6-(1-Adamant­yl)-3-(2-fluoro­phen­yl)-1,2,4-triazolo[3,4-b][1,3,4]thia­diazole

Khan, M.-H.; Hameed, S.; Tahir, M.N.; Bokhari, T.H.; Khan, I.U.

doi:10.1107/S1600536809019692

organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1437

doi:10.1107/S1600536809019692

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6-(1-Adamantyl)-3-(2-fluorophenyl)-1,2,4-triazolo[3,4-b][1,3,4]thiadiazole

Mahmood-ul-Hassan Khan,^a Shahid Hameed,^a ‡ M. Nawaz Tahir,^b ^* Tanveer Hussain Bokhari ^c and Islam Ullah Khan ^c

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, ^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan, and ^cDepartment of Chemistry, Government College University, Lahore, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 24 May 2009; accepted 24 May 2009; online 29 May 2009)

In the title compound, C₁₉H₁₉FN₄S, the planes of the 2-fluorophenyl and 1,2,4-triazolo[3,4-b][1,3,4]thiadiazole ring systems are oriented at a dihedral angle of 48.98 (6)°. In the crystal, weak C—H⋯S and C—H⋯π interactions may help to establish the packing and π–π interactions between the centroids of the benzene rings at a distance of 3.8792 (13) Å occur.

Related literature

For a related structure, see: Holm et al. (2008 ). For our previous studies on related compounds, see: Akhtar et al. (2007 , 2008a ,b ). For background to the biological activity of related compounds, see: El-Emam et al. (2004 ); Kadi et al. (2007 ); Zhang et al. (2002 ).

Experimental

Crystal data

C₁₉H₁₉FN₄S
M_r = 354.44
Orthorhombic, P b c a
a = 13.2684 (9) Å
b = 12.4293 (9) Å
c = 20.2231 (15) Å
V = 3335.1 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 296 K
0.25 × 0.22 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.945, T_max = 0.956
22695 measured reflections
4486 independent reflections
3116 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.136
S = 1.04
4486 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯S1ⁱ	0.97	2.84	3.640 (2)	140
C12—H12⋯Cg1ⁱⁱ	0.98	2.90	3.713 (2)	140
C18—H18B⋯Cg1ⁱⁱⁱ	0.97	2.83	3.787 (3)	170
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ . Cg1 is the centroid of the S1/C8/N3/N4/C9 ring.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809019692/hb2984sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809019692/hb2984Isup2.hkl

checkCIF report

Comment top

Five membered heterocycles bearing adamantyl moiety are gaining importance due to their promising biological activities (El-Emam et al., 2004; Kadi et al., 2007). On the other hand the condensed heterocyclic systems e.g., triazolothiadiazoles exhibit numerous biological activities (Zhang et al., 2002). In continuation of our previous studeis (Akhtar et al., 2007, 2008a, 2008b), the title compound, (I), (Fig. 1), has been synthesized with the hope that it will possess antiviral and anticancer activity. The crystal structure of (II) 3-(2-Fluorophenyl)-6-(phenoxymethyl)-1,2,4- triazolo(3,4 - b)(1,3,4)thiadiazole (Holm, et al., 2008) has been published which has a common moiety as in (I).

In (I), the ring A (C1—C6) along with F1-atom and two [(C7/N1/N2/C8/N3) & (C8/S1/C9/N4/N3)] fused heterocyclic rings B (C7/N1/N2/C8/S1/C9/N4/N3) are planar and oriented at a dihedral angle of 48.98 (6)°. There exist π—π interaction between the centroids, CgA—CgAⁱ [symmetry code: i = 1 - x, -y, 1 - z], of benzene rings at a distance of 3.8792 (13) Å. In the crystal, the packing is consolidated by H-bonding (Fig 2) and C—H···π interactions (Table 1).

Related literature top

For a related structure, see: Holm et al. (2008). For our previous studies on related compounds, see: Akhtar et al. (2007, 2008a,b). For background to the biological activity of related compounds, see: El-Emam et al. (2004); Kadi et al. (2007); Zhang et al. (2002). Cg1 is the centroid of the S1/C8/N3/N4/C9 ring.

Experimental top

A mixture of 4-amino-5-(2-fluorophenyl)-2H-1,2,4-triazole-3(4H)-thione (0.2 g, 0.56 mmol) and adamantane-1-carboxylic acid (0.10 g, 0.56 mmol) in the presence of POCl₃ (5 ml) was refluxed for four hours. The reaction mixture was cooled to room temperature, poured into crushed ice and neutralized using solid potassium carbonate until pH was 8. The precipitated solid was filtered, washed with excess water and recrystallized from chloroform to yield colourless prisms of (I).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of (I) with displacement ellipsoids drawn at the 30% probability level. H-atoms are shown by small spheres of arbitrary radius.
	Fig. 2. Partial packing diagram for (I) showing the C—H···S interaction as a dashed line.

6-(1-Adamantyl)-3-(2-fluorophenyl)-1,2,4- triazolo[3,4-b][1,3,4]thiadiazole top

Crystal data top

C₁₉H₁₉FN₄S	F(000) = 1488
M_r = 354.44	D_x = 1.412 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3116 reflections
a = 13.2684 (9) Å	θ = 2.5–29.1°
b = 12.4293 (9) Å	µ = 0.21 mm⁻¹
c = 20.2231 (15) Å	T = 296 K
V = 3335.1 (4) Å³	Prism, colourless
Z = 8	0.25 × 0.22 × 0.20 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	4486 independent reflections
Radiation source: fine-focus sealed tube	3116 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
Detector resolution: 7.40 pixels mm^-1	θ_max = 29.1°, θ_min = 2.5°
ω scans	h = −12→18
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −17→14
T_min = 0.945, T_max = 0.956	l = −26→27
22695 measured reflections

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.136	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0579P)² + 1.3259P] where P = (F_o² + 2F_c²)/3
4486 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₉H₁₉FN₄S	V = 3335.1 (4) Å³
M_r = 354.44	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 13.2684 (9) Å	µ = 0.21 mm⁻¹
b = 12.4293 (9) Å	T = 296 K
c = 20.2231 (15) Å	0.25 × 0.22 × 0.20 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	4486 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3116 reflections with I > 2σ(I)
T_min = 0.945, T_max = 0.956	R_int = 0.031
22695 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.136	H-atom parameters constrained
S = 1.04	Δρ_max = 0.35 e Å⁻³
4486 reflections	Δρ_min = −0.28 e Å⁻³
235 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.25232 (4)	−0.15058 (4)	0.23126 (2)	0.0517 (2)
F1	0.35571 (14)	−0.27396 (11)	0.52074 (7)	0.0839 (6)
N1	0.20243 (13)	−0.22822 (13)	0.41446 (9)	0.0543 (6)
N2	0.17459 (14)	−0.24778 (14)	0.34844 (9)	0.0591 (6)
N3	0.29443 (10)	−0.12526 (11)	0.35182 (7)	0.0360 (4)
N4	0.36117 (10)	−0.05549 (11)	0.32199 (7)	0.0343 (4)
C1	0.32252 (13)	−0.10525 (14)	0.47314 (9)	0.0392 (5)
C2	0.36251 (16)	−0.16551 (17)	0.52410 (10)	0.0517 (6)
C3	0.41073 (19)	−0.1200 (2)	0.57717 (10)	0.0639 (8)
C4	0.41784 (17)	−0.0094 (2)	0.58048 (10)	0.0611 (8)
C5	0.37749 (16)	0.05301 (18)	0.53119 (10)	0.0549 (7)
C6	0.33120 (14)	0.00584 (15)	0.47758 (9)	0.0463 (6)
C7	0.27374 (13)	−0.15494 (14)	0.41576 (9)	0.0403 (5)
C8	0.23167 (13)	−0.18403 (14)	0.31343 (10)	0.0437 (5)
C9	0.34740 (12)	−0.06062 (13)	0.25887 (8)	0.0348 (5)
C10	0.40431 (12)	0.00535 (13)	0.20943 (8)	0.0337 (4)
C11	0.48759 (15)	0.07039 (18)	0.24376 (9)	0.0504 (6)
C12	0.54359 (15)	0.13979 (18)	0.19241 (10)	0.0543 (7)
C13	0.47109 (16)	0.21626 (17)	0.15982 (11)	0.0581 (7)
C14	0.38813 (17)	0.15387 (18)	0.12638 (12)	0.0626 (8)
C15	0.33138 (15)	0.08502 (16)	0.17677 (11)	0.0527 (6)
C16	0.4512 (2)	−0.06639 (17)	0.15637 (11)	0.0657 (8)
C17	0.5082 (3)	0.0039 (2)	0.10590 (12)	0.0802 (9)
C18	0.59042 (18)	0.0674 (2)	0.14102 (13)	0.0730 (9)
C19	0.4329 (3)	0.0822 (2)	0.07399 (11)	0.0855 (10)
H3	0.43812	−0.16293	0.61028	0.0767*
H4	0.45004	0.02286	0.61619	0.0733*
H5	0.38143	0.12757	0.53400	0.0658*
H6	0.30545	0.04888	0.44397	0.0555*
H11A	0.45818	0.11629	0.27742	0.0604*
H11B	0.53468	0.02185	0.26512	0.0604*
H12	0.59673	0.18097	0.21460	0.0651*
H13A	0.44245	0.26409	0.19273	0.0697*
H13B	0.50652	0.25966	0.12744	0.0697*
H14	0.34099	0.20433	0.10564	0.0751*
H15A	0.30145	0.13091	0.21022	0.0633*
H15B	0.27764	0.04595	0.15483	0.0633*
H16A	0.49735	−0.11705	0.17670	0.0789*
H16B	0.39877	−0.10692	0.13405	0.0789*
H17	0.53836	−0.04191	0.07176	0.0963*
H18A	0.62742	0.11032	0.10915	0.0876*
H18B	0.63734	0.01826	0.16203	0.0876*
H19A	0.37972	0.04208	0.05216	0.1027*
H19B	0.46694	0.12570	0.04103	0.1027*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0578 (3)	0.0481 (3)	0.0492 (3)	−0.0163 (2)	−0.0141 (2)	−0.0060 (2)
F1	0.1293 (14)	0.0492 (8)	0.0733 (9)	0.0040 (8)	−0.0198 (9)	0.0189 (7)
N1	0.0552 (10)	0.0455 (9)	0.0623 (11)	−0.0141 (8)	−0.0018 (8)	0.0070 (8)
N2	0.0611 (10)	0.0483 (9)	0.0678 (12)	−0.0202 (8)	−0.0068 (9)	0.0020 (9)
N3	0.0342 (7)	0.0312 (7)	0.0427 (8)	−0.0025 (5)	−0.0031 (6)	−0.0002 (6)
N4	0.0330 (7)	0.0324 (7)	0.0375 (7)	−0.0016 (5)	−0.0019 (6)	−0.0014 (6)
C1	0.0351 (8)	0.0425 (9)	0.0401 (9)	−0.0011 (7)	0.0052 (7)	0.0042 (7)
C2	0.0615 (12)	0.0487 (11)	0.0450 (10)	0.0004 (9)	0.0043 (9)	0.0110 (9)
C3	0.0733 (15)	0.0777 (16)	0.0407 (10)	0.0016 (12)	−0.0069 (10)	0.0148 (10)
C4	0.0616 (13)	0.0810 (16)	0.0406 (10)	−0.0128 (12)	0.0007 (9)	−0.0047 (10)
C5	0.0585 (12)	0.0528 (12)	0.0533 (12)	−0.0067 (10)	0.0026 (10)	−0.0077 (9)
C6	0.0470 (10)	0.0432 (10)	0.0487 (10)	−0.0015 (8)	−0.0022 (8)	0.0024 (8)
C7	0.0390 (9)	0.0342 (8)	0.0478 (10)	−0.0005 (7)	0.0006 (7)	0.0048 (7)
C8	0.0425 (9)	0.0356 (9)	0.0530 (10)	−0.0064 (7)	−0.0083 (8)	−0.0036 (8)
C9	0.0338 (8)	0.0313 (7)	0.0394 (9)	0.0013 (6)	−0.0055 (7)	−0.0054 (7)
C10	0.0355 (8)	0.0340 (8)	0.0315 (7)	0.0043 (6)	−0.0038 (6)	−0.0048 (6)
C11	0.0423 (10)	0.0682 (13)	0.0406 (9)	−0.0147 (9)	−0.0045 (8)	0.0014 (9)
C12	0.0401 (10)	0.0728 (14)	0.0499 (11)	−0.0137 (9)	−0.0001 (8)	0.0052 (10)
C13	0.0550 (12)	0.0478 (11)	0.0716 (14)	−0.0041 (9)	0.0134 (11)	0.0044 (10)
C14	0.0527 (12)	0.0602 (13)	0.0748 (15)	0.0024 (10)	−0.0127 (11)	0.0291 (12)
C15	0.0402 (10)	0.0453 (10)	0.0727 (13)	0.0009 (8)	−0.0095 (9)	0.0140 (10)
C16	0.0922 (18)	0.0451 (11)	0.0599 (13)	0.0105 (11)	0.0243 (12)	−0.0122 (10)
C17	0.123 (2)	0.0619 (15)	0.0558 (13)	0.0071 (15)	0.0433 (15)	−0.0135 (12)
C18	0.0537 (13)	0.0819 (17)	0.0834 (17)	0.0217 (12)	0.0285 (12)	0.0241 (14)
C19	0.114 (2)	0.105 (2)	0.0374 (11)	−0.0375 (19)	−0.0114 (13)	0.0115 (13)

Geometric parameters (Å, º) top

S1—C8	1.735 (2)	C14—C15	1.529 (3)
S1—C9	1.7758 (17)	C14—C19	1.506 (4)
F1—C2	1.353 (3)	C16—C17	1.542 (4)
N1—N2	1.407 (3)	C17—C18	1.522 (4)
N1—C7	1.314 (2)	C17—C19	1.537 (5)
N2—C8	1.305 (3)	C3—H3	0.9300
N3—N4	1.3784 (19)	C4—H4	0.9300
N3—C7	1.372 (2)	C5—H5	0.9300
N3—C8	1.353 (2)	C6—H6	0.9300
N4—C9	1.291 (2)	C11—H11A	0.9700
C1—C2	1.380 (3)	C11—H11B	0.9700
C1—C6	1.389 (3)	C12—H12	0.9800
C1—C7	1.465 (3)	C13—H13A	0.9700
C2—C3	1.372 (3)	C13—H13B	0.9700
C3—C4	1.380 (4)	C14—H14	0.9800
C4—C5	1.372 (3)	C15—H15A	0.9700
C5—C6	1.377 (3)	C15—H15B	0.9700
C9—C10	1.497 (2)	C16—H16A	0.9700
C10—C11	1.535 (3)	C16—H16B	0.9700
C10—C15	1.534 (3)	C17—H17	0.9800
C10—C16	1.528 (3)	C18—H18A	0.9700
C11—C12	1.541 (3)	C18—H18B	0.9700
C12—C13	1.504 (3)	C19—H19A	0.9700
C12—C18	1.509 (3)	C19—H19B	0.9700
C13—C14	1.507 (3)

C8—S1—C9	87.82 (8)	C2—C3—H3	121.00
N2—N1—C7	109.15 (16)	C4—C3—H3	121.00
N1—N2—C8	104.93 (16)	C3—C4—H4	120.00
N4—N3—C7	135.23 (14)	C5—C4—H4	120.00
N4—N3—C8	118.95 (14)	C4—C5—H5	120.00
C7—N3—C8	105.81 (14)	C6—C5—H5	120.00
N3—N4—C9	108.10 (13)	C1—C6—H6	120.00
C2—C1—C6	117.36 (17)	C5—C6—H6	120.00
C2—C1—C7	122.17 (17)	C10—C11—H11A	110.00
C6—C1—C7	120.47 (16)	C10—C11—H11B	110.00
F1—C2—C1	118.53 (18)	C12—C11—H11A	110.00
F1—C2—C3	118.78 (19)	C12—C11—H11B	110.00
C1—C2—C3	122.7 (2)	H11A—C11—H11B	108.00
C2—C3—C4	118.7 (2)	C11—C12—H12	109.00
C3—C4—C5	120.1 (2)	C13—C12—H12	109.00
C4—C5—C6	120.4 (2)	C18—C12—H12	109.00
C1—C6—C5	120.75 (18)	C12—C13—H13A	110.00
N1—C7—N3	108.16 (16)	C12—C13—H13B	110.00
N1—C7—C1	128.78 (17)	C14—C13—H13A	110.00
N3—C7—C1	122.99 (15)	C14—C13—H13B	110.00
S1—C8—N2	139.20 (16)	H13A—C13—H13B	108.00
S1—C8—N3	108.85 (13)	C13—C14—H14	109.00
N2—C8—N3	111.95 (18)	C15—C14—H14	109.00
S1—C9—N4	116.26 (12)	C19—C14—H14	109.00
S1—C9—C10	119.54 (12)	C10—C15—H15A	110.00
N4—C9—C10	124.18 (15)	C10—C15—H15B	110.00
C9—C10—C11	110.45 (14)	C14—C15—H15A	110.00
C9—C10—C15	108.84 (14)	C14—C15—H15B	110.00
C9—C10—C16	110.78 (14)	H15A—C15—H15B	108.00
C11—C10—C15	107.99 (15)	C10—C16—H16A	110.00
C11—C10—C16	109.38 (16)	C10—C16—H16B	110.00
C15—C10—C16	109.35 (15)	C17—C16—H16A	110.00
C10—C11—C12	109.70 (15)	C17—C16—H16B	110.00
C11—C12—C13	109.91 (17)	H16A—C16—H16B	108.00
C11—C12—C18	109.21 (18)	C16—C17—H17	110.00
C13—C12—C18	109.78 (18)	C18—C17—H17	110.00
C12—C13—C14	109.79 (18)	C19—C17—H17	110.00
C13—C14—C15	110.41 (19)	C12—C18—H18A	110.00
C13—C14—C19	109.4 (2)	C12—C18—H18B	110.00
C15—C14—C19	109.39 (19)	C17—C18—H18A	110.00
C10—C15—C14	109.73 (16)	C17—C18—H18B	110.00
C10—C16—C17	109.51 (17)	H18A—C18—H18B	108.00
C16—C17—C18	109.7 (2)	C14—C19—H19A	110.00
C16—C17—C19	108.5 (3)	C14—C19—H19B	110.00
C18—C17—C19	109.5 (2)	C17—C19—H19A	110.00
C12—C18—C17	109.6 (2)	C17—C19—H19B	110.00
C14—C19—C17	109.61 (19)	H19A—C19—H19B	108.00

C9—S1—C8—N2	−179.0 (2)	C4—C5—C6—C1	1.5 (3)
C9—S1—C8—N3	1.05 (13)	S1—C9—C10—C11	−175.71 (12)
C8—S1—C9—N4	−0.64 (14)	S1—C9—C10—C15	65.90 (17)
C8—S1—C9—C10	−179.31 (14)	S1—C9—C10—C16	−54.36 (19)
C7—N1—N2—C8	−0.1 (2)	N4—C9—C10—C11	5.7 (2)
N2—N1—C7—N3	−0.2 (2)	N4—C9—C10—C15	−112.66 (18)
N2—N1—C7—C1	176.70 (17)	N4—C9—C10—C16	127.08 (18)
N1—N2—C8—S1	−179.67 (17)	C9—C10—C11—C12	−178.63 (15)
N1—N2—C8—N3	0.3 (2)	C15—C10—C11—C12	−59.7 (2)
C7—N3—N4—C9	179.60 (18)	C16—C10—C11—C12	59.2 (2)
C8—N3—N4—C9	0.9 (2)	C9—C10—C15—C14	179.60 (16)
N4—N3—C7—N1	−178.48 (16)	C11—C10—C15—C14	59.7 (2)
N4—N3—C7—C1	4.4 (3)	C16—C10—C15—C14	−59.3 (2)
C8—N3—C7—N1	0.33 (19)	C9—C10—C16—C17	179.4 (2)
C8—N3—C7—C1	−176.77 (16)	C11—C10—C16—C17	−58.6 (2)
N4—N3—C8—S1	−1.38 (18)	C15—C10—C16—C17	59.5 (2)
N4—N3—C8—N2	178.67 (15)	C10—C11—C12—C13	60.2 (2)
C7—N3—C8—S1	179.58 (12)	C10—C11—C12—C18	−60.3 (2)
C7—N3—C8—N2	−0.4 (2)	C11—C12—C13—C14	−59.2 (2)
N3—N4—C9—S1	0.02 (17)	C18—C12—C13—C14	61.0 (2)
N3—N4—C9—C10	178.62 (14)	C11—C12—C18—C17	61.0 (2)
C6—C1—C2—F1	−179.52 (18)	C13—C12—C18—C17	−59.6 (2)
C6—C1—C2—C3	−1.0 (3)	C12—C13—C14—C15	59.4 (2)
C7—C1—C2—F1	−0.3 (3)	C12—C13—C14—C19	−61.0 (2)
C7—C1—C2—C3	178.2 (2)	C13—C14—C15—C10	−60.1 (2)
C2—C1—C6—C5	−0.4 (3)	C19—C14—C15—C10	60.3 (2)
C7—C1—C6—C5	−179.61 (18)	C13—C14—C19—C17	59.7 (3)
C2—C1—C7—N1	50.7 (3)	C15—C14—C19—C17	−61.4 (3)
C2—C1—C7—N3	−132.83 (19)	C10—C16—C17—C18	59.5 (3)
C6—C1—C7—N1	−130.1 (2)	C10—C16—C17—C19	−60.1 (2)
C6—C1—C7—N3	46.3 (3)	C16—C17—C18—C12	−60.8 (3)
F1—C2—C3—C4	179.9 (2)	C19—C17—C18—C12	58.2 (3)
C1—C2—C3—C4	1.3 (3)	C16—C17—C19—C14	61.2 (3)
C2—C3—C4—C5	−0.3 (3)	C18—C17—C19—C14	−58.5 (3)
C3—C4—C5—C6	−1.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···S1ⁱ	0.97	2.84	3.640 (2)	140
C12—H12···Cg1ⁱⁱ	0.98	2.90	3.713 (2)	140
C18—H18B···Cg1ⁱⁱⁱ	0.97	2.83	3.787 (3)	170

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₉FN₄S
M_r	354.44
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	13.2684 (9), 12.4293 (9), 20.2231 (15)
V (Å³)	3335.1 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.25 × 0.22 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.945, 0.956
No. of measured, independent and observed [I > 2σ(I)] reflections	22695, 4486, 3116
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.685

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.136, 1.04
No. of reflections	4486
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.28

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···S1ⁱ	0.97	2.84	3.640 (2)	140
C12—H12···Cg1ⁱⁱ	0.98	2.90	3.713 (2)	140
C18—H18B···Cg1ⁱⁱⁱ	0.97	2.83	3.787 (3)	170

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

Footnotes

‡Additional correspondence author for matters regarding the chemistry, e-mail: shameed@qau.edu.pk.

Acknowledgements

The authors acknowledge the Higher Education Commission, Islamabad, Pakistan, and Bana International, Karachi, Pakistan, for funding the purchase of the diffractometer and for technical support, respectively.

References

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