Ethyl 3,3,3-trifluoro-2-hy-droxy-2-(5-meth-oxy-1H-indol-3-yl)propionate.

In the title compound, C(14)H(14)F(3)NO(4), the 3,3,3-trifluoro-pyruvate fragment has a syn configuration and is noncoplanar with the indole plane [dihedral angle = 84.87 (5)°]. In the crystal, mol-ecules form inversion-related dimers via pairs of inter-molecular O-H⋯O hydrogen bonds. These dimers are connected by inter-molecular N-H⋯O=C(CF(3)) hydrogen bonds to form a two-dimensional network structure.

Related literature

For background on the synthesis and activity of trifluoro­pyruvates of indole, see: Nakamura et al. (2008 ▶); Abid et al. (2008 ▶). For the crystal structures of related compounds, see: Choudhury et al. (2004 ▶); Abid et al. (2008 ▶).

Experimental

Crystal data

C14H14F3NO4

M = 317.26

Monoclinic,

a = 9.6277 (4) Å

b = 15.9760 (6) Å

c = 9.9738 (4) Å

β = 109.314 (5)°

V = 1447.75 (10) Å3

Z = 4

Cu Kα radiation

μ = 1.15 mm−1

T = 293 K

0.55 × 0.45 × 0.40 mm

Data collection

Oxford Diffraction Xcalibur Ruby CCD diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.782, T max = 1.000

5738 measured reflections

2911 independent reflections

2319 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.116

S = 1.06

2911 reflections

234 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.14 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811021489/pk2322sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811021489/pk2322Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811021489/pk2322Isup3.cml

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

C14H14F3NO4	F(000) = 656
Mr = 317.26	Dx = 1.456 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2yn	Cell parameters from 2319 reflections
a = 9.6277 (4) Å	θ = 5.5–75.5°
b = 15.9760 (6) Å	µ = 1.15 mm−1
c = 9.9738 (4) Å	T = 293 K
β = 109.314 (5)°	Block, colourless
V = 1447.75 (10) Å3	0.55 × 0.45 × 0.40 mm
Z = 4

Oxford Diffraction Xcalibur Ruby CCD diffractometer	2911 independent reflections
Radiation source: fine-focus sealed tube	2319 reflections with I > 2σ(I)
graphite	Rint = 0.018
Detector resolution: 10.2576 pixels mm-1	θmax = 75.9°, θmin = 5.5°
ω scans	h = −11→12
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −19→13
Tmin = 0.782, Tmax = 1.000	l = −12→12
5738 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.116	w = 1/[σ2(Fo2) + (0.0607P)2 + 0.1918P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
2911 reflections	Δρmax = 0.20 e Å−3
234 parameters	Δρmin = −0.14 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0092 (10)

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.Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.24919 (15)	0.21987 (8)	0.04081 (14)	0.0900 (4)
F2	0.24512 (15)	0.09413 (9)	−0.03770 (13)	0.0863 (4)
F3	0.42514 (12)	0.13538 (8)	0.14198 (14)	0.0805 (4)
O1	−0.16538 (14)	0.08409 (10)	0.51949 (16)	0.0773 (4)
O2	0.04297 (12)	0.12631 (7)	0.09810 (13)	0.0566 (3)
O3	0.12118 (13)	−0.03385 (7)	0.13702 (13)	0.0622 (3)
O4	0.34902 (11)	−0.00327 (7)	0.27903 (12)	0.0535 (3)
N1	0.34543 (16)	0.23072 (9)	0.50886 (17)	0.0590 (4)
C1	0.22216 (17)	0.19773 (10)	0.53026 (18)	0.0524 (4)
C2	0.1720 (2)	0.20300 (11)	0.6458 (2)	0.0627 (5)
C3	0.0439 (2)	0.16245 (13)	0.6367 (2)	0.0658 (5)
C4	−0.03659 (18)	0.11812 (11)	0.5139 (2)	0.0596 (4)
C5	0.01333 (17)	0.11079 (10)	0.40028 (19)	0.0528 (4)
C6	0.14673 (16)	0.15055 (9)	0.40867 (17)	0.0476 (4)
C7	0.23112 (16)	0.15638 (9)	0.31430 (17)	0.0479 (4)
C8	0.34965 (18)	0.20619 (10)	0.3800 (2)	0.0556 (4)
C9	0.19239 (16)	0.11127 (9)	0.17494 (17)	0.0475 (4)
C10	0.21565 (15)	0.01523 (9)	0.19510 (16)	0.0461 (4)
C11	0.3900 (2)	−0.09195 (11)	0.2897 (2)	0.0639 (5)
C12	0.4403 (3)	−0.11618 (14)	0.1696 (3)	0.0826 (6)
H12A	0.4697	−0.1739	0.1794	0.124*
H12B	0.5223	−0.0818	0.1702	0.124*
H12C	0.3613	−0.1085	0.0817	0.124*
C13	0.2798 (2)	0.14066 (12)	0.0805 (2)	0.0645 (5)
C14	−0.2605 (2)	0.04673 (16)	0.3932 (2)	0.0810 (6)
H14A	−0.3506	0.0303	0.4073	0.122*
H14B	−0.2137	−0.0017	0.3703	0.122*
H14C	−0.2815	0.0863	0.3166	0.122*
H1A	0.403 (2)	0.2684 (13)	0.559 (2)	0.066 (6)*
H2A	0.222 (2)	0.2317 (15)	0.724 (2)	0.079 (6)*
H2B	0.009 (2)	0.0882 (16)	0.045 (2)	0.079 (7)*
H3A	0.007 (2)	0.1646 (14)	0.715 (2)	0.075 (6)*
H5A	−0.0408 (19)	0.0778 (12)	0.3176 (19)	0.056 (5)*
H8A	0.430 (2)	0.2217 (12)	0.3467 (19)	0.059 (5)*
H11A	0.304 (2)	−0.1242 (13)	0.292 (2)	0.068 (6)*
H11B	0.473 (3)	−0.0959 (14)	0.378 (2)	0.079 (6)*

	U11	U22	U33	U12	U13	U23
F1	0.1020 (9)	0.0653 (7)	0.0962 (9)	−0.0066 (6)	0.0240 (7)	0.0318 (6)
F2	0.0997 (9)	0.0956 (10)	0.0691 (7)	−0.0147 (7)	0.0352 (6)	−0.0033 (6)
F3	0.0560 (6)	0.0923 (9)	0.0963 (8)	−0.0088 (6)	0.0292 (6)	0.0143 (7)
O1	0.0549 (7)	0.0862 (10)	0.0964 (10)	−0.0112 (7)	0.0323 (7)	−0.0175 (8)
O2	0.0429 (6)	0.0470 (6)	0.0639 (7)	0.0081 (5)	−0.0037 (5)	−0.0038 (6)
O3	0.0518 (6)	0.0471 (6)	0.0710 (7)	−0.0071 (5)	−0.0022 (5)	0.0011 (5)
O4	0.0387 (5)	0.0429 (6)	0.0696 (7)	0.0059 (4)	0.0053 (5)	0.0037 (5)
N1	0.0492 (7)	0.0435 (7)	0.0687 (9)	−0.0106 (6)	−0.0014 (7)	−0.0051 (6)
C1	0.0448 (8)	0.0369 (7)	0.0645 (10)	0.0019 (6)	0.0032 (7)	−0.0040 (7)
C2	0.0611 (10)	0.0519 (10)	0.0645 (11)	0.0052 (8)	0.0066 (9)	−0.0157 (8)
C3	0.0611 (10)	0.0628 (11)	0.0724 (12)	0.0074 (9)	0.0204 (9)	−0.0139 (9)
C4	0.0469 (8)	0.0525 (9)	0.0774 (11)	0.0031 (7)	0.0179 (8)	−0.0085 (8)
C5	0.0420 (8)	0.0442 (8)	0.0648 (10)	−0.0021 (6)	0.0076 (7)	−0.0100 (7)
C6	0.0408 (7)	0.0331 (7)	0.0600 (9)	0.0026 (6)	0.0049 (6)	−0.0033 (6)
C7	0.0404 (7)	0.0358 (7)	0.0594 (9)	0.0005 (6)	0.0055 (6)	0.0032 (6)
C8	0.0437 (8)	0.0459 (9)	0.0673 (10)	−0.0053 (7)	0.0050 (7)	0.0068 (7)
C9	0.0365 (7)	0.0415 (8)	0.0563 (9)	0.0015 (6)	0.0042 (6)	0.0038 (6)
C10	0.0390 (7)	0.0426 (8)	0.0515 (8)	0.0001 (6)	0.0079 (6)	0.0010 (6)
C11	0.0521 (9)	0.0459 (9)	0.0860 (13)	0.0096 (8)	0.0125 (9)	0.0074 (9)
C12	0.0726 (13)	0.0660 (12)	0.1059 (17)	0.0106 (10)	0.0249 (12)	−0.0157 (12)
C13	0.0636 (10)	0.0580 (10)	0.0664 (11)	−0.0046 (8)	0.0139 (8)	0.0111 (9)
C14	0.0487 (10)	0.0883 (15)	0.1008 (16)	−0.0144 (10)	0.0176 (10)	−0.0043 (12)

F1—C13	1.330 (2)	C4—C5	1.375 (3)
F2—C13	1.339 (2)	C5—C6	1.410 (2)
F3—C13	1.332 (2)	C5—H5A	0.972 (18)
O1—C4	1.372 (2)	C6—C7	1.436 (2)
O1—C14	1.421 (3)	C7—C8	1.367 (2)
O2—C9	1.4090 (17)	C7—C9	1.499 (2)
O2—H2B	0.80 (2)	C8—H8A	0.974 (18)
O3—C10	1.1954 (18)	C9—C13	1.530 (3)
O4—C10	1.3137 (17)	C9—C10	1.554 (2)
O4—C11	1.465 (2)	C11—C12	1.484 (3)
N1—C8	1.357 (2)	C11—H11A	0.98 (2)
N1—C1	1.378 (2)	C11—H11B	0.98 (2)
N1—H1A	0.86 (2)	C12—H12A	0.9600
C1—C2	1.391 (3)	C12—H12B	0.9600
C1—C6	1.408 (2)	C12—H12C	0.9600
C2—C3	1.369 (3)	C14—H14A	0.9600
C2—H2A	0.90 (2)	C14—H14B	0.9600
C3—C4	1.405 (3)	C14—H14C	0.9600
C3—H3A	0.97 (2)
C4—O1—C14	117.18 (16)	C7—C9—C13	113.86 (13)
C9—O2—H2B	110.4 (17)	O2—C9—C10	108.44 (12)
C10—O4—C11	116.54 (13)	C7—C9—C10	111.95 (13)
C8—N1—C1	109.48 (14)	C13—C9—C10	107.31 (14)
C8—N1—H1A	122.4 (13)	O3—C10—O4	126.01 (14)
C1—N1—H1A	127.1 (13)	O3—C10—C9	122.07 (13)
N1—C1—C2	131.13 (16)	O4—C10—C9	111.91 (12)
N1—C1—C6	107.25 (16)	O4—C11—C12	110.23 (17)
C2—C1—C6	121.60 (16)	O4—C11—H11A	107.4 (12)
C3—C2—C1	117.93 (17)	C12—C11—H11A	112.8 (12)
C3—C2—H2A	120.9 (14)	O4—C11—H11B	104.3 (13)
C1—C2—H2A	121.2 (14)	C12—C11—H11B	109.3 (13)
C2—C3—C4	121.43 (19)	H11A—C11—H11B	112.5 (17)
C2—C3—H3A	119.9 (13)	C11—C12—H12A	109.5
C4—C3—H3A	118.6 (13)	C11—C12—H12B	109.5
O1—C4—C5	124.53 (16)	H12A—C12—H12B	109.5
O1—C4—C3	114.21 (18)	C11—C12—H12C	109.5
C5—C4—C3	121.26 (17)	H12A—C12—H12C	109.5
C4—C5—C6	118.20 (15)	H12B—C12—H12C	109.5
C4—C5—H5A	120.7 (11)	F1—C13—F3	107.05 (16)
C6—C5—H5A	121.1 (11)	F1—C13—F2	107.46 (16)
C1—C6—C5	119.49 (16)	F3—C13—F2	106.77 (17)
C1—C6—C7	106.70 (14)	F1—C13—C9	111.24 (17)
C5—C6—C7	133.81 (15)	F3—C13—C9	113.91 (15)
C8—C7—C6	106.71 (15)	F2—C13—C9	110.11 (15)
C8—C7—C9	129.49 (16)	O1—C14—H14A	109.5
C6—C7—C9	123.74 (13)	O1—C14—H14B	109.5
N1—C8—C7	109.86 (16)	H14A—C14—H14B	109.5
N1—C8—H8A	121.8 (11)	O1—C14—H14C	109.5
C7—C8—H8A	128.3 (11)	H14A—C14—H14C	109.5
O2—C9—C7	108.57 (13)	H14B—C14—H14C	109.5
O2—C9—C13	106.46 (13)
C8—N1—C1—C2	178.10 (17)	C8—C7—C9—O2	−133.00 (17)
C8—N1—C1—C6	0.03 (18)	C6—C7—C9—O2	50.01 (18)
N1—C1—C2—C3	−179.49 (18)	C8—C7—C9—C13	−14.6 (2)
C6—C1—C2—C3	−1.7 (3)	C6—C7—C9—C13	168.40 (14)
C1—C2—C3—C4	−1.2 (3)	C8—C7—C9—C10	107.32 (18)
C14—O1—C4—C5	−7.2 (3)	C6—C7—C9—C10	−69.67 (18)
C14—O1—C4—C3	172.94 (18)	C11—O4—C10—O3	7.0 (3)
C2—C3—C4—O1	−177.34 (18)	C11—O4—C10—C9	−171.67 (15)
C2—C3—C4—C5	2.8 (3)	O2—C9—C10—O3	8.1 (2)
O1—C4—C5—C6	178.83 (16)	C7—C9—C10—O3	127.84 (17)
C3—C4—C5—C6	−1.3 (3)	C13—C9—C10—O3	−106.54 (18)
N1—C1—C6—C5	−178.63 (14)	O2—C9—C10—O4	−173.15 (13)
C2—C1—C6—C5	3.1 (2)	C7—C9—C10—O4	−53.40 (18)
N1—C1—C6—C7	0.41 (17)	C13—C9—C10—O4	72.22 (17)
C2—C1—C6—C7	−177.88 (14)	C10—O4—C11—C12	83.2 (2)
C4—C5—C6—C1	−1.5 (2)	O2—C9—C13—F1	54.98 (18)
C4—C5—C6—C7	179.74 (16)	C7—C9—C13—F1	−64.61 (19)
C1—C6—C7—C8	−0.69 (17)	C10—C9—C13—F1	170.92 (14)
C5—C6—C7—C8	178.15 (17)	O2—C9—C13—F3	176.06 (15)
C1—C6—C7—C9	176.89 (13)	C7—C9—C13—F3	56.5 (2)
C5—C6—C7—C9	−4.3 (3)	C10—C9—C13—F3	−67.99 (19)
C1—N1—C8—C7	−0.48 (19)	O2—C9—C13—F2	−64.04 (18)
C6—C7—C8—N1	0.73 (18)	C7—C9—C13—F2	176.37 (13)
C9—C7—C8—N1	−176.66 (14)	C10—C9—C13—F2	51.91 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2i	0.86 (2)	2.11 (2)	2.9166 (18)	156.8 (18)
O2—H2B···O3ii	0.80 (2)	2.03 (2)	2.7798 (17)	156 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.86 (2)	2.11 (2)	2.9166 (18)	156.8 (18)
O2—H2B⋯O3ii	0.80 (2)	2.03 (2)	2.7798 (17)	156 (2)

Symmetry codes: (i) ; (ii) .