Bis(μ-cyclo­hexane-1,3-dicarboxyl­ato)-κ3O1:O4,O4′;κ3O1,O1′:O4-bis­[aqua­(1,10-phenanthroline-κ2N,N′)zinc(II)]

Rizal, M.R.; Ng, S.W.

doi:10.1107/S1600536809035144

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page m1178

doi:10.1107/S1600536809035144

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Bis(μ-cyclohexane-1,3-dicarboxylato)-κ³O¹:O⁴,O^4′;κ³O¹,O^1′:O⁴-bis[aqua(1,10-phenanthroline-κ²N,N′)zinc(II)]

Mohd. Razali Rizal ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 31 August 2009; accepted 1 September 2009; online 9 September 2009)

The cyclohexane-1,3-dicarboxylate dianion in the dinuclear centrosymmetric title compound, [Zn₂(C₈H₁₀O₄)₂(C₁₂H₈N₂)₂(H₂O)₂], has a chair conformation with both carboxylate groups in equatorial positions. One carboxylate group chelates a Zn^II atom, whereas the other binds through one O atom only to confer a six-coordinate status to the N-heterocycle-chelated water-coordinated Zn^II atom. Adjacent dinuclear molecules are linked by O—H⋯O hydrogen bonds into a linear chain.

Related literature

For the isostructural manganese(II) analog, see: Thirumurugan et al. (2006 ). For a review of the molecular architectures of metal carboxylate adducts of 2,2′-bipyridine-like ligands, see: Ye et al. (2003 ).

Experimental

Crystal data

[Zn₂(C₈H₁₀O₄)₂(C₁₂H₈N₂)₂(H₂O)₂]
M_r = 867.50
Monoclinic, P 2₁ /c
a = 9.6172 (2) Å
b = 17.4722 (5) Å
c = 11.4822 (3) Å
β = 104.393 (2)°
V = 1868.84 (8) Å³
Z = 2
Mo Kα radiation
μ = 1.35 mm⁻¹
T = 100 K
0.20 × 0.16 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.774, T_max = 0.823
9952 measured reflections
3289 independent reflections
2706 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.069
wR(F²) = 0.177
S = 1.09
3289 reflections
261 parameters
74 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.17 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1w—H11⋯O2	0.84 (6)	1.80 (7)	2.614 (6)	162 (8)
O1w—H12⋯O4ⁱ	0.84 (6)	1.89 (3)	2.701 (6)	161 (8)
Symmetry code: (i) x-1, y, 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: XSHELL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809035144/tk2534sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809035144/tk2534Isup2.hkl

checkCIF report

Related literature top

For the isostructural manganese(II) analog, see: Thirumurugan et al. (2006). For a review of the molecular architectures of metal carboxylate adducts of 2,2'-bipyridine-like ligands, see: Ye et al. (2003).

Experimental top

Zinc acetate (0.10 g, 0.46 mmol), cyclohexane-1,3-dicarboxylic acid (mixture of cis- and trans-isomers) (0.08 g, 0.46 mmol) and 1,10-phenanthroline (0.09 g, 0.46 mmol) along with water (18 ml) were heated in a 23-ml Teflon-lined stainless-steel Parr bomb. The bomb was heated at 403 K for 3 days. The bomb was cooled to room temperature at 5 K per hour. Tiny crystals were isolated from the solution.

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: XSHELL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

Fig. 1. 50% Probability displacement ellipsoid plot of Zn₂(H₂O)₂(C₁₂H₈N₂)₂(C₈H₁₀O₄)₂. Hydrogen atoms are drawn as spheres of arbitrary radius. Symmetry code (i): 2-x, 1-y, 1-z.

Bis(µ-cyclohexane-1,3-dicarboxylato)-κ³O¹: O⁴,O^4';κ³O¹,O^1':O⁴- bis[aqua(1,10-phenanthroline-κ²N,N')zinc(II)] top

Crystal data top

[Zn₂(C₈H₁₀O₄)₂(C₁₂H₈N₂)₂(H₂O)₂]	F(000) = 896
M_r = 867.50	D_x = 1.542 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2661 reflections
a = 9.6172 (2) Å	θ = 2.2–26.3°
b = 17.4722 (5) Å	µ = 1.35 mm⁻¹
c = 11.4822 (3) Å	T = 100 K
β = 104.393 (2)°	Block, colorless
V = 1868.84 (8) Å³	0.20 × 0.16 × 0.15 mm
Z = 2

Data collection top

Bruker SMART APEX diffractometer	3289 independent reflections
Radiation source: fine-focus sealed tube	2706 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.774, T_max = 0.823	k = −20→20
9952 measured reflections	l = −10→13

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.177	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.0653P)² + 9.3251P] where P = (F_o² + 2F_c²)/3
3289 reflections	(Δ/σ)_max = 0.001
261 parameters	Δρ_max = 1.17 e Å⁻³
74 restraints	Δρ_min = −0.51 e Å⁻³

Crystal data top

[Zn₂(C₈H₁₀O₄)₂(C₁₂H₈N₂)₂(H₂O)₂]	V = 1868.84 (8) Å³
M_r = 867.50	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.6172 (2) Å	µ = 1.35 mm⁻¹
b = 17.4722 (5) Å	T = 100 K
c = 11.4822 (3) Å	0.20 × 0.16 × 0.15 mm
β = 104.393 (2)°

Data collection top

Bruker SMART APEX diffractometer	3289 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2706 reflections with I > 2σ(I)
T_min = 0.774, T_max = 0.823	R_int = 0.032
9952 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.069	74 restraints
wR(F²) = 0.177	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 1.17 e Å⁻³
3289 reflections	Δρ_min = −0.51 e Å⁻³
261 parameters

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

	x	y	z	U_iso*/U_eq
Zn1	0.70076 (7)	0.51170 (4)	0.71412 (7)	0.0348 (3)
O1	0.8609 (5)	0.5855 (3)	0.7036 (5)	0.0516 (13)
O2	0.7359 (6)	0.6719 (3)	0.5775 (5)	0.0541 (14)
O3	1.1660 (5)	0.5852 (3)	0.3118 (4)	0.0461 (12)
O4	1.3286 (4)	0.5440 (3)	0.4667 (4)	0.0414 (11)
O1w	0.5440 (5)	0.5921 (3)	0.6510 (4)	0.0367 (10)
H11	0.593 (7)	0.626 (3)	0.627 (7)	0.06 (3)*
H12	0.471 (5)	0.572 (4)	0.606 (6)	0.05 (2)*
N1	0.5460 (6)	0.4333 (3)	0.7566 (5)	0.0394 (13)
N2	0.7539 (6)	0.5156 (4)	0.9034 (5)	0.0495 (16)
C1	1.1790 (11)	0.7240 (5)	0.4694 (11)	0.085 (3)
H1A	1.1088	0.7318	0.3912	0.102*
H1B	1.2750	0.7386	0.4598	0.102*
C2	1.1393 (10)	0.7760 (5)	0.5650 (11)	0.090 (4)
H2A	1.2152	0.7730	0.6410	0.108*
H2B	1.1322	0.8298	0.5371	0.108*
C3	0.9953 (11)	0.7504 (5)	0.5869 (12)	0.096 (4)
H3A	0.9754	0.7809	0.6536	0.116*
H3B	0.9179	0.7609	0.5139	0.116*
C4	0.9932 (9)	0.6721 (5)	0.6155 (10)	0.070 (3)
H4	1.0652	0.6653	0.6943	0.084*
C5	1.0389 (7)	0.6182 (4)	0.5277 (7)	0.0426 (16)
H5A	0.9630	0.6162	0.4516	0.051*
H5B	1.0517	0.5659	0.5620	0.051*
C6	1.1801 (9)	0.6455 (5)	0.5022 (9)	0.064 (2)
H6	1.2534	0.6415	0.5808	0.077*
C7	1.2268 (6)	0.5891 (4)	0.4205 (6)	0.0369 (15)
C8	0.8505 (7)	0.6411 (4)	0.6334 (8)	0.0499 (19)
C9	0.4467 (8)	0.3928 (4)	0.6845 (8)	0.0502 (18)
H9	0.4302	0.4013	0.6004	0.060*
C10	0.3633 (9)	0.3378 (5)	0.7238 (10)	0.066 (2)
H10	0.2932	0.3094	0.6675	0.079*
C11	0.3834 (10)	0.3256 (5)	0.8412 (11)	0.074 (3)
H11A	0.3270	0.2884	0.8689	0.089*
C12	0.4866 (10)	0.3671 (5)	0.9239 (8)	0.068 (3)
C13	0.5188 (13)	0.3622 (6)	1.0544 (11)	0.089 (3)
H13	0.4655	0.3274	1.0899	0.107*
C14	0.6173 (15)	0.4034 (7)	1.1242 (10)	0.094 (4)
H14	0.6321	0.3976	1.2086	0.113*
C15	0.7051 (12)	0.4574 (6)	1.0810 (8)	0.079 (3)
C16	0.8171 (14)	0.5024 (7)	1.1488 (10)	0.096 (4)
H16	0.8410	0.4975	1.2338	0.115*
C17	0.8914 (12)	0.5518 (7)	1.0997 (10)	0.092 (4)
H17	0.9654	0.5822	1.1484	0.110*
C18	0.8568 (8)	0.5576 (5)	0.9736 (7)	0.065 (2)
H18	0.9087	0.5927	0.9373	0.078*
C19	0.6786 (9)	0.4657 (5)	0.9548 (6)	0.053 (2)
C20	0.5701 (8)	0.4215 (4)	0.8787 (7)	0.0470 (18)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0269 (4)	0.0414 (4)	0.0374 (4)	−0.0027 (3)	0.0104 (3)	−0.0022 (3)
O1	0.031 (2)	0.049 (3)	0.076 (4)	−0.009 (2)	0.014 (2)	−0.004 (3)
O2	0.056 (3)	0.037 (3)	0.078 (4)	−0.011 (2)	0.033 (3)	−0.001 (2)
O3	0.032 (2)	0.060 (3)	0.044 (3)	0.002 (2)	0.004 (2)	0.001 (2)
O4	0.028 (2)	0.059 (3)	0.037 (3)	−0.005 (2)	0.0079 (19)	0.004 (2)
O1w	0.026 (2)	0.049 (3)	0.035 (3)	−0.002 (2)	0.008 (2)	0.002 (2)
N1	0.037 (3)	0.040 (3)	0.046 (3)	0.005 (2)	0.021 (3)	0.007 (3)
N2	0.040 (3)	0.067 (4)	0.034 (3)	0.026 (3)	−0.005 (3)	−0.017 (3)
C1	0.082 (6)	0.062 (6)	0.138 (10)	−0.014 (5)	0.079 (7)	−0.008 (6)
C2	0.080 (6)	0.057 (5)	0.164 (11)	−0.035 (5)	0.087 (7)	−0.049 (6)
C3	0.086 (7)	0.068 (6)	0.166 (11)	−0.039 (5)	0.090 (8)	−0.057 (7)
C4	0.057 (5)	0.051 (5)	0.120 (8)	−0.012 (4)	0.057 (5)	−0.016 (5)
C5	0.038 (4)	0.040 (4)	0.055 (5)	−0.008 (3)	0.019 (3)	−0.001 (3)
C6	0.055 (5)	0.056 (5)	0.098 (7)	−0.016 (4)	0.049 (5)	−0.025 (5)
C7	0.028 (3)	0.046 (4)	0.040 (4)	−0.011 (3)	0.015 (3)	−0.005 (3)
C8	0.036 (4)	0.047 (4)	0.075 (5)	−0.006 (3)	0.028 (4)	−0.022 (4)
C9	0.044 (4)	0.045 (4)	0.069 (5)	−0.008 (3)	0.028 (4)	−0.001 (3)
C10	0.054 (4)	0.049 (4)	0.109 (7)	−0.001 (3)	0.047 (5)	0.004 (4)
C11	0.065 (5)	0.050 (4)	0.126 (7)	0.019 (4)	0.059 (5)	0.028 (5)
C12	0.085 (5)	0.065 (5)	0.079 (5)	0.053 (4)	0.064 (5)	0.043 (4)
C13	0.107 (7)	0.086 (6)	0.100 (7)	0.064 (5)	0.073 (6)	0.056 (5)
C14	0.122 (7)	0.112 (7)	0.062 (6)	0.084 (6)	0.050 (6)	0.036 (5)
C15	0.091 (6)	0.090 (6)	0.055 (5)	0.067 (5)	0.020 (5)	0.009 (5)
C16	0.112 (7)	0.108 (7)	0.056 (5)	0.080 (6)	−0.003 (5)	−0.018 (5)
C17	0.077 (6)	0.102 (7)	0.071 (6)	0.055 (5)	−0.029 (5)	−0.044 (5)
C18	0.049 (4)	0.078 (5)	0.053 (4)	0.035 (4)	−0.015 (4)	−0.028 (4)
C19	0.062 (4)	0.067 (5)	0.035 (4)	0.046 (4)	0.019 (3)	0.012 (3)
C20	0.056 (4)	0.050 (4)	0.045 (4)	0.029 (3)	0.031 (3)	0.018 (3)

Geometric parameters (Å, º) top

Zn1—O1	2.035 (5)	C4—C5	1.521 (10)
Zn1—O3ⁱ	2.188 (5)	C4—C8	1.536 (9)
Zn1—O4ⁱ	2.247 (5)	C4—H4	1.0000
Zn1—O1w	2.056 (5)	C5—C6	1.536 (9)
Zn1—N1	2.166 (5)	C5—H5A	0.9900
Zn1—N2	2.107 (6)	C5—H5B	0.9900
O1—C8	1.250 (10)	C6—C7	1.504 (10)
O2—C8	1.251 (9)	C6—H6	1.0000
O3—C7	1.241 (8)	C9—C10	1.397 (10)
O3—Zn1ⁱ	2.188 (5)	C9—H9	0.9500
O4—C7	1.266 (8)	C10—C11	1.331 (14)
O4—Zn1ⁱ	2.247 (5)	C10—H10	0.9500
O1w—H11	0.84 (6)	C11—C12	1.394 (14)
O1w—H12	0.84 (6)	C11—H11A	0.9500
N1—C9	1.306 (9)	C12—C20	1.423 (11)
N1—C20	1.378 (9)	C12—C13	1.456 (15)
N2—C18	1.331 (10)	C13—C14	1.297 (16)
N2—C19	1.358 (11)	C13—H13	0.9500
C1—C6	1.422 (12)	C14—C15	1.434 (17)
C1—C2	1.544 (12)	C14—H14	0.9500
C1—H1A	0.9900	C15—C19	1.416 (11)
C1—H1B	0.9900	C15—C16	1.403 (16)
C2—C3	1.535 (10)	C16—C17	1.331 (17)
C2—H2A	0.9900	C16—H16	0.9500
C2—H2B	0.9900	C17—C18	1.407 (14)
C3—C4	1.408 (13)	C17—H17	0.9500
C3—H3A	0.9900	C18—H18	0.9500
C3—H3B	0.9900	C19—C20	1.412 (12)

O1—Zn1—O3ⁱ	90.3 (2)	C6—C5—H5A	109.6
O1—Zn1—O4ⁱ	98.2 (2)	C4—C5—H5B	109.6
O1—Zn1—O1w	92.6 (2)	C6—C5—H5B	109.6
O1—Zn1—N2	92.7 (2)	H5A—C5—H5B	108.1
O1—Zn1—N1	170.6 (2)	C1—C6—C7	116.8 (8)
O3ⁱ—Zn1—O4ⁱ	58.8 (2)	C1—C6—C5	113.7 (7)
O3ⁱ—Zn1—O1w	152.1 (2)	C7—C6—C5	109.3 (6)
O3ⁱ—Zn1—N1	90.0 (2)	C1—C6—H6	105.3
O3ⁱ—Zn1—N2	99.5 (2)	C7—C6—H6	105.3
O4ⁱ—Zn1—O1w	93.3 (2)	C5—C6—H6	105.3
O4ⁱ—Zn1—N1	89.9 (2)	O3—C7—O4	120.6 (6)
O4ⁱ—Zn1—N2	155.5 (2)	O3—C7—C6	121.6 (7)
O1w—Zn1—N1	91.6 (2)	O4—C7—C6	117.8 (7)
O1w—Zn1—N2	108.1 (2)	O2—C8—O1	125.7 (6)
N1—Zn1—N2	78.0 (2)	O2—C8—C4	118.9 (8)
C8—O1—Zn1	126.2 (5)	O1—C8—C4	115.4 (7)
C7—O3—Zn1ⁱ	91.9 (4)	N1—C9—C10	123.7 (8)
C7—O4—Zn1ⁱ	88.6 (4)	N1—C9—H9	118.1
Zn1—O1w—H11	100 (6)	C10—C9—H9	118.1
Zn1—O1w—H12	111 (5)	C11—C10—C9	119.2 (9)
H11—O1w—H12	123 (8)	C11—C10—H10	120.4
C9—N1—C20	118.4 (6)	C9—C10—H10	120.4
C9—N1—Zn1	129.4 (5)	C10—C11—C12	120.3 (8)
C20—N1—Zn1	111.9 (5)	C10—C11—H11A	119.8
C18—N2—C19	119.2 (7)	C12—C11—H11A	119.8
C18—N2—Zn1	126.6 (6)	C11—C12—C20	118.1 (8)
C19—N2—Zn1	114.1 (5)	C11—C12—C13	127.1 (9)
C6—C1—C2	111.5 (8)	C20—C12—C13	114.9 (10)
C6—C1—H1A	109.3	C14—C13—C12	122.6 (10)
C2—C1—H1A	109.3	C14—C13—H13	118.7
C6—C1—H1B	109.3	C12—C13—H13	118.7
C2—C1—H1B	109.3	C13—C14—C15	123.7 (10)
H1A—C1—H1B	108.0	C13—C14—H14	118.2
C3—C2—C1	109.7 (7)	C15—C14—H14	118.2
C3—C2—H2A	109.7	C14—C15—C19	116.7 (11)
C1—C2—H2A	109.7	C14—C15—C16	127.9 (11)
C3—C2—H2B	109.7	C19—C15—C16	115.4 (11)
C1—C2—H2B	109.7	C17—C16—C15	123.2 (10)
H2A—C2—H2B	108.2	C17—C16—H16	118.4
C4—C3—C2	112.8 (8)	C15—C16—H16	118.4
C4—C3—H3A	109.0	C16—C17—C18	117.9 (11)
C2—C3—H3A	109.0	C16—C17—H17	121.1
C4—C3—H3B	109.0	C18—C17—H17	121.1
C2—C3—H3B	109.0	N2—C18—C17	122.2 (11)
H3A—C3—H3B	107.8	N2—C18—H18	118.9
C3—C4—C5	115.1 (8)	C17—C18—H18	118.9
C3—C4—C8	116.0 (7)	N2—C19—C20	118.3 (6)
C5—C4—C8	106.6 (6)	N2—C19—C15	122.0 (9)
C3—C4—H4	106.1	C20—C19—C15	119.6 (9)
C5—C4—H4	106.1	N1—C20—C19	117.3 (6)
C8—C4—H4	106.1	N1—C20—C12	120.2 (8)
C4—C5—C6	110.4 (6)	C19—C20—C12	122.5 (8)
C4—C5—H5A	109.6

O1w—Zn1—O1—C8	−26.9 (6)	C3—C4—C8—O2	29.2 (13)
N2—Zn1—O1—C8	−135.2 (6)	C5—C4—C8—O2	−100.4 (8)
O3ⁱ—Zn1—O1—C8	125.3 (6)	C3—C4—C8—O1	−151.5 (9)
O4ⁱ—Zn1—O1—C8	66.8 (6)	C5—C4—C8—O1	78.9 (9)
O1w—Zn1—N1—C9	72.9 (6)	C20—N1—C9—C10	−0.2 (10)
N2—Zn1—N1—C9	−178.9 (6)	Zn1—N1—C9—C10	172.7 (5)
O3ⁱ—Zn1—N1—C9	−79.2 (6)	N1—C9—C10—C11	0.8 (12)
O4ⁱ—Zn1—N1—C9	−20.4 (6)	C9—C10—C11—C12	−0.2 (12)
O1w—Zn1—N1—C20	−113.8 (4)	C10—C11—C12—C20	−0.9 (11)
N2—Zn1—N1—C20	−5.6 (4)	C10—C11—C12—C13	178.2 (7)
O3ⁱ—Zn1—N1—C20	94.1 (4)	C11—C12—C13—C14	−180.0 (9)
O4ⁱ—Zn1—N1—C20	152.9 (4)	C20—C12—C13—C14	−0.9 (12)
O1—Zn1—N2—C18	2.1 (6)	C12—C13—C14—C15	−0.5 (14)
O1w—Zn1—N2—C18	−91.6 (5)	C13—C14—C15—C19	1.1 (13)
N1—Zn1—N2—C18	−179.3 (6)	C13—C14—C15—C16	−177.6 (9)
O3ⁱ—Zn1—N2—C18	92.8 (6)	C14—C15—C16—C17	−179.2 (9)
O4ⁱ—Zn1—N2—C18	118.8 (6)	C19—C15—C16—C17	2.2 (12)
O1—Zn1—N2—C19	−173.6 (4)	C15—C16—C17—C18	−1.2 (14)
O1w—Zn1—N2—C19	92.7 (5)	C19—N2—C18—C17	0.5 (10)
N1—Zn1—N2—C19	5.0 (4)	Zn1—N2—C18—C17	−175.0 (5)
O3ⁱ—Zn1—N2—C19	−82.9 (4)	C16—C17—C18—N2	−0.2 (12)
O4ⁱ—Zn1—N2—C19	−56.9 (7)	C18—N2—C19—C20	−179.8 (6)
C6—C1—C2—C3	−55.1 (14)	Zn1—N2—C19—C20	−3.8 (7)
C1—C2—C3—C4	53.5 (14)	C18—N2—C19—C15	0.6 (9)
C2—C3—C4—C5	−52.1 (13)	Zn1—N2—C19—C15	176.6 (5)
C2—C3—C4—C8	−177.5 (9)	C14—C15—C19—N2	179.3 (6)
C3—C4—C5—C6	48.8 (11)	C16—C15—C19—N2	−1.8 (10)
C8—C4—C5—C6	178.9 (8)	C14—C15—C19—C20	−0.2 (10)
C2—C1—C6—C7	−176.1 (8)	C16—C15—C19—C20	178.6 (6)
C2—C1—C6—C5	55.2 (12)	C9—N1—C20—C19	179.7 (6)
C4—C5—C6—C1	−50.4 (11)	Zn1—N1—C20—C19	5.5 (7)
C4—C5—C6—C7	177.0 (8)	C9—N1—C20—C12	−0.9 (9)
Zn1ⁱ—O3—C7—O4	1.5 (6)	Zn1—N1—C20—C12	−175.0 (5)
Zn1ⁱ—O3—C7—C6	−176.8 (5)	N2—C19—C20—N1	−1.3 (9)
Zn1ⁱ—O4—C7—O3	−1.4 (6)	C15—C19—C20—N1	178.3 (6)
Zn1ⁱ—O4—C7—C6	176.9 (5)	N2—C19—C20—C12	179.3 (6)
C1—C6—C7—O3	−56.5 (10)	C15—C19—C20—C12	−1.2 (10)
C5—C6—C7—O3	74.4 (9)	C11—C12—C20—N1	1.4 (9)
C1—C6—C7—O4	125.2 (9)	C13—C12—C20—N1	−177.7 (6)
C5—C6—C7—O4	−103.9 (8)	C11—C12—C20—C19	−179.1 (6)
Zn1—O1—C8—O2	17.5 (11)	C13—C12—C20—C19	1.7 (9)
Zn1—O1—C8—C4	−161.7 (5)

Symmetry code: (i) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H11···O2	0.84 (6)	1.80 (7)	2.614 (6)	162 (8)
O1w—H12···O4ⁱⁱ	0.84 (6)	1.89 (3)	2.701 (6)	161 (8)

Symmetry code: (ii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	[Zn₂(C₈H₁₀O₄)₂(C₁₂H₈N₂)₂(H₂O)₂]
M_r	867.50
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	9.6172 (2), 17.4722 (5), 11.4822 (3)
β (°)	104.393 (2)
V (Å³)	1868.84 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.35
Crystal size (mm)	0.20 × 0.16 × 0.15

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.774, 0.823
No. of measured, independent and observed [I > 2σ(I)] reflections	9952, 3289, 2706
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.177, 1.09
No. of reflections	3289
No. of parameters	261
No. of restraints	74
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.17, −0.51

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XSHELL (Sheldrick, 2008), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H11···O2	0.84 (6)	1.80 (7)	2.614 (6)	162 (8)
O1w—H12···O4ⁱ	0.84 (6)	1.89 (3)	2.701 (6)	161 (8)

Symmetry code: (i) x−1, y, z.

Acknowledgements

We thank the University of Malaya for supporting this study.

References

Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. 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
Thirumurugan, T., Avinash, M. B. & Rao, C. N. R. (2006). Dalton Trans. pp. 221–228. Web of Science CSD CrossRef Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar
Ye, B.-H., Tong, M.-L. & Chen, X.-M. (2003). Coord. Chem. Rev. 246, 185–202. Google Scholar

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