1-(6,8-Dibromo-2-methyl-quinolin-3-yl)ethanone.

Two independent mol-ecules,1 and 2, with similar conformations comprise the asymmetric unit in the title compound, C(12)H(9)Br(2)NO. The major difference between the mol-ecules relates to the relative orientation of the ketone-methyl groups [the C-C-C-C torsion angles are -1.7 (6) and -16.8 (6)° for mol-ecules 1 and 2, respectively]; in each case, the ketone O atom is directed towards the ring-bound methyl group. The crystal packing comprises layers of mol-ecules, sustained by C-H⋯O and π-π {ring centroid(C(6)) of molecule 2 with NC(5) of molecule 1 [3.584 (3) Å] and NC(5) of molecule 2 [3.615 (3) Å]} interactions. C-H⋯Br contacts also occur.

Related literature

For background details and the biological applications of quinolines, see: Kalluraya & Sreenivasa (1998 ▶); Xiang et al. (2006 ▶). For a related structure, see: Prasath et al. (2011 ▶). For additional structure analysis, see: Spek (2009 ▶).

Experimental

Crystal data

C12H9Br2NO

M = 343.02

Triclinic,

a = 9.7549 (5) Å

b = 11.1719 (6) Å

c = 11.5629 (5) Å

α = 99.043 (4)°

β = 93.330 (4)°

γ = 111.733 (5)°

V = 1146.69 (10) Å3

Z = 4

Cu Kα radiation

μ = 8.78 mm−1

T = 100 K

0.25 × 0.20 × 0.15 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.218, T max = 0.353

6906 measured reflections

4462 independent reflections

4281 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.139

S = 1.11

4462 reflections

293 parameters

H-atom parameters constrained

Δρmax = 1.60 e Å−3

Δρmin = −1.38 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶), DIAMOND (Brandenburg, 2006 ▶) and Qmol (Gans & Shalloway, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811037044/hb6406sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811037044/hb6406Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811037044/hb6406Isup3.cml

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

C12H9Br2NO	Z = 4
Mr = 343.02	F(000) = 664
Triclinic, P1	Dx = 1.987 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 9.7549 (5) Å	Cell parameters from 4985 reflections
b = 11.1719 (6) Å	θ = 3.9–74.1°
c = 11.5629 (5) Å	µ = 8.78 mm−1
α = 99.043 (4)°	T = 100 K
β = 93.330 (4)°	Prism, light-brown
γ = 111.733 (5)°	0.25 × 0.20 × 0.15 mm
V = 1146.69 (10) Å3

Agilent SuperNova Dual diffractometer with an Atlas detector	4462 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	4281 reflections with I > 2σ(I)
Mirror	Rint = 0.039
Detector resolution: 10.4041 pixels mm-1	θmax = 74.3°, θmin = 3.9°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −13→13
Tmin = 0.218, Tmax = 0.353	l = −14→7
6906 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0872P)2 + 3.5949P] where P = (Fo2 + 2Fc2)/3
4462 reflections	(Δ/σ)max = 0.001
293 parameters	Δρmax = 1.60 e Å−3
0 restraints	Δρmin = −1.38 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	0.64524 (5)	0.65200 (5)	0.49508 (4)	0.01426 (16)
Br2	0.92320 (5)	1.16226 (5)	0.40306 (4)	0.01406 (16)
Br3	0.85223 (5)	0.34850 (5)	1.00127 (4)	0.01197 (15)
Br4	0.24944 (5)	0.00166 (4)	0.93076 (4)	0.01288 (15)
O1	−0.0502 (4)	0.7000 (4)	0.2695 (3)	0.0221 (8)
O2	0.5755 (4)	0.8053 (4)	0.7753 (3)	0.0192 (8)
N1	0.3618 (4)	0.6815 (4)	0.3952 (3)	0.0095 (7)
N2	0.7242 (4)	0.5237 (4)	0.8901 (3)	0.0081 (7)
C1	0.4870 (5)	0.7915 (4)	0.3957 (4)	0.0080 (8)
C2	0.6289 (5)	0.7963 (4)	0.4388 (4)	0.0096 (8)
C3	0.7562 (5)	0.9045 (5)	0.4393 (4)	0.0112 (9)
H3	0.8503	0.9061	0.4678	0.013*
C4	0.7460 (5)	1.0134 (4)	0.3971 (4)	0.0092 (9)
C5	0.6127 (5)	1.0128 (5)	0.3557 (4)	0.0134 (9)
H5	0.6077	1.0865	0.3271	0.016*
C6	0.4816 (5)	0.9023 (5)	0.3553 (4)	0.0107 (9)
C7	0.3414 (5)	0.8974 (5)	0.3137 (4)	0.0117 (9)
H7	0.3340	0.9701	0.2849	0.014*
C8	0.2144 (5)	0.7890 (5)	0.3138 (4)	0.0103 (9)
C9	0.2302 (5)	0.6785 (4)	0.3544 (4)	0.0084 (8)
C10	0.1013 (5)	0.5530 (5)	0.3547 (4)	0.0165 (10)
H10A	0.1373	0.4915	0.3852	0.025*
H10B	0.0511	0.5143	0.2740	0.025*
H10C	0.0311	0.5710	0.4051	0.025*
C11	0.0666 (5)	0.7922 (5)	0.2724 (4)	0.0141 (10)
C12	0.0674 (6)	0.9161 (5)	0.2366 (6)	0.0250 (12)
H12A	−0.0349	0.9111	0.2240	0.037*
H12B	0.1125	0.9265	0.1634	0.037*
H12C	0.1252	0.9916	0.2992	0.037*
C13	0.6151 (5)	0.4096 (4)	0.9012 (4)	0.0071 (8)
C14	0.6509 (5)	0.3130 (5)	0.9490 (4)	0.0095 (8)
C15	0.5430 (5)	0.1943 (4)	0.9581 (4)	0.0099 (8)
H15	0.5698	0.1309	0.9890	0.012*
C16	0.3936 (5)	0.1679 (5)	0.9212 (4)	0.0104 (9)
C17	0.3516 (5)	0.2581 (4)	0.8784 (4)	0.0084 (8)
H17	0.2495	0.2398	0.8563	0.010*
C18	0.4625 (5)	0.3792 (4)	0.8676 (4)	0.0093 (8)
C19	0.4264 (5)	0.4746 (4)	0.8214 (4)	0.0089 (8)
H19	0.3252	0.4584	0.7980	0.011*
C20	0.5357 (5)	0.5907 (4)	0.8098 (4)	0.0097 (8)
C21	0.6871 (5)	0.6116 (4)	0.8459 (4)	0.0093 (8)
C22	0.8165 (5)	0.7332 (5)	0.8342 (4)	0.0146 (9)
H22A	0.9094	0.7198	0.8477	0.022*
H22B	0.8186	0.8079	0.8925	0.022*
H22C	0.8057	0.7512	0.7546	0.022*
C23	0.4916 (6)	0.6915 (5)	0.7634 (4)	0.0134 (9)
C24	0.3351 (6)	0.6467 (5)	0.7000 (4)	0.0173 (10)
H24A	0.3369	0.6938	0.6351	0.026*
H24B	0.2702	0.6652	0.7557	0.026*
H24C	0.2972	0.5521	0.6685	0.026*

	U11	U22	U33	U12	U13	U23
Br1	0.0141 (3)	0.0157 (3)	0.0155 (3)	0.0064 (2)	−0.00005 (19)	0.0089 (2)
Br2	0.0070 (3)	0.0118 (3)	0.0201 (3)	−0.0001 (2)	0.00311 (18)	0.0024 (2)
Br3	0.0070 (3)	0.0125 (3)	0.0165 (3)	0.0031 (2)	−0.00128 (18)	0.00586 (19)
Br4	0.0103 (3)	0.0077 (3)	0.0200 (3)	0.00088 (19)	0.00047 (18)	0.00814 (19)
O1	0.0065 (16)	0.029 (2)	0.029 (2)	0.0018 (15)	0.0026 (14)	0.0116 (16)
O2	0.0233 (19)	0.0126 (17)	0.0236 (18)	0.0072 (15)	0.0012 (15)	0.0084 (14)
N1	0.0104 (18)	0.0121 (19)	0.0070 (16)	0.0043 (15)	0.0040 (14)	0.0041 (14)
N2	0.0091 (17)	0.0099 (18)	0.0050 (16)	0.0028 (15)	0.0022 (13)	0.0020 (14)
C1	0.012 (2)	0.009 (2)	0.0046 (18)	0.0048 (18)	0.0032 (15)	0.0024 (15)
C2	0.012 (2)	0.012 (2)	0.0048 (18)	0.0042 (18)	0.0013 (15)	0.0031 (16)
C3	0.009 (2)	0.015 (2)	0.012 (2)	0.0071 (18)	0.0010 (16)	0.0048 (17)
C4	0.010 (2)	0.007 (2)	0.011 (2)	0.0027 (17)	0.0027 (16)	0.0020 (16)
C5	0.012 (2)	0.014 (2)	0.015 (2)	0.0051 (19)	0.0035 (17)	0.0044 (18)
C6	0.007 (2)	0.015 (2)	0.0092 (19)	0.0044 (18)	0.0032 (16)	0.0018 (17)
C7	0.015 (2)	0.013 (2)	0.011 (2)	0.0076 (19)	0.0046 (17)	0.0044 (17)
C8	0.007 (2)	0.017 (2)	0.0076 (19)	0.0062 (18)	0.0015 (15)	0.0032 (17)
C9	0.010 (2)	0.010 (2)	0.0053 (18)	0.0023 (18)	0.0031 (15)	0.0031 (16)
C10	0.008 (2)	0.015 (2)	0.018 (2)	−0.0032 (19)	0.0038 (18)	−0.0005 (19)
C11	0.012 (2)	0.019 (2)	0.011 (2)	0.006 (2)	0.0016 (17)	0.0012 (18)
C12	0.013 (2)	0.017 (3)	0.050 (4)	0.010 (2)	0.003 (2)	0.008 (2)
C13	0.0066 (19)	0.008 (2)	0.0073 (18)	0.0032 (17)	0.0016 (15)	0.0015 (15)
C14	0.008 (2)	0.015 (2)	0.0061 (19)	0.0050 (18)	0.0001 (15)	0.0017 (16)
C15	0.012 (2)	0.0070 (19)	0.014 (2)	0.0060 (18)	0.0008 (17)	0.0062 (16)
C16	0.009 (2)	0.009 (2)	0.012 (2)	0.0013 (18)	0.0022 (16)	0.0028 (17)
C17	0.007 (2)	0.009 (2)	0.011 (2)	0.0048 (17)	0.0006 (15)	0.0047 (16)
C18	0.014 (2)	0.012 (2)	0.0048 (18)	0.0062 (18)	0.0027 (16)	0.0047 (16)
C19	0.013 (2)	0.009 (2)	0.0063 (19)	0.0060 (18)	0.0003 (16)	0.0017 (16)
C20	0.018 (2)	0.008 (2)	0.0054 (18)	0.0063 (18)	0.0031 (16)	0.0024 (16)
C21	0.014 (2)	0.010 (2)	0.0042 (18)	0.0040 (18)	0.0036 (16)	0.0026 (16)
C22	0.014 (2)	0.012 (2)	0.016 (2)	0.0012 (19)	0.0046 (18)	0.0093 (18)
C23	0.019 (2)	0.016 (2)	0.011 (2)	0.010 (2)	0.0049 (18)	0.0086 (18)
C24	0.018 (2)	0.016 (2)	0.021 (2)	0.008 (2)	0.0006 (19)	0.0103 (19)

Br1—C2	1.886 (5)	C10—H10C	0.9800
Br2—C4	1.892 (5)	C11—C12	1.503 (7)
Br3—C14	1.895 (4)	C12—H12A	0.9800
Br4—C16	1.894 (5)	C12—H12B	0.9800
O1—C11	1.215 (6)	C12—H12C	0.9800
O2—C23	1.211 (6)	C13—C18	1.414 (6)
N1—C9	1.328 (6)	C13—C14	1.426 (6)
N1—C1	1.374 (6)	C14—C15	1.379 (6)
N2—C21	1.324 (6)	C15—C16	1.401 (6)
N2—C13	1.355 (6)	C15—H15	0.9500
C1—C6	1.407 (6)	C16—C17	1.366 (6)
C1—C2	1.422 (6)	C17—C18	1.415 (6)
C2—C3	1.374 (7)	C17—H17	0.9500
C3—C4	1.413 (6)	C18—C19	1.407 (6)
C3—H3	0.9500	C19—C20	1.373 (6)
C4—C5	1.357 (7)	C19—H19	0.9500
C5—C6	1.410 (7)	C20—C21	1.433 (7)
C5—H5	0.9500	C20—C23	1.505 (6)
C6—C7	1.402 (7)	C21—C22	1.505 (6)
C7—C8	1.375 (7)	C22—H22A	0.9800
C7—H7	0.9500	C22—H22B	0.9800
C8—C9	1.443 (6)	C22—H22C	0.9800
C8—C11	1.508 (6)	C23—C24	1.519 (7)
C9—C10	1.499 (6)	C24—H24A	0.9800
C10—H10A	0.9800	C24—H24B	0.9800
C10—H10B	0.9800	C24—H24C	0.9800
C9—N1—C1	119.1 (4)	H12B—C12—H12C	109.5
C21—N2—C13	118.9 (4)	N2—C13—C18	123.0 (4)
N1—C1—C6	122.5 (4)	N2—C13—C14	120.4 (4)
N1—C1—C2	119.9 (4)	C18—C13—C14	116.5 (4)
C6—C1—C2	117.6 (4)	C15—C14—C13	121.8 (4)
C3—C2—C1	121.2 (4)	C15—C14—Br3	119.0 (3)
C3—C2—Br1	118.7 (3)	C13—C14—Br3	119.2 (3)
C1—C2—Br1	120.1 (3)	C14—C15—C16	119.4 (4)
C2—C3—C4	119.5 (4)	C14—C15—H15	120.3
C2—C3—H3	120.3	C16—C15—H15	120.3
C4—C3—H3	120.3	C17—C16—C15	121.6 (4)
C5—C4—C3	121.1 (4)	C17—C16—Br4	120.3 (4)
C5—C4—Br2	120.6 (4)	C15—C16—Br4	118.1 (3)
C3—C4—Br2	118.2 (3)	C16—C17—C18	119.0 (4)
C4—C5—C6	119.7 (4)	C16—C17—H17	120.5
C4—C5—H5	120.2	C18—C17—H17	120.5
C6—C5—H5	120.2	C19—C18—C17	121.6 (4)
C7—C6—C1	117.3 (4)	C19—C18—C13	116.8 (4)
C7—C6—C5	121.7 (4)	C17—C18—C13	121.6 (4)
C1—C6—C5	121.0 (4)	C20—C19—C18	120.8 (4)
C8—C7—C6	121.1 (4)	C20—C19—H19	119.6
C8—C7—H7	119.4	C18—C19—H19	119.6
C6—C7—H7	119.4	C19—C20—C21	118.1 (4)
C7—C8—C9	118.0 (4)	C19—C20—C23	118.9 (4)
C7—C8—C11	118.4 (4)	C21—C20—C23	122.9 (4)
C9—C8—C11	123.6 (4)	N2—C21—C20	122.4 (4)
N1—C9—C8	121.9 (4)	N2—C21—C22	114.8 (4)
N1—C9—C10	114.9 (4)	C20—C21—C22	122.8 (4)
C8—C9—C10	123.2 (4)	C21—C22—H22A	109.5
C9—C10—H10A	109.5	C21—C22—H22B	109.5
C9—C10—H10B	109.5	H22A—C22—H22B	109.5
H10A—C10—H10B	109.5	C21—C22—H22C	109.5
C9—C10—H10C	109.5	H22A—C22—H22C	109.5
H10A—C10—H10C	109.5	H22B—C22—H22C	109.5
H10B—C10—H10C	109.5	O2—C23—C20	122.5 (4)
O1—C11—C12	120.3 (5)	O2—C23—C24	119.7 (4)
O1—C11—C8	122.1 (5)	C20—C23—C24	117.8 (4)
C12—C11—C8	117.5 (4)	C23—C24—H24A	109.5
C11—C12—H12A	109.5	C23—C24—H24B	109.5
C11—C12—H12B	109.5	H24A—C24—H24B	109.5
H12A—C12—H12B	109.5	C23—C24—H24C	109.5
C11—C12—H12C	109.5	H24A—C24—H24C	109.5
H12A—C12—H12C	109.5	H24B—C24—H24C	109.5
C9—N1—C1—C6	0.4 (6)	C21—N2—C13—C18	0.2 (6)
C9—N1—C1—C2	−179.8 (4)	C21—N2—C13—C14	−179.6 (4)
N1—C1—C2—C3	179.3 (4)	N2—C13—C14—C15	−177.9 (4)
C6—C1—C2—C3	−0.9 (6)	C18—C13—C14—C15	2.3 (6)
N1—C1—C2—Br1	0.0 (5)	N2—C13—C14—Br3	1.9 (5)
C6—C1—C2—Br1	179.8 (3)	C18—C13—C14—Br3	−177.9 (3)
C1—C2—C3—C4	0.5 (6)	C13—C14—C15—C16	−1.1 (7)
Br1—C2—C3—C4	179.8 (3)	Br3—C14—C15—C16	179.1 (3)
C2—C3—C4—C5	−0.2 (7)	C14—C15—C16—C17	−1.2 (7)
C2—C3—C4—Br2	178.4 (3)	C14—C15—C16—Br4	178.2 (3)
C3—C4—C5—C6	0.4 (7)	C15—C16—C17—C18	2.1 (7)
Br2—C4—C5—C6	−178.1 (3)	Br4—C16—C17—C18	−177.3 (3)
N1—C1—C6—C7	0.2 (6)	C16—C17—C18—C19	178.4 (4)
C2—C1—C6—C7	−179.6 (4)	C16—C17—C18—C13	−0.8 (6)
N1—C1—C6—C5	−179.2 (4)	N2—C13—C18—C19	−0.4 (6)
C2—C1—C6—C5	1.1 (6)	C14—C13—C18—C19	179.4 (4)
C4—C5—C6—C7	179.8 (4)	N2—C13—C18—C17	178.8 (4)
C4—C5—C6—C1	−0.9 (7)	C14—C13—C18—C17	−1.3 (6)
C1—C6—C7—C8	0.7 (7)	C17—C18—C19—C20	−179.0 (4)
C5—C6—C7—C8	−180.0 (4)	C13—C18—C19—C20	0.3 (6)
C6—C7—C8—C9	−2.0 (6)	C18—C19—C20—C21	0.1 (6)
C6—C7—C8—C11	177.6 (4)	C18—C19—C20—C23	−178.2 (4)
C1—N1—C9—C8	−1.9 (6)	C13—N2—C21—C20	0.2 (6)
C1—N1—C9—C10	178.5 (4)	C13—N2—C21—C22	−178.4 (4)
C7—C8—C9—N1	2.7 (6)	C19—C20—C21—N2	−0.4 (6)
C11—C8—C9—N1	−176.9 (4)	C23—C20—C21—N2	177.9 (4)
C7—C8—C9—C10	−177.7 (4)	C19—C20—C21—C22	178.2 (4)
C11—C8—C9—C10	2.7 (7)	C23—C20—C21—C22	−3.6 (6)
C7—C8—C11—O1	179.7 (4)	C19—C20—C23—O2	162.9 (5)
C9—C8—C11—O1	−0.7 (7)	C21—C20—C23—O2	−15.4 (7)
C7—C8—C11—C12	−1.7 (6)	C19—C20—C23—C24	−16.8 (6)
C9—C8—C11—C12	177.9 (4)	C21—C20—C23—C24	165.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O2i	0.95	2.56	3.453 (7)	157
C15—H15···Br4ii	0.95	2.89	3.796 (5)	160
C19—H19···O1iii	0.95	2.60	3.462 (6)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O2i	0.95	2.56	3.453 (7)	157
C15—H15⋯Br4ii	0.95	2.89	3.796 (5)	160
C19—H19⋯O1iii	0.95	2.60	3.462 (6)	152

Symmetry codes: (i) ; (ii) ; (iii) .