2,3-Dibromo-6-meth-oxy-4-[(phenethyl-amino)-methyl-idene]cyclo-hexa-2,5-dien-1-one methanol monosolvate.

In the title compound, C(16)H(15)Br(2)NO(2)·CH(4)O, the mean planes of the substituted cyclo-hexa-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 mol-ecules are connected with the main species by O-H⋯O inter-actions.

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 = 445.15

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.133

S = 1.00

3292 reflections

211 parameters

H-atom parameters constrained

Δρmax = 0.62 e Å−3

Δρmin = −0.60 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/S1600536811052895/zq2143sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811052895/zq2143Isup3.cml

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

C16H15Br2NO2·CH4O	Z = 4
Mr = 445.15	F(000) = 888
Monoclinic, P21/n	Dx = 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

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

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(Fo2) + (0.0388P)2 + 2.4528P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.001
3292 reflections	Δρmax = 0.62 e Å−3
211 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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

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.

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) ; (ii) .