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The title compounds, 4-(diiodo­arsanyl)benzoic acid, (I), and 3-(diiodo­arsanyl)benzoic acid, (II), both [As(C7H5O2)I2], which possess a -COOH coordinating group, form mol­ecular crystal structures composed of hydrogen-bonded dimers, the packing differences of which are caused by the relative position of the diiodo­arsan­yl groups. The para isomer, with Z' = 1, crystallizes in a layered structure with shortened contacts of the As atoms to only the arene rings of adjacent mol­ecules. In contrast, the meta isomer, with Z' = 3, forms separate recta­ngular blocks of three ribbons, each composed of dimeric mol­ecular units positioned almost directly above each other and with the As atoms possessing only two As...I contacts to the I atoms of neighbouring mol­ecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270112040000/sk3449sup1.cif
Contains datablocks I, II, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270112040000/sk3449Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270112040000/sk3449IIsup3.hkl
Contains datablock II

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270112040000/sk3449Isup4.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270112040000/sk3449IIsup5.cml
Supplementary material

cdx

Chemdraw file https://doi.org/10.1107/S0108270112040000/sk3449Isup6.cdx
Supplementary material

cdx

Chemdraw file https://doi.org/10.1107/S0108270112040000/sk3449IIsup7.cdx
Supplementary material

CCDC references: 914643; 914644

Comment top

Organoarsenic halogenides are easily accessible AsIII compounds of the type RnAsHal3-n (n = 1, 2) and are widely used for the preparation of various organoarsenic derivatives (Gross et al., 1997), including arsa-heterocycles (Matuska et al., 2010; Avtomonov et al., 1997), diarsenes (Twamley et al., 1999), organometallic complexes such as arsinidenes (Huttner & Evertz, 1986; Jutzi & Kroos, 1990) and cluster compounds (Song et al., 2001; Deck & Vahrenkamp, 1991; Deck et al., 1987). Iodine derivatives, with the I atoms as good leaving groups, have been shown to be particularly good reagents for introducing the RAs group into cluster complexes as a result of nucleophilic substitution reactions (Konchenko et al., 1999; Pushkarevsky et al., 2006; Winter et al., 1983; Ilyin et al., 2012). There are only three known structures of RAsI2 compounds, and in all three cases the As atom has additional contacts with the donor atoms of neighbouring groups or molecules. Thus, in the case of CH3AsI2, the As atom contacts the two I atoms of a neighbouring molecule, which determines the stacked arrangement of the molecules (Camerman & Trotter, 1963). In the other two structures, which have bulky substituents (R = pentamethyl or tetraisopropylcyclopentadienyl), the As atom has additional contacts with a double bond of the cyclopentadienyl (Cp) ring of the same molecule (Megges et al., 1996; Avtomonov et al., 1996). As a consequence, the As atom, hidden by the bulky substituent, has no additional contacts with the other molecules.

The structures of 4-(diiodoarsanyl)benzoic acid, (I) (Fig. 1), and 3-(diiodoarsanyl)benzoic acid, (II) (Fig. 2), have asymmetric units with one and three crystallographically independent molecules, respectively. The molecules of both compounds are dimerized by hydrogen bonding between the carboxylic acid groups. The acidic H atom in (II) is disordered over two positions with 0.5 occupancy. The dimer packings in (I) and (II) are different. The planar molecules in (I) are located parallel to each other to form infinite stacks (Fig. 3). Interestingly, the environment of the As atoms is completed by the arene ring of a neighbouring molecule [3.469 (5) Å], which resembles the known interactions in the molecules of Cp*-substituted (Cp* is pentamethylcyclopentadienyl) diiodoarsenides (Avtomonov et al., 1996). The aromatic rings are shifted apart, so there is no ππ stacking between them in (I). In contrast, the π systems of the aryl fragments in (II) are most probably bound by ππ interactions [the distances between the centres of the aryl rings are 3.967 (7) and 3.902 (7) Å, with the nearest rings almost fully overlapped]. Also in contrast with (I), each As atom is positioned close to the two I atoms of a neighbouring molecule, thus forming two contacts of 3.56 (9) Å (cf. 3.605 and 3.658 Å for CH3AsI2; Camerman & Trotter, 1963), noticeably shorter than the sum of the van der Waals radii of the elements (3.98 Å; Bondi, 1964; Fig. 4). Being sufficiently large, the I atoms make it impossible for the arene cycles to remain parallel, analogous to the structure of (I), so the rings are skewed with respect to the line of hydrogen bonding (Fig. 4). Such bending makes it possible for only three molecules to pack on top of each other, so infinite packing analogous to (I) is not possible. Consequently, the three dimeric units are translated to form bundles of three ribbons of different bending (Fig. 5). The bundles themselves form a parquet-like layered packing parallel to (101).

The different –AsI2 group position relative to neighbouring molecules causes the two packing modes. Consequently, the orientation of this group with respect to the arene ring is different: the I1—As1—C5—C4 torsion angle is 0.0 (5)° in (I), and the equivalent angles are 38.7 (3), 38.0 (3) and 36.3 (3)° in (II), while the I1—As1—I2 torsion angle for both compounds has nearly the same value [101.6 (11)°]. The average As—C bond lengths do not seem to depend on the position of the carboxylic acid group, viz. 1.977 (5) Å for (I) and 1.976 (5) Å for (II).

As a consequence of (II) having more evident interactions between the molecules in the crystal packing, namely ππ and As···I versus only As···C6 interactions in the packing of (I), the packing of isomer (II) is slightly denser than that of (I) (Dcalc = 2.843 and 2.789 Mg m-3, respectively).

Related literature top

For related literature, see: Avtomonov et al. (1996, 1997); Bondi (1964); Camerman & Trotter (1963); Deck & Vahrenkamp (1991); Deck et al. (1987); Gross et al. (1997); Huttner & Evertz (1986); Ilyin et al. (2012); Jutzi & Kroos (1990); Konchenko et al. (1999); Matuska et al. (2010); Megges et al. (1996); Pushkarevsky et al. (2006); Song et al. (2001); Twamley et al. (1999); Winter et al. (1983).

Experimental top

For the syntheses of arsonic acids [p- or m-HOOCC6H4AsO(OH)2], the corresponding aminobenzoic acids were diazotated in dilute HCl. The diazo solution was added dropwise to a solution containing NaAsO2 in the presence of excess KOH (Bart reaction). The mixture was heated for 30 min with activated coal and filtered. The mother solution was acidified with HCl and cooled. A crystalline powder of p- or m-HOOCC6H4AsO(OH)2 precipitated at pH 3. To obtain the iodide derivatives, p- or m-HOOCC6H4AsO(OH)2 was treated with excess NaI and Na2SO3 in aqueous solution. [Please give quantities or mole ratios, preferably for all steps but at the very least for this final step] Yellow precipitates of p- or m-HOOCC6H4AsI2 were filtered off, dried and recrystallized from chloroform–diethyl ether mixtures [Solvent ratios?].

Refinement top

For both compounds, H atoms were located in difference Fourier maps and subsequently positioned geometrically, with C—H = 0.93 and O—H = 0.82 Å. They were refined as riding, with Uiso(H) = 1.2Ueq(C,O). [Please check added text]

Computing details top

For both compounds, data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: DIAMOND (Bergerhoff et al., 1996); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. The asymmetric unit of (II), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 3] Fig. 3. The layered packing in the structure of (I).
[Figure 4] Fig. 4. A stack of three pairs of the dimers of (II), as part of the molecular ribbons, viewed along the a axis (the I atoms of neighbouring ribbons are marked with asterisks; the bending of the ribbons is schematically depicted by thick dashed lines).
[Figure 5] Fig. 5. Bundles of three ribbons in (II), forming parquet-like layered packing parallel to (101).
(I) 4-(Diiodoarsanyl)benzoic acid top
Crystal data top
[As(C7H5O2)I2]Z = 2
Mr = 449.83F(000) = 404
Triclinic, P1Dx = 2.789 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 4.8992 (2) ÅCell parameters from 2330 reflections
b = 8.4434 (5) Åθ = 2.5–28.2°
c = 13.6616 (9) ŵ = 8.90 mm1
α = 107.148 (2)°T = 296 K
β = 91.569 (2)°Prism, orange
γ = 96.376 (2)°0.35 × 0.20 × 0.18 mm
V = 535.59 (5) Å3
Data collection top
Bruker Nonius X8 APEXII CCD area-detector
diffractometer
2144 independent reflections
Radiation source: fine-focus sealed tube1859 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
Detector resolution: 25 pixels mm-1θmax = 26.4°, θmin = 2.5°
ϕ scansh = 46
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
k = 1010
Tmin = 0.147, Tmax = 0.297l = 1717
3909 measured reflections
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) = 0.109H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0622P)2 + 0.9538P]
where P = (Fo2 + 2Fc2)/3
2144 reflections(Δ/σ)max < 0.001
110 parametersΔρmax = 1.87 e Å3
0 restraintsΔρmin = 1.67 e Å3
Crystal data top
[As(C7H5O2)I2]γ = 96.376 (2)°
Mr = 449.83V = 535.59 (5) Å3
Triclinic, P1Z = 2
a = 4.8992 (2) ÅMo Kα radiation
b = 8.4434 (5) ŵ = 8.90 mm1
c = 13.6616 (9) ÅT = 296 K
α = 107.148 (2)°0.35 × 0.20 × 0.18 mm
β = 91.569 (2)°
Data collection top
Bruker Nonius X8 APEXII CCD area-detector
diffractometer
2144 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
1859 reflections with I > 2σ(I)
Tmin = 0.147, Tmax = 0.297Rint = 0.027
3909 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.109H-atom parameters constrained
S = 1.07Δρmax = 1.87 e Å3
2144 reflectionsΔρmin = 1.67 e Å3
110 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
I11.02638 (11)0.14239 (5)0.22256 (4)0.06112 (19)
I20.69106 (11)0.27248 (7)0.00248 (3)0.0675 (2)
As11.02783 (11)0.39534 (7)0.15666 (4)0.03714 (18)
O10.1103 (9)0.7967 (6)0.4937 (3)0.0499 (10)
H10.00010.86080.51950.060*
O20.2277 (9)0.9884 (5)0.4150 (3)0.0467 (10)
C10.2460 (11)0.8530 (7)0.4280 (4)0.0351 (11)
C20.4299 (10)0.7365 (6)0.3660 (4)0.0324 (11)
C30.4613 (12)0.5840 (7)0.3834 (4)0.0400 (12)
H30.36860.55330.43470.048*
C40.6327 (12)0.4782 (7)0.3231 (4)0.0404 (12)
H40.65490.37700.33460.048*
C50.7686 (10)0.5235 (6)0.2469 (4)0.0313 (10)
C60.7396 (11)0.6757 (7)0.2302 (4)0.0389 (12)
H60.83500.70640.17940.047*
C70.5689 (11)0.7821 (7)0.2891 (4)0.0365 (11)
H70.54770.88310.27710.044*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.0802 (4)0.0431 (3)0.0748 (3)0.0304 (2)0.0300 (3)0.0296 (2)
I20.0762 (4)0.0785 (4)0.0383 (3)0.0263 (3)0.0056 (2)0.0031 (2)
As10.0409 (3)0.0342 (3)0.0402 (3)0.0158 (2)0.0168 (2)0.0120 (2)
O10.059 (3)0.048 (2)0.049 (2)0.025 (2)0.024 (2)0.016 (2)
O20.056 (2)0.041 (2)0.046 (2)0.0245 (19)0.0165 (19)0.0098 (18)
C10.037 (3)0.040 (3)0.026 (2)0.012 (2)0.004 (2)0.004 (2)
C20.032 (2)0.034 (3)0.030 (2)0.012 (2)0.002 (2)0.004 (2)
C30.050 (3)0.041 (3)0.035 (3)0.020 (2)0.018 (2)0.015 (2)
C40.055 (3)0.037 (3)0.038 (3)0.020 (2)0.016 (2)0.017 (2)
C50.030 (2)0.032 (2)0.031 (2)0.0114 (19)0.0079 (19)0.003 (2)
C60.041 (3)0.038 (3)0.039 (3)0.012 (2)0.012 (2)0.012 (2)
C70.041 (3)0.031 (3)0.041 (3)0.010 (2)0.010 (2)0.013 (2)
Geometric parameters (Å, º) top
I1—As12.5501 (7)C3—C41.397 (7)
I2—As12.5726 (8)C3—H30.9300
As1—C51.977 (5)C4—C51.375 (7)
O1—C11.300 (7)C4—H40.9300
O1—H10.8200C5—C61.391 (8)
O2—C11.220 (7)C6—C71.389 (7)
C1—C21.498 (7)C6—H60.9300
C2—C71.392 (8)C7—H70.9300
C2—C31.400 (8)
C5—As1—I1101.11 (16)C5—C4—C3120.1 (5)
C5—As1—I296.83 (15)C5—C4—H4120.0
I1—As1—I2100.32 (3)C3—C4—H4120.0
C1—O1—H1109.5C4—C5—C6120.3 (5)
O2—C1—O1124.2 (5)C4—C5—As1126.3 (4)
O2—C1—C2121.1 (5)C6—C5—As1113.4 (4)
O1—C1—C2114.7 (5)C7—C6—C5120.4 (5)
C7—C2—C3120.0 (5)C7—C6—H6119.8
C7—C2—C1118.5 (5)C5—C6—H6119.8
C3—C2—C1121.5 (5)C6—C7—C2119.5 (5)
C4—C3—C2119.7 (5)C6—C7—H7120.2
C4—C3—H3120.2C2—C7—H7120.2
C2—C3—H3120.2
O2—C1—C2—C73.4 (8)I1—As1—C5—C40.0 (5)
O1—C1—C2—C7175.8 (5)I2—As1—C5—C4101.9 (5)
O2—C1—C2—C3177.2 (5)I1—As1—C5—C6177.2 (4)
O1—C1—C2—C33.6 (7)I2—As1—C5—C680.8 (4)
C7—C2—C3—C40.0 (8)C4—C5—C6—C71.2 (8)
C1—C2—C3—C4179.3 (5)As1—C5—C6—C7178.7 (4)
C2—C3—C4—C50.3 (9)C5—C6—C7—C20.9 (8)
C3—C4—C5—C60.9 (9)C3—C2—C7—C60.3 (8)
C3—C4—C5—As1178.0 (4)C1—C2—C7—C6179.7 (5)
(II) 3-(Diiodoarsanyl)benzoic acid top
Crystal data top
[As(C7H5O2)I2]F(000) = 2424
Mr = 449.83Dx = 2.843 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 9956 reflections
a = 7.6751 (5) Åθ = 2.8–27.5°
b = 18.6142 (12) ŵ = 9.07 mm1
c = 22.0692 (12) ÅT = 296 K
β = 90.206 (2)°Plate, orange
V = 3152.9 (3) Å30.18 × 0.15 × 0.06 mm
Z = 12
Data collection top
Bruker Nonius X8 APEX CCD area-detector
diffractometer
5996 independent reflections
Radiation source: fine-focus sealed tube5277 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
Detector resolution: 25 pixels mm-1θmax = 25.7°, θmin = 2.4°
ϕ scansh = 99
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
k = 2222
Tmin = 0.292, Tmax = 0.612l = 1726
23397 measured reflections
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)] = 0.021Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.046H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0089P)2 + 4.041P]
where P = (Fo2 + 2Fc2)/3
5996 reflections(Δ/σ)max = 0.001
325 parametersΔρmax = 0.88 e Å3
0 restraintsΔρmin = 0.78 e Å3
Crystal data top
[As(C7H5O2)I2]V = 3152.9 (3) Å3
Mr = 449.83Z = 12
Monoclinic, P21/nMo Kα radiation
a = 7.6751 (5) ŵ = 9.07 mm1
b = 18.6142 (12) ÅT = 296 K
c = 22.0692 (12) Å0.18 × 0.15 × 0.06 mm
β = 90.206 (2)°
Data collection top
Bruker Nonius X8 APEX CCD area-detector
diffractometer
5996 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
5277 reflections with I > 2σ(I)
Tmin = 0.292, Tmax = 0.612Rint = 0.033
23397 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0210 restraints
wR(F2) = 0.046H-atom parameters constrained
S = 1.04Δρmax = 0.88 e Å3
5996 reflectionsΔρmin = 0.78 e Å3
325 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*/UeqOcc. (<1)
I110.33036 (3)0.344090 (14)0.404221 (11)0.04052 (7)
I120.16707 (3)0.355612 (15)0.343524 (11)0.04430 (7)
I210.65172 (3)0.077740 (15)0.095365 (11)0.04173 (7)
I220.16121 (3)0.062395 (16)0.035467 (11)0.04637 (7)
I310.49621 (3)0.226146 (15)0.243134 (11)0.04468 (7)
I320.00493 (3)0.220330 (17)0.183977 (12)0.05156 (8)
As10.01740 (5)0.371427 (19)0.441333 (16)0.03251 (8)
As20.33939 (4)0.118495 (19)0.123774 (15)0.03020 (8)
As30.18184 (5)0.25492 (2)0.278397 (17)0.03654 (9)
O110.3286 (3)0.15495 (16)0.57083 (12)0.0498 (7)
H110.39030.13010.59280.060*0.50
O120.1199 (4)0.09822 (16)0.62175 (13)0.0542 (8)
H11A0.20550.07990.63790.065*0.50
O210.6500 (3)0.03724 (17)0.30615 (12)0.0542 (8)
H210.71100.05470.33290.065*0.50
O220.4407 (4)0.08732 (17)0.36147 (13)0.0564 (8)
H21A0.52520.09920.38200.068*0.50
O310.4965 (4)0.06411 (16)0.43918 (13)0.0542 (8)
H310.55550.04140.46360.065*0.50
O320.2828 (4)0.00745 (16)0.48789 (13)0.0532 (7)
H31A0.36660.00880.50660.064*0.50
C110.0392 (4)0.27807 (19)0.47918 (14)0.0315 (7)
C120.0860 (4)0.24050 (18)0.51161 (14)0.0314 (7)
H120.20250.25410.50960.038*
C130.0364 (5)0.18234 (19)0.54720 (15)0.0327 (8)
C140.1379 (5)0.1618 (2)0.55058 (17)0.0435 (9)
H140.17090.12320.57480.052*
C150.2609 (5)0.1991 (2)0.51761 (18)0.0484 (10)
H150.37750.18570.51950.058*
C160.2119 (5)0.2567 (2)0.48159 (17)0.0413 (9)
H160.29540.28110.45890.050*
C170.1685 (5)0.1425 (2)0.58238 (15)0.0353 (8)
C210.2835 (4)0.04487 (19)0.18495 (14)0.0307 (7)
C220.4074 (4)0.02018 (18)0.22551 (15)0.0320 (7)
H220.52350.03350.22110.038*
C230.3585 (5)0.02474 (19)0.27318 (15)0.0333 (8)
C240.1853 (5)0.0447 (2)0.27951 (17)0.0416 (9)
H240.15240.07450.31130.050*
C250.0623 (5)0.0205 (2)0.23904 (18)0.0472 (10)
H250.05340.03450.24310.057*
C260.1103 (5)0.0245 (2)0.19234 (16)0.0396 (9)
H260.02600.04140.16550.048*
C270.4911 (5)0.0517 (2)0.31641 (16)0.0369 (8)
C310.1308 (5)0.1701 (2)0.32930 (16)0.0361 (8)
C320.2564 (5)0.13725 (19)0.36535 (15)0.0354 (8)
H320.37330.14930.36110.043*
C330.2059 (5)0.08604 (19)0.40811 (16)0.0357 (8)
C340.0297 (5)0.0680 (2)0.41381 (18)0.0449 (9)
H340.00460.03410.44230.054*
C350.0926 (5)0.1002 (2)0.37735 (19)0.0507 (10)
H350.20940.08750.38080.061*
C360.0430 (5)0.1514 (2)0.33554 (18)0.0443 (9)
H360.12680.17350.31140.053*
C370.3357 (5)0.0502 (2)0.44754 (17)0.0403 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I110.02972 (12)0.04592 (15)0.04591 (14)0.00576 (10)0.00118 (10)0.00079 (11)
I120.03793 (14)0.05514 (17)0.03978 (13)0.00256 (11)0.00776 (11)0.00523 (12)
I210.02828 (12)0.05637 (17)0.04055 (13)0.00474 (11)0.00394 (10)0.00832 (11)
I220.04183 (14)0.06285 (18)0.03435 (13)0.01505 (12)0.00812 (11)0.00167 (11)
I310.03035 (13)0.05791 (17)0.04580 (14)0.00640 (11)0.00149 (11)0.00333 (12)
I320.03820 (15)0.0703 (2)0.04614 (15)0.01008 (13)0.00749 (12)0.00136 (13)
As10.03224 (19)0.03094 (19)0.03433 (18)0.00017 (15)0.00066 (15)0.00144 (15)
As20.02696 (17)0.03394 (19)0.02969 (17)0.00064 (14)0.00093 (14)0.00141 (15)
As30.0348 (2)0.0358 (2)0.0390 (2)0.00053 (16)0.00310 (16)0.00025 (16)
O110.0323 (14)0.0619 (19)0.0553 (17)0.0036 (13)0.0003 (12)0.0238 (14)
O120.0418 (16)0.065 (2)0.0554 (17)0.0057 (14)0.0014 (13)0.0323 (15)
O210.0363 (15)0.079 (2)0.0476 (16)0.0034 (14)0.0006 (12)0.0275 (15)
O220.0438 (16)0.071 (2)0.0540 (17)0.0059 (15)0.0102 (13)0.0331 (16)
O310.0388 (16)0.066 (2)0.0578 (17)0.0040 (14)0.0036 (13)0.0210 (15)
O320.0490 (17)0.0582 (19)0.0524 (16)0.0056 (14)0.0061 (13)0.0208 (14)
C110.0316 (18)0.0342 (19)0.0289 (17)0.0016 (15)0.0013 (14)0.0022 (14)
C120.0281 (18)0.0329 (19)0.0331 (17)0.0043 (14)0.0024 (14)0.0015 (15)
C130.0338 (19)0.0338 (19)0.0304 (17)0.0024 (15)0.0016 (14)0.0011 (15)
C140.040 (2)0.047 (2)0.043 (2)0.0103 (18)0.0029 (17)0.0117 (18)
C150.031 (2)0.061 (3)0.053 (2)0.0103 (19)0.0037 (18)0.010 (2)
C160.0298 (19)0.050 (2)0.044 (2)0.0019 (17)0.0021 (16)0.0055 (18)
C170.038 (2)0.037 (2)0.0304 (17)0.0025 (16)0.0024 (15)0.0036 (16)
C210.0290 (17)0.0362 (19)0.0269 (16)0.0007 (14)0.0031 (14)0.0020 (14)
C220.0300 (18)0.0319 (19)0.0339 (18)0.0017 (14)0.0038 (14)0.0033 (15)
C230.0350 (19)0.0335 (19)0.0313 (18)0.0014 (15)0.0064 (15)0.0009 (15)
C240.038 (2)0.047 (2)0.040 (2)0.0068 (17)0.0105 (17)0.0086 (18)
C250.0277 (19)0.067 (3)0.047 (2)0.0111 (18)0.0078 (17)0.007 (2)
C260.0302 (19)0.055 (2)0.0338 (19)0.0005 (17)0.0011 (15)0.0061 (17)
C270.038 (2)0.037 (2)0.0354 (19)0.0022 (16)0.0053 (16)0.0063 (16)
C310.0347 (19)0.035 (2)0.0387 (19)0.0021 (15)0.0036 (16)0.0005 (16)
C320.0318 (19)0.037 (2)0.0374 (19)0.0057 (15)0.0059 (15)0.0042 (16)
C330.037 (2)0.034 (2)0.0361 (19)0.0045 (16)0.0060 (15)0.0031 (15)
C340.042 (2)0.046 (2)0.046 (2)0.0124 (18)0.0102 (18)0.0020 (18)
C350.029 (2)0.063 (3)0.060 (3)0.0074 (19)0.0067 (19)0.004 (2)
C360.034 (2)0.051 (2)0.048 (2)0.0041 (17)0.0012 (17)0.0028 (19)
C370.045 (2)0.035 (2)0.041 (2)0.0069 (17)0.0068 (17)0.0002 (17)
Geometric parameters (Å, º) top
I11—As12.5911 (4)C14—C151.378 (5)
I12—As12.5939 (4)C14—H140.9300
I21—As22.5934 (4)C15—C161.387 (5)
I22—As22.5960 (4)C15—H150.9300
I31—As32.5938 (5)C16—H160.9300
I32—As32.6058 (5)C21—C221.383 (5)
As1—C111.977 (3)C21—C261.393 (5)
As2—C211.972 (3)C22—C231.396 (5)
As3—C311.978 (4)C22—H220.9300
O11—C171.277 (4)C23—C241.388 (5)
O11—H110.8200C23—C271.480 (5)
O12—C171.255 (4)C24—C251.373 (5)
O12—H11A0.8200C24—H240.9300
O21—C271.271 (4)C25—C261.379 (5)
O21—H210.8200C25—H250.9300
O22—C271.257 (4)C26—H260.9300
O22—H21A0.8200C31—C361.386 (5)
O31—C371.275 (4)C31—C321.389 (5)
O31—H310.8200C32—C331.397 (5)
O32—C371.262 (4)C32—H320.9300
O32—H31A0.8200C33—C341.400 (5)
C11—C161.385 (5)C33—C371.479 (5)
C11—C121.386 (5)C34—C351.372 (6)
C12—C131.391 (5)C34—H340.9300
C12—H120.9300C35—C361.381 (6)
C13—C141.394 (5)C35—H350.9300
C13—C171.475 (5)C36—H360.9300
C11—As1—I1199.57 (10)C21—C22—C23120.0 (3)
C11—As1—I1297.57 (10)C21—C22—H22120.0
I11—As1—I12102.621 (15)C23—C22—H22120.0
C21—As2—I2199.54 (10)C24—C23—C22119.8 (3)
C21—As2—I2296.84 (10)C24—C23—C27120.1 (3)
I21—As2—I22100.703 (15)C22—C23—C27120.2 (3)
C31—As3—I31101.06 (11)C25—C24—C23120.2 (3)
C31—As3—I3298.48 (11)C25—C24—H24119.9
I31—As3—I32102.632 (15)C23—C24—H24119.9
C17—O11—H11109.5C24—C25—C26120.0 (3)
C17—O12—H11A109.5C24—C25—H25120.0
C27—O21—H21109.5C26—C25—H25120.0
C27—O22—H21A109.5C25—C26—C21120.7 (3)
C37—O31—H31109.5C25—C26—H26119.7
C37—O32—H31A109.5C21—C26—H26119.7
C16—C11—C12119.8 (3)O22—C27—O21123.5 (3)
C16—C11—As1118.7 (3)O22—C27—C23118.4 (3)
C12—C11—As1120.6 (3)O21—C27—C23118.1 (3)
C11—C12—C13119.6 (3)C36—C31—C32119.9 (3)
C11—C12—H12120.2C36—C31—As3116.7 (3)
C13—C12—H12120.2C32—C31—As3122.6 (3)
C12—C13—C14120.6 (3)C31—C32—C33119.6 (3)
C12—C13—C17120.0 (3)C31—C32—H32120.2
C14—C13—C17119.5 (3)C33—C32—H32120.2
C15—C14—C13119.3 (3)C32—C33—C34119.7 (3)
C15—C14—H14120.4C32—C33—C37121.1 (3)
C13—C14—H14120.4C34—C33—C37119.2 (3)
C14—C15—C16120.4 (4)C35—C34—C33120.1 (4)
C14—C15—H15119.8C35—C34—H34120.0
C16—C15—H15119.8C33—C34—H34120.0
C11—C16—C15120.4 (4)C34—C35—C36120.3 (4)
C11—C16—H16119.8C34—C35—H35119.9
C15—C16—H16119.8C36—C35—H35119.9
O12—C17—O11123.1 (3)C35—C36—C31120.5 (4)
O12—C17—C13119.3 (3)C35—C36—H36119.7
O11—C17—C13117.6 (3)C31—C36—H36119.7
C22—C21—C26119.3 (3)O32—C37—O31122.9 (4)
C22—C21—As2121.6 (2)O32—C37—C33118.8 (3)
C26—C21—As2118.6 (3)O31—C37—C33118.3 (3)
I11—As1—C11—C16152.1 (3)C27—C23—C24—C25179.2 (4)
I12—As1—C11—C1647.9 (3)C23—C24—C25—C260.8 (6)
I11—As1—C11—C1238.7 (3)C24—C25—C26—C211.2 (6)
I12—As1—C11—C12142.9 (3)C22—C21—C26—C250.8 (6)
C16—C11—C12—C131.1 (5)As2—C21—C26—C25172.5 (3)
As1—C11—C12—C13168.0 (3)C24—C23—C27—O226.3 (5)
C11—C12—C13—C140.2 (5)C22—C23—C27—O22174.4 (3)
C11—C12—C13—C17179.4 (3)C24—C23—C27—O21174.2 (4)
C12—C13—C14—C150.8 (6)C22—C23—C27—O215.1 (5)
C17—C13—C14—C15180.0 (4)I31—As3—C31—C36154.1 (3)
C13—C14—C15—C160.2 (6)I32—As3—C31—C3649.3 (3)
C12—C11—C16—C151.8 (6)I31—As3—C31—C3236.3 (3)
As1—C11—C16—C15167.5 (3)I32—As3—C31—C32141.1 (3)
C14—C15—C16—C111.1 (6)C36—C31—C32—C330.6 (5)
C12—C13—C17—O12168.3 (3)As3—C31—C32—C33168.6 (3)
C14—C13—C17—O1210.9 (5)C31—C32—C33—C340.5 (5)
C12—C13—C17—O1111.9 (5)C31—C32—C33—C37179.7 (3)
C14—C13—C17—O11168.9 (3)C32—C33—C34—C350.3 (6)
I21—As2—C21—C2238.0 (3)C37—C33—C34—C35179.5 (4)
I22—As2—C21—C22140.1 (3)C33—C34—C35—C361.0 (6)
I21—As2—C21—C26150.5 (3)C34—C35—C36—C310.9 (6)
I22—As2—C21—C2648.3 (3)C32—C31—C36—C350.0 (6)
C26—C21—C22—C230.1 (5)As3—C31—C36—C35170.0 (3)
As2—C21—C22—C23171.6 (3)C32—C33—C37—O32175.9 (3)
C21—C22—C23—C240.2 (5)C34—C33—C37—O324.3 (5)
C21—C22—C23—C27179.5 (3)C32—C33—C37—O314.0 (5)
C22—C23—C24—C250.1 (6)C34—C33—C37—O31175.8 (4)

Experimental details

(I)(II)
Crystal data
Chemical formula[As(C7H5O2)I2][As(C7H5O2)I2]
Mr449.83449.83
Crystal system, space groupTriclinic, P1Monoclinic, P21/n
Temperature (K)296296
a, b, c (Å)4.8992 (2), 8.4434 (5), 13.6616 (9)7.6751 (5), 18.6142 (12), 22.0692 (12)
α, β, γ (°)107.148 (2), 91.569 (2), 96.376 (2)90, 90.206 (2), 90
V3)535.59 (5)3152.9 (3)
Z212
Radiation typeMo KαMo Kα
µ (mm1)8.909.07
Crystal size (mm)0.35 × 0.20 × 0.180.18 × 0.15 × 0.06
Data collection
DiffractometerBruker Nonius X8 APEXII CCD area-detector
diffractometer
Bruker Nonius X8 APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2004)
Multi-scan
(SADABS; Bruker, 2004)
Tmin, Tmax0.147, 0.2970.292, 0.612
No. of measured, independent and
observed [I > 2σ(I)] reflections
3909, 2144, 1859 23397, 5996, 5277
Rint0.0270.033
(sin θ/λ)max1)0.6250.610
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.109, 1.07 0.021, 0.046, 1.04
No. of reflections21445996
No. of parameters110325
H-atom treatmentH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.87, 1.670.88, 0.78

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXTL (Sheldrick, 2008), DIAMOND (Bergerhoff et al., 1996).

 

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