The title compound, [Pd
II(C
2O
4)(C
3H
10N
2)], crystallizes with two unique molecules in the asymmetric unit. The Pd
II atom adopts distorted
cis-square-planar geometry. The oxalate ligand lies in the coordination plane and the six-membered chelate ring formed by the Pd
II atom and the propane-1,3-diamine ligand adopts a chair conformation. The crystal packing is stabilized by a complex three-dimensional N—H
O hydrogen-bond network.
Supporting information
CCDC reference: 636809
Key indicators
- Single-crystal X-ray study
- T = 123 K
- Mean (C-C) = 0.004 Å
- R factor = 0.018
- wR factor = 0.038
- Data-to-parameter ratio = 17.2
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT369_ALERT_2_B Long C(sp2)-C(sp2) Bond C5 - C6 ... 1.57 Ang.
Alert level C
ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
Tmin and Tmax reported: 0.685 0.799
Tmin(prime) and Tmax expected: 0.794 0.799
RR(prime) = 0.863
Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.86
PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) . 1000 Ang.
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3
PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C9 - C10 ... 1.56 Ang.
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
5 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
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2005) and CRYSTALS
(Betteridge et al., 2003); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.
(Oxalato-
κ2O:
O')(propane-1,3-diamine-
κ2N:
N')palladium(II)
top
Crystal data top
[Pd(C2O4)(C3H10N2)] | F(000) = 1056.00 |
Mr = 268.57 | Dx = 2.180 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.7107 Å |
Hall symbol: -P 2ybc | Cell parameters from 13177 reflections |
a = 12.88 (1) Å | θ = 3.0–27.5° |
b = 10.49 (1) Å | µ = 2.25 mm−1 |
c = 13.59 (1) Å | T = 123 K |
β = 116.91 (3)° | Prism, brown |
V = 1637 (2) Å3 | 0.10 × 0.10 × 0.10 mm |
Z = 8 | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 2832 reflections with F2 > 2σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.033 |
ω scans | θmax = 27.5° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −15→16 |
Tmin = 0.685, Tmax = 0.799 | k = −13→13 |
15689 measured reflections | l = −17→16 |
3755 independent reflections | |
Refinement top
Refinement on F2 | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.018 | w = 1/[σ2(Fo2) + (0.0178P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.038 | (Δ/σ)max = 0.002 |
S = 0.91 | Δρmax = 0.46 e Å−3 |
3755 reflections | Δρmin = −0.45 e Å−3 |
218 parameters | |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement using all reflections. 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 | 0.596319 (13) | 0.478243 (18) | 0.345517 (14) | 0.01180 (5) | |
Pd2 | 0.882153 (13) | 0.237175 (18) | 0.160791 (13) | 0.01100 (5) | |
O1 | 0.65692 (12) | 0.53311 (17) | 0.50539 (13) | 0.0167 (4) | |
O2 | 0.82356 (13) | 0.60205 (18) | 0.64379 (13) | 0.0192 (4) | |
O3 | 0.76101 (12) | 0.51318 (17) | 0.37289 (13) | 0.0164 (4) | |
O4 | 0.91850 (13) | 0.61389 (18) | 0.49803 (13) | 0.0196 (4) | |
O5 | 0.84009 (12) | 0.25560 (17) | 0.00010 (12) | 0.0160 (4) | |
O6 | 0.69666 (13) | 0.33101 (17) | −0.15533 (13) | 0.0186 (4) | |
O7 | 0.71755 (12) | 0.30096 (17) | 0.11173 (13) | 0.0169 (4) | |
O8 | 0.56432 (13) | 0.36490 (19) | −0.04232 (14) | 0.0228 (4) | |
N1 | 0.42939 (15) | 0.4598 (2) | 0.32026 (16) | 0.0161 (4) | |
H1A | 0.4292 | 0.4615 | 0.3864 | 0.019* | |
H1B | 0.3892 | 0.5284 | 0.2822 | 0.019* | |
N2 | 0.55168 (15) | 0.4242 (2) | 0.18907 (16) | 0.0150 (4) | |
H2A | 0.5187 | 0.4917 | 0.1449 | 0.018* | |
H2B | 0.6176 | 0.4061 | 0.1844 | 0.018* | |
N3 | 1.04544 (15) | 0.1788 (2) | 0.19902 (15) | 0.0152 (4) | |
H3A | 1.0500 | 0.1646 | 0.1358 | 0.018* | |
H3B | 1.0950 | 0.2427 | 0.2346 | 0.018* | |
N4 | 0.91465 (15) | 0.2242 (2) | 0.31993 (15) | 0.0155 (4) | |
H4A | 0.9620 | 0.2888 | 0.3575 | 0.019* | |
H4B | 0.8472 | 0.2345 | 0.3237 | 0.019* | |
C1 | 0.3657 (2) | 0.3437 (3) | 0.2608 (2) | 0.0198 (5) | |
H1C | 0.2882 | 0.3438 | 0.2560 | 0.024* | |
H1D | 0.4063 | 0.2685 | 0.3017 | 0.024* | |
C2 | 0.35659 (19) | 0.3384 (3) | 0.1462 (2) | 0.0192 (5) | |
H2C | 0.3247 | 0.4185 | 0.1091 | 0.023* | |
H2D | 0.3024 | 0.2713 | 0.1050 | 0.023* | |
C3 | 0.47186 (18) | 0.3143 (3) | 0.1440 (2) | 0.0186 (5) | |
H3C | 0.5081 | 0.2388 | 0.1871 | 0.022* | |
H3D | 0.4578 | 0.2987 | 0.0686 | 0.022* | |
C6 | 0.76576 (18) | 0.5664 (2) | 0.54882 (19) | 0.0141 (5) | |
C5 | 0.82251 (18) | 0.5637 (2) | 0.46816 (19) | 0.0145 (5) | |
C4 | 1.08533 (19) | 0.0622 (3) | 0.26824 (19) | 0.0178 (5) | |
H6A | 1.1628 | 0.0396 | 0.2788 | 0.021* | |
H6B | 1.0335 | −0.0081 | 0.2305 | 0.021* | |
C7 | 1.08761 (19) | 0.0826 (3) | 0.38034 (19) | 0.0186 (5) | |
H7A | 1.1237 | 0.0090 | 0.4264 | 0.022* | |
H7B | 1.1359 | 0.1562 | 0.4154 | 0.022* | |
C8 | 0.9686 (2) | 0.1030 (2) | 0.37522 (19) | 0.0178 (5) | |
H8A | 0.9180 | 0.0327 | 0.3356 | 0.021* | |
H8B | 0.9762 | 0.1034 | 0.4496 | 0.021* | |
C9 | 0.73710 (18) | 0.3025 (2) | −0.05732 (19) | 0.0140 (5) | |
C10 | 0.66450 (18) | 0.3248 (2) | 0.00736 (19) | 0.0154 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Pd1 | 0.00969 (8) | 0.01378 (10) | 0.01064 (9) | −0.00070 (7) | 0.00346 (6) | −0.00029 (7) |
Pd2 | 0.01066 (8) | 0.01310 (10) | 0.00876 (9) | 0.00102 (6) | 0.00397 (6) | 0.00067 (7) |
O1 | 0.0134 (7) | 0.0229 (11) | 0.0143 (9) | −0.0022 (7) | 0.0067 (6) | −0.0009 (7) |
O2 | 0.0172 (8) | 0.0246 (11) | 0.0116 (9) | −0.0027 (7) | 0.0028 (7) | −0.0032 (8) |
O3 | 0.0125 (7) | 0.0223 (11) | 0.0139 (8) | −0.0024 (7) | 0.0055 (6) | −0.0036 (7) |
O4 | 0.0134 (8) | 0.0253 (11) | 0.0198 (9) | −0.0052 (7) | 0.0072 (7) | −0.0041 (8) |
O5 | 0.0147 (7) | 0.0207 (10) | 0.0117 (8) | 0.0037 (7) | 0.0053 (6) | 0.0010 (7) |
O6 | 0.0200 (8) | 0.0224 (11) | 0.0102 (9) | 0.0027 (7) | 0.0039 (7) | 0.0030 (7) |
O7 | 0.0142 (7) | 0.0246 (11) | 0.0125 (9) | 0.0039 (7) | 0.0066 (6) | 0.0015 (7) |
O8 | 0.0140 (8) | 0.0305 (12) | 0.0215 (10) | 0.0070 (7) | 0.0060 (7) | 0.0052 (8) |
N1 | 0.0144 (9) | 0.0194 (13) | 0.0139 (10) | 0.0000 (8) | 0.0057 (8) | −0.0016 (9) |
N2 | 0.0126 (9) | 0.0171 (12) | 0.0145 (10) | −0.0004 (8) | 0.0053 (8) | 0.0014 (9) |
N3 | 0.0143 (9) | 0.0196 (12) | 0.0115 (10) | 0.0002 (8) | 0.0057 (7) | −0.0004 (9) |
N4 | 0.0166 (9) | 0.0176 (12) | 0.0132 (10) | 0.0013 (8) | 0.0074 (8) | 0.0014 (9) |
C1 | 0.0175 (11) | 0.0194 (15) | 0.0228 (14) | −0.0049 (10) | 0.0094 (10) | −0.0021 (11) |
C2 | 0.0145 (11) | 0.0181 (15) | 0.0213 (14) | −0.0038 (9) | 0.0049 (10) | −0.0048 (11) |
C3 | 0.0182 (11) | 0.0179 (15) | 0.0170 (13) | −0.0029 (10) | 0.0055 (10) | −0.0061 (11) |
C6 | 0.0148 (10) | 0.0101 (13) | 0.0150 (13) | 0.0026 (9) | 0.0047 (9) | 0.0024 (10) |
C5 | 0.0141 (10) | 0.0124 (13) | 0.0153 (12) | 0.0011 (9) | 0.0052 (9) | 0.0019 (10) |
C4 | 0.0155 (11) | 0.0188 (15) | 0.0189 (13) | 0.0038 (9) | 0.0075 (9) | 0.0013 (10) |
C7 | 0.0196 (11) | 0.0159 (15) | 0.0151 (13) | 0.0042 (10) | 0.0033 (9) | 0.0035 (10) |
C8 | 0.0238 (12) | 0.0169 (15) | 0.0141 (13) | 0.0033 (10) | 0.0098 (10) | 0.0047 (10) |
C9 | 0.0160 (10) | 0.0116 (13) | 0.0127 (12) | −0.0028 (9) | 0.0049 (9) | −0.0033 (10) |
C10 | 0.0141 (11) | 0.0135 (14) | 0.0185 (13) | −0.0013 (9) | 0.0072 (10) | −0.0016 (10) |
Geometric parameters (Å, º) top
Pd1—N1 | 2.027 (2) | N3—H3A | 0.9000 |
Pd1—N2 | 2.017 (3) | N3—H3B | 0.9000 |
Pd2—N3 | 2.019 (2) | N4—C8 | 1.479 (3) |
Pd2—N4 | 2.013 (3) | N4—H4A | 0.9000 |
Pd1—O1 | 2.032 (2) | N4—H4B | 0.9000 |
Pd1—O3 | 2.014 (2) | C1—C2 | 1.510 (4) |
Pd2—O5 | 2.008 (2) | C1—H1C | 0.9700 |
Pd2—O7 | 2.026 (2) | C1—H1D | 0.9700 |
O1—C6 | 1.298 (3) | C2—C3 | 1.519 (3) |
O2—C6 | 1.221 (3) | C2—H2C | 0.9700 |
O3—C5 | 1.287 (3) | C2—H2D | 0.9700 |
O4—C5 | 1.231 (3) | C3—H3C | 0.9700 |
O5—C9 | 1.293 (3) | C3—H3D | 0.9700 |
O6—C9 | 1.228 (3) | C6—C5 | 1.569 (3) |
O7—C10 | 1.290 (3) | C4—C7 | 1.526 (3) |
O8—C10 | 1.228 (3) | C4—H6A | 0.9700 |
N1—C1 | 1.486 (3) | C4—H6B | 0.9700 |
N1—H1A | 0.9000 | C7—C8 | 1.517 (3) |
N1—H1B | 0.9000 | C7—H7A | 0.9700 |
N2—C3 | 1.480 (3) | C7—H7B | 0.9700 |
N2—H2A | 0.9000 | C8—H8A | 0.9700 |
N2—H2B | 0.9000 | C8—H8B | 0.9700 |
N3—C4 | 1.486 (3) | C9—C10 | 1.564 (3) |
| | | |
N1—Pd1—O1 | 94.17 (7) | C2—C1—H1D | 109.4 |
N2—Pd1—N1 | 91.16 (8) | H1C—C1—H1D | 108.0 |
N2—Pd1—O1 | 174.66 (6) | C1—C2—C3 | 113.9 (2) |
O3—Pd1—N1 | 174.92 (8) | C1—C2—H2C | 108.8 |
O3—Pd1—N2 | 91.13 (7) | C3—C2—H2C | 108.8 |
O3—Pd1—O1 | 83.58 (7) | C1—C2—H2D | 108.8 |
N3—Pd2—O7 | 175.72 (7) | C3—C2—H2D | 108.8 |
N4—Pd2—N3 | 90.98 (8) | H2C—C2—H2D | 107.7 |
N4—Pd2—O7 | 93.08 (7) | N2—C3—C2 | 111.3 (2) |
O5—Pd2—N3 | 92.63 (7) | N2—C3—H3C | 109.4 |
O5—Pd2—N4 | 176.34 (7) | C2—C3—H3C | 109.4 |
O5—Pd2—O7 | 83.29 (7) | N2—C3—H3D | 109.4 |
C6—O1—Pd1 | 112.06 (14) | C2—C3—H3D | 109.4 |
C5—O3—Pd1 | 112.19 (13) | H3C—C3—H3D | 108.0 |
C9—O5—Pd2 | 113.03 (14) | O2—C6—O1 | 125.4 (2) |
C10—O7—Pd2 | 112.35 (13) | O2—C6—C5 | 119.38 (19) |
C1—N1—Pd1 | 116.88 (14) | O1—C6—C5 | 115.2 (2) |
C1—N1—H1A | 108.1 | O4—C5—O3 | 125.2 (2) |
Pd1—N1—H1A | 108.1 | O4—C5—C6 | 118.5 (2) |
C1—N1—H1B | 108.1 | O3—C5—C6 | 116.21 (19) |
Pd1—N1—H1B | 108.1 | N3—C4—C7 | 111.2 (2) |
H1A—N1—H1B | 107.3 | N3—C4—H6A | 109.4 |
C3—N2—Pd1 | 117.95 (14) | C7—C4—H6A | 109.4 |
C3—N2—H2A | 107.8 | N3—C4—H6B | 109.4 |
Pd1—N2—H2A | 107.8 | C7—C4—H6B | 109.4 |
C3—N2—H2B | 107.8 | H6A—C4—H6B | 108.0 |
Pd1—N2—H2B | 107.8 | C8—C7—C4 | 114.3 (2) |
H2A—N2—H2B | 107.2 | C8—C7—H7A | 108.7 |
C4—N3—Pd2 | 115.72 (13) | C4—C7—H7A | 108.7 |
C4—N3—H3A | 108.4 | C8—C7—H7B | 108.7 |
Pd2—N3—H3A | 108.4 | C4—C7—H7B | 108.7 |
C4—N3—H3B | 108.4 | H7A—C7—H7B | 107.6 |
Pd2—N3—H3B | 108.4 | N4—C8—C7 | 112.12 (19) |
H3A—N3—H3B | 107.4 | N4—C8—H8A | 109.2 |
C8—N4—Pd2 | 115.17 (15) | C7—C8—H8A | 109.2 |
C8—N4—H4A | 108.5 | N4—C8—H8B | 109.2 |
Pd2—N4—H4A | 108.5 | C7—C8—H8B | 109.2 |
C8—N4—H4B | 108.5 | H8A—C8—H8B | 107.9 |
Pd2—N4—H4B | 108.5 | O6—C9—O5 | 124.3 (2) |
H4A—N4—H4B | 107.5 | O6—C9—C10 | 120.4 (2) |
N1—C1—C2 | 111.0 (2) | O5—C9—C10 | 115.4 (2) |
N1—C1—H1C | 109.4 | O8—C10—O7 | 124.9 (2) |
C2—C1—H1C | 109.4 | O8—C10—C9 | 119.2 (2) |
N1—C1—H1D | 109.4 | O7—C10—C9 | 115.82 (19) |
| | | |
Pd1—N1—C1—C2 | −61.1 (2) | O1—Pd1—N1—C1 | −135.21 (17) |
Pd1—N2—C3—C2 | 59.1 (2) | O3—Pd1—N2—C3 | 140.82 (17) |
N1—Pd1—N2—C3 | −43.72 (17) | O5—Pd2—N3—C4 | −131.30 (17) |
N1—C1—C2—C3 | 69.3 (3) | O7—Pd2—N4—C8 | 132.32 (15) |
N2—Pd1—N1—C1 | 44.44 (18) | Pd1—O1—C6—O2 | −179.3 (2) |
C1—C2—C3—N2 | −68.0 (3) | Pd1—O1—C6—C5 | 3.1 (2) |
Pd2—N3—C4—C7 | −61.9 (2) | Pd1—O3—C5—O4 | −167.0 (2) |
Pd2—N4—C8—C7 | 62.5 (2) | Pd1—O3—C5—C6 | 9.7 (3) |
N3—Pd2—N4—C8 | −49.04 (16) | O2—C6—C5—O4 | −9.8 (3) |
N3—C4—C7—C8 | 65.9 (3) | O1—C6—C5—O4 | 168.0 (2) |
N4—Pd2—N3—C4 | 49.28 (17) | O2—C6—C5—O3 | 173.3 (2) |
C4—C7—C8—N4 | −66.7 (3) | O1—C6—C5—O3 | −9.0 (3) |
O3—Pd1—O1—C6 | 1.44 (16) | Pd2—O5—C9—O6 | 174.2 (2) |
N1—Pd1—O1—C6 | −173.98 (17) | Pd2—O5—C9—C10 | −4.4 (3) |
N2—Pd1—O3—C5 | 174.27 (17) | Pd2—O7—C10—O8 | −179.7 (2) |
O1—Pd1—O3—C5 | −6.50 (16) | Pd2—O7—C10—C9 | −1.0 (3) |
N3—Pd2—O5—C9 | −175.53 (17) | O6—C9—C10—O8 | 3.8 (4) |
O7—Pd2—O5—C9 | 3.14 (16) | O5—C9—C10—O8 | −177.5 (2) |
O5—Pd2—O7—C10 | −0.96 (16) | O6—C9—C10—O7 | −174.9 (2) |
N4—Pd2—O7—C10 | 178.55 (17) | O5—C9—C10—O7 | 3.8 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1i | 0.90 | 2.21 | 3.040 (3) | 154 |
N1—H1B···O6ii | 0.90 | 2.16 | 3.030 (3) | 164 |
N2—H2A···O8ii | 0.90 | 2.00 | 2.899 (4) | 176 |
N2—H2B···O7 | 0.90 | 2.24 | 3.061 (3) | 152 |
N3—H3A···O4iii | 0.90 | 2.10 | 2.997 (3) | 172 |
N3—H3B···O2iv | 0.90 | 2.22 | 3.071 (4) | 158 |
N4—H4A···O4iv | 0.90 | 2.13 | 2.968 (3) | 155 |
N4—H4B···O6v | 0.90 | 2.19 | 3.030 (3) | 155 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z; (iii) −x+2, y−1/2, −z+1/2; (iv) −x+2, −y+1, −z+1; (v) x, −y+1/2, z+1/2. |