Bis(2-pyridyl­ethyl)­ammonium perchlorate

The title compound, C₁₄H₁₈N₃⁺·ClO₄^-, a perchlorate salt of the monoprotonated form of bis(2-pyridyl­ethyl)­amine, has a structure in which one of the two H atoms on the amine N atom forms hydrogen bonds to the two pyridyl N atoms in a chelating fashion, while the second H atom on the amine is also used in hydrogen bonding to a perchlorate O atom.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in solvent or counterion
• R factor = 0.053
• wR factor = 0.158
• Data-to-parameter ratio = 14.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_302  Alert C Anion/Solvent Disorder .......................      27.00 Perc.

General Notes



ABSTM_02  When printed, the submitted absorption T values will be replaced
          by the scaled T values. Since the ratio of scaled T's is
          identical to the ratio of reported T values, the scaling does
          not imply a change to the absorption corrections used in the
          study.
          Ratio of Tmax expected/reported      1.110
          Tmax scaled      0.957 Tmin scaled      0.837


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 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-pyridylethyl)ammonium perchlorate

Crystal data

C14H18N3^+·ClO4^−	Z = 2
Mr = 327.76	F(000) = 344
Triclinic, P1	Dx = 1.358 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4093 (11) Å	Cell parameters from 53 reflections
b = 9.0987 (11) Å	θ = 4.9–12.5°
c = 12.161 (2) Å	µ = 0.26 mm^−1
α = 88.477 (13)°	T = 293 K
β = 82.986 (17)°	Needle, colorless
γ = 80.079 (12)°	0.80 × 0.34 × 0.17 mm
V = 801.5 (2) Å^3

Data collection

Siemens P4S diffractometer	2318 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.016
Graphite monochromator	θmax = 27.5°, θmin = 2.8°
ω scans	h = −9→0
Absorption correction: part of the refinement model (ΔF) (SHELXTL; Sheldrick, 1997)	k = −11→11
Tmin = 0.754, Tmax = 0.862	l = −15→15
3967 measured reflections	3 standard reflections every 97 reflections
3681 independent reflections	intensity decay: 0.4%

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.158	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0698P)^2 + 0.1918P] where P = (Fo^2 + 2Fc^2)/3
3681 reflections	(Δ/σ)max = 0.030
257 parameters	Δρmax = 0.21 e Å^−3
41 restraints	Δρmin = −0.30 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	0.82685 (9)	−0.02675 (6)	0.24388 (6)	0.0691 (3)
O1	0.6683 (2)	−0.0960 (2)	0.25550 (17)	0.0971 (7)
O2	0.9382 (6)	−0.0733 (7)	0.1440 (4)	0.151 (3)	0.590 (4)
O3	0.9281 (7)	−0.0670 (7)	0.3345 (4)	0.157 (3)	0.590 (4)
O4	0.7712 (3)	0.13008 (19)	0.2417 (6)	0.0689 (14)	0.590 (4)
O2A	0.7816 (5)	0.1165 (5)	0.2923 (8)	0.102 (6)	0.203 (6)
O3A	0.9675 (6)	−0.1147 (7)	0.2972 (7)	0.123 (7)	0.203 (6)
O4A	0.8892 (9)	−0.0130 (10)	0.12991 (17)	0.069 (4)	0.203 (6)
O2B	0.9758 (5)	−0.1213 (6)	0.1841 (8)	0.188 (12)	0.207 (6)
O3B	0.8730 (10)	0.0004 (11)	0.35024 (19)	0.092 (4)	0.207 (6)
O4B	0.7890 (6)	0.1102 (6)	0.1865 (8)	0.101 (5)	0.207 (6)
N1A	0.3104 (4)	0.4551 (3)	0.3721 (2)	0.0829 (7)
N1B	0.2178 (3)	0.4278 (2)	0.1077 (2)	0.0756 (6)
N2	0.3583 (3)	0.1917 (2)	0.24854 (17)	0.0635 (5)
H0A	0.4823	0.1696	0.2402	0.076*
H0B	0.3269	0.2917	0.2456	0.076*
C1A	0.2556 (5)	0.6032 (3)	0.3820 (3)	0.0876 (9)
H1AA	0.2576	0.6613	0.3179	0.105*
C2A	0.1968 (4)	0.6732 (4)	0.4814 (3)	0.0873 (9)
H2AA	0.1602	0.7762	0.4846	0.105*
C3A	0.1930 (5)	0.5890 (4)	0.5755 (3)	0.0955 (10)
H3AB	0.1549	0.6337	0.6443	0.115*
C4A	0.2464 (4)	0.4364 (4)	0.5674 (3)	0.0833 (9)
H4AA	0.2428	0.3769	0.6307	0.100*
C5A	0.3050 (4)	0.3729 (3)	0.4653 (2)	0.0720 (7)
C6A	0.3680 (5)	0.2069 (3)	0.4509 (2)	0.0861 (9)
H6AA	0.3350	0.1573	0.5202	0.103*
H6AB	0.5015	0.1874	0.4354	0.103*
C7A	0.2879 (4)	0.1394 (3)	0.3597 (3)	0.0825 (9)
H7AA	0.3194	0.0315	0.3634	0.099*
H7AB	0.1545	0.1660	0.3707	0.099*
C1B	0.1593 (4)	0.5744 (3)	0.0881 (3)	0.0825 (9)
H1BA	0.0961	0.6329	0.1468	0.099*
C2B	0.1876 (4)	0.6411 (3)	−0.0124 (3)	0.0858 (9)
H2BA	0.1444	0.7422	−0.0223	0.103*
C3B	0.2817 (5)	0.5552 (4)	−0.0990 (3)	0.0923 (10)
H3BA	0.3054	0.5979	−0.1684	0.111*
C4B	0.3405 (4)	0.4057 (4)	−0.0822 (3)	0.0822 (8)
H4BA	0.4023	0.3457	−0.1405	0.099*
C5B	0.3071 (4)	0.3453 (3)	0.0219 (2)	0.0692 (7)
C6B	0.3680 (5)	0.1814 (3)	0.0449 (3)	0.0810 (9)
H6BA	0.3347	0.1244	−0.0135	0.097*
H6BB	0.5015	0.1618	0.0414	0.097*
C7B	0.2886 (4)	0.1265 (3)	0.1538 (3)	0.0808 (8)
H7BA	0.3205	0.0187	0.1566	0.097*
H7BB	0.1552	0.1526	0.1607	0.097*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0693 (4)	0.0483 (3)	0.0871 (5)	−0.0021 (3)	−0.0100 (3)	0.0018 (3)
O1	0.0931 (15)	0.0833 (14)	0.1215 (18)	−0.0307 (12)	−0.0170 (13)	0.0009 (13)
O2	0.125 (4)	0.096 (4)	0.211 (6)	−0.015 (3)	0.076 (4)	−0.088 (4)
O3	0.138 (5)	0.132 (5)	0.223 (7)	−0.039 (4)	−0.112 (5)	0.109 (5)
O4	0.084 (3)	0.0438 (18)	0.071 (4)	−0.0002 (16)	0.007 (2)	0.0005 (17)
O2A	0.150 (13)	0.070 (8)	0.080 (11)	−0.007 (8)	0.006 (8)	−0.042 (7)
O3A	0.081 (9)	0.087 (9)	0.189 (17)	0.042 (8)	−0.048 (10)	−0.031 (11)
O4A	0.099 (8)	0.060 (6)	0.037 (5)	−0.002 (5)	0.017 (5)	−0.009 (4)
O2B	0.142 (15)	0.088 (10)	0.28 (3)	0.071 (10)	0.054 (17)	0.039 (15)
O3B	0.108 (9)	0.058 (7)	0.123 (10)	−0.014 (6)	−0.076 (8)	0.028 (6)
O4B	0.127 (10)	0.088 (8)	0.061 (9)	0.028 (7)	0.020 (7)	0.033 (7)
N1A	0.1047 (19)	0.0644 (14)	0.0739 (16)	−0.0041 (13)	−0.0034 (13)	0.0005 (12)
N1B	0.0795 (15)	0.0586 (12)	0.0843 (16)	0.0081 (11)	−0.0198 (12)	−0.0059 (11)
N2	0.0613 (12)	0.0470 (10)	0.0789 (14)	−0.0019 (9)	−0.0062 (10)	−0.0007 (10)
C1A	0.104 (2)	0.0633 (17)	0.094 (2)	−0.0069 (16)	−0.0179 (18)	0.0009 (16)
C2A	0.087 (2)	0.0681 (18)	0.106 (3)	0.0019 (15)	−0.0269 (18)	−0.0187 (18)
C3A	0.098 (2)	0.097 (2)	0.087 (2)	0.0092 (19)	−0.0241 (19)	−0.028 (2)
C4A	0.086 (2)	0.087 (2)	0.0708 (19)	0.0044 (16)	−0.0162 (15)	−0.0017 (15)
C5A	0.0718 (17)	0.0685 (16)	0.0712 (18)	−0.0005 (13)	−0.0061 (14)	−0.0026 (13)
C6A	0.106 (2)	0.0706 (17)	0.0706 (18)	0.0048 (16)	0.0013 (17)	0.0110 (14)
C7A	0.089 (2)	0.0573 (15)	0.094 (2)	−0.0082 (14)	0.0123 (17)	0.0016 (14)
C1B	0.0780 (19)	0.0612 (16)	0.105 (2)	0.0082 (14)	−0.0258 (17)	−0.0082 (16)
C2B	0.087 (2)	0.0617 (16)	0.113 (3)	−0.0043 (15)	−0.0433 (19)	0.0097 (17)
C3B	0.103 (2)	0.084 (2)	0.097 (2)	−0.0209 (19)	−0.038 (2)	0.0189 (19)
C4B	0.087 (2)	0.081 (2)	0.079 (2)	−0.0076 (16)	−0.0211 (16)	−0.0066 (16)
C5B	0.0666 (16)	0.0612 (15)	0.0809 (19)	−0.0017 (12)	−0.0253 (14)	−0.0053 (13)
C6B	0.100 (2)	0.0592 (15)	0.082 (2)	0.0053 (15)	−0.0281 (17)	−0.0121 (14)
C7B	0.0841 (19)	0.0522 (14)	0.110 (2)	−0.0077 (13)	−0.0289 (17)	−0.0092 (14)

Geometric parameters (Å, º)

Cl1—O2B	1.4126 (17)	C3A—H3AB	0.93
Cl1—O3	1.4132 (17)	C4A—C5A	1.372 (4)
Cl1—O3A	1.4133 (17)	C4A—H4AA	0.93
Cl1—O2	1.4134 (17)	C5A—C6A	1.510 (4)
Cl1—O2A	1.4138 (17)	C6A—C7A	1.511 (4)
Cl1—O4B	1.4144 (17)	C6A—H6AA	0.97
Cl1—O3B	1.4158 (17)	C6A—H6AB	0.97
Cl1—O4	1.4159 (17)	C7A—H7AA	0.97
Cl1—O4A	1.4159 (17)	C7A—H7AB	0.97
Cl1—O1	1.4162 (15)	C1B—C2B	1.360 (5)
N1A—C5A	1.342 (4)	C1B—H1BA	0.9300
N1A—C1A	1.343 (4)	C2B—C3B	1.371 (5)
N1B—C5B	1.338 (3)	C2B—H2BA	0.93
N1B—C1B	1.353 (3)	C3B—C4B	1.373 (4)
N2—C7A	1.485 (3)	C3B—H3BA	0.93
N2—C7B	1.495 (3)	C4B—C5B	1.378 (4)
N2—H0A	0.90	C4B—H4BA	0.93
N2—H0B	0.90	C5B—C6B	1.511 (4)
C1A—C2A	1.370 (4)	C6B—C7B	1.491 (4)
C1A—H1AA	0.93	C6B—H6BA	0.97
C2A—C3A	1.360 (5)	C6B—H6BB	0.97
C2A—H2AA	0.93	C7B—H7BA	0.97
C3A—C4A	1.380 (4)	C7B—H7BB	0.97
O2B—Cl1—O3	83.5 (3)	C3A—C2A—H2AA	120.7
O2B—Cl1—O3A	58.1 (5)	C1A—C2A—H2AA	120.7
O3—Cl1—O2	109.67 (9)	C2A—C3A—C4A	119.0 (3)
O3A—Cl1—O2	85.7 (4)	C2A—C3A—H3AB	120.5
O2B—Cl1—O2A	140.92 (14)	C4A—C3A—H3AB	120.5
O3—Cl1—O2A	85.7 (4)	C5A—C4A—C3A	119.6 (3)
O3A—Cl1—O2A	109.65 (9)	C5A—C4A—H4AA	120.2
O2—Cl1—O2A	129.6 (3)	C3A—C4A—H4AA	120.2
O2B—Cl1—O4B	109.68 (9)	N1A—C5A—C4A	121.8 (3)
O3—Cl1—O4B	131.2 (2)	N1A—C5A—C6A	115.9 (2)
O3A—Cl1—O4B	141.07 (14)	C4A—C5A—C6A	122.3 (3)
O2—Cl1—O4B	83.5 (3)	C5A—C6A—C7A	114.6 (2)
O2A—Cl1—O4B	54.0 (5)	C5A—C6A—H6AA	108.6
O2B—Cl1—O3B	109.55 (9)	C7A—C6A—H6AA	108.6
O3A—Cl1—O3B	54.5 (5)	C5A—C6A—H6AB	108.6
O2—Cl1—O3B	131.5 (2)	C7A—C6A—H6AB	108.6
O2A—Cl1—O3B	58.3 (5)	H6AA—C6A—H6AB	107.6
O4B—Cl1—O3B	109.39 (9)	N2—C7A—C6A	111.7 (3)
O2B—Cl1—O4	131.5 (2)	N2—C7A—H7AA	109.3
O3—Cl1—O4	109.46 (9)	C6A—C7A—H7AA	109.3
O3A—Cl1—O4	130.0 (3)	N2—C7A—H7AB	109.3
O2—Cl1—O4	109.44 (9)	C6A—C7A—H7AB	109.3
O3B—Cl1—O4	83.5 (3)	H7AA—C7A—H7AB	107.9
O2B—Cl1—O4A	54.3 (5)	N1B—C1B—C2B	123.8 (3)
O3—Cl1—O4A	130.0 (3)	N1B—C1B—H1BA	118.1
O3A—Cl1—O4A	109.47 (9)	C2B—C1B—H1BA	118.1
O2A—Cl1—O4A	109.46 (9)	C1B—C2B—C3B	118.2 (3)
O4B—Cl1—O4A	58.5 (5)	C1B—C2B—H2BA	120.9
O3B—Cl1—O4A	141.38 (14)	C3B—C2B—H2BA	120.9
O4—Cl1—O4A	85.8 (3)	C2B—C3B—C4B	119.4 (3)
O2B—Cl1—O1	109.58 (9)	C2B—C3B—H3BA	120.3
O3—Cl1—O1	109.48 (9)	C4B—C3B—H3BA	120.3
O3A—Cl1—O1	109.50 (9)	C3B—C4B—C5B	119.3 (3)
O2—Cl1—O1	109.58 (9)	C3B—C4B—H4BA	120.3
O2A—Cl1—O1	109.43 (9)	C5B—C4B—H4BA	120.3
O4B—Cl1—O1	109.36 (9)	N1B—C5B—C4B	122.1 (3)
O3B—Cl1—O1	109.26 (9)	N1B—C5B—C6B	116.4 (3)
O4—Cl1—O1	109.19 (9)	C4B—C5B—C6B	121.5 (3)
O4A—Cl1—O1	109.30 (9)	C7B—C6B—C5B	115.2 (2)
C5A—N1A—C1A	117.5 (3)	C7B—C6B—H6BA	108.5
C5B—N1B—C1B	117.2 (3)	C5B—C6B—H6BA	108.5
C7A—N2—C7B	114.8 (2)	C7B—C6B—H6BB	108.5
C7A—N2—H0A	108.6	C5B—C6B—H6BB	108.5
C7B—N2—H0A	108.6	H6BA—C6B—H6BB	107.5
C7A—N2—H0B	108.6	C6B—C7B—N2	111.8 (2)
C7B—N2—H0B	108.6	C6B—C7B—H7BA	109.3
H0A—N2—H0B	107.6	N2—C7B—H7BA	109.3
N1A—C1A—C2A	123.4 (3)	C6B—C7B—H7BB	109.3
N1A—C1A—H1AA	118.3	N2—C7B—H7BB	109.3
C2A—C1A—H1AA	118.3	H7BA—C7B—H7BB	107.9
C3A—C2A—C1A	118.6 (3)
C5A—N1A—C1A—C2A	0.6 (5)	C5B—N1B—C1B—C2B	−0.6 (4)
N1A—C1A—C2A—C3A	−0.2 (5)	N1B—C1B—C2B—C3B	−0.4 (5)
C1A—C2A—C3A—C4A	−0.7 (5)	C1B—C2B—C3B—C4B	1.3 (5)
C2A—C3A—C4A—C5A	1.1 (5)	C2B—C3B—C4B—C5B	−1.3 (5)
C1A—N1A—C5A—C4A	−0.2 (5)	C1B—N1B—C5B—C4B	0.6 (4)
C1A—N1A—C5A—C6A	−179.9 (3)	C1B—N1B—C5B—C6B	−178.9 (2)
C3A—C4A—C5A—N1A	−0.6 (5)	C3B—C4B—C5B—N1B	0.3 (5)
C3A—C4A—C5A—C6A	179.1 (3)	C3B—C4B—C5B—C6B	179.7 (3)
N1A—C5A—C6A—C7A	−46.9 (4)	N1B—C5B—C6B—C7B	11.8 (4)
C4A—C5A—C6A—C7A	133.4 (3)	C4B—C5B—C6B—C7B	−167.7 (3)
C7B—N2—C7A—C6A	178.5 (2)	C5B—C6B—C7B—N2	−67.3 (3)
C5A—C6A—C7A—N2	67.8 (3)	C7A—N2—C7B—C6B	−178.8 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H0A···O4B	0.90	2.26	3.151 (6)	170
N2—H0A···O4	0.90	2.11	3.005 (3)	172
N2—H0A···O2A	0.90	2.35	3.200 (6)	158
N2—H0A···O1	0.90	2.58	3.178 (3)	124
N2—H0B···N1A	0.90	2.15	2.810 (3)	130
N2—H0B···N1B	0.90	2.21	2.846 (3)	127