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The structure of the title complex, [Zn2(C2H3O2)4(C11H9N3O)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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314624001226/zl4065sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2414314624001226/zl4065Isup2.hkl
Contains datablock I

CCDC reference: 2331143

Key indicators

Structure: I
  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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

Computing details top

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 = 765.34F(000) = 392
Triclinic, P1Dx = 1.558 Mg m3
a = 8.3549 (7) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.3366 (8) ÅCell parameters from 4170 reflections
c = 12.3971 (7) Åθ = 4.5–33.0°
α = 69.409 (7)°µ = 1.54 mm1
β = 75.524 (6)°T = 293 K
γ = 65.217 (8)°Block, colorless
V = 815.88 (13) Å30.35 × 0.32 × 0.31 mm
Data collection top
Xcalibur, Sapphire3
diffractometer
5737 independent reflections
Radiation source: Enhance (Mo) X-ray Source4546 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
Detector resolution: 16.1790 pixels mm-1θmax = 33.6°, θmin = 4.2°
ω scansh = 1112
Absorption correction: multi-scan
(CrysAlisPro; Rigaku OD, 2019)
k = 1313
Tmin = 0.907, Tmax = 1.000l = 1818
10420 measured reflections
Refinement top
Refinement on F2Primary atom site location: iterative
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.039H 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 reflectionsΔρmax = 0.66 e Å3
223 parametersΔρmin = 0.22 e Å3
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
xyzUiso*/Ueq
Zn10.34622 (3)0.46689 (2)0.21836 (2)0.03562 (8)
O10.3171 (2)0.81600 (16)0.04557 (12)0.0489 (4)
O20.2284 (2)0.3158 (2)0.35870 (14)0.0625 (4)
O30.0490 (3)0.5591 (2)0.28225 (15)0.0738 (5)
O40.4272 (2)0.56182 (17)0.31195 (12)0.0517 (4)
O50.3442 (3)0.83015 (19)0.23171 (15)0.0721 (6)
N10.3011 (2)0.38026 (17)0.08947 (13)0.0362 (3)
N20.3064 (2)0.66897 (16)0.06028 (12)0.0338 (3)
N30.3964 (2)0.73732 (16)0.23140 (12)0.0327 (3)
C10.2935 (3)0.2329 (2)0.10808 (19)0.0475 (5)
H1A0.3182120.1551610.1793850.057*
C20.2505 (3)0.1924 (2)0.0253 (2)0.0549 (6)
H20.2477280.0884490.0407710.066*
C30.2119 (3)0.3053 (3)0.0797 (2)0.0523 (5)
H30.1807630.2801470.1359240.063*
C40.2202 (3)0.4589 (2)0.10074 (17)0.0410 (4)
H40.1942670.5385170.1711630.049*
C50.2675 (2)0.49042 (19)0.01513 (14)0.0314 (3)
C60.2823 (2)0.64842 (18)0.03036 (13)0.0300 (3)
C70.2681 (2)0.77575 (19)0.14482 (14)0.0310 (3)
C80.1286 (3)0.9258 (2)0.15985 (17)0.0434 (4)
H80.0428570.9499510.0979110.052*
C90.1179 (3)1.0396 (2)0.26807 (19)0.0523 (5)
H90.0252741.1413210.2799360.063*
C100.2468 (3)0.9997 (2)0.35777 (18)0.0489 (5)
H100.2418311.0731600.4316990.059*
C110.3830 (3)0.8493 (2)0.33611 (15)0.0419 (4)
H110.4705180.8235900.3969150.050*
C120.0764 (3)0.4213 (3)0.35166 (18)0.0533 (5)
C130.0764 (4)0.3756 (5)0.4298 (3)0.0938 (12)
H13A0.1818040.4354920.3916110.141*
H13B0.0961380.4025810.5011170.141*
H13C0.0479960.2597900.4460850.141*
C140.4072 (3)0.7035 (2)0.30937 (16)0.0426 (4)
C150.4641 (4)0.7266 (3)0.4055 (2)0.0684 (7)
H15A0.4614530.6383020.4745430.103*
H15B0.3848170.8293130.4201850.103*
H15C0.5826360.7269250.3835120.103*
H10.325 (5)0.821 (4)0.132 (3)0.116 (13)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.04561 (13)0.02653 (10)0.02801 (10)0.00898 (8)0.00571 (8)0.00425 (7)
O10.0854 (11)0.0274 (6)0.0412 (7)0.0243 (7)0.0195 (7)0.0054 (5)
O20.0476 (9)0.0701 (11)0.0524 (9)0.0126 (8)0.0018 (7)0.0110 (8)
O30.0920 (14)0.0576 (11)0.0510 (10)0.0185 (10)0.0065 (9)0.0037 (8)
O40.0768 (11)0.0382 (7)0.0431 (7)0.0183 (7)0.0202 (7)0.0095 (6)
O50.1310 (17)0.0374 (8)0.0516 (9)0.0177 (9)0.0432 (10)0.0107 (7)
N10.0459 (8)0.0255 (6)0.0353 (7)0.0141 (6)0.0083 (6)0.0028 (5)
N20.0482 (8)0.0231 (6)0.0302 (6)0.0126 (6)0.0065 (6)0.0068 (5)
N30.0411 (8)0.0261 (6)0.0263 (6)0.0082 (6)0.0082 (5)0.0043 (5)
C10.0612 (12)0.0276 (8)0.0519 (11)0.0198 (8)0.0135 (10)0.0001 (7)
C20.0700 (15)0.0314 (9)0.0726 (15)0.0253 (10)0.0184 (12)0.0104 (9)
C30.0655 (14)0.0443 (11)0.0614 (13)0.0246 (10)0.0176 (11)0.0188 (9)
C40.0533 (11)0.0351 (9)0.0398 (9)0.0190 (8)0.0126 (8)0.0083 (7)
C50.0364 (8)0.0251 (7)0.0319 (7)0.0107 (6)0.0055 (6)0.0070 (6)
C60.0360 (8)0.0231 (7)0.0281 (7)0.0092 (6)0.0046 (6)0.0052 (5)
C70.0396 (8)0.0241 (7)0.0292 (7)0.0109 (6)0.0097 (6)0.0046 (5)
C80.0458 (10)0.0310 (8)0.0399 (9)0.0036 (7)0.0058 (8)0.0069 (7)
C90.0523 (12)0.0321 (9)0.0515 (12)0.0005 (8)0.0151 (9)0.0004 (8)
C100.0546 (12)0.0396 (10)0.0379 (9)0.0120 (9)0.0167 (9)0.0073 (7)
C110.0472 (10)0.0395 (9)0.0291 (8)0.0110 (8)0.0084 (7)0.0014 (7)
C120.0519 (12)0.0612 (13)0.0353 (9)0.0152 (10)0.0035 (8)0.0081 (9)
C130.0545 (16)0.121 (3)0.0676 (18)0.0295 (18)0.0021 (13)0.0081 (17)
C140.0539 (11)0.0412 (9)0.0349 (9)0.0148 (8)0.0078 (8)0.0149 (7)
C150.107 (2)0.0603 (14)0.0537 (13)0.0356 (15)0.0343 (14)0.0118 (11)
Geometric parameters (Å, º) top
Zn1—O22.1369 (17)C3—H30.9300
Zn1—O32.289 (2)C3—C41.393 (3)
Zn1—O42.0513 (14)C4—H40.9300
Zn1—N12.1944 (16)C4—C51.377 (3)
Zn1—N22.1702 (14)C5—C61.474 (2)
Zn1—N3i2.1921 (14)C6—C71.490 (2)
Zn1—C122.538 (2)C7—C81.383 (2)
O1—N21.3581 (18)C8—H80.9300
O1—H11.11 (4)C8—C91.384 (3)
O2—C121.240 (3)C9—H90.9300
O3—C121.233 (3)C9—C101.375 (3)
O4—C141.251 (2)C10—H100.9300
O5—C141.238 (2)C10—C111.374 (3)
O5—H11.32 (4)C11—H110.9300
N1—C11.339 (2)C12—C131.516 (4)
N1—C51.349 (2)C13—H13A0.9600
N2—C61.279 (2)C13—H13B0.9600
N3—C71.343 (2)C13—H13C0.9600
N3—C111.346 (2)C14—C151.498 (3)
C1—H1A0.9300C15—H15A0.9600
C1—C21.377 (3)C15—H15B0.9600
C2—H20.9300C15—H15C0.9600
C2—C31.368 (3)
O2—Zn1—O358.16 (6)C5—C4—C3118.68 (18)
O2—Zn1—N192.26 (6)C5—C4—H4120.7
O2—Zn1—N2146.35 (6)N1—C5—C4122.62 (15)
O2—Zn1—N3i89.78 (6)N1—C5—C6114.95 (14)
O2—Zn1—C1229.18 (7)C4—C5—C6122.42 (15)
O3—Zn1—C1229.01 (7)N2—C6—C5115.96 (14)
O4—Zn1—O299.02 (7)N2—C6—C7122.71 (14)
O4—Zn1—O398.14 (7)C5—C6—C7121.32 (14)
O4—Zn1—N1168.00 (6)N3—C7—C6116.84 (14)
O4—Zn1—N298.84 (6)N3—C7—C8122.22 (15)
O4—Zn1—N3i88.29 (6)C8—C7—C6120.94 (16)
O4—Zn1—C12100.79 (7)C7—C8—H8120.4
N1—Zn1—O391.27 (7)C7—C8—C9119.26 (18)
N1—Zn1—C1291.05 (7)C9—C8—H8120.4
N2—Zn1—O391.18 (6)C8—C9—H9120.6
N2—Zn1—N173.40 (5)C10—C9—C8118.83 (18)
N2—Zn1—N3i119.03 (6)C10—C9—H9120.6
N2—Zn1—C12118.85 (7)C9—C10—H10120.6
N3i—Zn1—O3147.87 (6)C11—C10—C9118.74 (17)
N3i—Zn1—N187.66 (6)C11—C10—H10120.6
N3i—Zn1—C12118.87 (6)N3—C11—C10123.36 (18)
N2—O1—H1107.4 (19)N3—C11—H11118.3
C12—O2—Zn193.65 (15)C10—C11—H11118.3
C12—O3—Zn186.75 (16)O2—C12—Zn157.18 (12)
C14—O4—Zn1134.88 (14)O2—C12—C13118.1 (2)
C14—O5—H1120.5 (16)O3—C12—Zn164.23 (14)
C1—N1—Zn1125.79 (13)O3—C12—O2121.3 (2)
C1—N1—C5117.95 (16)O3—C12—C13120.6 (2)
C5—N1—Zn1116.13 (11)C13—C12—Zn1173.8 (2)
O1—N2—Zn1125.25 (11)C12—C13—H13A109.5
C6—N2—Zn1119.18 (11)C12—C13—H13B109.5
C6—N2—O1115.40 (13)C12—C13—H13C109.5
C7—N3—Zn1i127.73 (11)H13A—C13—H13B109.5
C7—N3—C11117.57 (15)H13A—C13—H13C109.5
C11—N3—Zn1i113.67 (12)H13B—C13—H13C109.5
N1—C1—H1A118.9O4—C14—C15119.21 (19)
N1—C1—C2122.28 (18)O5—C14—O4125.11 (18)
C2—C1—H1A118.9O5—C14—C15115.68 (19)
C1—C2—H2120.1C14—C15—H15A109.5
C3—C2—C1119.88 (18)C14—C15—H15B109.5
C3—C2—H2120.1C14—C15—H15C109.5
C2—C3—H3120.7H15A—C15—H15B109.5
C2—C3—C4118.55 (19)H15A—C15—H15C109.5
C4—C3—H3120.7H15B—C15—H15C109.5
C3—C4—H4120.7
Zn1—O2—C12—O33.7 (3)N2—C6—C7—C864.7 (3)
Zn1—O2—C12—C13175.4 (2)N3—C7—C8—C91.3 (3)
Zn1—O3—C12—O23.4 (3)C1—N1—C5—C42.3 (3)
Zn1—O3—C12—C13175.6 (3)C1—N1—C5—C6178.61 (17)
Zn1—O4—C14—O510.1 (4)C1—C2—C3—C41.0 (4)
Zn1—O4—C14—C15170.56 (18)C2—C3—C4—C50.2 (3)
Zn1—N1—C1—C2174.66 (17)C3—C4—C5—N12.0 (3)
Zn1—N1—C5—C4173.72 (14)C3—C4—C5—C6179.04 (19)
Zn1—N1—C5—C65.3 (2)C4—C5—C6—N2171.92 (17)
Zn1—N2—C6—C55.5 (2)C4—C5—C6—C77.5 (3)
Zn1—N2—C6—C7175.07 (12)C5—N1—C1—C21.0 (3)
Zn1i—N3—C7—C614.1 (2)C5—C6—C7—N365.3 (2)
Zn1i—N3—C7—C8165.91 (14)C5—C6—C7—C8114.7 (2)
Zn1i—N3—C11—C10168.65 (17)C6—C7—C8—C9178.66 (19)
O1—N2—C6—C5179.02 (15)C7—N3—C11—C100.6 (3)
O1—N2—C6—C70.4 (3)C7—C8—C9—C100.1 (3)
N1—C1—C2—C30.7 (4)C8—C9—C10—C111.1 (4)
N1—C5—C6—N27.1 (2)C9—C10—C11—N30.7 (3)
N1—C5—C6—C7173.44 (16)C11—N3—C7—C6178.31 (16)
N2—C6—C7—N3115.34 (19)C11—N3—C7—C81.6 (3)
Symmetry code: (i) x+1, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O51.11 (4)1.32 (4)2.428 (2)176 (3)
C2—H2···O1ii0.932.343.245 (2)164
C3—H3···O3iii0.932.583.293 (3)134
C9—H9···03iv0.932.593.361 (3)141
C11—H11···O2i0.932.382.941 (3)119
Symmetry codes: (i) x+1, y+1, z; (ii) x, y1, z; (iii) x, y+1, z; (iv) x, y+2, z.
 

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