A trinuclear palladium(II) complex containing N,S-coordinating 2-(benzyl­sulfanyl)anilinide and 1,3-benzo­thia­zole-2-thiol­ate ligands with a central square-planar PdN₄ motif

The reaction of di­chlorido­(cod)palladium(II) (cod = 1,5-cyclo­octa­diene) with 2-(benzyl­sulfanyl)aniline followed by heating in N,N-di­methyl­formamide (DMF) produces the linear trinuclear Pd₃ complex bis­(μ₂-1,3-benzo­thia­zole-2-thiol­ato)bis[μ₂-2-(benzyl­sulfanyl)anilinido]di­chlorido­tri­palla­dium(II) N,N-di­methyl­formamide disolvate, [Pd₃(C₇H₄NS₂)₂(C₁₃H₁₂NS)₂Cl₂]·2C₃H₇NO. The mol­ecule has symmetry and a Pd...Pd separation of 3.2012 (4) Å. The outer Pd^II atoms have a square-planar geometry formed by an N,S-chelating 2-(benzyl­sulfanyl)anilinide ligand, a chloride ligand and the thiol­ate S atom of a bridging 1,3-benzo­thia­zole-2-thiol­ate ligand, while the central Pd^II core shows an all N-coordinated square-planar geometry. The geometry is perfectly planar within the PdN₄ core and the N—Pd—N bond angles differ significantly [84.72 (15)° for the N atoms of ligands coordinated to the same outer Pd atom and 95.28 (15)° for the N atoms of ligands coordinated to different outer Pd atoms]. This trinuclear Pd₃ complex is the first example of one in which 1,3-benzo­thia­zole-2-thiol­ate ligands are only N-coordinated to one Pd centre. The 1,3-benzo­thia­zole-2-thiol­ate ligands were formed in situ from 2-(benzyl­sulfanyl)aniline.

Computing details

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXD (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2013); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Bis(1,3-benzothiazole-2-thiolato)bis[µ₂-2-(benzylsulfanyl)anilinido]dichloridotripalladium(II) N,N-dimethylformamide disolvate

Crystal data

[Pd3(C7H4NS2)2(C13H12NS)2Cl2]·2C3H7NO	F(000) = 1296
Mr = 1297.35	Dx = 1.693 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.4298 (6) Å	Cell parameters from 5378 reflections
b = 10.6137 (5) Å	θ = 2.2–23.3°
c = 19.562 (1) Å	µ = 1.44 mm^−1
β = 99.5443 (7)°	T = 173 K
V = 2545.0 (2) Å^3	Rod, yellow
Z = 2	0.33 × 0.08 × 0.06 mm

Data collection

Bruker APEXII CCD area-detector diffractometer	4013 reflections with I > 2σ(I)
ω scans	Rint = 0.060
Absorption correction: integration SADABS (Bruker, 2008)	θmax = 26.4°, θmin = 1.8°
Tmin = 0.828, Tmax = 0.957	h = −15→15
19908 measured reflections	k = −13→13
5222 independent reflections	l = −24→24

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: mixed
wR(F^2) = 0.089	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0286P)^2 + 5.4894P] where P = (Fo^2 + 2Fc^2)/3
5222 reflections	(Δ/σ)max < 0.001
301 parameters	Δρmax = 1.55 e Å^−3
0 restraints	Δρmin = −0.55 e Å^−3

Special details

Experimental. Spectroscopic analysis for [2-(benzylsulfanyl)aniline]PdCl₂, (2): ¹H NMR (400 MHz, dmso-d₆): δ = 4.50 (s, 2H, CH₂-S), 5.50 (br, 2H, NH₂), 7.16 (d, J = 7.3 Hz, 1H, CH arom.), 7.22–7.40 (m, 7H, CH arom.), 7.51 (dd, J₁ = 8 Hz, J₂ = 1.2 Hz, 1H, CH arom.); ¹³C{¹H} NMR (100.6 MHz, dmso-d₆): δ = 45.5 (CH₂—S), 127.2, 127.3 (C-CH₂), 127.9, 128.5, 130.2, 131.1, 132.1, 133.5 (C-S), 147.1(C-NH₂). HRMS analysis: m/z 324.9764 (8%), 323.9736 (42), 322.9749 (15), 321.9718 (87), 320.9732 (19), 319.9712 (100), 318.9737 (75), 317.9684 (43), 316.9585 (10), 315.9609 (7); theoretical 323.9731 (40), 322.9731 (15), 321.9731 (90), 320.9731 (22), 319.9731 (100), 318.9731 (80), 317.9731 (38).

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 (Ų)

	x	y	z	Uiso*/Ueq
Pd1	0.0000	0.0000	0.5000	0.02409 (12)
Pd2	0.22120 (3)	−0.10788 (3)	0.45895 (2)	0.02543 (10)
Cl1	0.35824 (10)	−0.25800 (12)	0.48951 (7)	0.0405 (3)
S1	−0.10261 (11)	−0.31894 (13)	0.34993 (8)	0.0453 (3)
S2	0.09909 (10)	−0.27521 (11)	0.45263 (6)	0.0323 (3)
S3	0.34647 (10)	0.04961 (12)	0.47700 (6)	0.0333 (3)
N1	−0.0744 (3)	−0.1174 (3)	0.42414 (19)	0.0275 (8)
N2	0.1096 (3)	0.0305 (4)	0.4342 (2)	0.0271 (9)
H2N	0.079 (4)	0.006 (4)	0.400 (2)	0.022 (13)*
C1	−0.0247 (4)	−0.2249 (4)	0.4130 (2)	0.0322 (11)
C2	−0.2045 (4)	−0.2044 (5)	0.3368 (3)	0.0403 (12)
C3	−0.1734 (4)	−0.1020 (5)	0.3794 (2)	0.0312 (10)
C4	−0.2381 (4)	0.0072 (5)	0.3733 (3)	0.0410 (12)
H4	−0.2169	0.0792	0.4011	0.049*
C5	−0.3334 (4)	0.0069 (6)	0.3257 (3)	0.0492 (15)
H5	−0.3782	0.0799	0.3212	0.059*
C6	−0.3651 (5)	−0.0960 (7)	0.2849 (3)	0.0579 (17)
H6	−0.4319	−0.0934	0.2532	0.070*
C7	−0.3011 (5)	−0.2034 (6)	0.2891 (3)	0.0547 (16)
H7	−0.3225	−0.2743	0.2604	0.066*
C10	0.4334 (4)	0.0488 (5)	0.4103 (3)	0.0409 (12)
H10A	0.4899	0.1145	0.4222	0.049*
H10B	0.4715	−0.0334	0.4125	0.049*
C11	0.3800 (4)	0.0697 (5)	0.3374 (3)	0.0334 (11)
C12	0.3246 (4)	−0.0269 (5)	0.2991 (3)	0.0443 (13)
H12	0.3162	−0.1061	0.3202	0.053*
C13	0.2815 (5)	−0.0079 (6)	0.2301 (3)	0.0535 (16)
H13	0.2418	−0.0733	0.2041	0.064*
C14	0.2961 (5)	0.1061 (6)	0.1989 (3)	0.0525 (15)
H14	0.2669	0.1189	0.1514	0.063*
C15	0.3526 (4)	0.2006 (5)	0.2366 (3)	0.0454 (13)
H15	0.3633	0.2787	0.2150	0.054*
C16	0.3938 (4)	0.1831 (5)	0.3051 (3)	0.0395 (12)
H16	0.4324	0.2496	0.3309	0.047*
C21	0.2601 (4)	0.1813 (4)	0.4554 (2)	0.0299 (10)
C22	0.1505 (4)	0.1567 (4)	0.4352 (2)	0.0307 (11)
C23	0.0799 (4)	0.2585 (5)	0.4187 (3)	0.0394 (12)
H23	0.0043	0.2442	0.4031	0.047*
C24	0.1198 (5)	0.3803 (5)	0.4251 (3)	0.0476 (14)
H24	0.0711	0.4490	0.4141	0.057*
C25	0.2295 (5)	0.4037 (5)	0.4473 (3)	0.0473 (14)
H25	0.2556	0.4879	0.4527	0.057*
C26	0.3010 (4)	0.3033 (5)	0.4616 (3)	0.0401 (12)
H26	0.3770	0.3176	0.4754	0.048*
O1S	−0.0054 (3)	−0.0068 (4)	0.29370 (19)	0.0567 (11)
N1S	−0.0430 (5)	0.0268 (6)	0.1793 (2)	0.0665 (16)
C1S	0.0115 (5)	0.0477 (6)	0.2422 (3)	0.0528 (15)
H1S	0.0676	0.1095	0.2473	0.063*
C2S	−0.1323 (6)	−0.0610 (8)	0.1675 (4)	0.087 (3)
H2SA	−0.2012	−0.0147	0.1566	0.104*
H2SB	−0.1326	−0.1118	0.2093	0.104*
H2SC	−0.1239	−0.1162	0.1286	0.104*
C3S	−0.0199 (8)	0.0979 (11)	0.1201 (4)	0.137 (4)
H3SA	0.0316	0.1658	0.1362	0.165*
H3SB	−0.0877	0.1341	0.0952	0.165*
H3SC	0.0122	0.0419	0.0891	0.165*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pd1	0.0281 (3)	0.0218 (2)	0.0229 (2)	0.0046 (2)	0.0061 (2)	0.0013 (2)
Pd2	0.02734 (19)	0.02373 (18)	0.02492 (18)	0.00238 (15)	0.00345 (14)	−0.00043 (15)
Cl1	0.0342 (7)	0.0322 (7)	0.0519 (8)	0.0078 (5)	−0.0023 (6)	−0.0014 (6)
S1	0.0432 (8)	0.0375 (8)	0.0531 (8)	−0.0099 (6)	0.0016 (7)	−0.0138 (6)
S2	0.0337 (7)	0.0223 (6)	0.0412 (7)	0.0000 (5)	0.0070 (5)	−0.0021 (5)
S3	0.0326 (7)	0.0334 (6)	0.0311 (6)	−0.0033 (5)	−0.0023 (5)	0.0023 (5)
N1	0.027 (2)	0.029 (2)	0.0267 (19)	0.0011 (17)	0.0057 (16)	0.0035 (16)
N2	0.034 (2)	0.024 (2)	0.023 (2)	0.0024 (17)	0.0054 (18)	−0.0038 (17)
C1	0.052 (3)	0.018 (2)	0.030 (2)	0.000 (2)	0.018 (2)	−0.0025 (19)
C2	0.032 (3)	0.049 (3)	0.040 (3)	−0.007 (2)	0.004 (2)	0.001 (3)
C3	0.025 (2)	0.044 (3)	0.024 (2)	0.002 (2)	0.0046 (19)	0.002 (2)
C4	0.034 (3)	0.057 (3)	0.034 (3)	0.011 (3)	0.012 (2)	0.006 (3)
C5	0.031 (3)	0.079 (4)	0.038 (3)	0.014 (3)	0.006 (2)	0.009 (3)
C6	0.029 (3)	0.096 (5)	0.045 (3)	−0.003 (3)	−0.004 (3)	0.011 (4)
C7	0.044 (4)	0.074 (4)	0.042 (3)	−0.015 (3)	−0.004 (3)	−0.005 (3)
C10	0.027 (3)	0.042 (3)	0.052 (3)	0.000 (2)	0.003 (2)	0.005 (3)
C11	0.023 (2)	0.038 (3)	0.040 (3)	0.001 (2)	0.009 (2)	−0.002 (2)
C12	0.052 (3)	0.040 (3)	0.044 (3)	−0.008 (3)	0.017 (3)	0.005 (2)
C13	0.066 (4)	0.058 (4)	0.038 (3)	−0.027 (3)	0.013 (3)	−0.008 (3)
C14	0.059 (4)	0.066 (4)	0.034 (3)	−0.003 (3)	0.011 (3)	0.006 (3)
C15	0.055 (4)	0.039 (3)	0.045 (3)	0.007 (3)	0.015 (3)	0.007 (3)
C16	0.038 (3)	0.033 (3)	0.048 (3)	−0.003 (2)	0.010 (2)	0.000 (2)
C21	0.042 (3)	0.024 (2)	0.024 (2)	−0.002 (2)	0.005 (2)	0.0016 (18)
C22	0.043 (3)	0.025 (2)	0.026 (2)	0.006 (2)	0.013 (2)	0.0015 (19)
C23	0.045 (3)	0.032 (3)	0.042 (3)	0.009 (2)	0.010 (2)	0.005 (2)
C24	0.063 (4)	0.025 (3)	0.057 (4)	0.006 (3)	0.019 (3)	0.006 (2)
C25	0.073 (4)	0.024 (3)	0.046 (3)	−0.009 (3)	0.014 (3)	0.002 (2)
C26	0.045 (3)	0.038 (3)	0.035 (3)	−0.009 (2)	0.003 (2)	0.001 (2)
O1S	0.062 (3)	0.077 (3)	0.031 (2)	−0.007 (2)	0.0068 (19)	0.007 (2)
N1S	0.067 (4)	0.100 (5)	0.033 (3)	0.021 (3)	0.009 (3)	0.016 (3)
C1S	0.042 (3)	0.064 (4)	0.053 (4)	0.004 (3)	0.010 (3)	0.008 (3)
C2S	0.068 (5)	0.134 (7)	0.055 (4)	0.013 (5)	−0.001 (4)	−0.029 (5)
C3S	0.140 (9)	0.220 (12)	0.059 (5)	0.033 (8)	0.038 (6)	0.066 (7)

Geometric parameters (Å, º)

Pd1—N1	2.039 (4)	C11—C12	1.385 (7)
Pd1—N1^i	2.039 (4)	C12—C13	1.380 (8)
Pd1—N2^i	2.050 (4)	C12—H12	0.9500
Pd1—N2	2.050 (4)	C13—C14	1.381 (8)
Pd1—Pd2^i	3.2012 (4)	C13—H13	0.9500
Pd2—N2	2.023 (4)	C14—C15	1.367 (8)
Pd2—S3	2.2718 (13)	C14—H14	0.9500
Pd2—S2	2.3261 (12)	C15—C16	1.366 (7)
Pd2—Cl1	2.3366 (12)	C15—H15	0.9500
S1—C2	1.743 (6)	C16—H16	0.9500
S1—C1	1.749 (5)	C21—C22	1.379 (7)
S2—C1	1.690 (5)	C21—C26	1.389 (6)
S3—C21	1.770 (5)	C22—C23	1.396 (6)
S3—C10	1.828 (5)	C23—C24	1.383 (7)
N1—C1	1.333 (6)	C23—H23	0.9500
N1—C3	1.396 (6)	C24—C25	1.383 (8)
N2—C22	1.431 (6)	C24—H24	0.9500
N2—H2N	0.76 (5)	C25—C26	1.387 (7)
C2—C3	1.386 (7)	C25—H25	0.9500
C2—C7	1.394 (7)	C26—H26	0.9500
C3—C4	1.405 (7)	O1S—C1S	1.210 (7)
C4—C5	1.379 (7)	N1S—C1S	1.322 (8)
C4—H4	0.9500	N1S—C2S	1.438 (9)
C5—C6	1.372 (9)	N1S—C3S	1.449 (9)
C5—H5	0.9500	C1S—H1S	0.9500
C6—C7	1.385 (9)	C2S—H2SA	0.9800
C6—H6	0.9500	C2S—H2SB	0.9800
C7—H7	0.9500	C2S—H2SC	0.9800
C10—C11	1.486 (7)	C3S—H3SA	0.9800
C10—H10A	0.9900	C3S—H3SB	0.9800
C10—H10B	0.9900	C3S—H3SC	0.9800
C11—C16	1.383 (7)
N1—Pd1—N1^i	180.00 (19)	H10A—C10—H10B	107.2
N1—Pd1—N2^i	95.28 (15)	C16—C11—C12	119.0 (5)
N1^i—Pd1—N2^i	84.72 (15)	C16—C11—C10	119.9 (5)
N1—Pd1—N2	84.72 (15)	C12—C11—C10	120.8 (5)
N1^i—Pd1—N2	95.28 (15)	C13—C12—C11	119.9 (5)
N2^i—Pd1—N2	180.0	C13—C12—H12	120.1
N1—Pd1—Pd2^i	95.54 (10)	C11—C12—H12	120.1
N1^i—Pd1—Pd2^i	84.46 (10)	C12—C13—C14	120.1 (5)
N2^i—Pd1—Pd2^i	37.90 (11)	C12—C13—H13	119.9
N2—Pd1—Pd2^i	142.10 (11)	C14—C13—H13	119.9
N2—Pd2—S3	85.87 (12)	C15—C14—C13	119.8 (5)
N2—Pd2—S2	97.26 (12)	C15—C14—H14	120.1
S3—Pd2—S2	173.94 (5)	C13—C14—H14	120.1
N2—Pd2—Cl1	176.43 (12)	C16—C15—C14	120.3 (5)
S3—Pd2—Cl1	90.59 (5)	C16—C15—H15	119.9
S2—Pd2—Cl1	86.25 (4)	C14—C15—H15	119.9
C2—S1—C1	90.6 (2)	C15—C16—C11	120.8 (5)
C1—S2—Pd2	108.63 (16)	C15—C16—H16	119.6
C21—S3—C10	103.9 (2)	C11—C16—H16	119.6
C21—S3—Pd2	99.83 (16)	C22—C21—C26	122.1 (5)
C10—S3—Pd2	110.90 (18)	C22—C21—S3	116.8 (3)
C1—N1—C3	112.5 (4)	C26—C21—S3	121.1 (4)
C1—N1—Pd1	118.4 (3)	C21—C22—C23	118.3 (5)
C3—N1—Pd1	129.1 (3)	C21—C22—N2	120.8 (4)
C22—N2—Pd2	116.6 (3)	C23—C22—N2	120.9 (4)
C22—N2—Pd1	114.2 (3)	C24—C23—C22	120.0 (5)
Pd2—N2—Pd1	103.61 (17)	C24—C23—H23	120.0
C22—N2—H2N	117 (4)	C22—C23—H23	120.0
Pd2—N2—H2N	101 (4)	C23—C24—C25	121.1 (5)
Pd1—N2—H2N	102 (4)	C23—C24—H24	119.4
N1—C1—S2	127.3 (4)	C25—C24—H24	119.4
N1—C1—S1	112.7 (4)	C24—C25—C26	119.4 (5)
S2—C1—S1	119.9 (3)	C24—C25—H25	120.3
C3—C2—C7	121.4 (5)	C26—C25—H25	120.3
C3—C2—S1	109.6 (4)	C25—C26—C21	119.1 (5)
C7—C2—S1	128.9 (5)	C25—C26—H26	120.5
C2—C3—N1	114.5 (4)	C21—C26—H26	120.5
C2—C3—C4	119.8 (5)	C1S—N1S—C2S	121.4 (6)
N1—C3—C4	125.7 (5)	C1S—N1S—C3S	121.1 (7)
C5—C4—C3	118.2 (5)	C2S—N1S—C3S	117.4 (7)
C5—C4—H4	120.9	O1S—C1S—N1S	124.2 (6)
C3—C4—H4	120.9	O1S—C1S—H1S	117.9
C6—C5—C4	121.7 (6)	N1S—C1S—H1S	117.9
C6—C5—H5	119.1	N1S—C2S—H2SA	109.5
C4—C5—H5	119.1	N1S—C2S—H2SB	109.5
C5—C6—C7	120.9 (5)	H2SA—C2S—H2SB	109.5
C5—C6—H6	119.5	N1S—C2S—H2SC	109.5
C7—C6—H6	119.5	H2SA—C2S—H2SC	109.5
C6—C7—C2	117.9 (6)	H2SB—C2S—H2SC	109.5
C6—C7—H7	121.0	N1S—C3S—H3SA	109.5
C2—C7—H7	121.0	N1S—C3S—H3SB	109.5
C11—C10—S3	117.5 (3)	H3SA—C3S—H3SB	109.5
C11—C10—H10A	107.9	N1S—C3S—H3SC	109.5
S3—C10—H10A	107.9	H3SA—C3S—H3SC	109.5
C11—C10—H10B	107.9	H3SB—C3S—H3SC	109.5
S3—C10—H10B	107.9
N2—Pd2—S2—C1	13.2 (2)	C2—C3—C4—C5	2.0 (7)
Cl1—Pd2—S2—C1	−167.44 (17)	N1—C3—C4—C5	179.2 (4)
N2—Pd2—S3—C21	−1.04 (18)	C3—C4—C5—C6	−0.4 (8)
Cl1—Pd2—S3—C21	179.32 (15)	C4—C5—C6—C7	−1.1 (9)
N2—Pd2—S3—C10	−110.2 (2)	C5—C6—C7—C2	0.9 (9)
Cl1—Pd2—S3—C10	70.19 (18)	C3—C2—C7—C6	0.8 (8)
N2^i—Pd1—N1—C1	−109.9 (3)	S1—C2—C7—C6	−174.7 (4)
N2—Pd1—N1—C1	70.1 (3)	C21—S3—C10—C11	−44.4 (5)
Pd2^i—Pd1—N1—C1	−148.0 (3)	Pd2—S3—C10—C11	62.0 (4)
N2^i—Pd1—N1—C3	70.7 (4)	S3—C10—C11—C16	107.0 (5)
N2—Pd1—N1—C3	−109.3 (4)	S3—C10—C11—C12	−79.0 (6)
Pd2^i—Pd1—N1—C3	32.7 (4)	C16—C11—C12—C13	−1.8 (8)
S3—Pd2—N2—C22	2.2 (3)	C10—C11—C12—C13	−175.8 (5)
S2—Pd2—N2—C22	177.0 (3)	C11—C12—C13—C14	1.7 (9)
S3—Pd2—N2—Pd1	−124.25 (16)	C12—C13—C14—C15	−0.5 (9)
S2—Pd2—N2—Pd1	50.53 (16)	C13—C14—C15—C16	−0.6 (9)
N1—Pd1—N2—C22	144.3 (3)	C14—C15—C16—C11	0.5 (8)
N1^i—Pd1—N2—C22	−35.7 (3)	C12—C11—C16—C15	0.7 (7)
Pd2^i—Pd1—N2—C22	52.0 (4)	C10—C11—C16—C15	174.8 (5)
N1—Pd1—N2—Pd2	−87.76 (18)	C10—S3—C21—C22	114.5 (4)
N1^i—Pd1—N2—Pd2	92.24 (18)	Pd2—S3—C21—C22	−0.1 (4)
Pd2^i—Pd1—N2—Pd2	180.000 (1)	C10—S3—C21—C26	−68.2 (4)
C3—N1—C1—S2	176.4 (3)	Pd2—S3—C21—C26	177.3 (4)
Pd1—N1—C1—S2	−3.0 (5)	C26—C21—C22—C23	1.8 (7)
C3—N1—C1—S1	−4.1 (5)	S3—C21—C22—C23	179.2 (3)
Pd1—N1—C1—S1	176.44 (19)	C26—C21—C22—N2	−175.4 (4)
Pd2—S2—C1—N1	−44.2 (4)	S3—C21—C22—N2	2.0 (6)
Pd2—S2—C1—S1	136.3 (2)	Pd2—N2—C22—C21	−3.0 (5)
C2—S1—C1—N1	1.8 (4)	Pd1—N2—C22—C21	118.0 (4)
C2—S1—C1—S2	−178.7 (3)	Pd2—N2—C22—C23	179.8 (3)
C1—S1—C2—C3	1.0 (4)	Pd1—N2—C22—C23	−59.2 (5)
C1—S1—C2—C7	176.9 (5)	C21—C22—C23—C24	−2.2 (7)
C7—C2—C3—N1	−179.8 (5)	N2—C22—C23—C24	175.0 (4)
S1—C2—C3—N1	−3.5 (5)	C22—C23—C24—C25	0.4 (8)
C7—C2—C3—C4	−2.2 (7)	C23—C24—C25—C26	1.7 (8)
S1—C2—C3—C4	174.1 (4)	C24—C25—C26—C21	−2.1 (8)
C1—N1—C3—C2	5.0 (6)	C22—C21—C26—C25	0.3 (7)
Pd1—N1—C3—C2	−175.6 (3)	S3—C21—C26—C25	−176.9 (4)
C1—N1—C3—C4	−172.4 (4)	C2S—N1S—C1S—O1S	2.8 (10)
Pd1—N1—C3—C4	7.0 (7)	C3S—N1S—C1S—O1S	178.6 (7)

Symmetry code: (i) −x, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1S	0.76 (5)	2.17 (5)	2.907 (6)	163 (5)