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
CCDC reference: 258635
Key indicators
- Single-crystal X-ray study
- T = 102 K
- Mean (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
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.
Crystal data top
[Zn(C2H3O2)2(C12H13N3)]·2C2H4O2 | F(000) = 1048.00 |
Mr = 502.83 | Dx = 1.421 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.7107 Å |
Hall symbol: -C 2yc | Cell parameters from 3432 reflections |
a = 8.703 (2) Å | θ = 2.5–30.5° |
b = 13.791 (3) Å | µ = 1.09 mm−1 |
c = 19.623 (4) Å | T = 102 K |
β = 93.80 (2)° | Fragment, colorless |
V = 2350.0 (8) Å3 | 0.43 × 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 tube | 2597 reflections with I > 3.00σ(I) |
Graphite monochromator | Rint = 0.020 |
ω scans with κ offsets | θmax = 30.5°, θmin = 2.8° |
Absorption correction: multi-scan (HKL SCALEPACK; Otwinowski & Minor, 1997) | h = −12→12 |
Tmin = 0.631, Tmax = 0.667 | k = −19→19 |
6634 measured reflections | l = −27→27 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | 0 constraints |
R[F2 > 2σ(F2)] = 0.073 | H-atom parameters not refined |
wR(F2) = 0.150 | Weighting scheme based on measured s.u.'s w = 1/[σ2(Fo) + 0.004225|Fo|2] |
S = 0.99 | (Δ/σ)max = 0.000277 |
2597 reflections | Δρmax = 1.36 e Å−3 |
150 parameters | Δρmin = −0.44 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
Zn1 | 0.0000 | 0.20056 (3) | 0.7500 | 0.03077 (12) | |
O1 | 0.0581 (2) | 0.29837 (11) | 0.67964 (9) | 0.0359 (5) | |
O2 | 0.1024 (3) | 0.1643 (2) | 0.62473 (12) | 0.0585 (7) | |
O3 | 0.1716 (3) | 0.0495 (2) | 0.52865 (11) | 0.0530 (6) | |
O4 | 0.1311 (4) | −0.0602 (2) | 0.6047 (1) | 0.0902 (11) | |
N1 | −0.2223 (3) | 0.1672 (2) | 0.70436 (10) | 0.0319 (5) | |
N2 | 0.0161 (6) | 0.0460 (3) | 0.7337 (2) | 0.0349 (12) | 0.500 |
C1 | −0.3273 (3) | 0.2331 (2) | 0.6815 (1) | 0.0399 (7) | |
C2 | −0.4732 (4) | 0.2075 (2) | 0.6562 (2) | 0.0469 (8) | |
C3 | −0.5120 (4) | 0.1102 (2) | 0.6548 (2) | 0.0491 (8) | |
C4 | −0.4042 (4) | 0.0427 (2) | 0.6777 (2) | 0.0441 (7) | |
C5 | −0.2594 (3) | 0.0737 (2) | 0.70155 (12) | 0.0357 (6) | |
C6 | −0.1340 (4) | 0.0036 (2) | 0.7262 (2) | 0.0491 (8) | |
C7 | 0.0936 (3) | 0.2559 (2) | 0.6266 (1) | 0.0405 (7) | |
C8 | 0.1267 (5) | 0.3157 (3) | 0.5657 (2) | 0.0612 (11) | |
C9 | 0.1634 (4) | −0.0409 (3) | 0.5484 (2) | 0.0513 (8) | |
C10 | 0.2092 (5) | −0.1087 (3) | 0.4950 (3) | 0.086 (2) | |
H1 | −0.3000 | 0.2998 | 0.6828 | 0.048* | |
H2 | −0.5452 | 0.2554 | 0.6401 | 0.056* | |
H3 | −0.6121 | 0.0902 | 0.6383 | 0.059* | |
H4 | −0.4289 | −0.0244 | 0.6771 | 0.053* | |
H5 | −0.1315 | −0.0479 | 0.6942 | 0.059* | |
H6 | −0.1586 | −0.0213 | 0.7692 | 0.059* | |
H7 | 0.1726 | 0.3757 | 0.5804 | 0.037* | 0.500 |
H8 | 0.1936 | 0.2822 | 0.5381 | 0.037* | 0.500 |
H9 | 0.0321 | 0.3294 | 0.5398 | 0.037* | 0.500 |
H10 | 0.1848 | −0.0812 | 0.4513 | 0.103* | |
H11 | 0.1555 | −0.1682 | 0.4988 | 0.103* | |
H12 | 0.3170 | −0.1202 | 0.5007 | 0.103* | |
H13 | 0.1399 | 0.0939 | 0.5674 | 0.064* | |
H14 | 0.0473 | 0.0402 | 0.6863 | 0.042* | 0.500 |
H15 | 0.0890 | 0.3515 | 0.5628 | 0.037* | 0.500 |
H16 | 0.2455 | 0.3388 | 0.5696 | 0.037* | 0.500 |
H17 | 0.0946 | 0.2793 | 0.5181 | 0.037* | 0.500 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Zn1 | 0.0421 (3) | 0.0169 (2) | 0.0339 (2) | 0.0000 | 0.0064 (2) | 0.0000 |
O1 | 0.0488 (11) | 0.0240 (8) | 0.0356 (9) | −0.0015 (7) | 0.0087 (8) | 0.0029 (6) |
O2 | 0.066 (2) | 0.0448 (13) | 0.065 (1) | 0.0079 (11) | 0.0048 (11) | −0.0223 (12) |
O3 | 0.0611 (13) | 0.051 (1) | 0.0485 (11) | −0.0052 (11) | 0.0174 (9) | −0.0078 (10) |
O4 | 0.156 (3) | 0.059 (2) | 0.056 (2) | 0.023 (2) | 0.005 (2) | 0.0211 (13) |
N1 | 0.0426 (12) | 0.0225 (9) | 0.0315 (9) | −0.0016 (8) | 0.0087 (8) | −0.0016 (7) |
N2 | 0.045 (3) | 0.021 (2) | 0.040 (3) | 0.003 (2) | 0.012 (2) | 0.004 (1) |
C1 | 0.050 (2) | 0.0286 (11) | 0.0414 (13) | −0.0006 (11) | 0.0057 (11) | −0.0013 (11) |
C2 | 0.050 (2) | 0.042 (2) | 0.048 (2) | 0.0062 (12) | −0.0001 (12) | −0.0023 (12) |
C3 | 0.045 (2) | 0.055 (2) | 0.048 (2) | −0.0070 (13) | 0.0038 (11) | −0.0071 (13) |
C4 | 0.053 (2) | 0.0340 (13) | 0.046 (1) | −0.0093 (12) | 0.0100 (12) | −0.0072 (11) |
C5 | 0.049 (1) | 0.0267 (11) | 0.0334 (11) | −0.0041 (10) | 0.0137 (10) | −0.0036 (9) |
C6 | 0.056 (2) | 0.0202 (11) | 0.071 (2) | −0.0021 (11) | 0.003 (1) | 0.0003 (12) |
C7 | 0.041 (1) | 0.037 (2) | 0.0438 (13) | −0.0003 (11) | 0.0071 (10) | −0.0047 (11) |
C8 | 0.074 (2) | 0.071 (3) | 0.040 (2) | 0.001 (2) | 0.018 (2) | 0.001 (1) |
C9 | 0.052 (2) | 0.056 (2) | 0.044 (2) | 0.027 (1) | −0.0066 (12) | −0.0041 (13) |
C10 | 0.073 (3) | 0.082 (3) | 0.100 (3) | 0.038 (2) | −0.006 (2) | −0.043 (3) |
Geometric parameters (Å, º) top
Zn1—O1 | 2.019 (2) | C7—C8 | 1.495 (4) |
Zn1—O1i | 2.019 (2) | C9—C10 | 1.478 (5) |
Zn1—N1 | 2.128 (2) | O3—H13 | 1.029 |
Zn1—N1i | 2.128 (2) | N2—H14 | 0.990 |
Zn1—N2 | 2.161 (4) | C1—H1 | 0.950 |
Zn1—N2i | 2.161 (4) | C2—H2 | 0.950 |
O1—C7 | 1.251 (3) | C3—H3 | 0.950 |
O2—C7 | 1.267 (4) | C4—H4 | 0.950 |
O3—C9 | 1.310 (4) | C6—H5 | 0.950 |
O4—C9 | 1.188 (4) | C6—H6 | 0.950 |
N1—C1 | 1.344 (4) | C8—H7 | 0.955 |
N1—C5 | 1.330 (3) | C8—H8 | 0.943 |
N2—N2i | 0.713 (7) | C8—H9 | 0.957 |
N2—C6 | 1.429 (6) | C8—H15 | 0.594 |
N2—C6i | 1.381 (6) | C8—H16 | 1.080 |
C1—C2 | 1.378 (5) | C8—H17 | 1.081 |
C2—C3 | 1.383 (4) | C10—H10 | 0.950 |
C3—C4 | 1.376 (5) | C10—H11 | 0.949 |
C4—C5 | 1.383 (4) | C10—H12 | 0.951 |
C5—C6 | 1.513 (4) | | |
| | | |
O1···C4ii | 3.385 (3) | O3···O4iv | 3.591 (4) |
O2···O3 | 2.563 (3) | O4···N2 | 3.146 (5) |
O2···O4 | 3.132 (4) | O4···C1vi | 3.234 (4) |
O2···C9 | 3.262 (4) | O4···C6i | 3.432 (4) |
O2···C3iii | 3.450 (4) | O4···C2vi | 3.498 (4) |
O2···C10iv | 3.553 (5) | O4···C6 | 3.537 (5) |
O3···C9iv | 3.196 (4) | C3···C4vii | 3.538 (4) |
O3···C8v | 3.225 (4) | C3···C5vii | 3.591 (4) |
O3···O3iv | 3.406 (5) | C4···C4vii | 3.386 (6) |
O3···C10iv | 3.415 (5) | C9···C9iv | 3.501 (6) |
O3···C7 | 3.526 (3) | | |
| | | |
O1—Zn1—O1i | 96.1 (1) | C4—C3—H3 | 120.35 |
O1—Zn1—N1 | 96.81 (8) | C3—C4—H4 | 120.40 |
O1—Zn1—N1i | 99.80 (8) | C5—C4—H4 | 120.42 |
O1—Zn1—N2 | 122.5 (1) | N2—C6—H5 | 108.30 |
O1—Zn1—N2i | 141.4 (1) | N2—C6—H6 | 108.30 |
N1—Zn1—N1i | 155.1 (1) | C5—C6—H5 | 108.35 |
N1—Zn1—N2 | 77.9 (2) | C5—C6—H6 | 108.35 |
N1—Zn1—N2i | 77.5 (2) | H5—C6—H6 | 109.47 |
Zn1—O1—C7 | 110.1 (2) | C7—C8—H7 | 109.57 |
Zn1—N1—C1 | 125.0 (2) | C7—C8—H8 | 110.37 |
Zn1—N1—C5 | 116.0 (2) | C7—C8—H9 | 109.26 |
C1—N1—C5 | 118.9 (2) | C7—C8—H15 | 113.69 |
Zn1—N2—C6 | 110.5 (3) | C7—C8—H16 | 109.88 |
N1—C1—C2 | 122.5 (3) | C7—C8—H17 | 112.49 |
C1—C2—C3 | 118.3 (3) | H7—C8—H8 | 109.66 |
C2—C3—C4 | 119.3 (3) | H7—C8—H9 | 108.46 |
C3—C4—C5 | 119.2 (3) | H7—C8—H15 | 61.70 |
N1—C5—C4 | 121.8 (3) | H7—C8—H16 | 48.97 |
N1—C5—C6 | 116.0 (2) | H7—C8—H17 | 137.92 |
C4—C5—C6 | 122.2 (2) | H8—C8—H9 | 109.48 |
N2—C6—C5 | 114.0 (3) | H8—C8—H15 | 135.31 |
O1—C7—O2 | 120.6 (3) | H8—C8—H16 | 63.90 |
O1—C7—C8 | 118.6 (3) | H8—C8—H17 | 53.79 |
O2—C7—C8 | 120.8 (3) | H9—C8—H15 | 48.22 |
O3—C9—O4 | 120.6 (3) | H9—C8—H16 | 139.87 |
O3—C9—C10 | 111.8 (3) | H9—C8—H17 | 57.91 |
O4—C9—C10 | 127.5 (4) | H15—C8—H16 | 106.37 |
C9—O3—H13 | 109.01 | H15—C8—H17 | 101.14 |
Zn1—N2—H14 | 104.06 | H16—C8—H17 | 112.92 |
C6—N2—H14 | 100.10 | C9—C10—H10 | 109.45 |
N1—C1—H1 | 118.76 | C9—C10—H11 | 109.50 |
C2—C1—H1 | 118.75 | C9—C10—H12 | 109.42 |
C1—C2—H2 | 120.86 | H10—C10—H11 | 109.54 |
C3—C2—H2 | 120.88 | H10—C10—H12 | 109.43 |
C2—C3—H3 | 120.34 | H11—C10—H12 | 109.49 |
| | | |
Zn1—O1—C7—O2 | −6.0 (3) | N1—Zn1—N2—C6 | −20.5 (3) |
Zn1—O1—C7—C8 | 174.5 (2) | N1—C1—C2—C3 | 0.3 (5) |
Zn1—O1—C7—O2 | −6.0 (3) | N1—C5—C4—C3 | 1.4 (4) |
Zn1—N1—C1—C2 | −175.9 (2) | N1—C5—C6—N2 | −14.0 (4) |
Zn1—N1—C5—C4 | 175.3 (2) | N2—Zn1—O1—C7 | 3.9 (3) |
Zn1—N1—C5—C6 | −4.6 (3) | N2—Zn1—O1i—C7i | 2.4 (3) |
Zn1—N2—C6—C5 | 24.6 (4) | N2—Zn1—N1—C1 | −169.0 (2) |
O1—Zn1—O1i—C7i | −176.7 (2) | N2—Zn1—N1—C5 | 13.9 (2) |
O1—Zn1—N1—C1 | −47.2 (2) | N2—Zn1—N1i—C1i | 171.5 (2) |
O1—Zn1—N1—C5 | 135.7 (2) | N2—Zn1—N1i—C5i | −5.5 (2) |
O1—Zn1—N1i—C1i | 50.2 (2) | N2—C6—C5—C4 | 166.2 (3) |
O1—Zn1—N1i—C5i | −126.8 (2) | C1—N1—C5—C4 | −1.9 (4) |
O1—Zn1—N2—C6 | −110.9 (2) | C1—N1—C5—C6 | 178.2 (2) |
N1—Zn1—O1—C7 | −76.1 (2) | C1—C2—C3—C4 | −0.9 (5) |
N1—Zn1—O1i—C7i | 85.2 (2) | C2—C1—N1—C5 | 1.1 (4) |
N1—Zn1—N1i—C1i | −178.8 (2) | C2—C3—C4—C5 | 0.1 (4) |
N1—Zn1—N1i—C5i | 4.2 (2) | C3—C4—C5—C6 | −178.8 (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, y−1/2, z; (vii) −x−1, y, −z+3/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H14···O2 | 0.99 | 2.16 | 2.831 (5) | 123 |
N2—H14···O4 | 0.99 | 2.27 | 3.146 (5) | 146 |
O3—H13···O2 | 1.03 | 1.54 | 2.563 (3) | 176 |