Bis{μ-2-(1H-indol-3-yl)-N′-[1-(5-methyl-2-oxidophen­yl)ethyl­idene]­aceto­hydraz­idato}bis­[aqua­zinc(II)] dimethyl sulfoxide tetra­solvate

Zuraini, K.; Ali, H.M.; Puvaneswary, S.; Robinson, W.T.; Ng, S.W.

doi:10.1107/S1600536808022034

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page m1047

doi:10.1107/S1600536808022034

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Bis{μ-2-(1H-indol-3-yl)-N′-[1-(5-methyl-2-oxidophenyl)ethylidene]acetohydrazidato}bis[aquazinc(II)] dimethyl sulfoxide tetrasolvate

Kadir Zuraini,^a Hapipah M. Ali,^a Subramaniam Puvaneswary,^a Ward T. Robinson ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 10 July 2008; accepted 15 July 2008; online 19 July 2008)

The dinuclear title compound, [Zn₂(C₁₉H₁₇N₃O₂)₂(H₂O)₂]·4C₂H₆OS, lies about a center of inversion. The deprotonated monoanion O,N,O-chelates the Zn atom; the hydroxy O atom also engages in bonding to the symmetry-related Zn atom so that one N and three O atoms form a square around the metal. The coordination geometry is square-pyramidal, with the apical site occupied by a water molecule. Hydrogen bonds, with the water molecule serving as donor atom, lead to the formation of a linear chain motif. There is an N—H⋯O hydrogen bond between the complex molecule and solvent O atom.

Related literature

For the structure of a similar Schiff base ligand, see: Ali et al. (2008 ).

Experimental

Crystal data

[Zn₂(C₁₉H₁₇N₃O₂)₂(H₂O)₂]·4C₂H₆OS
M_r = 1118.00
Triclinic, $[P \overline 1]$
a = 8.5271 (2) Å
b = 8.8849 (3) Å
c = 16.8279 (5) Å
α = 85.519 (2)°
β = 84.920 (2)°
γ = 84.251 (2)°
V = 1260.44 (6) Å³
Z = 1
Mo Kα radiation
μ = 1.18 mm⁻¹
T = 100 (2) K
0.19 × 0.03 × 0.03 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.807, T_max = 0.966
13526 measured reflections
5739 independent reflections
3700 reflections with I > 2σ(I)
R_int = 0.076

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.157
S = 0.99
5739 reflections
313 parameters
H-atom parameters constrained
Δρ_max = 1.18 e Å⁻³
Δρ_min = −1.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯O3	0.84	1.80	2.608 (4)	161
O1W—H1W2⋯N2ⁱ	0.84	1.87	2.703 (4)	173
N3—H3N⋯O4	0.88	1.95	2.822 (5)	172
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2008 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808022034/si2100sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808022034/si2100Isup2.hkl

checkCIF report

Comment top

The present study continues with a study on 1-(2-hydroxy-5-methylphenyl)ethanone [(1H-3-indolyl)acetyl]hydrazone (Ali et al., 2008). The present study reports the zinc derivative of a similar ligand (Scheme I, Fig. 1). The dinuclear compound lies about a center-of-inversion. The deprotonated monoanion O,N,O chelates to the Zn atom; the hydroxy oxygen atom also engages in bonding to the symmetry-related Zn atom so that one nitrogen and oxygen atoms comprise a square around the metal. The geometry is a square pyramid, with the apical site occupied by a water molecule. Hydrogen bonds, with the water molecule serving as donor atom, leads to the formation of a linear chain motif.

Related literature top

For the structure of a similar Schiff base ligand, see: Ali et al. (2008).

Experimental top

Indole-3- acetic acid hydrazide (0.55 g, 4 mmol) and 5-methyl-2-hydroxyacetophenone (0.52 g, 4 mmol) were heated in ethanol for 2 h. The solvent was removed to give the Schiff base. The ligand (0.55 g, 4 mmol) and zinc acetate (0.26 g, 2 mmol) were dissolved in basified ethanol and heated for 5 h. The yellow solid was that was obtained was recrystallized from DMSO.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) plot of the dinuclear compound at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. The compound lies about a center of inversion, and unlabeled atoms are related to their labeled equivalents by 1 – x, 1 – y, 1 – z.

Bis{µ-2-(1H-indol-3-yl)-N'-[1-(5-methyl-2- oxidophenyl)ethylidene]acetohydrazidato}bis[aquazinc(II)] dimethyl sulfoxide tetrasolvate top

Crystal data top

[Zn₂(C₁₉H₁₇N₃O₂)₂(H₂O)₂]·4C₂H₆OS	Z = 1
M_r = 1118.00	F(000) = 584
Triclinic, P1	D_x = 1.473 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5271 (2) Å	Cell parameters from 2055 reflections
b = 8.8849 (3) Å	θ = 2.4–21.0°
c = 16.8279 (5) Å	µ = 1.18 mm⁻¹
α = 85.519 (2)°	T = 100 K
β = 84.920 (2)°	Block, yellow
γ = 84.251 (2)°	0.19 × 0.03 × 0.03 mm
V = 1260.44 (6) Å³

Data collection top

Bruker SMART APEX diffractometer	5739 independent reflections
Radiation source: fine-focus sealed tube	3700 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.077
ω scans	θ_max = 27.5°, θ_min = 1.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.807, T_max = 0.966	k = −11→9
13526 measured reflections	l = −21→21

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.157	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0772P)²] where P = (F_o² + 2F_c²)/3
5739 reflections	(Δ/σ)_max = 0.001
313 parameters	Δρ_max = 1.18 e Å⁻³
0 restraints	Δρ_min = −1.24 e Å⁻³

Crystal data top

[Zn₂(C₁₉H₁₇N₃O₂)₂(H₂O)₂]·4C₂H₆OS	γ = 84.251 (2)°
M_r = 1118.00	V = 1260.44 (6) Å³
Triclinic, P1	Z = 1
a = 8.5271 (2) Å	Mo Kα radiation
b = 8.8849 (3) Å	µ = 1.18 mm⁻¹
c = 16.8279 (5) Å	T = 100 K
α = 85.519 (2)°	0.19 × 0.03 × 0.03 mm
β = 84.920 (2)°

Data collection top

Bruker SMART APEX diffractometer	5739 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3700 reflections with I > 2σ(I)
T_min = 0.807, T_max = 0.966	R_int = 0.077
13526 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.157	H-atom parameters constrained
S = 0.99	Δρ_max = 1.18 e Å⁻³
5739 reflections	Δρ_min = −1.24 e Å⁻³
313 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Zn1	0.32563 (6)	0.51110 (6)	0.47468 (3)	0.01466 (16)
S2	0.28628 (14)	0.71165 (15)	−0.05107 (7)	0.0237 (3)
S1	0.51759 (13)	0.81274 (15)	0.61958 (7)	0.0223 (3)
O1	0.4553 (3)	0.4370 (4)	0.56890 (17)	0.0159 (7)
O2	0.2019 (3)	0.5011 (4)	0.37781 (18)	0.0213 (7)
O3	0.3597 (4)	0.8802 (4)	0.5929 (2)	0.0338 (9)
O4	0.3710 (4)	0.6688 (4)	0.02322 (19)	0.0237 (8)
O1W	0.2288 (3)	0.7174 (4)	0.49948 (18)	0.0198 (7)
H1W1	0.2774	0.7502	0.5348	0.030*
H1W2	0.1334	0.7129	0.5162	0.030*
N1	0.1821 (4)	0.3402 (4)	0.5139 (2)	0.0135 (8)
N2	0.0796 (4)	0.3130 (4)	0.4563 (2)	0.0147 (8)
N3	0.2308 (5)	0.4574 (5)	0.1345 (2)	0.0264 (10)
H3N	0.2808	0.5159	0.0981	0.032*
C1	0.4099 (5)	0.3577 (5)	0.6363 (2)	0.0144 (9)
C2	0.4983 (5)	0.3584 (5)	0.7028 (2)	0.0179 (10)
H2	0.5895	0.4127	0.6978	0.021*
C3	0.4569 (5)	0.2829 (5)	0.7751 (3)	0.0180 (10)
H3	0.5204	0.2848	0.8185	0.022*
C4	0.3218 (5)	0.2035 (5)	0.7849 (2)	0.0173 (9)
C5	0.2384 (5)	0.1992 (5)	0.7189 (2)	0.0158 (9)
H5	0.1486	0.1428	0.7247	0.019*
C6	0.2765 (5)	0.2724 (5)	0.6434 (2)	0.0148 (9)
C7	0.2737 (6)	0.1222 (6)	0.8645 (3)	0.0255 (11)
H7A	0.1851	0.0629	0.8584	0.038*
H7B	0.2415	0.1969	0.9041	0.038*
H7C	0.3635	0.0543	0.8824	0.038*
C8	0.1777 (5)	0.2507 (5)	0.5786 (2)	0.0139 (9)
C9	0.0720 (5)	0.1235 (5)	0.5894 (3)	0.0201 (10)
H9A	0.0518	0.0925	0.5369	0.030*
H9B	−0.0285	0.1580	0.6182	0.030*
H9C	0.1237	0.0371	0.6200	0.030*
C10	0.1006 (5)	0.4035 (5)	0.3904 (3)	0.0166 (9)
C11	−0.0086 (5)	0.3896 (5)	0.3254 (2)	0.0170 (10)
H11A	−0.0626	0.2958	0.3372	0.020*
H11B	−0.0906	0.4768	0.3252	0.020*
C12	0.0803 (5)	0.3853 (5)	0.2444 (2)	0.0166 (9)
C13	0.1430 (6)	0.5047 (6)	0.2012 (3)	0.0244 (11)
H13	0.1275	0.6067	0.2156	0.029*
C14	0.1322 (5)	0.2547 (5)	0.2012 (2)	0.0164 (9)
C15	0.1120 (5)	0.0994 (6)	0.2144 (3)	0.0207 (10)
H15	0.0459	0.0636	0.2588	0.025*
C16	0.1893 (6)	0.0001 (6)	0.1621 (3)	0.0265 (11)
H16	0.1765	−0.1051	0.1710	0.032*
C17	0.2869 (5)	0.0515 (6)	0.0958 (3)	0.0261 (11)
H17	0.3397	−0.0200	0.0610	0.031*
C18	0.3076 (5)	0.2019 (6)	0.0802 (3)	0.0230 (11)
H18	0.3729	0.2365	0.0351	0.028*
C19	0.2282 (5)	0.3032 (6)	0.1335 (3)	0.0193 (10)
C20	0.6333 (6)	0.9686 (6)	0.6179 (3)	0.0312 (12)
H20A	0.6492	1.0129	0.5630	0.047*
H20B	0.7361	0.9336	0.6380	0.047*
H20C	0.5784	1.0453	0.6519	0.047*
C21	0.4833 (7)	0.7774 (8)	0.7244 (3)	0.0400 (15)
H21A	0.4050	0.7035	0.7359	0.060*
H21B	0.4436	0.8722	0.7485	0.060*
H21C	0.5825	0.7370	0.7468	0.060*
C22	0.2380 (7)	0.5408 (7)	−0.0869 (3)	0.0395 (14)
H22A	0.3354	0.4786	−0.1030	0.059*
H22B	0.1751	0.5646	−0.1330	0.059*
H22C	0.1768	0.4848	−0.0444	0.059*
C23	0.0906 (6)	0.7843 (7)	−0.0178 (3)	0.0329 (13)
H23A	0.0953	0.8749	0.0113	0.049*
H23B	0.0403	0.7071	0.0177	0.049*
H23C	0.0287	0.8109	−0.0641	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0079 (2)	0.0202 (3)	0.0158 (3)	−0.0058 (2)	0.00131 (18)	0.0025 (2)
S2	0.0200 (6)	0.0270 (7)	0.0230 (6)	−0.0063 (5)	0.0020 (5)	0.0058 (5)
S1	0.0161 (5)	0.0233 (7)	0.0278 (6)	0.0003 (5)	−0.0040 (5)	−0.0040 (5)
O1	0.0111 (14)	0.0222 (19)	0.0141 (14)	−0.0070 (13)	0.0009 (12)	0.0050 (13)
O2	0.0153 (15)	0.030 (2)	0.0195 (16)	−0.0110 (14)	0.0012 (13)	0.0041 (14)
O3	0.0222 (18)	0.035 (2)	0.047 (2)	0.0040 (16)	−0.0174 (17)	−0.0109 (18)
O4	0.0163 (16)	0.025 (2)	0.0291 (18)	−0.0088 (14)	0.0001 (14)	0.0103 (15)
O1W	0.0107 (14)	0.0250 (19)	0.0238 (16)	−0.0057 (13)	−0.0002 (13)	0.0012 (14)
N1	0.0096 (16)	0.017 (2)	0.0142 (17)	−0.0018 (15)	0.0008 (14)	−0.0016 (15)
N2	0.0096 (16)	0.017 (2)	0.0178 (18)	−0.0033 (15)	0.0011 (14)	−0.0021 (15)
N3	0.034 (2)	0.028 (3)	0.018 (2)	−0.014 (2)	−0.0004 (18)	0.0056 (18)
C1	0.0089 (19)	0.016 (2)	0.017 (2)	−0.0029 (17)	0.0038 (16)	0.0011 (17)
C2	0.011 (2)	0.024 (3)	0.019 (2)	−0.0063 (19)	0.0049 (17)	−0.0035 (19)
C3	0.016 (2)	0.021 (3)	0.017 (2)	−0.0057 (19)	−0.0003 (18)	0.0014 (18)
C4	0.019 (2)	0.019 (3)	0.013 (2)	−0.0018 (19)	0.0021 (17)	0.0032 (18)
C5	0.010 (2)	0.017 (3)	0.019 (2)	−0.0036 (18)	0.0036 (17)	0.0028 (18)
C6	0.0098 (19)	0.015 (2)	0.019 (2)	−0.0030 (17)	0.0002 (17)	0.0018 (18)
C7	0.026 (3)	0.028 (3)	0.022 (2)	−0.010 (2)	0.000 (2)	0.006 (2)
C8	0.0078 (19)	0.013 (2)	0.019 (2)	−0.0016 (17)	0.0057 (16)	0.0034 (18)
C9	0.014 (2)	0.024 (3)	0.023 (2)	−0.009 (2)	−0.0042 (18)	0.003 (2)
C10	0.0089 (19)	0.021 (3)	0.020 (2)	−0.0030 (18)	0.0020 (17)	−0.0019 (19)
C11	0.0093 (19)	0.024 (3)	0.018 (2)	−0.0017 (19)	0.0008 (17)	−0.0018 (19)
C12	0.014 (2)	0.022 (3)	0.014 (2)	−0.0057 (19)	−0.0026 (17)	0.0037 (18)
C13	0.031 (3)	0.022 (3)	0.021 (2)	−0.007 (2)	−0.007 (2)	0.003 (2)
C14	0.011 (2)	0.024 (3)	0.015 (2)	−0.0040 (19)	−0.0031 (17)	0.0025 (18)
C15	0.018 (2)	0.024 (3)	0.020 (2)	−0.006 (2)	−0.0002 (18)	−0.0007 (19)
C16	0.027 (3)	0.018 (3)	0.035 (3)	−0.004 (2)	−0.007 (2)	0.000 (2)
C17	0.021 (2)	0.030 (3)	0.028 (3)	−0.001 (2)	−0.002 (2)	−0.010 (2)
C18	0.012 (2)	0.039 (3)	0.019 (2)	−0.006 (2)	0.0002 (18)	−0.005 (2)
C19	0.015 (2)	0.028 (3)	0.016 (2)	−0.008 (2)	−0.0007 (17)	0.0033 (19)
C20	0.029 (3)	0.027 (3)	0.039 (3)	−0.002 (2)	−0.009 (2)	0.000 (2)
C21	0.031 (3)	0.058 (4)	0.031 (3)	−0.010 (3)	−0.001 (2)	0.005 (3)
C22	0.048 (4)	0.035 (4)	0.036 (3)	−0.004 (3)	−0.003 (3)	−0.009 (3)
C23	0.020 (3)	0.036 (3)	0.043 (3)	0.002 (2)	−0.009 (2)	−0.005 (3)

Geometric parameters (Å, º) top

Zn1—O1	2.043 (3)	C7—H7B	0.9800
Zn1—O1ⁱ	2.029 (3)	C7—H7C	0.9800
Zn1—O2	2.031 (3)	C8—C9	1.506 (6)
Zn1—O1w	1.993 (3)	C9—H9A	0.9800
Zn1—N1	2.077 (4)	C9—H9B	0.9800
Zn1—Zn1ⁱ	3.1485 (9)	C9—H9C	0.9800
S2—O4	1.503 (3)	C10—C11	1.518 (5)
S2—C22	1.775 (6)	C11—C12	1.502 (6)
S2—C23	1.786 (5)	C11—H11A	0.9900
S1—O3	1.509 (3)	C11—H11B	0.9900
S1—C21	1.771 (5)	C12—C13	1.365 (6)
S1—C20	1.776 (5)	C12—C14	1.428 (6)
O1—C1	1.335 (5)	C13—H13	0.9500
O1—Zn1ⁱ	2.029 (3)	C14—C15	1.406 (6)
O2—C10	1.277 (5)	C14—C19	1.408 (6)
O1W—H1W1	0.8400	C15—C16	1.374 (7)
O1W—H1W2	0.8400	C15—H15	0.9500
N1—C8	1.297 (5)	C16—C17	1.408 (7)
N1—N2	1.410 (4)	C16—H16	0.9500
N2—C10	1.328 (6)	C17—C18	1.368 (7)
N3—C13	1.363 (6)	C17—H17	0.9500
N3—C19	1.374 (6)	C18—C19	1.404 (7)
N3—H3N	0.8800	C18—H18	0.9500
C1—C2	1.404 (6)	C20—H20A	0.9800
C1—C6	1.420 (6)	C20—H20B	0.9800
C2—C3	1.377 (6)	C20—H20C	0.9800
C2—H2	0.9500	C21—H21A	0.9800
C3—C4	1.401 (6)	C21—H21B	0.9800
C3—H3	0.9500	C21—H21C	0.9800
C4—C5	1.375 (6)	C22—H22A	0.9800
C4—C7	1.515 (6)	C22—H22B	0.9800
C5—C6	1.408 (6)	C22—H22C	0.9800
C5—H5	0.9500	C23—H23A	0.9800
C6—C8	1.472 (5)	C23—H23B	0.9800
C7—H7A	0.9800	C23—H23C	0.9800

O1—Zn1—O1ⁱ	78.7 (1)	C8—C9—H9B	109.5
O1—Zn1—O2	158.8 (1)	H9A—C9—H9B	109.5
O1—Zn1—O1w	105.3 (1)	C8—C9—H9C	109.5
O1—Zn1—N1	86.3 (1)	H9A—C9—H9C	109.5
O1ⁱ—Zn1—O2	106.0 (1)	H9B—C9—H9C	109.5
O1ⁱ—Zn1—O1w	99.5 (1)	O2—C10—N2	126.0 (4)
O1ⁱ—Zn1—N1	146.5 (1)	O2—C10—C11	118.0 (4)
O2—Zn1—O1w	94.5 (1)	N2—C10—C11	116.0 (4)
O2—Zn1—N1	78.7 (1)	C12—C11—C10	111.6 (3)
O1W—Zn1—N1	113.4 (1)	C12—C11—H11A	109.3
O1W—Zn1—Zn1ⁱ	106.07 (8)	C10—C11—H11A	109.3
O1ⁱ—Zn1—Zn1ⁱ	39.51 (8)	C12—C11—H11B	109.3
O2—Zn1—Zn1ⁱ	141.51 (9)	C10—C11—H11B	109.3
O1—Zn1—Zn1ⁱ	39.19 (8)	H11A—C11—H11B	108.0
N1—Zn1—Zn1ⁱ	119.67 (10)	C13—C12—C14	106.0 (4)
O4—S2—C22	107.0 (2)	C13—C12—C11	126.2 (4)
O4—S2—C23	106.1 (2)	C14—C12—C11	127.4 (4)
C22—S2—C23	97.8 (3)	N3—C13—C12	110.7 (5)
O3—S1—C21	104.4 (2)	N3—C13—H13	124.7
O3—S1—C20	105.1 (2)	C12—C13—H13	124.7
C21—S1—C20	99.1 (3)	C15—C14—C19	118.5 (4)
C1—O1—Zn1ⁱ	129.8 (2)	C15—C14—C12	134.2 (4)
C1—O1—Zn1	128.3 (2)	C19—C14—C12	107.2 (4)
Zn1ⁱ—O1—Zn1	101.30 (12)	C16—C15—C14	119.1 (4)
C10—O2—Zn1	111.6 (3)	C16—C15—H15	120.4
Zn1—O1W—H1W1	109.5	C14—C15—H15	120.4
Zn1—O1W—H1W2	109.5	C15—C16—C17	121.1 (5)
H1W1—O1W—H1W2	109.5	C15—C16—H16	119.4
C8—N1—N2	116.0 (4)	C17—C16—H16	119.4
C8—N1—Zn1	131.5 (3)	C18—C17—C16	121.5 (5)
N2—N1—Zn1	112.4 (3)	C18—C17—H17	119.2
C10—N2—N1	111.2 (3)	C16—C17—H17	119.2
C13—N3—C19	108.6 (4)	C17—C18—C19	117.2 (4)
C13—N3—H3N	125.7	C17—C18—H18	121.4
C19—N3—H3N	125.7	C19—C18—H18	121.4
O1—C1—C2	118.6 (4)	N3—C19—C18	130.0 (4)
O1—C1—C6	122.8 (4)	N3—C19—C14	107.5 (4)
C2—C1—C6	118.6 (4)	C18—C19—C14	122.5 (5)
C3—C2—C1	122.1 (4)	S1—C20—H20A	109.5
C3—C2—H2	118.9	S1—C20—H20B	109.5
C1—C2—H2	118.9	H20A—C20—H20B	109.5
C2—C3—C4	120.4 (4)	S1—C20—H20C	109.5
C2—C3—H3	119.8	H20A—C20—H20C	109.5
C4—C3—H3	119.8	H20B—C20—H20C	109.5
C5—C4—C3	117.2 (4)	S1—C21—H21A	109.5
C5—C4—C7	121.9 (4)	S1—C21—H21B	109.5
C3—C4—C7	120.9 (4)	H21A—C21—H21B	109.5
C4—C5—C6	124.7 (4)	S1—C21—H21C	109.5
C4—C5—H5	117.7	H21A—C21—H21C	109.5
C6—C5—H5	117.7	H21B—C21—H21C	109.5
C5—C6—C1	116.8 (4)	S2—C22—H22A	109.5
C5—C6—C8	117.3 (4)	S2—C22—H22B	109.5
C1—C6—C8	125.8 (4)	H22A—C22—H22B	109.5
C4—C7—H7A	109.5	S2—C22—H22C	109.5
C4—C7—H7B	109.5	H22A—C22—H22C	109.5
H7A—C7—H7B	109.5	H22B—C22—H22C	109.5
C4—C7—H7C	109.5	S2—C23—H23A	109.5
H7A—C7—H7C	109.5	S2—C23—H23B	109.5
H7B—C7—H7C	109.5	H23A—C23—H23B	109.5
N1—C8—C6	120.3 (4)	S2—C23—H23C	109.5
N1—C8—C9	121.1 (4)	H23A—C23—H23C	109.5
C6—C8—C9	118.6 (4)	H23B—C23—H23C	109.5
C8—C9—H9A	109.5

O1W—Zn1—O1—C1	91.0 (4)	C2—C1—C6—C5	2.7 (6)
O1ⁱ—Zn1—O1—C1	−172.2 (4)	O1—C1—C6—C8	4.2 (7)
O2—Zn1—O1—C1	−66.9 (5)	C2—C1—C6—C8	−175.6 (4)
N1—Zn1—O1—C1	−22.3 (4)	N2—N1—C8—C6	−178.2 (4)
Zn1ⁱ—Zn1—O1—C1	−172.2 (4)	Zn1—N1—C8—C6	6.6 (6)
O1W—Zn1—O1—Zn1ⁱ	−96.87 (14)	N2—N1—C8—C9	1.6 (6)
O1ⁱ—Zn1—O1—Zn1ⁱ	0.0	Zn1—N1—C8—C9	−173.6 (3)
O2—Zn1—O1—Zn1ⁱ	105.2 (3)	C5—C6—C8—N1	164.2 (4)
N1—Zn1—O1—Zn1ⁱ	149.86 (15)	C1—C6—C8—N1	−17.5 (7)
O1W—Zn1—O2—C10	−111.0 (3)	C5—C6—C8—C9	−15.6 (6)
O1ⁱ—Zn1—O2—C10	147.8 (3)	C1—C6—C8—C9	162.7 (4)
O1—Zn1—O2—C10	47.6 (5)	Zn1—O2—C10—N2	−2.8 (6)
N1—Zn1—O2—C10	2.0 (3)	Zn1—O2—C10—C11	176.2 (3)
Zn1ⁱ—Zn1—O2—C10	126.0 (3)	N1—N2—C10—O2	1.7 (6)
O1W—Zn1—N1—C8	−95.9 (4)	N1—N2—C10—C11	−177.3 (3)
O1ⁱ—Zn1—N1—C8	72.1 (5)	O2—C10—C11—C12	45.9 (6)
O2—Zn1—N1—C8	174.1 (4)	N2—C10—C11—C12	−135.0 (4)
O1—Zn1—N1—C8	9.1 (4)	C10—C11—C12—C13	−72.6 (6)
Zn1ⁱ—Zn1—N1—C8	30.5 (4)	C10—C11—C12—C14	99.6 (5)
O1W—Zn1—N1—N2	88.7 (3)	C19—N3—C13—C12	−0.7 (5)
O1ⁱ—Zn1—N1—N2	−103.2 (3)	C14—C12—C13—N3	−0.3 (5)
O2—Zn1—N1—N2	−1.2 (2)	C11—C12—C13—N3	173.2 (4)
O1—Zn1—N1—N2	−166.2 (3)	C13—C12—C14—C15	178.4 (5)
Zn1ⁱ—Zn1—N1—N2	−144.8 (2)	C11—C12—C14—C15	4.9 (7)
C8—N1—N2—C10	−175.8 (4)	C13—C12—C14—C19	1.2 (4)
Zn1—N1—N2—C10	0.3 (4)	C11—C12—C14—C19	−172.3 (4)
Zn1ⁱ—O1—C1—C2	29.5 (6)	C19—C14—C15—C16	1.5 (6)
Zn1—O1—C1—C2	−160.5 (3)	C12—C14—C15—C16	−175.4 (4)
Zn1ⁱ—O1—C1—C6	−150.3 (3)	C14—C15—C16—C17	−0.4 (7)
Zn1—O1—C1—C6	19.7 (6)	C15—C16—C17—C18	−0.7 (7)
O1—C1—C2—C3	178.2 (4)	C16—C17—C18—C19	0.5 (6)
C6—C1—C2—C3	−2.0 (7)	C13—N3—C19—C18	−175.9 (4)
C1—C2—C3—C4	−0.9 (7)	C13—N3—C19—C14	1.4 (5)
C2—C3—C4—C5	2.8 (7)	C17—C18—C19—N3	177.6 (4)
C2—C3—C4—C7	−179.0 (4)	C17—C18—C19—C14	0.7 (6)
C3—C4—C5—C6	−2.0 (7)	C15—C14—C19—N3	−179.3 (4)
C7—C4—C5—C6	179.8 (4)	C12—C14—C19—N3	−1.6 (4)
C4—C5—C6—C1	−0.8 (7)	C15—C14—C19—C18	−1.8 (6)
C4—C5—C6—C8	177.7 (4)	C12—C14—C19—C18	175.9 (4)
O1—C1—C6—C5	−177.5 (4)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O3	0.84	1.80	2.608 (4)	161
O1W—H1W2···N2ⁱⁱ	0.84	1.87	2.703 (4)	173
N3—H3N···O4	0.88	1.95	2.822 (5)	172

Symmetry code: (ii) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Zn₂(C₁₉H₁₇N₃O₂)₂(H₂O)₂]·4C₂H₆OS
M_r	1118.00
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.5271 (2), 8.8849 (3), 16.8279 (5)
α, β, γ (°)	85.519 (2), 84.920 (2), 84.251 (2)
V (Å³)	1260.44 (6)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	1.18
Crystal size (mm)	0.19 × 0.03 × 0.03

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.807, 0.966
No. of measured, independent and observed [I > 2σ(I)] reflections	13526, 5739, 3700
R_int	0.077
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.157, 0.99
No. of reflections	5739
No. of parameters	313
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.18, −1.24

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O3	0.84	1.80	2.608 (4)	161
O1W—H1W2···N2ⁱ	0.84	1.87	2.703 (4)	173
N3—H3N···O4	0.88	1.95	2.822 (5)	172

Symmetry code: (i) −x, −y+1, −z+1.

Acknowledgements

We thank the Science Fund (12-02-03-2031, 12-02-03-2051) and the University of Malaya (PJP) for supporting this study. We are grateful to the University of Malaya for the purchase of the diffractometer.

References

Ali, H. M., Zuraini, K., Wan Jeffrey, B., Rizal, M. R. & Ng, S. W. (2008). Acta Cryst. E64, o912. Web of Science CSD CrossRef IUCr Journals Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2008). publCIF. In preparation. Google Scholar

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Volume 64| Part 8| August 2008| Page m1047

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

Bis{μ-2-(1H-indol-3-yl)-N′-[1-(5-methyl-2-oxidophen­yl)ethyl­­idene]­aceto­hydraz­idato}bis­­[aqua­zinc(II)] di­methyl sulfoxide tetra­solvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis{μ-2-(1H-indol-3-yl)-N′-[1-(5-methyl-2-oxidophenyl)ethylidene]acetohydrazidato}bis[aquazinc(II)] dimethyl sulfoxide tetrasolvate