catena-Poly[[(dimethyl sulfoxide-κO)zinc(II)]-μ-(E)-2-[(2-oxido-1-naphth­yl)­methyl­eneamino]propanoato-κ4O2,N,O1:O1′]

You, J.; Liu, B.; Chen, Y.-Q.; Xiao, C.; Zhai, D.-Q.

doi:10.1107/S1600536808030614

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page m1338

doi:10.1107/S1600536808030614

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catena-Poly[[(dimethyl sulfoxide-κO)zinc(II)]-μ-(E)-2-[(2-oxido-1-naphthyl)methyleneamino]propanoato-κ⁴O²,N,O¹:O^1′]

Jun You,^a Bo Liu,^a ^* Yan-Qiong Chen,^a Cui Xiao ^a and Duo-Qi Zhai ^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 22 September 2008; accepted 23 September 2008; online 27 September 2008)

In the title coordination polymer, [Zn(C₁₄H₁₁NO₃)(C₂H₆OS)]_n, each Zn^II ion is five-coordinated in a slightly distorted trigonal–bipyramidal coordination environment, formed by three O atoms from two 2-[(2-oxido-1-naphthyl)methyleneamino]propanoate ligands, one O atom from a dimethyl sulfoxide molecule and the N atom from the aminopropanoate ligand. The propanoate ligands bridge Zn^II ions, forming a zigzag chain parallel to [010].

Related literature

For the synthesis of (E)-2-[(2-hydroxynaphthalen-1-yl)methyleneamino]propanoic acid, see: Audriceth et al. (1954 ).

Experimental

Crystal data

[Zn(C₁₄H₁₁NO₃)(C₂H₆OS)]
M_r = 384.74
Monoclinic, P 2₁
a = 9.676 (4) Å
b = 7.651 (4) Å
c = 11.715 (5) Å
β = 106.256 (15)°
V = 832.6 (7) Å³
Z = 2
Mo Kα radiation
μ = 1.62 mm⁻¹
T = 291 (2) K
0.31 × 0.28 × 0.24 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.633, T_max = 0.697
8191 measured reflections
3729 independent reflections
3533 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.024
wR(F²) = 0.056
S = 1.06
3729 reflections
211 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.19 e Å⁻³
Absolute structure: Flack (1983 ), 1675 Friedel pairs
Flack parameter: 0.006 (8)

Table 1
Selected geometric parameters (Å, °)

N1—Zn1	2.0119 (18)
O1—Zn1	2.0040 (15)
O2—Zn1	2.1891 (16)
O3—Zn1ⁱ	1.9560 (15)
O4—Zn1	2.0520 (17)

O3ⁱⁱ—Zn1—O1	98.54 (7)
O3ⁱⁱ—Zn1—N1	138.57 (7)
O1—Zn1—N1	88.32 (7)
O3ⁱⁱ—Zn1—O4	101.12 (7)
O1—Zn1—O4	96.09 (7)
N1—Zn1—O4	118.82 (7)
O3ⁱⁱ—Zn1—O2	93.89 (7)
O1—Zn1—O2	166.10 (6)
N1—Zn1—O2	78.22 (6)
O4—Zn1—O2	87.52 (7)
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+1]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+1]$ .

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 I, global. DOI: 10.1107/S1600536808030614/ng2495sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808030614/ng2495Isup2.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. In this paper, we report the new title compound, (I), synthesized by the reaction of (E)-2-((2-hydroxynaphthalen-1-yl)methyleneamino)propanoic acid ligands and Zn(OAc)₂ in an aqueous solution.

As shown in Fig. 1, Zn^II ion is five-coordinate in a slightly distorted trigonal-bipyramidal coordination environment, formed by four O atoms and one N atom. Each quadridentate Schiff base ligand bridge two different Cu^II ions, resulting in a one-dimensional polymeric structure chain (Fig. 2).

Related literature top

For the synthesis of (E)-2-[(2-hydroxynaphthalen-1-yl)methyleneamino]propanoic acid see Audriceth et al., (1954).

Experimental top

(E)-2-((2-Hydroxynaphthalen-1-yl)methyleneamino)propanoic acid was prepared of L-alanine acid and 2-hydroxy-1-naphthaldehyde in aqueous solution (Audriceth et al., 1954). (E)-2-((2-Hydroxynaphthalen-1-yl)methyleneamino)propanoic acid (0.243 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. [Symmetry code: (I) -x + 1, 1/2 + y, -z + 1].
	Fig. 2. A partial packing view, showing the one-dimensional chain structure. H atoms have been omitted for clarity.

catena-Poly[[(dimethyl sulfoxide-κO)zinc(II)]- µ-(E)-2-[(2-oxido-1-naphthyl)methyleneamino]propanoato-κ⁴O²,N,O¹:O^1'] top

Crystal data top

[Zn(C₁₄H₁₁NO₃)(C₂H₆OS)]	F(000) = 396
M_r = 384.74	D_x = 1.535 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 7870 reflections
a = 9.676 (4) Å	θ = 3.2–27.5°
b = 7.651 (4) Å	µ = 1.62 mm⁻¹
c = 11.715 (5) Å	T = 291 K
β = 106.256 (15)°	Block, yellow
V = 832.6 (7) Å³	0.31 × 0.28 × 0.24 mm
Z = 2

Data collection top

Rigaku R-AXIS RAPID diffractometer	3729 independent reflections
Radiation source: fine-focus sealed tube	3533 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ω scans	θ_max = 27.5°, θ_min = 3.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −11→12
T_min = 0.633, T_max = 0.697	k = −9→9
8191 measured reflections	l = −15→15

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.024	H-atom parameters constrained
wR(F²) = 0.056	w = 1/[σ²(F_o²) + (0.0259P)²] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
3729 reflections	Δρ_max = 0.25 e Å⁻³
211 parameters	Δρ_min = −0.19 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1675 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.006 (8)

Crystal data top

[Zn(C₁₄H₁₁NO₃)(C₂H₆OS)]	V = 832.6 (7) Å³
M_r = 384.74	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 9.676 (4) Å	µ = 1.62 mm⁻¹
b = 7.651 (4) Å	T = 291 K
c = 11.715 (5) Å	0.31 × 0.28 × 0.24 mm
β = 106.256 (15)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	3729 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3533 reflections with I > 2σ(I)
T_min = 0.633, T_max = 0.697	R_int = 0.020
8191 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	H-atom parameters constrained
wR(F²) = 0.056	Δρ_max = 0.25 e Å⁻³
S = 1.06	Δρ_min = −0.19 e Å⁻³
3729 reflections	Absolute structure: Flack (1983), 1675 Friedel pairs
211 parameters	Absolute structure parameter: 0.006 (8)
1 restraint

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	0.7743 (2)	−0.1178 (3)	0.23967 (18)	0.0288 (4)
C2	0.66925 (19)	−0.0224 (3)	0.15494 (15)	0.0272 (4)
C3	0.6855 (2)	0.0055 (4)	0.03564 (15)	0.0304 (4)
C4	0.5858 (3)	0.0965 (3)	−0.0557 (2)	0.0429 (6)
H4	0.5020	0.1392	−0.0416	0.051*
C5	0.6085 (3)	0.1243 (4)	−0.1655 (2)	0.0477 (6)
H5	0.5400	0.1837	−0.2243	0.057*
C6	0.7336 (3)	0.0636 (3)	−0.1883 (2)	0.0483 (6)
H6	0.7504	0.0859	−0.2613	0.058*
C7	0.8305 (3)	−0.0276 (4)	−0.10433 (19)	0.0445 (6)
H7	0.9131	−0.0694	−0.1209	0.053*
C8	0.8094 (2)	−0.0613 (3)	0.00897 (19)	0.0340 (5)
C9	0.9098 (2)	−0.1605 (4)	0.0950 (2)	0.0418 (5)
H9	0.9890	−0.2075	0.0756	0.050*
C10	0.8947 (2)	−0.1897 (3)	0.2055 (2)	0.0382 (5)
H10	0.9628	−0.2568	0.2595	0.046*
C11	0.5465 (2)	0.0524 (3)	0.18248 (18)	0.0292 (4)
H11	0.4778	0.1043	0.1198	0.035*
C12	0.3897 (2)	0.1430 (3)	0.29272 (17)	0.0307 (4)
H12	0.3676	0.2387	0.2349	0.037*
C13	0.2635 (2)	0.0163 (5)	0.2663 (3)	0.0612 (9)
H13A	0.2422	−0.0219	0.1851	0.092*
H13B	0.1808	0.0738	0.2788	0.092*
H13C	0.2879	−0.0829	0.3182	0.092*
C14	0.4141 (2)	0.2180 (3)	0.41799 (18)	0.0274 (4)
C15	0.7228 (3)	0.4372 (3)	0.3802 (3)	0.0555 (7)
H15A	0.6852	0.3618	0.3132	0.083*
H15B	0.7508	0.5467	0.3534	0.083*
H15C	0.6501	0.4571	0.4202	0.083*
C16	0.9720 (3)	0.2924 (4)	0.3760 (3)	0.0566 (7)
H16A	1.0605	0.2349	0.4161	0.085*
H16B	0.9930	0.3998	0.3418	0.085*
H16C	0.9161	0.2180	0.3143	0.085*
N1	0.52124 (17)	0.0554 (2)	0.28544 (14)	0.0268 (3)
O1	0.77231 (16)	−0.1464 (2)	0.34856 (12)	0.0355 (3)
O2	0.51906 (16)	0.1680 (2)	0.49919 (13)	0.0372 (4)
O3	0.32074 (15)	0.3268 (2)	0.42825 (13)	0.0354 (3)
O4	0.82733 (16)	0.1620 (2)	0.51567 (15)	0.0422 (4)
S1	0.87374 (6)	0.33792 (8)	0.47907 (5)	0.03915 (13)
Zn1	0.66361 (2)	−0.00892 (3)	0.440772 (16)	0.02749 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0313 (10)	0.0256 (11)	0.0325 (9)	−0.0010 (8)	0.0141 (9)	−0.0017 (8)
C2	0.0308 (8)	0.0236 (10)	0.0288 (8)	0.0005 (10)	0.0113 (7)	−0.0007 (10)
C3	0.0376 (9)	0.0261 (11)	0.0303 (8)	−0.0042 (11)	0.0141 (8)	−0.0031 (10)
C4	0.0557 (15)	0.0403 (14)	0.0372 (11)	0.0075 (12)	0.0204 (12)	0.0064 (10)
C5	0.0727 (17)	0.0373 (14)	0.0331 (11)	−0.0006 (13)	0.0146 (12)	0.0055 (10)
C6	0.0787 (18)	0.0388 (13)	0.0374 (11)	−0.0155 (13)	0.0323 (14)	−0.0064 (10)
C7	0.0566 (13)	0.0462 (16)	0.0411 (10)	−0.0114 (14)	0.0308 (11)	−0.0094 (12)
C8	0.0387 (11)	0.0339 (13)	0.0330 (10)	−0.0073 (9)	0.0162 (9)	−0.0070 (8)
C9	0.0357 (11)	0.0521 (15)	0.0441 (12)	0.0053 (11)	0.0221 (11)	−0.0068 (11)
C10	0.0345 (11)	0.0424 (14)	0.0392 (11)	0.0104 (10)	0.0130 (10)	−0.0003 (10)
C11	0.0311 (10)	0.0269 (10)	0.0291 (9)	0.0025 (8)	0.0076 (9)	0.0001 (7)
C12	0.0280 (10)	0.0330 (12)	0.0319 (10)	0.0043 (9)	0.0096 (9)	−0.0071 (9)
C13	0.0308 (11)	0.073 (2)	0.0840 (18)	−0.0102 (14)	0.0225 (12)	−0.0487 (19)
C14	0.0279 (10)	0.0267 (10)	0.0333 (10)	−0.0044 (8)	0.0181 (9)	−0.0043 (8)
C15	0.0493 (14)	0.0333 (14)	0.088 (2)	0.0012 (11)	0.0255 (15)	0.0115 (12)
C16	0.0464 (15)	0.0558 (19)	0.0764 (19)	−0.0036 (13)	0.0319 (15)	−0.0019 (15)
N1	0.0266 (8)	0.0274 (9)	0.0284 (7)	0.0022 (6)	0.0106 (7)	−0.0035 (6)
O1	0.0414 (8)	0.0361 (9)	0.0325 (7)	0.0111 (7)	0.0161 (7)	0.0074 (6)
O2	0.0369 (8)	0.0455 (10)	0.0309 (7)	0.0056 (7)	0.0121 (7)	−0.0044 (7)
O3	0.0358 (8)	0.0372 (9)	0.0365 (7)	0.0056 (7)	0.0156 (7)	−0.0104 (7)
O4	0.0371 (8)	0.0357 (9)	0.0520 (9)	−0.0084 (7)	0.0094 (7)	0.0051 (8)
S1	0.0388 (3)	0.0311 (3)	0.0503 (3)	−0.0096 (2)	0.0169 (3)	−0.0059 (2)
Zn1	0.02884 (11)	0.02883 (11)	0.02707 (10)	0.00032 (12)	0.01157 (8)	0.00374 (11)

Geometric parameters (Å, º) top

C1—O1	1.300 (2)	C12—C14	1.531 (3)
C1—C2	1.410 (3)	C12—H12	0.9800
C1—C10	1.443 (3)	C13—H13A	0.9600
C2—C11	1.434 (3)	C13—H13B	0.9600
C2—C3	1.465 (2)	C13—H13C	0.9600
C3—C4	1.408 (3)	C14—O2	1.242 (3)
C3—C8	1.416 (3)	C14—O3	1.259 (3)
C4—C5	1.381 (3)	C15—S1	1.762 (3)
C4—H4	0.9300	C15—H15A	0.9600
C5—C6	1.391 (4)	C15—H15B	0.9600
C5—H5	0.9300	C15—H15C	0.9600
C6—C7	1.348 (4)	C16—S1	1.768 (3)
C6—H6	0.9300	C16—H16A	0.9600
C7—C8	1.422 (3)	C16—H16B	0.9600
C7—H7	0.9300	C16—H16C	0.9600
C8—C9	1.409 (3)	N1—Zn1	2.0119 (18)
C9—C10	1.361 (3)	O1—Zn1	2.0040 (15)
C9—H9	0.9300	O2—Zn1	2.1891 (16)
C10—H10	0.9300	O3—Zn1ⁱ	1.9560 (15)
C11—N1	1.296 (2)	O4—S1	1.5184 (18)
C11—H11	0.9300	O4—Zn1	2.0520 (17)
C12—N1	1.462 (2)	Zn1—O3ⁱⁱ	1.9560 (15)
C12—C13	1.521 (3)

O1—C1—C2	124.91 (17)	C12—C13—H13B	109.5
O1—C1—C10	116.32 (19)	H13A—C13—H13B	109.5
C2—C1—C10	118.77 (17)	C12—C13—H13C	109.5
C1—C2—C11	121.86 (16)	H13A—C13—H13C	109.5
C1—C2—C3	119.89 (17)	H13B—C13—H13C	109.5
C11—C2—C3	118.24 (18)	O2—C14—O3	125.85 (18)
C4—C3—C8	116.96 (17)	O2—C14—C12	119.49 (17)
C4—C3—C2	124.27 (18)	O3—C14—C12	114.66 (19)
C8—C3—C2	118.77 (19)	S1—C15—H15A	109.5
C5—C4—C3	122.0 (2)	S1—C15—H15B	109.5
C5—C4—H4	119.0	H15A—C15—H15B	109.5
C3—C4—H4	119.0	S1—C15—H15C	109.5
C4—C5—C6	120.1 (2)	H15A—C15—H15C	109.5
C4—C5—H5	120.0	H15B—C15—H15C	109.5
C6—C5—H5	120.0	S1—C16—H16A	109.5
C7—C6—C5	119.9 (2)	S1—C16—H16B	109.5
C7—C6—H6	120.1	H16A—C16—H16B	109.5
C5—C6—H6	120.1	S1—C16—H16C	109.5
C6—C7—C8	121.5 (2)	H16A—C16—H16C	109.5
C6—C7—H7	119.2	H16B—C16—H16C	109.5
C8—C7—H7	119.2	C11—N1—C12	117.15 (17)
C9—C8—C3	119.56 (17)	C11—N1—Zn1	125.29 (13)
C9—C8—C7	120.97 (19)	C12—N1—Zn1	116.50 (12)
C3—C8—C7	119.5 (2)	C1—O1—Zn1	126.51 (14)
C10—C9—C8	122.14 (19)	C14—O2—Zn1	114.09 (12)
C10—C9—H9	118.9	C14—O3—Zn1ⁱ	126.85 (14)
C8—C9—H9	118.9	S1—O4—Zn1	134.27 (11)
C9—C10—C1	120.8 (2)	O4—S1—C15	108.15 (11)
C9—C10—H10	119.6	O4—S1—C16	106.05 (12)
C1—C10—H10	119.6	C15—S1—C16	98.14 (15)
N1—C11—C2	126.87 (19)	O3ⁱⁱ—Zn1—O1	98.54 (7)
N1—C11—H11	116.6	O3ⁱⁱ—Zn1—N1	138.57 (7)
C2—C11—H11	116.6	O1—Zn1—N1	88.32 (7)
N1—C12—C13	111.01 (19)	O3ⁱⁱ—Zn1—O4	101.12 (7)
N1—C12—C14	108.94 (16)	O1—Zn1—O4	96.09 (7)
C13—C12—C14	109.48 (17)	N1—Zn1—O4	118.82 (7)
N1—C12—H12	109.1	O3ⁱⁱ—Zn1—O2	93.89 (7)
C13—C12—H12	109.1	O1—Zn1—O2	166.10 (6)
C14—C12—H12	109.1	N1—Zn1—O2	78.22 (6)
C12—C13—H13A	109.5	O4—Zn1—O2	87.52 (7)

O1—C1—C2—C11	−0.5 (4)	C13—C12—N1—C11	89.0 (2)
C10—C1—C2—C11	179.8 (2)	C14—C12—N1—C11	−150.37 (18)
O1—C1—C2—C3	178.2 (2)	C13—C12—N1—Zn1	−102.1 (2)
C10—C1—C2—C3	−1.4 (3)	C14—C12—N1—Zn1	18.5 (2)
C1—C2—C3—C4	179.0 (2)	C2—C1—O1—Zn1	−20.7 (3)
C11—C2—C3—C4	−2.2 (4)	C10—C1—O1—Zn1	158.98 (16)
C1—C2—C3—C8	−1.5 (3)	O3—C14—O2—Zn1	−175.97 (16)
C11—C2—C3—C8	177.3 (2)	C12—C14—O2—Zn1	4.9 (2)
C8—C3—C4—C5	−1.7 (4)	O2—C14—O3—Zn1ⁱ	16.7 (3)
C2—C3—C4—C5	177.8 (3)	C12—C14—O3—Zn1ⁱ	−164.18 (13)
C3—C4—C5—C6	−0.8 (4)	Zn1—O4—S1—C15	23.79 (18)
C4—C5—C6—C7	2.2 (4)	Zn1—O4—S1—C16	−80.64 (17)
C5—C6—C7—C8	−1.1 (4)	C1—O1—Zn1—O3ⁱⁱ	165.79 (17)
C4—C3—C8—C9	−177.1 (2)	C1—O1—Zn1—N1	26.85 (17)
C2—C3—C8—C9	3.4 (3)	C1—O1—Zn1—O4	−91.96 (18)
C4—C3—C8—C7	2.8 (3)	C1—O1—Zn1—O2	12.5 (4)
C2—C3—C8—C7	−176.7 (2)	C11—N1—Zn1—O3ⁱⁱ	−122.75 (17)
C6—C7—C8—C9	178.4 (2)	C12—N1—Zn1—O3ⁱⁱ	69.40 (17)
C6—C7—C8—C3	−1.4 (4)	C11—N1—Zn1—O1	−21.72 (17)
C3—C8—C9—C10	−2.4 (4)	C12—N1—Zn1—O1	170.43 (14)
C7—C8—C9—C10	177.7 (2)	C11—N1—Zn1—O4	74.31 (18)
C8—C9—C10—C1	−0.6 (4)	C12—N1—Zn1—O4	−93.54 (15)
O1—C1—C10—C9	−177.2 (2)	C11—N1—Zn1—O2	154.80 (18)
C2—C1—C10—C9	2.5 (3)	C12—N1—Zn1—O2	−13.05 (14)
C1—C2—C11—N1	5.6 (4)	S1—O4—Zn1—O3ⁱⁱ	−170.20 (14)
C3—C2—C11—N1	−173.2 (2)	S1—O4—Zn1—O1	89.82 (14)
N1—C12—C14—O2	−15.1 (3)	S1—O4—Zn1—N1	−1.61 (17)
C13—C12—C14—O2	106.5 (2)	S1—O4—Zn1—O2	−76.72 (14)
N1—C12—C14—O3	165.76 (17)	C14—O2—Zn1—O3ⁱⁱ	−134.50 (15)
C13—C12—C14—O3	−72.7 (3)	C14—O2—Zn1—O1	19.0 (4)
C2—C11—N1—C12	178.6 (2)	C14—O2—Zn1—N1	4.39 (14)
C2—C11—N1—Zn1	10.9 (3)	C14—O2—Zn1—O4	124.51 (15)

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

Experimental details

Crystal data
Chemical formula	[Zn(C₁₄H₁₁NO₃)(C₂H₆OS)]
M_r	384.74
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	291
a, b, c (Å)	9.676 (4), 7.651 (4), 11.715 (5)
β (°)	106.256 (15)
V (Å³)	832.6 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.62
Crystal size (mm)	0.31 × 0.28 × 0.24

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.633, 0.697
No. of measured, independent and observed [I > 2σ(I)] reflections	8191, 3729, 3533
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.056, 1.06
No. of reflections	3729
No. of parameters	211
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.19
Absolute structure	Flack (1983), 1675 Friedel pairs
Absolute structure parameter	0.006 (8)

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	2.0119 (18)	O3—Zn1ⁱ	1.9560 (15)
O1—Zn1	2.0040 (15)	O4—Zn1	2.0520 (17)
O2—Zn1	2.1891 (16)

O3ⁱⁱ—Zn1—O1	98.54 (7)	N1—Zn1—O4	118.82 (7)
O3ⁱⁱ—Zn1—N1	138.57 (7)	O3ⁱⁱ—Zn1—O2	93.89 (7)
O1—Zn1—N1	88.32 (7)	O1—Zn1—O2	166.10 (6)
O3ⁱⁱ—Zn1—O4	101.12 (7)	N1—Zn1—O2	78.22 (6)
O1—Zn1—O4	96.09 (7)	O4—Zn1—O2	87.52 (7)

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

Acknowledgements

This work was supported by the National Natural Science Foundation of China (No. 20272011).

References

Audriceth, L. F., Scott, E. S. & Kipper, P. S. (1954). J. Org. Chem. 19, 733–741. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals 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

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