(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

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 S epimer of the 1-hydroxy­ethyl substituent in imidazoisoxazole C₁₇H₃₀N₂O₃, (I). The R epimer, (II), is presented in the previous article [Aouadi, Jeanneau & Praly (2007), Acta Cryst. E67, o1324–o1326]. 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 = 165°) that concatenates the mol­ecules 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 = 0.115
• Data-to-parameter ratio = 10.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.78 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C8

Alert level G
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           27.66
           From the CIF: _reflns_number_total               2247
           Count of symmetry unique reflns         2269
           Completeness (_total/calc)             99.03%
           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    = .          S

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   9 ALERT level G = General alerts; check

   9 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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	F(000) = 340
Mr = 310.43	Dx = 1.136 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1962 reflections
a = 10.7391 (9) Å	θ = 1.0–27.9°
b = 8.0956 (4) Å	µ = 0.08 mm^−1
c = 11.082 (1) Å	T = 293 K
β = 109.682 (3)°	Block, colourless
V = 907.2 (1) Å^3	0.20 × 0.19 × 0.12 mm
Z = 2

Data collection

Nonius KappaCCD area-detector diffractometer	1466 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.034
Graphite monochromator	θmax = 27.7°, θmin = 3.2°
φ and ω scans	h = −13→13
3904 measured reflections	k = −10→8
2247 independent reflections	l = −14→14

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) = 0.115	w = 1/[σ^2(Fo^2) + (0.0696P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.96	(Δ/σ)max < 0.001
2247 reflections	Δρmax = 0.16 e Å^−3
206 parameters	Δρmin = −0.17 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: 0.043 (8)

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	0.7238 (2)	0.2687 (3)	0.2941 (2)	0.0445 (6)
C2	0.7823 (2)	0.3689 (3)	0.4158 (2)	0.0499 (6)
H21	0.8715	0.4007	0.4229	0.075*
H22	0.7884	0.2985	0.4884	0.075*
C3	0.7059 (3)	0.5243 (3)	0.4253 (3)	0.0588 (7)
H31	0.7067	0.5996	0.3564	0.088*
C4	0.5624 (3)	0.4778 (4)	0.4055 (3)	0.0786 (9)
H41	0.5591	0.4081	0.4756	0.118*
H42	0.5117	0.577	0.4053	0.118*
C5	0.5023 (3)	0.3869 (4)	0.2796 (3)	0.0744 (9)
H51	0.5027	0.4587	0.2097	0.112*
H52	0.411	0.3599	0.2682	0.112*
C6	0.5773 (3)	0.2280 (4)	0.2741 (3)	0.0559 (7)
H61	0.5783	0.1631	0.349	0.084*
C7	0.7726 (4)	0.6106 (4)	0.5529 (3)	0.0805 (10)
H71	0.7227	0.7071	0.5582	0.121*
H72	0.8606	0.6424	0.5591	0.121*
H73	0.7763	0.5367	0.6218	0.121*
C8	0.5061 (3)	0.1193 (4)	0.1558 (3)	0.0693 (8)
H81	0.5732	0.0479	0.1411	0.104*
C9	0.4058 (4)	0.0062 (6)	0.1860 (4)	0.1181 (17)
H91	0.3404	0.0723	0.2047	0.177*
H92	0.4507	−0.0615	0.2588	0.177*
H93	0.3637	−0.063	0.1133	0.177*
C10	0.4387 (3)	0.2129 (6)	0.0315 (3)	0.0946 (12)
H101	0.4057	0.1357	−0.0378	0.142*
H102	0.5013	0.2855	0.0141	0.142*
H103	0.3665	0.2765	0.0397	0.142*
C11	0.8167 (3)	−0.0096 (4)	0.4012 (3)	0.0734 (9)
H111	0.8734	−0.0962	0.3909	0.11*
H112	0.8558	0.0408	0.4838	0.11*
H113	0.7321	−0.0549	0.3946	0.11*
C12	0.8339 (3)	0.0865 (3)	0.1996 (3)	0.0535 (7)
C13	0.7934 (2)	0.2316 (3)	0.1111 (3)	0.0497 (6)
H131	0.7298	0.1982	0.0283	0.074*
C14	0.9117 (3)	0.3191 (3)	0.0932 (3)	0.0532 (6)
H141	0.9831	0.2425	0.0994	0.08*
H142	0.8872	0.3763	0.0116	0.08*
C15	0.9490 (2)	0.4387 (3)	0.2041 (2)	0.0424 (6)
H151	0.9981	0.3808	0.2835	0.064*
C16	1.0247 (3)	0.5910 (3)	0.1897 (2)	0.0506 (6)
H161	0.9742	0.6494	0.111	0.076*
C17	1.1593 (3)	0.5429 (4)	0.1831 (3)	0.0744 (9)
H171	1.1475	0.4749	0.1091	0.112*
H172	1.208	0.4826	0.259	0.112*
H173	1.2074	0.6407	0.1771	0.112*
O1	0.8925 (2)	−0.0364 (3)	0.1781 (2)	0.0786 (6)
O2	0.82327 (16)	0.49123 (18)	0.20862 (16)	0.0471 (4)
O3	1.0445 (2)	0.6969 (2)	0.29582 (18)	0.0631 (5)
H25	0.9975	0.7788	0.2733	0.113 (16)*
N1	0.8001 (2)	0.1133 (2)	0.3022 (2)	0.0509 (5)
N2	0.73263 (19)	0.3515 (2)	0.17652 (19)	0.0456 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0427 (13)	0.0419 (13)	0.0458 (14)	0.0029 (10)	0.0109 (10)	0.0000 (11)
C2	0.0523 (14)	0.0495 (13)	0.0452 (14)	−0.0026 (11)	0.0129 (12)	−0.0013 (11)
C3	0.0751 (19)	0.0509 (14)	0.0567 (16)	−0.0015 (13)	0.0303 (14)	−0.0085 (12)
C4	0.078 (2)	0.0736 (19)	0.094 (2)	0.0056 (18)	0.0422 (19)	−0.0192 (19)
C5	0.0482 (16)	0.081 (2)	0.094 (2)	0.0070 (15)	0.0243 (16)	−0.0175 (18)
C6	0.0548 (16)	0.0566 (15)	0.0583 (16)	−0.0096 (12)	0.0216 (13)	−0.0107 (13)
C7	0.111 (3)	0.0675 (19)	0.069 (2)	−0.0150 (18)	0.0379 (18)	−0.0213 (17)
C8	0.0604 (18)	0.079 (2)	0.0672 (19)	−0.0212 (15)	0.0195 (14)	−0.0200 (17)
C9	0.105 (3)	0.142 (4)	0.118 (3)	−0.078 (3)	0.052 (3)	−0.050 (3)
C10	0.070 (2)	0.121 (3)	0.072 (2)	−0.013 (2)	−0.0019 (17)	−0.016 (2)
C11	0.099 (2)	0.0487 (16)	0.073 (2)	0.0058 (15)	0.0293 (18)	0.0148 (15)
C12	0.0570 (16)	0.0422 (14)	0.0581 (17)	0.0041 (12)	0.0149 (13)	−0.0046 (12)
C13	0.0560 (16)	0.0473 (14)	0.0425 (14)	0.0035 (11)	0.0126 (12)	−0.0082 (10)
C14	0.0630 (16)	0.0526 (15)	0.0478 (15)	0.0081 (12)	0.0235 (12)	−0.0013 (12)
C15	0.0400 (13)	0.0434 (13)	0.0441 (14)	0.0106 (9)	0.0146 (11)	0.0043 (10)
C16	0.0571 (15)	0.0486 (13)	0.0457 (14)	0.0069 (12)	0.0168 (12)	0.0066 (12)
C17	0.0593 (18)	0.0784 (19)	0.095 (2)	0.0064 (15)	0.0380 (17)	0.0156 (18)
O1	0.1058 (17)	0.0489 (11)	0.0866 (15)	0.0259 (11)	0.0396 (13)	−0.0024 (10)
O2	0.0476 (10)	0.0367 (9)	0.0591 (11)	0.0037 (7)	0.0209 (8)	−0.0023 (8)
O3	0.0702 (13)	0.0511 (11)	0.0614 (12)	−0.0013 (10)	0.0135 (10)	−0.0019 (9)
N1	0.0620 (13)	0.0370 (11)	0.0513 (13)	0.0054 (10)	0.0159 (10)	0.0025 (9)
N2	0.0470 (11)	0.0391 (10)	0.0477 (12)	0.0033 (8)	0.0121 (9)	−0.0012 (9)

Geometric parameters (Å, º)

C1—N1	1.488 (3)	C10—H101	0.96
C1—N2	1.497 (3)	C10—H102	0.96
C1—C2	1.517 (3)	C10—H103	0.96
C1—C6	1.548 (4)	C11—N1	1.447 (3)
C2—C3	1.525 (4)	C11—H111	0.96
C2—H21	0.97	C11—H112	0.96
C2—H22	0.97	C11—H113	0.96
C3—C7	1.522 (4)	C12—O1	1.242 (3)
C3—C4	1.528 (4)	C12—N1	1.323 (3)
C3—H31	0.98	C12—C13	1.497 (4)
C4—C5	1.516 (5)	C13—N2	1.487 (3)
C4—H41	0.97	C13—C14	1.525 (4)
C4—H42	0.97	C13—H131	0.98
C5—C6	1.529 (4)	C14—C15	1.509 (3)
C5—H51	0.97	C14—H141	0.97
C5—H52	0.97	C14—H142	0.97
C6—C8	1.551 (4)	C15—O2	1.432 (3)
C6—H61	0.98	C15—C16	1.515 (3)
C7—H71	0.96	C15—H151	0.98
C7—H72	0.96	C16—O3	1.413 (3)
C7—H73	0.96	C16—C17	1.522 (4)
C8—C10	1.525 (5)	C16—H161	0.98
C8—C9	1.533 (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	1.456 (3)
C9—H93	0.96	O3—H25	0.82
N1—C1—N2	103.63 (18)	C8—C10—H101	109.5
N1—C1—C2	110.11 (19)	C8—C10—H102	109.5
N2—C1—C2	113.97 (19)	H101—C10—H102	109.5
N1—C1—C6	109.9 (2)	C8—C10—H103	109.5
N2—C1—C6	109.3 (2)	H101—C10—H103	109.5
C2—C1—C6	109.7 (2)	H102—C10—H103	109.5
C1—C2—C3	115.5 (2)	N1—C11—H111	109.5
C1—C2—H21	108.4	N1—C11—H112	109.5
C3—C2—H21	108.4	H111—C11—H112	109.5
C1—C2—H22	108.4	N1—C11—H113	109.5
C3—C2—H22	108.4	H111—C11—H113	109.5
H21—C2—H22	107.5	H112—C11—H113	109.5
C7—C3—C2	110.3 (3)	O1—C12—N1	126.8 (3)
C7—C3—C4	112.5 (2)	O1—C12—C13	123.8 (2)
C2—C3—C4	109.0 (2)	N1—C12—C13	109.3 (2)
C7—C3—H31	108.3	N2—C13—C12	105.7 (2)
C2—C3—H31	108.3	N2—C13—C14	106.4 (2)
C4—C3—H31	108.3	C12—C13—C14	112.3 (2)
C5—C4—C3	110.4 (2)	N2—C13—H131	110.8
C5—C4—H41	109.6	C12—C13—H131	110.8
C3—C4—H41	109.6	C14—C13—H131	110.8
C5—C4—H42	109.6	C15—C14—C13	101.30 (19)
C3—C4—H42	109.6	C15—C14—H141	111.5
H41—C4—H42	108.1	C13—C14—H141	111.5
C4—C5—C6	112.2 (3)	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	102.98 (19)
C6—C5—H52	109.2	O2—C15—C16	107.97 (17)
H51—C5—H52	107.9	C14—C15—C16	116.14 (19)
C5—C6—C1	109.8 (2)	O2—C15—H151	109.8
C5—C6—C8	113.2 (3)	C14—C15—H151	109.8
C1—C6—C8	115.5 (2)	C16—C15—H151	109.8
C5—C6—H61	105.8	O3—C16—C15	109.94 (19)
C1—C6—H61	105.8	O3—C16—C17	108.5 (2)
C8—C6—H61	105.8	C15—C16—C17	110.5 (2)
C3—C7—H71	109.5	O3—C16—H161	109.3
C3—C7—H72	109.5	C15—C16—H161	109.3
H71—C7—H72	109.5	C17—C16—H161	109.3
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
C10—C8—C9	109.8 (3)	C16—C17—H173	109.5
C10—C8—C6	115.5 (3)	H171—C17—H173	109.5
C9—C8—C6	109.7 (3)	H172—C17—H173	109.5
C10—C8—H81	107.1	C15—O2—N2	108.74 (16)
C9—C8—H81	107.1	C16—O3—H25	109.5
C6—C8—H81	107.1	C12—N1—C11	122.6 (2)
C8—C9—H91	109.5	C12—N1—C1	113.1 (2)
C8—C9—H92	109.5	C11—N1—C1	123.5 (2)
H91—C9—H92	109.5	O2—N2—C13	105.02 (16)
C8—C9—H93	109.5	O2—N2—C1	111.62 (17)
H91—C9—H93	109.5	C13—N2—C1	107.42 (18)
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	2.756 (3)	165
C2—H22···O3^ii	0.97	2.59	3.406 (4)	142
C3—H31···O2	0.98	2.53	3.077 (4)	115
C8—H81···N1	0.98	2.54	3.026 (4)	110
C10—H102···N2	0.96	2.58	3.223 (5)	124
C11—H111···O1	0.96	2.49	2.860 (4)	103

Symmetry codes: (i) x, y+1, z; (ii) −x+2, y−1/2, −z+1.