5-Bromo-2-meth-oxy-4-{[(4-meth-oxy-phen-yl)imino]-meth-yl}phenol monohydrate.

The crystal structure of the title compound, C(15)H(14)BrNO(3)·H(2)O, has a trans configuration about the central C=N double bond. An intra-molecular O-H⋯O hydrogen bond occurs in the main mol-ecule. 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 = 354.20

Orthorhombic,

a = 13.992 (4) Å

b = 7.219 (2) Å

c = 30.232 (9) Å

V = 3053.5 (15) Å3

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

Δρmax = 0.39 e Å−3

Δρmin = −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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811054742/qm2045sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811054742/qm2045Isup2.hkl

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

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

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

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 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

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.

	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)

	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)

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)

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)

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) .