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In 2-hydroxy-3-iodo-5-nitro­benz­aldehyde, C7H4INO4, the mol­ecules are linked into sheets by a combination of C—H...O hydrogen bonds and two-centre iodo–nitro interactions, and these sheets are linked by aromatic π–π stacking interactions. Molecules of 2,4-di­iodo-6-nitro­anisole, C7H5I2NO3, are disordered, with the nitro group and one of the I substituents each occupying common sets of sites with 0.5 occupancy. The mol­ecules are linked into isolated centrosymmetric dimeric units by a single iodo–nitro interaction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270103025654/gg1198sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270103025654/gg1198Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270103025654/gg1198IIsup3.hkl
Contains datablock II

CCDC references: 231051; 231052

Comment top

We have recently reported the supramolecular aggregation of a wide range of different types of iodo-nitro aromatic compounds (McWilliam et al., 2001; Garden, da Cunha et al., 2002; Garden, Fontes et al., 2002; Kelly et al., 2002; Glidewell, Howie et al., 2002; Glidewell, Low et al., 2002; Glidewell et al., 2003), in which the patterns of supramolecular aggregation depend on the interplay of a wide range of weak intermolecular forces, including hard and soft (Desiraju & Steiner, 1999) hydrogen bonds of various types, iodo···nitro interactions and aromatic ππ stacking interactions. Here, we report the molecular and supramolecular structures of two further examples of such compounds, 2-hydroxy-3-iodo-5-nitrobenzaldehyde, (I), and 2,4-diiodo-6-nitroanisole, (II), the latter being isomeric with 2,6-diiodo-4-nitroanisole, (III) (Garden, da Cunha et al., 2002). \sch

In compound (I) [Fig. 1, where the crystallographic atom-numbering scheme differs from the conventional chemical numbering scheme, in order that both (I) and (II) have a nitro group at position 1 and an iodo substituent at position 5], there is an intramolecular O—H···O hydrogen bond, forming an S(6) motif (Bernstein et al., 1995). There are three distinct types of intermolecular interactions linking the molecules of (I). A soft hydrogen bond and an iodo···nitro interaction each form a chain motif. Thus, aromatic atom C6 in the molecule at (x, y, z) acts as hydrogen-bond donor to the aldehydic atom O31 in the molecule at (1 + x, y, z), so generating by translation a C(7) chain running parallel to the [100] direction (Fig. 2). At the same time, atom I5 in the molecule at (x, y, z) forms a short two-centre iodo···nitro interaction with nitro atom O11 in the molecule at (1 − x, 1/2 + y, 1/2 − z), with I···O 3.054 (3) Å, C—I···O 167.8 (2)° and I···O—N 116.0 (2)°, so producing a C(6) chain (Starbuck et al., 1999) running parallel to the [010] direction and generated by the 21 screw axis along (1/2, y, 1/4). The combination of the [100] and [010] chains generates an elegant sheet parallel to (001), in the form of a (4,4) net (Batten & Robson, 1998) containing equal numbers of S(6) and R54(22) rings (Fig. 2).

Two sheets of this type pass through each unit cell of (I), lying in the domains 0.09 < z < 0.41 and 0.59 < z < 0.91, and adjacent sheets are weakly linked by the third type of intermolecular interaction, an aromatic ππ stacking interaction. The aryl ring in the molecule at (x, y, z), which lies in the 0.09 < z < 0.41 sheet, and those in the molecules at (x, 1/2 − y, 1/2 + z) and (x, 1/2 − y, z − 1/2), which lie in the domains 0.59 < z < 0.91 and −0.41 < z < −0.09, respectively, are nearly parallel, with an interplanar angle between rings in adjacent sheets of only ca 1.3°. The centroid separations are both 3.767 (3) Å and the interplanar separations are ca 3.46 Å, corresponding to centroid offsets of ca 1.49 Å (Fig. 3).

In the disordered structure of (II) (Fig. 4, where again the crystallographic atom-numbering scheme differs from the conventional chemical numbering scheme, see above), in contrast with (I), there are neither C—H···O hydrogen bonds nor aromatic ππ stacking interactions. The only direction-specific intermolecular interaction is a two-centre iodo···nitro interaction involving the fully occupied I5 site and the half-occupied O1 site in the molecules at (x, y, z) and (1/2 − x, 1/2 − y, 1 − z), with I···O 3.339 (13) Å, C—I···O 148.5 (2)° and I···O—N 135.3 (13)°. If the O11 sites in both of these molecules were fully occupied, the resulting dimer would contain an R22(14) motif (Fig. 5). However, each such pair of molecules may, in fact, contain two, one or zero I···O interactions, depending upon the local occupancy of the O11 sites, with an average value of one. There are four of these dimeric aggregates in each unit cell of (II), but there are no direction-specific interactions between them. In the isomeric compound, (III), the fully ordered molecules are linked into isolated chains by a single two-centre iodo···nitro interaction (Garden, da Cunha et al., 2002). The intramolecular distances and angles in (I) and (II) present no unusual features.

Experimental top

To prepare compound (I), 5-nitrosalicaldehyde (10 mmol) was dissolved in warm methanol (30 ml) and a solution of K[ICl2] in methanol (2 M, 10 ml) was added with stirring. After a few hours, the reaction mixture was diluted with water (100 ml) and compound (I) was collected by filtration, washed with water and crystallized from aqueous ethanol (yield 83%, m. p. 432–433 K). To prepare compound (II), a solution of K[ICl2] in methanol (2 M, 25 ml) was added to a methanolic solution (50 ml) of 2-nitrophenol (20 mmol) and the mixture was gently warmed. Water (100 ml) was added to the reaction mixture and 2,4-diiodo-6-nitrophenol was precipitated out, collected by filtration and washed with water. This material was dissolved in acetone (50 ml) and to this solution was added K2CO3 (30 mmol) followed by an excess of Me2SO4 (10 ml). The resulting mixture was stirred at room temperature for 3 d, after which time the reaction mixture was concentrated by evaporation of the volatiles. The addition of water (100 ml) precipitated compound (II), which was collected by filtration and crystallized from aqueous ethanol (yield 93%, m. p. 385–386 K).

Refinement top

Crystals of (I) and (II) are monoclinic. For (I), the space group P21/c was uniquely assigned from the systematic absences, while for (II), the systematic absences permitted Cc and C2/c as possible space groups; C2/c was selected, and confirmed by the subsequent structure analysis. It was apparent at an early stage that the molecules of (II) were disordered over two sets of sites such that all atoms, except one nitro group and one I atom, were common to both orientations. When the site-occupancy factors for these disordered substituents were refined they gave values of 0.48 (3) and 0.52 (3), and hence they were both thereafter fixed at 0.50. When full anisotropic refinement was attempted for (II), the behaviour of the disordered nitro groups was erratic and not satisfactory. Accordingly, the atoms in these substituents were constrained to have the same anisotropic displacement parameters and the refinement then behaved satisfactorily. All H atoms were located from difference maps and then treated as riding atoms, with C—H distances of 0.93 (aromatic and CHO) and 0.96 Å (methyl), and O—H distances of 0.82 Å.

Computing details top

For both compounds, data collection: KappaCCD Server Software (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 and H atoms are shown as small spheres of arbitrary radii.
[Figure 2] Fig. 2. Part of the crystal structure of (I), showing the formation of an (001) sheet built from C—H···O hydrogen bonds and iodo···nitro interactions. The atoms marked with an asterisk (*), hash (#) or dollar sign ($) are at the symmetry positions (1 + x, y, z), (1 − x, 1/2 + y, 1/2 − z) and (x, 1 + y, z), respectively.
[Figure 3] Fig. 3. A stereoview of part of the crystal structure of (I), showing the ππ stacking interaction which links adjacent (001) sheets. For the sake of clarity, H atoms have been omitted.
[Figure 4] Fig. 4. A view of the molecule of (II), showing the atom-labelling scheme and the disorder (see text). Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
[Figure 5] Fig. 5. Part of the crystal structure of (II), showing the formation of an R22(14) dimer. For the sake of clarity, only one orientation of the disordered components is shown, and the H atoms and the unit-cell box have been omitted. The atoms marked with an asterisk (*) are at the symmetry position (1/2 − x, 1/2 − y, 1 − z).
(I) 2-Hydroxy-3-iodo-5-nitrobenzaldehyde top
Crystal data top
C7H4INO4F(000) = 552
Mr = 293.01Dx = 2.348 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1901 reflections
a = 8.2556 (3) Åθ = 3.0–27.5°
b = 15.3414 (8) ŵ = 3.84 mm1
c = 7.2521 (4) ÅT = 120 K
β = 115.496 (3)°Lath, colourless
V = 829.05 (7) Å30.36 × 0.05 × 0.02 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer
1901 independent reflections
Radiation source: rotating anode1482 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.065
ϕ scans, and ω scans with κ offsetsθmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
h = 1010
Tmin = 0.339, Tmax = 0.927k = 1919
8251 measured reflectionsl = 99
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) = 0.074H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0348P)2]
where P = (Fo2 + 2Fc2)/3
1901 reflections(Δ/σ)max = 0.001
119 parametersΔρmax = 1.13 e Å3
0 restraintsΔρmin = 1.08 e Å3
Crystal data top
C7H4INO4V = 829.05 (7) Å3
Mr = 293.01Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.2556 (3) ŵ = 3.84 mm1
b = 15.3414 (8) ÅT = 120 K
c = 7.2521 (4) Å0.36 × 0.05 × 0.02 mm
β = 115.496 (3)°
Data collection top
Nonius KappaCCD
diffractometer
1901 independent reflections
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
1482 reflections with I > 2σ(I)
Tmin = 0.339, Tmax = 0.927Rint = 0.065
8251 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0330 restraints
wR(F2) = 0.074H-atom parameters constrained
S = 1.03Δρmax = 1.13 e Å3
1901 reflectionsΔρmin = 1.08 e Å3
119 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.2059 (6)0.1453 (2)0.1802 (6)0.0135 (8)
N10.3257 (5)0.0711 (2)0.2125 (5)0.0170 (8)
O110.4865 (4)0.08468 (18)0.2696 (5)0.0236 (7)
O120.2593 (4)0.00229 (19)0.1838 (5)0.0252 (8)
C20.0318 (6)0.1324 (3)0.1491 (6)0.0174 (9)
C30.0769 (6)0.2043 (3)0.1281 (6)0.0160 (9)
C40.0087 (6)0.2900 (3)0.1386 (6)0.0159 (9)
C50.1703 (6)0.3002 (2)0.1698 (6)0.0157 (9)
I50.28173 (4)0.424544 (16)0.19310 (4)0.02033 (12)
C60.2773 (6)0.2286 (3)0.1902 (5)0.0153 (8)
C310.2675 (6)0.1906 (3)0.1045 (6)0.0168 (9)
O310.3591 (4)0.2513 (2)0.1010 (5)0.0277 (7)
O410.1079 (4)0.36054 (18)0.1176 (5)0.0231 (7)
H20.01290.07620.14210.021*
H310.31300.13440.09270.020*
H410.20280.34660.12020.035*
H60.39570.23570.21060.018*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.017 (2)0.0113 (19)0.0123 (19)0.0047 (17)0.0061 (17)0.0005 (15)
N10.023 (2)0.0131 (19)0.0169 (17)0.0002 (16)0.0102 (16)0.0027 (14)
O110.0198 (19)0.0181 (17)0.0352 (18)0.0013 (13)0.0140 (15)0.0013 (13)
O120.031 (2)0.0124 (16)0.0347 (19)0.0029 (13)0.0168 (17)0.0038 (13)
C20.021 (3)0.015 (2)0.016 (2)0.0040 (18)0.0067 (18)0.0019 (16)
C30.017 (2)0.016 (2)0.0151 (19)0.0010 (17)0.0073 (18)0.0005 (16)
C40.022 (2)0.016 (2)0.0116 (18)0.0022 (18)0.0093 (17)0.0009 (16)
C50.022 (3)0.013 (2)0.0143 (19)0.0019 (17)0.0095 (18)0.0016 (15)
I50.0290 (2)0.01252 (17)0.02228 (17)0.00365 (12)0.01369 (13)0.00179 (12)
C60.021 (2)0.015 (2)0.0128 (18)0.0016 (18)0.0094 (17)0.0011 (16)
C310.030 (3)0.008 (2)0.0111 (19)0.0020 (19)0.0073 (18)0.0020 (16)
O310.0204 (18)0.0314 (19)0.0332 (18)0.0028 (15)0.0133 (15)0.0099 (14)
O410.0223 (19)0.0158 (15)0.0377 (18)0.0059 (13)0.0189 (16)0.0042 (13)
Geometric parameters (Å, º) top
C1—C21.370 (6)C2—H20.93
C2—C31.389 (6)C3—C311.522 (6)
C3—C41.419 (5)C31—O311.193 (5)
C4—C51.404 (6)C31—H310.93
C5—C61.376 (6)C4—O411.327 (5)
C6—C11.396 (6)O41—H410.82
C1—N11.459 (5)C5—I52.093 (4)
N1—O111.226 (5)C6—H60.93
N1—O121.231 (4)
C2—C1—C6122.0 (4)O31—C31—H31119.7
C2—C1—N1120.3 (4)C3—C31—H31119.7
C6—C1—N1117.6 (4)O41—C4—C5118.9 (4)
O11—N1—O12123.4 (4)O41—C4—C3122.6 (4)
O11—N1—C1118.9 (3)C5—C4—C3118.6 (4)
O12—N1—C1117.7 (4)C4—O41—H41109.5
C1—C2—C3119.1 (4)C6—C5—C4120.7 (4)
C1—C2—H2120.4C6—C5—I5118.6 (3)
C3—C2—H2120.4C4—C5—I5120.7 (3)
C2—C3—C4120.4 (4)C5—C6—C1119.2 (4)
C2—C3—C31119.4 (4)C5—C6—H6120.4
C4—C3—C31120.1 (4)C1—C6—H6120.4
O31—C31—C3120.7 (4)
C2—C1—N1—O11169.4 (4)C31—C3—C4—O413.7 (6)
C6—C1—N1—O118.2 (5)C2—C3—C4—C50.2 (6)
C2—C1—N1—O129.5 (5)C31—C3—C4—C5177.1 (3)
C6—C1—N1—O12173.0 (3)O41—C4—C5—C6179.4 (3)
C6—C1—C2—C30.4 (6)C3—C4—C5—C60.1 (6)
N1—C1—C2—C3177.0 (3)O41—C4—C5—I52.1 (5)
C1—C2—C3—C40.1 (6)C3—C4—C5—I5178.7 (3)
C1—C2—C3—C31176.9 (4)C4—C5—C6—C10.2 (6)
C2—C3—C31—O31174.6 (4)I5—C5—C6—C1178.4 (3)
C4—C3—C31—O312.4 (6)C2—C1—C6—C50.4 (6)
C2—C3—C4—O41179.4 (4)N1—C1—C6—C5177.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O41—H41···O310.821.922.629 (5)145
C6—H6···O31i0.932.483.351 (6)155
Symmetry code: (i) x+1, y, z.
(II) 2,4-Diiodo-6-nitroanisole top
Crystal data top
C7H5I2NO3F(000) = 1472
Mr = 404.92Dx = 2.609 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 3712 reflections
a = 32.999 (2) Åθ = 2.5–32.6°
b = 4.2305 (3) ŵ = 6.08 mm1
c = 14.8328 (11) ÅT = 120 K
β = 95.225 (2)°Needle, colourless
V = 2062.1 (2) Å30.34 × 0.04 × 0.04 mm
Z = 8
Data collection top
Nonius KappaCCD
diffractometer
3712 independent reflections
Radiation source: rotating anode1520 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
ϕ scans, and ω scans with κ offsetsθmax = 32.6°, θmin = 2.5°
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
h = 4933
Tmin = 0.232, Tmax = 0.793k = 66
10606 measured reflectionsl = 2222
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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154H-atom parameters constrained
S = 0.89 w = 1/[σ2(Fo2) + (0.0721P)2]
where P = (Fo2 + 2Fc2)/3
3712 reflections(Δ/σ)max < 0.001
126 parametersΔρmax = 1.07 e Å3
10 restraintsΔρmin = 1.29 e Å3
Crystal data top
C7H5I2NO3V = 2062.1 (2) Å3
Mr = 404.92Z = 8
Monoclinic, C2/cMo Kα radiation
a = 32.999 (2) ŵ = 6.08 mm1
b = 4.2305 (3) ÅT = 120 K
c = 14.8328 (11) Å0.34 × 0.04 × 0.04 mm
β = 95.225 (2)°
Data collection top
Nonius KappaCCD
diffractometer
3712 independent reflections
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
1520 reflections with I > 2σ(I)
Tmin = 0.232, Tmax = 0.793Rint = 0.044
10606 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05310 restraints
wR(F2) = 0.154H-atom parameters constrained
S = 0.89Δρmax = 1.07 e Å3
3712 reflectionsΔρmin = 1.29 e Å3
126 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.1408 (2)0.3638 (13)0.5217 (3)0.0539 (15)
I10.14846 (4)0.5738 (3)0.64326 (6)0.0692 (3)0.50
N10.1473 (4)0.525 (4)0.6090 (6)0.113 (2)0.50
O110.1770 (3)0.691 (3)0.6295 (7)0.113 (2)0.50
O120.1220 (3)0.486 (4)0.6629 (8)0.113 (2)0.50
C20.10114 (19)0.3350 (13)0.4756 (4)0.0488 (14)
O210.06871 (13)0.4760 (11)0.5092 (3)0.0616 (12)
C210.0465 (2)0.2755 (19)0.5662 (5)0.077 (2)
C30.09815 (15)0.1894 (15)0.3909 (4)0.0518 (15)
N30.0590 (2)0.162 (4)0.3371 (6)0.113 (2)0.50
O310.0584 (3)0.149 (4)0.2548 (7)0.113 (2)0.50
O320.0272 (3)0.140 (4)0.3726 (7)0.113 (2)0.50
I30.04405 (3)0.1563 (3)0.31796 (6)0.0732 (3)0.50
C40.1321 (2)0.0604 (15)0.3566 (4)0.0590 (17)
C50.17055 (19)0.0899 (15)0.4032 (4)0.0540 (15)
I50.221995 (15)0.09284 (11)0.34922 (4)0.0749 (2)
C60.1749 (2)0.2420 (16)0.4848 (4)0.0574 (16)
H21A0.03160.11990.52960.115*
H21B0.02790.40160.59710.115*
H21C0.06530.17180.60980.115*
H40.12920.04740.30170.071*
H60.20060.26420.51570.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.070 (4)0.047 (4)0.045 (3)0.002 (3)0.007 (3)0.010 (3)
I10.0891 (7)0.0674 (6)0.0507 (5)0.0001 (6)0.0045 (5)0.0066 (4)
N10.085 (4)0.157 (6)0.095 (4)0.006 (4)0.000 (4)0.030 (4)
O110.085 (4)0.157 (6)0.095 (4)0.006 (4)0.000 (4)0.030 (4)
O120.085 (4)0.157 (6)0.095 (4)0.006 (4)0.000 (4)0.030 (4)
C20.056 (4)0.048 (3)0.044 (3)0.006 (3)0.015 (3)0.007 (3)
O210.060 (3)0.065 (3)0.063 (3)0.015 (2)0.021 (2)0.004 (2)
C210.067 (5)0.093 (5)0.074 (5)0.002 (4)0.033 (4)0.004 (4)
C30.048 (3)0.060 (4)0.048 (3)0.002 (3)0.007 (3)0.000 (3)
N30.085 (4)0.157 (6)0.095 (4)0.006 (4)0.000 (4)0.030 (4)
O310.085 (4)0.157 (6)0.095 (4)0.006 (4)0.000 (4)0.030 (4)
O320.085 (4)0.157 (6)0.095 (4)0.006 (4)0.000 (4)0.030 (4)
I30.0548 (6)0.1124 (9)0.0518 (5)0.0057 (6)0.0013 (4)0.0050 (5)
C40.070 (4)0.057 (4)0.053 (4)0.002 (3)0.025 (3)0.003 (3)
C50.053 (4)0.051 (4)0.062 (4)0.000 (3)0.027 (3)0.013 (3)
I50.0687 (3)0.0625 (3)0.0993 (4)0.0104 (2)0.0396 (3)0.0057 (3)
C60.054 (4)0.061 (4)0.059 (4)0.002 (3)0.013 (3)0.001 (3)
Geometric parameters (Å, º) top
C1—C61.394 (9)C21—H21C0.96
C1—C21.427 (9)C3—C41.383 (8)
C1—N11.4603 (10)C3—N31.4608 (10)
C1—I12.005 (5)C3—I32.007 (5)
N1—O121.2203 (10)N3—O311.2202 (10)
N1—O111.2205 (10)N3—O321.2204 (10)
C2—O211.359 (7)C4—C51.395 (10)
C2—C31.394 (8)C4—H40.93
O21—C211.443 (8)C5—C61.368 (9)
C21—H21A0.96C5—I52.090 (6)
C21—H21B0.96C6—H60.93
C6—C1—C2121.3 (5)C4—C3—C2120.8 (5)
C6—C1—N1117.5 (8)C4—C3—N3118.2 (7)
C2—C1—N1121.3 (7)C2—C3—N3120.9 (7)
C6—C1—I1118.5 (5)C4—C3—I3118.9 (4)
C2—C1—I1120.3 (4)C2—C3—I3120.2 (4)
O12—N1—O11119.61 (15)O31—N3—O32119.57 (15)
O12—N1—C1117.7 (9)O31—N3—C3118.8 (8)
O11—N1—C1122.7 (9)O32—N3—C3121.5 (8)
O21—C2—C3122.1 (5)C3—C4—C5120.9 (6)
O21—C2—C1120.4 (5)C3—C4—H4119.6
C3—C2—C1117.2 (5)C5—C4—H4119.6
C2—O21—C21114.5 (5)C6—C5—C4119.9 (6)
O21—C21—H21A109.5C6—C5—I5119.3 (5)
O21—C21—H21B109.5C4—C5—I5120.8 (5)
H21A—C21—H21B109.5C5—C6—C1119.8 (6)
O21—C21—H21C109.5C5—C6—H6120.1
H21A—C21—H21C109.5C1—C6—H6120.1
H21B—C21—H21C109.5
C6—C1—N1—O12142.1 (13)O21—C2—C3—I34.3 (8)
C2—C1—N1—O1238.5 (18)C1—C2—C3—I3177.0 (4)
I1—C1—N1—O1221 (19)C4—C3—N3—O3128.8 (19)
C6—C1—N1—O1137.2 (19)C2—C3—N3—O31152.6 (13)
C2—C1—N1—O11142.2 (14)I3—C3—N3—O31138 (54)
I1—C1—N1—O11158 (21)C4—C3—N3—O32148.1 (14)
C6—C1—C2—O21174.9 (5)C2—C3—N3—O3230 (2)
N1—C1—C2—O214.5 (11)I3—C3—N3—O3245 (52)
I1—C1—C2—O216.4 (7)C2—C3—C4—C54.0 (10)
C6—C1—C2—C32.1 (8)N3—C3—C4—C5177.4 (9)
N1—C1—C2—C3177.3 (9)I3—C3—C4—C5177.2 (5)
I1—C1—C2—C3179.3 (4)C3—C4—C5—C61.4 (9)
C3—C2—O21—C2193.7 (7)C3—C4—C5—I5178.1 (5)
C1—C2—O21—C2193.8 (7)C4—C5—C6—C10.8 (9)
O21—C2—C3—C4177.0 (6)I5—C5—C6—C1179.7 (4)
C1—C2—C3—C44.2 (9)C2—C1—C6—C50.4 (9)
O21—C2—C3—N34.5 (11)N1—C1—C6—C5179.8 (9)
C1—C2—C3—N3177.2 (9)I1—C1—C6—C5178.2 (5)

Experimental details

(I)(II)
Crystal data
Chemical formulaC7H4INO4C7H5I2NO3
Mr293.01404.92
Crystal system, space groupMonoclinic, P21/cMonoclinic, C2/c
Temperature (K)120120
a, b, c (Å)8.2556 (3), 15.3414 (8), 7.2521 (4)32.999 (2), 4.2305 (3), 14.8328 (11)
β (°) 115.496 (3) 95.225 (2)
V3)829.05 (7)2062.1 (2)
Z48
Radiation typeMo KαMo Kα
µ (mm1)3.846.08
Crystal size (mm)0.36 × 0.05 × 0.020.34 × 0.04 × 0.04
Data collection
DiffractometerNonius KappaCCD
diffractometer
Nonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
Multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
Tmin, Tmax0.339, 0.9270.232, 0.793
No. of measured, independent and
observed [I > 2σ(I)] reflections
8251, 1901, 1482 10606, 3712, 1520
Rint0.0650.044
(sin θ/λ)max1)0.6500.758
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.074, 1.03 0.053, 0.154, 0.89
No. of reflections19013712
No. of parameters119126
No. of restraints010
H-atom treatmentH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.13, 1.081.07, 1.29

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

Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
O41—H41···O310.821.922.629 (5)145
C6—H6···O31i0.932.483.351 (6)155
Symmetry code: (i) x+1, y, z.
 

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