Crystal structure of [NaZn(BTC)(H2O)4]·1.5H2O (BTC = benzene-1,3,5-tri­carb­oxy­l­ate): a heterometallic coordination compound

Ni, M.; Li, Q.; Chen, H.; Li, S.

doi:10.1107/S2056989015012001

metal-organic compounds

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ISSN: 2056-9890

Volume 71| Part 7| July 2015| Pages m143-m144

doi:10.1107/S2056989015012001

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Crystal structure of [NaZn(BTC)(H₂O)₄]·1.5H₂O (BTC = benzene-1,3,5-tricarboxylate): a heterometallic coordination compound

Min Ni,^a Quanle Li,^a Hao Chen ^a and Shengqing Li ^a ^*

^aCollege of Science, Huazhong Agricultural University, Wuhan, Hubei 430070, People's Republic of China
^*Correspondence e-mail: sqingli@mail.hzau.edu.cn

Edited by P. Bombicz, Hungarian Academy of Sciences, Hungary (Received 28 March 2015; accepted 23 June 2015; online 27 June 2015)

The title coordination polymer, poly[[μ-aqua-triaqua(μ₃-benzene-1,3,5-tricarboxylato)sodiumzinc] sesquihydrate], {[NaZn(C₉H₃O₆)(H₂O)₄]·1.5H₂O}_n, was obtained in ionic liquid microemulsion at room temperture by the reaction of benzene-1,3,5-tricarboxylic acid (H₃BTC) with Zn(NO₃)₂·6H₂O in the presence of NaOH. The asymmetric unit comprises two Na⁺ ions (each located on an inversion centre), one Zn²⁺ ion, one BTC ligand, four coordinating water molecules and two solvent water molecules, one of which is disordered about an inversion centre and shows half-occupation. The Zn²⁺ cation is five-coordinated by two carboxylate O atoms from two different BTC ligands and three coordinating H₂O molecules; the Zn—O bond lengths are in the range 1.975 (2)–2.058 (3) Å. The Na⁺ cations are six-coordinated but have different arrangements of the ligands: one is bound to two carboxylate O atoms of two BTC ligands and four O atoms from four coordinating H₂O molecules while the other is bound by four carboxylate O atoms from four BTC linkers and two O atoms of coordinating H₂O molecules. The completely deprotonated BTC ligand acts as a bridging ligand binding the Zn²⁺ atom and Na⁺ ions, forming a layered structure extending parallel to (100). An intricate network of O—H⋯O hydrogen bonds is present within and between the layers.

Keywords: crystal structure; heterometallic coordination compound; benzene-1,3,5-tricarboxylic acid; hydrogen bonding.

CCDC reference: 1055450

1. Related literature

For general background to heterometallic coordination compounds, see: Stock & Biswas (2012 ); Gao et al. (2005 ); Zhou et al. (2012 ). For details of the synthesis, see: Shang et al. (2013 ); Fu et al. (2011 ). For the potential application of this compound, see: Huang et al. (2014 ).

2. Experimental

2.1. Crystal data

[NaZn(C₉H₃O₆)(H₂O)₄]·1.5H₂O
M_r = 394.56
Triclinic, $[P \overline 1]$
a = 7.0980 (11) Å
b = 9.8000 (16) Å
c = 11.2043 (17) Å
α = 66.923 (2)°
β = 73.598 (2)°
γ = 84.720 (3)°
V = 687.68 (19) Å³
Z = 2
Mo Kα radiation
μ = 1.88 mm⁻¹
T = 296 K
0.05 × 0.03 × 0.02 mm

2.2. Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.912, T_max = 0.963
7585 measured reflections
4331 independent reflections
2567 reflections with I > 2σ(I)
R_int = 0.051

2.3. Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.113
S = 0.97
4331 reflections
214 parameters
H-atom parameters constrained
Δρ_max = 0.79 e Å⁻³
Δρ_min = −0.69 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H7A⋯O5ⁱ	0.82	1.79	2.587 (4)	162
O7—H7B⋯O12ⁱⁱ	0.82	1.93	2.740 (4)	172
O8—H8A⋯O10	0.82	2.40	3.114 (5)	146
O8—H8A⋯O11	0.82	1.98	2.672 (8)	142
O8—H8B⋯O6ⁱⁱ	0.82	2.05	2.641 (5)	128
O9—H9A⋯O12ⁱⁱⁱ	0.82	1.95	2.734 (4)	159
O9—H9B⋯O2^iv	0.82	2.01	2.823 (4)	170
O10—H10A⋯O5^v	0.82	2.06	2.719 (6)	137
O10—H10B⋯O9^vi	0.82	2.31	3.079 (5)	155
O11—H11A⋯O3^vii	0.85	2.03	2.835 (8)	157
O11—H11B⋯O3^v	0.85	2.27	2.866 (7)	127
O11—H11B⋯O11^viii	0.85	1.33	1.973 (9)	128
O12—H12A⋯O6	0.82	1.86	2.652 (4)	161
O12—H12B⋯O4^ix	0.82	1.97	2.787 (3)	172
Symmetry codes: (i) x, y+1, z-1; (ii) -x+1, -y+2, -z+1; (iii) -x+2, -y+2, -z+1; (iv) -x+2, -y+2, -z; (v) -x+1, -y+1, -z+1; (vi) x-1, y, z; (vii) x-1, y+1, z; (viii) -x, -y+2, -z+1; (ix) x, y, z+1.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS7 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015 ); molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: OLEX2.

Supporting information

CCDC reference: 1055450

Crystal structure: contains datablock I. DOI: 10.1107/S2056989015012001/zp2017sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015012001/zp2017Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015012001/zp2017Isup3.docx

checkCIF report

Synthesis and crystallization top

In the experiment, the microemulsion of desired composition containing water, [Bmim]PF₆, and Triton X-100 was prepared using the method reported previously (Gao et al. 2005). H₃BTC (0.210 g, 1.0 mmol), NaOH (0.040 g, 1.0 mmol) and Zn(NO₃)₂.6H₂O (0.298 g, 1.0 mmol) were added one by one into the microemulsion (20 g) which was clear and transparent system including 1.444 g [Bmim]PF₆, 10.428 g Triton X-100 and 8.310 g water. The whole system was stirred continuously for 24 h at 25^oC. Then, the product crystals were collected by centrifugation at 4500 r/min and washed with alcohol three times (3x20 mL) to remove the surfactant and [Bmim]PF₆. Then, the crystals were dried in a vacuum oven at 60^oC for 24 h. The resulting colorless crystals of the title compound were obtained.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1.

Related literature top

For general background [to what?], see: Stock & Biswas (2012); Gao et al. (2005); Zhou et al. (2012). For details of the synthesis, see: Shang et al. (2013); Fu et al. (2011). For the potential application of this compound, see: Huang et al. (2014).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus (Bruker, 2009); program(s) used to solve structure: SHELXS7 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom-numbering scheme and 30% probability ellipsoids.
	Fig. 2. The packing diagram viewed along the b axis.
	Fig. 3. The FT–IR spectrum of the title compound.
	Fig. 4. The XRD pattern of the title compound.

Poly[[µ-aqua-triaqua(µ₃-benzene-1,3,5-tricarboxylato)sodiumzinc] sesquihydrate] top

Crystal data top

[NaZn(C₉H₃O₆)(H₂O)₄]·1.5H₂O	Z = 2
M_r = 394.56	F(000) = 402
Triclinic, P1	D_x = 1.906 Mg m⁻³
a = 7.0980 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.8000 (16) Å	Cell parameters from 1047 reflections
c = 11.2043 (17) Å	θ = 2.4–22.5°
α = 66.923 (2)°	µ = 1.88 mm⁻¹
β = 73.598 (2)°	T = 296 K
γ = 84.720 (3)°	Block, colourless
V = 687.68 (19) Å³	0.05 × 0.03 × 0.02 mm

Data collection top

Bruker APEXII CCD diffractometer	2567 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.051
ϕ and ω scans	θ_max = 32.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
T_min = 0.912, T_max = 0.963	k = −14→14
7585 measured reflections	l = −16→16
4331 independent reflections

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)] = 0.051	Hydrogen site location: mixed
wR(F²) = 0.113	H-atom parameters constrained
S = 0.97	w = 1/[σ²(F_o²) + (0.0356P)²] where P = (F_o² + 2F_c²)/3
4331 reflections	(Δ/σ)_max = 0.001
214 parameters	Δρ_max = 0.79 e Å⁻³
0 restraints	Δρ_min = −0.69 e Å⁻³

Crystal data top

[NaZn(C₉H₃O₆)(H₂O)₄]·1.5H₂O	γ = 84.720 (3)°
M_r = 394.56	V = 687.68 (19) Å³
Triclinic, P1	Z = 2
a = 7.0980 (11) Å	Mo Kα radiation
b = 9.8000 (16) Å	µ = 1.88 mm⁻¹
c = 11.2043 (17) Å	T = 296 K
α = 66.923 (2)°	0.05 × 0.03 × 0.02 mm
β = 73.598 (2)°

Data collection top

Bruker APEXII CCD diffractometer	4331 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2567 reflections with I > 2σ(I)
T_min = 0.912, T_max = 0.963	R_int = 0.051
7585 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.113	H-atom parameters constrained
S = 0.97	Δρ_max = 0.79 e Å⁻³
4331 reflections	Δρ_min = −0.69 e Å⁻³
214 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. olex2_refinement_description 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All O(H,H) groups 2. Others Fixed Sof: O11(0.5) H11A(0.5) H11B(0.5) 3.a Riding coordinates: O7(H7A,H7B), O8(H8A,H8B), O9(H9A,H9B), O10(H10A,H10B), O12(H12A,H12B) 3.b Free rotating group: O11(H11A,H11B) 3.c Aromatic/amide H refined with riding coordinates: C2(H2), C4(H4), C6(H6)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Zn1	0.69252 (6)	1.17043 (4)	0.17723 (4)	0.02302 (13)
Na1	0.5000	1.0000	0.0000	0.0322 (5)
Na2	0.5000	0.0000	0.5000	0.0319 (5)
C1	0.7424 (5)	0.7068 (3)	0.3327 (3)	0.0184 (7)
C2	0.7376 (5)	0.5950 (3)	0.2865 (3)	0.0186 (7)
H2	0.7312	0.6192	0.1988	0.022*
C3	0.7423 (5)	0.4476 (3)	0.3710 (3)	0.0188 (7)
C4	0.7512 (5)	0.4130 (4)	0.5013 (3)	0.0207 (7)
H4	0.7529	0.3140	0.5581	0.025*
C5	0.7576 (5)	0.5231 (4)	0.5492 (3)	0.0211 (7)
C6	0.7566 (5)	0.6703 (4)	0.4623 (3)	0.0204 (7)
H6	0.7657	0.7455	0.4917	0.024*
C7	0.7273 (5)	0.8667 (4)	0.2423 (3)	0.0204 (7)
C8	0.7345 (5)	0.3229 (4)	0.3272 (3)	0.0206 (7)
C9	0.7632 (5)	0.4837 (5)	0.6923 (4)	0.0291 (8)
O1	0.7044 (4)	0.9607 (3)	0.2967 (3)	0.0371 (7)
O2	0.7376 (4)	0.8999 (3)	0.1217 (3)	0.0341 (6)
O3	0.7335 (4)	0.1931 (3)	0.4071 (3)	0.0325 (6)
O4	0.7242 (4)	0.3558 (3)	0.2063 (2)	0.0268 (6)
O5	0.7596 (4)	0.3477 (4)	0.7661 (3)	0.0467 (8)
O6	0.7682 (4)	0.5863 (4)	0.7316 (3)	0.0479 (8)
O7	0.5762 (4)	1.2363 (3)	0.0195 (2)	0.0292 (6)
H7A	0.6483	1.2811	−0.0557	0.044*
H7B	0.4703	1.2778	0.0249	0.044*
O8	0.3875 (4)	1.1497 (3)	0.3061 (3)	0.0396 (7)
H8A	0.3040	1.0995	0.3031	0.059*
H8B	0.3305	1.2022	0.3464	0.059*
O9	0.9800 (4)	1.1943 (3)	0.0630 (3)	0.0382 (7)
H9A	1.0364	1.2580	0.0713	0.057*
H9B	1.0536	1.1721	0.0026	0.057*
O10	0.2322 (5)	0.9423 (4)	0.2021 (4)	0.0790 (13)
H10A	0.1808	0.8593	0.2402	0.119*
H10B	0.1445	1.0027	0.1899	0.119*
O11	0.0497 (9)	0.9938 (8)	0.4107 (6)	0.0482 (16)	0.5
H11A	−0.0558	1.0390	0.3993	0.072*	0.5
H11B	0.0429	0.9553	0.4942	0.072*	0.5
O12	0.7580 (4)	0.6003 (3)	0.9650 (2)	0.0294 (6)
H12A	0.7717	0.5773	0.9002	0.044*
H12B	0.7499	0.5234	1.0318	0.044*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0340 (2)	0.01306 (19)	0.0218 (2)	−0.00099 (15)	−0.00540 (16)	−0.00759 (16)
Na1	0.0424 (13)	0.0290 (11)	0.0309 (12)	0.0027 (9)	−0.0169 (10)	−0.0128 (10)
Na2	0.0457 (13)	0.0204 (10)	0.0228 (11)	−0.0072 (9)	−0.0013 (9)	−0.0048 (9)
C1	0.0191 (16)	0.0153 (15)	0.0210 (17)	−0.0019 (12)	−0.0009 (13)	−0.0096 (13)
C2	0.0267 (18)	0.0163 (16)	0.0141 (16)	−0.0003 (13)	−0.0044 (13)	−0.0078 (13)
C3	0.0211 (17)	0.0145 (15)	0.0205 (17)	−0.0018 (12)	−0.0023 (13)	−0.0081 (13)
C4	0.0239 (18)	0.0150 (16)	0.0184 (17)	0.0016 (13)	−0.0045 (13)	−0.0025 (13)
C5	0.0217 (17)	0.0228 (17)	0.0150 (17)	0.0005 (13)	−0.0033 (13)	−0.0045 (14)
C6	0.0259 (18)	0.0190 (16)	0.0194 (17)	0.0014 (13)	−0.0039 (13)	−0.0123 (14)
C7	0.0221 (17)	0.0146 (16)	0.0221 (18)	−0.0014 (13)	−0.0017 (14)	−0.0070 (14)
C8	0.0229 (17)	0.0170 (16)	0.0221 (18)	0.0007 (13)	−0.0047 (14)	−0.0089 (14)
C9	0.0241 (19)	0.044 (2)	0.0187 (19)	0.0110 (16)	−0.0063 (15)	−0.0131 (18)
O1	0.071 (2)	0.0100 (12)	0.0212 (14)	0.0004 (12)	0.0018 (13)	−0.0062 (11)
O2	0.0607 (19)	0.0187 (13)	0.0253 (15)	0.0030 (12)	−0.0202 (13)	−0.0053 (11)
O3	0.0481 (17)	0.0124 (12)	0.0351 (16)	0.0001 (11)	−0.0128 (12)	−0.0058 (11)
O4	0.0411 (15)	0.0191 (12)	0.0235 (14)	−0.0019 (10)	−0.0079 (11)	−0.0117 (11)
O5	0.0529 (19)	0.053 (2)	0.0203 (15)	0.0040 (15)	−0.0114 (13)	0.0006 (14)
O6	0.058 (2)	0.070 (2)	0.0325 (17)	0.0229 (17)	−0.0228 (14)	−0.0346 (17)
O7	0.0337 (15)	0.0261 (14)	0.0213 (14)	0.0047 (11)	−0.0037 (11)	−0.0057 (11)
O8	0.0298 (15)	0.065 (2)	0.0303 (16)	−0.0049 (13)	−0.0034 (12)	−0.0265 (15)
O9	0.0386 (17)	0.0369 (16)	0.0418 (18)	−0.0062 (12)	0.0029 (13)	−0.0260 (14)
O10	0.059 (2)	0.062 (3)	0.068 (3)	0.0028 (18)	−0.0052 (18)	0.016 (2)
O11	0.041 (4)	0.052 (4)	0.052 (4)	0.008 (3)	−0.018 (3)	−0.019 (4)
O12	0.0440 (16)	0.0224 (13)	0.0223 (14)	−0.0001 (11)	−0.0096 (11)	−0.0086 (11)

Geometric parameters (Å, º) top

Zn1—Na1	3.6267 (5)	C3—C8	1.495 (4)
Zn1—Na2ⁱ	3.2603 (6)	C4—H4	0.9300
Zn1—O1	1.975 (2)	C4—C5	1.390 (5)
Zn1—O4ⁱ	2.009 (2)	C5—C6	1.390 (4)
Zn1—O7	2.013 (2)	C5—C9	1.506 (5)
Zn1—O8	2.214 (3)	C6—H6	0.9300
Zn1—O9	2.058 (3)	C7—O1	1.267 (4)
Na1—Zn1ⁱⁱ	3.6267 (5)	C7—O2	1.242 (4)
Na1—O2	2.369 (3)	C8—O3	1.235 (4)
Na1—O2ⁱⁱ	2.369 (3)	C8—O4	1.286 (4)
Na1—O7	2.529 (3)	C9—O5	1.262 (5)
Na1—O7ⁱⁱ	2.529 (3)	C9—O6	1.252 (5)
Na1—O10	2.413 (3)	O1—Na2ⁱ	2.482 (2)
Na1—O10ⁱⁱ	2.413 (3)	O4—Zn1^iv	2.009 (2)
Na2—Zn1ⁱⁱⁱ	3.2603 (6)	O7—H7A	0.8201
Na2—Zn1^iv	3.2603 (6)	O7—H7B	0.8201
Na2—O1^iv	2.482 (2)	O8—Na2ⁱ	2.403 (3)
Na2—O1ⁱⁱⁱ	2.482 (2)	O8—H8A	0.8200
Na2—O3	2.339 (3)	O8—H8B	0.8201
Na2—O3^v	2.339 (3)	O9—H9A	0.8199
Na2—O8ⁱⁱⁱ	2.403 (3)	O9—H9B	0.8200
Na2—O8^iv	2.403 (3)	O10—H10A	0.8200
C1—C2	1.389 (4)	O10—H10B	0.8200
C1—C6	1.384 (4)	O11—H11A	0.8500
C1—C7	1.509 (4)	O11—H11B	0.8500
C2—H2	0.9300	O12—H12A	0.8203
C2—C3	1.386 (4)	O12—H12B	0.8200
C3—C4	1.382 (4)

Na2ⁱ—Zn1—Na1	108.751 (15)	O3^v—Na2—O8ⁱⁱⁱ	81.75 (9)
O1—Zn1—Na1	81.47 (8)	O3—Na2—O8ⁱⁱⁱ	98.25 (9)
O1—Zn1—Na2ⁱ	49.45 (7)	O3—Na2—O8^iv	81.75 (9)
O1—Zn1—O4ⁱ	129.50 (11)	O8ⁱⁱⁱ—Na2—Zn1^iv	137.24 (6)
O1—Zn1—O7	123.49 (11)	O8^iv—Na2—Zn1ⁱⁱⁱ	137.24 (6)
O1—Zn1—O8	83.14 (11)	O8ⁱⁱⁱ—Na2—Zn1ⁱⁱⁱ	42.76 (6)
O1—Zn1—O9	97.22 (11)	O8^iv—Na2—Zn1^iv	42.76 (6)
O4ⁱ—Zn1—Na1	147.26 (7)	O8ⁱⁱⁱ—Na2—O1ⁱⁱⁱ	69.50 (9)
O4ⁱ—Zn1—Na2ⁱ	89.66 (7)	O8ⁱⁱⁱ—Na2—O1^iv	110.50 (9)
O4ⁱ—Zn1—O7	105.44 (10)	O8^iv—Na2—O1^iv	69.50 (9)
O4ⁱ—Zn1—O8	88.15 (11)	O8^iv—Na2—O1ⁱⁱⁱ	110.50 (9)
O4ⁱ—Zn1—O9	89.49 (10)	O8ⁱⁱⁱ—Na2—O8^iv	180.0
O7—Zn1—Na1	42.24 (7)	C2—C1—C7	119.8 (3)
O7—Zn1—Na2ⁱ	131.91 (7)	C6—C1—C2	119.7 (3)
O7—Zn1—O8	86.91 (10)	C6—C1—C7	120.6 (3)
O7—Zn1—O9	95.17 (11)	C1—C2—H2	119.9
O8—Zn1—Na1	85.30 (7)	C3—C2—C1	120.1 (3)
O8—Zn1—Na2ⁱ	47.48 (7)	C3—C2—H2	119.9
O9—Zn1—Na1	97.50 (8)	C2—C3—C8	122.3 (3)
O9—Zn1—Na2ⁱ	131.02 (8)	C4—C3—C2	119.4 (3)
O9—Zn1—O8	177.20 (11)	C4—C3—C8	118.2 (3)
Zn1—Na1—Zn1ⁱⁱ	180.0	C3—C4—H4	119.3
O2—Na1—Zn1	53.49 (6)	C3—C4—C5	121.4 (3)
O2ⁱⁱ—Na1—Zn1ⁱⁱ	53.49 (6)	C5—C4—H4	119.3
O2ⁱⁱ—Na1—Zn1	126.51 (6)	C4—C5—C9	120.8 (3)
O2—Na1—Zn1ⁱⁱ	126.51 (6)	C6—C5—C4	118.3 (3)
O2ⁱⁱ—Na1—O2	180.0	C6—C5—C9	120.8 (3)
O2ⁱⁱ—Na1—O7ⁱⁱ	83.14 (8)	C1—C6—C5	121.0 (3)
O2—Na1—O7	83.14 (8)	C1—C6—H6	119.5
O2ⁱⁱ—Na1—O7	96.86 (8)	C5—C6—H6	119.5
O2—Na1—O7ⁱⁱ	96.86 (8)	O1—C7—C1	116.3 (3)
O2—Na1—O10ⁱⁱ	86.91 (11)	O2—C7—C1	120.1 (3)
O2ⁱⁱ—Na1—O10ⁱⁱ	93.09 (11)	O2—C7—O1	123.6 (3)
O2ⁱⁱ—Na1—O10	86.91 (11)	O3—C8—C3	120.1 (3)
O2—Na1—O10	93.09 (11)	O3—C8—O4	122.0 (3)
O7ⁱⁱ—Na1—Zn1	147.65 (5)	O4—C8—C3	117.9 (3)
O7—Na1—Zn1	32.36 (5)	O5—C9—C5	117.2 (4)
O7ⁱⁱ—Na1—Zn1ⁱⁱ	32.35 (5)	O6—C9—C5	118.8 (4)
O7—Na1—Zn1ⁱⁱ	147.64 (5)	O6—C9—O5	124.0 (4)
O7ⁱⁱ—Na1—O7	180.0	Zn1—O1—Na2ⁱ	93.35 (9)
O10ⁱⁱ—Na1—Zn1	99.48 (11)	C7—O1—Zn1	116.3 (2)
O10—Na1—Zn1ⁱⁱ	99.48 (11)	C7—O1—Na2ⁱ	140.1 (2)
O10—Na1—Zn1	80.52 (11)	C7—O2—Na1	130.6 (2)
O10ⁱⁱ—Na1—Zn1ⁱⁱ	80.52 (11)	C8—O3—Na2	132.2 (2)
O10—Na1—O7ⁱⁱ	89.62 (12)	C8—O4—Zn1^iv	110.2 (2)
O10—Na1—O7	90.38 (12)	Zn1—O7—Na1	105.40 (10)
O10ⁱⁱ—Na1—O7ⁱⁱ	90.38 (12)	Zn1—O7—H7A	117.9
O10ⁱⁱ—Na1—O7	89.62 (12)	Zn1—O7—H7B	118.8
O10ⁱⁱ—Na1—O10	180.0	Na1—O7—H7A	101.6
Zn1ⁱⁱⁱ—Na2—Zn1^iv	180.0	Na1—O7—H7B	102.9
O1ⁱⁱⁱ—Na2—Zn1^iv	142.80 (5)	H7A—O7—H7B	107.7
O1^iv—Na2—Zn1^iv	37.20 (5)	Zn1—O8—Na2ⁱ	89.76 (9)
O1^iv—Na2—Zn1ⁱⁱⁱ	142.80 (5)	Zn1—O8—H8A	121.4
O1ⁱⁱⁱ—Na2—Zn1ⁱⁱⁱ	37.20 (5)	Zn1—O8—H8B	129.0
O1^iv—Na2—O1ⁱⁱⁱ	180.0	Na2ⁱ—O8—H8A	106.3
O3^v—Na2—Zn1^iv	123.65 (7)	Na2ⁱ—O8—H8B	89.2
O3—Na2—Zn1^iv	56.35 (7)	H8A—O8—H8B	107.7
O3^v—Na2—Zn1ⁱⁱⁱ	56.35 (7)	Zn1—O9—H9A	109.9
O3—Na2—Zn1ⁱⁱⁱ	123.65 (7)	Zn1—O9—H9B	141.4
O3—Na2—O1ⁱⁱⁱ	102.11 (9)	H9A—O9—H9B	107.7
O3—Na2—O1^iv	77.89 (9)	Na1—O10—H10A	120.4
O3^v—Na2—O1ⁱⁱⁱ	77.89 (9)	Na1—O10—H10B	110.7
O3^v—Na2—O1^iv	102.11 (9)	H10A—O10—H10B	107.7
O3—Na2—O3^v	180.0	H11A—O11—H11B	109.5
O3^v—Na2—O8^iv	98.25 (9)	H12A—O12—H12B	107.7

C1—C2—C3—C4	0.2 (5)	C4—C5—C6—C1	2.3 (5)
C1—C2—C3—C8	179.1 (3)	C4—C5—C9—O5	−0.8 (5)
C1—C7—O1—Zn1	178.2 (2)	C4—C5—C9—O6	−179.8 (3)
C1—C7—O1—Na2ⁱ	−48.0 (5)	C6—C1—C2—C3	1.5 (5)
C1—C7—O2—Na1	114.6 (3)	C6—C1—C7—O1	−8.3 (5)
C2—C1—C6—C5	−2.8 (5)	C6—C1—C7—O2	171.6 (3)
C2—C1—C7—O1	170.3 (3)	C6—C5—C9—O5	178.5 (3)
C2—C1—C7—O2	−9.9 (5)	C6—C5—C9—O6	−0.4 (5)
C2—C3—C4—C5	−0.7 (5)	C7—C1—C2—C3	−177.0 (3)
C2—C3—C8—O3	−178.0 (3)	C7—C1—C6—C5	175.7 (3)
C2—C3—C8—O4	0.4 (5)	C8—C3—C4—C5	−179.6 (3)
C3—C4—C5—C6	−0.6 (5)	C9—C5—C6—C1	−177.1 (3)
C3—C4—C5—C9	178.8 (3)	O1—C7—O2—Na1	−65.6 (4)
C3—C8—O3—Na2	116.2 (3)	O2—C7—O1—Zn1	−1.6 (5)
C3—C8—O4—Zn1^iv	−175.2 (2)	O2—C7—O1—Na2ⁱ	132.1 (3)
C4—C3—C8—O3	0.9 (5)	O3—C8—O4—Zn1^iv	3.1 (4)
C4—C3—C8—O4	179.3 (3)	O4—C8—O3—Na2	−62.1 (5)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7A···O5^vi	0.82	1.79	2.587 (4)	162
O7—H7B···O12^vii	0.82	1.93	2.740 (4)	172
O8—H8A···O10	0.82	2.40	3.114 (5)	146
O8—H8A···O11	0.82	1.98	2.672 (8)	142
O8—H8B···O6^vii	0.82	2.05	2.641 (5)	128
O9—H9A···O12^viii	0.82	1.95	2.734 (4)	159
O9—H9B···O2^ix	0.82	2.01	2.823 (4)	170
O10—H10A···O5ⁱⁱⁱ	0.82	2.06	2.719 (6)	137
O10—H10B···O9^x	0.82	2.31	3.079 (5)	155
O11—H11A···O3^xi	0.85	2.03	2.835 (8)	157
O11—H11B···O3ⁱⁱⁱ	0.85	2.27	2.866 (7)	127
O11—H11B···O11^xii	0.85	1.33	1.973 (9)	128
O12—H12A···O6	0.82	1.86	2.652 (4)	161
O12—H12B···O4^xiii	0.82	1.97	2.787 (3)	172

Symmetry codes: (iii) −x+1, −y+1, −z+1; (vi) x, y+1, z−1; (vii) −x+1, −y+2, −z+1; (viii) −x+2, −y+2, −z+1; (ix) −x+2, −y+2, −z; (x) x−1, y, z; (xi) x−1, y+1, z; (xii) −x, −y+2, −z+1; (xiii) x, y, z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7A···O5ⁱ	0.82	1.79	2.587 (4)	162
O7—H7B···O12ⁱⁱ	0.82	1.93	2.740 (4)	172
O8—H8A···O10	0.82	2.40	3.114 (5)	146
O8—H8A···O11	0.82	1.98	2.672 (8)	142
O8—H8B···O6ⁱⁱ	0.82	2.05	2.641 (5)	128
O9—H9A···O12ⁱⁱⁱ	0.82	1.95	2.734 (4)	159
O9—H9B···O2^iv	0.82	2.01	2.823 (4)	170
O10—H10A···O5^v	0.82	2.06	2.719 (6)	137
O10—H10B···O9^vi	0.82	2.31	3.079 (5)	155
O11—H11A···O3^vii	0.85	2.03	2.835 (8)	157
O11—H11B···O3^v	0.85	2.27	2.866 (7)	127
O11—H11B···O11^viii	0.85	1.33	1.973 (9)	128
O12—H12A···O6	0.82	1.86	2.652 (4)	161
O12—H12B···O4^ix	0.82	1.97	2.787 (3)	172

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

Acknowledgements

Financial support by the Fundamental Research Funds for the Central Universities (grant Nos. 2011PY128 and 2014PY053) and the National Undergraduate Training Programs for Innovation and Entrepreneurship (grant No. 2015028) of Huazhong Agricultural University are gratefully acknowledged. We thank Dr Y. Qu of HZAU and Dr X. G. Meng of CCNU for their kind assistance with this work.

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Volume 71| Part 7| July 2015| Pages m143-m144

doi:10.1107/S2056989015012001

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