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The title dimethyl sulfoxide (DMSO) solvate, C8H4FNO2·C2H6OS, was isolated during a manual crystallization screen on 7-fluoro­isatin (7-fluoro­indoline-2,3-dione). Mol­ecules of 7-fluoro­isatin are linked via C—H...O inter­actions to form chains parallel to the a direction, from which N—H...O hydrogen-bonded mol­ecules of DMSO protrude.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680703526X/tk2182sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680703526X/tk2182Isup2.hkl
Contains datablock I

CCDC reference: 657818

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.031
  • wR factor = 0.085
  • Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT432_ALERT_2_B Short Inter X...Y Contact O3 .. C1 .. 2.87 Ang.
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.94 PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C1 - C2 ... 1.56 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact O3 .. C2 .. 2.93 Ang.
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.943 Tmax scaled 0.943 Tmin scaled 0.836
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

The title solvate, (I), (Figure 1) was isolated during a manual crystallization screen on 7-fluoroisatin. The crystallization screen was motivated by a wider investigation into the potential polymorphism displayed by the isomeric compounds 7-fluoroisatin and 5-fluoroisatin (Shankland et al., 2007; Mohamed et al., 2007a,b).

In the crystal structure of (I), chains of 7-fluoroisatin are formed by C—H···O interactions and each 7-fluoroisatin is linked to a DMSO molecule via a N—H···O hydrogen bond. Two identical chains form ribbons by the interdigitation of the DMSO molecules (Figure 2 and Table 1). The C—H···O interactions for this compound occur using O1 (i.e. the O adjacent to the N position) whereas the chain formed by 5-fluoroisatin DMSO (Mohamed et al., 2007a) uses O2. On viewing down the c axis, these ribbons can be seen to form planes parallel to (1 - 1 0) with separations of 2.36 Å and 3.40 Å where the DMSO molecules interdigitate (Figure 3).

Related literature top

7-Fluoroisatin is reported to be a suitable starting material for the preparation of 7-substituted-2-indolinones, a class of compounds which are understood to display anti-convulsant activity in animals (Canas-Rodriguez & Leeming, 1972). The 1,4-dioxane solvate of 7-fluoroisatin (Shankland et al., 2007) and the DMSO solvate of 5-fluoroisatin (Mohamed et al., 2007a) have also been prepared, as well as the oxindole derivative of 5-fluoroisatin (Mohamed et al., 2007b).

Experimental top

Single crystals of the title compound were crystallized from a saturated dimethyl sulfoxide solution by slow evaporation at 298 K over the course of four months.

Refinement top

Methyl-H atoms were located from the difference map and refined using a rigid rotor model with C—H = 0.98 Å, and with Uiso(H) = 1.5Ueq(C). All other H atoms were geometrically placed and refined using a riding model with C—H = 0.95 Å and N—H = 0.88 Å, and with Uiso(H) = 1.20 Ueq(C, N). The three reflections with the greatest discrepancies were omitted from the refinement.

Structure description top

The title solvate, (I), (Figure 1) was isolated during a manual crystallization screen on 7-fluoroisatin. The crystallization screen was motivated by a wider investigation into the potential polymorphism displayed by the isomeric compounds 7-fluoroisatin and 5-fluoroisatin (Shankland et al., 2007; Mohamed et al., 2007a,b).

In the crystal structure of (I), chains of 7-fluoroisatin are formed by C—H···O interactions and each 7-fluoroisatin is linked to a DMSO molecule via a N—H···O hydrogen bond. Two identical chains form ribbons by the interdigitation of the DMSO molecules (Figure 2 and Table 1). The C—H···O interactions for this compound occur using O1 (i.e. the O adjacent to the N position) whereas the chain formed by 5-fluoroisatin DMSO (Mohamed et al., 2007a) uses O2. On viewing down the c axis, these ribbons can be seen to form planes parallel to (1 - 1 0) with separations of 2.36 Å and 3.40 Å where the DMSO molecules interdigitate (Figure 3).

7-Fluoroisatin is reported to be a suitable starting material for the preparation of 7-substituted-2-indolinones, a class of compounds which are understood to display anti-convulsant activity in animals (Canas-Rodriguez & Leeming, 1972). The 1,4-dioxane solvate of 7-fluoroisatin (Shankland et al., 2007) and the DMSO solvate of 5-fluoroisatin (Mohamed et al., 2007a) have also been prepared, as well as the oxindole derivative of 5-fluoroisatin (Mohamed et al., 2007b).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 and PLATON (Spek 2003).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of (I) showing the numbering scheme used. Displacement ellipsoids are drawn at the 50% probability level and hydrogen atoms have been omitted for clarity.
[Figure 2] Fig. 2. The ribbon formed by 7-fluoroisatin and DMSO in (I) showing the hydrogen bonding interactions as blue dotted lines. Colour code: C - dark grey, H - light grey, N - blue, O - red, F - green, S - yellow.
[Figure 3] Fig. 3. Packing diagram showing the stacking of the ribbons in (I). Colour code: C - dark grey, H - light grey, N - blue, O - red, F - green, S - yellow.
7-fluoroindoline-2,3-dione–dimethyl sulfoxide (1/1) top
Crystal data top
C10H10FNO3SZ = 2
Mr = 243.25F(000) = 252
Triclinic, P1Dx = 1.513 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.4917 (12) ÅCell parameters from 3848 reflections
b = 8.4911 (14) Åθ = 2.4–28.3°
c = 8.9542 (15) ŵ = 0.31 mm1
α = 106.207 (2)°T = 150 K
β = 98.648 (2)°Rhomboid block, orange
γ = 96.242 (3)°0.53 × 0.26 × 0.19 mm
V = 533.89 (15) Å3
Data collection top
Bruker SMART APEX
diffractometer
2439 independent reflections
Radiation source: fine-focus sealed tube2355 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
ω rotation with narrow frames scansθmax = 28.3°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 99
Tmin = 0.886, Tmax = 1.000k = 1011
4718 measured reflectionsl = 1111
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.031H-atom parameters constrained
wR(F2) = 0.085 w = 1/[σ2(Fo2) + (0.04P)2 + 0.2177P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.001
2436 reflectionsΔρmax = 0.37 e Å3
148 parametersΔρmin = 0.25 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.036 (6)
Crystal data top
C10H10FNO3Sγ = 96.242 (3)°
Mr = 243.25V = 533.89 (15) Å3
Triclinic, P1Z = 2
a = 7.4917 (12) ÅMo Kα radiation
b = 8.4911 (14) ŵ = 0.31 mm1
c = 8.9542 (15) ÅT = 150 K
α = 106.207 (2)°0.53 × 0.26 × 0.19 mm
β = 98.648 (2)°
Data collection top
Bruker SMART APEX
diffractometer
2439 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
2355 reflections with I > 2σ(I)
Tmin = 0.886, Tmax = 1.000Rint = 0.028
4718 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0310 restraints
wR(F2) = 0.085H-atom parameters constrained
S = 1.08Δρmax = 0.37 e Å3
2436 reflectionsΔρmin = 0.25 e Å3
148 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.48025 (17)0.24882 (16)0.36792 (14)0.0223 (3)
C20.33034 (17)0.10687 (15)0.37074 (14)0.0225 (3)
C30.33940 (16)0.12133 (15)0.53918 (14)0.0205 (2)
C40.24087 (18)0.03106 (16)0.61588 (17)0.0264 (3)
H4A0.14670.05880.55750.032*
C50.2834 (2)0.07534 (17)0.78007 (17)0.0290 (3)
H5A0.21680.01590.83490.035*
C60.42278 (19)0.20619 (17)0.86501 (15)0.0265 (3)
H6A0.45140.23540.97730.032*
C70.51927 (17)0.29330 (15)0.78552 (14)0.0215 (2)
C80.47933 (16)0.25344 (14)0.62275 (14)0.0185 (2)
N10.56176 (14)0.32541 (13)0.52209 (12)0.0208 (2)
H1A0.65340.40850.55390.025*
O10.51535 (14)0.28218 (13)0.25143 (11)0.0301 (2)
O20.23455 (14)0.00815 (12)0.25429 (11)0.0320 (2)
F10.65707 (11)0.41893 (10)0.86828 (9)0.0312 (2)
C91.0906 (2)0.46043 (18)0.75001 (16)0.0293 (3)
H9A0.99190.40390.78570.044*
H9B1.20190.48920.83150.044*
H9C1.11390.38670.65160.044*
C100.9842 (2)0.74243 (17)0.90954 (15)0.0302 (3)
H10A0.93340.84420.91030.045*
H10B1.09950.77010.98630.045*
H10C0.89720.66620.93810.045*
O30.83993 (12)0.59461 (11)0.60778 (10)0.0224 (2)
S11.02562 (4)0.64525 (4)0.71564 (3)0.02143 (12)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0228 (6)0.0253 (6)0.0189 (6)0.0085 (5)0.0023 (4)0.0060 (5)
C20.0230 (6)0.0207 (6)0.0213 (6)0.0072 (5)0.0003 (4)0.0032 (5)
C30.0210 (6)0.0184 (5)0.0208 (6)0.0053 (4)0.0016 (4)0.0040 (4)
C40.0238 (6)0.0210 (6)0.0336 (7)0.0016 (5)0.0054 (5)0.0074 (5)
C50.0332 (7)0.0267 (6)0.0324 (7)0.0049 (5)0.0131 (5)0.0134 (5)
C60.0332 (7)0.0289 (6)0.0204 (6)0.0096 (5)0.0077 (5)0.0092 (5)
C70.0226 (6)0.0211 (6)0.0186 (6)0.0035 (4)0.0012 (4)0.0040 (4)
C80.0194 (5)0.0183 (5)0.0182 (5)0.0054 (4)0.0026 (4)0.0059 (4)
N10.0216 (5)0.0227 (5)0.0173 (5)0.0006 (4)0.0019 (4)0.0066 (4)
O10.0332 (5)0.0411 (6)0.0196 (4)0.0103 (4)0.0059 (4)0.0126 (4)
O20.0350 (5)0.0264 (5)0.0246 (5)0.0042 (4)0.0070 (4)0.0016 (4)
F10.0330 (4)0.0338 (4)0.0188 (4)0.0061 (3)0.0036 (3)0.0038 (3)
C90.0341 (7)0.0335 (7)0.0249 (6)0.0150 (6)0.0060 (5)0.0124 (5)
C100.0391 (7)0.0267 (6)0.0197 (6)0.0048 (5)0.0008 (5)0.0024 (5)
O30.0201 (4)0.0250 (4)0.0195 (4)0.0013 (3)0.0012 (3)0.0060 (3)
S10.01927 (17)0.02451 (18)0.01990 (17)0.00010 (11)0.00060 (11)0.00866 (12)
Geometric parameters (Å, º) top
C1—O11.2118 (16)C7—F11.3572 (14)
C1—N11.3640 (16)C7—C81.3783 (17)
C1—C21.5640 (18)C8—N11.3999 (15)
C2—O21.2087 (15)N1—H1A0.8800
C2—C31.4692 (17)S1—O31.5122 (9)
C3—C41.3883 (18)S1—C91.7848 (14)
C3—C81.3990 (16)S1—C101.7914 (14)
C4—C51.389 (2)C9—H9A0.9800
C4—H4A0.9500C9—H9B0.9800
C5—C61.393 (2)C9—H9C0.9800
C5—H5A0.9500C10—H10A0.9800
C6—C71.3816 (18)C10—H10B0.9800
C6—H6A0.9500C10—H10C0.9800
O1—C1—N1127.72 (13)C7—C8—C3118.45 (11)
O1—C1—C2126.38 (12)C7—C8—N1129.33 (11)
N1—C1—C2105.91 (10)C3—C8—N1112.22 (10)
O2—C2—C3130.21 (13)C1—N1—C8110.58 (10)
O2—C2—C1124.66 (12)C1—N1—H1A124.7
C3—C2—C1105.10 (10)C8—N1—H1A124.7
C4—C3—C8121.77 (11)O3—S1—C9106.48 (6)
C4—C3—C2132.07 (12)O3—S1—C10105.88 (6)
C8—C3—C2106.16 (11)C9—S1—C1097.75 (6)
C3—C4—C5118.36 (12)S1—C9—H9A109.5
C3—C4—H4A120.8S1—C9—H9B109.5
C5—C4—H4A120.8H9A—C9—H9B109.5
C4—C5—C6120.58 (12)S1—C9—H9C109.5
C4—C5—H5A119.7H9A—C9—H9C109.5
C6—C5—H5A119.7H9B—C9—H9C109.5
C7—C6—C5119.82 (12)S1—C10—H10A109.5
C7—C6—H6A120.1S1—C10—H10B109.5
C5—C6—H6A120.1H10A—C10—H10B109.5
F1—C7—C8119.24 (11)S1—C10—H10C109.5
F1—C7—C6119.73 (11)H10A—C10—H10C109.5
C8—C7—C6121.02 (12)H10B—C10—H10C109.5
O1—C1—C2—O22.9 (2)C5—C6—C7—C80.33 (19)
N1—C1—C2—O2177.03 (12)F1—C7—C8—C3178.67 (10)
O1—C1—C2—C3178.51 (12)C6—C7—C8—C30.56 (18)
N1—C1—C2—C31.60 (12)F1—C7—C8—N10.18 (19)
O2—C2—C3—C41.6 (2)C6—C7—C8—N1179.41 (12)
C1—C2—C3—C4179.85 (13)C4—C3—C8—C70.20 (18)
O2—C2—C3—C8177.65 (13)C2—C3—C8—C7179.16 (10)
C1—C2—C3—C80.88 (12)C4—C3—C8—N1179.24 (11)
C8—C3—C4—C50.37 (19)C2—C3—C8—N10.12 (13)
C2—C3—C4—C5179.55 (13)O1—C1—N1—C8178.40 (12)
C3—C4—C5—C60.6 (2)C2—C1—N1—C81.72 (13)
C4—C5—C6—C70.3 (2)C7—C8—N1—C1179.85 (12)
C5—C6—C7—F1178.89 (12)C3—C8—N1—C11.25 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O30.881.892.7679 (14)175
C6—H6A···O1i0.952.343.2870 (17)175
Symmetry code: (i) x, y, z+1.

Experimental details

Crystal data
Chemical formulaC10H10FNO3S
Mr243.25
Crystal system, space groupTriclinic, P1
Temperature (K)150
a, b, c (Å)7.4917 (12), 8.4911 (14), 8.9542 (15)
α, β, γ (°)106.207 (2), 98.648 (2), 96.242 (3)
V3)533.89 (15)
Z2
Radiation typeMo Kα
µ (mm1)0.31
Crystal size (mm)0.53 × 0.26 × 0.19
Data collection
DiffractometerBruker SMART APEX
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.886, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
4718, 2439, 2355
Rint0.028
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.031, 0.085, 1.08
No. of reflections2436
No. of parameters148
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.37, 0.25

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000) and Mercury (Macrae et al., 2006), SHELXL97 and PLATON (Spek 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O30.881.892.7679 (14)175
C6—H6A···O1i0.952.343.2870 (17)175
Symmetry code: (i) x, y, z+1.
 

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