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The title compound, C
18H
14F
4N
2O
2S, crystallizes in a conformation where the two benzene rings are parallel. In the crystal structure, molecules form one-dimensional extended chains
via O—H
N hydrogen bonds.
Supporting information
CCDC reference: 625035
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.004 Å
- Disorder in main residue
- R factor = 0.065
- wR factor = 0.175
- Data-to-parameter ratio = 16.3
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.73 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.25 Ratio
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for S1
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C9
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11
PLAT301_ALERT_3_C Main Residue Disorder ......................... 4.00 Perc.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C13 - C14 ... 1.35 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C14 - C15 ... 1.35 Ang.
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C8 - C17 ... 1.44 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H111 .. O1 .. 2.62 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
10 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
7 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.
N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-(4-fluorophenylsulfanyl)-2-hydroxy- 2-methylpropionamide
top
Crystal data top
C18H14F4N2O2S | Z = 2 |
Mr = 398.37 | F(000) = 408.00 |
Triclinic, P1 | Dx = 1.456 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.7107 Å |
a = 10.136 (5) Å | Cell parameters from 7424 reflections |
b = 10.343 (6) Å | θ = 3.3–27.5° |
c = 10.524 (4) Å | µ = 0.23 mm−1 |
α = 106.82 (2)° | T = 296 K |
β = 116.97 (2)° | Block, colorless |
γ = 95.19 (2)° | 0.28 × 0.25 × 0.17 mm |
V = 908.9 (8) Å3 | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | Rint = 0.026 |
Detector resolution: 10.00 pixels mm-1 | θmax = 27.5° |
ω scans | h = −12→13 |
9009 measured reflections | k = −13→13 |
4135 independent reflections | l = −12→13 |
2814 reflections with F2 > 2σ(F2) | |
Refinement top
Refinement on F2 | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.065 | w = 1/[0.0015Fo2 + 3σ(Fo2) + 0.5]/(4Fo2) |
wR(F2) = 0.175 | (Δ/σ)max < 0.001 |
S = 1.01 | Δρmax = 0.31 e Å−3 |
4135 reflections | Δρmin = −0.35 e Å−3 |
253 parameters | |
Special details top
Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY |
Refinement. Refinement using all reflections. The weighted R-factor (wR) and
goodness of fit (S) are based on F2. R-factor (gt) are
based on F. The threshold expression of F2 > 2.0
σ(F2) is used only for calculating R-factor (gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
S1 | 1.05362 (9) | 0.66265 (11) | 0.81085 (8) | 0.0713 (2) | |
F1 | 0.3255 (2) | 0.0045 (2) | 0.7624 (3) | 0.1071 (9) | |
F2 | 0.5424 (3) | 0.0978 (2) | 0.9456 (2) | 0.1414 (9) | |
F3 | 0.5039 (4) | −0.0695 (2) | 0.7535 (4) | 0.1452 (15) | |
F41 | 0.6412 (12) | 0.5005 (16) | 0.1544 (5) | 0.136 (4) | 0.40 |
F42 | 0.6827 (11) | 0.5636 (12) | 0.1553 (5) | 0.125 (2) | 0.60 |
O1 | 0.9926 (2) | 0.66885 (18) | 1.07295 (18) | 0.0498 (4) | |
O2 | 0.6598 (2) | 0.6361 (2) | 0.73183 (19) | 0.0501 (5) | |
N1 | 0.7433 (2) | 0.4881 (2) | 0.8566 (2) | 0.0444 (5) | |
N2 | 0.1879 (3) | −0.1128 (2) | 0.3768 (2) | 0.0750 (8) | |
C1 | 0.9806 (3) | 0.7893 (2) | 0.9050 (2) | 0.0511 (7) | |
C2 | 0.8971 (2) | 0.7284 (2) | 0.9706 (2) | 0.0399 (6) | |
C3 | 0.8414 (3) | 0.8390 (3) | 1.0513 (3) | 0.0563 (8) | |
C4 | 0.7544 (2) | 0.6118 (2) | 0.8398 (2) | 0.0394 (6) | |
C5 | 0.6233 (2) | 0.3660 (2) | 0.7574 (2) | 0.0385 (5) | |
C6 | 0.5300 (2) | 0.3381 (2) | 0.6010 (2) | 0.0407 (6) | |
C7 | 0.4200 (2) | 0.2130 (2) | 0.5089 (2) | 0.0417 (6) | |
C8 | 0.3984 (2) | 0.1153 (2) | 0.5687 (2) | 0.0396 (6) | |
C9 | 0.4899 (2) | 0.1449 (2) | 0.7264 (2) | 0.0397 (6) | |
C10 | 0.6005 (2) | 0.2696 (2) | 0.8181 (2) | 0.0401 (6) | |
C11 | 0.9317 (3) | 0.6279 (3) | 0.6132 (2) | 0.0559 (8) | |
C12 | 0.8210 (3) | 0.5040 (4) | 0.5210 (3) | 0.0717 (10) | |
C13 | 0.7309 (4) | 0.4758 (5) | 0.3624 (4) | 0.0963 (13) | |
C14 | 0.7559 (5) | 0.5720 (7) | 0.3070 (3) | 0.1053 (18) | |
C15 | 0.8668 (6) | 0.6932 (6) | 0.3956 (5) | 0.1030 (18) | |
C16 | 0.9555 (4) | 0.7216 (4) | 0.5500 (4) | 0.0758 (12) | |
C17 | 0.2817 (3) | −0.0134 (2) | 0.4641 (2) | 0.0514 (7) | |
C18 | 0.4695 (3) | 0.0451 (2) | 0.7974 (2) | 0.0990 (13) | |
H1 | 0.9107 | 0.8231 | 0.8302 | 0.061* | |
H2 | 1.0664 | 0.8668 | 0.9878 | 0.061* | |
H6 | 0.5435 | 0.4071 | 0.5578 | 0.049* | |
H7 | 0.3553 | 0.1923 | 0.3988 | 0.050* | |
H10 | 0.6641 | 0.2907 | 0.9284 | 0.048* | |
H12 | 0.8069 | 0.4371 | 0.5662 | 0.086* | |
H13 | 0.6518 | 0.3875 | 0.2938 | 0.115* | |
H15 | 0.8811 | 0.7587 | 0.3490 | 0.124* | |
H16 | 1.0361 | 0.8093 | 0.6171 | 0.091* | |
H31 | 0.7912 | 0.7982 | 1.0942 | 0.067* | |
H32 | 0.9276 | 0.9153 | 1.1319 | 0.067* | |
H33 | 0.7708 | 0.8728 | 0.9787 | 0.067* | |
H101 | 1.0521 | 0.7372 | 1.1696 | 0.060* | |
H111 | 0.8171 | 0.4834 | 0.9375 | 0.053* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0565 (4) | 0.1081 (7) | 0.0483 (4) | 0.0362 (4) | 0.0218 (3) | 0.0308 (4) |
F1 | 0.0872 (15) | 0.126 (2) | 0.1361 (19) | 0.0082 (14) | 0.0656 (14) | 0.0755 (17) |
F2 | 0.191 (2) | 0.1093 (19) | 0.0545 (11) | −0.0607 (18) | 0.0182 (14) | 0.0413 (12) |
F3 | 0.268 (4) | 0.1039 (19) | 0.209 (3) | 0.115 (2) | 0.186 (3) | 0.120 (2) |
F41 | 0.108 (7) | 0.240 (15) | 0.037 (3) | 0.104 (8) | 0.022 (3) | 0.029 (4) |
F42 | 0.114 (4) | 0.212 (8) | 0.056 (2) | 0.064 (4) | 0.040 (2) | 0.059 (3) |
O1 | 0.0529 (10) | 0.0367 (9) | 0.0320 (8) | 0.0082 (8) | 0.0010 (7) | 0.0110 (7) |
O2 | 0.0440 (9) | 0.0500 (11) | 0.0439 (9) | 0.0111 (8) | 0.0072 (7) | 0.0264 (8) |
N1 | 0.0429 (11) | 0.0373 (11) | 0.0316 (9) | 0.0007 (9) | 0.0016 (7) | 0.0166 (8) |
N2 | 0.0672 (17) | 0.0586 (17) | 0.0528 (14) | −0.0070 (14) | 0.0082 (12) | 0.0034 (12) |
C1 | 0.0493 (15) | 0.0424 (15) | 0.0453 (13) | 0.0019 (12) | 0.0131 (11) | 0.0159 (11) |
C2 | 0.0440 (13) | 0.0337 (13) | 0.0333 (11) | 0.0112 (10) | 0.0110 (9) | 0.0149 (9) |
C3 | 0.0659 (18) | 0.0474 (16) | 0.0529 (15) | 0.0220 (14) | 0.0281 (13) | 0.0159 (12) |
C4 | 0.0421 (13) | 0.0375 (13) | 0.0326 (11) | 0.0088 (10) | 0.0130 (9) | 0.0154 (9) |
C5 | 0.0369 (12) | 0.0370 (13) | 0.0305 (10) | 0.0054 (10) | 0.0083 (8) | 0.0138 (9) |
C6 | 0.0402 (12) | 0.0431 (14) | 0.0323 (11) | 0.0096 (11) | 0.0106 (9) | 0.0186 (10) |
C7 | 0.0354 (12) | 0.0485 (15) | 0.0285 (10) | 0.0108 (11) | 0.0078 (8) | 0.0115 (10) |
C8 | 0.0320 (11) | 0.0390 (13) | 0.0350 (11) | 0.0071 (10) | 0.0096 (9) | 0.0097 (9) |
C9 | 0.0370 (12) | 0.0415 (14) | 0.0376 (11) | 0.0084 (10) | 0.0160 (9) | 0.0158 (10) |
C10 | 0.0384 (12) | 0.0409 (13) | 0.0292 (10) | 0.0059 (10) | 0.0077 (8) | 0.0144 (9) |
C11 | 0.0456 (15) | 0.079 (2) | 0.0445 (13) | 0.0195 (15) | 0.0221 (11) | 0.0242 (14) |
C12 | 0.0561 (18) | 0.085 (2) | 0.0710 (19) | 0.0174 (18) | 0.0369 (15) | 0.0170 (17) |
C13 | 0.053 (2) | 0.123 (3) | 0.068 (2) | 0.025 (2) | 0.0230 (17) | −0.010 (2) |
C14 | 0.090 (3) | 0.185 (5) | 0.050 (2) | 0.081 (3) | 0.035 (2) | 0.043 (2) |
C15 | 0.126 (3) | 0.159 (4) | 0.071 (2) | 0.077 (3) | 0.062 (2) | 0.072 (2) |
C16 | 0.080 (2) | 0.094 (2) | 0.072 (2) | 0.031 (2) | 0.0452 (18) | 0.041 (2) |
C17 | 0.0481 (15) | 0.0477 (16) | 0.0380 (12) | 0.0044 (13) | 0.0101 (11) | 0.0108 (11) |
C18 | 0.104 (2) | 0.099 (2) | 0.085 (2) | 0.007 (2) | 0.042 (2) | 0.038 (2) |
Geometric parameters (Å, º) top
S1—C1 | 1.826 (3) | C9—C18 | 1.488 (4) |
S1—C11 | 1.772 (2) | C11—C12 | 1.369 (4) |
F1—C18 | 1.324 (4) | C11—C16 | 1.384 (6) |
F2—C18 | 1.291 (3) | C12—C13 | 1.411 (5) |
F3—C18 | 1.283 (4) | C13—C14 | 1.349 (9) |
F41—C14 | 1.393 (6) | C14—C15 | 1.349 (7) |
F42—C14 | 1.393 (7) | C15—C16 | 1.373 (5) |
O1—C2 | 1.422 (3) | O1—H101 | 0.921 |
O2—C4 | 1.223 (3) | N1—H111 | 0.860 |
N1—C4 | 1.343 (3) | C1—H1 | 0.970 |
N1—C5 | 1.404 (2) | C1—H2 | 0.970 |
N2—C17 | 1.135 (3) | C3—H31 | 0.960 |
C1—C2 | 1.508 (4) | C3—H32 | 0.960 |
C2—C3 | 1.529 (4) | C3—H33 | 0.960 |
C2—C4 | 1.536 (2) | C6—H6 | 0.980 |
C5—C6 | 1.397 (3) | C7—H7 | 0.980 |
C5—C10 | 1.383 (4) | C10—H10 | 0.980 |
C6—C7 | 1.375 (3) | C12—H12 | 0.980 |
C7—C8 | 1.385 (4) | C13—H13 | 0.980 |
C8—C9 | 1.403 (3) | C15—H15 | 0.980 |
C8—C17 | 1.439 (3) | C16—H16 | 0.980 |
C9—C10 | 1.374 (2) | | |
| | | |
S1···F41i | 3.582 (14) | C5···H101ix | 3.372 |
S1···C13i | 3.580 (5) | C6···H6vii | 3.474 |
S1···C14i | 3.526 (6) | C7···H1vii | 3.502 |
F1···F2ii | 3.280 (4) | C8···H15vii | 3.566 |
F1···C3iii | 3.317 (5) | C10···H101ix | 3.472 |
F2···F1ii | 3.280 (4) | C11···H7vii | 3.566 |
F2···F2ii | 2.838 (4) | C13···H6vii | 3.471 |
F2···F3ii | 3.492 (6) | C15···H12i | 3.582 |
F2···C18ii | 3.477 (4) | C15···H31viii | 3.431 |
F3···F2ii | 3.492 (6) | C16···H7vii | 3.574 |
F3···O2iv | 3.552 (4) | C16···H12i | 3.495 |
F3···C7v | 3.191 (5) | C17···H32xiii | 3.506 |
F41···S1i | 3.582 (14) | C17···H101xiii | 3.069 |
F41···F41vi | 3.208 (12) | H1···C7vii | 3.502 |
F41···F42vi | 3.239 (10) | H1···H2xv | 3.150 |
F41···C5vii | 3.484 (14) | H1···H7vii | 2.629 |
F41···C10viii | 3.466 (9) | H1···H32xv | 2.854 |
F42···F41vi | 3.239 (10) | H2···C1xv | 3.554 |
F42···F42vi | 3.433 (10) | H2···C3xv | 3.296 |
F42···N1viii | 3.359 (9) | H2···H1xv | 3.150 |
O1···O1ix | 3.432 (2) | H2···H2xv | 3.171 |
O1···N1ix | 3.167 (3) | H2···H10ix | 3.216 |
O1···N2x | 2.918 (2) | H2···H32xv | 2.891 |
O1···C5ix | 3.577 (3) | H2···H33xv | 2.867 |
O2···F3xi | 3.552 (4) | H6···O2vii | 2.662 |
O2···C6vii | 3.250 (3) | H6···C6vii | 3.474 |
O2···C7vii | 3.188 (3) | H6···C13vii | 3.471 |
O2···C13vii | 3.599 (4) | H6···H6vii | 2.577 |
N1···F42xii | 3.359 (9) | H6···H13vii | 3.538 |
N1···O1ix | 3.167 (3) | H7···F3v | 2.728 |
N2···O1xiii | 2.918 (2) | H7···O2vii | 2.516 |
N2···C3xiii | 3.478 (3) | H7···C1vii | 3.527 |
C3···F1iii | 3.317 (5) | H7···C4vii | 3.530 |
C3···N2x | 3.478 (3) | H7···C11vii | 3.566 |
C5···F41vii | 3.484 (14) | H7···C16vii | 3.574 |
C5···O1ix | 3.577 (3) | H7···H1vii | 2.629 |
C6···O2vii | 3.250 (3) | H7···H33vii | 3.400 |
C6···C13vii | 3.502 (6) | H10···S1ix | 2.795 |
C6···C14vii | 3.566 (6) | H10···F41xii | 2.833 |
C7···F3v | 3.191 (5) | H10···F42xii | 3.050 |
C7···O2vii | 3.188 (3) | H10···O1ix | 3.474 |
C8···C15vii | 3.569 (7) | H10···C1ix | 3.519 |
C10···F41xii | 3.466 (9) | H10···H2ix | 3.216 |
C10···F42vii | 3.556 (12) | H10···H101ix | 3.477 |
C11···C12i | 3.585 (5) | H12···N2v | 3.575 |
C11···C13i | 3.597 (6) | H12···C15i | 3.582 |
C12···C11i | 3.585 (5) | H12···C16i | 3.495 |
C12···C16i | 3.553 (6) | H12···H101ix | 3.575 |
C13···S1i | 3.580 (5) | H13···F3v | 3.310 |
C13···O2vii | 3.599 (4) | H13···O2vii | 3.026 |
C13···C6vii | 3.502 (5) | H13···H6vii | 3.538 |
C13···C11i | 3.597 (6) | H15···F1vii | 3.481 |
C14···S1i | 3.526 (6) | H15···O1viii | 3.491 |
C14···C6vii | 3.566 (6) | H15···N2xvi | 3.118 |
C15···C8vii | 3.569 (7) | H15···C3viii | 3.331 |
C16···C12i | 3.553 (6) | H15···C8vii | 3.566 |
C18···F2ii | 3.477 (4) | H15···H31viii | 2.583 |
S1···H10ix | 2.795 | H15···H32viii | 3.324 |
S1···H111ix | 3.246 | H15···H101viii | 3.068 |
F1···H15vii | 3.481 | H16···F1xvi | 2.845 |
F1···H16xiv | 2.845 | H16···H32xv | 3.130 |
F1···H31iii | 2.849 | H31···F1iii | 2.849 |
F1···H32iii | 3.309 | H31···F2iii | 3.522 |
F1···H33iii | 3.259 | H31···F42xii | 2.927 |
F2···H31iii | 3.522 | H31···N2x | 3.572 |
F2···H33iv | 3.407 | H31···C15xii | 3.431 |
F3···H7v | 2.728 | H31···H15xii | 2.583 |
F3···H13v | 3.310 | H32···F1iii | 3.309 |
F3···H33iv | 2.930 | H32···N2x | 2.845 |
F41···H10viii | 2.833 | H32···C1xv | 3.294 |
F41···H111viii | 3.455 | H32···C17x | 3.506 |
F42···H10viii | 3.050 | H32···H1xv | 2.854 |
F42···H31viii | 2.927 | H32···H2xv | 2.891 |
F42···H111viii | 3.119 | H32···H15xii | 3.324 |
O1···H10ix | 3.474 | H32···H16xv | 3.130 |
O1···H15xii | 3.491 | H33···F1iii | 3.259 |
O1···H111ix | 2.618 | H33···F2xi | 3.407 |
O2···H6vii | 2.662 | H33···F3xi | 2.930 |
O2···H7vii | 2.516 | H33···H2xv | 2.867 |
O2···H13vii | 3.026 | H33···H7vii | 3.400 |
N1···H101ix | 3.290 | H101···N1ix | 3.290 |
N2···H12v | 3.575 | H101···N2x | 1.997 |
N2···H15xiv | 3.118 | H101···C5ix | 3.372 |
N2···H31xiii | 3.572 | H101···C10ix | 3.472 |
N2···H32xiii | 2.845 | H101···C17x | 3.069 |
N2···H101xiii | 1.997 | H101···H10ix | 3.477 |
C1···H2xv | 3.554 | H101···H12ix | 3.575 |
C1···H7vii | 3.527 | H101···H15xii | 3.068 |
C1···H10ix | 3.519 | H101···H111ix | 2.941 |
C1···H32xv | 3.294 | H111···S1ix | 3.246 |
C3···H2xv | 3.296 | H111···F41xii | 3.455 |
C3···H15xii | 3.331 | H111···F42xii | 3.119 |
C4···H7vii | 3.530 | H111···O1ix | 2.618 |
| | | |
C1—S1—C11 | 103.32 (15) | N2—C17—C8 | 177.1 (3) |
C4—N1—C5 | 127.09 (19) | F1—C18—F2 | 102.8 (3) |
S1—C1—C2 | 112.9 (2) | F1—C18—F3 | 104.1 (2) |
O1—C2—C1 | 110.5 (2) | F1—C18—C9 | 112.6 (2) |
O1—C2—C3 | 110.8 (2) | F2—C18—F3 | 108.7 (3) |
O1—C2—C4 | 108.0 (2) | F2—C18—C9 | 113.8 (2) |
C1—C2—C3 | 111.0 (2) | F3—C18—C9 | 113.9 (3) |
C1—C2—C4 | 109.5 (2) | C2—O1—H101 | 109.4 |
C3—C2—C4 | 107.0 (2) | C4—N1—H111 | 116.5 |
O2—C4—N1 | 124.81 (18) | C5—N1—H111 | 116.4 |
O2—C4—C2 | 119.9 (2) | S1—C1—H1 | 108.5 |
N1—C4—C2 | 115.28 (19) | S1—C1—H2 | 108.5 |
N1—C5—C6 | 122.3 (2) | C2—C1—H1 | 108.8 |
N1—C5—C10 | 118.03 (19) | C2—C1—H2 | 108.7 |
C6—C5—C10 | 119.68 (19) | H1—C1—H2 | 109.5 |
C5—C6—C7 | 119.2 (2) | C2—C3—H31 | 109.3 |
C6—C7—C8 | 121.3 (2) | C2—C3—H32 | 109.4 |
C7—C8—C9 | 119.35 (19) | C2—C3—H33 | 109.7 |
C7—C8—C17 | 117.7 (2) | H31—C3—H32 | 109.5 |
C9—C8—C17 | 122.9 (2) | H31—C3—H33 | 109.5 |
C8—C9—C10 | 119.2 (2) | H32—C3—H33 | 109.5 |
C8—C9—C18 | 121.7 (2) | C5—C6—H6 | 120.1 |
C10—C9—C18 | 119.1 (2) | C7—C6—H6 | 120.7 |
C5—C10—C9 | 121.2 (2) | C6—C7—H7 | 119.5 |
S1—C11—C12 | 119.9 (3) | C8—C7—H7 | 119.2 |
S1—C11—C16 | 119.9 (2) | C5—C10—H10 | 119.5 |
C12—C11—C16 | 120.0 (2) | C9—C10—H10 | 119.3 |
C11—C12—C13 | 118.8 (4) | C11—C12—H12 | 119.5 |
C12—C13—C14 | 119.0 (3) | C13—C12—H12 | 121.7 |
F41—C14—C13 | 97.4 (7) | C12—C13—H13 | 120.4 |
F41—C14—C15 | 139.7 (8) | C14—C13—H13 | 120.6 |
F42—C14—C13 | 128.1 (6) | C14—C15—H15 | 119.6 |
F42—C14—C15 | 108.9 (7) | C16—C15—H15 | 121.8 |
C13—C14—C15 | 123.0 (3) | C11—C16—H16 | 119.1 |
C14—C15—C16 | 118.6 (6) | C15—C16—H16 | 120.2 |
C11—C16—C15 | 120.7 (3) | | |
| | | |
C1—S1—C11—C12 | −105.5 (3) | C6—C7—C8—C17 | −179.5 (2) |
C1—S1—C11—C16 | 79.1 (3) | C7—C8—C9—C10 | −0.8 (4) |
C11—S1—C1—C2 | 108.02 (19) | C7—C8—C9—C18 | 178.7 (2) |
F42—F41—C14—C13 | −175.1 (14) | C17—C8—C9—C10 | 179.0 (2) |
F42—F41—C14—C15 | 4 (2) | C17—C8—C9—C18 | −1.5 (4) |
F41—F42—C14—C13 | 6.2 (18) | C8—C9—C10—C5 | −0.2 (4) |
F41—F42—C14—C15 | −177.0 (14) | C8—C9—C18—F1 | −51.7 (4) |
C4—N1—C5—C6 | 26.2 (4) | C8—C9—C18—F2 | −168.1 (3) |
C4—N1—C5—C10 | −155.3 (3) | C8—C9—C18—F3 | 66.6 (3) |
C5—N1—C4—O2 | −0.9 (5) | C10—C9—C18—F1 | 127.8 (2) |
C5—N1—C4—C2 | 177.9 (2) | C10—C9—C18—F2 | 11.4 (4) |
S1—C1—C2—O1 | 55.44 (19) | C10—C9—C18—F3 | −114.0 (3) |
S1—C1—C2—C3 | 178.70 (15) | C18—C9—C10—C5 | −179.7 (2) |
S1—C1—C2—C4 | −63.4 (2) | S1—C11—C12—C13 | −176.7 (3) |
O1—C2—C4—O2 | −175.2 (2) | S1—C11—C16—C15 | 176.8 (4) |
O1—C2—C4—N1 | 5.9 (3) | C12—C11—C16—C15 | 1.4 (7) |
C1—C2—C4—O2 | −54.9 (3) | C16—C11—C12—C13 | −1.2 (6) |
C1—C2—C4—N1 | 126.3 (2) | C11—C12—C13—C14 | −0.4 (7) |
C3—C2—C4—O2 | 65.5 (3) | C12—C13—C14—F41 | −178.3 (7) |
C3—C2—C4—N1 | −113.3 (3) | C12—C13—C14—F42 | 178.5 (8) |
N1—C5—C6—C7 | 176.4 (2) | C12—C13—C14—C15 | 2.0 (9) |
N1—C5—C10—C9 | −176.9 (2) | F41—C14—C15—C16 | 178.7 (11) |
C6—C5—C10—C9 | 1.6 (4) | F42—C14—C15—C16 | −178.9 (7) |
C10—C5—C6—C7 | −2.0 (4) | C13—C14—C15—C16 | −1.9 (10) |
C5—C6—C7—C8 | 1.1 (4) | C14—C15—C16—C11 | 0.1 (6) |
C6—C7—C8—C9 | 0.3 (4) | | |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y, −z+2; (iii) −x+1, −y+1, −z+2; (iv) x, y−1, z; (v) −x+1, −y, −z+1; (vi) −x+1, −y+1, −z; (vii) −x+1, −y+1, −z+1; (viii) x, y, z−1; (ix) −x+2, −y+1, −z+2; (x) x+1, y+1, z+1; (xi) x, y+1, z; (xii) x, y, z+1; (xiii) x−1, y−1, z−1; (xiv) x−1, y−1, z; (xv) −x+2, −y+2, −z+2; (xvi) x+1, y+1, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H101···N2x | 0.92 | 2.00 | 2.918 (2) | 178 |
N1—H111···O1ix | 0.86 | 2.62 | 3.167 (3) | 123 |
Symmetry codes: (ix) −x+2, −y+1, −z+2; (x) x+1, y+1, z+1. |
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