Bis[(di-methyl-phosphor-yl)methan-amin-ium] tetra-chlorido-palladate(II).

In the crystal structure of the title compound, (C3H11NOP)2[PdCl4], (di-methyl-phosphor-yl)methanaminium (dpmaH(+)) cations are connected head-to-tail by strong N-H⋯O hydrogen bonds, forming inversion-related cyclic dimers. The square-planar [PdCl4](2-) counter-dianion is located about a center of inversion. The dications and the [PdCl4](2-) dianions are connected by medium-strong N-H⋯Cl hydrogen bonds, forming zigzag chains parallel to [001]. Somewhat weaker N-H⋯Cl hydrogen bonds connect the chains into a three-dimensional network.

Related literature

For transition metal complexes built by the neutral dpma ligand, see: Kochel (2009 ▶). For simple dpmaH+ salts, see: Reiss & Jörgens (2012 ▶); Buhl et al. (2013 ▶); Lambertz et al. (2013 ▶); Reiss (2013a ▶). For dpmaH+ metal complexes, see: Reiss (2013b ▶,c ▶,d ▶). For some structures and applications of tetra­chlorido­palladate(II) salts, see: Willett & Willett (1977 ▶); Hardacre et al. (2001 ▶); Lee et al. (2004 ▶); Song et al. (2012 ▶); Vranec et al. (2012 ▶); Serpell et al. (2013 ▶). For graph-set analysis, see: Grell et al. (2002 ▶).

Experimental

Crystal data

(C3H11NOP)2[PdCl4]

M = 464.39

Monoclinic,

a = 9.3600 (3) Å

b = 7.81198 (19) Å

c = 11.9892 (3) Å

β = 110.110 (3)°

V = 823.21 (4) Å3

Z = 2

Mo Kα radiation

μ = 1.96 mm−1

T = 290 K

0.18 × 0.12 × 0.11 mm

Data collection

Oxford Diffraction Xcalibur CCD diffractometer

Absorption correction: analytical [using a multifaceted crystal model (Clark & Reid, 1995 ▶)] T min = 0.764, T max = 0.850

26379 measured reflections

3595 independent reflections

3077 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.022

wR(F 2) = 0.051

S = 1.09

3595 reflections

94 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.46 e Å−3

Δρmin = −0.57 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO); data reduction: CrysAlis PRO); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2012 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813028067/wm2775sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813028067/wm2775Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

(C3H11NOP)2[PdCl4]	F(000) = 464
Mr = 464.39	Dx = 1.874 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.3600 (3) Å	Cell parameters from 12224 reflections
b = 7.81198 (19) Å	θ = 3.2–35.4°
c = 11.9892 (3) Å	µ = 1.96 mm−1
β = 110.110 (3)°	T = 290 K
V = 823.21 (4) Å3	Block, yellow
Z = 2	0.18 × 0.12 × 0.11 mm

Oxford Diffraction Xcalibur CCD diffractometer	3595 independent reflections
Radiation source: (Mo) X-ray Source	3077 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
Detector resolution: 16.2711 pixels mm-1	θmax = 35.0°, θmin = 3.2°
ω scans	h = −15→14
Absorption correction: analytical [using a multifaceted crystal model (Clark & Reid, 1995)]	k = −12→12
Tmin = 0.764, Tmax = 0.850	l = −19→19
26379 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.022	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.051	w = 1/[σ2(Fo2) + (0.0178P)2 + 0.217P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max = 0.007
3595 reflections	Δρmax = 0.46 e Å−3
94 parameters	Δρmin = −0.57 e Å−3
0 restraints	Extinction correction: SHELXL2013 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0040 (4)

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.

	x	y	z	Uiso*/Ueq
Pd1	0.0000	0.0000	0.0000	0.02259 (4)
Cl1	0.22877 (4)	0.04262 (5)	0.15119 (3)	0.03461 (8)
Cl2	0.07205 (5)	0.20056 (5)	−0.11116 (4)	0.03905 (9)
O1	0.13229 (12)	−0.01272 (13)	0.62240 (10)	0.0298 (2)
P1	0.21946 (4)	0.12971 (5)	0.59240 (3)	0.02481 (7)
N1	0.15898 (16)	−0.05812 (19)	0.38798 (13)	0.0316 (3)
H11	0.066 (3)	−0.046 (3)	0.384 (2)	0.056 (6)*
H12	0.167 (2)	−0.064 (3)	0.317 (2)	0.055 (6)*
H13	0.193 (2)	−0.151 (3)	0.421 (2)	0.049 (6)*
C1	0.1204 (2)	0.3284 (2)	0.57050 (18)	0.0448 (4)
H1A	0.0251	0.3174	0.5064	0.067*
H1B	0.1807	0.4155	0.5515	0.067*
H1C	0.1019	0.3595	0.6418	0.067*
C2	0.40239 (19)	0.1665 (2)	0.69942 (15)	0.0422 (4)
H2A	0.3919	0.2038	0.7725	0.063*
H2B	0.4538	0.2533	0.6708	0.063*
H2C	0.4604	0.0625	0.7128	0.063*
C3	0.25318 (18)	0.0838 (2)	0.45344 (14)	0.0348 (3)
H3A	0.2311	0.1854	0.4039	0.042*
H3B	0.3596	0.0555	0.4713	0.042*

	U11	U22	U33	U12	U13	U23
Pd1	0.02378 (7)	0.02169 (7)	0.02289 (7)	−0.00035 (5)	0.00878 (5)	−0.00143 (5)
Cl1	0.02834 (16)	0.0438 (2)	0.02818 (16)	−0.00517 (14)	0.00520 (13)	−0.00045 (14)
Cl2	0.0447 (2)	0.0374 (2)	0.03567 (19)	−0.00905 (16)	0.01464 (16)	0.00673 (15)
O1	0.0301 (5)	0.0308 (5)	0.0315 (5)	−0.0009 (4)	0.0142 (4)	0.0028 (4)
P1	0.02492 (16)	0.02507 (16)	0.02430 (15)	0.00067 (12)	0.00827 (12)	0.00136 (12)
N1	0.0337 (7)	0.0324 (6)	0.0328 (6)	−0.0007 (5)	0.0170 (5)	−0.0036 (5)
C1	0.0529 (10)	0.0314 (8)	0.0572 (11)	0.0111 (7)	0.0280 (9)	0.0087 (7)
C2	0.0354 (8)	0.0466 (10)	0.0369 (8)	−0.0086 (7)	0.0027 (6)	0.0016 (7)
C3	0.0358 (8)	0.0404 (8)	0.0336 (7)	−0.0094 (6)	0.0190 (6)	−0.0037 (6)

Pd1—Cl2i	2.3030 (4)	N1—H12	0.88 (2)
Pd1—Cl2	2.3030 (4)	N1—H13	0.84 (2)
Pd1—Cl1i	2.3049 (4)	C1—H1A	0.9600
Pd1—Cl1	2.3049 (4)	C1—H1B	0.9600
O1—P1	1.4951 (10)	C1—H1C	0.9600
P1—C2	1.7749 (16)	C2—H2A	0.9600
P1—C1	1.7809 (17)	C2—H2B	0.9600
P1—C3	1.8345 (15)	C2—H2C	0.9600
N1—C3	1.465 (2)	C3—H3A	0.9700
N1—H11	0.86 (2)	C3—H3B	0.9700
Cl2i—Pd1—Cl2	180.0	P1—C1—H1A	109.5
Cl2i—Pd1—Cl1i	88.803 (14)	P1—C1—H1B	109.5
Cl2—Pd1—Cl1i	91.196 (14)	H1A—C1—H1B	109.5
Cl2i—Pd1—Cl1	91.197 (14)	P1—C1—H1C	109.5
Cl2—Pd1—Cl1	88.803 (14)	H1A—C1—H1C	109.5
Cl1i—Pd1—Cl1	180.0	H1B—C1—H1C	109.5
O1—P1—C2	114.67 (7)	P1—C2—H2A	109.5
O1—P1—C1	112.61 (7)	P1—C2—H2B	109.5
C2—P1—C1	106.82 (9)	H2A—C2—H2B	109.5
O1—P1—C3	110.58 (7)	P1—C2—H2C	109.5
C2—P1—C3	105.30 (8)	H2A—C2—H2C	109.5
C1—P1—C3	106.27 (9)	H2B—C2—H2C	109.5
C3—N1—H11	111.1 (15)	N1—C3—P1	112.01 (10)
C3—N1—H12	108.8 (15)	N1—C3—H3A	109.2
H11—N1—H12	112 (2)	P1—C3—H3A	109.2
C3—N1—H13	110.2 (15)	N1—C3—H3B	109.2
H11—N1—H13	109 (2)	P1—C3—H3B	109.2
H12—N1—H13	106 (2)	H3A—C3—H3B	107.9
O1—P1—C3—N1	13.59 (14)	C1—P1—C3—N1	−108.92 (13)
C2—P1—C3—N1	137.98 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H12···Cl1	0.88 (2)	2.40 (2)	3.2220 (15)	155 (2)
N1—H11···O1ii	0.86 (2)	1.89 (2)	2.7425 (17)	172 (2)
N1—H13···Cl1iii	0.84 (2)	2.73 (2)	3.3752 (15)	135.1 (18)
N1—H13···Cl2iii	0.84 (2)	2.82 (2)	3.5241 (16)	143.4 (18)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H12⋯Cl1	0.88 (2)	2.40 (2)	3.2220 (15)	155 (2)
N1—H11⋯O1i	0.86 (2)	1.89 (2)	2.7425 (17)	172 (2)
N1—H13⋯Cl1ii	0.84 (2)	2.73 (2)	3.3752 (15)	135.1 (18)
N1—H13⋯Cl2ii	0.84 (2)	2.82 (2)	3.5241 (16)	143.4 (18)

Symmetry codes: (i) ; (ii) .