In the title compound, C14H20N33+·3ClO4-, all three N atoms (one amine and two pyridyl) are protonated. At least one ClO4- ion is hydrogen bonded to each of the three N atoms. The H atom on the amine N atom shows the greatest distance to a ClO4- O atom (2.47 Å), while those on the two pyridyl N atoms are at distances ranging from 1.87 to 2.38 Å.
Supporting information
CCDC reference: 200754
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- Disorder in solvent or counterion
- R factor = 0.043
- wR factor = 0.113
- Data-to-parameter ratio = 10.3
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
ABSTM_02 Alert C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
Tmin and Tmax reported: 0.682 0.909
Tmin' and Tmax expected: 0.788 0.943
RR' = 0.898
Please check that your absorption correction is appropriate.
PLAT_214 Alert C Atom O31A (Anion/Solvent) ADP max/min Ratio 4.10 prolate
PLAT_302 Alert C Anion/Solvent Disorder ....................... 17.00 Perc.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
3 Alert Level C = Please check
Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Bis[2-(2-pyridinio)ethyl]ammonium triperchlorate
top
Crystal data top
C14H20N33+·3ClO4− | Z = 2 |
Mr = 528.68 | F(000) = 544 |
Triclinic, P1 | Dx = 1.620 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.6789 (8) Å | Cell parameters from 56 reflections |
b = 8.7858 (10) Å | θ = 4.8–13.2° |
c = 15.1139 (15) Å | µ = 0.49 mm−1 |
α = 105.984 (8)° | T = 293 K |
β = 94.188 (8)° | Plate, colorless |
γ = 99.581 (9)° | 0.48 × 0.24 × 0.12 mm |
V = 1083.82 (19) Å3 | |
Data collection top
Siemens P4S diffractometer | 2885 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.015 |
Graphite monochromator | θmax = 25.0°, θmin = 2.6° |
2θ/ω scans | h = 0→10 |
Absorption correction: part of the refinement model (ΔF) (SHELXTL; Sheldrick, 1997) | k = −9→9 |
Tmin = 0.682, Tmax = 0.909 | l = −17→17 |
4007 measured reflections | 3 standard reflections every 97 reflections |
3743 independent reflections | intensity decay: 0.9% |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.113 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0397P)2 + 0.8913P] where P = (Fo2 + 2Fc2)/3 |
3743 reflections | (Δ/σ)max = 0.027 |
365 parameters | Δρmax = 0.29 e Å−3 |
121 restraints | Δρmin = −0.37 e Å−3 |
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 | Uiso*/Ueq | Occ. (<1) |
Cl1 | 0.94946 (8) | 0.36638 (8) | 0.19112 (5) | 0.03984 (19) | |
Cl2 | 1.29355 (9) | 0.60854 (10) | 0.46375 (5) | 0.0469 (2) | |
Cl3 | 0.44716 (10) | −0.07948 (11) | 0.16660 (6) | 0.0572 (2) | |
O11 | 0.8503 (3) | 0.3501 (4) | 0.2613 (2) | 0.0797 (9) | |
O12 | 1.0425 (3) | 0.5264 (3) | 0.21648 (18) | 0.0673 (7) | |
O13 | 0.8532 (3) | 0.3371 (3) | 0.10462 (17) | 0.0617 (6) | |
O14 | 1.0501 (2) | 0.2515 (3) | 0.18211 (17) | 0.0540 (6) | |
O21 | 1.3672 (4) | 0.7165 (3) | 0.4178 (2) | 0.0834 (9) | |
O22 | 1.1265 (3) | 0.5846 (4) | 0.4426 (2) | 0.0839 (9) | |
O23 | 1.3344 (4) | 0.6695 (4) | 0.56077 (17) | 0.0778 (8) | |
O24 | 1.3432 (3) | 0.4571 (3) | 0.43013 (17) | 0.0623 (7) | |
O31 | 0.5179 (6) | 0.0377 (6) | 0.1257 (4) | 0.080 (2) | 0.510 (4) |
O32 | 0.5076 (10) | −0.2205 (6) | 0.1353 (5) | 0.117 (3) | 0.510 (4) |
O33 | 0.2830 (4) | −0.1106 (11) | 0.1422 (5) | 0.136 (4) | 0.510 (4) |
O34 | 0.4825 (8) | −0.0177 (9) | 0.2640 (2) | 0.121 (3) | 0.510 (4) |
O31A | 0.4320 (11) | −0.0606 (16) | 0.0770 (4) | 0.161 (9) | 0.358 (10) |
O32A | 0.5907 (8) | −0.1295 (15) | 0.1824 (7) | 0.091 (4) | 0.358 (10) |
O33A | 0.3217 (10) | −0.2003 (10) | 0.1728 (8) | 0.117 (5) | 0.358 (10) |
O34A | 0.4441 (14) | 0.0662 (7) | 0.2333 (7) | 0.137 (7) | 0.358 (10) |
O31B | 0.337 (3) | 0.018 (3) | 0.1993 (17) | 0.091 (13) | 0.131 (10) |
O32B | 0.410 (4) | −0.2263 (16) | 0.1883 (18) | 0.123 (13) | 0.131 (10) |
O33B | 0.5998 (15) | 0.001 (4) | 0.2089 (16) | 0.19 (2) | 0.131 (10) |
O34B | 0.440 (3) | −0.111 (3) | 0.0695 (3) | 0.091 (11) | 0.131 (10) |
N1A | 1.0282 (3) | 0.8252 (3) | 0.36280 (18) | 0.0454 (6) | |
H1AA | 1.0527 | 0.7326 | 0.3579 | 0.054* | |
N1B | 0.2929 (3) | 0.1579 (3) | 0.02273 (17) | 0.0392 (6) | |
H1BA | 0.3506 | 0.1064 | 0.0476 | 0.047* | |
N | 0.5606 (3) | 0.4690 (3) | 0.29318 (16) | 0.0383 (6) | |
H0A | 0.5271 | 0.4737 | 0.3487 | 0.046* | |
H0B | 0.6237 | 0.3961 | 0.2823 | 0.046* | |
C2A | 1.1386 (4) | 0.9432 (4) | 0.3526 (3) | 0.0572 (9) | |
H2AA | 1.2386 | 0.9243 | 0.3413 | 0.069* | |
C3A | 1.1036 (5) | 1.0907 (4) | 0.3591 (2) | 0.0568 (9) | |
H3AA | 1.1785 | 1.1737 | 0.3516 | 0.068* | |
C4A | 0.9555 (5) | 1.1143 (4) | 0.3767 (2) | 0.0599 (10) | |
H4AA | 0.9293 | 1.2143 | 0.3813 | 0.072* | |
C5A | 0.8456 (4) | 0.9917 (4) | 0.3879 (2) | 0.0523 (8) | |
H5AA | 0.7458 | 1.0095 | 0.4007 | 0.063* | |
C6A | 0.8820 (3) | 0.8426 (3) | 0.38010 (18) | 0.0368 (6) | |
C7A | 0.7710 (4) | 0.6977 (4) | 0.3865 (2) | 0.0468 (8) | |
H7AA | 0.7145 | 0.7274 | 0.4397 | 0.056* | |
H7AB | 0.8295 | 0.6164 | 0.3944 | 0.056* | |
C8A | 0.6548 (3) | 0.6299 (4) | 0.2982 (2) | 0.0402 (7) | |
H8AA | 0.5843 | 0.7042 | 0.2963 | 0.048* | |
H8AB | 0.7119 | 0.6200 | 0.2447 | 0.048* | |
C2B | 0.1740 (4) | 0.0726 (4) | −0.0409 (2) | 0.0502 (8) | |
H2BA | 0.1557 | −0.0395 | −0.0580 | 0.060* | |
C3B | 0.0789 (4) | 0.1492 (4) | −0.0813 (2) | 0.0534 (8) | |
H3BA | −0.0047 | 0.0905 | −0.1263 | 0.064* | |
C4B | 0.1083 (4) | 0.3154 (4) | −0.0543 (2) | 0.0534 (9) | |
H4BA | 0.0428 | 0.3700 | −0.0800 | 0.064* | |
C5B | 0.2348 (4) | 0.4010 (4) | 0.0109 (2) | 0.0439 (7) | |
H5BA | 0.2566 | 0.5132 | 0.0278 | 0.053* | |
C6B | 0.3291 (3) | 0.3198 (3) | 0.05089 (18) | 0.0339 (6) | |
C7B | 0.4678 (3) | 0.3977 (4) | 0.1235 (2) | 0.0415 (7) | |
H7BA | 0.5099 | 0.5043 | 0.1190 | 0.050* | |
H7BB | 0.5495 | 0.3340 | 0.1130 | 0.050* | |
C8B | 0.4205 (3) | 0.4115 (4) | 0.21985 (19) | 0.0378 (6) | |
H8BA | 0.3487 | 0.4862 | 0.2331 | 0.045* | |
H8BB | 0.3654 | 0.3069 | 0.2214 | 0.045* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0370 (4) | 0.0409 (4) | 0.0431 (4) | 0.0124 (3) | 0.0062 (3) | 0.0117 (3) |
Cl2 | 0.0502 (5) | 0.0582 (5) | 0.0424 (4) | 0.0236 (4) | 0.0111 (3) | 0.0225 (4) |
Cl3 | 0.0606 (5) | 0.0681 (6) | 0.0558 (5) | 0.0250 (4) | 0.0141 (4) | 0.0298 (4) |
O11 | 0.0690 (17) | 0.122 (2) | 0.0814 (19) | 0.0498 (17) | 0.0430 (15) | 0.0562 (18) |
O12 | 0.0842 (18) | 0.0371 (13) | 0.0682 (16) | 0.0013 (12) | −0.0068 (14) | 0.0053 (11) |
O13 | 0.0585 (15) | 0.0638 (15) | 0.0585 (15) | 0.0086 (12) | −0.0144 (12) | 0.0183 (12) |
O14 | 0.0431 (12) | 0.0473 (13) | 0.0741 (16) | 0.0202 (10) | 0.0079 (11) | 0.0151 (11) |
O21 | 0.103 (2) | 0.0723 (18) | 0.096 (2) | 0.0217 (16) | 0.0419 (18) | 0.0476 (17) |
O22 | 0.0494 (15) | 0.122 (3) | 0.095 (2) | 0.0315 (16) | 0.0066 (14) | 0.0478 (19) |
O23 | 0.100 (2) | 0.098 (2) | 0.0411 (14) | 0.0552 (18) | 0.0016 (13) | 0.0097 (13) |
O24 | 0.0730 (17) | 0.0533 (14) | 0.0672 (16) | 0.0254 (13) | 0.0200 (13) | 0.0175 (12) |
O31 | 0.071 (4) | 0.084 (4) | 0.121 (6) | 0.032 (3) | 0.026 (4) | 0.075 (4) |
O32 | 0.187 (9) | 0.055 (4) | 0.152 (8) | 0.066 (5) | 0.099 (7) | 0.056 (5) |
O33 | 0.050 (4) | 0.223 (12) | 0.158 (9) | 0.008 (6) | −0.021 (5) | 0.112 (9) |
O34 | 0.129 (7) | 0.174 (9) | 0.053 (4) | 0.042 (6) | 0.007 (4) | 0.012 (5) |
O31A | 0.208 (16) | 0.31 (2) | 0.078 (9) | 0.227 (17) | 0.080 (9) | 0.119 (11) |
O32A | 0.099 (8) | 0.117 (10) | 0.098 (8) | 0.061 (7) | 0.020 (6) | 0.072 (7) |
O33A | 0.097 (10) | 0.121 (10) | 0.126 (10) | −0.008 (7) | 0.030 (8) | 0.037 (7) |
O34A | 0.173 (17) | 0.062 (7) | 0.170 (15) | 0.036 (8) | 0.040 (13) | 0.013 (7) |
O31B | 0.13 (3) | 0.08 (2) | 0.09 (2) | 0.06 (2) | 0.08 (2) | 0.039 (17) |
O32B | 0.148 (17) | 0.108 (15) | 0.134 (16) | 0.042 (10) | −0.004 (10) | 0.064 (10) |
O33B | 0.18 (2) | 0.19 (2) | 0.19 (2) | 0.035 (11) | 0.017 (10) | 0.048 (12) |
O34B | 0.087 (14) | 0.108 (14) | 0.082 (14) | 0.045 (9) | 0.020 (9) | 0.014 (8) |
N1A | 0.0516 (16) | 0.0374 (14) | 0.0511 (16) | 0.0165 (12) | 0.0119 (12) | 0.0132 (12) |
N1B | 0.0416 (14) | 0.0364 (14) | 0.0430 (14) | 0.0142 (11) | 0.0057 (11) | 0.0132 (11) |
N | 0.0311 (12) | 0.0485 (15) | 0.0373 (13) | 0.0058 (11) | 0.0019 (10) | 0.0177 (11) |
C2A | 0.050 (2) | 0.062 (2) | 0.066 (2) | 0.0105 (17) | 0.0195 (17) | 0.0261 (18) |
C3A | 0.070 (2) | 0.050 (2) | 0.049 (2) | −0.0034 (18) | 0.0101 (17) | 0.0204 (16) |
C4A | 0.092 (3) | 0.0391 (19) | 0.054 (2) | 0.0233 (19) | 0.0093 (19) | 0.0171 (16) |
C5A | 0.054 (2) | 0.052 (2) | 0.056 (2) | 0.0239 (17) | 0.0070 (16) | 0.0152 (16) |
C6A | 0.0395 (16) | 0.0424 (16) | 0.0263 (14) | 0.0085 (13) | −0.0019 (12) | 0.0078 (12) |
C7A | 0.0454 (18) | 0.0532 (19) | 0.0388 (17) | −0.0006 (15) | −0.0043 (14) | 0.0166 (14) |
C8A | 0.0360 (15) | 0.0440 (17) | 0.0401 (16) | 0.0020 (13) | −0.0019 (13) | 0.0166 (13) |
C2B | 0.055 (2) | 0.0390 (17) | 0.0470 (19) | 0.0017 (15) | 0.0043 (16) | 0.0023 (14) |
C3B | 0.0475 (19) | 0.062 (2) | 0.0415 (18) | −0.0016 (16) | −0.0032 (15) | 0.0093 (16) |
C4B | 0.0471 (19) | 0.071 (2) | 0.052 (2) | 0.0195 (17) | 0.0011 (16) | 0.0312 (18) |
C5B | 0.0512 (18) | 0.0373 (16) | 0.0477 (18) | 0.0110 (14) | 0.0084 (15) | 0.0177 (14) |
C6B | 0.0335 (15) | 0.0382 (16) | 0.0306 (14) | 0.0077 (12) | 0.0089 (11) | 0.0092 (12) |
C7B | 0.0342 (15) | 0.0470 (18) | 0.0395 (16) | 0.0017 (13) | 0.0037 (13) | 0.0103 (13) |
C8B | 0.0269 (14) | 0.0475 (17) | 0.0371 (16) | 0.0035 (12) | 0.0026 (12) | 0.0116 (13) |
Geometric parameters (Å, º) top
Cl1—O14 | 1.426 (2) | Cl3—O31 | 1.420 (3) |
Cl1—O12 | 1.434 (2) | N1A—C6A | 1.339 (4) |
Cl1—O13 | 1.434 (2) | N1A—C2A | 1.340 (4) |
Cl1—O11 | 1.436 (2) | N1B—C2B | 1.323 (4) |
Cl2—O23 | 1.411 (3) | N1B—C6B | 1.341 (4) |
Cl2—O21 | 1.420 (3) | N—C8A | 1.490 (4) |
Cl2—O22 | 1.429 (3) | N—C8B | 1.501 (3) |
Cl2—O24 | 1.437 (2) | C2A—C3A | 1.359 (5) |
Cl3—O34A | 1.400 (3) | C3A—C4A | 1.369 (5) |
Cl3—O32 | 1.401 (3) | C4A—C5A | 1.371 (5) |
Cl3—O33 | 1.406 (3) | C5A—C6A | 1.374 (4) |
Cl3—O33B | 1.407 (4) | C6A—C7A | 1.494 (4) |
Cl3—O31A | 1.409 (3) | C7A—C8A | 1.522 (4) |
Cl3—O32B | 1.410 (4) | C2B—C3B | 1.358 (5) |
Cl3—O34B | 1.410 (4) | C3B—C4B | 1.377 (5) |
Cl3—O31B | 1.411 (4) | C4B—C5B | 1.378 (4) |
Cl3—O34 | 1.412 (3) | C5B—C6B | 1.380 (4) |
Cl3—O32A | 1.414 (3) | C6B—C7B | 1.497 (4) |
Cl3—O33A | 1.416 (3) | C7B—C8B | 1.521 (4) |
| | | |
O14—Cl1—O12 | 109.79 (15) | O32A—Cl3—O33A | 108.5 (2) |
O14—Cl1—O13 | 109.80 (15) | O32—Cl3—O31 | 109.3 (2) |
O12—Cl1—O13 | 109.11 (15) | O33—Cl3—O31 | 108.9 (2) |
O14—Cl1—O11 | 108.85 (15) | O34—Cl3—O31 | 108.9 (2) |
O12—Cl1—O11 | 109.95 (18) | C6A—N1A—C2A | 124.0 (3) |
O13—Cl1—O11 | 109.33 (17) | C2B—N1B—C6B | 124.2 (3) |
O23—Cl2—O21 | 111.3 (2) | C8A—N—C8B | 114.4 (2) |
O23—Cl2—O22 | 109.05 (18) | N1A—C2A—C3A | 119.7 (3) |
O21—Cl2—O22 | 109.24 (18) | C2A—C3A—C4A | 118.4 (3) |
O23—Cl2—O24 | 109.77 (15) | C3A—C4A—C5A | 120.6 (3) |
O21—Cl2—O24 | 108.16 (16) | C4A—C5A—C6A | 120.3 (3) |
O22—Cl2—O24 | 109.30 (18) | N1A—C6A—C5A | 117.0 (3) |
O32—Cl3—O33 | 110.8 (2) | N1A—C6A—C7A | 117.5 (3) |
O34A—Cl3—O31A | 110.3 (3) | C5A—C6A—C7A | 125.5 (3) |
O33B—Cl3—O32B | 109.6 (3) | C6A—C7A—C8A | 109.4 (2) |
O33B—Cl3—O34B | 109.6 (3) | N—C8A—C7A | 111.5 (2) |
O32B—Cl3—O34B | 109.4 (3) | N1B—C2B—C3B | 119.9 (3) |
O33B—Cl3—O31B | 109.6 (3) | C2B—C3B—C4B | 118.8 (3) |
O32B—Cl3—O31B | 109.3 (3) | C3B—C4B—C5B | 120.0 (3) |
O34B—Cl3—O31B | 109.3 (3) | C4B—C5B—C6B | 119.8 (3) |
O32—Cl3—O34 | 109.7 (2) | N1B—C6B—C5B | 117.3 (3) |
O33—Cl3—O34 | 109.3 (2) | N1B—C6B—C7B | 117.4 (2) |
O34A—Cl3—O32A | 110.0 (3) | C5B—C6B—C7B | 125.3 (3) |
O31A—Cl3—O32A | 109.1 (2) | C6B—C7B—C8B | 110.7 (2) |
O34A—Cl3—O33A | 109.6 (3) | N—C8B—C7B | 111.9 (2) |
O31A—Cl3—O33A | 109.3 (3) | | |
| | | |
C6A—N1A—C2A—C3A | −0.6 (5) | C6B—N1B—C2B—C3B | −0.7 (5) |
N1A—C2A—C3A—C4A | 0.6 (5) | N1B—C2B—C3B—C4B | −0.3 (5) |
C2A—C3A—C4A—C5A | 0.1 (5) | C2B—C3B—C4B—C5B | 1.6 (5) |
C3A—C4A—C5A—C6A | −0.9 (5) | C3B—C4B—C5B—C6B | −1.9 (5) |
C2A—N1A—C6A—C5A | −0.2 (4) | C2B—N1B—C6B—C5B | 0.4 (4) |
C2A—N1A—C6A—C7A | 178.0 (3) | C2B—N1B—C6B—C7B | −179.9 (3) |
C4A—C5A—C6A—N1A | 0.9 (5) | C4B—C5B—C6B—N1B | 0.9 (4) |
C4A—C5A—C6A—C7A | −177.1 (3) | C4B—C5B—C6B—C7B | −178.8 (3) |
N1A—C6A—C7A—C8A | −104.3 (3) | N1B—C6B—C7B—C8B | −83.8 (3) |
C5A—C6A—C7A—C8A | 73.7 (4) | C5B—C6B—C7B—C8B | 95.9 (3) |
C8B—N—C8A—C7A | 167.1 (2) | C8A—N—C8B—C7B | 59.3 (3) |
C6A—C7A—C8A—N | 169.6 (2) | C6B—C7B—C8B—N | 172.5 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1AA···O22 | 0.86 | 2.19 | 2.916 (4) | 142 |
N1A—H1AA···O12 | 0.86 | 2.38 | 2.957 (3) | 125 |
N1B—H1BA···O31A | 0.86 | 1.87 | 2.704 (9) | 162 |
N1B—H1BA···O31 | 0.86 | 2.07 | 2.915 (6) | 166 |
N1B—H1BA···O34B | 0.86 | 2.27 | 3.09 (2) | 157 |
N—H0A···O24i | 0.90 | 2.10 | 2.912 (3) | 150 |
N—H0A···O23ii | 0.90 | 2.47 | 2.957 (3) | 114 |
N—H0B···O11 | 0.90 | 2.10 | 2.902 (3) | 148 |
Symmetry codes: (i) x−1, y, z; (ii) −x+2, −y+1, −z+1. |