3,4,7,8-Tetra­methyl-1,10-phenanthrolin-1-ium nitrate monohydrate

Zhang, K.-J.; Zhang, Y.-F.

doi:10.1107/S1600536812023318

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 6| June 2012| Pages o1931-o1932

doi:10.1107/S1600536812023318

Open

access

3,4,7,8-Tetramethyl-1,10-phenanthrolin-1-ium nitrate monohydrate

Ke-Jie Zhang ^a ^* and Yan-Fang Zhang ^b

^aSchool of Material Science and Engineering, Nanjing Institute of Science and Technology, Nanjing 211168, People's Republic of China, and ^bDepartment of Life Science and Technology, Xinxiang College, Xinxiang 453003, People's Republic of China
^*Correspondence e-mail: xxzhangyanfang@126.com

(Received 10 May 2012; accepted 21 May 2012; online 31 May 2012)

In the crystal of the title compound, C₁₆H₁₇N₂⁺·NO₃⁻·H₂O, the tetramethyl-1,10-phenanthrolinium cations, nitrate anions and lattice water molecules are all located on a mirror plane with the methyl H atoms of the cation equally disordered over two sites about the mirror plane. The cation, anion and water molecule are linked by O—H⋯O and N—H⋯O hydrogen bonds into a sheet parallel to the bc plane. π–π stacking between phenanthroline ring systems is observed in the crystal structure, the centroid–centroid distance being 3.4745 (6) Å.

Related literature

For proton-transfer structures of phenanthroline and its derivatives, see: Bei et al. (2004 ); Buttery et al. (2006 ); Gillard et al. (1998 ); Harvey et al. (2008 ); Hensen et al. (1998 , 2000 ); Kolev et al. (2009 ); Lin et al. (2009 ); Maresca et al. (1989 ); Milani et al. (1997 ); Montagu-Bourin et al. (1981 ); Shang et al. (2006 ); Thevenet & Rodier (1978 ); Thevenet et al. (1977 , 1978 , 1980 ); Wang et al. (1999 ); Yu et al. (2006 ).

Experimental

Crystal data

C₁₆H₁₇N₂⁺·NO₃⁻·H₂O
M_r = 317.34
Orthorhombic, C m c a
a = 6.7401 (8) Å
b = 24.090 (3) Å
c = 19.254 (2) Å
V = 3126.1 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.37 × 0.30 × 0.21 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
11308 measured reflections
1585 independent reflections
1149 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.153
S = 1.03
1585 reflections
143 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O4ⁱ	0.86	1.86	2.692 (3)	164
O4—H1W⋯O1ⁱⁱ	0.84	1.97	2.808 (4)	174
O4—H2W⋯O1ⁱⁱⁱ	0.83	2.07	2.886 (4)	170
Symmetry codes: (i) x+1, y, z; (ii) $[x-{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (iii) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ .

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812023318/xu5537sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812023318/xu5537Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812023318/xu5537Isup3.cml

checkCIF report

Comment top

1,10-Phenanthroline and its derivatives have been recognized as good proton acceptors, and usually are considered a suitable agent in the synthesis of proton-transfer systems. Some proton-transfer complexes based on 1,10-phenanthroline (Buttery et al. 2006; Gillard et al. 1998; Hensen et al. 1998, 2000; Kolev et al. 2009; Maresca et al. 1989; Milani et al. 1997; Montagu-Bourin, Levillain, Ceolin, Thevenet & Souleau 1981; Shang et al. 2006; Thevenet & Rodier 1978; Thevenet et al. 1977, 1980; Thevenet, Rodier & Khodadad 1978; Wang et al. 1999), 2,9-dimethyl-1,10-phenanthroline (Harvey et al. 2008; Yu et al. 2006), and 6-nitro-1,10-phenanthroline (Bei et al. 2004), 5,6-dihydroxy-phenanthroline (Lin et al. 2009) have been synthesized. In the recent work, the title compound (I), C₁₆H₁₇N₂]NO₃.H₂O, was obtained unintentionally as a major product in the reaction of Tb(NO₃)₃.6H₂O with the 3,4,7,8-tetramethyl-1,10-phenanthroline in water. To the best our knowledge, this is the first example of proton-transfer system containing 3,4,7,8-tetramethyl-1,10- 1,10-phenanthroline.

The numbering scheme of (I) is given in Fig. 1, and the selected bond lengths and bond angles are provided in the cif file. The crystal contains one protonated 3,4,7,8-tetramethyl-1,10- 1,10-phenanthroline cation, one nitrate anion and one water molecule. In the crystal structure, the cations, anions and water molecules are linked into two dimensional layers parallel to the bc plane by N—H···O and O—H···O hydrogen bonds (Table 1). Among them, N—H···O hydrogen bonds play a very important role in the formation of proton-transfer compounds. Additionally, the monoprotonated 3,4,7,8-tetramethyl-1,10- 1,10-phenanthroline cations are parallel to each other in the crystal packing, showing π-π interactions (Fig. 2); the centroid–centroid distance is 3.4745 (6) Å.

Related literature top

For proton-transfer structures of phenanthroline and its derivations, see: Bei et al. (2004); Buttery et al. (2006); Gillard et al. (1998); Harvey et al. (2008); Hensen et al. (1998, 2000); Kolev et al. (2009); Lin et al. (2009); Maresca et al. (1989); Milani et al. (1997); Montagu-Bourin et al. (1981); Shang et al. (2006); Thevenet & Rodier (1978); Thevenet et al. (1977, 1978, 1980); Wang et al. (1999); Yu et al. (2006).

Experimental top

A aqueous solution (12 ml) of Tb(NO₃)₃.6H₂O (1 mmol) and 3,4,7,8-tetramethyl-1,10-phenanthroline (1 mmol) was stirred. The mixture was then transferred to a 25-ml Teflon reactor and kept at 433 K for 3 d under autogenous pressure, and then cooled to room temperature at a rate of 10 K h^-1. Colorless crystals of the title compound were obtained.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. π-π interactions between the neighboring aromatic rings of the title compound. Aromatic hydrogen atoms and methyl groups have been omitted for clarity.

3,4,7,8-Tetramethyl-1,10-phenanthrolin-1-ium nitrate monohydrate top

Crystal data top

C₁₆H₁₇N₂⁺·NO₃⁻·H₂O	F(000) = 1344
M_r = 317.34	D_x = 1.349 Mg m⁻³
Orthorhombic, Cmca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2bc 2	Cell parameters from 2972 reflections
a = 6.7401 (8) Å	θ = 2.7–25.0°
b = 24.090 (3) Å	µ = 0.10 mm⁻¹
c = 19.254 (2) Å	T = 296 K
V = 3126.1 (6) Å³	Block, colorless
Z = 8	0.37 × 0.30 × 0.21 mm

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	1149 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.029
Graphite monochromator	θ_max = 25.5°, θ_min = 2.7°
ϕ and ω scans	h = −8→7
11308 measured reflections	k = −28→28
1585 independent reflections	l = −23→23

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.153	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0707P)² + 2.7655P] where P = (F_o² + 2F_c²)/3
1585 reflections	(Δ/σ)_max < 0.001
143 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₆H₁₇N₂⁺·NO₃⁻·H₂O	V = 3126.1 (6) Å³
M_r = 317.34	Z = 8
Orthorhombic, Cmca	Mo Kα radiation
a = 6.7401 (8) Å	µ = 0.10 mm⁻¹
b = 24.090 (3) Å	T = 296 K
c = 19.254 (2) Å	0.37 × 0.30 × 0.21 mm

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	1149 reflections with I > 2σ(I)
11308 measured reflections	R_int = 0.029
1585 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.153	H-atom parameters constrained
S = 1.03	Δρ_max = 0.22 e Å⁻³
1585 reflections	Δρ_min = −0.27 e Å⁻³
143 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	Occ. (<1)
C1	1.0000	0.19047 (14)	0.08694 (15)	0.0642 (9)
H1	1.0000	0.1825	0.0397	0.077*
C2	1.0000	0.24624 (14)	0.10669 (16)	0.0618 (8)
C3	1.0000	0.25954 (12)	0.17669 (16)	0.0550 (8)
C4	1.0000	0.21518 (11)	0.22551 (14)	0.0474 (7)
C5	1.0000	0.22191 (12)	0.29933 (15)	0.0517 (7)
H5	1.0000	0.2576	0.3177	0.062*
C6	1.0000	0.17823 (11)	0.34314 (14)	0.0520 (7)
H6	1.0000	0.1847	0.3908	0.062*
C7	1.0000	0.12218 (11)	0.31849 (13)	0.0485 (7)
C8	1.0000	0.07458 (12)	0.36186 (14)	0.0561 (8)
C9	1.0000	0.02213 (12)	0.33180 (16)	0.0635 (9)
C10	1.0000	0.01823 (12)	0.26008 (17)	0.0660 (9)
H10	1.0000	−0.0168	0.2396	0.079*
C11	1.0000	0.11486 (10)	0.24627 (14)	0.0483 (7)
C12	1.0000	0.16081 (12)	0.19900 (13)	0.0485 (7)
C13	1.0000	0.29005 (16)	0.05051 (19)	0.0890 (12)
H13A	1.0207	0.2728	0.0062	0.134*	0.50
H13B	1.1046	0.3162	0.0592	0.134*	0.50
H13C	0.8747	0.3090	0.0505	0.134*	0.50
C14	1.0000	0.31938 (13)	0.1996 (2)	0.0764 (10)
H14A	0.8712	0.3352	0.1918	0.115*	0.50
H14B	1.0972	0.3397	0.1734	0.115*	0.50
H14C	1.0316	0.3214	0.2481	0.115*	0.50
C15	1.0000	0.08170 (15)	0.43955 (15)	0.0770 (11)
H15A	0.9482	0.0488	0.4610	0.116*	0.50
H15B	0.9186	0.1129	0.4518	0.116*	0.50
H15C	1.1332	0.0880	0.4554	0.116*	0.50
C16	1.0000	−0.03134 (13)	0.3737 (2)	0.0912 (13)
H16A	1.0869	−0.0274	0.4129	0.137*	0.50
H16B	1.0453	−0.0614	0.3450	0.137*	0.50
H16C	0.8679	−0.0390	0.3896	0.137*	0.50
N1	1.0000	0.14820 (10)	0.13060 (11)	0.0570 (7)
N2	1.0000	0.06277 (9)	0.21952 (11)	0.0574 (7)
H2	1.0000	0.0585	0.1752	0.069*
N3	0.5000	0.38702 (12)	0.09781 (14)	0.0702 (8)
O1	0.5000	0.41620 (12)	0.04627 (14)	0.1338 (15)
O2	0.5000	0.40810 (14)	0.15514 (15)	0.1348 (15)
O3	0.5000	0.33707 (11)	0.09262 (15)	0.1115 (11)
O4	0.0000	0.02821 (10)	0.08654 (12)	0.1174 (13)
H2W	0.0000	0.0477	0.0512	0.176*
H1W	0.0000	−0.0058	0.0779	0.176*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.080 (2)	0.077 (2)	0.0361 (15)	0.000	0.000	0.0103 (14)
C2	0.066 (2)	0.067 (2)	0.0532 (18)	0.000	0.000	0.0177 (15)
C3	0.0574 (18)	0.0486 (16)	0.0589 (18)	0.000	0.000	0.0098 (13)
C4	0.0515 (16)	0.0464 (15)	0.0444 (15)	0.000	0.000	0.0003 (11)
C5	0.0607 (18)	0.0442 (15)	0.0501 (16)	0.000	0.000	−0.0088 (12)
C6	0.0679 (19)	0.0516 (16)	0.0365 (14)	0.000	0.000	−0.0074 (12)
C7	0.0616 (18)	0.0480 (15)	0.0360 (13)	0.000	0.000	−0.0022 (11)
C8	0.078 (2)	0.0541 (17)	0.0366 (14)	0.000	0.000	0.0036 (12)
C9	0.093 (2)	0.0498 (17)	0.0477 (17)	0.000	0.000	0.0039 (13)
C10	0.101 (3)	0.0448 (16)	0.0521 (18)	0.000	0.000	−0.0060 (13)
C11	0.0632 (18)	0.0475 (15)	0.0343 (13)	0.000	0.000	−0.0024 (11)
C12	0.0574 (17)	0.0528 (16)	0.0354 (13)	0.000	0.000	0.0007 (11)
C13	0.110 (3)	0.091 (3)	0.067 (2)	0.000	0.000	0.036 (2)
C14	0.091 (3)	0.055 (2)	0.083 (2)	0.000	0.000	0.0130 (17)
C15	0.125 (3)	0.070 (2)	0.0363 (15)	0.000	0.000	0.0060 (14)
C16	0.149 (4)	0.053 (2)	0.072 (2)	0.000	0.000	0.0145 (17)
N1	0.0772 (17)	0.0600 (14)	0.0338 (11)	0.000	0.000	0.0002 (10)
N2	0.0918 (19)	0.0467 (13)	0.0336 (11)	0.000	0.000	−0.0057 (10)
N3	0.095 (2)	0.0645 (18)	0.0508 (16)	0.000	0.000	−0.0033 (13)
O1	0.259 (5)	0.0823 (19)	0.0605 (16)	0.000	0.000	0.0153 (15)
O2	0.233 (4)	0.104 (2)	0.0669 (18)	0.000	0.000	−0.0228 (17)
O3	0.178 (3)	0.0621 (17)	0.095 (2)	0.000	0.000	0.0016 (15)
O4	0.238 (4)	0.0661 (15)	0.0483 (14)	0.000	0.000	−0.0128 (11)

Geometric parameters (Å, º) top

C1—N1	1.320 (4)	C11—N2	1.356 (3)
C1—C2	1.396 (5)	C11—C12	1.433 (4)
C1—H1	0.9300	C12—N1	1.351 (3)
C2—C3	1.385 (4)	C13—H13A	0.9600
C2—C13	1.511 (4)	C13—H13B	0.9600
C3—C4	1.423 (4)	C13—H13C	0.9600
C3—C14	1.508 (4)	C14—H14A	0.9600
C4—C12	1.406 (4)	C14—H14B	0.9600
C4—C5	1.431 (4)	C14—H14C	0.9600
C5—C6	1.349 (4)	C15—H15A	0.9600
C5—H5	0.9300	C15—H15B	0.9600
C6—C7	1.431 (4)	C15—H15C	0.9600
C6—H6	0.9300	C16—H16A	0.9600
C7—C11	1.402 (4)	C16—H16B	0.9600
C7—C8	1.419 (4)	C16—H16C	0.9600
C8—C9	1.390 (4)	N2—H2	0.8600
C8—C15	1.506 (4)	N3—O3	1.208 (4)
C9—C10	1.384 (5)	N3—O2	1.215 (4)
C9—C16	1.520 (4)	N3—O1	1.216 (4)
C10—N2	1.327 (4)	O4—H2W	0.8276
C10—H10	0.9300	O4—H1W	0.8365

N1—C1—C2	124.7 (3)	N1—C12—C11	116.4 (2)
N1—C1—H1	117.7	C4—C12—C11	119.3 (2)
C2—C1—H1	117.7	C2—C13—H13A	109.5
C3—C2—C1	119.2 (3)	C2—C13—H13B	109.5
C3—C2—C13	122.3 (3)	H13A—C13—H13B	109.5
C1—C2—C13	118.5 (3)	C2—C13—H13C	109.5
C2—C3—C4	118.0 (3)	H13A—C13—H13C	109.5
C2—C3—C14	120.4 (3)	H13B—C13—H13C	109.5
C4—C3—C14	121.7 (3)	C3—C14—H14A	109.5
C12—C4—C3	117.4 (2)	C3—C14—H14B	109.5
C12—C4—C5	117.8 (2)	H14A—C14—H14B	109.5
C3—C4—C5	124.8 (3)	C3—C14—H14C	109.5
C6—C5—C4	122.2 (3)	H14A—C14—H14C	109.5
C6—C5—H5	118.9	H14B—C14—H14C	109.5
C4—C5—H5	118.9	C8—C15—H15A	109.5
C5—C6—C7	121.9 (2)	C8—C15—H15B	109.5
C5—C6—H6	119.0	H15A—C15—H15B	109.5
C7—C6—H6	119.0	C8—C15—H15C	109.5
C11—C7—C8	118.8 (2)	H15A—C15—H15C	109.5
C11—C7—C6	116.6 (2)	H15B—C15—H15C	109.5
C8—C7—C6	124.6 (2)	C9—C16—H16A	109.5
C9—C8—C7	119.3 (2)	C9—C16—H16B	109.5
C9—C8—C15	121.2 (3)	H16A—C16—H16B	109.5
C7—C8—C15	119.5 (3)	C9—C16—H16C	109.5
C10—C9—C8	118.5 (3)	H16A—C16—H16C	109.5
C10—C9—C16	118.2 (3)	H16B—C16—H16C	109.5
C8—C9—C16	123.3 (3)	C1—N1—C12	116.5 (3)
N2—C10—C9	122.2 (3)	C10—N2—C11	121.6 (2)
N2—C10—H10	118.9	C10—N2—H2	119.2
C9—C10—H10	118.9	C11—N2—H2	119.2
N2—C11—C7	119.5 (2)	O3—N3—O2	119.4 (3)
N2—C11—C12	118.3 (2)	O3—N3—O1	120.6 (3)
C7—C11—C12	122.2 (2)	O2—N3—O1	120.0 (3)
N1—C12—C4	124.3 (2)	H2W—O4—H1W	113.2

N1—C1—C2—C3	0.0	C15—C8—C9—C16	0.0
N1—C1—C2—C13	180.0	C8—C9—C10—N2	0.0
C1—C2—C3—C4	0.0	C16—C9—C10—N2	180.0
C13—C2—C3—C4	180.0	C8—C7—C11—N2	0.0
C1—C2—C3—C14	180.0	C6—C7—C11—N2	180.0
C13—C2—C3—C14	0.0	C8—C7—C11—C12	180.0
C2—C3—C4—C12	0.0	C6—C7—C11—C12	0.0
C14—C3—C4—C12	180.0	C3—C4—C12—N1	0.0
C2—C3—C4—C5	180.0	C5—C4—C12—N1	180.0
C14—C3—C4—C5	0.0	C3—C4—C12—C11	180.0
C12—C4—C5—C6	0.0	C5—C4—C12—C11	0.0
C3—C4—C5—C6	180.0	N2—C11—C12—N1	0.0
C4—C5—C6—C7	0.0	C7—C11—C12—N1	180.0
C5—C6—C7—C11	0.0	N2—C11—C12—C4	180.0
C5—C6—C7—C8	180.0	C7—C11—C12—C4	0.0
C11—C7—C8—C9	0.0	C2—C1—N1—C12	0.0
C6—C7—C8—C9	180.0	C4—C12—N1—C1	0.0
C11—C7—C8—C15	180.0	C11—C12—N1—C1	180.0
C6—C7—C8—C15	0.0	C9—C10—N2—C11	0.0
C7—C8—C9—C10	0.0	C7—C11—N2—C10	0.0
C15—C8—C9—C10	180.0	C12—C11—N2—C10	180.0
C7—C8—C9—C16	180.0

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4ⁱ	0.86	1.86	2.692 (3)	164
O4—H1W···O1ⁱⁱ	0.84	1.97	2.808 (4)	174
O4—H2W···O1ⁱⁱⁱ	0.83	2.07	2.886 (4)	170

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₇N₂⁺·NO₃⁻·H₂O
M_r	317.34
Crystal system, space group	Orthorhombic, Cmca
Temperature (K)	296
a, b, c (Å)	6.7401 (8), 24.090 (3), 19.254 (2)
V (Å³)	3126.1 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.37 × 0.30 × 0.21

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	11308, 1585, 1149
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.153, 1.03
No. of reflections	1585
No. of parameters	143
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.27

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXTL (Sheldrick, 2008), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4ⁱ	0.86	1.86	2.692 (3)	163.7
O4—H1W···O1ⁱⁱ	0.84	1.97	2.808 (4)	173.5
O4—H2W···O1ⁱⁱⁱ	0.83	2.07	2.886 (4)	170.2

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

Acknowledgements

Financial support from the National Natural Science Foundation of Henan Educational Committee, China (2011 C550002) is gratefully acknowledged.

References

Bei, F.-L., Yang, X.-J., Lu, L.-D. & Wang, X. (2004). J. Mol. Struct. 689, 237–243. Web of Science CSD CrossRef CAS Google Scholar
Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Buttery, J. H., Effendy, Junk, P. C., Mutrofin, S.,Skelton, B. W., Whitaker, C. R., White, A. H. (2006). Z. Anorg. Allg. Chem. 632, 1326–1339. Web of Science CSD CrossRef CAS Google Scholar
Gillard, R. D., Hursthouse, M. B., Abdul Malik, K. M. & Paisey, S. (1998). J. Chem. Crystallogr. 28, 611–619. Web of Science CSD CrossRef CAS Google Scholar
Harvey, M. A., Baggio, S., Garland, M. T. & Baggio, R. (2008). Acta Cryst. C64, o489–o492. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hensen, K., Gebhardt, F. & Bolte, M. (1998). Acta Cryst. C54, 359–361. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Hensen, K., Spangenberg, B. & Bolte, M. (2000). Acta Cryst. C56, 208–210. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Kolev, T., Koleva, B. B., Nikolova, R., Seidel, R. W., Mayer-Figge, H., Spiteller, M. & Sheldrick, W. S. (2009). Spectrochim. Acta Part A, 73, 929–935. CrossRef Google Scholar
Lin, X.-Y., Tang, S.-J. & Wu, W.-S. (2009). Acta Cryst. E65, o2367. Web of Science CSD CrossRef IUCr Journals Google Scholar
Maresca, L., Natile, G. & Fanizzi, F. P. (1989). J. Am. Chem. Soc. 111, 1492–1493. CSD CrossRef CAS Web of Science Google Scholar
Milani, B., Anzilutti, A., Vicentini, L., Santi, A. S., o Zangrando, E., Geremia, S. & Mestroni, G. (1997). Organometallics, 16, 5064–5075. Google Scholar
Montagu-Bourin, M., Levillain, P., Ceolin, R., Thevenet, G. & Souleau, C. (1981). J. Appl. Cryst. 14, 63. CSD CrossRef Web of Science IUCr Journals Google Scholar
Shang, R.-L., Du, L. & Sun, B.-W. (2006). Acta Cryst. E62, o2920–o2921. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Thevenet, G. & Rodier, N. (1978). Acta Cryst. B34, 880–882. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Thevenet, G., Rodier, N. & Khodadad, P. (1978). Acta Cryst. B34, 2594–2599. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Thevenet, G., Souleau, C., Montagu-Bourin, M. & Ceolin, R. (1980). J. Appl. Cryst. 13, 315. CSD CrossRef IUCr Journals Web of Science Google Scholar
Thevenet, G., Toffoli, P., Rodier, N. & Céolin, R. (1977). Acta Cryst. B33, 2526–2529. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Wang, Y.-Q., Wang, Z.-M., Liao, C.-S. & Yan, C.-H. (1999). Acta Cryst. C55, 1503–1506. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yu, Y.-Q., Ding, C.-F., Zhang, M.-L., Li, X.-M. & Zhang, S.-S. (2006). Acta Cryst. E62, o2187–o2189. Web of Science CSD CrossRef IUCr Journals Google Scholar