Methyl 2-(5-fluoro-1H-indol-3-yl)-2-oxoacetate.

The indolyl portion of the title mol-ecule, C(11)H(8)FNO(3), is flat, the five- and six-membered rings making a dihedral angle of 0.815 (6)°. Inter-molecular N-H⋯O hydrogen bonds link adjacent mol-ecules into a linear chain. Slipped π-π stacking inter-actions between two neighboring indole groups further consolidate the mol-ecules into a three-dimensional supra-molecular architecture [centroid-centroid distances = 3.555 (10) and 3.569 (10) Å].

Related literature

For the biological activity of the title compound and its derivatives, see: Kozikowski et al. (2006 ▶); Albert et al. (2002 ▶); Jaquith et al. (2005 ▶). For the preparation, see: Alawar et al. (2004 ▶).

Experimental

Crystal data

C11H8FNO3

M = 221.18

Monoclinic,

a = 7.0584 (14) Å

b = 20.586 (4) Å

c = 7.3286 (15) Å

β = 112.01 (3)°

V = 987.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 113 K

0.30 × 0.24 × 0.20 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2004 ▶) T min = 0.964, T max = 0.976

9472 measured reflections

2328 independent reflections

2097 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.097

S = 1.06

2328 reflections

150 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2004 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXL97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809053033/ng2701sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809053033/ng2701Isup2.hkl

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

C11H8FNO3	F(000) = 456
Mr = 221.18	Dx = 1.488 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2958 reflections
a = 7.0584 (14) Å	θ = 3.1–27.9°
b = 20.586 (4) Å	µ = 0.12 mm−1
c = 7.3286 (15) Å	T = 113 K
β = 112.01 (3)°	Block, colorless
V = 987.3 (3) Å3	0.30 × 0.24 × 0.20 mm
Z = 4

Rigaku Saturn CCD area-detector diffractometer	2328 independent reflections
Radiation source: rotating anode	2097 reflections with I > 2σ(I)
multilayer	Rint = 0.024
Detector resolution: 7.31 pixels mm-1	θmax = 27.9°, θmin = 3.1°
ω and φ scans	h = −9→8
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2004)	k = −27→26
Tmin = 0.964, Tmax = 0.976	l = −9→9
9472 measured reflections

Refinement on F2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.037	w = 1/[σ2(Fo2) + (0.0503P)2 + 0.338P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.097	(Δ/σ)max = 0.001
S = 1.06	Δρmax = 0.38 e Å−3
2328 reflections	Δρmin = −0.20 e Å−3
150 parameters

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	0.12543 (14)	0.29293 (3)	0.65340 (12)	0.0361 (2)
O1	0.26544 (13)	0.51327 (4)	0.99608 (11)	0.02011 (19)
O2	0.38836 (16)	0.66111 (4)	0.83866 (13)	0.0297 (2)
N1	0.26610 (14)	0.52509 (5)	0.37504 (13)	0.0173 (2)
O3	0.28315 (14)	0.63607 (4)	1.08373 (12)	0.0244 (2)
C1	0.23060 (16)	0.46201 (5)	0.42115 (15)	0.0162 (2)
C2	0.19687 (18)	0.40616 (6)	0.30676 (16)	0.0215 (2)
H2	0.1971	0.4072	0.1772	0.026*
C3	0.16302 (19)	0.34900 (6)	0.38896 (18)	0.0247 (3)
H3	0.1396	0.3095	0.3167	0.030*
C4	0.16368 (19)	0.35010 (5)	0.57927 (18)	0.0232 (3)
C5	0.20002 (17)	0.40431 (5)	0.69689 (16)	0.0187 (2)
H5	0.2012	0.4025	0.8269	0.022*
C6	0.23508 (16)	0.46224 (5)	0.61507 (15)	0.0149 (2)
C7	0.27633 (15)	0.52844 (5)	0.68412 (15)	0.0146 (2)
C8	0.29297 (16)	0.56415 (5)	0.52914 (15)	0.0161 (2)
H8	0.3194	0.6095	0.5323	0.019*
C9	0.28704 (16)	0.55005 (5)	0.87314 (15)	0.0151 (2)
C10	0.32621 (17)	0.62255 (5)	0.92560 (15)	0.0183 (2)
C11	0.3146 (2)	0.70317 (6)	1.14936 (19)	0.0327 (3)
H11A	0.4534	0.7166	1.1666	0.049*
H11B	0.2962	0.7072	1.2749	0.049*
H11C	0.2154	0.7310	1.0508	0.049*
H1	0.271 (2)	0.5363 (8)	0.253 (2)	0.036 (4)*

	U11	U22	U33	U12	U13	U23
F1	0.0544 (5)	0.0165 (3)	0.0358 (4)	−0.0065 (3)	0.0150 (4)	0.0025 (3)
O1	0.0294 (4)	0.0200 (4)	0.0134 (4)	−0.0006 (3)	0.0109 (3)	0.0013 (3)
O2	0.0479 (6)	0.0199 (4)	0.0264 (5)	−0.0071 (4)	0.0198 (4)	−0.0019 (3)
N1	0.0195 (5)	0.0220 (5)	0.0121 (4)	0.0002 (3)	0.0079 (4)	0.0007 (3)
O3	0.0397 (5)	0.0183 (4)	0.0178 (4)	0.0013 (3)	0.0141 (4)	−0.0039 (3)
C1	0.0150 (5)	0.0207 (5)	0.0134 (5)	0.0013 (4)	0.0058 (4)	−0.0006 (4)
C2	0.0218 (6)	0.0264 (6)	0.0171 (5)	0.0010 (4)	0.0082 (4)	−0.0057 (4)
C3	0.0263 (6)	0.0214 (5)	0.0247 (6)	0.0004 (4)	0.0077 (5)	−0.0078 (4)
C4	0.0266 (6)	0.0162 (5)	0.0254 (6)	−0.0003 (4)	0.0080 (5)	0.0022 (4)
C5	0.0209 (5)	0.0189 (5)	0.0155 (5)	0.0007 (4)	0.0061 (4)	0.0017 (4)
C6	0.0136 (5)	0.0184 (5)	0.0126 (5)	0.0012 (4)	0.0047 (4)	−0.0003 (4)
C7	0.0149 (5)	0.0174 (5)	0.0120 (5)	0.0011 (4)	0.0056 (4)	0.0009 (4)
C8	0.0167 (5)	0.0191 (5)	0.0130 (5)	0.0002 (4)	0.0061 (4)	0.0010 (4)
C9	0.0161 (5)	0.0170 (5)	0.0125 (5)	0.0010 (4)	0.0056 (4)	0.0000 (4)
C10	0.0219 (5)	0.0190 (5)	0.0130 (5)	0.0017 (4)	0.0054 (4)	−0.0007 (4)
C11	0.0547 (9)	0.0191 (6)	0.0251 (6)	0.0038 (5)	0.0158 (6)	−0.0059 (5)

F1—C4	1.3650 (13)	C3—H3	0.9500
O1—C9	1.2295 (13)	C4—C5	1.3742 (16)
O2—C10	1.1992 (14)	C5—C6	1.3978 (14)
N1—C8	1.3406 (13)	C5—H5	0.9500
N1—C1	1.3881 (14)	C6—C7	1.4450 (14)
N1—H1	0.932 (17)	C7—C8	1.3943 (14)
O3—C10	1.3330 (13)	C7—C9	1.4297 (14)
O3—C11	1.4520 (14)	C8—H8	0.9500
C1—C2	1.3898 (15)	C9—C10	1.5400 (15)
C1—C6	1.4097 (14)	C11—H11A	0.9800
C2—C3	1.3829 (17)	C11—H11B	0.9800
C2—H2	0.9500	C11—H11C	0.9800
C3—C4	1.3932 (17)
C8—N1—C1	109.72 (9)	C5—C6—C7	134.36 (9)
C8—N1—H1	127.7 (10)	C1—C6—C7	106.36 (9)
C1—N1—H1	122.6 (10)	C8—C7—C9	129.44 (10)
C10—O3—C11	115.49 (9)	C8—C7—C6	106.22 (9)
N1—C1—C2	129.26 (10)	C9—C7—C6	124.29 (9)
N1—C1—C6	107.72 (9)	N1—C8—C7	109.97 (9)
C2—C1—C6	123.02 (10)	N1—C8—H8	125.0
C3—C2—C1	117.37 (10)	C7—C8—H8	125.0
C3—C2—H2	121.3	O1—C9—C7	122.84 (10)
C1—C2—H2	121.3	O1—C9—C10	118.29 (9)
C2—C3—C4	119.07 (10)	C7—C9—C10	118.87 (9)
C2—C3—H3	120.5	O2—C10—O3	124.87 (10)
C4—C3—H3	120.5	O2—C10—C9	125.17 (10)
F1—C4—C5	117.96 (11)	O3—C10—C9	109.96 (9)
F1—C4—C3	117.22 (10)	O3—C11—H11A	109.5
C5—C4—C3	124.82 (11)	O3—C11—H11B	109.5
C4—C5—C6	116.43 (10)	H11A—C11—H11B	109.5
C4—C5—H5	121.8	O3—C11—H11C	109.5
C6—C5—H5	121.8	H11A—C11—H11C	109.5
C5—C6—C1	119.27 (9)	H11B—C11—H11C	109.5
C8—N1—C1—C2	−179.36 (11)	C1—C6—C7—C8	0.36 (11)
C8—N1—C1—C6	0.23 (12)	C5—C6—C7—C9	−1.23 (19)
N1—C1—C2—C3	−179.31 (11)	C1—C6—C7—C9	177.96 (10)
C6—C1—C2—C3	1.15 (17)	C1—N1—C8—C7	0.00 (12)
C1—C2—C3—C4	0.19 (17)	C9—C7—C8—N1	−177.67 (10)
C2—C3—C4—F1	178.67 (11)	C6—C7—C8—N1	−0.23 (12)
C2—C3—C4—C5	−1.38 (19)	C8—C7—C9—O1	178.43 (11)
F1—C4—C5—C6	−178.92 (10)	C6—C7—C9—O1	1.41 (17)
C3—C4—C5—C6	1.13 (18)	C8—C7—C9—C10	−1.25 (17)
C4—C5—C6—C1	0.25 (15)	C6—C7—C9—C10	−178.28 (10)
C4—C5—C6—C7	179.36 (12)	C11—O3—C10—O2	0.50 (17)
N1—C1—C6—C5	178.98 (10)	C11—O3—C10—C9	179.76 (10)
C2—C1—C6—C5	−1.40 (16)	O1—C9—C10—O2	164.82 (12)
N1—C1—C6—C7	−0.36 (11)	C7—C9—C10—O2	−15.49 (17)
C2—C1—C6—C7	179.26 (10)	O1—C9—C10—O3	−14.44 (14)
C5—C6—C7—C8	−178.83 (12)	C7—C9—C10—O3	165.25 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3i	0.932 (17)	2.420 (16)	3.1598 (13)	136.3 (13)
N1—H1···O1i	0.932 (17)	1.932 (17)	2.7861 (13)	151.3 (14)
C3—H3···F1ii	0.95	2.41	3.3532 (15)	173
C5—H5···O1	0.95	2.55	3.0484 (14)	113
C8—H8···O2	0.95	2.36	2.9049 (14)	116

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3i	0.932 (17)	2.420 (16)	3.1598 (13)	136.3 (13)
N1—H1⋯O1i	0.932 (17)	1.932 (17)	2.7861 (13)	151.3 (14)

Symmetry code: (i) .