Literature DB >> 21201650

Diaquabis(4-bromo-benzoato-κO)-bis(N,N'-diethyl-nicotinamide-κN)zinc(II).

Aslı Oztürk, Tuncer Hökelek, Fureya Elif Ozbek, Hacali Necefoğlu.   

Abstract

The title compound, [Zn(C(7)H(4)BrO(2))(2)(C(10)H(14)N(2)O)(2)(H(2)O)(2)], is a monomeric complex with the Zn(II) atom lying on an inversion center. It contains two 4-bromo-benzoate, two diethyl-nicotinamide ligands and two water mol-ecules, all of which are monodentate. The four O atoms in the equatorial plane around the Zn atom form a slightly distorted square-planar arrangement, while the distorted octa-hedral geometry is completed by two N atoms in the axial positions. The methyl group of one of the ethyl groups is disordered over two positions, with occupancies of ca 0.65 and 0.35. The two aromatic rings are oriented at an angle of 77.22 (14)°. In the crystal structure, O-H⋯O hydrogen bonds link the mol-ecules into chains along the a axis.

Entities:  

Year:  2008        PMID： 21201650      PMCID： PMC2960695          DOI： 10.1107/S1600536808027074

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For general background, see: Antolini et al. (1982 ▶); Nadzhafov et al. (1981 ▶). For related literature, see: Clegg et al. (1986a ▶,b ▶); Capilla & Aranda (1979 ▶); Usubaliev et al. (1992 ▶); Hökelek et al. (1995 ▶, 1997 ▶, 2007 ▶); Hökelek & Necefoğlu (1996 ▶, 1997 ▶); Necefoğlu et al. (2002 ▶).

Experimental

Crystal data

[Zn(C7H4BrO2)2(C10H14N2O)2(H2O)2] M = 857.89 Triclinic, a = 7.3761 (14) Å b = 8.677 (2) Å c = 16.072 (3) Å α = 84.32 (2)° β = 78.917 (17)° γ = 67.029 (18)° V = 929.1 (4) Å3 Z = 1 Mo Kα radiation μ = 2.87 mm−1 T = 294 (2) K 0.40 × 0.25 × 0.15 mm

Data collection

Enraf–Nonius TurboCAD-4 diffractometer Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.467, T max = 0.650 4005 measured reflections 3746 independent reflections 2570 reflections with I > 2σ(I) R int = 0.057 3 standard reflections frequency: 120 min intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.058 wR(F 2) = 0.177 S = 1.06 3746 reflections 242 parameters 16 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.87 e Å−3 Δρmin = −0.71 e Å−3 Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶). Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808027074/ci2660sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808027074/ci2660Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Zn(C7H4BrO2)2(C10H14N2O)2(H2O)2]Z = 1
Mr = 857.89F000 = 436
Triclinic, P1Dx = 1.533 Mg m−3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 7.3761 (14) ÅCell parameters from 25 reflections
b = 8.677 (2) Åθ = 5.5–13.7º
c = 16.072 (3) ŵ = 2.87 mm−1
α = 84.32 (2)ºT = 294 (2) K
β = 78.917 (17)ºBlock, colourless
γ = 67.029 (18)º0.40 × 0.25 × 0.15 mm
V = 929.1 (4) Å3
Enraf–Nonius TurboCAD-4 diffractometerRint = 0.057
Radiation source: fine-focus sealed tubeθmax = 26.3º
Monochromator: graphiteθmin = 2.6º
T = 294(2) Kh = −8→9
non–profiled ω scansk = 0→10
Absorption correction: ψ scan(North et al., 1968)l = −19→20
Tmin = 0.467, Tmax = 0.6503 standard reflections
4005 measured reflections every 120 min
3746 independent reflections intensity decay: 1%
2570 reflections with I > 2σ(I)
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.058H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.177  w = 1/[σ2(Fo2) + (0.1119P)2] where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
3746 reflectionsΔρmax = 0.87 e Å−3
242 parametersΔρmin = −0.71 e Å−3
16 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
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.
xyzUiso*/UeqOcc. (<1)
Br11.23888 (10)0.16715 (11)0.03176 (4)0.0880 (3)
Zn10.50000.00000.50000.0356 (2)
O10.6060 (4)0.1244 (4)0.39536 (19)0.0414 (7)
O20.4176 (5)0.1310 (4)0.3013 (2)0.0524 (8)
O3−0.3317 (5)0.3246 (4)0.6209 (2)0.0541 (9)
O40.2761 (5)−0.0147 (4)0.4372 (2)0.0461 (8)
H410.305 (9)0.035 (5)0.3919 (18)0.08 (2)*
H420.302 (7)−0.114 (2)0.425 (3)0.044 (13)*
N10.2774 (5)0.2327 (4)0.5504 (2)0.0364 (8)
N2−0.3276 (7)0.4115 (6)0.7461 (3)0.0619 (12)
C10.5726 (6)0.1316 (5)0.3210 (3)0.0392 (10)
C20.7355 (6)0.1412 (5)0.2502 (3)0.0373 (9)
C30.9095 (7)0.1478 (6)0.2676 (3)0.0420 (10)
H30.92590.14550.32370.050*
C41.0587 (7)0.1578 (6)0.2035 (3)0.0483 (11)
H41.17390.16400.21570.058*
C51.0324 (7)0.1583 (6)0.1206 (3)0.0503 (12)
C60.8638 (8)0.1483 (7)0.1016 (3)0.0536 (12)
H60.84930.14780.04540.064*
C70.7161 (7)0.1390 (6)0.1666 (3)0.0446 (11)
H70.60200.13130.15400.054*
C80.3051 (6)0.3789 (5)0.5402 (3)0.0416 (10)
H80.42480.38040.50930.050*
C90.1628 (7)0.5253 (6)0.5737 (3)0.0465 (11)
H90.18700.62370.56590.056*
C10−0.0151 (7)0.5256 (6)0.6188 (3)0.0451 (11)
H10−0.11270.62400.64190.054*
C11−0.0477 (6)0.3765 (5)0.6296 (3)0.0376 (9)
C120.1022 (6)0.2355 (5)0.5923 (3)0.0371 (9)
H120.07900.13690.59670.045*
C13−0.2459 (7)0.3684 (6)0.6665 (3)0.0441 (11)
C14−0.2330 (11)0.4635 (9)0.8056 (4)0.0805 (18)
H14A−0.10400.46070.77610.097*0.65 (3)
H14B−0.31460.57880.82020.097*0.65 (3)
H14C−0.32910.54300.84560.097*0.35 (3)
H14D−0.13870.50900.77550.097*0.35 (3)
C15−0.203 (3)0.365 (3)0.8832 (11)0.109 (6)0.65 (3)
H15A−0.14070.40920.91670.164*0.65 (3)
H15B−0.11970.25110.87010.164*0.65 (3)
H15C−0.33020.37040.91450.164*0.65 (3)
C15A−0.128 (4)0.301 (2)0.837 (3)0.099 (10)0.35 (3)
H15D−0.04730.30790.87550.148*0.35 (3)
H15E−0.04320.23270.79010.148*0.35 (3)
H15F−0.22080.25340.86520.148*0.35 (3)
C16−0.5345 (9)0.4168 (8)0.7762 (5)0.0759 (18)
H16A−0.59680.48890.82460.091*
H16B−0.61380.46240.73150.091*
C17−0.5281 (12)0.2459 (9)0.8008 (5)0.103 (3)
H17A−0.45430.20290.84670.154*
H17B−0.46410.17430.75320.154*
H17C−0.66170.24980.81840.154*
U11U22U33U12U13U23
Br10.0663 (5)0.1420 (7)0.0592 (4)−0.0549 (5)0.0153 (3)−0.0050 (4)
Zn10.0288 (4)0.0375 (4)0.0394 (4)−0.0128 (3)0.0004 (3)−0.0065 (3)
O10.0395 (17)0.0430 (17)0.0413 (18)−0.0169 (14)−0.0014 (13)−0.0052 (13)
O20.0335 (17)0.070 (2)0.055 (2)−0.0237 (16)−0.0073 (14)0.0055 (17)
O30.0423 (19)0.068 (2)0.062 (2)−0.0294 (17)−0.0069 (16)−0.0144 (17)
O40.0414 (18)0.048 (2)0.055 (2)−0.0232 (16)−0.0061 (15)−0.0058 (16)
N10.0312 (18)0.0340 (19)0.042 (2)−0.0118 (15)−0.0010 (14)−0.0038 (15)
N20.050 (3)0.082 (3)0.059 (3)−0.036 (2)0.008 (2)−0.016 (2)
C10.036 (2)0.030 (2)0.048 (3)−0.0112 (18)−0.0031 (19)−0.0024 (18)
C20.038 (2)0.033 (2)0.041 (2)−0.0152 (18)−0.0018 (18)−0.0043 (17)
C30.040 (2)0.047 (3)0.041 (2)−0.018 (2)−0.0066 (19)−0.0036 (19)
C40.039 (3)0.058 (3)0.051 (3)−0.024 (2)−0.003 (2)−0.001 (2)
C50.041 (3)0.057 (3)0.049 (3)−0.020 (2)0.005 (2)−0.005 (2)
C60.049 (3)0.073 (3)0.038 (3)−0.022 (3)−0.004 (2)−0.002 (2)
C70.037 (2)0.056 (3)0.043 (3)−0.020 (2)−0.0056 (19)−0.003 (2)
C80.033 (2)0.047 (3)0.048 (3)−0.020 (2)−0.0011 (19)−0.005 (2)
C90.047 (3)0.036 (2)0.058 (3)−0.018 (2)−0.004 (2)−0.008 (2)
C100.036 (2)0.038 (2)0.057 (3)−0.0086 (19)−0.004 (2)−0.014 (2)
C110.031 (2)0.041 (2)0.040 (2)−0.0115 (17)−0.0050 (17)−0.0080 (18)
C120.030 (2)0.038 (2)0.045 (2)−0.0152 (18)−0.0011 (17)−0.0041 (18)
C130.036 (2)0.043 (2)0.052 (3)−0.014 (2)−0.002 (2)−0.009 (2)
C140.080 (5)0.080 (4)0.075 (4)−0.028 (4)−0.003 (3)−0.006 (3)
C150.118 (9)0.139 (10)0.077 (8)−0.048 (7)−0.038 (7)0.006 (7)
C15A0.092 (12)0.089 (12)0.118 (14)−0.038 (9)−0.009 (9)−0.013 (8)
C160.059 (4)0.067 (4)0.094 (5)−0.025 (3)0.015 (3)−0.020 (3)
C170.116 (6)0.079 (5)0.102 (6)−0.047 (5)0.025 (5)0.001 (4)
Br1—C51.897 (5)C8—C91.372 (6)
Zn1—O1i2.097 (3)C8—H80.93
Zn1—O12.097 (3)C9—C101.371 (6)
Zn1—O4i2.143 (3)C9—H90.93
Zn1—O42.143 (3)C10—C111.394 (6)
Zn1—N1i2.157 (3)C10—H100.93
Zn1—N12.157 (3)C11—C121.383 (6)
O1—C11.257 (5)C11—C131.493 (6)
O2—C11.246 (5)C12—H120.93
O3—C131.226 (6)C14—C15A1.409 (16)
O4—H410.84 (4)C14—C151.441 (12)
O4—H420.84 (3)C14—H14A0.97
N1—C121.330 (5)C14—H14B0.97
N1—C81.352 (5)C14—H14C0.96
N2—C131.328 (6)C14—H14D0.96
N2—C141.481 (8)C15—H15A0.96
N2—C161.494 (7)C15—H15B0.96
C1—C21.510 (6)C15—H15C0.96
C2—C71.381 (6)C15A—H15D0.96
C2—C31.389 (6)C15A—H15E0.96
C3—C41.379 (6)C15A—H15F0.96
C3—H30.93C16—C171.481 (9)
C4—C51.382 (7)C16—H16A0.97
C4—H40.93C16—H16B0.97
C5—C61.373 (7)C17—H17A0.96
C6—C71.378 (6)C17—H17B0.96
C6—H60.93C17—H17C0.96
C7—H70.93
O1i—Zn1—O1180C9—C10—C11119.1 (4)
O1i—Zn1—O4i92.17 (12)C9—C10—H10120.4
O1—Zn1—O4i87.83 (12)C11—C10—H10120.4
O1i—Zn1—O487.83 (12)C12—C11—C10117.5 (4)
O1—Zn1—O492.17 (12)C12—C11—C13118.7 (4)
O4i—Zn1—O4180C10—C11—C13123.1 (4)
O1i—Zn1—N1i91.76 (12)N1—C12—C11123.9 (4)
O1—Zn1—N1i88.24 (12)N1—C12—H12118.0
O4i—Zn1—N1i86.71 (13)C11—C12—H12118.0
O4—Zn1—N1i93.29 (13)O3—C13—N2121.3 (4)
O1i—Zn1—N188.24 (12)O3—C13—C11118.3 (4)
O1—Zn1—N191.76 (12)N2—C13—C11120.3 (4)
O4i—Zn1—N193.29 (13)C15A—C14—N296.5 (14)
O4—Zn1—N186.71 (13)C15—C14—N2116.4 (8)
N1i—Zn1—N1180C15—C14—H14A108.2
C1—O1—Zn1126.3 (3)N2—C14—H14A108.2
Zn1—O4—H4196 (4)C15—C14—H14B108.2
Zn1—O4—H42111 (3)N2—C14—H14B108.2
H41—O4—H42107 (2)H14A—C14—H14B107.3
C12—N1—C8117.5 (3)C15A—C14—H14C117.8
C12—N1—Zn1119.3 (3)N2—C14—H14C112.5
C8—N1—Zn1123.1 (3)C15A—C14—H14D108.9
C13—N2—C14124.7 (5)N2—C14—H14D111.0
C13—N2—C16117.5 (5)H14C—C14—H14D109.6
C14—N2—C16117.7 (5)C14—C15—H15A109.5
O2—C1—O1125.5 (4)H14C—C15—H15A94.4
O2—C1—C2117.9 (4)C14—C15—H15B109.5
O1—C1—C2116.7 (4)H14C—C15—H15B145.2
C7—C2—C3118.7 (4)H15A—C15—H15B109.5
C7—C2—C1120.3 (4)C14—C15—H15C109.5
C3—C2—C1120.9 (4)H14C—C15—H15C84.6
C4—C3—C2121.4 (5)H15A—C15—H15C109.5
C4—C3—H3119.3H15B—C15—H15C109.5
C2—C3—H3119.3C14—C15A—H15D109.5
C3—C4—C5118.2 (5)C14—C15A—H15E109.5
C3—C4—H4120.9H15D—C15A—H15E109.5
C5—C4—H4120.9C14—C15A—H15F109.5
C6—C5—C4121.6 (4)H15D—C15A—H15F109.5
C6—C5—Br1119.7 (4)H15E—C15A—H15F109.5
C4—C5—Br1118.6 (4)C17—C16—N2110.0 (6)
C5—C6—C7119.3 (5)C17—C16—H16A109.7
C5—C6—H6120.3N2—C16—H16A109.7
C7—C6—H6120.3C17—C16—H16B109.7
C6—C7—C2120.7 (4)N2—C16—H16B109.7
C6—C7—H7119.6H16A—C16—H16B108.2
C2—C7—H7119.6C16—C17—H17A109.5
N1—C8—C9122.3 (4)C16—C17—H17B109.5
N1—C8—H8118.8H17A—C17—H17B109.5
C9—C8—H8118.8C16—C17—H17C109.5
C8—C9—C10119.6 (4)H17A—C17—H17C109.5
C8—C9—H9120.2H17B—C17—H17C109.5
C10—C9—H9120.2
O4i—Zn1—O1—C1163.0 (3)C3—C2—C7—C6−1.9 (7)
O4—Zn1—O1—C1−17.0 (3)C1—C2—C7—C6179.8 (4)
N1i—Zn1—O1—C176.3 (3)C12—N1—C8—C92.3 (7)
N1—Zn1—O1—C1−103.7 (3)Zn1—N1—C8—C9−179.1 (3)
O1i—Zn1—N1—C12−33.6 (3)N1—C8—C9—C10−0.5 (7)
O1—Zn1—N1—C12146.4 (3)C8—C9—C10—C110.0 (7)
O4i—Zn1—N1—C12−125.7 (3)C9—C10—C11—C12−1.2 (7)
O4—Zn1—N1—C1254.3 (3)C9—C10—C11—C13−170.8 (5)
O1i—Zn1—N1—C8147.8 (3)C8—N1—C12—C11−3.7 (6)
O1—Zn1—N1—C8−32.2 (3)Zn1—N1—C12—C11177.6 (3)
O4i—Zn1—N1—C855.7 (4)C10—C11—C12—N13.2 (7)
O4—Zn1—N1—C8−124.3 (4)C13—C11—C12—N1173.3 (4)
Zn1—O1—C1—O231.6 (6)C14—N2—C13—O3179.1 (5)
Zn1—O1—C1—C2−148.2 (3)C16—N2—C13—O3−4.4 (7)
O2—C1—C2—C7−3.8 (6)C14—N2—C13—C11−2.4 (8)
O1—C1—C2—C7176.0 (4)C16—N2—C13—C11174.1 (5)
O2—C1—C2—C3177.9 (4)C12—C11—C13—O3−54.7 (6)
O1—C1—C2—C3−2.3 (6)C10—C11—C13—O3114.9 (5)
C7—C2—C3—C42.2 (6)C12—C11—C13—N2126.8 (5)
C1—C2—C3—C4−179.5 (4)C10—C11—C13—N2−63.7 (7)
C2—C3—C4—C5−1.0 (7)C13—N2—C14—C15A−87.7 (16)
C3—C4—C5—C6−0.4 (8)C16—N2—C14—C15A95.7 (16)
C3—C4—C5—Br1−178.7 (4)C13—N2—C14—C15−121.7 (12)
C4—C5—C6—C70.6 (8)C16—N2—C14—C1561.7 (13)
Br1—C5—C6—C7178.9 (4)C13—N2—C16—C1781.6 (7)
C5—C6—C7—C20.6 (8)C14—N2—C16—C17−101.6 (7)
D—H···AD—HH···AD···AD—H···A
O4—H41···O20.84 (4)1.83 (5)2.658 (5)168 (3)
O4—H42···O3ii0.84 (3)1.95 (3)2.786 (6)169 (2)
Zn1—O12.097 (3)
Zn1—O42.143 (3)
Zn1—N12.157 (3)
O1—Zn1—O4i87.83 (12)
O1—Zn1—O492.17 (12)
O1—Zn1—N1i88.24 (12)
O4—Zn1—N1i93.29 (13)
O1—Zn1—N191.76 (12)
O4—Zn1—N186.71 (13)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
O4—H41⋯O20.84 (4)1.83 (5)2.658 (5)168 (3)
O4—H42⋯O3ii0.84 (3)1.95 (3)2.786 (6)169 (2)

Symmetry code: (ii) .

  1 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290
  1 in total
  1 in total

1.  Diaqua-bis(5-bromo-2-hydroxy-benzoato)bis-(N-methyl-nicotinamide)zinc(II).

Authors:  Zuzana Bujdošová; Juraj Kuchár; Katarína Györyová
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-03-13
  1 in total

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