Crystal structure and Hirshfeld surface analysis of (E)-2-{[(2-iodo­phen­yl)imino]­meth­yl}-6-methyl­phenol

Kansiz, S.; Agar, T.; Dege, N.; Dogan, O.E.; Ahmed, R.; Saif, E.

doi:10.1107/S2056989020011974

research communications

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 76| Part 10| October 2020| Pages 1595-1598

https://doi.org/10.1107/S2056989020011974

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Crystal structure and Hirshfeld surface analysis of (E)-2-{[(2-iodophenyl)imino]methyl}-6-methylphenol

Sevgi Kansiz,^a ^* Tuggan Agar,^b Necmi Dege,^c Onur Erman Dogan,^d Ruby Ahmed ^e and Eiad Saif ^f ^*

^aSamsun University, Faculty of Engineering, Department of Fundamental Sciences, 55420, Samsun, Turkey, ^bYeditepe University, Department of Chemical Engineering, 34755, İstanbul, Turkey, ^cOndokuz Mayıs University, Faculty of Arts and Sciences, Department of Physics, 55139, Samsun, Turkey, ^dOndokuz Mayıs University, Faculty of Arts and Sciences, Department of Chemistry, 55139, Samsun, Turkey, ^eDepartment of Applied Chemistry, ZHCET, Aligarh Muslim University, Aligarh, 202002, UP, India, and ^fDepartment of Computer and Electronic Engineering Technology, Sana'a Community, College, Sana'a, Yemen
^*Correspondence e-mail: sevgi.kansiz@samsun.edu.tr, eiad.saif@scc.edu.ye

Edited by M. Zeller, Purdue University, USA (Received 27 July 2020; accepted 31 August 2020; online 4 September 2020)

The title compound, C₁₄H₁₂INO, was synthesized by condensation of 2-hydroxy-3-methylbenzaldehyde and 2-iodoaniline, and crystallizes in the orthorhombic space group P2₁2₁2₁. The 2-iodophenyl and benzene rings are twisted with respect to each other, making a dihedral angle of 31.38 (2)°. The molecular structure is stabilized by an O—H⋯N hydrogen bond, forming an S(6) ring motif. In the crystal, molecules are linked by C—H⋯π interactions, resulting in the formation of sheets along the a-axis direction. Within the sheets, very weak π–π stacking interactions lead to additional stabilization. The Hirshfeld surface analysis and fingerprint plots reveal that the crystal structure is dominated by H⋯H (37.1%) and C⋯H (30.1%) contacts. Hydrogen bonding and van der Waals interactions are the dominant interactions in the crystal packing. The crystal studied was refined as a two-component inversion twin.

Keywords: crystal structure; 2-iodophenyl; Schiff base; Hirshfeld surface analysis.

CCDC reference: 2026445

1. Chemical context

Imines derived from o-hydroxy aromatic carbonyls are of interest because of their ability to form an asymmetric intramolecular hydrogen bond between the oxygen atom of the hydroxyl group and the nitrogen atom of the imine moiety (Dominiak et al., 2003 ). This ability has a decisive impact on the biological and thermo- or photochromic properties of o-hydroxy aromatic Schiff bases and makes them very useful compounds in chemistry, biochemistry, medicine, and technology (Vlad et al., 2018 ; Bouhidel et al., 2018 ; Faizi et al., 2020a ,b ). A very important issue is determining the positions of tautomeric equilibria in these compounds and various instrumental research techniques are used to provide insight into the structure of molecules of studied o-hydroxy Schiff bases (Wojciechowski et al., 2003 ; Faizi et al., 2020c ,d ).

In the present study, a new Schiff base, (E)-2-{[(2-iodophenyl)imino]methyl}-6-methylphenol, was obtained in crystalline form from the reaction of 2-hydroxy-3-methylbenzaldehyde with 2-iodoaniline. We report here the synthesis and the crystal and molecular structures of the title compound, along with the results of a Hirshfeld surface analysis.

2. Structural commentary

Depending on the tautomers, two types of intramolecular hydrogen bonds are observed in Schiff bases: O—H⋯N in enol–imine and N—H⋯O in keto–amine tautomers. Most of these compounds are non-planar. The title compound, (I), is a Schiff base derivative from 2-hydroxy-3-methylbenzaldehyde, which crystallizes in the phenol–imine tautomeric form with an E configurationfor the imine functionality. The asymmetric unit of (I) contains one molecule (Fig. 1). The molecule is non-planar with the 2-iodophenyl and benzene rings twisted with respect to each other at a dihedral angle of 31.38 (2)°. The hydroxyl H atom is involved in a strong intramolecular O—H⋯N hydrogen bond, forming an S(6) ring motif, which stabilizes the molecular structure and induces the Schiff base atoms (N1, C7) to be coplanar with the methylphenol moiety. Of this planar unit (r.m.s deviation = 0.0274 Å), atoms O1 and N1 show the largest deviations from planarity in positive and negative directions [O1 = 0.035 (4) Å and N1 = −0.060 (4) Å]. The C7—N1 and C13—O1 bonds of the title compound are the most important indicators of the tautomeric type. The C13—O1 bond is of double-bond character for the keto–amine tautomer, whereas this bond displays single-bond character in the enol–imine tautomer. In addition, the C7—N1 bond is also a double bond in the enol–imine tautomer and a single bond length in the keto–amine tautomer. In the title compound, the enol–imine form is favored over the keto-amine form, as indicated by the C13—O1 [1.352 (6) Å] and C7—N1 [1.286 (8) Å] bonds, whose lengths indicate a high degree of single-bond and double-bond character, respectively. The shortest C—C distance (C3—C4) is 1.344 (11) Å in the C1–C6 ring with the weighted average ring bond distance being 1.376 (11) Å for this ring.

Figure 1
The molecular structure of the title compound, with atom labelling. The intramolecular N—H⋯O hydrogen bond (Table 1

) is indicated by a dashed line. Displacement ellipsoids are drawn at the 40% probability level.

3. Supramolecular features

In the crystal structure, the molecules are connected into sheets extending along the a-axis direction by C2—H2⋯Cg2ⁱ interactions (Table 1; Fig. 2). Within the sheets, very weak π–π stacking interactions are observed with a centroid-to-centroid distance Cg1⋯Cg2ⁱⁱ of 4.093 (2) Å (Fig. 3), where Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively.

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C8–C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.93 (7)	1.82 (7)	2.634 (6)	144 (6)
C2—H2⋯Cg2ⁱ	0.93	2.97 (6)	3.7445 (4)	142 (4)
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 2
A view of the crystal packing of the title compound in a view parallel to the bc plane. C—H⋯π(ring) interactions are indicated by dashed lines.

Figure 3
A view of the crystal packing of the title compound along the a axis. π(Cg1)⋯π(Cg2) interactions are indicated by dashed lines.

4. Hirshfeld surface analysis

A Hirshfeld surface analysis (Spackman & Jayatilaka, 2009 ) was carried out using CrystalExplorer17.5 (Turner et al., 2017 ). The Hirshfeld surfaces and the associated two-dimensional fingerprint plots were used to quantify the various intermolecular interactions in the structure. The Hirshfeld surfaces (d_norm and shape-index) of the title compound are illustrated in Fig. 4. There are no prominent red spots on the surface, hence most of the interactions are weak non-covalent interactions. The diffuse white areas identified in Fig. 4a and red areas on phenyl rings mapped with shape-index (Fig. 4b) correspond to the H⋯π contacts resulting from hydrogen bond C—H⋯π(ring) (Table 1) and π–π stacking interactions. The major intermolecular interactions in the crystal structure are H⋯H, H⋯C and H⋯I interactions, which make individual contributions of 37.1%, 30.1% and 18%, respectively. The fingerprint plots are shown in Fig. 5. There are also O⋯H (6.4%), N⋯H (3.6%) and C⋯C (23.3%) contacts. The Hirshfeld surface analysis confirms the importance of H-atom contacts in establishing the packing. The large number of H⋯H and C⋯H interactions suggest that van der Waals interactions play the major role in the crystal packing.

Figure 4
The Hirshfeld surfaces of the title compound mapped over (a) d_norm and (b) shape-index.

Figure 5
Two-dimensional fingerprint plots for the title compound, with a d_norm view and the relative contribution of the atom pairs to the Hirshfeld surface.

5. Database survey

A search of the Cambridge Structural Database (CSD, version 5.41, update of November 2019; Groom et al., 2016 ) for the (E)-2-[(2-iodophenylimino)methyl]phenol gave six hits: bis[N-(2-iodophenyl)-2-oxynaphthaldiminato-N,O]copper(II) (HABFIA; Unver, 2002 ), bis(m-methanolato)bis(2-{[(5,7-diiodoquinolin-8-yl)imino]methyl}phenolato)bis(isothiocyanato)diiron(III) methanol solvate (HIDJOW; Sahadevan et al., 2018 ), bis(m-oxo)bis(m-methanolato)tetrakis(2-{[(5,7-diiodoquinolin-8-yl)imino]methyl}phenolato)bis(isothiocyanato)tetrairon(III) dichloromethane solvate (HIDJUC; Sahadevan et al., 2018), 2-{[(5,7-diiodoquinolin-8-yl)imino]methyl}phenol (HIDKAJ; Sahadevan et al., 2018), 2-iodo-salicylideneaniline (QQQANJ; Bernstein, 1967 ) and 2-[(2-iodophenyl)iminomethyl]phenol (RAVTIR; Elmali & Elerman, 1997 ). In HABFIA, the C—O bond length is 1.293 (3) Å, compared to 1.339 (5) Å for this bond in RAVTIR. Similar values are observed in the crystal of the title compound. The C—N bond lengths are 1.306 (3) and 1.267 (5) Å in HABFIA and RAVTIR, respectively. The molecules of HABFIA and RAVTIR have the same configuration as the title compound, while the other compounds listed above have different configurations.

6. Synthesis and crystallization

The title compound was prepared by refluxing mixed solutions of 2-hydroxy-3-methylbenzaldehyde (34.0 mg, 0.25 mmol) in ethanol (20 ml) and 2-iodoaniline (54.7 mg, 0.25 mmol) in ethanol (20 ml). The reaction mixture was stirred for 4 h under reflux. Single crystals of the title compound for X-ray analysis were obtained by slow evaporation of an ethanol solution (yield 72%, m.p. 410–412 K).

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The C-bound H atoms were placed according to the difference-Fourier map and refined using a riding model: C—H = 0.93–0.96 Å with U_iso(H) = 1.5U_eq(C-methyl) and 1.2U_eq(C) for other H atoms. Hydroxyl H atoms were placed according to a difference-Fourier map and were freely refined. The crystal studied was refined as a two-component inversion twin. This reflection file contains the non-overlapping reflections of the two twin components as well as the overlapping reflections. The BASF parameter for this two-component twin refined to −0.03242 (8).

Table 2
Experimental details

Crystal data
Chemical formula	C₁₄H₁₂INO
M_r	337.15
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	8.1730 (4), 11.8143 (9), 13.1721 (8)
V (Å³)	1271.88 (14)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	2.50
Crystal size (mm)	0.66 × 0.34 × 0.13

Data collection
Diffractometer	Stoe IPDS 2
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002 )
T_min, T_max	0.365, 0.784
No. of measured, independent and observed [I > 2σ(I)] reflections	5163, 2482, 1949
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.063, 0.92
No. of reflections	2482
No. of parameters	160
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.21
Computer programs: X-AREA and X-RED (Stoe & Cie, 2002), SHELXT2017/1 (Sheldrick, 2015a ), SHELXL2017/1 (Sheldrick, 2015b ), PLATON (Spek, 2020 ) and WinGX (Farrugia, 2012 ).

Supporting information

CCDC reference: 2026445

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989020011974/zl2795sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989020011974/zl2795Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989020011974/zl2795Isup3.cml

checkCIF report

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXT2017/1 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2017/1 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2020); software used to prepare material for publication: WinGX (Farrugia, 2012).

(E)-2-{[(2-Iodophenyl)imino]methyl}-6-methylphenol top

Crystal data top

C₁₄H₁₂INO	D_x = 1.761 Mg m⁻³
M_r = 337.15	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 6431 reflections
a = 8.1730 (4) Å	θ = 2.5–32.6°
b = 11.8143 (9) Å	µ = 2.50 mm⁻¹
c = 13.1721 (8) Å	T = 296 K
V = 1271.88 (14) Å³	Rod, orange
Z = 4	0.66 × 0.34 × 0.13 mm
F(000) = 656

Data collection top

Stoe IPDS 2 diffractometer	2482 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	1949 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.033
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.0°, θ_min = 2.9°
rotation method scans	h = −8→10
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −14→14
T_min = 0.365, T_max = 0.784	l = −12→16
5163 measured reflections

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)] = 0.031	Hydrogen site location: mixed
wR(F²) = 0.063	H atoms treated by a mixture of independent and constrained refinement
S = 0.92	w = 1/[σ²(F_o²) + (0.0304P)²] where P = (F_o² + 2F_c²)/3
2482 reflections	(Δ/σ)_max = 0.001
160 parameters	Δρ_max = 0.46 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

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.

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

	x	y	z	U_iso*/U_eq
C1	0.5327 (7)	0.7863 (4)	0.8238 (6)	0.0512 (13)
C2	0.6359 (10)	0.8192 (5)	0.9003 (6)	0.0664 (19)
H2	0.598522	0.866780	0.951494	0.080*
C3	0.7966 (11)	0.7810 (6)	0.9008 (6)	0.076 (2)
H3	0.867715	0.803861	0.951899	0.092*
C4	0.8492 (8)	0.7109 (5)	0.8273 (7)	0.0720 (18)
H4	0.956517	0.684703	0.828468	0.086*
C5	0.7452 (7)	0.6773 (5)	0.7497 (6)	0.0632 (17)
H5	0.783507	0.629118	0.699235	0.076*
C6	0.5849 (7)	0.7150 (5)	0.7469 (5)	0.0508 (14)
C7	0.5196 (7)	0.6589 (5)	0.5815 (5)	0.0523 (13)
H7	0.628176	0.672300	0.564200	0.063*
C8	0.4100 (7)	0.6148 (4)	0.5043 (5)	0.0475 (14)
C9	0.4719 (8)	0.5869 (5)	0.4092 (5)	0.0599 (17)
H9	0.582202	0.598902	0.395435	0.072*
C10	0.3738 (9)	0.5425 (5)	0.3361 (6)	0.0661 (17)
H10	0.416758	0.523217	0.273023	0.079*
C11	0.2093 (10)	0.5262 (5)	0.3564 (5)	0.0624 (17)
H11	0.142297	0.496373	0.305986	0.075*
C12	0.1420 (8)	0.5532 (5)	0.4495 (5)	0.0535 (15)
C13	0.2432 (7)	0.5988 (4)	0.5232 (5)	0.0486 (15)
C14	−0.0374 (8)	0.5358 (6)	0.4703 (7)	0.075 (2)
H14A	−0.050482	0.493780	0.532175	0.113*
H14B	−0.085832	0.494527	0.415201	0.113*
H14C	−0.090242	0.607994	0.476842	0.113*
I1	0.29233 (6)	0.84637 (4)	0.82323 (4)	0.07511 (17)
O1	0.1754 (5)	0.6247 (4)	0.6139 (4)	0.0648 (12)
N1	0.4728 (6)	0.6802 (3)	0.6727 (5)	0.0507 (11)
H1	0.254 (8)	0.660 (5)	0.654 (6)	0.08 (2)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.050 (3)	0.050 (3)	0.053 (3)	−0.005 (2)	0.002 (4)	0.002 (3)
C2	0.074 (5)	0.058 (4)	0.067 (5)	−0.010 (3)	−0.003 (4)	−0.005 (3)
C3	0.073 (5)	0.075 (4)	0.081 (5)	−0.014 (4)	−0.025 (5)	−0.001 (4)
C4	0.058 (4)	0.068 (3)	0.090 (5)	−0.005 (3)	−0.015 (5)	−0.004 (5)
C5	0.050 (4)	0.057 (4)	0.083 (5)	0.002 (3)	−0.002 (3)	−0.007 (3)
C6	0.049 (4)	0.047 (3)	0.057 (4)	−0.002 (3)	−0.007 (3)	0.001 (3)
C7	0.049 (3)	0.050 (3)	0.058 (4)	0.002 (3)	0.008 (3)	0.001 (3)
C8	0.046 (3)	0.050 (3)	0.046 (3)	0.003 (2)	0.002 (3)	0.003 (2)
C9	0.054 (4)	0.070 (4)	0.056 (4)	−0.001 (3)	0.015 (3)	−0.003 (3)
C10	0.074 (5)	0.073 (4)	0.051 (4)	0.006 (4)	0.008 (4)	−0.012 (4)
C11	0.072 (4)	0.061 (3)	0.054 (4)	−0.001 (4)	−0.018 (4)	0.000 (3)
C12	0.049 (3)	0.057 (3)	0.055 (4)	−0.001 (3)	−0.006 (3)	0.005 (3)
C13	0.045 (4)	0.048 (3)	0.053 (3)	0.004 (2)	0.004 (3)	0.004 (3)
C14	0.053 (4)	0.089 (4)	0.084 (5)	−0.008 (4)	−0.009 (4)	0.006 (4)
I1	0.0656 (3)	0.0895 (3)	0.0703 (3)	0.0186 (2)	0.0053 (3)	−0.0094 (3)
O1	0.049 (3)	0.088 (3)	0.057 (3)	−0.002 (2)	0.009 (2)	−0.007 (2)
N1	0.047 (2)	0.050 (2)	0.055 (3)	−0.0006 (18)	−0.001 (3)	0.002 (3)

Geometric parameters (Å, º) top

C1—C2	1.370 (10)	C8—C9	1.390 (9)
C1—C6	1.385 (9)	C8—C13	1.399 (8)
C1—I1	2.089 (6)	C9—C10	1.359 (10)
C2—C3	1.389 (11)	C9—H9	0.9300
C2—H2	0.9300	C10—C11	1.384 (10)
C3—C4	1.344 (11)	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.382 (9)
C4—C5	1.387 (10)	C11—H11	0.9300
C4—H4	0.9300	C12—C13	1.384 (8)
C5—C6	1.384 (8)	C12—C14	1.505 (9)
C5—H5	0.9300	C13—O1	1.352 (7)
C6—N1	1.401 (8)	C14—H14A	0.9600
C7—N1	1.286 (8)	C14—H14B	0.9600
C7—C8	1.451 (9)	C14—H14C	0.9600
C7—H7	0.9300	O1—H1	0.93 (7)

C2—C1—C6	121.4 (6)	C10—C9—C8	121.0 (6)
C2—C1—I1	119.0 (5)	C10—C9—H9	119.5
C6—C1—I1	119.6 (5)	C8—C9—H9	119.5
C1—C2—C3	119.6 (7)	C9—C10—C11	119.3 (7)
C1—C2—H2	120.2	C9—C10—H10	120.3
C3—C2—H2	120.2	C11—C10—H10	120.3
C4—C3—C2	120.0 (7)	C12—C11—C10	121.8 (7)
C4—C3—H3	120.0	C12—C11—H11	119.1
C2—C3—H3	120.0	C10—C11—H11	119.1
C3—C4—C5	120.7 (7)	C11—C12—C13	118.3 (6)
C3—C4—H4	119.7	C11—C12—C14	121.2 (6)
C5—C4—H4	119.7	C13—C12—C14	120.5 (6)
C6—C5—C4	120.5 (6)	O1—C13—C12	117.6 (5)
C6—C5—H5	119.7	O1—C13—C8	121.7 (6)
C4—C5—H5	119.7	C12—C13—C8	120.7 (6)
C5—C6—C1	117.8 (6)	C12—C14—H14A	109.5
C5—C6—N1	122.9 (6)	C12—C14—H14B	109.5
C1—C6—N1	119.2 (5)	H14A—C14—H14B	109.5
N1—C7—C8	122.8 (6)	C12—C14—H14C	109.5
N1—C7—H7	118.6	H14A—C14—H14C	109.5
C8—C7—H7	118.6	H14B—C14—H14C	109.5
C9—C8—C13	118.9 (6)	C13—O1—H1	109 (4)
C9—C8—C7	119.4 (6)	C7—N1—C6	121.0 (5)
C13—C8—C7	121.7 (6)

C6—C1—C2—C3	0.4 (10)	C8—C9—C10—C11	0.9 (10)
I1—C1—C2—C3	−179.2 (5)	C9—C10—C11—C12	−0.5 (10)
C1—C2—C3—C4	−0.9 (11)	C10—C11—C12—C13	0.8 (9)
C2—C3—C4—C5	0.9 (11)	C10—C11—C12—C14	179.6 (6)
C3—C4—C5—C6	−0.3 (11)	C11—C12—C13—O1	180.0 (5)
C4—C5—C6—C1	−0.3 (9)	C14—C12—C13—O1	1.2 (8)
C4—C5—C6—N1	−177.3 (6)	C11—C12—C13—C8	−1.4 (8)
C2—C1—C6—C5	0.2 (9)	C14—C12—C13—C8	179.8 (5)
I1—C1—C6—C5	179.8 (5)	C9—C8—C13—O1	−179.7 (5)
C2—C1—C6—N1	177.4 (5)	C7—C8—C13—O1	0.7 (8)
I1—C1—C6—N1	−3.1 (8)	C9—C8—C13—C12	1.7 (8)
N1—C7—C8—C9	−175.8 (6)	C7—C8—C13—C12	−177.9 (5)
N1—C7—C8—C13	3.8 (9)	C8—C7—N1—C6	175.4 (5)
C13—C8—C9—C10	−1.5 (9)	C5—C6—N1—C7	−33.7 (9)
C7—C8—C9—C10	178.2 (6)	C1—C6—N1—C7	149.2 (5)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C8–C13 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.93 (7)	1.82 (7)	2.634 (6)	144 (6)
C2—H2···Cg2ⁱ	0.93	2.97 (6)	3.7445 (4)	142 (4)

Symmetry code: (i) −x+1, y+1/2, −z+1/2.

Acknowledgements

This study was supported by Ondokuz Mayıs University under project No. PYO·FEN.1906.19.001.

Funding information

Funding for this research was provided by: Ondokuz Mayıs University (award No. PYO.FEN.1906.19.001).

References

Bernstein, J. L. (1967). Acta Cryst. 22, 747–748. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Bouhidel, Z., Cherouana, A., Durand, P., Doudouh, A., Morini, F., Guillot, B. & Dahaoui, S. (2018). Inorg. Chim. Acta, 482, 34–47. Web of Science CSD CrossRef CAS Google Scholar
Dominiak, P. M., Grech, E., Barr, G., Teat, S., Mallinson, P. & Woźniak, K. (2003). Chem. Eur. J. 9, 963–970. Web of Science CSD CrossRef PubMed CAS Google Scholar
Elmali, A. & Elerman, Y. (1997). Acta Cryst. C53, 791–793. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Faizi, M. S. H., Alagöz, T., Ahmed, R., Cinar, E. B., Agar, E., Dege, N. & Mashrai, A. (2020a). Acta Cryst. E76, 1146–1149. Web of Science CrossRef IUCr Journals Google Scholar
Faizi, M. S. H., Cinar, E. B., Aydin, A. S., Agar, E., Dege, N. & Mashrai, A. (2020b). Acta Cryst. E76, 1195–1200. CSD CrossRef IUCr Journals Google Scholar
Faizi, M. S. H., Cinar, E. B., Aydin, A. S., Agar, E., Dege, N. & Mashrai, A. (2020c). Acta Cryst. E76, 1320–1324. CSD CrossRef IUCr Journals Google Scholar
Faizi, M. S. H., Cinar, E. B., Dogan, O. E., Aydin, A. S., Agar, E., Dege, N. & Mashrai, A. (2020d). Acta Cryst. E76, 1325–1330. CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CrossRef IUCr Journals Google Scholar
Sahadevan, A. S., Cadoni, E., Monni, N., Sáenz de Pipaón, C., Galan Mascaros, J., Abhervé, A., Avarvari, N., Marchiò, L., Arca, M. & Mercuri, M. L. (2018). Cryst. Growth Des. 18, 4187–4199. Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Spackman, M. A. & Jayatilaka, D. (2009). CrystEngComm, 11, 19–32. Web of Science CrossRef CAS Google Scholar
Spek, A. L. (2020). Acta Cryst. E76, 1–11. Web of Science CrossRef IUCr Journals Google Scholar
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie GmbH, Darmstadt, Germany. Google Scholar
Turner, M. J., MacKinnon, J. J., Wolff, S. K., Grimwood, D. J., Spackman, P. R., Jayatilaka, D. & Spackman, M. A. (2017). Crystal Explorer 17.5. University of Western Australia. https://hirshfeldsurface.net. Google Scholar
Ünver, H. (2002). J. Mol. Struct. 641, 35–40. Web of Science CSD CrossRef Google Scholar
Vlad, A., Avadanei, M., Shova, S., Cazacu, M. & Zaltariov, M.-F. (2018). Polyhedron, 146, 129–135. Web of Science CSD CrossRef CAS Google Scholar
Wojciechowski, G., Przybylski, P., Schilf, W., Kamieński, B. & Brzezinski, B. (2003). J. Mol. Struct. 649, 197–205. Web of Science CrossRef CAS Google Scholar

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Volume 76| Part 10| October 2020| Pages 1595-1598

https://doi.org/10.1107/S2056989020011974

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

Crystal structure and Hirshfeld surface analysis of (E)-2-{[(2-iodo­phen­yl)imino]­meth­yl}-6-methyl­phenol

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Hirshfeld surface analysis

5. Database survey

6. Synthesis and crystallization

7. Refinement

Supporting information

Acknowledgements

Funding information

References

research communications

Crystal structure and Hirshfeld surface analysis of (E)-2-{[(2-iodophenyl)imino]methyl}-6-methylphenol

3. Supramolecular features