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There are three independent mol­ecules in the asymmetric unit of the title compound, C15H25N6+·ClO4. The cations are linked to form an R_4^4(30) ring with two arms and are then linked into columns in the [010] direction by C(11) chains formed via C—H...N hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010300948X/de1210sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827010300948X/de1210Isup2.hkl
Contains datablock I

CCDC reference: 214413

Comment top

The functionalized pendant-arm derivatives of 1,4,7-triazacyclononane have been used as multidentate ligands for? enzyme simulations (Wieghardt et al., 1989), as models of myoglobin (Collman et al., 1997) and as building blocks for the construction of solid-state architectures (Tei et al., 1998; Tei et al., 2002). We chose to investigate macrocyclic frameworks with cyanoethyl groups as the pendant arms, because we believe that nitrile functionalized pendant-arms will promote the formation of multinuclear compounds that are similar to the active site in some enzymes. We report here the molecular and supramolecular structures of the ligand with C—H···N interactions. Cyano N atoms generally act as an acceptor, via an H atom, for aromatic C atoms? (Boitsov et al., 2002). However, in the supramolecular structure of the title compound, (I), the C—H···N interactions are between the methylene C—H atoms and the cyano N atoms.

The asymmetric unit of (I) consists of three unique molecules. The 1,4,7-tri(2-cyanoethyl)-1,4,7-triazacyclononane ion is protonated in the weak acidic solution of Mn3+, and the H atoms bound to atoms N3, N9 and N15, respectively. The cations and perchlorate anions are shown in Fig. 1.

The supramolecular structure of the ion is generated by a R44(30)S(10) motif and a C(10) chain. Cyano atom N36 of cation 3 (containing atoms C301 etc.) at (x, y, z) acts as an acceptor, via atom H213, for atom C207 of cation 2 (containing atoms C201 etc.) at (1 − x, 3/2 + y, 1/2 − z). Cyano atom N24 of cation 2 at (1 − x, 3/2 + y, 1/2 − z) acts as an acceptor, via atom H301, for atom C301 of cation 3 at (-x, 3/2 + y, 1/2 − z), and cyano atom N36 of cation 3 acts as an acceptor, via atom H213, for atom C207 of cation 2 at (−1 − x, −y, −z). Finally, cyano atom N24 of cation 2 at (−1 + x, y, z) acts as an acceptor, via atom H301, for atom C301 of cation 3 at (x, y, z), thus completing a centrosymmetric R44(30) ring, centered at (0, 1/2, 0). Cation 1 (containing atoms C101 etc.) at (−1 + x, −1 + y, z) and at (1/2 − x, 5/2 + y, 1/2 − z) links the rings? via C303—H305···N15 interactions. A C310—H316···N34 interaction in cation 3 generates an edge-fused S(10) ring (Fig. 2). The propogation of intermolecular C308—H316···N35 interactions between cations 3 produces a C(11) chain running parallel to the [010] direction (Fig. 3). The combination of two C(11) chains and R44(30) rings forms a `column' running parallel to the [010] direction (See Fig. 4).

There are also intermolecular C—H···O hydrogen bonds.

Experimental top

1,4,7-Tri(2-cyanoethyl)-1,4,7-triazacyclononane, (II), was prepared according to the method described by Bushnell et al. (1998). Compound (II) (0.1 mmol) was resolved? in methane (2 ml), and the solvent Mn(DMSO)6(ClO4)3 (0.1 mmol; DMSO is dimethyl sulfoxide) in methane (5 ml) was added dropwise. The resulting gray solid was removed by filtration. Single crystals of (I) were obtained by slow evaporation of the solvent. 1HNMR (CH3CN, p.p.m.): δ 2.75 (t, 6H, CH2—CN), 2.94 (m, 12H, N—CH2—CH2—N), 3.23 (t, 6H, N—CH2).

Refinement top

The positions of all H atoms were fixed geometrically, and H atoms were refined as riding, with C—H distances of 0.97 Å and N—H distances of 0.91 Å.

Computing details top

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

Figures top
[Figure 1] Fig. 1. The molecular configuration and atom-numbering scheme for (I), showing displacement ellipsoids at the 30% probability level. H atoms have been omitted for clarity.
[Figure 2] Fig. 2. Part of the crystal structure of (I), showing the formation of the R44(30) ring. [Symmetry codes: (i) 1 − x, 3/2 + y, 1/2 − z; (ii) −x., 2/3 + y, 1/2 − z; (iii) −1 − x, −y, −z; (iv) −1 + x, −1 + y, z; (v) 1/2 − x, 5/2 + y, 1/2 − z.] The perchlorate anions have been omitted for clarity.
[Figure 3] Fig. 3. Part of the crystal structure of (I), showing the formation of the C(11) chain.
[Figure 4] Fig. 4. Part of the crystal structure of (I), viewed along the a axis, showing the column formed by a combination of R44(30) rings and C(10) chains. The counter-anions have been omitted for clarity.
1,4,7-Tris(2-cyanoethyl)-4,7-triaza-1-azoniacyclononane perchlorate top
Crystal data top
C15H25N6+·ClO4F(000) = 2472
Mr = 388.86Dx = 1.338 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2265 reflections
a = 12.973 (7) Åθ = 2.4–17.2°
b = 9.708 (6) ŵ = 0.23 mm1
c = 46.04 (3) ÅT = 293 K
β = 92.544 (12)°Block, colourless
V = 5793 (6) Å30.32 × 0.22 × 0.15 mm
Z = 12
Data collection top
CCD area detector
diffractometer
10150 independent reflections
Radiation source: sealed tube5150 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
ϕ and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: empirical (using intensity measurements)
SHELXTL (Bruker, 2000)?
h = 1515
Tmin = 0.941, Tmax = 0.966k = 011
28731 measured reflectionsl = 054
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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.03P)2]
where P = (Fo2 + 2Fc2)/3
10150 reflections(Δ/σ)max < 0.001
703 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.24 e Å3
Crystal data top
C15H25N6+·ClO4V = 5793 (6) Å3
Mr = 388.86Z = 12
Monoclinic, P21/cMo Kα radiation
a = 12.973 (7) ŵ = 0.23 mm1
b = 9.708 (6) ÅT = 293 K
c = 46.04 (3) Å0.32 × 0.22 × 0.15 mm
β = 92.544 (12)°
Data collection top
CCD area detector
diffractometer
10150 independent reflections
Absorption correction: empirical (using intensity measurements)
SHELXTL (Bruker, 2000)?
5150 reflections with I > 2σ(I)
Tmin = 0.941, Tmax = 0.966Rint = 0.032
28731 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.091H-atom parameters constrained
S = 1.05Δρmax = 0.32 e Å3
10150 reflectionsΔρmin = 0.24 e Å3
703 parameters
Special details top

Experimental. The structure was solved by direct methods (Bruker, 2000) and successive difference Fourier syntheses.

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*/Ueq
C1010.82597 (15)1.0969 (2)0.24203 (4)0.0555 (6)
H1010.83431.13260.26170.067*
H1020.83001.17340.22860.067*
C1020.91004 (15)0.9938 (2)0.23654 (4)0.0516 (6)
H1030.97351.04220.23280.062*
H1040.92230.93700.25370.062*
C1030.89736 (15)0.7571 (2)0.21622 (4)0.0537 (6)
H1050.96740.74190.22380.064*
H1060.88860.70860.19790.064*
C1040.82281 (16)0.7012 (2)0.23730 (4)0.0562 (6)
H1070.82780.60150.23790.067*
H1080.84030.73620.25660.067*
C1050.65848 (16)0.7995 (2)0.25168 (5)0.0590 (6)
H1090.65760.73400.26760.071*
H1100.58770.81450.24470.071*
C1060.70385 (16)0.9355 (2)0.26293 (4)0.0588 (6)
H1110.65570.97990.27550.071*
H1120.76740.91810.27420.071*
C1070.63914 (17)1.1216 (2)0.23068 (5)0.0624 (6)
H1130.64191.19870.24410.075*
H1140.57441.07370.23300.075*
C1080.64223 (19)1.1746 (3)0.20032 (5)0.0762 (7)
H1150.70941.21490.19740.091*
H1160.63271.09860.18680.091*
C1090.5622 (2)1.2783 (3)0.19419 (6)0.0784 (8)
C1100.91763 (14)0.9560 (2)0.18372 (4)0.0483 (6)
H1170.90001.05270.18170.058*
H1180.88130.90690.16800.058*
C1111.03173 (15)0.9401 (2)0.18020 (5)0.0586 (6)
H1191.06910.99010.19560.070*
H1201.05040.84360.18190.070*
C1121.06091 (17)0.9922 (3)0.15208 (6)0.0603 (7)
C1130.66134 (17)0.6404 (2)0.21077 (5)0.0648 (7)
H1210.62360.58020.22330.078*
H1220.71120.58450.20100.078*
C1140.58685 (18)0.7017 (3)0.18829 (5)0.0719 (7)
H1230.55130.62810.17770.086*
H1240.53560.75580.19790.086*
C1150.6400 (2)0.7887 (3)0.16800 (6)0.0717 (8)
N110.72487 (13)1.02756 (18)0.23801 (4)0.0538 (5)
N120.88029 (11)0.90584 (17)0.21145 (3)0.0452 (4)
N130.71624 (13)0.74190 (18)0.22855 (4)0.0535 (5)
H1250.72450.81410.21630.064*
N140.50208 (19)1.3593 (3)0.18916 (5)0.0956 (8)
N151.08328 (15)1.0314 (2)0.13025 (5)0.0731 (6)
N160.68055 (18)0.8564 (3)0.15315 (5)0.0987 (8)
C2010.74927 (17)0.1787 (3)0.11601 (5)0.0658 (7)
H2010.68270.13870.11980.079*
H2020.77870.21510.13420.079*
C2020.81872 (19)0.0692 (3)0.10493 (5)0.0768 (7)
H2030.81370.01210.11700.092*
H2040.88950.10150.10660.092*
C2030.6913 (2)0.0393 (3)0.06929 (6)0.0893 (8)
H2050.65240.03330.08680.107*
H2060.70060.13570.06460.107*
C2040.6351 (2)0.0343 (3)0.04451 (6)0.0849 (8)
H2070.66790.01220.02660.102*
H2080.56470.00060.04280.102*
C2050.56906 (17)0.2339 (3)0.07070 (5)0.0690 (7)
H2090.54810.15810.08280.083*
H2100.50750.27670.06210.083*
C2060.62963 (17)0.3377 (3)0.08887 (5)0.0671 (7)
H2110.63010.42520.07870.081*
H2120.59640.35160.10710.081*
C2070.80762 (16)0.4073 (2)0.09945 (5)0.0618 (6)
H2130.81100.45870.08150.074*
H2140.87580.37010.10400.074*
C2080.77976 (17)0.5062 (3)0.12361 (5)0.0676 (7)
H2150.71100.54260.11950.081*
H2160.77940.45680.14190.081*
C2090.8532 (2)0.6194 (3)0.12610 (6)0.0743 (8)
C2100.8727 (2)0.0529 (3)0.06168 (6)0.1062 (10)
H2170.84100.11450.04730.127*
H2180.90460.10910.07700.127*
C2110.9528 (3)0.0270 (4)0.04804 (8)0.1292 (12)
H2190.99920.06140.06350.155*
H2200.99220.03650.03660.155*
C2120.9251 (3)0.1405 (4)0.02982 (9)0.1221 (13)
C2130.62718 (17)0.2677 (3)0.02092 (5)0.0738 (7)
H2210.63470.36410.02610.089*
H2220.68430.24320.00900.089*
C2140.52851 (19)0.2491 (3)0.00344 (5)0.0861 (8)
H2230.52490.15560.00400.103*
H2240.47090.26270.01590.103*
C2150.5198 (2)0.3446 (4)0.02061 (7)0.0932 (10)
N210.73515 (13)0.2917 (2)0.09475 (4)0.0577 (5)
N220.79333 (18)0.0300 (2)0.07382 (5)0.0815 (6)
N230.63334 (14)0.1829 (2)0.04806 (4)0.0700 (6)
H2250.69820.20120.05540.084*
N240.91336 (18)0.7030 (2)0.12693 (5)0.0932 (7)
N250.9094 (2)0.2369 (3)0.01851 (8)0.1342 (11)
N260.5178 (2)0.4254 (3)0.03876 (5)0.1155 (10)
C3010.18364 (17)0.6636 (2)0.13726 (5)0.0658 (7)
H3010.11000.65010.13380.079*
H3020.19420.73370.15210.079*
C3020.23461 (17)0.5299 (3)0.14700 (5)0.0661 (7)
H3030.30360.54830.15510.079*
H3040.19510.48720.16200.079*
C3030.13751 (17)0.3769 (2)0.11166 (5)0.0669 (7)
H3050.13160.28310.11860.080*
H3060.08200.43060.11940.080*
C3040.12883 (18)0.3787 (3)0.07916 (5)0.0705 (7)
H3070.16970.30400.07170.085*
H3080.05750.36310.07280.085*
C3050.10003 (19)0.6253 (3)0.07286 (5)0.0723 (7)
H3090.04740.59830.08610.087*
H3100.06540.65460.05480.087*
C3060.15841 (19)0.7431 (3)0.08559 (5)0.0720 (7)
H3110.10970.81080.09220.086*
H3120.19730.78570.07050.086*
C3070.30984 (18)0.8152 (2)0.11578 (5)0.0698 (7)
H3130.33180.81440.13620.084*
H3140.27930.90450.11140.084*
C3080.40249 (19)0.7955 (3)0.09765 (5)0.0770 (7)
H3150.38000.78020.07750.092*
H3160.44480.87790.09850.092*
C3090.4624 (2)0.6796 (3)0.10810 (6)0.0777 (8)
C3100.32738 (18)0.3346 (3)0.12101 (5)0.0749 (7)
H3170.32640.29250.10190.090*
H3180.39220.38370.12380.090*
C3110.32268 (19)0.2233 (3)0.14347 (6)0.0830 (8)
H3190.32550.26230.16290.100*
H3320.25950.17050.14080.100*
C3120.4144 (2)0.1348 (3)0.13906 (6)0.0824 (8)
C3130.2085 (2)0.4973 (3)0.03850 (5)0.0851 (8)
H3210.26690.43500.03980.102*
H3220.23380.58730.03300.102*
C3140.1328 (2)0.4469 (3)0.01528 (6)0.0983 (9)
H3230.10320.36040.02140.118*
H3240.07730.51320.01270.118*
C3150.1819 (3)0.4269 (3)0.01234 (7)0.1062 (11)
N310.23100 (14)0.70652 (19)0.11034 (4)0.0617 (5)
N320.23999 (13)0.4365 (2)0.12196 (4)0.0638 (5)
N330.16330 (15)0.5074 (2)0.06715 (4)0.0685 (5)
H3250.22020.52530.07880.082*
N340.50849 (19)0.5914 (3)0.11746 (5)0.1034 (8)
N350.48413 (18)0.0757 (3)0.13599 (5)0.0939 (8)
N360.2163 (3)0.4116 (3)0.03344 (6)0.1344 (11)
Cl10.97209 (5)0.37066 (7)0.186080 (14)0.06566 (18)
O110.87181 (17)0.3970 (3)0.19581 (5)0.1484 (9)
O120.95953 (15)0.3190 (2)0.15799 (4)0.1155 (7)
O131.01963 (18)0.2737 (2)0.20408 (5)0.1442 (9)
O141.02135 (15)0.4965 (2)0.18619 (4)0.1192 (7)
Cl20.27955 (6)0.05891 (8)0.039000 (16)0.0780 (2)
O210.3214 (3)0.0590 (3)0.03311 (5)0.1945 (14)
O220.2823 (3)0.1527 (3)0.01694 (6)0.1950 (12)
O230.1824 (2)0.0423 (4)0.03893 (10)0.2490 (19)
O240.2988 (3)0.0952 (3)0.06748 (6)0.2225 (16)
Cl30.31824 (5)0.90705 (8)0.208730 (15)0.0739 (2)
O310.28191 (16)1.0002 (3)0.18826 (5)0.1536 (9)
O320.32113 (16)0.7729 (2)0.19764 (4)0.1244 (7)
O330.24697 (16)0.9043 (2)0.23099 (4)0.1291 (7)
O340.41152 (16)0.9381 (2)0.22253 (5)0.1394 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1010.0578 (15)0.0500 (16)0.0590 (14)0.0102 (13)0.0043 (11)0.0113 (12)
C1020.0521 (14)0.0489 (15)0.0532 (14)0.0084 (12)0.0032 (11)0.0046 (12)
C1030.0550 (14)0.0418 (16)0.0643 (15)0.0077 (11)0.0033 (12)0.0018 (12)
C1040.0634 (16)0.0435 (15)0.0618 (14)0.0018 (12)0.0030 (12)0.0070 (12)
C1050.0609 (15)0.0550 (17)0.0618 (15)0.0060 (13)0.0104 (12)0.0037 (13)
C1060.0617 (15)0.0570 (17)0.0587 (14)0.0064 (12)0.0119 (11)0.0017 (13)
C1070.0616 (16)0.0569 (17)0.0688 (17)0.0026 (13)0.0046 (12)0.0050 (13)
C1080.0787 (19)0.073 (2)0.0772 (19)0.0063 (15)0.0004 (14)0.0014 (15)
C1090.084 (2)0.066 (2)0.0845 (19)0.0013 (17)0.0064 (16)0.0026 (17)
C1100.0474 (14)0.0445 (15)0.0535 (14)0.0043 (10)0.0060 (10)0.0021 (11)
C1110.0498 (14)0.0577 (16)0.0692 (16)0.0027 (11)0.0120 (12)0.0039 (13)
C1120.0526 (15)0.0558 (17)0.0737 (19)0.0004 (12)0.0179 (14)0.0095 (15)
C1130.0701 (16)0.0581 (18)0.0658 (15)0.0088 (13)0.0005 (13)0.0014 (14)
C1140.0703 (17)0.0706 (19)0.0740 (17)0.0115 (14)0.0074 (14)0.0011 (15)
C1150.0657 (19)0.074 (2)0.0741 (19)0.0074 (15)0.0082 (15)0.0049 (16)
N110.0543 (12)0.0488 (13)0.0589 (12)0.0078 (10)0.0084 (9)0.0046 (10)
N120.0500 (10)0.0387 (12)0.0469 (11)0.0024 (9)0.0024 (8)0.0003 (9)
N130.0597 (13)0.0478 (13)0.0534 (11)0.0047 (10)0.0058 (10)0.0075 (10)
N140.102 (2)0.0714 (19)0.1119 (19)0.0078 (14)0.0139 (15)0.0021 (15)
N150.0796 (15)0.0562 (15)0.0854 (16)0.0056 (11)0.0272 (12)0.0019 (12)
N160.0857 (18)0.107 (2)0.1031 (19)0.0073 (14)0.0049 (14)0.0365 (16)
C2010.0687 (17)0.0668 (19)0.0617 (15)0.0043 (14)0.0001 (13)0.0042 (14)
C2020.0855 (19)0.0685 (19)0.0763 (19)0.0093 (15)0.0017 (14)0.0168 (15)
C2030.109 (2)0.076 (2)0.083 (2)0.0065 (19)0.0042 (17)0.0041 (17)
C2040.099 (2)0.077 (2)0.0784 (19)0.0005 (17)0.0029 (16)0.0140 (17)
C2050.0619 (16)0.084 (2)0.0606 (15)0.0014 (14)0.0047 (13)0.0103 (14)
C2060.0606 (17)0.0763 (19)0.0637 (15)0.0064 (14)0.0054 (12)0.0110 (14)
C2070.0595 (15)0.0612 (17)0.0650 (15)0.0000 (13)0.0075 (12)0.0042 (13)
C2080.0619 (16)0.0630 (18)0.0780 (17)0.0002 (14)0.0045 (13)0.0112 (14)
C2090.0634 (19)0.063 (2)0.0959 (19)0.0021 (16)0.0010 (15)0.0118 (17)
C2100.118 (3)0.085 (2)0.117 (2)0.034 (2)0.031 (2)0.0158 (19)
C2110.113 (3)0.099 (3)0.178 (3)0.035 (2)0.041 (2)0.030 (3)
C2120.099 (3)0.095 (3)0.175 (4)0.024 (2)0.028 (2)0.036 (3)
C2130.0697 (17)0.089 (2)0.0622 (16)0.0084 (14)0.0042 (13)0.0104 (15)
C2140.080 (2)0.105 (2)0.0711 (18)0.0128 (16)0.0115 (15)0.0121 (18)
C2150.089 (2)0.117 (3)0.072 (2)0.026 (2)0.0087 (18)0.010 (2)
N210.0538 (13)0.0619 (14)0.0572 (12)0.0019 (11)0.0012 (9)0.0035 (11)
N220.0976 (18)0.0690 (17)0.0785 (16)0.0214 (14)0.0111 (13)0.0073 (12)
N230.0693 (14)0.0773 (17)0.0627 (14)0.0052 (11)0.0067 (11)0.0152 (13)
N240.0793 (17)0.0677 (18)0.133 (2)0.0077 (13)0.0086 (15)0.0144 (15)
N250.109 (2)0.101 (3)0.193 (3)0.0021 (19)0.0037 (19)0.044 (2)
N260.122 (2)0.146 (3)0.0774 (19)0.0350 (19)0.0093 (16)0.0058 (17)
C3010.0626 (16)0.0672 (19)0.0677 (16)0.0055 (13)0.0040 (13)0.0109 (14)
C3020.0596 (15)0.071 (2)0.0680 (16)0.0039 (14)0.0015 (12)0.0058 (15)
C3030.0633 (16)0.0553 (17)0.0817 (18)0.0061 (13)0.0035 (13)0.0080 (14)
C3040.0780 (17)0.0552 (19)0.0778 (19)0.0049 (14)0.0027 (13)0.0011 (14)
C3050.0815 (18)0.0603 (19)0.0737 (17)0.0121 (16)0.0133 (14)0.0003 (14)
C3060.0824 (18)0.0557 (18)0.0769 (17)0.0131 (14)0.0086 (14)0.0032 (14)
C3070.0726 (17)0.0569 (18)0.0801 (17)0.0044 (14)0.0041 (14)0.0073 (14)
C3080.0782 (19)0.068 (2)0.0851 (18)0.0026 (15)0.0104 (15)0.0090 (16)
C3090.070 (2)0.081 (3)0.083 (2)0.0036 (17)0.0057 (16)0.0136 (18)
C3100.0622 (17)0.0669 (19)0.0951 (19)0.0022 (14)0.0010 (14)0.0123 (16)
C3110.0679 (18)0.070 (2)0.111 (2)0.0019 (15)0.0008 (15)0.0165 (17)
C3120.064 (2)0.066 (2)0.116 (2)0.0004 (17)0.0125 (18)0.0041 (17)
C3130.110 (2)0.071 (2)0.0751 (19)0.0075 (16)0.0074 (17)0.0028 (15)
C3140.131 (3)0.085 (2)0.078 (2)0.0088 (19)0.0030 (19)0.0017 (17)
C3150.155 (3)0.087 (3)0.077 (2)0.011 (2)0.011 (2)0.005 (2)
N310.0652 (13)0.0527 (14)0.0669 (13)0.0072 (11)0.0017 (11)0.0054 (11)
N320.0540 (13)0.0553 (14)0.0818 (14)0.0008 (10)0.0001 (10)0.0019 (12)
N330.0829 (14)0.0542 (15)0.0681 (14)0.0004 (12)0.0023 (11)0.0024 (11)
N340.0929 (19)0.113 (2)0.1036 (19)0.0263 (16)0.0084 (14)0.0082 (17)
N350.0695 (17)0.0828 (19)0.1283 (19)0.0127 (14)0.0077 (15)0.0039 (15)
N360.209 (3)0.113 (2)0.083 (2)0.016 (2)0.030 (2)0.0047 (19)
Cl10.0809 (5)0.0518 (4)0.0638 (4)0.0006 (4)0.0020 (3)0.0024 (4)
O110.1226 (18)0.152 (2)0.177 (2)0.0022 (15)0.0718 (16)0.0020 (17)
O120.1377 (17)0.1248 (18)0.0819 (13)0.0248 (13)0.0192 (11)0.0270 (12)
O130.204 (2)0.0799 (16)0.1398 (18)0.0068 (15)0.0941 (17)0.0033 (14)
O140.1395 (17)0.0644 (14)0.1568 (18)0.0216 (13)0.0413 (14)0.0096 (13)
Cl20.0866 (5)0.0714 (6)0.0768 (5)0.0156 (4)0.0129 (4)0.0034 (4)
O210.346 (4)0.134 (2)0.1063 (17)0.136 (3)0.047 (2)0.0049 (16)
O220.291 (4)0.128 (2)0.169 (2)0.045 (2)0.053 (2)0.059 (2)
O230.108 (2)0.227 (4)0.412 (6)0.029 (2)0.007 (3)0.033 (3)
O240.391 (5)0.148 (3)0.123 (2)0.071 (3)0.043 (2)0.0540 (19)
Cl30.0720 (5)0.0763 (6)0.0724 (4)0.0075 (4)0.0072 (4)0.0004 (4)
O310.1253 (18)0.164 (2)0.171 (2)0.0157 (15)0.0060 (15)0.0938 (19)
O320.1571 (19)0.1055 (18)0.1090 (15)0.0002 (14)0.0109 (13)0.0400 (14)
O330.1357 (17)0.129 (2)0.1268 (17)0.0244 (14)0.0477 (14)0.0066 (14)
O340.0928 (15)0.125 (2)0.195 (2)0.0090 (13)0.0504 (14)0.0282 (16)
Geometric parameters (Å, º) top
C101—N111.478 (2)C210—N221.439 (3)
C101—C1021.509 (3)C210—C2111.461 (4)
C101—H1010.9700C210—H2170.9700
C101—H1020.9700C210—H2180.9700
C102—N121.474 (2)C211—C2121.422 (4)
C102—H1030.9700C211—H2190.9700
C102—H1040.9700C211—H2200.9700
C103—N121.476 (3)C212—N251.086 (4)
C103—C1041.502 (3)C213—C2141.492 (3)
C103—H1050.9700C213—N231.495 (3)
C103—H1060.9700C213—H2210.9700
C104—N131.477 (3)C213—H2220.9700
C104—H1070.9700C214—C2151.444 (4)
C104—H1080.9700C214—H2230.9700
C105—N131.442 (2)C214—H2240.9700
C105—C1061.527 (3)C215—N261.146 (4)
C105—H1090.9700N23—H2250.9100
C105—H1100.9700C301—N311.468 (3)
C106—N111.489 (2)C301—C3021.516 (3)
C106—H1110.9700C301—H3010.9700
C106—H1120.9700C301—H3020.9700
C107—N111.467 (3)C302—N321.471 (3)
C107—C1081.492 (3)C302—H3030.9700
C107—H1130.9700C302—H3040.9700
C107—H1140.9700C303—C3041.496 (3)
C108—C1091.465 (4)C303—N321.507 (3)
C108—H1150.9700C303—H3050.9700
C108—H1160.9700C303—H3060.9700
C109—N141.124 (3)C304—N331.446 (3)
C110—N121.468 (2)C304—H3070.9700
C110—C1111.504 (3)C304—H3080.9700
C110—H1170.9700C305—N331.439 (3)
C110—H1180.9700C305—C3061.478 (3)
C111—C1121.456 (3)C305—H3090.9700
C111—H1190.9700C305—H3100.9700
C111—H1200.9700C306—N311.489 (3)
C112—N151.125 (3)C306—H3110.9700
C113—N131.448 (3)C306—H3120.9700
C113—C1141.507 (3)C307—N311.483 (3)
C113—H1210.9700C307—C3081.506 (3)
C113—H1220.9700C307—H3130.9700
C114—C1151.455 (3)C307—H3140.9700
C114—H1230.9700C308—C3091.438 (4)
C114—H1240.9700C308—H3150.9700
C115—N161.099 (3)C308—H3160.9700
N13—H1250.9100C309—N341.120 (3)
C201—N211.477 (3)C310—C3111.499 (3)
C201—C2021.497 (3)C310—N321.506 (3)
C201—H2010.9700C310—H3170.9700
C201—H2020.9700C310—H3180.9700
C202—N221.504 (3)C311—C3121.489 (4)
C202—H2030.9700C311—H3190.9700
C202—H2040.9700C311—H3320.9700
C203—N221.491 (3)C312—N351.086 (3)
C203—C2041.506 (3)C313—N331.470 (3)
C203—H2050.9700C313—C3141.501 (3)
C203—H2060.9700C313—H3210.9700
C204—N231.453 (3)C313—H3220.9700
C204—H2070.9700C314—C3151.460 (4)
C204—H2080.9700C314—H3230.9700
C205—N231.450 (3)C314—H3240.9700
C205—C2061.509 (3)C315—N361.097 (3)
C205—H2090.9700N33—H3250.9100
C205—H2100.9700Cl1—O141.3785 (19)
C206—N211.454 (3)Cl1—O131.381 (2)
C206—H2110.9700Cl1—O121.3899 (19)
C206—H2120.9700Cl1—O111.418 (2)
C207—N211.473 (3)Cl2—O231.271 (3)
C207—C2081.525 (3)Cl2—O211.301 (2)
C207—H2130.9700Cl2—O221.366 (3)
C207—H2140.9700Cl2—O241.370 (3)
C208—C2091.455 (4)Cl3—O311.374 (2)
C208—H2150.9700Cl3—O341.375 (2)
C208—H2160.9700Cl3—O321.400 (2)
C209—N241.125 (3)Cl3—O331.411 (2)
N11—C101—C102108.72 (18)C211—C210—H218108.8
N11—C101—H101109.9H217—C210—H218107.7
C102—C101—H101109.9C212—C211—C210119.9 (3)
N11—C101—H102109.9C212—C211—H219107.3
C102—C101—H102109.9C210—C211—H219107.3
H101—C101—H102108.3C212—C211—H220107.3
N12—C102—C101110.44 (16)C210—C211—H220107.3
N12—C102—H103109.6H219—C211—H220106.9
C101—C102—H103109.6N25—C212—C211171.2 (5)
N12—C102—H104109.6C214—C213—N23113.4 (2)
C101—C102—H104109.6C214—C213—H221108.9
H103—C102—H104108.1N23—C213—H221108.9
N12—C103—C104110.68 (16)C214—C213—H222108.9
N12—C103—H105109.5N23—C213—H222108.9
C104—C103—H105109.5H221—C213—H222107.7
N12—C103—H106109.5C215—C214—C213111.9 (2)
C104—C103—H106109.5C215—C214—H223109.2
H105—C103—H106108.1C213—C214—H223109.2
N13—C104—C103110.42 (17)C215—C214—H224109.2
N13—C104—H107109.6C213—C214—H224109.2
C103—C104—H107109.6H223—C214—H224107.9
N13—C104—H108109.6N26—C215—C214175.5 (4)
C103—C104—H108109.6C206—N21—C207112.53 (19)
H107—C104—H108108.1C206—N21—C201116.09 (18)
N13—C105—C106112.38 (17)C207—N21—C201114.14 (17)
N13—C105—H109109.1C210—N22—C203109.8 (2)
C106—C105—H109109.1C210—N22—C202112.4 (2)
N13—C105—H110109.1C203—N22—C202113.7 (2)
C106—C105—H110109.1C205—N23—C204115.6 (2)
H109—C105—H110107.9C205—N23—C213113.70 (19)
N11—C106—C105109.79 (17)C204—N23—C213116.94 (19)
N11—C106—H111109.7C205—N23—H225102.6
C105—C106—H111109.7C204—N23—H225102.6
N11—C106—H112109.7C213—N23—H225102.6
C105—C106—H112109.7N31—C301—C302107.42 (18)
H111—C106—H112108.2N31—C301—H301110.2
N11—C107—C108112.26 (18)C302—C301—H301110.2
N11—C107—H113109.2N31—C301—H302110.2
C108—C107—H113109.2C302—C301—H302110.2
N11—C107—H114109.2H301—C301—H302108.5
C108—C107—H114109.2N32—C302—C301109.35 (18)
H113—C107—H114107.9N32—C302—H303109.8
C109—C108—C107111.7 (2)C301—C302—H303109.8
C109—C108—H115109.3N32—C302—H304109.8
C107—C108—H115109.3C301—C302—H304109.8
C109—C108—H116109.3H303—C302—H304108.3
C107—C108—H116109.3C304—C303—N32109.67 (18)
H115—C108—H116107.9C304—C303—H305109.7
N14—C109—C108178.6 (3)N32—C303—H305109.7
N12—C110—C111115.09 (16)C304—C303—H306109.7
N12—C110—H117108.5N32—C303—H306109.7
C111—C110—H117108.5H305—C303—H306108.2
N12—C110—H118108.5N33—C304—C303112.44 (19)
C111—C110—H118108.5N33—C304—H307109.1
H117—C110—H118107.5C303—C304—H307109.1
C112—C111—C110110.88 (18)N33—C304—H308109.1
C112—C111—H119109.5C303—C304—H308109.1
C110—C111—H119109.5H307—C304—H308107.8
C112—C111—H120109.5N33—C305—C306113.6 (2)
C110—C111—H120109.5N33—C305—H309108.8
H119—C111—H120108.1C306—C305—H309108.8
N15—C112—C111179.4 (3)N33—C305—H310108.8
N13—C113—C114113.9 (2)C306—C305—H310108.8
N13—C113—H121108.8H309—C305—H310107.7
C114—C113—H121108.8C305—C306—N31114.5 (2)
N13—C113—H122108.8C305—C306—H311108.6
C114—C113—H122108.8N31—C306—H311108.6
H121—C113—H122107.7C305—C306—H312108.6
C115—C114—C113111.3 (2)N31—C306—H312108.6
C115—C114—H123109.4H311—C306—H312107.6
C113—C114—H123109.4N31—C307—C308112.16 (19)
C115—C114—H124109.4N31—C307—H313109.2
C113—C114—H124109.4C308—C307—H313109.2
H123—C114—H124108.0N31—C307—H314109.2
N16—C115—C114178.5 (3)C308—C307—H314109.2
C107—N11—C101113.89 (18)H313—C307—H314107.9
C107—N11—C106112.83 (16)C309—C308—C307110.3 (2)
C101—N11—C106111.62 (16)C309—C308—H315109.6
C110—N12—C102113.85 (16)C307—C308—H315109.6
C110—N12—C103113.60 (15)C309—C308—H316109.6
C102—N12—C103114.71 (16)C307—C308—H316109.6
C105—N13—C113115.01 (18)H315—C308—H316108.1
C105—N13—C104114.41 (17)N34—C309—C308176.9 (3)
C113—N13—C104113.78 (18)C311—C310—N32113.55 (19)
C105—N13—H125103.9C311—C310—H317108.9
C113—N13—H125103.9N32—C310—H317108.9
C104—N13—H125103.9C311—C310—H318108.9
N21—C201—C202111.14 (18)N32—C310—H318108.9
N21—C201—H201109.4H317—C310—H318107.7
C202—C201—H201109.4C312—C311—C310105.3 (2)
N21—C201—H202109.4C312—C311—H319110.7
C202—C201—H202109.4C310—C311—H319110.7
H201—C201—H202108.0C312—C311—H332110.7
C201—C202—N22113.21 (19)C310—C311—H332110.7
C201—C202—H203108.9H319—C311—H332108.8
N22—C202—H203108.9N35—C312—C311176.6 (3)
C201—C202—H204108.9N33—C313—C314112.8 (2)
N22—C202—H204108.9N33—C313—H321109.0
H203—C202—H204107.7C314—C313—H321109.0
N22—C203—C204106.8 (2)N33—C313—H322109.0
N22—C203—H205110.4C314—C313—H322109.0
C204—C203—H205110.4H321—C313—H322107.8
N22—C203—H206110.4C315—C314—C313111.5 (3)
C204—C203—H206110.4C315—C314—H323109.3
H205—C203—H206108.6C313—C314—H323109.3
N23—C204—C203113.3 (2)C315—C314—H324109.3
N23—C204—H207108.9C313—C314—H324109.3
C203—C204—H207108.9H323—C314—H324108.0
N23—C204—H208108.9N36—C315—C314178.1 (4)
C203—C204—H208108.9C301—N31—C307111.75 (18)
H207—C204—H208107.7C301—N31—C306116.09 (18)
N23—C205—C206108.94 (19)C307—N31—C306111.58 (19)
N23—C205—H209109.9C302—N32—C310119.30 (18)
C206—C205—H209109.9C302—N32—C303114.29 (17)
N23—C205—H210109.9C310—N32—C303113.17 (19)
C206—C205—H210109.9C305—N33—C304115.39 (19)
H209—C205—H210108.3C305—N33—C313118.1 (2)
N21—C206—C205111.16 (19)C304—N33—C313115.33 (19)
N21—C206—H211109.4C305—N33—H325101.3
C205—C206—H211109.4C304—N33—H325101.3
N21—C206—H212109.4C313—N33—H325101.3
C205—C206—H212109.4O14—Cl1—O13114.01 (14)
H211—C206—H212108.0O14—Cl1—O12110.99 (13)
N21—C207—C208114.60 (18)O13—Cl1—O12110.09 (13)
N21—C207—H213108.6O14—Cl1—O11105.70 (14)
C208—C207—H213108.6O13—Cl1—O11108.96 (16)
N21—C207—H214108.6O12—Cl1—O11106.73 (14)
C208—C207—H214108.6O23—Cl2—O21108.2 (2)
H213—C207—H214107.6O23—Cl2—O2298.1 (2)
C209—C208—C207110.96 (19)O21—Cl2—O22114.00 (17)
C209—C208—H215109.4O23—Cl2—O24100.0 (2)
C207—C208—H215109.4O21—Cl2—O24111.44 (17)
C209—C208—H216109.4O22—Cl2—O24122.1 (2)
C207—C208—H216109.4O31—Cl3—O34116.15 (15)
H215—C208—H216108.0O31—Cl3—O32112.09 (16)
N24—C209—C208176.0 (3)O34—Cl3—O32109.58 (13)
N22—C210—C211113.9 (3)O31—Cl3—O33107.14 (14)
N22—C210—H217108.8O34—Cl3—O33105.08 (15)
C211—C210—H217108.8O32—Cl3—O33106.05 (14)
N22—C210—H218108.8
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N13—H125···N110.912.302.809 (3)115
N13—H125···N120.912.232.798 (3)120
N23—H225···N210.912.052.689 (3)126
N23—H225···N220.912.222.775 (3)119
N33—H325···N310.912.282.882 (3)123
N33—H325···N320.912.172.758 (3)122
C102—H104···O13i0.972.593.557 (4)171
C104—H108···O13i0.972.533.386 (4)147
C107—H114···O340.972.523.455 (4)162
C207—H213···N36ii0.972.563.513 (4)169
C211—H220···O23iii0.972.583.030 (5)108
C301—H301···N24iv0.972.613.538 (4)161
C302—H304···O14iv0.972.563.385 (4)143
C303—H305···N15v0.972.583.540 (4)169
C308—H316···N35vi0.972.623.387 (4)136
C310—H317···O240.972.503.396 (4)153
C310—H318···N340.972.543.435 (4)153
Symmetry codes: (i) x+2, y+1/2, z+1/2; (ii) x+1, y+1, z; (iii) x+1, y, z; (iv) x1, y, z; (v) x1, y1, z; (vi) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC15H25N6+·ClO4
Mr388.86
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)12.973 (7), 9.708 (6), 46.04 (3)
β (°) 92.544 (12)
V3)5793 (6)
Z12
Radiation typeMo Kα
µ (mm1)0.23
Crystal size (mm)0.32 × 0.22 × 0.15
Data collection
DiffractometerCCD area detector
diffractometer
Absorption correctionEmpirical (using intensity measurements)
SHELXTL (Bruker, 2000)?
Tmin, Tmax0.941, 0.966
No. of measured, independent and
observed [I > 2σ(I)] reflections
28731, 10150, 5150
Rint0.032
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.091, 1.05
No. of reflections10150
No. of parameters703
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.32, 0.24

Computer programs: SMART (Bruker, 2000), SMART, SAINT (Bruker, 2000), SHELXTL (Bruker, 2000), SHELXTL.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N13—H125···N110.91002.30002.809 (3)115.00
N13—H125···N120.91002.23002.798 (3)120.00
N23—H225···N210.91002.05002.689 (3)126.00
N23—H225···N220.91002.22002.775 (3)119.00
N33—H325···N310.91002.28002.882 (3)123.00
N33—H325···N320.91002.17002.758 (3)122.00
C102—H104···O13i0.97002.59003.557 (4)171.00
C104—H108···O13i0.97002.53003.386 (4)147.00
C107—H114···O340.97002.52003.455 (4)162.00
C207—H213···N36ii0.97002.56003.513 (4)169.00
C211—H220···O23iii0.97002.58003.030 (5)108.00
C301—H301···N24iv0.97002.61003.538 (4)161.00
C302—H304···O14iv0.97002.56003.385 (4)143.00
C303—H305···N15v0.97002.58003.540 (4)169.00
C308—H316···N35vi0.97002.62003.387 (4)136.00
C310—H317···O240.97002.50003.396 (4)153.00
C310—H318···N340.97002.54003.435 (4)153.00
Symmetry codes: (i) x+2, y+1/2, z+1/2; (ii) x+1, y+1, z; (iii) x+1, y, z; (iv) x1, y, z; (v) x1, y1, z; (vi) x, y+1, z.
 

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