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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoSTRUCTURAL
CHEMISTRY
ISSN: 2053-2296
Volume 62| Part 7| July 2006| Pages o423-o425
doi:10.1107/S0108270106019408

4-Iodo-N,N-bis­(2-nitro­phenyl­sulfon­yl)aniline: a three-dimensional framework structure built from six independent C—H⋯O hydrogen bonds

CROSSMARK_Color_square_no_text.svg
John N. Low,a Janet M. S. Skakle,a James L. Wardellb and Christopher Glidewellc*

aDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland, bInstituto de Química, Departamento de Química Inorgânica, Universidade Federal do Rio de Janeiro, CP 68563, 21945-970 Rio de Janeiro, RJ, Brazil, and cSchool of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland
*Correspondence e-mail: cg@st-andrews.ac.uk

(Received 23 May 2006; accepted 24 May 2006; online 23 June 2006)

In the title compound [systematic name: 4-iodo­phenyl­imino bis­(2-nitro­benzene­sulfinate)], C18H12IN3O8S2, where the mol­ecules do not exhibit even approximate local symmetry, the mol­ecules are linked into a complex three-dimensional structure by six independent C—H⋯O hydrogen bonds, which utilize O atoms in nitro and sulfonyl groups as the acceptors.

Comment

We report here the structure of 4-iodo-N,N-bis(2-nitro­phenyl­sulfon­yl)aniline, (I)[link] (Fig. 1[link]), where the supra­molecular aggregation proves to be markedly different from that in the isomeric compound 4-iodo-N,N-bis(3-nitro­phenyl­sulfon­yl)­aniline, (II)[link], which was reported recently as part of a wider study of inter­molecular inter­actions in iodo­nitro­arene­sulfon­amides (Kelly et al., 2002[Kelly, C. J., Skakle, J. M. S., Wardell, J. L., Wardell, S. M. S. V., Low, J. N. & Glidewell, C. (2002). Acta Cryst. B58, 94-108.]). In (II)[link], the mol­ecules lie across twofold rotation axes in the space group C2/c, and they are linked into sheets by a combination of a C—H⋯O=S hydrogen bond and a three-centre iodo–sulfonyl inter­action, but the nitro O atoms play no role in the inter­molecular aggregation.

In (I)[link], the mol­ecules have a planar coordination at atom N1. The mol­ecular conformation is defined by eight torsion angles (Table 1[link]), and these show that the mol­ecules do not exhibit even approximate rotational symmetry; in particular, the orientations of the nitrated aryl rings and the nitro groups are very different for the two independent 2-nitro­phenyl­sulfonyl units within the mol­ecule.

There are no iodo–nitro or iodo–sulfonyl inter­actions nor aromatic π–π stacking inter­actions in the structure of (I)[link]; instead, the mol­ecules are linked into a complex three-dimensional framework by a combination of six independent C—H⋯O hydrogen bonds (Table 2[link]). However, the formation of the structure of (I)[link] can be analysed in terms of three one-dimensional substructures.

[Scheme 1]

In the first substructure, which is built from the two shortest hydrogen bonds, atoms C13 and C14 in the mol­ecule at (x, y, z) act as donors, respectively, to atoms O21 and O22 in the mol­ecules at (x, y, 1 + z) and (1 − x, 1 − y, 2 − z), and propagation by translation and inversion of these two hydrogen bonds generates a chain of edge-fused rings running parallel to the [001] direction, with R22(18) rings (Bernstein et al., 1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]) centred at ([1\over2], [1\over2], n) (n = zero or integer) and R44(14) rings centred at ([1\over2], [1\over2], [1\over2] + n) (n = zero or integer) (Fig. 2[link]).

The second substructure depends solely on inversion operations. Atoms C2 and C15 in the mol­ecule at (x, y, z) act as hydrogen-bond donors, respectively, to nitro atoms O221 and O222 in the mol­ecule at (1 − x, 1 − y, 1 − z), so forming a centrosymmetric motif in which an R22(22) ring surrounds an R22(18) ring (Fig. 3[link]). At the same time, atom C26 at (x, y, z) acts as a hydrogen-bond donor to sulfonyl atom O11 in the mol­ecule at (−x, 1 − y, 1 − z), so forming a centrosymmetric R22(14) motif. Propagation by inversion of these three hydrogen bonds generates a chain of edge-fused rings running parallel to the [100] direction, with R22(18) and R22(22) rings centred at ([1\over2] + n, [1\over2], [1\over2]) (n = zero or integer) and R22(14) rings centred at (n, [1\over2], [1\over2]) (n = zero or integer) (Fig. 4[link]).

The combination of the [001] and [100] chains (Figs. 2[link] and 4[link]) generates a sheet lying parallel to (010) and occupying the domain [1\over4] < y < [3\over4]; a second sheet, related to the first by the action of the translational symmetry elements, occupies the domain −[1\over4] < y < [1\over4], and the action of the third and final one-dimensional substructure is to link adjacent (010) sheets. Atom C23 in the mol­ecule at (x, y, z), which forms part of the sheet in the domain [1\over4] < y < [3\over4], acts as a hydrogen-bond donor to sulfonyl atom O22 in the mol­ecule at (x, [{1\over 2}] − y, −[{1\over 2}] + z), which itself forms part of the sheet in the domain −[1\over4] < y < [1\over4]. Hence, propagation of this hydrogen bond produces a C(6) chain running parallel to the [010] direction and generated by the c-glide plane at y = [1\over4] (Fig. 5[link]), whose effect is to link adjacent (010) sheets, thereby forming a continuous three-dimensional framework structure.

The C—H⋯O hydrogen bonds in (I)[link] (Table 2[link]) utilize three of the four sulfonyl O atoms as acceptors, with atom O22 acting as a double acceptor; while both O atoms of one of the nitro groups are employed as hydrogen-bond acceptors, those in the other nitro group play no role in the supra­molecular aggregation. In almost all respects, therefore, the direction-specific inter­molecular inter­actions in isomers (I)[link] and (II)[link] are different, leading to markedly different supra­molecular structures.

[Figure 1]
Figure 1
A view of the mol­ecule of (I)[link], showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2]
Figure 2
A stereoview of part of the crystal structure of (I)[link], showing the formation of a hydrogen-bonded chain along [001] built from alternating R22(18) and R44(14) rings. For the sake of clarity, H atoms not involved in the motif shown have been omitted.
[Figure 3]
Figure 3
Part of the crystal structure of (I)[link], showing the formation of two concentric ring motifs. For the sake of clarity, H atoms not involved in the motifs shown have been omitted. Atoms marked with an asterisk (*) are at the symmetry position (1 − x, 1 − y, 1 − z).
[Figure 4]
Figure 4
A stereoview of part of the crystal structure of (I)[link], showing the formation of a hydrogen-bonded chain along [100] built from R22(18) and R22(22) rings alternating with R44(14) rings. For the sake of clarity, H atoms not involved in the motif shown have been omitted.
[Figure 5]
Figure 5
Part of the crystal structure of (I)[link], showing the formation of a C(6) hydrogen-bonded chain along [010], which links adjacent (010) sheets. For the sake of clarity, H atoms not involved in the motif shown have been omitted. Atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (x, [{1\over 2}] − y, −[{1\over 2}] + z) and (x, [{1\over 2}] − y, [{1\over 2}] + z), respectively.

Experimental

A solution of 2-nitro­phenyl­sulfonyl chloride (1.11 g, 5 mmol), 4-iodo­aniline (0.55 g 2.5 mmol) and triethyl­amine (2 ml) in 1,2-di­chloro­ethane (20 ml) was heated under reflux for 0.5 h; the mixture was then cooled and the solvent was removed under reduced pressure. The solid product was purified by column chromatography on alumina using ethyl acetate as the eluant and then recrystallized from ethanol [m.p. 494–495 K (decomposition)]. NMR (CDCl3): δ(H) 6.76 (d, 2H, J = 8.9 Hz) and 7.75 (d, J = 8.9 Hz) (C6H4I group), 7.63 (dd, 2H, J = 7.9 and 1.4 Hz), 7.74 (dt, 2H, J = 7.9 and 1.4 Hz), 7.79 (dt, 2H, J = 7.9 and 1.4 Hz), 8.22 (dd, 2H, J = 7.9 and 1.4 Hz) (C6H4NO2 groups); IR (KBr disk, cm−1): 1537, 1479, 1464, 1442, 1389, 1367, 1269, 1199, 1169, 1145, 1122, 1057, 1009, 958, 930, 900, 850, 807, 778, 740, 698, 653, 612, 586, 535, 414.

Crystal data

  • C18H12IN3O8S2

  • Mr = 589.33

  • Monoclinic, P 21 /c

  • a = 12.1680 (2) Å

  • b = 18.6695 (4) Å

  • c = 9.0443 (2) Å

  • β = 100.030 (2)°

  • V = 2023.20 (7) Å3

  • Z = 4

  • Dx = 1.935 Mg m−3

  • Mo Kα radiation

  • μ = 1.84 mm−1

  • T = 120 (2) K

  • Block, colourless

  • 0.10 × 0.10 × 0.10 mm
Data collection

  • Bruker–Nonius KappaCCD diffractometer

  • φ and ω scans

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. Version 2.10. University of Göttingen, Germany.]) Tmin = 0.837, Tmax = 0.837

  • 27333 measured reflections

  • 4612 independent reflections

  • 3902 reflections with I > 2σ(I)

  • Rint = 0.054

  • θmax = 27.5°
Refinement

  • Refinement on F2

  • R[F2 > 2σ(F2)] = 0.029

  • wR(F2) = 0.067

  • S = 1.08

  • 4612 reflections

  • 289 parameters

  • H-atom parameters constrained

  • w = 1/[σ2(Fo2) + (0.0306P)2 + 0.9151P] where P = (Fo2 + 2Fc2)/3

  • (Δ/σ)max = 0.002

  • Δρmax = 0.88 e Å−3

  • Δρmin = −0.99 e Å−3

Table 1
Selected bond and torsion angles (°)

S1—N1—S2 119.72 (11)
S1—N1—C1 120.03 (15)
S2—N1—C1 120.01 (15)
C2—C1—N1—S1 104.7 (2)
C1—N1—S1—C11 −98.87 (18)
N1—S1—C11—C12 −127.7 (2)
C11—C12—N12—O121 −68.9 (3)
C2—C1—N1—S2 −69.6 (3)
C1—N1—S2—C21 −94.31 (18)
N1—S2—C21—C22 166.42 (19)
C21—C22—N22—O221 27.3 (3)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C2—H2⋯O221i 0.95 2.57 3.185 (3) 123
C13—H13⋯O21ii 0.95 2.44 3.386 (3) 171
C14—H14⋯O22iii 0.95 2.46 3.336 (3) 153
C15—H15⋯O222i 0.95 2.58 3.462 (3) 155
C23—H23⋯O22iv 0.95 2.53 3.475 (3) 172
C26—H26⋯O11v 0.95 2.50 3.230 (3) 134
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x, y, z+1; (iii) -x+1, -y+1, -z+2; (iv) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (v) -x, -y+1, -z+1.

The space group P21/c was uniquely determined from the systematic absences. All H atoms were located in difference maps and then treated as riding atoms, with C—H distances of 0.95 Å and Uiso(H) values of 1.2Ueq(C).

Data collection: COLLECT (Nonius, 1997[Nonius (1997). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999[Ferguson, G. (1999). PRPKAPPA. University of Guelph, Canada.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S0108270106019408/sk3028sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S0108270106019408/sk3028Isup2.hkl


Comment top

We report here the structure of N,N-bis-(2-nitrophenylsulfonyl)-4-iodoaniline, (I) (Fig. 1), where the supramolecular aggregation proves to be markedly different from that in the isomeric compound N,N-bis-(3-nitrophenylsulfonyl)-4-iodoaniline, (II), which was reported recently as part of a wider study of intermolecular interactions in iodonitroarenesulfonamides (Kelly et al., 2002). In (II), the molecules lie across twofold rotation axes in space group C2/c, and they are linked into sheets by a combination of a C—H···O═S hydrogen bond and a three-centre iodo–sulfonyl interaction, but the nitro O atoms play no role in the intermolecular aggregation.

In the title compound, (I), the molecules have planar coordination at atom N1. The molecular conformation is defined by eight torsion angles (Table 1), and these show that the molecules do not exhibit even approximate rotational symmetry; in particular, the orientations of the nitrated aryl rings and the nitro groups are very different for the two independent 2-nitrophenylsulfonyl units within the molecule.

There are no iodo–nitro or iodo–sulfonyl interactions nor aromatic π–π stacking interactions in the structure of (I); instead the molecules are linked into a complex three-dimensional framework by a combination of six independent C—H···O hydrogen bonds (Table 2). However, the formation of the structure of (I) can be analysed in terms of three one-dimensional substructures.

In the first substructure, which is built from the two shortest hydrogen bonds, atoms C13 and C14 in the molecule at (x, y, z) act as donors, respectively, to atoms O21 and O22 in the molecules at (x, y, 1 + z) and (1 − x, 1 − y, 2 − z), and propagation by translation and inversion of these two hydrogen bonds generates a chain of edge-fused rings running parallel to the [001] direction, with R22(18) rings (Bernstein et al., 1995) centred at (1/2, 1/2, n) (n = zero or integer) and R44(14) rings centred at (1/2, 1/2, 0.5 + n) (n = zero or integer) (Fig. 2).

The second substructure depends solely on inversion operations. Atoms C2 and C15 in the molecule at (x, y, z) act as hydrogen-bond donors, respectively, to nitro atoms O221 and O222 in the molecule at (1 − x, 1 − y, 1 − z), so forming a centrosymmetric motif in which an R22(22) ring surrounds an R22(18) ring (Fig. 3). At the same time, atom C26 at (x, y, z) acts as hydrogen-bond donor to sulfonyl atom O11 in the molecule at (−x, 1 − y, 1 − z), so forming a centrosymmetric R22(14) motif, and propagation by inversion of these three hydrogen bonds generates a chain of edge-fused rings running parallel to the [100] direction, with R22(18) and R22(22) rings centred at (1/2 + n, 1/2, 1/2) (n = zero or integer) and R22(14) rings centred at (n, 1/2, 1/2) (n = zero or integer) (Fig. 4).

The combination of the [001] and [100] chains (Figs. 2 and 4) generates a sheet lying parallel to (010) and occupying the domain 0.25 < y < 0.75; a second sheet, related to the first by the action of the translational symmetry elements, occupies the domain −0.25 < y < 1/4, and the action of the third and final one-dimensional substructure is to link adjacent (010) sheets. Atom C23 in the molecule at (x, y, z), which forms part of the sheet in the domain 0.25 < y < 3/4, acts as hydrogen-bond donor to sulfonyl atom O22 in the molecule at (x, 1/2 − y, −1/2 + z), which itself forms part of the sheet in the domain −0.25 < y < 0.25. Hence propagation of this hydrogen bond produces a C(6) chain running parallel to the [010] direction and generated by the c-glide plane at y = 0.25 (Fig. 5), whose effect is to link adjacent (010) sheets, thereby forming a continuous three-dimensional framework structure.

The C—H···O hydrogen bonds in (I) (Table 2) utilize three of the four sulfonyl O atoms as acceptors, with O22 acting as a double acceptor; while both O atoms of one of the nitro groups are employed as hydrogen-bond acceptors, those in the other nitro group play no role in the supramolecular aggregation. In almost all respects, therefore, the direction-specific intermolecular interactions in isomers (I) and (II) are different, leading to markedly different supramolecular structures.

Experimental top

A solution of 2-nitrophenylsulfonyl chloride (1.11 g, 5 mmol), 4-iodoaniline (0.55 g 2.5 mmol) and triethylamine (2 ml) in 1,2-dichloroethane (20 ml) was heated under reflux for 0.5 h; the mixture was then cooled and the solvent was removed under reduced pressure. The resulting solid product was purified by column chromatography on alumina using ethyl acetate as the eluant and then recrystallized from ethanol [m.p. 494–495 K (decomposition)]. NMR (CDCl3): δ(H) 6.76 (d, 2H, J = 8.9 Hz) and 7.75 (d, J = 8.9 Hz) (C6H4I group), 7.63 (dd, 2H, J = 7.9 and 1.4 Hz), 7.74 (dt, 2H, J = 7.9 and 1.4 Hz), 7.79 (dt, 2H, J = 7.9 and 1.4 Hz), 8.22 (dd, 2H, J = 7.9 and 1.4 Hz) (C6H4NO2 groups); IR (KBr disk, cm−1) 1537, 1479, 1464, 1442, 1389, 1367, 1269, 1199, 1169, 1145, 1122, 1057, 1009, 958, 930, 900, 850, 807, 778, 740, 698, 653, 612, 586, 535, 414.

Refinement top

The space group P21/c was uniquely determined from the systematic absences. All H atoms were located in difference maps and then treated as riding atoms with C—H distances of 0.95 Å and Uiso(H) values of 1.2Ueq(C).

Computing details top

Data collection: COLLECT (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

Figures top
[Figure 1] Fig. 1. A view of the molecule of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. A stereoview of part of the crystal structure of (I), showing the formation of a hydrogen-bonded chain along [001] built from alternating R22(18) and R44(14) rings. For the sake of clarity, H atoms not involved in the motif shown have been omitted.
[Figure 3] Fig. 3. Part of the crystal structure of (I), showing the formation of two concentric ring motifs. For the sake of clarity, H atoms not involved in the motifs shown have been omitted. Atoms marked with an asterisk (*) are at the symmetry position (1 − x, 1 − y, 1 − z).
[Figure 4] Fig. 4. A stereoview of part of the crystal structure of (I), showing the formation of a hydrogen-bonded chain along [100] built from R22(18) and R22(22) rings alternating with R44(14) rings. For the sake of clarity, H atoms not involved in the motif shown have been omitted.
[Figure 5] Fig. 5. Part of the crystal structure of (I), showing the formation of a C(6) hydrogen-bonded chain along [010], which links adjacent (010) sheets. For the sake of clarity, H atoms not involved in the motif shown have been omitted. Atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (x, 1/2 − y, −1/2 + z) and (x, 1/2 − y, 1/2 + z), respectively.
4-iodophenylimino bis(2-nitrobenzenesulfinate) top
Crystal data top
C18H12IN3O8S2F(000) = 1160
Mr = 589.33Dx = 1.935 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4612 reflections
a = 12.1680 (2) Åθ = 3.2–27.5°
b = 18.6695 (4) ŵ = 1.84 mm−1
c = 9.0443 (2) ÅT = 120 K
β = 100.030 (2)°Block, colourless
V = 2023.20 (7) Å30.10 × 0.10 × 0.10 mm
Z = 4
Data collection top
Bruker–Nonius KappaCCD
diffractometer		4612 independent reflections
Radiation source: Bruker–Nonius FR591 rotating anode3902 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.054
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.2°
ϕ and ω scansh = −15→15
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		k = −24→24
Tmin = 0.837, Tmax = 0.837l = −11→11
4612 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.067H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0306P)2 + 0.9151P]
where P = (Fo2 + 2Fc2)/3
4612 reflections(Δ/σ)max = 0.002
289 parametersΔρmax = 0.88 e Å−3
0 restraintsΔρmin = −0.99 e Å−3
Crystal data top
C18H12IN3O8S2V = 2023.20 (7) Å3
Mr = 589.33Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.1680 (2) ŵ = 1.84 mm−1
b = 18.6695 (4) ÅT = 120 K
c = 9.0443 (2) Å0.10 × 0.10 × 0.10 mm
β = 100.030 (2)°
Data collection top
Bruker–Nonius KappaCCD
diffractometer		4612 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		3902 reflections with I > 2σ(I)
Tmin = 0.837, Tmax = 0.837Rint = 0.054
4612 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0290 restraints
wR(F2) = 0.067H-atom parameters constrained
S = 1.08Δρmax = 0.88 e Å−3
4612 reflectionsΔρmin = −0.99 e Å−3
289 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.23101 (19)0.54803 (12)0.3959 (3)0.0135 (5)
C20.31765 (18)0.59562 (12)0.3932 (3)0.0144 (5)
C30.30537 (19)0.65045 (12)0.2883 (3)0.0154 (5)
C40.20628 (19)0.65658 (12)0.1879 (3)0.0154 (5)
I40.191490 (13)0.739379 (9)0.029339 (18)0.02137 (7)
C50.11927 (19)0.60854 (13)0.1890 (3)0.0177 (5)
C60.13221 (19)0.55365 (13)0.2938 (3)0.0167 (5)
N10.24333 (15)0.49179 (10)0.5086 (2)0.0129 (4)
S10.17704 (5)0.49852 (3)0.65794 (6)0.01430 (13)
O110.09661 (13)0.55381 (9)0.61739 (18)0.0196 (4)
O120.14369 (14)0.42830 (9)0.69149 (18)0.0190 (4)
S20.33257 (5)0.42391 (3)0.49973 (6)0.01322 (12)
O210.40777 (13)0.44774 (9)0.40493 (18)0.0175 (4)
O220.37124 (13)0.40379 (9)0.65175 (18)0.0180 (4)
C110.27774 (18)0.53079 (13)0.8083 (3)0.0156 (5)
C120.30062 (19)0.49762 (13)0.9478 (3)0.0174 (5)
N120.2400 (2)0.43414 (13)0.9879 (2)0.0286 (5)
O1210.14275 (18)0.44289 (13)1.0005 (2)0.0434 (6)
O1220.2925 (2)0.37852 (12)1.0120 (3)0.0492 (6)
C130.3805 (2)0.52472 (14)1.0615 (3)0.0212 (5)
C140.4373 (2)0.58681 (14)1.0363 (3)0.0208 (5)
C150.4137 (2)0.62090 (14)0.8996 (3)0.0228 (5)
C160.3340 (2)0.59292 (13)0.7850 (3)0.0209 (5)
C210.24879 (19)0.35493 (12)0.4005 (3)0.0143 (5)
C220.29488 (19)0.29462 (13)0.3419 (3)0.0167 (5)
N220.41559 (17)0.28189 (11)0.3645 (2)0.0193 (4)
O2210.47346 (14)0.30665 (10)0.4758 (2)0.0293 (4)
O2220.45171 (17)0.24682 (11)0.2693 (3)0.0379 (5)
C230.2286 (2)0.24305 (13)0.2600 (3)0.0218 (6)
C240.1139 (2)0.25092 (14)0.2355 (3)0.0243 (6)
C250.0670 (2)0.30995 (13)0.2905 (3)0.0212 (5)
C260.13333 (19)0.36139 (13)0.3726 (3)0.0171 (5)
H20.38530.59080.46290.017*
H30.36440.68340.28540.018*
H50.05180.61320.11890.021*
H60.07380.52010.29570.020*
H130.39630.50111.15590.025*
H140.49250.60581.11360.025*
H150.45190.66380.88340.027*
H160.31830.61650.69070.025*
H230.26170.20270.22110.026*
H240.06760.21560.18070.029*
H25−0.01180.31550.27200.025*
H260.09940.40170.41040.020*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0172 (12)0.0116 (11)0.0121 (11)0.0010 (9)0.0035 (9)−0.0001 (9)
C20.0126 (11)0.0168 (12)0.0133 (12)−0.0009 (9)0.0011 (9)−0.0035 (9)
C30.0162 (12)0.0151 (12)0.0154 (12)−0.0009 (9)0.0047 (9)−0.0029 (9)
C40.0198 (12)0.0142 (12)0.0127 (12)0.0027 (9)0.0045 (9)0.0018 (9)
I40.02668 (11)0.01917 (11)0.01761 (10)−0.00077 (6)0.00204 (7)0.00583 (6)
C50.0160 (12)0.0196 (13)0.0158 (12)0.0004 (9)−0.0018 (9)0.0016 (10)
C60.0153 (12)0.0168 (12)0.0176 (12)−0.0025 (9)0.0015 (9)0.0001 (10)
N10.0132 (10)0.0133 (10)0.0123 (10)0.0016 (7)0.0024 (7)0.0003 (7)
S10.0149 (3)0.0157 (3)0.0125 (3)−0.0001 (2)0.0028 (2)−0.0009 (2)
O110.0168 (9)0.0235 (9)0.0188 (9)0.0049 (7)0.0041 (7)−0.0022 (7)
O120.0224 (9)0.0187 (9)0.0164 (9)−0.0053 (7)0.0042 (7)0.0006 (7)
S20.0131 (3)0.0128 (3)0.0132 (3)0.0010 (2)0.0006 (2)0.0000 (2)
O210.0137 (8)0.0202 (9)0.0193 (9)0.0003 (6)0.0049 (7)0.0009 (7)
O220.0213 (9)0.0170 (9)0.0137 (9)0.0016 (6)−0.0024 (7)0.0001 (7)
C110.0155 (12)0.0182 (12)0.0133 (12)0.0009 (9)0.0032 (9)−0.0034 (9)
C120.0194 (13)0.0194 (13)0.0147 (12)0.0022 (9)0.0067 (10)0.0001 (9)
N120.0384 (14)0.0317 (14)0.0151 (12)−0.0108 (10)0.0031 (10)0.0003 (10)
O1210.0441 (14)0.0587 (15)0.0329 (12)−0.0250 (11)0.0224 (10)−0.0121 (10)
O1220.0648 (15)0.0269 (13)0.0483 (14)−0.0084 (11)−0.0112 (11)0.0157 (11)
C130.0243 (13)0.0275 (14)0.0120 (12)0.0042 (10)0.0037 (10)−0.0021 (10)
C140.0179 (12)0.0277 (14)0.0161 (13)0.0017 (10)0.0009 (10)−0.0070 (10)
C150.0237 (13)0.0215 (14)0.0237 (14)−0.0052 (10)0.0057 (11)−0.0071 (11)
C160.0272 (14)0.0194 (13)0.0159 (13)−0.0007 (10)0.0030 (10)0.0000 (10)
C210.0183 (12)0.0130 (11)0.0115 (11)−0.0012 (9)0.0024 (9)0.0013 (9)
C220.0162 (12)0.0165 (13)0.0172 (13)0.0000 (9)0.0024 (9)0.0012 (9)
N220.0191 (11)0.0148 (10)0.0248 (12)0.0018 (8)0.0061 (9)−0.0006 (9)
O2210.0202 (10)0.0328 (11)0.0317 (11)0.0064 (8)−0.0049 (8)−0.0085 (9)
O2220.0243 (11)0.0419 (13)0.0500 (15)0.0019 (8)0.0132 (10)−0.0235 (10)
C230.0257 (14)0.0176 (13)0.0224 (14)0.0014 (10)0.0049 (11)−0.0030 (10)
C240.0232 (14)0.0231 (14)0.0250 (15)−0.0057 (10)−0.0004 (11)−0.0071 (11)
C250.0164 (12)0.0239 (14)0.0226 (14)−0.0030 (10)0.0016 (10)−0.0024 (11)
C260.0165 (12)0.0181 (13)0.0166 (12)0.0018 (9)0.0026 (9)−0.0004 (9)
Geometric parameters (Å, º) top
C1—C21.382 (3)C12—N121.474 (3)
C1—C61.386 (3)N12—O1221.219 (3)
C1—N11.453 (3)N12—O1211.220 (3)
C2—C31.386 (3)C13—C141.389 (4)
C2—H20.95C13—H130.95
C3—C41.382 (3)C14—C151.375 (4)
C3—H30.95C14—H140.95
C4—C51.389 (3)C15—C161.392 (3)
C4—I42.095 (2)C15—H150.95
C5—C61.386 (3)C16—H160.95
C5—H50.95C21—C261.389 (3)
C6—H60.95C21—C221.403 (3)
N1—S21.6799 (19)C22—C231.385 (3)
N1—S11.6939 (19)C22—N221.467 (3)
S1—O121.4207 (17)N22—O2211.215 (3)
S1—O111.4257 (17)N22—O2221.223 (3)
S1—C111.770 (2)C23—C241.382 (4)
S2—O221.4239 (17)C23—H230.95
S2—O211.4296 (17)C24—C251.374 (4)
S2—C211.784 (2)C24—H240.95
C11—C161.382 (3)C25—C261.384 (3)
C11—C121.389 (3)C25—H250.95
C12—C131.382 (3)C26—H260.95
C2—C1—C6121.0 (2)C11—C12—N12123.5 (2)
C2—C1—N1119.4 (2)O122—N12—O121125.8 (3)
C6—C1—N1119.6 (2)O122—N12—C12117.4 (2)
C1—C2—C3119.7 (2)O121—N12—C12116.8 (2)
C1—C2—H2120.2C12—C13—C14119.3 (2)
C3—C2—H2120.2C12—C13—H13120.4
C4—C3—C2119.3 (2)C14—C13—H13120.4
C4—C3—H3120.4C15—C14—C13120.1 (2)
C2—C3—H3120.4C15—C14—H14119.9
C3—C4—C5121.4 (2)C13—C14—H14119.9
C3—C4—I4118.17 (17)C14—C15—C16120.3 (2)
C5—C4—I4120.45 (17)C14—C15—H15119.8
C6—C5—C4119.1 (2)C16—C15—H15119.8
C6—C5—H5120.4C11—C16—C15120.1 (2)
C4—C5—H5120.4C11—C16—H16120.0
C5—C6—C1119.6 (2)C15—C16—H16120.0
C5—C6—H6120.2C26—C21—C22117.4 (2)
C1—C6—H6120.2C26—C21—S2120.00 (18)
S1—N1—S2119.72 (11)C22—C21—S2122.58 (17)
S1—N1—C1120.03 (15)C23—C22—C21121.8 (2)
S2—N1—C1120.01 (15)C23—C22—N22115.9 (2)
O12—S1—O11120.95 (10)C21—C22—N22122.3 (2)
O12—S1—N1107.17 (10)O221—N22—O222124.0 (2)
O11—S1—N1104.45 (10)O221—N22—C22118.4 (2)
O12—S1—C11109.58 (11)O222—N22—C22117.5 (2)
O11—S1—C11107.67 (11)C24—C23—C22119.3 (2)
N1—S1—C11106.01 (10)C24—C23—H23120.4
O22—S2—O21121.52 (10)C22—C23—H23120.4
O22—S2—N1105.09 (10)C25—C24—C23119.9 (2)
O21—S2—N1106.30 (9)C25—C24—H24120.0
O22—S2—C21111.03 (10)C23—C24—H24120.0
O21—S2—C21107.00 (10)C24—C25—C26120.7 (2)
N1—S2—C21104.55 (10)C24—C25—H25119.6
C16—C11—C12119.1 (2)C26—C25—H25119.6
C16—C11—S1117.62 (18)C25—C26—C21120.9 (2)
C12—C11—S1123.26 (18)C25—C26—H26119.5
C13—C12—C11121.1 (2)C21—C26—H26119.5
C13—C12—N12115.4 (2)
C6—C1—C2—C30.9 (3)C13—C12—N12—O122−68.3 (3)
N1—C1—C2—C3−178.4 (2)C11—C12—N12—O122114.3 (3)
C1—C2—C3—C40.0 (3)C13—C12—N12—O121108.5 (3)
C2—C3—C4—C5−0.6 (3)C11—C12—N12—O121−68.9 (3)
C2—C3—C4—I4−179.28 (17)C11—C12—C13—C141.1 (4)
C3—C4—C5—C60.4 (4)N12—C12—C13—C14−176.4 (2)
I4—C4—C5—C6179.01 (18)C12—C13—C14—C150.3 (4)
C4—C5—C6—C10.5 (4)C13—C14—C15—C16−1.0 (4)
C2—C1—C6—C5−1.1 (4)C12—C11—C16—C151.0 (4)
N1—C1—C6—C5178.2 (2)S1—C11—C16—C15179.67 (19)
C6—C1—N1—S2111.1 (2)C14—C15—C16—C110.3 (4)
C2—C1—N1—S1104.7 (2)C2—C1—N1—S2−69.6 (3)
C6—C1—N1—S1−74.6 (3)C1—N1—S2—C21−94.31 (18)
C1—N1—S1—O12144.16 (17)O22—S2—C21—C26102.3 (2)
S2—N1—S1—O12−41.53 (15)O21—S2—C21—C26−122.98 (19)
C1—N1—S1—O1114.71 (19)N1—S2—C21—C26−10.5 (2)
S2—N1—S1—O11−170.98 (12)O22—S2—C21—C22−80.8 (2)
C1—N1—S1—C11−98.87 (18)O21—S2—C21—C2253.9 (2)
S2—N1—S1—C1175.44 (14)N1—S2—C21—C22166.42 (19)
C1—N1—S2—O22148.69 (17)C26—C21—C22—C23−0.4 (4)
S1—N1—S2—O22−25.63 (15)S2—C21—C22—C23−177.37 (19)
C1—N1—S2—O2118.67 (19)C26—C21—C22—N22−179.7 (2)
S1—N1—S2—O21−155.64 (12)S2—C21—C22—N223.3 (3)
S1—N1—S2—C2191.37 (14)C23—C22—N22—O221−152.1 (2)
O12—S1—C11—C16169.00 (18)C21—C22—N22—O22127.3 (3)
O11—S1—C11—C16−57.7 (2)C23—C22—N22—O22228.0 (3)
N1—S1—C11—C1653.7 (2)C21—C22—N22—O222−152.6 (2)
O12—S1—C11—C12−12.4 (2)C21—C22—C23—C24−0.1 (4)
O11—S1—C11—C12121.0 (2)N22—C22—C23—C24179.3 (2)
N1—S1—C11—C12−127.7 (2)C22—C23—C24—C250.8 (4)
C16—C11—C12—C13−1.7 (3)C23—C24—C25—C26−1.0 (4)
S1—C11—C12—C13179.69 (18)C24—C25—C26—C210.5 (4)
C16—C11—C12—N12175.6 (2)C22—C21—C26—C250.2 (3)
S1—C11—C12—N12−3.0 (3)S2—C21—C26—C25177.29 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O221i0.952.573.185 (3)123
C13—H13···O21ii0.952.443.386 (3)171
C14—H14···O22iii0.952.463.336 (3)153
C15—H15···O222i0.952.583.462 (3)155
C23—H23···O22iv0.952.533.475 (3)172
C26—H26···O11v0.952.503.230 (3)134
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y, z+1; (iii) −x+1, −y+1, −z+2; (iv) x, −y+1/2, z−1/2; (v) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formulaC18H12IN3O8S2
Mr589.33
Crystal system, space groupMonoclinic, P21/c
Temperature (K)120
a, b, c (Å)12.1680 (2), 18.6695 (4), 9.0443 (2)
β (°) 100.030 (2)
V (Å3)2023.20 (7)
Z4
Radiation typeMo Kα
µ (mm−1)1.84
Crystal size (mm)0.10 × 0.10 × 0.10
Data collection
DiffractometerBruker–Nonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.837, 0.837
No. of measured, independent and
observed [I > 2σ(I)] reflections		4612, 4612, 3902
Rint0.054
(sin θ/λ)max (Å−1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.029, 0.067, 1.08
No. of reflections4612
No. of parameters289
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.88, −0.99

Computer programs: COLLECT (Nonius, 1997), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97 and PRPKAPPA (Ferguson, 1999).

Selected bond and torsion angles (º) top
S1—N1—S2119.72 (11)S2—N1—C1120.01 (15)
S1—N1—C1120.03 (15)
C2—C1—N1—S1104.7 (2)C2—C1—N1—S2−69.6 (3)
C1—N1—S1—C11−98.87 (18)C1—N1—S2—C21−94.31 (18)
N1—S1—C11—C12−127.7 (2)N1—S2—C21—C22166.42 (19)
C11—C12—N12—O121−68.9 (3)C21—C22—N22—O22127.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O221i0.952.573.185 (3)123
C13—H13···O21ii0.952.443.386 (3)171
C14—H14···O22iii0.952.463.336 (3)153
C15—H15···O222i0.952.583.462 (3)155
C23—H23···O22iv0.952.533.475 (3)172
C26—H26···O11v0.952.503.230 (3)134
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y, z+1; (iii) −x+1, −y+1, −z+2; (iv) x, −y+1/2, z−1/2; (v) −x, −y+1, −z+1.
 

Acknowledgements

X-ray data were collected at the EPSRC X-ray Crystallographic Service, University of Southampton, England; the authors thank the staff of the Service for all their help and advice. JLW thanks CNPq and FAPERJ for financial support.

References

First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science Google Scholar
 First citationFerguson, G. (1999). PRPKAPPA. University of Guelph, Canada.  Google Scholar
 First citationKelly, C. J., Skakle, J. M. S., Wardell, J. L., Wardell, S. M. S. V., Low, J. N. & Glidewell, C. (2002). Acta Cryst. B58, 94–108.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationNonius (1997). COLLECT. Nonius BV, Delft, The Netherlands.  Google Scholar
 First citationOtwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.  Google Scholar
 First citationSheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2003). SADABS. Version 2.10. University of Göttingen, Germany.  Google Scholar
 First citationSpek, A. L. (2003). J. Appl. Cryst. 36, 7–13.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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Journal logoSTRUCTURAL
CHEMISTRY
ISSN: 2053-2296
Volume 62| Part 7| July 2006| Pages o423-o425
doi:10.1107/S0108270106019408
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