Tris(3-amino­phen­yl)phosphine oxide ethanol solvate

Han, J.; Li, W.; Wang, S.; Jiang, J.

doi:10.1107/S160053680900909X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o839

doi:10.1107/S160053680900909X

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Tris(3-aminophenyl)phosphine oxide ethanol solvate

Jun Han,^a Wenguang Li,^b Shufang Wang ^b and Juli Jiang ^a ^*

^aKey Laboratory of Mesoscopic Chemistry of the Ministry of Education, and School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, People's Republic of China, and ^bJiangguantun Middle School, Liaocheng 252022, Shangdong Province, People's Republic of China
^*Correspondence e-mail: jjl@nju.edu.cn

(Received 19 February 2009; accepted 12 March 2009; online 25 March 2009)

The title compound crystallized as an ethanol solvate, C₁₈H₁₈N₃OP·C₂H₆O. It is the reduction product of tris(3-nitrophenyl)phosphine oxide. In the crystal, there are intermolecular N—H⋯O hydrogen bonds between neighbouring tris(3-aminophenyl)phosphine oxide molecules and O—H⋯O hydrogen bonds involving the ethanol solvent molecule.

Related literature

The structure of tris(3-nitrophenyl)phosphine oxide is described by Jean-Noël et al. (2004 ). For literature on related compounds, see: Michaelis et al. (1885 ); Dressick et al. (2000 ); Hessler & Stelzer (1997 ).

Experimental

Crystal data

C₁₈H₁₈N₃OP·C₂H₆O
M_r = 369.39
Triclinic, $[P \overline 1]$
a = 9.1046 (13) Å
b = 10.7595 (15) Å
c = 12.020 (3) Å
α = 109.131 (3)°
β = 94.245 (3)°
γ = 114.028 (2)°
V = 986.3 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.16 mm⁻¹
T = 293 K
0.35 × 0.34 × 0.30 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.947, T_max = 0.954
5014 measured reflections
3420 independent reflections
1659 reflections with I > 2σ(I)
R_int = 0.058

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.149
S = 0.85
3420 reflections
174 parameters
H-atom parameters constrained
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯N1ⁱ	0.86	2.62	3.469 (6)	168
N2—H2B⋯O1ⁱⁱ	0.86	2.14	2.987 (4)	168
N2—H2C⋯O2ⁱⁱⁱ	0.86	2.23	3.089 (5)	173
O2—H2⋯O1	0.82	1.85	2.672 (3)	178
Symmetry codes: (i) x-1, y-1, z; (ii) -x+1, -y+1, -z+1; (iii) x+1, y, z.

Data collection: SMART (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680900909X/pk2158sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680900909X/pk2158Isup2.hkl

checkCIF report

Comment top

Arylphosphines have been investigated extensively as ionic ligands for catalytically active transition metals in aqueous solution (Hessler & Stelzer, 1997), as starting materials for the molecular fabrication of materials (Dressick et al., 2000) and so on. As early as 1885, tris(3-aminophenyl)phosphine oxide had been synthesized in the Sn/HCl system but with low yield (Michaelis et al., 1885). The molecules of the title compound crystallized as an ethanol solvate (Fig. 1). Adjacent molecules are linked via intermolecular O—H···O and N—H···O interactions, such as O2—H2···O1, N2—H2B···O1, N2—H2C···O2 and N1—H1A···O2 from a neighboring molecule (Fig. 2).

Related literature top

The structure of tris(3-nitrophenyl)phosphine oxide is described by Jean-Noël et al. (2004). For literature on related compounds, see: Michaelis et al. (1885); Dressick et al. (2000); Hessler & Stelzer (1997).

Experimental top

The precursor, tris(3-nitrophenyl)phosphine oxide (1.032 g, 2.5 mmol), was added to a mixture of ethanol (30 ml), THF (30 ml), hydrazine hydrate (10 ml) and a catalytic amount of Raney Ni in a 100 ml flask. The mixture was heated to reflux and reaction progress was monitored by TLC. The pure product was obtained as colorless crystals suitable for X-ray analysis after removing most of the solvent and without further purification (yield > 99%).

Computing details top

Data collection: SMART (Bruker, 2005); cell refinement: SMART (Bruker, 2005); data reduction: SAINT (Bruker, 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

	Fig. 1. The molecular structure of the title compound with the atom-numbering scheme.
	Fig. 2. The crystal packing of the title compound, viewed along the a axis.

Tris(3-aminophenyl)phosphine oxide ethanol solvate top

Crystal data top

C₁₈H₁₈N₃OP·C₂H₆O	Z = 2
M_r = 369.39	F(000) = 392
Triclinic, P1	D_x = 1.244 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.1046 (13) Å	Cell parameters from 706 reflections
b = 10.7595 (15) Å	θ = 2.6–19.5°
c = 12.020 (3) Å	µ = 0.16 mm⁻¹
α = 109.131 (3)°	T = 293 K
β = 94.245 (3)°	Prism, colorless
γ = 114.028 (2)°	0.35 × 0.34 × 0.30 mm
V = 986.3 (3) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	3420 independent reflections
Radiation source: fine-focus sealed tube	1659 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.058
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −10→10
T_min = 0.947, T_max = 0.954	k = −11→12
5014 measured reflections	l = −14→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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.149	H-atom parameters constrained
S = 0.85	w = 1/[σ²(F_o²) + (0.0599P)²] where P = (F_o² + 2F_c²)/3
3420 reflections	(Δ/σ)_max < 0.001
174 parameters	Δρ_max = 0.53 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₁₈H₁₈N₃OP·C₂H₆O	γ = 114.028 (2)°
M_r = 369.39	V = 986.3 (3) Å³
Triclinic, P1	Z = 2
a = 9.1046 (13) Å	Mo Kα radiation
b = 10.7595 (15) Å	µ = 0.16 mm⁻¹
c = 12.020 (3) Å	T = 293 K
α = 109.131 (3)°	0.35 × 0.34 × 0.30 mm
β = 94.245 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3420 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1659 reflections with I > 2σ(I)
T_min = 0.947, T_max = 0.954	R_int = 0.058
5014 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.149	H-atom parameters constrained
S = 0.85	Δρ_max = 0.53 e Å⁻³
3420 reflections	Δρ_min = −0.41 e Å⁻³
174 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 > 2σ(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
P1	0.32847 (11)	0.46681 (10)	0.24048 (9)	0.040
O1	0.2533 (3)	0.4519 (2)	0.3452 (2)	0.048
O2	0.0137 (3)	0.2243 (3)	0.3724 (3)	0.0692 (9)
H2	0.0879	0.2929	0.3632	0.104*
C12	0.5751 (4)	0.7116 (4)	0.2172 (3)	0.0450 (9)
H12	0.6148	0.6475	0.1749	0.054*
C7	0.4373 (4)	0.6580 (4)	0.2618 (3)	0.0398 (9)
C1	0.1745 (4)	0.3739 (4)	0.0993 (3)	0.0430 (9)
C13	0.4720 (4)	0.3909 (3)	0.2210 (3)	0.0380 (9)
C17	0.6849 (4)	0.3539 (4)	0.3165 (3)	0.046
C11	0.6559 (4)	0.8607 (4)	0.2346 (3)	0.049
C18	0.5679 (4)	0.4064 (3)	0.3238 (3)	0.044
H18	0.5539	0.4528	0.3996	0.052*
N1	0.7909 (4)	0.9160 (4)	0.1905 (3)	0.076
H1A	0.8373	1.0081	0.2021	0.091*
H1B	0.8298	0.8588	0.1510	0.091*
C14	0.4895 (4)	0.3209 (4)	0.1081 (3)	0.048
H14	0.4243	0.3095	0.0387	0.058*
C16	0.7007 (4)	0.2837 (4)	0.2010 (3)	0.052
H16	0.7776	0.2472	0.1931	0.062*
C6	0.0464 (4)	0.2340 (4)	0.0766 (3)	0.0486 (10)
H6	0.0446	0.1908	0.1324	0.058*
C5	−0.0779 (4)	0.1596 (4)	−0.0291 (4)	0.057
C2	0.1779 (5)	0.4355 (4)	0.0146 (4)	0.0548 (11)
H2A	0.2642	0.5277	0.0288	0.066*
C10	0.5934 (5)	0.9530 (4)	0.2983 (4)	0.0592 (12)
H10	0.6457	1.0527	0.3111	0.071*
N2	0.7780 (4)	0.3664 (4)	0.4182 (3)	0.0764 (11)
H2B	0.7646	0.4074	0.4886	0.092*
H2C	0.8497	0.3332	0.4116	0.092*
C9	0.4574 (5)	0.9015 (4)	0.3424 (4)	0.0599 (11)
H9	0.4176	0.9657	0.3844	0.072*
C8	0.3784 (5)	0.7539 (4)	0.3248 (3)	0.0534 (10)
H8	0.2857	0.7189	0.3553	0.064*
C15	0.6044 (4)	0.2679 (4)	0.0989 (3)	0.056
H15	0.6170	0.2208	0.0228	0.068*
C3	0.0530 (5)	0.3608 (5)	−0.0918 (4)	0.0677 (13)
H3	0.0555	0.4027	−0.1486	0.081*
N3	−0.2044 (5)	0.0239 (4)	−0.0519 (4)	0.106
H3A	−0.2077	−0.0164	−0.0005	0.127*
H3B	−0.2811	−0.0214	−0.1178	0.127*
C4	−0.0726 (5)	0.2259 (5)	−0.1117 (4)	0.0687 (13)
H4	−0.1568	0.1768	−0.1822	0.082*
C20	0.0756 (6)	0.2038 (6)	0.4755 (5)	0.0963 (19)
H20A	0.1265	0.2969	0.5458	0.116*
H20B	−0.0150	0.1328	0.4941	0.116*
C19	0.1946 (8)	0.1515 (7)	0.4477 (6)	0.147 (3)
H19A	0.1414	0.0555	0.3825	0.221*
H19B	0.2426	0.1447	0.5180	0.221*
H19C	0.2800	0.2189	0.4239	0.221*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.041	0.039	0.040	0.017	0.012	0.016
O1	0.051	0.050	0.044	0.021	0.021	0.021
O2	0.0604 (18)	0.062 (2)	0.081 (2)	0.0167 (15)	0.0085 (17)	0.0396 (17)
C12	0.050 (2)	0.036 (2)	0.042 (2)	0.0173 (19)	0.0080 (19)	0.0098 (18)
C7	0.043 (2)	0.037 (2)	0.037 (2)	0.0159 (18)	0.0056 (18)	0.0149 (18)
C1	0.043 (2)	0.047 (2)	0.041 (2)	0.023 (2)	0.0107 (18)	0.0159 (19)
C13	0.041 (2)	0.030 (2)	0.039 (2)	0.0122 (17)	0.0108 (18)	0.0129 (17)
C17	0.054	0.046	0.040	0.025	0.012	0.016
C11	0.049	0.045	0.042	0.012	0.007	0.019
C18	0.049	0.039	0.042	0.023	0.013	0.011
N1	0.082	0.056	0.078	0.021	0.031	0.024
C14	0.061	0.057	0.040	0.038	0.016	0.021
C16	0.056	0.055	0.056	0.034	0.021	0.024
C6	0.041 (2)	0.048 (2)	0.053 (3)	0.018 (2)	0.012 (2)	0.019 (2)
C5	0.038	0.042	0.067	0.013	0.007	0.001
C2	0.051 (2)	0.058 (3)	0.052 (3)	0.021 (2)	0.007 (2)	0.022 (2)
C10	0.071 (3)	0.038 (2)	0.056 (3)	0.017 (2)	−0.001 (2)	0.017 (2)
N2	0.096 (3)	0.104 (3)	0.046 (2)	0.076 (2)	0.004 (2)	0.014 (2)
C9	0.068 (3)	0.049 (3)	0.056 (3)	0.030 (2)	0.004 (2)	0.011 (2)
C8	0.056 (2)	0.048 (3)	0.052 (3)	0.024 (2)	0.007 (2)	0.016 (2)
C15	0.073	0.064	0.042	0.039	0.020	0.021
C3	0.070 (3)	0.071 (3)	0.058 (3)	0.033 (3)	0.006 (3)	0.023 (3)
N3	0.089	0.071	0.110	0.009	−0.009	0.020
C4	0.062 (3)	0.076 (3)	0.057 (3)	0.035 (3)	−0.004 (2)	0.013 (3)
C20	0.072 (3)	0.072 (4)	0.140 (6)	0.024 (3)	0.002 (4)	0.054 (4)
C19	0.158 (6)	0.134 (6)	0.132 (6)	0.039 (5)	−0.018 (5)	0.077 (5)

Geometric parameters (Å, º) top

P1—O1	1.500 (2)	C6—C5	1.385 (5)
P1—C13	1.794 (3)	C6—H6	0.9300
P1—C7	1.799 (3)	C5—N3	1.362 (5)
P1—C1	1.799 (4)	C5—C4	1.393 (5)
O2—C20	1.441 (5)	C2—C3	1.394 (5)
O2—H2	0.8200	C2—H2A	0.9300
C12—C7	1.381 (5)	C10—C9	1.361 (5)
C12—C11	1.398 (5)	C10—H10	0.9300
C12—H12	0.9300	N2—H2B	0.8600
C7—C8	1.388 (5)	N2—H2C	0.8600
C1—C2	1.381 (5)	C9—C8	1.383 (5)
C1—C6	1.399 (5)	C9—H9	0.9300
C13—C14	1.376 (5)	C8—H8	0.9300
C13—C18	1.380 (4)	C15—H15	0.9300
C17—N2	1.370 (4)	C3—C4	1.361 (5)
C17—C18	1.390 (4)	C3—H3	0.9300
C17—C16	1.396 (5)	N3—H3A	0.8600
C11—N1	1.362 (4)	N3—H3B	0.8600
C11—C10	1.387 (5)	C4—H4	0.9300
C18—H18	0.9300	C20—C19	1.424 (8)
N1—H1A	0.8600	C20—H20A	0.9700
N1—H1B	0.8600	C20—H20B	0.9700
C14—C15	1.377 (5)	C19—H19A	0.9600
C14—H14	0.9300	C19—H19B	0.9600
C16—C15	1.372 (5)	C19—H19C	0.9600
C16—H16	0.9300

O1—P1—C13	112.04 (15)	N3—C5—C4	120.3 (4)
O1—P1—C7	110.89 (16)	C6—C5—C4	119.1 (4)
C13—P1—C7	107.89 (16)	C1—C2—C3	120.6 (4)
O1—P1—C1	112.16 (15)	C1—C2—H2A	119.7
C13—P1—C1	106.99 (16)	C3—C2—H2A	119.7
C7—P1—C1	106.60 (16)	C9—C10—C11	121.7 (4)
C20—O2—H2	109.5	C9—C10—H10	119.2
C7—C12—C11	121.1 (4)	C11—C10—H10	119.2
C7—C12—H12	119.5	C17—N2—H2B	120.0
C11—C12—H12	119.5	C17—N2—H2C	120.0
C12—C7—C8	119.3 (3)	H2B—N2—H2C	120.0
C12—C7—P1	122.6 (3)	C10—C9—C8	120.1 (4)
C8—C7—P1	118.1 (3)	C10—C9—H9	120.0
C2—C1—C6	119.5 (3)	C8—C9—H9	120.0
C2—C1—P1	122.8 (3)	C9—C8—C7	120.0 (4)
C6—C1—P1	117.7 (3)	C9—C8—H8	120.0
C14—C13—C18	120.2 (3)	C7—C8—H8	120.0
C14—C13—P1	122.0 (3)	C16—C15—C14	120.6 (4)
C18—C13—P1	117.8 (3)	C16—C15—H15	119.7
N2—C17—C18	121.5 (3)	C14—C15—H15	119.7
N2—C17—C16	121.0 (3)	C4—C3—C2	119.3 (4)
C18—C17—C16	117.5 (3)	C4—C3—H3	120.4
N1—C11—C10	120.0 (4)	C2—C3—H3	120.4
N1—C11—C12	122.2 (4)	C5—N3—H3A	120.0
C10—C11—C12	117.8 (4)	C5—N3—H3B	120.0
C13—C18—C17	121.3 (3)	H3A—N3—H3B	120.0
C13—C18—H18	119.4	C3—C4—C5	121.6 (4)
C17—C18—H18	119.4	C3—C4—H4	119.2
C11—N1—H1A	120.0	C5—C4—H4	119.2
C11—N1—H1B	120.0	C19—C20—O2	109.0 (5)
H1A—N1—H1B	120.0	C19—C20—H20A	109.9
C13—C14—C15	119.4 (3)	O2—C20—H20A	109.9
C13—C14—H14	120.3	C19—C20—H20B	109.9
C15—C14—H14	120.3	O2—C20—H20B	109.9
C15—C16—C17	121.0 (4)	H20A—C20—H20B	108.3
C15—C16—H16	119.5	C20—C19—H19A	109.5
C17—C16—H16	119.5	C20—C19—H19B	109.5
C5—C6—C1	120.0 (4)	H19A—C19—H19B	109.5
C5—C6—H6	120.0	C20—C19—H19C	109.5
C1—C6—H6	120.0	H19A—C19—H19C	109.5
N3—C5—C6	120.6 (4)	H19B—C19—H19C	109.5

C11—C12—C7—C8	0.0 (5)	N2—C17—C18—C13	−178.7 (3)
C11—C12—C7—P1	179.4 (3)	C16—C17—C18—C13	−0.6 (5)
O1—P1—C7—C12	148.9 (3)	C18—C13—C14—C15	−0.6 (5)
C13—P1—C7—C12	25.9 (3)	P1—C13—C14—C15	178.5 (3)
C1—P1—C7—C12	−88.7 (3)	N2—C17—C16—C15	178.3 (3)
O1—P1—C7—C8	−31.7 (3)	C18—C17—C16—C15	0.2 (5)
C13—P1—C7—C8	−154.7 (3)	C2—C1—C6—C5	−1.4 (5)
C1—P1—C7—C8	90.7 (3)	P1—C1—C6—C5	178.1 (3)
O1—P1—C1—C2	137.1 (3)	C1—C6—C5—N3	−179.3 (4)
C13—P1—C1—C2	−99.7 (3)	C1—C6—C5—C4	0.3 (6)
C7—P1—C1—C2	15.5 (4)	C6—C1—C2—C3	1.4 (6)
O1—P1—C1—C6	−42.5 (3)	P1—C1—C2—C3	−178.1 (3)
C13—P1—C1—C6	80.8 (3)	N1—C11—C10—C9	179.1 (3)
C7—P1—C1—C6	−164.0 (3)	C12—C11—C10—C9	−0.3 (6)
O1—P1—C13—C14	145.0 (3)	C11—C10—C9—C8	0.4 (6)
C7—P1—C13—C14	−92.6 (3)	C10—C9—C8—C7	−0.2 (6)
C1—P1—C13—C14	21.7 (3)	C12—C7—C8—C9	0.0 (5)
O1—P1—C13—C18	−35.8 (3)	P1—C7—C8—C9	−179.4 (3)
C7—P1—C13—C18	86.5 (3)	C17—C16—C15—C14	−0.1 (6)
C1—P1—C13—C18	−159.2 (3)	C13—C14—C15—C16	0.3 (5)
C7—C12—C11—N1	−179.3 (3)	C1—C2—C3—C4	−0.1 (6)
C7—C12—C11—C10	0.1 (5)	C2—C3—C4—C5	−1.0 (6)
C14—C13—C18—C17	0.8 (5)	N3—C5—C4—C3	−179.5 (4)
P1—C13—C18—C17	−178.4 (3)	C6—C5—C4—C3	1.0 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N1ⁱ	0.86	2.62	3.469 (6)	168
O2—H2···O1	0.82	1.85	2.672 (3)	178
N2—H2B···O1ⁱⁱ	0.86	2.14	2.987 (4)	168
N2—H2C···O2ⁱⁱⁱ	0.86	2.23	3.089 (5)	173

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₈N₃OP·C₂H₆O
M_r	369.39
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.1046 (13), 10.7595 (15), 12.020 (3)
α, β, γ (°)	109.131 (3), 94.245 (3), 114.028 (2)
V (Å³)	986.3 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.16
Crystal size (mm)	0.35 × 0.34 × 0.30

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.947, 0.954
No. of measured, independent and observed [I > 2σ(I)] reflections	5014, 3420, 1659
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.149, 0.85
No. of reflections	3420
No. of parameters	174
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.53, −0.41

Computer programs: SMART (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N1ⁱ	0.86	2.62	3.469 (6)	167.5
O2—H2···O1	0.82	1.85	2.672 (3)	178.3
N2—H2B···O1ⁱⁱ	0.86	2.14	2.987 (4)	168.4
N2—H2C···O2ⁱⁱⁱ	0.86	2.23	3.089 (5)	172.7

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

Acknowledgements

The authors gratefully acknowledge the financial support of the NSFC (grant No. 20602017), the Program for New Century Excellent Talents in University (grant No. NCET-07-0425) and the Natural Science Foundation of Jiangsu (grant No. BK 2008259).

References

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