1-(4-Bromo-phen-yl)-2-{5-[(3,5-dimethyl-1H-pyrazol-1-yl)meth-yl]-4-phenyl-4H-1,2,4-triazol-3-ylsulfan-yl}ethanone.

The title compound, C(22)H(20)BrN(5)OS, is a potent new fungicide. The planes of the phenyl and pyrozole rings are almost perpendicular, making a dihedral angle of 86.5 (4)°. There are two non-classical inter-molecular C-H⋯O and C-H⋯N hydrogen bonds in the crystal structure.

Related literature

For background to heterocyclic compounds, see: Gong et al. (2008 ▶); Liu et al. (2007 ▶). For the synthesis, see: He et al. (2008 ▶).

Experimental

Crystal data

C22H20BrN5OS

M = 482.40

Triclinic,

a = 8.705 (2) Å

b = 9.173 (2) Å

c = 14.564 (4) Å

α = 94.561 (4)°

β = 97.659 (4)°

γ = 103.086 (4)°

V = 1115.3 (5) Å3

Z = 2

Mo Kα radiation

μ = 1.96 mm−1

T = 294 (2) K

0.28 × 0.24 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.592, T max = 0.674

5704 measured reflections

3914 independent reflections

2419 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.101

S = 1.02

3914 reflections

273 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.37 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809000403/bq2115sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809000403/bq2115Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C22H20BrN5OS	Z = 2
Mr = 482.40	F(000) = 492
Triclinic, P1	Dx = 1.436 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.705 (2) Å	Cell parameters from 1669 reflections
b = 9.173 (2) Å	θ = 2.6–23.0°
c = 14.564 (4) Å	µ = 1.96 mm−1
α = 94.561 (4)°	T = 294 K
β = 97.659 (4)°	Rhombic, colorless
γ = 103.086 (4)°	0.28 × 0.24 × 0.20 mm
V = 1115.3 (5) Å3

Bruker SMART CCD area-detector diffractometer	3914 independent reflections
Radiation source: fine-focus sealed tube	2419 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.592, Tmax = 0.674	k = −10→10
5704 measured reflections	l = −17→6

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0351P)2 + 0.4689P] where P = (Fo2 + 2Fc2)/3
3914 reflections	(Δ/σ)max = 0.001
273 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.37 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.

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.

	x	y	z	Uiso*/Ueq
Br1	0.29289 (6)	0.67651 (6)	−0.50744 (3)	0.0905 (2)
S1	0.55698 (11)	0.71293 (10)	0.09603 (6)	0.0490 (3)
O1	0.6651 (3)	0.6235 (2)	−0.07550 (16)	0.0513 (6)
N1	1.0999 (3)	1.1534 (3)	0.3101 (2)	0.0510 (7)
N2	1.1688 (3)	1.0707 (3)	0.25343 (19)	0.0454 (7)
N3	0.8643 (4)	1.0825 (3)	0.07347 (19)	0.0501 (7)
N4	0.7096 (3)	0.9911 (3)	0.05655 (19)	0.0499 (7)
N5	0.8674 (3)	0.8715 (3)	0.13335 (16)	0.0364 (6)
C1	1.1192 (6)	1.2185 (5)	0.4789 (3)	0.0941 (15)
H1A	1.0703	1.2973	0.4597	0.141*
H1B	1.2134	1.2611	0.5236	0.141*
H1C	1.0455	1.1474	0.5066	0.141*
C2	1.1639 (5)	1.1397 (4)	0.3953 (3)	0.0590 (10)
C3	1.2727 (5)	1.0505 (4)	0.3942 (3)	0.0640 (11)
H3	1.3327	1.0254	0.4456	0.077*
C4	1.2744 (4)	1.0070 (4)	0.3029 (3)	0.0548 (10)
C5	1.3679 (5)	0.9113 (5)	0.2587 (3)	0.0835 (14)
H5A	1.2977	0.8172	0.2309	0.125*
H5B	1.4481	0.8926	0.3052	0.125*
H5C	1.4182	0.9623	0.2115	0.125*
C6	1.1288 (4)	1.0667 (4)	0.1533 (2)	0.0507 (9)
H6A	1.1863	1.0030	0.1228	0.061*
H6B	1.1632	1.1676	0.1360	0.061*
C7	0.9553 (4)	1.0093 (3)	0.1199 (2)	0.0405 (8)
C8	0.7156 (4)	0.8664 (3)	0.0931 (2)	0.0398 (8)
C9	0.9262 (4)	0.7495 (3)	0.1701 (2)	0.0363 (7)
C10	0.9932 (4)	0.6635 (4)	0.1140 (3)	0.0571 (10)
H10	1.0027	0.6845	0.0533	0.069*
C11	1.0469 (5)	0.5443 (4)	0.1486 (3)	0.0730 (12)
H11	1.0928	0.4846	0.1112	0.088*
C12	1.0322 (5)	0.5149 (4)	0.2383 (3)	0.0658 (11)
H12	1.0665	0.4340	0.2613	0.079*
C13	0.9675 (5)	0.6034 (4)	0.2940 (3)	0.0635 (11)
H13	0.9603	0.5840	0.3552	0.076*
C14	0.9126 (4)	0.7216 (4)	0.2602 (2)	0.0514 (9)
H14	0.8671	0.7813	0.2978	0.062*
C15	0.4513 (4)	0.7061 (4)	−0.0201 (2)	0.0461 (9)
H15A	0.3481	0.6353	−0.0262	0.055*
H15B	0.4326	0.8047	−0.0291	0.055*
C16	0.5408 (4)	0.6597 (3)	−0.0953 (2)	0.0395 (8)
C17	0.4720 (4)	0.6607 (3)	−0.1940 (2)	0.0420 (8)
C18	0.3491 (4)	0.7294 (4)	−0.2204 (2)	0.0509 (9)
H18	0.3023	0.7726	−0.1749	0.061*
C19	0.2954 (4)	0.7345 (4)	−0.3134 (3)	0.0587 (10)
H19	0.2140	0.7820	−0.3308	0.070*
C20	0.3635 (5)	0.6689 (4)	−0.3794 (2)	0.0557 (10)
C21	0.4837 (5)	0.5963 (4)	−0.3557 (3)	0.0638 (11)
H21	0.5276	0.5505	−0.4015	0.077*
C22	0.5363 (4)	0.5937 (4)	−0.2631 (3)	0.0547 (10)
H22	0.6173	0.5457	−0.2463	0.066*

	U11	U22	U33	U12	U13	U23
Br1	0.1110 (4)	0.1126 (4)	0.0534 (3)	0.0427 (3)	0.0014 (3)	0.0149 (3)
S1	0.0501 (6)	0.0487 (5)	0.0493 (5)	0.0125 (4)	0.0070 (4)	0.0112 (4)
O1	0.0395 (14)	0.0570 (15)	0.0614 (15)	0.0204 (12)	0.0066 (12)	0.0070 (12)
N1	0.0537 (19)	0.0510 (18)	0.0496 (19)	0.0163 (15)	0.0084 (15)	0.0027 (15)
N2	0.0429 (17)	0.0426 (16)	0.0494 (18)	0.0079 (14)	0.0068 (14)	0.0046 (14)
N3	0.067 (2)	0.0359 (16)	0.0486 (17)	0.0156 (16)	0.0042 (16)	0.0102 (14)
N4	0.058 (2)	0.0389 (17)	0.0548 (18)	0.0192 (16)	0.0013 (15)	0.0076 (14)
N5	0.0454 (17)	0.0327 (15)	0.0344 (15)	0.0150 (13)	0.0064 (13)	0.0061 (12)
C1	0.111 (4)	0.114 (4)	0.057 (3)	0.031 (3)	0.015 (3)	−0.008 (3)
C2	0.063 (3)	0.059 (2)	0.052 (2)	0.011 (2)	0.007 (2)	0.005 (2)
C3	0.068 (3)	0.059 (3)	0.058 (3)	0.013 (2)	−0.010 (2)	0.011 (2)
C4	0.045 (2)	0.043 (2)	0.074 (3)	0.0081 (18)	0.004 (2)	0.005 (2)
C5	0.067 (3)	0.070 (3)	0.117 (4)	0.033 (2)	0.003 (3)	−0.001 (3)
C6	0.057 (2)	0.048 (2)	0.047 (2)	0.0074 (18)	0.0164 (18)	0.0065 (17)
C7	0.050 (2)	0.0356 (19)	0.0362 (18)	0.0082 (17)	0.0104 (16)	0.0041 (15)
C8	0.051 (2)	0.0351 (19)	0.0361 (18)	0.0185 (17)	0.0032 (16)	0.0019 (15)
C9	0.0392 (19)	0.0319 (17)	0.0402 (19)	0.0122 (15)	0.0063 (15)	0.0078 (15)
C10	0.072 (3)	0.056 (2)	0.052 (2)	0.033 (2)	0.012 (2)	0.0057 (19)
C11	0.085 (3)	0.059 (3)	0.085 (3)	0.043 (2)	0.010 (3)	0.000 (2)
C12	0.064 (3)	0.048 (2)	0.087 (3)	0.023 (2)	−0.005 (2)	0.024 (2)
C13	0.076 (3)	0.063 (3)	0.055 (2)	0.020 (2)	0.006 (2)	0.027 (2)
C14	0.062 (2)	0.054 (2)	0.044 (2)	0.0220 (19)	0.0124 (18)	0.0119 (17)
C15	0.044 (2)	0.043 (2)	0.053 (2)	0.0147 (17)	0.0041 (17)	0.0054 (16)
C16	0.036 (2)	0.0261 (17)	0.055 (2)	0.0050 (15)	0.0059 (17)	0.0036 (15)
C17	0.040 (2)	0.0376 (19)	0.048 (2)	0.0095 (16)	0.0066 (17)	0.0050 (16)
C18	0.050 (2)	0.054 (2)	0.051 (2)	0.0198 (19)	0.0067 (18)	−0.0005 (18)
C19	0.058 (2)	0.059 (2)	0.063 (3)	0.027 (2)	−0.002 (2)	0.007 (2)
C20	0.061 (2)	0.058 (2)	0.048 (2)	0.013 (2)	0.006 (2)	0.0078 (19)
C21	0.069 (3)	0.077 (3)	0.052 (2)	0.029 (2)	0.014 (2)	0.002 (2)
C22	0.054 (2)	0.060 (2)	0.057 (2)	0.027 (2)	0.0087 (19)	0.0051 (19)

Br1—C20	1.896 (3)	C6—H6B	0.9700
S1—C8	1.742 (3)	C9—C10	1.365 (4)
S1—C15	1.803 (3)	C9—C14	1.372 (4)
O1—C16	1.208 (3)	C10—C11	1.387 (5)
N1—C2	1.319 (4)	C10—H10	0.9300
N1—N2	1.362 (4)	C11—C12	1.371 (5)
N2—C4	1.356 (4)	C11—H11	0.9300
N2—C6	1.449 (4)	C12—C13	1.363 (5)
N3—C7	1.306 (4)	C12—H12	0.9300
N3—N4	1.395 (4)	C13—C14	1.380 (5)
N4—C8	1.308 (4)	C13—H13	0.9300
N5—C8	1.361 (4)	C14—H14	0.9300
N5—C7	1.365 (4)	C15—C16	1.514 (4)
N5—C9	1.443 (4)	C15—H15A	0.9700
C1—C2	1.506 (5)	C15—H15B	0.9700
C1—H1A	0.9600	C16—C17	1.484 (4)
C1—H1B	0.9600	C17—C22	1.382 (4)
C1—H1C	0.9600	C17—C18	1.387 (4)
C2—C3	1.385 (5)	C18—C19	1.381 (5)
C3—C4	1.360 (5)	C18—H18	0.9300
C3—H3	0.9300	C19—C20	1.363 (5)
C4—C5	1.491 (5)	C19—H19	0.9300
C5—H5A	0.9600	C20—C21	1.382 (5)
C5—H5B	0.9600	C21—C22	1.369 (5)
C5—H5C	0.9600	C21—H21	0.9300
C6—C7	1.483 (5)	C22—H22	0.9300
C6—H6A	0.9700
C8—S1—C15	98.77 (15)	C10—C9—N5	119.1 (3)
C2—N1—N2	104.6 (3)	C14—C9—N5	119.5 (3)
C4—N2—N1	111.8 (3)	C9—C10—C11	119.2 (3)
C4—N2—C6	129.2 (3)	C9—C10—H10	120.4
N1—N2—C6	118.9 (3)	C11—C10—H10	120.4
C7—N3—N4	107.4 (3)	C12—C11—C10	119.7 (4)
C8—N4—N3	106.9 (3)	C12—C11—H11	120.1
C8—N5—C7	105.1 (2)	C10—C11—H11	120.1
C8—N5—C9	127.1 (3)	C13—C12—C11	120.4 (3)
C7—N5—C9	127.3 (3)	C13—C12—H12	119.8
C2—C1—H1A	109.5	C11—C12—H12	119.8
C2—C1—H1B	109.5	C12—C13—C14	120.4 (4)
H1A—C1—H1B	109.5	C12—C13—H13	119.8
C2—C1—H1C	109.5	C14—C13—H13	119.8
H1A—C1—H1C	109.5	C9—C14—C13	118.9 (3)
H1B—C1—H1C	109.5	C9—C14—H14	120.6
N1—C2—C3	111.3 (3)	C13—C14—H14	120.6
N1—C2—C1	120.7 (4)	C16—C15—S1	112.9 (2)
C3—C2—C1	127.9 (4)	C16—C15—H15A	109.0
C4—C3—C2	106.4 (3)	S1—C15—H15A	109.0
C4—C3—H3	126.8	C16—C15—H15B	109.0
C2—C3—H3	126.8	S1—C15—H15B	109.0
N2—C4—C3	105.9 (3)	H15A—C15—H15B	107.8
N2—C4—C5	123.3 (4)	O1—C16—C17	120.9 (3)
C3—C4—C5	130.9 (4)	O1—C16—C15	121.0 (3)
C4—C5—H5A	109.5	C17—C16—C15	118.1 (3)
C4—C5—H5B	109.5	C22—C17—C18	118.4 (3)
H5A—C5—H5B	109.5	C22—C17—C16	118.5 (3)
C4—C5—H5C	109.5	C18—C17—C16	123.1 (3)
H5A—C5—H5C	109.5	C19—C18—C17	120.7 (3)
H5B—C5—H5C	109.5	C19—C18—H18	119.6
N2—C6—C7	112.5 (3)	C17—C18—H18	119.6
N2—C6—H6A	109.1	C20—C19—C18	119.0 (3)
C7—C6—H6A	109.1	C20—C19—H19	120.5
N2—C6—H6B	109.1	C18—C19—H19	120.5
C7—C6—H6B	109.1	C19—C20—C21	121.8 (3)
H6A—C6—H6B	107.8	C19—C20—Br1	119.6 (3)
N3—C7—N5	110.1 (3)	C21—C20—Br1	118.6 (3)
N3—C7—C6	125.2 (3)	C22—C21—C20	118.3 (3)
N5—C7—C6	124.7 (3)	C22—C21—H21	120.9
N4—C8—N5	110.5 (3)	C20—C21—H21	120.9
N4—C8—S1	127.3 (3)	C21—C22—C17	121.7 (3)
N5—C8—S1	122.2 (2)	C21—C22—H22	119.1
C10—C9—C14	121.4 (3)	C17—C22—H22	119.1
C2—N1—N2—C4	−0.2 (4)	C15—S1—C8—N5	−141.3 (3)
C2—N1—N2—C6	−177.5 (3)	C8—N5—C9—C10	93.5 (4)
C7—N3—N4—C8	−0.5 (3)	C7—N5—C9—C10	−76.7 (4)
N2—N1—C2—C3	0.3 (4)	C8—N5—C9—C14	−86.0 (4)
N2—N1—C2—C1	179.0 (3)	C7—N5—C9—C14	103.8 (4)
N1—C2—C3—C4	−0.2 (5)	C14—C9—C10—C11	0.7 (5)
C1—C2—C3—C4	−178.9 (4)	N5—C9—C10—C11	−178.7 (3)
N1—N2—C4—C3	0.0 (4)	C9—C10—C11—C12	−0.1 (6)
C6—N2—C4—C3	177.0 (3)	C10—C11—C12—C13	−1.1 (6)
N1—N2—C4—C5	−179.6 (3)	C11—C12—C13—C14	1.5 (6)
C6—N2—C4—C5	−2.6 (5)	C10—C9—C14—C13	−0.3 (5)
C2—C3—C4—N2	0.1 (4)	N5—C9—C14—C13	179.2 (3)
C2—C3—C4—C5	179.7 (4)	C12—C13—C14—C9	−0.9 (6)
C4—N2—C6—C7	124.9 (4)	C8—S1—C15—C16	68.2 (2)
N1—N2—C6—C7	−58.3 (4)	S1—C15—C16—O1	4.1 (4)
N4—N3—C7—N5	0.9 (3)	S1—C15—C16—C17	−175.6 (2)
N4—N3—C7—C6	−179.1 (3)	O1—C16—C17—C22	11.7 (5)
C8—N5—C7—N3	−0.9 (3)	C15—C16—C17—C22	−168.6 (3)
C9—N5—C7—N3	171.0 (3)	O1—C16—C17—C18	−166.4 (3)
C8—N5—C7—C6	179.0 (3)	C15—C16—C17—C18	13.2 (4)
C9—N5—C7—C6	−9.0 (5)	C22—C17—C18—C19	−1.8 (5)
N2—C6—C7—N3	122.0 (3)	C16—C17—C18—C19	176.3 (3)
N2—C6—C7—N5	−58.0 (4)	C17—C18—C19—C20	0.9 (5)
N3—N4—C8—N5	−0.1 (3)	C18—C19—C20—C21	0.6 (6)
N3—N4—C8—S1	178.2 (2)	C18—C19—C20—Br1	−179.3 (3)
C7—N5—C8—N4	0.6 (3)	C19—C20—C21—C22	−1.2 (6)
C9—N5—C8—N4	−171.4 (3)	Br1—C20—C21—C22	178.8 (3)
C7—N5—C8—S1	−177.8 (2)	C20—C21—C22—C17	0.3 (6)
C9—N5—C8—S1	10.3 (4)	C18—C17—C22—C21	1.2 (5)
C15—S1—C8—N4	40.6 (3)	C16—C17—C22—C21	−177.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6B···O1i	0.97	2.45	3.365 (3)	157
C15—H15B···N4ii	0.97	2.50	3.429 (3)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6B⋯O1i	0.97	2.45	3.365 (3)	157
C15—H15B⋯N4ii	0.97	2.50	3.429 (3)	161

Symmetry codes: (i) ; (ii) .