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The title complex, [Zn(C10H8Br2NO)2], is a mononuclear zinc(II) compound. The ZnII ion is four-coordinated by two N and two O atoms from two Schiff base ligands, forming a tetra­hedral coordination.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807023136/fj2029sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807023136/fj2029Isup2.hkl
Contains datablock I

CCDC reference: 650696

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.037
  • wR factor = 0.086
  • Data-to-parameter ratio = 18.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT431_ALERT_2_C Short Inter HL..A Contact Br2 .. O2 .. 3.32 Ang. PLAT431_ALERT_2_C Short Inter HL..A Contact Br4 .. O1 .. 3.24 Ang.
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Zn1 (2) 2.04
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Comment top

Recently, we have reported the structure of a Schiff base copper(II) complex (Yuan & Zhang, 2005). As an extension of our investigations in this area, we report here the title compound, a new mononuclear Schiff base zinc(II) complex, (I).

In (I), the Zn atom is four-coordinated by two N and two O atoms from two Schiff base ligands, forming a tetrahedral coordination (Fig. 1). The bond lengths and angles are comparable to the values observed in the similar Schiff base zinc(II) complexes (You, 2005a,b).

Related literature top

For related literature, see: You (2005a, 2005b); Yuan & Zhang (2005).

Experimental top

3,5-Dibromo-2-hydroxybenzaldehyde (1.0 mmol, 280.0 mg), cyclopropylamine (1.0 mmol, 57.0 mg) and zinc dichloride (0.5 mmol, 68.1 mg) were dissolved in a methanol solution (50 ml). The mixture was stirred at room temperature for 30 min and filtered. After keeping the filtrate in air for 8 days, colorless block-shaped crystals were formed.

Refinement top

H atoms were placed in idealized positions and constrained to ride on their parent atoms, with C—H = 0.93–0.97 Å and Uiso(H) = 1.2 times Ueq(C). The maximum residual electron density peak is observed 1.91 Å from Br3. The minimum residual electron density peak is observed 0.86 Å from Br1.

Structure description top

Recently, we have reported the structure of a Schiff base copper(II) complex (Yuan & Zhang, 2005). As an extension of our investigations in this area, we report here the title compound, a new mononuclear Schiff base zinc(II) complex, (I).

In (I), the Zn atom is four-coordinated by two N and two O atoms from two Schiff base ligands, forming a tetrahedral coordination (Fig. 1). The bond lengths and angles are comparable to the values observed in the similar Schiff base zinc(II) complexes (You, 2005a,b).

For related literature, see: You (2005a, 2005b); Yuan & Zhang (2005).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The structure of (I). Displacement ellipsoids are drawn at the 30% probability level.
Bis[2,4-dibromo-6-(cyclopropyliminomethyl)phenolato]zinc(II) top
Crystal data top
[Zn(C10H8Br2NO)2]Z = 2
Mr = 701.36F(000) = 672
Triclinic, P1Dx = 2.122 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.5490 (15) ÅCell parameters from 3389 reflections
b = 9.883 (2) Åθ = 2.2–26.0°
c = 15.814 (3) ŵ = 8.42 mm1
α = 78.34 (3)°T = 298 K
β = 82.49 (2)°Block, colorless
γ = 72.24 (3)°0.21 × 0.20 × 0.20 mm
V = 1097.4 (4) Å3
Data collection top
Bruker SMART 1000 CCD area detector
diffractometer
4962 independent reflections
Radiation source: fine-focus sealed tube3772 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
ω scansθmax = 27.5°, θmin = 1.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 99
Tmin = 0.182, Tmax = 0.187k = 1212
12652 measured reflectionsl = 2020
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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0384P)2 + 0.0662P]
where P = (Fo2 + 2Fc2)/3
4962 reflections(Δ/σ)max < 0.001
262 parametersΔρmax = 0.65 e Å3
0 restraintsΔρmin = 0.73 e Å3
Crystal data top
[Zn(C10H8Br2NO)2]γ = 72.24 (3)°
Mr = 701.36V = 1097.4 (4) Å3
Triclinic, P1Z = 2
a = 7.5490 (15) ÅMo Kα radiation
b = 9.883 (2) ŵ = 8.42 mm1
c = 15.814 (3) ÅT = 298 K
α = 78.34 (3)°0.21 × 0.20 × 0.20 mm
β = 82.49 (2)°
Data collection top
Bruker SMART 1000 CCD area detector
diffractometer
4962 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3772 reflections with I > 2σ(I)
Tmin = 0.182, Tmax = 0.187Rint = 0.031
12652 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.086H-atom parameters constrained
S = 1.04Δρmax = 0.65 e Å3
4962 reflectionsΔρmin = 0.73 e Å3
262 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
Zn10.63891 (6)0.71541 (4)0.74530 (2)0.03400 (12)
Br10.26207 (8)0.94742 (6)0.97427 (3)0.07098 (18)
Br20.68209 (6)0.50762 (5)1.21708 (2)0.05179 (13)
Br30.27136 (7)0.65425 (6)0.53715 (3)0.05651 (14)
Br40.68691 (6)0.92573 (4)0.27077 (2)0.04488 (12)
O10.5050 (4)0.7705 (3)0.84927 (15)0.0408 (6)
O20.5105 (3)0.7210 (3)0.64830 (14)0.0390 (6)
N10.7902 (4)0.5186 (3)0.80191 (18)0.0315 (7)
N20.7973 (4)0.8430 (3)0.68016 (18)0.0346 (7)
C10.6930 (5)0.5771 (4)0.9477 (2)0.0305 (8)
C20.5521 (5)0.7084 (4)0.9267 (2)0.0313 (8)
C30.4576 (5)0.7739 (4)0.9983 (2)0.0383 (9)
C40.4982 (5)0.7182 (4)1.0822 (2)0.0395 (9)
H40.43300.76601.12680.047*
C50.6371 (5)0.5904 (4)1.1000 (2)0.0367 (9)
C60.7302 (5)0.5184 (4)1.0352 (2)0.0366 (9)
H60.81910.42981.04850.044*
C70.7958 (5)0.4884 (4)0.8844 (2)0.0354 (8)
H70.87510.39920.90630.042*
C80.9041 (5)0.4100 (4)0.7528 (2)0.0381 (9)
H80.99310.32810.78530.046*
C90.9640 (6)0.4547 (4)0.6611 (2)0.0478 (11)
H9A0.92400.55660.63680.057*
H9B1.08710.40280.63930.057*
C100.8206 (6)0.3770 (5)0.6822 (3)0.0512 (11)
H10A0.85590.27760.67350.061*
H10B0.69280.43140.67090.061*
C110.6953 (5)0.8382 (4)0.5393 (2)0.0306 (8)
C120.5560 (5)0.7659 (4)0.5682 (2)0.0313 (8)
C130.4627 (5)0.7448 (4)0.5020 (2)0.0353 (8)
C140.5031 (5)0.7891 (4)0.4152 (2)0.0355 (8)
H140.43840.77280.37390.043*
C150.6398 (5)0.8575 (4)0.3902 (2)0.0344 (8)
C160.7330 (5)0.8838 (4)0.4509 (2)0.0344 (8)
H160.82260.93280.43320.041*
C170.7993 (5)0.8760 (4)0.5980 (2)0.0361 (8)
H170.87760.93160.57190.043*
C180.9148 (6)0.8962 (4)0.7221 (2)0.0419 (9)
H181.00790.93400.68370.050*
C190.9688 (7)0.8296 (5)0.8106 (3)0.0531 (11)
H19A0.92380.74850.83900.064*
H19B1.09260.82410.82420.064*
C200.8322 (7)0.9723 (5)0.7968 (3)0.0592 (12)
H20A0.87201.05470.80170.071*
H20B0.70310.97900.81650.071*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0398 (3)0.0374 (2)0.0239 (2)0.01177 (19)0.00172 (17)0.00263 (17)
Br10.0755 (4)0.0668 (3)0.0449 (3)0.0230 (3)0.0076 (2)0.0167 (2)
Br20.0531 (3)0.0735 (3)0.0269 (2)0.0183 (2)0.00901 (17)0.00014 (19)
Br30.0553 (3)0.0854 (4)0.0435 (2)0.0439 (3)0.0016 (2)0.0088 (2)
Br40.0519 (3)0.0523 (3)0.02541 (19)0.0129 (2)0.00125 (16)0.00065 (16)
O10.0453 (16)0.0445 (16)0.0227 (12)0.0010 (13)0.0005 (11)0.0030 (11)
O20.0416 (15)0.0552 (17)0.0236 (13)0.0246 (13)0.0013 (11)0.0014 (11)
N10.0328 (17)0.0344 (16)0.0269 (15)0.0097 (13)0.0008 (12)0.0064 (12)
N20.0398 (18)0.0368 (17)0.0291 (16)0.0136 (14)0.0036 (13)0.0052 (13)
C10.0296 (19)0.0345 (19)0.0263 (17)0.0088 (15)0.0002 (14)0.0045 (14)
C20.0309 (19)0.040 (2)0.0248 (17)0.0131 (16)0.0010 (14)0.0050 (15)
C30.035 (2)0.040 (2)0.035 (2)0.0048 (17)0.0021 (16)0.0050 (16)
C40.045 (2)0.053 (2)0.0255 (18)0.019 (2)0.0018 (16)0.0116 (17)
C50.040 (2)0.050 (2)0.0258 (18)0.0207 (19)0.0097 (16)0.0008 (16)
C60.038 (2)0.039 (2)0.033 (2)0.0118 (17)0.0072 (16)0.0022 (16)
C70.035 (2)0.032 (2)0.037 (2)0.0090 (16)0.0040 (16)0.0038 (16)
C80.038 (2)0.038 (2)0.037 (2)0.0055 (17)0.0017 (16)0.0115 (16)
C90.054 (3)0.045 (2)0.041 (2)0.009 (2)0.0113 (19)0.0154 (18)
C100.052 (3)0.056 (3)0.054 (3)0.015 (2)0.005 (2)0.027 (2)
C110.031 (2)0.0312 (19)0.0289 (18)0.0081 (15)0.0053 (15)0.0036 (14)
C120.032 (2)0.033 (2)0.0257 (17)0.0060 (16)0.0009 (14)0.0047 (15)
C130.034 (2)0.037 (2)0.036 (2)0.0121 (17)0.0001 (16)0.0066 (16)
C140.039 (2)0.039 (2)0.0295 (19)0.0097 (17)0.0057 (16)0.0087 (16)
C150.035 (2)0.036 (2)0.0261 (18)0.0037 (16)0.0023 (15)0.0046 (15)
C160.037 (2)0.034 (2)0.034 (2)0.0146 (17)0.0007 (16)0.0047 (16)
C170.037 (2)0.040 (2)0.035 (2)0.0172 (17)0.0014 (16)0.0058 (16)
C180.047 (2)0.051 (2)0.035 (2)0.024 (2)0.0004 (17)0.0103 (17)
C190.064 (3)0.058 (3)0.047 (2)0.030 (2)0.021 (2)0.001 (2)
C200.062 (3)0.065 (3)0.059 (3)0.018 (3)0.011 (2)0.028 (2)
Geometric parameters (Å, º) top
Zn1—O11.901 (2)C8—C101.486 (5)
Zn1—O21.902 (2)C8—H80.9800
Zn1—N12.024 (3)C9—C101.477 (6)
Zn1—N22.038 (3)C9—H9A0.9700
Br1—C31.898 (4)C9—H9B0.9700
Br2—C51.897 (3)C10—H10A0.9700
Br3—C131.890 (4)C10—H10B0.9700
Br4—C151.898 (3)C11—C161.399 (5)
O1—C21.296 (4)C11—C121.423 (5)
O2—C121.293 (4)C11—C171.459 (5)
N1—C71.281 (4)C12—C131.416 (5)
N1—C81.447 (4)C13—C141.378 (5)
N2—C171.274 (4)C14—C151.375 (5)
N2—C181.443 (5)C14—H140.9300
C1—C21.415 (5)C15—C161.369 (5)
C1—C61.416 (5)C16—H160.9300
C1—C71.453 (5)C17—H170.9300
C2—C31.419 (5)C18—C191.473 (5)
C3—C41.366 (5)C18—C201.493 (5)
C4—C51.378 (5)C18—H180.9800
C4—H40.9300C19—C201.465 (6)
C5—C61.360 (5)C19—H19A0.9700
C6—H60.9300C19—H19B0.9700
C7—H70.9300C20—H20A0.9700
C8—C91.483 (5)C20—H20B0.9700
O1—Zn1—O2120.70 (11)H9A—C9—H9B114.9
O1—Zn1—N195.56 (11)C9—C10—C860.0 (3)
O2—Zn1—N1116.58 (12)C9—C10—H10A117.8
O1—Zn1—N2116.16 (12)C8—C10—H10A117.8
O2—Zn1—N295.52 (11)C9—C10—H10B117.8
N1—Zn1—N2113.73 (12)C8—C10—H10B117.8
C2—O1—Zn1125.0 (2)H10A—C10—H10B114.9
C12—O2—Zn1126.1 (2)C16—C11—C12120.7 (3)
C7—N1—C8117.0 (3)C16—C11—C17116.0 (3)
C7—N1—Zn1120.1 (2)C12—C11—C17123.3 (3)
C8—N1—Zn1122.8 (2)O2—C12—C13119.5 (3)
C17—N2—C18116.9 (3)O2—C12—C11125.0 (3)
C17—N2—Zn1119.8 (3)C13—C12—C11115.4 (3)
C18—N2—Zn1123.3 (2)C14—C13—C12123.2 (3)
C2—C1—C6120.4 (3)C14—C13—Br3119.7 (3)
C2—C1—C7123.5 (3)C12—C13—Br3117.1 (3)
C6—C1—C7115.8 (3)C15—C14—C13119.5 (3)
O1—C2—C1125.5 (3)C15—C14—H14120.3
O1—C2—C3119.2 (3)C13—C14—H14120.3
C1—C2—C3115.2 (3)C16—C15—C14120.4 (3)
C4—C3—C2123.8 (3)C16—C15—Br4120.3 (3)
C4—C3—Br1119.1 (3)C14—C15—Br4119.2 (3)
C2—C3—Br1117.1 (3)C15—C16—C11120.9 (3)
C3—C4—C5119.2 (3)C15—C16—H16119.5
C3—C4—H4120.4C11—C16—H16119.5
C5—C4—H4120.4N2—C17—C11128.7 (3)
C6—C5—C4120.7 (3)N2—C17—H17115.7
C6—C5—Br2120.2 (3)C11—C17—H17115.7
C4—C5—Br2118.9 (3)N2—C18—C19120.8 (3)
C5—C6—C1120.6 (3)N2—C18—C20118.8 (4)
C5—C6—H6119.7C19—C18—C2059.2 (3)
C1—C6—H6119.7N2—C18—H18115.5
N1—C7—C1127.7 (3)C19—C18—H18115.5
N1—C7—H7116.1C20—C18—H18115.5
C1—C7—H7116.1C20—C19—C1861.1 (3)
N1—C8—C9119.1 (3)C20—C19—H19A117.7
N1—C8—C10118.5 (3)C18—C19—H19A117.7
C9—C8—C1059.7 (3)C20—C19—H19B117.7
N1—C8—H8115.9C18—C19—H19B117.7
C9—C8—H8115.9H19A—C19—H19B114.8
C10—C8—H8115.9C19—C20—C1859.7 (3)
C10—C9—C860.2 (3)C19—C20—H20A117.8
C10—C9—H9A117.7C18—C20—H20A117.8
C8—C9—H9A117.7C19—C20—H20B117.8
C10—C9—H9B117.7C18—C20—H20B117.8
C8—C9—H9B117.7H20A—C20—H20B114.9

Experimental details

Crystal data
Chemical formula[Zn(C10H8Br2NO)2]
Mr701.36
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)7.5490 (15), 9.883 (2), 15.814 (3)
α, β, γ (°)78.34 (3), 82.49 (2), 72.24 (3)
V3)1097.4 (4)
Z2
Radiation typeMo Kα
µ (mm1)8.42
Crystal size (mm)0.21 × 0.20 × 0.20
Data collection
DiffractometerBruker SMART 1000 CCD area detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.182, 0.187
No. of measured, independent and
observed [I > 2σ(I)] reflections
12652, 4962, 3772
Rint0.031
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.086, 1.04
No. of reflections4962
No. of parameters262
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.65, 0.73

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.

 

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