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Cycloaddition of a (−)-menthone-derived nitrone to racemic but-3-en-2-ol led to two spirobicyclic heterocycles, with opposite configurations at the C atom attached to the OH group. This paper describes the
R epimer of the 1-hydroxyethyl substituent in imidazoisoxazole C
17H
30N
2O
3, (I). The
S epimer, (II), is presented in the next article [Aouadi, Jeanneau & Praly (2007),
Acta Cryst. E
67, o1327–o1329]. The absolute configurations of both epimers were assigned from the known configuration of the starting (−)-menthone derived nitrone. In (I), there is an O—H
O hydrogen bond (O—H
O = 1.96 Å and O—H
O = 168°) that links the molecules into left-handed helices along the
b axis. In addition, there are C—H
O and C—H
N hydrogen bonds.
Supporting information
CCDC reference: 606452
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.045
- wR factor = 0.126
- Data-to-parameter ratio = 10.4
checkCIF/PLATON results
No syntax errors found
Alert level G
REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values
From the CIF: _diffrn_reflns_theta_max 27.87
From the CIF: _reflns_number_total 2123
From the CIF: _diffrn_reflns_limit_ max hkl 13. 9. 21.
From the CIF: _diffrn_reflns_limit_ min hkl -13. -9. -16.
TEST1: Expected hkl limits for theta max
Calculated maximum hkl 13. 13. 22.
Calculated minimum hkl -13. -13. -22.
REFLT03_ALERT_4_G 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.
From the CIF: _diffrn_reflns_theta_max 27.87
From the CIF: _reflns_number_total 2123
Count of symmetry unique reflns 2140
Completeness (_total/calc) 99.21%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present no
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C15 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C16 = . R
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
0 ALERT level C = Check and explain
10 ALERT level G = General alerts; check
9 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: COLLECT (Nonius, 2001); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg & Putz, 1996); software used to prepare material for publication: WinGX (Farrugia, 1999).
(1
S,2
R,2'
S,3'aS,5
R)-2'-[(1
R)-1-Hydroxyethyl]-2-isopropyl-5,5'-dimethyl-
3',3'a-dihydro-2'
H-spiro[cyclohexane-1,6'-imidazo[1,5-
b]isoxazol]-4'(5'H)-one
top
Crystal data top
C17H30N2O3 | Dx = 1.187 Mg m−3 |
Mr = 310.43 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, P43 | Cell parameters from 1886 reflections |
Hall symbol: P 4cw | θ = 1.0–27.9° |
a = 10.1670 (2) Å | µ = 0.08 mm−1 |
c = 16.7997 (5) Å | T = 293 K |
V = 1736.55 (7) Å3 | Block, colourless |
Z = 4 | 0.32 × 0.28 × 0.25 mm |
F(000) = 680 | |
Data collection top
Nonius KappaCCD area-detector diffractometer | 1831 reflections with I > 2σ(I) |
Radiation source: sealed tube | Rint = 0.027 |
Graphite monochromator | θmax = 27.9°, θmin = 2° |
φ and ω scans | h = −13→13 |
3569 measured reflections | k = −9→9 |
2123 independent reflections | l = −16→21 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | H-atom parameters constrained |
wR(F2) = 0.127 | w = 1/[σ2(Fo2) + (0.0653P)2 + 0.3501P] where P = (Fo2 + 2Fc2)/3 |
S = 1.12 | (Δ/σ)max < 0.001 |
2123 reflections | Δρmax = 0.23 e Å−3 |
205 parameters | Δρmin = −0.24 e Å−3 |
1 restraint | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
30 constraints | Extinction coefficient: 0.025 (5) |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.8500 (3) | 0.2965 (3) | 0.46161 (16) | 0.0203 (6) | |
C2 | 0.8562 (3) | 0.1500 (3) | 0.47992 (17) | 0.0224 (6) | |
H21 | 0.9125 | 0.1077 | 0.441 | 0.034* | |
H22 | 0.7687 | 0.113 | 0.4744 | 0.034* | |
C3 | 0.9078 (3) | 0.1189 (3) | 0.56328 (17) | 0.0241 (6) | |
H31 | 0.9982 | 0.1517 | 0.5675 | 0.036* | |
C4 | 0.8235 (3) | 0.1897 (3) | 0.62491 (17) | 0.0275 (6) | |
H41 | 0.735 | 0.154 | 0.6237 | 0.041* | |
H42 | 0.8595 | 0.1743 | 0.6776 | 0.041* | |
C5 | 0.8181 (3) | 0.3368 (3) | 0.60912 (18) | 0.0280 (6) | |
H51 | 0.9057 | 0.3735 | 0.6145 | 0.042* | |
H52 | 0.7622 | 0.3783 | 0.6486 | 0.042* | |
C6 | 0.7650 (3) | 0.3678 (3) | 0.52548 (17) | 0.0240 (6) | |
H61 | 0.6782 | 0.3261 | 0.5229 | 0.036* | |
C7 | 0.9089 (3) | −0.0298 (3) | 0.57835 (19) | 0.0295 (7) | |
H71 | 0.8208 | −0.0632 | 0.5749 | 0.044* | |
H72 | 0.9437 | −0.047 | 0.6304 | 0.044* | |
H73 | 0.9628 | −0.0722 | 0.5391 | 0.044* | |
C8 | 0.7400 (3) | 0.5157 (3) | 0.51269 (19) | 0.0301 (7) | |
H81 | 0.7438 | 0.5326 | 0.4553 | 0.045* | |
C9 | 0.8411 (4) | 0.6059 (3) | 0.5530 (2) | 0.0407 (8) | |
H91 | 0.8276 | 0.6948 | 0.5357 | 0.061* | |
H92 | 0.9283 | 0.5782 | 0.5387 | 0.061* | |
H93 | 0.8308 | 0.601 | 0.6097 | 0.061* | |
C10 | 0.6008 (4) | 0.5510 (4) | 0.5411 (3) | 0.0483 (10) | |
H101 | 0.5913 | 0.5271 | 0.5961 | 0.072* | |
H102 | 0.5373 | 0.504 | 0.5098 | 0.072* | |
H103 | 0.5869 | 0.6438 | 0.5352 | 0.072* | |
C11 | 0.6660 (3) | 0.2706 (3) | 0.3555 (2) | 0.0286 (6) | |
H111 | 0.6774 | 0.2031 | 0.3162 | 0.043* | |
H112 | 0.6163 | 0.3419 | 0.3331 | 0.043* | |
H113 | 0.6197 | 0.2353 | 0.4005 | 0.043* | |
C12 | 0.8609 (3) | 0.4083 (3) | 0.33933 (17) | 0.0223 (6) | |
C13 | 0.9820 (3) | 0.4484 (3) | 0.38719 (17) | 0.0221 (6) | |
H131 | 0.9765 | 0.5407 | 0.4035 | 0.033* | |
C14 | 1.1095 (3) | 0.4217 (3) | 0.34251 (18) | 0.0247 (6) | |
H141 | 1.1006 | 0.4403 | 0.2861 | 0.037* | |
H142 | 1.1819 | 0.4727 | 0.3641 | 0.037* | |
C15 | 1.1276 (3) | 0.2765 (3) | 0.35767 (18) | 0.0245 (6) | |
H151 | 1.0711 | 0.2257 | 0.3218 | 0.037* | |
C16 | 1.2691 (3) | 0.2271 (3) | 0.35197 (18) | 0.0277 (6) | |
H161 | 1.2731 | 0.138 | 0.3741 | 0.042* | |
C17 | 1.3146 (3) | 0.2225 (4) | 0.2660 (2) | 0.0393 (8) | |
H171 | 1.2551 | 0.1693 | 0.2355 | 0.059* | |
H172 | 1.4013 | 0.1854 | 0.2635 | 0.059* | |
H173 | 1.3162 | 0.3101 | 0.2445 | 0.059* | |
O1 | 0.8323 (2) | 0.4530 (2) | 0.27319 (12) | 0.0294 (5) | |
O2 | 1.08450 (19) | 0.2598 (2) | 0.43861 (13) | 0.0255 (5) | |
O3 | 1.35480 (19) | 0.3087 (2) | 0.39579 (15) | 0.0322 (5) | |
H25 | 1.3758 | 0.2717 | 0.4372 | 0.048* | |
N1 | 0.7950 (2) | 0.3189 (2) | 0.38108 (14) | 0.0216 (5) | |
N2 | 0.9836 (2) | 0.3599 (2) | 0.45768 (14) | 0.0216 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0179 (12) | 0.0221 (13) | 0.0210 (13) | −0.0009 (10) | 0.0001 (10) | −0.0015 (11) |
C2 | 0.0217 (13) | 0.0215 (13) | 0.0240 (14) | −0.0013 (10) | −0.0007 (11) | −0.0006 (11) |
C3 | 0.0233 (14) | 0.0247 (14) | 0.0244 (14) | −0.0021 (11) | −0.0004 (11) | 0.0004 (11) |
C4 | 0.0317 (15) | 0.0292 (14) | 0.0216 (14) | −0.0037 (12) | 0.0013 (11) | 0.0021 (11) |
C5 | 0.0313 (15) | 0.0300 (15) | 0.0227 (14) | −0.0004 (12) | 0.0058 (12) | −0.0023 (12) |
C6 | 0.0228 (14) | 0.0238 (14) | 0.0254 (14) | 0.0013 (11) | 0.0046 (11) | −0.0014 (11) |
C7 | 0.0370 (16) | 0.0223 (14) | 0.0292 (16) | −0.0023 (12) | −0.0035 (13) | 0.0034 (12) |
C8 | 0.0366 (17) | 0.0244 (14) | 0.0291 (16) | 0.0083 (12) | 0.0118 (13) | 0.0006 (12) |
C9 | 0.062 (2) | 0.0243 (15) | 0.0360 (18) | −0.0062 (15) | 0.0115 (16) | −0.0046 (14) |
C10 | 0.049 (2) | 0.043 (2) | 0.053 (2) | 0.0183 (16) | 0.0237 (19) | 0.0070 (17) |
C11 | 0.0225 (14) | 0.0347 (16) | 0.0288 (15) | −0.0016 (12) | −0.0037 (12) | 0.0017 (12) |
C12 | 0.0231 (13) | 0.0202 (13) | 0.0236 (14) | 0.0038 (10) | −0.0002 (11) | −0.0008 (11) |
C13 | 0.0241 (13) | 0.0209 (12) | 0.0213 (13) | −0.0010 (10) | 0.0012 (11) | 0.0008 (11) |
C14 | 0.0257 (14) | 0.0252 (14) | 0.0230 (14) | −0.0012 (11) | 0.0018 (11) | 0.0046 (11) |
C15 | 0.0232 (13) | 0.0260 (14) | 0.0244 (14) | −0.0001 (10) | 0.0033 (11) | 0.0012 (11) |
C16 | 0.0230 (14) | 0.0339 (16) | 0.0264 (15) | 0.0026 (12) | 0.0029 (12) | 0.0035 (12) |
C17 | 0.0320 (17) | 0.052 (2) | 0.0341 (18) | 0.0082 (15) | 0.0089 (14) | −0.0022 (15) |
O1 | 0.0293 (11) | 0.0345 (11) | 0.0244 (10) | −0.0002 (9) | −0.0027 (8) | 0.0047 (9) |
O2 | 0.0216 (10) | 0.0289 (11) | 0.0261 (10) | 0.0055 (8) | 0.0044 (8) | 0.0074 (8) |
O3 | 0.0232 (10) | 0.0399 (12) | 0.0336 (12) | −0.0020 (9) | −0.0029 (9) | 0.0082 (10) |
N1 | 0.0181 (11) | 0.0255 (12) | 0.0211 (11) | −0.0003 (9) | −0.0014 (9) | −0.0003 (9) |
N2 | 0.0188 (11) | 0.0236 (12) | 0.0224 (12) | 0.0007 (9) | 0.0021 (9) | 0.0015 (9) |
Geometric parameters (Å, º) top
C1—N1 | 1.481 (4) | C10—H101 | 0.96 |
C1—N2 | 1.504 (3) | C10—H102 | 0.96 |
C1—C2 | 1.522 (4) | C10—H103 | 0.96 |
C1—C6 | 1.557 (4) | C11—N1 | 1.465 (4) |
C2—C3 | 1.529 (4) | C11—H111 | 0.96 |
C2—H21 | 0.97 | C11—H112 | 0.96 |
C2—H22 | 0.97 | C11—H113 | 0.96 |
C3—C4 | 1.525 (4) | C12—O1 | 1.235 (3) |
C3—C7 | 1.532 (4) | C12—N1 | 1.329 (4) |
C3—H31 | 0.98 | C12—C13 | 1.526 (4) |
C4—C5 | 1.520 (4) | C13—N2 | 1.487 (4) |
C4—H41 | 0.97 | C13—C14 | 1.522 (4) |
C4—H42 | 0.97 | C13—H131 | 0.98 |
C5—C6 | 1.538 (4) | C14—C15 | 1.509 (4) |
C5—H51 | 0.97 | C14—H141 | 0.97 |
C5—H52 | 0.97 | C14—H142 | 0.97 |
C6—C8 | 1.539 (4) | C15—O2 | 1.439 (4) |
C6—H61 | 0.98 | C15—C16 | 1.526 (4) |
C7—H71 | 0.96 | C15—H151 | 0.98 |
C7—H72 | 0.96 | C16—O3 | 1.411 (4) |
C7—H73 | 0.96 | C16—C17 | 1.518 (5) |
C8—C9 | 1.535 (5) | C16—H161 | 0.98 |
C8—C10 | 1.536 (4) | C17—H171 | 0.96 |
C8—H81 | 0.98 | C17—H172 | 0.96 |
C9—H91 | 0.96 | C17—H173 | 0.96 |
C9—H92 | 0.96 | O2—N2 | 1.480 (3) |
C9—H93 | 0.96 | O3—H25 | 0.82 |
| | | |
N1—C1—N2 | 103.6 (2) | C8—C10—H101 | 109.5 |
N1—C1—C2 | 110.5 (2) | C8—C10—H102 | 109.5 |
N2—C1—C2 | 113.0 (2) | H101—C10—H102 | 109.5 |
N1—C1—C6 | 110.4 (2) | C8—C10—H103 | 109.5 |
N2—C1—C6 | 109.4 (2) | H101—C10—H103 | 109.5 |
C2—C1—C6 | 109.8 (2) | H102—C10—H103 | 109.5 |
C1—C2—C3 | 113.7 (2) | N1—C11—H111 | 109.5 |
C1—C2—H21 | 108.8 | N1—C11—H112 | 109.5 |
C3—C2—H21 | 108.8 | H111—C11—H112 | 109.5 |
C1—C2—H22 | 108.8 | N1—C11—H113 | 109.5 |
C3—C2—H22 | 108.8 | H111—C11—H113 | 109.5 |
H21—C2—H22 | 107.7 | H112—C11—H113 | 109.5 |
C4—C3—C2 | 109.3 (2) | O1—C12—N1 | 127.4 (3) |
C4—C3—C7 | 110.9 (2) | O1—C12—C13 | 124.4 (3) |
C2—C3—C7 | 111.0 (2) | N1—C12—C13 | 108.1 (2) |
C4—C3—H31 | 108.5 | N2—C13—C14 | 106.0 (2) |
C2—C3—H31 | 108.5 | N2—C13—C12 | 105.4 (2) |
C7—C3—H31 | 108.5 | C14—C13—C12 | 112.3 (2) |
C5—C4—C3 | 111.5 (2) | N2—C13—H131 | 110.9 |
C5—C4—H41 | 109.3 | C14—C13—H131 | 110.9 |
C3—C4—H41 | 109.3 | C12—C13—H131 | 110.9 |
C5—C4—H42 | 109.3 | C15—C14—C13 | 101.2 (2) |
C3—C4—H42 | 109.3 | C15—C14—H141 | 111.5 |
H41—C4—H42 | 108 | C13—C14—H141 | 111.5 |
C4—C5—C6 | 111.9 (2) | C15—C14—H142 | 111.5 |
C4—C5—H51 | 109.2 | C13—C14—H142 | 111.5 |
C6—C5—H51 | 109.2 | H141—C14—H142 | 109.3 |
C4—C5—H52 | 109.2 | O2—C15—C14 | 103.8 (2) |
C6—C5—H52 | 109.2 | O2—C15—C16 | 107.9 (2) |
H51—C5—H52 | 107.9 | C14—C15—C16 | 115.2 (2) |
C5—C6—C8 | 112.7 (2) | O2—C15—H151 | 109.9 |
C5—C6—C1 | 109.8 (2) | C14—C15—H151 | 109.9 |
C8—C6—C1 | 116.8 (2) | C16—C15—H151 | 109.9 |
C5—C6—H61 | 105.5 | O3—C16—C17 | 109.0 (3) |
C8—C6—H61 | 105.5 | O3—C16—C15 | 110.8 (2) |
C1—C6—H61 | 105.5 | C17—C16—C15 | 110.9 (3) |
C3—C7—H71 | 109.5 | O3—C16—H161 | 108.7 |
C3—C7—H72 | 109.5 | C17—C16—H161 | 108.7 |
H71—C7—H72 | 109.5 | C15—C16—H161 | 108.7 |
C3—C7—H73 | 109.5 | C16—C17—H171 | 109.5 |
H71—C7—H73 | 109.5 | C16—C17—H172 | 109.5 |
H72—C7—H73 | 109.5 | H171—C17—H172 | 109.5 |
C9—C8—C10 | 109.9 (3) | C16—C17—H173 | 109.5 |
C9—C8—C6 | 114.3 (3) | H171—C17—H173 | 109.5 |
C10—C8—C6 | 109.7 (3) | H172—C17—H173 | 109.5 |
C9—C8—H81 | 107.6 | C15—O2—N2 | 109.53 (19) |
C10—C8—H81 | 107.6 | C16—O3—H25 | 109.5 |
C6—C8—H81 | 107.6 | C12—N1—C11 | 121.7 (2) |
C8—C9—H91 | 109.5 | C12—N1—C1 | 113.4 (2) |
C8—C9—H92 | 109.5 | C11—N1—C1 | 123.6 (2) |
H91—C9—H92 | 109.5 | O2—N2—C13 | 104.53 (19) |
C8—C9—H93 | 109.5 | O2—N2—C1 | 109.92 (19) |
H91—C9—H93 | 109.5 | C13—N2—C1 | 106.5 (2) |
H92—C9—H93 | 109.5 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H25···O1i | 0.82 | 1.96 | 2.763 (3) | 168 |
C3—H31···O2 | 0.98 | 2.58 | 3.109 (4) | 114 |
C11—H111···O2ii | 0.96 | 2.54 | 3.466 (4) | 162 |
C14—H142···O3 | 0.97 | 2.48 | 2.887 (4) | 105 |
C8—H81···N1 | 0.98 | 2.56 | 3.034 (4) | 110 |
Symmetry codes: (i) y+1, −x+1, z+1/4; (ii) −y+1, x−1, z−1/4. |
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