

Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314616000134/hb4006sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2414314616000134/hb4006Isup2.hkl |
![]() | Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314616000134/hb4006Isup3.cml |
CCDC reference: 1445312
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean
(C-C) = 0.004 Å
- Disorder in main residue
- R factor = 0.046
- wR factor = 0.137
- Data-to-parameter ratio = 15.3
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.953 Note
Alert level C PLAT241_ALERT_2_C High 'MainMol' Ueq as Compared to Neighbors of C10 Check PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 Note C16 H21 F N2 O3 S
Alert level G PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ... 1 Report PLAT005_ALERT_5_G No Embedded Refinement Details found in the CIF Please Do ! PLAT300_ALERT_4_G Atom Site Occupancy of >C11 is Constrained at 0.75 Check PLAT300_ALERT_4_G Atom Site Occupancy of <C11A is Constrained at 0.25 Check PLAT300_ALERT_4_G Atom Site Occupancy of >H10A is Constrained at 0.75 Check PLAT300_ALERT_4_G Atom Site Occupancy of >H10B is Constrained at 0.75 Check PLAT300_ALERT_4_G Atom Site Occupancy of >H11A is Constrained at 0.75 Check PLAT300_ALERT_4_G Atom Site Occupancy of >H11B is Constrained at 0.75 Check PLAT300_ALERT_4_G Atom Site Occupancy of >H12A is Constrained at 0.75 Check PLAT300_ALERT_4_G Atom Site Occupancy of >H12B is Constrained at 0.75 Check PLAT300_ALERT_4_G Atom Site Occupancy of <H10C is Constrained at 0.25 Check PLAT300_ALERT_4_G Atom Site Occupancy of <H10D is Constrained at 0.25 Check PLAT300_ALERT_4_G Atom Site Occupancy of <H11C is Constrained at 0.25 Check PLAT300_ALERT_4_G Atom Site Occupancy of <H11D is Constrained at 0.25 Check PLAT300_ALERT_4_G Atom Site Occupancy of <H12C is Constrained at 0.25 Check PLAT300_ALERT_4_G Atom Site Occupancy of <H12D is Constrained at 0.25 Check PLAT301_ALERT_3_G Main Residue Disorder ............ Percentage = 4 Note PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... # 70 Check H12A -C12 -H12D 1.555 1.555 1.555 27.30 Deg. PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... # 71 Check H12B -C12 -H12C 1.555 1.555 1.555 26.80 Deg. PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... # 79 Check C11 -C12 -C11A 1.555 1.555 1.555 28.20 Deg. PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... # 106 Check H10A -C10 -H10C 1.555 1.555 1.555 29.80 Deg. PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... # 109 Check H10B -C10 -H10D 1.555 1.555 1.555 30.40 Deg. PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... # 112 Check C11A -C10 -C11 1.555 1.555 1.555 30.30 Deg. PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 6 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 1 ALERT level B = A potentially serious problem, consider carefully 2 ALERT level C = Check. Ensure it is not caused by an omission or oversight 24 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 21 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
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.
Crystal data, data collection and structure refinement details are summarized in Table 1.
The title compound is illustrated in Fig. 1. For background to sulfonamides, see: Xu et al. (2008); Xie et al. (2015).
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).
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).