N-(2-Hydr­oxy-3-iodo-5-nitro­benzyl­idene)-3-nitro­aniline: conformational isomers linked into complex sheets by five C—H⋯O hydrogen bonds and a two-centre iodo–nitro inter­action

Low, J.N.; Skakle, J.M.S.; Garden, S.J.; Wardell, J.L.; Glidewell, C.

doi:10.1107/S0108270106020373

organic compounds

STRUCTURAL
CHEMISTRY

ISSN: 2053-2296

Volume 62| Part 7| July 2006| Pages o441-o443

doi:10.1107/S0108270106020373

N-(2-Hydroxy-3-iodo-5-nitrobenzylidene)-3-nitroaniline: conformational isomers linked into complex sheets by five C—H⋯O hydrogen bonds and a two-centre iodo–nitro interaction

John N. Low,^a Janet M. S. Skakle,^a Simon J. Garden,^b James L. Wardell ^b and Christopher Glidewell ^c ^*

^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 26 May 2006; accepted 30 May 2006; online 30 June 2006)

The title compound, C₁₃H₈IN₃O₅, crystallizes with Z′ = 2 in the space group P2₁/n. The two independent molecules, which are both almost planar, are conformational isomers. The molecules are linked into complex sheets by a combination of five independent C—H⋯O hydrogen bonds and an almost linear two-centre iodo–nitro interaction.

Comment

We have recently reported the supramolecular structures of imines containing iodo and nitro groups, for example, N-(2-iodobenzylidene)-3-nitroaniline, 2-IC₆H₄CH=NC₆H₄NO₂-3′ (Wardell et al., 2002 ), and the various isomeric N-(nitrobenzylidene)iodoanilines, O₂NC₆H₄CH=NC₆H₄I (Glidewell et al., 2002 ), several of which crystallize in two polymorphic forms (Ferguson et al., 2005 ). We have now continued our studies in this area with the title compound, (I), an imine containing an additional nitro group as well as a hard hydrogen-bonding donor group.

Compound (I) crystallizes with Z′ = 2 in the space group P2₁/n (Fig. 1). In each of the independent molecules there is an intramolecular O—H⋯N hydrogen bond, forming an S(6) motif (Bernstein et al., 1995 ), and these interactions undoubtedly influence the molecular conformations. Both molecules are nearly planar. The overall conformation in each is defined by five torsion angles (Table 1), and it is striking that in molecule A the two nitro groups are on the same edge of the molecule, whereas in molecule B these substituents are on opposite edges (Fig. 1). The two molecules are thus conformational isomers, and this alone suffices to preclude any possible additional symmetry.

Within the molecules, the bond distances show some interesting patterns (Table 1), consequent upon the mutually

para arrangement in the iodinated rings of the electron-donor hydroxyl substituent and the electron-acceptor nitro group; in the non-iodinated rings, there is no possibility of any conjugative interactions. Thus, the C—O bonds are significantly shorter than is typical in simple phenols (mean value 1.362 Å; Allen et al., 1987

). Of the C—N bonds to the nitro groups, the bonds C5A—N5A and C5B—N5B are both somewhat shorter than the mean value for simple aromatic nitro compounds (1.468 Å), whereas the bonds C13A—N13A and C13B—N13B are both considerably longer. The N—O bonds involving atoms N5A and N5B are shorter than those involving atoms N13A and N13B. Finally, there is some evidence of C—C bond fixation within the iodinated rings. These observations, taken together, provide some evidence in favour of polarized form (Ia)

(see scheme) as a modest contributor to the overall molecular electronic structure.

Within the selected asymmetric unit, the two molecules are linked by two C—H⋯O hydrogen bonds (Fig. 1 and Table 2), and this bimolecular aggregate can be regarded as the basic building block within the supramolecular structure. Three further C—H⋯O hydrogen bonds and a two-centre iodo–nitro interaction then link these aggregates into complex sheets, the formation of which can be readily analysed in terms of one-dimensional substructures.

In the principal substructure, atom C14B at (x, y, z) acts as hydrogen-bond donor to atom O14B at (−x, −y, 1 − z), so generating by inversion a centrosymmetric R₂²(10) motif centred at (0, 0, $[{1 \over 2}]$ ). At the same time, atom I3B at (x, y, z) forms a two-centre interaction with atom O13A at (−x, 1 − y, 1 − z), with dimensions I⋯O = 3.173 (4) Å and C—I⋯O = 175.6 (2)°, so generating by inversion an R₄⁴(28) (Starbuck et al., 1999 ) motif centred at (0, $[{1 \over 2}]$ , $[{1 \over 2}]$ ). Propagation by inversion of these two interactions then generates a chain running parallel to the [010] direction containing R₂²(10) rings centred at (0, n, $[{1 \over 2}]$ ) (n = zero or integer) and R₄⁴(28) rings centred at (0, n + $[{1 \over 2}]$ , $[{1 \over 2}]$ ) (n = zero or integer), together with two types of S(6) ring and an R₂²(14) ring (Fig. 2).

Two further C—H⋯O hydrogen bonds link the [010] chains into sheets. The type A molecules (Fig. 1) at (x, y, z) and (−x, −y, 1 − z) form part of the chain along (0, y, $[{1 \over 2}]$ ) (Fig. 2). The C14A atoms at (x, y, z) and (−x, −y, 1 − z), act as hydrogen-bond donors to, respectively, atoms O51A at ( $[{3\over 2}]$ − x, $[{1\over 2}]$ + y, $[{1\over 2}]$ − z) and (− $[{3\over 2}]$ + x, − $[{1\over 2}]$ − y, $[{1\over 2}]$ + z), which themselves lie in the [010] chains along ( $[{3 \over 2}]$ , y, 0) and ( $[-{3 \over 2}]$ , y, 1), respectively. Hence, the propagation of this hydrogen bond by the 2₁ screw axes along [3(2m + 1)/4, y, (1 − 2m)/4] (m = zero or integer) links the [010] chains into a (103) sheet. The formation of this sheet is reinforced by the final C—H⋯O hydrogen bond, in which atom C16A at (x, y, z) acts as hydrogen-bond donor to atom O13B at ( $[{3\over 2}]$ + x, $[{1\over 2}]$ − y, − $[{1\over 2}]$ + z), so forming a C₂²(18)C₂²(18)[R₂²(14)] chain of rings running parallel to the [30 $[\overline{1}]$ ] direction and generated by the n-glide plane at y = $[{1 \over 4}]$ (Fig. 3).

There are no direction-specific interactions between adjacent sheets. In particular, C—H⋯π(arene) hydrogen bonds and aromatic π–π stacking interactions are absent from the structure of (I).

Figure 1
The two independent molecules of compound (I)

, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii. The intramolecular O—H⋯N hydrogen bonds and the two C—H⋯O hydrogen bonds within the selected asymmetric unit are indicated by dashed lines.

Figure 2
A stereoview of part of the crystal structure of compound (I)

, showing the formation of a chain along [010] built from hydrogen bonds and iodo–nitro interactions, and containing five different rings. For the sake of clarity, H atoms not involved in the motifs shown have been omitted.

Figure 3
A stereoview of part of the crystal structure of compound (I)

, showing the formation of a hydrogen-bonded chain of rings along [30 $[\overline{1}]$ ]. For the sake of clarity, H atoms not involved in the motifs shown have been omitted.

Experimental

A solution of 3-nitroaniline (1.38 g, 10 mmol) and 2-hydroxy-3-iodo-5-nitrobenzaldehyde (0.55 g, 10 mmol) (Garden et al., 2004 ) in methanol (30 ml) was heated under reflux for 45 min. The mixture was then cooled and the solvent was removed under reduced pressure. Crystallization from ethanol of the resulting solid product gave crystals of (I) suitable for single-crystal X-ray diffraction.

Crystal data

C₁₃H₈IN₃O₅
M_r = 413.12
Monoclinic, P 2₁ /n
a = 9.2957 (4) Å
b = 27.5905 (13) Å
c = 11.0084 (5) Å
β = 93.830 (2)°
V = 2817.1 (2) Å³
Z = 8
D_x = 1.948 Mg m⁻³
Mo Kα radiation
μ = 2.30 mm⁻¹
T = 291 (2) K
Plate, colourless
0.30 × 0.22 × 0.05 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
φ and ω scans
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.545, T_max = 0.893
29048 measured reflections
10158 independent reflections
4201 reflections with I > 2σ(I)
R_int = 0.068
θ_max = 32.5°

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.093
S = 0.87
10158 reflections
399 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0298P)²] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max = 0.001
Δρ_max = 0.72 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

C1A—C2A	1.411 (5)
C2A—C3A	1.406 (5)
C3A—C4A	1.377 (5)
C4A—C5A	1.387 (5)
C5A—C6A	1.380 (5)
C6A—C1A	1.394 (5)
C2A—O2A	1.327 (4)
C5A—N5A	1.457 (5)
N5A—O51A	1.217 (4)
N5A—O52A	1.229 (4)
C13A—N13A	1.484 (5)
N13A—O13A	1.198 (5)
N13A—O14A	1.207 (4)
C1B—C2B	1.419 (5)
C2B—C3B	1.414 (5)
C3B—C4B	1.368 (5)
C4B—C5B	1.388 (5)
C5B—C6B	1.359 (5)
C6B—C1B	1.388 (5)
C2B—O2B	1.311 (4)
C5B—N5B	1.463 (5)
N5B—O51B	1.204 (4)
N5B—O52B	1.232 (4)
C13B—N13B	1.475 (5)
N13B—O13B	1.215 (5)
N13B—O14B	1.208 (4)

C12A—C13A—N13A—O13A	−7.1 (7)
C1A—C7A—N1A—C11A	−177.1 (4)
N1A—C7A—C1A—C2A	0.4 (7)
C7A—N1A—C11A—C12A	−0.1 (7)
C4A—C5A—N5A—O51A	8.2 (6)
C12B—C13B—N13B—O13B	5.5 (7)
C1B—C7B—N1B—C11B	−179.4 (4)
N1B—C7B—C1B—C2B	1.1 (6)
C7B—N1B—C11B—C12B	176.9 (4)
C4B—C5B—N5B—O51B	1.2 (7)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2A—H2A⋯N1A	0.82	1.85	2.580 (4)	148
O2B—H2B⋯N1B	0.82	1.81	2.549 (4)	149
C7A—H7A⋯O52B	0.93	2.37	3.263 (5)	160
C7B—H7B⋯O52A	0.93	2.36	3.254 (5)	162
C14A—H14A⋯O51Aⁱ	0.93	2.53	3.372 (6)	151
C14B—H14B⋯O14Bⁱⁱ	0.93	2.51	3.279 (6)	141
C16A—H16A⋯O13Bⁱⁱⁱ	0.93	2.47	3.377 (5)	166
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x, -y, -z+1; (iii) $[x+{\script{3\over 2}}]$ , $[-y+{\script{1\over 2}}]$ , $[z-{\script{1\over 2}}]$ .

The space group P2₁/n was uniquely assigned from the systematic absences. All H atoms were located in difference maps and then treated as riding atoms, with C—H = 0.93 Å, O—H = 0.82 Å and U_iso(H) = 1.2U_eq(C) or 1.5U_eq(O).

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S0108270106020373/sk3030sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S0108270106020373/sk3030Isup2.hkl

Comment top

We have recently reported the supramolecular structures of imines containing iodo and nitro groups, for example N-(2-iodobenzylidene)-3-nitroaniline, 2-IC₆H₄CH═ NC₆H₄NO₂-3' (Wardell et al., 2002), and the various isomeric N-(nitrobenzylidene)iodoanilines, O₂NC₆H₄CH═NC₆H₄I (Glidewell et al., 2002), several of which crystallize in two polymorphic forms (Ferguson et al., 2005). We have now continued our studies in this area with the title compound, (I), an imine containing an additional nitro group as well as a hard hydrogen-bonding donor group.

Compound (I) crystallizes with Z' = 2 in space group P2₁/n (Fig. 1). In each of the independent molecules there is an intramolecular O—H···N hydrogen bond, forming an S(6) motif (Bernstein et al., 1995), and these interactions undoubtedly influence the molecular conformations. Both molecules are nearly planar. The overall conformation in each is defined by five torsion angles (Table 1), and it is striking that in molecule A (Fig. 1) the two nitro groups are on the same edge of the molecule, whereas in molecule B these substituents are on opposite edges. The two molecules are thus conformational isomers, and this alone suffices to preclude any possible additional symmetry.

Within the molecules, the bond distances show some interesting patterns (Table 1), consequent upon the mutually para arrangement in the iodinated rings of the electron-donor hydroxyl substituent and the electron-acceptor nitro group; in the non-iodinated rings, there is no possibility of any conjugative interactions. Thus, the C—O bonds are significantly shorter than is typical in simple phenols (mean value 1.362 Å; Allen et al., 1987). Of the C—N bonds to the nitro groups, the bonds C5A—N5A and C5B—N5B are both somewhat shorter than the mean value for simple aromatic nitro compounds (1.468 Å), whereas the bonds C13A—N13A and C13B—N13B are both considerably longer. The N—O bonds involving atoms N5A and N5B are consistently shorter than those involving atoms N13A and N13B. Finally, there is some evidence of C—C bond fixation within the iodinated rings. These observations, taken together, provide some evidence in favour of the polarized form, (Ia), as a modest contributor to the overall molecular electronic structure.

Within the selected asymmetric unit, the two molecules are linked by two C—H···O hydrogen bonds (Fig. 1, Table 2), and this bimolecular aggregate can be regarded as the basic building block within the supramolecular structure. Three further C—H···O hydrogen bonds and a two-centre iodo···nitro interaction then link these aggregates into complex sheets, the formation of which can be readily analysed in terms of one-dimensional sub-structures.

In the principal sub-structure, atom C14B at (x, y, z) acts as hydrogen-bond donor to atom O14B at (−x, −y, 1 − z), so generating by inversion a centrosymmetric R²₂(10) motif centred at (0, 0, 1/2). At the same time, atom I3B at (x, y, z) forms a two-centre interaction with atom O13A at (−x, 1 − y, 1 − z), with dimensions I···Oⁱ = 3.173 (4) Å and C—I···Oⁱ = 175.6 (2)° [symmetry code: (i) −x, 1 − y, 1 − z], so generating by inversion an R⁴₄(28) (Starbuck et al., 1999) motif centred at (0, 1/2, 1/2). Propagation by inversion of these two interactions then generates a chain running parallel to the [010] direction containing R²₂(10) rings centred at (0, n, 1/2) (n = zero or integer) and R⁴₄(28) rings centred at (0, n + 1/2, 1/2) (n = zero or integer), together with two types of S(6) ring and an R²₂(14) ring (Fig. 2).

Two further C—H···O hydrogen bonds link the [010] chains into sheets. The type A molecules (Fig. 1) at (x, y, z) and (−x, −y, 1 − z) form part of the chain along (0, y, 1/2) (Fig. 2). The atoms C14A at (x, y, z) and (−x, −y, 1 − z), act as hydrogen-bond donors to, respectively, atoms O51A at (3/2 − x, 1/2 + y, 1/2 − z) and (−3/2 + x, −1/2 − y, 1/2 + z), which themselves lie in the [010] chains along (3/2, y, 0) and (−3/2, y, 1), respectively. Hence, the propagation of this hydrogen bond by the 2₁screw axes along [3(2m + 1)/4, y, (1 − 2m)/4] (m = zero or integer) links the [010] chains into a (103) sheet. The formation of this sheet is reinforced by the final C—H···O hydrogen bond, in which atom C16A at (x, y, z) acts as hydrogen-bond donor to atom O13B at (3/2 + x, 1/2 − y, −1/2 + z), so forming a C²₂(18) C²₂(18)[R²₂(14)] chain of rings running parallel to the [301] direction and generated by the n-glide plane at y = 1/4 (Fig. 3).

There are no direction-specific interactions between adjacent sheets. In particular, C—H···π(arene) hydrogen bonds and aromatic π–π stacking interactions are absent from the structure of (I).

Experimental top

A solution of 3-nitroaniline (1.38 g, 10 mmol) and 2-hydroxy-3-iodo-5-nitrobenzaldehyde (0.55 g, 10 mmol) (Garden et al., 2004) in methanol (30 ml) was heated under reflux for 45 min. The mixture was then cooled and the solvent was removed under reduced pressure. Crystallization from ethanol of the resulting solid product gave crystals of (I) suitable for single-crystal X-ray diffraction.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; 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

	Fig. 1. The two independent molecules of compound (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii. The intramolecular O—H···N hydrogen bonds and the two C—H.·O hydrogen bonds within the selected asymmetric unit are indicated by dashed lines.
	Fig. 2. A stereoview of part of the crystal structure of compound (I), showing the formation of a chain along [010] built from hydrogen bonds and iodo···nitro interactions, and containing five different rings. For the sake of clarity, H atoms not involved in the motifs shown have been omitted.
	Fig. 3. A stereoview of part of the crystal structure of compound (I), showing the formation of a hydrogen-bonded chain of rings along [301]. For the sake of clarity, H atoms not involved in the motifs shown have been omitted.

N-(2-Hydroxy-3-iodo-5-nitrobenzylidene)-3-nitroaniline top

Crystal data top

C₁₃H₈IN₃O₅	F(000) = 1600
M_r = 413.12	D_x = 1.948 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 10158 reflections
a = 9.2957 (4) Å	θ = 2.0–32.5°
b = 27.5905 (13) Å	µ = 2.30 mm⁻¹
c = 11.0084 (5) Å	T = 291 K
β = 93.830 (2)°	Plate, colourless
V = 2817.1 (2) Å³	0.30 × 0.22 × 0.05 mm
Z = 8

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	10158 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	4201 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.068
ϕ/ω scans	θ_max = 32.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −12→14
T_min = 0.545, T_max = 0.893	k = −41→40
29048 measured reflections	l = −14→16

Refinement top

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) = 0.093	H-atom parameters constrained
S = 0.87	w = 1/[σ²(F_o²) + (0.0298P)²] where P = (F_o² + 2F_c²)/3
10158 reflections	(Δ/σ)_max = 0.001
399 parameters	Δρ_max = 0.72 e Å⁻³
0 restraints	Δρ_min = −0.51 e Å⁻³

Crystal data top

C₁₃H₈IN₃O₅	V = 2817.1 (2) Å³
M_r = 413.12	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.2957 (4) Å	µ = 2.30 mm⁻¹
b = 27.5905 (13) Å	T = 291 K
c = 11.0084 (5) Å	0.30 × 0.22 × 0.05 mm
β = 93.830 (2)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	10158 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	4201 reflections with I > 2σ(I)
T_min = 0.545, T_max = 0.893	R_int = 0.068
29048 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.093	H-atom parameters constrained
S = 0.87	Δρ_max = 0.72 e Å⁻³
10158 reflections	Δρ_min = −0.51 e Å⁻³
399 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1A	0.7396 (4)	0.32517 (14)	0.2209 (4)	0.0415 (10)
C2A	0.8625 (4)	0.30384 (15)	0.1745 (4)	0.0421 (10)
C3A	0.8740 (4)	0.25305 (14)	0.1702 (4)	0.0409 (10)
C4A	0.7664 (4)	0.22415 (14)	0.2109 (4)	0.0437 (10)
C5A	0.6448 (4)	0.24585 (14)	0.2533 (4)	0.0417 (10)
C6A	0.6301 (4)	0.29554 (15)	0.2596 (4)	0.0424 (10)
O2A	0.9685 (3)	0.33075 (10)	0.1356 (3)	0.0554 (8)
I3A	1.06008 (3)	0.222130 (10)	0.10789 (3)	0.05289 (10)
N5A	0.5291 (4)	0.21515 (14)	0.2923 (3)	0.0538 (10)
O51A	0.5482 (3)	0.17160 (12)	0.2999 (4)	0.0795 (11)
O52A	0.4151 (3)	0.23460 (11)	0.3152 (3)	0.0687 (10)
C7A	0.7259 (4)	0.37732 (14)	0.2311 (4)	0.0473 (11)
N1A	0.8246 (3)	0.40571 (12)	0.1978 (3)	0.0481 (9)
C11A	0.8200 (4)	0.45685 (14)	0.2106 (4)	0.0451 (10)
C12A	0.7079 (4)	0.48208 (14)	0.2607 (4)	0.0495 (11)
C13A	0.7214 (4)	0.53096 (14)	0.2715 (4)	0.0514 (11)
C14A	0.8390 (5)	0.55672 (16)	0.2374 (5)	0.0655 (14)
C15A	0.9482 (5)	0.53111 (17)	0.1880 (5)	0.0767 (16)
C16A	0.9380 (5)	0.48180 (17)	0.1743 (5)	0.0642 (14)
N13A	0.6041 (4)	0.55855 (14)	0.3252 (4)	0.0645 (11)
O13A	0.4970 (4)	0.53663 (12)	0.3453 (4)	0.1098 (16)
O14A	0.6206 (4)	0.60154 (12)	0.3412 (4)	0.0835 (12)
C1B	0.0925 (4)	0.30637 (14)	0.4377 (4)	0.0389 (9)
C2B	−0.0316 (4)	0.32694 (15)	0.4857 (4)	0.0430 (10)
C3B	−0.0414 (4)	0.37800 (15)	0.4930 (4)	0.0446 (10)
C4B	0.0665 (4)	0.40661 (15)	0.4539 (4)	0.0495 (11)
C5B	0.1856 (4)	0.38511 (15)	0.4065 (4)	0.0471 (11)
C6B	0.2002 (4)	0.33623 (15)	0.3984 (4)	0.0480 (11)
O2B	−0.1357 (3)	0.29980 (10)	0.5232 (3)	0.0551 (8)
I3B	−0.22515 (3)	0.408833 (11)	0.56081 (3)	0.06011 (11)
N5B	0.3001 (4)	0.41635 (15)	0.3659 (4)	0.0703 (12)
O51B	0.2877 (4)	0.45952 (13)	0.3771 (5)	0.128 (2)
O52B	0.4033 (3)	0.39706 (12)	0.3204 (4)	0.0836 (12)
C7B	0.1070 (4)	0.25474 (15)	0.4298 (4)	0.0446 (10)
N1B	0.0085 (3)	0.22593 (12)	0.4636 (3)	0.0430 (8)
C11B	0.0187 (4)	0.17463 (14)	0.4586 (4)	0.0440 (10)
C12B	−0.0938 (4)	0.14925 (15)	0.5043 (4)	0.0475 (11)
C13B	−0.0864 (4)	0.09943 (15)	0.5059 (4)	0.0507 (11)
C14B	0.0262 (5)	0.07417 (16)	0.4619 (4)	0.0574 (12)
C15B	0.1353 (5)	0.10006 (16)	0.4145 (4)	0.0585 (13)
C16B	0.1336 (4)	0.14985 (16)	0.4124 (4)	0.0514 (11)
N13B	−0.2059 (4)	0.07247 (15)	0.5560 (4)	0.0675 (12)
O13B	−0.3092 (4)	0.09588 (12)	0.5844 (4)	0.0943 (13)
O14B	−0.1970 (4)	0.02889 (12)	0.5645 (4)	0.0867 (12)
H4A	0.7751	0.1906	0.2099	0.052*
H6A	0.5479	0.3091	0.2893	0.051*
H2A	0.9468	0.3595	0.1396	0.083*
H7A	0.6439	0.3904	0.2625	0.057*
H12A	0.6270	0.4660	0.2858	0.059*
H14A	0.8445	0.5902	0.2473	0.079*
H15A	1.0292	0.5473	0.1639	0.092*
H16A	1.0119	0.4650	0.1399	0.077*
H4B	0.0601	0.4402	0.4590	0.059*
H6B	0.2817	0.3229	0.3669	0.058*
H2B	−0.1174	0.2712	0.5111	0.083*
H7B	0.1897	0.2418	0.3995	0.054*
H12B	−0.1725	0.1654	0.5333	0.057*
H14B	0.0285	0.0405	0.4641	0.069*
H15B	0.2119	0.0836	0.3833	0.070*
H16B	0.2086	0.1669	0.3803	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1A	0.031 (2)	0.045 (2)	0.049 (3)	0.0070 (18)	0.0061 (19)	−0.003 (2)
C2A	0.031 (2)	0.050 (3)	0.046 (3)	0.0040 (19)	0.0074 (19)	−0.002 (2)
C3A	0.027 (2)	0.046 (2)	0.050 (3)	0.0050 (18)	0.0087 (19)	0.000 (2)
C4A	0.041 (2)	0.046 (2)	0.045 (3)	0.008 (2)	0.0071 (19)	−0.002 (2)
C5A	0.032 (2)	0.047 (2)	0.047 (3)	−0.0023 (18)	0.0067 (19)	−0.001 (2)
C6A	0.029 (2)	0.055 (3)	0.044 (3)	0.0048 (18)	0.0054 (19)	−0.007 (2)
O2A	0.0409 (16)	0.0458 (16)	0.082 (2)	0.0023 (14)	0.0223 (16)	0.0047 (18)
I3A	0.04261 (16)	0.05769 (18)	0.0606 (2)	0.01476 (14)	0.02029 (14)	0.00158 (16)
N5A	0.041 (2)	0.063 (3)	0.059 (2)	−0.0084 (19)	0.0167 (18)	−0.012 (2)
O51A	0.071 (2)	0.047 (2)	0.125 (3)	−0.0056 (17)	0.042 (2)	0.004 (2)
O52A	0.0349 (16)	0.074 (2)	0.100 (3)	−0.0055 (15)	0.0251 (17)	−0.0183 (19)
C7A	0.040 (2)	0.050 (3)	0.052 (3)	0.008 (2)	0.007 (2)	−0.004 (2)
N1A	0.038 (2)	0.045 (2)	0.062 (2)	0.0051 (16)	0.0080 (17)	0.0005 (19)
C11A	0.036 (2)	0.042 (2)	0.058 (3)	0.0056 (19)	0.009 (2)	−0.002 (2)
C12A	0.038 (2)	0.041 (2)	0.071 (3)	0.0013 (19)	0.015 (2)	0.005 (2)
C13A	0.044 (3)	0.042 (3)	0.069 (3)	0.005 (2)	0.009 (2)	−0.005 (2)
C14A	0.060 (3)	0.044 (3)	0.094 (4)	−0.006 (2)	0.017 (3)	−0.008 (3)
C15A	0.051 (3)	0.060 (3)	0.123 (5)	−0.015 (2)	0.029 (3)	−0.008 (3)
C16A	0.043 (3)	0.062 (3)	0.090 (4)	0.002 (2)	0.023 (3)	−0.001 (3)
N13A	0.060 (3)	0.045 (2)	0.091 (3)	0.009 (2)	0.020 (2)	−0.005 (2)
O13A	0.082 (3)	0.055 (2)	0.202 (5)	0.0031 (19)	0.083 (3)	−0.012 (3)
O14A	0.084 (3)	0.047 (2)	0.120 (3)	0.0045 (18)	0.019 (2)	−0.025 (2)
C1B	0.028 (2)	0.047 (2)	0.042 (3)	−0.0005 (18)	0.0054 (18)	0.000 (2)
C2B	0.035 (2)	0.049 (2)	0.047 (3)	−0.0011 (19)	0.0110 (19)	0.001 (2)
C3B	0.029 (2)	0.058 (3)	0.048 (3)	0.0003 (19)	0.0100 (19)	0.002 (2)
C4B	0.044 (2)	0.046 (2)	0.060 (3)	−0.001 (2)	0.015 (2)	−0.004 (2)
C5B	0.031 (2)	0.051 (3)	0.061 (3)	−0.0104 (19)	0.018 (2)	−0.002 (2)
C6B	0.033 (2)	0.058 (3)	0.055 (3)	−0.0046 (19)	0.014 (2)	−0.005 (2)
O2B	0.0374 (16)	0.0538 (17)	0.077 (2)	−0.0032 (14)	0.0260 (15)	0.0060 (18)
I3B	0.04633 (17)	0.0628 (2)	0.0742 (2)	0.00891 (14)	0.02602 (16)	−0.00050 (17)
N5B	0.046 (2)	0.060 (3)	0.107 (4)	−0.013 (2)	0.027 (2)	0.001 (3)
O51B	0.101 (3)	0.049 (2)	0.246 (6)	−0.021 (2)	0.097 (4)	−0.010 (3)
O52B	0.0451 (19)	0.081 (2)	0.130 (3)	−0.0077 (17)	0.045 (2)	0.005 (2)
C7B	0.036 (2)	0.058 (3)	0.041 (3)	0.002 (2)	0.0105 (19)	−0.004 (2)
N1B	0.0344 (18)	0.050 (2)	0.046 (2)	−0.0031 (16)	0.0094 (16)	0.0010 (18)
C11B	0.043 (2)	0.045 (2)	0.044 (3)	−0.0024 (19)	0.008 (2)	−0.001 (2)
C12B	0.037 (2)	0.049 (3)	0.058 (3)	−0.003 (2)	0.011 (2)	−0.004 (2)
C13B	0.044 (2)	0.052 (3)	0.057 (3)	−0.004 (2)	0.014 (2)	−0.002 (2)
C14B	0.055 (3)	0.050 (3)	0.070 (3)	0.004 (2)	0.017 (3)	0.001 (2)
C15B	0.051 (3)	0.058 (3)	0.068 (3)	0.008 (2)	0.016 (2)	−0.003 (3)
C16B	0.040 (2)	0.057 (3)	0.059 (3)	0.002 (2)	0.019 (2)	0.002 (2)
N13B	0.059 (3)	0.056 (3)	0.091 (3)	−0.013 (2)	0.027 (2)	−0.004 (2)
O13B	0.058 (2)	0.064 (2)	0.167 (4)	−0.0051 (18)	0.055 (2)	−0.003 (2)
O14B	0.088 (3)	0.045 (2)	0.132 (3)	−0.0091 (18)	0.046 (2)	0.004 (2)

Geometric parameters (Å, º) top

C1A—C2A	1.411 (5)	C1B—C2B	1.419 (5)
C2A—C3A	1.406 (5)	C2B—C3B	1.414 (5)
C3A—C4A	1.377 (5)	C3B—C4B	1.368 (5)
C4A—C5A	1.387 (5)	C4B—C5B	1.388 (5)
C5A—C6A	1.380 (5)	C5B—C6B	1.359 (5)
C6A—C1A	1.394 (5)	C6B—C1B	1.388 (5)
C2A—O2A	1.327 (4)	C2B—O2B	1.311 (4)
C5A—N5A	1.457 (5)	C5B—N5B	1.463 (5)
N5A—O51A	1.217 (4)	N5B—O51B	1.204 (4)
N5A—O52A	1.229 (4)	N5B—O52B	1.232 (4)
C13A—N13A	1.484 (5)	C13B—N13B	1.475 (5)
N13A—O13A	1.198 (5)	N13B—O13B	1.215 (5)
N13A—O14A	1.207 (4)	N13B—O14B	1.208 (4)
C1A—C7A	1.450 (5)	C1B—C7B	1.434 (5)
C3A—I3A	2.086 (3)	C3B—I3B	2.090 (4)
C4A—H4A	0.93	C4B—H4B	0.93
C6A—H6A	0.93	C6B—H6B	0.93
O2A—H2A	0.82	O2B—H2B	0.82
C7A—N1A	1.279 (5)	C7B—N1B	1.286 (5)
C7A—H7A	0.93	C7B—H7B	0.93
N1A—C11A	1.419 (5)	N1B—C11B	1.420 (5)
C11A—C16A	1.377 (6)	C11B—C12B	1.381 (5)
C11A—C12A	1.398 (5)	C11B—C16B	1.393 (5)
C12A—C13A	1.359 (5)	C12B—C13B	1.376 (5)
C12A—H12A	0.93	C12B—H12B	0.93
C13A—C14A	1.377 (6)	C13B—C14B	1.372 (5)
C14A—C15A	1.378 (6)	C14B—C15B	1.372 (6)
C14A—H14A	0.93	C14B—H14B	0.93
C15A—C16A	1.372 (6)	C15B—C16B	1.374 (6)
C15A—H15A	0.93	C15B—H15B	0.93
C16A—H16A	0.93	C16B—H16B	0.93

C6A—C1A—C2A	119.4 (4)	C6B—C1B—C2B	120.0 (4)
C6A—C1A—C7A	119.2 (3)	C6B—C1B—C7B	119.9 (3)
C2A—C1A—C7A	121.3 (4)	C2B—C1B—C7B	120.1 (3)
O2A—C2A—C3A	119.2 (3)	O2B—C2B—C3B	120.0 (3)
O2A—C2A—C1A	121.3 (4)	O2B—C2B—C1B	121.6 (4)
C3A—C2A—C1A	119.5 (4)	C3B—C2B—C1B	118.4 (3)
C4A—C3A—C2A	120.5 (3)	C4B—C3B—C2B	120.4 (4)
C4A—C3A—I3A	120.4 (3)	C4B—C3B—I3B	120.8 (3)
C2A—C3A—I3A	119.0 (3)	C2B—C3B—I3B	118.9 (3)
C3A—C4A—C5A	119.0 (4)	C3B—C4B—C5B	119.4 (4)
C3A—C4A—H4A	120.5	C3B—C4B—H4B	120.3
C5A—C4A—H4A	120.5	C5B—C4B—H4B	120.3
C6A—C5A—C4A	122.1 (4)	C6B—C5B—C4B	122.3 (4)
C6A—C5A—N5A	119.0 (3)	C6B—C5B—N5B	119.1 (4)
C4A—C5A—N5A	118.9 (4)	C4B—C5B—N5B	118.6 (4)
C5A—C6A—C1A	119.3 (3)	C5B—C6B—C1B	119.4 (4)
C5A—C6A—H6A	120.3	C5B—C6B—H6B	120.3
C1A—C6A—H6A	120.3	C1B—C6B—H6B	120.3
C2A—O2A—H2A	109.5	C2B—O2B—H2B	109.5
O51A—N5A—O52A	122.8 (4)	O51B—N5B—O52B	123.5 (4)
O51A—N5A—C5A	119.2 (3)	O51B—N5B—C5B	118.3 (4)
O52A—N5A—C5A	118.1 (4)	O52B—N5B—C5B	118.2 (4)
N1A—C7A—C1A	121.1 (4)	N1B—C7B—C1B	121.7 (4)
N1A—C7A—H7A	119.4	N1B—C7B—H7B	119.2
C1A—C7A—H7A	119.4	C1B—C7B—H7B	119.2
C7A—N1A—C11A	123.6 (3)	C7B—N1B—C11B	123.6 (3)
C16A—C11A—C12A	119.7 (4)	C12B—C11B—C16B	120.1 (4)
C16A—C11A—N1A	116.0 (4)	C12B—C11B—N1B	115.9 (3)
C12A—C11A—N1A	124.2 (4)	C16B—C11B—N1B	124.0 (4)
C13A—C12A—C11A	117.5 (4)	C13B—C12B—C11B	118.2 (4)
C13A—C12A—H12A	121.2	C13B—C12B—H12B	120.9
C11A—C12A—H12A	121.2	C11B—C12B—H12B	120.9
C12A—C13A—C14A	124.0 (4)	C14B—C13B—C12B	122.8 (4)
C12A—C13A—N13A	118.5 (4)	C14B—C13B—N13B	119.2 (4)
C14A—C13A—N13A	117.5 (4)	C12B—C13B—N13B	118.0 (4)
C13A—C14A—C15A	117.5 (4)	C15B—C14B—C13B	118.1 (4)
C13A—C14A—H14A	121.2	C15B—C14B—H14B	121.0
C15A—C14A—H14A	121.2	C13B—C14B—H14B	121.0
C16A—C15A—C14A	120.3 (4)	C14B—C15B—C16B	121.3 (4)
C16A—C15A—H15A	119.8	C14B—C15B—H15B	119.4
C14A—C15A—H15A	119.8	C16B—C15B—H15B	119.4
C15A—C16A—C11A	121.0 (4)	C15B—C16B—C11B	119.5 (4)
C15A—C16A—H16A	119.5	C15B—C16B—H16B	120.2
C11A—C16A—H16A	119.5	C11B—C16B—H16B	120.2
O13A—N13A—O14A	124.6 (4)	O14B—N13B—O13B	124.1 (4)
O13A—N13A—C13A	117.1 (4)	O14B—N13B—C13B	118.7 (4)
O14A—N13A—C13A	118.2 (4)	O13B—N13B—C13B	117.1 (4)

C1A—C7A—N1A—C11A	−177.1 (4)	C1B—C7B—N1B—C11B	−179.4 (4)
N1A—C7A—C1A—C2A	0.4 (7)	N1B—C7B—C1B—C2B	1.1 (6)
C7A—N1A—C11A—C12A	−0.1 (7)	C7B—N1B—C11B—C12B	176.9 (4)
C4A—C5A—N5A—O51A	8.2 (6)	C4B—C5B—N5B—O51B	1.2 (7)
C12A—C13A—N13A—O13A	−7.1 (7)	C12B—C13B—N13B—O13B	5.5 (7)
C6A—C1A—C2A—O2A	179.3 (4)	C6B—C1B—C2B—O2B	179.7 (4)
C7A—C1A—C2A—O2A	−1.8 (7)	C7B—C1B—C2B—O2B	−0.3 (6)
C6A—C1A—C2A—C3A	−1.2 (6)	C6B—C1B—C2B—C3B	−0.5 (6)
C7A—C1A—C2A—C3A	177.7 (4)	C7B—C1B—C2B—C3B	179.4 (4)
O2A—C2A—C3A—C4A	179.4 (4)	O2B—C2B—C3B—C4B	−179.9 (4)
C1A—C2A—C3A—C4A	0.0 (6)	C1B—C2B—C3B—C4B	0.4 (7)
O2A—C2A—C3A—I3A	1.9 (6)	O2B—C2B—C3B—I3B	−1.2 (6)
C1A—C2A—C3A—I3A	−177.6 (3)	C1B—C2B—C3B—I3B	179.0 (3)
C2A—C3A—C4A—C5A	1.6 (6)	C2B—C3B—C4B—C5B	0.2 (7)
I3A—C3A—C4A—C5A	179.1 (3)	I3B—C3B—C4B—C5B	−178.4 (3)
C3A—C4A—C5A—C6A	−2.0 (6)	C3B—C4B—C5B—C6B	−0.7 (7)
C3A—C4A—C5A—N5A	177.9 (4)	C3B—C4B—C5B—N5B	−179.6 (4)
C4A—C5A—C6A—C1A	0.8 (6)	C4B—C5B—C6B—C1B	0.6 (7)
N5A—C5A—C6A—C1A	−179.2 (4)	N5B—C5B—C6B—C1B	179.5 (4)
C2A—C1A—C6A—C5A	0.9 (6)	C2B—C1B—C6B—C5B	0.1 (7)
C7A—C1A—C6A—C5A	−178.1 (4)	C7B—C1B—C6B—C5B	−179.9 (4)
C6A—C5A—N5A—O51A	−171.8 (4)	C6B—C5B—N5B—O51B	−177.7 (5)
C6A—C5A—N5A—O52A	8.9 (6)	C6B—C5B—N5B—O52B	3.2 (7)
C4A—C5A—N5A—O52A	−171.1 (4)	C4B—C5B—N5B—O52B	−177.8 (4)
C6A—C1A—C7A—N1A	179.3 (4)	C6B—C1B—C7B—N1B	−179.0 (4)
C7A—N1A—C11A—C16A	177.5 (4)	C7B—N1B—C11B—C16B	−2.5 (7)
C16A—C11A—C12A—C13A	−0.1 (7)	C16B—C11B—C12B—C13B	1.8 (7)
N1A—C11A—C12A—C13A	177.4 (4)	N1B—C11B—C12B—C13B	−177.5 (4)
C11A—C12A—C13A—C14A	−0.7 (7)	C11B—C12B—C13B—C14B	−1.3 (7)
C11A—C12A—C13A—N13A	−179.6 (4)	C11B—C12B—C13B—N13B	179.3 (4)
C12A—C13A—C14A—C15A	0.8 (8)	C12B—C13B—C14B—C15B	−0.1 (7)
N13A—C13A—C14A—C15A	179.7 (5)	N13B—C13B—C14B—C15B	179.3 (4)
C13A—C14A—C15A—C16A	0.0 (8)	C13B—C14B—C15B—C16B	0.9 (7)
C14A—C15A—C16A—C11A	−0.8 (9)	C14B—C15B—C16B—C11B	−0.3 (7)
C12A—C11A—C16A—C15A	0.9 (8)	C12B—C11B—C16B—C15B	−1.1 (7)
N1A—C11A—C16A—C15A	−176.9 (5)	N1B—C11B—C16B—C15B	178.2 (4)
C14A—C13A—N13A—O13A	173.9 (5)	C14B—C13B—N13B—O14B	4.8 (7)
C12A—C13A—N13A—O14A	175.7 (5)	C12B—C13B—N13B—O14B	−175.8 (5)
C14A—C13A—N13A—O14A	−3.3 (7)	C14B—C13B—N13B—O13B	−173.9 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2A—H2A···N1A	0.82	1.85	2.580 (4)	148
O2B—H2B···N1B	0.82	1.81	2.549 (4)	149
C7A—H7A···O52B	0.93	2.37	3.263 (5)	160
C7B—H7B···O52A	0.93	2.36	3.254 (5)	162
C14A—H14A···O51Aⁱ	0.93	2.53	3.372 (6)	151
C14B—H14B···O14Bⁱⁱ	0.93	2.51	3.279 (6)	141
C16A—H16A···O13Bⁱⁱⁱ	0.93	2.47	3.377 (5)	166

Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x, −y, −z+1; (iii) x+3/2, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₈IN₃O₅
M_r	413.12
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	291
a, b, c (Å)	9.2957 (4), 27.5905 (13), 11.0084 (5)
β (°)	93.830 (2)
V (Å³)	2817.1 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	2.30
Crystal size (mm)	0.30 × 0.22 × 0.05

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.545, 0.893
No. of measured, independent and observed [I > 2σ(I)] reflections	29048, 10158, 4201
R_int	0.068
(sin θ/λ)_max (Å⁻¹)	0.757

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.093, 0.87
No. of reflections	10158
No. of parameters	399
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.72, −0.51

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 2000), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97 and PRPKAPPA (Ferguson, 1999).

Selected geometric parameters (Å, º) top

C1A—C2A	1.411 (5)	C1B—C2B	1.419 (5)
C2A—C3A	1.406 (5)	C2B—C3B	1.414 (5)
C3A—C4A	1.377 (5)	C3B—C4B	1.368 (5)
C4A—C5A	1.387 (5)	C4B—C5B	1.388 (5)
C5A—C6A	1.380 (5)	C5B—C6B	1.359 (5)
C6A—C1A	1.394 (5)	C6B—C1B	1.388 (5)
C2A—O2A	1.327 (4)	C2B—O2B	1.311 (4)
C5A—N5A	1.457 (5)	C5B—N5B	1.463 (5)
N5A—O51A	1.217 (4)	N5B—O51B	1.204 (4)
N5A—O52A	1.229 (4)	N5B—O52B	1.232 (4)
C13A—N13A	1.484 (5)	C13B—N13B	1.475 (5)
N13A—O13A	1.198 (5)	N13B—O13B	1.215 (5)
N13A—O14A	1.207 (4)	N13B—O14B	1.208 (4)

C1A—C7A—N1A—C11A	−177.1 (4)	C1B—C7B—N1B—C11B	−179.4 (4)
N1A—C7A—C1A—C2A	0.4 (7)	N1B—C7B—C1B—C2B	1.1 (6)
C7A—N1A—C11A—C12A	−0.1 (7)	C7B—N1B—C11B—C12B	176.9 (4)
C4A—C5A—N5A—O51A	8.2 (6)	C4B—C5B—N5B—O51B	1.2 (7)
C12A—C13A—N13A—O13A	−7.1 (7)	C12B—C13B—N13B—O13B	5.5 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2A—H2A···N1A	0.82	1.85	2.580 (4)	148
O2B—H2B···N1B	0.82	1.81	2.549 (4)	149
C7A—H7A···O52B	0.93	2.37	3.263 (5)	160
C7B—H7B···O52A	0.93	2.36	3.254 (5)	162
C14A—H14A···O51Aⁱ	0.93	2.53	3.372 (6)	151
C14B—H14B···O14Bⁱⁱ	0.93	2.51	3.279 (6)	141
C16A—H16A···O13Bⁱⁱⁱ	0.93	2.47	3.377 (5)	166

Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x, −y, −z+1; (iii) x+3/2, −y+1/2, z−1/2.

Acknowledgements

The authors thank the University of Aberdeen for funding the purchase of the diffractometer. JLW thanks CNPq and FAPERJ for financial support.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bernstein, 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
Bruker (1998). SMART. Version 5.0. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2000). SADABS (Version 2.03) and SAINT (Version 6.02a). Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ferguson, G. (1999). PRPKAPPA. University of Guelph, Canada. Google Scholar
Ferguson, G., Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2005). Acta Cryst. C61, o445–o449. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Garden, S. J., da Cunha, F. R., Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2004). Acta Cryst. C60, o12–o14. Web of Science CSD CrossRef IUCr Journals Google Scholar
Glidewell, C., Howie, R. A., Low, J. N., Skakle, J. M. S., Wardell, S. M. S. V. & Wardell, J. L. (2002). Acta Cryst. B58, 864–876. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Starbuck, J., Norman, N. C. & Orpen, A. G. (1999). New J. Chem. 23, 969–972. Web of Science CrossRef Google Scholar
Wardell, J. L., Wardell, S. M. S. V., Skakle, J. M. S., Low, J. N. & Glidewell, C. (2002). Acta Cryst. C58, o428–o430. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar

© International Union of Crystallography. Prior permission is not required to reproduce short quotations, tables and figures from this article, provided the original authors and source are cited. For more information, click here.

STRUCTURAL
CHEMISTRY

ISSN: 2053-2296

Volume 62| Part 7| July 2006| Pages o441-o443

doi:10.1107/S0108270106020373

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Search term		doi		Advanced search
Author		volume	page

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

N-(2-Hydr­­oxy-3-iodo-5-nitro­benzyl­­idene)-3-nitro­aniline: conformational isomers linked into complex sheets by five C—H⋯O hydrogen bonds and a two-centre iodo–nitro inter­action

Comment

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N-(2-Hydroxy-3-iodo-5-nitrobenzylidene)-3-nitroaniline: conformational isomers linked into complex sheets by five C—H⋯O hydrogen bonds and a two-centre iodo–nitro interaction