Di-chlorido-(4,4'-di-tert-butyl-2,2'-bi-pyridine-κ(2) N,N')palladium(II) dimethyl sulfoxide monosolvate monohydrate.

The title compound, [PdCl2(C18H24N2)]·(CH3)2SO·H2O, the Pd(II) ion is in a distorted square-planar geometry. The Pd-N bond distances are 2.022 (2) and 2.027 (2) Å, the Pd-Cl bond distances are 2.2880 (7) and 2.2833 (7) Å, and the ligand bite angle is 80.07 (9)°. The dimethyl sulfoxide and water mol-ecules form linear chains along [100] by O-H⋯O and O-H⋯S hydrogen bonds, generating eight- and 12-membered rings. C-H⋯Cl inter-actions link the chains, forming a three-dimensional arrangement. In addition, the 4,4-di-tert-butyl-2,2'-bi-pyridine ligand exhibits π-π stacking inter-actions [centroid-centroid distances = 3.8741 (15) and 3.8353 (15) Å]. The DMSO solvent is disordered and was refined with an occupancy ratio of 0.866 (3):0.134 (3).

Related literature

For compounds with N—N ligands, see: Corona-Rodríguez et al. (2007 ▶); Basauri-Molina et al. (2010 ▶). For the crystal structure of non-solvated compound, see: Qin et al. (2002 ▶); MacLean et al. (2002 ▶). For metallomacrocycles, see: Qin et al. (2002 ▶); Tzeng et al. (2001 ▶). For similar compounds and their crystal structures, see: Jones et al. (2007 ▶).

Experimental

Crystal data

[PdCl2(C18H24N2)]·C2H6OS·H2O

M = 541.83

Monoclinic,

a = 7.4869 (3) Å

b = 19.5052 (8) Å

c = 16.8538 (7) Å

β = 102.907 (1)°

V = 2399.03 (17) Å3

Z = 4

Mo Kα radiation

μ = 1.10 mm−1

T = 298 K

0.42 × 0.19 × 0.09 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: analytical (SADABS; Sheldrick, 2008 ▶) T min = 0.780, T max = 0.932

13351 measured reflections

4343 independent reflections

3766 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.076

S = 1.01

4343 reflections

302 parameters

118 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.39 e Å−3

Δρmin = −0.55 e Å−3

Data collection: APEX2 (Bruker, 2012 ▶); cell refinement: SAINT (Bruker, 2012 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814009453/pj2010sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814009453/pj2010Isup2.hkl

Additional supporting information: crystallographic information; 3D view; checkCIF report

[PdCl2(C18H24N2)]·C2H6OS·H2O	F(000) = 1112
Mr = 541.83	Dx = 1.500 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.4869 (3) Å	Cell parameters from 9545 reflections
b = 19.5052 (8) Å	θ = 2.4–25.3°
c = 16.8538 (7) Å	µ = 1.10 mm−1
β = 102.907 (1)°	T = 298 K
V = 2399.03 (17) Å3	Prism, yellow
Z = 4	0.42 × 0.19 × 0.09 mm

Bruker APEXII CCD area-detector diffractometer	3766 reflections with I > 2σ(I)
Detector resolution: 0.83 pixels mm-1	Rint = 0.030
ω scans	θmax = 25.3°, θmin = 2.1°
Absorption correction: analytical (SADABS; Sheldrick, 2008)	h = −9→8
Tmin = 0.780, Tmax = 0.932	k = −22→23
13351 measured reflections	l = −20→17
4343 independent reflections

Refinement on F2	118 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.076	w = 1/[σ2(Fo2) + (0.042P)2 + 0.5P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.002
4343 reflections	Δρmax = 0.39 e Å−3
302 parameters	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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Pd1	0.23053 (3)	0.61408 (2)	0.50569 (2)	0.02992 (9)
Cl1	0.06474 (11)	0.69947 (4)	0.42999 (5)	0.0527 (2)
Cl2	0.38522 (12)	0.69340 (4)	0.59479 (5)	0.0573 (2)
N1	0.3456 (3)	0.53217 (10)	0.57115 (12)	0.0297 (5)
C2	0.3043 (3)	0.47048 (12)	0.53503 (14)	0.0282 (5)
C3	0.3586 (3)	0.40999 (13)	0.57591 (15)	0.0325 (6)
H3	0.3309	0.3684	0.5490	0.039*
C4	0.4548 (3)	0.41033 (14)	0.65727 (15)	0.0342 (6)
C5	0.4957 (4)	0.47497 (14)	0.69216 (16)	0.0378 (6)
H5	0.5611	0.4783	0.7459	0.045*
C6	0.4416 (4)	0.53308 (14)	0.64896 (15)	0.0373 (6)
H6	0.4721	0.5752	0.6741	0.045*
N7	0.1298 (3)	0.53767 (10)	0.42684 (12)	0.0296 (5)
C8	0.1932 (3)	0.47392 (12)	0.45083 (14)	0.0274 (5)
C9	0.1545 (3)	0.41861 (13)	0.39897 (15)	0.0337 (6)
H9	0.1980	0.3755	0.4173	0.040*
C10	0.0514 (3)	0.42587 (13)	0.31945 (15)	0.0333 (6)
C11	−0.0115 (4)	0.49177 (14)	0.29707 (15)	0.0375 (6)
H11	−0.0813	0.4996	0.2449	0.045*
C12	0.0281 (3)	0.54553 (13)	0.35099 (15)	0.0358 (6)
H12	−0.0171	0.5888	0.3343	0.043*
C13	0.5026 (4)	0.34551 (14)	0.70770 (17)	0.0407 (6)
C14	0.3815 (5)	0.34392 (17)	0.7700 (2)	0.0599 (9)
H14A	0.4021	0.3846	0.8028	0.072*
H14B	0.4114	0.3043	0.8043	0.072*
H14C	0.2550	0.3418	0.7420	0.072*
C15	0.7021 (4)	0.34643 (18)	0.7528 (2)	0.0623 (9)
H15A	0.7790	0.3444	0.7142	0.075*
H15B	0.7266	0.3076	0.7885	0.075*
H15C	0.7270	0.3879	0.7840	0.075*
C16	0.4686 (5)	0.28042 (15)	0.6560 (2)	0.0601 (9)
H16A	0.3408	0.2772	0.6303	0.072*
H16B	0.5042	0.2411	0.6901	0.072*
H16C	0.5394	0.2821	0.6150	0.072*
C17	0.0188 (4)	0.36691 (14)	0.25874 (17)	0.0419 (7)
C18	−0.1755 (5)	0.36822 (19)	0.2081 (2)	0.0730 (11)
H18A	−0.2600	0.3662	0.2433	0.088*
H18B	−0.1948	0.3295	0.1720	0.088*
H18C	−0.1951	0.4098	0.1768	0.088*
C19	0.1540 (6)	0.3743 (2)	0.2040 (2)	0.0750 (12)
H19A	0.1374	0.4181	0.1774	0.090*
H19B	0.1331	0.3386	0.1638	0.090*
H19C	0.2768	0.3709	0.2362	0.090*
C20	0.0506 (5)	0.29733 (16)	0.3010 (2)	0.0643 (10)
H20A	0.1775	0.2929	0.3277	0.077*
H20B	0.0180	0.2615	0.2613	0.077*
H20C	−0.0237	0.2938	0.3404	0.077*
S1	0.13101 (19)	0.11340 (6)	0.41808 (7)	0.0740 (4)	0.866 (3)
O1	0.2143 (7)	0.0432 (3)	0.4267 (4)	0.1113 (14)	0.866 (3)
C21	−0.0510 (7)	0.1118 (3)	0.4701 (4)	0.0994 (19)	0.866 (3)
H21A	−0.1488	0.0837	0.4405	0.119*	0.866 (3)
H21B	−0.0951	0.1576	0.4742	0.119*	0.866 (3)
H21C	−0.0074	0.0933	0.5237	0.119*	0.866 (3)
C22	0.2808 (10)	0.1680 (3)	0.4875 (4)	0.112 (2)	0.866 (3)
H22A	0.3915	0.1751	0.4688	0.135*	0.866 (3)
H22B	0.3099	0.1469	0.5404	0.135*	0.866 (3)
H22C	0.2219	0.2112	0.4908	0.135*	0.866 (3)
S1A	0.2169 (17)	0.0735 (7)	0.4816 (7)	0.114 (3)	0.134 (3)
O1A	0.258 (4)	0.0344 (17)	0.411 (2)	0.113 (5)	0.134 (3)
C21A	−0.028 (2)	0.0783 (19)	0.463 (2)	0.094 (5)	0.134 (3)
H21D	−0.0771	0.0334	0.4678	0.112*	0.134 (3)
H21E	−0.0754	0.0953	0.4086	0.112*	0.134 (3)
H21F	−0.0628	0.1086	0.5015	0.112*	0.134 (3)
C22A	0.252 (5)	0.1620 (9)	0.462 (3)	0.107 (6)	0.134 (3)
H22D	0.3807	0.1706	0.4682	0.128*	0.134 (3)
H22E	0.2053	0.1899	0.4996	0.128*	0.134 (3)
H22F	0.1890	0.1730	0.4073	0.128*	0.134 (3)
O2	0.4246 (8)	1.0021 (3)	0.5968 (3)	0.1554 (16)
H2A	0.522 (6)	0.990 (4)	0.580 (4)	0.187*
H2B	0.377 (10)	1.015 (4)	0.5472 (18)	0.187*

	U11	U22	U33	U12	U13	U23
Pd1	0.03419 (14)	0.02250 (12)	0.03379 (13)	−0.00049 (8)	0.00909 (9)	−0.00093 (7)
Cl1	0.0637 (5)	0.0305 (4)	0.0592 (5)	0.0118 (3)	0.0034 (4)	0.0048 (3)
Cl2	0.0757 (6)	0.0323 (4)	0.0567 (5)	−0.0099 (4)	−0.0007 (4)	−0.0110 (3)
N1	0.0307 (11)	0.0271 (11)	0.0323 (11)	−0.0022 (9)	0.0088 (9)	−0.0002 (9)
C2	0.0255 (12)	0.0305 (13)	0.0293 (12)	−0.0005 (10)	0.0076 (10)	0.0003 (10)
C3	0.0354 (14)	0.0260 (13)	0.0362 (14)	0.0010 (11)	0.0085 (12)	0.0021 (11)
C4	0.0300 (14)	0.0382 (14)	0.0352 (14)	0.0019 (11)	0.0088 (11)	0.0066 (12)
C5	0.0376 (15)	0.0417 (16)	0.0307 (13)	−0.0020 (12)	0.0005 (12)	0.0037 (12)
C6	0.0420 (16)	0.0359 (15)	0.0322 (13)	−0.0025 (12)	0.0043 (12)	−0.0019 (11)
N7	0.0322 (11)	0.0267 (11)	0.0311 (11)	−0.0001 (9)	0.0097 (9)	0.0005 (9)
C8	0.0264 (13)	0.0269 (13)	0.0299 (12)	−0.0012 (10)	0.0086 (10)	0.0026 (10)
C9	0.0381 (15)	0.0271 (13)	0.0363 (14)	−0.0003 (11)	0.0094 (12)	−0.0007 (11)
C10	0.0297 (14)	0.0356 (15)	0.0355 (13)	−0.0055 (11)	0.0088 (11)	−0.0029 (11)
C11	0.0370 (15)	0.0424 (16)	0.0294 (13)	−0.0016 (12)	−0.0007 (12)	0.0018 (12)
C12	0.0361 (15)	0.0314 (14)	0.0383 (14)	0.0022 (11)	0.0051 (12)	0.0067 (11)
C13	0.0383 (15)	0.0392 (16)	0.0434 (16)	0.0051 (13)	0.0068 (13)	0.0109 (13)
C14	0.066 (2)	0.057 (2)	0.062 (2)	0.0104 (17)	0.0274 (18)	0.0289 (17)
C15	0.0480 (19)	0.062 (2)	0.071 (2)	0.0108 (17)	−0.0007 (17)	0.0235 (18)
C16	0.068 (2)	0.0397 (17)	0.068 (2)	0.0097 (16)	0.0046 (18)	0.0151 (16)
C17	0.0435 (17)	0.0425 (16)	0.0383 (15)	−0.0064 (13)	0.0059 (13)	−0.0109 (13)
C18	0.060 (2)	0.064 (2)	0.080 (3)	−0.0053 (18)	−0.015 (2)	−0.031 (2)
C19	0.089 (3)	0.083 (3)	0.062 (2)	−0.026 (2)	0.037 (2)	−0.036 (2)
C20	0.083 (3)	0.0400 (18)	0.066 (2)	−0.0046 (17)	0.010 (2)	−0.0193 (16)
S1	0.0947 (10)	0.0791 (9)	0.0486 (6)	−0.0027 (6)	0.0171 (6)	−0.0019 (5)
O1	0.129 (4)	0.086 (2)	0.125 (4)	0.013 (2)	0.040 (3)	−0.020 (3)
C21	0.108 (4)	0.129 (6)	0.065 (3)	0.002 (3)	0.026 (3)	−0.006 (4)
C22	0.144 (5)	0.115 (4)	0.078 (4)	−0.035 (4)	0.024 (4)	−0.025 (3)
S1A	0.138 (5)	0.114 (6)	0.085 (5)	−0.003 (5)	0.010 (5)	0.002 (5)
O1A	0.123 (10)	0.108 (9)	0.104 (10)	0.005 (10)	0.015 (9)	−0.005 (8)
C21A	0.135 (6)	0.085 (11)	0.058 (10)	0.006 (8)	0.016 (9)	0.010 (11)
C22A	0.140 (11)	0.113 (7)	0.066 (12)	−0.012 (9)	0.020 (11)	−0.009 (9)
O2	0.173 (5)	0.174 (4)	0.126 (3)	0.025 (4)	0.047 (3)	0.023 (3)

Pd1—N1	2.022 (2)	C16—H16B	0.9600
Pd1—N7	2.027 (2)	C16—H16C	0.9600
Pd1—Cl2	2.2833 (7)	C17—C18	1.513 (4)
Pd1—Cl1	2.2880 (7)	C17—C19	1.522 (4)
N1—C6	1.347 (3)	C17—C20	1.526 (4)
N1—C2	1.353 (3)	C18—H18A	0.9600
C2—C3	1.381 (3)	C18—H18B	0.9600
C2—C8	1.477 (3)	C18—H18C	0.9600
C3—C4	1.399 (3)	C19—H19A	0.9600
C3—H3	0.9300	C19—H19B	0.9600
C4—C5	1.396 (4)	C19—H19C	0.9600
C4—C13	1.521 (4)	C20—H20A	0.9600
C5—C6	1.359 (4)	C20—H20B	0.9600
C5—H5	0.9300	C20—H20C	0.9600
C6—H6	0.9300	S1—O1	1.498 (5)
N7—C12	1.342 (3)	S1—C21	1.777 (5)
N7—C8	1.360 (3)	S1—C22	1.782 (5)
C8—C9	1.378 (3)	C21—H21A	0.9600
C9—C10	1.396 (3)	C21—H21B	0.9600
C9—H9	0.9300	C21—H21C	0.9600
C10—C11	1.392 (4)	C22—H22A	0.9600
C10—C17	1.522 (4)	C22—H22B	0.9600
C11—C12	1.376 (4)	C22—H22C	0.9600
C11—H11	0.9300	S1A—O1A	1.504 (12)
C12—H12	0.9300	S1A—C22A	1.789 (9)
C13—C15	1.517 (4)	S1A—C21A	1.792 (9)
C13—C16	1.529 (4)	C21A—H21D	0.9600
C13—C14	1.534 (4)	C21A—H21E	0.9600
C14—H14A	0.9600	C21A—H21F	0.9600
C14—H14B	0.9600	C22A—H22D	0.9600
C14—H14C	0.9600	C22A—H22E	0.9600
C15—H15A	0.9600	C22A—H22F	0.9600
C15—H15B	0.9600	O2—H2A	0.869 (10)
C15—H15C	0.9600	O2—H2B	0.867 (10)
C16—H16A	0.9600
N1—Pd1—N7	80.07 (9)	C13—C16—H16B	109.5
N1—Pd1—Cl2	94.87 (6)	H16A—C16—H16B	109.5
N7—Pd1—Cl2	171.60 (6)	C13—C16—H16C	109.5
N1—Pd1—Cl1	172.53 (6)	H16A—C16—H16C	109.5
N7—Pd1—Cl1	95.37 (6)	H16B—C16—H16C	109.5
Cl2—Pd1—Cl1	90.33 (3)	C18—C17—C19	110.0 (3)
C6—N1—C2	117.9 (2)	C18—C17—C10	110.9 (2)
C6—N1—Pd1	126.19 (17)	C19—C17—C10	107.9 (2)
C2—N1—Pd1	115.51 (16)	C18—C17—C20	108.0 (3)
N1—C2—C3	121.5 (2)	C19—C17—C20	108.2 (3)
N1—C2—C8	114.5 (2)	C10—C17—C20	111.9 (2)
C3—C2—C8	123.9 (2)	C17—C18—H18A	109.5
C2—C3—C4	121.0 (2)	C17—C18—H18B	109.5
C2—C3—H3	119.5	H18A—C18—H18B	109.5
C4—C3—H3	119.5	C17—C18—H18C	109.5
C5—C4—C3	115.7 (2)	H18A—C18—H18C	109.5
C5—C4—C13	120.9 (2)	H18B—C18—H18C	109.5
C3—C4—C13	123.3 (2)	C17—C19—H19A	109.5
C6—C5—C4	121.1 (2)	C17—C19—H19B	109.5
C6—C5—H5	119.5	H19A—C19—H19B	109.5
C4—C5—H5	119.5	C17—C19—H19C	109.5
N1—C6—C5	122.7 (2)	H19A—C19—H19C	109.5
N1—C6—H6	118.6	H19B—C19—H19C	109.5
C5—C6—H6	118.6	C17—C20—H20A	109.5
C12—N7—C8	118.3 (2)	C17—C20—H20B	109.5
C12—N7—Pd1	126.10 (17)	H20A—C20—H20B	109.5
C8—N7—Pd1	115.04 (16)	C17—C20—H20C	109.5
N7—C8—C9	121.1 (2)	H20A—C20—H20C	109.5
N7—C8—C2	114.3 (2)	H20B—C20—H20C	109.5
C9—C8—C2	124.6 (2)	O1—S1—C21	106.5 (3)
C8—C9—C10	121.5 (2)	O1—S1—C22	107.1 (3)
C8—C9—H9	119.3	C21—S1—C22	97.2 (3)
C10—C9—H9	119.3	S1—C21—H21A	109.5
C11—C10—C9	115.8 (2)	S1—C21—H21B	109.5
C11—C10—C17	121.4 (2)	H21A—C21—H21B	109.5
C9—C10—C17	122.7 (2)	S1—C21—H21C	109.5
C12—C11—C10	121.0 (2)	H21A—C21—H21C	109.5
C12—C11—H11	119.5	H21B—C21—H21C	109.5
C10—C11—H11	119.5	S1—C22—H22A	109.5
N7—C12—C11	122.3 (2)	S1—C22—H22B	109.5
N7—C12—H12	118.8	H22A—C22—H22B	109.5
C11—C12—H12	118.8	S1—C22—H22C	109.5
C15—C13—C4	110.6 (2)	H22A—C22—H22C	109.5
C15—C13—C16	108.4 (3)	H22B—C22—H22C	109.5
C4—C13—C16	112.5 (2)	O1A—S1A—C22A	106.1 (8)
C15—C13—C14	108.9 (3)	O1A—S1A—C21A	105.7 (8)
C4—C13—C14	107.3 (2)	C22A—S1A—C21A	96.0 (7)
C16—C13—C14	109.0 (3)	S1A—C21A—H21D	109.5
C13—C14—H14A	109.5	S1A—C21A—H21E	109.5
C13—C14—H14B	109.5	H21D—C21A—H21E	109.5
H14A—C14—H14B	109.5	S1A—C21A—H21F	109.5
C13—C14—H14C	109.5	H21D—C21A—H21F	109.5
H14A—C14—H14C	109.5	H21E—C21A—H21F	109.5
H14B—C14—H14C	109.5	S1A—C22A—H22D	109.5
C13—C15—H15A	109.5	S1A—C22A—H22E	109.5
C13—C15—H15B	109.5	H22D—C22A—H22E	109.5
H15A—C15—H15B	109.5	S1A—C22A—H22F	109.5
C13—C15—H15C	109.5	H22D—C22A—H22F	109.5
H15A—C15—H15C	109.5	H22E—C22A—H22F	109.5
H15B—C15—H15C	109.5	H2A—O2—H2B	88 (6)
C13—C16—H16A	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1i	0.87 (1)	2.11 (2)	2.954 (7)	165 (7)
O2—H2A···S1Ai	0.87 (1)	2.71 (2)	3.565 (14)	167 (7)
O2—H2A···O1Ai	0.87 (1)	1.68 (4)	2.51 (3)	157 (8)
O2—H2B···O1ii	0.87 (1)	2.20 (2)	3.054 (9)	171 (7)
O2—H2B···S1Aii	0.87 (1)	1.84 (4)	2.604 (12)	146 (7)
O2—H2B···O1Aii	0.87 (1)	2.30 (4)	3.17 (4)	173 (7)
C14—H14B···Cl2iii	0.96	2.96	3.884 (1)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O1i	0.87 (1)	2.11 (2)	2.954 (7)	165 (7)
O2—H2A⋯S1A i	0.87 (1)	2.71 (2)	3.565 (14)	167 (7)
O2—H2A⋯O1A i	0.87 (1)	1.68 (4)	2.51 (3)	157 (8)
O2—H2B⋯O1ii	0.87 (1)	2.20 (2)	3.054 (9)	171 (7)
O2—H2B⋯S1A ii	0.87 (1)	1.84 (4)	2.604 (12)	146 (7)
O2—H2B⋯O1A ii	0.87 (1)	2.30 (4)	3.17 (4)	173 (7)
C14—H14B⋯Cl2iii	0.96	2.96	3.884 (1)	163

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