Di-μ2-acetato-1:2κ3O,O′:O;2:3κ3O:O,O′-tetra­kis(μ2-2-hydroxy­benzoato)-1:2κ4O:O′;2:3κ4O:O′-bis­(1,10-phenanthroline)-1κ2N,N′;3κ2N,N′-trizinc(II)

Cai, J.-H.; Xu, Y.-H.; Ng, S.W.

doi:10.1107/S1600536807054852

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Di-μ₂-acetato-1:2κ³O,O′:O;2:3κ³O:O,O′-tetrakis(μ₂-2-hydroxybenzoato)-1:2κ⁴O:O′;2:3κ⁴O:O′-bis(1,10-phenanthroline)-1κ²N,N′;3κ²N,N′-trizinc(II)

J.-H. Cai, Y.-H. Xu and S. W. Ng

The centrosymmetric trinuclear title compound, [Zn₃(C₂H₃O₂)₂(C₇H₅O₃)₄(C₁₂H₈N₂)₂], has six carboxylate groups each bridging two metal centers. The Zn atom on a center of inversion is coordinated by six O atoms in an octahedral environment. The other Zn atoms are each chelated by the N-heterocycle, and their coordination number is also six as the acetate group also functions as a chelating group. The hydroxy group of one of the two symmetry-independent salicylate groups is disordered over two positions in a 2:1 ratio.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807054852/bt2574sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807054852/bt2574Isup2.hkl Contains datablock I

CCDC reference: 672612

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
Disorder in main residue
R factor = 0.038
wR factor = 0.109
Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level B
ABSTM02_ALERT_3_B  The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
            Tmin and Tmax reported:      0.524     0.807
            Tmin(prime) and Tmax expected:      0.737     0.799
            RR(prime) =      0.704
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large .............       0.70
PLAT245_ALERT_2_B U(iso) H3      Smaller than U(eq) O3'     by ...       0.06 AngSq
PLAT420_ALERT_2_B D-H Without Acceptor       O6     -   H6O    ...          ?

Alert level C
PLAT150_ALERT_1_C Volume as Calculated Differs from that Given ...    2526.00 Ang-3
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       2.96 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O1
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O4
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O8
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C15
PLAT301_ALERT_3_C Main Residue  Disorder .........................       2.00 Perc.
PLAT313_ALERT_2_C Oxygen with three covalent bonds (rare) ........         O3
PLAT313_ALERT_2_C Oxygen with three covalent bonds (rare) ........        O3'
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C2     -   C7     ...       1.39 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C3     -   C4     ...       1.38 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  C6     ..  O3'     ..       3.01 Ang.

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          6

   0 ALERT level A = In general: serious problem
   4 ALERT level B = Potentially serious problem
  13 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  13 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The 2,2'-bipyridine adduct of zinc disalicylate exists in two form, a monomeric form (Lemoine et al., 2004) and a cyclotetrameric form (Wang et al., 2004). The attempt to synthesize the 1,10-phenanthroline analog gave the trinuclear compound in which part of the acetate entity that was present as the counterion is incorporated. The centrosymmetric trinuclear compound has six carboxylate groups each bridging two metal centers. The zinc atom on a center-of-inversion is coordinated to six oxygen atoms in an octahedral environment. The other zinc atoms are each chelated by the N-heterocycle, but their coordination number is six as the acetate group that is engaged in bridging also functions as a chelating group (Fig. 1).

Related literature top

For the structure of the diaquazinc derivative of salicylic acid, see Klug et al. (1958). The monomeric 2,2'-bipyridine adduct is reported by Lemoine et al. (2004) and the cyclic tetramer by Wang et al. (2004)

Experimental top

A solution of salicylic acid (1.0 mmol, 0.138 g) and sodium hydroxde (1.0 mmol, 0.040 g) in methanol (8 ml) was added to a solution of zinc acetate (1.0 mmol, 0.183 g) in methanol (8 ml). 1,10-Phenanthroline (1.0 mmol, 0.180 g), dissolved in methanol (5 ml), was then added. The mixture was placed in a 25-ml Teflon-lined stainless-steel Parr bomb. The bomb was heated at 363 K for five days. Colorless prismatic crystals were collected manually from the cool solution.

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2007).

Figures top

Fig. 1. Thermal displacement ellipsoid plot (50% probability) showing the numbering scheme. Hydrogen atoms are drawn as spheres of arbitrary radii; the minor disorder component is not shown.

Di-µ₂-acetato-1:2κ³O,O':O;2:3κ³O:O,O'-tetrakis(µ₂-2- hydroxybenzoato)-1:2κ⁴O:O';2:3κ⁴O:O'-bis(1,10-phenanthroline)- 1κ²N,N';3κ²N,N'-trizinc(II) top

Crystal data top

[Zn₃(C₂H₃O₂)₂(C₇H₅O₃)₄(C₁₂H₈N₂)₂]	F(000) = 1248
M_r = 1223.05	D_x = 1.608 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 873 reflections
a = 10.534 (3) Å	θ = 2.6–27.3°
b = 11.682 (3) Å	µ = 1.49 mm⁻¹
c = 20.533 (5) Å	T = 293 K
β = 91.847 (3)°	Prism, colorless
V = 2526 (1) Å³	0.20 × 0.16 × 0.15 mm
Z = 2

Data collection top

Bruker SMART diffractometer	5515 independent reflections
Radiation source: fine-focus sealed tube	4428 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ϕ and ω scans	θ_max = 27.1°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→13
T_min = 0.524, T_max = 0.807	k = −13→15
14442 measured reflections	l = −22→26

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H-atom parameters constrained
S = 0.87	w = 1/[σ²(F_o²) + (0.0711P)² + 2.1051P] where P = (F_o² + 2F_c²)/3
5515 reflections	(Δ/σ)_max = 0.001
369 parameters	Δρ_max = 0.65 e Å⁻³
6 restraints	Δρ_min = −0.66 e Å⁻³

Crystal data top

[Zn₃(C₂H₃O₂)₂(C₇H₅O₃)₄(C₁₂H₈N₂)₂]	V = 2526 (1) Å³
M_r = 1223.05	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.534 (3) Å	µ = 1.49 mm⁻¹
b = 11.682 (3) Å	T = 293 K
c = 20.533 (5) Å	0.20 × 0.16 × 0.15 mm
β = 91.847 (3)°

Data collection top

Bruker SMART diffractometer	5515 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4428 reflections with I > 2σ(I)
T_min = 0.524, T_max = 0.807	R_int = 0.027
14442 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	6 restraints
wR(F²) = 0.109	H-atom parameters constrained
S = 0.87	Δρ_max = 0.65 e Å⁻³
5515 reflections	Δρ_min = −0.66 e Å⁻³
369 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Zn1	0.5000	0.5000	0.5000	0.03664 (12)
Zn2	0.66125 (3)	0.24138 (2)	0.481223 (14)	0.03545 (10)
O1	0.4523 (2)	0.42396 (19)	0.41149 (10)	0.0558 (5)
O2	0.52731 (19)	0.24531 (17)	0.40656 (10)	0.0469 (5)
O3	0.4709 (3)	0.1262 (3)	0.30547 (17)	0.0597 (11)	0.678 (6)
H3O	0.5132	0.1318	0.3395	0.072*	0.678 (6)
O3'	0.3022 (7)	0.4892 (6)	0.3252 (4)	0.129 (6)	0.322 (6)
H3'	0.3424	0.4992	0.3596	0.155*	0.322 (6)
O4	0.4271 (2)	0.36795 (18)	0.55363 (12)	0.0564 (6)
O5	0.54382 (19)	0.20916 (17)	0.55701 (10)	0.0449 (5)
O6	0.2546 (3)	0.4024 (2)	0.63370 (17)	0.0939 (11)
H6O	0.1961	0.4394	0.6486	0.113*
O7	0.68027 (17)	0.41700 (17)	0.49590 (10)	0.0436 (4)
O8	0.8313 (2)	0.3264 (2)	0.54866 (12)	0.0654 (6)
N1	0.8123 (2)	0.23767 (18)	0.41080 (11)	0.0383 (5)
N2	0.7265 (2)	0.06882 (19)	0.48697 (11)	0.0387 (5)
C1	0.4616 (2)	0.3288 (2)	0.38461 (13)	0.0402 (6)
C2	0.3911 (2)	0.3120 (3)	0.32077 (13)	0.0410 (6)
C3	0.3126 (3)	0.3986 (3)	0.29541 (15)	0.0538 (8)
H3	0.3066	0.4674	0.3179	0.065*	0.322 (6)
C4	0.2437 (3)	0.3843 (4)	0.23748 (17)	0.0643 (9)
H4	0.1895	0.4418	0.2222	0.077*
C5	0.2556 (3)	0.2851 (4)	0.20281 (17)	0.0654 (10)
H5	0.2105	0.2759	0.1635	0.078*
C6	0.3336 (4)	0.1993 (4)	0.22567 (17)	0.0666 (10)
H6	0.3430	0.1331	0.2011	0.080*
C7	0.3996 (3)	0.2101 (3)	0.28591 (16)	0.0519 (7)
H7	0.4486	0.1499	0.3024	0.062*	0.678 (6)
C8	0.4555 (3)	0.2705 (2)	0.57659 (13)	0.0382 (6)
C9	0.3734 (3)	0.2265 (2)	0.62912 (13)	0.0415 (6)
C10	0.2767 (3)	0.2940 (3)	0.65424 (17)	0.0570 (8)
C11	0.1974 (4)	0.2487 (4)	0.7010 (2)	0.0700 (10)
H11	0.1336	0.2936	0.7180	0.084*
C12	0.2137 (4)	0.1386 (4)	0.72163 (18)	0.0705 (11)
H12	0.1600	0.1090	0.7525	0.085*
C13	0.3079 (4)	0.0706 (3)	0.69766 (17)	0.0648 (9)
H13	0.3177	−0.0046	0.7118	0.078*
C14	0.3882 (3)	0.1158 (3)	0.65202 (15)	0.0504 (7)
H14	0.4534	0.0708	0.6365	0.060*
C15	0.7842 (3)	0.4174 (3)	0.53085 (14)	0.0437 (6)
C16	0.8460 (3)	0.5300 (3)	0.5450 (2)	0.0737 (11)
H16A	0.9148	0.5196	0.5762	0.110*
H16B	0.7849	0.5818	0.5623	0.110*
H16C	0.8782	0.5612	0.5055	0.110*
C17	0.8725 (2)	0.1351 (2)	0.40841 (13)	0.0381 (6)
C18	0.8542 (3)	0.3217 (3)	0.37389 (15)	0.0494 (7)
H18	0.8133	0.3921	0.3750	0.059*
C19	0.9572 (3)	0.3090 (3)	0.33339 (16)	0.0584 (8)
H19	0.9847	0.3705	0.3088	0.070*
C20	1.0167 (3)	0.2069 (3)	0.33018 (17)	0.0587 (8)
H20	1.0847	0.1974	0.3029	0.070*
C21	0.9755 (3)	0.1147 (3)	0.36844 (15)	0.0468 (7)
C22	1.0342 (3)	0.0040 (3)	0.36999 (18)	0.0603 (9)
H22	1.1030	−0.0097	0.3438	0.072*
C23	0.9925 (3)	−0.0803 (3)	0.40818 (18)	0.0567 (8)
H23	1.0324	−0.1513	0.4078	0.068*
C24	0.8880 (3)	−0.0626 (2)	0.44929 (15)	0.0466 (7)
C25	0.8397 (3)	−0.1471 (3)	0.49062 (18)	0.0560 (8)
H25	0.8769	−0.2192	0.4925	0.067*
C26	0.7391 (3)	−0.1231 (3)	0.52754 (19)	0.0581 (8)
H26	0.7064	−0.1790	0.5546	0.070*
C27	0.6841 (3)	−0.0141 (3)	0.52503 (16)	0.0492 (7)
H27	0.6153	0.0010	0.5510	0.059*
C28	0.8269 (2)	0.0453 (2)	0.44954 (13)	0.0380 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0366 (2)	0.0344 (2)	0.0390 (2)	0.00356 (17)	0.00383 (17)	−0.00187 (16)
Zn2	0.03094 (17)	0.03523 (17)	0.04044 (18)	0.00558 (11)	0.00519 (12)	−0.00037 (12)
O1	0.0630 (14)	0.0581 (13)	0.0454 (11)	0.0113 (11)	−0.0103 (10)	−0.0113 (10)
O2	0.0380 (10)	0.0533 (12)	0.0489 (11)	0.0051 (9)	−0.0029 (9)	−0.0045 (9)
O3	0.070 (2)	0.0418 (18)	0.066 (2)	0.0129 (15)	−0.0090 (17)	−0.0103 (15)
O3'	0.197 (14)	0.058 (6)	0.126 (10)	0.027 (7)	−0.093 (9)	−0.004 (5)
O4	0.0528 (13)	0.0425 (11)	0.0755 (15)	0.0102 (9)	0.0252 (11)	0.0150 (10)
O5	0.0420 (11)	0.0445 (10)	0.0490 (11)	0.0098 (9)	0.0151 (9)	0.0066 (9)
O6	0.091 (2)	0.0586 (16)	0.136 (3)	0.0258 (15)	0.064 (2)	0.0017 (16)
O7	0.0328 (9)	0.0445 (10)	0.0535 (11)	0.0034 (8)	0.0017 (8)	−0.0069 (9)
O8	0.0687 (16)	0.0620 (15)	0.0647 (15)	0.0163 (12)	−0.0107 (12)	0.0029 (12)
N1	0.0340 (11)	0.0385 (11)	0.0425 (12)	0.0029 (9)	0.0054 (9)	−0.0004 (9)
N2	0.0295 (11)	0.0382 (11)	0.0485 (13)	0.0000 (9)	0.0031 (9)	−0.0008 (10)
C1	0.0317 (13)	0.0522 (16)	0.0368 (13)	−0.0007 (11)	0.0050 (10)	0.0010 (12)
C2	0.0333 (13)	0.0541 (16)	0.0360 (13)	−0.0066 (12)	0.0057 (11)	−0.0014 (12)
C3	0.0505 (18)	0.066 (2)	0.0440 (16)	−0.0023 (15)	−0.0028 (14)	0.0100 (15)
C4	0.0525 (19)	0.091 (3)	0.0493 (18)	−0.0137 (18)	−0.0038 (15)	0.0202 (18)
C5	0.052 (2)	0.099 (3)	0.0448 (17)	−0.023 (2)	0.0001 (15)	0.0067 (18)
C6	0.064 (2)	0.080 (2)	0.056 (2)	−0.021 (2)	0.0080 (17)	−0.0212 (18)
C7	0.0437 (16)	0.0589 (18)	0.0535 (18)	−0.0064 (14)	0.0071 (14)	−0.0056 (14)
C8	0.0337 (13)	0.0402 (14)	0.0409 (14)	0.0000 (11)	0.0046 (11)	−0.0002 (11)
C9	0.0377 (14)	0.0491 (15)	0.0379 (14)	−0.0026 (12)	0.0056 (11)	−0.0011 (11)
C10	0.0523 (19)	0.0594 (19)	0.0605 (19)	0.0004 (15)	0.0206 (15)	−0.0074 (16)
C11	0.057 (2)	0.088 (3)	0.067 (2)	−0.0026 (18)	0.0285 (18)	−0.0063 (19)
C12	0.059 (2)	0.102 (3)	0.051 (2)	−0.019 (2)	0.0160 (16)	0.0064 (19)
C13	0.064 (2)	0.073 (2)	0.058 (2)	−0.0118 (18)	0.0048 (17)	0.0216 (17)
C14	0.0454 (16)	0.0560 (18)	0.0499 (17)	0.0018 (14)	0.0045 (13)	0.0088 (14)
C15	0.0356 (14)	0.0475 (16)	0.0483 (16)	0.0001 (12)	0.0071 (12)	−0.0066 (12)
C16	0.051 (2)	0.066 (2)	0.105 (3)	−0.0151 (17)	0.009 (2)	−0.028 (2)
C17	0.0296 (12)	0.0433 (14)	0.0415 (14)	0.0036 (10)	0.0022 (10)	−0.0070 (11)
C18	0.0488 (17)	0.0483 (16)	0.0514 (17)	0.0019 (13)	0.0065 (13)	0.0045 (13)
C19	0.0503 (18)	0.069 (2)	0.0561 (19)	−0.0085 (16)	0.0112 (15)	0.0123 (16)
C20	0.0429 (17)	0.078 (2)	0.0565 (19)	0.0025 (16)	0.0166 (14)	−0.0009 (17)
C21	0.0332 (14)	0.0600 (18)	0.0475 (16)	0.0049 (12)	0.0073 (12)	−0.0122 (13)
C22	0.0428 (17)	0.070 (2)	0.069 (2)	0.0168 (15)	0.0123 (15)	−0.0173 (17)
C23	0.0453 (17)	0.0496 (17)	0.075 (2)	0.0146 (14)	0.0012 (15)	−0.0216 (16)
C24	0.0371 (14)	0.0393 (14)	0.0628 (18)	0.0056 (11)	−0.0061 (13)	−0.0117 (13)
C25	0.0543 (19)	0.0330 (14)	0.080 (2)	0.0044 (13)	−0.0091 (16)	−0.0025 (14)
C26	0.0549 (19)	0.0410 (16)	0.078 (2)	−0.0074 (14)	0.0013 (17)	0.0116 (15)
C27	0.0370 (15)	0.0475 (16)	0.0635 (19)	−0.0033 (12)	0.0082 (13)	0.0048 (14)
C28	0.0293 (12)	0.0387 (13)	0.0457 (14)	0.0031 (10)	−0.0012 (11)	−0.0063 (11)

Geometric parameters (Å, º) top

Zn1—O4	2.058 (2)	C6—H6	0.9300
Zn1—O4ⁱ	2.058 (2)	C7—H7	0.9300
Zn1—O1ⁱ	2.070 (2)	C8—C9	1.496 (4)
Zn1—O1	2.070 (2)	C9—C14	1.382 (4)
Zn1—O7ⁱ	2.1362 (19)	C9—C10	1.400 (4)
Zn1—O7	2.1362 (19)	C10—C11	1.396 (5)
Zn2—O2	2.050 (2)	C11—C12	1.363 (6)
Zn2—O5	2.0537 (19)	C11—H11	0.9300
Zn2—O7	2.082 (2)	C12—C13	1.375 (6)
Zn2—N2	2.132 (2)	C12—H12	0.9300
Zn2—N1	2.185 (2)	C13—C14	1.387 (4)
Zn2—O8	2.440 (3)	C13—H13	0.9300
O1—C1	1.246 (3)	C14—H14	0.9300
O2—C1	1.270 (3)	C15—C16	1.492 (4)
O3—C7	1.291 (4)	C16—H16A	0.9600
O3—H3O	0.8200	C16—H16B	0.9600
O3'—C3	1.228 (8)	C16—H16C	0.9600
O3'—H3'	0.8200	C17—C21	1.401 (4)
O4—C8	1.265 (3)	C17—C28	1.439 (4)
O5—C8	1.250 (3)	C18—C19	1.396 (4)
O6—C10	1.353 (4)	C18—H18	0.9300
O6—H6O	0.8200	C19—C20	1.350 (5)
O7—C15	1.290 (3)	C19—H19	0.9300
O8—C15	1.224 (4)	C20—C21	1.410 (5)
N1—C18	1.324 (4)	C20—H20	0.9300
N1—C17	1.357 (3)	C21—C22	1.433 (4)
N2—C27	1.331 (4)	C22—C23	1.342 (5)
N2—C28	1.356 (3)	C22—H22	0.9300
C1—C2	1.499 (4)	C23—C24	1.424 (4)
C2—C7	1.393 (4)	C23—H23	0.9300
C2—C3	1.397 (4)	C24—C25	1.407 (5)
C3—C4	1.384 (5)	C24—C28	1.415 (4)
C3—H3	0.9300	C25—C26	1.352 (5)
C4—C5	1.368 (6)	C25—H25	0.9300
C4—H4	0.9300	C26—C27	1.399 (4)
C5—C6	1.370 (6)	C26—H26	0.9300
C5—H5	0.9300	C27—H27	0.9300
C6—C7	1.405 (5)

O4—Zn1—O4ⁱ	180.00 (8)	C2—C7—C6	119.4 (3)
O4—Zn1—O1ⁱ	86.34 (10)	C2—C7—H7	120.3
O4ⁱ—Zn1—O1ⁱ	93.66 (10)	C6—C7—H7	120.3
O4—Zn1—O1	93.66 (10)	O5—C8—O4	124.4 (3)
O4ⁱ—Zn1—O1	86.34 (10)	O5—C8—C9	119.2 (2)
O1ⁱ—Zn1—O1	180.0	O4—C8—C9	116.3 (2)
O4—Zn1—O7ⁱ	88.39 (8)	C14—C9—C10	118.5 (3)
O4ⁱ—Zn1—O7ⁱ	91.61 (8)	C14—C9—C8	120.4 (3)
O1ⁱ—Zn1—O7ⁱ	87.79 (8)	C10—C9—C8	121.1 (3)
O1—Zn1—O7ⁱ	92.21 (8)	O6—C10—C11	118.0 (3)
O4—Zn1—O7	91.61 (8)	O6—C10—C9	122.2 (3)
O4ⁱ—Zn1—O7	88.39 (8)	C11—C10—C9	119.9 (3)
O1ⁱ—Zn1—O7	92.21 (8)	C12—C11—C10	120.0 (4)
O1—Zn1—O7	87.79 (8)	C12—C11—H11	120.0
O7ⁱ—Zn1—O7	180.0	C10—C11—H11	120.0
O2—Zn2—O5	98.85 (9)	C11—C12—C13	121.2 (3)
O2—Zn2—O7	98.44 (8)	C11—C12—H12	119.4
O5—Zn2—O7	97.38 (8)	C13—C12—H12	119.4
O2—Zn2—N2	105.98 (8)	C12—C13—C14	119.0 (4)
O5—Zn2—N2	89.18 (8)	C12—C13—H13	120.5
O7—Zn2—N2	153.43 (8)	C14—C13—H13	120.5
O2—Zn2—N1	90.23 (9)	C9—C14—C13	121.4 (3)
O5—Zn2—N1	165.29 (8)	C9—C14—H14	119.3
O7—Zn2—N1	92.67 (8)	C13—C14—H14	119.3
N2—Zn2—N1	77.15 (8)	O8—C15—O7	119.4 (3)
O2—Zn2—O8	152.90 (8)	O8—C15—C16	122.5 (3)
O5—Zn2—O8	95.38 (9)	O7—C15—C16	118.0 (3)
O7—Zn2—O8	56.72 (8)	C15—C16—H16A	109.5
N2—Zn2—O8	97.13 (8)	C15—C16—H16B	109.5
N1—Zn2—O8	81.17 (9)	H16A—C16—H16B	109.5
C1—O1—Zn1	138.7 (2)	C15—C16—H16C	109.5
C1—O2—Zn2	129.52 (18)	H16A—C16—H16C	109.5
C7—O3—H3O	120.0	H16B—C16—H16C	109.5
C3—O3'—H3'	120.0	N1—C17—C21	122.9 (3)
C8—O4—Zn1	141.86 (19)	N1—C17—C28	117.2 (2)
C8—O5—Zn2	127.65 (18)	C21—C17—C28	119.9 (3)
C10—O6—H6O	120.0	N1—C18—C19	122.8 (3)
C15—O7—Zn2	99.21 (17)	N1—C18—H18	118.6
C15—O7—Zn1	135.74 (18)	C19—C18—H18	118.6
Zn2—O7—Zn1	111.80 (9)	C20—C19—C18	119.6 (3)
C15—O8—Zn2	84.32 (18)	C20—C19—H19	120.2
C18—N1—C17	118.0 (2)	C18—C19—H19	120.2
C18—N1—Zn2	128.86 (19)	C19—C20—C21	119.7 (3)
C17—N1—Zn2	113.11 (17)	C19—C20—H20	120.1
C27—N2—C28	117.9 (2)	C21—C20—H20	120.1
C27—N2—Zn2	127.40 (19)	C17—C21—C20	117.0 (3)
C28—N2—Zn2	114.59 (17)	C17—C21—C22	118.8 (3)
O1—C1—O2	125.3 (3)	C20—C21—C22	124.1 (3)
O1—C1—C2	117.4 (3)	C23—C22—C21	121.7 (3)
O2—C1—C2	117.3 (2)	C23—C22—H22	119.1
C7—C2—C3	118.3 (3)	C21—C22—H22	119.1
C7—C2—C1	121.6 (3)	C22—C23—C24	120.9 (3)
C3—C2—C1	120.1 (3)	C22—C23—H23	119.6
O3'—C3—C4	118.6 (6)	C24—C23—H23	119.6
O3'—C3—C2	120.0 (5)	C25—C24—C28	116.7 (3)
C4—C3—C2	121.4 (3)	C25—C24—C23	123.8 (3)
C4—C3—H3	119.3	C28—C24—C23	119.5 (3)
C2—C3—H3	119.3	C26—C25—C24	119.9 (3)
C5—C4—C3	119.7 (4)	C26—C25—H25	120.1
C5—C4—H4	120.2	C24—C25—H25	120.1
C3—C4—H4	120.2	C25—C26—C27	119.9 (3)
C4—C5—C6	120.4 (3)	C25—C26—H26	120.0
C4—C5—H5	119.8	C27—C26—H26	120.0
C6—C5—H5	119.8	N2—C27—C26	122.5 (3)
C5—C6—C7	120.7 (4)	N2—C27—H27	118.7
C5—C6—H6	119.7	C26—C27—H27	118.7
C7—C6—H6	119.7	N2—C28—C24	123.1 (3)
O3—C7—C2	122.4 (3)	N2—C28—C17	117.8 (2)
O3—C7—C6	118.1 (3)	C24—C28—C17	119.1 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Zn₃(C₂H₃O₂)₂(C₇H₅O₃)₄(C₁₂H₈N₂)₂]
M_r	1223.05
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	10.534 (3), 11.682 (3), 20.533 (5)
β (°)	91.847 (3)
V (Å³)	2526 (1)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.49
Crystal size (mm)	0.20 × 0.16 × 0.15

Data collection
Diffractometer	Bruker SMART diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.524, 0.807
No. of measured, independent and observed [I > 2σ(I)] reflections	14442, 5515, 4428
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.642

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.109, 0.87
No. of reflections	5515
No. of parameters	369
No. of restraints	6
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.65, −0.66

Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), X-SEED (Barbour, 2001), publCIF (Westrip, 2007).

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