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

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ISSN: 2414-3146

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

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.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

The title compound is illustrated in Fig. 1[link]. For background to sulfonamides, see: Xu et al. (2008[Xu, X., Li, X., Ma, L., Ye, N. & Weng, B. (2008). J. Am. Chem. Soc. 130, 14048-14049.]); Xie et al. (2015[Xie, S., Lopez, S. A., Ramström, O., Yan, M. & Houk, K. N. (2015). J. Am. Chem. Soc. 137, 2958-2966.]).

[Figure 1]
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[link]). 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]
Figure 2
Reaction scheme.

Refinement

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

Table 1
Experimental details

Crystal data
Chemical formula C16H21FN2O3S
Mr 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)
V3) 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[Agilent (2013). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.])
Tmin, Tmax 0.939, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections 6974, 3391, 2323
Rint 0.029
(sin θ/λ)max−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
Δρmax, Δρmin (e Å−3) 0.29, −0.38
Computer programs: CrysAlis PRO (Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.]), SHELXS (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]).

Structural data


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.

Refinement top

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

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
[Figure 1] Fig. 1. Please provide caption, including probability level.
[Figure 2] Fig. 2. Reaction scheme.
(E)-N-[Cyclopentyl(morpholin-4-yl)methylidene]-4-fluorobenzenesulfonamide top
Crystal data top
C16H21FN2O3SF(000) = 720
Mr = 340.41Dx = 1.409 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.7107 Å
a = 11.5613 (7) ÅCell parameters from 1405 reflections
b = 16.4245 (13) Åθ = 2.8–27.0°
c = 8.8730 (6) ŵ = 0.23 mm1
β = 107.768 (6)°T = 295 K
V = 1604.5 (2) Å3Plank, colourless
Z = 40.25 × 0.17 × 0.03 mm
Data collection top
Agilent Xcalibur, Eos
diffractometer
3391 independent reflections
Radiation source: Enhance (Mo) X-ray Source2323 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
Detector resolution: 15.9555 pixels mm-1θmax = 27.1°, θmin = 2.2°
ω scansh = 914
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2013)
k = 2118
Tmin = 0.939, Tmax = 1.000l = 1011
6974 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.075P)2 + 0.010P]
where P = (Fo2 + 2Fc2)/3
3391 reflections(Δ/σ)max < 0.001
221 parametersΔρmax = 0.29 e Å3
6 restraintsΔρmin = 0.38 e Å3
Crystal data top
C16H21FN2O3SV = 1604.5 (2) Å3
Mr = 340.41Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.5613 (7) ŵ = 0.23 mm1
b = 16.4245 (13) ÅT = 295 K
c = 8.8730 (6) Å0.25 × 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)
Tmin = 0.939, Tmax = 1.000Rint = 0.029
6974 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0466 restraints
wR(F2) = 0.137H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.29 e Å3
3391 reflectionsΔρmin = 0.38 e Å3
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
xyzUiso*/UeqOcc. (<1)
S10.26452 (5)0.09127 (4)0.07277 (6)0.04217 (19)
N20.45896 (15)0.09749 (12)0.20031 (19)0.0369 (4)
N10.37106 (15)0.10138 (13)0.0054 (2)0.0413 (5)
C10.14033 (18)0.14851 (14)0.0468 (2)0.0347 (5)
C70.36523 (18)0.07661 (14)0.1498 (2)0.0352 (5)
O10.22350 (16)0.00860 (11)0.07573 (19)0.0568 (5)
C80.26032 (19)0.02854 (15)0.2575 (2)0.0381 (5)
O30.60684 (14)0.19090 (11)0.33829 (19)0.0528 (5)
F80.14638 (14)0.28150 (12)0.3150 (2)0.0788 (5)
C20.1600 (2)0.22178 (15)0.1115 (3)0.0444 (6)
H20.23880.24060.09460.053*
O20.30637 (15)0.13122 (13)0.22357 (18)0.0605 (5)
C130.4793 (2)0.07269 (15)0.3481 (2)0.0419 (6)
H13A0.40780.04500.41480.050*
H13B0.54720.03510.32590.050*
C30.0632 (2)0.26682 (16)0.2006 (3)0.0523 (6)
H30.07540.31650.24370.063*
C40.0514 (2)0.23724 (17)0.2248 (3)0.0498 (6)
C160.56120 (19)0.14650 (16)0.1027 (3)0.0437 (6)
H16A0.63360.11300.06750.052*
H16B0.54250.16650.00990.052*
C140.5058 (2)0.14643 (17)0.4328 (3)0.0489 (6)
H14A0.52160.12930.52920.059*
H14B0.43500.18150.46210.059*
C50.0748 (2)0.16534 (17)0.1626 (3)0.0503 (6)
H50.15410.14720.18010.060*
C90.1918 (2)0.06850 (17)0.4184 (3)0.0490 (6)
H9A0.11770.09460.41350.059*
H9B0.24240.10880.44770.059*
C60.0229 (2)0.12052 (15)0.0730 (3)0.0446 (6)
H60.00970.07110.02980.053*
C120.2895 (2)0.05923 (15)0.2949 (3)0.0490 (6)
H12A0.36800.06220.31310.059*0.75
H12B0.28900.09600.20960.059*0.75
H12C0.25120.09830.24340.059*0.25
H12D0.37650.06870.26070.059*0.25
C150.5838 (2)0.21732 (16)0.1983 (3)0.0509 (6)
H15A0.51350.25290.22600.061*
H15B0.65280.24840.13460.061*
C110.1861 (5)0.0793 (3)0.4464 (5)0.0564 (12)0.75
H11A0.21040.12170.50660.068*0.75
H11B0.11410.09700.42130.068*0.75
C100.1633 (3)0.0017 (2)0.5361 (3)0.0769 (10)
H10A0.07910.00110.60130.092*0.75
H10B0.21430.00160.60470.092*0.75
H10C0.07910.01790.55740.092*0.25
H10D0.17490.01570.63500.092*0.25
H80.2026 (19)0.0260 (13)0.203 (2)0.032 (5)*
C11A0.2368 (14)0.0656 (11)0.477 (2)0.067 (4)0.25
H11C0.30270.06690.52320.081*0.25
H11D0.19120.11590.50470.081*0.25
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0421 (3)0.0542 (4)0.0311 (3)0.0068 (3)0.0124 (2)0.0008 (2)
N20.0384 (9)0.0416 (12)0.0318 (10)0.0014 (8)0.0121 (7)0.0063 (8)
N10.0360 (9)0.0565 (14)0.0311 (10)0.0024 (9)0.0099 (7)0.0061 (8)
C10.0356 (11)0.0384 (13)0.0321 (11)0.0013 (9)0.0135 (8)0.0051 (9)
C70.0350 (11)0.0366 (13)0.0336 (12)0.0057 (9)0.0099 (8)0.0001 (8)
O10.0676 (11)0.0494 (12)0.0606 (11)0.0099 (9)0.0305 (9)0.0175 (8)
C80.0383 (12)0.0427 (14)0.0342 (12)0.0046 (10)0.0124 (9)0.0024 (9)
O30.0478 (9)0.0614 (12)0.0509 (10)0.0124 (8)0.0176 (7)0.0003 (8)
F80.0623 (10)0.0796 (14)0.0833 (11)0.0288 (9)0.0054 (8)0.0109 (9)
C20.0377 (12)0.0426 (15)0.0527 (14)0.0070 (11)0.0135 (10)0.0003 (11)
O20.0537 (10)0.0952 (16)0.0311 (9)0.0093 (10)0.0106 (7)0.0109 (9)
C130.0428 (12)0.0485 (15)0.0371 (13)0.0021 (10)0.0162 (9)0.0069 (10)
C30.0590 (15)0.0397 (15)0.0577 (15)0.0003 (12)0.0170 (11)0.0082 (11)
C40.0426 (13)0.0547 (17)0.0475 (14)0.0131 (12)0.0067 (10)0.0051 (11)
C160.0362 (11)0.0535 (16)0.0389 (12)0.0028 (11)0.0077 (9)0.0074 (10)
C140.0480 (13)0.0581 (18)0.0406 (13)0.0057 (12)0.0134 (10)0.0014 (11)
C50.0351 (12)0.0601 (19)0.0543 (15)0.0031 (11)0.0115 (10)0.0075 (12)
C90.0433 (13)0.0505 (16)0.0457 (14)0.0002 (11)0.0024 (10)0.0003 (11)
C60.0445 (12)0.0390 (14)0.0526 (14)0.0074 (11)0.0183 (10)0.0017 (10)
C120.0586 (15)0.0392 (15)0.0426 (14)0.0036 (12)0.0059 (10)0.0004 (10)
C150.0482 (13)0.0498 (17)0.0525 (15)0.0062 (12)0.0120 (11)0.0074 (12)
C110.072 (3)0.045 (2)0.041 (2)0.013 (2)0.0011 (19)0.0076 (16)
C100.097 (2)0.069 (2)0.0436 (16)0.0073 (19)0.0093 (14)0.0045 (13)
C11A0.070 (8)0.056 (7)0.066 (7)0.004 (6)0.007 (6)0.012 (6)
Geometric parameters (Å, º) top
S1—N11.5963 (19)C16—C151.509 (4)
S1—C11.772 (2)C14—H14A0.9700
S1—O11.4412 (19)C14—H14B0.9700
S1—O21.4352 (17)C5—H50.9300
N2—C71.338 (3)C5—C61.379 (3)
N2—C131.459 (3)C9—H9A0.9700
N2—C161.473 (3)C9—H9B0.9700
N1—C71.326 (3)C9—C101.523 (4)
C1—C21.382 (3)C6—H60.9300
C1—C61.385 (3)C12—H12A0.9700
C7—C81.517 (3)C12—H12B0.9700
C8—C91.551 (3)C12—H12C0.9700
C8—C121.540 (3)C12—H12D0.9700
C8—H80.94 (2)C12—C111.537 (5)
O3—C141.415 (3)C12—C11A1.545 (17)
O3—C151.416 (3)C15—H15A0.9700
F8—C41.356 (3)C15—H15B0.9700
C2—H20.9300C11—H11A0.9700
C2—C31.373 (3)C11—H11B0.9700
C13—H13A0.9700C11—C101.483 (5)
C13—H13B0.9700C10—H10A0.9700
C13—C141.505 (3)C10—H10B0.9700
C3—H30.9300C10—H10C0.9700
C3—C41.365 (3)C10—H10D0.9700
C4—C51.365 (4)C10—C11A1.353 (17)
C16—H16A0.9700C11A—H11C0.9700
C16—H16B0.9700C11A—H11D0.9700
N1—S1—C1106.04 (10)C5—C6—H6119.7
O1—S1—N1114.06 (11)C8—C12—H12A111.2
O1—S1—C1107.44 (10)C8—C12—H12B111.2
O2—S1—N1105.80 (10)C8—C12—H12C110.9
O2—S1—C1107.26 (11)C8—C12—H12D110.9
O2—S1—O1115.66 (12)C8—C12—C11A104.3 (7)
C7—N2—C13126.79 (18)H12A—C12—H12B109.1
C7—N2—C16121.98 (18)H12A—C12—H12C129.0
C13—N2—C16111.13 (17)H12A—C12—H12D27.3
C7—N1—S1124.71 (16)H12B—C12—H12C26.8
C2—C1—S1120.31 (16)H12B—C12—H12D84.7
C2—C1—C6119.8 (2)H12C—C12—H12D108.9
C6—C1—S1119.90 (18)C11—C12—C8103.1 (2)
N2—C7—C8119.76 (18)C11—C12—H12A111.2
N1—C7—N2115.94 (19)C11—C12—H12B111.2
N1—C7—C8124.3 (2)C11—C12—H12C85.7
C7—C8—C9116.42 (19)C11—C12—H12D134.0
C7—C8—C12115.96 (18)C11—C12—C11A28.2 (5)
C7—C8—H8105.0 (12)C11A—C12—H12A85.0
C9—C8—H8104.4 (12)C11A—C12—H12B132.7
C12—C8—C9106.34 (18)C11A—C12—H12C110.9
C12—C8—H8107.9 (14)C11A—C12—H12D110.9
C14—O3—C15109.61 (17)O3—C15—C16111.6 (2)
C1—C2—H2120.0O3—C15—H15A109.3
C3—C2—C1120.0 (2)O3—C15—H15B109.3
C3—C2—H2120.0C16—C15—H15A109.3
N2—C13—H13A109.7C16—C15—H15B109.3
N2—C13—H13B109.7H15A—C15—H15B108.0
N2—C13—C14109.7 (2)C12—C11—H11A110.9
H13A—C13—H13B108.2C12—C11—H11B110.9
C14—C13—H13A109.7H11A—C11—H11B108.9
C14—C13—H13B109.7C10—C11—C12104.4 (3)
C2—C3—H3120.6C10—C11—H11A110.9
C4—C3—C2118.7 (2)C10—C11—H11B110.9
C4—C3—H3120.6C9—C10—H10A110.0
F8—C4—C3118.3 (3)C9—C10—H10B110.0
F8—C4—C5118.5 (2)C9—C10—H10C109.7
C3—C4—C5123.2 (2)C9—C10—H10D109.7
N2—C16—H16A109.7C11—C10—C9108.5 (3)
N2—C16—H16B109.7C11—C10—H10A110.0
N2—C16—C15109.63 (18)C11—C10—H10B110.0
H16A—C16—H16B108.2C11—C10—H10C82.6
C15—C16—H16A109.7C11—C10—H10D133.4
C15—C16—H16B109.7H10A—C10—H10B108.4
O3—C14—C13112.12 (18)H10A—C10—H10C29.8
O3—C14—H14A109.2H10A—C10—H10D80.6
O3—C14—H14B109.2H10B—C10—H10C131.2
C13—C14—H14A109.2H10B—C10—H10D30.4
C13—C14—H14B109.2H10C—C10—H10D108.2
H14A—C14—H14B107.9C11A—C10—C9110.0 (7)
C4—C5—H5121.1C11A—C10—C1130.3 (7)
C4—C5—C6117.8 (2)C11A—C10—H10A131.7
C6—C5—H5121.1C11A—C10—H10B81.7
C8—C9—H9A110.8C11A—C10—H10C109.7
C8—C9—H9B110.8C11A—C10—H10D109.7
H9A—C9—H9B108.9C12—C11A—H11C109.5
C10—C9—C8104.7 (2)C12—C11A—H11D109.5
C10—C9—H9A110.8C10—C11A—C12110.7 (11)
C10—C9—H9B110.8C10—C11A—H11C109.5
C1—C6—H6119.7C10—C11A—H11D109.5
C5—C6—C1120.6 (2)H11C—C11A—H11D108.1
S1—N1—C7—N2173.72 (17)C2—C1—C6—C50.3 (3)
S1—N1—C7—C85.4 (3)C2—C3—C4—F8179.0 (2)
S1—C1—C2—C3178.33 (18)C2—C3—C4—C51.0 (4)
S1—C1—C6—C5178.44 (17)O2—S1—N1—C7176.12 (19)
N2—C7—C8—C959.1 (3)O2—S1—C1—C275.1 (2)
N2—C7—C8—C1267.2 (3)O2—S1—C1—C6103.6 (2)
N2—C13—C14—O357.2 (3)C13—N2—C7—N1174.8 (2)
N2—C16—C15—O357.1 (2)C13—N2—C7—C86.0 (3)
N1—S1—C1—C237.6 (2)C13—N2—C16—C1554.2 (2)
N1—S1—C1—C6143.67 (18)C3—C4—C5—C60.9 (4)
N1—C7—C8—C9120.0 (2)C4—C5—C6—C10.5 (4)
N1—C7—C8—C12113.8 (2)C16—N2—C7—N11.2 (3)
C1—S1—N1—C762.4 (2)C16—N2—C7—C8177.91 (19)
C1—C2—C3—C40.7 (4)C16—N2—C13—C1454.0 (2)
C7—N2—C13—C14129.6 (2)C14—O3—C15—C1659.7 (2)
C7—N2—C16—C15129.2 (2)C9—C8—C12—C1128.7 (3)
C7—C8—C9—C10141.5 (2)C9—C8—C12—C11A0.3 (7)
C7—C8—C12—C11159.9 (3)C9—C10—C11A—C1220.5 (12)
C7—C8—C12—C11A130.8 (7)C6—C1—C2—C30.4 (4)
O1—S1—N1—C755.6 (2)C12—C8—C9—C1010.5 (3)
O1—S1—C1—C2159.96 (18)C12—C11—C10—C930.9 (4)
O1—S1—C1—C621.3 (2)C12—C11—C10—C11A67.4 (15)
C8—C9—C10—C1112.6 (4)C15—O3—C14—C1359.8 (3)
C8—C9—C10—C11A19.4 (8)C11—C12—C11A—C1078.1 (15)
C8—C12—C11—C1036.4 (4)C11—C10—C11A—C1272.0 (15)
C8—C12—C11A—C1012.9 (12)C11A—C12—C11—C1059.6 (15)
F8—C4—C5—C6179.1 (2)

Experimental details

Crystal data
Chemical formulaC16H21FN2O3S
Mr340.41
Crystal system, space groupMonoclinic, P21/c
Temperature (K)295
a, b, c (Å)11.5613 (7), 16.4245 (13), 8.8730 (6)
β (°) 107.768 (6)
V3)1604.5 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.23
Crystal size (mm)0.25 × 0.17 × 0.03
Data collection
DiffractometerAgilent Xcalibur, Eos
Absorption correctionMulti-scan
(CrysAlis PRO; Agilent, 2013)
Tmin, Tmax0.939, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
6974, 3391, 2323
Rint0.029
(sin θ/λ)max1)0.641
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.137, 1.01
No. of reflections3391
No. of parameters221
No. of restraints6
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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

First citationAgilent (2013). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.  Google Scholar
First citationDolomanov, 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
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationXie, S., Lopez, S. A., Ramström, O., Yan, M. & Houk, K. N. (2015). J. Am. Chem. Soc. 137, 2958–2966.  CrossRef CAS PubMed Google Scholar
First citationXu, 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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