4-(4-Bromo­phen­yl)-1-(2,6-difluoro­benz­yl)-3-(3,4,5-trimeth­oxy­phen­yl)-1H-1,2,4-triazole-5(4H)-thione

Fun, H.-K.; Ooi, C.W.; Chandrakantha, B.; Isloor, A.M.; Shetty, P.

doi:10.1107/S1600536811052330

organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o89

doi:10.1107/S1600536811052330

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4-(4-Bromophenyl)-1-(2,6-difluorobenzyl)-3-(3,4,5-trimethoxyphenyl)-1H-1,2,4-triazole-5(4H)-thione

Hoong-Kun Fun,^a ^*‡ Chin Wei Ooi,^a B. Chandrakantha,^b Arun M. Isloor ^c and Prakash Shetty ^d

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Chemistry, Manipal Institute of Technology, Manipal 576 104, India, ^cMedicinal Chemistry Division, Department of Chemistry, National Institute of Technology-Karnataka, Surathkal, Mangalore 575 025, India, and ^dDepartment of Printing, Manipal Institute of Technology, Manipal 576 104, India
^*Correspondence e-mail: hkfun@usm.my

(Received 3 December 2011; accepted 4 December 2011; online 10 December 2011)

In the title compound, C₂₄H₂₀BrF₂N₃O₃S, the triazole ring (r.m.s. deviation = 0.0107 Å) makes dihedral angles of 28.18 (14), 63.76 (14) and 77.01 (18)°, respectively, with the trimethoxy-, bromo-, and difluoro-substituted benzene rings. The C atoms of the meta methoxy groups are roughly coplanar with their ring [displacements = −0.289 (4) and 0.083 (7) Å], whereas the C atom of the para group is displaced [1.117 (3) Å]. In the crystal, inversion dimers linked by two pairs of C—H⋯O hydrogen bonds occur. The ring motif of the two hydrogen bonds to their symmetry-generated O-atom acceptors is R₂²(8).

Related literature

For a related structure and background to 1,2,4-triazole derivatives, see: Fun et al. (2011 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₄H₂₀BrF₂N₃O₃S
M_r = 548.40
Monoclinic, C 2/c
a = 17.6694 (18) Å
b = 15.5299 (16) Å
c = 18.0855 (19) Å
β = 102.955 (2)°
V = 4836.4 (9) Å³
Z = 8
Mo Kα radiation
μ = 1.83 mm⁻¹
T = 296 K
0.63 × 0.34 × 0.21 mm

Data collection

Bruker APEX DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.391, T_max = 0.703
20567 measured reflections
7051 independent reflections
3435 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.158
S = 1.00
7051 reflections
310 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯O1ⁱ	0.93	2.54	3.284 (3)	137
C14—H14A⋯O2ⁱ	0.93	2.40	3.142 (3)	137
Symmetry code: (i) $[-x, y, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811052330/hb6551sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811052330/hb6551Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811052330/hb6551Isup3.cml

checkCIF report

Comment top

As part of our ongoing studies of 1,2,4-triazole derivatives (Fun et al., 2011), we now describe the structure of the title compound, (I).

In the title compound (Fig. 1), the triazole (N1–N3/C7/C8) ring is essentially planar with maximum deviation of 0.015 (3) Å at atom C8. The central triazole ring makes dihedral angles of 28.18 (14)°, 63.76 (14)° and 77.01 (18)° respectively with the methoxy (C1–C6), bromo (C9–C14), and difluoro (C16–C21) substituted phenyl rings. The bond lengths are comparable to a related structure (Fun et al., 2011).

In the crystal (Fig. 2), the intermolecular C13—H13A···O1 and C14—H14A···O2 hydrogen bonds (Table 1) link the molecules to form R₂² (8) ring motifs (Bernstein et al., 1995), leading to the formation of dimers.

Related literature top

For a related structure and background to 1,2,4-triazole derivatives, see: Fun et al. (2011). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

To a solution of 4-(4-bromophenyl)-5-(3,4,5-trimethoxyphenyl)-4H-1,2,4- triazole-3-thiol (1 g, 0.0023 mol) in dry acetonitrile (20 ml) was added potassium carbonate (0.65 g, 0.0047 mol) followed by 2,6-difluorobenzyl bromide (0.52 g, 0.0025 mol) at room temperature. After the addition, the reaction mixture was stirred at room temperature for 6 hr. Progress of reaction was monitored by TLC. After the completion of the reaction, the reaction mixture was concentrated and purified by column chromatography using pet ether, ethyl acetate as an eluent to afford title compound as a colourless solid. Yield 1.1 g, 85%. M.p: 448–453 K.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound, viewed down b axis. Dashed lines represent hydrogen bonds.

4-(4-Bromophenyl)-1-(2,6-difluorobenzyl)-3-(3,4,5-trimethoxyphenyl)-1H- 1,2,4-triazole-5(4H)-thione top

Crystal data top

C₂₄H₂₀BrF₂N₃O₃S	F(000) = 2224
M_r = 548.40	D_x = 1.506 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3384 reflections
a = 17.6694 (18) Å	θ = 2.3–22.8°
b = 15.5299 (16) Å	µ = 1.83 mm⁻¹
c = 18.0855 (19) Å	T = 296 K
β = 102.955 (2)°	Block, colourless
V = 4836.4 (9) Å³	0.63 × 0.34 × 0.21 mm
Z = 8

Data collection top

Bruker APEX DUO CCD diffractometer	7051 independent reflections
Radiation source: fine-focus sealed tube	3435 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
ϕ and ω scans	θ_max = 30.1°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −23→24
T_min = 0.391, T_max = 0.703	k = −21→20
20567 measured reflections	l = −25→25

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.158	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0774P)²] where P = (F_o² + 2F_c²)/3
7051 reflections	(Δ/σ)_max < 0.001
310 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

C₂₄H₂₀BrF₂N₃O₃S	V = 4836.4 (9) Å³
M_r = 548.40	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 17.6694 (18) Å	µ = 1.83 mm⁻¹
b = 15.5299 (16) Å	T = 296 K
c = 18.0855 (19) Å	0.63 × 0.34 × 0.21 mm
β = 102.955 (2)°

Data collection top

Bruker APEX DUO CCD diffractometer	7051 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3435 reflections with I > 2σ(I)
T_min = 0.391, T_max = 0.703	R_int = 0.041
20567 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.158	H-atom parameters constrained
S = 1.00	Δρ_max = 0.30 e Å⁻³
7051 reflections	Δρ_min = −0.44 e Å⁻³
310 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	0.20988 (3)	0.55993 (2)	0.21898 (3)	0.1130 (2)
S1	0.42133 (3)	0.87749 (5)	0.42274 (5)	0.0673 (2)
F1	0.32718 (17)	1.22282 (19)	0.4955 (2)	0.1545 (12)
F2	0.42211 (15)	0.98693 (17)	0.64170 (17)	0.1319 (10)
O1	−0.02973 (10)	0.76975 (11)	0.37056 (14)	0.0706 (6)
O2	−0.11356 (9)	0.91409 (13)	0.34642 (12)	0.0649 (5)
O3	−0.04768 (11)	1.06802 (12)	0.37062 (18)	0.0906 (8)
N1	0.26407 (10)	0.88186 (13)	0.41197 (11)	0.0444 (5)
N2	0.24694 (11)	1.00640 (14)	0.46509 (13)	0.0564 (6)
N3	0.32475 (11)	0.99013 (14)	0.46984 (13)	0.0557 (6)
C1	0.09112 (12)	0.85034 (16)	0.40263 (15)	0.0498 (6)
H1A	0.1210	0.8005	0.4104	0.060*
C2	0.01028 (13)	0.84511 (16)	0.38229 (15)	0.0520 (6)
C3	−0.03423 (13)	0.91950 (17)	0.37176 (16)	0.0536 (6)
C4	0.00131 (13)	0.99918 (17)	0.38142 (18)	0.0609 (7)
C5	0.08213 (14)	1.00515 (17)	0.40030 (18)	0.0599 (7)
H5A	0.1062	1.0588	0.4056	0.072*
C6	0.12633 (13)	0.93048 (15)	0.41108 (15)	0.0492 (6)
C7	0.21156 (13)	0.94011 (15)	0.43001 (15)	0.0487 (6)
C8	0.33770 (12)	0.91620 (17)	0.43633 (14)	0.0493 (6)
C9	0.24939 (12)	0.80534 (15)	0.36716 (13)	0.0428 (5)
C10	0.27705 (15)	0.72710 (18)	0.39855 (16)	0.0595 (7)
H10A	0.3036	0.7241	0.4491	0.071*
C11	0.26513 (18)	0.65378 (18)	0.35485 (18)	0.0694 (8)
H11A	0.2838	0.6010	0.3754	0.083*
C12	0.22515 (15)	0.65947 (17)	0.28023 (16)	0.0577 (7)
C13	0.19658 (14)	0.73658 (17)	0.24914 (15)	0.0544 (6)
H13A	0.1687	0.7391	0.1991	0.065*
C14	0.20950 (13)	0.81059 (15)	0.29267 (13)	0.0468 (6)
H14A	0.1914	0.8634	0.2718	0.056*
C15	0.38362 (16)	1.0561 (2)	0.49590 (19)	0.0726 (9)
H15A	0.3819	1.0975	0.4554	0.087*
H15B	0.4344	1.0292	0.5063	0.087*
C16	0.37404 (13)	1.10289 (16)	0.56521 (15)	0.0505 (6)
C17	0.34767 (18)	1.1854 (2)	0.5644 (2)	0.0794 (10)
C18	0.3428 (3)	1.2317 (3)	0.6272 (5)	0.125 (2)
H18A	0.3239	1.2878	0.6236	0.149*
C19	0.3670 (3)	1.1915 (4)	0.6960 (4)	0.130 (2)
H19A	0.3644	1.2215	0.7399	0.156*
C20	0.3937 (2)	1.1119 (4)	0.7023 (2)	0.1091 (15)
H20A	0.4101	1.0860	0.7495	0.131*
C21	0.39669 (18)	1.0688 (2)	0.6371 (2)	0.0739 (9)
C22	0.01256 (18)	0.69298 (18)	0.3665 (2)	0.0775 (9)
H22A	−0.0230	0.6465	0.3499	0.116*
H22B	0.0441	0.6799	0.4158	0.116*
H22C	0.0453	0.7006	0.3312	0.116*
C23	−0.15565 (16)	0.9151 (2)	0.4041 (2)	0.0742 (8)
H23A	−0.2103	0.9147	0.3816	0.111*
H23B	−0.1428	0.9661	0.4343	0.111*
H23C	−0.1425	0.8652	0.4357	0.111*
C24	−0.0154 (2)	1.1508 (2)	0.3820 (4)	0.1291 (19)
H24A	−0.0563	1.1929	0.3738	0.194*
H24B	0.0173	1.1606	0.3470	0.194*
H24C	0.0148	1.1557	0.4330	0.194*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.1658 (5)	0.0668 (2)	0.0968 (3)	0.0079 (2)	0.0091 (3)	−0.0314 (2)
S1	0.0325 (3)	0.0908 (5)	0.0767 (5)	0.0032 (3)	0.0079 (3)	−0.0227 (4)
F1	0.127 (2)	0.136 (2)	0.212 (3)	0.0421 (17)	0.065 (2)	0.094 (2)
F2	0.130 (2)	0.1086 (17)	0.160 (2)	0.0429 (15)	0.0390 (18)	0.0481 (17)
O1	0.0405 (9)	0.0573 (11)	0.1115 (17)	−0.0094 (8)	0.0114 (10)	−0.0154 (11)
O2	0.0308 (8)	0.0846 (12)	0.0747 (13)	−0.0053 (8)	0.0021 (8)	−0.0160 (11)
O3	0.0420 (10)	0.0622 (13)	0.159 (2)	0.0074 (9)	0.0055 (13)	−0.0095 (13)
N1	0.0295 (8)	0.0537 (11)	0.0469 (11)	−0.0002 (8)	0.0022 (8)	−0.0066 (9)
N2	0.0328 (9)	0.0679 (13)	0.0687 (14)	−0.0089 (9)	0.0119 (10)	−0.0213 (11)
N3	0.0308 (9)	0.0750 (14)	0.0608 (13)	−0.0074 (9)	0.0094 (9)	−0.0233 (12)
C1	0.0336 (11)	0.0548 (14)	0.0599 (16)	0.0018 (10)	0.0084 (11)	−0.0019 (12)
C2	0.0350 (11)	0.0592 (15)	0.0600 (16)	−0.0068 (11)	0.0068 (11)	−0.0103 (12)
C3	0.0296 (11)	0.0649 (15)	0.0623 (16)	−0.0018 (10)	0.0015 (11)	−0.0110 (13)
C4	0.0348 (12)	0.0562 (15)	0.087 (2)	0.0059 (11)	0.0041 (13)	−0.0115 (14)
C5	0.0379 (12)	0.0535 (14)	0.085 (2)	−0.0026 (11)	0.0075 (13)	−0.0096 (14)
C6	0.0303 (10)	0.0581 (14)	0.0578 (15)	−0.0025 (10)	0.0068 (10)	−0.0109 (12)
C7	0.0326 (11)	0.0568 (14)	0.0549 (15)	−0.0021 (10)	0.0063 (10)	−0.0113 (12)
C8	0.0308 (11)	0.0706 (16)	0.0440 (13)	−0.0032 (10)	0.0034 (10)	−0.0065 (12)
C9	0.0314 (10)	0.0508 (13)	0.0445 (13)	0.0033 (9)	0.0050 (10)	−0.0043 (11)
C10	0.0605 (15)	0.0619 (16)	0.0481 (15)	0.0093 (13)	−0.0046 (12)	0.0023 (13)
C11	0.082 (2)	0.0491 (15)	0.071 (2)	0.0130 (14)	0.0040 (16)	0.0051 (14)
C12	0.0579 (15)	0.0527 (14)	0.0610 (18)	0.0018 (12)	0.0101 (13)	−0.0101 (13)
C13	0.0507 (14)	0.0624 (16)	0.0452 (14)	−0.0022 (12)	0.0007 (11)	−0.0021 (12)
C14	0.0412 (12)	0.0486 (13)	0.0470 (14)	0.0024 (10)	0.0020 (11)	0.0019 (11)
C15	0.0457 (14)	0.099 (2)	0.077 (2)	−0.0327 (14)	0.0223 (14)	−0.0379 (17)
C16	0.0325 (11)	0.0570 (15)	0.0620 (17)	−0.0094 (10)	0.0105 (11)	−0.0123 (13)
C17	0.0631 (18)	0.0624 (18)	0.120 (3)	−0.0035 (15)	0.0364 (19)	0.007 (2)
C18	0.091 (3)	0.065 (2)	0.245 (7)	−0.025 (2)	0.095 (4)	−0.060 (4)
C19	0.088 (3)	0.165 (6)	0.155 (5)	−0.062 (4)	0.062 (4)	−0.102 (5)
C20	0.076 (2)	0.184 (5)	0.067 (2)	−0.029 (3)	0.0154 (19)	−0.026 (3)
C21	0.0535 (16)	0.088 (2)	0.080 (2)	−0.0048 (15)	0.0135 (15)	−0.0103 (19)
C22	0.0619 (17)	0.0548 (16)	0.112 (3)	−0.0076 (14)	0.0124 (17)	−0.0017 (17)
C23	0.0445 (14)	0.085 (2)	0.095 (2)	−0.0043 (14)	0.0199 (16)	−0.0046 (19)
C24	0.067 (2)	0.056 (2)	0.251 (6)	0.0080 (16)	0.009 (3)	0.000 (3)

Geometric parameters (Å, º) top

Br1—C12	1.885 (3)	C10—H10A	0.9300
S1—C8	1.664 (2)	C11—C12	1.379 (4)
F1—C17	1.349 (5)	C11—H11A	0.9300
F2—C21	1.344 (4)	C12—C13	1.370 (4)
O1—C2	1.359 (3)	C13—C14	1.383 (3)
O1—C22	1.418 (3)	C13—H13A	0.9300
O2—C3	1.376 (3)	C14—H14A	0.9300
O2—C23	1.411 (4)	C15—C16	1.491 (4)
O3—C4	1.362 (3)	C15—H15A	0.9700
O3—C24	1.403 (4)	C15—H15B	0.9700
N1—C8	1.384 (3)	C16—C17	1.363 (4)
N1—C7	1.386 (3)	C16—C21	1.378 (4)
N1—C9	1.429 (3)	C17—C18	1.363 (7)
N2—C7	1.294 (3)	C18—C19	1.372 (8)
N2—N3	1.381 (3)	C18—H18A	0.9300
N3—C8	1.342 (3)	C19—C20	1.319 (7)
N3—C15	1.461 (3)	C19—H19A	0.9300
C1—C6	1.384 (3)	C20—C21	1.367 (6)
C1—C2	1.395 (3)	C20—H20A	0.9300
C1—H1A	0.9300	C22—H22A	0.9600
C2—C3	1.386 (3)	C22—H22B	0.9600
C3—C4	1.381 (4)	C22—H22C	0.9600
C4—C5	1.395 (3)	C23—H23A	0.9600
C5—C6	1.387 (3)	C23—H23B	0.9600
C5—H5A	0.9300	C23—H23C	0.9600
C6—C7	1.475 (3)	C24—H24A	0.9600
C9—C14	1.376 (3)	C24—H24B	0.9600
C9—C10	1.383 (3)	C24—H24C	0.9600
C10—C11	1.375 (4)

C2—O1—C22	118.1 (2)	C12—C13—H13A	120.2
C3—O2—C23	114.8 (2)	C14—C13—H13A	120.2
C4—O3—C24	118.3 (2)	C9—C14—C13	119.4 (2)
C8—N1—C7	107.74 (19)	C9—C14—H14A	120.3
C8—N1—C9	122.63 (19)	C13—C14—H14A	120.3
C7—N1—C9	129.08 (17)	N3—C15—C16	114.0 (2)
C7—N2—N3	104.45 (19)	N3—C15—H15A	108.8
C8—N3—N2	113.36 (18)	C16—C15—H15A	108.8
C8—N3—C15	124.4 (2)	N3—C15—H15B	108.8
N2—N3—C15	121.2 (2)	C16—C15—H15B	108.8
C6—C1—C2	119.3 (2)	H15A—C15—H15B	107.7
C6—C1—H1A	120.3	C17—C16—C21	113.4 (3)
C2—C1—H1A	120.3	C17—C16—C15	123.5 (3)
O1—C2—C3	115.9 (2)	C21—C16—C15	122.8 (3)
O1—C2—C1	123.9 (2)	F1—C17—C18	119.2 (4)
C3—C2—C1	120.2 (2)	F1—C17—C16	115.8 (4)
O2—C3—C4	119.8 (2)	C18—C17—C16	124.9 (4)
O2—C3—C2	119.9 (2)	C17—C18—C19	116.8 (4)
C4—C3—C2	120.1 (2)	C17—C18—H18A	121.6
O3—C4—C3	115.4 (2)	C19—C18—H18A	121.6
O3—C4—C5	124.5 (2)	C20—C19—C18	122.5 (5)
C3—C4—C5	120.1 (2)	C20—C19—H19A	118.7
C6—C5—C4	119.5 (2)	C18—C19—H19A	118.7
C6—C5—H5A	120.3	C19—C20—C21	117.8 (5)
C4—C5—H5A	120.3	C19—C20—H20A	121.1
C1—C6—C5	120.7 (2)	C21—C20—H20A	121.1
C1—C6—C7	121.8 (2)	F2—C21—C20	119.1 (4)
C5—C6—C7	117.5 (2)	F2—C21—C16	116.4 (3)
N2—C7—N1	111.06 (19)	C20—C21—C16	124.5 (4)
N2—C7—C6	123.4 (2)	O1—C22—H22A	109.5
N1—C7—C6	125.6 (2)	O1—C22—H22B	109.5
N3—C8—N1	103.31 (19)	H22A—C22—H22B	109.5
N3—C8—S1	128.53 (17)	O1—C22—H22C	109.5
N1—C8—S1	128.1 (2)	H22A—C22—H22C	109.5
C14—C9—C10	120.7 (2)	H22B—C22—H22C	109.5
C14—C9—N1	119.6 (2)	O2—C23—H23A	109.5
C10—C9—N1	119.7 (2)	O2—C23—H23B	109.5
C11—C10—C9	119.8 (2)	H23A—C23—H23B	109.5
C11—C10—H10A	120.1	O2—C23—H23C	109.5
C9—C10—H10A	120.1	H23A—C23—H23C	109.5
C10—C11—C12	119.2 (2)	H23B—C23—H23C	109.5
C10—C11—H11A	120.4	O3—C24—H24A	109.5
C12—C11—H11A	120.4	O3—C24—H24B	109.5
C13—C12—C11	121.2 (2)	H24A—C24—H24B	109.5
C13—C12—Br1	119.0 (2)	O3—C24—H24C	109.5
C11—C12—Br1	119.8 (2)	H24A—C24—H24C	109.5
C12—C13—C14	119.6 (2)	H24B—C24—H24C	109.5

C7—N2—N3—C8	1.8 (3)	C15—N3—C8—S1	5.6 (4)
C7—N2—N3—C15	170.8 (3)	C7—N1—C8—N3	2.5 (3)
C22—O1—C2—C3	168.4 (3)	C9—N1—C8—N3	174.7 (2)
C22—O1—C2—C1	−10.7 (4)	C7—N1—C8—S1	−174.3 (2)
C6—C1—C2—O1	178.1 (3)	C9—N1—C8—S1	−2.1 (4)
C6—C1—C2—C3	−0.9 (4)	C8—N1—C9—C14	−110.9 (3)
C23—O2—C3—C4	−89.1 (3)	C7—N1—C9—C14	59.5 (3)
C23—O2—C3—C2	95.5 (3)	C8—N1—C9—C10	67.5 (3)
O1—C2—C3—O2	−3.8 (4)	C7—N1—C9—C10	−122.1 (3)
C1—C2—C3—O2	175.3 (2)	C14—C9—C10—C11	0.5 (4)
O1—C2—C3—C4	−179.2 (3)	N1—C9—C10—C11	−178.0 (2)
C1—C2—C3—C4	0.0 (4)	C9—C10—C11—C12	−0.4 (4)
C24—O3—C4—C3	177.9 (4)	C10—C11—C12—C13	−0.6 (5)
C24—O3—C4—C5	−2.6 (6)	C10—C11—C12—Br1	178.9 (2)
O2—C3—C4—O3	5.4 (4)	C11—C12—C13—C14	1.5 (4)
C2—C3—C4—O3	−179.2 (3)	Br1—C12—C13—C14	−177.93 (19)
O2—C3—C4—C5	−174.1 (3)	C10—C9—C14—C13	0.5 (4)
C2—C3—C4—C5	1.3 (5)	N1—C9—C14—C13	178.9 (2)
O3—C4—C5—C6	179.0 (3)	C12—C13—C14—C9	−1.5 (4)
C3—C4—C5—C6	−1.6 (5)	C8—N3—C15—C16	−146.7 (3)
C2—C1—C6—C5	0.7 (4)	N2—N3—C15—C16	45.6 (4)
C2—C1—C6—C7	−177.9 (2)	N3—C15—C16—C17	−106.4 (3)
C4—C5—C6—C1	0.6 (5)	N3—C15—C16—C21	78.7 (3)
C4—C5—C6—C7	179.2 (3)	C21—C16—C17—F1	177.9 (3)
N3—N2—C7—N1	−0.1 (3)	C15—C16—C17—F1	2.5 (4)
N3—N2—C7—C6	−178.9 (2)	C21—C16—C17—C18	−0.4 (4)
C8—N1—C7—N2	−1.6 (3)	C15—C16—C17—C18	−175.8 (3)
C9—N1—C7—N2	−173.1 (2)	F1—C17—C18—C19	−177.7 (4)
C8—N1—C7—C6	177.2 (3)	C16—C17—C18—C19	0.5 (6)
C9—N1—C7—C6	5.7 (4)	C17—C18—C19—C20	−0.1 (7)
C1—C6—C7—N2	−153.5 (3)	C18—C19—C20—C21	−0.3 (7)
C5—C6—C7—N2	27.9 (4)	C19—C20—C21—F2	−178.6 (3)
C1—C6—C7—N1	27.9 (4)	C19—C20—C21—C16	0.4 (6)
C5—C6—C7—N1	−150.7 (3)	C17—C16—C21—F2	178.9 (3)
N2—N3—C8—N1	−2.7 (3)	C15—C16—C21—F2	−5.7 (4)
C15—N3—C8—N1	−171.3 (3)	C17—C16—C21—C20	−0.1 (4)
N2—N3—C8—S1	174.1 (2)	C15—C16—C21—C20	175.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···O1ⁱ	0.93	2.54	3.284 (3)	137
C14—H14A···O2ⁱ	0.93	2.40	3.142 (3)	137

Symmetry code: (i) −x, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₀BrF₂N₃O₃S
M_r	548.40
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	17.6694 (18), 15.5299 (16), 18.0855 (19)
β (°)	102.955 (2)
V (Å³)	4836.4 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.83
Crystal size (mm)	0.63 × 0.34 × 0.21

Data collection
Diffractometer	Bruker APEX DUO CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.391, 0.703
No. of measured, independent and observed [I > 2σ(I)] reflections	20567, 7051, 3435
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.705

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.158, 1.00
No. of reflections	7051
No. of parameters	310
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.44

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···O1ⁱ	0.93	2.54	3.284 (3)	137
C14—H14A···O2ⁱ	0.93	2.40	3.142 (3)	137

Symmetry code: (i) −x, y, −z+1/2.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and CWO thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). CWO thanks the Malaysian Government and USM for the award of the post of research assistant under the Research University Grant (1001/PFIZIK/811151). AMI thanks the Board for Research in Nuclear Sciences, Department of Atomic Energy, Government of India, for the Young Scientist award.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fun, H.-K., Asik, S. I. J., Chandrakantha, B., Isloor, A. M. & Shetty, P. (2011). Acta Cryst. E67, o3422–o3423. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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

4-(4-Bromo­phen­yl)-1-(2,6-di­fluoro­benz­yl)-3-(3,4,5-trimeth­­oxy­phen­yl)-1H-1,2,4-triazole-5(4H)-thione

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

4-(4-Bromophenyl)-1-(2,6-difluorobenzyl)-3-(3,4,5-trimethoxyphenyl)-1H-1,2,4-triazole-5(4H)-thione