Ethyl 2-(2,3-dioxoindolin-1-yl)acetate

The mol­ecular structure of the title compound, C₁₂H₁₁NO₄, at 100 (2) K is characterized by a planar indole ring system, containing a long C-C bond in the 1,2-diketone unit.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.040
• wR factor = 0.104
• Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT432_ALERT_2_B Short Inter X...Y Contact  O2     ..  C3      ..       2.87 Ang.

Alert level C
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C1     -   C3     ...       1.56 Ang.

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 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
   0 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

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Computing details

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

Ethyl 2-(2,3-dioxoindolin-1-yl)acetate

Crystal data

C12H11NO4	F(000) = 488
Mr = 233.22	Dx = 1.453 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 3255 reflections
a = 13.6433 (6) Å	θ = 3.3–70.3°
b = 4.9505 (3) Å	µ = 0.93 mm^−1
c = 16.2899 (8) Å	T = 100 K
β = 104.246 (2)°	Block, orange
V = 1066.40 (10) Å^3	0.5 × 0.2 × 0.2 mm
Z = 4

Data collection

Bruker SMART 6000 diffractometer	2000 independent reflections
Radiation source: fine-focus sealed tube	1725 reflections with I > 2σ(I)
Crossed Goebel mirrors monochromator	Rint = 0.048
ω and φ scans	θmax = 70.3°, θmin = 3.3°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −16→16
Tmin = 0.594, Tmax = 0.831	k = −5→6
10352 measured reflections	l = −19→19

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.104	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0564P)^2 + 0.3661P] where P = (Fo^2 + 2Fc^2)/3
2000 reflections	(Δ/σ)max < 0.001
155 parameters	Δρmax = 0.33 e Å^−3
0 restraints	Δρmin = −0.21 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
C1	0.60794 (11)	0.8944 (3)	0.78627 (9)	0.0168 (3)
O2	0.58879 (8)	1.0495 (2)	0.72671 (7)	0.0209 (3)
C3	0.56599 (11)	0.9004 (3)	0.86695 (9)	0.0166 (3)
O4	0.50308 (8)	1.0589 (2)	0.87787 (7)	0.0211 (3)
C5	0.62080 (10)	0.6848 (3)	0.92122 (9)	0.0163 (3)
C6	0.61795 (11)	0.6038 (3)	1.00197 (9)	0.0189 (3)
H6	0.5748	0.6910	1.0315	0.023*
C7	0.68022 (12)	0.3908 (3)	1.03865 (9)	0.0209 (3)
H7	0.6797	0.3303	1.0939	0.025*
C8	0.74314 (11)	0.2664 (3)	0.99462 (10)	0.0206 (3)
H8	0.7851	0.1217	1.0208	0.025*
C9	0.74672 (11)	0.3474 (3)	0.91294 (9)	0.0181 (3)
H9	0.7900	0.2609	0.8834	0.022*
C10	0.68436 (10)	0.5588 (3)	0.87729 (9)	0.0155 (3)
N11	0.67385 (9)	0.6806 (2)	0.79704 (7)	0.0165 (3)
C12	0.72442 (11)	0.5980 (3)	0.73313 (9)	0.0172 (3)
H12A	0.6761	0.6084	0.6769	0.021*
H12B	0.7458	0.4073	0.7432	0.021*
C13	0.81627 (11)	0.7699 (3)	0.73224 (9)	0.0176 (3)
O14	0.84687 (8)	0.9564 (2)	0.77891 (7)	0.0266 (3)
O15	0.85739 (8)	0.6869 (2)	0.67021 (7)	0.0198 (3)
C16	0.94114 (11)	0.8490 (3)	0.65638 (10)	0.0231 (4)
H16A	1.0004	0.8333	0.7055	0.028*
H16B	0.9213	1.0415	0.6490	0.028*
C17	0.96670 (12)	0.7429 (4)	0.57764 (11)	0.0276 (4)
H17A	0.9854	0.5518	0.5855	0.041*
H17B	1.0235	0.8458	0.5667	0.041*
H17C	0.9078	0.7620	0.5294	0.041*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0177 (7)	0.0136 (7)	0.0182 (7)	−0.0019 (5)	0.0028 (5)	−0.0020 (5)
O2	0.0255 (6)	0.0177 (5)	0.0185 (6)	−0.0004 (4)	0.0037 (4)	0.0024 (4)
C3	0.0157 (6)	0.0147 (7)	0.0188 (7)	−0.0029 (5)	0.0030 (5)	−0.0034 (5)
O4	0.0188 (5)	0.0200 (5)	0.0243 (6)	0.0028 (4)	0.0047 (4)	−0.0045 (4)
C5	0.0160 (6)	0.0149 (7)	0.0178 (7)	−0.0022 (5)	0.0036 (5)	−0.0021 (5)
C6	0.0206 (7)	0.0199 (7)	0.0171 (8)	−0.0041 (6)	0.0063 (6)	−0.0041 (6)
C7	0.0266 (8)	0.0202 (7)	0.0146 (7)	−0.0050 (6)	0.0027 (6)	0.0001 (5)
C8	0.0213 (7)	0.0164 (7)	0.0204 (8)	−0.0015 (6)	−0.0016 (6)	0.0004 (5)
C9	0.0165 (7)	0.0175 (7)	0.0200 (8)	−0.0008 (5)	0.0038 (5)	−0.0034 (6)
C10	0.0150 (6)	0.0153 (7)	0.0159 (7)	−0.0053 (5)	0.0031 (5)	−0.0028 (5)
N11	0.0185 (6)	0.0165 (6)	0.0155 (6)	0.0004 (5)	0.0059 (5)	−0.0005 (4)
C12	0.0190 (7)	0.0174 (7)	0.0160 (7)	−0.0004 (5)	0.0060 (5)	−0.0022 (5)
C13	0.0177 (7)	0.0179 (7)	0.0171 (7)	0.0029 (6)	0.0039 (5)	0.0005 (5)
O14	0.0239 (6)	0.0272 (6)	0.0306 (7)	−0.0066 (5)	0.0102 (5)	−0.0115 (5)
O15	0.0199 (5)	0.0212 (5)	0.0207 (6)	−0.0028 (4)	0.0095 (4)	−0.0026 (4)
C16	0.0182 (7)	0.0259 (8)	0.0263 (8)	−0.0035 (6)	0.0078 (6)	0.0028 (6)
C17	0.0218 (7)	0.0383 (9)	0.0249 (8)	0.0004 (7)	0.0101 (6)	0.0067 (7)

Geometric parameters (Å, º)

C1—O2	1.2143 (18)	C10—N11	1.4146 (19)
C1—N11	1.3718 (19)	N11—C12	1.4426 (18)
C1—C3	1.558 (2)	C12—C13	1.518 (2)
C3—O4	1.2078 (18)	C12—H12A	0.9900
C3—C5	1.468 (2)	C12—H12B	0.9900
C5—C6	1.385 (2)	C13—O14	1.2036 (18)
C5—C10	1.400 (2)	C13—O15	1.3354 (18)
C6—C7	1.393 (2)	O15—C16	1.4584 (18)
C6—H6	0.9500	C16—C17	1.504 (2)
C7—C8	1.390 (2)	C16—H16A	0.9900
C7—H7	0.9500	C16—H16B	0.9900
C8—C9	1.402 (2)	C17—H17A	0.9800
C8—H8	0.9500	C17—H17B	0.9800
C9—C10	1.383 (2)	C17—H17C	0.9800
C9—H9	0.9500
O2—C1—N11	126.56 (14)	C1—N11—C12	122.77 (12)
O2—C1—C3	127.63 (13)	C10—N11—C12	126.04 (12)
N11—C1—C3	105.79 (12)	N11—C12—C13	112.98 (12)
O4—C3—C5	131.21 (14)	N11—C12—H12A	109.0
O4—C3—C1	123.97 (13)	C13—C12—H12A	109.0
C5—C3—C1	104.82 (11)	N11—C12—H12B	109.0
C6—C5—C10	121.49 (13)	C13—C12—H12B	109.0
C6—C5—C3	130.79 (13)	H12A—C12—H12B	107.8
C10—C5—C3	107.71 (12)	O14—C13—O15	124.66 (14)
C5—C6—C7	118.02 (14)	O14—C13—C12	125.66 (14)
C5—C6—H6	121.0	O15—C13—C12	109.66 (12)
C7—C6—H6	121.0	C13—O15—C16	116.03 (12)
C8—C7—C6	120.17 (14)	O15—C16—C17	107.12 (13)
C8—C7—H7	119.9	O15—C16—H16A	110.3
C6—C7—H7	119.9	C17—C16—H16A	110.3
C7—C8—C9	122.23 (14)	O15—C16—H16B	110.3
C7—C8—H8	118.9	C17—C16—H16B	110.3
C9—C8—H8	118.9	H16A—C16—H16B	108.5
C10—C9—C8	116.95 (14)	C16—C17—H17A	109.5
C10—C9—H9	121.5	C16—C17—H17B	109.5
C8—C9—H9	121.5	H17A—C17—H17B	109.5
C9—C10—C5	121.14 (14)	C16—C17—H17C	109.5
C9—C10—N11	128.51 (13)	H17A—C17—H17C	109.5
C5—C10—N11	110.35 (12)	H17B—C17—H17C	109.5
C1—N11—C10	111.19 (12)