(1S,2R,2′S,3′aS,5R)-2′-[(1S)-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

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 C₁₇H₃₀N₂O₃, (I). The S epimer, (II), is presented in the next article [Aouadi, Jeanneau & Praly (2007), Acta Cryst. E67, 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.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](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

---

Computing details

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).

(1S,2R,2'S,3'aS,5R)-2'-[(1R)-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

Crystal data

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) Å^3	Block, colourless
Z = 4	0.32 × 0.28 × 0.25 mm
F(000) = 680

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	H-atom parameters constrained
wR(F^2) = 0.127	w = 1/[σ^2(Fo^2) + (0.0653P)^2 + 0.3501P] where P = (Fo^2 + 2Fc^2)/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+0.001xFc^2λ^3/sin(2θ)]^-1/4
30 constraints	Extinction coefficient: 0.025 (5)

Special details

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H25···O1^i	0.82	1.96	2.763 (3)	168
C3—H31···O2	0.98	2.58	3.109 (4)	114
C11—H111···O2^ii	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.