Diaqua­[(E)-2-(2-oxidobenzyl­idene­amino)-2-phenyl­acetato]zinc(II) dimethyl sulfoxide monosolvate

You, J.; Liu, B.; Pang, Y.-J.; Wu, Q.-C.

doi:10.1107/S1600536809020741

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page m734

doi:10.1107/S1600536809020741

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Diaqua[(E)-2-(2-oxidobenzylideneamino)-2-phenylacetato]zinc(II) dimethyl sulfoxide monosolvate

Jun You,^a Bo Liu,^a ^* Yu-Jing Pang ^a and Qing-Cui Wu ^a

^aSchool of Chemistry and Environment Engineering, Harbin University of Science and Technology, Harbin 150040, People's Republic of China
^*Correspondence e-mail: liubo200400@vip.sina.com

(Received 31 May 2009; accepted 1 June 2009; online 6 June 2009)

In the title compound, [Zn(C₁₅H₁₁NO₃)(H₂O)₂]·C₂H₆OS, the Zn(II) ion is coordinated by two O atoms and one N atom of the deprotonated chelate ligand and two water molecules in a distorted trigonal bipyramidal coordination environment. A linear supramolecular structure built from O—H⋯O hydrogen bonds runs parallel to [100].

Related literature

For the synthesis of (E)-2-(2-hydroxybenzylideneamino)-2-phenylacetic acid, see Audriceth et al. (1954 ). For a related zinc complex, see: You et al. (2008 ).

Experimental

Crystal data

[Zn(C₁₅H₁₁NO₃)(H₂O)₂]·C₂H₆OS
M_r = 432.78
Triclinic, $[P \overline 1]$
a = 7.331 (4) Å
b = 9.318 (5) Å
c = 14.578 (9) Å
α = 81.91 (2)°
β = 81.37 (2)°
γ = 80.18 (2)°
V = 963.4 (9) Å³
Z = 2
Mo Kα radiation
μ = 1.42 mm⁻¹
T = 291 K
0.19 × 0.15 × 0.13 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.777, T_max = 0.837
9415 measured reflections
4331 independent reflections
3751 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.098
S = 1.15
4331 reflections
237 parameters
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

N1—Zn1	2.0305 (19)
O1—Zn1	2.1047 (17)
O3—Zn1	1.9742 (18)
O4—Zn1	2.009 (2)
O5—Zn1	2.0015 (19)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H23⋯O6	0.85	1.90	2.725 (3)	164
O4—H24⋯O2ⁱ	0.85	1.88	2.695 (3)	160
O5—H21⋯O2ⁱⁱ	0.85	1.81	2.629 (2)	161
O5—H22⋯O6ⁱⁱⁱ	0.85	1.93	2.742 (3)	159
Symmetry codes: (i) -x+2, -y+1, -z; (ii) x-1, y, z; (iii) -x+1, -y+1, -z.

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ); 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809020741/ng2591sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809020741/ng2591Isup2.hkl

checkCIF report

Comment top

The continuous interest in designing and making novel Schiff base ligand and transition-metal complexes have persisted because of their impressive catalytic property. Recently, our group have reported a Schiff base and Zn(II) complex (You et al., 2008). As the continually working, we report a new title Schiff base complex, herein, synthesized by the reaction of (E)-2-(2-hydroxybenzylideneamino)-2-phenylacetic acid and Zn(OAc)₂.

As shown in Fig. 1, Zn^II ion is five-coordinate in a slightly distorted trigonal-bipyramidal coordination environment, two water molecules and one N formed the equatorial plane and two deprotonated O atoms take up the apices positions.

The cocrystalized dimethylsulfoxide molecules link the discrete coordinate compound to a one-dimensional tubal supramolecular structure, via the O—H···O hydrogen bonds parallel to [100] (Fig. 2).

Related literature top

For the synthesis of (E)-2-(2-hydroxybenzylideneamino)-2-phenylacetic acid, see Audriceth et al. (1954). For a related zinc complex, see: You et al. (2008).

Experimental top

(E)-2-(2-hydroxybenzylideneamino)-2-phenylacetic acid was prepared of 2-amino-2-phenylacetic acid and 2-hydroxybenzaldehyde in aqueous solution (Audriceth et al., 1954). (E)-2-(2-hydroxybenzylideneamino)-2-phenylacetic acid (0.255 g, 1 mmol) and Zn(OAc)₂ (0.190 g, 1 mmol) dissolved in hot aqueous solution (20 ml) then refluxed for 1 huor. After cooling to room temperature the solution was filtered, the residue was recrystaled in DMSO and methanol (10/1, V/V) solution, several days latter, a suitable for X-ray diffraction yellow crystal was obtained.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), showing displacement ellipsoids at the 30% probability level for non-H atoms.
	Fig. 2. A partial packing view, showing the one-dimensional tubal supramolecular structure. H atoms not involved in hydrogen bonds have been omitted for clarity.

Diaqua[(E)-2-(2-oxidobenzylideneamino)-2-phenylacetato]zinc(II) dimethyl sulfoxide solvate top

Crystal data top

[Zn(C₁₅H₁₁NO₃)(H₂O)₂]·C₂H₆OS	Z = 2
M_r = 432.78	F(000) = 448
Triclinic, P1	D_x = 1.492 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.331 (4) Å	Cell parameters from 8052 reflections
b = 9.318 (5) Å	θ = 3.0–27.5°
c = 14.578 (9) Å	µ = 1.42 mm⁻¹
α = 81.91 (2)°	T = 291 K
β = 81.37 (2)°	Block, colorless
γ = 80.18 (2)°	0.19 × 0.15 × 0.13 mm
V = 963.4 (9) Å³

Data collection top

Rigaku R-AXIS RAPID diffractometer	4331 independent reflections
Radiation source: fine-focus sealed tube	3751 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ω scan	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −9→8
T_min = 0.777, T_max = 0.837	k = −12→12
9415 measured reflections	l = −18→18

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.098	H-atom parameters constrained
S = 1.15	w = 1/[σ²(F_o²) + (0.0512P)² + 0.2263P] where P = (F_o² + 2F_c²)/3
4331 reflections	(Δ/σ)_max = 0.001
237 parameters	Δρ_max = 0.48 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

[Zn(C₁₅H₁₁NO₃)(H₂O)₂]·C₂H₆OS	γ = 80.18 (2)°
M_r = 432.78	V = 963.4 (9) Å³
Triclinic, P1	Z = 2
a = 7.331 (4) Å	Mo Kα radiation
b = 9.318 (5) Å	µ = 1.42 mm⁻¹
c = 14.578 (9) Å	T = 291 K
α = 81.91 (2)°	0.19 × 0.15 × 0.13 mm
β = 81.37 (2)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	4331 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3751 reflections with I > 2σ(I)
T_min = 0.777, T_max = 0.837	R_int = 0.024
9415 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.098	H-atom parameters constrained
S = 1.15	Δρ_max = 0.48 e Å⁻³
4331 reflections	Δρ_min = −0.28 e Å⁻³
237 parameters

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
C1	0.9379 (3)	0.7675 (2)	0.26445 (14)	0.0316 (4)
C2	0.7789 (4)	0.8689 (3)	0.24967 (18)	0.0451 (5)
H2	0.6891	0.8462	0.2176	0.054*
C3	0.7553 (5)	1.0041 (3)	0.2831 (2)	0.0589 (7)
H3	0.6491	1.0719	0.2736	0.071*
C4	0.8891 (5)	1.0382 (3)	0.3305 (2)	0.0671 (9)
H4	0.8718	1.1284	0.3535	0.080*
C5	1.0461 (5)	0.9402 (3)	0.3436 (2)	0.0612 (8)
H5	1.1362	0.9643	0.3749	0.073*
C6	1.0726 (4)	0.8041 (3)	0.31051 (17)	0.0457 (6)
H6	1.1806	0.7379	0.3193	0.055*
C7	0.9648 (3)	0.6175 (2)	0.23069 (14)	0.0286 (4)
H7	1.0767	0.5582	0.2531	0.034*
C8	0.9913 (3)	0.6342 (2)	0.12286 (14)	0.0287 (4)
C9	0.7835 (3)	0.4801 (2)	0.34886 (15)	0.0339 (4)
H9	0.8721	0.4896	0.3862	0.041*
C10	0.6363 (3)	0.3983 (2)	0.39195 (15)	0.0356 (5)
C11	0.6505 (4)	0.3309 (3)	0.48364 (17)	0.0521 (6)
H11	0.7511	0.3425	0.5124	0.063*
C12	0.5219 (5)	0.2490 (4)	0.5320 (2)	0.0635 (8)
H12	0.5353	0.2044	0.5923	0.076*
C13	0.3711 (5)	0.2339 (4)	0.4894 (2)	0.0655 (8)
H13	0.2828	0.1781	0.5217	0.079*
C14	0.3488 (4)	0.2995 (3)	0.4004 (2)	0.0559 (7)
H14	0.2444	0.2886	0.3743	0.067*
C15	0.4808 (3)	0.3834 (3)	0.34729 (15)	0.0392 (5)
C16	0.1636 (4)	0.2801 (3)	0.1543 (2)	0.0527 (6)
H16A	0.2255	0.3352	0.1877	0.079*
H16B	0.0506	0.2573	0.1919	0.079*
H16C	0.1341	0.3372	0.0969	0.079*
C17	0.1686 (4)	0.0495 (3)	0.0617 (2)	0.0495 (6)
H17A	0.1290	0.1261	0.0143	0.074*
H17B	0.0612	0.0201	0.1014	0.074*
H17C	0.2381	−0.0330	0.0327	0.074*
N1	0.8040 (2)	0.54080 (19)	0.26458 (12)	0.0301 (4)
O1	0.8636 (2)	0.60996 (18)	0.08213 (10)	0.0366 (3)
O2	1.1404 (2)	0.67381 (19)	0.08264 (11)	0.0400 (4)
O3	0.4514 (2)	0.4435 (2)	0.26298 (12)	0.0505 (4)
O4	0.6986 (3)	0.3510 (2)	0.09429 (13)	0.0581 (5)
H23	0.6190	0.2942	0.0951	0.087*
H24	0.7571	0.3634	0.0395	0.087*
O5	0.4726 (2)	0.7027 (2)	0.11810 (12)	0.0471 (4)
H21	0.3578	0.6969	0.1193	0.071*
H22	0.5174	0.7309	0.0626	0.071*
O6	0.4740 (2)	0.16387 (19)	0.06180 (12)	0.0447 (4)
S1	0.31254 (8)	0.11488 (6)	0.12970 (4)	0.03825 (14)
Zn1	0.63958 (3)	0.52441 (3)	0.167315 (16)	0.03534 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0338 (10)	0.0317 (10)	0.0280 (9)	−0.0083 (8)	0.0023 (8)	−0.0019 (8)
C2	0.0419 (13)	0.0445 (13)	0.0463 (13)	−0.0040 (11)	−0.0015 (10)	−0.0040 (11)
C3	0.0648 (18)	0.0380 (13)	0.0642 (18)	0.0045 (13)	0.0099 (14)	−0.0074 (13)
C4	0.104 (3)	0.0411 (15)	0.0562 (17)	−0.0236 (17)	0.0161 (17)	−0.0183 (13)
C5	0.080 (2)	0.0554 (17)	0.0589 (17)	−0.0311 (16)	−0.0067 (15)	−0.0191 (14)
C6	0.0504 (14)	0.0492 (14)	0.0420 (13)	−0.0155 (12)	−0.0069 (11)	−0.0102 (11)
C7	0.0240 (9)	0.0327 (10)	0.0301 (10)	−0.0082 (8)	−0.0031 (7)	−0.0031 (8)
C8	0.0257 (9)	0.0303 (10)	0.0296 (9)	−0.0069 (8)	0.0021 (7)	−0.0040 (8)
C9	0.0360 (11)	0.0367 (11)	0.0287 (10)	−0.0072 (9)	−0.0026 (8)	−0.0023 (8)
C10	0.0412 (12)	0.0338 (11)	0.0285 (10)	−0.0080 (9)	0.0059 (9)	−0.0009 (8)
C11	0.0544 (15)	0.0632 (16)	0.0338 (12)	−0.0107 (13)	0.0012 (11)	0.0063 (11)
C12	0.070 (2)	0.071 (2)	0.0398 (14)	−0.0145 (16)	0.0081 (13)	0.0177 (13)
C13	0.073 (2)	0.0637 (18)	0.0534 (16)	−0.0298 (16)	0.0221 (15)	0.0079 (14)
C14	0.0502 (15)	0.0702 (18)	0.0470 (14)	−0.0287 (14)	0.0107 (12)	−0.0001 (13)
C15	0.0409 (12)	0.0429 (12)	0.0321 (11)	−0.0141 (10)	0.0088 (9)	−0.0035 (9)
C16	0.0515 (15)	0.0485 (14)	0.0578 (16)	−0.0065 (12)	0.0028 (12)	−0.0166 (12)
C17	0.0400 (13)	0.0417 (13)	0.0701 (17)	−0.0152 (11)	−0.0069 (12)	−0.0076 (12)
N1	0.0288 (8)	0.0341 (9)	0.0271 (8)	−0.0091 (7)	−0.0001 (7)	−0.0014 (7)
O1	0.0290 (7)	0.0560 (10)	0.0274 (7)	−0.0179 (7)	−0.0024 (6)	−0.0014 (7)
O2	0.0281 (7)	0.0587 (10)	0.0355 (8)	−0.0200 (7)	0.0042 (6)	−0.0064 (7)
O3	0.0414 (9)	0.0763 (12)	0.0367 (9)	−0.0303 (9)	−0.0009 (7)	0.0050 (8)
O4	0.0618 (12)	0.0754 (13)	0.0467 (10)	−0.0448 (10)	0.0172 (9)	−0.0239 (9)
O5	0.0268 (8)	0.0655 (11)	0.0470 (9)	−0.0145 (8)	−0.0050 (7)	0.0094 (8)
O6	0.0350 (8)	0.0511 (10)	0.0497 (10)	−0.0179 (7)	0.0021 (7)	−0.0060 (8)
S1	0.0338 (3)	0.0366 (3)	0.0427 (3)	−0.0104 (2)	−0.0032 (2)	0.0048 (2)
Zn1	0.02999 (15)	0.05017 (18)	0.02839 (14)	−0.01813 (11)	−0.00285 (9)	0.00044 (10)

Geometric parameters (Å, º) top

C1—C6	1.386 (3)	C12—H12	0.9300
C1—C2	1.393 (3)	C13—C14	1.376 (4)
C1—C7	1.519 (3)	C13—H13	0.9300
C2—C3	1.388 (4)	C14—C15	1.418 (3)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.383 (5)	C15—O3	1.310 (3)
C3—H3	0.9300	C16—S1	1.777 (3)
C4—C5	1.361 (5)	C16—H16A	0.9600
C4—H4	0.9300	C16—H16B	0.9600
C5—C6	1.393 (4)	C16—H16C	0.9600
C5—H5	0.9300	C17—S1	1.780 (3)
C6—H6	0.9300	C17—H17A	0.9600
C7—N1	1.469 (3)	C17—H17B	0.9600
C7—C8	1.544 (3)	C17—H17C	0.9600
C7—H7	0.9800	N1—Zn1	2.0305 (19)
C8—O1	1.248 (2)	O1—Zn1	2.1047 (17)
C8—O2	1.248 (2)	O3—Zn1	1.9742 (18)
C9—N1	1.276 (3)	O4—Zn1	2.009 (2)
C9—C10	1.443 (3)	O4—H23	0.8500
C9—H9	0.9300	O4—H24	0.8500
C10—C11	1.405 (3)	O5—Zn1	2.0015 (19)
C10—C15	1.430 (3)	O5—H21	0.8500
C11—C12	1.365 (4)	O5—H22	0.8499
C11—H11	0.9300	O6—S1	1.5147 (18)
C12—C13	1.382 (5)

C6—C1—C2	119.6 (2)	C13—C14—C15	121.7 (3)
C6—C1—C7	119.8 (2)	C13—C14—H14	119.2
C2—C1—C7	120.64 (19)	C15—C14—H14	119.2
C3—C2—C1	119.6 (3)	O3—C15—C14	118.8 (2)
C3—C2—H2	120.2	O3—C15—C10	124.8 (2)
C1—C2—H2	120.2	C14—C15—C10	116.4 (2)
C4—C3—C2	120.3 (3)	S1—C16—H16A	109.5
C4—C3—H3	119.9	S1—C16—H16B	109.5
C2—C3—H3	119.9	H16A—C16—H16B	109.5
C5—C4—C3	120.2 (2)	S1—C16—H16C	109.5
C5—C4—H4	119.9	H16A—C16—H16C	109.5
C3—C4—H4	119.9	H16B—C16—H16C	109.5
C4—C5—C6	120.4 (3)	S1—C17—H17A	109.5
C4—C5—H5	119.8	S1—C17—H17B	109.5
C6—C5—H5	119.8	H17A—C17—H17B	109.5
C1—C6—C5	119.9 (3)	S1—C17—H17C	109.5
C1—C6—H6	120.1	H17A—C17—H17C	109.5
C5—C6—H6	120.1	H17B—C17—H17C	109.5
N1—C7—C1	111.97 (16)	C9—N1—C7	119.69 (18)
N1—C7—C8	108.26 (15)	C9—N1—Zn1	124.24 (15)
C1—C7—C8	109.72 (17)	C7—N1—Zn1	115.85 (13)
N1—C7—H7	108.9	C8—O1—Zn1	116.45 (13)
C1—C7—H7	108.9	C15—O3—Zn1	125.28 (15)
C8—C7—H7	108.9	Zn1—O4—H23	121.1
O1—C8—O2	124.70 (19)	Zn1—O4—H24	117.3
O1—C8—C7	118.68 (17)	H23—O4—H24	109.4
O2—C8—C7	116.62 (18)	Zn1—O5—H21	118.0
N1—C9—C10	126.4 (2)	Zn1—O5—H22	108.9
N1—C9—H9	116.8	H21—O5—H22	109.0
C10—C9—H9	116.8	O6—S1—C16	104.74 (13)
C11—C10—C15	119.5 (2)	O6—S1—C17	106.13 (13)
C11—C10—C9	116.5 (2)	C16—S1—C17	98.10 (13)
C15—C10—C9	124.1 (2)	O3—Zn1—O5	97.31 (8)
C12—C11—C10	122.4 (3)	O3—Zn1—O4	96.26 (9)
C12—C11—H11	118.8	O5—Zn1—O4	118.61 (9)
C10—C11—H11	118.8	O3—Zn1—N1	92.18 (8)
C11—C12—C13	118.6 (3)	O5—Zn1—N1	119.53 (8)
C11—C12—H12	120.7	O4—Zn1—N1	119.38 (9)
C13—C12—H12	120.7	O3—Zn1—O1	171.33 (6)
C14—C13—C12	121.5 (3)	O5—Zn1—O1	87.49 (8)
C14—C13—H13	119.3	O4—Zn1—O1	87.69 (7)
C12—C13—H13	119.3	N1—Zn1—O1	79.16 (7)

C6—C1—C2—C3	−1.5 (4)	C11—C10—C15—C14	0.0 (3)
C7—C1—C2—C3	178.5 (2)	C9—C10—C15—C14	−179.7 (2)
C1—C2—C3—C4	0.2 (4)	C10—C9—N1—C7	−178.51 (19)
C2—C3—C4—C5	0.9 (5)	C10—C9—N1—Zn1	−4.2 (3)
C3—C4—C5—C6	−0.8 (5)	C1—C7—N1—C9	−77.4 (2)
C2—C1—C6—C5	1.6 (4)	C8—C7—N1—C9	161.56 (19)
C7—C1—C6—C5	−178.4 (2)	C1—C7—N1—Zn1	107.87 (16)
C4—C5—C6—C1	−0.5 (4)	C8—C7—N1—Zn1	−13.2 (2)
C6—C1—C7—N1	126.6 (2)	O2—C8—O1—Zn1	174.12 (17)
C2—C1—C7—N1	−53.4 (3)	C7—C8—O1—Zn1	−7.0 (2)
C6—C1—C7—C8	−113.2 (2)	C14—C15—O3—Zn1	−165.10 (19)
C2—C1—C7—C8	66.9 (3)	C10—C15—O3—Zn1	16.3 (3)
N1—C7—C8—O1	13.2 (3)	C15—O3—Zn1—O5	−139.4 (2)
C1—C7—C8—O1	−109.3 (2)	C15—O3—Zn1—O4	100.7 (2)
N1—C7—C8—O2	−167.87 (18)	C15—O3—Zn1—N1	−19.2 (2)
C1—C7—C8—O2	69.7 (2)	C9—N1—Zn1—O3	13.31 (19)
N1—C9—C10—C11	174.9 (2)	C7—N1—Zn1—O3	−172.18 (14)
N1—C9—C10—C15	−5.4 (4)	C9—N1—Zn1—O5	112.98 (18)
C15—C10—C11—C12	1.0 (4)	C7—N1—Zn1—O5	−72.52 (15)
C9—C10—C11—C12	−179.3 (3)	C9—N1—Zn1—O4	−85.13 (19)
C10—C11—C12—C13	−0.9 (5)	C7—N1—Zn1—O4	89.38 (15)
C11—C12—C13—C14	−0.2 (5)	C9—N1—Zn1—O1	−166.21 (19)
C12—C13—C14—C15	1.2 (5)	C7—N1—Zn1—O1	8.29 (13)
C13—C14—C15—O3	−179.8 (3)	C8—O1—Zn1—O5	120.12 (16)
C13—C14—C15—C10	−1.1 (4)	C8—O1—Zn1—O4	−121.10 (16)
C11—C10—C15—O3	178.6 (2)	C8—O1—Zn1—N1	−0.59 (15)
C9—C10—C15—O3	−1.1 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H23···O6	0.85	1.90	2.725 (3)	164
O4—H24···O2ⁱ	0.85	1.88	2.695 (3)	160
O5—H21···O2ⁱⁱ	0.85	1.81	2.629 (2)	161
O5—H22···O6ⁱⁱⁱ	0.85	1.93	2.742 (3)	159

Symmetry codes: (i) −x+2, −y+1, −z; (ii) x−1, y, z; (iii) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	[Zn(C₁₅H₁₁NO₃)(H₂O)₂]·C₂H₆OS
M_r	432.78
Crystal system, space group	Triclinic, P1
Temperature (K)	291
a, b, c (Å)	7.331 (4), 9.318 (5), 14.578 (9)
α, β, γ (°)	81.91 (2), 81.37 (2), 80.18 (2)
V (Å³)	963.4 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.42
Crystal size (mm)	0.19 × 0.15 × 0.13

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.777, 0.837
No. of measured, independent and observed [I > 2σ(I)] reflections	9415, 4331, 3751
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.098, 1.15
No. of reflections	4331
No. of parameters	237
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.28

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

N1—Zn1	2.0305 (19)	O4—Zn1	2.009 (2)
O1—Zn1	2.1047 (17)	O5—Zn1	2.0015 (19)
O3—Zn1	1.9742 (18)

C16—S1—C17	98.10 (13)	O4—Zn1—N1	119.38 (9)
O3—Zn1—O5	97.31 (8)	O3—Zn1—O1	171.33 (6)
O3—Zn1—O4	96.26 (9)	O5—Zn1—O1	87.49 (8)
O5—Zn1—O4	118.61 (9)	O4—Zn1—O1	87.69 (7)
O3—Zn1—N1	92.18 (8)	N1—Zn1—O1	79.16 (7)
O5—Zn1—N1	119.53 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H23···O6	0.85	1.90	2.725 (3)	163.8
O4—H24···O2ⁱ	0.85	1.88	2.695 (3)	159.5
O5—H21···O2ⁱⁱ	0.85	1.81	2.629 (2)	161.2
O5—H22···O6ⁱⁱⁱ	0.85	1.93	2.742 (3)	158.5

Symmetry codes: (i) −x+2, −y+1, −z; (ii) x−1, y, z; (iii) −x+1, −y+1, −z.

Acknowledgements

This work was supported by the National Natural Science Foundation of China (grant No. 20272011) and Harbin University of Science and Technology.

References

Audriceth, L. F., Scott, E. S. & Kipper, P. S. (1954). J. Org. Chem. 19, 733–741. Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
You, J., Liu, B., Chen, Y.-Q., Xiao, C. & Zhai, D.-Q. (2008). Acta Cryst. E64, m1338. Web of Science CrossRef IUCr Journals Google Scholar

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Volume 65| Part 7| July 2009| Page m734

doi:10.1107/S1600536809020741

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

Di­aqua­[(E)-2-(2-oxido­benzyl­­idene­amino)-2-phenyl­acetato]zinc(II) di­methyl sulfoxide monosolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Diaqua[(E)-2-(2-oxidobenzylideneamino)-2-phenylacetato]zinc(II) dimethyl sulfoxide monosolvate