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

For amides as functional groups in biologically relevant mol­ecules, see: Allen *et al.* (2010[@bb1]). For the synthesis of this and similar compounds, see: Montalbetti *et al.* (2005[@bb4]).

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

 {#sec2.1}

### Crystal data {#sec2.1.1}

C~11~H~14~N~2~O~2~*M* *~r~* = 206.24Monoclinic,*a* = 8.0907 (10) Å*b* = 15.754 (2) Å*c* = 8.4529 (11) Åβ = 104.205 (2)°*V* = 1044.5 (2) Å^3^*Z* = 4Mo *K*α radiationμ = 0.09 mm^−1^*T* = 293 K0.29 × 0.21 × 0.19 mm

### Data collection {#sec2.1.2}

Bruker SMART APEX CCD diffractometerAbsorption correction: multi-scan (*SADABS*; Bruker, 2001[@bb2]) *T* ~min~ = 0.976, *T* ~max~ = 0.9815309 measured reflections2056 independent reflections1633 reflections with *I* \> 2σ(*I*)*R* ~int~ = 0.016

### Refinement {#sec2.1.3}

*R*\[*F* ^2^ \> 2σ(*F* ^2^)\] = 0.040*wR*(*F* ^2^) = 0.105*S* = 1.042056 reflections139 parametersH atoms treated by a mixture of independent and constrained refinementΔρ~max~ = 0.13 e Å^−3^Δρ~min~ = −0.18 e Å^−3^

 {#d5e407}

Data collection: *SMART* (Bruker, 2007[@bb3]); cell refinement: *SAINT* (Bruker, 2007[@bb3]); data reduction: *SAINT*; program(s) used to solve structure: *SHELXS97* (Sheldrick, 2008[@bb5]); program(s) used to refine structure: *SHELXL97* (Sheldrick, 2008[@bb5]); molecular graphics: *SHELXTL-Plus* (Sheldrick, 2008[@bb5]); software used to prepare material for publication: *SHELXL97*.

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

Crystal structure: contains datablocks global, I. DOI: [10.1107/S1600536810052207/su2236sup1.cif](http://dx.doi.org/10.1107/S1600536810052207/su2236sup1.cif)

Structure factors: contains datablocks I. DOI: [10.1107/S1600536810052207/su2236Isup2.hkl](http://dx.doi.org/10.1107/S1600536810052207/su2236Isup2.hkl)

Additional supplementary materials: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?su2236&file=su2236sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?su2236sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?su2236&checkcif=yes)

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: [SU2236](http://scripts.iucr.org/cgi-bin/sendsup?su2236)).

We thank the Natural Science Foundation of Shanxi (No. 2010011018) for support.

Comment
=======

Amides are one of the most important and prolific functional groups found in biologically relevant molecules (Allen *et al.*, 2010), which lead to the synthesis of *N*-phenylmorpholine-4-carboxamide. In this study, this new acetamide derivative was prepared and its structure is presented herein.

In the title compound all the bond lengths and angles are within normal ranges. The molecule of the title compound is markedly non-planar (Fig. 1). The urea-type moiety \[atoms N1,C7,O1,N2 - planar to within 0.0002 (13) Å\] is inclined to the phenyl ring by 42.88 (8) Å. The morpholine ring has a chair conformation.

In the crystal, intermolecular N---H···O hydrogen bonds link the molecules into infinite one-dimensional chains propagagting in \[001\] (see Fig. 2 and Table 1).

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

The title compound was synthesized according to the literature procedure (Montalbetti *et al.*, 2005). To a solution of isocyanatobenzene (1.19 g, 10 mmol) and morpholine (0.87 ml, 10 mmol) in CH~2~Cl~2~ (25 ml) was added triethylamine (1.20 ml, 10 mmol) in one portion. The reaction mixture was stirred at room temperature for 3 h, and then poured into ice-water (100 ml) under stirring. The combined organic phase was washed with water (3 × 20 ml), dried over MgSO~4~, and filtered. Colourless single crystals were obtained by slow evaporation of the filtrate at room temperature.

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

The NH H-atom was located in a difference Fourier map and was refined with *U*~iso~(H) = 1.2*U*~eq~(N). The C-bound H-atoms were positioned geometrically and refined as riding: C---H = 0.93 Å (CH) and 0.97 Å (CH~2~) with *U*~iso~(H) = 1.2*U*~eq~(C).

Figures
=======

![Molecular structure of the title molecule. Displacement ellipsoids are drawn at the 30% probability level.](e-67-0o225-fig1){#Fap1}

![View along the b-axis of the one-dimensional polymeric chain of the title compound formed by hydrogen bonding (green dashed lines). H-atoms not involved in hydrogen bonding have been omitted for clarity.](e-67-0o225-fig2){#Fap2}

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

  ------------------------- ---------------------------------------
  C~11~H~14~N~2~O~2~        *F*(000) = 440
  *M~r~* = 206.24           *D*~x~ = 1.312 Mg m^−3^
  Monoclinic, *P*2~1~/*c*   Mo *K*α radiation, λ = 0.71073 Å
  Hall symbol: -P 2ybc      Cell parameters from 5309 reflections
  *a* = 8.0907 (10) Å       θ = 2.6--26.1°
  *b* = 15.754 (2) Å        µ = 0.09 mm^−1^
  *c* = 8.4529 (11) Å       *T* = 293 K
  β = 104.205 (2)°          Block, colourless
  *V* = 1044.5 (2) Å^3^     0.29 × 0.21 × 0.19 mm
  *Z* = 4                   
  ------------------------- ---------------------------------------

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

  ------------------------------------------------------------ --------------------------------------
  Bruker SMART APEX CCD diffractometer                         2056 independent reflections
  Radiation source: fine-focus sealed tube                     1633 reflections with *I* \> 2σ(*I*)
  graphite                                                     *R*~int~ = 0.016
  ω scans                                                      θ~max~ = 26.1°, θ~min~ = 2.6°
  Absorption correction: multi-scan (*SADABS*; Bruker, 2001)   *h* = −8→9
  *T*~min~ = 0.976, *T*~max~ = 0.981                           *k* = −12→19
  5309 measured reflections                                    *l* = −10→9
  ------------------------------------------------------------ --------------------------------------

Refinement {#tablewraprefinementdatalong}
==========

  ------------------------------------- ------------------------------------------------------------------------------------------------
  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^) = 0.105                  H atoms treated by a mixture of independent and constrained refinement
  *S* = 1.04                            *w* = 1/\[σ^2^(*F*~o~^2^) + (0.051*P*)^2^ + 0.1766*P*\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  2056 reflections                      (Δ/σ)~max~ \< 0.001
  139 parameters                        Δρ~max~ = 0.13 e Å^−3^
  0 restraints                          Δρ~min~ = −0.18 e Å^−3^
  ------------------------------------- ------------------------------------------------------------------------------------------------

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

  -----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------
  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~   
  C1     0.32831 (18)   0.27851 (9)     0.53510 (15)   0.0363 (3)           
  C6     0.21670 (19)   0.23577 (9)     0.60820 (17)   0.0423 (4)           
  H006   0.2379         0.1796          0.6410         0.051\*              
  C2     0.2934 (2)     0.36162 (9)     0.48415 (18)   0.0446 (4)           
  H007   0.3679         0.3909          0.4358         0.054\*              
  C7     0.56729 (17)   0.17667 (8)     0.59477 (16)   0.0354 (3)           
  C11    0.79490 (19)   0.07168 (10)    0.61799 (19)   0.0466 (4)           
  H00A   0.7747         0.0651          0.7258         0.056\*              
  H00B   0.9098         0.0932          0.6306         0.056\*              
  C5     0.0740 (2)     0.27684 (11)    0.6320 (2)     0.0533 (4)           
  H010   0.0011         0.2486          0.6838         0.064\*              
  C9     0.6653 (2)     0.04917 (11)    0.2800 (2)     0.0532 (4)           
  H01A   0.5540         0.0256          0.2783         0.064\*              
  H01B   0.6755         0.0528          0.1683         0.064\*              
  C8     0.6786 (2)     0.13675 (10)    0.35298 (18)   0.0515 (4)           
  H01C   0.7849         0.1629          0.3450         0.062\*              
  H01D   0.5854         0.1716          0.2929         0.062\*              
  C10    0.7776 (2)     −0.01294 (10)   0.5331 (2)     0.0535 (4)           
  H01E   0.8650         −0.0511         0.5929         0.064\*              
  H01F   0.6674         −0.0373         0.5327         0.064\*              
  C4     0.0387 (2)     0.35911 (12)    0.5799 (2)     0.0633 (5)           
  H014   −0.0584        0.3862          0.5951         0.076\*              
  C3     0.1479 (2)     0.40080 (11)    0.5054 (2)     0.0587 (5)           
  H015   0.1236         0.4561          0.4687         0.070\*              
  N2     0.67253 (16)   0.13193 (8)     0.52338 (14)   0.0450 (3)           
  O1     0.55772 (13)   0.16176 (6)     0.73527 (11)   0.0438 (3)           
  O2     0.79327 (14)   −0.00542 (7)    0.36958 (15)   0.0565 (3)           
  N1     0.47270 (16)   0.23906 (8)     0.50123 (15)   0.0425 (3)           
  H1N    0.505 (2)      0.2590 (11)     0.421 (2)      0.051\*              
  ------ -------------- --------------- -------------- -------------------- --

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

  ----- ------------- ------------- ------------- ------------ ------------ -------------
        *U*^11^       *U*^22^       *U*^33^       *U*^12^      *U*^13^      *U*^23^
  C1    0.0432 (8)    0.0365 (7)    0.0307 (6)    0.0074 (6)   0.0117 (6)   −0.0014 (5)
  C6    0.0503 (9)    0.0360 (7)    0.0430 (8)    0.0046 (6)   0.0162 (7)   0.0020 (6)
  C2    0.0550 (9)    0.0384 (8)    0.0453 (8)    0.0065 (7)   0.0213 (7)   0.0050 (6)
  C7    0.0396 (7)    0.0314 (7)    0.0375 (7)    0.0000 (6)   0.0135 (6)   −0.0023 (6)
  C11   0.0415 (8)    0.0472 (9)    0.0516 (9)    0.0114 (7)   0.0123 (7)   0.0019 (7)
  C5    0.0504 (9)    0.0546 (10)   0.0616 (10)   0.0050 (8)   0.0265 (8)   0.0052 (8)
  C9    0.0503 (9)    0.0595 (10)   0.0538 (9)    0.0068 (8)   0.0202 (7)   −0.0086 (8)
  C8    0.0658 (11)   0.0506 (9)    0.0463 (8)    0.0153 (8)   0.0293 (8)   0.0033 (7)
  C10   0.0486 (9)    0.0437 (9)    0.0701 (11)   0.0086 (7)   0.0185 (8)   0.0023 (8)
  C4    0.0603 (11)   0.0606 (11)   0.0781 (12)   0.0253 (9)   0.0347 (9)   0.0106 (9)
  C3    0.0698 (11)   0.0421 (9)    0.0711 (11)   0.0222 (8)   0.0306 (9)   0.0134 (8)
  N2    0.0531 (8)    0.0446 (7)    0.0417 (7)    0.0159 (6)   0.0199 (6)   0.0024 (5)
  O1    0.0544 (6)    0.0438 (6)    0.0369 (5)    0.0098 (5)   0.0182 (5)   0.0034 (4)
  O2    0.0538 (7)    0.0500 (7)    0.0693 (8)    0.0108 (5)   0.0220 (6)   −0.0118 (6)
  N1    0.0525 (8)    0.0407 (7)    0.0411 (7)    0.0138 (6)   0.0245 (6)   0.0091 (5)
  ----- ------------- ------------- ------------- ------------ ------------ -------------

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

  --------------------- -------------- --------------------- --------------
  C1---C2               1.386 (2)      C5---H010             0.9300
  C1---C6               1.387 (2)      C9---O2               1.414 (2)
  C1---N1               1.4132 (18)    C9---C8               1.504 (2)
  C6---C5               1.380 (2)      C9---H01A             0.9700
  C6---H006             0.9300         C9---H01B             0.9700
  C2---C3               1.379 (2)      C8---N2               1.4553 (18)
  C2---H007             0.9300         C8---H01C             0.9700
  C7---O1               1.2315 (16)    C8---H01D             0.9700
  C7---N2               1.3559 (18)    C10---O2              1.424 (2)
  C7---N1               1.3711 (18)    C10---H01E            0.9700
  C11---N2              1.4601 (18)    C10---H01F            0.9700
  C11---C10             1.504 (2)      C4---C3               1.372 (2)
  C11---H00A            0.9700         C4---H014             0.9300
  C11---H00B            0.9700         C3---H015             0.9300
  C5---C4               1.376 (2)      N1---H1N              0.844 (17)
                                                             
  C2---C1---C6          119.46 (13)    H01A---C9---H01B      108.0
  C2---C1---N1          117.91 (13)    N2---C8---C9          109.95 (13)
  C6---C1---N1          122.52 (12)    N2---C8---H01C        109.7
  C5---C6---C1          119.76 (14)    C9---C8---H01C        109.7
  C5---C6---H006        120.1          N2---C8---H01D        109.7
  C1---C6---H006        120.1          C9---C8---H01D        109.7
  C3---C2---C1          119.86 (15)    H01C---C8---H01D      108.2
  C3---C2---H007        120.1          O2---C10---C11        111.67 (13)
  C1---C2---H007        120.1          O2---C10---H01E       109.3
  O1---C7---N2          121.67 (13)    C11---C10---H01E      109.3
  O1---C7---N1          122.31 (12)    O2---C10---H01F       109.3
  N2---C7---N1          116.02 (12)    C11---C10---H01F      109.3
  N2---C11---C10        110.11 (13)    H01E---C10---H01F     107.9
  N2---C11---H00A       109.6          C3---C4---C5          119.41 (15)
  C10---C11---H00A      109.6          C3---C4---H014        120.3
  N2---C11---H00B       109.6          C5---C4---H014        120.3
  C10---C11---H00B      109.6          C4---C3---C2          120.78 (15)
  H00A---C11---H00B     108.2          C4---C3---H015        119.6
  C4---C5---C6          120.69 (15)    C2---C3---H015        119.6
  C4---C5---H010        119.7          C7---N2---C8          126.22 (12)
  C6---C5---H010        119.7          C7---N2---C11         120.64 (12)
  O2---C9---C8          111.64 (14)    C8---N2---C11         113.14 (12)
  O2---C9---H01A        109.3          C9---O2---C10         110.01 (11)
  C8---C9---H01A        109.3          C7---N1---C1          124.79 (12)
  O2---C9---H01B        109.3          C7---N1---H1N         119.4 (12)
  C8---C9---H01B        109.3          C1---N1---H1N         115.7 (12)
                                                             
  C2---C1---C6---C5     −1.2 (2)       O1---C7---N2---C11    −8.0 (2)
  N1---C1---C6---C5     −177.35 (13)   N1---C7---N2---C11    172.05 (13)
  C6---C1---C2---C3     −0.5 (2)       C9---C8---N2---C7     −128.09 (16)
  N1---C1---C2---C3     175.89 (14)    C9---C8---N2---C11    51.77 (18)
  C1---C6---C5---C4     1.8 (2)        C10---C11---N2---C7   128.49 (15)
  O2---C9---C8---N2     −55.97 (18)    C10---C11---N2---C8   −51.38 (18)
  N2---C11---C10---O2   54.81 (17)     C8---C9---O2---C10    60.27 (17)
  C6---C5---C4---C3     −0.8 (3)       C11---C10---O2---C9   −59.74 (17)
  C5---C4---C3---C2     −0.9 (3)       O1---C7---N1---C1     −16.0 (2)
  C1---C2---C3---C4     1.5 (3)        N2---C7---N1---C1     163.93 (13)
  O1---C7---N2---C8     171.82 (14)    C2---C1---N1---C7     150.53 (14)
  N1---C7---N2---C8     −8.1 (2)       C6---C1---N1---C7     −33.2 (2)
  --------------------- -------------- --------------------- --------------

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

  ------------------ ------------ ------------ ------------- ---------------
  *D*---H···*A*      *D*---H      H···*A*      *D*···*A*     *D*---H···*A*
  N1---H1N···O1^i^   0.844 (17)   2.130 (18)   2.9543 (16)   165.3 (16)
  ------------------ ------------ ------------ ------------- ---------------

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

###### Hydrogen-bond geometry (Å, °)

  *D*---H⋯*A*        *D*---H      H⋯*A*        *D*⋯*A*       *D*---H⋯*A*
  ------------------ ------------ ------------ ------------- -------------
  N1---H1*N*⋯O1^i^   0.844 (17)   2.130 (18)   2.9543 (16)   165.3 (16)

Symmetry code: (i) .
