Bis­[2-(2-pyridinio)­ethyl]­ammonium triperchlorate

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.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](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

---

Computing details

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

Crystal data

C14H20N3^3+·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) Å^3

Data collection

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

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.113	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0397P)^2 + 0.8913P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

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···O24^i	0.90	2.10	2.912 (3)	150
N—H0A···O23^ii	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.