Bis(acetato-κO)bis-(4,5-dimethyl-benzene-1,2-diamine-κN)zinc.

The structure of the title compound, [Zn(CH(3)COO)(2)(C(8)H(12)N(2))(2)], has one half molecule in the asymmetric unit. The Zn(II) atom is situated on a twofold rotation axis and is tetrahedrally coordinated by two N and two O atoms. The crystal packing displays inter-molecular N-H⋯O hydrogen bonds and intra-molecular N-H⋯O and N-H⋯N hydrogen bonding.

Related literature

For the role of complexes in biochemical systems with zinc in tetrahedral coordination, see: Parkin (2004 ▶); Maret & Li (2009 ▶). For the structure of the corresponding 1,2-diamino­benzene complex, see: Mei et al. (2009 ▶). For an example of a structurally characterized tetramine complex with zinc in tetrahedral coordination, see: Xu et al. (1998 ▶). For an example carboxyl­ate coordination in a similar complex, see: Harding (2001 ▶).

Experimental

Crystal data

[Zn(C2H3O2)2(C8H12N2)2]

M = 455.85

Monoclinic,

a = 18.432 (3) Å

b = 4.7414 (6) Å

c = 25.740 (4) Å

β = 92.284 (4)°

V = 2247.8 (5) Å3

Z = 4

Mo Kα radiation

μ = 1.12 mm−1

T = 200 K

0.80 × 0.30 × 0.20 mm

Data collection

Bruker SMART X2S benchtop diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008b ▶) T min = 0.467, T max = 0.806

11403 measured reflections

1986 independent reflections

1905 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.094

S = 1.12

1986 reflections

151 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.67 e Å−3

Δρmin = −0.37 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008a ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008a ▶); molecular graphics: XSHELL (Bruker, 2004 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681203036X/bv2208sup1.cif

Supplementary material file. DOI: 10.1107/S160053681203036X/bv2208Isup2.cdx

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681203036X/bv2208Isup3.hkl

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

[Zn(C2H3O2)2(C8H12N2)2]	F(000) = 960
Mr = 455.85	Dx = 1.347 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C2yc	Cell parameters from 5876 reflections
a = 18.432 (3) Å	θ = 2.7–25.0°
b = 4.7414 (6) Å	µ = 1.12 mm−1
c = 25.740 (4) Å	T = 200 K
β = 92.284 (4)°	Plate, colourless
V = 2247.8 (5) Å3	0.80 × 0.30 × 0.20 mm
Z = 4

Bruker SMART X2S benchtop diffractometer	1986 independent reflections
Radiation source: fine-focus sealed tube	1905 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.046
ω scans	θmax = 25.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008b)	h = −21→21
Tmin = 0.467, Tmax = 0.806	k = −5→5
11403 measured reflections	l = −28→30

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ2(Fo2) + (0.0434P)2 + 4.1592P] where P = (Fo2 + 2Fc2)/3
1986 reflections	(Δ/σ)max < 0.001
151 parameters	Δρmax = 0.67 e Å−3
0 restraints	Δρmin = −0.37 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
Zn1	0.5000	0.21781 (8)	0.2500	0.02608 (16)
O1	0.53194 (10)	0.4948 (4)	0.30352 (6)	0.0343 (4)
O2	0.60458 (11)	0.1492 (4)	0.33024 (7)	0.0421 (5)
N1	0.56934 (12)	−0.0427 (5)	0.21196 (8)	0.0281 (5)
N2	0.69849 (13)	0.2531 (6)	0.23902 (9)	0.0360 (6)
C1	0.60972 (12)	0.0974 (5)	0.17273 (9)	0.0262 (5)
C2	0.67121 (13)	0.2524 (5)	0.18723 (10)	0.0279 (6)
C3	0.70681 (14)	0.3968 (6)	0.14856 (10)	0.0344 (6)
H3	0.7496	0.4999	0.1579	0.041*
C4	0.68215 (14)	0.3954 (7)	0.09706 (10)	0.0364 (6)
C5	0.61975 (15)	0.2423 (7)	0.08302 (10)	0.0383 (7)
C6	0.58503 (14)	0.0931 (7)	0.12132 (10)	0.0351 (6)
H6	0.5431	−0.0149	0.1119	0.042*
C7	0.5892 (2)	0.2368 (9)	0.02749 (12)	0.0659 (12)
H7A	0.5444	0.1254	0.0258	0.099*
H7B	0.6248	0.1515	0.0049	0.099*
H7C	0.5787	0.4298	0.0159	0.099*
C8	0.72326 (19)	0.5613 (8)	0.05768 (12)	0.0553 (9)
H8A	0.7708	0.6160	0.0729	0.083*
H8B	0.6957	0.7310	0.0478	0.083*
H8C	0.7300	0.4446	0.0268	0.083*
C9	0.57583 (14)	0.3768 (6)	0.33792 (9)	0.0308 (6)
C10	0.58890 (18)	0.5363 (7)	0.38778 (11)	0.0488 (8)
H10A	0.6249	0.4360	0.4099	0.073*
H10B	0.5433	0.5516	0.4059	0.073*
H10C	0.6070	0.7256	0.3801	0.073*
H1A	0.5413 (19)	−0.167 (7)	0.1990 (12)	0.045 (9)*
H1B	0.5973 (17)	−0.120 (7)	0.2345 (12)	0.039 (8)*
H2A	0.6658 (18)	0.234 (6)	0.2628 (12)	0.039 (9)*
H2B	0.7263 (18)	0.383 (8)	0.2448 (12)	0.042 (9)*

	U11	U22	U33	U12	U13	U23
Zn1	0.0257 (2)	0.0218 (2)	0.0310 (2)	0.000	0.00465 (15)	0.000
O1	0.0391 (10)	0.0294 (10)	0.0338 (9)	0.0044 (8)	−0.0066 (7)	−0.0022 (8)
O2	0.0462 (12)	0.0404 (13)	0.0398 (10)	0.0137 (10)	0.0034 (8)	0.0026 (9)
N1	0.0235 (10)	0.0279 (13)	0.0330 (11)	−0.0022 (10)	0.0030 (9)	0.0003 (9)
N2	0.0251 (11)	0.0492 (17)	0.0336 (12)	−0.0046 (11)	−0.0011 (10)	0.0021 (10)
C1	0.0210 (11)	0.0258 (13)	0.0323 (12)	0.0021 (10)	0.0053 (9)	−0.0003 (10)
C2	0.0213 (12)	0.0306 (15)	0.0319 (12)	0.0030 (10)	0.0022 (9)	−0.0002 (10)
C3	0.0232 (12)	0.0393 (16)	0.0410 (14)	−0.0057 (12)	0.0055 (10)	−0.0013 (12)
C4	0.0315 (14)	0.0424 (17)	0.0360 (13)	0.0002 (13)	0.0101 (11)	0.0045 (12)
C5	0.0327 (14)	0.0525 (19)	0.0297 (13)	−0.0007 (13)	0.0026 (11)	0.0009 (12)
C6	0.0260 (13)	0.0440 (17)	0.0355 (13)	−0.0073 (12)	0.0033 (10)	−0.0067 (12)
C7	0.053 (2)	0.110 (4)	0.0338 (16)	−0.014 (2)	−0.0010 (14)	0.0017 (18)
C8	0.0550 (19)	0.066 (2)	0.0455 (17)	−0.0125 (18)	0.0163 (14)	0.0110 (16)
C9	0.0298 (13)	0.0311 (15)	0.0314 (12)	−0.0015 (11)	0.0017 (10)	0.0037 (11)
C10	0.066 (2)	0.0427 (19)	0.0368 (15)	0.0084 (16)	−0.0131 (14)	−0.0038 (13)

Zn1—O1	1.9759 (18)	C3—H3	0.9500
Zn1—O1i	1.9759 (18)	C4—C5	1.395 (4)
Zn1—N1	2.054 (2)	C4—C8	1.511 (4)
Zn1—N1i	2.054 (2)	C5—C6	1.390 (4)
O1—C9	1.302 (3)	C5—C7	1.516 (4)
O2—C9	1.222 (3)	C6—H6	0.9500
N1—C1	1.441 (3)	C7—H7A	0.9800
N1—H1A	0.84 (4)	C7—H7B	0.9800
N1—H1B	0.84 (3)	C7—H7C	0.9800
N2—C2	1.406 (3)	C8—H8A	0.9800
N2—H2A	0.88 (3)	C8—H8B	0.9800
N2—H2B	0.81 (4)	C8—H8C	0.9800
C1—C6	1.382 (3)	C9—C10	1.501 (4)
C1—C2	1.389 (4)	C10—H10A	0.9800
C2—C3	1.394 (4)	C10—H10B	0.9800
C3—C4	1.384 (4)	C10—H10C	0.9800
O1—Zn1—O1i	96.70 (10)	C6—C5—C4	118.6 (2)
O1—Zn1—N1	123.94 (8)	C6—C5—C7	119.7 (3)
O1i—Zn1—N1	103.95 (8)	C4—C5—C7	121.7 (3)
O1—Zn1—N1i	103.95 (8)	C1—C6—C5	121.9 (2)
O1i—Zn1—N1i	123.94 (8)	C1—C6—H6	119.1
N1—Zn1—N1i	106.06 (13)	C5—C6—H6	119.1
C9—O1—Zn1	110.40 (17)	C5—C7—H7A	109.5
C1—N1—Zn1	113.93 (17)	C5—C7—H7B	109.5
C1—N1—H1A	112 (2)	H7A—C7—H7B	109.5
Zn1—N1—H1A	103 (2)	C5—C7—H7C	109.5
C1—N1—H1B	111 (2)	H7A—C7—H7C	109.5
Zn1—N1—H1B	108 (2)	H7B—C7—H7C	109.5
H1A—N1—H1B	109 (3)	C4—C8—H8A	109.5
C2—N2—H2A	115 (2)	C4—C8—H8B	109.5
C2—N2—H2B	112 (2)	H8A—C8—H8B	109.5
H2A—N2—H2B	113 (3)	C4—C8—H8C	109.5
C6—C1—C2	119.9 (2)	H8A—C8—H8C	109.5
C6—C1—N1	120.3 (2)	H8B—C8—H8C	109.5
C2—C1—N1	119.6 (2)	O2—C9—O1	122.1 (2)
C1—C2—C3	118.1 (2)	O2—C9—C10	121.8 (2)
C1—C2—N2	120.9 (2)	O1—C9—C10	116.1 (2)
C3—C2—N2	121.0 (2)	C9—C10—H10A	109.5
C4—C3—C2	122.4 (2)	C9—C10—H10B	109.5
C4—C3—H3	118.8	H10A—C10—H10B	109.5
C2—C3—H3	118.8	C9—C10—H10C	109.5
C3—C4—C5	119.1 (2)	H10A—C10—H10C	109.5
C3—C4—C8	119.1 (3)	H10B—C10—H10C	109.5
C5—C4—C8	121.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ii	0.84 (4)	2.10 (4)	2.897 (3)	158 (3)
N2—H2A···O2	0.88 (3)	2.15 (3)	3.013 (3)	168 (3)
N2—H2B···N2iii	0.81 (4)	2.26 (4)	3.076 (3)	179 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.84 (4)	2.10 (4)	2.897 (3)	158 (3)
N2—H2A⋯O2	0.88 (3)	2.15 (3)	3.013 (3)	168 (3)
N2—H2B⋯N2ii	0.81 (4)	2.26 (4)	3.076 (3)	179 (3)

Symmetry codes: (i) ; (ii) .