The title compound, C
26H
23F
2NO
3S, a polysubstituted piperidine enol, adopts a twisted half-chair conformation. The crystal structure is stabilized by N—H
F, C—H
O and weak C—H
π interactions. An intramolecular O—H
S interaction generates an
S(5) graph-set motif.
Supporting information
CCDC reference: 640318
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.008 Å
- R factor = 0.079
- wR factor = 0.279
- Data-to-parameter ratio = 13.4
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for O1 - C4 .. 7.75 su
Alert level C
RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25
Weighted R factor given 0.279
RINTA01_ALERT_3_C The value of Rint is greater than 0.10
Rint given 0.115
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.12
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT084_ALERT_2_C High R2 Value .................................. 0.28
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C55
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C51
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8
Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
8 ALERT level C = Check and explain
2 ALERT level G = General alerts; check
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
4 ALERT type 2 Indicator that the structure model may be wrong or deficient
4 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996); program(s) used to solve structure: SHELXS (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97.
(2RS,5SR,6SR)-Ethyl 2,6-bis(4-fluorophenyl)-4-hydroxy-5-phenylsulfanyl-
1,2,5,6-tetrahydropyridine-3-carboxylate
top
Crystal data top
C26H23F2NO3S | F(000) = 976 |
Mr = 467.51 | Dx = 1.338 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 18.3565 (11) Å | θ = 2–25° |
b = 5.7293 (7) Å | µ = 0.18 mm−1 |
c = 22.1286 (13) Å | T = 293 K |
β = 94.242 (18)° | Block, colourless |
V = 2320.9 (3) Å3 | 0.20 × 0.16 × 0.13 mm |
Z = 4 | |
Data collection top
Nonius MACH-3 four-circle diffractometer | 2176 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.115 |
Graphite monochromator | θmax = 25.0°, θmin = 2.1° |
ω scans | h = 0→21 |
Absorption correction: ψ scan (North et al., 1968) | k = −1→6 |
Tmin = 0.965, Tmax = 0.976 | l = −26→26 |
5106 measured reflections | 3 standard reflections every 60 min |
4074 independent 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)] = 0.079 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.279 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | w = 1/[σ2(Fo2) + (0.1375P)2 + 2.5931P] where P = (Fo2 + 2Fc2)/3 |
4074 reflections | (Δ/σ)max = 0.001 |
304 parameters | Δρmax = 0.55 e Å−3 |
0 restraints | Δρmin = −0.51 e Å−3 |
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 | Uiso*/Ueq | |
C2 | 0.1699 (3) | 0.8878 (10) | 0.3453 (2) | 0.0442 (13) | |
H2 | 0.1819 | 0.7324 | 0.3617 | 0.053* | |
C3 | 0.2088 (3) | 1.0735 (10) | 0.3850 (2) | 0.0454 (13) | |
C4 | 0.2621 (3) | 1.2118 (10) | 0.3654 (2) | 0.0458 (13) | |
C5 | 0.2929 (3) | 1.1716 (10) | 0.3045 (2) | 0.0488 (13) | |
H5 | 0.2689 | 1.2848 | 0.2764 | 0.059* | |
C6 | 0.2728 (3) | 0.9295 (10) | 0.2795 (2) | 0.0458 (13) | |
H6 | 0.2984 | 0.8093 | 0.3044 | 0.055* | |
C7 | 0.1877 (3) | 1.0940 (11) | 0.4471 (2) | 0.0540 (15) | |
C8 | 0.1241 (4) | 0.9219 (13) | 0.5245 (2) | 0.073 (2) | |
H8A | 0.0974 | 1.0650 | 0.5306 | 0.088* | |
H8B | 0.1654 | 0.9143 | 0.5545 | 0.088* | |
C9 | 0.0750 (5) | 0.7113 (15) | 0.5296 (3) | 0.101 (3) | |
H9A | 0.0387 | 0.7097 | 0.4961 | 0.152* | |
H9B | 0.0516 | 0.7193 | 0.5669 | 0.152* | |
H9C | 0.1038 | 0.5714 | 0.5290 | 0.152* | |
C21 | 0.0883 (3) | 0.9207 (9) | 0.3400 (2) | 0.0415 (12) | |
C22 | 0.0574 (3) | 1.1226 (9) | 0.3142 (2) | 0.0453 (13) | |
H22 | 0.0880 | 1.2409 | 0.3023 | 0.054* | |
C23 | −0.0169 (3) | 1.1522 (10) | 0.3060 (2) | 0.0504 (14) | |
H23 | −0.0366 | 1.2880 | 0.2885 | 0.060* | |
C24 | −0.0615 (3) | 0.9772 (10) | 0.3240 (2) | 0.0490 (14) | |
C25 | −0.0342 (3) | 0.7767 (10) | 0.3502 (2) | 0.0524 (14) | |
H25 | −0.0654 | 0.6612 | 0.3627 | 0.063* | |
C26 | 0.0406 (3) | 0.7484 (9) | 0.3578 (2) | 0.0463 (13) | |
H26 | 0.0596 | 0.6117 | 0.3753 | 0.056* | |
C51 | 0.4332 (3) | 0.9950 (11) | 0.3479 (2) | 0.0496 (14) | |
C52 | 0.4845 (3) | 0.8594 (12) | 0.3202 (3) | 0.0624 (17) | |
H52 | 0.4925 | 0.8863 | 0.2798 | 0.075* | |
C53 | 0.5235 (4) | 0.6870 (14) | 0.3514 (3) | 0.078 (2) | |
H53 | 0.5581 | 0.6006 | 0.3324 | 0.094* | |
C54 | 0.5110 (4) | 0.6437 (15) | 0.4103 (3) | 0.082 (2) | |
H54 | 0.5371 | 0.5275 | 0.4318 | 0.099* | |
C55 | 0.4593 (4) | 0.7731 (17) | 0.4381 (3) | 0.101 (3) | |
H56 | 0.4498 | 0.7407 | 0.4780 | 0.121* | |
C56 | 0.4218 (4) | 0.9489 (15) | 0.4073 (3) | 0.082 (2) | |
H36 | 0.3883 | 1.0378 | 0.4269 | 0.098* | |
C61 | 0.2885 (3) | 0.8989 (10) | 0.2135 (2) | 0.0471 (13) | |
C62 | 0.3318 (3) | 0.7199 (10) | 0.1953 (3) | 0.0531 (14) | |
H62 | 0.3540 | 0.6199 | 0.2242 | 0.064* | |
C63 | 0.3429 (4) | 0.6862 (12) | 0.1351 (3) | 0.0660 (18) | |
H63 | 0.3722 | 0.5646 | 0.1233 | 0.079* | |
C64 | 0.3106 (3) | 0.8316 (13) | 0.0937 (2) | 0.0636 (17) | |
C65 | 0.2674 (4) | 1.0156 (13) | 0.1090 (3) | 0.0692 (18) | |
H65 | 0.2461 | 1.1153 | 0.0796 | 0.083* | |
C66 | 0.2570 (3) | 1.0466 (12) | 0.1699 (3) | 0.0620 (17) | |
H66 | 0.2281 | 1.1697 | 0.1816 | 0.074* | |
F1 | −0.13491 (17) | 1.0058 (7) | 0.31601 (17) | 0.0719 (11) | |
F2 | 0.3216 (2) | 0.8027 (9) | 0.03380 (15) | 0.0949 (15) | |
N1 | 0.1935 (2) | 0.9068 (10) | 0.2834 (2) | 0.0492 (12) | |
O1 | 0.2906 (3) | 1.3996 (9) | 0.3975 (2) | 0.0852 (15) | |
H1A | 0.3294 | 1.4380 | 0.3843 | 0.128* | |
O2 | 0.2034 (3) | 1.2562 (9) | 0.48133 (18) | 0.0767 (14) | |
O3 | 0.1485 (2) | 0.9132 (7) | 0.46397 (15) | 0.0593 (11) | |
S1 | 0.39135 (8) | 1.2276 (3) | 0.30535 (7) | 0.0577 (5) | |
H1 | 0.179 (3) | 0.802 (11) | 0.258 (3) | 0.06 (2)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C2 | 0.052 (3) | 0.048 (3) | 0.035 (2) | −0.001 (3) | 0.017 (2) | 0.000 (2) |
C3 | 0.046 (3) | 0.051 (3) | 0.040 (3) | −0.002 (3) | 0.012 (2) | −0.002 (2) |
C4 | 0.050 (3) | 0.044 (3) | 0.044 (3) | 0.000 (3) | 0.005 (2) | −0.007 (3) |
C5 | 0.042 (3) | 0.057 (3) | 0.049 (3) | 0.000 (3) | 0.018 (2) | 0.009 (3) |
C6 | 0.050 (3) | 0.047 (3) | 0.043 (3) | −0.003 (3) | 0.017 (2) | 0.002 (3) |
C7 | 0.058 (3) | 0.063 (4) | 0.043 (3) | 0.000 (3) | 0.013 (3) | −0.008 (3) |
C8 | 0.100 (5) | 0.084 (5) | 0.039 (3) | −0.007 (4) | 0.030 (3) | 0.002 (3) |
C9 | 0.147 (8) | 0.097 (6) | 0.067 (4) | −0.031 (6) | 0.061 (5) | −0.003 (4) |
C21 | 0.054 (3) | 0.041 (3) | 0.032 (2) | −0.003 (3) | 0.019 (2) | −0.004 (2) |
C22 | 0.054 (3) | 0.037 (3) | 0.049 (3) | −0.006 (2) | 0.023 (2) | 0.002 (2) |
C23 | 0.061 (3) | 0.049 (3) | 0.044 (3) | 0.003 (3) | 0.016 (2) | 0.002 (3) |
C24 | 0.051 (3) | 0.051 (3) | 0.047 (3) | −0.003 (3) | 0.017 (2) | −0.002 (3) |
C25 | 0.061 (4) | 0.045 (3) | 0.054 (3) | −0.010 (3) | 0.026 (3) | 0.001 (3) |
C26 | 0.056 (3) | 0.039 (3) | 0.046 (3) | 0.000 (3) | 0.019 (2) | 0.003 (2) |
C51 | 0.040 (3) | 0.062 (4) | 0.047 (3) | −0.001 (3) | 0.006 (2) | 0.008 (3) |
C52 | 0.052 (3) | 0.076 (4) | 0.061 (4) | 0.007 (3) | 0.020 (3) | 0.003 (3) |
C53 | 0.062 (4) | 0.093 (6) | 0.081 (5) | 0.013 (4) | 0.018 (3) | −0.002 (4) |
C54 | 0.063 (4) | 0.100 (6) | 0.085 (5) | 0.016 (4) | 0.013 (4) | 0.028 (5) |
C55 | 0.091 (5) | 0.151 (9) | 0.064 (4) | 0.031 (6) | 0.025 (4) | 0.048 (5) |
C56 | 0.073 (4) | 0.121 (7) | 0.055 (4) | 0.033 (5) | 0.027 (3) | 0.021 (4) |
C61 | 0.041 (3) | 0.060 (4) | 0.041 (3) | −0.003 (3) | 0.015 (2) | 0.003 (3) |
C62 | 0.061 (3) | 0.049 (3) | 0.052 (3) | 0.002 (3) | 0.022 (3) | 0.002 (3) |
C63 | 0.075 (4) | 0.063 (4) | 0.063 (4) | 0.006 (3) | 0.031 (3) | −0.008 (3) |
C64 | 0.067 (4) | 0.088 (5) | 0.039 (3) | −0.001 (4) | 0.021 (3) | −0.006 (3) |
C65 | 0.074 (4) | 0.092 (5) | 0.043 (3) | 0.019 (4) | 0.011 (3) | 0.008 (3) |
C66 | 0.056 (3) | 0.083 (5) | 0.049 (3) | 0.020 (3) | 0.014 (3) | 0.003 (3) |
F1 | 0.0389 (17) | 0.081 (3) | 0.098 (3) | 0.0006 (17) | 0.0183 (16) | 0.008 (2) |
F2 | 0.108 (3) | 0.138 (4) | 0.0422 (19) | 0.017 (3) | 0.0293 (19) | −0.012 (2) |
N1 | 0.042 (2) | 0.069 (3) | 0.039 (2) | 0.000 (2) | 0.0158 (19) | −0.008 (2) |
O1 | 0.091 (4) | 0.070 (3) | 0.097 (4) | −0.008 (3) | 0.026 (3) | −0.007 (3) |
O2 | 0.095 (3) | 0.086 (4) | 0.052 (2) | −0.013 (3) | 0.025 (2) | −0.021 (2) |
O3 | 0.075 (3) | 0.068 (3) | 0.0376 (19) | −0.009 (2) | 0.0207 (18) | −0.0008 (19) |
S1 | 0.0503 (8) | 0.0671 (11) | 0.0578 (9) | −0.0094 (8) | 0.0181 (6) | 0.0134 (8) |
Geometric parameters (Å, º) top
C2—N1 | 1.471 (6) | C24—C25 | 1.366 (8) |
C2—C21 | 1.506 (7) | C25—C26 | 1.379 (8) |
C2—C3 | 1.524 (7) | C25—H25 | 0.9300 |
C2—H2 | 0.9800 | C26—H26 | 0.9300 |
C3—C4 | 1.355 (7) | C51—C56 | 1.373 (8) |
C3—C7 | 1.459 (7) | C51—C52 | 1.397 (8) |
C4—O1 | 1.371 (7) | C51—S1 | 1.773 (6) |
C4—C5 | 1.517 (7) | C52—C53 | 1.374 (9) |
C5—C6 | 1.528 (8) | C52—H52 | 0.9300 |
C5—S1 | 1.835 (5) | C53—C54 | 1.364 (9) |
C5—H5 | 0.9800 | C53—H53 | 0.9300 |
C6—N1 | 1.471 (6) | C54—C55 | 1.384 (10) |
C6—C61 | 1.521 (7) | C54—H54 | 0.9300 |
C6—H6 | 0.9800 | C55—C56 | 1.372 (10) |
C7—O2 | 1.220 (7) | C55—H56 | 0.9300 |
C7—O3 | 1.331 (7) | C56—H36 | 0.9300 |
C8—O3 | 1.445 (6) | C61—C62 | 1.376 (8) |
C8—C9 | 1.516 (10) | C61—C66 | 1.377 (8) |
C8—H8A | 0.9700 | C62—C63 | 1.375 (8) |
C8—H8B | 0.9700 | C62—H62 | 0.9300 |
C9—H9A | 0.9600 | C63—C64 | 1.343 (9) |
C9—H9B | 0.9600 | C63—H63 | 0.9300 |
C9—H9C | 0.9600 | C64—F2 | 1.366 (6) |
C21—C22 | 1.391 (7) | C64—C65 | 1.376 (9) |
C21—C26 | 1.396 (7) | C65—C66 | 1.388 (8) |
C22—C23 | 1.374 (7) | C65—H65 | 0.9300 |
C22—H22 | 0.9300 | C66—H66 | 0.9300 |
C23—C24 | 1.372 (8) | N1—H1 | 0.85 (6) |
C23—H23 | 0.9300 | O1—H1A | 0.8200 |
C24—F1 | 1.356 (6) | | |
| | | |
N1—C2—C21 | 106.1 (4) | C25—C24—C23 | 122.0 (5) |
N1—C2—C3 | 109.1 (4) | C24—C25—C26 | 118.8 (5) |
C21—C2—C3 | 112.3 (4) | C24—C25—H25 | 120.6 |
N1—C2—H2 | 109.7 | C26—C25—H25 | 120.6 |
C21—C2—H2 | 109.7 | C25—C26—C21 | 121.4 (5) |
C3—C2—H2 | 109.7 | C25—C26—H26 | 119.3 |
C4—C3—C7 | 120.2 (5) | C21—C26—H26 | 119.3 |
C4—C3—C2 | 122.9 (4) | C56—C51—C52 | 117.9 (6) |
C7—C3—C2 | 117.0 (5) | C56—C51—S1 | 124.2 (5) |
C3—C4—O1 | 123.3 (5) | C52—C51—S1 | 117.7 (4) |
C3—C4—C5 | 121.4 (5) | C53—C52—C51 | 121.5 (6) |
O1—C4—C5 | 115.3 (5) | C53—C52—H52 | 119.3 |
C4—C5—C6 | 111.3 (4) | C51—C52—H52 | 119.3 |
C4—C5—S1 | 113.3 (4) | C54—C53—C52 | 119.5 (6) |
C6—C5—S1 | 111.9 (4) | C54—C53—H53 | 120.2 |
C4—C5—H5 | 106.6 | C52—C53—H53 | 120.2 |
C6—C5—H5 | 106.6 | C53—C54—C55 | 119.8 (7) |
S1—C5—H5 | 106.6 | C53—C54—H54 | 120.1 |
N1—C6—C61 | 107.7 (4) | C55—C54—H54 | 120.1 |
N1—C6—C5 | 105.8 (4) | C56—C55—C54 | 120.5 (6) |
C61—C6—C5 | 113.3 (4) | C56—C55—H56 | 119.7 |
N1—C6—H6 | 110.0 | C54—C55—H56 | 119.7 |
C61—C6—H6 | 110.0 | C55—C56—C51 | 120.7 (6) |
C5—C6—H6 | 110.0 | C55—C56—H36 | 119.6 |
O2—C7—O3 | 121.8 (5) | C51—C56—H36 | 119.6 |
O2—C7—C3 | 125.4 (6) | C62—C61—C66 | 118.4 (5) |
O3—C7—C3 | 112.9 (5) | C62—C61—C6 | 121.4 (5) |
O3—C8—C9 | 105.6 (5) | C66—C61—C6 | 120.1 (5) |
O3—C8—H8A | 110.6 | C63—C62—C61 | 121.2 (6) |
C9—C8—H8A | 110.6 | C63—C62—H62 | 119.4 |
O3—C8—H8B | 110.6 | C61—C62—H62 | 119.4 |
C9—C8—H8B | 110.6 | C64—C63—C62 | 119.0 (6) |
H8A—C8—H8B | 108.8 | C64—C63—H63 | 120.5 |
C8—C9—H9A | 109.5 | C62—C63—H63 | 120.5 |
C8—C9—H9B | 109.5 | C63—C64—F2 | 119.9 (6) |
H9A—C9—H9B | 109.5 | C63—C64—C65 | 122.8 (5) |
C8—C9—H9C | 109.5 | F2—C64—C65 | 117.4 (6) |
H9A—C9—H9C | 109.5 | C64—C65—C66 | 117.4 (6) |
H9B—C9—H9C | 109.5 | C64—C65—H65 | 121.3 |
C22—C21—C26 | 117.3 (5) | C66—C65—H65 | 121.3 |
C22—C21—C2 | 120.6 (4) | C61—C66—C65 | 121.3 (6) |
C26—C21—C2 | 122.0 (5) | C61—C66—H66 | 119.3 |
C23—C22—C21 | 121.8 (5) | C65—C66—H66 | 119.3 |
C23—C22—H22 | 119.1 | C6—N1—C2 | 114.9 (4) |
C21—C22—H22 | 119.1 | C6—N1—H1 | 107 (4) |
C24—C23—C22 | 118.6 (5) | C2—N1—H1 | 118 (4) |
C24—C23—H23 | 120.7 | C4—O1—H1A | 109.5 |
C22—C23—H23 | 120.7 | C7—O3—C8 | 116.4 (5) |
F1—C24—C25 | 119.2 (5) | C51—S1—C5 | 105.1 (3) |
F1—C24—C23 | 118.8 (5) | | |
| | | |
N1—C2—C3—C4 | −6.5 (7) | C56—C51—C52—C53 | −1.0 (10) |
C21—C2—C3—C4 | −123.9 (5) | S1—C51—C52—C53 | 175.1 (5) |
N1—C2—C3—C7 | 175.1 (5) | C51—C52—C53—C54 | 1.3 (11) |
C21—C2—C3—C7 | 57.8 (6) | C52—C53—C54—C55 | 0.1 (12) |
C7—C3—C4—O1 | −10.9 (9) | C53—C54—C55—C56 | −1.7 (14) |
C2—C3—C4—O1 | 170.8 (5) | C54—C55—C56—C51 | 2.0 (13) |
C7—C3—C4—C5 | 171.0 (5) | C52—C51—C56—C55 | −0.7 (11) |
C2—C3—C4—C5 | −7.2 (8) | S1—C51—C56—C55 | −176.4 (6) |
C3—C4—C5—C6 | −15.9 (7) | N1—C6—C61—C62 | −118.6 (6) |
O1—C4—C5—C6 | 165.8 (5) | C5—C6—C61—C62 | 124.8 (6) |
C3—C4—C5—S1 | −143.1 (5) | N1—C6—C61—C66 | 59.0 (7) |
O1—C4—C5—S1 | 38.6 (6) | C5—C6—C61—C66 | −57.6 (7) |
C4—C5—C6—N1 | 50.3 (6) | C66—C61—C62—C63 | −0.9 (9) |
S1—C5—C6—N1 | 178.3 (3) | C6—C61—C62—C63 | 176.7 (5) |
C4—C5—C6—C61 | 168.1 (4) | C61—C62—C63—C64 | 0.1 (9) |
S1—C5—C6—C61 | −64.0 (5) | C62—C63—C64—F2 | 179.3 (6) |
C4—C3—C7—O2 | 15.2 (9) | C62—C63—C64—C65 | 0.7 (10) |
C2—C3—C7—O2 | −166.5 (6) | C63—C64—C65—C66 | −0.7 (10) |
C4—C3—C7—O3 | −164.7 (5) | F2—C64—C65—C66 | −179.3 (6) |
C2—C3—C7—O3 | 13.7 (7) | C62—C61—C66—C65 | 0.9 (9) |
N1—C2—C21—C22 | −57.4 (6) | C6—C61—C66—C65 | −176.8 (6) |
C3—C2—C21—C22 | 61.7 (6) | C64—C65—C66—C61 | −0.1 (10) |
N1—C2—C21—C26 | 119.7 (5) | C61—C6—N1—C2 | 169.0 (5) |
C3—C2—C21—C26 | −121.2 (5) | C5—C6—N1—C2 | −69.5 (6) |
C26—C21—C22—C23 | −0.6 (7) | C21—C2—N1—C6 | 167.6 (5) |
C2—C21—C22—C23 | 176.6 (5) | C3—C2—N1—C6 | 46.4 (6) |
C21—C22—C23—C24 | 0.3 (8) | O2—C7—O3—C8 | 1.4 (9) |
C22—C23—C24—F1 | 179.9 (5) | C3—C7—O3—C8 | −178.8 (5) |
C22—C23—C24—C25 | 0.5 (8) | C9—C8—O3—C7 | 174.3 (6) |
F1—C24—C25—C26 | 179.6 (5) | C56—C51—S1—C5 | −60.7 (6) |
C23—C24—C25—C26 | −1.0 (8) | C52—C51—S1—C5 | 123.6 (5) |
C24—C25—C26—C21 | 0.6 (8) | C4—C5—S1—C51 | 71.2 (5) |
C22—C21—C26—C25 | 0.1 (7) | C6—C5—S1—C51 | −55.7 (4) |
C2—C21—C26—C25 | −177.1 (5) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···F1i | 0.85 (6) | 2.46 (7) | 3.305 (7) | 179 |
C65—H65···O2ii | 0.93 | 2.37 | 3.252 (8) | 158 |
O1—H1A···S1 | 0.82 | 2.47 | 3.019 (5) | 125 |
C23—H23···Cg1iii | 0.93 | 2.89 | 3.504 (5) | 125 |
C53—H53···Cg2iv | 0.93 | 2.93 | 3.736 (8) | 146 |
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) x, −y+5/2, z−1/2; (iii) −x, y+1/2, −z+1/2; (iv) −x+1, y−1/2, −z+1/2. |