Bis[methyl 3-(propyl-amino)-but-2-eno-ato]zinc.

The title compound, [Zn(C(8)H(14)NO(2))(2)], represents a zinc complex with the Zn(2+) cation coordinated by two O and two N atoms in a distorted tetrahedral geometry.

Related literature

For background to ZnO and its applications, see: Norton et al. (2004 ▶); Groenen et al. (2005 ▶); Wan et al. (2004 ▶). For the growth of ZnO, see: Tribolate et al. (1999 ▶); Fan et al. (2005 ▶); El Hichou et al. (2004 ▶); Hoon et al. (2011 ▶); Jong et al. (2009 ▶); Malandrino et al. (2005 ▶). For ZnO precursors, see: Smith (1983 ▶); Sato et al. (1994 ▶). The corresponding complex is a monomer; its structure consists of a Zn2+ cation with a distorted tetrahedral coordin­ation (Matthews et al., 2006 ▶).

Experimental

Crystal data

[Zn(C8H14NO2)2]

M = 377.77

Triclinic,

a = 7.8087 (5) Å

b = 9.4353 (6) Å

c = 12.8788 (11) Å

α = 76.820 (3)°

β = 77.381 (3)°

γ = 83.413 (3)°

V = 899.46 (11) Å3

Z = 2

Mo Kα radiation

μ = 1.39 mm−1

T = 103 K

0.64 × 0.51 × 0.13 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T min = 0.471, T max = 0.840

9957 measured reflections

4977 independent reflections

4508 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.070

S = 1.00

4977 reflections

214 parameters

H-atom parameters constrained

Δρmax = 0.82 e Å−3

Δρmin = −0.54 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681104520X/bt5685sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681104520X/bt5685Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Zn(C8H14NO2)2]	Z = 2
Mr = 377.77	F(000) = 400
Triclinic, P1	Dx = 1.395 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8087 (5) Å	Cell parameters from 7001 reflections
b = 9.4353 (6) Å	θ = 2.3–24.6°
c = 12.8788 (11) Å	µ = 1.39 mm−1
α = 76.820 (3)°	T = 103 K
β = 77.381 (3)°	Plate, colourless
γ = 83.413 (3)°	0.64 × 0.51 × 0.13 mm
V = 899.46 (11) Å3

Bruker SMART CCD area-detector diffractometer	4977 independent reflections
Radiation source: fine-focus sealed tube	4508 reflections with I > 2σ(I)
graphite	Rint = 0.020
phi and ω scans	θmax = 30.7°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −9→11
Tmin = 0.471, Tmax = 0.840	k = −12→12
9957 measured reflections	l = −17→18

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.070	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0336P)2 + 0.4769P] where P = (Fo2 + 2Fc2)/3
4977 reflections	(Δ/σ)max = 0.003
214 parameters	Δρmax = 0.82 e Å−3
0 restraints	Δρmin = −0.54 e Å−3

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.

	x	y	z	Uiso*/Ueq
Zn	0.54308 (2)	0.924864 (17)	0.751108 (12)	0.01951 (5)
O1A	0.32476 (13)	0.81656 (11)	0.79509 (8)	0.0236 (2)
O2A	0.15956 (15)	0.64045 (12)	0.90620 (9)	0.0302 (2)
O1B	0.46956 (13)	1.13117 (11)	0.69599 (8)	0.02141 (19)
O2B	0.47457 (14)	1.33455 (11)	0.56379 (8)	0.0244 (2)
N1A	0.61225 (15)	0.87359 (13)	0.89469 (9)	0.0202 (2)
N1B	0.69909 (15)	0.88855 (13)	0.61512 (9)	0.0199 (2)
C1A	0.0663 (2)	0.65066 (19)	0.82025 (14)	0.0326 (3)
H1AA	−0.0258	0.5813	0.8439	0.049*
H1AB	0.1483	0.6278	0.7560	0.049*
H1AC	0.0127	0.7499	0.8021	0.049*
C2A	0.30075 (18)	0.72305 (15)	0.88369 (11)	0.0225 (3)
C3A	0.3992 (2)	0.69008 (16)	0.96517 (11)	0.0246 (3)
H3AA	0.3658	0.6099	1.0233	0.030*
C4A	0.54370 (19)	0.76365 (15)	0.97014 (11)	0.0212 (3)
C5A	0.6216 (2)	0.70783 (17)	1.07104 (12)	0.0276 (3)
H5AA	0.7470	0.6799	1.0496	0.041*
H5AB	0.5609	0.6227	1.1160	0.041*
H5AC	0.6073	0.7848	1.1127	0.041*
C6A	0.75495 (18)	0.94490 (15)	0.91732 (11)	0.0217 (3)
H6AA	0.8526	0.8712	0.9317	0.026*
H6AB	0.7105	0.9852	0.9835	0.026*
C7A	0.8239 (2)	1.06658 (16)	0.82344 (12)	0.0252 (3)
H7AA	0.7286	1.1437	0.8120	0.030*
H7AB	0.8621	1.0279	0.7561	0.030*
C8A	0.9787 (2)	1.13208 (18)	0.84601 (13)	0.0303 (3)
H8AA	1.0179	1.2130	0.7856	0.045*
H8AB	1.0756	1.0571	0.8533	0.045*
H8AC	0.9417	1.1682	0.9136	0.045*
C1B	0.3431 (2)	1.40060 (16)	0.63758 (12)	0.0254 (3)
H1BA	0.3152	1.5019	0.6030	0.038*
H1BB	0.3871	1.3986	0.7036	0.038*
H1BC	0.2367	1.3466	0.6567	0.038*
C2B	0.53266 (17)	1.19383 (15)	0.59936 (11)	0.0198 (2)
C3B	0.65608 (19)	1.13903 (16)	0.52004 (11)	0.0227 (3)
H3BA	0.6949	1.2061	0.4539	0.027*
C4B	0.72970 (17)	0.99394 (15)	0.52762 (11)	0.0203 (2)
C5B	0.8511 (2)	0.96427 (17)	0.42470 (11)	0.0251 (3)
H5BA	0.9607	0.9128	0.4425	0.038*
H5BB	0.8773	1.0569	0.3735	0.038*
H5BC	0.7938	0.9039	0.3915	0.038*
C6B	0.78253 (19)	0.74229 (15)	0.60851 (12)	0.0239 (3)
H6BA	0.9067	0.7392	0.6156	0.029*
H6BB	0.7819	0.7233	0.5361	0.029*
C7B	0.6909 (2)	0.62329 (16)	0.69560 (13)	0.0276 (3)
H7BA	0.5660	0.6270	0.6899	0.033*
H7BB	0.6946	0.6397	0.7683	0.033*
C8B	0.7791 (2)	0.47334 (17)	0.68364 (15)	0.0345 (3)
H8BA	0.7201	0.3983	0.7421	0.052*
H8BB	0.9032	0.4702	0.6881	0.052*
H8BC	0.7706	0.4552	0.6130	0.052*

	U11	U22	U33	U12	U13	U23
Zn	0.01943 (8)	0.02190 (8)	0.01611 (8)	−0.00083 (6)	−0.00332 (5)	−0.00224 (5)
O1A	0.0198 (5)	0.0271 (5)	0.0231 (5)	−0.0020 (4)	−0.0047 (4)	−0.0026 (4)
O2A	0.0254 (5)	0.0325 (6)	0.0328 (6)	−0.0100 (4)	−0.0064 (4)	−0.0023 (4)
O1B	0.0212 (5)	0.0235 (5)	0.0181 (4)	−0.0015 (4)	−0.0029 (4)	−0.0023 (4)
O2B	0.0245 (5)	0.0230 (5)	0.0217 (5)	0.0005 (4)	−0.0015 (4)	−0.0003 (4)
N1A	0.0203 (5)	0.0225 (5)	0.0181 (5)	−0.0012 (4)	−0.0037 (4)	−0.0048 (4)
N1B	0.0175 (5)	0.0237 (5)	0.0195 (5)	−0.0019 (4)	−0.0048 (4)	−0.0055 (4)
C1A	0.0245 (7)	0.0379 (8)	0.0389 (8)	−0.0046 (6)	−0.0085 (6)	−0.0120 (7)
C2A	0.0197 (6)	0.0222 (6)	0.0244 (6)	−0.0017 (5)	−0.0011 (5)	−0.0054 (5)
C3A	0.0273 (7)	0.0235 (6)	0.0212 (6)	−0.0043 (5)	−0.0034 (5)	−0.0013 (5)
C4A	0.0224 (6)	0.0223 (6)	0.0181 (6)	0.0019 (5)	−0.0033 (5)	−0.0048 (5)
C5A	0.0337 (8)	0.0294 (7)	0.0189 (6)	−0.0040 (6)	−0.0074 (5)	−0.0003 (5)
C6A	0.0203 (6)	0.0258 (6)	0.0196 (6)	−0.0016 (5)	−0.0046 (5)	−0.0055 (5)
C7A	0.0219 (7)	0.0296 (7)	0.0233 (6)	−0.0043 (5)	−0.0044 (5)	−0.0028 (5)
C8A	0.0225 (7)	0.0362 (8)	0.0323 (7)	−0.0074 (6)	−0.0047 (6)	−0.0054 (6)
C1B	0.0256 (7)	0.0230 (6)	0.0244 (6)	0.0011 (5)	−0.0022 (5)	−0.0026 (5)
C2B	0.0163 (6)	0.0224 (6)	0.0209 (6)	−0.0030 (5)	−0.0062 (5)	−0.0019 (5)
C3B	0.0205 (6)	0.0254 (6)	0.0196 (6)	−0.0036 (5)	−0.0019 (5)	−0.0005 (5)
C4B	0.0152 (6)	0.0285 (6)	0.0188 (6)	−0.0034 (5)	−0.0047 (4)	−0.0062 (5)
C5B	0.0227 (7)	0.0326 (7)	0.0196 (6)	−0.0028 (5)	−0.0016 (5)	−0.0065 (5)
C6B	0.0235 (7)	0.0249 (6)	0.0237 (6)	0.0002 (5)	−0.0038 (5)	−0.0076 (5)
C7B	0.0242 (7)	0.0234 (7)	0.0331 (7)	−0.0011 (5)	−0.0028 (6)	−0.0048 (6)
C8B	0.0321 (8)	0.0245 (7)	0.0447 (9)	0.0001 (6)	−0.0043 (7)	−0.0070 (6)

Zn—O1B	1.9784 (10)	C6A—H6AB	0.9900
Zn—N1A	1.9784 (12)	C7A—C8A	1.527 (2)
Zn—N1B	1.9785 (11)	C7A—H7AA	0.9900
Zn—O1A	1.9963 (10)	C7A—H7AB	0.9900
O1A—C2A	1.2653 (17)	C8A—H8AA	0.9800
O2A—C2A	1.3644 (17)	C8A—H8AB	0.9800
O2A—C1A	1.432 (2)	C8A—H8AC	0.9800
O1B—C2B	1.2666 (16)	C1B—H1BA	0.9800
O2B—C2B	1.3615 (16)	C1B—H1BB	0.9800
O2B—C1B	1.4292 (17)	C1B—H1BC	0.9800
N1A—C4A	1.3218 (18)	C2B—C3B	1.3915 (19)
N1A—C6A	1.4773 (18)	C3B—C4B	1.413 (2)
N1B—C4B	1.3197 (18)	C3B—H3BA	0.9500
N1B—C6B	1.4694 (18)	C4B—C5B	1.5143 (19)
C1A—H1AA	0.9800	C5B—H5BA	0.9800
C1A—H1AB	0.9800	C5B—H5BB	0.9800
C1A—H1AC	0.9800	C5B—H5BC	0.9800
C2A—C3A	1.392 (2)	C6B—C7B	1.513 (2)
C3A—C4A	1.411 (2)	C6B—H6BA	0.9900
C3A—H3AA	0.9500	C6B—H6BB	0.9900
C4A—C5A	1.515 (2)	C7B—C8B	1.526 (2)
C5A—H5AA	0.9800	C7B—H7BA	0.9900
C5A—H5AB	0.9800	C7B—H7BB	0.9900
C5A—H5AC	0.9800	C8B—H8BA	0.9800
C6A—C7A	1.515 (2)	C8B—H8BB	0.9800
C6A—H6AA	0.9900	C8B—H8BC	0.9800
O1B—Zn—N1A	117.85 (4)	C8A—C7A—H7AB	109.5
O1B—Zn—N1B	97.63 (4)	H7AA—C7A—H7AB	108.0
N1A—Zn—N1B	123.66 (5)	C7A—C8A—H8AA	109.5
O1B—Zn—O1A	106.41 (4)	C7A—C8A—H8AB	109.5
N1A—Zn—O1A	96.73 (5)	H8AA—C8A—H8AB	109.5
N1B—Zn—O1A	114.34 (5)	C7A—C8A—H8AC	109.5
C2A—O1A—Zn	119.24 (9)	H8AA—C8A—H8AC	109.5
C2A—O2A—C1A	116.87 (12)	H8AB—C8A—H8AC	109.5
C2B—O1B—Zn	120.03 (9)	O2B—C1B—H1BA	109.5
C2B—O2B—C1B	117.56 (11)	O2B—C1B—H1BB	109.5
C4A—N1A—C6A	117.53 (12)	H1BA—C1B—H1BB	109.5
C4A—N1A—Zn	120.54 (10)	O2B—C1B—H1BC	109.5
C6A—N1A—Zn	121.60 (9)	H1BA—C1B—H1BC	109.5
C4B—N1B—C6B	118.11 (11)	H1BB—C1B—H1BC	109.5
C4B—N1B—Zn	121.21 (9)	O1B—C2B—O2B	118.07 (12)
C6B—N1B—Zn	120.67 (9)	O1B—C2B—C3B	129.19 (13)
O2A—C1A—H1AA	109.5	O2B—C2B—C3B	112.75 (12)
O2A—C1A—H1AB	109.5	C2B—C3B—C4B	126.74 (13)
H1AA—C1A—H1AB	109.5	C2B—C3B—H3BA	116.6
O2A—C1A—H1AC	109.5	C4B—C3B—H3BA	116.6
H1AA—C1A—H1AC	109.5	N1B—C4B—C3B	124.95 (12)
H1AB—C1A—H1AC	109.5	N1B—C4B—C5B	120.39 (12)
O1A—C2A—O2A	117.82 (13)	C3B—C4B—C5B	114.65 (12)
O1A—C2A—C3A	129.20 (13)	C4B—C5B—H5BA	109.5
O2A—C2A—C3A	112.99 (12)	C4B—C5B—H5BB	109.5
C2A—C3A—C4A	126.59 (13)	H5BA—C5B—H5BB	109.5
C2A—C3A—H3AA	116.7	C4B—C5B—H5BC	109.5
C4A—C3A—H3AA	116.7	H5BA—C5B—H5BC	109.5
N1A—C4A—C3A	124.94 (13)	H5BB—C5B—H5BC	109.5
N1A—C4A—C5A	119.84 (13)	N1B—C6B—C7B	112.72 (11)
C3A—C4A—C5A	115.22 (12)	N1B—C6B—H6BA	109.0
C4A—C5A—H5AA	109.5	C7B—C6B—H6BA	109.0
C4A—C5A—H5AB	109.5	N1B—C6B—H6BB	109.0
H5AA—C5A—H5AB	109.5	C7B—C6B—H6BB	109.0
C4A—C5A—H5AC	109.5	H6BA—C6B—H6BB	107.8
H5AA—C5A—H5AC	109.5	C6B—C7B—C8B	110.83 (13)
H5AB—C5A—H5AC	109.5	C6B—C7B—H7BA	109.5
N1A—C6A—C7A	112.03 (11)	C8B—C7B—H7BA	109.5
N1A—C6A—H6AA	109.2	C6B—C7B—H7BB	109.5
C7A—C6A—H6AA	109.2	C8B—C7B—H7BB	109.5
N1A—C6A—H6AB	109.2	H7BA—C7B—H7BB	108.1
C7A—C6A—H6AB	109.2	C7B—C8B—H8BA	109.5
H6AA—C6A—H6AB	107.9	C7B—C8B—H8BB	109.5
C6A—C7A—C8A	110.95 (12)	H8BA—C8B—H8BB	109.5
C6A—C7A—H7AA	109.5	C7B—C8B—H8BC	109.5
C8A—C7A—H7AA	109.5	H8BA—C8B—H8BC	109.5
C6A—C7A—H7AB	109.5	H8BB—C8B—H8BC	109.5
O1B—Zn—O1A—C2A	−136.62 (10)	C6A—N1A—C4A—C3A	175.45 (13)
N1A—Zn—O1A—C2A	−14.94 (11)	Zn—N1A—C4A—C3A	−11.12 (19)
N1B—Zn—O1A—C2A	116.82 (10)	C6A—N1A—C4A—C5A	−4.78 (18)
N1A—Zn—O1B—C2B	132.15 (10)	Zn—N1A—C4A—C5A	168.66 (10)
N1B—Zn—O1B—C2B	−2.54 (11)	C2A—C3A—C4A—N1A	−2.6 (2)
O1A—Zn—O1B—C2B	−120.76 (10)	C2A—C3A—C4A—C5A	177.56 (14)
O1B—Zn—N1A—C4A	129.69 (10)	C4A—N1A—C6A—C7A	178.77 (12)
N1B—Zn—N1A—C4A	−108.15 (11)	Zn—N1A—C6A—C7A	5.41 (15)
O1A—Zn—N1A—C4A	17.10 (11)	N1A—C6A—C7A—C8A	−176.50 (12)
O1B—Zn—N1A—C6A	−57.14 (11)	Zn—O1B—C2B—O2B	178.12 (9)
N1B—Zn—N1A—C6A	65.01 (11)	Zn—O1B—C2B—C3B	−1.2 (2)
O1A—Zn—N1A—C6A	−169.74 (10)	C1B—O2B—C2B—O1B	−1.40 (18)
O1B—Zn—N1B—C4B	3.50 (11)	C1B—O2B—C2B—C3B	178.06 (12)
N1A—Zn—N1B—C4B	−127.45 (10)	O1B—C2B—C3B—C4B	5.5 (3)
O1A—Zn—N1B—C4B	115.43 (10)	O2B—C2B—C3B—C4B	−173.93 (13)
O1B—Zn—N1B—C6B	−175.72 (10)	C6B—N1B—C4B—C3B	178.33 (13)
N1A—Zn—N1B—C6B	53.32 (12)	Zn—N1B—C4B—C3B	−0.91 (19)
O1A—Zn—N1B—C6B	−63.79 (11)	C6B—N1B—C4B—C5B	−1.41 (19)
Zn—O1A—C2A—O2A	−173.49 (9)	Zn—N1B—C4B—C5B	179.35 (10)
Zn—O1A—C2A—C3A	6.7 (2)	C2B—C3B—C4B—N1B	−4.1 (2)
C1A—O2A—C2A—O1A	9.44 (19)	C2B—C3B—C4B—C5B	175.68 (14)
C1A—O2A—C2A—C3A	−170.72 (13)	C4B—N1B—C6B—C7B	−159.60 (13)
O1A—C2A—C3A—C4A	5.2 (3)	Zn—N1B—C6B—C7B	19.65 (16)
O2A—C2A—C3A—C4A	−174.58 (13)	N1B—C6B—C7B—C8B	178.50 (13)

Zn—O1B	1.9784 (10)
Zn—N1A	1.9784 (12)
Zn—N1B	1.9785 (11)
Zn—O1A	1.9963 (10)

O1B—Zn—N1A	117.85 (4)
O1B—Zn—N1B	97.63 (4)
N1A—Zn—N1B	123.66 (5)
O1B—Zn—O1A	106.41 (4)
N1A—Zn—O1A	96.73 (5)
N1B—Zn—O1A	114.34 (5)