Crystal structure, DFT and MEP study of (E)-2-{[(3-chloro­phen­yl)imino]­meth­yl}-6-methyl­phenol

Saraçoğlu, H.; Doğan, O.E.; Ağar, T.; Dege, N.; Iskenderov, T.S.

doi:10.1107/S2056989019017353

research communications

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ISSN: 2056-9890

Volume 76| Part 2| February 2020| Pages 141-144

https://doi.org/10.1107/S2056989019017353

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Crystal structure, DFT and MEP study of (E)-2-{[(3-chlorophenyl)imino]methyl}-6-methylphenol

Hanife Saraçoğlu,^a ^* Onur Erman Doğan,^b Tuğgan Ağar,^c Necmi Dege ^d and Turganbay S. Iskenderov ^e ^*

^aOndokuz Mayıs University, Educational Faculty, Department of Mathematic and Science Education, 55139, Samsun, Turkey, ^bOndokuz Mayıs University, Faculty of Arts and Sciences, Department of Chemistry, 55139, Samsun, Turkey, ^cYeditepe University, Department of Chemical Engineering, 34755, Istanbul, Turkey, ^dOndokuz Mayıs University, Faculty of Arts and Sciences, Department of Physics, 55139, Samsun, Turkey, and ^eDepartment of Chemistry, Taras Shecchenko National University of Kyiv, 64, Vladimirska Str., Kiev 01601, Ukraine
^*Correspondence e-mail: hanifesa@omu.edu.tr, tiskenderov@ukr.net

Edited by J. T. Mague, Tulane University, USA (Received 17 December 2019; accepted 31 December 2019; online 7 January 2020)

In the crystal structure of the title compound, C₁₄H₁₂ClNO, the molecules are linked through C—H⋯O hydrogen bonds and C—H⋯π interactions, forming chains parallel to the [010] direction. π–π interactions and intramolecular hydrogen bonds are also observed. The molecular geometry of the title compound in the ground state has been calculated using density functional theory at the B3LYP level with the 6–311++G(2d,2p) basis set. Additionally, frontier molecular orbital and molecular electrostatic potential map analyses were performed.

Keywords: energy gap; Schiff base; anti-bacterial agent; frontier molecular orbitals; crystal structure.

CCDC reference: 1974885

1. Chemical context

Schiff bases, known as anils, imines or azomethines, have recently received considerable attention because of their good performance in coordination chemistry and anti-bacterial, anti-cancer and herbicidal applications (Piotr et al., 2009 ; Schiff, 1864 ). The presence of a lone pair of electrons in an sp²-hybridized orbital on the nitrogen atom of the azomethine group is of considerable chemical and biological importance (Sinha et al., 2008 ). In a continuation of our interest in the chemical, herbicidal and biological properties of Schiff bases we synthesized the title compound, (I), as a potential anti-bacterial agent (Yılmaz et al., 2012 ).

We report herein the synthesis, crystal structure and quantum chemical computational studies of the Schiff base compound, (I).

2. Structural commentary

The structure of the title compound (I) is shown in Fig. 1. It crystallizes in the orthorhombic space group Pbca with eight molecules in the unit cell. The molecular structure has two planar rings. The whole molecule is approximately planar, with a maximum deviation of −0.0236 (12) Å from planarity for the C8 atom of Schiff base. The title compound displays an E configuration with respect to the C8=N double bond. The dihedral angle between the two phenyl ring planes is 0.34 (9)° and the C5—C8—N1—C9 torsion angle is −179.81 (15)°. The planar molecular conformation is stabilized by the intramolecular O1—H1⋯N1 hydrogen bond, which forms an S(6) motif.

Figure 1
A view of the molecular structure of (I)

with the atom labelling. The dotted line indicates the intramolecular O—H⋯N hydrogen bond. Displacement ellipsoids are shown at the 40% probability level.

3. Supramolecular features

In the crystal, the molecules are linked by C10—H10⋯O1 hydrogen bonds (Table 1), generating a C₄⁴(16) chain running parallel to the [010] direction (Fig. 2). C—H⋯π interactions occur between the two phenyl rings (Fig. 3, Table 1). π–π stacking interactions [centroid–centroid distance = 3.6389 (11) Å] between the chlorophenyl and methylphenol rings are also observed.

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg are the centroids of the C1–C6 and C9–C14 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.88	2.605 (2)	148
C10—H10⋯O1ⁱ	0.93	2.56	3.402 (2)	151
C2—H2⋯Cg1ⁱⁱ	0.93	2.75	3.561 (2)	147
C12—H12⋯Cg2ⁱⁱⁱ	0.93	2.78	3.589 (2)	147
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z]$ ; (iii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

Figure 2
Diagram showing the hydrogen-bonding interactions in (I)

. Displacement ellipsoids are drawn at the 40% probability level. Symmetry code: (i) −x + 1, y + $[{1\over 2}]$ , −z + $[{1\over 2}]$ .

Figure 3
A partial packing diagram for (I)

showing the C—H⋯π interactions as dashed lines. Symmetry codes: (ii) −x + $[{3\over 2}]$ , y − $[{1\over 2}]$ , z; (iii) −x + $[{1\over 2}]$ , y + $[{1\over 2}]$ , z.. Cg1 and Cg2 are the centroids of the methylphenol and chlorophenyl rings, respectively.

4. Database survey

A search of the Cambridge Structural Database (CSD, version 5.40; update Nov. 2018; Groom et al., 2016 ) gave eighteen hits for the (E)-2-{[(3-chlorophenyl)imino]methyl}-6-methylphenol structure. With a value of 1.271 (2) Å, the N1—C8 bond in the title compound (I) is the same length within standard uncertainties as those in the structures of 2-[(E)-(5-chloro-2-methylphenyl)iminomethyl]-4-methylphenol (AFILAE; Zheng, 2013b ), 2,4-dibromo-6-{[(5-chloro-2-methylphenyl)imino]methyl}phenol (AGEGUQ; Zheng, 2013a ), 2-[(E)-(2,4,6-trichlorophenyl)iminomethyl]phenol (AWUSIV; Fun et al., 2011 ), N-(2-methyl-5-chlorophenyl)salicylaldimine (BEYQEB; Elmalı & Elerman, 1998 ), (E)-2-[(3-chlorophenylimino)methyl]-4-methoxyphenol (DUBNAQ; Özek et al., 2009 ), 3-{(E)-[(3,4-dichlorophenyl)imino]methyl}benzene-1,2-diol (MOYHAL; Tahir et al., 2015 ) and N-(3-chlorophenyl)salicylaldimine (NADZUO; Karakaş et al., 2004 ) where the C=N bond length varies from 1.266 (4) to 1.290 (3) Å. These structures also have an intramolecular O1—H1⋯N1 hydrogen bond resulting in the formation of a six-membered ring and exhibit an E configuration.

5. Frontier molecular orbital analysis

The frontier molecular orbitals are important in the determination of the optical, electronic and anti-corrosion properties of a molecular system (Koepnick et al., 2010 ; Solomon et al., 2012 ; Jafari et al., 2013 ). A molecule with a small frontier orbital gap is more polarizable than one with a large gap and is considered a soft molecule because of its high chemical reactivity and low kinetic stability (Prabavathi et al., 2015 ). The energy levels of the HOMO (highest occupied molecular orbital), HOMO-1, LUMO (lowest occupied molecular orbital) and LUMO+1 orbitals calculated at the B3LYP/6-311++G(2d,2p) level (Frisch et al., 2009 ; Dennington et al., 2007 ) for (I) are shown in Fig. 4. The HOMO, HOMO-1 and LUMO orbitals are delocalized over the two phenyl rings connected by a Schiff base bridge and HOMO and HOMO-1 can be said to be π-bonding orbitals. The LUMO+1 orbitals are delocalized on the chlorophenyl ring and the C atom of the Schiff base. LUMO and LUMO+1 orbitals exhibit π* antibonding character. The energy gap of (I) is 4.069 eV. The other molecular orbital energies are shown in Fig. 4. Electron affinity (A) and ionization potential (IP) can be defined as A = −E_LUMO and IP = −E_HOMO. Additionally, these values can also be used calculate the electronegativity (χ), chemical hardness (η) and chemical softness (S) (Prabavathi et al., 2015; Karunakaran & Balachandran, 2014 ). For the title compound (I), A = 2.201 eV, IP = 6.270 eV, χ = 4.236 eV, η = 2.035 eV, and S = 0.246 eV.

Figure 4
Plots of the frontier orbitals and the energy gap for (I)

6. Molecular electrostatic potential surface analysis

The analysis of a three-dimensional plot of the molecular electrostatic potential (MEP) surface is a technique for mapping the electrostatic potential onto the isoelectronic density surface, providing information about the reactive sites. The surface simultaneously displays molecular size and shape and the electrostatic potential value. In the colour scheme adopted, red indicates an electron-rich region with a partial negative charge and blue an electron-deficient region with partial positive charge, light blue indicates a slightly electron-deficient region, yellow a slightly electron-rich region and green a neutral region (Politzer et al., 2002 ). The MEP map of (I) was obtained by the B3LYP/6-311++G(2d,2p) method. In Fig. 5, it is shown that (I) has two possible sites of electrophilic attack. The negative region is localized on the protonated oxygen atom of methylphenol ring, O1, with a minimum value of −0.031 a.u. Positive potential sites of the compound are around hydrogen atoms. However, the maximum positive region is localized on the hydrogen atom bonded to the C atom forming the Schiff base, which can be considered as one possible site for nucleophilic attack, with a maximum value of 0.027 a.u.

Figure 5
Molecular electrostatic potential (MEP) map calculated at the B3LYP/6–311++G(2d,2p) level.

7. Synthesis and crystallization

A mixture of 2-hydroxy-3-methylbenzaldehyde (34.0 mg, 0.25 mmol) and 4-chloroaniline (31.9 mg, 0.25 mmol) was stirred with ethanol (30 mL) at 377 K for 4 h, affording the title compound (43.0 mg, yield 70%, m.p. 362–364 K). Single crystals suitable for X-ray measurements were obtained by recrystallization from methanol at room temperature.

8. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. H atoms were placed in calculated positions and refined using a riding model with C—H = 0.93–0.96 Å, U_iso(H) = 1.2–1.5U_eq(C).

Table 2
Experimental details

Crystal data
Chemical formula	C₁₄H₁₂ClNO
M_r	245.70
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	14.0717 (8), 6.4811 (4), 26.767 (2)
V (Å³)	2441.1 (3)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	0.29
Crystal size (mm)	0.45 × 0.43 × 0.38

Data collection
Diffractometer	Stoe IPDS 2
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002 )
T_min, T_max	0.820, 0.907
No. of measured, independent and observed [I > 2σ(I)] reflections	10011, 2052, 1669
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.586

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.117, 1.05
No. of reflections	2052
No. of parameters	155
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.24
Computer programs: X-AREA and X-RED32 (Stoe & Cie, 2002), SHELXT2018 (Sheldrick, 2015a ), SHELXL2018 (Sheldrick, 2015b ), ORTEP-3 for Windows and WinGX (Farrugia, 2012 ), Mercury (Macrae et al., 2006 ) and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1974885

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989019017353/mw2154sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989019017353/mw2154Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989019017353/mw2154Isup3.cml

checkCIF report

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXT2018 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: Mercury (Macrae et al., 2006), WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

(E)-2-{[(3-Chlorophenyl)imino]methyl}-6-methylphenol top

Crystal data top

C₁₄H₁₂ClNO	D_x = 1.337 Mg m⁻³
M_r = 245.70	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 15471 reflections
a = 14.0717 (8) Å	θ = 1.5–25.2°
b = 6.4811 (4) Å	µ = 0.29 mm⁻¹
c = 26.767 (2) Å	T = 296 K
V = 2441.1 (3) Å³	Prism, orange
Z = 8	0.45 × 0.43 × 0.38 mm
F(000) = 1024

Data collection top

Stoe IPDS 2 diffractometer	2052 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	1669 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.033
Detector resolution: 6.67 pixels mm^-1	θ_max = 24.6°, θ_min = 1.5°
rotation method scans	h = −16→16
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −6→7
T_min = 0.820, T_max = 0.907	l = −30→31
10011 measured reflections

Refinement top

Refinement on F²	Primary atom site location: other
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.039	H-atom parameters constrained
wR(F²) = 0.117	w = 1/[σ²(F_o²) + (0.0666P)² + 0.3364P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2052 reflections	Δρ_max = 0.16 e Å⁻³
155 parameters	Δρ_min = −0.24 e Å⁻³
0 restraints

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.

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

	x	y	z	U_iso*/U_eq
Cl1	0.33517 (5)	0.79127 (10)	0.03649 (2)	0.0888 (3)
C12	0.32979 (13)	0.7525 (3)	0.13616 (8)	0.0632 (5)
H12	0.296569	0.876559	0.136229	0.076*
C13	0.35979 (13)	0.6646 (3)	0.09213 (7)	0.0565 (5)
C11	0.35033 (14)	0.6518 (3)	0.18009 (8)	0.0655 (5)
H11	0.330163	0.707801	0.210266	0.079*
C14	0.40948 (13)	0.4816 (3)	0.09088 (7)	0.0554 (5)
H14	0.428370	0.425004	0.060536	0.067*
C9	0.43105 (12)	0.3826 (3)	0.13554 (6)	0.0501 (4)
C10	0.40037 (13)	0.4690 (3)	0.18002 (7)	0.0581 (5)
H10	0.413635	0.403110	0.210087	0.070*
C8	0.51952 (12)	0.1055 (3)	0.10169 (7)	0.0533 (4)
H8	0.511386	0.163728	0.070226	0.064*
N1	0.48348 (10)	0.1964 (2)	0.13929 (5)	0.0524 (4)
C4	0.60571 (14)	−0.1837 (3)	0.06298 (7)	0.0617 (5)
H4	0.594284	−0.124767	0.031869	0.074*
C5	0.57270 (12)	−0.0849 (3)	0.10589 (6)	0.0507 (4)
C3	0.65470 (14)	−0.3660 (3)	0.06587 (8)	0.0658 (5)
H3	0.676683	−0.430204	0.037024	0.079*
C6	0.59085 (12)	−0.1759 (3)	0.15252 (6)	0.0511 (4)
O1	0.56117 (10)	−0.0861 (2)	0.19521 (4)	0.0668 (4)
H1	0.533250	0.021525	0.188623	0.100*
C2	0.67106 (13)	−0.4535 (3)	0.11231 (8)	0.0631 (5)
H2	0.703893	−0.577825	0.114078	0.076*
C1	0.64031 (13)	−0.3625 (3)	0.15602 (7)	0.0563 (5)
C7	0.65775 (16)	−0.4616 (4)	0.20614 (9)	0.0763 (6)
H7A	0.694377	−0.585261	0.201724	0.114*
H7B	0.598004	−0.495240	0.221426	0.114*
H7C	0.691973	−0.367515	0.227197	0.114*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1145 (5)	0.0730 (4)	0.0790 (4)	0.0241 (3)	−0.0112 (3)	0.0176 (3)
C12	0.0587 (11)	0.0503 (11)	0.0807 (15)	0.0027 (9)	0.0037 (9)	−0.0065 (10)
C13	0.0583 (10)	0.0475 (11)	0.0637 (11)	0.0008 (8)	−0.0049 (8)	0.0044 (9)
C11	0.0684 (12)	0.0645 (13)	0.0635 (12)	0.0014 (10)	0.0096 (9)	−0.0150 (10)
C14	0.0651 (11)	0.0511 (11)	0.0502 (10)	0.0032 (9)	−0.0001 (8)	0.0002 (8)
C9	0.0527 (9)	0.0450 (10)	0.0526 (9)	−0.0037 (8)	−0.0025 (7)	0.0014 (8)
C10	0.0644 (11)	0.0594 (12)	0.0506 (10)	−0.0040 (9)	0.0028 (8)	−0.0030 (9)
C8	0.0620 (11)	0.0483 (10)	0.0498 (9)	−0.0007 (8)	−0.0023 (8)	0.0062 (8)
N1	0.0595 (9)	0.0461 (9)	0.0517 (8)	0.0007 (7)	−0.0021 (6)	0.0006 (7)
C4	0.0693 (11)	0.0610 (13)	0.0546 (11)	0.0007 (10)	0.0075 (9)	0.0022 (9)
C5	0.0545 (9)	0.0454 (10)	0.0520 (10)	−0.0020 (8)	0.0018 (7)	0.0011 (8)
C3	0.0676 (12)	0.0597 (12)	0.0702 (13)	0.0030 (10)	0.0129 (9)	−0.0078 (10)
C6	0.0532 (9)	0.0483 (11)	0.0518 (10)	−0.0016 (8)	−0.0018 (7)	0.0006 (8)
O1	0.0889 (10)	0.0615 (9)	0.0500 (7)	0.0148 (7)	−0.0033 (6)	0.0003 (6)
C2	0.0545 (10)	0.0492 (11)	0.0854 (14)	0.0022 (8)	0.0064 (9)	0.0017 (10)
C1	0.0521 (9)	0.0512 (11)	0.0655 (11)	−0.0010 (8)	−0.0028 (8)	0.0064 (9)
C7	0.0836 (15)	0.0674 (14)	0.0779 (14)	0.0115 (11)	−0.0107 (11)	0.0173 (11)

Geometric parameters (Å, º) top

Cl1—C13	1.7357 (19)	C4—C3	1.370 (3)
C12—C13	1.375 (3)	C4—C5	1.395 (2)
C12—C11	1.376 (3)	C4—H4	0.9300
C12—H12	0.9300	C5—C6	1.404 (2)
C13—C14	1.377 (3)	C3—C2	1.386 (3)
C11—C10	1.378 (3)	C3—H3	0.9300
C11—H11	0.9300	C6—O1	1.348 (2)
C14—C9	1.390 (2)	C6—C1	1.399 (3)
C14—H14	0.9300	O1—H1	0.8200
C9—C10	1.385 (2)	C2—C1	1.380 (3)
C9—N1	1.418 (2)	C2—H2	0.9300
C10—H10	0.9300	C1—C7	1.507 (3)
C8—N1	1.271 (2)	C7—H7A	0.9600
C8—C5	1.448 (2)	C7—H7B	0.9600
C8—H8	0.9300	C7—H7C	0.9600

C13—C12—C11	118.11 (18)	C5—C4—H4	119.4
C13—C12—H12	120.9	C4—C5—C6	118.61 (16)
C11—C12—H12	120.9	C4—C5—C8	119.96 (16)
C12—C13—C14	122.25 (18)	C6—C5—C8	121.42 (16)
C12—C13—Cl1	118.56 (15)	C4—C3—C2	119.16 (19)
C14—C13—Cl1	119.19 (15)	C4—C3—H3	120.4
C12—C11—C10	120.94 (18)	C2—C3—H3	120.4
C12—C11—H11	119.5	O1—C6—C1	118.05 (15)
C10—C11—H11	119.5	O1—C6—C5	121.05 (16)
C13—C14—C9	119.17 (17)	C1—C6—C5	120.90 (16)
C13—C14—H14	120.4	C6—O1—H1	109.5
C9—C14—H14	120.4	C1—C2—C3	122.26 (18)
C10—C9—C14	118.98 (17)	C1—C2—H2	118.9
C10—C9—N1	116.45 (16)	C3—C2—H2	118.9
C14—C9—N1	124.57 (16)	C2—C1—C6	117.95 (17)
C11—C10—C9	120.54 (18)	C2—C1—C7	121.44 (18)
C11—C10—H10	119.7	C6—C1—C7	120.61 (17)
C9—C10—H10	119.7	C1—C7—H7A	109.5
N1—C8—C5	122.65 (16)	C1—C7—H7B	109.5
N1—C8—H8	118.7	H7A—C7—H7B	109.5
C5—C8—H8	118.7	C1—C7—H7C	109.5
C8—N1—C9	123.07 (15)	H7A—C7—H7C	109.5
C3—C4—C5	121.12 (18)	H7B—C7—H7C	109.5
C3—C4—H4	119.4

C11—C12—C13—C14	−0.3 (3)	N1—C8—C5—C4	176.22 (18)
C11—C12—C13—Cl1	−179.48 (15)	N1—C8—C5—C6	−2.7 (3)
C13—C12—C11—C10	0.6 (3)	C5—C4—C3—C2	0.3 (3)
C12—C13—C14—C9	−0.6 (3)	C4—C5—C6—O1	179.49 (16)
Cl1—C13—C14—C9	178.56 (14)	C8—C5—C6—O1	−1.6 (3)
C13—C14—C9—C10	1.2 (3)	C4—C5—C6—C1	−0.5 (3)
C13—C14—C9—N1	−178.54 (16)	C8—C5—C6—C1	178.43 (16)
C12—C11—C10—C9	−0.1 (3)	C4—C3—C2—C1	−0.5 (3)
C14—C9—C10—C11	−0.9 (3)	C3—C2—C1—C6	0.2 (3)
N1—C9—C10—C11	178.88 (16)	C3—C2—C1—C7	179.21 (19)
C5—C8—N1—C9	−179.81 (15)	O1—C6—C1—C2	−179.65 (16)
C10—C9—N1—C8	−176.76 (17)	C5—C6—C1—C2	0.3 (3)
C14—C9—N1—C8	3.0 (3)	O1—C6—C1—C7	1.3 (3)
C3—C4—C5—C6	0.2 (3)	C5—C6—C1—C7	−178.70 (17)
C3—C4—C5—C8	−178.79 (17)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg are the centroids of the C1–C6 and C9–C14 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.88	2.605 (2)	148
C10—H10···O1ⁱ	0.93	2.56	3.402 (2)	151
C2—H2···Cg1ⁱⁱ	0.93	2.75	3.561 (2)	147
C12—H12···Cg2ⁱⁱⁱ	0.93	2.78	3.589 (2)	147

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

Funding information

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

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Volume 76| Part 2| February 2020| Pages 141-144

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

Crystal structure, DFT and MEP study of (E)-2-{[(3-chloro­phen­yl)imino]­meth­yl}-6-methyl­phenol

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Database survey

5. Frontier mol­ecular orbital analysis

6. Mol­ecular electrostatic potential surface analysis

7. Synthesis and crystallization

8. Refinement

Supporting information

Funding information

References

research communications

Crystal structure, DFT and MEP study of (E)-2-{[(3-chlorophenyl)imino]methyl}-6-methylphenol

3. Supramolecular features

5. Frontier molecular orbital analysis

6. Molecular electrostatic potential surface analysis