Diaqua-bis(2-bromo-benzoato-κO)bis-(N,N-diethyl-nicotinamide-κN)zinc(II).

In the centrosymmetric title complex, [Zn(C(7)H(4)BrO(2))(2)(C(10)H(14)N(2)O)(2)(H(2)O)(2)], the Zn(II) atom is located on an inversion center. The asymmetric unit contains one 2-bromo-benzoate (BB), one diethyl-nicotinamide (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 octa-hedral 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 mol-ecules 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 = 857.91

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.073

S = 0.98

4566 reflections

232 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.13 e Å−3

Δρmin = −0.53 e Å−3

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 ▶).

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Zn(C7H4BrO2)2(C10H14N2O)2(H2O)2]	F(000) = 872
Mr = 857.91	Dx = 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

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

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(Fo2) + (0.0392P)2] where P = (Fo2 + 2Fc2)/3
4566 reflections	(Δ/σ)max < 0.001
232 parameters	Δρmax = 1.13 e Å−3
3 restraints	Δρmin = −0.53 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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)

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) ; (ii) .