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ISSN: 2056-9890

(4-Bromo­phen­yl)(1H-indol-7-yl)methanone

aDepartment of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland, and bDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India
*Correspondence e-mail: mkubicki@amu.edu.pl

(Received 1 October 2009; accepted 7 October 2009; online 31 October 2009)

In the crystal, the mol­ecules of the title compound, C15H10BrNO, are connected into centrosymmetric dimers by pairs of N—H⋯O hydrogen bonds. The dihedral angle between the planes of indole ring system and benzene ring is 50.13 (5)°. The indole plane is significantly less twisted from the plane of the central C—C(=O)—C bridge than the benzene plane [dihedral angles = 15.51 (3) and 40.13 (7)°, respectively]. The bond angles within the benzene ring show an approximately additive effect of the influence of both substituents.

Related literature

For applications of indoles, see: Murphy et al. (1997[Murphy, J. A., Scott, K. A., Sinclair, R. S. & Lewis, N. (1997). Tetrahedron Lett. 38, 7295-7298.]); Gupta et al. (1982[Gupta, A. K. S., Srivastava, N. & Gupta, A. A. (1982). Curr. Sci. 51, 1100-1103.]); Al-Soud et al. (2004[Al-Soud, Y. A., Al-Dweri, M. N. & Al-Masoudi, N. A. (2004). Farmaco, 59, 775-783.]); Shigenaga et al. (1993[Shigenaga, S., Manabe, T., Matsuda, H., Fujii, T., Hiroi, J. & &Matsuo, M. (1993). Chem. Pharm. Bull. 41, 1589-1595.]); Butera et al. (2001[Butera, J. A., Antane, S. A., Hirth, B., Lennox, J. R., Sheldon, J. H., Norton, N. W., Warga, D. & Argentieri, T. M. (2001). Bioorg. Med. Chem. Lett. 11, 2093-2097.]). For synthethic procedures, see: Robinson (1982[Robinson, B. (1982). The Fischer Indole Synthesis. New York: John Wiley and Sons.]); Walsh et al. (1984[Walsh, D. A., Moran, H. W., Shamblee, D. A., Uwaydha, I. M., Welstead, W. J., Sancilio, L. F. & Dannenburg, W. N. (1984). J. Med. Chem. 27, 1379-1388.]). For related crystal structures of 7-pyridyl­indoles, see: Mudadu et al. (2006[Mudadu, M. S., Singh, A. & Thummel, R. P. (2006). J. Org. Chem. 71, 7611-7617.]). For the influence of the substituent on the geometry of the phenyl ring, see: Domenicano (1988[Domenicano, A. (1988). In Stereochemical Application of Gas-phase Electron Diffraction, Part B, Structural Information for Selected Classes of Compounds, edited by I. Hargittai & M. Hargittai, pp. 281-324. Weinheim: VCH.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data
  • C15H10BrNO

  • Mr = 300.15

  • Monoclinic, P 21 /n

  • a = 11.3241 (4) Å

  • b = 7.4651 (3) Å

  • c = 14.9579 (5) Å

  • β = 103.100 (4)°

  • V = 1231.57 (8) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 3.32 mm−1

  • T = 291 K

  • 0.4 × 0.2 × 0.15 mm

Data collection
  • Oxford Diffraction Xcalibur (Sapphire2, large Be window) diffractometer

  • Absorption correction: multi-scan (CrysAlis Pro; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis Pro. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.26, Tmax = 0.60

  • 25357 measured reflections

  • 2558 independent reflections

  • 1864 reflections with I > 2σ(I)

  • Rint = 0.036

Refinement
  • R[F2 > 2σ(F2)] = 0.024

  • wR(F2) = 0.063

  • S = 1.06

  • 2558 reflections

  • 174 parameters

  • H-atom parameters constrained

  • Δρmax = 0.34 e Å−3

  • Δρmin = −0.29 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O10i 0.86 2.14 2.935 (2) 153
Symmetry code: (i) -x+1, -y, -z+2.

Data collection: CrysAlis Pro (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis Pro. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis Pro; data reduction: CrysAlis Pro; program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: Stereochemical Workstation Operation Manual (Siemens, 1989[Siemens (1989). Stereochemical Workstation Operation Manual. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

The synthesis of indole derivatives has long been a topic of fundamental interest to organic and medicinal chemists (Murphy et al., 1997). Indole derivatives are important pharmacologically, possessing anti-allergic (Shigenaga et al., 1993), central-nervous-system depressant (Sen Gupta et al., 1982), muscle relaxant (Butera et al.,2001), and anti-cancer (Al-Soud et al.,2004) properties. The Fischer indole synthesis is the most widely used method for the preparation of indole derivatives (e.g., Robinson, 1982). The title compound (I) is an intermediate for preparation of bromofenac, which is used as analgesic.

There are only few crystal structures of 7-substituted indoles in the Cambridge Crystallographic Database (Allen, 2002). Recently, the crystal structures of three 7-pyridylindoles (Mudadu et al., 2006) have been reported.

The conformation of the molecule I can be described by the mutual orientation of the three approximately planar fragments (Fig. 1): indole system (maximum deviation from the least-squares plane of 0.0142 (7) Å), phenyl ring (maximum deviation 0.0145 (13) Å), and the central C—C(=O)—C bridge (0.0040 (16) Å). The dihedral angle between the terminal planes, of indole and phenyl fragments, is 50.13 (5)°, while it can be noted that the indole plane is less inclined with respect to the central bridge plane (15.51 (3)°) than is the phenyl one (40.13 (7)°). The geometry of the phenyl ring is affected by the presence of substituents; using the values given by Domenicano (1988) and obtained form the search of the CSD (Allen, 2002), it might be shown that the overall influence on the bond angles pattern is close to additivity of separate effects of both Br and COAr substituents.

In the crystal structure the molecules of (I) are connected into the centrosymmetric, hydrogen bonded pairs - R22(12) motifs - by means of relatively strong and linear N—H···O hydrogen bonds (Fig. 2). These dimers are packed by means of van der Waals and weak C—H···π interactions.

Related literature top

For applications of indoles, see: Murphy et al. (1997); Gupta et al. (1982); Al-Soud et al. (2004); Shigenaga et al. (1993); Butera et al. (2001). For synthethic procedures, see: Robinson (1982); Walsh et al. (1984). For related crystal structures of 7-pyridylindoles, see: Mudadu et al. (2006). For the influence of the substituent on the geometry of the phenyl ring, see: Domenicano (1988). For a description of the Cambridge Structural Database, see: Allen (2002).

Experimental top

A mixture of (4-bromophenyl)(2,3-dihydro-1H-indol-7-yl)methanone (2.4 g, 7.9 m mol) and activated manganese dioxide (2.2 g, 25 m mol) in 100 ml dichloromethane was refluxed for 18 h (Fig. 3). The contents were filtered and the organic layer was concentrated. The product formed (Walsh et al., 1984) was crystallized from tetrahydrofuran (m.p.: 435 – 437 K).

Refinement top

Hydrogen atoms were put in the idealized positions, and refined as riding model.

Structure description top

The synthesis of indole derivatives has long been a topic of fundamental interest to organic and medicinal chemists (Murphy et al., 1997). Indole derivatives are important pharmacologically, possessing anti-allergic (Shigenaga et al., 1993), central-nervous-system depressant (Sen Gupta et al., 1982), muscle relaxant (Butera et al.,2001), and anti-cancer (Al-Soud et al.,2004) properties. The Fischer indole synthesis is the most widely used method for the preparation of indole derivatives (e.g., Robinson, 1982). The title compound (I) is an intermediate for preparation of bromofenac, which is used as analgesic.

There are only few crystal structures of 7-substituted indoles in the Cambridge Crystallographic Database (Allen, 2002). Recently, the crystal structures of three 7-pyridylindoles (Mudadu et al., 2006) have been reported.

The conformation of the molecule I can be described by the mutual orientation of the three approximately planar fragments (Fig. 1): indole system (maximum deviation from the least-squares plane of 0.0142 (7) Å), phenyl ring (maximum deviation 0.0145 (13) Å), and the central C—C(=O)—C bridge (0.0040 (16) Å). The dihedral angle between the terminal planes, of indole and phenyl fragments, is 50.13 (5)°, while it can be noted that the indole plane is less inclined with respect to the central bridge plane (15.51 (3)°) than is the phenyl one (40.13 (7)°). The geometry of the phenyl ring is affected by the presence of substituents; using the values given by Domenicano (1988) and obtained form the search of the CSD (Allen, 2002), it might be shown that the overall influence on the bond angles pattern is close to additivity of separate effects of both Br and COAr substituents.

In the crystal structure the molecules of (I) are connected into the centrosymmetric, hydrogen bonded pairs - R22(12) motifs - by means of relatively strong and linear N—H···O hydrogen bonds (Fig. 2). These dimers are packed by means of van der Waals and weak C—H···π interactions.

For applications of indoles, see: Murphy et al. (1997); Gupta et al. (1982); Al-Soud et al. (2004); Shigenaga et al. (1993); Butera et al. (2001). For synthethic procedures, see: Robinson (1982); Walsh et al. (1984). For related crystal structures of 7-pyridylindoles, see: Mudadu et al. (2006). For the influence of the substituent on the geometry of the phenyl ring, see: Domenicano (1988). For a description of the Cambridge Structural Database, see: Allen (2002).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Stereochemical Workstation Operation Manual (Siemens, 1989); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Anisotropic ellipsoid representation of the compound I together with atom labelling scheme. The ellipsoids are drawn at 50% probability level, hydrogen atoms are depicted as spheres with arbitrary radii.
[Figure 2] Fig. 2. The hydrogen bonded dimer of molecules of I. Hydrogen bonds are shown as dashed lines. Symmetry code: (i) 1 - x,-y,2 - z.
[Figure 3] Fig. 3. The preparation of the title compound.
(4-Bromophenyl)(1H-indol-7-yl)methanone top
Crystal data top
C15H10BrNOF(000) = 600
Mr = 300.15Dx = 1.619 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 12183 reflections
a = 11.3241 (4) Åθ = 2.0–26.8°
b = 7.4651 (3) ŵ = 3.32 mm1
c = 14.9579 (5) ÅT = 291 K
β = 103.100 (4)°Block, colourless
V = 1231.57 (8) Å30.4 × 0.2 × 0.15 mm
Z = 4
Data collection top
Oxford Diffraction Xcalibur (Sapphire2, large Be window)
diffractometer
2558 independent reflections
Radiation source: Enhance (Mo) X-ray Source1864 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
Detector resolution: 8.1929 pixels mm-1θmax = 26.8°, θmin = 2.1°
ω scansh = 1314
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
k = 99
Tmin = 0.26, Tmax = 0.60l = 1818
25357 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.024H-atom parameters constrained
wR(F2) = 0.063 w = 1/[σ2(Fo2) + (0.035P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
2558 reflectionsΔρmax = 0.34 e Å3
174 parametersΔρmin = 0.29 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0139 (9)
Crystal data top
C15H10BrNOV = 1231.57 (8) Å3
Mr = 300.15Z = 4
Monoclinic, P21/nMo Kα radiation
a = 11.3241 (4) ŵ = 3.32 mm1
b = 7.4651 (3) ÅT = 291 K
c = 14.9579 (5) Å0.4 × 0.2 × 0.15 mm
β = 103.100 (4)°
Data collection top
Oxford Diffraction Xcalibur (Sapphire2, large Be window)
diffractometer
2558 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
1864 reflections with I > 2σ(I)
Tmin = 0.26, Tmax = 0.60Rint = 0.036
25357 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0240 restraints
wR(F2) = 0.063H-atom parameters constrained
S = 1.06Δρmax = 0.34 e Å3
2558 reflectionsΔρmin = 0.29 e Å3
174 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
N10.28642 (14)0.0239 (2)0.94540 (10)0.0386 (4)
H10.36010.02740.97680.053 (6)*
C20.18656 (19)0.0579 (3)0.97896 (14)0.0459 (5)
H20.18760.08721.03960.043 (5)*
C30.08506 (18)0.0424 (3)0.91063 (14)0.0449 (5)
H30.00560.06040.91570.053 (6)*
C40.12356 (15)0.0064 (3)0.83002 (13)0.0344 (4)
C50.25153 (15)0.0167 (3)0.85411 (11)0.0315 (4)
C60.32088 (15)0.0562 (2)0.78996 (12)0.0314 (4)
C70.25687 (16)0.0912 (2)0.70024 (12)0.0353 (4)
H70.29950.12000.65590.035 (5)*
C80.13073 (17)0.0839 (2)0.67577 (13)0.0400 (5)
H80.09080.10830.61550.046 (6)*
C90.06422 (17)0.0413 (2)0.73904 (14)0.0387 (5)
H90.01990.03570.72150.053 (6)*
C100.45391 (16)0.0642 (2)0.81808 (12)0.0372 (4)
O100.50404 (12)0.0723 (2)0.90015 (9)0.0593 (5)
C110.53044 (15)0.0650 (2)0.74900 (12)0.0322 (4)
C120.50633 (16)0.0445 (2)0.67135 (13)0.0352 (4)
H120.43870.11880.66050.041 (6)*
C130.58143 (17)0.0438 (2)0.61058 (12)0.0371 (5)
H130.56560.11890.55960.035 (5)*
C140.68042 (16)0.0694 (3)0.62617 (12)0.0363 (4)
Br140.779765 (18)0.07710 (3)0.539996 (14)0.05633 (12)
C150.70737 (16)0.1777 (3)0.70285 (12)0.0389 (5)
H150.77460.25290.71290.051 (6)*
C160.63296 (15)0.1728 (3)0.76455 (12)0.0366 (4)
H160.65190.24280.81730.036 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0302 (9)0.0511 (11)0.0332 (8)0.0010 (8)0.0045 (7)0.0004 (7)
C20.0452 (12)0.0568 (14)0.0390 (10)0.0020 (10)0.0167 (9)0.0002 (10)
C30.0309 (11)0.0563 (14)0.0504 (12)0.0031 (10)0.0157 (9)0.0039 (10)
C40.0294 (10)0.0291 (10)0.0446 (10)0.0011 (8)0.0080 (8)0.0049 (9)
C50.0303 (10)0.0275 (10)0.0350 (10)0.0002 (8)0.0034 (7)0.0032 (8)
C60.0268 (9)0.0303 (11)0.0353 (9)0.0016 (8)0.0032 (7)0.0017 (8)
C70.0326 (10)0.0355 (11)0.0367 (10)0.0008 (9)0.0057 (8)0.0033 (8)
C80.0348 (11)0.0415 (12)0.0387 (10)0.0027 (9)0.0020 (8)0.0028 (9)
C90.0248 (10)0.0376 (12)0.0502 (11)0.0015 (8)0.0011 (8)0.0024 (9)
C100.0320 (10)0.0415 (12)0.0358 (10)0.0035 (9)0.0028 (8)0.0037 (9)
O100.0339 (8)0.1051 (14)0.0347 (7)0.0108 (8)0.0010 (6)0.0059 (8)
C110.0240 (9)0.0341 (10)0.0353 (9)0.0015 (8)0.0004 (7)0.0034 (8)
C120.0283 (10)0.0321 (12)0.0410 (10)0.0031 (8)0.0007 (8)0.0021 (8)
C130.0354 (11)0.0350 (12)0.0363 (10)0.0059 (9)0.0015 (8)0.0007 (9)
C140.0283 (10)0.0428 (12)0.0366 (9)0.0071 (9)0.0047 (8)0.0086 (9)
Br140.04658 (16)0.0801 (2)0.04560 (15)0.00255 (12)0.01738 (10)0.00603 (11)
C150.0268 (10)0.0424 (12)0.0454 (11)0.0057 (9)0.0034 (8)0.0012 (9)
C160.0284 (10)0.0402 (12)0.0386 (10)0.0011 (9)0.0020 (8)0.0045 (9)
Geometric parameters (Å, º) top
N1—C21.361 (3)C8—H80.9300
N1—C51.367 (2)C9—H90.9300
N1—H10.8600C10—O101.232 (2)
C2—C31.359 (3)C10—C111.492 (2)
C2—H20.9300C11—C161.388 (2)
C3—C41.419 (3)C11—C121.395 (3)
C3—H30.9300C12—C131.378 (3)
C4—C91.399 (3)C12—H120.9300
C4—C51.414 (2)C13—C141.381 (3)
C5—C61.402 (2)C13—H130.9300
C6—C71.398 (2)C14—C151.380 (3)
C6—C101.471 (2)C14—Br141.8941 (18)
C7—C81.393 (2)C15—C161.384 (2)
C7—H70.9300C15—H150.9300
C8—C91.374 (3)C16—H160.9300
C2—N1—C5109.49 (16)C8—C9—C4119.72 (17)
C2—N1—H1125.3C8—C9—H9120.1
C5—N1—H1125.3C4—C9—H9120.1
C3—C2—N1109.79 (18)O10—C10—C6119.87 (17)
C3—C2—H2125.1O10—C10—C11118.77 (17)
N1—C2—H2125.1C6—C10—C11121.36 (15)
C2—C3—C4106.88 (17)C16—C11—C12118.51 (17)
C2—C3—H3126.6C16—C11—C10118.77 (16)
C4—C3—H3126.6C12—C11—C10122.66 (16)
C9—C4—C5118.45 (17)C13—C12—C11120.89 (17)
C9—C4—C3134.58 (18)C13—C12—H12119.6
C5—C4—C3106.97 (16)C11—C12—H12119.6
N1—C5—C6130.57 (15)C12—C13—C14119.29 (17)
N1—C5—C4106.86 (16)C12—C13—H13120.4
C6—C5—C4122.53 (15)C14—C13—H13120.4
C7—C6—C5116.57 (16)C15—C14—C13121.14 (17)
C7—C6—C10122.80 (16)C15—C14—Br14119.62 (14)
C5—C6—C10120.61 (15)C13—C14—Br14119.24 (14)
C8—C7—C6121.52 (17)C14—C15—C16119.04 (18)
C8—C7—H7119.2C14—C15—H15120.5
C6—C7—H7119.2C16—C15—H15120.5
C9—C8—C7121.18 (17)C15—C16—C11121.07 (18)
C9—C8—H8119.4C15—C16—H16119.5
C7—C8—H8119.4C11—C16—H16119.5
C5—N1—C2—C30.7 (2)C3—C4—C9—C8179.0 (2)
N1—C2—C3—C40.8 (2)C7—C6—C10—O10163.69 (18)
C2—C3—C4—C9179.9 (2)C5—C6—C10—O1014.7 (3)
C2—C3—C4—C50.6 (2)C7—C6—C10—C1115.5 (3)
C2—N1—C5—C6178.08 (19)C5—C6—C10—C11166.12 (17)
C2—N1—C5—C40.3 (2)O10—C10—C11—C1637.9 (3)
C9—C4—C5—N1179.61 (17)C6—C10—C11—C16141.34 (18)
C3—C4—C5—N10.2 (2)O10—C10—C11—C12139.08 (19)
C9—C4—C5—C61.6 (3)C6—C10—C11—C1241.7 (3)
C3—C4—C5—C6177.79 (17)C16—C11—C12—C131.0 (3)
N1—C5—C6—C7179.52 (18)C10—C11—C12—C13177.97 (16)
C4—C5—C6—C72.0 (3)C11—C12—C13—C141.2 (3)
N1—C5—C6—C102.0 (3)C12—C13—C14—C152.0 (3)
C4—C5—C6—C10179.52 (18)C12—C13—C14—Br14177.47 (13)
C5—C6—C7—C81.1 (3)C13—C14—C15—C160.4 (3)
C10—C6—C7—C8179.52 (17)Br14—C14—C15—C16179.00 (14)
C6—C7—C8—C90.2 (3)C14—C15—C16—C111.9 (3)
C7—C8—C9—C40.7 (3)C12—C11—C16—C152.5 (3)
C5—C4—C9—C80.2 (3)C10—C11—C16—C15179.66 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10i0.862.142.935 (2)153
Symmetry code: (i) x+1, y, z+2.

Experimental details

Crystal data
Chemical formulaC15H10BrNO
Mr300.15
Crystal system, space groupMonoclinic, P21/n
Temperature (K)291
a, b, c (Å)11.3241 (4), 7.4651 (3), 14.9579 (5)
β (°) 103.100 (4)
V3)1231.57 (8)
Z4
Radiation typeMo Kα
µ (mm1)3.32
Crystal size (mm)0.4 × 0.2 × 0.15
Data collection
DiffractometerOxford Diffraction Xcalibur (Sapphire2, large Be window)
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
Tmin, Tmax0.26, 0.60
No. of measured, independent and
observed [I > 2σ(I)] reflections
25357, 2558, 1864
Rint0.036
(sin θ/λ)max1)0.635
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.024, 0.063, 1.06
No. of reflections2558
No. of parameters174
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.34, 0.29

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), Stereochemical Workstation Operation Manual (Siemens, 1989).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10i0.862.142.935 (2)153.3
Symmetry code: (i) x+1, y, z+2.
 

Acknowledgements

CSC thanks the University of Mysore for research facilities.

References

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