5-(Trifluoro-meth-oxy)isatin.

THE TITLE COMPOUND [SYSTEMATIC NAME: 5-(trifluoro-meth-oxy)-1H-indole-2,3-dione], C9H4F3NO3, crystallized with two mol-ecules in the asymmetric unit. Inter-molecular N-H⋯O hydrogen bonds link the mol-ecules to form layers parallel to the ab plane. In addition, π-π stacking inter-actions are observed with a centroid-centroid distance of 3.721 (1) Å. The near planarity of the two isatin ring systems is illustrated by by the maximum deviations of 0.023 (1) and 0.025 (1) Å for the N atom in each case.

Related literature

For similar structures and background information on isatin as a biological agent, see Schutte et al. (2012 ▶); Garden et al. (2006 ▶); Goldschmidt & Llewellyn (1950 ▶); Frolova et al. (1988 ▶); Wei et al. (2004 ▶); Palmer et al. (1987 ▶); Akkurt et al. (2006 ▶). For reaction kinetic data on similar structures, see: Schutte et al. (2011 ▶).

Experimental

Crystal data

C9H4F3NO3

M = 231.13

Monoclinic,

a = 14.329 (5) Å

b = 6.082 (5) Å

c = 20.401 (5) Å

β = 91.608 (5)°

V = 1777.2 (16) Å3

Z = 8

Mo Kα radiation

μ = 0.17 mm−1

T = 100 K

0.51 × 0.18 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.152, T max = 0.394

26198 measured reflections

4428 independent reflections

3513 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.102

S = 1.04

4418 reflections

297 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT-Plus (Bruker, 2008 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812044297/fy2072sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812044297/fy2072Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812044297/fy2072Isup3.cml

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

C9H4F3NO3	F(000) = 928
Mr = 231.13	Dx = 1.728 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71069 Å
a = 14.329 (5) Å	Cell parameters from 9825 reflections
b = 6.082 (5) Å	θ = 2.8–28.2°
c = 20.401 (5) Å	µ = 0.17 mm−1
β = 91.608 (5)°	T = 100 K
V = 1777.2 (16) Å3	Needle, orange
Z = 8	0.51 × 0.18 × 0.10 mm

Bruker APEXII CCD diffractometer	3513 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
φ and ω scans	θmax = 28.3°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −19→19
Tmin = 0.152, Tmax = 0.394	k = −7→8
26198 measured reflections	l = −27→27
4428 independent 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0458P)2 + 0.9713P] where P = (Fo2 + 2Fc2)/3
4418 reflections	(Δ/σ)max = 0.001
297 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
O2	0.44882 (8)	0.39123 (17)	0.43829 (5)	0.0258 (2)
O4	0.25592 (7)	0.62417 (16)	0.33404 (5)	0.0222 (2)
O3	0.41251 (8)	0.06479 (18)	0.69260 (5)	0.0255 (2)
O6	0.01035 (8)	−0.39384 (17)	0.38480 (5)	0.0258 (2)
N1	0.33820 (9)	−0.1165 (2)	0.43057 (6)	0.0207 (3)
F3	0.35956 (8)	0.40475 (15)	0.70118 (5)	0.0375 (3)
O5	0.21790 (7)	0.35661 (17)	0.44843 (5)	0.0230 (2)
F2	0.38339 (8)	0.20705 (17)	0.78654 (5)	0.0366 (2)
F5	−0.09269 (8)	−0.57440 (18)	0.43734 (6)	0.0482 (3)
O1	0.37037 (8)	0.09137 (17)	0.33911 (5)	0.0241 (2)
N2	0.16708 (9)	0.3571 (2)	0.28133 (6)	0.0202 (3)
C13	0.39620 (10)	0.1071 (2)	0.51369 (7)	0.0188 (3)
C14	0.34985 (10)	−0.0899 (2)	0.49875 (7)	0.0196 (3)
C11	0.37229 (10)	0.0574 (2)	0.39792 (7)	0.0202 (3)
C23	0.13214 (10)	0.1310 (2)	0.36813 (7)	0.0184 (3)
F6	−0.05978 (9)	−0.2481 (2)	0.46963 (6)	0.0564 (4)
C18	0.41720 (10)	0.1665 (2)	0.57812 (7)	0.0202 (3)
H18	0.449	0.2958	0.5885	0.024*
F1	0.26737 (7)	0.1395 (2)	0.72116 (5)	0.0436 (3)
F4	−0.13875 (8)	−0.2999 (2)	0.38080 (7)	0.0564 (4)
C15	0.32098 (11)	−0.2309 (2)	0.54708 (8)	0.0244 (3)
H15	0.2897	−0.361	0.5369	0.029*
C17	0.38837 (10)	0.0232 (2)	0.62607 (7)	0.0217 (3)
C26	0.03648 (10)	−0.1692 (2)	0.29098 (7)	0.0221 (3)
H26	0.0038	−0.2727	0.2659	0.027*
C24	0.12267 (10)	0.1618 (2)	0.30027 (7)	0.0190 (3)
C21	0.20969 (10)	0.4565 (2)	0.33289 (7)	0.0195 (3)
C28	0.09416 (10)	−0.0507 (2)	0.39831 (7)	0.0198 (3)
H28	0.101	−0.0734	0.4433	0.024*
C27	0.04544 (10)	−0.1968 (2)	0.35822 (7)	0.0209 (3)
C12	0.41347 (10)	0.2177 (2)	0.45094 (7)	0.0196 (3)
C29	−0.06921 (12)	−0.3765 (3)	0.41759 (9)	0.0324 (4)
C22	0.18838 (10)	0.3137 (2)	0.39389 (7)	0.0182 (3)
C25	0.07594 (10)	0.0119 (2)	0.26051 (7)	0.0217 (3)
H25	0.071	0.0311	0.2153	0.026*
C19	0.35582 (11)	0.2012 (3)	0.72439 (7)	0.0251 (3)
C16	0.34070 (11)	−0.1702 (2)	0.61182 (8)	0.0250 (3)
H16	0.3217	−0.2602	0.6458	0.03*
H1	0.3123 (13)	−0.224 (3)	0.4120 (9)	0.028 (5)*
H2	0.1668 (14)	0.403 (3)	0.2399 (11)	0.041 (6)*

	U11	U22	U33	U12	U13	U23
O2	0.0326 (6)	0.0228 (5)	0.0219 (5)	−0.0080 (4)	−0.0022 (4)	0.0025 (4)
O4	0.0266 (5)	0.0198 (5)	0.0204 (5)	−0.0040 (4)	0.0004 (4)	−0.0013 (4)
O3	0.0346 (6)	0.0267 (5)	0.0150 (5)	0.0069 (4)	−0.0031 (4)	0.0020 (4)
O6	0.0279 (6)	0.0206 (5)	0.0291 (6)	−0.0038 (4)	0.0033 (4)	0.0012 (4)
N1	0.0249 (6)	0.0178 (6)	0.0193 (6)	−0.0031 (5)	−0.0038 (5)	−0.0016 (5)
F3	0.0583 (7)	0.0238 (5)	0.0308 (5)	0.0088 (4)	0.0079 (5)	0.0058 (4)
O5	0.0240 (5)	0.0285 (5)	0.0165 (5)	−0.0019 (4)	−0.0021 (4)	−0.0034 (4)
F2	0.0518 (6)	0.0408 (6)	0.0171 (5)	0.0045 (5)	0.0000 (4)	0.0003 (4)
F5	0.0507 (7)	0.0394 (6)	0.0552 (7)	−0.0198 (5)	0.0141 (6)	0.0074 (5)
O1	0.0310 (6)	0.0246 (5)	0.0166 (5)	−0.0014 (4)	−0.0024 (4)	0.0000 (4)
N2	0.0259 (6)	0.0198 (6)	0.0147 (6)	−0.0021 (5)	−0.0011 (5)	−0.0005 (5)
C13	0.0205 (7)	0.0176 (6)	0.0183 (7)	0.0003 (5)	−0.0016 (5)	0.0016 (5)
C14	0.0205 (7)	0.0189 (6)	0.0192 (7)	0.0006 (5)	−0.0022 (5)	0.0001 (5)
C11	0.0207 (7)	0.0195 (6)	0.0203 (7)	0.0005 (5)	−0.0020 (5)	−0.0012 (5)
C23	0.0194 (7)	0.0192 (6)	0.0165 (7)	0.0011 (5)	−0.0008 (5)	−0.0029 (5)
F6	0.0623 (8)	0.0617 (8)	0.0470 (7)	−0.0306 (6)	0.0310 (6)	−0.0241 (6)
C18	0.0219 (7)	0.0194 (6)	0.0192 (7)	0.0003 (5)	−0.0023 (5)	0.0002 (5)
F1	0.0322 (6)	0.0599 (7)	0.0391 (6)	−0.0086 (5)	0.0089 (5)	−0.0075 (5)
F4	0.0260 (6)	0.0664 (8)	0.0766 (9)	0.0006 (5)	0.0004 (6)	0.0168 (7)
C15	0.0283 (8)	0.0179 (7)	0.0269 (8)	−0.0025 (6)	−0.0004 (6)	0.0020 (6)
C17	0.0264 (7)	0.0229 (7)	0.0157 (7)	0.0047 (6)	−0.0018 (5)	0.0015 (5)
C26	0.0215 (7)	0.0206 (7)	0.0241 (7)	0.0003 (5)	−0.0013 (6)	−0.0057 (6)
C24	0.0199 (7)	0.0187 (6)	0.0183 (7)	0.0017 (5)	0.0000 (5)	−0.0006 (5)
C21	0.0207 (7)	0.0195 (6)	0.0182 (7)	0.0018 (5)	0.0007 (5)	−0.0020 (5)
C28	0.0211 (7)	0.0210 (7)	0.0175 (7)	0.0009 (5)	0.0002 (5)	−0.0010 (5)
C27	0.0203 (7)	0.0178 (6)	0.0247 (7)	−0.0001 (5)	0.0028 (6)	−0.0006 (5)
C12	0.0201 (7)	0.0204 (7)	0.0181 (7)	−0.0004 (5)	−0.0027 (5)	−0.0001 (5)
C29	0.0317 (9)	0.0316 (8)	0.0340 (9)	−0.0095 (7)	0.0050 (7)	−0.0019 (7)
C22	0.0183 (6)	0.0189 (6)	0.0173 (7)	0.0019 (5)	0.0008 (5)	−0.0019 (5)
C25	0.0240 (7)	0.0232 (7)	0.0178 (7)	0.0000 (6)	−0.0023 (5)	−0.0027 (5)
C19	0.0300 (8)	0.0260 (7)	0.0193 (7)	0.0010 (6)	0.0015 (6)	0.0043 (6)
C16	0.0316 (8)	0.0203 (7)	0.0233 (8)	0.0015 (6)	0.0028 (6)	0.0069 (6)

O2—C12	1.2017 (19)	C11—C12	1.560 (2)
O4—C21	1.2157 (19)	C23—C28	1.384 (2)
O3—C19	1.3410 (19)	C23—C24	1.400 (2)
O3—C17	1.4140 (18)	C23—C22	1.462 (2)
O6—C29	1.342 (2)	F6—C29	1.322 (2)
O6—C27	1.4134 (19)	C18—C17	1.382 (2)
N1—C11	1.349 (2)	C18—H18	0.93
N1—C14	1.4055 (19)	F1—C19	1.322 (2)
N1—H1	0.84 (2)	F4—C29	1.316 (2)
F3—C19	1.327 (2)	C15—C16	1.393 (2)
O5—C22	1.2078 (17)	C15—H15	0.93
F2—C19	1.3180 (18)	C17—C16	1.387 (2)
F5—C29	1.316 (2)	C26—C27	1.384 (2)
O1—C11	1.2170 (18)	C26—C25	1.393 (2)
N2—C21	1.3450 (18)	C26—H26	0.93
N2—C24	1.407 (2)	C24—C25	1.381 (2)
N2—H2	0.89 (2)	C21—C22	1.555 (2)
C13—C18	1.388 (2)	C28—C27	1.383 (2)
C13—C14	1.399 (2)	C28—H28	0.93
C13—C12	1.473 (2)	C25—H25	0.93
C14—C15	1.379 (2)	C16—H16	0.93
C19—O3—C17	116.08 (12)	C23—C24—N2	110.67 (12)
C29—O6—C27	116.17 (12)	O4—C21—N2	128.85 (14)
C11—N1—C14	111.35 (12)	O4—C21—C22	124.91 (13)
C11—N1—H1	123.4 (13)	N2—C21—C22	106.24 (12)
C14—N1—H1	125.2 (13)	C27—C28—C23	116.62 (13)
C21—N2—C24	111.32 (12)	C27—C28—H28	121.7
C21—N2—H2	126.2 (14)	C23—C28—H28	121.7
C24—N2—H2	122.4 (14)	C28—C27—C26	122.61 (14)
C18—C13—C14	121.22 (13)	C28—C27—O6	119.79 (13)
C18—C13—C12	131.81 (13)	C26—C27—O6	117.33 (13)
C14—C13—C12	106.98 (12)	O2—C12—C13	132.05 (13)
C15—C14—C13	121.78 (14)	O2—C12—C11	123.61 (13)
C15—C14—N1	127.34 (14)	C13—C12—C11	104.33 (12)
C13—C14—N1	110.88 (12)	F5—C29—F4	107.62 (14)
O1—C11—N1	128.44 (13)	F5—C29—F6	108.41 (15)
O1—C11—C12	125.11 (13)	F4—C29—F6	107.90 (16)
N1—C11—C12	106.43 (12)	F5—C29—O6	108.00 (14)
C28—C23—C24	121.25 (13)	F4—C29—O6	112.56 (15)
C28—C23—C22	131.81 (13)	F6—C29—O6	112.18 (14)
C24—C23—C22	106.91 (12)	O5—C22—C23	132.15 (13)
C17—C18—C13	116.42 (13)	O5—C22—C21	123.01 (13)
C17—C18—H18	121.8	C23—C22—C21	104.81 (12)
C13—C18—H18	121.8	C24—C25—C26	117.14 (14)
C14—C15—C16	117.14 (14)	C24—C25—H25	121.4
C14—C15—H15	121.4	C26—C25—H25	121.4
C16—C15—H15	121.4	F2—C19—F1	108.46 (13)
C18—C17—C16	122.79 (14)	F2—C19—F3	107.71 (13)
C18—C17—O3	119.79 (13)	F1—C19—F3	107.18 (13)
C16—C17—O3	117.31 (13)	F2—C19—O3	108.22 (13)
C27—C26—C25	120.73 (13)	F1—C19—O3	113.15 (14)
C27—C26—H26	119.6	F3—C19—O3	111.94 (13)
C25—C26—H26	119.6	C17—C16—C15	120.63 (14)
C25—C24—C23	121.63 (13)	C17—C16—H16	119.7
C25—C24—N2	127.70 (13)	C15—C16—H16	119.7

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4i	0.84 (2)	1.99 (2)	2.7615 (18)	152.8 (18)
N2—H2···O1ii	0.89 (2)	2.03 (2)	2.8776 (18)	157.4 (19)
N2—H2···O4iii	0.89 (2)	2.55 (2)	2.9850 (18)	111.2 (16)
C16—H16···F3i	0.93	2.39	3.171 (2)	142
C18—H18···O2iv	0.93	2.47	3.327 (3)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4i	0.84 (2)	1.99 (2)	2.7615 (18)	152.8 (18)
N2—H2⋯O1ii	0.89 (2)	2.03 (2)	2.8776 (18)	157.4 (19)
N2—H2⋯O4iii	0.89 (2)	2.55 (2)	2.9850 (18)	111.2 (16)
C16—H16⋯F3i	0.93	2.39	3.171 (2)	142
C18—H18⋯O2iv	0.93	2.47	3.327 (3)	153

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