research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 6| June 2015| Pages 712-715

Crystal structure of 1-ethyl-5-iodo­indolin-2-one

aSchool of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China, bState Key Laboratory of Crystal Materials, Shandong University, Jinan 250100, People's Republic of China, and cBinzhou Key Laboratory of Material Chemistry, Department of Chemical Engineering, Binzhou University, Binzhou 256603, People's Republic of China
*Correspondence e-mail: fangqi@sdu.edu.cn

Edited by M. Gdaniec, Adam Mickiewicz University, Poland (Received 7 April 2015; accepted 22 May 2015; online 28 May 2015)

In the title indolinone derivative, C10H10INO, all the non-H atoms, except the terminal methyl C atom, are almost coplanar. The mol­ecules are arranged into columns extending along the a-axis direction and inter­act with the mol­ecules in adjacent columns via C—H⋯O hydrogen bonds [H⋯O distance = 2.57 (3) Å] and I⋯I short contacts of 3.8986 (3) Å. A one-dimensional zigzag iodine chain along the a axis is apparent between two neighbouring columns.

1. Chemical context

Indolinone derivatives play an important role in the pharma­ceutical industry and some of them show anti­neoplastic (Cane et al., 2000[Cane, A., Tournaire, M.-C., Barritault, D. & Crumeyrolle-Arias, M. (2000). Biochem. Biophys. Res. Commun. 276, 379-384.]), anti­bacterial (Kumar et al., 2013[Kumar, P. K. P., Priyadarshini, C. V., Arulmozhi, S. & Krishna Moorthy, P. (2013). Int. J. Clin. Pharm-Net. 5, 5240-5256.]) and anti-inflammatory (Mammone et al., 2006[Mammone, T., Åkesson, C., Gan, D., Giampapa, V. & Pero, W. R. (2006). Phytother. Res. 20, 178-183.]) activities. The indolinone skeleton can be also found in many known bioactive drugs, such as horsfiline (Murphy et al., 2005[Murphy, J. A., Tripoli, R., Khan, T. A. & Mali, U. W. (2005). Org. Lett. 7, 3287-3289.]), rhynchophylline (Deiters et al., 2006[Deiters, A., Pettersson, M. & Martin, S. F. (2006). J. Org. Chem. 71, 6547-6561.]) and the gelsemium alkaloids (Kitajima et al., 2006[Kitajima, M., Nakamura, T., Kogure, N., Ogawa, M., Mitsuno, Y., Ono, K., Yano, S., Aimi, N. & Takayama, H. (2006). J. Nat. Prod. 69, 715-718.]). In addition, indolinone derivatives are widely used in the spice industry and agriculture, as functional materials (Ji et al., 2010[Ji, L., Fang, Q., Yuan, M. S., Liu, Z. Q., Shen, Y. X. & Chen, H. F. (2010). Org. Lett. 12, 5192-5195.]) and dye inter­mediates.

[Scheme 1]

In recent years, the synthesis and crystal structures of many indolinone derivatives have been reported including 6-chloro-5-(2-chloro­eth­yl)oxindole (Nadkarni & Hallissey, 2008[Nadkarni, D. V. & Hallissey, J. F.(2008). Org. Process Res. Dev. 12, 1142-1145.]). We have recently synthesized and reported the crystal structures of several indolin-2-one derivatives including 1-phenyl-indolin-2-one (Wang et al., 2015[Wang, L., Zhang, M., Jin, Y.-Y., Lu, Q. & Fang, Q. (2015). Acta Cryst. C71, 69-74.]). As a continuation of our work in this field, we report here the synthesis and crystal structure of the title compound, 1-ethyl-5-iodo­indolin-2-one.

2. Structural commentary

The title mol­ecule is shown in Fig. 1[link]. The non-H atoms of the indoline core are virtually coplanar [mean deviation is 0.011 (3) Å with a maximum deviation of 0.023 (3) Å for C1]. The atoms C9, O1 and I1 are essentially co-planar with the indoline core, with deviations of 0.019 (4) Å for C9, 0.070 (3) Å for O1, and 0.127 (1) Å for I1. The sum of valence angles around N1 is 360.0°, indicating an sp2 hybridization of this atom. The two C—N bonds in the five-membered ring have a partial double-bond character [N1 C1 1.370 (4) Å; N1 C8 1.400 (3) Å], indicating conjugation of the π-electrons of the NC=O group with the π-electrons of the benzene ring.

[Figure 1]
Figure 1
The mol­ecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.

3. Supra­molecular features

The crystal packing in the title compound is shown in Figs. 2[link] and 3[link]. The mol­ecules are face-to-face parallel-packed forming a column along the a axis with ππ inter­actions centroid–centroid distances = 4.130 (2) and 4.462 (2) Å]. Mol­ecules from neighbouring columns are connected by a C—H⋯O hydrogen bond (Table 1[link]) with the formation of a layer-type aggregate parallel to (001). There is an I⋯I contact shorter than the sum (3.96 Å) of the van der Waals radii [I⋯Ii 3.8986 (3) Å, C—I⋯Ii 173.3 (3)°; symmetry code: (i) x − [{\script{1\over 2}}], −y − [{\script{1\over 2}}], −z + 2] joining the columns of mol­ecules in adjacent layers and forming a kind of 1-D zigzag chain along the a-axis direction (see Fig. 3[link]). An important feature of the columns is that they are polar, i.e. all mol­ecular dipole moments in the same column point in the same direction.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C2—H2A⋯O1i 0.99 (3) 2.57 (4) 3.554 (4) 169 (3)
Symmetry code: (i) [-x+3, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].
[Figure 2]
Figure 2
The view of the structure along the a axis, showing the C—H⋯O hydrogen bond between columns and the I⋯I inter­actions between columns. [Symmetry codes: (i) −x + 3, y + [{1\over 2}], −z + [{3\over 2}]; (ii) −x + 3, y − [{1\over 2}], −z + [{3\over 2}]; (iii) x − [{1\over 2}], −y − [{1\over 2}], −z + 2.]
[Figure 3]
Figure 3
The view of the structure along the b axis, showing the one-dimensional columnar structure and the zigzag iodine chains along the a axis.

DFT/b3lyp/genecp calculations were carried out, which took the pseudopotential basis set LanL2DZ for the iodine atom and the 6–311g(d) basis set for the other atoms, to optimize the mol­ecular geometry and calculate the dipole moment using the GAUSSIAN03 program (Frisch et al., 2003[Frisch, M. J., et al. (2003). GAUSSIAN03. Gaussian Inc., Pittsburgh, PA, USA.]). The dipole moment of the title mol­ecule (1.707 D) is much smaller than that of its precursor mol­ecule, 1-ethyl-5-iodo­indolin-2,3-dione (5.432 D). This difference may partly explain the non-centrosymmetry of the title crystal (space group P212121) and the centrosymmetry of the crystal of the precursor (Wang et al.,2014[Wang, L., Shen, Y.-X., Dong, J.-T., Zhang, M. & Fang, Q. (2014). Acta Cryst. E70, o67.]). On the other hand, the non-centrosymmetry of the title crystal may be better explained by the I⋯I inter­molecular inter­actions, for there are no I⋯I short contacts in the above centrosymmetric precursor crystal.

4. Database survey

A search of the Cambridge Structural Database (WebCSD, Version 5.36; last update April 2015; Groom & Allen, 2014[Groom, C. R. & Allen, F. H. (2014). Angew. Chem. Int. Ed. 53, 662-671.]) for 5-iodo­indolin-2-one derivatives gave 15 hits. Of these 16 structures (with the title structure included), the number of non-centrosymmetric structures (9) is slightly greater than the number of centrosymmetric structures (7). In these 16 structures, there are four structures which exhibit I⋯I short inter­molecular contacts and all the four structures are non-centrosymmetric (three of them belong to the P212121 space group and the other one belongs to the P63 space group; Takahashi et al., 2014[Takahashi, M., Murata, Y., Yagishita, F., Sakamoto, M., Sengoku, T. & Yoda, H. (2014). Chem. Eur. J. 20, 11091-11100.]). Therefore, the I⋯I contacts seem to promote non-centrosymmetric packing in this kind of compound.

5. Synthesis and crystallization

The title compound was synthesized by reduction of the precursor with an 80% hydrazine hydrate (see reaction scheme) . 1-Ethyl-5-iodo­indolin-2,3-dione precursor (1.714 g, 5.69 mmol) and 80% NH2NH2·H2O (19.0 mL) were added into a 50 mL flask and the mixture was stirred under reflux. The reaction progress was tracked by TLC. After 4.5 h, the reaction mixture was cooled down and poured into 100 mL water with precipitation of yellow solid. Then the mixture was extracted with CH2Cl2, the organic phase was washed with water and dried with MgSO4. The solvent was removed under reduced pressure and the crude product was purified by silica gel column chromatography with CHCl3 as eluent. The title compound was obtained as a colorless solid (1.509 g, yield 92.3%). m.p. 403–404 K. Crystals suitable for X-ray diffraction were obtained by slow evaporation of a CHCl3 solution.

[Scheme 2]

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. H atoms bound to aromatic C atoms and methyl­ene C atoms were located in difference maps and freely refined, leading to C—H distances of 0.91 to 1.02 Å. The three H atoms bound to methyl C atoms could also be located in difference maps but they were placed at calculated positions and treated using a riding-model approximation with C—H = 0.96 Å and Uiso(H) = 1.5 Ueq(C).

Table 2
Experimental details

Crystal data
Chemical formula C10H10INO
Mr 287.09
Crystal system, space group Orthorhombic, P212121
Temperature (K) 295
a, b, c (Å) 4.4622 (1), 8.2664 (2), 27.4400 (5)
V3) 1012.16 (4)
Z 4
Radiation type Mo Kα
μ (mm−1) 3.12
Crystal size (mm) 0.42 × 0.32 × 0.16
 
Data collection
Diffractometer Bruker APEXII CCD
Absorption correction Multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.354, 0.635
No. of measured, independent and observed [I > 2σ(I)] reflections 12175, 2938, 2878
Rint 0.020
(sin θ/λ)max−1) 0.704
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.021, 0.050, 1.21
No. of reflections 2938
No. of parameters 148
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.47, −0.69
Absolute structure Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1183 Friedel pairs
Absolute structure parameter 0.02 (2)
Computer programs: APEX2 and SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS97, SHELXL97 and SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information


Chemical context top

Indolinone derivatives play an important role in pharmaceutical industry and some of them show anti­neoplastic (Cane et al., 2000), anti­bacterial (Kumar et al., 2013) and anti-inflammatory (Mammone et al., 2006) activities. The indolinone skeleton can be also found in many known bioactive drugs, such as horsfiline (Murphy et al., 2005), rhynchophylline (Deiters et al., 2006) and the gelsemium alkaloids (Kitajima et al., 2006). In addition, indolinone derivatives are widely used in the spice industry and agriculture, as functional materials (Ji et al., 2010) and dye inter­mediates.

In recent years, the synthesis and crystal structures of many indolinone derivatives have been reported including 6-chloro-5-(2-chloro­ethyl)­oxindole (Nadkarni & Hallissey, 2008). We have recently synthesized and reported the crystal structures of several indolin-2-one derivatives including 1-phenyl-indolin-2-one (Wang et al., 2015). As a continuation of our work in this field, we report here the synthesis and crystal structure of the title compound, 1-ethyl-5-iodo­indolin-2-one.

Structural commentary top

The title molecule is shown in Fig. 1. The non-H atoms of the indoline core are virtually coplanar [mean deviation is 0.011 (3) Å with a maximum deviation of 0.023 (3) Å for C1]. The substituents C9, O1 and I1 are essentially co-planar with the indoline core, with deviations of 0.019 (4) Å for C9, 0.070 (3) Å for O1, and 0.127 (1) Å for I1. The sum of valence angles around N1 is 360.0°, indicating an sp2 hybridization of this atom. The two C—N bonds in the five-membered ring have a partial double-bond character [N1 C1 1.370 (4) Å; N1C8 1.400 (3) Å) indicating conjugation of the π-electrons of the NC=O group with the π-electrons of the benzene ring.

Supra­molecular features top

The crystal packing in the title compound is shown in Figs. 2 and 3. The molecules are face-to-face parallel-packed forming a one-dimensional column along the a axis with ππ inter­actions centroid–centroid distances = 4.130 (2) and 4.462 (2) Å]. Molecules from neighbouring columns are connected by a C—H···O hydrogen bond (Table 1) with the formation of a layer-type aggregate parallel to (001). There is an I···I contact shorter than the sum of van der Waals radii [I···I 3.8986 (3) Å, C—I···I 173.3 (3) °] joining the columns of molecules in adjacent layers and forming a kind of 1-D zigzag chain along the a-axis direction (see Fig. 3). An important feature of the columns is that they are polar, i.e. all molecular dipole moments in the same column point in the same direction.

DFT/b3lyp/genecp calculations were carried out, which took the pseudopotential basis set LanL2DZ for the iodine atom and the 6–311g(d) basis set for the other atoms, to optimize the molecular geometry and calculate the dipole moment using the GAUSSIAN03 program (Frisch et al., 2003). The dipole moment of the title molecule (1.707 D) is much smaller than that of its precursor molecule, 1-ethyl-5-iodo­indolin-2,3-dione (5.432 D). This difference may partly explain the non-centrosymmetry of the title crystal (space group P212121) and the centrosymmetry of the crystal of the precursor (Wang et al.,2014). On the other hand, the non-centrosymmetry of the title crystal may be better explained by the I···I inter­molecular inter­actions, for there are no I···I short contacts in the above centrosymmetric precursor crystal.

Database survey top

A search of the Cambridge Structural Database (WebCSD, Version 5.36; last update April 2015; Groom & Allen, 2014) for 5-iodo­indolin-2-one derivatives gave 15 hits. Of these 16 structures (with the title structure included), the number of non-centrosymmetric structures (9) is slightly greater than the number of centrosymmetric structures (7). In these 16 structures, there are four structures which exhibit I···I short inter­molecular contacts and all the four structures are non-centrosymmetric (three of them belong to the P212121 space group and the other one belongs to the P63 space group (Takahashi et al., 2014). Therefore, the I···I contacts seem to promote non-centrosymmetric packing in this kind of compound.

Synthesis and crystallization top

The title compound was synthesized by reduction of the precursor with an 80% hydrazine hydrate (see reaction scheme ). 1-Ethyl-5-iodo­indolin-2,3-dione precursor (1.714 g, 5.69 mmol) and 80% NH2NH2·H2O (19.0 mL) were added into a 50 mL flask and the mixture was stirred under reflux. The reaction progress was tracked by TLC. After 4.5 h, the reaction mixture was cooled down and poured into 100 mL water with precipitation of yellow solid. Then the mixture was extracted with CH2Cl2, the organic phase was washed with water and dried with MgSO4. The solvent was removed under reduced pressure and the crude product was purified by silica gel column chromatography with CHCl3 as eluent. The title compound was obtained as a colorless solid (1.509 g, yield 92.3%). m.p. 403–404 K. Crystals suitable for X-ray diffraction were obtained by slowly evaporation of CHCl3 solution.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. H atoms bound to aromatic C atoms and methyl­ene C atoms were located in difference maps and freely refined, leading to C—H distances of 0.91 to 1.02 Å. The three H atoms bound to methyl C atoms could also be located in difference maps but they were placed at calculated positions and treated using a riding-model approximation with C—H = 0.96 Å and Uiso(H) = 1.5 Ueq(C).

Related literature top

For related literature, see: Cane et al. (2000); Deiters et al. (2006); Durgesh & James (2008); Frisch et al. (2003); Groom & Allen (2014); Ji et al. (2010); Murphy et al. (2005); Kitajima et al. (2006); Kumar et al. (2013); Mammone et al. (2006); Takahashi et al. (2014); Wang et al. (2014, 2015).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. The view of the structure along the a axis, showing the C—H···O hydrogen bond between columns and the I···I interactions between columns. [Symmetry codes: (i) -x + 3, y + 1/2, -z + 3/2; (ii) -x + 3, y - 1/2, -z + 3/2; (iii) x - 1/2, -y - 1/2, -z + 2.]
[Figure 3] Fig. 3. The view of the structure along the b axis, showing the one-dimensional columnar structure and the zigzag iodine chains along the a axis.
1-Ethyl-5-iodoindolin-2-one top
Crystal data top
C10H10INODx = 1.884 Mg m3
Mr = 287.09Melting point = 403–404 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 9948 reflections
a = 4.4622 (1) Åθ = 2.5–30.0°
b = 8.2664 (2) ŵ = 3.12 mm1
c = 27.4400 (5) ÅT = 295 K
V = 1012.16 (4) Å3Parallelepiped, orange
Z = 40.42 × 0.32 × 0.16 mm
F(000) = 552
Data collection top
Bruker APEXII CCD
diffractometer
2938 independent reflections
Radiation source: fine-focus sealed tube2878 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
Detector resolution: 8.3 pixels mm-1θmax = 30.0°, θmin = 2.6°
ω scansh = 66
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 119
Tmin = 0.354, Tmax = 0.635l = 3733
12175 measured reflections
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.021 w = 1/[σ2(Fo2) + (0.0144P)2 + 0.4592P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.050(Δ/σ)max = 0.002
S = 1.21Δρmax = 0.47 e Å3
2938 reflectionsΔρmin = 0.69 e Å3
148 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0014 (3)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 1183 Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.02 (2)
Crystal data top
C10H10INOV = 1012.16 (4) Å3
Mr = 287.09Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 4.4622 (1) ŵ = 3.12 mm1
b = 8.2664 (2) ÅT = 295 K
c = 27.4400 (5) Å0.42 × 0.32 × 0.16 mm
Data collection top
Bruker APEXII CCD
diffractometer
2938 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
2878 reflections with I > 2σ(I)
Tmin = 0.354, Tmax = 0.635Rint = 0.020
12175 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.021H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.050Δρmax = 0.47 e Å3
S = 1.21Δρmin = 0.69 e Å3
2938 reflectionsAbsolute structure: Flack (1983), 1183 Friedel pairs
148 parametersAbsolute structure parameter: 0.02 (2)
0 restraints
Special details top

Experimental. Scan width 0.4° ω, Crystal to detector distance 6.20 cm, exposure time 20 s, 17 h for data collection

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
I10.57349 (4)0.10015 (2)0.963176 (7)0.05126 (7)
C50.7961 (6)0.0703 (3)0.91955 (9)0.0404 (5)
O11.3877 (6)0.3521 (3)0.74792 (8)0.0644 (7)
C40.8354 (6)0.0383 (3)0.87003 (10)0.0410 (5)
C30.9948 (5)0.1476 (3)0.84294 (9)0.0386 (6)
C81.1096 (6)0.2881 (3)0.86420 (9)0.0394 (5)
N11.2652 (5)0.3781 (3)0.82916 (8)0.0429 (5)
C91.4198 (8)0.5309 (4)0.83826 (12)0.0505 (6)
C101.2102 (8)0.6717 (4)0.84543 (12)0.0539 (7)
H10A1.07720.67950.81800.081*
H10B1.32420.76980.84820.081*
H10C1.09550.65570.87460.081*
C11.2634 (7)0.3027 (3)0.78470 (10)0.0472 (6)
C21.0825 (9)0.1476 (3)0.78985 (10)0.0488 (6)
C71.0700 (8)0.3218 (3)0.91288 (10)0.0456 (5)
C60.9096 (8)0.2096 (4)0.94064 (9)0.0472 (6)
H2A1.216 (8)0.054 (4)0.7827 (11)0.053 (9)*
H2B0.899 (12)0.165 (5)0.7685 (17)0.103 (16)*
H40.754 (8)0.062 (4)0.8534 (12)0.058 (9)*
H60.884 (8)0.234 (4)0.9737 (11)0.051 (9)*
H71.143 (7)0.419 (4)0.9266 (11)0.053 (9)*
H9A1.548 (9)0.555 (4)0.8089 (13)0.067 (11)*
H9B1.528 (10)0.520 (5)0.8662 (14)0.075 (12)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.05236 (10)0.05416 (11)0.04726 (10)0.00328 (9)0.00305 (9)0.01516 (8)
C50.0395 (12)0.0407 (14)0.0410 (12)0.0021 (10)0.0017 (10)0.0086 (10)
O10.0785 (16)0.0576 (13)0.0570 (13)0.0032 (13)0.0277 (13)0.0062 (10)
C40.0445 (13)0.0333 (12)0.0451 (13)0.0004 (9)0.0016 (10)0.0007 (10)
C30.0434 (14)0.0350 (12)0.0374 (12)0.0044 (8)0.0043 (9)0.0006 (9)
C80.0386 (12)0.0356 (11)0.0440 (12)0.0026 (10)0.0029 (10)0.0009 (10)
N10.0479 (11)0.0335 (11)0.0473 (11)0.0035 (10)0.0100 (10)0.0003 (9)
C90.0432 (13)0.0488 (15)0.0596 (17)0.0113 (14)0.0002 (15)0.0038 (12)
C100.0615 (18)0.0403 (15)0.0598 (17)0.0119 (14)0.0008 (15)0.0031 (13)
C10.0537 (16)0.0393 (13)0.0486 (15)0.0047 (13)0.0125 (13)0.0039 (12)
C20.0664 (17)0.0389 (13)0.0412 (13)0.0003 (15)0.0159 (15)0.0040 (10)
C70.0526 (14)0.0414 (13)0.0428 (13)0.0052 (14)0.0023 (13)0.0048 (10)
C60.0530 (14)0.0538 (15)0.0349 (12)0.0018 (15)0.0015 (13)0.0009 (11)
Geometric parameters (Å, º) top
I1—C52.099 (3)C9—C101.506 (5)
C5—C61.384 (4)C9—H9A1.01 (4)
C5—C41.395 (4)C9—H9B0.91 (4)
O1—C11.222 (3)C10—H10A0.9600
C4—C31.369 (4)C10—H10B0.9600
C4—H41.02 (3)C10—H10C0.9600
C3—C81.397 (4)C1—C21.521 (4)
C3—C21.508 (4)C2—H2A0.99 (3)
C8—C71.376 (4)C2—H2B1.02 (5)
C8—N11.400 (3)C7—C61.398 (4)
N1—C11.370 (4)C7—H70.95 (3)
N1—C91.461 (4)C6—H60.94 (3)
C6—C5—C4121.3 (2)C9—C10—H10A109.5
C6—C5—I1119.53 (19)C9—C10—H10B109.5
C4—C5—I1119.2 (2)H10A—C10—H10B109.5
C3—C4—C5118.0 (3)C9—C10—H10C109.5
C3—C4—H4118.8 (19)H10A—C10—H10C109.5
C5—C4—H4123.3 (19)H10B—C10—H10C109.5
C4—C3—C8120.8 (2)O1—C1—N1125.5 (3)
C4—C3—C2131.2 (3)O1—C1—C2126.8 (3)
C8—C3—C2108.0 (2)N1—C1—C2107.7 (2)
C7—C8—C3121.8 (3)C3—C2—C1103.1 (2)
C7—C8—N1128.5 (3)C3—C2—H2A110.2 (18)
C3—C8—N1109.7 (2)C1—C2—H2A108 (2)
C1—N1—C8111.5 (2)C3—C2—H2B110 (3)
C1—N1—C9123.3 (2)C1—C2—H2B105 (3)
C8—N1—C9125.2 (2)H2A—C2—H2B118 (3)
N1—C9—C10113.4 (3)C8—C7—C6117.4 (3)
N1—C9—H9A107 (2)C8—C7—H7121 (2)
C10—C9—H9A108 (2)C6—C7—H7121.6 (19)
N1—C9—H9B108 (3)C5—C6—C7120.8 (2)
C10—C9—H9B107 (3)C5—C6—H6122 (2)
H9A—C9—H9B113 (3)C7—C6—H6117 (2)
C6—C5—C4—C31.2 (4)C8—N1—C1—O1178.2 (3)
I1—C5—C4—C3176.70 (19)C9—N1—C1—O10.1 (5)
C5—C4—C3—C81.1 (4)C8—N1—C1—C21.3 (3)
C5—C4—C3—C2178.5 (3)C9—N1—C1—C2179.6 (3)
C4—C3—C8—C70.5 (4)C4—C3—C2—C1178.6 (3)
C2—C3—C8—C7179.1 (3)C8—C3—C2—C11.0 (3)
C4—C3—C8—N1179.4 (2)O1—C1—C2—C3178.1 (3)
C2—C3—C8—N10.3 (3)N1—C1—C2—C31.4 (3)
C7—C8—N1—C1178.0 (3)C3—C8—C7—C60.0 (4)
C3—C8—N1—C10.7 (3)N1—C8—C7—C6178.6 (3)
C7—C8—N1—C90.2 (5)C4—C5—C6—C70.7 (5)
C3—C8—N1—C9178.9 (3)I1—C5—C6—C7177.2 (2)
C1—N1—C9—C10108.7 (3)C8—C7—C6—C50.0 (5)
C8—N1—C9—C1073.2 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2A···O1i0.99 (3)2.57 (4)3.554 (4)169 (3)
Symmetry code: (i) x+3, y1/2, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2A···O1i0.99 (3)2.57 (4)3.554 (4)169 (3)
Symmetry code: (i) x+3, y1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC10H10INO
Mr287.09
Crystal system, space groupOrthorhombic, P212121
Temperature (K)295
a, b, c (Å)4.4622 (1), 8.2664 (2), 27.4400 (5)
V3)1012.16 (4)
Z4
Radiation typeMo Kα
µ (mm1)3.12
Crystal size (mm)0.42 × 0.32 × 0.16
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.354, 0.635
No. of measured, independent and
observed [I > 2σ(I)] reflections
12175, 2938, 2878
Rint0.020
(sin θ/λ)max1)0.704
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.021, 0.050, 1.21
No. of reflections2938
No. of parameters148
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.47, 0.69
Absolute structureFlack (1983), 1183 Friedel pairs
Absolute structure parameter0.02 (2)

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

This work was supported by the National Science Foundation of China (grant Nos. 21472116 and 20972089).

References

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Volume 71| Part 6| June 2015| Pages 712-715
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