(2,2'-Bipyridine-κ(2) N,N')[bis-(diphenyl-thio-phosphino-yl)meth-yl]lithium(I) benzene monosolvate.

In the title benzene-solvated heteroleptic lithium complex, [Li(C25H21P2S2)(C10H8N2)]·C6H6, the Li(I) ion is four-coordinated in a distorted tetra-hedral geometry by two S atoms and two N atoms of the two chelating ligands, viz. bis-(diphenyl-thio-phosphino-yl)methyl and 2,2'-bipyridine. The 2,2'-bipyridine mol-ecule is slightly twisted with a dihedral angle between the pyridine rings of 7.35 (12)°. Intra-molecular C-H⋯S hydrogen bonds are present. In the crystal, mol-ecules are stacked along the c axis by π-π inter-actions, with centroid-centroid distances of 3.6021 (15) and 3.6401 (16) Å. The crystal structure also features weak C-H⋯π inter-actions.

Related literature

For standard bond lengths, see: Allen et al. (1987 ▶). For background to and applications of thio­phosphinoyl ligands and their complexes, see: Amir et al. (2013 ▶); Leung, Wan & Mak (2010 ▶); Leung, Wan, Kan & Mak (2010 ▶); Ren et al. (2011 ▶). For related structures, see: Thirumoorthi & Chivers (2012 ▶).

Experimental

Crystal data

[Li(C25H21P2S2)(C10H8N2)]·C6H6

M = 688.73

Triclinic,

a = 10.7654 (11) Å

b = 13.1295 (12) Å

c = 13.5498 (11) Å

α = 90.746 (2)°

β = 101.902 (1)°

γ = 109.257 (2)°

V = 1762.3 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.28 mm−1

T = 297 K

0.44 × 0.28 × 0.20 mm

Data collection

Bruker APEXII CCD area detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.889, T max = 0.947

10290 measured reflections

7517 independent reflections

5856 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.115

S = 1.04

7517 reflections

433 parameters

H-atom parameters constrained

Δρmax = 0.53 e Å−3

Δρmin = −0.39 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PLATON (Spek, 2009 ▶), Mercury (Macrae et al., 2006 ▶) and publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681300456X/rz5044sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681300456X/rz5044Isup2.hkl

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

[Li(C25H21P2S2)(C10H8N2)]·C6H6	Z = 2
Mr = 688.73	F(000) = 720
Triclinic, P1	Dx = 1.298 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.7654 (11) Å	Cell parameters from 7517 reflections
b = 13.1295 (12) Å	θ = 2.2–27.0°
c = 13.5498 (11) Å	µ = 0.28 mm−1
α = 90.746 (2)°	T = 297 K
β = 101.902 (1)°	Block, yellow
γ = 109.257 (2)°	0.44 × 0.28 × 0.20 mm
V = 1762.3 (3) Å3

Bruker APEXII CCD area detector diffractometer	7517 independent reflections
Radiation source: sealed tube	5856 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
φ and ω scans	θmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→13
Tmin = 0.889, Tmax = 0.947	k = −16→16
10290 measured reflections	l = −17→9

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.035P)2 + 0.9744P] where P = (Fo2 + 2Fc2)/3
7517 reflections	(Δ/σ)max = 0.001
433 parameters	Δρmax = 0.53 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C1	−0.1068 (3)	0.6986 (2)	0.4548 (2)	0.0263 (6)
H1	−0.1062	0.6450	0.4073	0.032*
C2	−0.2238 (3)	0.6835 (2)	0.4891 (2)	0.0313 (7)
H2	−0.3002	0.6196	0.4681	0.038*
C3	−0.2262 (3)	0.7641 (2)	0.5547 (2)	0.0275 (6)
H3	−0.3057	0.7571	0.5781	0.033*
C4	−0.1129 (2)	0.8542 (2)	0.58578 (18)	0.0203 (5)
H4	−0.1133	0.9105	0.6303	0.024*
C5	0.0030 (2)	0.86183 (19)	0.55080 (18)	0.0169 (5)
C6	0.1316 (2)	0.95504 (19)	0.58236 (17)	0.0157 (5)
C7	0.1516 (3)	1.0354 (2)	0.65794 (18)	0.0200 (5)
H7	0.0814	1.0335	0.6912	0.024*
C8	0.2748 (3)	1.1181 (2)	0.6840 (2)	0.0253 (6)
H8	0.2906	1.1731	0.7359	0.030*
C9	0.3747 (3)	1.1200 (2)	0.63387 (19)	0.0222 (6)
H9	0.4600	1.1763	0.6499	0.027*
C10	0.3469 (2)	1.0375 (2)	0.55958 (19)	0.0199 (5)
H10	0.4157	1.0388	0.5251	0.024*
C11	0.3737 (2)	0.95373 (18)	0.19821 (17)	0.0147 (5)
C12	0.4031 (2)	1.03724 (19)	0.27311 (18)	0.0178 (5)
H12	0.3388	1.0362	0.3121	0.021*
C13	0.5256 (3)	1.1220 (2)	0.2912 (2)	0.0230 (6)
H13	0.5453	1.1781	0.3429	0.028*
C14	0.6193 (3)	1.1248 (2)	0.2338 (2)	0.0236 (6)
H14	0.7034	1.1824	0.2467	0.028*
C15	0.5903 (2)	1.0436 (2)	0.1577 (2)	0.0220 (5)
H15	0.6538	1.0461	0.1176	0.026*
C16	0.4683 (2)	0.95842 (19)	0.14008 (18)	0.0184 (5)
H16	0.4489	0.9027	0.0879	0.022*
C17	0.1507 (2)	0.82567 (18)	0.04508 (17)	0.0139 (5)
C18	0.1161 (2)	0.91241 (19)	0.00406 (18)	0.0172 (5)
H18	0.1333	0.9761	0.0463	0.021*
C19	0.0566 (2)	0.9061 (2)	−0.09820 (19)	0.0220 (6)
H19	0.0337	0.9653	−0.1259	0.026*
C20	0.0309 (3)	0.8129 (2)	−0.15950 (19)	0.0230 (6)
H20	−0.0115	0.8079	−0.2291	0.028*
C21	0.0664 (3)	0.7273 (2)	−0.12038 (19)	0.0227 (6)
H21	0.0506	0.6643	−0.1632	0.027*
C22	0.1252 (2)	0.73354 (19)	−0.01822 (18)	0.0181 (5)
H22	0.1484	0.6741	0.0088	0.022*
C23	0.2662 (2)	0.72073 (18)	0.20470 (17)	0.0148 (5)
H23	0.3089	0.6989	0.1577	0.018*
C24	0.3158 (2)	0.53993 (18)	0.28467 (17)	0.0140 (5)
C25	0.4196 (2)	0.52524 (19)	0.35627 (18)	0.0181 (5)
H25	0.4558	0.5710	0.4176	0.022*
C26	0.4708 (2)	0.4439 (2)	0.33868 (19)	0.0215 (5)
H26	0.5420	0.4343	0.3879	0.026*
C27	0.4178 (2)	0.37688 (19)	0.2493 (2)	0.0210 (5)
H27	0.4523	0.3210	0.2375	0.025*
C28	0.3151 (3)	0.3913 (2)	0.1775 (2)	0.0233 (6)
H28	0.2790	0.3455	0.1162	0.028*
C29	0.2647 (2)	0.4725 (2)	0.19484 (19)	0.0207 (5)
H29	0.1944	0.4823	0.1450	0.025*
C30	0.0649 (2)	0.56099 (18)	0.29200 (18)	0.0141 (5)
C31	0.0284 (2)	0.49183 (19)	0.36662 (19)	0.0192 (5)
H31	0.0952	0.4905	0.4241	0.023*
C32	−0.1039 (3)	0.4254 (2)	0.3578 (2)	0.0244 (6)
H32	−0.1274	0.3784	0.4088	0.029*
C33	−0.2026 (3)	0.4275 (2)	0.2745 (2)	0.0269 (6)
H33	−0.2937	0.3827	0.2688	0.032*
C34	−0.1679 (3)	0.4950 (2)	0.1997 (2)	0.0280 (6)
H34	−0.2355	0.4963	0.1427	0.034*
C35	−0.0341 (2)	0.5614 (2)	0.2075 (2)	0.0211 (5)
H35	−0.0106	0.6067	0.1553	0.025*
C36	0.4914 (3)	0.7279 (2)	−0.0237 (2)	0.0252 (6)
H36	0.4141	0.7342	−0.0681	0.030*
C37	0.6179 (3)	0.8037 (2)	−0.0203 (2)	0.0257 (6)
H37	0.6273	0.8625	−0.0616	0.031*
C38	0.7308 (3)	0.7930 (2)	0.0440 (2)	0.0261 (6)
H38	0.8180	0.8440	0.0461	0.031*
C39	0.7159 (3)	0.7079 (2)	0.1048 (2)	0.0257 (6)
H39	0.7932	0.7008	0.1486	0.031*
C40	0.5902 (3)	0.6332 (2)	0.1025 (2)	0.0273 (6)
H40	0.5805	0.5754	0.1449	0.033*
C41	0.4776 (3)	0.6435 (2)	0.0373 (2)	0.0271 (6)
H41	0.3907	0.5920	0.0348	0.032*
Li1	0.1760 (4)	0.8253 (3)	0.4313 (3)	0.0221 (9)
N1	0.0051 (2)	0.78456 (16)	0.48517 (16)	0.0190 (4)
N2	0.22935 (19)	0.95594 (16)	0.53321 (15)	0.0156 (4)
P1	0.22202 (6)	0.83361 (5)	0.18020 (4)	0.01272 (14)
P2	0.24198 (6)	0.64311 (5)	0.30422 (4)	0.01215 (14)
S1	0.09223 (6)	0.85611 (5)	0.25669 (5)	0.01720 (14)
S2	0.31422 (6)	0.71102 (5)	0.44789 (4)	0.01617 (14)

	U11	U22	U33	U12	U13	U23
C1	0.0240 (14)	0.0195 (13)	0.0336 (16)	0.0075 (11)	0.0027 (12)	−0.0003 (11)
C2	0.0170 (13)	0.0250 (15)	0.0457 (18)	0.0021 (12)	0.0012 (12)	0.0063 (13)
C3	0.0168 (13)	0.0353 (16)	0.0339 (16)	0.0103 (12)	0.0102 (12)	0.0147 (13)
C4	0.0200 (13)	0.0285 (14)	0.0175 (13)	0.0137 (11)	0.0064 (10)	0.0080 (10)
C5	0.0190 (12)	0.0187 (12)	0.0165 (12)	0.0111 (10)	0.0034 (10)	0.0072 (10)
C6	0.0173 (12)	0.0209 (12)	0.0128 (12)	0.0106 (10)	0.0048 (9)	0.0060 (9)
C7	0.0239 (13)	0.0239 (13)	0.0166 (13)	0.0123 (11)	0.0072 (10)	0.0021 (10)
C8	0.0338 (15)	0.0230 (14)	0.0183 (13)	0.0112 (12)	0.0015 (11)	−0.0040 (10)
C9	0.0193 (13)	0.0205 (13)	0.0235 (14)	0.0046 (11)	0.0012 (10)	0.0030 (10)
C10	0.0187 (12)	0.0236 (13)	0.0210 (13)	0.0107 (11)	0.0066 (10)	0.0064 (10)
C11	0.0162 (12)	0.0152 (12)	0.0125 (11)	0.0070 (10)	0.0002 (9)	0.0018 (9)
C12	0.0220 (13)	0.0153 (12)	0.0158 (12)	0.0076 (10)	0.0016 (10)	0.0018 (9)
C13	0.0268 (14)	0.0152 (12)	0.0224 (14)	0.0067 (11)	−0.0039 (11)	−0.0011 (10)
C14	0.0163 (12)	0.0172 (13)	0.0295 (15)	0.0007 (10)	−0.0038 (11)	0.0062 (11)
C15	0.0182 (12)	0.0229 (13)	0.0256 (14)	0.0072 (11)	0.0056 (11)	0.0089 (11)
C16	0.0202 (12)	0.0163 (12)	0.0199 (13)	0.0077 (10)	0.0047 (10)	0.0027 (10)
C17	0.0108 (11)	0.0168 (12)	0.0129 (11)	0.0025 (9)	0.0037 (9)	0.0025 (9)
C18	0.0195 (12)	0.0168 (12)	0.0166 (12)	0.0074 (10)	0.0051 (10)	0.0015 (9)
C19	0.0211 (13)	0.0279 (14)	0.0214 (13)	0.0124 (11)	0.0066 (11)	0.0098 (11)
C20	0.0224 (13)	0.0300 (14)	0.0137 (12)	0.0071 (12)	0.0007 (10)	0.0018 (10)
C21	0.0245 (13)	0.0238 (13)	0.0177 (13)	0.0055 (11)	0.0045 (11)	−0.0032 (10)
C22	0.0215 (13)	0.0175 (12)	0.0168 (12)	0.0078 (10)	0.0053 (10)	0.0040 (10)
C23	0.0183 (12)	0.0137 (11)	0.0151 (12)	0.0074 (10)	0.0064 (9)	0.0009 (9)
C24	0.0135 (11)	0.0137 (11)	0.0155 (12)	0.0040 (9)	0.0060 (9)	0.0033 (9)
C25	0.0163 (12)	0.0197 (12)	0.0165 (12)	0.0048 (10)	0.0016 (10)	−0.0005 (10)
C26	0.0196 (13)	0.0251 (14)	0.0239 (14)	0.0131 (11)	0.0042 (10)	0.0051 (11)
C27	0.0220 (13)	0.0150 (12)	0.0316 (15)	0.0103 (11)	0.0110 (11)	0.0052 (10)
C28	0.0247 (14)	0.0194 (13)	0.0250 (14)	0.0084 (11)	0.0026 (11)	−0.0047 (10)
C29	0.0192 (12)	0.0226 (13)	0.0217 (13)	0.0105 (11)	0.0021 (10)	0.0000 (10)
C30	0.0129 (11)	0.0124 (11)	0.0194 (12)	0.0060 (9)	0.0061 (9)	−0.0008 (9)
C31	0.0186 (12)	0.0183 (12)	0.0208 (13)	0.0048 (10)	0.0073 (10)	−0.0003 (10)
C32	0.0258 (14)	0.0177 (13)	0.0292 (15)	0.0023 (11)	0.0139 (12)	−0.0011 (11)
C33	0.0154 (13)	0.0143 (12)	0.0498 (18)	0.0020 (11)	0.0100 (12)	−0.0054 (12)
C34	0.0159 (13)	0.0186 (13)	0.0440 (17)	0.0058 (11)	−0.0050 (12)	−0.0020 (12)
C35	0.0170 (12)	0.0170 (12)	0.0283 (14)	0.0068 (10)	0.0009 (11)	0.0033 (10)
C36	0.0294 (14)	0.0246 (14)	0.0238 (14)	0.0121 (12)	0.0061 (11)	0.0017 (11)
C37	0.0368 (16)	0.0221 (14)	0.0245 (14)	0.0161 (12)	0.0101 (12)	0.0045 (11)
C38	0.0269 (14)	0.0196 (13)	0.0313 (15)	0.0064 (11)	0.0082 (12)	−0.0033 (11)
C39	0.0290 (14)	0.0234 (14)	0.0259 (14)	0.0135 (12)	0.0012 (11)	−0.0013 (11)
C40	0.0378 (16)	0.0251 (14)	0.0231 (14)	0.0145 (13)	0.0091 (12)	0.0051 (11)
C41	0.0280 (15)	0.0282 (15)	0.0259 (15)	0.0083 (12)	0.0102 (12)	0.0002 (11)
Li1	0.023 (2)	0.022 (2)	0.025 (2)	0.0119 (19)	0.0070 (18)	−0.0009 (18)
N1	0.0184 (10)	0.0162 (10)	0.0232 (11)	0.0076 (9)	0.0032 (9)	0.0029 (8)
N2	0.0159 (10)	0.0184 (10)	0.0151 (10)	0.0085 (9)	0.0044 (8)	0.0024 (8)
P1	0.0142 (3)	0.0118 (3)	0.0133 (3)	0.0053 (2)	0.0040 (2)	0.0011 (2)
P2	0.0119 (3)	0.0115 (3)	0.0130 (3)	0.0039 (2)	0.0028 (2)	0.0008 (2)
S1	0.0183 (3)	0.0199 (3)	0.0171 (3)	0.0095 (3)	0.0069 (2)	0.0020 (2)
S2	0.0169 (3)	0.0176 (3)	0.0135 (3)	0.0059 (2)	0.0025 (2)	−0.0013 (2)

C1—N1	1.334 (3)	C23—P2	1.712 (2)
C1—C2	1.386 (4)	C23—P1	1.716 (2)
C1—H1	0.9500	C23—H23	0.9500
C2—C3	1.383 (4)	C24—C25	1.388 (3)
C2—H2	0.9500	C24—C29	1.394 (3)
C3—C4	1.375 (4)	C24—P2	1.824 (2)
C3—H3	0.9500	C25—C26	1.392 (3)
C4—C5	1.398 (3)	C25—H25	0.9500
C4—H4	0.9500	C26—C27	1.386 (3)
C5—N1	1.349 (3)	C26—H26	0.9500
C5—C6	1.490 (3)	C27—C28	1.380 (3)
C6—N2	1.354 (3)	C27—H27	0.9500
C6—C7	1.393 (3)	C28—C29	1.383 (3)
C7—C8	1.382 (4)	C28—H28	0.9500
C7—H7	0.9500	C29—H29	0.9500
C8—C9	1.379 (4)	C30—C35	1.396 (3)
C8—H8	0.9500	C30—C31	1.398 (3)
C9—C10	1.382 (3)	C30—P2	1.825 (2)
C9—H9	0.9500	C31—C32	1.382 (3)
C10—N2	1.336 (3)	C31—H31	0.9500
C10—H10	0.9500	C32—C33	1.389 (4)
C11—C12	1.394 (3)	C32—H32	0.9500
C11—C16	1.397 (3)	C33—C34	1.383 (4)
C11—P1	1.828 (2)	C33—H33	0.9500
C12—C13	1.389 (3)	C34—C35	1.397 (3)
C12—H12	0.9500	C34—H34	0.9500
C13—C14	1.386 (4)	C35—H35	0.9500
C13—H13	0.9500	C36—C41	1.377 (4)
C14—C15	1.385 (4)	C36—C37	1.389 (4)
C14—H14	0.9500	C36—H36	0.9500
C15—C16	1.388 (3)	C37—C38	1.391 (4)
C15—H15	0.9500	C37—H37	0.9500
C16—H16	0.9500	C38—C39	1.383 (4)
C17—C22	1.390 (3)	C38—H38	0.9500
C17—C18	1.398 (3)	C39—C40	1.378 (4)
C17—P1	1.821 (2)	C39—H39	0.9500
C18—C19	1.390 (3)	C40—C41	1.392 (4)
C18—H18	0.9500	C40—H40	0.9500
C19—C20	1.385 (4)	C41—H41	0.9500
C19—H19	0.9500	Li1—N1	2.030 (5)
C20—C21	1.381 (4)	Li1—N2	2.035 (5)
C20—H20	0.9500	Li1—S2	2.420 (4)
C21—C22	1.387 (3)	Li1—S1	2.441 (4)
C21—H21	0.9500	P1—S1	1.9939 (9)
C22—H22	0.9500	P2—S2	2.0155 (8)
N1—C1—C2	123.4 (3)	C27—C26—C25	119.9 (2)
N1—C1—H1	118.3	C27—C26—H26	120.0
C2—C1—H1	118.3	C25—C26—H26	120.0
C3—C2—C1	118.1 (3)	C28—C27—C26	120.1 (2)
C3—C2—H2	121.0	C28—C27—H27	120.0
C1—C2—H2	121.0	C26—C27—H27	120.0
C4—C3—C2	119.6 (2)	C27—C28—C29	120.0 (2)
C4—C3—H3	120.2	C27—C28—H28	120.0
C2—C3—H3	120.2	C29—C28—H28	120.0
C3—C4—C5	119.0 (2)	C28—C29—C24	120.8 (2)
C3—C4—H4	120.5	C28—C29—H29	119.6
C5—C4—H4	120.5	C24—C29—H29	119.6
N1—C5—C4	121.7 (2)	C35—C30—C31	119.0 (2)
N1—C5—C6	115.5 (2)	C35—C30—P2	121.66 (18)
C4—C5—C6	122.8 (2)	C31—C30—P2	119.27 (18)
N2—C6—C7	121.8 (2)	C32—C31—C30	120.8 (2)
N2—C6—C5	115.4 (2)	C32—C31—H31	119.6
C7—C6—C5	122.8 (2)	C30—C31—H31	119.6
C8—C7—C6	119.2 (2)	C31—C32—C33	120.0 (2)
C8—C7—H7	120.4	C31—C32—H32	120.0
C6—C7—H7	120.4	C33—C32—H32	120.0
C9—C8—C7	119.4 (2)	C34—C33—C32	119.9 (2)
C9—C8—H8	120.3	C34—C33—H33	120.1
C7—C8—H8	120.3	C32—C33—H33	120.1
C8—C9—C10	118.0 (2)	C33—C34—C35	120.4 (2)
C8—C9—H9	121.0	C33—C34—H34	119.8
C10—C9—H9	121.0	C35—C34—H34	119.8
N2—C10—C9	124.2 (2)	C30—C35—C34	119.9 (2)
N2—C10—H10	117.9	C30—C35—H35	120.1
C9—C10—H10	117.9	C34—C35—H35	120.1
C12—C11—C16	118.7 (2)	C41—C36—C37	120.2 (3)
C12—C11—P1	122.17 (18)	C41—C36—H36	119.9
C16—C11—P1	118.92 (17)	C37—C36—H36	119.9
C13—C12—C11	120.5 (2)	C36—C37—C38	119.5 (2)
C13—C12—H12	119.8	C36—C37—H37	120.2
C11—C12—H12	119.8	C38—C37—H37	120.2
C14—C13—C12	120.1 (2)	C39—C38—C37	119.8 (3)
C14—C13—H13	119.9	C39—C38—H38	120.1
C12—C13—H13	119.9	C37—C38—H38	120.1
C15—C14—C13	120.0 (2)	C40—C39—C38	120.8 (3)
C15—C14—H14	120.0	C40—C39—H39	119.6
C13—C14—H14	120.0	C38—C39—H39	119.6
C14—C15—C16	119.9 (2)	C39—C40—C41	119.2 (3)
C14—C15—H15	120.1	C39—C40—H40	120.4
C16—C15—H15	120.1	C41—C40—H40	120.4
C15—C16—C11	120.7 (2)	C36—C41—C40	120.4 (3)
C15—C16—H16	119.6	C36—C41—H41	119.8
C11—C16—H16	119.6	C40—C41—H41	119.8
C22—C17—C18	118.9 (2)	N1—Li1—N2	81.54 (17)
C22—C17—P1	121.50 (18)	N1—Li1—S2	121.2 (2)
C18—C17—P1	119.61 (18)	N2—Li1—S2	119.1 (2)
C19—C18—C17	120.4 (2)	N1—Li1—S1	101.41 (18)
C19—C18—H18	119.8	N2—Li1—S1	114.67 (19)
C17—C18—H18	119.8	S2—Li1—S1	114.03 (17)
C20—C19—C18	119.6 (2)	C1—N1—C5	118.2 (2)
C20—C19—H19	120.2	C1—N1—Li1	127.7 (2)
C18—C19—H19	120.2	C5—N1—Li1	113.6 (2)
C21—C20—C19	120.6 (2)	C10—N2—C6	117.5 (2)
C21—C20—H20	119.7	C10—N2—Li1	128.9 (2)
C19—C20—H20	119.7	C6—N2—Li1	113.5 (2)
C20—C21—C22	119.7 (2)	C23—P1—C17	108.28 (11)
C20—C21—H21	120.2	C23—P1—C11	109.88 (11)
C22—C21—H21	120.2	C17—P1—C11	102.43 (10)
C21—C22—C17	120.8 (2)	C23—P1—S1	115.53 (9)
C21—C22—H22	119.6	C17—P1—S1	109.04 (8)
C17—C22—H22	119.6	C11—P1—S1	110.84 (8)
P2—C23—P1	127.35 (14)	C23—P2—C24	103.93 (11)
P2—C23—H23	116.3	C23—P2—C30	112.13 (11)
P1—C23—H23	116.3	C24—P2—C30	101.49 (10)
C25—C24—C29	118.9 (2)	C23—P2—S2	120.48 (8)
C25—C24—P2	122.51 (18)	C24—P2—S2	109.57 (8)
C29—C24—P2	118.57 (17)	C30—P2—S2	107.53 (8)
C24—C25—C26	120.4 (2)	P1—S1—Li1	105.29 (10)
C24—C25—H25	119.8	P2—S2—Li1	94.62 (11)
C26—C25—H25	119.8
N1—C1—C2—C3	2.9 (4)	S2—Li1—N1—C1	−63.8 (3)
C1—C2—C3—C4	−1.8 (4)	S1—Li1—N1—C1	63.6 (3)
C2—C3—C4—C5	−0.5 (4)	N2—Li1—N1—C5	5.4 (2)
C3—C4—C5—N1	2.0 (3)	S2—Li1—N1—C5	124.3 (2)
C3—C4—C5—C6	−178.4 (2)	S1—Li1—N1—C5	−108.24 (19)
N1—C5—C6—N2	6.6 (3)	C9—C10—N2—C6	0.4 (3)
C4—C5—C6—N2	−173.0 (2)	C9—C10—N2—Li1	−176.6 (2)
N1—C5—C6—C7	−172.6 (2)	C7—C6—N2—C10	−0.2 (3)
C4—C5—C6—C7	7.8 (3)	C5—C6—N2—C10	−179.4 (2)
N2—C6—C7—C8	−0.4 (4)	C7—C6—N2—Li1	177.3 (2)
C5—C6—C7—C8	178.8 (2)	C5—C6—N2—Li1	−2.0 (3)
C6—C7—C8—C9	0.8 (4)	N1—Li1—N2—C10	175.4 (2)
C7—C8—C9—C10	−0.6 (4)	S2—Li1—N2—C10	54.4 (3)
C8—C9—C10—N2	0.0 (4)	S1—Li1—N2—C10	−85.8 (3)
C16—C11—C12—C13	−1.6 (3)	N1—Li1—N2—C6	−1.7 (2)
P1—C11—C12—C13	173.52 (18)	S2—Li1—N2—C6	−122.8 (2)
C11—C12—C13—C14	0.8 (4)	S1—Li1—N2—C6	97.0 (2)
C12—C13—C14—C15	0.6 (4)	P2—C23—P1—C17	−137.84 (16)
C13—C14—C15—C16	−1.1 (4)	P2—C23—P1—C11	111.03 (17)
C14—C15—C16—C11	0.2 (4)	P2—C23—P1—S1	−15.3 (2)
C12—C11—C16—C15	1.2 (3)	C22—C17—P1—C23	7.2 (2)
P1—C11—C16—C15	−174.16 (18)	C18—C17—P1—C23	−175.07 (18)
C22—C17—C18—C19	0.3 (3)	C22—C17—P1—C11	123.3 (2)
P1—C17—C18—C19	−177.44 (18)	C18—C17—P1—C11	−59.0 (2)
C17—C18—C19—C20	0.4 (4)	C22—C17—P1—S1	−119.22 (18)
C18—C19—C20—C21	−1.4 (4)	C18—C17—P1—S1	58.5 (2)
C19—C20—C21—C22	1.6 (4)	C12—C11—P1—C23	−115.8 (2)
C20—C21—C22—C17	−0.9 (4)	C16—C11—P1—C23	59.4 (2)
C18—C17—C22—C21	0.0 (3)	C12—C11—P1—C17	129.29 (19)
P1—C17—C22—C21	177.68 (19)	C16—C11—P1—C17	−55.5 (2)
C29—C24—C25—C26	−0.4 (4)	C12—C11—P1—S1	13.1 (2)
P2—C24—C25—C26	178.70 (19)	C16—C11—P1—S1	−171.73 (16)
C24—C25—C26—C27	−0.2 (4)	P1—C23—P2—C24	−178.69 (15)
C25—C26—C27—C28	0.5 (4)	P1—C23—P2—C30	72.50 (19)
C26—C27—C28—C29	−0.2 (4)	P1—C23—P2—S2	−55.57 (19)
C27—C28—C29—C24	−0.4 (4)	C25—C24—P2—C23	121.7 (2)
C25—C24—C29—C28	0.7 (4)	C29—C24—P2—C23	−59.1 (2)
P2—C24—C29—C28	−178.4 (2)	C25—C24—P2—C30	−121.7 (2)
C35—C30—C31—C32	−0.6 (3)	C29—C24—P2—C30	57.4 (2)
P2—C30—C31—C32	−177.49 (18)	C25—C24—P2—S2	−8.3 (2)
C30—C31—C32—C33	−0.5 (4)	C29—C24—P2—S2	170.88 (17)
C31—C32—C33—C34	0.9 (4)	C35—C30—P2—C23	2.4 (2)
C32—C33—C34—C35	−0.1 (4)	C31—C30—P2—C23	179.20 (18)
C31—C30—C35—C34	1.4 (3)	C35—C30—P2—C24	−107.9 (2)
P2—C30—C35—C34	178.17 (19)	C31—C30—P2—C24	68.8 (2)
C33—C34—C35—C30	−1.0 (4)	C35—C30—P2—S2	137.06 (18)
C41—C36—C37—C38	0.9 (4)	C31—C30—P2—S2	−46.16 (19)
C36—C37—C38—C39	−0.8 (4)	C23—P1—S1—Li1	45.66 (14)
C37—C38—C39—C40	0.0 (4)	C17—P1—S1—Li1	167.84 (13)
C38—C39—C40—C41	0.6 (4)	C11—P1—S1—Li1	−80.14 (13)
C37—C36—C41—C40	−0.2 (4)	N1—Li1—S1—P1	−156.15 (13)
C39—C40—C41—C36	−0.6 (4)	N2—Li1—S1—P1	118.00 (18)
C2—C1—N1—C5	−1.6 (4)	S2—Li1—S1—P1	−24.21 (19)
C2—C1—N1—Li1	−173.1 (2)	C23—P2—S2—Li1	63.07 (14)
C4—C5—N1—C1	−0.9 (3)	C24—P2—S2—Li1	−176.55 (13)
C6—C5—N1—C1	179.4 (2)	C30—P2—S2—Li1	−67.04 (13)
C4—C5—N1—Li1	171.8 (2)	N1—Li1—S2—P2	100.7 (2)
C6—C5—N1—Li1	−7.9 (3)	N2—Li1—S2—P2	−161.3 (2)
N2—Li1—N1—C1	177.2 (2)	S1—Li1—S2—P2	−20.83 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···S1	0.95	2.86	3.367 (2)	114
C25—H25···S2	0.95	2.82	3.332 (2)	115
C1—H1···Cg6	0.95	2.77	3.710 (3)	172
C21—H21···Cg6i	0.95	2.70	3.632 (3)	166
C28—H28···Cg7ii	0.95	2.93	3.654 (3)	134
C37—H37···Cg3iii	0.95	2.80	3.634 (3)	147

Table 1

Hydrogen-bond geometry (Å, °)

Cg3, Cg6 and Cg7 are the centroids of the C11–C16, C30–C35 and C36–C41 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯S1	0.95	2.86	3.367 (2)	114
C25—H25⋯S2	0.95	2.82	3.332 (2)	115
C1—H1⋯Cg6	0.95	2.77	3.710 (3)	172
C21—H21⋯Cg6i	0.95	2.70	3.632 (3)	166
C28—H28⋯Cg7ii	0.95	2.93	3.654 (3)	134
C37—H37⋯Cg3iii	0.95	2.80	3.634 (3)	147

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