Dibenzo[b,f][1,4]thia-zepin-11-yl-diethyl-amine.

In the title compound, C(17)H(18)N(2)S, the thia-zepine ring adopts a boat conformation and the dihedral angle between the benzene rings is 75.92 (5)°, resulting in a butterfly-like conformation. In the crystal, mol-ecules are connected via weak C(aromatic)-H⋯N contacts involving the imine N atom as acceptor and through a quite short C-H⋯π inter-action. The resulting mol-ecular chains propagate along the c-axis direction.

Related literature

For ‘privileged structures’, that is ‘structures able to provide high affinity ligands for more than one type of receptor’, see: Evans et al. (1988 ▶); Patchett & Nargund (2000 ▶); Fedi et al. (2008 ▶). For the clinical use of dibenzothia­zepine derivatives, see: Ganesh et al. (2011 ▶); Pettersson et al. (2009 ▶); Riedel et al. (2007 ▶); Warawa et al. (2001 ▶). For structure–property relationships in (6,7,6)-tricyclic ring systems, see: Ravikumar & Sridhar (2005 ▶); Altamura et al. (2008 ▶, 2009 ▶, 2011 ▶). For geometrical data and descriptors, see: Duax et al. (1976 ▶); Bertolasi et al. (1982 ▶); Allen et al. (1987 ▶).

Experimental

Crystal data

C17H18N2S

M = 282.40

Monoclinic,

a = 12.0137 (2) Å

b = 8.2257 (1) Å

c = 15.0513 (2) Å

β = 102.952 (1)°

V = 1449.54 (4) Å3

Z = 4

Cu Kα radiation

μ = 1.89 mm−1

T = 150 K

0.20 × 0.18 × 0.03 mm

Data collection

Oxford Diffraction XcaliburPX diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 ▶) T min = 0.722, T max = 0.945

6173 measured reflections

2364 independent reflections

1837 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.086

S = 1.05

2364 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PARST (Nardelli, 1995 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536812042328/nc2296sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812042328/nc2296Isup2.hkl

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

C17H18N2S	F(000) = 600
Mr = 282.40	Dx = 1.294 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.5418 Å
a = 12.0137 (2) Å	Cell parameters from 3716 reflections
b = 8.2257 (1) Å	θ = 3.8–64.6°
c = 15.0513 (2) Å	µ = 1.89 mm−1
β = 102.952 (1)°	T = 150 K
V = 1449.54 (4) Å3	Platelet, colourless
Z = 4	0.20 × 0.18 × 0.03 mm

Oxford Diffraction XcaliburPX diffractometer	2364 independent reflections
Radiation source: Enhance (Cu) X-ray Source	1837 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
Detector resolution: 8.1241 pixels mm-1	θmax = 64.7°, θmin = 3.8°
ω scans	h = −13→11
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = −9→9
Tmin = 0.722, Tmax = 0.945	l = −16→17
6173 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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0564P)2] where P = (Fo2 + 2Fc2)/3
2364 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.83045 (3)	0.13292 (5)	0.85602 (3)	0.01958 (15)
N1	0.67962 (11)	0.44375 (17)	0.84814 (9)	0.0179 (3)
N2	0.51660 (11)	0.33602 (17)	0.87760 (9)	0.0181 (3)
C1	0.69759 (13)	0.2400 (2)	0.97172 (11)	0.0177 (4)
C2	0.78691 (14)	0.1378 (2)	0.96160 (11)	0.0175 (4)
C3	0.84541 (14)	0.0447 (2)	1.03477 (11)	0.0198 (4)
H3	0.9047	−0.0264	1.0268	0.024*
C4	0.81731 (14)	0.0556 (2)	1.11916 (11)	0.0211 (4)
H4	0.8564	−0.0089	1.1687	0.025*
C5	0.73182 (14)	0.1613 (2)	1.13056 (11)	0.0211 (4)
H5	0.7137	0.1715	1.1886	0.025*
C6	0.67280 (13)	0.2522 (2)	1.05782 (11)	0.0197 (4)
H6	0.6143	0.3241	1.0666	0.024*
C7	0.63322 (13)	0.3418 (2)	0.89419 (11)	0.0169 (4)
C8	0.79782 (14)	0.4649 (2)	0.85930 (11)	0.0188 (4)
C9	0.87701 (14)	0.3391 (2)	0.85923 (11)	0.0188 (4)
C10	0.99058 (14)	0.3727 (2)	0.85997 (11)	0.0237 (4)
H10	1.0430	0.2861	0.8604	0.028*
C11	1.02769 (15)	0.5322 (2)	0.86002 (12)	0.0290 (5)
H11	1.1051	0.5551	0.8596	0.035*
C12	0.95124 (15)	0.6578 (2)	0.86075 (12)	0.0280 (5)
H12	0.9767	0.7673	0.8618	0.034*
C13	0.83815 (14)	0.6251 (2)	0.86002 (11)	0.0218 (4)
H13	0.7867	0.7128	0.8600	0.026*
C14	0.45010 (14)	0.2064 (2)	0.90866 (11)	0.0200 (4)
H14A	0.5032	0.1237	0.9421	0.024*
H14B	0.4014	0.1529	0.8548	0.024*
C15	0.37461 (15)	0.2692 (2)	0.97035 (12)	0.0252 (4)
H15A	0.3324	0.1782	0.9891	0.038*
H15B	0.3206	0.3493	0.9371	0.038*
H15C	0.4224	0.3203	1.0245	0.038*
C16	0.45022 (14)	0.4423 (2)	0.80635 (11)	0.0188 (4)
H16A	0.4865	0.5510	0.8112	0.023*
H16B	0.3723	0.4555	0.8170	0.023*
C17	0.44140 (14)	0.3772 (2)	0.71044 (11)	0.0209 (4)
H17A	0.3965	0.4527	0.6661	0.031*
H17B	0.4039	0.2707	0.7046	0.031*
H17C	0.5181	0.3662	0.6988	0.031*

	U11	U22	U33	U12	U13	U23
S1	0.0205 (2)	0.0207 (3)	0.0190 (2)	−0.00074 (18)	0.00747 (17)	−0.00055 (18)
N1	0.0153 (7)	0.0199 (8)	0.0191 (7)	−0.0019 (6)	0.0049 (6)	−0.0011 (6)
N2	0.0153 (7)	0.0197 (8)	0.0196 (8)	−0.0014 (6)	0.0042 (6)	0.0016 (6)
C1	0.0148 (8)	0.0195 (9)	0.0187 (9)	−0.0059 (7)	0.0034 (7)	−0.0009 (7)
C2	0.0163 (9)	0.0188 (9)	0.0177 (9)	−0.0058 (7)	0.0041 (7)	−0.0019 (7)
C3	0.0170 (9)	0.0189 (10)	0.0232 (9)	−0.0023 (7)	0.0041 (7)	−0.0009 (8)
C4	0.0190 (10)	0.0234 (10)	0.0190 (9)	−0.0051 (8)	0.0003 (7)	0.0029 (8)
C5	0.0192 (9)	0.0286 (10)	0.0156 (9)	−0.0079 (8)	0.0043 (7)	−0.0029 (7)
C6	0.0154 (9)	0.0233 (10)	0.0202 (9)	−0.0046 (8)	0.0035 (7)	−0.0041 (7)
C7	0.0172 (9)	0.0175 (9)	0.0162 (8)	0.0000 (7)	0.0043 (7)	−0.0041 (7)
C8	0.0177 (9)	0.0232 (10)	0.0150 (8)	−0.0038 (7)	0.0023 (7)	−0.0002 (7)
C9	0.0190 (9)	0.0230 (10)	0.0144 (8)	−0.0041 (7)	0.0037 (7)	0.0013 (7)
C10	0.0171 (9)	0.0309 (11)	0.0230 (9)	0.0009 (8)	0.0044 (7)	0.0037 (8)
C11	0.0164 (9)	0.0389 (12)	0.0312 (11)	−0.0071 (9)	0.0044 (8)	0.0044 (9)
C12	0.0235 (10)	0.0276 (11)	0.0316 (11)	−0.0108 (8)	0.0035 (8)	0.0012 (9)
C13	0.0201 (9)	0.0207 (10)	0.0247 (10)	−0.0018 (8)	0.0055 (8)	−0.0008 (8)
C14	0.0177 (9)	0.0208 (10)	0.0211 (9)	−0.0025 (8)	0.0039 (7)	−0.0011 (8)
C15	0.0229 (10)	0.0295 (11)	0.0250 (9)	−0.0061 (8)	0.0090 (8)	0.0001 (8)
C16	0.0159 (9)	0.0172 (9)	0.0233 (9)	0.0016 (7)	0.0046 (7)	0.0018 (7)
C17	0.0182 (9)	0.0224 (10)	0.0214 (9)	0.0024 (8)	0.0031 (7)	0.0020 (7)

S1—C2	1.7814 (16)	C9—C10	1.390 (2)
S1—C9	1.7831 (18)	C10—C11	1.385 (3)
N1—C7	1.291 (2)	C10—H10	0.9500
N1—C8	1.403 (2)	C11—C12	1.384 (3)
N2—C7	1.368 (2)	C11—H11	0.9500
N2—C14	1.470 (2)	C12—C13	1.383 (2)
N2—C16	1.472 (2)	C12—H12	0.9500
C1—C6	1.397 (2)	C13—H13	0.9500
C1—C2	1.398 (2)	C14—C15	1.526 (2)
C1—C7	1.502 (2)	C14—H14A	0.9900
C2—C3	1.395 (2)	C14—H14B	0.9900
C3—C4	1.388 (2)	C15—H15A	0.9800
C3—H3	0.9500	C15—H15B	0.9800
C4—C5	1.385 (2)	C15—H15C	0.9800
C4—H4	0.9500	C16—C17	1.521 (2)
C5—C6	1.383 (2)	C16—H16A	0.9900
C5—H5	0.9500	C16—H16B	0.9900
C6—H6	0.9500	C17—H17A	0.9800
C8—C13	1.403 (2)	C17—H17B	0.9800
C8—C9	1.406 (2)	C17—H17C	0.9800
C2—S1—C9	96.16 (8)	C9—C10—H10	119.9
C7—N1—C8	124.28 (14)	C12—C11—C10	119.53 (17)
C7—N2—C14	125.08 (14)	C12—C11—H11	120.2
C7—N2—C16	118.54 (14)	C10—C11—H11	120.2
C14—N2—C16	114.71 (13)	C13—C12—C11	120.46 (17)
C6—C1—C2	118.19 (15)	C13—C12—H12	119.8
C6—C1—C7	120.08 (15)	C11—C12—H12	119.8
C2—C1—C7	121.64 (14)	C12—C13—C8	121.32 (17)
C3—C2—C1	120.48 (15)	C12—C13—H13	119.3
C3—C2—S1	119.67 (13)	C8—C13—H13	119.3
C1—C2—S1	119.79 (13)	N2—C14—C15	112.82 (14)
C4—C3—C2	120.26 (16)	N2—C14—H14A	109.0
C4—C3—H3	119.9	C15—C14—H14A	109.0
C2—C3—H3	119.9	N2—C14—H14B	109.0
C5—C4—C3	119.52 (16)	C15—C14—H14B	109.0
C5—C4—H4	120.2	H14A—C14—H14B	107.8
C3—C4—H4	120.2	C14—C15—H15A	109.5
C6—C5—C4	120.27 (15)	C14—C15—H15B	109.5
C6—C5—H5	119.9	H15A—C15—H15B	109.5
C4—C5—H5	119.9	C14—C15—H15C	109.5
C5—C6—C1	121.19 (16)	H15A—C15—H15C	109.5
C5—C6—H6	119.4	H15B—C15—H15C	109.5
C1—C6—H6	119.4	N2—C16—C17	113.16 (14)
N1—C7—N2	118.19 (15)	N2—C16—H16A	108.9
N1—C7—C1	124.74 (14)	C17—C16—H16A	108.9
N2—C7—C1	116.77 (14)	N2—C16—H16B	108.9
N1—C8—C13	117.10 (16)	C17—C16—H16B	108.9
N1—C8—C9	125.17 (16)	H16A—C16—H16B	107.8
C13—C8—C9	117.30 (15)	C16—C17—H17A	109.5
C10—C9—C8	121.12 (16)	C16—C17—H17B	109.5
C10—C9—S1	119.41 (14)	H17A—C17—H17B	109.5
C8—C9—S1	119.46 (13)	C16—C17—H17C	109.5
C11—C10—C9	120.26 (17)	H17A—C17—H17C	109.5
C11—C10—H10	119.9	H17B—C17—H17C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···N1i	0.95	2.70	3.576 (2)	154
C4—H4···Cgi	0.95	2.81	3.5759 (18)	139

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C8–C12 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯N1i	0.95	2.70	3.576 (2)	154
C4—H4⋯Cg i	0.95	2.81	3.5759 (18)	139

Symmetry code: (i) .