{[1-(2-Amino-ethyl-amino)-1-methyl-ethyl]phospho-nato-κN,N',O}chloridopalladium(II) monohydrate.

In the title compound, [Pd(C(5)H(14)N(2)O(3)P)Cl]·H(2)O, the Pd(II) atom shows a slightly distorted square-planar geometry and forms two five-membered metallacycles, which both exhibit half-chair conformations. The crystal structure consists of layers propogating in the [100] direction which are connected into a three-dimensional network by strong N-H⋯Cl, N-H⋯O and O-H⋯O hydrogen bonds.

Related literature

For general background to the use of organic phospho­nic acids as chelating agents in metal extraction and as drugs for the prevention of calcification and bone resorption, see: Matczak-Jon & Videnova-Adrabinska (2005 ▶); Tromelin et al. (1986 ▶); Szabo et al. (2002 ▶). For related structures, see: Shkol’nikova et al. (1991 ▶).

Experimental

Crystal data

[Pd(C5H14N2O3P)Cl]·H2O

M = 341.02

Triclinic,

a = 7.2158 (2) Å

b = 7.8981 (2) Å

c = 10.3179 (3) Å

α = 97.968 (2)°

β = 98.403 (2)°

γ = 95.894 (2)°

V = 571.55 (3) Å3

Z = 2

Mo Kα radiation

μ = 1.99 mm−1

T = 100 K

0.38 × 0.12 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.519, T max = 0.832

8452 measured reflections

2306 independent reflections

1954 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.076

S = 1.05

2306 reflections

147 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.75 e Å−3

Δρmin = −0.55 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810001765/im2173sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810001765/im2173Isup2.hkl

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

[Pd(C5H14N2O3P)Cl]·H2O	Z = 2
Mr = 341.02	F(000) = 340
Triclinic, P1	Dx = 1.982 Mg m−3
Hall symbol: -P 1	Melting point: 535 K
a = 7.2158 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.8981 (2) Å	Cell parameters from 2725 reflections
c = 10.3179 (3) Å	θ = 2.9–26.2°
α = 97.968 (2)°	µ = 1.99 mm−1
β = 98.403 (2)°	T = 100 K
γ = 95.894 (2)°	Block, yellow
V = 571.55 (3) Å3	0.38 × 0.12 × 0.10 mm

Bruker APEXII CCD diffractometer	2306 independent reflections
Radiation source: fine-focus sealed tube	1954 reflections with I > 2σ(I)
graphite	Rint = 0.046
Detector resolution: 8.26 pixels mm-1	θmax = 26.4°, θmin = 2.0°
φ and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −9→9
Tmin = 0.519, Tmax = 0.832	l = −12→12
8452 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0351P)2 + 0.6204P] where P = (Fo2 + 2Fc2)/3
2306 reflections	(Δ/σ)max < 0.001
147 parameters	Δρmax = 0.75 e Å−3
1 restraint	Δρmin = −0.55 e Å−3

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 of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Pd1	0.22708 (4)	0.52397 (4)	0.07010 (3)	0.01203 (11)
P1	0.15753 (15)	0.54887 (16)	0.35047 (10)	0.0162 (3)
Cl1	0.27656 (14)	0.26896 (14)	−0.05111 (10)	0.0155 (2)
N1	0.1808 (5)	0.7519 (4)	0.1696 (3)	0.0120 (7)
H1N	0.060 (7)	0.746 (6)	0.150 (4)	0.014*
N2	0.2614 (5)	0.6578 (5)	−0.0782 (3)	0.0126 (7)
H21N	0.199 (6)	0.594 (6)	−0.161 (4)	0.015*
H22N	0.368 (7)	0.665 (6)	−0.078 (4)	0.015*
O1	0.2068 (4)	0.4194 (4)	0.2400 (3)	0.0184 (7)
O2	0.2368 (4)	0.5237 (4)	0.4882 (3)	0.0209 (7)
O3	−0.0616 (4)	0.5451 (4)	0.3289 (3)	0.0190 (7)
H3O	−0.117 (6)	0.538 (7)	0.387 (4)	0.023*
O4	0.5268 (5)	0.2409 (5)	0.2944 (3)	0.0249 (8)
H41O	0.577 (8)	0.316 (7)	0.351 (5)	0.030*
H42O	0.428 (8)	0.276 (7)	0.281 (5)	0.030*
C1	0.2460 (6)	0.7633 (6)	0.3169 (4)	0.0158 (9)
C2	0.4630 (6)	0.7880 (6)	0.3480 (4)	0.0214 (10)
H2A	0.5114	0.9015	0.3301	0.032*
H2B	0.5122	0.6982	0.2921	0.032*
H2C	0.5036	0.7801	0.4416	0.032*
C3	0.1618 (7)	0.9064 (6)	0.3944 (4)	0.0237 (10)
H3A	0.2125	1.0182	0.3746	0.036*
H3B	0.1944	0.9037	0.4896	0.036*
H3C	0.0241	0.8895	0.3688	0.036*
C4	0.2573 (6)	0.8907 (5)	0.1007 (4)	0.0157 (9)
H4A	0.3965	0.9126	0.1242	0.019*
H4B	0.2044	0.9989	0.1265	0.019*
C5	0.2000 (6)	0.8285 (6)	−0.0464 (4)	0.0168 (9)
H5A	0.0613	0.8209	−0.0712	0.020*
H5B	0.2596	0.9106	−0.0970	0.020*

	U11	U22	U33	U12	U13	U23
Pd1	0.01212 (17)	0.01164 (19)	0.01225 (17)	0.00112 (12)	0.00298 (11)	0.00076 (12)
P1	0.0142 (5)	0.0219 (7)	0.0118 (5)	−0.0005 (5)	0.0022 (4)	0.0023 (5)
Cl1	0.0142 (5)	0.0136 (6)	0.0183 (5)	0.0028 (4)	0.0027 (4)	0.0002 (4)
N1	0.0102 (17)	0.0102 (19)	0.0140 (17)	−0.0012 (15)	−0.0016 (13)	0.0022 (14)
N2	0.0097 (17)	0.013 (2)	0.0143 (18)	0.0005 (15)	0.0019 (14)	0.0013 (15)
O1	0.0237 (16)	0.0159 (17)	0.0148 (15)	−0.0016 (13)	0.0046 (12)	0.0013 (13)
O2	0.0154 (15)	0.033 (2)	0.0141 (15)	−0.0006 (14)	0.0034 (12)	0.0062 (14)
O3	0.0129 (15)	0.0294 (19)	0.0147 (15)	−0.0011 (14)	0.0034 (11)	0.0047 (14)
O4	0.0216 (18)	0.027 (2)	0.0244 (18)	0.0028 (16)	0.0009 (14)	−0.0003 (15)
C1	0.018 (2)	0.016 (2)	0.012 (2)	0.0002 (18)	0.0018 (16)	0.0017 (17)
C2	0.020 (2)	0.028 (3)	0.014 (2)	−0.003 (2)	0.0005 (17)	0.004 (2)
C3	0.027 (3)	0.023 (3)	0.019 (2)	0.003 (2)	0.0066 (19)	−0.004 (2)
C4	0.018 (2)	0.009 (2)	0.020 (2)	0.0005 (18)	0.0020 (17)	0.0024 (18)
C5	0.013 (2)	0.014 (2)	0.024 (2)	0.0019 (18)	0.0033 (17)	0.0062 (19)

Pd1—N2	2.006 (3)	O4—H41O	0.79 (5)
Pd1—N1	2.029 (3)	O4—H42O	0.79 (6)
Pd1—O1	2.056 (3)	C1—C3	1.523 (6)
Pd1—Cl1	2.3083 (11)	C1—C2	1.538 (6)
P1—O2	1.500 (3)	C2—H2A	0.9800
P1—O1	1.530 (3)	C2—H2B	0.9800
P1—O3	1.561 (3)	C2—H2C	0.9800
P1—C1	1.844 (4)	C3—H3A	0.9800
N1—C4	1.490 (5)	C3—H3B	0.9800
N1—C1	1.511 (5)	C3—H3C	0.9800
N1—H1N	0.86 (5)	C4—C5	1.511 (6)
N2—C5	1.471 (5)	C4—H4A	0.9900
N2—H21N	0.96 (5)	C4—H4B	0.9900
N2—H22N	0.76 (5)	C5—H5A	0.9900
O3—H3O	0.77 (3)	C5—H5B	0.9900
N2—Pd1—N1	84.95 (14)	C3—C1—C2	111.8 (4)
N2—Pd1—O1	171.76 (13)	N1—C1—P1	103.1 (3)
N1—Pd1—O1	87.95 (12)	C3—C1—P1	111.8 (3)
N2—Pd1—Cl1	92.89 (11)	C2—C1—P1	108.9 (3)
N1—Pd1—Cl1	177.67 (10)	C1—C2—H2A	109.5
O1—Pd1—Cl1	94.26 (9)	C1—C2—H2B	109.5
O2—P1—O1	114.59 (18)	H2A—C2—H2B	109.5
O2—P1—O3	112.56 (16)	C1—C2—H2C	109.5
O1—P1—O3	107.83 (17)	H2A—C2—H2C	109.5
O2—P1—C1	111.12 (19)	H2B—C2—H2C	109.5
O1—P1—C1	105.66 (18)	C1—C3—H3A	109.5
O3—P1—C1	104.36 (19)	C1—C3—H3B	109.5
C4—N1—C1	118.5 (3)	H3A—C3—H3B	109.5
C4—N1—Pd1	107.3 (2)	C1—C3—H3C	109.5
C1—N1—Pd1	110.9 (3)	H3A—C3—H3C	109.5
C4—N1—H1N	105 (3)	H3B—C3—H3C	109.5
C1—N1—H1N	112 (3)	N1—C4—C5	106.8 (3)
Pd1—N1—H1N	101 (3)	N1—C4—H4A	110.4
C5—N2—Pd1	108.9 (2)	C5—C4—H4A	110.4
C5—N2—H21N	114 (3)	N1—C4—H4B	110.4
Pd1—N2—H21N	111 (3)	C5—C4—H4B	110.4
C5—N2—H22N	111 (4)	H4A—C4—H4B	108.6
Pd1—N2—H22N	103 (3)	N2—C5—C4	108.7 (3)
H21N—N2—H22N	109 (4)	N2—C5—H5A	109.9
P1—O1—Pd1	112.20 (17)	C4—C5—H5A	109.9
P1—O3—H3O	121 (4)	N2—C5—H5B	109.9
H41O—O4—H42O	97 (5)	C4—C5—H5B	109.9
N1—C1—C3	110.7 (3)	H5A—C5—H5B	108.3
N1—C1—C2	110.2 (3)
N2—Pd1—N1—C4	−18.0 (3)	C4—N1—C1—P1	−168.6 (3)
O1—Pd1—N1—C4	157.8 (3)	Pd1—N1—C1—P1	−43.9 (3)
N2—Pd1—N1—C1	−148.9 (3)	O2—P1—C1—N1	170.2 (2)
O1—Pd1—N1—C1	26.9 (3)	O1—P1—C1—N1	45.4 (3)
N1—Pd1—N2—C5	−10.8 (3)	O3—P1—C1—N1	−68.2 (3)
Cl1—Pd1—N2—C5	168.3 (3)	O2—P1—C1—C3	−70.8 (3)
O2—P1—O1—Pd1	−149.06 (16)	O1—P1—C1—C3	164.3 (3)
O3—P1—O1—Pd1	84.75 (19)	O3—P1—C1—C3	50.7 (3)
C1—P1—O1—Pd1	−26.4 (2)	O2—P1—C1—C2	53.2 (3)
N1—Pd1—O1—P1	3.43 (18)	O1—P1—C1—C2	−71.6 (3)
Cl1—Pd1—O1—P1	−175.86 (15)	O3—P1—C1—C2	174.8 (3)
C4—N1—C1—C3	71.7 (5)	C1—N1—C4—C5	168.9 (3)
Pd1—N1—C1—C3	−163.6 (3)	Pd1—N1—C4—C5	42.4 (4)
C4—N1—C1—C2	−52.6 (5)	Pd1—N2—C5—C4	37.5 (4)
Pd1—N1—C1—C2	72.2 (4)	N1—C4—C5—N2	−53.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···Cl1i	0.86 (5)	2.48 (5)	3.326 (4)	169 (4)
N2—H21N···O3i	0.96 (5)	1.98 (5)	2.937 (5)	177 (4)
N2—H22N···Cl1ii	0.76 (5)	2.68 (5)	3.365 (4)	151 (4)
O3—H3O···O2iii	0.77 (3)	1.75 (3)	2.509 (4)	168 (6)
O4—H41O···O2iv	0.79 (5)	2.14 (6)	2.911 (5)	166 (5)
O4—H42O···O1	0.79 (6)	2.08 (6)	2.854 (5)	167 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯Cl1i	0.86 (5)	2.48 (5)	3.326 (4)	169 (4)
N2—H21N⋯O3i	0.96 (5)	1.98 (5)	2.937 (5)	177 (4)
N2—H22N⋯Cl1ii	0.76 (5)	2.68 (5)	3.365 (4)	151 (4)
O3—H3O⋯O2iii	0.77 (3)	1.75 (3)	2.509 (4)	168 (6)
O4—H41O⋯O2iv	0.79 (5)	2.14 (6)	2.911 (5)	166 (5)
O4—H42O⋯O1	0.79 (6)	2.08 (6)	2.854 (5)	167 (5)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .