Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803008092/su6018sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803008092/su6018Isup2.hkl |
CCDC reference: 214635
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.005 Å
- R factor = 0.045
- wR factor = 0.091
- Data-to-parameter ratio = 18.3
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level A:
TYPE_089 Alert A _refine_ls_abs_structure_Flack is not of type numb.
Alert Level C:
GOODF_01 Alert C The least squares goodness of fit parameter lies outside the range 0.80 <> 2.00 Goodness of fit given = 0.799 PLAT_420 Alert C D-H Without Acceptor N(1) - H(1B) ? General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 27.53 From the CIF: _reflns_number_total 4879 Count of symmetry unique reflns 2808 Completeness (_total/calc) 173.75% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2071 Fraction of Friedel pairs measured 0.738 Are heavy atom types Z>Si present yes Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.
1 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check
A mixture of (R,S)- and (S,S)-2-amino-3-methyl-1-(6-methoxy-2-naphthyl)butan-1-ol were prepared as described in the literature (Reetz et al., 1987), and were used without separation (the ratio of R,S to S,S is about 87 to 13 estimated by 1H NMR analysis). Toluenesulfonyl chloride (0.63 g, 3.3 mmol) and triethylamine (5.0 mmol) were added to the solution of 0.78 g (3.0 mmol) of the amino alcohol in 50 ml of tetrahydrafuran. The mixture was stirred at 273 K for 2 h and then left at room temperature overnight. Water (30 ml) was then added and the organic layers separated. The aqueous layer was extracted with ethyl acetate (3 × 25 ml). The combined organic phase was washed with brine, dried over Na2SO4 and the solvents were removed under reduced pressure. The crude products were purified by flash chromatography and crystallized from dichloromethane and hexane to afford the title compound (0.87 g, 71%).
The absolute configuration of the molecule indicates that atom C1 has an S configuration and atom C2 an R configuration. The Flack (1983) parameter is 0.03 (9). The C-bound H atoms were placed in their geometrically calculated positions and included in the final refinement in the riding-model approximation.
Data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SHELXTL-NT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-NT; software used to prepare material for publication: SHELXTL-NT.
Fig. 1. Molecular structure of (I), with displacement ellipsoids at the 30% probability level. | |
Fig. 2. Crystal packing viewed down the b axis; dashed lines indicate hydrogen bonding. |
C23H27NO4S | Dx = 1.293 Mg m−3 |
Mr = 413.52 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 3575 reflections |
a = 7.3107 (13) Å | θ = 1–27.5° |
b = 11.5702 (19) Å | µ = 0.18 mm−1 |
c = 25.117 (4) Å | T = 294 K |
V = 2124.6 (6) Å3 | Prism, colourless |
Z = 4 | 0.32 × 0.28 × 0.24 mm |
F(000) = 880 |
Bruker CCD area-detector diffractometer | 4879 independent reflections |
Radiation source: fine-focus sealed tube | 2113 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.072 |
ϕ and ω scans | θmax = 27.5°, θmin = 3.2° |
Absorption correction: multi-scan (SADABS; Sheldrick 1996) | h = −9→9 |
Tmin = 0.944, Tmax = 0.958 | k = −14→13 |
14469 measured reflections | l = −23→32 |
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)] = 0.045 | H-atom parameters constrained |
wR(F2) = 0.091 | w = 1/[σ2(Fo2) + (0.03P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.80 | (Δ/σ)max = 0.001 |
4879 reflections | Δρmax = 0.25 e Å−3 |
266 parameters | Δρmin = −0.20 e Å−3 |
3 restraints | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.03 (9), 0000 Friedel pairs |
C23H27NO4S | V = 2124.6 (6) Å3 |
Mr = 413.52 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 7.3107 (13) Å | µ = 0.18 mm−1 |
b = 11.5702 (19) Å | T = 294 K |
c = 25.117 (4) Å | 0.32 × 0.28 × 0.24 mm |
Bruker CCD area-detector diffractometer | 4879 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick 1996) | 2113 reflections with I > 2σ(I) |
Tmin = 0.944, Tmax = 0.958 | Rint = 0.072 |
14469 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | H-atom parameters constrained |
wR(F2) = 0.091 | Δρmax = 0.25 e Å−3 |
S = 0.80 | Δρmin = −0.20 e Å−3 |
4879 reflections | Absolute structure: Flack (1983) |
266 parameters | Absolute structure parameter: 0.03 (9), 0000 Friedel pairs |
3 restraints |
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 | 0.89213 (11) | 0.55394 (7) | 0.78967 (3) | 0.0473 (2) | |
O1 | 0.3267 (3) | 0.78719 (18) | 0.76802 (7) | 0.0675 (7) | |
H1A | 0.2157 | 0.7811 | 0.7718 | 0.101* | |
O2 | 0.4350 (4) | 0.5250 (2) | 1.08884 (9) | 0.0861 (8) | |
O3 | 0.9870 (3) | 0.46719 (19) | 0.75994 (7) | 0.0632 (6) | |
O4 | 0.9685 (3) | 0.66785 (16) | 0.79438 (8) | 0.0566 (6) | |
N1 | 0.6906 (3) | 0.5672 (2) | 0.76437 (9) | 0.0479 (7) | |
H1B | 0.6325 | 0.5047 | 0.7567 | 0.057* | |
C1 | 0.5976 (4) | 0.6775 (2) | 0.75330 (10) | 0.0445 (8) | |
H1C | 0.6732 | 0.7397 | 0.7681 | 0.053* | |
C2 | 0.4131 (4) | 0.6802 (2) | 0.78197 (10) | 0.0460 (8) | |
H2A | 0.3377 | 0.6160 | 0.7690 | 0.055* | |
C3 | 0.4319 (4) | 0.6707 (3) | 0.84175 (12) | 0.0472 (8) | |
C4 | 0.3694 (4) | 0.5770 (3) | 0.86830 (13) | 0.0583 (9) | |
H4B | 0.3144 | 0.5174 | 0.8494 | 0.070* | |
C5 | 0.3861 (5) | 0.5677 (3) | 0.92531 (13) | 0.0513 (8) | |
C6 | 0.3222 (5) | 0.4720 (3) | 0.95269 (16) | 0.0779 (11) | |
H6A | 0.2658 | 0.4123 | 0.9341 | 0.094* | |
C7 | 0.3411 (5) | 0.4646 (4) | 1.00643 (15) | 0.0813 (12) | |
H7A | 0.2962 | 0.3999 | 1.0241 | 0.098* | |
C8 | 0.4258 (5) | 0.5514 (4) | 1.03559 (14) | 0.0675 (10) | |
C9 | 0.4884 (5) | 0.6479 (3) | 1.01131 (13) | 0.0631 (10) | |
H9 | 0.5449 | 0.7060 | 1.0309 | 0.076* | |
C10 | 0.4656 (4) | 0.6590 (3) | 0.95387 (14) | 0.0556 (9) | |
C11 | 0.5270 (5) | 0.7561 (3) | 0.92686 (14) | 0.0656 (10) | |
H11A | 0.5796 | 0.8171 | 0.9455 | 0.079* | |
C12 | 0.5096 (4) | 0.7619 (3) | 0.87195 (13) | 0.0607 (9) | |
H12A | 0.5501 | 0.8278 | 0.8543 | 0.073* | |
C13 | 0.5269 (7) | 0.6015 (3) | 1.12179 (14) | 0.1056 (17) | |
H13A | 0.5206 | 0.5745 | 1.1579 | 0.158* | |
H13B | 0.4712 | 0.6764 | 1.1194 | 0.158* | |
H13C | 0.6526 | 0.6065 | 1.1110 | 0.158* | |
C14 | 0.5815 (5) | 0.6977 (3) | 0.69304 (10) | 0.0534 (9) | |
H14A | 0.5159 | 0.7708 | 0.6880 | 0.064* | |
C15 | 0.7690 (5) | 0.7120 (3) | 0.66811 (12) | 0.0781 (11) | |
H15A | 0.7557 | 0.7300 | 0.6310 | 0.117* | |
H15B | 0.8369 | 0.6414 | 0.6719 | 0.117* | |
H15C | 0.8331 | 0.7736 | 0.6856 | 0.117* | |
C16 | 0.4717 (5) | 0.6043 (3) | 0.66478 (12) | 0.0874 (13) | |
H16A | 0.4553 | 0.6254 | 0.6281 | 0.131* | |
H16B | 0.3544 | 0.5965 | 0.6816 | 0.131* | |
H16C | 0.5362 | 0.5322 | 0.6668 | 0.131* | |
C17 | 0.8640 (4) | 0.4988 (3) | 0.85464 (11) | 0.0394 (8) | |
C18 | 0.8247 (5) | 0.3843 (3) | 0.86198 (12) | 0.0614 (10) | |
H18A | 0.8102 | 0.3356 | 0.8328 | 0.074* | |
C19 | 0.8067 (5) | 0.3418 (3) | 0.91305 (13) | 0.0677 (11) | |
H19A | 0.7769 | 0.2643 | 0.9177 | 0.081* | |
C20 | 0.8311 (4) | 0.4092 (3) | 0.95679 (13) | 0.0540 (9) | |
C21 | 0.8687 (5) | 0.5237 (3) | 0.94852 (13) | 0.0625 (10) | |
H21A | 0.8838 | 0.5722 | 0.9777 | 0.075* | |
C22 | 0.8848 (4) | 0.5685 (3) | 0.89785 (12) | 0.0552 (9) | |
H22A | 0.9098 | 0.6467 | 0.8932 | 0.066* | |
C23 | 0.8160 (5) | 0.3623 (3) | 1.01318 (12) | 0.0842 (13) | |
H23A | 0.6947 | 0.3331 | 1.0190 | 0.126* | |
H23B | 0.8408 | 0.4231 | 1.0382 | 0.126* | |
H23C | 0.9030 | 0.3010 | 1.0180 | 0.126* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0406 (4) | 0.0590 (5) | 0.0423 (5) | 0.0019 (5) | −0.0014 (4) | 0.0046 (5) |
O1 | 0.0515 (15) | 0.0932 (15) | 0.0579 (15) | 0.0182 (13) | 0.0012 (11) | 0.0155 (13) |
O2 | 0.122 (2) | 0.0950 (18) | 0.0408 (15) | 0.0049 (17) | −0.0030 (14) | 0.0088 (14) |
O3 | 0.0618 (15) | 0.0799 (14) | 0.0479 (13) | 0.0201 (14) | 0.0084 (11) | 0.0000 (13) |
O4 | 0.0446 (13) | 0.0607 (14) | 0.0645 (14) | −0.0144 (11) | −0.0059 (11) | 0.0122 (13) |
N1 | 0.0459 (16) | 0.0485 (14) | 0.0493 (15) | −0.0073 (14) | −0.0116 (12) | 0.0092 (13) |
C1 | 0.043 (2) | 0.0506 (19) | 0.0394 (17) | 0.0005 (17) | −0.0011 (17) | 0.0047 (16) |
C2 | 0.043 (2) | 0.0560 (19) | 0.0387 (19) | 0.0025 (16) | −0.0056 (17) | 0.0106 (16) |
C3 | 0.033 (2) | 0.057 (2) | 0.052 (2) | 0.0027 (16) | 0.0004 (16) | 0.0104 (19) |
C4 | 0.045 (2) | 0.078 (2) | 0.052 (2) | −0.008 (2) | −0.0020 (18) | 0.006 (2) |
C5 | 0.0444 (19) | 0.056 (2) | 0.054 (2) | −0.003 (2) | 0.0041 (19) | 0.002 (2) |
C6 | 0.084 (3) | 0.079 (3) | 0.071 (3) | −0.008 (2) | −0.001 (2) | 0.004 (3) |
C7 | 0.097 (3) | 0.091 (3) | 0.055 (3) | 0.002 (3) | 0.001 (2) | 0.014 (3) |
C8 | 0.073 (3) | 0.086 (3) | 0.044 (2) | 0.019 (2) | 0.009 (2) | 0.006 (2) |
C9 | 0.068 (3) | 0.077 (3) | 0.044 (2) | 0.009 (2) | 0.0023 (19) | −0.002 (2) |
C10 | 0.046 (2) | 0.056 (2) | 0.065 (2) | 0.0109 (18) | 0.0086 (19) | 0.014 (2) |
C11 | 0.068 (3) | 0.057 (2) | 0.072 (3) | −0.001 (2) | −0.003 (2) | −0.004 (2) |
C12 | 0.061 (2) | 0.071 (2) | 0.050 (2) | 0.011 (2) | −0.0022 (19) | 0.014 (2) |
C13 | 0.176 (5) | 0.087 (3) | 0.054 (2) | 0.018 (3) | −0.028 (3) | −0.014 (2) |
C14 | 0.057 (2) | 0.068 (2) | 0.0348 (17) | 0.0081 (19) | −0.0011 (17) | 0.0113 (16) |
C15 | 0.085 (3) | 0.098 (3) | 0.051 (2) | 0.003 (2) | 0.022 (2) | 0.016 (2) |
C16 | 0.101 (3) | 0.112 (3) | 0.049 (2) | −0.004 (3) | −0.025 (2) | 0.003 (2) |
C17 | 0.0369 (19) | 0.0443 (17) | 0.0370 (19) | 0.0016 (16) | −0.0064 (15) | −0.0008 (15) |
C18 | 0.088 (3) | 0.064 (2) | 0.033 (2) | −0.013 (2) | −0.0095 (18) | −0.0055 (18) |
C19 | 0.104 (3) | 0.053 (2) | 0.047 (2) | −0.015 (2) | −0.006 (2) | 0.005 (2) |
C20 | 0.058 (3) | 0.067 (2) | 0.0376 (19) | 0.0110 (18) | −0.0045 (17) | 0.0065 (19) |
C21 | 0.085 (3) | 0.062 (2) | 0.040 (2) | 0.007 (2) | −0.012 (2) | −0.0088 (18) |
C22 | 0.068 (2) | 0.0515 (19) | 0.046 (2) | 0.004 (2) | −0.003 (2) | 0.0016 (18) |
C23 | 0.109 (4) | 0.090 (3) | 0.054 (2) | 0.012 (3) | −0.010 (2) | 0.017 (2) |
S1—O3 | 1.430 (2) | C11—C12 | 1.387 (4) |
S1—O4 | 1.4365 (19) | C11—H11A | 0.9300 |
S1—N1 | 1.612 (2) | C12—H12A | 0.9300 |
S1—C17 | 1.764 (3) | C13—H13A | 0.9600 |
O1—C2 | 1.434 (3) | C13—H13B | 0.9600 |
O1—H1A | 0.8200 | C13—H13C | 0.9600 |
O2—C8 | 1.373 (4) | C14—C15 | 1.516 (4) |
O2—C13 | 1.386 (4) | C14—C16 | 1.521 (4) |
N1—C1 | 1.472 (3) | C14—H14A | 0.9800 |
N1—H1B | 0.8600 | C15—H15A | 0.9600 |
C1—C2 | 1.529 (4) | C15—H15B | 0.9600 |
C1—C14 | 1.536 (4) | C15—H15C | 0.9600 |
C1—H1C | 0.9800 | C16—H16A | 0.9600 |
C2—C3 | 1.512 (4) | C16—H16B | 0.9600 |
C2—H2A | 0.9800 | C16—H16C | 0.9600 |
C3—C4 | 1.352 (4) | C17—C22 | 1.360 (3) |
C3—C12 | 1.419 (4) | C17—C18 | 1.369 (3) |
C4—C5 | 1.441 (4) | C18—C19 | 1.380 (4) |
C4—H4B | 0.9300 | C18—H18A | 0.9300 |
C5—C6 | 1.385 (4) | C19—C20 | 1.359 (4) |
C5—C10 | 1.403 (4) | C19—H19A | 0.9300 |
C6—C7 | 1.359 (4) | C20—C21 | 1.369 (4) |
C6—H6A | 0.9300 | C20—C23 | 1.521 (4) |
C7—C8 | 1.388 (5) | C21—C22 | 1.379 (4) |
C7—H7A | 0.9300 | C21—H21A | 0.9300 |
C8—C9 | 1.352 (4) | C22—H22A | 0.9300 |
C9—C10 | 1.458 (4) | C23—H23A | 0.9600 |
C9—H9 | 0.9300 | C23—H23B | 0.9600 |
C10—C11 | 1.387 (4) | C23—H23C | 0.9600 |
O3—S1—O4 | 119.88 (13) | C11—C12—H12A | 118.9 |
O3—S1—N1 | 107.74 (13) | C3—C12—H12A | 118.9 |
O4—S1—N1 | 107.49 (12) | O2—C13—H13A | 109.5 |
O3—S1—C17 | 106.60 (13) | O2—C13—H13B | 109.5 |
O4—S1—C17 | 107.49 (14) | H13A—C13—H13B | 109.5 |
N1—S1—C17 | 107.02 (13) | O2—C13—H13C | 109.5 |
C2—O1—H1A | 109.5 | H13A—C13—H13C | 109.5 |
C8—O2—C13 | 117.6 (3) | H13B—C13—H13C | 109.5 |
C1—N1—S1 | 125.38 (19) | C15—C14—C16 | 111.2 (3) |
C1—N1—H1B | 117.3 | C15—C14—C1 | 110.7 (3) |
S1—N1—H1B | 117.3 | C16—C14—C1 | 113.1 (3) |
N1—C1—C2 | 109.6 (2) | C15—C14—H14A | 107.2 |
N1—C1—C14 | 110.7 (2) | C16—C14—H14A | 107.2 |
C2—C1—C14 | 113.2 (2) | C1—C14—H14A | 107.2 |
N1—C1—H1C | 107.7 | C14—C15—H15A | 109.5 |
C2—C1—H1C | 107.7 | C14—C15—H15B | 109.5 |
C14—C1—H1C | 107.7 | H15A—C15—H15B | 109.5 |
O1—C2—C3 | 110.2 (2) | C14—C15—H15C | 109.5 |
O1—C2—C1 | 106.9 (2) | H15A—C15—H15C | 109.5 |
C3—C2—C1 | 112.7 (2) | H15B—C15—H15C | 109.5 |
O1—C2—H2A | 109.0 | C14—C16—H16A | 109.5 |
C3—C2—H2A | 109.0 | C14—C16—H16B | 109.5 |
C1—C2—H2A | 109.0 | H16A—C16—H16B | 109.5 |
C4—C3—C12 | 117.9 (3) | C14—C16—H16C | 109.5 |
C4—C3—C2 | 121.2 (3) | H16A—C16—H16C | 109.5 |
C12—C3—C2 | 120.9 (3) | H16B—C16—H16C | 109.5 |
C3—C4—C5 | 121.4 (3) | C22—C17—C18 | 119.3 (3) |
C3—C4—H4B | 119.3 | C22—C17—S1 | 120.7 (2) |
C5—C4—H4B | 119.3 | C18—C17—S1 | 119.9 (2) |
C6—C5—C10 | 119.2 (3) | C17—C18—C19 | 119.3 (3) |
C6—C5—C4 | 121.7 (3) | C17—C18—H18A | 120.3 |
C10—C5—C4 | 119.1 (3) | C19—C18—H18A | 120.3 |
C7—C6—C5 | 120.6 (4) | C20—C19—C18 | 122.3 (3) |
C7—C6—H6A | 119.7 | C20—C19—H19A | 118.8 |
C5—C6—H6A | 119.7 | C18—C19—H19A | 118.8 |
C6—C7—C8 | 121.6 (4) | C19—C20—C21 | 117.3 (3) |
C6—C7—H7A | 119.2 | C19—C20—C23 | 122.6 (3) |
C8—C7—H7A | 119.2 | C21—C20—C23 | 120.1 (3) |
C9—C8—O2 | 127.3 (4) | C20—C21—C22 | 121.4 (3) |
C9—C8—C7 | 120.7 (3) | C20—C21—H21A | 119.3 |
O2—C8—C7 | 112.0 (4) | C22—C21—H21A | 119.3 |
C8—C9—C10 | 118.7 (3) | C17—C22—C21 | 120.2 (3) |
C8—C9—H9 | 120.6 | C17—C22—H22A | 119.9 |
C10—C9—H9 | 120.6 | C21—C22—H22A | 119.9 |
C11—C10—C5 | 119.6 (3) | C20—C23—H23A | 109.5 |
C11—C10—C9 | 121.2 (3) | C20—C23—H23B | 109.5 |
C5—C10—C9 | 119.1 (3) | H23A—C23—H23B | 109.5 |
C10—C11—C12 | 119.7 (3) | C20—C23—H23C | 109.5 |
C10—C11—H11A | 120.1 | H23A—C23—H23C | 109.5 |
C12—C11—H11A | 120.1 | H23B—C23—H23C | 109.5 |
C11—C12—C3 | 122.1 (3) | ||
O3—S1—N1—C1 | −135.8 (2) | C4—C5—C10—C9 | −177.9 (3) |
O4—S1—N1—C1 | −5.4 (3) | C8—C9—C10—C11 | 179.9 (3) |
C17—S1—N1—C1 | 109.8 (2) | C8—C9—C10—C5 | −2.4 (5) |
S1—N1—C1—C2 | −123.9 (2) | C5—C10—C11—C12 | −0.1 (5) |
S1—N1—C1—C14 | 110.6 (3) | C9—C10—C11—C12 | 177.5 (3) |
N1—C1—C2—O1 | −177.8 (2) | C10—C11—C12—C3 | −0.6 (5) |
C14—C1—C2—O1 | −53.7 (3) | C4—C3—C12—C11 | 1.8 (5) |
N1—C1—C2—C3 | 60.9 (3) | C2—C3—C12—C11 | 179.4 (3) |
C14—C1—C2—C3 | −175.0 (2) | N1—C1—C14—C15 | −65.0 (3) |
O1—C2—C3—C4 | 127.1 (3) | C2—C1—C14—C15 | 171.5 (3) |
C1—C2—C3—C4 | −113.5 (3) | N1—C1—C14—C16 | 60.6 (4) |
O1—C2—C3—C12 | −50.4 (4) | C2—C1—C14—C16 | −62.9 (4) |
C1—C2—C3—C12 | 69.0 (3) | O3—S1—C17—C22 | 140.1 (3) |
C12—C3—C4—C5 | −2.1 (5) | O4—S1—C17—C22 | 10.4 (3) |
C2—C3—C4—C5 | −179.7 (3) | N1—S1—C17—C22 | −104.8 (3) |
C3—C4—C5—C6 | 180.0 (3) | O3—S1—C17—C18 | −38.5 (3) |
C3—C4—C5—C10 | 1.4 (5) | O4—S1—C17—C18 | −168.2 (3) |
C10—C5—C6—C7 | −2.0 (5) | N1—S1—C17—C18 | 76.5 (3) |
C4—C5—C6—C7 | 179.4 (3) | C22—C17—C18—C19 | 0.0 (5) |
C5—C6—C7—C8 | −0.6 (6) | S1—C17—C18—C19 | 178.7 (3) |
C13—O2—C8—C9 | −3.8 (5) | C17—C18—C19—C20 | −1.6 (6) |
C13—O2—C8—C7 | 176.0 (3) | C18—C19—C20—C21 | 2.2 (5) |
C6—C7—C8—C9 | 1.7 (6) | C18—C19—C20—C23 | −178.5 (3) |
C6—C7—C8—O2 | −178.2 (3) | C19—C20—C21—C22 | −1.2 (5) |
O2—C8—C9—C10 | 179.7 (3) | C23—C20—C21—C22 | 179.4 (3) |
C7—C8—C9—C10 | −0.1 (5) | C18—C17—C22—C21 | 0.9 (5) |
C6—C5—C10—C11 | −178.8 (3) | S1—C17—C22—C21 | −177.8 (3) |
C4—C5—C10—C11 | −0.2 (5) | C20—C21—C22—C17 | −0.3 (5) |
C6—C5—C10—C9 | 3.5 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1B···O1i | 0.86 | 2.61 | 3.343 (3) | 144 |
O1—H1A···O4ii | 0.82 | 2.30 | 3.033 (3) | 149 |
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C23H27NO4S |
Mr | 413.52 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 294 |
a, b, c (Å) | 7.3107 (13), 11.5702 (19), 25.117 (4) |
V (Å3) | 2124.6 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.18 |
Crystal size (mm) | 0.32 × 0.28 × 0.24 |
Data collection | |
Diffractometer | Bruker CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick 1996) |
Tmin, Tmax | 0.944, 0.958 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14469, 4879, 2113 |
Rint | 0.072 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.091, 0.80 |
No. of reflections | 4879 |
No. of parameters | 266 |
No. of restraints | 3 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.25, −0.20 |
Absolute structure | Flack (1983) |
Absolute structure parameter | 0.03 (9), 0000 Friedel pairs |
Computer programs: SMART (Siemens, 1995), SMART, SHELXTL-NT (Siemens, 1995), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL-NT.
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1B···O1i | 0.86 | 2.61 | 3.343 (3) | 144 |
O1—H1A···O4ii | 0.82 | 2.30 | 3.033 (3) | 149 |
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) x−1, y, z. |
Chiral amino alcohols and their sulfonamides are important ligands in asymmetric synthesis (Itsuno et al., 1885; Corey et al., 1987, 1998; Deloux et al., 1993; Ager et al., 1996; Otsuka et al., 1995; Hu et al., 2001). In some instances, the ligands with two stereo centres usually give better enantioselectivity than ligands with one stereocentre (You et al., 2000, 2001). Recently, we have prepared a series of amino alcohols with two stereocentres using L-valine as the starting material and found that the groups adjacent to the new chiral centres have strongly influenced the enatioselectivity of the reaction (Li et al., 2003). Here we report the preparation and crystal structure of the new chiral sulfonamide (1R,2S)-1-(6-methoxy-2-naphthyl)-3-methyl-2-(p-methylphenylsulfonylamino)- 1-(6-methoxy-2-naphthyl)butan-1-ol, (I).
Fig. 1 shows the structure of compound (I), which is U-shaped with the phenyl and naphthalene rings almost parallel. An intramolecular π-π contact is observed between a ring of the naphthaline group (atoms C3, C4, C5, C10, C11 and C12) and the phenyl ring (atoms C5, C6, C7, C8, C9 and C10). These rings are inclined to one another by an angle of 14.6 (2)°, and the ring centroids are separated by a distance of 3.81 (5) Å. A weak C—H···π contact in C23—H23A···CgB (CgB is the centroid of plane through atoms C5, C6, C7, C8, C9 and C10) is also found, with a distance of 3.49 (5) Å.
In the crystal structure, there are two hydrogen bonds present. One involves the hydroxyl and a sulfonamide O-atom [O1—H1A···O4ii with a D···A distances of 3.033 (3) Å and angle of 149°], and the other involves the amine and the hydroxyl group, N1—H1···O1i, with a D···A distance of 3.343 Å and an angle of 143.9° (see Table 2 for symmetry codes). A hydrogen-bonded polymer chain is formed with the molecules stacking up the a axis (Fig. 2).