Bis(4-amino­benzoato)-κ2O,O′;κO-(2,2′-bipyridine-κ2N,N′)zinc

Huang, M.-L.; Wang, L.-L.

doi:10.1107/S1600536811039389

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page m1470

https://doi.org/10.1107/S1600536811039389

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Bis(4-aminobenzoato)-κ²O,O′;κO-(2,2′-bipyridine-κ²N,N′)zinc

Miao-Ling Huang ^a ^* and Ling-Ling Wang ^a

^aDepartment of Chemistry and Science of Life, Quanzhou Normal University, Fujian 362000, People's Republic of China
^*Correspondence e-mail: hml301@163.com

(Received 24 September 2011; accepted 26 September 2011; online 30 September 2011)

In the title complex, [Zn(C₇H₆NO₂)₂(C₁₀H₈N₂)], the Zn^II cation is coordinated by two aminobenzoate anions and one 2,2′-bipyridine ligand in a distorted trigonal–bipyramidal geometry. The carboxylate group of one aminobenzoate anion coordinates to the Zn^II cation in a monodentate manner, whereas the carboxylate group of the other aminobenzoate anion chelates the Zn cation with different Zn—O bond lengths. Intermolecular N—H⋯N and N—H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For applications of Zn complexes, see: Chohan & Naseer (2007 ); Huang et al. (2006 ); Ispir et al. (2006 ); Lo et al. (2007 ); Maria et al. (1996 ). For a related structure, see: Wang et al. (2005 ).

Experimental

Crystal data

[Zn(C₇H₆NO₂)₂(C₁₀H₈N₂)]
M_r = 493.81
Triclinic, $[P \overline 1]$
a = 7.9499 (14) Å
b = 10.7281 (19) Å
c = 13.905 (2) Å
α = 80.499 (2)°
β = 80.921 (2)°
γ = 70.538 (2)°
V = 1096.1 (3) Å³
Z = 2
Mo Kα radiation
μ = 1.16 mm⁻¹
T = 295 K
0.42 × 0.23 × 0.08 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.643, T_max = 0.914
8223 measured reflections
4058 independent reflections
3419 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.090
S = 1.07
4058 reflections
298 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Selected bond lengths (Å)

Zn1—O1	1.9269 (18)
Zn1—O3	1.9704 (18)
Zn1—O4	2.395 (2)
Zn1—N3	2.124 (2)
Zn1—N4	2.088 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1D⋯N2ⁱ	0.88	2.33	3.202 (4)	169
N1—H1E⋯O2ⁱⁱ	0.88	2.36	3.181 (4)	155
N2—H2E⋯O2ⁱⁱⁱ	0.88	2.28	3.116 (4)	159
Symmetry codes: (i) x-2, y+1, z; (ii) x-1, y, z; (iii) -x+1, -y, -z+1.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811039389/xu5334sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811039389/xu5334Isup2.hkl

checkCIF report

Comment top

In recent decades, zinc complexes have received much attention because of their interesting with biological ligands to generate stable mixed coordinated complexes, which play a key role in life process such as anti-cancer, antiseptic and anti-inflammatory (Ispir et al., 2006; Chohan & Naseer, 2007; Huang et al., 2006; Lo et al., 2007). 4-Aminobenzoic acid as an important part in the folic acid, which is a constituent of the vitamin B complex and is found in animal and plant tissues, has been shown to be a growth factor in certain microorganisms (Maria et al., 1996). In order to extend further the study of 4-aminobenzoic acid ligand coordinate to zinc ion, we synthesized the title complex and determined the crystal structure.

The asymmetric unit of 1 contains one zinc cation, two 4-aminobenzoic ion, and one 2,2'-bipyridine molecule. The Zn(II) atom is five-coordinated, forming a distorted trigonal-bipyramidal (Table 1). In the coordination polyhedron, the equatorial plane is occupied by two O(O1,O3) atoms from different 4-aba and one N(N4) atom from 2,2'-bipyridine, at the apex is situated one O(O4) atom from 4-aba and one N(N3) atom from 2,2'-bipyridine (Fig 1). The Zn(II) center is coordinated by two types of 4-aba: one behaves in an unsymmetrical chelating mode [Zn—O(3) 1.9704 (18) and Zn—O(4) 2.395 (2) Å]; the other acts as a monodentate ligand through one carboxylate oxygen atom [Zn—O(1) 1.9269 (18) and Zn—O(2) 2.841 Å], which is similar to previously reported complex {[Zn₂(4,4'-bipy)₂(4-aba)₄](H₂O)₅} (Wang et al., 2005). The dihedral angle between phenyl rings of the two 4-aba is 81.83 (7)°.

Hydrogen bonds are observed between the molecules in the crystal structure (Table 2).

Related literature top

For applications of Zn complexes, see: Chohan & Naseer (2007); Huang et al. (2006); Ispir et al. (2006); Lo et al. (2007); Maria et al. (1996). For a related structure, see: Wang et al. (2005).

Experimental top

An aqueous solution (5 ml) of ZnC₄H₆O₄.2H₂O (1 mmol) was added slowly to a mixed solution of 4-aminobenzoic acid (1.5 mmol) in H₂O (5 ml) and 2,2'-bipyridine (1 mmol) in ethanol (95%, 5 ml). After refluxing for 3 h, the mixture was filtered off while hot. The colourless single crystals suitable for X-ray analysis were obtained by slow evaporation of the above filtrate at room temperature after a month.

Structure description top

Hydrogen bonds are observed between the molecules in the crystal structure (Table 2).

For applications of Zn complexes, see: Chohan & Naseer (2007); Huang et al. (2006); Ispir et al. (2006); Lo et al. (2007); Maria et al. (1996). For a related structure, see: Wang et al. (2005).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The ORTEP drawing of the title compound (I). Displacement ellipsoids are drawn at 30% probability level.
	Fig. 2. Projection showing the two-dimensional structure formed by H-bonding interaction of the compound (I).

Bis(4-aminobenzoato)-κ²O,O';κO- (2,2'-bipyridine-κ²N,N')zinc top

Crystal data top

[Zn(C₇H₆NO₂)₂(C₁₀H₈N₂)]	Z = 2
M_r = 493.81	F(000) = 508
Triclinic, P1	D_x = 1.496 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9499 (14) Å	Cell parameters from 2868 reflections
b = 10.7281 (19) Å	θ = 2.4–24.9°
c = 13.905 (2) Å	µ = 1.16 mm⁻¹
α = 80.499 (2)°	T = 295 K
β = 80.921 (2)°	Block, colourless
γ = 70.538 (2)°	0.42 × 0.23 × 0.08 mm
V = 1096.1 (3) Å³

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	4058 independent reflections
Radiation source: fine-focus sealed tube	3419 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
φ and ω scans	θ_max = 25.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
T_min = 0.643, T_max = 0.914	k = −12→12
8223 measured reflections	l = −16→16

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.090	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0411P)² + 0.2825P] where P = (F_o² + 2F_c²)/3
4058 reflections	(Δ/σ)_max < 0.001
298 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

[Zn(C₇H₆NO₂)₂(C₁₀H₈N₂)]	γ = 70.538 (2)°
M_r = 493.81	V = 1096.1 (3) Å³
Triclinic, P1	Z = 2
a = 7.9499 (14) Å	Mo Kα radiation
b = 10.7281 (19) Å	µ = 1.16 mm⁻¹
c = 13.905 (2) Å	T = 295 K
α = 80.499 (2)°	0.42 × 0.23 × 0.08 mm
β = 80.921 (2)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	4058 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	3419 reflections with I > 2σ(I)
T_min = 0.643, T_max = 0.914	R_int = 0.024
8223 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.090	H-atom parameters constrained
S = 1.07	Δρ_max = 0.31 e Å⁻³
4058 reflections	Δρ_min = −0.31 e Å⁻³
298 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. 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
Zn1	0.14918 (4)	0.12380 (3)	0.19516 (2)	0.04021 (12)
O1	−0.1044 (2)	0.2151 (2)	0.21855 (14)	0.0528 (5)
O2	−0.0311 (3)	0.3661 (2)	0.27669 (18)	0.0732 (7)
O3	0.3785 (3)	0.10054 (19)	0.24420 (15)	0.0558 (5)
O4	0.2405 (3)	−0.0296 (2)	0.33755 (15)	0.0663 (6)
N1	−0.8907 (3)	0.5767 (3)	0.3483 (2)	0.0678 (7)
H1D	−0.9291	0.6259	0.3971	0.102*
H1E	−0.9611	0.5323	0.3389	0.102*
N2	1.0034 (4)	−0.2214 (3)	0.5101 (2)	0.0788 (9)
H2D	1.0548	−0.1604	0.5101	0.118*
H2E	0.9810	−0.2610	0.5693	0.118*
N3	0.2165 (3)	0.1976 (2)	0.04781 (16)	0.0502 (6)
N4	0.1805 (3)	−0.0382 (2)	0.12124 (15)	0.0419 (5)
C1	−0.3406 (3)	0.3914 (2)	0.28122 (17)	0.0362 (5)
C2	−0.4024 (4)	0.4919 (3)	0.3417 (2)	0.0488 (7)
H2	−0.3201	0.5185	0.3670	0.059*
C3	−0.5831 (4)	0.5529 (3)	0.3648 (2)	0.0537 (7)
H3	−0.6211	0.6196	0.4057	0.064*
C4	−0.7100 (3)	0.5157 (3)	0.3275 (2)	0.0444 (6)
C5	−0.6484 (3)	0.4166 (2)	0.26597 (19)	0.0417 (6)
H5	−0.7303	0.3914	0.2391	0.050*
C6	−0.4677 (3)	0.3554 (2)	0.24420 (18)	0.0375 (5)
H6	−0.4297	0.2882	0.2036	0.045*
C7	−0.1451 (3)	0.3227 (3)	0.25832 (18)	0.0423 (6)
C8	0.5359 (3)	−0.0506 (2)	0.36920 (17)	0.0368 (5)
C9	0.5508 (4)	−0.1572 (3)	0.44177 (19)	0.0479 (7)
H9	0.4560	−0.1919	0.4589	0.058*
C10	0.7028 (4)	−0.2133 (3)	0.4894 (2)	0.0560 (8)
H10	0.7105	−0.2861	0.5372	0.067*
C11	0.8444 (4)	−0.1614 (3)	0.4663 (2)	0.0495 (7)
C12	0.8290 (3)	−0.0533 (3)	0.3952 (2)	0.0474 (6)
H12	0.9222	−0.0167	0.3796	0.057*
C13	0.6791 (3)	0.0007 (3)	0.34731 (18)	0.0416 (6)
H13	0.6723	0.0730	0.2992	0.050*
C14	0.3746 (3)	0.0096 (3)	0.3162 (2)	0.0456 (6)
C15	0.2298 (5)	0.3190 (3)	0.0162 (3)	0.0771 (10)
H15	0.2011	0.3809	0.0607	0.093*
C16	0.2848 (7)	0.3549 (4)	−0.0801 (3)	0.1001 (14)
H16	0.2920	0.4402	−0.1006	0.120*
C17	0.3286 (6)	0.2642 (5)	−0.1448 (3)	0.0988 (14)
H17	0.3678	0.2865	−0.2100	0.119*
C18	0.3146 (5)	0.1395 (4)	−0.1135 (2)	0.0714 (9)
H18	0.3437	0.0765	−0.1571	0.086*
C19	0.2563 (3)	0.1089 (3)	−0.01574 (19)	0.0479 (7)
C20	0.2330 (3)	−0.0219 (3)	0.02410 (19)	0.0461 (6)
C21	0.2580 (5)	−0.1217 (3)	−0.0330 (2)	0.0702 (9)
H21	0.2929	−0.1097	−0.1000	0.084*
C22	0.2307 (6)	−0.2389 (4)	0.0103 (3)	0.0783 (10)
H22	0.2470	−0.3069	−0.0274	0.094*
C23	0.1794 (5)	−0.2557 (3)	0.1088 (2)	0.0673 (9)
H23	0.1607	−0.3348	0.1390	0.081*
C24	0.1561 (4)	−0.1535 (3)	0.1622 (2)	0.0534 (7)
H24	0.1221	−0.1648	0.2293	0.064*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.03267 (17)	0.04633 (19)	0.03920 (18)	−0.00652 (13)	−0.00538 (12)	−0.00961 (13)
O1	0.0335 (9)	0.0589 (12)	0.0619 (12)	−0.0044 (9)	−0.0064 (8)	−0.0168 (10)
O2	0.0385 (11)	0.0841 (16)	0.1075 (19)	−0.0255 (11)	−0.0096 (11)	−0.0263 (14)
O3	0.0480 (11)	0.0515 (12)	0.0688 (13)	−0.0078 (9)	−0.0261 (10)	−0.0074 (10)
O4	0.0385 (11)	0.1067 (18)	0.0642 (13)	−0.0291 (11)	−0.0019 (9)	−0.0299 (12)
N1	0.0407 (13)	0.0650 (17)	0.092 (2)	−0.0066 (12)	0.0100 (13)	−0.0317 (15)
N2	0.0660 (18)	0.0786 (19)	0.0765 (19)	0.0202 (15)	−0.0384 (15)	−0.0286 (15)
N3	0.0525 (14)	0.0509 (14)	0.0436 (13)	−0.0125 (11)	−0.0062 (11)	−0.0024 (11)
N4	0.0386 (11)	0.0477 (13)	0.0367 (12)	−0.0080 (10)	−0.0058 (9)	−0.0080 (10)
C1	0.0333 (12)	0.0379 (13)	0.0360 (13)	−0.0109 (10)	−0.0050 (10)	−0.0006 (11)
C2	0.0466 (16)	0.0530 (17)	0.0544 (17)	−0.0212 (13)	−0.0054 (13)	−0.0165 (13)
C3	0.0538 (17)	0.0496 (17)	0.0607 (18)	−0.0152 (14)	0.0040 (14)	−0.0272 (14)
C4	0.0370 (13)	0.0389 (14)	0.0521 (16)	−0.0087 (11)	0.0046 (12)	−0.0069 (12)
C5	0.0346 (13)	0.0412 (14)	0.0519 (15)	−0.0135 (11)	−0.0053 (11)	−0.0092 (12)
C6	0.0361 (13)	0.0355 (13)	0.0392 (13)	−0.0078 (10)	−0.0030 (10)	−0.0089 (11)
C7	0.0371 (14)	0.0484 (16)	0.0369 (14)	−0.0096 (12)	−0.0068 (11)	0.0012 (12)
C8	0.0330 (12)	0.0403 (14)	0.0373 (13)	−0.0090 (10)	−0.0007 (10)	−0.0133 (11)
C9	0.0513 (16)	0.0508 (16)	0.0463 (15)	−0.0246 (13)	0.0056 (13)	−0.0115 (13)
C10	0.074 (2)	0.0433 (16)	0.0413 (15)	−0.0070 (15)	−0.0095 (14)	0.0011 (12)
C11	0.0436 (15)	0.0522 (16)	0.0433 (15)	0.0072 (13)	−0.0117 (12)	−0.0200 (13)
C12	0.0339 (13)	0.0607 (18)	0.0493 (16)	−0.0137 (13)	−0.0017 (12)	−0.0166 (14)
C13	0.0380 (14)	0.0432 (14)	0.0421 (14)	−0.0116 (11)	−0.0056 (11)	−0.0025 (11)
C14	0.0349 (14)	0.0535 (17)	0.0504 (16)	−0.0071 (12)	−0.0044 (12)	−0.0270 (14)
C15	0.111 (3)	0.059 (2)	0.064 (2)	−0.034 (2)	−0.013 (2)	0.0027 (17)
C16	0.150 (4)	0.081 (3)	0.072 (3)	−0.056 (3)	−0.009 (3)	0.021 (2)
C17	0.128 (4)	0.107 (3)	0.055 (2)	−0.048 (3)	0.008 (2)	0.013 (2)
C18	0.083 (2)	0.077 (2)	0.0436 (17)	−0.0196 (19)	0.0055 (16)	−0.0039 (16)
C19	0.0380 (14)	0.0542 (17)	0.0414 (15)	−0.0035 (12)	−0.0025 (11)	−0.0029 (13)
C20	0.0405 (14)	0.0507 (16)	0.0413 (15)	−0.0034 (12)	−0.0083 (11)	−0.0093 (12)
C21	0.095 (3)	0.065 (2)	0.0431 (17)	−0.0107 (19)	−0.0063 (17)	−0.0166 (15)
C22	0.114 (3)	0.058 (2)	0.063 (2)	−0.017 (2)	−0.016 (2)	−0.0232 (17)
C23	0.090 (2)	0.0486 (18)	0.066 (2)	−0.0206 (17)	−0.0171 (18)	−0.0092 (16)
C24	0.0610 (18)	0.0525 (17)	0.0464 (16)	−0.0170 (14)	−0.0079 (13)	−0.0054 (13)

Geometric parameters (Å, º) top

Zn1—O1	1.9269 (18)	C6—H6	0.9300
Zn1—O3	1.9704 (18)	C8—C9	1.381 (4)
Zn1—O4	2.395 (2)	C8—C13	1.394 (3)
Zn1—N3	2.124 (2)	C8—C14	1.481 (4)
Zn1—N4	2.088 (2)	C9—C10	1.377 (4)
Zn1—C14	2.521 (3)	C9—H9	0.9300
O1—C7	1.284 (3)	C10—C11	1.387 (4)
O2—C7	1.223 (3)	C10—H10	0.9300
O3—C14	1.282 (3)	C11—C12	1.380 (4)
O4—C14	1.249 (3)	C12—C13	1.364 (3)
N1—C4	1.372 (3)	C12—H12	0.9300
N1—H1D	0.8818	C13—H13	0.9300
N1—H1E	0.8820	C15—C16	1.375 (5)
N2—C11	1.397 (3)	C15—H15	0.9300
N2—H2D	0.8798	C16—C17	1.358 (6)
N2—H2E	0.8825	C16—H16	0.9300
N3—C19	1.332 (4)	C17—C18	1.372 (5)
N3—C15	1.338 (4)	C17—H17	0.9300
N4—C24	1.335 (3)	C18—C19	1.388 (4)
N4—C20	1.350 (3)	C18—H18	0.9300
C1—C2	1.388 (4)	C19—C20	1.481 (4)
C1—C6	1.388 (3)	C20—C21	1.381 (4)
C1—C7	1.490 (3)	C21—C22	1.371 (5)
C2—C3	1.375 (4)	C21—H21	0.9300
C2—H2	0.9300	C22—C23	1.367 (5)
C3—C4	1.396 (4)	C22—H22	0.9300
C3—H3	0.9300	C23—C24	1.371 (4)
C4—C5	1.386 (4)	C23—H23	0.9300
C5—C6	1.373 (3)	C24—H24	0.9300
C5—H5	0.9300

O1—Zn1—O3	141.27 (9)	C13—C8—C14	120.3 (2)
O1—Zn1—N4	107.51 (8)	C10—C9—C8	121.5 (3)
O3—Zn1—N4	108.58 (8)	C10—C9—H9	119.2
O1—Zn1—N3	103.23 (9)	C8—C9—H9	119.2
O3—Zn1—N3	97.43 (9)	C9—C10—C11	120.2 (3)
N4—Zn1—N3	78.22 (9)	C9—C10—H10	119.9
O1—Zn1—O4	108.31 (8)	C11—C10—H10	119.9
O3—Zn1—O4	59.37 (8)	C12—C11—C10	118.6 (2)
N4—Zn1—O4	88.61 (8)	C12—C11—N2	120.4 (3)
N3—Zn1—O4	148.23 (8)	C10—C11—N2	120.9 (3)
O1—Zn1—C14	129.59 (8)	C13—C12—C11	121.0 (3)
O3—Zn1—C14	30.11 (8)	C13—C12—H12	119.5
N4—Zn1—C14	98.66 (8)	C11—C12—H12	119.5
N3—Zn1—C14	124.19 (9)	C12—C13—C8	121.2 (2)
O4—Zn1—C14	29.29 (8)	C12—C13—H13	119.4
C7—O1—Zn1	114.85 (16)	C8—C13—H13	119.4
C14—O3—Zn1	99.43 (16)	O4—C14—O3	120.2 (3)
C14—O4—Zn1	80.92 (18)	O4—C14—C8	121.8 (3)
C4—N1—H1D	119.3	O3—C14—C8	118.0 (2)
C4—N1—H1E	115.8	O4—C14—Zn1	69.79 (16)
H1D—N1—H1E	115.8	O3—C14—Zn1	50.46 (12)
C11—N2—H2D	108.4	C8—C14—Zn1	167.2 (2)
C11—N2—H2E	110.2	N3—C15—C16	121.9 (4)
H2D—N2—H2E	113.1	N3—C15—H15	119.1
C19—N3—C15	119.3 (3)	C16—C15—H15	119.1
C19—N3—Zn1	114.43 (18)	C17—C16—C15	119.1 (4)
C15—N3—Zn1	126.2 (2)	C17—C16—H16	120.5
C24—N4—C20	119.2 (2)	C15—C16—H16	120.5
C24—N4—Zn1	125.67 (18)	C16—C17—C18	119.6 (3)
C20—N4—Zn1	115.14 (18)	C16—C17—H17	120.2
C2—C1—C6	117.6 (2)	C18—C17—H17	120.2
C2—C1—C7	121.3 (2)	C17—C18—C19	118.9 (3)
C6—C1—C7	121.1 (2)	C17—C18—H18	120.5
C3—C2—C1	121.3 (2)	C19—C18—H18	120.5
C3—C2—H2	119.4	N3—C19—C18	121.2 (3)
C1—C2—H2	119.4	N3—C19—C20	116.1 (2)
C2—C3—C4	120.8 (2)	C18—C19—C20	122.7 (3)
C2—C3—H3	119.6	N4—C20—C21	120.7 (3)
C4—C3—H3	119.6	N4—C20—C19	115.9 (2)
N1—C4—C5	120.3 (3)	C21—C20—C19	123.4 (3)
N1—C4—C3	121.7 (3)	C22—C21—C20	119.3 (3)
C5—C4—C3	118.0 (2)	C22—C21—H21	120.4
C6—C5—C4	120.8 (2)	C20—C21—H21	120.4
C6—C5—H5	119.6	C23—C22—C21	119.9 (3)
C4—C5—H5	119.6	C23—C22—H22	120.0
C5—C6—C1	121.6 (2)	C21—C22—H22	120.0
C5—C6—H6	119.2	C22—C23—C24	118.5 (3)
C1—C6—H6	119.2	C22—C23—H23	120.7
O2—C7—O1	122.4 (2)	C24—C23—H23	120.7
O2—C7—C1	122.0 (3)	N4—C24—C23	122.4 (3)
O1—C7—C1	115.6 (2)	N4—C24—H24	118.8
C9—C8—C13	117.5 (2)	C23—C24—H24	118.8
C9—C8—C14	122.2 (2)

O3—Zn1—O1—C7	26.2 (3)	C10—C11—C12—C13	−0.9 (4)
N4—Zn1—O1—C7	−175.82 (17)	N2—C11—C12—C13	175.6 (2)
N3—Zn1—O1—C7	−94.20 (19)	C11—C12—C13—C8	0.6 (4)
O4—Zn1—O1—C7	89.73 (19)	C9—C8—C13—C12	0.6 (4)
C14—Zn1—O1—C7	66.4 (2)	C14—C8—C13—C12	−179.9 (2)
O1—Zn1—O3—C14	83.1 (2)	Zn1—O4—C14—O3	3.2 (2)
N4—Zn1—O3—C14	−74.76 (17)	Zn1—O4—C14—C8	−173.9 (2)
N3—Zn1—O3—C14	−154.77 (16)	Zn1—O3—C14—O4	−3.9 (3)
O4—Zn1—O3—C14	2.02 (14)	Zn1—O3—C14—C8	173.36 (18)
O1—Zn1—O4—C14	−141.45 (15)	C9—C8—C14—O4	3.2 (4)
O3—Zn1—O4—C14	−2.07 (15)	C13—C8—C14—O4	−176.3 (2)
N4—Zn1—O4—C14	110.56 (16)	C9—C8—C14—O3	−174.0 (2)
N3—Zn1—O4—C14	45.8 (2)	C13—C8—C14—O3	6.5 (3)
O1—Zn1—N3—C19	−109.74 (19)	C9—C8—C14—Zn1	−150.2 (7)
O3—Zn1—N3—C19	103.24 (19)	C13—C8—C14—Zn1	30.3 (9)
N4—Zn1—N3—C19	−4.28 (19)	O1—Zn1—C14—O4	50.15 (19)
O4—Zn1—N3—C19	63.2 (3)	O3—Zn1—C14—O4	176.4 (3)
C14—Zn1—N3—C19	88.3 (2)	N4—Zn1—C14—O4	−71.23 (16)
O1—Zn1—N3—C15	73.6 (3)	N3—Zn1—C14—O4	−152.83 (15)
O3—Zn1—N3—C15	−73.4 (3)	O1—Zn1—C14—O3	−126.29 (17)
N4—Zn1—N3—C15	179.1 (3)	N4—Zn1—C14—O3	112.32 (16)
O4—Zn1—N3—C15	−113.5 (3)	N3—Zn1—C14—O3	30.7 (2)
C14—Zn1—N3—C15	−88.4 (3)	O4—Zn1—C14—O3	−176.4 (3)
O1—Zn1—N4—C24	−77.9 (2)	O1—Zn1—C14—C8	−153.8 (8)
O3—Zn1—N4—C24	87.8 (2)	O3—Zn1—C14—C8	−27.5 (8)
N3—Zn1—N4—C24	−178.2 (2)	N4—Zn1—C14—C8	84.8 (8)
O4—Zn1—N4—C24	30.9 (2)	N3—Zn1—C14—C8	3.2 (9)
C14—Zn1—N4—C24	58.5 (2)	O4—Zn1—C14—C8	156.1 (9)
O1—Zn1—N4—C20	103.27 (18)	C19—N3—C15—C16	−0.5 (5)
O3—Zn1—N4—C20	−91.02 (18)	Zn1—N3—C15—C16	176.0 (3)
N3—Zn1—N4—C20	2.95 (17)	N3—C15—C16—C17	−0.7 (7)
O4—Zn1—N4—C20	−147.95 (18)	C15—C16—C17—C18	1.0 (7)
C14—Zn1—N4—C20	−120.34 (18)	C16—C17—C18—C19	−0.2 (6)
C6—C1—C2—C3	0.6 (4)	C15—N3—C19—C18	1.3 (4)
C7—C1—C2—C3	−178.3 (2)	Zn1—N3—C19—C18	−175.6 (2)
C1—C2—C3—C4	−0.3 (4)	C15—N3—C19—C20	−178.2 (3)
C2—C3—C4—N1	−178.9 (3)	Zn1—N3—C19—C20	4.9 (3)
C2—C3—C4—C5	−0.6 (4)	C17—C18—C19—N3	−0.9 (5)
N1—C4—C5—C6	179.6 (2)	C17—C18—C19—C20	178.5 (3)
C3—C4—C5—C6	1.3 (4)	C24—N4—C20—C21	1.3 (4)
C4—C5—C6—C1	−1.1 (4)	Zn1—N4—C20—C21	−179.8 (2)
C2—C1—C6—C5	0.1 (4)	C24—N4—C20—C19	179.7 (2)
C7—C1—C6—C5	179.0 (2)	Zn1—N4—C20—C19	−1.4 (3)
Zn1—O1—C7—O2	2.4 (3)	N3—C19—C20—N4	−2.4 (3)
Zn1—O1—C7—C1	−177.28 (15)	C18—C19—C20—N4	178.1 (3)
C2—C1—C7—O2	−13.1 (4)	N3—C19—C20—C21	176.0 (3)
C6—C1—C7—O2	168.1 (3)	C18—C19—C20—C21	−3.5 (4)
C2—C1—C7—O1	166.6 (2)	N4—C20—C21—C22	−0.7 (5)
C6—C1—C7—O1	−12.2 (3)	C19—C20—C21—C22	−179.0 (3)
C13—C8—C9—C10	−1.5 (4)	C20—C21—C22—C23	0.0 (6)
C14—C8—C9—C10	179.0 (2)	C21—C22—C23—C24	0.1 (6)
C8—C9—C10—C11	1.2 (4)	C20—N4—C24—C23	−1.2 (4)
C9—C10—C11—C12	0.0 (4)	Zn1—N4—C24—C23	−180.0 (2)
C9—C10—C11—N2	−176.5 (2)	C22—C23—C24—N4	0.5 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1D···N2ⁱ	0.88	2.33	3.202 (4)	169
N1—H1E···O2ⁱⁱ	0.88	2.36	3.181 (4)	155
N2—H2E···O2ⁱⁱⁱ	0.88	2.28	3.116 (4)	159

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

Experimental details

Crystal data
Chemical formula	[Zn(C₇H₆NO₂)₂(C₁₀H₈N₂)]
M_r	493.81
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	7.9499 (14), 10.7281 (19), 13.905 (2)
α, β, γ (°)	80.499 (2), 80.921 (2), 70.538 (2)
V (Å³)	1096.1 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.16
Crystal size (mm)	0.42 × 0.23 × 0.08

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.643, 0.914
No. of measured, independent and observed [I > 2σ(I)] reflections	8223, 4058, 3419
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.090, 1.07
No. of reflections	4058
No. of parameters	298
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.31

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Zn1—O1	1.9269 (18)	Zn1—N3	2.124 (2)
Zn1—O3	1.9704 (18)	Zn1—N4	2.088 (2)
Zn1—O4	2.395 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1D···N2ⁱ	0.88	2.33	3.202 (4)	169.3
N1—H1E···O2ⁱⁱ	0.88	2.36	3.181 (4)	155.3
N2—H2E···O2ⁱⁱⁱ	0.88	2.28	3.116 (4)	158.5

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

Acknowledgements

This work was supported by the Education Department Foundation of Fujian Province of China (grant No. JK2011042).

References

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