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The title compound, [Zn(C2H3O2)2(C12H13N3)]·2C2H4O2, consists of a five-coordinate trigonal–bipyramidal zinc complex (one N,N′,N′′-tridentate donor and two O-monodentate donors) and two acetic acid mol­ecules. The acetic acid mol­ecules hydrogen bond with the coordination complex. The coordination complex is located on a twofold axis that passes through the Zn atom and the secondary amine N atom is disordered across that axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804027618/fl6131sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804027618/fl6131Isup2.hkl
Contains datablock I

CCDC reference: 258635

Key indicators

  • Single-crystal X-ray study
  • T = 102 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.073
  • wR factor = 0.150
  • Data-to-parameter ratio = 17.3

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT413_ALERT_2_B Short Inter XH3 .. XHn H9 .. H12 .. 2.09 Ang.
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 3.09 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors for C9 PLAT301_ALERT_3_C Main Residue Disorder ......................... 4.00 Perc. PLAT355_ALERT_3_C Long O-H Bond (0.82A) O3 - H13 ... 1.03 Ang.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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

Computing details top

Data collection: COLLECT (Nonius 2000); cell refinement: DENZO and SCALEPACK; data reduction: DENZO and SCALEPACK (Version 1.96.2; Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare, et al. 1993); program(s) used to refine structure: TEXSAN for Windows (Molecular Structure Corporation, 1997-1999); molecular graphics: TEXSAN for Windows; software used to prepare material for publication: TEXSAN for Windows.

(I) top
Crystal data top
[Zn(C2H3O2)2(C12H13N3)]·2C2H4O2F(000) = 1048.00
Mr = 502.83Dx = 1.421 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.7107 Å
Hall symbol: -C 2ycCell parameters from 3432 reflections
a = 8.703 (2) Åθ = 2.5–30.5°
b = 13.791 (3) ŵ = 1.09 mm1
c = 19.623 (4) ÅT = 102 K
β = 93.80 (2)°Fragment, colorless
V = 2350.0 (8) Å30.43 × 0.42 × 0.37 mm
Z = 4
Data collection top
KappaCCD (with Oxford Cryosystems Cryostream coller)
diffractometer
3572 independent reflections
Radiation source: fine-focus sealed tube2597 reflections with I > 3.00σ(I)
Graphite monochromatorRint = 0.020
ω scans with κ offsetsθmax = 30.5°, θmin = 2.8°
Absorption correction: multi-scan
(HKL SCALEPACK; Otwinowski & Minor, 1997)
h = 1212
Tmin = 0.631, Tmax = 0.667k = 1919
6634 measured reflectionsl = 2727
Refinement top
Refinement on F20 restraints
Least-squares matrix: full0 constraints
R[F2 > 2σ(F2)] = 0.073H-atom parameters not refined
wR(F2) = 0.150Weighting scheme based on measured s.u.'s w = 1/[σ2(Fo) + 0.004225|Fo|2]
S = 0.99(Δ/σ)max = 0.000277
2597 reflectionsΔρmax = 1.36 e Å3
150 parametersΔρmin = 0.44 e Å3
Special details top

Geometry. Zn1 is located on the 2-fold axis, and N2 is disordered about, but not on, the 2-fold axis. H13 and H14, the hydrogen atoms associated with O3 and N2, respectively, were found in difference maps, but not refined. The methyl group of the acetato ligand is disordered. The first set of hydrogen atoms (H7, H8 & H9) were placed in calculated positions. The second set (H15, H16 & H17) were found in difference maps, but not refined. These 6 hydrogen atoms have half occupancies.

Refinement. Refinement of F2. The weighted R-factor wR and goodness of fit are based on F2, conventional R-factors R are based on F. R-factors based on F2 are statistically about twice as large as those based on F. H13 and H14, the hydrogen atoms associated with O3 and N2, respectively, were found in difference maps, but not refined. All of the hydrogen atoms are assigned thermal parameters 1.2 times larger than the atoms to which they are bound.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Zn10.00000.20056 (3)0.75000.03077 (12)
O10.0581 (2)0.29837 (11)0.67964 (9)0.0359 (5)
O20.1024 (3)0.1643 (2)0.62473 (12)0.0585 (7)
O30.1716 (3)0.0495 (2)0.52865 (11)0.0530 (6)
O40.1311 (4)0.0602 (2)0.6047 (1)0.0902 (11)
N10.2223 (3)0.1672 (2)0.70436 (10)0.0319 (5)
N20.0161 (6)0.0460 (3)0.7337 (2)0.0349 (12)0.500
C10.3273 (3)0.2331 (2)0.6815 (1)0.0399 (7)
C20.4732 (4)0.2075 (2)0.6562 (2)0.0469 (8)
C30.5120 (4)0.1102 (2)0.6548 (2)0.0491 (8)
C40.4042 (4)0.0427 (2)0.6777 (2)0.0441 (7)
C50.2594 (3)0.0737 (2)0.70155 (12)0.0357 (6)
C60.1340 (4)0.0036 (2)0.7262 (2)0.0491 (8)
C70.0936 (3)0.2559 (2)0.6266 (1)0.0405 (7)
C80.1267 (5)0.3157 (3)0.5657 (2)0.0612 (11)
C90.1634 (4)0.0409 (3)0.5484 (2)0.0513 (8)
C100.2092 (5)0.1087 (3)0.4950 (3)0.086 (2)
H10.30000.29980.68280.048*
H20.54520.25540.64010.056*
H30.61210.09020.63830.059*
H40.42890.02440.67710.053*
H50.13150.04790.69420.059*
H60.15860.02130.76920.059*
H70.17260.37570.58040.037*0.500
H80.19360.28220.53810.037*0.500
H90.03210.32940.53980.037*0.500
H100.18480.08120.45130.103*
H110.15550.16820.49880.103*
H120.31700.12020.50070.103*
H130.13990.09390.56740.064*
H140.04730.04020.68630.042*0.500
H150.08900.35150.56280.037*0.500
H160.24550.33880.56960.037*0.500
H170.09460.27930.51810.037*0.500
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0421 (3)0.0169 (2)0.0339 (2)0.00000.0064 (2)0.0000
O10.0488 (11)0.0240 (8)0.0356 (9)0.0015 (7)0.0087 (8)0.0029 (6)
O20.066 (2)0.0448 (13)0.065 (1)0.0079 (11)0.0048 (11)0.0223 (12)
O30.0611 (13)0.051 (1)0.0485 (11)0.0052 (11)0.0174 (9)0.0078 (10)
O40.156 (3)0.059 (2)0.056 (2)0.023 (2)0.005 (2)0.0211 (13)
N10.0426 (12)0.0225 (9)0.0315 (9)0.0016 (8)0.0087 (8)0.0016 (7)
N20.045 (3)0.021 (2)0.040 (3)0.003 (2)0.012 (2)0.004 (1)
C10.050 (2)0.0286 (11)0.0414 (13)0.0006 (11)0.0057 (11)0.0013 (11)
C20.050 (2)0.042 (2)0.048 (2)0.0062 (12)0.0001 (12)0.0023 (12)
C30.045 (2)0.055 (2)0.048 (2)0.0070 (13)0.0038 (11)0.0071 (13)
C40.053 (2)0.0340 (13)0.046 (1)0.0093 (12)0.0100 (12)0.0072 (11)
C50.049 (1)0.0267 (11)0.0334 (11)0.0041 (10)0.0137 (10)0.0036 (9)
C60.056 (2)0.0202 (11)0.071 (2)0.0021 (11)0.003 (1)0.0003 (12)
C70.041 (1)0.037 (2)0.0438 (13)0.0003 (11)0.0071 (10)0.0047 (11)
C80.074 (2)0.071 (3)0.040 (2)0.001 (2)0.018 (2)0.001 (1)
C90.052 (2)0.056 (2)0.044 (2)0.027 (1)0.0066 (12)0.0041 (13)
C100.073 (3)0.082 (3)0.100 (3)0.038 (2)0.006 (2)0.043 (3)
Geometric parameters (Å, º) top
Zn1—O12.019 (2)C7—C81.495 (4)
Zn1—O1i2.019 (2)C9—C101.478 (5)
Zn1—N12.128 (2)O3—H131.029
Zn1—N1i2.128 (2)N2—H140.990
Zn1—N22.161 (4)C1—H10.950
Zn1—N2i2.161 (4)C2—H20.950
O1—C71.251 (3)C3—H30.950
O2—C71.267 (4)C4—H40.950
O3—C91.310 (4)C6—H50.950
O4—C91.188 (4)C6—H60.950
N1—C11.344 (4)C8—H70.955
N1—C51.330 (3)C8—H80.943
N2—N2i0.713 (7)C8—H90.957
N2—C61.429 (6)C8—H150.594
N2—C6i1.381 (6)C8—H161.080
C1—C21.378 (5)C8—H171.081
C2—C31.383 (4)C10—H100.950
C3—C41.376 (5)C10—H110.949
C4—C51.383 (4)C10—H120.951
C5—C61.513 (4)
O1···C4ii3.385 (3)O3···O4iv3.591 (4)
O2···O32.563 (3)O4···N23.146 (5)
O2···O43.132 (4)O4···C1vi3.234 (4)
O2···C93.262 (4)O4···C6i3.432 (4)
O2···C3iii3.450 (4)O4···C2vi3.498 (4)
O2···C10iv3.553 (5)O4···C63.537 (5)
O3···C9iv3.196 (4)C3···C4vii3.538 (4)
O3···C8v3.225 (4)C3···C5vii3.591 (4)
O3···O3iv3.406 (5)C4···C4vii3.386 (6)
O3···C10iv3.415 (5)C9···C9iv3.501 (6)
O3···C73.526 (3)
O1—Zn1—O1i96.1 (1)C4—C3—H3120.35
O1—Zn1—N196.81 (8)C3—C4—H4120.40
O1—Zn1—N1i99.80 (8)C5—C4—H4120.42
O1—Zn1—N2122.5 (1)N2—C6—H5108.30
O1—Zn1—N2i141.4 (1)N2—C6—H6108.30
N1—Zn1—N1i155.1 (1)C5—C6—H5108.35
N1—Zn1—N277.9 (2)C5—C6—H6108.35
N1—Zn1—N2i77.5 (2)H5—C6—H6109.47
Zn1—O1—C7110.1 (2)C7—C8—H7109.57
Zn1—N1—C1125.0 (2)C7—C8—H8110.37
Zn1—N1—C5116.0 (2)C7—C8—H9109.26
C1—N1—C5118.9 (2)C7—C8—H15113.69
Zn1—N2—C6110.5 (3)C7—C8—H16109.88
N1—C1—C2122.5 (3)C7—C8—H17112.49
C1—C2—C3118.3 (3)H7—C8—H8109.66
C2—C3—C4119.3 (3)H7—C8—H9108.46
C3—C4—C5119.2 (3)H7—C8—H1561.70
N1—C5—C4121.8 (3)H7—C8—H1648.97
N1—C5—C6116.0 (2)H7—C8—H17137.92
C4—C5—C6122.2 (2)H8—C8—H9109.48
N2—C6—C5114.0 (3)H8—C8—H15135.31
O1—C7—O2120.6 (3)H8—C8—H1663.90
O1—C7—C8118.6 (3)H8—C8—H1753.79
O2—C7—C8120.8 (3)H9—C8—H1548.22
O3—C9—O4120.6 (3)H9—C8—H16139.87
O3—C9—C10111.8 (3)H9—C8—H1757.91
O4—C9—C10127.5 (4)H15—C8—H16106.37
C9—O3—H13109.01H15—C8—H17101.14
Zn1—N2—H14104.06H16—C8—H17112.92
C6—N2—H14100.10C9—C10—H10109.45
N1—C1—H1118.76C9—C10—H11109.50
C2—C1—H1118.75C9—C10—H12109.42
C1—C2—H2120.86H10—C10—H11109.54
C3—C2—H2120.88H10—C10—H12109.43
C2—C3—H3120.34H11—C10—H12109.49
Zn1—O1—C7—O26.0 (3)N1—Zn1—N2—C620.5 (3)
Zn1—O1—C7—C8174.5 (2)N1—C1—C2—C30.3 (5)
Zn1—O1—C7—O26.0 (3)N1—C5—C4—C31.4 (4)
Zn1—N1—C1—C2175.9 (2)N1—C5—C6—N214.0 (4)
Zn1—N1—C5—C4175.3 (2)N2—Zn1—O1—C73.9 (3)
Zn1—N1—C5—C64.6 (3)N2—Zn1—O1i—C7i2.4 (3)
Zn1—N2—C6—C524.6 (4)N2—Zn1—N1—C1169.0 (2)
O1—Zn1—O1i—C7i176.7 (2)N2—Zn1—N1—C513.9 (2)
O1—Zn1—N1—C147.2 (2)N2—Zn1—N1i—C1i171.5 (2)
O1—Zn1—N1—C5135.7 (2)N2—Zn1—N1i—C5i5.5 (2)
O1—Zn1—N1i—C1i50.2 (2)N2—C6—C5—C4166.2 (3)
O1—Zn1—N1i—C5i126.8 (2)C1—N1—C5—C41.9 (4)
O1—Zn1—N2—C6110.9 (2)C1—N1—C5—C6178.2 (2)
N1—Zn1—O1—C776.1 (2)C1—C2—C3—C40.9 (5)
N1—Zn1—O1i—C7i85.2 (2)C2—C1—N1—C51.1 (4)
N1—Zn1—N1i—C1i178.8 (2)C2—C3—C4—C50.1 (4)
N1—Zn1—N1i—C5i4.2 (2)C3—C4—C5—C6178.8 (3)
Symmetry codes: (i) x, y, z+3/2; (ii) x+1/2, y+1/2, z; (iii) x+1, y, z; (iv) x, y, z+1; (v) x+1/2, y+1/2, z+1; (vi) x+1/2, y1/2, z; (vii) x1, y, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H14···O20.992.162.831 (5)123
N2—H14···O40.992.273.146 (5)146
O3—H13···O21.031.542.563 (3)176
 

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