1-(2-Fluoro-benz-yl)-1-(2-fluoro-benz-yl-oxy)urea.

In the title hydroxy-urea derivative, C(15)H(14)F(2)N(2)O(2), the dihedral angle between the two benzene rings is 48.64 (19)°. The urea group forms dihedral angles of 48.1 (2) and 79.2 (2)° with the two benzene rings. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds occur, and further N-H⋯O links lead to chains of molecules.

Related literature

For geneal background, see: Krakoff et al. (1968 ▶); Young et al. (1967 ▶) and Yu et al. (1974 ▶). For related structures, see: Howard et al. (1967 ▶); Thiessen et al. (1978 ▶); Armagan et al. (1976 ▶); Berman & Kim (1967 ▶); Larsen et al. (1966 ▶); Nielsen et al. (1993 ▶).

Experimental

Crystal data

C15H14F2N2O2

M = 292.28

Monoclinic,

a = 5.196 (5) Å

b = 30.11 (3) Å

c = 9.059 (8) Å

β = 102.110 (16)°

V = 1386 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 296 (2) K

0.34 × 0.13 × 0.07 mm

Data collection

Bruker APEXII area-detector diffractometer

Absorption correction: none

8214 measured reflections

2416 independent reflections

1042 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.080

wR(F 2) = 0.260

S = 1.02

2416 reflections

166 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.37 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809000622/xu2472sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809000622/xu2472Isup2.hkl

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

C15H14F2N2O2	F(000) = 608
Mr = 292.28	Dx = 1.401 Mg m−3
Monoclinic, P21/c	Melting point: 414.0 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 5.196 (5) Å	Cell parameters from 1260 reflections
b = 30.11 (3) Å	θ = 2.4–19.3°
c = 9.059 (8) Å	µ = 0.11 mm−1
β = 102.110 (16)°	T = 296 K
V = 1386 (2) Å3	Needle, colourless
Z = 4	0.34 × 0.13 × 0.07 mm

Bruker APEXII area-detector diffractometer	1042 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.051
graphite	θmax = 25.0°, θmin = 2.4°
φ and ω scans	h = −6→6
8214 measured reflections	k = −35→35
2416 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)] = 0.080	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.260	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.14P)2] where P = (Fo2 + 2Fc2)/3
2416 reflections	(Δ/σ)max < 0.001
166 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.37 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
C10	0.2248 (6)	0.40316 (12)	0.5643 (3)	0.0675 (13)
C11	−0.0040 (7)	0.38153 (11)	0.4930 (4)	0.0829 (15)
C12	−0.1631 (6)	0.40007 (16)	0.3653 (4)	0.106 (2)
H12	−0.3162	0.3856	0.3175	0.127*
C13	−0.0935 (9)	0.44024 (17)	0.3089 (4)	0.118 (2)
H13	−0.2000	0.4526	0.2235	0.141*
C14	0.1352 (10)	0.46187 (12)	0.3803 (5)	0.119 (2)
H14	0.1818	0.4887	0.3426	0.142*
C15	0.2944 (7)	0.44333 (12)	0.5080 (5)	0.0938 (17)
H15	0.4474	0.4578	0.5557	0.113*
C3	0.1504 (7)	0.31233 (9)	0.9537 (4)	0.0677 (13)
C4	0.3952 (7)	0.29896 (13)	1.0354 (4)	0.0867 (16)
C5	0.4847 (6)	0.25614 (15)	1.0185 (5)	0.108 (2)
H5	0.6484	0.2472	1.0732	0.130*
C6	0.3294 (9)	0.22670 (10)	0.9199 (5)	0.1050 (19)
H6	0.3893	0.1980	0.9086	0.126*
C7	0.0846 (9)	0.24007 (11)	0.8383 (5)	0.113 (2)
H7	−0.0192	0.2204	0.7723	0.135*
C8	−0.0049 (6)	0.28289 (12)	0.8552 (4)	0.0964 (18)
H8	−0.1686	0.2918	0.8005	0.116*
C1	0.3969 (8)	0.43961 (14)	0.9001 (5)	0.0581 (11)
C2	0.0492 (10)	0.35829 (16)	0.9702 (6)	0.0767 (14)
H2A	−0.1322	0.3564	0.9812	0.092*
H2B	0.1512	0.3716	1.0615	0.092*
C9	0.3958 (9)	0.38360 (15)	0.7028 (5)	0.0675 (13)
H9A	0.3850	0.3515	0.6953	0.081*
H9B	0.5769	0.3919	0.7050	0.081*
F1	0.5413 (8)	0.32477 (14)	1.1264 (5)	0.1447 (16)
F2	−0.0789 (8)	0.34425 (11)	0.5430 (4)	0.1243 (13)
N1	0.3293 (6)	0.39708 (11)	0.8446 (4)	0.0594 (10)
N2	0.2206 (7)	0.46056 (11)	0.9610 (4)	0.0693 (11)
H2C	0.2563	0.4863	1.0015	0.083*
H2D	0.0704	0.4485	0.9601	0.083*
O1	0.0624 (5)	0.38636 (9)	0.8448 (3)	0.0635 (9)
O2	0.6157 (6)	0.45452 (10)	0.8966 (4)	0.0719 (10)

	U11	U22	U33	U12	U13	U23
C10	0.062 (3)	0.080 (3)	0.062 (3)	0.000 (3)	0.018 (2)	−0.019 (2)
C11	0.080 (4)	0.097 (4)	0.071 (4)	−0.010 (3)	0.014 (3)	−0.025 (3)
C12	0.095 (4)	0.139 (6)	0.080 (4)	−0.020 (4)	0.008 (4)	−0.029 (4)
C13	0.132 (6)	0.145 (6)	0.070 (4)	0.005 (5)	0.006 (4)	0.003 (4)
C14	0.141 (6)	0.123 (5)	0.084 (5)	−0.021 (5)	0.006 (4)	0.016 (4)
C15	0.092 (4)	0.111 (4)	0.080 (4)	−0.015 (3)	0.020 (3)	−0.001 (3)
C3	0.071 (3)	0.072 (3)	0.064 (3)	−0.015 (3)	0.021 (3)	0.002 (2)
C4	0.084 (4)	0.091 (4)	0.077 (4)	−0.011 (3)	−0.003 (3)	0.006 (3)
C5	0.106 (5)	0.111 (5)	0.102 (5)	0.010 (4)	0.007 (4)	0.036 (4)
C6	0.127 (5)	0.083 (4)	0.108 (5)	0.007 (4)	0.031 (4)	0.016 (4)
C7	0.106 (5)	0.097 (5)	0.121 (5)	0.000 (4)	−0.009 (4)	−0.008 (4)
C8	0.108 (4)	0.067 (4)	0.104 (4)	−0.001 (3)	0.000 (3)	−0.011 (3)
C1	0.050 (3)	0.064 (3)	0.059 (3)	0.004 (2)	0.008 (2)	−0.006 (2)
C2	0.075 (3)	0.082 (3)	0.076 (3)	−0.015 (3)	0.023 (3)	−0.006 (3)
C9	0.056 (3)	0.070 (3)	0.080 (3)	0.004 (2)	0.022 (2)	−0.021 (2)
F1	0.140 (3)	0.135 (3)	0.133 (3)	−0.026 (3)	−0.031 (2)	−0.013 (2)
F2	0.134 (3)	0.105 (3)	0.129 (3)	−0.038 (2)	0.016 (2)	−0.019 (2)
N1	0.049 (2)	0.061 (2)	0.069 (2)	−0.0016 (16)	0.0145 (17)	−0.0087 (18)
N2	0.054 (2)	0.063 (2)	0.096 (3)	−0.0041 (18)	0.027 (2)	−0.018 (2)
O1	0.0480 (17)	0.0676 (19)	0.077 (2)	−0.0041 (14)	0.0176 (15)	−0.0076 (15)
O2	0.0490 (18)	0.074 (2)	0.095 (2)	−0.0078 (16)	0.0216 (16)	−0.0186 (16)

C10—C11	1.3900	C5—H5	0.9300
C10—C15	1.3900	C6—C7	1.3900
C10—C9	1.497 (6)	C6—H6	0.9300
C11—F2	1.301 (4)	C7—C8	1.3900
C11—C12	1.3900	C7—H7	0.9300
C12—C13	1.3900	C8—H8	0.9300
C12—H12	0.9300	C1—O2	1.229 (5)
C13—C14	1.3900	C1—N2	1.324 (5)
C13—H13	0.9300	C1—N1	1.394 (5)
C14—C15	1.3900	C2—O1	1.429 (6)
C14—H14	0.9300	C2—H2A	0.9700
C15—H15	0.9300	C2—H2B	0.9700
C3—C4	1.3900	C9—N1	1.457 (6)
C3—C8	1.3900	C9—H9A	0.9700
C3—C2	1.499 (6)	C9—H9B	0.9700
C4—F1	1.264 (4)	N1—O1	1.424 (4)
C4—C5	1.3900	N2—H2C	0.8600
C5—C6	1.3900	N2—H2D	0.8600
C11—C10—C15	120.0	C5—C6—H6	120.0
C11—C10—C9	120.3 (3)	C6—C7—C8	120.0
C15—C10—C9	119.7 (3)	C6—C7—H7	120.0
F2—C11—C12	117.9 (3)	C8—C7—H7	120.0
F2—C11—C10	122.1 (3)	C7—C8—C3	120.0
C12—C11—C10	120.0	C7—C8—H8	120.0
C11—C12—C13	120.0	C3—C8—H8	120.0
C11—C12—H12	120.0	O2—C1—N2	124.2 (4)
C13—C12—H12	120.0	O2—C1—N1	119.4 (4)
C14—C13—C12	120.0	N2—C1—N1	116.4 (4)
C14—C13—H13	120.0	O1—C2—C3	113.0 (4)
C12—C13—H13	120.0	O1—C2—H2A	109.0
C13—C14—C15	120.0	C3—C2—H2A	109.0
C13—C14—H14	120.0	O1—C2—H2B	109.0
C15—C14—H14	120.0	C3—C2—H2B	109.0
C14—C15—C10	120.0	H2A—C2—H2B	107.8
C14—C15—H15	120.0	N1—C9—C10	114.9 (3)
C10—C15—H15	120.0	N1—C9—H9A	108.6
C4—C3—C8	120.0	C10—C9—H9A	108.6
C4—C3—C2	121.0 (3)	N1—C9—H9B	108.6
C8—C3—C2	119.0 (3)	C10—C9—H9B	108.6
F1—C4—C5	118.2 (4)	H9A—C9—H9B	107.5
F1—C4—C3	121.8 (4)	C1—N1—O1	112.3 (3)
C5—C4—C3	120.0	C1—N1—C9	119.0 (4)
C4—C5—C6	120.0	O1—N1—C9	110.4 (3)
C4—C5—H5	120.0	C1—N2—H2C	120.0
C6—C5—H5	120.0	C1—N2—H2D	120.0
C7—C6—C5	120.0	H2C—N2—H2D	120.0
C7—C6—H6	120.0	N1—O1—C2	110.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2C···O2i	0.86	2.05	2.910 (5)	174
N2—H2D···O2ii	0.86	2.32	3.079 (5)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2C⋯O2i	0.86	2.05	2.910 (5)	174
N2—H2D⋯O2ii	0.86	2.32	3.079 (5)	148

Symmetry codes: (i) ; (ii) .