1-Acetyl-5,6-dimethoxy­indoline at 123 K

Cheng, X.-W.

doi:10.1107/S1600536808017376

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 7| July 2008| Page o1309

doi:10.1107/S1600536808017376

Open

access

1-Acetyl-5,6-dimethoxyindoline at 123 K

Xiang-Wei Cheng ^a ^*

^aZhejiang Police College Experience Center, Zhejiang Police College, Hangzhou 310053, People's Republic of China
^*Correspondence e-mail: zpccxw@126.com

(Received 4 April 2008; accepted 9 June 2008; online 19 June 2008)

In the title compound, C₁₂H₁₅NO₃, all C, N and O atoms lie in a mirror plane. An intramolecular C—H⋯O hydrogen bond is present.

Related literature

For the synthesis, see: Kuwano et al. (2006 ). For general background, see: Fernandez et al. (2006 ); Amit et al. (1976 ). For a related structure, see: Moreno et al. (1998 ).

Experimental

Crystal data

C₁₂H₁₅NO₃
M_r = 221.25
Orthorhombic, P n m a
a = 18.541 (4) Å
b = 6.9572 (15) Å
c = 8.5582 (17) Å
V = 1103.9 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 123 (2) K
0.29 × 0.26 × 0.25 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.963, T_max = 0.976
11013 measured reflections
1054 independent reflections
964 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.148
S = 1.40
1054 reflections
97 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.59 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O3	0.95	2.30	2.861 (2)	117

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808017376/wk2084sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808017376/wk2084Isup2.hkl

checkCIF report

Comment top

The indoline cores have attracted particular attention in recent years due to their presence in a great variety of natural products, biologically active alkaloids and pharmaceuticals (Fernandez et al., 2006). Some nitro derivative compounds of 1-acetyl-indoline can undergo photosolvolysis which points to some possible use in the synthesis of peptides (Amit et al., 1976). Here the crystal structure of the title compound is reported.

The title molecule (Fig.1), displays mirror symmetry , with all C, N atom and O atoms lying in the mirror plane.

Related literature top

For the synthesis, see: Kuwano et al. (2006). For general background, see: Fernandez et al. (2006); Amit et al. (1976). For a related structure, see: Moreno et al. (1998).

Experimental top

The title compound was prepared according to the literature method (Kuwano et al., 2006). Crystals suitable for X-ray analysis were obtained by slow evaporation of an isopropanol solution at 295 K.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atomic numbering.

1-Acetyl-5,6-dimethoxyindoline top

Crystal data top

C₁₂H₁₅NO₃	F(000) = 472
M_r = 221.25	D_x = 1.331 Mg m⁻³
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 1054 reflections
a = 18.541 (4) Å	θ = 2.2–25.0°
b = 6.9572 (15) Å	µ = 0.10 mm⁻¹
c = 8.5582 (17) Å	T = 123 K
V = 1103.9 (4) Å³	Block, colourless
Z = 4	0.29 × 0.26 × 0.25 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1054 independent reflections
Radiation source: fine-focus sealed tube	964 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −20→22
T_min = 0.963, T_max = 0.976	k = −8→7
11013 measured reflections	l = −10→10

Refinement top

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.148	H-atom parameters constrained
S = 1.40	w = 1/[σ²(F_o²) + (0.0677P)² + 0.2P] where P = (F_o² + 2F_c²)/3
1054 reflections	(Δ/σ)_max < 0.001
97 parameters	Δρ_max = 0.41 e Å⁻³
6 restraints	Δρ_min = −0.59 e Å⁻³

Crystal data top

C₁₂H₁₅NO₃	V = 1103.9 (4) Å³
M_r = 221.25	Z = 4
Orthorhombic, Pnma	Mo Kα radiation
a = 18.541 (4) Å	µ = 0.10 mm⁻¹
b = 6.9572 (15) Å	T = 123 K
c = 8.5582 (17) Å	0.29 × 0.26 × 0.25 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1054 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	964 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.976	R_int = 0.028
11013 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	6 restraints
wR(F²) = 0.148	H-atom parameters constrained
S = 1.40	Δρ_max = 0.41 e Å⁻³
1054 reflections	Δρ_min = −0.59 e Å⁻³
97 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O2	0.74869 (9)	0.2500	0.6594 (2)	0.0501 (6)
O1	0.78145 (11)	0.2500	0.9506 (2)	0.0526 (6)
O3	0.95611 (11)	0.2500	0.2934 (2)	0.0602 (7)
N1	1.00964 (12)	0.2500	0.5307 (3)	0.0412 (6)
C3	0.96484 (14)	0.2500	0.7812 (3)	0.0399 (7)
C4	0.94640 (14)	0.2500	0.6247 (3)	0.0366 (6)
C6	0.82118 (14)	0.2500	0.6909 (3)	0.0369 (6)
C11	1.01159 (15)	0.2500	0.3721 (3)	0.0439 (7)
C5	0.87457 (14)	0.2500	0.5772 (3)	0.0375 (6)
H5	0.8626	0.2500	0.4717	0.045*
C1	0.83923 (14)	0.2500	0.8506 (3)	0.0397 (7)
C2	0.91147 (14)	0.2500	0.8952 (3)	0.0424 (7)
H2	0.9239	0.2500	1.0005	0.051*
C12	1.08471 (16)	0.2500	0.2962 (4)	0.0529 (8)
H12A	1.1214	0.2500	0.3754	0.079*
H12B	1.0897	0.3627	0.2324	0.079*	0.50
H12C	1.0897	0.1373	0.2324	0.079*	0.50
C9	1.04564 (15)	0.2500	0.8003 (4)	0.0515 (8)
H9A	1.0616	0.1365	0.8563	0.062*	0.50
H9B	1.0616	0.3635	0.8563	0.062*	0.50
C8	0.72852 (17)	0.2500	0.4986 (3)	0.0595 (9)
H8A	0.6769	0.2500	0.4902	0.089*
H8B	0.7475	0.1373	0.4487	0.089*	0.50
H8C	0.7475	0.3627	0.4487	0.089*	0.50
C10	1.07441 (15)	0.2500	0.6328 (4)	0.0533 (8)
H10A	1.1036	0.3633	0.6137	0.064*	0.50
H10B	1.1036	0.1367	0.6137	0.064*	0.50
C7	0.79744 (19)	0.2500	1.1138 (3)	0.0658 (10)
H7A	0.7533	0.2500	1.1723	0.099*
H7B	0.8249	0.3627	1.1394	0.099*	0.50
H7C	0.8249	0.1373	1.1394	0.099*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.0326 (11)	0.0844 (15)	0.0334 (10)	0.000	−0.0007 (7)	0.000
O1	0.0446 (12)	0.0827 (15)	0.0304 (10)	0.000	0.0041 (8)	0.000
O3	0.0465 (13)	0.0931 (18)	0.0410 (12)	0.000	0.0042 (9)	0.000
N1	0.0325 (12)	0.0470 (14)	0.0440 (13)	0.000	0.0020 (9)	0.000
C3	0.0377 (15)	0.0415 (14)	0.0406 (15)	0.000	−0.0061 (11)	0.000
C4	0.0342 (14)	0.0362 (13)	0.0395 (14)	0.000	0.0002 (11)	0.000
C6	0.0317 (13)	0.0443 (14)	0.0348 (13)	0.000	−0.0014 (10)	0.000
C11	0.0416 (16)	0.0437 (15)	0.0463 (14)	0.000	0.0065 (13)	0.000
C5	0.0372 (14)	0.0436 (14)	0.0317 (12)	0.000	−0.0019 (11)	0.000
C1	0.0397 (15)	0.0449 (15)	0.0345 (13)	0.000	0.0013 (11)	0.000
C2	0.0474 (16)	0.0484 (16)	0.0313 (13)	0.000	−0.0074 (11)	0.000
C12	0.0473 (18)	0.0518 (17)	0.0595 (18)	0.000	0.0154 (14)	0.000
C9	0.0392 (17)	0.0622 (19)	0.0532 (18)	0.000	−0.0133 (13)	0.000
C8	0.0360 (16)	0.105 (3)	0.0374 (15)	0.000	−0.0043 (12)	0.000
C10	0.0319 (15)	0.0640 (19)	0.0639 (19)	0.000	−0.0025 (13)	0.000
C7	0.061 (2)	0.105 (3)	0.0311 (14)	0.000	0.0030 (14)	0.000

Geometric parameters (Å, º) top

O2—C6	1.371 (3)	C1—C2	1.393 (4)
O2—C8	1.426 (3)	C2—H2	0.9300
O1—C1	1.371 (3)	C12—H12A	0.9600
O1—C7	1.428 (3)	C12—H12B	0.9600
O3—C11	1.230 (3)	C12—H12C	0.9600
N1—C11	1.358 (4)	C9—C10	1.530 (5)
N1—C4	1.422 (3)	C9—H9A	0.9700
N1—C10	1.485 (4)	C9—H9B	0.9700
C3—C4	1.383 (4)	C8—H8A	0.9600
C3—C2	1.389 (4)	C8—H8B	0.9600
C3—C9	1.507 (4)	C8—H8C	0.9600
C4—C5	1.392 (4)	C10—H10A	0.9700
C6—C5	1.388 (4)	C10—H10B	0.9700
C6—C1	1.408 (4)	C7—H7A	0.9600
C11—C12	1.503 (4)	C7—H7B	0.9600
C5—H5	0.9300	C7—H7C	0.9600

C6—O2—C8	116.6 (2)	H12A—C12—H12B	109.5
C1—O1—C7	116.6 (2)	C11—C12—H12C	109.5
C11—N1—C4	126.0 (2)	H12A—C12—H12C	109.5
C11—N1—C10	124.5 (2)	H12B—C12—H12C	109.5
C4—N1—C10	109.5 (2)	C3—C9—C10	104.2 (2)
C4—C3—C2	120.3 (2)	C3—C9—H9A	110.9
C4—C3—C9	110.5 (2)	C10—C9—H9A	110.9
C2—C3—C9	129.2 (2)	C3—C9—H9B	110.9
C3—C4—C5	121.3 (2)	C10—C9—H9B	110.9
C3—C4—N1	110.1 (2)	H9A—C9—H9B	108.9
C5—C4—N1	128.6 (2)	O2—C8—H8A	109.5
O2—C6—C5	124.2 (2)	O2—C8—H8B	109.5
O2—C6—C1	115.1 (2)	H8A—C8—H8B	109.5
C5—C6—C1	120.7 (2)	O2—C8—H8C	109.5
O3—C11—N1	121.7 (2)	H8A—C8—H8C	109.5
O3—C11—C12	121.2 (3)	H8B—C8—H8C	109.5
N1—C11—C12	117.1 (3)	N1—C10—C9	105.6 (2)
C6—C5—C4	118.5 (2)	N1—C10—H10A	110.6
C6—C5—H5	120.7	C9—C10—H10A	110.6
C4—C5—H5	120.7	N1—C10—H10B	110.6
O1—C1—C2	125.5 (2)	C9—C10—H10B	110.6
O1—C1—C6	114.8 (2)	H10A—C10—H10B	108.7
C2—C1—C6	119.6 (2)	O1—C7—H7A	109.5
C3—C2—C1	119.5 (2)	O1—C7—H7B	109.5
C3—C2—H2	120.2	H7A—C7—H7B	109.5
C1—C2—H2	120.2	O1—C7—H7C	109.5
C11—C12—H12A	109.5	H7A—C7—H7C	109.5
C11—C12—H12B	109.5	H7B—C7—H7C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O3	0.95	2.30	2.861 (2)	117

Experimental details

Crystal data
Chemical formula	C₁₂H₁₅NO₃
M_r	221.25
Crystal system, space group	Orthorhombic, Pnma
Temperature (K)	123
a, b, c (Å)	18.541 (4), 6.9572 (15), 8.5582 (17)
V (Å³)	1103.9 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.29 × 0.26 × 0.25

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.963, 0.976
No. of measured, independent and observed [I > 2σ(I)] reflections	11013, 1054, 964
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.148, 1.40
No. of reflections	1054
No. of parameters	97
No. of restraints	6
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.59

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O3	0.95	2.30	2.861 (2)	117

Acknowledgements

The author acknowledges financial support from Zhejiang Police College, China.

References

Amit, B., Ben-Efraim, D. A. & Patchornik, A. (1976). J. Am. Chem. Soc. 98, 834–835. CrossRef Web of Science Google Scholar
Bruker (2002). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fernandez, V. G., Fernandez-Torres, P. & Gotor, V. (2006). Tetrahedron Asymmetry, 17, 2558–2564. Google Scholar
Kuwano, R., Kashiwabara, M., Sato, K., Ito, T., Kaneda, K. & Ito, Y. (2006). Tetrahedron Asymmetry, 17, 521–535. Web of Science CrossRef CAS Google Scholar
Moreno, M. M. T., Santos, R. H. A., Gambardella, M. T. P., Camargo, A. J., Da Silva, A. B. F. & Trsic, M. (1998). Struct. Chem. 9, 365–373. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar