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metal-organic compounds
In the title compound, [Zn(C2H3O2)(C11H12N3O2)(C3H4N2)], the Zn atom is five-coordinate in a ZnN3O2 trigonal-bipyramidal enviroment. Adjacent molecules are linked by an intermolecular hydrogen bond into a chain running along the a axis of the monoclinic cell.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804009912/ng6025sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804009912/ng6025Isup2.hkl |
CCDC reference: 239116
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.036
- wR factor = 0.089
- Data-to-parameter ratio = 16.9
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT430_ALERT_2_B Short Inter D...A Contact O4 .. O4 .. 2.80 Ang.
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
Crystal data top
[Zn(C2H3O2)(C11H12N3O2)(C3H4N2)] | F(000) = 848 |
Mr = 410.75 | Dx = 1.512 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 11353 reflections |
a = 7.731 (2) Å | θ = 3.4–27.4° |
b = 18.334 (4) Å | µ = 1.39 mm−1 |
c = 12.931 (3) Å | T = 293 K |
β = 100.07 (3)° | Prism, yellow |
V = 1804.6 (8) Å3 | 0.37 × 0.25 × 0.18 mm |
Z = 4 |
Data collection top
Rigaku RAXIS-RAPID diffractometer | 4122 independent reflections |
Radiation source: fine-focus sealed tube | 3431 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
Detector resolution: 10 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
ω scans | h = −10→10 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −23→23 |
Tmin = 0.626, Tmax = 0.788 | l = −16→16 |
16947 measured reflections |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.089 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0509P)2 + 0.4702P] where P = (Fo2 + 2Fc2)/3 |
4122 reflections | (Δ/σ)max < 0.001 |
244 parameters | Δρmax = 0.47 e Å−3 |
2 restraints | Δρmin = −0.26 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Zn1 | 0.24758 (3) | 0.59385 (1) | 0.26486 (2) | 0.03707 (9) | |
N1 | 0.3754 (2) | 0.6577 (1) | 0.4087 (1) | 0.0447 (4) | |
N2 | 0.2141 (2) | 0.7018 (1) | 0.2298 (1) | 0.0388 (4) | |
N3 | 0.1204 (2) | 0.7198 (1) | 0.1328 (1) | 0.0415 (4) | |
N4 | 0.4694 (2) | 0.55362 (9) | 0.2279 (1) | 0.0368 (4) | |
N5 | 0.7476 (2) | 0.5302 (1) | 0.2388 (2) | 0.0475 (4) | |
O1 | 0.0921 (2) | 0.59408 (7) | 0.1144 (1) | 0.0453 (4) | |
O2 | 0.4626 (3) | 0.63416 (9) | 0.5054 (1) | 0.0583 (5) | |
O3 | 0.0988 (2) | 0.52482 (8) | 0.3268 (1) | 0.0399 (3) | |
O4 | 0.3254 (2) | 0.49637 (9) | 0.4484 (1) | 0.0599 (5) | |
C1 | 0.4612 (3) | 0.7792 (1) | 0.4782 (2) | 0.0533 (6) | |
C2 | 0.3769 (3) | 0.7269 (1) | 0.3964 (2) | 0.0397 (4) | |
C3 | 0.2841 (3) | 0.7526 (1) | 0.2925 (2) | 0.0398 (4) | |
C4 | 0.2706 (3) | 0.8320 (1) | 0.2651 (2) | 0.0578 (6) | |
C5 | 0.0650 (2) | 0.6592 (1) | 0.0810 (2) | 0.0368 (4) | |
C6 | −0.0403 (3) | 0.6709 (1) | −0.0263 (2) | 0.0378 (4) | |
C7 | −0.0628 (3) | 0.7407 (1) | −0.0695 (2) | 0.0477 (5) | |
C8 | −0.1626 (3) | 0.7510 (1) | −0.1677 (2) | 0.0565 (6) | |
C9 | −0.2430 (3) | 0.6926 (2) | −0.2240 (2) | 0.0568 (6) | |
C10 | −0.2196 (3) | 0.6231 (2) | −0.1824 (2) | 0.0515 (6) | |
C11 | −0.1175 (3) | 0.6120 (1) | −0.0849 (2) | 0.0421 (5) | |
C12 | 0.6186 (3) | 0.5413 (1) | 0.2920 (2) | 0.0438 (5) | |
C13 | 0.6815 (3) | 0.5350 (2) | 0.1359 (2) | 0.0638 (7) | |
C14 | 0.5081 (3) | 0.5492 (2) | 0.1291 (2) | 0.0536 (6) | |
C15 | 0.0732 (3) | 0.4221 (1) | 0.4356 (2) | 0.0509 (5) | |
C16 | 0.1751 (3) | 0.4851 (1) | 0.4034 (2) | 0.0385 (4) | |
H1A | 0.4377 | 0.7643 | 0.5456 | 0.080* | |
H1B | 0.4144 | 0.8272 | 0.4621 | 0.080* | |
H1C | 0.5858 | 0.7798 | 0.4797 | 0.080* | |
H4A | 0.2689 | 0.8378 | 0.1911 | 0.087* | |
H4B | 0.3699 | 0.8574 | 0.3036 | 0.087* | |
H4C | 0.1644 | 0.8515 | 0.2828 | 0.087* | |
H7 | −0.0101 | 0.7805 | −0.0319 | 0.057* | |
H8 | −0.1760 | 0.7977 | −0.1962 | 0.068* | |
H9 | −0.3124 | 0.6999 | −0.2895 | 0.068* | |
H10 | −0.2729 | 0.5836 | −0.2203 | 0.062* | |
H11 | −0.1003 | 0.5650 | −0.0582 | 0.051* | |
H12 | 0.6315 | 0.5405 | 0.3648 | 0.053* | |
H13 | 0.7425 | 0.5297 | 0.0804 | 0.077* | |
H14 | 0.4281 | 0.5551 | 0.0670 | 0.064* | |
H15A | 0.1005 | 0.3788 | 0.3999 | 0.076* | |
H15B | −0.0502 | 0.4321 | 0.4175 | 0.076* | |
H15C | 0.1042 | 0.4150 | 0.5101 | 0.076* | |
H17 | 0.435 (5) | 0.5896 (7) | 0.504 (3) | 0.087* | |
H18 | 0.855 (2) | 0.527 (1) | 0.268 (2) | 0.077* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.0287 (1) | 0.0398 (1) | 0.0421 (1) | 0.00181 (9) | 0.00455 (9) | 0.0030 (1) |
N1 | 0.046 (1) | 0.046 (1) | 0.0398 (9) | 0.0022 (8) | −0.0006 (7) | 0.0003 (8) |
N2 | 0.0334 (8) | 0.0419 (9) | 0.0401 (9) | 0.0047 (7) | 0.0034 (7) | −0.0003 (7) |
N3 | 0.0400 (9) | 0.0435 (9) | 0.0388 (9) | 0.0055 (8) | 0.0008 (7) | 0.0016 (7) |
N4 | 0.0279 (8) | 0.0430 (9) | 0.0387 (9) | 0.0014 (7) | 0.0036 (6) | 0.0040 (7) |
N5 | 0.0269 (8) | 0.057 (1) | 0.057 (1) | 0.0012 (8) | 0.0035 (8) | 0.0033 (9) |
O1 | 0.0437 (8) | 0.0412 (8) | 0.0459 (8) | −0.0010 (6) | −0.0063 (6) | 0.0037 (6) |
O2 | 0.073 (1) | 0.0521 (9) | 0.0432 (9) | 0.0061 (9) | −0.0075 (8) | 0.0024 (8) |
O3 | 0.0278 (6) | 0.0507 (8) | 0.0398 (7) | −0.0003 (6) | 0.0019 (5) | 0.0081 (6) |
O4 | 0.0393 (8) | 0.060 (1) | 0.072 (1) | −0.0087 (7) | −0.0161 (7) | 0.0227 (9) |
C1 | 0.057 (1) | 0.053 (1) | 0.047 (1) | −0.003 (1) | 0.000 (1) | −0.010 (1) |
C2 | 0.0307 (9) | 0.045 (1) | 0.043 (1) | 0.0008 (8) | 0.0059 (8) | −0.0057 (9) |
C3 | 0.032 (1) | 0.041 (1) | 0.045 (1) | 0.0033 (8) | 0.0053 (8) | −0.0025 (9) |
C4 | 0.060 (2) | 0.043 (1) | 0.065 (2) | 0.002 (1) | −0.005 (1) | 0.000 (1) |
C5 | 0.0290 (9) | 0.044 (1) | 0.038 (1) | 0.0025 (8) | 0.0069 (8) | 0.0023 (8) |
C6 | 0.0315 (9) | 0.047 (1) | 0.036 (1) | 0.0050 (8) | 0.0090 (8) | 0.0022 (8) |
C7 | 0.052 (1) | 0.046 (1) | 0.045 (1) | 0.005 (1) | 0.007 (1) | 0.001 (1) |
C8 | 0.063 (2) | 0.058 (1) | 0.048 (1) | 0.012 (1) | 0.009 (1) | 0.012 (1) |
C9 | 0.057 (2) | 0.076 (2) | 0.035 (1) | 0.011 (1) | 0.002 (1) | 0.005 (1) |
C10 | 0.052 (1) | 0.064 (2) | 0.038 (1) | −0.004 (1) | 0.006 (1) | −0.009 (1) |
C11 | 0.042 (1) | 0.047 (1) | 0.038 (1) | 0.0015 (9) | 0.0091 (8) | 0.0001 (9) |
C12 | 0.033 (1) | 0.056 (1) | 0.040 (1) | 0.0032 (9) | 0.0007 (8) | 0.000 (1) |
C13 | 0.045 (1) | 0.099 (2) | 0.052 (1) | 0.010 (1) | 0.021 (1) | 0.016 (1) |
C14 | 0.040 (1) | 0.082 (2) | 0.039 (1) | 0.008 (1) | 0.0062 (9) | 0.014 (1) |
C15 | 0.057 (1) | 0.051 (1) | 0.044 (1) | −0.015 (1) | 0.007 (1) | 0.002 (1) |
C16 | 0.036 (1) | 0.043 (1) | 0.035 (1) | −0.0010 (8) | 0.0045 (8) | 0.0010 (8) |
Geometric parameters (Å, º) top
Zn1—N1 | 2.272 (2) | C3—C4 | 1.497 (3) |
Zn1—N2 | 2.037 (2) | C4—H4A | 0.9600 |
Zn1—N4 | 2.000 (2) | C4—H4B | 0.9600 |
Zn1—O1 | 2.100 (2) | C4—H4C | 0.9600 |
Zn1—O3 | 1.972 (1) | C5—C6 | 1.496 (3) |
N1—C2 | 1.279 (3) | C6—C7 | 1.395 (3) |
N2—N3 | 1.374 (2) | C6—C11 | 1.392 (3) |
N2—C3 | 1.290 (3) | C7—C8 | 1.379 (3) |
N3—C5 | 1.329 (3) | C7—H7 | 0.9300 |
O1—C5 | 1.274 (2) | C8—C9 | 1.380 (4) |
O2—N1 | 1.382 (2) | C8—H8 | 0.9300 |
C2—C3 | 1.485 (3) | C9—C10 | 1.382 (4) |
N4—C12 | 1.316 (2) | C9—H9 | 0.9300 |
N4—C14 | 1.365 (3) | C10—C11 | 1.380 (3) |
N5—C12 | 1.323 (3) | C10—H10 | 0.9300 |
N5—C13 | 1.343 (3) | C11—H11 | 0.9300 |
N5—H18 | 0.85 (3) | C12—H12 | 0.9300 |
O2—H17 | 0.84 (3) | C13—C14 | 1.353 (3) |
O3—C16 | 1.286 (2) | C13—H13 | 0.9300 |
O4—C16 | 1.223 (2) | C14—H14 | 0.9300 |
C1—C2 | 1.491 (3) | C15—C16 | 1.497 (3) |
C1—H1A | 0.9600 | C15—H15A | 0.9600 |
C1—H1B | 0.9600 | C15—H15B | 0.9600 |
C1—H1C | 0.9600 | C15—H15C | 0.9600 |
N2—Zn1—N1 | 72.65 (7) | C5—O1—Zn1 | 110.5 (1) |
N2—Zn1—O1 | 76.23 (6) | C6—C7—H7 | 119.8 |
N4—Zn1—N1 | 96.71 (7) | C6—C11—H11 | 119.8 |
N4—Zn1—N2 | 112.70 (7) | C7—C6—C5 | 120.8 (2) |
N4—Zn1—O1 | 98.95 (7) | C7—C8—C9 | 120.5 (2) |
O1—Zn1—N1 | 148.61 (6) | C7—C8—H8 | 119.8 |
O3—Zn1—N1 | 101.48 (7) | C8—C7—C6 | 120.4 (2) |
O3—Zn1—N2 | 130.82 (6) | C8—C7—H7 | 119.8 |
O3—Zn1—N4 | 116.48 (6) | C8—C9—C10 | 119.6 (2) |
O3—Zn1—O1 | 95.60 (6) | C8—C9—H9 | 120.2 |
N1—O2—H17 | 102 (3) | C9—C8—H8 | 119.8 |
N1—C2—C1 | 124.2 (2) | C9—C10—H10 | 119.8 |
N1—C2—C3 | 114.5 (2) | C10—C9—H9 | 120.2 |
N3—N2—Zn1 | 117.5 (1) | C10—C11—C6 | 120.3 (2) |
N2—C3—C2 | 115.0 (2) | C10—C11—H11 | 119.8 |
N2—C3—C4 | 123.3 (2) | C11—C6—C7 | 118.8 (2) |
N3—C5—C6 | 115.0 (2) | C11—C6—C5 | 120.4 (2) |
N4—C12—N5 | 110.9 (2) | C11—C10—C9 | 120.4 (2) |
N4—C12—H12 | 124.5 | C11—C10—H10 | 119.8 |
N4—C14—H14 | 125.5 | C12—N4—C14 | 105.6 (2) |
N5—C12—H12 | 124.5 | C12—N4—Zn1 | 127.4 (2) |
N5—C13—C14 | 106.2 (2) | C12—N5—C13 | 108.3 (2) |
N5—C13—H13 | 126.9 | C12—N5—H18 | 124 (2) |
O1—C5—N3 | 126.3 (2) | C13—N5—H18 | 128 (2) |
O1—C5—C6 | 118.7 (2) | C13—C14—N4 | 109.1 (2) |
O2—N1—Zn1 | 130.8 (1) | C13—C14—H14 | 125.5 |
O3—C16—C15 | 117.3 (2) | C14—N4—Zn1 | 125.6 (1) |
O4—C16—O3 | 122.7 (2) | C14—C13—H13 | 126.9 |
O4—C16—C15 | 120.0 (2) | C16—O3—Zn1 | 117.1 (1) |
C2—N1—Zn1 | 114.9 (1) | C16—C15—H15A | 109.5 |
C2—N1—O2 | 114.1 (2) | C16—C15—H15B | 109.5 |
C2—C1—H1C | 109.5 | C16—C15—H15C | 109.5 |
C2—C1—H1A | 109.5 | H1A—C1—H1B | 109.5 |
C2—C1—H1B | 109.5 | H1A—C1—H1C | 109.5 |
C2—C3—C4 | 121.7 (2) | H1B—C1—H1C | 109.5 |
C3—N2—Zn1 | 122.6 (2) | H4A—C4—H4B | 109.5 |
C3—N2—N3 | 119.8 (2) | H4A—C4—H4C | 109.5 |
C3—C2—C1 | 121.3 (2) | H4B—C4—H4C | 109.5 |
C3—C4—H4A | 109.5 | H15A—C15—H15B | 109.5 |
C3—C4—H4B | 109.5 | H15A—C15—H15C | 109.5 |
C3—C4—H4C | 109.5 | H15B—C15—H15C | 109.5 |
C5—N3—N2 | 109.4 (2) | ||
Zn1—N1—C2—C1 | −177.0 (2) | N4—Zn1—O3—C16 | 48.8 (2) |
Zn1—N1—C2—C3 | 3.9 (2) | N5—C13—C14—N4 | 0.5 (3) |
Zn1—N2—N3—C5 | 1.6 (2) | O1—Zn1—N1—O2 | 172.1 (2) |
Zn1—N2—C3—C2 | −5.5 (3) | O1—Zn1—N1—C2 | −12.8 (2) |
Zn1—N2—C3—C4 | 175.9 (2) | O1—Zn1—N2—N3 | −2.0 (1) |
Zn1—N4—C12—N5 | −166.1 (2) | O1—Zn1—N2—C3 | −178.6 (2) |
Zn1—N4—C14—C13 | 166.2 (2) | O1—Zn1—N4—C12 | 179.4 (2) |
Zn1—O1—C5—N3 | −1.9 (3) | O1—Zn1—N4—C14 | 15.3 (2) |
Zn1—O1—C5—C6 | 178.7 (1) | O1—Zn1—O3—C16 | 151.8 (2) |
Zn1—O3—C16—O4 | 11.6 (3) | O1—C5—C6—C7 | −175.3 (2) |
Zn1—O3—C16—C15 | −167.2 (2) | O1—C5—C6—C11 | 4.6 (3) |
N1—Zn1—N2—N3 | −177.8 (2) | O2—N1—C2—C1 | −1.1 (3) |
N1—Zn1—N2—C3 | 5.6 (2) | O2—N1—C2—C3 | 179.8 (2) |
N1—Zn1—N4—C12 | 26.7 (2) | O3—Zn1—N1—O2 | 50.5 (2) |
N1—Zn1—N4—C14 | −137.4 (2) | O3—Zn1—N1—C2 | −134.4 (2) |
N1—Zn1—O1—C5 | 9.7 (2) | O3—Zn1—N2—N3 | −87.5 (2) |
N1—Zn1—O3—C16 | −54.7 (2) | O3—Zn1—N2—C3 | 96.0 (2) |
N1—C2—C3—N2 | 0.5 (3) | O3—Zn1—N4—C12 | −79.7 (2) |
N1—C2—C3—C4 | 179.1 (2) | O3—Zn1—N4—C14 | 116.2 (2) |
N2—Zn1—N1—O2 | 180.0 (2) | O3—Zn1—O1—C5 | 132.7 (1) |
N2—Zn1—N1—C2 | −5.0 (2) | C1—C2—C3—N2 | −178.7 (2) |
N2—Zn1—N4—C12 | 100.7 (2) | C1—C2—C3—C4 | −0.1 (3) |
N2—Zn1—N4—C14 | −63.4 (2) | C3—N2—N3—C5 | 178.3 (2) |
N2—Zn1—O1—C5 | 2.0 (2) | C5—C6—C7—C8 | −178.9 (2) |
N2—Zn1—O3—C16 | −131.6 (1) | C5—C6—C11—C10 | 177.8 (2) |
N2—N3—C5—O1 | 0.3 (3) | C6—C7—C8—C9 | 0.6 (4) |
N2—N3—C5—C6 | 179.7 (2) | C7—C6—C11—C10 | −2.3 (3) |
N3—N2—C3—C2 | 178.0 (2) | C7—C8—C9—C10 | −1.5 (4) |
N3—N2—C3—C4 | −0.6 (3) | C8—C9—C10—C11 | 0.4 (4) |
N3—C5—C6—C7 | 5.3 (3) | C9—C10—C11—C6 | 1.5 (4) |
N3—C5—C6—C11 | −174.8 (2) | C11—C6—C7—C8 | 1.2 (3) |
N4—Zn1—N1—O2 | −68.3 (2) | C12—N4—C14—C13 | −0.7 (3) |
N4—Zn1—N1—C2 | 106.8 (2) | C12—N5—C13—C14 | −0.2 (3) |
N4—Zn1—N2—N3 | 92.1 (2) | C13—N5—C12—N4 | −0.2 (3) |
N4—Zn1—N2—C3 | −84.5 (2) | C14—N4—C12—N5 | 0.5 (3) |
N4—Zn1—O1—C5 | −109.4 (1) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H18···O3i | 0.85 (3) | 1.91 (3) | 2.756 (2) | 176 (3) |
O2—H17···O4 | 0.84 (3) | 1.99 (3) | 2.789 (2) | 159 (4) |
Symmetry code: (i) x+1, y, z. |
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