Di­chlorido­(4,4′-di-tert-butyl-2,2′-bi­pyridine-κ2N,N′)palladium(II) dimethyl sulfoxide monosolvate monohydrate

Gutiérrez-Márquez, R.A.; Crisóstomo-Lucas, C.; Reyes-Martínez, R.; Hernández-Ortega, S.; Morales-Morales, D.

doi:10.1107/S1600536814009453

metal-organic compounds

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ISSN: 2056-9890

Volume 70| Part 6| June 2014| Pages m200-m201

doi:10.1107/S1600536814009453

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Dichlorido(4,4′-di-tert-butyl-2,2′-bipyridine-κ²N,N′)palladium(II) dimethyl sulfoxide monosolvate monohydrate

Ricardo A. Gutiérrez-Márquez,^a Carmela Crisóstomo-Lucas,^a Reyna Reyes-Martínez,^a ^* Simón Hernández-Ortega ^a and David Morales-Morales ^a

^aInstituto de Química, Universidad Nacional Autónoma de México, Circuito exterior, Ciudad Universitaria, México, DF, 04510, Mexico
^*Correspondence e-mail: rrm@uaem.mx

(Received 13 April 2014; accepted 26 April 2014; online 10 May 2014)

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 molecules form linear chains along [100] by O—H⋯O and O—H⋯S hydrogen bonds, generating eight- and 12-membered rings. C—H⋯Cl interactions link the chains, forming a three-dimensional arrangement. In addition, the 4,4-di-tert-butyl-2,2′-bipyridine ligand exhibits π–π stacking interactions [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_r = 541.83
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.028
wR(F²) = 0.076
S = 1.01
4343 reflections
302 parameters
118 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.55 e Å⁻³

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⋯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
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x, y+1, z; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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 ).

Supporting information

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

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

checkCIF report

Introduction top

The N—N chelate ligands have been studied with a variety of transition metals as building blocks in supramolecular chemistry. 2,2'-Bipyridine and its derivatives have been employed as auxiliary ligands in transition metal complexes usually serving as blocking ligands. Thus, given our continuous interest in the synthesis of metal complexes with potential catalytic activities in cross coupling reactions and the use of N—N quelate ligands (Corona-Rodríguez et al., 2007; Basauri-Molina et al., 2010), we report here the crystal structure of the compound [PdCl₂(^tBubpy)]·(CH₃)₂SO)·H₂O (^tBubpy = 4,4'-di-tert-butyl-2,2'-bipyridine) as a solvated compound. The crystal structure of the non-solvated complex has been reported previously (Qin et al., 2002; MacLean et al., 2002), and this compound has served as precursor in the formation of metallomacrocycles (Qin et al., 2002; Tzeng et al., 2001) and due to its structure may present π interactions like π-π stacking and C—H···π interactions.

Experimental top

Synthesis and crystallization top

To a solution of [Pd(MeCN)₂Cl₂] (0.13 g, 0.501 mmol) in ethanol (10 ml), 4,4'-di-tert-butyl-2,2'-bipyridine (0.1 g, 0.651 mmol) was added under stirring. The resulting orange solution was allowed to react for 4 h under stirring at room temperature. After this time the solution was filtered and the solvent taken off under vacuum to produce a yellow solid. Crystals suitable for X-ray diffraction experiments were obtained from dimethylsulfoxide as solvent at room temperature.

¹H-NMR (300 MHz, DMSO–D₆): d 1.42 (s, 18H, ^tBu), 7.82 (d, 2H, CH), 8.60 (s, 2H, CH), 9.02 (d, 2H, CH). ¹³C-NMR (75.6 MHz, DMSO-D₆): d 30.3 (s, CH₃), 39.9 (s, C(CH₃)₃), 121.7 (s, CH), 124.4 (s, CH), 149.9 (s, CH), 156.4 (s, C), 165.7 (s, C).

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1.

H atoms were included in calculated positions (C—H = 0.93 Å for aromatic H, C—H = 0.96 Å for methyl H), and refined using a riding model with U iso (H) = 1.2Ueq of the carrier atom. H atoms on O were located on the Fourier map and refined isotropically.

The DMSO solvent is disordered and was refined in two major positions using a free variable of Site Occupational Factor (SOF), the ratio of disordered atoms was 87/13 of SOF.

In the refinement six reflections, (0 0 1), (0 5 1), (1 2 2), (1 2 0), (-1 2 4) and (-2 0 2), were considered as disagreeable and were omitted.

Results and discussion top

The title compound is formed by a molecule of the complex [PdCl₂(^tBubpy)], one molecule of dimethylsulfoxide (disordered) and one molecule of water, the structure is presented in Figure 1.

The coordination around the Pd(II) ion adopts a distorted square planar geometry, surrounded by two chloride atoms and one 4,4'-di-tert-butyl-2,2'-bipyridine ligand coordinated in a chelate fashion with a bite angle of 80.07 (8)°. The Pd—Cl bond distances are 2.2880 (9) and 2.2832 (9) Å which are similar to those found in the non-solvated structure (Qin et al., 2002; MacLean et al., 2002). The Pd—N bond distances are 2.022 (2) and 2.027 (2) Å which are close in value to those found for the compound [PdCl₂(^tBubpy)] and slightly smaller than those observed in the diiodo complex [PdI₂(^tBubpy)] (2.047 (4), 2.062 (4) Å) (Jones et al., 2007).

Both the dimethylsulfoxide and water molecules interact via hydrogen bonds (O—H···O, C—H···O) forming 8- and 12-member rings that generate a linear chain in the [100] direction (Table 1). The 4,4'-di-tert-butyl-2,2'-bipyridine ligand presents π-π stacking interactions which extend along the a axis [100] generated by the symmetry operations 1-x, 1-y, 1-z and -x, 1-y, 1-z. The two centroid-centroid distances between the ligand rings are 3.8741 (15) and 3.8353 (15) Å respectively. The crystal arrangement is complemented by C—H···Cl interactions which link the linear arrangement of π-π stacking in layers parallel to (100).

Related literature top

For compounds with N—N ligands, see: Corona-Rodríguez et al. (2007); Basauri-Molina et al. (2010). For 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 compound and their crystal structure, see: Jones et al. (2007).

Computing details top

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); 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 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The asymmetric unit of the title compound. All non-hydrogen atoms are shown as ellipsoids with probability level of 50%.
	Fig. 2. Packing of the molecular entities in the structure of the title compound. Hydrogen bonds interaction as shown by dashed lines.

Dichlorido(4,4'-di-tert-butyl-2,2'-bipyridine-κ²N,N')palladium(II) dimethyl sulfoxide monosolvate monohydrate top

Crystal data top

[PdCl₂(C₁₈H₂₄N₂)]·C₂H₆OS·H₂O	F(000) = 1112
M_r = 541.83	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.042P)² + 0.5P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.002
4343 reflections	Δρ_max = 0.39 e Å⁻³
302 parameters	Δρ_min = −0.55 e Å⁻³

Crystal data top

[PdCl₂(C₁₈H₂₄N₂)]·C₂H₆OS·H₂O	V = 2399.03 (17) Å³
M_r = 541.83	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.4869 (3) Å	µ = 1.10 mm⁻¹
b = 19.5052 (8) Å	T = 298 K
c = 16.8538 (7) Å	0.42 × 0.19 × 0.09 mm
β = 102.907 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	4343 independent reflections
Absorption correction: analytical (SADABS; Sheldrick, 2008)	3766 reflections with I > 2σ(I)
T_min = 0.780, T_max = 0.932	R_int = 0.030
13351 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	118 restraints
wR(F²) = 0.076	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.39 e Å⁻³
4343 reflections	Δρ_min = −0.55 e Å⁻³
302 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y+1, z; (iii) −x+1, y−1/2, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1ⁱ	0.869 (10)	2.11 (2)	2.954 (7)	165 (7)
O2—H2A···S1Aⁱ	0.869 (10)	2.71 (2)	3.565 (14)	167 (7)
O2—H2A···O1Aⁱ	0.869 (10)	1.68 (4)	2.51 (3)	157 (8)
O2—H2B···O1ⁱⁱ	0.867 (10)	2.195 (17)	3.054 (9)	171 (7)
O2—H2B···S1Aⁱⁱ	0.867 (10)	1.84 (4)	2.604 (12)	146 (7)
O2—H2B···O1Aⁱⁱ	0.867 (10)	2.30 (4)	3.17 (4)	173 (7)
C14—H14B···Cl2ⁱⁱⁱ	0.960	2.96	3.884 (1)	163

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y+1, z; (iii) −x+1, y−1/2, −z+3/2.

Acknowledgements

Financial support of this research by CONACyT (grant CB2010–154732) and PAPIIT (grants IN201711–3 and IN213214–3) is gratefully acknowledged.

References

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Volume 70| Part 6| June 2014| Pages m200-m201

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