(Acetato-κO)(2-bromo-6-{[3-(dimethyl­aza­nium­yl)propyl­imino-κN]meth­yl}phenolato-κO)(thio­cyanato-κN)zinc

Han, C.-L.

doi:10.1107/S1600536812017564

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page m677

doi:10.1107/S1600536812017564

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(Acetato-κO)(2-bromo-6-{[3-(dimethylazaniumyl)propylimino-κN]methyl}phenolato-κO)(thiocyanato-κN)zinc

Cheng-Li Han ^a ^*

^aCollege of Chemistry and Chemical Engineering, Qiqihar University, Qiqihar 161006, People's Republic of China
^*Correspondence e-mail: chengli_han@126.com

(Received 10 April 2012; accepted 20 April 2012; online 25 April 2012)

In the title compound, [Zn(CH₃COO)(NCS)(C₁₂H₁₇BrN₂O)], the Zn^II atom is four-coordinated in a distorted tetrahedral geometry, binding to a phenolate O and an imine N atom of the Schiff base ligand, the O atom of an acetate ligand and one thiocyanate N atom. In the crystal, molecules are linked via pairs of N—H⋯O hydrogen bonds, forming inversion dimers.

Related literature

For a zinc Schiff base complex reported previously by the author, see: Han (2009 ). For related zinc complexes, see: Ali et al. (2008 ); You (2005 ); Zhu & Yang (2008 ).

Experimental

Crystal data

[Zn(C₂H₃O₂)(NCS)(C₁₂H₁₇BrN₂O)]
M_r = 467.68
Triclinic, $[P \overline 1]$
a = 9.3091 (6) Å
b = 10.2687 (6) Å
c = 11.8353 (7) Å
α = 66.299 (2)°
β = 79.891 (2)°
γ = 88.122 (2)°
V = 1018.96 (11) Å³
Z = 2
Mo Kα radiation
μ = 3.28 mm⁻¹
T = 298 K
0.17 × 0.15 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.605, T_max = 0.639
9684 measured reflections
3720 independent reflections
3021 reflections with I > 2σ(I)
R_int = 0.129

Refinement

R[F² > 2σ(F²)] = 0.072
wR(F²) = 0.201
S = 1.07
3720 reflections
220 parameters
H-atom parameters constrained
Δρ_max = 1.32 e Å⁻³
Δρ_min = −0.61 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O3ⁱ	0.91	1.81	2.703 (6)	168
Symmetry code: (i) -x+1, -y, -z.

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); 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 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812017564/su2407sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812017564/su2407Isup2.hkl

checkCIF report

Comment top

Continuing our research into the synthesis of Schiff base zinc(II) complexes (Han, 2009), we report herein on the crystal structure of the title complex. It was synthesized by the reaction of equimolar quantities of 3-bromosalicyaldehyde, N,N-dimethylpropane-1,3-diamine, ammonium thiocyanate, and zinc acetate in methanol.

In the title complex (Fig. 1), the Zn^II atom is four-coordinate in a tetrahedral geometry, with one O and one imine N atoms of the Schiff base ligand, one O atom of an acetate ligand, and one thiocyanate N atom. The tetrahedral geometry is severely distorted, as evidenced by the coordinate bond lengths [1.931 (4) - 1.994 (5) Å] and bond angles [96.3 (2) - 124.1 (2)°]. They are however comparable to those in similar zinc(II) complexes (Ali et al., 2008; You, 2005; Zhu & Yang, 2008).

In the crystal, molecules are linked through N–H···O hydrogen bonds to form inversion dimers (Table 1 and Fig. 2).

Related literature top

For a Schiff base–zinc(II) complex reported previously by the author, see: Han (2009). For the structures of related zinc(II) complexes, see: Ali et al. (2008); You (2005); Zhu & Yang (2008).

Experimental top

Equimolar quantities (1.0 mmol each) of 3-bromosalicyaldehyde, N,N-dimethylpropane-1,3-diamine, ammonium thiocyanate, and zinc acetate were mixed in methanol. The mixture was stirred at reflux for 30 min and filtered. The filtrate was left to evaporate slowly for a few days, yielding colourless block-like crystals.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title complex, showing 30% probability displacement ellipsoids and the atom-numbering.
	Fig. 2. The crystal packing of the title complex viewed along the a axis, showing the formation of the inversion dimers. The N-H···O hydrogen bonds are shown as dashed lines.

(Acetato-κO)(2-bromo-6-{[3-(dimethylazaniumyl)propylimino- κN]methyl}phenolato-κO)(thiocyanato-κN)zinc top

Crystal data top

[Zn(C₂H₃O₂)(NCS)(C₁₂H₁₇BrN₂O)]	Z = 2
M_r = 467.68	F(000) = 472
Triclinic, P1	D_x = 1.524 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.3091 (6) Å	Cell parameters from 5991 reflections
b = 10.2687 (6) Å	θ = 2.2–27.9°
c = 11.8353 (7) Å	µ = 3.28 mm⁻¹
α = 66.299 (2)°	T = 298 K
β = 79.891 (2)°	Block, colourless
γ = 88.122 (2)°	0.17 × 0.15 × 0.15 mm
V = 1018.96 (11) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	3720 independent reflections
Radiation source: fine-focus sealed tube	3021 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.129
ω scans	θ_max = 25.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.605, T_max = 0.639	k = −12→12
9684 measured reflections	l = −14→14

Refinement top

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)] = 0.072	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.201	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0811P)² + 2.5468P] where P = (F_o² + 2F_c²)/3
3720 reflections	(Δ/σ)_max < 0.001
220 parameters	Δρ_max = 1.32 e Å⁻³
0 restraints	Δρ_min = −0.61 e Å⁻³

Crystal data top

[Zn(C₂H₃O₂)(NCS)(C₁₂H₁₇BrN₂O)]	γ = 88.122 (2)°
M_r = 467.68	V = 1018.96 (11) Å³
Triclinic, P1	Z = 2
a = 9.3091 (6) Å	Mo Kα radiation
b = 10.2687 (6) Å	µ = 3.28 mm⁻¹
c = 11.8353 (7) Å	T = 298 K
α = 66.299 (2)°	0.17 × 0.15 × 0.15 mm
β = 79.891 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3720 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3021 reflections with I > 2σ(I)
T_min = 0.605, T_max = 0.639	R_int = 0.129
9684 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.072	0 restraints
wR(F²) = 0.201	H-atom parameters constrained
S = 1.07	Δρ_max = 1.32 e Å⁻³
3720 reflections	Δρ_min = −0.61 e Å⁻³
220 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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

	x	y	z	U_iso*/U_eq
Zn1	0.71920 (7)	0.16314 (7)	0.17582 (7)	0.0445 (3)
Br1	0.86805 (11)	0.41595 (10)	0.41002 (10)	0.0872 (4)
N1	0.5145 (5)	0.0900 (5)	0.2551 (5)	0.0429 (11)
N2	0.2396 (5)	0.2871 (5)	−0.0322 (5)	0.0436 (11)
H2	0.2172	0.2258	−0.0653	0.052*
N3	0.7308 (6)	0.2974 (7)	0.0016 (6)	0.0642 (15)
O1	0.7416 (5)	0.2599 (5)	0.2823 (5)	0.0599 (12)
O2	0.8893 (5)	0.0442 (5)	0.1972 (5)	0.0598 (12)
O3	0.7888 (5)	−0.0922 (5)	0.1276 (5)	0.0565 (11)
S1	0.7396 (3)	0.5055 (2)	−0.2352 (2)	0.0807 (6)
C1	0.5007 (7)	0.1983 (6)	0.4068 (5)	0.0478 (14)
C2	0.6446 (7)	0.2621 (6)	0.3737 (6)	0.0475 (14)
C3	0.6772 (9)	0.3331 (6)	0.4473 (7)	0.0589 (17)
C4	0.5794 (11)	0.3442 (7)	0.5422 (7)	0.070 (2)
H4	0.6069	0.3901	0.5891	0.084*
C5	0.4342 (11)	0.2853 (8)	0.5701 (7)	0.075 (2)
H5	0.3646	0.2963	0.6320	0.090*
C6	0.4007 (9)	0.2134 (7)	0.5044 (6)	0.0640 (19)
H6	0.3073	0.1718	0.5243	0.077*
C7	0.4463 (7)	0.1182 (6)	0.3462 (6)	0.0473 (14)
H7	0.3503	0.0826	0.3767	0.057*
C8	0.4325 (7)	0.0049 (6)	0.2105 (6)	0.0486 (14)
H8A	0.3428	−0.0341	0.2699	0.058*
H8B	0.4903	−0.0740	0.2065	0.058*
C9	0.3960 (6)	0.0940 (6)	0.0817 (6)	0.0430 (13)
H9A	0.4839	0.1438	0.0248	0.052*
H9B	0.3587	0.0321	0.0485	0.052*
C10	0.2827 (6)	0.2011 (7)	0.0899 (6)	0.0468 (14)
H10A	0.1967	0.1508	0.1495	0.056*
H10B	0.3217	0.2641	0.1210	0.056*
C11	0.3592 (8)	0.3865 (8)	−0.1235 (8)	0.0659 (19)
H11A	0.3239	0.4437	−0.1991	0.099*
H11B	0.4392	0.3329	−0.1423	0.099*
H11C	0.3916	0.4470	−0.0879	0.099*
C12	0.1071 (7)	0.3664 (8)	−0.0167 (9)	0.074 (2)
H12A	0.0287	0.3006	0.0379	0.110*
H12B	0.0797	0.4187	−0.0969	0.110*
H12C	0.1269	0.4314	0.0192	0.110*
C13	0.7343 (6)	0.3843 (7)	−0.0990 (6)	0.0471 (14)
C14	0.8872 (6)	−0.0647 (6)	0.1725 (6)	0.0418 (13)
C15	1.0122 (8)	−0.1603 (8)	0.2014 (8)	0.068 (2)
H15A	0.9755	−0.2559	0.2535	0.102*
H15B	1.0720	−0.1286	0.2445	0.102*
H15C	1.0694	−0.1579	0.1247	0.102*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0424 (4)	0.0461 (4)	0.0530 (5)	0.0063 (3)	−0.0081 (3)	−0.0288 (3)
Br1	0.1033 (7)	0.0773 (6)	0.1037 (7)	−0.0066 (5)	−0.0388 (6)	−0.0506 (5)
N1	0.041 (2)	0.038 (2)	0.050 (3)	0.0034 (19)	−0.012 (2)	−0.017 (2)
N2	0.036 (2)	0.036 (2)	0.073 (3)	0.0091 (18)	−0.018 (2)	−0.034 (2)
N3	0.047 (3)	0.075 (4)	0.072 (4)	0.007 (3)	−0.010 (3)	−0.031 (3)
O1	0.056 (2)	0.069 (3)	0.072 (3)	−0.001 (2)	−0.008 (2)	−0.047 (3)
O2	0.053 (2)	0.057 (3)	0.095 (4)	0.016 (2)	−0.027 (2)	−0.052 (3)
O3	0.052 (2)	0.055 (2)	0.082 (3)	0.0154 (19)	−0.024 (2)	−0.044 (2)
S1	0.0938 (15)	0.0725 (13)	0.0613 (12)	−0.0063 (11)	−0.0086 (11)	−0.0134 (10)
C1	0.067 (4)	0.038 (3)	0.039 (3)	0.013 (3)	−0.012 (3)	−0.017 (2)
C2	0.062 (4)	0.039 (3)	0.049 (3)	0.013 (3)	−0.014 (3)	−0.024 (3)
C3	0.088 (5)	0.037 (3)	0.057 (4)	0.013 (3)	−0.023 (4)	−0.020 (3)
C4	0.127 (7)	0.044 (3)	0.049 (4)	0.018 (4)	−0.021 (4)	−0.027 (3)
C5	0.112 (7)	0.058 (4)	0.051 (4)	0.016 (4)	0.001 (4)	−0.025 (3)
C6	0.084 (5)	0.047 (3)	0.051 (4)	0.011 (3)	0.001 (3)	−0.015 (3)
C7	0.047 (3)	0.040 (3)	0.048 (3)	0.002 (2)	−0.004 (3)	−0.012 (3)
C8	0.046 (3)	0.040 (3)	0.062 (4)	0.003 (2)	−0.011 (3)	−0.022 (3)
C9	0.046 (3)	0.041 (3)	0.057 (3)	0.012 (2)	−0.020 (3)	−0.032 (3)
C10	0.042 (3)	0.051 (3)	0.061 (4)	0.012 (2)	−0.010 (3)	−0.035 (3)
C11	0.061 (4)	0.051 (4)	0.079 (5)	−0.003 (3)	−0.008 (4)	−0.021 (4)
C12	0.048 (3)	0.063 (4)	0.130 (7)	0.027 (3)	−0.028 (4)	−0.057 (5)
C13	0.038 (3)	0.053 (3)	0.055 (4)	0.002 (2)	−0.005 (3)	−0.027 (3)
C14	0.040 (3)	0.040 (3)	0.052 (3)	0.010 (2)	−0.007 (2)	−0.026 (3)
C15	0.058 (4)	0.059 (4)	0.104 (6)	0.023 (3)	−0.031 (4)	−0.045 (4)

Geometric parameters (Å, º) top

Zn1—O1	1.931 (4)	C5—C6	1.345 (11)
Zn1—N3	1.952 (7)	C5—H5	0.9300
Zn1—O2	1.957 (4)	C6—H6	0.9300
Zn1—N1	1.994 (5)	C7—H7	0.9300
Br1—C3	1.897 (8)	C8—C9	1.523 (9)
N1—C7	1.284 (8)	C8—H8A	0.9700
N1—C8	1.476 (8)	C8—H8B	0.9700
N2—C10	1.477 (8)	C9—C10	1.518 (7)
N2—C12	1.482 (7)	C9—H9A	0.9700
N2—C11	1.488 (8)	C9—H9B	0.9700
N2—H2	0.9100	C10—H10A	0.9700
N3—C13	1.161 (9)	C10—H10B	0.9700
O1—C2	1.289 (7)	C11—H11A	0.9600
O2—C14	1.265 (7)	C11—H11B	0.9600
O3—C14	1.229 (7)	C11—H11C	0.9600
S1—C13	1.586 (7)	C12—H12A	0.9600
C1—C6	1.407 (9)	C12—H12B	0.9600
C1—C2	1.430 (9)	C12—H12C	0.9600
C1—C7	1.442 (9)	C14—C15	1.493 (8)
C2—C3	1.414 (9)	C15—H15A	0.9600
C3—C4	1.356 (11)	C15—H15B	0.9600
C4—C5	1.428 (13)	C15—H15C	0.9600
C4—H4	0.9300

O1—Zn1—N3	111.3 (2)	N1—C8—H8A	109.3
O1—Zn1—O2	100.4 (2)	C9—C8—H8A	109.3
N3—Zn1—O2	111.2 (2)	N1—C8—H8B	109.3
O1—Zn1—N1	96.3 (2)	C9—C8—H8B	109.3
N3—Zn1—N1	111.3 (2)	H8A—C8—H8B	108.0
O2—Zn1—N1	124.1 (2)	C10—C9—C8	110.5 (5)
C7—N1—C8	116.7 (5)	C10—C9—H9A	109.5
C7—N1—Zn1	121.0 (4)	C8—C9—H9A	109.5
C8—N1—Zn1	122.2 (4)	C10—C9—H9B	109.5
C10—N2—C12	111.3 (5)	C8—C9—H9B	109.5
C10—N2—C11	112.8 (5)	H9A—C9—H9B	108.1
C12—N2—C11	110.2 (5)	N2—C10—C9	112.7 (5)
C10—N2—H2	107.4	N2—C10—H10A	109.1
C12—N2—H2	107.4	C9—C10—H10A	109.1
C11—N2—H2	107.4	N2—C10—H10B	109.1
C13—N3—Zn1	175.3 (6)	C9—C10—H10B	109.1
C2—O1—Zn1	125.7 (4)	H10A—C10—H10B	107.8
C14—O2—Zn1	117.7 (4)	N2—C11—H11A	109.5
C6—C1—C2	119.7 (6)	N2—C11—H11B	109.5
C6—C1—C7	115.5 (6)	H11A—C11—H11B	109.5
C2—C1—C7	124.8 (5)	N2—C11—H11C	109.5
O1—C2—C3	119.9 (6)	H11A—C11—H11C	109.5
O1—C2—C1	124.3 (5)	H11B—C11—H11C	109.5
C3—C2—C1	115.8 (6)	N2—C12—H12A	109.5
C4—C3—C2	123.3 (7)	N2—C12—H12B	109.5
C4—C3—Br1	119.1 (6)	H12A—C12—H12B	109.5
C2—C3—Br1	117.6 (5)	N2—C12—H12C	109.5
C3—C4—C5	120.0 (7)	H12A—C12—H12C	109.5
C3—C4—H4	120.0	H12B—C12—H12C	109.5
C5—C4—H4	120.0	N3—C13—S1	178.7 (6)
C6—C5—C4	118.3 (7)	O3—C14—O2	122.9 (5)
C6—C5—H5	120.9	O3—C14—C15	120.9 (5)
C4—C5—H5	120.9	O2—C14—C15	116.2 (6)
C5—C6—C1	122.9 (8)	C14—C15—H15A	109.5
C5—C6—H6	118.6	C14—C15—H15B	109.5
C1—C6—H6	118.6	H15A—C15—H15B	109.5
N1—C7—C1	127.8 (6)	C14—C15—H15C	109.5
N1—C7—H7	116.1	H15A—C15—H15C	109.5
C1—C7—H7	116.1	H15B—C15—H15C	109.5
N1—C8—C9	111.6 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3ⁱ	0.91	1.81	2.703 (6)	168

Symmetry code: (i) −x+1, −y, −z.

Experimental details

Crystal data
Chemical formula	[Zn(C₂H₃O₂)(NCS)(C₁₂H₁₇BrN₂O)]
M_r	467.68
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	9.3091 (6), 10.2687 (6), 11.8353 (7)
α, β, γ (°)	66.299 (2), 79.891 (2), 88.122 (2)
V (Å³)	1018.96 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	3.28
Crystal size (mm)	0.17 × 0.15 × 0.15

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.605, 0.639
No. of measured, independent and observed [I > 2σ(I)] reflections	9684, 3720, 3021
R_int	0.129
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.072, 0.201, 1.07
No. of reflections	3720
No. of parameters	220
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.32, −0.61

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3ⁱ	0.91	1.81	2.703 (6)	168

Symmetry code: (i) −x+1, −y, −z.

Acknowledgements

The author acknowledges Qiqihar University for a research grant.

References

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page m677

doi:10.1107/S1600536812017564

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

(Acetato-κO)(2-bromo-6-{[3-(di­methyl­aza­nium­yl)propyl­imino-κN]meth­yl}phenolato-κO)(thio­cyanato-κN)zinc

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

(Acetato-κO)(2-bromo-6-{[3-(dimethylazaniumyl)propylimino-κN]methyl}phenolato-κO)(thiocyanato-κN)zinc