supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportcited insimilar papers buy article online

Acta Cryst. (2007). E63, m1702    [ doi:10.1107/S1600536807023136 ]

Bis[2,4-dibromo-6-(cyclopropyliminomethyl)phenolato]zinc(II)

W.-B. Yuan, H.-W. Xu, J.-X. Li, M. Liu and Q. Zhang

Abstract top

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.

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.

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 m−3
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 mm−1
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)
graphiteRint = 0.031
ω scansθmax = 27.5°, θmin = 1.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −9→9
Tmin = 0.182, Tmax = 0.187k = −12→12
12652 measured reflectionsl = −20→20
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 Å−3
0 restraintsΔρmin = −0.73 e Å−3
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 mm−1
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 reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.037H-atom parameters constrained
wR(F2) = 0.086Δρmax = 0.65 e Å−3
S = 1.04Δρmin = −0.73 e Å−3
4962 reflectionsAbsolute structure: ?
262 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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, °) 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
Acknowledgements top

The authors thank the National Natural Science Foundation of Hainan Province (No. 20602) and the Open Fund (No. hnfc2006005) of Hainan Provincial Key Laboratory of Fine Chemicals for financial support.

references
References top

Bruker (1997). SHELXTL (Version 5.1). Bruker AXS Inc., Madison, Wisconsin, USA.

Bruker (1998). SMART (Version 5.628) and SAINT (Version 6.02). Bruker AXS Inc., Madison, Wisconsin, USA.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (1997). SHELXTL97, SHELXS97 and SHELXL97. University of Göttingen, Germany.

You, Z.-L. (2005a). Acta Cryst. E61, m2499–m2500.

You, Z.-L. (2005b). Acta Cryst. E61, m2501–m2502.

Yuan, W.-B. & Zhang, Q. (2005). Acta Cryst. E61, m1883–m1884.