4-(4-Bromo-phen-yl)-1-(2,6-difluoro-benz-yl)-3-(3,4,5-trimeth-oxy-phen-yl)-1H-1,2,4-triazole-5(4H)-thione.

In the title compound, C(24)H(20)BrF(2)N(3)O(3)S, 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 trimeth-oxy-, bromo-, and difluoro-substituted benzene rings. The C atoms of the meta meth-oxy 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 R(2) (2)(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 = 548.40

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.158

S = 1.00

7051 reflections

310 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.44 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811052330/hb6551sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811052330/hb6551Isup3.cml

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

C24H20BrF2N3O3S	F(000) = 2224
Mr = 548.40	Dx = 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

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

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(Fo2) + (0.0774P)2] where P = (Fo2 + 2Fc2)/3
7051 reflections	(Δ/σ)max < 0.001
310 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.44 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	0.20988 (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*

	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)

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)

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

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) .