Dibenzo[b,f][1,4]thia­zepin-11-yl-diethyl-amine

Altamura, M.; Guidi, A.; Jierry, L.; Paoli, P.; Rossi, P.

doi:10.1107/S1600536812042328

organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Pages o3133-o3134

doi:10.1107/S1600536812042328

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Dibenzo[b,f][1,4]thiazepin-11-yl-diethyl-amine

Maria Altamura,^a Antonio Guidi,^a Loic Jierry,^b Paola Paoli ^c ^* and Patrizia Rossi ^c

^aChemistry Department, Menarini Ricerche S.p.A., Via dei Sette Santi 3, I-50131 Firenze, Italy, ^bICS, Université de Strasbourg, Strasbourg, France, and ^cDipartimento Energetica "Sergio Stecco", University of Firenze, Via S. Marta 3, I-50139 Firenze, Italy
^*Correspondence e-mail: paolapaoli@unifi.it

(Received 4 October 2012; accepted 9 October 2012; online 13 October 2012)

In the title compound, C₁₇H₁₈N₂S, the thiazepine 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, molecules are connected via weak C_aromatic—H⋯N contacts involving the imine N atom as acceptor and through a quite short C—H⋯π interaction. The resulting molecular 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_r = 282.40
Monoclinic, P 2₁ /c
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 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) 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[F² > 2σ(F²)] = 0.032
wR(F²) = 0.086
S = 1.05
2364 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.26 e Å⁻³

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⋯Cgⁱ	0.95	2.81	3.5759 (18)	139
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); 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 ).

Supporting information

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536812042328/nc2296sup1.cif

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

checkCIF report

Comment top

Many antidepressant drugs have a tricyclic structure with two aromatic rings fused to a central seven membered ring, on which one or more heteroatoms can be present. In this context, dibenzothiazepines are a class of heterocyclic scaffolds containing nitrogen and sulfur which belong to the class of the so-called "privileged structures", i.e. structures "able to provide high affinity ligands for more than one type of receptor" (Evans et al. 1988; Patchett & Nargund 2000; Fedi et al. 2008). In fact the dibenzothiazepine skeleton has a broad spectrum of medical applications; its derivatives are used to treat schizophrenia and also find applications as neuroleptics, antidepressants, antihistaminic, just to name a few (Ganesh et al. 2011; Pettersson et al. 2009; Riedel et al. 2007; Warawa et al. 2001). Within our programme research concerning the structural elucidation of tricyclic molecules in order to gain further insights into structure–property relationships (Altamura et al., 2008; Altamura et al., 2009; Altamura et al., 2011) we investigated the crystal and molecular structure of the title compound. The overall shape of the tricyclic skeleton is controlled both by the conformation of the central seven-membered ring and the relative arrangement of the aromatic rings bound to it. The central thiazepine ring adopts the usual boat conformation, with C1, C2, C8 and C9 as the basal plane, the S atom as the bow and the N1—C7 bond as the stern. The deviation from a pure boat conformation is quite small as can be seen from the asymmetry index ΔC_s which is 3.97°; the bow angle is 51.04 (8)° and the stern angle is 41.89 (8)°(Duax et al. 1976; Bertolasi et al. 1982; Ravikumar & Sridhar, 2005). Finally, the dihedral angle between the benzene rings is 104.08 (5)°. As a consequence the dibenzothiazepine tricyclic skeleton assumes an overall butterfly-like shape (Fig. 1). The N2—C7 bond is shorter than an usual N—C single bond [1.368 (2) Å compared to 1.416 Å (Allen et al. 1987)] and the sum of the bond angles about N2 is 358°; consequently, N2 has a partial sp² character. Molecular chains, which propagate along the c axis, are formed through intermolecular interactions (Fig. 2): a weak C—H_aromatic···N contact which involves the imine nitrogen atom as acceptor and a quite short C—H···π interaction (Table 1).

Related literature top

For `privileged structures', 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 top

The synthesis of the title compound started from the commercially available tricyclic lactam (dibenzo[b,f][1,4]thiazepin-11(10H)-one) (0.89 g, 3.91 mmol), that was dissolved into 10 ml of phosphorus oxychloride and refluxed for two hours under nitrogen atmosphere. After removal of excess POCl₃ under vacuum, the corresponding iminochloride (11-chlorodibenzo[b,f][1,4]thiazepine) was obtained as a yellow oil, that was dissolved in 20 ml of anhydrous toluene. An excess of diethylamine (20 ml, 191 mmol) was added and the mixture refluxed until complete conversion (monitored by HPLC; about 6 h were needed for complete conversion). After removal of the solvent in vacuo and purification by flash chromatography (eluent: gradient CH₂Cl₂/cyclohexane from 50:50 to 100% CH₂Cl₂), dibenzo[b,f][1,4]thiazepin-11-yl-diethyl-amine was obtained as a yellow oil (0.66 g, 60% yield), which became a white solid on standing at room temperature for several days. Crystals suitable for single-crystal X-ray diffraction analysis were obtained by slow evaporation of a water/DMSO solution of dibenzo[b,f][1,4]thiazepin-11-yl-diethyl-amine.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis CCD (Oxford Diffraction, 2006); 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).

Figures top

	Fig. 1. Crystal structure of the title compound with labelling and displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Crystal structure of the title compound with view along the b-axis. Intermolecular H-bonding interactions are shown as dashed lines.

Dibenzo[b,f][1,4]thiazepin-11-yl-diethyl-amine top

Crystal data top

C₁₇H₁₈N₂S	F(000) = 600
M_r = 282.40	D_x = 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

Data collection top

Oxford Diffraction XcaliburPX diffractometer	2364 independent reflections
Radiation source: Enhance (Cu) X-ray Source	1837 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
Detector resolution: 8.1241 pixels mm^-1	θ_max = 64.7°, θ_min = 3.8°
ω scans	h = −13→11
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = −9→9
T_min = 0.722, T_max = 0.945	l = −16→17
6173 measured reflections

Refinement top

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(F_o²) + (0.0564P)²] where P = (F_o² + 2F_c²)/3
2364 reflections	(Δ/σ)_max < 0.001
181 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₇H₁₈N₂S	V = 1449.54 (4) Å³
M_r = 282.40	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 12.0137 (2) Å	µ = 1.89 mm⁻¹
b = 8.2257 (1) Å	T = 150 K
c = 15.0513 (2) Å	0.20 × 0.18 × 0.03 mm
β = 102.952 (1)°

Data collection top

Oxford Diffraction XcaliburPX diffractometer	2364 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	1837 reflections with I > 2σ(I)
T_min = 0.722, T_max = 0.945	R_int = 0.019
6173 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.086	H-atom parameters constrained
S = 1.05	Δρ_max = 0.23 e Å⁻³
2364 reflections	Δρ_min = −0.26 e Å⁻³
181 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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···Cgⁱ	0.95	2.81	3.5759 (18)	139

Symmetry code: (i) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₈N₂S
M_r	282.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	12.0137 (2), 8.2257 (1), 15.0513 (2)
β (°)	102.952 (1)
V (Å³)	1449.54 (4)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	1.89
Crystal size (mm)	0.20 × 0.18 × 0.03

Data collection
Diffractometer	Oxford Diffraction XcaliburPX diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2006)
T_min, T_max	0.722, 0.945
No. of measured, independent and observed [I > 2σ(I)] reflections	6173, 2364, 1837
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.586

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.086, 1.05
No. of reflections	2364
No. of parameters	181
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.26

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SIR92 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PARST (Nardelli, 1995).

Hydrogen-bond geometry (Å, º) top

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···Cgⁱ	0.95	2.81	3.5759 (18)	139

Symmetry code: (i) x, −y+1/2, z+1/2.

Acknowledgements

The authors acknowledge the CRIST (Centro di Cristallografia Strutturale, University of Firenze) where the data collection was performed.

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Volume 68| Part 11| November 2012| Pages o3133-o3134

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