Diaqua­bis(2-bromo­benzoato-κO)bis­(N,N-diethyl­nicotinamide-κN1)zinc(II)

Hökelek, T.; Dal, H.; Tercan, B.; Özbek, F.E.; Necefoğlu, H.

doi:10.1107/S160053680901191X

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Pages m481-m482

doi:10.1107/S160053680901191X

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Diaquabis(2-bromobenzoato-κO)bis(N,N-diethylnicotinamide-κN¹)zinc(II)

Tuncer Hökelek,^a Hakan Dal,^b Barış Tercan,^c F. Elif Özbek ^d and Hacali Necefoğlu ^d ^*

^aHacettepe University, Department of Physics, 06800 Beytepe, Ankara, Turkey, ^bAnadolu University, Faculty of Science, Department of Chemistry, 26470 Yenibağlar, Eskişehir, Turkey, ^cKarabük University, Department of Physics, 78050 Karabük, Turkey, and ^dKafkas University, Department of Chemistry, 63100 Kars, Turkey
^*Correspondence e-mail: merzifon@hacettepe.edu.tr

(Received 27 March 2009; accepted 31 March 2009; online 2 April 2009)

In the centrosymmetric title complex, [Zn(C₇H₄BrO₂)₂(C₁₀H₁₄N₂O)₂(H₂O)₂], the Zn^II atom is located on an inversion center. The asymmetric unit contains one 2-bromobenzoate (BB), one diethylnicotinamide (DENA) ligand and one coordinating water molecule. The four O atoms in the equatorial plane around the Zn atom form a slightly distorted square-planar arrangement, while the slightly distorted octahedral coordination is completed by the two N atoms of the DENA ligands in the axial positions. The dihedral angle between the carboxyl group and the adjacent benzene ring is 85.51 (12)°, while the pyridine and benzene rings are oriented at a dihedral angle of 44.07 (6)°. In the crystal structure, O—H⋯O hydrogen bonds link the molecules into infinite chains.

Related literature

For general backgroud, see: Antolini et al. (1982 ); Bigoli et al. (1972 ); Nadzhafov et al. (1981 ); Shnulin et al. (1981 ). For related structures, see: Hökelek et al. (1995 , 1997 , 2007 2008 ); (Hökelek & Necefoğlu (1996 , 1997 , 2007 ).

Experimental

Crystal data

[Zn(C₇H₄BrO₂)₂(C₁₀H₁₄N₂O)₂(H₂O)₂]
M_r = 857.91
Monoclinic, P 2₁ /n
a = 13.0037 (2) Å
b = 10.3387 (2) Å
c = 14.9365 (3) Å
β = 114.180 (1)°
V = 1831.90 (6) Å³
Z = 2
Mo Kα radiation
μ = 2.91 mm⁻¹
T = 100 K
0.40 × 0.30 × 0.23 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.368, T_max = 0.517
16722 measured reflections
4566 independent reflections
3769 reflections with I > 2σ(I)
R_int = 0.072

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.073
S = 0.98
4566 reflections
232 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.13 e Å⁻³
Δρ_min = −0.53 e Å⁻³

Table 1
Selected bond lengths (Å)

Zn1—O1	2.0600 (12)
Zn1—O4	2.1269 (12)
Zn1—N1	2.1962 (14)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H41⋯O3ⁱ	0.88 (2)	1.88 (2)	2.7518 (18)	168 (3)
O4—H42⋯O2ⁱⁱ	0.87 (2)	1.81 (2)	2.640 (2)	158 (2)
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -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: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680901191X/xu2502sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680901191X/xu2502Isup2.hkl

checkCIF report

Comment top

Transition metal complexes with biochemically active ligands frequently show interesting physical and/or chemical properties, as a result they may find applications in biological systems (Antolini et al., 1982). The structural functions and coordination relationships of the arylcarboxylate ion in transition metal complexes of benzoic acid derivatives change depending on the nature and position of the substituent groups on the benzene ring, the nature of the additional ligand molecule or solvent, and the medium of the synthesis (Nadzhafov et al., 1981; Shnulin et al., 1981). The nicotinic acid derivative N,N-diethylnicotinamide (DENA) is an important respiratory stimulant (Bigoli et al., 1972).

The structure determination of the title compound, (I), a zinc complex with two 2-bromobenzoate (BB), two diethylnicotinamide (DENA) ligands and two water molecules, was undertaken in order to determine the properties of the ligands and also to compare the results obtained with those reported previously.

Compound (I) is a monomeric complex, with the Zn atom on a centre of symmetry. It contains two BB, two DENA ligands and two water molecules (Fig. 1). All ligands are monodentate. The four O atoms (O1, O4, and the symmetry-related atoms, O1', O4') in the equatorial plane around the Zn atom form a slightly distorted square-planar arrangement, while the slightly distorted octahedral coordination is completed by the two N atoms of the DENA ligands (N1, N1') in the axial positions (Table 1 and Fig. 1).

The near equality of the C1—O1 [1.263 (2) Å] and C1—O2 [1.240 (2) Å] bonds in the carboxylate group indicates a delocalized bonding arrangement, rather than localized single and double bonds, and may be compared with the corresponding distances: 1.256 (6) and 1.245 (6) Å in [Mn(DENA)₂(C₇H₄ClO₂)₂(H₂O)₂] (Hökelek et al., 2008), 1.265 (6) and 1.275 (6) Å in [Mn(C₉H₁₀NO₂)₂(H₂O)₄].2(H₂O) (Hökelek & Necefoğlu, 2007), 1.260 (4) and 1.252 (4) Å in [Zn(DENA)₂(C₇H₄FO₂)₂(H₂O)₂] (Hökelek et al., 2007), 1.259 (9) and 1.273 (9) Å in Cu₂(DENA)₂(C₆H₅COO)₄ (Hökelek et al., 1995), 1.279 (4) and 1.246 (4) Å in [Zn₂(DENA)₂(C₇H₅O₃)₄].2H₂O (Hökelek & Necefoğlu, 1996), 1.251 (6) and 1.254 (7) Å in [Co(DENA)₂(C₇H₅O₃)₂(H₂O)₂] (Hökelek & Necefoğlu, 1997) and 1.278 (3) and 1.246 (3) Å in [Cu(DENA)₂(C₇H₄NO₄)₂(H₂O)₂] (Hökelek et al., 1997). In (I), the average Zn—O bond length is 2.0935 (12) Å and the Zn atom is displaced out of the least-squares plane of the carboxylate group (O1/C1/O2) by 0.332 (1) Å. The dihedral angle between the planar carboxylate group and the benzene ring A (C2—C7) is 85.51 (12)°, while that between rings A and B (N1/C8—C12) is 44.07 (6)°.

In the crystal structure, intermolecular O—H···O hydrogen bonds (Table 2) link the molecules into infinite chains, in which they may be effective in the stabilization of the structure.

Related literature top

For general backgroud, see: Antolini et al. (1982); Bigoli et al. (1972); Nadzhafov et al. (1981); Shnulin et al. (1981). For related structures, see: Hökelek et al. (1995); (Hökelek & Necefoğlu (1996); Hökelek & Necefoğlu (1997); Hökelek et al. (1997); Hökelek et al. (2007); Hökelek & Necefoğlu (2007); Hökelek et al. (2008).

Experimental top

The title compound was prepared by the reaction of ZnSO₄.H₂O (0.89 g, 5 mmol) in H₂O (20 ml) and DENA (1.78 g, 10 mmol) in H₂O (20 ml) with sodium 2-bromobenzoate (2.23 g, 10 mmol) in H₂O (50 ml). The mixture was filtered and set aside to crystallize at ambient temperature for 3 d, giving colorless single crystals.

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).

Figures top

Fig. 1. The molecular structure of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Primed atoms are generated by the symmetry operator (1 - x, -y, -z).

Diaquabis(2-bromobenzoato-κO)bis(N,N- diethylnicotinamide-κN¹)zinc(II) top

Crystal data top

[Zn(C₇H₄BrO₂)₂(C₁₀H₁₄N₂O)₂(H₂O)₂]	F(000) = 872
M_r = 857.91	D_x = 1.555 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8223 reflections
a = 13.0037 (2) Å	θ = 2.5–28.3°
b = 10.3387 (2) Å	µ = 2.91 mm⁻¹
c = 14.9365 (3) Å	T = 100 K
β = 114.180 (1)°	Block, colorless
V = 1831.90 (6) Å³	0.40 × 0.30 × 0.23 mm
Z = 2

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	4566 independent reflections
Radiation source: fine-focus sealed tube	3769 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.072
ϕ and ω scans	θ_max = 28.3°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −17→17
T_min = 0.368, T_max = 0.517	k = −13→12
16722 measured reflections	l = −15→19

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.073	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ²(F_o²) + (0.0392P)²] where P = (F_o² + 2F_c²)/3
4566 reflections	(Δ/σ)_max < 0.001
232 parameters	Δρ_max = 1.13 e Å⁻³
3 restraints	Δρ_min = −0.53 e Å⁻³

Crystal data top

[Zn(C₇H₄BrO₂)₂(C₁₀H₁₄N₂O)₂(H₂O)₂]	V = 1831.90 (6) Å³
M_r = 857.91	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.0037 (2) Å	µ = 2.91 mm⁻¹
b = 10.3387 (2) Å	T = 100 K
c = 14.9365 (3) Å	0.40 × 0.30 × 0.23 mm
β = 114.180 (1)°

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	4566 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3769 reflections with I > 2σ(I)
T_min = 0.368, T_max = 0.517	R_int = 0.072
16722 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	3 restraints
wR(F²) = 0.073	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	Δρ_max = 1.13 e Å⁻³
4566 reflections	Δρ_min = −0.53 e Å⁻³
232 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	0.5000	0.0000	0.0000	0.00901 (8)
Br1	0.179310 (15)	0.14083 (2)	0.071591 (15)	0.02340 (7)
O1	0.46937 (9)	0.05066 (12)	0.12022 (9)	0.0132 (3)
O2	0.36846 (12)	−0.11814 (12)	0.13299 (11)	0.0250 (3)
H41	0.609 (2)	0.2335 (18)	0.0563 (19)	0.054*
H42	0.621 (2)	0.165 (2)	−0.0200 (14)	0.051 (8)*
O3	0.93267 (10)	−0.11602 (12)	0.39616 (9)	0.0145 (3)
O4	0.61756 (10)	0.15513 (11)	0.03656 (10)	0.0124 (3)
N1	0.64061 (11)	−0.12404 (13)	0.09229 (11)	0.0112 (3)
N2	0.98312 (12)	0.00393 (14)	0.29399 (11)	0.0144 (3)
C1	0.40861 (14)	−0.00793 (16)	0.15495 (13)	0.0126 (4)
C2	0.38508 (14)	0.06826 (17)	0.23084 (14)	0.0136 (4)
C3	0.46126 (15)	0.06990 (19)	0.32819 (14)	0.0195 (4)
H3	0.5255	0.0185	0.3482	0.023*
C4	0.44314 (17)	0.14731 (19)	0.39657 (16)	0.0239 (5)
H4	0.4946	0.1468	0.4619	0.029*
C5	0.34836 (17)	0.22509 (19)	0.36715 (15)	0.0239 (4)
H5	0.3375	0.2789	0.4124	0.029*
C6	0.26950 (16)	0.22321 (19)	0.27050 (15)	0.0221 (4)
H6	0.2050	0.2742	0.2507	0.026*
C7	0.28856 (15)	0.14373 (17)	0.20386 (15)	0.0166 (4)
C8	0.64246 (14)	−0.25181 (17)	0.07850 (14)	0.0136 (4)
H8	0.5822	−0.2893	0.0269	0.016*
C9	0.73019 (14)	−0.33078 (18)	0.13771 (14)	0.0145 (4)
H9	0.7280	−0.4193	0.1260	0.017*
C10	0.82084 (13)	−0.27652 (17)	0.21415 (13)	0.0129 (4)
H10	0.8799	−0.3276	0.2559	0.016*
C11	0.82133 (14)	−0.14260 (16)	0.22691 (13)	0.0118 (4)
C12	0.72970 (13)	−0.07125 (17)	0.16538 (13)	0.0120 (3)
H12	0.7299	0.0176	0.1752	0.014*
C13	0.91743 (13)	−0.08274 (16)	0.31181 (13)	0.0113 (3)
C14	1.08066 (14)	0.05572 (17)	0.37778 (14)	0.0157 (4)
H14A	1.0630	0.0598	0.4348	0.019*
H14B	1.0963	0.1429	0.3629	0.019*
C15	1.18465 (15)	−0.0281 (2)	0.40103 (15)	0.0227 (4)
H15A	1.2466	0.0073	0.4564	0.034*
H15B	1.2035	−0.0302	0.3452	0.034*
H15C	1.1694	−0.1144	0.4161	0.034*
C16	0.97478 (16)	0.0395 (2)	0.19646 (15)	0.0239 (4)
H16A	0.9254	−0.0213	0.1487	0.029*
H16B	1.0488	0.0327	0.1956	0.029*
C17	0.93007 (18)	0.1756 (2)	0.16644 (18)	0.0343 (6)
H17A	0.9327	0.1967	0.1048	0.051*
H17B	0.9756	0.2359	0.2156	0.051*
H17C	0.8536	0.1804	0.1599	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.00857 (13)	0.01000 (15)	0.00909 (15)	−0.00008 (10)	0.00427 (11)	−0.00017 (11)
Br1	0.02151 (11)	0.02979 (13)	0.01957 (12)	0.00542 (8)	0.00908 (9)	0.00255 (8)
O1	0.0148 (6)	0.0149 (6)	0.0135 (6)	−0.0024 (5)	0.0094 (5)	−0.0013 (5)
O2	0.0432 (9)	0.0140 (7)	0.0321 (9)	−0.0092 (6)	0.0300 (7)	−0.0064 (6)
O3	0.0162 (6)	0.0137 (6)	0.0112 (7)	−0.0013 (5)	0.0031 (5)	0.0008 (5)
O4	0.0138 (6)	0.0103 (6)	0.0138 (7)	−0.0008 (5)	0.0064 (5)	−0.0003 (5)
N1	0.0114 (7)	0.0109 (7)	0.0119 (8)	0.0006 (5)	0.0054 (6)	0.0000 (6)
N2	0.0141 (7)	0.0173 (8)	0.0114 (8)	−0.0032 (6)	0.0048 (6)	0.0002 (6)
C1	0.0138 (8)	0.0127 (9)	0.0131 (9)	0.0033 (6)	0.0074 (7)	0.0011 (7)
C2	0.0171 (8)	0.0109 (9)	0.0183 (9)	−0.0041 (7)	0.0128 (7)	−0.0020 (7)
C3	0.0174 (9)	0.0224 (11)	0.0205 (10)	−0.0018 (7)	0.0098 (8)	−0.0032 (8)
C4	0.0260 (10)	0.0318 (12)	0.0173 (10)	−0.0096 (8)	0.0123 (9)	−0.0067 (9)
C5	0.0349 (11)	0.0232 (11)	0.0243 (11)	−0.0068 (8)	0.0229 (9)	−0.0092 (9)
C6	0.0267 (10)	0.0206 (10)	0.0276 (11)	0.0011 (8)	0.0200 (9)	−0.0029 (9)
C7	0.0191 (9)	0.0187 (10)	0.0149 (9)	−0.0017 (7)	0.0102 (8)	0.0000 (8)
C8	0.0114 (8)	0.0157 (9)	0.0135 (9)	−0.0022 (6)	0.0050 (7)	−0.0013 (7)
C9	0.0171 (8)	0.0099 (8)	0.0172 (10)	0.0005 (7)	0.0076 (7)	0.0000 (7)
C10	0.0125 (8)	0.0143 (9)	0.0123 (9)	0.0026 (6)	0.0054 (7)	0.0023 (7)
C11	0.0119 (8)	0.0138 (9)	0.0107 (9)	−0.0016 (6)	0.0056 (7)	−0.0002 (7)
C12	0.0142 (8)	0.0114 (9)	0.0114 (9)	−0.0001 (6)	0.0063 (7)	−0.0002 (7)
C13	0.0097 (8)	0.0090 (8)	0.0132 (9)	0.0033 (6)	0.0026 (7)	0.0006 (7)
C14	0.0166 (8)	0.0152 (9)	0.0135 (9)	−0.0051 (7)	0.0043 (7)	−0.0023 (8)
C15	0.0175 (9)	0.0282 (11)	0.0213 (11)	−0.0017 (8)	0.0069 (8)	0.0031 (9)
C16	0.0200 (9)	0.0365 (12)	0.0147 (10)	−0.0114 (8)	0.0066 (8)	0.0017 (9)
C17	0.0270 (11)	0.0413 (14)	0.0281 (13)	−0.0069 (10)	0.0046 (10)	0.0191 (11)

Geometric parameters (Å, º) top

Zn1—O1ⁱ	2.0600 (12)	C6—H6	0.9300
Zn1—O1	2.0600 (12)	C7—C2	1.390 (2)
Zn1—O4	2.1269 (12)	C7—C6	1.389 (3)
Zn1—N1	2.1962 (14)	C8—C9	1.387 (2)
Zn1—O4ⁱ	2.1269 (12)	C8—H8	0.9300
Zn1—N1ⁱ	2.1962 (14)	C9—H9	0.9300
Br1—C7	1.903 (2)	C10—C9	1.380 (2)
O1—C1	1.263 (2)	C10—H10	0.9300
O2—C1	1.240 (2)	C11—C10	1.397 (2)
O3—C13	1.241 (2)	C11—C12	1.383 (2)
O4—Zn1	2.1269 (12)	C11—C13	1.502 (2)
O4—H41	0.885 (16)	C12—H12	0.9300
O4—H42	0.869 (15)	C13—N2	1.338 (2)
N1—Zn1	2.1962 (14)	C14—C15	1.522 (2)
N1—C8	1.339 (2)	C14—H14A	0.9700
N1—C12	1.340 (2)	C14—H14B	0.9700
N2—C14	1.470 (2)	C15—H15A	0.9600
N2—C16	1.463 (2)	C15—H15B	0.9600
C2—C1	1.511 (2)	C15—H15C	0.9600
C2—C3	1.384 (3)	C16—C17	1.518 (3)
C3—H3	0.9300	C16—H16A	0.9700
C4—C3	1.391 (3)	C16—H16B	0.9700
C4—C5	1.384 (3)	C17—H17A	0.9600
C4—H4	0.9300	C17—H17B	0.9600
C5—H5	0.9300	C17—H17C	0.9600
C6—C5	1.387 (3)

O1ⁱ—Zn1—O1	180.00 (5)	C6—C7—Br1	118.47 (14)
O1ⁱ—Zn1—O4ⁱ	87.69 (5)	C6—C7—C2	121.96 (19)
O1—Zn1—O4ⁱ	92.31 (5)	N1—C8—C9	123.00 (16)
O1ⁱ—Zn1—O4	92.31 (5)	N1—C8—H8	118.5
O1—Zn1—O4	87.69 (5)	C9—C8—H8	118.5
O4ⁱ—Zn1—O4	180.00 (7)	C8—C9—H9	120.4
O1ⁱ—Zn1—N1ⁱ	90.56 (5)	C10—C9—C8	119.27 (17)
O1—Zn1—N1ⁱ	89.44 (5)	C10—C9—H9	120.4
O1ⁱ—Zn1—N1	89.44 (5)	C9—C10—C11	118.05 (16)
O1—Zn1—N1	90.56 (5)	C9—C10—H10	121.0
O4ⁱ—Zn1—N1ⁱ	87.31 (5)	C11—C10—H10	121.0
O4—Zn1—N1ⁱ	92.69 (5)	C10—C11—C13	118.64 (15)
O4ⁱ—Zn1—N1	92.69 (5)	C12—C11—C10	118.91 (16)
O4—Zn1—N1	87.31 (5)	C12—C11—C13	122.28 (15)
N1ⁱ—Zn1—N1	180.00 (14)	N1—C12—C11	123.12 (16)
C1—O1—Zn1	127.79 (11)	N1—C12—H12	118.4
Zn1—O4—H41	126.9 (17)	C11—C12—H12	118.4
Zn1—O4—H42	98.8 (17)	O3—C13—N2	122.56 (16)
H42—O4—H41	106 (2)	O3—C13—C11	118.34 (15)
C8—N1—Zn1	122.85 (11)	N2—C13—C11	119.10 (16)
C8—N1—C12	117.59 (15)	N2—C14—C15	111.29 (15)
C12—N1—Zn1	119.56 (11)	N2—C14—H14A	109.4
C13—N2—C14	118.24 (15)	N2—C14—H14B	109.4
C13—N2—C16	125.02 (15)	C15—C14—H14A	109.4
C16—N2—C14	116.24 (14)	C15—C14—H14B	109.4
O1—C1—C2	114.26 (15)	H14A—C14—H14B	108.0
O2—C1—O1	126.75 (16)	C14—C15—H15A	109.5
O2—C1—C2	118.99 (15)	C14—C15—H15B	109.5
C3—C2—C1	121.12 (16)	C14—C15—H15C	109.5
C3—C2—C7	118.06 (17)	H15A—C15—H15B	109.5
C7—C2—C1	120.76 (17)	H15A—C15—H15C	109.5
C2—C3—C4	120.98 (18)	H15B—C15—H15C	109.5
C2—C3—H3	119.5	N2—C16—C17	112.98 (18)
C4—C3—H3	119.5	N2—C16—H16A	109.0
C3—C4—H4	120.1	N2—C16—H16B	109.0
C5—C4—C3	119.8 (2)	C17—C16—H16A	109.0
C5—C4—H4	120.1	C17—C16—H16B	109.0
C4—C5—C6	120.33 (18)	H16A—C16—H16B	107.8
C4—C5—H5	119.8	C16—C17—H17A	109.5
C6—C5—H5	119.8	C16—C17—H17B	109.5
C5—C6—C7	118.77 (18)	C16—C17—H17C	109.5
C5—C6—H6	120.6	H17A—C17—H17B	109.5
C7—C6—H6	120.6	H17A—C17—H17C	109.5
C2—C7—Br1	119.57 (14)	H17B—C17—H17C	109.5

O4ⁱ—Zn1—O1—C1	5.89 (14)	C1—C2—C3—C4	175.41 (16)
O4—Zn1—O1—C1	−174.11 (14)	C7—C2—C3—C4	−1.6 (3)
N1ⁱ—Zn1—O1—C1	93.18 (14)	C5—C4—C3—C2	−0.7 (3)
N1—Zn1—O1—C1	−86.82 (14)	C3—C4—C5—C6	2.1 (3)
Zn1—O1—C1—O2	11.8 (3)	C7—C6—C5—C4	−1.1 (3)
Zn1—O1—C1—C2	−168.33 (11)	Br1—C7—C2—C1	4.8 (2)
C8—N1—Zn1—O1ⁱ	−61.43 (14)	Br1—C7—C2—C3	−178.23 (13)
C8—N1—Zn1—O1	118.57 (14)	C6—C7—C2—C1	−174.44 (16)
C8—N1—Zn1—O4ⁱ	26.23 (14)	C6—C7—C2—C3	2.6 (3)
C8—N1—Zn1—O4	−153.77 (14)	Br1—C7—C6—C5	179.54 (14)
C12—N1—Zn1—O1ⁱ	117.92 (13)	C2—C7—C6—C5	−1.2 (3)
C12—N1—Zn1—O1	−62.08 (13)	N1—C8—C9—C10	−0.6 (3)
C12—N1—Zn1—O4ⁱ	−154.42 (13)	C11—C10—C9—C8	−1.6 (3)
C12—N1—Zn1—O4	25.58 (13)	C12—C11—C10—C9	2.5 (3)
Zn1—N1—C8—C9	−178.82 (13)	C13—C11—C10—C9	177.93 (16)
C12—N1—C8—C9	1.8 (3)	C10—C11—C12—N1	−1.3 (3)
Zn1—N1—C12—C11	179.78 (13)	C13—C11—C12—N1	−176.57 (16)
C8—N1—C12—C11	−0.8 (2)	C10—C11—C13—O3	−61.1 (2)
C13—N2—C14—C15	88.7 (2)	C10—C11—C13—N2	118.94 (18)
C16—N2—C14—C15	−83.6 (2)	C12—C11—C13—O3	114.20 (19)
C13—N2—C16—C17	109.9 (2)	C12—C11—C13—N2	−65.8 (2)
C14—N2—C16—C17	−78.4 (2)	O3—C13—N2—C14	3.5 (2)
C3—C2—C1—O1	−83.7 (2)	O3—C13—N2—C16	175.04 (17)
C3—C2—C1—O2	96.2 (2)	C11—C13—N2—C14	−176.49 (14)
C7—C2—C1—O1	93.2 (2)	C11—C13—N2—C16	−4.9 (3)
C7—C2—C1—O2	−86.9 (2)

Symmetry code: (i) −x+1, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H41···O3ⁱⁱ	0.88 (2)	1.88 (2)	2.7518 (18)	168 (3)
O4—H42···O2ⁱ	0.87 (2)	1.81 (2)	2.640 (2)	158 (2)

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

Experimental details

Crystal data
Chemical formula	[Zn(C₇H₄BrO₂)₂(C₁₀H₁₄N₂O)₂(H₂O)₂]
M_r	857.91
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	13.0037 (2), 10.3387 (2), 14.9365 (3)
β (°)	114.180 (1)
V (Å³)	1831.90 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.91
Crystal size (mm)	0.40 × 0.30 × 0.23

Data collection
Diffractometer	Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.368, 0.517
No. of measured, independent and observed [I > 2σ(I)] reflections	16722, 4566, 3769
R_int	0.072
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.073, 0.98
No. of reflections	4566
No. of parameters	232
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.13, −0.53

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

Selected bond lengths (Å) top

Zn1—O1	2.0600 (12)	Zn1—N1	2.1962 (14)
Zn1—O4	2.1269 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H41···O3ⁱ	0.88 (2)	1.88 (2)	2.7518 (18)	168 (3)
O4—H42···O2ⁱⁱ	0.87 (2)	1.81 (2)	2.640 (2)	158 (2)

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

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.

References

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