N-(3,4-Difluoro-phen-yl)-N'-(2,5-di-methoxy-phen-yl)urea.

In the title compound, C(15)H(14)F(2)N(2)O(3), the dihedral angle between the benzene rings is 64.5 (1)°. One F atom is disordered over two meta positions, with occupancy factors of 0.72 and 0.28. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds involving two N-H and one C=O groups of the urea central fragment, leading to a supra-molecular chain along [011].

Related literature

For general background to the development of potent inhib­itory agents of tyrosinase and melanin formation used as whitening agents, see: Cabanes et al. (1994 ▶); Choi et al. (2010 ▶); Criton & Le Mellay-Hamon (2008 ▶); Germanas et al. (2007 ▶); Dawley & Flurkey (1993 ▶); Ha et al. (2007 ▶); Hong et al. (2008 ▶); Kwak et al. (2010 ▶); Lee et al. (2007 ▶); Nerya et al. (2003 ▶); Yi et al. (2009 ▶, 2010 ▶).

Experimental

Crystal data

C15H14F2N2O3

M = 308.28

Monoclinic,

a = 13.209 (2) Å

b = 12.0887 (18) Å

c = 9.0740 (12) Å

β = 104.990 (4)°

V = 1399.6 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 174 K

0.09 × 0.04 × 0.02 mm

Data collection

Bruker SMART CCD area-detector diffractometer

10104 measured reflections

2433 independent reflections

1211 reflections with I > 2σ(I)

R int = 0.120

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.145

S = 0.96

2433 reflections

218 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.26 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810032095/bh2300sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810032095/bh2300Isup2.hkl

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

C15H14F2N2O3	F(000) = 640
Mr = 308.28	Dx = 1.463 Mg m−3
Monoclinic, P21/c	Melting point: 454 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 13.209 (2) Å	Cell parameters from 398 reflections
b = 12.0887 (18) Å	θ = 3.0–18.6°
c = 9.0740 (12) Å	µ = 0.12 mm−1
β = 104.990 (4)°	T = 174 K
V = 1399.6 (4) Å3	Needle, colourless
Z = 4	0.09 × 0.04 × 0.02 mm

Bruker SMART CCD area-detector diffractometer	Rint = 0.120
Radiation source: fine-focus sealed tube	θmax = 25.3°, θmin = 1.6°
φ and ω scans	h = −15→14
10104 measured reflections	k = −12→14
2433 independent reflections	l = −4→10
1211 reflections with I > 2σ(I)

Refinement on F2	0 restraints
Least-squares matrix: full	0 constraints
R[F2 > 2σ(F2)] = 0.061	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.145	w = 1/[σ2(Fo2) + (0.0573P)2] where P = (Fo2 + 2Fc2)/3
S = 0.96	(Δ/σ)max < 0.001
2433 reflections	Δρmax = 0.25 e Å−3
218 parameters	Δρmin = −0.26 e Å−3

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.6480 (3)	0.4327 (3)	0.4129 (4)	0.0243 (9)
C2	0.5993 (3)	0.4687 (3)	0.2657 (4)	0.0278 (10)
H2	0.5991	0.4245	0.1818	0.033*
C3	0.5517 (3)	0.5705 (4)	0.2464 (4)	0.0351 (11)
H3	0.5189	0.5949	0.1484	0.042*	0.28
C4	0.5517 (3)	0.6365 (3)	0.3683 (5)	0.0354 (11)
C5	0.5984 (3)	0.6018 (4)	0.5137 (4)	0.0336 (11)
H5	0.5973	0.6468	0.5964	0.04*	0.72
C6	0.6469 (3)	0.5008 (3)	0.5371 (4)	0.0278 (10)
H6	0.6791	0.4775	0.6358	0.033*
F7	0.5055 (3)	0.6079 (3)	0.1088 (3)	0.0597 (11)	0.72
F7A	0.6007 (6)	0.6720 (7)	0.6227 (8)	0.041 (2)	0.28
F8	0.5028 (2)	0.7365 (2)	0.3447 (3)	0.0586 (8)
N9	0.6969 (2)	0.3289 (3)	0.4443 (3)	0.0274 (9)
H9	0.706 (3)	0.302 (3)	0.533 (4)	0.038 (12)*
C10	0.7429 (3)	0.2699 (3)	0.3512 (4)	0.0271 (10)
O11	0.74653 (19)	0.3012 (2)	0.2231 (2)	0.0301 (7)
N12	0.7839 (3)	0.1710 (3)	0.4127 (4)	0.0315 (9)
H12	0.775 (3)	0.151 (3)	0.492 (4)	0.036 (13)*
C13	0.8518 (3)	0.1019 (3)	0.3556 (4)	0.0259 (10)
C14	0.8499 (3)	−0.0108 (4)	0.3854 (4)	0.0295 (10)
C15	0.9184 (3)	−0.0817 (4)	0.3393 (4)	0.0347 (11)
H15	0.9177	−0.1569	0.3604	0.042*
C16	0.9883 (3)	−0.0401 (4)	0.2614 (4)	0.0346 (11)
H16	1.0341	−0.0875	0.2299	0.042*
C17	0.9893 (3)	0.0715 (4)	0.2313 (4)	0.0317 (10)
C18	0.9216 (3)	0.1432 (3)	0.2788 (4)	0.0295 (10)
H18	0.9233	0.2186	0.259	0.035*
O19	0.7767 (2)	−0.0423 (2)	0.4625 (3)	0.0381 (7)
C20	0.7657 (4)	−0.1587 (4)	0.4843 (5)	0.0496 (13)
H20A	0.7476	−0.1951	0.387	0.074*
H20B	0.7114	−0.1709	0.5353	0.074*
H20C	0.8307	−0.1879	0.5453	0.074*
O21	1.0554 (2)	0.1220 (2)	0.1555 (3)	0.0414 (8)
C22	1.1393 (3)	0.0546 (4)	0.1310 (4)	0.0423 (12)
H22A	1.18	0.0265	0.2271	0.063*
H22B	1.1833	0.0984	0.0846	0.063*
H22C	1.1107	−0.006	0.0651	0.063*

	U11	U22	U33	U12	U13	U23
C1	0.029 (2)	0.018 (2)	0.0284 (19)	−0.0011 (19)	0.0118 (16)	0.0004 (16)
C2	0.030 (2)	0.024 (3)	0.0296 (19)	−0.001 (2)	0.0088 (17)	−0.0009 (17)
C3	0.034 (3)	0.034 (3)	0.036 (2)	0.004 (2)	0.0063 (19)	0.007 (2)
C4	0.034 (3)	0.016 (3)	0.055 (3)	0.010 (2)	0.010 (2)	0.004 (2)
C5	0.030 (3)	0.028 (3)	0.045 (2)	0.000 (2)	0.0121 (19)	−0.006 (2)
C6	0.030 (2)	0.027 (3)	0.0278 (19)	−0.003 (2)	0.0082 (16)	−0.0031 (17)
F7	0.077 (3)	0.052 (3)	0.0428 (18)	0.022 (2)	0.0015 (17)	0.0155 (18)
F7A	0.050 (6)	0.031 (5)	0.050 (4)	0.006 (5)	0.025 (4)	−0.016 (4)
F8	0.066 (2)	0.0366 (18)	0.0715 (16)	0.0211 (15)	0.0138 (14)	0.0024 (13)
N9	0.039 (2)	0.025 (2)	0.0191 (16)	0.0072 (18)	0.0103 (14)	0.0042 (15)
C10	0.025 (3)	0.031 (3)	0.0251 (19)	−0.001 (2)	0.0065 (16)	−0.0030 (18)
O11	0.0381 (17)	0.0301 (18)	0.0248 (12)	0.0040 (14)	0.0133 (11)	0.0004 (11)
N12	0.043 (2)	0.025 (2)	0.0300 (18)	0.0083 (18)	0.0158 (16)	0.0063 (16)
C13	0.029 (3)	0.021 (3)	0.0270 (19)	0.004 (2)	0.0059 (17)	0.0016 (17)
C14	0.035 (3)	0.026 (3)	0.0265 (19)	−0.003 (2)	0.0066 (18)	0.0019 (18)
C15	0.046 (3)	0.020 (3)	0.037 (2)	0.003 (2)	0.008 (2)	−0.0021 (18)
C16	0.042 (3)	0.027 (3)	0.036 (2)	0.011 (2)	0.0121 (19)	−0.0048 (19)
C17	0.033 (3)	0.024 (3)	0.039 (2)	0.007 (2)	0.0094 (19)	0.0010 (19)
C18	0.037 (3)	0.018 (3)	0.034 (2)	0.001 (2)	0.0105 (18)	0.0033 (17)
O19	0.0450 (19)	0.0241 (19)	0.0492 (15)	−0.0003 (15)	0.0193 (14)	0.0043 (13)
C20	0.066 (3)	0.028 (3)	0.057 (3)	−0.012 (3)	0.019 (2)	0.003 (2)
O21	0.0436 (19)	0.035 (2)	0.0553 (16)	0.0122 (15)	0.0299 (14)	0.0078 (14)
C22	0.043 (3)	0.041 (3)	0.050 (2)	0.012 (2)	0.024 (2)	0.003 (2)

C1—C2	1.394 (5)	C13—C14	1.390 (5)
C1—C6	1.400 (5)	C14—O19	1.385 (4)
C1—N9	1.406 (5)	C14—C15	1.387 (5)
C2—C3	1.371 (5)	C15—C16	1.394 (5)
C2—H2	0.93	C15—H15	0.93
C3—C4	1.365 (5)	C16—C17	1.377 (5)
C3—F7	1.320 (5)	C16—H16	0.93
C4—F8	1.361 (4)	C17—O21	1.386 (5)
C4—C5	1.369 (5)	C17—C18	1.391 (5)
C5—C6	1.369 (5)	C18—H18	0.93
C5—H5	0.93	O19—C20	1.434 (5)
C6—H6	0.93	C20—H20A	0.96
N9—C10	1.362 (4)	C20—H20B	0.96
N9—H9	0.84 (4)	C20—H20C	0.96
C10—O11	1.235 (4)	O21—C22	1.439 (4)
C10—N12	1.370 (5)	C22—H22A	0.96
N12—C13	1.418 (5)	C22—H22B	0.96
N12—H12	0.80 (4)	C22—H22C	0.96
C13—C18	1.385 (5)
C2—C1—C6	119.3 (4)	C14—C13—N12	117.5 (4)
C2—C1—N9	123.2 (3)	O19—C14—C15	125.3 (4)
C6—C1—N9	117.5 (3)	O19—C14—C13	114.7 (4)
C3—C2—C1	119.0 (3)	C15—C14—C13	120.1 (4)
C3—C2—H2	120.5	C14—C15—C16	120.0 (4)
C1—C2—H2	120.5	C14—C15—H15	120
F7—C3—C4	118.0 (4)	C16—C15—H15	120
F7—C3—C2	120.9 (4)	C17—C16—C15	119.7 (4)
C4—C3—C2	121.1 (4)	C17—C16—H16	120.2
C4—C3—H3	119.4	C15—C16—H16	120.2
C2—C3—H3	119.4	C16—C17—O21	124.7 (4)
F8—C4—C3	119.4 (4)	C16—C17—C18	120.7 (4)
F8—C4—C5	120.1 (4)	O21—C17—C18	114.6 (4)
C3—C4—C5	120.5 (4)	C13—C18—C17	119.7 (4)
C6—C5—C4	119.9 (4)	C13—C18—H18	120.1
C6—C5—H5	120	C17—C18—H18	120.1
C4—C5—H5	120	C14—O19—C20	116.7 (3)
C5—C6—C1	120.1 (4)	O19—C20—H20A	109.5
C5—C6—H6	119.9	O19—C20—H20B	109.5
C1—C6—H6	119.9	H20A—C20—H20B	109.5
C10—N9—C1	126.7 (3)	O19—C20—H20C	109.5
C10—N9—H9	115 (3)	H20A—C20—H20C	109.5
C1—N9—H9	118 (3)	H20B—C20—H20C	109.5
O11—C10—N9	123.7 (4)	C17—O21—C22	115.9 (3)
O11—C10—N12	122.9 (4)	O21—C22—H22A	109.5
N9—C10—N12	113.4 (3)	O21—C22—H22B	109.5
C10—N12—C13	125.9 (3)	H22A—C22—H22B	109.5
C10—N12—H12	120 (3)	O21—C22—H22C	109.5
C13—N12—H12	114 (3)	H22A—C22—H22C	109.5
C18—C13—C14	119.9 (4)	H22B—C22—H22C	109.5
C18—C13—N12	122.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N9—H9···O11i	0.84 (4)	2.09 (4)	2.907 (4)	163 (4)
N12—H12···O11i	0.80 (4)	2.30 (4)	3.002 (4)	147 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N9—H9⋯O11i	0.84 (4)	2.09 (4)	2.907 (4)	163 (4)
N12—H12⋯O11i	0.80 (4)	2.30 (4)	3.002 (4)	147 (4)

Symmetry code: (i) .