Crystal structure of fenbuconazole.

In the title compound, C19H17ClN4 [systematic name: (RS)-4-(4-chloro-phen-yl)-2-phenyl-2-(1H-1,2,4-triazol-1-ylmeth-yl)butyro-nitrile], which is the conazole fungicide fenbuconazole, the dihedral angles between the planes of the central benzene and the terminal chloro-phenyl and triazole rings are 32.77 (5) and 32.97 (5)°, respectively. The C-C-C-C linkage between the tertiary C atom and the benzene ring has an anti orientation [torsion angle = 174.47 (12)°]. In the crystal, C-H⋯N hydrogen bonds and very weak C-Cl⋯π inter-actions [Cl⋯π = 3.7892 (9) Å] link adjacent mol-ecules, forming two-dimensional networks lying parellel to the (101) plane. The planes are linked by weak π-π inter-actions [centroid-centroid separation = 3.8597 (9) Å], resulting in a three-dimensional architecture.

Related literature

For information on the fungicidal properties of the title compound, see: Li et al. (2012 ▸). For related crystal structures, see: Rizzoli et al. (2009 ▸); Yin et al. (2014 ▸).

Experimental

Crystal data

C19H17ClN4

M = 336.82

Monoclinic,

a = 12.4606 (3) Å

b = 6.7404 (2) Å

c = 20.5394 (5) Å

β = 95.455 (2)°

V = 1717.28 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 173 K

0.18 × 0.07 × 0.03 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▸) T min = 0.959, T max = 0.993

15784 measured reflections

3936 independent reflections

3044 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.108

S = 1.04

3936 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2013 ▸); cell refinement: SAINT (Bruker, 2013 ▸); data reduction: SAINT; 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/S205698901501542X/hb7481sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S205698901501542X/hb7481Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S205698901501542X/hb7481Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S205698901501542X/hb7481fig1.tif

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

Click here for additional data file.

b . DOI: 10.1107/S205698901501542X/hb7481fig2.tif

Crystal packing viewed along the b axis. The inter­molecular inter­actions are shown as dashed lines.

CCDC reference: 1419334

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

C19H17ClN4	F(000) = 704
Mr = 336.82	Dx = 1.303 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.4606 (3) Å	Cell parameters from 3787 reflections
b = 6.7404 (2) Å	θ = 3.2–27.4°
c = 20.5394 (5) Å	µ = 0.23 mm−1
β = 95.455 (2)°	T = 173 K
V = 1717.28 (8) Å3	Plate, brown
Z = 4	0.18 × 0.07 × 0.03 mm

Bruker APEXII CCD diffractometer	3044 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.035
Absorption correction: multi-scan (SADABS; Bruker, 2013)	θmax = 27.5°, θmin = 1.8°
Tmin = 0.959, Tmax = 0.993	h = −15→16
15784 measured reflections	k = −8→8
3936 independent reflections	l = −26→26

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044	H-atom parameters constrained
wR(F2) = 0.108	w = 1/[σ2(Fo2) + (0.043P)2 + 0.4967P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
3936 reflections	Δρmax = 0.25 e Å−3
217 parameters	Δρmin = −0.30 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	0.02411 (4)	0.19334 (10)	1.12090 (3)	0.0689 (2)
N1	0.42210 (11)	1.1422 (2)	0.92410 (6)	0.0367 (3)
N2	0.63664 (9)	0.7989 (2)	0.86689 (5)	0.0277 (3)
N3	0.66105 (11)	0.9948 (2)	0.87314 (6)	0.0398 (3)
N4	0.71532 (12)	0.8721 (2)	0.77946 (7)	0.0445 (4)
C1	0.17939 (13)	0.3822 (3)	0.97206 (8)	0.0384 (4)
H1	0.2005	0.3286	0.9325	0.046*
C2	0.12369 (14)	0.2639 (3)	1.01229 (9)	0.0447 (4)
H2	0.1056	0.1311	1.0003	0.054*
C3	0.09501 (12)	0.3415 (3)	1.06994 (8)	0.0410 (4)
C4	0.12079 (14)	0.5320 (3)	1.08810 (8)	0.0485 (5)
H4	0.1014	0.5833	1.1284	0.058*
C5	0.17565 (13)	0.6493 (3)	1.04672 (8)	0.0398 (4)
H5	0.1933	0.7822	1.0589	0.048*
C6	0.20501 (10)	0.5763 (2)	0.98807 (7)	0.0278 (3)
C7	0.26520 (11)	0.7035 (3)	0.94298 (7)	0.0316 (3)
H7A	0.2559	0.8451	0.9541	0.038*
H7B	0.2341	0.6831	0.8973	0.038*
C8	0.38533 (11)	0.6541 (2)	0.94830 (6)	0.0237 (3)
H8A	0.3937	0.5096	0.9418	0.028*
H8B	0.4171	0.6864	0.9931	0.028*
C9	0.44939 (10)	0.7655 (2)	0.89855 (6)	0.0218 (3)
C10	0.41229 (10)	0.7205 (2)	0.82676 (6)	0.0229 (3)
C11	0.38360 (12)	0.5284 (2)	0.80795 (7)	0.0312 (3)
H11	0.3807	0.4280	0.8402	0.037*
C12	0.35906 (13)	0.4822 (3)	0.74246 (7)	0.0364 (4)
H12	0.3390	0.3506	0.7301	0.044*
C13	0.36370 (13)	0.6264 (3)	0.69533 (7)	0.0369 (4)
H13	0.3467	0.5943	0.6505	0.044*
C14	0.39293 (13)	0.8170 (3)	0.71325 (7)	0.0361 (4)
H14	0.3968	0.9162	0.6807	0.043*
C15	0.41687 (12)	0.8646 (2)	0.77900 (6)	0.0297 (3)
H15	0.4364	0.9967	0.7912	0.036*
C16	0.43710 (11)	0.9796 (2)	0.91178 (6)	0.0257 (3)
C17	0.56995 (11)	0.7062 (2)	0.91202 (6)	0.0255 (3)
H17A	0.5963	0.7450	0.9572	0.031*
H17B	0.5765	0.5603	0.9086	0.031*
C18	0.70813 (15)	1.0295 (3)	0.81948 (8)	0.0472 (5)
H18	0.7352	1.1567	0.8096	0.057*
C19	0.66923 (13)	0.7306 (3)	0.81087 (7)	0.0357 (4)
H19	0.6603	0.5979	0.7958	0.043*

	U11	U22	U33	U12	U13	U23
Cl1	0.0454 (3)	0.0820 (4)	0.0822 (4)	−0.0076 (3)	0.0220 (2)	0.0428 (3)
N1	0.0555 (8)	0.0248 (8)	0.0306 (7)	0.0036 (7)	0.0081 (6)	0.0001 (6)
N2	0.0283 (6)	0.0304 (7)	0.0253 (6)	−0.0013 (5)	0.0069 (5)	0.0004 (5)
N3	0.0489 (8)	0.0351 (8)	0.0384 (7)	−0.0131 (7)	0.0195 (6)	−0.0055 (6)
N4	0.0514 (8)	0.0463 (10)	0.0397 (7)	−0.0003 (7)	0.0240 (6)	0.0004 (7)
C1	0.0448 (9)	0.0389 (10)	0.0317 (8)	−0.0065 (8)	0.0057 (6)	−0.0035 (7)
C2	0.0441 (9)	0.0366 (10)	0.0529 (10)	−0.0123 (8)	0.0020 (8)	0.0032 (8)
C3	0.0275 (7)	0.0508 (12)	0.0455 (9)	−0.0038 (8)	0.0086 (6)	0.0185 (8)
C4	0.0521 (10)	0.0585 (13)	0.0388 (9)	−0.0014 (10)	0.0241 (8)	0.0008 (9)
C5	0.0474 (9)	0.0360 (10)	0.0382 (8)	−0.0064 (8)	0.0164 (7)	−0.0052 (7)
C6	0.0231 (6)	0.0334 (9)	0.0271 (7)	0.0002 (6)	0.0036 (5)	0.0036 (6)
C7	0.0317 (7)	0.0344 (9)	0.0297 (7)	0.0026 (7)	0.0084 (6)	0.0068 (7)
C8	0.0299 (7)	0.0226 (8)	0.0193 (6)	−0.0001 (6)	0.0054 (5)	0.0023 (6)
C9	0.0274 (6)	0.0185 (7)	0.0200 (6)	0.0006 (6)	0.0053 (5)	0.0021 (5)
C10	0.0243 (6)	0.0246 (8)	0.0202 (6)	0.0026 (6)	0.0046 (5)	0.0004 (6)
C11	0.0427 (8)	0.0269 (9)	0.0245 (7)	0.0000 (7)	0.0055 (6)	0.0024 (6)
C12	0.0482 (9)	0.0306 (9)	0.0302 (8)	0.0004 (8)	0.0024 (6)	−0.0069 (7)
C13	0.0427 (8)	0.0468 (11)	0.0208 (7)	0.0091 (8)	0.0014 (6)	−0.0042 (7)
C14	0.0465 (9)	0.0397 (10)	0.0223 (7)	0.0063 (8)	0.0045 (6)	0.0075 (7)
C15	0.0385 (8)	0.0267 (9)	0.0242 (7)	0.0014 (7)	0.0036 (6)	0.0038 (6)
C16	0.0334 (7)	0.0257 (9)	0.0186 (6)	−0.0012 (7)	0.0053 (5)	0.0032 (6)
C17	0.0288 (7)	0.0262 (8)	0.0220 (6)	0.0010 (6)	0.0048 (5)	0.0036 (6)
C18	0.0574 (11)	0.0420 (11)	0.0467 (9)	−0.0119 (9)	0.0284 (8)	−0.0007 (8)
C19	0.0392 (8)	0.0379 (10)	0.0322 (8)	0.0044 (7)	0.0142 (6)	−0.0043 (7)

Cl1—C3	1.7461 (16)	C8—C9	1.5492 (18)
N1—C16	1.1445 (19)	C8—H8A	0.9900
N2—C19	1.3376 (18)	C8—H8B	0.9900
N2—N3	1.3585 (18)	C9—C16	1.479 (2)
N2—C17	1.4444 (17)	C9—C10	1.5332 (17)
N3—C18	1.3178 (19)	C9—C17	1.5537 (18)
N4—C19	1.314 (2)	C10—C15	1.386 (2)
N4—C18	1.351 (2)	C10—C11	1.388 (2)
C1—C6	1.379 (2)	C11—C12	1.386 (2)
C1—C2	1.382 (2)	C11—H11	0.9500
C1—H1	0.9500	C12—C13	1.377 (2)
C2—C3	1.372 (2)	C12—H12	0.9500
C2—H2	0.9500	C13—C14	1.376 (2)
C3—C4	1.367 (3)	C13—H13	0.9500
C4—C5	1.388 (2)	C14—C15	1.392 (2)
C4—H4	0.9500	C14—H14	0.9500
C5—C6	1.382 (2)	C15—H15	0.9500
C5—H5	0.9500	C17—H17A	0.9900
C6—C7	1.5124 (19)	C17—H17B	0.9900
C7—C8	1.5273 (19)	C18—H18	0.9500
C7—H7A	0.9900	C19—H19	0.9500
C7—H7B	0.9900
C19—N2—N3	109.39 (12)	C16—C9—C8	106.43 (11)
C19—N2—C17	130.06 (14)	C10—C9—C8	114.28 (11)
N3—N2—C17	119.81 (12)	C16—C9—C17	109.49 (12)
C18—N3—N2	101.96 (13)	C10—C9—C17	108.56 (10)
C19—N4—C18	102.36 (13)	C8—C9—C17	107.94 (10)
C6—C1—C2	121.52 (15)	C15—C10—C11	118.93 (13)
C6—C1—H1	119.2	C15—C10—C9	120.87 (13)
C2—C1—H1	119.2	C11—C10—C9	119.90 (12)
C3—C2—C1	118.87 (17)	C12—C11—C10	120.47 (14)
C3—C2—H2	120.6	C12—C11—H11	119.8
C1—C2—H2	120.6	C10—C11—H11	119.8
C4—C3—C2	121.31 (15)	C13—C12—C11	120.22 (16)
C4—C3—Cl1	119.53 (14)	C13—C12—H12	119.9
C2—C3—Cl1	119.16 (15)	C11—C12—H12	119.9
C3—C4—C5	119.02 (16)	C14—C13—C12	119.92 (14)
C3—C4—H4	120.5	C14—C13—H13	120.0
C5—C4—H4	120.5	C12—C13—H13	120.0
C6—C5—C4	121.15 (17)	C13—C14—C15	120.11 (14)
C6—C5—H5	119.4	C13—C14—H14	119.9
C4—C5—H5	119.4	C15—C14—H14	119.9
C1—C6—C5	118.10 (14)	C10—C15—C14	120.35 (15)
C1—C6—C7	120.59 (13)	C10—C15—H15	119.8
C5—C6—C7	121.30 (15)	C14—C15—H15	119.8
C6—C7—C8	111.85 (12)	N1—C16—C9	175.67 (15)
C6—C7—H7A	109.2	N2—C17—C9	112.33 (11)
C8—C7—H7A	109.2	N2—C17—H17A	109.1
C6—C7—H7B	109.2	C9—C17—H17A	109.1
C8—C7—H7B	109.2	N2—C17—H17B	109.1
H7A—C7—H7B	107.9	C9—C17—H17B	109.1
C7—C8—C9	114.21 (11)	H17A—C17—H17B	107.9
C7—C8—H8A	108.7	N3—C18—N4	115.46 (16)
C9—C8—H8A	108.7	N3—C18—H18	122.3
C7—C8—H8B	108.7	N4—C18—H18	122.3
C9—C8—H8B	108.7	N4—C19—N2	110.83 (15)
H8A—C8—H8B	107.6	N4—C19—H19	124.6
C16—C9—C10	110.05 (11)	N2—C19—H19	124.6
C19—N2—N3—C18	−0.44 (17)	C16—C9—C10—C11	−159.29 (13)
C17—N2—N3—C18	−171.49 (14)	C8—C9—C10—C11	−39.62 (17)
C6—C1—C2—C3	−1.1 (3)	C17—C9—C10—C11	80.90 (15)
C1—C2—C3—C4	−0.2 (3)	C15—C10—C11—C12	−0.5 (2)
C1—C2—C3—Cl1	179.73 (13)	C9—C10—C11—C12	−174.29 (13)
C2—C3—C4—C5	1.0 (3)	C10—C11—C12—C13	0.5 (2)
Cl1—C3—C4—C5	−178.99 (14)	C11—C12—C13—C14	0.1 (2)
C3—C4—C5—C6	−0.4 (3)	C12—C13—C14—C15	−0.6 (2)
C2—C1—C6—C5	1.5 (2)	C11—C10—C15—C14	0.0 (2)
C2—C1—C6—C7	−179.47 (15)	C9—C10—C15—C14	173.75 (13)
C4—C5—C6—C1	−0.8 (2)	C13—C14—C15—C10	0.5 (2)
C4—C5—C6—C7	−179.76 (15)	C19—N2—C17—C9	−94.71 (18)
C1—C6—C7—C8	−77.25 (17)	N3—N2—C17—C9	74.23 (16)
C5—C6—C7—C8	101.70 (17)	C16—C9—C17—N2	−65.98 (14)
C6—C7—C8—C9	174.47 (12)	C10—C9—C17—N2	54.17 (16)
C7—C8—C9—C16	60.28 (15)	C8—C9—C17—N2	178.56 (11)
C7—C8—C9—C10	−61.39 (16)	N2—N3—C18—N4	0.2 (2)
C7—C8—C9—C17	177.73 (12)	C19—N4—C18—N3	0.0 (2)
C16—C9—C10—C15	27.07 (17)	C18—N4—C19—N2	−0.34 (19)
C8—C9—C10—C15	146.73 (13)	N3—N2—C19—N4	0.52 (18)
C17—C9—C10—C15	−92.74 (15)	C17—N2—C19—N4	170.36 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···N1i	0.99	2.53	3.522 (2)	178
C11—H11···N1i	0.95	2.60	3.533 (2)	166
C17—H17A···N1ii	0.99	2.58	3.5101 (18)	156
C18—H18···N4iii	0.95	2.46	3.277 (2)	144

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C8H8AN1i	0.99	2.53	3.522(2)	178
C11H11N1i	0.95	2.60	3.533(2)	166
C17H17AN1ii	0.99	2.58	3.5101(18)	156
C18H18N4iii	0.95	2.46	3.277(2)	144

Symmetry codes: (i) ; (ii) ; (iii) .