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In the title mononuclear zinc(II) complex, [ZnBr2(C13H18Cl2N2O)], there are two independent complex mol­ecules in the asymmetric unit. Each ZnII atom is four-coordinated by the imine N and phenolate O atoms of the Schiff base ligand, and by two Br atoms, forming a tetra­hedral geometry. In the crystal structure, the mol­ecules are linked through inter­molecular N—H...O and C—H...Br hydrogen bonds, forming a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806019222/rz2041sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806019222/rz2041Isup2.hkl
Contains datablock I

CCDC reference: 610882

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.018 Å
  • R factor = 0.066
  • wR factor = 0.130
  • Data-to-parameter ratio = 19.8

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C12 PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for N2 PLAT341_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ... 18
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.06 Ratio PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.77 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.74 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.44 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C9 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C10
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 7708 Count of symmetry unique reflns 4105 Completeness (_total/calc) 187.77% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 3603 Fraction of Friedel pairs measured 0.878 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 3 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 6 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

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Dibromo{2,4-dichloro-6-[2-(diethylamino)ethyliminomethyl]phenolato}zinc(II) top
Crystal data top
[ZnBr2(C13H18Cl2N2O)]F(000) = 1008
Mr = 514.38Dx = 1.912 Mg m3
Monoclinic, PcMo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2ycCell parameters from 2723 reflections
a = 7.687 (1) Åθ = 2.3–25.1°
b = 19.102 (3) ŵ = 6.14 mm1
c = 13.841 (2) ÅT = 298 K
β = 118.452 (3)°Needle, light yellow
V = 1786.9 (4) Å30.12 × 0.07 × 0.06 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
7708 independent reflections
Radiation source: fine-focus sealed tube4594 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.075
ω scansθmax = 27.5°, θmin = 1.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 99
Tmin = 0.515, Tmax = 0.695k = 2324
15186 measured reflectionsl = 1717
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)] = 0.066H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.130 w = 1/[σ2(Fo2)]
S = 0.94(Δ/σ)max < 0.001
7708 reflectionsΔρmax = 0.67 e Å3
389 parametersΔρmin = 0.55 e Å3
4 restraintsAbsolute structure: Flack (1983), 3653 Friedel pairs.
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.007 (13)
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
Zn10.12680 (17)0.39542 (7)0.24197 (10)0.0369 (3)
Zn20.09222 (17)0.10895 (7)0.82759 (10)0.0383 (3)
Br10.18874 (16)0.29897 (6)0.11886 (10)0.0452 (3)
Br20.29188 (19)0.49459 (7)0.13601 (11)0.0584 (4)
Br30.10760 (16)0.01440 (6)0.94171 (9)0.0480 (3)
Br40.06958 (19)0.20750 (7)0.85011 (12)0.0591 (4)
Cl10.3263 (4)0.31079 (17)0.4985 (3)0.0529 (9)
Cl20.4171 (5)0.33573 (19)0.8258 (3)0.0692 (10)
Cl30.3381 (4)0.11551 (16)0.4518 (3)0.0571 (9)
Cl40.2253 (5)0.23369 (16)0.3827 (2)0.0510 (8)
O10.1720 (10)0.3693 (4)0.3616 (6)0.045 (2)
O20.0168 (10)0.0856 (4)0.6706 (6)0.0383 (19)
N10.1607 (11)0.4198 (4)0.3328 (7)0.029 (2)
N20.2025 (13)0.3814 (5)0.1227 (8)0.043 (2)
N30.3650 (12)0.1289 (4)0.8474 (7)0.034 (2)
N40.8008 (13)0.0545 (5)1.1022 (7)0.036 (2)
C10.1666 (16)0.3795 (6)0.5009 (9)0.041 (3)
C20.0337 (16)0.3637 (6)0.4651 (9)0.036 (3)
C30.0790 (15)0.3365 (5)0.5449 (9)0.035 (3)
C40.0501 (18)0.3275 (6)0.6509 (10)0.044 (3)
H40.00870.30940.69900.053*
C50.2477 (16)0.3456 (5)0.6887 (9)0.040 (3)
C60.3043 (16)0.3712 (5)0.6169 (9)0.036 (3)
H60.43590.38400.64280.043*
C70.2491 (16)0.4114 (5)0.4388 (10)0.038 (3)
H70.37840.42770.47780.045*
C80.2743 (17)0.4571 (6)0.2893 (10)0.050 (3)
H8A0.19240.49420.24140.060*
H8B0.38750.47890.35010.060*
C90.344 (2)0.4142 (8)0.2290 (11)0.072 (4)
H9A0.42190.37670.27770.086*
H9B0.43420.44270.21510.086*
C100.291 (2)0.3269 (7)0.0795 (14)0.084 (5)
H10A0.40580.34600.07690.101*
H10B0.19480.31290.00580.101*
C110.353 (2)0.2622 (7)0.1585 (13)0.079 (5)
H11A0.45370.27590.23020.118*
H11B0.40300.22590.13040.118*
H11C0.23980.24510.16330.118*
C120.115 (3)0.4387 (9)0.0368 (14)0.106 (6)
H12A0.07270.47670.06720.127*
H12B0.21900.45680.02280.127*
C130.055 (3)0.4179 (9)0.0700 (12)0.108 (7)
H13A0.01130.38440.10560.161*
H13B0.10620.45850.11600.161*
H13C0.15620.39750.05740.161*
C140.2400 (16)0.1493 (5)0.6516 (9)0.036 (3)
C150.0379 (15)0.1248 (5)0.6090 (9)0.036 (3)
C160.0951 (15)0.1392 (5)0.5018 (10)0.040 (3)
C170.0448 (17)0.1754 (5)0.4317 (9)0.040 (3)
H170.14050.18720.36100.048*
C180.1553 (16)0.1936 (5)0.4706 (9)0.034 (3)
C190.2912 (17)0.1833 (5)0.5790 (9)0.037 (3)
H190.42010.19930.60480.045*
C200.3897 (15)0.1463 (5)0.7657 (9)0.039 (3)
H200.51760.15840.78120.047*
C210.5452 (15)0.1322 (5)0.9568 (8)0.034 (3)
H21A0.51040.14831.01190.041*
H21B0.63970.16490.95440.041*
C220.6348 (16)0.0603 (5)0.9859 (8)0.034 (3)
H22A0.68490.04770.93580.041*
H22B0.53220.02700.97560.041*
C230.9649 (16)0.1040 (6)1.1228 (9)0.044 (3)
H23A0.93620.14901.14440.053*
H23B0.97130.11061.05510.053*
C241.1612 (16)0.0790 (6)1.2100 (9)0.053 (3)
H24A1.15710.07361.27780.080*
H24B1.26120.11261.21970.080*
H24C1.19180.03481.18860.080*
C250.7357 (19)0.0595 (6)1.1861 (9)0.049 (3)
H25A0.66060.10251.17380.058*
H25B0.85210.06321.25750.058*
C260.611 (2)0.0008 (9)1.1893 (13)0.094 (6)
H26A0.48030.00231.12750.141*
H26B0.60160.00141.25610.141*
H26C0.67040.04431.18650.141*
H20.109 (14)0.357 (6)0.130 (11)0.080*
H4A0.834 (18)0.012 (3)1.088 (11)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0265 (7)0.0448 (8)0.0354 (8)0.0015 (6)0.0113 (6)0.0015 (7)
Zn20.0367 (8)0.0421 (8)0.0344 (8)0.0055 (6)0.0155 (6)0.0022 (6)
Br10.0375 (6)0.0428 (7)0.0492 (7)0.0048 (6)0.0157 (6)0.0078 (6)
Br20.0516 (8)0.0532 (8)0.0646 (9)0.0154 (7)0.0230 (7)0.0178 (7)
Br30.0508 (8)0.0538 (8)0.0346 (7)0.0105 (6)0.0164 (6)0.0038 (6)
Br40.0584 (8)0.0504 (8)0.0782 (10)0.0000 (7)0.0404 (8)0.0068 (7)
Cl10.0397 (18)0.068 (2)0.054 (2)0.0071 (16)0.0248 (16)0.0050 (17)
Cl20.063 (2)0.089 (3)0.0340 (18)0.014 (2)0.0055 (17)0.0095 (18)
Cl30.0313 (17)0.054 (2)0.057 (2)0.0087 (15)0.0031 (15)0.0100 (17)
Cl40.0621 (19)0.0555 (19)0.0370 (17)0.0030 (16)0.0249 (15)0.0083 (15)
O10.032 (4)0.060 (5)0.034 (5)0.006 (4)0.009 (4)0.008 (4)
O20.037 (4)0.043 (5)0.032 (4)0.012 (4)0.014 (4)0.005 (4)
N10.024 (5)0.035 (5)0.027 (5)0.003 (4)0.011 (4)0.001 (4)
N20.034 (5)0.046 (6)0.042 (6)0.004 (5)0.012 (5)0.013 (5)
N30.039 (5)0.026 (5)0.031 (5)0.006 (4)0.013 (4)0.005 (4)
N40.033 (5)0.047 (6)0.024 (5)0.002 (5)0.012 (4)0.006 (5)
C10.034 (7)0.036 (7)0.040 (7)0.005 (5)0.006 (6)0.003 (6)
C20.038 (7)0.042 (7)0.032 (7)0.005 (5)0.018 (6)0.007 (5)
C30.027 (6)0.033 (6)0.050 (8)0.003 (5)0.023 (6)0.005 (5)
C40.053 (8)0.050 (8)0.034 (7)0.003 (6)0.024 (6)0.003 (6)
C50.040 (7)0.039 (7)0.030 (6)0.007 (5)0.006 (5)0.011 (5)
C60.031 (6)0.041 (6)0.024 (6)0.010 (5)0.003 (5)0.004 (5)
C70.031 (6)0.033 (7)0.052 (8)0.004 (5)0.022 (6)0.001 (6)
C80.043 (8)0.050 (8)0.046 (8)0.007 (6)0.013 (6)0.000 (6)
C90.059 (9)0.109 (12)0.047 (9)0.032 (9)0.026 (8)0.009 (9)
C100.088 (12)0.075 (11)0.120 (15)0.014 (9)0.074 (12)0.017 (10)
C110.081 (11)0.067 (10)0.104 (13)0.010 (9)0.056 (10)0.011 (9)
C120.108 (14)0.114 (15)0.104 (15)0.003 (12)0.057 (13)0.045 (12)
C130.103 (14)0.129 (16)0.035 (9)0.035 (12)0.012 (9)0.015 (10)
C140.038 (7)0.042 (7)0.030 (6)0.003 (5)0.017 (5)0.002 (5)
C150.031 (6)0.028 (6)0.037 (7)0.007 (5)0.005 (5)0.011 (5)
C160.033 (6)0.028 (6)0.061 (8)0.003 (5)0.024 (6)0.003 (6)
C170.044 (7)0.032 (6)0.031 (7)0.001 (5)0.008 (6)0.001 (5)
C180.038 (6)0.033 (6)0.030 (6)0.001 (5)0.016 (5)0.006 (5)
C190.035 (6)0.033 (6)0.043 (7)0.001 (5)0.019 (6)0.003 (5)
C200.029 (6)0.041 (7)0.040 (7)0.002 (5)0.010 (6)0.007 (5)
C210.027 (6)0.036 (6)0.033 (6)0.002 (5)0.009 (5)0.004 (5)
C220.039 (6)0.031 (6)0.034 (7)0.003 (5)0.018 (5)0.003 (5)
C230.045 (7)0.048 (8)0.035 (7)0.012 (6)0.015 (6)0.002 (6)
C240.044 (8)0.059 (9)0.042 (8)0.004 (6)0.009 (6)0.003 (7)
C250.064 (8)0.061 (9)0.022 (6)0.013 (7)0.021 (6)0.008 (6)
C260.054 (9)0.149 (16)0.088 (12)0.039 (10)0.042 (9)0.049 (11)
Geometric parameters (Å, º) top
Zn1—O11.913 (7)C9—H9B0.9700
Zn1—N12.009 (8)C10—C111.567 (19)
Zn1—Br22.3616 (18)C10—H10A0.9700
Zn1—Br12.3982 (17)C10—H10B0.9700
Zn2—O21.972 (7)C11—H11A0.9600
Zn2—N32.017 (8)C11—H11B0.9600
Zn2—Br42.3575 (18)C11—H11C0.9600
Zn2—Br32.3649 (17)C12—C131.49 (2)
Cl1—C31.762 (10)C12—H12A0.9700
Cl2—C51.725 (11)C12—H12B0.9700
Cl3—C161.715 (11)C13—H13A0.9600
Cl4—C181.726 (10)C13—H13B0.9600
O1—C21.321 (12)C13—H13C0.9600
O2—C151.343 (12)C14—C191.401 (14)
N1—C71.300 (13)C14—C201.445 (14)
N1—C81.460 (13)C14—C151.451 (14)
N2—C91.489 (15)C15—C161.370 (15)
N2—C101.514 (16)C16—C171.387 (15)
N2—C121.517 (17)C17—C181.410 (14)
N2—H20.90 (12)C17—H170.9300
N3—C201.278 (12)C18—C191.374 (14)
N3—C211.489 (12)C19—H190.9300
N4—C251.469 (13)C20—H200.9300
N4—C231.491 (13)C21—C221.503 (13)
N4—C221.508 (13)C21—H21A0.9700
N4—H4A0.90 (9)C21—H21B0.9700
C1—C21.407 (14)C22—H22A0.9700
C1—C71.426 (15)C22—H22B0.9700
C1—C61.450 (14)C23—C241.492 (15)
C2—C31.406 (14)C23—H23A0.9700
C3—C41.334 (15)C23—H23B0.9700
C4—C51.394 (15)C24—H24A0.9600
C4—H40.9300C24—H24B0.9600
C5—C61.353 (14)C24—H24C0.9600
C6—H60.9300C25—C261.516 (18)
C7—H70.9300C25—H25A0.9700
C8—C91.442 (16)C25—H25B0.9700
C8—H8A0.9700C26—H26A0.9600
C8—H8B0.9700C26—H26B0.9600
C9—H9A0.9700C26—H26C0.9600
O1—Zn1—N196.8 (3)H11A—C11—H11B109.5
O1—Zn1—Br2118.8 (2)C10—C11—H11C109.5
N1—Zn1—Br2107.9 (2)H11A—C11—H11C109.5
O1—Zn1—Br1111.0 (2)H11B—C11—H11C109.5
N1—Zn1—Br1114.2 (2)C13—C12—N2116.0 (14)
Br2—Zn1—Br1107.99 (7)C13—C12—H12A108.3
O2—Zn2—N393.5 (3)N2—C12—H12A108.3
O2—Zn2—Br4110.6 (2)C13—C12—H12B108.3
N3—Zn2—Br4114.3 (2)N2—C12—H12B108.3
O2—Zn2—Br3115.1 (2)H12A—C12—H12B107.4
N3—Zn2—Br3109.6 (2)C12—C13—H13A109.5
Br4—Zn2—Br3112.53 (7)C12—C13—H13B109.5
C2—O1—Zn1125.2 (7)H13A—C13—H13B109.5
C15—O2—Zn2118.4 (6)C12—C13—H13C109.5
C7—N1—C8115.6 (9)H13A—C13—H13C109.5
C7—N1—Zn1120.4 (7)H13B—C13—H13C109.5
C8—N1—Zn1123.4 (7)C19—C14—C20116.9 (10)
C9—N2—C10115.2 (11)C19—C14—C15118.0 (10)
C9—N2—C12108.3 (11)C20—C14—C15124.9 (10)
C10—N2—C12107.5 (11)O2—C15—C16120.1 (10)
C9—N2—H2111 (9)O2—C15—C14121.3 (9)
C10—N2—H2103 (8)C16—C15—C14118.5 (11)
C12—N2—H2112 (8)C15—C16—C17123.0 (10)
C20—N3—C21115.5 (9)C15—C16—Cl3119.4 (9)
C20—N3—Zn2120.8 (7)C17—C16—Cl3117.5 (9)
C21—N3—Zn2123.3 (7)C16—C17—C18118.2 (10)
C25—N4—C23112.5 (9)C16—C17—H17120.9
C25—N4—C22113.9 (9)C18—C17—H17120.9
C23—N4—C22111.5 (8)C19—C18—C17120.3 (10)
C25—N4—H4A118 (9)C19—C18—Cl4120.2 (9)
C23—N4—H4A108 (8)C17—C18—Cl4119.4 (8)
C22—N4—H4A91 (9)C18—C19—C14121.5 (11)
C2—C1—C7127.3 (10)C18—C19—H19119.3
C2—C1—C6117.8 (11)C14—C19—H19119.3
C7—C1—C6114.5 (10)N3—C20—C14126.9 (10)
O1—C2—C3120.7 (10)N3—C20—H20116.5
O1—C2—C1123.0 (10)C14—C20—H20116.5
C3—C2—C1116.2 (10)N3—C21—C22108.6 (8)
C4—C3—C2125.3 (10)N3—C21—H21A110.0
C4—C3—Cl1118.3 (9)C22—C21—H21A110.0
C2—C3—Cl1116.4 (9)N3—C21—H21B110.0
C3—C4—C5119.2 (11)C22—C21—H21B110.0
C3—C4—H4120.4H21A—C21—H21B108.4
C5—C4—H4120.4C21—C22—N4113.5 (8)
C6—C5—C4119.2 (10)C21—C22—H22A108.9
C6—C5—Cl2120.6 (9)N4—C22—H22A108.9
C4—C5—Cl2120.2 (9)C21—C22—H22B108.9
C5—C6—C1122.1 (10)N4—C22—H22B108.9
C5—C6—H6118.9H22A—C22—H22B107.7
C1—C6—H6118.9N4—C23—C24113.0 (9)
N1—C7—C1126.2 (10)N4—C23—H23A109.0
N1—C7—H7116.9C24—C23—H23A109.0
C1—C7—H7116.9N4—C23—H23B109.0
C9—C8—N1114.9 (10)C24—C23—H23B109.0
C9—C8—H8A108.5H23A—C23—H23B107.8
N1—C8—H8A108.5C23—C24—H24A109.5
C9—C8—H8B108.5C23—C24—H24B109.5
N1—C8—H8B108.5H24A—C24—H24B109.5
H8A—C8—H8B107.5C23—C24—H24C109.5
C8—C9—N2120.9 (11)H24A—C24—H24C109.5
C8—C9—H9A107.1H24B—C24—H24C109.5
N2—C9—H9A107.1N4—C25—C26115.7 (11)
C8—C9—H9B107.1N4—C25—H25A108.4
N2—C9—H9B107.1C26—C25—H25A108.4
H9A—C9—H9B106.8N4—C25—H25B108.4
N2—C10—C11108.1 (11)C26—C25—H25B108.4
N2—C10—H10A110.1H25A—C25—H25B107.4
C11—C10—H10A110.1C25—C26—H26A109.5
N2—C10—H10B110.1C25—C26—H26B109.5
C11—C10—H10B110.1H26A—C26—H26B109.5
H10A—C10—H10B108.4C25—C26—H26C109.5
C10—C11—H11A109.5H26A—C26—H26C109.5
C10—C11—H11B109.5H26B—C26—H26C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4A···O2i0.90 (9)2.20 (8)2.960 (11)142 (11)
N2—H2···Br10.90 (12)2.48 (13)3.373 (9)170 (11)
C7—H7···Br2ii0.932.853.735 (8)159
C23—H23B···Br3iii0.972.923.611 (8)129
C25—H25B···Br3i0.972.793.613 (8)143
C26—H26A···Br30.962.803.764 (17)177
Symmetry codes: (i) x+1, y, z+1/2; (ii) x+1, y+1, z+1/2; (iii) x+1, y, z.
 

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