(4-Nitrophenylsulfanylmethyl)triphenylstannane and (4-nitrophenylsulfonylmethyl)triphenylstannane: R22(X) rings (X is 10, 18 or 24) and C-H...π interactions

Article abstract of DOI:10.1107/S0108270102010375

In the crystal structures of (4-nitrophenylsulfanylmethyl)triphenylstannane, [Sn(C₆H₅)₃(C₇H₆ NO₂S)]. (I), and (4-nitrophenylsulfonylmethyl)triphenylstannane. [Sn(C₆H₅)₃(C₇H₆ NO₄S)], (II), the molecules are linked by paired C-H...O hydrogen bonds into centrosymmetric dimers which combine to form sheets. In (I), two such dimers form to give R₂²(10) and R₂²(24) rings. In (II), similar dimers form, here with R₂²(10) and R₂²(18) rings, but with an additional dimer due to the presence of the sulfone group, giving R₂²(10) rings. In both structures, C-H...π interactions lead to a doubling of the width of the sheets.

Full text of DOI:10.1107/S0108270102010375

metal-organic compounds
Acta Crystallographica Section C
Crystal Structure
Communications
Molecules of (I) are linked by two different CÐHÁ Á ÁO
hydrogen bonds (Table 1) into centrosymmetric dimers, where
nitro O atoms act as acceptors. The phenyl atom C5 at (x, y, z)
ISSN 0108-2701
acts as a hydrogen-bond donor to nitro atom O1 at (3
2
x,
y, z), thus forming a dimer characterized by an R22(10)
motif with an inversion centre at (32,1,0). Similarly, atom C36 at
(x, y, z) acts as a donor to nitro atom O2 at (2 x, 1 y, z),
giving an R22(24) ring with an inversion centre at (1,12,0). These
two dimers combine to form a sheet which propagates along
[110] (Fig. 3). In addition, the phenyl rings of neighbouring
molecules are weakly linked by CÐHÁ Á Áꢀ interactions. One of
these interactions extends the sheet along the z direction;
atom C15 at (x, y, z) donates to the C21±C26 phenyl ring at
(4-Nitrophenylsulfanylmethyl)tri-
phenylstannane and (4-nitrophenyl-
sulfonylmethyl)triphenylstannane:
R22(X) rings (X is 10, 18 or 24) and
CÐHÁ Á Áp interactions
Ê
(1 x, 2 y, 1 z), with a distance of 3.661 (3) A between
Janet M. S. Skakle,a* James L. Wardellb and
Solange M. S. V. Wardellc
atom C15 and the ring centroid. Such dimers are shown in
Fig. 4, and they have the effect of doubling the width of the
sheets shown in Fig. 3.
aDepartment of Chemistry, University of Aberdeen, Meston Walk, Aberdeen
b
Â
Ã
Â
AB24 3UE, Scotland, Departamento de Quõmica Inorganica, Instituto de Quõmica,
Universidade Federal do Rio de Janeiro, 21945-970 Rio de Janeiro RJ, Brazil, and
c
Â
Ã
Â
Departamento de Quõmica Organica, Instituto de Quõmica, Universidade Federal
Â
Fluminense, 24020-150 Niteroi, Rio de Janeiro, Brazil
Correspondence e-mail: j.skakle@abdn.ac.uk
Received 27 May 2002
Accepted 10 June 2002
Online 29 June 2002
In the crystal structures of (4-nitrophenylsulfanylmethyl)tri-
phenylstannane, [Sn(C6H5)3(C7H6NO2S)], (I), and (4-nitro-
phenylsulfonylmethyl)triphenylstannane, [Sn(C6H5)3(C7H6N-
O4S)], (II), the molecules are linked by paired CÐHÁ Á ÁO
hydrogen bonds into centrosymmetric dimers which combine
to form sheets. In (I), two such dimers form to give R22(10) and
R22(24) rings. In (II), similar dimers form, here with R22(10) and
R22(18) rings, but with an additional dimer due to the presence
of the sulfone group, giving R22(10) rings. In both structures,
CÐHÁ Á Áꢀ interactions lead to a doubling of the width of the
sheets.
Figure 1
A view of the molecule of (I) showing the atom-labelling scheme.
Displacement ellipsoids are drawn at the 50% probability level and H
atoms have been omitted for clarity.
Comment
The intermolecular non-bonded interactions in a number of
nitro, sulfanyl and sulfonyl aromatic derivatives have been
investigated in the solid state (Kelly et al., 2002; Cannon et al.,
2000, 2001; Glidewell et al., 2001; Wardell et al., 2000a,b).
Continuing our studies, the structures of (4-nitrophenyl-
sulfanylmethyl)triphenylstannane, (I), and (4-nitrophenyl-
sulfonylmethyl)triphenylstannane, (II), have now been
investigated and the results are presented here.
Figure 2
A view of the molecule of (II) showing the atom-labelling scheme.
Displacement ellipsoids are drawn at the 50% probability level and H
atoms have been omitted for clarity.
Both (I) (Fig. 1) and (II) (Fig. 2) crystallize in the triclinic
space group P1 and form sheets via similar soft interactions.
Acta Cryst. (2002). C58, m413±m417
DOI: 10.1107/S0108270102010375
# 2002 International Union of Crystallography m413

metal-organic compounds
Figure 3
Part of the crystal structure of (I) showing dimers containing R22(10) and
R22(24) rings [symmetry codes: (i) 3 x, 2 y, z; (ii) 2 x, 1 y, z].
Figure 5
Part of the crystal structure of (II) showing dimers containing R22(10) and
R22(18) rings [symmetry codes: (i) x, 1 y, z; (ii) x, 2 y, z].
Molecules of (II) are also linked via intermolecular CÐ
HÁ Á ÁO interactions. In this case, the sulfone group leads to one
further bond (Table 2). Considering the nitro acceptor inter-
actions ®rst, phenyl atom C5 at (x, y, z) acts as a hydrogen-
bond donor to nitro atom O1 at ( x, 1 y, z), to give an
R22(10) motif centred at (0,12,0). Similarly, atom C7 at (x, y, z)
acts as the donor, whereas in (II), the CH2 group is the donor,
effectively contracting the size of the R22(X) ring.
An extra hydrogen bond occurs due to the presence of the
sulfone group. Phenyl atom C2 at (x, y, z) acts as a hydrogen-
bond donor to sulfone atom O4 at (1 x, 2 y, z), forming
an R22(10) motif with an inversion centre at (12,1,0). These three
dimers thus combine to form a sheet which propagates along
[110] (Fig. 6), as in the structure of (I).
donates to the nitro atom O2 at ( x, 2
y, z), giving an
R22(18) ring centred at (0,1,0), forming a chain along [010] (Fig.
5). Thus, the effect of the sulfone group is to alter the local
conformation and thus the CÐHÁ Á ÁO bonding to the second
nitro O atom. In (I), a phenyl H atom from the Ph3Sn group
Figure 4
The dimers formed from CÐHÁ Á Áꢀ interactions in (I) via the symmetry
Figure 6
translation (1 x, 2 y, 1 z).
The chains formed by CÐHÁ Á ÁO interactions in (II).
ꢀ
m414 Janet M. S. Skakle et al.
[Sn(C6H5)3(C7H6NO2S)] and [Sn(C6H5)3(C7H6NO4S)]
Acta Cryst. (2002). C58, m413±m417

metal-organic compounds
As with (I), the phenyl groups in (II) form CÐHÁ Á Áꢀ
interactions with neighbouring molecules within the sheet. In
addition, atom C33 at (x, y, z) donates a hydrogen bond to the
C21±C26 phenyl ring at (2 x, 1 y, 1 z), with a distance of
CHClCH2SC6H3NO2-2-Me-4 (PAGHEK; Howie et al., 1992),
Ph3SnCH(SCN)CH2SC6H4NO2-2 (PAGHIO; Howie et al.,
t
1992), (cyclohexyl)3SnCH2SC6H4 Bu-4 (JERMIC; Cox et al.,
1990), Ph3Ge(CH2)SO2C6H5 (NOJXEP; Wardell & Cox,
1996), Ph3SnC(SMe) CHC6H5 (GODLOA and GODLUG;
Bruhn et al., 1999), Ph3SnC(SCH2Ph)CHCHC(SCH2Ph)SnPh3
(POMXUK; Block et al., 1994) and Ph3SnCH2CH2SC6H4Me-4
(ZUWQIR; Cox et al., 1995).
Of these, the ®rst four (GESYIM, ZIKHOQ, YEZVEE and
YEZVII) have CÐHÁ Á ÁO bonds which can be considered in
relation to (I) and (II). The latter four compounds
(GODLOA, GODLUG, POMXUK and ZUWQIR) display
CÐHÁ Á ÁS interactions, while the rest do not form hydrogen
bonds, as detected by PLATON (Spek, 2002).
Ê
3.361 A between the H atom and the centroid (Fig. 7), which,
as in (I), has the effect of doubling the width of the sheet.
The Sn centre in (I) is four-coordinate; the bond angles, in
the range 106.27 (10)±114.64 (8)ꢁ, indicate a slightly distorted
tetrahedral geometry. The SnÐC bond lengths are in the
expected region and fall in a narrow range, 2.138 (2)±
Ê
2.172 (2) A. The bond lengths in (II) show a greater range,
with those involving the phenyl groups being between
Ê
2.1275 (15) and 2.1371 (15) A, and the SnÐCalkyl length being
Ê
longer than these, at 2.1815 (14) A. The bond angles
subtended at Sn in (II) range from 101.15 (5) to 111.76 (6)ꢁ,
again indicative of a slightly distorted tetrahedral geometry.
Ph3GeCH2SO2C6H5 (GESYIM), a Ge analogue to (II),
forms hydrogen bonds via the CH2 group as donor to a sulfone
O atom, thus forming simple C(4) chains along [001]. No rings
are formed. Ph3Sn(CH2)2CH(SC6H4NO2-2)CH2Cl (ZIK-
HOQ), in which the nitro group is ortho to S, again has CH2 as
the donor to one nitro O atom as acceptor, forming R22(16)
dimers. The other H atom of the CH2 group donates to the
other nitro O atom, forming a chain of dimers along [001].
Ph3Sn(CH2)2SO2C6H4Me-4 (YEZVEE) again donates a
hydrogen bond via the CH2 group adjacent to S to a sulfone O
atom; in addition, a phenyl H atom acts as a donor to the same
O atom, forming R23(13) groups which link to give C(8) chains
along [100]. In the related compound Ph3Sn(CH2)4-
SO2C6H4Me-4 (YEZVII), similar hydrogen bonding occurs,
although here via the third CH2 group from S, to give an
R23(16) motif, linking to give C(12) chains along [010]. Both
motifs are enlarged by the extra CH2 groups in the latter
compound.
Ê
The closest SnÁ Á ÁOsulfone separation is SnÁ Á ÁO4 3.5906 (12) A,
Ê
a little within the sum of the van der Waals radii of 3.70 A.
A number of related triphenyl±Sn and ±Ge structures have
been reported, along with one related iododiphenyltin
compound (CSD database, Release 5.23; Allen & Kennard,
1993). These are Ph3GeCH2SO2C6H5 (CSD refcode GESYIM;
Howie & Wardell, 1997), Ph3Sn(CH2)2CH(SC6H4NO2-2)CH2-
Cl (ZIKHOQ; Aupers & Wardell, 1995), Ph3Sn(CH2)2SO2-
C6H4Me-4 [(III), n = 2, YEZVEE; Cox & Wardell, 1994],
Ph3Sn(CH2)4SO2C6H4Me-4 [(III), n = 4, YEZVII; Cox &
Wardell, 1994], Ph3Sn(CH2)3SO2C6H4Me-4 [(III), n = 3,
ZAVHIN; Howie
&
SO2C6H4Me-4 (ZAVHOT; Howie & Wardell, 1994), Ph3Sn-
Wardell, 1994], IPh2Sn(CH2)3-
The products of the reactions of !-sulfanylalkylstannanes,
R3Sn(CH2)nSR0, with oxidants depend greatly on n and on the
oxidant. For example, (II) was obtained by H2O2 oxidation of
(I), whereas the reaction of the related compound
Ph3Sn(CH2)nSC6H4Me-4 [(IV), n = 1] with NaIO4 led to
cleavage of the molecule with formation of Ph3SnCH2I and
4-MeC6H4SO3H (Taylor & Wardell, 1976; see also Peterson,
1971). The use of 3-ClC6H4CO3H with (IV), with n = 1, also
resulted in cleavage (Wardell, unpublished observation). In
contrast, oxidations of (IV) with n = 3 or 4 proceeded readily
to the sulfones (III) with n = 3 or 4, or the corresponding
sulfoxides, depending on the molar ratios of the reagents
(Wardell & Wigzell, 1983). Particularly sensitive to oxidants is
(IV) with n = 2. The reaction of (IV) with n = 2 with either
NaIO4 or 3-ClC6H4CO3H led to loss of ethylene (Wardell &
Wigzell, 1983). Compound (IV) with n = 2 was, however,
obtained by the addition of Ph3SnH to H2C CH-
SO2C6H4Me-4 (Wardell & Wigzell, 1983). The contrast
between the Ge and Sn compounds is clear from the reactions
of Ph3MCH2SR0 (M is Ge or Sn) with 3-ClC6H4CO3H or Br2.
The Br2±R3SnCH2SR0 reactions invariably result in SnÐC
bond cleavage, while the Ge compounds can be oxidized to
Ph3GeCH2SOmR (m = 1 or 2) by either Br2 in MeOH or
3-ClC6H4CO3H (Taylor & Wardell, 1976; Wardell & Cox,
1996).
Figure 7
The dimers formed by CÐHÁ Á Áꢀ interactions in (II) via the symmetry
translation (1 x, 2 y, 1 z).
ꢀ
Acta Cryst. (2002). C58, m413±m417
Janet M. S. Skakle et al.
[Sn(C6H5)3(C7H6NO2S)] and [Sn(C6H5)3(C7H6NO4S)] m415

metal-organic compounds
Compound (II)
Experimental
Compound (I) was prepared from Ph3SnCH2I, HSC6H4NO2 and
NaOEt (2 mmol scale) in EtOH (20 ml). After re¯uxing for 2 h, the
mixture was cooled, all volatiles removed and the residue recrys-
tallized from EtOH (m.p. 416±418 K). Analysis found: C 58.4, H 5.5,
S 6.3, N 3.1%; calculated for C24H21NO2SSn: C 58.0, H 4.1, S 6.2,
N 2.7%. Spectroscopic analysis, 1H NMR (250 Hz, CDCl3, ꢁ, p.p.m.):
2.88 [s, 2H, J(119,117Sn 1H) = 48.8 Hz, CH2], 7.41 (m, 11H, m-H + p-H
of Ph3Sn + 2H from C6H4), 7.60 [m, 6H, J(119,117Sn 1H) ꢂ 57 Hz, o-H
of Ph3Sn], 8.10 (d, 2H, J = 8.8 Hz, C6H4); 13C NMR (63.3 Hz, CDCl3,
ꢁ, p.p.m.): 5.2 (CH2), 123.8 (C3), 124.6 (C2), 128.9 (m-C of Ph3Sn),
129.7 (p-C of Ph3Sn), 136.7 (i-C of Ph3Sn), 137.0 (o-C of Ph3Sn), 144.0
(C1), 152.7 (C4); 119Sn NMR (93.3 Hz, CD2Cl2, ꢁ, p.p.m.): 118; IR
(KBr, cm 1): 1578 and 1339 (NO2); Raman (cm 1): 1587, 1331.
Compound (II) was obtained by H2O2 oxidation (30% solution in
water) of (I) in a mixed H2O±CH2Cl2 medium. After stirring the
reaction mixture overnight at room temperature, all volatiles were
removed and the residue was recrystallized from EtOH (m.p. 472±
Crystal data
[Sn(C6H5)3(C7H6NO4S)]
Mr = 550.18
Triclinic, P1
a = 6.8715 (4) A
Ê
b = 9.9680 (5) A
Z = 2
Dx = 1.606 Mg m
Mo Kꢂ radiation
3
Ê
Cell parameters from 10 598
re¯ections
ꢅ = 2.3±28.9ꢁ
ꢆ = 1.25 mm
T = 120 (2) K
Ê
c = 17.6403 (10) A
1
ꢂ = 81.0264 (19)ꢁ
ꢃ = 89.4798 (19)ꢁ
ꢄ = 72.5146 (17)ꢁ
Block, colourless
0.5 Â 0.3 Â 0.3 mm
3
Ê
V = 1137.42 (11) A
Data collection
Bruker SMART CCD area-detector
diffractometer
' and ! scans
Absorption correction: multi-scan
(SADABS; Sheldrick, 1997)
Tmin = 0.674, Tmax = 0.688
10 598 measured re¯ections
5261 independent re¯ections
5061 re¯ections with I > 2ꢇ(I)
Rint = 0.011
ꢅmax = 28.9ꢁ
h = 9 ! 8
k = 13 ! 13
l = 23 ! 23
1
475 K). Spectroscopic analysis, H NMR (250 Hz, CDCl3, ꢁ, p.p.m.):
3.44 [s, 2H, J(119,117Sn 1H) = 41.2 Hz, CH2], 7.43 (m, 9H, p-H + m-H
of Ph3Sn), 7.63 [m, 6H, J(119,117Sn 1H) ꢂ 60 Hz, o-H of Ph3Sn], 8.06
(d, 2H, J = 8.6 Hz, C6H4), 8.28 (m, 2H, J = 8.6 Hz, C6H4); 13C NMR
(63.3 Hz, CDCl3, ꢁ, p.p.m.): 44.5 (CH2), 124.4 (C3), 128.2 (C2), 129.0
(m-C of Ph3Sn), 129.9 (p-C of Ph3Sn), 135.8 (i-C of Ph3Sn), 137.0 (o-C
of Ph3Sn), C4 and C1 not observed; IR (Nujol mull, cm 1): 1527 and
1304 (NO2), 1377 and 1145 (SO2).
Re®nement
Re®nement on F2
R[F2 > 2ꢇ(F2)] = 0.018
wR(F2) = 0.046
S = 1.10
5261 re¯ections
w = 1/[ꢇ2(Fo2) + (0.0246P)2
+ 0.5422P]
where P = (Fo2 + 2Fc2)/3
(Á/ꢇ)max = 0.002
3
Ê
Áꢈmax = 0.38 e A
3
Ê
0.61 e A
289 parameters
H-atom parameters constrained
Áꢈmin
=
Compound (I)
Table 2
Hydrogen-bonding geometry (A, ) for (II).
ꢁ
Ê
Crystal data
[Sn(C6H5)3(C7H6NO2S)]
Mr = 518.18
Triclinic, P1
Z = 2
Dx = 1.555 Mg m
Mo Kꢂ radiation
DÐHÁ Á ÁA
DÐH
HÁ Á ÁA
DÁ Á ÁA
DÐHÁ Á ÁA
3
C2ÐH2Á Á ÁO4i
C5ÐH5Á Á ÁO1ii
C7ÐH7BÁ Á ÁO2iii
0.95
0.95
0.99
2.58
2.48
2.36
3.2753 (19)
3.204 (2)
3.3163 (19)
131
133
161
Ê
a = 6.6442 (1) A
Cell parameters from 12 524
re¯ections
Ê
b = 10.3070 (2) A
c = 17.2597 (4) A
ꢅ = 2.9±27.5ꢁ
ꢆ = 1.27 mm
T = 150 (2) K
Ê
1
Symmetry codes: (i) 1 x; 2 y; z; (ii) x; 1 y; z; (iii) x; 2 y; z.
ꢂ = 100.3385 (8)ꢁ
ꢃ = 98.6403 (9)ꢁ
ꢄ = 103.6969 (16)ꢁ
Needle, yellow
0.40 Â 0.10 Â 0.03 mm
3
Ê
V = 1106.51 (4) A
Data collection
Structure (I) was solved using Patterson methods (SHELXS86;
Sheldrick, 1990) in P1, and then the coordinates were converted to
P1. All H atoms were placed in geometrically calculated positions,
Ê
with CÐH distances of 0.95 (phenyl) and 0.99 A (CH2), and re®ned
using a riding model.
Nonius KappaCCD area-detector
diffractometer
' and ! scans
Absorption correction: empirical
(SORTAV; Blessing, 1995, 1997)
Tmin = 0.817, Tmax = 0.992
16 551 measured re¯ections
5030 independent re¯ections
4460 re¯ections with I > 2ꢇ(I)
Rint = 0.052
ꢅ
max = 27.5ꢁ
h = 8 ! 8
For compound (I), data collection: DENZO (Otwinowski &
Minor, 1997) and COLLECT (Hooft, 1998); cell re®nement: DENZO
and COLLECT; data reduction: DENZO and COLLECT;
program(s) used to solve structure: SHELXS86. For compound (II),
data collection: SMART (Bruker, 1999); cell re®nement: SAINT
(Bruker, 1999); data reduction: SAINT; program(s) used to solve
structure: SHELXS97 (Sheldrick, 1990). For both compounds,
program(s) used to re®ne structure: SHELXL97 (Sheldrick, 1997);
molecular graphics: ORTEX in OSCAIL (McArdle, 1994, 2000) and
ORTEP-3 for Windows (Farrugia, 1997); software used to prepare
material for publication: SHELXL97.
k = 13 ! 13
l = 22 ! 22
Re®nement
Re®nement on F2
R[F2 > 2ꢇ(F2)] = 0.032
wR(F2) = 0.079
S = 1.06
5030 re¯ections
271 parameters
H-atom parameters constrained
w = 1/[ꢇ2(Fo2) + (0.0434P)2]
where P = (Fo2 + 2Fc2)/3
(Á/ꢇ)max = 0.001
3
Ê
Áꢈmax = 0.82 e A
3
Ê
1.39 e A
Áꢈmin
=
Table 1
Hydrogen-bonding geometry (A, ) for (I).
ꢁ
Ê
The authors thank the EPSRC X-ray Crystallographic
Service, University of Southampton, England, for the collec-
tion of data, and acknowledge the use of the EPSRC Chemical
Database Service at Daresbury (Fletcher et al., 1996). JLWand
SMSVW thank CNPq for support.
DÐHÁ Á ÁA
DÐH
HÁ Á ÁA
DÁ Á ÁA
DÐHÁ Á ÁA
C5ÐH5Á Á ÁO1i
0.95
0.95
2.56
2.57
3.151 (3)
3.439 (3)
121
152
C36ÐH36Á Á ÁO2ii
Symmetry codes: (i) 3 x; 2 y; z; (ii) 2 x; 1 y; z.
ꢀ
m416 Janet M. S. Skakle et al.
[Sn(C6H5)3(C7H6NO2S)] and [Sn(C6H5)3(C7H6NO4S)]
Acta Cryst. (2002). C58, m413±m417

metal-organic compounds
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