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

Journal logoIUCrDATA
ISSN: 2414-3146

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

CROSSMARK_Color_square_no_text.svg

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, Ow—H⋯O (w = water) hydrogen bonds link the components into centrosymmetric tetra­mers (two Schiff bases and two water mol­ecules). Weak C—H⋯Ow 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.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

As part of our ongoing studies of Schiff bases (Köysal et al., 2015[Köysal, Y., Bülbül, H., Dege, N., Macit, M. & Ağar, A. (2015). Crystallogr. Rep. 60, 1001-1005.]), we now describe the synthesis and structure of the title compound (Fig. 1[link]), which crystallizes as a monohydrate.

[Figure 1]
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[Köysal, Y., Bülbül, H., Dege, N., Macit, M. & Ağar, A. (2015). Crystallogr. Rep. 60, 1001-1005.]). An intra­molecular O—H⋯N hydrogen bond closes an S(6) ring (Table 1[link]).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[link]), Ow—H⋯O (w = water) hydrogen bonds link the components into centrosymmetric tetra­mers (two Schiff bases and two water mol­ecules). Weak C—H⋯Ow inter­actions are also observed (Table 1[link]).

[Figure 2]
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[link]. 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
Mr 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)
V3) 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[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.])
Tmin, Tmax 0.115, 0.755
No. of measured, independent and observed [I > 2σ(I)] reflections 11464, 3139, 2179
Rint 0.124
(sin θ/λ)max−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
Δρmax, Δρmin (e Å−3) 0.73, −0.53
Computer programs: X-AREA (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]), SHELXT2016 (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2016 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]), ORTEP-3 for Windows and WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Structural data


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·H2OZ = 2
Mr = 354.20F(000) = 360
Triclinic, P1Dx = 1.554 Mg m3
a = 6.922 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.498 (3) ÅCell parameters from 11116 reflections
c = 14.064 (5) Åθ = 1.5–27.6°
α = 78.30 (3)°µ = 2.73 mm1
β = 85.51 (3)°T = 293 K
γ = 69.10 (3)°Prism, yellow
V = 756.8 (6) Å30.79 × 0.39 × 0.07 mm
Data collection top
Stoe IPDS 2
diffractometer
2179 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm-1Rint = 0.124
rotation method scansθmax = 26.5°, θmin = 1.5°
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
h = 88
Tmin = 0.115, Tmax = 0.755k = 1010
11464 measured reflectionsl = 1717
3139 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.051H-atom parameters constrained
wR(F2) = 0.131 w = 1/[σ2(Fo2) + (0.0662P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max < 0.001
3139 reflectionsΔρmax = 0.73 e Å3
206 parametersΔρmin = 0.53 e Å3
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
xyzUiso*/UeqOcc. (<1)
O4A0.268 (7)0.998 (5)0.523 (5)0.088 (14)0.27 (9)
O4B0.267 (3)0.9909 (19)0.474 (4)0.127 (9)0.73 (9)
Br010.16383 (8)0.86773 (6)0.09633 (3)0.0673 (2)
O20.3544 (4)0.3003 (3)0.44583 (18)0.0523 (7)
H20.3267100.3401640.4956970.078*
O30.3291 (4)0.4946 (4)0.10287 (19)0.0540 (7)
O10.3128 (4)0.2594 (4)0.6870 (2)0.0571 (7)
N10.2236 (4)0.5296 (4)0.5540 (2)0.0393 (7)
C40.3119 (5)0.4231 (5)0.3718 (3)0.0405 (8)
C50.2295 (5)0.5992 (5)0.3830 (2)0.0394 (8)
C20.3019 (5)0.5180 (5)0.1966 (2)0.0425 (8)
C80.1872 (5)0.6453 (5)0.4743 (3)0.0397 (8)
H80.1319490.7607630.4784540.048*
C140.2419 (5)0.4074 (5)0.7224 (3)0.0447 (9)
C60.1875 (5)0.7301 (5)0.2988 (3)0.0431 (8)
H60.1355730.8444180.3055090.052*
C90.1913 (5)0.5563 (5)0.6510 (2)0.0385 (8)
C100.1166 (6)0.7147 (5)0.6772 (3)0.0463 (9)
H100.0824810.8138210.6297930.056*
C30.3453 (6)0.3890 (5)0.2766 (3)0.0448 (9)
H30.3983950.2757630.2678890.054*
C70.2221 (6)0.6910 (5)0.2087 (3)0.0448 (9)
C110.0924 (6)0.7256 (6)0.7747 (3)0.0557 (10)
H110.0423770.8325310.7927260.067*
C10.4151 (7)0.3224 (6)0.0866 (3)0.0607 (11)
H1A0.4263180.3232870.0180120.091*
H1B0.5498550.2681330.1152330.091*
H1C0.3269880.2601900.1155030.091*
C130.2163 (6)0.4197 (6)0.8193 (3)0.0550 (10)
H130.2489260.3209060.8669170.066*
C120.1421 (6)0.5790 (6)0.8452 (3)0.0567 (11)
H120.1256480.5873910.9104880.068*
C150.3722 (9)0.1000 (6)0.7530 (4)0.0776 (15)
H15A0.4184620.0079720.7173310.116*
H15C0.4822250.0923430.7932080.116*
H15B0.2558890.0920800.7930130.116*
H4A0.2753601.0897840.4714410.116*
H4B0.3645290.9122610.4886790.116*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O4A0.047 (15)0.069 (14)0.15 (3)0.033 (9)0.004 (14)0.001 (15)
O4B0.075 (6)0.044 (5)0.26 (2)0.022 (4)0.077 (9)0.019 (8)
Br010.0949 (4)0.0441 (3)0.0399 (2)0.0031 (2)0.00083 (19)0.00424 (17)
O20.0781 (18)0.0306 (13)0.0399 (13)0.0099 (12)0.0063 (12)0.0028 (11)
O30.0683 (17)0.0474 (16)0.0378 (13)0.0097 (13)0.0003 (12)0.0090 (11)
O10.0797 (19)0.0346 (15)0.0481 (15)0.0107 (13)0.0054 (13)0.0028 (12)
N10.0445 (16)0.0366 (16)0.0358 (14)0.0127 (12)0.0047 (12)0.0056 (12)
C40.0441 (19)0.0344 (19)0.0399 (18)0.0101 (15)0.0047 (14)0.0048 (14)
C50.0435 (19)0.0319 (18)0.0402 (17)0.0106 (14)0.0037 (14)0.0039 (14)
C20.0438 (19)0.044 (2)0.0355 (17)0.0099 (15)0.0022 (14)0.0083 (15)
C80.0421 (18)0.0339 (18)0.0420 (18)0.0119 (14)0.0049 (14)0.0053 (14)
C140.049 (2)0.040 (2)0.0422 (19)0.0120 (16)0.0058 (15)0.0056 (16)
C60.053 (2)0.0296 (18)0.0411 (19)0.0071 (15)0.0043 (15)0.0058 (14)
C90.0384 (18)0.042 (2)0.0370 (17)0.0151 (15)0.0029 (13)0.0076 (15)
C100.053 (2)0.040 (2)0.045 (2)0.0126 (16)0.0045 (16)0.0102 (16)
C30.050 (2)0.0319 (19)0.047 (2)0.0060 (15)0.0048 (15)0.0087 (15)
C70.051 (2)0.0323 (18)0.0392 (18)0.0051 (15)0.0046 (15)0.0040 (15)
C110.061 (2)0.053 (3)0.057 (2)0.0162 (19)0.0006 (19)0.022 (2)
C10.075 (3)0.056 (3)0.046 (2)0.011 (2)0.0012 (19)0.0194 (19)
C130.061 (2)0.055 (3)0.042 (2)0.0179 (19)0.0062 (17)0.0029 (18)
C120.064 (2)0.067 (3)0.038 (2)0.018 (2)0.0026 (17)0.0144 (19)
C150.097 (4)0.039 (2)0.081 (3)0.013 (2)0.009 (3)0.006 (2)
Geometric parameters (Å, º) top
O4A—H4A0.96 (8)C14—C131.380 (5)
O4A—H4B0.9759C14—C91.399 (5)
O4B—H4A0.86 (7)C6—C71.357 (5)
O4B—H4B0.7704C6—H60.9300
Br01—C71.902 (3)C9—C101.374 (5)
O2—C41.284 (4)C10—C111.387 (6)
O2—H20.8200C10—H100.9300
O3—C21.361 (4)C3—H30.9300
O3—C11.429 (5)C11—C121.379 (6)
O1—C141.359 (5)C11—H110.9300
O1—C151.420 (5)C1—H1A0.9600
N1—C81.306 (4)C1—H1B0.9600
N1—C91.415 (5)C1—H1C0.9600
C4—C31.412 (5)C13—C121.380 (7)
C4—C51.436 (5)C13—H130.9300
C5—C81.398 (5)C12—H120.9300
C5—C61.418 (5)C15—H15A0.9600
C2—C31.369 (5)C15—H15C0.9600
C2—C71.416 (5)C15—H15B0.9600
C8—H80.9300
H4A—O4A—H4B91.5C11—C10—H10120.2
H4A—O4B—H4B116.8C2—C3—C4121.9 (4)
C4—O2—H2109.5C2—C3—H3119.1
C2—O3—C1117.6 (3)C4—C3—H3119.1
C14—O1—C15119.2 (4)C6—C7—C2120.5 (3)
C8—N1—C9127.9 (3)C6—C7—Br01120.6 (3)
O2—C4—C3120.9 (3)C2—C7—Br01118.8 (3)
O2—C4—C5121.3 (3)C12—C11—C10120.4 (4)
C3—C4—C5117.8 (3)C12—C11—H11119.8
C8—C5—C6119.1 (3)C10—C11—H11119.8
C8—C5—C4121.9 (3)O3—C1—H1A109.5
C6—C5—C4119.0 (3)O3—C1—H1B109.5
O3—C2—C3125.0 (4)H1A—C1—H1B109.5
O3—C2—C7115.3 (3)O3—C1—H1C109.5
C3—C2—C7119.7 (3)H1A—C1—H1C109.5
N1—C8—C5121.4 (3)H1B—C1—H1C109.5
N1—C8—H8119.3C12—C13—C14119.8 (4)
C5—C8—H8119.3C12—C13—H13120.1
O1—C14—C13125.8 (4)C14—C13—H13120.1
O1—C14—C9114.3 (3)C11—C12—C13120.2 (4)
C13—C14—C9119.9 (4)C11—C12—H12119.9
C7—C6—C5121.0 (3)C13—C12—H12119.9
C7—C6—H6119.5O1—C15—H15A109.5
C5—C6—H6119.5O1—C15—H15C109.5
C10—C9—C14120.1 (3)H15A—C15—H15C109.5
C10—C9—N1124.5 (3)O1—C15—H15B109.5
C14—C9—N1115.4 (3)H15A—C15—H15B109.5
C9—C10—C11119.6 (4)H15C—C15—H15B109.5
C9—C10—H10120.2
O2—C4—C5—C81.6 (5)C8—N1—C9—C14179.2 (3)
C3—C4—C5—C8178.6 (3)C14—C9—C10—C110.2 (6)
O2—C4—C5—C6179.2 (3)N1—C9—C10—C11179.5 (3)
C3—C4—C5—C60.6 (5)O3—C2—C3—C4179.6 (3)
C1—O3—C2—C31.9 (6)C7—C2—C3—C40.3 (6)
C1—O3—C2—C7178.2 (4)O2—C4—C3—C2179.7 (4)
C9—N1—C8—C5179.3 (3)C5—C4—C3—C20.1 (5)
C6—C5—C8—N1179.8 (3)C5—C6—C7—C20.3 (6)
C4—C5—C8—N11.0 (5)C5—C6—C7—Br01179.7 (3)
C15—O1—C14—C131.6 (6)O3—C2—C7—C6179.7 (3)
C15—O1—C14—C9179.0 (4)C3—C2—C7—C60.3 (6)
C8—C5—C6—C7178.6 (4)O3—C2—C7—Br010.2 (5)
C4—C5—C6—C70.7 (5)C3—C2—C7—Br01179.8 (3)
O1—C14—C9—C10179.6 (3)C9—C10—C11—C120.2 (6)
C13—C14—C9—C100.2 (6)O1—C14—C13—C12179.9 (4)
O1—C14—C9—N10.6 (5)C9—C14—C13—C120.5 (6)
C13—C14—C9—N1179.9 (3)C10—C11—C12—C130.1 (7)
C8—N1—C9—C101.1 (6)C14—C13—C12—C110.4 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O10.822.643.340 (4)144
O2—H2···N10.821.842.581 (4)149
O4B—H4A···O2i0.862.012.85 (2)166
O4B—H4B···O2ii0.772.232.99 (3)170
C8—H8···O4B0.932.443.18 (2)136
C10—H10···O4A0.932.563.31 (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

First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationKöysal, Y., Bülbül, H., Dege, N., Macit, M. & Ağar, A. (2015). Crystallogr. Rep. 60, 1001–1005.  Google Scholar
First citationSheldrick, G. M. (2015a). Acta Cryst. A71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2015b). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationStoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.  Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoIUCrDATA
ISSN: 2414-3146
Follow IUCr Journals
Sign up for e-alerts
Follow IUCr on Twitter
Follow us on facebook
Sign up for RSS feeds

[# https x2 cm 20170801 %]