11-[3-(Dimethyl­amino)prop­yl]-6,11-dihydro­dibenzo[b,e]thiepin-11-ol

Jasinski, J.P.; Butcher, R.J.; Hakim Al-arique, Q.N.M.; Yathirajan, H.S.; Ramesha, A.R.

doi:10.1107/S1600536809053434

organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Pages o161-o162

doi:10.1107/S1600536809053434

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11-[3-(Dimethylamino)propyl]-6,11-dihydrodibenzo[b,e]thiepin-11-ol

Jerry P. Jasinski,^a ^* Ray J. Butcher,^b Q. N. M. Hakim Al-arique,^c H. S. Yathirajan ^c and A.R. Ramesha ^d

^aDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, ^bDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, ^cDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, 570 006, India, and ^dRL Fine Chem, Bangalore, 560 064, India
^*Correspondence e-mail: jjasinski@keene.edu

(Received 6 December 2009; accepted 11 December 2009; online 16 December 2009)

There are two independent molecules (A and B) in the asymmetric unit of the title compound, C₁₉H₂₃NOS. In each molecule, the seven-membered thiepine ring is bent into a slightly twisted V-shape. The dihedral angles between the mean planes of the two benzene rings fused to the thiepine ring are 75.7 (5) in molecule A and 73.8 (4)° in molecule B. In both molecules, an intramolecular O—H⋯N hydrogen bond occurs. In the crystal, weak intermolecular C—H⋯O and C—H⋯π-ring interactions are observed.

Related literature

For related structures, see: Bandoli & Nicolini, (1982 ); Blaton et al. (1995 ); Ieawsuwan et al. (2006 ); Linden et al. (2004 ); Portalone et al. (2007 ); Roszak et al. (1996 ); Rudorf et al. (1999 ); Yoshinari & Konno, (2009 ); Zhang et al. (2008 ,2008a ). For related background, see: Rudorf et al. (1999). For antidepressant and anti-inflammatory properties, see: Rajsner et al. (1969 , 1971 ); Rooks et al. (1980 ); Tomascovic et al. (2000 ); Truce et al. (1956 ). For pharmacological synthesis and studies, see: Ikuo et al. (1978 ); Uchida et al. (1979 ); Wyatt et al. (2006 ). For NMR, Ir and X-ray studies, see: Kolehmainen et al. (2007 ). For density functional theory (DFT), see: Becke (1988 , 1993 ); Frisch et al. (2004 ); Hehre et al. (1986 ); Lee et al. (1988 ); Schmidt & Polik (2007 ).

Experimental

Crystal data

C₁₉H₂₃NOS
M_r = 313.44
Monoclinic, P 2₁ /n
a = 7.7215 (4) Å
b = 15.3729 (10) Å
c = 27.9274 (16) Å
β = 95.401 (6)°
V = 3300.3 (3) Å³
Z = 8
Cu Kα radiation
μ = 1.74 mm⁻¹
T = 110 K
0.51 × 0.42 × 0.14 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.432, T_max = 1.000
14666 measured reflections
6565 independent reflections
5490 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.153
S = 1.05
6565 reflections
403 parameters
H-atom parameters constrained
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.56 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1A—H1A⋯N1A	0.84	1.86	2.693 (2)	170
O1B—H1B⋯N1B	0.84	1.84	2.679 (2)	174
C4A—H4AA⋯O1B	0.95	2.51	3.253 (2)	135
C3A—H3AA⋯Cg7ⁱ	0.95	2.74	3.526 (6)	140
C17A—H17A⋯Cg1ⁱⁱ	0.99	2.67	3.537 (7)	147
C17A—H17B⋯Cg2ⁱⁱ	0.99	2.75	3.720 (3)	167
C17B—H17C⋯Cg8ⁱⁱⁱ	0.99	2.68	3.663 (6)	170
C17B—17D⋯Cg7ⁱⁱⁱ	0.99	2.64	3.538 (1)	149
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x+1, y, z; (iii) x-1, y, z. Cg1, Cg2, Cg7 and Cg8 are the centroids of the C1A—C6A, C8A—C13A, C1B–C6B and C8B—C13B rings, respectively.

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); data reduction: CrysAlis RED; 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 (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809053434/lh2968sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809053434/lh2968Isup2.hkl

checkCIF report

Comment top

The title compound, (I), C₁₉H₂₃NOS, is a derivative of 6,11-dihydrodibenzo[b,e]thiepin-11-one, which is used as an intermediate for the synthesis of dosulepin, an antidepressant of the tricyclic family. The dibenzo[c,e]thiepine derivatives (Truce et al., 1956) exhibit remarkable chiroptical properties (Tomascovic et al., 2000). The anti-inflammatory and analgesic profile of 6,11-dihydrodibenzo[b,e]thiepin-11-one-3-acetic acid (Tiopinac) is reported (Rooks II et al., 1980). Dibenzo[b,e]thiepin-5,5-dioxide derivatives are known to possess antihistaminic and antiallergenic activities (Rajsner et al., 1971). In addition, by aminoalkylation of 6,11-dihydrodibenzo[b,e]thiepin-5,5-dioxide and the corresponding 11-ketone, compounds with neurotropic and psychotropic activities have been reported (Rajsner et al., 1969). Also, the comparative NMR and IR spectral, X-ray structural and theoretical studies of eight 6-arylidenedibenzo[b,e]thiepin-11-one-5,5-dioxides have been reported (Kolehmainen et al., 2007). A pharmacological study of [2-chloro-11-(2-dimethylaminoethoxy)dibenzo(b,f)thiepine] (zotepine), and a new neuroleptic drug are also reported (Uchida et al., 1979). In addition, the synthesis and chemistry of enantiomerically pure 10,11-dihydrobenzo[b,f]thiepines (Wyatt et al., 2006) and the synthesis and pharmacological properties of 8-chloro-10-(2-dimethylaminoethoxy) dibenzo[b,f]thiepine and related compounds have been reported (Ikuo et al., 1978). In view of the importance of thiepines, this paper reports the crystal structure of the title compound, C₁₉H₂₃NOS, (I).

The title compound, C₁₉H₂₃NOS, (I), crystallizes with two independent molecules (A, Fig. 1 & B, Fig. 2) in the asymmetric unit. The seven-membered thiepine ring is bent into a slightly twisted V-shaped arrangement with sp3 hybridized atoms at C7(A & B), C14(A & B)and S1(A & B). The dihedral angles between the mean planes of the two benzene rings fused to the thiepine ring are 75.7 (5)° (A) and 73.8 (4)° (B), respectively. An intramolecular O—H···N hydrogen bond exists between the hydroxy group and the N atom from the (dimethylamino)propyl group both bonded to the C14 atom of the thiepine ring (O1A—H1A···N1A & O1B—H1B···N1; Table 1). While no classical intermolecular hydrogen bonds are present, weak C–H···O and C–H···π-ring intermolecular interactions are observed which contribute to the stability of crystal packing (Fig.3, Table 1,2).

Following a geometry optimization density functional theory calculation (Schmidt & Polik 2007) at the B3LYP 6–31-G(d) level (Becke, 1988, 1993; Lee et al. 1988; Hehre et al. 1986) with the Gaussian03 program package (Frisch at al. 2004) the angle between the mean planes of the two benzene rings changes to 73.4 (4)°, a difference of -2.32° (A) and + 0.40° (B), respectively. These results support the collective effects of the intra and intermolecular hydrogen bonding described above slightly influencing crystal packing.

Related literature top

For related structures, see: Bandoli & Nicolini, (1982); Blaton et al. (1995); Ieawsuwan et al. (2006); Linden et al. (2004); Portalone et al. (2007); Roszak et al. (1996); Rudorf et al. (1999); Yoshinari & Konno, (2009); Zhang et al. (2008,2008a). For related background, see: Ikuo et al. (1978); Kolehmainen et al. (2007); Rajsner et al. (1969, 1971); Rooks et al. (1980); Rudorf et al. (1999); Tomascovic et al. (2000); Truce et al. (1956); Uchida et al. (1979); Wyatt et al. (2006). For density functional theory (DFT), see: Becke (1988, 1993); Frisch et al., (2004); Hehre et al. (1986); Lee et al. (1988); Schmidt & Polik (2007).

Experimental top

The title compound was obtained as a gift sample from R. L. Fine Chem, Bangalore, India. The compound was used without further purification. X-ray quality crystals (m.p. 433–435 K) of the title compound, (I), were obtained by slow evaporation from acetone solution.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of molecule A in (I) showing the atom labeling scheme and 50% probability displacement ellipsoids.
	Fig. 2. Molecular structure of molecule B in (I) showing the atom labeling scheme and 50% probability displacement ellipsoids.
	Fig. 3. Packing diagram of (I), viewed along the c axis. Dashed lines indicate O—H···N intramolecular interactions in molecules A & B.

11-[3-(Dimethylamino)propyl]-6,11-dihydrodibenzo[b,e]thiepin- 11-ol top

Crystal data top

C₁₉H₂₃NOS	F(000) = 1344
M_r = 313.44	D_x = 1.262 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 6805 reflections
a = 7.7215 (4) Å	θ = 4.3–74.0°
b = 15.3729 (10) Å	µ = 1.74 mm⁻¹
c = 27.9274 (16) Å	T = 110 K
β = 95.401 (6)°	Plate, colorless
V = 3300.3 (3) Å³	0.51 × 0.42 × 0.14 mm
Z = 8

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector	6565 independent reflections
Radiation source: Enhance (Cu) X-ray Source	5490 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 10.5081 pixels mm^-1	θ_max = 74.2°, θ_min = 4.3°
ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −13→19
T_min = 0.432, T_max = 1.000	l = −17→34
14666 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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.153	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.1079P)² + 0.6589P] where P = (F_o² + 2F_c²)/3
6565 reflections	(Δ/σ)_max = 0.001
403 parameters	Δρ_max = 0.58 e Å⁻³
0 restraints	Δρ_min = −0.56 e Å⁻³

Crystal data top

C₁₉H₂₃NOS	V = 3300.3 (3) Å³
M_r = 313.44	Z = 8
Monoclinic, P2₁/n	Cu Kα radiation
a = 7.7215 (4) Å	µ = 1.74 mm⁻¹
b = 15.3729 (10) Å	T = 110 K
c = 27.9274 (16) Å	0.51 × 0.42 × 0.14 mm
β = 95.401 (6)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector	6565 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	5490 reflections with I > 2σ(I)
T_min = 0.432, T_max = 1.000	R_int = 0.029
14666 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.153	H-atom parameters constrained
S = 1.05	Δρ_max = 0.58 e Å⁻³
6565 reflections	Δρ_min = −0.56 e Å⁻³
403 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
S1A	0.69626 (7)	0.25999 (3)	0.288172 (19)	0.02978 (15)
O1A	0.91923 (17)	0.54941 (9)	0.28401 (5)	0.0240 (3)
H1A	1.0075	0.5603	0.2696	0.029*
N1A	1.2061 (2)	0.56334 (11)	0.23664 (6)	0.0242 (4)
C1A	0.7385 (2)	0.44069 (13)	0.31337 (6)	0.0189 (4)
C2A	0.6889 (2)	0.50798 (13)	0.34289 (6)	0.0230 (4)
H2AA	0.7418	0.5635	0.3408	0.028*
C3A	0.5643 (3)	0.49613 (15)	0.37524 (7)	0.0276 (4)
H3AA	0.5350	0.5429	0.3952	0.033*
C4A	0.4833 (3)	0.41658 (15)	0.37828 (7)	0.0284 (4)
H4AA	0.3984	0.4079	0.4003	0.034*
C5A	0.5275 (3)	0.34982 (14)	0.34876 (7)	0.0264 (4)
H5AA	0.4697	0.2955	0.3502	0.032*
C6A	0.6554 (2)	0.35985 (13)	0.31669 (6)	0.0202 (4)
C7A	0.7862 (3)	0.28132 (13)	0.23129 (7)	0.0238 (4)
H7AA	0.9147	0.2814	0.2370	0.029*
H7AB	0.7527	0.2330	0.2089	0.029*
C8A	0.7295 (2)	0.36527 (13)	0.20746 (6)	0.0202 (4)
C9A	0.6275 (3)	0.36079 (15)	0.16343 (7)	0.0280 (4)
H9AA	0.5927	0.3055	0.1508	0.034*
C10A	0.5764 (3)	0.43455 (17)	0.13802 (7)	0.0331 (5)
H10A	0.5075	0.4301	0.1081	0.040*
C11A	0.6263 (3)	0.51514 (16)	0.15646 (7)	0.0306 (5)
H11A	0.5926	0.5665	0.1391	0.037*
C12A	0.7258 (2)	0.52091 (13)	0.20050 (7)	0.0232 (4)
H12A	0.7588	0.5766	0.2129	0.028*
C13A	0.7782 (2)	0.44720 (12)	0.22683 (6)	0.0170 (4)
C14A	0.8737 (2)	0.46053 (12)	0.27754 (6)	0.0181 (4)
C15A	1.0403 (2)	0.40533 (13)	0.28923 (6)	0.0207 (4)
H15A	1.1021	0.4278	0.3194	0.025*
H15B	1.0046	0.3448	0.2955	0.025*
C16A	1.1698 (2)	0.40312 (13)	0.25052 (7)	0.0218 (4)
H16A	1.2402	0.3494	0.2550	0.026*
H16B	1.1027	0.3994	0.2186	0.026*
C17A	1.2933 (2)	0.48049 (13)	0.25020 (7)	0.0241 (4)
H17A	1.3558	0.4868	0.2826	0.029*
H17B	1.3810	0.4683	0.2274	0.029*
C18A	1.1570 (3)	0.56816 (15)	0.18463 (7)	0.0296 (5)
H18A	1.0974	0.6234	0.1769	0.044*
H18B	1.0791	0.5197	0.1748	0.044*
H18C	1.2618	0.5646	0.1675	0.044*
C19A	1.3169 (3)	0.63736 (16)	0.25201 (10)	0.0396 (6)
H19A	1.2540	0.6917	0.2442	0.059*
H19B	1.4230	0.6358	0.2353	0.059*
H19C	1.3477	0.6342	0.2868	0.059*
S1B	0.66729 (7)	0.22246 (4)	0.627252 (18)	0.03356 (16)
O1B	0.39362 (17)	0.32974 (9)	0.47928 (5)	0.0224 (3)
H1B	0.2941	0.3119	0.4691	0.027*
N1B	0.0713 (2)	0.27183 (13)	0.45327 (6)	0.0272 (4)
C1B	0.6076 (2)	0.33566 (12)	0.54588 (6)	0.0194 (4)
C2B	0.6575 (2)	0.41167 (13)	0.52343 (7)	0.0225 (4)
H2BA	0.5966	0.4284	0.4937	0.027*
C3B	0.7936 (3)	0.46361 (14)	0.54324 (8)	0.0269 (4)
H3BA	0.8237	0.5154	0.5274	0.032*
C4B	0.8849 (3)	0.43913 (14)	0.58631 (8)	0.0296 (5)
H4BA	0.9773	0.4743	0.6003	0.036*
C5B	0.8406 (3)	0.36365 (14)	0.60857 (7)	0.0279 (4)
H5BA	0.9048	0.3467	0.6378	0.033*
C6B	0.7032 (2)	0.31114 (13)	0.58920 (7)	0.0227 (4)
C7B	0.5684 (3)	0.13299 (14)	0.59244 (7)	0.0292 (4)
H7BA	0.6145	0.0780	0.6070	0.035*
H7BB	0.4418	0.1340	0.5955	0.035*
C8B	0.5951 (2)	0.13126 (13)	0.53919 (7)	0.0249 (4)
C9B	0.6839 (3)	0.05921 (14)	0.52276 (9)	0.0340 (5)
H9BA	0.7316	0.0173	0.5453	0.041*
C10B	0.7035 (3)	0.04778 (15)	0.47439 (10)	0.0382 (6)
H10B	0.7637	−0.0015	0.4638	0.046*
C11B	0.6349 (3)	0.10843 (16)	0.44183 (8)	0.0341 (5)
H11B	0.6440	0.1002	0.4084	0.041*
C12B	0.5524 (2)	0.18169 (14)	0.45762 (7)	0.0257 (4)
H12B	0.5087	0.2240	0.4348	0.031*
C13B	0.5316 (2)	0.19501 (13)	0.50640 (7)	0.0199 (4)
C14B	0.4538 (2)	0.28306 (12)	0.52111 (6)	0.0187 (4)
C15B	0.3036 (2)	0.27781 (14)	0.55385 (7)	0.0231 (4)
H15C	0.3525	0.2592	0.5863	0.028*
H15D	0.2554	0.3370	0.5570	0.028*
C16B	0.1534 (2)	0.21639 (14)	0.53708 (7)	0.0258 (4)
H16C	0.2030	0.1642	0.5227	0.031*
H16D	0.0976	0.1970	0.5657	0.031*
C17B	0.0125 (2)	0.25346 (13)	0.50080 (7)	0.0220 (4)
H17C	−0.0853	0.2116	0.4968	0.026*
H17D	−0.0321	0.3080	0.5140	0.026*
C18B	0.0944 (3)	0.1914 (2)	0.42672 (9)	0.0515 (8)
H18D	0.1890	0.1573	0.4433	0.077*
H18E	0.1232	0.2054	0.3942	0.077*
H18F	−0.0136	0.1575	0.4248	0.077*
C19B	−0.0530 (3)	0.3298 (2)	0.42629 (9)	0.0479 (7)
H19D	−0.0118	0.3430	0.3950	0.072*
H19E	−0.0635	0.3839	0.4444	0.072*
H19F	−0.1668	0.3012	0.4215	0.072*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1A	0.0386 (3)	0.0189 (2)	0.0344 (3)	−0.0007 (2)	0.0165 (2)	0.00348 (19)
O1A	0.0191 (7)	0.0210 (7)	0.0333 (7)	−0.0042 (5)	0.0094 (5)	−0.0068 (6)
N1A	0.0208 (8)	0.0233 (8)	0.0293 (8)	−0.0028 (6)	0.0070 (6)	−0.0039 (7)
C1A	0.0150 (8)	0.0269 (9)	0.0148 (8)	0.0016 (7)	0.0015 (6)	0.0003 (7)
C2A	0.0194 (9)	0.0291 (10)	0.0208 (8)	0.0002 (7)	0.0025 (7)	−0.0039 (8)
C3A	0.0247 (10)	0.0398 (12)	0.0188 (8)	0.0059 (9)	0.0047 (7)	−0.0055 (8)
C4A	0.0240 (10)	0.0434 (12)	0.0189 (8)	0.0055 (9)	0.0078 (7)	0.0078 (8)
C5A	0.0249 (10)	0.0315 (11)	0.0234 (9)	0.0026 (8)	0.0059 (7)	0.0092 (8)
C6A	0.0209 (9)	0.0222 (9)	0.0177 (8)	0.0033 (7)	0.0022 (7)	0.0030 (7)
C7A	0.0269 (10)	0.0198 (9)	0.0258 (9)	0.0003 (7)	0.0088 (7)	−0.0037 (7)
C8A	0.0184 (9)	0.0251 (10)	0.0177 (8)	−0.0006 (7)	0.0051 (7)	−0.0007 (7)
C9A	0.0237 (10)	0.0395 (12)	0.0210 (9)	−0.0004 (9)	0.0031 (7)	−0.0090 (8)
C10A	0.0236 (10)	0.0594 (15)	0.0164 (8)	0.0080 (10)	0.0018 (7)	0.0004 (9)
C11A	0.0210 (10)	0.0468 (13)	0.0254 (9)	0.0101 (9)	0.0091 (7)	0.0159 (9)
C12A	0.0166 (8)	0.0265 (10)	0.0277 (9)	0.0028 (7)	0.0089 (7)	0.0068 (8)
C13A	0.0121 (8)	0.0230 (9)	0.0169 (8)	0.0016 (7)	0.0065 (6)	0.0015 (7)
C14A	0.0166 (8)	0.0192 (9)	0.0190 (8)	−0.0008 (7)	0.0041 (6)	−0.0021 (7)
C15A	0.0168 (8)	0.0257 (10)	0.0198 (8)	0.0013 (7)	0.0026 (6)	−0.0003 (7)
C16A	0.0171 (9)	0.0246 (9)	0.0242 (9)	0.0036 (7)	0.0049 (7)	0.0001 (7)
C17A	0.0160 (8)	0.0306 (10)	0.0260 (9)	0.0008 (8)	0.0033 (7)	−0.0002 (8)
C18A	0.0264 (10)	0.0345 (11)	0.0293 (10)	0.0043 (8)	0.0103 (8)	0.0074 (9)
C19A	0.0314 (12)	0.0322 (12)	0.0572 (14)	−0.0121 (10)	0.0155 (11)	−0.0117 (11)
S1B	0.0336 (3)	0.0426 (3)	0.0233 (3)	0.0001 (2)	−0.00317 (19)	0.0080 (2)
O1B	0.0184 (6)	0.0281 (7)	0.0199 (6)	−0.0033 (5)	−0.0022 (5)	0.0059 (5)
N1B	0.0221 (8)	0.0414 (10)	0.0180 (7)	−0.0099 (7)	0.0010 (6)	0.0005 (7)
C1B	0.0158 (8)	0.0226 (9)	0.0200 (8)	0.0041 (7)	0.0026 (7)	−0.0039 (7)
C2B	0.0179 (9)	0.0246 (9)	0.0248 (9)	0.0030 (7)	0.0018 (7)	−0.0044 (8)
C3B	0.0213 (9)	0.0237 (9)	0.0357 (10)	0.0016 (8)	0.0033 (8)	−0.0048 (8)
C4B	0.0206 (9)	0.0308 (11)	0.0362 (11)	0.0004 (8)	−0.0034 (8)	−0.0133 (9)
C5B	0.0222 (10)	0.0354 (11)	0.0250 (9)	0.0063 (8)	−0.0038 (7)	−0.0070 (8)
C6B	0.0213 (9)	0.0254 (9)	0.0212 (8)	0.0062 (7)	0.0014 (7)	−0.0019 (8)
C7B	0.0353 (11)	0.0253 (10)	0.0283 (10)	−0.0100 (9)	0.0094 (8)	0.0047 (8)
C8B	0.0171 (9)	0.0241 (10)	0.0336 (10)	−0.0039 (7)	0.0027 (7)	0.0009 (8)
C9B	0.0218 (10)	0.0223 (10)	0.0581 (14)	−0.0020 (8)	0.0040 (9)	0.0019 (10)
C10B	0.0218 (10)	0.0288 (11)	0.0657 (16)	−0.0039 (9)	0.0135 (10)	−0.0190 (11)
C11B	0.0229 (10)	0.0411 (12)	0.0403 (11)	−0.0105 (9)	0.0127 (9)	−0.0188 (10)
C12B	0.0175 (9)	0.0341 (11)	0.0264 (9)	−0.0067 (8)	0.0061 (7)	−0.0057 (8)
C13B	0.0117 (8)	0.0243 (9)	0.0241 (9)	−0.0032 (7)	0.0045 (6)	−0.0036 (7)
C14B	0.0169 (9)	0.0228 (9)	0.0163 (8)	0.0010 (7)	0.0014 (6)	0.0015 (7)
C15B	0.0168 (9)	0.0341 (10)	0.0184 (8)	0.0037 (8)	0.0022 (7)	0.0015 (8)
C16B	0.0178 (9)	0.0327 (11)	0.0274 (9)	−0.0008 (8)	0.0048 (7)	0.0102 (8)
C17B	0.0169 (9)	0.0289 (10)	0.0206 (8)	−0.0005 (7)	0.0038 (7)	−0.0008 (7)
C18B	0.0343 (13)	0.079 (2)	0.0434 (13)	−0.0256 (13)	0.0172 (11)	−0.0361 (14)
C19B	0.0280 (12)	0.0747 (19)	0.0382 (12)	−0.0149 (12)	−0.0115 (9)	0.0277 (13)

Geometric parameters (Å, º) top

S1A—C6A	1.7713 (19)	S1B—C6B	1.766 (2)
S1A—C7A	1.822 (2)	S1B—C7B	1.811 (2)
O1A—C14A	1.418 (2)	O1B—C14B	1.412 (2)
O1A—H1A	0.8400	O1B—H1B	0.8400
N1A—C19A	1.463 (3)	N1B—C18B	1.461 (3)
N1A—C18A	1.468 (3)	N1B—C19B	1.465 (3)
N1A—C17A	1.473 (3)	N1B—C17B	1.470 (2)
C1A—C2A	1.398 (3)	C1B—C2B	1.397 (3)
C1A—C6A	1.406 (3)	C1B—C6B	1.408 (2)
C1A—C14A	1.543 (2)	C1B—C14B	1.545 (2)
C2A—C3A	1.393 (3)	C2B—C3B	1.393 (3)
C2A—H2AA	0.9500	C2B—H2BA	0.9500
C3A—C4A	1.380 (3)	C3B—C4B	1.388 (3)
C3A—H3AA	0.9500	C3B—H3BA	0.9500
C4A—C5A	1.380 (3)	C4B—C5B	1.375 (3)
C4A—H4AA	0.9500	C4B—H4BA	0.9500
C5A—C6A	1.402 (3)	C5B—C6B	1.401 (3)
C5A—H5AA	0.9500	C5B—H5BA	0.9500
C7A—C8A	1.498 (3)	C7B—C8B	1.521 (3)
C7A—H7AA	0.9900	C7B—H7BA	0.9900
C7A—H7AB	0.9900	C7B—H7BB	0.9900
C8A—C9A	1.398 (3)	C8B—C13B	1.398 (3)
C8A—C13A	1.408 (3)	C8B—C9B	1.402 (3)
C9A—C10A	1.376 (3)	C9B—C10B	1.384 (4)
C9A—H9AA	0.9500	C9B—H9BA	0.9500
C10A—C11A	1.382 (3)	C10B—C11B	1.373 (4)
C10A—H10A	0.9500	C10B—H10B	0.9500
C11A—C12A	1.390 (3)	C11B—C12B	1.386 (3)
C11A—H11A	0.9500	C11B—H11B	0.9500
C12A—C13A	1.390 (3)	C12B—C13B	1.402 (3)
C12A—H12A	0.9500	C12B—H12B	0.9500
C13A—C14A	1.548 (2)	C13B—C14B	1.552 (3)
C14A—C15A	1.550 (2)	C14B—C15B	1.545 (2)
C15A—C16A	1.540 (2)	C15B—C16B	1.534 (3)
C15A—H15A	0.9900	C15B—H15C	0.9900
C15A—H15B	0.9900	C15B—H15D	0.9900
C16A—C17A	1.525 (3)	C16B—C17B	1.525 (3)
C16A—H16A	0.9900	C16B—H16C	0.9900
C16A—H16B	0.9900	C16B—H16D	0.9900
C17A—H17A	0.9900	C17B—H17C	0.9900
C17A—H17B	0.9900	C17B—H17D	0.9900
C18A—H18A	0.9800	C18B—H18D	0.9800
C18A—H18B	0.9800	C18B—H18E	0.9800
C18A—H18C	0.9800	C18B—H18F	0.9800
C19A—H19A	0.9800	C19B—H19D	0.9800
C19A—H19B	0.9800	C19B—H19E	0.9800
C19A—H19C	0.9800	C19B—H19F	0.9800

C6A—S1A—C7A	109.55 (9)	C6B—S1B—C7B	110.20 (9)
C14A—O1A—H1A	109.5	C14B—O1B—H1B	109.5
C19A—N1A—C18A	109.89 (18)	C18B—N1B—C19B	111.0 (2)
C19A—N1A—C17A	110.88 (17)	C18B—N1B—C17B	111.00 (19)
C18A—N1A—C17A	111.53 (16)	C19B—N1B—C17B	109.77 (18)
C2A—C1A—C6A	117.58 (17)	C2B—C1B—C6B	117.73 (17)
C2A—C1A—C14A	118.41 (17)	C2B—C1B—C14B	118.00 (15)
C6A—C1A—C14A	123.95 (16)	C6B—C1B—C14B	124.27 (17)
C3A—C2A—C1A	122.01 (19)	C3B—C2B—C1B	122.07 (18)
C3A—C2A—H2AA	119.0	C3B—C2B—H2BA	119.0
C1A—C2A—H2AA	119.0	C1B—C2B—H2BA	119.0
C4A—C3A—C2A	120.05 (19)	C4B—C3B—C2B	119.4 (2)
C4A—C3A—H3AA	120.0	C4B—C3B—H3BA	120.3
C2A—C3A—H3AA	120.0	C2B—C3B—H3BA	120.3
C5A—C4A—C3A	118.91 (18)	C5B—C4B—C3B	119.56 (19)
C5A—C4A—H4AA	120.5	C5B—C4B—H4BA	120.2
C3A—C4A—H4AA	120.5	C3B—C4B—H4BA	120.2
C4A—C5A—C6A	121.9 (2)	C4B—C5B—C6B	121.55 (18)
C4A—C5A—H5AA	119.0	C4B—C5B—H5BA	119.2
C6A—C5A—H5AA	119.0	C6B—C5B—H5BA	119.2
C5A—C6A—C1A	119.50 (18)	C5B—C6B—C1B	119.62 (19)
C5A—C6A—S1A	110.96 (15)	C5B—C6B—S1B	111.62 (14)
C1A—C6A—S1A	129.40 (14)	C1B—C6B—S1B	128.64 (16)
C8A—C7A—S1A	115.01 (13)	C8B—C7B—S1B	116.69 (14)
C8A—C7A—H7AA	108.5	C8B—C7B—H7BA	108.1
S1A—C7A—H7AA	108.5	S1B—C7B—H7BA	108.1
C8A—C7A—H7AB	108.5	C8B—C7B—H7BB	108.1
S1A—C7A—H7AB	108.5	S1B—C7B—H7BB	108.1
H7AA—C7A—H7AB	107.5	H7BA—C7B—H7BB	107.3
C9A—C8A—C13A	119.34 (18)	C13B—C8B—C9B	119.4 (2)
C9A—C8A—C7A	117.71 (18)	C13B—C8B—C7B	123.82 (18)
C13A—C8A—C7A	122.93 (16)	C9B—C8B—C7B	116.7 (2)
C10A—C9A—C8A	121.6 (2)	C10B—C9B—C8B	121.4 (2)
C10A—C9A—H9AA	119.2	C10B—C9B—H9BA	119.3
C8A—C9A—H9AA	119.2	C8B—C9B—H9BA	119.3
C9A—C10A—C11A	119.35 (18)	C11B—C10B—C9B	119.3 (2)
C9A—C10A—H10A	120.3	C11B—C10B—H10B	120.3
C11A—C10A—H10A	120.3	C9B—C10B—H10B	120.3
C10A—C11A—C12A	119.9 (2)	C10B—C11B—C12B	120.1 (2)
C10A—C11A—H11A	120.1	C10B—C11B—H11B	120.0
C12A—C11A—H11A	120.1	C12B—C11B—H11B	120.0
C13A—C12A—C11A	121.7 (2)	C11B—C12B—C13B	121.7 (2)
C13A—C12A—H12A	119.2	C11B—C12B—H12B	119.1
C11A—C12A—H12A	119.2	C13B—C12B—H12B	119.1
C12A—C13A—C8A	118.18 (17)	C8B—C13B—C12B	117.96 (18)
C12A—C13A—C14A	117.78 (17)	C8B—C13B—C14B	123.96 (16)
C8A—C13A—C14A	123.85 (16)	C12B—C13B—C14B	117.86 (17)
O1A—C14A—C1A	106.40 (14)	O1B—C14B—C1B	106.49 (15)
O1A—C14A—C13A	109.58 (15)	O1B—C14B—C15B	108.00 (14)
C1A—C14A—C13A	105.90 (14)	C1B—C14B—C15B	110.53 (14)
O1A—C14A—C15A	108.06 (14)	O1B—C14B—C13B	109.25 (14)
C1A—C14A—C15A	110.73 (14)	C1B—C14B—C13B	105.96 (14)
C13A—C14A—C15A	115.78 (14)	C15B—C14B—C13B	116.21 (16)
C16A—C15A—C14A	116.41 (15)	C16B—C15B—C14B	116.08 (16)
C16A—C15A—H15A	108.2	C16B—C15B—H15C	108.3
C14A—C15A—H15A	108.2	C14B—C15B—H15C	108.3
C16A—C15A—H15B	108.2	C16B—C15B—H15D	108.3
C14A—C15A—H15B	108.2	C14B—C15B—H15D	108.3
H15A—C15A—H15B	107.3	H15C—C15B—H15D	107.4
C17A—C16A—C15A	115.75 (16)	C17B—C16B—C15B	116.37 (17)
C17A—C16A—H16A	108.3	C17B—C16B—H16C	108.2
C15A—C16A—H16A	108.3	C15B—C16B—H16C	108.2
C17A—C16A—H16B	108.3	C17B—C16B—H16D	108.2
C15A—C16A—H16B	108.3	C15B—C16B—H16D	108.2
H16A—C16A—H16B	107.4	H16C—C16B—H16D	107.3
N1A—C17A—C16A	113.87 (15)	N1B—C17B—C16B	114.20 (16)
N1A—C17A—H17A	108.8	N1B—C17B—H17C	108.7
C16A—C17A—H17A	108.8	C16B—C17B—H17C	108.7
N1A—C17A—H17B	108.8	N1B—C17B—H17D	108.7
C16A—C17A—H17B	108.8	C16B—C17B—H17D	108.7
H17A—C17A—H17B	107.7	H17C—C17B—H17D	107.6
N1A—C18A—H18A	109.5	N1B—C18B—H18D	109.5
N1A—C18A—H18B	109.5	N1B—C18B—H18E	109.5
H18A—C18A—H18B	109.5	H18D—C18B—H18E	109.5
N1A—C18A—H18C	109.5	N1B—C18B—H18F	109.5
H18A—C18A—H18C	109.5	H18D—C18B—H18F	109.5
H18B—C18A—H18C	109.5	H18E—C18B—H18F	109.5
N1A—C19A—H19A	109.5	N1B—C19B—H19D	109.5
N1A—C19A—H19B	109.5	N1B—C19B—H19E	109.5
H19A—C19A—H19B	109.5	H19D—C19B—H19E	109.5
N1A—C19A—H19C	109.5	N1B—C19B—H19F	109.5
H19A—C19A—H19C	109.5	H19D—C19B—H19F	109.5
H19B—C19A—H19C	109.5	H19E—C19B—H19F	109.5

C6A—C1A—C2A—C3A	1.2 (3)	C6B—C1B—C2B—C3B	−1.7 (3)
C14A—C1A—C2A—C3A	178.23 (17)	C14B—C1B—C2B—C3B	179.50 (17)
C1A—C2A—C3A—C4A	−1.2 (3)	C1B—C2B—C3B—C4B	0.8 (3)
C2A—C3A—C4A—C5A	−0.2 (3)	C2B—C3B—C4B—C5B	0.6 (3)
C3A—C4A—C5A—C6A	1.6 (3)	C3B—C4B—C5B—C6B	−1.0 (3)
C4A—C5A—C6A—C1A	−1.6 (3)	C4B—C5B—C6B—C1B	0.1 (3)
C4A—C5A—C6A—S1A	174.51 (16)	C4B—C5B—C6B—S1B	−176.25 (16)
C2A—C1A—C6A—C5A	0.2 (3)	C2B—C1B—C6B—C5B	1.2 (3)
C14A—C1A—C6A—C5A	−176.66 (16)	C14B—C1B—C6B—C5B	179.94 (17)
C2A—C1A—C6A—S1A	−175.12 (14)	C2B—C1B—C6B—S1B	176.89 (15)
C14A—C1A—C6A—S1A	8.0 (3)	C14B—C1B—C6B—S1B	−4.4 (3)
C7A—S1A—C6A—C5A	156.28 (14)	C7B—S1B—C6B—C5B	−153.88 (15)
C7A—S1A—C6A—C1A	−28.0 (2)	C7B—S1B—C6B—C1B	30.1 (2)
C6A—S1A—C7A—C8A	−29.24 (17)	C6B—S1B—C7B—C8B	22.7 (2)
S1A—C7A—C8A—C9A	−114.43 (17)	S1B—C7B—C8B—C13B	−63.9 (2)
S1A—C7A—C8A—C13A	67.3 (2)	S1B—C7B—C8B—C9B	118.40 (19)
C13A—C8A—C9A—C10A	1.4 (3)	C13B—C8B—C9B—C10B	−2.9 (3)
C7A—C8A—C9A—C10A	−176.99 (18)	C7B—C8B—C9B—C10B	174.94 (19)
C8A—C9A—C10A—C11A	−0.3 (3)	C8B—C9B—C10B—C11B	0.2 (3)
C9A—C10A—C11A—C12A	−0.6 (3)	C9B—C10B—C11B—C12B	2.2 (3)
C10A—C11A—C12A—C13A	0.3 (3)	C10B—C11B—C12B—C13B	−1.9 (3)
C11A—C12A—C13A—C8A	0.7 (3)	C9B—C8B—C13B—C12B	3.1 (3)
C11A—C12A—C13A—C14A	−174.38 (16)	C7B—C8B—C13B—C12B	−174.58 (17)
C9A—C8A—C13A—C12A	−1.6 (3)	C9B—C8B—C13B—C14B	−171.44 (17)
C7A—C8A—C13A—C12A	176.71 (17)	C7B—C8B—C13B—C14B	10.9 (3)
C9A—C8A—C13A—C14A	173.24 (17)	C11B—C12B—C13B—C8B	−0.7 (3)
C7A—C8A—C13A—C14A	−8.5 (3)	C11B—C12B—C13B—C14B	174.11 (17)
C2A—C1A—C14A—O1A	0.3 (2)	C2B—C1B—C14B—O1B	−1.8 (2)
C6A—C1A—C14A—O1A	177.21 (16)	C6B—C1B—C14B—O1B	179.50 (16)
C2A—C1A—C14A—C13A	−116.21 (17)	C2B—C1B—C14B—C15B	−118.81 (18)
C6A—C1A—C14A—C13A	60.7 (2)	C6B—C1B—C14B—C15B	62.4 (2)
C2A—C1A—C14A—C15A	117.54 (18)	C2B—C1B—C14B—C13B	114.50 (18)
C6A—C1A—C14A—C15A	−65.6 (2)	C6B—C1B—C14B—C13B	−64.2 (2)
C12A—C13A—C14A—O1A	−11.1 (2)	C8B—C13B—C14B—O1B	−176.78 (16)
C8A—C13A—C14A—O1A	174.06 (15)	C12B—C13B—C14B—O1B	8.7 (2)
C12A—C13A—C14A—C1A	103.27 (18)	C8B—C13B—C14B—C1B	68.8 (2)
C8A—C13A—C14A—C1A	−71.5 (2)	C12B—C13B—C14B—C1B	−105.66 (18)
C12A—C13A—C14A—C15A	−133.61 (17)	C8B—C13B—C14B—C15B	−54.3 (2)
C8A—C13A—C14A—C15A	51.6 (2)	C12B—C13B—C14B—C15B	131.16 (17)
O1A—C14A—C15A—C16A	−76.66 (19)	O1B—C14B—C15B—C16B	72.5 (2)
C1A—C14A—C15A—C16A	167.18 (15)	C1B—C14B—C15B—C16B	−171.34 (16)
C13A—C14A—C15A—C16A	46.6 (2)	C13B—C14B—C15B—C16B	−50.6 (2)
C14A—C15A—C16A—C17A	81.9 (2)	C14B—C15B—C16B—C17B	−84.3 (2)
C19A—N1A—C17A—C16A	161.24 (17)	C18B—N1B—C17B—C16B	73.7 (2)
C18A—N1A—C17A—C16A	−75.9 (2)	C19B—N1B—C17B—C16B	−163.21 (19)
C15A—C16A—C17A—N1A	−66.7 (2)	C15B—C16B—C17B—N1B	67.5 (2)

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2, Cg7 and Cg8 are the centroids of the C1A—C6A, C8A—C13A, C1B–C6B and C8B—C13B rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···N1A	0.84	1.86	2.693 (2)	170
O1B—H1B···N1B	0.84	1.84	2.679 (2)	174
C4A—H4AA···O1B	0.95	2.51	3.253 (2)	135
C3A—H3AA···Cg7ⁱ	0.95	2.74	3.526 (6)	140
C17A—H17A···Cg1ⁱⁱ	0.99	2.67	3.537 (7)	147
C17A—H17B···Cg2ⁱⁱ	0.99	2.75	3.720 (3)	167
C17B—H17C···Cg8ⁱⁱⁱ	0.99	2.68	3.663 (6)	170
C17B—17D···Cg7ⁱⁱⁱ	0.99	2.64	3.538 (1)	149

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y, z; (iii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₃NOS
M_r	313.44
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	110
a, b, c (Å)	7.7215 (4), 15.3729 (10), 27.9274 (16)
β (°)	95.401 (6)
V (Å³)	3300.3 (3)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	1.74
Crystal size (mm)	0.51 × 0.42 × 0.14

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2007)
T_min, T_max	0.432, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	14666, 6565, 5490
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.624

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.153, 1.05
No. of reflections	6565
No. of parameters	403
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.56

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2, Cg7 and Cg8 are the centroids of the C1A—C6A, C8A—C13A, C1B–C6B and C8B—C13B rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···N1A	0.84	1.86	2.693 (2)	169.9
O1B—H1B···N1B	0.84	1.84	2.679 (2)	174.1
C4A—H4AA···O1B	0.95	2.51	3.253 (2)	134.7
C3A—H3AA···Cg7ⁱ	0.95	2.74	3.526 (6)	140
C17A—H17A···Cg1ⁱⁱ	0.99	2.67	3.537 (7)	147
C17A—H17B···Cg2ⁱⁱ	0.99	2.75	3.720 (3)	167
C17B—H17C···Cg8ⁱⁱⁱ	0.99	2.68	3.663 (6)	170
C17B—17D···Cg7ⁱⁱⁱ	0.99	2.64	3.538 (1)	149

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y, z; (iii) x−1, y, z.

Acknowledgements

QNMHA thanks the University of Mysore for use of their research facilities. RJB acknowledges the NSF MRI program (Grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.

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