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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 66| Part 12| December 2010| Page o3169
https://doi.org/10.1107/S1600536810046106

Pyridine-2-carboximidamidate chloride monohydrate

Qifan Chen,a Huidong Zhang,a Fang Zhangb and Fei Liub*

aExperiment Center, Eastern Liaoning University, No. 325 Wenhua Road, Yuanbao District, Dandong City, Liaoning Province 118003, People's Republic of China, and bCollege of Chemical Engineering & Materials, Eastern Liaoning University, No. 325 Wenhua Road, Yuanbao District, Dandong City, Liaoning Province 118003, People's Republic of China
*Correspondence e-mail: berylliu8090@sina.com

(Received 26 October 2010; accepted 9 November 2010; online 13 November 2010)

The title compound, C6H8N3+·Cl−·H2O, crystallizes with three formula units in the asymmetric unit. The cations are non-planar with the –C(NH2)2 groups twisted out of the ring planes. Each pyridine carboximidamidate cation is linked to another cation through N—H⋯N hydrogen bonds, to chloride ions by N—H⋯Cl hydrogen bonds, and to water mol­ecules by N—H⋯O hydrogen bonds. Water mol­ecules and chloride ions are also linked together via O—H⋯Cl hydrogen bonds. In the crystal, all these inter­molecular inter­actions result in a three-dimensional network.

Related literature

For related structures, see: Guo et al. (2005[Guo, J., Wong, W.-K. & Wong, W.-Y. (2005). Polyhedron, 24, 927-939.]); Fan et al. (2009[Fan, P., Wang, L. & Zhang, H. (2009). Acta Cryst. E65, o2408.]); Góker et al. (2005[Góker, H., Ózden, S., Yildiz, S. & Boykin, D. W. (2005). Eur. J. Med. Chem. 40, 1062-1069.]); Walther et al. (2006[Walther, M., Wermann, H., Lutsche, M., Gúnther, W., Górls, H. & Anders, E. (2006). J. Org. Chem. 71, 1399-1406.]).

[Scheme 1]

Experimental

Crystal data

  • C6H8N3+·Cl−·H2O

  • Mr = 175.62

  • Triclinic, [P \overline 1]

  • a = 7.2570 (15) Å

  • b = 11.146 (2) Å

  • c = 16.862 (3) Å

  • α = 79.24 (3)°

  • β = 82.14 (3)°

  • γ = 78.34 (3)°

  • V = 1305.3 (5) Å3

  • Z = 6

  • Mo Kα radiation

  • μ = 0.39 mm−1

  • T = 293 K

  • 0.25 × 0.24 × 0.22 mm
Data collection

  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.909, Tmax = 0.918

  • 12872 measured reflections

  • 5919 independent reflections

  • 4550 reflections with I > 2σ(I)

  • Rint = 0.024
Refinement

  • R[F2 > 2σ(F2)] = 0.035

  • wR(F2) = 0.117

  • S = 1.11

  • 5919 reflections

  • 418 parameters

  • All H-atom parameters refined

  • Δρmax = 0.23 e Å−3

  • Δρmin = −0.26 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N23—H23B⋯O1i 0.87 (2) 1.97 (2) 2.829 (2) 173 (2)
N22—H22B⋯Cl1 0.89 (3) 2.31 (3) 3.187 (2) 169 (2)
N12—H12B⋯Cl3ii 0.91 (2) 2.35 (2) 3.2522 (19) 170.2 (18)
O1—H1B⋯Cl3 0.80 (3) 2.37 (3) 3.163 (2) 169 (2)
N2—H2A⋯Cl2iii 0.85 (3) 2.49 (3) 3.326 (2) 167 (2)
O1—H10⋯Cl2iv 0.98 (4) 2.22 (4) 3.1902 (19) 173 (3)
N3—H3A⋯O2 0.87 (2) 1.94 (2) 2.808 (2) 174.9 (19)
N2—H2B⋯Cl1 0.96 (2) 2.32 (2) 3.2754 (17) 170.9 (17)
N12—H12A⋯Cl3v 0.89 (2) 2.43 (2) 3.313 (2) 171 (2)
N23—H23A⋯Cl3vi 0.87 (2) 2.50 (2) 3.324 (2) 158 (2)
N13—H13B⋯O3ii 0.92 (2) 1.97 (2) 2.883 (2) 178 (2)
N22—H22A⋯Cl2iii 0.91 (2) 2.43 (3) 3.3194 (18) 168 (2)
N13—H13A⋯Cl1 0.91 (2) 2.48 (2) 3.335 (2) 156.9 (19)
O3—H03B⋯Cl2iv 0.84 (4) 2.45 (4) 3.286 (2) 174 (3)
O2—H0B⋯Cl1 0.85 (3) 2.28 (3) 3.1171 (18) 172 (2)
O2—H0A⋯Cl2 0.79 (3) 2.40 (3) 3.1833 (18) 175 (3)
O3—H03A⋯Cl3 0.94 (4) 2.25 (4) 3.1586 (18) 164 (3)
Symmetry codes: (i) x-1, y, z; (ii) x, y-1, z; (iii) -x, -y+1, -z; (iv) -x+1, -y+1, -z; (v) -x+1, -y+1, -z+1; (vi) -x, -y+1, -z+1.

Data collection: RAPID-AUTO (Rigaku, 1998)[Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]; cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: DIAMOND (Brandenburg, 1999[Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]) and SHELXP97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810046106/zq2070sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810046106/zq2070Isup2.hkl

checkCIF report


Comment top

The pyridinecarboximidamidate derivatives have attracted a great attention due to their very potent antibacterial activities, interesting biological properties and applications in coordination chemistry, but a few samples have been reported (Guo et al., 2005; Góker et al., 2005; Walther et al., 2006; Fan et al., 2009). Here we report the structure of title compound C6H8N3+.Cl-.H2O. The title compound is an organic salt and crystallizes with three formula units in the asymmetric unit (Fig. 1). The molecules are nonplanar with the C(NH2)2 groups twisted out of the ring planes. The bond lengths and angles exhibit normal values and are comparable with those in the related structures (Guo et al., 2005; Fan et al., 2009).

In the crystal structure, pyridine carboximidamidate cations adopt three different connecting types (Fig. 2). Each pyridine carboximidamidate cation is linked to another cation through N—H···N hydrogen bonds, to chloride ions by N—H···Cl hydrogen bonds, and to water molecules by N—H···O hydrogen bonds. Water molecules and chloride ions are also linked together via O—H···Cl hydrogen bonds (Table 1). In the crystal structure, all these intermolecular interactions result in a three-dimensional network (Fig. 3).

Related literature top

For related structures, see: Guo et al. (2005); Fan et al. (2009); Góker et al. (2005); Walther et al. (2006).

Experimental top

To a solution of sodium methoxide (5.15 mmol) in methanol (50 mL) was added 2-cyanopyridine (5.2 g, 4.99 mmol). The mixture was stirred at room temperature for 4 h. Then ammonium chloride (2.9 g, 5.42 mmol) was slowly added to the resulting solution and the mixture was stirred at room temperature for 68 h. The resulting suspension was filtered and the solvent was removed from the filtrate under reduced pressure. Purification by wash with ethyl ether gave 2-amidinopyridine hydrochloride (5.62 g, 92%) as an off-white solid. Colorless crystals were formed after several days.

Refinement top

The H atoms were initially found in a difference Fourier map and their coordinates were refined freely.

Structure description top

The pyridinecarboximidamidate derivatives have attracted a great attention due to their very potent antibacterial activities, interesting biological properties and applications in coordination chemistry, but a few samples have been reported (Guo et al., 2005; Góker et al., 2005; Walther et al., 2006; Fan et al., 2009). Here we report the structure of title compound C6H8N3+.Cl-.H2O. The title compound is an organic salt and crystallizes with three formula units in the asymmetric unit (Fig. 1). The molecules are nonplanar with the C(NH2)2 groups twisted out of the ring planes. The bond lengths and angles exhibit normal values and are comparable with those in the related structures (Guo et al., 2005; Fan et al., 2009).

In the crystal structure, pyridine carboximidamidate cations adopt three different connecting types (Fig. 2). Each pyridine carboximidamidate cation is linked to another cation through N—H···N hydrogen bonds, to chloride ions by N—H···Cl hydrogen bonds, and to water molecules by N—H···O hydrogen bonds. Water molecules and chloride ions are also linked together via O—H···Cl hydrogen bonds (Table 1). In the crystal structure, all these intermolecular interactions result in a three-dimensional network (Fig. 3).

For related structures, see: Guo et al. (2005); Fan et al. (2009); Góker et al. (2005); Walther et al. (2006).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: RAPID-AUTO (Rigaku, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999) and SHELXP97 (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound showing 30% probability displacement ellipsoids for non-H atoms.
[Figure 2] Fig. 2. View of the hydrogen bonding interactions in the title compound.
[Figure 3] Fig. 3. Crystal packing of the title compound.
Pyridine-2-carboximidamidate chloride monohydrate top
Crystal data top
C6H8N3+·Cl−·H2OZ = 6
Mr = 175.62F(000) = 552
Triclinic, P1Dx = 1.340 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.2570 (15) ÅCell parameters from 9445 reflections
b = 11.146 (2) Åθ = 3.0–27.4°
c = 16.862 (3) ŵ = 0.39 mm−1
α = 79.24 (3)°T = 293 K
β = 82.14 (3)°Block, colourless
γ = 78.34 (3)°0.25 × 0.24 × 0.22 mm
V = 1305.3 (5) Å3
Data collection top
Rigaku R-AXIS RAPID
diffractometer		5919 independent reflections
Radiation source: fine-focus sealed tube4550 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
Detector resolution: 10 pixels mm-1θmax = 27.5°, θmin = 3.0°
ω scansh = −9→9
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		k = −14→14
Tmin = 0.909, Tmax = 0.918l = −21→21
12872 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117All H-atom parameters refined
S = 1.11 w = 1/[σ2(Fo2) + (0.0684P)2]
where P = (Fo2 + 2Fc2)/3
5919 reflections(Δ/σ)max = 0.001
418 parametersΔρmax = 0.23 e Å−3
0 restraintsΔρmin = −0.26 e Å−3
Crystal data top
C6H8N3+·Cl−·H2Oγ = 78.34 (3)°
Mr = 175.62V = 1305.3 (5) Å3
Triclinic, P1Z = 6
a = 7.2570 (15) ÅMo Kα radiation
b = 11.146 (2) ŵ = 0.39 mm−1
c = 16.862 (3) ÅT = 293 K
α = 79.24 (3)°0.25 × 0.24 × 0.22 mm
β = 82.14 (3)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer		5919 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		4550 reflections with I > 2σ(I)
Tmin = 0.909, Tmax = 0.918Rint = 0.024
12872 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0350 restraints
wR(F2) = 0.117All H-atom parameters refined
S = 1.11Δρmax = 0.23 e Å−3
5919 reflectionsΔρmin = −0.26 e Å−3
418 parameters
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
xyzUiso*/Ueq
Cl10.17320 (7)0.30230 (4)0.10288 (2)0.04346 (13)
O10.7888 (3)0.60439 (14)0.40146 (10)0.0647 (4)
H1B0.690 (4)0.647 (3)0.4141 (15)0.073 (8)*
H100.821 (5)0.635 (3)0.344 (2)0.120 (11)*
N10.3062 (2)0.86483 (13)−0.07194 (8)0.0432 (3)
C10.3052 (3)0.98536 (18)−0.07462 (13)0.0540 (5)
H10.336 (4)1.031 (2)−0.1243 (15)0.078 (7)*
Cl20.13596 (7)0.30724 (4)−0.21061 (3)0.04888 (14)
O20.3482 (2)0.37193 (13)−0.07519 (9)0.0530 (4)
H0B0.305 (4)0.345 (2)−0.0273 (16)0.077 (8)*
H0A0.297 (4)0.351 (2)−0.1073 (17)0.075 (8)*
N20.1754 (2)0.60101 (14)0.06004 (10)0.0429 (3)
H2A0.111 (4)0.629 (2)0.1009 (15)0.071 (7)*
H2B0.180 (3)0.513 (2)0.0663 (12)0.053 (6)*
C20.2604 (3)1.04352 (17)−0.00802 (14)0.0561 (5)
H20.261 (3)1.131 (2)−0.0152 (12)0.055 (6)*
Cl30.43514 (7)0.80296 (4)0.45146 (3)0.05099 (14)
O30.4557 (3)0.86529 (14)0.26022 (10)0.0627 (4)
H03B0.561 (5)0.826 (3)0.2445 (19)0.102 (11)*
H03A0.448 (5)0.831 (3)0.316 (2)0.121 (12)*
N30.3540 (2)0.61884 (14)−0.06282 (9)0.0426 (3)
H3B0.410 (3)0.669 (2)−0.1007 (13)0.054 (6)*
H3A0.350 (3)0.544 (2)−0.0696 (12)0.051 (5)*
C30.2174 (3)0.97567 (18)0.06587 (13)0.0564 (5)
H30.189 (3)1.014 (2)0.1127 (14)0.070 (7)*
C40.2181 (3)0.85015 (18)0.07107 (11)0.0478 (4)
H40.192 (3)0.800 (2)0.1214 (14)0.067 (7)*
C50.2600 (2)0.80020 (14)0.00027 (9)0.0343 (3)
C60.2627 (2)0.66679 (14)−0.00077 (9)0.0338 (3)
N110.4303 (2)0.37190 (13)0.25233 (9)0.0428 (3)
C110.4055 (3)0.49449 (19)0.24780 (13)0.0540 (5)
H110.446 (3)0.542 (2)0.2001 (13)0.058 (6)*
N120.4363 (3)0.09814 (16)0.39452 (10)0.0502 (4)
H12B0.440 (3)0.014 (2)0.4040 (13)0.055 (6)*
H12A0.456 (3)0.128 (2)0.4371 (15)0.065 (7)*
C120.3223 (3)0.55573 (19)0.31194 (14)0.0604 (5)
H120.311 (4)0.648 (2)0.3024 (15)0.081 (8)*
N130.3872 (2)0.12940 (15)0.25963 (10)0.0447 (3)
H13B0.413 (3)0.045 (2)0.2600 (13)0.059 (6)*
H13A0.360 (3)0.187 (2)0.2153 (13)0.060 (6)*
C130.2613 (3)0.4879 (2)0.38308 (14)0.0599 (5)
H130.207 (4)0.528 (2)0.4224 (16)0.078 (8)*
C140.2851 (3)0.36072 (18)0.38966 (12)0.0477 (4)
H140.241 (3)0.3113 (19)0.4350 (12)0.048 (5)*
C150.3718 (2)0.30783 (15)0.32274 (10)0.0368 (3)
C160.4002 (2)0.17137 (16)0.32577 (10)0.0384 (4)
N21−0.0617 (2)0.10605 (13)0.39607 (8)0.0441 (3)
C21−0.0357 (3)−0.01675 (19)0.40054 (13)0.0563 (5)
H21−0.005 (3)−0.059 (2)0.4527 (13)0.062 (6)*
N22−0.0909 (2)0.38620 (15)0.25737 (9)0.0446 (3)
H22B−0.032 (3)0.359 (2)0.2128 (15)0.066 (7)*
H22A−0.111 (3)0.470 (2)0.2526 (14)0.069 (7)*
C22−0.0480 (3)−0.07293 (19)0.33556 (13)0.0559 (5)
H22−0.030 (3)−0.160 (2)0.3423 (13)0.061 (6)*
N23−0.2026 (2)0.35240 (16)0.39229 (10)0.0453 (4)
H23B−0.215 (3)0.430 (2)0.3963 (13)0.058 (6)*
H23A−0.232 (3)0.299 (2)0.4342 (14)0.057 (6)*
C23−0.0891 (3)−0.00047 (19)0.26314 (12)0.0526 (5)
H23−0.103 (4)−0.035 (2)0.2163 (15)0.077 (7)*
C24−0.1160 (3)0.12748 (18)0.25641 (10)0.0431 (4)
H24−0.146 (3)0.1764 (18)0.2077 (12)0.048 (5)*
C25−0.1009 (2)0.17539 (15)0.32452 (9)0.0338 (3)
C26−0.1327 (2)0.31196 (15)0.32427 (9)0.0352 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0579 (3)0.0378 (2)0.0333 (2)−0.01169 (18)0.00298 (17)−0.00477 (16)
O10.0845 (12)0.0469 (8)0.0521 (9)0.0040 (8)0.0066 (8)−0.0091 (7)
N10.0551 (9)0.0372 (8)0.0361 (7)−0.0117 (7)−0.0026 (6)−0.0009 (6)
C10.0739 (14)0.0379 (10)0.0502 (11)−0.0197 (9)−0.0090 (10)0.0050 (9)
Cl20.0640 (3)0.0430 (2)0.0393 (2)−0.0127 (2)0.00567 (19)−0.01046 (18)
O20.0740 (10)0.0492 (8)0.0412 (7)−0.0272 (7)0.0026 (7)−0.0098 (6)
N20.0535 (9)0.0310 (7)0.0428 (8)−0.0122 (7)0.0073 (7)−0.0061 (6)
C20.0651 (13)0.0295 (9)0.0749 (14)−0.0119 (8)−0.0056 (11)−0.0094 (9)
Cl30.0642 (3)0.0439 (2)0.0370 (2)−0.0035 (2)0.00486 (19)−0.00088 (18)
O30.0851 (12)0.0472 (8)0.0474 (8)−0.0042 (8)0.0026 (8)−0.0020 (7)
N30.0529 (9)0.0337 (8)0.0407 (8)−0.0116 (7)0.0084 (7)−0.0102 (7)
C30.0654 (13)0.0476 (11)0.0625 (12)−0.0181 (10)0.0094 (10)−0.0280 (10)
C40.0608 (12)0.0435 (10)0.0397 (9)−0.0164 (9)0.0071 (8)−0.0098 (8)
C50.0341 (8)0.0301 (8)0.0375 (8)−0.0047 (6)−0.0016 (6)−0.0056 (6)
C60.0351 (8)0.0304 (8)0.0346 (8)−0.0056 (6)−0.0029 (6)−0.0032 (6)
N110.0463 (8)0.0403 (8)0.0413 (8)−0.0133 (7)−0.0022 (6)−0.0011 (6)
C110.0637 (13)0.0431 (10)0.0535 (11)−0.0168 (9)−0.0050 (10)0.0036 (9)
N120.0662 (11)0.0378 (9)0.0454 (9)−0.0115 (8)−0.0133 (8)0.0036 (7)
C120.0682 (14)0.0369 (10)0.0749 (15)−0.0044 (9)−0.0132 (11)−0.0077 (10)
N130.0533 (9)0.0357 (8)0.0439 (8)−0.0081 (7)−0.0068 (7)−0.0020 (7)
C130.0672 (14)0.0520 (12)0.0582 (12)0.0050 (10)−0.0078 (11)−0.0191 (10)
C140.0487 (10)0.0482 (10)0.0398 (9)−0.0024 (8)−0.0011 (8)−0.0003 (8)
C150.0332 (8)0.0374 (9)0.0389 (8)−0.0072 (7)−0.0064 (7)−0.0013 (7)
C160.0322 (8)0.0416 (9)0.0394 (8)−0.0090 (7)−0.0025 (7)0.0000 (7)
N210.0555 (9)0.0392 (8)0.0350 (7)−0.0006 (7)−0.0085 (6)−0.0053 (6)
C210.0746 (14)0.0421 (10)0.0474 (10)0.0028 (9)−0.0149 (10)−0.0041 (8)
N220.0531 (9)0.0370 (8)0.0395 (8)−0.0089 (7)0.0081 (7)−0.0044 (7)
C220.0681 (14)0.0391 (10)0.0615 (12)−0.0083 (9)−0.0054 (10)−0.0137 (9)
N230.0547 (10)0.0402 (9)0.0387 (8)−0.0099 (7)0.0087 (7)−0.0088 (7)
C230.0634 (13)0.0548 (11)0.0470 (10)−0.0201 (10)−0.0012 (9)−0.0202 (9)
C240.0499 (10)0.0495 (10)0.0328 (8)−0.0184 (8)−0.0036 (7)−0.0046 (7)
C250.0287 (7)0.0381 (8)0.0337 (7)−0.0066 (6)0.0006 (6)−0.0060 (6)
C260.0309 (8)0.0383 (9)0.0355 (8)−0.0074 (7)0.0001 (6)−0.0053 (7)
Geometric parameters (Å, º) top
O1—H1B0.80 (3)N12—H12A0.89 (2)
O1—H100.98 (4)C12—C131.363 (3)
N1—C51.331 (2)C12—H121.00 (3)
N1—C11.334 (2)N13—C161.309 (2)
C1—C21.369 (3)N13—H13B0.92 (2)
C1—H10.92 (2)N13—H13A0.91 (2)
O2—H0B0.85 (3)C13—C141.378 (3)
O2—H0A0.79 (3)C13—H130.87 (3)
N2—C61.311 (2)C14—C151.386 (3)
N2—H2A0.85 (3)C14—H140.91 (2)
N2—H2B0.96 (2)C15—C161.485 (2)
C2—C31.364 (3)N21—C211.333 (2)
C2—H20.96 (2)N21—C251.338 (2)
O3—H03B0.84 (4)C21—C221.381 (3)
O3—H03A0.94 (4)C21—H210.95 (2)
N3—C61.302 (2)N22—C261.307 (2)
N3—H3B0.88 (2)N22—H22B0.89 (3)
N3—H3A0.87 (2)N22—H22A0.91 (2)
C3—C41.384 (3)C22—C231.366 (3)
C3—H30.95 (2)C22—H220.94 (2)
C4—C51.381 (2)N23—C261.311 (2)
C4—H40.94 (2)N23—H23B0.87 (2)
C5—C61.486 (2)N23—H23A0.87 (2)
N11—C151.330 (2)C23—C241.385 (3)
N11—C111.331 (2)C23—H230.97 (2)
C11—C121.390 (3)C24—C251.380 (2)
C11—H110.92 (2)C24—H240.924 (19)
N12—C161.312 (2)C25—C261.492 (2)
N12—H12B0.91 (2)
H1B—O1—H10106 (3)C16—N13—H13A116.6 (13)
C5—N1—C1116.70 (15)H13B—N13—H13A124.4 (19)
N1—C1—C2123.59 (18)C12—C13—C14119.3 (2)
N1—C1—H1117.3 (16)C12—C13—H13117.7 (17)
C2—C1—H1119.1 (16)C14—C13—H13123.0 (17)
H0B—O2—H0A111 (2)C13—C14—C15117.69 (19)
C6—N2—H2A125.2 (16)C13—C14—H14122.7 (13)
C6—N2—H2B124.9 (13)C15—C14—H14119.5 (12)
H2A—N2—H2B110 (2)N11—C15—C14124.30 (16)
C3—C2—C1119.11 (17)N11—C15—C16115.39 (15)
C3—C2—H2122.4 (12)C14—C15—C16120.29 (16)
C1—C2—H2118.5 (12)N13—C16—N12122.82 (17)
H03B—O3—H03A100 (3)N13—C16—C15118.41 (15)
C6—N3—H3B116.3 (14)N12—C16—C15118.77 (16)
C6—N3—H3A122.4 (14)C21—N21—C25116.99 (15)
H3B—N3—H3A120.9 (19)N21—C21—C22122.95 (18)
C2—C3—C4118.91 (18)N21—C21—H21111.6 (13)
C2—C3—H3120.1 (14)C22—C21—H21125.4 (13)
C4—C3—H3121.0 (14)C26—N22—H22B123.0 (15)
C5—C4—C3117.91 (18)C26—N22—H22A124.0 (15)
C5—C4—H4121.0 (13)H22B—N22—H22A113 (2)
C3—C4—H4121.1 (13)C23—C22—C21119.16 (18)
N1—C5—C4123.74 (15)C23—C22—H22121.3 (13)
N1—C5—C6114.14 (13)C21—C22—H22119.5 (13)
C4—C5—C6122.09 (15)C26—N23—H23B121.2 (15)
N3—C6—N2122.05 (15)C26—N23—H23A118.2 (14)
N3—C6—C5118.14 (15)H23B—N23—H23A121 (2)
N2—C6—C5119.81 (15)C22—C23—C24119.30 (17)
C15—N11—C11116.63 (16)C22—C23—H23122.4 (15)
N11—C11—C12123.22 (19)C24—C23—H23118.3 (15)
N11—C11—H11119.1 (14)C25—C24—C23117.51 (17)
C12—C11—H11117.7 (14)C25—C24—H24123.3 (12)
C16—N12—H12B124.8 (13)C23—C24—H24119.2 (12)
C16—N12—H12A121.0 (15)N21—C25—C24124.10 (15)
H12B—N12—H12A114.1 (19)N21—C25—C26114.20 (14)
C13—C12—C11118.88 (19)C24—C25—C26121.68 (15)
C13—C12—H12124.1 (15)N22—C26—N23122.63 (16)
C11—C12—H12117.0 (15)N22—C26—C25119.59 (15)
C16—N13—H13B119.0 (13)N23—C26—C25117.78 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N23—H23B···O1i0.87 (2)1.97 (2)2.829 (2)173 (2)
N22—H22B···Cl10.89 (3)2.31 (3)3.187 (2)169 (2)
N12—H12B···Cl3ii0.91 (2)2.35 (2)3.2522 (19)170.2 (18)
O1—H1B···Cl30.80 (3)2.37 (3)3.163 (2)169 (2)
N2—H2A···Cl2iii0.85 (3)2.49 (3)3.326 (2)167 (2)
O1—H10···Cl2iv0.98 (4)2.22 (4)3.1902 (19)173 (3)
N3—H3A···O20.87 (2)1.94 (2)2.808 (2)174.9 (19)
N2—H2B···Cl10.96 (2)2.32 (2)3.2754 (17)170.9 (17)
N12—H12A···Cl3v0.89 (2)2.43 (2)3.313 (2)171 (2)
N23—H23A···Cl3vi0.87 (2)2.50 (2)3.324 (2)158 (2)
N13—H13B···O3ii0.92 (2)1.97 (2)2.883 (2)178 (2)
N22—H22A···Cl2iii0.91 (2)2.43 (3)3.3194 (18)168 (2)
N13—H13A···Cl10.91 (2)2.48 (2)3.335 (2)156.9 (19)
O3—H03B···Cl2iv0.84 (4)2.45 (4)3.286 (2)174 (3)
O2—H0B···Cl10.85 (3)2.28 (3)3.1171 (18)172 (2)
O2—H0A···Cl20.79 (3)2.40 (3)3.1833 (18)175 (3)
O3—H03A···Cl30.94 (4)2.25 (4)3.1586 (18)164 (3)
Symmetry codes: (i) x−1, y, z; (ii) x, y−1, z; (iii) −x, −y+1, −z; (iv) −x+1, −y+1, −z; (v) −x+1, −y+1, −z+1; (vi) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formulaC6H8N3+·Cl−·H2O
Mr175.62
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)7.2570 (15), 11.146 (2), 16.862 (3)
α, β, γ (°)79.24 (3), 82.14 (3), 78.34 (3)
V (Å3)1305.3 (5)
Z6
Radiation typeMo Kα
µ (mm−1)0.39
Crystal size (mm)0.25 × 0.24 × 0.22
Data collection
DiffractometerRigaku R-AXIS RAPID
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.909, 0.918
No. of measured, independent and
observed [I > 2σ(I)] reflections		12872, 5919, 4550
Rint0.024
(sin θ/λ)max (Å−1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.117, 1.11
No. of reflections5919
No. of parameters418
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å−3)0.23, −0.26

Computer programs: RAPID-AUTO (Rigaku, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999) and SHELXP97 (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N23—H23B···O1i0.87 (2)1.97 (2)2.829 (2)173 (2)
N22—H22B···Cl10.89 (3)2.31 (3)3.187 (2)169 (2)
N12—H12B···Cl3ii0.91 (2)2.35 (2)3.2522 (19)170.2 (18)
O1—H1B···Cl30.80 (3)2.37 (3)3.163 (2)169 (2)
N2—H2A···Cl2iii0.85 (3)2.49 (3)3.326 (2)167 (2)
O1—H10···Cl2iv0.98 (4)2.22 (4)3.1902 (19)173 (3)
N3—H3A···O20.87 (2)1.94 (2)2.808 (2)174.9 (19)
N2—H2B···Cl10.96 (2)2.32 (2)3.2754 (17)170.9 (17)
N12—H12A···Cl3v0.89 (2)2.43 (2)3.313 (2)171 (2)
N23—H23A···Cl3vi0.87 (2)2.50 (2)3.324 (2)158 (2)
N13—H13B···O3ii0.92 (2)1.97 (2)2.883 (2)178 (2)
N22—H22A···Cl2iii0.91 (2)2.43 (3)3.3194 (18)168 (2)
N13—H13A···Cl10.91 (2)2.48 (2)3.335 (2)156.9 (19)
O3—H03B···Cl2iv0.84 (4)2.45 (4)3.286 (2)174 (3)
O2—H0B···Cl10.85 (3)2.28 (3)3.1171 (18)172 (2)
O2—H0A···Cl20.79 (3)2.40 (3)3.1833 (18)175 (3)
O3—H03A···Cl30.94 (4)2.25 (4)3.1586 (18)164 (3)
Symmetry codes: (i) x−1, y, z; (ii) x, y−1, z; (iii) −x, −y+1, −z; (iv) −x+1, −y+1, −z; (v) −x+1, −y+1, −z+1; (vi) −x, −y+1, −z+1.
 

Acknowledgements

The authors gratefully acknowledge financial support from the Education Department of Liaoning Province (2009 A 265) and Liaoning University.

References

First citationBrandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
 First citationFan, P., Wang, L. & Zhang, H. (2009). Acta Cryst. E65, o2408.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationGóker, H., Ózden, S., Yildiz, S. & Boykin, D. W. (2005). Eur. J. Med. Chem. 40, 1062–1069.  Web of Science PubMed Google Scholar
 First citationGuo, J., Wong, W.-K. & Wong, W.-Y. (2005). Polyhedron, 24, 927–939.  Web of Science CSD CrossRef CAS Google Scholar
 First citationHigashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.  Google Scholar
 First citationRigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWalther, M., Wermann, H., Lutsche, M., Gúnther, W., Górls, H. & Anders, E. (2006). J. Org. Chem. 71, 1399–1406.  Web of Science CSD CrossRef PubMed CAS Google Scholar

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ISSN: 2056-9890
Volume 66| Part 12| December 2010| Page o3169
https://doi.org/10.1107/S1600536810046106
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