Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100009148/qa0340sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100009148/qa0340Isup2.hkl |
CCDC reference: 150393
Compound (I) was prepared by the reaction of benzyl[(3aR*,4R*,7aR*)-6,6,7a-trimethylperhydroinden-4-yl]amine, (II), with tosyl chloride and triethylamine. A solution of (II) (271 mg, 1.0 mmol) and p-toluenesulfonic chloride (286 mg, 1.5 mmol) in anhydrous dichloromethane (10 ml) was treated dropwise with triethylamine (162 mg, 1.6 mmol) and stirred at ambient temperature for 16 h. An NaOH solution (5%, 20 ml) were added and the mixture stirred for a further 30 min to remove excess tosyl chloride. After separation of the phases, the aqueous phase was extracted with dichloromethane (30 ml). The combined organic phases were washed with water (20 ml), dried over MgSO4 and evaporated. Compound (I) were isolated (400 mg, 0.94 mmol, 94%) as a thick oil that crystallized after a few days. Colourless crystals suitable for X-ray diffraction were obtained in 94% yield after crystallization from n-hexane. Spectroscopic data for (I): analysis calculated for C26H35NO2S (425.62): C 73.4, H 8.3, N 3.3%; found: C 73.3, H: 8.3, N 3.2%; MS (EI, 70 eV): m/z (%): 425 (M+, 5), 351 (1), 328 (37), 270 (6), 212 (7), 174 (6), 155 (18), 106 (15), 91 (100), 65 (12); IR (KBr): ~v (cm−1): 3024 (m), 2947 (s), 2895 (s), 1456 (s), 1323 (s), 1159 (s), 1091 (s); 1H NMR (400 MHz, CDCl3): δ (p.p.m.) 0.68 (s, 3H), 0.72 (s, 3H), 0.86 (s, 3H), 0.91 (m, 1H), 0.92 (d, 2J = 14.3 Hz, 1H), 1.09 (m, 3H), 1.36 (m, 4H), 1.54 (m, 1H), 1.64 (m, 1H), 2.35 (s, 3H), 3.55 (t*, 3J = 11.2 Hz, 1H), 4.05 (d, 2J = 15.5 Hz, 1H), 4.47 (d, 2J = 15.5 Hz, 1H), 7.20 (d, 3J = 8.2 Hz, 2H), 7.24 (m, 5H), 7.61 (d, 3J = 8.2 Hz, 2H); 13C NMR (100 MHz, CDCl3): δ (p.p.m.) 21.1 (CH2), 21.5 (CH3), 27.3 (CH2), 27.8 (CH3), 31.8 (Cq), 32.1 (CH3), 34.7 (CH3), 37.0 (CH2), 41.6 (CH2), 43.7 (Cq), 47.5 (CH2), 47.5 (CH2), 49.8 (CH), 56.6 (CH), 127.1 (CH), 127.2 (CH), 128.2 (CH), 128.2 (CH), 129.5 (CH), 138.2 (Cq), 138.5 (Cq), 141.9 (Cq); m.p.: 373–374 K.
All H atoms were located in a difference electron-density map and refined isotropically; C—H 0.85 (3)–1.14 (2) Å.
Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.
C26H35NO2S | Z = 2 |
Mr = 425.61 | F(000) = 460 |
Triclinic, P1 | Dx = 1.179 Mg m−3 |
a = 9.3965 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.5437 (3) Å | Cell parameters from 13129 reflections |
c = 13.2813 (4) Å | θ = 3.2–27.4° |
α = 109.6116 (16)° | µ = 0.16 mm−1 |
β = 90.009 (2)° | T = 291 K |
γ = 103.902 (2)° | Needle, colourless |
V = 1198.48 (6) Å3 | 0.30 × 0.10 × 0.10 mm |
Nonius KappaCCD diffractometer | 3347 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.028 |
Graphite monochromator | θmax = 27.4°, θmin = 3.2° |
Detector resolution: 10 vertical, 18 horizontal pixels mm-1 | h = −12→12 |
358 frames via ω–rotation (Δω = 1°) and two times 60 s per frame with four sets at different κ angles scans | k = −13→13 |
13129 measured reflections | l = −17→17 |
5198 independent 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)] = 0.044 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.123 | All H-atom parameters refined |
S = 1.00 | Calculated w = 1/[σ2(Fo2) + (0.0746P)2] where P = (Fo2 + 2Fc2)/3 |
5198 reflections | (Δ/σ)max = 0.001 |
411 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
C26H35NO2S | γ = 103.902 (2)° |
Mr = 425.61 | V = 1198.48 (6) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.3965 (2) Å | Mo Kα radiation |
b = 10.5437 (3) Å | µ = 0.16 mm−1 |
c = 13.2813 (4) Å | T = 291 K |
α = 109.6116 (16)° | 0.30 × 0.10 × 0.10 mm |
β = 90.009 (2)° |
Nonius KappaCCD diffractometer | 3347 reflections with I > 2σ(I) |
13129 measured reflections | Rint = 0.028 |
5198 independent reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.123 | All H-atom parameters refined |
S = 1.00 | Δρmax = 0.23 e Å−3 |
5198 reflections | Δρmin = −0.23 e Å−3 |
411 parameters |
Experimental. The data collection covered almost the whole sphere of reciprocal space. The crystal-to-detector distance was 3.4 cm. Crystal decay was monitored by repeating the initial frames at the end of data collection. Analysing the duplicate reflections there was no indication for any decay. |
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 | ||
S1 | 0.97632 (4) | 0.72220 (4) | 0.16808 (3) | 0.04853 (16) | |
O1 | 1.06036 (12) | 0.63284 (13) | 0.10469 (9) | 0.0618 (3) | |
O2 | 1.04502 (12) | 0.83254 (12) | 0.26418 (9) | 0.0612 (3) | |
N1 | 0.83376 (13) | 0.62486 (12) | 0.19873 (10) | 0.0459 (3) | |
C1 | 0.4754 (3) | 0.8308 (2) | 0.28181 (19) | 0.0748 (6) | |
H1A | 0.567 (3) | 0.910 (2) | 0.3082 (17) | 0.093 (7)* | |
H1B | 0.392 (3) | 0.870 (2) | 0.3094 (17) | 0.095 (7)* | |
C2 | 0.4740 (3) | 0.7697 (3) | 0.1619 (2) | 0.0854 (7) | |
H2A | 0.370 (3) | 0.744 (3) | 0.131 (2) | 0.129 (9)* | |
H2B | 0.542 (4) | 0.829 (3) | 0.129 (3) | 0.160 (12)* | |
C3 | 0.5231 (2) | 0.6350 (3) | 0.13749 (16) | 0.0699 (5) | |
H3A | 0.603 (2) | 0.634 (2) | 0.0908 (16) | 0.084 (6)* | |
H3B | 0.430 (3) | 0.537 (2) | 0.1003 (18) | 0.102 (7)* | |
C3A | 0.57458 (17) | 0.63101 (18) | 0.24445 (13) | 0.0505 (4) | |
H3AA | 0.5517 (16) | 0.5341 (18) | 0.2433 (12) | 0.049 (4)* | |
C4 | 0.73978 (16) | 0.69718 (17) | 0.27638 (12) | 0.0421 (3) | |
H4 | 0.7585 (15) | 0.7880 (16) | 0.2698 (11) | 0.039 (4)* | |
C5 | 0.7813 (2) | 0.7121 (2) | 0.39118 (13) | 0.0541 (4) | |
H5A | 0.7545 (19) | 0.622 (2) | 0.3961 (13) | 0.061 (5)* | |
H5B | 0.8909 (19) | 0.7469 (17) | 0.4152 (12) | 0.053 (4)* | |
C6 | 0.70714 (18) | 0.8120 (2) | 0.47333 (13) | 0.0605 (5) | |
C7 | 0.5401 (2) | 0.7586 (2) | 0.44260 (15) | 0.0672 (5) | |
H7A | 0.489 (2) | 0.836 (2) | 0.4892 (15) | 0.075 (5)* | |
H7B | 0.506 (3) | 0.666 (3) | 0.4655 (18) | 0.105 (7)* | |
C7A | 0.48096 (17) | 0.71261 (18) | 0.32495 (14) | 0.0569 (4) | |
C8 | 0.7693 (3) | 0.9629 (2) | 0.4771 (2) | 0.0795 (6) | |
H8A | 0.866 (3) | 0.994 (3) | 0.515 (2) | 0.131 (10)* | |
H8B | 0.717 (2) | 1.032 (3) | 0.5270 (19) | 0.099 (7)* | |
H8C | 0.769 (3) | 0.970 (3) | 0.395 (3) | 0.142 (10)* | |
C9 | 0.7390 (3) | 0.8095 (4) | 0.58442 (18) | 0.0905 (7) | |
H9A | 0.691 (3) | 0.871 (3) | 0.640 (2) | 0.108 (8)* | |
H9B | 0.690 (2) | 0.707 (2) | 0.5803 (15) | 0.073 (6)* | |
H9C | 0.854 (3) | 0.847 (3) | 0.601 (2) | 0.116 (8)* | |
C10 | 0.3231 (2) | 0.6199 (3) | 0.3118 (2) | 0.0845 (7) | |
H10A | 0.285 (2) | 0.595 (2) | 0.2259 (18) | 0.088 (6)* | |
H10B | 0.332 (3) | 0.531 (3) | 0.3350 (19) | 0.110 (8)* | |
H10C | 0.265 (3) | 0.670 (3) | 0.364 (2) | 0.128 (9)* | |
C11 | 0.90549 (16) | 0.79953 (16) | 0.08717 (12) | 0.0482 (4) | |
C12 | 0.8562 (2) | 0.7225 (2) | −0.01941 (14) | 0.0609 (5) | |
H12 | 0.8596 (17) | 0.6267 (19) | −0.0494 (13) | 0.055 (5)* | |
C13 | 0.7921 (2) | 0.7817 (2) | −0.07940 (18) | 0.0727 (6) | |
H13 | 0.764 (2) | 0.736 (2) | −0.1512 (18) | 0.083 (6)* | |
C14 | 0.7768 (2) | 0.9159 (2) | −0.03698 (17) | 0.0667 (5) | |
C15 | 0.8293 (2) | 0.9915 (2) | 0.06906 (18) | 0.0682 (5) | |
H15 | 0.8218 (19) | 1.081 (2) | 0.0985 (14) | 0.066 (5)* | |
C16 | 0.8932 (2) | 0.93484 (19) | 0.13092 (16) | 0.0590 (4) | |
H16 | 0.9303 (17) | 0.9868 (18) | 0.2063 (15) | 0.055 (5)* | |
C17 | 0.7039 (4) | 0.9782 (4) | −0.1027 (3) | 0.1019 (9) | |
H17A | 0.738 (4) | 1.083 (4) | −0.075 (3) | 0.149 (12)* | |
H17B | 0.611 (4) | 0.978 (3) | −0.089 (2) | 0.135 (11)* | |
H17C | 0.746 (3) | 0.978 (3) | −0.164 (3) | 0.141 (12)* | |
C21 | 0.80339 (19) | 0.39685 (16) | 0.22066 (14) | 0.0561 (4) | |
C22 | 0.6842 (3) | 0.3001 (2) | 0.2344 (2) | 0.0826 (7) | |
H22 | 0.599 (3) | 0.285 (2) | 0.1897 (18) | 0.089 (8)* | |
C23 | 0.6956 (5) | 0.2342 (3) | 0.3060 (3) | 0.1183 (11) | |
H23 | 0.606 (3) | 0.169 (3) | 0.309 (2) | 0.132 (10)* | |
C24 | 0.8240 (6) | 0.2628 (4) | 0.3639 (3) | 0.1281 (14) | |
H24 | 0.837 (3) | 0.225 (3) | 0.411 (2) | 0.138 (11)* | |
C25 | 0.9444 (4) | 0.3572 (4) | 0.3514 (3) | 0.1108 (9) | |
H25 | 1.024 (3) | 0.387 (3) | 0.392 (2) | 0.112 (11)* | |
C26 | 0.9339 (3) | 0.4236 (2) | 0.28023 (19) | 0.0781 (6) | |
H26 | 1.010 (3) | 0.483 (3) | 0.2678 (19) | 0.099 (8)* | |
C27 | 0.7918 (2) | 0.47321 (17) | 0.14481 (14) | 0.0534 (4) | |
H27A | 0.8565 (18) | 0.4509 (18) | 0.0897 (14) | 0.057 (5)* | |
H27B | 0.689 (2) | 0.4430 (17) | 0.1108 (13) | 0.056 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0440 (2) | 0.0505 (3) | 0.0478 (3) | 0.01175 (18) | 0.00793 (17) | 0.01307 (19) |
O1 | 0.0535 (6) | 0.0687 (8) | 0.0658 (7) | 0.0245 (6) | 0.0199 (6) | 0.0203 (6) |
O2 | 0.0544 (6) | 0.0618 (7) | 0.0537 (7) | 0.0031 (6) | −0.0020 (5) | 0.0108 (6) |
N1 | 0.0499 (7) | 0.0400 (7) | 0.0466 (7) | 0.0149 (6) | 0.0135 (6) | 0.0112 (6) |
C1 | 0.0676 (13) | 0.0782 (14) | 0.0862 (16) | 0.0354 (12) | 0.0038 (11) | 0.0265 (12) |
C2 | 0.0763 (14) | 0.1122 (19) | 0.0866 (17) | 0.0376 (14) | 0.0080 (13) | 0.0491 (15) |
C3 | 0.0564 (11) | 0.0932 (15) | 0.0540 (11) | 0.0190 (11) | 0.0015 (9) | 0.0177 (10) |
C3A | 0.0474 (9) | 0.0484 (10) | 0.0512 (10) | 0.0138 (8) | 0.0039 (7) | 0.0104 (8) |
C4 | 0.0433 (8) | 0.0413 (9) | 0.0416 (8) | 0.0152 (7) | 0.0063 (6) | 0.0112 (7) |
C5 | 0.0567 (11) | 0.0646 (12) | 0.0464 (10) | 0.0268 (9) | 0.0082 (8) | 0.0181 (8) |
C6 | 0.0586 (10) | 0.0752 (12) | 0.0457 (9) | 0.0244 (9) | 0.0058 (8) | 0.0133 (9) |
C7 | 0.0606 (11) | 0.0803 (13) | 0.0555 (11) | 0.0226 (10) | 0.0162 (9) | 0.0137 (10) |
C7A | 0.0419 (8) | 0.0627 (11) | 0.0621 (10) | 0.0175 (8) | 0.0086 (8) | 0.0137 (9) |
C8 | 0.0778 (14) | 0.0637 (13) | 0.0763 (15) | 0.0180 (12) | 0.0037 (12) | −0.0023 (11) |
C9 | 0.0959 (18) | 0.122 (2) | 0.0495 (12) | 0.0383 (18) | 0.0092 (12) | 0.0177 (13) |
C10 | 0.0521 (11) | 0.1027 (18) | 0.0877 (17) | 0.0144 (11) | 0.0177 (11) | 0.0228 (15) |
C11 | 0.0480 (8) | 0.0456 (9) | 0.0475 (9) | 0.0081 (7) | 0.0099 (7) | 0.0145 (7) |
C12 | 0.0705 (11) | 0.0542 (11) | 0.0526 (11) | 0.0113 (9) | 0.0054 (9) | 0.0148 (9) |
C13 | 0.0800 (13) | 0.0802 (15) | 0.0530 (12) | 0.0105 (11) | −0.0026 (10) | 0.0237 (11) |
C14 | 0.0611 (11) | 0.0771 (13) | 0.0752 (13) | 0.0162 (10) | 0.0135 (10) | 0.0440 (12) |
C15 | 0.0755 (12) | 0.0556 (12) | 0.0824 (15) | 0.0236 (10) | 0.0219 (11) | 0.0302 (11) |
C16 | 0.0685 (11) | 0.0503 (10) | 0.0558 (11) | 0.0131 (9) | 0.0116 (9) | 0.0169 (9) |
C17 | 0.0863 (18) | 0.131 (3) | 0.124 (2) | 0.0329 (18) | 0.0122 (18) | 0.086 (2) |
C21 | 0.0582 (10) | 0.0390 (9) | 0.0711 (11) | 0.0192 (8) | 0.0240 (9) | 0.0143 (8) |
C22 | 0.0796 (15) | 0.0508 (11) | 0.1142 (18) | 0.0130 (11) | 0.0368 (14) | 0.0271 (13) |
C23 | 0.144 (3) | 0.0729 (17) | 0.156 (3) | 0.032 (2) | 0.081 (3) | 0.060 (2) |
C24 | 0.204 (4) | 0.104 (2) | 0.131 (3) | 0.082 (3) | 0.074 (3) | 0.079 (2) |
C25 | 0.133 (3) | 0.106 (2) | 0.127 (2) | 0.057 (2) | 0.012 (2) | 0.063 (2) |
C26 | 0.0730 (14) | 0.0725 (13) | 0.1066 (17) | 0.0278 (11) | 0.0153 (12) | 0.0475 (13) |
C27 | 0.0519 (10) | 0.0437 (9) | 0.0555 (10) | 0.0138 (8) | 0.0103 (9) | 0.0044 (8) |
S1—O2 | 1.4288 (12) | C9—H9A | 1.00 (3) |
S1—O1 | 1.4302 (12) | C9—H9B | 1.05 (2) |
S1—N1 | 1.6227 (12) | C9—H9C | 1.06 (3) |
S1—C11 | 1.7639 (17) | C10—H10A | 1.12 (2) |
N1—C27 | 1.467 (2) | C10—H10B | 1.11 (3) |
N1—C4 | 1.4902 (18) | C10—H10C | 0.98 (3) |
C1—C2 | 1.503 (3) | C11—C16 | 1.382 (2) |
C1—C7A | 1.548 (3) | C11—C12 | 1.388 (2) |
C1—H1A | 1.01 (2) | C12—C13 | 1.379 (3) |
C1—H1B | 0.99 (2) | C12—H12 | 0.961 (18) |
C2—C3 | 1.530 (3) | C13—C14 | 1.380 (3) |
C2—H2A | 1.00 (3) | C13—H13 | 0.92 (2) |
C2—H2B | 0.99 (3) | C14—C15 | 1.385 (3) |
C3—C3A | 1.518 (3) | C14—C17 | 1.504 (3) |
C3—H3A | 0.97 (2) | C15—C16 | 1.376 (3) |
C3—H3B | 1.14 (2) | C15—H15 | 0.91 (2) |
C3A—C4 | 1.535 (2) | C16—H16 | 0.982 (18) |
C3A—C7A | 1.550 (2) | C17—H17A | 1.01 (4) |
C3A—H3AA | 0.987 (16) | C17—H17B | 0.90 (3) |
C4—C5 | 1.520 (2) | C17—H17C | 0.91 (3) |
C4—H4 | 0.964 (15) | C21—C26 | 1.376 (3) |
C5—C6 | 1.539 (2) | C21—C22 | 1.380 (3) |
C5—H5A | 0.950 (19) | C21—C27 | 1.504 (2) |
C5—H5B | 1.018 (17) | C22—C23 | 1.370 (5) |
C6—C9 | 1.516 (3) | C22—H22 | 0.95 (2) |
C6—C7 | 1.539 (3) | C23—C24 | 1.345 (5) |
C6—C8 | 1.541 (3) | C23—H23 | 0.96 (3) |
C7—C7A | 1.532 (3) | C24—C25 | 1.367 (5) |
C7—H7A | 1.06 (2) | C24—H24 | 0.87 (3) |
C7—H7B | 1.09 (3) | C25—C26 | 1.368 (4) |
C7A—C10 | 1.541 (3) | C25—H25 | 0.85 (3) |
C8—H8A | 0.97 (3) | C26—H26 | 0.89 (2) |
C8—H8B | 1.03 (3) | C27—H27A | 0.955 (17) |
C8—H8C | 1.12 (3) | C27—H27B | 0.997 (17) |
O2—S1—O1 | 119.41 (7) | H8A—C8—H8B | 101 (2) |
O2—S1—N1 | 108.21 (6) | C6—C8—H8C | 111.7 (15) |
O1—S1—N1 | 107.65 (7) | H8A—C8—H8C | 114 (2) |
O2—S1—C11 | 106.66 (7) | H8B—C8—H8C | 111 (2) |
O1—S1—C11 | 108.58 (7) | C6—C9—H9A | 112.3 (14) |
N1—S1—C11 | 105.52 (7) | C6—C9—H9B | 105.3 (11) |
C27—N1—C4 | 121.43 (12) | H9A—C9—H9B | 107.0 (17) |
C27—N1—S1 | 121.30 (10) | C6—C9—H9C | 105.1 (14) |
C4—N1—S1 | 117.04 (9) | H9A—C9—H9C | 109 (2) |
C2—C1—C7A | 106.16 (18) | H9B—C9—H9C | 118.2 (18) |
C2—C1—H1A | 107.2 (12) | C7A—C10—H10A | 104.2 (10) |
C7A—C1—H1A | 111.0 (13) | C7A—C10—H10B | 105.9 (13) |
C2—C1—H1B | 116.4 (13) | H10A—C10—H10B | 115.9 (17) |
C7A—C1—H1B | 109.7 (12) | C7A—C10—H10C | 109.3 (16) |
H1A—C1—H1B | 106.4 (18) | H10A—C10—H10C | 115.0 (19) |
C1—C2—C3 | 106.79 (18) | H10B—C10—H10C | 106.1 (19) |
C1—C2—H2A | 107.5 (16) | C16—C11—C12 | 119.91 (17) |
C3—C2—H2A | 107.4 (17) | C16—C11—S1 | 120.10 (13) |
C1—C2—H2B | 115.0 (19) | C12—C11—S1 | 119.93 (13) |
C3—C2—H2B | 107.2 (19) | C13—C12—C11 | 119.08 (19) |
H2A—C2—H2B | 113 (2) | C13—C12—H12 | 120.4 (10) |
C3A—C3—C2 | 106.62 (17) | C11—C12—H12 | 120.4 (10) |
C3A—C3—H3A | 110.3 (12) | C12—C13—C14 | 122.0 (2) |
C2—C3—H3A | 110.4 (13) | C12—C13—H13 | 121.4 (13) |
C3A—C3—H3B | 106.4 (11) | C14—C13—H13 | 116.4 (13) |
C2—C3—H3B | 113.2 (11) | C13—C14—C15 | 117.73 (19) |
H3A—C3—H3B | 109.8 (17) | C13—C14—C17 | 121.4 (2) |
C3—C3A—C4 | 113.58 (15) | C15—C14—C17 | 120.8 (2) |
C3—C3A—C7A | 103.60 (14) | C16—C15—C14 | 121.51 (19) |
C4—C3A—C7A | 111.14 (13) | C16—C15—H15 | 119.2 (12) |
C3—C3A—H3AA | 110.3 (9) | C14—C15—H15 | 119.3 (12) |
C4—C3A—H3AA | 108.7 (9) | C15—C16—C11 | 119.74 (19) |
C7A—C3A—H3AA | 109.3 (9) | C15—C16—H16 | 122.5 (10) |
N1—C4—C5 | 112.47 (12) | C11—C16—H16 | 117.8 (10) |
N1—C4—C3A | 112.84 (12) | C14—C17—H17A | 111.5 (19) |
C5—C4—C3A | 111.56 (13) | C14—C17—H17B | 113.1 (19) |
N1—C4—H4 | 103.9 (8) | H17A—C17—H17B | 93 (3) |
C5—C4—H4 | 109.7 (8) | C14—C17—H17C | 114 (2) |
C3A—C4—H4 | 105.8 (8) | H17A—C17—H17C | 88 (2) |
C4—C5—C6 | 112.32 (14) | H17B—C17—H17C | 128 (3) |
C4—C5—H5A | 107.5 (11) | C26—C21—C22 | 117.8 (2) |
C6—C5—H5A | 111.2 (10) | C26—C21—C27 | 120.53 (16) |
C4—C5—H5B | 115.6 (9) | C22—C21—C27 | 121.6 (2) |
C6—C5—H5B | 105.9 (9) | C23—C22—C21 | 120.9 (3) |
H5A—C5—H5B | 104.1 (14) | C23—C22—H22 | 125.6 (14) |
C9—C6—C5 | 109.56 (18) | C21—C22—H22 | 113.5 (14) |
C9—C6—C7 | 108.78 (17) | C24—C23—C22 | 120.2 (3) |
C5—C6—C7 | 107.41 (15) | C24—C23—H23 | 125.7 (18) |
C9—C6—C8 | 107.2 (2) | C22—C23—H23 | 114.1 (18) |
C5—C6—C8 | 110.80 (16) | C23—C24—C25 | 120.2 (3) |
C7—C6—C8 | 113.02 (18) | C23—C24—H24 | 124 (2) |
C7A—C7—C6 | 119.55 (14) | C25—C24—H24 | 115 (2) |
C7A—C7—H7A | 108.6 (10) | C24—C25—C26 | 119.9 (3) |
C6—C7—H7A | 108.1 (10) | C24—C25—H25 | 123 (2) |
C7A—C7—H7B | 105.7 (12) | C26—C25—H25 | 116 (2) |
C6—C7—H7B | 105.4 (12) | C25—C26—C21 | 120.9 (3) |
H7A—C7—H7B | 109.2 (16) | C25—C26—H26 | 122.8 (15) |
C7—C7A—C10 | 107.94 (16) | C21—C26—H26 | 116.2 (15) |
C7—C7A—C1 | 116.03 (17) | N1—C27—C21 | 112.26 (14) |
C10—C7A—C1 | 107.65 (18) | N1—C27—H27A | 107.6 (10) |
C7—C7A—C3A | 113.88 (14) | C21—C27—H27A | 109.4 (10) |
C10—C7A—C3A | 109.02 (16) | N1—C27—H27B | 109.7 (10) |
C1—C7A—C3A | 101.98 (14) | C21—C27—H27B | 109.3 (9) |
C6—C8—H8A | 106.0 (17) | H27A—C27—H27B | 108.6 (14) |
C6—C8—H8B | 113.3 (12) | ||
O2—S1—N1—C27 | −143.34 (13) | C4—C3A—C7A—C7 | −41.7 (2) |
O1—S1—N1—C27 | −13.02 (15) | C3—C3A—C7A—C10 | 75.4 (2) |
C11—S1—N1—C27 | 102.79 (13) | C4—C3A—C7A—C10 | −162.30 (17) |
O2—S1—N1—C4 | 42.17 (12) | C3—C3A—C7A—C1 | −38.26 (18) |
O1—S1—N1—C4 | 172.49 (10) | C4—C3A—C7A—C1 | 84.06 (17) |
C11—S1—N1—C4 | −71.70 (12) | O2—S1—C11—C16 | −14.60 (15) |
C7A—C1—C2—C3 | −16.1 (2) | O1—S1—C11—C16 | −144.48 (13) |
C1—C2—C3—C3A | −8.4 (2) | N1—S1—C11—C16 | 100.35 (14) |
C2—C3—C3A—C4 | −91.4 (2) | O2—S1—C11—C12 | 168.15 (13) |
C2—C3—C3A—C7A | 29.3 (2) | O1—S1—C11—C12 | 38.27 (15) |
C27—N1—C4—C5 | 91.02 (18) | N1—S1—C11—C12 | −76.90 (14) |
S1—N1—C4—C5 | −94.50 (15) | C16—C11—C12—C13 | −1.6 (3) |
C27—N1—C4—C3A | −36.25 (19) | S1—C11—C12—C13 | 175.67 (13) |
S1—N1—C4—C3A | 138.22 (12) | C11—C12—C13—C14 | 0.7 (3) |
C3—C3A—C4—N1 | −61.53 (19) | C12—C13—C14—C15 | 0.5 (3) |
C7A—C3A—C4—N1 | −177.87 (12) | C12—C13—C14—C17 | −178.8 (2) |
C3—C3A—C4—C5 | 170.72 (16) | C13—C14—C15—C16 | −0.7 (3) |
C7A—C3A—C4—C5 | 54.37 (19) | C17—C14—C15—C16 | 178.5 (2) |
N1—C4—C5—C6 | 168.18 (13) | C14—C15—C16—C11 | −0.2 (3) |
C3A—C4—C5—C6 | −63.9 (2) | C12—C11—C16—C15 | 1.3 (2) |
C4—C5—C6—C9 | 173.61 (18) | S1—C11—C16—C15 | −175.91 (13) |
C4—C5—C6—C7 | 55.6 (2) | C26—C21—C22—C23 | 0.7 (3) |
C4—C5—C6—C8 | −68.3 (2) | C27—C21—C22—C23 | −178.2 (2) |
C9—C6—C7—C7A | −163.4 (2) | C21—C22—C23—C24 | −0.2 (4) |
C5—C6—C7—C7A | −44.9 (2) | C22—C23—C24—C25 | −0.4 (5) |
C8—C6—C7—C7A | 77.6 (2) | C23—C24—C25—C26 | 0.5 (5) |
C6—C7—C7A—C10 | 160.8 (2) | C24—C25—C26—C21 | 0.0 (4) |
C6—C7—C7A—C1 | −78.3 (2) | C22—C21—C26—C25 | −0.6 (3) |
C6—C7—C7A—C3A | 39.6 (3) | C27—C21—C26—C25 | 178.4 (2) |
C2—C1—C7A—C7 | 157.96 (17) | C4—N1—C27—C21 | −70.10 (18) |
C2—C1—C7A—C10 | −81.0 (2) | S1—N1—C27—C21 | 115.66 (14) |
C2—C1—C7A—C3A | 33.6 (2) | C26—C21—C27—N1 | −56.0 (2) |
C3—C3A—C7A—C7 | −164.04 (17) | C22—C21—C27—N1 | 122.83 (18) |
Experimental details
Crystal data | |
Chemical formula | C26H35NO2S |
Mr | 425.61 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 291 |
a, b, c (Å) | 9.3965 (2), 10.5437 (3), 13.2813 (4) |
α, β, γ (°) | 109.6116 (16), 90.009 (2), 103.902 (2) |
V (Å3) | 1198.48 (6) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.16 |
Crystal size (mm) | 0.30 × 0.10 × 0.10 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13129, 5198, 3347 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.648 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.123, 1.00 |
No. of reflections | 5198 |
No. of parameters | 411 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.23, −0.23 |
Computer programs: COLLECT (Nonius, 1998), DENZO and SCALEPACK (Otwinowski & Minor, 1997), DENZO and SCALEPACK, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXL97.
No Comment.