The structure of the title complex, [Zn
2(C
2H
3O
2)
4(C
11H
9N
3O)
2], is triclinic containing half of the molecule in the asymmetric unit. Each zinc atom is coordinated to a pyridyl and oxime nitrogen from one di-2-pyridyl ketone oxime (dpko) ligand and a third nitrogen from the other dpko pyridyl ring. Additionally, each zinc is coordinated to two acetato anions, one of which is bidentate and the other monodentate. The uncoordinated oxygen of the monodentate acetato group is involved in a hydrogen bond with the oxime hydrogen. The packing in the crystal is assisted by weak C—H

O interactions between acetato groups and neighboring pyridyl rings.
Supporting information
CCDC reference: 2331143
Key indicators
Structure: I
- Single-crystal X-ray study
- T = 293 K
- Mean
(C-C) = 0.003 Å
- R factor = 0.039
- wR factor = 0.098
- Data-to-parameter ratio = 25.7
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT910_ALERT_3_B Missing # of FCF Reflection(s) Below Theta(Min). 13 Note
1 0 0, 0 1 0, 1 1 0, -1 -1 1, 0 -1 1, -1 0 1,
0 0 1, 1 0 1, 0 1 1, 1 1 1, 0 0 2, 0 1 2,
1 1 2,
Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 3.05 Report
PLAT220_ALERT_2_C NonSolvent Resd 1 C Ueq(max)/Ueq(min) Range 3.1 Ratio
PLAT241_ALERT_2_C High 'MainMol' Ueq as Compared to Neighbors of O2 Check
PLAT241_ALERT_2_C High 'MainMol' Ueq as Compared to Neighbors of O3 Check
PLAT242_ALERT_2_C Low 'MainMol' Ueq as Compared to Neighbors of Zn1 Check
PLAT242_ALERT_2_C Low 'MainMol' Ueq as Compared to Neighbors of C12 Check
PLAT242_ALERT_2_C Low 'MainMol' Ueq as Compared to Neighbors of C14 Check
PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... 03 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 2.215 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 2 Report
0 0 11, 1 1 14,
Alert level G
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K) 293 Check
PLAT200_ALERT_1_G Reported _diffrn_ambient_temperature ..... (K) 293 Check
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) Zn1 --O2 . 24.6 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) Zn1 --O3 . 35.8 s.u.
PLAT303_ALERT_2_G Full Occupancy Atom H1 with # Connections 2.00 Check
PLAT778_ALERT_2_G Check O..H..X Bond in CIF: O5 --H1 1.32 Ang.
PLAT794_ALERT_5_G Tentative Bond Valency for Zn1 (II) . 1.76 Info
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters 1 Info
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 612 Note
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ........... 1.8 Low
PLAT969_ALERT_5_G The 'Henn et al.' R-Factor-gap value ........... 2.52 Note
Predicted wR2: Based on SigI 2 3.89 or SHELX Weight 9.71
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 11 Info
PLAT992_ALERT_5_G Repd & Actual _reflns_number_gt Values Differ by 2 Check
0 ALERT level A = Most likely a serious problem - resolve or explain
1 ALERT level B = A potentially serious problem, consider carefully
10 ALERT level C = Check. Ensure it is not caused by an omission or oversight
13 ALERT level G = General information/check it is not something unexpected
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
12 ALERT type 2 Indicator that the structure model may be wrong or deficient
4 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
3 ALERT type 5 Informative message, check
Bis[µ-bis(pyridin-2-yl)methanone oxime-
κ3N:
N',
N'']bis[diacetato-
κ2O,
O';
κO-zinc(II)]
top
Crystal data top
[Zn2(C2H3O2)4(C11H9N3O)2] | Z = 1 |
Mr = 765.34 | F(000) = 392 |
Triclinic, P1 | Dx = 1.558 Mg m−3 |
a = 8.3549 (7) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.3366 (8) Å | Cell parameters from 4170 reflections |
c = 12.3971 (7) Å | θ = 4.5–33.0° |
α = 69.409 (7)° | µ = 1.54 mm−1 |
β = 75.524 (6)° | T = 293 K |
γ = 65.217 (8)° | Block, colorless |
V = 815.88 (13) Å3 | 0.35 × 0.32 × 0.31 mm |
Data collection top
Xcalibur, Sapphire3 diffractometer | 5737 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 4546 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
Detector resolution: 16.1790 pixels mm-1 | θmax = 33.6°, θmin = 4.2° |
ω scans | h = −11→12 |
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2019) | k = −13→13 |
Tmin = 0.907, Tmax = 1.000 | l = −18→18 |
10420 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: iterative |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.039 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.098 | w = 1/[σ2(Fo2) + (0.0443P)2 + 0.1935P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
5737 reflections | Δρmax = 0.66 e Å−3 |
223 parameters | Δρmin = −0.22 e Å−3 |
0 restraints | |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Hydrogen atoms on sp2 and sp3 carbons were placed at calculated positions with a
C—H distance of 0.93?Å and 0.96?Å and were included in the refinement in
riding motion approximation with Uiso = 1.2Ueq or 1.5Ueq of the carrier atom,
respectively. The position and thermal parameters for the oxime hydrogen were
allowed to refine freely. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Zn1 | 0.34622 (3) | 0.46689 (2) | 0.21836 (2) | 0.03562 (8) | |
O1 | 0.3171 (2) | 0.81600 (16) | 0.04557 (12) | 0.0489 (4) | |
O2 | 0.2284 (2) | 0.3158 (2) | 0.35870 (14) | 0.0625 (4) | |
O3 | 0.0490 (3) | 0.5591 (2) | 0.28225 (15) | 0.0738 (5) | |
O4 | 0.4272 (2) | 0.56182 (17) | 0.31195 (12) | 0.0517 (4) | |
O5 | 0.3442 (3) | 0.83015 (19) | 0.23171 (15) | 0.0721 (6) | |
N1 | 0.3011 (2) | 0.38026 (17) | 0.08947 (13) | 0.0362 (3) | |
N2 | 0.3064 (2) | 0.66897 (16) | 0.06028 (12) | 0.0338 (3) | |
N3 | 0.3964 (2) | 0.73732 (16) | −0.23140 (12) | 0.0327 (3) | |
C1 | 0.2935 (3) | 0.2329 (2) | 0.10808 (19) | 0.0475 (5) | |
H1A | 0.318212 | 0.155161 | 0.179385 | 0.057* | |
C2 | 0.2505 (3) | 0.1924 (2) | 0.0253 (2) | 0.0549 (6) | |
H2 | 0.247728 | 0.088449 | 0.040771 | 0.066* | |
C3 | 0.2119 (3) | 0.3053 (3) | −0.0797 (2) | 0.0523 (5) | |
H3 | 0.180763 | 0.280147 | −0.135924 | 0.063* | |
C4 | 0.2202 (3) | 0.4589 (2) | −0.10074 (17) | 0.0410 (4) | |
H4 | 0.194267 | 0.538517 | −0.171163 | 0.049* | |
C5 | 0.2675 (2) | 0.49042 (19) | −0.01513 (14) | 0.0314 (3) | |
C6 | 0.2823 (2) | 0.64842 (18) | −0.03036 (13) | 0.0300 (3) | |
C7 | 0.2681 (2) | 0.77575 (19) | −0.14482 (14) | 0.0310 (3) | |
C8 | 0.1286 (3) | 0.9258 (2) | −0.15985 (17) | 0.0434 (4) | |
H8 | 0.042857 | 0.949951 | −0.097911 | 0.052* | |
C9 | 0.1179 (3) | 1.0396 (2) | −0.26807 (19) | 0.0523 (5) | |
H9 | 0.025274 | 1.141321 | −0.279936 | 0.063* | |
C10 | 0.2468 (3) | 0.9997 (2) | −0.35777 (18) | 0.0489 (5) | |
H10 | 0.241831 | 1.073160 | −0.431699 | 0.059* | |
C11 | 0.3830 (3) | 0.8493 (2) | −0.33611 (15) | 0.0419 (4) | |
H11 | 0.470518 | 0.823590 | −0.396915 | 0.050* | |
C12 | 0.0764 (3) | 0.4213 (3) | 0.35166 (18) | 0.0533 (5) | |
C13 | −0.0764 (4) | 0.3756 (5) | 0.4298 (3) | 0.0938 (12) | |
H13A | −0.181804 | 0.435492 | 0.391611 | 0.141* | |
H13B | −0.096138 | 0.402581 | 0.501117 | 0.141* | |
H13C | −0.047996 | 0.259790 | 0.446085 | 0.141* | |
C14 | 0.4072 (3) | 0.7035 (2) | 0.30937 (16) | 0.0426 (4) | |
C15 | 0.4641 (4) | 0.7266 (3) | 0.4055 (2) | 0.0684 (7) | |
H15A | 0.461453 | 0.638302 | 0.474543 | 0.103* | |
H15B | 0.384817 | 0.829313 | 0.420185 | 0.103* | |
H15C | 0.582636 | 0.726925 | 0.383512 | 0.103* | |
H1 | 0.325 (5) | 0.821 (4) | 0.132 (3) | 0.116 (13)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Zn1 | 0.04561 (13) | 0.02653 (10) | 0.02801 (10) | −0.00898 (8) | −0.00571 (8) | −0.00425 (7) |
O1 | 0.0854 (11) | 0.0274 (6) | 0.0412 (7) | −0.0243 (7) | −0.0195 (7) | −0.0054 (5) |
O2 | 0.0476 (9) | 0.0701 (11) | 0.0524 (9) | −0.0126 (8) | −0.0018 (7) | −0.0110 (8) |
O3 | 0.0920 (14) | 0.0576 (11) | 0.0510 (10) | −0.0185 (10) | −0.0065 (9) | −0.0037 (8) |
O4 | 0.0768 (11) | 0.0382 (7) | 0.0431 (7) | −0.0183 (7) | −0.0202 (7) | −0.0095 (6) |
O5 | 0.1310 (17) | 0.0374 (8) | 0.0516 (9) | −0.0177 (9) | −0.0432 (10) | −0.0107 (7) |
N1 | 0.0459 (8) | 0.0255 (6) | 0.0353 (7) | −0.0141 (6) | −0.0083 (6) | −0.0028 (5) |
N2 | 0.0482 (8) | 0.0231 (6) | 0.0302 (6) | −0.0126 (6) | −0.0065 (6) | −0.0068 (5) |
N3 | 0.0411 (8) | 0.0261 (6) | 0.0263 (6) | −0.0082 (6) | −0.0082 (5) | −0.0043 (5) |
C1 | 0.0612 (12) | 0.0276 (8) | 0.0519 (11) | −0.0198 (8) | −0.0135 (10) | 0.0001 (7) |
C2 | 0.0700 (15) | 0.0314 (9) | 0.0726 (15) | −0.0253 (10) | −0.0184 (12) | −0.0104 (9) |
C3 | 0.0655 (14) | 0.0443 (11) | 0.0614 (13) | −0.0246 (10) | −0.0176 (11) | −0.0188 (9) |
C4 | 0.0533 (11) | 0.0351 (9) | 0.0398 (9) | −0.0190 (8) | −0.0126 (8) | −0.0083 (7) |
C5 | 0.0364 (8) | 0.0251 (7) | 0.0319 (7) | −0.0107 (6) | −0.0055 (6) | −0.0070 (6) |
C6 | 0.0360 (8) | 0.0231 (7) | 0.0281 (7) | −0.0092 (6) | −0.0046 (6) | −0.0052 (5) |
C7 | 0.0396 (8) | 0.0241 (7) | 0.0292 (7) | −0.0109 (6) | −0.0097 (6) | −0.0046 (5) |
C8 | 0.0458 (10) | 0.0310 (8) | 0.0399 (9) | −0.0036 (7) | −0.0058 (8) | −0.0069 (7) |
C9 | 0.0523 (12) | 0.0321 (9) | 0.0515 (12) | −0.0005 (8) | −0.0151 (9) | 0.0004 (8) |
C10 | 0.0546 (12) | 0.0396 (10) | 0.0379 (9) | −0.0120 (9) | −0.0167 (9) | 0.0073 (7) |
C11 | 0.0472 (10) | 0.0395 (9) | 0.0291 (8) | −0.0110 (8) | −0.0084 (7) | −0.0014 (7) |
C12 | 0.0519 (12) | 0.0612 (13) | 0.0353 (9) | −0.0152 (10) | −0.0035 (8) | −0.0081 (9) |
C13 | 0.0545 (16) | 0.121 (3) | 0.0676 (18) | −0.0295 (18) | 0.0021 (13) | 0.0081 (17) |
C14 | 0.0539 (11) | 0.0412 (9) | 0.0349 (9) | −0.0148 (8) | −0.0078 (8) | −0.0149 (7) |
C15 | 0.107 (2) | 0.0603 (14) | 0.0537 (13) | −0.0356 (15) | −0.0343 (14) | −0.0118 (11) |
Geometric parameters (Å, º) top
Zn1—O2 | 2.1369 (17) | C3—H3 | 0.9300 |
Zn1—O3 | 2.289 (2) | C3—C4 | 1.393 (3) |
Zn1—O4 | 2.0513 (14) | C4—H4 | 0.9300 |
Zn1—N1 | 2.1944 (16) | C4—C5 | 1.377 (3) |
Zn1—N2 | 2.1702 (14) | C5—C6 | 1.474 (2) |
Zn1—N3i | 2.1921 (14) | C6—C7 | 1.490 (2) |
Zn1—C12 | 2.538 (2) | C7—C8 | 1.383 (2) |
O1—N2 | 1.3581 (18) | C8—H8 | 0.9300 |
O1—H1 | 1.11 (4) | C8—C9 | 1.384 (3) |
O2—C12 | 1.240 (3) | C9—H9 | 0.9300 |
O3—C12 | 1.233 (3) | C9—C10 | 1.375 (3) |
O4—C14 | 1.251 (2) | C10—H10 | 0.9300 |
O5—C14 | 1.238 (2) | C10—C11 | 1.374 (3) |
O5—H1 | 1.32 (4) | C11—H11 | 0.9300 |
N1—C1 | 1.339 (2) | C12—C13 | 1.516 (4) |
N1—C5 | 1.349 (2) | C13—H13A | 0.9600 |
N2—C6 | 1.279 (2) | C13—H13B | 0.9600 |
N3—C7 | 1.343 (2) | C13—H13C | 0.9600 |
N3—C11 | 1.346 (2) | C14—C15 | 1.498 (3) |
C1—H1A | 0.9300 | C15—H15A | 0.9600 |
C1—C2 | 1.377 (3) | C15—H15B | 0.9600 |
C2—H2 | 0.9300 | C15—H15C | 0.9600 |
C2—C3 | 1.368 (3) | | |
| | | |
O2—Zn1—O3 | 58.16 (6) | C5—C4—C3 | 118.68 (18) |
O2—Zn1—N1 | 92.26 (6) | C5—C4—H4 | 120.7 |
O2—Zn1—N2 | 146.35 (6) | N1—C5—C4 | 122.62 (15) |
O2—Zn1—N3i | 89.78 (6) | N1—C5—C6 | 114.95 (14) |
O2—Zn1—C12 | 29.18 (7) | C4—C5—C6 | 122.42 (15) |
O3—Zn1—C12 | 29.01 (7) | N2—C6—C5 | 115.96 (14) |
O4—Zn1—O2 | 99.02 (7) | N2—C6—C7 | 122.71 (14) |
O4—Zn1—O3 | 98.14 (7) | C5—C6—C7 | 121.32 (14) |
O4—Zn1—N1 | 168.00 (6) | N3—C7—C6 | 116.84 (14) |
O4—Zn1—N2 | 98.84 (6) | N3—C7—C8 | 122.22 (15) |
O4—Zn1—N3i | 88.29 (6) | C8—C7—C6 | 120.94 (16) |
O4—Zn1—C12 | 100.79 (7) | C7—C8—H8 | 120.4 |
N1—Zn1—O3 | 91.27 (7) | C7—C8—C9 | 119.26 (18) |
N1—Zn1—C12 | 91.05 (7) | C9—C8—H8 | 120.4 |
N2—Zn1—O3 | 91.18 (6) | C8—C9—H9 | 120.6 |
N2—Zn1—N1 | 73.40 (5) | C10—C9—C8 | 118.83 (18) |
N2—Zn1—N3i | 119.03 (6) | C10—C9—H9 | 120.6 |
N2—Zn1—C12 | 118.85 (7) | C9—C10—H10 | 120.6 |
N3i—Zn1—O3 | 147.87 (6) | C11—C10—C9 | 118.74 (17) |
N3i—Zn1—N1 | 87.66 (6) | C11—C10—H10 | 120.6 |
N3i—Zn1—C12 | 118.87 (6) | N3—C11—C10 | 123.36 (18) |
N2—O1—H1 | 107.4 (19) | N3—C11—H11 | 118.3 |
C12—O2—Zn1 | 93.65 (15) | C10—C11—H11 | 118.3 |
C12—O3—Zn1 | 86.75 (16) | O2—C12—Zn1 | 57.18 (12) |
C14—O4—Zn1 | 134.88 (14) | O2—C12—C13 | 118.1 (2) |
C14—O5—H1 | 120.5 (16) | O3—C12—Zn1 | 64.23 (14) |
C1—N1—Zn1 | 125.79 (13) | O3—C12—O2 | 121.3 (2) |
C1—N1—C5 | 117.95 (16) | O3—C12—C13 | 120.6 (2) |
C5—N1—Zn1 | 116.13 (11) | C13—C12—Zn1 | 173.8 (2) |
O1—N2—Zn1 | 125.25 (11) | C12—C13—H13A | 109.5 |
C6—N2—Zn1 | 119.18 (11) | C12—C13—H13B | 109.5 |
C6—N2—O1 | 115.40 (13) | C12—C13—H13C | 109.5 |
C7—N3—Zn1i | 127.73 (11) | H13A—C13—H13B | 109.5 |
C7—N3—C11 | 117.57 (15) | H13A—C13—H13C | 109.5 |
C11—N3—Zn1i | 113.67 (12) | H13B—C13—H13C | 109.5 |
N1—C1—H1A | 118.9 | O4—C14—C15 | 119.21 (19) |
N1—C1—C2 | 122.28 (18) | O5—C14—O4 | 125.11 (18) |
C2—C1—H1A | 118.9 | O5—C14—C15 | 115.68 (19) |
C1—C2—H2 | 120.1 | C14—C15—H15A | 109.5 |
C3—C2—C1 | 119.88 (18) | C14—C15—H15B | 109.5 |
C3—C2—H2 | 120.1 | C14—C15—H15C | 109.5 |
C2—C3—H3 | 120.7 | H15A—C15—H15B | 109.5 |
C2—C3—C4 | 118.55 (19) | H15A—C15—H15C | 109.5 |
C4—C3—H3 | 120.7 | H15B—C15—H15C | 109.5 |
C3—C4—H4 | 120.7 | | |
| | | |
Zn1—O2—C12—O3 | −3.7 (3) | N2—C6—C7—C8 | −64.7 (3) |
Zn1—O2—C12—C13 | 175.4 (2) | N3—C7—C8—C9 | 1.3 (3) |
Zn1—O3—C12—O2 | 3.4 (3) | C1—N1—C5—C4 | 2.3 (3) |
Zn1—O3—C12—C13 | −175.6 (3) | C1—N1—C5—C6 | −178.61 (17) |
Zn1—O4—C14—O5 | −10.1 (4) | C1—C2—C3—C4 | 1.0 (4) |
Zn1—O4—C14—C15 | 170.56 (18) | C2—C3—C4—C5 | 0.2 (3) |
Zn1—N1—C1—C2 | 174.66 (17) | C3—C4—C5—N1 | −2.0 (3) |
Zn1—N1—C5—C4 | −173.72 (14) | C3—C4—C5—C6 | 179.04 (19) |
Zn1—N1—C5—C6 | 5.3 (2) | C4—C5—C6—N2 | 171.92 (17) |
Zn1—N2—C6—C5 | 5.5 (2) | C4—C5—C6—C7 | −7.5 (3) |
Zn1—N2—C6—C7 | −175.07 (12) | C5—N1—C1—C2 | −1.0 (3) |
Zn1i—N3—C7—C6 | −14.1 (2) | C5—C6—C7—N3 | −65.3 (2) |
Zn1i—N3—C7—C8 | 165.91 (14) | C5—C6—C7—C8 | 114.7 (2) |
Zn1i—N3—C11—C10 | −168.65 (17) | C6—C7—C8—C9 | −178.66 (19) |
O1—N2—C6—C5 | −179.02 (15) | C7—N3—C11—C10 | 0.6 (3) |
O1—N2—C6—C7 | 0.4 (3) | C7—C8—C9—C10 | 0.1 (3) |
N1—C1—C2—C3 | −0.7 (4) | C8—C9—C10—C11 | −1.1 (4) |
N1—C5—C6—N2 | −7.1 (2) | C9—C10—C11—N3 | 0.7 (3) |
N1—C5—C6—C7 | 173.44 (16) | C11—N3—C7—C6 | 178.31 (16) |
N2—C6—C7—N3 | 115.34 (19) | C11—N3—C7—C8 | −1.6 (3) |
Symmetry code: (i) −x+1, −y+1, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O5 | 1.11 (4) | 1.32 (4) | 2.428 (2) | 176 (3) |
C2—H2···O1ii | 0.93 | 2.34 | 3.245 (2) | 164 |
C3—H3···O3iii | 0.93 | 2.58 | 3.293 (3) | 134 |
C9—H9···03iv | 0.93 | 2.59 | 3.361 (3) | 141 |
C11—H11···O2i | 0.93 | 2.38 | 2.941 (3) | 119 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x, y−1, z; (iii) −x, −y+1, −z; (iv) −x, −y+2, −z. |