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In the title compound, [Zn(C2H3O2)2(C7H6N2S)2], the Zn atom is four-coordinated in the ZnO2N2 form in a distorted tetrahedral geometry. The amino groups act as donors in N—H...O hydrogen bonds. Two intermolecular N—H...O hydrogen bonds interconnect the mol­ecules into a three-dimensional network. The planes of the acetate ligands are nearly orthogonal, and the Zn atom is displaced slightly from these two planes.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802021864/na6189sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802021864/na6189Isup2.hkl
Contains datablock I

CCDC reference: 202978

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.024
  • wR factor = 0.060
  • Data-to-parameter ratio = 14.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes

REFLT_03 From the CIF: _diffrn_reflns_theta_max 28.29 From the CIF: _reflns_number_total 3811 Count of symmetry unique reflns 2815 Completeness (_total/calc) 135.38% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 996 Fraction of Friedel pairs measured 0.354 Are heavy atom types Z>Si present yes WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

Diacetatobis(2-aminobenzothiazolato)zinc(II) top
Crystal data top
[Zn(C2H3O2)2(C7H6N2S)2]Dx = 1.509 Mg m3
Mr = 483.89Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21Cell parameters from 7544 reflections
a = 8.5471 (7) Åθ = 2.4–28.3°
b = 27.547 (2) ŵ = 1.38 mm1
c = 9.0485 (8) ÅT = 293 K
V = 2130.4 (3) Å3Block, colorless
Z = 40.40 × 0.36 × 0.32 mm
F(000) = 992
Data collection top
Siemens SMART CCD area-detector
diffractometer
3811 independent reflections
Radiation source: fine-focus sealed tube3423 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
Detector resolution: 8.33 pixels mm-1θmax = 28.3°, θmin = 2.4°
ω scansh = 1111
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
k = 3633
Tmin = 0.608, Tmax = 0.666l = 712
12903 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.024H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.060 w = 1/[σ2(Fo2) + (0.033P)2 + 0.1054P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
3811 reflectionsΔρmax = 0.19 e Å3
264 parametersΔρmin = 0.23 e Å3
1 restraintAbsolute structure: (Flack, 1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.017 (9)
Special details top

Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different φ angle (0, 88 and 180°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 5 cm and the detector swing angle was -35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible.

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
Zn10.86524 (3)0.620875 (7)0.66460 (4)0.03651 (7)
S10.73336 (10)0.76943 (3)0.48023 (10)0.0686 (2)
S20.78644 (10)0.47845 (2)0.41383 (9)0.0619 (2)
O10.72280 (18)0.62668 (5)0.8334 (2)0.0406 (4)
O20.8581 (2)0.56659 (7)0.9255 (3)0.0707 (7)
O31.09278 (18)0.61168 (5)0.6828 (3)0.0455 (4)
O41.0691 (2)0.68250 (6)0.7921 (2)0.0496 (4)
N10.8126 (2)0.68116 (7)0.5448 (2)0.0394 (4)
N20.6896 (3)0.72383 (8)0.7361 (3)0.0563 (6)
H2A0.69500.69960.79580.068*
H2B0.64760.75060.76460.068*
N30.7956 (2)0.56299 (6)0.5405 (2)0.0407 (5)
N41.0252 (3)0.51751 (8)0.5601 (4)0.0662 (7)
H4A1.07170.53980.61000.079*
H4B1.07350.49100.53950.079*
C10.7461 (3)0.71995 (8)0.6004 (3)0.0409 (5)
C20.8263 (4)0.73522 (12)0.3456 (3)0.0609 (7)
C30.8666 (5)0.74944 (19)0.2023 (5)0.0977 (14)
H3A0.84260.78020.16670.117*
C40.9436 (6)0.71578 (19)0.1160 (5)0.1009 (14)
H4C0.97130.72390.01970.121*
C50.9801 (4)0.67038 (15)0.1692 (5)0.0834 (10)
H5A1.03300.64870.10830.100*
C60.9406 (4)0.65612 (12)0.3108 (3)0.0624 (8)
H6A0.96670.62540.34550.075*
C70.8606 (3)0.68893 (10)0.3997 (3)0.0454 (6)
C80.8807 (3)0.52397 (8)0.5154 (3)0.0457 (6)
C90.6199 (3)0.51519 (10)0.4028 (3)0.0528 (7)
C100.4801 (4)0.50537 (13)0.3327 (4)0.0687 (9)
H10A0.46450.47620.28320.082*
C110.3642 (4)0.54019 (17)0.3381 (4)0.0790 (11)
H11A0.26800.53420.29360.095*
C120.3901 (3)0.58407 (15)0.4096 (5)0.0740 (10)
H12A0.31130.60740.41080.089*
C130.5304 (3)0.59377 (11)0.4789 (4)0.0577 (7)
H13A0.54640.62330.52620.069*
C140.6470 (3)0.55886 (9)0.4769 (3)0.0441 (6)
C150.7522 (3)0.59636 (8)0.9361 (3)0.0429 (6)
C160.6487 (4)0.59846 (15)1.0702 (4)0.0742 (10)
H16A0.70440.58601.15420.111*
H16B0.55670.57921.05350.111*
H16C0.61900.63151.08870.111*
C171.1488 (3)0.64735 (8)0.7562 (3)0.0384 (5)
C181.3175 (3)0.64447 (12)0.8023 (4)0.0651 (8)
H18A1.37200.67280.76810.098*
H18B1.36430.61600.76010.098*
H18C1.32380.64280.90810.098*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.04038 (12)0.02557 (10)0.04358 (13)0.00296 (9)0.00364 (15)0.00700 (12)
S10.0949 (5)0.0515 (4)0.0592 (4)0.0246 (4)0.0129 (4)0.0249 (3)
S20.0833 (5)0.0362 (3)0.0661 (5)0.0105 (3)0.0047 (4)0.0229 (3)
O10.0469 (9)0.0332 (8)0.0416 (9)0.0070 (7)0.0062 (8)0.0053 (7)
O20.0645 (12)0.0489 (11)0.0986 (19)0.0175 (9)0.0057 (12)0.0290 (12)
O30.0422 (7)0.0307 (7)0.0636 (13)0.0009 (6)0.0040 (11)0.0086 (9)
O40.0550 (10)0.0374 (9)0.0566 (11)0.0052 (8)0.0099 (9)0.0109 (8)
N10.0466 (10)0.0339 (9)0.0378 (11)0.0013 (8)0.0019 (9)0.0021 (8)
N20.0886 (17)0.0306 (10)0.0497 (13)0.0218 (11)0.0211 (14)0.0071 (9)
N30.0447 (11)0.0320 (9)0.0455 (12)0.0027 (8)0.0058 (9)0.0121 (8)
N40.0630 (15)0.0399 (12)0.096 (2)0.0136 (10)0.0065 (14)0.0284 (13)
C10.0475 (13)0.0329 (11)0.0422 (13)0.0078 (10)0.0039 (11)0.0036 (9)
C20.0729 (17)0.0668 (19)0.0429 (16)0.0048 (15)0.0026 (14)0.0132 (13)
C30.125 (3)0.112 (3)0.056 (3)0.007 (3)0.017 (2)0.028 (2)
C40.124 (3)0.131 (4)0.047 (2)0.025 (3)0.025 (2)0.002 (2)
C50.091 (2)0.106 (3)0.0536 (17)0.023 (2)0.023 (2)0.026 (2)
C60.0678 (18)0.0644 (18)0.0550 (18)0.0151 (15)0.0127 (15)0.0214 (14)
C70.0467 (13)0.0551 (15)0.0345 (13)0.0069 (11)0.0002 (11)0.0042 (11)
C80.0590 (15)0.0305 (11)0.0476 (14)0.0018 (10)0.0079 (12)0.0135 (10)
C90.0643 (16)0.0498 (14)0.0443 (14)0.0196 (12)0.0102 (13)0.0098 (12)
C100.076 (2)0.076 (2)0.0539 (18)0.0328 (17)0.0007 (16)0.0145 (16)
C110.0587 (18)0.115 (3)0.063 (2)0.030 (2)0.0039 (16)0.008 (2)
C120.0473 (15)0.098 (3)0.076 (2)0.0015 (16)0.0017 (16)0.008 (2)
C130.0465 (13)0.0625 (17)0.0641 (18)0.0043 (12)0.0045 (14)0.0134 (14)
C140.0476 (13)0.0446 (13)0.0400 (13)0.0101 (10)0.0087 (11)0.0061 (10)
C150.0446 (12)0.0368 (11)0.0472 (15)0.0074 (10)0.0015 (11)0.0090 (10)
C160.074 (2)0.096 (3)0.0516 (19)0.0057 (18)0.0084 (16)0.0208 (19)
C170.0407 (11)0.0365 (12)0.0381 (12)0.0111 (10)0.0072 (10)0.0054 (9)
C180.0482 (14)0.0632 (19)0.084 (2)0.0071 (13)0.0082 (16)0.0008 (17)
Geometric parameters (Å, º) top
Zn1—O11.960 (2)C3—H3A0.9300
Zn1—O31.968 (2)C4—C51.376 (6)
Zn1—N12.034 (2)C4—H4C0.9300
Zn1—N32.039 (2)C5—C61.381 (6)
S1—C21.733 (3)C5—H5A0.9300
S1—C11.747 (2)C6—C71.390 (4)
S2—C91.749 (3)C6—H6A0.9300
S2—C81.751 (2)C9—C101.380 (4)
O1—C151.274 (3)C9—C141.396 (4)
O2—C151.225 (3)C10—C111.380 (5)
O3—C171.279 (3)C10—H10A0.9300
O4—C171.228 (3)C11—C121.389 (5)
N1—C11.311 (3)C11—H11A0.9300
N1—C71.391 (3)C12—C131.379 (4)
N2—C11.324 (3)C12—H12A0.9300
N2—H2A0.8600C13—C141.385 (4)
N2—H2B0.8600C13—H13A0.9300
N3—C81.317 (3)C15—C161.503 (4)
N3—C141.399 (3)C16—H16A0.9600
N4—C81.312 (3)C16—H16B0.9600
N4—H4A0.8600C16—H16C0.9600
N4—H4B0.8600C17—C181.502 (4)
C2—C71.397 (4)C18—H18A0.9600
C2—C31.398 (5)C18—H18B0.9600
C3—C41.379 (6)C18—H18C0.9600
O1—Zn1—O3124.00 (9)C6—C7—C2119.6 (3)
O1—Zn1—N1102.21 (7)N1—C7—C2114.1 (2)
O3—Zn1—N1111.62 (8)N4—C8—N3125.3 (2)
O1—Zn1—N3108.15 (8)N4—C8—S2119.84 (18)
O3—Zn1—N3103.53 (8)N3—C8—S2114.87 (19)
N1—Zn1—N3106.27 (9)C10—C9—C14122.2 (3)
C2—S1—C189.12 (13)C10—C9—S2128.1 (2)
C9—S2—C889.41 (12)C14—C9—S2109.7 (2)
C15—O1—Zn1113.09 (14)C9—C10—C11118.0 (3)
C17—O3—Zn1108.34 (14)C9—C10—H10A121.0
C1—N1—C7111.4 (2)C11—C10—H10A121.0
C1—N1—Zn1123.83 (17)C10—C11—C12120.5 (3)
C7—N1—Zn1124.27 (16)C10—C11—H11A119.8
C1—N2—H2A120.0C12—C11—H11A119.8
C1—N2—H2B120.0C13—C12—C11121.3 (3)
H2A—N2—H2B120.0C13—C12—H12A119.4
C8—N3—C14111.4 (2)C11—C12—H12A119.4
C8—N3—Zn1124.85 (17)C12—C13—C14119.0 (3)
C14—N3—Zn1123.72 (15)C12—C13—H13A120.5
C8—N4—H4A120.0C14—C13—H13A120.5
C8—N4—H4B120.0C13—C14—C9119.0 (2)
H4A—N4—H4B120.0C13—C14—N3126.3 (2)
N1—C1—N2125.5 (2)C9—C14—N3114.7 (2)
N1—C1—S1115.08 (19)O2—C15—O1121.8 (2)
N2—C1—S1119.44 (18)O2—C15—C16121.6 (3)
C7—C2—C3121.9 (3)O1—C15—C16116.6 (2)
C7—C2—S1110.3 (2)C15—C16—H16A109.5
C3—C2—S1127.8 (3)C15—C16—H16B109.5
C4—C3—C2117.0 (4)H16A—C16—H16B109.5
C4—C3—H3A121.5C15—C16—H16C109.5
C2—C3—H3A121.5H16A—C16—H16C109.5
C5—C4—C3121.4 (4)H16B—C16—H16C109.5
C5—C4—H4C119.3O4—C17—O3122.3 (2)
C3—C4—H4C119.3O4—C17—C18120.1 (2)
C4—C5—C6121.8 (4)O3—C17—C18117.6 (2)
C4—C5—H5A119.1C17—C18—H18A109.5
C6—C5—H5A119.1C17—C18—H18B109.5
C5—C6—C7118.2 (3)H18A—C18—H18B109.5
C5—C6—H6A120.9C17—C18—H18C109.5
C7—C6—H6A120.9H18A—C18—H18C109.5
C6—C7—N1126.2 (3)H18B—C18—H18C109.5
O3—Zn1—O1—C1542.79 (18)Zn1—N1—C7—C65.1 (3)
N1—Zn1—O1—C15169.71 (16)C1—N1—C7—C20.8 (3)
N3—Zn1—O1—C1578.41 (17)Zn1—N1—C7—C2172.88 (19)
O1—Zn1—O3—C1758.55 (19)C3—C2—C7—C61.6 (5)
N1—Zn1—O3—C1764.2 (2)S1—C2—C7—C6177.7 (2)
N3—Zn1—O3—C17178.16 (17)C3—C2—C7—N1179.8 (3)
O1—Zn1—N1—C122.0 (2)S1—C2—C7—N10.4 (3)
O3—Zn1—N1—C1112.5 (2)C14—N3—C8—N4179.3 (3)
N3—Zn1—N1—C1135.3 (2)Zn1—N3—C8—N43.6 (4)
O1—Zn1—N1—C7166.90 (18)C14—N3—C8—S20.7 (3)
O3—Zn1—N1—C758.6 (2)Zn1—N3—C8—S2176.41 (12)
N3—Zn1—N1—C753.6 (2)C9—S2—C8—N4179.4 (3)
O1—Zn1—N3—C8118.0 (2)C9—S2—C8—N30.6 (2)
O3—Zn1—N3—C815.2 (2)C8—S2—C9—C10179.0 (3)
N1—Zn1—N3—C8132.9 (2)C8—S2—C9—C140.3 (2)
O1—Zn1—N3—C1458.8 (2)C14—C9—C10—C110.5 (5)
O3—Zn1—N3—C14168.1 (2)S2—C9—C10—C11179.8 (3)
N1—Zn1—N3—C1450.3 (2)C9—C10—C11—C121.4 (6)
C7—N1—C1—N2179.5 (3)C10—C11—C12—C131.1 (6)
Zn1—N1—C1—N27.4 (4)C11—C12—C13—C140.2 (6)
C7—N1—C1—S10.9 (3)C12—C13—C14—C91.0 (5)
Zn1—N1—C1—S1172.98 (11)C12—C13—C14—N3179.5 (3)
C2—S1—C1—N10.6 (2)C10—C9—C14—C130.7 (5)
C2—S1—C1—N2179.8 (3)S2—C9—C14—C13178.7 (2)
C1—S1—C2—C70.1 (2)C10—C9—C14—N3179.4 (3)
C1—S1—C2—C3179.2 (4)S2—C9—C14—N30.0 (3)
C7—C2—C3—C40.6 (6)C8—N3—C14—C13178.1 (3)
S1—C2—C3—C4178.7 (3)Zn1—N3—C14—C134.7 (4)
C2—C3—C4—C50.5 (7)C8—N3—C14—C90.4 (3)
C3—C4—C5—C60.6 (7)Zn1—N3—C14—C9176.69 (19)
C4—C5—C6—C70.5 (5)Zn1—O1—C15—O21.1 (3)
C5—C6—C7—N1179.4 (3)Zn1—O1—C15—C16179.7 (2)
C5—C6—C7—C21.6 (4)Zn1—O3—C17—O46.7 (3)
C1—N1—C7—C6177.2 (3)Zn1—O3—C17—C18171.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O10.862.052.832 (3)151
N2—H2B···O4i0.861.982.824 (3)168
N4—H4A···O30.862.102.880 (3)152
N4—H4B···O2ii0.861.982.801 (3)159
Symmetry codes: (i) x1/2, y+3/2, z; (ii) x+2, y+1, z1/2.
 

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