8,9-Isopropyl­idenedi­oxy-3-p-tolyl-1,6-dioxa-3-aza­spiro­[4.5]decane-2,10-dione

Ling, C.-S.; Wu, Q.; Li, S.-S.

doi:10.1107/S1600536808034259

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2181

doi:10.1107/S1600536808034259

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8,9-Isopropylidenedioxy-3-p-tolyl-1,6-dioxa-3-azaspiro[4.5]decane-2,10-dione

Chun-Sheng Ling,^a Qiang Wu ^b ^* and Shan-Shan Li ^c

^aPharmaceutical College of Henan University, Kaifeng 475004, People's Republic of China, ^bInstitute of Pharmacy, Henan University, Kaifeng 475004, People's Republic of China, and ^cCollege of Chemistry and Environmental Engineering, Beijing Technology and Business University, Beijing 100037, People's Republic of China
^*Correspondence e-mail: ysywu@126.com

(Received 13 October 2008; accepted 20 October 2008; online 25 October 2008)

In the title compound, C₁₇H₁₉NO₆, which may serve as a ketone catalyst for the asymmetric epoxidation of olefins, the crystal packing is consolidated by C—H⋯O interactions.

Related literature

For general background, see: Denmark & Wu (1999 ); Shi (2004 ); Yang (2004 ). For the synthesis, see: Zhao et al. (2006 ).

Experimental

Crystal data

C₁₇H₁₉NO₆
M_r = 333.33
Monoclinic, P 2₁
a = 11.1268 (8) Å
b = 6.3163 (5) Å
c = 11.8697 (8) Å
β = 94.084 (1)°
V = 832.09 (11) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 (2) K
0.18 × 0.15 × 0.13 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ) T_min = 0.982, T_max = 0.987
8821 measured reflections
1795 independent reflections
1389 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.075
S = 1.06
1795 reflections
220 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.10 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9B⋯O1ⁱ	0.97	2.54	3.093 (3)	116
C14—H14B⋯O4ⁱⁱ	0.97	2.55	3.426 (3)	151
Symmetry codes: (i) $[-x+2, y-{\script{1\over 2}}, -z]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808034259/hb2819sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808034259/hb2819Isup2.hkl

checkCIF report

Comment top

Dioxiranes generated in situ from chiral ketones are effective for the asymmetric epoxidation of olefins (Denmark & Wu, 1999; Shi, 2004; Yang, 2004). As part of our own studies in this area, we now report the synthesis and structure of the title compound, (I).

The compound (I) consists of a four-ring system, including a phenyl ring, a pyran ring, a dioxolane ring and an oxazolidine ring, and which displays a chair molecular framework (Fig. 1). In the structure of (I), the S(6) ring of O4/C10/C11/C12/C13/C14 is nonplanar, charactrtized by a O4–C10–C11–C12 torsion angle of 61.1 (2) °. The stereogenic centres C10, C12 and C13 were assigned R, S, and S configurations, respectively.

In the crystal, some short C—H···O interactions (Table 1) may help to establish the packing (Fig. 2).

Related literature top

For general background, see: Denmark & Wu (1999); Shi (2004); Yang (2004). For the synthesis, see: Zhao et al. (2006).

Experimental top

The title compound was made by the method of Zhao et al. (2006), starting from D-glucose and 4-methyl-benzenamine to yield colorless blocks of (I). The molecular formula, C₁₇H₁₉NO₆, was established by ESI-MS, m/z: 356(M+Na), 334(M+H), 232, 204, 108. Spectroscopic analysis, 1H NMR (400 MHz, CDCl₃): δ 7.40 (d, J=5.4 Hz, 2H, ArH), 7.19 (d, J=5.4 Hz, 2H, ArH), 4.87 (d, J=5.7 Hz, 1H), 4.74 (d, J=10.2 Hz, 1H), 4.66–4.61 (m, 2H), 4.27 (d, J=13.8 Hz, 1H), 3.74 (d, J=10.2 Hz, 1H), 2.34 (s, 3H, ArCH₃), 1.49 (s, 3H, –CH₃), 1.44 (s, 3H, –CH₃).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of (I) with displacement ellipsoids for the non-hydrogen atoms drawn at the 50% probability level.
	Fig. 2. Packing of the title compound (I), H atoms are omitted for clarity.
	Fig. 3. The formation of the title compound.

8,9-Isopropylidenedioxy-3-p-tolyl-1,6-dioxa-3-azaspiro[4.5]decane-2,10-dione top

Crystal data top

C₁₇H₁₉NO₆	F(000) = 352
M_r = 333.33	D_x = 1.330 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2y b	Cell parameters from 2427 reflections
a = 11.1268 (8) Å	θ = 2.4–21.1°
b = 6.3163 (5) Å	µ = 0.10 mm⁻¹
c = 11.8697 (8) Å	T = 296 K
β = 94.084 (1)°	Block, colorless
V = 832.09 (11) Å³	0.18 × 0.15 × 0.13 mm
Z = 2

Data collection top

Bruker SMART CCD diffractometer	1795 independent reflections
Radiation source: fine-focus sealed tube	1389 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ω scans	θ_max = 26.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −13→13
T_min = 0.982, T_max = 0.987	k = −7→7
8821 measured reflections	l = −14→14

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.075	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0303P)² + 0.0894P] where P = (F_o² + 2F_c²)/3
1795 reflections	(Δ/σ)_max < 0.001
220 parameters	Δρ_max = 0.10 e Å⁻³
1 restraint	Δρ_min = −0.13 e Å⁻³

Crystal data top

C₁₇H₁₉NO₆	V = 832.09 (11) Å³
M_r = 333.33	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 11.1268 (8) Å	µ = 0.10 mm⁻¹
b = 6.3163 (5) Å	T = 296 K
c = 11.8697 (8) Å	0.18 × 0.15 × 0.13 mm
β = 94.084 (1)°

Data collection top

Bruker SMART CCD diffractometer	1795 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	1389 reflections with I > 2σ(I)
T_min = 0.982, T_max = 0.987	R_int = 0.028
8821 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	1 restraint
wR(F²) = 0.075	H-atom parameters constrained
S = 1.06	Δρ_max = 0.10 e Å⁻³
1795 reflections	Δρ_min = −0.13 e Å⁻³
220 parameters

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.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.89223 (17)	0.9579 (3)	0.12879 (17)	0.0543 (5)
O1	1.00555 (17)	1.2504 (3)	0.08456 (16)	0.0792 (6)
O2	0.84070 (14)	1.1560 (3)	−0.02227 (14)	0.0588 (5)
O3	0.70022 (18)	0.7396 (3)	−0.15295 (19)	0.0810 (6)
O4	0.64278 (14)	1.1097 (3)	0.02397 (14)	0.0600 (5)
O5	0.47051 (15)	1.1373 (3)	−0.18543 (15)	0.0665 (5)
O6	0.59983 (16)	1.0190 (4)	−0.31240 (15)	0.0766 (6)
C1	1.1700 (3)	0.5776 (7)	0.5018 (3)	0.0997 (12)
H1A	1.1778	0.6722	0.5652	0.150*
H1B	1.2484	0.5455	0.4775	0.150*
H1C	1.1316	0.4492	0.5235	0.150*
C2	1.0944 (3)	0.6815 (5)	0.4059 (2)	0.0705 (8)
C3	1.0017 (3)	0.5773 (5)	0.3486 (2)	0.0760 (8)
H3	0.9824	0.4413	0.3714	0.091*
C4	0.9355 (3)	0.6666 (5)	0.2580 (2)	0.0687 (8)
H4	0.8727	0.5907	0.2212	0.082*
C5	0.9620 (2)	0.8692 (4)	0.2214 (2)	0.0534 (6)
C6	1.0555 (2)	0.9785 (5)	0.2790 (2)	0.0648 (7)
H6	1.0751	1.1145	0.2567	0.078*
C7	1.1195 (2)	0.8837 (6)	0.3702 (2)	0.0727 (8)
H7	1.1815	0.9590	0.4086	0.087*
C8	0.9231 (2)	1.1294 (4)	0.0685 (2)	0.0563 (6)
C9	0.7901 (2)	0.8463 (4)	0.0715 (2)	0.0568 (6)
H9A	0.7294	0.8121	0.1234	0.068*
H9B	0.8156	0.7175	0.0357	0.068*
C10	0.74453 (19)	1.0086 (4)	−0.0148 (2)	0.0524 (6)
C11	0.7064 (2)	0.9266 (4)	−0.1330 (2)	0.0566 (6)
C12	0.6676 (2)	1.0984 (5)	−0.2160 (2)	0.0628 (7)
H12	0.7381	1.1759	−0.2389	0.075*
C13	0.5811 (2)	1.2495 (4)	−0.1640 (2)	0.0647 (7)
H13	0.5778	1.3830	−0.2062	0.078*
C14	0.6057 (2)	1.2941 (4)	−0.0408 (2)	0.0677 (7)
H14A	0.6684	1.4007	−0.0314	0.081*
H14B	0.5335	1.3517	−0.0114	0.081*
C15	0.4747 (2)	1.0412 (5)	−0.2935 (2)	0.0696 (8)
C16	0.4154 (3)	1.1789 (7)	−0.3854 (3)	0.1116 (13)
H16A	0.3316	1.1956	−0.3732	0.167*
H16B	0.4234	1.1136	−0.4576	0.167*
H16C	0.4537	1.3152	−0.3840	0.167*
C17	0.4167 (3)	0.8262 (6)	−0.2888 (3)	0.0914 (10)
H17A	0.4574	0.7441	−0.2296	0.137*
H17B	0.4222	0.7553	−0.3597	0.137*
H17C	0.3335	0.8422	−0.2739	0.137*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0565 (12)	0.0435 (12)	0.0639 (12)	−0.0099 (10)	0.0112 (10)	−0.0006 (10)
O1	0.0775 (12)	0.0680 (12)	0.0918 (13)	−0.0344 (12)	0.0032 (10)	0.0086 (11)
O2	0.0532 (9)	0.0492 (10)	0.0746 (11)	−0.0102 (8)	0.0097 (8)	0.0076 (9)
O3	0.0798 (13)	0.0514 (12)	0.1092 (15)	0.0067 (11)	−0.0109 (11)	−0.0152 (12)
O4	0.0554 (9)	0.0535 (11)	0.0729 (11)	0.0052 (9)	0.0179 (8)	0.0002 (9)
O5	0.0617 (10)	0.0617 (11)	0.0763 (12)	0.0064 (10)	0.0058 (8)	−0.0065 (11)
O6	0.0769 (12)	0.0874 (14)	0.0670 (11)	0.0026 (12)	0.0163 (10)	−0.0039 (11)
C1	0.087 (2)	0.131 (3)	0.082 (2)	0.014 (2)	0.0079 (17)	0.023 (2)
C2	0.0640 (17)	0.081 (2)	0.0681 (18)	0.0086 (16)	0.0169 (14)	0.0026 (16)
C3	0.089 (2)	0.0619 (19)	0.0775 (19)	0.0032 (17)	0.0113 (16)	0.0108 (16)
C4	0.0782 (18)	0.0552 (17)	0.0727 (18)	−0.0080 (15)	0.0053 (14)	−0.0008 (16)
C5	0.0565 (14)	0.0485 (15)	0.0563 (15)	0.0007 (12)	0.0131 (12)	−0.0047 (12)
C6	0.0637 (16)	0.0599 (17)	0.0719 (17)	−0.0069 (14)	0.0128 (14)	−0.0061 (15)
C7	0.0608 (17)	0.088 (2)	0.0695 (19)	−0.0023 (17)	0.0066 (14)	−0.0095 (17)
C8	0.0560 (14)	0.0470 (15)	0.0672 (15)	−0.0056 (14)	0.0142 (12)	−0.0002 (14)
C9	0.0501 (13)	0.0438 (13)	0.0771 (16)	−0.0094 (12)	0.0082 (12)	0.0038 (13)
C10	0.0439 (12)	0.0439 (13)	0.0708 (16)	−0.0061 (12)	0.0147 (11)	0.0010 (12)
C11	0.0418 (13)	0.0497 (15)	0.0799 (18)	−0.0014 (11)	0.0168 (12)	−0.0023 (14)
C12	0.0629 (15)	0.0604 (16)	0.0671 (16)	−0.0096 (14)	0.0182 (13)	0.0037 (14)
C13	0.0712 (17)	0.0429 (14)	0.0803 (19)	0.0024 (14)	0.0080 (14)	0.0057 (15)
C14	0.0699 (17)	0.0472 (16)	0.086 (2)	0.0098 (14)	0.0052 (14)	−0.0095 (15)
C15	0.0694 (18)	0.0691 (19)	0.0700 (18)	0.0084 (15)	0.0032 (14)	0.0037 (16)
C16	0.131 (3)	0.108 (3)	0.093 (2)	0.025 (3)	−0.012 (2)	0.023 (2)
C17	0.086 (2)	0.084 (3)	0.104 (2)	−0.009 (2)	0.0007 (18)	−0.012 (2)

Geometric parameters (Å, º) top

N1—C8	1.356 (3)	C5—C6	1.387 (3)
N1—C5	1.415 (3)	C6—C7	1.389 (4)
N1—C9	1.463 (3)	C6—H6	0.9300
O1—C8	1.199 (3)	C7—H7	0.9300
O2—C8	1.374 (3)	C9—C10	1.511 (3)
O2—C10	1.426 (3)	C9—H9A	0.9700
O3—C11	1.205 (3)	C9—H9B	0.9700
O4—C10	1.405 (3)	C10—C11	1.528 (4)
O4—C14	1.440 (3)	C11—C12	1.508 (4)
O5—C15	1.423 (3)	C12—C13	1.517 (4)
O5—C13	1.427 (3)	C12—H12	0.9800
O6—C12	1.417 (3)	C13—C14	1.495 (4)
O6—C15	1.432 (3)	C13—H13	0.9800
C1—C2	1.516 (4)	C14—H14A	0.9700
C1—H1A	0.9600	C14—H14B	0.9700
C1—H1B	0.9600	C15—C17	1.506 (4)
C1—H1C	0.9600	C15—C16	1.510 (4)
C2—C3	1.364 (4)	C16—H16A	0.9600
C2—C7	1.380 (5)	C16—H16B	0.9600
C3—C4	1.380 (4)	C16—H16C	0.9600
C3—H3	0.9300	C17—H17A	0.9600
C4—C5	1.390 (4)	C17—H17B	0.9600
C4—H4	0.9300	C17—H17C	0.9600

C8—N1—C5	125.5 (2)	O4—C10—C11	106.10 (18)
C8—N1—C9	110.9 (2)	O2—C10—C11	108.94 (19)
C5—N1—C9	122.3 (2)	C9—C10—C11	116.8 (2)
C8—O2—C10	109.46 (18)	O3—C11—C12	124.6 (3)
C10—O4—C14	113.54 (19)	O3—C11—C10	121.4 (3)
C15—O5—C13	106.81 (19)	C12—C11—C10	113.8 (2)
C12—O6—C15	107.8 (2)	O6—C12—C11	112.6 (2)
C2—C1—H1A	109.5	O6—C12—C13	103.6 (2)
C2—C1—H1B	109.5	C11—C12—C13	110.3 (2)
H1A—C1—H1B	109.5	O6—C12—H12	110.1
C2—C1—H1C	109.5	C11—C12—H12	110.1
H1A—C1—H1C	109.5	C13—C12—H12	110.1
H1B—C1—H1C	109.5	O5—C13—C14	111.3 (2)
C3—C2—C7	117.1 (3)	O5—C13—C12	100.3 (2)
C3—C2—C1	121.7 (3)	C14—C13—C12	116.0 (2)
C7—C2—C1	121.2 (3)	O5—C13—H13	109.6
C2—C3—C4	122.3 (3)	C14—C13—H13	109.6
C2—C3—H3	118.9	C12—C13—H13	109.6
C4—C3—H3	118.9	O4—C14—C13	113.3 (2)
C3—C4—C5	120.4 (3)	O4—C14—H14A	108.9
C3—C4—H4	119.8	C13—C14—H14A	108.9
C5—C4—H4	119.8	O4—C14—H14B	108.9
C6—C5—C4	118.2 (3)	C13—C14—H14B	108.9
C6—C5—N1	122.4 (2)	H14A—C14—H14B	107.7
C4—C5—N1	119.4 (2)	O5—C15—O6	106.1 (2)
C5—C6—C7	119.7 (3)	O5—C15—C17	108.0 (3)
C5—C6—H6	120.2	O6—C15—C17	110.0 (2)
C7—C6—H6	120.2	O5—C15—C16	111.4 (3)
C2—C7—C6	122.3 (3)	O6—C15—C16	108.8 (3)
C2—C7—H7	118.9	C17—C15—C16	112.3 (3)
C6—C7—H7	118.9	C15—C16—H16A	109.5
O1—C8—N1	130.1 (2)	C15—C16—H16B	109.5
O1—C8—O2	120.5 (2)	H16A—C16—H16B	109.5
N1—C8—O2	109.4 (2)	C15—C16—H16C	109.5
N1—C9—C10	101.55 (19)	H16A—C16—H16C	109.5
N1—C9—H9A	111.5	H16B—C16—H16C	109.5
C10—C9—H9A	111.5	C15—C17—H17A	109.5
N1—C9—H9B	111.5	C15—C17—H17B	109.5
C10—C9—H9B	111.5	H17A—C17—H17B	109.5
H9A—C9—H9B	109.3	C15—C17—H17C	109.5
O4—C10—O2	110.5 (2)	H17A—C17—H17C	109.5
O4—C10—C9	109.00 (19)	H17B—C17—H17C	109.5
O2—C10—C9	105.54 (17)

C7—C2—C3—C4	0.6 (4)	N1—C9—C10—O2	17.4 (2)
C1—C2—C3—C4	−177.1 (3)	N1—C9—C10—C11	138.56 (19)
C2—C3—C4—C5	0.2 (4)	O4—C10—C11—O3	−113.6 (3)
C3—C4—C5—C6	−0.6 (4)	O2—C10—C11—O3	127.4 (3)
C3—C4—C5—N1	−179.6 (2)	C9—C10—C11—O3	8.0 (3)
C8—N1—C5—C6	16.7 (4)	O4—C10—C11—C12	61.1 (2)
C9—N1—C5—C6	−177.0 (2)	O2—C10—C11—C12	−57.9 (2)
C8—N1—C5—C4	−164.3 (2)	C9—C10—C11—C12	−177.25 (19)
C9—N1—C5—C4	1.9 (3)	C15—O6—C12—C11	95.7 (3)
C4—C5—C6—C7	0.2 (4)	C15—O6—C12—C13	−23.5 (3)
N1—C5—C6—C7	179.2 (2)	O3—C11—C12—O6	12.3 (4)
C3—C2—C7—C6	−1.0 (4)	C10—C11—C12—O6	−162.21 (18)
C1—C2—C7—C6	176.7 (3)	O3—C11—C12—C13	127.5 (3)
C5—C6—C7—C2	0.6 (4)	C10—C11—C12—C13	−47.0 (3)
C5—N1—C8—O1	−7.5 (4)	C15—O5—C13—C14	−160.6 (2)
C9—N1—C8—O1	−175.0 (3)	C15—O5—C13—C12	−37.3 (2)
C5—N1—C8—O2	173.46 (19)	O6—C12—C13—O5	36.9 (2)
C9—N1—C8—O2	5.9 (3)	C11—C12—C13—O5	−83.8 (2)
C10—O2—C8—O1	−172.9 (2)	O6—C12—C13—C14	157.0 (2)
C10—O2—C8—N1	6.2 (3)	C11—C12—C13—C14	36.3 (3)
C8—N1—C9—C10	−14.5 (2)	C10—O4—C14—C13	56.3 (3)
C5—N1—C9—C10	177.48 (19)	O5—C13—C14—O4	73.7 (3)
C14—O4—C10—O2	53.3 (3)	C12—C13—C14—O4	−40.2 (3)
C14—O4—C10—C9	168.83 (19)	C13—O5—C15—O6	24.2 (3)
C14—O4—C10—C11	−64.6 (2)	C13—O5—C15—C17	142.0 (2)
C8—O2—C10—O4	102.5 (2)	C13—O5—C15—C16	−94.1 (3)
C8—O2—C10—C9	−15.2 (3)	C12—O6—C15—O5	0.8 (3)
C8—O2—C10—C11	−141.4 (2)	C12—O6—C15—C17	−115.8 (3)
N1—C9—C10—O4	−101.3 (2)	C12—O6—C15—C16	120.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···O1ⁱ	0.97	2.54	3.093 (3)	116
C14—H14B···O4ⁱⁱ	0.97	2.55	3.426 (3)	151

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₉NO₆
M_r	333.33
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	296
a, b, c (Å)	11.1268 (8), 6.3163 (5), 11.8697 (8)
β (°)	94.084 (1)
V (Å³)	832.09 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.18 × 0.15 × 0.13

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.982, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	8821, 1795, 1389
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.075, 1.06
No. of reflections	1795
No. of parameters	220
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.10, −0.13

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···O1ⁱ	0.97	2.54	3.093 (3)	116
C14—H14B···O4ⁱⁱ	0.97	2.55	3.426 (3)	151

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

Acknowledgements

This work was supported by the Basic Research Foundation for Natural Science of Henan University.

References

Bruker (2001). SAINT-Plus and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Denmark, S. E. & Wu, Z. (1999). Synlett, pp. 847–859. Google Scholar
Sheldrick, G. M. (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shi, Y. (2004). Acc. Chem. Res. 37, 488–496. Web of Science CrossRef PubMed CAS Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yang, D. (2004). Acc. Chem. Res. 37, 497–505. Web of Science CrossRef PubMed CAS Google Scholar
Zhao, M.-X., Goeddel, D., Li, K. & Shi, Y. (2006). Tetrahedron, 62, 8064–8068. Web of Science CrossRef CAS Google Scholar

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Volume 64| Part 11| November 2008| Page o2181

doi:10.1107/S1600536808034259

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

8,9-Iso­propyl­idenedi­­oxy-3-p-tolyl-1,6-dioxa-3-aza­spiro­[4.5]decane-2,10-dione

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References

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8,9-Isopropylidenedioxy-3-p-tolyl-1,6-dioxa-3-azaspiro[4.5]decane-2,10-dione