Benzyl N-(3-chloro-4-fluoro-phen-yl)carbamate.

The title compound, C(14)H(11)ClFNO(2), the phenyl ring (A), the chloro-fluoro-phenyl ring (B) and the central ketone O/C/O group (C) are not coplanar, with dihedral angles B/C = 31.6 (2), A/B = 21.3 (2) and A/C = 50.1 (2)°. The crystal packing is stabilized by N-H⋯O and C-H⋯O inter-actions.

Related literature

For the bioactivity of nitro­gen-containing heterocyclic compounds, see: Xuan et al. (2001 ▶). For applications of anilines, see: Bickoff et al.(1952 ▶); Riegel & Kent (2007 ▶); Kahl et al. (2007 ▶). For our ongoing research on the anti­microbial activity of heterocyclic mol­ecules, see: Awasthi, Mishra, Dixit et al. (2009 ▶); Awasthi, Mishra, Kumar et al. (2009 ▶); Mishra et al. (2008 ▶). For the synthesis, see: Brickner et al. (1996 ▶).

Experimental

Crystal data

C14H11ClFNO2

M = 279.69

Orthorhombic,

a = 10.4695 (16) Å

b = 9.0346 (11) Å

c = 28.361 (3) Å

V = 2682.6 (6) Å3

Z = 8

Cu Kα radiation

μ = 2.62 mm−1

T = 293 K

0.40 × 0.39 × 0.38 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.668, T max = 1.000

11782 measured reflections

2674 independent reflections

1547 reflections with I > 2σ(I)

R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.234

S = 1.01

2674 reflections

184 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.48 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811012608/zj2005sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811012608/zj2005Isup2.hkl

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

C14H11ClFNO2	F(000) = 1152
Mr = 279.69	Dx = 1.385 Mg m−3
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1370 reflections
a = 10.4695 (16) Å	θ = 3.1–74.8°
b = 9.0346 (11) Å	µ = 2.62 mm−1
c = 28.361 (3) Å	T = 293 K
V = 2682.6 (6) Å3	Block, white
Z = 8	0.40 × 0.39 × 0.38 mm

Oxford Diffraction Xcalibur Sapphire3 diffractometer	2674 independent reflections
Radiation source: fine-focus sealed tube	1547 reflections with I > 2σ(I)
graphite	Rint = 0.063
ω scans	θmax = 74.9°, θmin = 3.1°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	h = −12→11
Tmin = 0.668, Tmax = 1.000	k = −11→11
11782 measured reflections	l = −24→35

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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.234	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.1301P)2] where P = (Fo2 + 2Fc2)/3
2674 reflections	(Δ/σ)max = 0.050
184 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.48 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
F	0.4879 (3)	−0.1647 (3)	0.39260 (9)	0.1137 (11)
H1	0.292 (4)	−0.103 (5)	0.5867 (14)	0.078 (13)*
H8B	0.179 (4)	−0.457 (5)	0.6637 (16)	0.095 (14)*
H8A	0.322 (5)	−0.426 (5)	0.6868 (15)	0.090 (15)*
Cl1	0.30242 (15)	0.06343 (15)	0.41668 (4)	0.1034 (5)
O1	0.3368 (3)	−0.4275 (2)	0.59477 (8)	0.0683 (7)
N1	0.3282 (3)	−0.1806 (3)	0.57783 (10)	0.0619 (8)
O2	0.2655 (3)	−0.2593 (2)	0.64774 (8)	0.0616 (7)
C1	0.3700 (3)	−0.1824 (3)	0.53060 (11)	0.0542 (8)
C2	0.3225 (4)	−0.0749 (4)	0.50081 (12)	0.0619 (9)
H2	0.2637	−0.0063	0.5120	0.074*
C7	0.3126 (3)	−0.3012 (3)	0.60581 (12)	0.0544 (8)
C9	0.1806 (4)	−0.3126 (4)	0.72378 (12)	0.0612 (9)
C3	0.3623 (4)	−0.0687 (4)	0.45406 (12)	0.0669 (10)
C4	0.4493 (4)	−0.1710 (5)	0.43833 (14)	0.0741 (11)
C14	0.2263 (5)	−0.3472 (5)	0.76831 (13)	0.0799 (12)
H14	0.2967	−0.4092	0.7715	0.096*
C6	0.4595 (4)	−0.2837 (4)	0.51389 (14)	0.0691 (10)
H6	0.4934	−0.3551	0.5339	0.083*
C5	0.4974 (4)	−0.2771 (5)	0.46710 (16)	0.0777 (12)
H5	0.5559	−0.3454	0.4554	0.093*
C8	0.2409 (6)	−0.3783 (4)	0.68092 (14)	0.0727 (12)
C12	0.0646 (5)	−0.1989 (6)	0.80410 (16)	0.0924 (15)
H12	0.0258	−0.1606	0.8310	0.111*
C10	0.0767 (4)	−0.2206 (4)	0.72049 (15)	0.0736 (11)
H10	0.0448	−0.1956	0.6909	0.088*
C11	0.0188 (5)	−0.1646 (5)	0.76045 (16)	0.0879 (13)
H11	−0.0519	−0.1031	0.7576	0.106*
C13	0.1679 (6)	−0.2899 (6)	0.80796 (16)	0.1000 (16)
H13	0.1995	−0.3137	0.8377	0.120*

	U11	U22	U33	U12	U13	U23
F	0.134 (3)	0.132 (2)	0.0748 (16)	0.013 (2)	0.0481 (16)	−0.0009 (15)
Cl1	0.1209 (11)	0.1169 (11)	0.0724 (7)	0.0226 (8)	0.0116 (6)	0.0251 (6)
O1	0.092 (2)	0.0425 (13)	0.0708 (15)	−0.0037 (12)	0.0111 (13)	−0.0078 (10)
N1	0.084 (2)	0.0432 (15)	0.0582 (16)	0.0042 (14)	0.0088 (15)	−0.0015 (12)
O2	0.0882 (18)	0.0455 (12)	0.0511 (12)	0.0016 (11)	0.0080 (12)	−0.0006 (9)
C1	0.060 (2)	0.0470 (17)	0.0557 (17)	−0.0024 (14)	0.0038 (15)	−0.0008 (13)
C2	0.064 (2)	0.058 (2)	0.0635 (19)	0.0014 (16)	0.0106 (16)	−0.0055 (16)
C7	0.062 (2)	0.0425 (16)	0.0589 (17)	−0.0012 (14)	−0.0042 (15)	−0.0039 (14)
C9	0.071 (2)	0.0527 (19)	0.0600 (18)	−0.0037 (16)	0.0015 (17)	−0.0011 (15)
C3	0.071 (2)	0.071 (2)	0.0585 (19)	−0.0025 (18)	0.0092 (17)	0.0025 (17)
C4	0.077 (3)	0.083 (3)	0.063 (2)	−0.001 (2)	0.0237 (19)	−0.006 (2)
C14	0.086 (3)	0.094 (3)	0.060 (2)	0.009 (2)	−0.001 (2)	0.009 (2)
C6	0.066 (2)	0.060 (2)	0.081 (2)	0.0054 (17)	0.0158 (19)	−0.0007 (18)
C5	0.076 (3)	0.072 (2)	0.085 (3)	0.005 (2)	0.029 (2)	−0.009 (2)
C8	0.107 (4)	0.050 (2)	0.061 (2)	0.003 (2)	0.012 (2)	0.0048 (16)
C12	0.085 (3)	0.115 (4)	0.077 (3)	−0.010 (3)	0.025 (2)	−0.021 (3)
C10	0.079 (3)	0.071 (3)	0.071 (2)	−0.001 (2)	−0.006 (2)	−0.0047 (18)
C11	0.074 (3)	0.095 (3)	0.094 (3)	0.008 (2)	0.008 (2)	−0.020 (3)
C13	0.115 (4)	0.125 (4)	0.060 (2)	−0.006 (3)	0.003 (3)	−0.007 (2)

F—C4	1.360 (4)	C4—C5	1.356 (6)
Cl1—C3	1.715 (4)	C14—C13	1.381 (6)
O1—C7	1.210 (4)	C14—H14	0.9300
N1—C7	1.358 (4)	C6—C5	1.387 (6)
N1—C1	1.409 (4)	C6—H6	0.9300
N1—H1	0.83 (4)	C5—H5	0.9300
O2—C7	1.342 (4)	C8—H8B	1.08 (5)
O2—C8	1.452 (4)	C8—H8A	0.97 (5)
C1—C6	1.393 (5)	C12—C13	1.363 (7)
C1—C2	1.380 (5)	C12—C11	1.363 (6)
C2—C3	1.391 (4)	C12—H12	0.9300
C2—H2	0.9300	C10—C11	1.381 (6)
C9—C10	1.372 (6)	C10—H10	0.9300
C9—C14	1.386 (5)	C11—H11	0.9300
C9—C8	1.492 (5)	C13—H13	0.9300
C3—C4	1.372 (5)
C7—N1—C1	125.7 (3)	C5—C6—C1	119.3 (4)
C7—N1—H1	116 (3)	C5—C6—H6	120.3
C1—N1—H1	116 (3)	C1—C6—H6	120.3
C7—O2—C8	115.5 (3)	C4—C5—C6	120.0 (4)
C6—C1—C2	119.7 (3)	C4—C5—H5	120.0
C6—C1—N1	122.7 (3)	C6—C5—H5	120.0
C2—C1—N1	117.5 (3)	O2—C8—C9	108.0 (3)
C3—C2—C1	120.3 (3)	O2—C8—H8B	108 (2)
C3—C2—H2	119.8	C9—C8—H8B	112 (2)
C1—C2—H2	119.8	O2—C8—H8A	107 (3)
O1—C7—O2	124.9 (3)	C9—C8—H8A	114 (3)
O1—C7—N1	125.5 (3)	H8B—C8—H8A	108 (4)
O2—C7—N1	109.6 (3)	C13—C12—C11	119.3 (4)
C10—C9—C14	118.2 (4)	C13—C12—H12	120.4
C10—C9—C8	121.4 (4)	C11—C12—H12	120.4
C14—C9—C8	120.4 (4)	C11—C10—C9	120.9 (4)
C4—C3—C2	118.8 (4)	C11—C10—H10	119.5
C4—C3—Cl1	120.7 (3)	C9—C10—H10	119.5
C2—C3—Cl1	120.5 (3)	C12—C11—C10	120.5 (5)
C5—C4—F	119.5 (4)	C12—C11—H11	119.7
C5—C4—C3	121.8 (4)	C10—C11—H11	119.7
F—C4—C3	118.7 (4)	C12—C13—C14	120.8 (5)
C9—C14—C13	120.3 (5)	C12—C13—H13	119.6
C9—C14—H14	119.9	C14—C13—H13	119.6
C13—C14—H14	119.9
C7—N1—C1—C6	−34.6 (6)	C8—C9—C14—C13	−178.0 (5)
C7—N1—C1—C2	147.9 (4)	C2—C1—C6—C5	−1.5 (6)
C6—C1—C2—C3	0.9 (6)	N1—C1—C6—C5	−179.0 (4)
N1—C1—C2—C3	178.5 (3)	F—C4—C5—C6	179.5 (4)
C8—O2—C7—O1	−1.2 (6)	C3—C4—C5—C6	−0.4 (7)
C8—O2—C7—N1	178.5 (4)	C1—C6—C5—C4	1.2 (7)
C1—N1—C7—O1	2.8 (6)	C7—O2—C8—C9	−176.0 (3)
C1—N1—C7—O2	−176.9 (3)	C10—C9—C8—O2	50.9 (6)
C1—C2—C3—C4	−0.1 (6)	C14—C9—C8—O2	−131.2 (4)
C1—C2—C3—Cl1	179.3 (3)	C14—C9—C10—C11	−0.3 (6)
C2—C3—C4—C5	−0.2 (6)	C8—C9—C10—C11	177.7 (4)
Cl1—C3—C4—C5	−179.6 (4)	C13—C12—C11—C10	−0.4 (8)
C2—C3—C4—F	179.9 (4)	C9—C10—C11—C12	0.5 (7)
Cl1—C3—C4—F	0.5 (6)	C11—C12—C13—C14	0.1 (8)
C10—C9—C14—C13	0.0 (7)	C9—C14—C13—C12	0.1 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.83 (4)	2.09 (4)	2.906 (4)	164 (4)
C2—H2···O1i	0.93	2.67	3.414 (4)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.83 (4)	2.09 (4)	2.906 (4)	164 (4)
C2—H2⋯O1i	0.93	2.67	3.414 (4)	138

Symmetry code: (i) .