Triaqua­(1,10-phenanthroline-κ2N,N′)(sulfato-κO)zinc(II)

Liu, H.; Qin, H.; Zhang, Y.-J.; Yang, H.-W.; Zhang, J.

doi:10.1107/S1600536811003138

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Pages m280-m281

doi:10.1107/S1600536811003138

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Triaqua(1,10-phenanthroline-κ²N,N′)(sulfato-κO)zinc(II)

Hong Liu,^a ^* Hui Qin,^a Yun-Jie Zhang,^a Hong-Wei Yang ^a and Jian Zhang ^a

^aCollege of Pharmacy, Jiamusi University, Jiamusi, Heilongjiang 154007, People's Republic of China
^*Correspondence e-mail: liuh_2008@yahoo.cn

(Received 19 January 2011; accepted 24 January 2011; online 29 January 2011)

The Zn(II) atom in the title compound, [Zn(SO₄)(C₁₂H₈N₂)(H₂O)₃], is coordinated by one O atom from a sulfate dianion, two N atoms from a 1,10-phenanthroline molecule and three water O atoms in an octahedral geometry. An intramolecular O—H⋯O hydrogen bond occurs. Intermolecular O—H⋯O hydrogen bonds generate a layer structure parallel to (001). There are weak C—H⋯O interactions within the layers.

Related literature

For related structures, see: An et al. (2007 ); Dietz et al. (2009 ); Harvey et al. (2000 ); Hu et al. (2009 ); Zheng et al. (2002 ).

Experimental

Crystal data

[Zn(SO₄)(C₁₂H₈N₂)(H₂O)₃]
M_r = 395.71
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.0011 (4) Å
b = 9.6006 (4) Å
c = 19.1606 (9) Å
V = 1471.83 (12) Å³
Z = 4
Mo Kα radiation
μ = 1.85 mm⁻¹
T = 296 K
0.25 × 0.16 × 0.14 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.710, T_max = 0.785
7397 measured reflections
2793 independent reflections
2667 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.021
wR(F²) = 0.050
S = 1.01
2793 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.36 e Å⁻³
Absolute structure: Flack (1983 ), 1165 Friedel pairs
Flack parameter: 0.005 (9)

Table 1
Selected bond lengths (Å)

Zn—O7	2.0874 (16)
Zn—O5	2.1128 (15)
Zn—O6	2.1175 (16)
Zn—O1	2.1431 (15)
Zn—N2	2.1442 (19)
Zn—N1	2.1605 (19)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H51⋯O2ⁱ	0.87	1.79	2.655 (2)	174
O5—H52⋯O4ⁱⁱ	0.87	1.91	2.775 (2)	172
O6—H61⋯O1ⁱⁱ	0.91	1.93	2.809 (2)	161
O6—H62⋯O3	0.87	1.86	2.688 (2)	158
O7—H71⋯O3ⁱⁱⁱ	0.96	1.85	2.769 (3)	160
O7—H72⋯O4ⁱ	0.83	1.97	2.797 (2)	173
C1—H1⋯O3ⁱⁱⁱ	0.93	2.51	3.416 (3)	165
Symmetry codes: (i) x-1, y, z; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2003 ); cell refinement: SAINT (Bruker, 2001 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Berndt, 1999 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811003138/ng5108sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811003138/ng5108Isup2.hkl

checkCIF report

Comment top

The design and synthesis of 1,10-phenanthroline (phen) and sulfato coordination compounds have drawn considerable attention in the last decade. For the 0D structures of phen and sulfato ligand based transition-metal complexes, see: Zheng et al. (2002); An et al. (2007); Harvey et al. (2000). For the chian structures, see: Dietz et al. (2009); Hu et al. (2009). Among these compounds, the zinc(II) complexes were reported by Harvey et al. (2000) and Hu et al. (2009). We herein report a new phen and sulfato coordinated zinc(II) complex, which presents similar coordiantion style for zinc atom of that reported by Harvey et al. (2000).

The title compound crystallizes in chiral P2₁2₁2₁ space group with three twofold axizes coexisting along a, b and c axies respectively, which is firstly found among the known phen and sulfato ligand based transition-metal complexes. As shown in Fig. 1, the Zn atoms are each surrounded by two N atoms from one phen ligand, four O atoms from three water molecules and one sulfato group to form distorted octahedra. The distances of Zn—N are 2.1591 (19) Å and 2.1449 (19) Å, respectively. The distances of Zn—O are in the range of 2.0881 (17) Å to 2.1443 (15) Å. The complex molecule displays a strong intramolecular hydrogen bond between water O(6) and sulfato O(3) atoms with d(O6···O3) = 2.687 Å. The intermolecular O—H···O hydrogen bonds exist between water molecules and sulfato O atoms and favor the formation of two-dimensional layered supramolecular network along [0 0 1] direction (Fig. 2). There are also weak C—H···O interactions between phen and sulfato O atoms to consolidate the two-dimensional framework. Different to the known phen and sulfato ligand based complexes, the neighboring phen ligands in the title compound do not exist the transparent π—π stacking interactions. This result indicates that solventothermal synthetic procedure may restrain the formation of π—π stacking interactions between neighboring conjugated ligands.

Related literature top

For related structures, see: An et al. (2007); Dietz et al. (2009); Harvey et al. (2000); Hu et al. (2009); Zheng et al. (2002).

Experimental top

A mixture of ZnSO₄ (0.0719 g, 0.25 mmol) and 1,10-phenanthroline (0.0496 g, 0.25 mmol) was dissolved in 8 ml 60% (V:V) ethanol solution and stirred for about an hour. Then it was transferred and sealed in a 15 ml Teflon-lined bomb which was heated at 100 °C for 5 days and cooled to room temperature. Colorless block crystals were collected. Yield: ca. 25% based on Zn. Elementalanalysis (%): Calcd for C₁₂H₁₄N₂O₇SZn: C, 36.42; H, 3.57; N, 7.08; Zn, 16.53. Found: C, 36.04; H, 3.68; N, 7.02; Zn, 16.39.

Computing details top

Data collection: APEX2 (Bruker, 2003); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Berndt, 1999); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The coordiantion feature of the title compound. Dispalcement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A view of two-dimensional layered structures of the title compound (color codes: Zn, cyan; S, yellow; O, red; N, blue; C, grey.). H atoms are omitted for clarity.

Triaqua(1,10-phenanthroline-κ²N,N')(sulfato- κO)zinc(II) top

Crystal data top

[Zn(SO₄)(C₁₂H₈N₂)(H₂O)₃]	F(000) = 808
M_r = 395.71	D_x = 1.786 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1025 reflections
a = 8.0011 (4) Å	θ = 1.5–26.5°
b = 9.6006 (4) Å	µ = 1.85 mm⁻¹
c = 19.1606 (9) Å	T = 296 K
V = 1471.83 (12) Å³	Block, colourless
Z = 4	0.25 × 0.16 × 0.14 mm

Data collection top

Bruker APEXII diffractometer	2793 independent reflections
Radiation source: fine-focus sealed tube	2667 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ω and ϕ scans	θ_max = 26.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.710, T_max = 0.785	k = −11→11
7397 measured reflections	l = −22→23

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)] = 0.021	H-atom parameters constrained
wR(F²) = 0.050	w = 1/[σ²(F_o²) + (0.0161P)² + 0.005P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
2793 reflections	Δρ_max = 0.29 e Å⁻³
208 parameters	Δρ_min = −0.36 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1165 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.005 (9)

Crystal data top

[Zn(SO₄)(C₁₂H₈N₂)(H₂O)₃]	V = 1471.83 (12) Å³
M_r = 395.71	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.0011 (4) Å	µ = 1.85 mm⁻¹
b = 9.6006 (4) Å	T = 296 K
c = 19.1606 (9) Å	0.25 × 0.16 × 0.14 mm

Data collection top

Bruker APEXII diffractometer	2793 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2667 reflections with I > 2σ(I)
T_min = 0.710, T_max = 0.785	R_int = 0.025
7397 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.021	H-atom parameters constrained
wR(F²) = 0.050	Δρ_max = 0.29 e Å⁻³
S = 1.01	Δρ_min = −0.36 e Å⁻³
2793 reflections	Absolute structure: Flack (1983), 1165 Friedel pairs
208 parameters	Absolute structure parameter: 0.005 (9)
0 restraints

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
Zn	0.35962 (3)	0.46528 (2)	0.682343 (13)	0.02381 (7)
S	0.75438 (7)	0.43014 (5)	0.72471 (3)	0.02418 (13)
O1	0.59078 (18)	0.36372 (14)	0.70689 (8)	0.0256 (4)
O2	0.8188 (2)	0.50361 (18)	0.66363 (10)	0.0400 (5)
O3	0.7288 (2)	0.52839 (19)	0.78257 (9)	0.0405 (4)
O4	0.8701 (2)	0.31908 (16)	0.74536 (10)	0.0368 (4)
O5	0.13662 (19)	0.58142 (15)	0.67227 (9)	0.0360 (4)
H51	0.0345	0.5516	0.6719	0.043*
H52	0.1259	0.6578	0.6961	0.043*
O6	0.3974 (2)	0.57293 (15)	0.77750 (9)	0.0323 (4)
H61	0.3775	0.6643	0.7869	0.039*
H62	0.5003	0.5579	0.7908	0.039*
O7	0.2180 (2)	0.31186 (16)	0.73196 (10)	0.0371 (4)
H71	0.2385	0.2140	0.7387	0.044*
H72	0.1156	0.3184	0.7392	0.044*
N1	0.4592 (2)	0.62126 (19)	0.61251 (10)	0.0264 (4)
N2	0.3537 (3)	0.35890 (18)	0.58398 (10)	0.0291 (4)
C1	0.3124 (3)	0.2282 (3)	0.57089 (15)	0.0384 (6)
H1	0.2798	0.1720	0.6080	0.046*
C2	0.3153 (4)	0.1707 (3)	0.50423 (16)	0.0489 (8)
H2	0.2882	0.0775	0.4975	0.059*
C3	0.3584 (4)	0.2526 (3)	0.44882 (16)	0.0491 (7)
H3	0.3586	0.2159	0.4039	0.059*
C4	0.4539 (4)	0.4834 (4)	0.40547 (14)	0.0534 (8)
H4	0.4550	0.4519	0.3596	0.064*
C5	0.5013 (4)	0.6158 (4)	0.41983 (16)	0.0560 (8)
H5	0.5333	0.6740	0.3834	0.067*
C6	0.5501 (4)	0.8055 (3)	0.50634 (16)	0.0513 (8)
H6	0.5799	0.8678	0.4713	0.062*
C7	0.5510 (4)	0.8461 (3)	0.57495 (17)	0.0478 (7)
H7	0.5808	0.9366	0.5870	0.057*
C8	0.5069 (3)	0.7504 (3)	0.62626 (15)	0.0356 (6)
H8	0.5112	0.7786	0.6727	0.043*
C9	0.4024 (3)	0.3920 (3)	0.45999 (14)	0.0385 (6)
C10	0.5032 (4)	0.6680 (3)	0.48954 (14)	0.0401 (6)
C11	0.4028 (3)	0.4397 (2)	0.52967 (12)	0.0270 (5)
C12	0.4559 (3)	0.5801 (2)	0.54475 (13)	0.0274 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn	0.02190 (13)	0.02351 (11)	0.02601 (13)	−0.00085 (10)	−0.00003 (11)	0.00258 (11)
S	0.0178 (3)	0.0195 (2)	0.0353 (3)	−0.00060 (19)	−0.0031 (2)	−0.0023 (2)
O1	0.0160 (7)	0.0222 (7)	0.0387 (10)	−0.0020 (6)	−0.0036 (7)	−0.0028 (6)
O2	0.0267 (9)	0.0472 (11)	0.0462 (11)	−0.0069 (7)	0.0022 (7)	0.0116 (8)
O3	0.0367 (9)	0.0395 (9)	0.0453 (11)	0.0022 (9)	−0.0069 (8)	−0.0196 (9)
O4	0.0234 (8)	0.0299 (8)	0.0570 (11)	0.0054 (7)	−0.0058 (9)	0.0058 (7)
O5	0.0207 (8)	0.0286 (7)	0.0589 (11)	0.0011 (7)	−0.0020 (9)	0.0013 (8)
O6	0.0331 (9)	0.0277 (8)	0.0361 (9)	0.0088 (6)	−0.0016 (7)	−0.0025 (7)
O7	0.0239 (9)	0.0271 (8)	0.0601 (12)	−0.0002 (7)	0.0102 (8)	0.0125 (8)
N1	0.0217 (10)	0.0288 (9)	0.0288 (11)	−0.0013 (8)	0.0015 (8)	0.0004 (8)
N2	0.0267 (10)	0.0287 (8)	0.0317 (10)	−0.0010 (9)	−0.0033 (10)	−0.0012 (8)
C1	0.0392 (16)	0.0324 (12)	0.0436 (16)	−0.0071 (11)	−0.0047 (12)	0.0014 (11)
C2	0.0497 (18)	0.0393 (14)	0.0578 (19)	−0.0062 (13)	−0.0099 (14)	−0.0176 (13)
C3	0.0487 (17)	0.0583 (16)	0.0402 (16)	−0.0022 (15)	−0.0058 (15)	−0.0209 (14)
C4	0.0595 (18)	0.076 (2)	0.0244 (14)	−0.0044 (17)	0.0069 (12)	−0.0032 (14)
C5	0.068 (2)	0.069 (2)	0.0307 (16)	−0.0089 (17)	0.0116 (15)	0.0113 (15)
C6	0.0566 (19)	0.0457 (16)	0.0515 (19)	−0.0135 (14)	0.0086 (15)	0.0187 (14)
C7	0.0550 (18)	0.0332 (13)	0.0553 (19)	−0.0153 (13)	0.0078 (15)	0.0037 (13)
C8	0.0347 (14)	0.0338 (12)	0.0383 (15)	−0.0065 (11)	0.0018 (12)	−0.0044 (11)
C9	0.0332 (15)	0.0476 (14)	0.0347 (14)	0.0019 (11)	−0.0005 (11)	−0.0067 (12)
C10	0.0385 (15)	0.0482 (15)	0.0338 (15)	−0.0037 (13)	0.0085 (12)	0.0071 (12)
C11	0.0206 (11)	0.0342 (12)	0.0262 (12)	0.0019 (9)	0.0003 (9)	−0.0021 (9)
C12	0.0221 (12)	0.0324 (11)	0.0277 (12)	0.0007 (9)	0.0014 (10)	0.0009 (10)

Geometric parameters (Å, º) top

Zn—O7	2.0874 (16)	C1—C2	1.392 (4)
Zn—O5	2.1128 (15)	C1—H1	0.9300
Zn—O6	2.1175 (16)	C2—C3	1.365 (4)
Zn—O1	2.1431 (15)	C2—H2	0.9300
Zn—N2	2.1442 (19)	C3—C9	1.400 (4)
Zn—N1	2.1605 (19)	C3—H3	0.9300
S—O2	1.4605 (18)	C4—C5	1.355 (5)
S—O4	1.4663 (16)	C4—C9	1.425 (4)
S—O3	1.4698 (18)	C4—H4	0.9300
S—O1	1.4955 (15)	C5—C10	1.427 (4)
O5—H51	0.8655	C5—H5	0.9300
O5—H52	0.8678	C6—C7	1.371 (4)
O6—H61	0.9094	C6—C10	1.409 (4)
O6—H62	0.8738	C6—H6	0.9300
O7—H71	0.9628	C7—C8	1.392 (4)
O7—H72	0.8331	C7—H7	0.9300
N1—C8	1.324 (3)	C8—H8	0.9300
N1—C12	1.357 (3)	C9—C11	1.412 (3)
N2—C1	1.322 (3)	C10—C12	1.405 (3)
N2—C11	1.356 (3)	C11—C12	1.442 (3)

O7—Zn—O5	87.46 (6)	N2—C1—C2	123.1 (3)
O7—Zn—O6	91.71 (7)	N2—C1—H1	118.4
O5—Zn—O6	86.66 (6)	C2—C1—H1	118.4
O7—Zn—O1	92.72 (6)	C3—C2—C1	119.3 (2)
O5—Zn—O1	171.49 (6)	C3—C2—H2	120.3
O6—Zn—O1	84.83 (6)	C1—C2—H2	120.3
O7—Zn—N2	92.99 (7)	C2—C3—C9	119.7 (3)
O5—Zn—N2	98.77 (7)	C2—C3—H3	120.2
O6—Zn—N2	172.97 (7)	C9—C3—H3	120.2
O1—Zn—N2	89.73 (7)	C5—C4—C9	120.7 (3)
O7—Zn—N1	166.26 (7)	C5—C4—H4	119.7
O5—Zn—N1	83.64 (6)	C9—C4—H4	119.7
O6—Zn—N1	98.18 (7)	C4—C5—C10	121.5 (3)
O1—Zn—N1	97.64 (6)	C4—C5—H5	119.2
N2—Zn—N1	78.11 (7)	C10—C5—H5	119.2
O2—S—O4	110.15 (10)	C7—C6—C10	119.2 (3)
O2—S—O3	110.09 (11)	C7—C6—H6	120.4
O4—S—O3	110.55 (11)	C10—C6—H6	120.4
O2—S—O1	109.39 (10)	C6—C7—C8	119.2 (3)
O4—S—O1	107.69 (9)	C6—C7—H7	120.4
O3—S—O1	108.91 (10)	C8—C7—H7	120.4
S—O1—Zn	127.69 (8)	N1—C8—C7	123.5 (3)
Zn—O5—H51	128.6	N1—C8—H8	118.3
Zn—O5—H52	118.8	C7—C8—H8	118.3
H51—O5—H52	101.0	C3—C9—C11	117.1 (2)
Zn—O6—H61	128.0	C3—C9—C4	123.3 (3)
Zn—O6—H62	107.7	C11—C9—C4	119.5 (2)
H61—O6—H62	105.5	C12—C10—C6	117.5 (2)
Zn—O7—H71	131.1	C12—C10—C5	119.4 (3)
Zn—O7—H72	123.8	C6—C10—C5	123.1 (3)
H71—O7—H72	102.6	N2—C11—C9	122.6 (2)
C8—N1—C12	118.0 (2)	N2—C11—C12	117.8 (2)
C8—N1—Zn	129.22 (18)	C9—C11—C12	119.6 (2)
C12—N1—Zn	112.53 (14)	N1—C12—C10	122.7 (2)
C1—N2—C11	118.0 (2)	N1—C12—C11	118.0 (2)
C1—N2—Zn	128.65 (18)	C10—C12—C11	119.3 (2)
C11—N2—Zn	113.30 (14)

O2—S—O1—Zn	−66.81 (14)	C12—N1—C8—C7	1.1 (4)
O4—S—O1—Zn	173.47 (11)	Zn—N1—C8—C7	−172.2 (2)
O3—S—O1—Zn	53.56 (15)	C6—C7—C8—N1	−1.8 (5)
O7—Zn—O1—S	−144.44 (12)	C2—C3—C9—C11	1.3 (4)
O6—Zn—O1—S	−52.97 (12)	C2—C3—C9—C4	178.0 (3)
N2—Zn—O1—S	122.58 (13)	C5—C4—C9—C3	−177.4 (3)
N1—Zn—O1—S	44.62 (13)	C5—C4—C9—C11	−0.8 (4)
O7—Zn—N1—C8	127.7 (3)	C7—C6—C10—C12	1.4 (4)
O5—Zn—N1—C8	77.8 (2)	C7—C6—C10—C5	−178.9 (3)
O6—Zn—N1—C8	−7.9 (2)	C4—C5—C10—C12	0.4 (5)
O1—Zn—N1—C8	−93.7 (2)	C4—C5—C10—C6	−179.3 (3)
N2—Zn—N1—C8	178.2 (2)	C1—N2—C11—C9	3.6 (3)
O7—Zn—N1—C12	−45.9 (4)	Zn—N2—C11—C9	−177.59 (18)
O5—Zn—N1—C12	−95.77 (15)	C1—N2—C11—C12	−176.9 (2)
O6—Zn—N1—C12	178.55 (15)	Zn—N2—C11—C12	1.9 (3)
O1—Zn—N1—C12	92.71 (15)	C3—C9—C11—N2	−3.9 (4)
N2—Zn—N1—C12	4.61 (15)	C4—C9—C11—N2	179.3 (2)
O7—Zn—N2—C1	−15.4 (2)	C3—C9—C11—C12	176.6 (2)
O5—Zn—N2—C1	−103.3 (2)	C4—C9—C11—C12	−0.2 (4)
O1—Zn—N2—C1	77.3 (2)	C8—N1—C12—C10	1.0 (3)
N1—Zn—N2—C1	175.2 (2)	Zn—N1—C12—C10	175.37 (19)
O7—Zn—N2—C11	165.96 (15)	C8—N1—C12—C11	−179.6 (2)
O5—Zn—N2—C11	78.08 (16)	Zn—N1—C12—C11	−5.2 (2)
O1—Zn—N2—C11	−101.33 (16)	C6—C10—C12—N1	−2.2 (4)
N1—Zn—N2—C11	−3.46 (15)	C5—C10—C12—N1	178.1 (3)
C11—N2—C1—C2	−0.7 (4)	C6—C10—C12—C11	178.4 (3)
Zn—N2—C1—C2	−179.3 (2)	C5—C10—C12—C11	−1.3 (4)
N2—C1—C2—C3	−1.8 (5)	N2—C11—C12—N1	2.3 (3)
C1—C2—C3—C9	1.4 (5)	C9—C11—C12—N1	−178.2 (2)
C9—C4—C5—C10	0.7 (5)	N2—C11—C12—C10	−178.2 (2)
C10—C6—C7—C8	0.4 (5)	C9—C11—C12—C10	1.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H51···O2ⁱ	0.87	1.79	2.655 (2)	174
O5—H52···O4ⁱⁱ	0.87	1.91	2.775 (2)	172
O6—H61···O1ⁱⁱ	0.91	1.93	2.809 (2)	161
O6—H62···O3	0.87	1.86	2.688 (2)	158
O7—H71···O3ⁱⁱⁱ	0.96	1.85	2.769 (3)	160
O7—H72···O4ⁱ	0.83	1.97	2.797 (2)	173
C1—H1···O3ⁱⁱⁱ	0.93	2.51	3.416 (3)	165

Symmetry codes: (i) x−1, y, z; (ii) −x+1, y+1/2, −z+3/2; (iii) −x+1, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	[Zn(SO₄)(C₁₂H₈N₂)(H₂O)₃]
M_r	395.71
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	8.0011 (4), 9.6006 (4), 19.1606 (9)
V (Å³)	1471.83 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.85
Crystal size (mm)	0.25 × 0.16 × 0.14

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.710, 0.785
No. of measured, independent and observed [I > 2σ(I)] reflections	7397, 2793, 2667
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.021, 0.050, 1.01
No. of reflections	2793
No. of parameters	208
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.36
Absolute structure	Flack (1983), 1165 Friedel pairs
Absolute structure parameter	0.005 (9)

Computer programs: APEX2 (Bruker, 2003), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Berndt, 1999).

Selected bond lengths (Å) top

Zn—O7	2.0874 (16)	Zn—O1	2.1431 (15)
Zn—O5	2.1128 (15)	Zn—N2	2.1442 (19)
Zn—O6	2.1175 (16)	Zn—N1	2.1605 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H51···O2ⁱ	0.87	1.79	2.655 (2)	174
O5—H52···O4ⁱⁱ	0.87	1.91	2.775 (2)	172
O6—H61···O1ⁱⁱ	0.91	1.93	2.809 (2)	161
O6—H62···O3	0.87	1.86	2.688 (2)	158
O7—H71···O3ⁱⁱⁱ	0.96	1.85	2.769 (3)	160
O7—H72···O4ⁱ	0.83	1.97	2.797 (2)	173
C1—H1···O3ⁱⁱⁱ	0.93	2.51	3.416 (3)	165

Symmetry codes: (i) x−1, y, z; (ii) −x+1, y+1/2, −z+3/2; (iii) −x+1, y−1/2, −z+3/2.

Acknowledgements

The project was supported by the Natural Science Foundation of Heilongjiang Province (No. B200917 and B200901), the Education Office Foundation of Heilongjiang Province (No. 11551484), the Foundation of Jiamusi University (No. Szj2008–017), the Sci. & Tech. Project of Heilongjiang Province (2009 G1099–00) and the Doctoral Foundation of Material Science Key Dicipline of Jiamusi University (No. E08050207).

References

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