(E)-N-[Cyclo­pent­yl(morpholin-4-yl)­methylid­ene]-4-fluoro­benzene­sulfonamide

Efimov, I.; Slepukhin, P.; Beliaev, N.; Bakulev, V.

doi:10.1107/S2414314616000134

organic compounds

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ISSN: 2414-3146

Volume 1| Part 1| January 2016| x160013

doi:10.1107/S2414314616000134

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(E)-N-[Cyclopentyl(morpholin-4-yl)methylidene]-4-fluorobenzenesulfonamide

Ilya Efimov,^a ^* Pavel Slepukhin,^b Nikolai Beliaev ^a and Vasiliy Bakulev ^a

^aUral Federal University, Mira 19 Ekaterinburg 620002, Russian Federation, and ^bI. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of Russian Academy, of Sciences, 20 S. Kovalevskaya str., 620990 Ekaterinburg, Russia
^*Correspondence e-mail: aspirant_efimov@mail.ru

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 17 December 2015; accepted 4 January 2016; online 23 January 2016)

The title compound, C₁₆H₂₁FN₂O₃S, was obtained from the reaction between sulfonyl azide, cyclohexanone and morpholine. The bond lengths at the amidine N—C—N grouping are similar [1.326 (3) and 1.338 (3) Å], indicating significant conjugation. The cyclopentyl moiety displays disorder of one of the methylene groups into two orientations with occupancy coefficients 0.75/0.25. No shortened intermolecular contacts in the crystal are observed.

Keywords: crystal structure; amidines; transformation.

CCDC reference: 1445312

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Chemical scheme

Structure description

The title compound is illustrated in Fig. 1. For background to sulfonamides, see: Xu et al. (2008 ); Xie et al. (2015 ).

Figure 1
The title compound.

Synthesis and crystallization

In a 10-ml tube with a stirring bar, 4-fluorobenzene-1-sulfonyl azide (1 mmol, 201 mg), cyclohexanone (2 mmol, 206 ml), morpholine (2 mmol, 173 ml) and 2 ml methanol were added successively; the mixture was then stirred at room temperature. After cooling down, the volatiles were removed under reduced pressure (Fig. 2). To the residue was added 5% water solution of CH₃COOH and mixture was stirred over 2 h. The resulting precipitate was filtered off, washed with water, dried and recrystallized from water.

Figure 2
Reaction scheme.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1.

Table 1
Experimental details

Crystal data
Chemical formula	C₁₆H₂₁FN₂O₃S
M_r	340.41
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	11.5613 (7), 16.4245 (13), 8.8730 (6)
β (°)	107.768 (6)
V (Å³)	1604.5 (2)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.23
Crystal size (mm)	0.25 × 0.17 × 0.03

Data collection
Diffractometer	Agilent Xcalibur, Eos diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2013 )
T_min, T_max	0.939, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	6974, 3391, 2323
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.641

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.137, 1.01
No. of reflections	3391
No. of parameters	221
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.38
Computer programs: CrysAlis PRO (Agilent, 2013), SHELXS (Sheldrick, 2008 ), SHELXL (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009 ).

Structural data

CCDC reference: 1445312

Crystal structure: contains datablock I. DOI: 10.1107/S2414314616000134/hb4006sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616000134/hb4006Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616000134/hb4006Isup3.cml

checkCIF report

Experimental top

In a 10-ml tube with a stirring bar, 4-fluorobenzene-1-sulfonyl azide (1 mmol, 201 mg), cyclohexanone (2 mmol, 206 ml), morpholine (2 mmol, 173 ml) and 2 ml me thanol were added successively; the mixture was then stirred at room temperature. After cooling down, the volatiles were removed under reduced pressure (Fig. 2)).. To the residue was added 5% water solution of CH₃COOH and mixture was stirred over 2 h. The resulting precipitate was filtered off, washed with water, dried and recrystallized from water.

Structure description top

The title compound is illustrated in Fig. 1. For background to sulfonamides, see: Xu et al. (2008); Xie et al. (2015).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

	Fig. 1. Please provide caption, including probability level.
	Fig. 2. Reaction scheme.

(E)-N-[Cyclopentyl(morpholin-4-yl)methylidene]-4-fluorobenzenesulfonamide top

Crystal data top

C₁₆H₂₁FN₂O₃S	F(000) = 720
M_r = 340.41	D_x = 1.409 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.7107 Å
a = 11.5613 (7) Å	Cell parameters from 1405 reflections
b = 16.4245 (13) Å	θ = 2.8–27.0°
c = 8.8730 (6) Å	µ = 0.23 mm⁻¹
β = 107.768 (6)°	T = 295 K
V = 1604.5 (2) Å³	Plank, colourless
Z = 4	0.25 × 0.17 × 0.03 mm

Data collection top

Agilent Xcalibur, Eos diffractometer	3391 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2323 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 15.9555 pixels mm^-1	θ_max = 27.1°, θ_min = 2.2°
ω scans	h = −9→14
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −21→18
T_min = 0.939, T_max = 1.000	l = −10→11
6974 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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.075P)² + 0.010P] where P = (F_o² + 2F_c²)/3
3391 reflections	(Δ/σ)_max < 0.001
221 parameters	Δρ_max = 0.29 e Å⁻³
6 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₁₆H₂₁FN₂O₃S	V = 1604.5 (2) Å³
M_r = 340.41	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.5613 (7) Å	µ = 0.23 mm⁻¹
b = 16.4245 (13) Å	T = 295 K
c = 8.8730 (6) Å	0.25 × 0.17 × 0.03 mm
β = 107.768 (6)°

Data collection top

Agilent Xcalibur, Eos diffractometer	3391 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	2323 reflections with I > 2σ(I)
T_min = 0.939, T_max = 1.000	R_int = 0.029
6974 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	6 restraints
wR(F²) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.29 e Å⁻³
3391 reflections	Δρ_min = −0.38 e Å⁻³
221 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	Occ. (<1)
S1	0.26452 (5)	0.09127 (4)	0.07277 (6)	0.04217 (19)
N2	0.45896 (15)	0.09749 (12)	−0.20031 (19)	0.0369 (4)
N1	0.37106 (15)	0.10138 (13)	−0.0054 (2)	0.0413 (5)
C1	0.14033 (18)	0.14851 (14)	−0.0468 (2)	0.0347 (5)
C7	0.36523 (18)	0.07661 (14)	−0.1498 (2)	0.0352 (5)
O1	0.22350 (16)	0.00860 (11)	0.07573 (19)	0.0568 (5)
C8	0.26032 (19)	0.02854 (15)	−0.2575 (2)	0.0381 (5)
O3	0.60684 (14)	0.19090 (11)	−0.33829 (19)	0.0528 (5)
F8	−0.14638 (14)	0.28150 (12)	−0.3150 (2)	0.0788 (5)
C2	0.1600 (2)	0.22178 (15)	−0.1115 (3)	0.0444 (6)
H2	0.2388	0.2406	−0.0946	0.053*
O2	0.30637 (15)	0.13122 (13)	0.22357 (18)	0.0605 (5)
C13	0.4793 (2)	0.07269 (15)	−0.3481 (2)	0.0419 (6)
H13A	0.4078	0.0450	−0.4148	0.050*
H13B	0.5472	0.0351	−0.3259	0.050*
C3	0.0632 (2)	0.26682 (16)	−0.2006 (3)	0.0523 (6)
H3	0.0754	0.3165	−0.2437	0.063*
C4	−0.0514 (2)	0.23724 (17)	−0.2248 (3)	0.0498 (6)
C16	0.56120 (19)	0.14650 (16)	−0.1027 (3)	0.0437 (6)
H16A	0.6336	0.1130	−0.0675	0.052*
H16B	0.5425	0.1665	−0.0099	0.052*
C14	0.5058 (2)	0.14643 (17)	−0.4328 (3)	0.0489 (6)
H14A	0.5216	0.1293	−0.5292	0.059*
H14B	0.4350	0.1815	−0.4621	0.059*
C5	−0.0748 (2)	0.16534 (17)	−0.1626 (3)	0.0503 (6)
H5	−0.1541	0.1472	−0.1801	0.060*
C9	0.1918 (2)	0.06850 (17)	−0.4184 (3)	0.0490 (6)
H9A	0.1177	0.0946	−0.4135	0.059*
H9B	0.2424	0.1088	−0.4477	0.059*
C6	0.0229 (2)	0.12052 (15)	−0.0730 (3)	0.0446 (6)
H6	0.0097	0.0711	−0.0298	0.053*
C12	0.2895 (2)	−0.05923 (15)	−0.2949 (3)	0.0490 (6)
H12A	0.3680	−0.0622	−0.3131	0.059*	0.75
H12B	0.2890	−0.0960	−0.2096	0.059*	0.75
H12C	0.2512	−0.0983	−0.2434	0.059*	0.25
H12D	0.3765	−0.0687	−0.2607	0.059*	0.25
C15	0.5838 (2)	0.21732 (16)	−0.1983 (3)	0.0509 (6)
H15A	0.5135	0.2529	−0.2260	0.061*
H15B	0.6528	0.2484	−0.1346	0.061*
C11	0.1861 (5)	−0.0793 (3)	−0.4464 (5)	0.0564 (12)	0.75
H11A	0.2104	−0.1217	−0.5066	0.068*	0.75
H11B	0.1141	−0.0970	−0.4213	0.068*	0.75
C10	0.1633 (3)	−0.0017 (2)	−0.5361 (3)	0.0769 (10)
H10A	0.0791	0.0011	−0.6013	0.092*	0.75
H10B	0.2143	0.0016	−0.6047	0.092*	0.75
H10C	0.0791	−0.0179	−0.5574	0.092*	0.25
H10D	0.1749	0.0157	−0.6350	0.092*	0.25
H8	0.2026 (19)	0.0260 (13)	−0.203 (2)	0.032 (5)*
C11A	0.2368 (14)	−0.0656 (11)	−0.477 (2)	0.067 (4)	0.25
H11C	0.3027	−0.0669	−0.5232	0.081*	0.25
H11D	0.1912	−0.1159	−0.5047	0.081*	0.25

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0421 (3)	0.0542 (4)	0.0311 (3)	0.0068 (3)	0.0124 (2)	0.0008 (2)
N2	0.0384 (9)	0.0416 (12)	0.0318 (10)	−0.0014 (8)	0.0121 (7)	−0.0063 (8)
N1	0.0360 (9)	0.0565 (14)	0.0311 (10)	0.0024 (9)	0.0099 (7)	−0.0061 (8)
C1	0.0356 (11)	0.0384 (13)	0.0321 (11)	−0.0013 (9)	0.0135 (8)	−0.0051 (9)
C7	0.0350 (11)	0.0366 (13)	0.0336 (12)	0.0057 (9)	0.0099 (8)	−0.0001 (8)
O1	0.0676 (11)	0.0494 (12)	0.0606 (11)	0.0099 (9)	0.0305 (9)	0.0175 (8)
C8	0.0383 (12)	0.0427 (14)	0.0342 (12)	−0.0046 (10)	0.0124 (9)	−0.0024 (9)
O3	0.0478 (9)	0.0614 (12)	0.0509 (10)	−0.0124 (8)	0.0176 (7)	−0.0003 (8)
F8	0.0623 (10)	0.0796 (14)	0.0833 (11)	0.0288 (9)	0.0054 (8)	0.0109 (9)
C2	0.0377 (12)	0.0426 (15)	0.0527 (14)	−0.0070 (11)	0.0135 (10)	−0.0003 (11)
O2	0.0537 (10)	0.0952 (16)	0.0311 (9)	0.0093 (10)	0.0106 (7)	−0.0109 (9)
C13	0.0428 (12)	0.0485 (15)	0.0371 (13)	−0.0021 (10)	0.0162 (9)	−0.0069 (10)
C3	0.0590 (15)	0.0397 (15)	0.0577 (15)	0.0003 (12)	0.0170 (11)	0.0082 (11)
C4	0.0426 (13)	0.0547 (17)	0.0475 (14)	0.0131 (12)	0.0067 (10)	−0.0051 (11)
C16	0.0362 (11)	0.0535 (16)	0.0389 (12)	−0.0028 (11)	0.0077 (9)	−0.0074 (10)
C14	0.0480 (13)	0.0581 (18)	0.0406 (13)	−0.0057 (12)	0.0134 (10)	0.0014 (11)
C5	0.0351 (12)	0.0601 (19)	0.0543 (15)	−0.0031 (11)	0.0115 (10)	−0.0075 (12)
C9	0.0433 (13)	0.0505 (16)	0.0457 (14)	−0.0002 (11)	0.0024 (10)	0.0003 (11)
C6	0.0445 (12)	0.0390 (14)	0.0526 (14)	−0.0074 (11)	0.0183 (10)	−0.0017 (10)
C12	0.0586 (15)	0.0392 (15)	0.0426 (14)	−0.0036 (12)	0.0059 (10)	0.0004 (10)
C15	0.0482 (13)	0.0498 (17)	0.0525 (15)	−0.0062 (12)	0.0120 (11)	−0.0074 (12)
C11	0.072 (3)	0.045 (2)	0.041 (2)	−0.013 (2)	0.0011 (19)	−0.0076 (16)
C10	0.097 (2)	0.069 (2)	0.0436 (16)	−0.0073 (19)	−0.0093 (14)	−0.0045 (13)
C11A	0.070 (8)	0.056 (7)	0.066 (7)	−0.004 (6)	0.007 (6)	−0.012 (6)

Geometric parameters (Å, º) top

S1—N1	1.5963 (19)	C16—C15	1.509 (4)
S1—C1	1.772 (2)	C14—H14A	0.9700
S1—O1	1.4412 (19)	C14—H14B	0.9700
S1—O2	1.4352 (17)	C5—H5	0.9300
N2—C7	1.338 (3)	C5—C6	1.379 (3)
N2—C13	1.459 (3)	C9—H9A	0.9700
N2—C16	1.473 (3)	C9—H9B	0.9700
N1—C7	1.326 (3)	C9—C10	1.523 (4)
C1—C2	1.382 (3)	C6—H6	0.9300
C1—C6	1.385 (3)	C12—H12A	0.9700
C7—C8	1.517 (3)	C12—H12B	0.9700
C8—C9	1.551 (3)	C12—H12C	0.9700
C8—C12	1.540 (3)	C12—H12D	0.9700
C8—H8	0.94 (2)	C12—C11	1.537 (5)
O3—C14	1.415 (3)	C12—C11A	1.545 (17)
O3—C15	1.416 (3)	C15—H15A	0.9700
F8—C4	1.356 (3)	C15—H15B	0.9700
C2—H2	0.9300	C11—H11A	0.9700
C2—C3	1.373 (3)	C11—H11B	0.9700
C13—H13A	0.9700	C11—C10	1.483 (5)
C13—H13B	0.9700	C10—H10A	0.9700
C13—C14	1.505 (3)	C10—H10B	0.9700
C3—H3	0.9300	C10—H10C	0.9700
C3—C4	1.365 (3)	C10—H10D	0.9700
C4—C5	1.365 (4)	C10—C11A	1.353 (17)
C16—H16A	0.9700	C11A—H11C	0.9700
C16—H16B	0.9700	C11A—H11D	0.9700

N1—S1—C1	106.04 (10)	C5—C6—H6	119.7
O1—S1—N1	114.06 (11)	C8—C12—H12A	111.2
O1—S1—C1	107.44 (10)	C8—C12—H12B	111.2
O2—S1—N1	105.80 (10)	C8—C12—H12C	110.9
O2—S1—C1	107.26 (11)	C8—C12—H12D	110.9
O2—S1—O1	115.66 (12)	C8—C12—C11A	104.3 (7)
C7—N2—C13	126.79 (18)	H12A—C12—H12B	109.1
C7—N2—C16	121.98 (18)	H12A—C12—H12C	129.0
C13—N2—C16	111.13 (17)	H12A—C12—H12D	27.3
C7—N1—S1	124.71 (16)	H12B—C12—H12C	26.8
C2—C1—S1	120.31 (16)	H12B—C12—H12D	84.7
C2—C1—C6	119.8 (2)	H12C—C12—H12D	108.9
C6—C1—S1	119.90 (18)	C11—C12—C8	103.1 (2)
N2—C7—C8	119.76 (18)	C11—C12—H12A	111.2
N1—C7—N2	115.94 (19)	C11—C12—H12B	111.2
N1—C7—C8	124.3 (2)	C11—C12—H12C	85.7
C7—C8—C9	116.42 (19)	C11—C12—H12D	134.0
C7—C8—C12	115.96 (18)	C11—C12—C11A	28.2 (5)
C7—C8—H8	105.0 (12)	C11A—C12—H12A	85.0
C9—C8—H8	104.4 (12)	C11A—C12—H12B	132.7
C12—C8—C9	106.34 (18)	C11A—C12—H12C	110.9
C12—C8—H8	107.9 (14)	C11A—C12—H12D	110.9
C14—O3—C15	109.61 (17)	O3—C15—C16	111.6 (2)
C1—C2—H2	120.0	O3—C15—H15A	109.3
C3—C2—C1	120.0 (2)	O3—C15—H15B	109.3
C3—C2—H2	120.0	C16—C15—H15A	109.3
N2—C13—H13A	109.7	C16—C15—H15B	109.3
N2—C13—H13B	109.7	H15A—C15—H15B	108.0
N2—C13—C14	109.7 (2)	C12—C11—H11A	110.9
H13A—C13—H13B	108.2	C12—C11—H11B	110.9
C14—C13—H13A	109.7	H11A—C11—H11B	108.9
C14—C13—H13B	109.7	C10—C11—C12	104.4 (3)
C2—C3—H3	120.6	C10—C11—H11A	110.9
C4—C3—C2	118.7 (2)	C10—C11—H11B	110.9
C4—C3—H3	120.6	C9—C10—H10A	110.0
F8—C4—C3	118.3 (3)	C9—C10—H10B	110.0
F8—C4—C5	118.5 (2)	C9—C10—H10C	109.7
C3—C4—C5	123.2 (2)	C9—C10—H10D	109.7
N2—C16—H16A	109.7	C11—C10—C9	108.5 (3)
N2—C16—H16B	109.7	C11—C10—H10A	110.0
N2—C16—C15	109.63 (18)	C11—C10—H10B	110.0
H16A—C16—H16B	108.2	C11—C10—H10C	82.6
C15—C16—H16A	109.7	C11—C10—H10D	133.4
C15—C16—H16B	109.7	H10A—C10—H10B	108.4
O3—C14—C13	112.12 (18)	H10A—C10—H10C	29.8
O3—C14—H14A	109.2	H10A—C10—H10D	80.6
O3—C14—H14B	109.2	H10B—C10—H10C	131.2
C13—C14—H14A	109.2	H10B—C10—H10D	30.4
C13—C14—H14B	109.2	H10C—C10—H10D	108.2
H14A—C14—H14B	107.9	C11A—C10—C9	110.0 (7)
C4—C5—H5	121.1	C11A—C10—C11	30.3 (7)
C4—C5—C6	117.8 (2)	C11A—C10—H10A	131.7
C6—C5—H5	121.1	C11A—C10—H10B	81.7
C8—C9—H9A	110.8	C11A—C10—H10C	109.7
C8—C9—H9B	110.8	C11A—C10—H10D	109.7
H9A—C9—H9B	108.9	C12—C11A—H11C	109.5
C10—C9—C8	104.7 (2)	C12—C11A—H11D	109.5
C10—C9—H9A	110.8	C10—C11A—C12	110.7 (11)
C10—C9—H9B	110.8	C10—C11A—H11C	109.5
C1—C6—H6	119.7	C10—C11A—H11D	109.5
C5—C6—C1	120.6 (2)	H11C—C11A—H11D	108.1

S1—N1—C7—N2	173.72 (17)	C2—C1—C6—C5	−0.3 (3)
S1—N1—C7—C8	−5.4 (3)	C2—C3—C4—F8	−179.0 (2)
S1—C1—C2—C3	−178.33 (18)	C2—C3—C4—C5	1.0 (4)
S1—C1—C6—C5	178.44 (17)	O2—S1—N1—C7	−176.12 (19)
N2—C7—C8—C9	−59.1 (3)	O2—S1—C1—C2	75.1 (2)
N2—C7—C8—C12	67.2 (3)	O2—S1—C1—C6	−103.6 (2)
N2—C13—C14—O3	57.2 (3)	C13—N2—C7—N1	174.8 (2)
N2—C16—C15—O3	−57.1 (2)	C13—N2—C7—C8	−6.0 (3)
N1—S1—C1—C2	−37.6 (2)	C13—N2—C16—C15	54.2 (2)
N1—S1—C1—C6	143.67 (18)	C3—C4—C5—C6	−0.9 (4)
N1—C7—C8—C9	120.0 (2)	C4—C5—C6—C1	0.5 (4)
N1—C7—C8—C12	−113.8 (2)	C16—N2—C7—N1	−1.2 (3)
C1—S1—N1—C7	−62.4 (2)	C16—N2—C7—C8	177.91 (19)
C1—C2—C3—C4	−0.7 (4)	C16—N2—C13—C14	−54.0 (2)
C7—N2—C13—C14	129.6 (2)	C14—O3—C15—C16	59.7 (2)
C7—N2—C16—C15	−129.2 (2)	C9—C8—C12—C11	−28.7 (3)
C7—C8—C9—C10	141.5 (2)	C9—C8—C12—C11A	0.3 (7)
C7—C8—C12—C11	−159.9 (3)	C9—C10—C11A—C12	20.5 (12)
C7—C8—C12—C11A	−130.8 (7)	C6—C1—C2—C3	0.4 (4)
O1—S1—N1—C7	55.6 (2)	C12—C8—C9—C10	10.5 (3)
O1—S1—C1—C2	−159.96 (18)	C12—C11—C10—C9	−30.9 (4)
O1—S1—C1—C6	21.3 (2)	C12—C11—C10—C11A	67.4 (15)
C8—C9—C10—C11	12.6 (4)	C15—O3—C14—C13	−59.8 (3)
C8—C9—C10—C11A	−19.4 (8)	C11—C12—C11A—C10	78.1 (15)
C8—C12—C11—C10	36.4 (4)	C11—C10—C11A—C12	−72.0 (15)
C8—C12—C11A—C10	−12.9 (12)	C11A—C12—C11—C10	−59.6 (15)
F8—C4—C5—C6	179.1 (2)

Experimental details

Crystal data
Chemical formula	C₁₆H₂₁FN₂O₃S
M_r	340.41
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	11.5613 (7), 16.4245 (13), 8.8730 (6)
β (°)	107.768 (6)
V (Å³)	1604.5 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.25 × 0.17 × 0.03

Data collection
Diffractometer	Agilent Xcalibur, Eos
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2013)
T_min, T_max	0.939, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	6974, 3391, 2323
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.641

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.137, 1.01
No. of reflections	3391
No. of parameters	221
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.38

Computer programs: CrysAlis PRO (Agilent, 2013), SHELXS (Sheldrick, 2008), SHELXL (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Acknowledgements

This work was supported by RFBR (14–03-01033).

References

Agilent (2013). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England. Google Scholar
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
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xie, S., Lopez, S. A., Ramström, O., Yan, M. & Houk, K. N. (2015). J. Am. Chem. Soc. 137, 2958–2966. CrossRef CAS PubMed Google Scholar
Xu, X., Li, X., Ma, L., Ye, N. & Weng, B. (2008). J. Am. Chem. Soc. 130, 14048–14049. CrossRef PubMed CAS Google Scholar

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