2,3-Dibromo-6-meth­oxy-4-[(phenethyl­amino)­methyl­idene]cyclo­hexa-2,5-dien-1-one methanol monosolvate

Ge, R.-B.; Chen, Y.-H.; Wang, F.-T.; Wang, S.-S.; Qian, S.-S.

doi:10.1107/S1600536811052895

organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o117

doi:10.1107/S1600536811052895

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2,3-Dibromo-6-methoxy-4-[(phenethylamino)methylidene]cyclohexa-2,5-dien-1-one methanol monosolvate

Rong-Bao Ge,^a Yue-Hu Chen,^a Feng-Ting Wang,^a Shuang-Shuang Wang ^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 29 November 2011; accepted 8 December 2011; online 14 December 2011)

In the title compound, C₁₆H₁₅Br₂NO₂·CH₄O, the mean planes of the substituted cyclohexa-2,5-dien-1-one and phenyl rings are almost parallel [dihedral angle = 7.84 (4)°]. The crystal packing is stabilized by N—H⋯O hydrogen bonds generating infinite [101] chains. The methanol solvent molecules are connected with the main species by O—H⋯O interactions.

Related literature

For background to bromophenols and their bioactivity, see: Liu et al. (2011 ). For related structures, see: Palmer et al. (1973 ); Li et al. (1995 ); Huang et al. (2006 ). For structural and theoretical aspects on the keto-enol equilibrium of salicylaldehyde Schiff bases, see: Chatziefthimiou et al. (2006 ).

Experimental

Crystal data

C₁₆H₁₅Br₂NO₂·CH₄O
M_r = 445.15
Monoclinic, P 2₁ /n
a = 8.752 (6) Å
b = 16.308 (10) Å
c = 13.001 (8) Å
β = 104.047 (6)°
V = 1800 (2) Å³
Z = 4
Mo Kα radiation
μ = 4.52 mm⁻¹
T = 296 K
0.25 × 0.22 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.337, T_max = 0.406
8282 measured reflections
3292 independent reflections
1674 reflections with I > 2σ(I)
R_int = 0.072

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.133
S = 1.00
3292 reflections
211 parameters
H-atom parameters constrained
Δρ_max = 0.62 e Å⁻³
Δρ_min = −0.60 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.86	1.93	2.731 (7)	154
O3—H3⋯O1ⁱⁱ	0.82	2.05	2.786 (8)	150
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x-1, y, z.

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/S1600536811052895/zq2143sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811052895/zq2143Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811052895/zq2143Isup3.cml

checkCIF report

Comment top

The 2,3-dibromo-4-hydroxy-5-methoxybenzaldehyde acts as an important precursor for the synthesis of bromophenols, which have been reported to possess a variety of biological activities (Liu et al., 2011). As an extension of our work on the 2,3-dibromo-4-hydroxy-5-methoxybenzaldehyde, the title compound was synthesized by condensing 2,3-dibromo-4-hydroxy-5-methoxybenzaldehyde with phenethylamine, and attempts to investigate its biological activities were carried out.

In the crystal structure of the title compound, C₁₆H₁₅Br₂NO₂.CH₄O, the mean planes of the substituted cyclohexa-2,5-dien-1-one and phenyl rings are almost parallel [dihedral angle = 7.84 (4)°]. Difference Fourier maps clearly showed that the N1 atom is protonated rather than the O1 atom indicating a methylidenecyclohexa-2,5-dien-1-one skeleton (Palmer et al., 1973; Huang et al., 2006; Chatziefthimiou et al., 2006). The N1 and O1 atoms are connected via a short intermolecular N—H···O hydrogen bond [N1···O1ⁱ = 2.731 (7) Å; (i) = x - 1/2, -y + 3/2, z - 1/2] generating infinite one-dimensional [101] chains (Chatziefthimiou et al., 2006). The solvent molecules of methanol are connected with the main species by O3—H3···O1ⁱⁱ interactions [O3···O1ⁱⁱ = 2.786 (8) Å; (ii) = x - 1, y, z].

Related literature top

For background to bromophenols and their bioactivity, see: Liu et al. (2011). For related structures, see: Palmer et al. (1973); Li et al. (1995); Huang et al. (2006). For structural and theoretical aspects on the keto-enol equilibrium of salicylaldehyde Schiff bases, see: Chatziefthimiou et al. (2006).

Experimental top

2,3-Dibromo-4-hydroxy-5-methoxybenzaldehyde (0.31 g) and phenethylamine (0.12 g) were dissolved in methanol (20 ml). The mixture was stirred at room temperature for 30 min to give a clear solution. Keeping the solution in air for 5 days, yellow block-shaped single crystals suitable for X-ray diffraction analysis were obtained at the bottom of the vessel.

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. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Different views of the crystal packing showing N–H···O and O–H···O hydrogen bonds (dashed lines).

2,3-Dibromo-6-methoxy-4-[(phenethylamino)methylidene]cyclohexa-2,5-dien-1- one methanol monosolvate top

Crystal data top

C₁₆H₁₅Br₂NO₂·CH₄O	Z = 4
M_r = 445.15	F(000) = 888
Monoclinic, P2₁/n	D_x = 1.643 Mg m⁻³
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 8.752 (6) Å	µ = 4.52 mm⁻¹
b = 16.308 (10) Å	T = 296 K
c = 13.001 (8) Å	Block, yellow
β = 104.047 (6)°	0.25 × 0.22 × 0.20 mm
V = 1800 (2) Å³

Data collection top

Bruker APEXII CCD diffractometer	3292 independent reflections
Radiation source: fine-focus sealed tube	1674 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.072
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −10→10
T_min = 0.337, T_max = 0.406	k = −19→14
8282 measured reflections	l = −12→15

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.051	H-atom parameters constrained
wR(F²) = 0.133	w = 1/[σ²(F_o²) + (0.0388P)² + 2.4528P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
3292 reflections	Δρ_max = 0.62 e Å⁻³
211 parameters	Δρ_min = −0.60 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0103 (10)

Crystal data top

C₁₆H₁₅Br₂NO₂·CH₄O	V = 1800 (2) Å³
M_r = 445.15	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.752 (6) Å	µ = 4.52 mm⁻¹
b = 16.308 (10) Å	T = 296 K
c = 13.001 (8) Å	0.25 × 0.22 × 0.20 mm
β = 104.047 (6)°

Data collection top

Bruker APEXII CCD diffractometer	3292 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	1674 reflections with I > 2σ(I)
T_min = 0.337, T_max = 0.406	R_int = 0.072
8282 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.133	H-atom parameters constrained
S = 1.00	Δρ_max = 0.62 e Å⁻³
3292 reflections	Δρ_min = −0.60 e Å⁻³
211 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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	0.50517 (10)	0.54245 (5)	0.37790 (6)	0.0638 (3)
Br2	0.78645 (10)	0.65471 (6)	0.52622 (6)	0.0728 (3)
O1	0.9067 (5)	0.7788 (3)	0.3957 (3)	0.0515 (13)
O2	0.8183 (6)	0.8146 (3)	0.1919 (3)	0.0544 (13)
O3	0.1533 (9)	0.8797 (5)	0.3731 (6)	0.129 (3)
H3	0.1090	0.8384	0.3873	0.193*
N1	0.3484 (6)	0.6175 (3)	0.0466 (4)	0.0429 (15)
H1	0.3848	0.6572	0.0162	0.051*
C1	0.5918 (7)	0.6306 (4)	0.3183 (5)	0.0401 (17)
C2	0.7125 (8)	0.6750 (4)	0.3797 (5)	0.0404 (17)
C3	0.7919 (8)	0.7392 (4)	0.3400 (5)	0.0373 (16)
C4	0.7342 (7)	0.7544 (4)	0.2277 (5)	0.0363 (16)
C5	0.6117 (7)	0.7126 (4)	0.1670 (5)	0.0385 (17)
H5	0.5764	0.7260	0.0956	0.046*
C6	0.5359 (7)	0.6489 (4)	0.2093 (5)	0.0347 (16)
C7	0.4111 (7)	0.6048 (4)	0.1455 (5)	0.0375 (16)
H7	0.3694	0.5623	0.1778	0.045*
C8	0.2192 (8)	0.5689 (5)	−0.0177 (5)	0.054 (2)
H8A	0.1369	0.6054	−0.0553	0.065*
H8B	0.1749	0.5342	0.0283	0.065*
C9	0.2756 (8)	0.5160 (5)	−0.0969 (6)	0.061 (2)
H9A	0.3238	0.5506	−0.1410	0.074*
H9B	0.3551	0.4781	−0.0591	0.074*
C10	0.1429 (8)	0.4687 (5)	−0.1657 (6)	0.0500 (19)
C11	0.0749 (9)	0.4913 (5)	−0.2688 (6)	0.061 (2)
H11	0.1126	0.5374	−0.2968	0.074*
C12	−0.0470 (10)	0.4476 (6)	−0.3314 (7)	0.080 (3)
H12	−0.0906	0.4644	−0.4007	0.096*
C13	−0.1036 (10)	0.3802 (6)	−0.2923 (7)	0.070 (3)
H13	−0.1845	0.3497	−0.3348	0.084*
C14	−0.0414 (9)	0.3580 (5)	−0.1913 (7)	0.067 (2)
H14	−0.0813	0.3124	−0.1636	0.080*
C15	0.0808 (8)	0.4018 (5)	−0.1279 (6)	0.055 (2)
H15	0.1215	0.3854	−0.0581	0.066*
C17	0.2388 (12)	0.8606 (7)	0.3029 (8)	0.108 (4)
H17A	0.3099	0.9047	0.2992	0.162*
H17B	0.1695	0.8520	0.2342	0.162*
H17C	0.2979	0.8115	0.3254	0.162*
C16	0.7803 (10)	0.8284 (5)	0.0801 (6)	0.075 (3)
H16A	0.7963	0.7788	0.0444	0.112*
H16B	0.8468	0.8708	0.0639	0.112*
H16C	0.6721	0.8449	0.0568	0.112*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0743 (6)	0.0668 (6)	0.0470 (5)	−0.0142 (5)	0.0082 (4)	0.0219 (4)
Br2	0.0894 (7)	0.0934 (7)	0.0260 (4)	−0.0155 (5)	−0.0043 (4)	0.0126 (4)
O1	0.059 (3)	0.059 (3)	0.031 (3)	−0.010 (3)	0.001 (2)	−0.010 (2)
O2	0.072 (3)	0.058 (3)	0.031 (3)	−0.023 (3)	0.008 (3)	−0.003 (2)
O3	0.127 (6)	0.181 (8)	0.090 (5)	−0.085 (6)	0.049 (5)	−0.052 (6)
N1	0.047 (3)	0.048 (4)	0.029 (3)	−0.004 (3)	0.001 (3)	−0.001 (3)
C1	0.039 (4)	0.047 (4)	0.033 (4)	0.008 (3)	0.008 (3)	0.006 (3)
C2	0.051 (4)	0.046 (4)	0.023 (3)	0.007 (4)	0.006 (3)	0.003 (3)
C3	0.042 (4)	0.041 (4)	0.028 (4)	0.003 (3)	0.007 (3)	−0.006 (3)
C4	0.043 (4)	0.038 (4)	0.029 (4)	−0.001 (3)	0.012 (3)	0.001 (3)
C5	0.041 (4)	0.048 (4)	0.022 (3)	0.003 (3)	−0.001 (3)	0.001 (3)
C6	0.036 (4)	0.038 (4)	0.029 (4)	0.002 (3)	0.006 (3)	0.000 (3)
C7	0.043 (4)	0.040 (4)	0.031 (4)	0.002 (3)	0.011 (3)	0.002 (3)
C8	0.051 (4)	0.067 (5)	0.042 (4)	−0.008 (4)	0.009 (4)	−0.009 (4)
C9	0.047 (5)	0.081 (6)	0.057 (5)	−0.012 (4)	0.014 (4)	−0.024 (4)
C10	0.040 (4)	0.057 (5)	0.051 (5)	0.001 (4)	0.007 (4)	−0.020 (4)
C11	0.076 (6)	0.060 (5)	0.046 (5)	−0.005 (5)	0.012 (5)	−0.008 (4)
C12	0.085 (7)	0.089 (7)	0.052 (5)	0.006 (6)	−0.008 (5)	−0.019 (5)
C13	0.060 (6)	0.070 (6)	0.073 (7)	0.001 (5)	0.004 (5)	−0.033 (5)
C14	0.062 (5)	0.062 (6)	0.080 (7)	−0.007 (4)	0.022 (5)	−0.018 (5)
C15	0.055 (5)	0.060 (5)	0.048 (5)	−0.006 (4)	0.010 (4)	−0.009 (4)
C17	0.111 (9)	0.129 (9)	0.095 (8)	−0.031 (7)	0.048 (7)	−0.020 (7)
C16	0.096 (7)	0.081 (6)	0.043 (5)	−0.031 (5)	0.010 (5)	0.012 (4)

Geometric parameters (Å, º) top

Br1—C1	1.878 (7)	C8—H8B	0.9700
Br2—C2	1.886 (6)	C9—C10	1.497 (9)
O1—C3	1.263 (7)	C9—H9A	0.9700
O2—C4	1.374 (7)	C9—H9B	0.9700
O2—C16	1.428 (8)	C10—C15	1.363 (10)
O3—C17	1.350 (10)	C10—C11	1.377 (9)
O3—H3	0.8200	C11—C12	1.373 (10)
N1—C7	1.286 (7)	C11—H11	0.9300
N1—C8	1.465 (8)	C12—C13	1.355 (11)
N1—H1	0.8600	C12—H12	0.9300
C1—C2	1.366 (9)	C13—C14	1.344 (11)
C1—C6	1.414 (8)	C13—H13	0.9300
C2—C3	1.422 (9)	C14—C15	1.380 (10)
C3—C4	1.445 (8)	C14—H14	0.9300
C4—C5	1.352 (8)	C15—H15	0.9300
C5—C6	1.414 (8)	C17—H17A	0.9600
C5—H5	0.9300	C17—H17B	0.9600
C6—C7	1.399 (8)	C17—H17C	0.9600
C7—H7	0.9300	C16—H16A	0.9600
C8—C9	1.514 (9)	C16—H16B	0.9600
C8—H8A	0.9700	C16—H16C	0.9600

C4—O2—C16	116.5 (5)	C8—C9—H9A	109.3
C17—O3—H3	109.5	C10—C9—H9B	109.3
C7—N1—C8	124.5 (6)	C8—C9—H9B	109.3
C7—N1—H1	117.7	H9A—C9—H9B	108.0
C8—N1—H1	117.7	C15—C10—C11	116.6 (7)
C2—C1—C6	120.3 (6)	C15—C10—C9	121.1 (7)
C2—C1—Br1	119.8 (5)	C11—C10—C9	122.3 (7)
C6—C1—Br1	119.9 (5)	C12—C11—C10	121.9 (8)
C1—C2—C3	123.7 (6)	C12—C11—H11	119.0
C1—C2—Br2	121.6 (5)	C10—C11—H11	119.0
C3—C2—Br2	114.7 (5)	C13—C12—C11	120.0 (8)
O1—C3—C2	124.0 (6)	C13—C12—H12	120.0
O1—C3—C4	121.7 (6)	C11—C12—H12	120.0
C2—C3—C4	114.3 (6)	C14—C13—C12	119.1 (8)
C5—C4—O2	125.2 (6)	C14—C13—H13	120.4
C5—C4—C3	122.5 (6)	C12—C13—H13	120.4
O2—C4—C3	112.3 (5)	C13—C14—C15	121.0 (8)
C4—C5—C6	121.6 (6)	C13—C14—H14	119.5
C4—C5—H5	119.2	C15—C14—H14	119.5
C6—C5—H5	119.2	C10—C15—C14	121.2 (7)
C7—C6—C5	121.3 (6)	C10—C15—H15	119.4
C7—C6—C1	121.1 (6)	C14—C15—H15	119.4
C5—C6—C1	117.6 (6)	O3—C17—H17A	109.5
N1—C7—C6	126.3 (6)	O3—C17—H17B	109.5
N1—C7—H7	116.9	H17A—C17—H17B	109.5
C6—C7—H7	116.9	O3—C17—H17C	109.5
N1—C8—C9	111.2 (6)	H17A—C17—H17C	109.5
N1—C8—H8A	109.4	H17B—C17—H17C	109.5
C9—C8—H8A	109.4	O2—C16—H16A	109.5
N1—C8—H8B	109.4	O2—C16—H16B	109.5
C9—C8—H8B	109.4	H16A—C16—H16B	109.5
H8A—C8—H8B	108.0	O2—C16—H16C	109.5
C10—C9—C8	111.5 (6)	H16A—C16—H16C	109.5
C10—C9—H9A	109.3	H16B—C16—H16C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	1.93	2.731 (7)	154
O3—H3···O1ⁱⁱ	0.82	2.05	2.786 (8)	150

Symmetry codes: (i) x−1/2, −y+3/2, z−1/2; (ii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₅Br₂NO₂·CH₄O
M_r	445.15
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	8.752 (6), 16.308 (10), 13.001 (8)
β (°)	104.047 (6)
V (Å³)	1800 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	4.52
Crystal size (mm)	0.25 × 0.22 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.337, 0.406
No. of measured, independent and observed [I > 2σ(I)] reflections	8282, 3292, 1674
R_int	0.072
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.133, 1.00
No. of reflections	3292
No. of parameters	211
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.62, −0.60

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
N1—H1···O1ⁱ	0.86	1.93	2.731 (7)	154.4
O3—H3···O1ⁱⁱ	0.82	2.05	2.786 (8)	149.8

Symmetry codes: (i) x−1/2, −y+3/2, z−1/2; (ii) x−1, y, z.

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
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Volume 68| Part 1| January 2012| Page o117

doi:10.1107/S1600536811052895

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

2,3-Di­bromo-6-meth­­oxy-4-[(phenethyl­amino)­methyl­­idene]cyclo­hexa-2,5-dien-1-one methanol monosolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2,3-Dibromo-6-methoxy-4-[(phenethylamino)methylidene]cyclohexa-2,5-dien-1-one methanol monosolvate