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The title compound, [ZnBr2(C13H19ClN2O)], 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 bromide anions in a tetra­hedral geometry. In the crystal structure, mol­ecules are linked through inter­molecular N—H...O and C—H...Br hydrogen bonds, forming layers parallel to the bc plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807004564/hg2179sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807004564/hg2179Isup2.hkl
Contains datablock I

CCDC reference: 640357

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.043
  • wR factor = 0.113
  • Data-to-parameter ratio = 21.4

checkCIF/PLATON results

No syntax errors found



Alert level C CELLV02_ALERT_1_C The supplied cell volume s.u. differs from that calculated from the cell parameter s.u.'s by > 2 Calculated cell volume su = 2.92 Cell volume su given = 6.00 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.77 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3 PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Br2 - Zn1 .. 8.98 su
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 0.769 Tmax scaled 0.276 Tmin scaled 0.256
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 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, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Dibromo{4-chloro-2-[(2-diethylaminoethylimino)methyl]phenolato}zinc(II) top
Crystal data top
[ZnBr2(C13H19ClN2O)]F(000) = 944
Mr = 479.94Dx = 1.823 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2913 reflections
a = 14.921 (1) Åθ = 2.6–25.7°
b = 8.9624 (1) ŵ = 6.12 mm1
c = 13.092 (2) ÅT = 298 K
β = 92.600 (1)°Block, colourless
V = 1749.0 (6) Å30.23 × 0.21 × 0.21 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
4008 independent reflections
Radiation source: fine-focus sealed tube2754 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
ω scansθmax = 27.5°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1719
Tmin = 0.333, Tmax = 0.360k = 911
10219 measured reflectionsl = 1713
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0591P)2]
where P = (Fo2 + 2Fc2)/3
4008 reflections(Δ/σ)max < 0.001
187 parametersΔρmax = 0.89 e Å3
1 restraintΔρmin = 0.67 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
Zn10.22962 (3)0.23841 (5)0.08799 (3)0.03693 (15)
Br10.24699 (4)0.44459 (5)0.19705 (4)0.06443 (19)
Br20.07924 (4)0.18373 (6)0.05244 (4)0.06643 (19)
Cl10.51403 (10)0.33621 (13)0.13599 (10)0.0644 (4)
O10.28871 (19)0.0540 (3)0.12930 (19)0.0370 (7)
N10.3032 (2)0.2648 (3)0.0440 (2)0.0330 (7)
N20.1832 (2)0.5518 (3)0.1994 (2)0.0330 (7)
C10.3717 (3)0.0181 (4)0.0320 (3)0.0301 (8)
C20.3414 (3)0.0274 (4)0.0673 (3)0.0311 (8)
C30.3680 (3)0.1692 (4)0.0999 (3)0.0393 (10)
H30.35000.20090.16530.047*
C40.4196 (3)0.2627 (4)0.0387 (3)0.0420 (10)
H40.43610.35590.06280.050*
C50.4471 (3)0.2182 (4)0.0587 (3)0.0405 (10)
C60.4254 (3)0.0804 (4)0.0934 (3)0.0352 (9)
H60.44600.05050.15830.042*
C70.3547 (3)0.1612 (4)0.0789 (3)0.0325 (8)
H70.38480.17970.14140.039*
C80.2966 (3)0.4013 (4)0.1050 (3)0.0386 (9)
H8A0.31740.48630.06700.046*
H8B0.33330.39250.16780.046*
C90.1987 (3)0.4224 (4)0.1294 (3)0.0351 (9)
H9A0.16370.43740.06600.042*
H9B0.17730.33200.16090.042*
C100.2195 (3)0.6981 (4)0.1604 (3)0.0406 (10)
H10A0.21030.77520.21090.049*
H10B0.28360.68820.15300.049*
C110.1764 (4)0.7467 (5)0.0598 (4)0.0593 (13)
H11A0.18240.66890.01010.089*
H11B0.20540.83550.03690.089*
H11C0.11400.76680.06810.089*
C120.0857 (3)0.5592 (4)0.2221 (3)0.0429 (10)
H12A0.06690.46250.24660.051*
H12B0.05120.58020.15920.051*
C130.0647 (4)0.6762 (6)0.3005 (4)0.0689 (15)
H13A0.10260.66170.36090.103*
H13B0.00300.66760.31750.103*
H13C0.07510.77350.27290.103*
H20.216 (2)0.529 (4)0.2572 (19)0.035 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0493 (3)0.0314 (2)0.0295 (2)0.00799 (19)0.0044 (2)0.00309 (18)
Br10.1017 (5)0.0405 (3)0.0513 (3)0.0169 (2)0.0062 (3)0.0144 (2)
Br20.0464 (3)0.0854 (4)0.0673 (3)0.0053 (3)0.0012 (2)0.0276 (3)
Cl10.0789 (10)0.0502 (7)0.0624 (8)0.0257 (6)0.0168 (7)0.0073 (6)
O10.0523 (19)0.0307 (13)0.0273 (13)0.0088 (12)0.0062 (12)0.0052 (10)
N10.043 (2)0.0278 (16)0.0285 (15)0.0025 (13)0.0018 (14)0.0047 (12)
N20.045 (2)0.0274 (15)0.0256 (15)0.0017 (13)0.0039 (14)0.0034 (12)
C10.031 (2)0.0302 (18)0.0294 (18)0.0021 (15)0.0025 (15)0.0013 (14)
C20.035 (2)0.0276 (19)0.0305 (19)0.0008 (15)0.0027 (16)0.0011 (15)
C30.046 (3)0.037 (2)0.034 (2)0.0075 (18)0.0022 (18)0.0070 (17)
C40.047 (3)0.029 (2)0.050 (2)0.0075 (17)0.000 (2)0.0067 (17)
C50.043 (3)0.032 (2)0.046 (2)0.0071 (17)0.0035 (19)0.0094 (17)
C60.036 (2)0.039 (2)0.0310 (19)0.0025 (16)0.0025 (16)0.0006 (16)
C70.034 (2)0.037 (2)0.0263 (18)0.0048 (16)0.0000 (15)0.0037 (15)
C80.052 (3)0.0297 (19)0.034 (2)0.0008 (17)0.0032 (18)0.0066 (16)
C90.050 (3)0.0247 (18)0.0301 (19)0.0002 (16)0.0018 (17)0.0071 (14)
C100.049 (3)0.0239 (18)0.049 (2)0.0031 (16)0.002 (2)0.0028 (16)
C110.059 (4)0.053 (3)0.066 (3)0.002 (2)0.004 (3)0.028 (2)
C120.052 (3)0.041 (2)0.036 (2)0.0006 (19)0.0072 (19)0.0003 (17)
C130.086 (4)0.064 (3)0.059 (3)0.014 (3)0.026 (3)0.010 (3)
Geometric parameters (Å, º) top
Zn1—O11.961 (2)C5—C61.360 (5)
Zn1—N12.018 (3)C6—H60.9300
Zn1—Br12.3567 (7)C7—H70.9300
Zn1—Br22.3636 (9)C8—C91.520 (6)
Cl1—C51.746 (4)C8—H8A0.9700
O1—C21.323 (4)C8—H8B0.9700
N1—C71.277 (5)C9—H9A0.9700
N1—C81.466 (4)C9—H9B0.9700
N2—C121.500 (6)C10—C111.504 (6)
N2—C91.503 (4)C10—H10A0.9700
N2—C101.516 (5)C10—H10B0.9700
N2—H20.91 (3)C11—H11A0.9600
C1—C21.417 (5)C11—H11B0.9600
C1—C61.417 (5)C11—H11C0.9600
C1—C71.449 (5)C12—C131.510 (6)
C2—C31.404 (5)C12—H12A0.9700
C3—C41.372 (5)C12—H12B0.9700
C3—H30.9300C13—H13A0.9600
C4—C51.380 (6)C13—H13B0.9600
C4—H40.9300C13—H13C0.9600
O1—Zn1—N195.81 (11)N1—C8—C9107.9 (3)
O1—Zn1—Br1115.51 (9)N1—C8—H8A110.1
N1—Zn1—Br1110.86 (9)C9—C8—H8A110.1
O1—Zn1—Br2108.80 (9)N1—C8—H8B110.1
N1—Zn1—Br2109.88 (10)C9—C8—H8B110.1
Br1—Zn1—Br2114.41 (3)H8A—C8—H8B108.4
C2—O1—Zn1123.9 (2)N2—C9—C8113.6 (3)
C7—N1—C8117.8 (3)N2—C9—H9A108.9
C7—N1—Zn1121.1 (2)C8—C9—H9A108.9
C8—N1—Zn1121.1 (2)N2—C9—H9B108.9
C12—N2—C9109.4 (3)C8—C9—H9B108.9
C12—N2—C10113.1 (3)H9A—C9—H9B107.7
C9—N2—C10113.3 (3)C11—C10—N2113.7 (3)
C12—N2—H2110 (3)C11—C10—H10A108.8
C9—N2—H2104 (2)N2—C10—H10A108.8
C10—N2—H2107 (2)C11—C10—H10B108.8
C2—C1—C6119.3 (3)N2—C10—H10B108.8
C2—C1—C7126.0 (3)H10A—C10—H10B107.7
C6—C1—C7114.6 (3)C10—C11—H11A109.5
O1—C2—C3118.7 (3)C10—C11—H11B109.5
O1—C2—C1124.1 (3)H11A—C11—H11B109.5
C3—C2—C1117.2 (3)C10—C11—H11C109.5
C4—C3—C2122.3 (4)H11A—C11—H11C109.5
C4—C3—H3118.8H11B—C11—H11C109.5
C2—C3—H3118.8N2—C12—C13113.5 (4)
C3—C4—C5119.9 (3)N2—C12—H12A108.9
C3—C4—H4120.0C13—C12—H12A108.9
C5—C4—H4120.0N2—C12—H12B108.9
C6—C5—C4120.4 (3)C13—C12—H12B108.9
C6—C5—Cl1119.7 (3)H12A—C12—H12B107.7
C4—C5—Cl1119.9 (3)C12—C13—H13A109.5
C5—C6—C1120.9 (3)C12—C13—H13B109.5
C5—C6—H6119.6H13A—C13—H13B109.5
C1—C6—H6119.6C12—C13—H13C109.5
N1—C7—C1127.3 (3)H13A—C13—H13C109.5
N1—C7—H7116.3H13B—C13—H13C109.5
C1—C7—H7116.3
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O1i0.91 (3)1.95 (3)2.843 (4)170 (3)
C10—H10A···Br1ii0.972.833.719 (4)153
C11—H11C···Br2iii0.962.913.862 (4)169
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x, y+3/2, z+1/2; (iii) x, y+1, z.
 

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