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In 2,6-di­iodo-4-nitro­phenol, C6H3I2NO3, the mol­ecules are linked, by an O-H...O hydrogen bond and two iodo-nitro interactions, into sheets, which are further linked into a three-dimensional framework by aromatic [pi]-[pi]-stacking interactions. The mol­ecules of 2,6-di­iodo-4-nitro­phenyl acetate, C8H5I2NO4, lie across a mirror plane in space group Pnma, with the acetyl group on the mirror, and they are linked by a single iodo-nitro interaction to form isolated sheets. The mol­ecules of 2,6-di­iodo-4-nitro­anisole, C7H5I2NO3, are linked into isolated chains by a single two-centre iodo-nitro interaction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270102010776/tr1033sup1.cif
Contains datablocks global, I, II, III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270102010776/tr1033Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270102010776/tr1033IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270102010776/tr1033IIIsup4.hkl
Contains datablock III

CCDC references: 193419; 193420; 193421

Comment top

We have recently reported the molecular and supramolecular structures of several iodo-nitro anilines, unsubstituted at N (Garden et al., 2002). In these compounds, the supramolecular aggregation is dominated by a combination of N—H···O hydrogen bonds, iodo···nitro interactions and aromatic π···π stacking interactions, to give either two-dimensional or three-dimensional structures. The title compounds, 2,6-diiodo-4-nitrophenol, (I), 2,6-diiodo-4-nitrophenyl acetate, (II), and 2,6-diiodo-4-nitroanisole, (III), have been designed to reduce the scope for formation of hard (Braga et al., 1995) hydrogen bonds, while retaining the other potential intermolecular interactions, in that (I) has an OH group in place of the NH2 group in simple anilines, allowing the molecule to act as only a single donor in such bonds, while (II) and (III) have no scope at all for the formation of hard hydrogen bonds. \sch

In compound (I) (Fig. 1), a combination of O—H···O hydrogen bonds and two independent iodo···nitro interactions links the molecules into sheets, and these sheets are weakly linked by aromatic π···π stacking interactions to form a continuous three-dimensional structure. The phenolic atom O1 acts as a hydrogen-bond donor to nitro atom O41 at (1 + x, y - 1, z) (Table 2), so generating by translation a C(8) chain (Bernstein et al., 1995) running parallel to the [110] direction. Chains of this type are linked into sheets by the iodo···nitro interactions, which involve both I atoms and both nitro O atoms. Atoms I2 and I6 participate in iodo···nitro interactions with nitro atoms O42 and O41, respectively [I2···O42i 3.326 (4) Å and C2—I2···O42i 152.2 (2)°, and I6···O41ii 3.552 (4) Å and C6—I6···O41ii 157.9 (2)°; symmetry codes: (i) 1 - x, 1 - y, -z; (ii) -x, 1 - y, 2 - z], so generating centrosymmetric R22(12) rings centred at (1/2,0,0) and (0,0,1), respectively. The combination of these two motifs generates a chain of fused rings running parallel to the [102] direction, while the combination of this chain with the hydrogen-bonded chain along [110] generates a (221) sheet in which there are four distinct types of ring, all centrosymmetric (Fig. 2).

The aromatic ring of (I) forms a close π···π contact with that at (1 - x, 1 - y, 1 - z) (Fig. 3); the interplanar spacing between parallel rings is 3.379 (4) Å, the centroid separation is 3.493 (4) Å and the centroid offset is 0.886 (4) Å. In this manner, each (221) sheet (Fig. 2) is linked to the two adjacent sheets, so generating a continuous framework in three dimensions.

Molecules of compound (II) lie across the mirror planes in space group Pnma (Fig. 4). The non-H atoms of the acetate group all lie on the mirror plane (chosen for the sake of convenience as that at y = 1/4 for the reference molecule), so that the plane of the acetate group is orthogonal to the aromatic ring. The methyl group was modelled using six H-atom sites, each with occupancy 0.5. The crystal structure exhibits neither C—H···O hydrogen bonds nor aromatic π···π stacking interactions. Instead, the single short iodo···nitro interaction generates a simple and elegant sheet structure (Fig. 5).

Each of the two symmetry-related I atoms in (II) participates in a two-centre iodo···nitro interaction with the O4 atoms at (1/2 - x, 1 - y, z - 1/2) and at (1/2 - x, y - 1/2, z - 1/2), respectively, with I2···O4 3.323 (3) Å and C—I···O4 140.8 (2)°. Propagation of these interactions produces two C(6) chain motifs running parallel to the [001] direction and generated by the 21 screw axes along (1/4,1/2,z) and (1/4,0,z). The combination of these two symmetry-related motifs and their propagation by the space group generates a (100) sheet in the form of a (4,4) net (Batten & Robson, 1998) built from a single type of R44(20) ring. The central space in each ring is occupied by an acetate group.

In compound (III) (Fig. 6), neither C—H···O hydrogen bonds nor aromatic π···π stacking interactions are present in the crystal structure. The molecules are linked into chains by an iodo···nitro interaction involving only one of the two I atoms and only one of the nitro O atoms. Atom I2 in the molecule at (x,y,z) forms a very short I···O contact with nitro atom O42 in the molecule at (1/2 + x, 1/2 - y, z - 1/2) [I2···O42iv 2.992 (3) Å and C2—I2···O42iv 171.3 (2)°; symmetry code: (iv) 1/2 + x, 1/2 - y, z - 1/2], and propagation of this interaction leads to the formation of a chain running parallel to the [101] direction, generated by the n glide plane at y = 1/4 (Fig. 7).

The intermolecular distances and angles in (I)-(III) present no unusual features. In each compound, the nitro group is almost coplanar with the adjacent aryl ring (Tables 1, 3 and 4).

Experimental top

Compound (I) was obtained by reaction of 4-nitrophenol with K[ICl2] in aqueous solution (Garden et al., 2001). Compounds (II) and (III) were obtained from (I) by acetylation using acetic anhydride, and methylation using dimethylsulfate, respectively. Crystals of (I)-(III) suitable for single-crystal X-ray diffraction were grown by slow evaporation of solutions in ethanol [m.p. 439–441 K for (I), 409–411 K for (II) and 418–419 K for (III)].

Refinement top

Compound (I) is triclinic; space group P1 was selected and confirmed by the analysis. For compound (II), the systematic absences permitted Pnma and Pn21a (= Pna21) as possible space groups; Pnma was selected and confirmed by the structure analysis. For compound (III), the systematic absences permitted C2/c and Cc as possible space groups; C2/c was selected and confirmed by the analysis. All H atoms were located from difference maps and were treated as riding atoms, with O—H distances of 0.84 Å and C—H distances of 0.93–0.98 Å.

Computing details top

Data collection: KappaCCD Server Software (Nonius, 1997) for (I), (III); SMART (Bruker, 1999) for (II). Cell refinement: DENZO-SMN (Otwinowski & Minor, 1997) for (I), (III); SAINT (Bruker, 1999) for (II). Data reduction: DENZO-SMN for (I), (III); SAINT for (II). For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2002); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

Figures top
[Figure 1] Fig. 1. The molecule of (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.
[Figure 2] Fig. 2. Part of the crystal structure of (I), showing formation of a (110) sheet containing four distinct centrosymmetric rings. For the sake of clarity, H atoms bonded to C atoms have been omitted. The atoms marked with an asterisk (*), hash (#), dollar sign (add) or ampersand (add) are at the symmetry positions (1 + x, y - 1, z), (1 - x, 1 - y, -z), (-x, 1 - y, 2 - z) and (x - 1, 1 + y, z), respectively.
[Figure 3] Fig. 3. Part of the crystal structure of (I), showing the π···π stacking interaction. The atoms marked with an asterisk (*) are at the symmetry position (1 - x, 1 - y, 1 - z).
[Figure 4] Fig. 4. The molecule of (II) 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. Atoms with the suffix A are at the symmetry position (x, 1 - y, z). For the sake of clarity, only one set of H atoms bonded to C12 is shown.
[Figure 5] Fig. 5. Part of the crystal structure of (II), showing formation of a (100) sheet of R44(20) rings. For the sake of clarity, H atoms bonded to C atoms have been omitted. The atoms marked with a plus sign (+), asterisk (*), hash (#), dollar sign (add) or ampersand (add) are at the symmetry positions (x, 1/2 - y, z), (1/2 - x, 1 - y, z - 1/2), (1/2 - x, y - 1/2, z - 1/2), (1/2 - x, y - 1/2, 1/2 + z) and (1/2 - x, 1 - y, 1/2 + z), respectively.
[Figure 6] Fig. 6. The molecule of (III) 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.
[Figure 7] Fig. 7. Part of the crystal structure of (III), showing formation of a chain along [101]. Atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (x - 1/2, 1/2 - y, 1/2 + z) and (1/2 + x, 1/2 - y, z - 1/2), respectively.
(I) 2,6-Diiodo-4-nitrophenol top
Crystal data top
C6H3I2NO3Z = 2
Mr = 390.89F(000) = 352
Triclinic, P1Dx = 3.001 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.9749 (2) ÅCell parameters from 1850 reflections
b = 8.0952 (3) Åθ = 2.9–27.4°
c = 8.1395 (3) ŵ = 7.24 mm1
α = 69.3082 (18)°T = 120 K
β = 66.657 (2)°Block, yellow
γ = 67.3547 (15)°0.15 × 0.10 × 0.05 mm
V = 432.59 (3) Å3
Data collection top
Nonius KappaCCD
diffractometer
1850 independent reflections
Radiation source: fine-focus sealed X-ray tube1735 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.091
ϕ scans, and ω scans with κ offsetsθmax = 27.4°, θmin = 2.9°
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
h = 1010
Tmin = 0.297, Tmax = 0.700k = 1010
4596 measured reflectionsl = 1010
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)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115H-atom parameters constrained
S = 1.17 w = 1/[σ2(Fo2) + (0.0584P)2 + 0.3136P]
where P = (Fo2 + 2Fc2)/3
1850 reflections(Δ/σ)max < 0.001
110 parametersΔρmax = 1.35 e Å3
0 restraintsΔρmin = 1.57 e Å3
Crystal data top
C6H3I2NO3γ = 67.3547 (15)°
Mr = 390.89V = 432.59 (3) Å3
Triclinic, P1Z = 2
a = 7.9749 (2) ÅMo Kα radiation
b = 8.0952 (3) ŵ = 7.24 mm1
c = 8.1395 (3) ÅT = 120 K
α = 69.3082 (18)°0.15 × 0.10 × 0.05 mm
β = 66.657 (2)°
Data collection top
Nonius KappaCCD
diffractometer
1850 independent reflections
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
1735 reflections with I > 2σ(I)
Tmin = 0.297, Tmax = 0.700Rint = 0.091
4596 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0320 restraints
wR(F2) = 0.115H-atom parameters constrained
S = 1.17Δρmax = 1.35 e Å3
1850 reflectionsΔρmin = 1.57 e Å3
110 parameters
Special details top

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G. C. & Holmes, K. C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High-redundancy data were used in the scaling program, hence the `multi-scan' code word was used.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.4568 (7)0.2563 (7)0.5717 (7)0.0151 (10)
O10.5878 (5)0.1050 (5)0.6302 (5)0.0168 (7)
C20.4701 (7)0.3379 (6)0.3843 (7)0.0165 (9)
I20.69997 (5)0.21823 (4)0.18496 (5)0.01781 (17)
C30.3342 (7)0.5005 (6)0.3318 (7)0.0153 (9)
C40.1880 (7)0.5757 (7)0.4659 (7)0.0161 (10)
N40.0478 (6)0.7482 (6)0.4127 (6)0.0188 (9)
O410.0820 (6)0.8178 (5)0.5346 (6)0.0265 (9)
O420.0673 (6)0.8160 (5)0.2483 (6)0.0263 (9)
C50.1632 (7)0.4974 (6)0.6545 (7)0.0166 (9)
C60.3004 (8)0.3383 (7)0.7039 (7)0.0170 (10)
I60.27464 (5)0.22289 (4)0.98238 (5)0.01917 (17)
H10.66260.05720.54140.025*
H30.34420.55670.20540.018*
H50.05640.55160.74490.020*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.012 (2)0.015 (2)0.018 (3)0.0026 (17)0.005 (2)0.0044 (19)
O10.0129 (16)0.0158 (16)0.0146 (18)0.0056 (13)0.0064 (15)0.0039 (14)
C20.019 (2)0.014 (2)0.014 (2)0.002 (2)0.004 (2)0.0050 (19)
I20.0144 (3)0.0183 (2)0.0159 (3)0.00020 (18)0.00123 (19)0.00785 (17)
C30.011 (2)0.014 (2)0.017 (2)0.0001 (17)0.006 (2)0.0018 (18)
C40.014 (2)0.015 (2)0.019 (3)0.0001 (18)0.009 (2)0.003 (2)
N40.0121 (18)0.0175 (18)0.023 (3)0.0005 (16)0.0037 (18)0.0076 (18)
O410.023 (2)0.0244 (19)0.017 (2)0.0041 (16)0.0031 (17)0.0101 (17)
O420.024 (2)0.0229 (19)0.020 (2)0.0076 (16)0.0129 (18)0.0002 (17)
C50.0074 (19)0.022 (2)0.019 (2)0.0034 (17)0.004 (2)0.0134 (19)
C60.018 (2)0.017 (2)0.015 (2)0.008 (2)0.002 (2)0.0073 (19)
I60.0178 (3)0.0189 (2)0.0137 (3)0.00060 (17)0.00289 (19)0.00438 (17)
Geometric parameters (Å, º) top
C1—O11.347 (6)C4—C51.402 (7)
C1—C61.399 (7)C4—N41.463 (6)
C1—C21.410 (7)N4—O421.224 (6)
O1—H10.8400N4—O411.227 (5)
C2—C31.400 (7)C5—C61.384 (7)
C2—I22.078 (5)C5—H50.9500
C3—C41.355 (7)C6—I62.082 (5)
C3—H30.9500
O1—C1—C6118.3 (5)C3—C4—N4118.7 (5)
O1—C1—C2123.5 (5)C5—C4—N4117.7 (4)
C6—C1—C2118.2 (5)O42—N4—O41123.4 (5)
C1—O1—H1109.5O42—N4—C4118.0 (4)
C3—C2—C1120.9 (5)O41—N4—C4118.5 (4)
C3—C2—I2120.1 (4)C6—C5—C4117.4 (5)
C1—C2—I2119.1 (4)C6—C5—H5121.3
C4—C3—C2118.2 (5)C4—C5—H5121.3
C4—C3—H3120.9C5—C6—C1121.7 (5)
C2—C3—H3120.9C5—C6—I6118.7 (4)
C3—C4—C5123.6 (4)C1—C6—I6119.6 (4)
C3—C4—N4—O41178.5 (6)C5—C4—N4—O411.4 (8)
C3—C4—N4—O421.1 (8)C5—C4—N4—O42179.1 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···I20.842.673.239 (4)126
O1—H1···O41i0.842.202.808 (6)129
Symmetry code: (i) x+1, y1, z.
(II) 2,6-Diiodo-4-nitrophenyl acetate top
Crystal data top
C8H5I2NO4F(000) = 792
Mr = 432.93Dx = 2.453 Mg m3
Orthorhombic, PnmaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2nCell parameters from 2206 reflections
a = 8.0608 (9) Åθ = 2.4–32.6°
b = 12.4501 (14) ŵ = 5.36 mm1
c = 11.6790 (13) ÅT = 292 K
V = 1172.1 (2) Å3Block, colourless
Z = 40.50 × 0.23 × 0.12 mm
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
2206 independent reflections
Radiation source: fine-focus sealed X-ray tube1555 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
ϕ and ω scansθmax = 32.6°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 1999)
h = 1212
Tmin = 0.258, Tmax = 0.528k = 1718
11456 measured reflectionsl = 1715
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.112 w = 1/[σ2(Fo2) + (0.0513P)2 + 0.8851P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
2206 reflectionsΔρmax = 1.20 e Å3
81 parametersΔρmin = 0.41 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0321 (13)
Crystal data top
C8H5I2NO4V = 1172.1 (2) Å3
Mr = 432.93Z = 4
Orthorhombic, PnmaMo Kα radiation
a = 8.0608 (9) ŵ = 5.36 mm1
b = 12.4501 (14) ÅT = 292 K
c = 11.6790 (13) Å0.50 × 0.23 × 0.12 mm
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
2206 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1999)
1555 reflections with I > 2σ(I)
Tmin = 0.258, Tmax = 0.528Rint = 0.044
11456 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.112H-atom parameters constrained
S = 1.04Δρmax = 1.20 e Å3
2206 reflectionsΔρmin = 0.41 e Å3
81 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.1503 (5)0.25000.1689 (3)0.0376 (7)
O10.1962 (3)0.25000.0539 (2)0.0406 (6)
C110.0705 (6)0.25000.0268 (3)0.0447 (9)
O120.0711 (5)0.25000.0010 (3)0.0801 (14)
C120.1402 (6)0.25000.1442 (3)0.0548 (12)
C20.1341 (3)0.3471 (2)0.2269 (2)0.0407 (6)
I20.16877 (4)0.49229 (2)0.14194 (2)0.06767 (17)
C30.1006 (4)0.3473 (3)0.3440 (2)0.0444 (6)
C40.0833 (5)0.25000.3985 (3)0.0436 (9)
N40.0485 (5)0.25000.5223 (3)0.0540 (10)
O40.0328 (4)0.3362 (3)0.5705 (2)0.0765 (9)
H12A0.06050.22020.19630.082*0.50
H12B0.23950.20750.14570.082*0.50
H12C0.16570.32230.16660.082*0.50
H30.09030.41140.38420.053*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0379 (18)0.048 (2)0.0274 (15)0.0000.0006 (13)0.000
O10.0390 (14)0.0558 (17)0.0270 (12)0.0000.0029 (10)0.000
C110.052 (2)0.051 (2)0.0312 (17)0.0000.0005 (16)0.000
O120.0437 (18)0.150 (5)0.0464 (19)0.0000.0016 (15)0.000
C120.064 (3)0.072 (3)0.0288 (18)0.0000.0013 (17)0.000
C20.0430 (14)0.0448 (14)0.0344 (12)0.0022 (11)0.0010 (10)0.0007 (10)
I20.1028 (3)0.04586 (18)0.0543 (2)0.00141 (11)0.00652 (12)0.00583 (9)
C30.0461 (14)0.0547 (17)0.0323 (12)0.0030 (13)0.0015 (11)0.0046 (11)
C40.0371 (19)0.068 (3)0.0255 (15)0.0000.0045 (14)0.000
N40.0471 (19)0.089 (3)0.0262 (15)0.0000.0035 (13)0.000
O40.088 (2)0.103 (2)0.0381 (12)0.0214 (16)0.0074 (12)0.0237 (14)
Geometric parameters (Å, º) top
C1—C2i1.392 (3)C2—C31.394 (4)
C1—C21.392 (3)C2—I22.080 (3)
C1—O11.393 (4)C3—C41.375 (4)
O1—C111.385 (5)C3—H30.9300
C11—O121.186 (6)C4—C3i1.375 (4)
C11—C121.481 (6)C4—N41.474 (5)
C12—H12A0.9600N4—O41.218 (3)
C12—H12B0.9600N4—O4i1.218 (3)
C12—H12C0.9600
C2i—C1—C2120.6 (3)C1—C2—C3119.7 (3)
C2i—C1—O1119.58 (17)C1—C2—I2120.7 (2)
C2—C1—O1119.58 (17)C3—C2—I2119.5 (2)
C11—O1—C1117.5 (3)C4—C3—C2118.2 (3)
O12—C11—O1121.2 (4)C4—C3—H3120.9
O12—C11—C12128.2 (4)C2—C3—H3120.9
O1—C11—C12110.6 (4)C3i—C4—C3123.4 (4)
C11—C12—H12A109.5C3i—C4—N4118.27 (18)
C11—C12—H12B109.5C3—C4—N4118.27 (18)
H12A—C12—H12B109.5O4—N4—O4i123.5 (4)
C11—C12—H12C109.5O4—N4—C4118.2 (2)
H12A—C12—H12C109.5O4i—N4—C4118.2 (2)
H12B—C12—H12C109.5
C2i—C1—O1—C1192.6 (3)I2—C2—C3—C4178.0 (3)
C1—O1—C11—O120.0C2—C3—C4—C3i1.4 (6)
C1—O1—C11—C12180.0C2—C3—C4—N4179.8 (3)
C2i—C1—C2—C30.3 (5)C3i—C4—N4—O4179.9 (4)
O1—C1—C2—C3175.1 (3)C3—C4—N4—O41.6 (6)
C2i—C1—C2—I2177.22 (18)C3i—C4—N4—O4i1.6 (6)
O1—C1—C2—I22.4 (4)C3—C4—N4—O4i179.9 (4)
C1—C2—C3—C40.5 (5)C2—C1—O1—C1192.6 (3)
Symmetry code: (i) x, y+1/2, z.
(III) 2,6-Diiodo-4-nitroanisole top
Crystal data top
C7H5I2NO3F(000) = 1472
Mr = 404.92Dx = 2.640 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2312 reflections
a = 15.2372 (3) Åθ = 2.9–27.5°
b = 16.2672 (4) ŵ = 6.15 mm1
c = 8.3262 (2) ÅT = 120 K
β = 99.2039 (15)°Block, yellow
V = 2037.22 (8) Å30.10 × 0.05 × 0.03 mm
Z = 8
Data collection top
Nonius KappaCCD
diffractometer
2312 independent reflections
Radiation source: fine-focus sealed X-ray tube2068 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.056
ϕ scans, and ω scans with κ offsetsθmax = 27.5°, θmin = 2.9°
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
h = 1919
Tmin = 0.530, Tmax = 0.829k = 2118
7397 measured reflectionsl = 1010
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)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0371P)2]
where P = (Fo2 + 2Fc2)/3
2312 reflections(Δ/σ)max < 0.001
119 parametersΔρmax = 1.42 e Å3
0 restraintsΔρmin = 1.65 e Å3
Crystal data top
C7H5I2NO3V = 2037.22 (8) Å3
Mr = 404.92Z = 8
Monoclinic, C2/cMo Kα radiation
a = 15.2372 (3) ŵ = 6.15 mm1
b = 16.2672 (4) ÅT = 120 K
c = 8.3262 (2) Å0.10 × 0.05 × 0.03 mm
β = 99.2039 (15)°
Data collection top
Nonius KappaCCD
diffractometer
2312 independent reflections
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
2068 reflections with I > 2σ(I)
Tmin = 0.530, Tmax = 0.829Rint = 0.056
7397 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0330 restraints
wR(F2) = 0.077H-atom parameters constrained
S = 1.07Δρmax = 1.42 e Å3
2312 reflectionsΔρmin = 1.65 e Å3
119 parameters
Special details top

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G. C. & Holmes, K. C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High-redundancy data were used in the scaling program, hence the `multi-scan' code word was used.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.2503 (3)0.0792 (3)0.2707 (5)0.0190 (8)
O10.30537 (18)0.02160 (17)0.2193 (3)0.0222 (6)
C110.3802 (3)0.0013 (3)0.3404 (6)0.0297 (10)
C20.2648 (3)0.1619 (3)0.2520 (5)0.0198 (8)
I20.371418 (17)0.199410 (16)0.13802 (3)0.02086 (11)
C30.2082 (3)0.2206 (3)0.2988 (4)0.0193 (8)
C40.1356 (3)0.1926 (3)0.3624 (5)0.0209 (10)
N40.0728 (2)0.2537 (2)0.4084 (4)0.0238 (8)
O410.0919 (2)0.32653 (19)0.4042 (4)0.0314 (7)
O420.0042 (2)0.2282 (2)0.4497 (4)0.0314 (7)
C50.1168 (3)0.1110 (3)0.3794 (4)0.0211 (9)
C60.1750 (3)0.0535 (3)0.3330 (5)0.0204 (8)
I60.146602 (18)0.071663 (18)0.34506 (3)0.02502 (12)
H11A0.41980.04610.36470.045*
H11B0.41270.04650.29870.045*
H11C0.35880.01900.43980.045*
H30.21900.27760.28760.023*
H50.06530.09430.42180.025*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.017 (2)0.025 (2)0.0138 (18)0.0011 (15)0.0008 (16)0.0007 (15)
O10.0237 (15)0.0216 (15)0.0219 (14)0.0020 (12)0.0054 (12)0.0007 (11)
C110.026 (2)0.031 (2)0.032 (2)0.0080 (18)0.0048 (18)0.0054 (18)
C20.0177 (19)0.026 (2)0.0160 (18)0.0006 (16)0.0027 (16)0.0007 (16)
I20.01738 (17)0.02245 (18)0.02354 (18)0.00091 (10)0.00564 (12)0.00054 (9)
C30.020 (2)0.023 (2)0.0139 (18)0.0010 (17)0.0014 (16)0.0000 (16)
C40.017 (2)0.029 (3)0.017 (2)0.0062 (16)0.0027 (18)0.0036 (15)
N40.0214 (19)0.030 (2)0.0198 (18)0.0017 (15)0.0018 (15)0.0036 (15)
O410.0319 (18)0.0261 (18)0.0371 (19)0.0035 (14)0.0080 (15)0.0030 (14)
O420.0215 (16)0.042 (2)0.0325 (17)0.0003 (14)0.0092 (14)0.0066 (15)
C50.016 (2)0.033 (2)0.0149 (18)0.0009 (17)0.0029 (16)0.0002 (16)
C60.020 (2)0.024 (2)0.0161 (19)0.0026 (17)0.0008 (16)0.0010 (15)
I60.02599 (19)0.0248 (2)0.02382 (18)0.00485 (11)0.00265 (13)0.00228 (10)
Geometric parameters (Å, º) top
C1—O11.372 (5)C3—C41.378 (6)
C1—C21.376 (6)C3—H30.9500
C1—C61.396 (6)C4—C51.371 (6)
O1—C111.444 (5)C4—N41.472 (5)
C11—H11A0.9800N4—O411.222 (5)
C11—H11B0.9800N4—O421.223 (5)
C11—H11C0.9800C5—C61.385 (6)
C2—C31.384 (6)C5—H50.9500
C2—I22.099 (4)C6—I62.087 (4)
O1—C1—C2120.9 (4)C4—C3—H3121.4
O1—C1—C6119.4 (4)C2—C3—H3121.4
C2—C1—C6119.5 (4)C5—C4—C3123.6 (4)
C1—O1—C11114.4 (3)C5—C4—N4118.1 (4)
O1—C11—H11A109.5C3—C4—N4118.2 (4)
O1—C11—H11B109.5O41—N4—O42123.7 (4)
H11A—C11—H11B109.5O41—N4—C4118.6 (3)
O1—C11—H11C109.5O42—N4—C4117.7 (4)
H11A—C11—H11C109.5C4—C5—C6118.1 (4)
H11B—C11—H11C109.5C4—C5—H5120.9
C1—C2—C3121.5 (4)C6—C5—H5120.9
C1—C2—I2119.1 (3)C5—C6—C1120.1 (4)
C3—C2—I2119.3 (3)C5—C6—I6119.9 (3)
C4—C3—C2117.1 (4)C1—C6—I6119.9 (3)
C3—C4—N4—O417.4 (5)C5—C4—N4—O424.5 (5)
C3—C4—N4—O42173.0 (4)C2—C1—O1—C1189.7 (5)
C5—C4—N4—O41175.1 (4)C6—C1—O1—C1194.7 (5)

Experimental details

(I)(II)(III)
Crystal data
Chemical formulaC6H3I2NO3C8H5I2NO4C7H5I2NO3
Mr390.89432.93404.92
Crystal system, space groupTriclinic, P1Orthorhombic, PnmaMonoclinic, C2/c
Temperature (K)120292120
a, b, c (Å)7.9749 (2), 8.0952 (3), 8.1395 (3)8.0608 (9), 12.4501 (14), 11.6790 (13)15.2372 (3), 16.2672 (4), 8.3262 (2)
α, β, γ (°)69.3082 (18), 66.657 (2), 67.3547 (15)90, 90, 9090, 99.2039 (15), 90
V3)432.59 (3)1172.1 (2)2037.22 (8)
Z248
Radiation typeMo KαMo KαMo Kα
µ (mm1)7.245.366.15
Crystal size (mm)0.15 × 0.10 × 0.050.50 × 0.23 × 0.120.10 × 0.05 × 0.03
Data collection
DiffractometerNonius KappaCCD
diffractometer
Bruker SMART 1000 CCD area-detector
diffractometer
Nonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
Multi-scan
(SADABS; Bruker, 1999)
Multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
Tmin, Tmax0.297, 0.7000.258, 0.5280.530, 0.829
No. of measured, independent and
observed [I > 2σ(I)] reflections
4596, 1850, 1735 11456, 2206, 1555 7397, 2312, 2068
Rint0.0910.0440.056
(sin θ/λ)max1)0.6480.7580.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.115, 1.17 0.041, 0.112, 1.04 0.033, 0.077, 1.07
No. of reflections185022062312
No. of parameters11081119
H-atom treatmentH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.35, 1.571.20, 0.411.42, 1.65

Computer programs: KappaCCD Server Software (Nonius, 1997), SMART (Bruker, 1999), DENZO-SMN (Otwinowski & Minor, 1997), SAINT (Bruker, 1999), DENZO-SMN, SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2002), SHELXL97 and PRPKAPPA (Ferguson, 1999).

Selected torsion angles (º) for (I) top
C3—C4—N4—O41178.5 (6)C3—C4—N4—O421.1 (8)
Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O41i0.842.202.808 (6)129
Symmetry code: (i) x+1, y1, z.
Selected torsion angles (º) for (II) top
C3—C4—N4—O41.6 (6)C2—C1—O1—C1192.6 (3)
C3—C4—N4—O4i179.9 (4)
Symmetry code: (i) x, y+1/2, z.
Selected torsion angles (º) for (III) top
C3—C4—N4—O417.4 (5)C2—C1—O1—C1189.7 (5)
C3—C4—N4—O42173.0 (4)C6—C1—O1—C1194.7 (5)
 

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