N-(Diphenyl­selenio)diphenyl­sulfimidium tetraphenyl­borate

Aucott, S.M.; Dale, S.H.; Elsegood, M.R.J.; Gilby, L.M.; Holmes, K.E.; Kelly, P.F.

doi:10.1107/S0108270104033505

organic compounds

STRUCTURAL
CHEMISTRY

ISSN: 2053-2296

Volume 61| Part 2| February 2005| Pages o112-o113

doi:10.1107/S0108270104033505

N-(Diphenylselenio)diphenylsulfimidium tetraphenylborate

Stephen M. Aucott,^a Sophie H. Dale,^a Mark R. J. Elsegood,^a Liam M. Gilby,^a Kathryn E. Holmes ^a and Paul F. Kelly ^a ^*

^aChemistry Department, Loughborough University, Loughborough, Leicestershire LE11 3TU, England
^*Correspondence e-mail: p.f.kelly@lboro.ac.uk

(Received 11 November 2004; accepted 16 December 2004; online 22 January 2005)

The title compound, C₂₄H₂₀NSSe⁺·C₂₄H₂₀B⁻, exhibits disorder (S/Se scrambling) of the chalcogen sites within the S—N—Se triad. Similar disorder was observed in the bromide salt [Aucott, Bailey, Elsegood, Gilby, Holmes, Kelly, Papageorgiou & Pedrón-Haba (2004 ). New J. Chem. pp. 959–966]. The S—N and Se—N bond lengths are 1.6735 (15) and 1.8045 (14) Å, respectively. Whereas the chalcogens in the bromide salt are involved in S⋯Br and Se⋯Br interactions of very similar distances, the scrambled S and Se sites in the title compound are involved in distinct non-bonded interactions. The site predominantly occupied by sulfur is involved in C—H⋯S/Se interactions, while the site predominantly occupied by selenium is involved in Se/S⋯π interactions.

Comment

Until our recent investigations extending the chemistry of homochalcogen cationic sulfimide derivatives, such as [Ph₂SNSPh₂]⁺, to mixed chalcogen species had not been reported. In synthesizing and fully characterizing [Ph₂SNSePh₂]Br and [1,4-(PhSNSePh₂)₂C₆H₄][BPh₄]₂, we were able to obtain the first insight into the structure of N-seleniosulfimidium systems, which represent new additions to the general family of mixed S/Se—N compounds (Aucott et al., 2004).

In the case of [Ph₂SNSePh₂]Br (Aucott et al., 2004), X-ray crystallography revealed Se—N and S—N bond lengths of 1.832 (3) and 1.678 (3) Å, respectively, with an S—N—Se angle of 107.61 (15)°, although disorder within the system means that there is some scrambling of the S and Se sites, the refined major occupancy of the disordered chalcogen sites being 83.2 (2)%. This suggests that the true Se—N distance in the system is actually longer than that quoted, which, intriguingly, places the bond within the range normally associated with Se—N single bonds. By way of illustration, an Se—N length of 1.844 (3) Å has been reported for (Me₃SiNSN)₂Se (Konu et al., 2002 ), while single-bond lengths of 1.827 (5) and 1.869 (2) Å have also been observed in OSN–Se–NSO (Haas et al., 1991 ) and (Me₃Si)₂N–Se–N(SiMe₃)₂ (Björgvinsson et al., 1990 ), respectively.

In the case of [1,4-(PhSNSePh₂)₂C₆H₄][BPh₄]₂ (Aucott et al., 2004), X-ray crystallography revealed a structure with no disorder (but with an associated reduction in symmetry) and an Se—N bond length of 1.814 (2) Å. This again is long, more akin to an Se—N single bond, albeit shorter than in [Ph₂SNSePh₂]Br. In order to shed further light on these systems, we have now prepared and crystallized the title compound, (I) (Fig. 1).

Compound (I) crystallizes in a centrosymmetric space group with one complete formula unit in the asymmetric unit. The structure exhibits scrambling of the chalcogen sites, as was observed in the bromide salt [refined occupancies 85.21 (11):14.79 (11)%]. In (I), the Se—N and S—N bond lengths are 1.8045 (14) and 1.6735 (15) Å, respectively, with an S—N—Se angle of 109.71 (8)° (Table 1). The Se—N bond length is clearly shorter and the bond angle wider than was observed in the disordered bromide salt.

There are non-bonded interactions between the cations and anions in both the bromide salt and in (I). In the bromide salt, cation–anion interactions take the form of non-bonded contacts between the Br⁻ anion and the chalcogen atoms. There are three interactions: S1⋯Br1 of 3.4550 (8) Å, Se1⋯Br1 of 3.3208 (5) Å and Se1⋯Br1ⁱ of 3.3993 (5) Å [symmetry code: (i) 1 − x, 1 − y, −z]. In the following discussion of the intermolecular interactions in (I), only those of the major disorder component will be highlighted (the same interactions apply to the minor disorder component, with Se and S atoms interchanged).

Atom S1 is involved in a C—H⋯S interaction (C36—H36⋯S1), with C⋯S 3.8276 (19) Å, H⋯S 2.92 Å and C—H⋯S 161°. Atom Se1 participates in an Se⋯π interaction with one phenyl ring of the BPh₄⁻ anion, with atom Se1 lying 3.1503 (9) Å from the least-squares plane of the aromatic ring containing atoms C43–C48 (Fig. 1). The Se⋯C distances between atom Se1 and the C atoms of the phenyl ring range from 3.3327 (18) (C46) to 3.6239 (16) Å (C43), averaging 3.462 (11) Å.

A search of the Cambridge Structural Database (Version 5.25, November 2003 update; Allen, 2002 ; Fletcher et al., 1996 ) for Se⋯π interactions (with search conditions for an Se atom having contacts in the range 3–4 Å with all six C atoms of a phenyl ring) identified 33 structures containing such interactions. The Se⋯C contact distances (within the search limits) are in the range 3.335–3.999 Å, averaging 3.75 (13) Å, indicating the Se⋯C distances observed in (I) to be relatively short. It is interesting to note that, although six of the structures contain the PPh₄⁺ cation (see, for example, Ansari et al., 1989 ; Heuer et al., 1988 ), compound (I) represents the first example of a compound containing close Se⋯π interactions with a BPh₄⁻ anion.

Figure 1
A view of (I

), showing the atom-labelling scheme and the C—H⋯S and Se⋯π cation–anion interactions. Displacement ellipsoids are drawn at the 50% probability level. The minor disorder component and H atoms (except H36) have been omitted for clarity. Non-bonded interactions are shown as dashed lines.

Experimental

A precipitate of [Ph₂SNSePh₂][BPh₄] was prepared by the addition of Na[BPh₄] to a solution of [Ph₂SNSePh₂]Br (Aucott et al., 2004) in methanol. Dissolution of the precipitate in CH₂Cl₂ and crystallization by slow vapour diffusion of diethyl ether into this solution produced X-ray quality colourless crystals of (I).

Crystal data

C₂₄H₂₀NSSe⁺·C₂₄H₂₀B⁻
M_r = 752.64
Monoclinic, P2₁/c
a = 12.2627 (11) Å
b = 27.860 (2) Å
c = 12.2402 (11) Å
β = 114.438 (2)°
V = 3807.1 (6) Å³
Z = 4
D_x = 1.313 Mg m⁻³
Mo Kα radiation
Cell parameters from 16 364 reflections
θ = 2.3–28.9°
μ = 1.08 mm⁻¹
T = 150 (2) K
Block, colourless
0.67 × 0.26 × 0.24 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Thin-slice ω scans
Absorption correction: multi-scan(SADABS; Sheldrick, 2003 )T_min = 0.532, T_max = 0.782
32 563 measured reflections
9135 independent reflections
7611 reflections with I > 2σ(I)
R_int = 0.078
θ_max = 28.9°
h = −16 → 15
k = −37 → 37
l = −16 → 16

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.116
S = 1.02
9135 reflections
470 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.077P)²] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.93 e Å⁻³
Δρ_min = −0.94 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Se1—N1	1.8045 (14)
Se1—C1	1.9066 (18)
Se1—C7	1.9231 (18)
S1—N1	1.6735 (15)
S1—C13	1.8088 (18)
S1—C19	1.8249 (17)

S1—N1—Se1	109.71 (8)

Compound (I) exhibits disorder with respect to the positions of the S and Se atoms, and this scrambling was successfully modelled with minor disorder atoms S1X and Se1X occupying identical positions to Se1 and S1, respectively. The anisotropic displacement parameters of the pairs S1/Se1X and Se1/S1X were constrained to be identical. This disorder modelling resulted in a reduction of 0.018 in the value of R₁ and in final refined occupancies of 85.21 (11):14.79 (11)%. H atoms were placed in geometrically calculated positions (C—H = 0.95 Å) and refined using a riding model, with U_iso(H) = 1.2U_eq(C). The data set was truncated at 2θ = 55°, as only statistically insignificant data were present above this limit.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2000 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S0108270104033505/bm1600sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S0108270104033505/bm1600Isup2.hkl

Comment top

Until our recent investigations, extending the chemistry of homochalcogen cationic sulfimide derivatives, such as [Ph₂SNSPh₂]⁺, to mixed chalcogen species had not been reported. In synthesizing and fully characterizing [Ph₂SNSePh₂]Br and [1,4-(PhSNSePh₂)₂C₆H₄][BPh₄]₂, we were able to obtain the first insight into the structure of N-seleniosulfimidium systems, which represent new additions to the general family of mixed S/Se—N compounds (Aucott et al., 2004).

In the case of [Ph₂SNSePh₂]Br (Aucott et al., 2004), X-ray crystallography revealed Se—N and S—N bond lengths of 1.832 (3) and 1.678 (3) Å, respectively, with an S—N—Se angle of 107.61 (15)°, although disorder within the system means that there is some scrambling of the S and Se sites, the refined major occupancy of the disordered chalcogen sites being 83.2 (2)%. This suggests that the true Se—N distance in the system is actually longer than that quoted, which, intriguingly, places the bond within the range normally associated with Se—N single bonds. By way of illustration, an Se—N length of 1.844 (3) Å has been noted for (Me₃SiNSN)₂Se (Konu et al., 2003), while single-bond lengths of 1.827 (5) and 1.869 (2) Å have also been observed in OSN—Se—NSO (Haas et al., 1991) and (Me₃Si)₂N—Se—N(SiMe₃)₂ (Björgvinsson et al., 1990), respectively.

In the case of [1,4-(PhSNSePh₂)₂C₆H₄][BPh₄]₂ (Aucott et al., 2004), X-ray crystallography revealed a structure with no disorder (but with an associated reduction in symmetry) and an Se—N bond length of 1.814 (2) Å. This again is long, more akin to an Se—N single bond, albeit shorter than in [Ph₂SNSePh₂]Br. In order to shed further light on these systems, we have now prepared and crystallized the title compound, (I) (Fig. 1).

Compound (I) crystallizes in a centrosymmetric space group with one complete formula unit in the asymmetric unit. The structure exhibits scrambling of the chalcogen sites, as was observed in the bromide salt [refined occupancies 85.21 (11): 14.79 (11)%]. In (I), the Se—N and S—N bond lengths are 1.8045 (14) and 1.6735 (15) Å, respectively, with an S—N—Se angle of 109.71 (8)° (Table 1). The Se—N bond length is clearly shorter, and the bond angle is wider, than were observed in the disordered bromide salt.

There are non-bonded interactions between the cations and anions in both the bromide salt and in (I). In the bromide salt, cation–anion interactions take the form of non-bonded contacts between the Br⁻ anion and the chalcogen atoms. There are three interactions of 3.4550 (8) Å (S1···Br1), 3.3208 (5) Å (Se1···Br1) and 3.3993 (5) Å [Se1···Br1ⁱ; symmetry code: (i) 1 − x, 1 − y, −z]. In the following discussion of the intermolecular interactions in (I), only those of the major disorder component will be highlighted (the same interactions apply to the minor disorder component, with Se and S atoms interchanged).

Atom S1 is involved in a C—H···S interaction (C36—H36···S1), with C···S 3.8276 (19) Å, H···S 2.92 Å and C—H···S 161°. Atom Se1 participates in an Se···π interaction with one phenyl ring of the BPh₄⁻ anion, with atom Se1 lying 3.1503 (9) Å from the least-squares plane of the aromatic ring containing atoms C43–C48 (Fig. 1). The Se···C distances between atom Se1 and the C atoms of the phenyl ring range from 3.3327 (18) Å (C46) to 3.6239 (16) Å (C43), averaging 3.462 (11) Å.

A search of the Cambridge Structural Database (Allen, 2002; Fletcher et al., 1996; Version 5.25, November 2003 update) for Se···π interactions (with search conditions for an Se atom having contacts in the range 3–4 Å with all six C atoms of a phenyl ring) identified 33 structures containing such interactions. The Se···C contact distances (within the search limits) range from 3.335–3.999 Å, averaging 3.75 (13) Å, indicating the Se···C distances observed in (I) to be relatively short. It is interesting to note that, although six of the structures contain the PPh₄⁺ cation (for example, Ansari et al., 1989; Heuer et al., 1988), compound (I) represents the first example of a compound containing close Se···π interactions with a BPh₄⁻ anion.

Experimental top

A precipitate of [Ph₂SNSePh₂][BPh₄] was prepared by the addition of Na[BPh₄] to a solution of [Ph₂SNSePh₂]Br (Aucott et al., 2004) in methanol. Dissolution of the precipitate in CH₂Cl₂ and crystallization by slow vapour diffusion of diethyl ether into this solution produced X-ray quality colourless crystals of (I).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Figures top

Fig. 1. A view of (I), showing the atom-labelling scheme and the C—H···S and Se···π cation–anion interactions. Displacement ellipsoids are drawn at the 50% probability level. The minor disorder component and H atoms except H36 have been removed for clarity. Non-bonded interactions are shown as dashed lines.

N-(Diphenylselenio)diphenylsulfimidium tetraphenylborate top

Crystal data top

C₂₄H₂₀NSSe⁺·C₂₄H₂₀B⁻	F(000) = 1560
M_r = 752.64	D_x = 1.313 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 16364 reflections
a = 12.2627 (11) Å	θ = 2.3–28.9°
b = 27.860 (2) Å	µ = 1.08 mm⁻¹
c = 12.2402 (11) Å	T = 150 K
β = 114.438 (2)°	Block, colourless
V = 3807.1 (6) Å³	0.67 × 0.26 × 0.24 mm
Z = 4

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	9135 independent reflections
Radiation source: sealed tube	7611 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.078
thin–slice ω scans	θ_max = 28.9°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −16→15
T_min = 0.532, T_max = 0.782	k = −37→37
32563 measured reflections	l = −16→16

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.043	H-atom parameters constrained
wR(F²) = 0.116	w = 1/[σ²(F_o²) + (0.077P)²] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
9135 reflections	Δρ_max = 0.93 e Å⁻³
470 parameters	Δρ_min = −0.94 e Å⁻³
0 restraints

Crystal data top

C₂₄H₂₀NSSe⁺·C₂₄H₂₀B⁻	V = 3807.1 (6) Å³
M_r = 752.64	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.2627 (11) Å	µ = 1.08 mm⁻¹
b = 27.860 (2) Å	T = 150 K
c = 12.2402 (11) Å	0.67 × 0.26 × 0.24 mm
β = 114.438 (2)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	9135 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	7611 reflections with I > 2σ(I)
T_min = 0.532, T_max = 0.782	R_int = 0.078
32563 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 1.02	Δρ_max = 0.93 e Å⁻³
9135 reflections	Δρ_min = −0.94 e Å⁻³
470 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)
Se1	0.289137 (16)	0.089958 (7)	0.231327 (16)	0.02176 (8)	0.8521 (11)
S1	0.33708 (3)	0.173346 (13)	0.12437 (3)	0.02625 (13)	0.8521 (11)
Se1X	0.33708 (3)	0.173346 (13)	0.12437 (3)	0.02625 (13)	0.1479 (11)
S1X	0.289137 (16)	0.089958 (7)	0.231327 (16)	0.02176 (8)	0.1479 (11)
N1	0.24581 (13)	0.12593 (5)	0.09732 (13)	0.0253 (3)
C1	0.27774 (16)	0.02817 (6)	0.16044 (16)	0.0252 (4)
C2	0.37317 (16)	−0.00256 (7)	0.21357 (17)	0.0293 (4)
H2	0.4400	0.0064	0.2848	0.035*
C3	0.36941 (19)	−0.04702 (7)	0.1604 (2)	0.0369 (5)
H3	0.4340	−0.0689	0.1958	0.044*
C4	0.2727 (2)	−0.05938 (7)	0.05686 (19)	0.0383 (5)
H4	0.2713	−0.0897	0.0206	0.046*
C5	0.1770 (2)	−0.02811 (8)	0.00483 (19)	0.0397 (5)
H5	0.1108	−0.0370	−0.0670	0.048*
C6	0.17750 (18)	0.01591 (7)	0.05693 (17)	0.0326 (4)
H6	0.1114	0.0372	0.0232	0.039*
C7	0.13716 (16)	0.08872 (6)	0.24223 (16)	0.0242 (4)
C8	0.11264 (17)	0.05052 (7)	0.30142 (17)	0.0313 (4)
H8	0.1671	0.0245	0.3303	0.038*
C9	0.00699 (18)	0.05112 (8)	0.31761 (17)	0.0363 (5)
H9	−0.0111	0.0254	0.3582	0.044*
C10	−0.07210 (18)	0.08918 (7)	0.27473 (19)	0.0336 (4)
H10	−0.1445	0.0893	0.2854	0.040*
C11	−0.04603 (18)	0.12709 (7)	0.2163 (2)	0.0342 (4)
H11	−0.1002	0.1532	0.1879	0.041*
C12	0.05967 (17)	0.12703 (7)	0.19893 (18)	0.0295 (4)
H12	0.0778	0.1528	0.1583	0.035*
C13	0.23038 (16)	0.22171 (6)	0.06433 (17)	0.0253 (4)
C14	0.15332 (17)	0.22429 (8)	−0.05694 (17)	0.0338 (4)
H14	0.1585	0.2015	−0.1124	0.041*
C15	0.06907 (19)	0.26072 (8)	−0.0951 (2)	0.0421 (5)
H15	0.0162	0.2630	−0.1776	0.051*
C16	0.0610 (2)	0.29370 (8)	−0.0146 (2)	0.0448 (5)
H16	0.0029	0.3186	−0.0418	0.054*
C17	0.1374 (2)	0.29054 (8)	0.1052 (2)	0.0473 (6)
H17	0.1311	0.3132	0.1604	0.057*
C18	0.2237 (2)	0.25454 (7)	0.14622 (19)	0.0374 (5)
H18	0.2769	0.2526	0.2287	0.045*
C19	0.38822 (15)	0.16907 (6)	0.00429 (15)	0.0227 (3)
C20	0.35373 (16)	0.13136 (7)	−0.07619 (17)	0.0280 (4)
H20	0.3032	0.1067	−0.0698	0.034*
C21	0.39442 (17)	0.13010 (7)	−0.16696 (18)	0.0320 (4)
H21	0.3697	0.1049	−0.2243	0.038*
C22	0.47047 (18)	0.16536 (7)	−0.17381 (19)	0.0331 (4)
H22	0.4985	0.1641	−0.2354	0.040*
C23	0.50598 (18)	0.20251 (7)	−0.09136 (19)	0.0343 (4)
H23	0.5588	0.2265	−0.0963	0.041*
C24	0.46483 (16)	0.20489 (7)	−0.00153 (17)	0.0288 (4)
H24	0.4885	0.2305	0.0549	0.035*
B1	0.69359 (16)	0.11931 (7)	0.46059 (17)	0.0197 (4)
C25	0.80926 (15)	0.10753 (6)	0.58713 (16)	0.0229 (3)
C26	0.92322 (16)	0.10183 (7)	0.58713 (18)	0.0281 (4)
H26	0.9294	0.1006	0.5123	0.034*
C27	1.02734 (18)	0.09786 (7)	0.6921 (2)	0.0365 (5)
H27	1.1025	0.0936	0.6882	0.044*
C28	1.02092 (19)	0.10020 (9)	0.8026 (2)	0.0441 (6)
H28	1.0917	0.0982	0.8747	0.053*
C29	0.9104 (2)	0.10550 (9)	0.80663 (19)	0.0441 (5)
H29	0.9052	0.1071	0.8819	0.053*
C30	0.80718 (17)	0.10846 (8)	0.70098 (17)	0.0326 (4)
H30	0.7321	0.1112	0.7059	0.039*
C31	0.67536 (15)	0.07737 (6)	0.35999 (16)	0.0223 (3)
C32	0.73561 (17)	0.03324 (6)	0.38654 (18)	0.0283 (4)
H32	0.7875	0.0265	0.4676	0.034*
C33	0.72287 (19)	−0.00113 (7)	0.2995 (2)	0.0367 (5)
H33	0.7654	−0.0306	0.3220	0.044*
C34	0.64870 (19)	0.00741 (8)	0.1806 (2)	0.0396 (5)
H34	0.6427	−0.0153	0.1205	0.047*
C35	0.58347 (18)	0.04939 (8)	0.15057 (18)	0.0363 (5)
H35	0.5305	0.0554	0.0695	0.044*
C36	0.59524 (16)	0.08301 (7)	0.23907 (17)	0.0272 (4)
H36	0.5469	0.1110	0.2167	0.033*
C37	0.72381 (15)	0.17290 (6)	0.42128 (16)	0.0227 (3)
C38	0.71012 (17)	0.18716 (7)	0.30633 (18)	0.0329 (4)
H38	0.6814	0.1644	0.2429	0.039*
C39	0.7372 (2)	0.23370 (8)	0.2814 (2)	0.0411 (5)
H39	0.7248	0.2419	0.2019	0.049*
C40	0.78135 (19)	0.26754 (7)	0.3709 (2)	0.0418 (5)
H40	0.7998	0.2991	0.3541	0.050*
C41	0.79829 (19)	0.25463 (7)	0.4858 (2)	0.0396 (5)
H41	0.8297	0.2774	0.5491	0.048*
C42	0.76960 (17)	0.20851 (7)	0.50960 (17)	0.0302 (4)
H42	0.7817	0.2009	0.5894	0.036*
C43	0.56868 (14)	0.12058 (6)	0.48057 (14)	0.0203 (3)
C44	0.52693 (15)	0.07889 (7)	0.51494 (16)	0.0260 (4)
H44	0.5727	0.0503	0.5273	0.031*
C45	0.42113 (16)	0.07756 (8)	0.53185 (16)	0.0304 (4)
H45	0.3961	0.0484	0.5546	0.036*
C46	0.35266 (17)	0.11865 (8)	0.51555 (16)	0.0316 (4)
H46	0.2814	0.1181	0.5284	0.038*
C47	0.38977 (16)	0.16082 (7)	0.48010 (18)	0.0323 (4)
H47	0.3429	0.1891	0.4670	0.039*
C48	0.49601 (16)	0.16141 (7)	0.46385 (17)	0.0270 (4)
H48	0.5202	0.1906	0.4405	0.032*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Se1	0.02034 (12)	0.02423 (12)	0.02233 (12)	0.00008 (7)	0.01045 (8)	0.00259 (7)
S1	0.0259 (2)	0.0232 (2)	0.0344 (2)	0.00082 (14)	0.01725 (17)	0.00347 (14)
Se1X	0.0259 (2)	0.0232 (2)	0.0344 (2)	0.00082 (14)	0.01725 (17)	0.00347 (14)
S1X	0.02034 (12)	0.02423 (12)	0.02233 (12)	0.00008 (7)	0.01045 (8)	0.00259 (7)
N1	0.0227 (7)	0.0283 (8)	0.0237 (7)	−0.0057 (6)	0.0083 (6)	0.0042 (6)
C1	0.0291 (9)	0.0262 (8)	0.0254 (8)	−0.0010 (7)	0.0164 (7)	0.0036 (7)
C2	0.0240 (9)	0.0320 (9)	0.0337 (10)	0.0009 (7)	0.0139 (8)	0.0030 (8)
C3	0.0348 (10)	0.0322 (10)	0.0506 (12)	0.0071 (8)	0.0246 (10)	0.0037 (9)
C4	0.0517 (13)	0.0292 (10)	0.0452 (12)	−0.0027 (9)	0.0313 (10)	−0.0067 (9)
C5	0.0450 (12)	0.0376 (11)	0.0331 (10)	−0.0059 (9)	0.0128 (9)	−0.0079 (8)
C6	0.0330 (10)	0.0317 (10)	0.0295 (9)	0.0029 (8)	0.0092 (8)	0.0011 (8)
C7	0.0219 (8)	0.0301 (9)	0.0228 (8)	−0.0028 (7)	0.0114 (7)	−0.0016 (7)
C8	0.0260 (9)	0.0370 (10)	0.0306 (9)	0.0004 (8)	0.0116 (8)	0.0082 (8)
C9	0.0319 (10)	0.0481 (12)	0.0332 (10)	−0.0087 (9)	0.0181 (8)	0.0049 (9)
C10	0.0276 (10)	0.0443 (12)	0.0359 (10)	−0.0071 (8)	0.0202 (9)	−0.0077 (8)
C11	0.0310 (10)	0.0320 (10)	0.0469 (12)	0.0009 (8)	0.0235 (9)	−0.0049 (8)
C12	0.0283 (9)	0.0251 (9)	0.0397 (10)	−0.0017 (7)	0.0186 (8)	−0.0004 (7)
C13	0.0220 (8)	0.0235 (8)	0.0334 (9)	0.0020 (7)	0.0146 (7)	0.0036 (7)
C14	0.0318 (10)	0.0385 (11)	0.0310 (10)	0.0079 (9)	0.0128 (8)	0.0018 (8)
C15	0.0334 (11)	0.0500 (13)	0.0408 (11)	0.0152 (10)	0.0132 (9)	0.0112 (10)
C16	0.0401 (12)	0.0376 (12)	0.0638 (15)	0.0156 (9)	0.0285 (12)	0.0119 (10)
C17	0.0590 (15)	0.0348 (11)	0.0565 (14)	0.0104 (11)	0.0322 (12)	−0.0039 (10)
C18	0.0417 (12)	0.0339 (10)	0.0375 (11)	0.0016 (9)	0.0173 (9)	−0.0033 (8)
C19	0.0205 (8)	0.0236 (8)	0.0263 (8)	0.0023 (6)	0.0119 (7)	0.0030 (6)
C20	0.0251 (9)	0.0267 (9)	0.0364 (10)	−0.0022 (7)	0.0168 (8)	−0.0027 (7)
C21	0.0320 (10)	0.0330 (10)	0.0346 (10)	−0.0013 (8)	0.0173 (8)	−0.0068 (8)
C22	0.0341 (10)	0.0345 (10)	0.0399 (11)	0.0035 (8)	0.0246 (9)	0.0005 (8)
C23	0.0333 (10)	0.0301 (10)	0.0480 (12)	−0.0055 (8)	0.0254 (9)	0.0001 (8)
C24	0.0286 (9)	0.0244 (9)	0.0364 (10)	−0.0033 (7)	0.0163 (8)	−0.0023 (7)
B1	0.0189 (9)	0.0214 (9)	0.0224 (9)	−0.0011 (7)	0.0121 (7)	−0.0008 (7)
C25	0.0210 (8)	0.0209 (8)	0.0277 (9)	−0.0002 (6)	0.0110 (7)	0.0032 (7)
C26	0.0232 (9)	0.0289 (9)	0.0328 (10)	0.0016 (7)	0.0123 (8)	0.0017 (7)
C27	0.0208 (9)	0.0346 (10)	0.0497 (13)	0.0014 (8)	0.0102 (9)	0.0085 (9)
C28	0.0268 (10)	0.0546 (14)	0.0375 (11)	−0.0067 (10)	−0.0003 (9)	0.0154 (10)
C29	0.0365 (11)	0.0648 (15)	0.0262 (10)	−0.0094 (11)	0.0082 (9)	0.0104 (10)
C30	0.0251 (9)	0.0443 (11)	0.0285 (9)	−0.0040 (8)	0.0111 (8)	0.0048 (8)
C31	0.0195 (8)	0.0248 (8)	0.0278 (9)	−0.0037 (7)	0.0151 (7)	−0.0016 (7)
C32	0.0289 (9)	0.0241 (9)	0.0375 (10)	−0.0026 (7)	0.0194 (8)	−0.0003 (7)
C33	0.0372 (11)	0.0227 (9)	0.0595 (13)	−0.0053 (8)	0.0294 (10)	−0.0074 (9)
C34	0.0443 (12)	0.0371 (11)	0.0502 (13)	−0.0156 (9)	0.0324 (11)	−0.0200 (9)
C35	0.0351 (10)	0.0462 (12)	0.0302 (10)	−0.0129 (9)	0.0160 (8)	−0.0105 (9)
C36	0.0220 (9)	0.0325 (9)	0.0288 (9)	−0.0038 (7)	0.0121 (8)	−0.0038 (7)
C37	0.0174 (8)	0.0257 (9)	0.0277 (9)	0.0018 (6)	0.0121 (7)	0.0027 (7)
C38	0.0308 (10)	0.0372 (11)	0.0316 (10)	−0.0048 (8)	0.0139 (8)	0.0050 (8)
C39	0.0407 (11)	0.0429 (12)	0.0434 (12)	−0.0032 (10)	0.0212 (10)	0.0167 (9)
C40	0.0374 (11)	0.0280 (10)	0.0660 (15)	−0.0011 (9)	0.0275 (11)	0.0116 (10)
C41	0.0450 (12)	0.0252 (10)	0.0537 (13)	−0.0052 (9)	0.0255 (11)	−0.0051 (9)
C42	0.0346 (10)	0.0251 (9)	0.0346 (10)	−0.0010 (8)	0.0180 (8)	−0.0023 (7)
C43	0.0176 (7)	0.0255 (8)	0.0185 (7)	−0.0004 (6)	0.0082 (6)	−0.0013 (6)
C44	0.0207 (8)	0.0324 (9)	0.0253 (9)	−0.0001 (7)	0.0099 (7)	0.0055 (7)
C45	0.0242 (9)	0.0440 (11)	0.0250 (9)	−0.0051 (8)	0.0120 (7)	0.0062 (8)
C46	0.0222 (9)	0.0515 (12)	0.0262 (9)	−0.0053 (8)	0.0150 (7)	−0.0086 (8)
C47	0.0235 (9)	0.0364 (10)	0.0388 (10)	0.0021 (8)	0.0146 (8)	−0.0102 (8)
C48	0.0239 (9)	0.0270 (9)	0.0331 (9)	0.0009 (7)	0.0148 (8)	−0.0047 (7)

Geometric parameters (Å, º) top

Se1—N1	1.8045 (14)	C24—H24	0.9500
Se1—C1	1.9066 (18)	B1—C25	1.643 (3)
Se1—C7	1.9231 (18)	B1—C31	1.644 (2)
S1—N1	1.6735 (15)	B1—C43	1.648 (2)
S1—C13	1.8088 (18)	B1—C37	1.657 (2)
S1—C19	1.8249 (17)	C25—C30	1.404 (3)
C1—C2	1.377 (2)	C25—C26	1.406 (2)
C1—C6	1.394 (3)	C26—C27	1.391 (3)
C2—C3	1.391 (3)	C26—H26	0.9500
C2—H2	0.9500	C27—C28	1.388 (3)
C3—C4	1.374 (3)	C27—H27	0.9500
C3—H3	0.9500	C28—C29	1.384 (3)
C4—C5	1.387 (3)	C28—H28	0.9500
C4—H4	0.9500	C29—C30	1.388 (3)
C5—C6	1.381 (3)	C29—H29	0.9500
C5—H5	0.9500	C30—H30	0.9500
C6—H6	0.9500	C31—C32	1.402 (2)
C7—C12	1.381 (3)	C31—C36	1.406 (2)
C7—C8	1.388 (3)	C32—C33	1.392 (3)
C8—C9	1.389 (3)	C32—H32	0.9500
C8—H8	0.9500	C33—C34	1.381 (3)
C9—C10	1.385 (3)	C33—H33	0.9500
C9—H9	0.9500	C34—C35	1.378 (3)
C10—C11	1.385 (3)	C34—H34	0.9500
C10—H10	0.9500	C35—C36	1.394 (3)
C11—C12	1.397 (3)	C35—H35	0.9500
C11—H11	0.9500	C36—H36	0.9500
C12—H12	0.9500	C37—C42	1.402 (3)
C13—C18	1.384 (3)	C37—C38	1.404 (3)
C13—C14	1.393 (3)	C38—C39	1.403 (3)
C14—C15	1.384 (3)	C38—H38	0.9500
C14—H14	0.9500	C39—C40	1.375 (3)
C15—C16	1.380 (3)	C39—H39	0.9500
C15—H15	0.9500	C40—C41	1.382 (3)
C16—C17	1.379 (3)	C40—H40	0.9500
C16—H16	0.9500	C41—C42	1.394 (3)
C17—C18	1.392 (3)	C41—H41	0.9500
C17—H17	0.9500	C42—H42	0.9500
C18—H18	0.9500	C43—C44	1.402 (2)
C19—C20	1.381 (2)	C43—C48	1.407 (2)
C19—C24	1.392 (2)	C44—C45	1.396 (2)
C20—C21	1.394 (3)	C44—H44	0.9500
C20—H20	0.9500	C45—C46	1.385 (3)
C21—C22	1.381 (3)	C45—H45	0.9500
C21—H21	0.9500	C46—C47	1.392 (3)
C22—C23	1.384 (3)	C46—H46	0.9500
C22—H22	0.9500	C47—C48	1.397 (2)
C23—C24	1.388 (3)	C47—H47	0.9500
C23—H23	0.9500	C48—H48	0.9500

N1—Se1—C1	98.58 (7)	C25—B1—C31	111.14 (14)
N1—Se1—C7	98.26 (7)	C25—B1—C43	110.92 (13)
C1—Se1—C7	97.16 (7)	C31—B1—C43	106.23 (13)
N1—S1—C13	101.27 (8)	C25—B1—C37	104.14 (13)
N1—S1—C19	102.34 (8)	C31—B1—C37	113.60 (14)
C13—S1—C19	98.82 (8)	C43—B1—C37	110.91 (13)
S1—N1—Se1	109.71 (8)	C30—C25—C26	115.34 (16)
C2—C1—C6	122.29 (17)	C30—C25—B1	124.65 (15)
C2—C1—Se1	117.29 (14)	C26—C25—B1	119.51 (15)
C6—C1—Se1	120.38 (14)	C27—C26—C25	122.76 (18)
C1—C2—C3	118.39 (18)	C27—C26—H26	118.6
C1—C2—H2	120.8	C25—C26—H26	118.6
C3—C2—H2	120.8	C28—C27—C26	119.71 (19)
C4—C3—C2	120.23 (19)	C28—C27—H27	120.1
C4—C3—H3	119.9	C26—C27—H27	120.1
C2—C3—H3	119.9	C29—C28—C27	119.39 (19)
C3—C4—C5	120.65 (19)	C29—C28—H28	120.3
C3—C4—H4	119.7	C27—C28—H28	120.3
C5—C4—H4	119.7	C28—C29—C30	120.1 (2)
C6—C5—C4	120.30 (19)	C28—C29—H29	119.9
C6—C5—H5	119.8	C30—C29—H29	119.9
C4—C5—H5	119.8	C29—C30—C25	122.63 (19)
C5—C6—C1	118.10 (19)	C29—C30—H30	118.7
C5—C6—H6	120.9	C25—C30—H30	118.7
C1—C6—H6	120.9	C32—C31—C36	114.44 (16)
C12—C7—C8	121.98 (17)	C32—C31—B1	123.67 (16)
C12—C7—Se1	119.49 (13)	C36—C31—B1	121.88 (16)
C8—C7—Se1	118.38 (14)	C33—C32—C31	122.98 (19)
C7—C8—C9	118.76 (18)	C33—C32—H32	118.5
C7—C8—H8	120.6	C31—C32—H32	118.5
C9—C8—H8	120.6	C34—C33—C32	120.30 (19)
C10—C9—C8	120.21 (18)	C34—C33—H33	119.9
C10—C9—H9	119.9	C32—C33—H33	119.9
C8—C9—H9	119.9	C35—C34—C33	118.96 (18)
C9—C10—C11	120.28 (18)	C35—C34—H34	120.5
C9—C10—H10	119.9	C33—C34—H34	120.5
C11—C10—H10	119.9	C34—C35—C36	120.04 (19)
C10—C11—C12	120.29 (19)	C34—C35—H35	120.0
C10—C11—H11	119.9	C36—C35—H35	120.0
C12—C11—H11	119.9	C35—C36—C31	123.07 (18)
C7—C12—C11	118.48 (18)	C35—C36—H36	118.5
C7—C12—H12	120.8	C31—C36—H36	118.5
C11—C12—H12	120.8	C42—C37—C38	114.59 (17)
C18—C13—C14	121.34 (18)	C42—C37—B1	118.69 (15)
C18—C13—S1	116.59 (15)	C38—C37—B1	126.71 (16)
C14—C13—S1	121.95 (14)	C39—C38—C37	122.57 (19)
C15—C14—C13	118.67 (19)	C39—C38—H38	118.7
C15—C14—H14	120.7	C37—C38—H38	118.7
C13—C14—H14	120.7	C40—C39—C38	120.8 (2)
C16—C15—C14	120.8 (2)	C40—C39—H39	119.6
C16—C15—H15	119.6	C38—C39—H39	119.6
C14—C15—H15	119.6	C39—C40—C41	118.43 (19)
C17—C16—C15	119.9 (2)	C39—C40—H40	120.8
C17—C16—H16	120.0	C41—C40—H40	120.8
C15—C16—H16	120.0	C40—C41—C42	120.50 (19)
C16—C17—C18	120.7 (2)	C40—C41—H41	119.7
C16—C17—H17	119.7	C42—C41—H41	119.7
C18—C17—H17	119.7	C41—C42—C37	123.12 (19)
C13—C18—C17	118.6 (2)	C41—C42—H42	118.4
C13—C18—H18	120.7	C37—C42—H42	118.4
C17—C18—H18	120.7	C44—C43—C48	115.18 (16)
C20—C19—C24	121.50 (17)	C44—C43—B1	120.25 (15)
C20—C19—S1	121.21 (13)	C48—C43—B1	124.56 (15)
C24—C19—S1	117.28 (13)	C45—C44—C43	122.92 (18)
C19—C20—C21	118.86 (17)	C45—C44—H44	118.5
C19—C20—H20	120.6	C43—C44—H44	118.5
C21—C20—H20	120.6	C46—C45—C44	120.13 (18)
C22—C21—C20	120.26 (18)	C46—C45—H45	119.9
C22—C21—H21	119.9	C44—C45—H45	119.9
C20—C21—H21	119.9	C45—C46—C47	119.05 (17)
C21—C22—C23	120.29 (18)	C45—C46—H46	120.5
C21—C22—H22	119.9	C47—C46—H46	120.5
C23—C22—H22	119.9	C46—C47—C48	119.91 (18)
C22—C23—C24	120.36 (17)	C46—C47—H47	120.0
C22—C23—H23	119.8	C48—C47—H47	120.0
C24—C23—H23	119.8	C47—C48—C43	122.79 (18)
C23—C24—C19	118.71 (17)	C47—C48—H48	118.6
C23—C24—H24	120.6	C43—C48—H48	118.6
C19—C24—H24	120.6

C13—S1—N1—Se1	−131.24 (9)	C37—B1—C25—C30	106.80 (19)
C19—S1—N1—Se1	127.02 (9)	C31—B1—C25—C26	58.0 (2)
C1—Se1—N1—S1	−135.99 (9)	C43—B1—C25—C26	175.90 (15)
C7—Se1—N1—S1	125.42 (9)	C37—B1—C25—C26	−64.74 (19)
N1—Se1—C1—C2	131.25 (14)	C30—C25—C26—C27	−0.6 (3)
C7—Se1—C1—C2	−129.22 (14)	B1—C25—C26—C27	171.66 (17)
N1—Se1—C1—C6	−46.91 (16)	C25—C26—C27—C28	−0.9 (3)
C7—Se1—C1—C6	52.61 (16)	C26—C27—C28—C29	1.3 (3)
C6—C1—C2—C3	1.0 (3)	C27—C28—C29—C30	0.0 (4)
Se1—C1—C2—C3	−177.11 (14)	C28—C29—C30—C25	−1.6 (4)
C1—C2—C3—C4	0.5 (3)	C26—C25—C30—C29	1.9 (3)
C2—C3—C4—C5	−0.8 (3)	B1—C25—C30—C29	−169.9 (2)
C3—C4—C5—C6	−0.3 (3)	C25—B1—C31—C32	11.6 (2)
C4—C5—C6—C1	1.7 (3)	C43—B1—C31—C32	−109.18 (17)
C2—C1—C6—C5	−2.1 (3)	C37—B1—C31—C32	128.62 (17)
Se1—C1—C6—C5	175.96 (15)	C25—B1—C31—C36	−169.43 (15)
N1—Se1—C7—C12	−29.99 (16)	C43—B1—C31—C36	69.82 (19)
C1—Se1—C7—C12	−129.79 (15)	C37—B1—C31—C36	−52.4 (2)
N1—Se1—C7—C8	154.48 (15)	C36—C31—C32—C33	3.6 (3)
C1—Se1—C7—C8	54.68 (16)	B1—C31—C32—C33	−177.32 (16)
C12—C7—C8—C9	−0.2 (3)	C31—C32—C33—C34	0.3 (3)
Se1—C7—C8—C9	175.23 (15)	C32—C33—C34—C35	−3.0 (3)
C7—C8—C9—C10	0.3 (3)	C33—C34—C35—C36	1.6 (3)
C8—C9—C10—C11	−0.5 (3)	C34—C35—C36—C31	2.6 (3)
C9—C10—C11—C12	0.7 (3)	C32—C31—C36—C35	−5.0 (3)
C8—C7—C12—C11	0.3 (3)	B1—C31—C36—C35	175.88 (17)
Se1—C7—C12—C11	−175.03 (14)	C25—B1—C37—C42	−43.5 (2)
C10—C11—C12—C7	−0.6 (3)	C31—B1—C37—C42	−164.59 (15)
N1—S1—C13—C18	112.98 (16)	C43—B1—C37—C42	75.84 (19)
C19—S1—C13—C18	−142.46 (16)	C25—B1—C37—C38	135.44 (18)
N1—S1—C13—C14	−63.08 (17)	C31—B1—C37—C38	14.4 (2)
C19—S1—C13—C14	41.48 (17)	C43—B1—C37—C38	−105.19 (19)
C18—C13—C14—C15	0.2 (3)	C42—C37—C38—C39	−1.6 (3)
S1—C13—C14—C15	176.08 (16)	B1—C37—C38—C39	179.38 (18)
C13—C14—C15—C16	−0.3 (3)	C37—C38—C39—C40	1.4 (3)
C14—C15—C16—C17	0.0 (4)	C38—C39—C40—C41	−0.1 (3)
C15—C16—C17—C18	0.5 (4)	C39—C40—C41—C42	−0.8 (3)
C14—C13—C18—C17	0.3 (3)	C40—C41—C42—C37	0.5 (3)
S1—C13—C18—C17	−175.81 (17)	C38—C37—C42—C41	0.7 (3)
C16—C17—C18—C13	−0.6 (3)	B1—C37—C42—C41	179.77 (17)
N1—S1—C19—C20	−2.88 (16)	C25—B1—C43—C44	−64.4 (2)
C13—S1—C19—C20	−106.55 (16)	C31—B1—C43—C44	56.47 (19)
N1—S1—C19—C24	178.16 (14)	C37—B1—C43—C44	−179.64 (15)
C13—S1—C19—C24	74.48 (15)	C25—B1—C43—C48	116.55 (18)
C24—C19—C20—C21	−1.7 (3)	C31—B1—C43—C48	−122.55 (17)
S1—C19—C20—C21	179.35 (14)	C37—B1—C43—C48	1.3 (2)
C19—C20—C21—C22	1.7 (3)	C48—C43—C44—C45	−0.1 (3)
C20—C21—C22—C23	−0.7 (3)	B1—C43—C44—C45	−179.21 (16)
C21—C22—C23—C24	−0.5 (3)	C43—C44—C45—C46	−0.5 (3)
C22—C23—C24—C19	0.5 (3)	C44—C45—C46—C47	1.2 (3)
C20—C19—C24—C23	0.6 (3)	C45—C46—C47—C48	−1.3 (3)
S1—C19—C24—C23	179.59 (14)	C46—C47—C48—C43	0.7 (3)
C31—B1—C25—C30	−130.51 (18)	C44—C43—C48—C47	0.0 (3)
C43—B1—C25—C30	−12.6 (2)	B1—C43—C48—C47	179.06 (16)

Experimental details

Crystal data
Chemical formula	C₂₄H₂₀NSSe⁺·C₂₄H₂₀B⁻
M_r	752.64
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	12.2627 (11), 27.860 (2), 12.2402 (11)
β (°)	114.438 (2)
V (Å³)	3807.1 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.08
Crystal size (mm)	0.67 × 0.26 × 0.24

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.532, 0.782
No. of measured, independent and observed [I > 2σ(I)] reflections	32563, 9135, 7611
R_int	0.078
(sin θ/λ)_max (Å⁻¹)	0.680

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.116, 1.02
No. of reflections	9135
No. of parameters	470
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.93, −0.94

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXTL (Sheldrick, 2000), SHELXTL and local programs.

Selected geometric parameters (Å, º) top

Se1—N1	1.8045 (14)	S1—N1	1.6735 (15)
Se1—C1	1.9066 (18)	S1—C13	1.8088 (18)
Se1—C7	1.9231 (18)	S1—C19	1.8249 (17)

S1—N1—Se1	109.71 (8)

Acknowledgements

The authors acknowledge the EPSRC for PDRA support (LMG and SMA) and use of the EPSRC Chemical Database Service at Daresbury Laboratory (Fletcher et al., 1996).

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