1,4-Dibromo­naphthalene-2,3-diol

Gao, Q.; Zhu, Y.

doi:10.1107/S1600536811026997

organic compounds

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Volume 67| Part 8| August 2011| Page o2009

doi:10.1107/S1600536811026997

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1,4-Dibromonaphthalene-2,3-diol

Qinghe Gao ^a ^* and Yanping Zhu ^a

^aKey Laboratory of Pesticide and Chemical Biology of Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China
^*Correspondence e-mail: gao_qinghe@163.com

(Received 1 July 2011; accepted 6 July 2011; online 13 July 2011)

In the title compound (r.m.s. deviation for the non-H atoms = 0.020 Å), C₁₀H₆Br₂O₂, an intramolecular O—H⋯O hydrogen bond generates an S(6) ring. In the crystal, the same H atom also forms an intermolecular O—H⋯O hydrogen bond, generating a C(2) chain propagating in [100]. The other O—H hydrogen forms a weak O—H⋯π interaction, and short Br⋯Br contacts [3.5972 (9) Å] also occur.

Related literature

For the synthesis, see: Lai et al. (1993 ). For a related structure, see: Ahn et al. (2009 ).

Experimental

Crystal data

C₁₀H₆Br₂O₂
M_r = 317.96
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.0928 (9) Å
b = 11.932 (2) Å
c = 15.779 (3) Å
V = 958.9 (3) Å³
Z = 4
Mo Kα radiation
μ = 8.42 mm⁻¹
T = 298 K
0.16 × 0.12 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.356, T_max = 0.486
6339 measured reflections
2363 independent reflections
2156 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.068
S = 1.00
2363 reflections
133 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.40 e Å⁻³
Absolute structure: Flack (1983 ), 899 Friedel pairs
Flack parameter: 0.034 (15)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯Cg1ⁱ	0.82 (1)	2.94 (5)	3.441 (3)	122 (4)
O2—H2A⋯O2ⁱⁱ	0.81 (1)	2.26 (2)	3.038 (3)	161 (4)
O2—H2A⋯O1	0.81 (1)	2.24 (4)	2.653 (4)	112 (4)
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811026997/hb5940sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811026997/hb5940Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811026997/hb5940Isup3.cml

checkCIF report

Related literature top

For the synthesis, see: Lai et al. (1993). For a related structure, see: Ahn et al. (2009).

Experimental top

The title compound was synthesized according to the literature method (Lai et al., 1993). Crystals of (I) were grown by slow evaporation of a chloroform-methanol (5:1) solution at room temperature.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

Fig. 1. A view of (I), with displacement ellipsoids drawn at the 30% probability level.

1,4-Dibromonaphthalene-2,3-diol top

Crystal data top

C₁₀H₆Br₂O₂	F(000) = 608
M_r = 317.96	D_x = 2.203 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3125 reflections
a = 5.0928 (9) Å	θ = 2.6–27.3°
b = 11.932 (2) Å	µ = 8.42 mm⁻¹
c = 15.779 (3) Å	T = 298 K
V = 958.9 (3) Å³	Block, colorless
Z = 4	0.16 × 0.12 × 0.10 mm

Data collection top

Bruker SMART APEX CCD diffractometer	2363 independent reflections
Radiation source: fine-focus sealed tube	2156 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
phi and ω scans	θ_max = 28.3°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −6→5
T_min = 0.356, T_max = 0.486	k = −15→15
6339 measured reflections	l = −18→21

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)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.068	w = 1/[σ²(F_o²) + (0.0277P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
2363 reflections	Δρ_max = 0.37 e Å⁻³
133 parameters	Δρ_min = −0.40 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 899 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.034 (15)

Crystal data top

C₁₀H₆Br₂O₂	V = 958.9 (3) Å³
M_r = 317.96	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 5.0928 (9) Å	µ = 8.42 mm⁻¹
b = 11.932 (2) Å	T = 298 K
c = 15.779 (3) Å	0.16 × 0.12 × 0.10 mm

Data collection top

Bruker SMART APEX CCD diffractometer	2363 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2156 reflections with I > 2σ(I)
T_min = 0.356, T_max = 0.486	R_int = 0.039
6339 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.068	Δρ_max = 0.37 e Å⁻³
S = 1.00	Δρ_min = −0.40 e Å⁻³
2363 reflections	Absolute structure: Flack (1983), 899 Friedel pairs
133 parameters	Absolute structure parameter: 0.034 (15)
2 restraints

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	−0.18029 (8)	0.17357 (3)	0.16514 (2)	0.04109 (12)
Br2	0.61683 (7)	0.45789 (3)	0.40915 (2)	0.04028 (12)
C1	0.4056 (7)	0.3970 (3)	0.24593 (19)	0.0273 (7)
C2	0.5849 (7)	0.4724 (3)	0.2089 (2)	0.0331 (7)
H2	0.7024	0.5113	0.2431	0.040*
C3	0.5879 (8)	0.4891 (3)	0.1222 (2)	0.0409 (9)
H3	0.7077	0.5386	0.0982	0.049*
C4	0.4101 (8)	0.4313 (3)	0.0709 (2)	0.0423 (9)
H4	0.4103	0.4444	0.0128	0.051*
C5	0.2376 (8)	0.3569 (3)	0.1037 (2)	0.0360 (8)
H5	0.1239	0.3183	0.0679	0.043*
C6	0.2291 (7)	0.3372 (3)	0.19325 (18)	0.0285 (7)
C7	0.0531 (7)	0.2609 (3)	0.23054 (18)	0.0289 (7)
C8	0.0467 (7)	0.2438 (3)	0.31682 (19)	0.0291 (7)
C9	0.2215 (7)	0.3043 (3)	0.37007 (19)	0.0285 (7)
C10	0.3945 (7)	0.3778 (3)	0.33519 (19)	0.0267 (6)
O1	−0.1160 (6)	0.1729 (2)	0.35854 (16)	0.0424 (6)
H1A	−0.251 (5)	0.151 (4)	0.336 (3)	0.064*
O2	0.2141 (6)	0.2872 (2)	0.45569 (15)	0.0389 (6)
H2A	0.072 (5)	0.261 (4)	0.468 (3)	0.058*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0417 (2)	0.0386 (2)	0.04299 (19)	−0.00633 (18)	−0.00583 (16)	−0.00902 (16)
Br2	0.0427 (2)	0.0432 (2)	0.03491 (16)	−0.00489 (18)	−0.00972 (15)	−0.00380 (15)
C1	0.0291 (18)	0.0237 (15)	0.0290 (14)	0.0050 (14)	0.0019 (14)	−0.0014 (12)
C2	0.0373 (19)	0.0308 (18)	0.0311 (14)	−0.0022 (16)	0.0035 (14)	−0.0004 (14)
C3	0.046 (2)	0.041 (2)	0.0359 (16)	−0.0081 (18)	0.0107 (16)	0.0062 (16)
C4	0.051 (2)	0.048 (2)	0.0274 (15)	0.002 (2)	0.0016 (15)	0.0048 (15)
C5	0.042 (2)	0.0394 (19)	0.0269 (15)	0.0025 (16)	−0.0019 (14)	−0.0007 (14)
C6	0.0333 (19)	0.0274 (16)	0.0248 (13)	0.0058 (15)	0.0004 (12)	−0.0010 (13)
C7	0.0299 (18)	0.0271 (17)	0.0296 (15)	−0.0002 (14)	−0.0038 (13)	−0.0058 (13)
C8	0.0304 (18)	0.0238 (16)	0.0332 (15)	0.0018 (14)	0.0028 (13)	0.0027 (13)
C9	0.0329 (19)	0.0290 (17)	0.0235 (13)	0.0054 (14)	−0.0009 (13)	0.0020 (12)
C10	0.0298 (16)	0.0245 (15)	0.0256 (13)	−0.0004 (14)	−0.0059 (14)	−0.0037 (12)
O1	0.0440 (16)	0.0422 (15)	0.0408 (13)	−0.0125 (14)	0.0013 (12)	0.0070 (11)
O2	0.0422 (16)	0.0486 (15)	0.0258 (10)	−0.0055 (13)	0.0010 (10)	0.0066 (11)

Geometric parameters (Å, º) top

Br1—C7	1.888 (3)	C5—C6	1.434 (4)
Br2—C10	1.886 (3)	C5—H5	0.9300
C1—C2	1.409 (5)	C6—C7	1.407 (5)
C1—C6	1.417 (5)	C7—C8	1.377 (4)
C1—C10	1.428 (4)	C8—O1	1.355 (4)
C2—C3	1.383 (4)	C8—C9	1.421 (5)
C2—H2	0.9300	C9—C10	1.359 (5)
C3—C4	1.397 (5)	C9—O2	1.367 (4)
C3—H3	0.9300	O1—H1A	0.819 (10)
C4—C5	1.352 (5)	O2—H2A	0.810 (10)
C4—H4	0.9300

C2—C1—C6	119.3 (3)	C7—C6—C5	122.5 (3)
C2—C1—C10	122.5 (3)	C1—C6—C5	118.5 (3)
C6—C1—C10	118.2 (3)	C8—C7—C6	121.6 (3)
C3—C2—C1	120.6 (3)	C8—C7—Br1	116.4 (3)
C3—C2—H2	119.7	C6—C7—Br1	122.0 (2)
C1—C2—H2	119.7	O1—C8—C7	126.0 (3)
C2—C3—C4	119.7 (3)	O1—C8—C9	114.4 (3)
C2—C3—H3	120.1	C7—C8—C9	119.6 (3)
C4—C3—H3	120.1	C10—C9—O2	121.0 (3)
C5—C4—C3	121.6 (3)	C10—C9—C8	119.6 (3)
C5—C4—H4	119.2	O2—C9—C8	119.4 (3)
C3—C4—H4	119.2	C9—C10—C1	121.9 (3)
C4—C5—C6	120.3 (3)	C9—C10—Br2	117.7 (2)
C4—C5—H5	119.9	C1—C10—Br2	120.4 (2)
C6—C5—H5	119.9	C8—O1—H1A	120 (3)
C7—C6—C1	119.0 (3)	C9—O2—H2A	108 (3)

C6—C1—C2—C3	0.7 (5)	Br1—C7—C8—O1	−2.0 (5)
C10—C1—C2—C3	−179.5 (3)	C6—C7—C8—C9	0.0 (5)
C1—C2—C3—C4	0.5 (6)	Br1—C7—C8—C9	178.4 (2)
C2—C3—C4—C5	−1.6 (6)	O1—C8—C9—C10	179.8 (3)
C3—C4—C5—C6	1.4 (6)	C7—C8—C9—C10	−0.5 (5)
C2—C1—C6—C7	179.1 (3)	O1—C8—C9—O2	0.3 (5)
C10—C1—C6—C7	−0.7 (5)	C7—C8—C9—O2	179.9 (3)
C2—C1—C6—C5	−0.8 (5)	O2—C9—C10—C1	180.0 (3)
C10—C1—C6—C5	179.4 (3)	C8—C9—C10—C1	0.4 (5)
C4—C5—C6—C7	179.8 (3)	O2—C9—C10—Br2	−1.7 (4)
C4—C5—C6—C1	−0.2 (5)	C8—C9—C10—Br2	178.8 (2)
C1—C6—C7—C8	0.6 (5)	C2—C1—C10—C9	−179.6 (3)
C5—C6—C7—C8	−179.5 (3)	C6—C1—C10—C9	0.2 (5)
C1—C6—C7—Br1	−177.7 (2)	C2—C1—C10—Br2	2.0 (4)
C5—C6—C7—Br1	2.2 (5)	C6—C1—C10—Br2	−178.1 (2)
C6—C7—C8—O1	179.6 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···Cg1ⁱ	0.82 (1)	2.94 (5)	3.441 (3)	122 (4)
O2—H2A···O2ⁱⁱ	0.81 (1)	2.26 (2)	3.038 (3)	161 (4)
O2—H2A···O1	0.81 (1)	2.24 (4)	2.653 (4)	112 (4)

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

Experimental details

Crystal data
Chemical formula	C₁₀H₆Br₂O₂
M_r	317.96
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	5.0928 (9), 11.932 (2), 15.779 (3)
V (Å³)	958.9 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	8.42
Crystal size (mm)	0.16 × 0.12 × 0.10

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.356, 0.486
No. of measured, independent and observed [I > 2σ(I)] reflections	6339, 2363, 2156
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.068, 1.00
No. of reflections	2363
No. of parameters	133
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.40
Absolute structure	Flack (1983), 899 Friedel pairs
Absolute structure parameter	0.034 (15)

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···Cg1ⁱ	0.819 (10)	2.94 (5)	3.441 (3)	122 (4)
O2—H2A···O2ⁱⁱ	0.810 (10)	2.261 (17)	3.038 (3)	161 (4)
O2—H2A···O1	0.810 (10)	2.24 (4)	2.653 (4)	112 (4)

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

Acknowledgements

The authors are grateful to the Central China Normal University for financial support and thank Qi Li for the X-ray data collection.

References

Ahn, P. D., Bishop, R., Craig, D. C. & Scudder, M. L. (2009). Acta Cryst. E65, o636. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2001). SAINT-Plus, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Lai, Y.-H. & Yap, A. H.-T. (1993). J. Chem. Soc. Perkin Trans. 2, pp. 1373–1377. CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2009

doi:10.1107/S1600536811026997

Open

access