(Oxalato-κ²O,O′)(propane-1,3-diamine-κ²N,N′)palladium(II)

The title compound, [Pd^II(C₂O₄)(C₃H₁₀N₂)], 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.

Key indicators

• Single-crystal X-ray study
• T = 123 K
• Mean [sigma](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

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Computing details

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)

Crystal data

[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) Å^3	0.10 × 0.10 × 0.10 mm
Z = 8

Data collection

Rigaku R-AXIS RAPID diffractometer	2832 reflections with F^2 > 2σ(F^2)
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

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.018	w = 1/[σ^2(Fo^2) + (0.0178P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 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

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 (Ų)

	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 (Ų)

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

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)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1^i	0.90	2.21	3.040 (3)	154
N1—H1B···O6^ii	0.90	2.16	3.030 (3)	164
N2—H2A···O8^ii	0.90	2.00	2.899 (4)	176
N2—H2B···O7	0.90	2.24	3.061 (3)	152
N3—H3A···O4^iii	0.90	2.10	2.997 (3)	172
N3—H3B···O2^iv	0.90	2.22	3.071 (4)	158
N4—H4A···O4^iv	0.90	2.13	2.968 (3)	155
N4—H4B···O6^v	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.