5,7-Dihydro-dibenzo[c,e]thiepine.

In the title compound, C(14)H(12)S, the central seven-membered C(6)S ring has a twist-boat conformation. The dihedral angle between the two benzene rings is 52.4 (1)°.

Related literature

For the preparation of a pair of atrop diastereomeric RhIII complexes having a 2,2′-bis­(2-amino­ethyl­thio­meth­yl)-1,1′-biphenyl ligand, see: Yoshinari & Konno (2008 ▶). For the synthesis, see: Foubelo et al. (2005 ▶).

Experimental

Crystal data

C14H12S

M = 212.30

Monoclinic,

a = 5.645 (3) Å

b = 17.316 (9) Å

c = 11.398 (5) Å

β = 92.444 (19)°

V = 1113.1 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 200 K

0.15 × 0.15 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (; Higashi, 1995 ▶) T min = 0.962, T max = 0.975

7548 measured reflections

2464 independent reflections

1324 reflections with I > 2σ(I)

R int = 0.114

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.165

S = 1.06

2464 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.30 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809008769/is2397sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809008769/is2397Isup2.hkl

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

C14H12S	F(000) = 448
Mr = 212.30	Dx = 1.267 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2yn	Cell parameters from 4537 reflections
a = 5.645 (3) Å	θ = 3.6–27.5°
b = 17.316 (9) Å	µ = 0.25 mm−1
c = 11.398 (5) Å	T = 200 K
β = 92.444 (19)°	Prismatic, colourless
V = 1113.1 (10) Å3	0.15 × 0.15 × 0.10 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	2464 independent reflections
Radiation source: fine-focus sealed tube	1324 reflections with I > 2σ(I)
graphite	Rint = 0.114
Detector resolution: 10.00 pixels mm-1	θmax = 27.5°, θmin = 3.6°
ω scans	h = −4→7
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −22→22
Tmin = 0.962, Tmax = 0.975	l = −14→14
7548 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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.165	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0655P)2] where P = (Fo2 + 2Fc2)/3
2464 reflections	(Δ/σ)max < 0.001
136 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.30 e Å−3
0 constraints

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
S1	1.27862 (17)	0.41043 (5)	−0.05701 (6)	0.0391 (3)
C1	1.3831 (7)	0.39078 (19)	0.0932 (2)	0.0357 (8)
H1	1.4103	0.3346	0.1023	0.043*
H2	1.5369	0.4172	0.1083	0.043*
C2	1.2131 (6)	0.41676 (17)	0.1826 (2)	0.0281 (7)
C3	1.2565 (7)	0.48526 (17)	0.2447 (2)	0.0330 (8)
H3	1.3926	0.5153	0.2294	0.040*
C4	1.1020 (7)	0.50965 (19)	0.3284 (2)	0.0363 (9)
H4	1.1289	0.5572	0.3684	0.044*
C5	0.9098 (6)	0.4648 (2)	0.3532 (2)	0.0363 (9)
H5	0.8061	0.4810	0.4120	0.044*
C6	0.8660 (6)	0.39652 (19)	0.2937 (2)	0.0332 (8)
H6	0.7331	0.3659	0.3123	0.040*
C7	1.0160 (6)	0.37196 (17)	0.2059 (2)	0.0276 (8)
C8	0.9612 (6)	0.30059 (17)	0.1387 (2)	0.0293 (7)
C9	0.9182 (7)	0.23099 (19)	0.1957 (3)	0.0369 (8)
H7	0.9236	0.2295	0.2790	0.044*
C10	0.8682 (7)	0.1646 (2)	0.1335 (3)	0.0420 (9)
H8	0.8406	0.1176	0.1738	0.050*
C11	0.8582 (8)	0.1662 (2)	0.0120 (3)	0.0483 (10)
H9	0.8242	0.1204	−0.0313	0.058*
C12	0.8979 (7)	0.23477 (19)	−0.0461 (3)	0.0395 (9)
H10	0.8892	0.2357	−0.1295	0.047*
C13	0.9499 (6)	0.30201 (17)	0.0150 (2)	0.0270 (7)
C14	0.9761 (6)	0.37741 (18)	−0.0492 (2)	0.0320 (8)
H11	0.8833	0.4175	−0.0095	0.038*
H12	0.9073	0.3716	−0.1300	0.038*

	U11	U22	U33	U12	U13	U23
S1	0.0500 (6)	0.0390 (5)	0.0295 (4)	−0.0065 (5)	0.0140 (4)	0.0003 (4)
C1	0.038 (2)	0.0342 (19)	0.0360 (16)	−0.0057 (17)	0.0081 (14)	−0.0011 (14)
C2	0.041 (2)	0.0229 (16)	0.0206 (13)	0.0035 (15)	0.0040 (12)	0.0033 (12)
C3	0.046 (2)	0.0246 (17)	0.0286 (15)	−0.0038 (16)	0.0003 (14)	0.0045 (13)
C4	0.057 (3)	0.0234 (17)	0.0289 (16)	0.0046 (17)	0.0016 (15)	−0.0023 (13)
C5	0.044 (2)	0.041 (2)	0.0239 (15)	0.0118 (18)	0.0062 (14)	−0.0004 (14)
C6	0.039 (2)	0.039 (2)	0.0226 (14)	−0.0031 (16)	0.0078 (13)	0.0036 (13)
C7	0.038 (2)	0.0242 (17)	0.0213 (14)	0.0017 (15)	0.0039 (13)	0.0045 (12)
C8	0.033 (2)	0.0237 (17)	0.0312 (15)	−0.0039 (15)	0.0029 (13)	0.0009 (12)
C9	0.045 (2)	0.0331 (19)	0.0326 (16)	−0.0082 (17)	−0.0004 (14)	0.0038 (14)
C10	0.048 (3)	0.0267 (19)	0.051 (2)	−0.0082 (18)	−0.0012 (17)	0.0045 (15)
C11	0.069 (3)	0.027 (2)	0.048 (2)	−0.009 (2)	−0.0008 (18)	−0.0093 (15)
C12	0.056 (3)	0.0317 (19)	0.0310 (16)	−0.0033 (18)	0.0023 (15)	−0.0054 (14)
C13	0.0226 (18)	0.0290 (18)	0.0296 (15)	−0.0006 (15)	0.0033 (12)	0.0012 (12)
C14	0.043 (2)	0.0316 (18)	0.0216 (14)	0.0011 (17)	0.0045 (13)	0.0035 (12)

S1—C14	1.807 (4)	C7—C8	1.480 (4)
S1—C1	1.819 (3)	C8—C9	1.395 (4)
C1—C2	1.499 (4)	C8—C13	1.409 (4)
C1—H1	0.9900	C9—C10	1.374 (5)
C1—H2	0.9900	C9—H7	0.9500
C2—C7	1.391 (4)	C10—C11	1.384 (4)
C2—C3	1.397 (4)	C10—H8	0.9500
C3—C4	1.386 (5)	C11—C12	1.382 (5)
C3—H3	0.9500	C11—H9	0.9500
C4—C5	1.373 (5)	C12—C13	1.382 (4)
C4—H4	0.9500	C12—H10	0.9500
C5—C6	1.381 (4)	C13—C14	1.507 (4)
C5—H5	0.9500	C14—H11	0.9900
C6—C7	1.404 (4)	C14—H12	0.9900
C6—H6	0.9500
C14—S1—C1	99.41 (15)	C9—C8—C13	118.6 (3)
C2—C1—S1	113.1 (3)	C9—C8—C7	121.2 (2)
C2—C1—H1	109.0	C13—C8—C7	120.2 (2)
S1—C1—H1	109.0	C10—C9—C8	121.3 (3)
C2—C1—H2	109.0	C10—C9—H7	119.3
S1—C1—H2	109.0	C8—C9—H7	119.3
H1—C1—H2	107.8	C9—C10—C11	119.8 (3)
C7—C2—C3	120.1 (3)	C9—C10—H8	120.1
C7—C2—C1	120.2 (3)	C11—C10—H8	120.1
C3—C2—C1	119.7 (3)	C12—C11—C10	119.8 (3)
C4—C3—C2	120.3 (3)	C12—C11—H9	120.1
C4—C3—H3	119.8	C10—C11—H9	120.1
C2—C3—H3	119.8	C13—C12—C11	121.2 (3)
C5—C4—C3	119.7 (3)	C13—C12—H10	119.4
C5—C4—H4	120.1	C11—C12—H10	119.4
C3—C4—H4	120.1	C12—C13—C8	119.3 (3)
C4—C5—C6	120.6 (3)	C12—C13—C14	120.6 (3)
C4—C5—H5	119.7	C8—C13—C14	120.0 (3)
C6—C5—H5	119.7	C13—C14—S1	114.2 (2)
C5—C6—C7	120.6 (3)	C13—C14—H11	108.7
C5—C6—H6	119.7	S1—C14—H11	108.7
C7—C6—H6	119.7	C13—C14—H12	108.7
C2—C7—C6	118.6 (3)	S1—C14—H12	108.7
C2—C7—C8	121.2 (3)	H11—C14—H12	107.6
C6—C7—C8	120.2 (3)
C14—S1—C1—C2	−45.4 (3)	C2—C7—C8—C13	−51.6 (5)
S1—C1—C2—C7	79.6 (3)	C6—C7—C8—C13	127.2 (3)
S1—C1—C2—C3	−102.0 (3)	C13—C8—C9—C10	0.7 (5)
C7—C2—C3—C4	−1.0 (5)	C7—C8—C9—C10	−179.7 (4)
C1—C2—C3—C4	−179.4 (3)	C8—C9—C10—C11	−0.5 (5)
C2—C3—C4—C5	2.2 (5)	C9—C10—C11—C12	−0.2 (6)
C3—C4—C5—C6	−1.5 (5)	C10—C11—C12—C13	0.6 (6)
C4—C5—C6—C7	−0.5 (5)	C11—C12—C13—C8	−0.4 (6)
C3—C2—C7—C6	−1.0 (4)	C11—C12—C13—C14	−175.8 (4)
C1—C2—C7—C6	177.4 (3)	C9—C8—C13—C12	−0.3 (5)
C3—C2—C7—C8	177.8 (3)	C7—C8—C13—C12	−179.8 (3)
C1—C2—C7—C8	−3.7 (4)	C9—C8—C13—C14	175.1 (3)
C5—C6—C7—C2	1.8 (4)	C7—C8—C13—C14	−4.4 (5)
C5—C6—C7—C8	−177.1 (3)	C12—C13—C14—S1	−105.8 (3)
C2—C7—C8—C9	128.8 (3)	C8—C13—C14—S1	78.8 (3)
C6—C7—C8—C9	−52.3 (5)	C1—S1—C14—C13	−43.6 (2)