Ethyl 1-acetyl-2′-methyl-2-oxo-4′,5′-di­hydro-1H-indoline-3-spiro-5′-oxazole-4′-carboxyl­ate

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.

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

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Computing details

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

Crystal data

C16H16N2O5	Z = 2
Mr = 316.31	F(000) = 332
Triclinic, P1	Dx = 1.357 Mg m^−3
a = 9.348 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.614 (2) Å	Cell parameters from 3060 reflections
c = 9.872 (2) Å	θ = 2.4–28.3°
α = 77.015 (4)°	µ = 0.10 mm^−1
β = 63.933 (3)°	T = 293 K
γ = 88.200 (4)°	Block, colourless
V = 774.4 (3) Å^3	0.80 × 0.30 × 0.20 mm

Data collection

Siemens SMART CCD area-detector diffractometer	2665 independent reflections
Radiation source: fine-focus sealed tube	2290 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
Detector resolution: 8.33 pixels mm^-1	θmax = 25.0°, θmin = 2.4°
ω scans	h = −11→11
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	k = −10→11
Tmin = 0.923, Tmax = 0.980	l = −11→11
3825 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0528P)^2 + 0.1374P] where P = (Fo^2 + 2Fc^2)/3
2665 reflections	(Δ/σ)max < 0.001
231 parameters	Δρmax = 0.15 e Å^−3
0 restraints	Δρmin = −0.16 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.30739 (14)	0.57549 (13)	−0.14506 (13)	0.0592 (3)
O2	0.42104 (17)	0.15219 (14)	−0.12144 (17)	0.0745 (4)
O3	0.27378 (11)	0.63940 (10)	0.14496 (12)	0.0444 (3)
O4	−0.16134 (14)	0.37897 (13)	0.42009 (13)	0.0600 (3)
O5	−0.04497 (13)	0.29579 (11)	0.20439 (13)	0.0495 (3)
N1	0.35867 (13)	0.35248 (13)	−0.02983 (14)	0.0407 (3)
N2	0.00556 (14)	0.64982 (13)	0.25250 (15)	0.0449 (3)
C1	0.30131 (16)	0.48861 (16)	−0.03393 (17)	0.0403 (3)
C2	0.21875 (16)	0.50624 (15)	0.13327 (16)	0.0378 (3)
C3	0.26257 (15)	0.37856 (15)	0.22084 (16)	0.0376 (3)
C4	0.23698 (19)	0.34449 (18)	0.37334 (19)	0.0486 (4)
C5	0.2924 (2)	0.2187 (2)	0.4264 (2)	0.0580 (4)
C6	0.3726 (2)	0.13138 (19)	0.3278 (2)	0.0594 (5)
C7	0.3992 (2)	0.16460 (17)	0.1742 (2)	0.0509 (4)
C8	0.34167 (16)	0.28908 (15)	0.12318 (17)	0.0391 (3)
C9	0.40784 (18)	0.27915 (19)	−0.15106 (19)	0.0506 (4)
C10	0.4419 (2)	0.3643 (2)	−0.3084 (2)	0.0682 (5)
H10A	0.4946	0.3077	−0.3827	0.102*
H10B	0.5096	0.4484	−0.3332	0.102*
H10C	0.3435	0.3919	−0.3113	0.102*
C11	0.13932 (17)	0.70613 (15)	0.22284 (17)	0.0424 (3)
C12	0.1726 (2)	0.83908 (18)	0.2595 (2)	0.0587 (5)
H12A	0.0736	0.8737	0.3226	0.088*
H12B	0.2292	0.9103	0.1650	0.088*
H12C	0.2363	0.8194	0.3148	0.088*
C13	0.03618 (16)	0.52730 (16)	0.18267 (18)	0.0389 (3)
C14	−0.07001 (16)	0.39431 (16)	0.28674 (17)	0.0417 (4)
C15	−0.1422 (3)	0.16131 (19)	0.2825 (2)	0.0680 (5)
H15A	−0.2526	0.1787	0.3424	0.082*
H15B	−0.1047	0.1029	0.3523	0.082*
C16	−0.1289 (4)	0.0874 (2)	0.1617 (3)	0.0964 (8)
H16A	−0.1871	−0.0048	0.2102	0.145*
H16B	−0.0186	0.0756	0.0994	0.145*
H16C	−0.1725	0.1434	0.0972	0.145*
H13	0.0199 (17)	0.5521 (15)	0.0914 (18)	0.039 (4)*
H7	0.456 (2)	0.1060 (19)	0.108 (2)	0.057 (5)*
H4	0.185 (2)	0.4065 (19)	0.441 (2)	0.057 (5)*
H6	0.412 (2)	0.045 (2)	0.366 (2)	0.069 (5)*
H5	0.272 (2)	0.191 (2)	0.531 (2)	0.068 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0631 (7)	0.0611 (7)	0.0469 (7)	0.0170 (6)	−0.0210 (6)	−0.0094 (6)
O2	0.0908 (10)	0.0602 (8)	0.0860 (10)	0.0197 (7)	−0.0394 (8)	−0.0439 (7)
O3	0.0363 (5)	0.0398 (6)	0.0593 (7)	0.0040 (4)	−0.0190 (5)	−0.0207 (5)
O4	0.0550 (7)	0.0647 (8)	0.0475 (7)	−0.0024 (6)	−0.0101 (6)	−0.0152 (6)
O5	0.0484 (6)	0.0449 (6)	0.0565 (7)	0.0010 (5)	−0.0211 (5)	−0.0183 (5)
N1	0.0358 (6)	0.0434 (7)	0.0435 (7)	0.0071 (5)	−0.0146 (5)	−0.0183 (5)
N2	0.0396 (7)	0.0426 (7)	0.0530 (8)	0.0098 (5)	−0.0180 (6)	−0.0188 (6)
C1	0.0321 (7)	0.0443 (8)	0.0442 (8)	0.0050 (6)	−0.0156 (6)	−0.0131 (7)
C2	0.0323 (7)	0.0377 (7)	0.0444 (8)	0.0040 (6)	−0.0150 (6)	−0.0161 (6)
C3	0.0303 (7)	0.0399 (8)	0.0437 (8)	0.0018 (6)	−0.0158 (6)	−0.0130 (6)
C4	0.0456 (8)	0.0552 (10)	0.0481 (9)	0.0039 (7)	−0.0215 (7)	−0.0162 (8)
C5	0.0611 (10)	0.0609 (11)	0.0528 (11)	−0.0007 (8)	−0.0302 (9)	−0.0036 (8)
C6	0.0592 (10)	0.0450 (9)	0.0718 (12)	0.0044 (8)	−0.0341 (9)	0.0010 (9)
C7	0.0488 (9)	0.0385 (8)	0.0658 (11)	0.0082 (7)	−0.0244 (8)	−0.0157 (8)
C8	0.0323 (7)	0.0383 (7)	0.0462 (8)	0.0010 (6)	−0.0155 (6)	−0.0127 (6)
C9	0.0392 (8)	0.0622 (11)	0.0586 (10)	0.0101 (7)	−0.0201 (7)	−0.0340 (8)
C10	0.0656 (11)	0.0940 (15)	0.0544 (11)	0.0210 (10)	−0.0256 (9)	−0.0397 (10)
C11	0.0437 (8)	0.0378 (8)	0.0468 (8)	0.0084 (6)	−0.0193 (7)	−0.0144 (6)
C12	0.0640 (11)	0.0431 (9)	0.0750 (12)	0.0091 (8)	−0.0310 (9)	−0.0255 (8)
C13	0.0337 (7)	0.0437 (8)	0.0429 (8)	0.0079 (6)	−0.0178 (6)	−0.0165 (6)
C14	0.0330 (7)	0.0488 (9)	0.0476 (9)	0.0083 (6)	−0.0191 (7)	−0.0175 (7)
C15	0.0826 (13)	0.0459 (10)	0.0746 (13)	−0.0091 (9)	−0.0361 (11)	−0.0081 (9)
C16	0.155 (2)	0.0543 (12)	0.1016 (18)	−0.0128 (13)	−0.0756 (18)	−0.0167 (12)

Geometric parameters (Å, º)

O1—C1	1.2004 (18)	C6—C7	1.385 (3)
O2—C9	1.205 (2)	C6—H6	0.96 (2)
O3—C11	1.3800 (17)	C7—C8	1.379 (2)
O3—C2	1.4411 (16)	C7—H7	0.929 (18)
O4—C14	1.1902 (18)	C9—C10	1.481 (3)
O5—C14	1.3333 (17)	C10—H10A	0.9600
O5—C15	1.450 (2)	C10—H10B	0.9600
N1—C1	1.3977 (19)	C10—H10C	0.9600
N1—C9	1.4198 (19)	C11—C12	1.481 (2)
N1—C8	1.435 (2)	C12—H12A	0.9600
N2—C11	1.2617 (19)	C12—H12B	0.9600
N2—C13	1.4543 (18)	C12—H12C	0.9600
C1—C2	1.532 (2)	C13—C14	1.506 (2)
C2—C3	1.492 (2)	C13—H13	0.955 (16)
C2—C13	1.5758 (19)	C15—C16	1.478 (3)
C3—C4	1.378 (2)	C15—H15A	0.9700
C3—C8	1.3867 (19)	C15—H15B	0.9700
C4—C5	1.386 (2)	C16—H16A	0.9600
C4—H4	0.953 (18)	C16—H16B	0.9600
C5—C6	1.379 (3)	C16—H16C	0.9600
C5—H5	0.94 (2)
C11—O3—C2	106.69 (10)	C9—C10—H10A	109.5
C14—O5—C15	117.05 (13)	C9—C10—H10B	109.5
C1—N1—C9	125.83 (13)	H10A—C10—H10B	109.5
C1—N1—C8	109.61 (11)	C9—C10—H10C	109.5
C9—N1—C8	124.12 (12)	H10A—C10—H10C	109.5
C11—N2—C13	107.16 (12)	H10B—C10—H10C	109.5
O1—C1—N1	127.55 (14)	N2—C11—O3	117.73 (13)
O1—C1—C2	124.89 (13)	N2—C11—C12	127.94 (14)
N1—C1—C2	107.48 (12)	O3—C11—C12	114.32 (13)
O3—C2—C3	112.75 (11)	C11—C12—H12A	109.5
O3—C2—C1	111.11 (11)	C11—C12—H12B	109.5
C3—C2—C1	103.06 (11)	H12A—C12—H12B	109.5
O3—C2—C13	101.65 (10)	C11—C12—H12C	109.5
C3—C2—C13	118.28 (11)	H12A—C12—H12C	109.5
C1—C2—C13	110.18 (11)	H12B—C12—H12C	109.5
C4—C3—C8	120.77 (14)	N2—C13—C14	114.11 (12)
C4—C3—C2	129.68 (13)	N2—C13—C2	104.67 (11)
C8—C3—C2	109.55 (12)	C14—C13—C2	112.86 (11)
C3—C4—C5	118.29 (16)	N2—C13—H13	108.4 (9)
C3—C4—H4	121.2 (11)	C14—C13—H13	107.9 (9)
C5—C4—H4	120.5 (11)	C2—C13—H13	108.7 (9)
C6—C5—C4	120.44 (17)	O4—C14—O5	125.38 (14)
C6—C5—H5	119.9 (12)	O4—C14—C13	126.07 (14)
C4—C5—H5	119.6 (12)	O5—C14—C13	108.54 (12)
C5—C6—C7	121.78 (16)	O5—C15—C16	107.48 (17)
C5—C6—H6	119.5 (12)	O5—C15—H15A	110.2
C7—C6—H6	118.7 (12)	C16—C15—H15A	110.2
C8—C7—C6	117.28 (16)	O5—C15—H15B	110.2
C8—C7—H7	121.9 (11)	C16—C15—H15B	110.2
C6—C7—H7	120.8 (11)	H15A—C15—H15B	108.5
C7—C8—C3	121.43 (14)	C15—C16—H16A	109.5
C7—C8—N1	129.06 (13)	C15—C16—H16B	109.5
C3—C8—N1	109.40 (12)	H16A—C16—H16B	109.5
O2—C9—N1	118.75 (16)	C15—C16—H16C	109.5
O2—C9—C10	123.53 (15)	H16A—C16—H16C	109.5
N1—C9—C10	117.71 (15)	H16B—C16—H16C	109.5
C9—N1—C1—O1	−13.1 (2)	C2—C3—C8—N1	1.85 (15)
C8—N1—C1—O1	174.26 (14)	C1—N1—C8—C7	−171.51 (14)
C9—N1—C1—C2	163.83 (13)	C9—N1—C8—C7	15.7 (2)
C8—N1—C1—C2	−8.83 (14)	C1—N1—C8—C3	4.57 (15)
C11—O3—C2—C3	−115.37 (12)	C9—N1—C8—C3	−168.24 (12)
C11—O3—C2—C1	129.50 (12)	C1—N1—C9—O2	−163.79 (15)
C11—O3—C2—C13	12.29 (14)	C8—N1—C9—O2	7.9 (2)
O1—C1—C2—O3	−52.54 (18)	C1—N1—C9—C10	16.8 (2)
N1—C1—C2—O3	130.45 (12)	C8—N1—C9—C10	−171.52 (13)
O1—C1—C2—C3	−173.55 (14)	C13—N2—C11—O3	−3.51 (18)
N1—C1—C2—C3	9.44 (14)	C13—N2—C11—C12	175.54 (16)
O1—C1—C2—C13	59.34 (18)	C2—O3—C11—N2	−6.54 (18)
N1—C1—C2—C13	−117.67 (12)	C2—O3—C11—C12	174.28 (13)
O3—C2—C3—C4	52.42 (19)	C11—N2—C13—C14	134.95 (13)
C1—C2—C3—C4	172.31 (14)	C11—N2—C13—C2	11.10 (16)
C13—C2—C3—C4	−65.89 (19)	O3—C2—C13—N2	−14.18 (14)
O3—C2—C3—C8	−126.70 (12)	C3—C2—C13—N2	109.82 (13)
C1—C2—C3—C8	−6.82 (14)	C1—C2—C13—N2	−132.07 (12)
C13—C2—C3—C8	114.98 (13)	O3—C2—C13—C14	−138.84 (12)
C8—C3—C4—C5	0.1 (2)	C3—C2—C13—C14	−14.83 (17)
C2—C3—C4—C5	−178.98 (14)	C1—C2—C13—C14	103.28 (14)
C3—C4—C5—C6	0.7 (2)	C15—O5—C14—O4	2.8 (2)
C4—C5—C6—C7	−0.7 (3)	C15—O5—C14—C13	−177.12 (13)
C5—C6—C7—C8	−0.2 (3)	N2—C13—C14—O4	−7.6 (2)
C6—C7—C8—C3	1.0 (2)	C2—C13—C14—O4	111.69 (16)
C6—C7—C8—N1	176.63 (14)	N2—C13—C14—O5	172.28 (11)
C4—C3—C8—C7	−0.9 (2)	C2—C13—C14—O5	−68.39 (15)
C2—C3—C8—C7	178.29 (13)	C14—O5—C15—C16	163.96 (16)
C4—C3—C8—N1	−177.36 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O2	0.93 (2)	2.37 (2)	2.864 (2)	113 (2)