Dimethano­lbis[N′-(3-pyridylmethyl­ene)benzohydrazide]sodium(I) iodide

Cui, L.-S.; Yin, H.-D.; Yang, M.-L.; Wang, D.-Q.

doi:10.1107/S1600536808040750

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page m38

doi:10.1107/S1600536808040750

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Dimethanolbis[N′-(3-pyridylmethylene)benzohydrazide]sodium(I) iodide

Lian-Sheng Cui,^a Han-Dong Yin,^a ^* Ming-Lei Yang ^a and Da-Qi Wang ^a

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: handongyin@163.com

(Received 14 November 2008; accepted 3 December 2008; online 10 December 2008)

The molecule of the title compound, [Na(C₁₃H₁₁N₃O)₂(CH₃OH)₂]I, is non-planar, with the Na atom chelated by the O atoms and the N atoms of two N′-(3-pyridylmethylene)benzohydrazide ligands and both O atoms of two methanol ligands. The asymmetric unit consists of one half-molecule. The Na atom is located on a crystallographic centre of inversion. The six-coordinate Na atom adopts a distorted octahedral coordination. In the crystal structure, intermolecular N—H⋯I and O—H⋯N hydrogen bonds link the molecules into a two-dimensional network.

Related literature

For general background, see: Lindoy et al. (1976 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

[Na(C₁₃H₁₁N₃O)₂(CH₄O)₂]I
M_r = 664.47
Monoclinic, P 2₁ /n
a = 8.6078 (15) Å
b = 13.1842 (16) Å
c = 13.2508 (17) Å
β = 101.6540 (10)°
V = 1472.8 (4) Å³
Z = 2
Mo Kα radiation
μ = 1.15 mm⁻¹
T = 298 (2) K
0.54 × 0.43 × 0.40 mm

Data collection

Bruker SMART CCD area detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.577, T_max = 0.657
7140 measured reflections
2586 independent reflections
1919 reflections with I > 2σ(I)
R_int = 0.078

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.104
S = 1.05
2586 reflections
185 parameters
H-atom parameters constrained
Δρ_max = 0.69 e Å⁻³
Δρ_min = −0.87 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Na1—O1	2.294 (3)
Na1—O2	2.344 (2)
Na1—N2	2.642 (3)

O1—Na1—O2	86.74 (10)
O1—Na1—N2	65.34 (9)
O2—Na1—N2	88.40 (9)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯I1ⁱ	0.86	3.03	3.816 (3)	153
O2—H2⋯N3ⁱⁱ	0.82	1.98	2.792 (5)	171
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808040750/at2678sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808040750/at2678Isup2.hkl

checkCIF report

Comment top

Schiff bases have been known as effective ligands for metal ions in the preparation of dyes for many years, liquid crystals and powerful corrosion inhibitors. Furthermore, they are used in the mechanism of many biochemical processes (Lindoy et al., 1976). We report here the synthesis and crystal structure of the title compound (I).

The molecular structure of (I) is shown in Fig.1. The values of the geometric parameters in (I) are normal (Allen et al., 1987) (Table 1). In the crystal structure, there exist two intermolecular N—H···I and O—H···N hydrogen bonds (Table 2). As seen in Fig.2, the molecules are linked into two-dimensional network.

Related literature top

For general background, see: Lindoy et al. (1976). For bond-length data, see: Allen et al. (1987).

Experimental top

A mixture of N'-(3-pyridylmethylene)benzohydrazide (3 mmol) and sodium methoxide (3 mmol) and bismuth iodide(1 mmol) in absolute ethanol (15 ml) was heated under reflux with stirring for 5 h and then filtered.The resulting clear colourless solution was diffused diethyl ether vapor at room temperature for 16 days, after which large colourless block-shaped crystals of the title complex suitable for X-ray diffraction analysis were obtained.

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008.

Figures top

	Fig. 1. The structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The crystal packing of the title compound, viewed approximately along the c axis.

Dimethanolbis[N'-(3-pyridylmethylene)benzohydrazide]sodium(I) iodide top

Crystal data top

[Na(C₁₃H₁₁N₃O)₂(CH₄O)₂]I	F(000) = 672.0
M_r = 664.47	D_x = 1.494 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3137 reflections
a = 8.6078 (15) Å	θ = 2.2–27.2°
b = 13.1842 (16) Å	µ = 1.15 mm⁻¹
c = 13.2508 (17) Å	T = 298 K
β = 101.654 (1)°	Block, colourless
V = 1472.8 (4) Å³	0.54 × 0.43 × 0.40 mm
Z = 2

Data collection top

Bruker SMART CCD area detector diffractometer	2586 independent reflections
Radiation source: fine-focus sealed tube	1919 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.078
phi and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→9
T_min = 0.577, T_max = 0.657	k = −15→12
7140 measured reflections	l = −15→15

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.104	w = 1/[σ²(F_o²) + (0.028P)² + 0.7317P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2586 reflections	Δρ_max = 0.69 e Å⁻³
185 parameters	Δρ_min = −0.87 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0258 (18)

Crystal data top

[Na(C₁₃H₁₁N₃O)₂(CH₄O)₂]I	V = 1472.8 (4) Å³
M_r = 664.47	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.6078 (15) Å	µ = 1.15 mm⁻¹
b = 13.1842 (16) Å	T = 298 K
c = 13.2508 (17) Å	0.54 × 0.43 × 0.40 mm
β = 101.654 (1)°

Data collection top

Bruker SMART CCD area detector diffractometer	2586 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1919 reflections with I > 2σ(I)
T_min = 0.577, T_max = 0.657	R_int = 0.078
7140 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.05	Δρ_max = 0.69 e Å⁻³
2586 reflections	Δρ_min = −0.87 e Å⁻³
185 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
Na1	0.5000	0.5000	0.0000	0.0383 (5)
I1	0.0000	0.5000	0.5000	0.0439 (2)
N1	0.6395 (4)	0.2735 (2)	0.0500 (2)	0.0384 (8)
H1	0.6445	0.2085	0.0462	0.046*
N2	0.5180 (3)	0.3195 (2)	0.0883 (2)	0.0347 (7)
N3	0.0867 (4)	0.2404 (3)	0.2536 (3)	0.0470 (9)
O1	0.7451 (3)	0.42504 (19)	0.0231 (2)	0.0480 (7)
O2	0.4427 (3)	0.4186 (2)	−0.16052 (19)	0.0492 (7)
H2	0.4879	0.3694	−0.1793	0.074*
C1	0.7503 (4)	0.3326 (3)	0.0187 (3)	0.0336 (8)
C2	0.8797 (4)	0.2795 (3)	−0.0193 (3)	0.0319 (8)
C3	0.8939 (5)	0.1758 (3)	−0.0264 (3)	0.0455 (10)
H3	0.8179	0.1337	−0.0075	0.055*
C4	1.0197 (6)	0.1342 (3)	−0.0613 (3)	0.0564 (12)
H4	1.0281	0.0641	−0.0654	0.068*
C5	1.1334 (5)	0.1946 (4)	−0.0902 (3)	0.0526 (11)
H5	1.2187	0.1658	−0.1131	0.063*
C6	1.1193 (5)	0.2980 (3)	−0.0848 (3)	0.0498 (11)
H6	1.1948	0.3398	−0.1048	0.060*
C7	0.9930 (4)	0.3401 (3)	−0.0497 (3)	0.0424 (9)
H7	0.9842	0.4103	−0.0465	0.051*
C8	0.4330 (5)	0.2585 (3)	0.1286 (3)	0.0382 (9)
H8	0.4564	0.1895	0.1299	0.046*
C9	0.2103 (5)	0.2198 (3)	0.2102 (3)	0.0434 (10)
H9	0.2379	0.1522	0.2045	0.052*
C10	0.3003 (4)	0.2933 (3)	0.1730 (3)	0.0329 (8)
C11	0.2568 (5)	0.3933 (3)	0.1804 (3)	0.0439 (10)
H11	0.3129	0.4450	0.1561	0.053*
C12	0.1293 (5)	0.4150 (3)	0.2242 (3)	0.0487 (10)
H12	0.0978	0.4819	0.2299	0.058*
C13	0.0492 (5)	0.3378 (3)	0.2592 (3)	0.0471 (10)
H13	−0.0368	0.3542	0.2887	0.057*
C14	0.3307 (7)	0.4569 (4)	−0.2446 (3)	0.0740 (15)
H14A	0.2857	0.5185	−0.2245	0.111*
H14B	0.2481	0.4078	−0.2655	0.111*
H14C	0.3821	0.4705	−0.3011	0.111*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Na1	0.0414 (12)	0.0344 (12)	0.0424 (11)	0.0097 (9)	0.0161 (9)	−0.0003 (9)
I1	0.0536 (3)	0.0320 (3)	0.0480 (3)	0.00088 (16)	0.01502 (17)	−0.00036 (16)
N1	0.0429 (19)	0.0277 (16)	0.0514 (19)	0.0058 (14)	0.0258 (16)	−0.0028 (14)
N2	0.0336 (17)	0.0352 (17)	0.0395 (17)	0.0050 (14)	0.0178 (14)	−0.0020 (13)
N3	0.046 (2)	0.054 (2)	0.047 (2)	−0.0037 (17)	0.0229 (17)	0.0043 (16)
O1	0.0430 (16)	0.0313 (15)	0.0748 (19)	0.0031 (12)	0.0237 (14)	−0.0019 (13)
O2	0.0611 (19)	0.0450 (17)	0.0432 (15)	0.0100 (14)	0.0145 (14)	−0.0067 (13)
C1	0.033 (2)	0.033 (2)	0.0365 (19)	0.0057 (17)	0.0096 (16)	0.0026 (16)
C2	0.034 (2)	0.033 (2)	0.0294 (18)	0.0052 (17)	0.0082 (15)	−0.0014 (15)
C3	0.057 (3)	0.035 (2)	0.052 (2)	0.0053 (19)	0.028 (2)	0.0038 (18)
C4	0.067 (3)	0.044 (3)	0.067 (3)	0.018 (2)	0.035 (2)	0.002 (2)
C5	0.044 (3)	0.069 (3)	0.050 (3)	0.013 (2)	0.024 (2)	−0.006 (2)
C6	0.041 (2)	0.064 (3)	0.048 (2)	−0.006 (2)	0.020 (2)	−0.003 (2)
C7	0.042 (2)	0.040 (2)	0.047 (2)	−0.0017 (19)	0.0153 (18)	0.000 (2)
C8	0.044 (2)	0.032 (2)	0.042 (2)	0.0015 (17)	0.0164 (19)	0.0000 (16)
C9	0.053 (3)	0.037 (2)	0.044 (2)	−0.004 (2)	0.0186 (19)	0.0010 (19)
C10	0.031 (2)	0.039 (2)	0.0303 (18)	−0.0002 (17)	0.0116 (15)	0.0001 (16)
C11	0.054 (3)	0.037 (2)	0.048 (2)	−0.0022 (19)	0.027 (2)	−0.0001 (18)
C12	0.056 (3)	0.039 (2)	0.058 (3)	0.004 (2)	0.030 (2)	−0.005 (2)
C13	0.041 (2)	0.063 (3)	0.042 (2)	0.001 (2)	0.0216 (18)	−0.003 (2)
C14	0.095 (4)	0.076 (3)	0.049 (3)	0.012 (3)	0.009 (3)	0.007 (3)

Geometric parameters (Å, º) top

Na1—O1	2.294 (3)	C4—C5	1.375 (6)
Na1—O1ⁱ	2.294 (3)	C4—H4	0.9300
Na1—O2ⁱ	2.344 (2)	C5—C6	1.371 (6)
Na1—O2	2.344 (2)	C5—H5	0.9300
Na1—N2	2.642 (3)	C6—C7	1.382 (5)
Na1—N2ⁱ	2.642 (3)	C6—H6	0.9300
Na1—C1ⁱ	3.059 (4)	C7—H7	0.9300
N1—C1	1.360 (4)	C8—C10	1.461 (5)
N1—N2	1.390 (4)	C8—H8	0.9300
N1—H1	0.8600	C9—C10	1.391 (5)
N2—C8	1.276 (5)	C9—H9	0.9300
N3—C13	1.330 (5)	C10—C11	1.379 (5)
N3—C9	1.335 (5)	C11—C12	1.371 (5)
O1—C1	1.222 (4)	C11—H11	0.9300
O2—C14	1.412 (5)	C12—C13	1.362 (6)
O2—H2	0.8200	C12—H12	0.9300
C1—C2	1.487 (5)	C13—H13	0.9300
C2—C3	1.377 (5)	C14—H14A	0.9600
C2—C7	1.382 (5)	C14—H14B	0.9600
C3—C4	1.375 (6)	C14—H14C	0.9600
C3—H3	0.9300

O1—Na1—O1ⁱ	180.0	C4—C3—H3	119.8
O1—Na1—O2ⁱ	93.26 (10)	C2—C3—H3	119.8
O1ⁱ—Na1—O2ⁱ	86.74 (10)	C3—C4—C5	121.1 (4)
O1—Na1—O2	86.74 (10)	C3—C4—H4	119.5
O1ⁱ—Na1—O2	93.26 (10)	C5—C4—H4	119.5
O2ⁱ—Na1—O2	180.0	C6—C5—C4	119.0 (4)
O1—Na1—N2	65.34 (9)	C6—C5—H5	120.5
O1ⁱ—Na1—N2	114.66 (9)	C4—C5—H5	120.5
O2ⁱ—Na1—N2	91.60 (9)	C5—C6—C7	120.0 (4)
O2—Na1—N2	88.40 (9)	C5—C6—H6	120.0
O1—Na1—N2ⁱ	114.66 (9)	C7—C6—H6	120.0
O1ⁱ—Na1—N2ⁱ	65.34 (9)	C2—C7—C6	121.0 (4)
O2ⁱ—Na1—N2ⁱ	88.40 (9)	C2—C7—H7	119.5
O2—Na1—N2ⁱ	91.60 (9)	C6—C7—H7	119.5
N2—Na1—N2ⁱ	180.00 (6)	N2—C8—C10	122.1 (3)
O1—Na1—C1ⁱ	159.30 (9)	N2—C8—H8	118.9
O1ⁱ—Na1—C1ⁱ	20.70 (9)	C10—C8—H8	118.9
O2ⁱ—Na1—C1ⁱ	76.04 (9)	N3—C9—C10	124.1 (4)
O2—Na1—C1ⁱ	103.96 (9)	N3—C9—H9	118.0
N2—Na1—C1ⁱ	131.53 (9)	C10—C9—H9	118.0
N2ⁱ—Na1—C1ⁱ	48.47 (9)	C11—C10—C9	117.5 (3)
C1—N1—N2	119.1 (3)	C11—C10—C8	125.1 (3)
C1—N1—H1	120.4	C9—C10—C8	117.4 (3)
N2—N1—H1	120.4	C12—C11—C10	118.8 (4)
C8—N2—N1	114.5 (3)	C12—C11—H11	120.6
C8—N2—Na1	140.1 (3)	C10—C11—H11	120.6
N1—N2—Na1	102.3 (2)	C13—C12—C11	119.4 (4)
C13—N3—C9	116.3 (3)	C13—C12—H12	120.3
C1—O1—Na1	117.7 (2)	C11—C12—H12	120.3
C14—O2—Na1	122.5 (3)	N3—C13—C12	123.9 (4)
C14—O2—H2	109.5	N3—C13—H13	118.0
Na1—O2—H2	127.7	C12—C13—H13	118.0
O1—C1—N1	121.5 (3)	O2—C14—H14A	109.5
O1—C1—C2	121.5 (3)	O2—C14—H14B	109.5
N1—C1—C2	117.0 (3)	H14A—C14—H14B	109.5
C3—C2—C7	118.4 (3)	O2—C14—H14C	109.5
C3—C2—C1	125.0 (3)	H14A—C14—H14C	109.5
C7—C2—C1	116.6 (3)	H14B—C14—H14C	109.5
C4—C3—C2	120.4 (4)

C1—N1—N2—C8	−170.8 (3)	N2—N1—C1—C2	178.6 (3)
C1—N1—N2—Na1	25.1 (3)	O1—C1—C2—C3	179.9 (4)
O1—Na1—N2—C8	175.8 (4)	N1—C1—C2—C3	1.0 (5)
O1ⁱ—Na1—N2—C8	−4.2 (4)	O1—C1—C2—C7	−0.2 (5)
O2ⁱ—Na1—N2—C8	82.9 (4)	N1—C1—C2—C7	−179.1 (3)
O2—Na1—N2—C8	−97.1 (4)	C7—C2—C3—C4	1.1 (6)
C1ⁱ—Na1—N2—C8	10.2 (4)	C1—C2—C3—C4	−179.0 (4)
O1—Na1—N2—N1	−27.19 (19)	C2—C3—C4—C5	−0.3 (6)
O1ⁱ—Na1—N2—N1	152.81 (19)	C3—C4—C5—C6	−0.6 (7)
O2ⁱ—Na1—N2—N1	−120.0 (2)	C4—C5—C6—C7	0.6 (6)
O2—Na1—N2—N1	60.0 (2)	C3—C2—C7—C6	−1.1 (6)
C1ⁱ—Na1—N2—N1	167.28 (18)	C1—C2—C7—C6	179.1 (4)
O2ⁱ—Na1—O1—C1	122.2 (3)	C5—C6—C7—C2	0.2 (6)
O2—Na1—O1—C1	−57.8 (3)	N1—N2—C8—C10	179.9 (3)
N2—Na1—O1—C1	31.9 (3)	Na1—N2—C8—C10	−24.9 (6)
N2ⁱ—Na1—O1—C1	−148.1 (3)	C13—N3—C9—C10	0.9 (6)
C1ⁱ—Na1—O1—C1	180.0	N3—C9—C10—C11	−1.0 (6)
O1—Na1—O2—C14	−153.5 (3)	N3—C9—C10—C8	179.3 (4)
O1ⁱ—Na1—O2—C14	26.5 (3)	N2—C8—C10—C11	−2.9 (6)
N2—Na1—O2—C14	141.2 (3)	N2—C8—C10—C9	176.7 (4)
N2ⁱ—Na1—O2—C14	−38.8 (3)	C9—C10—C11—C12	0.5 (5)
C1ⁱ—Na1—O2—C14	8.6 (4)	C8—C10—C11—C12	−179.9 (4)
Na1—O1—C1—N1	−32.3 (4)	C10—C11—C12—C13	0.0 (6)
Na1—O1—C1—C2	148.9 (3)	C9—N3—C13—C12	−0.3 (6)
N2—N1—C1—O1	−0.3 (5)	C11—C12—C13—N3	−0.1 (7)

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···I1ⁱⁱ	0.86	3.03	3.816 (3)	153
O2—H2···N3ⁱⁱⁱ	0.82	1.98	2.792 (5)	171

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

Experimental details

Crystal data
Chemical formula	[Na(C₁₃H₁₁N₃O)₂(CH₄O)₂]I
M_r	664.47
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	8.6078 (15), 13.1842 (16), 13.2508 (17)
β (°)	101.654 (1)
V (Å³)	1472.8 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.15
Crystal size (mm)	0.54 × 0.43 × 0.40

Data collection
Diffractometer	Bruker SMART CCD area detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.577, 0.657
No. of measured, independent and observed [I > 2σ(I)] reflections	7140, 2586, 1919
R_int	0.078
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.104, 1.05
No. of reflections	2586
No. of parameters	185
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.69, −0.87

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008.

Selected geometric parameters (Å, º) top

Na1—O1	2.294 (3)	Na1—N2	2.642 (3)
Na1—O2	2.344 (2)

O1—Na1—O2	86.74 (10)	O2—Na1—N2	88.40 (9)
O1—Na1—N2	65.34 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···I1ⁱ	0.86	3.03	3.816 (3)	153
O2—H2···N3ⁱⁱ	0.82	1.98	2.792 (5)	171

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

Acknowledgements

We acknowledge the National Natural Science Foundation of China (grant No. 20771053), Shandong Province Science Foundation and the State Key Laboratory of Crystalline Materials, Shandong University.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Lindoy, L. F., Lip, H. C., Power, L. F. & Rea, T. H. (1976). Inorg. Chem. 15, 1724–1727. CrossRef CAS Web of Science 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