1-(2-Chloro-3,5-difluoro­phen­yl)-3-(2,6-dichloro­benzo­yl)urea

Yan, S.-J.; Yan, Y.-Y.; Li, Y.-M.; Xie, M.-J.; Lin, J.

doi:10.1107/S1600536807023069

1-(2-Chloro-3,5-difluorophenyl)-3-(2,6-dichlorobenzoyl)urea

S.-J. Yan, Y.-Y. Yan, Y.-M. Li, M.-J. Xie and J. Lin

The 2-chloro-3,5-difluorophenyl ring of the title compound, C₁₄H₇Cl₃F₂N₂O₂, is almost coplanar with the urea group, whereas the 2,6-dichlorophenyl ring is twisted from the urea plane by 70.47 (11)°. An intramolecular N—H

O hydrogen bond stabilizes the molecular conformation and intermolecular N—H

O hydrogen bonds link the molecules into centrosymmetric dimers.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807023069/bt2353sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807023069/bt2353Isup2.hkl Contains datablock I

CCDC reference: 651469

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.006 Å
R factor = 0.049
wR factor = 0.239
Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.92
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          6

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.917
            Tmax scaled      0.917 Tmin scaled      0.760
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

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

Comment top

Derivatives of benzoylphenylureas are insect growth regulators. The title compound (Fig. 1), possesses high bioactivity (Yan et al., 2003).

The 2-chloro-3,5-difluorophenyl ring is almost coplanar with the urea moiety, whereas the 2,6-dichlorophenyl ring is twisted from the urea plane by 70.47 (11)°. An intramolecular N—H···O hydrogen bond stabilized the molecular conformation and intermolecular N—H···O hydrogen bonds link the molecules to centrosymmetric dimers.

Related literature top

For related literature, see: Yan et al. (2003); Lin et al. (2003).

Experimental top

(I) was prepared according to the procedure of (Lin et al., 2003). The desire product was recrystallized from acetone/chloroform=4/1 (m.p. 505 K).

Structure description top

Derivatives of benzoylphenylureas are insect growth regulators. The title compound (Fig. 1), possesses high bioactivity (Yan et al., 2003).

For related literature, see: Yan et al. (2003); Lin et al. (2003).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

Figures top

Fig. 1. View of the title compound showing 30% displacement ellipsoids (arbitrary spheres for the H atoms).

1-(2-Chloro-3,5-difluorophenyl)-3-(2,6-dichlorobenzoyl)urea top

Crystal data top

C₁₄H₇Cl₃F₂N₂O₂	D_x = 1.628 Mg m⁻³
M_r = 379.57	Melting point: 505 K
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.7027 (13) Å	Cell parameters from 3462 reflections
b = 9.5225 (11) Å	θ = 2.6–27.3°
c = 14.7144 (16) Å	µ = 0.62 mm⁻¹
β = 109.160 (1)°	T = 293 K
V = 1548.9 (3) Å³	Block, colourless
Z = 4	0.39 × 0.26 × 0.14 mm
F(000) = 760

Data collection top

Bruker SMART CCD area-detector diffractometer	3462 independent reflections
Radiation source: fine-focus sealed tube	2307 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
phi and ω scans	θ_max = 27.3°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −11→15
T_min = 0.829, T_max = 1.000	k = −12→10
9520 measured reflections	l = −18→18

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.239	H-atom parameters constrained
S = 0.87	w = 1/[σ²(F_o²) + (0.2P)²] where P = (F_o² + 2F_c²)/3
3462 reflections	(Δ/σ)_max < 0.001
208 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

C₁₄H₇Cl₃F₂N₂O₂	V = 1548.9 (3) Å³
M_r = 379.57	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.7027 (13) Å	µ = 0.62 mm⁻¹
b = 9.5225 (11) Å	T = 293 K
c = 14.7144 (16) Å	0.39 × 0.26 × 0.14 mm
β = 109.160 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3462 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	2307 reflections with I > 2σ(I)
T_min = 0.829, T_max = 1.000	R_int = 0.020
9520 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.239	H-atom parameters constrained
S = 0.87	Δρ_max = 0.39 e Å⁻³
3462 reflections	Δρ_min = −0.49 e Å⁻³
208 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
Cl1	0.74290 (10)	0.51164 (14)	−0.12803 (7)	0.0906 (4)
Cl2	0.92514 (10)	0.44553 (12)	0.25737 (7)	0.0865 (4)
F2	0.2694 (2)	1.0356 (3)	0.1389 (3)	0.1178 (11)
F1	0.6237 (3)	1.2972 (2)	0.18137 (19)	0.0967 (8)
Cl3	0.76294 (8)	1.07123 (10)	0.13581 (7)	0.0759 (4)
O1	0.83312 (19)	0.7084 (2)	0.10878 (19)	0.0686 (7)
O2	0.46593 (18)	0.6550 (2)	0.04196 (19)	0.0684 (7)
N1	0.6563 (2)	0.5864 (3)	0.05747 (18)	0.0515 (6)
H1A	0.6267	0.5060	0.0351	0.062*
N2	0.6191 (2)	0.8124 (2)	0.10223 (17)	0.0488 (6)
H2A	0.6960	0.8224	0.1162	0.059*
C1	0.8433 (2)	0.4721 (3)	0.0628 (2)	0.0502 (7)
C2	0.8377 (3)	0.4269 (3)	−0.0279 (3)	0.0609 (8)
C3	0.9089 (4)	0.3162 (4)	−0.0398 (4)	0.0827 (12)
H3A	0.9050	0.2874	−0.1012	0.099*
C4	0.9847 (4)	0.2500 (4)	0.0396 (5)	0.0928 (14)
H4A	1.0328	0.1763	0.0318	0.111*
C5	0.9909 (3)	0.2902 (4)	0.1303 (4)	0.0799 (11)
H5A	1.0426	0.2440	0.1836	0.096*
C6	0.9206 (3)	0.3992 (3)	0.1421 (3)	0.0589 (8)
C7	0.7774 (2)	0.6002 (3)	0.0787 (2)	0.0476 (6)
C8	0.5729 (2)	0.6860 (3)	0.0671 (2)	0.0475 (6)
C9	0.4372 (3)	0.9227 (4)	0.1192 (2)	0.0605 (8)
H9A	0.3939	0.8390	0.1060	0.073*
C10	0.3858 (4)	1.0433 (4)	0.1399 (3)	0.0754 (10)
C11	0.4471 (4)	1.1691 (4)	0.1618 (3)	0.0798 (11)
H11A	0.4107	1.2484	0.1770	0.096*
C12	0.5611 (4)	1.1729 (3)	0.1603 (3)	0.0690 (9)
C13	0.6186 (3)	1.0571 (3)	0.1376 (2)	0.0532 (7)
C14	0.5551 (3)	0.9293 (3)	0.11844 (19)	0.0466 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0914 (8)	0.1152 (10)	0.0616 (6)	0.0079 (6)	0.0202 (5)	−0.0108 (5)
Cl2	0.0892 (8)	0.0866 (7)	0.0716 (6)	−0.0075 (5)	0.0102 (5)	0.0057 (5)
F2	0.0839 (18)	0.107 (2)	0.188 (3)	0.0253 (15)	0.079 (2)	0.0004 (19)
F1	0.130 (2)	0.0489 (11)	0.1098 (18)	−0.0114 (12)	0.0373 (15)	−0.0197 (12)
Cl3	0.0663 (6)	0.0682 (6)	0.0937 (7)	−0.0246 (4)	0.0267 (5)	−0.0193 (4)
O1	0.0412 (11)	0.0557 (13)	0.1073 (19)	−0.0123 (9)	0.0222 (11)	−0.0245 (12)
O2	0.0379 (11)	0.0596 (13)	0.1061 (18)	−0.0084 (9)	0.0214 (11)	−0.0244 (12)
N1	0.0386 (12)	0.0436 (12)	0.0706 (16)	−0.0066 (9)	0.0156 (11)	−0.0155 (11)
N2	0.0382 (11)	0.0468 (13)	0.0622 (14)	−0.0040 (9)	0.0175 (10)	−0.0090 (10)
C1	0.0392 (14)	0.0438 (14)	0.0686 (19)	−0.0052 (11)	0.0189 (13)	−0.0071 (13)
C2	0.0534 (17)	0.0535 (18)	0.080 (2)	−0.0052 (13)	0.0272 (16)	−0.0121 (15)
C3	0.078 (3)	0.068 (2)	0.119 (3)	−0.006 (2)	0.056 (3)	−0.027 (2)
C4	0.071 (2)	0.055 (2)	0.165 (5)	0.0121 (18)	0.057 (3)	−0.005 (3)
C5	0.058 (2)	0.057 (2)	0.124 (4)	0.0057 (16)	0.028 (2)	0.012 (2)
C6	0.0446 (15)	0.0485 (17)	0.081 (2)	−0.0038 (12)	0.0179 (15)	0.0049 (15)
C7	0.0372 (13)	0.0470 (15)	0.0580 (16)	−0.0053 (10)	0.0150 (11)	−0.0083 (12)
C8	0.0356 (13)	0.0467 (14)	0.0577 (15)	−0.0040 (10)	0.0118 (11)	−0.0072 (12)
C9	0.0570 (18)	0.0577 (18)	0.071 (2)	0.0066 (13)	0.0272 (15)	0.0031 (15)
C10	0.073 (2)	0.077 (2)	0.088 (3)	0.0231 (19)	0.042 (2)	0.008 (2)
C11	0.100 (3)	0.058 (2)	0.085 (2)	0.024 (2)	0.036 (2)	−0.0022 (18)
C12	0.093 (3)	0.0463 (17)	0.065 (2)	0.0044 (16)	0.0221 (18)	−0.0032 (14)
C13	0.0613 (18)	0.0493 (16)	0.0472 (15)	−0.0033 (12)	0.0154 (13)	−0.0049 (12)
C14	0.0512 (15)	0.0461 (14)	0.0422 (13)	0.0006 (11)	0.0150 (11)	−0.0004 (11)

Geometric parameters (Å, º) top

Cl1—C2	1.726 (4)	C2—C3	1.390 (5)
Cl2—C6	1.737 (4)	C3—C4	1.368 (7)
F2—C10	1.359 (4)	C3—H3A	0.9300
F1—C12	1.373 (4)	C4—C5	1.366 (7)
Cl3—C13	1.704 (3)	C4—H4A	0.9300
O1—C7	1.222 (3)	C5—C6	1.371 (5)
O2—C8	1.219 (3)	C5—H5A	0.9300
N1—C7	1.354 (3)	C9—C10	1.377 (5)
N1—C8	1.401 (4)	C9—C14	1.385 (5)
N1—H1A	0.8600	C9—H9A	0.9300
N2—C8	1.351 (4)	C10—C11	1.378 (6)
N2—C14	1.405 (4)	C11—C12	1.343 (6)
N2—H2A	0.8600	C11—H11A	0.9300
C1—C2	1.384 (5)	C12—C13	1.389 (5)
C1—C6	1.403 (4)	C13—C14	1.404 (4)
C1—C7	1.502 (4)

C7—N1—C8	128.5 (2)	O1—C7—N1	124.0 (3)
C7—N1—H1A	115.8	O1—C7—C1	120.0 (2)
C8—N1—H1A	115.8	N1—C7—C1	116.0 (2)
C8—N2—C14	127.1 (2)	O2—C8—N2	125.0 (3)
C8—N2—H2A	116.5	O2—C8—N1	119.0 (2)
C14—N2—H2A	116.5	N2—C8—N1	115.9 (2)
C2—C1—C6	117.5 (3)	C10—C9—C14	118.2 (3)
C2—C1—C7	122.6 (3)	C10—C9—H9A	120.9
C6—C1—C7	119.8 (3)	C14—C9—H9A	120.9
C1—C2—C3	121.1 (4)	F2—C10—C9	117.5 (4)
C1—C2—Cl1	119.5 (2)	F2—C10—C11	119.5 (3)
C3—C2—Cl1	119.4 (3)	C9—C10—C11	123.0 (4)
C4—C3—C2	119.3 (4)	C12—C11—C10	117.6 (3)
C4—C3—H3A	120.4	C12—C11—H11A	121.2
C2—C3—H3A	120.4	C10—C11—H11A	121.2
C5—C4—C3	121.2 (3)	C11—C12—F1	118.6 (3)
C5—C4—H4A	119.4	C11—C12—C13	123.0 (3)
C3—C4—H4A	119.4	F1—C12—C13	118.4 (3)
C4—C5—C6	119.6 (4)	C12—C13—C14	118.1 (3)
C4—C5—H5A	120.2	C12—C13—Cl3	120.1 (3)
C6—C5—H5A	120.2	C14—C13—Cl3	121.8 (2)
C5—C6—C1	121.3 (4)	C9—C14—C13	120.0 (3)
C5—C6—Cl2	119.3 (3)	C9—C14—N2	123.5 (3)
C1—C6—Cl2	119.4 (2)	C13—C14—N2	116.4 (3)

C6—C1—C2—C3	−2.0 (5)	C14—N2—C8—N1	179.8 (3)
C7—C1—C2—C3	173.7 (3)	C7—N1—C8—O2	178.3 (3)
C6—C1—C2—Cl1	179.3 (2)	C7—N1—C8—N2	0.0 (4)
C7—C1—C2—Cl1	−5.0 (4)	C14—C9—C10—F2	179.0 (3)
C1—C2—C3—C4	0.7 (5)	C14—C9—C10—C11	−1.3 (6)
Cl1—C2—C3—C4	179.4 (3)	F2—C10—C11—C12	−178.8 (3)
C2—C3—C4—C5	0.5 (6)	C9—C10—C11—C12	1.5 (6)
C3—C4—C5—C6	−0.3 (6)	C10—C11—C12—F1	179.7 (4)
C4—C5—C6—C1	−1.0 (5)	C10—C11—C12—C13	0.2 (6)
C4—C5—C6—Cl2	177.7 (3)	C11—C12—C13—C14	−2.1 (5)
C2—C1—C6—C5	2.2 (4)	F1—C12—C13—C14	178.5 (3)
C7—C1—C6—C5	−173.7 (3)	C11—C12—C13—Cl3	179.2 (3)
C2—C1—C6—Cl2	−176.6 (2)	F1—C12—C13—Cl3	−0.3 (4)
C7—C1—C6—Cl2	7.5 (4)	C10—C9—C14—C13	−0.6 (5)
C8—N1—C7—O1	−1.9 (5)	C10—C9—C14—N2	177.3 (3)
C8—N1—C7—C1	178.4 (3)	C12—C13—C14—C9	2.3 (4)
C2—C1—C7—O1	−105.4 (4)	Cl3—C13—C14—C9	−179.0 (2)
C6—C1—C7—O1	70.3 (4)	C12—C13—C14—N2	−175.8 (3)
C2—C1—C7—N1	74.4 (4)	Cl3—C13—C14—N2	2.9 (4)
C6—C1—C7—N1	−110.0 (3)	C8—N2—C14—C9	14.0 (5)
C14—N2—C8—O2	1.6 (5)	C8—N2—C14—C13	−168.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Cl3	0.86	2.48	2.934 (2)	114
N2—H2A···O1	0.86	1.97	2.666 (3)	137
N1—H1A···O2ⁱ	0.86	2.00	2.846 (3)	167

Symmetry code: (i) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₄H₇Cl₃F₂N₂O₂
M_r	379.57
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	11.7027 (13), 9.5225 (11), 14.7144 (16)
β (°)	109.160 (1)
V (Å³)	1548.9 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.62
Crystal size (mm)	0.39 × 0.26 × 0.14

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.829, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	9520, 3462, 2307
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.645

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.239, 0.87
No. of reflections	3462
No. of parameters	208
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.49

Computer programs: SMART (Bruker, 1998), SMART, SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998), SHELXTL.