Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807047083/ci2470sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807047083/ci2470Isup2.hkl |
CCDC reference: 631308
Key indicators
- Single-crystal X-ray study
- T = 193 K
- Mean (C-C) = 0.002 Å
- R factor = 0.045
- wR factor = 0.114
- Data-to-parameter ratio = 13.1
checkCIF/PLATON results
No syntax errors found
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.802 0.971 Tmin(prime) and Tmax expected: 0.942 0.971 RR(prime) = 0.851 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.85 PLAT230_ALERT_2_C Hirshfeld Test Diff for C4 - C17 .. 5.21 su PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C4 - C17 ... 1.42 Ang.
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C3 = ... S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 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 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The title compound was prepared by the reaction of isatin (1 mmol), malononitrile (1 mmol) and cyclohexane-1,3-dione (1 mmol) in water. The reaction was catalyzed by TEBA (triethylbenzylammonium chloride, 1 mmol). After stirring at 333 K for 3 h, the reaction mixture was cooled and washed with small amount ethanol. The crude product was filtered and single crystals of the title compound, suitable for X-ray diffraction, were obtained from N,N-dimethylformamide solution by slow evaporation (yield 88%; m.p. 573–575 K). Spectroscopic analysis: IR (KBr, ν, cm-1): 33372, 3287, 3133, 2955, 2191, 1698, 1613, 1466, 1350, 1211, 1011, 933, 764, 679 1H NMR (400 MHz, DMSO-d6): 10.39 (s, 1H, NH), 7.21 (br s, 2H, NH2), 7.13 (t, 1H, J = 7.6 Hz, ArH), 7.01(d, 1H, J = 7.6 Hz, ArH), 6.88 (t, 1H, J = 7.6 Hz, ArH), 6.77(d, 1H, J = 8.0 Hz, ArH), 2.63–2.67 (m, 2H, CH2), 2.30–2.37 (m, 2H, CH2), 1.90–1.93 (m, 2H, CH2).
H atoms were placed in the idealized positions and allowed to ride on their parent atoms, with N—H = 0.88 Å, C—H = 0.95–0.99 Å and Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C,N) for others.
The indole nucleus is a well known heterocycle (Da-Silva et al., 2001). Compounds carrying the indole moiety exhibit antibacterial and antifungal activities (Joshi & Chand, 1982). Spirooxindole ring systems are found in a number of alkaloids like horsifiline, spirotryprostatin and elacomine (Abdel-Rahman et al., 2004). As a part of our program devoted to the preparation of heterocyclic compounds involving indole derivatives (Zhu et al., 2007), we have synthesized a series of spirooxindoles via reactions of isatins together with malononitrile and cyclohexane-1,3-dione in water. We report here the crystal structure of the title compound.
In the title molecule (Fig.1), the atoms of the pyran ring (C1—C5/O1) are almost coplanar with the largest deviation being 0.029 (2) Å for atom C2. The five-membered ring of the dihydroindolone ring system adopts a twist conformation. The cyclohexene ring adopts a half-chair conformation, with atoms C7 and C8 deviating from the C1/C2/C6/C9 plane by -0.222 (3) and 0.453 (3) Å, respectively.
The N—H···O and N—H···N hydrogen bonds link the spirooxindole molecules into a chain along the b axis. The N,N-dimethylformamide solvent molecules are linked to the chain via N—H···O and C—H···O hydrogen bonds (Table 1 and Fig. 2).
For general background, see: Da-Silva et al. (2001); Joshi & Chand (1982); Abdel-Rahman et al. (2004); Zhu et al. (2007).
Data collection: CrystalClear (Rigaku/MSC, 2001); cell refinement: CrystalClear (Rigaku/MSC, 2001); data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
C17H13N3O3·C3H7NO | Z = 2 |
Mr = 380.40 | F(000) = 400 |
Triclinic, P1 | Dx = 1.368 Mg m−3 |
Hall symbol: -P 1 | Melting point = 573–575 K |
a = 7.1833 (14) Å | Mo Kα radiation, λ = 0.71070 Å |
b = 8.8173 (18) Å | Cell parameters from 3696 reflections |
c = 15.351 (3) Å | θ = 3.3–25.3° |
α = 77.907 (13)° | µ = 0.10 mm−1 |
β = 77.691 (13)° | T = 193 K |
γ = 81.392 (14)° | Block, colourless |
V = 923.3 (3) Å3 | 0.60 × 0.30 × 0.30 mm |
Rigaku Mercury diffractometer | 3358 independent reflections |
Radiation source: fine-focus sealed tube | 2961 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
Detector resolution: 7.31 pixels mm-1 | θmax = 25.4°, θmin = 3.3° |
ω scans | h = −8→8 |
Absorption correction: multi-scan (Jacobson, 1998) | k = −10→10 |
Tmin = 0.802, Tmax = 0.971 | l = −18→18 |
9034 measured 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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.114 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0535P)2 + 0.3215P] where P = (Fo2 + 2Fc2)/3 |
3358 reflections | (Δ/σ)max = 0.001 |
256 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
C17H13N3O3·C3H7NO | γ = 81.392 (14)° |
Mr = 380.40 | V = 923.3 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.1833 (14) Å | Mo Kα radiation |
b = 8.8173 (18) Å | µ = 0.10 mm−1 |
c = 15.351 (3) Å | T = 193 K |
α = 77.907 (13)° | 0.60 × 0.30 × 0.30 mm |
β = 77.691 (13)° |
Rigaku Mercury diffractometer | 3358 independent reflections |
Absorption correction: multi-scan (Jacobson, 1998) | 2961 reflections with I > 2σ(I) |
Tmin = 0.802, Tmax = 0.971 | Rint = 0.023 |
9034 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.114 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.23 e Å−3 |
3358 reflections | Δρmin = −0.29 e Å−3 |
256 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 | ||
O1 | 0.75602 (16) | 0.52904 (12) | −0.00607 (7) | 0.0249 (3) | |
O2 | 0.50301 (19) | 0.52756 (14) | 0.30435 (8) | 0.0367 (3) | |
O3 | 0.98417 (17) | 0.42893 (14) | 0.22839 (8) | 0.0293 (3) | |
O4 | −0.06193 (19) | 0.22731 (16) | 0.47536 (9) | 0.0418 (4) | |
N1 | 0.8164 (2) | 0.23025 (16) | 0.31563 (9) | 0.0254 (3) | |
H1 | 0.8864 | 0.1995 | 0.3580 | 0.030* | |
N2 | 0.9859 (2) | 0.00722 (18) | 0.10933 (11) | 0.0399 (4) | |
N3 | 0.9162 (2) | 0.33299 (16) | −0.07013 (9) | 0.0272 (3) | |
H3A | 0.9712 | 0.2370 | −0.0710 | 0.033* | |
H3B | 0.9163 | 0.4006 | −0.1212 | 0.033* | |
N4 | 0.1442 (2) | 0.31623 (18) | 0.54114 (10) | 0.0338 (4) | |
C1 | 0.6547 (2) | 0.59323 (18) | 0.06719 (11) | 0.0217 (4) | |
C2 | 0.6263 (2) | 0.51357 (18) | 0.15212 (11) | 0.0212 (4) | |
C3 | 0.7133 (2) | 0.34806 (18) | 0.17859 (11) | 0.0214 (4) | |
C4 | 0.8191 (2) | 0.28850 (18) | 0.09332 (11) | 0.0219 (4) | |
C5 | 0.8330 (2) | 0.37603 (18) | 0.00864 (11) | 0.0213 (4) | |
C6 | 0.5133 (2) | 0.59234 (19) | 0.22550 (11) | 0.0256 (4) | |
C7 | 0.4122 (3) | 0.7513 (2) | 0.19830 (12) | 0.0327 (4) | |
H7A | 0.3859 | 0.8074 | 0.2499 | 0.039* | |
H7B | 0.2877 | 0.7405 | 0.1836 | 0.039* | |
C8 | 0.5300 (3) | 0.8459 (2) | 0.11697 (13) | 0.0348 (4) | |
H8A | 0.6477 | 0.8673 | 0.1339 | 0.042* | |
H8B | 0.4553 | 0.9471 | 0.0987 | 0.042* | |
C9 | 0.5850 (2) | 0.75999 (19) | 0.03733 (11) | 0.0265 (4) | |
H9A | 0.4723 | 0.7661 | 0.0087 | 0.032* | |
H9B | 0.6868 | 0.8110 | −0.0086 | 0.032* | |
C10 | 0.8564 (2) | 0.34412 (18) | 0.24291 (11) | 0.0230 (4) | |
C11 | 0.6486 (2) | 0.16690 (19) | 0.31519 (11) | 0.0236 (4) | |
C12 | 0.5570 (3) | 0.0556 (2) | 0.38021 (12) | 0.0291 (4) | |
H12 | 0.6091 | 0.0065 | 0.4324 | 0.035* | |
C13 | 0.3851 (3) | 0.0174 (2) | 0.36679 (12) | 0.0312 (4) | |
H13 | 0.3189 | −0.0592 | 0.4105 | 0.037* | |
C14 | 0.3093 (2) | 0.0893 (2) | 0.29071 (12) | 0.0292 (4) | |
H14 | 0.1905 | 0.0632 | 0.2836 | 0.035* | |
C15 | 0.4053 (2) | 0.19930 (19) | 0.22472 (11) | 0.0252 (4) | |
H15 | 0.3544 | 0.2474 | 0.1721 | 0.030* | |
C16 | 0.5758 (2) | 0.23715 (18) | 0.23728 (11) | 0.0215 (4) | |
C17 | 0.9110 (2) | 0.1332 (2) | 0.10209 (11) | 0.0266 (4) | |
C18 | 0.0839 (3) | 0.2885 (2) | 0.47086 (12) | 0.0325 (4) | |
H18 | 0.1590 | 0.3182 | 0.4124 | 0.039* | |
C19 | 0.0350 (3) | 0.2783 (3) | 0.63242 (14) | 0.0517 (6) | |
H19A | −0.0873 | 0.2444 | 0.6299 | 0.077* | |
H19B | 0.0106 | 0.3708 | 0.6609 | 0.077* | |
H19C | 0.1079 | 0.1942 | 0.6681 | 0.077* | |
C20 | 0.3197 (3) | 0.3875 (3) | 0.52988 (16) | 0.0454 (5) | |
H20A | 0.3779 | 0.4090 | 0.4654 | 0.068* | |
H20B | 0.4093 | 0.3162 | 0.5634 | 0.068* | |
H20C | 0.2900 | 0.4853 | 0.5532 | 0.068* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0310 (6) | 0.0231 (6) | 0.0189 (6) | −0.0024 (5) | −0.0024 (5) | −0.0025 (5) |
O2 | 0.0511 (8) | 0.0345 (7) | 0.0211 (7) | 0.0021 (6) | −0.0031 (6) | −0.0063 (5) |
O3 | 0.0283 (6) | 0.0318 (7) | 0.0287 (7) | −0.0089 (5) | −0.0069 (5) | −0.0026 (5) |
O4 | 0.0434 (8) | 0.0536 (9) | 0.0340 (8) | −0.0151 (7) | −0.0133 (6) | −0.0074 (6) |
N1 | 0.0259 (7) | 0.0292 (8) | 0.0208 (7) | −0.0042 (6) | −0.0076 (6) | −0.0001 (6) |
N2 | 0.0497 (10) | 0.0302 (9) | 0.0351 (9) | 0.0039 (8) | −0.0022 (8) | −0.0071 (7) |
N3 | 0.0333 (8) | 0.0256 (7) | 0.0209 (7) | −0.0034 (6) | −0.0001 (6) | −0.0052 (6) |
N4 | 0.0357 (8) | 0.0396 (9) | 0.0281 (8) | −0.0114 (7) | −0.0049 (7) | −0.0070 (7) |
C1 | 0.0208 (8) | 0.0237 (8) | 0.0219 (8) | −0.0039 (6) | −0.0043 (6) | −0.0057 (6) |
C2 | 0.0214 (8) | 0.0211 (8) | 0.0221 (8) | −0.0027 (6) | −0.0052 (7) | −0.0051 (6) |
C3 | 0.0226 (8) | 0.0212 (8) | 0.0196 (8) | −0.0033 (7) | −0.0022 (6) | −0.0031 (6) |
C4 | 0.0221 (8) | 0.0226 (8) | 0.0208 (8) | −0.0026 (7) | −0.0025 (6) | −0.0048 (6) |
C5 | 0.0196 (8) | 0.0216 (8) | 0.0239 (9) | −0.0057 (6) | −0.0029 (6) | −0.0059 (7) |
C6 | 0.0273 (9) | 0.0263 (9) | 0.0241 (9) | −0.0035 (7) | −0.0041 (7) | −0.0069 (7) |
C7 | 0.0372 (10) | 0.0304 (10) | 0.0292 (10) | 0.0043 (8) | −0.0048 (8) | −0.0097 (8) |
C8 | 0.0466 (11) | 0.0217 (9) | 0.0353 (10) | 0.0013 (8) | −0.0097 (9) | −0.0053 (7) |
C9 | 0.0282 (9) | 0.0235 (9) | 0.0261 (9) | −0.0026 (7) | −0.0068 (7) | 0.0009 (7) |
C10 | 0.0228 (8) | 0.0236 (8) | 0.0214 (8) | −0.0004 (7) | −0.0021 (7) | −0.0052 (7) |
C11 | 0.0245 (8) | 0.0239 (8) | 0.0214 (9) | −0.0012 (7) | −0.0010 (7) | −0.0063 (7) |
C12 | 0.0351 (10) | 0.0273 (9) | 0.0210 (9) | −0.0029 (8) | −0.0017 (7) | −0.0002 (7) |
C13 | 0.0337 (10) | 0.0273 (9) | 0.0291 (10) | −0.0089 (8) | 0.0042 (8) | −0.0039 (7) |
C14 | 0.0242 (9) | 0.0302 (9) | 0.0343 (10) | −0.0063 (7) | 0.0006 (7) | −0.0125 (8) |
C15 | 0.0246 (8) | 0.0262 (9) | 0.0245 (9) | 0.0000 (7) | −0.0024 (7) | −0.0082 (7) |
C16 | 0.0234 (8) | 0.0198 (8) | 0.0194 (8) | −0.0006 (7) | −0.0006 (6) | −0.0042 (6) |
C17 | 0.0285 (9) | 0.0286 (10) | 0.0218 (9) | −0.0036 (8) | −0.0015 (7) | −0.0057 (7) |
C18 | 0.0370 (10) | 0.0337 (10) | 0.0264 (10) | −0.0039 (8) | −0.0054 (8) | −0.0050 (7) |
C19 | 0.0602 (14) | 0.0711 (16) | 0.0292 (11) | −0.0247 (12) | −0.0036 (10) | −0.0141 (10) |
C20 | 0.0410 (11) | 0.0483 (12) | 0.0520 (13) | −0.0158 (10) | −0.0110 (10) | −0.0109 (10) |
O1—C5 | 1.3708 (19) | C7—C8 | 1.515 (3) |
O1—C1 | 1.3818 (19) | C7—H7A | 0.99 |
O2—C6 | 1.217 (2) | C7—H7B | 0.99 |
O3—C10 | 1.224 (2) | C8—C9 | 1.522 (2) |
O4—C18 | 1.232 (2) | C8—H8A | 0.99 |
N1—C10 | 1.348 (2) | C8—H8B | 0.99 |
N1—C11 | 1.404 (2) | C9—H9A | 0.99 |
N1—H1 | 0.88 | C9—H9B | 0.99 |
N2—C17 | 1.154 (2) | C11—C12 | 1.377 (2) |
N3—C5 | 1.334 (2) | C11—C16 | 1.395 (2) |
N3—H3A | 0.88 | C12—C13 | 1.394 (3) |
N3—H3B | 0.88 | C12—H12 | 0.95 |
N4—C18 | 1.324 (2) | C13—C14 | 1.386 (3) |
N4—C19 | 1.451 (3) | C13—H13 | 0.95 |
N4—C20 | 1.453 (2) | C14—C15 | 1.390 (2) |
C1—C2 | 1.334 (2) | C14—H14 | 0.95 |
C1—C9 | 1.489 (2) | C15—C16 | 1.378 (2) |
C2—C6 | 1.476 (2) | C15—H15 | 0.95 |
C2—C3 | 1.507 (2) | C18—H18 | 0.95 |
C3—C16 | 1.512 (2) | C19—H19A | 0.98 |
C3—C4 | 1.520 (2) | C19—H19B | 0.98 |
C3—C10 | 1.562 (2) | C19—H19C | 0.98 |
C4—C5 | 1.358 (2) | C20—H20A | 0.98 |
C4—C17 | 1.421 (2) | C20—H20B | 0.98 |
C6—C7 | 1.499 (2) | C20—H20C | 0.98 |
C5—O1—C1 | 118.78 (12) | C1—C9—C8 | 111.18 (14) |
C10—N1—C11 | 111.37 (13) | C1—C9—H9A | 109.4 |
C10—N1—H1 | 124.3 | C8—C9—H9A | 109.4 |
C11—N1—H1 | 124.3 | C1—C9—H9B | 109.4 |
C5—N3—H3A | 120.0 | C8—C9—H9B | 109.4 |
C5—N3—H3B | 120.0 | H9A—C9—H9B | 108.0 |
H3A—N3—H3B | 120.0 | O3—C10—N1 | 126.42 (15) |
C18—N4—C19 | 120.87 (16) | O3—C10—C3 | 125.40 (14) |
C18—N4—C20 | 121.55 (16) | N1—C10—C3 | 108.17 (13) |
C19—N4—C20 | 117.58 (16) | C12—C11—C16 | 121.73 (16) |
C2—C1—O1 | 123.37 (14) | C12—C11—N1 | 128.21 (15) |
C2—C1—C9 | 126.10 (15) | C16—C11—N1 | 110.03 (14) |
O1—C1—C9 | 110.52 (13) | C11—C12—C13 | 117.63 (16) |
C1—C2—C6 | 119.15 (14) | C11—C12—H12 | 121.2 |
C1—C2—C3 | 123.28 (14) | C13—C12—H12 | 121.2 |
C6—C2—C3 | 117.47 (14) | C14—C13—C12 | 121.03 (16) |
C2—C3—C16 | 115.35 (13) | C14—C13—H13 | 119.5 |
C2—C3—C4 | 108.87 (13) | C12—C13—H13 | 119.5 |
C16—C3—C4 | 111.96 (13) | C13—C14—C15 | 120.71 (16) |
C2—C3—C10 | 109.40 (13) | C13—C14—H14 | 119.6 |
C16—C3—C10 | 101.15 (12) | C15—C14—H14 | 119.6 |
C4—C3—C10 | 109.80 (13) | C16—C15—C14 | 118.60 (16) |
C5—C4—C17 | 117.66 (15) | C16—C15—H15 | 120.7 |
C5—C4—C3 | 123.70 (14) | C14—C15—H15 | 120.7 |
C17—C4—C3 | 118.63 (14) | C15—C16—C11 | 120.26 (15) |
N3—C5—C4 | 128.14 (15) | C15—C16—C3 | 131.25 (15) |
N3—C5—O1 | 110.07 (13) | C11—C16—C3 | 108.49 (14) |
C4—C5—O1 | 121.79 (14) | N2—C17—C4 | 179.8 (2) |
O2—C6—C2 | 120.16 (15) | O4—C18—N4 | 125.09 (17) |
O2—C6—C7 | 122.53 (15) | O4—C18—H18 | 117.5 |
C2—C6—C7 | 117.30 (14) | N4—C18—H18 | 117.5 |
C6—C7—C8 | 111.72 (14) | N4—C19—H19A | 109.5 |
C6—C7—H7A | 109.3 | N4—C19—H19B | 109.5 |
C8—C7—H7A | 109.3 | H19A—C19—H19B | 109.5 |
C6—C7—H7B | 109.3 | N4—C19—H19C | 109.5 |
C8—C7—H7B | 109.3 | H19A—C19—H19C | 109.5 |
H7A—C7—H7B | 107.9 | H19B—C19—H19C | 109.5 |
C7—C8—C9 | 111.41 (14) | N4—C20—H20A | 109.5 |
C7—C8—H8A | 109.3 | N4—C20—H20B | 109.5 |
C9—C8—H8A | 109.3 | H20A—C20—H20B | 109.5 |
C7—C8—H8B | 109.3 | N4—C20—H20C | 109.5 |
C9—C8—H8B | 109.3 | H20A—C20—H20C | 109.5 |
H8A—C8—H8B | 108.0 | H20B—C20—H20C | 109.5 |
C5—O1—C1—C2 | −0.4 (2) | O1—C1—C9—C8 | −162.11 (14) |
C5—O1—C1—C9 | 179.39 (13) | C7—C8—C9—C1 | −45.1 (2) |
O1—C1—C2—C6 | −179.06 (14) | C11—N1—C10—O3 | 173.86 (15) |
C9—C1—C2—C6 | 1.1 (2) | C11—N1—C10—C3 | −7.13 (18) |
O1—C1—C2—C3 | 4.5 (2) | C2—C3—C10—O3 | −50.0 (2) |
C9—C1—C2—C3 | −175.34 (15) | C16—C3—C10—O3 | −172.14 (15) |
C1—C2—C3—C16 | −131.48 (16) | C4—C3—C10—O3 | 69.4 (2) |
C6—C2—C3—C16 | 52.0 (2) | C2—C3—C10—N1 | 130.99 (14) |
C1—C2—C3—C4 | −4.7 (2) | C16—C3—C10—N1 | 8.84 (16) |
C6—C2—C3—C4 | 178.81 (13) | C4—C3—C10—N1 | −109.59 (14) |
C1—C2—C3—C10 | 115.34 (17) | C10—N1—C11—C12 | −176.03 (16) |
C6—C2—C3—C10 | −61.19 (17) | C10—N1—C11—C16 | 2.15 (19) |
C2—C3—C4—C5 | 1.5 (2) | C16—C11—C12—C13 | −1.5 (2) |
C16—C3—C4—C5 | 130.23 (16) | N1—C11—C12—C13 | 176.47 (16) |
C10—C3—C4—C5 | −118.26 (17) | C11—C12—C13—C14 | −0.1 (3) |
C2—C3—C4—C17 | −179.28 (14) | C12—C13—C14—C15 | 1.4 (3) |
C16—C3—C4—C17 | −50.54 (19) | C13—C14—C15—C16 | −1.1 (2) |
C10—C3—C4—C17 | 60.97 (18) | C14—C15—C16—C11 | −0.5 (2) |
C17—C4—C5—N3 | 3.3 (3) | C14—C15—C16—C3 | 178.92 (15) |
C3—C4—C5—N3 | −177.44 (15) | C12—C11—C16—C15 | 1.9 (2) |
C17—C4—C5—O1 | −177.17 (14) | N1—C11—C16—C15 | −176.44 (14) |
C3—C4—C5—O1 | 2.1 (2) | C12—C11—C16—C3 | −177.70 (14) |
C1—O1—C5—N3 | 176.78 (13) | N1—C11—C16—C3 | 3.99 (18) |
C1—O1—C5—C4 | −2.8 (2) | C2—C3—C16—C15 | 55.1 (2) |
C1—C2—C6—O2 | −172.10 (16) | C4—C3—C16—C15 | −70.2 (2) |
C3—C2—C6—O2 | 4.6 (2) | C10—C3—C16—C15 | 172.96 (17) |
C1—C2—C6—C7 | 8.8 (2) | C2—C3—C16—C11 | −125.43 (15) |
C3—C2—C6—C7 | −174.53 (14) | C4—C3—C16—C11 | 109.32 (15) |
O2—C6—C7—C8 | 143.83 (18) | C10—C3—C16—C11 | −7.52 (16) |
C2—C6—C7—C8 | −37.1 (2) | C19—N4—C18—O4 | −1.7 (3) |
C6—C7—C8—C9 | 55.4 (2) | C20—N4—C18—O4 | 179.26 (18) |
C2—C1—C9—C8 | 17.7 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O4i | 0.88 | 1.99 | 2.767 (2) | 147 |
N3—H3A···N2ii | 0.88 | 2.31 | 3.130 (2) | 155 |
N3—H3B···O3iii | 0.88 | 2.06 | 2.897 (2) | 158 |
C20—H20A···O2 | 0.98 | 2.50 | 3.464 (3) | 167 |
Symmetry codes: (i) x+1, y, z; (ii) −x+2, −y, −z; (iii) −x+2, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C17H13N3O3·C3H7NO |
Mr | 380.40 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 193 |
a, b, c (Å) | 7.1833 (14), 8.8173 (18), 15.351 (3) |
α, β, γ (°) | 77.907 (13), 77.691 (13), 81.392 (14) |
V (Å3) | 923.3 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.60 × 0.30 × 0.30 |
Data collection | |
Diffractometer | Rigaku Mercury |
Absorption correction | Multi-scan (Jacobson, 1998) |
Tmin, Tmax | 0.802, 0.971 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9034, 3358, 2961 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.602 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.114, 1.09 |
No. of reflections | 3358 |
No. of parameters | 256 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.23, −0.29 |
Computer programs: CrystalClear (Rigaku/MSC, 2001), CrystalStructure (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O4i | 0.88 | 1.99 | 2.767 (2) | 147 |
N3—H3A···N2ii | 0.88 | 2.31 | 3.130 (2) | 155 |
N3—H3B···O3iii | 0.88 | 2.06 | 2.897 (2) | 158 |
C20—H20A···O2 | 0.98 | 2.50 | 3.464 (3) | 167 |
Symmetry codes: (i) x+1, y, z; (ii) −x+2, −y, −z; (iii) −x+2, −y+1, −z. |
The indole nucleus is a well known heterocycle (Da-Silva et al., 2001). Compounds carrying the indole moiety exhibit antibacterial and antifungal activities (Joshi & Chand, 1982). Spirooxindole ring systems are found in a number of alkaloids like horsifiline, spirotryprostatin and elacomine (Abdel-Rahman et al., 2004). As a part of our program devoted to the preparation of heterocyclic compounds involving indole derivatives (Zhu et al., 2007), we have synthesized a series of spirooxindoles via reactions of isatins together with malononitrile and cyclohexane-1,3-dione in water. We report here the crystal structure of the title compound.
In the title molecule (Fig.1), the atoms of the pyran ring (C1—C5/O1) are almost coplanar with the largest deviation being 0.029 (2) Å for atom C2. The five-membered ring of the dihydroindolone ring system adopts a twist conformation. The cyclohexene ring adopts a half-chair conformation, with atoms C7 and C8 deviating from the C1/C2/C6/C9 plane by -0.222 (3) and 0.453 (3) Å, respectively.
The N—H···O and N—H···N hydrogen bonds link the spirooxindole molecules into a chain along the b axis. The N,N-dimethylformamide solvent molecules are linked to the chain via N—H···O and C—H···O hydrogen bonds (Table 1 and Fig. 2).