Methyl N-(4-chloro-phen-yl)carbamate.

In the title compound, C(8)H(8)ClNO(2), the dihedral angle between the chloro-benzene ring and the side chain is 8.79 (11)°. In the crystal, mol-ecules 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 = 185.60

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.159

S = 1.06

1987 reflections

109 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.26 e Å−3

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811037123/hb6394sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811037123/hb6394Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811037123/hb6394Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C8H8ClNO2	F(000) = 384
Mr = 185.60	Dx = 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

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

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(Fo2) + (0.081P)2 + 0.0499P] where P = (Fo2 + 2Fc2)/3
1987 reflections	(Δ/σ)max < 0.001
109 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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

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

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) .