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The crystal packing of 1-iodo-3-nitro­benzene, C6H4INO2, is formed by planar mol­ecules which are linked by I...I and NO2...NO2 interactions. In the case of 1-iodo-3,5-di­nitro­benzene, C6H3IN2O4, the NO2 groups are not exactly coplanar with the benzene ring and the mol­ecules form sheets linked by NO2...NO2 interactions. In contrast with 4-iodo­nitro­benzene, the crystal structures of both title compounds do not form highly symmetrical I...NO2 intermolecular interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270102023041/dn1017sup1.cif
Contains datablocks global, II, III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270102023041/dn1017IIsup2.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270102023041/dn1017IIIsup3.hkl
Contains datablock III

CCDC references: 195181; 195182

Comment top

In this communication, we report the crystal structures of two iodo-substituted nitrobenzenes. A comparison with related iodo-substituted nitrobenzenes shows that the different possibilities of I···NO2 interactions depend on the substitution pattern of the nitro and iodo groups on the benzene ring. Recently, Desiraju et al. (1993) observed that halogen atoms, presumably due to their polarizabilities, may form symmetrical (P) and unsymmetrical (Q, R) recognition motifs with nitro groups; Scheme 1 illustrates these types of iodo···nitro intermolecular interactions. Add Scheme 1 tag.

In the structures of 4-iodonitrobenzene, (I) (Thalladi et al., 1996), and the 1:1 complex of 1,4-dinitrobenzene and 1,4-diiodobenzene (Allen et al., 1994), there are linear ribbon patterns linked exclusively via symmetrical iodo···nitro motifs (P). These motifs are formed from two convergent polarization-induced I···O interactions. As part of a continuing study of intermolecular interactions in such compounds, we have investigated compounds containing 3-iodonitrobenzene substitution patterns and have determined the crystal structures of 3-iodo-1-nitrobenzene, (II), and 3-iodo-1,5-dinitro-benzene, (III). \sch

A search of the Spring 2002 release of the Cambridge Structural Database (CSD: Allen, 2002) for structures containing 3-iodonitrobenzene substitution patterns revealed only a few compounds containing additional groups on the aromatic system.

The molecular structure of (II) is shown in Fig. 1a, with the associated distances and angles of special interest given in Table 1. The C—I [2.095 (7) Å] and N—O [1.224 (8) and 1.242 (8) Å] distances are in good agreement with values reported for (I) [C—I 2.097 (5), and N—O 1.2242 (6) and 1.232 (6) Å; Thalladi et al., 1996]. The planar molecules are linked into zigzag chains by I···Ii interactions of 3.990 (7) Å [Fig. 1 b; symmetry code: (i) −x, 1/2 + y, −z]. A similar pattern of I···I zigzag chains has also been observed for 1,2-diiodo-4-nitro-5-(n-butylamino)benzene (Senskey et al., 1995). The overall network is formed using additional NO2···NO2 interactions, with O2N1···O2iiNO 2.928 (12) Å [symmetry code: (ii) 1 − x, 1/2 + y, 1 − z]. These distances are within the acceptable limits described in the literature for 1,2,4-trinitrobenzene (Laerdahl et al., 1998). In contrast with the crystal structures of (I) and related compounds, the lack of iodo···nitro interactions in (II) is surprising.

In an attempt to engineer a two-dimensional network with high symmetric P motifs, we looked to iodo-substituted nitrobenzene with additional nitro groups on the ring and determined the structure of 3-iodo-1,5-dinitrobenzene, (III). The molecular structure of (III) is shown in Fig. 2a, with the associated dimensions given in Table 2. The C—I and N—O distances are in good agreement with the determined structures of (I) and (II). Neither NO2 group is exactly coplanar with the benzene ring. The angles between the least-squares planes of the nitro groups and the benzene ring are 13 and 21°. The crystal packing of (II) can be described as a periodical arrangement of two nearly parallel sheets of molecules (Fig. 2 b), and two such sheets are linked by NO2···NO2 interactions, with N1iii···O1iv 2.944 (7) Å [symmetry codes: (iii) 1/2 + x, 1/2 − y, 1/2 + z; (iv) 1/2 − x, 1/2 − y, −z]. Each sheet forms I···NO2 interactions, with I1v···O2iii 3.206 (3) Å [symmetry code: (v) 1/2 + x, 1/2 + y, z], which conforms to the R type of motif, with only one of the two nitro O atoms in contact with an I atom. The presence of one iodo and two nitro groups is still not sufficient to engineer crystal packings containing symmetrical P motifs as building blocks.

In contrast, the higher-substituted compound 2-iodo-1,3,5-trinitrobenzene, (IV) (Weiss et al., 1999), forms planes using I···NO2 P motifs and these planes are linked by NO2···NO2 interactions. The P motifs are generated by the nitro and iodo groups arranged in the para position. A comparison of selected N—O–, N—C– and C—I bond lengths and angles of compounds (I)-(IV) shows no significant differences to explain the presence of different intermolecular interactions.

We have compared these structures with related iodo-substituted nitrobenzenes containing additional substituents, such as I (Garden et al., 2002), NH2 (McWilliams et al., 2001), NHR (Senskey et al., 1995) and OH (Garden et al., 2002). In these crystal packings, we only observed the I···NO2 interactions of the type P motif if the nitro and iodo groups were arranged in the para position. Fundamental organic chemistry suggests that there is a reactivity difference between meta- and para-substituted benzene rings. These differences are based on electronic arguments.

In this case, however, additional substitution in the ortho or meta position has no effect; it is only those complexes with I in the para position which display the P-type motif of crystal packing. Allen et al. (1997) combined a CSD search and an ab initio orbital study of the geometrical parameters of halogen···nitro supramolecular synthons. These indicated that halogen···nitro interactions increase in strength in the order Cl > Br > I, and that the frequency of formation of higher symmetrical motifs increases in the same order. To understand if there is a relationship between the role of substitution pattern on the benzene ring backbone and different types of intermolecular interactions, we will investigate other supramolecular synthons in the future.

Experimental top

Commercially available (Aldrich) 3-iodo-1-nitrobenzene, (II), and 3-iodo-1,5-dinitro-benzene, (III), were heated in acetone until most of the solid had dissolved. Crystals suitable for X-ray diffraction analysis were obtained by slow cooling of solutions in what? containing a few drops of heptane. Please give details of major solvent for crystallization.

Refinement top

For compound (II), the Friedel pairs were not merged, owing to the determination of the absolute structure by refining the Flack parameter (Flack, 1983). The number of Friedel pairs measured was 625. For both compounds, H atoms were treated as riding, with C—H distances of 0.94%A. Is this added text OK?

Computing details top

For both compounds, data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Siemens, 1996); program(s) used to refine structure: SHELXTL. Molecular graphics: SHELXTL for (II); SHELXTL and ORTEPIII (Farrugia, 1997) for (III). For both compounds, software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. (a) The molecular structure of (II) with ?? probability displacement ellipsoids. H atoms are shown as small spheres of arbitrary radii. (b) The crystal packing of (II). Please provide missing probability level.
[Figure 2] Fig. 2. (a) The molecular structure of (III) with ?? probability displacement ellipsoids. H atoms are shown as small spheres of arbitrary radii. (b) The crystal packing of (III), showing the I···O and N···O interactions [symmetry codes: (iii) 1/2 + x, 1/2 − y, 1/2 + z; (iv) 1/2 − x, 1/2 − y, −z; (v) 1/2 + x, 1/2 + y, z].
(II) 3-iodo-1-nitrobenzene top
Crystal data top
C6H4INO2F(000) = 232
Mr = 249.00Dx = 2.284 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 102 reflections
a = 5.977 (3) Åθ = 5.0–17.0°
b = 5.224 (3) ŵ = 4.36 mm1
c = 11.972 (6) ÅT = 213 K
β = 104.383 (10)°Needle, colourless
V = 362.1 (3) Å30.3 × 0.1 × 0.1 mm
Z = 2
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
1797 independent reflections
Radiation source: fine-focus sealed tube1584 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
ω scansθmax = 30.0°, θmin = 3.5°
Absorption correction: multi-scan
[SADABS (Sheldrick, 1996; Blessing, 1995)]
h = 87
Tmin = 0.599, Tmax = 0.647k = 77
2423 measured reflectionsl = 1614
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)] = 0.046H-atom parameters constrained
wR(F2) = 0.112 w = 1/[σ2(Fo2) + (0.0567P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
1797 reflectionsΔρmax = 1.94 e Å3
91 parametersΔρmin = 1.11 e Å3
1 restraintAbsolute structure: Flack (1983) and Bernardinelli & Flack (1985)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.09 (6)
Crystal data top
C6H4INO2V = 362.1 (3) Å3
Mr = 249.00Z = 2
Monoclinic, P21Mo Kα radiation
a = 5.977 (3) ŵ = 4.36 mm1
b = 5.224 (3) ÅT = 213 K
c = 11.972 (6) Å0.3 × 0.1 × 0.1 mm
β = 104.383 (10)°
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
1797 independent reflections
Absorption correction: multi-scan
[SADABS (Sheldrick, 1996; Blessing, 1995)]
1584 reflections with I > 2σ(I)
Tmin = 0.599, Tmax = 0.647Rint = 0.037
2423 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.112Δρmax = 1.94 e Å3
S = 1.03Δρmin = 1.11 e Å3
1797 reflectionsAbsolute structure: Flack (1983) and Bernardinelli & Flack (1985)
91 parametersAbsolute structure parameter: 0.09 (6)
1 restraint
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
I10.25586 (6)0.50925 (17)0.05533 (3)0.03788 (17)
C10.5878 (8)0.011 (3)0.3332 (4)0.0229 (9)
C40.7230 (12)0.4138 (14)0.2194 (6)0.0275 (13)
H4A0.76810.55310.18040.033*
O10.3066 (9)0.2671 (11)0.3634 (5)0.0370 (12)
N10.5096 (10)0.2027 (11)0.3933 (5)0.0260 (12)
C20.4248 (10)0.1243 (13)0.2443 (6)0.0242 (12)
H2A0.27110.06650.22370.029*
O20.6537 (10)0.3080 (11)0.4727 (5)0.0384 (12)
C30.4958 (11)0.3234 (14)0.1879 (6)0.0255 (13)
C50.8808 (11)0.2949 (15)0.3091 (7)0.0307 (15)
H5A1.03440.35320.33010.037*
C60.8153 (11)0.0909 (14)0.3685 (7)0.0289 (15)
H6A0.92080.01100.43000.035*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.0364 (2)0.0391 (2)0.0319 (2)0.0017 (3)0.00354 (15)0.0070 (3)
C10.024 (2)0.019 (2)0.025 (2)0.005 (4)0.0057 (19)0.002 (4)
C40.027 (3)0.030 (3)0.027 (3)0.006 (2)0.010 (3)0.002 (2)
O10.033 (2)0.033 (3)0.044 (3)0.013 (2)0.008 (2)0.001 (2)
N10.030 (3)0.020 (3)0.028 (3)0.001 (2)0.008 (2)0.000 (2)
C20.020 (3)0.025 (3)0.027 (3)0.001 (2)0.003 (2)0.002 (2)
O20.042 (3)0.031 (3)0.042 (3)0.005 (2)0.008 (3)0.009 (2)
C30.020 (3)0.034 (4)0.021 (3)0.008 (2)0.004 (2)0.002 (2)
C50.022 (3)0.031 (4)0.039 (4)0.007 (3)0.009 (3)0.005 (3)
C60.024 (3)0.032 (4)0.031 (4)0.003 (2)0.007 (3)0.003 (2)
Geometric parameters (Å, º) top
I1—C32.095 (7)O1—N11.224 (8)
C1—C21.385 (10)N1—O21.242 (8)
C1—C61.385 (9)C2—C31.364 (10)
C1—N11.465 (12)C2—H2A0.9400
C4—C51.388 (11)C5—C61.390 (11)
C4—C31.398 (9)C5—H5A0.9400
C4—H4A0.9400C6—H6A0.9400
C2—C1—C6123.7 (9)C1—C2—H2A121.2
C2—C1—N1117.0 (6)C2—C3—C4121.6 (6)
C6—C1—N1119.3 (6)C2—C3—I1119.4 (5)
C5—C4—C3119.1 (7)C4—C3—I1119.0 (5)
C5—C4—H4A120.5C4—C5—C6121.0 (6)
C3—C4—H4A120.5C4—C5—H5A119.5
O1—N1—O2123.4 (6)C6—C5—H5A119.5
O1—N1—C1118.6 (5)C1—C6—C5117.1 (7)
O2—N1—C1117.9 (5)C1—C6—H6A121.4
C3—C2—C1117.5 (7)C5—C6—H6A121.4
C3—C2—H2A121.2
(III) 3-iodo-1,5-dinitro-benzene top
Crystal data top
C6H3IN2O4F(000) = 1104
Mr = 294.00Dx = 2.309 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 53 reflections
a = 13.842 (9) Åθ = 3.4–17.6°
b = 8.164 (5) ŵ = 3.77 mm1
c = 15.288 (9) ÅT = 213 K
β = 101.766 (12)°Needle, colourless
V = 1691.2 (18) Å30.4 × 0.2 × 0.2 mm
Z = 8
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
2404 independent reflections
Radiation source: fine-focus sealed tube1927 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
ω scansθmax = 30.0°, θmin = 2.9°
Absorption correction: multi-scan
[SADABS (Sheldrick, 1996; Blessing, 1995)]
h = 1919
Tmin = 0.421, Tmax = 0.470k = 118
6318 measured reflectionsl = 2121
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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0103P)2 + 2.3695P]
where P = (Fo2 + 2Fc2)/3
2404 reflections(Δ/σ)max < 0.001
118 parametersΔρmax = 0.93 e Å3
0 restraintsΔρmin = 0.99 e Å3
Crystal data top
C6H3IN2O4V = 1691.2 (18) Å3
Mr = 294.00Z = 8
Monoclinic, C2/cMo Kα radiation
a = 13.842 (9) ŵ = 3.77 mm1
b = 8.164 (5) ÅT = 213 K
c = 15.288 (9) Å0.4 × 0.2 × 0.2 mm
β = 101.766 (12)°
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
2404 independent reflections
Absorption correction: multi-scan
[SADABS (Sheldrick, 1996; Blessing, 1995)]
1927 reflections with I > 2σ(I)
Tmin = 0.421, Tmax = 0.470Rint = 0.042
6318 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.084H-atom parameters constrained
S = 1.07Δρmax = 0.93 e Å3
2404 reflectionsΔρmin = 0.99 e Å3
118 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
I10.100566 (19)0.80925 (3)0.380331 (14)0.03627 (11)
O10.1019 (3)0.6800 (4)0.80264 (19)0.0559 (9)
C10.1186 (3)0.6743 (4)0.6559 (2)0.0287 (7)
C20.1089 (3)0.7634 (4)0.5773 (2)0.0270 (7)
H2A0.09800.87710.57630.032*
C30.1158 (3)0.6784 (4)0.5002 (2)0.0259 (7)
N10.1096 (3)0.7627 (5)0.7376 (2)0.0435 (9)
C60.1357 (3)0.5090 (5)0.6610 (2)0.0304 (8)
H6A0.14220.45130.71510.036*
O30.1861 (3)0.1901 (4)0.6581 (3)0.0648 (11)
C40.1326 (3)0.5120 (5)0.5017 (2)0.0295 (7)
H4A0.13700.45470.44930.035*
O20.1094 (4)0.9105 (5)0.7352 (2)0.0717 (12)
N20.1617 (3)0.2547 (5)0.5853 (3)0.0412 (8)
C50.1427 (3)0.4324 (4)0.5828 (2)0.0294 (7)
O40.1494 (4)0.1813 (4)0.5149 (3)0.0734 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.04522 (17)0.04186 (17)0.02156 (12)0.00267 (12)0.00645 (10)0.00836 (9)
O10.070 (2)0.077 (3)0.0245 (13)0.0093 (19)0.0184 (14)0.0080 (13)
C10.0337 (18)0.035 (2)0.0190 (14)0.0019 (16)0.0084 (13)0.0003 (12)
C20.0361 (19)0.0202 (16)0.0265 (15)0.0005 (15)0.0110 (14)0.0029 (12)
C30.0287 (16)0.0291 (18)0.0202 (14)0.0019 (15)0.0057 (12)0.0030 (12)
N10.060 (2)0.052 (2)0.0208 (14)0.001 (2)0.0134 (15)0.0031 (14)
C60.0321 (18)0.0319 (19)0.0276 (16)0.0008 (16)0.0069 (14)0.0098 (13)
O30.083 (3)0.0376 (19)0.070 (2)0.0053 (19)0.006 (2)0.0210 (15)
C40.0335 (18)0.0285 (18)0.0272 (16)0.0010 (16)0.0078 (13)0.0034 (13)
O20.133 (4)0.044 (2)0.0466 (18)0.009 (2)0.040 (2)0.0178 (15)
N20.0399 (19)0.0253 (16)0.058 (2)0.0007 (16)0.0086 (16)0.0019 (16)
C50.0307 (17)0.0238 (17)0.0325 (17)0.0018 (16)0.0038 (13)0.0058 (13)
O40.118 (4)0.0310 (18)0.069 (3)0.008 (2)0.014 (2)0.0094 (15)
Geometric parameters (Å, º) top
I1—C32.094 (3)N1—O21.207 (6)
O1—N11.225 (5)C6—C51.370 (5)
C1—C61.370 (5)C6—H6A0.9400
C1—C21.388 (5)O3—N21.215 (5)
C1—N11.470 (5)C4—C51.383 (5)
C2—C31.388 (5)C4—H4A0.9400
C2—H2A0.9400N2—O41.213 (5)
C3—C41.377 (5)N2—C51.473 (5)
C6—C1—C2123.5 (3)C1—C6—C5116.2 (3)
C6—C1—N1118.6 (3)C1—C6—H6A121.9
C2—C1—N1117.9 (3)C5—C6—H6A121.9
C1—C2—C3117.5 (3)C3—C4—C5117.7 (3)
C1—C2—H2A121.3C3—C4—H4A121.2
C3—C2—H2A121.3C5—C4—H4A121.2
C4—C3—C2121.3 (3)O4—N2—O3124.1 (4)
C4—C3—I1120.3 (2)O4—N2—C5118.1 (4)
C2—C3—I1118.4 (3)O3—N2—C5117.7 (4)
O2—N1—O1125.1 (4)C6—C5—C4123.8 (3)
O2—N1—C1117.8 (3)C6—C5—N2118.1 (3)
O1—N1—C1117.1 (4)C4—C5—N2118.1 (3)

Experimental details

(II)(III)
Crystal data
Chemical formulaC6H4INO2C6H3IN2O4
Mr249.00294.00
Crystal system, space groupMonoclinic, P21Monoclinic, C2/c
Temperature (K)213213
a, b, c (Å)5.977 (3), 5.224 (3), 11.972 (6)13.842 (9), 8.164 (5), 15.288 (9)
β (°) 104.383 (10) 101.766 (12)
V3)362.1 (3)1691.2 (18)
Z28
Radiation typeMo KαMo Kα
µ (mm1)4.363.77
Crystal size (mm)0.3 × 0.1 × 0.10.4 × 0.2 × 0.2
Data collection
DiffractometerBruker SMART 1000 CCD area-detector
diffractometer
Bruker SMART 1000 CCD area-detector
diffractometer
Absorption correctionMulti-scan
[SADABS (Sheldrick, 1996; Blessing, 1995)]
Multi-scan
[SADABS (Sheldrick, 1996; Blessing, 1995)]
Tmin, Tmax0.599, 0.6470.421, 0.470
No. of measured, independent and
observed [I > 2σ(I)] reflections
2423, 1797, 1584 6318, 2404, 1927
Rint0.0370.042
(sin θ/λ)max1)0.7030.704
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.112, 1.03 0.037, 0.084, 1.07
No. of reflections17972404
No. of parameters91118
No. of restraints10
H-atom treatmentH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.94, 1.110.93, 0.99
Absolute structureFlack (1983) and Bernardinelli & Flack (1985)?
Absolute structure parameter0.09 (6)?

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXTL (Siemens, 1996), SHELXTL and ORTEPIII (Farrugia, 1997).

Selected geometric parameters (Å, º) for (II) top
I1—C32.095 (7)O1—N11.224 (8)
C1—N11.465 (12)N1—O21.242 (8)
C2—C1—N1117.0 (6)O2—N1—C1117.9 (5)
C6—C1—N1119.3 (6)C2—C3—I1119.4 (5)
O1—N1—O2123.4 (6)C4—C3—I1119.0 (5)
O1—N1—C1118.6 (5)
Selected geometric parameters (Å, º) for (III) top
I1—C32.094 (3)O3—N21.215 (5)
O1—N11.225 (5)N2—O41.213 (5)
C1—N11.470 (5)N2—C51.473 (5)
N1—O21.207 (6)
C6—C1—N1118.6 (3)O1—N1—C1117.1 (4)
C2—C1—N1117.9 (3)O4—N2—O3124.1 (4)
C4—C3—I1120.3 (2)O4—N2—C5118.1 (4)
C2—C3—I1118.4 (3)O3—N2—C5117.7 (4)
O2—N1—O1125.1 (4)C6—C5—N2118.1 (3)
O2—N1—C1117.8 (3)C4—C5—N2118.1 (3)
 

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