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

For the preparation of the title compound, see: Freire *et al.* (2011[@bb4]). For the use of this type of compound as LFA-1 (Lymphocyte Function-Associated Anti­gen-1) inhibitors, see: Baumann (2007[@bb1]). For related structures, see: Oliveira *et al.* (2012*a* [@bb6],*b* [@bb7]).

Experimental   {#sec2}
==============

 {#sec2.1}

### Crystal data   {#sec2.1.1}

C~14~H~15~NO~3~*M* *~r~* = 245.27Orthorhombic,*a* = 6.5007 (3) Å*b* = 13.6783 (7) Å*c* = 13.8382 (7) Å*V* = 1230.47 (11) Å^3^*Z* = 4Cu *K*α radiationμ = 0.77 mm^−1^*T* = 100 K0.31 × 0.13 × 0.13 mm

### Data collection   {#sec2.1.2}

Bruker Kappa APEXII DUO diffractometerAbsorption correction: numerical (*SADABS*; Bruker, 2010[@bb2]) *T* ~min~ = 0.924, *T* ~max~ = 1.00032528 measured reflections2219 independent reflections2203 reflections with *I* \> 2σ(*I*)*R* ~int~ = 0.034

### Refinement   {#sec2.1.3}

*R*\[*F* ^2^ \> 2σ(*F* ^2^)\] = 0.037*wR*(*F* ^2^) = 0.098*S* = 1.062219 reflections165 parametersH-atom parameters constrainedΔρ~max~ = 0.27 e Å^−3^Δρ~min~ = −0.23 e Å^−3^Absolute structure: Flack (1983[@bb3]) and Hooft *et al.* (2008[@bb5]); Hooft parameter = 0.01(2), 905 Bijvoet pairsFlack parameter: 0.1 (3)

 {#d5e449}

Data collection: *APEX2* (Bruker, 2010)[@bb2]; cell refinement: *SAINT* (Bruker, 2010[@bb2]); data reduction: *SAINT*; program(s) used to solve structure: *SHELXS97* (Sheldrick, 2008[@bb8]); program(s) used to refine structure: *SHELXL97* (Sheldrick, 2008[@bb8]); molecular graphics: *PLATON* (Spek, 2009[@bb9]); software used to prepare material for publication: *publCIF* (Westrip, 2010[@bb10]).

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

Crystal structure: contains datablock(s) I, global. DOI: [10.1107/S1600536812018223/pv2526sup1.cif](http://dx.doi.org/10.1107/S1600536812018223/pv2526sup1.cif)

Supplementary material file. DOI: [10.1107/S1600536812018223/pv2526Isup2.cml](http://dx.doi.org/10.1107/S1600536812018223/pv2526Isup2.cml)

Structure factors: contains datablock(s) I. DOI: [10.1107/S1600536812018223/pv2526Isup3.hkl](http://dx.doi.org/10.1107/S1600536812018223/pv2526Isup3.hkl)

Additional supplementary materials: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?pv2526&file=pv2526sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?pv2526sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?pv2526&checkcif=yes)

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: [PV2526](http://scripts.iucr.org/cgi-bin/sendsup?pv2526)).

The authors acknowledge the Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP), the Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) and the Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) for financial support. FLO and KRLF were supported by bursaries from CAPES and CNPq, respectively. KRLF is currently a FAPESP post-doctoral fellow. RA and FC are recipients of research grants from CNPq.

Comment
=======

The title compound (Fig. 1) is a new asymmetric benzyl-pyrrolizidinone which has been synthesized from a chiral Morita-Baylis-Hillman adduct. It belongs to a class of compounds with potential pharmacological properties as mediators of the LFA-1 (lymphocyte function-associated antigen 1) function, particularly as anti-inflammatory agents and for the treatment of autoimmune diseases (Baumann, 2007). It has three defined stereocenters and a double bond with *E* configuration. The five membered rings N1/C3/C2/C1/C7A and N1/C5/C6/C7/C7A of the pyrrolizine moiety exhibit C2- and C5-envelope conformations, respectively, with C2 and C5 atoms displaced from the mean-planes formed by the remaining rings atoms by 0.1468 (15) and 0.5405 (17) Å, respectively. The mean planes of these rings have a dihedral angle of 49.03 (10)°. The configuration of the double bond determined by X-ray crystallography confirms the two-dimensional-NOESY NMR analysis. The crystal structure is stabilized by intermolecular hydrogen bonds (Tab. 1 and Fig. 2).

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

The title compound was prepared using a synthetic sequence previously described (Freire *et al.*, 2011) and purified by flash silica gel column chromatography (CH~2~Cl~2~:MeOH -- solvent gradient: 100:0 to 95:05) to afford 0.14 g (as a white solid) in 76% yield, followed by recrystallization using the liquid-vapor saturation method. Subsequently, it was dissolved in ethanol and crystallized under the vapor pressure of ethyl ether (a less polar liquid), in a closed camera, thus allowing for the slow formation of good diffracting crystals.

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

The calculated Flack parameter was F = 0.1 (3) (Flack, 1983). Further analysis OF the absolute structure was performed with *PLATON* (Spek, 2009), using likelihood methods (Hooft *et al.*, 2008). The calculated value for the Hooft parameter was *y* = 0.01 (2), with a corresponding probability of 1x10^-100^ for an inverted structure. These results unequivocally indicate that the absolute structure has been correctly assigned. All H atoms were placed in calculated positions with O---H = 0.84 Å and C---H = 0.95, 0.99 and 1.00 Å for aryl, methylene and methyne H-atoms, respectively, and refined in the riding model approximation with *U*~iso~(H) = 1.5 *U*~eq~(O) or 1.2 *U*~eq~(C).

Figures
=======

![The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.](e-68-o1572-fig1){#Fap1}

![A view of the hydrogen bonding interactions (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity.](e-68-o1572-fig2){#Fap2}

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

  ------------------------------- ---------------------------------------
  C~14~H~15~NO~3~                 *D*~x~ = 1.324 Mg m^−3^
  *M~r~* = 245.27                 Cu *K*α radiation, λ = 1.54178 Å
  Orthorhombic, *P*2~1~2~1~2~1~   Cell parameters from 2219 reflections
  *a* = 6.5007 (3) Å              θ = 4.6--68.1°
  *b* = 13.6783 (7) Å             µ = 0.77 mm^−1^
  *c* = 13.8382 (7) Å             *T* = 100 K
  *V* = 1230.47 (11) Å^3^         Rectangular, colourless
  *Z* = 4                         0.31 × 0.13 × 0.13 mm
  *F*(000) = 520                  
  ------------------------------- ---------------------------------------

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

  ----------------------------------------------------------- --------------------------------------
  Bruker Kappa APEXII DUO diffractometer                      2219 independent reflections
  Radiation source: fine-focus sealed tube                    2203 reflections with *I* \> 2σ(*I*)
  Graphite monochromator                                      *R*~int~ = 0.034
  Bruker APEX CCD area--detector scans                        θ~max~ = 68.1°, θ~min~ = 4.6°
  Absorption correction: numerical (*SADABS*; Bruker, 2010)   *h* = −7→5
  *T*~min~ = 0.924, *T*~max~ = 1.000                          *k* = −16→16
  32528 measured reflections                                  *l* = −16→16
  ----------------------------------------------------------- --------------------------------------

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*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.037                              H-atom parameters constrained
  *wR*(*F*^2^) = 0.098                                             *w* = 1/\[σ^2^(*F*~o~^2^) + (0.0574*P*)^2^ + 0.2433*P*\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  *S* = 1.06                                                       (Δ/σ)~max~ \< 0.001
  2219 reflections                                                 Δρ~max~ = 0.27 e Å^−3^
  165 parameters                                                   Δρ~min~ = −0.23 e Å^−3^
  0 restraints                                                     Absolute structure: Flack (1983) and Hooft *et al.* (2008); Hooft parameter = 0.01(2), 905 Bijvoet pairs
  Primary atom site location: structure-invariant direct methods   Flack parameter: 0.1 (3)
  ---------------------------------------------------------------- ----------------------------------------------------------------------------------------------------------

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

  -----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------
  Experimental. \[α\]D^20^ + 40 (c 1, MeOH); IR (Film, ν~max~): 3427, 3195, 2940, 2855, 1668, 1634, 1493, 1424, 1268, 1156, 1067 cm^-1^; ^1^H NMR (400 MHz, CD3CN) δ 1.30 (m, *J* = 13.8, 9.1, 5.4 Hz, 1H, H-14 A), 2.38 (m, *J* = 13.8, 6.8 Hz, 1H, H-14B), 3.27 (dd, *J* = 12.3, 6.1 Hz, 1H, H-2 A), 3.56 (dd, *J* = 12.3, 3.3 Hz, 1H, H-2B), 3.69 (ddd, *J* = 9.1, 7.4, 1.8 Hz, 1H, H-10), 4.47 (qd, *J* = 6.1, 3.3 Hz, 1H, H-1 A), 4.91 (dd, *J* = 1.8 Hz, 1H, H-11), 7.35 (d, *J* = 2.1 Hz, 1H, H-5), 7.41 (m, 3H, Ph), 7.79 (m, 2H, Ph); ^13^C NMR (62.5 MHz, (CD~3~)~2~CO) δ 38.1, 52.1, 68.2, 70.1, 72.0, 129.2, 130.3, 131.3, 134.1, 134.2, 137.1, 172.1; HRMS (ESI-TOF) Calcd. for C~14~H~16~NO~3~ \[*M* + H\]^+^ 246.1130. Found 246.1168.
  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 *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^ \> σ(*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~   
  O1     0.2407 (3)      0.95636 (13)   0.17238 (19)   0.1020 (7)           
  H1     0.1725          1.0026         0.1962         0.153\*              
  O2     0.52812 (19)    0.71064 (10)   0.18954 (10)   0.0546 (3)           
  O3     −0.14247 (18)   0.65007 (11)   0.28956 (12)   0.0615 (4)           
  H3     −0.2555         0.6653         0.2643         0.092\*              
  N1     0.2098 (2)      0.75095 (9)    0.13314 (9)    0.0364 (3)           
  C6     0.1266 (3)      0.91174 (13)   0.09912 (14)   0.0478 (4)           
  H1A    0.0930          0.9587         0.0460         0.057\*              
  C5     0.2537 (3)      0.82646 (13)   0.06255 (12)   0.0465 (4)           
  H2A    0.2099          0.8063         −0.0030        0.056\*              
  H2B    0.4021          0.8428         0.0614         0.056\*              
  C3     0.3405 (2)      0.71615 (11)   0.20026 (12)   0.0364 (3)           
  C2     0.2186 (2)      0.68831 (11)   0.28681 (11)   0.0336 (3)           
  C4     0.3095 (2)      0.64180 (11)   0.36077 (11)   0.0381 (3)           
  H5     0.4483          0.6237         0.3490         0.046\*              
  C8     0.2326 (3)      0.61406 (11)   0.45626 (11)   0.0389 (4)           
  C13    0.3573 (3)      0.55253 (13)   0.51150 (13)   0.0498 (4)           
  H7     0.4864          0.5321         0.4864         0.060\*              
  C12    0.2964 (4)      0.52072 (15)   0.60216 (14)   0.0635 (6)           
  H8     0.3822          0.4779         0.6382         0.076\*              
  C11    0.1114 (4)      0.55125 (15)   0.63990 (13)   0.0631 (6)           
  H9     0.0687          0.5294         0.7019         0.076\*              
  C7A    −0.0026 (2)     0.75856 (12)   0.16618 (11)   0.0378 (3)           
  H10    −0.0881         0.7114         0.1283         0.045\*              
  C1     0.0020 (2)      0.72470 (11)   0.27237 (11)   0.0364 (3)           
  H11    −0.0253         0.7814         0.3162         0.044\*              
  C10    −0.0113 (4)     0.61354 (15)   0.58734 (13)   0.0603 (5)           
  H12    −0.1380         0.6353         0.6140         0.072\*              
  C9     0.0468 (3)      0.64509 (14)   0.49607 (13)   0.0498 (4)           
  H13    −0.0401         0.6879         0.4607         0.060\*              
  C7     −0.0656 (3)     0.86200 (15)   0.13809 (16)   0.0584 (5)           
  H14A   −0.1744         0.8603         0.0880         0.070\*              
  H14B   −0.1189         0.8977         0.1951         0.070\*              
  ------ --------------- -------------- -------------- -------------------- --

Atomic displacement parameters (Å^2^) {#tablewrapadps}
=====================================

  ----- ------------- ------------- ------------- -------------- -------------- --------------
        *U*^11^       *U*^22^       *U*^33^       *U*^12^        *U*^13^        *U*^23^
  O1    0.0789 (13)   0.0675 (10)   0.159 (2)     0.0143 (9)     −0.0431 (13)   −0.0432 (12)
  O2    0.0280 (6)    0.0762 (9)    0.0597 (7)    0.0084 (6)     0.0039 (5)     0.0184 (7)
  O3    0.0281 (6)    0.0713 (9)    0.0852 (10)   −0.0097 (6)    −0.0096 (6)    0.0430 (8)
  N1    0.0322 (6)    0.0392 (6)    0.0379 (6)    0.0041 (5)     −0.0002 (5)    0.0048 (5)
  C6    0.0442 (9)    0.0423 (8)    0.0570 (10)   0.0035 (7)     −0.0013 (8)    0.0138 (8)
  C5    0.0410 (10)   0.0574 (10)   0.0411 (8)    0.0042 (7)     0.0057 (7)     0.0141 (7)
  C3    0.0278 (8)    0.0392 (8)    0.0421 (8)    0.0037 (6)     −0.0011 (6)    0.0029 (6)
  C2    0.0292 (7)    0.0355 (7)    0.0361 (7)    −0.0007 (6)    −0.0034 (6)    0.0018 (6)
  C4    0.0309 (7)    0.0418 (8)    0.0418 (8)    −0.0003 (6)    −0.0042 (6)    0.0033 (7)
  C8    0.0451 (9)    0.0348 (7)    0.0367 (8)    −0.0039 (7)    −0.0068 (7)    −0.0012 (6)
  C13   0.0540 (11)   0.0485 (10)   0.0469 (9)    0.0012 (8)     −0.0085 (8)    0.0047 (8)
  C12   0.0888 (16)   0.0570 (11)   0.0448 (10)   −0.0003 (11)   −0.0128 (11)   0.0131 (9)
  C11   0.0951 (16)   0.0564 (11)   0.0377 (9)    −0.0114 (11)   0.0023 (10)    0.0015 (8)
  C7A   0.0255 (7)    0.0454 (8)    0.0425 (8)    −0.0020 (6)    −0.0051 (6)    0.0094 (6)
  C1    0.0283 (7)    0.0387 (7)    0.0420 (8)    0.0030 (6)     0.0001 (6)     0.0077 (6)
  C10   0.0782 (14)   0.0562 (10)   0.0464 (9)    0.0000 (11)    0.0177 (10)    −0.0107 (8)
  C9    0.0599 (11)   0.0458 (9)    0.0437 (9)    0.0058 (8)     0.0036 (8)     −0.0026 (7)
  C7    0.0440 (10)   0.0594 (11)   0.0717 (12)   0.0174 (8)     0.0097 (9)     0.0263 (10)
  ----- ------------- ------------- ------------- -------------- -------------- --------------

Geometric parameters (Å, º) {#tablewrapgeomlong}
===========================

  ----------------------- -------------- ---------------------- --------------
  O1---C6                 1.397 (3)      C8---C9                1.393 (3)
  O1---H1                 0.8400         C8---C13               1.397 (2)
  O2---C3                 1.231 (2)      C13---C12              1.386 (3)
  O3---C1                 1.4074 (19)    C13---H7               0.9500
  O3---H3                 0.8400         C12---C11              1.376 (4)
  N1---C3                 1.346 (2)      C12---H8               0.9500
  N1---C5                 1.450 (2)      C11---C10              1.375 (3)
  N1---C7A                1.458 (2)      C11---H9               0.9500
  C6---C5                 1.517 (2)      C7A---C7               1.524 (2)
  C6---C7                 1.521 (3)      C7A---C1               1.541 (2)
  C6---H1A                1.0000         C7A---H10              1.0000
  C5---H2A                0.9900         C1---H11               1.0000
  C5---H2B                0.9900         C10---C9               1.387 (3)
  C3---C2                 1.486 (2)      C10---H12              0.9500
  C2---C4                 1.342 (2)      C9---H13               0.9500
  C2---C1                 1.507 (2)      C7---H14A              0.9900
  C4---C8                 1.463 (2)      C7---H14B              0.9900
  C4---H5                 0.9500                                
                                                                
  C6---O1---H1            109.5          C8---C13---H7          119.4
  C1---O3---H3            109.5          C11---C12---C13        119.9 (2)
  C3---N1---C5            126.33 (14)    C11---C12---H8         120.1
  C3---N1---C7A           113.99 (12)    C13---C12---H8         120.1
  C5---N1---C7A           110.30 (12)    C10---C11---C12        119.62 (18)
  O1---C6---C5            106.77 (16)    C10---C11---H9         120.2
  O1---C6---C7            111.99 (19)    C12---C11---H9         120.2
  C5---C6---C7            102.82 (14)    N1---C7A---C7          103.95 (13)
  O1---C6---H1A           111.6          N1---C7A---C1          105.03 (12)
  C5---C6---H1A           111.6          C7---C7A---C1          121.85 (16)
  C7---C6---H1A           111.6          N1---C7A---H10         108.4
  N1---C5---C6            102.46 (13)    C7---C7A---H10         108.4
  N1---C5---H2A           111.3          C1---C7A---H10         108.4
  C6---C5---H2A           111.3          O3---C1---C2           111.20 (12)
  N1---C5---H2B           111.3          O3---C1---C7A          111.48 (13)
  C6---C5---H2B           111.3          C2---C1---C7A          104.12 (12)
  H2A---C5---H2B          109.2          O3---C1---H11          110.0
  O2---C3---N1            124.34 (16)    C2---C1---H11          110.0
  O2---C3---C2            127.58 (15)    C7A---C1---H11         110.0
  N1---C3---C2            108.08 (12)    C11---C10---C9         121.1 (2)
  C4---C2---C3            120.10 (14)    C11---C10---H12        119.5
  C4---C2---C1            132.00 (14)    C9---C10---H12         119.5
  C3---C2---C1            107.86 (12)    C10---C9---C8          120.10 (19)
  C2---C4---C8            131.40 (15)    C10---C9---H13         120.0
  C2---C4---H5            114.3          C8---C9---H13          120.0
  C8---C4---H5            114.3          C6---C7---C7A          106.55 (14)
  C9---C8---C13           118.05 (16)    C6---C7---H14A         110.4
  C9---C8---C4            125.05 (15)    C7A---C7---H14A        110.4
  C13---C8---C4           116.90 (16)    C6---C7---H14B         110.4
  C12---C13---C8          121.3 (2)      C7A---C7---H14B        110.4
  C12---C13---H7          119.4          H14A---C7---H14B       108.6
                                                                
  C3---N1---C5---C6       −109.15 (17)   C3---N1---C7A---C7     130.55 (16)
  C7A---N1---C5---C6      34.96 (17)     C5---N1---C7A---C7     −18.33 (18)
  O1---C6---C5---N1       81.68 (19)     C3---N1---C7A---C1     1.52 (18)
  C7---C6---C5---N1       −36.33 (18)    C5---N1---C7A---C1     −147.35 (13)
  C5---N1---C3---O2       −31.5 (3)      C4---C2---C1---O3      −52.6 (2)
  C7A---N1---C3---O2      −174.55 (16)   C3---C2---C1---O3      129.73 (14)
  C5---N1---C3---C2       147.63 (14)    C4---C2---C1---C7A     −172.77 (17)
  C7A---N1---C3---C2      4.63 (18)      C3---C2---C1---C7A     9.56 (16)
  O2---C3---C2---C4       −7.9 (3)       N1---C7A---C1---O3     −126.78 (14)
  N1---C3---C2---C4       172.96 (14)    C7---C7A---C1---O3     115.79 (17)
  O2---C3---C2---C1       170.10 (17)    N1---C7A---C1---C2     −6.80 (16)
  N1---C3---C2---C1       −9.04 (17)     C7---C7A---C1---C2     −124.23 (16)
  C3---C2---C4---C8       173.90 (15)    C12---C11---C10---C9   1.0 (3)
  C1---C2---C4---C8       −3.5 (3)       C11---C10---C9---C8    −0.3 (3)
  C2---C4---C8---C9       −10.3 (3)      C13---C8---C9---C10    −1.1 (3)
  C2---C4---C8---C13      170.38 (17)    C4---C8---C9---C10     179.60 (17)
  C9---C8---C13---C12     1.8 (3)        O1---C6---C7---C7A     −88.1 (2)
  C4---C8---C13---C12     −178.83 (17)   C5---C6---C7---C7A     26.1 (2)
  C8---C13---C12---C11    −1.1 (3)       N1---C7A---C7---C6     −5.9 (2)
  C13---C12---C11---C10   −0.3 (3)       C1---C7A---C7---C6     112.09 (18)
  ----------------------- -------------- ---------------------- --------------

Hydrogen-bond geometry (Å, º) {#tablewraphbondslong}
=============================

  ------------------ --------- --------- ------------- ---------------
  *D*---H···*A*      *D*---H   H···*A*   *D*···*A*     *D*---H···*A*
  O1---H1···O3^i^    0.84      2.04      2.776 (2)     147
  O3---H3···O2^ii^   0.84      1.85      2.6810 (17)   168
  ------------------ --------- --------- ------------- ---------------

Symmetry codes: (i) −*x*, *y*+1/2, −*z*+1/2; (ii) *x*−1, *y*, *z*.

###### Hydrogen-bond geometry (Å, °)

  *D*---H⋯*A*      *D*---H   H⋯*A*   *D*⋯*A*       *D*---H⋯*A*
  ---------------- --------- ------- ------------- -------------
  O1---H1⋯O3^i^    0.84      2.04    2.776 (2)     147
  O3---H3⋯O2^ii^   0.84      1.85    2.6810 (17)   168

Symmetry codes: (i) ; (ii) .
