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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 8| August 2009| Pages o1770-o1771
doi:10.1107/S1600536809025173

Bis(3-carb­oxy­anilinum) bis­­(perchlorate) monohydrate

Lamia Bendjeddou,a* Aouatef Cherouana,a Nasreddine Hadjadj,a Slimane Dahaouib and Claude Lecomteb

aLaboratoire de Chimie Moléculaire, du Contrôle, de l'Environnement et des Mesures Physico-Chimiques, Faculté des Sciences Exactes, Département de Chimie, Université Mentouri de Constantine, 25000 Constantine, Algeria, and bCristallographie, Résonance Magnétique et Modélisation (CRM2), Université Henri Poincaré, Nancy 1, Faculté des Sciences, BP 70239, 54506 Vandoeuvre lès Nancy CEDEX, France
*Correspondence e-mail: lamiabendjeddou@yahoo.fr

(Received 12 June 2009; accepted 29 June 2009; online 4 July 2009)

In the structure of the title compound, 2C7H8NO2+·2ClO4−·H2O, the ions are connected via N—H⋯O, N—H⋯(O,O), O—H⋯O, O—H⋯(O,O) and C—H⋯O hydrogen bonds into a three-dimensional network.

Related literature

Hydrogen bonds play a crucial role in supra­molecular organization (Jeffrey, 1997[Jeffrey, G. A. (1997). An Introduction to Hydrogen Bonding. New York: Oxford University Press Inc.]; Nangia & Desiraju, 1998[Nangia, A. & Desiraju, G. R. (1998). Acta Cryst. A54, 934-944.]). Knowledge of hydrogen-bond geometries (Taylor & Kennard, 1984[Taylor, R. & Kennard, O. (1984). Acc. Chem. Res. 17, 320-326.]; Murray-Rust & Glusker, 1984[Murray-Rust, P. & Glusker, J. P. (1984). J. Am. Chem. Soc. 106, 1018-1025.]) and motif formation is vital in the modeling of protein–ligand inter­actions (Tintelnot & Andrews, 1989[Tintelnot, M. & Andrews, P. (1989). J. Comput. Aid. Mol. Des. 3, 67-84.]; Böhm & Klebe, 1996[Böhm, H.-J. & Klebe, G. (1996). Angew. Chem. Int. Ed. Engl. 35, 2588-2614.]). For hydriogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For the structures of organic salts of carboxylic acids, see: Bendjeddou et al. (2003[Bendjeddou, L., Cherouana, A., Berrah, F. & Benali-Cherif, N. (2003). Acta Cryst. E59, o574-o576.]); Cherouana et al. (2003[Cherouana, A., Bendjeddou, L. & Benali-Cherif, N. (2003). Acta Cryst. E59, o1790-o1792.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]);

[Scheme 1]

Experimental

Crystal data

  • 2C7H8NO2+·2ClO4−·H2O

  • Mr = 493.20

  • Triclinic, [P \overline 1]

  • a = 4.9170 (3) Å

  • b = 12.4030 (2) Å

  • c = 17.1030 (4) Å

  • α = 70.520 (2)°

  • β = 88.697 (3)°

  • γ = 86.166 (4)°

  • V = 981.13 (7) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.41 mm−1

  • T = 120 K

  • 0.3 × 0.03 × 0.02 mm
Data collection

  • Enraf–Nonius KappaCCD diffractometer

  • Absorption correction: none

  • 45183 measured reflections

  • 7071 independent reflections

  • 4775 reflections with I > 2σ(I)

  • Rint = 0.049
Refinement

  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.102

  • S = 0.99

  • 7071 reflections

  • 292 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.45 e Å−3

  • Δρmin = −0.57 e Å−3

Table 1
Hydrogen-bonding geometry (Å, °) and unitary motifs

D—H⋯A D—A H⋯A D⋯A D—H⋯A Motifs
N1—H1A⋯O1Wi 0.89 1.98 2.8664 (18) 171 D
N1—H1B⋯O6ii 0.89 2.11 2.9421 (19) 156 D
N1—H1B⋯O8 0.89 2.57 3.0343 (18) 114 D
N1—H1C⋯O1Wiii 0.89 1.98 2.8636 (18) 174 D
O1W—H1W⋯O1i 0.840 (14) 2.534 (19) 2.9435 (14) 111.2 (15) D
O1W—H1W⋯O3iii 0.840 (14) 2.258 (14) 3.0356 (16) 153.9 (16) D
O1W—H2W⋯O1 0.863 (14) 2.019 (15) 2.8504 (17) 161.4 (18) D
N2—H2A⋯O6 0.89 2.10 2.9336 (19) 155 D
N2—H2A⋯O7 0.89 2.57 2.9584 (18) 107 D
N2—H2B⋯O4iv 0.89 2.06 2.9382 (18) 168 D
N2—H2C⋯O3v 0.89 2.55 3.1176 (19) 122 D
N2—H2C⋯O4v 0.89 1.98 2.8683 (18) 175 D
O12—H12⋯O11vi 0.82 1.82 2.6425 (14) 178 R22(8)
O22—H22⋯O21vii 0.82 1.82 2.6428 (17) 178 R22(8)
C13—H13⋯O8 0.93 2.31 3.1193 (19) 145 D
C15—H15⋯O2i 0.93 2.43 3.3058 (19) 156 D
C23—H23⋯O4iv 0.93 2.55 3.2529 (19) 133 D
C25—H25⋯O8viii 0.93 2.49 3.384 (2) 162 D
C27—H27⋯O11vi 0.93 2.60 3.136 (2) 117 D
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) x+1, y, z; (iii) -x+1, -y+1, -z+1; (iv) -x+1, -y, -z+1; (v) -x, -y, -z+1; (vi) -x, -y+1, -z; (vii) -x+1, -y, -z; (viii) x-1, y, z. Motifs: R = ring; D = finite patterns.

Data collection: CAD-4 Software (Enraf–Nonius, 1989[Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]), PARST97 (Nardelli, 1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]), Mercury (Macrae et al., 2006[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.]) and POV-RAY (Persistence of Vision Team, 2004[Persistence of Vision Team (2004). POV-RAY. Persistence of Vision Raytracer Pty Ltd, Victoria, Australia. URL: http://www.povray.org/ .]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809025173/bq2150sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809025173/bq2150Isup2.hkl

checkCIF report


Comment top

Hydrogen bonds play a crucial role in supramolecular organization (Jeffrey, 1997; Nangia & Desiraju, 1998). Knowledge of hydrogen-bond geometries (Taylor & Kennard, 1984; Murray-Rust & Glusker, 1984) and motif formation is vital in the modeling of protein-ligand interactions (Tintelnot & Andrews, 1989; Böhm & Klebe, 1996). The supramolecular networks become especially interesting when the cation and anion can participate in hydrogen-bonding. In this regard previous studies have been concerned with organic salts of carboxylic acids (Bendjeddou et al., 2003), Cherouana et al., 2003). The asymmetric unit of (I) (Fig. 1) contains two carboxyanilinium cations (A and B), two perchlorate anion and one water molecule. A proton transfer from the perchloric acid to atom N1 and N2 of m-carboxyalinine resulted in the formation of salts.

1- Supramolecular organization:

The structure is formed by double anionic and cationic chains that extend along the b axis, giving rise to layers parallel to the plane (b, c). Chains of water molecules are sandwiched between the anionic double chains (Fig2.).

1–1- Overview.

The supramolecular architecture is generated by the nineteen independent interactions of the Table 1. Three types of intermolecular interactions are present in the structure, including O—H···O, N—H···O and C—H···O hydrogen bonds. The presence of water molecule in the structure results in the presence of additional hydrogen bonds. The construction of graphs-set of the twenty hydrogen bonds in this compound has led to a first-level graph set noted: N1 = R22(8)R22(8) (Bernstein et al., 1995) (Table 1.).

1–2- The O—H···O hydrogen-bonded network

The carboxylic acid groups at the opposite end of the carboxyanilinium cations forms a centrosymmetric hydrogen-bonded dimers with its counterpart in a cation from an adjacent ribbon and are centered at (0 1/2 0) and (1/2 0 0) respectively for cation A and cation B (Fig. 3). These interactions lead to the graph-set motif R22(8), which is a characteristic feature found in most salts of 3- and 4-aminobenzoic acid (Cambridge Structural Database; Allen, 2002).

The water molecule, bridges the anionic perchlorate via the O—H···O hydrogen bonds. The centrosymmetric hydrogen-bonded rings formed by two water molecules and two Cl(1)O4- anions can be described by the graph-set R44(12) and R24(8). The aggregation of this two ring motifs results in an overall one-dimensional hydrogen-bonded chain structure along the [100] direction (Fig. 4).

1–3- The N—H···O hydrogen-bonded network

In the first cationic (A) entity, all ammonium H atoms are involved in hydrogen bonds with the perchlorate (Cl(2) O4-) anion and water molecule. Two of these interactions link the anions and cations in an alternating fashion into extended chains along the [100] direction, which can be described by the graph-set C22(4). The two other interactions are in a crosslink from an adjacent chain C22(4). The combination of these two chain motifs generates noncentrosymmetric fused rings which can be described by the graph-set motif R34(10).

In the second cationic (B) entitie, all ammonium H atoms are involved in hydrogen bonds, with the two different perchlorate ion, so forming an alternating noncentrosymmetric rings a long [100] direction which can be described by the graph-set R34(10). Only one H atom (H2C) is involved in bifurcated hydrogen bonds with O(3) and O(4) perchlorate atoms, to form a four-membered hydrogen bonded ring R21(4). The junction betwen this two different cations (A and B) entities are assured by the perchlorate (Cl(2) O4-) anion via N1—H1B···O6, N1—H1B···O8, N2—H2A···O6, N2—H2A···O7 hydrogen bonds, so generete R32(6) rings along [100] direction (Fig. 5)

1–4- The C—H···O hydrogen-bonded network:

The junction between the cationic entity is consolidated by five weak independent C—H···O hydrogen bonds via the perchlorate anions, forming an alternating of R46(22) and R56(30)centrosymmetric Rings a long b axis (Fig. 6).

Related literature top

Hydrogen bonds play a crucial role in supramolecular organization (Jeffrey, 1997; Nangia & Desiraju, 1998). Knowledge of hydrogen-bond geometries (Taylor & Kennard, 1984; Murray-Rust & Glusker, 1984) and motif formation is vital in the modeling of protein–ligand interactions (Tintelnot & Andrews, 1989; Böhm & Klebe, 1996). For hydriogen-bond motifs, see: Bernstein et al. (1995). For the structures of organic salts of carboxylic acids, see: Bendjeddou et al. (2003); Cherouana et al. (2003). For a description of the Cambridge Structural Database, see: Allen (2002);

Experimental top

m-carboxyanilinium acid and perchloric acid were mixed in a 2:2 stoichiometric ratio and dissolved in water. Crystal were obtained by slow evaporation.

Refinement top

H atoms were positioned geometrically and refined in the riding-model approximation, with C—H = 0.97 Å, N—H = 0.89 Å, O—H = 0.82 Å, and with Uiso(H) = 1.2Ueq(C, N) or 1.5Ueq(O). The H atoms of the water molecule were located in a difference Fourier map and reined as riding, with O—H = 0.85 Å and Uiso(H) = 1.5Ueq(O).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999), PARST97 (Nardelli, 1995), Mercury (Macrae et al., 2006) and POVRay (Persistence of Vision Team, 2004).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of (I), showing the crystallographic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as spheres of arbitrary radii.
[Figure 2] Fig. 2. A packing diagram for the title compound, viewed along the a axis, showing the mixture layers.
[Figure 3] Fig. 3. Part of the crystal structure, showing the formation of dimers A and B via O—H···O hydrogen bonds.
[Figure 4] Fig. 4. A view of the two-dimensional O—H···O hydrogen-bonded network paralel to the (100) plane of (I), showing the aggregation of R44(12) and R24(8) hydrogen-bonding motifs. Atoms marked with an ampersand (&), an at sign (@), a hash symbol (#) or a dollar sign ($) are at the symmetry positions (1 + x, y, z), (-1 + x, y, z), (1 - x, 1 - y, 1 - z), (2 - x, 1 - y, 1 - z), respectively.
[Figure 5] Fig. 5. Part of the crystal structure, showing the aggregation of C22(4) R34(10) and R32(6) motifs via N—H···O hydrogen bonds. Atoms marked with an ampersand (&), an at sign (@), a hash symbol (#), dollar sign ($), percent sign (%), or a star sign (*) are at the symmetry positions (1 - x, 1 - y, 1 - z), (-1 + x, y, z), (1 - x, y, 1 - z), (-x, -y, 1 - z), (1 + x, y, z), (2 - x, 1 - y, 1 - z), respectively.
[Figure 6] Fig. 6. A view of part of the crystal structure of (I), showing the formation of R46(22) and R56(30) rings. Atoms marked with an ampersand (&), a hash symbol (#), dollar sign ($), percent sign (%), or a star sign (*) are at the symmetry positions (2 - x, -y, 1 - z), (-x, 1 - y, -z), (1 - x, 1 - y, -z), (1 + x, y, z), (2 - x, 1 - y, 1 - z), respectively.
Bis(3-carboxyanilinum) bis(perchlorate) monohydrate top
Crystal data top
2C7H8NO2+·2ClO4−·H2OZ = 2
Mr = 493.20F(000) = 508
Triclinic, P1Dx = 1.669 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 4.9170 (3) ÅCell parameters from 7071 reflections
b = 12.4030 (2) Åθ = 3.3–32.6°
c = 17.1030 (4) ŵ = 0.41 mm−1
α = 70.520 (2)°T = 120 K
β = 88.697 (3)°Needle, brown
γ = 86.166 (4)°0.3 × 0.03 × 0.02 mm
V = 981.13 (7) Å3
Data collection top
Enraf–Nonius KappaCCD
diffractometer		4775 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.049
Graphite monochromatorθmax = 32.6°, θmin = 3.3°
ω scansh = 0→7
45183 measured reflectionsk = −18→18
7071 independent reflectionsl = −25→25
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.039 w = 1/[σ2(Fo2) + (0.0526P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.102(Δ/σ)max = 0.021
S = 0.99Δρmax = 0.45 e Å−3
7071 reflectionsΔρmin = −0.57 e Å−3
292 parameters
Crystal data top
2C7H8NO2+·2ClO4−·H2Oγ = 86.166 (4)°
Mr = 493.20V = 981.13 (7) Å3
Triclinic, P1Z = 2
a = 4.9170 (3) ÅMo Kα radiation
b = 12.4030 (2) ŵ = 0.41 mm−1
c = 17.1030 (4) ÅT = 120 K
α = 70.520 (2)°0.3 × 0.03 × 0.02 mm
β = 88.697 (3)°
Data collection top
Enraf–Nonius KappaCCD
diffractometer		4775 reflections with I > 2σ(I)
45183 measured reflectionsRint = 0.049
7071 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.102H atoms treated by a mixture of independent and constrained refinement
S = 0.99Δρmax = 0.45 e Å−3
7071 reflectionsΔρmin = −0.57 e Å−3
292 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O110.2368 (2)0.58575 (9)0.00162 (6)0.0167 (3)
O120.1451 (2)0.42214 (9)0.10223 (6)0.0176 (3)
N10.6845 (3)0.40582 (11)0.35093 (7)0.0142 (4)
C110.2756 (3)0.51695 (13)0.07149 (9)0.0136 (4)
C120.4736 (3)0.53492 (13)0.12947 (9)0.0131 (4)
C130.4963 (3)0.45953 (13)0.21027 (9)0.0132 (4)
C140.6728 (3)0.48155 (13)0.26416 (9)0.0127 (4)
C150.8297 (3)0.57585 (13)0.23929 (9)0.0154 (4)
C160.8057 (3)0.65062 (13)0.15814 (9)0.0172 (5)
C170.6279 (3)0.63090 (13)0.10338 (9)0.0154 (4)
O210.2424 (2)0.08889 (10)−0.00149 (6)0.0195 (3)
O220.3663 (3)−0.06863 (10)0.10513 (7)0.0231 (4)
N2−0.2091 (3)−0.04135 (11)0.34838 (7)0.0132 (3)
C210.2141 (3)0.02587 (13)0.07045 (9)0.0162 (4)
C220.0034 (3)0.05317 (13)0.12572 (9)0.0146 (4)
C23−0.0102 (3)−0.01242 (13)0.20967 (9)0.0137 (4)
C24−0.1986 (3)0.02235 (13)0.25877 (9)0.0130 (4)
C25−0.3762 (3)0.11787 (14)0.22733 (9)0.0171 (4)
C26−0.3649 (3)0.18137 (14)0.14357 (10)0.0193 (5)
C27−0.1724 (3)0.14958 (14)0.09290 (9)0.0173 (4)
Cl10.58901 (7)0.29103 (3)0.61432 (2)0.0133 (1)
O10.7010 (2)0.36508 (9)0.53790 (6)0.0191 (3)
O20.6783 (2)0.32216 (11)0.68248 (7)0.0237 (4)
O30.2956 (2)0.30140 (10)0.60921 (7)0.0208 (3)
O40.6805 (2)0.17339 (9)0.62552 (7)0.0201 (3)
Cl20.14254 (7)0.15743 (3)0.40892 (2)0.0128 (1)
O50.2017 (3)0.17301 (10)0.48568 (7)0.0244 (4)
O6−0.1515 (2)0.15994 (10)0.39893 (7)0.0220 (3)
O70.2591 (2)0.04883 (9)0.40697 (7)0.0207 (3)
O80.2470 (2)0.24934 (9)0.34137 (7)0.0205 (3)
O1W0.8260 (2)0.56613 (10)0.57195 (7)0.0156 (3)
H1A0.826770.421110.375830.0212*
H1B0.701850.333150.352720.0212*
H1C0.531900.417280.376840.0212*
H120.026480.421040.069610.0263*
H130.394320.395210.227900.0159*
H150.948840.588930.276150.0185*
H160.909760.714300.140510.0206*
H170.611450.681590.049350.0185*
H2A−0.225910.007890.376220.0198*
H2B−0.05642−0.085630.363800.0198*
H2C−0.35139−0.084810.359260.0198*
H220.48980−0.074140.073380.0345*
H230.10478−0.077830.231860.0165*
H25−0.501540.139230.261860.0205*
H26−0.485330.244940.121310.0232*
H27−0.161750.193020.037000.0208*
H1W0.826 (4)0.6178 (12)0.5253 (8)0.037 (6)*
H2W0.827 (4)0.5046 (10)0.5589 (11)0.039 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O110.0196 (6)0.0163 (6)0.0123 (5)−0.0034 (4)−0.0031 (4)−0.0017 (4)
O120.0198 (6)0.0159 (6)0.0155 (5)−0.0059 (5)−0.0060 (4)−0.0020 (4)
N10.0141 (6)0.0172 (7)0.0120 (6)−0.0003 (5)−0.0017 (5)−0.0059 (5)
C110.0135 (7)0.0131 (7)0.0144 (7)−0.0001 (6)0.0004 (6)−0.0049 (6)
C120.0130 (7)0.0140 (7)0.0124 (7)−0.0006 (6)−0.0006 (5)−0.0044 (6)
C130.0129 (7)0.0123 (7)0.0148 (7)−0.0008 (6)0.0000 (5)−0.0049 (6)
C140.0131 (7)0.0134 (7)0.0114 (7)0.0002 (6)0.0009 (5)−0.0040 (5)
C150.0144 (7)0.0173 (8)0.0165 (7)−0.0013 (6)−0.0018 (6)−0.0080 (6)
C160.0173 (8)0.0144 (8)0.0200 (8)−0.0043 (6)0.0009 (6)−0.0054 (6)
C170.0161 (8)0.0147 (7)0.0134 (7)−0.0008 (6)−0.0003 (6)−0.0020 (6)
O210.0220 (6)0.0200 (6)0.0128 (5)0.0032 (5)0.0050 (4)−0.0019 (4)
O220.0253 (7)0.0218 (6)0.0164 (6)0.0091 (5)0.0070 (5)−0.0013 (5)
N20.0145 (6)0.0139 (6)0.0115 (6)−0.0022 (5)0.0010 (5)−0.0044 (5)
C210.0172 (8)0.0159 (8)0.0155 (7)0.0011 (6)0.0004 (6)−0.0058 (6)
C220.0168 (7)0.0145 (7)0.0122 (7)−0.0008 (6)0.0022 (6)−0.0043 (6)
C230.0138 (7)0.0128 (7)0.0130 (7)0.0003 (6)−0.0009 (5)−0.0024 (6)
C240.0147 (7)0.0125 (7)0.0112 (7)−0.0032 (6)0.0006 (5)−0.0029 (5)
C250.0174 (8)0.0177 (8)0.0163 (7)0.0004 (6)0.0044 (6)−0.0063 (6)
C260.0216 (8)0.0160 (8)0.0167 (8)0.0064 (6)0.0009 (6)−0.0020 (6)
C270.0214 (8)0.0157 (8)0.0119 (7)0.0015 (6)0.0021 (6)−0.0012 (6)
Cl10.0122 (2)0.0142 (2)0.0143 (2)−0.0018 (1)−0.0003 (1)−0.0057 (1)
O10.0220 (6)0.0172 (6)0.0156 (5)−0.0045 (5)0.0030 (4)−0.0018 (4)
O20.0246 (6)0.0332 (7)0.0196 (6)−0.0101 (5)−0.0005 (5)−0.0156 (5)
O30.0109 (5)0.0266 (7)0.0263 (6)0.0002 (5)0.0003 (4)−0.0109 (5)
O40.0175 (6)0.0120 (5)0.0289 (6)0.0014 (4)−0.0016 (5)−0.0048 (5)
Cl20.0145 (2)0.0117 (2)0.0122 (2)−0.0018 (1)0.0007 (1)−0.0039 (1)
O50.0355 (7)0.0256 (7)0.0138 (5)−0.0047 (5)−0.0032 (5)−0.0081 (5)
O60.0127 (5)0.0219 (6)0.0340 (7)−0.0021 (5)0.0002 (5)−0.0127 (5)
O70.0203 (6)0.0123 (5)0.0302 (6)0.0016 (4)0.0008 (5)−0.0087 (5)
O80.0284 (7)0.0152 (6)0.0155 (5)−0.0072 (5)0.0062 (5)−0.0013 (4)
O1W0.0175 (6)0.0136 (5)0.0145 (5)−0.0022 (4)−0.0012 (4)−0.0028 (4)
Geometric parameters (Å, º) top
Cl1—O21.4307 (11)N1—H1C0.89
Cl1—O31.4418 (11)C22—C271.389 (2)
Cl1—O11.4454 (11)C22—C231.397 (2)
Cl1—O41.4484 (11)C22—C211.484 (2)
Cl2—O51.4282 (11)C24—C231.379 (2)
Cl2—O71.4386 (11)C24—C251.383 (2)
Cl2—O81.4390 (11)C14—C131.3833 (19)
Cl2—O61.4568 (11)C14—C151.385 (2)
O12—C111.3208 (17)C12—C131.388 (2)
O12—H120.82C12—C171.394 (2)
O1W—H2W0.863 (9)C12—C111.484 (2)
O1W—H1W0.840 (9)C27—C261.394 (2)
O11—C111.2252 (17)C27—H270.93
O22—C211.3135 (19)C16—C171.386 (2)
O22—H220.82C16—C151.391 (2)
O21—C211.2286 (18)C16—H160.93
N2—C241.4732 (18)C23—H230.93
N2—H2A0.89C15—H150.93
N2—H2B0.89C25—C261.388 (2)
N2—H2C0.89C25—H250.93
N1—C141.4679 (18)C17—H170.93
N1—H1A0.89C13—H130.93
N1—H1B0.89C26—H260.93
O2—Cl1—O3110.41 (7)C15—C14—N1119.21 (13)
O2—Cl1—O1109.66 (7)C13—C12—C17120.21 (13)
O3—Cl1—O1109.24 (7)C13—C12—C11120.24 (13)
O2—Cl1—O4109.82 (7)C17—C12—C11119.48 (13)
O3—Cl1—O4108.57 (7)O11—C11—O12123.69 (13)
O1—Cl1—O4109.11 (7)O11—C11—C12122.07 (13)
O5—Cl2—O7110.85 (7)O12—C11—C12114.24 (13)
O5—Cl2—O8109.49 (7)O21—C21—O22123.78 (14)
O7—Cl2—O8110.20 (7)O21—C21—C22121.54 (14)
O5—Cl2—O6109.62 (7)O22—C21—C22114.67 (13)
O7—Cl2—O6108.29 (7)C22—C27—C26120.12 (14)
O8—Cl2—O6108.34 (7)C22—C27—H27119.9
C11—O12—H12109.5C26—C27—H27119.9
H2W—O1W—H1W102.4 (15)C17—C16—C15120.47 (14)
C21—O22—H22109.5C17—C16—H16119.8
C24—N2—H2A109.5C15—C16—H16119.8
C24—N2—H2B109.5C24—C23—C22118.26 (14)
H2A—N2—H2B109.5C24—C23—H23120.9
C24—N2—H2C109.5C22—C23—H23120.9
H2A—N2—H2C109.5C14—C15—C16118.76 (14)
H2B—N2—H2C109.5C14—C15—H15120.6
C14—N1—H1A109.5C16—C15—H15120.6
C14—N1—H1B109.5C24—C25—C26119.11 (14)
H1A—N1—H1B109.5C24—C25—H25120.4
C14—N1—H1C109.5C26—C25—H25120.4
H1A—N1—H1C109.5C16—C17—C12119.84 (14)
H1B—N1—H1C109.5C16—C17—H17120.1
C27—C22—C23120.41 (14)C12—C17—H17120.1
C27—C22—C21118.25 (13)C14—C13—C12118.99 (13)
C23—C22—C21121.26 (14)C14—C13—H13120.5
C23—C24—C25122.28 (14)C12—C13—H13120.5
C23—C24—N2119.74 (13)C25—C26—C27119.79 (15)
C25—C24—N2117.96 (13)C25—C26—H26120.1
C13—C14—C15121.73 (14)C27—C26—H26120.1
C13—C14—N1119.00 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1Wi0.89001.98002.8664 (18)171.00
N1—H1B···O6ii0.89002.11002.9421 (19)156.00
N1—H1B···O80.89002.57003.0343 (18)114.00
N1—H1C···O1Wiii0.89001.98002.8636 (18)174.00
O1W—H1W···O1i0.840 (14)2.534 (19)2.9435 (14)111.2 (15)
O1W—H1W···O3iii0.840 (14)2.258 (14)3.0356 (16)153.9 (16)
N2—H2A···O60.89002.10002.9336 (19)155.00
N2—H2A···O70.89002.57002.9584 (18)107.00
N2—H2B···O4iv0.89002.06002.9382 (18)168.00
N2—H2C···O3v0.89002.55003.1176 (19)122.00
N2—H2C···O4v0.89001.98002.8683 (18)175.00
O1W—H2W···O10.863 (14)2.019 (15)2.8504 (17)161.4 (18)
O12—H12···O11vi0.82001.82002.6425 (14)178.00
O22—H22···O21vii0.82001.82002.6428 (17)178.00
C13—H13···O80.93002.31003.1193 (19)145.00
C15—H15···O2i0.93002.43003.3058 (19)156.00
C23—H23···O4iv0.93002.55003.2529 (19)133.00
C25—H25···O8viii0.93002.49003.384 (2)162.00
C27—H27···O11vi0.93002.6023.136 (2)117.05
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x+1, y, z; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y, −z+1; (v) −x, −y, −z+1; (vi) −x, −y+1, −z; (vii) −x+1, −y, −z; (viii) x−1, y, z.

Experimental details

Crystal data
Chemical formula2C7H8NO2+·2ClO4−·H2O
Mr493.20
Crystal system, space groupTriclinic, P1
Temperature (K)120
a, b, c (Å)4.9170 (3), 12.4030 (2), 17.1030 (4)
α, β, γ (°)70.520 (2), 88.697 (3), 86.166 (4)
V (Å3)981.13 (7)
Z2
Radiation typeMo Kα
µ (mm−1)0.41
Crystal size (mm)0.3 × 0.03 × 0.02
Data collection
DiffractometerEnraf–Nonius KappaCCD
diffractometer
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		45183, 7071, 4775
Rint0.049
(sin θ/λ)max (Å−1)0.757
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.102, 0.99
No. of reflections7071
No. of parameters292
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.45, −0.57

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999), PARST97 (Nardelli, 1995), Mercury (Macrae et al., 2006) and POVRay (Persistence of Vision Team, 2004).

Hydrogen-bonding geometry (Å, °) and unitary motifs top
D—H···AD—AH···AD···AD—H···AMotifs
N1—H1A···O1Wi0.891.982.8664 (18)171D
N1—H1B···O6ii0.892.112.9421 (19)156D
N1—H1B···O80.892.573.0343 (18)114D
N1—H1C···O1Wiii0.891.982.8636 (18)174D
O1W—H1W···O1i0.840 (14)2.534 (19)2.9435 (14)111.2 (15)D
O1W—H1W···O3iii0.840 (14)2.258 (14)3.0356 (16)153.9 (16)D
N2—H2A···O60.892.102.9336 (19)155D
N2—H2A···O70.892.572.9584 (18)107D
N2—H2B···O4iv0.892.062.9382 (18)168D
N2—H2C···O3v0.892.553.1176 (19)122D
N2—H2C···O4v0.891.982.8683 (18)175D
O1W—H2W···O10.863 (14)2.019 (15)2.8504 (17)161.4 (18)D
O12—H12···O11vi0.821.822.6425 (14)178R22(8)
O22—H22···O21vii0.821.822.6428 (17)178R22(8)
C13—H13···O80.932.313.1193 (19)145D
C15—H15···O2i0.932.433.3058 (19)156D
C23—H23···O4iv0.932.553.2529 (19)133D
C25—H25···O8viii0.932.493.384 (2)162D
C27—H27···O11vi0.932.603.136 (2)117D
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) x+1, y, z; (iii) -x+1, -y+1, -z+1; (iv) -x+1, -y, -z+1; (v) -x, -y, -z+1; (vi) -x, -y+1, -z; (vii) -x+1, -y, -z; (viii) x-1, y, z.
 

Acknowledgements

Technical support (X-ray measurements at SCDRX) from Université Henry Poincaré, Nancy 1, is gratefully acknowledged.

References

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ISSN: 2056-9890
Volume 65| Part 8| August 2009| Pages o1770-o1771
doi:10.1107/S1600536809025173
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