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In the title ZnII complex, [ZnCl2(C11H15N5O)], the Zn atom is coordinated by two Cl atoms and two imidazole N atoms in a distorted tetra­hedral geometry. Weak inter­molecular C—H...O hydrogen bonding occurs between imidazole and aldehyde groups.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806036543/sg2058sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806036543/sg2058Isup2.hkl
Contains datablock I

CCDC reference: 628387

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • R factor = 0.043
  • wR factor = 0.115
  • Data-to-parameter ratio = 17.7

checkCIF/PLATON results

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No errors found in this datablock

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); 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, 1998); software used to prepare material for publication: SHELXTL.

{N,N-Bis[(1-methylimidazole-2-yl)methyl]formamide}dichlorozinc(II) top
Crystal data top
[ZnCl2(C11H15N5O)]F(000) = 752
Mr = 369.57Dx = 1.633 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2728 reflections
a = 12.4750 (11) Åθ = 5.5–48.9°
b = 8.0615 (7) ŵ = 1.99 mm1
c = 15.1166 (13) ÅT = 298 K
β = 98.690 (2)°Block, colorless
V = 1502.8 (2) Å30.32 × 0.22 × 0.16 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
3246 independent reflections
Radiation source: fine-focus sealed tube2396 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.050
φ and ω scansθmax = 27.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
h = 1315
Tmin = 0.589, Tmax = 0.730k = 1010
8537 measured reflectionsl = 1919
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) = 0.115H-atom parameters constrained
S = 0.96 w = 1/[σ2(Fo2) + (0.0644P)2]
where P = (Fo2 + 2Fc2)/3
3246 reflections(Δ/σ)max < 0.001
183 parametersΔρmax = 0.94 e Å3
0 restraintsΔρmin = 0.56 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
Zn0.27106 (3)0.34375 (5)0.59980 (2)0.04870 (16)
Cl10.35853 (7)0.09955 (11)0.60157 (6)0.0592 (2)
Cl20.27325 (8)0.48418 (12)0.72662 (6)0.0656 (3)
O10.0645 (4)0.3770 (4)0.2864 (2)0.1098 (12)
N10.1160 (2)0.2971 (3)0.54655 (17)0.0502 (6)
N20.0305 (2)0.2124 (3)0.45980 (18)0.0534 (7)
N30.2031 (2)0.2952 (3)0.36516 (18)0.0483 (6)
N40.3353 (2)0.5011 (3)0.51739 (17)0.0459 (6)
N50.3881 (2)0.6135 (3)0.39937 (17)0.0460 (6)
C10.0774 (2)0.2232 (4)0.4695 (2)0.0472 (7)
C20.0277 (3)0.3335 (4)0.5869 (2)0.0567 (9)
H20.02980.38600.64190.068*
C30.0624 (3)0.2813 (5)0.5344 (2)0.0612 (9)
H30.13310.29020.54650.073*
C40.1472 (3)0.1601 (4)0.4049 (2)0.0531 (8)
H4A0.20060.08410.43550.064*
H4B0.10260.09920.35760.064*
C50.1026 (3)0.1460 (5)0.3834 (3)0.0696 (11)
H5A0.11380.22790.33690.104*
H5B0.17090.11750.40130.104*
H5C0.07060.04870.36170.104*
C60.3481 (2)0.4767 (4)0.4335 (2)0.0432 (7)
C70.3673 (3)0.6607 (4)0.5373 (2)0.0494 (8)
H70.36670.71230.59230.059*
C80.3997 (2)0.7316 (4)0.4656 (2)0.0518 (8)
H80.42510.83940.46150.062*
C90.3192 (3)0.3200 (4)0.3829 (2)0.0503 (8)
H9A0.34760.32380.32660.060*
H9B0.35260.22680.41710.060*
C100.4145 (3)0.6345 (5)0.3086 (2)0.0634 (10)
H10A0.47050.55760.29930.095*
H10B0.43940.74580.30160.095*
H10C0.35100.61400.26570.095*
C110.1547 (3)0.4036 (6)0.3045 (2)0.0644 (11)
H110.19050.48980.28030.077*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn0.0564 (3)0.0441 (3)0.0457 (2)0.00590 (16)0.00793 (18)0.00049 (16)
Cl10.0589 (5)0.0442 (5)0.0744 (6)0.0023 (4)0.0097 (4)0.0060 (4)
Cl20.0960 (7)0.0553 (6)0.0469 (5)0.0110 (5)0.0153 (5)0.0029 (4)
O10.173 (4)0.079 (2)0.084 (2)0.014 (2)0.039 (3)0.0038 (17)
N10.0503 (16)0.0491 (16)0.0521 (16)0.0006 (12)0.0104 (13)0.0017 (13)
N20.0472 (16)0.0521 (17)0.0603 (18)0.0057 (13)0.0065 (13)0.0016 (13)
N30.0501 (15)0.0472 (16)0.0474 (15)0.0029 (12)0.0070 (12)0.0100 (12)
N40.0535 (16)0.0387 (15)0.0467 (15)0.0051 (11)0.0117 (12)0.0005 (11)
N50.0487 (15)0.0426 (15)0.0472 (15)0.0031 (12)0.0089 (12)0.0017 (12)
C10.0482 (18)0.0409 (18)0.0530 (19)0.0035 (14)0.0094 (14)0.0003 (14)
C20.062 (2)0.058 (2)0.053 (2)0.0042 (16)0.0176 (18)0.0018 (16)
C30.050 (2)0.066 (2)0.070 (2)0.0055 (17)0.0200 (18)0.0079 (19)
C40.054 (2)0.0439 (19)0.062 (2)0.0058 (15)0.0085 (16)0.0106 (15)
C50.058 (2)0.071 (3)0.076 (3)0.0138 (18)0.0014 (19)0.001 (2)
C60.0440 (17)0.0379 (17)0.0480 (18)0.0021 (13)0.0074 (14)0.0000 (13)
C70.0524 (19)0.045 (2)0.0503 (19)0.0054 (14)0.0075 (15)0.0095 (15)
C80.0554 (19)0.0383 (18)0.062 (2)0.0087 (15)0.0090 (16)0.0038 (15)
C90.055 (2)0.0442 (19)0.0530 (19)0.0015 (14)0.0135 (15)0.0042 (14)
C100.075 (3)0.066 (3)0.051 (2)0.0156 (18)0.0149 (18)0.0060 (17)
C110.0273 (17)0.101 (3)0.059 (2)0.0081 (19)0.0141 (16)0.026 (2)
Geometric parameters (Å, º) top
Zn—N12.016 (3)C2—C31.341 (5)
Zn—N42.026 (2)C2—H20.9300
Zn—Cl22.2230 (9)C3—H30.9300
Zn—Cl12.2490 (10)C4—H4A0.9700
O1—C111.138 (5)C4—H4B0.9700
N1—C11.331 (4)C5—H5A0.9600
N1—C21.368 (4)C5—H5B0.9600
N2—C11.334 (4)C5—H5C0.9600
N2—C31.369 (4)C6—C91.493 (4)
N2—C51.454 (4)C7—C81.340 (4)
N3—C111.342 (5)C7—H70.9300
N3—C91.446 (4)C8—H80.9300
N3—C41.470 (4)C9—H9A0.9700
N4—C61.317 (4)C9—H9B0.9700
N4—C71.368 (4)C10—H10A0.9600
N5—C61.345 (4)C10—H10B0.9600
N5—C81.374 (4)C10—H10C0.9600
N5—C101.468 (4)C11—H110.9300
C1—C41.493 (4)
N1—Zn—N4108.44 (11)N3—C4—H4B109.2
N1—Zn—Cl2108.99 (8)C1—C4—H4B109.2
N4—Zn—Cl2104.89 (8)H4A—C4—H4B107.9
N1—Zn—Cl1106.03 (8)N2—C5—H5A109.5
N4—Zn—Cl1108.60 (8)N2—C5—H5B109.5
Cl2—Zn—Cl1119.53 (4)H5A—C5—H5B109.5
C1—N1—C2106.1 (3)N2—C5—H5C109.5
C1—N1—Zn129.1 (2)H5A—C5—H5C109.5
C2—N1—Zn124.8 (2)H5B—C5—H5C109.5
C1—N2—C3107.2 (3)N4—C6—N5110.7 (3)
C1—N2—C5127.2 (3)N4—C6—C9124.4 (3)
C3—N2—C5125.6 (3)N5—C6—C9124.9 (3)
C11—N3—C9111.8 (3)C8—C7—N4109.7 (3)
C11—N3—C4124.7 (3)C8—C7—H7125.2
C9—N3—C4123.4 (3)N4—C7—H7125.2
C6—N4—C7106.2 (3)C7—C8—N5106.4 (3)
C6—N4—Zn128.0 (2)C7—C8—H8126.8
C7—N4—Zn125.7 (2)N5—C8—H8126.8
C6—N5—C8107.0 (3)N3—C9—C6111.7 (2)
C6—N5—C10127.0 (3)N3—C9—H9A109.3
C8—N5—C10126.0 (3)C6—C9—H9A109.3
N1—C1—N2110.5 (3)N3—C9—H9B109.3
N1—C1—C4123.7 (3)C6—C9—H9B109.3
N2—C1—C4125.7 (3)H9A—C9—H9B107.9
C3—C2—N1109.1 (3)N5—C10—H10A109.5
C3—C2—H2125.4N5—C10—H10B109.5
N1—C2—H2125.4H10A—C10—H10B109.5
C2—C3—N2107.0 (3)N5—C10—H10C109.5
C2—C3—H3126.5H10A—C10—H10C109.5
N2—C3—H3126.5H10B—C10—H10C109.5
N3—C4—C1112.0 (3)O1—C11—N3111.6 (4)
N3—C4—H4A109.2O1—C11—H11124.2
C1—C4—H4A109.2N3—C11—H11124.2
N4—Zn—N1—C163.1 (3)C5—N2—C3—C2177.4 (3)
Cl2—Zn—N1—C1176.8 (3)C11—N3—C4—C172.1 (4)
Cl1—Zn—N1—C153.4 (3)C9—N3—C4—C1112.2 (3)
N4—Zn—N1—C2119.1 (3)N1—C1—C4—N366.0 (4)
Cl2—Zn—N1—C25.4 (3)N2—C1—C4—N3115.0 (4)
Cl1—Zn—N1—C2124.4 (2)C7—N4—C6—N50.6 (4)
N1—Zn—N4—C661.4 (3)Zn—N4—C6—N5176.5 (2)
Cl2—Zn—N4—C6177.7 (3)C7—N4—C6—C9177.8 (3)
Cl1—Zn—N4—C653.4 (3)Zn—N4—C6—C91.9 (5)
N1—Zn—N4—C7113.7 (3)C8—N5—C6—N40.8 (3)
Cl2—Zn—N4—C72.6 (3)C10—N5—C6—N4179.3 (3)
Cl1—Zn—N4—C7131.5 (2)C8—N5—C6—C9177.6 (3)
C2—N1—C1—N20.2 (4)C10—N5—C6—C92.4 (5)
Zn—N1—C1—N2178.4 (2)C6—N4—C7—C80.2 (4)
C2—N1—C1—C4178.9 (3)Zn—N4—C7—C8176.2 (2)
Zn—N1—C1—C40.8 (5)N4—C7—C8—N50.2 (4)
C3—N2—C1—N10.6 (4)C6—N5—C8—C70.6 (3)
C5—N2—C1—N1177.4 (3)C10—N5—C8—C7179.4 (3)
C3—N2—C1—C4178.6 (3)C11—N3—C9—C670.4 (3)
C5—N2—C1—C43.4 (5)C4—N3—C9—C6113.4 (3)
C1—N1—C2—C30.2 (4)N4—C6—C9—N369.1 (4)
Zn—N1—C2—C3178.1 (2)N5—C6—C9—N3109.1 (3)
N1—C2—C3—N20.5 (4)C9—N3—C11—O1175.2 (3)
C1—N2—C3—C20.7 (4)C4—N3—C11—O10.9 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O1i0.932.573.332 (5)140
Symmetry code: (i) x, y+1, z+1.
 

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