1,6-Di-bromo-naphthalen-2-ol methanol monosolvate.

The naphthol-containing mol-ecule of the title compound, C10H6Br2O·CH3OH, crystallized as a methanol monosolvate and is planar to within 0.069 (1) Å for all non-H atoms. In the crystal, mol-ecules are linked by two pairs of O-H⋯O hydrogen bonds, involving the methanol mol-ecule, forming dimer-like arrangements. The crystal structure is further stabilized by π-π stacking [centroid-centroid distance = 3.676 (2) Å] and Br⋯Br inter-actions [3.480 (4) and 3.786 (1) Å], forming a three-dimensional structure.

Related literature

For information on applications of 1,6-di­bromo-2-napthol, see: Costa et al. (2012 ▶); Takeuchi et al. (2000 ▶); Kalra & Kumar (2005 ▶). For related structures, see: Rozycka-Sokolowska & Marciniak (2009 ▶). For halogen–halogen inter­actions, see: Zordan & Brammer (2006 ▶); Schlueter et al. (2012 ▶); Desiraju & Parthasarathy (1989 ▶).

Experimental

Crystal data

C10H6Br2O·CH4O

M = 334.01

Monoclinic,

a = 3.9971 (4) Å

b = 12.4705 (12) Å

c = 22.462 (2) Å

β = 92.442 (1)°

V = 1118.62 (19) Å3

Z = 4

Mo Kα radiation

μ = 7.22 mm−1

T = 100 K

0.26 × 0.11 × 0.01 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2011 ▶) T min = 0.521, T max = 0.746

12658 measured reflections

2690 independent reflections

2082 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.074

S = 1.02

2690 reflections

138 parameters

H-atom parameters constrained

Δρmax = 1.31 e Å−3

Δρmin = −0.60 e Å−3

Data collection: APEX2 (Bruker, 2011 ▶); cell refinement: SAINT (Bruker, 2011 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: CrystalMaker (CrystalMaker Software, 2009 ▶); software used to prepare material for publication: enCIFer (Allen et al., 2004 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813016371/su2599sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813016371/su2599Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813016371/su2599Isup3.cml

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

C10H6Br2O·CH4O	F(000) = 648
Mr = 334.01	Dx = 1.983 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yn	Cell parameters from 125 reflections
a = 3.9971 (4) Å	θ = 5.5–28.9°
b = 12.4705 (12) Å	µ = 7.22 mm−1
c = 22.462 (2) Å	T = 100 K
β = 92.442 (1)°	Plate, colourless
V = 1118.62 (19) Å3	0.26 × 0.11 × 0.01 mm
Z = 4

Bruker APEXII CCD diffractometer	2690 independent reflections
Radiation source: fine-focus sealed tube	2082 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.057
Detector resolution: 8.3333 pixels mm-1	θmax = 28.5°, θmin = 1.8°
ω and φ scans	h = −5→5
Absorption correction: multi-scan (SADABS; Bruker, 2011)	k = −16→15
Tmin = 0.521, Tmax = 0.746	l = −29→29
12658 measured reflections

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.074	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0264P)2 + 1.7105P] where P = (Fo2 + 2Fc2)/3
2690 reflections	(Δ/σ)max = 0.002
138 parameters	Δρmax = 1.31 e Å−3
0 restraints	Δρmin = −0.60 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.11971 (11)	0.48530 (3)	0.57493 (2)	0.0238 (1)
Br2	0.46378 (10)	0.69738 (3)	0.87432 (2)	0.0191 (1)
O1	0.8338 (7)	0.50830 (19)	0.92461 (11)	0.0218 (9)
C1	0.2711 (9)	0.5134 (3)	0.65501 (16)	0.0160 (11)
C2	0.4589 (9)	0.4385 (3)	0.68511 (17)	0.0181 (11)
C3	0.5579 (9)	0.4567 (3)	0.74594 (17)	0.0154 (11)
C4	0.4629 (9)	0.5538 (3)	0.77388 (16)	0.0158 (10)
C5	0.5664 (9)	0.5675 (3)	0.83471 (17)	0.0155 (10)
C6	0.7448 (9)	0.4917 (3)	0.86645 (17)	0.0176 (11)
C7	0.1771 (9)	0.6095 (3)	0.68189 (17)	0.0185 (11)
C8	0.2723 (9)	0.6286 (3)	0.74024 (17)	0.0178 (11)
C9	0.7470 (9)	0.3789 (3)	0.77869 (17)	0.0175 (11)
C10	0.8383 (9)	0.3942 (3)	0.83702 (17)	0.0197 (11)
O2	0.1551 (8)	0.3491 (2)	0.97853 (13)	0.0287 (9)
C11	−0.0041 (11)	0.2471 (3)	0.98332 (19)	0.0286 (14)
H1	0.94170	0.45510	0.93800	0.0330*
H2A	0.52360	0.37460	0.66570	0.0220*
H7	0.04810	0.66100	0.65980	0.0220*
H8	0.20790	0.69390	0.75830	0.0210*
H9	0.81130	0.31480	0.75950	0.0210*
H10	0.96350	0.34080	0.85830	0.0240*
H2	0.17580	0.37740	1.01240	0.0430*
H11A	0.11630	0.20400	1.01380	0.0430*
H11B	−0.00170	0.20990	0.94490	0.0430*
H11C	−0.23620	0.25730	0.99460	0.0430*

	U11	U22	U33	U12	U13	U23
Br1	0.0299 (2)	0.0256 (2)	0.0156 (2)	−0.0058 (2)	−0.0031 (2)	0.0001 (2)
Br2	0.0230 (2)	0.0152 (2)	0.0191 (2)	0.0037 (2)	−0.0005 (2)	−0.0024 (2)
O1	0.0330 (17)	0.0166 (13)	0.0152 (14)	0.0041 (11)	−0.0052 (12)	0.0022 (11)
C1	0.0176 (19)	0.0182 (18)	0.0122 (18)	−0.0078 (15)	0.0007 (15)	−0.0009 (14)
C2	0.019 (2)	0.0136 (17)	0.022 (2)	−0.0052 (15)	0.0031 (16)	−0.0035 (15)
C3	0.0129 (18)	0.0165 (17)	0.017 (2)	−0.0035 (14)	0.0041 (15)	0.0011 (14)
C4	0.0148 (18)	0.0159 (17)	0.0168 (19)	−0.0043 (14)	0.0028 (15)	−0.0015 (15)
C5	0.0137 (18)	0.0121 (16)	0.021 (2)	0.0005 (14)	0.0032 (15)	−0.0023 (14)
C6	0.0181 (19)	0.0160 (17)	0.0187 (19)	−0.0041 (15)	−0.0001 (15)	0.0011 (15)
C7	0.0165 (19)	0.0158 (18)	0.023 (2)	−0.0040 (15)	0.0002 (16)	0.0050 (15)
C8	0.018 (2)	0.0156 (17)	0.020 (2)	−0.0036 (14)	0.0039 (16)	−0.0027 (15)
C9	0.0171 (19)	0.0135 (17)	0.022 (2)	0.0002 (14)	0.0029 (16)	−0.0008 (15)
C10	0.0159 (19)	0.024 (2)	0.019 (2)	−0.0074 (15)	−0.0001 (16)	−0.0015 (16)
O2	0.0408 (18)	0.0207 (14)	0.0239 (16)	0.0050 (13)	−0.0063 (14)	−0.0016 (12)
C11	0.034 (3)	0.025 (2)	0.027 (2)	0.0026 (18)	0.0030 (19)	0.0009 (18)

Br1—C1	1.906 (4)	C5—C6	1.366 (5)
Br2—C5	1.901 (4)	C6—C10	1.441 (5)
O1—C6	1.355 (5)	C7—C8	1.370 (5)
O1—H1	0.8400	C9—C10	1.359 (5)
O2—C11	1.428 (5)	C2—H2A	0.9500
O2—H2	0.8400	C7—H7	0.9500
C1—C2	1.360 (5)	C8—H8	0.9500
C1—C7	1.400 (5)	C9—H9	0.9500
C2—C3	1.424 (5)	C10—H10	0.9500
C3—C9	1.417 (5)	C11—H11A	0.9800
C3—C4	1.423 (5)	C11—H11B	0.9800
C4—C5	1.421 (5)	C11—H11C	0.9800
C4—C8	1.404 (5)
C6—O1—H1	110.00	C4—C8—C7	121.4 (3)
C11—O2—H2	109.00	C3—C9—C10	121.3 (3)
Br1—C1—C7	119.0 (3)	C6—C10—C9	119.8 (3)
Br1—C1—C2	119.3 (3)	C3—C2—H2A	120.00
C2—C1—C7	121.7 (3)	C1—C2—H2A	120.00
C1—C2—C3	119.5 (3)	C1—C7—H7	120.00
C2—C3—C4	119.4 (3)	C8—C7—H7	120.00
C2—C3—C9	120.6 (3)	C7—C8—H8	119.00
C4—C3—C9	120.0 (3)	C4—C8—H8	119.00
C3—C4—C8	118.5 (3)	C3—C9—H9	119.00
C3—C4—C5	117.0 (3)	C10—C9—H9	119.00
C5—C4—C8	124.5 (3)	C6—C10—H10	120.00
Br2—C5—C6	117.6 (3)	C9—C10—H10	120.00
C4—C5—C6	122.9 (3)	O2—C11—H11A	109.00
Br2—C5—C4	119.5 (3)	O2—C11—H11B	110.00
O1—C6—C10	120.6 (3)	O2—C11—H11C	109.00
C5—C6—C10	119.0 (3)	H11A—C11—H11B	109.00
O1—C6—C5	120.5 (3)	H11A—C11—H11C	109.00
C1—C7—C8	119.5 (3)	H11B—C11—H11C	110.00
Br1—C1—C2—C3	−176.7 (3)	C3—C4—C5—C6	−1.0 (5)
C7—C1—C2—C3	1.3 (6)	C8—C4—C5—Br2	−3.1 (5)
Br1—C1—C7—C8	177.2 (3)	C8—C4—C5—C6	178.3 (4)
C2—C1—C7—C8	−0.8 (6)	C3—C4—C8—C7	0.2 (5)
C1—C2—C3—C4	−1.0 (5)	C5—C4—C8—C7	−179.1 (4)
C1—C2—C3—C9	178.6 (3)	Br2—C5—C6—O1	2.1 (5)
C2—C3—C4—C5	179.6 (3)	Br2—C5—C6—C10	−177.5 (3)
C2—C3—C4—C8	0.2 (5)	C4—C5—C6—O1	−179.2 (3)
C9—C3—C4—C5	0.1 (5)	C4—C5—C6—C10	1.2 (6)
C9—C3—C4—C8	−179.3 (3)	O1—C6—C10—C9	−180.0 (3)
C2—C3—C9—C10	−178.8 (4)	C5—C6—C10—C9	−0.3 (5)
C4—C3—C9—C10	0.7 (6)	C1—C7—C8—C4	0.0 (6)
C3—C4—C5—Br2	177.6 (3)	C3—C9—C10—C6	−0.6 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.84	1.80	2.632 (4)	171
O2—H2···O1ii	0.84	2.01	2.809 (4)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.84	1.80	2.632 (4)	171
O2—H2⋯O1ii	0.84	2.01	2.809 (4)	159

Symmetry codes: (i) ; (ii) .