(E)-2-{[(4-Anilinophen­yl)imino]­meth­yl}-4-bromo-5-fluoro­phenol

Kalecik, S.; Yavuz, M.; Kavraz, F.; Eserci, H.; Ağar, E.

doi:10.1107/S2414314617017084

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 12| December 2017| x171708

https://doi.org/10.1107/S2414314617017084

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(E)-2-{[(4-Anilinophenyl)imino]methyl}-4-bromo-5-fluorophenol

Sedanur Kalecik,^a Metin Yavuz,^a ^* Fatih Kavraz,^b Hande Eserci ^c and Erbil Ağar ^b

^aDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, TR-55139, Samsun, Turkey, ^bDepartment of Chemistry, Faculty of Arts and Sciences, Ondokuz Mayıs University, Kurupelit, 55139 Samsun, Turkey, and ^cDepartment of Chemistry, Faculty of Arts and Sciences, Gebze University, Gebze, 41400 Kocaeli, Turkey
^*Correspondence e-mail: myavuz@omu.edu.tr

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 21 November 2017; accepted 27 November 2017; online 8 December 2017)

In the title compound, C₁₉H₁₄BrFN₂O, the dihedral angles between the central benzene ring and the pendant trisubstituted ring and phenyl group are 25.7 (2) and 51.7 (2)°, respectively. The molecular conformation is influenced by an intramolecular O—H⋯N hydrogen bond. In the crystal, N—H⋯O hydrogen bonds link molecules into C(11) chains propagating in [100] and weak aromatic π–π stacking is also observed [centroid–centroid separation = 3.682 (3) Å]

Keywords: crystal structure; Schiff base; hydrogen bonding.

CCDC reference: 1587779

Structure description

Schiff bases (Schiff, 1864 ) contain the azomethine grouping (–RC=N–) and are prepared by condensation reactions between amines and active carbonyl compounds. As part of our studies in this area, we herein report the synthesis and structure of the title compound (Fig. 1).

Figure 1
A view of the title compound with 50% probability displacement ellipsoids. The intramolecular O—H⋯N hydrogen bond is indicated by a dashed line.

The dihedral angles between the central benzene ring (C8–C13) and pendant trisubstituted ring (C1–C6) and phenyl ring (C14–C19) are 25.7 (2) and 51.7 (2)°, respectively; the dihedral angle between the outer rings is 75.9 (2)°. The molecular conformation is influenced by an intramolecular O—H⋯N hydrogen bond (Table 1, Fig. 1), which generates an S(6) ring. The bond lengths for imino group atoms [N2—C8 = 1.403 (5) and N2—C7 = 1.292 (5) Å] are consistent with those in related structures such as 2-amino-3-((E)-{[3-(trifluoromethyl)phenyl]imino}methyl)-4H-chromen-4-one (Atalay et al., 2016 ) and (Z)-4-{[(Z)-(2-oxonaphthalen-1(2H)- ylidene)methyl]amino}-N-(thiazol-2(3H)-ylidene)benzenesulfonamide (Köysal et al., 2015 ).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H01⋯N2	0.82	1.80	2.535 (4)	149
N1—H02⋯O1ⁱ	0.84 (4)	2.11 (4)	2.927 (5)	166 (4)
Symmetry code: (i) $[x-{\script{1\over 2}}, y, -z+{\script{3\over 2}}]$ .

In the extended structure (Fig. 2), N—H⋯O hydrogen bonds link the molecules into C(11) chains propagating in [100]; thus O1 serves as an acceptor for both intra- and intermolecular hydrogen bonds. Weak aromatic π–π stacking between the C1–C6 rings is also observed [centroid–centroid separation = 3.682 (3) Å]

Figure 2
A partial packing view. Dashed lines indicate the hydrogen bonds.

Synthesis and crystallization

The title compound was prepared by refluxing for 18 h a mixture of 5-bromo-3-fluoro-2-hydroxybenzaldehyde (0.01 g, 0.045 mmol) in 20 ml ethyl alcohol and N-phenylbenzene-1,4-diamine (0.08 g, 0.045 mmol) in 20 ml ethyl alcohol. Red prismatic crystals were obtained from the solution by slow evaporation (yield 73%; m.p. 168–170°C).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₉H₁₄BrFN₂O
M_r	385.23
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	13.4521 (15), 7.1810 (7), 34.204 (3)
V (Å³)	3304.1 (6)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	2.51
Crystal size (mm)	0.40 × 0.25 × 0.07

Data collection
Diffractometer	Agilent Xcalibur Eos
Absorption correction	Analytical (CrysAlis PRO; Rigaku, 2015 $[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction Ltd, Yarnton, England.]$ )
T_min, T_max	0.495, 0.896
No. of measured, independent and observed [I > 2σ(I)] reflections	6640, 3349, 1552
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.110, 0.97
No. of reflections	3349
No. of parameters	221
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.51
Computer programs: CrysAlis PRO (Rigaku OD, 2015 $[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction Ltd, Yarnton, England.]$ ), SHELXS97 (Sheldrick, 2008 ), SHELXL2016 (Sheldrick, 2015 ) and ORTEP-3 for Windows (Farrugia, 2012 ).

Structural data

CCDC reference: 1587779

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314617017084/hb4185sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617017084/hb4185Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617017084/hb4185Isup3.cml

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL2016 (Sheldrick, 2015).

(I) top

Crystal data top

C₁₉H₁₄BrFN₂O	D_x = 1.549 Mg m⁻³
M_r = 385.23	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 1184 reflections
a = 13.4521 (15) Å	θ = 3.8–20.9°
b = 7.1810 (7) Å	µ = 2.51 mm⁻¹
c = 34.204 (3) Å	T = 293 K
V = 3304.1 (6) Å³	Prism, red
Z = 8	0.40 × 0.25 × 0.07 mm
F(000) = 1552

Data collection top

Agilent Xcalibur Eos diffractometer	R_int = 0.052
Radiation source: fine-focus sealed X-ray tube	θ_max = 26.4°, θ_min = 3.0°
w scans	h = −16→9
Absorption correction: analytical (CrysAlis PRO; Rigaku, 2015)	k = −4→8
T_min = 0.495, T_max = 0.896	l = −36→42
6640 measured reflections	6678 standard reflections every ··· reflections
3349 independent reflections	intensity decay: ···
1552 reflections with I > 2σ(I)

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.055	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.110	w = 1/[σ²(F_o²) + (0.0267P)²] where P = (F_o² + 2F_c²)/3
S = 0.97	(Δ/σ)_max = 0.001
3349 reflections	Δρ_max = 0.35 e Å⁻³
221 parameters	Δρ_min = −0.51 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.

Refinement. The N—H and H atoms were located in a difference Fourier map. Their positional and isotropic thermal parameters were included in further stages of the refinement. All C-bound H atoms were positioned geometricaly and refined using a riding model with C—H = 0.93 - 0.97 Å and with U_iso(H) = 1.2 - 1.5 U_eq(C).

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

	x	y	z	U_iso*/U_eq
Br1	0.65808 (5)	0.86784 (8)	0.50622 (2)	0.0847 (3)
F1	0.8795 (2)	0.8762 (4)	0.52160 (8)	0.0843 (9)
O1	0.88602 (19)	0.6698 (4)	0.65086 (9)	0.0586 (9)
H01	0.848013	0.636740	0.668277	0.088*
N2	0.7227 (2)	0.6000 (4)	0.68480 (10)	0.0403 (9)
N1	0.5591 (3)	0.4382 (6)	0.83117 (12)	0.0542 (12)
C8	0.6757 (3)	0.5548 (5)	0.72019 (12)	0.0366 (10)
C3	0.7295 (3)	0.7032 (6)	0.61908 (13)	0.0398 (11)
C7	0.6765 (3)	0.6471 (5)	0.65320 (13)	0.0414 (11)
H7	0.607388	0.644255	0.652690	0.050*
C11	0.5987 (3)	0.4717 (6)	0.79440 (13)	0.0411 (11)
C13	0.5808 (3)	0.6124 (6)	0.73096 (13)	0.0460 (12)
H13	0.541659	0.677957	0.713265	0.055*
C9	0.7308 (3)	0.4599 (5)	0.74768 (13)	0.0410 (11)
H9	0.795425	0.424950	0.741439	0.049*
C4	0.6786 (3)	0.7504 (6)	0.58495 (13)	0.0470 (12)
H4	0.609510	0.744233	0.584742	0.056*
C5	0.7267 (4)	0.8051 (6)	0.55214 (13)	0.0499 (12)
C10	0.6941 (3)	0.4148 (5)	0.78392 (13)	0.0429 (11)
H10	0.732748	0.346709	0.801366	0.052*
C12	0.5448 (3)	0.5731 (6)	0.76728 (13)	0.0472 (12)
H12	0.481906	0.615940	0.774085	0.057*
C2	0.8344 (3)	0.7128 (6)	0.61936 (13)	0.0432 (11)
C14	0.5920 (3)	0.3098 (7)	0.85908 (13)	0.0452 (12)
C6	0.8301 (5)	0.8171 (6)	0.55333 (15)	0.0577 (14)
C15	0.6228 (3)	0.1338 (7)	0.84917 (15)	0.0565 (13)
H15	0.625653	0.098961	0.823011	0.068*
C1	0.8829 (3)	0.7725 (6)	0.58571 (16)	0.0555 (14)
H1	0.951815	0.781849	0.585443	0.067*
C19	0.5873 (3)	0.3579 (8)	0.89792 (14)	0.0636 (14)
H19	0.566809	0.477105	0.904875	0.076*
C16	0.6498 (3)	0.0081 (8)	0.87793 (18)	0.0733 (16)
H16	0.671249	−0.110613	0.871086	0.088*
C17	0.6449 (4)	0.0586 (9)	0.91645 (18)	0.0784 (18)
H17	0.663745	−0.025643	0.935727	0.094*
C18	0.6125 (4)	0.2322 (10)	0.92675 (16)	0.0824 (18)
H18	0.607576	0.265250	0.952963	0.099*
H02	0.516 (3)	0.515 (5)	0.8390 (13)	0.049 (16)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.1416 (6)	0.0693 (4)	0.0432 (3)	0.0091 (4)	−0.0233 (3)	0.0049 (3)
F1	0.127 (2)	0.078 (2)	0.0485 (19)	−0.0068 (18)	0.0331 (17)	0.0069 (18)
O1	0.0495 (19)	0.083 (2)	0.044 (2)	0.0085 (18)	−0.0003 (15)	0.007 (2)
N2	0.052 (2)	0.036 (2)	0.033 (2)	0.0052 (19)	0.0005 (18)	0.0016 (19)
N1	0.058 (3)	0.068 (3)	0.037 (2)	0.024 (3)	0.011 (2)	0.004 (2)
C8	0.047 (3)	0.031 (2)	0.032 (3)	−0.001 (2)	−0.002 (2)	0.001 (2)
C3	0.048 (3)	0.035 (3)	0.037 (3)	−0.002 (2)	0.001 (2)	0.000 (2)
C7	0.042 (3)	0.038 (3)	0.044 (3)	0.001 (2)	0.002 (2)	−0.002 (2)
C11	0.043 (3)	0.043 (3)	0.038 (3)	−0.002 (2)	0.004 (2)	−0.003 (2)
C13	0.045 (3)	0.049 (3)	0.044 (3)	0.007 (3)	−0.003 (2)	0.007 (3)
C9	0.037 (3)	0.041 (3)	0.045 (3)	0.007 (2)	0.002 (2)	−0.006 (2)
C4	0.062 (3)	0.038 (3)	0.041 (3)	0.008 (3)	−0.001 (2)	−0.003 (2)
C5	0.076 (4)	0.038 (3)	0.036 (3)	0.011 (3)	−0.005 (3)	−0.003 (2)
C10	0.047 (3)	0.045 (3)	0.037 (3)	0.004 (2)	−0.003 (2)	0.003 (2)
C12	0.048 (3)	0.049 (3)	0.045 (3)	0.012 (2)	0.002 (2)	0.009 (3)
C2	0.051 (3)	0.037 (3)	0.042 (3)	0.003 (3)	0.002 (2)	−0.004 (2)
C14	0.036 (3)	0.067 (4)	0.032 (3)	0.000 (3)	−0.002 (2)	0.005 (3)
C6	0.103 (5)	0.032 (3)	0.038 (3)	0.005 (3)	0.021 (3)	−0.002 (2)
C15	0.057 (3)	0.067 (4)	0.045 (3)	0.009 (3)	0.005 (2)	0.007 (3)
C1	0.061 (3)	0.048 (3)	0.057 (4)	0.003 (3)	0.022 (3)	0.004 (3)
C19	0.069 (3)	0.079 (4)	0.043 (3)	0.004 (3)	0.000 (3)	−0.002 (3)
C16	0.066 (3)	0.081 (4)	0.073 (4)	0.018 (3)	0.005 (3)	0.020 (4)
C17	0.081 (4)	0.103 (5)	0.051 (4)	0.009 (4)	−0.004 (3)	0.031 (4)
C18	0.085 (4)	0.125 (6)	0.037 (4)	0.000 (4)	−0.006 (3)	0.004 (4)

Geometric parameters (Å, º) top

Br1—C5	1.877 (5)	C9—H9	0.9300
F1—C6	1.341 (5)	C4—C5	1.354 (6)
O1—C2	1.318 (5)	C4—H4	0.9300
O1—H01	0.8200	C5—C6	1.394 (6)
N2—C7	1.292 (5)	C10—H10	0.9300
N2—C8	1.403 (5)	C12—H12	0.9300
N1—C11	1.387 (5)	C2—C1	1.390 (6)
N1—C14	1.399 (5)	C14—C15	1.373 (6)
N1—H02	0.84 (4)	C14—C19	1.374 (6)
C8—C9	1.378 (5)	C6—C1	1.354 (6)
C8—C13	1.392 (5)	C15—C16	1.384 (6)
C3—C4	1.396 (5)	C15—H15	0.9300
C3—C2	1.413 (5)	C1—H1	0.9300
C3—C7	1.426 (5)	C19—C18	1.380 (7)
C7—H7	0.9300	C19—H19	0.9300
C11—C12	1.385 (5)	C16—C17	1.368 (7)
C11—C10	1.394 (5)	C16—H16	0.9300
C13—C12	1.363 (5)	C17—C18	1.367 (7)
C13—H13	0.9300	C17—H17	0.9300
C9—C10	1.372 (5)	C18—H18	0.9300

C2—O1—H01	109.5	C11—C10—H10	120.2
C7—N2—C8	124.4 (4)	C13—C12—C11	122.2 (4)
C11—N1—C14	127.7 (4)	C13—C12—H12	118.9
C11—N1—H02	116 (3)	C11—C12—H12	118.9
C14—N1—H02	116 (3)	O1—C2—C1	120.1 (4)
C9—C8—C13	117.4 (4)	O1—C2—C3	121.3 (4)
C9—C8—N2	117.5 (4)	C1—C2—C3	118.5 (4)
C13—C8—N2	124.9 (4)	C15—C14—C19	118.9 (5)
C4—C3—C2	119.0 (4)	C15—C14—N1	122.3 (4)
C4—C3—C7	120.5 (4)	C19—C14—N1	118.7 (5)
C2—C3—C7	120.5 (4)	F1—C6—C1	118.5 (5)
N2—C7—C3	121.2 (4)	F1—C6—C5	119.4 (5)
N2—C7—H7	119.4	C1—C6—C5	122.2 (5)
C3—C7—H7	119.4	C14—C15—C16	120.3 (5)
C12—C11—N1	119.8 (4)	C14—C15—H15	119.8
C12—C11—C10	117.7 (4)	C16—C15—H15	119.8
N1—C11—C10	122.4 (4)	C6—C1—C2	120.3 (5)
C12—C13—C8	120.4 (4)	C6—C1—H1	119.9
C12—C13—H13	119.8	C2—C1—H1	119.9
C8—C13—H13	119.8	C14—C19—C18	121.0 (5)
C10—C9—C8	122.7 (4)	C14—C19—H19	119.5
C10—C9—H9	118.7	C18—C19—H19	119.5
C8—C9—H9	118.7	C17—C16—C15	119.9 (6)
C5—C4—C3	121.9 (4)	C17—C16—H16	120.0
C5—C4—H4	119.0	C15—C16—H16	120.0
C3—C4—H4	119.0	C18—C17—C16	120.4 (6)
C4—C5—C6	118.1 (5)	C18—C17—H17	119.8
C4—C5—Br1	121.9 (4)	C16—C17—H17	119.8
C6—C5—Br1	120.0 (4)	C17—C18—C19	119.4 (6)
C9—C10—C11	119.6 (4)	C17—C18—H18	120.3
C9—C10—H10	120.2	C19—C18—H18	120.3

C7—N2—C8—C9	162.7 (4)	C7—C3—C2—O1	0.3 (6)
C7—N2—C8—C13	−23.2 (7)	C4—C3—C2—C1	1.2 (6)
C8—N2—C7—C3	175.8 (4)	C7—C3—C2—C1	−178.5 (4)
C4—C3—C7—N2	178.9 (4)	C11—N1—C14—C15	−40.7 (7)
C2—C3—C7—N2	−1.5 (6)	C11—N1—C14—C19	143.4 (5)
C14—N1—C11—C12	165.8 (4)	C4—C5—C6—F1	−178.0 (4)
C14—N1—C11—C10	−17.5 (7)	Br1—C5—C6—F1	0.9 (6)
C9—C8—C13—C12	−0.7 (6)	C4—C5—C6—C1	1.4 (7)
N2—C8—C13—C12	−174.8 (4)	Br1—C5—C6—C1	−179.7 (4)
C13—C8—C9—C10	2.7 (6)	C19—C14—C15—C16	−0.7 (7)
N2—C8—C9—C10	177.3 (4)	N1—C14—C15—C16	−176.6 (4)
C2—C3—C4—C5	0.0 (7)	F1—C6—C1—C2	179.3 (4)
C7—C3—C4—C5	179.7 (4)	C5—C6—C1—C2	−0.2 (7)
C3—C4—C5—C6	−1.3 (7)	O1—C2—C1—C6	−179.9 (4)
C3—C4—C5—Br1	179.8 (3)	C3—C2—C1—C6	−1.1 (7)
C8—C9—C10—C11	−2.3 (6)	C15—C14—C19—C18	−0.4 (7)
C12—C11—C10—C9	−0.2 (6)	N1—C14—C19—C18	175.7 (4)
N1—C11—C10—C9	−176.9 (4)	C14—C15—C16—C17	0.6 (7)
C8—C13—C12—C11	−1.8 (7)	C15—C16—C17—C18	0.7 (8)
N1—C11—C12—C13	179.0 (4)	C16—C17—C18—C19	−1.7 (8)
C10—C11—C12—C13	2.2 (7)	C14—C19—C18—C17	1.6 (8)
C4—C3—C2—O1	179.9 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H01···N2	0.82	1.80	2.535 (4)	149
N1—H02···O1ⁱ	0.84 (4)	2.11 (4)	2.927 (5)	166 (4)

Symmetry code: (i) x−1/2, y, −z+3/2.

Acknowledgements

The authors thank Dokuz Eylül University, Faculty of Sciences, Department of Physics, and Assistant Professor Muhittin Aygün for the data collection.

Funding information

Funding for this research was provided by: Ondokuz Mayis University (research grant PYO.FEN.1904.17.006[D16]).

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