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ISSN: 2056-9890

N-Cyclo­hexyl-2-(5-meth­­oxy-1H-indol-3-yl)-2-oxoacetamide

aSchool of Pharmacy, Tianjin Medical University, Tianjin 300070, People's Republic of China, bRoom of Pharmacognosy, Medical College of Chinese People's Armed Police Forces, Tianjin 300162, People's Republic of China, and cTianjin Key Laboratory for Biomarkers of Occupational and Environmental Hazards, Tianjin 300162, People's Republic of China
*Correspondence e-mail: tjch2010@yahoo.cn

(Received 21 December 2010; accepted 29 December 2010; online 8 January 2011)

In the title compound, C17H20N2O3, the cyclo­hexane ring adopts a chair conformation. In the crystal, inter­molecular N—H⋯O hydrogen bonds link the mol­ecules into layers parallel to the ac plane.

Related literature

For the biological activity of indole derivatives, see: Souli et al. (2008[Souli, E., Machluf, M., Morgenstern, A., Sabo, E. & Yannai, S. (2008). Food Chem. Toxicol. 46, 863-870.]); Chai et al. (2006[Chai, H. F., Zhao, Y. F., Zhao, C. S. & Gong, P. (2006). Bioorg. Med. Chem. 14, 911-917.]); Radwan et al. (2007[Radwan, M. A. A., Ragab, E. A., Sabry, N. M. & El-Shenawy, S. M. (2007). Bioorg. Med. Chem. 15, 3832-3841.]); Karthikeyan et al., (2009[Karthikeyan, S. V., Perumal, S., Shetty, K. A., Yogeeswari, P. & Sriram, D. (2009). Bioorg. Med. Chem. Lett. 19, 3006-3009.]). For details of the synthesis, see: Bacher et al. (2001[Bacher, G., Nickel, B., Emig, P., Vanhoefer, U., Seeber, S., Shandra, A., Klenner, T. & Becker, T. (2001). Cancer Res. 61, 392-399.]). For similar structures, see: Feng et al. (2008[Feng, M., Zhao, M., Zhang, J., Yang, Z. & Chen, H. (2008). Acta Cryst. E64, o2339.]); Sonar et al. (2006[Sonar, V. N., Parkin, S. & Crooks, P. A. (2006). Acta Cryst. E62, o3744-o3746.]).

[Scheme 1]

Experimental

Crystal data
  • C17H20N2O3

  • Mr = 300.35

  • Monoclinic, P 21

  • a = 5.083 (3) Å

  • b = 27.336 (13) Å

  • c = 5.220 (3) Å

  • β = 91.977 (12)°

  • V = 724.9 (6) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 113 K

  • 0.20 × 0.18 × 0.10 mm

Data collection
  • Rigaku Saturn CCD area-detector diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005[Rigaku. (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.981, Tmax = 0.991

  • 7342 measured reflections

  • 1764 independent reflections

  • 1569 reflections with I > 2σ(I)

  • Rint = 0.042

Refinement
  • R[F2 > 2σ(F2)] = 0.035

  • wR(F2) = 0.076

  • S = 1.02

  • 1764 reflections

  • 208 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.23 e Å−3

  • Δρmin = −0.18 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O2i 0.96 (3) 1.90 (3) 2.840 (2) 164 (3)
N2—H2⋯O3ii 0.88 (3) 2.09 (3) 2.926 (3) 160 (3)
Symmetry codes: (i) x+1, y, z-1; (ii) x-1, y, z.

Data collection: CrystalClear (Rigaku, 2005[Rigaku. (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: XP in SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Indole and their derivatives are well known as substances exhibiting various biological activiies, such as anti-cancer (Souli et al., 2008), anti-viral (Chai et al., 2006), anti-tubercular (Karthikeyan et al., 2009) and anti-inflammatory (Radwan et al., 2007). In our search for new indole derivatives with improved activities, we have synthesized the title compound, (I). Here we report its crystal structure.

In (I) (Fig. 1), all bond lengths and angles are normal and in a good agreement with those reported previously (Feng et al., 2008; Sonar et al., 2006). The cyclohexane ring (C12—C17) adopts a chair conformation. In the crystal structure, intermolecular N—H···O hydrogen bonds (Table 1) link the molecules into layers parallel to the ac plane.

Related literature top

For the biological activity of indole derivatives, see: Souli et al. (2008); Chai et al. (2006); Radwan et al. (2007); Karthikeyan et al., (2009). For details of the synthesis, see: Bacher et al. (2001). For similar structures, see: Feng et al. (2008); Sonar et al. (2006).

Experimental top

The target compound was synthesized by two steps. Oxalyl chloride was added dropwise to a solution of 5-methoxy-indole in dry ether, the crude product 5-methoxyindol-3-yl-glyoxyl chloride, cyclohexylamine, two drops of triethylamine in dry dichloromethane. The reaction mixture was washed with water and dried over MgSO4 and concentrated in vacuo (Bacher et al., 2001). The residue was resolved in a methanol solution. Slow evaporation over two weeks at room temperature gave light-yellow crystals suitable for X-ray analysis.

Refinement top

C-bound H atoms were geometrically positioned (C—H = 0.95–1.00 Å), and refined as riding, with Uiso(H) = 1.2-1.5 Ueq(C). Amino H atoms were located on a difference map and refined isotropically.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. View of the title compound, with displacement ellipsoids drawn at the 40% probability level.
N-Cyclohexyl-2-(5-methoxy-1H-indol-3-yl)-2-oxoacetamide top
Crystal data top
C17H20N2O3F(000) = 320
Mr = 300.35Dx = 1.376 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 2636 reflections
a = 5.083 (3) Åθ = 1.5–27.9°
b = 27.336 (13) ŵ = 0.10 mm1
c = 5.220 (3) ÅT = 113 K
β = 91.977 (12)°Prism, colourless
V = 724.9 (6) Å30.20 × 0.18 × 0.10 mm
Z = 2
Data collection top
Rigaku Saturn CCD area-detector
diffractometer
1764 independent reflections
Radiation source: rotating anode1569 reflections with I > 2σ(I)
Multilayer monochromatorRint = 0.042
Detector resolution: 14.63 pixels mm-1θmax = 27.9°, θmin = 1.5°
ω and ϕ scansh = 66
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
k = 3631
Tmin = 0.981, Tmax = 0.991l = 66
7342 measured reflections
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)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0439P)2]
where P = (Fo2 + 2Fc2)/3
1764 reflections(Δ/σ)max = 0.003
208 parametersΔρmax = 0.23 e Å3
1 restraintΔρmin = 0.18 e Å3
Crystal data top
C17H20N2O3V = 724.9 (6) Å3
Mr = 300.35Z = 2
Monoclinic, P21Mo Kα radiation
a = 5.083 (3) ŵ = 0.10 mm1
b = 27.336 (13) ÅT = 113 K
c = 5.220 (3) Å0.20 × 0.18 × 0.10 mm
β = 91.977 (12)°
Data collection top
Rigaku Saturn CCD area-detector
diffractometer
1764 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
1569 reflections with I > 2σ(I)
Tmin = 0.981, Tmax = 0.991Rint = 0.042
7342 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0351 restraint
wR(F2) = 0.076H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.23 e Å3
1764 reflectionsΔρmin = 0.18 e Å3
208 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. Along with the meaningless absolute structure parameter value (and s.u. value) obtained from any refinement with Friedel pairs, as justification of the merging of Friedel-pair data.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.1844 (3)0.03318 (6)0.3071 (3)0.0242 (4)
O20.1506 (3)0.20016 (5)0.8241 (3)0.0181 (3)
O30.3519 (3)0.28545 (6)0.8311 (3)0.0209 (4)
N10.4663 (4)0.19176 (7)0.2050 (3)0.0175 (4)
N20.0791 (4)0.29907 (6)0.8997 (3)0.0167 (4)
C10.3621 (4)0.03287 (9)0.5127 (5)0.0241 (5)
H1A0.26270.03600.67610.036*
H1B0.46070.00210.51060.036*
H1C0.48510.06030.49270.036*
C20.0281 (4)0.07411 (8)0.2854 (4)0.0191 (5)
C30.1505 (4)0.07156 (8)0.0851 (4)0.0207 (5)
H30.15080.04350.02230.025*
C40.3242 (4)0.10905 (8)0.0430 (4)0.0185 (4)
H40.44460.10750.09200.022*
C50.3169 (4)0.14924 (7)0.2052 (4)0.0158 (4)
C60.3895 (4)0.22142 (8)0.3936 (4)0.0182 (4)
H60.46320.25260.43190.022*
C70.1850 (4)0.19958 (8)0.5251 (4)0.0147 (4)
C80.1372 (4)0.15268 (8)0.4031 (4)0.0153 (4)
C90.0386 (4)0.11418 (8)0.4453 (4)0.0170 (4)
H90.16030.11560.57920.020*
C100.0403 (4)0.22048 (7)0.7283 (4)0.0150 (4)
C110.1203 (4)0.27147 (7)0.8258 (4)0.0154 (4)
C120.0360 (4)0.35000 (7)0.9780 (4)0.0168 (4)
H120.10850.36360.87390.020*
C130.2834 (4)0.38039 (8)0.9209 (4)0.0187 (4)
H13A0.43020.36751.02080.022*
H13B0.33400.37770.73660.022*
C140.2356 (5)0.43413 (8)0.9899 (4)0.0194 (5)
H14A0.40000.45290.95870.023*
H14B0.09950.44780.87930.023*
C150.1453 (4)0.43918 (8)1.2721 (4)0.0184 (4)
H15A0.10480.47391.31060.022*
H15B0.28880.42871.38320.022*
C160.0984 (4)0.40803 (8)1.3293 (4)0.0205 (5)
H16A0.14860.41061.51370.025*
H16B0.24660.42061.23010.025*
C170.0493 (4)0.35425 (8)1.2602 (4)0.0185 (5)
H17A0.21230.33511.29340.022*
H17B0.08970.34081.36820.022*
H10.603 (6)0.2006 (11)0.090 (6)0.042 (8)*
H20.240 (5)0.2875 (10)0.891 (5)0.027 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0251 (8)0.0167 (8)0.0310 (9)0.0030 (7)0.0032 (7)0.0044 (7)
O20.0158 (7)0.0174 (8)0.0214 (8)0.0014 (6)0.0052 (6)0.0016 (6)
O30.0157 (7)0.0193 (8)0.0277 (9)0.0012 (6)0.0022 (6)0.0038 (6)
N10.0182 (9)0.0182 (9)0.0167 (9)0.0019 (7)0.0070 (7)0.0002 (7)
N20.0132 (9)0.0159 (9)0.0211 (10)0.0008 (7)0.0020 (7)0.0023 (7)
C10.0225 (12)0.0194 (11)0.0303 (13)0.0028 (10)0.0008 (10)0.0029 (9)
C20.0180 (11)0.0165 (11)0.0226 (11)0.0014 (8)0.0016 (9)0.0004 (8)
C30.0249 (12)0.0198 (11)0.0171 (11)0.0046 (9)0.0033 (9)0.0045 (9)
C40.0190 (10)0.0210 (12)0.0155 (10)0.0043 (9)0.0015 (8)0.0021 (8)
C50.0169 (10)0.0169 (10)0.0137 (10)0.0016 (8)0.0016 (8)0.0023 (8)
C60.0183 (10)0.0175 (11)0.0189 (10)0.0013 (9)0.0011 (8)0.0005 (8)
C70.0133 (9)0.0139 (10)0.0168 (10)0.0014 (8)0.0012 (8)0.0007 (8)
C80.0128 (10)0.0176 (10)0.0155 (10)0.0027 (8)0.0008 (8)0.0006 (8)
C90.0160 (10)0.0179 (11)0.0171 (10)0.0005 (9)0.0017 (8)0.0031 (8)
C100.0144 (10)0.0138 (10)0.0169 (10)0.0016 (8)0.0003 (8)0.0007 (8)
C110.0163 (10)0.0159 (11)0.0141 (10)0.0001 (8)0.0025 (8)0.0006 (8)
C120.0173 (10)0.0137 (10)0.0196 (11)0.0004 (8)0.0028 (9)0.0011 (8)
C130.0197 (10)0.0164 (10)0.0200 (11)0.0005 (9)0.0019 (9)0.0015 (8)
C140.0204 (11)0.0154 (10)0.0225 (11)0.0022 (8)0.0035 (9)0.0023 (8)
C150.0199 (11)0.0148 (10)0.0209 (11)0.0004 (8)0.0053 (9)0.0024 (8)
C160.0227 (11)0.0195 (11)0.0194 (11)0.0010 (9)0.0011 (9)0.0013 (8)
C170.0199 (11)0.0174 (11)0.0182 (11)0.0038 (9)0.0001 (9)0.0015 (8)
Geometric parameters (Å, º) top
O1—C21.379 (3)C7—C101.431 (3)
O1—C11.427 (3)C7—C81.448 (3)
O2—C101.238 (2)C8—C91.403 (3)
O3—C111.237 (2)C9—H90.9500
N1—C61.344 (3)C10—C111.534 (3)
N1—C51.389 (3)C12—C171.526 (3)
N1—H10.96 (3)C12—C131.528 (3)
N2—C111.331 (3)C12—H121.0000
N2—C121.465 (3)C13—C141.530 (3)
N2—H20.88 (3)C13—H13A0.9900
C1—H1A0.9800C13—H13B0.9900
C1—H1B0.9800C14—C151.534 (3)
C1—H1C0.9800C14—H14A0.9900
C2—C91.379 (3)C14—H14B0.9900
C2—C31.409 (3)C15—C161.524 (3)
C3—C41.375 (3)C15—H15A0.9900
C3—H30.9500C15—H15B0.9900
C4—C51.388 (3)C16—C171.532 (3)
C4—H40.9500C16—H16A0.9900
C5—C81.405 (3)C16—H16B0.9900
C6—C71.399 (3)C17—H17A0.9900
C6—H60.9500C17—H17B0.9900
C2—O1—C1116.63 (17)O3—C11—N2123.5 (2)
C6—N1—C5109.37 (18)O3—C11—C10121.94 (18)
C6—N1—H1122.6 (18)N2—C11—C10114.56 (18)
C5—N1—H1128.1 (18)N2—C12—C17112.11 (17)
C11—N2—C12120.74 (17)N2—C12—C13110.36 (18)
C11—N2—H2119.9 (18)C17—C12—C13110.58 (17)
C12—N2—H2119.2 (18)N2—C12—H12107.9
O1—C1—H1A109.5C17—C12—H12107.9
O1—C1—H1B109.5C13—C12—H12107.9
H1A—C1—H1B109.5C12—C13—C14110.68 (18)
O1—C1—H1C109.5C12—C13—H13A109.5
H1A—C1—H1C109.5C14—C13—H13A109.5
H1B—C1—H1C109.5C12—C13—H13B109.5
C9—C2—O1124.05 (18)C14—C13—H13B109.5
C9—C2—C3121.8 (2)H13A—C13—H13B108.1
O1—C2—C3114.11 (19)C13—C14—C15110.64 (18)
C4—C3—C2121.0 (2)C13—C14—H14A109.5
C4—C3—H3119.5C15—C14—H14A109.5
C2—C3—H3119.5C13—C14—H14B109.5
C3—C4—C5117.46 (19)C15—C14—H14B109.5
C3—C4—H4121.3H14A—C14—H14B108.1
C5—C4—H4121.3C16—C15—C14110.60 (18)
C4—C5—N1129.47 (18)C16—C15—H15A109.5
C4—C5—C8122.22 (19)C14—C15—H15A109.5
N1—C5—C8108.29 (18)C16—C15—H15B109.5
N1—C6—C7109.98 (19)C14—C15—H15B109.5
N1—C6—H6125.0H15A—C15—H15B108.1
C7—C6—H6125.0C15—C16—C17111.42 (19)
C6—C7—C10127.11 (19)C15—C16—H16A109.3
C6—C7—C8106.15 (17)C17—C16—H16A109.3
C10—C7—C8126.63 (17)C15—C16—H16B109.3
C9—C8—C5119.91 (19)C17—C16—H16B109.3
C9—C8—C7133.89 (18)H16A—C16—H16B108.0
C5—C8—C7106.20 (18)C12—C17—C16109.81 (17)
C2—C9—C8117.55 (18)C12—C17—H17A109.7
C2—C9—H9121.2C16—C17—H17A109.7
C8—C9—H9121.2C12—C17—H17B109.7
O2—C10—C7123.40 (19)C16—C17—H17B109.7
O2—C10—C11118.42 (18)H17A—C17—H17B108.2
C7—C10—C11118.15 (17)
C1—O1—C2—C91.3 (3)C5—C8—C9—C20.7 (3)
C1—O1—C2—C3177.67 (19)C7—C8—C9—C2179.7 (2)
C9—C2—C3—C40.6 (3)C6—C7—C10—O2174.9 (2)
O1—C2—C3—C4178.4 (2)C8—C7—C10—O20.7 (3)
C2—C3—C4—C50.1 (3)C6—C7—C10—C112.9 (3)
C3—C4—C5—N1179.4 (2)C8—C7—C10—C11178.55 (19)
C3—C4—C5—C81.2 (3)C12—N2—C11—O34.1 (3)
C6—N1—C5—C4178.7 (2)C12—N2—C11—C10175.09 (18)
C6—N1—C5—C80.3 (2)O2—C10—C11—O3148.5 (2)
C5—N1—C6—C70.2 (2)C7—C10—C11—O333.6 (3)
N1—C6—C7—C10176.2 (2)O2—C10—C11—N232.4 (3)
N1—C6—C7—C80.1 (2)C7—C10—C11—N2145.54 (19)
C4—C5—C8—C91.5 (3)C11—N2—C12—C1785.5 (2)
N1—C5—C8—C9179.95 (19)C11—N2—C12—C13150.80 (19)
C4—C5—C8—C7178.77 (19)N2—C12—C13—C14177.23 (17)
N1—C5—C8—C70.2 (2)C17—C12—C13—C1458.2 (2)
C6—C7—C8—C9179.8 (2)C12—C13—C14—C1556.8 (2)
C10—C7—C8—C93.9 (4)C13—C14—C15—C1655.7 (2)
C6—C7—C8—C50.1 (2)C14—C15—C16—C1756.4 (2)
C10—C7—C8—C5176.4 (2)N2—C12—C17—C16178.52 (17)
O1—C2—C9—C8178.57 (19)C13—C12—C17—C1657.9 (2)
C3—C2—C9—C80.4 (3)C15—C16—C17—C1257.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.96 (3)1.90 (3)2.840 (2)164 (3)
N2—H2···O3ii0.88 (3)2.09 (3)2.926 (3)160 (3)
Symmetry codes: (i) x+1, y, z1; (ii) x1, y, z.

Experimental details

Crystal data
Chemical formulaC17H20N2O3
Mr300.35
Crystal system, space groupMonoclinic, P21
Temperature (K)113
a, b, c (Å)5.083 (3), 27.336 (13), 5.220 (3)
β (°) 91.977 (12)
V3)724.9 (6)
Z2
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.20 × 0.18 × 0.10
Data collection
DiffractometerRigaku Saturn CCD area-detector
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2005)
Tmin, Tmax0.981, 0.991
No. of measured, independent and
observed [I > 2σ(I)] reflections
7342, 1764, 1569
Rint0.042
(sin θ/λ)max1)0.658
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.076, 1.02
No. of reflections1764
No. of parameters208
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.23, 0.18

Computer programs: CrystalClear (Rigaku, 2005), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.96 (3)1.90 (3)2.840 (2)164 (3)
N2—H2···O3ii0.88 (3)2.09 (3)2.926 (3)160 (3)
Symmetry codes: (i) x+1, y, z1; (ii) x1, y, z.
 

Acknowledgements

This work was supported by the National Natural Science Foundation of China (grant No. 30873363), the Program of the Science Foundation of Tianjin (grant No. 08JCYBJC070000) and the Major Program of the Science Foundation of Tianjin (grant No. 09ZCKFSH01700).

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