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There are two independent molecules in the asymmetric unit of the title compound, C
14H
16N
2O
2S. The quinoline system of each molecule is planar [maximum deviation from planarity = 0.05 (2) Å], while the piperidine ring exibits a chair conformation. Intermolecular C—H
O hydrogen bonds connect symmetry-related molecules.
Supporting information
CCDC reference: 643045
Key indicators
- Single-crystal X-ray study
- T = 299 K
- Mean (C-C) = 0.004 Å
- R factor = 0.045
- wR factor = 0.131
- Data-to-parameter ratio = 10.5
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H11D .. O2B .. 2.68 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 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: CAD-4-PC Software (Nonius, 1996); cell refinement: CAD-4-PC Software; data reduction: REDU4 (Stoe & Cie, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
8-(Piperidin-1-ylsulfonyl)quinoline
top
Crystal data top
C14H16N2O2S | Z = 4 |
Mr = 276.35 | F(000) = 584 |
Triclinic, P1 | Dx = 1.398 Mg m−3 |
Hall symbol: -P 1 | Cu Kα radiation, λ = 1.54180 Å |
a = 7.2682 (7) Å | Cell parameters from 25 reflections |
b = 14.319 (2) Å | θ = 5.8–26.8° |
c = 14.411 (2) Å | µ = 2.19 mm−1 |
α = 111.31 (2)° | T = 299 K |
β = 101.49 (1)° | Prism, colourless |
γ = 100.71 (1)° | 0.60 × 0.60 × 0.50 mm |
V = 1313.3 (3) Å3 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.063 |
Radiation source: fine-focus sealed tube | θmax = 66.9°, θmin = 3.4° |
Graphite monochromator | h = −8→1 |
ω/2θ scans | k = −15→17 |
5753 measured reflections | l = −17→17 |
4633 independent reflections | 3 standard reflections every 120 min |
4440 reflections with I > 2σ(I) | intensity decay: 1.0% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | Only H-atom coordinates refined |
wR(F2) = 0.131 | w = 1/[σ2(Fo2) + (0.0824P)2 + 0.6511P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
4633 reflections | Δρmax = 0.51 e Å−3 |
440 parameters | Δρmin = −0.38 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0304 (15) |
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 | |
C1A | 0.4903 (3) | 0.28065 (14) | −0.01137 (14) | 0.0301 (4) | |
C2A | 0.6855 (3) | 0.28703 (16) | 0.01783 (16) | 0.0377 (4) | |
H2A | 0.731 (3) | 0.254 (2) | 0.061 (2) | 0.045* | |
C3A | 0.8217 (3) | 0.34753 (17) | −0.00978 (17) | 0.0413 (5) | |
H3A | 0.952 (4) | 0.346 (2) | 0.009 (2) | 0.050* | |
C4A | 0.7614 (3) | 0.40182 (17) | −0.06376 (17) | 0.0392 (5) | |
H4A | 0.851 (4) | 0.445 (2) | −0.0829 (19) | 0.047* | |
C5A | 0.5614 (3) | 0.39600 (14) | −0.09728 (14) | 0.0315 (4) | |
C6A | 0.4920 (3) | 0.44812 (18) | −0.15720 (17) | 0.0410 (5) | |
H6A | 0.579 (4) | 0.489 (2) | −0.170 (2) | 0.049* | |
C7A | 0.2978 (3) | 0.43385 (19) | −0.19194 (18) | 0.0433 (5) | |
H7A | 0.243 (4) | 0.466 (2) | −0.234 (2) | 0.052* | |
C8A | 0.1704 (3) | 0.36765 (17) | −0.16603 (16) | 0.0375 (4) | |
H8A | 0.028 (4) | 0.356 (2) | −0.1922 (19) | 0.045* | |
C9A | 0.4215 (2) | 0.33293 (13) | −0.07273 (13) | 0.0276 (4) | |
C10A | 0.0036 (3) | 0.10050 (17) | −0.13286 (19) | 0.0421 (5) | |
H3 | −0.047 (4) | 0.154 (2) | −0.092 (2) | 0.050* | |
H11 | 0.030 (4) | 0.117 (2) | −0.192 (2) | 0.050* | |
C11A | −0.1430 (3) | −0.00499 (18) | −0.1688 (2) | 0.0473 (5) | |
H11A | −0.260 (4) | −0.008 (2) | −0.214 (2) | 0.057* | |
H11B | −0.164 (4) | −0.012 (2) | −0.109 (2) | 0.057* | |
C12A | −0.0624 (4) | −0.09299 (19) | −0.2241 (2) | 0.0535 (6) | |
H12A | −0.165 (4) | −0.162 (3) | −0.249 (2) | 0.064* | |
H12B | −0.042 (4) | −0.088 (2) | −0.285 (3) | 0.064* | |
C13A | 0.1323 (4) | −0.08575 (18) | −0.1558 (2) | 0.0486 (6) | |
H13A | 0.191 (4) | −0.136 (2) | −0.189 (2) | 0.058* | |
H13B | 0.121 (4) | −0.091 (2) | −0.092 (2) | 0.058* | |
C14A | 0.2767 (3) | 0.02080 (18) | −0.1189 (2) | 0.0450 (5) | |
H14A | 0.406 (4) | 0.030 (2) | −0.072 (2) | 0.054* | |
H14B | 0.301 (4) | 0.026 (2) | −0.182 (2) | 0.054* | |
N1A | 0.1881 (2) | 0.10247 (13) | −0.06614 (13) | 0.0371 (4) | |
N2A | 0.2261 (2) | 0.31981 (13) | −0.10744 (13) | 0.0332 (4) | |
O1A | 0.4522 (2) | 0.17519 (14) | 0.09727 (12) | 0.0514 (4) | |
O2A | 0.2070 (2) | 0.26934 (12) | 0.07491 (12) | 0.0460 (4) | |
S1A | 0.32791 (7) | 0.20723 (4) | 0.03159 (3) | 0.03388 (18) | |
C1B | 0.2880 (3) | 0.67671 (16) | 0.53983 (16) | 0.0361 (4) | |
C2B | 0.3608 (3) | 0.68812 (19) | 0.63990 (17) | 0.0445 (5) | |
H2B | 0.399 (4) | 0.757 (2) | 0.695 (2) | 0.053* | |
C3B | 0.3720 (4) | 0.6008 (2) | 0.66135 (19) | 0.0506 (6) | |
H3B | 0.428 (4) | 0.611 (2) | 0.732 (2) | 0.061* | |
C4B | 0.3055 (4) | 0.50297 (19) | 0.58280 (18) | 0.0480 (5) | |
H4B | 0.311 (4) | 0.443 (2) | 0.599 (2) | 0.058* | |
C5B | 0.2328 (3) | 0.48814 (16) | 0.47867 (16) | 0.0366 (4) | |
C6B | 0.1665 (4) | 0.38803 (18) | 0.39430 (19) | 0.0461 (5) | |
H6B | 0.170 (4) | 0.330 (2) | 0.409 (2) | 0.055* | |
C7B | 0.1069 (4) | 0.37993 (18) | 0.29566 (19) | 0.0471 (5) | |
H7B | 0.060 (4) | 0.316 (2) | 0.238 (2) | 0.056* | |
C8B | 0.1127 (3) | 0.47165 (18) | 0.28054 (17) | 0.0435 (5) | |
H8B | 0.067 (4) | 0.465 (2) | 0.208 (2) | 0.052* | |
C9B | 0.2275 (3) | 0.57593 (15) | 0.45501 (15) | 0.0328 (4) | |
C10B | 0.6184 (3) | 0.8354 (2) | 0.5074 (2) | 0.0494 (6) | |
H10C | 0.640 (4) | 0.858 (2) | 0.582 (2) | 0.059* | |
H10D | 0.652 (4) | 0.766 (2) | 0.482 (2) | 0.059* | |
C11B | 0.7441 (4) | 0.9127 (2) | 0.4802 (2) | 0.0514 (6) | |
H11C | 0.721 (4) | 0.977 (3) | 0.510 (2) | 0.062* | |
H11D | 0.884 (4) | 0.918 (2) | 0.509 (2) | 0.062* | |
C12B | 0.6913 (4) | 0.8791 (2) | 0.3638 (2) | 0.0593 (7) | |
H12C | 0.725 (4) | 0.813 (3) | 0.335 (2) | 0.071* | |
H12D | 0.774 (5) | 0.928 (3) | 0.347 (2) | 0.071* | |
C13B | 0.4763 (4) | 0.8616 (2) | 0.31902 (19) | 0.0548 (6) | |
H13C | 0.435 (4) | 0.834 (3) | 0.247 (3) | 0.066* | |
H13D | 0.451 (4) | 0.929 (3) | 0.348 (2) | 0.066* | |
C14B | 0.3507 (4) | 0.7841 (2) | 0.34707 (17) | 0.0518 (6) | |
H14C | 0.208 (4) | 0.778 (2) | 0.327 (2) | 0.062* | |
H14D | 0.372 (4) | 0.714 (3) | 0.313 (2) | 0.062* | |
N1B | 0.4105 (3) | 0.82026 (14) | 0.46086 (13) | 0.0383 (4) | |
N2B | 0.1688 (3) | 0.56687 (14) | 0.35571 (13) | 0.0390 (4) | |
O1B | 0.3226 (3) | 0.87270 (14) | 0.62425 (15) | 0.0693 (6) | |
O2B | 0.0662 (3) | 0.76824 (15) | 0.45763 (18) | 0.0670 (5) | |
S1B | 0.25998 (8) | 0.79071 (4) | 0.52125 (4) | 0.04275 (19) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1A | 0.0319 (9) | 0.0246 (9) | 0.0286 (9) | 0.0067 (7) | 0.0062 (7) | 0.0077 (7) |
C2A | 0.0362 (10) | 0.0335 (10) | 0.0383 (10) | 0.0126 (8) | 0.0031 (8) | 0.0121 (8) |
C3A | 0.0266 (9) | 0.0402 (11) | 0.0490 (12) | 0.0107 (8) | 0.0077 (8) | 0.0107 (9) |
C4A | 0.0314 (10) | 0.0355 (11) | 0.0478 (12) | 0.0062 (8) | 0.0161 (8) | 0.0133 (9) |
C5A | 0.0326 (9) | 0.0277 (9) | 0.0341 (9) | 0.0091 (7) | 0.0137 (7) | 0.0104 (7) |
C6A | 0.0458 (11) | 0.0406 (12) | 0.0480 (12) | 0.0137 (9) | 0.0238 (9) | 0.0250 (10) |
C7A | 0.0500 (12) | 0.0512 (13) | 0.0450 (12) | 0.0241 (10) | 0.0190 (9) | 0.0304 (10) |
C8A | 0.0339 (10) | 0.0425 (11) | 0.0380 (10) | 0.0150 (8) | 0.0084 (8) | 0.0178 (9) |
C9A | 0.0295 (8) | 0.0234 (9) | 0.0271 (8) | 0.0080 (7) | 0.0083 (7) | 0.0071 (7) |
C10A | 0.0391 (10) | 0.0340 (11) | 0.0494 (12) | 0.0104 (9) | 0.0039 (9) | 0.0180 (9) |
C11A | 0.0393 (11) | 0.0381 (12) | 0.0547 (14) | 0.0050 (9) | 0.0030 (10) | 0.0170 (10) |
C12A | 0.0585 (14) | 0.0338 (12) | 0.0483 (13) | 0.0053 (10) | 0.0001 (11) | 0.0072 (10) |
C13A | 0.0596 (14) | 0.0296 (11) | 0.0491 (13) | 0.0166 (10) | 0.0091 (11) | 0.0100 (10) |
C14A | 0.0433 (11) | 0.0380 (12) | 0.0537 (13) | 0.0155 (9) | 0.0153 (10) | 0.0166 (10) |
N1A | 0.0354 (8) | 0.0266 (8) | 0.0437 (9) | 0.0072 (7) | 0.0052 (7) | 0.0125 (7) |
N2A | 0.0289 (8) | 0.0328 (8) | 0.0373 (8) | 0.0078 (6) | 0.0085 (6) | 0.0149 (7) |
O1A | 0.0567 (9) | 0.0552 (10) | 0.0451 (9) | 0.0115 (7) | 0.0027 (7) | 0.0323 (8) |
O2A | 0.0548 (9) | 0.0457 (9) | 0.0412 (8) | 0.0152 (7) | 0.0248 (7) | 0.0160 (7) |
S1A | 0.0390 (3) | 0.0323 (3) | 0.0310 (3) | 0.0076 (2) | 0.00858 (19) | 0.0160 (2) |
C1B | 0.0413 (10) | 0.0309 (10) | 0.0415 (11) | 0.0118 (8) | 0.0203 (8) | 0.0161 (8) |
C2B | 0.0531 (12) | 0.0421 (12) | 0.0376 (11) | 0.0102 (10) | 0.0186 (9) | 0.0146 (9) |
C3B | 0.0654 (15) | 0.0537 (14) | 0.0377 (12) | 0.0165 (11) | 0.0172 (10) | 0.0232 (10) |
C4B | 0.0647 (14) | 0.0463 (13) | 0.0486 (13) | 0.0216 (11) | 0.0238 (11) | 0.0301 (11) |
C5B | 0.0404 (10) | 0.0343 (10) | 0.0426 (11) | 0.0132 (8) | 0.0195 (8) | 0.0190 (9) |
C6B | 0.0588 (13) | 0.0312 (11) | 0.0545 (13) | 0.0162 (10) | 0.0229 (10) | 0.0197 (10) |
C7B | 0.0571 (13) | 0.0319 (11) | 0.0456 (12) | 0.0100 (9) | 0.0165 (10) | 0.0093 (9) |
C8B | 0.0474 (11) | 0.0423 (12) | 0.0369 (11) | 0.0090 (9) | 0.0105 (9) | 0.0151 (9) |
C9B | 0.0329 (9) | 0.0329 (10) | 0.0378 (10) | 0.0116 (8) | 0.0162 (8) | 0.0162 (8) |
C10B | 0.0468 (12) | 0.0545 (14) | 0.0547 (14) | 0.0141 (11) | 0.0104 (10) | 0.0338 (12) |
C11B | 0.0436 (12) | 0.0504 (14) | 0.0659 (15) | 0.0126 (10) | 0.0195 (11) | 0.0290 (12) |
C12B | 0.0785 (18) | 0.0475 (15) | 0.0690 (17) | 0.0226 (13) | 0.0448 (15) | 0.0286 (13) |
C13B | 0.0870 (19) | 0.0423 (13) | 0.0363 (12) | 0.0121 (12) | 0.0186 (12) | 0.0205 (10) |
C14B | 0.0698 (16) | 0.0403 (13) | 0.0329 (11) | 0.0017 (11) | 0.0053 (10) | 0.0134 (9) |
N1B | 0.0435 (9) | 0.0365 (9) | 0.0349 (9) | 0.0072 (7) | 0.0094 (7) | 0.0177 (7) |
N2B | 0.0462 (9) | 0.0335 (9) | 0.0389 (9) | 0.0103 (7) | 0.0121 (7) | 0.0173 (7) |
O1B | 0.1240 (17) | 0.0352 (9) | 0.0575 (11) | 0.0281 (10) | 0.0497 (11) | 0.0140 (8) |
O2B | 0.0507 (10) | 0.0592 (11) | 0.1116 (16) | 0.0310 (8) | 0.0307 (10) | 0.0467 (11) |
S1B | 0.0552 (3) | 0.0294 (3) | 0.0526 (3) | 0.0183 (2) | 0.0270 (3) | 0.0178 (2) |
Geometric parameters (Å, º) top
C1A—C2A | 1.373 (3) | C1B—C2B | 1.371 (3) |
C1A—C9A | 1.427 (3) | C1B—C9B | 1.428 (3) |
C1A—S1A | 1.785 (2) | C1B—S1B | 1.788 (2) |
C2A—C3A | 1.406 (3) | C2B—C3B | 1.405 (3) |
C2A—H2A | 0.95 (3) | C2B—H2B | 0.96 (3) |
C3A—C4A | 1.354 (3) | C3B—C4B | 1.362 (4) |
C3A—H3A | 0.94 (3) | C3B—H3B | 0.96 (3) |
C4A—C5A | 1.414 (3) | C4B—C5B | 1.410 (3) |
C4A—H4A | 0.97 (3) | C4B—H4B | 0.98 (3) |
C5A—C6A | 1.411 (3) | C5B—C6B | 1.417 (3) |
C5A—C9A | 1.417 (3) | C5B—C9B | 1.422 (3) |
C6A—C7A | 1.350 (3) | C6B—C7B | 1.356 (3) |
C6A—H6A | 0.88 (3) | C6B—H6B | 0.94 (3) |
C7A—C8A | 1.401 (3) | C7B—C8B | 1.402 (3) |
C7A—H7A | 0.95 (3) | C7B—H7B | 0.93 (3) |
C8A—N2A | 1.316 (3) | C8B—N2B | 1.320 (3) |
C8A—H8A | 0.99 (2) | C8B—H8B | 0.99 (3) |
C9A—N2A | 1.361 (2) | C9B—N2B | 1.359 (3) |
C10A—N1A | 1.475 (3) | C10B—N1B | 1.466 (3) |
C10A—C11A | 1.516 (3) | C10B—C11B | 1.515 (3) |
C10A—H3 | 0.97 (3) | C10B—H10C | 0.97 (3) |
C10A—H11 | 1.00 (3) | C10B—H10D | 1.02 (3) |
C11A—C12A | 1.516 (3) | C11B—C12B | 1.510 (4) |
C11A—H11A | 0.94 (3) | C11B—H11C | 0.92 (3) |
C11A—H11B | 0.94 (3) | C11B—H11D | 1.00 (3) |
C12A—C13A | 1.516 (3) | C12B—C13B | 1.502 (4) |
C12A—H12A | 1.01 (3) | C12B—H12C | 0.98 (3) |
C12A—H12B | 0.95 (3) | C12B—H12D | 0.97 (4) |
C13A—C14A | 1.519 (3) | C13B—C14B | 1.525 (4) |
C13A—H13A | 0.93 (3) | C13B—H13C | 0.93 (3) |
C13A—H13B | 0.96 (3) | C13B—H13D | 0.97 (3) |
C14A—N1A | 1.480 (3) | C14B—N1B | 1.470 (3) |
C14A—H14A | 0.99 (3) | C14B—H14C | 1.00 (3) |
C14A—H14B | 0.98 (3) | C14B—H14D | 1.00 (3) |
N1A—S1A | 1.6107 (17) | N1B—S1B | 1.6148 (18) |
O1A—S1A | 1.4321 (15) | O1B—S1B | 1.4333 (19) |
O2A—S1A | 1.4350 (16) | O2B—S1B | 1.425 (2) |
| | | |
C2A—C1A—C9A | 120.54 (18) | C2B—C1B—C9B | 120.45 (19) |
C2A—C1A—S1A | 117.97 (15) | C2B—C1B—S1B | 117.57 (16) |
C9A—C1A—S1A | 121.49 (14) | C9B—C1B—S1B | 121.89 (15) |
C1A—C2A—C3A | 120.54 (19) | C1B—C2B—C3B | 120.8 (2) |
C1A—C2A—H2A | 119.9 (15) | C1B—C2B—H2B | 117.8 (16) |
C3A—C2A—H2A | 119.4 (15) | C3B—C2B—H2B | 121.3 (16) |
C4A—C3A—C2A | 120.05 (18) | C4B—C3B—C2B | 120.2 (2) |
C4A—C3A—H3A | 123.3 (17) | C4B—C3B—H3B | 120.5 (18) |
C2A—C3A—H3A | 116.6 (17) | C2B—C3B—H3B | 119.3 (19) |
C3A—C4A—C5A | 121.39 (19) | C3B—C4B—C5B | 120.7 (2) |
C3A—C4A—H4A | 122.2 (15) | C3B—C4B—H4B | 119.3 (17) |
C5A—C4A—H4A | 116.4 (15) | C5B—C4B—H4B | 120.0 (17) |
C6A—C5A—C9A | 117.66 (17) | C4B—C5B—C6B | 122.6 (2) |
C6A—C5A—C4A | 123.05 (18) | C4B—C5B—C9B | 119.89 (19) |
C9A—C5A—C4A | 119.26 (18) | C6B—C5B—C9B | 117.51 (19) |
C7A—C6A—C5A | 119.8 (2) | C7B—C6B—C5B | 119.4 (2) |
C7A—C6A—H6A | 122.6 (17) | C7B—C6B—H6B | 122.4 (17) |
C5A—C6A—H6A | 117.5 (17) | C5B—C6B—H6B | 118.1 (17) |
C6A—C7A—C8A | 118.33 (19) | C6B—C7B—C8B | 118.5 (2) |
C6A—C7A—H7A | 123.1 (16) | C6B—C7B—H7B | 123.1 (18) |
C8A—C7A—H7A | 118.5 (16) | C8B—C7B—H7B | 118.4 (18) |
N2A—C8A—C7A | 124.81 (18) | N2B—C8B—C7B | 125.0 (2) |
N2A—C8A—H8A | 116.4 (15) | N2B—C8B—H8B | 116.8 (16) |
C7A—C8A—H8A | 118.7 (15) | C7B—C8B—H8B | 118.2 (16) |
N2A—C9A—C5A | 121.99 (17) | N2B—C9B—C5B | 122.47 (18) |
N2A—C9A—C1A | 119.89 (16) | N2B—C9B—C1B | 119.71 (18) |
C5A—C9A—C1A | 118.11 (16) | C5B—C9B—C1B | 117.83 (18) |
N1A—C10A—C11A | 108.56 (18) | N1B—C10B—C11B | 110.23 (19) |
N1A—C10A—H3 | 108.7 (15) | N1B—C10B—H10C | 107.4 (16) |
C11A—C10A—H3 | 108.5 (16) | C11B—C10B—H10C | 112.5 (18) |
N1A—C10A—H11 | 109.3 (14) | N1B—C10B—H10D | 110.7 (16) |
C11A—C10A—H11 | 113.3 (15) | C11B—C10B—H10D | 109.5 (17) |
H3—C10A—H11 | 108 (2) | H10C—C10B—H10D | 106 (2) |
C12A—C11A—C10A | 111.0 (2) | C12B—C11B—C10B | 110.9 (2) |
C12A—C11A—H11A | 110.0 (17) | C12B—C11B—H11C | 108.6 (19) |
C10A—C11A—H11A | 109.3 (18) | C10B—C11B—H11C | 107.8 (19) |
C12A—C11A—H11B | 108.1 (18) | C12B—C11B—H11D | 110.8 (17) |
C10A—C11A—H11B | 107.2 (18) | C10B—C11B—H11D | 108.5 (18) |
H11A—C11A—H11B | 111 (2) | H11C—C11B—H11D | 110 (3) |
C13A—C12A—C11A | 111.0 (2) | C13B—C12B—C11B | 110.9 (2) |
C13A—C12A—H12A | 114.0 (17) | C13B—C12B—H12C | 109.9 (19) |
C11A—C12A—H12A | 108.6 (17) | C11B—C12B—H12C | 106.4 (19) |
C13A—C12A—H12B | 108.1 (18) | C13B—C12B—H12D | 113.7 (19) |
C11A—C12A—H12B | 108.8 (19) | C11B—C12B—H12D | 110.7 (19) |
H12A—C12A—H12B | 106 (2) | H12C—C12B—H12D | 105 (3) |
C12A—C13A—C14A | 111.0 (2) | C12B—C13B—C14B | 112.1 (2) |
C12A—C13A—H13A | 113.5 (17) | C12B—C13B—H13C | 113.6 (18) |
C14A—C13A—H13A | 107.2 (18) | C14B—C13B—H13C | 104.6 (19) |
C12A—C13A—H13B | 112.1 (17) | C12B—C13B—H13D | 106.6 (18) |
C14A—C13A—H13B | 103.9 (18) | C14B—C13B—H13D | 109.6 (19) |
H13A—C13A—H13B | 109 (2) | H13C—C13B—H13D | 110 (3) |
N1A—C14A—C13A | 108.89 (18) | N1B—C14B—C13B | 108.68 (19) |
N1A—C14A—H14A | 110.0 (16) | N1B—C14B—H14C | 105.2 (17) |
C13A—C14A—H14A | 114.2 (16) | C13B—C14B—H14C | 114.6 (17) |
N1A—C14A—H14B | 111.2 (16) | N1B—C14B—H14D | 110.2 (17) |
C13A—C14A—H14B | 105.9 (16) | C13B—C14B—H14D | 108.5 (17) |
H14A—C14A—H14B | 107 (2) | H14C—C14B—H14D | 110 (2) |
C10A—N1A—C14A | 113.88 (17) | C10B—N1B—C14B | 114.6 (2) |
C10A—N1A—S1A | 122.34 (14) | C10B—N1B—S1B | 117.13 (15) |
C14A—N1A—S1A | 118.65 (14) | C14B—N1B—S1B | 121.57 (16) |
C8A—N2A—C9A | 117.32 (17) | C8B—N2B—C9B | 117.00 (18) |
O2A—S1A—O1A | 118.59 (10) | O2B—S1B—O1B | 118.69 (13) |
O2A—S1A—N1A | 108.20 (9) | O2B—S1B—N1B | 107.92 (11) |
O1A—S1A—N1A | 106.93 (10) | O1B—S1B—N1B | 106.91 (11) |
O2A—S1A—C1A | 108.34 (9) | O2B—S1B—C1B | 108.83 (11) |
O1A—S1A—C1A | 104.84 (9) | O1B—S1B—C1B | 104.71 (11) |
N1A—S1A—C1A | 109.74 (9) | N1B—S1B—C1B | 109.54 (9) |
| | | |
C9A—C1A—C2A—C3A | 1.8 (3) | C9B—C1B—C2B—C3B | −1.9 (3) |
S1A—C1A—C2A—C3A | −177.19 (15) | S1B—C1B—C2B—C3B | 174.80 (18) |
C1A—C2A—C3A—C4A | 1.3 (3) | C1B—C2B—C3B—C4B | −1.8 (4) |
C2A—C3A—C4A—C5A | −2.6 (3) | C2B—C3B—C4B—C5B | 2.9 (4) |
C3A—C4A—C5A—C6A | −177.4 (2) | C3B—C4B—C5B—C6B | 178.5 (2) |
C3A—C4A—C5A—C9A | 0.8 (3) | C3B—C4B—C5B—C9B | −0.4 (3) |
C9A—C5A—C6A—C7A | −2.3 (3) | C4B—C5B—C6B—C7B | −177.0 (2) |
C4A—C5A—C6A—C7A | 175.9 (2) | C9B—C5B—C6B—C7B | 1.9 (3) |
C5A—C6A—C7A—C8A | 0.6 (3) | C5B—C6B—C7B—C8B | −0.1 (3) |
C6A—C7A—C8A—N2A | 1.9 (3) | C6B—C7B—C8B—N2B | −1.4 (4) |
C6A—C5A—C9A—N2A | 1.8 (3) | C4B—C5B—C9B—N2B | 176.44 (19) |
C4A—C5A—C9A—N2A | −176.48 (17) | C6B—C5B—C9B—N2B | −2.4 (3) |
C6A—C5A—C9A—C1A | −179.44 (17) | C4B—C5B—C9B—C1B | −3.1 (3) |
C4A—C5A—C9A—C1A | 2.3 (3) | C6B—C5B—C9B—C1B | 177.96 (18) |
C2A—C1A—C9A—N2A | 175.25 (17) | C2B—C1B—C9B—N2B | −175.32 (19) |
S1A—C1A—C9A—N2A | −5.8 (2) | S1B—C1B—C9B—N2B | 8.1 (3) |
C2A—C1A—C9A—C5A | −3.5 (3) | C2B—C1B—C9B—C5B | 4.3 (3) |
S1A—C1A—C9A—C5A | 175.39 (13) | S1B—C1B—C9B—C5B | −172.28 (14) |
N1A—C10A—C11A—C12A | −56.3 (3) | N1B—C10B—C11B—C12B | −54.5 (3) |
C10A—C11A—C12A—C13A | 55.4 (3) | C10B—C11B—C12B—C13B | 54.3 (3) |
C11A—C12A—C13A—C14A | −54.8 (3) | C11B—C12B—C13B—C14B | −54.9 (3) |
C12A—C13A—C14A—N1A | 55.2 (3) | C12B—C13B—C14B—N1B | 54.5 (3) |
C11A—C10A—N1A—C14A | 59.8 (3) | C11B—C10B—N1B—C14B | 57.5 (3) |
C11A—C10A—N1A—S1A | −145.94 (17) | C11B—C10B—N1B—S1B | −150.63 (18) |
C13A—C14A—N1A—C10A | −59.4 (3) | C13B—C14B—N1B—C10B | −56.6 (3) |
C13A—C14A—N1A—S1A | 145.35 (17) | C13B—C14B—N1B—S1B | 152.90 (19) |
C7A—C8A—N2A—C9A | −2.4 (3) | C7B—C8B—N2B—C9B | 0.9 (3) |
C5A—C9A—N2A—C8A | 0.5 (3) | C5B—C9B—N2B—C8B | 1.1 (3) |
C1A—C9A—N2A—C8A | −178.23 (17) | C1B—C9B—N2B—C8B | −179.33 (18) |
C10A—N1A—S1A—O2A | 32.1 (2) | C10B—N1B—S1B—O2B | −173.62 (17) |
C14A—N1A—S1A—O2A | −174.81 (16) | C14B—N1B—S1B—O2B | −23.8 (2) |
C10A—N1A—S1A—O1A | 160.89 (17) | C10B—N1B—S1B—O1B | 57.6 (2) |
C14A—N1A—S1A—O1A | −46.00 (19) | C14B—N1B—S1B—O1B | −152.53 (19) |
C10A—N1A—S1A—C1A | −85.93 (19) | C10B—N1B—S1B—C1B | −55.28 (19) |
C14A—N1A—S1A—C1A | 67.17 (18) | C14B—N1B—S1B—C1B | 94.5 (2) |
C2A—C1A—S1A—O2A | 131.38 (15) | C2B—C1B—S1B—O2B | −128.92 (18) |
C9A—C1A—S1A—O2A | −47.57 (17) | C9B—C1B—S1B—O2B | 47.74 (19) |
C2A—C1A—S1A—O1A | 3.84 (18) | C2B—C1B—S1B—O1B | −1.0 (2) |
C9A—C1A—S1A—O1A | −175.12 (15) | C9B—C1B—S1B—O1B | 175.62 (17) |
C2A—C1A—S1A—N1A | −110.68 (16) | C2B—C1B—S1B—N1B | 113.31 (17) |
C9A—C1A—S1A—N1A | 70.36 (16) | C9B—C1B—S1B—N1B | −70.03 (18) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3A—H3A···O2Ai | 0.94 (3) | 2.52 (3) | 3.374 (3) | 151 (2) |
C11B—H11D···O2Bi | 1.00 (3) | 2.68 (3) | 3.388 (3) | 128 (2) |
Symmetry code: (i) x+1, y, z. |
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