3-Amino-N-benzyl-6-(4-fluoro­phen­yl)thieno[2,3-b]pyridine-2-carboxamide

Zhao, J.-N.; Yang, S.-Y.; Yang, L.

doi:10.1107/S160053681202212X

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1823

doi:10.1107/S160053681202212X

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3-Amino-N-benzyl-6-(4-fluorophenyl)thieno[2,3-b]pyridine-2-carboxamide

Jin-Ni Zhao,^a Sheng-Yong Yang ^a and Li Yang ^a ^*

^aState Key Laboratory of Biotherapy and Cancer Center, West China Hospital, West China Medical School, Sichuan University, Chengdu 610041, People's Republic of China
^*Correspondence e-mail: yangli@scu.edu.cn

(Received 12 April 2012; accepted 16 May 2012; online 19 May 2012)

In the title compound, C₂₁H₁₆FN₃OS, the thieno[2,3-b]pyridine system forms dihedral angles of 10.57 (12) and 83.87 (5)° with the fluorophenyl ring at the 6-position and the phenyl ring of the benzyl group, respectively. In the crystal, molecules are linked by weak N—H⋯N anf N—H⋯O hydrogen bonds and π–π stacking interactions involving fluorophenyl rings of adjacent molecules, with a centroid–centroid distance of 3.648 (10) Å. In addition, intramolecular N—H⋯S and N—H⋯O hydrogen bonds contribute to the stability of the molecular conformation.

Related literature

For the biological activity of thieno[2,3-b]pyridine derivatives, see: Litvinov et al. (2005 ).

Experimental

Crystal data

C₂₁H₁₆FN₃OS
M_r = 377.43
Monoclinic, P 2₁ /c
a = 18.9008 (7) Å
b = 9.9828 (4) Å
c = 9.5924 (4) Å
β = 102.224 (4)°
V = 1768.89 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 293 K
0.40 × 0.30 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.991, T_max = 1.000
7919 measured reflections
3609 independent reflections
2665 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.104
S = 1.03
3609 reflections
252 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯S1	0.86	2.68	3.0897 (16)	111
N3—H3⋯N2ⁱ	0.86	2.51	3.253 (2)	146
N2—H2B⋯O1	0.90 (2)	2.15 (2)	2.741 (2)	122.7 (17)
N2—H2B⋯O1ⁱⁱ	0.90 (2)	2.20 (2)	3.015 (2)	150.0 (17)
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x, -y, -z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: OLEX2.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681202212X/ds2191sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681202212X/ds2191Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681202212X/ds2191Isup3.cml

checkCIF report

Comment top

Thieno[2,3-b]pyridine derivatives are of great importance owing to their wide biological properties (Litvinov et al., 2005). The title compound is one of the key intermediates in our synthetic investigations of anticancer drugs. Herein we report its crystal structure.

As shown in Fig. 1, the thieno[2,3-b]pyridine ring forms dihedral angles of 10.57(0.12)° and 83.87(0.05)° with the monofluoro-benzene at 6-position and the phenyl rings at 2-position, respectively.In the crystal packing, stacking interactions involving phenyl rings containing fluorine atom of adjacent molecules are helpful for the stabilization of the crystal as well as intermolecular N—H···N hydrogen bonds.In addition,intramolecular N—H···O and N—H···S hydrogen bonds help to stabilize the molecular conformation (Table 1 and Fig.2).

Related literature top

For the biological activity of thieno[2,3-b]pyridine derivatives, see: Litvinov et al. (2005).

Experimental top

To a solution of 6-(4-fluorophenyl)-2-thioxo-1,2-dihydropyridine-3-carbonitrile (2.30 g, 10 mmol) in DMF (15.00 ml) was added dropwise a solution of 10% sodium hydroxide (8.00 ml). After stirring at room temperature for 0.5 h and then the temperature was raised to 85 °C and then 10% sodium hydroxide (8.00 ml) and N-benzyl-2-chloroacetamide (2.20 g, 12.0 mmol) were added. The reaction mixture was stirred under reflux until complete conversion of the starting materials (6 h, monitored by TLC). The mixture was then cooled to room temperature and crystallized to give 3.17 g of an yellow solid (84% yield).The product was recrystallized from ethanol to afford the title compound as an off-yellow solid (yield: 60%). Crystals suitable for X-ray analysis were obtained by slow evaporation using dichloromethane methanol (2:1 v/v) as eluent.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2006); cell refinement: CrysAlis PRO (Oxford Diffraction, 2006); data reduction: CrysAlis PRO (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2006); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. A packing diagram of the title compound, showing intermolecular hydrogen bonds of N—H···N as blue dashed lines,and intramolecular hydrogen bonds of N—H···O and N—H···S as green dashed lines

3-Amino-N-benzyl-6-(4-fluorophenyl)thieno[2,3-b]pyridine-2- carboxamide top

Crystal data top

C₂₁H₁₆FN₃OS	F(000) = 784
M_r = 377.43	D_x = 1.417 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.7107 Å
a = 18.9008 (7) Å	Cell parameters from 2427 reflections
b = 9.9828 (4) Å	θ = 3.0–29.2°
c = 9.5924 (4) Å	µ = 0.21 mm⁻¹
β = 102.224 (4)°	T = 293 K
V = 1768.89 (11) Å³	Block, yellow
Z = 4	0.40 × 0.30 × 0.10 mm

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	3609 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2665 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
Detector resolution: 16.0874 pixels mm^-1	θ_max = 26.4°, θ_min = 3.0°
ω scans	h = −21→23
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006)	k = −12→11
T_min = 0.991, T_max = 1.000	l = −11→11
7919 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0422P)² + 0.2875P] where P = (F_o² + 2F_c²)/3
3609 reflections	(Δ/σ)_max < 0.001
252 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₁H₁₆FN₃OS	V = 1768.89 (11) Å³
M_r = 377.43	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 18.9008 (7) Å	µ = 0.21 mm⁻¹
b = 9.9828 (4) Å	T = 293 K
c = 9.5924 (4) Å	0.40 × 0.30 × 0.10 mm
β = 102.224 (4)°

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	3609 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006)	2665 reflections with I > 2σ(I)
T_min = 0.991, T_max = 1.000	R_int = 0.021
7919 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.23 e Å⁻³
3609 reflections	Δρ_min = −0.23 e Å⁻³
252 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

	x	y	z	U_iso*/U_eq
S1	0.20491 (3)	0.22083 (5)	0.33501 (5)	0.04353 (16)
F1	0.68007 (7)	0.14850 (17)	0.54263 (17)	0.0879 (5)
O1	0.01663 (7)	0.12650 (13)	0.08498 (13)	0.0415 (3)
N1	0.34252 (8)	0.16214 (16)	0.32473 (17)	0.0430 (4)
N2	0.12841 (11)	0.01149 (18)	−0.01334 (18)	0.0431 (4)
N3	0.03925 (8)	0.26248 (15)	0.27578 (16)	0.0371 (4)
H3	0.0698	0.2893	0.3502	0.044*
C1	0.61019 (12)	0.1375 (3)	0.4718 (3)	0.0612 (6)
C2	0.55976 (13)	0.2160 (3)	0.5132 (3)	0.0649 (7)
H2	0.5730	0.2768	0.5876	0.078*
C3	0.48814 (12)	0.2039 (2)	0.4427 (3)	0.0588 (6)
H3A	0.4532	0.2570	0.4706	0.071*
C4	0.46761 (11)	0.1141 (2)	0.3312 (2)	0.0467 (5)
C5	0.52116 (12)	0.0370 (3)	0.2941 (3)	0.0629 (7)
H5	0.5088	−0.0248	0.2204	0.075*
C6	0.59308 (12)	0.0489 (3)	0.3640 (3)	0.0682 (7)
H6	0.6287	−0.0031	0.3369	0.082*
C7	0.38985 (11)	0.0995 (2)	0.2613 (2)	0.0441 (5)
C8	0.36703 (11)	0.0228 (2)	0.1384 (2)	0.0560 (6)
H8	0.4013	−0.0189	0.0964	0.067*
C9	0.29486 (11)	0.0081 (2)	0.0786 (2)	0.0514 (6)
H9	0.2799	−0.0429	−0.0035	0.062*
C10	0.24457 (10)	0.07078 (18)	0.14290 (19)	0.0363 (4)
C11	0.27268 (10)	0.14647 (18)	0.26477 (19)	0.0370 (4)
C12	0.16689 (10)	0.07362 (17)	0.10565 (19)	0.0335 (4)
C13	0.13826 (10)	0.15083 (17)	0.19911 (18)	0.0334 (4)
C14	0.06103 (10)	0.17874 (17)	0.18296 (18)	0.0322 (4)
C15	−0.03518 (10)	0.30762 (18)	0.2511 (2)	0.0383 (5)
H15A	−0.0510	0.3280	0.1504	0.046*
H15B	−0.0365	0.3905	0.3032	0.046*
C16	−0.08885 (10)	0.21225 (17)	0.29233 (18)	0.0337 (4)
C17	−0.16173 (11)	0.2454 (2)	0.2581 (2)	0.0465 (5)
H17	−0.1762	0.3236	0.2073	0.056*
C18	−0.21297 (12)	0.1646 (2)	0.2981 (3)	0.0582 (6)
H18	−0.2615	0.1892	0.2755	0.070*
C19	−0.19253 (12)	0.0472 (2)	0.3715 (2)	0.0540 (6)
H19	−0.2270	−0.0075	0.3988	0.065*
C20	−0.12068 (11)	0.0121 (2)	0.4037 (2)	0.0451 (5)
H20	−0.1066	−0.0674	0.4521	0.054*
C21	−0.06921 (10)	0.09380 (18)	0.36486 (19)	0.0382 (4)
H21	−0.0207	0.0689	0.3877	0.046*
H2A	0.1510 (12)	−0.042 (2)	−0.052 (2)	0.056 (7)*
H2B	0.0817 (12)	−0.005 (2)	−0.013 (2)	0.050 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0332 (3)	0.0534 (3)	0.0409 (3)	−0.0001 (2)	0.0009 (2)	−0.0129 (2)
F1	0.0331 (7)	0.1281 (13)	0.0949 (12)	−0.0129 (8)	−0.0034 (7)	0.0030 (10)
O1	0.0347 (7)	0.0465 (8)	0.0401 (8)	−0.0024 (6)	0.0006 (6)	−0.0115 (6)
N1	0.0315 (9)	0.0477 (10)	0.0467 (10)	−0.0001 (8)	0.0010 (8)	−0.0024 (8)
N2	0.0341 (10)	0.0547 (11)	0.0402 (10)	−0.0041 (9)	0.0074 (8)	−0.0145 (8)
N3	0.0326 (9)	0.0431 (9)	0.0338 (8)	−0.0009 (7)	0.0032 (7)	−0.0076 (7)
C1	0.0297 (12)	0.0809 (17)	0.0694 (16)	−0.0101 (12)	0.0023 (11)	0.0138 (14)
C2	0.0439 (14)	0.0742 (16)	0.0707 (17)	−0.0118 (13)	−0.0009 (12)	−0.0073 (13)
C3	0.0385 (13)	0.0658 (15)	0.0693 (16)	−0.0040 (12)	0.0050 (11)	−0.0043 (12)
C4	0.0320 (11)	0.0515 (12)	0.0553 (13)	−0.0018 (10)	0.0060 (10)	0.0072 (10)
C5	0.0375 (13)	0.0783 (17)	0.0714 (17)	0.0007 (12)	0.0083 (12)	−0.0095 (13)
C6	0.0351 (13)	0.0916 (19)	0.0772 (18)	0.0046 (13)	0.0108 (12)	−0.0017 (15)
C7	0.0341 (11)	0.0488 (12)	0.0481 (12)	0.0001 (10)	0.0057 (9)	0.0025 (9)
C8	0.0366 (12)	0.0725 (15)	0.0592 (14)	0.0053 (11)	0.0109 (11)	−0.0146 (12)
C9	0.0399 (12)	0.0651 (14)	0.0478 (13)	0.0023 (11)	0.0057 (10)	−0.0162 (10)
C10	0.0332 (10)	0.0390 (10)	0.0357 (10)	0.0003 (9)	0.0049 (8)	0.0007 (8)
C11	0.0320 (10)	0.0388 (10)	0.0379 (10)	−0.0003 (9)	0.0024 (8)	0.0020 (8)
C12	0.0337 (10)	0.0339 (9)	0.0317 (10)	−0.0023 (8)	0.0040 (8)	0.0024 (8)
C13	0.0319 (10)	0.0345 (10)	0.0318 (9)	−0.0022 (8)	0.0022 (8)	−0.0003 (8)
C14	0.0336 (10)	0.0316 (9)	0.0301 (9)	−0.0017 (8)	0.0040 (8)	0.0028 (7)
C15	0.0375 (11)	0.0389 (10)	0.0375 (11)	0.0074 (9)	0.0058 (9)	−0.0005 (8)
C16	0.0346 (10)	0.0358 (10)	0.0298 (9)	0.0027 (9)	0.0046 (8)	−0.0074 (7)
C17	0.0375 (12)	0.0476 (12)	0.0527 (13)	0.0085 (10)	0.0060 (10)	0.0030 (9)
C18	0.0320 (12)	0.0698 (15)	0.0725 (16)	0.0062 (12)	0.0104 (11)	−0.0006 (13)
C19	0.0427 (13)	0.0606 (14)	0.0607 (14)	−0.0075 (11)	0.0157 (11)	−0.0009 (11)
C20	0.0473 (13)	0.0445 (11)	0.0435 (12)	−0.0018 (10)	0.0094 (10)	0.0000 (9)
C21	0.0339 (11)	0.0447 (11)	0.0349 (10)	0.0043 (9)	0.0045 (8)	−0.0008 (8)

Geometric parameters (Å, º) top

S1—C11	1.7353 (19)	C7—C8	1.394 (3)
S1—C13	1.7548 (18)	C8—H8	0.9300
F1—C1	1.356 (2)	C8—C9	1.371 (3)
O1—C14	1.235 (2)	C9—H9	0.9300
N1—C7	1.339 (2)	C9—C10	1.387 (3)
N1—C11	1.333 (2)	C10—C11	1.399 (2)
N2—C12	1.366 (2)	C10—C12	1.436 (3)
N2—H2A	0.82 (2)	C12—C13	1.377 (2)
N2—H2B	0.90 (2)	C13—C14	1.462 (2)
N3—H3	0.8600	C15—H15A	0.9700
N3—C14	1.348 (2)	C15—H15B	0.9700
N3—C15	1.448 (2)	C15—C16	1.504 (3)
C1—C2	1.357 (3)	C16—C17	1.387 (3)
C1—C6	1.347 (3)	C16—C21	1.382 (2)
C2—H2	0.9300	C17—H17	0.9300
C2—C3	1.384 (3)	C17—C18	1.376 (3)
C3—H3A	0.9300	C18—H18	0.9300
C3—C4	1.386 (3)	C18—C19	1.379 (3)
C4—C5	1.377 (3)	C19—H19	0.9300
C4—C7	1.488 (3)	C19—C20	1.373 (3)
C5—H5	0.9300	C20—H20	0.9300
C5—C6	1.388 (3)	C20—C21	1.380 (3)
C6—H6	0.9300	C21—H21	0.9300

C11—S1—C13	90.80 (9)	C11—C10—C12	112.62 (16)
C11—N1—C7	116.41 (17)	N1—C11—S1	121.82 (15)
C12—N2—H2A	116.1 (16)	N1—C11—C10	126.18 (18)
C12—N2—H2B	115.6 (13)	C10—C11—S1	112.00 (14)
H2A—N2—H2B	119 (2)	N2—C12—C10	122.31 (17)
C14—N3—H3	119.8	N2—C12—C13	125.82 (18)
C14—N3—C15	120.47 (15)	C13—C12—C10	111.78 (16)
C15—N3—H3	119.8	C12—C13—S1	112.79 (14)
F1—C1—C2	118.5 (2)	C12—C13—C14	123.99 (16)
C6—C1—F1	119.2 (2)	C14—C13—S1	123.12 (13)
C6—C1—C2	122.3 (2)	O1—C14—N3	120.75 (17)
C1—C2—H2	120.6	O1—C14—C13	120.16 (16)
C1—C2—C3	118.8 (2)	N3—C14—C13	119.09 (16)
C3—C2—H2	120.6	N3—C15—H15A	108.2
C2—C3—H3A	119.4	N3—C15—H15B	108.2
C2—C3—C4	121.2 (2)	N3—C15—C16	116.49 (15)
C4—C3—H3A	119.4	H15A—C15—H15B	107.3
C3—C4—C7	119.98 (19)	C16—C15—H15A	108.2
C5—C4—C3	117.4 (2)	C16—C15—H15B	108.2
C5—C4—C7	122.6 (2)	C17—C16—C15	118.56 (16)
C4—C5—H5	119.1	C21—C16—C15	123.34 (17)
C4—C5—C6	121.7 (2)	C21—C16—C17	118.10 (18)
C6—C5—H5	119.1	C16—C17—H17	119.5
C1—C6—C5	118.6 (2)	C18—C17—C16	121.10 (19)
C1—C6—H6	120.7	C18—C17—H17	119.5
C5—C6—H6	120.7	C17—C18—H18	119.9
N1—C7—C4	116.12 (18)	C17—C18—C19	120.2 (2)
N1—C7—C8	121.59 (18)	C19—C18—H18	119.9
C8—C7—C4	122.28 (19)	C18—C19—H19	120.4
C7—C8—H8	119.5	C20—C19—C18	119.2 (2)
C9—C8—C7	121.0 (2)	C20—C19—H19	120.4
C9—C8—H8	119.5	C19—C20—H20	119.7
C8—C9—H9	120.6	C19—C20—C21	120.6 (2)
C8—C9—C10	118.70 (19)	C21—C20—H20	119.7
C10—C9—H9	120.6	C16—C21—H21	119.6
C9—C10—C11	116.14 (18)	C20—C21—C16	120.79 (18)
C9—C10—C12	131.23 (18)	C20—C21—H21	119.6

S1—C13—C14—O1	179.94 (13)	C9—C10—C11—N1	−0.9 (3)
S1—C13—C14—N3	0.3 (2)	C9—C10—C12—N2	−2.3 (3)
F1—C1—C2—C3	−179.1 (2)	C9—C10—C12—C13	−179.1 (2)
F1—C1—C6—C5	178.8 (2)	C10—C12—C13—S1	−0.40 (19)
N1—C7—C8—C9	−0.5 (3)	C10—C12—C13—C14	176.11 (16)
N2—C12—C13—S1	−177.12 (15)	C11—S1—C13—C12	0.46 (14)
N2—C12—C13—C14	−0.6 (3)	C11—S1—C13—C14	−176.09 (15)
N3—C15—C16—C17	−173.84 (16)	C11—N1—C7—C4	−178.27 (17)
N3—C15—C16—C21	7.2 (2)	C11—N1—C7—C8	0.5 (3)
C1—C2—C3—C4	−0.3 (4)	C11—C10—C12—N2	176.96 (16)
C2—C1—C6—C5	−0.6 (4)	C11—C10—C12—C13	0.1 (2)
C2—C3—C4—C5	0.4 (3)	C12—C10—C11—S1	0.2 (2)
C2—C3—C4—C7	177.6 (2)	C12—C10—C11—N1	179.78 (17)
C3—C4—C5—C6	−0.7 (4)	C12—C13—C14—O1	3.8 (3)
C3—C4—C7—N1	−9.0 (3)	C12—C13—C14—N3	−175.88 (16)
C3—C4—C7—C8	172.3 (2)	C13—S1—C11—N1	−179.96 (16)
C4—C5—C6—C1	0.8 (4)	C13—S1—C11—C10	−0.39 (14)
C4—C7—C8—C9	178.2 (2)	C14—N3—C15—C16	80.5 (2)
C5—C4—C7—N1	167.95 (19)	C15—N3—C14—O1	−8.7 (3)
C5—C4—C7—C8	−10.8 (3)	C15—N3—C14—C13	170.97 (15)
C6—C1—C2—C3	0.4 (4)	C15—C16—C17—C18	−177.43 (18)
C7—N1—C11—S1	179.73 (14)	C15—C16—C21—C20	178.02 (17)
C7—N1—C11—C10	0.2 (3)	C16—C17—C18—C19	−1.0 (3)
C7—C4—C5—C6	−177.7 (2)	C17—C16—C21—C20	−0.9 (3)
C7—C8—C9—C10	−0.2 (3)	C17—C18—C19—C20	−0.2 (3)
C8—C9—C10—C11	0.8 (3)	C18—C19—C20—C21	0.8 (3)
C8—C9—C10—C12	180.0 (2)	C19—C20—C21—C16	−0.3 (3)
C9—C10—C11—S1	179.59 (15)	C21—C16—C17—C18	1.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···S1	0.86	2.68	3.0897 (16)	111
N3—H3···N2ⁱ	0.86	2.51	3.253 (2)	146
N2—H2B···O1	0.90 (2)	2.15 (2)	2.741 (2)	122.7 (17)
N2—H2B···O1ⁱⁱ	0.90 (2)	2.20 (2)	3.015 (2)	150.0 (17)

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

Experimental details

Crystal data
Chemical formula	C₂₁H₁₆FN₃OS
M_r	377.43
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	18.9008 (7), 9.9828 (4), 9.5924 (4)
β (°)	102.224 (4)
V (Å³)	1768.89 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.40 × 0.30 × 0.10

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2006)
T_min, T_max	0.991, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7919, 3609, 2665
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.104, 1.03
No. of reflections	3609
No. of parameters	252
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.23

Computer programs: CrysAlis PRO (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2006), OLEX2 (Dolomanov et al., 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···S1	0.86	2.68	3.0897 (16)	110.8
N3—H3···N2ⁱ	0.86	2.51	3.253 (2)	145.6
N2—H2B···O1	0.90 (2)	2.15 (2)	2.741 (2)	122.7 (17)
N2—H2B···O1ⁱⁱ	0.90 (2)	2.20 (2)	3.015 (2)	150.0 (17)

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

Acknowledgements

We thank the Analytical and Testing Center of Sichuan University for the X-ray measurements.

References

Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Oxford Diffraction (2006). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England. Google Scholar
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