Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270198017429/ha1248sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270198017429/ha1248Isup2.hkl |
CCDC reference: 142767
Ephedrine (1 g, 6.05 mmol), p-toluenesulfonyl chloride (1.73 g, 9.07 mmol) and tetra-n-butylammonium hydrogen sulfate (0.410 g, 1.21 mmol) in 50 ml of dry benzene was stirred with 10 ml of 50% NaOH at room temperature for 1 h. After completion of the reaction, the organic layer was separated, washed with water and dried over MgSO4. After removal of the solvent, it gave a solid which was recrystallized from methyl alcohol. (yield 80%, m.p. 397–399 K).
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 1997) PLATON (Spek, 1990).
Fig. 1. The structure of title compound showing 50% probability displacement ellipsoids and the atom-numbering scheme. |
C17H21NO3S | F(000) = 340 |
Mr = 319.41 | Dx = 1.294 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2y1 | Cell parameters from 4453 reflections |
a = 6.0272 (2) Å | θ = 2.8–33.1° |
b = 18.6624 (8) Å | µ = 0.21 mm−1 |
c = 7.3642 (3) Å | T = 293 K |
β = 98.148 (1)° | Parallelepiped, colourless |
V = 819.98 (6) Å3 | 0.50 × 0.34 × 0.26 mm |
Z = 2 |
Siemens SMART CCD area detector diffractometer | 3379 independent reflections |
Radiation source: fine-focus sealed tube | 3038 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
Detector resolution: 8.33 pixels mm-1 | θmax = 27.5°, θmin = 2.8° |
ω scans | h = −7→7 |
Absorption correction: empirical (using intensity measurements) SADABS (Sheldrick, 1996) | k = −24→24 |
Tmin = 0.903, Tmax = 0.948 | l = 0→9 |
5485 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.104 | w = 1/[σ2(Fo2) + (0.0586P)2 + 0.0071P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
3379 reflections | Δρmax = 0.40 e Å−3 |
199 parameters | Δρmin = −0.34 e Å−3 |
1 restraint | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.13 (7) |
C17H21NO3S | V = 819.98 (6) Å3 |
Mr = 319.41 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 6.0272 (2) Å | µ = 0.21 mm−1 |
b = 18.6624 (8) Å | T = 293 K |
c = 7.3642 (3) Å | 0.50 × 0.34 × 0.26 mm |
β = 98.148 (1)° |
Siemens SMART CCD area detector diffractometer | 3379 independent reflections |
Absorption correction: empirical (using intensity measurements) SADABS (Sheldrick, 1996) | 3038 reflections with I > 2σ(I) |
Tmin = 0.903, Tmax = 0.948 | Rint = 0.027 |
5485 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.104 | Δρmax = 0.40 e Å−3 |
S = 1.06 | Δρmin = −0.34 e Å−3 |
3379 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
199 parameters | Absolute structure parameter: 0.13 (7) |
1 restraint |
Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0, 88 and 180°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was −35°. Crystal decay was monitored by repeating thirty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible. |
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 | Occ. (<1) | |
S1 | 0.71634 (9) | 0.52841 (3) | 0.16550 (6) | 0.03538 (14) | |
N1 | 0.6812 (3) | 0.53064 (12) | 0.38077 (19) | 0.0332 (3) | |
O1 | 0.5257 (4) | 0.49339 (10) | 0.0678 (2) | 0.0560 (5) | |
O2 | 0.9365 (3) | 0.50049 (10) | 0.1579 (2) | 0.0492 (4) | |
O3 | 1.0979 (3) | 0.50374 (11) | 0.7841 (2) | 0.0617 (6) | |
H3B | 1.0922 | 0.5042 | 0.8947 | 0.093* | |
C1 | 0.7120 (4) | 0.61742 (11) | 0.0817 (3) | 0.0341 (5) | |
C2 | 0.9060 (4) | 0.65819 (14) | 0.1082 (3) | 0.0457 (6) | |
H2A | 1.0395 | 0.6387 | 0.1662 | 0.055* | |
C3 | 0.8984 (6) | 0.72823 (15) | 0.0473 (4) | 0.0578 (7) | |
H3A | 1.0285 | 0.7557 | 0.0650 | 0.069* | |
C4 | 0.7016 (6) | 0.75878 (14) | −0.0397 (3) | 0.0549 (7) | |
C5 | 0.5118 (6) | 0.71686 (16) | −0.0663 (4) | 0.0581 (7) | |
H5A | 0.3791 | 0.7362 | −0.1262 | 0.070* | |
C6 | 0.5137 (5) | 0.64620 (15) | −0.0058 (3) | 0.0463 (6) | |
H6A | 0.3836 | 0.6188 | −0.0238 | 0.056* | |
C7 | 0.6968 (9) | 0.83623 (17) | −0.1010 (5) | 0.0926 (13) | |
H7A | 0.8437 | 0.8566 | −0.0714 | 0.139* | 0.50 |
H7B | 0.5927 | 0.8625 | −0.0393 | 0.139* | 0.50 |
H7C | 0.6510 | 0.8387 | −0.2311 | 0.139* | 0.50 |
H7D | 0.5479 | 0.8486 | −0.1565 | 0.139* | 0.50 |
H7E | 0.7989 | 0.8427 | −0.1885 | 0.139* | 0.50 |
H7F | 0.7406 | 0.8666 | 0.0032 | 0.139* | 0.50 |
C8 | 0.4563 (5) | 0.54798 (18) | 0.4198 (4) | 0.0591 (8) | |
H8A | 0.4552 | 0.5477 | 0.5500 | 0.089* | |
H8B | 0.3519 | 0.5130 | 0.3631 | 0.089* | |
H8C | 0.4141 | 0.5946 | 0.3719 | 0.089* | |
C9 | 0.8738 (4) | 0.54664 (11) | 0.5219 (3) | 0.0337 (5) | |
H9A | 1.0101 | 0.5374 | 0.4673 | 0.040* | |
C10 | 0.8826 (6) | 0.62448 (14) | 0.5843 (4) | 0.0595 (8) | |
H10A | 0.8804 | 0.6553 | 0.4797 | 0.089* | |
H10B | 1.0178 | 0.6326 | 0.6677 | 0.089* | |
H10C | 0.7552 | 0.6347 | 0.6449 | 0.089* | |
C11 | 0.8771 (4) | 0.49567 (13) | 0.6867 (3) | 0.0396 (5) | |
H11A | 0.7686 | 0.5126 | 0.7643 | 0.048* | |
C12 | 0.8253 (4) | 0.41887 (13) | 0.6347 (3) | 0.0387 (5) | |
C13 | 0.6351 (5) | 0.38624 (15) | 0.6823 (4) | 0.0522 (6) | |
H13A | 0.5402 | 0.4118 | 0.7476 | 0.063* | |
C14 | 0.5852 (6) | 0.31557 (16) | 0.6332 (4) | 0.0613 (8) | |
H14A | 0.4587 | 0.2938 | 0.6675 | 0.074* | |
C15 | 0.7223 (6) | 0.27767 (15) | 0.5340 (4) | 0.0630 (8) | |
H15A | 0.6873 | 0.2306 | 0.4994 | 0.076* | |
C16 | 0.9115 (6) | 0.30947 (15) | 0.4861 (4) | 0.0618 (8) | |
H16A | 1.0047 | 0.2836 | 0.4197 | 0.074* | |
C17 | 0.9643 (5) | 0.37935 (15) | 0.5355 (4) | 0.0516 (6) | |
H17B | 1.0930 | 0.4003 | 0.5026 | 0.062* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0435 (3) | 0.0380 (2) | 0.0233 (2) | 0.0017 (3) | 0.00025 (16) | −0.0016 (2) |
N1 | 0.0292 (8) | 0.0437 (8) | 0.0267 (6) | 0.0019 (9) | 0.0037 (6) | 0.0023 (8) |
O1 | 0.0702 (13) | 0.0519 (10) | 0.0397 (8) | −0.0153 (9) | −0.0142 (8) | −0.0032 (7) |
O2 | 0.0612 (12) | 0.0588 (9) | 0.0293 (7) | 0.0238 (9) | 0.0118 (7) | 0.0017 (6) |
O3 | 0.0586 (12) | 0.0873 (14) | 0.0333 (8) | −0.0071 (10) | −0.0142 (7) | −0.0011 (8) |
C1 | 0.0379 (12) | 0.0407 (11) | 0.0237 (9) | 0.0027 (9) | 0.0044 (8) | 0.0045 (8) |
C2 | 0.0404 (14) | 0.0582 (15) | 0.0371 (11) | −0.0044 (11) | 0.0007 (9) | 0.0048 (10) |
C3 | 0.076 (2) | 0.0558 (16) | 0.0424 (13) | −0.0187 (15) | 0.0119 (12) | 0.0002 (11) |
C4 | 0.089 (2) | 0.0414 (13) | 0.0384 (12) | 0.0064 (14) | 0.0223 (13) | 0.0007 (10) |
C5 | 0.0650 (19) | 0.0614 (17) | 0.0484 (14) | 0.0228 (15) | 0.0103 (13) | 0.0140 (12) |
C6 | 0.0402 (13) | 0.0574 (15) | 0.0404 (12) | 0.0045 (11) | 0.0031 (9) | 0.0080 (10) |
C7 | 0.165 (4) | 0.0467 (17) | 0.072 (2) | 0.012 (2) | 0.037 (2) | 0.0089 (15) |
C8 | 0.0387 (14) | 0.086 (2) | 0.0552 (14) | 0.0092 (13) | 0.0138 (11) | 0.0106 (13) |
C9 | 0.0334 (11) | 0.0430 (12) | 0.0252 (9) | −0.0039 (8) | 0.0056 (7) | −0.0026 (7) |
C10 | 0.094 (2) | 0.0464 (14) | 0.0378 (13) | −0.0163 (15) | 0.0085 (14) | −0.0067 (11) |
C11 | 0.0462 (14) | 0.0505 (12) | 0.0220 (8) | −0.0013 (11) | 0.0043 (8) | 0.0009 (9) |
C12 | 0.0461 (14) | 0.0442 (12) | 0.0254 (10) | 0.0048 (10) | 0.0041 (9) | 0.0103 (9) |
C13 | 0.0533 (16) | 0.0621 (16) | 0.0424 (13) | −0.0019 (13) | 0.0113 (11) | 0.0046 (11) |
C14 | 0.065 (2) | 0.0617 (17) | 0.0564 (16) | −0.0144 (14) | 0.0045 (14) | 0.0138 (13) |
C15 | 0.089 (2) | 0.0410 (14) | 0.0569 (16) | −0.0043 (14) | 0.0019 (15) | 0.0045 (12) |
C16 | 0.075 (2) | 0.0485 (15) | 0.0647 (17) | 0.0131 (14) | 0.0193 (15) | 0.0051 (12) |
C17 | 0.0554 (17) | 0.0483 (14) | 0.0532 (14) | 0.0079 (12) | 0.0158 (12) | 0.0073 (11) |
S1—O1 | 1.425 (2) | C7—H7F | 0.9600 |
S1—O2 | 1.434 (2) | C8—H8A | 0.9600 |
S1—N1 | 1.629 (1) | C8—H8B | 0.9600 |
S1—C1 | 1.771 (2) | C8—H8C | 0.9600 |
N1—C8 | 1.461 (3) | C9—C10 | 1.522 (3) |
N1—C9 | 1.475 (3) | C9—C11 | 1.540 (3) |
O3—C11 | 1.427 (3) | C9—H9A | 0.9800 |
O3—H3B | 0.8200 | C10—H10A | 0.9600 |
C1—C6 | 1.383 (3) | C10—H10B | 0.9600 |
C1—C2 | 1.386 (3) | C10—H10C | 0.9600 |
C2—C3 | 1.381 (4) | C11—C12 | 1.505 (3) |
C2—H2A | 0.9300 | C11—H11A | 0.9800 |
C3—C4 | 1.388 (4) | C12—C13 | 1.386 (4) |
C3—H3A | 0.9300 | C12—C17 | 1.398 (3) |
C4—C5 | 1.377 (5) | C13—C14 | 1.389 (4) |
C4—C7 | 1.513 (4) | C13—H13A | 0.9300 |
C5—C6 | 1.391 (4) | C14—C15 | 1.374 (5) |
C5—H5A | 0.9300 | C14—H14A | 0.9300 |
C6—H6A | 0.9300 | C15—C16 | 1.375 (4) |
C7—H7A | 0.9600 | C15—H15A | 0.9300 |
C7—H7B | 0.9600 | C16—C17 | 1.379 (4) |
C7—H7C | 0.9600 | C16—H16A | 0.9300 |
C7—H7D | 0.9600 | C17—H17B | 0.9300 |
C7—H7E | 0.9600 | ||
O1—S1—O2 | 119.9 (1) | H7C—C7—H7F | 141.1 |
O1—S1—N1 | 107.2 (1) | H7D—C7—H7F | 109.5 |
O2—S1—N1 | 107.2 (1) | H7E—C7—H7F | 109.5 |
O1—S1—C1 | 106.4 (1) | N1—C8—H8A | 109.5 |
O2—S1—C1 | 107.2 (1) | N1—C8—H8B | 109.5 |
N1—S1—C1 | 108.5 (1) | H8A—C8—H8B | 109.5 |
C8—N1—C9 | 118.4 (2) | N1—C8—H8C | 109.5 |
C8—N1—S1 | 116.7 (2) | H8A—C8—H8C | 109.5 |
C9—N1—S1 | 119.5 (1) | H8B—C8—H8C | 109.5 |
C11—O3—H3B | 109.5 | N1—C9—C10 | 113.3 (2) |
C6—C1—C2 | 120.6 (2) | N1—C9—C11 | 110.56 (18) |
C6—C1—S1 | 119.72 (18) | C10—C9—C11 | 110.83 (17) |
C2—C1—S1 | 119.69 (17) | N1—C9—H9A | 107.3 |
C3—C2—C1 | 119.1 (2) | C10—C9—H9A | 107.3 |
C3—C2—H2A | 120.5 | C11—C9—H9A | 107.3 |
C1—C2—H2A | 120.5 | C9—C10—H10A | 109.5 |
C2—C3—C4 | 121.7 (3) | C9—C10—H10B | 109.5 |
C2—C3—H3A | 119.1 | H10A—C10—H10B | 109.5 |
C4—C3—H3A | 119.1 | C9—C10—H10C | 109.5 |
C5—C4—C3 | 118.1 (2) | H10A—C10—H10C | 109.5 |
C5—C4—C7 | 121.3 (3) | H10B—C10—H10C | 109.5 |
C3—C4—C7 | 120.6 (3) | O3—C11—C12 | 111.9 (2) |
C4—C5—C6 | 121.6 (3) | O3—C11—C9 | 103.75 (18) |
C4—C5—H5A | 119.2 | C12—C11—C9 | 114.15 (16) |
C6—C5—H5A | 119.2 | O3—C11—H11A | 108.9 |
C1—C6—C5 | 119.0 (3) | C12—C11—H11A | 108.9 |
C1—C6—H6A | 120.5 | C9—C11—H11A | 108.9 |
C5—C6—H6A | 120.5 | C13—C12—C17 | 118.6 (3) |
C4—C7—H7A | 109.5 | C13—C12—C11 | 120.2 (2) |
C4—C7—H7B | 109.5 | C17—C12—C11 | 121.2 (2) |
H7A—C7—H7B | 109.5 | C12—C13—C14 | 120.5 (3) |
C4—C7—H7C | 109.5 | C12—C13—H13A | 119.8 |
H7A—C7—H7C | 109.5 | C14—C13—H13A | 119.8 |
H7B—C7—H7C | 109.5 | C15—C14—C13 | 120.2 (3) |
C4—C7—H7D | 109.5 | C15—C14—H14A | 119.9 |
H7A—C7—H7D | 141.1 | C13—C14—H14A | 119.9 |
H7B—C7—H7D | 56.3 | C14—C15—C16 | 119.8 (3) |
H7C—C7—H7D | 56.3 | C14—C15—H15A | 120.1 |
C4—C7—H7E | 109.5 | C16—C15—H15A | 120.1 |
H7A—C7—H7E | 56.3 | C15—C16—C17 | 120.6 (3) |
H7B—C7—H7E | 141.1 | C15—C16—H16A | 119.7 |
H7C—C7—H7E | 56.3 | C17—C16—H16A | 119.7 |
H7D—C7—H7E | 109.5 | C16—C17—C12 | 120.3 (3) |
C4—C7—H7F | 109.5 | C16—C17—H17B | 119.9 |
H7A—C7—H7F | 56.3 | C12—C17—H17B | 119.9 |
H7B—C7—H7F | 56.3 | ||
O1—S1—N1—C8 | −41.8 (2) | C4—C5—C6—C1 | −0.6 (4) |
O2—S1—N1—C8 | −171.7 (2) | C8—N1—C9—C10 | −54.8 (3) |
C1—S1—N1—C8 | 72.8 (2) | S1—N1—C9—C10 | 98.6 (2) |
O1—S1—N1—C9 | 164.4 (2) | C8—N1—C9—C11 | 70.4 (3) |
O2—S1—N1—C9 | 34.5 (2) | S1—N1—C9—C11 | −136.3 (2) |
C1—S1—N1—C9 | −81.0 (2) | N1—C9—C11—O3 | 164.6 (2) |
O1—S1—C1—C6 | 20.8 (2) | C10—C9—C11—O3 | −68.9 (3) |
O2—S1—C1—C6 | 150.15 (18) | N1—C9—C11—C12 | 42.5 (3) |
N1—S1—C1—C6 | −94.36 (19) | C10—C9—C11—C12 | 169.0 (2) |
O1—S1—C1—C2 | −160.79 (19) | O3—C11—C12—C13 | 126.5 (2) |
O2—S1—C1—C2 | −31.4 (2) | C9—C11—C12—C13 | −116.0 (2) |
N1—S1—C1—C2 | 84.08 (19) | O3—C11—C12—C17 | −54.6 (3) |
C6—C1—C2—C3 | 0.5 (3) | C9—C11—C12—C17 | 62.9 (3) |
S1—C1—C2—C3 | −177.94 (18) | C17—C12—C13—C14 | 0.4 (4) |
C1—C2—C3—C4 | 0.0 (4) | C11—C12—C13—C14 | 179.4 (2) |
C2—C3—C4—C5 | −0.8 (4) | C12—C13—C14—C15 | −1.1 (4) |
C2—C3—C4—C7 | 178.5 (3) | C13—C14—C15—C16 | 1.1 (5) |
C3—C4—C5—C6 | 1.1 (4) | C14—C15—C16—C17 | −0.5 (5) |
C7—C4—C5—C6 | −178.2 (3) | C15—C16—C17—C12 | −0.2 (4) |
C2—C1—C6—C5 | −0.2 (3) | C13—C12—C17—C16 | 0.2 (4) |
S1—C1—C6—C5 | 178.24 (19) | C11—C12—C17—C16 | −178.7 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3B···O2i | 0.82 | 2.27 | 3.047 (2) | 158 |
Symmetry code: (i) x, y, z+1. |
Experimental details
Crystal data | |
Chemical formula | C17H21NO3S |
Mr | 319.41 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 293 |
a, b, c (Å) | 6.0272 (2), 18.6624 (8), 7.3642 (3) |
β (°) | 98.148 (1) |
V (Å3) | 819.98 (6) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.21 |
Crystal size (mm) | 0.50 × 0.34 × 0.26 |
Data collection | |
Diffractometer | Siemens SMART CCD area detector diffractometer |
Absorption correction | Empirical (using intensity measurements) SADABS (Sheldrick, 1996) |
Tmin, Tmax | 0.903, 0.948 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5485, 3379, 3038 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.104, 1.06 |
No. of reflections | 3379 |
No. of parameters | 199 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.40, −0.34 |
Absolute structure | Flack H D (1983), Acta Cryst. A39, 876-881 |
Absolute structure parameter | 0.13 (7) |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXTL (Sheldrick, 1997) PLATON (Spek, 1990).
S1—O1 | 1.425 (2) | N1—C9 | 1.475 (3) |
S1—O2 | 1.434 (2) | O3—C11 | 1.427 (3) |
S1—N1 | 1.629 (1) | C9—C11 | 1.540 (3) |
S1—C1 | 1.771 (2) | C11—C12 | 1.505 (3) |
N1—C8 | 1.461 (3) | ||
O1—S1—O2 | 119.9 (1) | N1—S1—C1 | 108.5 (1) |
O1—S1—N1 | 107.2 (1) | C8—N1—C9 | 118.4 (2) |
O2—S1—N1 | 107.2 (1) | C8—N1—S1 | 116.7 (2) |
O1—S1—C1 | 106.4 (1) | C9—N1—S1 | 119.5 (1) |
O2—S1—C1 | 107.2 (1) | ||
O1—S1—N1—C9 | 164.4 (2) | S1—N1—C9—C10 | 98.6 (2) |
C1—S1—N1—C9 | −81.0 (2) | S1—N1—C9—C11 | −136.3 (2) |
O1—S1—C1—C6 | 20.8 (2) | N1—C9—C11—O3 | 164.6 (2) |
O2—S1—C1—C2 | −31.4 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3B···O2i | 0.82 | 2.27 | 3.047 (2) | 158 |
Symmetry code: (i) x, y, z+1. |
The title compound is an N-tosyl derivative of (-)ephedrine. Generally ephedrine and its derivatives are used as sympathomimetic agents for allergic disorders, central nervous system stimulation, prophylaxis and treatment of hypotension and hypersensitive carotid sinusitis. The structure determination of the title compound, (I), was carried out in order to elucidate the molecular conformation and packing arrangements.
Scheme I
The S atom is in a distorted tetrahedral geometry with the maximum and minimum bond angles around this atom being 119.8 (1) and 106.4 (1)°, respectively. The sum of the bond angles around the N1 atom [354.6 (2)°] indicates the sp2 character of this atom; the deviation of N1 from the S1—C8—C9 plane is 0.206 (2) Å. The S—N, S—O and C—S distances agree with those values reported for the toluenesulfonylamino derivatives (Urtiaga et al., 1994; Arriortua et al., 1995).
The N1—C9—C11—O3, torsion angle [164.6 (2)°] charaterizes the antiperiplanar conformation for the N1 and O3 atoms. The conformation observed across the S1—N1—C9—C11 linkage is -anti-clinal [torsion angle −136.3 (2)°]. The two phenyl ring planes form a dihedral angle of 59.3 (1)° between them (see Fig. 1).
In the solid state, the molecules translated along the c direction are linked through O3—H3B···O2i intermolecular hydrogen bonds (Table 2) to form infinite one-dimensional chains. Along the chain, the phenyl rings are stacked without any π-π interactions.