organic compounds
(E)-4-Bromo-5-methoxy-2-{[(2-methoxyphenyl)imino]methyl}phenol monohydrate
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
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 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.
CCDC reference: 1588757
Structure description
As part of our ongoing studies of et al., 2015), we now describe the synthesis and structure of the title compound (Fig. 1), which crystallizes as a monohydrate.
(KöysalThe 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).
In the crystal (Fig. 2), Ow—H⋯O (w = water) hydrogen bonds link the components into centrosymmetric tetramers (two and two water molecules). Weak C—H⋯Ow interactions are also observed (Table 1).
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 . The O atom of the water molecule of crystallization is disordered over two adjacent sites in a 0.73 (9):0.27 (9) ratio.
details are summarized in Table 2
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Structural data
CCDC reference: 1588757
https://doi.org/10.1107/S2414314617017308/hb4187sup1.cif
contains datablocks hakan12, I. DOI: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
Data collection: X-AREA (Stoe & Cie, 2002); cell
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).C15H14BrNO3·H2O | Z = 2 |
Mr = 354.20 | F(000) = 360 |
Triclinic, P1 | Dx = 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 |
Stoe IPDS 2 diffractometer | 2179 reflections with I > 2σ(I) |
Detector resolution: 6.67 pixels mm-1 | Rint = 0.124 |
rotation method scans | θmax = 26.5°, θmin = 1.5° |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | h = −8→8 |
Tmin = 0.115, Tmax = 0.755 | k = −10→10 |
11464 measured reflections | l = −17→17 |
3139 independent reflections |
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(Fo2) + (0.0662P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.98 | (Δ/σ)max < 0.001 |
3139 reflections | Δρmax = 0.73 e Å−3 |
206 parameters | Δρmin = −0.53 e Å−3 |
0 restraints |
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. |
x | y | z | Uiso*/Ueq | 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* |
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) |
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) |
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
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