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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 68| Part 6| June 2012| Page o1895
doi:10.1107/S1600536812022866

4-[(Adamantan-1-yl)carbamo­yl]pyridinium chloride

Ying-Chun Wanga*

aCollege of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
*Correspondence e-mail: wangyc33@yahoo.com.cn

(Received 16 May 2012; accepted 19 May 2012; online 26 May 2012)

In the title salt, C16H21N2O+·Cl−, the amide group makes a dihedral angle of 24.98 (2)° with respect to the pyridinium ring. In the crystal, both the amide and pyridinium N atoms are involved in N—H⋯Cl hydrogen bonding. Weak inter­molecular C—H⋯Cl and C—H⋯O inter­actions also occur.

Related literature

For the structures and properties of related compounds, see: Fu et al. (2011a[Fu, D.-W., Zhang, W., Cai, H.-L., Zhang, Y., Ge, J.-Z., Xiong, R.-G. & Huang, S. P. D. (2011a). J. Am. Chem. Soc. 133, 12780-12786.],b[Fu, D.-W., Zhang, W., Cai, H.-L., Zhang, Y., Ge, J.-Z., Xiong, R.-G., Huang, S. P. D. & Nakamura, T. (2011b). Angew. Chem. Int. Ed. 50, 11947-11951.],c[Fu, D.-W., Zhang, W., Cai, H.-L., Ge, J.-Z., Zhang, Y. & Xiong, R.-G. (2011c). Adv. Mater. 23, 5658-5662.]); Dai & Chen (2011[Dai, J. & Chen, X.-Y. (2011). Acta Cryst. E67, o287.]); Xu et al. (2011[Xu, R.-J., Fu, D.-W., Dai, J., Zhang, Y., Ge, J.-Z. & Ye, H.-Y. (2011). Inorg. Chem. Commun. 14, 1093-1096.]); Zheng (2011[Zheng, W.-N. (2011). Acta Cryst. E67, m344.]).

[Scheme 1]

Experimental

Crystal data

  • C16H21N2O+·Cl−

  • Mr = 292.80

  • Monoclinic, P 21 /n

  • a = 7.072 (4) Å

  • b = 22.691 (13) Å

  • c = 8.905 (6) Å

  • β = 91.703 (7)°

  • V = 1428.3 (15) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.27 mm−1

  • T = 93 K

  • 0.10 × 0.03 × 0.03 mm
Data collection

  • Rigaku Mercury2 diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.910, Tmax = 1.000

  • 13912 measured reflections

  • 3278 independent reflections

  • 2863 reflections with I > 2σ(I)

  • Rint = 0.041
Refinement

  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.157

  • S = 1.19

  • 3278 reflections

  • 181 parameters

  • H-atom parameters constrained

  • Δρmax = 0.54 e Å−3

  • Δρmin = −0.43 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1A⋯Cl1i 0.86 2.19 3.020 (2) 161
N2—H2A⋯Cl1 0.86 2.51 3.272 (2) 148
C1—H1B⋯Cl1ii 0.95 2.77 3.520 (3) 136
C2—H2B⋯Cl1iii 0.95 2.76 3.494 (3) 134
C5—H5A⋯O1iv 0.95 2.31 3.149 (3) 147
Symmetry codes: (i) -x+2, -y, -z+2; (ii) x, y, z+1; (iii) -x+1, -y, -z+2; (iv) x+1, y, z.

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812022866/xu5543sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812022866/xu5543Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812022866/xu5543Isup3.cml

checkCIF report


Comment top

Organic amino compounds attracted more attention as phase transition dielectric materials for its application in memory storage (Fu et al., 2011a, b and c). With the purpose of obtaining phase transition crystals of amino compounds, various amines have been studied and we have elaborated a series of new materials with this organic molecules (Dai & Chen 2011; Xu, et al. 2011; Zheng 2011). In this study, we describe the crystal structure of the title compound, 4-[(adamantyl)carbamoyl]pyridinium chloride.

The asymmetric unit is composed of one 4-[(adamantyl)carbamoyl]pyridinium cation and one chloride anion. The pyridine N atom was protonated, and the amide group makes a dihedral angle of 24.98 (2)° with respect to the pyridinium ring (Fig.1). The torsion angles of C2—C3—C6—O1 and C2—C3—C6—N2 are 23.6 (3)° and -158.1 (4)°, C4—C3—C6—O1 and C4—C3—C6—N2 are -152.3 (2)° and 26.0 (3)°. Intermolecular N—H···Cl bonds and weak C—H···Cl and C—H···O contacts link ions into a network parallel to (0 1 0) plane (Table 1 and Fig 2).

Related literature top

For the structures and properties of related compounds, see: Fu et al. (2011a,b,c); Dai & Chen (2011); Xu et al. (2011); Zheng (2011).

Experimental top

Isonicotinic acid 5 g was added in thionyl chloride (50 ml), and the mixture reacted at 353 K for 5 h. Then the solvate was removed under reduced pressure, the isonicotinoyl chloride was obtained. The 1-aminodiamantane hydrochloride (10 mmol) and triethylamine 2.02 g (20 mmol) dissolved in chloroform (40 ml) at 273 K, then the isonicotinoyl chloride 1.51 g (10 mmol) was added. Then the reactant mixture was stired for 7 h at room temperature and some flaxen solid appeared. After filtering the mixture, the solid was dissolved in water and was neutralized with sodium carbonate, The mixed solution was extracted by dichloromethane. The N-(1-adamantyl)isonicotinamide was obtained when the dichloromethane was evaporated under reduced pressure. A mixture of N(1-adamantyl)isonicotinamide 2.56 g (10 mmol), HCl (2.0 mL, 6 mol/L), and 20 mL ethanol were added into a 50ml flask and refluxed for 5 hours, then cooled and filtrated. The solution was evaporated slowly in the air. Colorless block crystals suitable for X-ray analysis were obtained after one week.

Refinement top

All H atoms attached to C atoms were fixed geometrically and treated as riding with C-H = 0.95 Å (aromatic), C-H = 0.99 Å (methylene) and C-H = 1.00 Å (methine) with Uiso(H) = 1.2Ueq(C). H atoms bonded to N atoms were located in difference Fourier maps and restrained with the H—N = 0.86 (2)Å. In the last stage of refinement they were treated as riding on the N atoms with Uiso(H) = 1.2Ueq(N).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular view of the title compound with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. The crystal packing of the title compound viewed along the c axis showing the hydrogen bondings unit (dashed line).
4-[(Adamantan-1-yl)carbamoyl]pyridinium chloride top
Crystal data top
C16H21N2O+·Cl−F(000) = 624
Mr = 292.80Dx = 1.362 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3278 reflections
a = 7.072 (4) Åθ = 1.8–27.5°
b = 22.691 (13) ŵ = 0.27 mm−1
c = 8.905 (6) ÅT = 93 K
β = 91.703 (7)°Block, colourless
V = 1428.3 (15) Å30.10 × 0.03 × 0.03 mm
Z = 4
Data collection top
Rigaku Mercury2
diffractometer		3278 independent reflections
Radiation source: fine-focus sealed tube2863 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
Detector resolution: 13.6612 pixels mm-1θmax = 27.5°, θmin = 1.8°
CCD profile fitting scansh = −9→9
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		k = −29→29
Tmin = 0.910, Tmax = 1.000l = −11→11
13912 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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157H-atom parameters constrained
S = 1.19 w = 1/[σ2(Fo2) + (0.0868P)2 + 0.3419P]
where P = (Fo2 + 2Fc2)/3
3278 reflections(Δ/σ)max < 0.001
181 parametersΔρmax = 0.54 e Å−3
0 restraintsΔρmin = −0.43 e Å−3
Crystal data top
C16H21N2O+·Cl−V = 1428.3 (15) Å3
Mr = 292.80Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.072 (4) ŵ = 0.27 mm−1
b = 22.691 (13) ÅT = 93 K
c = 8.905 (6) Å0.10 × 0.03 × 0.03 mm
β = 91.703 (7)°
Data collection top
Rigaku Mercury2
diffractometer		3278 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		2863 reflections with I > 2σ(I)
Tmin = 0.910, Tmax = 1.000Rint = 0.041
13912 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.157H-atom parameters constrained
S = 1.19Δρmax = 0.54 e Å−3
3278 reflectionsΔρmin = −0.43 e Å−3
181 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
N20.4961 (2)0.11853 (7)0.77561 (19)0.0136 (4)
H2A0.60140.10440.74570.016*
O10.3053 (2)0.12500 (7)0.97887 (17)0.0195 (4)
N10.8767 (2)0.03797 (7)1.21603 (19)0.0150 (4)
H1A0.96040.02301.27680.018*
C40.8026 (3)0.08813 (9)0.9896 (2)0.0157 (4)
H4A0.84250.10690.90060.019*
C80.4853 (3)0.15358 (9)0.5188 (2)0.0154 (4)
H8A0.51540.11350.48300.018*
H8B0.60580.17480.53890.018*
C120.3246 (3)0.24905 (9)0.4539 (2)0.0169 (4)
H12A0.44460.27060.47350.020*
H12B0.25000.27090.37620.020*
C60.4548 (3)0.11078 (9)0.9207 (2)0.0143 (4)
C70.3740 (3)0.14958 (8)0.6638 (2)0.0123 (4)
C30.6104 (3)0.08371 (8)1.0195 (2)0.0127 (4)
C20.5567 (3)0.05623 (9)1.1516 (2)0.0153 (4)
H2B0.42670.05311.17430.018*
C90.3315 (3)0.21225 (8)0.7186 (2)0.0146 (4)
H9A0.26110.21030.81290.018*
H9B0.45150.23360.73950.018*
C130.2134 (3)0.24535 (8)0.5982 (2)0.0151 (4)
H13A0.18590.28610.63460.018*
C50.9336 (3)0.06493 (9)1.0909 (2)0.0169 (4)
H5A1.06480.06801.07220.020*
C100.1881 (3)0.11626 (8)0.6305 (2)0.0143 (4)
H10A0.11600.11260.72370.017*
H10B0.21600.07610.59380.017*
C160.1811 (3)0.15352 (9)0.3664 (2)0.0161 (4)
H16A0.20810.11330.32960.019*
H16B0.10520.17440.28770.019*
C150.0694 (3)0.14989 (9)0.5109 (2)0.0146 (4)
H15A−0.05200.12840.49020.017*
C10.6932 (3)0.03367 (9)1.2493 (2)0.0165 (4)
H1B0.65760.01511.33980.020*
C140.0263 (3)0.21217 (9)0.5695 (2)0.0157 (4)
H14A−0.05340.23370.49460.019*
H14B−0.04380.20950.66390.019*
C110.3670 (3)0.18655 (9)0.3972 (2)0.0163 (4)
H11A0.43960.18900.30280.020*
Cl10.77720 (7)0.01868 (2)0.63897 (5)0.01459 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N20.0114 (8)0.0184 (8)0.0110 (8)0.0036 (6)0.0002 (7)0.0022 (6)
O10.0137 (8)0.0295 (8)0.0154 (8)0.0054 (6)0.0025 (6)0.0056 (6)
N10.0154 (9)0.0175 (8)0.0120 (8)0.0031 (6)−0.0045 (7)0.0002 (6)
C40.0164 (11)0.0172 (10)0.0135 (10)−0.0002 (7)0.0005 (8)0.0011 (7)
C80.0145 (10)0.0183 (10)0.0134 (10)0.0036 (7)0.0008 (8)0.0020 (7)
C120.0178 (11)0.0159 (10)0.0167 (10)0.0001 (7)−0.0017 (8)0.0032 (7)
C60.0126 (10)0.0156 (10)0.0146 (10)0.0001 (7)−0.0017 (8)0.0015 (7)
C70.0109 (9)0.0141 (9)0.0117 (9)0.0010 (7)−0.0020 (7)0.0007 (7)
C30.0134 (10)0.0133 (9)0.0114 (9)0.0009 (7)−0.0013 (8)−0.0009 (7)
C20.0137 (10)0.0173 (9)0.0149 (10)0.0018 (7)0.0004 (8)0.0019 (8)
C90.0161 (10)0.0145 (10)0.0130 (10)0.0011 (7)−0.0015 (8)−0.0002 (7)
C130.0175 (10)0.0119 (9)0.0158 (10)0.0018 (7)0.0000 (8)0.0001 (7)
C50.0136 (10)0.0183 (10)0.0186 (11)−0.0007 (7)−0.0024 (8)−0.0018 (7)
C100.0150 (10)0.0138 (9)0.0141 (10)−0.0011 (7)−0.0015 (8)0.0030 (7)
C160.0179 (10)0.0177 (10)0.0124 (10)0.0029 (8)−0.0036 (8)0.0008 (7)
C150.0129 (10)0.0163 (10)0.0142 (10)−0.0014 (7)−0.0034 (8)0.0000 (7)
C10.0196 (11)0.0163 (10)0.0138 (10)0.0020 (8)0.0014 (8)0.0003 (8)
C140.0140 (10)0.0183 (10)0.0148 (10)0.0040 (7)0.0004 (8)0.0038 (7)
C110.0163 (10)0.0193 (10)0.0133 (10)0.0023 (8)0.0014 (8)0.0027 (7)
Cl10.0136 (3)0.0161 (3)0.0139 (3)0.00244 (16)−0.00125 (19)0.00123 (16)
Geometric parameters (Å, º) top
N2—C61.345 (3)C2—C11.378 (3)
N2—C71.478 (2)C2—H2B0.9500
N2—H2A0.8600C9—C131.536 (3)
O1—C61.234 (3)C9—H9A0.9900
N1—C11.343 (3)C9—H9B0.9900
N1—C51.343 (3)C13—C141.537 (3)
N1—H1A0.8600C13—H13A1.0000
C4—C51.378 (3)C5—H5A0.9500
C4—C31.396 (3)C10—C151.539 (3)
C4—H4A0.9500C10—H10A0.9900
C8—C71.534 (3)C10—H10B0.9900
C8—C111.542 (3)C16—C111.531 (3)
C8—H8A0.9900C16—C151.532 (3)
C8—H8B0.9900C16—H16A0.9900
C12—C131.529 (3)C16—H16B0.9900
C12—C111.538 (3)C15—C141.540 (3)
C12—H12A0.9900C15—H15A1.0000
C12—H12B0.9900C1—H1B0.9500
C6—C31.518 (3)C14—H14A0.9900
C7—C91.536 (3)C14—H14B0.9900
C7—C101.538 (3)C11—H11A1.0000
C3—C21.394 (3)
C6—N2—C7124.78 (17)C12—C13—C9109.36 (17)
C6—N2—H2A117.6C12—C13—C14110.43 (17)
C7—N2—H2A117.6C9—C13—C14108.90 (16)
C1—N1—C5122.08 (18)C12—C13—H13A109.4
C1—N1—H1A118.9C9—C13—H13A109.4
C5—N1—H1A119.0C14—C13—H13A109.4
C5—C4—C3119.15 (19)N1—C5—C4120.3 (2)
C5—C4—H4A120.4N1—C5—H5A119.8
C3—C4—H4A120.4C4—C5—H5A119.8
C7—C8—C11109.77 (17)C7—C10—C15109.57 (16)
C7—C8—H8A109.7C7—C10—H10A109.8
C11—C8—H8A109.7C15—C10—H10A109.8
C7—C8—H8B109.7C7—C10—H10B109.8
C11—C8—H8B109.7C15—C10—H10B109.8
H8A—C8—H8B108.2H10A—C10—H10B108.2
C13—C12—C11109.58 (16)C11—C16—C15109.68 (16)
C13—C12—H12A109.8C11—C16—H16A109.7
C11—C12—H12A109.8C15—C16—H16A109.7
C13—C12—H12B109.8C11—C16—H16B109.7
C11—C12—H12B109.8C15—C16—H16B109.7
H12A—C12—H12B108.2H16A—C16—H16B108.2
O1—C6—N2125.65 (19)C16—C15—C10108.92 (17)
O1—C6—C3118.52 (18)C16—C15—C14110.33 (16)
N2—C6—C3115.80 (18)C10—C15—C14109.25 (16)
N2—C7—C8106.92 (16)C16—C15—H15A109.4
N2—C7—C9110.06 (16)C10—C15—H15A109.4
C8—C7—C9108.83 (16)C14—C15—H15A109.4
N2—C7—C10112.01 (16)N1—C1—C2119.81 (19)
C8—C7—C10108.93 (17)N1—C1—H1B120.1
C9—C7—C10110.00 (16)C2—C1—H1B120.1
C2—C3—C4118.94 (18)C13—C14—C15109.11 (16)
C2—C3—C6117.35 (18)C13—C14—H14A109.9
C4—C3—C6123.59 (18)C15—C14—H14A109.9
C1—C2—C3119.7 (2)C13—C14—H14B109.9
C1—C2—H2B120.2C15—C14—H14B109.9
C3—C2—H2B120.2H14A—C14—H14B108.3
C13—C9—C7109.76 (16)C16—C11—C12109.60 (17)
C13—C9—H9A109.7C16—C11—C8109.48 (17)
C7—C9—H9A109.7C12—C11—C8108.91 (17)
C13—C9—H9B109.7C16—C11—H11A109.6
C7—C9—H9B109.7C12—C11—H11A109.6
H9A—C9—H9B108.2C8—C11—H11A109.6
C7—N2—C6—O14.8 (3)C7—C9—C13—C1460.4 (2)
C7—N2—C6—C3−173.33 (16)C1—N1—C5—C4−1.6 (3)
C6—N2—C7—C8174.15 (18)C3—C4—C5—N10.6 (3)
C6—N2—C7—C956.1 (2)N2—C7—C10—C15−178.66 (16)
C6—N2—C7—C10−66.6 (2)C8—C7—C10—C15−60.6 (2)
C11—C8—C7—N2−179.08 (15)C9—C7—C10—C1558.6 (2)
C11—C8—C7—C9−60.2 (2)C11—C16—C15—C10−60.5 (2)
C11—C8—C7—C1059.7 (2)C11—C16—C15—C1459.4 (2)
C5—C4—C3—C20.4 (3)C7—C10—C15—C1661.0 (2)
C5—C4—C3—C6176.27 (18)C7—C10—C15—C14−59.6 (2)
O1—C6—C3—C223.6 (3)C5—N1—C1—C21.5 (3)
N2—C6—C3—C2−158.06 (18)C3—C2—C1—N1−0.4 (3)
O1—C6—C3—C4−152.3 (2)C12—C13—C14—C1558.6 (2)
N2—C6—C3—C426.0 (3)C9—C13—C14—C15−61.5 (2)
C4—C3—C2—C1−0.5 (3)C16—C15—C14—C13−58.5 (2)
C6—C3—C2—C1−176.61 (18)C10—C15—C14—C1361.2 (2)
N2—C7—C9—C13176.98 (16)C15—C16—C11—C12−59.6 (2)
C8—C7—C9—C1360.1 (2)C15—C16—C11—C859.8 (2)
C10—C7—C9—C13−59.1 (2)C13—C12—C11—C1659.6 (2)
C11—C12—C13—C960.3 (2)C13—C12—C11—C8−60.1 (2)
C11—C12—C13—C14−59.5 (2)C7—C8—C11—C16−59.5 (2)
C7—C9—C13—C12−60.4 (2)C7—C8—C11—C1260.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···Cl1i0.862.193.020 (2)161
N2—H2A···Cl10.862.513.272 (2)148
C1—H1B···Cl1ii0.952.773.520 (3)136
C2—H2B···Cl1iii0.952.763.494 (3)134
C5—H5A···O1iv0.952.313.149 (3)147
Symmetry codes: (i) −x+2, −y, −z+2; (ii) x, y, z+1; (iii) −x+1, −y, −z+2; (iv) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC16H21N2O+·Cl−
Mr292.80
Crystal system, space groupMonoclinic, P21/n
Temperature (K)93
a, b, c (Å)7.072 (4), 22.691 (13), 8.905 (6)
β (°) 91.703 (7)
V (Å3)1428.3 (15)
Z4
Radiation typeMo Kα
µ (mm−1)0.27
Crystal size (mm)0.10 × 0.03 × 0.03
Data collection
DiffractometerRigaku Mercury2
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2005)
Tmin, Tmax0.910, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections		13912, 3278, 2863
Rint0.041
(sin θ/λ)max (Å−1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.157, 1.19
No. of reflections3278
No. of parameters181
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.54, −0.43

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···Cl1i0.862.193.020 (2)160.8
N2—H2A···Cl10.862.513.272 (2)148.1
C1—H1B···Cl1ii0.952.773.520 (3)136
C2—H2B···Cl1iii0.952.763.494 (3)134
C5—H5A···O1iv0.952.313.149 (3)147
Symmetry codes: (i) −x+2, −y, −z+2; (ii) x, y, z+1; (iii) −x+1, −y, −z+2; (iv) x+1, y, z.
 

Acknowledgements

This work was supported by the Doctoral Foundation of Southeast University, China.

References

First citationDai, J. & Chen, X.-Y. (2011). Acta Cryst. E67, o287.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationFu, D.-W., Zhang, W., Cai, H.-L., Ge, J.-Z., Zhang, Y. & Xiong, R.-G. (2011c). Adv. Mater. 23, 5658–5662.  Web of Science CSD CrossRef CAS PubMed Google Scholar
 First citationFu, D.-W., Zhang, W., Cai, H.-L., Zhang, Y., Ge, J.-Z., Xiong, R.-G. & Huang, S. P. D. (2011a). J. Am. Chem. Soc. 133, 12780–12786.  Web of Science CSD CrossRef CAS PubMed Google Scholar
 First citationFu, D.-W., Zhang, W., Cai, H.-L., Zhang, Y., Ge, J.-Z., Xiong, R.-G., Huang, S. P. D. & Nakamura, T. (2011b). Angew. Chem. Int. Ed. 50, 11947–11951.  Web of Science CSD CrossRef CAS Google Scholar
 First citationRigaku (2005). CrystalClear. 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 citationXu, R.-J., Fu, D.-W., Dai, J., Zhang, Y., Ge, J.-Z. & Ye, H.-Y. (2011). Inorg. Chem. Commun. 14, 1093–1096.  Web of Science CSD CrossRef CAS Google Scholar
 First citationZheng, W.-N. (2011). Acta Cryst. E67, m344.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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ISSN: 2056-9890
Volume 68| Part 6| June 2012| Page o1895
doi:10.1107/S1600536812022866
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