Bis[2-(2-hydroxy­ethyl­imino­meth­yl)-6-methoxy­phenolato-κ2N,O1]zinc(II)

Dong, J.-F.; Li, L.-Z.; Yu, W.-J.; Cui, H.; Wang, D.-Q.

doi:10.1107/S1600536807030206

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Bis[2-(2-hydroxyethyliminomethyl)-6-methoxyphenolato-κ²N,O¹]zinc(II)

J.-F. Dong, L.-Z. Li, W.-J. Yu, H. Cui and D.-Q. Wang

In the title complex, [Zn(C₁₀H₁₂NO₃)₂], the Zn^II ion is coordinated by two N,O-bidentate ligands in a distorted tetrahedral geometry. The crystal packing is stabilized by intermolecular O—H

O hydrogen bonds and C—H

Cg interactions (Cg is an aromatic ring centroid). The hydroxy substituent of one ethanolamine group is disordered over two sites with the ratio of refined occupancies being 0.844 (4): 0.156 (4).

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807030206/lh2415sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807030206/lh2415Isup2.hkl Contains datablock I

CCDC reference: 654819

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.011 Å
Disorder in main residue
R factor = 0.078
wR factor = 0.170
Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT601_ALERT_2_B Structure Contains Solvent Accessible VOIDS of .     121.00 A   3 

Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.99
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.52 Ratio
PLAT301_ALERT_3_C Main Residue  Disorder .........................       3.00 Perc.
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         11
PLAT432_ALERT_2_C Short Inter X...Y Contact  C8     ..  O6'     ..       2.98 Ang.

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          6

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

As part of our ongoing studies of Schiff bases, we reported here the synthesis and crystal structure of the title compound (Fig. 1), a new zinc(II) complex with a bidentate Schiff base ligand derived from the condensation of o-vanillin and ethanolamine.

The coordination around zinc is a distored tetrahedral involving two O and N atoms of the ligands. These bond lengths and angles values are similar to the reported values for related structures (Hokelek et al., 2000, Tatar et al., 1999, Dong et al., 2007).

In the crystal structure, the intermolecular hydrogen bonds of O3—H3···O1ⁱ and O3—H3···O2ⁱ(symmetry code: (i) x, y - 1, Z) (Fig. 2) and the relatively short intermolecular distances H18a···Cgⁱⁱ of 2.962Å (symmetry code: 0.5 - x, 1/2 + y, Z; Cg is the centroid of the C12—17 ring) indicating the prescence of weak C—H···π interaction, stabilize the crystal packing along with van der Waals forces.

Related literature top

The bond lengths and angles in the title structure are similar to those in related structures (Hokelek et al., 2000; Tatar et al., 1999; Dong, et al., 2007).

Experimental top

Ethanolamine(1 mmol, 0.059 ml) was dissolved in hot methanol (10 ml) and added in portions to a methanol solution(3 ml) of o-vanillin (1 mmol, 152.14 mg). The mixture was then stirred at 323 K for 2 h. Subsequently, an aqueous solution(2 ml) of zinc acetate dihydrate(1 mmol, 219.5 mg) was added dropwise and stirred for another 5 h. The solution was held at room temperature for ten days, where upon yellow blocks were obtained.

Structure description top

The bond lengths and angles in the title structure are similar to those in related structures (Hokelek et al., 2000; Tatar et al., 1999; Dong, et al., 2007).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. The structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme. Open bonds indicate the minor component of disorder.
	Fig. 2. The packing of the title compound. Hydrogen bond are shown as dashed lines.

Bis[2-(2-hydroxyethyliminomethyl)-6-methoxyphenolato-κ²N²,O¹]zinc(II) top

Crystal data top

[Zn(C₁₀H₁₂NO₃)₂]	F(000) = 1888
M_r = 453.78	D_x = 1.363 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3930 reflections
a = 17.624 (2) Å	θ = 2.3–23.2°
b = 7.2013 (14) Å	µ = 1.15 mm⁻¹
c = 34.853 (3) Å	T = 298 K
V = 4423.3 (11) Å³	Block, yellow
Z = 8	0.59 × 0.26 × 0.24 mm

Data collection top

Bruker SMART CCD diffractometer	3904 independent reflections
Radiation source: fine-focus sealed tube	2485 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.059
φ and ω scans	θ_max = 25.0°, θ_min = 1.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→20
T_min = 0.551, T_max = 0.770	k = −8→6
20138 measured reflections	l = −40→41

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)] = 0.078	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.170	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0382P)² + 21.0111P] where P = (F_o² + 2F_c²)/3
3904 reflections	(Δ/σ)_max = 0.002
266 parameters	Δρ_max = 0.58 e Å⁻³
6 restraints	Δρ_min = −1.04 e Å⁻³

Crystal data top

[Zn(C₁₀H₁₂NO₃)₂]	V = 4423.3 (11) Å³
M_r = 453.78	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 17.624 (2) Å	µ = 1.15 mm⁻¹
b = 7.2013 (14) Å	T = 298 K
c = 34.853 (3) Å	0.59 × 0.26 × 0.24 mm

Data collection top

Bruker SMART CCD diffractometer	3904 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2485 reflections with I > 2σ(I)
T_min = 0.551, T_max = 0.770	R_int = 0.059
20138 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.078	6 restraints
wR(F²) = 0.170	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0382P)² + 21.0111P] where P = (F_o² + 2F_c²)/3
3904 reflections	Δρ_max = 0.58 e Å⁻³
266 parameters	Δρ_min = −1.04 e Å⁻³

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Zn1	0.50272 (4)	0.33878 (10)	0.12373 (2)	0.0460 (3)
N1	0.4934 (3)	0.1249 (6)	0.15934 (15)	0.0429 (13)
N2	0.5700 (3)	0.3369 (8)	0.07788 (17)	0.0514 (14)
O1	0.5436 (3)	0.5126 (6)	0.16004 (13)	0.0561 (13)
O2	0.6315 (3)	0.7510 (7)	0.19242 (18)	0.0809 (19)
O3	0.5677 (3)	−0.1683 (7)	0.11585 (15)	0.0645 (14)
H3	0.5721	−0.2384	0.1343	0.097*
O4	0.4108 (2)	0.3744 (6)	0.09550 (13)	0.0514 (12)
O5	0.2730 (3)	0.3516 (8)	0.07015 (18)	0.0788 (17)
O6	0.6846 (4)	0.0466 (11)	0.0930 (3)	0.112 (3)	0.844 (10)
H6	0.6437	−0.0027	0.0977	0.168*	0.844 (10)
O6'	0.658 (2)	0.109 (5)	0.1366 (9)	0.112 (3)	0.156 (10)
H6'	0.6377	0.0179	0.1272	0.168*	0.156 (10)
C1	0.5196 (3)	0.1339 (10)	0.1936 (2)	0.0490 (18)
H1	0.5110	0.0311	0.2091	0.059*
C2	0.5610 (4)	0.2867 (10)	0.21073 (19)	0.0481 (17)
C3	0.5730 (4)	0.4594 (10)	0.1931 (2)	0.0490 (17)
C4	0.6204 (4)	0.5901 (11)	0.2130 (2)	0.057 (2)
C5	0.6516 (4)	0.5473 (14)	0.2473 (2)	0.069 (2)
H5	0.6826	0.6340	0.2594	0.083*
C6	0.6389 (5)	0.3790 (15)	0.2649 (2)	0.070 (2)
H6A	0.6611	0.3525	0.2885	0.084*
C7	0.5936 (4)	0.2518 (12)	0.2473 (2)	0.058 (2)
H7A	0.5836	0.1396	0.2595	0.070*
C8	0.6948 (5)	0.8650 (12)	0.2030 (3)	0.090 (3)
H8A	0.6881	0.9091	0.2287	0.135*
H8B	0.6981	0.9689	0.1858	0.135*
H8C	0.7407	0.7934	0.2015	0.135*
C9	0.4568 (4)	−0.0470 (9)	0.14736 (19)	0.0507 (18)
H9A	0.4031	−0.0245	0.1432	0.061*
H9B	0.4617	−0.1390	0.1675	0.061*
C10	0.4916 (4)	−0.1202 (8)	0.11123 (18)	0.0482 (18)
H10A	0.4635	−0.2287	0.1029	0.058*
H10B	0.4875	−0.0267	0.0913	0.058*
C11	0.5428 (4)	0.3142 (10)	0.0441 (2)	0.0559 (19)
H11	0.5779	0.3098	0.0241	0.067*
C12	0.4643 (4)	0.2946 (9)	0.03341 (18)	0.0465 (17)
C13	0.4036 (4)	0.3298 (8)	0.05885 (19)	0.0421 (15)
C14	0.3285 (4)	0.3176 (10)	0.0440 (2)	0.0535 (19)
C15	0.3167 (6)	0.2739 (12)	0.0058 (3)	0.077 (3)
H15	0.2674	0.2674	−0.0036	0.093*
C16	0.3767 (6)	0.2399 (13)	−0.0186 (2)	0.082 (3)
H16	0.3677	0.2088	−0.0441	0.099*
C17	0.4493 (5)	0.2520 (12)	−0.0053 (2)	0.074 (2)
H17	0.4895	0.2317	−0.0220	0.088*
C18	0.1962 (4)	0.3283 (14)	0.0591 (3)	0.107 (4)
H18A	0.1813	0.4291	0.0427	0.160*
H18B	0.1647	0.3269	0.0815	0.160*
H18C	0.1907	0.2130	0.0455	0.160*
C19	0.6518 (3)	0.3659 (11)	0.0824 (2)	0.068 (2)
H19A	0.6609	0.4877	0.0933	0.081*
H19B	0.6761	0.3613	0.0574	0.081*
C20	0.6857 (5)	0.2195 (11)	0.1080 (3)	0.091 (3)
H20A	0.7378	0.2531	0.1137	0.109*	0.844 (10)
H20B	0.6580	0.2184	0.1321	0.109*	0.844 (10)
H20C	0.7024	0.1211	0.0910	0.109*	0.156 (10)
H20D	0.7317	0.2751	0.1181	0.109*	0.156 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0508 (4)	0.0403 (4)	0.0471 (4)	−0.0061 (4)	−0.0087 (4)	0.0018 (4)
N1	0.045 (3)	0.031 (3)	0.053 (3)	−0.009 (3)	0.007 (3)	0.000 (2)
N2	0.041 (3)	0.053 (4)	0.060 (4)	−0.009 (3)	0.003 (3)	0.011 (3)
O1	0.071 (3)	0.034 (3)	0.063 (3)	0.000 (2)	−0.025 (3)	−0.002 (2)
O2	0.083 (4)	0.048 (3)	0.112 (5)	−0.007 (3)	−0.060 (4)	−0.005 (3)
O3	0.062 (3)	0.052 (3)	0.079 (4)	−0.002 (3)	0.010 (3)	0.002 (3)
O4	0.043 (3)	0.059 (3)	0.052 (3)	0.002 (2)	−0.001 (2)	−0.006 (2)
O5	0.038 (3)	0.085 (4)	0.113 (5)	−0.004 (3)	−0.009 (3)	−0.003 (4)
O6	0.056 (4)	0.081 (6)	0.200 (10)	0.003 (4)	0.010 (5)	−0.025 (6)
O6'	0.056 (4)	0.081 (6)	0.200 (10)	0.003 (4)	0.010 (5)	−0.025 (6)
C1	0.043 (4)	0.049 (4)	0.056 (4)	0.005 (3)	0.010 (3)	0.007 (4)
C2	0.041 (4)	0.058 (5)	0.046 (4)	0.005 (3)	0.006 (3)	0.001 (4)
C3	0.047 (4)	0.050 (4)	0.050 (4)	0.013 (3)	−0.009 (3)	−0.014 (4)
C4	0.049 (4)	0.067 (5)	0.055 (5)	0.015 (4)	−0.013 (4)	−0.022 (4)
C5	0.050 (5)	0.100 (7)	0.056 (5)	0.015 (5)	−0.014 (4)	−0.037 (5)
C6	0.057 (5)	0.108 (8)	0.045 (4)	0.014 (5)	−0.002 (4)	−0.013 (5)
C7	0.055 (4)	0.081 (6)	0.038 (4)	0.009 (4)	0.009 (4)	0.007 (4)
C8	0.077 (6)	0.054 (5)	0.139 (9)	−0.013 (5)	−0.042 (6)	−0.015 (6)
C9	0.051 (4)	0.036 (4)	0.065 (5)	−0.010 (3)	0.006 (4)	0.001 (4)
C10	0.073 (5)	0.026 (3)	0.046 (4)	−0.009 (3)	−0.009 (4)	−0.008 (3)
C11	0.055 (5)	0.057 (5)	0.056 (5)	0.007 (4)	0.018 (4)	0.009 (4)
C12	0.059 (4)	0.044 (4)	0.037 (4)	−0.003 (3)	0.001 (3)	0.002 (3)
C13	0.049 (4)	0.029 (3)	0.049 (4)	−0.007 (3)	−0.008 (3)	−0.001 (3)
C14	0.051 (4)	0.038 (4)	0.072 (5)	−0.004 (4)	−0.020 (4)	0.003 (4)
C15	0.090 (7)	0.069 (6)	0.073 (6)	−0.011 (5)	−0.044 (5)	0.000 (5)
C16	0.119 (8)	0.084 (7)	0.044 (5)	−0.015 (6)	−0.025 (5)	−0.009 (5)
C17	0.090 (6)	0.085 (7)	0.046 (5)	−0.007 (5)	0.004 (5)	−0.002 (4)
C18	0.040 (5)	0.090 (7)	0.189 (11)	−0.007 (5)	−0.026 (6)	0.020 (8)
C19	0.042 (4)	0.063 (5)	0.098 (6)	−0.007 (4)	0.009 (4)	0.018 (5)
C20	0.044 (5)	0.070 (6)	0.157 (10)	0.006 (4)	−0.031 (6)	−0.003 (7)

Geometric parameters (Å, º) top

Zn1—O4	1.913 (4)	C7—H7A	0.9300
Zn1—O1	1.921 (4)	C8—H8A	0.9600
Zn1—N1	1.985 (5)	C8—H8B	0.9600
Zn1—N2	1.990 (6)	C8—H8C	0.9600
N1—C1	1.281 (8)	C9—C10	1.497 (8)
N1—C9	1.458 (7)	C9—H9A	0.9700
N2—C11	1.283 (9)	C9—H9B	0.9700
N2—C19	1.465 (7)	C10—H10A	0.9700
O1—C3	1.319 (8)	C10—H10B	0.9700
O2—C4	1.378 (9)	C11—C12	1.440 (10)
O2—C8	1.433 (8)	C11—H11	0.9300
O3—C10	1.394 (7)	C12—C17	1.408 (10)
O3—H3	0.8200	C12—C13	1.412 (9)
O4—C13	1.323 (7)	C13—C14	1.425 (9)
O5—C14	1.358 (9)	C14—C15	1.383 (11)
O5—C18	1.417 (8)	C15—C16	1.379 (12)
O6—C20	1.352 (8)	C15—H15	0.9300
O6—H6	0.8200	C16—C17	1.362 (12)
O6—H20C	0.6256	C16—H16	0.9300
O6'—C20	1.361 (11)	C17—H17	0.9300
O6'—H6'	0.8200	C18—H18A	0.9600
C1—C2	1.450 (10)	C18—H18B	0.9600
C1—H1	0.9300	C18—H18C	0.9600
C2—C3	1.404 (10)	C19—C20	1.506 (9)
C2—C7	1.421 (9)	C19—H19A	0.9700
C3—C4	1.437 (9)	C19—H19B	0.9700
C4—C5	1.351 (10)	C20—H20A	0.9700
C5—C6	1.376 (11)	C20—H20B	0.9700
C5—H5	0.9300	C20—H20C	0.9700
C6—C7	1.362 (11)	C20—H20D	0.9700
C6—H6A	0.9300

O4—Zn1—O1	124.7 (2)	C9—C10—H10A	109.1
O4—Zn1—N1	110.8 (2)	O3—C10—H10B	109.1
O1—Zn1—N1	97.2 (2)	C9—C10—H10B	109.1
O4—Zn1—N2	95.3 (2)	H10A—C10—H10B	107.8
O1—Zn1—N2	108.1 (2)	N2—C11—C12	127.4 (6)
N1—Zn1—N2	123.1 (2)	N2—C11—H11	116.3
C1—N1—C9	118.0 (6)	C12—C11—H11	116.3
C1—N1—Zn1	120.9 (4)	C17—C12—C13	119.9 (7)
C9—N1—Zn1	121.1 (4)	C17—C12—C11	116.7 (7)
C11—N2—C19	118.9 (6)	C13—C12—C11	123.3 (6)
C11—N2—Zn1	121.1 (5)	O4—C13—C12	125.3 (6)
C19—N2—Zn1	120.0 (5)	O4—C13—C14	117.0 (6)
C3—O1—Zn1	122.2 (4)	C12—C13—C14	117.7 (6)
C4—O2—C8	117.4 (6)	O5—C14—C15	125.3 (7)
C10—O3—H3	109.5	O5—C14—C13	114.5 (6)
C13—O4—Zn1	123.0 (4)	C15—C14—C13	120.2 (8)
C14—O5—C18	118.9 (7)	C16—C15—C14	121.3 (8)
C20—O6—H6	109.5	C16—C15—H15	119.4
H6—O6—H20C	146.5	C14—C15—H15	119.4
C20—O6'—H6'	109.5	C17—C16—C15	119.9 (8)
N1—C1—C2	127.2 (6)	C17—C16—H16	120.1
N1—C1—H1	116.4	C15—C16—H16	120.1
C2—C1—H1	116.4	C16—C17—C12	121.1 (8)
C3—C2—C7	119.3 (7)	C16—C17—H17	119.4
C3—C2—C1	124.6 (6)	C12—C17—H17	119.4
C7—C2—C1	116.1 (7)	O5—C18—H18A	109.5
O1—C3—C2	125.5 (6)	O5—C18—H18B	109.5
O1—C3—C4	117.4 (7)	H18A—C18—H18B	109.5
C2—C3—C4	117.1 (7)	O5—C18—H18C	109.5
C5—C4—O2	126.5 (8)	H18A—C18—H18C	109.5
C5—C4—C3	121.0 (8)	H18B—C18—H18C	109.5
O2—C4—C3	112.4 (6)	N2—C19—C20	110.7 (6)
C4—C5—C6	121.9 (8)	N2—C19—H19A	109.5
C4—C5—H5	119.1	C20—C19—H19A	109.5
C6—C5—H5	119.1	N2—C19—H19B	109.5
C7—C6—C5	119.2 (8)	C20—C19—H19B	109.5
C7—C6—H6A	120.4	H19A—C19—H19B	108.1
C5—C6—H6A	120.4	O6—C20—O6'	75.0 (19)
C6—C7—C2	121.5 (8)	O6—C20—C19	114.2 (9)
C6—C7—H7A	119.3	O6'—C20—C19	134.6 (18)
C2—C7—H7A	119.3	O6—C20—H20A	108.7
O2—C8—H8A	109.5	O6'—C20—H20A	109.4
O2—C8—H8B	109.5	C19—C20—H20A	108.7
H8A—C8—H8B	109.5	O6—C20—H20B	108.7
O2—C8—H8C	109.5	C19—C20—H20B	108.7
H8A—C8—H8C	109.5	H20A—C20—H20B	107.6
H8B—C8—H8C	109.5	O6'—C20—H20C	97.4
N1—C9—C10	111.0 (5)	C19—C20—H20C	105.6
N1—C9—H9A	109.4	H20A—C20—H20C	91.0
C10—C9—H9A	109.4	H20B—C20—H20C	132.5
N1—C9—H9B	109.4	O6—C20—H20D	122.1
C10—C9—H9B	109.4	O6'—C20—H20D	105.8
H9A—C9—H9B	108.0	C19—C20—H20D	104.9
O3—C10—C9	112.7 (5)	H20B—C20—H20D	96.3
O3—C10—H10A	109.1	H20C—C20—H20D	105.5

O4—Zn1—N1—C1	−137.9 (5)	C3—C4—C5—C6	−0.9 (11)
O1—Zn1—N1—C1	−6.4 (5)	C4—C5—C6—C7	0.0 (12)
N2—Zn1—N1—C1	110.7 (5)	C5—C6—C7—C2	2.0 (11)
O4—Zn1—N1—C9	42.2 (5)	C3—C2—C7—C6	−3.0 (10)
O1—Zn1—N1—C9	173.7 (5)	C1—C2—C7—C6	174.5 (6)
N2—Zn1—N1—C9	−69.3 (5)	C1—N1—C9—C10	−126.1 (6)
O4—Zn1—N2—C11	−16.0 (6)	Zn1—N1—C9—C10	53.9 (7)
O1—Zn1—N2—C11	−145.2 (6)	N1—C9—C10—O3	63.3 (7)
N1—Zn1—N2—C11	103.1 (6)	C19—N2—C11—C12	−176.1 (7)
O4—Zn1—N2—C19	162.6 (5)	Zn1—N2—C11—C12	2.5 (11)
O1—Zn1—N2—C19	33.4 (6)	N2—C11—C12—C17	−173.6 (8)
N1—Zn1—N2—C19	−78.3 (6)	N2—C11—C12—C13	11.3 (12)
O4—Zn1—O1—C3	138.0 (5)	Zn1—O4—C13—C12	−16.3 (9)
N1—Zn1—O1—C3	16.4 (5)	Zn1—O4—C13—C14	164.1 (4)
N2—Zn1—O1—C3	−111.9 (5)	C17—C12—C13—O4	−178.7 (7)
O1—Zn1—O4—C13	139.0 (5)	C11—C12—C13—O4	−3.8 (11)
N1—Zn1—O4—C13	−105.8 (5)	C17—C12—C13—C14	0.9 (10)
N2—Zn1—O4—C13	22.6 (5)	C11—C12—C13—C14	175.8 (7)
C9—N1—C1—C2	176.8 (6)	C18—O5—C14—C15	5.0 (12)
Zn1—N1—C1—C2	−3.1 (9)	C18—O5—C14—C13	−174.9 (7)
N1—C1—C2—C3	6.4 (11)	O4—C13—C14—O5	−0.9 (9)
N1—C1—C2—C7	−171.1 (6)	C12—C13—C14—O5	179.5 (6)
Zn1—O1—C3—C2	−18.0 (9)	O4—C13—C14—C15	179.2 (7)
Zn1—O1—C3—C4	163.0 (5)	C12—C13—C14—C15	−0.5 (10)
C7—C2—C3—O1	−177.0 (6)	O5—C14—C15—C16	−179.4 (8)
C1—C2—C3—O1	5.6 (11)	C13—C14—C15—C16	0.5 (12)
C7—C2—C3—C4	2.0 (9)	C14—C15—C16—C17	−1.0 (14)
C1—C2—C3—C4	−175.3 (6)	C15—C16—C17—C12	1.5 (14)
C8—O2—C4—C5	15.9 (11)	C13—C12—C17—C16	−1.4 (12)
C8—O2—C4—C3	−161.0 (7)	C11—C12—C17—C16	−176.7 (8)
O1—C3—C4—C5	179.0 (6)	C11—N2—C19—C20	−122.0 (8)
C2—C3—C4—C5	−0.1 (10)	Zn1—N2—C19—C20	59.4 (9)
O1—C3—C4—O2	−4.0 (9)	N2—C19—C20—O6	67.2 (11)
C2—C3—C4—O2	176.9 (6)	N2—C19—C20—O6'	−25 (3)
O2—C4—C5—C6	−177.5 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1ⁱ	0.82	2.07	2.799 (7)	148
O3—H3···O2ⁱ	0.82	2.28	2.954 (8)	139

Symmetry code: (i) x, y−1, z.

Experimental details

Crystal data
Chemical formula	[Zn(C₁₀H₁₂NO₃)₂]
M_r	453.78
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	298
a, b, c (Å)	17.624 (2), 7.2013 (14), 34.853 (3)
V (Å³)	4423.3 (11)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.15
Crystal size (mm)	0.59 × 0.26 × 0.24

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.551, 0.770
No. of measured, independent and observed [I > 2σ(I)] reflections	20138, 3904, 2485
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.078, 0.170, 1.08
No. of reflections	3904
No. of parameters	266
No. of restraints	6
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.0382P)² + 21.0111P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	0.58, −1.04

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL.

Selected geometric parameters (Å, º) top

Zn1—O4	1.913 (4)	Zn1—N1	1.985 (5)
Zn1—O1	1.921 (4)	Zn1—N2	1.990 (6)

O4—Zn1—O1	124.7 (2)	O4—Zn1—N2	95.3 (2)
O4—Zn1—N1	110.8 (2)	O1—Zn1—N2	108.1 (2)
O1—Zn1—N1	97.2 (2)	N1—Zn1—N2	123.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1ⁱ	0.82	2.07	2.799 (7)	148.3
O3—H3···O2ⁱ	0.82	2.28	2.954 (8)	139.3

Symmetry code: (i) x, y−1, z.

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