N,N'-Bis(4-fluoro-phen-yl)urea.

The asymmetric unit of the title compound, C(13)H(10)F(2)N(2)O, contains one and a half N,N'-bis-(4-fluoro-phen-yl)urea mol-ecules. One of the mol-ecules has crystallographic twofold rotation symmetry. The benzene rings are twisted from each other by dihedral angles of 29.69 (6)° for the mol-ecule in a general position and 89.83 (6)° for the symmetry-generated mol-ecule. In the crystal structure, a pair of inter-molecular N-H⋯O hydrogen bonds link symmetry-related mol-ecules into chains along the b axis, forming R(2) (1)(6) ring motifs.

Related literature

For background to and the biological activity of bis-aryl­ureas, see: Khire et al. (2004 ▶); McDonnell et al. (2008 ▶); Francisco et al. (2004 ▶); Bigi et al. (1998 ▶). For the synthetic method, see: Sarveswari & Raja (2006 ▶). For a related structure, see: Jai-nhuknan et al. (1997 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C13H10F2N2O

M = 248.23

Monoclinic,

a = 67.541 (4) Å

b = 4.5750 (3) Å

c = 10.7098 (6) Å

β = 95.969 (2)°

V = 3291.4 (3) Å3

Z = 12

Mo Kα radiation

μ = 0.12 mm−1

T = 100 K

0.59 × 0.12 × 0.09 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.932, T max = 0.990

21915 measured reflections

5986 independent reflections

4304 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.159

S = 1.05

5986 reflections

257 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.69 e Å−3

Δρmin = −0.51 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810016399/lh5040sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810016399/lh5040Isup2.hkl

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

C13H10F2N2O	F(000) = 1536
Mr = 248.23	Dx = 1.503 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3635 reflections
a = 67.541 (4) Å	θ = 2.4–32.1°
b = 4.5750 (3) Å	µ = 0.12 mm−1
c = 10.7098 (6) Å	T = 100 K
β = 95.969 (2)°	Block, brown
V = 3291.4 (3) Å3	0.59 × 0.12 × 0.09 mm
Z = 12

Bruker APEXII DUO CCD area-detector diffractometer	5986 independent reflections
Radiation source: fine-focus sealed tube	4304 reflections with I > 2σ(I)
graphite	Rint = 0.050
φ and ω scans	θmax = 32.7°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −102→102
Tmin = 0.932, Tmax = 0.990	k = −6→6
21915 measured reflections	l = −16→16

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0899P)2 + 0.1948P] where P = (Fo2 + 2Fc2)/3
5986 reflections	(Δ/σ)max < 0.001
257 parameters	Δρmax = 0.69 e Å−3
0 restraints	Δρmin = −0.51 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
F1A	0.244179 (12)	0.5229 (2)	0.33663 (8)	0.02522 (19)
O1A	0.167883 (13)	0.5447 (2)	0.62122 (9)	0.0198 (2)
N1A	0.180685 (15)	0.9777 (2)	0.55991 (10)	0.0162 (2)
N2A	0.153498 (15)	0.9743 (3)	0.67129 (11)	0.0175 (2)
C1A	0.209007 (17)	0.6417 (3)	0.56407 (11)	0.0163 (2)
H1AA	0.2064	0.5746	0.6426	0.020*
C2A	0.225076 (17)	0.5295 (3)	0.50863 (12)	0.0180 (2)
H2AA	0.2332	0.3860	0.5486	0.022*
C3A	0.228714 (17)	0.6362 (3)	0.39263 (12)	0.0178 (2)
C4A	0.217243 (18)	0.8517 (3)	0.33077 (11)	0.0184 (2)
H4AA	0.2203	0.9236	0.2539	0.022*
C5A	0.200924 (18)	0.9591 (3)	0.38612 (11)	0.0172 (2)
H5AA	0.1928	1.1008	0.3451	0.021*
C6A	0.196784 (16)	0.8543 (3)	0.50280 (10)	0.0142 (2)
C7A	0.167422 (16)	0.8158 (3)	0.61783 (11)	0.0150 (2)
C8A	0.138631 (16)	0.8455 (3)	0.73842 (11)	0.0154 (2)
C9A	0.143599 (18)	0.6409 (3)	0.83227 (12)	0.0187 (2)
H9AA	0.1568	0.5838	0.8508	0.022*
C10A	0.128905 (18)	0.5208 (3)	0.89873 (12)	0.0207 (3)
H10A	0.1320	0.3818	0.9610	0.025*
C11A	0.109514 (19)	0.6143 (3)	0.86946 (12)	0.0209 (3)
C12A	0.104185 (18)	0.8202 (3)	0.77910 (12)	0.0219 (3)
H12A	0.0910	0.8809	0.7630	0.026*
C13A	0.118945 (18)	0.9362 (3)	0.71211 (12)	0.0193 (2)
H13A	0.1157	1.0745	0.6497	0.023*
F2A	0.095139 (12)	0.4948 (2)	0.93363 (9)	0.0309 (2)
F1B	0.072613 (12)	0.6424 (2)	1.16351 (8)	0.0289 (2)
O1B	0.0000	0.6661 (3)	0.7500	0.0262 (3)
N1B	0.013863 (16)	1.0982 (3)	0.82126 (11)	0.0193 (2)
C1B	0.024299 (18)	0.7613 (3)	0.99248 (12)	0.0200 (2)
H1BA	0.0112	0.6961	0.9919	0.024*
C2B	0.03907 (2)	0.6455 (3)	1.07851 (12)	0.0213 (3)
H2BA	0.0362	0.4998	1.1343	0.026*
C3B	0.058161 (18)	0.7529 (3)	1.07883 (12)	0.0210 (3)
C4B	0.063141 (18)	0.9679 (3)	0.99790 (12)	0.0212 (3)
H4BA	0.0761	1.0385	1.0018	0.025*
C5B	0.048369 (18)	1.0776 (3)	0.91008 (12)	0.0194 (2)
H5BA	0.0515	1.2200	0.8533	0.023*
C6B	0.028914 (17)	0.9741 (3)	0.90722 (12)	0.0170 (2)
C7B	0.0000	0.9380 (4)	0.7500	0.0181 (3)
H1NA	0.1792 (3)	1.157 (5)	0.5567 (17)	0.028 (5)*
H1NB	0.0136 (3)	1.289 (6)	0.8078 (19)	0.043 (6)*
H2NA	0.1535 (2)	1.160 (4)	0.6624 (16)	0.022 (4)*

	U11	U22	U33	U12	U13	U23
F1A	0.0210 (3)	0.0251 (5)	0.0312 (4)	0.0051 (3)	0.0105 (3)	−0.0019 (4)
O1A	0.0215 (4)	0.0090 (4)	0.0302 (5)	−0.0003 (3)	0.0084 (3)	−0.0003 (4)
N1A	0.0180 (4)	0.0082 (5)	0.0231 (5)	0.0010 (4)	0.0059 (4)	0.0014 (4)
N2A	0.0184 (4)	0.0094 (5)	0.0258 (5)	0.0014 (4)	0.0076 (4)	0.0010 (4)
C1A	0.0170 (5)	0.0144 (6)	0.0175 (5)	0.0004 (4)	0.0018 (4)	0.0011 (4)
C2A	0.0159 (5)	0.0147 (6)	0.0232 (6)	0.0025 (4)	0.0015 (4)	0.0012 (5)
C3A	0.0148 (5)	0.0171 (6)	0.0220 (5)	0.0005 (4)	0.0040 (4)	−0.0041 (5)
C4A	0.0195 (5)	0.0187 (6)	0.0174 (5)	−0.0004 (5)	0.0046 (4)	0.0001 (5)
C5A	0.0183 (5)	0.0151 (6)	0.0181 (5)	0.0007 (5)	0.0021 (4)	0.0006 (4)
C6A	0.0150 (4)	0.0106 (5)	0.0170 (5)	−0.0005 (4)	0.0017 (4)	−0.0015 (4)
C7A	0.0153 (4)	0.0119 (5)	0.0178 (5)	0.0006 (4)	0.0015 (4)	−0.0001 (4)
C8A	0.0157 (4)	0.0114 (5)	0.0195 (5)	−0.0011 (4)	0.0039 (4)	−0.0013 (4)
C9A	0.0178 (5)	0.0176 (6)	0.0205 (5)	−0.0003 (5)	0.0016 (4)	0.0011 (5)
C10A	0.0212 (5)	0.0207 (7)	0.0205 (6)	0.0006 (5)	0.0039 (4)	0.0035 (5)
C11A	0.0201 (5)	0.0200 (6)	0.0239 (6)	−0.0038 (5)	0.0078 (4)	−0.0015 (5)
C12A	0.0161 (5)	0.0215 (7)	0.0286 (6)	0.0010 (5)	0.0044 (4)	0.0005 (5)
C13A	0.0174 (5)	0.0168 (6)	0.0238 (6)	0.0019 (5)	0.0030 (4)	0.0020 (5)
F2A	0.0247 (4)	0.0319 (5)	0.0384 (5)	−0.0037 (4)	0.0150 (3)	0.0060 (4)
F1B	0.0284 (4)	0.0301 (5)	0.0263 (4)	0.0062 (4)	−0.0060 (3)	0.0031 (4)
O1B	0.0302 (7)	0.0107 (6)	0.0351 (7)	0.000	−0.0093 (6)	0.000
N1B	0.0177 (4)	0.0112 (5)	0.0280 (5)	−0.0008 (4)	−0.0017 (4)	0.0004 (4)
C1B	0.0194 (5)	0.0172 (6)	0.0235 (6)	−0.0020 (5)	0.0031 (4)	−0.0001 (5)
C2B	0.0275 (6)	0.0165 (6)	0.0200 (5)	−0.0009 (5)	0.0029 (4)	0.0015 (5)
C3B	0.0216 (5)	0.0203 (6)	0.0201 (5)	0.0039 (5)	−0.0024 (4)	−0.0008 (5)
C4B	0.0168 (5)	0.0223 (7)	0.0244 (6)	−0.0004 (5)	0.0011 (4)	−0.0012 (5)
C5B	0.0184 (5)	0.0180 (6)	0.0218 (5)	−0.0010 (5)	0.0022 (4)	0.0007 (5)
C6B	0.0171 (5)	0.0123 (6)	0.0213 (5)	0.0007 (4)	0.0010 (4)	−0.0016 (4)
C7B	0.0170 (7)	0.0136 (8)	0.0234 (8)	0.000	0.0005 (6)	0.000

F1A—C3A	1.3601 (13)	C10A—H10A	0.9300
O1A—C7A	1.2412 (15)	C11A—F2A	1.3611 (14)
N1A—C7A	1.3606 (15)	C11A—C12A	1.371 (2)
N1A—C6A	1.4190 (15)	C12A—C13A	1.3925 (17)
N1A—H1NA	0.83 (2)	C12A—H12A	0.9300
N2A—C7A	1.3602 (15)	C13A—H13A	0.9300
N2A—C8A	1.4223 (15)	F1B—C3B	1.3589 (15)
N2A—H2NA	0.85 (2)	O1B—C7B	1.244 (2)
C1A—C2A	1.3886 (16)	N1B—C7B	1.3593 (15)
C1A—C6A	1.3948 (17)	N1B—C6B	1.4173 (16)
C1A—H1AA	0.9300	N1B—H1NB	0.88 (3)
C2A—C3A	1.3805 (18)	C1B—C2B	1.3902 (18)
C2A—H2AA	0.9300	C1B—C6B	1.3921 (18)
C3A—C4A	1.3799 (18)	C1B—H1BA	0.9300
C4A—C5A	1.3941 (16)	C2B—C3B	1.3798 (19)
C4A—H4AA	0.9300	C2B—H2BA	0.9300
C5A—C6A	1.3937 (16)	C3B—C4B	1.376 (2)
C5A—H5AA	0.9300	C4B—C5B	1.3916 (18)
C8A—C9A	1.3888 (18)	C4B—H4BA	0.9300
C8A—C13A	1.3935 (16)	C5B—C6B	1.3942 (17)
C9A—C10A	1.3929 (17)	C5B—H5BA	0.9300
C9A—H9AA	0.9300	C7B—N1Bi	1.3593 (15)
C10A—C11A	1.3824 (18)
C7A—N1A—C6A	123.39 (11)	C9A—C10A—H10A	121.0
C7A—N1A—H1NA	118.3 (13)	F2A—C11A—C12A	118.92 (12)
C6A—N1A—H1NA	118.3 (13)	F2A—C11A—C10A	118.03 (12)
C7A—N2A—C8A	123.17 (11)	C12A—C11A—C10A	123.05 (12)
C7A—N2A—H2NA	118.4 (11)	C11A—C12A—C13A	118.42 (12)
C8A—N2A—H2NA	118.4 (11)	C11A—C12A—H12A	120.8
C2A—C1A—C6A	120.49 (11)	C13A—C12A—H12A	120.8
C2A—C1A—H1AA	119.8	C12A—C13A—C8A	120.09 (12)
C6A—C1A—H1AA	119.8	C12A—C13A—H13A	120.0
C3A—C2A—C1A	118.30 (11)	C8A—C13A—H13A	120.0
C3A—C2A—H2AA	120.8	C7B—N1B—C6B	123.66 (12)
C1A—C2A—H2AA	120.8	C7B—N1B—H1NB	116.0 (14)
F1A—C3A—C4A	118.63 (11)	C6B—N1B—H1NB	120.2 (14)
F1A—C3A—C2A	118.60 (11)	C2B—C1B—C6B	120.46 (11)
C4A—C3A—C2A	122.77 (11)	C2B—C1B—H1BA	119.8
C3A—C4A—C5A	118.48 (11)	C6B—C1B—H1BA	119.8
C3A—C4A—H4AA	120.8	C3B—C2B—C1B	118.17 (13)
C5A—C4A—H4AA	120.8	C3B—C2B—H2BA	120.9
C6A—C5A—C4A	120.08 (12)	C1B—C2B—H2BA	120.9
C6A—C5A—H5AA	120.0	F1B—C3B—C4B	118.73 (12)
C4A—C5A—H5AA	120.0	F1B—C3B—C2B	118.40 (13)
C5A—C6A—C1A	119.84 (11)	C4B—C3B—C2B	122.87 (12)
C5A—C6A—N1A	118.94 (11)	C3B—C4B—C5B	118.59 (12)
C1A—C6A—N1A	121.14 (10)	C3B—C4B—H4BA	120.7
O1A—C7A—N2A	122.47 (11)	C5B—C4B—H4BA	120.7
O1A—C7A—N1A	122.79 (11)	C4B—C5B—C6B	120.01 (13)
N2A—C7A—N1A	114.74 (11)	C4B—C5B—H5BA	120.0
C9A—C8A—C13A	120.06 (11)	C6B—C5B—H5BA	120.0
C9A—C8A—N2A	121.00 (10)	C1B—C6B—C5B	119.87 (12)
C13A—C8A—N2A	118.90 (11)	C1B—C6B—N1B	120.79 (11)
C8A—C9A—C10A	120.28 (11)	C5B—C6B—N1B	119.26 (12)
C8A—C9A—H9AA	119.9	O1B—C7B—N1Bi	122.63 (9)
C10A—C9A—H9AA	119.9	O1B—C7B—N1B	122.63 (8)
C11A—C10A—C9A	118.08 (12)	N1Bi—C7B—N1B	114.74 (17)
C11A—C10A—H10A	121.0

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1NA···O1Aii	0.83 (2)	2.08 (2)	2.8331 (13)	151.7 (18)
N1B—H1NB···O1Bii	0.89 (3)	2.02 (3)	2.8392 (18)	153.3 (19)
N2A—H2NA···O1Aii	0.855 (18)	2.080 (17)	2.8547 (16)	150.5 (13)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1NA⋯O1Ai	0.83 (2)	2.08 (2)	2.8331 (13)	151.7 (18)
N1B—H1NB⋯O1Bi	0.89 (3)	2.02 (3)	2.8392 (18)	153.3 (19)
N2A—H2NA⋯O1Ai	0.855 (18)	2.080 (17)	2.8547 (16)	150.5 (13)

Symmetry code: (i) .