(1,2-Benzene­diolato-κ²O,O′)(1,10-phenanthroline-κ²N,N′)­palladium(II) dihydrate

In the mononuclear catecholate complex, [Pd(C₆H₄O₂)(C₁₂H₈N₂)]·2H₂O, the Pd^II 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.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](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

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Computing details

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.

(I)

Crystal data

[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) Å^3	0.50 × 0.20 × 0.20 mm
Z = 4

Data collection

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

Refinement on F^2	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.026	w = 1/[σ^2(Fo^2) + (0.034P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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···O3^i	2.772 (3)	C3···C17^vii	3.565 (4)
O1···O4^ii	2.907 (3)	C3···C13^vii	3.568 (4)
O3···C1^i	3.293 (3)	C4···C10^vi	3.393 (4)
O3···C12^iii	3.535 (4)	C4···C16^i	3.417 (4)
O3···C13^i	3.549 (3)	C4···C9^vi	3.543 (4)
O4···C8^iv	3.284 (4)	C5···C16^i	3.345 (4)
O4···C11^iv	3.485 (4)	C5···C15^i	3.533 (4)
O4···C13^v	3.600 (4)	C5···C8^vi	3.569 (4)
N1···C8^vi	3.332 (4)	C5···C9^vi	3.575 (4)
N1···C17^i	3.568 (4)	C6···C15^i	3.426 (4)
C1···C8^vi	3.520 (4)	C6···C6^vi	3.431 (5)
C2···C9^vi	3.577 (4)	C8···C8^iv	3.557 (5)
C3···C18^vii	3.469 (4)	C10···C16^viii	3.591 (4)
C3···C9^vi	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)

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···O1^i	0.76	2.04	2.772 (3)	163
O4—H4B···O1^v	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.