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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 12| December 2010| Page o3294
https://doi.org/10.1107/S1600536810048312

2-[(5,7-Di­bromo­quinolin-8-yl)­­oxy]-N-(2-meth­­oxy­phen­yl)acetamide

Yong-Hong Wen,a* Hong-Qing Qina and Hui-Ling Wena

aCollege of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, People's Republic of China
*Correspondence e-mail: wenyyhh@126.com

(Received 15 November 2010; accepted 19 November 2010; online 24 November 2010)

In the title compound, C18H14Br2N2O3, an intra­molecular 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 inter­molecular C—H⋯O hydrogen bonds and short Br⋯O inter­actions [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[Liu, J.-F., Tang, X.-F. & Wen, Y.-H. (2007). Acta Cryst. E63, o4458.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For applications of 8-hy­droxy­quinoline and its derivatives, see: Bratzel et al. (1972[Bratzel, M. P., Aaron, J. J., Winefordner, J. D., Schulman, S. G. & Gershon, H. (1972). Anal. Chem. 44, 1240-1245.]). Some 8-hy­droxy­quinoline derivatives and their trans­ition metal complexes exhibit anti­bacterial activity, see: Patel & Patel (1999[Patel, A. K. & Patel, V. M. (1999). Synth. React. Inorg. Met. Org. Chem. 29, 193-197.]).

[Scheme 1]

Experimental

Crystal data

  • C18H14Br2N2O3

  • Mr = 466.13

  • Monoclinic, P 21 /n

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.761, Tmax = 0.910

  • 12864 measured reflections

  • 4027 independent reflections

  • 3316 reflections with I > 2σ(I)

  • Rint = 0.057
Refinement

  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 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

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) x, y-1, z.

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810048312/hg2753Isup2.hkl

checkCIF report


Comment top

8-Hydroxyquinoline and its derivatives have found extensive application as analytical reagents, e.g. in absorption spectrophotometry, fluorimetry, solvent extraction and partition chromatography (Bratzel et al., 1972). Some 8-hydroxyquinoline derivatives and their complexes with transition metals demonstrate antibacterial activity (Patel & Patel,1999). Recently, the structure of 5,7-dibromosubstituted 8-hydroxyquinolinate amide-type compound, namely N,N-dicyclohexyl-2-(5,7-dibromoquinolin-8-yloxy)acetamide, (II), has been reported (Liu et al., 2007). Here, we have synthesized and carried out the structure determination of the title compound, (I), (Fig. 1).

All bond lengths in (I) are within normal ranges (Allen et al., 1987) and comparable with those in the related compound (II). The sum of the angles around atoms N2 and C11 are 359.9° and 360.0°, respectively, implying a planar configuration. There is one intramolecular hydrogen bond, viz. N2—H2···N1 (Table 1), forming one larger 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 intermolecular C18—H18C···O2 hydrogen bond (Table 1) and Br···O short-contact interactions.

Related literature top

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 top

To a solution of 5,7-dibromo-8-hydroxyquinoline (3.02 g, 10 mmol) in acetone (60 ml) were added 2-chloro-N-(4-methoxyphenyl)acetamide (2.0 g,10 mmol), K2CO3 (1.52 g, 11 mmol) and KI (0.5 g), and the resulting mixture was stirred at 333 K for 5 h. After cooling to room temperature, the mixture was washed three times with water and filtered. Colourless single crystals of (I) suitable for X-ray diffraction study were obtained by slow evaporation of an acetone solution over a period of 6 d.

Refinement top

H atoms were positioned geometrically, with C—H = 0.95–0.99 Å, respectively, and constrained to ride on their parent atoms, with Uiso(H) = 1.2 Ueq(C). The amide proton was refined freely, giving a N—H bond distance of 0.898 (9) Å.

Structure description top

8-Hydroxyquinoline and its derivatives have found extensive application as analytical reagents, e.g. in absorption spectrophotometry, fluorimetry, solvent extraction and partition chromatography (Bratzel et al., 1972). Some 8-hydroxyquinoline derivatives and their complexes with transition metals demonstrate antibacterial activity (Patel & Patel,1999). Recently, the structure of 5,7-dibromosubstituted 8-hydroxyquinolinate amide-type compound, namely N,N-dicyclohexyl-2-(5,7-dibromoquinolin-8-yloxy)acetamide, (II), has been reported (Liu et al., 2007). Here, we have synthesized and carried out the structure determination of the title compound, (I), (Fig. 1).

All bond lengths in (I) are within normal ranges (Allen et al., 1987) and comparable with those in the related compound (II). The sum of the angles around atoms N2 and C11 are 359.9° and 360.0°, respectively, implying a planar configuration. There is one intramolecular hydrogen bond, viz. N2—H2···N1 (Table 1), forming one larger 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 intermolecular C18—H18C···O2 hydrogen bond (Table 1) and Br···O short-contact interactions.

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).

Computing details top

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

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids.
[Figure 2] Fig. 2. The packing diagram of (I), viewed down the c axis, showing the intermolecular hydrogen bonds (dashed lines).
2-[(5,7-Dibromoquinolin-8-yl)oxy]-N-(2-methoxyphenyl)acetamide top
Crystal data top
C18H14Br2N2O3F(000) = 920
Mr = 466.13Dx = 1.829 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4165 reflections
a = 8.7570 (18) Åθ = 1.8–27.9°
b = 8.7279 (17) ŵ = 4.81 mm−1
c = 22.372 (5) ÅT = 293 K
β = 98.04 (3)°Column, colourless
V = 1693.1 (6) Å30.06 × 0.02 × 0.02 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer		4027 independent reflections
Radiation source: fine-focus sealed tube3316 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.057
phi and ω scansθmax = 27.9°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −11→11
Tmin = 0.761, Tmax = 0.910k = −11→8
12864 measured reflectionsl = −29→28
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093H 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 parametersΔρmax = 0.83 e Å−3
1 restraintΔρmin = −0.71 e Å−3
Crystal data top
C18H14Br2N2O3V = 1693.1 (6) Å3
Mr = 466.13Z = 4
Monoclinic, P21/nMo Kα radiation
a = 8.7570 (18) ŵ = 4.81 mm−1
b = 8.7279 (17) ÅT = 293 K
c = 22.372 (5) Å0.06 × 0.02 × 0.02 mm
β = 98.04 (3)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		4027 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3316 reflections with I > 2σ(I)
Tmin = 0.761, Tmax = 0.910Rint = 0.057
12864 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0441 restraint
wR(F2) = 0.093H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.83 e Å−3
4027 reflectionsΔρmin = −0.71 e Å−3
231 parameters
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
xyzUiso*/Ueq
Br10.77254 (3)0.41089 (3)1.064695 (11)0.01979 (6)
Br20.16180 (3)0.18905 (3)1.014627 (12)0.02468 (7)
O10.81081 (18)0.22709 (18)0.94999 (7)0.0173 (4)
O21.0293 (2)0.39129 (19)0.84558 (8)0.0241 (4)
O30.8399 (2)−0.13107 (19)0.82222 (8)0.0262 (5)
N20.9123 (2)0.1556 (2)0.84366 (9)0.0171 (5)
N10.5971 (2)0.0662 (2)0.87776 (9)0.0190 (5)
C10.6236 (3)0.2953 (3)1.01398 (11)0.0171 (5)
C20.4727 (3)0.2851 (3)1.02927 (11)0.0180 (5)
H20.44740.33651.06300.022*
C30.3646 (3)0.1998 (3)0.99438 (11)0.0189 (6)
C40.3988 (3)0.1219 (3)0.94234 (11)0.0168 (5)
C50.2943 (3)0.0290 (3)0.90434 (11)0.0203 (6)
H50.19410.01500.91270.024*
C60.3416 (3)−0.0401 (3)0.85523 (12)0.0222 (6)
H60.2736−0.10050.82970.027*
C70.4956 (3)−0.0190 (3)0.84358 (11)0.0185 (6)
H70.5262−0.06760.81020.022*
C80.5505 (3)0.1348 (3)0.92702 (11)0.0167 (5)
C90.6633 (3)0.2237 (3)0.96423 (10)0.0144 (5)
C100.8431 (3)0.3518 (3)0.91172 (11)0.0199 (6)
H10A0.89760.43170.93620.024*
H10B0.74670.39460.89200.024*
C110.9396 (3)0.3002 (3)0.86413 (11)0.0167 (5)
C120.9771 (3)0.0828 (3)0.79679 (11)0.0171 (6)
C131.0774 (3)0.1524 (3)0.76220 (11)0.0219 (6)
H131.10710.25360.76970.026*
C141.1340 (3)0.0712 (3)0.71627 (12)0.0267 (7)
H141.20120.11880.69340.032*
C151.0912 (3)−0.0787 (3)0.70449 (12)0.0270 (7)
H151.1279−0.13170.67330.032*
C160.9923 (3)−0.1508 (3)0.73961 (12)0.0244 (6)
H160.9645−0.25260.73220.029*
C170.9358 (3)−0.0713 (3)0.78527 (11)0.0194 (6)
C180.8150 (3)−0.2923 (3)0.82018 (13)0.0284 (7)
H18A0.7705−0.32160.78010.043*
H18B0.7460−0.31980.84820.043*
H18C0.9116−0.34430.83080.043*
H2A0.8405 (13)0.106 (2)0.8612 (8)0.032 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.02090 (11)0.02052 (12)0.01835 (12)−0.00516 (10)0.00418 (10)−0.00258 (10)
Br20.01560 (11)0.02843 (13)0.03130 (14)−0.00014 (10)0.00784 (10)0.00388 (11)
O10.0136 (7)0.0182 (8)0.0208 (8)−0.0006 (7)0.0048 (7)0.0022 (7)
O20.0284 (9)0.0165 (8)0.0304 (10)−0.0091 (7)0.0149 (8)−0.0046 (7)
O30.0305 (9)0.0132 (8)0.0377 (10)−0.0036 (7)0.0139 (8)−0.0035 (8)
N20.0194 (9)0.0132 (9)0.0200 (10)0.0007 (8)0.0076 (8)0.0011 (8)
N10.0197 (10)0.0200 (10)0.0168 (10)0.0022 (8)0.0012 (9)0.0018 (8)
C10.0177 (11)0.0161 (11)0.0175 (12)0.0000 (9)0.0019 (9)0.0037 (9)
C20.0178 (11)0.0173 (11)0.0209 (12)0.0003 (9)0.0096 (10)0.0026 (10)
C30.0159 (11)0.0180 (11)0.0232 (12)0.0030 (9)0.0044 (10)0.0098 (10)
C40.0151 (10)0.0173 (11)0.0172 (12)0.0031 (9)−0.0006 (9)0.0085 (10)
C50.0160 (11)0.0179 (11)0.0261 (13)−0.0019 (10)0.0000 (10)0.0044 (10)
C60.0220 (12)0.0176 (12)0.0250 (13)−0.0035 (10)−0.0038 (11)0.0029 (10)
C70.0252 (12)0.0149 (11)0.0143 (11)−0.0027 (10)−0.0008 (10)−0.0010 (10)
C80.0202 (11)0.0138 (10)0.0161 (11)0.0007 (9)0.0025 (10)0.0048 (9)
C90.0117 (10)0.0141 (11)0.0175 (11)0.0006 (9)0.0030 (9)0.0035 (9)
C100.0242 (12)0.0127 (11)0.0247 (12)−0.0028 (10)0.0099 (10)−0.0012 (10)
C110.0152 (10)0.0158 (11)0.0191 (12)0.0012 (9)0.0024 (9)0.0012 (10)
C120.0200 (11)0.0160 (11)0.0138 (11)0.0025 (9)−0.0023 (10)0.0001 (9)
C130.0245 (12)0.0184 (12)0.0230 (13)0.0010 (10)0.0046 (11)0.0030 (10)
C140.0328 (14)0.0299 (14)0.0193 (13)0.0003 (12)0.0105 (11)0.0010 (11)
C150.0327 (14)0.0300 (14)0.0184 (13)0.0084 (12)0.0040 (11)−0.0057 (11)
C160.0288 (13)0.0183 (12)0.0261 (13)0.0028 (11)0.0031 (11)−0.0082 (11)
C170.0188 (11)0.0197 (12)0.0188 (12)0.0018 (10)−0.0009 (10)−0.0010 (10)
C180.0332 (14)0.0164 (12)0.0357 (15)−0.0043 (11)0.0055 (13)−0.0017 (11)
Geometric parameters (Å, º) top
Br1—C11.895 (2)C6—C71.420 (4)
Br2—C31.896 (2)C6—H60.9300
O1—C91.374 (3)C7—H70.9300
O1—C101.437 (3)C8—C91.429 (3)
O2—C111.230 (3)C10—C111.518 (3)
O3—C171.362 (3)C10—H10A0.9700
O3—C181.424 (3)C10—H10B0.9700
N2—C111.352 (3)C12—C131.389 (4)
N2—C121.411 (3)C12—C171.407 (3)
N2—H2A0.898 (9)C13—C141.395 (4)
N1—C71.318 (3)C13—H130.9300
N1—C81.366 (3)C14—C151.376 (4)
C1—C91.363 (3)C14—H140.9300
C1—C21.414 (3)C15—C161.398 (4)
C2—C31.361 (3)C15—H150.9300
C2—H20.9300C16—C171.383 (4)
C3—C41.416 (3)C16—H160.9300
C4—C51.415 (3)C18—H18A0.9600
C4—C81.421 (3)C18—H18B0.9600
C5—C61.368 (4)C18—H18C0.9600
C5—H50.9300
C9—O1—C10115.11 (17)O1—C10—C11111.60 (19)
C17—O3—C18117.6 (2)O1—C10—H10A109.3
C11—N2—C12127.0 (2)C11—C10—H10A109.3
C11—N2—H2A113.8 (14)O1—C10—H10B109.3
C12—N2—H2A119.1 (14)C11—C10—H10B109.3
C7—N1—C8117.5 (2)H10A—C10—H10B108.0
C9—C1—C2121.5 (2)O2—C11—N2125.5 (2)
C9—C1—Br1120.03 (18)O2—C11—C10119.3 (2)
C2—C1—Br1118.47 (18)N2—C11—C10115.2 (2)
C3—C2—C1119.6 (2)C13—C12—C17118.8 (2)
C3—C2—H2120.2C13—C12—N2124.7 (2)
C1—C2—H2120.2C17—C12—N2116.5 (2)
C2—C3—C4121.6 (2)C12—C13—C14120.4 (2)
C2—C3—Br2119.32 (19)C12—C13—H13119.8
C4—C3—Br2119.06 (17)C14—C13—H13119.8
C5—C4—C3125.1 (2)C15—C14—C13120.6 (3)
C5—C4—C8116.7 (2)C15—C14—H14119.7
C3—C4—C8118.2 (2)C13—C14—H14119.7
C6—C5—C4119.5 (2)C14—C15—C16119.6 (3)
C6—C5—H5120.3C14—C15—H15120.2
C4—C5—H5120.3C16—C15—H15120.2
C5—C6—C7119.5 (2)C17—C16—C15120.2 (2)
C5—C6—H6120.3C17—C16—H16119.9
C7—C6—H6120.3C15—C16—H16119.9
N1—C7—C6123.2 (2)O3—C17—C16124.8 (2)
N1—C7—H7118.4O3—C17—C12114.8 (2)
C6—C7—H7118.4C16—C17—C12120.4 (2)
N1—C8—C4123.7 (2)O3—C18—H18A109.5
N1—C8—C9116.6 (2)O3—C18—H18B109.5
C4—C8—C9119.7 (2)H18A—C18—H18B109.5
C1—C9—O1122.3 (2)O3—C18—H18C109.5
C1—C9—C8119.4 (2)H18A—C18—H18C109.5
O1—C9—C8118.2 (2)H18B—C18—H18C109.5
C9—C1—C2—C31.2 (4)N1—C8—C9—C1179.8 (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—O1176.6 (2)
C2—C3—C4—C5178.9 (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—C80.0 (3)C12—N2—C11—C10175.2 (2)
Br2—C3—C4—C8178.33 (17)O1—C10—C11—O2−149.5 (2)
C3—C4—C5—C6179.9 (2)O1—C10—C11—N233.5 (3)
C8—C4—C5—C6−1.2 (3)C11—N2—C12—C13−2.4 (4)
C4—C5—C6—C70.7 (4)C11—N2—C12—C17177.4 (2)
C8—N1—C7—C60.9 (3)C17—C12—C13—C141.0 (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—C150.1 (4)
C7—N1—C8—C9178.6 (2)C13—C14—C15—C16−1.1 (4)
C5—C4—C8—N11.6 (3)C14—C15—C16—C171.1 (4)
C3—C4—C8—N1−179.4 (2)C18—O3—C17—C1610.3 (3)
C5—C4—C8—C9−178.5 (2)C18—O3—C17—C12−169.3 (2)
C3—C4—C8—C90.5 (3)C15—C16—C17—O3−179.5 (2)
C2—C1—C9—O1−177.3 (2)C15—C16—C17—C120.0 (4)
Br1—C1—C9—O12.3 (3)C13—C12—C17—O3178.5 (2)
C2—C1—C9—C8−0.7 (3)N2—C12—C17—O3−1.3 (3)
Br1—C1—C9—C8178.94 (17)C13—C12—C17—C16−1.1 (4)
C10—O1—C9—C1−90.4 (3)N2—C12—C17—C16179.1 (2)
C10—O1—C9—C892.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···N10.90 (1)2.24 (1)3.065 (3)153 (1)
C18—H18C···O2i0.962.533.342 (3)142
Symmetry code: (i) x, y−1, z.

Experimental details

Crystal data
Chemical formulaC18H14Br2N2O3
Mr466.13
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)8.7570 (18), 8.7279 (17), 22.372 (5)
β (°) 98.04 (3)
V (Å3)1693.1 (6)
Z4
Radiation typeMo Kα
µ (mm−1)4.81
Crystal size (mm)0.06 × 0.02 × 0.02
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.761, 0.910
No. of measured, independent and
observed [I > 2σ(I)] reflections		12864, 4027, 3316
Rint0.057
(sin θ/λ)max (Å−1)0.658
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.093, 1.06
No. of reflections4027
No. of parameters231
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.83, −0.71

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···N10.898 (9)2.240 (10)3.065 (3)152.5 (14)
C18—H18C···O2i0.962.533.342 (3)142.4
Symmetry code: (i) x, y−1, z.
 

Acknowledgements

This work was supported by the National Natural Science Foundation of China (No. 20971076), the Outstanding Adult–young Scientific Research Encouraging Foundation of Shandong Province, China (No. 2008BS0901). The authors acknowledge X.-F. Tang's help with this paper.

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CSD CrossRef Web of Science Google Scholar
 First citationBratzel, M. P., Aaron, J. J., Winefordner, J. D., Schulman, S. G. & Gershon, H. (1972). Anal. Chem. 44, 1240–1245.  CrossRef CAS Web of Science Google Scholar
 First citationBruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationLiu, J.-F., Tang, X.-F. & Wen, Y.-H. (2007). Acta Cryst. E63, o4458.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationPatel, A. K. & Patel, V. M. (1999). Synth. React. Inorg. Met. Org. Chem. 29, 193–197.  CrossRef CAS Google Scholar
 First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 66| Part 12| December 2010| Page o3294
https://doi.org/10.1107/S1600536810048312
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