6,11-Dihydro-dibenz[b,e]oxepin-11-one.

In the title compound, C(14)H(10)O(2), the seven-membered oxepine ring adopts a twist-boat conformation with a dihedral angle between the mean planes of the two fused benzene rings of 42.0 (1)°. In the crystal, mol-ecules are linked into chains propagating along the c axis by inter-molecular C-H⋯O hydrogen bonds and the chains are arranged in layers parallel to (100).

Related literature

The dibenz[b,e]oxepin nucleus constitutes the fundamental structure of many products with biological activity, see: Kumazawa et al. (1994 ▶). For dibenzo[c,e]thiepine derivatives and their chiroptical properties, see: Truce et al. (1956 ▶); Tomascovic et al. (2000 ▶). For comparative NMR and IR spectral, X-ray structural and theoretical studies of eight related 6-aryl­idenedibenzo[b,e]thiepin-11-one-5,5-dioxides, see: Kolehmainen et al. (2007 ▶). For related structures, see: Bandoli & Nicolini (1982 ▶); Blaton et al. (1995 ▶); Ieawsuwan et al. (2006 ▶); Linden et al. (2004 ▶); Roszak et al. (1996 ▶); Yoshinari & Konno (2009 ▶); Zhang et al. (2008 ▶,2008a ▶). For DFT calculations, see: Hehre et al. (1986 ▶); Schmidt & Polik (2007 ▶). For the GAUSSIAN03 program package, see: Frisch et al. (2004 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C14H10O2

M = 210.22

Monoclinic,

a = 16.5065 (18) Å

b = 4.0806 (7) Å

c = 15.0392 (17) Å

β = 93.654 (10)°

V = 1010.9 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 110 K

0.53 × 0.27 × 0.23 mm

Data collection

Oxford Diffraction Gemini R CCD diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.864, T max = 1.000

1472 measured reflections

968 independent reflections

953 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.108

S = 1.06

968 reflections

145 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809053409/ci2982sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809053409/ci2982Isup2.hkl

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

C14H10O2	F(000) = 440
Mr = 210.22	Dx = 1.381 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 1157 reflections
a = 16.5065 (18) Å	θ = 6.0–73.7°
b = 4.0806 (7) Å	µ = 0.09 mm−1
c = 15.0392 (17) Å	T = 110 K
β = 93.654 (10)°	Thick needle, colorless
V = 1010.9 (2) Å3	0.53 × 0.27 × 0.23 mm
Z = 4

Oxford Diffraction Gemini R CCD diffractometer	968 independent reflections
Radiation source: fine-focus sealed tube	953 reflections with I > 2σ(I)
graphite	Rint = 0.019
Detector resolution: 10.5081 pixels mm-1	θmax = 26.3°, θmin = 3.8°
φ and ω scans	h = −15→20
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −4→2
Tmin = 0.864, Tmax = 1.000	l = −18→17
1472 measured 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0835P)2 + 0.4174P] where P = (Fo2 + 2Fc2)/3
968 reflections	(Δ/σ)max = 0.001
145 parameters	Δρmax = 0.24 e Å−3
2 restraints	Δρmin = −0.24 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
O1	0.45613 (12)	0.6693 (6)	0.53696 (13)	0.0390 (6)
O2	0.63969 (10)	0.7966 (4)	0.34730 (11)	0.0255 (4)
C1	0.49884 (15)	0.7517 (7)	0.47743 (17)	0.0252 (5)
C2	0.58727 (16)	0.8141 (6)	0.49769 (17)	0.0239 (5)
C3	0.61004 (16)	0.8726 (7)	0.58847 (17)	0.0293 (6)
H3A	0.5707	0.8400	0.6311	0.035*
C4	0.68631 (18)	0.9743 (8)	0.61780 (19)	0.0343 (7)
H4A	0.6997	1.0074	0.6795	0.041*
C5	0.74432 (17)	1.0287 (7)	0.5551 (2)	0.0333 (6)
H5A	0.7970	1.1056	0.5740	0.040*
C6	0.72459 (16)	0.9703 (7)	0.46615 (19)	0.0285 (6)
H6A	0.7640	1.0079	0.4240	0.034*
C7	0.64779 (15)	0.8571 (6)	0.43686 (17)	0.0236 (5)
C8	0.57772 (16)	0.5685 (7)	0.31616 (18)	0.0275 (6)
H8A	0.5774	0.3803	0.3577	0.033*
H8B	0.5906	0.4841	0.2570	0.033*
C9	0.49518 (16)	0.7233 (6)	0.30917 (17)	0.0236 (5)
C10	0.45306 (17)	0.7704 (7)	0.22715 (18)	0.0280 (6)
H10A	0.4768	0.7045	0.1741	0.034*
C11	0.37673 (18)	0.9126 (8)	0.22225 (18)	0.0312 (6)
H11A	0.3483	0.9431	0.1659	0.037*
C12	0.34162 (17)	1.0107 (8)	0.29936 (19)	0.0311 (6)
H12A	0.2898	1.1129	0.2958	0.037*
C13	0.38244 (15)	0.9588 (7)	0.38147 (18)	0.0275 (6)
H13A	0.3579	1.0205	0.4344	0.033*
C14	0.45922 (15)	0.8167 (6)	0.38669 (17)	0.0227 (5)

	U11	U22	U33	U12	U13	U23
O1	0.0282 (10)	0.0601 (15)	0.0289 (10)	−0.0057 (10)	0.0042 (8)	0.0139 (10)
O2	0.0203 (9)	0.0282 (9)	0.0285 (10)	0.0004 (8)	0.0056 (7)	−0.0020 (8)
C1	0.0239 (12)	0.0259 (12)	0.0261 (12)	−0.0002 (10)	0.0039 (10)	0.0027 (10)
C2	0.0239 (12)	0.0197 (12)	0.0280 (13)	0.0021 (9)	0.0012 (9)	0.0032 (9)
C3	0.0316 (14)	0.0302 (14)	0.0261 (12)	0.0035 (11)	0.0027 (10)	0.0044 (11)
C4	0.0386 (15)	0.0351 (16)	0.0282 (14)	0.0019 (12)	−0.0067 (12)	−0.0022 (12)
C5	0.0247 (12)	0.0277 (14)	0.0463 (17)	0.0002 (11)	−0.0073 (11)	−0.0028 (12)
C6	0.0226 (11)	0.0231 (13)	0.0401 (14)	0.0010 (9)	0.0035 (10)	−0.0004 (11)
C7	0.0215 (11)	0.0182 (12)	0.0309 (13)	0.0038 (9)	0.0005 (9)	0.0028 (10)
C8	0.0278 (13)	0.0252 (14)	0.0295 (12)	0.0026 (10)	0.0010 (10)	−0.0054 (10)
C9	0.0240 (11)	0.0181 (12)	0.0288 (13)	−0.0041 (9)	0.0018 (9)	−0.0004 (9)
C10	0.0314 (13)	0.0245 (13)	0.0277 (12)	−0.0052 (10)	−0.0015 (10)	−0.0019 (10)
C11	0.0331 (13)	0.0310 (15)	0.0285 (13)	−0.0042 (11)	−0.0066 (10)	0.0034 (11)
C12	0.0218 (11)	0.0300 (14)	0.0410 (15)	0.0013 (9)	−0.0034 (10)	0.0061 (11)
C13	0.0237 (12)	0.0290 (14)	0.0300 (12)	−0.0013 (10)	0.0042 (9)	0.0015 (10)
C14	0.0215 (10)	0.0178 (13)	0.0286 (13)	−0.0028 (9)	−0.0003 (9)	0.0037 (9)

O1—C1	1.221 (3)	C6—H6A	0.95
O2—C7	1.367 (3)	C8—C9	1.499 (3)
O2—C8	1.439 (3)	C8—H8A	0.99
C1—C2	1.494 (3)	C8—H8B	0.99
C1—C14	1.499 (3)	C9—C10	1.390 (4)
C2—C7	1.408 (3)	C9—C14	1.395 (4)
C2—C3	1.413 (4)	C10—C11	1.385 (4)
C3—C4	1.372 (4)	C10—H10A	0.95
C3—H3A	0.95	C11—C12	1.388 (4)
C4—C5	1.403 (4)	C11—H11A	0.95
C4—H4A	0.95	C12—C13	1.385 (4)
C5—C6	1.378 (4)	C12—H12A	0.95
C5—H5A	0.95	C13—C14	1.391 (4)
C6—C7	1.394 (3)	C13—H13A	0.95
C7—O2—C8	117.40 (19)	O2—C8—H8A	109.2
O1—C1—C2	120.0 (2)	C9—C8—H8A	109.2
O1—C1—C14	118.5 (2)	O2—C8—H8B	109.2
C2—C1—C14	121.3 (2)	C9—C8—H8B	109.2
C7—C2—C3	116.8 (2)	H8A—C8—H8B	107.9
C7—C2—C1	127.8 (2)	C10—C9—C14	119.2 (3)
C3—C2—C1	115.0 (2)	C10—C9—C8	121.4 (2)
C4—C3—C2	123.0 (3)	C14—C9—C8	119.3 (2)
C4—C3—H3A	118.5	C11—C10—C9	120.5 (3)
C2—C3—H3A	118.5	C11—C10—H10A	119.8
C3—C4—C5	118.9 (3)	C9—C10—H10A	119.8
C3—C4—H4A	120.5	C10—C11—C12	120.2 (2)
C5—C4—H4A	120.5	C10—C11—H11A	119.9
C6—C5—C4	119.7 (3)	C12—C11—H11A	119.9
C6—C5—H5A	120.1	C13—C12—C11	119.7 (3)
C4—C5—H5A	120.1	C13—C12—H12A	120.1
C5—C6—C7	121.2 (3)	C11—C12—H12A	120.1
C5—C6—H6A	119.4	C12—C13—C14	120.2 (2)
C7—C6—H6A	119.4	C12—C13—H13A	119.9
O2—C7—C6	113.6 (2)	C14—C13—H13A	119.9
O2—C7—C2	126.1 (2)	C9—C14—C13	120.1 (2)
C6—C7—C2	120.3 (2)	C9—C14—C1	121.9 (2)
O2—C8—C9	112.0 (2)	C13—C14—C1	117.9 (2)
O1—C1—C2—C7	168.6 (3)	O2—C8—C9—C10	113.0 (3)
C14—C1—C2—C7	−16.9 (4)	O2—C8—C9—C14	−68.2 (3)
O1—C1—C2—C3	−19.1 (4)	C14—C9—C10—C11	0.9 (4)
C14—C1—C2—C3	155.4 (2)	C8—C9—C10—C11	179.7 (3)
C7—C2—C3—C4	1.6 (4)	C9—C10—C11—C12	0.2 (4)
C1—C2—C3—C4	−171.6 (3)	C10—C11—C12—C13	−1.5 (4)
C2—C3—C4—C5	1.1 (5)	C11—C12—C13—C14	1.6 (4)
C3—C4—C5—C6	−1.9 (4)	C10—C9—C14—C13	−0.8 (4)
C4—C5—C6—C7	−0.1 (4)	C8—C9—C14—C13	−179.6 (2)
C8—O2—C7—C6	156.5 (2)	C10—C9—C14—C1	175.7 (2)
C8—O2—C7—C2	−23.3 (3)	C8—C9—C14—C1	−3.1 (4)
C5—C6—C7—O2	−176.9 (2)	C12—C13—C14—C9	−0.5 (4)
C5—C6—C7—C2	2.9 (4)	C12—C13—C14—C1	−177.1 (2)
C3—C2—C7—O2	176.3 (2)	O1—C1—C14—C9	−141.2 (3)
C1—C2—C7—O2	−11.6 (4)	C2—C1—C14—C9	44.2 (4)
C3—C2—C7—C6	−3.5 (4)	O1—C1—C14—C13	35.3 (4)
C1—C2—C7—C6	168.6 (3)	C2—C1—C14—C13	−139.2 (3)
C7—O2—C8—C9	79.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···O1i	0.95	2.57	3.380 (3)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯O1i	0.95	2.57	3.380 (3)	143

Symmetry code: (i) .