Tetra­aqua­bis­(1,10-phenanthroline-κ2N,N′)strontium 5,5′-diazene­diyl­ditetra­zolide

Jiao, B.-J.; Ren, Y.-X.; Zhu, G.; Yan, Z.-J.; Liu, F.-R.

doi:10.1107/S1600536810039115

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Pages m1375-m1376

https://doi.org/10.1107/S1600536810039115

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Tetraaquabis(1,10-phenanthroline-κ²N,N′)strontium 5,5′-diazenediylditetrazolide

Bao-Juan Jiao,^a ^* Yi-Xia Ren,^b Gang Zhu,^a Zhi-Jun Yan ^a and Fu-Rong Liu ^a

^aDepartment of Chemistry and Chemical Engineering, Xi'an University of Arts and Science, Xi'an 710065, Shaanxi, People's Republic of China, and ^bCollege of Chemistry and Chemical Engineering, Yanan University, Yanan 716000, Shaanxi, People's Republic of China
^*Correspondence e-mail: jiaobaojuan@163.com

(Received 22 September 2010; accepted 30 September 2010; online 9 October 2010)

The title complex, [Sr(C₁₂H₈N₂)₂(H₂O)₄](C₂N₁₀), contains an [Sr(phen)₂(H₂O)₄]²⁺ cation (phen is 1,10-phenanthroline) and a 5,5′-diazenediylditetrazolide anion (site symmetry 2). The Sr²⁺ cation (site symmetry 2) is coordinated by four N atoms from two chelating phen and four water molecules. In the crystal structure, the water molecules and the N atoms in the tetrazolide rings form an extensive range of O—H⋯N hydrogen bonds which link the complex into a two-dimensional structure. An adjacent layer further yields a three-dimensional supramolecular network by offset face-to-face π–π stacking interactions of the phen ligands [with centroid–centroid distances of 3.915 (2) and 4.012 (2) Å]. The two bridging N atoms of the anion are equally disordered about the twofold rotation axis.

Related literature

Tetrazole compounds have been investigated as potential energy materials; see: Singh et al. (2006 ); Klapötke et al. (2009 ). In particular, complexes of tetrazole containing cations such as strontium, barium or copper are components for pyrotechnical mixtures (Hartdegen et al., 2009 ; Klapötke et al., 2008 ). Additionally, the 5,5′-azotetrazole with ten nitrogen atoms is predicted to be involved in the hydrogen-bonding motif to construct a supramolecule (Wang et al., 2009 ).

Experimental

Crystal data

[Sr(C₁₂H₈N₂)₂(H₂O)₄](C₂N₁₀)
M_r = 684.21
Monoclinic, C 2/c
a = 17.442 (3) Å
b = 10.8974 (17) Å
c = 16.189 (3) Å
β = 105.178 (2)°
V = 2969.8 (8) Å³
Z = 4
Mo Kα radiation
μ = 1.88 mm⁻¹
T = 296 K
0.25 × 0.20 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: empirical (using intensity measurements) (SADABS; Bruker, 2002 ) T_min = 0.652, T_max = 0.729
7165 measured reflections
2621 independent reflections
2226 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.069
S = 1.04
2621 reflections
204 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2B⋯N5ⁱ	0.85	2.08	2.885 (3)	158
O1—H1A⋯N4ⁱ	0.85	2.04	2.870 (2)	167
O2—H2A⋯N6ⁱⁱ	0.85	2.03	2.871 (3)	173
O1—H1B⋯N3	0.85	2.04	2.887 (3)	172
Symmetry codes: (i) -x+2, -y+1, -z; (ii) x, y-1, z.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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: https://doi.org/10.1107/S1600536810039115/jh2212sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810039115/jh2212Isup2.hkl

checkCIF report

Comment top

The high nitrogen content of tetrazole has led to investigation for their use as potential energy materials (Singh et al., 2006; Klapötke et al., 2009). Especially, complex of tetrazole containing cations like strontium, barium, or copper are sought components for pyrotechnical mixtures, by combination of the ligand and the colorantmetal cation (Hartdegen et al., 2009; Klapötke et al., 2008). Additionally, the 5,5'-azotetrazole with ten nitrogen atoms are predicted to be involved in the hydrogen bonds motif to construct supramolecule (Wang et al., 2009). Herein, we report the crystal structure of the title compound, [Sr(phen)₂(H₂O)₄][AT] (I), where phen = 1,10-phenanthroline and AT = 5,5'-diazenediylditetrazolide. The crystal structure of (I) consists of a discrete [Sr(phen)₂(H₂O)₄]²⁺ cation and one 5,5'-diazenediylditetrazolide anion. As illustrated in Figure 1, the Sr²⁺ ion is coordinated by eight atoms with four N atoms from two phen molecules and four O atoms from water molecules, giving to a quadrangular prism structure. The N7 atom in the 5,5'-diazenediylditetrazolide anion is positional disordered and the occupancy of N7 must be set to 0.5 to get rational structure model and thermal displacement parameters. Strong hydrogen bonds between the 5,5'-diazenediylditetrazolide anion and water molecules link neighboring [Sr(phen)₂(H₂O)₄]²⁺ cations, which giving to a two dimensional supramolecular layer, as shown in the Figure 2. Furthermore, the adjacent layers were form to a three dimensional supramolecular network, by the off-set face to face π-π stacking interactions of the phen molecules, with the centroid distance 3.915 and 4.012 Å.

Related literature top

Tetrazole compounds have been investigated as potential energy materials; see: Singh et al. (2006); Klapötke et al. (2009). In particular, complexes of tetrazole containing cations such as strontium, barium or copper are components for pyrotechnical mixtures (Hartdegen et al., 2009; Klapötke et al., 2008). Additionally, the 5,5'-azotetrazole with ten nitrogen atoms is predicted to be involved in the hydrogen-bonding motif to construct a supramolecule (Wang et al., 2009). [This section has been rewritten - pls check this is OK]

Experimental top

30 ml H₂O containing 2.0 mmol (0.6003 g) disodium 5,5'-azotetrazole pentahydrate was mixed with 30 ml e thanol containing 4.0 mmol (0.7929 g) 1,10-phenanthroline. 15 ml H₂O containing 2.0 mmol (0.5332 g) SrCl₂.6H₂O was added to the above mixture. Yellow single crystals were obtained from the mixture solution which was allowed to evaporate at the room temperature for two weeks.

Structure description top

Tetrazole compounds have been investigated as potential energy materials; see: Singh et al. (2006); Klapötke et al. (2009). In particular, complexes of tetrazole containing cations such as strontium, barium or copper are components for pyrotechnical mixtures (Hartdegen et al., 2009; Klapötke et al., 2008). Additionally, the 5,5'-azotetrazole with ten nitrogen atoms is predicted to be involved in the hydrogen-bonding motif to construct a supramolecule (Wang et al., 2009). [This section has been rewritten - pls check this is OK]

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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. View of (I), A view of structure (I) showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level and hydrogen atoms are omitted for clarity. The occupancies of N7, are equal to 0.5 [Symmtry codes: A 2 - x,y,1/2 - z].
	Fig. 2. View of the supramolecular layer structure of (I) formed by the hydrogen bonds. The dashed lines are hydrogen bonds. Displacement ellipsoids are drawn at the 30% probability. The phen molecules are omitted for clarity.

Tetraaquabis(1,10-phenanthroline-κ²N,N')strontium 5,5'-diazenediylditetrazolide top

Crystal data top

[Sr(C₁₂H₈N₂)₂(H₂O)₄](C₂N₁₀)	F(000) = 1392
M_r = 684.21	D_x = 1.530 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 17.442 (3) Å	Cell parameters from 3217 reflections
b = 10.8974 (17) Å	θ = 2.2–26.9°
c = 16.189 (3) Å	µ = 1.88 mm⁻¹
β = 105.178 (2)°	T = 296 K
V = 2969.8 (8) Å³	Block, yellow
Z = 4	0.25 × 0.20 × 0.18 mm

Data collection top

Bruker APEXII CCD diffractometer	2621 independent reflections
Radiation source: fine-focus sealed tube	2226 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
φ and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: empirical (using intensity measurements) (SADABS; Bruker, 2002)	h = −20→20
T_min = 0.652, T_max = 0.729	k = −12→11
7165 measured reflections	l = −19→16

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)] = 0.027	H-atom parameters constrained
wR(F²) = 0.069	w = 1/[σ²(F_o²) + (0.0334P)² + 1.6965P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2621 reflections	Δρ_max = 0.31 e Å⁻³
204 parameters	Δρ_min = −0.37 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0049 (3)

Crystal data top

[Sr(C₁₂H₈N₂)₂(H₂O)₄](C₂N₁₀)	V = 2969.8 (8) Å³
M_r = 684.21	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 17.442 (3) Å	µ = 1.88 mm⁻¹
b = 10.8974 (17) Å	T = 296 K
c = 16.189 (3) Å	0.25 × 0.20 × 0.18 mm
β = 105.178 (2)°

Data collection top

Bruker APEXII CCD diffractometer	2621 independent reflections
Absorption correction: empirical (using intensity measurements) (SADABS; Bruker, 2002)	2226 reflections with I > 2σ(I)
T_min = 0.652, T_max = 0.729	R_int = 0.026
7165 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	0 restraints
wR(F²) = 0.069	H-atom parameters constrained
S = 1.04	Δρ_max = 0.31 e Å⁻³
2621 reflections	Δρ_min = −0.37 e Å⁻³
204 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)
Sr1	1.0000	0.24389 (2)	0.2500	0.02718 (12)
N1	0.85008 (10)	0.34918 (17)	0.18410 (12)	0.0395 (4)
N2	0.85933 (10)	0.10403 (17)	0.21752 (11)	0.0372 (4)
N3	0.96163 (12)	0.64644 (18)	0.09038 (13)	0.0483 (5)
N4	0.94140 (12)	0.68916 (18)	0.01083 (12)	0.0443 (5)
N5	0.93980 (13)	0.80929 (19)	0.01267 (13)	0.0499 (5)
N6	0.95898 (14)	0.8474 (2)	0.09331 (15)	0.0580 (6)
C1	0.84222 (15)	0.4689 (2)	0.17143 (17)	0.0515 (6)
H1	0.8839	0.5192	0.1998	0.062*
C2	0.77523 (17)	0.5244 (3)	0.11807 (19)	0.0643 (8)
H2	0.7729	0.6091	0.1110	0.077*
C3	0.71337 (16)	0.4521 (3)	0.07654 (18)	0.0640 (8)
H3	0.6685	0.4872	0.0401	0.077*
C4	0.71751 (14)	0.3253 (3)	0.08878 (15)	0.0477 (6)
C5	0.65475 (15)	0.2429 (3)	0.04826 (18)	0.0628 (8)
H5	0.6094	0.2741	0.0102	0.075*
C6	0.65995 (15)	0.1226 (3)	0.06392 (17)	0.0609 (8)
H6	0.6183	0.0716	0.0365	0.073*
C7	0.72830 (13)	0.0706 (2)	0.12204 (15)	0.0461 (6)
C8	0.73506 (15)	−0.0545 (2)	0.14216 (17)	0.0551 (7)
H8	0.6943	−0.1082	0.1165	0.066*
C9	0.80122 (15)	−0.0976 (2)	0.19914 (17)	0.0534 (7)
H9	0.8061	−0.1802	0.2139	0.064*
C10	0.86160 (14)	−0.0145 (2)	0.23494 (16)	0.0457 (6)
H10	0.9067	−0.0448	0.2739	0.055*
C11	0.78741 (12)	0.2779 (2)	0.14439 (14)	0.0374 (5)
C12	0.79253 (12)	0.1478 (2)	0.16157 (13)	0.0356 (5)
C13	0.97136 (14)	0.7456 (2)	0.13849 (15)	0.0476 (6)
O1	1.01607 (10)	0.39982 (14)	0.13806 (9)	0.0463 (4)
O2	0.98909 (9)	0.10539 (13)	0.11891 (9)	0.0422 (4)
H1A	1.0306	0.3855	0.0928	0.063*
H2B	1.0196	0.1165	0.0863	0.063*
H2A	0.9765	0.0299	0.1132	0.063*
H1B	0.9960	0.4708	0.1253	0.063*
N7	0.9905 (2)	0.7903 (3)	0.2248 (2)	0.0372 (9)*	0.50
N7'	0.9955 (3)	0.6972 (3)	0.2281 (2)	0.0402 (10)*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sr1	0.02894 (17)	0.02498 (17)	0.02556 (16)	0.000	0.00346 (10)	0.000
N1	0.0351 (10)	0.0383 (11)	0.0444 (11)	0.0036 (8)	0.0091 (8)	0.0031 (8)
N2	0.0303 (9)	0.0381 (11)	0.0410 (10)	−0.0018 (8)	0.0055 (8)	−0.0004 (8)
N3	0.0600 (13)	0.0401 (12)	0.0475 (12)	0.0021 (10)	0.0188 (10)	0.0097 (10)
N4	0.0579 (13)	0.0402 (12)	0.0357 (11)	−0.0054 (10)	0.0137 (9)	−0.0052 (9)
N5	0.0661 (14)	0.0409 (12)	0.0468 (13)	0.0056 (10)	0.0219 (11)	0.0081 (10)
N6	0.0777 (16)	0.0429 (13)	0.0628 (15)	−0.0153 (11)	0.0351 (12)	−0.0181 (11)
C1	0.0492 (14)	0.0412 (15)	0.0646 (17)	0.0034 (12)	0.0158 (13)	0.0056 (12)
C2	0.0677 (19)	0.0477 (16)	0.080 (2)	0.0209 (15)	0.0230 (16)	0.0199 (15)
C3	0.0494 (16)	0.076 (2)	0.0629 (18)	0.0234 (15)	0.0091 (14)	0.0244 (15)
C4	0.0358 (13)	0.0629 (17)	0.0431 (14)	0.0105 (12)	0.0079 (11)	0.0109 (12)
C5	0.0306 (13)	0.100 (3)	0.0496 (16)	0.0040 (15)	−0.0043 (11)	0.0083 (15)
C6	0.0347 (14)	0.085 (2)	0.0545 (16)	−0.0105 (14)	−0.0030 (12)	−0.0043 (15)
C7	0.0343 (12)	0.0602 (16)	0.0429 (14)	−0.0072 (11)	0.0084 (10)	−0.0061 (12)
C8	0.0468 (15)	0.0569 (17)	0.0618 (17)	−0.0206 (13)	0.0145 (13)	−0.0149 (13)
C9	0.0529 (15)	0.0402 (14)	0.0688 (17)	−0.0090 (12)	0.0190 (13)	−0.0052 (12)
C10	0.0404 (13)	0.0387 (14)	0.0560 (15)	−0.0007 (10)	0.0089 (11)	−0.0003 (11)
C11	0.0276 (11)	0.0495 (14)	0.0352 (12)	0.0036 (10)	0.0085 (9)	0.0029 (10)
C12	0.0274 (11)	0.0474 (13)	0.0321 (11)	−0.0010 (10)	0.0077 (9)	−0.0024 (10)
C13	0.0404 (13)	0.0722 (19)	0.0315 (12)	−0.0124 (12)	0.0114 (10)	−0.0074 (13)
O1	0.0655 (11)	0.0362 (9)	0.0407 (9)	0.0076 (8)	0.0203 (8)	0.0097 (7)
O2	0.0585 (10)	0.0339 (8)	0.0353 (8)	−0.0051 (7)	0.0142 (7)	−0.0054 (6)

Geometric parameters (Å, º) top

Sr1—O1ⁱ	2.5527 (15)	C4—C5	1.435 (4)
Sr1—O1	2.5527 (15)	C5—C6	1.334 (4)
Sr1—O2	2.5704 (14)	C5—H5	0.9300
Sr1—O2ⁱ	2.5704 (14)	C6—C7	1.429 (3)
Sr1—N1ⁱ	2.7985 (18)	C6—H6	0.9300
Sr1—N1	2.7985 (18)	C7—C8	1.400 (4)
Sr1—N2	2.8185 (17)	C7—C12	1.413 (3)
Sr1—N2ⁱ	2.8185 (17)	C8—C9	1.358 (4)
N1—C1	1.322 (3)	C8—H8	0.9300
N1—C11	1.358 (3)	C9—C10	1.394 (3)
N2—C10	1.321 (3)	C9—H9	0.9300
N2—C12	1.361 (3)	C10—H10	0.9300
N3—C13	1.317 (3)	C11—C12	1.442 (3)
N3—N4	1.327 (3)	C13—N7	1.434 (4)
N4—N5	1.310 (3)	C13—N7'	1.496 (4)
N5—N6	1.327 (3)	O1—H1A	0.8503
N6—C13	1.314 (3)	O1—H1B	0.8520
C1—C2	1.396 (3)	O2—H2B	0.8499
C1—H1	0.9300	O2—H2A	0.8500
C2—C3	1.363 (4)	N7—N7ⁱ	0.797 (6)
C2—H2	0.9300	N7—N7'	1.018 (5)
C3—C4	1.395 (4)	N7—N7'ⁱ	1.254 (5)
C3—H3	0.9300	N7'—N7'ⁱ	0.686 (6)
C4—C11	1.410 (3)	N7'—N7ⁱ	1.254 (5)

O1ⁱ—Sr1—O1	96.53 (7)	C11—C4—C5	119.4 (2)
O1ⁱ—Sr1—O2	168.21 (5)	C6—C5—C4	121.5 (2)
O1—Sr1—O2	78.63 (5)	C6—C5—H5	119.3
O1ⁱ—Sr1—O2ⁱ	78.63 (5)	C4—C5—H5	119.3
O1—Sr1—O2ⁱ	168.21 (5)	C5—C6—C7	121.3 (2)
O2—Sr1—O2ⁱ	108.08 (7)	C5—C6—H6	119.4
O1ⁱ—Sr1—N1ⁱ	73.85 (5)	C7—C6—H6	119.4
O1—Sr1—N1ⁱ	74.48 (5)	C8—C7—C12	117.8 (2)
O2—Sr1—N1ⁱ	114.54 (5)	C8—C7—C6	123.0 (2)
O2ⁱ—Sr1—N1ⁱ	93.80 (5)	C12—C7—C6	119.2 (2)
O1ⁱ—Sr1—N1	74.48 (5)	C9—C8—C7	119.9 (2)
O1—Sr1—N1	73.85 (5)	C9—C8—H8	120.0
O2—Sr1—N1	93.80 (5)	C7—C8—H8	120.0
O2ⁱ—Sr1—N1	114.54 (5)	C8—C9—C10	118.2 (2)
N1ⁱ—Sr1—N1	131.59 (8)	C8—C9—H9	120.9
O1ⁱ—Sr1—N2	103.91 (5)	C10—C9—H9	120.9
O1—Sr1—N2	118.66 (5)	N2—C10—C9	124.7 (2)
O2—Sr1—N2	69.86 (5)	N2—C10—H10	117.7
O2ⁱ—Sr1—N2	73.09 (5)	C9—C10—H10	117.7
N1ⁱ—Sr1—N2	166.84 (5)	N1—C11—C4	123.1 (2)
N1—Sr1—N2	57.97 (5)	N1—C11—C12	118.00 (18)
O1ⁱ—Sr1—N2ⁱ	118.66 (5)	C4—C11—C12	118.9 (2)
O1—Sr1—N2ⁱ	103.91 (5)	N2—C12—C7	122.1 (2)
O2—Sr1—N2ⁱ	73.09 (5)	N2—C12—C11	118.15 (19)
O2ⁱ—Sr1—N2ⁱ	69.86 (5)	C7—C12—C11	119.7 (2)
N1ⁱ—Sr1—N2ⁱ	57.97 (5)	N6—C13—N3	112.7 (2)
N1—Sr1—N2ⁱ	166.84 (5)	N6—C13—N7	102.6 (2)
N2—Sr1—N2ⁱ	114.53 (7)	N3—C13—N7	144.7 (3)
C1—N1—C11	117.0 (2)	N6—C13—N7'	143.2 (3)
C1—N1—Sr1	120.81 (16)	N3—C13—N7'	104.1 (2)
C11—N1—Sr1	120.12 (14)	N7—C13—N7'	40.60 (19)
C10—N2—C12	117.23 (19)	Sr1—O1—H1A	127.1
C10—N2—Sr1	120.88 (14)	Sr1—O1—H1B	131.5
C12—N2—Sr1	119.09 (14)	H1A—O1—H1B	98.8
C13—N3—N4	104.26 (19)	Sr1—O2—H2B	120.3
N5—N4—N3	109.29 (18)	Sr1—O2—H2A	128.2
N4—N5—N6	109.49 (18)	H2B—O2—H2A	104.9
C13—N6—N5	104.26 (19)	N7ⁱ—N7—N7'	86.5 (3)
N1—C1—C2	124.0 (2)	N7ⁱ—N7—N7'ⁱ	54.1 (2)
N1—C1—H1	118.0	N7'—N7—N7'ⁱ	33.1 (3)
C2—C1—H1	118.0	N7ⁱ—N7—C13	157.9 (4)
C3—C2—C1	118.8 (3)	N7'—N7—C13	73.0 (3)
C3—C2—H2	120.6	N7'ⁱ—N7—C13	106.1 (3)
C1—C2—H2	120.6	N7'ⁱ—N7'—N7	92.7 (3)
C2—C3—C4	119.8 (2)	N7'ⁱ—N7'—N7ⁱ	54.2 (2)
C2—C3—H3	120.1	N7—N7'—N7ⁱ	39.4 (3)
C4—C3—H3	120.1	N7'ⁱ—N7'—C13	159.0 (2)
C3—C4—C11	117.2 (2)	N7—N7'—C13	66.4 (3)
C3—C4—C5	123.4 (2)	N7ⁱ—N7'—C13	105.4 (3)

O1ⁱ—Sr1—N1—C1	58.23 (18)	C1—N1—C11—C4	2.7 (3)
O1—Sr1—N1—C1	−43.51 (18)	Sr1—N1—C11—C4	−160.92 (17)
O2—Sr1—N1—C1	−120.51 (18)	C1—N1—C11—C12	−176.1 (2)
O2ⁱ—Sr1—N1—C1	127.64 (18)	Sr1—N1—C11—C12	20.3 (3)
N1ⁱ—Sr1—N1—C1	7.47 (17)	C3—C4—C11—N1	−1.4 (4)
N2—Sr1—N1—C1	176.1 (2)	C5—C4—C11—N1	178.8 (2)
N2ⁱ—Sr1—N1—C1	−125.5 (3)	C3—C4—C11—C12	177.3 (2)
O1ⁱ—Sr1—N1—C11	−138.79 (17)	C5—C4—C11—C12	−2.4 (3)
O1—Sr1—N1—C11	119.47 (17)	C10—N2—C12—C7	−1.1 (3)
O2—Sr1—N1—C11	42.47 (16)	Sr1—N2—C12—C7	160.13 (16)
O2ⁱ—Sr1—N1—C11	−69.38 (17)	C10—N2—C12—C11	177.5 (2)
N1ⁱ—Sr1—N1—C11	170.45 (17)	Sr1—N2—C12—C11	−21.3 (2)
N2—Sr1—N1—C11	−20.89 (15)	C8—C7—C12—N2	0.0 (3)
N2ⁱ—Sr1—N1—C11	37.5 (3)	C6—C7—C12—N2	−180.0 (2)
O1ⁱ—Sr1—N2—C10	−117.05 (17)	C8—C7—C12—C11	−178.5 (2)
O1—Sr1—N2—C10	137.34 (17)	C6—C7—C12—C11	1.5 (3)
O2—Sr1—N2—C10	73.43 (17)	N1—C11—C12—N2	0.9 (3)
O2ⁱ—Sr1—N2—C10	−43.77 (17)	C4—C11—C12—N2	−177.9 (2)
N1ⁱ—Sr1—N2—C10	−38.6 (3)	N1—C11—C12—C7	179.5 (2)
N1—Sr1—N2—C10	−178.36 (19)	C4—C11—C12—C7	0.7 (3)
N2ⁱ—Sr1—N2—C10	13.94 (16)	N5—N6—C13—N3	0.6 (3)
O1ⁱ—Sr1—N2—C12	82.42 (15)	N5—N6—C13—N7	−179.0 (2)
O1—Sr1—N2—C12	−23.18 (17)	N5—N6—C13—N7'	178.2 (4)
O2—Sr1—N2—C12	−87.10 (15)	N4—N3—C13—N6	−0.5 (3)
O2ⁱ—Sr1—N2—C12	155.71 (16)	N4—N3—C13—N7	178.8 (4)
N1ⁱ—Sr1—N2—C12	160.9 (2)	N4—N3—C13—N7'	−179.1 (2)
N1—Sr1—N2—C12	21.11 (14)	N6—C13—N7—N7ⁱ	−154.7 (17)
N2ⁱ—Sr1—N2—C12	−146.58 (16)	N3—C13—N7—N7ⁱ	26 (2)
C13—N3—N4—N5	0.3 (3)	N7'—C13—N7—N7ⁱ	22.7 (16)
N3—N4—N5—N6	0.1 (2)	N6—C13—N7—N7'	−177.5 (4)
N4—N5—N6—C13	−0.4 (3)	N3—C13—N7—N7'	3.2 (6)
C11—N1—C1—C2	−2.2 (4)	N6—C13—N7—N7'ⁱ	−178.9 (3)
Sr1—N1—C1—C2	161.3 (2)	N3—C13—N7—N7'ⁱ	1.7 (6)
N1—C1—C2—C3	0.5 (4)	N7'—C13—N7—N7'ⁱ	−1.4 (5)
C1—C2—C3—C4	0.8 (4)	N7ⁱ—N7—N7'—N7'ⁱ	10.9 (10)
C2—C3—C4—C11	−0.4 (4)	C13—N7—N7'—N7'ⁱ	−177.5 (8)
C2—C3—C4—C5	179.3 (3)	N7'ⁱ—N7—N7'—N7ⁱ	−10.9 (10)
C3—C4—C5—C6	−177.7 (3)	C13—N7—N7'—N7ⁱ	171.6 (7)
C11—C4—C5—C6	2.0 (4)	N7ⁱ—N7—N7'—C13	−171.6 (7)
C4—C5—C6—C7	0.2 (5)	N7'ⁱ—N7—N7'—C13	177.5 (8)
C5—C6—C7—C8	178.0 (3)	N6—C13—N7'—N7'ⁱ	11 (3)
C5—C6—C7—C12	−1.9 (4)	N3—C13—N7'—N7'ⁱ	−171 (2)
C12—C7—C8—C9	1.1 (4)	N7—C13—N7'—N7'ⁱ	7 (2)
C6—C7—C8—C9	−178.9 (3)	N6—C13—N7'—N7	4.1 (6)
C7—C8—C9—C10	−1.2 (4)	N3—C13—N7'—N7	−178.1 (4)
C12—N2—C10—C9	1.1 (4)	N6—C13—N7'—N7ⁱ	−1.3 (6)
Sr1—N2—C10—C9	−159.8 (2)	N3—C13—N7'—N7ⁱ	176.4 (3)
C8—C9—C10—N2	0.0 (4)	N7—C13—N7'—N7ⁱ	−5.5 (4)

Symmetry code: (i) −x+2, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2B···N5ⁱⁱ	0.85	2.08	2.885 (3)	158
O1—H1A···N4ⁱⁱ	0.85	2.04	2.870 (2)	167
O2—H2A···N6ⁱⁱⁱ	0.85	2.03	2.871 (3)	173
O1—H1B···N3	0.85	2.04	2.887 (3)	172

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

Experimental details

Crystal data
Chemical formula	[Sr(C₁₂H₈N₂)₂(H₂O)₄](C₂N₁₀)
M_r	684.21
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	17.442 (3), 10.8974 (17), 16.189 (3)
β (°)	105.178 (2)
V (Å³)	2969.8 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.88
Crystal size (mm)	0.25 × 0.20 × 0.18

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Empirical (using intensity measurements) (SADABS; Bruker, 2002)
T_min, T_max	0.652, 0.729
No. of measured, independent and observed [I > 2σ(I)] reflections	7165, 2621, 2226
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.069, 1.04
No. of reflections	2621
No. of parameters	204
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.37

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), 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
O2—H2B···N5ⁱ	0.85	2.08	2.885 (3)	158.3
O1—H1A···N4ⁱ	0.85	2.04	2.870 (2)	166.8
O2—H2A···N6ⁱⁱ	0.85	2.03	2.871 (3)	172.5
O1—H1B···N3	0.85	2.04	2.887 (3)	172.4

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

Acknowledgements

This work was supported by the National Science Foundation of China (grant No. 21003103) and the Research Foundation of Xi'an University of Arts and Science (grant Nos. kyc201026 and kyc201011). The authors thank the Instrumental Analysis Center of Northwest University for data collection on the CCD facility.

References

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