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Journal logoSTRUCTURAL
CHEMISTRY
ISSN: 2053-2296

3-Iodo­anilinium 2-carb­­oxy-6-nitro­benzoate: a three-dimensional framework built from O—H⋯O and N—H⋯O hydrogen bonds and a two-centre iodo–nitro inter­action

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

(Received 22 February 2005; accepted 24 February 2005; online 18 March 2005)

In the title compound, C6H7IN+·C8H4NO6, the anions are linked by a single type of O—H⋯O hydrogen bond into C(7) chains, and these chains are linked via three independent N—H⋯O hydrogen bonds into sheets. The sheets, in turn, are linked by a two-centre iodo–nitro inter­action into a single three-dimensional framework.

Comment

We report here the mol­ecular and supramolecular structure of the title compound, (I)[link], and compare it with the isomeric 4-­iodo­anilinium 2-carboxy-6-nitrobenzoate, (II)[link] (Glidewell et al., 2003[Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2003). Acta Cryst. C59, o509-o511.]). Compound (I)[link] is a salt; the H atoms are all fully ordered, and the C—O distances (Table 1[link]) in both the un-ionized carbox­yl group and the anionic carboxyl­ate group are fully consistent with the H-atom locations found from difference maps. Of the three adjacent substituents in the anion, the central carboxyl­ate group is nearly orthogonal to the ring, while the two outer substituents show much smaller rotations about the exocyclic bonds away from planarity, as shown by the key torsion angles (Table 1[link]); these observations can be ascribed to steric congestion.

The supramolecular structure of (I)[link] (Fig. 1[link]) contains hydrogen-bonded sheets, which are linked into a continuous three-dimensional framework structure by a two-centre iodo–nitro inter­action. The formation of the hydrogen-bonded sheet is most readily analysed in terms of the low-dimensional substructures from which it is generated.

The anions are linked by a single O—H⋯O hydrogen bond (Table 2[link]) to form chains running parallel to the [010] direction. Carbox­yl atom O12 in the anion at (x, y, z) acts as a hydrogen-bond donor to carboxyl­ate atom O21 in the anion at (1 − x, [{1\over 2}] + y, [{3\over 2}] − z), so forming a C(7) chain (Bernstein et al., 1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]) of anions generated by the 21 screw axis along ([{1\over 2}], y, [{3\over 4}]) (Fig. 2[link]). A second anion chain, antiparallel to the first and related to it by inversion, is generated by the 21 screw axis along ([{1\over 2}], −y, [{1\over 4}]), and these chains are linked by N—H⋯O hydrogen bonds into (100) sheets.

[Scheme 1]

Anilinium atom N41 acts as a hydrogen-bond donor, via H41A, to carboxyl­ate atom O22 within the asymmetric unit (Fig. 3[link]); in addition, atom N41 in the cation at (x, y, z) acts as a donor, via H41B, to carboxyl­ate atom O21 in the anion at (x, [{3\over 2}] − y, −[{1\over 2}] + z). Propagation of these two N—H⋯O hydrogen bonds then produces a C22(6) chain running parallel to the [001] direction and generated by the c-glide plane at y = [3\over 4] (Fig. 3[link]). Since the anions at (x, y, z) and (x, [{3\over 2}] − y, −[{1\over 2}] + z) form parts, respectively, of the anion chains along ([{1\over 2}], y, [{3\over 4}]) and ([{1\over 2}], −y, [{1\over 4}]), these three hydrogen bonds, one O—H⋯O and two N—H⋯O, suffice to form a (100) sheet. In the third N—H⋯O hydrogen bond, atom N41 in the cation at (x, y, z) acts as a donor, via H41C, to carboxyl­ate atom O22 in the anion at (1 − x, 1 − y, 1 − z), so generating a centrosymmetric R42(8) ring (Fig. 4[link]), which serves further to reinforce the sheet. It is notable that the O atoms of the nitro group play no part in the hydrogen bonding.

Just a single (100) sheet passes through each unit cell and it is tripartite in form, with a central polar layer containing the hydrogen bonds linking the –NH3+, –COO and –COOH units, and with two outer layers containing the iodo­phen­yl and nitro­phen­yl units. The location of both the iodo and the nitro substituents on the outer faces of this tripartite layer allows the formation of iodo–nitro inter­actions, which link adjacent sheets.

Atom I43 in the cation at (x, y, z) lies in the (100) sheet centred at x = [{1\over 2}]; this atom forms a two-centre iodo–nitro inter­action with nitro atom O32 in the anion at (−x, [{1\over 2}] + y, [{1\over 2}] − z) [I⋯Oiv = 3.423 (4) Å, C—I⋯Oiv = 166.1 (2)° and I⋯Oiv—Niv = 141.4 (3)°; symmetry code: (iv) −x, [{1\over 2}] + y, [{1\over 2}] − z], so producing a C22(12) chain (Bernstein et al., 1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]; Starbuck et al., 1999[Starbuck, J., Norman, N. C. & Orpen, A. G. (1999). New J. Chem. 23, 969-972.]) running parallel to the [010] direction (Fig. 5[link]). The anion at (−x, [{1\over 2}] + y, [{1\over 2}] − z) forms part of the (100) sheet centred at x = −[{1\over 2}], and propagation by inversion of this iodo–nitro inter­action thus links each sheet to the two adjacent sheets, hence forming a single three-dimensional framework structure.

The only possible ππ stacking inter­action in the structure of (I)[link] is, at best, a weak one and, in any event, it lies within the hydrogen-bonded sheet. The ar­yl rings of the anion at (x, y, z) and the cation at (x, [\,\,{3\over 2}] − y, [{1\over 2}] + z) have a ring-centroid separation of 3.760 (2) Å; in addition, the dihedral angle between the ring planes is 8.4 (2)° and the inter­planar spacing is ca 3.65 Å, corresponding to a centroid offset of ca 0.88 Å.

The supramolecular structure of (I)[link] may be compared with that of its isomer (II)[link]. In (II)[link], the anions again form C(7) chains generated by a 21 screw axis, but the linking of these chains by the cations into sheets differs in detail from that in (I)[link]; in particular, there are no centrosymmetric motifs in (II)[link]. Moreover, there are no iodo–nitro inter­actions in (II)[link] and no significant direction-specific inter­actions between adjacent hydrogen-bonded sheets.

[Figure 1]
Figure 1
The independent components of (I)[link], showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2]
Figure 2
Part of the crystal structure of (I)[link], showing the formation of a hydrogen-bonded C(7) chain of anions along [010]. For clarity, H atoms bonded to C atoms have been omitted. Atoms marked with an asterisk (*), a hash (#) or a dollar sign ($) are at the symmetry positions (1 − x, [{1\over 2}] + y, [{3\over 2}] − z), (x, −1 + y, z) and (1 − x, −[{1\over 2}] + y, [3\over2] − z), respectively.
[Figure 3]
Figure 3
A stereoview of part of the crystal structure of (I)[link], showing the formation of a hydrogen-bonded C22(6) chain along [001]. For clarity, H atoms bonded to C atoms have been omitted.
[Figure 4]
Figure 4
Part of the crystal structure of (I)[link], showing the formation of a hydrogen-bonded R42(8) ring. For clarity, H atoms bonded to C atoms have been omitted. Atoms marked with an asterisk (*) are at the symmetry position (1 − x, 1 − y, 1 − z).
[Figure 5]
Figure 5
A stereoview of part of the crystal structure of (I)[link], showing the [010] chain generated by the iodo–nitro inter­action. For clarity, H atoms bonded to C atoms have been omitted.

Experimental

A mixture of 3-iodo­aniline and 3-nitro­phthalic acid (5 mmol of each) in methanol (20 ml) was heated under reflux for 30 min and then cooled. The solid that formed slowly was collected and recrystallized from acetone (m.p. 460–461 K).

Crystal data
  • C6H7IN+·C8H4NO[{}_{6}^{- }]

  • Mr = 430.15

  • Monoclinic, P 21 /c

  • a = 16.0068 (10) Å

  • b = 7.8616 (5) Å

  • c = 13.5718 (9) Å

  • β = 113.3770 (10)°

  • V = 1567.67 (17) Å3

  • Z = 4

  • Dx = 1.823 Mg m−3

  • Mo Kα radiation

  • Cell parameters from 3603 reflections

  • θ = 2.8–27.5°

  • μ = 2.08 mm−1

  • T = 291 (2) K

  • Plate, colourless

  • 0.50 × 0.10 × 0.08 mm

Data collection
  • Bruker SMART 1000 CCD area-detector diffractometer

  • φω scans

  • Absorption correction: multi-scan(SADABS; Bruker, 2000[Bruker (2000). SADABS (Version 2.03) and SAINT (Version 6.02a). Bruker AXS Inc., Madison, Wisconsin, USA.])Tmin = 0.424, Tmax = 0.852

  • 11 173 measured reflections

  • 3603 independent reflections

  • 2253 reflections with I > 2σ(I)

  • Rint = 0.037

  • θmax = 27.5°

  • h = −13 → 20

  • k = −10 → 10

  • l = −17 → 17

Refinement
  • Refinement on F2

  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.113

  • S = 0.95

  • 3603 reflections

  • 210 parameters

  • H-atom parameters constrained

  • w = 1/[σ2(Fo2) + (0.0656P)2] where P = (Fo2 + 2Fc2)/3

  • (Δ/σ)max < 0.001

  • Δρmax = 0.89 e Å−3

  • Δρmin = −0.95 e Å−3

Table 1
Selected geometric parameters (Å, °)[link]

C11—O11 1.214 (4)
C11—O12 1.302 (4)
C21—O21 1.253 (4)
C21—O22 1.245 (4)
C2—C1—C11—O11 157.3 (4)
C1—C2—C21—O21 104.2 (4)
C2—C3—N31—O31 −13.4 (5)

Table 2
Hydrogen-bond geometry (Å, °)[link]

D—H⋯A D—H H⋯A DA D—H⋯A
O12—H12⋯O21i 0.82 1.75 2.570 (3) 176
N41—H41A⋯O22 0.89 1.88 2.745 (4) 164
N41—H41B⋯O21ii 0.89 2.23 3.052 (4) 153
N41—H41C⋯O22iii 0.89 1.91 2.747 (4) 156
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (iii) -x+1, -y+1, -z+1.

For compound (I)[link], the space group P21/c was uniquely assigned from the systematic absences. All H atoms were located from difference maps and then treated as riding atoms [C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C,N) or 1.5Ueq(O)].

Data collection: SMART (Bruker, 1998[Bruker (1998). SMART. Version 5.0. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SADABS (Version 2.03) and SAINT (Version 6.02a). Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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


Comment top

We report here the molecular and supramolecular structure of the title compound, (I), and compare it with the isomeric 4-iodoanilinium 3-nitro(hydrogenphthalate) (II) (Glidewell et al., 2003). Compound (I) is a salt; the H atoms are all fully ordered, and the C—O distances (Table 1) in both the un-ionized carboxyl group and the anionic carboxylate group are fully consistent with the H atom locations found from difference maps. Of the three adjacent substituents in the anion, the central carboxylate group is nearly orthogonal to the ring, while the two outer substituents show much smaller rotations about the exocyclic bonds away from planarity, as shown by the key torsion angles; these observations can be ascribed to steric congestion.

The supramolecular structure of (I) (Fig. 1) contains hydrogen-bonded sheets, which are linked into a continuous three-dimensional framework structure by a two-centre iodo–nitro interaction. The formation of the hydrogen-bonded sheet is most readily analysed in terms of the low-dimensional substructures from which it is generated.

The anions are linked by a single O—H···O hydrogen bond (Table 2) to form chains running parallel to the [010] direction. Carboxyl atom O12 in the anion at (x, y, z) acts as a hydrogen-bond donor to carboxylate atom O21 in the anion at (1 − x, 1/2 + y, 3/2 − z), so forming a C(7) chain (Bernstein et al., 1995) of anions generated by the 21 screw axis along (1/2, y, 3/4) (Fig. 2). A second anion chain, anti-parallel to the first and related to it by inversion, is generated by the 21 screw axis along (1/2, −y, 1/4), and these chains are linked by N—H···O hydrogen bonds into (100) sheets.

Anilinium atom N41 acts as a hydrogen-bond donor, via H41A, to carboxylate atom O22 within the asymmetric unit (Fig. 3); in addition, atom N41 in the cation at (x, y, z) acts as a donor, via H41B, to carboxylate atom O21 in the anion at (x, 3/2 − y, −1/2 + z). Propagation of these two N—H···O hydrogen bonds then produces a C22(6) chain running parallel to the [001] direction and generated by the c-glide plane at y = 0.75 (Fig. 3). Since the anions at (x, y, z) and (x, 3/2 − y, −1/2 + z) form parts, respectively, of the anion chains along (1/2, y, 3/4) and (1/2, −y, 1/4), these three hydrogen bonds, one of O—H···O type and two of N—H···O type, suffice to form a (100) sheet. In the third N—H···O hydrogen bond, atom N41 in the cation at (x, y, z) acts as a donor, via H41C, to carboxylate atom O22 in the anion at (1 − x, 1 − y, 1 − z), so generating a centrosymmetric R24(8) ring (Fig. 4), which serves further to reinforce the sheet. It is notable that the O atoms of the nitro group play no part in the hydrogen bonding.

Just a single (100) sheet passes through each unit cell and it is tripartite in form, with a central polar layer containing the hydrogen bonds linking the –NH3+, –COO and –COOH units, and with two outer layers containing the iodophenyl and nitrophenyl units. The location of both the iodo and the nitro substituents on the outer faces of this tripartite layer allows the formation of iodo–nitro interactions, which link adjacent sheets

Atom I43 in the cation at (x, y, z) lies in the (100) sheet centred at x = 1/2; this atom forms a two-centre iodo–nitro interaction with nitro atom O32 in the anion at (−x, 1/2 + y, 1/2 − z) [I···Oi = 3.423 (4) Å, C—I···Oi = 166.1 (2)° and I···Oi—Ni = 141.4 (3)°; symmetry code: (i) −x, 1/2 + y, 1/2 − z], so producing a C22(12) chain (Bernstein et al., 1995; Starbuck et al., 1999) running parallel to the [010] direction (Fig. 5). The anion at (−x, 1/2 + y, 1/2 − z) forms part of the (100) sheet centred at x = −1/2, and propagation by inversion of this iodo–nitro interaction thus links each sheet to the two adjacent sheets, hence forming a single three-dimensional framework structure.

The only possible ππ stacking interaction in the structure of (I) is, at best, a weak one and, in any event, it lies within the hydrogen-bonded sheet. The aryl rings of the anion at (x, y, z) and the cation at (x, 3/2 − y, 1/2 + z) have a ring-centroid separation of 3.760 (2) Å; the dihedral angle between the ring planes is 8.4 (2)° and the interplanar spacing is ca 3.65 Å, corresponding to a centroid offset of ca 0.88 Å.

The supramolecular structure of (I) may be compared with that of its isomer (II). In (II), the anions again form C(7) chains generated by a 21 screw axes, but the linking of these chains by the cations into sheets differs in detail from that in (I); in particular there are no centrosymmetric motifs in (II). Moreover, there are no iodo–.nitro interactions in (II) and no significant direction-specific interactions between adjacent hydrogen-bonded sheets.

Experimental top

A mixture of 3-iodoaniline and 3-nitrophthalic acid (5 mmol of each) in methanol (20 ml) was heated under reflux for 30 min and then cooled. The solid that formed slowly was collected and recrystallized from acetone (m.p. 460–461 K).

Refinement top

For compound (I), the space group P21/c was uniquely assigned from the systematic absences. All H atoms were located from difference maps and then treated as riding atoms [C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C,N) or 1.5Ueq(O)].

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
[Figure 1] Fig. 1. The independent components of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. Part of the crystal structure of (I), showing the formation of a hydrogen-bonded C(7) chain of anions along [010]. For clarity, H atoms bonded to C atoms have been omitted. Atoms marked with an asterisk (*), a hash (#) or a dollar sign ($) are at the symmetry positions (1 − x, 1/2 + y, 3/2 − z), (x, −1 + y, z) and (1 − x, −1/2 + y, 1.5 − z), respectively.
[Figure 3] Fig. 3. A stereoview of part of the crystal structure of (I), showing the formation of a hydrogen-bonded C22(6) chain along [001]. For clarity, H atoms bonded to C atoms have been omitted.
[Figure 4] Fig. 4. Part of the crystal structure of (I), showing the formation of a hydrogen-bonded R24(8) ring For clarity, H atoms bonded to C atoms have been omitted. Atoms marked with an asterisk are at the symmetry position (1 − x, 1 − y, 1 − z).
[Figure 5] Fig. 5. A stereoview of part of the crystal structure of (I), showing the [010] chain generated by the iodo–nitro interaction. For clarity, H atoms bonded to C atoms have been omitted.
3-Iodoanilinium 2-carboxy-6-nitrobenzoate top
Crystal data top
C6H7IN+·C8H4NO6F(000) = 840
Mr = 430.15Dx = 1.823 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3603 reflections
a = 16.0068 (10) Åθ = 2.8–27.5°
b = 7.8616 (5) ŵ = 2.08 mm1
c = 13.5718 (9) ÅT = 291 K
β = 113.377 (1)°Plate, colourless
V = 1567.67 (17) Å30.50 × 0.10 × 0.08 mm
Z = 4
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
3603 independent reflections
Radiation source: fine-focus sealed X-ray tube2253 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
ϕω scansθmax = 27.5°, θmin = 2.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 1320
Tmin = 0.424, Tmax = 0.852k = 1010
11173 measured reflectionsl = 1717
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113H-atom parameters constrained
S = 0.95 w = 1/[σ2(Fo2) + (0.0656P)2]
where P = (Fo2 + 2Fc2)/3
3603 reflections(Δ/σ)max < 0.001
210 parametersΔρmax = 0.89 e Å3
0 restraintsΔρmin = 0.95 e Å3
Crystal data top
C6H7IN+·C8H4NO6V = 1567.67 (17) Å3
Mr = 430.15Z = 4
Monoclinic, P21/cMo Kα radiation
a = 16.0068 (10) ŵ = 2.08 mm1
b = 7.8616 (5) ÅT = 291 K
c = 13.5718 (9) Å0.50 × 0.10 × 0.08 mm
β = 113.377 (1)°
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
3603 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
2253 reflections with I > 2σ(I)
Tmin = 0.424, Tmax = 0.852Rint = 0.037
11173 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.113H-atom parameters constrained
S = 0.95Δρmax = 0.89 e Å3
3603 reflectionsΔρmin = 0.95 e Å3
210 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O110.4599 (2)1.1267 (4)0.5676 (2)0.0730 (10)
O120.47858 (18)0.9237 (3)0.68785 (18)0.0444 (6)
O210.37966 (16)0.5996 (3)0.70209 (17)0.0382 (5)
O220.43485 (16)0.5855 (3)0.57526 (18)0.0383 (5)
O310.2429 (2)0.4413 (4)0.5109 (3)0.0745 (10)
O320.1067 (2)0.5267 (5)0.4370 (4)0.1004 (14)
N310.1878 (2)0.5516 (4)0.4787 (3)0.0470 (8)
C10.3376 (2)0.9371 (4)0.5372 (3)0.0336 (7)
C20.3109 (2)0.7683 (4)0.5447 (2)0.0287 (7)
C30.2203 (2)0.7291 (4)0.4839 (3)0.0347 (8)
C40.1571 (3)0.8466 (5)0.4206 (3)0.0485 (10)
C50.1859 (3)1.0100 (5)0.4148 (3)0.0528 (10)
C60.2757 (3)1.0524 (5)0.4719 (3)0.0483 (10)
C110.4318 (3)1.0030 (5)0.5986 (3)0.0408 (8)
C210.3805 (2)0.6391 (4)0.6130 (2)0.0298 (7)
I430.04980 (2)0.70440 (6)0.12973 (2)0.07919 (18)
N410.41182 (18)0.6134 (4)0.3645 (2)0.0353 (6)
C410.3258 (2)0.5310 (4)0.2994 (2)0.0349 (8)
C420.2487 (2)0.6300 (5)0.2550 (3)0.0394 (8)
C430.1665 (3)0.5514 (6)0.1956 (3)0.0522 (11)
C440.1623 (3)0.3772 (7)0.1795 (3)0.0664 (13)
C450.2406 (4)0.2826 (6)0.2226 (4)0.0673 (14)
C460.3238 (3)0.3574 (5)0.2847 (3)0.0494 (10)
H40.09660.81570.38290.058*
H50.14491.09100.37270.063*
H60.29501.16220.46620.058*
H120.52230.98220.72450.067*
H41A0.41600.62470.43150.053*
H41B0.41400.71560.33740.053*
H41C0.45790.55020.36420.053*
H420.25170.74720.26490.047*
H440.10700.32480.13990.080*
H450.23810.16600.21020.081*
H460.37640.29220.31520.059*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O110.077 (2)0.0629 (19)0.0600 (17)0.0317 (18)0.0076 (17)0.0165 (15)
O120.0442 (15)0.0454 (15)0.0342 (12)0.0125 (11)0.0055 (12)0.0010 (11)
O210.0377 (13)0.0448 (14)0.0312 (11)0.0087 (11)0.0127 (10)0.0082 (10)
O220.0368 (13)0.0457 (14)0.0343 (11)0.0117 (11)0.0161 (11)0.0026 (10)
O310.061 (2)0.0398 (17)0.100 (2)0.0042 (15)0.0079 (19)0.0005 (16)
O320.043 (2)0.078 (2)0.159 (4)0.0221 (17)0.019 (2)0.006 (2)
N310.0415 (19)0.048 (2)0.0468 (17)0.0071 (16)0.0126 (16)0.0063 (15)
C10.0390 (18)0.0316 (19)0.0304 (15)0.0013 (15)0.0139 (15)0.0001 (13)
C20.0313 (17)0.0326 (18)0.0227 (14)0.0062 (13)0.0113 (13)0.0000 (12)
C30.0320 (17)0.040 (2)0.0299 (15)0.0007 (15)0.0096 (14)0.0027 (14)
C40.0324 (19)0.065 (3)0.042 (2)0.0108 (18)0.0081 (17)0.0004 (18)
C50.051 (2)0.051 (2)0.051 (2)0.024 (2)0.015 (2)0.0166 (19)
C60.060 (3)0.032 (2)0.053 (2)0.0092 (18)0.023 (2)0.0083 (17)
C110.049 (2)0.036 (2)0.0370 (18)0.0059 (17)0.0170 (17)0.0057 (15)
C210.0285 (16)0.0279 (17)0.0292 (15)0.0015 (13)0.0075 (14)0.0018 (13)
I430.03459 (18)0.1417 (4)0.0517 (2)0.01097 (17)0.00697 (14)0.00028 (18)
N410.0317 (14)0.0395 (16)0.0351 (14)0.0021 (13)0.0138 (12)0.0012 (12)
C410.0327 (17)0.044 (2)0.0285 (15)0.0014 (15)0.0130 (14)0.0008 (14)
C420.0360 (18)0.053 (2)0.0304 (16)0.0004 (17)0.0142 (15)0.0021 (15)
C430.037 (2)0.083 (3)0.0337 (18)0.008 (2)0.0108 (17)0.0003 (19)
C440.059 (3)0.085 (4)0.045 (2)0.029 (3)0.010 (2)0.014 (2)
C450.086 (4)0.053 (3)0.056 (3)0.020 (3)0.021 (3)0.008 (2)
C460.062 (3)0.040 (2)0.044 (2)0.0012 (19)0.019 (2)0.0014 (17)
Geometric parameters (Å, º) top
C1—C61.376 (5)C5—H50.93
C1—C21.410 (5)C6—H60.93
C1—C111.496 (5)C41—C461.378 (5)
C11—O111.214 (4)C41—C421.380 (5)
C11—O121.302 (4)C41—N411.459 (4)
O12—H120.82N41—H41A0.89
C2—C31.388 (5)N41—H41B0.89
C2—C211.522 (4)N41—H41C0.89
C21—O211.253 (4)C42—C431.386 (5)
C21—O221.245 (4)C42—H420.93
C3—C41.388 (5)C43—C441.384 (7)
C3—N311.481 (5)C43—I432.099 (4)
N31—O311.190 (4)C44—C451.373 (7)
N31—O321.209 (4)C44—H440.93
C4—C51.377 (6)C45—C461.392 (7)
C4—H40.93C45—H450.93
C5—C61.376 (6)C46—H460.93
C6—C1—C2120.3 (3)C1—C6—H6119.1
C6—C1—C11116.1 (3)C5—C6—H6119.1
C2—C1—C11123.6 (3)C46—C41—C42122.0 (3)
O11—C11—O12123.4 (4)C46—C41—N41119.3 (3)
O11—C11—C1120.9 (3)C42—C41—N41118.7 (3)
O12—C11—C1115.6 (3)C41—N41—H41A109.5
C11—O12—H12109.5C41—N41—H41B109.5
C3—C2—C1116.2 (3)H41A—N41—H41B109.5
C3—C2—C21123.6 (3)C41—N41—H41C109.5
C1—C2—C21120.1 (3)H41A—N41—H41C109.5
O22—C21—O21126.2 (3)H41B—N41—H41C109.5
O22—C21—C2115.9 (3)C41—C42—C43118.8 (4)
O21—C21—C2117.9 (3)C41—C42—H42120.6
C4—C3—C2123.6 (3)C43—C42—H42120.6
C4—C3—N31116.2 (3)C44—C43—C42120.5 (4)
C2—C3—N31120.1 (3)C44—C43—I43121.4 (3)
O31—N31—O32123.8 (4)C42—C43—I43118.1 (3)
O31—N31—C3118.2 (3)C45—C44—C43119.3 (4)
O32—N31—C3117.8 (3)C45—C44—H44120.3
C5—C4—C3118.5 (4)C43—C44—H44120.3
C5—C4—H4120.7C44—C45—C46121.4 (4)
C3—C4—H4120.7C44—C45—H45119.3
C6—C5—C4119.5 (3)C46—C45—H45119.3
C6—C5—H5120.2C41—C46—C45117.9 (4)
C4—C5—H5120.2C41—C46—H46121.1
C1—C6—C5121.8 (4)C45—C46—H46121.1
C6—C1—C11—O1123.6 (5)C4—C3—N31—O3213.3 (5)
C2—C1—C11—O11157.3 (4)C2—C3—N31—O32170.3 (4)
C6—C1—C11—O12153.6 (3)C2—C3—C4—C52.1 (6)
C2—C1—C11—O1225.5 (5)N31—C3—C4—C5174.2 (3)
C6—C1—C2—C30.4 (5)C3—C4—C5—C60.3 (6)
C11—C1—C2—C3178.7 (3)C2—C1—C6—C52.0 (6)
C6—C1—C2—C21177.3 (3)C11—C1—C6—C5177.1 (4)
C11—C1—C2—C213.7 (5)C4—C5—C6—C11.7 (6)
C3—C2—C21—O22103.3 (4)C46—C41—C42—C431.2 (5)
C1—C2—C21—O2274.1 (4)N41—C41—C42—C43178.3 (3)
C3—C2—C21—O2178.3 (4)C41—C42—C43—C441.1 (5)
C1—C2—C21—O21104.2 (4)C41—C42—C43—I43179.6 (2)
C1—C2—C3—C41.7 (5)C42—C43—C44—C450.3 (6)
C21—C2—C3—C4179.2 (3)I43—C43—C44—C45178.9 (3)
C1—C2—C3—N31174.4 (3)C43—C44—C45—C461.8 (7)
C21—C2—C3—N313.1 (5)C42—C41—C46—C450.2 (6)
C4—C3—N31—O31163.0 (4)N41—C41—C46—C45179.7 (3)
C2—C3—N31—O3113.4 (5)C44—C45—C46—C411.7 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O12—H12···O21i0.821.752.570 (3)176
N41—H41A···O220.891.882.745 (4)164
N41—H41B···O21ii0.892.233.052 (4)153
N41—H41C···O22iii0.891.912.747 (4)156
Symmetry codes: (i) x+1, y+1/2, z+3/2; (ii) x, y+3/2, z1/2; (iii) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC6H7IN+·C8H4NO6
Mr430.15
Crystal system, space groupMonoclinic, P21/c
Temperature (K)291
a, b, c (Å)16.0068 (10), 7.8616 (5), 13.5718 (9)
β (°) 113.377 (1)
V3)1567.67 (17)
Z4
Radiation typeMo Kα
µ (mm1)2.08
Crystal size (mm)0.50 × 0.10 × 0.08
Data collection
DiffractometerBruker SMART 1000 CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.424, 0.852
No. of measured, independent and
observed [I > 2σ(I)] reflections
11173, 3603, 2253
Rint0.037
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.113, 0.95
No. of reflections3603
No. of parameters210
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.89, 0.95

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
C11—O111.214 (4)C21—O211.253 (4)
C11—O121.302 (4)C21—O221.245 (4)
C2—C1—C11—O11157.3 (4)C2—C3—N31—O3113.4 (5)
C1—C2—C21—O21104.2 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O12—H12···O21i0.821.752.570 (3)176
N41—H41A···O220.891.882.745 (4)164
N41—H41B···O21ii0.892.233.052 (4)153
N41—H41C···O22iii0.891.912.747 (4)156
Symmetry codes: (i) x+1, y+1/2, z+3/2; (ii) x, y+3/2, z1/2; (iii) x+1, y+1, z+1.
 

Acknowledgements

X-ray data were collected at the University of Aberdeen; the University is thanked for funding the purchase of the Bruker SMART diffractometer. JNL thanks NCR Self-Service, Dundee, for grants which have provided computing facilities for this work. 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 citationBruker (1998). SMART. Version 5.0. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationBruker (2000). SADABS (Version 2.03) and SAINT (Version 6.02a). Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFerguson, G. (1999). PRPKAPPA. University of Guelph, Canada.  Google Scholar
First citationGlidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2003). Acta Cryst. C59, o509–o511.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationSheldrick, G. M. (1997). SHELXS97 and SHELXL97. 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
First citationStarbuck, J., Norman, N. C. & Orpen, A. G. (1999). New J. Chem. 23, 969–972.  Web of Science CrossRef Google Scholar

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