4,4′-(Propane-1,3-di­yl)dipiperidinium sulfate monohydrate

Yang, E.; Song, X.-C.; Zhuang, R.-Q.

doi:10.1107/S1600536808025300

organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1763

doi:10.1107/S1600536808025300

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4,4′-(Propane-1,3-diyl)dipiperidinium sulfate monohydrate

E Yang,^a ^* Xu-Chun Song ^a and Rong-Qiang Zhuang ^b

^aCollege of Chemistry and Materials Science, Fujian Normal University, Fuzhou 350007, People's Republic of China, and ^bCollege of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, People's Republic of China
^*Correspondence e-mail: yangeli66@yahoo.com.cn

(Received 19 July 2008; accepted 6 August 2008; online 16 August 2008)

In the title compound, C₁₃H₂₈N₂²⁺·SO₄²⁻·H₂O, extensive hydrogen-bonding interactions between the protonated 4,4′-(propane-1,3-diyl)dipiperidinium ions, the sulfate anions and the water molecules lead to a three-dimensional pillared and layered structure with the 4,4′-(propane-1,3-diyl)dipiperidinium ions acting as the pillars.

Experimental

Crystal data

C₁₃H₂₈N₂²⁺·SO₄²⁻·H₂O
M_r = 326.45
Monoclinic, P 2₁ /n
a = 6.2019 (2) Å
b = 22.5110 (5) Å
c = 12.0052 (3) Å
β = 100.439 (2)°
V = 1648.32 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 293 (2) K
0.22 × 0.14 × 0.09 mm

Data collection

Siemens SMART 1K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.927, T_max = 0.98
13022 measured reflections
2932 independent reflections
2011 reflections with I > 2σ(I)
R_int = 0.066

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.131
S = 1.03
2932 reflections
202 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O4ⁱ	0.85	1.98	2.819 (3)	168
O1W—H1WB⋯O3ⁱⁱ	0.85	1.97	2.799 (3)	165
N1—H1NA⋯O4ⁱⁱⁱ	0.94 (3)	2.09 (3)	2.904 (3)	144 (3)
N1—H1NB⋯O3^iv	0.85 (3)	1.91 (3)	2.711 (3)	157 (3)
N2—H2NA⋯O1^v	0.88 (3)	1.83 (3)	2.704 (3)	177 (3)
N2—H2NB⋯O4^vi	0.92 (3)	2.02 (3)	2.845 (4)	149 (3)
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) -x, -y, -z+1; (iv) -x+1, -y, -z+1; (v) x+1, y, z; (vi) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Bergerhoff et al., 1999 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808025300/fj2138sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808025300/fj2138Isup2.hkl

checkCIF report

Comment top

The asymmetric unit of the title compound, (I), consists of one protonated 4,4'-(propane-1,3-diyl)dipiperidinium ion, one deprotonated sulfate anion and one water molecule (Figure 1). Both protonated N ends of the 4,4'-(propane-1,3-diyl)dipiperidinium ion form N—H···O hydrogen bonds with the sulfate anion, as well as the water molecules form O—H···O hydrogen bonds with the sulfate anion, which leads to the formation of two-dimensional hydrogen-bonding layer parallel to the ac plane (Table 1 & Figure 2). The resulting layers are further pillared by the 4,4'-(propane-1,3-diyl)dipiperidinium ions to complete the three-dimensional structure.

Related literature top

Please supply any relevant related literature.

Experimental top

A solution of 4,4-trimethylenedipiperidine (1 mmol), sulfuric acid (1 mmol) and H₂O (10 ml) was slowly evaporated at room temperature, giving colorless single crystals suitable for X-ray analysis.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Bergerhoff et al., 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the title compound, showing 30% probability displacement ellipsoids.
	Fig. 2. The three-dimensional structure of the title compound, showing the hydrogen bonding interactions (dashed lines).

4,4'-(Propane-1,3-diyl)dipiperidinium sulfate monohydrate top

Crystal data top

C₁₃H₂₈N₂²⁺·SO₄²⁻·H₂O	F(000) = 712
M_r = 326.45	D_x = 1.315 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 99 reflections
a = 6.2019 (2) Å	θ = 2.0–25.1°
b = 22.5110 (5) Å	µ = 0.22 mm⁻¹
c = 12.0052 (3) Å	T = 293 K
β = 100.439 (2)°	Prism, colorless
V = 1648.32 (8) Å³	0.22 × 0.14 × 0.09 mm
Z = 4

Data collection top

Siemens SMART 1K CCD area-detector diffractometer	2932 independent reflections
Radiation source: fine-focus sealed tube	2011 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.066
ϕ and ω scans	θ_max = 25.1°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
T_min = 0.927, T_max = 0.98	k = −26→26
13022 measured reflections	l = −13→14

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0635P)² + 0.5599P] where P = (F_o² + 2F_c²)/3
2932 reflections	(Δ/σ)_max < 0.001
202 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₁₃H₂₈N₂²⁺·SO₄²⁻·H₂O	V = 1648.32 (8) Å³
M_r = 326.45	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.2019 (2) Å	µ = 0.22 mm⁻¹
b = 22.5110 (5) Å	T = 293 K
c = 12.0052 (3) Å	0.22 × 0.14 × 0.09 mm
β = 100.439 (2)°

Data collection top

Siemens SMART 1K CCD area-detector diffractometer	2932 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2011 reflections with I > 2σ(I)
T_min = 0.927, T_max = 0.98	R_int = 0.066
13022 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.34 e Å⁻³
2932 reflections	Δρ_min = −0.40 e Å⁻³
202 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

	x	y	z	U_iso*/U_eq
S1	0.28582 (11)	0.18642 (3)	0.35885 (6)	0.0255 (2)
O1W	0.7186 (3)	−0.20465 (10)	0.15532 (19)	0.0458 (6)
H1WA	0.6074	−0.2274	0.1421	0.069*
H1WB	0.8181	−0.2279	0.1410	0.069*
O1	0.2335 (3)	0.19986 (9)	0.23718 (16)	0.0346 (5)
O2	0.2510 (4)	0.12374 (10)	0.38116 (19)	0.0489 (6)
O3	0.5164 (3)	0.20349 (10)	0.40084 (18)	0.0431 (6)
O4	0.1467 (3)	0.22203 (10)	0.42124 (19)	0.0493 (7)
N1	0.1395 (4)	−0.13893 (12)	0.4911 (2)	0.0310 (6)
H1NA	0.026 (5)	−0.1498 (14)	0.529 (3)	0.046*
H1NB	0.258 (6)	−0.1500 (14)	0.533 (3)	0.046*
N2	0.8705 (4)	0.19250 (11)	0.0746 (2)	0.0279 (6)
H2NA	0.986 (5)	0.1962 (14)	0.128 (3)	0.042*
H2NB	0.851 (5)	0.2258 (14)	0.029 (3)	0.042*
C1	0.1335 (5)	−0.07379 (13)	0.4752 (3)	0.0328 (7)
H1A	0.1482	−0.0545	0.5484	0.039*
H1B	−0.0068	−0.0624	0.4306	0.039*
C2	0.3159 (5)	−0.05304 (13)	0.4160 (2)	0.0279 (7)
H2A	0.4555	−0.0589	0.4661	0.033*
H2B	0.2987	−0.0108	0.4007	0.033*
C3	0.3192 (4)	−0.08591 (12)	0.3044 (2)	0.0249 (6)
H3A	0.1859	−0.0756	0.2507	0.030*
C4	0.3183 (5)	−0.15306 (12)	0.3261 (2)	0.0300 (7)
H4A	0.3080	−0.1739	0.2546	0.036*
H4B	0.4554	−0.1643	0.3739	0.036*
C5	0.1292 (5)	−0.17174 (14)	0.3825 (2)	0.0351 (8)
H5A	−0.0087	−0.1634	0.3326	0.042*
H5B	0.1369	−0.2141	0.3972	0.042*
C6	0.5170 (5)	−0.06873 (12)	0.2525 (2)	0.0297 (7)
H6A	0.5259	−0.0957	0.1905	0.036*
H6B	0.6483	−0.0743	0.3092	0.036*
C7	0.5158 (4)	−0.00503 (12)	0.2080 (3)	0.0296 (7)
H7A	0.3918	−0.0001	0.1466	0.036*
H7B	0.4964	0.0222	0.2681	0.036*
C8	0.7255 (5)	0.01124 (13)	0.1655 (3)	0.0315 (7)
H8A	0.8465	0.0112	0.2293	0.038*
H8B	0.7549	−0.0191	0.1129	0.038*
C9	0.6696 (5)	0.18163 (13)	0.1245 (3)	0.0298 (7)
H9A	0.5413	0.1820	0.0647	0.036*
H9B	0.6536	0.2132	0.1774	0.036*
C10	0.6836 (4)	0.12266 (12)	0.1851 (2)	0.0269 (7)
H10A	0.5494	0.1160	0.2141	0.032*
H10B	0.8042	0.1236	0.2491	0.032*
C11	0.7181 (4)	0.07147 (12)	0.1069 (2)	0.0264 (7)
H11A	0.5943	0.0712	0.0433	0.032*
C12	0.9259 (5)	0.08438 (13)	0.0598 (3)	0.0332 (7)
H12A	1.0508	0.0844	0.1215	0.040*
H12B	0.9479	0.0530	0.0076	0.040*
C13	0.9149 (5)	0.14331 (13)	−0.0008 (3)	0.0346 (8)
H13A	1.0528	0.1506	−0.0258	0.042*
H13B	0.7997	0.1420	−0.0673	0.042*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0231 (4)	0.0290 (4)	0.0237 (4)	−0.0011 (3)	0.0024 (3)	−0.0009 (3)
O1W	0.0439 (13)	0.0327 (13)	0.0623 (16)	0.0011 (10)	0.0131 (12)	−0.0080 (11)
O1	0.0342 (11)	0.0457 (14)	0.0209 (12)	0.0003 (9)	−0.0027 (9)	0.0051 (9)
O2	0.0630 (16)	0.0310 (14)	0.0508 (16)	−0.0044 (11)	0.0049 (12)	0.0120 (11)
O3	0.0239 (11)	0.0606 (15)	0.0401 (14)	−0.0115 (10)	−0.0070 (10)	0.0122 (11)
O4	0.0416 (13)	0.0637 (17)	0.0469 (15)	0.0067 (12)	0.0196 (11)	−0.0167 (12)
N1	0.0267 (13)	0.0376 (16)	0.0275 (16)	−0.0033 (11)	0.0019 (12)	0.0095 (12)
N2	0.0327 (14)	0.0249 (15)	0.0230 (14)	−0.0041 (11)	−0.0036 (11)	0.0046 (11)
C1	0.0350 (16)	0.0349 (19)	0.0274 (17)	0.0063 (14)	0.0028 (13)	−0.0008 (14)
C2	0.0298 (15)	0.0218 (16)	0.0298 (17)	−0.0013 (12)	−0.0008 (13)	−0.0008 (13)
C3	0.0267 (14)	0.0203 (15)	0.0258 (16)	−0.0005 (12)	−0.0008 (12)	0.0047 (12)
C4	0.0401 (17)	0.0219 (17)	0.0266 (17)	−0.0035 (13)	0.0022 (14)	−0.0004 (13)
C5	0.0396 (18)	0.0320 (18)	0.0291 (18)	−0.0142 (14)	−0.0058 (14)	0.0019 (14)
C6	0.0318 (16)	0.0244 (17)	0.0326 (18)	0.0010 (12)	0.0047 (13)	0.0020 (13)
C7	0.0324 (15)	0.0227 (16)	0.0357 (18)	0.0010 (12)	0.0110 (13)	0.0020 (13)
C8	0.0347 (16)	0.0229 (17)	0.0379 (19)	0.0002 (13)	0.0094 (14)	−0.0012 (13)
C9	0.0325 (16)	0.0251 (17)	0.0317 (18)	0.0027 (12)	0.0051 (13)	0.0021 (13)
C10	0.0300 (15)	0.0235 (17)	0.0286 (17)	0.0016 (12)	0.0093 (13)	0.0005 (13)
C11	0.0272 (15)	0.0248 (17)	0.0275 (17)	0.0003 (12)	0.0058 (13)	0.0011 (12)
C12	0.0407 (17)	0.0243 (17)	0.0398 (19)	−0.0020 (13)	0.0206 (15)	−0.0047 (14)
C13	0.0391 (17)	0.0342 (19)	0.0324 (19)	−0.0038 (14)	0.0114 (15)	−0.0033 (14)

Geometric parameters (Å, º) top

S1—O2	1.459 (2)	C4—H4B	0.9700
S1—O1	1.469 (2)	C5—H5A	0.9700
S1—O4	1.477 (2)	C5—H5B	0.9700
S1—O3	1.478 (2)	C6—C7	1.530 (4)
O1W—H1WA	0.8501	C6—H6A	0.9700
O1W—H1WB	0.8500	C6—H6B	0.9700
N1—C1	1.478 (4)	C7—C8	1.525 (4)
N1—C5	1.489 (4)	C7—H7A	0.9700
N1—H1NA	0.94 (3)	C7—H7B	0.9700
N1—H1NB	0.85 (3)	C8—C11	1.524 (4)
N2—C13	1.488 (4)	C8—H8A	0.9700
N2—C9	1.497 (4)	C8—H8B	0.9700
N2—H2NA	0.88 (3)	C9—C10	1.509 (4)
N2—H2NB	0.92 (3)	C9—H9A	0.9700
C1—C2	1.515 (4)	C9—H9B	0.9700
C1—H1A	0.9700	C10—C11	1.526 (4)
C1—H1B	0.9700	C10—H10A	0.9700
C2—C3	1.534 (4)	C10—H10B	0.9700
C2—H2A	0.9700	C11—C12	1.527 (4)
C2—H2B	0.9700	C11—H11A	0.9800
C3—C6	1.523 (4)	C12—C13	1.509 (4)
C3—C4	1.534 (4)	C12—H12A	0.9700
C3—H3A	0.9800	C12—H12B	0.9700
C4—C5	1.516 (4)	C13—H13A	0.9700
C4—H4A	0.9700	C13—H13B	0.9700

O2—S1—O1	111.60 (13)	C3—C6—C7	115.3 (2)
O2—S1—O4	108.18 (14)	C3—C6—H6A	108.4
O1—S1—O4	110.38 (13)	C7—C6—H6A	108.4
O2—S1—O3	110.79 (13)	C3—C6—H6B	108.4
O1—S1—O3	108.13 (12)	C7—C6—H6B	108.4
O4—S1—O3	107.69 (14)	H6A—C6—H6B	107.5
H1WA—O1W—H1WB	100.7	C8—C7—C6	113.0 (2)
C1—N1—C5	112.5 (2)	C8—C7—H7A	109.0
C1—N1—H1NA	108.6 (19)	C6—C7—H7A	109.0
C5—N1—H1NA	112.1 (19)	C8—C7—H7B	109.0
C1—N1—H1NB	111 (2)	C6—C7—H7B	109.0
C5—N1—H1NB	106 (2)	H7A—C7—H7B	107.8
H1NA—N1—H1NB	107 (3)	C11—C8—C7	114.3 (2)
C13—N2—C9	112.4 (2)	C11—C8—H8A	108.7
C13—N2—H2NA	108 (2)	C7—C8—H8A	108.7
C9—N2—H2NA	110 (2)	C11—C8—H8B	108.7
C13—N2—H2NB	105.2 (19)	C7—C8—H8B	108.7
C9—N2—H2NB	109.9 (19)	H8A—C8—H8B	107.6
H2NA—N2—H2NB	111 (3)	N2—C9—C10	110.9 (2)
N1—C1—C2	111.3 (2)	N2—C9—H9A	109.4
N1—C1—H1A	109.4	C10—C9—H9A	109.4
C2—C1—H1A	109.4	N2—C9—H9B	109.4
N1—C1—H1B	109.4	C10—C9—H9B	109.4
C2—C1—H1B	109.4	H9A—C9—H9B	108.0
H1A—C1—H1B	108.0	C9—C10—C11	111.7 (2)
C1—C2—C3	113.0 (2)	C9—C10—H10A	109.3
C1—C2—H2A	109.0	C11—C10—H10A	109.3
C3—C2—H2A	109.0	C9—C10—H10B	109.3
C1—C2—H2B	109.0	C11—C10—H10B	109.3
C3—C2—H2B	109.0	H10A—C10—H10B	107.9
H2A—C2—H2B	107.8	C8—C11—C10	112.6 (2)
C6—C3—C2	112.0 (2)	C8—C11—C12	112.5 (2)
C6—C3—C4	110.4 (2)	C10—C11—C12	107.8 (2)
C2—C3—C4	109.0 (2)	C8—C11—H11A	107.9
C6—C3—H3A	108.5	C10—C11—H11A	107.9
C2—C3—H3A	108.5	C12—C11—H11A	107.9
C4—C3—H3A	108.5	C13—C12—C11	112.3 (2)
C5—C4—C3	112.1 (2)	C13—C12—H12A	109.2
C5—C4—H4A	109.2	C11—C12—H12A	109.2
C3—C4—H4A	109.2	C13—C12—H12B	109.2
C5—C4—H4B	109.2	C11—C12—H12B	109.2
C3—C4—H4B	109.2	H12A—C12—H12B	107.9
H4A—C4—H4B	107.9	N2—C13—C12	111.0 (2)
N1—C5—C4	109.9 (2)	N2—C13—H13A	109.4
N1—C5—H5A	109.7	C12—C13—H13A	109.4
C4—C5—H5A	109.7	N2—C13—H13B	109.4
N1—C5—H5B	109.7	C12—C13—H13B	109.4
C4—C5—H5B	109.7	H13A—C13—H13B	108.0
H5A—C5—H5B	108.2

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O4ⁱ	0.85	1.98	2.819 (3)	168
O1W—H1WB···O3ⁱⁱ	0.85	1.97	2.799 (3)	165
N1—H1NA···O4ⁱⁱⁱ	0.94 (3)	2.09 (3)	2.904 (3)	144 (3)
N1—H1NB···O3^iv	0.85 (3)	1.91 (3)	2.711 (3)	157 (3)
N2—H2NA···O1^v	0.88 (3)	1.83 (3)	2.704 (3)	177 (3)
N2—H2NB···O4^vi	0.92 (3)	2.02 (3)	2.845 (4)	149 (3)

Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x+3/2, y−1/2, −z+1/2; (iii) −x, −y, −z+1; (iv) −x+1, −y, −z+1; (v) x+1, y, z; (vi) x+1/2, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₂₈N₂²⁺·SO₄²⁻·H₂O
M_r	326.45
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	6.2019 (2), 22.5110 (5), 12.0052 (3)
β (°)	100.439 (2)
V (Å³)	1648.32 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.22 × 0.14 × 0.09

Data collection
Diffractometer	Siemens SMART 1K CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.927, 0.98
No. of measured, independent and observed [I > 2σ(I)] reflections	13022, 2932, 2011
R_int	0.066
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.131, 1.03
No. of reflections	2932
No. of parameters	202
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.40

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Bergerhoff et al., 1999), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O4ⁱ	0.85	1.98	2.819 (3)	168.3
O1W—H1WB···O3ⁱⁱ	0.85	1.97	2.799 (3)	164.9
N1—H1NA···O4ⁱⁱⁱ	0.94 (3)	2.09 (3)	2.904 (3)	144 (3)
N1—H1NB···O3^iv	0.85 (3)	1.91 (3)	2.711 (3)	157 (3)
N2—H2NA···O1^v	0.88 (3)	1.83 (3)	2.704 (3)	177 (3)
N2—H2NB···O4^vi	0.92 (3)	2.02 (3)	2.845 (4)	149 (3)

Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x+3/2, y−1/2, −z+1/2; (iii) −x, −y, −z+1; (iv) −x+1, −y, −z+1; (v) x+1, y, z; (vi) x+1/2, −y+1/2, z−1/2.

Acknowledgements

The authors acknowledge financial support from the Natural Science Foundation of Fujian Province (2006 F3042).

References

Bergerhoff, G., Berndt, M. & Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar