Crystal structure of pencycuron.

In the title compound [systematic name: 1-(4-chloro-benz-yl)-1-cyclo-pentyl-3-phenyl-urea], C19H21ClN2O, which is a urea fungicide, the cyclo-pentyl ring adopts an envelope conformation, with one of the methyl-ene C atoms adjacent to the C atom bonding to the N atom as the flap. The dihedral angles between the mean planes of the central cyclo-pentyl ring (all atoms) and the chloro-benzyl and phenyl rings are 77.96 (6) and 57.77 (7)°, respectively. In the crystal, N-H⋯O hydrogen bonds link adjacent mol-ecules, forming C(4) chains propagating along the b-axis direction. The chains are linked by weak π-π inter-actions between the chloro-benzene rings [centroid-centroid separation = 3.9942 (9) Å], resulting in two-dimensional networks extending parellel to the (110) plane.

Related literature

For information on the fungicidal properties of the title compound, see: Pal et al. (2005 ▸). For a related crystal structure, see: Bjerglund et al. (2012 ▸).

Experimental

Crystal data

C19H21ClN2O

M = 328.83

Orthorhombic,

a = 12.1585 (5) Å

b = 8.6721 (4) Å

c = 32.6152 (12) Å

V = 3438.9 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.23 mm−1

T = 173 K

0.50 × 0.11 × 0.09 mm

Data collection

Bruker APEX-II CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▸) T min = 0.894, T max = 0.980

27037 measured reflections

3374 independent reflections

2698 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.095

S = 1.04

3374 reflections

212 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2009 ▸); cell refinement: SAINT (Bruker, 2009 ▸); data reduction: SAIn class="Chemical">NT; program(s) used to solve structure: SHELXS97 (Sheldrick 2008 ▸); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015 ▸); molecular graphics: DIAMOND (Brandenburg, 2010 ▸); software used to prepare material for publication: SHELXTL (Sheldrick 2008 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015012414/hb7456sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015012414/hb7456Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015012414/hb7456Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015012414/hb7456fig1.tif

The asymmetric unit of the title compound with displacement ellipsoids drawn at the 50% probability level.

Click here for additional data file.

a . DOI: 10.1107/S2056989015012414/hb7456fig2.tif

Crystal packing viewed along the a axis. The inter­molecular N—H⋯O n class="Chemical">hydrogen bonds and weak π–π inter­actions are shown as dashed lines.

CCDC reference: 1409194

Additional supporting information: crystallographic information; 3D view; checkCIF report

C19H21ClN2O	Dx = 1.270 Mg m−3
Mr = 328.83	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 6227 reflections
a = 12.1585 (5) Å	θ = 2.5–27.3°
b = 8.6721 (4) Å	µ = 0.23 mm−1
c = 32.6152 (12) Å	T = 173 K
V = 3438.9 (2) Å3	Needle, colourless
Z = 8	0.50 × 0.11 × 0.09 mm
F(000) = 1392

Bruker APEX-II CCD diffractometer	2698 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.039
Absorption correction: multi-scan (SADABS; Bruker, 2009)	θmax = 26.0°, θmin = 2.1°
Tmin = 0.894, Tmax = 0.980	h = −14→14
27037 measured reflections	k = −6→10
3374 independent reflections	l = −40→40

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.095	w = 1/[σ2(Fo2) + (0.0384P)2 + 1.2518P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
3374 reflections	Δρmax = 0.17 e Å−3
212 parameters	Δρmin = −0.24 e Å−3

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.

	x	y	z	Uiso*/Ueq
Cl1	0.23590 (4)	−0.16966 (8)	−0.05434 (2)	0.06131 (19)
O1	0.15878 (8)	−0.14846 (11)	0.15909 (3)	0.0287 (2)
N1	0.08966 (10)	0.07872 (15)	0.13656 (4)	0.0278 (3)
N2	0.23017 (10)	0.07453 (16)	0.18515 (4)	0.0288 (3)
H2N	0.2489 (14)	0.162 (2)	0.1777 (5)	0.039 (5)*
C1	0.17668 (14)	−0.1232 (2)	−0.00710 (5)	0.0384 (4)
C2	0.22919 (13)	−0.0213 (2)	0.01841 (5)	0.0397 (4)
H2	0.2975	0.0233	0.0106	0.048*
C3	0.18127 (12)	0.0160 (2)	0.05576 (5)	0.0355 (4)
H3	0.2173	0.0863	0.0736	0.043*
C4	0.08150 (12)	−0.04807 (17)	0.06739 (4)	0.0277 (3)
C5	0.03091 (13)	−0.15110 (19)	0.04097 (5)	0.0327 (4)
H5	−0.0373	−0.1962	0.0486	0.039*
C6	0.07769 (14)	−0.1895 (2)	0.00376 (5)	0.0390 (4)
H6	0.0423	−0.2604	−0.0141	0.047*
C7	0.02356 (12)	−0.00774 (19)	0.10708 (4)	0.0298 (3)
H7A	−0.0428	0.0535	0.1005	0.036*
H7B	−0.0012	−0.1045	0.1203	0.036*
C8	0.06470 (12)	0.24352 (18)	0.14250 (5)	0.0315 (4)
H8	0.1190	0.2854	0.1627	0.038*
C9	0.07296 (15)	0.3403 (2)	0.10377 (5)	0.0436 (4)
H9A	0.0381	0.2873	0.0802	0.052*
H9B	0.1506	0.3629	0.0969	0.052*
C10	0.01105 (17)	0.4869 (2)	0.11481 (6)	0.0532 (5)
H10A	−0.0149	0.5406	0.0898	0.064*
H10B	0.0584	0.5579	0.1307	0.064*
C11	−0.08580 (17)	0.4315 (2)	0.14061 (7)	0.0565 (5)
H11A	−0.1520	0.4182	0.1233	0.068*
H11B	−0.1027	0.5070	0.1625	0.068*
C12	−0.05145 (14)	0.2774 (2)	0.15928 (6)	0.0421 (4)
H12A	−0.1033	0.1949	0.1511	0.050*
H12B	−0.0502	0.2841	0.1896	0.050*
C13	0.15966 (11)	−0.00577 (17)	0.16037 (4)	0.0249 (3)
C14	0.29239 (11)	0.00718 (17)	0.21711 (4)	0.0255 (3)
C15	0.39770 (12)	0.06323 (18)	0.22439 (5)	0.0300 (3)
H15	0.4283	0.1387	0.2066	0.036*
C16	0.45819 (13)	0.0096 (2)	0.25737 (5)	0.0357 (4)
H16	0.5295	0.0500	0.2625	0.043*
C17	0.41528 (14)	−0.1025 (2)	0.28280 (5)	0.0381 (4)
H17	0.4569	−0.1396	0.3054	0.046*
C18	0.31135 (14)	−0.16039 (19)	0.27514 (5)	0.0354 (4)
H18	0.2822	−0.2390	0.2923	0.043*
C19	0.24920 (12)	−0.10478 (18)	0.24270 (4)	0.0293 (3)
H19	0.1772	−0.1434	0.2381	0.035*

	U11	U22	U33	U12	U13	U23
Cl1	0.0543 (3)	0.0950 (5)	0.0346 (2)	0.0261 (3)	0.0028 (2)	−0.0022 (3)
O1	0.0304 (5)	0.0214 (5)	0.0343 (6)	−0.0008 (5)	−0.0029 (4)	−0.0001 (5)
N1	0.0293 (6)	0.0238 (7)	0.0303 (6)	0.0018 (6)	−0.0084 (5)	−0.0012 (6)
N2	0.0295 (7)	0.0207 (6)	0.0361 (7)	−0.0033 (6)	−0.0097 (5)	0.0054 (6)
C1	0.0388 (9)	0.0465 (10)	0.0298 (8)	0.0157 (8)	−0.0022 (7)	0.0049 (8)
C2	0.0300 (8)	0.0476 (11)	0.0414 (9)	0.0029 (8)	0.0011 (7)	0.0082 (9)
C3	0.0303 (8)	0.0365 (9)	0.0396 (9)	−0.0018 (7)	−0.0046 (7)	−0.0005 (8)
C4	0.0274 (7)	0.0269 (8)	0.0290 (7)	0.0030 (7)	−0.0073 (6)	0.0041 (7)
C5	0.0300 (8)	0.0331 (9)	0.0350 (8)	−0.0003 (7)	−0.0070 (6)	0.0014 (7)
C6	0.0408 (9)	0.0412 (10)	0.0352 (8)	0.0044 (8)	−0.0113 (7)	−0.0056 (8)
C7	0.0254 (7)	0.0316 (9)	0.0324 (8)	−0.0024 (7)	−0.0056 (6)	−0.0017 (7)
C8	0.0354 (8)	0.0245 (8)	0.0345 (8)	0.0026 (7)	−0.0091 (7)	0.0022 (7)
C9	0.0495 (10)	0.0358 (10)	0.0454 (10)	0.0022 (8)	−0.0033 (8)	0.0120 (9)
C10	0.0705 (13)	0.0338 (10)	0.0552 (11)	0.0087 (10)	−0.0153 (10)	0.0118 (9)
C11	0.0532 (11)	0.0433 (12)	0.0730 (14)	0.0190 (10)	−0.0099 (10)	0.0020 (11)
C12	0.0459 (10)	0.0343 (9)	0.0459 (10)	0.0084 (8)	0.0025 (8)	−0.0006 (8)
C13	0.0231 (7)	0.0246 (8)	0.0269 (7)	−0.0011 (6)	0.0017 (6)	0.0016 (7)
C14	0.0265 (7)	0.0211 (7)	0.0290 (7)	0.0047 (6)	−0.0049 (6)	−0.0033 (6)
C15	0.0278 (8)	0.0253 (8)	0.0369 (8)	0.0015 (6)	−0.0026 (6)	−0.0027 (7)
C16	0.0271 (7)	0.0346 (9)	0.0454 (9)	0.0065 (7)	−0.0104 (7)	−0.0104 (8)
C17	0.0430 (9)	0.0375 (10)	0.0339 (8)	0.0145 (8)	−0.0141 (7)	−0.0038 (8)
C18	0.0440 (9)	0.0297 (9)	0.0326 (8)	0.0073 (8)	−0.0023 (7)	0.0018 (7)
C19	0.0286 (7)	0.0249 (8)	0.0342 (8)	0.0023 (7)	−0.0038 (6)	−0.0013 (7)

Cl1—C1	1.7478 (17)	C8—H8	1.0000
O1—C13	1.2382 (17)	C9—C10	1.521 (3)
N1—C13	1.3654 (18)	C9—H9A	0.9900
N1—C7	1.4604 (18)	C9—H9B	0.9900
N1—C8	1.474 (2)	C10—C11	1.525 (3)
N2—C13	1.3686 (19)	C10—H10A	0.9900
N2—C14	1.4141 (18)	C10—H10B	0.9900
N2—H2N	0.828 (19)	C11—C12	1.527 (3)
C1—C2	1.371 (2)	C11—H11A	0.9900
C1—C6	1.380 (2)	C11—H11B	0.9900
C2—C3	1.389 (2)	C12—H12A	0.9900
C2—H2	0.9500	C12—H12B	0.9900
C3—C4	1.387 (2)	C14—C19	1.384 (2)
C3—H3	0.9500	C14—C15	1.390 (2)
C4—C5	1.385 (2)	C15—C16	1.384 (2)
C4—C7	1.515 (2)	C15—H15	0.9500
C5—C6	1.381 (2)	C16—C17	1.380 (2)
C5—H5	0.9500	C16—H16	0.9500
C6—H6	0.9500	C17—C18	1.382 (2)
C7—H7A	0.9900	C17—H17	0.9500
C7—H7B	0.9900	C18—C19	1.387 (2)
C8—C9	1.520 (2)	C18—H18	0.9500
C8—C12	1.543 (2)	C19—H19	0.9500
C13—N1—C7	116.23 (12)	H9A—C9—H9B	109.0
C13—N1—C8	125.02 (12)	C9—C10—C11	104.42 (15)
C7—N1—C8	118.11 (12)	C9—C10—H10A	110.9
C13—N2—C14	124.07 (13)	C11—C10—H10A	110.9
C13—N2—H2N	117.8 (12)	C9—C10—H10B	110.9
C14—N2—H2N	116.5 (12)	C11—C10—H10B	110.9
C2—C1—C6	121.24 (15)	H10A—C10—H10B	108.9
C2—C1—Cl1	119.44 (13)	C10—C11—C12	106.55 (15)
C6—C1—Cl1	119.32 (14)	C10—C11—H11A	110.4
C1—C2—C3	119.13 (15)	C12—C11—H11A	110.4
C1—C2—H2	120.4	C10—C11—H11B	110.4
C3—C2—H2	120.4	C12—C11—H11B	110.4
C4—C3—C2	120.91 (15)	H11A—C11—H11B	108.6
C4—C3—H3	119.5	C11—C12—C8	105.99 (14)
C2—C3—H3	119.5	C11—C12—H12A	110.5
C5—C4—C3	118.45 (14)	C8—C12—H12A	110.5
C5—C4—C7	118.30 (13)	C11—C12—H12B	110.5
C3—C4—C7	123.23 (14)	C8—C12—H12B	110.5
C6—C5—C4	121.28 (15)	H12A—C12—H12B	108.7
C6—C5—H5	119.4	O1—C13—N1	120.78 (13)
C4—C5—H5	119.4	O1—C13—N2	122.27 (13)
C1—C6—C5	118.98 (16)	N1—C13—N2	116.96 (13)
C1—C6—H6	120.5	C19—C14—C15	119.46 (13)
C5—C6—H6	120.5	C19—C14—N2	122.10 (13)
N1—C7—C4	115.17 (12)	C15—C14—N2	118.31 (14)
N1—C7—H7A	108.5	C16—C15—C14	120.32 (15)
C4—C7—H7A	108.5	C16—C15—H15	119.8
N1—C7—H7B	108.5	C14—C15—H15	119.8
C4—C7—H7B	108.5	C17—C16—C15	120.21 (15)
H7A—C7—H7B	107.5	C17—C16—H16	119.9
N1—C8—C9	114.36 (13)	C15—C16—H16	119.9
N1—C8—C12	114.81 (13)	C16—C17—C18	119.51 (15)
C9—C8—C12	104.49 (13)	C16—C17—H17	120.2
N1—C8—H8	107.6	C18—C17—H17	120.2
C9—C8—H8	107.6	C17—C18—C19	120.64 (16)
C12—C8—H8	107.6	C17—C18—H18	119.7
C8—C9—C10	103.43 (14)	C19—C18—H18	119.7
C8—C9—H9A	111.1	C14—C19—C18	119.83 (14)
C10—C9—H9A	111.1	C14—C19—H19	120.1
C8—C9—H9B	111.1	C18—C19—H19	120.1
C10—C9—H9B	111.1
C6—C1—C2—C3	−0.2 (3)	C9—C10—C11—C12	24.7 (2)
Cl1—C1—C2—C3	179.54 (13)	C10—C11—C12—C8	−1.9 (2)
C1—C2—C3—C4	−0.2 (3)	N1—C8—C12—C11	−147.64 (15)
C2—C3—C4—C5	0.4 (2)	C9—C8—C12—C11	−21.56 (18)
C2—C3—C4—C7	−177.90 (15)	C7—N1—C13—O1	−6.1 (2)
C3—C4—C5—C6	−0.3 (2)	C8—N1—C13—O1	164.53 (14)
C7—C4—C5—C6	178.12 (14)	C7—N1—C13—N2	173.51 (12)
C2—C1—C6—C5	0.4 (3)	C8—N1—C13—N2	−15.8 (2)
Cl1—C1—C6—C5	−179.41 (12)	C14—N2—C13—O1	−13.1 (2)
C4—C5—C6—C1	−0.1 (2)	C14—N2—C13—N1	167.32 (13)
C13—N1—C7—C4	−81.80 (16)	C13—N2—C14—C19	−40.2 (2)
C8—N1—C7—C4	106.87 (15)	C13—N2—C14—C15	144.02 (15)
C5—C4—C7—N1	169.45 (13)	C19—C14—C15—C16	−1.1 (2)
C3—C4—C7—N1	−12.2 (2)	N2—C14—C15—C16	174.79 (14)
C13—N1—C8—C9	131.17 (15)	C14—C15—C16—C17	1.4 (2)
C7—N1—C8—C9	−58.34 (18)	C15—C16—C17—C18	−0.2 (2)
C13—N1—C8—C12	−108.04 (16)	C16—C17—C18—C19	−1.3 (2)
C7—N1—C8—C12	62.45 (18)	C15—C14—C19—C18	−0.3 (2)
N1—C8—C9—C10	163.14 (14)	N2—C14—C19—C18	−176.06 (14)
C12—C8—C9—C10	36.79 (18)	C17—C18—C19—C14	1.5 (2)
C8—C9—C10—C11	−38.08 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1i	0.828 (19)	2.081 (19)	2.8838 (17)	163.1 (17)

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N2H2NO1i	0.828(19)	2.081(19)	2.8838(17)	163.1(17)

Symmetry code: (i) .