N-Benzoyl-N′-phenyl­urea

Okuniewski, A.; Chojnacki, J.; Becker, B.

doi:10.1107/S1600536810001807

organic compounds

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ISSN: 2056-9890

Volume 66| Part 2| February 2010| Page o414

https://doi.org/10.1107/S1600536810001807

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N-Benzoyl-N′-phenylurea

Andrzej Okuniewski,^a Jaroslaw Chojnacki ^a and Barbara Becker ^a ^*

^aDepartment of Inorganic Chemistry, Gdansk University of Technology, Narutowicza 11/12, 80-233 Gdańsk, Poland
^*Correspondence e-mail: barbara.becker@pg.gda.pl

(Received 8 January 2010; accepted 14 January 2010; online 20 January 2010)

In the title compound, C₁₄H₁₂N₂O₂, the molecular conformation is determined by a strong intramolecular N—H⋯O=C hydrogen bond. In the crystal, pairs of molecules are connected by intermolecular N—H⋯O=C hydrogen bonds, forming centrosymmetric dimers. No specific interactions between dimers could be found.

Related literature

For related structures, see: Bart et al. (1989 ); Zhong et al. (1998 ); Moon et al. (2002 ), Yamin & Mardi (2003 ); Chen et al. (2004 ); Su (2005 ); Yan et al. (2007 , 2008 ); Liu et al. (2008 , 2008a ,b ). For graph-set notation, see: Etter (1990 ). The title compound was obtained as a byproduct during the synthesis of a copper(I) complex with N-benzoyl-N′-phenylthiourea prepared according to Frank & Smith (1948 ).

Experimental

Crystal data

C₁₄H₁₂N₂O₂
M_r = 240.26
Monoclinic, P 2₁ /c
a = 15.5641 (8) Å
b = 4.6564 (3) Å
c = 21.1029 (15) Å
β = 128.716 (4)°
V = 1193.31 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 150 K
0.54 × 0.10 × 0.09 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire2 (large Be window) detector
Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); analytical numeric absorption correction using a multi-faceted crystal model based on expressions derived by Clark & Reid (1995 )] T_min = 0.971, T_max = 0.993
4425 measured reflections
2221 independent reflections
1575 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.098
S = 0.94
2221 reflections
211 parameters
Only H-atom coordinates refined
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.93 (2)	1.85 (2)	2.634 (2)	140 (1)
N2—H2⋯O1ⁱ	0.93 (2)	1.97 (2)	2.882 (1)	169 (1)
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO 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 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810001807/im2175sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810001807/im2175Isup2.hkl

checkCIF report

Comment top

N-Benzoyl-N'-phenylurea halogeno derivatives are used as pesticides. For instance 1-(3,5-dichloro-2,4-difluorophenyl)-3-(2,6-difluorobenzoyl)urea was found to act as chitin synthesis inhibitor (Zhong et al.,1998).

N-benzoyl-N'-phenylurea molecules adopt a conformation that allows formation of N—H···O═C intramolecular hydrogen bonds, denoted as R(6) in graph set notation (Etter, 1990). This conformation is commonly noted among all N'-monosubstituted or N'-unsubstituted N-benzoylureas and N-benzoylthioureas (see: related structures). Additional N—H···O═C intermolecular R²₂(8) hydrogen bonds bind two urea derivative molecules to form a centrosymmetric dimer (Fig. 1), which is also common. Only one known structure does not exhibit such a motif (Moon et al., 2002).

No π-π stacking interactions can be found in this structure (closest ring centroids distance is about 5.60 Å with the dihedral angle between the rings α about 80°).

The dihedral angle N1—C1—N2—C2 describing the twist of two amide subunits of urea derivatives is equal to 3.0 (2)°. This value is in the range known from other studies: from 0.07° (Yan et al., 2007) to 7.45° (Su, 2005).

Related literature top

For related structures, see: Bart et al. (1989); Zhong et al. (1998); Moon et al. (2002), Yamin & Mardi (2003); Chen et al. (2004); Su (2005); Yan et al. (2007, 2008); Liu et al. (2008, 2008a,b). For graph-set notation, see: Etter (1990). The title compound was obtained as a byproduct during the synthesis of a copper(I) complex with N-benzoyl-N'-phenylthiourea prepared according to Frank & Smith (1948).

Experimental top

N-benzoyl-N'-phenylurea was obtained as a byproduct during the synthesis of a copper(I) complex with N-Benzoyl-N'-phenylthiourea prepared according to Frank & Smith (1948). Obviously the ligand underwent basic hydrolysis with CH₃ONa in acetone. Colourless single crystals suitable for X-ray diffraction analysis were isolated from the reaction mixture after it was kept at room temperature for a few days. From 5.12 g (0.02 mol) of thiourea derivative 0.87 g of N-benzoyl-N'-phenylurea was obtained. Yield: 18%.

Structure description top

No π-π stacking interactions can be found in this structure (closest ring centroids distance is about 5.60 Å with the dihedral angle between the rings α about 80°).

For related structures, see: Bart et al. (1989); Zhong et al. (1998); Moon et al. (2002), Yamin & Mardi (2003); Chen et al. (2004); Su (2005); Yan et al. (2007, 2008); Liu et al. (2008, 2008a,b). For graph-set notation, see: Etter (1990). The title compound was obtained as a byproduct during the synthesis of a copper(I) complex with N-benzoyl-N'-phenylthiourea prepared according to Frank & Smith (1948).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); 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) and PLATON (Spek, 2009).

Figures top

Fig. 1. Structure of centrosymmetric N-benzoyl-N'-phenylurea dimer. Ellipsoids are drawn at 50% probability level. Symmetry code: (i) –x+1, –y+1, –z.

N-Benzoyl-N'-phenylurea top

Crystal data top

C₁₄H₁₂N₂O₂	F(000) = 504
M_r = 240.26	D_x = 1.337 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 482(2) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 15.5641 (8) Å	Cell parameters from 2481 reflections
b = 4.6564 (3) Å	θ = 2.5–28.4°
c = 21.1029 (15) Å	µ = 0.09 mm⁻¹
β = 128.716 (4)°	T = 150 K
V = 1193.31 (15) Å³	Needle, colourless
Z = 4	0.54 × 0.10 × 0.09 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire2 (large Be window) detector	2221 independent reflections
Radiation source: Mo Kα radiation	1575 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
Detector resolution: 8.1883 pixels mm^-1	θ_max = 25.5°, θ_min = 2.5°
ω scans	h = −18→9
Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2009); analytical numeric absorption correction using a multi-faceted crystal model based on expressions derived by Clark & Reid (1995)]	k = −3→5
T_min = 0.971, T_max = 0.993	l = −21→25
4425 measured reflections

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)] = 0.039	Hydrogen site location: difference Fourier map
wR(F²) = 0.098	Only H-atom coordinates refined
S = 0.94	w = 1/[σ²(F_o²) + (0.0656P)²] where P = (F_o² + 2F_c²)/3
2221 reflections	(Δ/σ)_max < 0.001
211 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₁₄H₁₂N₂O₂	V = 1193.31 (15) Å³
M_r = 240.26	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.5641 (8) Å	µ = 0.09 mm⁻¹
b = 4.6564 (3) Å	T = 150 K
c = 21.1029 (15) Å	0.54 × 0.10 × 0.09 mm
β = 128.716 (4)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire2 (large Be window) detector	2221 independent reflections
Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2009); analytical numeric absorption correction using a multi-faceted crystal model based on expressions derived by Clark & Reid (1995)]	1575 reflections with I > 2σ(I)
T_min = 0.971, T_max = 0.993	R_int = 0.022
4425 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.098	Only H-atom coordinates refined
S = 0.94	Δρ_max = 0.22 e Å⁻³
2221 reflections	Δρ_min = −0.14 e Å⁻³
211 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
O1	0.58625 (7)	0.6582 (2)	−0.00745 (6)	0.0384 (3)
O2	0.82393 (7)	0.2951 (2)	0.21526 (6)	0.0396 (3)
N1	0.77093 (9)	0.6517 (3)	0.09887 (7)	0.0295 (3)
N2	0.64890 (9)	0.3566 (3)	0.09771 (7)	0.0284 (3)
C1	0.66640 (10)	0.5660 (3)	0.05886 (8)	0.0274 (3)
C2	0.72519 (10)	0.2381 (3)	0.17319 (8)	0.0282 (3)
C11	0.81196 (11)	0.8530 (3)	0.07373 (9)	0.0297 (4)
C12	0.74750 (12)	0.9966 (3)	−0.00011 (9)	0.0330 (4)
C13	0.79673 (13)	1.1897 (4)	−0.01876 (10)	0.0393 (4)
C14	0.90876 (14)	1.2390 (4)	0.03479 (11)	0.0469 (5)
C15	0.97228 (13)	1.0949 (4)	0.10784 (12)	0.0516 (5)
C16	0.92476 (12)	0.9038 (4)	0.12780 (11)	0.0411 (4)
C21	0.68355 (10)	0.0351 (3)	0.20329 (8)	0.0275 (3)
C22	0.75435 (12)	−0.0253 (3)	0.28626 (9)	0.0336 (4)
C23	0.72257 (13)	−0.2128 (4)	0.31894 (10)	0.0389 (4)
C24	0.61969 (13)	−0.3423 (4)	0.26921 (10)	0.0390 (4)
C25	0.54898 (12)	−0.2851 (3)	0.18661 (10)	0.0368 (4)
C26	0.58046 (11)	−0.0960 (3)	0.15362 (9)	0.0316 (4)
H1	0.8205 (12)	0.559 (3)	0.1480 (10)	0.039 (4)*
H13	0.7502 (12)	1.291 (4)	−0.0711 (10)	0.041 (4)*
H12	0.6663 (12)	0.961 (3)	−0.0395 (8)	0.032 (4)*
H2	0.5745 (13)	0.328 (3)	0.0717 (9)	0.041 (4)*
H23	0.7751 (12)	−0.257 (3)	0.3782 (10)	0.040 (4)*
H26	0.5289 (12)	−0.059 (3)	0.0951 (9)	0.032 (4)*
H22	0.8256 (13)	0.077 (4)	0.3210 (9)	0.044 (4)*
H25	0.4762 (13)	−0.375 (3)	0.1504 (9)	0.043 (4)*
H24	0.5963 (12)	−0.477 (4)	0.2916 (9)	0.043 (4)*
H14	0.9397 (13)	1.385 (4)	0.0187 (10)	0.056 (5)*
H15	1.0520 (15)	1.117 (4)	0.1465 (10)	0.060 (5)*
H16	0.9654 (14)	0.800 (4)	0.1778 (11)	0.055 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0223 (5)	0.0518 (7)	0.0288 (6)	−0.0014 (4)	0.0100 (5)	0.0106 (5)
O2	0.0231 (5)	0.0527 (7)	0.0304 (6)	−0.0018 (5)	0.0107 (5)	0.0068 (5)
N1	0.0205 (6)	0.0363 (7)	0.0235 (6)	−0.0025 (5)	0.0097 (5)	0.0026 (6)
N2	0.0199 (6)	0.0351 (7)	0.0239 (6)	−0.0017 (5)	0.0106 (5)	0.0007 (6)
C1	0.0234 (7)	0.0333 (8)	0.0226 (7)	−0.0020 (6)	0.0130 (6)	−0.0018 (7)
C2	0.0237 (7)	0.0320 (8)	0.0243 (7)	0.0018 (6)	0.0128 (6)	−0.0015 (7)
C11	0.0275 (7)	0.0316 (8)	0.0297 (8)	−0.0041 (6)	0.0178 (6)	−0.0048 (7)
C12	0.0308 (8)	0.0373 (9)	0.0289 (8)	−0.0040 (6)	0.0178 (7)	−0.0030 (7)
C13	0.0443 (9)	0.0417 (10)	0.0360 (9)	−0.0046 (7)	0.0270 (8)	−0.0006 (8)
C14	0.0473 (10)	0.0458 (11)	0.0562 (11)	−0.0118 (8)	0.0366 (9)	−0.0009 (9)
C15	0.0303 (9)	0.0560 (12)	0.0579 (12)	−0.0089 (8)	0.0223 (9)	0.0049 (10)
C16	0.0273 (8)	0.0438 (10)	0.0413 (10)	−0.0041 (7)	0.0162 (7)	0.0051 (9)
C21	0.0279 (7)	0.0267 (8)	0.0276 (7)	0.0058 (6)	0.0173 (6)	0.0011 (7)
C22	0.0333 (8)	0.0339 (9)	0.0286 (8)	0.0037 (6)	0.0169 (7)	0.0011 (7)
C23	0.0441 (9)	0.0422 (10)	0.0296 (8)	0.0067 (7)	0.0227 (7)	0.0047 (8)
C24	0.0471 (9)	0.0367 (9)	0.0444 (9)	0.0052 (7)	0.0340 (8)	0.0080 (8)
C25	0.0357 (8)	0.0356 (9)	0.0425 (9)	0.0002 (7)	0.0261 (8)	0.0015 (8)
C26	0.0282 (7)	0.0355 (9)	0.0286 (8)	0.0033 (6)	0.0165 (7)	0.0026 (7)

Geometric parameters (Å, º) top

O1—C1	1.2308 (16)	C14—H14	1.007 (19)
O2—C2	1.2304 (15)	C15—C16	1.381 (2)
N1—C1	1.3419 (16)	C15—H15	0.975 (18)
N1—C11	1.4114 (18)	C16—H16	0.956 (19)
N1—H1	0.926 (16)	C21—C26	1.394 (2)
N2—C2	1.3731 (18)	C21—C22	1.3950 (19)
N2—C1	1.4058 (18)	C22—C23	1.382 (2)
N2—H2	0.930 (15)	C22—H22	0.988 (16)
C2—C21	1.494 (2)	C23—C24	1.388 (2)
C11—C12	1.388 (2)	C23—H23	0.998 (16)
C11—C16	1.3907 (19)	C24—C25	1.386 (2)
C12—C13	1.388 (2)	C24—H24	0.983 (17)
C12—H12	1.001 (14)	C25—C26	1.388 (2)
C13—C14	1.380 (2)	C25—H25	0.980 (16)
C13—H13	0.984 (17)	C26—H26	0.979 (15)
C14—C15	1.378 (3)

C1—N1—C11	128.07 (12)	C14—C15—C16	120.59 (15)
C1—N1—H1	113.5 (9)	C14—C15—H15	122.2 (10)
C11—N1—H1	118.4 (9)	C16—C15—H15	117.2 (11)
C2—N2—C1	127.79 (11)	C15—C16—C11	120.10 (16)
C2—N2—H2	118.7 (9)	C15—C16—H16	123.5 (10)
C1—N2—H2	112.3 (10)	C11—C16—H16	116.4 (10)
O1—C1—N1	125.41 (14)	C26—C21—C22	119.31 (14)
O1—C1—N2	118.47 (11)	C26—C21—C2	123.99 (13)
N1—C1—N2	116.12 (12)	C22—C21—C2	116.69 (13)
O2—C2—N2	122.27 (13)	C23—C22—C21	120.37 (14)
O2—C2—C21	120.53 (12)	C23—C22—H22	121.3 (9)
N2—C2—C21	117.20 (12)	C21—C22—H22	118.3 (9)
C12—C11—C16	119.63 (14)	C22—C23—C24	120.06 (15)
C12—C11—N1	124.25 (12)	C22—C23—H23	119.3 (9)
C16—C11—N1	116.12 (13)	C24—C23—H23	120.7 (9)
C11—C12—C13	119.38 (14)	C25—C24—C23	120.03 (15)
C11—C12—H12	120.2 (8)	C25—C24—H24	119.1 (9)
C13—C12—H12	120.4 (8)	C23—C24—H24	120.9 (9)
C14—C13—C12	120.96 (16)	C24—C25—C26	120.07 (15)
C14—C13—H13	120.3 (9)	C24—C25—H25	121.3 (9)
C12—C13—H13	118.7 (9)	C26—C25—H25	118.6 (9)
C15—C14—C13	119.33 (16)	C25—C26—C21	120.16 (14)
C15—C14—H14	123.1 (10)	C25—C26—H26	118.5 (9)
C13—C14—H14	117.5 (10)	C21—C26—H26	121.4 (9)

N1—C1—N2—C2	3.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.93 (2)	1.85 (2)	2.634 (2)	140 (1)
N2—H2···O1ⁱ	0.93 (2)	1.97 (2)	2.882 (1)	169 (1)

Symmetry code: (i) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₂N₂O₂
M_r	240.26
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	15.5641 (8), 4.6564 (3), 21.1029 (15)
β (°)	128.716 (4)
V (Å³)	1193.31 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.54 × 0.10 × 0.09

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Sapphire2 (large Be window) detector
Absorption correction	Analytical [CrysAlis PRO (Oxford Diffraction, 2009); analytical numeric absorption correction using a multi-faceted crystal model based on expressions derived by Clark & Reid (1995)]
T_min, T_max	0.971, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	4425, 2221, 1575
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.098, 0.94
No. of reflections	2221
No. of parameters	211
H-atom treatment	Only H-atom coordinates refined
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.14

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.93 (2)	1.85 (2)	2.634 (2)	140 (1)
N2—H2···O1ⁱ	0.93 (2)	1.97 (2)	2.882 (1)	169 (1)

Symmetry code: (i) −x+1, −y+1, −z.

References

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