Related literature {#sec1}
==================

For the synthesis, see: Kuwano *et al.* (2006[@bb4]). For general background, see: Fernandez *et al.* (2006[@bb3]); Amit *et al.* (1976[@bb1]). For a related structure, see: Moreno *et al.* (1998[@bb5]).

Experimental {#sec2}
============

 {#sec2.1}

### Crystal data {#sec2.1.1}

C~12~H~15~NO~3~*M* *~r~* = 221.25Orthorhombic,*a* = 18.541 (4) Å*b* = 6.9572 (15) Å*c* = 8.5582 (17) Å*V* = 1103.9 (4) Å^3^*Z* = 4Mo *K*α radiationμ = 0.10 mm^−1^*T* = 123 (2) K0.29 × 0.26 × 0.25 mm

### Data collection {#sec2.1.2}

Bruker SMART CCD area-detector diffractometerAbsorption correction: multi-scan (*SADABS*; Bruker, 2002[@bb2]) *T* ~min~ = 0.963, *T* ~max~ = 0.97611013 measured reflections1054 independent reflections964 reflections with *I* \> 2σ(*I*)*R* ~int~ = 0.028

### Refinement {#sec2.1.3}

*R*\[*F* ^2^ \> 2σ(*F* ^2^)\] = 0.057*wR*(*F* ^2^) = 0.148*S* = 1.401054 reflections97 parameters6 restraintsH-atom parameters constrainedΔρ~max~ = 0.41 e Å^−3^Δρ~min~ = −0.59 e Å^−3^

 {#d5e365}

Data collection: *SMART* (Bruker, 2002[@bb2]); cell refinement: *SAINT* (Bruker, 2002[@bb2]); data reduction: *SAINT*; program(s) used to solve structure: *SHELXS97* (Sheldrick, 2008[@bb6]); program(s) used to refine structure: *SHELXL97* (Sheldrick, 2008[@bb6]); molecular graphics: *SHELXTL* (Sheldrick, 2008[@bb6]); software used to prepare material for publication: *SHELXTL*.

Supplementary Material
======================

Crystal structure: contains datablocks global, I. DOI: [10.1107/S1600536808017376/wk2084sup1.cif](http://dx.doi.org/10.1107/S1600536808017376/wk2084sup1.cif)

Structure factors: contains datablocks I. DOI: [10.1107/S1600536808017376/wk2084Isup2.hkl](http://dx.doi.org/10.1107/S1600536808017376/wk2084Isup2.hkl)

Additional supplementary materials: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?wk2084&file=wk2084sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?wk2084sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?wk2084&checkcif=yes)

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: [WK2084](http://scripts.iucr.org/cgi-bin/sendsup?wk2084)).

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

Comment
=======

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.

Experimental {#experimental}
============

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.

Refinement {#refinement}
==========

H atoms were positioned geometrically (C-H = 0.95-0.99 Å) and refined using a riding model, with *U*~iso~(H) = 1.2--1.5*U*~eq~(C).

Figures
=======

![Molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atomic numbering.](e-64-o1309-fig1){#Fap1}

Crystal data {#tablewrapcrystaldatalong}
============

  ------------------------ ---------------------------------------
  C~12~H~15~NO~3~          *F*~000~ = 472
  *M~r~* = 221.25          *D*~x~ = 1.331 Mg m^−3^
  Orthorhombic, *Pnma*     Mo *K*α radiation λ = 0.71073 Å
  Hall symbol: -P 2ac 2n   Cell parameters from 1054 reflections
  *a* = 18.541 (4) Å       θ = 2.2--25.0º
  *b* = 6.9572 (15) Å      µ = 0.10 mm^−1^
  *c* = 8.5582 (17) Å      *T* = 123 (2) K
  *V* = 1103.9 (4) Å^3^    Block, colourless
  *Z* = 4                  0.29 × 0.26 × 0.25 mm
  ------------------------ ---------------------------------------

Data collection {#tablewrapdatacollectionlong}
===============

  --------------------------------------------------------- -------------------------------------
  Bruker SMART CCD area-detector diffractometer             1054 independent reflections
  Radiation source: fine-focus sealed tube                  964 reflections with *I* \> 2σ(*I*)
  Monochromator: graphite                                   *R*~int~ = 0.028
  *T* = 123(2) K                                            θ~max~ = 25.0º
  ω scans                                                   θ~min~ = 2.2º
  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 {#tablewraprefinementdatalong}
==========

  ---------------------------------------------------------------- ------------------------------------------------------------------------------------------------
  Refinement on *F*^2^                                             Secondary atom site location: difference Fourier map
  Least-squares matrix: full                                       Hydrogen site location: inferred from neighbouring sites
  *R*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.057                              H-atom parameters constrained
  *wR*(*F*^2^) = 0.148                                               *w* = 1/\[σ^2^(*F*~o~^2^) + (0.0677*P*)^2^ + 0.2*P*\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  *S* = 1.40                                                       (Δ/σ)~max~ \< 0.001
  1054 reflections                                                 Δρ~max~ = 0.41 e Å^−3^
  97 parameters                                                    Δρ~min~ = −0.59 e Å^−3^
  6 restraints                                                     Extinction correction: none
  Primary atom site location: structure-invariant direct methods   
  ---------------------------------------------------------------- ------------------------------------------------------------------------------------------------

Special details {#specialdetails}
===============

  ----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------
  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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ \> 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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 (Å^2^) {#tablewrapcoords}
==================================================================================================

  ------ -------------- -------- ------------ -------------------- ------------
         *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 (Å^2^) {#tablewrapadps}
=====================================

  ----- ------------- ------------- ------------- --------- -------------- ---------
        *U*^11^       *U*^22^       *U*^33^       *U*^12^   *U*^13^        *U*^23^
  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, °) {#tablewrapgeomlong}
===========================

  ------------------ ----------- ------------------- -----------
  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, °) {#tablewraphbondslong}
=============================

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

###### 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
