catena-Poly[[(4-formyl­benzoato-κO1)(isonicotinamide-κN1)zinc(II)]-μ-4-formyl­benzoato-κ2O1:O1′]

Hökelek, T.; Yılmaz, F.; Tercan, B.; Sertçelik, M.; Necefoğlu, H.

doi:10.1107/S160053680904241X

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Pages m1399-m1400

https://doi.org/10.1107/S160053680904241X

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catena-Poly[[(4-formylbenzoato-κO¹)(isonicotinamide-κN¹)zinc(II)]-μ-4-formylbenzoato-κ²O¹:O^1′]

Tuncer Hökelek,^a ^* Filiz Yılmaz,^b Barış Tercan,^c Mustafa Sertçelik ^d and Hacali Necefoğlu ^d

^aDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey, ^bDepartment of Chemistry, Faculty of Science, Anadolu University, 26470 Yenibağlar, Eskişehir, Turkey, ^cDepartment of Physics, Karabük University, 78050 Karabük, Turkey, and ^dDepartment of Chemistry, Kafkas University, 63100 Kars, Turkey
^*Correspondence e-mail: merzifon@hacettepe.edu.tr

(Received 14 October 2009; accepted 15 October 2009; online 23 October 2009)

In the title compound, [Zn(C₈H₅O₃)₂(C₆H₆N₂O)]_n, the Zn^II ion is tetrahedrally coordinated by two formylbenzoate (FB) and one isonicotinamide (INA) ligands while symmetry-related FB ligands bridge adjacent Zn^II ions, forming polymeric chains along the b axis. The carboxylate groups in the two FB ions are twisted away from the attached benzene ring by 9.07 (2) and 26.2 (2)°. The two benzene rings of the FB ions are oriented at a dihedral angle of 81.30 (5)°. In the crystal, adjacent polymeric chains interact via N—H⋯O and C—H⋯O hydrogen bonds, π–π contacts between the formylbenzoate rings [centroid–centroid distance = 3.7736 (8) Å] and weak C—H⋯π interactions, forming a three-dimensional network.

Related literature

For general background to niacin, see: Krishnamachari (1974 ). For the crystal structure of N,N-diethylnicotinamide, see: Bigoli et al. (1972 ). For related structures, see: Hökelek & Necefoğlu (1996 ); Hökelek et al. (2009 ).

Experimental

Crystal data

[Zn(C₈H₅O₃)₂(C₆H₆N₂O)]
M_r = 485.74
Monoclinic, P 2₁ /n
a = 13.3143 (2) Å
b = 6.7857 (1) Å
c = 21.3927 (3) Å
β = 91.458 (1)°
V = 1932.14 (5) Å³
Z = 4
Mo Kα radiation
μ = 1.32 mm⁻¹
T = 100 K
0.22 × 0.12 × 0.08 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.829, T_max = 0.903
17841 measured reflections
4812 independent reflections
4086 reflections with I > 2σ(I)
R_int = 0.072

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.080
S = 1.10
4812 reflections
297 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Selected bond lengths (Å)

Zn1—O1	1.9153 (11)
Zn1—O3	1.9723 (11)
Zn1—O4	1.9450 (10)
Zn1—N1	2.0270 (12)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2ⁱ	0.86	2.08	2.9242 (17)	165
N2—H2B⋯O2ⁱⁱ	0.86	2.11	2.9439 (17)	163
C4—H4⋯O5ⁱⁱⁱ	0.93	2.41	3.298 (2)	160
C6—H6⋯O7^iv	0.93	2.50	3.223 (2)	135
C15—H15⋯O6^iv	0.93	2.32	3.2049 (19)	159
C16—H16⋯O2ⁱⁱ	0.93	2.44	3.3541 (18)	169
C3—H3⋯Cg1	0.93	2.73	3.6332 (17)	163
Symmetry codes: (i) -x+2, -y, -z; (ii) x, y-1, z; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[-x+{\script{5\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ . Cg1 is the centroid of the C9–C14 ring.

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: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053680904241X/ci2939sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053680904241X/ci2939Isup2.hkl

checkCIF report

Comment top

As a part of our ongoing investigation on transition metal complexes of nicotinamide (NA), one form of niacin (Krishnamachari, 1974), and/or the nicotinic acid derivative N,N-diethylnicotinamide (DENA), an important respiratory stimulant (Bigoli et al., 1972), the title compound was synthesized and its crystal structure is reported herein.

In the crystal structure of the title compound, each Zn^II ion is coordinated by two formylbenzoate (FB) and one isonicotinamide (INA) ligands (Fig. 1), while symmetry related FB ligands bridge the Zn^II ions forming polymeric chains along the b axis (Fig.2). The structures of similar complexes of Zn^II ion, [Zn₂(C₁₀H₁₄N₂O)₂(C₇H₅O₃)₄].2H₂O (Hökelek & Necefouglu, 1996) and [Zn(C₉H₁₀NO₂)₂(C₆H₆N₂O)(H₂O)₂] (Hökelek et al., 2009) have also been reported.

The average Zn—O bond length (Table 1) is 1.9442 (11) Å and the Zn1 atom is displaced out of the least-squares planes of the carboxylate groups (O1/C1/O2) and (O3/C8/O4*) by 0.687 (5) Å and 0.703 (2) Å, respectively. The O1/C1/O2 and O3/C8/O4* carboxylate planes form dihedral angles of 9.07 (2)° and 26.2 (2)°, respectively, with benzene rings A(C2-C7) and B(C9-C14), while the angles between rings A, B and C (N1/C15-C19) are A/B = 81.30 (5), A/C = 63.17 (5) and B/C = 46.11 (5)°.

In the crystal structure, N—H···O and C—H···O hydrogen bonds (Table 2) link adjacent chains into a three-dimensional network. In addition, π–π contacts between symmetry related A(C2-C7) formylbenzoate rings at (x, y, z) and (5/2-x, -1/2+y, 1/2-z)/(5/2-x, 1/2+y, 1/2-z) with a centroid-to-centroid distance of 3.7736 (8) Å, and weak C—H···π interaction (Table 2) involving the B(C9-C14) ring stabilize the structure.

Related literature top

For general background to niacin, see: Krishnamachari (1974). For the crystal structure of N,N-diethylnicotinamide, see: Bigoli et al. (1972). For related structures, see: Hökelek & Necefouglu (1996); Hökelek et al. (2009). Cg1 is the centroid of the C9–C14 ring.

Experimental top

The title compound was prepared by the reaction of ZnSO₄.H₂O (0.90 g, 5 mmol) in H₂O (25 ml) and INA (1.22 g, 10 mmol) in H₂O (40 ml) with sodium 4-formylbenzoate (1.72 g, 10 mmol) in H₂O (50 ml). The mixture was filtered and set aside to crystallize at ambient temperature for several days, giving colourless single crystals.

Structure description top

For general background to niacin, see: Krishnamachari (1974). For the crystal structure of N,N-diethylnicotinamide, see: Bigoli et al. (1972). For related structures, see: Hökelek & Necefouglu (1996); Hökelek et al. (2009). Cg1 is the centroid of the C9–C14 ring.

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: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The asymmetric unit of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Part of a polymeric chain of the title compound.

catena-Poly[[(4-formylbenzoato-κO¹)(isonicotinamide- κN¹)zinc(II)]-µ-4-formylbenzoato-κ²O¹:O^1'] top

Crystal data top

[Zn(C₈H₅O₃)₂(C₆H₆N₂O)]	F(000) = 992
M_r = 485.74	D_x = 1.670 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9448 reflections
a = 13.3143 (2) Å	θ = 3.1–28.4°
b = 6.7857 (1) Å	µ = 1.32 mm⁻¹
c = 21.3927 (3) Å	T = 100 K
β = 91.458 (1)°	Needle, colourless
V = 1932.14 (5) Å³	0.22 × 0.12 × 0.08 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	4812 independent reflections
Radiation source: fine-focus sealed tube	4086 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.072
φ and ω scans	θ_max = 28.4°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −17→14
T_min = 0.829, T_max = 0.903	k = −8→9
17841 measured reflections	l = −28→28

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.080	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ²(F_o²) + (0.0394P)² + 0.0092P] where P = (F_o² + 2F_c²)/3
4812 reflections	(Δ/σ)_max = 0.001
297 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

[Zn(C₈H₅O₃)₂(C₆H₆N₂O)]	V = 1932.14 (5) Å³
M_r = 485.74	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.3143 (2) Å	µ = 1.32 mm⁻¹
b = 6.7857 (1) Å	T = 100 K
c = 21.3927 (3) Å	0.22 × 0.12 × 0.08 mm
β = 91.458 (1)°

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	4812 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	4086 reflections with I > 2σ(I)
T_min = 0.829, T_max = 0.903	R_int = 0.072
17841 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.080	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 0.47 e Å⁻³
4812 reflections	Δρ_min = −0.39 e Å⁻³
297 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	0.816160 (13)	0.51300 (2)	0.187880 (8)	0.01058 (7)
O1	0.95052 (8)	0.60767 (16)	0.20123 (5)	0.0149 (2)
O2	1.00643 (8)	0.55706 (16)	0.10502 (5)	0.0149 (2)
O3	0.77863 (8)	0.37932 (15)	0.26575 (5)	0.0134 (2)
O4	0.70741 (8)	0.67550 (14)	0.15404 (5)	0.0137 (2)
O5	0.83582 (11)	−0.07543 (19)	−0.07713 (6)	0.0312 (3)
O6	1.49773 (9)	0.61367 (17)	0.23858 (5)	0.0199 (3)
O7	1.10801 (11)	0.97953 (16)	0.45862 (6)	0.0236 (3)
N1	0.81632 (9)	0.29546 (17)	0.12295 (6)	0.0112 (3)
N2	0.91501 (11)	−0.28715 (18)	−0.01158 (6)	0.0182 (3)
H2A	0.9269	−0.3695	−0.0410	0.022*
H2B	0.9348	−0.3125	0.0262	0.022*
C1	1.02044 (11)	0.5821 (2)	0.16202 (7)	0.0110 (3)
C2	1.12564 (11)	0.5862 (2)	0.18971 (7)	0.0109 (3)
C3	1.14051 (12)	0.5879 (2)	0.25423 (7)	0.0126 (3)
H3	1.0857	0.5867	0.2803	0.015*
C4	1.23802 (12)	0.5913 (2)	0.27978 (7)	0.0131 (3)
H4	1.2487	0.5906	0.3229	0.016*
C5	1.31866 (11)	0.5957 (2)	0.24033 (7)	0.0122 (3)
C6	1.30379 (12)	0.5942 (2)	0.17551 (7)	0.0143 (3)
H6	1.3585	0.5979	0.1494	0.017*
C7	1.20746 (12)	0.5872 (2)	0.15043 (7)	0.0134 (3)
H7	1.1971	0.5832	0.1073	0.016*
C8	0.81930 (11)	0.3293 (2)	0.31722 (7)	0.0115 (3)
C9	0.89783 (12)	0.4527 (2)	0.34954 (7)	0.0114 (3)
C10	0.96360 (12)	0.3649 (2)	0.39317 (7)	0.0149 (3)
H10	0.9603	0.2299	0.4004	0.018*
C11	1.03354 (13)	0.4785 (2)	0.42548 (8)	0.0162 (3)
H11	1.0792	0.4188	0.4531	0.019*
C12	1.03609 (12)	0.6823 (2)	0.41700 (7)	0.0140 (3)
C13	0.97104 (12)	0.7698 (2)	0.37288 (7)	0.0138 (3)
H13	0.9730	0.9053	0.3666	0.017*
C14	0.90409 (12)	0.6556 (2)	0.33872 (7)	0.0122 (3)
H14	0.8627	0.7138	0.3083	0.015*
C15	0.86757 (11)	0.1289 (2)	0.13520 (7)	0.0125 (3)
H15	0.8924	0.1074	0.1757	0.015*
C16	0.88489 (13)	−0.0119 (2)	0.09003 (8)	0.0139 (3)
H16	0.9213	−0.1251	0.1000	0.017*
C17	0.84719 (12)	0.0179 (2)	0.02948 (8)	0.0126 (3)
C18	0.79165 (12)	0.1872 (2)	0.01756 (7)	0.0147 (3)
H18	0.7639	0.2097	−0.0221	0.018*
C19	0.77770 (12)	0.3220 (2)	0.06473 (7)	0.0136 (3)
H19	0.7404	0.4350	0.0561	0.016*
C20	0.86597 (12)	−0.1204 (2)	−0.02441 (7)	0.0157 (3)
C21	1.42128 (13)	0.6036 (2)	0.26818 (8)	0.0161 (3)
H21	1.4266 (13)	0.600 (3)	0.3157 (9)	0.028 (5)*
C22	1.10601 (13)	0.8010 (2)	0.45686 (8)	0.0188 (4)
H22	1.1561 (13)	0.714 (3)	0.4842 (9)	0.020 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.01001 (11)	0.01290 (10)	0.00882 (11)	0.00080 (6)	−0.00023 (7)	−0.00111 (6)
O1	0.0092 (6)	0.0225 (6)	0.0129 (5)	−0.0007 (4)	0.0003 (4)	−0.0045 (4)
O2	0.0144 (6)	0.0195 (5)	0.0106 (5)	0.0021 (5)	−0.0019 (5)	−0.0020 (4)
O3	0.0120 (6)	0.0184 (5)	0.0098 (5)	−0.0013 (4)	−0.0021 (4)	0.0016 (4)
O4	0.0134 (6)	0.0141 (5)	0.0135 (5)	0.0030 (4)	−0.0013 (5)	−0.0022 (4)
O5	0.0524 (9)	0.0310 (7)	0.0097 (6)	0.0163 (7)	−0.0092 (6)	−0.0050 (5)
O6	0.0130 (6)	0.0295 (6)	0.0172 (6)	−0.0013 (5)	−0.0005 (5)	0.0005 (5)
O7	0.0279 (8)	0.0248 (6)	0.0181 (7)	−0.0107 (5)	0.0007 (6)	−0.0038 (5)
N1	0.0094 (7)	0.0145 (6)	0.0096 (6)	−0.0011 (5)	−0.0002 (5)	0.0003 (5)
N2	0.0256 (8)	0.0193 (6)	0.0094 (6)	0.0055 (6)	−0.0018 (6)	−0.0037 (5)
C1	0.0111 (8)	0.0103 (6)	0.0115 (7)	0.0008 (6)	−0.0008 (6)	−0.0005 (6)
C2	0.0111 (8)	0.0102 (6)	0.0113 (7)	0.0000 (6)	−0.0016 (6)	0.0001 (6)
C3	0.0128 (8)	0.0145 (7)	0.0106 (7)	0.0009 (6)	0.0017 (6)	0.0001 (6)
C4	0.0164 (8)	0.0143 (7)	0.0085 (7)	0.0000 (6)	−0.0008 (6)	−0.0002 (6)
C5	0.0121 (8)	0.0110 (7)	0.0135 (8)	0.0003 (6)	−0.0016 (6)	0.0002 (6)
C6	0.0113 (8)	0.0190 (7)	0.0127 (7)	−0.0008 (6)	0.0028 (6)	−0.0003 (6)
C7	0.0143 (8)	0.0183 (7)	0.0076 (7)	0.0006 (6)	−0.0008 (6)	0.0006 (6)
C8	0.0096 (8)	0.0138 (7)	0.0113 (7)	0.0029 (6)	0.0015 (6)	−0.0023 (6)
C9	0.0098 (8)	0.0154 (7)	0.0091 (7)	−0.0002 (6)	0.0015 (6)	−0.0020 (6)
C10	0.0173 (9)	0.0137 (7)	0.0137 (8)	0.0002 (6)	−0.0001 (7)	−0.0003 (6)
C11	0.0144 (9)	0.0206 (8)	0.0134 (8)	0.0021 (6)	−0.0043 (7)	−0.0003 (6)
C12	0.0113 (8)	0.0191 (7)	0.0117 (7)	−0.0021 (6)	−0.0004 (6)	−0.0029 (6)
C13	0.0149 (8)	0.0136 (7)	0.0129 (7)	−0.0015 (6)	0.0041 (6)	−0.0024 (6)
C14	0.0111 (8)	0.0164 (7)	0.0090 (7)	0.0020 (6)	0.0012 (6)	0.0004 (6)
C15	0.0116 (8)	0.0171 (7)	0.0087 (7)	0.0004 (6)	−0.0023 (6)	0.0008 (6)
C16	0.0157 (9)	0.0140 (7)	0.0120 (8)	0.0026 (6)	−0.0017 (7)	−0.0003 (5)
C17	0.0147 (8)	0.0143 (7)	0.0088 (8)	−0.0022 (6)	0.0006 (6)	−0.0003 (5)
C18	0.0169 (9)	0.0176 (7)	0.0094 (7)	−0.0006 (6)	−0.0029 (6)	0.0014 (6)
C19	0.0130 (8)	0.0150 (7)	0.0128 (7)	0.0019 (6)	−0.0011 (6)	0.0029 (6)
C20	0.0180 (9)	0.0185 (7)	0.0106 (7)	0.0001 (6)	−0.0013 (7)	−0.0024 (6)
C21	0.0173 (9)	0.0171 (7)	0.0139 (8)	0.0003 (6)	−0.0024 (7)	−0.0003 (6)
C22	0.0174 (9)	0.0260 (8)	0.0131 (8)	−0.0046 (7)	0.0007 (7)	−0.0018 (7)

Geometric parameters (Å, º) top

Zn1—O1	1.9153 (11)	C7—C6	1.378 (2)
Zn1—O3	1.9723 (11)	C7—H7	0.93
Zn1—O4	1.9450 (10)	C8—O4ⁱⁱ	1.2669 (18)
Zn1—N1	2.0270 (12)	C8—C9	1.495 (2)
O1—C1	1.2807 (18)	C9—C10	1.397 (2)
O2—C1	1.2405 (18)	C9—C14	1.3990 (19)
O3—C8	1.2611 (17)	C10—H10	0.93
O4—C8ⁱ	1.2669 (18)	C11—C10	1.381 (2)
O5—C20	1.2261 (18)	C11—H11	0.93
O6—C21	1.214 (2)	C12—C11	1.395 (2)
O7—C22	1.2124 (19)	C12—C13	1.397 (2)
N1—C15	1.3427 (18)	C12—C22	1.484 (2)
N1—C19	1.3474 (18)	C13—C14	1.377 (2)
N2—C20	1.332 (2)	C13—H13	0.93
N2—H2A	0.86	C14—H14	0.93
N2—H2B	0.86	C15—H15	0.93
C2—C1	1.507 (2)	C16—C15	1.382 (2)
C2—C3	1.390 (2)	C16—C17	1.392 (2)
C2—C7	1.393 (2)	C16—H16	0.93
C3—C4	1.396 (2)	C18—C17	1.386 (2)
C3—H3	0.93	C18—H18	0.93
C4—H4	0.93	C19—C18	1.378 (2)
C5—C4	1.383 (2)	C19—H19	0.93
C5—C6	1.396 (2)	C20—C17	1.512 (2)
C5—C21	1.478 (2)	C21—H21	1.018 (19)
C6—H6	0.93	C22—H22	1.057 (17)

O1—Zn1—O3	106.50 (4)	C14—C9—C8	121.23 (13)
O1—Zn1—O4	123.30 (5)	C9—C10—H10	120.0
O1—Zn1—N1	109.22 (5)	C11—C10—C9	119.95 (14)
O3—Zn1—N1	104.39 (5)	C11—C10—H10	120.0
O4—Zn1—O3	111.89 (5)	C10—C11—C12	120.45 (15)
O4—Zn1—N1	99.88 (5)	C10—C11—H11	119.8
C1—O1—Zn1	123.27 (10)	C12—C11—H11	119.8
C8—O3—Zn1	138.48 (10)	C11—C12—C13	119.50 (14)
C8ⁱ—O4—Zn1	120.13 (10)	C11—C12—C22	118.70 (15)
C15—N1—Zn1	119.26 (10)	C13—C12—C22	121.77 (14)
C15—N1—C19	118.22 (13)	C12—C13—H13	120.0
C19—N1—Zn1	121.95 (10)	C14—C13—C12	120.09 (14)
C20—N2—H2A	120.0	C14—C13—H13	120.0
C20—N2—H2B	120.0	C9—C14—H14	119.8
H2A—N2—H2B	120.0	C13—C14—C9	120.42 (14)
O1—C1—C2	115.07 (13)	C13—C14—H14	119.8
O2—C1—O1	124.67 (14)	N1—C15—C16	122.57 (14)
O2—C1—C2	120.25 (14)	N1—C15—H15	118.7
C3—C2—C1	119.87 (14)	C16—C15—H15	118.7
C3—C2—C7	120.36 (14)	C15—C16—C17	119.19 (14)
C7—C2—C1	119.76 (13)	C15—C16—H16	120.4
C2—C3—C4	119.77 (14)	C17—C16—H16	120.4
C2—C3—H3	120.1	C16—C17—C20	123.82 (13)
C4—C3—H3	120.1	C18—C17—C16	118.00 (14)
C3—C4—H4	120.3	C18—C17—C20	118.16 (14)
C5—C4—C3	119.36 (14)	C17—C18—H18	120.1
C5—C4—H4	120.3	C19—C18—C17	119.77 (14)
C4—C5—C6	120.90 (14)	C19—C18—H18	120.1
C4—C5—C21	118.62 (14)	N1—C19—C18	122.20 (14)
C6—C5—C21	120.48 (14)	N1—C19—H19	118.9
C5—C6—H6	120.2	C18—C19—H19	118.9
C7—C6—C5	119.60 (14)	O5—C20—N2	123.26 (15)
C7—C6—H6	120.2	O5—C20—C17	119.35 (14)
C2—C7—H7	120.0	N2—C20—C17	117.39 (13)
C6—C7—C2	119.98 (14)	O6—C21—C5	124.78 (15)
C6—C7—H7	120.0	O6—C21—H21	119.0 (11)
O3—C8—O4ⁱⁱ	121.72 (14)	C5—C21—H21	116.3 (11)
O3—C8—C9	122.19 (13)	O7—C22—C12	124.98 (17)
O4ⁱⁱ—C8—C9	116.01 (13)	O7—C22—H22	121.9 (9)
C10—C9—C8	119.27 (13)	C12—C22—H22	113.1 (9)
C10—C9—C14	119.45 (14)

O3—Zn1—O1—C1	132.27 (11)	C21—C5—C4—C3	178.69 (13)
O4—Zn1—O1—C1	−96.44 (12)	C4—C5—C6—C7	−0.3 (2)
N1—Zn1—O1—C1	20.07 (13)	C21—C5—C6—C7	−179.85 (14)
O1—Zn1—O3—C8	−6.56 (15)	C4—C5—C21—O6	−177.81 (15)
O4—Zn1—O3—C8	−143.97 (14)	C6—C5—C21—O6	1.7 (2)
N1—Zn1—O3—C8	108.94 (15)	C2—C7—C6—C5	1.5 (2)
O1—Zn1—O4—C8ⁱ	−60.90 (13)	O3—C8—C9—C10	−158.23 (15)
O3—Zn1—O4—C8ⁱ	68.17 (12)	O3—C8—C9—C14	24.3 (2)
N1—Zn1—O4—C8ⁱ	178.16 (11)	O4ⁱⁱ—C8—C9—C10	24.8 (2)
O1—Zn1—N1—C15	62.86 (12)	O4ⁱⁱ—C8—C9—C14	−152.61 (15)
O1—Zn1—N1—C19	−108.32 (12)	C8—C9—C10—C11	−177.06 (15)
O3—Zn1—N1—C15	−50.72 (12)	C14—C9—C10—C11	0.4 (2)
O3—Zn1—N1—C19	138.10 (12)	C8—C9—C14—C13	174.28 (14)
O4—Zn1—N1—C15	−166.53 (11)	C10—C9—C14—C13	−3.2 (2)
O4—Zn1—N1—C19	22.29 (13)	C12—C11—C10—C9	2.9 (3)
Zn1—O1—C1—O2	25.4 (2)	C13—C12—C11—C10	−3.6 (3)
Zn1—O1—C1—C2	−155.21 (9)	C22—C12—C11—C10	174.41 (16)
Zn1—O3—C8—O4ⁱⁱ	−147.48 (12)	C11—C12—C13—C14	0.9 (2)
Zn1—O3—C8—C9	35.8 (2)	C22—C12—C13—C14	−177.08 (15)
Zn1—N1—C15—C16	−169.24 (12)	C11—C12—C22—O7	−171.97 (17)
C19—N1—C15—C16	2.3 (2)	C13—C12—C22—O7	6.0 (3)
Zn1—N1—C19—C18	169.38 (12)	C12—C13—C14—C9	2.5 (2)
C15—N1—C19—C18	−1.9 (2)	C17—C16—C15—N1	−0.7 (2)
C3—C2—C1—O1	9.2 (2)	C15—C16—C17—C18	−1.4 (2)
C3—C2—C1—O2	−171.42 (14)	C15—C16—C17—C20	176.70 (15)
C7—C2—C1—O1	−171.18 (13)	C19—C18—C17—C16	1.7 (2)
C7—C2—C1—O2	8.2 (2)	C19—C18—C17—C20	−176.45 (14)
C1—C2—C3—C4	179.87 (13)	N1—C19—C18—C17	−0.1 (2)
C7—C2—C3—C4	0.2 (2)	N2—C20—C17—C16	5.3 (2)
C1—C2—C7—C6	178.94 (14)	N2—C20—C17—C18	−176.65 (15)
C3—C2—C7—C6	−1.4 (2)	O5—C20—C17—C16	−174.85 (17)
C2—C3—C4—C5	0.9 (2)	O5—C20—C17—C18	3.2 (2)
C6—C5—C4—C3	−0.8 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2ⁱⁱⁱ	0.86	2.08	2.9242 (17)	165
N2—H2B···O2^iv	0.86	2.11	2.9439 (17)	163
C4—H4···O5^v	0.93	2.41	3.298 (2)	160
C6—H6···O7^vi	0.93	2.50	3.223 (2)	135
C15—H15···O6^vi	0.93	2.32	3.2049 (19)	159
C16—H16···O2^iv	0.93	2.44	3.3541 (18)	169
C3—H3···Cg1	0.93	2.73	3.6332 (17)	163

Symmetry codes: (iii) −x+2, −y, −z; (iv) x, y−1, z; (v) x+1/2, −y+1/2, z+1/2; (vi) −x+5/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Zn(C₈H₅O₃)₂(C₆H₆N₂O)]
M_r	485.74
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	13.3143 (2), 6.7857 (1), 21.3927 (3)
β (°)	91.458 (1)
V (Å³)	1932.14 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.32
Crystal size (mm)	0.22 × 0.12 × 0.08

Data collection
Diffractometer	Bruker Kappa APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.829, 0.903
No. of measured, independent and observed [I > 2σ(I)] reflections	17841, 4812, 4086
R_int	0.072
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.080, 1.10
No. of reflections	4812
No. of parameters	297
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.39

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Selected bond lengths (Å) top

Zn1—O1	1.9153 (11)	Zn1—O4	1.9450 (10)
Zn1—O3	1.9723 (11)	Zn1—N1	2.0270 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2ⁱ	0.86	2.08	2.9242 (17)	165
N2—H2B···O2ⁱⁱ	0.86	2.11	2.9439 (17)	163
C4—H4···O5ⁱⁱⁱ	0.93	2.41	3.298 (2)	160
C6—H6···O7^iv	0.93	2.50	3.223 (2)	135
C15—H15···O6^iv	0.93	2.32	3.2049 (19)	159
C16—H16···O2ⁱⁱ	0.93	2.44	3.3541 (18)	169
C3—H3···Cg1	0.93	2.73	3.6332 (17)	163

Symmetry codes: (i) −x+2, −y, −z; (ii) x, y−1, z; (iii) x+1/2, −y+1/2, z+1/2; (iv) −x+5/2, y−1/2, −z+1/2.

Acknowledgements

The authors are indebted to Anadolu University and the Medicinal Plants and Medicine Research Centre of Anadolu University, Eskişehir, Turkey, for the use of the X-ray diffractometer. This work was supported financially by Kafkas University Research Fund (grant No. 2009-FEF-03).

References

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