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The ZnII ion in the title complex, [Zn(C9H4NO4S)(C3H4N2)2], is coordinated by an N atom and an O atom of a deprotonated tridentate Schiff base ligand, and two N atoms from two different imidazole ligands in a distorted tetra­hedral geometry. In the crystal structure, mol­ecules are connected via inter­molecular N—H...O hydrogen bonds, forming extended one-dimensional chains along [111].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807056097/lh2539sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807056097/lh2539Isup2.hkl
Contains datablock I

CCDC reference: 672644

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.023
  • wR factor = 0.060
  • Data-to-parameter ratio = 13.9

checkCIF/PLATON results

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Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.97 PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 100 Deg. PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT794_ALERT_5_G Check Predicted Bond Valency for Zn1 (2) 1.88
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Comment top

There is considerable interest in the study of Schiff-base complexes containing sulfur and complexes of amino acid Schiff-bases (Deng et al., 2006; Jiang et al., 2006; Casella et al., 1981,1986) due to their antiviral, anticancer and antibacterial activities. Herein, we report the synthesis and crystal structure of the title zinc(II) complex. The ZnII cation is coordinated by one N atom and one O atom of a deprotonated tridentate schiff base ligand and two N atoms (Fig.1 and Table.1) from two different 1H-Imidazole ligands in a distorted tetrahedral geometry. In the crystal structure, molecules are connected via intermolecular N—H···O hydrogen bonds to form extended one-dimensional chains along [111].

Related literature top

For related literature, see: Deng et al. (2006); Jiang et al. (2006); Casella et al. (1981, 1986); Li et al. (2005).

Experimental top

The potassium salt of the Schiff base ligand [(2-Hydroxy-benzylidene)-amino]-methanesulfonic acid, L, was synthesized according to the approach of Li et al. (2005). L (1.0 mmol) in 10 ml me thanol was added dropwise to a stirred solution of ZnCl2 (1.0 mmol) in 5 ml me thanol and 5 ml water. To this mixed solution, a solution of 1H-Imidazole (2.0 mmol) in 5 ml me thanol was added slowly. The resulting yellow solution was filtered and left to stand for two weeks to evaporate slowly at room temperature to give yellow prism-shaped single crystals in yield of 55%.

Refinement top

H atoms were fixed geometrically and allowed to ride on their attached atoms, with C—H distances 0.93Å and N—H distances 0.86 Å, and with Uiso(H) = 1.2Ueq(C,N).

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); 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: SHELXL97 (Sheldrick, 1997a).

Figures top
[Figure 1] Fig. 1. The molecular structure with displacement ellipsoids at the 30% probability level.
[Figure 2] Fig. 2. Part of the crystal structure showing hydrogen bonds as dashed lines. Only H stoms involved in hydrogen bonds are included.
Bis(1H-imidazole-κN3)[(2-oxidobenzylideneamino)methanesulfonato-\ κ2N,O]zinc(II) top
Crystal data top
[Zn(C9H4NO4S)(C3H4N2)2]Z = 2
Mr = 414.74F(000) = 424
Triclinic, P1Dx = 1.575 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.7931 (10) ÅCell parameters from 4316 reflections
b = 9.7881 (11) Åθ = 2.5–28.1°
c = 10.8602 (12) ŵ = 1.55 mm1
α = 90.010 (1)°T = 293 K
β = 107.443 (1)°Block, yellow
γ = 100.798 (1)°0.44 × 0.27 × 0.26 mm
V = 874.36 (17) Å3
Data collection top
Bruker SMART CCD
diffractometer
3151 independent reflections
Radiation source: fine-focus sealed tube2897 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.011
ϕ and ω scansθmax = 25.5°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1010
Tmin = 0.535, Tmax = 0.689k = 1111
6254 measured reflectionsl = 1313
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.023Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.060H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0287P)2 + 0.3794P]
where P = (Fo2 + 2Fc2)/3
3151 reflections(Δ/σ)max = 0.001
226 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.28 e Å3
Crystal data top
[Zn(C9H4NO4S)(C3H4N2)2]γ = 100.798 (1)°
Mr = 414.74V = 874.36 (17) Å3
Triclinic, P1Z = 2
a = 8.7931 (10) ÅMo Kα radiation
b = 9.7881 (11) ŵ = 1.55 mm1
c = 10.8602 (12) ÅT = 293 K
α = 90.010 (1)°0.44 × 0.27 × 0.26 mm
β = 107.443 (1)°
Data collection top
Bruker SMART CCD
diffractometer
3151 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2897 reflections with I > 2σ(I)
Tmin = 0.535, Tmax = 0.689Rint = 0.011
6254 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0230 restraints
wR(F2) = 0.060H-atom parameters constrained
S = 1.03Δρmax = 0.30 e Å3
3151 reflectionsΔρmin = 0.28 e Å3
226 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
xyzUiso*/Ueq
Zn10.38626 (3)0.74569 (2)0.14640 (2)0.03885 (8)
S10.13599 (5)0.93736 (5)0.20311 (4)0.03197 (11)
O10.46352 (18)0.68569 (16)0.00677 (13)0.0502 (4)
O20.00090 (15)0.84950 (14)0.10831 (13)0.0431 (3)
O30.08886 (16)1.05113 (15)0.26015 (13)0.0466 (3)
O40.23487 (17)0.85840 (15)0.29732 (13)0.0486 (3)
N10.31567 (17)0.91200 (15)0.05194 (14)0.0315 (3)
N20.2293 (2)0.57083 (16)0.15324 (16)0.0424 (4)
N30.0918 (2)0.35836 (19)0.0995 (2)0.0645 (6)
H3D0.05150.27900.05700.077*
N40.58586 (18)0.77884 (16)0.29863 (15)0.0380 (3)
N50.7630 (2)0.8389 (2)0.48859 (17)0.0518 (4)
H5D0.80370.86810.56860.062*
C10.4071 (2)0.71274 (19)0.11433 (18)0.0366 (4)
C20.3259 (2)0.82584 (18)0.15616 (17)0.0319 (4)
C30.2756 (2)0.8502 (2)0.28977 (18)0.0404 (4)
H30.22480.92490.31650.048*
C40.2998 (3)0.7668 (3)0.3805 (2)0.0535 (6)
H40.26610.78460.46770.064*
C50.3761 (3)0.6546 (3)0.3399 (2)0.0595 (6)
H50.39220.59690.40080.071*
C60.4275 (3)0.6282 (2)0.2113 (2)0.0515 (5)
H60.47740.55240.18740.062*
C70.2925 (2)0.92062 (18)0.07104 (17)0.0318 (4)
H70.24960.99610.10830.038*
C80.2696 (2)1.01987 (18)0.11775 (18)0.0352 (4)
H8A0.21541.07970.05520.042*
H8B0.36561.07670.17770.042*
C90.1900 (3)0.4635 (2)0.0680 (2)0.0524 (5)
H90.22620.46190.00400.063*
C100.0660 (3)0.3977 (3)0.2098 (3)0.0710 (7)
H100.00270.34460.25420.085*
C110.1507 (3)0.5295 (2)0.2425 (2)0.0584 (6)
H110.15490.58370.31430.070*
C120.7353 (2)0.7591 (2)0.2954 (2)0.0484 (5)
H120.75740.72560.22380.058*
C130.8448 (3)0.7960 (3)0.4130 (2)0.0575 (6)
H130.95480.79270.43730.069*
C140.6084 (2)0.8279 (2)0.41716 (19)0.0447 (5)
H140.52750.85160.44690.054*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.03963 (13)0.03755 (13)0.03377 (13)0.00707 (9)0.00320 (9)0.00622 (9)
S10.0283 (2)0.0370 (2)0.0294 (2)0.00515 (18)0.00793 (17)0.00237 (18)
O10.0591 (9)0.0575 (9)0.0392 (8)0.0312 (7)0.0107 (7)0.0089 (7)
O20.0332 (7)0.0474 (8)0.0420 (8)0.0030 (6)0.0080 (6)0.0078 (6)
O30.0415 (7)0.0540 (8)0.0458 (8)0.0122 (6)0.0137 (6)0.0137 (6)
O40.0477 (8)0.0555 (9)0.0404 (8)0.0137 (7)0.0079 (6)0.0113 (7)
N10.0296 (7)0.0332 (8)0.0329 (8)0.0062 (6)0.0113 (6)0.0015 (6)
N20.0434 (9)0.0341 (8)0.0414 (9)0.0044 (7)0.0022 (7)0.0023 (7)
N30.0509 (11)0.0362 (10)0.0857 (16)0.0013 (8)0.0055 (10)0.0120 (10)
N40.0356 (8)0.0416 (9)0.0340 (8)0.0070 (7)0.0068 (6)0.0021 (7)
N50.0479 (10)0.0639 (12)0.0346 (9)0.0091 (9)0.0002 (8)0.0052 (8)
C10.0316 (9)0.0400 (10)0.0383 (10)0.0070 (8)0.0107 (8)0.0013 (8)
C20.0267 (8)0.0359 (9)0.0330 (9)0.0031 (7)0.0107 (7)0.0028 (7)
C30.0366 (10)0.0478 (11)0.0361 (10)0.0067 (8)0.0112 (8)0.0074 (8)
C40.0529 (13)0.0749 (16)0.0321 (10)0.0108 (11)0.0130 (9)0.0001 (10)
C50.0618 (14)0.0724 (16)0.0473 (13)0.0186 (12)0.0176 (11)0.0147 (11)
C60.0509 (12)0.0529 (12)0.0530 (13)0.0208 (10)0.0131 (10)0.0061 (10)
C70.0257 (8)0.0332 (9)0.0364 (10)0.0051 (7)0.0097 (7)0.0069 (7)
C80.0344 (9)0.0317 (9)0.0408 (10)0.0044 (7)0.0146 (8)0.0006 (8)
C90.0478 (12)0.0448 (12)0.0559 (13)0.0118 (10)0.0012 (10)0.0087 (10)
C100.0640 (16)0.0527 (14)0.0826 (19)0.0103 (12)0.0151 (14)0.0083 (13)
C110.0642 (15)0.0490 (12)0.0534 (14)0.0061 (11)0.0157 (11)0.0004 (10)
C120.0427 (11)0.0582 (13)0.0456 (12)0.0140 (10)0.0130 (9)0.0052 (10)
C130.0357 (11)0.0732 (16)0.0588 (14)0.0152 (11)0.0042 (10)0.0051 (12)
C140.0405 (11)0.0548 (12)0.0389 (11)0.0097 (9)0.0120 (9)0.0017 (9)
Geometric parameters (Å, º) top
Zn1—O11.9679 (14)C1—C61.413 (3)
Zn1—N41.9914 (15)C1—C21.429 (3)
Zn1—N22.0039 (16)C2—C31.419 (3)
Zn1—N12.0212 (15)C2—C71.438 (2)
Zn1—O42.7447 (15)C3—C41.369 (3)
S1—O21.4551 (13)C3—H30.9300
S1—O41.4557 (14)C4—C51.396 (4)
S1—O31.4568 (14)C4—H40.9300
S1—C81.7856 (18)C5—C61.373 (3)
O1—C11.305 (2)C5—H50.9300
N1—C71.295 (2)C6—H60.9300
N1—C81.457 (2)C7—H70.9300
N2—C91.323 (3)C8—H8A0.9700
N2—C111.371 (3)C8—H8B0.9700
N3—C91.329 (3)C9—H90.9300
N3—C101.353 (4)C10—C111.352 (3)
N3—H3D0.8600C10—H100.9300
N4—C141.318 (2)C11—H110.9300
N4—C121.374 (3)C12—C131.349 (3)
N5—C141.332 (3)C12—H120.9300
N5—C131.355 (3)C13—H130.9300
N5—H5D0.8600C14—H140.9300
O1—Zn1—N4103.16 (6)C4—C3—C2121.92 (19)
O1—Zn1—N299.07 (7)C4—C3—H3119.0
N4—Zn1—N2113.05 (7)C2—C3—H3119.0
O1—Zn1—N192.46 (6)C3—C4—C5118.7 (2)
N4—Zn1—N1118.29 (6)C3—C4—H4120.6
N2—Zn1—N1122.81 (6)C5—C4—H4120.6
O1—Zn1—O4167.00 (5)C6—C5—C4121.1 (2)
N4—Zn1—O487.41 (5)C6—C5—H5119.5
N2—Zn1—O483.35 (6)C4—C5—H5119.5
N1—Zn1—O475.70 (5)C5—C6—C1122.0 (2)
O2—S1—O4113.12 (9)C5—C6—H6119.0
O2—S1—O3112.65 (8)C1—C6—H6119.0
O4—S1—O3114.02 (9)N1—C7—C2126.90 (16)
O2—S1—C8106.88 (8)N1—C7—H7116.5
O4—S1—C8104.07 (9)C2—C7—H7116.5
O3—S1—C8105.09 (9)N1—C8—S1108.39 (12)
C1—O1—Zn1124.51 (12)N1—C8—H8A110.0
S1—O4—Zn1100.45 (7)S1—C8—H8A110.0
C7—N1—C8116.93 (15)N1—C8—H8B110.0
C7—N1—Zn1122.22 (12)S1—C8—H8B110.0
C8—N1—Zn1120.44 (11)H8A—C8—H8B108.4
C9—N2—C11105.59 (19)N2—C9—N3110.7 (2)
C9—N2—Zn1123.10 (16)N2—C9—H9124.6
C11—N2—Zn1131.17 (14)N3—C9—H9124.6
C9—N3—C10108.18 (19)C11—C10—N3106.2 (2)
C9—N3—H3D125.9C11—C10—H10126.9
C10—N3—H3D125.9N3—C10—H10126.9
C14—N4—C12105.77 (17)C10—C11—N2109.2 (2)
C14—N4—Zn1129.98 (14)C10—C11—H11125.4
C12—N4—Zn1124.18 (13)N2—C11—H11125.4
C14—N5—C13107.93 (18)C13—C12—N4109.04 (19)
C14—N5—H5D126.0C13—C12—H12125.5
C13—N5—H5D126.0N4—C12—H12125.5
O1—C1—C6119.40 (18)C12—C13—N5106.47 (19)
O1—C1—C2123.67 (17)C12—C13—H13126.8
C6—C1—C2116.92 (18)N5—C13—H13126.8
C3—C2—C1119.28 (17)N4—C14—N5110.79 (18)
C3—C2—C7116.36 (16)N4—C14—H14124.6
C1—C2—C7124.35 (16)N5—C14—H14124.6
N4—Zn1—O1—C1146.69 (15)Zn1—O1—C1—C222.6 (3)
N2—Zn1—O1—C196.91 (16)O1—C1—C2—C3177.14 (17)
N1—Zn1—O1—C126.88 (16)C6—C1—C2—C32.0 (3)
O4—Zn1—O1—C12.9 (4)O1—C1—C2—C71.9 (3)
O2—S1—O4—Zn172.22 (8)C6—C1—C2—C7178.94 (17)
O3—S1—O4—Zn1157.33 (7)C1—C2—C3—C41.2 (3)
C8—S1—O4—Zn143.41 (8)C7—C2—C3—C4179.65 (18)
O1—Zn1—O4—S13.5 (3)C2—C3—C4—C50.1 (3)
N4—Zn1—O4—S1141.30 (8)C3—C4—C5—C60.6 (4)
N2—Zn1—O4—S1105.13 (8)C4—C5—C6—C10.3 (4)
N1—Zn1—O4—S121.23 (7)O1—C1—C6—C5177.6 (2)
O1—Zn1—N1—C718.53 (14)C2—C1—C6—C51.6 (3)
N4—Zn1—N1—C7124.90 (13)C8—N1—C7—C2178.97 (15)
N2—Zn1—N1—C783.91 (15)Zn1—N1—C7—C26.3 (2)
O4—Zn1—N1—C7156.06 (14)C3—C2—C7—N1174.17 (16)
O1—Zn1—N1—C8169.04 (13)C1—C2—C7—N16.8 (3)
N4—Zn1—N1—C862.67 (14)C7—N1—C8—S1126.47 (14)
N2—Zn1—N1—C888.51 (14)Zn1—N1—C8—S146.35 (15)
O4—Zn1—N1—C816.37 (12)O2—S1—C8—N157.15 (14)
O1—Zn1—N2—C97.38 (17)O4—S1—C8—N162.79 (14)
N4—Zn1—N2—C9115.96 (16)O3—S1—C8—N1177.07 (12)
N1—Zn1—N2—C991.51 (17)C11—N2—C9—N30.0 (2)
O4—Zn1—N2—C9159.73 (17)Zn1—N2—C9—N3176.16 (14)
O1—Zn1—N2—C11167.7 (2)C10—N3—C9—N20.3 (3)
N4—Zn1—N2—C1159.2 (2)C9—N3—C10—C110.5 (3)
N1—Zn1—N2—C1193.4 (2)N3—C10—C11—N20.5 (3)
O4—Zn1—N2—C1125.2 (2)C9—N2—C11—C100.3 (3)
O1—Zn1—N4—C14175.79 (17)Zn1—N2—C11—C10175.43 (17)
N2—Zn1—N4—C1478.22 (19)C14—N4—C12—C130.4 (3)
N1—Zn1—N4—C1475.66 (19)Zn1—N4—C12—C13177.64 (16)
O4—Zn1—N4—C143.43 (18)N4—C12—C13—N50.1 (3)
O1—Zn1—N4—C120.73 (17)C14—N5—C13—C120.2 (3)
N2—Zn1—N4—C12105.26 (17)C12—N4—C14—N50.5 (2)
N1—Zn1—N4—C12100.86 (17)Zn1—N4—C14—N5177.53 (14)
O4—Zn1—N4—C12173.09 (16)C13—N5—C14—N40.4 (3)
Zn1—O1—C1—C6158.23 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5D···O3i0.861.912.765 (2)173
N3—H3D···O2ii0.862.082.860 (2)151
Symmetry codes: (i) x+1, y+2, z+1; (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formula[Zn(C9H4NO4S)(C3H4N2)2]
Mr414.74
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)8.7931 (10), 9.7881 (11), 10.8602 (12)
α, β, γ (°)90.010 (1), 107.443 (1), 100.798 (1)
V3)874.36 (17)
Z2
Radiation typeMo Kα
µ (mm1)1.55
Crystal size (mm)0.44 × 0.27 × 0.26
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.535, 0.689
No. of measured, independent and
observed [I > 2σ(I)] reflections
6254, 3151, 2897
Rint0.011
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.023, 0.060, 1.03
No. of reflections3151
No. of parameters226
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.30, 0.28

Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).

Selected geometric parameters (Å, º) top
Zn1—O11.9679 (14)Zn1—N22.0039 (16)
Zn1—N41.9914 (15)Zn1—N12.0212 (15)
O1—Zn1—N4103.16 (6)N2—Zn1—N1122.81 (6)
O1—Zn1—N299.07 (7)O1—Zn1—O4167.00 (5)
N4—Zn1—N2113.05 (7)N4—Zn1—O487.41 (5)
O1—Zn1—N192.46 (6)N2—Zn1—O483.35 (6)
N4—Zn1—N1118.29 (6)N1—Zn1—O475.70 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5D···O3i0.861.912.765 (2)173.3
N3—H3D···O2ii0.862.082.860 (2)150.9
Symmetry codes: (i) x+1, y+2, z+1; (ii) x, y+1, z.
 

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