metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 70| Part 9| September 2014| Pages m320-m321

Crystal structure of di-μ-hydroxido-bis­{[N,N′-bis­­(2,6-di­methyl­phen­yl)pentane-2,4-diiminato(1–)]zinc}

aDepartment of Chemistry, University of Central Arkansas, 201 Donaghey Avenue, Conway, AR 72035, USA, and bDepartment of Chemistry and Biochemistry, University of Oklahoma, Norman, OK 73019, USA
*Correspondence e-mail: lyang@uca.edu

Edited by M. Weil, Vienna University of Technology, Austria (Received 14 July 2014; accepted 28 July 2014; online 6 August 2014)

The title compound, [Zn2(C21H25N2)2(OH)2], is a binuclear zinc complex formed by two bidentate β-diketiminate (nacnac) ligands and two μ-hydroxide O atoms, bridging two mononuclear units into a centrosymmetric dimeric unit. Each Zn2+ cation is coordinated by two N-donor atoms from the nacnac ligand and two O-donor atoms of hydroxide anions to give a distorted tetra­hedral coordination environment. The Zn—O bond lengths are 1.9643 (13) and 2.0022 (14) Å, and the two Zn—N bond lengths are 1.9696 (14) and 1.9823 (14) Å. The distance between the two Zn2+ cations in the dimer is 2.9420 (4) Å. Although hydroxide groups are present in the complex, no classical hydrogen-bonding inter­ations are observed because of the bulky β-diketiminate ligands.

1. Related literature

For similar compounds with a [Zn2(OH)2] diamond core structure supported by β-diketiminate ligands, see: Cheng et al. (2001[Cheng, M., Moore, D., Reczek, J. J., Chamberlain, B. M., Lobkovsky, E. B. & Coates, G. W. (2001). J. Am. Chem. Soc. 123, 8738-8749.]); Chisholm et al. (2002[Chisholm, M. H., Gallucci, J. & Phomphrai, K. (2002). Inorg. Chem. 41, 2785-2794.]); Gondzik et al. (2014[Gondzik, S., Schulz, S. & Wölper, C. (2014). Chem. Commun. 50, 1189-1191.]); Schulz et al. (2011[Schulz, S., Spielmann, J., Bläser, D. & Wölper, C. (2011). Chem. Commun. 47, 2676-2678.]). For the geometry index of four-coordinated metal cations, see: Yang et al. (2007[Yang, L., Wang, Z., Powell, D. R. & Houser, R. P. (2007). Dalton Trans. pp. 4439-4441.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • [Zn2(C21H25N2)2(OH)2]

  • Mr = 775.61

  • Monoclinic, P 21 /n

  • a = 12.8736 (4) Å

  • b = 8.7682 (3) Å

  • c = 17.4530 (5) Å

  • β = 105.222 (2)°

  • V = 1900.95 (10) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 1.30 mm−1

  • T = 100 K

  • 0.46 × 0.23 × 0.23 mm

2.2. Data collection

  • Bruker APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2007[Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.586, Tmax = 0.754

  • 22627 measured reflections

  • 3730 independent reflections

  • 3576 reflections with I > 2σ(I)

  • Rint = 0.016

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.029

  • wR(F2) = 0.079

  • S = 0.99

  • 3730 reflections

  • 230 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 1.06 e Å−3

  • Δρmin = −0.25 e Å−3

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXL2012 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information


Synthesis and crystallization top

The complex was synthesized from the reaction of water with the [Zn(Et)(N,N'-bis­(2,6-di­methyl­phenyl)­pentane-2,4-diiminato)] complex in Et2O. The solvent was removed under vacuum after the reaction, and a white powder was collected. Recrystallization of the white powder in saturated Et2O at 253 K led to the formation of colorless crystals.

Refinement top

The positions of hydrogen atoms bonded to carbon atoms were initially determined by geometrical considerations and refined by using a riding model. The hydrogen atom bonded to the oxygen atom was located in a difference map, and its position was refined independently. Hydrogen atom displacement parameters were set to 1.2Ueq (1.5 for methyl) of the respective parent atom.

Related literature top

For similar compounds with a [Zn2(OH)2] diamond core structure supported by β-diketimine ligands, see: Cheng et al. (2001); Chisholm et al. (2002); Gondzik et al. (2014); Schulz et al. (2011). For the geometry index of four-coordinated metal cations, see: Yang et al. (2007).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL2012 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title complex. Anisotropic displacement ellipsoids were drawn at the 30% probability level. Hydrogen atoms, except for the two oxygen donor atoms, have been omitted for clarity. [Symmetry code A: -x+2, -y+2, -z+2.]
Di-µ-hydroxido-bis{[N,N'-bis(2,6-dimethylphenyl)pentane-2,4-diiminato(1-)]zinc} top
Crystal data top
[Zn2(C21H25N2)2(OH)2]F(000) = 816
Mr = 775.61Dx = 1.355 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 12.8736 (4) ÅCell parameters from 7335 reflections
b = 8.7682 (3) Åθ = 2.3–28.3°
c = 17.4530 (5) ŵ = 1.30 mm1
β = 105.222 (2)°T = 100 K
V = 1900.95 (10) Å3Block, colorless
Z = 20.46 × 0.23 × 0.23 mm
Data collection top
Bruker APEX CCD
diffractometer
3576 reflections with I > 2σ(I)
ϕ and ω scansRint = 0.016
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
θmax = 26.0°, θmin = 1.8°
Tmin = 0.586, Tmax = 0.754h = 1515
22627 measured reflectionsk = 1010
3730 independent reflectionsl = 2121
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)] = 0.029Hydrogen site location: mixed
wR(F2) = 0.079H atoms treated by a mixture of independent and constrained refinement
S = 0.99 w = 1/[σ2(Fo2) + (0.050P)2 + 1.390P]
where P = (Fo2 + 2Fc2)/3
3730 reflections(Δ/σ)max = 0.002
230 parametersΔρmax = 1.06 e Å3
0 restraintsΔρmin = 0.25 e Å3
Crystal data top
[Zn2(C21H25N2)2(OH)2]V = 1900.95 (10) Å3
Mr = 775.61Z = 2
Monoclinic, P21/nMo Kα radiation
a = 12.8736 (4) ŵ = 1.30 mm1
b = 8.7682 (3) ÅT = 100 K
c = 17.4530 (5) Å0.46 × 0.23 × 0.23 mm
β = 105.222 (2)°
Data collection top
Bruker APEX CCD
diffractometer
3730 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
3576 reflections with I > 2σ(I)
Tmin = 0.586, Tmax = 0.754Rint = 0.016
22627 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0290 restraints
wR(F2) = 0.079H atoms treated by a mixture of independent and constrained refinement
S = 0.99Δρmax = 1.06 e Å3
3730 reflectionsΔρmin = 0.25 e Å3
230 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Zn10.95859 (2)0.92266 (2)0.92324 (2)0.02197 (9)
N11.01789 (11)0.88907 (16)0.83143 (8)0.0201 (3)
N20.81321 (11)0.83790 (17)0.87559 (8)0.0228 (3)
O10.96361 (10)1.13369 (16)0.96789 (7)0.0259 (3)
H10.9667 (18)1.209 (3)0.9400 (15)0.038 (7)*
C30.95099 (13)0.87215 (19)0.75919 (10)0.0210 (3)
C40.83960 (13)0.8525 (2)0.74383 (10)0.0223 (3)
H40.80070.85930.68960.027*
C50.77700 (13)0.8241 (2)0.79754 (10)0.0225 (3)
C60.99662 (14)0.8736 (2)0.68752 (10)0.0262 (4)
H6A1.04050.96540.68890.039*
H6B0.93750.87350.63890.039*
H6C1.04140.78290.68840.039*
C70.66271 (13)0.7706 (2)0.76132 (10)0.0267 (4)
H7A0.65370.66740.78020.040*
H7B0.64830.76980.70330.040*
H7C0.61230.83990.77700.040*
C80.74730 (13)0.7795 (2)0.92370 (10)0.0241 (4)
C90.76109 (14)0.6264 (2)0.94808 (10)0.0259 (4)
C100.69362 (16)0.5658 (2)0.99114 (11)0.0305 (4)
H100.70110.46211.00740.037*
C110.61560 (15)0.6562 (3)1.01037 (11)0.0335 (4)
H110.56840.61351.03830.040*
C120.60651 (14)0.8085 (3)0.98893 (11)0.0333 (4)
H120.55410.86981.00370.040*
C130.67270 (14)0.8742 (2)0.94604 (11)0.0294 (4)
C140.84837 (15)0.5304 (2)0.92859 (12)0.0309 (4)
H14A0.84180.42480.94510.046*
H14B0.91910.57070.95680.046*
H14C0.84080.53340.87120.046*
C150.66482 (18)1.0416 (3)0.92477 (14)0.0394 (5)
H15A0.73651.08800.94130.059*
H15B0.61681.09250.95200.059*
H15C0.63601.05300.86720.059*
C161.13079 (13)0.8705 (2)0.83836 (9)0.0205 (3)
C171.17176 (14)0.7214 (2)0.84038 (10)0.0238 (3)
C181.28096 (14)0.7028 (2)0.84487 (11)0.0281 (4)
H181.31010.60300.84630.034*
C191.34732 (14)0.8281 (2)0.84731 (11)0.0290 (4)
H191.42120.81400.84940.035*
C201.30597 (14)0.9738 (2)0.84663 (10)0.0277 (4)
H201.35221.05910.84880.033*
C211.19747 (14)0.9978 (2)0.84288 (10)0.0228 (3)
C221.09984 (17)0.5850 (2)0.83697 (13)0.0314 (4)
H22A1.06520.59020.88060.047*
H22B1.14290.49160.84190.047*
H22C1.04460.58430.78620.047*
C231.15467 (15)1.1575 (2)0.84357 (11)0.0285 (4)
H23A1.08521.16610.80380.043*
H23B1.20581.23010.83110.043*
H23C1.14521.18030.89630.043*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.01621 (12)0.03297 (14)0.01712 (12)0.00048 (7)0.00511 (8)0.00413 (7)
N10.0170 (7)0.0258 (7)0.0179 (7)0.0004 (5)0.0054 (5)0.0020 (5)
N20.0172 (6)0.0314 (8)0.0201 (7)0.0002 (6)0.0056 (5)0.0005 (6)
O10.0264 (6)0.0323 (7)0.0186 (6)0.0012 (5)0.0052 (5)0.0017 (5)
C30.0231 (8)0.0214 (8)0.0196 (8)0.0010 (6)0.0074 (6)0.0003 (6)
C40.0212 (8)0.0272 (9)0.0179 (8)0.0000 (6)0.0039 (6)0.0015 (6)
C50.0190 (8)0.0248 (8)0.0226 (8)0.0014 (6)0.0037 (6)0.0023 (7)
C60.0239 (8)0.0366 (10)0.0191 (8)0.0015 (7)0.0073 (7)0.0002 (7)
C70.0204 (8)0.0353 (10)0.0227 (8)0.0037 (7)0.0028 (7)0.0038 (7)
C80.0164 (7)0.0375 (10)0.0177 (8)0.0011 (7)0.0033 (6)0.0005 (7)
C90.0215 (8)0.0347 (9)0.0201 (8)0.0020 (7)0.0029 (7)0.0022 (7)
C100.0296 (10)0.0388 (11)0.0216 (9)0.0083 (8)0.0040 (7)0.0017 (7)
C110.0255 (9)0.0542 (13)0.0217 (9)0.0101 (9)0.0081 (7)0.0004 (8)
C120.0205 (8)0.0561 (13)0.0243 (9)0.0028 (8)0.0078 (7)0.0023 (8)
C130.0208 (8)0.0431 (11)0.0242 (9)0.0042 (8)0.0057 (7)0.0024 (8)
C140.0295 (9)0.0311 (10)0.0318 (10)0.0015 (8)0.0077 (8)0.0006 (8)
C150.0364 (11)0.0441 (12)0.0418 (12)0.0127 (9)0.0177 (9)0.0040 (10)
C160.0187 (8)0.0280 (9)0.0157 (7)0.0011 (6)0.0062 (6)0.0011 (6)
C170.0251 (8)0.0276 (9)0.0204 (8)0.0023 (7)0.0087 (6)0.0009 (7)
C180.0274 (9)0.0340 (10)0.0248 (9)0.0089 (7)0.0102 (7)0.0017 (7)
C190.0185 (8)0.0461 (11)0.0235 (9)0.0032 (7)0.0071 (7)0.0007 (8)
C200.0220 (8)0.0392 (10)0.0226 (9)0.0064 (7)0.0072 (7)0.0025 (8)
C210.0243 (8)0.0281 (9)0.0167 (8)0.0002 (7)0.0066 (6)0.0006 (6)
C220.0341 (10)0.0249 (9)0.0386 (11)0.0014 (7)0.0154 (9)0.0015 (7)
C230.0315 (9)0.0258 (9)0.0296 (9)0.0016 (7)0.0104 (7)0.0007 (7)
Geometric parameters (Å, º) top
Zn1—O1i1.9643 (13)C11—H110.9500
Zn1—N11.9696 (14)C12—C131.397 (3)
Zn1—N21.9823 (14)C12—H120.9500
Zn1—O12.0022 (14)C13—C151.511 (3)
N1—C31.335 (2)C14—H14A0.9800
N1—C161.436 (2)C14—H14B0.9800
N2—C51.324 (2)C14—H14C0.9800
N2—C81.436 (2)C15—H15A0.9800
O1—H10.83 (3)C15—H15B0.9800
C3—C41.398 (2)C15—H15C0.9800
C3—C61.515 (2)C16—C211.398 (2)
C4—C51.410 (2)C16—C171.407 (2)
C4—H40.9500C17—C181.397 (2)
C5—C71.515 (2)C17—C221.504 (3)
C6—H6A0.9800C18—C191.386 (3)
C6—H6B0.9800C18—H180.9500
C6—H6C0.9800C19—C201.383 (3)
C7—H7A0.9800C19—H190.9500
C7—H7B0.9800C20—C211.397 (2)
C7—H7C0.9800C20—H200.9500
C8—C131.400 (3)C21—C231.506 (3)
C8—C91.406 (3)C22—H22A0.9800
C9—C101.394 (3)C22—H22B0.9800
C9—C141.512 (3)C22—H22C0.9800
C10—C111.388 (3)C23—H23A0.9800
C10—H100.9500C23—H23B0.9800
C11—C121.383 (3)C23—H23C0.9800
O1i—Zn1—N1122.77 (6)C11—C12—C13121.50 (18)
O1i—Zn1—N2119.80 (6)C11—C12—H12119.2
N1—Zn1—N297.33 (6)C13—C12—H12119.2
O1i—Zn1—O184.25 (6)C12—C13—C8117.67 (19)
N1—Zn1—O1118.36 (6)C12—C13—C15121.39 (18)
N2—Zn1—O1116.11 (6)C8—C13—C15120.94 (17)
C3—N1—C16117.04 (14)C9—C14—H14A109.5
C3—N1—Zn1119.54 (11)C9—C14—H14B109.5
C16—N1—Zn1123.26 (11)H14A—C14—H14B109.5
C5—N2—C8117.81 (14)C9—C14—H14C109.5
C5—N2—Zn1120.29 (11)H14A—C14—H14C109.5
C8—N2—Zn1121.74 (11)H14B—C14—H14C109.5
Zn1i—O1—Zn195.75 (6)C13—C15—H15A109.5
Zn1i—O1—H1132.7 (17)C13—C15—H15B109.5
Zn1—O1—H1120.8 (17)H15A—C15—H15B109.5
N1—C3—C4124.70 (15)C13—C15—H15C109.5
N1—C3—C6118.99 (15)H15A—C15—H15C109.5
C4—C3—C6116.30 (15)H15B—C15—H15C109.5
C3—C4—C5129.11 (15)C21—C16—C17121.33 (15)
C3—C4—H4115.4C21—C16—N1120.49 (15)
C5—C4—H4115.4C17—C16—N1118.17 (15)
N2—C5—C4124.02 (15)C18—C17—C16118.38 (16)
N2—C5—C7119.89 (15)C18—C17—C22120.61 (17)
C4—C5—C7116.07 (15)C16—C17—C22121.01 (15)
C3—C6—H6A109.5C19—C18—C17120.81 (17)
C3—C6—H6B109.5C19—C18—H18119.6
H6A—C6—H6B109.5C17—C18—H18119.6
C3—C6—H6C109.5C20—C19—C18119.98 (16)
H6A—C6—H6C109.5C20—C19—H19120.0
H6B—C6—H6C109.5C18—C19—H19120.0
C5—C7—H7A109.5C19—C20—C21121.15 (18)
C5—C7—H7B109.5C19—C20—H20119.4
H7A—C7—H7B109.5C21—C20—H20119.4
C5—C7—H7C109.5C20—C21—C16118.32 (17)
H7A—C7—H7C109.5C20—C21—C23120.18 (17)
H7B—C7—H7C109.5C16—C21—C23121.50 (16)
C13—C8—C9121.56 (16)C17—C22—H22A109.5
C13—C8—N2120.37 (17)C17—C22—H22B109.5
C9—C8—N2118.06 (15)H22A—C22—H22B109.5
C10—C9—C8118.67 (17)C17—C22—H22C109.5
C10—C9—C14120.93 (18)H22A—C22—H22C109.5
C8—C9—C14120.39 (16)H22B—C22—H22C109.5
C11—C10—C9120.38 (19)C21—C23—H23A109.5
C11—C10—H10119.8C21—C23—H23B109.5
C9—C10—H10119.8H23A—C23—H23B109.5
C12—C11—C10120.06 (17)C21—C23—H23C109.5
C12—C11—H11120.0H23A—C23—H23C109.5
C10—C11—H11120.0H23B—C23—H23C109.5
C16—N1—C3—C4165.14 (16)C11—C12—C13—C81.5 (3)
Zn1—N1—C3—C410.5 (2)C11—C12—C13—C15178.18 (19)
C16—N1—C3—C614.8 (2)C9—C8—C13—C124.5 (3)
Zn1—N1—C3—C6169.60 (12)N2—C8—C13—C12176.31 (16)
N1—C3—C4—C510.3 (3)C9—C8—C13—C15175.20 (17)
C6—C3—C4—C5169.62 (18)N2—C8—C13—C154.0 (3)
C8—N2—C5—C4169.09 (16)C3—N1—C16—C21100.95 (19)
Zn1—N2—C5—C46.4 (2)Zn1—N1—C16—C2183.61 (18)
C8—N2—C5—C79.1 (2)C3—N1—C16—C1779.0 (2)
Zn1—N2—C5—C7175.34 (12)Zn1—N1—C16—C1796.43 (16)
C3—C4—C5—N212.6 (3)C21—C16—C17—C181.7 (2)
C3—C4—C5—C7165.64 (18)N1—C16—C17—C18178.23 (15)
C5—N2—C8—C1391.7 (2)C21—C16—C17—C22178.88 (17)
Zn1—N2—C8—C1392.82 (17)N1—C16—C17—C221.2 (2)
C5—N2—C8—C989.03 (19)C16—C17—C18—C190.0 (3)
Zn1—N2—C8—C986.44 (18)C22—C17—C18—C19179.42 (17)
C13—C8—C9—C104.2 (3)C17—C18—C19—C201.1 (3)
N2—C8—C9—C10176.53 (15)C18—C19—C20—C210.5 (3)
C13—C8—C9—C14175.09 (16)C19—C20—C21—C161.1 (3)
N2—C8—C9—C144.2 (2)C19—C20—C21—C23179.00 (16)
C8—C9—C10—C110.9 (3)C17—C16—C21—C202.3 (2)
C14—C9—C10—C11178.37 (17)N1—C16—C21—C20177.69 (15)
C9—C10—C11—C122.0 (3)C17—C16—C21—C23177.87 (16)
C10—C11—C12—C131.7 (3)N1—C16—C21—C232.2 (2)
Symmetry code: (i) x+2, y+2, z+2.

Experimental details

Crystal data
Chemical formula[Zn2(C21H25N2)2(OH)2]
Mr775.61
Crystal system, space groupMonoclinic, P21/n
Temperature (K)100
a, b, c (Å)12.8736 (4), 8.7682 (3), 17.4530 (5)
β (°) 105.222 (2)
V3)1900.95 (10)
Z2
Radiation typeMo Kα
µ (mm1)1.30
Crystal size (mm)0.46 × 0.23 × 0.23
Data collection
DiffractometerBruker APEX CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2007)
Tmin, Tmax0.586, 0.754
No. of measured, independent and
observed [I > 2σ(I)] reflections
22627, 3730, 3576
Rint0.016
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.029, 0.079, 0.99
No. of reflections3730
No. of parameters230
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)1.06, 0.25

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008), SHELXL2012 (Sheldrick, 2008).

 

Acknowledgements

The authors thank the National Science Foundation (grant No. CHE-0130835) and the University of Oklahoma for funds to purchase of the X-ray instrument and computers.

References

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Volume 70| Part 9| September 2014| Pages m320-m321
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