organic compounds
(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
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
Structure description
The title compound is illustrated in Fig. 1. For background to see: Xu et al. (2008); Xie et al. (2015).
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.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 1Structural data
CCDC reference: 1445312
10.1107/S2414314616000134/hb4006sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616000134/hb4006Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314616000134/hb4006Isup3.cml
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.
The title compound is illustrated in Fig. 1. For background to
see: Xu et al. (2008); Xie et al. (2015).Data collection: CrysAlis PRO (Agilent, 2013); cell
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).C16H21FN2O3S | F(000) = 720 |
Mr = 340.41 | Dx = 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 |
Agilent Xcalibur, Eos diffractometer | 3391 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2323 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
Detector resolution: 15.9555 pixels mm-1 | θmax = 27.1°, θmin = 2.2° |
ω scans | h = −9→14 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | k = −21→18 |
Tmin = 0.939, Tmax = 1.000 | l = −10→11 |
6974 measured reflections |
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(Fo2) + (0.075P)2 + 0.010P] where P = (Fo2 + 2Fc2)/3 |
3391 reflections | (Δ/σ)max < 0.001 |
221 parameters | Δρmax = 0.29 e Å−3 |
6 restraints | Δρmin = −0.38 e Å−3 |
C16H21FN2O3S | V = 1604.5 (2) Å3 |
Mr = 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)° |
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 = 1.000 | Rint = 0.029 |
6974 measured reflections |
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 | Δρmax = 0.29 e Å−3 |
3391 reflections | Δρmin = −0.38 e Å−3 |
221 parameters |
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. |
x | y | z | Uiso*/Ueq | 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 |
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) |
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 |
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) |
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) |
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 (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 |
Δρmax, Δρmin (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
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