organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

N-Phenyl­morpholine-4-carboxamide

aCollege of Chemistry and Chemical Engineering, Shanxi Datong University, Datong 037009, People's Republic of China
*Correspondence e-mail: ybsymsm@126.com

(Received 7 December 2010; accepted 13 December 2010; online 24 December 2010)

In the title compound, C11H14N2O2, the urea-type NC=ON moiety [planar to within 0.0002 (13) Å] is inclined to the phenyl ring by 42.88 (8) Å, and the morpholine ring has a chair conformation. In the crystal, inter­molecular N—H⋯O hydrogen bonds link the mol­ecules into infinite chains in [001].

Related literature

For amides as functional groups in biologically relevant mol­ecules, see: Allen et al. (2010[Allen, C. L., Burel, C. & Williams, J. M. J. (2010). Tetrahedron Lett. 20, 2724-2726.]). For the synthesis of this and similar compounds, see: Montalbetti et al. (2005[Montalbetti, C. & Falque, V. (2005). Tetrahedron Lett. 61, 10827-10852.]).

[Scheme 1]

Experimental

Crystal data
  • C11H14N2O2

  • Mr = 206.24

  • Monoclinic, P 21 /c

  • a = 8.0907 (10) Å

  • b = 15.754 (2) Å

  • c = 8.4529 (11) Å

  • β = 104.205 (2)°

  • V = 1044.5 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 293 K

  • 0.29 × 0.21 × 0.19 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.976, Tmax = 0.981

  • 5309 measured reflections

  • 2056 independent reflections

  • 1633 reflections with I > 2σ(I)

  • Rint = 0.016

Refinement
  • R[F2 > 2σ(F2)] = 0.040

  • wR(F2) = 0.105

  • S = 1.04

  • 2056 reflections

  • 139 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.13 e Å−3

  • Δρmin = −0.18 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1N⋯O1i 0.844 (17) 2.130 (18) 2.9543 (16) 165.3 (16)
Symmetry code: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL-Plus (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

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).

Related literature top

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

Experimental top

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 CH2Cl2 (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 MgSO4, and filtered. Colourless single crystals were obtained by slow evaporation of the filtrate at room temperature.

Refinement top

The NH H-atom was located in a difference Fourier map and was refined with Uiso(H) = 1.2Ueq(N). The C-bound H-atoms were positioned geometrically and refined as riding: C—H = 0.93 Å (CH) and 0.97 Å (CH2) with Uiso(H) = 1.2Ueq(C).

Structure description top

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).

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

Computing details top

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

Figures top
[Figure 1] Fig. 1. Molecular structure of the title molecule. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. 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.
N-Phenylmorpholine-4-carboxamide top
Crystal data top
C11H14N2O2F(000) = 440
Mr = 206.24Dx = 1.312 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5309 reflections
a = 8.0907 (10) Åθ = 2.6–26.1°
b = 15.754 (2) ŵ = 0.09 mm1
c = 8.4529 (11) ÅT = 293 K
β = 104.205 (2)°Block, colourless
V = 1044.5 (2) Å30.29 × 0.21 × 0.19 mm
Z = 4
Data collection top
Bruker SMART APEX CCD
diffractometer
2056 independent reflections
Radiation source: fine-focus sealed tube1633 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.016
ω scansθmax = 26.1°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 89
Tmin = 0.976, Tmax = 0.981k = 1219
5309 measured reflectionsl = 109
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.051P)2 + 0.1766P]
where P = (Fo2 + 2Fc2)/3
2056 reflections(Δ/σ)max < 0.001
139 parametersΔρmax = 0.13 e Å3
0 restraintsΔρmin = 0.18 e Å3
Crystal data top
C11H14N2O2V = 1044.5 (2) Å3
Mr = 206.24Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.0907 (10) ŵ = 0.09 mm1
b = 15.754 (2) ÅT = 293 K
c = 8.4529 (11) Å0.29 × 0.21 × 0.19 mm
β = 104.205 (2)°
Data collection top
Bruker SMART APEX CCD
diffractometer
2056 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
1633 reflections with I > 2σ(I)
Tmin = 0.976, Tmax = 0.981Rint = 0.016
5309 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.105H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.13 e Å3
2056 reflectionsΔρmin = 0.18 e Å3
139 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
C10.32831 (18)0.27851 (9)0.53510 (15)0.0363 (3)
C60.21670 (19)0.23577 (9)0.60820 (17)0.0423 (4)
H0060.23790.17960.64100.051*
C20.2934 (2)0.36162 (9)0.48415 (18)0.0446 (4)
H0070.36790.39090.43580.054*
C70.56729 (17)0.17667 (8)0.59477 (16)0.0354 (3)
C110.79490 (19)0.07168 (10)0.61799 (19)0.0466 (4)
H00A0.77470.06510.72580.056*
H00B0.90980.09320.63060.056*
C50.0740 (2)0.27684 (11)0.6320 (2)0.0533 (4)
H0100.00110.24860.68380.064*
C90.6653 (2)0.04917 (11)0.2800 (2)0.0532 (4)
H01A0.55400.02560.27830.064*
H01B0.67550.05280.16830.064*
C80.6786 (2)0.13675 (10)0.35298 (18)0.0515 (4)
H01C0.78490.16290.34500.062*
H01D0.58540.17160.29290.062*
C100.7776 (2)0.01294 (10)0.5331 (2)0.0535 (4)
H01E0.86500.05110.59290.064*
H01F0.66740.03730.53270.064*
C40.0387 (2)0.35911 (12)0.5799 (2)0.0633 (5)
H0140.05840.38620.59510.076*
C30.1479 (2)0.40080 (11)0.5054 (2)0.0587 (5)
H0150.12360.45610.46870.070*
N20.67253 (16)0.13193 (8)0.52338 (14)0.0450 (3)
O10.55772 (13)0.16176 (6)0.73527 (11)0.0438 (3)
O20.79327 (14)0.00542 (7)0.36958 (15)0.0565 (3)
N10.47270 (16)0.23906 (8)0.50123 (15)0.0425 (3)
H1N0.505 (2)0.2590 (11)0.421 (2)0.051*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0432 (8)0.0365 (7)0.0307 (6)0.0074 (6)0.0117 (6)0.0014 (5)
C60.0503 (9)0.0360 (7)0.0430 (8)0.0046 (6)0.0162 (7)0.0020 (6)
C20.0550 (9)0.0384 (8)0.0453 (8)0.0065 (7)0.0213 (7)0.0050 (6)
C70.0396 (7)0.0314 (7)0.0375 (7)0.0000 (6)0.0135 (6)0.0023 (6)
C110.0415 (8)0.0472 (9)0.0516 (9)0.0114 (7)0.0123 (7)0.0019 (7)
C50.0504 (9)0.0546 (10)0.0616 (10)0.0050 (8)0.0265 (8)0.0052 (8)
C90.0503 (9)0.0595 (10)0.0538 (9)0.0068 (8)0.0202 (7)0.0086 (8)
C80.0658 (11)0.0506 (9)0.0463 (8)0.0153 (8)0.0293 (8)0.0033 (7)
C100.0486 (9)0.0437 (9)0.0701 (11)0.0086 (7)0.0185 (8)0.0023 (8)
C40.0603 (11)0.0606 (11)0.0781 (12)0.0253 (9)0.0347 (9)0.0106 (9)
C30.0698 (11)0.0421 (9)0.0711 (11)0.0222 (8)0.0306 (9)0.0134 (8)
N20.0531 (8)0.0446 (7)0.0417 (7)0.0159 (6)0.0199 (6)0.0024 (5)
O10.0544 (6)0.0438 (6)0.0369 (5)0.0098 (5)0.0182 (5)0.0034 (4)
O20.0538 (7)0.0500 (7)0.0693 (8)0.0108 (5)0.0220 (6)0.0118 (6)
N10.0525 (8)0.0407 (7)0.0411 (7)0.0138 (6)0.0245 (6)0.0091 (5)
Geometric parameters (Å, º) top
C1—C21.386 (2)C5—H0100.9300
C1—C61.387 (2)C9—O21.414 (2)
C1—N11.4132 (18)C9—C81.504 (2)
C6—C51.380 (2)C9—H01A0.9700
C6—H0060.9300C9—H01B0.9700
C2—C31.379 (2)C8—N21.4553 (18)
C2—H0070.9300C8—H01C0.9700
C7—O11.2315 (16)C8—H01D0.9700
C7—N21.3559 (18)C10—O21.424 (2)
C7—N11.3711 (18)C10—H01E0.9700
C11—N21.4601 (18)C10—H01F0.9700
C11—C101.504 (2)C4—C31.372 (2)
C11—H00A0.9700C4—H0140.9300
C11—H00B0.9700C3—H0150.9300
C5—C41.376 (2)N1—H1N0.844 (17)
C2—C1—C6119.46 (13)H01A—C9—H01B108.0
C2—C1—N1117.91 (13)N2—C8—C9109.95 (13)
C6—C1—N1122.52 (12)N2—C8—H01C109.7
C5—C6—C1119.76 (14)C9—C8—H01C109.7
C5—C6—H006120.1N2—C8—H01D109.7
C1—C6—H006120.1C9—C8—H01D109.7
C3—C2—C1119.86 (15)H01C—C8—H01D108.2
C3—C2—H007120.1O2—C10—C11111.67 (13)
C1—C2—H007120.1O2—C10—H01E109.3
O1—C7—N2121.67 (13)C11—C10—H01E109.3
O1—C7—N1122.31 (12)O2—C10—H01F109.3
N2—C7—N1116.02 (12)C11—C10—H01F109.3
N2—C11—C10110.11 (13)H01E—C10—H01F107.9
N2—C11—H00A109.6C3—C4—C5119.41 (15)
C10—C11—H00A109.6C3—C4—H014120.3
N2—C11—H00B109.6C5—C4—H014120.3
C10—C11—H00B109.6C4—C3—C2120.78 (15)
H00A—C11—H00B108.2C4—C3—H015119.6
C4—C5—C6120.69 (15)C2—C3—H015119.6
C4—C5—H010119.7C7—N2—C8126.22 (12)
C6—C5—H010119.7C7—N2—C11120.64 (12)
O2—C9—C8111.64 (14)C8—N2—C11113.14 (12)
O2—C9—H01A109.3C9—O2—C10110.01 (11)
C8—C9—H01A109.3C7—N1—C1124.79 (12)
O2—C9—H01B109.3C7—N1—H1N119.4 (12)
C8—C9—H01B109.3C1—N1—H1N115.7 (12)
C2—C1—C6—C51.2 (2)O1—C7—N2—C118.0 (2)
N1—C1—C6—C5177.35 (13)N1—C7—N2—C11172.05 (13)
C6—C1—C2—C30.5 (2)C9—C8—N2—C7128.09 (16)
N1—C1—C2—C3175.89 (14)C9—C8—N2—C1151.77 (18)
C1—C6—C5—C41.8 (2)C10—C11—N2—C7128.49 (15)
O2—C9—C8—N255.97 (18)C10—C11—N2—C851.38 (18)
N2—C11—C10—O254.81 (17)C8—C9—O2—C1060.27 (17)
C6—C5—C4—C30.8 (3)C11—C10—O2—C959.74 (17)
C5—C4—C3—C20.9 (3)O1—C7—N1—C116.0 (2)
C1—C2—C3—C41.5 (3)N2—C7—N1—C1163.93 (13)
O1—C7—N2—C8171.82 (14)C2—C1—N1—C7150.53 (14)
N1—C7—N2—C88.1 (2)C6—C1—N1—C733.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.844 (17)2.130 (18)2.9543 (16)165.3 (16)
Symmetry code: (i) x, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC11H14N2O2
Mr206.24
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)8.0907 (10), 15.754 (2), 8.4529 (11)
β (°) 104.205 (2)
V3)1044.5 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.29 × 0.21 × 0.19
Data collection
DiffractometerBruker SMART APEX CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.976, 0.981
No. of measured, independent and
observed [I > 2σ(I)] reflections
5309, 2056, 1633
Rint0.016
(sin θ/λ)max1)0.618
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.105, 1.04
No. of reflections2056
No. of parameters139
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.13, 0.18

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL-Plus (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.844 (17)2.130 (18)2.9543 (16)165.3 (16)
Symmetry code: (i) x, y+1/2, z1/2.
 

Acknowledgements

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

References

First citationAllen, C. L., Burel, C. & Williams, J. M. J. (2010). Tetrahedron Lett. 20, 2724–2726.  Web of Science CrossRef Google Scholar
First citationBruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationBruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationMontalbetti, C. & Falque, V. (2005). Tetrahedron Lett. 61, 10827–10852.  CrossRef CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
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