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organic compounds
(+)-N-[2-(4-Chlorophenyl)propanoyl]bornane-10,2-sultam
aKey Laboratory of Pesticides and Chemical Biology, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China
*Correspondence e-mail: chshliu@mail.ccnu.edu.cn
In the molecular structure of the title compound, C19H24ClNO3S, the six-membered ring of the bornane unit shows a boat form, while the five-membered ring of the sultam unit adopts a Intramolecular C—H⋯N and C—H⋯O interactions are observed. In the molecules are connected by intermolecular C—H⋯O hydrogen bonds into a chain running along the b axis. The crystal was a partial with a twin ratio of 0.73 (1):0.27 (1).
Experimental
Crystal data
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Data collection
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Data collection: SMART (Bruker, 2001); cell SAINT-Plus (Bruker, 2001
); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997
); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997
); molecular graphics: SHELXTL (Bruker, 2001
); software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536807067980/is2250sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536807067980/is2250Isup2.hkl
For the preparation of compound (I), 2.4 ml n-BuLi (hexane, 2.5 mol/L) was added over 30 min to the THF (25 ml) solution of (+)-N-[2-(4-chlorophenyl)-ethanoyl]bornane-10,2-sultam (1.84 g, 5 mmol) at 193 K. After stirring the mixture at 193 K for 1 h, iodomethane 1.6 ml in 4.5 ml HMPA was added and then stirred at 193 K for 3 h. The solution was slowly warming up to room temperature, quenched with water and extracted bt Et2O to afford a crude product. Single crystals appropriate for data collection were obtained by slow evaporation of a dichloromethane solution at 293 K.
All H atoms were constrained to an ideal geometry (C—H = 0.93 - 0.98 Å) and Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C). The ratio of the twin components (major to minor) in crystal selected for diffraction is 0.73 (1):0.27 (1). The
of the sultam unit is consistent with the known of (+)-2,10-sultam (Boiadjiev & Lightner, 2001). The major component is (+)-N-[(2S)-(4-chlorophenyl)-propanoyl] bornane-10,2-sultam, and the minor is (+)-N-[(2R)-(4-chlorophenyl)-propanoyl] bornane-10,2-sultam. The result was confirmed by HPLC.Data collection: SMART (Bruker, 2001); cell
SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL (Bruker, 2001).C19H24ClNO3S | F(000) = 808 |
Mr = 381.90 | Dx = 1.337 Mg m−3 |
Monoclinic, C2 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C 2y | Cell parameters from 2555 reflections |
a = 21.0863 (16) Å | θ = 2.8–26.0° |
b = 7.7948 (6) Å | µ = 0.33 mm−1 |
c = 12.102 (1) Å | T = 295 K |
β = 107.433 (1)° | Block, colorless |
V = 1897.8 (3) Å3 | 0.30 × 0.20 × 0.20 mm |
Z = 4 |
Bruker SMART APEX CCD area-detector diffractometer | 3146 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.032 |
Graphite monochromator | θmax = 27.0°, θmin = 1.8° |
ϕ and ω scans | h = −25→26 |
5780 measured reflections | k = −9→9 |
3715 independent reflections | l = −14→15 |
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)] = 0.052 | H-atom parameters constrained |
wR(F2) = 0.180 | w = 1/[σ2(Fo2) + (0.1128P)2 + 0.2113P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max = 0.001 |
3715 reflections | Δρmax = 0.34 e Å−3 |
229 parameters | Δρmin = −0.22 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 1503 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.27 (1) |
C19H24ClNO3S | V = 1897.8 (3) Å3 |
Mr = 381.90 | Z = 4 |
Monoclinic, C2 | Mo Kα radiation |
a = 21.0863 (16) Å | µ = 0.33 mm−1 |
b = 7.7948 (6) Å | T = 295 K |
c = 12.102 (1) Å | 0.30 × 0.20 × 0.20 mm |
β = 107.433 (1)° |
Bruker SMART APEX CCD area-detector diffractometer | 3146 reflections with I > 2σ(I) |
5780 measured reflections | Rint = 0.032 |
3715 independent reflections |
R[F2 > 2σ(F2)] = 0.052 | H-atom parameters constrained |
wR(F2) = 0.180 | Δρmax = 0.34 e Å−3 |
S = 1.10 | Δρmin = −0.22 e Å−3 |
3715 reflections | Absolute structure: Flack (1983), 1503 Friedel pairs |
229 parameters | Absolute structure parameter: 0.27 (1) |
1 restraint |
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 | ||
C1 | 0.41765 (17) | 0.1484 (5) | 0.2515 (3) | 0.0363 (8) | |
H1 | 0.4074 | 0.1971 | 0.3188 | 0.044* | |
C2 | 0.3700 (2) | 0.2236 (6) | 0.1388 (4) | 0.0492 (10) | |
H2A | 0.3436 | 0.3165 | 0.1552 | 0.059* | |
H2B | 0.3942 | 0.2647 | 0.0873 | 0.059* | |
C3 | 0.32641 (19) | 0.0678 (7) | 0.0869 (4) | 0.0501 (10) | |
H3 | 0.3002 | 0.0816 | 0.0056 | 0.060* | |
C4 | 0.28491 (19) | 0.0218 (7) | 0.1686 (4) | 0.0568 (12) | |
H4A | 0.2497 | −0.0582 | 0.1318 | 0.068* | |
H4B | 0.2655 | 0.1236 | 0.1913 | 0.068* | |
C5 | 0.33625 (18) | −0.0616 (6) | 0.2743 (4) | 0.0463 (10) | |
H5A | 0.3387 | −0.0004 | 0.3453 | 0.056* | |
H5B | 0.3256 | −0.1810 | 0.2829 | 0.056* | |
C6 | 0.40133 (17) | −0.0439 (5) | 0.2421 (3) | 0.0364 (8) | |
C7 | 0.37733 (19) | −0.0803 (6) | 0.1092 (3) | 0.0486 (10) | |
C8 | 0.4297 (2) | −0.0585 (7) | 0.0450 (4) | 0.0582 (13) | |
H8A | 0.4640 | −0.1429 | 0.0721 | 0.087* | |
H8B | 0.4488 | 0.0542 | 0.0595 | 0.087* | |
H8C | 0.4090 | −0.0731 | −0.0367 | 0.087* | |
C9 | 0.3474 (3) | −0.2582 (7) | 0.0795 (5) | 0.0661 (14) | |
H9A | 0.3291 | −0.2688 | −0.0030 | 0.099* | |
H9B | 0.3128 | −0.2747 | 0.1150 | 0.099* | |
H9C | 0.3813 | −0.3433 | 0.1076 | 0.099* | |
C10 | 0.46138 (18) | −0.1414 (5) | 0.3168 (4) | 0.0421 (9) | |
H10A | 0.4653 | −0.2514 | 0.2819 | 0.051* | |
H10B | 0.4570 | −0.1614 | 0.3933 | 0.051* | |
C11 | 0.5168 (2) | 0.3268 (5) | 0.2714 (4) | 0.0438 (9) | |
C12 | 0.59037 (19) | 0.3421 (6) | 0.2804 (4) | 0.0511 (11) | |
H12 | 0.6053 | 0.2315 | 0.2587 | 0.061* | |
C13 | 0.5985 (3) | 0.4787 (9) | 0.1933 (5) | 0.0770 (15) | |
H13A | 0.5714 | 0.4486 | 0.1168 | 0.115* | |
H13B | 0.6443 | 0.4837 | 0.1947 | 0.115* | |
H13C | 0.5851 | 0.5886 | 0.2142 | 0.115* | |
C14 | 0.63302 (19) | 0.3854 (6) | 0.4024 (4) | 0.0475 (10) | |
C15 | 0.7005 (2) | 0.3585 (7) | 0.4306 (5) | 0.0612 (13) | |
H15 | 0.7185 | 0.3183 | 0.3741 | 0.073* | |
C16 | 0.7427 (2) | 0.3902 (9) | 0.5418 (5) | 0.0722 (16) | |
H16 | 0.7879 | 0.3674 | 0.5602 | 0.087* | |
C17 | 0.7166 (2) | 0.4547 (6) | 0.6224 (4) | 0.0513 (11) | |
C18 | 0.6501 (2) | 0.4816 (7) | 0.5981 (4) | 0.0541 (10) | |
H18 | 0.6327 | 0.5210 | 0.6555 | 0.065* | |
C19 | 0.6085 (2) | 0.4500 (6) | 0.4877 (4) | 0.0525 (11) | |
H19 | 0.5633 | 0.4726 | 0.4706 | 0.063* | |
Cl1 | 0.76886 (6) | 0.4977 (2) | 0.76187 (10) | 0.0713 (4) | |
N1 | 0.48941 (14) | 0.1662 (4) | 0.2660 (3) | 0.0379 (7) | |
O1 | 0.57014 (16) | −0.0733 (5) | 0.2551 (4) | 0.0704 (10) | |
O2 | 0.56815 (15) | 0.0226 (5) | 0.4436 (3) | 0.0658 (9) | |
O3 | 0.48162 (16) | 0.4517 (4) | 0.2627 (3) | 0.0652 (9) | |
S1 | 0.53270 (4) | −0.01249 (12) | 0.32646 (8) | 0.0425 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0282 (16) | 0.043 (2) | 0.0375 (19) | 0.0012 (14) | 0.0089 (15) | −0.0034 (15) |
C2 | 0.036 (2) | 0.055 (3) | 0.054 (2) | 0.0044 (18) | 0.0085 (19) | 0.0126 (19) |
C3 | 0.035 (2) | 0.070 (3) | 0.040 (2) | 0.0050 (19) | 0.0048 (16) | 0.0042 (19) |
C4 | 0.0293 (17) | 0.074 (3) | 0.064 (3) | −0.0003 (19) | 0.0094 (18) | −0.005 (2) |
C5 | 0.0349 (19) | 0.054 (3) | 0.050 (2) | −0.0066 (16) | 0.0133 (17) | −0.0024 (18) |
C6 | 0.0295 (16) | 0.042 (2) | 0.0350 (17) | −0.0029 (14) | 0.0053 (13) | −0.0059 (15) |
C7 | 0.0311 (18) | 0.068 (3) | 0.040 (2) | −0.0032 (18) | 0.0003 (16) | −0.0083 (19) |
C8 | 0.050 (2) | 0.086 (4) | 0.039 (2) | −0.003 (2) | 0.0138 (17) | −0.007 (2) |
C9 | 0.050 (3) | 0.078 (4) | 0.062 (3) | −0.019 (2) | 0.006 (2) | −0.027 (3) |
C10 | 0.0339 (18) | 0.042 (2) | 0.046 (2) | −0.0011 (16) | 0.0052 (16) | −0.0013 (17) |
C11 | 0.040 (2) | 0.040 (2) | 0.050 (2) | −0.0063 (16) | 0.0127 (17) | −0.0082 (17) |
C12 | 0.0341 (19) | 0.058 (3) | 0.064 (3) | −0.0119 (18) | 0.0193 (19) | −0.014 (2) |
C13 | 0.065 (3) | 0.094 (4) | 0.074 (3) | −0.021 (3) | 0.024 (3) | 0.007 (4) |
C14 | 0.040 (2) | 0.039 (2) | 0.069 (3) | −0.0104 (16) | 0.023 (2) | −0.0057 (19) |
C15 | 0.044 (2) | 0.073 (3) | 0.075 (3) | −0.001 (2) | 0.029 (2) | −0.020 (3) |
C16 | 0.032 (2) | 0.099 (4) | 0.082 (4) | 0.000 (2) | 0.011 (2) | −0.023 (3) |
C17 | 0.045 (2) | 0.053 (3) | 0.056 (2) | −0.0047 (19) | 0.0165 (19) | −0.002 (2) |
C18 | 0.045 (2) | 0.063 (3) | 0.060 (2) | −0.009 (2) | 0.0233 (18) | −0.009 (2) |
C19 | 0.0355 (19) | 0.049 (3) | 0.075 (3) | −0.0019 (17) | 0.0184 (19) | −0.009 (2) |
Cl1 | 0.0574 (6) | 0.0895 (9) | 0.0600 (7) | −0.0096 (7) | 0.0069 (5) | 0.0001 (7) |
N1 | 0.0274 (14) | 0.0417 (17) | 0.0414 (17) | −0.0041 (13) | 0.0053 (13) | −0.0031 (13) |
O1 | 0.0474 (17) | 0.065 (2) | 0.110 (3) | 0.0134 (15) | 0.0403 (19) | 0.0048 (19) |
O2 | 0.0575 (18) | 0.068 (2) | 0.0543 (17) | −0.0164 (16) | −0.0104 (14) | 0.0087 (16) |
O3 | 0.0473 (16) | 0.0416 (19) | 0.103 (3) | −0.0022 (13) | 0.0172 (17) | −0.0090 (16) |
S1 | 0.0290 (4) | 0.0460 (5) | 0.0476 (5) | 0.0002 (4) | 0.0041 (3) | 0.0030 (5) |
C1—N1 | 1.477 (4) | C10—S1 | 1.783 (4) |
C1—C6 | 1.535 (6) | C10—H10A | 0.9700 |
C1—C2 | 1.547 (5) | C10—H10B | 0.9700 |
C1—H1 | 0.9800 | C11—O3 | 1.209 (5) |
C2—C3 | 1.539 (6) | C11—N1 | 1.371 (5) |
C2—H2A | 0.9700 | C11—C12 | 1.528 (5) |
C2—H2B | 0.9700 | C12—C14 | 1.518 (6) |
C3—C7 | 1.544 (6) | C12—C13 | 1.544 (8) |
C3—C4 | 1.545 (6) | C12—H12 | 0.9800 |
C3—H3 | 0.9800 | C13—H13A | 0.9600 |
C4—C5 | 1.549 (6) | C13—H13B | 0.9600 |
C4—H4A | 0.9700 | C13—H13C | 0.9600 |
C4—H4B | 0.9700 | C14—C15 | 1.377 (6) |
C5—C6 | 1.541 (5) | C14—C19 | 1.380 (6) |
C5—H5A | 0.9700 | C15—C16 | 1.395 (7) |
C5—H5B | 0.9700 | C15—H15 | 0.9300 |
C6—C10 | 1.521 (5) | C16—C17 | 1.351 (7) |
C6—C7 | 1.561 (5) | C16—H16 | 0.9300 |
C7—C9 | 1.522 (7) | C17—C18 | 1.360 (6) |
C7—C8 | 1.538 (6) | C17—Cl1 | 1.749 (4) |
C8—H8A | 0.9600 | C18—C19 | 1.384 (6) |
C8—H8B | 0.9600 | C18—H18 | 0.9300 |
C8—H8C | 0.9600 | C19—H19 | 0.9300 |
C9—H9A | 0.9600 | N1—S1 | 1.706 (3) |
C9—H9B | 0.9600 | O1—S1 | 1.415 (4) |
C9—H9C | 0.9600 | O2—S1 | 1.417 (3) |
N1—C1—C6 | 107.4 (3) | C7—C9—H9C | 109.5 |
N1—C1—C2 | 116.2 (3) | H9A—C9—H9C | 109.5 |
C6—C1—C2 | 103.4 (3) | H9B—C9—H9C | 109.5 |
N1—C1—H1 | 109.8 | C6—C10—S1 | 107.0 (3) |
C6—C1—H1 | 109.8 | C6—C10—H10A | 110.3 |
C2—C1—H1 | 109.8 | S1—C10—H10A | 110.3 |
C3—C2—C1 | 102.2 (3) | C6—C10—H10B | 110.3 |
C3—C2—H2A | 111.3 | S1—C10—H10B | 110.3 |
C1—C2—H2A | 111.3 | H10A—C10—H10B | 108.6 |
C3—C2—H2B | 111.3 | O3—C11—N1 | 119.5 (4) |
C1—C2—H2B | 111.3 | O3—C11—C12 | 121.7 (4) |
H2A—C2—H2B | 109.2 | N1—C11—C12 | 118.6 (4) |
C2—C3—C7 | 102.7 (3) | C14—C12—C11 | 112.3 (3) |
C2—C3—C4 | 107.8 (4) | C14—C12—C13 | 110.8 (4) |
C7—C3—C4 | 102.3 (4) | C11—C12—C13 | 108.9 (4) |
C2—C3—H3 | 114.3 | C14—C12—H12 | 108.2 |
C7—C3—H3 | 114.3 | C11—C12—H12 | 108.2 |
C4—C3—H3 | 114.3 | C13—C12—H12 | 108.2 |
C3—C4—C5 | 103.6 (3) | C12—C13—H13A | 109.5 |
C3—C4—H4A | 111.0 | C12—C13—H13B | 109.5 |
C5—C4—H4A | 111.0 | H13A—C13—H13B | 109.5 |
C3—C4—H4B | 111.0 | C12—C13—H13C | 109.5 |
C5—C4—H4B | 111.0 | H13A—C13—H13C | 109.5 |
H4A—C4—H4B | 109.0 | H13B—C13—H13C | 109.5 |
C6—C5—C4 | 102.0 (3) | C15—C14—C19 | 117.4 (4) |
C6—C5—H5A | 111.4 | C15—C14—C12 | 118.3 (4) |
C4—C5—H5A | 111.4 | C19—C14—C12 | 124.2 (4) |
C6—C5—H5B | 111.4 | C14—C15—C16 | 121.6 (4) |
C4—C5—H5B | 111.4 | C14—C15—H15 | 119.2 |
H5A—C5—H5B | 109.2 | C16—C15—H15 | 119.2 |
C10—C6—C1 | 108.4 (3) | C17—C16—C15 | 118.9 (4) |
C10—C6—C5 | 116.8 (3) | C17—C16—H16 | 120.5 |
C1—C6—C5 | 105.4 (3) | C15—C16—H16 | 120.5 |
C10—C6—C7 | 118.5 (3) | C16—C17—C18 | 121.1 (4) |
C1—C6—C7 | 104.5 (3) | C16—C17—Cl1 | 119.6 (3) |
C5—C6—C7 | 101.9 (3) | C18—C17—Cl1 | 119.3 (3) |
C9—C7—C8 | 106.9 (4) | C17—C18—C19 | 119.7 (4) |
C9—C7—C3 | 115.0 (4) | C17—C18—H18 | 120.1 |
C8—C7—C3 | 113.4 (4) | C19—C18—H18 | 120.1 |
C9—C7—C6 | 113.1 (4) | C14—C19—C18 | 121.1 (4) |
C8—C7—C6 | 116.1 (3) | C14—C19—H19 | 119.4 |
C3—C7—C6 | 92.2 (3) | C18—C19—H19 | 119.4 |
C7—C8—H8A | 109.5 | C11—N1—C1 | 119.5 (3) |
C7—C8—H8B | 109.5 | C11—N1—S1 | 124.2 (3) |
H8A—C8—H8B | 109.5 | C1—N1—S1 | 111.8 (3) |
C7—C8—H8C | 109.5 | O1—S1—O2 | 116.8 (2) |
H8A—C8—H8C | 109.5 | O1—S1—N1 | 109.7 (2) |
H8B—C8—H8C | 109.5 | O2—S1—N1 | 109.0 (2) |
C7—C9—H9A | 109.5 | O1—S1—C10 | 112.6 (2) |
C7—C9—H9B | 109.5 | O2—S1—C10 | 110.9 (2) |
H9A—C9—H9B | 109.5 | N1—S1—C10 | 95.73 (16) |
N1—C1—C2—C3 | 124.3 (3) | N1—C11—C12—C14 | −103.2 (4) |
C6—C1—C2—C3 | 6.9 (4) | O3—C11—C12—C13 | −42.4 (6) |
C1—C2—C3—C7 | −41.2 (4) | N1—C11—C12—C13 | 133.6 (4) |
C1—C2—C3—C4 | 66.3 (4) | C11—C12—C14—C15 | 163.0 (4) |
C2—C3—C4—C5 | −73.6 (4) | C13—C12—C14—C15 | −75.0 (6) |
C7—C3—C4—C5 | 34.3 (4) | C11—C12—C14—C19 | −16.9 (6) |
C3—C4—C5—C6 | 2.8 (5) | C13—C12—C14—C19 | 105.2 (5) |
N1—C1—C6—C10 | 33.0 (4) | C19—C14—C15—C16 | 1.9 (8) |
C2—C1—C6—C10 | 156.4 (3) | C12—C14—C15—C16 | −178.0 (5) |
N1—C1—C6—C5 | 158.8 (3) | C14—C15—C16—C17 | −2.4 (9) |
C2—C1—C6—C5 | −77.8 (3) | C15—C16—C17—C18 | 3.0 (9) |
N1—C1—C6—C7 | −94.3 (3) | C15—C16—C17—Cl1 | −179.2 (4) |
C2—C1—C6—C7 | 29.1 (4) | C16—C17—C18—C19 | −3.0 (8) |
C4—C5—C6—C10 | −169.3 (4) | Cl1—C17—C18—C19 | 179.2 (4) |
C4—C5—C6—C1 | 70.3 (4) | C15—C14—C19—C18 | −1.9 (7) |
C4—C5—C6—C7 | −38.6 (4) | C12—C14—C19—C18 | 178.0 (5) |
C2—C3—C7—C9 | 173.1 (4) | C17—C18—C19—C14 | 2.4 (8) |
C4—C3—C7—C9 | 61.4 (5) | O3—C11—N1—C1 | −1.0 (6) |
C2—C3—C7—C8 | −63.5 (4) | C12—C11—N1—C1 | −177.0 (3) |
C4—C3—C7—C8 | −175.2 (3) | O3—C11—N1—S1 | −155.2 (4) |
C2—C3—C7—C6 | 56.3 (4) | C12—C11—N1—S1 | 28.7 (5) |
C4—C3—C7—C6 | −55.5 (3) | C6—C1—N1—C11 | 177.1 (3) |
C10—C6—C7—C9 | 69.0 (5) | C2—C1—N1—C11 | 61.9 (5) |
C1—C6—C7—C9 | −170.2 (4) | C6—C1—N1—S1 | −25.7 (4) |
C5—C6—C7—C9 | −60.7 (4) | C2—C1—N1—S1 | −140.9 (3) |
C10—C6—C7—C8 | −55.2 (5) | C11—N1—S1—O1 | −78.3 (4) |
C1—C6—C7—C8 | 65.6 (5) | C1—N1—S1—O1 | 125.7 (3) |
C5—C6—C7—C8 | 175.1 (4) | C11—N1—S1—O2 | 50.7 (4) |
C10—C6—C7—C3 | −172.6 (3) | C1—N1—S1—O2 | −105.2 (3) |
C1—C6—C7—C3 | −51.8 (3) | C11—N1—S1—C10 | 165.1 (3) |
C5—C6—C7—C3 | 57.7 (4) | C1—N1—S1—C10 | 9.2 (3) |
C1—C6—C10—S1 | −26.2 (4) | C6—C10—S1—O1 | −103.7 (3) |
C5—C6—C10—S1 | −145.0 (3) | C6—C10—S1—O2 | 123.2 (3) |
C7—C6—C10—S1 | 92.5 (4) | C6—C10—S1—N1 | 10.3 (3) |
O3—C11—C12—C14 | 80.8 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8B···N1 | 0.96 | 2.54 | 3.129 (6) | 120 |
C19—H19···O3 | 0.93 | 2.59 | 3.196 (6) | 123 |
C12—H12···O1 | 0.98 | 2.49 | 3.268 (6) | 137 |
C10—H10A···O3i | 0.97 | 2.36 | 3.292 (5) | 161 |
Symmetry code: (i) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C19H24ClNO3S |
Mr | 381.90 |
Crystal system, space group | Monoclinic, C2 |
Temperature (K) | 295 |
a, b, c (Å) | 21.0863 (16), 7.7948 (6), 12.102 (1) |
β (°) | 107.433 (1) |
V (Å3) | 1897.8 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.33 |
Crystal size (mm) | 0.30 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5780, 3715, 3146 |
Rint | 0.032 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.180, 1.10 |
No. of reflections | 3715 |
No. of parameters | 229 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.34, −0.22 |
Absolute structure | Flack (1983), 1503 Friedel pairs |
Absolute structure parameter | 0.27 (1) |
Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001).
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8B···N1 | 0.96 | 2.54 | 3.129 (6) | 119.6 |
C19—H19···O3 | 0.93 | 2.59 | 3.196 (6) | 122.8 |
C12—H12···O1 | 0.98 | 2.49 | 3.268 (6) | 136.7 |
C10—H10A···O3i | 0.97 | 2.36 | 3.292 (5) | 160.6 |
Symmetry code: (i) x, y−1, z. |
Acknowledgements
The authors acknowledge financial support from the National Natural Science Foundation of China (grant No. 20572029), the New Century Excellent Talents in Universities (grant No. NCET-04-0743), and the Cultivation Fund of the Key Scientific and Technical Innovation Project, Ministry of Education of China (grant No. 705039).
References
Boiadjiev, S. E. & Lightner, D. A. (2001). Tetrahedron Asymm. 12, 2551–2564. Web of Science CSD CrossRef CAS Google Scholar
Bruker (2001). SAINT-Plus (Version 6.45), SMART (Version 5.628) and SHELXTL (Version 6.14). Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Oppolzer, W. (1989). Tetrahedron Lett. 41, 5603–5606. CrossRef Web of Science Google Scholar
Oppolzer, W. (1990). Pure Appl. Chem. 62, 1241–1250. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
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Pioneering work of Oppolzer (1990) has resulted in the development of bornane[10,2]sultam serve as popular and widely used chiral auxiliaries in asymmetric synthesis. The resulting asymmetric induction using these auxiliaries are high in carbon-carbon bond formation such as alkylation (Oppolzer, 1989), and we have focused our attention on this field. In this paper, we present X-ray crystallographic analysis of the title compound, (I).
In (I), the six-membered ring of sultam shows a boat form (Fig. 1). The planes constructed by C3/C2/C1/C6and C3/C4/C5/C6 form a dihedral angle of 110.71°. The C7/C8/C9 plane makes dihedral angles of 93.92 and 90.93°, respectively, with C3/C2/C1/C6 and C3/C4/C5/C6 planes. Molecules are linked by the intermolecular C—H···O hydrogen bonds into a one-dimensional chain. No direction-specific interactions were observed between the adjacent chains along the b axis (Fig. 2).