N,N-Bis(2,6-difluoro­benz­yl)-1,3,4-thia­diazol-2-amine

Fun, H.-K.; Liew, W.-C.; Chandrakantha, B.; Isloor, A.M.

doi:10.1107/S1600536809031675

organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Pages o2166-o2167

doi:10.1107/S1600536809031675

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N,N-Bis(2,6-difluorobenzyl)-1,3,4-thiadiazol-2-amine

Hoong-Kun Fun,^a ^*‡ Wei-Ching Liew,^a B. Chandrakantha ^b and Arun M. Isloor ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bSyngene International Ltd, Biocon Park, Plot Nos. 2 & 3, Bommasandra 4th Phase, Jigani Link Rd, Bangalore 560 100, India, and ^cDepartment of Chemistry, National Institute of Technology-Karnataka, Surathkal, Mangalore 575 025, India
^*Correspondence e-mail: hkfun@usm.my

(Received 11 August 2009; accepted 11 August 2009; online 15 August 2009)

In the title compound, C₁₆H₁₁F₄N₃S, the dihedral angles between the thiadiazole ring and the difluorobenzyl rings are 81.95 (7) and 81.96 (7)°, whereas the dihedral angle between the difluorobenzyl rings is 11.41 (7)°. In the crystal structure, C—H⋯N and C—H⋯F interactions link the molecules into two-dimensional arrays parallel to the bc plane.

Related literature

For the synthesis of pharmaceutically condensed heterocyclic thiadiazole derivatives as antimicrobials, see: Swamy et al. (2006 ). For the synthesis and anti-inflammatory, analgesic, ulcerogenic and lipid peroxidation activity of some new acetic acid derivatives, see: Amir & Shikha (2004 ). For new bis-aminomercaptotriazoles and bis-triazolothiadiazoles as possible anticancer agents, see: Holla et al. (2002 ). For the synthesis and biological evaluation of thiadiazole derivatives as a novel class of potential anti-tumor agents, see: Ibrahim (2009 ). For related structures, see: Wang et al. (2009a ,b ); Yin et al. (2008 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₆H₁₁F₄N₃S
M_r = 353.34
Orthorhombic, P c a 2₁
a = 32.6678 (6) Å
b = 5.8515 (1) Å
c = 7.8140 (2) Å
V = 1493.69 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 100 K
0.46 × 0.33 × 0.14 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.887, T_max = 0.965
17980 measured reflections
4796 independent reflections
4299 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.076
S = 1.02
4796 reflections
218 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.26 e Å⁻³
Absolute structure: Flack (1983 ), 1935 Friedel pairs
Flack parameter: 0.20 (5)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯N1ⁱ	0.93	2.58	3.392 (2)	146
C3—H3B⋯F3ⁱⁱ	0.97	2.47	3.0226 (16)	116
C8—H8A⋯F4ⁱⁱⁱ	0.93	2.54	3.144 (2)	123
C10—H10B⋯N2^iv	0.97	2.56	3.4191 (17)	148
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y, z-{\script{1\over 2}}]$ ; (ii) x, y+1, z; (iii) x, y-1, z+1; (iv) x, y-1, z.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); 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/S1600536809031675/tk2527sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809031675/tk2527Isup2.hkl

checkCIF report

Comment top

Heterocycles bearing 1,3,4-thiadiazole moieties represent an interesting class of compounds possessing a wide spectrum of biological activity (Swamy et al., 2006) such as anti-inflammatory, anti-viral and anti-microbial properties (Amir & Shikha, 2004). Recently, 1,3,4-thiadiazoles have attracted particular attention due to their analgesic, ulcerogenic and lipidperoxidation activities (Holla et al., 2002). In particular, the derivatives of variously substituted 1,3,4-thiadiazoles are also known to exhibit anti-depressant and anxiolitic agents (Ibrahim, 2009). Herein, the crystal structure of the title compound (I) is reported.

In (I), Fig. 1, the bond lengths and angles are comparable to related structures (Wang et al., 2009a & b; Yin et al., 2008). The dihedral angles between the thiadiazole ring (C1—C2/S1/N1—N2) and the difluorobenzyl rings [(C4—C9) and (C11—C16)] are 81.95 (7)° and 81.86 (7)°, respectively whereas the dihedral angle between the difluorobenzyl rings is 11.41 (7)°. These data indicate that all the three rings are twisted from each other.

The crystal packing (Fig. 2) is consolidated by C—H···N and C—H···F interactions (Table 1) that link molecules into two-dimensional arrays parallel to the bc plane.

Related literature top

For the synthesis of pharmaceutically condensed heterocyclic thiadiazole derivatives as antimicrobials, see: Swamy et al. (2006). For the synthesis and anti-inflammatory, analgesic, ulcerogenic and lipid peroxidation activity of some new acetic acid derivatives, see: Amir & Shikha (2004). For new bis-aminomercaptotriazoles and bis-triazolothiadiazoles as possible anticancer agents, see: Holla et al. (2002). For the synthesis and biological evaluation of thiadiazole derivatives as a novel class of potential anti-tumor agents, see: Ibrahim (2009). For related structures, see: Wang et al. (2009a,b); Yin et al. (2008). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

Anhydrous potassium carbonate (5.4 g, 0.0395 mol) was added to a solution of 1,3,4-thiadiazole-2-amine (2 g, 0.0197 mol) in dry acetonitrile (25 ml). The reaction mixture was stirred for 15 min. 2,6-Difluorobenzyl bromide (8.18 g, 0.0395 mol) was added drop-wise to the mixture. After addition, the reaction mixture was stirred at room temperature for 18 h, filtered, and the filtrate was concentrated. The crude product was purified by column chromatography using 60–120 silica gel. The fraction eluted with 10% ethyl acetate in hexane was concentrated to produce (I) as a pale-yellow crystalline solid. Yield 5.0 g, 71.63%. m.p. 421–423 K.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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 (I), showing 50% probability displacement ellipsoids and the atom numbering scheme.
	Fig. 2. Crystal packing viewed along the b-axis. C-H···N and C-H···F interactions are shown as dashed lines.

N,N-Bis(2,6-difluorobenzyl)-1,3,4-thiadiazol-2-amine top

Crystal data top

C₁₆H₁₁F₄N₃S	F(000) = 720
M_r = 353.34	D_x = 1.571 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 9387 reflections
a = 32.6678 (6) Å	θ = 2.9–33.7°
b = 5.8515 (1) Å	µ = 0.26 mm⁻¹
c = 7.8140 (2) Å	T = 100 K
V = 1493.69 (5) Å³	Block, pale-yellow
Z = 4	0.46 × 0.33 × 0.14 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4796 independent reflections
Radiation source: fine-focus sealed tube	4299 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ϕ and ω scans	θ_max = 32.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −48→46
T_min = 0.887, T_max = 0.965	k = −8→8
17980 measured reflections	l = −11→11

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.033	H-atom parameters constrained
wR(F²) = 0.076	w = 1/[σ²(F_o²) + (0.0345P)² + 0.2893P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
4796 reflections	Δρ_max = 0.23 e Å⁻³
218 parameters	Δρ_min = −0.26 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1935 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.20 (5)

Crystal data top

C₁₆H₁₁F₄N₃S	V = 1493.69 (5) Å³
M_r = 353.34	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 32.6678 (6) Å	µ = 0.26 mm⁻¹
b = 5.8515 (1) Å	T = 100 K
c = 7.8140 (2) Å	0.46 × 0.33 × 0.14 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4796 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	4299 reflections with I > 2σ(I)
T_min = 0.887, T_max = 0.965	R_int = 0.027
17980 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	H-atom parameters constrained
wR(F²) = 0.076	Δρ_max = 0.23 e Å⁻³
S = 1.02	Δρ_min = −0.26 e Å⁻³
4796 reflections	Absolute structure: Flack (1983), 1935 Friedel pairs
218 parameters	Absolute structure parameter: 0.20 (5)
1 restraint

Special details top

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

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
S1	0.794704 (10)	0.52906 (6)	−0.01577 (5)	0.02346 (8)
F1	0.79830 (2)	0.37874 (17)	0.48808 (16)	0.0338 (2)
F2	0.94005 (2)	0.27091 (16)	0.53340 (11)	0.0261 (2)
F3	0.92412 (3)	−0.07230 (15)	0.24104 (14)	0.0264 (2)
F4	0.91204 (3)	0.60294 (17)	−0.07755 (14)	0.0338 (2)
N1	0.78098 (4)	0.8994 (2)	0.14916 (18)	0.0236 (3)
N2	0.81456 (4)	0.8012 (2)	0.22916 (17)	0.0209 (2)
N3	0.85771 (4)	0.4805 (2)	0.21110 (16)	0.0190 (2)
C1	0.76794 (4)	0.7789 (3)	0.0214 (2)	0.0249 (3)
H1A	0.7458	0.8235	−0.0455	0.030*
C2	0.82545 (4)	0.6085 (2)	0.15657 (18)	0.0160 (2)
C3	0.87577 (4)	0.5273 (2)	0.3784 (2)	0.0187 (3)
H3A	0.8637	0.6655	0.4249	0.022*
H3B	0.9049	0.5537	0.3647	0.022*
C4	0.86929 (4)	0.3330 (2)	0.50333 (18)	0.0162 (2)
C5	0.83046 (4)	0.2629 (3)	0.5541 (2)	0.0213 (3)
C6	0.82293 (5)	0.0864 (3)	0.6657 (2)	0.0242 (3)
H6A	0.7963	0.0468	0.6955	0.029*
C7	0.85629 (5)	−0.0312 (3)	0.7328 (2)	0.0238 (3)
H7A	0.8520	−0.1523	0.8078	0.029*
C8	0.89596 (5)	0.0308 (3)	0.68863 (19)	0.0220 (3)
H8A	0.9184	−0.0466	0.7334	0.026*
C9	0.90109 (4)	0.2105 (2)	0.57631 (19)	0.0181 (3)
C10	0.87024 (4)	0.2743 (2)	0.1207 (2)	0.0194 (3)
H10A	0.8557	0.2656	0.0126	0.023*
H10B	0.8627	0.1417	0.1882	0.023*
C11	0.91598 (4)	0.2685 (2)	0.08670 (19)	0.0175 (3)
C12	0.94120 (4)	0.0961 (2)	0.14585 (18)	0.0184 (3)
C13	0.98273 (5)	0.0831 (3)	0.1130 (2)	0.0234 (3)
H13A	0.9984	−0.0374	0.1548	0.028*
C14	1.00032 (4)	0.2553 (3)	0.0158 (2)	0.0260 (3)
H14A	1.0282	0.2512	−0.0072	0.031*
C15	0.97688 (5)	0.4331 (3)	−0.0475 (2)	0.0272 (3)
H15A	0.9886	0.5489	−0.1125	0.033*
C16	0.93555 (4)	0.4336 (2)	−0.0113 (2)	0.0218 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01673 (15)	0.03179 (18)	0.02187 (15)	0.00300 (13)	−0.00547 (14)	−0.00224 (18)
F1	0.0139 (4)	0.0423 (5)	0.0451 (5)	0.0051 (4)	−0.0022 (4)	0.0137 (6)
F2	0.0124 (4)	0.0360 (5)	0.0298 (5)	0.0007 (3)	−0.0012 (3)	0.0101 (4)
F3	0.0237 (4)	0.0208 (4)	0.0345 (5)	0.0013 (3)	0.0037 (4)	0.0108 (4)
F4	0.0341 (5)	0.0282 (5)	0.0390 (5)	0.0040 (4)	−0.0034 (4)	0.0175 (4)
N1	0.0206 (6)	0.0248 (6)	0.0253 (6)	0.0062 (5)	−0.0010 (5)	0.0065 (5)
N2	0.0187 (6)	0.0213 (6)	0.0226 (6)	0.0044 (4)	−0.0020 (5)	0.0032 (5)
N3	0.0181 (5)	0.0192 (5)	0.0196 (5)	0.0039 (4)	−0.0049 (4)	−0.0013 (5)
C1	0.0165 (6)	0.0339 (8)	0.0243 (7)	0.0059 (6)	−0.0018 (5)	0.0044 (6)
C2	0.0127 (6)	0.0192 (6)	0.0161 (5)	−0.0015 (5)	−0.0012 (4)	0.0041 (5)
C3	0.0192 (6)	0.0172 (6)	0.0198 (6)	−0.0007 (5)	−0.0054 (5)	0.0006 (5)
C4	0.0132 (5)	0.0177 (6)	0.0177 (6)	0.0003 (4)	−0.0022 (5)	0.0000 (5)
C5	0.0150 (6)	0.0230 (7)	0.0258 (7)	0.0015 (5)	−0.0015 (5)	0.0003 (6)
C6	0.0199 (7)	0.0277 (8)	0.0250 (7)	−0.0054 (6)	0.0019 (5)	0.0003 (6)
C7	0.0296 (8)	0.0218 (7)	0.0200 (7)	−0.0022 (6)	0.0024 (6)	0.0032 (6)
C8	0.0220 (7)	0.0233 (7)	0.0206 (7)	0.0039 (6)	−0.0031 (5)	0.0030 (6)
C9	0.0141 (6)	0.0208 (6)	0.0193 (6)	−0.0005 (5)	−0.0004 (5)	0.0001 (5)
C10	0.0167 (6)	0.0180 (6)	0.0235 (7)	0.0011 (5)	−0.0027 (5)	−0.0023 (6)
C11	0.0167 (6)	0.0176 (6)	0.0181 (6)	0.0001 (5)	−0.0012 (5)	0.0001 (5)
C12	0.0203 (6)	0.0164 (6)	0.0185 (6)	−0.0009 (5)	0.0014 (5)	0.0005 (5)
C13	0.0201 (7)	0.0243 (7)	0.0259 (7)	0.0049 (5)	0.0009 (5)	−0.0005 (6)
C14	0.0184 (6)	0.0345 (8)	0.0252 (8)	−0.0026 (6)	0.0044 (5)	−0.0024 (7)
C15	0.0278 (8)	0.0299 (8)	0.0238 (8)	−0.0075 (6)	0.0042 (6)	0.0053 (6)
C16	0.0252 (7)	0.0191 (6)	0.0211 (6)	0.0009 (5)	−0.0027 (6)	0.0058 (7)

Geometric parameters (Å, º) top

S1—C1	1.7278 (16)	C6—C7	1.392 (2)
S1—C2	1.7431 (14)	C6—H6A	0.9300
F1—C5	1.3527 (16)	C7—C8	1.389 (2)
F2—C9	1.3630 (15)	C7—H7A	0.9300
F3—C12	1.3548 (17)	C8—C9	1.380 (2)
F4—C16	1.3566 (16)	C8—H8A	0.9300
N1—C1	1.295 (2)	C10—C11	1.5179 (19)
N1—N2	1.3872 (16)	C10—H10A	0.9700
N2—C2	1.3114 (19)	C10—H10B	0.9700
N3—C2	1.3613 (17)	C11—C12	1.3824 (19)
N3—C10	1.4570 (18)	C11—C16	1.388 (2)
N3—C3	1.4598 (19)	C12—C13	1.383 (2)
C1—H1A	0.9300	C13—C14	1.387 (2)
C3—C4	1.514 (2)	C13—H13A	0.9300
C3—H3A	0.9700	C14—C15	1.383 (2)
C3—H3B	0.9700	C14—H14A	0.9300
C4—C9	1.3848 (18)	C15—C16	1.380 (2)
C4—C5	1.3906 (19)	C15—H15A	0.9300
C5—C6	1.374 (2)

C1—S1—C2	86.35 (7)	C9—C8—C7	118.05 (14)
C1—N1—N2	112.47 (13)	C9—C8—H8A	121.0
C2—N2—N1	112.07 (13)	C7—C8—H8A	121.0
C2—N3—C10	121.42 (12)	F2—C9—C8	117.87 (12)
C2—N3—C3	119.33 (12)	F2—C9—C4	117.72 (12)
C10—N3—C3	118.42 (11)	C8—C9—C4	124.41 (13)
N1—C1—S1	115.07 (11)	N3—C10—C11	112.32 (11)
N1—C1—H1A	122.5	N3—C10—H10A	109.1
S1—C1—H1A	122.5	C11—C10—H10A	109.1
N2—C2—N3	123.20 (13)	N3—C10—H10B	109.1
N2—C2—S1	114.03 (10)	C11—C10—H10B	109.1
N3—C2—S1	122.77 (11)	H10A—C10—H10B	107.9
N3—C3—C4	112.33 (11)	C12—C11—C16	114.68 (12)
N3—C3—H3A	109.1	C12—C11—C10	122.98 (12)
C4—C3—H3A	109.1	C16—C11—C10	122.31 (13)
N3—C3—H3B	109.1	F3—C12—C11	117.97 (12)
C4—C3—H3B	109.1	F3—C12—C13	117.77 (13)
H3A—C3—H3B	107.9	C11—C12—C13	124.25 (13)
C9—C4—C5	114.46 (13)	C12—C13—C14	117.94 (14)
C9—C4—C3	123.33 (11)	C12—C13—H13A	121.0
C5—C4—C3	122.21 (12)	C14—C13—H13A	121.0
F1—C5—C6	118.65 (13)	C15—C14—C13	120.85 (14)
F1—C5—C4	116.87 (13)	C15—C14—H14A	119.6
C6—C5—C4	124.48 (14)	C13—C14—H14A	119.6
C5—C6—C7	118.08 (14)	C16—C15—C14	118.03 (14)
C5—C6—H6A	121.0	C16—C15—H15A	121.0
C7—C6—H6A	121.0	C14—C15—H15A	121.0
C8—C7—C6	120.51 (14)	F4—C16—C15	118.49 (13)
C8—C7—H7A	119.7	F4—C16—C11	117.26 (12)
C6—C7—H7A	119.7	C15—C16—C11	124.24 (13)

C1—N1—N2—C2	0.11 (18)	C7—C8—C9—C4	−0.5 (2)
N2—N1—C1—S1	0.64 (17)	C5—C4—C9—F2	−179.53 (12)
C2—S1—C1—N1	−0.89 (12)	C3—C4—C9—F2	0.5 (2)
N1—N2—C2—N3	179.58 (13)	C5—C4—C9—C8	0.9 (2)
N1—N2—C2—S1	−0.80 (15)	C3—C4—C9—C8	−179.07 (14)
C10—N3—C2—N2	−176.38 (13)	C2—N3—C10—C11	131.34 (14)
C3—N3—C2—N2	14.2 (2)	C3—N3—C10—C11	−59.13 (17)
C10—N3—C2—S1	4.04 (19)	N3—C10—C11—C12	121.31 (15)
C3—N3—C2—S1	−165.40 (10)	N3—C10—C11—C16	−60.72 (19)
C1—S1—C2—N2	0.94 (11)	C16—C11—C12—F3	−179.37 (13)
C1—S1—C2—N3	−179.44 (13)	C10—C11—C12—F3	−1.3 (2)
C2—N3—C3—C4	113.44 (14)	C16—C11—C12—C13	0.1 (2)
C10—N3—C3—C4	−56.32 (16)	C10—C11—C12—C13	178.17 (14)
N3—C3—C4—C9	118.26 (15)	F3—C12—C13—C14	−179.93 (14)
N3—C3—C4—C5	−61.69 (18)	C11—C12—C13—C14	0.6 (2)
C9—C4—C5—F1	179.22 (13)	C12—C13—C14—C15	−0.6 (2)
C3—C4—C5—F1	−0.8 (2)	C13—C14—C15—C16	−0.1 (2)
C9—C4—C5—C6	−0.6 (2)	C14—C15—C16—F4	−177.79 (14)
C3—C4—C5—C6	179.38 (14)	C14—C15—C16—C11	0.9 (2)
F1—C5—C6—C7	−179.92 (14)	C12—C11—C16—F4	177.85 (13)
C4—C5—C6—C7	−0.1 (2)	C10—C11—C16—F4	−0.3 (2)
C5—C6—C7—C8	0.6 (2)	C12—C11—C16—C15	−0.9 (2)
C6—C7—C8—C9	−0.3 (2)	C10—C11—C16—C15	−178.99 (15)
C7—C8—C9—F2	179.95 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···N1ⁱ	0.93	2.58	3.392 (2)	146
C3—H3A···N2	0.97	2.36	2.8155 (18)	108
C3—H3B···F2	0.97	2.41	2.8508 (15)	107
C3—H3B···F3ⁱⁱ	0.97	2.47	3.0226 (16)	116
C8—H8A···F4ⁱⁱⁱ	0.93	2.54	3.144 (2)	123
C10—H10A···S1	0.97	2.53	3.0738 (14)	115
C10—H10B···F3	0.97	2.40	2.8453 (16)	107
C10—H10B···N2^iv	0.97	2.56	3.4191 (17)	148

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₁F₄N₃S
M_r	353.34
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	100
a, b, c (Å)	32.6678 (6), 5.8515 (1), 7.8140 (2)
V (Å³)	1493.69 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.46 × 0.33 × 0.14

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.887, 0.965
No. of measured, independent and observed [I > 2σ(I)] reflections	17980, 4796, 4299
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.756

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.076, 1.02
No. of reflections	4796
No. of parameters	218
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.26
Absolute structure	Flack (1983), 1935 Friedel pairs
Absolute structure parameter	0.20 (5)

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), 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
C1—H1A···N1ⁱ	0.93	2.58	3.392 (2)	146
C3—H3B···F3ⁱⁱ	0.97	2.47	3.0226 (16)	116
C8—H8A···F4ⁱⁱⁱ	0.93	2.54	3.144 (2)	123
C10—H10B···N2^iv	0.97	2.56	3.4191 (17)	148

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and WCL thank Universiti Sains Malaysia (USM) for a Research University Golden Goose Grant (No. 1001/PFIZIK/811012). WCL thanks USM for a USM Fellowship. AMI is grateful to the Director, NITK Surathkal, India, for providing research facilities.

References

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