H18119.9
C5—C51—H51B109.5C19—C18—H18119.9
H51A—C51—H51B109.5C11—C19—C110118.85 (14)
C5—C51—H51C109.5C11—C19—C18121.76 (14)
H51A—C51—H51C109.5C110—C19—C18119.34 (14)
H51B—C51—H51C109.5C14—C110—C15122.81 (15)
C5—C52—H52A109.5C14—C110—C19118.59 (13)
C5—C52—H52B109.5C15—C110—C19118.59 (14)
H52A—C52—H52B109.5O2—C111—O1124.89 (14)
C5—C52—H52C109.5O2—C111—C12119.51 (14)
H52A—C52—H52C109.5O1—C111—C12115.60 (13)
H52B—C52—H52C109.5C31—O3—H3109.5
C7—C6—C5118.01 (13)O3—C31—C32109.68 (14)
C7—C6—H6A107.8O3—C31—H31A109.7
C5—C6—H6A107.8C32—C31—H31A109.7
C7—C6—H6B107.8O3—C31—H31B109.7
C5—C6—H6B107.8C32—C31—H31B109.7
H6A—C6—H6B107.1H31A—C31—H31B108.2
N1i—C7—C71110.27 (12)C31—C32—H32A109.5
N1i—C7—C6109.38 (12)C31—C32—H32B109.5
C71—C7—C6111.17 (13)H32A—C32—H32B109.5
N1i—C7—H7108.7C31—C32—H32C109.5
C71—C7—H7108.7H32A—C32—H32C109.5
C6—C7—H7108.7H32B—C32—H32C109.5
C7—C71—H71A109.5
N1—C2—C3—N462.09 (16)C15—C16—C17—C180.1 (3)
C2—C3—N4—C5174.22 (13)C16—C17—C18—C190.8 (3)
C3—N4—C5—C6170.12 (13)C12—C11—C19—C1101.1 (2)
N4—C5—C6—C769.22 (17)C12—C11—C19—C18176.40 (14)
C5—C6—C7—N1i56.87 (17)C17—C18—C19—C11177.53 (15)
C6—C7—N1i—C2i163.05 (12)C17—C18—C19—C1100.1 (2)
C7i—N1—C2—C3172.03 (12)C13—C14—C110—C15178.26 (16)
C3—N4—C5—C5270.19 (16)C13—C14—C110—C190.4 (2)
C3—N4—C5—C5151.76 (18)C16—C15—C110—C14176.37 (16)
C52—C5—C6—C749.37 (18)C16—C15—C110—C192.3 (3)
C51—C5—C6—C7169.54 (14)C11—C19—C110—C140.4 (2)
C5—C6—C7—C71178.87 (13)C18—C19—C110—C14177.16 (14)
C19—C11—C12—C130.9 (2)C11—C19—C110—C15179.13 (14)
C19—C11—C12—C111177.33 (14)C18—C19—C110—C151.6 (2)
C11—C12—C13—C140.1 (2)C11—C12—C111—O2178.54 (14)
C111—C12—C13—C14178.13 (15)C13—C12—C111—O23.3 (2)
C12—C13—C14—C1100.6 (2)C11—C12—C111—O12.1 (2)
C110—C15—C16—C171.5 (3)C13—C12—C111—O1176.06 (14)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···N4i0.922.042.791 (2)138
N1—H1A···O10.921.702.624 (2)178
N4—H4···O2i0.922.303.136 (2)151
O3—H3···O20.841.902.728 (2)171
C7—H7···Cg2ii1.002.943.785 (2)143
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+3/2, z1/2.

Experimental details

Crystal data
Chemical formulaC16H38N42+·2C11H7O2·2C2H6O
Mr720.97
Crystal system, space groupMonoclinic, P21/c
Temperature (K)150
a, b, c (Å)10.9563 (4), 10.9584 (5), 17.1665 (8)
β (°) 101.446 (2)
V3)2020.08 (15)
Z2
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.32 × 0.25 × 0.20
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
17192, 4606, 3130
Rint0.075
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.130, 1.02
No. of reflections4606
No. of parameters241
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.16, 0.17

Computer programs: KappaCCD Server Software (Nonius, 1997), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2002), SHELXL97 and PRPKAPPA (Ferguson, 1999).

Selected geometric parameters (Å, º) top
N1—C21.487 (2)N4—C31.465 (2)
N1—C7i1.501 (2)N4—C51.495 (2)
N1—C2—C3—N462.09 (16)C5—C6—C7—N1i56.87 (17)
C2—C3—N4—C5174.22 (13)C6—C7—N1i—C2i163.05 (12)
C3—N4—C5—C6170.12 (13)C7i—N1—C2—C3172.03 (12)
N4—C5—C6—C769.22 (17)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···N4i0.922.042.791 (2)138
N1—H1A···O10.921.702.624 (2)178
N4—H4···O2i0.922.303.136 (2)151
O3—H3···O20.841.902.728 (2)171
C7—H7···Cg2ii1.002.943.785 (2)143
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+3/2, z1/2.
 

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