Crystal structure of 2-isopropyl-5,7′-dimethyl-1′,3′,3a',6′,8a',8b'-hexa­hydro­spiro­[cyclo­hexane-1,6′-furo[3,4-d]imidazo[1,5-b]isoxazol]-8′(7′H)-one

Cyclo­addition reaction between a menthone-based chiral nitrone and 2,5-di­hydro­furan under microwave activation affords a enanti­opure cyclo­adduct in good yields and with high stereoselectivity

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.042
• wR factor = 0.096
• Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level B
PLAT910_ALERT_3_B Missing # of FCF Reflection(s) Below Theta(Min)          11 Note

Alert level C
STRVA01_ALERT_4_C           Flack test results are ambiguous.
           From the CIF: _refine_ls_abs_structure_Flack    0.600
           From the CIF: _refine_ls_abs_structure_Flack_su    0.300
PLAT907_ALERT_2_C Flack x > 0.5, Structure needs to be Inverted? .       0.60 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.596          4 Report

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details found  in the CIF     Please Do !
PLAT032_ALERT_4_G Std. Uncertainty on Flack Parameter Value High .      0.300 Report
PLAT791_ALERT_4_G The Model has Chirality at C3      (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G The Model has Chirality at C7      (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G The Model has Chirality at C8      (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G The Model has Chirality at C9      (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G The Model has Chirality at C14     (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G The Model has Chirality at C20     (Chiral SPGR)          R Verify
PLAT808_ALERT_5_G No Parseable SHELXL Style Weighting Scheme Found     Please Check
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) Still          80 %
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          2 Note
PLAT929_ALERT_5_G No Weight Pars,Obs and Calc R1,wR2,S not checked          ! Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  12 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   8 ALERT type 4 Improvement, methodology, query or suggestion
   3 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: CRYSTALS (Betteridge et al., 2003).

(I)

Crystal data

C17H28N2O3	F(000) = 672
Mr = 308.42	Dx = 1.236 Mg m^−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5548 reflections
a = 7.7474 (6) Å	θ = 4.5–66.7°
b = 11.1404 (8) Å	µ = 0.68 mm^−1
c = 19.208 (2) Å	T = 150 K
V = 1657.8 (2) Å^3	Block, colorless
Z = 4	0.49 × 0.43 × 0.25 mm

Data collection

Oxford Diffraction Xcalibur (Atlas, Gemini Ultra) diffractometer	2879 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray source	2680 reflections with I > 2.0σ(I)
Mirror monochromator	Rint = 0.059
Detector resolution: 10.4678 pixels mm^-1	θmax = 66.8°, θmin = 11°
ω scans	h = −9→8
Absorption correction: analytical [CrysAlis PRO (Agilent, 2013) based on expressions derived by Clark & Reid (1995); changes in illuminated volume were kept to a minimum, and were taken into account (Görbitz, 1999)]	k = −13→12
Tmin = 0.782, Tmax = 0.866	l = −22→21
10374 measured reflections

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	Method, part 1, Chebychev polynomial, (Watkin, 1994: Prince, 1982) [weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)] where Ai are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2]^2 Ai are: 0.124E + 04 0.195E + 04 0.105E + 04 304.
R[F^2 > 2σ(F^2)] = 0.042	(Δ/σ)max = 0.0002
wR(F^2) = 0.096	Δρmax = 0.16 e Å^−3
S = 1.03	Δρmin = −0.17 e Å^−3
2866 reflections	Extinction correction: Larson (1970), Equation 22
201 parameters	Extinction coefficient: 74 (4)
0 restraints	Absolute structure: Flack (1983), 1261 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.6 (3)
Hydrogen site location: difference Fourier map

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat with a nominal stability of 0.1K.

Refinement. The analytical numeric absorption correction using a multi-faceted crystal model is based on expressions derived by Clark & Reid (1995). The relatively large ratio of minimum to maximum corrections applied in the multi-scan process (1:nnn) reflect changes in the illuminated volume of the crystal. Changes in illuminated volume were kept to a minimum, and were taken into account (Görbitz, 1999).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.3924 (2)	0.46528 (13)	0.43226 (8)	0.0295
N2	0.2276 (2)	0.48439 (15)	0.39468 (9)	0.0248
C3	0.2216 (3)	0.39172 (18)	0.33856 (11)	0.0253
N4	0.3084 (3)	0.44977 (16)	0.27929 (9)	0.0257
C5	0.3388 (3)	0.3911 (2)	0.21315 (11)	0.0309
H51	0.3934	0.4467	0.1812	0.0471*
H53	0.2321	0.3682	0.1919	0.0466*
H52	0.4129	0.3213	0.2193	0.0470*
C6	0.3369 (3)	0.56800 (19)	0.28913 (11)	0.0269
C7	0.2626 (3)	0.60075 (18)	0.35923 (11)	0.0257
C8	0.3798 (3)	0.67280 (19)	0.40726 (12)	0.0279
C9	0.4274 (3)	0.5792 (2)	0.46276 (11)	0.0271
C10	0.3137 (4)	0.6110 (2)	0.52465 (12)	0.0372
O11	0.1969 (2)	0.70248 (16)	0.50158 (9)	0.0397
C12	0.2873 (3)	0.7679 (2)	0.44941 (13)	0.0352
H122	0.2094	0.8163	0.4202	0.0417*
H121	0.3689	0.8236	0.4714	0.0416*
H102	0.2495	0.5396	0.5410	0.0447*
H101	0.3821	0.6433	0.5635	0.0448*
H91	0.5499	0.5839	0.4753	0.0337*
H81	0.4758	0.7027	0.3812	0.0341*
H71	0.1551	0.6415	0.3518	0.0307*
O13	0.4052 (2)	0.63710 (15)	0.24780 (8)	0.0357
C14	0.0307 (3)	0.3616 (2)	0.32135 (11)	0.0274
C15	−0.0806 (3)	0.4686 (2)	0.29604 (12)	0.0310
C16	−0.2129 (4)	0.4250 (3)	0.24307 (14)	0.0435
H162	−0.2845	0.4937	0.2288	0.0654*
H163	−0.1594	0.3903	0.2017	0.0653*
H161	−0.2850	0.3629	0.2652	0.0658*
C17	−0.1731 (4)	0.5369 (2)	0.35403 (14)	0.0406
H171	−0.2186	0.6122	0.3336	0.0606*
H173	−0.2672	0.4908	0.3721	0.0604*
H172	−0.0979	0.5542	0.3931	0.0602*
H151	−0.0031	0.5263	0.2711	0.0372*
C18	−0.0536 (3)	0.2924 (2)	0.38122 (13)	0.0346
C19	0.0460 (4)	0.1795 (2)	0.40142 (14)	0.0379
C20	0.2339 (3)	0.2100 (2)	0.41916 (12)	0.0327
C21	0.3154 (3)	0.27553 (19)	0.35817 (12)	0.0288
H211	0.3096	0.2212	0.3171	0.0339*
H212	0.4342	0.2949	0.3684	0.0350*
C22	0.3387 (4)	0.0976 (2)	0.43654 (13)	0.0429
H222	0.4583	0.1173	0.4469	0.0645*
H221	0.3358	0.0416	0.3963	0.0629*
H223	0.2912	0.0549	0.4787	0.0629*
H201	0.2358	0.2644	0.4599	0.0385*
H192	0.0469	0.1237	0.3607	0.0463*
H191	−0.0113	0.1390	0.4418	0.0451*
H182	−0.1724	0.2721	0.3658	0.0423*
H181	−0.0606	0.3469	0.4217	0.0410*
H141	0.0390	0.3055	0.2810	0.0325*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0344 (8)	0.0232 (7)	0.0308 (8)	0.0026 (7)	−0.0085 (7)	−0.0014 (6)
N2	0.0304 (10)	0.0202 (9)	0.0239 (9)	0.0002 (8)	−0.0028 (8)	0.0005 (7)
C3	0.0324 (12)	0.0197 (10)	0.0237 (10)	0.0008 (9)	0.0029 (9)	−0.0011 (9)
N4	0.0317 (9)	0.0218 (9)	0.0236 (9)	−0.0001 (8)	0.0035 (8)	−0.0015 (7)
C5	0.0377 (12)	0.0307 (11)	0.0242 (11)	−0.0039 (10)	0.0039 (9)	−0.0034 (9)
C6	0.0290 (11)	0.0233 (10)	0.0284 (11)	−0.0006 (9)	−0.0018 (9)	0.0016 (9)
C7	0.0302 (11)	0.0206 (11)	0.0262 (10)	0.0023 (10)	0.0024 (9)	0.0014 (8)
C8	0.0324 (12)	0.0204 (10)	0.0307 (12)	−0.0016 (9)	0.0028 (10)	−0.0014 (9)
C9	0.0313 (11)	0.0233 (10)	0.0267 (10)	0.0000 (9)	−0.0042 (9)	−0.0040 (9)
C10	0.0453 (14)	0.0361 (13)	0.0302 (12)	−0.0014 (12)	−0.0002 (11)	−0.0035 (10)
O11	0.0392 (10)	0.0387 (9)	0.0413 (9)	0.0061 (8)	0.0076 (8)	−0.0078 (8)
C12	0.0421 (15)	0.0257 (11)	0.0377 (13)	0.0022 (11)	−0.0016 (11)	−0.0076 (10)
O13	0.0489 (10)	0.0280 (8)	0.0303 (8)	−0.0062 (8)	0.0057 (8)	0.0044 (6)
C14	0.0329 (11)	0.0228 (11)	0.0265 (11)	−0.0031 (9)	0.0021 (9)	−0.0005 (9)
C15	0.0295 (11)	0.0298 (12)	0.0335 (12)	−0.0022 (10)	−0.0007 (10)	0.0024 (9)
C16	0.0430 (14)	0.0423 (14)	0.0453 (14)	−0.0056 (13)	−0.0109 (13)	0.0027 (12)
C17	0.0370 (13)	0.0368 (13)	0.0481 (15)	0.0038 (12)	0.0041 (12)	−0.0022 (11)
C18	0.0371 (13)	0.0322 (13)	0.0344 (12)	−0.0047 (11)	0.0039 (11)	0.0025 (10)
C19	0.0533 (16)	0.0238 (12)	0.0365 (13)	−0.0085 (11)	0.0037 (12)	0.0039 (10)
C20	0.0495 (15)	0.0209 (11)	0.0278 (11)	−0.0015 (11)	−0.0011 (11)	−0.0001 (9)
C21	0.0360 (12)	0.0211 (11)	0.0292 (11)	0.0013 (10)	0.0009 (10)	−0.0008 (9)
C22	0.0680 (19)	0.0239 (12)	0.0369 (13)	0.0025 (12)	−0.0068 (13)	0.0040 (10)

Geometric parameters (Å, º)

O1—N2	1.482 (2)	C14—C15	1.550 (3)
O1—C9	1.424 (3)	C14—C18	1.531 (3)
N2—C3	1.493 (3)	C14—H141	0.997
N2—C7	1.489 (3)	C15—C16	1.524 (3)
C3—N4	1.472 (3)	C15—C17	1.527 (3)
C3—C14	1.552 (3)	C15—H151	1.001
C3—C21	1.531 (3)	C16—H162	0.983
N4—C5	1.448 (3)	C16—H163	0.977
N4—C6	1.349 (3)	C16—H161	0.986
C5—H51	0.969	C17—H171	0.991
C5—H53	0.956	C17—H173	0.957
C5—H52	0.974	C17—H172	0.970
C6—C7	1.509 (3)	C18—C19	1.526 (4)
C6—O13	1.226 (3)	C18—H182	0.992
C7—C8	1.523 (3)	C18—H181	0.988
C7—H71	0.959	C19—C20	1.533 (4)
C8—C9	1.536 (3)	C19—H192	0.999
C8—C12	1.513 (3)	C19—H191	1.001
C8—H81	0.957	C20—C21	1.518 (3)
C9—C10	1.521 (3)	C20—C22	1.529 (3)
C9—H91	0.980	C20—H201	0.990
C10—O11	1.433 (3)	C21—H211	0.996
C10—H102	0.989	C21—H212	0.966
C10—H101	0.983	C22—H222	0.972
O11—C12	1.423 (3)	C22—H221	0.995
C12—H122	0.985	C22—H223	1.009
C12—H121	0.981
N2—O1—C9	103.68 (14)	C3—C14—C18	110.82 (19)
O1—N2—C3	106.18 (15)	C15—C14—C18	112.69 (19)
O1—N2—C7	100.99 (15)	C3—C14—H141	103.9
C3—N2—C7	106.11 (15)	C15—C14—H141	105.9
N2—C3—N4	103.92 (16)	C18—C14—H141	107.2
N2—C3—C14	109.41 (17)	C14—C15—C16	109.79 (19)
N4—C3—C14	111.43 (18)	C14—C15—C17	114.5 (2)
N2—C3—C21	113.10 (17)	C16—C15—C17	109.3 (2)
N4—C3—C21	110.18 (18)	C14—C15—H151	108.1
C14—C3—C21	108.77 (18)	C16—C15—H151	106.8
C3—N4—C5	123.70 (17)	C17—C15—H151	108.1
C3—N4—C6	113.29 (17)	C15—C16—H162	108.5
C5—N4—C6	122.47 (19)	C15—C16—H163	112.6
N4—C5—H51	109.8	H162—C16—H163	108.7
N4—C5—H53	110.8	C15—C16—H161	108.4
H51—C5—H53	106.1	H162—C16—H161	110.3
N4—C5—H52	110.4	H163—C16—H161	108.3
H51—C5—H52	109.2	C15—C17—H171	107.4
H53—C5—H52	110.4	C15—C17—H173	110.8
N4—C6—C7	107.39 (18)	H171—C17—H173	109.1
N4—C6—O13	126.4 (2)	C15—C17—H172	112.4
C7—C6—O13	126.2 (2)	H171—C17—H172	110.5
C6—C7—N2	105.48 (16)	H173—C17—H172	106.5
C6—C7—C8	116.15 (19)	C14—C18—C19	113.0 (2)
N2—C7—C8	106.89 (17)	C14—C18—H182	106.7
C6—C7—H71	108.3	C19—C18—H182	110.9
N2—C7—H71	108.7	C14—C18—H181	107.8
C8—C7—H71	111.0	C19—C18—H181	109.5
C7—C8—C9	101.88 (16)	H182—C18—H181	108.9
C7—C8—C12	114.2 (2)	C18—C19—C20	110.74 (19)
C9—C8—C12	102.57 (18)	C18—C19—H192	108.4
C7—C8—H81	109.3	C20—C19—H192	107.8
C9—C8—H81	114.4	C18—C19—H191	110.1
C12—C8—H81	113.9	C20—C19—H191	110.4
C8—C9—O1	105.88 (16)	H192—C19—H191	109.2
C8—C9—C10	104.18 (18)	C19—C20—C21	109.3 (2)
O1—C9—C10	114.75 (19)	C19—C20—C22	111.8 (2)
C8—C9—H91	111.5	C21—C20—C22	110.0 (2)
O1—C9—H91	109.5	C19—C20—H201	109.0
C10—C9—H91	110.8	C21—C20—H201	108.1
C9—C10—O11	106.84 (18)	C22—C20—H201	108.7
C9—C10—H102	110.7	C3—C21—C20	113.52 (19)
O11—C10—H102	110.6	C3—C21—H211	107.3
C9—C10—H101	111.5	C20—C21—H211	107.5
O11—C10—H101	108.3	C3—C21—H212	108.2
H102—C10—H101	108.9	C20—C21—H212	110.3
C10—O11—C12	105.74 (19)	H211—C21—H212	109.9
C8—C12—O11	104.57 (19)	C20—C22—H222	111.5
C8—C12—H122	111.7	C20—C22—H221	109.4
O11—C12—H122	112.4	H222—C22—H221	108.8
C8—C12—H121	111.6	C20—C22—H223	111.6
O11—C12—H121	109.7	H222—C22—H223	106.8
H122—C12—H121	107.0	H221—C22—H223	108.7
C3—C14—C15	115.54 (18)
C9—O1—N2—C3	156.12 (16)	C21—C3—C14—C18	53.8 (2)
C9—O1—N2—C7	45.58 (18)	N2—C3—C21—C20	64.1 (2)
N2—O1—C9—C8	−40.8 (2)	N4—C3—C21—C20	179.91 (18)
N2—O1—C9—C10	73.5 (2)	C14—C3—C21—C20	−57.7 (2)
C12—O11—C10—C9	−30.4 (2)	O13—C6—C7—N2	−169.1 (2)
C10—O11—C12—C8	41.4 (2)	O13—C6—C7—C8	−51.0 (3)
O1—N2—C3—N4	−88.72 (18)	N4—C6—C7—N2	13.2 (2)
O1—N2—C3—C14	152.15 (15)	N4—C6—C7—C8	131.3 (2)
O1—N2—C3—C21	30.7 (2)	N2—C7—C8—C9	9.3 (2)
C7—N2—C3—N4	18.2 (2)	N2—C7—C8—C12	−100.5 (2)
C7—N2—C3—C14	−100.94 (18)	C6—C7—C8—C9	−108.1 (2)
C7—N2—C3—C21	137.64 (18)	C6—C7—C8—C12	142.1 (2)
O1—N2—C7—C6	91.23 (18)	C7—C8—C9—O1	19.2 (2)
O1—N2—C7—C8	−32.94 (19)	C7—C8—C9—C10	−102.2 (2)
C3—N2—C7—C6	−19.4 (2)	C12—C8—C9—O1	137.68 (18)
C3—N2—C7—C8	−143.56 (17)	C12—C8—C9—C10	16.3 (2)
C5—N4—C3—N2	177.7 (2)	C7—C8—C12—O11	74.2 (2)
C5—N4—C3—C14	−64.6 (3)	C9—C8—C12—O11	−35.1 (2)
C5—N4—C3—C21	56.2 (3)	O1—C9—C10—O11	−107.8 (2)
C6—N4—C3—N2	−10.6 (3)	C8—C9—C10—O11	7.6 (2)
C6—N4—C3—C14	107.2 (2)	C3—C14—C15—C16	146.3 (2)
C6—N4—C3—C21	−132.0 (2)	C3—C14—C15—C17	−90.4 (2)
C3—N4—C6—O13	−179.3 (2)	C18—C14—C15—C16	−84.9 (2)
C3—N4—C6—C7	−1.6 (3)	C18—C14—C15—C17	38.4 (3)
C5—N4—C6—O13	−7.4 (4)	C3—C14—C18—C19	−54.8 (3)
C5—N4—C6—C7	170.3 (2)	C15—C14—C18—C19	174.06 (19)
N2—C3—C14—C15	59.5 (2)	C14—C18—C19—C20	55.5 (3)
N2—C3—C14—C18	−70.2 (2)	C18—C19—C20—C21	−55.6 (3)
N4—C3—C14—C15	−54.8 (2)	C18—C19—C20—C22	−177.5 (2)
N4—C3—C14—C18	175.48 (17)	C19—C20—C21—C3	58.7 (2)
C21—C3—C14—C15	−176.47 (18)	C22—C20—C21—C3	−178.24 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H52···O13^i	0.97	2.57	3.536 (3)	172

Symmetry code: (i) −x+1, y−1/2, −z+1/2.