(2,2′-Bipyridine-κ2N,N′)bis­(4-methyl­benzoato-κ2O,O′)zinc(II)

Shao, Y.-Q.

doi:10.1107/S1600536808009483

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page m655

doi:10.1107/S1600536808009483

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(2,2′-Bipyridine-κ²N,N′)bis(4-methylbenzoato-κ²O,O′)zinc(II)

Yan-Qiu Shao ^a ^*

^aDepartment of Chemistry, Mudanjiang Normal College, Mudanjiang 157012, People's Republic of China
^*Correspondence e-mail: shaoyq60@yahoo.cn

(Received 19 March 2008; accepted 7 April 2008; online 10 April 2008)

In the title compound, [Zn(C₈H₇O₂)₂(C₁₀H₈N₂)], the Zn^II atom is coordinated by four O atoms from two chelating 4-methylbenzoate ligands and two N atoms from a 2,2′-bipyridine ligand, displaying a disordered octahedral geometry. C—H⋯O hydrogen bonds connect the complex molecules into a three-dimensional supramolecular structure.

Related literature

For related literature, see: Choi & Jeon (2003 ); Guilera & Steed (1999 ); Tao et al. (2000 ).

Experimental

Crystal data

[Zn(C₈H₇O₂)₂(C₁₀H₈N₂)]
M_r = 491.83
Triclinic, $[P \overline 1]$
a = 7.6172 (3) Å
b = 9.8211 (4) Å
c = 15.7595 (6) Å
α = 79.130 (2)°
β = 83.977 (2)°
γ = 79.958 (2)°
V = 1136.90 (8) Å³
Z = 2
Mo Kα radiation
μ = 1.12 mm⁻¹
T = 296 (2) K
0.26 × 0.23 × 0.21 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.760, T_max = 0.799
10295 measured reflections
4047 independent reflections
3281 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.087
S = 1.02
4047 reflections
300 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

N1—Zn1	2.090 (2)
N2—Zn1	2.103 (2)
O1—Zn1	2.509 (2)
O2—Zn1	1.9852 (18)
O3—Zn1	2.0626 (17)
O4—Zn1	2.2058 (19)

O1—Zn1—O2	57.03 (7)
O1—Zn1—O3	95.86 (7)
O1—Zn1—O4	103.13 (7)
O1—Zn1—N1	92.92 (7)
O1—Zn1—N2	155.41 (8)
O2—Zn1—O3	145.10 (8)
O2—Zn1—N1	105.58 (8)
O3—Zn1—N1	96.58 (8)
O2—Zn1—N2	103.12 (8)
O3—Zn1—N2	107.73 (8)
N1—Zn1—N2	77.88 (9)
O2—Zn1—O4	100.93 (7)
O3—Zn1—O4	61.19 (7)
N1—Zn1—O4	153.43 (8)
N2—Zn1—O4	94.46 (8)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O3ⁱ	0.93	2.53	3.293 (3)	139
C4—H4⋯O1ⁱ	0.93	2.48	3.385 (3)	165
C14—H14⋯O4ⁱⁱ	0.93	2.51	3.417 (3)	164
C15—H15⋯O2ⁱⁱ	0.93	2.57	3.395 (3)	148
C20—H20⋯O3ⁱⁱⁱ	0.93	2.43	3.189 (4)	139
C23—H23⋯O2^iv	0.93	2.56	3.230 (4)	129
Symmetry codes: (i) x-1, y, z; (ii) x+1, y, z; (iii) -x+1, -y+1, -z; (iv) -x, -y+1, -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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808009483/hy2125sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808009483/hy2125Isup2.hkl

checkCIF report

Comment top

Molecular self-assembly of supramolecular architectures has received much attention during recent decades (Tao et al., 2000; Choi & Jeon, 2003). The structures and properties of such systems depend on the coordination and geometric preferences of both the central metal ions and the bridging building blocks, as well as on the influence of weaker non-covalent interactions, such as hydrogen bonds and π–π stacking interactions. As a building block, 4-methylbenzoate is an excellent candidate for the construction of supramolecular complexes. Recently, we obtained the title mononuclear complex by the reaction of cadmium chloride with 4-methylbenzoic acid and 2,2'-bipyridine in an aqueous solution and its crystal structure is reported here.

As depicted in Fig. 1, the Zn^II atom is coordinated by four O atoms from two 4-methylbenzoate ligands and two N atoms from one 2,2'-bipyridine ligand. The 4-methylbenzoates act as bidentate chelating ligands. The Zn1—O1 distance of 2.509 (2) Å (Table 1) suggests a non-negligible interaction, or a chelating coordination mode (Guilera & Steed, 1999). The complex molecules are connected by C—H···O hydrogen bonds (Table 2), resulting in a three-dimensional supramolecular network.

Related literature top

For related literature, see: Choi & Jeon (2003); Guilera & Steed (1999); Tao et al. (2000).

Experimental top

The title compound was prepared by the addition of a stoichiometric amount of cadmium chloride (0.228 g, 1 mmol) and 2,2'-bipyridine (0.156 g, 1 mmol) to a hot aqueous solution (25 ml) of 4-methylbenzoic acid (2.72 g, 20 mmol). The pH value was then adjusted to 7.0 to 8.0 with NaOH (1 mmol). The resulting solution was filtered, and colorless single crystals were obtained at room temperature over several days.

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level.

(2,2'-Bipyridine-κ²N,N')bis(4-methylbenzoato- κ²O,O')zinc(II) top

Crystal data top

[Zn(C₈H₇O₂)₂(C₁₀H₈N₂)]	Z = 2
M_r = 491.83	F(000) = 508
Triclinic, P1	D_x = 1.437 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.6172 (3) Å	Cell parameters from 3500 reflections
b = 9.8211 (4) Å	θ = 1.3–28.0°
c = 15.7595 (6) Å	µ = 1.12 mm⁻¹
α = 79.130 (2)°	T = 296 K
β = 83.977 (2)°	Block, colorless
γ = 79.958 (2)°	0.26 × 0.23 × 0.21 mm
V = 1136.90 (8) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4047 independent reflections
Radiation source: fine-focus sealed tube	3281 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ϕ and ω scans	θ_max = 25.2°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
T_min = 0.760, T_max = 0.800	k = −11→11
10295 measured reflections	l = −18→18

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) = 0.087	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0378P)² + 0.345P] where P = (F_o² + 2F_c²)/3
4047 reflections	(Δ/σ)_max = 0.001
300 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

[Zn(C₈H₇O₂)₂(C₁₀H₈N₂)]	γ = 79.958 (2)°
M_r = 491.83	V = 1136.90 (8) Å³
Triclinic, P1	Z = 2
a = 7.6172 (3) Å	Mo Kα radiation
b = 9.8211 (4) Å	µ = 1.12 mm⁻¹
c = 15.7595 (6) Å	T = 296 K
α = 79.130 (2)°	0.26 × 0.23 × 0.21 mm
β = 83.977 (2)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4047 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	3281 reflections with I > 2σ(I)
T_min = 0.760, T_max = 0.800	R_int = 0.030
10295 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.087	H-atom parameters constrained
S = 1.02	Δρ_max = 0.22 e Å⁻³
4047 reflections	Δρ_min = −0.29 e Å⁻³
300 parameters

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

	x	y	z	U_iso*/U_eq
C1	−0.0510 (3)	0.7966 (3)	0.21798 (15)	0.0470 (6)
C2	−0.2171 (3)	0.8766 (2)	0.25555 (15)	0.0411 (6)
C3	−0.3837 (3)	0.8465 (3)	0.24538 (16)	0.0453 (6)
H3	−0.3925	0.7784	0.2130	0.054*
C4	−0.5367 (3)	0.9160 (3)	0.28257 (17)	0.0487 (6)
H4	−0.6476	0.8966	0.2731	0.058*
C5	−0.5282 (4)	1.0141 (3)	0.33374 (17)	0.0497 (6)
C6	−0.3604 (4)	1.0445 (3)	0.34364 (17)	0.0531 (7)
H6	−0.3512	1.1105	0.3775	0.064*
C7	−0.2073 (4)	0.9783 (3)	0.30400 (16)	0.0486 (6)
H7	−0.0970	1.0023	0.3099	0.058*
C8	−0.6941 (4)	1.0840 (3)	0.3795 (2)	0.0725 (9)
H8A	−0.7971	1.0515	0.3650	0.109*
H8B	−0.7059	1.1839	0.3614	0.109*
H8C	−0.6848	1.0610	0.4409	0.109*
C9	0.3993 (3)	0.4970 (3)	0.29191 (16)	0.0446 (6)
C10	0.5328 (3)	0.4398 (2)	0.35701 (15)	0.0404 (6)
C11	0.4819 (4)	0.3697 (3)	0.43803 (16)	0.0455 (6)
H11	0.3631	0.3584	0.4522	0.055*
C12	0.6075 (4)	0.3164 (3)	0.49798 (16)	0.0517 (7)
H12	0.5715	0.2695	0.5522	0.062*
C13	0.7847 (4)	0.3311 (3)	0.47934 (17)	0.0513 (7)
C14	0.8342 (4)	0.4020 (3)	0.39820 (18)	0.0566 (7)
H14	0.9531	0.4132	0.3842	0.068*
C15	0.7102 (3)	0.4562 (3)	0.33780 (16)	0.0505 (7)
H15	0.7461	0.5042	0.2838	0.061*
C16	0.9214 (5)	0.2747 (4)	0.5456 (2)	0.0805 (10)
H16A	0.8629	0.2348	0.5992	0.121*
H16B	0.9785	0.3498	0.5550	0.121*
H16C	1.0096	0.2038	0.5247	0.121*
C17	0.3103 (4)	0.8005 (4)	0.0171 (2)	0.0748 (9)
H17	0.3061	0.8620	0.0558	0.090*
C18	0.3617 (5)	0.8439 (5)	−0.0679 (3)	0.1067 (16)
H18	0.3889	0.9339	−0.0870	0.128*
C19	0.3723 (5)	0.7545 (6)	−0.1234 (3)	0.118 (2)
H19	0.4101	0.7814	−0.1813	0.142*
C20	0.3270 (4)	0.6220 (5)	−0.0949 (2)	0.0895 (13)
H20	0.3328	0.5596	−0.1331	0.107*
C21	0.2722 (3)	0.5840 (3)	−0.00735 (16)	0.0585 (8)
C22	0.2212 (3)	0.4456 (3)	0.03117 (18)	0.0554 (7)
C23	0.2133 (5)	0.3418 (5)	−0.0157 (2)	0.0829 (11)
H23	0.2405	0.3565	−0.0753	0.099*
C24	0.1654 (5)	0.2173 (5)	0.0259 (3)	0.0984 (15)
H24	0.1584	0.1474	−0.0054	0.118*
C25	0.1274 (4)	0.1953 (4)	0.1141 (3)	0.0843 (11)
H25	0.0972	0.1102	0.1435	0.101*
C26	0.1355 (4)	0.3035 (3)	0.1576 (2)	0.0640 (8)
H26	0.1088	0.2901	0.2173	0.077*
N1	0.2659 (3)	0.6739 (2)	0.04704 (14)	0.0531 (6)
N2	0.1801 (3)	0.4265 (2)	0.11749 (13)	0.0491 (5)
O1	0.0937 (3)	0.8418 (2)	0.21029 (14)	0.0713 (6)
O2	−0.0627 (2)	0.68095 (19)	0.19582 (11)	0.0527 (5)
O3	0.4440 (2)	0.57256 (18)	0.22078 (11)	0.0525 (5)
O4	0.2425 (2)	0.4705 (2)	0.30517 (12)	0.0621 (5)
Zn1	0.19260 (4)	0.59907 (3)	0.176739 (18)	0.04603 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0471 (16)	0.0555 (18)	0.0358 (13)	−0.0043 (13)	−0.0065 (11)	−0.0032 (12)
C2	0.0455 (15)	0.0373 (14)	0.0384 (13)	−0.0039 (11)	−0.0066 (11)	−0.0020 (11)
C3	0.0517 (16)	0.0425 (15)	0.0434 (14)	−0.0104 (12)	−0.0069 (12)	−0.0071 (12)
C4	0.0411 (15)	0.0476 (16)	0.0574 (16)	−0.0115 (12)	−0.0029 (12)	−0.0055 (13)
C5	0.0540 (17)	0.0377 (15)	0.0523 (15)	−0.0027 (12)	0.0000 (13)	−0.0018 (12)
C6	0.0627 (18)	0.0482 (16)	0.0517 (16)	−0.0059 (14)	−0.0093 (13)	−0.0170 (13)
C7	0.0457 (15)	0.0478 (16)	0.0545 (16)	−0.0062 (12)	−0.0113 (12)	−0.0117 (13)
C8	0.063 (2)	0.064 (2)	0.088 (2)	−0.0048 (16)	0.0114 (17)	−0.0212 (18)
C9	0.0499 (16)	0.0399 (15)	0.0460 (15)	−0.0036 (12)	−0.0021 (12)	−0.0166 (12)
C10	0.0483 (15)	0.0362 (14)	0.0381 (13)	−0.0069 (11)	−0.0014 (11)	−0.0104 (11)
C11	0.0501 (15)	0.0447 (15)	0.0435 (14)	−0.0115 (12)	0.0036 (12)	−0.0126 (12)
C12	0.0713 (19)	0.0448 (16)	0.0380 (14)	−0.0110 (14)	0.0028 (13)	−0.0072 (12)
C13	0.0602 (18)	0.0475 (16)	0.0468 (15)	−0.0029 (13)	−0.0108 (13)	−0.0108 (13)
C14	0.0454 (16)	0.0673 (19)	0.0563 (17)	−0.0121 (14)	−0.0045 (13)	−0.0052 (15)
C15	0.0521 (17)	0.0554 (17)	0.0419 (14)	−0.0128 (13)	−0.0012 (12)	−0.0005 (12)
C16	0.083 (2)	0.091 (3)	0.065 (2)	−0.002 (2)	−0.0273 (18)	−0.0045 (18)
C17	0.0556 (19)	0.076 (2)	0.075 (2)	−0.0037 (16)	0.0001 (16)	0.0213 (18)
C18	0.065 (2)	0.118 (4)	0.095 (3)	0.006 (2)	0.015 (2)	0.054 (3)
C19	0.071 (3)	0.170 (5)	0.060 (2)	0.035 (3)	0.019 (2)	0.051 (3)
C20	0.065 (2)	0.137 (4)	0.0404 (17)	0.038 (2)	0.0007 (15)	−0.005 (2)
C21	0.0404 (15)	0.085 (2)	0.0358 (14)	0.0209 (15)	−0.0045 (11)	−0.0023 (15)
C22	0.0424 (15)	0.071 (2)	0.0486 (16)	0.0188 (14)	−0.0149 (12)	−0.0199 (15)
C23	0.076 (2)	0.099 (3)	0.077 (2)	0.033 (2)	−0.0329 (19)	−0.052 (2)
C24	0.082 (3)	0.091 (3)	0.139 (4)	0.026 (2)	−0.050 (3)	−0.076 (3)
C25	0.066 (2)	0.060 (2)	0.134 (4)	−0.0004 (17)	−0.028 (2)	−0.033 (2)
C26	0.0607 (19)	0.0565 (19)	0.077 (2)	−0.0072 (15)	−0.0087 (15)	−0.0156 (17)
N1	0.0446 (13)	0.0597 (15)	0.0449 (13)	0.0013 (11)	0.0001 (10)	0.0051 (12)
N2	0.0439 (13)	0.0557 (14)	0.0469 (13)	−0.0007 (10)	−0.0046 (10)	−0.0127 (11)
O1	0.0465 (12)	0.0895 (16)	0.0860 (15)	−0.0154 (11)	−0.0004 (10)	−0.0336 (13)
O2	0.0564 (12)	0.0468 (11)	0.0540 (11)	−0.0047 (9)	0.0036 (9)	−0.0144 (9)
O3	0.0564 (12)	0.0522 (11)	0.0483 (10)	−0.0132 (9)	−0.0096 (9)	−0.0004 (9)
O4	0.0450 (11)	0.0880 (15)	0.0530 (11)	−0.0139 (10)	−0.0029 (9)	−0.0089 (10)
Zn1	0.0458 (2)	0.0512 (2)	0.04008 (18)	−0.00641 (14)	−0.00186 (12)	−0.00715 (13)

Geometric parameters (Å, º) top

C1—O1	1.244 (3)	C16—H16A	0.9600
C1—O2	1.270 (3)	C16—H16B	0.9600
C1—C2	1.496 (4)	C16—H16C	0.9600
C2—C7	1.383 (3)	C17—N1	1.332 (4)
C2—C3	1.384 (3)	C17—C18	1.366 (5)
C3—C4	1.378 (4)	C17—H17	0.9300
C3—H3	0.9300	C18—C19	1.339 (6)
C4—C5	1.381 (4)	C18—H18	0.9300
C4—H4	0.9300	C19—C20	1.384 (6)
C5—C6	1.393 (4)	C19—H19	0.9300
C5—C8	1.510 (4)	C20—C21	1.398 (4)
C6—C7	1.382 (4)	C20—H20	0.9300
C6—H6	0.9300	C21—N1	1.334 (4)
C7—H7	0.9300	C21—C22	1.480 (4)
C8—H8A	0.9600	C22—N2	1.349 (3)
C8—H8B	0.9600	C22—C23	1.380 (4)
C8—H8C	0.9600	C23—C24	1.364 (6)
C9—O4	1.254 (3)	C23—H23	0.9300
C9—O3	1.272 (3)	C24—C25	1.372 (6)
C9—C10	1.485 (3)	C24—H24	0.9300
C10—C11	1.383 (3)	C25—C26	1.383 (4)
C10—C15	1.384 (3)	C25—H25	0.9300
C11—C12	1.382 (4)	C26—N2	1.336 (4)
C11—H11	0.9300	C26—H26	0.9300
C12—C13	1.377 (4)	N1—Zn1	2.090 (2)
C12—H12	0.9300	N2—Zn1	2.103 (2)
C13—C14	1.384 (4)	O1—Zn1	2.509 (2)
C13—C16	1.514 (4)	O2—Zn1	1.9852 (18)
C14—C15	1.380 (4)	O3—Zn1	2.0626 (17)
C14—H14	0.9300	O4—Zn1	2.2058 (19)
C15—H15	0.9300

O1—C1—O2	121.5 (3)	N1—C17—C18	122.8 (4)
O1—C1—C2	120.6 (2)	N1—C17—H17	118.6
O2—C1—C2	117.8 (2)	C18—C17—H17	118.6
C7—C2—C3	118.5 (2)	C19—C18—C17	118.8 (4)
C7—C2—C1	120.8 (2)	C19—C18—H18	120.6
C3—C2—C1	120.7 (2)	C17—C18—H18	120.6
C4—C3—C2	121.0 (2)	C18—C19—C20	120.2 (4)
C4—C3—H3	119.5	C18—C19—H19	119.9
C2—C3—H3	119.5	C20—C19—H19	119.9
C3—C4—C5	121.1 (2)	C19—C20—C21	118.6 (4)
C3—C4—H4	119.5	C19—C20—H20	120.7
C5—C4—H4	119.5	C21—C20—H20	120.7
C4—C5—C6	117.8 (2)	N1—C21—C20	120.1 (3)
C4—C5—C8	121.5 (3)	N1—C21—C22	116.0 (2)
C6—C5—C8	120.7 (3)	C20—C21—C22	123.8 (3)
C7—C6—C5	121.1 (2)	N2—C22—C23	121.0 (3)
C7—C6—H6	119.4	N2—C22—C21	115.0 (2)
C5—C6—H6	119.4	C23—C22—C21	124.0 (3)
C6—C7—C2	120.4 (2)	C24—C23—C22	119.6 (4)
C6—C7—H7	119.8	C24—C23—H23	120.2
C2—C7—H7	119.8	C22—C23—H23	120.2
C5—C8—H8A	109.5	C23—C24—C25	120.0 (3)
C5—C8—H8B	109.5	C23—C24—H24	120.0
H8A—C8—H8B	109.5	C25—C24—H24	120.0
C5—C8—H8C	109.5	C24—C25—C26	117.9 (4)
H8A—C8—H8C	109.5	C24—C25—H25	121.0
H8B—C8—H8C	109.5	C26—C25—H25	121.0
O4—C9—O3	118.9 (2)	N2—C26—C25	122.6 (3)
O4—C9—C10	121.1 (2)	N2—C26—H26	118.7
O3—C9—C10	119.9 (2)	C25—C26—H26	118.7
C11—C10—C15	118.8 (2)	C17—N1—C21	119.5 (3)
C11—C10—C9	120.6 (2)	C17—N1—Zn1	124.7 (2)
C15—C10—C9	120.6 (2)	C21—N1—Zn1	115.76 (18)
C12—C11—C10	120.1 (2)	C26—N2—C22	118.8 (3)
C12—C11—H11	120.0	C26—N2—Zn1	125.87 (19)
C10—C11—H11	120.0	C22—N2—Zn1	115.32 (19)
C13—C12—C11	121.6 (2)	C1—O2—Zn1	101.97 (16)
C13—C12—H12	119.2	C9—O3—Zn1	92.93 (15)
C11—C12—H12	119.2	C9—O4—Zn1	86.93 (15)
C12—C13—C14	117.9 (2)	O1—Zn1—O2	57.03 (7)
C12—C13—C16	121.5 (3)	O1—Zn1—O3	95.86 (7)
C14—C13—C16	120.6 (3)	O1—Zn1—O4	103.13 (7)
C15—C14—C13	121.1 (3)	O1—Zn1—N1	92.92 (7)
C15—C14—H14	119.4	O1—Zn1—N2	155.41 (8)
C13—C14—H14	119.4	O2—Zn1—O3	145.10 (8)
C14—C15—C10	120.4 (2)	O2—Zn1—N1	105.58 (8)
C14—C15—H15	119.8	O3—Zn1—N1	96.58 (8)
C10—C15—H15	119.8	O2—Zn1—N2	103.12 (8)
C13—C16—H16A	109.5	O3—Zn1—N2	107.73 (8)
C13—C16—H16B	109.5	N1—Zn1—N2	77.88 (9)
H16A—C16—H16B	109.5	O2—Zn1—O4	100.93 (7)
C13—C16—H16C	109.5	O3—Zn1—O4	61.19 (7)
H16A—C16—H16C	109.5	N1—Zn1—O4	153.43 (8)
H16B—C16—H16C	109.5	N2—Zn1—O4	94.46 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3ⁱ	0.93	2.53	3.293 (3)	139
C4—H4···O1ⁱ	0.93	2.48	3.385 (3)	165
C14—H14···O4ⁱⁱ	0.93	2.51	3.417 (3)	164
C15—H15···O2ⁱⁱ	0.93	2.57	3.395 (3)	148
C20—H20···O3ⁱⁱⁱ	0.93	2.43	3.189 (4)	139
C23—H23···O2^iv	0.93	2.56	3.230 (4)	129

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

Experimental details

Crystal data
Chemical formula	[Zn(C₈H₇O₂)₂(C₁₀H₈N₂)]
M_r	491.83
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.6172 (3), 9.8211 (4), 15.7595 (6)
α, β, γ (°)	79.130 (2), 83.977 (2), 79.958 (2)
V (Å³)	1136.90 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.12
Crystal size (mm)	0.26 × 0.23 × 0.21

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.760, 0.800
No. of measured, independent and observed [I > 2σ(I)] reflections	10295, 4047, 3281
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.087, 1.02
No. of reflections	4047
No. of parameters	300
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.29

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

N1—Zn1	2.090 (2)	O2—Zn1	1.9852 (18)
N2—Zn1	2.103 (2)	O3—Zn1	2.0626 (17)
O1—Zn1	2.509 (2)	O4—Zn1	2.2058 (19)

O1—Zn1—O2	57.03 (7)	O2—Zn1—N2	103.12 (8)
O1—Zn1—O3	95.86 (7)	O3—Zn1—N2	107.73 (8)
O1—Zn1—O4	103.13 (7)	N1—Zn1—N2	77.88 (9)
O1—Zn1—N1	92.92 (7)	O2—Zn1—O4	100.93 (7)
O1—Zn1—N2	155.41 (8)	O3—Zn1—O4	61.19 (7)
O2—Zn1—O3	145.10 (8)	N1—Zn1—O4	153.43 (8)
O2—Zn1—N1	105.58 (8)	N2—Zn1—O4	94.46 (8)
O3—Zn1—N1	96.58 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3ⁱ	0.93	2.53	3.293 (3)	139
C4—H4···O1ⁱ	0.93	2.48	3.385 (3)	165
C14—H14···O4ⁱⁱ	0.93	2.51	3.417 (3)	164
C15—H15···O2ⁱⁱ	0.93	2.57	3.395 (3)	148
C20—H20···O3ⁱⁱⁱ	0.93	2.43	3.189 (4)	139
C23—H23···O2^iv	0.93	2.56	3.230 (4)	129

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

Acknowledgements

The author acknowledges Mudanjiang Normal College for supporting this work.

References

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