exo-4-[(1H-Benzimidazol-2-yl)meth­yl]-10-oxa-4-aza­tricyclo­[5.2.1.02,6]decane-3,5-dione

Li, S.-K.; Zhang, F.; Lv, T.-X.; Lin, Q.-Y.

doi:10.1107/S1600536811026602

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o1974

doi:10.1107/S1600536811026602

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exo-4-[(1H-Benzimidazol-2-yl)methyl]-10-oxa-4-azatricyclo[5.2.1.0^2,6]decane-3,5-dione

Shi-Kun Li,^a,^b Fan Zhang,^a,^b Tian-Xi Lv ^b and Qiu-Yue Lin ^a,^b ^*

^aZhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces, Institute of Physical Chemistry, Zhejiang Normal University, Jinhua 321004, Zhejiang, People's Republic of China, and ^bCollege of Chemistry and Life Science, Zhejiang Normal University, Jinhua 321004, Zhejiang, People's Republic of China
^*Correspondence e-mail: sky51@zjnu.cn

(Received 29 April 2011; accepted 4 July 2011; online 9 July 2011)

In the title compound, C₁₆H₁₅N₃O₃, the dihedral angle between the approximately planar benzimidazolyl group (r.m.s. deviation = 0.010 Å) and the pyrrolidine ring is 78.20 (6)°. The C—C—N bond angle of the bridging CH₂ group is 112.14 (16)°. In the crystal, molecules are linked via N—H⋯N hydrogen bonds, forming infinite chains parallel to [101] and [10 $[\overline{1}]$ ].

Related literature

For the bioactivity of norcantharidin (systematic name 4,10-dioxatricyclo[5.2.1.0^2,6]decane-3,5-dione), see: Wang (1989 ). For the use of norcantharidin in synthesis, see: Hill et al. (2007 ). For a related structure, see: Zhu & Lin (2009 ).

Experimental

Crystal data

C₁₆H₁₅N₃O₃
M_r = 297.31
Orthorhombic, F d d 2
a = 17.4294 (2) Å
b = 48.2746 (6) Å
c = 6.7947 (1) Å
V = 5717.04 (13) Å³
Z = 16
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.24 × 0.17 × 0.10 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.981, T_max = 0.990
22741 measured reflections
2159 independent reflections
1690 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.087
S = 1.04
2159 reflections
199 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.10 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N2ⁱ	0.86	1.97	2.827 (2)	175
Symmetry code: (i) $[x+{\script{1\over 4}}, -y+{\script{1\over 4}}, z+{\script{1\over 4}}]$ .

Data collection: APEX2 (Bruker, 2006 ); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811026602/qk2008sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811026602/qk2008Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811026602/qk2008Isup3.cml

checkCIF report

Comment top

Norcantharidin is an important compound that has a variety of bioactivities, such as protein kinase inhibition and antitumor activity (Wang, 1989). As a contribution to structure-activity studies in this field, the title compound, (I), a norcantharidin imide (Hill et al., 2007), was synthesized and investigated by X-ray crystallography. A related norcantharidin imide was reported by Zhu & Lin (2009).

X-ray crystallography confirmed the anticipated molecular structure and the atom connectivity for the title compound, as illustrated in Fig. 1. The norcantharidin imide and the benzimidazole moiety of (I) are rigid and feature usual bond lengths and angles. The dihedral angle between the flat benzimidazolyl group (C9—C15,N1,N2) and the pyrrolidine ring (C1,C2,C7,C8,N3) is 78.20 (6)°. The bond angle of the bridging CH₂ group is C15—C16—N3 = 112.1 (2)°. In the crystal structure the molecules are linked via the hydrogen bond N1—H1A···N2ⁱ, N1···N2ⁱ = 2.827 (2) Å ((i): x+1/4, -y+1/4, z+1/4), to form infinite hydrogen bonded chains parallel to [101] and [101].

Related literature top

For the bioactivity of norcantharidin (systematic name 4,10-dioxatricyclo[5.2.1.0^2,6]decane-3,5-dione), see: Wang (1989). For the use of norcantharidin in synthesis, see: Hill et al. (2007). For a related structure, see: Zhu & Lin (2009).

Experimental top

A mixture of 0.5 mmol norcantharidin, 0.5 mmol 2-(aminomethyl)benzimidazole, 0.5 mmol cadmium acetate as a promoter, and 10 mL distilled water was sealed in a 25 mL Teflon-lined stainless vessel and heated at 433 K for 3 d, then cooled slowly to room temperature. The solution was filtered and gave then block-like transparent crystals.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. A view of the molecule of (I) showing the atom-labelling scheme with displacement ellipsoids drawn at 30% probability.

exo-8-[(1H-Benzimidazol-2-yl)methyl]-10-oxa-8- azatricyclo[4.3.0.1^2,5]decane-7,9-dione top

Crystal data top

C₁₆H₁₅N₃O₃	F(000) = 2496
M_r = 297.31	D_x = 1.382 Mg m⁻³
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 5637 reflections
a = 17.4294 (2) Å	θ = 2.5–29.8°
b = 48.2746 (6) Å	µ = 0.10 mm⁻¹
c = 6.7947 (1) Å	T = 296 K
V = 5717.04 (13) Å³	Block, colourless
Z = 16	0.24 × 0.17 × 0.10 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	2159 independent reflections
Radiation source: fine-focus sealed tube	1690 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ω scans	θ_max = 29.8°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −24→24
T_min = 0.981, T_max = 0.990	k = −67→66
22741 measured reflections	l = −9→8

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.035	H-atom parameters constrained
wR(F²) = 0.087	w = 1/[σ²(F_o²) + (0.0448P)² + 1.1097P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2159 reflections	Δρ_max = 0.10 e Å⁻³
199 parameters	Δρ_min = −0.17 e Å⁻³
1 restraint	Absolute structure: 1753 Friedel pairs were merged
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₆H₁₅N₃O₃	V = 5717.04 (13) Å³
M_r = 297.31	Z = 16
Orthorhombic, Fdd2	Mo Kα radiation
a = 17.4294 (2) Å	µ = 0.10 mm⁻¹
b = 48.2746 (6) Å	T = 296 K
c = 6.7947 (1) Å	0.24 × 0.17 × 0.10 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	2159 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1690 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.990	R_int = 0.038
22741 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	1 restraint
wR(F²) = 0.087	H-atom parameters constrained
S = 1.04	Δρ_max = 0.10 e Å⁻³
2159 reflections	Δρ_min = −0.17 e Å⁻³
199 parameters	Absolute structure: 1753 Friedel pairs were merged

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
N2	−0.06276 (8)	0.10833 (3)	0.2792 (3)	0.0454 (4)
N1	0.04528 (8)	0.11596 (3)	0.4450 (3)	0.0428 (4)
H1A	0.0893	0.1229	0.4740	0.051*
N3	−0.02809 (8)	0.16452 (3)	0.1037 (3)	0.0431 (4)
O2	−0.07386 (9)	0.14915 (3)	−0.1930 (3)	0.0629 (4)
O1	−0.00312 (11)	0.18963 (4)	0.3811 (3)	0.0765 (5)
O3	−0.02560 (7)	0.22474 (3)	−0.0973 (2)	0.0556 (4)
C1	−0.07375 (10)	0.16595 (3)	−0.0624 (3)	0.0439 (4)
C2	−0.12089 (10)	0.19215 (3)	−0.0513 (3)	0.0431 (4)
H2B	−0.1761	0.1887	−0.0634	0.052*
C3	−0.09207 (12)	0.21403 (4)	−0.1970 (3)	0.0527 (5)
H3A	−0.0813	0.2068	−0.3288	0.063*
C4	−0.14630 (14)	0.23883 (4)	−0.1956 (5)	0.0713 (7)
H4A	−0.1995	0.2330	−0.2016	0.086*
H4B	−0.1357	0.2513	−0.3041	0.086*
C5	−0.12741 (14)	0.25219 (4)	0.0024 (4)	0.0700 (7)
H5A	−0.1088	0.2710	−0.0139	0.084*
H5B	−0.1716	0.2523	0.0892	0.084*
C6	−0.06469 (12)	0.23307 (4)	0.0784 (4)	0.0552 (5)
H6A	−0.0311	0.2417	0.1763	0.066*
C7	−0.09930 (11)	0.20533 (4)	0.1463 (3)	0.0464 (5)
H7A	−0.1434	0.2077	0.2341	0.056*
C8	−0.03878 (12)	0.18644 (4)	0.2306 (3)	0.0492 (5)
C16	0.02831 (10)	0.14281 (4)	0.1375 (4)	0.0519 (5)
H16A	0.0760	0.1511	0.1814	0.062*
H16B	0.0384	0.1333	0.0145	0.062*
C15	0.00198 (10)	0.12236 (3)	0.2871 (3)	0.0410 (4)
C9	−0.06167 (9)	0.09153 (3)	0.4452 (3)	0.0391 (4)
C10	−0.11496 (11)	0.07221 (4)	0.5106 (3)	0.0488 (5)
H10A	−0.1597	0.0687	0.4402	0.059*
C11	−0.09925 (12)	0.05847 (4)	0.6828 (4)	0.0571 (5)
H11A	−0.1339	0.0453	0.7288	0.068*
C12	−0.03280 (13)	0.06372 (5)	0.7903 (4)	0.0600 (6)
H12A	−0.0247	0.0543	0.9078	0.072*
C13	0.02144 (11)	0.08263 (4)	0.7270 (3)	0.0526 (5)
H13A	0.0660	0.0861	0.7984	0.063*
C14	0.00597 (10)	0.09617 (3)	0.5518 (3)	0.0395 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N2	0.0332 (7)	0.0520 (8)	0.0510 (10)	−0.0018 (6)	−0.0111 (7)	0.0068 (8)
N1	0.0308 (7)	0.0445 (7)	0.0532 (10)	−0.0010 (6)	−0.0124 (8)	−0.0003 (7)
N3	0.0394 (8)	0.0408 (7)	0.0490 (10)	0.0022 (6)	−0.0058 (7)	0.0065 (7)
O2	0.0768 (10)	0.0467 (7)	0.0652 (11)	0.0086 (7)	−0.0172 (9)	−0.0142 (8)
O1	0.0876 (11)	0.0950 (13)	0.0468 (11)	0.0081 (9)	−0.0214 (10)	−0.0072 (9)
O3	0.0472 (7)	0.0489 (7)	0.0708 (11)	−0.0026 (6)	0.0051 (8)	0.0100 (7)
C1	0.0451 (9)	0.0351 (8)	0.0514 (12)	−0.0021 (7)	−0.0074 (9)	0.0015 (8)
C2	0.0380 (9)	0.0387 (8)	0.0525 (11)	0.0014 (7)	−0.0062 (9)	−0.0002 (8)
C3	0.0624 (12)	0.0469 (10)	0.0489 (13)	0.0087 (9)	−0.0070 (11)	0.0047 (9)
C4	0.0740 (15)	0.0457 (10)	0.094 (2)	0.0098 (10)	−0.0194 (15)	0.0099 (13)
C5	0.0703 (13)	0.0407 (9)	0.099 (2)	0.0100 (10)	0.0017 (15)	−0.0043 (12)
C6	0.0576 (12)	0.0427 (9)	0.0654 (15)	−0.0041 (8)	−0.0085 (11)	−0.0086 (10)
C7	0.0447 (10)	0.0481 (9)	0.0466 (12)	0.0029 (8)	0.0035 (9)	−0.0034 (9)
C8	0.0493 (11)	0.0568 (11)	0.0414 (12)	−0.0011 (9)	−0.0015 (10)	0.0022 (9)
C16	0.0386 (9)	0.0511 (10)	0.0660 (15)	0.0073 (8)	−0.0002 (10)	0.0147 (10)
C15	0.0324 (8)	0.0416 (8)	0.0490 (12)	0.0040 (7)	−0.0080 (8)	0.0041 (8)
C9	0.0334 (8)	0.0393 (8)	0.0444 (11)	0.0033 (6)	−0.0079 (8)	−0.0022 (8)
C10	0.0394 (9)	0.0502 (10)	0.0570 (14)	−0.0041 (8)	−0.0060 (9)	−0.0017 (9)
C11	0.0535 (11)	0.0506 (10)	0.0671 (15)	−0.0001 (8)	0.0027 (12)	0.0114 (11)
C12	0.0610 (12)	0.0633 (12)	0.0558 (14)	0.0089 (10)	−0.0030 (11)	0.0175 (11)
C13	0.0470 (11)	0.0628 (11)	0.0480 (12)	0.0076 (9)	−0.0156 (10)	0.0025 (10)
C14	0.0333 (8)	0.0388 (8)	0.0463 (12)	0.0042 (7)	−0.0079 (8)	−0.0021 (8)

Geometric parameters (Å, º) top

N2—C15	1.317 (2)	C5—C6	1.521 (3)
N2—C9	1.389 (2)	C5—H5A	0.9700
N1—C15	1.348 (3)	C5—H5B	0.9700
N1—C14	1.381 (2)	C6—C7	1.540 (3)
N1—H1A	0.8600	C6—H6A	0.9800
N3—C8	1.378 (3)	C7—C8	1.507 (3)
N3—C1	1.383 (3)	C7—H7A	0.9800
N3—C16	1.455 (2)	C16—C15	1.490 (3)
O2—C1	1.202 (2)	C16—H16A	0.9700
O1—C8	1.206 (3)	C16—H16B	0.9700
O3—C6	1.432 (3)	C9—C10	1.389 (3)
O3—C3	1.438 (3)	C9—C14	1.402 (2)
C1—C2	1.510 (2)	C10—C11	1.373 (3)
C2—C3	1.532 (3)	C10—H10A	0.9300
C2—C7	1.533 (3)	C11—C12	1.393 (3)
C2—H2B	0.9800	C11—H11A	0.9300
C3—C4	1.525 (3)	C12—C13	1.383 (3)
C3—H3A	0.9800	C12—H12A	0.9300
C4—C5	1.528 (4)	C13—C14	1.385 (3)
C4—H4A	0.9700	C13—H13A	0.9300
C4—H4B	0.9700

C15—N2—C9	104.80 (15)	C5—C6—H6A	113.7
C15—N1—C14	107.39 (14)	C7—C6—H6A	113.7
C15—N1—H1A	126.3	C8—C7—C2	104.70 (15)
C14—N1—H1A	126.3	C8—C7—C6	111.46 (16)
C8—N3—C1	113.23 (15)	C2—C7—C6	101.23 (17)
C8—N3—C16	123.08 (17)	C8—C7—H7A	112.9
C1—N3—C16	123.63 (17)	C2—C7—H7A	112.9
C6—O3—C3	96.35 (15)	C6—C7—H7A	112.9
O2—C1—N3	124.71 (16)	O1—C8—N3	124.0 (2)
O2—C1—C2	126.96 (19)	O1—C8—C7	127.3 (2)
N3—C1—C2	108.33 (16)	N3—C8—C7	108.75 (17)
C1—C2—C3	111.50 (17)	N3—C16—C15	112.14 (16)
C1—C2—C7	104.94 (16)	N3—C16—H16A	109.2
C3—C2—C7	101.50 (14)	C15—C16—H16A	109.2
C1—C2—H2B	112.7	N3—C16—H16B	109.2
C3—C2—H2B	112.7	C15—C16—H16B	109.2
C7—C2—H2B	112.7	H16A—C16—H16B	107.9
O3—C3—C4	102.38 (16)	N2—C15—N1	113.22 (17)
O3—C3—C2	101.96 (16)	N2—C15—C16	125.23 (18)
C4—C3—C2	109.49 (19)	N1—C15—C16	121.52 (16)
O3—C3—H3A	113.9	C10—C9—N2	129.97 (16)
C4—C3—H3A	113.9	C10—C9—C14	120.28 (17)
C2—C3—H3A	113.9	N2—C9—C14	109.74 (15)
C3—C4—C5	101.72 (19)	C11—C10—C9	117.63 (18)
C3—C4—H4A	111.4	C11—C10—H10A	121.2
C5—C4—H4A	111.4	C9—C10—H10A	121.2
C3—C4—H4B	111.4	C10—C11—C12	121.7 (2)
C5—C4—H4B	111.4	C10—C11—H11A	119.2
H4A—C4—H4B	109.3	C12—C11—H11A	119.2
C6—C5—C4	101.42 (18)	C13—C12—C11	121.7 (2)
C6—C5—H5A	111.5	C13—C12—H12A	119.1
C4—C5—H5A	111.5	C11—C12—H12A	119.1
C6—C5—H5B	111.5	C12—C13—C14	116.48 (19)
C4—C5—H5B	111.5	C12—C13—H13A	121.8
H5A—C5—H5B	109.3	C14—C13—H13A	121.8
O3—C6—C5	103.2 (2)	N1—C14—C13	132.96 (17)
O3—C6—C7	101.06 (15)	N1—C14—C9	104.84 (16)
C5—C6—C7	110.35 (16)	C13—C14—C9	122.19 (18)
O3—C6—H6A	113.7

C8—N3—C1—O2	179.8 (2)	C16—N3—C8—O1	−0.5 (3)
C16—N3—C1—O2	2.6 (3)	C1—N3—C8—C7	0.7 (2)
C8—N3—C1—C2	0.9 (2)	C16—N3—C8—C7	177.93 (16)
C16—N3—C1—C2	−176.28 (16)	C2—C7—C8—O1	176.4 (2)
O2—C1—C2—C3	−71.9 (2)	C6—C7—C8—O1	67.8 (3)
N3—C1—C2—C3	106.99 (19)	C2—C7—C8—N3	−2.0 (2)
O2—C1—C2—C7	179.06 (19)	C6—C7—C8—N3	−110.60 (19)
N3—C1—C2—C7	−2.10 (19)	C8—N3—C16—C15	77.7 (2)
C6—O3—C3—C4	55.9 (2)	C1—N3—C16—C15	−105.4 (2)
C6—O3—C3—C2	−57.41 (16)	C9—N2—C15—N1	0.1 (2)
C1—C2—C3—O3	−77.96 (19)	C9—N2—C15—C16	178.43 (18)
C7—C2—C3—O3	33.32 (17)	C14—N1—C15—N2	−0.4 (2)
C1—C2—C3—C4	174.13 (18)	C14—N1—C15—C16	−178.74 (17)
C7—C2—C3—C4	−74.6 (2)	N3—C16—C15—N2	55.2 (3)
O3—C3—C4—C5	−35.0 (2)	N3—C16—C15—N1	−126.70 (19)
C2—C3—C4—C5	72.7 (2)	C15—N2—C9—C10	−179.28 (19)
C3—C4—C5—C6	1.0 (2)	C15—N2—C9—C14	0.14 (19)
C3—O3—C6—C5	−55.61 (16)	N2—C9—C10—C11	−179.60 (19)
C3—O3—C6—C7	58.61 (15)	C14—C9—C10—C11	1.0 (3)
C4—C5—C6—O3	33.5 (2)	C9—C10—C11—C12	0.6 (3)
C4—C5—C6—C7	−73.8 (2)	C10—C11—C12—C13	−1.3 (4)
C1—C2—C7—C8	2.40 (19)	C11—C12—C13—C14	0.4 (3)
C3—C2—C7—C8	−113.79 (16)	C15—N1—C14—C13	−178.2 (2)
C1—C2—C7—C6	118.36 (16)	C15—N1—C14—C9	0.44 (19)
C3—C2—C7—C6	2.16 (17)	C12—C13—C14—N1	179.8 (2)
O3—C6—C7—C8	73.7 (2)	C12—C13—C14—C9	1.3 (3)
C5—C6—C7—C8	−177.5 (2)	C10—C9—C14—N1	179.13 (16)
O3—C6—C7—C2	−37.14 (17)	N2—C9—C14—N1	−0.36 (19)
C5—C6—C7—C2	71.6 (2)	C10—C9—C14—C13	−2.0 (3)
C1—N3—C8—O1	−177.7 (2)	N2—C9—C14—C13	178.48 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N2ⁱ	0.86	1.97	2.827 (2)	175

Symmetry code: (i) x+1/4, −y+1/4, z+1/4.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₅N₃O₃
M_r	297.31
Crystal system, space group	Orthorhombic, Fdd2
Temperature (K)	296
a, b, c (Å)	17.4294 (2), 48.2746 (6), 6.7947 (1)
V (Å³)	5717.04 (13)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.24 × 0.17 × 0.10

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.981, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	22741, 2159, 1690
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.699

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.087, 1.04
No. of reflections	2159
No. of parameters	199
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.10, −0.17
Absolute structure	1753 Friedel pairs were merged

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N2ⁱ	0.86	1.97	2.827 (2)	175

Symmetry code: (i) x+1/4, −y+1/4, z+1/4.

Acknowledgements

The authors thank for the financial support from the Natural Science Foundation of Zhejiang Province, China (Grant No. Y407301).

References

Bruker (2006). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hill, T. A., Stewart, S. G., Ackland, S. P., Sauer, B., Gilbert, J., Ackland, S. P., Sakoff, J. A. & McCluskey, A. (2007). Bioorg. Med. Chem. 15, 6126–6134. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, G.-S. (1989). J. Ethnopharmacol. 26, 147–162. CrossRef CAS PubMed Web of Science Google Scholar
Zhu, W.-Z. & Lin, Q.-Y. (2009). Acta Cryst. E65, o287. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 67| Part 8| August 2011| Page o1974

doi:10.1107/S1600536811026602

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

exo-4-[(1H-Benzimidazol-2-yl)meth­yl]-10-oxa-4-aza­tri­cyclo­[5.2.1.02,6]decane-3,5-dione

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

exo-4-[(1H-Benzimidazol-2-yl)methyl]-10-oxa-4-azatricyclo[5.2.1.0^2,6]decane-3,5-dione