N-Cyclo-hexyl-2-(5-meth-oxy-1H-indol-3-yl)-2-oxoacetamide.

In the title compound, C(17)H(20)N(2)O(3), the cyclo-hexane ring adopts a chair conformation. In the crystal, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into layers parallel to the ac plane.

Related literature

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

Crystal data

C17H20N2O3

M = 300.35

Monoclinic,

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 ▶) T min = 0.981, T max = 0.991

7342 measured reflections

1764 independent reflections

1569 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 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

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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810054656/cv5025sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810054656/cv5025Isup2.hkl

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

C17H20N2O3	F(000) = 320
Mr = 300.35	Dx = 1.376 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2636 reflections
a = 5.083 (3) Å	θ = 1.5–27.9°
b = 27.336 (13) Å	µ = 0.10 mm−1
c = 5.220 (3) Å	T = 113 K
β = 91.977 (12)°	Prism, colourless
V = 724.9 (6) Å3	0.20 × 0.18 × 0.10 mm
Z = 2

Rigaku Saturn CCD area-detector diffractometer	1764 independent reflections
Radiation source: rotating anode	1569 reflections with I > 2σ(I)
multilayer	Rint = 0.042
Detector resolution: 14.63 pixels mm-1	θmax = 27.9°, θmin = 1.5°
ω and φ scans	h = −6→6
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −36→31
Tmin = 0.981, Tmax = 0.991	l = −6→6
7342 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076	H 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 parameters	Δρmax = 0.23 e Å−3
1 restraint	Δρmin = −0.18 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. 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.

	x	y	z	Uiso*/Ueq
O1	−0.1844 (3)	0.03318 (6)	0.3071 (3)	0.0242 (4)
O2	−0.1506 (3)	0.20016 (5)	0.8241 (3)	0.0181 (3)
O3	0.3519 (3)	0.28545 (6)	0.8311 (3)	0.0209 (4)
N1	0.4663 (4)	0.19176 (7)	0.2050 (3)	0.0175 (4)
N2	−0.0791 (4)	0.29907 (6)	0.8997 (3)	0.0167 (4)
C1	−0.3621 (4)	0.03287 (9)	0.5127 (5)	0.0241 (5)
H1A	−0.2627	0.0360	0.6761	0.036*
H1B	−0.4607	0.0021	0.5106	0.036*
H1C	−0.4851	0.0603	0.4927	0.036*
C2	−0.0281 (4)	0.07411 (8)	0.2854 (4)	0.0191 (5)
C3	0.1505 (4)	0.07156 (8)	0.0851 (4)	0.0207 (5)
H3	0.1508	0.0435	−0.0223	0.025*
C4	0.3242 (4)	0.10905 (8)	0.0430 (4)	0.0185 (4)
H4	0.4446	0.1075	−0.0920	0.022*
C5	0.3169 (4)	0.14924 (7)	0.2052 (4)	0.0158 (4)
C6	0.3895 (4)	0.22142 (8)	0.3936 (4)	0.0182 (4)
H6	0.4632	0.2526	0.4319	0.022*
C7	0.1850 (4)	0.19958 (8)	0.5251 (4)	0.0147 (4)
C8	0.1372 (4)	0.15268 (8)	0.4031 (4)	0.0153 (4)
C9	−0.0386 (4)	0.11418 (8)	0.4453 (4)	0.0170 (4)
H9	−0.1603	0.1156	0.5792	0.020*
C10	0.0403 (4)	0.22048 (7)	0.7283 (4)	0.0150 (4)
C11	0.1203 (4)	0.27147 (7)	0.8258 (4)	0.0154 (4)
C12	−0.0360 (4)	0.35000 (7)	0.9780 (4)	0.0168 (4)
H12	0.1085	0.3636	0.8739	0.020*
C13	−0.2834 (4)	0.38039 (8)	0.9209 (4)	0.0187 (4)
H13A	−0.4302	0.3675	1.0208	0.022*
H13B	−0.3340	0.3777	0.7366	0.022*
C14	−0.2356 (5)	0.43413 (8)	0.9899 (4)	0.0194 (5)
H14A	−0.4000	0.4529	0.9587	0.023*
H14B	−0.0995	0.4478	0.8793	0.023*
C15	−0.1453 (4)	0.43918 (8)	1.2721 (4)	0.0184 (4)
H15A	−0.1048	0.4739	1.3106	0.022*
H15B	−0.2888	0.4287	1.3832	0.022*
C16	0.0984 (4)	0.40803 (8)	1.3293 (4)	0.0205 (5)
H16A	0.1486	0.4106	1.5137	0.025*
H16B	0.2466	0.4206	1.2301	0.025*
C17	0.0493 (4)	0.35425 (8)	1.2602 (4)	0.0185 (5)
H17A	0.2123	0.3351	1.2934	0.022*
H17B	−0.0897	0.3408	1.3682	0.022*
H1	0.603 (6)	0.2006 (11)	0.090 (6)	0.042 (8)*
H2	−0.240 (5)	0.2875 (10)	0.891 (5)	0.027 (7)*

	U11	U22	U33	U12	U13	U23
O1	0.0251 (8)	0.0167 (8)	0.0310 (9)	−0.0030 (7)	0.0032 (7)	−0.0044 (7)
O2	0.0158 (7)	0.0174 (8)	0.0214 (8)	−0.0014 (6)	0.0052 (6)	−0.0016 (6)
O3	0.0157 (7)	0.0193 (8)	0.0277 (9)	−0.0012 (6)	0.0022 (6)	−0.0038 (6)
N1	0.0182 (9)	0.0182 (9)	0.0167 (9)	0.0019 (7)	0.0070 (7)	−0.0002 (7)
N2	0.0132 (9)	0.0159 (9)	0.0211 (10)	−0.0008 (7)	0.0020 (7)	−0.0023 (7)
C1	0.0225 (12)	0.0194 (11)	0.0303 (13)	−0.0028 (10)	0.0008 (10)	0.0029 (9)
C2	0.0180 (11)	0.0165 (11)	0.0226 (11)	0.0014 (8)	−0.0016 (9)	−0.0004 (8)
C3	0.0249 (12)	0.0198 (11)	0.0171 (11)	0.0046 (9)	−0.0033 (9)	−0.0045 (9)
C4	0.0190 (10)	0.0210 (12)	0.0155 (10)	0.0043 (9)	0.0015 (8)	−0.0021 (8)
C5	0.0169 (10)	0.0169 (10)	0.0137 (10)	0.0016 (8)	0.0016 (8)	0.0023 (8)
C6	0.0183 (10)	0.0175 (11)	0.0189 (10)	0.0013 (9)	0.0011 (8)	0.0005 (8)
C7	0.0133 (9)	0.0139 (10)	0.0168 (10)	0.0014 (8)	0.0012 (8)	0.0007 (8)
C8	0.0128 (10)	0.0176 (10)	0.0155 (10)	0.0027 (8)	0.0008 (8)	0.0006 (8)
C9	0.0160 (10)	0.0179 (11)	0.0171 (10)	0.0005 (9)	0.0017 (8)	0.0031 (8)
C10	0.0144 (10)	0.0138 (10)	0.0169 (10)	0.0016 (8)	0.0003 (8)	0.0007 (8)
C11	0.0163 (10)	0.0159 (11)	0.0141 (10)	−0.0001 (8)	0.0025 (8)	0.0006 (8)
C12	0.0173 (10)	0.0137 (10)	0.0196 (11)	0.0004 (8)	0.0028 (9)	−0.0011 (8)
C13	0.0197 (10)	0.0164 (10)	0.0200 (11)	0.0005 (9)	0.0019 (9)	−0.0015 (8)
C14	0.0204 (11)	0.0154 (10)	0.0225 (11)	0.0022 (8)	0.0035 (9)	0.0023 (8)
C15	0.0199 (11)	0.0148 (10)	0.0209 (11)	0.0004 (8)	0.0053 (9)	−0.0024 (8)
C16	0.0227 (11)	0.0195 (11)	0.0194 (11)	0.0010 (9)	0.0011 (9)	−0.0013 (8)
C17	0.0199 (11)	0.0174 (11)	0.0182 (11)	0.0038 (9)	0.0001 (9)	−0.0015 (8)

O1—C2	1.379 (3)	C7—C10	1.431 (3)
O1—C1	1.427 (3)	C7—C8	1.448 (3)
O2—C10	1.238 (2)	C8—C9	1.403 (3)
O3—C11	1.237 (2)	C9—H9	0.9500
N1—C6	1.344 (3)	C10—C11	1.534 (3)
N1—C5	1.389 (3)	C12—C17	1.526 (3)
N1—H1	0.96 (3)	C12—C13	1.528 (3)
N2—C11	1.331 (3)	C12—H12	1.0000
N2—C12	1.465 (3)	C13—C14	1.530 (3)
N2—H2	0.88 (3)	C13—H13A	0.9900
C1—H1A	0.9800	C13—H13B	0.9900
C1—H1B	0.9800	C14—C15	1.534 (3)
C1—H1C	0.9800	C14—H14A	0.9900
C2—C9	1.379 (3)	C14—H14B	0.9900
C2—C3	1.409 (3)	C15—C16	1.524 (3)
C3—C4	1.375 (3)	C15—H15A	0.9900
C3—H3	0.9500	C15—H15B	0.9900
C4—C5	1.388 (3)	C16—C17	1.532 (3)
C4—H4	0.9500	C16—H16A	0.9900
C5—C8	1.405 (3)	C16—H16B	0.9900
C6—C7	1.399 (3)	C17—H17A	0.9900
C6—H6	0.9500	C17—H17B	0.9900
C2—O1—C1	116.63 (17)	O3—C11—N2	123.5 (2)
C6—N1—C5	109.37 (18)	O3—C11—C10	121.94 (18)
C6—N1—H1	122.6 (18)	N2—C11—C10	114.56 (18)
C5—N1—H1	128.1 (18)	N2—C12—C17	112.11 (17)
C11—N2—C12	120.74 (17)	N2—C12—C13	110.36 (18)
C11—N2—H2	119.9 (18)	C17—C12—C13	110.58 (17)
C12—N2—H2	119.2 (18)	N2—C12—H12	107.9
O1—C1—H1A	109.5	C17—C12—H12	107.9
O1—C1—H1B	109.5	C13—C12—H12	107.9
H1A—C1—H1B	109.5	C12—C13—C14	110.68 (18)
O1—C1—H1C	109.5	C12—C13—H13A	109.5
H1A—C1—H1C	109.5	C14—C13—H13A	109.5
H1B—C1—H1C	109.5	C12—C13—H13B	109.5
C9—C2—O1	124.05 (18)	C14—C13—H13B	109.5
C9—C2—C3	121.8 (2)	H13A—C13—H13B	108.1
O1—C2—C3	114.11 (19)	C13—C14—C15	110.64 (18)
C4—C3—C2	121.0 (2)	C13—C14—H14A	109.5
C4—C3—H3	119.5	C15—C14—H14A	109.5
C2—C3—H3	119.5	C13—C14—H14B	109.5
C3—C4—C5	117.46 (19)	C15—C14—H14B	109.5
C3—C4—H4	121.3	H14A—C14—H14B	108.1
C5—C4—H4	121.3	C16—C15—C14	110.60 (18)
C4—C5—N1	129.47 (18)	C16—C15—H15A	109.5
C4—C5—C8	122.22 (19)	C14—C15—H15A	109.5
N1—C5—C8	108.29 (18)	C16—C15—H15B	109.5
N1—C6—C7	109.98 (19)	C14—C15—H15B	109.5
N1—C6—H6	125.0	H15A—C15—H15B	108.1
C7—C6—H6	125.0	C15—C16—C17	111.42 (19)
C6—C7—C10	127.11 (19)	C15—C16—H16A	109.3
C6—C7—C8	106.15 (17)	C17—C16—H16A	109.3
C10—C7—C8	126.63 (17)	C15—C16—H16B	109.3
C9—C8—C5	119.91 (19)	C17—C16—H16B	109.3
C9—C8—C7	133.89 (18)	H16A—C16—H16B	108.0
C5—C8—C7	106.20 (18)	C12—C17—C16	109.81 (17)
C2—C9—C8	117.55 (18)	C12—C17—H17A	109.7
C2—C9—H9	121.2	C16—C17—H17A	109.7
C8—C9—H9	121.2	C12—C17—H17B	109.7
O2—C10—C7	123.40 (19)	C16—C17—H17B	109.7
O2—C10—C11	118.42 (18)	H17A—C17—H17B	108.2
C7—C10—C11	118.15 (17)
C1—O1—C2—C9	−1.3 (3)	C5—C8—C9—C2	−0.7 (3)
C1—O1—C2—C3	177.67 (19)	C7—C8—C9—C2	179.7 (2)
C9—C2—C3—C4	0.6 (3)	C6—C7—C10—O2	174.9 (2)
O1—C2—C3—C4	−178.4 (2)	C8—C7—C10—O2	−0.7 (3)
C2—C3—C4—C5	0.1 (3)	C6—C7—C10—C11	−2.9 (3)
C3—C4—C5—N1	−179.4 (2)	C8—C7—C10—C11	−178.55 (19)
C3—C4—C5—C8	−1.2 (3)	C12—N2—C11—O3	4.1 (3)
C6—N1—C5—C4	178.7 (2)	C12—N2—C11—C10	−175.09 (18)
C6—N1—C5—C8	0.3 (2)	O2—C10—C11—O3	148.5 (2)
C5—N1—C6—C7	−0.2 (2)	C7—C10—C11—O3	−33.6 (3)
N1—C6—C7—C10	−176.2 (2)	O2—C10—C11—N2	−32.4 (3)
N1—C6—C7—C8	0.1 (2)	C7—C10—C11—N2	145.54 (19)
C4—C5—C8—C9	1.5 (3)	C11—N2—C12—C17	−85.5 (2)
N1—C5—C8—C9	−179.95 (19)	C11—N2—C12—C13	150.80 (19)
C4—C5—C8—C7	−178.77 (19)	N2—C12—C13—C14	−177.23 (17)
N1—C5—C8—C7	−0.2 (2)	C17—C12—C13—C14	58.2 (2)
C6—C7—C8—C9	179.8 (2)	C12—C13—C14—C15	−56.8 (2)
C10—C7—C8—C9	−3.9 (4)	C13—C14—C15—C16	55.7 (2)
C6—C7—C8—C5	0.1 (2)	C14—C15—C16—C17	−56.4 (2)
C10—C7—C8—C5	176.4 (2)	N2—C12—C17—C16	178.52 (17)
O1—C2—C9—C8	178.57 (19)	C13—C12—C17—C16	−57.9 (2)
C3—C2—C9—C8	−0.4 (3)	C15—C16—C17—C12	57.4 (2)

D—H···A	D—H	H···A	D···A	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)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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) ; (ii) .