1-(4-Chloro­phen­yl)-3-(morpholin-4-yl)urea

Li, Y.-F.; Jiang, J.-H.

doi:10.1107/S1600536812012615

organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page o1219

doi:10.1107/S1600536812012615

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1-(4-Chlorophenyl)-3-(morpholin-4-yl)urea

Yu-Feng Li ^a ^* and Jin-He Jiang ^a

^aMicroscale Science Institute, Department of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: liyufeng8111@163.com

(Received 20 March 2012; accepted 23 March 2012; online 28 March 2012)

In the title molecule, C₁₁H₁₄ClN₃O₂, the morpholine ring has a chair conformation. In the crystal, pairs of molecules are linked into inversion dimers by N—H⋯O hydrogen bonds.

Related literature

For the medicinal properties of related compounds, see: Yang et al. (1997 ). For a related structure, see: Li (2011 ).

Experimental

Crystal data

C₁₁H₁₄ClN₃O₂
M_r = 255.70
Monoclinic, P 2₁ /c
a = 13.684 (3) Å
b = 9.3612 (19) Å
c = 9.758 (2) Å
β = 94.03 (3)°
V = 1246.8 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 293 K
0.22 × 0.20 × 0.19 mm

Data collection

Bruker SMART CCD diffractometer
11894 measured reflections
2857 independent reflections
1502 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.180
S = 1.17
2857 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2ⁱ	0.86	2.03	2.865 (3)	162
Symmetry code: (i) -x+3, -y, -z.

Data collection: SMART (Bruker 1997 ); cell refinement: SAINT (Bruker 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812012615/lh5438sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812012615/lh5438Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812012615/lh5438Isup3.cml

checkCIF report

Comment top

Some compounds which are related to the title compound have been shown to have medicinal properties (Yang et al., 1997). The molecular structure of the title compound is shown in Fig .1. The morpholine ring (C1-C4/O1/N1) has a chair conformation. The bond lengths and angles can be compared to those within a related structure (Li, 2011). In the crystal, pairs of molecules are linked into inversion dimers by N—H···O hydrogen bonds.

Related literature top

For the medicinal properties of related compounds, see: Yang et al. (1997). For a related structure, see: Li (2011).

Experimental top

A mixture of 4-aminomorpholine (0.08 mol), and (4-chlorophenyl)carbamic chloride (0.08 mol) was stirred in refluxing ethanol (18 ml) for 4 h to afford the title compound (0.064 mol, yield 80%). Colourless blocks of the title compound were obtained by recrystallization from ethanol at room temperature.

Structure description top

For the medicinal properties of related compounds, see: Yang et al. (1997). For a related structure, see: Li (2011).

Computing details top

Data collection: SMART (Bruker 1997); cell refinement: SAINT (Bruker 1997); data reduction: SAINT (Bruker 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The structure of the title compound showing 30% probability displacement ellipsoids.

1-(4-Chlorophenyl)-3-(morpholin-4-yl)urea top

Crystal data top

C₁₁H₁₄ClN₃O₂	F(000) = 536
M_r = 255.70	D_x = 1.362 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1502 reflections
a = 13.684 (3) Å	θ = 3.0–27.5°
b = 9.3612 (19) Å	µ = 0.30 mm⁻¹
c = 9.758 (2) Å	T = 293 K
β = 94.03 (3)°	Block, colorless
V = 1246.8 (4) Å³	0.22 × 0.20 × 0.19 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	1502 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.043
Graphite monochromator	θ_max = 27.5°, θ_min = 3.0°
φ and ω scans	h = −17→17
11894 measured reflections	k = −12→12
2857 independent reflections	l = −12→12

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.180	H-atom parameters constrained
S = 1.17	w = 1/[σ²(F_o²) + (0.085P)² + 0.0207P] where P = (F_o² + 2F_c²)/3
2857 reflections	(Δ/σ)_max < 0.001
154 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₁H₁₄ClN₃O₂	V = 1246.8 (4) Å³
M_r = 255.70	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.684 (3) Å	µ = 0.30 mm⁻¹
b = 9.3612 (19) Å	T = 293 K
c = 9.758 (2) Å	0.22 × 0.20 × 0.19 mm
β = 94.03 (3)°

Data collection top

Bruker SMART CCD diffractometer	1502 reflections with I > 2σ(I)
11894 measured reflections	R_int = 0.043
2857 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.180	H-atom parameters constrained
S = 1.17	Δρ_max = 0.20 e Å⁻³
2857 reflections	Δρ_min = −0.29 e Å⁻³
154 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

	x	y	z	U_iso*/U_eq
Cl1	0.92775 (5)	0.08842 (12)	0.30739 (8)	0.0988 (4)
O2	1.39233 (12)	0.0438 (2)	0.09026 (16)	0.0612 (5)
C6	1.18312 (16)	0.0784 (3)	0.0412 (2)	0.0493 (6)
N3	1.25450 (14)	0.0646 (2)	−0.0549 (2)	0.0561 (5)
H3A	1.2345	0.0708	−0.1403	0.067*
N1	1.35490 (13)	0.0024 (2)	−0.26930 (19)	0.0535 (5)
O1	1.35069 (15)	−0.0687 (2)	−0.55127 (17)	0.0697 (5)
N2	1.40369 (14)	0.0221 (3)	−0.1380 (2)	0.0656 (6)
H2A	1.4667	0.0212	−0.1292	0.079*
C5	1.35207 (17)	0.0425 (3)	−0.0260 (2)	0.0504 (6)
C8	1.1131 (2)	0.0212 (3)	0.2519 (3)	0.0674 (7)
H8A	1.1185	−0.0217	0.3381	0.081*
C11	1.09794 (16)	0.1525 (3)	−0.0004 (3)	0.0592 (6)
H11A	1.0931	0.1986	−0.0850	0.071*
C9	1.02870 (18)	0.0905 (3)	0.2072 (3)	0.0644 (7)
C10	1.02095 (18)	0.1582 (3)	0.0826 (3)	0.0672 (7)
H10A	0.9641	0.2076	0.0543	0.081*
C7	1.19009 (18)	0.0152 (3)	0.1684 (2)	0.0608 (7)
H7A	1.2474	−0.0321	0.1986	0.073*
C3	1.3409 (2)	0.0735 (3)	−0.5071 (3)	0.0734 (8)
H3B	1.2720	0.0954	−0.5020	0.088*
H3C	1.3669	0.1373	−0.5739	0.088*
C4	1.3938 (2)	0.0989 (3)	−0.3690 (3)	0.0666 (7)
H4A	1.4634	0.0822	−0.3741	0.080*
H4B	1.3847	0.1972	−0.3409	0.080*
C2	1.3146 (2)	−0.1633 (3)	−0.4542 (2)	0.0763 (8)
H2B	1.3226	−0.2609	−0.4849	0.092*
H2C	1.2451	−0.1462	−0.4478	0.092*
C1	1.3671 (2)	−0.1449 (3)	−0.3145 (3)	0.0709 (8)
H1A	1.3404	−0.2101	−0.2496	0.085*
H1B	1.4362	−0.1662	−0.3191	0.085*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0664 (5)	0.1530 (10)	0.0797 (6)	−0.0135 (5)	0.0244 (4)	−0.0336 (5)
O2	0.0541 (9)	0.0801 (13)	0.0483 (10)	0.0043 (8)	−0.0044 (8)	−0.0082 (8)
C6	0.0484 (12)	0.0545 (15)	0.0446 (12)	0.0017 (10)	0.0000 (10)	−0.0067 (10)
N3	0.0462 (10)	0.0747 (15)	0.0468 (11)	0.0059 (9)	−0.0007 (8)	−0.0015 (9)
N1	0.0532 (11)	0.0632 (14)	0.0438 (10)	0.0018 (9)	0.0020 (9)	−0.0021 (9)
O1	0.0918 (13)	0.0737 (13)	0.0449 (9)	0.0106 (10)	0.0143 (9)	0.0027 (9)
N2	0.0474 (11)	0.0996 (19)	0.0493 (11)	0.0054 (11)	−0.0004 (9)	−0.0114 (11)
C5	0.0500 (12)	0.0519 (15)	0.0488 (13)	0.0021 (10)	0.0005 (10)	−0.0025 (10)
C8	0.0644 (15)	0.090 (2)	0.0474 (13)	−0.0009 (15)	0.0025 (12)	−0.0051 (13)
C11	0.0540 (13)	0.0626 (17)	0.0605 (14)	0.0053 (12)	0.0002 (11)	0.0021 (13)
C9	0.0565 (14)	0.080 (2)	0.0576 (15)	−0.0081 (13)	0.0085 (12)	−0.0203 (14)
C10	0.0518 (13)	0.073 (2)	0.0767 (18)	0.0061 (13)	0.0022 (13)	−0.0102 (15)
C7	0.0557 (13)	0.0742 (19)	0.0519 (14)	0.0092 (13)	0.0002 (11)	−0.0006 (13)
C3	0.093 (2)	0.069 (2)	0.0590 (16)	0.0070 (16)	0.0062 (14)	0.0129 (14)
C4	0.0748 (17)	0.0613 (18)	0.0641 (16)	−0.0030 (13)	0.0083 (13)	0.0052 (13)
C2	0.111 (2)	0.0663 (19)	0.0530 (15)	−0.0077 (17)	0.0139 (15)	−0.0052 (13)
C1	0.103 (2)	0.0593 (17)	0.0501 (13)	0.0035 (16)	0.0059 (14)	0.0055 (12)

Geometric parameters (Å, º) top

Cl1—C9	1.748 (3)	C8—H8A	0.9300
O2—C5	1.226 (3)	C11—C10	1.374 (3)
C6—C7	1.373 (3)	C11—H11A	0.9300
C6—C11	1.392 (3)	C9—C10	1.369 (4)
C6—N3	1.407 (3)	C10—H10A	0.9300
N3—C5	1.361 (3)	C7—H7A	0.9300
N3—H3A	0.8600	C3—C4	1.503 (4)
N1—N2	1.414 (3)	C3—H3B	0.9700
N1—C4	1.456 (3)	C3—H3C	0.9700
N1—C1	1.461 (3)	C4—H4A	0.9700
O1—C3	1.409 (4)	C4—H4B	0.9700
O1—C2	1.411 (3)	C2—C1	1.505 (4)
N2—C5	1.356 (3)	C2—H2B	0.9700
N2—H2A	0.8600	C2—H2C	0.9700
C8—C9	1.369 (4)	C1—H1A	0.9700
C8—C7	1.377 (4)	C1—H1B	0.9700

C7—C6—C11	118.8 (2)	C6—C7—C8	120.7 (2)
C7—C6—N3	123.8 (2)	C6—C7—H7A	119.7
C11—C6—N3	117.3 (2)	C8—C7—H7A	119.7
C5—N3—C6	126.35 (19)	O1—C3—C4	112.0 (2)
C5—N3—H3A	116.8	O1—C3—H3B	109.2
C6—N3—H3A	116.8	C4—C3—H3B	109.2
N2—N1—C4	110.6 (2)	O1—C3—H3C	109.2
N2—N1—C1	109.9 (2)	C4—C3—H3C	109.2
C4—N1—C1	109.2 (2)	H3B—C3—H3C	107.9
C3—O1—C2	110.0 (2)	N1—C4—C3	109.0 (2)
C5—N2—N1	120.60 (19)	N1—C4—H4A	109.9
C5—N2—H2A	119.7	C3—C4—H4A	109.9
N1—N2—H2A	119.7	N1—C4—H4B	109.9
O2—C5—N2	121.4 (2)	C3—C4—H4B	109.9
O2—C5—N3	124.1 (2)	H4A—C4—H4B	108.3
N2—C5—N3	114.4 (2)	O1—C2—C1	111.6 (2)
C9—C8—C7	119.6 (3)	O1—C2—H2B	109.3
C9—C8—H8A	120.2	C1—C2—H2B	109.3
C7—C8—H8A	120.2	O1—C2—H2C	109.3
C10—C11—C6	120.6 (2)	C1—C2—H2C	109.3
C10—C11—H11A	119.7	H2B—C2—H2C	108.0
C6—C11—H11A	119.7	N1—C1—C2	108.9 (2)
C8—C9—C10	120.9 (2)	N1—C1—H1A	109.9
C8—C9—Cl1	119.9 (2)	C2—C1—H1A	109.9
C10—C9—Cl1	119.1 (2)	N1—C1—H1B	109.9
C9—C10—C11	119.4 (2)	C2—C1—H1B	109.9
C9—C10—H10A	120.3	H1A—C1—H1B	108.3
C11—C10—H10A	120.3

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2ⁱ	0.86	2.03	2.865 (3)	162

Symmetry code: (i) −x+3, −y, −z.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₄ClN₃O₂
M_r	255.70
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	13.684 (3), 9.3612 (19), 9.758 (2)
β (°)	94.03 (3)
V (Å³)	1246.8 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.22 × 0.20 × 0.19

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	11894, 2857, 1502
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.180, 1.17
No. of reflections	2857
No. of parameters	154
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.29

Computer programs: SMART (Bruker 1997), SAINT (Bruker 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2ⁱ	0.86	2.03	2.865 (3)	162

Symmetry code: (i) −x+3, −y, −z.

Acknowledgements

The authors would like to thank the Natural Science Foundation of Shandong Province (No. ZR2010BL025).

References

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