2,4-Diiodo-6-[(propyl­imino)­meth­yl]phenol

Liu, P.-G.; Wang, X.-N.; Yang, Y.-A.; Zhu, H.-L.

doi:10.1107/S1600536812005727

organic compounds

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doi:10.1107/S1600536812005727

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2,4-Diiodo-6-[(propylimino)methyl]phenol

Peng-Gang Liu,^a Xiao-Ning Wang,^a Yong-An Yang ^a and Hai-Liang Zhu ^a ^*

^aState Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing 210093, People's Republic of China
^*Correspondence e-mail: hailiang_zhu@163.com

(Received 7 February 2012; accepted 9 February 2012; online 24 February 2012)

The title compound, C₁₀H₁₁I₂NO, was prepared by the reaction of 3,5-diiodosalicylaldehyde with propylamine in ethanol. The molecule adopts an E conformation with respect to the C=N bond and the aromatic ring. The aromatic ring and the imino unit are close to being coplanar, with a dihedral angle of 2.6 (3)° between their planes. This planarity is assisted by the formation of an intramolecular O—H⋯O hydrogen bond.

Related literature

For the biological activity of Schiff base compounds, see: Chohan et al. (2012 ); Yan et al. (2011 ); Zhang et al. (2011 ). For their use as ligands in coordination chemistry, see: You et al. (2008 ); Xu et al. (2009 ); Chen et al. (2010 ); Cui et al. (2011 ). For standard bond distances, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₀H₁₁I₂NO
M_r = 415.00
Orthorhombic, P b c a
a = 10.7019 (14) Å
b = 7.1483 (9) Å
c = 32.404 (4) Å
V = 2478.9 (5) Å³
Z = 8
Mo Kα radiation
μ = 5.05 mm⁻¹
T = 298 K
0.21 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.417, T_max = 0.432
18976 measured reflections
2704 independent reflections
2224 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.104
S = 1.23
2704 reflections
131 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.96 e Å⁻³
Δρ_min = −0.89 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.90 (1)	1.82 (5)	2.567 (6)	138 (7)

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812005727/sj5194sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812005727/sj5194Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812005727/sj5194Isup3.cml

checkCIF report

Comment top

Schiff bases have been extensively studied because of their biological activity (Chohan et al., 2012; Yan et al., 2011; Zhang et al., 2011). In addition, Schiff bases have been shown to be versatile ligands for the preparation of coordination complexes (You et al., 2008; Xu et al., 2009; Chen et al., 2010; Cui et al., 2011). In the present paper, the structure of the new title Schiff base compound is reported.

The molecule of the compound exists in a trans of E configuration with respect to the methylidene unit. The torsion angles C1—C7—N1—C8, C7—N1—C8—C9, and N1—C8—C9—C10 are 0.9 (2), 60.5 (2), and 4.6 (2)°, respectively. Bond distances are within normal values (Allen et al., 1987). An intramolecular O1—H1···N1 hydrogen bond stabilises the molecular structure.

Related literature top

For the biological activity of Schiff base compounds, see: Chohan et al. (2012); Yan et al. (2011); Zhang et al. (2011). For their use as ligands in coordination chemistry, see: You et al. (2008); Xu et al. (2009); Chen et al. (2010); Cui et al. (2011). For standard bond distances, see: Allen et al. (1987).

Experimental top

3,5-Diiodosalicylaldehyde (0.37 g, 1 mmol) and propylamine (0.06 g, 1 mmol) were mixed in ethanol (20 ml). The mixture was stirred at room temperature for 30 min to give a yellow solution. Yellow block-shaped single crystals were obtained by slow evaporation of this solution in air.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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

Fig. 1. The molecular structure of the title compound, showing the atom labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. An intramolecular hydrogen bond is indicated by a dashed line.

2,4-Diiodo-6-[(propylimino)methyl]phenol top

Crystal data top

C₁₀H₁₁I₂NO	F(000) = 1536
M_r = 415.00	D_x = 2.224 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1027 reflections
a = 10.7019 (14) Å	θ = 2.3–24.5°
b = 7.1483 (9) Å	µ = 5.05 mm⁻¹
c = 32.404 (4) Å	T = 298 K
V = 2478.9 (5) Å³	Block, yellow
Z = 8	0.21 × 0.20 × 0.20 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2704 independent reflections
Radiation source: fine-focus sealed tube	2224 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ω scans	θ_max = 27.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
T_min = 0.417, T_max = 0.432	k = −9→8
18976 measured reflections	l = −41→41

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.23	w = 1/[σ²(F_o²) + (0.038P)² + 7.4143P] where P = (F_o² + 2F_c²)/3
2704 reflections	(Δ/σ)_max < 0.001
131 parameters	Δρ_max = 0.96 e Å⁻³
1 restraint	Δρ_min = −0.89 e Å⁻³

Crystal data top

C₁₀H₁₁I₂NO	V = 2478.9 (5) Å³
M_r = 415.00	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 10.7019 (14) Å	µ = 5.05 mm⁻¹
b = 7.1483 (9) Å	T = 298 K
c = 32.404 (4) Å	0.21 × 0.20 × 0.20 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2704 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2224 reflections with I > 2σ(I)
T_min = 0.417, T_max = 0.432	R_int = 0.030
18976 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	1 restraint
wR(F²) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.23	Δρ_max = 0.96 e Å⁻³
2704 reflections	Δρ_min = −0.89 e Å⁻³
131 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

	x	y	z	U_iso*/U_eq
I1	0.14060 (4)	0.18844 (7)	0.522554 (12)	0.05384 (15)
I2	−0.14147 (3)	0.44774 (7)	0.371421 (13)	0.05752 (16)
N1	0.3755 (4)	0.4405 (7)	0.34042 (16)	0.0449 (11)
O1	0.1359 (4)	0.4554 (7)	0.33939 (13)	0.0520 (10)
C1	0.2521 (5)	0.3571 (7)	0.39908 (16)	0.0378 (11)
C2	0.1382 (5)	0.3981 (8)	0.37824 (17)	0.0393 (11)
C3	0.0266 (5)	0.3772 (7)	0.40084 (16)	0.0396 (11)
C4	0.0250 (5)	0.3193 (8)	0.44167 (17)	0.0444 (12)
H4	−0.0501	0.3087	0.4559	0.053*
C5	0.1389 (5)	0.2770 (7)	0.46109 (17)	0.0397 (11)
C6	0.2501 (5)	0.2976 (7)	0.44023 (16)	0.0415 (11)
H6	0.3250	0.2716	0.4537	0.050*
C7	0.3699 (5)	0.3819 (8)	0.37775 (18)	0.0431 (12)
H7	0.4438	0.3544	0.3916	0.052*
C8	0.4981 (6)	0.4653 (9)	0.32071 (19)	0.0520 (14)
H8A	0.5636	0.4343	0.3402	0.062*
H8B	0.5085	0.5952	0.3127	0.062*
C9	0.5099 (6)	0.3412 (10)	0.28282 (19)	0.0572 (16)
H9A	0.4486	0.3791	0.2624	0.069*
H9B	0.4926	0.2126	0.2904	0.069*
C10	0.6403 (7)	0.3541 (14)	0.2642 (2)	0.077 (2)
H10A	0.6567	0.4809	0.2561	0.115*
H10B	0.6453	0.2740	0.2405	0.115*
H10C	0.7009	0.3154	0.2843	0.115*
H1	0.211 (3)	0.471 (11)	0.327 (2)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.0536 (2)	0.0651 (3)	0.0428 (2)	−0.0002 (2)	−0.00119 (15)	0.00945 (18)
I2	0.0393 (2)	0.0751 (3)	0.0582 (3)	0.00399 (19)	−0.01085 (16)	0.0073 (2)
N1	0.039 (2)	0.045 (3)	0.050 (3)	−0.002 (2)	0.0032 (19)	−0.001 (2)
O1	0.048 (2)	0.060 (3)	0.048 (2)	0.004 (2)	−0.0015 (17)	0.008 (2)
C1	0.037 (2)	0.032 (3)	0.045 (3)	0.003 (2)	−0.002 (2)	−0.005 (2)
C2	0.044 (3)	0.035 (3)	0.040 (3)	0.001 (2)	−0.004 (2)	−0.006 (2)
C3	0.039 (3)	0.035 (3)	0.045 (3)	0.004 (2)	−0.008 (2)	−0.002 (2)
C4	0.040 (3)	0.042 (3)	0.052 (3)	0.002 (2)	0.002 (2)	−0.002 (2)
C5	0.045 (3)	0.033 (3)	0.042 (3)	0.002 (2)	−0.003 (2)	0.001 (2)
C6	0.040 (3)	0.036 (3)	0.048 (3)	0.004 (2)	−0.005 (2)	−0.003 (2)
C7	0.041 (3)	0.043 (3)	0.045 (3)	0.002 (2)	−0.002 (2)	−0.009 (2)
C8	0.041 (3)	0.059 (4)	0.057 (3)	−0.006 (3)	0.005 (2)	0.000 (3)
C9	0.057 (4)	0.067 (4)	0.048 (3)	−0.006 (3)	0.005 (3)	−0.001 (3)
C10	0.070 (5)	0.099 (6)	0.061 (4)	−0.003 (4)	0.017 (3)	0.005 (4)

Geometric parameters (Å, º) top

I1—C5	2.090 (5)	C5—C6	1.377 (7)
I2—C3	2.097 (5)	C6—H6	0.9300
N1—C7	1.282 (8)	C7—H7	0.9300
N1—C8	1.471 (7)	C8—C9	1.520 (9)
O1—C2	1.324 (7)	C8—H8A	0.9700
O1—H1	0.900 (10)	C8—H8B	0.9700
C1—C6	1.400 (7)	C9—C10	1.523 (9)
C1—C2	1.424 (7)	C9—H9A	0.9700
C1—C7	1.449 (7)	C9—H9B	0.9700
C2—C3	1.409 (7)	C10—H10A	0.9600
C3—C4	1.386 (8)	C10—H10B	0.9600
C4—C5	1.405 (7)	C10—H10C	0.9600
C4—H4	0.9300

C7—N1—C8	119.4 (5)	N1—C7—H7	119.0
C2—O1—H1	116 (5)	C1—C7—H7	119.0
C6—C1—C2	120.1 (5)	N1—C8—C9	110.7 (5)
C6—C1—C7	120.3 (5)	N1—C8—H8A	109.5
C2—C1—C7	119.6 (5)	C9—C8—H8A	109.5
O1—C2—C3	120.7 (5)	N1—C8—H8B	109.5
O1—C2—C1	122.1 (5)	C9—C8—H8B	109.5
C3—C2—C1	117.2 (5)	H8A—C8—H8B	108.1
C4—C3—C2	122.6 (5)	C8—C9—C10	111.1 (6)
C4—C3—I2	119.7 (4)	C8—C9—H9A	109.4
C2—C3—I2	117.7 (4)	C10—C9—H9A	109.4
C3—C4—C5	118.7 (5)	C8—C9—H9B	109.4
C3—C4—H4	120.6	C10—C9—H9B	109.4
C5—C4—H4	120.6	H9A—C9—H9B	108.0
C6—C5—C4	120.5 (5)	C9—C10—H10A	109.5
C6—C5—I1	119.5 (4)	C9—C10—H10B	109.5
C4—C5—I1	120.0 (4)	H10A—C10—H10B	109.5
C5—C6—C1	120.9 (5)	C9—C10—H10C	109.5
C5—C6—H6	119.6	H10A—C10—H10C	109.5
C1—C6—H6	119.6	H10B—C10—H10C	109.5
N1—C7—C1	122.1 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.90 (1)	1.82 (5)	2.567 (6)	138 (7)

Experimental details

Crystal data
Chemical formula	C₁₀H₁₁I₂NO
M_r	415.00
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	298
a, b, c (Å)	10.7019 (14), 7.1483 (9), 32.404 (4)
V (Å³)	2478.9 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	5.05
Crystal size (mm)	0.21 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.417, 0.432
No. of measured, independent and observed [I > 2σ(I)] reflections	18976, 2704, 2224
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.104, 1.23
No. of reflections	2704
No. of parameters	131
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.96, −0.89

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.900 (10)	1.82 (5)	2.567 (6)	138 (7)

References

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o789

doi:10.1107/S1600536812005727

Open

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