(E)-4-Bromo-5-meth­oxy-2-{[(2-meth­oxy­phen­yl)imino]­meth­yl}phenol monohydrate

Atalay, Ş.; Aygün, S.N.; Meral, S.; Ağar, E.

doi:10.1107/S2414314617017308

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 12| December 2017| x171730

https://doi.org/10.1107/S2414314617017308

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(E)-4-Bromo-5-methoxy-2-{[(2-methoxyphenyl)imino]methyl}phenol monohydrate

Şehriman Atalay,^a ^* Seda Nur Aygün,^b Seher Meral ^b and Erbil Ağar ^b

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

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 2 December 2017; accepted 2 December 2017; online 8 December 2017)

In the title Schiff base hydrate, C₁₅H₁₄BrNO₃·H₂O, the dihedral angle between the benzene rings is 0.9 (2)° and an intramolecular O—H⋯N hydrogen bond closes an S(6) ring. In the crystal, O_w—H⋯O (w = water) hydrogen bonds link the components into centrosymmetric tetramers (two Schiff bases and two water molecules). Weak C—H⋯O_w interactions consolidate the linking of the molecules within the tetramers. The O atom of the water molecule is disordered over two adjacent sites in a 0.73 (9):0.27 (9) ratio.

Keywords: crystal structure; Schiff base; hydrogen bonding; centrosymmetric tetramer.

CCDC reference: 1588757

Structure description

As part of our ongoing studies of Schiff bases (Köysal et al., 2015 ), we now describe the synthesis and structure of the title compound (Fig. 1), which crystallizes as a monohydrate.

Figure 1
A view of the title compound, with 50% probability displacement ellipsoids. Intramolecular hydrogen bonds and bonds to the solvate water molecule in the asymmetric unit are drawn as double dashed lines.

The dihedral angle between the C2–C7 and C9–C14 benzene rings is 0.9 (2)° and the entire molecule is almost planar (r.m.s. deviation for all non-H atoms = 0.018 Å) The bond distances of imino group atoms [N1—C8 = 1.306 (4); N1—C9 = 1.415 (5) Å] are consistent with those in related structures (Köysal et al., 2015). An intramolecular O—H⋯N hydrogen bond closes an S(6) ring (Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1	0.82	2.64	3.340 (4)	144
O2—H2⋯N1	0.82	1.84	2.581 (4)	149
O4B—H4A⋯O2ⁱ	0.86	2.01	2.85 (2)	166
O4B—H4B⋯O2ⁱⁱ	0.77	2.23	2.99 (3)	170
C8—H8⋯O4B	0.93	2.44	3.18 (2)	136
C10—H10⋯O4A	0.93	2.56	3.31 (6)	138
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y+1, -z+1.

In the crystal (Fig. 2), O_w—H⋯O (w = water) hydrogen bonds link the components into centrosymmetric tetramers (two Schiff bases and two water molecules). Weak C—H⋯O_w interactions are also observed (Table 1).

Figure 2
The packing, viewed along the bc plane showing the hydrogen-bonding interactions.

Synthesis and crystallization

Solutions of 5-bromo-2-hydroxy-4-methoxybenzaldehyde (0.0154 g, 0.066 mmol) in 20 ml ethanol and 2-methoxyaniline (0.0071 g, 0.066 mmol) in 20 ml ethanol were mixed and stirred for 18 h under reflux. Yellow prisms of the title compound were obtained from ethanol solution by slow evaporation (yield 67%; m.p. 401–405 K).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The O atom of the water molecule of crystallization is disordered over two adjacent sites in a 0.73 (9):0.27 (9) ratio.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₅H₁₄BrNO₃·H₂O
M_r	354.20
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	293
a, b, c (Å)	6.922 (3), 8.498 (3), 14.064 (5)
α, β, γ (°)	78.30 (3), 85.51 (3), 69.10 (3)
V (Å³)	756.8 (6)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	2.73
Crystal size (mm)	0.79 × 0.39 × 0.07

Data collection
Diffractometer	Stoe IPDS 2
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002 )
T_min, T_max	0.115, 0.755
No. of measured, independent and observed [I > 2σ(I)] reflections	11464, 3139, 2179
R_int	0.124
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.131, 0.98
No. of reflections	3139
No. of parameters	206
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.73, −0.53
Computer programs: X-AREA (Stoe & Cie, 2002), SHELXT2016 (Sheldrick, 2015a ), SHELXL2016 (Sheldrick, 2015b ), ORTEP-3 for Windows and WinGX (Farrugia, 2012 ) and PLATON (Spek, 2009 ).

Structural data

CCDC reference: 1588757

Crystal structure: contains datablocks hakan12, I. DOI: https://doi.org/10.1107/S2414314617017308/hb4187sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617017308/hb4187Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617017308/hb4187Isup3.cml

checkCIF report

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-AREA (Stoe & Cie, 2002); program(s) used to solve structure: SHELXT2016 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

(E)-4-Bromo-5-methoxy-2-{[(2-methoxyphenyl)imino]methyl}phenol monohydrate top

Crystal data top

C₁₅H₁₄BrNO₃·H₂O	Z = 2
M_r = 354.20	F(000) = 360
Triclinic, P1	D_x = 1.554 Mg m⁻³
a = 6.922 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.498 (3) Å	Cell parameters from 11116 reflections
c = 14.064 (5) Å	θ = 1.5–27.6°
α = 78.30 (3)°	µ = 2.73 mm⁻¹
β = 85.51 (3)°	T = 293 K
γ = 69.10 (3)°	Prism, yellow
V = 756.8 (6) Å³	0.79 × 0.39 × 0.07 mm

Data collection top

Stoe IPDS 2 diffractometer	2179 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm^-1	R_int = 0.124
rotation method scans	θ_max = 26.5°, θ_min = 1.5°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −8→8
T_min = 0.115, T_max = 0.755	k = −10→10
11464 measured reflections	l = −17→17
3139 independent reflections

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)] = 0.051	H-atom parameters constrained
wR(F²) = 0.131	w = 1/[σ²(F_o²) + (0.0662P)²] where P = (F_o² + 2F_c²)/3
S = 0.98	(Δ/σ)_max < 0.001
3139 reflections	Δρ_max = 0.73 e Å⁻³
206 parameters	Δρ_min = −0.53 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. All H atoms were positioned geometrically and rifined using a riding model, with C—H distances of 0.93 Å and methyl C—H distances 0.96 Å.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O4A	0.268 (7)	0.998 (5)	0.523 (5)	0.088 (14)	0.27 (9)
O4B	0.267 (3)	0.9909 (19)	0.474 (4)	0.127 (9)	0.73 (9)
Br01	0.16383 (8)	0.86773 (6)	0.09633 (3)	0.0673 (2)
O2	0.3544 (4)	0.3003 (3)	0.44583 (18)	0.0523 (7)
H2	0.326710	0.340164	0.495697	0.078*
O3	0.3291 (4)	0.4946 (4)	0.10287 (19)	0.0540 (7)
O1	0.3128 (4)	0.2594 (4)	0.6870 (2)	0.0571 (7)
N1	0.2236 (4)	0.5296 (4)	0.5540 (2)	0.0393 (7)
C4	0.3119 (5)	0.4231 (5)	0.3718 (3)	0.0405 (8)
C5	0.2295 (5)	0.5992 (5)	0.3830 (2)	0.0394 (8)
C2	0.3019 (5)	0.5180 (5)	0.1966 (2)	0.0425 (8)
C8	0.1872 (5)	0.6453 (5)	0.4743 (3)	0.0397 (8)
H8	0.131949	0.760763	0.478454	0.048*
C14	0.2419 (5)	0.4074 (5)	0.7224 (3)	0.0447 (9)
C6	0.1875 (5)	0.7301 (5)	0.2988 (3)	0.0431 (8)
H6	0.135573	0.844418	0.305509	0.052*
C9	0.1913 (5)	0.5563 (5)	0.6510 (2)	0.0385 (8)
C10	0.1166 (6)	0.7147 (5)	0.6772 (3)	0.0463 (9)
H10	0.082481	0.813821	0.629793	0.056*
C3	0.3453 (6)	0.3890 (5)	0.2766 (3)	0.0448 (9)
H3	0.398395	0.275763	0.267889	0.054*
C7	0.2221 (6)	0.6910 (5)	0.2087 (3)	0.0448 (9)
C11	0.0924 (6)	0.7256 (6)	0.7747 (3)	0.0557 (10)
H11	0.042377	0.832531	0.792726	0.067*
C1	0.4151 (7)	0.3224 (6)	0.0866 (3)	0.0607 (11)
H1A	0.426318	0.323287	0.018012	0.091*
H1B	0.549855	0.268133	0.115233	0.091*
H1C	0.326988	0.260190	0.115503	0.091*
C13	0.2163 (6)	0.4197 (6)	0.8193 (3)	0.0550 (10)
H13	0.248926	0.320906	0.866917	0.066*
C12	0.1421 (6)	0.5790 (6)	0.8452 (3)	0.0567 (11)
H12	0.125648	0.587391	0.910488	0.068*
C15	0.3722 (9)	0.1000 (6)	0.7530 (4)	0.0776 (15)
H15A	0.418462	0.007972	0.717331	0.116*
H15C	0.482225	0.092343	0.793208	0.116*
H15B	0.255889	0.092080	0.793013	0.116*
H4A	0.275360	1.089784	0.471441	0.116*
H4B	0.364529	0.912261	0.488679	0.116*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O4A	0.047 (15)	0.069 (14)	0.15 (3)	−0.033 (9)	0.004 (14)	−0.001 (15)
O4B	0.075 (6)	0.044 (5)	0.26 (2)	−0.022 (4)	−0.077 (9)	0.019 (8)
Br01	0.0949 (4)	0.0441 (3)	0.0399 (2)	−0.0031 (2)	−0.00083 (19)	0.00424 (17)
O2	0.0781 (18)	0.0306 (13)	0.0399 (13)	−0.0099 (12)	−0.0063 (12)	−0.0028 (11)
O3	0.0683 (17)	0.0474 (16)	0.0378 (13)	−0.0097 (13)	0.0003 (12)	−0.0090 (11)
O1	0.0797 (19)	0.0346 (15)	0.0481 (15)	−0.0107 (13)	−0.0054 (13)	−0.0028 (12)
N1	0.0445 (16)	0.0366 (16)	0.0358 (14)	−0.0127 (12)	−0.0047 (12)	−0.0056 (12)
C4	0.0441 (19)	0.0344 (19)	0.0399 (18)	−0.0101 (15)	−0.0047 (14)	−0.0048 (14)
C5	0.0435 (19)	0.0319 (18)	0.0402 (17)	−0.0106 (14)	−0.0037 (14)	−0.0039 (14)
C2	0.0438 (19)	0.044 (2)	0.0355 (17)	−0.0099 (15)	−0.0022 (14)	−0.0083 (15)
C8	0.0421 (18)	0.0339 (18)	0.0420 (18)	−0.0119 (14)	−0.0049 (14)	−0.0053 (14)
C14	0.049 (2)	0.040 (2)	0.0422 (19)	−0.0120 (16)	−0.0058 (15)	−0.0056 (16)
C6	0.053 (2)	0.0296 (18)	0.0411 (19)	−0.0071 (15)	−0.0043 (15)	−0.0058 (14)
C9	0.0384 (18)	0.042 (2)	0.0370 (17)	−0.0151 (15)	−0.0029 (13)	−0.0076 (15)
C10	0.053 (2)	0.040 (2)	0.045 (2)	−0.0126 (16)	−0.0045 (16)	−0.0102 (16)
C3	0.050 (2)	0.0319 (19)	0.047 (2)	−0.0060 (15)	−0.0048 (15)	−0.0087 (15)
C7	0.051 (2)	0.0323 (18)	0.0392 (18)	−0.0051 (15)	−0.0046 (15)	0.0040 (15)
C11	0.061 (2)	0.053 (3)	0.057 (2)	−0.0162 (19)	−0.0006 (19)	−0.022 (2)
C1	0.075 (3)	0.056 (3)	0.046 (2)	−0.011 (2)	−0.0012 (19)	−0.0194 (19)
C13	0.061 (2)	0.055 (3)	0.042 (2)	−0.0179 (19)	−0.0062 (17)	0.0029 (18)
C12	0.064 (2)	0.067 (3)	0.038 (2)	−0.018 (2)	−0.0026 (17)	−0.0144 (19)
C15	0.097 (4)	0.039 (2)	0.081 (3)	−0.013 (2)	−0.009 (3)	0.006 (2)

Geometric parameters (Å, º) top

O4A—H4A	0.96 (8)	C14—C13	1.380 (5)
O4A—H4B	0.9759	C14—C9	1.399 (5)
O4B—H4A	0.86 (7)	C6—C7	1.357 (5)
O4B—H4B	0.7704	C6—H6	0.9300
Br01—C7	1.902 (3)	C9—C10	1.374 (5)
O2—C4	1.284 (4)	C10—C11	1.387 (6)
O2—H2	0.8200	C10—H10	0.9300
O3—C2	1.361 (4)	C3—H3	0.9300
O3—C1	1.429 (5)	C11—C12	1.379 (6)
O1—C14	1.359 (5)	C11—H11	0.9300
O1—C15	1.420 (5)	C1—H1A	0.9600
N1—C8	1.306 (4)	C1—H1B	0.9600
N1—C9	1.415 (5)	C1—H1C	0.9600
C4—C3	1.412 (5)	C13—C12	1.380 (7)
C4—C5	1.436 (5)	C13—H13	0.9300
C5—C8	1.398 (5)	C12—H12	0.9300
C5—C6	1.418 (5)	C15—H15A	0.9600
C2—C3	1.369 (5)	C15—H15C	0.9600
C2—C7	1.416 (5)	C15—H15B	0.9600
C8—H8	0.9300

H4A—O4A—H4B	91.5	C11—C10—H10	120.2
H4A—O4B—H4B	116.8	C2—C3—C4	121.9 (4)
C4—O2—H2	109.5	C2—C3—H3	119.1
C2—O3—C1	117.6 (3)	C4—C3—H3	119.1
C14—O1—C15	119.2 (4)	C6—C7—C2	120.5 (3)
C8—N1—C9	127.9 (3)	C6—C7—Br01	120.6 (3)
O2—C4—C3	120.9 (3)	C2—C7—Br01	118.8 (3)
O2—C4—C5	121.3 (3)	C12—C11—C10	120.4 (4)
C3—C4—C5	117.8 (3)	C12—C11—H11	119.8
C8—C5—C6	119.1 (3)	C10—C11—H11	119.8
C8—C5—C4	121.9 (3)	O3—C1—H1A	109.5
C6—C5—C4	119.0 (3)	O3—C1—H1B	109.5
O3—C2—C3	125.0 (4)	H1A—C1—H1B	109.5
O3—C2—C7	115.3 (3)	O3—C1—H1C	109.5
C3—C2—C7	119.7 (3)	H1A—C1—H1C	109.5
N1—C8—C5	121.4 (3)	H1B—C1—H1C	109.5
N1—C8—H8	119.3	C12—C13—C14	119.8 (4)
C5—C8—H8	119.3	C12—C13—H13	120.1
O1—C14—C13	125.8 (4)	C14—C13—H13	120.1
O1—C14—C9	114.3 (3)	C11—C12—C13	120.2 (4)
C13—C14—C9	119.9 (4)	C11—C12—H12	119.9
C7—C6—C5	121.0 (3)	C13—C12—H12	119.9
C7—C6—H6	119.5	O1—C15—H15A	109.5
C5—C6—H6	119.5	O1—C15—H15C	109.5
C10—C9—C14	120.1 (3)	H15A—C15—H15C	109.5
C10—C9—N1	124.5 (3)	O1—C15—H15B	109.5
C14—C9—N1	115.4 (3)	H15A—C15—H15B	109.5
C9—C10—C11	119.6 (4)	H15C—C15—H15B	109.5
C9—C10—H10	120.2

O2—C4—C5—C8	−1.6 (5)	C8—N1—C9—C14	179.2 (3)
C3—C4—C5—C8	178.6 (3)	C14—C9—C10—C11	0.2 (6)
O2—C4—C5—C6	179.2 (3)	N1—C9—C10—C11	−179.5 (3)
C3—C4—C5—C6	−0.6 (5)	O3—C2—C3—C4	−179.6 (3)
C1—O3—C2—C3	−1.9 (6)	C7—C2—C3—C4	0.3 (6)
C1—O3—C2—C7	178.2 (4)	O2—C4—C3—C2	−179.7 (4)
C9—N1—C8—C5	179.3 (3)	C5—C4—C3—C2	0.1 (5)
C6—C5—C8—N1	−179.8 (3)	C5—C6—C7—C2	−0.3 (6)
C4—C5—C8—N1	1.0 (5)	C5—C6—C7—Br01	179.7 (3)
C15—O1—C14—C13	−1.6 (6)	O3—C2—C7—C6	179.7 (3)
C15—O1—C14—C9	179.0 (4)	C3—C2—C7—C6	−0.3 (6)
C8—C5—C6—C7	−178.6 (4)	O3—C2—C7—Br01	−0.2 (5)
C4—C5—C6—C7	0.7 (5)	C3—C2—C7—Br01	179.8 (3)
O1—C14—C9—C10	179.6 (3)	C9—C10—C11—C12	−0.2 (6)
C13—C14—C9—C10	0.2 (6)	O1—C14—C13—C12	−179.9 (4)
O1—C14—C9—N1	−0.6 (5)	C9—C14—C13—C12	−0.5 (6)
C13—C14—C9—N1	179.9 (3)	C10—C11—C12—C13	−0.1 (7)
C8—N1—C9—C10	−1.1 (6)	C14—C13—C12—C11	0.4 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.82	2.64	3.340 (4)	144
O2—H2···N1	0.82	1.84	2.581 (4)	149
O4B—H4A···O2ⁱ	0.86	2.01	2.85 (2)	166
O4B—H4B···O2ⁱⁱ	0.77	2.23	2.99 (3)	170
C8—H8···O4B	0.93	2.44	3.18 (2)	136
C10—H10···O4A	0.93	2.56	3.31 (6)	138

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

Funding information

The authors thank Ondokuz Mayıs University for research grant PYO.FEN.1904.17.013.

References

Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Köysal, Y., Bülbül, H., Dege, N., Macit, M. & Ağar, A. (2015). Crystallogr. Rep. 60, 1001–1005. 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
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany. Google Scholar

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