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The title compound, [ZnBr2(C12H17ClN2O)], is a mononuclear Schiff base zinc(II) complex. The Zn atom in the compound is four-coordinated by one imine N and one phenolate O atom of the Schiff base ligand and by two terminal Br anions, forming a tetra­hedral geometry. In the crystal structure, mol­ecules are linked through inter­molecular N—H...O hydrogen bonds, forming chains running along the c axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807010379/hg2197sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807010379/hg2197Isup2.hkl
Contains datablock I

CCDC reference: 647228

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.011 Å
  • R factor = 0.060
  • wR factor = 0.179
  • Data-to-parameter ratio = 19.6

checkCIF/PLATON results

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Alert level B PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Br2 - Zn1 .. 18.78 su
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.92 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.88 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.55 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N2 PLAT245_ALERT_2_C U(iso) H2 Smaller than U(eq) N2 by ... 0.01 AngSq PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 11
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.919 Tmax scaled 0.499 Tmin scaled 0.349
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXTL.

Dibromido{4-chloro-2-[3-(dimethylamino)propyliminomethyl]phenolato}zinc(II) top
Crystal data top
[ZnBr2(C12H17ClN2O)]F(000) = 912
Mr = 465.92Dx = 1.828 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1555 reflections
a = 7.103 (1) Åθ = 2.5–24.9°
b = 14.851 (2) ŵ = 6.32 mm1
c = 16.058 (2) ÅT = 298 K
β = 91.886 (2)°Block, colourless
V = 1693.0 (4) Å30.19 × 0.11 × 0.11 mm
Z = 4
Data collection top
Bruker APEXII area-detector
diffractometer
3481 independent reflections
Radiation source: fine-focus sealed tube2178 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.065
ω scansθmax = 26.5°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 88
Tmin = 0.380, Tmax = 0.543k = 1818
12802 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)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.179H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0779P)2 + 5.4115P]
where P = (Fo2 + 2Fc2)/3
3481 reflections(Δ/σ)max < 0.001
178 parametersΔρmax = 0.66 e Å3
1 restraintΔρmin = 1.21 e Å3
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
Zn10.73282 (12)0.74314 (6)0.89473 (5)0.0419 (3)
Br10.89523 (14)0.60775 (7)0.91491 (6)0.0627 (3)
Br20.86093 (16)0.86927 (8)0.96877 (7)0.0754 (4)
Cl10.0431 (3)0.99137 (17)0.66569 (15)0.0652 (7)
O10.6791 (7)0.7639 (4)0.7763 (3)0.0488 (14)
N10.4592 (8)0.7318 (4)0.9220 (4)0.0368 (14)
N20.3792 (11)0.8561 (5)1.1716 (4)0.0510 (18)
C10.3667 (9)0.8206 (5)0.8017 (4)0.0331 (16)
C20.5303 (10)0.8131 (5)0.7535 (4)0.0379 (17)
C30.5270 (11)0.8577 (6)0.6772 (5)0.048 (2)
H30.62940.85090.64320.058*
C40.3808 (12)0.9111 (6)0.6499 (5)0.047 (2)
H40.38410.93950.59840.056*
C50.2291 (11)0.9220 (5)0.6996 (5)0.0400 (18)
C60.2183 (10)0.8745 (5)0.7728 (5)0.0417 (19)
H60.10990.87840.80360.050*
C70.3358 (11)0.7707 (6)0.8774 (5)0.0413 (18)
H70.21240.76710.89470.050*
C80.4021 (11)0.6822 (6)0.9963 (5)0.0439 (19)
H8A0.45750.62250.99600.053*
H8B0.26620.67540.99460.053*
C90.4632 (10)0.7303 (5)1.0761 (5)0.0409 (18)
H9A0.43770.69201.12340.049*
H9B0.59790.74101.07590.049*
C100.3622 (12)0.8188 (6)1.0855 (5)0.049 (2)
H10A0.41310.86211.04700.059*
H10B0.22990.81061.07050.059*
C110.2718 (18)0.9395 (8)1.1792 (7)0.094 (4)
H11A0.30740.98091.13660.142*
H11B0.29780.96571.23300.142*
H11C0.13970.92661.17300.142*
C120.5799 (16)0.8701 (8)1.2007 (6)0.081 (3)
H12A0.64400.90551.16030.121*
H12B0.64120.81281.20710.121*
H12C0.58290.90101.25320.121*
H20.308 (9)0.821 (4)1.203 (4)0.04 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0327 (5)0.0589 (6)0.0344 (5)0.0040 (4)0.0042 (4)0.0012 (4)
Br10.0628 (6)0.0655 (6)0.0594 (6)0.0162 (5)0.0044 (5)0.0043 (5)
Br20.0678 (7)0.0785 (8)0.0799 (8)0.0102 (5)0.0023 (6)0.0036 (6)
Cl10.0664 (15)0.0631 (15)0.0661 (15)0.0235 (12)0.0007 (12)0.0105 (12)
O10.039 (3)0.075 (4)0.032 (3)0.016 (3)0.008 (2)0.003 (3)
N10.037 (3)0.045 (4)0.029 (3)0.005 (3)0.009 (3)0.006 (3)
N20.064 (5)0.056 (4)0.034 (4)0.004 (4)0.014 (3)0.005 (3)
C10.033 (4)0.039 (4)0.027 (4)0.002 (3)0.004 (3)0.002 (3)
C20.042 (4)0.044 (4)0.028 (4)0.001 (3)0.001 (3)0.006 (3)
C30.039 (4)0.069 (6)0.037 (4)0.006 (4)0.009 (3)0.002 (4)
C40.055 (5)0.051 (5)0.034 (4)0.012 (4)0.005 (4)0.001 (4)
C50.044 (5)0.041 (4)0.034 (4)0.004 (3)0.009 (3)0.003 (3)
C60.037 (4)0.047 (5)0.042 (4)0.002 (3)0.015 (4)0.005 (4)
C70.033 (4)0.060 (5)0.032 (4)0.001 (4)0.006 (3)0.001 (4)
C80.041 (4)0.054 (5)0.037 (4)0.001 (4)0.007 (3)0.006 (4)
C90.034 (4)0.054 (5)0.035 (4)0.002 (3)0.007 (3)0.004 (4)
C100.050 (5)0.062 (6)0.034 (4)0.014 (4)0.004 (4)0.012 (4)
C110.128 (11)0.079 (8)0.078 (8)0.042 (7)0.023 (7)0.010 (6)
C120.091 (8)0.099 (9)0.052 (6)0.030 (7)0.003 (6)0.008 (6)
Geometric parameters (Å, º) top
Zn1—O11.952 (5)C4—H40.9300
Zn1—N12.014 (6)C5—C61.376 (11)
Zn1—Br12.3354 (14)C6—H60.9300
Zn1—Br22.3830 (15)C7—H70.9300
Cl1—C51.748 (8)C8—C91.517 (11)
O1—C21.327 (9)C8—H8A0.9700
N1—C71.254 (10)C8—H8B0.9700
N1—C81.471 (9)C9—C101.509 (11)
N2—C111.462 (12)C9—H9A0.9700
N2—C101.491 (10)C9—H9B0.9700
N2—C121.499 (12)C10—H10A0.9700
N2—H20.89 (6)C10—H10B0.9700
C1—C61.391 (10)C11—H11A0.9600
C1—C21.421 (9)C11—H11B0.9600
C1—C71.447 (10)C11—H11C0.9600
C2—C31.392 (10)C12—H12A0.9600
C3—C41.367 (12)C12—H12B0.9600
C3—H30.9300C12—H12C0.9600
C4—C51.372 (11)
O1—Zn1—N193.8 (2)N1—C7—C1126.4 (7)
O1—Zn1—Br1110.53 (17)N1—C7—H7116.8
N1—Zn1—Br1111.95 (18)C1—C7—H7116.8
O1—Zn1—Br2114.92 (19)N1—C8—C9111.8 (6)
N1—Zn1—Br2108.23 (17)N1—C8—H8A109.3
Br1—Zn1—Br2115.39 (5)C9—C8—H8A109.3
C2—O1—Zn1118.9 (4)N1—C8—H8B109.3
C7—N1—C8119.2 (6)C9—C8—H8B109.3
C7—N1—Zn1119.9 (5)H8A—C8—H8B107.9
C8—N1—Zn1120.8 (5)C10—C9—C8111.8 (7)
C11—N2—C10111.4 (7)C10—C9—H9A109.3
C11—N2—C12110.5 (9)C8—C9—H9A109.3
C10—N2—C12112.8 (7)C10—C9—H9B109.3
C11—N2—H298 (5)C8—C9—H9B109.3
C10—N2—H2106 (5)H9A—C9—H9B107.9
C12—N2—H2117 (5)N2—C10—C9113.1 (6)
C6—C1—C2119.3 (6)N2—C10—H10A109.0
C6—C1—C7116.1 (6)C9—C10—H10A109.0
C2—C1—C7124.5 (7)N2—C10—H10B109.0
O1—C2—C3119.6 (6)C9—C10—H10B109.0
O1—C2—C1123.5 (6)H10A—C10—H10B107.8
C3—C2—C1116.8 (7)N2—C11—H11A109.5
C4—C3—C2123.3 (7)N2—C11—H11B109.5
C4—C3—H3118.4H11A—C11—H11B109.5
C2—C3—H3118.4N2—C11—H11C109.5
C3—C4—C5119.0 (7)H11A—C11—H11C109.5
C3—C4—H4120.5H11B—C11—H11C109.5
C5—C4—H4120.5N2—C12—H12A109.5
C4—C5—C6120.2 (7)N2—C12—H12B109.5
C4—C5—Cl1119.2 (6)H12A—C12—H12B109.5
C6—C5—Cl1120.4 (6)N2—C12—H12C109.5
C5—C6—C1121.1 (7)H12A—C12—H12C109.5
C5—C6—H6119.5H12B—C12—H12C109.5
C1—C6—H6119.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O1i0.89 (6)1.97 (6)2.859 (9)174 (7)
Symmetry code: (i) x1/2, y+3/2, z+1/2.
 

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