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In the mononuclear catecholate complex, [Pd(C6H4O2)(C12H8N2)]·2H2O, the PdII has a distorted cis square-planar four-coordinate geometry. It is bonded to two O atoms of a bidentate catecholate dianion and two N atoms of the bidentate phenanthroline. The overall conformation of the complex including catechol and phenanthroline rings is almost planar.
Supporting information
CCDC reference: 225684
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.004 Å
- R factor = 0.026
- wR factor = 0.071
- Data-to-parameter ratio = 16.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Pd1 - N1 = 5.37 su
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 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
Data collection: MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1992); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation & Rigaku Corporation, 2000); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.
Crystal data top
[Pd(C6H4O2)(C12H8N2)]·2H2O | F(000) = 864.0 |
Mr = 430.75 | Dx = 1.746 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.7107 Å |
Hall symbol: -P 2yn | Cell parameters from 25 reflections |
a = 9.248 (2) Å | θ = 14.7–15.0° |
b = 16.462 (2) Å | µ = 1.16 mm−1 |
c = 10.802 (1) Å | T = 296 K |
β = 94.70 (1)° | Plate, dark red |
V = 1639.0 (4) Å3 | 0.50 × 0.20 × 0.20 mm |
Z = 4 | |
Data collection top
Rigaku AFC-5R diffractometer | Rint = 0.042 |
ω–2θ scans | θmax = 27.5° |
Absorption correction: ψ scan (North et al., 1968) | h = 0→12 |
Tmin = 0.757, Tmax = 0.793 | k = 0→21 |
4127 measured reflections | l = −14→13 |
3760 independent reflections | 3 standard reflections every 150 reflections |
3021 reflections with I > 2.0σ(I) | intensity decay: 0.7% |
Refinement top
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.026 | w = 1/[σ2(Fo2) + (0.034P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.071 | (Δ/σ)max = 0.003 |
S = 1.13 | Δρmax = 0.37 e Å−3 |
3760 reflections | Δρmin = −0.66 e Å−3 |
226 parameters | |
Special details top
Refinement. Refinement using reflections with F2 > -10.0 σ(F2). The
weighted R-factor (wR) and goodness of fit (S) are based
on F2. R-factor (gt) are based on F. The threshold
expression of F2 > 2.0 σ(F2) is used only for calculating
R-factor (gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Pd1 | −0.06586 (2) | 0.97227 (1) | 0.68957 (2) | 0.03041 (7) | |
O1 | −0.2289 (2) | 0.9672 (1) | 0.5578 (2) | 0.0392 (4) | |
O2 | 0.0017 (2) | 0.8711 (1) | 0.6135 (2) | 0.0420 (4) | |
O3 | 0.2951 (2) | 0.8869 (1) | 0.5620 (2) | 0.0514 (5) | |
O4 | 0.5476 (2) | 0.9208 (2) | 0.7183 (2) | 0.0752 (7) | |
N1 | −0.1230 (2) | 1.0772 (1) | 0.7691 (2) | 0.0336 (4) | |
N2 | 0.0970 (2) | 0.9787 (1) | 0.8233 (2) | 0.0316 (4) | |
C1 | −0.2389 (3) | 1.1246 (2) | 0.7425 (2) | 0.0414 (6) | |
C2 | −0.2577 (3) | 1.1975 (2) | 0.8045 (3) | 0.0483 (7) | |
C3 | −0.1560 (3) | 1.2233 (2) | 0.8946 (3) | 0.0459 (7) | |
C4 | −0.0335 (3) | 1.1746 (2) | 0.9267 (2) | 0.0386 (6) | |
C5 | −0.0230 (3) | 1.1019 (1) | 0.8613 (2) | 0.0325 (5) | |
C6 | 0.0956 (3) | 1.0481 (2) | 0.8918 (2) | 0.0317 (5) | |
C7 | 0.2003 (3) | 1.0662 (2) | 0.9879 (2) | 0.0362 (5) | |
C8 | 0.3104 (3) | 1.0083 (2) | 1.0147 (3) | 0.0422 (6) | |
C9 | 0.3105 (3) | 0.9392 (2) | 0.9457 (3) | 0.0449 (6) | |
C10 | 0.2024 (3) | 0.9248 (2) | 0.8508 (3) | 0.0391 (6) | |
C11 | 0.1886 (3) | 1.1421 (2) | 1.0528 (3) | 0.0443 (6) | |
C12 | 0.0784 (3) | 1.1936 (2) | 1.0219 (3) | 0.0473 (7) | |
C13 | −0.2049 (3) | 0.9047 (2) | 0.4790 (2) | 0.0387 (6) | |
C14 | −0.2975 (4) | 0.8891 (2) | 0.3744 (3) | 0.0508 (7) | |
C15 | −0.2686 (4) | 0.8236 (2) | 0.2975 (3) | 0.0615 (9) | |
C16 | −0.1487 (4) | 0.7754 (2) | 0.3253 (3) | 0.0598 (9) | |
C17 | −0.0558 (4) | 0.7903 (2) | 0.4307 (3) | 0.0505 (7) | |
C18 | −0.0829 (3) | 0.8551 (2) | 0.5091 (2) | 0.0390 (6) | |
H1 | −0.3089 | 1.1083 | 0.6808 | 0.0497* | |
H2 | −0.3401 | 1.2288 | 0.7845 | 0.0579* | |
H3 | −0.1676 | 1.2726 | 0.9345 | 0.0551* | |
H3A | 0.2175 | 0.8744 | 0.5746 | 0.0618* | |
H3B | 0.2815 | 0.9307 | 0.5433 | 0.0618* | |
H4A | 0.4794 | 0.9139 | 0.6757 | 0.0895* | |
H4B | 0.6033 | 0.9306 | 0.6722 | 0.0895* | |
H8 | 0.3822 | 1.0172 | 1.0787 | 0.0506* | |
H9 | 0.3836 | 0.9010 | 0.9622 | 0.0539* | |
H10 | 0.2038 | 0.8767 | 0.8057 | 0.0470* | |
H11 | 0.2580 | 1.1557 | 1.1167 | 0.0532* | |
H12 | 0.0748 | 1.2428 | 1.0637 | 0.0568* | |
H14 | −0.3782 | 0.9218 | 0.3554 | 0.0610* | |
H15 | −0.3307 | 0.8126 | 0.2274 | 0.0738* | |
H16 | −0.1296 | 0.7324 | 0.2731 | 0.0717* | |
H17 | 0.0245 | 0.7571 | 0.4490 | 0.0606* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Pd1 | 0.0322 (1) | 0.0287 (1) | 0.0306 (1) | −0.00060 (7) | 0.00398 (7) | −0.00222 (7) |
O1 | 0.041 (1) | 0.039 (1) | 0.0369 (10) | −0.0008 (8) | −0.0017 (8) | −0.0043 (8) |
O2 | 0.041 (1) | 0.0351 (10) | 0.051 (1) | 0.0014 (8) | 0.0048 (8) | −0.0110 (8) |
O3 | 0.044 (1) | 0.057 (1) | 0.053 (1) | 0.0020 (9) | −0.0006 (9) | 0.006 (1) |
O4 | 0.048 (1) | 0.128 (2) | 0.049 (1) | −0.015 (1) | 0.000 (1) | −0.007 (1) |
N1 | 0.037 (1) | 0.035 (1) | 0.0290 (10) | 0.0033 (9) | 0.0048 (8) | 0.0015 (8) |
N2 | 0.031 (1) | 0.032 (1) | 0.032 (1) | 0.0004 (8) | 0.0048 (8) | −0.0007 (8) |
C1 | 0.046 (1) | 0.047 (2) | 0.032 (1) | 0.012 (1) | 0.001 (1) | 0.004 (1) |
C2 | 0.058 (2) | 0.045 (2) | 0.043 (2) | 0.021 (1) | 0.009 (1) | 0.008 (1) |
C3 | 0.064 (2) | 0.035 (1) | 0.040 (1) | 0.010 (1) | 0.015 (1) | −0.003 (1) |
C4 | 0.050 (2) | 0.032 (1) | 0.035 (1) | 0.000 (1) | 0.011 (1) | −0.001 (1) |
C5 | 0.036 (1) | 0.033 (1) | 0.030 (1) | −0.0020 (10) | 0.0089 (10) | 0.0013 (9) |
C6 | 0.032 (1) | 0.031 (1) | 0.033 (1) | −0.0046 (10) | 0.0084 (10) | 0.0017 (10) |
C7 | 0.035 (1) | 0.043 (1) | 0.032 (1) | −0.009 (1) | 0.007 (1) | 0.002 (1) |
C8 | 0.030 (1) | 0.058 (2) | 0.039 (1) | −0.006 (1) | 0.003 (1) | 0.003 (1) |
C9 | 0.035 (1) | 0.055 (2) | 0.045 (2) | 0.009 (1) | 0.006 (1) | 0.006 (1) |
C10 | 0.038 (1) | 0.038 (1) | 0.042 (1) | 0.007 (1) | 0.008 (1) | 0.002 (1) |
C11 | 0.044 (1) | 0.050 (2) | 0.038 (1) | −0.010 (1) | 0.001 (1) | −0.009 (1) |
C12 | 0.065 (2) | 0.039 (1) | 0.039 (1) | −0.009 (1) | 0.009 (1) | −0.012 (1) |
C13 | 0.045 (1) | 0.037 (1) | 0.034 (1) | −0.014 (1) | 0.008 (1) | −0.001 (1) |
C14 | 0.059 (2) | 0.054 (2) | 0.039 (2) | −0.018 (1) | 0.001 (1) | 0.003 (1) |
C15 | 0.080 (2) | 0.066 (2) | 0.038 (2) | −0.037 (2) | 0.006 (2) | −0.007 (1) |
C16 | 0.087 (2) | 0.049 (2) | 0.046 (2) | −0.029 (2) | 0.028 (2) | −0.016 (1) |
C17 | 0.062 (2) | 0.036 (1) | 0.057 (2) | −0.013 (1) | 0.024 (1) | −0.010 (1) |
C18 | 0.046 (1) | 0.033 (1) | 0.039 (1) | −0.013 (1) | 0.015 (1) | −0.004 (1) |
Geometric parameters (Å, º) top
PD1—O1 | 1.989 (2) | C5—C6 | 1.427 (3) |
PD1—O2 | 1.981 (2) | C6—C7 | 1.392 (3) |
PD1—N1 | 2.019 (2) | C7—C8 | 1.408 (4) |
PD1—N2 | 2.003 (2) | C7—C11 | 1.442 (4) |
O1—C13 | 1.365 (3) | C8—C9 | 1.360 (4) |
O2—C18 | 1.344 (3) | C8—H8 | 0.93 |
O3—H3A | 0.77 | C9—C10 | 1.392 (4) |
O3—H3B | 0.76 | C9—H9 | 0.93 |
O4—H4A | 0.76 | C10—H10 | 0.93 |
O4—H4B | 0.76 | C11—C12 | 1.346 (4) |
N1—C1 | 1.337 (3) | C11—H11 | 0.93 |
N1—C5 | 1.365 (3) | C12—H12 | 0.93 |
N2—C6 | 1.362 (3) | C13—C14 | 1.385 (4) |
N2—C10 | 1.333 (3) | C13—C18 | 1.409 (4) |
C1—C2 | 1.393 (4) | C14—C15 | 1.400 (5) |
C1—H1 | 0.93 | C14—H14 | 0.93 |
C2—C3 | 1.364 (4) | C15—C16 | 1.377 (5) |
C2—H2 | 0.93 | C15—H15 | 0.93 |
C3—C4 | 1.408 (4) | C16—C17 | 1.390 (4) |
C3—H3 | 0.93 | C16—H16 | 0.93 |
C4—C5 | 1.398 (4) | C17—C18 | 1.398 (4) |
C4—C12 | 1.433 (4) | C17—H17 | 0.93 |
| | | |
O1···O3i | 2.772 (3) | C3···C17vii | 3.565 (4) |
O1···O4ii | 2.907 (3) | C3···C13vii | 3.568 (4) |
O3···C1i | 3.293 (3) | C4···C10vi | 3.393 (4) |
O3···C12iii | 3.535 (4) | C4···C16i | 3.417 (4) |
O3···C13i | 3.549 (3) | C4···C9vi | 3.543 (4) |
O4···C8iv | 3.284 (4) | C5···C16i | 3.345 (4) |
O4···C11iv | 3.485 (4) | C5···C15i | 3.533 (4) |
O4···C13v | 3.600 (4) | C5···C8vi | 3.569 (4) |
N1···C8vi | 3.332 (4) | C5···C9vi | 3.575 (4) |
N1···C17i | 3.568 (4) | C6···C15i | 3.426 (4) |
C1···C8vi | 3.520 (4) | C6···C6vi | 3.431 (5) |
C2···C9vi | 3.577 (4) | C8···C8iv | 3.557 (5) |
C3···C18vii | 3.469 (4) | C10···C16viii | 3.591 (4) |
C3···C9vi | 3.546 (4) | | |
| | | |
O1—PD1—O2 | 85.09 (7) | C6—C7—C11 | 118.2 (2) |
O1—PD1—N1 | 97.51 (7) | C8—C7—C11 | 124.6 (2) |
O1—PD1—N2 | 179.19 (8) | C7—C8—C9 | 119.1 (2) |
O2—PD1—N1 | 176.80 (8) | C7—C8—H8 | 120.5 |
O2—PD1—N2 | 95.72 (8) | C9—C8—H8 | 120.5 |
N1—PD1—N2 | 81.69 (8) | C8—C9—C10 | 120.9 (3) |
PD1—O1—C13 | 109.0 (1) | C8—C9—H9 | 119.5 |
PD1—O2—C18 | 109.3 (1) | C10—C9—H9 | 119.5 |
H3A—O3—H3B | 99.5 | N2—C10—C9 | 121.2 (2) |
H4A—O4—H4B | 102.0 | N2—C10—H10 | 119.4 |
PD1—N1—C1 | 129.8 (2) | C9—C10—H10 | 119.4 |
PD1—N1—C5 | 112.3 (2) | C7—C11—C12 | 120.6 (2) |
C1—N1—C5 | 117.8 (2) | C7—C11—H11 | 119.7 |
PD1—N2—C6 | 113.3 (2) | C12—C11—H11 | 119.7 |
PD1—N2—C10 | 128.2 (2) | C4—C12—C11 | 121.9 (3) |
C6—N2—C10 | 118.5 (2) | C4—C12—H12 | 119.0 |
N1—C1—C2 | 121.9 (2) | C11—C12—H12 | 119.0 |
N1—C1—H1 | 119.0 | O1—C13—C14 | 121.9 (2) |
C2—C1—H1 | 119.0 | O1—C13—C18 | 117.4 (2) |
C1—C2—C3 | 120.3 (3) | C14—C13—C18 | 120.7 (3) |
C1—C2—H2 | 119.8 | C13—C14—C15 | 119.5 (3) |
C3—C2—H2 | 119.8 | C13—C14—H14 | 120.2 |
C2—C3—C4 | 119.5 (3) | C15—C14—H14 | 120.2 |
C2—C3—H3 | 120.2 | C14—C15—C16 | 120.2 (3) |
C4—C3—H3 | 120.2 | C14—C15—H15 | 119.9 |
C3—C4—C5 | 116.8 (2) | C16—C15—H15 | 119.9 |
C3—C4—C12 | 124.9 (2) | C15—C16—C17 | 120.6 (3) |
C5—C4—C12 | 118.2 (2) | C15—C16—H16 | 119.7 |
N1—C5—C4 | 123.6 (2) | C17—C16—H16 | 119.7 |
N1—C5—C6 | 116.5 (2) | C16—C17—C18 | 120.1 (3) |
C4—C5—C6 | 119.9 (2) | C16—C17—H17 | 119.9 |
N2—C6—C5 | 115.9 (2) | C18—C17—H17 | 119.9 |
N2—C6—C7 | 123.2 (2) | O2—C18—C13 | 118.7 (2) |
C5—C6—C7 | 120.9 (2) | O2—C18—C17 | 122.5 (2) |
C6—C7—C8 | 117.1 (2) | C13—C18—C17 | 118.8 (2) |
| | | |
PD1—O1—C13—C14 | −176.8 (2) | N2—C6—C7—C8 | −1.0 (4) |
PD1—O1—C13—C18 | 4.4 (3) | N2—C6—C7—C11 | 179.1 (2) |
PD1—O2—C18—C13 | −5.5 (3) | N2—C10—C9—C8 | 1.0 (4) |
PD1—O2—C18—C17 | 175.7 (2) | C1—N1—C5—C4 | −1.7 (4) |
PD1—N1—C1—C2 | −177.2 (2) | C1—N1—C5—C6 | 176.9 (2) |
PD1—N1—C5—C4 | 176.8 (2) | C1—C2—C3—C4 | −1.6 (4) |
PD1—N1—C5—C6 | −4.6 (3) | C2—C1—N1—C5 | 0.9 (4) |
PD1—N2—C6—C5 | 2.7 (3) | C2—C3—C4—C5 | 0.9 (4) |
PD1—N2—C6—C7 | −178.6 (2) | C2—C3—C4—C12 | −178.0 (3) |
PD1—N2—C10—C9 | 178.6 (2) | C3—C4—C5—C6 | −177.8 (2) |
O1—PD1—O2—C18 | 6.1 (2) | C3—C4—C12—C11 | 176.1 (3) |
O1—PD1—N1—C1 | 2.8 (2) | C4—C5—C6—C7 | 1.2 (4) |
O1—PD1—N1—C5 | −175.4 (2) | C4—C12—C11—C7 | 1.8 (4) |
O1—C13—C14—C15 | −179.2 (3) | C5—C4—C12—C11 | −2.7 (4) |
O1—C13—C18—O2 | 0.8 (4) | C5—C6—N2—C10 | −177.6 (2) |
O1—C13—C18—C17 | 179.6 (2) | C5—C6—C7—C8 | 177.7 (2) |
O2—PD1—O1—C13 | −5.7 (2) | C5—C6—C7—C11 | −2.2 (4) |
O2—PD1—N2—C6 | 174.1 (2) | C6—N2—C10—C9 | −1.1 (4) |
O2—PD1—N2—C10 | −5.6 (2) | C6—C5—C4—C12 | 1.2 (4) |
O2—C18—C13—C14 | −178.1 (3) | C6—C7—C8—C9 | 0.9 (4) |
O2—C18—C17—C16 | 178.5 (3) | C6—C7—C11—C12 | 0.7 (4) |
N1—PD1—O1—C13 | 172.4 (2) | C7—C6—N2—C10 | 1.2 (4) |
N1—PD1—N2—C6 | −4.0 (2) | C7—C8—C9—C10 | −0.9 (4) |
N1—PD1—N2—C10 | 176.3 (2) | C8—C7—C11—C12 | −179.1 (3) |
N1—C1—C2—C3 | 0.7 (4) | C9—C8—C7—C11 | −179.3 (3) |
N1—C5—C4—C3 | 0.8 (4) | C13—C14—C15—C16 | −0.3 (5) |
N1—C5—C4—C12 | 179.8 (2) | C13—C18—C17—C16 | −0.3 (4) |
N1—C5—C6—N2 | 1.3 (3) | C14—C13—C18—C17 | 0.8 (4) |
N1—C5—C6—C7 | −177.4 (2) | C14—C15—C16—C17 | 0.8 (5) |
N2—PD1—O2—C18 | −174.0 (2) | C15—C14—C13—C18 | −0.5 (4) |
N2—PD1—N1—C1 | −177.1 (2) | C15—C16—C17—C18 | −0.5 (5) |
N2—PD1—N1—C5 | 4.7 (2) | C15—C16—C17—C18 | −0.5 (5) |
N2—C6—C5—C4 | −180.0 (2) | | |
Symmetry codes: (i) −x, −y+2, −z+1; (ii) x−1, y, z; (iii) −x+1/2, y−1/2, −z+3/2; (iv) −x+1, −y+2, −z+2; (v) x+1, y, z; (vi) −x, −y+2, −z+2; (vii) −x−1/2, y+1/2, −z+3/2; (viii) x+1/2, −y+3/2, z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3A···O2 | 0.77 | 2.07 | 2.826 (3) | 166 |
O3—H3B···O1i | 0.76 | 2.04 | 2.772 (3) | 163 |
O4—H4B···O1v | 0.76 | 2.15 | 2.907 (3) | 174 |
O4—H4A···O3 | 0.76 | 2.07 | 2.823 (3) | 176 |
Symmetry codes: (i) −x, −y+2, −z+1; (v) x+1, y, z. |
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