Chloro­[2-(N,N-dimethyl­amino)ethanol-κN][2-(N,N-dimethyl­amino)ethano­lato-κ²N,O]palladium(II)

In the title compound, [Pd(C₄H₁₀NO)Cl(C₄H₁₁NO)], the geometry around the Pd atom, which is coordinated by one O, one Cl and two N atoms, is square-planar, with the N atoms trans to each other. One deprotonated N,N-dimethyl­amino­ethanol (dmaeH) mol­ecule acts as a bidentate ligand, while the other is coordinated through the N atom only. The structure displays O—H...O hydrogen bonding.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.036
• wR factor = 0.091
• Data-to-parameter ratio = 22.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.89
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.62

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 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
   1 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

---

Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Chloro[2(N,N-dimethylamino)ethanol-κN][2-(N,N-dimethylamino)ethanolato- κ²N,O]palladium(II)

Crystal data

[Pd(C4H10NO)Cl(C4H11NO)]	F(000) = 1296
Mr = 319.12	Dx = 1.756 Mg m^−3
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 8173 reflections
a = 15.571 (2) Å	θ = 2.6–30.6°
b = 18.482 (3) Å	µ = 1.74 mm^−1
c = 8.3885 (12) Å	T = 100 K
V = 2414.1 (6) Å^3	Block, brown
Z = 8	0.43 × 0.29 × 0.27 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2988 independent reflections
Radiation source: fine-focus sealed tube	2571 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
ω scans	θmax = 28.3°, θmin = 1.7°
Absorption correction: multi-scan (SADABS in SAINT-Plus; Bruker, 2003)	h = −20→20
Tmin = 0.426, Tmax = 0.625	k = −24→23
22210 measured reflections	l = −11→11

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.092	H-atom parameters constrained
S = 1.19	w = 1/[σ^2(Fo^2) + (0.0369P)^2 + 6.6811P] where P = (Fo^2 + 2Fc^2)/3
2988 reflections	(Δ/σ)max = 0.001
132 parameters	Δρmax = 1.70 e Å^−3
0 restraints	Δρmin = −0.65 e Å^−3

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 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Pd1	0.488472 (16)	0.619254 (13)	0.22256 (3)	0.01169 (10)
Cl1	0.41766 (6)	0.64150 (5)	0.46262 (10)	0.01932 (19)
N1	0.60767 (19)	0.61226 (15)	0.3377 (4)	0.0132 (6)
N2	0.37498 (18)	0.62251 (15)	0.0954 (4)	0.0148 (6)
O2	0.54327 (16)	0.60199 (13)	0.0109 (3)	0.0154 (5)
C6	0.4800 (2)	0.5846 (2)	−0.1048 (4)	0.0198 (7)
H6A	0.4649	0.5327	−0.0973	0.024*
H6B	0.5025	0.5941	−0.2131	0.024*
C4	0.6795 (2)	0.5925 (2)	0.2291 (4)	0.0176 (7)
H4A	0.7334	0.5914	0.2893	0.026*
H4B	0.6839	0.6284	0.1435	0.026*
H4C	0.6686	0.5447	0.1829	0.026*
C3	0.6275 (2)	0.68247 (18)	0.4183 (4)	0.0156 (7)
H3A	0.6856	0.6797	0.4660	0.019*
H3B	0.5859	0.6903	0.5059	0.019*
C7	0.4015 (2)	0.6303 (2)	−0.0748 (4)	0.0196 (7)
H7A	0.4145	0.6817	−0.0982	0.023*
H7B	0.3542	0.6147	−0.1456	0.023*
C2	0.6239 (3)	0.7465 (2)	0.3050 (4)	0.0210 (8)
H2A	0.6584	0.7359	0.2087	0.025*
H2B	0.5638	0.7549	0.2713	0.025*
C5	0.6044 (2)	0.5545 (2)	0.4624 (4)	0.0196 (7)
H5A	0.5906	0.5081	0.4123	0.029*
H5B	0.5602	0.5666	0.5411	0.029*
H5C	0.6603	0.5511	0.5154	0.029*
C9	0.3163 (2)	0.6832 (2)	0.1354 (5)	0.0217 (8)
H9A	0.2648	0.6804	0.0684	0.033*
H9B	0.3456	0.7293	0.1163	0.033*
H9C	0.2997	0.6800	0.2479	0.033*
C8	0.3288 (2)	0.5532 (2)	0.1211 (5)	0.0211 (8)
H8A	0.3144	0.5482	0.2343	0.032*
H8B	0.3655	0.5128	0.0883	0.032*
H8C	0.2759	0.5529	0.0576	0.032*
O4	0.65618 (17)	0.80926 (14)	0.3807 (4)	0.0226 (6)
H4	0.6152	0.8331	0.4193	0.034*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pd1	0.01019 (14)	0.01117 (14)	0.01370 (15)	0.00008 (9)	0.00022 (9)	−0.00029 (9)
Cl1	0.0177 (4)	0.0221 (4)	0.0181 (4)	0.0027 (3)	0.0041 (3)	−0.0012 (3)
N1	0.0133 (14)	0.0114 (13)	0.0149 (14)	0.0007 (10)	−0.0006 (11)	−0.0016 (10)
N2	0.0107 (13)	0.0131 (13)	0.0207 (15)	0.0006 (11)	−0.0021 (11)	0.0000 (11)
O2	0.0143 (12)	0.0183 (12)	0.0135 (12)	−0.0017 (9)	0.0002 (9)	−0.0018 (9)
C6	0.0152 (17)	0.026 (2)	0.0182 (17)	−0.0001 (15)	−0.0023 (13)	−0.0017 (14)
C4	0.0133 (16)	0.0187 (17)	0.0207 (18)	0.0032 (13)	−0.0007 (13)	−0.0031 (14)
C3	0.0138 (16)	0.0166 (17)	0.0164 (16)	−0.0005 (13)	−0.0014 (13)	−0.0043 (13)
C7	0.0166 (17)	0.0234 (19)	0.0187 (17)	0.0000 (14)	−0.0026 (13)	0.0030 (14)
C2	0.026 (2)	0.0122 (16)	0.0248 (19)	−0.0019 (14)	−0.0022 (15)	−0.0021 (14)
C5	0.0192 (18)	0.0179 (18)	0.0216 (18)	0.0004 (14)	−0.0026 (14)	0.0063 (14)
C9	0.0134 (17)	0.0192 (19)	0.032 (2)	0.0047 (14)	−0.0030 (14)	−0.0006 (15)
C8	0.0156 (18)	0.0181 (18)	0.030 (2)	−0.0047 (14)	−0.0018 (14)	0.0000 (15)
O4	0.0163 (13)	0.0154 (13)	0.0360 (16)	−0.0013 (10)	0.0036 (11)	−0.0069 (11)

Geometric parameters (Å, º)

Pd1—O2	1.996 (2)	C3—H3A	0.9900
Pd1—N2	2.065 (3)	C3—H3B	0.9900
Pd1—N1	2.096 (3)	C7—H7A	0.9900
Pd1—Cl1	2.3324 (9)	C7—H7B	0.9900
N1—C4	1.489 (4)	C2—O4	1.414 (4)
N1—C5	1.495 (4)	C2—H2A	0.9900
N1—C3	1.495 (4)	C2—H2B	0.9900
N2—C8	1.485 (4)	C5—H5A	0.9800
N2—C9	1.486 (4)	C5—H5B	0.9800
N2—C7	1.493 (5)	C5—H5C	0.9800
O2—C6	1.420 (4)	C9—H9A	0.9800
C6—C7	1.507 (5)	C9—H9B	0.9800
C6—H6A	0.9900	C9—H9C	0.9800
C6—H6B	0.9900	C8—H8A	0.9800
C4—H4A	0.9800	C8—H8B	0.9800
C4—H4B	0.9800	C8—H8C	0.9800
C4—H4C	0.9800	O4—H4	0.8400
C3—C2	1.520 (5)
O2—Pd1—N2	84.89 (11)	N1—C3—H3B	109.1
O2—Pd1—N1	91.24 (11)	C2—C3—H3B	109.1
N2—Pd1—N1	175.93 (12)	H3A—C3—H3B	107.8
O2—Pd1—Cl1	176.86 (8)	N2—C7—C6	109.2 (3)
N2—Pd1—Cl1	92.09 (9)	N2—C7—H7A	109.8
N1—Pd1—Cl1	91.81 (8)	C6—C7—H7A	109.8
C4—N1—C5	106.2 (3)	N2—C7—H7B	109.8
C4—N1—C3	109.5 (3)	C6—C7—H7B	109.8
C5—N1—C3	108.1 (3)	H7A—C7—H7B	108.3
C4—N1—Pd1	113.5 (2)	O4—C2—C3	110.2 (3)
C5—N1—Pd1	109.7 (2)	O4—C2—H2A	109.6
C3—N1—Pd1	109.7 (2)	C3—C2—H2A	109.6
C8—N2—C9	108.7 (3)	O4—C2—H2B	109.6
C8—N2—C7	110.9 (3)	C3—C2—H2B	109.6
C9—N2—C7	108.2 (3)	H2A—C2—H2B	108.1
C8—N2—Pd1	108.3 (2)	N1—C5—H5A	109.5
C9—N2—Pd1	115.6 (2)	N1—C5—H5B	109.5
C7—N2—Pd1	105.1 (2)	H5A—C5—H5B	109.5
C6—O2—Pd1	110.3 (2)	N1—C5—H5C	109.5
O2—C6—C7	108.8 (3)	H5A—C5—H5C	109.5
O2—C6—H6A	109.9	H5B—C5—H5C	109.5
C7—C6—H6A	109.9	N2—C9—H9A	109.5
O2—C6—H6B	109.9	N2—C9—H9B	109.5
C7—C6—H6B	109.9	H9A—C9—H9B	109.5
H6A—C6—H6B	108.3	N2—C9—H9C	109.5
N1—C4—H4A	109.5	H9A—C9—H9C	109.5
N1—C4—H4B	109.5	H9B—C9—H9C	109.5
H4A—C4—H4B	109.5	N2—C8—H8A	109.5
N1—C4—H4C	109.5	N2—C8—H8B	109.5
H4A—C4—H4C	109.5	H8A—C8—H8B	109.5
H4B—C4—H4C	109.5	N2—C8—H8C	109.5
N1—C3—C2	112.7 (3)	H8A—C8—H8C	109.5
N1—C3—H3A	109.1	H8B—C8—H8C	109.5
C2—C3—H3A	109.1	C2—O4—H4	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O2^i	0.84	1.81	2.641 (4)	169

Symmetry code: (i) x, −y+3/2, z+1/2.