A dinuclear zinc complex with (E)-4-dimethyl-amino-N'-(2-hy-droxy-benzyl-idene)benzohydrazide.

The title compound, bis-[μ-(E)-2-({2-[4-(dimethyl-amino)-benzo-yl]hydrazinyl-idene}meth-yl)phenolato]bis-[formato-zinc], [Zn(2)(C(16)H(16)N(3)O(2))(2)(CHO(2))(2)], is a dinuclear Zn(II) complex containing two Zn(II) cations, two monovalent anions of a Schiff base ligand, 4-dimethyl-amino-N'-(2-hy-droxy-benzyl-idene)benzohydrazide (L), and two formate ions. Each Zn(II) atom chelates with the hy-droxy O atom of salicyl-aldehyde, the imine N atom, the carbonyl O atom, the formate carboxyl-ate O atom and the hy-droxy O atom of the salicyl-aldehyde moiety in a symmetry-related unit. The five-coordinate Zn(II) atoms form a dimeric centrosymmetric unit with a central parallelepiped Zn(2)O(2) core and parallel faces derived from the Schiff base ligands. The crystal packing is stabilized by inter-molecular N-H⋯O hydrogen bonds between the amide N atom and the formate carboxyl-ate O atom.

Related literature

For details of Zn complexes and related applications, see: Shamsipur et al. (2001 ▶); Cametti et al. (2008 ▶); Winter et al. (2009 ▶); Shi et al. (2009 ▶); Rai et al. (2009 ▶). For potential applications in luminescence materials, see: Erxleben (2001 ▶). For recent advances in biosensory and medicinal therapeutic applications of ZnII complexes, see: Drewry & Gunning (2011 ▶). For other applications of Schiff base–zinc complexes, see: Costamagna et al. (1992 ▶); Sunatsuki et al. (2002 ▶); Jiang et al. (2010 ▶); Li et al. (2010 ▶). For details of the synthesis of the Schiff base ligand, see: Pouralimardan et al. (2007 ▶). For related literature on zinc complex applications, see: Consiglio et al. (2010 ▶); Kwok et al. (2004 ▶).

Experimental

Crystal data

[Zn2(C16H16N3O2)2(CHO2)2]

M = 785.41

Monoclinic,

a = 14.556 (3) Å

b = 6.7607 (14) Å

c = 17.085 (3) Å

β = 101.63 (3)°

V = 1646.8 (6) Å3

Z = 2

Mo Kα radiation

μ = 1.52 mm−1

T = 173 K

0.10 × 0.10 × 0.08 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.863, T max = 0.888

13433 measured reflections

3213 independent reflections

2679 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.077

S = 1.07

3213 reflections

228 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.30 e Å−3

Data collection: RAPID-AUTO (Rigaku, 2004 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; 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: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811014462/jj2088sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811014462/jj2088Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811014462/jj2088Isup3.cdx

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

[Zn2(C16H16N3O2)2(CHO2)2]	F(000) = 808
Mr = 785.41	Dx = 1.584 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 11481 reflections
a = 14.556 (3) Å	θ = 6.1–55.0°
b = 6.7607 (14) Å	µ = 1.52 mm−1
c = 17.085 (3) Å	T = 173 K
β = 101.63 (3)°	Block, yellow
V = 1646.8 (6) Å3	0.10 × 0.10 × 0.08 mm
Z = 2

Rigaku R-AXIS RAPID diffractometer	3213 independent reflections
Radiation source: Rotating anode	2679 reflections with I > 2σ(I)
graphite	Rint = 0.032
ω scans	θmax = 26.0°, θmin = 3.3°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −17→17
Tmin = 0.863, Tmax = 0.888	k = −8→8
13433 measured reflections	l = −21→21

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0452P)2 + 0.0838P] where P = (Fo2 + 2Fc2)/3
3213 reflections	(Δ/σ)max = 0.002
228 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

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.

	x	y	z	Uiso*/Ueq
Zn1	0.604524 (15)	0.57545 (3)	0.527904 (16)	0.03564 (10)
O1	0.47575 (10)	0.5761 (2)	0.56269 (10)	0.0401 (4)
N2	0.68239 (11)	0.9705 (2)	0.53175 (12)	0.0381 (4)
H8	0.6959	1.0948	0.5444	0.046*
N1	0.60914 (11)	0.8734 (2)	0.55588 (11)	0.0344 (4)
O2	0.71192 (10)	0.6870 (2)	0.47370 (10)	0.0436 (4)
C11	0.90778 (14)	1.2366 (3)	0.44114 (14)	0.0418 (5)
H11	0.9247	1.3710	0.4520	0.050*
C9	0.80890 (13)	0.9595 (3)	0.45818 (13)	0.0339 (5)
C12	0.95679 (14)	1.1247 (3)	0.39372 (14)	0.0378 (5)
C13	0.92810 (15)	0.9259 (3)	0.37917 (15)	0.0419 (5)
H13	0.9591	0.8446	0.3472	0.050*
C8	0.73176 (13)	0.8649 (3)	0.48804 (13)	0.0347 (5)
C6	0.48425 (14)	0.8912 (3)	0.62988 (14)	0.0378 (5)
N3	1.02861 (13)	1.2013 (3)	0.36293 (13)	0.0476 (5)
C10	0.83602 (14)	1.1570 (3)	0.47224 (14)	0.0385 (5)
H10	0.8042	1.2374	0.5039	0.046*
C1	0.44444 (13)	0.7007 (3)	0.61235 (13)	0.0355 (5)
C7	0.56179 (15)	0.9695 (3)	0.59851 (15)	0.0414 (5)
H7	0.5789	1.1034	0.6106	0.050*
C14	0.85623 (15)	0.8488 (3)	0.41056 (15)	0.0418 (5)
H14	0.8383	0.7151	0.3993	0.050*
C15	1.08257 (17)	1.0784 (4)	0.31949 (17)	0.0560 (7)
H15A	1.1347	1.1554	0.3068	0.084*
H15B	1.0422	1.0322	0.2699	0.084*
H15C	1.1074	0.9642	0.3524	0.084*
C16	1.06386 (17)	1.3985 (3)	0.38441 (18)	0.0547 (6)
H16A	1.0112	1.4911	0.3788	0.082*
H16B	1.1058	1.4389	0.3490	0.082*
H16C	1.0985	1.3987	0.4399	0.082*
C2	0.37002 (15)	0.6489 (4)	0.64826 (15)	0.0461 (6)
H2	0.3428	0.5212	0.6387	0.055*
C3	0.33486 (16)	0.7778 (4)	0.69733 (16)	0.0540 (6)
H3	0.2835	0.7380	0.7202	0.065*
C5	0.44609 (16)	1.0176 (4)	0.68003 (16)	0.0504 (6)
H5	0.4723	1.1458	0.6909	0.060*
C4	0.37272 (17)	0.9632 (4)	0.71382 (16)	0.0559 (7)
H4	0.3483	1.0512	0.7479	0.067*
O3	0.68177 (10)	0.3641 (2)	0.58935 (10)	0.0429 (4)
O4	0.71583 (15)	0.5810 (3)	0.68721 (13)	0.0722 (6)
C17	0.72061 (16)	0.4179 (3)	0.65971 (16)	0.0455 (6)
H17	0.7563	0.3216	0.6933	0.055*

	U11	U22	U33	U12	U13	U23
Zn1	0.03384 (15)	0.02593 (14)	0.04950 (19)	−0.00573 (9)	0.01398 (11)	−0.00385 (10)
O1	0.0353 (7)	0.0404 (8)	0.0478 (10)	−0.0092 (6)	0.0162 (7)	−0.0117 (7)
N2	0.0372 (9)	0.0266 (8)	0.0540 (13)	−0.0070 (7)	0.0180 (9)	−0.0025 (8)
N1	0.0336 (8)	0.0281 (8)	0.0432 (11)	−0.0063 (7)	0.0117 (8)	0.0007 (7)
O2	0.0469 (8)	0.0292 (7)	0.0604 (11)	−0.0115 (6)	0.0246 (8)	−0.0085 (7)
C11	0.0446 (11)	0.0323 (10)	0.0517 (15)	−0.0104 (9)	0.0171 (10)	−0.0037 (10)
C9	0.0335 (10)	0.0320 (10)	0.0368 (13)	−0.0043 (8)	0.0084 (9)	0.0010 (8)
C12	0.0349 (10)	0.0399 (11)	0.0396 (14)	−0.0026 (9)	0.0097 (9)	0.0037 (9)
C13	0.0449 (11)	0.0382 (11)	0.0469 (15)	−0.0002 (9)	0.0194 (11)	−0.0060 (10)
C8	0.0329 (9)	0.0319 (10)	0.0389 (13)	−0.0036 (8)	0.0067 (9)	0.0014 (9)
C6	0.0371 (10)	0.0364 (10)	0.0416 (14)	−0.0006 (9)	0.0124 (9)	−0.0042 (9)
N3	0.0465 (10)	0.0476 (10)	0.0548 (14)	−0.0094 (9)	0.0250 (10)	−0.0018 (9)
C10	0.0410 (11)	0.0333 (10)	0.0443 (14)	−0.0055 (9)	0.0159 (10)	−0.0053 (9)
C1	0.0315 (9)	0.0402 (11)	0.0347 (13)	−0.0008 (9)	0.0065 (9)	−0.0020 (9)
C7	0.0427 (11)	0.0305 (10)	0.0536 (16)	−0.0054 (9)	0.0161 (11)	−0.0061 (10)
C14	0.0459 (11)	0.0307 (10)	0.0511 (15)	−0.0066 (9)	0.0150 (11)	−0.0037 (10)
C15	0.0486 (13)	0.0675 (16)	0.0584 (18)	−0.0044 (12)	0.0259 (13)	−0.0030 (13)
C16	0.0475 (12)	0.0561 (14)	0.0650 (19)	−0.0153 (11)	0.0220 (12)	−0.0036 (13)
C2	0.0411 (11)	0.0556 (13)	0.0436 (15)	−0.0127 (10)	0.0138 (10)	−0.0057 (11)
C3	0.0392 (11)	0.0807 (18)	0.0466 (16)	−0.0074 (12)	0.0191 (11)	−0.0078 (13)
C5	0.0490 (13)	0.0467 (12)	0.0576 (17)	−0.0018 (11)	0.0154 (12)	−0.0139 (12)
C4	0.0472 (13)	0.0709 (17)	0.0537 (17)	0.0033 (12)	0.0196 (12)	−0.0178 (13)
O3	0.0489 (8)	0.0299 (7)	0.0510 (11)	−0.0020 (6)	0.0125 (8)	−0.0009 (7)
O4	0.1017 (16)	0.0525 (11)	0.0617 (14)	−0.0037 (10)	0.0148 (12)	−0.0154 (9)
C17	0.0452 (12)	0.0419 (12)	0.0513 (17)	−0.0026 (10)	0.0144 (11)	0.0063 (11)

Zn1—O3	1.9829 (16)	C6—C7	1.444 (3)
Zn1—O1i	2.0204 (16)	N3—C15	1.447 (3)
Zn1—N1	2.0681 (17)	N3—C16	1.449 (3)
Zn1—O1	2.0776 (15)	C10—H10	0.9500
Zn1—O2	2.1104 (15)	C1—C2	1.393 (3)
O1—C1	1.339 (2)	C7—H7	0.9500
O1—Zn1i	2.0204 (16)	C14—H14	0.9500
N2—C8	1.342 (3)	C15—H15A	0.9800
N2—N1	1.384 (2)	C15—H15B	0.9800
N2—H8	0.8800	C15—H15C	0.9800
N1—C7	1.277 (3)	C16—H16A	0.9800
O2—C8	1.250 (2)	C16—H16B	0.9800
C11—C10	1.374 (3)	C16—H16C	0.9800
C11—C12	1.404 (3)	C2—C3	1.378 (3)
C11—H11	0.9500	C2—H2	0.9500
C9—C14	1.387 (3)	C3—C4	1.375 (4)
C9—C10	1.399 (3)	C3—H3	0.9500
C9—C8	1.470 (3)	C5—C4	1.363 (3)
C12—N3	1.364 (3)	C5—H5	0.9500
C12—C13	1.415 (3)	C4—H4	0.9500
C13—C14	1.371 (3)	O3—C17	1.274 (3)
C13—H13	0.9500	O4—C17	1.206 (3)
C6—C5	1.402 (3)	C17—H17	0.9500
C6—C1	1.419 (3)
O3—Zn1—O1i	102.64 (7)	C11—C10—C9	121.2 (2)
O3—Zn1—N1	126.22 (7)	C11—C10—H10	119.4
O1i—Zn1—N1	131.13 (7)	C9—C10—H10	119.4
O3—Zn1—O1	107.34 (6)	O1—C1—C2	120.97 (18)
O1i—Zn1—O1	78.72 (7)	O1—C1—C6	121.88 (18)
N1—Zn1—O1	85.47 (6)	C2—C1—C6	117.1 (2)
O3—Zn1—O2	95.66 (6)	N1—C7—C6	125.24 (19)
O1i—Zn1—O2	102.13 (6)	N1—C7—H7	117.4
N1—Zn1—O2	76.17 (6)	C6—C7—H7	117.4
O1—Zn1—O2	156.30 (6)	C13—C14—C9	122.20 (19)
C1—O1—Zn1i	125.90 (12)	C13—C14—H14	118.9
C1—O1—Zn1	128.65 (12)	C9—C14—H14	118.9
Zn1i—O1—Zn1	101.28 (7)	N3—C15—H15A	109.5
C8—N2—N1	116.42 (16)	N3—C15—H15B	109.5
C8—N2—H8	121.8	H15A—C15—H15B	109.5
N1—N2—H8	121.8	N3—C15—H15C	109.5
C7—N1—N2	117.73 (17)	H15A—C15—H15C	109.5
C7—N1—Zn1	129.16 (14)	H15B—C15—H15C	109.5
N2—N1—Zn1	112.60 (12)	N3—C16—H16A	109.5
C8—O2—Zn1	114.85 (13)	N3—C16—H16B	109.5
C10—C11—C12	121.76 (19)	H16A—C16—H16B	109.5
C10—C11—H11	119.1	N3—C16—H16C	109.5
C12—C11—H11	119.1	H16A—C16—H16C	109.5
C14—C9—C10	117.34 (18)	H16B—C16—H16C	109.5
C14—C9—C8	118.27 (18)	C3—C2—C1	121.7 (2)
C10—C9—C8	124.35 (19)	C3—C2—H2	119.1
N3—C12—C11	122.44 (19)	C1—C2—H2	119.1
N3—C12—C13	121.0 (2)	C4—C3—C2	121.3 (2)
C11—C12—C13	116.57 (18)	C4—C3—H3	119.4
C14—C13—C12	120.9 (2)	C2—C3—H3	119.4
C14—C13—H13	119.5	C4—C5—C6	122.4 (2)
C12—C13—H13	119.5	C4—C5—H5	118.8
O2—C8—N2	119.51 (18)	C6—C5—H5	118.8
O2—C8—C9	120.87 (19)	C5—C4—C3	118.3 (2)
N2—C8—C9	119.62 (17)	C5—C4—H4	120.8
C5—C6—C1	119.1 (2)	C3—C4—H4	120.8
C5—C6—C7	116.03 (19)	C17—O3—Zn1	112.98 (14)
C1—C6—C7	124.82 (19)	O4—C17—O3	125.4 (2)
C12—N3—C15	121.18 (19)	O4—C17—H17	117.3
C12—N3—C16	120.76 (19)	O3—C17—H17	117.3
C15—N3—C16	117.20 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H8···O3ii	0.88	2.00	2.838 (2)	158.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H8⋯O3i	0.88	2.00	2.838 (2)	158

Symmetry code: (i) .