Diaqua­bis(2-bromo­benzoato-κO)bis­(nicotinamide-κN1)zinc(II)

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

doi:10.1107/S1600536809015645

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Pages m607-m608

doi:10.1107/S1600536809015645

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Diaquabis(2-bromobenzoato-κO)bis(nicotinamide-κN¹)zinc(II)

Tuncer Hökelek,^a ^* Hakan Dal,^b Barış Tercan,^c F. Elif Özbek ^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 24 April 2009; accepted 27 April 2009; online 30 April 2009)

The title Zn^II complex, [Zn(C₇H₄BrO₂)₂(C₆H₆N₂O)₂(H₂O)₂], is centrosymmetric with the Zn atom on an inversion center. The molecule contains two 2-bromobenzoate (BB) and two nicotinamide (NA) ligands and two coordinated water molecules, all ligands being monodentate. 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 NA ligands in the axial positions. The dihedral angle between the carboxyl group and the adjacent benzene ring is 31.14 (12)°, while the pyridine and benzene rings are oriented at a dihedral angle of 83.54 (5)°. In the crystal structure, O—H⋯O and N—H⋯O hydrogen bonds link the molecules into infinite chains. A weak C—H⋯π interaction is also present.

Related literature

For general backgroud to the properties of transition metal complexes with biochemically active ligands, see: Antolini et al. (1982 ); Bigoli et al. (1972 ); Krishnamachari (1974 ); 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(C₆H₆N₂O)₂(H₂O)₂]
M_r = 745.68
Monoclinic, P 2₁ /n
a = 7.9111 (2) Å
b = 18.1604 (4) Å
c = 9.8345 (3) Å
β = 106.346 (1)°
V = 1355.80 (6) Å³
Z = 2
Mo Kα radiation
μ = 3.91 mm⁻¹
T = 100 K
0.43 × 0.33 × 0.24 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffctometer diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.230, T_max = 0.393
12839 measured reflections
3416 independent reflections
2948 reflections with I > 2σ(I)
R_int = 0.081

Refinement

R[F² > 2σ(F²)] = 0.026
wR(F²) = 0.065
S = 1.06
3416 reflections
203 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.77 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Table 1
Selected bond lengths (Å)

Zn1—O1	2.1182 (13)
Zn1—O4	2.1647 (12)
Zn1—N1	2.1124 (14)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H21⋯O2ⁱ	0.83 (2)	2.10 (2)	2.870 (2)	155 (2)
O4—H41⋯O2ⁱⁱ	0.83 (3)	1.84 (3)	2.6339 (19)	159 (3)
C11—H11⋯Cg1ⁱⁱⁱ	0.93	2.87	3.600 (3)	136
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) -x+2, -y+1, -z+2; (iii) -x+1, -y, -z. Cg1 is the centroid of the C2–C7 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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809015645/xu2517sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809015645/xu2517Isup2.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). Nicotinamide (NA) is one form of niacin and a deficiency of this vitamin leads to loss of copper from the body, known as pellagra disease. Victims of pellagra show unusually high serum and urinary copper levels (Krishnamachari, 1974). On the other hand, 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 nicotinamide (NA) 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 NA 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 NA ligands (N1, N1') in the axial positions (Table 1 and Fig. 1).

The near equality of the C1—O1 [1.267 (2) Å] and C1—O2 [1.256 (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], (II) (Hökelek et al., 2008), 1.265 (6) and 1.275 (6) Å in [Mn(C₉H₁₀NO₂)₂(H₂O)₄].2(H₂O), (III) (Hökelek & Necefoğlu, 2007), 1.260 (4) and 1.252 (4) Å in [Zn(DENA)₂(C₇H₄FO₂)₂(H₂O)₂],(IV) (Hökelek et al., 2007), 1.259 (9) and 1.273 (9) Å in Cu₂(DENA)₂(C₆H₅COO)₄, (V) (Hökelek et al., 1995), 1.279 (4) and 1.246 (4) Å in [Zn₂(DENA)₂(C₇H₅O₃)₄].2H₂O, (VI) (Hökelek & Necefoğlu, 1996), 1.251 (6) and 1.254 (7) Å in [Co(DENA)₂(C₇H₅O₃)₂(H₂O)₂], (VII) (Hökelek & Necefoğlu, 1997) and 1.278 (3) and 1.246 (3) Å in [Cu(DENA)₂(C₇H₄NO₄)₂(H₂O)₂], (VIII) (Hökelek et al., 1997). In (I), the average Zn—O bond length is 2.1415 (13) Å and the Zn atom is displaced out of the least-squares plane of the carboxylate group (O1/C1/O2) by -0.676 (1) Å. The dihedral angle between the planar carboxylate group and the benzene ring A (C2—C7) is 31.14 (12)°, while that between rings A and B (N1/C8—C12) is 83.54 (5)°.

In the crystal structure, intermolecular O—H···O and N—H···O hydrogen bonds (Table 2) link the molecules into infinite chains, in which they may be effective in the stabilization of the structure. There also exists a weak C–H···π interaction (Table 2).

Related literature top

For general backgroud to the properties of transition metal complexes with biochemically active ligands, see: Antolini et al. (1982); Bigoli et al. (1972); Krishnamachari (1974); Nadzhafov et al. (1981); Shnulin et al. (1981). For related structures, see: Hökelek et al. (1995, 1997, 2007, 2008); Hökelek & Necefoğlu (1996, 1997, 2007). Cg1 is the centroid of the C2–C7 ring.

Experimental top

The title compound was prepared by the reaction of ZnSO₄.H₂O (0.89 g, 5 mmol) in H₂O (20 ml) and NA (1.22 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 (2 - x, 1 -y, 2 -z).

Diaquabis(2-bromobenzoato-κO)bis(nicotinamide-κN¹)zinc(II) top

Crystal data top

[Zn(C₇H₄BrO₂)₂(C₆H₆N₂O)₂(H₂O)₂]	F(000) = 744
M_r = 745.68	D_x = 1.827 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7038 reflections
a = 7.9111 (2) Å	θ = 2.4–28.4°
b = 18.1604 (4) Å	µ = 3.91 mm⁻¹
c = 9.8345 (3) Å	T = 100 K
β = 106.346 (1)°	Block, colorless
V = 1355.80 (6) Å³	0.43 × 0.33 × 0.24 mm
Z = 2

Data collection top

Bruker Kappa APEXII CCD area-detector diffctometer diffractometer	3416 independent reflections
Radiation source: fine-focus sealed tube	2948 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.081
ϕ and ω scans	θ_max = 28.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→10
T_min = 0.230, T_max = 0.393	k = −24→23
12839 measured reflections	l = −13→13

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.065	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0306P)²] where P = (F_o² + 2F_c²)/3
3416 reflections	(Δ/σ)_max = 0.001
203 parameters	Δρ_max = 0.77 e Å⁻³
1 restraint	Δρ_min = −0.51 e Å⁻³

Crystal data top

[Zn(C₇H₄BrO₂)₂(C₆H₆N₂O)₂(H₂O)₂]	V = 1355.80 (6) Å³
M_r = 745.68	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.9111 (2) Å	µ = 3.91 mm⁻¹
b = 18.1604 (4) Å	T = 100 K
c = 9.8345 (3) Å	0.43 × 0.33 × 0.24 mm
β = 106.346 (1)°

Data collection top

Bruker Kappa APEXII CCD area-detector diffctometer diffractometer	3416 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2948 reflections with I > 2σ(I)
T_min = 0.230, T_max = 0.393	R_int = 0.081
12839 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	1 restraint
wR(F²) = 0.065	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.77 e Å⁻³
3416 reflections	Δρ_min = −0.51 e Å⁻³
203 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
Br1	0.90022 (2)	0.210886 (11)	0.671443 (19)	0.02134 (7)
Zn1	1.0000	0.5000	1.0000	0.01096 (8)
O1	1.11803 (16)	0.40204 (7)	0.95347 (12)	0.0142 (3)
O2	0.89388 (16)	0.36730 (8)	0.77083 (12)	0.0163 (3)
O3	1.45377 (17)	0.51058 (8)	0.67688 (12)	0.0186 (3)
O4	1.26223 (16)	0.54361 (8)	1.09090 (12)	0.0145 (3)
H41	1.238 (4)	0.5757 (17)	1.143 (3)	0.048 (9)*
H42	1.343 (3)	0.5165 (13)	1.146 (2)	0.030 (6)*
N1	1.00804 (19)	0.54424 (9)	0.80326 (14)	0.0126 (3)
N2	1.3585 (2)	0.58056 (11)	0.48109 (16)	0.0193 (4)
H21	1.272 (3)	0.6009 (14)	0.427 (2)	0.031 (7)*
H22	1.447 (4)	0.5666 (15)	0.452 (3)	0.031 (7)*
C1	1.0529 (2)	0.36488 (10)	0.84198 (16)	0.0125 (3)
C2	1.1764 (2)	0.31803 (10)	0.78680 (16)	0.0127 (3)
C3	1.3510 (2)	0.34108 (11)	0.81090 (17)	0.0149 (4)
H3	1.3907	0.3815	0.8692	0.018*
C4	1.4661 (2)	0.30548 (11)	0.75047 (18)	0.0177 (4)
H4	1.5816	0.3219	0.7683	0.021*
C5	1.4089 (2)	0.24503 (12)	0.66281 (17)	0.0171 (4)
H5	1.4850	0.2220	0.6193	0.021*
C6	1.2392 (2)	0.21919 (11)	0.64049 (17)	0.0157 (4)
H6	1.2014	0.1780	0.5838	0.019*
C7	1.1250 (2)	0.25506 (11)	0.70332 (16)	0.0133 (4)
C8	1.1546 (2)	0.53766 (10)	0.76238 (16)	0.0133 (4)
H8	1.2498	0.5127	0.8216	0.016*
C9	1.1722 (2)	0.56605 (10)	0.63648 (16)	0.0126 (3)
C10	1.0301 (2)	0.60450 (11)	0.54960 (17)	0.0162 (4)
H10	1.0381	0.6251	0.4650	0.019*
C11	0.8777 (2)	0.61176 (11)	0.58996 (17)	0.0171 (4)
H11	0.7815	0.6372	0.5333	0.020*
C12	0.8705 (2)	0.58033 (11)	0.71677 (17)	0.0147 (4)
H12	0.7669	0.5843	0.7431	0.018*
C13	1.3397 (2)	0.55091 (11)	0.59974 (17)	0.0147 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.01423 (10)	0.02129 (13)	0.02759 (11)	−0.00591 (7)	0.00440 (7)	−0.00471 (7)
Zn1	0.00902 (14)	0.01609 (17)	0.00751 (12)	0.00017 (10)	0.00189 (10)	0.00020 (10)
O1	0.0127 (6)	0.0182 (7)	0.0104 (5)	0.0032 (5)	0.0010 (4)	−0.0004 (5)
O2	0.0098 (6)	0.0249 (8)	0.0128 (5)	0.0021 (5)	0.0010 (5)	−0.0018 (5)
O3	0.0129 (6)	0.0297 (9)	0.0133 (6)	0.0062 (6)	0.0040 (5)	0.0051 (5)
O4	0.0102 (6)	0.0197 (8)	0.0127 (6)	0.0009 (5)	0.0019 (5)	−0.0007 (5)
N1	0.0102 (7)	0.0158 (8)	0.0112 (6)	0.0000 (6)	0.0020 (5)	−0.0002 (5)
N2	0.0131 (8)	0.0325 (10)	0.0139 (7)	0.0068 (7)	0.0064 (6)	0.0069 (7)
C1	0.0120 (8)	0.0154 (9)	0.0099 (7)	−0.0004 (7)	0.0029 (6)	0.0031 (6)
C2	0.0135 (8)	0.0145 (9)	0.0091 (7)	0.0019 (7)	0.0018 (6)	0.0018 (6)
C3	0.0128 (8)	0.0163 (10)	0.0139 (7)	0.0002 (7)	0.0011 (6)	−0.0006 (7)
C4	0.0114 (8)	0.0231 (11)	0.0185 (8)	−0.0010 (7)	0.0038 (7)	0.0016 (7)
C5	0.0169 (9)	0.0211 (11)	0.0149 (8)	0.0056 (7)	0.0069 (7)	0.0030 (7)
C6	0.0176 (9)	0.0162 (10)	0.0122 (7)	0.0016 (7)	0.0023 (7)	−0.0007 (6)
C7	0.0111 (8)	0.0168 (10)	0.0107 (7)	−0.0008 (7)	0.0007 (6)	0.0016 (6)
C8	0.0119 (8)	0.0154 (10)	0.0115 (7)	0.0013 (7)	0.0013 (6)	0.0004 (6)
C9	0.0115 (8)	0.0155 (10)	0.0109 (7)	0.0003 (6)	0.0033 (6)	−0.0008 (6)
C10	0.0146 (8)	0.0238 (11)	0.0103 (7)	0.0025 (7)	0.0038 (6)	0.0042 (7)
C11	0.0132 (8)	0.0216 (11)	0.0142 (7)	0.0048 (7)	0.0003 (7)	0.0042 (7)
C12	0.0122 (8)	0.0180 (10)	0.0141 (7)	0.0018 (7)	0.0038 (6)	0.0001 (7)
C13	0.0120 (8)	0.0199 (10)	0.0119 (7)	0.0002 (7)	0.0031 (6)	−0.0016 (6)

Geometric parameters (Å, º) top

Br1—C7	1.8950 (18)	C4—C3	1.380 (3)
Zn1—O1ⁱ	2.1182 (13)	C4—H4	0.9300
Zn1—O1	2.1182 (13)	C5—C4	1.390 (3)
Zn1—O4ⁱ	2.1647 (12)	C5—C6	1.380 (3)
Zn1—O4	2.1647 (12)	C5—H5	0.9300
Zn1—N1	2.1124 (14)	C6—H6	0.9300
Zn1—N1ⁱ	2.1124 (14)	C7—C2	1.400 (3)
O1—C1	1.267 (2)	C7—C6	1.392 (3)
O2—C1	1.256 (2)	C8—C9	1.384 (2)
O3—C13	1.242 (2)	C8—H8	0.9300
O4—H41	0.83 (3)	C10—C9	1.393 (2)
O4—H42	0.869 (16)	C10—C11	1.378 (3)
N1—C8	1.335 (2)	C10—H10	0.9300
N1—C12	1.347 (2)	C11—C12	1.387 (3)
N2—H21	0.83 (2)	C11—H11	0.9300
N2—H22	0.86 (3)	C12—H12	0.9300
C1—C2	1.507 (3)	C13—N2	1.331 (2)
C2—C3	1.399 (2)	C13—C9	1.494 (2)
C3—H3	0.9300

O1ⁱ—Zn1—O1	180.0	C4—C3—C2	121.78 (17)
O1—Zn1—O4	88.11 (5)	C4—C3—H3	119.1
O1ⁱ—Zn1—O4	91.89 (5)	C3—C4—C5	119.88 (17)
O1—Zn1—O4ⁱ	91.89 (5)	C3—C4—H4	120.1
O1ⁱ—Zn1—O4ⁱ	88.11 (5)	C5—C4—H4	120.1
O4ⁱ—Zn1—O4	180.0	C4—C5—H5	120.0
N1—Zn1—O1	89.59 (5)	C6—C5—C4	119.94 (17)
N1ⁱ—Zn1—O1	90.41 (5)	C6—C5—H5	120.0
N1—Zn1—O1ⁱ	90.41 (5)	C5—C6—C7	119.62 (17)
N1ⁱ—Zn1—O1ⁱ	89.59 (5)	C5—C6—H6	120.2
N1—Zn1—O4	88.09 (5)	C7—C6—H6	120.2
N1ⁱ—Zn1—O4	91.91 (5)	C2—C7—Br1	123.15 (14)
N1—Zn1—O4ⁱ	91.91 (5)	C6—C7—Br1	115.13 (14)
N1ⁱ—Zn1—O4ⁱ	88.09 (5)	C6—C7—C2	121.70 (16)
N1—Zn1—N1ⁱ	180.000 (1)	N1—C8—C9	123.40 (15)
Zn1—O4—H42	120.3 (18)	N1—C8—H8	118.3
Zn1—O4—H41	99 (2)	C9—C8—H8	118.3
H42—O4—H41	106 (2)	C8—C9—C10	117.95 (17)
C1—O1—Zn1	122.52 (11)	C8—C9—C13	117.85 (15)
C8—N1—Zn1	119.62 (11)	C10—C9—C13	124.15 (15)
C8—N1—C12	117.94 (15)	C9—C10—H10	120.3
C12—N1—Zn1	122.42 (12)	C11—C10—C9	119.46 (16)
C13—N2—H21	117.7 (18)	C11—C10—H10	120.3
C13—N2—H22	118.2 (17)	C10—C11—C12	118.67 (16)
H21—N2—H22	121 (2)	C10—C11—H11	120.7
O1—C1—C2	117.73 (15)	C12—C11—H11	120.7
O2—C1—O1	124.27 (17)	N1—C12—C11	122.55 (17)
O2—C1—C2	117.91 (15)	N1—C12—H12	118.7
C3—C2—C1	118.66 (17)	C11—C12—H12	118.7
C3—C2—C7	116.98 (16)	O3—C13—N2	122.19 (18)
C7—C2—C1	124.19 (16)	O3—C13—C9	120.18 (16)
C2—C3—H3	119.1	N2—C13—C9	117.61 (16)

O4ⁱ—Zn1—O1—C1	36.30 (14)	C1—C2—C3—C4	−172.78 (16)
O4—Zn1—O1—C1	−143.70 (14)	C7—C2—C3—C4	2.7 (3)
N1—Zn1—O1—C1	−55.59 (14)	C5—C4—C3—C2	0.1 (3)
N1ⁱ—Zn1—O1—C1	124.41 (14)	C6—C5—C4—C3	−2.3 (3)
O1ⁱ—Zn1—N1—C8	134.53 (14)	C4—C5—C6—C7	1.6 (3)
O1—Zn1—N1—C8	−45.47 (14)	Br1—C7—C2—C1	−10.0 (2)
O1ⁱ—Zn1—N1—C12	−44.44 (14)	Br1—C7—C2—C3	174.80 (12)
O1—Zn1—N1—C12	135.56 (14)	C6—C7—C2—C1	171.77 (16)
O4ⁱ—Zn1—N1—C8	−137.35 (14)	C6—C7—C2—C3	−3.4 (2)
O4—Zn1—N1—C8	42.65 (14)	Br1—C7—C6—C5	−177.00 (13)
O4ⁱ—Zn1—N1—C12	43.68 (14)	C2—C7—C6—C5	1.4 (3)
O4—Zn1—N1—C12	−136.32 (14)	N1—C8—C9—C10	1.1 (3)
Zn1—O1—C1—O2	−22.3 (2)	N1—C8—C9—C13	−176.47 (16)
Zn1—O1—C1—C2	154.15 (12)	C11—C10—C9—C8	−1.2 (3)
Zn1—N1—C8—C9	−178.88 (14)	C11—C10—C9—C13	176.27 (18)
C12—N1—C8—C9	0.1 (3)	C9—C10—C11—C12	0.0 (3)
Zn1—N1—C12—C11	177.59 (15)	C10—C11—C12—N1	1.3 (3)
C8—N1—C12—C11	−1.4 (3)	O3—C13—C9—C8	4.0 (3)
O1—C1—C2—C3	−30.2 (2)	O3—C13—C9—C10	−173.46 (18)
O1—C1—C2—C7	154.63 (17)	N2—C13—C9—C8	−177.63 (18)
O2—C1—C2—C3	146.41 (17)	N2—C13—C9—C10	4.9 (3)
O2—C1—C2—C7	−28.7 (3)

Symmetry code: (i) −x+2, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H21···O2ⁱⁱ	0.83 (2)	2.10 (2)	2.870 (2)	155 (2)
O4—H41···O2ⁱ	0.83 (3)	1.84 (3)	2.6339 (19)	159 (3)
C11—H11···Cg1ⁱⁱⁱ	0.93	2.87	3.600 (3)	136

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

Experimental details

Crystal data
Chemical formula	[Zn(C₇H₄BrO₂)₂(C₆H₆N₂O)₂(H₂O)₂]
M_r	745.68
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	7.9111 (2), 18.1604 (4), 9.8345 (3)
β (°)	106.346 (1)
V (Å³)	1355.80 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	3.91
Crystal size (mm)	0.43 × 0.33 × 0.24

Data collection
Diffractometer	Bruker Kappa APEXII CCD area-detector diffctometer diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.230, 0.393
No. of measured, independent and observed [I > 2σ(I)] reflections	12839, 3416, 2948
R_int	0.081
(sin θ/λ)_max (Å⁻¹)	0.671

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.065, 1.06
No. of reflections	3416
No. of parameters	203
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.77, −0.51

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	2.1182 (13)	Zn1—N1	2.1124 (14)
Zn1—O4	2.1647 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H21···O2ⁱ	0.83 (2)	2.10 (2)	2.870 (2)	155 (2)
O4—H41···O2ⁱⁱ	0.83 (3)	1.84 (3)	2.6339 (19)	159 (3)
C11—H11···Cg1ⁱⁱⁱ	0.93	2.87	3.600 (3)	136

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

References

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