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Molecules of 2-iodo-5-nitroaniline (I) are linked by N—H...O hydrogen bonds into centrosymmetric dimers and by asymmetric three-centre iodo...nitro interactions into chains, so forming chains of fused centrosymmetric rings: these chains are linked by aromatic π...π stacking interactions to form a three-dimensional structure. In the isomeric 4-iodo-2-nitro­aniline (II), each of the two independent molecules forms hydrogen-bonded chains that are linked by two-centre iodo...nitro interactions into sheets of two types, each containing only a single type of molecule: π...π stacking interactions are absent. In 2,4-diiodo-3-nitroaniline (III), where the nitro group is almost orthogonal to the aryl ring, a combination of N—H...O hydrogen bonds and two distinct two-centre iodo...nitro interactions links the molecules into a three-dimensional framework that is reinforced by aromatic π...π stacking interactions. Bond lengths and conformations are discussed and comparisons are drawn with related compounds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768102007978/na0135sup1.cif
Contains datablocks global, I, II, III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768102007978/na0135Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768102007978/na0135IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768102007978/na0135IIIsup4.hkl
Contains datablock III

CCDC references: 193585; 193586; 193587

Comment top

In full text version

Experimental top

In full text version

Refinement top

In full text version

Structure description top

In full text version

Computing details top

Data collection: SMART (Bruker, 1997) for (I); Kappa-CCD server software (Nonius, 1997) for (II), (III). Cell refinement: SMART (Bruker, 1997) for (I); DENZO-SMN (Otwinowski & Minor, 1997) for (II), (III). Data reduction: SHELXTL (Bruker, 1997) for (I); DENZO-SMN (Otwinowski & Minor, 1997) for (II), (III). 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 (Sheldrick, 1997) and PRPKAPPA (Ferguson, 1999).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
[Figure 8]
[Figure 9]
[Figure 10]
In full text version
(I) 2-Iodo-5-nitro-aniline top
Crystal data top
C6H5IN2O2Z = 2
Mr = 264.02F(000) = 248
Triclinic, P1Dx = 2.326 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.4236 (15) ÅCell parameters from 1674 reflections
b = 7.4979 (18) Åθ = 2.6–28.4°
c = 8.293 (2) ŵ = 4.20 mm1
α = 71.422 (4)°T = 120 K
β = 85.285 (4)°Plate, orange
γ = 86.125 (4)°0.24 × 0.12 × 0.04 mm
V = 376.98 (16) Å3
Data collection top
Kappa-CCD
diffractometer
1674 independent reflections
Radiation source: fine-focus sealed X-ray tube1620 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
φ scans, and ω scans with κ offsetsθmax = 28.4°, θmin = 2.6°
Absorption correction: multi-scan
SADABS (Bruker, 1997)
h = 87
Tmin = 0.434, Tmax = 0.850k = 109
2274 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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0823P)2 + 0.6322P]
where P = (Fo2 + 2Fc2)/3
1674 reflections(Δ/σ)max = 0.001
100 parametersΔρmax = 1.29 e Å3
0 restraintsΔρmin = 1.86 e Å3
Crystal data top
C6H5IN2O2γ = 86.125 (4)°
Mr = 264.02V = 376.98 (16) Å3
Triclinic, P1Z = 2
a = 6.4236 (15) ÅMo Kα radiation
b = 7.4979 (18) ŵ = 4.20 mm1
c = 8.293 (2) ÅT = 120 K
α = 71.422 (4)°0.24 × 0.12 × 0.04 mm
β = 85.285 (4)°
Data collection top
Kappa-CCD
diffractometer
1674 independent reflections
Absorption correction: multi-scan
SADABS (Bruker, 1997)
1620 reflections with I > 2σ(I)
Tmin = 0.434, Tmax = 0.850Rint = 0.025
2274 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.102H-atom parameters constrained
S = 1.07Δρmax = 1.29 e Å3
1674 reflectionsΔρmin = 1.86 e Å3
100 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.4449 (7)0.3288 (6)0.3513 (6)0.0159 (8)
N10.3913 (6)0.4158 (6)0.1884 (5)0.0219 (8)
C20.6412 (7)0.2368 (6)0.3906 (6)0.0173 (8)
I20.85816 (4)0.22346 (3)0.19084 (3)0.01932 (15)
C30.6972 (7)0.1579 (6)0.5580 (6)0.0204 (9)
C40.5607 (7)0.1669 (6)0.6939 (6)0.0200 (8)
C50.3661 (7)0.2556 (6)0.6540 (6)0.0176 (8)
N50.2134 (7)0.2636 (5)0.7936 (5)0.0205 (8)
O510.0377 (6)0.3326 (6)0.7592 (5)0.0282 (8)
O520.2667 (6)0.1987 (6)0.9413 (4)0.0283 (8)
C60.3051 (7)0.3348 (6)0.4907 (6)0.0180 (8)
H1A0.48120.41600.10240.026*
H1B0.26680.47190.16920.026*
H30.83120.09680.57950.025*
H40.59820.11500.80860.024*
H60.16960.39340.47140.022*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.018 (2)0.0155 (19)0.0126 (19)0.0095 (15)0.0021 (16)0.0016 (15)
N10.0179 (17)0.029 (2)0.0154 (17)0.0018 (15)0.0001 (14)0.0024 (15)
C20.0178 (19)0.0142 (18)0.019 (2)0.0031 (15)0.0049 (16)0.0055 (15)
I20.0192 (2)0.0186 (2)0.0180 (2)0.00292 (12)0.00588 (13)0.00399 (14)
C30.019 (2)0.019 (2)0.021 (2)0.0011 (16)0.0005 (18)0.0029 (17)
C40.023 (2)0.020 (2)0.015 (2)0.0029 (16)0.0009 (17)0.0016 (16)
C50.022 (2)0.0138 (17)0.0153 (18)0.0068 (15)0.0061 (15)0.0029 (15)
N50.029 (2)0.0177 (18)0.0151 (18)0.0066 (14)0.0046 (15)0.0052 (15)
O510.0228 (17)0.035 (2)0.0239 (19)0.0037 (15)0.0051 (15)0.0083 (16)
O520.036 (2)0.036 (2)0.0109 (16)0.0048 (16)0.0040 (14)0.0048 (14)
C60.020 (2)0.0171 (19)0.016 (2)0.0039 (16)0.0027 (16)0.0040 (15)
Geometric parameters (Å, º) top
C1—C21.406 (6)N5—O511.226 (6)
C2—C31.392 (6)N5—O521.233 (5)
C3—C41.387 (7)C2—I22.099 (4)
C4—C51.389 (6)N1—H1A0.8800
C5—C61.372 (6)N1—H1B0.8800
C6—C11.415 (6)C3—H30.9500
C1—N11.361 (6)C4—H40.9500
C5—N51.469 (6)C6—H60.9500
N1—C1—C2122.8 (4)C3—C4—C5116.6 (4)
N1—C1—C6120.4 (4)C3—C4—H4121.7
C2—C1—C6116.7 (4)C5—C4—H4121.7
C1—N1—H1A120.0C6—C5—C4124.0 (4)
C1—N1—H1B120.0C6—C5—N5117.3 (4)
H1A—N1—H1B120.0C4—C5—N5118.7 (4)
C3—C2—C1121.9 (4)O51—N5—O52122.6 (5)
C3—C2—I2119.1 (3)O51—N5—C5118.9 (4)
C1—C2—I2119.0 (3)O52—N5—C5118.5 (4)
C4—C3—C2121.1 (4)C5—C6—C1119.7 (4)
C4—C3—H3119.5C5—C6—H6120.1
C2—C3—H3119.5C1—C6—H6120.1
C4—C5—N5—O51176.1 (5)C6—C5—N5—O513.0 (7)
C4—C5—N5—O523.2 (7)C6—C5—N5—O52177.7 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···I20.882.763.237 (4)115
N1—H1A···N1i0.882.443.212 (6)147
N1—H1B···O51ii0.882.513.311 (6)152
Symmetry codes: (i) x+1, y+1, z; (ii) x, y+1, z+1.
(II) 4-Iodo-2-nitroaniline top
Crystal data top
C6H5IN2O2F(000) = 1984
Mr = 264.02Dx = 2.325 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 3426 reflections
a = 26.5541 (9) Åθ = 3.0–27.5°
b = 7.0445 (2) ŵ = 4.19 mm1
c = 16.4416 (5) ÅT = 120 K
β = 101.1548 (16)°Plate, orange
V = 3017.47 (16) Å30.25 × 0.20 × 0.05 mm
Z = 16
Data collection top
Kappa-CCD
diffractometer
3426 independent reflections
Radiation source: fine-focus sealed X-ray tube2696 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.056
φ scans, and ω scans with κ offsetsθmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
h = 3433
Tmin = 0.380, Tmax = 0.811k = 89
10470 measured reflectionsl = 2121
Refinement top
Refinement on F2Primary atom site location: Patterson
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0372P)2 + 3.2146P]
where P = (Fo2 + 2Fc2)/3
3426 reflections(Δ/σ)max = 0.001
193 parametersΔρmax = 1.22 e Å3
0 restraintsΔρmin = 1.55 e Å3
Crystal data top
C6H5IN2O2V = 3017.47 (16) Å3
Mr = 264.02Z = 16
Monoclinic, C2/cMo Kα radiation
a = 26.5541 (9) ŵ = 4.19 mm1
b = 7.0445 (2) ÅT = 120 K
c = 16.4416 (5) Å0.25 × 0.20 × 0.05 mm
β = 101.1548 (16)°
Data collection top
Kappa-CCD
diffractometer
3426 independent reflections
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
2696 reflections with I > 2σ(I)
Tmin = 0.380, Tmax = 0.811Rint = 0.056
10470 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0320 restraints
wR(F2) = 0.082H-atom parameters constrained
S = 1.05Δρmax = 1.22 e Å3
3426 reflectionsΔρmin = 1.55 e Å3
193 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
N110.68796 (13)0.1809 (5)0.1364 (2)0.0198 (8)
C110.68831 (15)0.0538 (5)0.0754 (2)0.0119 (8)
C120.68395 (15)0.1455 (5)0.0880 (2)0.0124 (8)
N120.67958 (13)0.2279 (4)0.16873 (18)0.0153 (7)
O110.68253 (14)0.4017 (4)0.17493 (18)0.0258 (8)
O120.67287 (12)0.1245 (3)0.23131 (16)0.0188 (7)
C130.68352 (15)0.2708 (5)0.0221 (2)0.0120 (8)
C140.68856 (15)0.2026 (5)0.0571 (2)0.0133 (8)
I140.685502 (10)0.39196 (3)0.154272 (15)0.01541 (10)
C150.69470 (15)0.0077 (5)0.0717 (2)0.0130 (6)
C160.69464 (16)0.1149 (5)0.0072 (2)0.0134 (9)
N210.56163 (13)0.1718 (5)0.71651 (19)0.0189 (8)
C210.56160 (16)0.0452 (6)0.6553 (2)0.0137 (8)
C220.56084 (16)0.1527 (5)0.6649 (2)0.0130 (8)
N220.56014 (13)0.2378 (4)0.74340 (18)0.0158 (7)
O210.56090 (14)0.4123 (4)0.74901 (17)0.0278 (8)
O220.55858 (12)0.1370 (4)0.80485 (16)0.0191 (7)
C230.56147 (14)0.2773 (5)0.5981 (2)0.0125 (8)
C240.56281 (15)0.2051 (5)0.5220 (2)0.0120 (8)
I240.562716 (10)0.39239 (3)0.422623 (14)0.01538 (10)
C250.56393 (15)0.0091 (5)0.5095 (2)0.0130 (6)
C260.56319 (16)0.1112 (5)0.5744 (2)0.0134 (9)
H11A0.69170.30250.12450.024*
H11B0.68400.14260.18820.024*
H130.67970.40330.03230.014*
H150.69890.03980.12660.016*
H160.69900.24660.01880.016*
H21A0.56210.29420.70600.023*
H21B0.56110.13220.76710.023*
H230.56100.41080.60620.015*
H250.56520.04030.45620.016*
H260.56380.24420.56500.016*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N110.037 (2)0.0105 (16)0.0134 (17)0.0012 (15)0.0078 (16)0.0014 (14)
C110.020 (2)0.0088 (18)0.0087 (18)0.0004 (16)0.0071 (16)0.0033 (15)
C120.017 (2)0.014 (2)0.0070 (18)0.0009 (15)0.0042 (15)0.0018 (15)
N120.023 (2)0.0151 (18)0.0080 (16)0.0010 (14)0.0039 (14)0.0004 (13)
O110.054 (2)0.0094 (15)0.0140 (15)0.0014 (13)0.0078 (15)0.0025 (12)
O120.0311 (18)0.0186 (15)0.0069 (13)0.0003 (12)0.0042 (12)0.0022 (11)
C130.017 (2)0.0091 (18)0.0102 (18)0.0006 (15)0.0024 (15)0.0022 (15)
C140.019 (2)0.014 (2)0.0074 (18)0.0022 (16)0.0036 (16)0.0034 (15)
I140.02537 (19)0.01421 (16)0.00771 (15)0.00093 (10)0.00583 (12)0.00265 (9)
C150.0202 (16)0.0138 (15)0.0062 (13)0.0003 (11)0.0056 (11)0.0003 (11)
C160.018 (2)0.0072 (19)0.016 (2)0.0005 (15)0.0057 (17)0.0019 (16)
N210.039 (2)0.0094 (15)0.0096 (16)0.0020 (16)0.0078 (15)0.0029 (14)
C210.020 (2)0.0130 (18)0.0092 (19)0.0015 (17)0.0043 (16)0.0017 (16)
C220.021 (2)0.0091 (17)0.0094 (18)0.0004 (16)0.0037 (16)0.0021 (15)
N220.028 (2)0.0099 (16)0.0097 (16)0.0020 (14)0.0045 (14)0.0007 (13)
O210.068 (3)0.0078 (14)0.0084 (14)0.0022 (14)0.0108 (15)0.0024 (11)
O220.0351 (19)0.0162 (15)0.0070 (14)0.0010 (12)0.0068 (13)0.0043 (11)
C230.017 (2)0.0100 (19)0.0108 (19)0.0022 (15)0.0028 (16)0.0002 (15)
C240.018 (2)0.0103 (19)0.0081 (18)0.0004 (15)0.0034 (15)0.0031 (14)
I240.02791 (19)0.01243 (16)0.00651 (15)0.00078 (10)0.00514 (12)0.00251 (9)
C250.0202 (16)0.0138 (15)0.0062 (13)0.0003 (11)0.0056 (11)0.0003 (11)
C260.021 (2)0.0096 (19)0.010 (2)0.0011 (16)0.0046 (17)0.0012 (15)
Geometric parameters (Å, º) top
C11—C121.421 (5)C21—C221.404 (5)
C12—C131.399 (5)C22—C231.409 (5)
C13—C141.370 (5)C23—C241.357 (5)
C14—C151.398 (5)C24—C251.397 (5)
C15—C161.366 (5)C25—C261.366 (5)
C16—C111.405 (5)C26—C211.417 (6)
C11—N111.343 (5)C21—N211.344 (5)
C12—N121.433 (5)C22—N221.426 (5)
N12—O111.232 (4)N22—O211.233 (4)
N12—O121.245 (4)N22—O221.242 (4)
C14—I142.095 (4)C24—I242.099 (4)
N11—H11A0.8800N21—H21A0.8800
N11—H11B0.8800N21—H21B0.8800
C13—H130.9500C23—H230.9500
C15—H150.9500C25—H250.9500
C16—H160.9500C26—H260.9500
C11—N11—H11A120.0C21—N21—H21A120.0
C11—N11—H11B120.0C21—N21—H21B120.0
H11A—N11—H11B120.0H21A—N21—H21B120.0
N11—C11—C12124.2 (4)N21—C21—C22124.9 (4)
N11—C11—C16120.0 (4)N21—C21—C26119.3 (4)
C12—C11—C16115.8 (3)C22—C21—C26115.8 (3)
C13—C12—C11121.6 (3)C21—C22—C23121.9 (3)
C13—C12—N12116.8 (3)C21—C22—N22121.5 (3)
C11—C12—N12121.6 (3)C23—C22—N22116.6 (3)
O11—N12—O12120.9 (3)O21—N22—O22120.8 (3)
O11—N12—C12118.9 (3)O21—N22—C22118.9 (3)
O12—N12—C12120.1 (3)O22—N22—C22120.2 (3)
C14—C13—C12120.0 (3)C24—C23—C22119.5 (3)
C14—C13—H13120.0C24—C23—H23120.3
C12—C13—H13120.0C22—C23—H23120.3
C13—C14—C15119.6 (3)C23—C24—C25120.7 (3)
C13—C14—I14119.4 (3)C23—C24—I24119.0 (3)
C15—C14—I14121.0 (2)C25—C24—I24120.3 (3)
C16—C15—C14120.3 (3)C26—C25—C24119.7 (3)
C16—C15—H15119.8C26—C25—H25120.2
C14—C15—H15119.8C24—C25—H25120.2
C15—C16—C11122.6 (3)C25—C26—C21122.5 (3)
C15—C16—H16118.7C25—C26—H26118.8
C11—C16—H16118.7C21—C26—H26118.8
C11—C12—N12—O11170.8 (4)C21—C22—N22—O21178.0 (4)
C11—C12—N12—O129.3 (6)C21—C22—N22—O222.2 (6)
C13—C12—N12—O119.5 (6)C23—C22—N22—O211.1 (6)
C13—C12—N12—O12170.5 (4)C23—C22—N22—O22178.6 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H11A···O11i0.882.243.005 (5)146
N11—H11B···O120.882.012.642 (4)128
N21—H21A···O21i0.882.192.979 (5)149
N21—H21B···O220.882.002.626 (4)127
C25—H25···O22ii0.952.553.495 (4)172
Symmetry codes: (i) x, y+1, z; (ii) x, y, z1/2.
(III) 2,4-Diiodo-3-nitroaniline top
Crystal data top
C6H4I2N2O2F(000) = 704
Mr = 389.91Dx = 2.752 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2144 reflections
a = 7.6069 (3) Åθ = 3.2–27.5°
b = 12.5917 (4) ŵ = 6.65 mm1
c = 10.2546 (3) ÅT = 120 K
β = 106.6693 (16)°Plate, colourless
V = 940.95 (6) Å30.28 × 0.24 × 0.08 mm
Z = 4
Data collection top
Kappa-CCD
diffractometer
2144 independent reflections
Radiation source: fine-focus sealed X-ray tube1950 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.104
φ scans, and ω scans with κ offsetsθmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
h = 98
Tmin = 0.180, Tmax = 0.618k = 1416
8456 measured reflectionsl = 1313
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)] = 0.045H-atom parameters constrained
wR(F2) = 0.122 w = 1/[σ2(Fo2) + (0.0534P)2 + 3.8878P]
where P = (Fo2 + 2Fc2)/3
S = 1.13(Δ/σ)max = 0.001
2144 reflectionsΔρmax = 2.36 e Å3
110 parametersΔρmin = 2.26 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0044 (5)
Crystal data top
C6H4I2N2O2V = 940.95 (6) Å3
Mr = 389.91Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.6069 (3) ŵ = 6.65 mm1
b = 12.5917 (4) ÅT = 120 K
c = 10.2546 (3) Å0.28 × 0.24 × 0.08 mm
β = 106.6693 (16)°
Data collection top
Kappa-CCD
diffractometer
2144 independent reflections
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
1950 reflections with I > 2σ(I)
Tmin = 0.180, Tmax = 0.618Rint = 0.104
8456 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.122H-atom parameters constrained
S = 1.13Δρmax = 2.36 e Å3
2144 reflectionsΔρmin = 2.26 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
N11.1845 (9)0.7118 (4)1.0887 (5)0.0243 (12)
C11.0924 (10)0.6510 (5)0.9783 (6)0.0196 (12)
C20.9004 (9)0.6434 (4)0.9321 (6)0.0181 (12)
I20.74257 (6)0.72632 (3)1.03612 (4)0.02391 (19)
C30.8187 (9)0.5795 (4)0.8200 (5)0.0140 (11)
N30.6156 (8)0.5717 (4)0.7755 (5)0.0193 (11)
O1310.5473 (7)0.4924 (4)0.8106 (5)0.0272 (10)
O1320.5278 (7)0.6435 (4)0.7058 (5)0.0256 (10)
C40.9182 (9)0.5253 (4)0.7479 (5)0.0174 (12)
I40.79798 (6)0.42775 (3)0.58144 (4)0.02460 (19)
C51.1090 (9)0.5363 (5)0.7901 (6)0.0198 (12)
C61.1913 (9)0.5982 (5)0.9006 (6)0.0198 (12)
H1A1.12260.74821.13410.029*
H1B1.30520.71411.11380.029*
H51.18170.50090.74210.024*
H61.32100.60590.92610.024*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.028 (3)0.023 (3)0.019 (2)0.004 (2)0.001 (2)0.001 (2)
C10.030 (3)0.013 (2)0.015 (2)0.002 (2)0.006 (2)0.004 (2)
C20.026 (3)0.010 (2)0.017 (3)0.001 (2)0.005 (2)0.000 (2)
I20.0295 (3)0.0187 (3)0.0244 (3)0.00087 (15)0.0092 (2)0.00817 (15)
C30.017 (3)0.010 (2)0.014 (2)0.0006 (19)0.003 (2)0.0049 (19)
N30.026 (3)0.014 (2)0.018 (2)0.001 (2)0.006 (2)0.0029 (18)
O1310.025 (3)0.025 (2)0.034 (2)0.005 (2)0.011 (2)0.0041 (19)
O1320.023 (2)0.023 (2)0.027 (2)0.0044 (19)0.0006 (19)0.0063 (18)
C40.027 (3)0.012 (3)0.013 (2)0.000 (2)0.007 (2)0.001 (2)
I40.0378 (3)0.0208 (3)0.0164 (3)0.00668 (16)0.0098 (2)0.00600 (14)
C50.023 (3)0.020 (3)0.017 (3)0.004 (2)0.008 (2)0.002 (2)
C60.016 (3)0.024 (3)0.020 (3)0.003 (2)0.006 (2)0.003 (2)
Geometric parameters (Å, º) top
N1—H1A0.8800C1—N11.380 (8)
N1—H1B0.8800C2—I22.099 (6)
C1—C21.404 (10)C3—N31.484 (8)
C2—C31.394 (8)N3—O1311.225 (7)
C3—C41.380 (8)N3—O1321.225 (7)
C4—C51.398 (9)C4—I42.089 (6)
C5—C61.370 (9)C5—H50.9500
C6—C11.409 (9)C6—H60.9500
C1—N1—H1A120.0O132—N3—O131124.5 (6)
C1—N1—H1B120.0O132—N3—C3118.4 (5)
H1A—N1—H1B120.0O131—N3—C3117.1 (5)
N1—C1—C2123.4 (6)C3—C4—C5117.7 (5)
N1—C1—C6119.8 (6)C3—C4—I4123.4 (5)
C2—C1—C6116.7 (6)C5—C4—I4118.9 (4)
C3—C2—C1119.5 (6)C6—C5—C4120.0 (6)
C3—C2—I2121.4 (5)C6—C5—H5120.0
C1—C2—I2119.1 (4)C4—C5—H5120.0
C4—C3—C2122.9 (6)C5—C6—C1123.0 (6)
C4—C3—N3119.0 (5)C5—C6—H6118.5
C2—C3—N3118.0 (5)C1—C6—H6118.5
N1—C1—C2—C3179.6 (5)C2—C3—N3—O131100.3 (6)
C6—C1—C2—C34.4 (8)C2—C3—C4—C50.3 (8)
N1—C1—C2—I20.8 (8)N3—C3—C4—C5178.4 (5)
C6—C1—C2—I2176.8 (4)C2—C3—C4—I4179.2 (4)
C1—C2—C3—C42.4 (8)N3—C3—C4—I42.1 (7)
I2—C2—C3—C4178.9 (4)C3—C4—C5—C60.8 (9)
C1—C2—C3—N3178.9 (5)I4—C4—C5—C6178.7 (4)
I2—C2—C3—N30.1 (7)C4—C5—C6—C11.5 (9)
C4—C3—N3—O13298.4 (6)N1—C1—C6—C5179.8 (6)
C2—C3—N3—O13280.4 (7)C2—C1—C6—C54.1 (9)
C4—C3—N3—O13181.0 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···O132i0.882.463.128 (8)133
Symmetry code: (i) x+1, y+3/2, z+1/2.

Experimental details

(I)(II)(III)
Crystal data
Chemical formulaC6H5IN2O2C6H5IN2O2C6H4I2N2O2
Mr264.02264.02389.91
Crystal system, space groupTriclinic, P1Monoclinic, C2/cMonoclinic, P21/c
Temperature (K)120120120
a, b, c (Å)6.4236 (15), 7.4979 (18), 8.293 (2)26.5541 (9), 7.0445 (2), 16.4416 (5)7.6069 (3), 12.5917 (4), 10.2546 (3)
α, β, γ (°)71.422 (4), 85.285 (4), 86.125 (4)90, 101.1548 (16), 9090, 106.6693 (16), 90
V3)376.98 (16)3017.47 (16)940.95 (6)
Z2164
Radiation typeMo KαMo KαMo Kα
µ (mm1)4.204.196.65
Crystal size (mm)0.24 × 0.12 × 0.040.25 × 0.20 × 0.050.28 × 0.24 × 0.08
Data collection
DiffractometerKappa-CCDKappa-CCDKappa-CCD
Absorption correctionMulti-scan
SADABS (Bruker, 1997)
Multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
Multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
Tmin, Tmax0.434, 0.8500.380, 0.8110.180, 0.618
No. of measured, independent and
observed [I > 2σ(I)] reflections
2274, 1674, 1620 10470, 3426, 2696 8456, 2144, 1950
Rint0.0250.0560.104
(sin θ/λ)max1)0.6700.6490.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.102, 1.07 0.032, 0.082, 1.05 0.045, 0.122, 1.13
No. of reflections167434262144
No. of parameters100193110
H-atom treatmentH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.29, 1.861.22, 1.552.36, 2.26

Computer programs: SMART (Bruker, 1997), Kappa-CCD server software (Nonius, 1997), DENZO-SMN (Otwinowski & Minor, 1997), SHELXTL (Bruker, 1997), SHELXS97 (Sheldrick, 1997), PLATON (Spek, 2002), SHELXL97 (Sheldrick, 1997) and PRPKAPPA (Ferguson, 1999).

Selected geometric parameters (Å, º) for (I) top
C1—C21.406 (6)C1—N11.361 (6)
C2—C31.392 (6)C5—N51.469 (6)
C3—C41.387 (7)N5—O511.226 (6)
C4—C51.389 (6)N5—O521.233 (5)
C5—C61.372 (6)C2—I22.099 (4)
C6—C11.415 (6)
C4—C5—N5—O523.2 (7)C6—C5—N5—O513.0 (7)
Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···I20.882.763.237 (4)115
N1—H1A···N1i0.882.443.212 (6)147
N1—H1B···O51ii0.882.513.311 (6)152
Symmetry codes: (i) x+1, y+1, z; (ii) x, y+1, z+1.
Selected geometric parameters (Å, º) for (II) top
C11—C121.421 (5)C21—C221.404 (5)
C12—C131.399 (5)C22—C231.409 (5)
C13—C141.370 (5)C23—C241.357 (5)
C14—C151.398 (5)C24—C251.397 (5)
C15—C161.366 (5)C25—C261.366 (5)
C16—C111.405 (5)C26—C211.417 (6)
C11—N111.343 (5)C21—N211.344 (5)
C12—N121.433 (5)C22—N221.426 (5)
N12—O111.232 (4)N22—O211.233 (4)
N12—O121.245 (4)N22—O221.242 (4)
C14—I142.095 (4)C24—I242.099 (4)
N11—C11—C12124.2 (4)N21—C21—C22124.9 (4)
N11—C11—C16120.0 (4)N21—C21—C26119.3 (4)
C12—C11—C16115.8 (3)C22—C21—C26115.8 (3)
C11—C12—N12—O129.3 (6)C21—C22—N22—O222.2 (6)
C13—C12—N12—O119.5 (6)C23—C22—N22—O211.1 (6)
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
N11—H11A···O11i0.882.243.005 (5)146
N11—H11B···O120.882.012.642 (4)128
N21—H21A···O21i0.882.192.979 (5)149
N21—H21B···O220.882.002.626 (4)127
C25—H25···O22ii0.952.553.495 (4)172
Symmetry codes: (i) x, y+1, z; (ii) x, y, z1/2.
Selected geometric parameters (Å, º) for (III) top
C1—C21.404 (10)C1—N11.380 (8)
C2—C31.394 (8)C2—I22.099 (6)
C3—C41.380 (8)C3—N31.484 (8)
C4—C51.398 (9)N3—O1311.225 (7)
C5—C61.370 (9)N3—O1321.225 (7)
C6—C11.409 (9)C4—I42.089 (6)
N1—C1—C2123.4 (6)C4—C3—C2122.9 (6)
N1—C1—C6119.8 (6)C4—C3—N3119.0 (5)
C2—C1—C6116.7 (6)C2—C3—N3118.0 (5)
C3—C2—C1119.5 (6)C3—C4—C5117.7 (5)
C3—C2—I2121.4 (5)C3—C4—I4123.4 (5)
C1—C2—I2119.1 (4)C5—C4—I4118.9 (4)
C2—C3—N3—O13280.4 (7)C2—C3—N3—O131100.3 (6)
Hydrogen-bond geometry (Å, º) for (III) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···O132i0.882.463.128 (8)133
Symmetry code: (i) x+1, y+3/2, z+1/2.
 

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