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In the title compound, C16H16N2O5, the indoline and oxazole moieties are almost planar, while the five-membered ring in the indoline moiety is slightly distorted towards an envelope conformation. The only intramolecular C—H...O contact forms a six-membered ring. The crystal packing is stabilized by dipole–dipole and van der Waals forces.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803024206/cv6245sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803024206/cv6245Isup2.hkl
Contains datablock I

CCDC reference: 227026

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.036
  • wR factor = 0.103
  • Data-to-parameter ratio = 11.5

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.98
Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.80 mm PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.56 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.72 Ratio
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

Ethyl 1-acetyl-2'-methyl-2-oxo-4',5'-dihydro-1H-indoline- 3-spiro-5'-oxazole-4'-carboxylate top
Crystal data top
C16H16N2O5Z = 2
Mr = 316.31F(000) = 332
Triclinic, P1Dx = 1.357 Mg m3
a = 9.348 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.614 (2) ÅCell parameters from 3060 reflections
c = 9.872 (2) Åθ = 2.4–28.3°
α = 77.015 (4)°µ = 0.10 mm1
β = 63.933 (3)°T = 293 K
γ = 88.200 (4)°Block, colourless
V = 774.4 (3) Å30.80 × 0.30 × 0.20 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
2665 independent reflections
Radiation source: fine-focus sealed tube2290 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
Detector resolution: 8.33 pixels mm-1θmax = 25.0°, θmin = 2.4°
ω scansh = 1111
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
k = 1011
Tmin = 0.923, Tmax = 0.980l = 1111
3825 measured 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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0528P)2 + 0.1374P]
where P = (Fo2 + 2Fc2)/3
2665 reflections(Δ/σ)max < 0.001
231 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = 0.16 e Å3
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
O10.30739 (14)0.57549 (13)0.14506 (13)0.0592 (3)
O20.42104 (17)0.15219 (14)0.12144 (17)0.0745 (4)
O30.27378 (11)0.63940 (10)0.14496 (12)0.0444 (3)
O40.16134 (14)0.37897 (13)0.42009 (13)0.0600 (3)
O50.04497 (13)0.29579 (11)0.20439 (13)0.0495 (3)
N10.35867 (13)0.35248 (13)0.02983 (14)0.0407 (3)
N20.00556 (14)0.64982 (13)0.25250 (15)0.0449 (3)
C10.30131 (16)0.48861 (16)0.03393 (17)0.0403 (3)
C20.21875 (16)0.50624 (15)0.13327 (16)0.0378 (3)
C30.26257 (15)0.37856 (15)0.22084 (16)0.0376 (3)
C40.23698 (19)0.34449 (18)0.37334 (19)0.0486 (4)
C50.2924 (2)0.2187 (2)0.4264 (2)0.0580 (4)
C60.3726 (2)0.13138 (19)0.3278 (2)0.0594 (5)
C70.3992 (2)0.16460 (17)0.1742 (2)0.0509 (4)
C80.34167 (16)0.28908 (15)0.12318 (17)0.0391 (3)
C90.40784 (18)0.27915 (19)0.15106 (19)0.0506 (4)
C100.4419 (2)0.3643 (2)0.3084 (2)0.0682 (5)
H10A0.49460.30770.38270.102*
H10B0.50960.44840.33320.102*
H10C0.34350.39190.31130.102*
C110.13932 (17)0.70613 (15)0.22284 (17)0.0424 (3)
C120.1726 (2)0.83908 (18)0.2595 (2)0.0587 (5)
H12A0.07360.87370.32260.088*
H12B0.22920.91030.16500.088*
H12C0.23630.81940.31480.088*
C130.03618 (16)0.52730 (16)0.18267 (18)0.0389 (3)
C140.07001 (16)0.39431 (16)0.28674 (17)0.0417 (4)
C150.1422 (3)0.16131 (19)0.2825 (2)0.0680 (5)
H15A0.25260.17870.34240.082*
H15B0.10470.10290.35230.082*
C160.1289 (4)0.0874 (2)0.1617 (3)0.0964 (8)
H16A0.18710.00480.21020.145*
H16B0.01860.07560.09940.145*
H16C0.17250.14340.09720.145*
H130.0199 (17)0.5521 (15)0.0914 (18)0.039 (4)*
H70.456 (2)0.1060 (19)0.108 (2)0.057 (5)*
H40.185 (2)0.4065 (19)0.441 (2)0.057 (5)*
H60.412 (2)0.045 (2)0.366 (2)0.069 (5)*
H50.272 (2)0.191 (2)0.531 (2)0.068 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0631 (7)0.0611 (7)0.0469 (7)0.0170 (6)0.0210 (6)0.0094 (6)
O20.0908 (10)0.0602 (8)0.0860 (10)0.0197 (7)0.0394 (8)0.0439 (7)
O30.0363 (5)0.0398 (6)0.0593 (7)0.0040 (4)0.0190 (5)0.0207 (5)
O40.0550 (7)0.0647 (8)0.0475 (7)0.0024 (6)0.0101 (6)0.0152 (6)
O50.0484 (6)0.0449 (6)0.0565 (7)0.0010 (5)0.0211 (5)0.0183 (5)
N10.0358 (6)0.0434 (7)0.0435 (7)0.0071 (5)0.0146 (5)0.0183 (5)
N20.0396 (7)0.0426 (7)0.0530 (8)0.0098 (5)0.0180 (6)0.0188 (6)
C10.0321 (7)0.0443 (8)0.0442 (8)0.0050 (6)0.0156 (6)0.0131 (7)
C20.0323 (7)0.0377 (7)0.0444 (8)0.0040 (6)0.0150 (6)0.0161 (6)
C30.0303 (7)0.0399 (8)0.0437 (8)0.0018 (6)0.0158 (6)0.0130 (6)
C40.0456 (8)0.0552 (10)0.0481 (9)0.0039 (7)0.0215 (7)0.0162 (8)
C50.0611 (10)0.0609 (11)0.0528 (11)0.0007 (8)0.0302 (9)0.0036 (8)
C60.0592 (10)0.0450 (9)0.0718 (12)0.0044 (8)0.0341 (9)0.0010 (9)
C70.0488 (9)0.0385 (8)0.0658 (11)0.0082 (7)0.0244 (8)0.0157 (8)
C80.0323 (7)0.0383 (7)0.0462 (8)0.0010 (6)0.0155 (6)0.0127 (6)
C90.0392 (8)0.0622 (11)0.0586 (10)0.0101 (7)0.0201 (7)0.0340 (8)
C100.0656 (11)0.0940 (15)0.0544 (11)0.0210 (10)0.0256 (9)0.0397 (10)
C110.0437 (8)0.0378 (8)0.0468 (8)0.0084 (6)0.0193 (7)0.0144 (6)
C120.0640 (11)0.0431 (9)0.0750 (12)0.0091 (8)0.0310 (9)0.0255 (8)
C130.0337 (7)0.0437 (8)0.0429 (8)0.0079 (6)0.0178 (6)0.0165 (6)
C140.0330 (7)0.0488 (9)0.0476 (9)0.0083 (6)0.0191 (7)0.0175 (7)
C150.0826 (13)0.0459 (10)0.0746 (13)0.0091 (9)0.0361 (11)0.0081 (9)
C160.155 (2)0.0543 (12)0.1016 (18)0.0128 (13)0.0756 (18)0.0167 (12)
Geometric parameters (Å, º) top
O1—C11.2004 (18)C6—C71.385 (3)
O2—C91.205 (2)C6—H60.96 (2)
O3—C111.3800 (17)C7—C81.379 (2)
O3—C21.4411 (16)C7—H70.929 (18)
O4—C141.1902 (18)C9—C101.481 (3)
O5—C141.3333 (17)C10—H10A0.9600
O5—C151.450 (2)C10—H10B0.9600
N1—C11.3977 (19)C10—H10C0.9600
N1—C91.4198 (19)C11—C121.481 (2)
N1—C81.435 (2)C12—H12A0.9600
N2—C111.2617 (19)C12—H12B0.9600
N2—C131.4543 (18)C12—H12C0.9600
C1—C21.532 (2)C13—C141.506 (2)
C2—C31.492 (2)C13—H130.955 (16)
C2—C131.5758 (19)C15—C161.478 (3)
C3—C41.378 (2)C15—H15A0.9700
C3—C81.3867 (19)C15—H15B0.9700
C4—C51.386 (2)C16—H16A0.9600
C4—H40.953 (18)C16—H16B0.9600
C5—C61.379 (3)C16—H16C0.9600
C5—H50.94 (2)
C11—O3—C2106.69 (10)C9—C10—H10A109.5
C14—O5—C15117.05 (13)C9—C10—H10B109.5
C1—N1—C9125.83 (13)H10A—C10—H10B109.5
C1—N1—C8109.61 (11)C9—C10—H10C109.5
C9—N1—C8124.12 (12)H10A—C10—H10C109.5
C11—N2—C13107.16 (12)H10B—C10—H10C109.5
O1—C1—N1127.55 (14)N2—C11—O3117.73 (13)
O1—C1—C2124.89 (13)N2—C11—C12127.94 (14)
N1—C1—C2107.48 (12)O3—C11—C12114.32 (13)
O3—C2—C3112.75 (11)C11—C12—H12A109.5
O3—C2—C1111.11 (11)C11—C12—H12B109.5
C3—C2—C1103.06 (11)H12A—C12—H12B109.5
O3—C2—C13101.65 (10)C11—C12—H12C109.5
C3—C2—C13118.28 (11)H12A—C12—H12C109.5
C1—C2—C13110.18 (11)H12B—C12—H12C109.5
C4—C3—C8120.77 (14)N2—C13—C14114.11 (12)
C4—C3—C2129.68 (13)N2—C13—C2104.67 (11)
C8—C3—C2109.55 (12)C14—C13—C2112.86 (11)
C3—C4—C5118.29 (16)N2—C13—H13108.4 (9)
C3—C4—H4121.2 (11)C14—C13—H13107.9 (9)
C5—C4—H4120.5 (11)C2—C13—H13108.7 (9)
C6—C5—C4120.44 (17)O4—C14—O5125.38 (14)
C6—C5—H5119.9 (12)O4—C14—C13126.07 (14)
C4—C5—H5119.6 (12)O5—C14—C13108.54 (12)
C5—C6—C7121.78 (16)O5—C15—C16107.48 (17)
C5—C6—H6119.5 (12)O5—C15—H15A110.2
C7—C6—H6118.7 (12)C16—C15—H15A110.2
C8—C7—C6117.28 (16)O5—C15—H15B110.2
C8—C7—H7121.9 (11)C16—C15—H15B110.2
C6—C7—H7120.8 (11)H15A—C15—H15B108.5
C7—C8—C3121.43 (14)C15—C16—H16A109.5
C7—C8—N1129.06 (13)C15—C16—H16B109.5
C3—C8—N1109.40 (12)H16A—C16—H16B109.5
O2—C9—N1118.75 (16)C15—C16—H16C109.5
O2—C9—C10123.53 (15)H16A—C16—H16C109.5
N1—C9—C10117.71 (15)H16B—C16—H16C109.5
C9—N1—C1—O113.1 (2)C2—C3—C8—N11.85 (15)
C8—N1—C1—O1174.26 (14)C1—N1—C8—C7171.51 (14)
C9—N1—C1—C2163.83 (13)C9—N1—C8—C715.7 (2)
C8—N1—C1—C28.83 (14)C1—N1—C8—C34.57 (15)
C11—O3—C2—C3115.37 (12)C9—N1—C8—C3168.24 (12)
C11—O3—C2—C1129.50 (12)C1—N1—C9—O2163.79 (15)
C11—O3—C2—C1312.29 (14)C8—N1—C9—O27.9 (2)
O1—C1—C2—O352.54 (18)C1—N1—C9—C1016.8 (2)
N1—C1—C2—O3130.45 (12)C8—N1—C9—C10171.52 (13)
O1—C1—C2—C3173.55 (14)C13—N2—C11—O33.51 (18)
N1—C1—C2—C39.44 (14)C13—N2—C11—C12175.54 (16)
O1—C1—C2—C1359.34 (18)C2—O3—C11—N26.54 (18)
N1—C1—C2—C13117.67 (12)C2—O3—C11—C12174.28 (13)
O3—C2—C3—C452.42 (19)C11—N2—C13—C14134.95 (13)
C1—C2—C3—C4172.31 (14)C11—N2—C13—C211.10 (16)
C13—C2—C3—C465.89 (19)O3—C2—C13—N214.18 (14)
O3—C2—C3—C8126.70 (12)C3—C2—C13—N2109.82 (13)
C1—C2—C3—C86.82 (14)C1—C2—C13—N2132.07 (12)
C13—C2—C3—C8114.98 (13)O3—C2—C13—C14138.84 (12)
C8—C3—C4—C50.1 (2)C3—C2—C13—C1414.83 (17)
C2—C3—C4—C5178.98 (14)C1—C2—C13—C14103.28 (14)
C3—C4—C5—C60.7 (2)C15—O5—C14—O42.8 (2)
C4—C5—C6—C70.7 (3)C15—O5—C14—C13177.12 (13)
C5—C6—C7—C80.2 (3)N2—C13—C14—O47.6 (2)
C6—C7—C8—C31.0 (2)C2—C13—C14—O4111.69 (16)
C6—C7—C8—N1176.63 (14)N2—C13—C14—O5172.28 (11)
C4—C3—C8—C70.9 (2)C2—C13—C14—O568.39 (15)
C2—C3—C8—C7178.29 (13)C14—O5—C15—C16163.96 (16)
C4—C3—C8—N1177.36 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O20.93 (2)2.37 (2)2.864 (2)113 (2)
 

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