Methyl N-(4-chloro­phen­yl)carbamate

Li, Y.-F.

doi:10.1107/S1600536811037123

organic compounds

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Volume 67| Part 10| October 2011| Page o2750

https://doi.org/10.1107/S1600536811037123

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Methyl N-(4-chlorophenyl)carbamate

Yu-Feng Li ^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 30 August 2011; accepted 13 September 2011; online 30 September 2011)

In the title compound, C₈H₈ClNO₂, the dihedral angle between the chlorobenzene ring and the side chain is 8.79 (11)°. In the crystal, molecules are linked by N—H⋯O hydrogen bonds into a C(4) chain propagating in the b-axis direction.

Related literature

For related structures, see: Li (2011a ,b ).

Experimental

Crystal data

C₈H₈ClNO₂
M_r = 185.60
Monoclinic, P 2₁ /c
a = 11.126 (2) Å
b = 9.833 (2) Å
c = 8.0076 (16) Å
β = 99.34 (3)°
V = 864.5 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.40 mm⁻¹
T = 293 K
0.23 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer
8281 measured reflections
1987 independent reflections
1011 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.159
S = 1.06
1987 reflections
109 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2ⁱ	0.86	2.22	3.069 (2)	168
Symmetry code: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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: https://doi.org/10.1107/S1600536811037123/hb6394sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811037123/hb6394Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811037123/hb6394Isup3.cml

checkCIF report

Related literature top

For related structures, see: Li (2011a,b).

Experimental top

A mixture of methanol (0.06 mol), and (4-chlorophenyl)carbamic chloride (0.06 mol) was stirred in refluxing ethanol (15 ml) for 4 h to afford the title compound (0.05 mol, yield 83%). Colourless blocks of the title compound were obtained by recrystallization from ethanol at room temperature.

Structure description top

For related structures, see: Li (2011a,b).

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 molecular structure of the title compound showing 50% probability displacement ellipsoids.

Methyl N-(4-chlorophenyl)carbamate top

Crystal data top

C₈H₈ClNO₂	F(000) = 384
M_r = 185.60	D_x = 1.426 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1987 reflections
a = 11.126 (2) Å	θ = 3.0–27.2°
b = 9.833 (2) Å	µ = 0.40 mm⁻¹
c = 8.0076 (16) Å	T = 293 K
β = 99.34 (3)°	Block, colorless
V = 864.5 (3) Å³	0.23 × 0.20 × 0.18 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	1011 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.036
Graphite monochromator	θ_max = 27.5°, θ_min = 3.3°
φ and ω scans	h = −14→13
8281 measured reflections	k = −12→12
1987 independent reflections	l = −10→10

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.159	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.081P)² + 0.0499P] where P = (F_o² + 2F_c²)/3
1987 reflections	(Δ/σ)_max < 0.001
109 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₈H₈ClNO₂	V = 864.5 (3) Å³
M_r = 185.60	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.126 (2) Å	µ = 0.40 mm⁻¹
b = 9.833 (2) Å	T = 293 K
c = 8.0076 (16) Å	0.23 × 0.20 × 0.18 mm
β = 99.34 (3)°

Data collection top

Bruker SMART CCD diffractometer	1011 reflections with I > 2σ(I)
8281 measured reflections	R_int = 0.036
1987 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.159	H-atom parameters constrained
S = 1.06	Δρ_max = 0.18 e Å⁻³
1987 reflections	Δρ_min = −0.26 e Å⁻³
109 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	0.51185 (8)	0.66723 (9)	0.21431 (13)	0.1092 (4)
N1	0.95328 (17)	0.52547 (19)	0.6982 (3)	0.0611 (5)
H1A	0.9543	0.4420	0.7304	0.073*
O2	1.06775 (16)	0.71949 (15)	0.7364 (2)	0.0699 (5)
C8	0.8511 (2)	0.56561 (19)	0.5821 (3)	0.0527 (6)
O1	1.12660 (16)	0.52441 (16)	0.8735 (2)	0.0749 (5)
C2	1.0498 (2)	0.6012 (2)	0.7656 (3)	0.0570 (6)
C7	0.8409 (2)	0.6894 (2)	0.4978 (3)	0.0628 (6)
H7A	0.9042	0.7521	0.5166	0.075*
C6	0.7360 (2)	0.7191 (2)	0.3855 (3)	0.0660 (7)
H6A	0.7294	0.8021	0.3290	0.079*
C5	0.6422 (2)	0.6283 (2)	0.3568 (3)	0.0665 (7)
C4	0.6513 (2)	0.5048 (2)	0.4395 (3)	0.0715 (7)
H4A	0.5878	0.4423	0.4195	0.086*
C3	0.7548 (2)	0.4750 (2)	0.5514 (3)	0.0644 (6)
H3A	0.7604	0.3920	0.6079	0.077*
C1	1.2359 (3)	0.5899 (3)	0.9546 (4)	0.0819 (8)
H1B	1.2841	0.5264	1.0282	0.123*
H1C	1.2151	0.6659	1.0196	0.123*
H1D	1.2817	0.6212	0.8703	0.123*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0837 (6)	0.1053 (7)	0.1253 (8)	−0.0005 (4)	−0.0225 (5)	0.0310 (5)
N1	0.0645 (12)	0.0440 (10)	0.0726 (14)	−0.0029 (8)	0.0044 (10)	0.0032 (8)
O2	0.0731 (11)	0.0436 (9)	0.0893 (13)	−0.0026 (7)	0.0018 (9)	−0.0033 (8)
C8	0.0568 (13)	0.0435 (11)	0.0582 (14)	0.0003 (9)	0.0104 (11)	−0.0046 (9)
O1	0.0764 (12)	0.0545 (9)	0.0866 (13)	−0.0024 (8)	−0.0085 (10)	0.0031 (8)
C2	0.0626 (14)	0.0463 (12)	0.0608 (15)	0.0040 (10)	0.0063 (11)	−0.0061 (10)
C7	0.0694 (16)	0.0509 (12)	0.0679 (16)	−0.0083 (10)	0.0106 (13)	0.0044 (10)
C6	0.0761 (17)	0.0530 (13)	0.0683 (17)	−0.0025 (11)	0.0105 (13)	0.0114 (11)
C5	0.0677 (16)	0.0597 (13)	0.0713 (17)	0.0040 (12)	0.0086 (13)	0.0046 (11)
C4	0.0665 (16)	0.0555 (13)	0.0897 (19)	−0.0079 (11)	0.0045 (14)	0.0013 (13)
C3	0.0683 (15)	0.0418 (11)	0.0811 (17)	−0.0030 (10)	0.0059 (13)	0.0041 (10)
C1	0.0753 (19)	0.0700 (16)	0.091 (2)	−0.0008 (13)	−0.0140 (15)	−0.0020 (14)

Geometric parameters (Å, º) top

Cl1—C5	1.736 (3)	C7—H7A	0.9300
N1—C2	1.345 (3)	C6—C5	1.364 (4)
N1—C8	1.404 (3)	C6—H6A	0.9300
N1—H1A	0.8600	C5—C4	1.379 (3)
O2—C2	1.209 (3)	C4—C3	1.371 (3)
C8—C3	1.385 (3)	C4—H4A	0.9300
C8—C7	1.388 (3)	C3—H3A	0.9300
O1—C2	1.345 (3)	C1—H1B	0.9600
O1—C1	1.435 (3)	C1—H1C	0.9600
C7—C6	1.384 (4)	C1—H1D	0.9600

C2—N1—C8	128.2 (2)	C6—C5—C4	120.1 (2)
C2—N1—H1A	115.9	C6—C5—Cl1	120.07 (19)
C8—N1—H1A	115.9	C4—C5—Cl1	119.9 (2)
C3—C8—C7	118.6 (2)	C3—C4—C5	119.4 (2)
C3—C8—N1	117.20 (19)	C3—C4—H4A	120.3
C7—C8—N1	124.2 (2)	C5—C4—H4A	120.3
C2—O1—C1	116.3 (2)	C4—C3—C8	121.5 (2)
O2—C2—O1	123.8 (2)	C4—C3—H3A	119.3
O2—C2—N1	126.9 (2)	C8—C3—H3A	119.3
O1—C2—N1	109.2 (2)	O1—C1—H1B	109.5
C6—C7—C8	119.7 (2)	O1—C1—H1C	109.5
C6—C7—H7A	120.2	H1B—C1—H1C	109.5
C8—C7—H7A	120.2	O1—C1—H1D	109.5
C5—C6—C7	120.8 (2)	H1B—C1—H1D	109.5
C5—C6—H6A	119.6	H1C—C1—H1D	109.5
C7—C6—H6A	119.6

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2ⁱ	0.86	2.22	3.069 (2)	168

Symmetry code: (i) −x+2, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₈H₈ClNO₂
M_r	185.60
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	11.126 (2), 9.833 (2), 8.0076 (16)
β (°)	99.34 (3)
V (Å³)	864.5 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.40
Crystal size (mm)	0.23 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8281, 1987, 1011
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.159, 1.06
No. of reflections	1987
No. of parameters	109
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.26

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
N1—H1A···O2ⁱ	0.86	2.22	3.069 (2)	168

Symmetry code: (i) −x+2, y−1/2, −z+3/2.

Acknowledgements

This study was supported by the Natural Science Foundation of Shandong Province (no. ZR2010BL025).

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Li, Y.-F. (2011a). Acta Cryst. E67, o1796. Web of Science CSD CrossRef IUCr Journals Google Scholar
Li, Y.-F. (2011b). Acta Cryst. E67, o2492. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar