1-(2-Chloro­benzo­yl)-3-[4-(trifluoro­meth­oxy)phen­yl]urea

Liu, Y.; Li, F.; Yin, L.; Yu, D.

doi:10.1107/S1600536808016462

1-(2-Chlorobenzoyl)-3-[4-(trifluoromethoxy)phenyl]urea

The title compound, C₁₅H₁₀ClF₃N₂O₃, 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)°. Intramolecular C—H

O and N—H

O hydrogen bonds are observed. Intermolecular 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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808016462/kp2174sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536808016462/kp2174Isup2.hkl Contains datablock I

CCDC reference: 696498

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.007 Å
Disorder in main residue
R factor = 0.079
wR factor = 0.186
Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT213_ALERT_2_C Atom C1      has ADP max/min Ratio .............       3.30 oblat
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.77 Ratio
PLAT301_ALERT_3_C Main Residue  Disorder .........................      11.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          7
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl     ..  O3      ..       3.17 Ang.
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT779_ALERT_4_C Suspect or Irrelevant (Bond) Angle in CIF ......      43.20 Deg.
              F1   -C1   -F1'     1.555   1.555   1.555
PLAT779_ALERT_4_C Suspect or Irrelevant (Bond) Angle in CIF ......      38.40 Deg.
              F2'  -C1   -F2      1.555   1.555   1.555
PLAT779_ALERT_4_C Suspect or Irrelevant (Bond) Angle in CIF ......      32.40 Deg.
              F3   -C1   -F3'     1.555   1.555   1.555

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  10 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The title compound, (I), is generally recognized as an insect growth regulator that interferes with chitin synthesis in target pests causing death or abortive development (Wang et al., 1998). As part of our studies in this area, we report herein the crystal structure of the title compound (I).

In the molecule of (I) (Fig.1), the bond lengths and angles are within normal ranges (Allen et al., 1987). The intramolecular C—H···O and N—H···O hydrogen bonds are observed (Fig. 1, Table 1). Intermolecular N—H···O hydrogen bond generates a cyclic, centrosymmetric hydrogen bonded dimer (Table 1, Fig. 2).

Related literature top

For related literature, see: Allen et al. (1987); Wang et al. (1998); Qiu et al. (2004).

Experimental top

The title compound, (I), was prepared according to the literature method (Qiu et al., 1981). The crystals suitable for X-ray analysis were obtained by dissolving (I) (0.1 g) in acetonitrile (25 mL) and evaporating the solvent slowly at room temperature for about 6 d.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I) with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Intramolecular hydrogen bonds are shown by dased lines.
	Fig. 2. The crystal packing diagram with hydrogen bonds drawn as dashed lines.

1-(2-Chlorobenzoyl)-3-[4-(trifluoromethoxy)phenyl]urea top

Crystal data top

C₁₅H₁₀ClF₃N₂O₃	F(000) = 728
M_r = 358.70	D_x = 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 = 10–14°
b = 8.2870 (17) Å	µ = 0.30 mm⁻¹
c = 11.073 (2) Å	T = 298 K
β = 101.74 (3)°	Block, colourless
V = 1553.6 (6) Å³	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	1906 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.012
Graphite monochromator	θ_max = 25.2°, θ_min = 1.2°
ω/2θ scans	h = −20→20
Absorption correction: ψ scan (North et al., 1968)	k = 0→9
T_min = 0.917, T_max = 0.943	l = 0→13
2946 measured reflections	3 standard reflections every 200 reflections
2784 independent reflections	intensity decay: none

Refinement top

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)] = 0.079	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.186	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.06P)² + 3P] where P = (F_o² + 2F_c²)/3
2784 reflections	(Δ/σ)_max < 0.001
209 parameters	Δρ_max = 0.58 e Å⁻³
1 restraint	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₁₅H₁₀ClF₃N₂O₃	V = 1553.6 (6) Å³
M_r = 358.70	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.293 (4) Å	µ = 0.30 mm⁻¹
b = 8.2870 (17) Å	T = 298 K
c = 11.073 (2) Å	0.30 × 0.20 × 0.20 mm
β = 101.74 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1906 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.012
T_min = 0.917, T_max = 0.943	3 standard reflections every 200 reflections
2946 measured reflections	intensity decay: none
2784 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.079	1 restraint
wR(F²) = 0.186	H-atom parameters constrained
S = 1.01	Δρ_max = 0.58 e Å⁻³
2784 reflections	Δρ_min = −0.38 e Å⁻³
209 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₀ClF₃N₂O₃
M_r	358.70
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	17.293 (4), 8.2870 (17), 11.073 (2)
β (°)	101.74 (3)
V (Å³)	1553.6 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.917, 0.943
No. of measured, independent and observed [I > 2σ(I)] reflections	2946, 2784, 1906
R_int	0.012
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.079, 0.186, 1.01
No. of reflections	2784
No. of parameters	209
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.38

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).