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

In title compound, C(16)H(17)FN(2)O(2), the cyclo-hexane ring adopts a chair conformation.. The crystal packing is stabilized by weak π-π stacking inter-actions [centroid-centroid distance = 3.503 (5) Å] and inter-molecular C-H⋯O, N-H⋯O and N-H⋯F hydrogen-bond inter-actions.

Related literature

For the biological activity of the title compound and its deriv­atives, see: Souli et al. (2008 ▶); Chai et al. (2006 ▶); Radwan et al. (2007 ▶); Karthikeyan et al. (2009 ▶). For the preparation, see: Bacher et al. (2001 ▶). For bond-length and angle data for similar structures, see: Liu et al. (2011 ▶); Sonar et al. (2006 ▶).

Experimental

Crystal data

C16H17FN2O2

M = 288.32

Monoclinic,

a = 11.5065 (15) Å

b = 9.7666 (12) Å

c = 12.3139 (16) Å

β = 96.639 (5)°

V = 1374.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 113 K

0.20 × 0.16 × 0.12 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.980, T max = 0.988

18432 measured reflections

3717 independent reflections

3007 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.098

S = 1.04

3717 reflections

198 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811024299/hg5056sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811024299/hg5056Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811024299/hg5056Isup3.cml

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

C16H17FN2O2	F(000) = 608
Mr = 288.32	Dx = 1.393 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5346 reflections
a = 11.5065 (15) Å	θ = 1.7–29.1°
b = 9.7666 (12) Å	µ = 0.10 mm−1
c = 12.3139 (16) Å	T = 113 K
β = 96.639 (5)°	Prism, colorless
V = 1374.5 (3) Å3	0.20 × 0.16 × 0.12 mm
Z = 4

Rigaku Saturn CCD area-detector diffractometer	3717 independent reflections
Radiation source: rotating anode	3007 reflections with I > 2σ(I)
multilayer	Rint = 0.035
Detector resolution: 14.63 pixels mm-1	θmax = 29.2°, θmin = 2.7°
ω and φ scans	h = −15→15
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −12→13
Tmin = 0.980, Tmax = 0.988	l = −16→16
18432 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0605P)2] where P = (Fo2 + 2Fc2)/3
3717 reflections	(Δ/σ)max = 0.001
198 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.28 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
F1	−0.25500 (5)	1.05586 (6)	0.22558 (5)	0.02199 (16)
O1	0.03563 (6)	0.68310 (7)	0.38752 (6)	0.01933 (17)
O2	0.10442 (6)	0.59789 (7)	0.66261 (6)	0.01922 (17)
N1	−0.11616 (7)	0.93484 (9)	0.65153 (7)	0.01534 (18)
N2	0.18874 (7)	0.53328 (8)	0.51269 (7)	0.01509 (18)
C1	−0.16319 (8)	0.97805 (10)	0.54839 (8)	0.0138 (2)
C2	−0.24187 (9)	1.08328 (10)	0.51989 (8)	0.0164 (2)
H2A	−0.2737	1.1364	0.5739	0.020*
C3	−0.27217 (8)	1.10769 (10)	0.40949 (8)	0.0167 (2)
H3	−0.3255	1.1788	0.3859	0.020*
C4	−0.22354 (9)	1.02687 (10)	0.33359 (8)	0.0156 (2)
C5	−0.14663 (8)	0.92118 (9)	0.35915 (8)	0.0140 (2)
H5	−0.1162	0.8682	0.3042	0.017*
C6	−0.11544 (8)	0.89560 (9)	0.47050 (8)	0.01231 (19)
C7	−0.03768 (8)	0.79970 (10)	0.53188 (7)	0.01268 (19)
C8	−0.04120 (8)	0.83109 (9)	0.64156 (8)	0.0141 (2)
H8	0.0030	0.7858	0.7009	0.017*
C9	0.03360 (8)	0.69899 (10)	0.48630 (7)	0.01308 (19)
C10	0.11288 (8)	0.60472 (9)	0.56399 (8)	0.0135 (2)
C11	0.26943 (8)	0.43341 (10)	0.56915 (8)	0.0150 (2)
H11	0.2231	0.3700	0.6112	0.018*
C12	0.36197 (9)	0.50230 (11)	0.64966 (9)	0.0204 (2)
H12A	0.3235	0.5562	0.7034	0.024*
H12B	0.4092	0.5657	0.6099	0.024*
C13	0.44143 (10)	0.39422 (12)	0.70913 (9)	0.0249 (3)
H13A	0.5025	0.4399	0.7597	0.030*
H13B	0.3948	0.3352	0.7530	0.030*
C14	0.49948 (9)	0.30599 (11)	0.62842 (9)	0.0229 (2)
H14A	0.5538	0.3632	0.5912	0.028*
H14B	0.5457	0.2328	0.6688	0.028*
C15	0.40945 (9)	0.24164 (10)	0.54345 (9)	0.0205 (2)
H15A	0.3630	0.1735	0.5795	0.025*
H15B	0.4503	0.1930	0.4884	0.025*
C16	0.32700 (8)	0.34877 (10)	0.48594 (8)	0.0168 (2)
H16A	0.3716	0.4100	0.4418	0.020*
H16B	0.2659	0.3024	0.4358	0.020*
H1	−0.1231 (12)	0.9799 (14)	0.7178 (12)	0.043 (4)*
H2	0.1848 (11)	0.5448 (12)	0.4395 (11)	0.027 (3)*

	U11	U22	U33	U12	U13	U23
F1	0.0241 (3)	0.0273 (3)	0.0137 (3)	0.0058 (3)	−0.0016 (2)	0.0056 (2)
O1	0.0251 (4)	0.0224 (4)	0.0100 (3)	0.0067 (3)	0.0000 (3)	−0.0008 (3)
O2	0.0269 (4)	0.0197 (4)	0.0110 (3)	0.0042 (3)	0.0019 (3)	0.0041 (3)
N1	0.0181 (4)	0.0177 (4)	0.0103 (4)	−0.0015 (3)	0.0018 (3)	−0.0032 (3)
N2	0.0171 (4)	0.0157 (4)	0.0121 (4)	0.0022 (3)	−0.0002 (3)	0.0017 (3)
C1	0.0145 (4)	0.0148 (5)	0.0118 (4)	−0.0030 (4)	0.0008 (3)	−0.0013 (3)
C2	0.0154 (5)	0.0157 (5)	0.0187 (5)	−0.0010 (4)	0.0035 (4)	−0.0036 (4)
C3	0.0141 (5)	0.0144 (5)	0.0214 (5)	0.0009 (4)	0.0011 (4)	0.0006 (4)
C4	0.0160 (5)	0.0179 (5)	0.0123 (5)	−0.0020 (4)	−0.0013 (3)	0.0023 (4)
C5	0.0153 (5)	0.0148 (5)	0.0119 (5)	−0.0015 (4)	0.0013 (3)	−0.0011 (3)
C6	0.0129 (4)	0.0124 (4)	0.0116 (4)	−0.0022 (4)	0.0014 (3)	−0.0004 (3)
C7	0.0143 (4)	0.0132 (4)	0.0102 (4)	−0.0028 (4)	0.0002 (3)	0.0004 (3)
C8	0.0154 (4)	0.0150 (5)	0.0116 (5)	−0.0027 (4)	0.0006 (3)	−0.0001 (3)
C9	0.0149 (4)	0.0136 (4)	0.0102 (4)	−0.0024 (4)	−0.0006 (3)	0.0005 (3)
C10	0.0162 (5)	0.0116 (4)	0.0122 (4)	−0.0025 (4)	0.0000 (3)	0.0007 (3)
C11	0.0148 (5)	0.0143 (5)	0.0154 (5)	0.0006 (4)	−0.0010 (4)	0.0022 (4)
C12	0.0193 (5)	0.0202 (5)	0.0200 (5)	0.0004 (4)	−0.0041 (4)	−0.0017 (4)
C13	0.0211 (5)	0.0283 (6)	0.0230 (6)	0.0024 (5)	−0.0071 (4)	0.0016 (4)
C14	0.0163 (5)	0.0217 (5)	0.0295 (6)	0.0023 (4)	−0.0027 (4)	0.0053 (4)
C15	0.0173 (5)	0.0164 (5)	0.0277 (6)	0.0010 (4)	0.0020 (4)	0.0012 (4)
C16	0.0154 (5)	0.0162 (5)	0.0185 (5)	−0.0009 (4)	0.0007 (4)	0.0003 (4)

F1—C4	1.3671 (11)	C7—C9	1.4358 (14)
O1—C9	1.2291 (11)	C8—H8	0.9500
O2—C10	1.2313 (12)	C9—C10	1.5470 (13)
N1—C8	1.3454 (13)	C11—C12	1.5249 (14)
N1—C1	1.3874 (12)	C11—C16	1.5261 (14)
N1—H1	0.939 (14)	C11—H11	1.0000
N2—C10	1.3324 (13)	C12—C13	1.5270 (14)
N2—C11	1.4655 (12)	C12—H12A	0.9900
N2—H2	0.905 (13)	C12—H12B	0.9900
C1—C2	1.3877 (14)	C13—C14	1.5265 (16)
C1—C6	1.4113 (13)	C13—H13A	0.9900
C2—C3	1.3846 (14)	C13—H13B	0.9900
C2—H2A	0.9500	C14—C15	1.5206 (14)
C3—C4	1.3895 (14)	C14—H14A	0.9900
C3—H3	0.9500	C14—H14B	0.9900
C4—C5	1.3723 (14)	C15—C16	1.5300 (13)
C5—C6	1.3992 (13)	C15—H15A	0.9900
C5—H5	0.9500	C15—H15B	0.9900
C6—C7	1.4466 (13)	C16—H16A	0.9900
C7—C8	1.3901 (13)	C16—H16B	0.9900
C8—N1—C1	109.38 (8)	N2—C11—C12	111.79 (8)
C8—N1—H1	123.5 (9)	N2—C11—C16	110.02 (8)
C1—N1—H1	126.2 (9)	C12—C11—C16	110.54 (8)
C10—N2—C11	122.51 (8)	N2—C11—H11	108.1
C10—N2—H2	116.5 (8)	C12—C11—H11	108.1
C11—N2—H2	120.8 (8)	C16—C11—H11	108.1
N1—C1—C2	129.11 (9)	C11—C12—C13	109.95 (8)
N1—C1—C6	107.90 (9)	C11—C12—H12A	109.7
C2—C1—C6	122.99 (9)	C13—C12—H12A	109.7
C3—C2—C1	117.30 (9)	C11—C12—H12B	109.7
C3—C2—H2A	121.3	C13—C12—H12B	109.7
C1—C2—H2A	121.3	H12A—C12—H12B	108.2
C2—C3—C4	119.17 (9)	C14—C13—C12	111.15 (9)
C2—C3—H3	120.4	C14—C13—H13A	109.4
C4—C3—H3	120.4	C12—C13—H13A	109.4
F1—C4—C5	118.04 (9)	C14—C13—H13B	109.4
F1—C4—C3	117.05 (9)	C12—C13—H13B	109.4
C5—C4—C3	124.91 (9)	H13A—C13—H13B	108.0
C4—C5—C6	116.40 (9)	C15—C14—C13	111.51 (8)
C4—C5—H5	121.8	C15—C14—H14A	109.3
C6—C5—H5	121.8	C13—C14—H14A	109.3
C5—C6—C1	119.23 (9)	C15—C14—H14B	109.3
C5—C6—C7	134.48 (9)	C13—C14—H14B	109.3
C1—C6—C7	106.27 (8)	H14A—C14—H14B	108.0
C8—C7—C9	127.81 (9)	C14—C15—C16	111.87 (8)
C8—C7—C6	106.20 (8)	C14—C15—H15A	109.2
C9—C7—C6	125.88 (8)	C16—C15—H15A	109.2
N1—C8—C7	110.23 (8)	C14—C15—H15B	109.2
N1—C8—H8	124.9	C16—C15—H15B	109.2
C7—C8—H8	124.9	H15A—C15—H15B	107.9
O1—C9—C7	123.40 (9)	C11—C16—C15	110.71 (8)
O1—C9—C10	117.35 (8)	C11—C16—H16A	109.5
C7—C9—C10	119.25 (8)	C15—C16—H16A	109.5
O2—C10—N2	124.75 (9)	C11—C16—H16B	109.5
O2—C10—C9	122.28 (8)	C15—C16—H16B	109.5
N2—C10—C9	112.97 (8)	H16A—C16—H16B	108.1
C8—N1—C1—C2	−178.59 (10)	C6—C7—C8—N1	1.51 (10)
C8—N1—C1—C6	0.56 (11)	C8—C7—C9—O1	−175.91 (9)
N1—C1—C2—C3	178.08 (9)	C6—C7—C9—O1	−0.28 (16)
C6—C1—C2—C3	−0.96 (14)	C8—C7—C9—C10	3.92 (15)
C1—C2—C3—C4	0.18 (14)	C6—C7—C9—C10	179.56 (8)
C2—C3—C4—F1	−179.24 (8)	C11—N2—C10—O2	2.07 (15)
C2—C3—C4—C5	0.59 (15)	C11—N2—C10—C9	−177.56 (8)
F1—C4—C5—C6	179.28 (8)	O1—C9—C10—O2	−168.77 (9)
C3—C4—C5—C6	−0.55 (15)	C7—C9—C10—O2	11.39 (14)
C4—C5—C6—C1	−0.23 (13)	O1—C9—C10—N2	10.87 (12)
C4—C5—C6—C7	−178.32 (10)	C7—C9—C10—N2	−168.98 (9)
N1—C1—C6—C5	−178.22 (8)	C10—N2—C11—C12	−68.08 (12)
C2—C1—C6—C5	1.00 (14)	C10—N2—C11—C16	168.70 (8)
N1—C1—C6—C7	0.37 (10)	N2—C11—C12—C13	178.16 (8)
C2—C1—C6—C7	179.58 (9)	C16—C11—C12—C13	−58.92 (11)
C5—C6—C7—C8	177.15 (10)	C11—C12—C13—C14	57.56 (12)
C1—C6—C7—C8	−1.12 (10)	C12—C13—C14—C15	−54.88 (12)
C5—C6—C7—C9	0.74 (17)	C13—C14—C15—C16	53.30 (12)
C1—C6—C7—C9	−177.53 (9)	N2—C11—C16—C15	−178.68 (8)
C1—N1—C8—C7	−1.32 (11)	C12—C11—C16—C15	57.37 (11)
C9—C7—C8—N1	177.83 (9)	C14—C15—C16—C11	−54.54 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···F1i	0.905 (13)	2.275 (13)	3.1234 (11)	156.1 (11)
N1—H1···O2ii	0.939 (14)	1.863 (14)	2.7786 (11)	164.5 (13)
C8—H8···O1iii	0.95	2.31	3.0586 (12)	136.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯F1i	0.905 (13)	2.275 (13)	3.1234 (11)	156.1 (11)
N1—H1⋯O2ii	0.939 (14)	1.863 (14)	2.7786 (11)	164.5 (13)
C8—H8⋯O1iii	0.95	2.31	3.0586 (12)	136

Symmetry codes: (i) ; (ii) ; (iii) .