4-(3-Chloro­phen­yl)-3-[(2,6-difluoro­benz­yl)sulfan­yl]-5-(3,4,5-trimeth­oxy­phen­yl)-4H-1,2,4-triazole

Fun, H.-K.; Asik, S.I.J.; Chandrakantha, B.; Isloor, A.M.; Shetty, P.

doi:10.1107/S1600536811048653

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Pages o3422-o3423

https://doi.org/10.1107/S1600536811048653

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4-(3-Chlorophenyl)-3-[(2,6-difluorobenzyl)sulfanyl]-5-(3,4,5-trimethoxyphenyl)-4H-1,2,4-triazole

Hoong-Kun Fun,^a ^*‡ Safra Izuani Jama Asik,^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 11 November 2011; accepted 16 November 2011; online 25 November 2011)

In the title compound, C₂₄H₂₀ClF₂N₃O₃S, the essentially planar triazole ring (r.m.s. deviation = 0.001 Å) forms dihedral angles of 22.35 (10), 68.17 (10) and 42.01 (10)° with the mean planes of the trimethoxyphenyl, chlorophenyl and difluorophenyl rings, respectively. A weak intramolecular C—H⋯π interaction occurs. In the crystal, molecules are linked into sheets lying parallel to the bc plane by C—H⋯O and C—H⋯N hydrogen bonds. The crystal packing also features weak C—H⋯π interactions.

Related literature

For the pharmacological activity of [1,2,4] triazole derivatives, see: Zhou et al. (2007 ); Chen et al. (2007 ); Isloor et al. (2010 ); Kalluraya et al. (2004 ); Sunil et al. (2009 ); Chandrakantha et al. (2010 ). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₄H₂₀ClF₂N₃O₃S
M_r = 503.94
Monoclinic, P 2₁ /c
a = 9.9867 (2) Å
b = 21.5140 (3) Å
c = 11.9793 (2) Å
β = 117.197 (1)°
V = 2289.24 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 100 K
0.36 × 0.17 × 0.11 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.896, T_max = 0.968
26235 measured reflections
6681 independent reflections
5130 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.110
S = 1.03
6681 reflections
310 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C1–C6 and C9–C14 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯O2ⁱ	0.95	2.43	3.353 (2)	165
C15—H15B⋯O3ⁱⁱ	0.99	2.54	3.281 (2)	132
C24—H24A⋯N2ⁱⁱⁱ	0.98	2.49	3.189 (2)	128
C20—H20A⋯Cg2^iv	0.95	2.66	3.543 (2)	154
C1—H1A⋯Cg3	0.95	2.85	3.6138 (19)	138
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) x, y, z+1; (iii) -x+2, -y+2, -z; (iv) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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: https://doi.org/10.1107/S1600536811048653/hb6503sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811048653/hb6503Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811048653/hb6503Isup3.cml

checkCIF report

Comment top

During the last few decades, a considerable attention has been devoted to the synthesis of [1, 2, 4] triazole derivatives possessing such diverse pharmacological properties as antimicrobial, anti-inflammatory (Zhou et al., 2007), analgesic antitumorial, antihypertensive (Chen et al., 2007), anticonvulsant and antiviral activities (Isloor et al., 2010). Some 1, 2, 4-triazoles are used as DNA cleaving agents and potassium channel activators. Introduction of fluorine atom in these compounds could alter the course of the pharmacological activities (Kalluraya et al., 2004). In particular, introduction of diflurophenyl substituted group in the moiety immensely increases the pharmacological as well liphophilicity effectiveness (Sunil et al., 2009). It is also observed that the amino and mercapto groups in triazoles are readily accessible nucleophilic centers (Chandrakantha et al., 2010).

In the title compound of (I), (Fig. 1), the triazole (N1–N3/C7/C8) ring is essentially planar, with maximum deviation of 0.001 Å for C1 and N2. The dihedral angles between triazole ring and the mean plane of trimethoxyphenyl (C1–C6/C22–C24/O1–O3), chlorophenyl (C9–C14/Cl1), and difluorophenyl groups (C16–C21/F1–F2) are 22.35 (10), 68.17 (10) and 42.01 (10)° respectively.

In the crystal structure of (Fig. 2), the molecules are linked into two-dimensional network parallel to bc plane by C11—H11A···O2, C15—H15B···O3 and C24—H24A···N2 hydrogen bonds. The crystal packing is further stabilized by weak C—H···π interactions (Table 1) with distances of 3.543 (2) and 3.6138 (19) A.

Related literature top

For the pharmacological activity of [1,2,4] triazole derivatives, see: Zhou et al. (2007); Chen et al. (2007); Isloor et al. (2010); Kalluraya et al. (2004); Sunil et al. (2009); Chandrakantha et al. (2010). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

To a solution of 4-(3-chloro phenyl)-5-(3,4,5-trimethoxy phenyl) -4H-1,2,4-triazole-3-thiol (1 g, 0.0026 mol) in dry acetonitrile (20 ml) was added potassium carbonate (0.73 g, 0.0053 mol) followed by 2,6-difluorobenzyl bromide (0.58 g, 0.0029 mol) at RT. After the addition, the reaction mixture was stirred at RT for 6h. Reaction mixture was monitored by TLC. After the completion, the reaction mixture was concentrated and purified by column chromatography using pet ether, ethyl acetate as an eluent to afford title compound as colorless solid. Yield: 1.1 g, 84%. M.p. 450-453 K.

Structure description top

For the pharmacological activity of [1,2,4] triazole derivatives, see: Zhou et al. (2007); Chen et al. (2007); Isloor et al. (2010); Kalluraya et al. (2004); Sunil et al. (2009); Chandrakantha et al. (2010). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

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 structure of the title compound, showing 50% probability displacement ellipsoids. Hydrogen atoms are shown as spheres of arbitrary radius.
	Fig. 2. The crystal packing, viewed along the a-axis, showing two-dimensional planes parallel to bc plane. Hydrogen atoms that not involved in hydrogen bonding (dashed lines) are omitted for clarity.

4-(3-Chlorophenyl)-3-[(2,6-difluorobenzyl)sulfanyl]-5-(3,4,5- trimethoxyphenyl)-4H-1,2,4-triazole top

Crystal data top

C₂₄H₂₀ClF₂N₃O₃S	F(000) = 1040
M_r = 503.94	D_x = 1.462 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7706 reflections
a = 9.9867 (2) Å	θ = 2.3–30.0°
b = 21.5140 (3) Å	µ = 0.31 mm⁻¹
c = 11.9793 (2) Å	T = 100 K
β = 117.197 (1)°	Block, colourless
V = 2289.24 (7) Å³	0.36 × 0.17 × 0.11 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	6681 independent reflections
Radiation source: fine-focus sealed tube	5130 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
φ and ω scans	θ_max = 30.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→14
T_min = 0.896, T_max = 0.968	k = −30→28
26235 measured reflections	l = −16→13

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.110	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0429P)² + 1.4878P] where P = (F_o² + 2F_c²)/3
6681 reflections	(Δ/σ)_max < 0.001
310 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₂₄H₂₀ClF₂N₃O₃S	V = 2289.24 (7) Å³
M_r = 503.94	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.9867 (2) Å	µ = 0.31 mm⁻¹
b = 21.5140 (3) Å	T = 100 K
c = 11.9793 (2) Å	0.36 × 0.17 × 0.11 mm
β = 117.197 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	6681 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	5130 reflections with I > 2σ(I)
T_min = 0.896, T_max = 0.968	R_int = 0.039
26235 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.110	H-atom parameters constrained
S = 1.03	Δρ_max = 0.43 e Å⁻³
6681 reflections	Δρ_min = −0.33 e Å⁻³
310 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Cl1	0.09590 (5)	0.86248 (3)	0.08433 (5)	0.03151 (13)
S1	0.68053 (5)	0.94142 (2)	0.38418 (4)	0.01701 (10)
F1	1.00621 (13)	0.87358 (6)	0.32771 (11)	0.0301 (3)
F2	0.68850 (14)	0.78856 (5)	0.47897 (11)	0.0313 (3)
O1	0.29452 (13)	0.86279 (6)	−0.34883 (11)	0.0175 (3)
O2	0.48997 (14)	0.88263 (6)	−0.44702 (11)	0.0175 (3)
O3	0.75145 (14)	0.93893 (6)	−0.31485 (11)	0.0182 (3)
N1	0.77291 (16)	0.99061 (7)	0.11532 (13)	0.0162 (3)
N2	0.79349 (16)	0.99452 (7)	0.23776 (13)	0.0163 (3)
N3	0.61625 (16)	0.92492 (6)	0.13604 (13)	0.0137 (3)
C1	0.47268 (19)	0.90647 (8)	−0.14903 (15)	0.0147 (3)
H1A	0.4059	0.8999	−0.1136	0.018*
C2	0.42908 (18)	0.89043 (8)	−0.27358 (15)	0.0146 (3)
C3	0.52434 (19)	0.90190 (8)	−0.32781 (15)	0.0139 (3)
C4	0.66518 (19)	0.92956 (8)	−0.25484 (15)	0.0143 (3)
C5	0.71188 (18)	0.94367 (8)	−0.12895 (15)	0.0146 (3)
H5A	0.8088	0.9609	−0.0791	0.018*
C6	0.61431 (19)	0.93212 (8)	−0.07673 (15)	0.0136 (3)
C7	0.66734 (18)	0.94915 (8)	0.05602 (15)	0.0137 (3)
C8	0.69995 (18)	0.95528 (8)	0.24881 (15)	0.0143 (3)
C9	0.50775 (19)	0.87636 (8)	0.11320 (14)	0.0139 (3)
C10	0.5402 (2)	0.81642 (8)	0.09147 (16)	0.0180 (3)
H10A	0.6346	0.8069	0.0944	0.022*
C11	0.4324 (2)	0.77023 (9)	0.06527 (16)	0.0216 (4)
H11A	0.4528	0.7289	0.0494	0.026*
C12	0.2952 (2)	0.78418 (9)	0.06222 (17)	0.0223 (4)
H12A	0.2215	0.7527	0.0442	0.027*
C13	0.2666 (2)	0.84463 (9)	0.08571 (16)	0.0196 (4)
C14	0.37204 (19)	0.89165 (8)	0.11156 (15)	0.0156 (3)
H14A	0.3518	0.9329	0.1276	0.019*
C15	0.8492 (2)	0.89379 (8)	0.47096 (16)	0.0180 (4)
H15A	0.9389	0.9180	0.4825	0.022*
H15B	0.8586	0.8847	0.5553	0.022*
C16	0.84819 (19)	0.83360 (8)	0.40752 (15)	0.0174 (3)
C17	0.9269 (2)	0.82486 (9)	0.33895 (16)	0.0201 (4)
C18	0.9289 (2)	0.76939 (9)	0.28106 (17)	0.0251 (4)
H18A	0.9852	0.7655	0.2354	0.030*
C19	0.8471 (2)	0.71991 (9)	0.29131 (18)	0.0270 (4)
H19A	0.8467	0.6815	0.2521	0.032*
C20	0.7655 (2)	0.72574 (9)	0.35825 (17)	0.0256 (4)
H20A	0.7092	0.6918	0.3657	0.031*
C21	0.7685 (2)	0.78214 (9)	0.41376 (16)	0.0208 (4)
C22	0.2031 (2)	0.84505 (9)	−0.29081 (17)	0.0204 (4)
H22A	0.1137	0.8230	−0.3518	0.031*
H22B	0.1720	0.8823	−0.2616	0.031*
H22C	0.2609	0.8178	−0.2193	0.031*
C23	0.3695 (2)	0.91553 (10)	−0.54687 (16)	0.0236 (4)
H23A	0.3463	0.8955	−0.6272	0.035*
H23B	0.4001	0.9587	−0.5485	0.035*
H23C	0.2801	0.9148	−0.5331	0.035*
C24	0.8921 (2)	0.97061 (9)	−0.24538 (18)	0.0237 (4)
H24A	0.9396	0.9779	−0.2999	0.036*
H24B	0.9586	0.9450	−0.1737	0.036*
H24C	0.8740	1.0105	−0.2151	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0222 (2)	0.0397 (3)	0.0385 (3)	−0.0091 (2)	0.0190 (2)	−0.0078 (2)
S1	0.0213 (2)	0.0192 (2)	0.01326 (19)	0.00148 (17)	0.01018 (16)	−0.00077 (16)
F1	0.0286 (6)	0.0313 (7)	0.0378 (7)	−0.0063 (5)	0.0217 (5)	−0.0054 (5)
F2	0.0480 (8)	0.0257 (6)	0.0333 (6)	−0.0054 (5)	0.0299 (6)	−0.0001 (5)
O1	0.0166 (6)	0.0213 (7)	0.0138 (6)	−0.0053 (5)	0.0063 (5)	−0.0016 (5)
O2	0.0221 (6)	0.0185 (6)	0.0120 (5)	0.0011 (5)	0.0080 (5)	−0.0016 (5)
O3	0.0198 (6)	0.0215 (6)	0.0170 (6)	−0.0054 (5)	0.0115 (5)	−0.0030 (5)
N1	0.0173 (7)	0.0187 (8)	0.0126 (7)	−0.0025 (6)	0.0068 (6)	−0.0017 (5)
N2	0.0183 (7)	0.0172 (7)	0.0131 (6)	−0.0016 (6)	0.0070 (6)	−0.0012 (5)
N3	0.0149 (6)	0.0134 (7)	0.0129 (6)	−0.0018 (5)	0.0064 (5)	−0.0013 (5)
C1	0.0160 (8)	0.0144 (8)	0.0136 (7)	0.0010 (6)	0.0066 (6)	0.0020 (6)
C2	0.0147 (8)	0.0132 (8)	0.0139 (8)	0.0007 (6)	0.0048 (6)	0.0015 (6)
C3	0.0176 (8)	0.0125 (8)	0.0109 (7)	0.0010 (6)	0.0060 (6)	−0.0002 (6)
C4	0.0164 (8)	0.0145 (8)	0.0143 (8)	−0.0001 (6)	0.0091 (6)	0.0016 (6)
C5	0.0152 (8)	0.0130 (8)	0.0148 (8)	−0.0012 (6)	0.0061 (6)	−0.0001 (6)
C6	0.0159 (7)	0.0120 (8)	0.0121 (7)	0.0013 (6)	0.0057 (6)	0.0015 (6)
C7	0.0153 (7)	0.0146 (8)	0.0122 (7)	0.0012 (6)	0.0070 (6)	0.0010 (6)
C8	0.0165 (8)	0.0146 (8)	0.0120 (7)	0.0018 (6)	0.0068 (6)	−0.0004 (6)
C9	0.0169 (8)	0.0148 (8)	0.0092 (7)	−0.0024 (6)	0.0053 (6)	0.0012 (6)
C10	0.0200 (8)	0.0157 (8)	0.0161 (8)	0.0013 (7)	0.0066 (7)	0.0005 (7)
C11	0.0283 (10)	0.0138 (8)	0.0188 (8)	−0.0022 (7)	0.0074 (7)	0.0004 (7)
C12	0.0261 (9)	0.0193 (9)	0.0190 (9)	−0.0098 (7)	0.0082 (7)	0.0005 (7)
C13	0.0194 (8)	0.0248 (10)	0.0157 (8)	−0.0039 (7)	0.0091 (7)	0.0001 (7)
C14	0.0189 (8)	0.0155 (8)	0.0135 (8)	−0.0013 (6)	0.0084 (6)	−0.0003 (6)
C15	0.0219 (9)	0.0170 (9)	0.0122 (8)	0.0002 (7)	0.0052 (7)	−0.0004 (6)
C16	0.0190 (8)	0.0162 (8)	0.0125 (8)	0.0018 (7)	0.0034 (6)	0.0006 (6)
C17	0.0185 (8)	0.0215 (9)	0.0184 (8)	−0.0004 (7)	0.0068 (7)	0.0001 (7)
C18	0.0259 (10)	0.0288 (11)	0.0206 (9)	0.0078 (8)	0.0105 (8)	−0.0015 (8)
C19	0.0343 (11)	0.0197 (10)	0.0210 (9)	0.0074 (8)	0.0075 (8)	−0.0015 (7)
C20	0.0332 (11)	0.0176 (9)	0.0217 (9)	0.0011 (8)	0.0087 (8)	0.0032 (7)
C21	0.0285 (10)	0.0198 (9)	0.0160 (8)	0.0023 (7)	0.0118 (7)	0.0030 (7)
C22	0.0168 (8)	0.0252 (10)	0.0196 (9)	−0.0050 (7)	0.0087 (7)	−0.0011 (7)
C23	0.0211 (9)	0.0335 (11)	0.0142 (8)	0.0018 (8)	0.0065 (7)	0.0021 (7)
C24	0.0233 (9)	0.0285 (10)	0.0242 (9)	−0.0108 (8)	0.0151 (8)	−0.0085 (8)

Geometric parameters (Å, º) top

Cl1—C13	1.7404 (19)	C10—H10A	0.9500
S1—C8	1.7446 (17)	C11—C12	1.386 (3)
S1—C15	1.8352 (18)	C11—H11A	0.9500
F1—C17	1.357 (2)	C12—C13	1.388 (3)
F2—C21	1.355 (2)	C12—H12A	0.9500
O1—C2	1.366 (2)	C13—C14	1.389 (2)
O1—C22	1.429 (2)	C14—H14A	0.9500
O2—C3	1.3714 (19)	C15—C16	1.499 (2)
O2—C23	1.436 (2)	C15—H15A	0.9900
O3—C4	1.366 (2)	C15—H15B	0.9900
O3—C24	1.436 (2)	C16—C17	1.385 (3)
N1—C7	1.314 (2)	C16—C21	1.386 (3)
N1—N2	1.3875 (19)	C17—C18	1.385 (3)
N2—C8	1.310 (2)	C18—C19	1.381 (3)
N3—C7	1.378 (2)	C18—H18A	0.9500
N3—C8	1.385 (2)	C19—C20	1.385 (3)
N3—C9	1.439 (2)	C19—H19A	0.9500
C1—C6	1.391 (2)	C20—C21	1.377 (3)
C1—C2	1.393 (2)	C20—H20A	0.9500
C1—H1A	0.9500	C22—H22A	0.9800
C2—C3	1.397 (2)	C22—H22B	0.9800
C3—C4	1.405 (2)	C22—H22C	0.9800
C4—C5	1.393 (2)	C23—H23A	0.9800
C5—C6	1.400 (2)	C23—H23B	0.9800
C5—H5A	0.9500	C23—H23C	0.9800
C6—C7	1.474 (2)	C24—H24A	0.9800
C9—C10	1.383 (2)	C24—H24B	0.9800
C9—C14	1.386 (2)	C24—H24C	0.9800
C10—C11	1.392 (3)

C8—S1—C15	99.14 (8)	C14—C13—Cl1	118.74 (14)
C2—O1—C22	116.74 (13)	C9—C14—C13	117.84 (16)
C3—O2—C23	115.73 (13)	C9—C14—H14A	121.1
C4—O3—C24	116.76 (13)	C13—C14—H14A	121.1
C7—N1—N2	107.89 (13)	C16—C15—S1	113.79 (12)
C8—N2—N1	107.45 (13)	C16—C15—H15A	108.8
C7—N3—C8	104.48 (13)	S1—C15—H15A	108.8
C7—N3—C9	128.96 (14)	C16—C15—H15B	108.8
C8—N3—C9	126.46 (14)	S1—C15—H15B	108.8
C6—C1—C2	119.75 (15)	H15A—C15—H15B	107.7
C6—C1—H1A	120.1	C17—C16—C21	114.80 (16)
C2—C1—H1A	120.1	C17—C16—C15	122.94 (16)
O1—C2—C1	123.12 (15)	C21—C16—C15	122.26 (16)
O1—C2—C3	116.34 (14)	F1—C17—C18	118.26 (17)
C1—C2—C3	120.54 (15)	F1—C17—C16	117.97 (16)
O2—C3—C2	122.08 (15)	C18—C17—C16	123.77 (18)
O2—C3—C4	118.62 (15)	C19—C18—C17	118.37 (18)
C2—C3—C4	119.10 (15)	C19—C18—H18A	120.8
O3—C4—C5	123.91 (15)	C17—C18—H18A	120.8
O3—C4—C3	115.34 (14)	C18—C19—C20	120.65 (18)
C5—C4—C3	120.70 (15)	C18—C19—H19A	119.7
C4—C5—C6	119.21 (15)	C20—C19—H19A	119.7
C4—C5—H5A	120.4	C21—C20—C19	118.10 (18)
C6—C5—H5A	120.4	C21—C20—H20A	121.0
C1—C6—C5	120.63 (15)	C19—C20—H20A	121.0
C1—C6—C7	122.13 (15)	F2—C21—C20	118.68 (17)
C5—C6—C7	117.23 (15)	F2—C21—C16	117.01 (16)
N1—C7—N3	109.96 (14)	C20—C21—C16	124.31 (18)
N1—C7—C6	123.75 (15)	O1—C22—H22A	109.5
N3—C7—C6	126.29 (15)	O1—C22—H22B	109.5
N2—C8—N3	110.22 (14)	H22A—C22—H22B	109.5
N2—C8—S1	126.26 (13)	O1—C22—H22C	109.5
N3—C8—S1	123.52 (13)	H22A—C22—H22C	109.5
C10—C9—C14	122.02 (16)	H22B—C22—H22C	109.5
C10—C9—N3	119.47 (15)	O2—C23—H23A	109.5
C14—C9—N3	118.49 (15)	O2—C23—H23B	109.5
C9—C10—C11	118.98 (17)	H23A—C23—H23B	109.5
C9—C10—H10A	120.5	O2—C23—H23C	109.5
C11—C10—H10A	120.5	H23A—C23—H23C	109.5
C12—C11—C10	120.31 (17)	H23B—C23—H23C	109.5
C12—C11—H11A	119.8	O3—C24—H24A	109.5
C10—C11—H11A	119.8	O3—C24—H24B	109.5
C11—C12—C13	119.34 (17)	H24A—C24—H24B	109.5
C11—C12—H12A	120.3	O3—C24—H24C	109.5
C13—C12—H12A	120.3	H24A—C24—H24C	109.5
C12—C13—C14	121.50 (17)	H24B—C24—H24C	109.5
C12—C13—Cl1	119.76 (14)

C7—N1—N2—C8	0.07 (18)	C9—N3—C8—N2	176.61 (15)
C22—O1—C2—C1	−5.8 (2)	C7—N3—C8—S1	−179.61 (12)
C22—O1—C2—C3	173.75 (15)	C9—N3—C8—S1	−3.0 (2)
C6—C1—C2—O1	177.28 (15)	C15—S1—C8—N2	−76.25 (16)
C6—C1—C2—C3	−2.3 (2)	C15—S1—C8—N3	103.35 (15)
C23—O2—C3—C2	71.3 (2)	C7—N3—C9—C10	65.5 (2)
C23—O2—C3—C4	−113.93 (18)	C8—N3—C9—C10	−110.22 (19)
O1—C2—C3—O2	−4.5 (2)	C7—N3—C9—C14	−113.38 (19)
C1—C2—C3—O2	175.11 (15)	C8—N3—C9—C14	70.9 (2)
O1—C2—C3—C4	−179.25 (15)	C14—C9—C10—C11	1.0 (2)
C1—C2—C3—C4	0.3 (2)	N3—C9—C10—C11	−177.84 (15)
C24—O3—C4—C5	−6.1 (2)	C9—C10—C11—C12	−0.6 (3)
C24—O3—C4—C3	176.26 (15)	C10—C11—C12—C13	−0.1 (3)
O2—C3—C4—O3	4.8 (2)	C11—C12—C13—C14	0.4 (3)
C2—C3—C4—O3	179.76 (15)	C11—C12—C13—Cl1	−179.09 (14)
O2—C3—C4—C5	−172.94 (15)	C10—C9—C14—C13	−0.7 (2)
C2—C3—C4—C5	2.0 (2)	N3—C9—C14—C13	178.12 (14)
O3—C4—C5—C6	−179.94 (15)	C12—C13—C14—C9	0.0 (3)
C3—C4—C5—C6	−2.4 (2)	Cl1—C13—C14—C9	179.49 (12)
C2—C1—C6—C5	1.9 (2)	C8—S1—C15—C16	−63.03 (14)
C2—C1—C6—C7	−179.10 (15)	S1—C15—C16—C17	100.76 (18)
C4—C5—C6—C1	0.4 (2)	S1—C15—C16—C21	−79.58 (19)
C4—C5—C6—C7	−178.63 (15)	C21—C16—C17—F1	179.26 (15)
N2—N1—C7—N3	−0.04 (19)	C15—C16—C17—F1	−1.1 (3)
N2—N1—C7—C6	−179.95 (15)	C21—C16—C17—C18	−0.5 (3)
C8—N3—C7—N1	0.00 (18)	C15—C16—C17—C18	179.14 (17)
C9—N3—C7—N1	−176.45 (16)	F1—C17—C18—C19	−179.36 (16)
C8—N3—C7—C6	179.90 (16)	C16—C17—C18—C19	0.4 (3)
C9—N3—C7—C6	3.5 (3)	C17—C18—C19—C20	−0.2 (3)
C1—C6—C7—N1	−156.64 (17)	C18—C19—C20—C21	0.1 (3)
C5—C6—C7—N1	22.4 (2)	C19—C20—C21—F2	179.65 (17)
C1—C6—C7—N3	23.5 (3)	C19—C20—C21—C16	−0.2 (3)
C5—C6—C7—N3	−157.48 (16)	C17—C16—C21—F2	−179.45 (15)
N1—N2—C8—N3	−0.08 (19)	C15—C16—C21—F2	0.9 (3)
N1—N2—C8—S1	179.57 (12)	C17—C16—C21—C20	0.4 (3)
C7—N3—C8—N2	0.05 (18)	C15—C16—C21—C20	−179.24 (17)

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of the C1–C6 and C9–C14 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O2ⁱ	0.95	2.43	3.353 (2)	165
C15—H15B···O3ⁱⁱ	0.99	2.54	3.281 (2)	132
C24—H24A···N2ⁱⁱⁱ	0.98	2.49	3.189 (2)	128
C20—H20A···Cg2^iv	0.95	2.66	3.543 (2)	154
C1—H1A···Cg3	0.95	2.85	3.6138 (19)	138

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x, y, z+1; (iii) −x+2, −y+2, −z; (iv) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₀ClF₂N₃O₃S
M_r	503.94
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	9.9867 (2), 21.5140 (3), 11.9793 (2)
β (°)	117.197 (1)
V (Å³)	2289.24 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.36 × 0.17 × 0.11

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.896, 0.968
No. of measured, independent and observed [I > 2σ(I)] reflections	26235, 6681, 5130
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.704

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.110, 1.03
No. of reflections	6681
No. of parameters	310
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.33

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

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of the C1–C6 and C9–C14 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O2ⁱ	0.95	2.43	3.353 (2)	165
C15—H15B···O3ⁱⁱ	0.99	2.54	3.281 (2)	132
C24—H24A···N2ⁱⁱⁱ	0.98	2.49	3.189 (2)	128
C20—H20A···Cg2^iv	0.95	2.66	3.543 (2)	154
C1—H1A···Cg3	0.95	2.85	3.6138 (19)	138

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x, y, z+1; (iii) −x+2, −y+2, −z; (iv) x, −y+1/2, z−1/2.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and SIJA thank the Malaysian Government and Universiti Sains Malaysia for the Research University Grants (Nos.1001/PFIZIK/811160 and 1001/PFIZIK/ 811151). AMI thanks the Board for Research in Nuclear Sciences, Department of Atomic Energy, and the Government of India for the Young Scientist award.

References

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Volume 67| Part 12| December 2011| Pages o3422-o3423

https://doi.org/10.1107/S1600536811048653

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

4-(3-Chloro­phen­yl)-3-[(2,6-di­fluoro­benz­yl)sulfan­yl]-5-(3,4,5-trimeth­­oxy­phen­yl)-4H-1,2,4-triazole

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

4-(3-Chlorophenyl)-3-[(2,6-difluorobenzyl)sulfanyl]-5-(3,4,5-trimethoxyphenyl)-4H-1,2,4-triazole