4-(2-Oxa-6-aza-spiro-[3.3]hept-6-yl)-benzo-nitrile.

In the title compound, C(12)H(12)N(2)O, the azetidine ring (r.m.s. deviation = 0.021 Å) and the oxetane ring (r.m.s. deviation = 0.014 Å) are nearly perpendicular to each other [dihedral angle = 89.7 (1)°]. The azetidine ring is twisted out of the plane of the benzene ring by 18.3 (1)°. In the crystal structure, mol-ecules are linked to form chains along the c axis by C-H⋯O hydrogen bonds.

Related literature

The title compound is a key inter­mediate to synthesize (pyrrolo[3,4-c]pyrazol-3-yl)benzamide derivatives. For the anti-tumor effect of these derivatives, see: Fancelli et al. (2005 ▶).

Experimental

Crystal data

C12H12N2O

M = 200.24

Monoclinic,

a = 9.484 (4) Å

b = 11.033 (4) Å

c = 10.419 (4) Å

β = 113.186 (5)°

V = 1002.2 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 113 K

0.60 × 0.60 × 0.27 mm

Data collection

Rigaku AFC10/Saturn 724-Plus diffractometer

7662 measured reflections

2234 independent reflections

1872 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.099

S = 1.00

2234 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.16 e Å−3

Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810012936/ci5062sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810012936/ci5062Isup2.hkl

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

C12H12N2O	F(000) = 424
Mr = 200.24	Dx = 1.327 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.484 (4) Å	Cell parameters from 2956 reflections
b = 11.033 (4) Å	θ = 3.1–27.5°
c = 10.419 (4) Å	µ = 0.09 mm−1
β = 113.186 (5)°	T = 113 K
V = 1002.2 (7) Å3	Prism, colourless
Z = 4	0.60 × 0.60 × 0.27 mm

Rigaku AFC10/Saturn 724-Plus diffractometer	1872 reflections with I > 2σ(I)
Radiation source: rotating anode	Rint = 0.029
graphite	θmax = 27.5°, θmin = 3.1°
Detector resolution: 28.5714 pixels mm-1	h = −12→12
φ and ω scans	k = −14→11
7662 measured reflections	l = −12→12
2234 independent reflections

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0456P)2 + 0.36P] where P = (Fo2 + 2Fc2)/3
2234 reflections	(Δ/σ)max = 0.001
136 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
O1	0.53098 (12)	0.21116 (9)	−0.00129 (10)	0.0272 (3)
N1	0.81838 (14)	0.46062 (12)	1.07793 (13)	0.0275 (3)
N2	0.58259 (13)	0.37004 (10)	0.38573 (11)	0.0186 (3)
C1	0.74599 (15)	0.47583 (12)	0.59326 (14)	0.0178 (3)
H1	0.7933	0.5192	0.5421	0.021*
C2	0.79050 (15)	0.49646 (12)	0.73352 (14)	0.0186 (3)
H2	0.8679	0.5547	0.7788	0.022*
C3	0.72270 (15)	0.43219 (12)	0.81086 (14)	0.0177 (3)
C4	0.60810 (15)	0.34638 (12)	0.74350 (14)	0.0183 (3)
H4	0.5624	0.3022	0.7954	0.022*
C5	0.56183 (15)	0.32601 (12)	0.60278 (14)	0.0178 (3)
H5	0.4835	0.2683	0.5577	0.021*
C6	0.62984 (14)	0.39026 (12)	0.52463 (13)	0.0165 (3)
C7	0.49702 (15)	0.26581 (12)	0.30534 (14)	0.0178 (3)
H7A	0.3842	0.2751	0.2702	0.021*
H7B	0.5303	0.1871	0.3534	0.021*
C8	0.56407 (14)	0.29329 (12)	0.19522 (14)	0.0167 (3)
C9	0.65782 (15)	0.39702 (12)	0.28976 (13)	0.0177 (3)
H9A	0.7699	0.3827	0.3302	0.021*
H9B	0.6331	0.4782	0.2461	0.021*
C10	0.45979 (16)	0.31151 (12)	0.04116 (14)	0.0204 (3)
H10A	0.3499	0.2979	0.0208	0.024*
H10B	0.4749	0.3907	0.0037	0.024*
C11	0.63751 (16)	0.19237 (13)	0.14221 (14)	0.0226 (3)
H11A	0.7455	0.2092	0.1575	0.027*
H11B	0.6281	0.1114	0.1790	0.027*
C12	0.77569 (15)	0.44870 (12)	0.95891 (15)	0.0202 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0353 (6)	0.0266 (6)	0.0202 (5)	0.0027 (5)	0.0113 (5)	−0.0041 (4)
N1	0.0257 (7)	0.0323 (7)	0.0231 (7)	−0.0015 (5)	0.0082 (5)	−0.0038 (6)
N2	0.0203 (6)	0.0187 (6)	0.0180 (6)	−0.0073 (4)	0.0086 (5)	−0.0027 (5)
C1	0.0179 (6)	0.0147 (6)	0.0217 (7)	−0.0007 (5)	0.0086 (5)	0.0028 (5)
C2	0.0156 (6)	0.0151 (6)	0.0223 (7)	0.0007 (5)	0.0043 (5)	−0.0017 (5)
C3	0.0165 (6)	0.0176 (6)	0.0177 (7)	0.0041 (5)	0.0054 (5)	−0.0004 (5)
C4	0.0177 (6)	0.0181 (6)	0.0212 (7)	0.0025 (5)	0.0098 (5)	0.0022 (5)
C5	0.0157 (6)	0.0163 (6)	0.0212 (7)	−0.0017 (5)	0.0069 (5)	−0.0012 (5)
C6	0.0151 (6)	0.0147 (6)	0.0188 (7)	0.0023 (5)	0.0058 (5)	0.0008 (5)
C7	0.0184 (6)	0.0157 (6)	0.0195 (7)	−0.0029 (5)	0.0076 (5)	−0.0014 (5)
C8	0.0161 (6)	0.0149 (6)	0.0193 (7)	0.0004 (5)	0.0071 (5)	0.0002 (5)
C9	0.0171 (6)	0.0186 (6)	0.0172 (6)	−0.0020 (5)	0.0065 (5)	0.0004 (5)
C10	0.0210 (7)	0.0184 (6)	0.0195 (7)	−0.0010 (5)	0.0057 (5)	−0.0002 (6)
C11	0.0257 (7)	0.0215 (7)	0.0227 (7)	0.0046 (6)	0.0117 (6)	0.0016 (6)
C12	0.0175 (6)	0.0195 (6)	0.0235 (8)	0.0024 (5)	0.0079 (5)	−0.0010 (6)

O1—C11	1.4525 (17)	C5—C6	1.4125 (19)
O1—C10	1.4534 (17)	C5—H5	0.95
N1—C12	1.1504 (18)	C7—C8	1.5451 (18)
N2—C6	1.3544 (17)	C7—H7A	0.99
N2—C7	1.4653 (17)	C7—H7B	0.99
N2—C9	1.4695 (17)	C8—C11	1.5274 (18)
C1—C2	1.3711 (19)	C8—C10	1.5314 (18)
C1—C6	1.4127 (18)	C8—C9	1.5431 (18)
C1—H1	0.95	C9—H9A	0.99
C2—C3	1.4049 (19)	C9—H9B	0.99
C2—H2	0.95	C10—H10A	0.99
C3—C4	1.4034 (19)	C10—H10B	0.99
C3—C12	1.4335 (19)	C11—H11A	0.99
C4—C5	1.3734 (19)	C11—H11B	0.99
C4—H4	0.95
C11—O1—C10	90.79 (9)	H7A—C7—H7B	111.1
C6—N2—C7	128.02 (11)	C11—C8—C10	85.12 (10)
C6—N2—C9	130.44 (11)	C11—C8—C9	122.78 (11)
C7—N2—C9	94.47 (10)	C10—C8—C9	122.94 (11)
C2—C1—C6	120.13 (12)	C11—C8—C7	120.34 (11)
C2—C1—H1	119.9	C10—C8—C7	121.30 (11)
C6—C1—H1	119.9	C9—C8—C7	88.49 (10)
C1—C2—C3	120.61 (12)	N2—C9—C8	88.40 (10)
C1—C2—H2	119.7	N2—C9—H9A	113.9
C3—C2—H2	119.7	C8—C9—H9A	113.9
C4—C3—C2	119.53 (12)	N2—C9—H9B	113.9
C4—C3—C12	119.89 (12)	C8—C9—H9B	113.9
C2—C3—C12	120.49 (12)	H9A—C9—H9B	111.1
C5—C4—C3	120.22 (12)	O1—C10—C8	91.91 (10)
C5—C4—H4	119.9	O1—C10—H10A	113.3
C3—C4—H4	119.9	C8—C10—H10A	113.3
C4—C5—C6	120.45 (12)	O1—C10—H10B	113.3
C4—C5—H5	119.8	C8—C10—H10B	113.3
C6—C5—H5	119.8	H10A—C10—H10B	110.6
N2—C6—C5	119.95 (12)	O1—C11—C8	92.11 (10)
N2—C6—C1	121.00 (12)	O1—C11—H11A	113.3
C5—C6—C1	119.05 (12)	C8—C11—H11A	113.3
N2—C7—C8	88.47 (10)	O1—C11—H11B	113.3
N2—C7—H7A	113.9	C8—C11—H11B	113.3
C8—C7—H7A	113.9	H11A—C11—H11B	110.6
N2—C7—H7B	113.9	N1—C12—C3	179.26 (15)
C8—C7—H7B	113.9
C6—C1—C2—C3	0.67 (19)	N2—C7—C8—C11	130.78 (12)
C1—C2—C3—C4	−0.17 (18)	N2—C7—C8—C10	−125.31 (12)
C1—C2—C3—C12	176.30 (12)	N2—C7—C8—C9	3.04 (9)
C2—C3—C4—C5	−0.45 (19)	C6—N2—C9—C8	154.66 (13)
C12—C3—C4—C5	−176.95 (12)	C7—N2—C9—C8	3.21 (10)
C3—C4—C5—C6	0.57 (19)	C11—C8—C9—N2	−128.76 (12)
C7—N2—C6—C5	−18.4 (2)	C10—C8—C9—N2	123.99 (12)
C9—N2—C6—C5	−161.23 (13)	C7—C8—C9—N2	−3.04 (9)
C7—N2—C6—C1	162.08 (12)	C11—O1—C10—C8	−2.22 (10)
C9—N2—C6—C1	19.3 (2)	C11—C8—C10—O1	2.12 (10)
C4—C5—C6—N2	−179.56 (12)	C9—C8—C10—O1	128.42 (12)
C4—C5—C6—C1	−0.07 (19)	C7—C8—C10—O1	−120.66 (12)
C2—C1—C6—N2	178.93 (12)	C10—O1—C11—C8	2.22 (10)
C2—C1—C6—C5	−0.55 (19)	C10—C8—C11—O1	−2.12 (10)
C6—N2—C7—C8	−155.71 (13)	C9—C8—C11—O1	−128.56 (12)
C9—N2—C7—C8	−3.21 (10)	C7—C8—C11—O1	121.54 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1i	0.95	2.47	3.371 (2)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O1i	0.95	2.47	3.371 (2)	159

Symmetry code: (i) .