4-(3,5-Dioxo-10-oxa-4-aza-tricyclo-[5.2.1.0]decan-4-yl)-10-oxa-4-aza-tricyclo-[5.2.1.0]decane-3,5-dione.

In the title compound, C(16)H(16)N(2)O(6), the dihedral angle between the two pyrrolidine rings is 79.38 (14)°.

Related literature

Norcantharidin [systematic name: 7-oxabicyclo­(2.2.1)heptane-2,3-dicarb­oxy­lic anhydride] and its derivatives are of significant inter­est as serine/threonine protein phosphatase 1 and 2A inhibitors, see: Hill et al. (2008 ▶). For related structures, see: Li et al. (2011 ▶); Zhu & Lin (2009 ▶).

Experimental

Crystal data

C16H16N2O6

M = 332.31

Orthorhombic,

a = 10.2342 (6) Å

b = 10.5673 (6) Å

c = 27.3485 (17) Å

V = 2957.7 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.12 mm−1

T = 296 K

0.14 × 0.09 × 0.08 mm

Data collection

Bruker P4 diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.987, T max = 0.991

43071 measured reflections

3423 independent reflections

1581 reflections with I > 2σ(I)

R int = 0.163

Refinement

R[F 2 > 2σ(F 2)] = 0.083

wR(F 2) = 0.224

S = 1.07

3423 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812000542/ff2050sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812000542/ff2050Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812000542/ff2050Isup3.cml

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

C16H16N2O6	F(000) = 1392
Mr = 332.31	Dx = 1.493 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2007 reflections
a = 10.2342 (6) Å	θ = 1.5–27.6°
b = 10.5673 (6) Å	µ = 0.12 mm−1
c = 27.3485 (17) Å	T = 296 K
V = 2957.7 (3) Å3	Block, colourless
Z = 8	0.14 × 0.09 × 0.08 mm

Bruker P4 diffractometer	3423 independent reflections
Radiation source: fine-focus sealed tube	1581 reflections with I > 2σ(I)
graphite	Rint = 0.163
ω scans	θmax = 27.6°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.987, Tmax = 0.991	k = −13→13
43071 measured reflections	l = −35→35

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)] = 0.083	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.224	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0862P)2 + 1.8201P] where P = (Fo2 + 2Fc2)/3
3423 reflections	(Δ/σ)max = 0.002
217 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.21 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
O4	0.4418 (3)	−0.1479 (3)	0.03560 (11)	0.0595 (8)
O1	0.5405 (3)	0.4020 (3)	0.13629 (11)	0.0643 (9)
N1	0.5287 (3)	0.0942 (3)	0.15182 (13)	0.0517 (9)
O2	0.3401 (3)	0.1174 (3)	0.10792 (12)	0.0658 (9)
O3	0.7107 (3)	0.1261 (3)	0.19883 (14)	0.0784 (11)
O5	0.6972 (3)	0.0800 (3)	0.07064 (12)	0.0701 (10)
C16	0.5130 (4)	−0.1318 (4)	0.14002 (15)	0.0484 (10)
C11	0.6499 (4)	−0.1471 (3)	0.06726 (14)	0.0486 (10)
H11A	0.7384	−0.1821	0.0654	0.058*
N2	0.5691 (3)	−0.0145 (3)	0.12856 (13)	0.0496 (9)
C12	0.5594 (4)	−0.2230 (3)	0.10115 (14)	0.0446 (10)
H12A	0.6021	−0.2979	0.1149	0.054*
O6	0.4401 (3)	−0.1492 (3)	0.17385 (11)	0.0654 (9)
C7	0.4108 (4)	0.1543 (4)	0.13968 (16)	0.0498 (10)
C1	0.5826 (4)	0.3963 (4)	0.18576 (17)	0.0557 (12)
H1A	0.6776	0.4021	0.1896	0.067*
C8	0.6043 (4)	0.1584 (4)	0.18598 (16)	0.0502 (11)
C10	0.4465 (4)	−0.2567 (4)	0.06668 (16)	0.0542 (11)
H10A	0.3640	−0.2742	0.0836	0.065*
C15	0.6466 (4)	−0.0144 (4)	0.08651 (16)	0.0510 (11)
C3	0.5256 (4)	0.2710 (4)	0.20309 (16)	0.0491 (10)
H3A	0.5105	0.2698	0.2385	0.059*
C2	0.4016 (5)	0.3919 (4)	0.14670 (18)	0.0622 (13)
H2A	0.3459	0.3956	0.1176	0.075*
C14	0.4899 (5)	−0.3623 (4)	0.03254 (17)	0.0622 (12)
H14A	0.4165	−0.3986	0.0150	0.075*
H14B	0.5357	−0.4286	0.0501	0.075*
C9	0.5756 (4)	−0.1560 (4)	0.01894 (16)	0.0545 (11)
H9A	0.5995	−0.0901	−0.0046	0.065*
C13	0.5819 (5)	−0.2898 (4)	−0.00196 (16)	0.0623 (13)
H13A	0.6700	−0.3235	−0.0007	0.075*
H13B	0.5507	−0.2923	−0.0354	0.075*
C4	0.3968 (4)	0.2652 (4)	0.17362 (16)	0.0500 (11)
H4A	0.3199	0.2579	0.1948	0.060*
C6	0.3774 (5)	0.4990 (4)	0.18326 (18)	0.0640 (13)
H6A	0.3051	0.4795	0.2049	0.077*
H6B	0.3602	0.5785	0.1667	0.077*
C5	0.5080 (5)	0.5027 (4)	0.21108 (18)	0.0626 (13)
H5A	0.5517	0.5835	0.2071	0.075*
H5B	0.4961	0.4856	0.2456	0.075*

	U11	U22	U33	U12	U13	U23
O4	0.057 (2)	0.0543 (18)	0.0669 (19)	0.0109 (15)	−0.0062 (16)	−0.0045 (15)
O1	0.080 (3)	0.0474 (17)	0.065 (2)	−0.0046 (15)	0.0149 (18)	0.0010 (15)
N1	0.056 (2)	0.0350 (18)	0.064 (2)	0.0030 (16)	−0.0021 (18)	−0.0112 (16)
O2	0.058 (2)	0.0620 (19)	0.077 (2)	0.0033 (16)	−0.0110 (18)	−0.0143 (17)
O3	0.066 (2)	0.061 (2)	0.108 (3)	0.0160 (17)	−0.025 (2)	−0.0178 (19)
O5	0.074 (2)	0.0484 (17)	0.088 (2)	−0.0161 (16)	0.0124 (18)	0.0048 (17)
C16	0.057 (3)	0.041 (2)	0.046 (2)	0.004 (2)	0.002 (2)	0.001 (2)
C11	0.057 (3)	0.036 (2)	0.053 (2)	0.0058 (19)	0.004 (2)	0.0009 (18)
N2	0.056 (2)	0.0322 (17)	0.060 (2)	0.0004 (16)	0.0071 (19)	−0.0058 (16)
C12	0.050 (3)	0.0285 (19)	0.055 (2)	0.0028 (18)	0.000 (2)	0.0018 (17)
O6	0.085 (2)	0.0537 (18)	0.0576 (18)	−0.0048 (17)	0.0187 (18)	−0.0052 (15)
C7	0.047 (3)	0.042 (2)	0.061 (3)	−0.003 (2)	0.001 (2)	0.001 (2)
C1	0.051 (3)	0.039 (2)	0.078 (3)	−0.0008 (19)	−0.002 (2)	−0.003 (2)
C8	0.046 (3)	0.039 (2)	0.065 (3)	0.001 (2)	−0.005 (2)	0.000 (2)
C10	0.056 (3)	0.045 (2)	0.062 (3)	−0.005 (2)	0.005 (2)	−0.003 (2)
C15	0.047 (3)	0.043 (2)	0.063 (3)	−0.001 (2)	−0.002 (2)	0.003 (2)
C3	0.057 (3)	0.037 (2)	0.054 (2)	−0.0003 (19)	−0.001 (2)	−0.0046 (19)
C2	0.070 (3)	0.046 (2)	0.070 (3)	0.006 (2)	−0.010 (3)	0.002 (2)
C14	0.079 (3)	0.042 (2)	0.065 (3)	0.000 (2)	−0.003 (3)	−0.012 (2)
C9	0.062 (3)	0.048 (2)	0.053 (2)	0.007 (2)	0.002 (2)	0.005 (2)
C13	0.075 (3)	0.060 (3)	0.052 (3)	0.013 (2)	0.000 (2)	−0.009 (2)
C4	0.042 (2)	0.043 (2)	0.065 (3)	0.0022 (19)	0.001 (2)	−0.002 (2)
C6	0.064 (3)	0.041 (2)	0.087 (3)	0.010 (2)	−0.005 (3)	−0.004 (2)
C5	0.075 (3)	0.038 (2)	0.075 (3)	0.001 (2)	0.001 (3)	−0.011 (2)

O4—C10	1.431 (5)	C1—H1A	0.9800
O4—C9	1.446 (5)	C8—C3	1.511 (6)
O1—C1	1.421 (5)	C10—C14	1.520 (6)
O1—C2	1.454 (6)	C10—H10A	0.9800
N1—N2	1.376 (4)	C3—C4	1.547 (6)
N1—C8	1.390 (5)	C3—H3A	0.9800
N1—C7	1.404 (5)	C2—C4	1.529 (6)
O2—C7	1.196 (5)	C2—C6	1.530 (6)
O3—C8	1.194 (5)	C2—H2A	0.9800
O5—C15	1.205 (5)	C14—C13	1.537 (6)
C16—O6	1.203 (5)	C14—H14A	0.9700
C16—N2	1.402 (5)	C14—H14B	0.9700
C16—C12	1.511 (5)	C9—C13	1.526 (6)
C11—C15	1.498 (6)	C9—H9A	0.9800
C11—C9	1.527 (6)	C13—H13A	0.9700
C11—C12	1.536 (5)	C13—H13B	0.9700
C11—H11A	0.9800	C4—H4A	0.9800
N2—C15	1.397 (5)	C6—C5	1.539 (7)
C12—C10	1.533 (6)	C6—H6A	0.9700
C12—H12A	0.9800	C6—H6B	0.9700
C7—C4	1.502 (6)	C5—H5A	0.9700
C1—C3	1.523 (6)	C5—H5B	0.9700
C1—C5	1.525 (6)
C10—O4—C9	96.2 (3)	C1—C3—C4	101.5 (3)
C1—O1—C2	96.2 (3)	C8—C3—H3A	112.3
N2—N1—C8	123.4 (3)	C1—C3—H3A	112.3
N2—N1—C7	121.8 (3)	C4—C3—H3A	112.3
C8—N1—C7	114.6 (3)	O1—C2—C4	101.0 (3)
O6—C16—N2	124.1 (4)	O1—C2—C6	103.4 (4)
O6—C16—C12	129.7 (4)	C4—C2—C6	109.1 (4)
N2—C16—C12	106.1 (3)	O1—C2—H2A	114.0
C15—C11—C9	110.5 (3)	C4—C2—H2A	114.0
C15—C11—C12	105.3 (3)	C6—C2—H2A	114.0
C9—C11—C12	101.0 (3)	C10—C14—C13	101.0 (3)
C15—C11—H11A	113.1	C10—C14—H14A	111.6
C9—C11—H11A	113.1	C13—C14—H14A	111.6
C12—C11—H11A	113.1	C10—C14—H14B	111.6
N1—N2—C15	123.4 (3)	C13—C14—H14B	111.6
N1—N2—C16	120.8 (3)	H14A—C14—H14B	109.4
C15—N2—C16	114.6 (3)	O4—C9—C13	102.3 (3)
C16—C12—C10	110.1 (3)	O4—C9—C11	101.2 (3)
C16—C12—C11	106.3 (3)	C13—C9—C11	111.1 (3)
C10—C12—C11	101.8 (3)	O4—C9—H9A	113.7
C16—C12—H12A	112.6	C13—C9—H9A	113.7
C10—C12—H12A	112.6	C11—C9—H9A	113.7
C11—C12—H12A	112.6	C9—C13—C14	101.9 (3)
O2—C7—N1	123.0 (4)	C9—C13—H13A	111.4
O2—C7—C4	130.2 (4)	C14—C13—H13A	111.4
N1—C7—C4	106.8 (4)	C9—C13—H13B	111.4
O1—C1—C3	102.5 (3)	C14—C13—H13B	111.4
O1—C1—C5	104.4 (4)	H13A—C13—H13B	109.3
C3—C1—C5	107.9 (4)	C7—C4—C2	112.5 (4)
O1—C1—H1A	113.7	C7—C4—C3	105.7 (3)
C3—C1—H1A	113.7	C2—C4—C3	100.9 (3)
C5—C1—H1A	113.7	C7—C4—H4A	112.3
O3—C8—N1	124.5 (4)	C2—C4—H4A	112.3
O3—C8—C3	128.3 (4)	C3—C4—H4A	112.3
N1—C8—C3	107.2 (4)	C2—C6—C5	101.6 (4)
O4—C10—C14	103.6 (3)	C2—C6—H6A	111.4
O4—C10—C12	101.7 (3)	C5—C6—H6A	111.4
C14—C10—C12	109.1 (4)	C2—C6—H6B	111.4
O4—C10—H10A	113.8	C5—C6—H6B	111.4
C14—C10—H10A	113.8	H6A—C6—H6B	109.3
C12—C10—H10A	113.8	C1—C5—C6	101.1 (4)
O5—C15—N2	122.7 (4)	C1—C5—H5A	111.6
O5—C15—C11	129.7 (4)	C6—C5—H5A	111.6
N2—C15—C11	107.5 (3)	C1—C5—H5B	111.6
C8—C3—C1	112.6 (4)	C6—C5—H5B	111.6
C8—C3—C4	105.2 (3)	H5A—C5—H5B	109.4