N,N′-Bis(2-ammonio­benz­yl)ethane-1,2-diammonium–nitrate–perchlorate (1/1.5/2.5)

Garza Rodríguez, L.A.; Bernès, S.; Nájera Martínez, B.; Elizondo Martínez, P.; Pérez Rodríguez, N.

doi:10.1107/S160053680904519X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o2995

doi:10.1107/S160053680904519X

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N,N′-Bis(2-ammoniobenzyl)ethane-1,2-diammonium–nitrate–perchlorate (1/1.5/2.5)

Luis Angel Garza Rodríguez,^a Sylvain Bernès,^b Blanca Nájera Martínez,^a Perla Elizondo Martínez ^a and Nancy Pérez Rodríguez ^a ^*

^aLaboratorio de Química Industrial, CELAES, Facultad de Ciencias Químicas, UANL, Pedro de Alba S/N, 66451 San Nicolás de los Garza, NL, Mexico, and ^bDEP Facultad de Ciencias Químicas, UANL, Guerrero y Progreso S/N, Col. Treviño, 64570 Monterrey, NL, Mexico
^*Correspondence e-mail: sylvain_bernes@hotmail.com

(Received 8 October 2009; accepted 28 October 2009; online 4 November 2009)

The title compound, C₁₆H₂₆N₄⁴⁺·2.5ClO₄⁻·1.5NO₃⁻, is an organic salt in which the cation is a fully protonated tetramine. The cation lies on an inversion center and, as a consequence, both benzene rings are parallel. The central chain is found in an all-trans arrangement, a conformation different from that observed in the crystal structure of the non-protonated molecule. The charges are balanced by a mixture of nitrate and perchlorate ions. One site is occupied by an ordered perchlorate ion, while the other contains both nitrate and perchlorate ions, with occupancies of 0.75 and 0.25, respectively. In the crystal, the NH₂⁺ groups of the cation form N—H⋯O hydrogen bonds with the anions. The NH₃⁺ groups also behave as donor groups, allowing the building of chains along [100], alternating cations and disordered anions being connected via N—H⋯O hydrogen bonds.

Related literature

For the structure of the free tetramine, see: Rodríguez de Barbarín et al. (2007 ). For the use of polyaza ligands for depolymerization of poly(ethylene terephthalate), see: Carta et al. (2003 ); Parra et al. (2004 ); Pohorely et al. (2006 ).

Experimental

Crystal data

C₁₆H₂₆N₄⁴⁺·2.5ClO₄⁻·1.5NO₃⁻
M_r = 616.05
Monoclinic, P 2₁ /n
a = 8.427 (3) Å
b = 12.637 (3) Å
c = 11.834 (3) Å
β = 106.97 (2)°
V = 1205.4 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.41 mm⁻¹
T = 298 K
0.6 × 0.4 × 0.4 mm

Data collection

Siemens P4 diffractometer
Absorption correction: none
6392 measured reflections
2125 independent reflections
1757 reflections with I > 2σ(I)
R_int = 0.057
3 standard reflections every 97 reflections intensity decay: <1%

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.119
S = 1.14
2125 reflections
218 parameters
8 restraints
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N9—H9A⋯O2	0.90	2.05	2.872 (4)	151
N9—H9B⋯O7	0.90	2.02	2.89 (5)	163
N9—H9B⋯O13	0.90	1.98	2.836 (13)	157
N1—H1A⋯O5ⁱ	0.89	2.04	2.91 (3)	165
N1—H1A⋯O12ⁱ	0.89	2.05	2.920 (13)	164
N1—H1B⋯O8ⁱⁱ	0.89	1.90	2.78 (2)	170
N1—H1B⋯O14ⁱⁱ	0.89	2.14	3.026 (11)	174
N1—H1C⋯O1ⁱⁱⁱ	0.89	2.39	3.207 (4)	153
Symmetry codes: (i) x-1, y, z; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) -x, -y+1, -z+1.

Data collection: XSCANS (Siemens, 1996 ); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL-Plus (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL-Plus; molecular graphics: SHELXTL-Plus and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXTL-Plus.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680904519X/vm2008sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680904519X/vm2008Isup2.hkl

checkCIF report

Comment top

Poly(ethylene terephthalate) (PET) is a thermoplastic material, which has been increasingly used in the industry during the last decades. Its low degradability makes this material highly contaminant to the environment (Carta et al., 2003). Currently, many efforts are devoted to reduce the amount of waste PET that reaches the landfillings. Some processes are able to recycle PET into highly valued carbon materials (Parra et al., 2004), used to generate heat and electricity (Pohorely et al., 2006). An interesting approach known as 'chemical recycling' is based on the depolymerization of PET through solvolytic chain cleavage. Five processes have been probed, with different depolymerizing agents: methanolysis, glycolysis, hydrolysis, aminolysis and ammonolysis. Several reactions used catalyst, among them zinc compounds.

Our group is involved in the search for reactions relevant to the chemical degradation of PET, using acyclic polyaza zinc complexes ZnLX₂ (X = ClO₄^-, NO₃^-; L = polyaza ligand), which gave excellent results. The title salt appeared during an attempt to prepare a bimetallic catalyst. Previous works showed that complex CuL[CuCl₄] can be obtained as the product of the transmetallation of MnL(NO₃)₂ with Cu(ClO₄)₂.6H₂O in ethanol, with an excess of aqueous HCl. The same transmetallation procedure, using Zn(ClO₄)₂.6H₂O in acidic ethanol afforded pale yellow crystals as a subproduct, which were identified as the title salt by X-ray diffraction.

The salt is composed of a tetracation and a mixture of nitrate and perchlorate anions (Fig. 1). The presence of both anions in the material was confirmed by IR spectroscopy, as spectra include characteristic vibrations for these ions. The cation is fully protonated and is placed on an inversion center. As a consequence, benzene rings are parallel by symmetry. The 6-membered chain linking the benzene fragments is found in the all-trans extended conformation, contrasting with the trans-gauche-trans conformation observed in the solid-sate for the non-protonated tetramine (Rodríguez de Barbarín et al., 2007). Anions are found in two sites. One site is occupied by a non disordered perchlorate, Cl1. The other site contains a mixture of nitrate (N11) and perchlorate (Cl2), with occupancies 3/4 and 1/4, respectively (Fig. 1, inset). Because they are involved in hydrogen bonds, anions do not present orientational disorder.

NH₂⁺ and NH₃⁺ groups have different functions regarding hydrogen bonding in the crystal. NH₂⁺ donors groups are connected to anions within the asymmetric unit, forming N—H···O hydrogen bonds (Fig. 1). NH₃⁺ groups also serve as donors for N—H···O hydrogen bonds, connecting symmetry related cations via anions, to form a one-dimensional supramolecular structure where cations and anions alternate in the [100] direction (Fig. 2).

Related literature top

For the structure of the free tetramine, see: Rodríguez de Barbarín et al. (2007). For the use of polyaza ligands for depolymerization of poly(ethylene terephthalate), see: Carta et al. (2003); Parra et al. (2004); Pohorely et al. (2006).

Experimental top

A 25 ml flask was charged with MnL(NO₃)₂ [279 mg; L is the free tetramine corresponding to the title cation (Rodríguez de Barbarín et al., 2007)] and ethanol (9 ml) and the mixture was stirred for 5 min., giving a white suspension. Salt Zn(ClO₄)₂.6H₂O was added (919 mg) and the reaction further stirred for 3 min., affording a quite clear solution. Immediately, 200 mg of concentrated HCl was added, and the mixture turned to a translucent light yellow solution, which was cooled for 4 d. Light yellow-green crystals were formed over this period, which were isolated and washed with cold ethanol, diethyl ether and finally air dried. Yield 68% (26.2 mg), m.p. 160 °C (dec.). IR (KBr, cm^-1) ν(CH₂) 2942, 2787, ν(NO₃) 1383, ν(ClO₄) 1084, 940.

Computing details top

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS (Siemens, 1996); data reduction: XSCANS (Siemens, 1996); program(s) used to solve structure: SHELXTL-Plus (Sheldrick, 2008); program(s) used to refine structure: SHELXTL-Plus (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL-Plus (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of the title compound, with displacement ellipsoids at the 30% probability level. Dashed lines represent hydrogen bonds in the asymmetric unit. The inset shows the anionic site with two disordered anions: nitrate N11 (occupancy = 3/4) and perchlorate Cl2 (occupancy = 1/4).
	Fig. 2. A part of the crystal structure of the title compound, with hydrogen bonds represented with dashed lines. Green anions are perchlorate and blue anions are nitrate. For the sake of clarity, some perchlorate ions have been omitted (hanging contacts). The crystal is viewed almost along [010].

N,N'-Bis(2-ammoniobenzyl)ethane-1,2-diammonium–nitrate– perchlorate (1/1.5/2.5) top

Crystal data top

C₁₆H₂₆N₄⁴⁺·2.5ClO₄⁻·1.5NO₃⁻	F(000) = 638
M_r = 616.05	D_x = 1.697 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 73 reflections
a = 8.427 (3) Å	θ = 5.0–12.4°
b = 12.637 (3) Å	µ = 0.41 mm⁻¹
c = 11.834 (3) Å	T = 298 K
β = 106.97 (2)°	Irregular, pale yellow
V = 1205.4 (6) Å³	0.6 × 0.4 × 0.4 mm
Z = 2

Data collection top

Siemens P4 diffractometer	R_int = 0.057
Radiation source: fine-focus sealed tube	θ_max = 25.1°, θ_min = 2.4°
Graphite monochromator	h = −10→10
ω scans	k = −15→15
6392 measured reflections	l = −14→14
2125 independent reflections	3 standard reflections every 97 reflections
1757 reflections with I > 2σ(I)	intensity decay: <1%

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H-atom parameters constrained
S = 1.14	w = 1/[σ²(F_o²) + (0.0221P)² + 1.6735P] where P = (F_o² + 2F_c²)/3
2125 reflections	(Δ/σ)_max < 0.001
218 parameters	Δρ_max = 0.25 e Å⁻³
8 restraints	Δρ_min = −0.27 e Å⁻³
0 constraints

Crystal data top

C₁₆H₂₆N₄⁴⁺·2.5ClO₄⁻·1.5NO₃⁻	V = 1205.4 (6) Å³
M_r = 616.05	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.427 (3) Å	µ = 0.41 mm⁻¹
b = 12.637 (3) Å	T = 298 K
c = 11.834 (3) Å	0.6 × 0.4 × 0.4 mm
β = 106.97 (2)°

Data collection top

Siemens P4 diffractometer	R_int = 0.057
6392 measured reflections	3 standard reflections every 97 reflections
2125 independent reflections	intensity decay: <1%
1757 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.050	8 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 1.14	Δρ_max = 0.25 e Å⁻³
2125 reflections	Δρ_min = −0.27 e Å⁻³
218 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1	−0.1084 (4)	0.6532 (2)	0.2742 (2)	0.0430 (7)
H1A	−0.2090	0.6242	0.2538	0.065*
H1B	−0.1163	0.7215	0.2897	0.065*
H1C	−0.0445	0.6208	0.3381	0.065*
C2	−0.0347 (4)	0.6416 (2)	0.1763 (3)	0.0326 (7)
C3	−0.1440 (4)	0.6359 (2)	0.0652 (3)	0.0399 (8)
H3A	−0.2578	0.6371	0.0546	0.048*
C4	−0.0826 (5)	0.6283 (2)	−0.0310 (3)	0.0434 (8)
H4A	−0.1553	0.6235	−0.1070	0.052*
C5	0.0852 (5)	0.6280 (3)	−0.0143 (3)	0.0430 (8)
H5A	0.1263	0.6245	−0.0791	0.052*
C6	0.1929 (4)	0.6327 (2)	0.0979 (3)	0.0394 (8)
H6A	0.3066	0.6313	0.1082	0.047*
C7	0.1348 (4)	0.6396 (2)	0.1969 (3)	0.0311 (7)
C8	0.2604 (4)	0.6487 (2)	0.3159 (3)	0.0371 (7)
H8A	0.2095	0.6834	0.3696	0.044*
H8B	0.3513	0.6928	0.3091	0.044*
N9	0.3283 (3)	0.5437 (2)	0.3671 (2)	0.0350 (6)
H9A	0.2457	0.5053	0.3806	0.042*
H9B	0.3660	0.5085	0.3140	0.042*
C10	0.4644 (4)	0.5534 (3)	0.4787 (3)	0.0380 (8)
H10A	0.4225	0.5862	0.5384	0.046*
H10B	0.5509	0.5985	0.4662	0.046*
Cl1	−0.00237 (10)	0.35712 (6)	0.40133 (7)	0.0396 (2)
O1	−0.1221 (4)	0.3829 (3)	0.4604 (3)	0.0752 (9)
O2	0.0116 (4)	0.4419 (2)	0.3253 (2)	0.0643 (8)
O3	0.1540 (4)	0.3438 (2)	0.4887 (2)	0.0648 (8)
O4	−0.0495 (4)	0.2635 (2)	0.3332 (3)	0.0647 (8)
Cl2	0.5512 (9)	0.4371 (6)	0.1804 (8)	0.0358 (15)	0.25
O5	0.587 (4)	0.5336 (15)	0.244 (2)	0.039 (7)	0.25
O6	0.5011 (19)	0.4701 (12)	0.0603 (8)	0.083 (4)	0.25
O7	0.415 (4)	0.394 (4)	0.211 (4)	0.083 (14)	0.25
O8	0.675 (2)	0.3628 (14)	0.186 (2)	0.052 (5)	0.25
N11	0.5525 (14)	0.4327 (9)	0.2076 (9)	0.068 (4)	0.75
O12	0.5925 (19)	0.5250 (7)	0.2380 (11)	0.071 (4)	0.75
O13	0.4469 (14)	0.3860 (9)	0.2416 (13)	0.056 (2)	0.75
O14	0.6277 (12)	0.3811 (8)	0.1526 (9)	0.099 (3)	0.75

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0417 (16)	0.0511 (17)	0.0434 (15)	0.0065 (14)	0.0236 (13)	0.0043 (13)
C2	0.0406 (18)	0.0254 (14)	0.0364 (16)	0.0035 (13)	0.0186 (14)	0.0037 (13)
C3	0.0373 (18)	0.0331 (16)	0.0472 (19)	0.0030 (14)	0.0089 (15)	0.0045 (15)
C4	0.062 (2)	0.0306 (16)	0.0344 (17)	0.0060 (16)	0.0086 (16)	0.0029 (14)
C5	0.065 (3)	0.0361 (18)	0.0336 (17)	0.0020 (17)	0.0231 (17)	0.0038 (14)
C6	0.0451 (19)	0.0333 (16)	0.0475 (18)	−0.0014 (15)	0.0255 (16)	0.0056 (15)
C7	0.0393 (18)	0.0221 (14)	0.0347 (15)	−0.0016 (13)	0.0153 (13)	0.0033 (12)
C8	0.0392 (18)	0.0305 (16)	0.0421 (17)	−0.0037 (14)	0.0128 (15)	−0.0009 (14)
N9	0.0333 (15)	0.0368 (14)	0.0337 (13)	−0.0012 (11)	0.0081 (12)	−0.0022 (11)
C10	0.0333 (18)	0.0418 (18)	0.0355 (17)	−0.0007 (14)	0.0047 (14)	−0.0050 (14)
Cl1	0.0461 (5)	0.0334 (4)	0.0467 (5)	−0.0010 (4)	0.0250 (4)	0.0020 (3)
O1	0.069 (2)	0.088 (2)	0.089 (2)	0.0045 (17)	0.0545 (18)	−0.0055 (18)
O2	0.084 (2)	0.0519 (16)	0.0603 (16)	−0.0161 (15)	0.0263 (15)	0.0158 (13)
O3	0.0577 (18)	0.0691 (18)	0.0606 (16)	0.0068 (15)	0.0065 (14)	−0.0013 (14)
O4	0.0669 (19)	0.0407 (14)	0.086 (2)	−0.0074 (13)	0.0213 (16)	−0.0149 (14)
Cl2	0.028 (3)	0.033 (3)	0.051 (3)	−0.006 (2)	0.018 (2)	−0.007 (2)
O5	0.039 (13)	0.049 (16)	0.039 (9)	0.007 (10)	0.026 (9)	0.002 (9)
O6	0.105 (11)	0.110 (10)	0.037 (6)	−0.004 (9)	0.027 (7)	0.017 (7)
O7	0.059 (14)	0.12 (2)	0.08 (3)	−0.036 (15)	0.030 (17)	−0.020 (16)
O8	0.029 (7)	0.032 (6)	0.094 (12)	0.010 (6)	0.019 (7)	−0.005 (7)
N11	0.070 (6)	0.079 (7)	0.060 (6)	0.024 (5)	0.026 (4)	−0.002 (4)
O12	0.082 (8)	0.029 (4)	0.118 (7)	−0.005 (4)	0.055 (6)	−0.006 (4)
O13	0.060 (5)	0.052 (3)	0.062 (6)	−0.016 (3)	0.028 (5)	−0.003 (3)
O14	0.104 (7)	0.097 (5)	0.122 (8)	0.031 (4)	0.075 (6)	−0.015 (5)

Geometric parameters (Å, º) top

N1—C2	1.473 (4)	N9—C10	1.480 (4)
N1—H1A	0.8900	N9—H9A	0.9000
N1—H1B	0.8900	N9—H9B	0.9000
N1—H1C	0.8900	C10—C10ⁱ	1.503 (6)
C2—C3	1.369 (4)	C10—H10A	0.9700
C2—C7	1.378 (4)	C10—H10B	0.9700
C3—C4	1.385 (5)	Cl1—O4	1.421 (3)
C3—H3A	0.9300	Cl1—O1	1.423 (3)
C4—C5	1.369 (5)	Cl1—O2	1.426 (3)
C4—H4A	0.9300	Cl1—O3	1.428 (3)
C5—C6	1.374 (5)	Cl2—O8	1.389 (9)
C5—H5A	0.9300	Cl2—O7	1.409 (10)
C6—C7	1.398 (4)	Cl2—O5	1.417 (10)
C6—H6A	0.9300	Cl2—O6	1.422 (9)
C7—C8	1.498 (4)	N11—O14	1.222 (8)
C8—N9	1.501 (4)	N11—O13	1.229 (8)
C8—H8A	0.9700	N11—O12	1.238 (8)
C8—H8B	0.9700

C2—N1—H1A	109.5	H8A—C8—H8B	107.8
C2—N1—H1B	109.5	C10—N9—C8	113.1 (2)
H1A—N1—H1B	109.5	C10—N9—H9A	109.0
C2—N1—H1C	109.5	C8—N9—H9A	109.0
H1A—N1—H1C	109.5	C10—N9—H9B	109.0
H1B—N1—H1C	109.5	C8—N9—H9B	109.0
C3—C2—C7	122.8 (3)	H9A—N9—H9B	107.8
C3—C2—N1	116.1 (3)	N9—C10—C10ⁱ	110.7 (3)
C7—C2—N1	121.0 (3)	N9—C10—H10A	109.5
C2—C3—C4	119.0 (3)	C10ⁱ—C10—H10A	109.5
C2—C3—H3A	120.5	N9—C10—H10B	109.5
C4—C3—H3A	120.5	C10ⁱ—C10—H10B	109.5
C5—C4—C3	120.0 (3)	H10A—C10—H10B	108.1
C5—C4—H4A	120.0	O4—Cl1—O1	110.36 (19)
C3—C4—H4A	120.0	O4—Cl1—O2	109.21 (17)
C4—C5—C6	120.2 (3)	O1—Cl1—O2	109.82 (19)
C4—C5—H5A	119.9	O4—Cl1—O3	111.00 (17)
C6—C5—H5A	119.9	O1—Cl1—O3	107.96 (19)
C5—C6—C7	121.2 (3)	O2—Cl1—O3	108.46 (19)
C5—C6—H6A	119.4	O8—Cl2—O7	112 (2)
C7—C6—H6A	119.4	O8—Cl2—O5	121.0 (17)
C2—C7—C6	116.8 (3)	O7—Cl2—O5	105 (3)
C2—C7—C8	125.2 (3)	O8—Cl2—O6	104.3 (13)
C6—C7—C8	117.9 (3)	O7—Cl2—O6	110 (2)
C7—C8—N9	113.2 (2)	O5—Cl2—O6	103.4 (13)
C7—C8—H8A	108.9	O14—N11—O13	117.1 (12)
N9—C8—H8A	108.9	O14—N11—O12	121.2 (12)
C7—C8—H8B	108.9	O13—N11—O12	121.3 (12)
N9—C8—H8B	108.9

C7—C2—C3—C4	−0.3 (5)	C5—C6—C7—C2	−0.1 (4)
N1—C2—C3—C4	178.0 (3)	C5—C6—C7—C8	−177.7 (3)
C2—C3—C4—C5	−0.8 (5)	C2—C7—C8—N9	98.7 (3)
C3—C4—C5—C6	1.5 (5)	C6—C7—C8—N9	−83.9 (3)
C4—C5—C6—C7	−1.0 (5)	C7—C8—N9—C10	174.1 (3)
C3—C2—C7—C6	0.7 (4)	C8—N9—C10—C10ⁱ	−175.9 (3)
N1—C2—C7—C6	−177.5 (3)	O8—Cl2—O6—O6ⁱⁱ	−79 (5)
C3—C2—C7—C8	178.2 (3)	O7—Cl2—O6—O6ⁱⁱ	160 (6)
N1—C2—C7—C8	−0.1 (4)	O5—Cl2—O6—O6ⁱⁱ	48 (6)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···O2	0.89	2.32	2.856 (4)	118
N1—H1B···O13ⁱⁱⁱ	0.89	2.61	3.270 (13)	132
N9—H9B···O5	0.90	2.27	2.96 (3)	133
N9—H9B···O12	0.90	2.35	3.055 (15)	136
N9—H9A···O2	0.90	2.05	2.872 (4)	151
N9—H9A···O3	0.90	2.64	3.441 (4)	149
N9—H9B···O7	0.90	2.02	2.89 (5)	163
N9—H9B···O13	0.90	1.98	2.836 (13)	157
N1—H1A···O5^iv	0.89	2.04	2.91 (3)	165
N1—H1A···O12^iv	0.89	2.05	2.920 (13)	164
N1—H1B···O8ⁱⁱⁱ	0.89	1.90	2.78 (2)	170
N1—H1B···O14ⁱⁱⁱ	0.89	2.14	3.026 (11)	174
N1—H1C···O1^v	0.89	2.39	3.207 (4)	153

Symmetry codes: (iii) −x+1/2, y+1/2, −z+1/2; (iv) x−1, y, z; (v) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₆H₂₆N₄⁴⁺·2.5ClO₄⁻·1.5NO₃⁻
M_r	616.05
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	8.427 (3), 12.637 (3), 11.834 (3)
β (°)	106.97 (2)
V (Å³)	1205.4 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.41
Crystal size (mm)	0.6 × 0.4 × 0.4

Data collection
Diffractometer	Siemens P4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6392, 2125, 1757
R_int	0.057
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.119, 1.14
No. of reflections	2125
No. of parameters	218
No. of restraints	8
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.27

Computer programs: XSCANS (Siemens, 1996), SHELXTL-Plus (Sheldrick, 2008) and Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N9—H9A···O2	0.90	2.05	2.872 (4)	151.1
N9—H9B···O7	0.90	2.02	2.89 (5)	162.8
N9—H9B···O13	0.90	1.98	2.836 (13)	157.3
N1—H1A···O5ⁱ	0.89	2.04	2.91 (3)	165.2
N1—H1A···O12ⁱ	0.89	2.05	2.920 (13)	164.1
N1—H1B···O8ⁱⁱ	0.89	1.90	2.78 (2)	169.7
N1—H1B···O14ⁱⁱ	0.89	2.14	3.026 (11)	173.6
N1—H1C···O1ⁱⁱⁱ	0.89	2.39	3.207 (4)	153.0

Symmetry codes: (i) x−1, y, z; (ii) −x+1/2, y+1/2, −z+1/2; (iii) −x, −y+1, −z+1.

Acknowledgements

The authors thank FCQ-UANL for supporting this work (Project No. 03–6375-QAA-08–017)

References

Carta, D., Cao, G. & D'Angeli, C. (2003). Environ. Sci. Pollut. Res. Int. 10, 390–394. Web of Science CrossRef PubMed CAS Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CrossRef CAS IUCr Journals Google Scholar
Parra, J. B., Ania, C. O., Arenillas, A., Rubiera, F. & Pis, J. J. (2004). Appl. Surf. Sci. 238, 304–308. Web of Science CrossRef CAS Google Scholar
Pohorely, M., Vosecky, M., Hejdova, P., Puncochar, M., Skoblja, S., Staf, M., Vosta, J., Koutsky, B. & Svoboda, K. (2006). Fuel, 85, 2458–2468. Web of Science CrossRef CAS Google Scholar
Rodríguez de Barbarín, C., Bernès, S., Nájera, B., Elizondo, P. & Cerda, P. (2007). Acta Cryst. E63, o549–o550. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

N,N′-Bis(2-ammonio­benz­yl)ethane-1,2-di­ammonium–nitrate–perchlorate (1/1.5/2.5)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N,N′-Bis(2-ammoniobenzyl)ethane-1,2-diammonium–nitrate–perchlorate (1/1.5/2.5)