8,9-Isopropyl-idenedi-oxy-3-p-tolyl-1,6-dioxa-3-aza-spiro-[4.5]decane-2,10-dione.

In the title compound, C(17)H(19)NO(6), which may serve as a ketone catalyst for the asymmetric epoxidation of olefins, the crystal packing is consolidated by C-H⋯O inter-actions.

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 = 333.33

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.075

S = 1.06

1795 reflections

220 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.10 e Å−3

Δρmin = −0.13 e Å−3

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C17H19NO6	F(000) = 352
Mr = 333.33	Dx = 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

Bruker SMART CCD diffractometer	1795 independent reflections
Radiation source: fine-focus sealed tube	1389 reflections with I > 2σ(I)
graphite	Rint = 0.028
ω scans	θmax = 26.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −13→13
Tmin = 0.982, Tmax = 0.987	k = −7→7
8821 measured reflections	l = −14→14

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(Fo2) + (0.0303P)2 + 0.0894P] where P = (Fo2 + 2Fc2)/3
1795 reflections	(Δ/σ)max < 0.001
220 parameters	Δρmax = 0.10 e Å−3
1 restraint	Δρmin = −0.13 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) .