5,7-Dibromo-2-methyl-quinolin-8-ol.

In the title compound, C(10)H(7)Br(2)NO, the mol-ecule possesses a planar geometry with an r.m.s deviation of 0.0383 Å for all non-H atoms. The crystal structure displays O-H⋯N and C-H⋯O hydrogen bonding, as well as Br⋯Br contacts [3.6284 (4) Å].

Related literature

For a review of hy­droxy­quinolines in supra­molecular chemistry, see: Albrecht et al. (2008 ▶). Bei et al. (1997 ▶) report on group 4 metal alkyl complexes. The crystal structure of the parent 8-hy­droxy­quinoline is described by Banerjee & Saha (1986 ▶) and Roychowdhury et al. (1978 ▶). Choi & Chi (2004 ▶) used the title compound as the starting material for alkyl­amino-substituted quinoline-5,8-diones. For halogen inter­actions in mol­ecular crystal structures, see: Awwadi et al. (2006 ▶); Brammer et al. (2001 ▶); Metrangolo et al. (2008 ▶).

Experimental

Crystal data

C10H7Br2NO

M = 316.99

Monoclinic,

a = 22.2221 (5) Å

b = 4.0479 (1) Å

c = 21.7221 (4) Å

β = 102.167 (1)°

V = 1910.07 (7) Å3

Z = 8

Mo Kα radiation

μ = 8.45 mm−1

T = 93 K

0.40 × 0.24 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.133, T max = 0.258

13437 measured reflections

1727 independent reflections

1629 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.017

wR(F 2) = 0.046

S = 1.11

1727 reflections

129 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.60 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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 datablocks global, I. DOI: 10.1107/S1600536811007434/im2267sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811007434/im2267Isup2.hkl

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

C10H7Br2NO	F(000) = 1216
Mr = 316.99	Dx = 2.205 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9610 reflections
a = 22.2221 (5) Å	θ = 2.4–29.2°
b = 4.0479 (1) Å	µ = 8.45 mm−1
c = 21.7221 (4) Å	T = 93 K
β = 102.167 (1)°	Piece, colourless
V = 1910.07 (7) Å3	0.40 × 0.24 × 0.22 mm
Z = 8

Bruker SMART CCD area-detector diffractometer	1727 independent reflections
Radiation source: fine-focus sealed tube	1629 reflections with I > 2σ(I)
graphite	Rint = 0.025
φ and ω scans	θmax = 25.2°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −26→25
Tmin = 0.133, Tmax = 0.258	k = −4→4
13437 measured reflections	l = −26→26

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)] = 0.017	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.046	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0262P)2 + 2.9807P] where P = (Fo2 + 2Fc2)/3
1727 reflections	(Δ/σ)max = 0.001
129 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.60 e Å−3

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	0.226304 (10)	0.34054 (6)	0.083369 (10)	0.02104 (8)
Br2	0.431764 (10)	1.01225 (5)	0.033388 (9)	0.02065 (8)
N1	0.42288 (8)	0.6326 (4)	0.26148 (8)	0.0151 (4)
O1	0.47717 (7)	0.9601 (4)	0.17443 (7)	0.0197 (3)
H1	0.5012	0.8441	0.2009	0.030*
C1	0.39566 (10)	0.4874 (5)	0.30307 (10)	0.0168 (4)
C2	0.33816 (10)	0.3287 (5)	0.28492 (10)	0.0198 (5)
H2	0.3204	0.2213	0.3157	0.024*
C3	0.30807 (10)	0.3291 (5)	0.22338 (10)	0.0186 (5)
H3	0.2693	0.2223	0.2111	0.022*
C4	0.33477 (10)	0.4888 (5)	0.17805 (10)	0.0144 (4)
C5	0.30664 (10)	0.5140 (5)	0.11344 (10)	0.0155 (4)
C6	0.33502 (10)	0.6709 (5)	0.07179 (10)	0.0174 (4)
H6	0.3154	0.6859	0.0286	0.021*
C7	0.39324 (10)	0.8094 (5)	0.09334 (10)	0.0150 (4)
C8	0.42345 (10)	0.8007 (5)	0.15583 (10)	0.0145 (4)
C9	0.39347 (10)	0.6360 (5)	0.19921 (9)	0.0137 (4)
C10	0.42720 (11)	0.4996 (6)	0.37143 (10)	0.0224 (5)
H10A	0.4668	0.3840	0.3774	0.034*
H10B	0.4012	0.3923	0.3968	0.034*
H10C	0.4342	0.7303	0.3847	0.034*

	U11	U22	U33	U12	U13	U23
Br1	0.01485 (13)	0.02683 (14)	0.02053 (13)	−0.00403 (8)	0.00170 (9)	−0.00389 (8)
Br2	0.02015 (14)	0.02857 (14)	0.01417 (13)	−0.00252 (9)	0.00577 (9)	0.00366 (8)
N1	0.0131 (9)	0.0189 (9)	0.0133 (8)	0.0042 (7)	0.0024 (7)	0.0016 (7)
O1	0.0130 (8)	0.0279 (9)	0.0169 (8)	−0.0037 (6)	0.0001 (6)	0.0048 (6)
C1	0.0168 (11)	0.0181 (11)	0.0160 (10)	0.0068 (8)	0.0048 (9)	0.0025 (8)
C2	0.0196 (12)	0.0220 (12)	0.0198 (11)	0.0029 (9)	0.0088 (9)	0.0040 (9)
C3	0.0142 (11)	0.0193 (11)	0.0233 (11)	0.0004 (8)	0.0063 (9)	0.0011 (9)
C4	0.0124 (11)	0.0144 (10)	0.0172 (11)	0.0037 (8)	0.0045 (8)	−0.0007 (8)
C5	0.0114 (10)	0.0159 (10)	0.0187 (10)	0.0005 (8)	0.0021 (8)	−0.0027 (8)
C6	0.0174 (11)	0.0210 (11)	0.0133 (10)	0.0041 (9)	0.0022 (8)	−0.0015 (8)
C7	0.0157 (11)	0.0168 (10)	0.0143 (10)	0.0023 (8)	0.0071 (8)	0.0017 (8)
C8	0.0113 (10)	0.0153 (10)	0.0174 (10)	0.0032 (8)	0.0039 (8)	0.0003 (8)
C9	0.0131 (11)	0.0152 (10)	0.0130 (10)	0.0043 (8)	0.0030 (8)	−0.0011 (8)
C10	0.0236 (13)	0.0286 (13)	0.0152 (11)	0.0026 (9)	0.0047 (9)	0.0035 (9)

Br1—C5	1.901 (2)	C3—H3	0.9500
Br2—C7	1.890 (2)	C4—C5	1.415 (3)
N1—C1	1.326 (3)	C4—C9	1.420 (3)
N1—C9	1.373 (3)	C5—C6	1.364 (3)
O1—C8	1.342 (3)	C6—C7	1.397 (3)
O1—H1	0.8400	C6—H6	0.9500
C1—C2	1.410 (3)	C7—C8	1.382 (3)
C1—C10	1.503 (3)	C8—C9	1.429 (3)
C2—C3	1.363 (3)	C10—H10A	0.9800
C2—H2	0.9500	C10—H10B	0.9800
C3—C4	1.409 (3)	C10—H10C	0.9800
C1—N1—C9	119.01 (18)	C5—C6—H6	120.3
C8—O1—H1	109.5	C7—C6—H6	120.3
N1—C1—C2	121.88 (19)	C8—C7—C6	122.87 (19)
N1—C1—C10	118.3 (2)	C8—C7—Br2	119.40 (16)
C2—C1—C10	119.8 (2)	C6—C7—Br2	117.73 (15)
C3—C2—C1	120.1 (2)	O1—C8—C7	120.03 (19)
C3—C2—H2	119.9	O1—C8—C9	122.33 (18)
C1—C2—H2	119.9	C7—C8—C9	117.52 (19)
C2—C3—C4	119.6 (2)	N1—C9—C4	121.94 (19)
C2—C3—H3	120.2	N1—C9—C8	117.59 (18)
C4—C3—H3	120.2	C4—C9—C8	120.45 (18)
C3—C4—C5	124.3 (2)	C1—C10—H10A	109.5
C3—C4—C9	117.38 (19)	C1—C10—H10B	109.5
C5—C4—C9	118.34 (19)	H10A—C10—H10B	109.5
C6—C5—C4	121.5 (2)	C1—C10—H10C	109.5
C6—C5—Br1	118.43 (16)	H10A—C10—H10C	109.5
C4—C5—Br1	120.05 (16)	H10B—C10—H10C	109.5
C5—C6—C7	119.32 (19)
C9—N1—C1—C2	1.8 (3)	C6—C7—C8—O1	−174.87 (19)
C9—N1—C1—C10	−177.25 (18)	Br2—C7—C8—O1	5.8 (3)
N1—C1—C2—C3	−1.8 (3)	C6—C7—C8—C9	1.2 (3)
C10—C1—C2—C3	177.2 (2)	Br2—C7—C8—C9	−178.10 (15)
C1—C2—C3—C4	0.0 (3)	C1—N1—C9—C4	0.0 (3)
C2—C3—C4—C5	−177.7 (2)	C1—N1—C9—C8	178.67 (18)
C2—C3—C4—C9	1.6 (3)	C3—C4—C9—N1	−1.7 (3)
C3—C4—C5—C6	−179.7 (2)	C5—C4—C9—N1	177.67 (18)
C9—C4—C5—C6	1.0 (3)	C3—C4—C9—C8	179.69 (19)
C3—C4—C5—Br1	2.5 (3)	C5—C4—C9—C8	−1.0 (3)
C9—C4—C5—Br1	−176.86 (14)	O1—C8—C9—N1	−2.8 (3)
C4—C5—C6—C7	0.1 (3)	C7—C8—C9—N1	−178.78 (18)
Br1—C5—C6—C7	177.96 (15)	O1—C8—C9—C4	175.90 (18)
C5—C6—C7—C8	−1.3 (3)	C7—C8—C9—C4	−0.1 (3)
C5—C6—C7—Br2	178.09 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1i	0.84	1.92	2.707 (2)	157
C10—H10A···O1ii	0.98	2.52	3.342 (3)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1i	0.84	1.92	2.707 (2)	157
C10—H10A⋯O1ii	0.98	2.52	3.342 (3)	141

Symmetry codes: (i) ; (ii) .