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

Abstract

The crystal structure of the title compound, C₁₅H₁₄BrNO₃·H₂O, has a trans configuration about the central C=N double bond. An intra­molecular O—H⋯O hydrogen bond occurs in the main mol­ecule. The crystal packing is stabilized by strong O—H⋯O and O—H⋯N hydrogen bonds.

Related literature

For related structures, see: Shao et al. (2004 ▶); Cheng et al. (2005) ▶.

Experimental

Crystal data

• C₁₅H₁₄BrNO₃·H₂O

• M _r = 354.20

• Orthorhombic,

• a = 13.992 (4) Å

• b = 7.219 (2) Å

• c = 30.232 (9) Å

• V = 3053.5 (15) ų

• Z = 8

• Mo Kα radiation

• μ = 2.71 mm⁻¹

• T = 296 K

• 0.23 × 0.12 × 0.08 mm

Data collection

• Bruker APEXII CCD diffractometer

• Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T _min = 0.575, T _max = 0.813

• 20409 measured reflections

• 2836 independent reflections

• 1831 reflections with I > 2σ(I)

• R _int = 0.082

Refinement

• R[F ² > 2σ(F ²)] = 0.045

• wR(F ²) = 0.113

• S = 1.02

• 2836 reflections

• 201 parameters

• 3 restraints

• H atoms treated by a mixture of independent and constrained refinement

• Δρ_max = 0.39 e Å⁻³

• Δρ_min = −0.46 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Supplementary material file. DOI: 10.1107/S1600536811054742/qm2045Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.82	2.24	2.683 (4)	114
O1—H1⋯O4	0.82	1.92	2.668 (5)	152
O4—H1W⋯O1i	0.85 (3)	2.03 (4)	2.880 (5)	176 (6)
O4—H2W⋯N1ii	0.85 (4)	2.05 (4)	2.903 (5)	176 (3)

Symmetry codes: (i) ; (ii) .

supplementary crystallographic information

Comment

The 2-bromo-4-hydroxy-5-methoxybenzaldehyde can react with organic amines to form a range of Schiff bases. Schiff base compounds are well known for their wide range of biological activities and have contributed to the development of coordination chemistry related to catalysis, enzymatic reactions, magnetism and molecular architecture (Zhu et al., 2005). Here, We report one of the schiff bases which is structrually characterized to promote the development of coordination chemistry. The title compound displays a trans-configuration with respect to the C(7)=N(1) double bond. The compound crystallized in the orthorhombic system with one title compound molecule and a water molecule in the asymmetric unit. There is a π-π interaction (symmetry code: 3/2-X,1/2+Y,Z) [centroid-centroid distance =3.758 (3) Å ] There are also O(4)—H(1W)···O(1) and O(4)—H(2W)···N(1) hydrogen bonds with symmetry codes (1-x,1/2+y,1/2-z)and (-1/2+x,y,1/2-z) respectively (Figure 2 and table 1).

Experimental

The 2-bromo-4-hydroxy-5-methoxybenzaldehyde (0.1155 g) and 4-methoxyaniline (0.0616 g) were dissolved in methanol (20 mL) and reacted at room temperature for 30 mins to give a clear solution. The solution after standingin in air for 5 days gave yellow block-shaped single crystals at the bottom of the reaction vessel which were suitable for X-ray diffraction analysis.

Refinement

All H atoms were placed in geometrical positions and constrained to ride on their parent atoms with C—H distances in the range 0.93–0.96 Å, They were treated as riding atoms, with U_iso(H) = kU_eq(C), where k = 1.5 for methyl and 1.2 for all other H atoms.

Figures

Fig. 1.

The structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

Crystal data

C15H14BrNO3·H2O	Dx = 1.541 Mg m−3
Mr = 354.20	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 2836 reflections
a = 13.992 (4) Å	θ = 2.7–25.5°
b = 7.219 (2) Å	µ = 2.71 mm−1
c = 30.232 (9) Å	T = 296 K
V = 3053.5 (15) Å3	Block, yellow
Z = 8	0.23 × 0.12 × 0.08 mm
F(000) = 1440

Data collection

Bruker APEXII CCD diffractometer	2836 independent reflections
Radiation source: fine-focus sealed tube	1831 reflections with I > 2σ(I)
graphite	Rint = 0.082
φ and ω scans	θmax = 25.5°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −16→16
Tmin = 0.575, Tmax = 0.813	k = −8→8
20409 measured reflections	l = −36→33

Refinement

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0442P)2 + 3.2392P] where P = (Fo2 + 2Fc2)/3
2836 reflections	(Δ/σ)max = 0.001
201 parameters	Δρmax = 0.39 e Å−3
3 restraints	Δρmin = −0.46 e Å−3

Special details

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. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.68925 (3)	0.04514 (7)	0.438691 (15)	0.05101 (19)
C1	0.7051 (3)	0.1140 (6)	0.37837 (13)	0.0341 (10)
C2	0.6237 (3)	0.1493 (6)	0.35403 (14)	0.0377 (10)
H2	0.5640	0.1407	0.3674	0.045*
C3	0.6305 (3)	0.1969 (6)	0.31041 (14)	0.0367 (10)
C4	0.7199 (3)	0.2112 (6)	0.29032 (14)	0.0332 (10)
C5	0.8008 (3)	0.1774 (6)	0.31504 (13)	0.0324 (9)
H5	0.8604	0.1865	0.3016	0.039*
C6	0.7955 (3)	0.1300 (6)	0.35947 (13)	0.0324 (9)
C7	0.8840 (3)	0.1008 (6)	0.38482 (14)	0.0365 (10)
H7	0.8803	0.0479	0.4128	0.044*
C8	1.0489 (3)	0.1209 (6)	0.39542 (14)	0.0372 (10)
C9	1.1347 (3)	0.1063 (6)	0.37270 (14)	0.0450 (12)
H9	1.1344	0.1048	0.3419	0.054*
C10	1.2206 (3)	0.0938 (6)	0.39508 (16)	0.0469 (12)
H10	1.2773	0.0814	0.3793	0.056*
C11	1.2226 (3)	0.0996 (6)	0.44019 (15)	0.0448 (11)
C12	1.1378 (3)	0.1129 (7)	0.46330 (15)	0.0471 (12)
H12	1.1387	0.1152	0.4941	0.057*
C13	1.0520 (3)	0.1227 (6)	0.44131 (14)	0.0432 (11)
H13	0.9954	0.1307	0.4573	0.052*
C14	0.8055 (3)	0.2671 (7)	0.22380 (14)	0.0503 (12)
H14A	0.8448	0.3609	0.2371	0.075*
H14B	0.7940	0.2979	0.1934	0.075*
H14C	0.8377	0.1498	0.2255	0.075*
C15	1.3933 (3)	0.1070 (7)	0.44297 (17)	0.0636 (15)
H15A	1.4020	−0.0007	0.4248	0.095*
H15B	1.4440	0.1140	0.4643	0.095*
H15C	1.3941	0.2159	0.4247	0.095*
H1W	0.510 (4)	0.471 (4)	0.2082 (17)	0.08 (2)*
H2W	0.511 (3)	0.293 (5)	0.1846 (12)	0.068 (18)*
N1	0.9655 (2)	0.1462 (5)	0.36950 (11)	0.0368 (8)
O1	0.54833 (18)	0.2278 (5)	0.28775 (10)	0.0489 (8)
H1	0.5610	0.2520	0.2619	0.073*
O2	0.71757 (19)	0.2562 (4)	0.24658 (9)	0.0446 (8)
O3	1.3042 (2)	0.0951 (5)	0.46530 (11)	0.0578 (9)
O4	0.5312 (2)	0.3608 (6)	0.20578 (12)	0.0569 (9)

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
Br1	0.0582 (3)	0.0610 (3)	0.0338 (3)	−0.0061 (2)	0.0028 (2)	0.0022 (2)
C1	0.045 (2)	0.027 (2)	0.031 (2)	−0.0039 (18)	0.0047 (18)	−0.0021 (18)
C2	0.034 (2)	0.042 (3)	0.038 (3)	−0.0044 (19)	0.0021 (19)	−0.004 (2)
C3	0.034 (2)	0.033 (3)	0.043 (3)	0.0006 (18)	−0.0071 (19)	−0.002 (2)
C4	0.036 (2)	0.031 (2)	0.033 (2)	0.0013 (18)	−0.0013 (18)	−0.0012 (19)
C5	0.029 (2)	0.035 (2)	0.034 (2)	−0.0016 (17)	0.0002 (17)	−0.0022 (19)
C6	0.039 (2)	0.031 (2)	0.027 (2)	0.0005 (18)	−0.0050 (18)	−0.0033 (19)
C7	0.045 (2)	0.032 (3)	0.032 (2)	0.0017 (19)	−0.007 (2)	−0.0027 (19)
C8	0.036 (2)	0.037 (3)	0.038 (3)	0.0013 (18)	−0.0040 (19)	−0.001 (2)
C9	0.049 (3)	0.056 (3)	0.030 (2)	0.009 (2)	−0.002 (2)	0.003 (2)
C10	0.036 (2)	0.053 (3)	0.051 (3)	0.008 (2)	0.001 (2)	0.005 (2)
C11	0.047 (3)	0.043 (3)	0.045 (3)	0.001 (2)	−0.015 (2)	0.007 (2)
C12	0.050 (3)	0.063 (3)	0.028 (2)	−0.002 (2)	−0.005 (2)	0.001 (2)
C13	0.042 (2)	0.048 (3)	0.040 (3)	−0.003 (2)	−0.001 (2)	0.002 (2)
C14	0.049 (3)	0.070 (4)	0.032 (3)	−0.005 (3)	0.004 (2)	0.005 (2)
C15	0.046 (3)	0.064 (4)	0.081 (4)	−0.002 (2)	−0.009 (3)	0.009 (3)
N1	0.0359 (19)	0.042 (2)	0.032 (2)	0.0020 (16)	−0.0056 (15)	−0.0016 (17)
O1	0.0317 (16)	0.068 (2)	0.0469 (19)	0.0015 (14)	−0.0065 (14)	0.0111 (18)
O2	0.0406 (16)	0.060 (2)	0.0329 (17)	0.0006 (14)	−0.0063 (13)	0.0115 (15)
O3	0.0430 (18)	0.078 (3)	0.052 (2)	−0.0042 (16)	−0.0152 (16)	0.0115 (18)
O4	0.057 (2)	0.061 (3)	0.052 (2)	0.0146 (19)	−0.0209 (17)	−0.010 (2)

Geometric parameters (Å, °)

Br1—C1	1.903 (4)	C10—C11	1.365 (6)
C1—C2	1.380 (5)	C10—H10	0.9300
C1—C6	1.393 (5)	C11—O3	1.371 (5)
C2—C3	1.366 (5)	C11—C12	1.381 (6)
C2—H2	0.9300	C12—C13	1.374 (6)
C3—O1	1.356 (4)	C12—H12	0.9300
C3—C4	1.395 (5)	C13—H13	0.9300
C4—O2	1.362 (5)	C14—O2	1.413 (5)
C4—C5	1.378 (5)	C14—H14A	0.9600
C5—C6	1.388 (5)	C14—H14B	0.9600
C5—H5	0.9300	C14—H14C	0.9600
C6—C7	1.471 (5)	C15—O3	1.421 (5)
C7—N1	1.275 (5)	C15—H15A	0.9600
C7—H7	0.9300	C15—H15B	0.9600
C8—C9	1.386 (5)	C15—H15C	0.9600
C8—C13	1.388 (6)	O1—H1	0.8200
C8—N1	1.418 (5)	O4—H1W	0.855 (18)
C9—C10	1.383 (6)	O4—H2W	0.853 (18)
C9—H9	0.9300
C2—C1—C6	121.0 (4)	C11—C10—H10	119.8
C2—C1—Br1	117.6 (3)	C9—C10—H10	119.8
C6—C1—Br1	121.4 (3)	C10—C11—O3	124.7 (4)
C3—C2—C1	120.3 (4)	C10—C11—C12	119.3 (4)
C3—C2—H2	119.9	O3—C11—C12	115.9 (4)
C1—C2—H2	119.9	C13—C12—C11	120.7 (4)
O1—C3—C2	118.0 (4)	C13—C12—H12	119.7
O1—C3—C4	121.9 (4)	C11—C12—H12	119.7
C2—C3—C4	120.1 (4)	C12—C13—C8	120.6 (4)
O2—C4—C5	126.1 (4)	C12—C13—H13	119.7
O2—C4—C3	114.8 (3)	C8—C13—H13	119.7
C5—C4—C3	119.2 (4)	O2—C14—H14A	109.5
C4—C5—C6	121.7 (4)	O2—C14—H14B	109.5
C4—C5—H5	119.2	H14A—C14—H14B	109.5
C6—C5—H5	119.2	O2—C14—H14C	109.5
C5—C6—C1	117.8 (3)	H14A—C14—H14C	109.5
C5—C6—C7	119.6 (4)	H14B—C14—H14C	109.5
C1—C6—C7	122.6 (4)	O3—C15—H15A	109.5
N1—C7—C6	121.8 (4)	O3—C15—H15B	109.5
N1—C7—H7	119.1	H15A—C15—H15B	109.5
C6—C7—H7	119.1	O3—C15—H15C	109.5
C9—C8—C13	118.0 (4)	H15A—C15—H15C	109.5
C9—C8—N1	116.6 (4)	H15B—C15—H15C	109.5
C13—C8—N1	125.2 (4)	C7—N1—C8	120.2 (4)
C10—C9—C8	121.0 (4)	C3—O1—H1	109.5
C10—C9—H9	119.5	C4—O2—C14	117.7 (3)
C8—C9—H9	119.5	C11—O3—C15	117.8 (4)
C11—C10—C9	120.3 (4)	H1W—O4—H2W	119 (3)
C6—C1—C2—C3	1.4 (6)	C13—C8—C9—C10	0.0 (7)
Br1—C1—C2—C3	−179.1 (3)	N1—C8—C9—C10	175.6 (4)
C1—C2—C3—O1	179.1 (4)	C8—C9—C10—C11	−1.4 (7)
C1—C2—C3—C4	−0.4 (6)	C9—C10—C11—O3	−177.5 (4)
O1—C3—C4—O2	−0.7 (6)	C9—C10—C11—C12	1.8 (7)
C2—C3—C4—O2	178.8 (4)	C10—C11—C12—C13	−0.9 (7)
O1—C3—C4—C5	−179.7 (4)	O3—C11—C12—C13	178.5 (4)
C2—C3—C4—C5	−0.2 (6)	C11—C12—C13—C8	−0.5 (7)
O2—C4—C5—C6	−179.1 (4)	C9—C8—C13—C12	0.9 (7)
C3—C4—C5—C6	−0.2 (6)	N1—C8—C13—C12	−174.3 (4)
C4—C5—C6—C1	1.2 (6)	C6—C7—N1—C8	178.2 (4)
C4—C5—C6—C7	−178.1 (4)	C9—C8—N1—C7	156.8 (4)
C2—C1—C6—C5	−1.8 (6)	C13—C8—N1—C7	−28.0 (7)
Br1—C1—C6—C5	178.8 (3)	C5—C4—O2—C14	1.0 (6)
C2—C1—C6—C7	177.5 (4)	C3—C4—O2—C14	−178.0 (4)
Br1—C1—C6—C7	−2.0 (6)	C10—C11—O3—C15	7.8 (7)
C5—C6—C7—N1	11.5 (6)	C12—C11—O3—C15	−171.6 (4)
C1—C6—C7—N1	−167.7 (4)

Hydrogen-bond geometry (Å, °)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	2.24	2.683 (4)	114
O1—H1···O4	0.82	1.92	2.668 (5)	152
O4—H1W···O1i	0.85 (3)	2.03 (4)	2.880 (5)	176 (6)
O4—H2W···N1ii	0.85 (4)	2.05 (4)	2.903 (5)	176 (3)

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