N-Phenyl­morpholine-4-carboxamide

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].

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.040
• wR factor = 0.105
• Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT414_ALERT_2_C Short Intra D-H..H-X       H1N    ..  H01D    ..       1.96 Ang.
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600          7

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        293 K
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........         13

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. 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).

Related literature

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).

S2. 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 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.

S3. Refinement

The NH H-atom was located in a difference Fourier map and was refined with U_iso(H) = 1.2U_eq(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 U_iso(H) = 1.2U_eq(C).

Computing details

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

	Fig. 1. Molecular structure of the title molecule. Displacement ellipsoids are drawn at the 30% probability level.
	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

Crystal data

C11H14N2O2	F(000) = 440
Mr = 206.24	Dx = 1.312 Mg m^−3
Monoclinic, P21/c	Mo Kα 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

Bruker SMART APEX CCD diffractometer	2056 independent reflections
Radiation source: fine-focus sealed tube	1633 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
ω scans	θmax = 26.1°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −8→9
Tmin = 0.976, Tmax = 0.981	k = −12→19
5309 measured reflections	l = −10→9

Refinement

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(Fo^2) + (0.051P)^2 + 0.1766P] where P = (Fo^2 + 2Fc^2)/3
2056 reflections	(Δ/σ)max < 0.001
139 parameters	Δρmax = 0.13 e Å^−3
0 restraints	Δρmin = −0.18 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	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, º)

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, º)

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 code: (i) x, −y+1/2, z−1/2.