1-(2-Chloro-benzo-yl)-3-[4-(trifluoro-meth-oxy)phen-yl]urea.

The title compound, C(15)H(10)ClF(3)N(2)O(3), is considered to belong to a fourth generation of insecticides with properties such as high selectivity, low acute toxicity for mammals and high biological activity. The dihedral angle between the two benzene rings is 59.3 (2)°. Intra-molecular C-H⋯O and N-H⋯O hydrogen bonds are observed. Inter-molecular N-H⋯O hydrogen bonding generates a centrosymmetric dimer. The F atoms are disordered over two positions; the site occupancy factors are 0.52 and 0.48.

Related literature

For related literature, see: Allen et al. (1987 ▶); Wang et al. (1998 ▶); Qiu et al. (12004 ▶).

Experimental

Crystal data

C15H10ClF3N2O3

M = 358.70

Monoclinic,

a = 17.293 (4) Å

b = 8.2870 (17) Å

c = 11.073 (2) Å

β = 101.74 (3)°

V = 1553.6 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.30 mm−1

T = 298 (2) K

0.30 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.917, T max = 0.943

2946 measured reflections

2784 independent reflections

1906 reflections with I > 2σ(I)

R int = 0.012

3 standard reflections every 200 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.079

wR(F 2) = 0.186

S = 1.01

2784 reflections

209 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.58 e Å−3

Δρmin = −0.38 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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 datablocks global, I. DOI: 10.1107/S1600536808016462/kp2174sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808016462/kp2174Isup2.hkl

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

C15H10ClF3N2O3	F000 = 728
Mr = 358.70	Dx = 1.534 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 17.293 (4) Å	θ = 10–14º
b = 8.2870 (17) Å	µ = 0.30 mm−1
c = 11.073 (2) Å	T = 298 (2) K
β = 101.74 (3)º	Block, colourless
V = 1553.6 (6) Å3	0.30 × 0.20 × 0.20 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	Rint = 0.012
Radiation source: fine-focus sealed tube	θmax = 25.2º
Monochromator: graphite	θmin = 1.2º
T = 298(2) K	h = −20→20
ω/2θ scans	k = 0→9
Absorption correction: ψ scan(North et al., 1968)	l = 0→13
Tmin = 0.917, Tmax = 0.943	3 standard reflections
2946 measured reflections	every 200 reflections
2784 independent reflections	intensity decay: none
1906 reflections with I > 2σ(I)

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.079	H-atom parameters constrained
wR(F2) = 0.186	w = 1/[σ2(Fo2) + (0.06P)2 + 3P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
2784 reflections	Δρmax = 0.58 e Å−3
209 parameters	Δρmin = −0.37 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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	Occ. (<1)
Cl	0.39377 (8)	0.46678 (16)	0.93229 (10)	0.0767 (4)
F1	0.9765 (5)	0.8806 (12)	0.8631 (10)	0.147	0.52
F2	0.9962 (5)	0.7066 (11)	0.7283 (8)	0.131	0.52
F3	1.0673 (5)	0.7391 (10)	0.9039 (8)	0.127	0.52
F1'	0.9962 (6)	0.8363 (13)	0.9452 (9)	0.145	0.48
F2'	0.9788 (6)	0.7985 (12)	0.7564 (10)	0.140	0.48
F3'	1.0763 (4)	0.6519 (9)	0.8854 (7)	0.111	0.48
O1	0.9560 (2)	0.6074 (6)	0.8858 (4)	0.1185 (16)
O2	0.59902 (15)	0.5358 (4)	0.5609 (2)	0.0661 (8)
O3	0.50002 (17)	0.7159 (4)	0.8415 (3)	0.0733 (9)
N1	0.62777 (18)	0.6359 (4)	0.7569 (3)	0.0578 (9)
H1A	0.6061	0.6732	0.8145	0.069*
N2	0.49834 (18)	0.6012 (4)	0.6534 (3)	0.0552 (8)
H2A	0.4665	0.5691	0.5876	0.066*
C1	0.9996 (3)	0.7289 (13)	0.8574 (9)	0.146 (3)
C2	0.8720 (3)	0.6213 (7)	0.8485 (5)	0.0820 (15)
C3	0.8311 (3)	0.6917 (7)	0.9265 (5)	0.0849 (16)
H3A	0.8573	0.7353	1.0010	0.102*
C4	0.7488 (3)	0.6978 (6)	0.8930 (4)	0.0742 (13)
H4A	0.7194	0.7466	0.9445	0.089*
C5	0.7113 (2)	0.6298 (5)	0.7812 (3)	0.0570 (10)
C6	0.7545 (2)	0.5566 (6)	0.7047 (4)	0.0694 (12)
H6A	0.7294	0.5092	0.6310	0.083*
C7	0.8363 (3)	0.5553 (7)	0.7400 (5)	0.0802 (14)
H7A	0.8666	0.5088	0.6888	0.096*
C8	0.5786 (2)	0.5883 (5)	0.6510 (4)	0.0532 (10)
C9	0.4632 (2)	0.6571 (5)	0.7445 (4)	0.0527 (9)
C10	0.3755 (2)	0.6418 (5)	0.7208 (4)	0.0539 (10)
C11	0.3384 (2)	0.5638 (5)	0.8036 (4)	0.0561 (10)
C12	0.2570 (3)	0.5556 (6)	0.7844 (5)	0.0755 (13)
H12A	0.2327	0.5031	0.8410	0.091*
C13	0.2120 (3)	0.6263 (7)	0.6803 (5)	0.0842 (15)
H13A	0.1572	0.6227	0.6672	0.101*
C14	0.2478 (3)	0.7012 (7)	0.5968 (5)	0.0842 (15)
H14A	0.2172	0.7477	0.5267	0.101*
C15	0.3293 (3)	0.7087 (6)	0.6157 (4)	0.0687 (12)
H15A	0.3532	0.7588	0.5576	0.082*

	U11	U22	U33	U12	U13	U23
Cl	0.0925 (9)	0.0813 (8)	0.0561 (6)	0.0109 (7)	0.0145 (6)	0.0084 (6)
F1	0.147	0.147	0.147	0.000	0.030	0.000
F2	0.131	0.131	0.131	0.000	0.027	0.000
F3	0.127	0.127	0.127	0.000	0.026	0.000
F1'	0.145	0.145	0.145	0.000	0.030	0.000
F2'	0.140	0.140	0.140	0.000	0.029	0.000
F3'	0.111	0.111	0.111	0.000	0.023	0.000
O1	0.0479 (19)	0.170 (4)	0.123 (3)	−0.013 (2)	−0.017 (2)	0.038 (3)
O2	0.0487 (15)	0.092 (2)	0.0543 (16)	−0.0083 (15)	0.0024 (13)	−0.0147 (16)
O3	0.0656 (18)	0.083 (2)	0.0648 (18)	−0.0052 (16)	−0.0016 (15)	−0.0225 (17)
N1	0.0467 (18)	0.072 (2)	0.0491 (18)	−0.0096 (16)	−0.0039 (14)	−0.0009 (17)
N2	0.0502 (18)	0.064 (2)	0.0468 (17)	−0.0067 (16)	−0.0008 (14)	−0.0074 (16)
C1	0.025 (2)	0.234 (10)	0.168 (7)	−0.022 (4)	−0.005 (3)	0.020 (8)
C2	0.050 (3)	0.106 (4)	0.080 (3)	−0.017 (3)	−0.010 (2)	0.024 (3)
C3	0.056 (3)	0.126 (5)	0.063 (3)	−0.028 (3)	−0.012 (2)	0.007 (3)
C4	0.062 (3)	0.097 (4)	0.059 (3)	−0.023 (3)	−0.002 (2)	−0.001 (2)
C5	0.052 (2)	0.066 (3)	0.048 (2)	−0.014 (2)	−0.0026 (18)	0.0114 (19)
C6	0.049 (2)	0.089 (3)	0.063 (3)	−0.003 (2)	−0.004 (2)	0.002 (2)
C7	0.055 (3)	0.098 (4)	0.084 (3)	−0.001 (3)	0.006 (2)	0.004 (3)
C8	0.049 (2)	0.059 (2)	0.047 (2)	−0.0097 (19)	0.0009 (17)	−0.0001 (19)
C9	0.056 (2)	0.046 (2)	0.052 (2)	−0.0018 (18)	0.0009 (18)	0.0000 (18)
C10	0.053 (2)	0.047 (2)	0.058 (2)	0.0019 (18)	0.0017 (18)	−0.0064 (19)
C11	0.063 (2)	0.055 (3)	0.051 (2)	0.0033 (19)	0.0140 (19)	−0.0095 (19)
C12	0.066 (3)	0.082 (3)	0.083 (3)	0.002 (3)	0.027 (3)	−0.007 (3)
C13	0.057 (3)	0.098 (4)	0.097 (4)	0.007 (3)	0.013 (3)	−0.011 (3)
C14	0.071 (3)	0.088 (4)	0.082 (3)	0.022 (3)	−0.011 (3)	0.002 (3)
C15	0.061 (3)	0.077 (3)	0.064 (3)	0.005 (2)	0.003 (2)	0.012 (2)

Cl—C11	1.743 (4)	C3—C4	1.397 (6)
F1—C1	1.324 (12)	C3—H3A	0.9300
F2—C1	1.431 (11)	C4—C5	1.394 (6)
F3—C1	1.181 (10)	C4—H4A	0.9300
F1'—C1	1.327 (12)	C5—C6	1.379 (6)
F2'—C1	1.244 (11)	C6—C7	1.389 (6)
F3'—C1	1.447 (10)	C6—H6A	0.9300
O1—C1	1.334 (9)	C7—H7A	0.9300
O1—C2	1.432 (5)	C9—C10	1.490 (5)
O2—C8	1.205 (4)	C10—C11	1.382 (6)
O3—C9	1.233 (4)	C10—C15	1.386 (5)
N1—C8	1.360 (5)	C11—C12	1.381 (6)
N1—C5	1.416 (5)	C12—C13	1.383 (7)
N1—H1A	0.8600	C12—H12A	0.9300
N2—C9	1.361 (5)	C13—C14	1.362 (7)
N2—C8	1.398 (5)	C13—H13A	0.9300
N2—H2A	0.8600	C14—C15	1.384 (6)
C2—C7	1.350 (7)	C14—H14A	0.9300
C2—C3	1.354 (7)	C15—H15A	0.9300
C1—O1—C2	117.4 (5)	C5—C4—H4A	120.5
C8—N1—C5	126.0 (4)	C3—C4—H4A	120.5
C8—N1—H1A	117.0	C6—C5—C4	120.8 (4)
C5—N1—H1A	117.0	C6—C5—N1	123.9 (4)
C9—N2—C8	129.5 (3)	C4—C5—N1	115.2 (4)
C9—N2—H2A	115.3	C5—C6—C7	118.6 (4)
C8—N2—H2A	115.3	C5—C6—H6A	120.7
F3—C1—F2'	115.9 (9)	C7—C6—H6A	120.7
F3—C1—F1	101.2 (9)	C2—C7—C6	120.2 (5)
F2'—C1—F1	64.4 (8)	C2—C7—H7A	119.9
F3—C1—F1'	79.7 (8)	C6—C7—H7A	119.9
F2'—C1—F1'	107.4 (11)	O2—C8—N1	125.6 (4)
F1—C1—F1'	43.2 (6)	O2—C8—N2	120.2 (3)
F3—C1—O1	120.6 (9)	N1—C8—N2	114.2 (4)
F2'—C1—O1	119.2 (7)	O3—C9—N2	123.4 (4)
F1—C1—O1	121.0 (7)	O3—C9—C10	120.9 (4)
F1'—C1—O1	102.8 (8)	N2—C9—C10	115.7 (3)
F3—C1—F2	106.3 (8)	C11—C10—C15	118.6 (4)
F2'—C1—F2	38.4 (6)	C11—C10—C9	121.1 (3)
F1—C1—F2	102.6 (9)	C15—C10—C9	120.4 (4)
F1'—C1—F2	145.0 (11)	C12—C11—C10	121.1 (4)
O1—C1—F2	103.1 (8)	C12—C11—Cl	118.5 (4)
F3—C1—F3'	32.4 (5)	C10—C11—Cl	120.4 (3)
F2'—C1—F3'	118.7 (9)	C11—C12—C13	119.4 (5)
F1—C1—F3'	132.9 (8)	C11—C12—H12A	120.3
F1'—C1—F3'	108.3 (8)	C13—C12—H12A	120.3
O1—C1—F3'	98.9 (8)	C14—C13—C12	120.2 (5)
F2—C1—F3'	90.4 (7)	C14—C13—H13A	119.9
C7—C2—C3	122.6 (4)	C12—C13—H13A	119.9
C7—C2—O1	118.5 (5)	C13—C14—C15	120.5 (5)
C3—C2—O1	118.8 (5)	C13—C14—H14A	119.7
C2—C3—C4	118.8 (4)	C15—C14—H14A	119.7
C2—C3—H3A	120.6	C14—C15—C10	120.3 (5)
C4—C3—H3A	120.6	C14—C15—H15A	119.9
C5—C4—C3	119.0 (5)	C10—C15—H15A	119.9

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3	0.86	1.95	2.653 (4)	138
N2—H2A···O2i	0.86	2.00	2.851 (4)	172
C6—H6A···O2	0.93	2.24	2.838 (5)	121

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O3	0.86	1.95	2.653 (4)	138
N2—H2A⋯O2i	0.86	2.00	2.851 (4)	172
C6—H6A⋯O2	0.93	2.24	2.838 (5)	121

Symmetry code: (i) .