organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

5-(Tri­fluoro­meth­­oxy)isatin

aDepartment of Chemistry, University of the Free State, PO Box 339, Bloemfontein, 9301, South Africa
*Correspondence e-mail: schuttem@ufs.ac.za

(Received 17 September 2012; accepted 25 October 2012; online 28 November 2012)

The title compound [systematic name: 5-(trifluoro­meth­oxy)-1H-indole-2,3-dione], C9H4F3NO3, crystallized with two mol­ecules in the asymmetric unit. Inter­molecular N—H⋯O hydrogen bonds link the mol­ecules to form layers parallel to the ab plane. In addition, ππ stacking inter­actions 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[Schutte, M., Visser, H. G., Roodt, A. & Braband, H. (2012). Acta Cryst. E68, o777.]); Garden et al. (2006[Garden, S. J., Pinto, A. C., Wardell, J. L., Low, J. N. & Glidewell, C. (2006). Acta Cryst. C62, o321-o323.]); Goldschmidt & Llewellyn (1950[Goldschmidt, G. H. & Llewellyn, F. J. (1950). Acta Cryst. 3, 294-305.]); Frolova et al. (1988[Frolova, N. A., Kravtsov, V. Kh., Biyushkin, V. N., Chumakov, Yu. M., Bel'kova, O. N. & Malinovskii, T. I. (1988). Zh. Strukt. Khim. 29, 155-158.]); Wei et al. (2004[Wei, H.-X., Zhou, C., Ham, S., White, J. M. & Birney, D. M. (2004). Org. Lett. 6, 4289-4292.]); Palmer et al. (1987[Palmer, M. H., Blake, A. J. & Gould, R. O. (1987). Chem. Phys. 115, 219-227.]); Akkurt et al. (2006[Akkurt, M., Türktekin, S., Jarrahpour, A. A., Khalili, D. & Büyükgüngör, O. (2006). Acta Cryst. E62, o1575-o1577.]). For reaction kinetic data on similar structures, see: Schutte et al. (2011[Schutte, M., Kemp, G., Visser, H. G. & Roodt, A. (2011). Inorg. Chem. 50, 12486-12498.]).

[Scheme 1]

Experimental

Crystal data
  • C9H4F3NO3

  • Mr = 231.13

  • Monoclinic, P 21 /n

  • 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[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.152, Tmax = 0.394

  • 26198 measured reflections

  • 4428 independent reflections

  • 3513 reflections with I > 2σ(I)

  • Rint = 0.029

Refinement
  • R[F2 > 2σ(F2)] = 0.036

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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) x, y-1, z; (ii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iv) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: DIAMOND (Brandenburg & Putz, 2005[Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information


Comment top

5-(Trifluoromethoxy)isatin crystallized in the P21/n spacegroup and with two independent molecules in the asymmetric unit. The use of 5-(trifluormethoxy)isatin forms part of a current study, where water soluble O,O'-donor bidentate ligands are coordinated to the rhenium tricarbonyl core in order to study the reactivity and activation of these potential radiopharmaceutical compounds. Previous studies have shown that the O,O'-bidenate ligands activate the Re(I) core to a great extent and we would like to explore this further (Schutte et al. (2011). The isatin molecule also has a variety of biological activities. It can act as an anticonvulsant agent, it has sedative effects but can also cause anxiety. Palmer et al., 1987; Goldschmidt & Llewellyn, 1950; Wei et al., 2004; Frolova et al., 1988; Akkurt et al., 2006). Due to its diverse pharmacological properties, a lot of interest has been shown in the isatin molecule and its derivatives. All bond lengths and angles compare well to the structure of N-benzylisatin reported by Schutte et al. (2012). Five intermolecular hydrogen interactions are observed in the structure (C—H···O, N—H···O and C—H···F) as well as π-π stacking with a centroid to centroid distance of 3.721 (1) Å. The molecules pack in a head to head fashion in alternating layers with the benzyl ring overlapping with the next molecules' pyrrolidinedione ring and vice versa. The π-π stacking and the packing in the unit cell are illustrated in Figure 2. The planarity of the ring systems, N1—C11—C12—C13—C14—C15—C16—C17—C18 and N2—C21—C22—C23—C24—C25—C26—C27—C28, are illustrated by very small deviations of all the atoms from these planes, with the largest deviations 0.023 (1) Å for N1 and 0.025 (1) for N2 respectively.

Related literature top

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 top

5-(Trifluoromethoxy)isatin was dissolved in water (pH 4). The crystls were grown from a vapour diffusion setup with chloroform at 5 °C in a commercial refrigerator.

Refinement top

Aromatic H atoms were positioned geometrically and allowed to ride on their parent atoms, with Uiso(H) = 1.2 Ueq(parent) and with a C—H distance of 0.93 Å. N-bound hydrogen atoms were placed from the electron density map and refined freely. 10 reflections with large negative intensities [I < –4σ(I)] were excluded from the refinement.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT-Plus (Bruker, 2008); data reduction: SAINT-Plus (Bruker, 2008); 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).

Figures top
[Figure 1] Fig. 1. Representation of the title compound, showing the numbering scheme and displacement ellipsoids (50% probability).
[Figure 2] Fig. 2. Observed π-π stacking (indicated by dashed lines) and packing in the crystal structure (hydrogen atoms omitted for clarity).
5-(trifluoromethoxy)-1H-indole-2,3-dione top
Crystal data top
C9H4F3NO3F(000) = 928
Mr = 231.13Dx = 1.728 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71069 Å
a = 14.329 (5) ÅCell parameters from 9825 reflections
b = 6.082 (5) Åθ = 2.8–28.2°
c = 20.401 (5) ŵ = 0.17 mm1
β = 91.608 (5)°T = 100 K
V = 1777.2 (16) Å3Needle, orange
Z = 80.51 × 0.18 × 0.10 mm
Data collection top
Bruker APEXII CCD
diffractometer
3513 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
ϕ and ω scansθmax = 28.3°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
h = 1919
Tmin = 0.152, Tmax = 0.394k = 78
26198 measured reflectionsl = 2727
4428 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102H 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 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.33 e Å3
Crystal data top
C9H4F3NO3V = 1777.2 (16) Å3
Mr = 231.13Z = 8
Monoclinic, P21/nMo Kα radiation
a = 14.329 (5) ŵ = 0.17 mm1
b = 6.082 (5) ÅT = 100 K
c = 20.401 (5) Å0.51 × 0.18 × 0.10 mm
β = 91.608 (5)°
Data collection top
Bruker APEXII CCD
diffractometer
4428 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
3513 reflections with I > 2σ(I)
Tmin = 0.152, Tmax = 0.394Rint = 0.029
26198 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.102H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.34 e Å3
4418 reflectionsΔρmin = 0.33 e Å3
297 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O20.44882 (8)0.39123 (17)0.43829 (5)0.0258 (2)
O40.25592 (7)0.62417 (16)0.33404 (5)0.0222 (2)
O30.41251 (8)0.06479 (18)0.69260 (5)0.0255 (2)
O60.01035 (8)0.39384 (17)0.38480 (5)0.0258 (2)
N10.33820 (9)0.1165 (2)0.43057 (6)0.0207 (3)
F30.35956 (8)0.40475 (15)0.70118 (5)0.0375 (3)
O50.21790 (7)0.35661 (17)0.44843 (5)0.0230 (2)
F20.38339 (8)0.20705 (17)0.78654 (5)0.0366 (2)
F50.09269 (8)0.57440 (18)0.43734 (6)0.0482 (3)
O10.37037 (8)0.09137 (17)0.33911 (5)0.0241 (2)
N20.16708 (9)0.3571 (2)0.28133 (6)0.0202 (3)
C130.39620 (10)0.1071 (2)0.51369 (7)0.0188 (3)
C140.34985 (10)0.0899 (2)0.49875 (7)0.0196 (3)
C110.37229 (10)0.0574 (2)0.39792 (7)0.0202 (3)
C230.13214 (10)0.1310 (2)0.36813 (7)0.0184 (3)
F60.05978 (9)0.2481 (2)0.46963 (6)0.0564 (4)
C180.41720 (10)0.1665 (2)0.57812 (7)0.0202 (3)
H180.4490.29580.58850.024*
F10.26737 (7)0.1395 (2)0.72116 (5)0.0436 (3)
F40.13875 (8)0.2999 (2)0.38080 (7)0.0564 (4)
C150.32098 (11)0.2309 (2)0.54708 (8)0.0244 (3)
H150.28970.3610.53690.029*
C170.38837 (10)0.0232 (2)0.62607 (7)0.0217 (3)
C260.03648 (10)0.1692 (2)0.29098 (7)0.0221 (3)
H260.00380.27270.26590.027*
C240.12267 (10)0.1618 (2)0.30027 (7)0.0190 (3)
C210.20969 (10)0.4565 (2)0.33289 (7)0.0195 (3)
C280.09416 (10)0.0507 (2)0.39831 (7)0.0198 (3)
H280.1010.07340.44330.024*
C270.04544 (10)0.1968 (2)0.35822 (7)0.0209 (3)
C120.41347 (10)0.2177 (2)0.45094 (7)0.0196 (3)
C290.06921 (12)0.3765 (3)0.41759 (9)0.0324 (4)
C220.18838 (10)0.3137 (2)0.39389 (7)0.0182 (3)
C250.07594 (10)0.0119 (2)0.26051 (7)0.0217 (3)
H250.0710.03110.21530.026*
C190.35582 (11)0.2012 (3)0.72439 (7)0.0251 (3)
C160.34070 (11)0.1702 (2)0.61182 (8)0.0250 (3)
H160.32170.26020.64580.03*
H10.3123 (13)0.224 (3)0.4120 (9)0.028 (5)*
H20.1668 (14)0.403 (3)0.2399 (11)0.041 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.0326 (6)0.0228 (5)0.0219 (5)0.0080 (4)0.0022 (4)0.0025 (4)
O40.0266 (5)0.0198 (5)0.0204 (5)0.0040 (4)0.0004 (4)0.0013 (4)
O30.0346 (6)0.0267 (5)0.0150 (5)0.0069 (4)0.0031 (4)0.0020 (4)
O60.0279 (6)0.0206 (5)0.0291 (6)0.0038 (4)0.0033 (4)0.0012 (4)
N10.0249 (6)0.0178 (6)0.0193 (6)0.0031 (5)0.0038 (5)0.0016 (5)
F30.0583 (7)0.0238 (5)0.0308 (5)0.0088 (4)0.0079 (5)0.0058 (4)
O50.0240 (5)0.0285 (5)0.0165 (5)0.0019 (4)0.0021 (4)0.0034 (4)
F20.0518 (6)0.0408 (6)0.0171 (5)0.0045 (5)0.0000 (4)0.0003 (4)
F50.0507 (7)0.0394 (6)0.0552 (7)0.0198 (5)0.0141 (6)0.0074 (5)
O10.0310 (6)0.0246 (5)0.0166 (5)0.0014 (4)0.0024 (4)0.0000 (4)
N20.0259 (6)0.0198 (6)0.0147 (6)0.0021 (5)0.0011 (5)0.0005 (5)
C130.0205 (7)0.0176 (6)0.0183 (7)0.0003 (5)0.0016 (5)0.0016 (5)
C140.0205 (7)0.0189 (6)0.0192 (7)0.0006 (5)0.0022 (5)0.0001 (5)
C110.0207 (7)0.0195 (6)0.0203 (7)0.0005 (5)0.0020 (5)0.0012 (5)
C230.0194 (7)0.0192 (6)0.0165 (7)0.0011 (5)0.0008 (5)0.0029 (5)
F60.0623 (8)0.0617 (8)0.0470 (7)0.0306 (6)0.0310 (6)0.0241 (6)
C180.0219 (7)0.0194 (6)0.0192 (7)0.0003 (5)0.0023 (5)0.0002 (5)
F10.0322 (6)0.0599 (7)0.0391 (6)0.0086 (5)0.0089 (5)0.0075 (5)
F40.0260 (6)0.0664 (8)0.0766 (9)0.0006 (5)0.0004 (6)0.0168 (7)
C150.0283 (8)0.0179 (7)0.0269 (8)0.0025 (6)0.0004 (6)0.0020 (6)
C170.0264 (7)0.0229 (7)0.0157 (7)0.0047 (6)0.0018 (5)0.0015 (5)
C260.0215 (7)0.0206 (7)0.0241 (7)0.0003 (5)0.0013 (6)0.0057 (6)
C240.0199 (7)0.0187 (6)0.0183 (7)0.0017 (5)0.0000 (5)0.0006 (5)
C210.0207 (7)0.0195 (6)0.0182 (7)0.0018 (5)0.0007 (5)0.0020 (5)
C280.0211 (7)0.0210 (7)0.0175 (7)0.0009 (5)0.0002 (5)0.0010 (5)
C270.0203 (7)0.0178 (6)0.0247 (7)0.0001 (5)0.0028 (6)0.0006 (5)
C120.0201 (7)0.0204 (7)0.0181 (7)0.0004 (5)0.0027 (5)0.0001 (5)
C290.0317 (9)0.0316 (8)0.0340 (9)0.0095 (7)0.0050 (7)0.0019 (7)
C220.0183 (6)0.0189 (6)0.0173 (7)0.0019 (5)0.0008 (5)0.0019 (5)
C250.0240 (7)0.0232 (7)0.0178 (7)0.0000 (6)0.0023 (5)0.0027 (5)
C190.0300 (8)0.0260 (7)0.0193 (7)0.0010 (6)0.0015 (6)0.0043 (6)
C160.0316 (8)0.0203 (7)0.0233 (8)0.0015 (6)0.0028 (6)0.0069 (6)
Geometric parameters (Å, º) top
O2—C121.2017 (19)C11—C121.560 (2)
O4—C211.2157 (19)C23—C281.384 (2)
O3—C191.3410 (19)C23—C241.400 (2)
O3—C171.4140 (18)C23—C221.462 (2)
O6—C291.342 (2)F6—C291.322 (2)
O6—C271.4134 (19)C18—C171.382 (2)
N1—C111.349 (2)C18—H180.93
N1—C141.4055 (19)F1—C191.322 (2)
N1—H10.84 (2)F4—C291.316 (2)
F3—C191.327 (2)C15—C161.393 (2)
O5—C221.2078 (17)C15—H150.93
F2—C191.3180 (18)C17—C161.387 (2)
F5—C291.316 (2)C26—C271.384 (2)
O1—C111.2170 (18)C26—C251.393 (2)
N2—C211.3450 (18)C26—H260.93
N2—C241.407 (2)C24—C251.381 (2)
N2—H20.89 (2)C21—C221.555 (2)
C13—C181.388 (2)C28—C271.383 (2)
C13—C141.399 (2)C28—H280.93
C13—C121.473 (2)C25—H250.93
C14—C151.379 (2)C16—H160.93
C19—O3—C17116.08 (12)C23—C24—N2110.67 (12)
C29—O6—C27116.17 (12)O4—C21—N2128.85 (14)
C11—N1—C14111.35 (12)O4—C21—C22124.91 (13)
C11—N1—H1123.4 (13)N2—C21—C22106.24 (12)
C14—N1—H1125.2 (13)C27—C28—C23116.62 (13)
C21—N2—C24111.32 (12)C27—C28—H28121.7
C21—N2—H2126.2 (14)C23—C28—H28121.7
C24—N2—H2122.4 (14)C28—C27—C26122.61 (14)
C18—C13—C14121.22 (13)C28—C27—O6119.79 (13)
C18—C13—C12131.81 (13)C26—C27—O6117.33 (13)
C14—C13—C12106.98 (12)O2—C12—C13132.05 (13)
C15—C14—C13121.78 (14)O2—C12—C11123.61 (13)
C15—C14—N1127.34 (14)C13—C12—C11104.33 (12)
C13—C14—N1110.88 (12)F5—C29—F4107.62 (14)
O1—C11—N1128.44 (13)F5—C29—F6108.41 (15)
O1—C11—C12125.11 (13)F4—C29—F6107.90 (16)
N1—C11—C12106.43 (12)F5—C29—O6108.00 (14)
C28—C23—C24121.25 (13)F4—C29—O6112.56 (15)
C28—C23—C22131.81 (13)F6—C29—O6112.18 (14)
C24—C23—C22106.91 (12)O5—C22—C23132.15 (13)
C17—C18—C13116.42 (13)O5—C22—C21123.01 (13)
C17—C18—H18121.8C23—C22—C21104.81 (12)
C13—C18—H18121.8C24—C25—C26117.14 (14)
C14—C15—C16117.14 (14)C24—C25—H25121.4
C14—C15—H15121.4C26—C25—H25121.4
C16—C15—H15121.4F2—C19—F1108.46 (13)
C18—C17—C16122.79 (14)F2—C19—F3107.71 (13)
C18—C17—O3119.79 (13)F1—C19—F3107.18 (13)
C16—C17—O3117.31 (13)F2—C19—O3108.22 (13)
C27—C26—C25120.73 (13)F1—C19—O3113.15 (14)
C27—C26—H26119.6F3—C19—O3111.94 (13)
C25—C26—H26119.6C17—C16—C15120.63 (14)
C25—C24—C23121.63 (13)C17—C16—H16119.7
C25—C24—N2127.70 (13)C15—C16—H16119.7
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O4i0.84 (2)1.99 (2)2.7615 (18)152.8 (18)
N2—H2···O1ii0.89 (2)2.03 (2)2.8776 (18)157.4 (19)
N2—H2···O4iii0.89 (2)2.55 (2)2.9850 (18)111.2 (16)
C16—H16···F3i0.932.393.171 (2)142
C18—H18···O2iv0.932.473.327 (3)153
Symmetry codes: (i) x, y1, z; (ii) x+1/2, y+1/2, z+1/2; (iii) x+1/2, y1/2, z+1/2; (iv) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC9H4F3NO3
Mr231.13
Crystal system, space groupMonoclinic, P21/n
Temperature (K)100
a, b, c (Å)14.329 (5), 6.082 (5), 20.401 (5)
β (°) 91.608 (5)
V3)1777.2 (16)
Z8
Radiation typeMo Kα
µ (mm1)0.17
Crystal size (mm)0.51 × 0.18 × 0.10
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2008)
Tmin, Tmax0.152, 0.394
No. of measured, independent and
observed [I > 2σ(I)] reflections
26198, 4428, 3513
Rint0.029
(sin θ/λ)max1)0.668
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.102, 1.04
No. of reflections4418
No. of parameters297
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.34, 0.33

Computer programs: APEX2 (Bruker, 2008), SAINT-Plus (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O4i0.84 (2)1.99 (2)2.7615 (18)152.8 (18)
N2—H2···O1ii0.89 (2)2.03 (2)2.8776 (18)157.4 (19)
N2—H2···O4iii0.89 (2)2.55 (2)2.9850 (18)111.2 (16)
C16—H16···F3i0.932.393.171 (2)142.1
C18—H18···O2iv0.932.473.327 (3)152.9
Symmetry codes: (i) x, y1, z; (ii) x+1/2, y+1/2, z+1/2; (iii) x+1/2, y1/2, z+1/2; (iv) x+1, y+1, z+1.
 

Acknowledgements

The University of the Free State, the Chemistry Department, the NRF and SASOL Ltd are acknowledged for funding.

References

First citationAkkurt, M., Türktekin, S., Jarrahpour, A. A., Khalili, D. & Büyükgüngör, O. (2006). Acta Cryst. E62, o1575–o1577.  Web of Science CSD CrossRef IUCr Journals
First citationBrandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.
First citationBruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals
First citationFrolova, N. A., Kravtsov, V. Kh., Biyushkin, V. N., Chumakov, Yu. M., Bel'kova, O. N. & Malinovskii, T. I. (1988). Zh. Strukt. Khim. 29, 155–158.  CAS
First citationGarden, S. J., Pinto, A. C., Wardell, J. L., Low, J. N. & Glidewell, C. (2006). Acta Cryst. C62, o321–o323.  Web of Science CSD CrossRef CAS IUCr Journals
First citationGoldschmidt, G. H. & Llewellyn, F. J. (1950). Acta Cryst. 3, 294–305.  CSD CrossRef CAS IUCr Journals Web of Science
First citationPalmer, M. H., Blake, A. J. & Gould, R. O. (1987). Chem. Phys. 115, 219–227.  CSD CrossRef CAS Web of Science
First citationSchutte, M., Kemp, G., Visser, H. G. & Roodt, A. (2011). Inorg. Chem. 50, 12486–12498.  Web of Science CSD CrossRef CAS PubMed
First citationSchutte, M., Visser, H. G., Roodt, A. & Braband, H. (2012). Acta Cryst. E68, o777.  CSD CrossRef IUCr Journals
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationWei, H.-X., Zhou, C., Ham, S., White, J. M. & Birney, D. M. (2004). Org. Lett. 6, 4289–4292.  Web of Science CrossRef PubMed CAS

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds