(E)-4-Iodo-2-[(phenyl­imino)­meth­yl]phenol

Swetha, G.; Ida Malarselvi, R.; Ramachandra Raja, C.; Thiruvalluvar, A.; Priscilla, J.

doi:10.1107/S2414314619007880

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 4| Part 6| June 2019| x190788

https://doi.org/10.1107/S2414314619007880

Open

access

(E)-4-Iodo-2-[(phenylimino)methyl]phenol

G. Swetha,^a R. Ida Malarselvi,^b C. Ramachandra Raja,^a A. Thiruvalluvar ^c ^* and J. Priscilla ^d

^aPostgraduate and Research Department of Physics, Government Arts College (Autonomous), Kumbakonam 612 001, Tamilnadu, India, ^bPostgraduate and Research Department of Physics, D.G. Government Arts College for Women, Mayiladuthurai 609 001, Tamilnadu, India, ^cPrincipal, Kunthavai Naacchiyaar Government Arts College for Women (Autonomous), Thanjavur 613 007, Tamilnadu, India, and ^dPostgraduate Department of Physics, A.D.M. College for Women (Autonomous), Nagapattinam 611 001, Tamilnadu, India
^*Correspondence e-mail: thiruvalluvar.a@gmail.com

Edited by E. R. T. Tiekink, Sunway University, Malaysia (Received 31 May 2019; accepted 1 June 2019; online 4 June 2019)

The title compound, C₁₃H₁₀INO, is not planar as the dihedral angle between the planes of the two aryl rings is 44.5 (9)°. The configuration about the central C=N bond is E, and there is an intramolecular O—H⋯N hydrogen bond which generates an S(6) ring. The molecular packing is stabilized by weak C—H⋯π interactions. The structure was refined as a two-component inversion twin.

Keywords: crystal structure; salicylaldehyde derivative; O—H⋯N hydrogen bond; C—H⋯π interactions.

CCDC reference: 1920116

Structure description

We report here, as part of our on-going research (Ida Malarselvi et al., 2016 ; Swetha et al., 2017 , 2018 ), the synthesis and X-ray crystal structure determination of the title iodinated Schiff base compound, Fig. 1, which was synthesized from the condensation reaction of equimolar amounts of 5-iodosalicylaldehyde and aniline in DMSO.

Figure 1
A view of the molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level and showing the atom-numbering scheme. Dashed lines indicate the intramolecular hydrogen-bonding interaction (Table 1

The benzene and phenyl rings deviate from co-planarity with the dihedral angle between the two ring being 44.5 (9)°. The molecule has an E configuration about the C=N bond, and the C1—C7=N1—C8 torsion angle is 169.5 (17)°. There is a strong intra-molecular O1—H1⋯N1 hydrogen bond, Table 1, with an H⋯N separation of 1.94 Å which leads to an S(6) ring. The crystal structure (Fig. 2) is stabilized by three weak C—H⋯π interactions, see Table 1.

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 benzene ring and the C8–C13 phenyl ring, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.94	2.64 (2)	143
C5—H5⋯Cg1ⁱ	0.93	2.86	3.476 (15)	125
C9—H9⋯Cg2ⁱⁱ	0.93	2.81	3.48 (2)	129
C12—H12⋯Cg2ⁱⁱⁱ	0.93	2.82	3.55 (3)	136
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y, z-1]$ ; (ii) $[x+{\script{3\over 2}}, -y, z-1]$ ; (iii) $[x+{\script{1\over 2}}, -y, z]$ .

Figure 2
The molecular packing, viewed along the crystallographic c axis.

Yan et al. (2014 ) have reported the crystal structure determination of 4-bromo-2-[(phenylimino)methyl]phenol, in which the molecule is essentially planar (r.m.s. deviation = 0.026 Å), a result in contrast to our present study.

Synthesis and crystallization

5-Iodosalicylaldehyde (0.3 g) was dissolved in DMSO (15 ml). To this solution, aniline (0.2 g) was added dropwise with constant stirring for 1 h at 50°C. During this time, the solution turned light yellow. On standing for 1 month with slow evaporation of the solvent, light-orange crystals of the title compound suitable for the X-ray study were obtained.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The structure was refined as a two-component inversion twin.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₃H₁₀INO
M_r	323.12
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	296
a, b, c (Å)	7.0848 (8), 26.422 (3), 6.2664 (7)
V (Å³)	1173.1 (2)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	2.71
Crystal size (mm)	0.30 × 0.25 × 0.15

Data collection
Diffractometer	Bruker Kappa APEX3 CMOS
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.287, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	13051, 2057, 2043
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.080, 0.223, 1.18
No. of reflections	2057
No. of parameters	146
No. of restraints	148
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	2.90, −1.22
Absolute structure	Refined as an inversion twin.
Absolute structure parameter	0.53 (13)
Computer programs: APEX3, SAINT and XPREP (Bruker, 2016 ), SHELXT2018/2 (Sheldrick, 2015a ), SHELXL2018/3 (Sheldrick, 2015b ), DIAMOND (Brandenburg & Putz, 2018 ), PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 1920116

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314619007880/tk4058sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314619007880/tk4058Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314619007880/tk4058Isup3.cdx

Supporting information file. DOI: https://doi.org/10.1107/S2414314619007880/tk4058Isup4.cml

checkCIF report

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: APEX3 and SAINT (Bruker, 2016); data reduction: SAINT and XPREP (Bruker, 2016); program(s) used to solve structure: SHELXT2018/2 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2018); software used to prepare material for publication: SHELXL2018/3 (Sheldrick, 2015b), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

(E)-4-Iodo-2-[(phenylimino)methyl]phenol top

Crystal data top

C₁₃H₁₀INO	D_x = 1.830 Mg m⁻³
M_r = 323.12	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca2₁	Cell parameters from 9900 reflections
a = 7.0848 (8) Å	θ = 2.9–30.8°
b = 26.422 (3) Å	µ = 2.71 mm⁻¹
c = 6.2664 (7) Å	T = 296 K
V = 1173.1 (2) Å³	Plate, orange
Z = 4	0.30 × 0.25 × 0.15 mm
F(000) = 624

Data collection top

Bruker Kappa APEX3 CMOS diffractometer	2057 independent reflections
Radiation source: fine-focus sealed tube	2043 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.055
ω and φ scan	θ_max = 25.0°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −8→8
T_min = 0.287, T_max = 0.746	k = −31→31
13051 measured reflections	l = −7→7

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.080	w = 1/[σ²(F_o²) + (0.1256P)² + 10.5304P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.223	(Δ/σ)_max < 0.001
S = 1.18	Δρ_max = 2.90 e Å⁻³
2057 reflections	Δρ_min = −1.22 e Å⁻³
146 parameters	Absolute structure: Refined as an inversion twin.
148 restraints	Absolute structure parameter: 0.53 (13)

Special details top

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

Refinement. Refined as a two-component inversion twin. C-bound H atoms were placed in geometrically idealized positions with C—H = 0.93 Å. The OH H1 atom was placed geometrically with O—H = 0.82 Å.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.528 (2)	0.7086 (7)	0.466 (3)	0.036 (3)
C2	0.557 (2)	0.6640 (6)	0.586 (3)	0.031 (3)
H2	0.598694	0.666661	0.725680	0.038*
C3	0.526 (2)	0.6174 (6)	0.503 (2)	0.027 (3)
C4	0.461 (2)	0.6133 (7)	0.289 (3)	0.035 (4)
H4	0.439214	0.581274	0.232509	0.042*
C5	0.429 (2)	0.6565 (6)	0.1556 (19)	0.034 (4)
H5	0.388597	0.653661	0.015024	0.040*
C6	0.465 (2)	0.7045 (7)	0.255 (2)	0.035 (3)
C7	0.551 (2)	0.7588 (8)	0.554 (4)	0.044 (4)
H7	0.595451	0.760351	0.693338	0.053*
N1	0.5206 (18)	0.7982 (6)	0.470 (3)	0.038 (3)
O1	0.445 (2)	0.7439 (6)	0.126 (3)	0.063 (5)
H1	0.478128	0.769632	0.188944	0.095*
C8	0.516 (2)	0.8464 (8)	0.565 (3)	0.043 (4)
C9	0.582 (3)	0.8877 (6)	0.444 (4)	0.052 (5)
H9	0.627478	0.883081	0.305929	0.062*
C10	0.577 (4)	0.9366 (9)	0.538 (5)	0.069 (7)
H10	0.628761	0.964479	0.468623	0.083*
C11	0.491 (3)	0.9414 (7)	0.738 (4)	0.063 (6)
H11	0.482026	0.973329	0.799836	0.076*
C12	0.420 (4)	0.9000 (8)	0.847 (5)	0.077 (7)
H12	0.363078	0.904559	0.979138	0.092*
C13	0.431 (2)	0.8520 (7)	0.760 (3)	0.049 (5)
H13	0.382080	0.824147	0.831719	0.059*
I1	0.54634 (16)	0.55120 (4)	0.6950 (5)	0.0477 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.036 (8)	0.039 (6)	0.034 (7)	−0.001 (5)	−0.011 (6)	0.005 (5)
C2	0.033 (8)	0.034 (6)	0.028 (7)	−0.005 (5)	−0.009 (6)	0.000 (5)
C3	0.026 (7)	0.034 (6)	0.021 (6)	−0.007 (5)	−0.008 (5)	−0.001 (5)
C4	0.038 (9)	0.043 (8)	0.024 (6)	−0.004 (6)	−0.009 (6)	−0.001 (6)
C5	0.044 (8)	0.052 (7)	0.004 (8)	0.000 (6)	−0.005 (5)	−0.001 (5)
C6	0.027 (7)	0.045 (7)	0.032 (7)	0.002 (6)	−0.008 (5)	0.000 (5)
C7	0.038 (10)	0.047 (6)	0.047 (10)	−0.003 (6)	−0.010 (7)	−0.006 (5)
N1	0.019 (6)	0.051 (7)	0.044 (8)	−0.002 (6)	−0.008 (6)	−0.001 (6)
O1	0.074 (11)	0.034 (8)	0.082 (14)	0.002 (7)	−0.015 (8)	0.005 (7)
C8	0.019 (7)	0.054 (9)	0.056 (10)	0.004 (7)	−0.009 (7)	0.015 (7)
C9	0.043 (10)	0.039 (7)	0.074 (13)	0.008 (7)	0.028 (9)	−0.002 (7)
C10	0.045 (11)	0.052 (9)	0.111 (17)	0.002 (10)	0.009 (12)	−0.027 (10)
C11	0.044 (9)	0.039 (8)	0.106 (18)	0.008 (7)	0.003 (12)	−0.031 (9)
C12	0.052 (12)	0.058 (9)	0.120 (18)	0.009 (9)	0.009 (12)	−0.012 (10)
C13	0.020 (7)	0.052 (8)	0.074 (13)	−0.009 (7)	0.014 (7)	0.003 (7)
I1	0.0529 (8)	0.0357 (7)	0.0545 (8)	0.0010 (4)	−0.0052 (8)	0.0067 (8)

Geometric parameters (Å, º) top

C1—C6	1.402 (18)	N1—C8	1.41 (3)
C1—C2	1.412 (19)	O1—H1	0.8200
C1—C7	1.44 (3)	C8—C13	1.37 (2)
C2—C3	1.353 (19)	C8—C9	1.41 (2)
C2—H2	0.9300	C9—C10	1.42 (2)
C3—C4	1.421 (19)	C9—H9	0.9300
C3—I1	2.130 (16)	C10—C11	1.40 (2)
C4—C5	1.431 (19)	C10—H10	0.9300
C4—H4	0.9300	C11—C12	1.38 (2)
C5—C6	1.433 (19)	C11—H11	0.9300
C5—H5	0.9300	C12—C13	1.38 (2)
C6—O1	1.32 (2)	C12—H12	0.9300
C7—N1	1.19 (3)	C13—H13	0.9300
C7—H7	0.9300

C6—C1—C2	118.9 (17)	C7—N1—C8	127.6 (19)
C6—C1—C7	117.9 (17)	C6—O1—H1	109.5
C2—C1—C7	123.2 (16)	C13—C8—N1	119.1 (17)
C3—C2—C1	122.1 (15)	C13—C8—C9	123 (2)
C3—C2—H2	119.0	N1—C8—C9	117.5 (17)
C1—C2—H2	119.0	C8—C9—C10	118 (2)
C2—C3—C4	119.0 (15)	C8—C9—H9	120.9
C2—C3—I1	121.2 (11)	C10—C9—H9	120.9
C4—C3—I1	119.6 (12)	C11—C10—C9	118 (2)
C3—C4—C5	122.7 (15)	C11—C10—H10	121.1
C3—C4—H4	118.7	C9—C10—H10	121.1
C5—C4—H4	118.7	C12—C11—C10	122 (2)
C4—C5—C6	115.2 (13)	C12—C11—H11	119.1
C4—C5—H5	122.4	C10—C11—H11	119.1
C6—C5—H5	122.4	C13—C12—C11	121 (2)
O1—C6—C1	123.1 (17)	C13—C12—H12	119.7
O1—C6—C5	114.5 (14)	C11—C12—H12	119.7
C1—C6—C5	122.2 (16)	C8—C13—C12	118 (2)
N1—C7—C1	128 (2)	C8—C13—H13	120.8
N1—C7—H7	116.0	C12—C13—H13	120.8
C1—C7—H7	116.0

C6—C1—C2—C3	0 (3)	C6—C1—C7—N1	1 (3)
C7—C1—C2—C3	176.9 (17)	C2—C1—C7—N1	−175.8 (19)
C1—C2—C3—C4	0 (2)	C1—C7—N1—C8	169.5 (17)
C1—C2—C3—I1	−174.3 (13)	C7—N1—C8—C13	−42 (3)
C2—C3—C4—C5	0 (2)	C7—N1—C8—C9	145 (2)
I1—C3—C4—C5	174.8 (13)	C13—C8—C9—C10	7 (3)
C3—C4—C5—C6	−1 (2)	N1—C8—C9—C10	180 (2)
C2—C1—C6—O1	−175.6 (16)	C8—C9—C10—C11	−6 (4)
C7—C1—C6—O1	7 (3)	C9—C10—C11—C12	2 (4)
C2—C1—C6—C5	0 (3)	C10—C11—C12—C13	0 (4)
C7—C1—C6—C5	−177.3 (16)	N1—C8—C13—C12	−177 (2)
C4—C5—C6—O1	176.3 (16)	C9—C8—C13—C12	−4 (3)
C4—C5—C6—C1	1 (2)	C11—C12—C13—C8	1 (4)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 benzene ring and the C8–C13 phenyl ring, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.94	2.64 (2)	143
C5—H5···Cg1ⁱ	0.93	2.86	3.476 (15)	125
C9—H9···Cg2ⁱⁱ	0.93	2.81	3.48 (2)	129
C12—H12···Cg2ⁱⁱⁱ	0.93	2.82	3.55 (3)	136

Symmetry codes: (i) x+1/2, −y, z−1; (ii) x+3/2, −y, z−1; (iii) x+1/2, −y, z.

Acknowledgements

The authors are grateful to the Sophisticated Analytical Instrument Facility (SAIF), IITM, Chennai 600 036, Tamilnadu, India, for the single-crystal X-ray diffraction data.

References

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IUCrDATA

ISSN: 2414-3146

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(E)-4-Iodo-2-[(phenyl­imino)­meth­yl]phenol

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

organic compounds

(E)-4-Iodo-2-[(phenylimino)methyl]phenol