Diisoprop­yl(N,N,N',N'-tetra­methyl­ethylene­diamine)­zinc(II), the first crystal structure of a diisopropyl­zinc complex

Although diisopropyl­zinc has attracted considerable inter­est as a useful organometallic reagent over the past ten years, diisopropyl­zinc complexes are still absent in the present version of the Cambridge Structural Database. In the title compound, a tmeda (tmeda is N,N,N',N'-tetra­methyl­ethylene­diamine) adduct, [Zn(C₃H₇)₂(C₆H₁₆N₂)], the Zn^II atom, which lies on a crystallographic twofold rotation axis, is in a distorted tetra­hedral geometry. The mol­ecules are held together by dispersion forces, without any contacts within the sum of the van der Waals radii.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.024
• wR factor = 0.065
• Data-to-parameter ratio = 20.2

checkCIF/PLATON results

No syntax errors found



Alert level B
REFLT03_ALERT_3_B  Reflection count < 90% complete (theta max?)
           From the CIF: _diffrn_reflns_theta_max           26.99
           From the CIF: _diffrn_reflns_theta_full          25.00
           From the CIF: _reflns_number_total               1477
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         1656
           Completeness (_total/calc)             89.19%
PLAT022_ALERT_3_B Ratio Unique / Expected Reflections too Low ....       0.89
PLAT028_ALERT_3_B _diffrn_measured_fraction_theta_max  Low .......       0.89

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   3 ALERT level B = Potentially serious problem
   0 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   2 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
   3 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CrystalClear (Rigaku, 2000); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Diisopropyl(N,N,N',N'-tetramethylethylenediamine)zinc(II)

Crystal data

[Zn(C3H7)2(C6H16N2)]	F(000) = 584
Mr = 267.75	Dx = 1.175 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5464 reflections
a = 14.370 (4) Å	θ = 5.0–27.0°
b = 8.5935 (16) Å	µ = 1.60 mm^−1
c = 12.684 (3) Å	T = 293 K
β = 104.928 (8)°	Needle, colourless
V = 1513.4 (6) Å^3	0.2 × 0.08 × 0.08 mm
Z = 4

Data collection

Rigaku R-AXIS IIC image-plate system diffractometer	1477 independent reflections
Radiation source: rotating-anode X-ray tube, Rigaku RU-H3R	1407 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
Detector resolution: 105 pixels mm^-1	θmax = 27.0°, θmin = 5.0°
φ scans	h = −18→17
Absorption correction: multi-scan (CrystalClear; Rigaku, 2000)	k = −10→10
Tmin = 0.724, Tmax = 0.883	l = −16→15
5464 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.065	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0453P)^2 + 0.2577P] where P = (Fo^2 + 2Fc^2)/3
1477 reflections	(Δ/σ)max = 0.001
73 parameters	Δρmax = 0.71 e Å^−3
0 restraints	Δρmin = −0.52 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.11058 (11)	0.29879 (19)	0.43429 (13)	0.0226 (3)
H1A	0.1637	0.2299	0.4370	0.034*
H1B	0.1165	0.3431	0.5052	0.034*
H1C	0.1108	0.3804	0.3827	0.034*
C2	0.01558 (10)	0.20726 (16)	0.39899 (10)	0.0149 (3)
H2	0.0168	0.1242	0.4523	0.018*
C3	−0.06841 (11)	0.31554 (18)	0.39951 (12)	0.0210 (3)
H3A	−0.1272	0.2569	0.3835	0.031*
H3B	−0.0725	0.3950	0.3453	0.031*
H3C	−0.0583	0.3629	0.4701	0.031*
C4	−0.04513 (11)	−0.22989 (17)	0.27070 (13)	0.0202 (3)
H4A	−0.0815	−0.3242	0.2467	0.024*
H4B	−0.0269	−0.2294	0.3498	0.024*
C5	−0.15901 (12)	−0.11498 (17)	0.11480 (13)	0.0213 (3)
H5A	−0.1139	−0.1179	0.0706	0.032*
H5B	−0.2031	−0.0302	0.0918	0.032*
H5C	−0.1942	−0.2111	0.1069	0.032*
C6	−0.17632 (11)	−0.0722 (2)	0.29621 (13)	0.0217 (3)
H6A	−0.1425	−0.0552	0.3711	0.033*
H6B	−0.2155	−0.1638	0.2908	0.033*
H6C	−0.2165	0.0160	0.2696	0.033*
N1	−0.10647 (9)	−0.09313 (13)	0.23053 (10)	0.0151 (3)
Zn1	0.0000	0.10820 (2)	0.2500	0.01190 (11)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0196 (7)	0.0262 (8)	0.0209 (7)	−0.0057 (6)	0.0030 (6)	−0.0067 (6)
C2	0.0143 (6)	0.0211 (7)	0.0086 (6)	−0.0023 (5)	0.0020 (5)	−0.0007 (5)
C3	0.0217 (7)	0.0226 (7)	0.0189 (7)	0.0049 (6)	0.0055 (6)	−0.0002 (5)
C4	0.0211 (8)	0.0179 (7)	0.0206 (7)	−0.0021 (5)	0.0033 (6)	0.0026 (5)
C5	0.0182 (8)	0.0300 (8)	0.0129 (7)	−0.0074 (5)	−0.0007 (6)	−0.0021 (5)
C6	0.0160 (7)	0.0331 (8)	0.0171 (7)	−0.0052 (6)	0.0062 (6)	−0.0019 (6)
N1	0.0121 (6)	0.0208 (6)	0.0113 (6)	−0.0023 (4)	0.0010 (5)	−0.0001 (4)
Zn1	0.01033 (15)	0.01612 (15)	0.00858 (14)	0.000	0.00121 (9)	0.000

Geometric parameters (Å, º)

C1—C2	1.5387 (19)	C4—H4B	0.97
C1—H1A	0.96	C5—N1	1.4796 (19)
C1—H1B	0.96	C5—H5A	0.96
C1—H1C	0.96	C5—H5B	0.96
C2—C3	1.525 (2)	C5—H5C	0.96
C2—Zn1	2.0318 (14)	C6—N1	1.471 (2)
C2—H2	0.98	C6—H6A	0.96
C3—H3A	0.96	C6—H6B	0.96
C3—H3B	0.96	C6—H6C	0.96
C3—H3C	0.96	N1—Zn1	2.2804 (13)
C4—N1	1.4786 (19)	Zn1—C2^i	2.0318 (14)
C4—C4^i	1.519 (3)	Zn1—N1^i	2.2804 (13)
C4—H4A	0.97
C2—C1—H1A	109.5	N1—C5—H5A	109.5
C2—C1—H1B	109.5	N1—C5—H5B	109.5
H1A—C1—H1B	109.5	H5A—C5—H5B	109.5
C2—C1—H1C	109.5	N1—C5—H5C	109.5
H1A—C1—H1C	109.5	H5A—C5—H5C	109.5
H1B—C1—H1C	109.5	H5B—C5—H5C	109.5
C3—C2—C1	109.30 (12)	N1—C6—H6A	109.5
C3—C2—Zn1	111.22 (9)	N1—C6—H6B	109.5
C1—C2—Zn1	111.21 (9)	H6A—C6—H6B	109.5
C3—C2—H2	108.3	N1—C6—H6C	109.5
C1—C2—H2	108.3	H6A—C6—H6C	109.5
Zn1—C2—H2	108.3	H6B—C6—H6C	109.5
C2—C3—H3A	109.5	C6—N1—C4	109.58 (12)
C2—C3—H3B	109.5	C6—N1—C5	109.21 (12)
H3A—C3—H3B	109.5	C4—N1—C5	110.33 (12)
C2—C3—H3C	109.5	C6—N1—Zn1	112.49 (9)
H3A—C3—H3C	109.5	C4—N1—Zn1	104.00 (9)
H3B—C3—H3C	109.5	C5—N1—Zn1	111.12 (9)
N1—C4—C4^i	111.54 (11)	C2—Zn1—C2^i	130.46 (8)
N1—C4—H4A	109.3	C2—Zn1—N1	109.19 (5)
C4^i—C4—H4A	109.3	C2^i—Zn1—N1	107.88 (5)
N1—C4—H4B	109.3	C2—Zn1—N1^i	107.88 (5)
C4^i—C4—H4B	109.3	C2^i—Zn1—N1^i	109.19 (5)
H4A—C4—H4B	108.0	N1—Zn1—N1^i	81.31 (7)

Symmetry code: (i) −x, y, −z+1/2.