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The synthesis, spectroscopic data and X-ray structural analysis of the title compound, C26H35NO2S, (I), are described. The crystal contains discrete mol­ecules separated by normal van der Waals distances. The benzene­sulfon­amide derivative of the corresponding amine allows the assigment of its relative configuration. The secondary amine has been synthesized via a sequential multi-step hydro­formyl­ation procedure according to Eilbracht et al. [Chem. Rev. (1999), 99, 3329-3365].).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100009148/qa0340sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100009148/qa0340Isup2.hkl
Contains datablock I

CCDC reference: 150393

Comment top

No Comment.

Experimental top

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.

Refinement top

All H atoms were located in a difference electron-density map and refined isotropically; C—H 0.85 (3)–1.14 (2) Å.

Computing details top

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.

(I) top
Crystal data top
C26H35NO2SZ = 2
Mr = 425.61F(000) = 460
Triclinic, P1Dx = 1.179 Mg m3
a = 9.3965 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.5437 (3) ÅCell parameters from 13129 reflections
c = 13.2813 (4) Åθ = 3.2–27.4°
α = 109.6116 (16)°µ = 0.16 mm1
β = 90.009 (2)°T = 291 K
γ = 103.902 (2)°Needle, colourless
V = 1198.48 (6) Å30.30 × 0.10 × 0.10 mm
Data collection top
Nonius KappaCCD
diffractometer
3347 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.028
Graphite monochromatorθmax = 27.4°, θmin = 3.2°
Detector resolution: 10 vertical, 18 horizontal pixels mm-1h = 1212
358 frames via ω–rotation (Δω = 1°) and two times 60 s per frame with four sets at different κ angles scansk = 1313
13129 measured reflectionsl = 1717
5198 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: difference Fourier map
wR(F2) = 0.123All H-atom parameters refined
S = 1.00Calculated w = 1/[σ2(Fo2) + (0.0746P)2]
where P = (Fo2 + 2Fc2)/3
5198 reflections(Δ/σ)max = 0.001
411 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.23 e Å3
Crystal data top
C26H35NO2Sγ = 103.902 (2)°
Mr = 425.61V = 1198.48 (6) Å3
Triclinic, P1Z = 2
a = 9.3965 (2) ÅMo Kα radiation
b = 10.5437 (3) ŵ = 0.16 mm1
c = 13.2813 (4) ÅT = 291 K
α = 109.6116 (16)°0.30 × 0.10 × 0.10 mm
β = 90.009 (2)°
Data collection top
Nonius KappaCCD
diffractometer
3347 reflections with I > 2σ(I)
13129 measured reflectionsRint = 0.028
5198 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.123All H-atom parameters refined
S = 1.00Δρmax = 0.23 e Å3
5198 reflectionsΔρmin = 0.23 e Å3
411 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.97632 (4)0.72220 (4)0.16808 (3)0.04853 (16)
O11.06036 (12)0.63284 (13)0.10469 (9)0.0618 (3)
O21.04502 (12)0.83254 (12)0.26418 (9)0.0612 (3)
N10.83376 (13)0.62486 (12)0.19873 (10)0.0459 (3)
C10.4754 (3)0.8308 (2)0.28181 (19)0.0748 (6)
H1A0.567 (3)0.910 (2)0.3082 (17)0.093 (7)*
H1B0.392 (3)0.870 (2)0.3094 (17)0.095 (7)*
C20.4740 (3)0.7697 (3)0.1619 (2)0.0854 (7)
H2A0.370 (3)0.744 (3)0.131 (2)0.129 (9)*
H2B0.542 (4)0.829 (3)0.129 (3)0.160 (12)*
C30.5231 (2)0.6350 (3)0.13749 (16)0.0699 (5)
H3A0.603 (2)0.634 (2)0.0908 (16)0.084 (6)*
H3B0.430 (3)0.537 (2)0.1003 (18)0.102 (7)*
C3A0.57458 (17)0.63101 (18)0.24445 (13)0.0505 (4)
H3AA0.5517 (16)0.5341 (18)0.2433 (12)0.049 (4)*
C40.73978 (16)0.69718 (17)0.27638 (12)0.0421 (3)
H40.7585 (15)0.7880 (16)0.2698 (11)0.039 (4)*
C50.7813 (2)0.7121 (2)0.39118 (13)0.0541 (4)
H5A0.7545 (19)0.622 (2)0.3961 (13)0.061 (5)*
H5B0.8909 (19)0.7469 (17)0.4152 (12)0.053 (4)*
C60.70714 (18)0.8120 (2)0.47333 (13)0.0605 (5)
C70.5401 (2)0.7586 (2)0.44260 (15)0.0672 (5)
H7A0.489 (2)0.836 (2)0.4892 (15)0.075 (5)*
H7B0.506 (3)0.666 (3)0.4655 (18)0.105 (7)*
C7A0.48096 (17)0.71261 (18)0.32495 (14)0.0569 (4)
C80.7693 (3)0.9629 (2)0.4771 (2)0.0795 (6)
H8A0.866 (3)0.994 (3)0.515 (2)0.131 (10)*
H8B0.717 (2)1.032 (3)0.5270 (19)0.099 (7)*
H8C0.769 (3)0.970 (3)0.395 (3)0.142 (10)*
C90.7390 (3)0.8095 (4)0.58442 (18)0.0905 (7)
H9A0.691 (3)0.871 (3)0.640 (2)0.108 (8)*
H9B0.690 (2)0.707 (2)0.5803 (15)0.073 (6)*
H9C0.854 (3)0.847 (3)0.601 (2)0.116 (8)*
C100.3231 (2)0.6199 (3)0.3118 (2)0.0845 (7)
H10A0.285 (2)0.595 (2)0.2259 (18)0.088 (6)*
H10B0.332 (3)0.531 (3)0.3350 (19)0.110 (8)*
H10C0.265 (3)0.670 (3)0.364 (2)0.128 (9)*
C110.90549 (16)0.79953 (16)0.08717 (12)0.0482 (4)
C120.8562 (2)0.7225 (2)0.01941 (14)0.0609 (5)
H120.8596 (17)0.6267 (19)0.0494 (13)0.055 (5)*
C130.7921 (2)0.7817 (2)0.07940 (18)0.0727 (6)
H130.764 (2)0.736 (2)0.1512 (18)0.083 (6)*
C140.7768 (2)0.9159 (2)0.03698 (17)0.0667 (5)
C150.8293 (2)0.9915 (2)0.06906 (18)0.0682 (5)
H150.8218 (19)1.081 (2)0.0985 (14)0.066 (5)*
C160.8932 (2)0.93484 (19)0.13092 (16)0.0590 (4)
H160.9303 (17)0.9868 (18)0.2063 (15)0.055 (5)*
C170.7039 (4)0.9782 (4)0.1027 (3)0.1019 (9)
H17A0.738 (4)1.083 (4)0.075 (3)0.149 (12)*
H17B0.611 (4)0.978 (3)0.089 (2)0.135 (11)*
H17C0.746 (3)0.978 (3)0.164 (3)0.141 (12)*
C210.80339 (19)0.39685 (16)0.22066 (14)0.0561 (4)
C220.6842 (3)0.3001 (2)0.2344 (2)0.0826 (7)
H220.599 (3)0.285 (2)0.1897 (18)0.089 (8)*
C230.6956 (5)0.2342 (3)0.3060 (3)0.1183 (11)
H230.606 (3)0.169 (3)0.309 (2)0.132 (10)*
C240.8240 (6)0.2628 (4)0.3639 (3)0.1281 (14)
H240.837 (3)0.225 (3)0.411 (2)0.138 (11)*
C250.9444 (4)0.3572 (4)0.3514 (3)0.1108 (9)
H251.024 (3)0.387 (3)0.392 (2)0.112 (11)*
C260.9339 (3)0.4236 (2)0.28023 (19)0.0781 (6)
H261.010 (3)0.483 (3)0.2678 (19)0.099 (8)*
C270.7918 (2)0.47321 (17)0.14481 (14)0.0534 (4)
H27A0.8565 (18)0.4509 (18)0.0897 (14)0.057 (5)*
H27B0.689 (2)0.4430 (17)0.1108 (13)0.056 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0440 (2)0.0505 (3)0.0478 (3)0.01175 (18)0.00793 (17)0.01307 (19)
O10.0535 (6)0.0687 (8)0.0658 (7)0.0245 (6)0.0199 (6)0.0203 (6)
O20.0544 (6)0.0618 (7)0.0537 (7)0.0031 (6)0.0020 (5)0.0108 (6)
N10.0499 (7)0.0400 (7)0.0466 (7)0.0149 (6)0.0135 (6)0.0112 (6)
C10.0676 (13)0.0782 (14)0.0862 (16)0.0354 (12)0.0038 (11)0.0265 (12)
C20.0763 (14)0.1122 (19)0.0866 (17)0.0376 (14)0.0080 (13)0.0491 (15)
C30.0564 (11)0.0932 (15)0.0540 (11)0.0190 (11)0.0015 (9)0.0177 (10)
C3A0.0474 (9)0.0484 (10)0.0512 (10)0.0138 (8)0.0039 (7)0.0104 (8)
C40.0433 (8)0.0413 (9)0.0416 (8)0.0152 (7)0.0063 (6)0.0112 (7)
C50.0567 (11)0.0646 (12)0.0464 (10)0.0268 (9)0.0082 (8)0.0181 (8)
C60.0586 (10)0.0752 (12)0.0457 (9)0.0244 (9)0.0058 (8)0.0133 (9)
C70.0606 (11)0.0803 (13)0.0555 (11)0.0226 (10)0.0162 (9)0.0137 (10)
C7A0.0419 (8)0.0627 (11)0.0621 (10)0.0175 (8)0.0086 (8)0.0137 (9)
C80.0778 (14)0.0637 (13)0.0763 (15)0.0180 (12)0.0037 (12)0.0023 (11)
C90.0959 (18)0.122 (2)0.0495 (12)0.0383 (18)0.0092 (12)0.0177 (13)
C100.0521 (11)0.1027 (18)0.0877 (17)0.0144 (11)0.0177 (11)0.0228 (15)
C110.0480 (8)0.0456 (9)0.0475 (9)0.0081 (7)0.0099 (7)0.0145 (7)
C120.0705 (11)0.0542 (11)0.0526 (11)0.0113 (9)0.0054 (9)0.0148 (9)
C130.0800 (13)0.0802 (15)0.0530 (12)0.0105 (11)0.0026 (10)0.0237 (11)
C140.0611 (11)0.0771 (13)0.0752 (13)0.0162 (10)0.0135 (10)0.0440 (12)
C150.0755 (12)0.0556 (12)0.0824 (15)0.0236 (10)0.0219 (11)0.0302 (11)
C160.0685 (11)0.0503 (10)0.0558 (11)0.0131 (9)0.0116 (9)0.0169 (9)
C170.0863 (18)0.131 (3)0.124 (2)0.0329 (18)0.0122 (18)0.086 (2)
C210.0582 (10)0.0390 (9)0.0711 (11)0.0192 (8)0.0240 (9)0.0143 (8)
C220.0796 (15)0.0508 (11)0.1142 (18)0.0130 (11)0.0368 (14)0.0271 (13)
C230.144 (3)0.0729 (17)0.156 (3)0.032 (2)0.081 (3)0.060 (2)
C240.204 (4)0.104 (2)0.131 (3)0.082 (3)0.074 (3)0.079 (2)
C250.133 (3)0.106 (2)0.127 (2)0.057 (2)0.012 (2)0.063 (2)
C260.0730 (14)0.0725 (13)0.1066 (17)0.0278 (11)0.0153 (12)0.0475 (13)
C270.0519 (10)0.0437 (9)0.0555 (10)0.0138 (8)0.0103 (9)0.0044 (8)
Geometric parameters (Å, º) top
S1—O21.4288 (12)C9—H9A1.00 (3)
S1—O11.4302 (12)C9—H9B1.05 (2)
S1—N11.6227 (12)C9—H9C1.06 (3)
S1—C111.7639 (17)C10—H10A1.12 (2)
N1—C271.467 (2)C10—H10B1.11 (3)
N1—C41.4902 (18)C10—H10C0.98 (3)
C1—C21.503 (3)C11—C161.382 (2)
C1—C7A1.548 (3)C11—C121.388 (2)
C1—H1A1.01 (2)C12—C131.379 (3)
C1—H1B0.99 (2)C12—H120.961 (18)
C2—C31.530 (3)C13—C141.380 (3)
C2—H2A1.00 (3)C13—H130.92 (2)
C2—H2B0.99 (3)C14—C151.385 (3)
C3—C3A1.518 (3)C14—C171.504 (3)
C3—H3A0.97 (2)C15—C161.376 (3)
C3—H3B1.14 (2)C15—H150.91 (2)
C3A—C41.535 (2)C16—H160.982 (18)
C3A—C7A1.550 (2)C17—H17A1.01 (4)
C3A—H3AA0.987 (16)C17—H17B0.90 (3)
C4—C51.520 (2)C17—H17C0.91 (3)
C4—H40.964 (15)C21—C261.376 (3)
C5—C61.539 (2)C21—C221.380 (3)
C5—H5A0.950 (19)C21—C271.504 (2)
C5—H5B1.018 (17)C22—C231.370 (5)
C6—C91.516 (3)C22—H220.95 (2)
C6—C71.539 (3)C23—C241.345 (5)
C6—C81.541 (3)C23—H230.96 (3)
C7—C7A1.532 (3)C24—C251.367 (5)
C7—H7A1.06 (2)C24—H240.87 (3)
C7—H7B1.09 (3)C25—C261.368 (4)
C7A—C101.541 (3)C25—H250.85 (3)
C8—H8A0.97 (3)C26—H260.89 (2)
C8—H8B1.03 (3)C27—H27A0.955 (17)
C8—H8C1.12 (3)C27—H27B0.997 (17)
O2—S1—O1119.41 (7)H8A—C8—H8B101 (2)
O2—S1—N1108.21 (6)C6—C8—H8C111.7 (15)
O1—S1—N1107.65 (7)H8A—C8—H8C114 (2)
O2—S1—C11106.66 (7)H8B—C8—H8C111 (2)
O1—S1—C11108.58 (7)C6—C9—H9A112.3 (14)
N1—S1—C11105.52 (7)C6—C9—H9B105.3 (11)
C27—N1—C4121.43 (12)H9A—C9—H9B107.0 (17)
C27—N1—S1121.30 (10)C6—C9—H9C105.1 (14)
C4—N1—S1117.04 (9)H9A—C9—H9C109 (2)
C2—C1—C7A106.16 (18)H9B—C9—H9C118.2 (18)
C2—C1—H1A107.2 (12)C7A—C10—H10A104.2 (10)
C7A—C1—H1A111.0 (13)C7A—C10—H10B105.9 (13)
C2—C1—H1B116.4 (13)H10A—C10—H10B115.9 (17)
C7A—C1—H1B109.7 (12)C7A—C10—H10C109.3 (16)
H1A—C1—H1B106.4 (18)H10A—C10—H10C115.0 (19)
C1—C2—C3106.79 (18)H10B—C10—H10C106.1 (19)
C1—C2—H2A107.5 (16)C16—C11—C12119.91 (17)
C3—C2—H2A107.4 (17)C16—C11—S1120.10 (13)
C1—C2—H2B115.0 (19)C12—C11—S1119.93 (13)
C3—C2—H2B107.2 (19)C13—C12—C11119.08 (19)
H2A—C2—H2B113 (2)C13—C12—H12120.4 (10)
C3A—C3—C2106.62 (17)C11—C12—H12120.4 (10)
C3A—C3—H3A110.3 (12)C12—C13—C14122.0 (2)
C2—C3—H3A110.4 (13)C12—C13—H13121.4 (13)
C3A—C3—H3B106.4 (11)C14—C13—H13116.4 (13)
C2—C3—H3B113.2 (11)C13—C14—C15117.73 (19)
H3A—C3—H3B109.8 (17)C13—C14—C17121.4 (2)
C3—C3A—C4113.58 (15)C15—C14—C17120.8 (2)
C3—C3A—C7A103.60 (14)C16—C15—C14121.51 (19)
C4—C3A—C7A111.14 (13)C16—C15—H15119.2 (12)
C3—C3A—H3AA110.3 (9)C14—C15—H15119.3 (12)
C4—C3A—H3AA108.7 (9)C15—C16—C11119.74 (19)
C7A—C3A—H3AA109.3 (9)C15—C16—H16122.5 (10)
N1—C4—C5112.47 (12)C11—C16—H16117.8 (10)
N1—C4—C3A112.84 (12)C14—C17—H17A111.5 (19)
C5—C4—C3A111.56 (13)C14—C17—H17B113.1 (19)
N1—C4—H4103.9 (8)H17A—C17—H17B93 (3)
C5—C4—H4109.7 (8)C14—C17—H17C114 (2)
C3A—C4—H4105.8 (8)H17A—C17—H17C88 (2)
C4—C5—C6112.32 (14)H17B—C17—H17C128 (3)
C4—C5—H5A107.5 (11)C26—C21—C22117.8 (2)
C6—C5—H5A111.2 (10)C26—C21—C27120.53 (16)
C4—C5—H5B115.6 (9)C22—C21—C27121.6 (2)
C6—C5—H5B105.9 (9)C23—C22—C21120.9 (3)
H5A—C5—H5B104.1 (14)C23—C22—H22125.6 (14)
C9—C6—C5109.56 (18)C21—C22—H22113.5 (14)
C9—C6—C7108.78 (17)C24—C23—C22120.2 (3)
C5—C6—C7107.41 (15)C24—C23—H23125.7 (18)
C9—C6—C8107.2 (2)C22—C23—H23114.1 (18)
C5—C6—C8110.80 (16)C23—C24—C25120.2 (3)
C7—C6—C8113.02 (18)C23—C24—H24124 (2)
C7A—C7—C6119.55 (14)C25—C24—H24115 (2)
C7A—C7—H7A108.6 (10)C24—C25—C26119.9 (3)
C6—C7—H7A108.1 (10)C24—C25—H25123 (2)
C7A—C7—H7B105.7 (12)C26—C25—H25116 (2)
C6—C7—H7B105.4 (12)C25—C26—C21120.9 (3)
H7A—C7—H7B109.2 (16)C25—C26—H26122.8 (15)
C7—C7A—C10107.94 (16)C21—C26—H26116.2 (15)
C7—C7A—C1116.03 (17)N1—C27—C21112.26 (14)
C10—C7A—C1107.65 (18)N1—C27—H27A107.6 (10)
C7—C7A—C3A113.88 (14)C21—C27—H27A109.4 (10)
C10—C7A—C3A109.02 (16)N1—C27—H27B109.7 (10)
C1—C7A—C3A101.98 (14)C21—C27—H27B109.3 (9)
C6—C8—H8A106.0 (17)H27A—C27—H27B108.6 (14)
C6—C8—H8B113.3 (12)
O2—S1—N1—C27143.34 (13)C4—C3A—C7A—C741.7 (2)
O1—S1—N1—C2713.02 (15)C3—C3A—C7A—C1075.4 (2)
C11—S1—N1—C27102.79 (13)C4—C3A—C7A—C10162.30 (17)
O2—S1—N1—C442.17 (12)C3—C3A—C7A—C138.26 (18)
O1—S1—N1—C4172.49 (10)C4—C3A—C7A—C184.06 (17)
C11—S1—N1—C471.70 (12)O2—S1—C11—C1614.60 (15)
C7A—C1—C2—C316.1 (2)O1—S1—C11—C16144.48 (13)
C1—C2—C3—C3A8.4 (2)N1—S1—C11—C16100.35 (14)
C2—C3—C3A—C491.4 (2)O2—S1—C11—C12168.15 (13)
C2—C3—C3A—C7A29.3 (2)O1—S1—C11—C1238.27 (15)
C27—N1—C4—C591.02 (18)N1—S1—C11—C1276.90 (14)
S1—N1—C4—C594.50 (15)C16—C11—C12—C131.6 (3)
C27—N1—C4—C3A36.25 (19)S1—C11—C12—C13175.67 (13)
S1—N1—C4—C3A138.22 (12)C11—C12—C13—C140.7 (3)
C3—C3A—C4—N161.53 (19)C12—C13—C14—C150.5 (3)
C7A—C3A—C4—N1177.87 (12)C12—C13—C14—C17178.8 (2)
C3—C3A—C4—C5170.72 (16)C13—C14—C15—C160.7 (3)
C7A—C3A—C4—C554.37 (19)C17—C14—C15—C16178.5 (2)
N1—C4—C5—C6168.18 (13)C14—C15—C16—C110.2 (3)
C3A—C4—C5—C663.9 (2)C12—C11—C16—C151.3 (2)
C4—C5—C6—C9173.61 (18)S1—C11—C16—C15175.91 (13)
C4—C5—C6—C755.6 (2)C26—C21—C22—C230.7 (3)
C4—C5—C6—C868.3 (2)C27—C21—C22—C23178.2 (2)
C9—C6—C7—C7A163.4 (2)C21—C22—C23—C240.2 (4)
C5—C6—C7—C7A44.9 (2)C22—C23—C24—C250.4 (5)
C8—C6—C7—C7A77.6 (2)C23—C24—C25—C260.5 (5)
C6—C7—C7A—C10160.8 (2)C24—C25—C26—C210.0 (4)
C6—C7—C7A—C178.3 (2)C22—C21—C26—C250.6 (3)
C6—C7—C7A—C3A39.6 (3)C27—C21—C26—C25178.4 (2)
C2—C1—C7A—C7157.96 (17)C4—N1—C27—C2170.10 (18)
C2—C1—C7A—C1081.0 (2)S1—N1—C27—C21115.66 (14)
C2—C1—C7A—C3A33.6 (2)C26—C21—C27—N156.0 (2)
C3—C3A—C7A—C7164.04 (17)C22—C21—C27—N1122.83 (18)

Experimental details

Crystal data
Chemical formulaC26H35NO2S
Mr425.61
Crystal system, space groupTriclinic, 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)
V3)1198.48 (6)
Z2
Radiation typeMo Kα
µ (mm1)0.16
Crystal size (mm)0.30 × 0.10 × 0.10
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
13129, 5198, 3347
Rint0.028
(sin θ/λ)max1)0.648
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.123, 1.00
No. of reflections5198
No. of parameters411
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å3)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.

 

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