1-(4-Bromo­phen­yl)-2-{5-[(3,5-dimethyl-1H-pyrazol-1-yl)meth­yl]-4-phenyl-4H-1,2,4-triazol-3-ylsulfan­yl}ethanone

Xiao, S.-M.

doi:10.1107/S1600536809000403

organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o273

doi:10.1107/S1600536809000403

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1-(4-Bromophenyl)-2-{5-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]-4-phenyl-4H-1,2,4-triazol-3-ylsulfanyl}ethanone

Shan-Mei Xiao ^a ^*

^aCollege of Materials Science and Chemical Engineering, Jinhua College of Profession and Technology, Jinhua, Zhejiang 321017, People's Republic of China
^*Correspondence e-mail: xiaoshanmei@gmail.com

(Received 7 December 2008; accepted 6 January 2009; online 10 January 2009)

The title compound, C₂₂H₂₀BrN₅OS, 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 intermolecular 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_r = 482.40
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.041
wR(F²) = 0.101
S = 1.02
3914 reflections
273 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.37 e Å⁻³

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) -x+2, -y+2, -z; (ii) -x+1, -y+2, -z.

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.

Supporting information

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

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

checkCIF report

Comment top

A variety of pyrazole and triazole heterocyclics could exhibit many activities. Meanwhile, heterocyclic compounds is an important developmental direction in medical (Gong et al., 2008) and pesticidal (Liu et al., 2007) chemistry.

In view of these facts and in continuation of our interest in the agriculture, we attempted to synthesize a series of amide derivatives, some of which have comparatively high fungicidal activity.

The molecular structure of title compound is showing in Fig.1. The x-ray analysis reveals that acetyl group is a planar with thio-ether group. The pyrozole ring is vertical with the benzene ring [dihedral angle 93.5 (4)°]. The packing of the structure is due to the weak intermolecular C-H..O and C-H..N H-bonds (Table 1. and Fig 2.).

Related literature top

For background to heterocyclic compounds, see: Gong et al. (2008); Liu et al. (2007). For the synthesis of 5-((3,5-dimethyl-1H-pyrazol-1-yl)methyl)-4-phenyl-4H-1,2,4-triazole-3-thiol, see: He et al. (2008).

Experimental top

The compound 5-((3,5-Dimethyl-1H-pyrazol-1-yl)methyl)-4-phenyl-4H-1,2,4 -triazole-3-thiol was synthesized according to the reference (He et al., 2008). Then added p-bromo-phenacyl bromide, potassium carbonate anhydrous and N,N-Dimethyl formamide was stirred at room temperature for 5 h, giving the title compound. Colorless single crystals suitable for x-ray diffraction were obtained by recrystallization from a mixture of ethyl acetate and petroleum ether.

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of (I) with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. Partial packing diagram for (I). The dotted lines show the C—H–O bond.
	Fig. 3. The formation of the title compound.

1-(4-Bromophenyl)-2-{5-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]-4-phenyl- 4H-1,2,4-triazol-3-ylsulfanyl}ethanone top

Crystal data top

C₂₂H₂₀BrN₅OS	Z = 2
M_r = 482.40	F(000) = 492
Triclinic, P1	D_x = 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

Data collection top

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

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.101	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0351P)² + 0.4689P] where P = (F_o² + 2F_c²)/3
3914 reflections	(Δ/σ)_max = 0.001
273 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₂₂H₂₀BrN₅OS	γ = 103.086 (4)°
M_r = 482.40	V = 1115.3 (5) Å³
Triclinic, P1	Z = 2
a = 8.705 (2) Å	Mo Kα radiation
b = 9.173 (2) Å	µ = 1.96 mm⁻¹
c = 14.564 (4) Å	T = 294 K
α = 94.561 (4)°	0.28 × 0.24 × 0.20 mm
β = 97.659 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3914 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2419 reflections with I > 2σ(I)
T_min = 0.592, T_max = 0.674	R_int = 0.021
5704 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.101	H-atom parameters constrained
S = 1.02	Δρ_max = 0.39 e Å⁻³
3914 reflections	Δρ_min = −0.37 e Å⁻³
273 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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+2, −y+2, −z; (ii) −x+1, −y+2, −z.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₀BrN₅OS
M_r	482.40
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	8.705 (2), 9.173 (2), 14.564 (4)
α, β, γ (°)	94.561 (4), 97.659 (4), 103.086 (4)
V (Å³)	1115.3 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.96
Crystal size (mm)	0.28 × 0.24 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.592, 0.674
No. of measured, independent and observed [I > 2σ(I)] reflections	5704, 3914, 2419
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.101, 1.02
No. of reflections	3914
No. of parameters	273
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.37

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) −x+2, −y+2, −z; (ii) −x+1, −y+2, −z.

References

Bruker. (2004). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Gong, Y., Barbay, J. K., Buntinx, M., Li, J., Van Wauweb, J., Claes, C., Van Lommen, G., Hornby, P. J. & He, W. (2008). Bioorg. Med. Chem. Lett. 18, 3852–3855. Web of Science CrossRef PubMed CAS Google Scholar
He, F. Q., Liu, X. H., Wang, B. L. & Li, Z. M. (2008). Heteroat. Chem. 19, 21–27. Web of Science CrossRef CAS Google Scholar
Liu, X. H., Chen, P. Q., Wang, B. L., Li, Y. H., Wang, S. H. & Li, Z. M. (2007). Bioorg. Med. Chem. Lett. 17, 3784–3788. Web of Science CSD CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 65| Part 2| February 2009| Page o273

doi:10.1107/S1600536809000403

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

1-(4-Bromo­phen­yl)-2-{5-[(3,5-di­methyl-1H-pyrazol-1-yl)meth­yl]-4-phenyl-4H-1,2,4-triazol-3-ylsulfan­yl}ethanone

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Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

1-(4-Bromophenyl)-2-{5-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]-4-phenyl-4H-1,2,4-triazol-3-ylsulfanyl}ethanone