2-[(5,7-Dibromo-quinolin-8-yl)-oxy]-N-(2-meth-oxy-phen-yl)acetamide.

In the title compound, C(18)H(14)Br(2)N(2)O(3), an intra-molecular N-H⋯N hydrogen bond forms an eight-membered ring. The dihedral angle between the planes of the quinoline system and the benzene ring is 41.69 (1)°. The crystal packing is stabilized by inter-molecular C-H⋯O hydrogen bonds and short Br⋯O inter-actions [3.0079 (19) Å].

Related literature

The structure of N,N-dicyclo­hexyl-2-(5,7-dibromo­quinolin-8-yl­oxy)acetamide has been reported by Liu et al. (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶). For applications of 8-hy­droxy­quinoline and its derivatives, see: Bratzel et al. (1972 ▶). Some 8-hy­droxy­quinoline derivatives and their trans­ition metal complexes exhibit anti­bacterial activity, see: Patel & Patel (1999 ▶).

Experimental

Crystal data

C18H14Br2N2O3

M = 466.13

Monoclinic,

a = 8.7570 (18) Å

b = 8.7279 (17) Å

c = 22.372 (5) Å

β = 98.04 (3)°

V = 1693.1 (6) Å3

Z = 4

Mo Kα radiation

μ = 4.81 mm−1

T = 293 K

0.06 × 0.02 × 0.02 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.761, T max = 0.910

12864 measured reflections

4027 independent reflections

3316 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.093

S = 1.06

4027 reflections

231 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.83 e Å−3

Δρmin = −0.71 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810048312/hg2753sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048312/hg2753Isup2.hkl

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

C18H14Br2N2O3	F(000) = 920
Mr = 466.13	Dx = 1.829 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4165 reflections
a = 8.7570 (18) Å	θ = 1.8–27.9°
b = 8.7279 (17) Å	µ = 4.81 mm−1
c = 22.372 (5) Å	T = 293 K
β = 98.04 (3)°	Column, colourless
V = 1693.1 (6) Å3	0.06 × 0.02 × 0.02 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	4027 independent reflections
Radiation source: fine-focus sealed tube	3316 reflections with I > 2σ(I)
graphite	Rint = 0.057
phi and ω scans	θmax = 27.9°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.761, Tmax = 0.910	k = −11→8
12864 measured reflections	l = −29→28

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0337P)2 + 1.4595P] where P = (Fo2 + 2Fc2)/3
4027 reflections	(Δ/σ)max = 0.005
231 parameters	Δρmax = 0.83 e Å−3
1 restraint	Δρmin = −0.71 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	0.77254 (3)	0.41089 (3)	1.064695 (11)	0.01979 (6)
Br2	0.16180 (3)	0.18905 (3)	1.014627 (12)	0.02468 (7)
O1	0.81081 (18)	0.22709 (18)	0.94999 (7)	0.0173 (4)
O2	1.0293 (2)	0.39129 (19)	0.84558 (8)	0.0241 (4)
O3	0.8399 (2)	−0.13107 (19)	0.82222 (8)	0.0262 (5)
N2	0.9123 (2)	0.1556 (2)	0.84366 (9)	0.0171 (5)
N1	0.5971 (2)	0.0662 (2)	0.87776 (9)	0.0190 (5)
C1	0.6236 (3)	0.2953 (3)	1.01398 (11)	0.0171 (5)
C2	0.4727 (3)	0.2851 (3)	1.02927 (11)	0.0180 (5)
H2	0.4474	0.3365	1.0630	0.022*
C3	0.3646 (3)	0.1998 (3)	0.99438 (11)	0.0189 (6)
C4	0.3988 (3)	0.1219 (3)	0.94234 (11)	0.0168 (5)
C5	0.2943 (3)	0.0290 (3)	0.90434 (11)	0.0203 (6)
H5	0.1941	0.0150	0.9127	0.024*
C6	0.3416 (3)	−0.0401 (3)	0.85523 (12)	0.0222 (6)
H6	0.2736	−0.1005	0.8297	0.027*
C7	0.4956 (3)	−0.0190 (3)	0.84358 (11)	0.0185 (6)
H7	0.5262	−0.0676	0.8102	0.022*
C8	0.5505 (3)	0.1348 (3)	0.92702 (11)	0.0167 (5)
C9	0.6633 (3)	0.2237 (3)	0.96423 (10)	0.0144 (5)
C10	0.8431 (3)	0.3518 (3)	0.91172 (11)	0.0199 (6)
H10A	0.8976	0.4317	0.9362	0.024*
H10B	0.7467	0.3946	0.8920	0.024*
C11	0.9396 (3)	0.3002 (3)	0.86413 (11)	0.0167 (5)
C12	0.9771 (3)	0.0828 (3)	0.79679 (11)	0.0171 (6)
C13	1.0774 (3)	0.1524 (3)	0.76220 (11)	0.0219 (6)
H13	1.1071	0.2536	0.7697	0.026*
C14	1.1340 (3)	0.0712 (3)	0.71627 (12)	0.0267 (7)
H14	1.2012	0.1188	0.6934	0.032*
C15	1.0912 (3)	−0.0787 (3)	0.70449 (12)	0.0270 (7)
H15	1.1279	−0.1317	0.6733	0.032*
C16	0.9923 (3)	−0.1508 (3)	0.73961 (12)	0.0244 (6)
H16	0.9645	−0.2526	0.7322	0.029*
C17	0.9358 (3)	−0.0713 (3)	0.78527 (11)	0.0194 (6)
C18	0.8150 (3)	−0.2923 (3)	0.82018 (13)	0.0284 (7)
H18A	0.7705	−0.3216	0.7801	0.043*
H18B	0.7460	−0.3198	0.8482	0.043*
H18C	0.9116	−0.3443	0.8308	0.043*
H2A	0.8405 (13)	0.106 (2)	0.8612 (8)	0.032 (8)*

	U11	U22	U33	U12	U13	U23
Br1	0.02090 (11)	0.02052 (12)	0.01835 (12)	−0.00516 (10)	0.00418 (10)	−0.00258 (10)
Br2	0.01560 (11)	0.02843 (13)	0.03130 (14)	−0.00014 (10)	0.00784 (10)	0.00388 (11)
O1	0.0136 (7)	0.0182 (8)	0.0208 (8)	−0.0006 (7)	0.0048 (7)	0.0022 (7)
O2	0.0284 (9)	0.0165 (8)	0.0304 (10)	−0.0091 (7)	0.0149 (8)	−0.0046 (7)
O3	0.0305 (9)	0.0132 (8)	0.0377 (10)	−0.0036 (7)	0.0139 (8)	−0.0035 (8)
N2	0.0194 (9)	0.0132 (9)	0.0200 (10)	0.0007 (8)	0.0076 (8)	0.0011 (8)
N1	0.0197 (10)	0.0200 (10)	0.0168 (10)	0.0022 (8)	0.0012 (9)	0.0018 (8)
C1	0.0177 (11)	0.0161 (11)	0.0175 (12)	0.0000 (9)	0.0019 (9)	0.0037 (9)
C2	0.0178 (11)	0.0173 (11)	0.0209 (12)	0.0003 (9)	0.0096 (10)	0.0026 (10)
C3	0.0159 (11)	0.0180 (11)	0.0232 (12)	0.0030 (9)	0.0044 (10)	0.0098 (10)
C4	0.0151 (10)	0.0173 (11)	0.0172 (12)	0.0031 (9)	−0.0006 (9)	0.0085 (10)
C5	0.0160 (11)	0.0179 (11)	0.0261 (13)	−0.0019 (10)	0.0000 (10)	0.0044 (10)
C6	0.0220 (12)	0.0176 (12)	0.0250 (13)	−0.0035 (10)	−0.0038 (11)	0.0029 (10)
C7	0.0252 (12)	0.0149 (11)	0.0143 (11)	−0.0027 (10)	−0.0008 (10)	−0.0010 (10)
C8	0.0202 (11)	0.0138 (10)	0.0161 (11)	0.0007 (9)	0.0025 (10)	0.0048 (9)
C9	0.0117 (10)	0.0141 (11)	0.0175 (11)	0.0006 (9)	0.0030 (9)	0.0035 (9)
C10	0.0242 (12)	0.0127 (11)	0.0247 (12)	−0.0028 (10)	0.0099 (10)	−0.0012 (10)
C11	0.0152 (10)	0.0158 (11)	0.0191 (12)	0.0012 (9)	0.0024 (9)	0.0012 (10)
C12	0.0200 (11)	0.0160 (11)	0.0138 (11)	0.0025 (9)	−0.0023 (10)	0.0001 (9)
C13	0.0245 (12)	0.0184 (12)	0.0230 (13)	0.0010 (10)	0.0046 (11)	0.0030 (10)
C14	0.0328 (14)	0.0299 (14)	0.0193 (13)	0.0003 (12)	0.0105 (11)	0.0010 (11)
C15	0.0327 (14)	0.0300 (14)	0.0184 (13)	0.0084 (12)	0.0040 (11)	−0.0057 (11)
C16	0.0288 (13)	0.0183 (12)	0.0261 (13)	0.0028 (11)	0.0031 (11)	−0.0082 (11)
C17	0.0188 (11)	0.0197 (12)	0.0188 (12)	0.0018 (10)	−0.0009 (10)	−0.0010 (10)
C18	0.0332 (14)	0.0164 (12)	0.0357 (15)	−0.0043 (11)	0.0055 (13)	−0.0017 (11)

Br1—C1	1.895 (2)	C6—C7	1.420 (4)
Br2—C3	1.896 (2)	C6—H6	0.9300
O1—C9	1.374 (3)	C7—H7	0.9300
O1—C10	1.437 (3)	C8—C9	1.429 (3)
O2—C11	1.230 (3)	C10—C11	1.518 (3)
O3—C17	1.362 (3)	C10—H10A	0.9700
O3—C18	1.424 (3)	C10—H10B	0.9700
N2—C11	1.352 (3)	C12—C13	1.389 (4)
N2—C12	1.411 (3)	C12—C17	1.407 (3)
N2—H2A	0.898 (9)	C13—C14	1.395 (4)
N1—C7	1.318 (3)	C13—H13	0.9300
N1—C8	1.366 (3)	C14—C15	1.376 (4)
C1—C9	1.363 (3)	C14—H14	0.9300
C1—C2	1.414 (3)	C15—C16	1.398 (4)
C2—C3	1.361 (3)	C15—H15	0.9300
C2—H2	0.9300	C16—C17	1.383 (4)
C3—C4	1.416 (3)	C16—H16	0.9300
C4—C5	1.415 (3)	C18—H18A	0.9600
C4—C8	1.421 (3)	C18—H18B	0.9600
C5—C6	1.368 (4)	C18—H18C	0.9600
C5—H5	0.9300
C9—O1—C10	115.11 (17)	O1—C10—C11	111.60 (19)
C17—O3—C18	117.6 (2)	O1—C10—H10A	109.3
C11—N2—C12	127.0 (2)	C11—C10—H10A	109.3
C11—N2—H2A	113.8 (14)	O1—C10—H10B	109.3
C12—N2—H2A	119.1 (14)	C11—C10—H10B	109.3
C7—N1—C8	117.5 (2)	H10A—C10—H10B	108.0
C9—C1—C2	121.5 (2)	O2—C11—N2	125.5 (2)
C9—C1—Br1	120.03 (18)	O2—C11—C10	119.3 (2)
C2—C1—Br1	118.47 (18)	N2—C11—C10	115.2 (2)
C3—C2—C1	119.6 (2)	C13—C12—C17	118.8 (2)
C3—C2—H2	120.2	C13—C12—N2	124.7 (2)
C1—C2—H2	120.2	C17—C12—N2	116.5 (2)
C2—C3—C4	121.6 (2)	C12—C13—C14	120.4 (2)
C2—C3—Br2	119.32 (19)	C12—C13—H13	119.8
C4—C3—Br2	119.06 (17)	C14—C13—H13	119.8
C5—C4—C3	125.1 (2)	C15—C14—C13	120.6 (3)
C5—C4—C8	116.7 (2)	C15—C14—H14	119.7
C3—C4—C8	118.2 (2)	C13—C14—H14	119.7
C6—C5—C4	119.5 (2)	C14—C15—C16	119.6 (3)
C6—C5—H5	120.3	C14—C15—H15	120.2
C4—C5—H5	120.3	C16—C15—H15	120.2
C5—C6—C7	119.5 (2)	C17—C16—C15	120.2 (2)
C5—C6—H6	120.3	C17—C16—H16	119.9
C7—C6—H6	120.3	C15—C16—H16	119.9
N1—C7—C6	123.2 (2)	O3—C17—C16	124.8 (2)
N1—C7—H7	118.4	O3—C17—C12	114.8 (2)
C6—C7—H7	118.4	C16—C17—C12	120.4 (2)
N1—C8—C4	123.7 (2)	O3—C18—H18A	109.5
N1—C8—C9	116.6 (2)	O3—C18—H18B	109.5
C4—C8—C9	119.7 (2)	H18A—C18—H18B	109.5
C1—C9—O1	122.3 (2)	O3—C18—H18C	109.5
C1—C9—C8	119.4 (2)	H18A—C18—H18C	109.5
O1—C9—C8	118.2 (2)	H18B—C18—H18C	109.5
C9—C1—C2—C3	1.2 (4)	N1—C8—C9—C1	179.8 (2)
Br1—C1—C2—C3	−178.45 (18)	C4—C8—C9—C1	−0.2 (3)
C1—C2—C3—C4	−0.8 (4)	N1—C8—C9—O1	−3.4 (3)
C1—C2—C3—Br2	−179.18 (17)	C4—C8—C9—O1	176.6 (2)
C2—C3—C4—C5	178.9 (2)	C9—O1—C10—C11	−138.9 (2)
Br2—C3—C4—C5	−2.8 (3)	C12—N2—C11—O2	−1.6 (4)
C2—C3—C4—C8	0.0 (3)	C12—N2—C11—C10	175.2 (2)
Br2—C3—C4—C8	178.33 (17)	O1—C10—C11—O2	−149.5 (2)
C3—C4—C5—C6	179.9 (2)	O1—C10—C11—N2	33.5 (3)
C8—C4—C5—C6	−1.2 (3)	C11—N2—C12—C13	−2.4 (4)
C4—C5—C6—C7	0.7 (4)	C11—N2—C12—C17	177.4 (2)
C8—N1—C7—C6	0.9 (3)	C17—C12—C13—C14	1.0 (4)
C5—C6—C7—N1	−0.6 (4)	N2—C12—C13—C14	−179.2 (2)
C7—N1—C8—C4	−1.4 (3)	C12—C13—C14—C15	0.1 (4)
C7—N1—C8—C9	178.6 (2)	C13—C14—C15—C16	−1.1 (4)
C5—C4—C8—N1	1.6 (3)	C14—C15—C16—C17	1.1 (4)
C3—C4—C8—N1	−179.4 (2)	C18—O3—C17—C16	10.3 (3)
C5—C4—C8—C9	−178.5 (2)	C18—O3—C17—C12	−169.3 (2)
C3—C4—C8—C9	0.5 (3)	C15—C16—C17—O3	−179.5 (2)
C2—C1—C9—O1	−177.3 (2)	C15—C16—C17—C12	0.0 (4)
Br1—C1—C9—O1	2.3 (3)	C13—C12—C17—O3	178.5 (2)
C2—C1—C9—C8	−0.7 (3)	N2—C12—C17—O3	−1.3 (3)
Br1—C1—C9—C8	178.94 (17)	C13—C12—C17—C16	−1.1 (4)
C10—O1—C9—C1	−90.4 (3)	N2—C12—C17—C16	179.1 (2)
C10—O1—C9—C8	92.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1	0.90 (1)	2.24 (1)	3.065 (3)	153 (1)
C18—H18C···O2i	0.96	2.53	3.342 (3)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯N1	0.90 (1)	2.24 (1)	3.065 (3)	153 (1)
C18—H18C⋯O2i	0.96	2.53	3.342 (3)	142

Symmetry code: (i) .