Aqua(4-hydroxy­benzoato-κO)(4-hydroxy­benzoato-κ2O,O′)(1,10-phenanthroline-κ2N,N′)zinc(II) monohydrate

Kong, L.-L.; Gao, S.; Huo, L.-H.; Ng, S.W.

doi:10.1107/S1600536808002249

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page m422

doi:10.1107/S1600536808002249

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Aqua(4-hydroxybenzoato-κO)(4-hydroxybenzoato-κ²O,O′)(1,10-phenanthroline-κ²N,N′)zinc(II) monohydrate

Li-Li Kong,^a Shan Gao,^a Li-Hua Huo ^a and Seik Weng Ng ^b ^*

^aSchool of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 7 January 2008; accepted 21 January 2008; online 25 January 2008)

The Zn atom in the title compound, [Zn(C₇H₅O₃)₂(C₁₂H₈N₂)(H₂O)]·H₂O, exists in a distorted cis-ZnN₂O₄ octahedral coordination geometry. One of the 4-hydroxybenzoate anions chelates in a bidentate manner whereas the other is monodentate. The complex molecules are linked through the uncoordinated water molecules into a hydrogen-bonded sheet structure.

Related literature

For related zinc bis(4-hydroxybenzoate) structures containing an N-heterocycle, see: Hökelek & Necefouglu (1996 ); Nadzhafov et al. (1981 ); Necefoğlu et al. (2002 ); Wang & Okabe (2005 ); Zheng et al. (2006 ).

Experimental

Crystal data

[Zn(C₇H₅O₃)₂(C₁₂H₈N₂)(H₂O)]·H₂O
M_r = 555.83
Monoclinic, P 2₁ /c
a = 11.1169 (5) Å
b = 19.738 (1) Å
c = 11.5503 (6) Å
β = 106.298 (1)°
V = 2432.5 (2) Å³
Z = 4
Mo Kα radiation
μ = 1.06 mm⁻¹
T = 295 (2) K
0.30 × 0.24 × 0.18 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.674, T_max = 0.832
23098 measured reflections
5541 independent reflections
3924 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.131
S = 1.08
5541 reflections
336 parameters
H-atom parameters constrained
Δρ_max = 0.67 e Å⁻³
Δρ_min = −0.88 e Å⁻³

Table 1
Selected bond lengths (Å)

Zn1—O1	2.025 (2)
Zn1—O2	2.470 (2)
Zn1—O4	2.069 (2)
Zn1—O1w	2.143 (2)
Zn1—N1	2.075 (2)
Zn1—N2	2.155 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3o⋯O2ⁱ	0.85	1.81	2.619 (3)	157
O6—H6o⋯O4ⁱⁱ	0.85	1.90	2.742 (3)	171
O1w—H1w1⋯O2wⁱⁱⁱ	0.85	2.01	2.819 (4)	158
O1w—H1w2⋯O5	0.85	1.84	2.599 (3)	148
O2w—H2w1⋯O5	0.85	2.04	2.801 (4)	148
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) -x+1, -y+1, -z+1.

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2008 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808002249/hb2688sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808002249/hb2688Isup2.hkl

checkCIF report

Comment top

The title compound, (I), extends the range of adducts of zinc bis(4-hydroxybenzoate) with N-heterocycles: For the N,N-diethylnicotinamide adduct, see: Hökelek & Necefouglu (1996). For the pyridine adduct, see; Nadzhafov et al. (1981). For the nicotinamide adduct, see: Necefoğlu et al. (2002). For the bis(2-pyridyl)amine adduct, see: Wang & Okabe (2005). For the benzimidazole adduct, see: Zheng et al. (2006).

The Zn atom in (I) adopts a distorted cis-ZnN₂O₄ coordination geometry. One of the 4-hydroxybenzoate anions chelates in an anisobidentate manner whereas the other is unidentate (Table 1, Fig. 1).

In the crystal, the complex molecules are linked through the uncoordinated water molecules into a hydrogen-bonded sheet structure (Table 2).

Related literature top

For related zinc bis(4-hydroxybenzoate) structures containing an N-heterocycle, see: Hökelek & Necefouglu (1996); Nadzhafov et al. (1981); Necefoğlu et al. (2002); Wang & Okabe (2005); Zheng et al. (2006).

Experimental top

Zinc diacetate dihydrate (1 mmol), 1,10-phenanthroline (2 mmol) and 4-hydroxybenzoic acid (2 mmol) were dissolved in aqueous ethanol Colourless blocks of (I) were isolated after several days.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).

Figures top

Fig. 1. View of the molecular structure of (I) with displacement ellipsoids drawn at the 50% probability level (H atoms drawn as spheres of arbitrary radius).

Aquabis(4-hydroxybenzoato-κO)(4-hydroxybenzoato-κ²O,O')(1,10- phenanthroline-κ²N,N')zinc(II) monohydrate top

Crystal data top

[Zn(C₇H₅O₃)₂(C₁₂H₈N₂)(H₂O)]·H₂O	F(000) = 1144
M_r = 555.83	D_x = 1.518 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 10359 reflections
a = 11.1169 (5) Å	θ = 3.1–27.5°
b = 19.738 (1) Å	µ = 1.06 mm⁻¹
c = 11.5503 (6) Å	T = 295 K
β = 106.298 (1)°	Block, colorless
V = 2432.5 (2) Å³	0.30 × 0.24 × 0.18 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	5541 independent reflections
Radiation source: fine-focus sealed tube	3924 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
Detector resolution: 10.000 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
ω scans	h = −14→14
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −25→25
T_min = 0.674, T_max = 0.832	l = −14→14
23098 measured 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.131	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0632P)² + 0.8555P] where P = (F_o² + 2F_c²)/3
5541 reflections	(Δ/σ)_max = 0.001
336 parameters	Δρ_max = 0.67 e Å⁻³
0 restraints	Δρ_min = −0.88 e Å⁻³

Crystal data top

[Zn(C₇H₅O₃)₂(C₁₂H₈N₂)(H₂O)]·H₂O	V = 2432.5 (2) Å³
M_r = 555.83	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.1169 (5) Å	µ = 1.06 mm⁻¹
b = 19.738 (1) Å	T = 295 K
c = 11.5503 (6) Å	0.30 × 0.24 × 0.18 mm
β = 106.298 (1)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	5541 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3924 reflections with I > 2σ(I)
T_min = 0.674, T_max = 0.832	R_int = 0.036
23098 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.131	H-atom parameters constrained
S = 1.08	Δρ_max = 0.67 e Å⁻³
5541 reflections	Δρ_min = −0.88 e Å⁻³
336 parameters

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

	x	y	z	U_iso*/U_eq
Zn1	0.23086 (3)	0.517846 (16)	0.72570 (3)	0.05090 (13)
O1	0.2083 (2)	0.43474 (11)	0.6190 (2)	0.0681 (6)
O2	0.2863 (2)	0.40272 (11)	0.8070 (2)	0.0663 (6)
O3	0.3803 (2)	0.13818 (12)	0.5298 (2)	0.0729 (6)
H3o	0.3548	0.1357	0.4533	0.109*
O4	0.19613 (18)	0.60020 (9)	0.61024 (17)	0.0507 (4)
O5	0.3820 (2)	0.61864 (13)	0.5776 (2)	0.0725 (6)
O6	0.03862 (19)	0.81782 (11)	0.19250 (19)	0.0612 (5)
H6o	0.0924	0.8392	0.1669	0.092*
O1w	0.4267 (2)	0.52299 (12)	0.7387 (2)	0.0749 (7)
H1w1	0.4483	0.4874	0.7080	0.112*
H1w2	0.4409	0.5576	0.7007	0.112*
O2w	0.5117 (3)	0.5725 (2)	0.4171 (4)	0.1517 (16)
H2w1	0.4623	0.5704	0.4614	0.182*
H2w2	0.4914	0.6047	0.3664	0.182*
N1	0.2575 (2)	0.55676 (12)	0.8980 (2)	0.0524 (6)
N2	0.0408 (2)	0.52319 (11)	0.7369 (2)	0.0478 (5)
C1	0.2581 (3)	0.38959 (15)	0.6961 (3)	0.0555 (7)
C2	0.2870 (3)	0.32281 (14)	0.6520 (3)	0.0498 (6)
C3	0.2367 (3)	0.30452 (15)	0.5320 (3)	0.0559 (7)
H3	0.1830	0.3342	0.4795	0.067*
C4	0.2653 (3)	0.24292 (16)	0.4895 (3)	0.0589 (7)
H4	0.2291	0.2308	0.4095	0.071*
C5	0.3479 (3)	0.19928 (15)	0.5664 (3)	0.0549 (7)
C6	0.4005 (3)	0.21700 (15)	0.6863 (3)	0.0574 (7)
H6	0.4563	0.1879	0.7381	0.069*
C7	0.3693 (3)	0.27787 (15)	0.7279 (3)	0.0555 (7)
H7	0.4039	0.2893	0.8085	0.067*
C8	0.2667 (3)	0.62967 (14)	0.5549 (3)	0.0495 (6)
C9	0.2074 (3)	0.67968 (14)	0.4592 (2)	0.0480 (6)
C10	0.0776 (3)	0.68671 (15)	0.4180 (3)	0.0539 (7)
H10	0.0269	0.6598	0.4508	0.065*
C11	0.0234 (3)	0.73289 (16)	0.3295 (3)	0.0562 (7)
H11	−0.0634	0.7370	0.3031	0.067*
C12	0.0982 (3)	0.77342 (14)	0.2796 (2)	0.0509 (6)
C13	0.2280 (3)	0.76739 (15)	0.3202 (3)	0.0562 (7)
H13	0.2786	0.7945	0.2874	0.067*
C14	0.2815 (3)	0.72096 (14)	0.4094 (3)	0.0543 (7)
H14	0.3683	0.7172	0.4366	0.065*
C15	0.1503 (3)	0.56991 (13)	0.9281 (2)	0.0501 (6)
C16	0.3666 (3)	0.57100 (18)	0.9768 (3)	0.0701 (9)
H16	0.4399	0.5617	0.9560	0.084*
C17	0.3757 (4)	0.5985 (2)	1.0862 (4)	0.0874 (12)
H17	0.4542	0.6070	1.1392	0.105*
C18	0.2708 (5)	0.6137 (2)	1.1192 (3)	0.0868 (12)
H18	0.2774	0.6333	1.1940	0.104*
C19	0.1501 (4)	0.59957 (16)	1.0383 (3)	0.0669 (9)
C20	0.0339 (5)	0.61090 (19)	1.0621 (4)	0.0853 (12)
H20	0.0331	0.6306	1.1350	0.102*
C21	−0.0760 (4)	0.5941 (2)	0.9824 (4)	0.0843 (12)
H21	−0.1505	0.6015	1.0022	0.101*
C22	−0.0799 (3)	0.56479 (16)	0.8669 (3)	0.0640 (8)
C23	−0.1891 (4)	0.5470 (2)	0.7791 (4)	0.0847 (12)
H23	−0.2668	0.5547	0.7923	0.102*
C24	−0.1823 (4)	0.5185 (2)	0.6742 (4)	0.0856 (12)
H24	−0.2551	0.5069	0.6150	0.103*
C25	−0.0643 (3)	0.50667 (18)	0.6557 (3)	0.0654 (8)
H25	−0.0604	0.4866	0.5840	0.078*
C26	0.0332 (3)	0.55205 (13)	0.8411 (2)	0.0472 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0592 (2)	0.0422 (2)	0.0576 (2)	0.00058 (14)	0.02675 (17)	0.00114 (14)
O1	0.0915 (16)	0.0451 (11)	0.0708 (14)	0.0159 (11)	0.0279 (12)	0.0032 (10)
O2	0.0923 (16)	0.0487 (12)	0.0629 (13)	0.0041 (11)	0.0302 (12)	−0.0055 (10)
O3	0.0831 (16)	0.0597 (13)	0.0764 (14)	0.0212 (12)	0.0235 (13)	−0.0112 (12)
O4	0.0592 (11)	0.0410 (10)	0.0603 (11)	0.0033 (8)	0.0306 (9)	0.0069 (8)
O5	0.0613 (13)	0.0814 (16)	0.0829 (15)	0.0100 (12)	0.0336 (12)	0.0261 (13)
O6	0.0682 (13)	0.0559 (12)	0.0626 (12)	−0.0031 (10)	0.0232 (10)	0.0126 (10)
O1w	0.0624 (14)	0.0749 (16)	0.0959 (18)	0.0095 (11)	0.0359 (13)	0.0233 (13)
O2w	0.140 (3)	0.187 (4)	0.162 (3)	−0.004 (3)	0.099 (3)	−0.052 (3)
N1	0.0549 (14)	0.0441 (13)	0.0575 (13)	−0.0065 (10)	0.0145 (12)	−0.0008 (11)
N2	0.0518 (13)	0.0453 (12)	0.0484 (12)	−0.0067 (10)	0.0174 (11)	0.0025 (10)
C1	0.0639 (17)	0.0443 (15)	0.0639 (18)	−0.0001 (13)	0.0271 (15)	0.0002 (14)
C2	0.0550 (15)	0.0416 (14)	0.0586 (16)	0.0015 (12)	0.0257 (13)	0.0001 (12)
C3	0.0608 (17)	0.0522 (17)	0.0568 (16)	0.0093 (14)	0.0200 (14)	0.0030 (13)
C4	0.0648 (18)	0.0591 (18)	0.0544 (16)	0.0071 (15)	0.0193 (15)	−0.0058 (14)
C5	0.0582 (16)	0.0458 (15)	0.0656 (18)	0.0065 (13)	0.0254 (14)	−0.0047 (14)
C6	0.0605 (17)	0.0492 (16)	0.0620 (17)	0.0121 (13)	0.0162 (14)	0.0017 (14)
C7	0.0614 (17)	0.0499 (16)	0.0568 (16)	0.0013 (13)	0.0193 (14)	−0.0018 (13)
C8	0.0573 (16)	0.0418 (14)	0.0552 (15)	−0.0020 (12)	0.0254 (14)	−0.0023 (12)
C9	0.0580 (16)	0.0409 (14)	0.0505 (14)	−0.0050 (12)	0.0244 (13)	−0.0025 (12)
C10	0.0591 (17)	0.0531 (16)	0.0557 (16)	−0.0110 (13)	0.0263 (14)	0.0028 (13)
C11	0.0554 (16)	0.0565 (17)	0.0588 (17)	−0.0053 (13)	0.0197 (14)	0.0047 (14)
C12	0.0654 (17)	0.0408 (14)	0.0511 (15)	−0.0042 (12)	0.0241 (14)	−0.0017 (12)
C13	0.0648 (18)	0.0468 (15)	0.0663 (18)	−0.0070 (13)	0.0336 (15)	0.0051 (14)
C14	0.0562 (16)	0.0483 (16)	0.0630 (17)	−0.0055 (13)	0.0242 (14)	0.0016 (13)
C15	0.0711 (18)	0.0350 (13)	0.0475 (14)	−0.0020 (12)	0.0220 (14)	0.0025 (11)
C16	0.068 (2)	0.065 (2)	0.071 (2)	−0.0107 (17)	0.0100 (17)	−0.0038 (17)
C17	0.089 (3)	0.088 (3)	0.077 (2)	−0.018 (2)	0.009 (2)	−0.005 (2)
C18	0.136 (4)	0.065 (2)	0.0498 (18)	−0.021 (2)	0.011 (2)	−0.0128 (16)
C19	0.105 (3)	0.0459 (17)	0.0577 (18)	0.0020 (17)	0.0366 (19)	−0.0015 (14)
C20	0.138 (4)	0.063 (2)	0.071 (2)	0.011 (2)	0.055 (3)	−0.0033 (18)
C21	0.105 (3)	0.068 (2)	0.108 (3)	0.026 (2)	0.076 (3)	0.017 (2)
C22	0.0641 (19)	0.0555 (18)	0.082 (2)	0.0096 (15)	0.0358 (18)	0.0179 (16)
C23	0.062 (2)	0.085 (3)	0.115 (3)	0.0119 (19)	0.039 (2)	0.032 (3)
C24	0.056 (2)	0.092 (3)	0.099 (3)	−0.0126 (19)	0.005 (2)	0.020 (2)
C25	0.069 (2)	0.066 (2)	0.0607 (18)	−0.0145 (16)	0.0163 (16)	0.0010 (15)
C26	0.0586 (16)	0.0359 (13)	0.0534 (15)	0.0016 (11)	0.0259 (13)	0.0065 (11)

Geometric parameters (Å, º) top

Zn1—O1	2.025 (2)	C7—H7	0.9300
Zn1—O2	2.470 (2)	C8—C9	1.490 (4)
Zn1—O4	2.069 (2)	C9—C14	1.392 (4)
Zn1—O1w	2.143 (2)	C9—C10	1.394 (4)
Zn1—N1	2.075 (2)	C10—C11	1.376 (4)
Zn1—N2	2.155 (2)	C10—H10	0.9300
O1—C1	1.272 (4)	C11—C12	1.391 (4)
O2—C1	1.257 (4)	C11—H11	0.9300
O3—C5	1.359 (3)	C12—C13	1.392 (4)
O3—H3o	0.8501	C13—C14	1.383 (4)
O4—C8	1.282 (3)	C13—H13	0.9300
O5—C8	1.253 (3)	C14—H14	0.9300
O6—C12	1.358 (3)	C15—C19	1.402 (4)
O6—H6o	0.8501	C15—C26	1.447 (4)
O1w—H1w1	0.8500	C16—C17	1.353 (6)
O1w—H1w2	0.8501	C16—H16	0.9300
O2w—H2w1	0.8499	C17—C18	1.358 (6)
O2w—H2w2	0.8500	C17—H17	0.9300
N1—C16	1.326 (4)	C18—C19	1.431 (5)
N1—C15	1.357 (4)	C18—H18	0.9300
N2—C25	1.318 (4)	C19—C20	1.412 (6)
N2—C26	1.356 (3)	C20—C21	1.349 (6)
C1—C2	1.481 (4)	C20—H20	0.9300
C2—C3	1.388 (4)	C21—C22	1.443 (5)
C2—C7	1.394 (4)	C21—H21	0.9300
C3—C4	1.381 (4)	C22—C23	1.391 (5)
C3—H3	0.9300	C22—C26	1.394 (4)
C4—C5	1.384 (4)	C23—C24	1.357 (6)
C4—H4	0.9300	C23—H23	0.9300
C5—C6	1.389 (4)	C24—C25	1.406 (6)
C6—C7	1.374 (4)	C24—H24	0.9300
C6—H6	0.9300	C25—H25	0.9300

O1—Zn1—O4	105.98 (8)	O4—C8—C9	117.7 (2)
O1—Zn1—N1	147.52 (9)	C14—C9—C10	118.4 (3)
O4—Zn1—N1	106.14 (8)	C14—C9—C8	120.3 (3)
O1—Zn1—O1w	91.75 (10)	C10—C9—C8	121.3 (2)
O4—Zn1—O1w	90.57 (8)	C11—C10—C9	121.1 (3)
N1—Zn1—O1w	92.66 (10)	C11—C10—H10	119.5
O1—Zn1—N2	96.91 (9)	C9—C10—H10	119.5
O4—Zn1—N2	89.51 (8)	C10—C11—C12	120.0 (3)
N1—Zn1—N2	78.65 (9)	C10—C11—H11	120.0
O1w—Zn1—N2	170.97 (10)	C12—C11—H11	120.0
O1—Zn1—O2	57.39 (8)	O6—C12—C11	117.0 (3)
O4—Zn1—O2	161.68 (7)	O6—C12—C13	123.3 (3)
N1—Zn1—O2	91.30 (8)	C11—C12—C13	119.7 (3)
O1w—Zn1—O2	82.91 (8)	C14—C13—C12	119.7 (3)
N2—Zn1—O2	99.59 (8)	C14—C13—H13	120.1
C1—O1—Zn1	100.74 (19)	C12—C13—H13	120.1
C1—O2—Zn1	80.68 (17)	C13—C14—C9	121.1 (3)
C5—O3—H3o	109.5	C13—C14—H14	119.5
C8—O4—Zn1	130.40 (18)	C9—C14—H14	119.5
C12—O6—H6o	109.5	N1—C15—C19	122.5 (3)
Zn1—O1w—H1w1	109.4	N1—C15—C26	117.3 (2)
Zn1—O1w—H1w2	109.5	C19—C15—C26	120.1 (3)
H1w1—O1w—H1w2	109.5	N1—C16—C17	122.7 (4)
H2w1—O2w—H2w2	111.0	N1—C16—H16	118.7
C16—N1—C15	118.9 (3)	C17—C16—H16	118.7
C16—N1—Zn1	126.4 (2)	C16—C17—C18	120.4 (4)
C15—N1—Zn1	114.65 (18)	C16—C17—H17	119.8
C25—N2—C26	118.2 (3)	C18—C17—H17	119.8
C25—N2—Zn1	129.3 (2)	C17—C18—C19	119.6 (3)
C26—N2—Zn1	112.33 (18)	C17—C18—H18	120.2
O2—C1—O1	120.3 (3)	C19—C18—H18	120.2
O2—C1—C2	121.2 (3)	C15—C19—C20	118.5 (3)
O1—C1—C2	118.5 (3)	C15—C19—C18	115.8 (3)
O2—C1—Zn1	70.63 (16)	C20—C19—C18	125.7 (3)
O1—C1—Zn1	50.35 (14)	C21—C20—C19	122.1 (3)
C2—C1—Zn1	164.2 (2)	C21—C20—H20	118.9
C3—C2—C7	118.2 (3)	C19—C20—H20	118.9
C3—C2—C1	120.6 (3)	C20—C21—C22	121.0 (3)
C7—C2—C1	121.2 (3)	C20—C21—H21	119.5
C4—C3—C2	121.0 (3)	C22—C21—H21	119.5
C4—C3—H3	119.5	C23—C22—C26	117.0 (3)
C2—C3—H3	119.5	C23—C22—C21	124.7 (3)
C3—C4—C5	119.8 (3)	C26—C22—C21	118.3 (3)
C3—C4—H4	120.1	C24—C23—C22	120.0 (3)
C5—C4—H4	120.1	C24—C23—H23	120.0
O3—C5—C4	122.6 (3)	C22—C23—H23	120.0
O3—C5—C6	117.3 (3)	C23—C24—C25	119.5 (4)
C4—C5—C6	120.0 (3)	C23—C24—H24	120.2
C7—C6—C5	119.5 (3)	C25—C24—H24	120.2
C7—C6—H6	120.3	N2—C25—C24	122.0 (4)
C5—C6—H6	120.3	N2—C25—H25	119.0
C6—C7—C2	121.5 (3)	C24—C25—H25	119.0
C6—C7—H7	119.3	N2—C26—C22	123.4 (3)
C2—C7—H7	119.3	N2—C26—C15	116.8 (2)
O5—C8—O4	123.4 (3)	C22—C26—C15	119.8 (3)
O5—C8—C9	118.9 (2)

O4—Zn1—O1—C1	166.06 (18)	C1—C2—C7—C6	−177.4 (3)
N1—Zn1—O1—C1	−22.8 (3)	Zn1—O4—C8—O5	−11.7 (4)
O1w—Zn1—O1—C1	75.0 (2)	Zn1—O4—C8—C9	168.48 (17)
N2—Zn1—O1—C1	−102.5 (2)	O5—C8—C9—C14	−9.9 (4)
O2—Zn1—O1—C1	−5.47 (18)	O4—C8—C9—C14	169.9 (3)
O1—Zn1—O2—C1	5.51 (18)	O5—C8—C9—C10	170.5 (3)
O4—Zn1—O2—C1	−21.3 (3)	O4—C8—C9—C10	−9.7 (4)
N1—Zn1—O2—C1	176.32 (19)	C14—C9—C10—C11	0.5 (4)
O1w—Zn1—O2—C1	−91.16 (19)	C8—C9—C10—C11	−179.9 (3)
N2—Zn1—O2—C1	97.61 (19)	C9—C10—C11—C12	0.1 (5)
O1—Zn1—O4—C8	−80.1 (2)	C10—C11—C12—O6	179.9 (3)
N1—Zn1—O4—C8	104.8 (2)	C10—C11—C12—C13	−0.5 (4)
O1w—Zn1—O4—C8	11.9 (2)	O6—C12—C13—C14	179.9 (3)
N2—Zn1—O4—C8	−177.1 (2)	C11—C12—C13—C14	0.3 (4)
O2—Zn1—O4—C8	−56.9 (4)	C12—C13—C14—C9	0.3 (5)
C1—Zn1—O4—C8	−70.8 (3)	C10—C9—C14—C13	−0.7 (4)
O1—Zn1—N1—C16	92.9 (3)	C8—C9—C14—C13	179.7 (3)
O4—Zn1—N1—C16	−95.9 (3)	C16—N1—C15—C19	1.6 (4)
O1w—Zn1—N1—C16	−4.6 (3)	Zn1—N1—C15—C19	−176.6 (2)
N2—Zn1—N1—C16	177.9 (3)	C16—N1—C15—C26	−178.4 (3)
O2—Zn1—N1—C16	78.4 (3)	Zn1—N1—C15—C26	3.4 (3)
C1—Zn1—N1—C16	80.4 (3)	C15—N1—C16—C17	−0.3 (5)
O1—Zn1—N1—C15	−89.0 (3)	Zn1—N1—C16—C17	177.7 (3)
O4—Zn1—N1—C15	82.14 (19)	N1—C16—C17—C18	−1.0 (6)
O1w—Zn1—N1—C15	173.51 (19)	C16—C17—C18—C19	1.0 (6)
N2—Zn1—N1—C15	−4.01 (18)	N1—C15—C19—C20	−179.6 (3)
O2—Zn1—N1—C15	−103.54 (19)	C26—C15—C19—C20	0.5 (4)
C1—Zn1—N1—C15	−101.5 (2)	N1—C15—C19—C18	−1.5 (4)
O1—Zn1—N2—C25	−33.1 (3)	C26—C15—C19—C18	178.5 (3)
O4—Zn1—N2—C25	73.0 (3)	C17—C18—C19—C15	0.2 (5)
N1—Zn1—N2—C25	179.5 (3)	C17—C18—C19—C20	178.1 (4)
O2—Zn1—N2—C25	−91.1 (3)	C15—C19—C20—C21	0.1 (5)
C1—Zn1—N2—C25	−62.0 (3)	C18—C19—C20—C21	−177.8 (4)
O1—Zn1—N2—C26	151.55 (17)	C19—C20—C21—C22	−1.4 (6)
O4—Zn1—N2—C26	−102.41 (18)	C20—C21—C22—C23	−178.9 (4)
N1—Zn1—N2—C26	4.16 (17)	C20—C21—C22—C26	2.2 (5)
O2—Zn1—N2—C26	93.56 (17)	C26—C22—C23—C24	0.2 (5)
C1—Zn1—N2—C26	122.68 (18)	C21—C22—C23—C24	−178.7 (4)
Zn1—O2—C1—O1	−8.6 (3)	C22—C23—C24—C25	0.5 (6)
Zn1—O2—C1—C2	168.4 (3)	C26—N2—C25—C24	0.4 (5)
Zn1—O1—C1—O2	10.5 (3)	Zn1—N2—C25—C24	−174.8 (2)
Zn1—O1—C1—C2	−166.6 (2)	C23—C24—C25—N2	−0.8 (6)
O2—C1—C2—C3	168.8 (3)	C25—N2—C26—C22	0.3 (4)
O1—C1—C2—C3	−14.2 (4)	Zn1—N2—C26—C22	176.3 (2)
O2—C1—C2—C7	−14.0 (4)	C25—N2—C26—C15	−179.7 (3)
O1—C1—C2—C7	163.1 (3)	Zn1—N2—C26—C15	−3.7 (3)
C7—C2—C3—C4	1.3 (4)	C23—C22—C26—N2	−0.6 (4)
C1—C2—C3—C4	178.7 (3)	C21—C22—C26—N2	178.3 (3)
C2—C3—C4—C5	−1.8 (5)	C23—C22—C26—C15	179.4 (3)
C3—C4—C5—O3	−179.6 (3)	C21—C22—C26—C15	−1.7 (4)
C3—C4—C5—C6	1.0 (5)	N1—C15—C26—N2	0.4 (4)
O3—C5—C6—C7	−179.1 (3)	C19—C15—C26—N2	−179.6 (2)
C4—C5—C6—C7	0.3 (5)	N1—C15—C26—C22	−179.6 (2)
C5—C6—C7—C2	−0.8 (5)	C19—C15—C26—C22	0.4 (4)
C3—C2—C7—C6	0.0 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3o···O2ⁱ	0.85	1.81	2.619 (3)	157
O6—H6o···O4ⁱⁱ	0.85	1.90	2.742 (3)	171
O1w—H1w1···O2wⁱⁱⁱ	0.85	2.01	2.819 (4)	158
O1w—H1w2···O5	0.85	1.84	2.599 (3)	148
O2w—H2w1···O5	0.85	2.04	2.801 (4)	148

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

Experimental details

Crystal data
Chemical formula	[Zn(C₇H₅O₃)₂(C₁₂H₈N₂)(H₂O)]·H₂O
M_r	555.83
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	11.1169 (5), 19.738 (1), 11.5503 (6)
β (°)	106.298 (1)
V (Å³)	2432.5 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.06
Crystal size (mm)	0.30 × 0.24 × 0.18

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.674, 0.832
No. of measured, independent and observed [I > 2σ(I)] reflections	23098, 5541, 3924
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.131, 1.08
No. of reflections	5541
No. of parameters	336
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.67, −0.88

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

Selected bond lengths (Å) top

Zn1—O1	2.025 (2)	Zn1—O1w	2.143 (2)
Zn1—O2	2.470 (2)	Zn1—N1	2.075 (2)
Zn1—O4	2.069 (2)	Zn1—N2	2.155 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3o···O2ⁱ	0.85	1.81	2.619 (3)	157
O6—H6o···O4ⁱⁱ	0.85	1.90	2.742 (3)	171
O1w—H1w1···O2wⁱⁱⁱ	0.85	2.01	2.819 (4)	158
O1w—H1w2···O5	0.85	1.84	2.599 (3)	148
O2w—H2w1···O5	0.85	2.04	2.801 (4)	148

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

Acknowledgements

We thank the Heilongjiang Province Natural Science Foundation (No. B200501), the Scientific Fund for Remarkable Teachers of Heilongjiang Province (No. 1054 G036), Heilongjiang University and the University of Malaya for supporting this work.

References

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