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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

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

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[Fun, H.-K., Asik, S. I. J., Chandrakantha, B., Isloor, A. M. & Shetty, P. (2011). Acta Cryst. E67, o3422-o3423.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C24H20BrF2N3O3S

  • Mr = 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[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.391, Tmax = 0.703

  • 20567 measured reflections

  • 7051 independent reflections

  • 3435 reflections with I > 2σ(I)

  • Rint = 0.041

Refinement
  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


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.

Refinement top

All the H atoms were positioned geometrically and refined using a riding model with Uiso(H) = 1.2 or 1.5Ueq(C) (C—H = 0.93, 0.96 or 0.97 Å). A rotating group model was applied to the methyl group. In the final refinement, one outliner (-2 0 8) was omitted.

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
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids.
[Figure 2] 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
C24H20BrF2N3O3SF(000) = 2224
Mr = 548.40Dx = 1.506 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 3384 reflections
a = 17.6694 (18) Åθ = 2.3–22.8°
b = 15.5299 (16) ŵ = 1.83 mm1
c = 18.0855 (19) ÅT = 296 K
β = 102.955 (2)°Block, colourless
V = 4836.4 (9) Å30.63 × 0.34 × 0.21 mm
Z = 8
Data collection top
Bruker APEX DUO CCD
diffractometer
7051 independent reflections
Radiation source: fine-focus sealed tube3435 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
ϕ and ω scansθmax = 30.1°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 2324
Tmin = 0.391, Tmax = 0.703k = 2120
20567 measured reflectionsl = 2525
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.158H-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 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.44 e Å3
Crystal data top
C24H20BrF2N3O3SV = 4836.4 (9) Å3
Mr = 548.40Z = 8
Monoclinic, C2/cMo Kα radiation
a = 17.6694 (18) ŵ = 1.83 mm1
b = 15.5299 (16) ÅT = 296 K
c = 18.0855 (19) Å0.63 × 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)
Tmin = 0.391, Tmax = 0.703Rint = 0.041
20567 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.158H-atom parameters constrained
S = 1.00Δρmax = 0.30 e Å3
7051 reflectionsΔρmin = 0.44 e Å3
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
xyzUiso*/Ueq
Br10.20988 (3)0.55993 (2)0.21898 (3)0.1130 (2)
S10.42133 (3)0.87749 (5)0.42274 (5)0.0673 (2)
F10.32718 (17)1.22282 (19)0.4955 (2)0.1545 (12)
F20.42211 (15)0.98693 (17)0.64170 (17)0.1319 (10)
O10.02973 (10)0.76975 (11)0.37056 (14)0.0706 (6)
O20.11356 (9)0.91409 (13)0.34642 (12)0.0649 (5)
O30.04768 (11)1.06802 (12)0.37062 (18)0.0906 (8)
N10.26407 (10)0.88186 (13)0.41197 (11)0.0444 (5)
N20.24694 (11)1.00640 (14)0.46509 (13)0.0564 (6)
N30.32475 (11)0.99013 (14)0.46984 (13)0.0557 (6)
C10.09112 (12)0.85034 (16)0.40263 (15)0.0498 (6)
H1A0.12100.80050.41040.060*
C20.01028 (13)0.84511 (16)0.38229 (15)0.0520 (6)
C30.03423 (13)0.91950 (17)0.37176 (16)0.0536 (6)
C40.00131 (13)0.99918 (17)0.38142 (18)0.0609 (7)
C50.08213 (14)1.00515 (17)0.40030 (18)0.0599 (7)
H5A0.10621.05880.40560.072*
C60.12633 (13)0.93048 (15)0.41108 (15)0.0492 (6)
C70.21156 (13)0.94011 (15)0.43001 (15)0.0487 (6)
C80.33770 (12)0.91620 (17)0.43633 (14)0.0493 (6)
C90.24939 (12)0.80534 (15)0.36716 (13)0.0428 (5)
C100.27705 (15)0.72710 (18)0.39855 (16)0.0595 (7)
H10A0.30360.72410.44910.071*
C110.26513 (18)0.65378 (18)0.35485 (18)0.0694 (8)
H11A0.28380.60100.37540.083*
C120.22515 (15)0.65947 (17)0.28023 (16)0.0577 (7)
C130.19658 (14)0.73658 (17)0.24914 (15)0.0544 (6)
H13A0.16870.73910.19910.065*
C140.20950 (13)0.81059 (15)0.29267 (13)0.0468 (6)
H14A0.19140.86340.27180.056*
C150.38362 (16)1.0561 (2)0.49590 (19)0.0726 (9)
H15A0.38191.09750.45540.087*
H15B0.43441.02920.50630.087*
C160.37404 (13)1.10289 (16)0.56521 (15)0.0505 (6)
C170.34767 (18)1.1854 (2)0.5644 (2)0.0794 (10)
C180.3428 (3)1.2317 (3)0.6272 (5)0.125 (2)
H18A0.32391.28780.62360.149*
C190.3670 (3)1.1915 (4)0.6960 (4)0.130 (2)
H19A0.36441.22150.73990.156*
C200.3937 (2)1.1119 (4)0.7023 (2)0.1091 (15)
H20A0.41011.08600.74950.131*
C210.39669 (18)1.0688 (2)0.6371 (2)0.0739 (9)
C220.01256 (18)0.69298 (18)0.3665 (2)0.0775 (9)
H22A0.02300.64650.34990.116*
H22B0.04410.67990.41580.116*
H22C0.04530.70060.33120.116*
C230.15565 (16)0.9151 (2)0.4041 (2)0.0742 (8)
H23A0.21030.91470.38160.111*
H23B0.14280.96610.43430.111*
H23C0.14250.86520.43570.111*
C240.0154 (2)1.1508 (2)0.3820 (4)0.1291 (19)
H24A0.05631.19290.37380.194*
H24B0.01731.16060.34700.194*
H24C0.01481.15570.43300.194*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.1658 (5)0.0668 (2)0.0968 (3)0.0079 (2)0.0091 (3)0.0314 (2)
S10.0325 (3)0.0908 (5)0.0767 (5)0.0032 (3)0.0079 (3)0.0227 (4)
F10.127 (2)0.136 (2)0.212 (3)0.0421 (17)0.065 (2)0.094 (2)
F20.130 (2)0.1086 (17)0.160 (2)0.0429 (15)0.0390 (18)0.0481 (17)
O10.0405 (9)0.0573 (11)0.1115 (17)0.0094 (8)0.0114 (10)0.0154 (11)
O20.0308 (8)0.0846 (12)0.0747 (13)0.0053 (8)0.0021 (8)0.0160 (11)
O30.0420 (10)0.0622 (13)0.159 (2)0.0074 (9)0.0055 (13)0.0095 (13)
N10.0295 (8)0.0537 (11)0.0469 (11)0.0002 (8)0.0022 (8)0.0066 (9)
N20.0328 (9)0.0679 (13)0.0687 (14)0.0089 (9)0.0119 (10)0.0213 (11)
N30.0308 (9)0.0750 (14)0.0608 (13)0.0074 (9)0.0094 (9)0.0233 (12)
C10.0336 (11)0.0548 (14)0.0599 (16)0.0018 (10)0.0084 (11)0.0019 (12)
C20.0350 (11)0.0592 (15)0.0600 (16)0.0068 (11)0.0068 (11)0.0103 (12)
C30.0296 (11)0.0649 (15)0.0623 (16)0.0018 (10)0.0015 (11)0.0110 (13)
C40.0348 (12)0.0562 (15)0.087 (2)0.0059 (11)0.0041 (13)0.0115 (14)
C50.0379 (12)0.0535 (14)0.085 (2)0.0026 (11)0.0075 (13)0.0096 (14)
C60.0303 (10)0.0581 (14)0.0578 (15)0.0025 (10)0.0068 (10)0.0109 (12)
C70.0326 (11)0.0568 (14)0.0549 (15)0.0021 (10)0.0063 (10)0.0113 (12)
C80.0308 (11)0.0706 (16)0.0440 (13)0.0032 (10)0.0034 (10)0.0065 (12)
C90.0314 (10)0.0508 (13)0.0445 (13)0.0033 (9)0.0050 (10)0.0043 (11)
C100.0605 (15)0.0619 (16)0.0481 (15)0.0093 (13)0.0046 (12)0.0023 (13)
C110.082 (2)0.0491 (15)0.071 (2)0.0130 (14)0.0040 (16)0.0051 (14)
C120.0579 (15)0.0527 (14)0.0610 (18)0.0018 (12)0.0101 (13)0.0101 (13)
C130.0507 (14)0.0624 (16)0.0452 (14)0.0022 (12)0.0007 (11)0.0021 (12)
C140.0412 (12)0.0486 (13)0.0470 (14)0.0024 (10)0.0020 (11)0.0019 (11)
C150.0457 (14)0.099 (2)0.077 (2)0.0327 (14)0.0223 (14)0.0379 (17)
C160.0325 (11)0.0570 (15)0.0620 (17)0.0094 (10)0.0105 (11)0.0123 (13)
C170.0631 (18)0.0624 (18)0.120 (3)0.0035 (15)0.0364 (19)0.007 (2)
C180.091 (3)0.065 (2)0.245 (7)0.025 (2)0.095 (4)0.060 (4)
C190.088 (3)0.165 (6)0.155 (5)0.062 (4)0.062 (4)0.102 (5)
C200.076 (2)0.184 (5)0.067 (2)0.029 (3)0.0154 (19)0.026 (3)
C210.0535 (16)0.088 (2)0.080 (2)0.0048 (15)0.0135 (15)0.0103 (19)
C220.0619 (17)0.0548 (16)0.112 (3)0.0076 (14)0.0124 (17)0.0017 (17)
C230.0445 (14)0.085 (2)0.095 (2)0.0043 (14)0.0199 (16)0.0046 (19)
C240.067 (2)0.056 (2)0.251 (6)0.0080 (16)0.009 (3)0.000 (3)
Geometric parameters (Å, º) top
Br1—C121.885 (3)C10—H10A0.9300
S1—C81.664 (2)C11—C121.379 (4)
F1—C171.349 (5)C11—H11A0.9300
F2—C211.344 (4)C12—C131.370 (4)
O1—C21.359 (3)C13—C141.383 (3)
O1—C221.418 (3)C13—H13A0.9300
O2—C31.376 (3)C14—H14A0.9300
O2—C231.411 (4)C15—C161.491 (4)
O3—C41.362 (3)C15—H15A0.9700
O3—C241.403 (4)C15—H15B0.9700
N1—C81.384 (3)C16—C171.363 (4)
N1—C71.386 (3)C16—C211.378 (4)
N1—C91.429 (3)C17—C181.363 (7)
N2—C71.294 (3)C18—C191.372 (8)
N2—N31.381 (3)C18—H18A0.9300
N3—C81.342 (3)C19—C201.319 (7)
N3—C151.461 (3)C19—H19A0.9300
C1—C61.384 (3)C20—C211.367 (6)
C1—C21.395 (3)C20—H20A0.9300
C1—H1A0.9300C22—H22A0.9600
C2—C31.386 (3)C22—H22B0.9600
C3—C41.381 (4)C22—H22C0.9600
C4—C51.395 (3)C23—H23A0.9600
C5—C61.387 (3)C23—H23B0.9600
C5—H5A0.9300C23—H23C0.9600
C6—C71.475 (3)C24—H24A0.9600
C9—C141.376 (3)C24—H24B0.9600
C9—C101.383 (3)C24—H24C0.9600
C10—C111.375 (4)
C2—O1—C22118.1 (2)C12—C13—H13A120.2
C3—O2—C23114.8 (2)C14—C13—H13A120.2
C4—O3—C24118.3 (2)C9—C14—C13119.4 (2)
C8—N1—C7107.74 (19)C9—C14—H14A120.3
C8—N1—C9122.63 (19)C13—C14—H14A120.3
C7—N1—C9129.08 (17)N3—C15—C16114.0 (2)
C7—N2—N3104.45 (19)N3—C15—H15A108.8
C8—N3—N2113.36 (18)C16—C15—H15A108.8
C8—N3—C15124.4 (2)N3—C15—H15B108.8
N2—N3—C15121.2 (2)C16—C15—H15B108.8
C6—C1—C2119.3 (2)H15A—C15—H15B107.7
C6—C1—H1A120.3C17—C16—C21113.4 (3)
C2—C1—H1A120.3C17—C16—C15123.5 (3)
O1—C2—C3115.9 (2)C21—C16—C15122.8 (3)
O1—C2—C1123.9 (2)F1—C17—C18119.2 (4)
C3—C2—C1120.2 (2)F1—C17—C16115.8 (4)
O2—C3—C4119.8 (2)C18—C17—C16124.9 (4)
O2—C3—C2119.9 (2)C17—C18—C19116.8 (4)
C4—C3—C2120.1 (2)C17—C18—H18A121.6
O3—C4—C3115.4 (2)C19—C18—H18A121.6
O3—C4—C5124.5 (2)C20—C19—C18122.5 (5)
C3—C4—C5120.1 (2)C20—C19—H19A118.7
C6—C5—C4119.5 (2)C18—C19—H19A118.7
C6—C5—H5A120.3C19—C20—C21117.8 (5)
C4—C5—H5A120.3C19—C20—H20A121.1
C1—C6—C5120.7 (2)C21—C20—H20A121.1
C1—C6—C7121.8 (2)F2—C21—C20119.1 (4)
C5—C6—C7117.5 (2)F2—C21—C16116.4 (3)
N2—C7—N1111.06 (19)C20—C21—C16124.5 (4)
N2—C7—C6123.4 (2)O1—C22—H22A109.5
N1—C7—C6125.6 (2)O1—C22—H22B109.5
N3—C8—N1103.31 (19)H22A—C22—H22B109.5
N3—C8—S1128.53 (17)O1—C22—H22C109.5
N1—C8—S1128.1 (2)H22A—C22—H22C109.5
C14—C9—C10120.7 (2)H22B—C22—H22C109.5
C14—C9—N1119.6 (2)O2—C23—H23A109.5
C10—C9—N1119.7 (2)O2—C23—H23B109.5
C11—C10—C9119.8 (2)H23A—C23—H23B109.5
C11—C10—H10A120.1O2—C23—H23C109.5
C9—C10—H10A120.1H23A—C23—H23C109.5
C10—C11—C12119.2 (2)H23B—C23—H23C109.5
C10—C11—H11A120.4O3—C24—H24A109.5
C12—C11—H11A120.4O3—C24—H24B109.5
C13—C12—C11121.2 (2)H24A—C24—H24B109.5
C13—C12—Br1119.0 (2)O3—C24—H24C109.5
C11—C12—Br1119.8 (2)H24A—C24—H24C109.5
C12—C13—C14119.6 (2)H24B—C24—H24C109.5
C7—N2—N3—C81.8 (3)C15—N3—C8—S15.6 (4)
C7—N2—N3—C15170.8 (3)C7—N1—C8—N32.5 (3)
C22—O1—C2—C3168.4 (3)C9—N1—C8—N3174.7 (2)
C22—O1—C2—C110.7 (4)C7—N1—C8—S1174.3 (2)
C6—C1—C2—O1178.1 (3)C9—N1—C8—S12.1 (4)
C6—C1—C2—C30.9 (4)C8—N1—C9—C14110.9 (3)
C23—O2—C3—C489.1 (3)C7—N1—C9—C1459.5 (3)
C23—O2—C3—C295.5 (3)C8—N1—C9—C1067.5 (3)
O1—C2—C3—O23.8 (4)C7—N1—C9—C10122.1 (3)
C1—C2—C3—O2175.3 (2)C14—C9—C10—C110.5 (4)
O1—C2—C3—C4179.2 (3)N1—C9—C10—C11178.0 (2)
C1—C2—C3—C40.0 (4)C9—C10—C11—C120.4 (4)
C24—O3—C4—C3177.9 (4)C10—C11—C12—C130.6 (5)
C24—O3—C4—C52.6 (6)C10—C11—C12—Br1178.9 (2)
O2—C3—C4—O35.4 (4)C11—C12—C13—C141.5 (4)
C2—C3—C4—O3179.2 (3)Br1—C12—C13—C14177.93 (19)
O2—C3—C4—C5174.1 (3)C10—C9—C14—C130.5 (4)
C2—C3—C4—C51.3 (5)N1—C9—C14—C13178.9 (2)
O3—C4—C5—C6179.0 (3)C12—C13—C14—C91.5 (4)
C3—C4—C5—C61.6 (5)C8—N3—C15—C16146.7 (3)
C2—C1—C6—C50.7 (4)N2—N3—C15—C1645.6 (4)
C2—C1—C6—C7177.9 (2)N3—C15—C16—C17106.4 (3)
C4—C5—C6—C10.6 (5)N3—C15—C16—C2178.7 (3)
C4—C5—C6—C7179.2 (3)C21—C16—C17—F1177.9 (3)
N3—N2—C7—N10.1 (3)C15—C16—C17—F12.5 (4)
N3—N2—C7—C6178.9 (2)C21—C16—C17—C180.4 (4)
C8—N1—C7—N21.6 (3)C15—C16—C17—C18175.8 (3)
C9—N1—C7—N2173.1 (2)F1—C17—C18—C19177.7 (4)
C8—N1—C7—C6177.2 (3)C16—C17—C18—C190.5 (6)
C9—N1—C7—C65.7 (4)C17—C18—C19—C200.1 (7)
C1—C6—C7—N2153.5 (3)C18—C19—C20—C210.3 (7)
C5—C6—C7—N227.9 (4)C19—C20—C21—F2178.6 (3)
C1—C6—C7—N127.9 (4)C19—C20—C21—C160.4 (6)
C5—C6—C7—N1150.7 (3)C17—C16—C21—F2178.9 (3)
N2—N3—C8—N12.7 (3)C15—C16—C21—F25.7 (4)
C15—N3—C8—N1171.3 (3)C17—C16—C21—C200.1 (4)
N2—N3—C8—S1174.1 (2)C15—C16—C21—C20175.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13A···O1i0.932.543.284 (3)137
C14—H14A···O2i0.932.403.142 (3)137
Symmetry code: (i) x, y, z+1/2.

Experimental details

Crystal data
Chemical formulaC24H20BrF2N3O3S
Mr548.40
Crystal system, space groupMonoclinic, C2/c
Temperature (K)296
a, b, c (Å)17.6694 (18), 15.5299 (16), 18.0855 (19)
β (°) 102.955 (2)
V3)4836.4 (9)
Z8
Radiation typeMo Kα
µ (mm1)1.83
Crystal size (mm)0.63 × 0.34 × 0.21
Data collection
DiffractometerBruker APEX DUO CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.391, 0.703
No. of measured, independent and
observed [I > 2σ(I)] reflections
20567, 7051, 3435
Rint0.041
(sin θ/λ)max1)0.705
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.158, 1.00
No. of reflections7051
No. of parameters310
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
C13—H13A···O1i0.932.543.284 (3)137
C14—H14A···O2i0.932.403.142 (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

First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science
First citationBruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationFun, 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
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals

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