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The title complex, [Zn(C11H14Cl2N2O)Cl2], is a mononuclear zinc(II) compound. The ZnII atom is four-coordinated in a tetra­hedral configuration by one imine N and one phenolate O atoms of a Schiff base ligand, and by two Cl atoms. The mol­ecules are linked through inter­molecular N—H...Cl, C—H...O, and C—H...Cl hydrogen bonds, forming a three-dimensional framework.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805034744/ci6681sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805034744/ci6681Isup2.hkl
Contains datablock I

CCDC reference: 289701

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.051
  • wR factor = 0.098
  • Data-to-parameter ratio = 20.5

checkCIF/PLATON results

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Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.50 From the CIF: _reflns_number_total 3622 Count of symmetry unique reflns 2098 Completeness (_total/calc) 172.64% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1524 Fraction of Friedel pairs measured 0.726 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 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 0 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 1 ALERT type 4 Improvement, methodology, query or suggestion

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.

Dichloro{2,4-dichloro-6-[2-(dimethylamino)ethyliminomethyl]phenolato}zinc(II) top
Crystal data top
[Zn(C11H14Cl2N2O)Cl2]F(000) = 800
Mr = 397.41Dx = 1.667 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 3029 reflections
a = 7.728 (1) Åθ = 2.2–23.0°
b = 10.127 (1) ŵ = 2.22 mm1
c = 20.237 (2) ÅT = 298 K
V = 1583.8 (3) Å3Needle, colourless
Z = 40.17 × 0.14 × 0.06 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
3622 independent reflections
Radiation source: fine-focus sealed tube3137 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.049
ω scansθmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 910
Tmin = 0.704, Tmax = 0.879k = 1213
13624 measured reflectionsl = 2526
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.098 w = 1/[σ2(Fo2) + (0.0355P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.14(Δ/σ)max = 0.001
3622 reflectionsΔρmax = 0.54 e Å3
177 parametersΔρmin = 0.42 e Å3
1 restraintAbsolute structure: Flack (1983), 1526 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.025 (17)
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
Zn10.43782 (7)0.42342 (5)0.57097 (2)0.03842 (15)
Cl10.3782 (2)0.28554 (12)0.48689 (6)0.0563 (4)
Cl20.23799 (16)0.58397 (12)0.56925 (6)0.0520 (3)
Cl30.5082 (2)0.14071 (15)0.76038 (7)0.0694 (4)
Cl41.1427 (2)0.3322 (2)0.80158 (8)0.0815 (5)
O10.4975 (4)0.3245 (3)0.64897 (15)0.0440 (8)
N10.6672 (5)0.5179 (3)0.56449 (18)0.0361 (8)
N20.7585 (5)0.4561 (3)0.4232 (2)0.0435 (9)
C10.7873 (6)0.4093 (4)0.6627 (2)0.0377 (10)
C20.6450 (6)0.3280 (4)0.6799 (2)0.0358 (10)
C30.6730 (7)0.2475 (5)0.7363 (2)0.0450 (12)
C40.8207 (6)0.2481 (5)0.7725 (2)0.0456 (13)
H40.83090.19420.80950.055*
C50.9556 (6)0.3291 (5)0.7541 (2)0.0469 (12)
C60.9404 (6)0.4078 (5)0.6999 (2)0.0461 (11)
H61.03260.46130.68740.055*
C70.7887 (6)0.4995 (4)0.6067 (2)0.0387 (11)
H70.88860.54940.60090.046*
C80.6954 (7)0.6189 (4)0.5143 (2)0.0440 (12)
H8A0.81580.64600.51500.053*
H8B0.62500.69560.52440.053*
C90.6502 (7)0.5693 (4)0.4462 (2)0.0436 (11)
H9A0.52980.54230.44600.052*
H9B0.66250.64140.41500.052*
C100.9432 (7)0.4924 (6)0.4128 (3)0.0658 (16)
H10A1.00680.41600.39880.099*
H10B0.99110.52520.45340.099*
H10C0.95070.55960.37940.099*
C110.6831 (7)0.3956 (5)0.3632 (2)0.0546 (14)
H11A0.56810.36530.37270.082*
H11B0.75340.32240.34960.082*
H11C0.67900.46010.32850.082*
H20.765 (8)0.393 (4)0.4545 (19)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0431 (3)0.0341 (3)0.0380 (3)0.0016 (3)0.0008 (3)0.0054 (3)
Cl10.0782 (10)0.0443 (7)0.0465 (7)0.0141 (7)0.0001 (7)0.0046 (6)
Cl20.0573 (7)0.0468 (6)0.0520 (7)0.0130 (6)0.0033 (6)0.0016 (7)
Cl30.0726 (10)0.0736 (10)0.0621 (9)0.0174 (8)0.0051 (7)0.0341 (7)
Cl40.0540 (9)0.1210 (14)0.0696 (10)0.0110 (10)0.0161 (8)0.0101 (10)
O10.047 (2)0.0442 (18)0.0406 (17)0.0090 (16)0.0046 (16)0.0151 (15)
N10.044 (2)0.0264 (18)0.038 (2)0.0010 (16)0.0066 (19)0.0002 (17)
N20.053 (2)0.035 (2)0.043 (2)0.0034 (18)0.002 (2)0.0089 (18)
C10.048 (3)0.032 (2)0.033 (2)0.005 (2)0.004 (2)0.001 (2)
C20.048 (3)0.029 (2)0.030 (2)0.006 (2)0.006 (2)0.0005 (18)
C30.052 (3)0.043 (3)0.040 (3)0.003 (2)0.004 (2)0.005 (2)
C40.050 (3)0.053 (3)0.033 (3)0.012 (3)0.000 (2)0.006 (2)
C50.045 (3)0.057 (3)0.039 (2)0.012 (3)0.001 (2)0.004 (2)
C60.043 (3)0.056 (3)0.039 (2)0.001 (3)0.001 (2)0.001 (2)
C70.039 (3)0.032 (2)0.045 (3)0.007 (2)0.008 (2)0.003 (2)
C80.063 (3)0.024 (2)0.045 (3)0.004 (2)0.004 (2)0.007 (2)
C90.058 (3)0.033 (2)0.040 (3)0.009 (3)0.000 (2)0.013 (2)
C100.058 (4)0.066 (4)0.074 (4)0.003 (3)0.012 (3)0.008 (3)
C110.071 (4)0.051 (3)0.042 (3)0.005 (3)0.004 (3)0.002 (2)
Geometric parameters (Å, º) top
Zn1—O11.926 (3)C3—C41.356 (6)
Zn1—N12.019 (4)C4—C51.378 (7)
Zn1—Cl22.2427 (13)C4—H40.93
Zn1—Cl12.2487 (14)C5—C61.361 (6)
Cl3—C31.741 (5)C6—H60.93
Cl4—C51.736 (5)C7—H70.93
O1—C21.300 (5)C8—C91.507 (6)
N1—C71.283 (6)C8—H8A0.97
N1—C81.458 (5)C8—H8B0.97
N2—C111.479 (6)C9—H9A0.97
N2—C101.489 (7)C9—H9B0.97
N2—C91.493 (6)C10—H10A0.96
N2—H20.90 (4)C10—H10B0.96
C1—C61.402 (6)C10—H10C0.96
C1—C21.417 (6)C11—H11A0.96
C1—C71.456 (6)C11—H11B0.96
C2—C31.419 (6)C11—H11C0.96
O1—Zn1—N195.13 (14)C5—C6—C1120.7 (5)
O1—Zn1—Cl2123.71 (10)C5—C6—H6119.6
N1—Zn1—Cl2105.07 (11)C1—C6—H6119.6
O1—Zn1—Cl1110.26 (10)N1—C7—C1127.2 (4)
N1—Zn1—Cl1115.15 (11)N1—C7—H7116.4
Cl2—Zn1—Cl1107.31 (5)C1—C7—H7116.4
C2—O1—Zn1126.2 (3)N1—C8—C9111.6 (4)
C7—N1—C8117.2 (4)N1—C8—H8A109.3
C7—N1—Zn1122.0 (3)C9—C8—H8A109.3
C8—N1—Zn1120.6 (3)N1—C8—H8B109.3
C11—N2—C10111.3 (4)C9—C8—H8B109.3
C11—N2—C9110.7 (4)H8A—C8—H8B108.0
C10—N2—C9113.0 (4)N2—C9—C8114.3 (4)
C11—N2—H2108 (4)N2—C9—H9A108.7
C10—N2—H2103 (4)C8—C9—H9A108.7
C9—N2—H2111 (4)N2—C9—H9B108.7
C6—C1—C2121.2 (4)C8—C9—H9B108.7
C6—C1—C7114.7 (4)H9A—C9—H9B107.6
C2—C1—C7124.1 (4)N2—C10—H10A109.5
O1—C2—C1125.3 (4)N2—C10—H10B109.5
O1—C2—C3120.3 (4)H10A—C10—H10B109.5
C1—C2—C3114.4 (4)N2—C10—H10C109.5
C4—C3—C2124.1 (5)H10A—C10—H10C109.5
C4—C3—Cl3117.8 (4)H10B—C10—H10C109.5
C2—C3—Cl3118.1 (4)N2—C11—H11A109.5
C3—C4—C5119.6 (4)N2—C11—H11B109.5
C3—C4—H4120.2H11A—C11—H11B109.5
C5—C4—H4120.2N2—C11—H11C109.5
C6—C5—C4120.1 (5)H11A—C11—H11C109.5
C6—C5—Cl4120.5 (4)H11B—C11—H11C109.5
C4—C5—Cl4119.4 (4)
N1—Zn1—O1—C21.1 (4)C1—C2—C3—Cl3178.4 (3)
Cl2—Zn1—O1—C2113.1 (3)C2—C3—C4—C51.2 (8)
Cl1—Zn1—O1—C2118.1 (3)Cl3—C3—C4—C5178.6 (4)
O1—Zn1—N1—C70.9 (4)C3—C4—C5—C60.0 (7)
Cl2—Zn1—N1—C7126.0 (3)C3—C4—C5—Cl4178.6 (4)
Cl1—Zn1—N1—C7116.2 (3)C4—C5—C6—C10.9 (7)
O1—Zn1—N1—C8175.6 (3)Cl4—C5—C6—C1177.7 (4)
Cl2—Zn1—N1—C848.7 (3)C2—C1—C6—C50.7 (7)
Cl1—Zn1—N1—C869.2 (3)C7—C1—C6—C5179.2 (4)
Zn1—O1—C2—C12.1 (6)C8—N1—C7—C1177.0 (4)
Zn1—O1—C2—C3178.6 (3)Zn1—N1—C7—C12.2 (6)
C6—C1—C2—O1178.9 (4)C6—C1—C7—N1178.7 (4)
C7—C1—C2—O11.0 (7)C2—C1—C7—N11.4 (7)
C6—C1—C2—C30.4 (6)C7—N1—C8—C9132.8 (4)
C7—C1—C2—C3179.7 (4)Zn1—N1—C8—C952.3 (5)
O1—C2—C3—C4177.9 (4)C11—N2—C9—C8168.0 (4)
C1—C2—C3—C41.4 (7)C10—N2—C9—C866.4 (5)
O1—C2—C3—Cl32.3 (6)N1—C8—C9—N262.7 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···Cl1i0.90 (4)2.33 (2)3.186 (4)158 (5)
C4—H4···Cl2ii0.932.753.637 (4)160
C7—H7···Cl2iii0.932.803.655 (4)154
C11—H11B···O1i0.962.403.307 (4)157
Symmetry codes: (i) x+1/2, y+1/2, z+1; (ii) x+1, y1/2, z+3/2; (iii) x+1, y, z.
 

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