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

Mao, C.-G.; Wang, S.-S.; Su, D.-C.; Qian, S.-S.

doi:10.1107/S1600536811054742

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o249

doi:10.1107/S1600536811054742

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

Cheng-Gong Mao,^a Shuang-Shuang Wang,^a Deng-Cheng Su ^a and Shao-Song Qian ^a ^*

^aSchool of Life Sciences, ShanDong University of Technology, ZiBo 255049, People's Republic of China
^*Correspondence e-mail: njuqss@yahoo.com.cn

(Received 16 December 2011; accepted 20 December 2011; online 7 January 2012)

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, P b c a
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[F² > 2σ(F²)] = 0.045
wR(F²) = 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

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) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811054742/qm2045sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811054742/qm2045Isup3.cml

checkCIF report

Comment top

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).

Related literature top

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

Experimental top

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.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

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

Crystal data top

C₁₅H₁₄BrNO₃·H₂O	D_x = 1.541 Mg m⁻³
M_r = 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 top

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

Refinement top

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 = 1.02	w = 1/[σ²(F_o²) + (0.0442P)² + 3.2392P] where P = (F_o² + 2F_c²)/3
2836 reflections	(Δ/σ)_max = 0.001
201 parameters	Δρ_max = 0.39 e Å⁻³
3 restraints	Δρ_min = −0.46 e Å⁻³

Crystal data top

C₁₅H₁₄BrNO₃·H₂O	V = 3053.5 (15) Å³
M_r = 354.20	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 13.992 (4) Å	µ = 2.71 mm⁻¹
b = 7.219 (2) Å	T = 296 K
c = 30.232 (9) Å	0.23 × 0.12 × 0.08 mm

Data collection top

Bruker APEXII CCD diffractometer	2836 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	1831 reflections with I > 2σ(I)
T_min = 0.575, T_max = 0.813	R_int = 0.082
20409 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	3 restraints
wR(F²) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.39 e Å⁻³
2836 reflections	Δρ_min = −0.46 e Å⁻³
201 parameters

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. 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 (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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, º) top

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, º) top

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.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄BrNO₃·H₂O
M_r	354.20
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	13.992 (4), 7.219 (2), 30.232 (9)
V (Å³)	3053.5 (15)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	2.71
Crystal size (mm)	0.23 × 0.12 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.575, 0.813
No. of measured, independent and observed [I > 2σ(I)] reflections	20409, 2836, 1831
R_int	0.082
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.113, 1.02
No. of reflections	2836
No. of parameters	201
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.46

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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.

Acknowledgements

This project was sponsored by the ShanDong Province Science & Technology Innovation Foundation (People's Republic of China).

References

Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cheng, K., You, Z.-L., Li, Y.-G. & Zhu, H.-L. (2005). Acta Cryst. E61, o1137–o1138. Web of Science CrossRef IUCr Journals Google Scholar
Shao, S.-C., You, Z.-L., Fan, S.-H., Tang, L.-L., Xiong, Z.-D. & Zhu, H.-L. (2004). Acta Cryst. E60, o2183–o2184. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar