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The title compound, [Zn(C7H4BrO2)2], is a square planar zinc(II)–phenolate complex. The ZnII atom lies on an inversion center and is coordinated by four O atoms from two deprotonated 5-bromo-2-hydroxy­benzaldehyde mol­ecules acting as bidentate chelate ligands.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805040432/sj6179sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805040432/sj6179Isup2.hkl
Contains datablock I

CCDC reference: 1255823

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.010 Å
  • R factor = 0.058
  • wR factor = 0.143
  • Data-to-parameter ratio = 15.9

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for O2 - C7 .. 7.01 su
Alert level C PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O2 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 10
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

Zinc(II) compounds are very important in biological chemistry (Casella & Gullotti, 1981). As part of our work aimed at understanding the structures of zinc(II) compounds, we report here a new mononuclear zinc(II) compound, (I), Fig. 1. Compound (I) is isostructural with the copper(II) compound reported recently (Sun & Gao, 2005), and structurally similar to the related bis(salicylaldehydo)zinc(II) complex (Xiong & Liu, 2005). In (I), the Zn(II) ion lies on an inversion center and binds to the O atoms of two bidentate chelate 5-bromo-2–2-formylphenolate ligands. The overall coordination geometry is square planar. The bond lengths (Table 1) around the metal center are comparable to the values observed in the compounds cited above.

Experimental top

Crystals were formed by the slow evaporation of the solvent from a mixture of 5-bromo-2-hydroxyaldehyde (0.2 mmol, 40.3 mg) and zinc acetate tetrahydrate (0.1 mmol, 25.6 mg) in ethanol (15 ml).

Refinement top

H atoms attached to C atoms were included in the refinement in calculated positions in the riding-model approximation [C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C)].

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. Structure of (I). Displacement ellipsoids are drawn at the 30% probability level. Atoms labelled with the suffix A are at the symmetry position (−x, 1 − y, 1 − z).
Bis(4-bromo-2-formylphenolato-κ2O,O')zinc(II) top
Crystal data top
[Zn(C7H4BrO2)2]F(000) = 448
Mr = 465.39Dx = 2.096 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 709 reflections
a = 16.265 (4) Åθ = 2.1–24.3°
b = 5.6182 (14) ŵ = 7.09 mm1
c = 8.109 (2) ÅT = 298 K
β = 95.543 (4)°Needle, yellow
V = 737.5 (3) Å30.13 × 0.11 × 0.09 mm
Z = 2
Data collection top
Bruker APEX area-detector
diffractometer
1603 independent reflections
Radiation source: fine-focus sealed tube988 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.067
ω scansθmax = 27.0°, θmin = 1.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 2020
Tmin = 0.427, Tmax = 0.528k = 67
5858 measured reflectionsl = 1010
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0549P)2 + 1.3455P]
where P = (Fo2 + 2Fc2)/3
1603 reflections(Δ/σ)max = 0.001
101 parametersΔρmax = 0.49 e Å3
0 restraintsΔρmin = 0.53 e Å3
Crystal data top
[Zn(C7H4BrO2)2]V = 737.5 (3) Å3
Mr = 465.39Z = 2
Monoclinic, P21/cMo Kα radiation
a = 16.265 (4) ŵ = 7.09 mm1
b = 5.6182 (14) ÅT = 298 K
c = 8.109 (2) Å0.13 × 0.11 × 0.09 mm
β = 95.543 (4)°
Data collection top
Bruker APEX area-detector
diffractometer
1603 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
988 reflections with I > 2σ(I)
Tmin = 0.427, Tmax = 0.528Rint = 0.067
5858 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0580 restraints
wR(F2) = 0.143H-atom parameters constrained
S = 1.02Δρmax = 0.49 e Å3
1603 reflectionsΔρmin = 0.53 e Å3
101 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
xyzUiso*/Ueq
Zn10.00000.50000.50000.0453 (4)
Br10.42856 (5)0.33819 (19)0.30459 (12)0.0746 (4)
O10.1005 (3)0.6522 (7)0.5198 (6)0.0410 (11)
O20.0384 (4)0.2374 (9)0.3882 (7)0.0652 (15)
C10.1711 (4)0.5764 (12)0.4724 (8)0.0378 (16)
C20.2433 (5)0.7122 (12)0.5102 (9)0.0462 (18)
H20.24020.85370.56890.035 (17)*
C30.3184 (4)0.6416 (14)0.4622 (9)0.0504 (19)
H30.36500.73510.48850.06 (2)*
C40.3251 (4)0.4316 (13)0.3762 (9)0.0451 (18)
C50.2581 (4)0.2907 (13)0.3400 (9)0.0442 (17)
H50.26390.14890.28300.07 (3)*
C60.1800 (4)0.3563 (11)0.3867 (8)0.0359 (15)
C70.1119 (4)0.1953 (12)0.3515 (8)0.0416 (17)
H70.12140.05180.29940.042 (19)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0514 (8)0.0385 (7)0.0458 (7)0.0011 (6)0.0031 (6)0.0034 (6)
Br10.0481 (5)0.0931 (8)0.0850 (7)0.0007 (5)0.0184 (5)0.0148 (6)
O10.038 (3)0.033 (3)0.053 (3)0.000 (2)0.005 (2)0.005 (2)
O20.077 (4)0.054 (3)0.064 (4)0.001 (3)0.006 (3)0.006 (3)
C10.046 (4)0.032 (3)0.035 (4)0.000 (3)0.002 (3)0.000 (3)
C20.061 (5)0.028 (4)0.048 (4)0.002 (3)0.001 (4)0.008 (3)
C30.039 (4)0.058 (5)0.053 (5)0.007 (4)0.004 (3)0.008 (4)
C40.042 (4)0.046 (4)0.047 (4)0.007 (3)0.006 (3)0.000 (4)
C50.055 (5)0.034 (4)0.044 (4)0.002 (3)0.006 (3)0.003 (3)
C60.037 (4)0.028 (4)0.042 (4)0.004 (3)0.000 (3)0.001 (3)
C70.047 (4)0.037 (4)0.043 (4)0.014 (3)0.010 (3)0.009 (3)
Geometric parameters (Å, º) top
Zn1—O1i1.838 (4)C2—C31.375 (10)
Zn1—O11.838 (4)C2—H20.9300
Zn1—O2i1.870 (5)C3—C41.380 (10)
Zn1—O21.870 (5)C3—H30.9301
Br1—C41.905 (7)C4—C51.356 (10)
O1—C11.317 (8)C5—C61.409 (9)
O2—C71.283 (8)C5—H50.9300
C1—C21.409 (9)C6—C71.437 (9)
C1—C61.432 (9)C7—H70.9300
O1i—Zn1—O1180.0C2—C3—H3119.8
O1i—Zn1—O2i94.2 (2)C4—C3—H3119.7
O1—Zn1—O2i85.8 (2)C5—C4—C3120.4 (7)
O1i—Zn1—O285.8 (2)C5—C4—Br1119.2 (6)
O1—Zn1—O294.2 (2)C3—C4—Br1120.4 (6)
O2i—Zn1—O2180.0C4—C5—C6121.0 (7)
C1—O1—Zn1128.1 (4)C4—C5—H5119.4
C7—O2—Zn1128.3 (5)C6—C5—H5119.6
O1—C1—C2119.6 (6)C5—C6—C1119.5 (6)
O1—C1—C6123.6 (6)C5—C6—C7118.7 (6)
C2—C1—C6116.9 (6)C1—C6—C7121.8 (6)
C3—C2—C1121.7 (7)O2—C7—C6123.8 (6)
C3—C2—H2119.0O2—C7—H7117.7
C1—C2—H2119.3C6—C7—H7118.5
C2—C3—C4120.4 (7)
Symmetry code: (i) x, y+1, z+1.

Experimental details

Crystal data
Chemical formula[Zn(C7H4BrO2)2]
Mr465.39
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)16.265 (4), 5.6182 (14), 8.109 (2)
β (°) 95.543 (4)
V3)737.5 (3)
Z2
Radiation typeMo Kα
µ (mm1)7.09
Crystal size (mm)0.13 × 0.11 × 0.09
Data collection
DiffractometerBruker APEX area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.427, 0.528
No. of measured, independent and
observed [I > 2σ(I)] reflections
5858, 1603, 988
Rint0.067
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.058, 0.143, 1.02
No. of reflections1603
No. of parameters101
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.49, 0.53

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SAINT, SHELXTL (Bruker, 2000), SHELXTL.

Selected geometric parameters (Å, º) top
Zn1—O1i1.838 (4)Zn1—O2i1.870 (5)
Zn1—O11.838 (4)Zn1—O21.870 (5)
O1i—Zn1—O1180.0O1i—Zn1—O285.8 (2)
O1i—Zn1—O2i94.2 (2)O1—Zn1—O294.2 (2)
O1—Zn1—O2i85.8 (2)O2i—Zn1—O2180.0
Symmetry code: (i) x, y+1, z+1.
 

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