9-[3-(Dimethyl­amino)­prop­yl]-2-trifluoro­meth­yl-9H-thioxanthen-9-ol

Jasinski, J.P.; Golen, J.A.; Siddegowda, M.S.; Yathirajan, H.S.; Swamy, M.T.

doi:10.1107/S1600536811025311

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o1883

doi:10.1107/S1600536811025311

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9-[3-(Dimethylamino)propyl]-2-trifluoromethyl-9H-thioxanthen-9-ol

Jerry P. Jasinski,^a ^* James A. Golen,^a M. S. Siddegowda,^b H. S. Yathirajan ^b and M. T. Swamy ^c

^aDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, ^bDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and ^cDepartment of Chemistry, Sambhram Institute of Technology, Bangalore 560 097, India
^*Correspondence e-mail: jjasinski@keene.edu

(Received 23 June 2011; accepted 27 June 2011; online 2 July 2011)

In the title compound, C₁₉H₂₀F₃NOS, the dihedral angle between the mean planes of the two benzene rings attached to the thioxanthene ring is 41.8 (7)°; the latter has a slightly distorted boat conformation. The F atoms are disordered over three sets of sites [occupancy ratio = 0.564 (10):0.287 (10):0.148 (5)] and the methyl groups are disordered over two sets of sites [occupancy ratio = 0.72 (4):0.28 (4)]. The crystal packing is stabilized by O—H⋯N and C—H⋯S hydrogen bonds and weak C—H⋯Cg interactions.

Related literature

For photo-initiators with excellent capabilities in UV-curing materials, see: Fouassier et al. (1995 ); Roffey (1997 ). For related structures, see: Post et al. (1975a ,b ); Liu, (2009 ). For puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₉H₂₀F₃NOS
M_r = 367.42
Monoclinic, P 2₁ /n
a = 7.6183 (3) Å
b = 13.9605 (4) Å
c = 17.4172 (7) Å
β = 101.053 (4)°
V = 1818.05 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 170 K
0.35 × 0.33 × 0.30 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.929, T_max = 0.939
17330 measured reflections
4697 independent reflections
3901 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.116
S = 1.05
4697 reflections
306 parameters
238 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C2–C7 and C8–C13 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1	0.87 (2)	1.84 (2)	2.7141 (17)	176 (2)
C15—H15A⋯S1	0.99	2.76	3.4165 (15)	124
C5—H5A⋯Cg3ⁱ	0.95	2.96	3.798 (3)	148
C17—H17A⋯Cg2ⁱⁱ	0.99	2.97	3.949 (3)	170
C17—H17B⋯Cg3ⁱⁱ	0.99	2.83	3.659 (3)	142
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x-1, y, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811025311/tk2761sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811025311/tk2761Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811025311/tk2761Isup3.cml

checkCIF report

Comment top

The title compound is a flupenthixol impurity with systematic IUPAC name: (RS)-9-[3-(dimethylamino)propyl]-2-(trifluoromethyl)-9H-thioxanthen-9-ol. Flupenthixol is a thioxanthene derivative that may exist in two isomeric forms, α and β. Flupenthixol contains 45-55 % α-flupenthixol. The pharmacological effects of flupenthixol, α- and β-flupenthixol have been compared with those of clopenthixol, chlorprothixene, fluphenazine, perphenazine, chlorpromazine and haloperidol. In most pharmacological screening tests α-flupenthixol was equipotent with fluphenazine. β-Flupenthixol showed very low pharmacological activity. As expected the potency of flupenthixol was about one half that of α-flupenthixol. Thioxanthone derivatives are good photoinitiators with excellent capabilities in UV-curing materials (Fouassier et al., 1995; Roffey, 1997). The crystal structures of α-flupenthixol (Post et al., 1975b), β-flupenthixol (Post et al., 1975a) and 2,4-diethylthioxanthen-9-one (Liu, 2009) have been reported. In view of the importance of the title compound the crystal structure is herein reported.

In the title compound, (I), the dihedral angle between the mean planes of the two benzene rings in the thioxanthene ring is 41.8 (7) ° (Fig. 1). The thioxanthene ring is in a slightly distorted boat conformation (Cremer & Pople, 1975) with puckering parameters Q, θ, and ϕ = 0.591 (2) Å, 92.72 (19) ° and 359.8 (2) °, respectively). Crystal packing is stabilized by O1—H1A···N1, C15—H15A···S1 hydrogen bonds and weak C—H···Cg intermolecular interactions (Fig. 2, Table 1).

Related literature top

For photo-initiators with excellent capabilities in UV-curing materials, see: Fouassier et al. (1995); Roffey (1997). For related structures, see: Post et al. (1975a,b); Liu, (2009). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

The title compound was obtained as a gift sample from R. L. Fine Chem. Ltd., Bangalore, India. The compound was recrystallized from dichloromethane (M.pt.: 389–391 K).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis RED (Oxford Diffraction, 2010); 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 (I) showing the atom labeling scheme and 50% probability displacement ellipsoids.
	Fig. 2. Packing diagram of the title compound viewed down the a axis. Dashed lines represent disordered C—F atoms.

9-[3-(Dimethylamino)propyl]-2-trifluoromethyl-9H-thioxanthen-9-ol top

Crystal data top

C₁₉H₂₀F₃NOS	F(000) = 768
M_r = 367.42	D_x = 1.342 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9234 reflections
a = 7.6183 (3) Å	θ = 3.3–32.3°
b = 13.9605 (4) Å	µ = 0.21 mm⁻¹
c = 17.4172 (7) Å	T = 170 K
β = 101.053 (4)°	Block, pale yellow
V = 1818.05 (11) Å³	0.35 × 0.33 × 0.30 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur Eos Gemini diffractometer	4697 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3901 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
Detector resolution: 16.1500 pixels mm^-1	θ_max = 28.7°, θ_min = 3.5°
ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −18→15
T_min = 0.929, T_max = 0.939	l = −23→23
17330 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0506P)² + 0.6042P] where P = (F_o² + 2F_c²)/3
4697 reflections	(Δ/σ)_max = 0.037
306 parameters	Δρ_max = 0.28 e Å⁻³
238 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₉H₂₀F₃NOS	V = 1818.05 (11) Å³
M_r = 367.42	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.6183 (3) Å	µ = 0.21 mm⁻¹
b = 13.9605 (4) Å	T = 170 K
c = 17.4172 (7) Å	0.35 × 0.33 × 0.30 mm
β = 101.053 (4)°

Data collection top

Oxford Diffraction Xcalibur Eos Gemini diffractometer	4697 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	3901 reflections with I > 2σ(I)
T_min = 0.929, T_max = 0.939	R_int = 0.022
17330 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	238 restraints
wR(F²) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.28 e Å⁻³
4697 reflections	Δρ_min = −0.29 e Å⁻³
306 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	Occ. (<1)
S1	0.74858 (6)	0.83313 (3)	0.17618 (2)	0.04558 (12)
F1	0.6729 (8)	0.6443 (4)	0.5165 (2)	0.0783 (14)	0.564 (10)
F2	0.9343 (6)	0.5995 (5)	0.5119 (4)	0.0815 (15)	0.564 (10)
F3	0.7169 (10)	0.5137 (4)	0.4572 (4)	0.0765 (16)	0.564 (10)
F1A	0.6033 (13)	0.6017 (10)	0.4888 (7)	0.078 (2)	0.287 (10)
F2A	0.8891 (19)	0.6238 (7)	0.5244 (5)	0.072 (3)	0.287 (10)
F3A	0.7863 (16)	0.5067 (7)	0.4533 (7)	0.059 (2)	0.287 (10)
F1B	0.5941 (16)	0.5562 (12)	0.4648 (6)	0.070 (3)	0.148 (5)
F2B	0.785 (3)	0.6465 (10)	0.5293 (6)	0.075 (3)	0.148 (5)
F3B	0.864 (2)	0.5254 (12)	0.4705 (10)	0.091 (4)	0.148 (5)
O1	0.50685 (14)	0.54112 (7)	0.18448 (6)	0.0369 (2)
H1A	0.408 (3)	0.5332 (16)	0.2017 (13)	0.070 (6)*
N1	0.19359 (19)	0.52532 (10)	0.23591 (10)	0.0543 (4)
C1	0.54324 (17)	0.63994 (9)	0.17934 (8)	0.0316 (3)
C2	0.65553 (17)	0.67633 (9)	0.25587 (8)	0.0319 (3)
C3	0.66939 (18)	0.62297 (10)	0.32396 (8)	0.0346 (3)
H3A	0.6162	0.5612	0.3220	0.041*
C4	0.7599 (2)	0.65865 (11)	0.39484 (9)	0.0410 (3)
C5	0.8404 (2)	0.74815 (12)	0.39867 (10)	0.0501 (4)
H5A	0.8989	0.7732	0.4476	0.060*
C6	0.8350 (2)	0.80039 (12)	0.33140 (10)	0.0473 (4)
H6A	0.8935	0.8607	0.3334	0.057*
C7	0.74356 (18)	0.76466 (10)	0.26013 (9)	0.0363 (3)
C8	0.7353 (2)	0.74071 (11)	0.10656 (9)	0.0406 (3)
C9	0.8206 (3)	0.75615 (14)	0.04376 (11)	0.0562 (4)
H9A	0.8784	0.8155	0.0388	0.067*
C10	0.8210 (3)	0.68539 (17)	−0.01102 (12)	0.0683 (6)
H10A	0.8778	0.6962	−0.0543	0.082*
C11	0.7391 (3)	0.59858 (16)	−0.00345 (11)	0.0641 (5)
H11A	0.7412	0.5494	−0.0410	0.077*
C12	0.6541 (2)	0.58328 (13)	0.05899 (9)	0.0478 (4)
H12A	0.5992	0.5231	0.0642	0.057*
C13	0.64777 (18)	0.65429 (10)	0.11405 (8)	0.0363 (3)
C14	0.7655 (3)	0.60126 (14)	0.46712 (10)	0.0534 (4)
C15	0.36815 (18)	0.69875 (11)	0.15859 (9)	0.0411 (3)
H15A	0.4009	0.7658	0.1494	0.049*
H15B	0.2994	0.6740	0.1085	0.049*
C16	0.2439 (2)	0.69987 (11)	0.21787 (11)	0.0489 (4)
H16A	0.3181	0.6992	0.2712	0.059*
H16B	0.1758	0.7607	0.2119	0.059*
C17	0.1118 (2)	0.61725 (12)	0.21095 (12)	0.0525 (4)
H17A	0.0208	0.6320	0.2429	0.063*
H17B	0.0494	0.6119	0.1558	0.063*
C18	0.2274 (12)	0.5222 (12)	0.3225 (4)	0.095 (2)	0.72 (4)
H18A	0.3144	0.5718	0.3435	0.142*	0.72 (4)
H18B	0.2749	0.4591	0.3404	0.142*	0.72 (4)
H18C	0.1153	0.5336	0.3407	0.142*	0.72 (4)
C19	0.0843 (17)	0.4459 (7)	0.2028 (8)	0.100 (3)	0.72 (4)
H19A	0.0712	0.4470	0.1457	0.150*	0.72 (4)
H19B	−0.0339	0.4509	0.2169	0.150*	0.72 (4)
H19C	0.1412	0.3857	0.2232	0.150*	0.72 (4)
C18A	0.224 (3)	0.5017 (14)	0.3172 (8)	0.067 (4)	0.28 (4)
H18D	0.2296	0.4320	0.3234	0.101*	0.28 (4)
H18E	0.1268	0.5272	0.3406	0.101*	0.28 (4)
H18F	0.3380	0.5298	0.3435	0.101*	0.28 (4)
C19A	0.061 (2)	0.4530 (13)	0.1931 (10)	0.051 (4)	0.28 (4)
H19D	0.0576	0.4581	0.1367	0.076*	0.28 (4)
H19E	−0.0578	0.4659	0.2041	0.076*	0.28 (4)
H19F	0.0989	0.3882	0.2108	0.076*	0.28 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0509 (2)	0.03275 (19)	0.0553 (2)	−0.00550 (15)	0.01586 (18)	0.00201 (15)
F1	0.089 (3)	0.098 (3)	0.055 (2)	0.031 (2)	0.032 (2)	0.0041 (17)
F2	0.0630 (17)	0.098 (4)	0.072 (3)	0.0147 (17)	−0.0148 (16)	0.020 (2)
F3	0.112 (4)	0.062 (2)	0.0513 (16)	−0.017 (3)	0.005 (3)	0.0106 (15)
F1A	0.084 (4)	0.102 (6)	0.061 (5)	0.024 (4)	0.041 (3)	0.013 (4)
F2A	0.098 (7)	0.070 (4)	0.034 (3)	0.003 (5)	−0.020 (4)	−0.012 (2)
F3A	0.081 (5)	0.045 (2)	0.045 (3)	0.007 (3)	−0.004 (4)	−0.0009 (19)
F1B	0.092 (5)	0.079 (7)	0.040 (5)	−0.015 (5)	0.015 (4)	0.007 (4)
F2B	0.090 (7)	0.093 (6)	0.040 (4)	−0.004 (6)	0.009 (6)	−0.006 (4)
F3B	0.095 (7)	0.088 (7)	0.083 (7)	0.036 (6)	−0.005 (6)	0.020 (5)
O1	0.0366 (5)	0.0292 (5)	0.0457 (6)	−0.0035 (4)	0.0102 (4)	−0.0017 (4)
N1	0.0462 (8)	0.0456 (7)	0.0770 (10)	−0.0004 (6)	0.0265 (7)	0.0158 (7)
C1	0.0277 (6)	0.0294 (6)	0.0373 (7)	−0.0005 (5)	0.0057 (5)	0.0019 (5)
C2	0.0257 (6)	0.0314 (6)	0.0391 (7)	0.0030 (5)	0.0071 (5)	−0.0029 (5)
C3	0.0318 (6)	0.0339 (6)	0.0383 (7)	0.0031 (5)	0.0077 (5)	−0.0024 (5)
C4	0.0403 (7)	0.0446 (8)	0.0378 (7)	0.0080 (6)	0.0063 (6)	−0.0045 (6)
C5	0.0520 (9)	0.0505 (9)	0.0451 (9)	−0.0004 (7)	0.0027 (7)	−0.0155 (7)
C6	0.0462 (8)	0.0374 (7)	0.0575 (10)	−0.0054 (6)	0.0083 (7)	−0.0130 (7)
C7	0.0323 (6)	0.0316 (6)	0.0458 (8)	0.0015 (5)	0.0097 (6)	−0.0028 (5)
C8	0.0369 (7)	0.0427 (8)	0.0428 (8)	−0.0026 (6)	0.0093 (6)	0.0024 (6)
C9	0.0581 (10)	0.0584 (10)	0.0568 (10)	−0.0140 (8)	0.0227 (8)	0.0040 (8)
C10	0.0771 (13)	0.0818 (14)	0.0547 (11)	−0.0166 (11)	0.0343 (10)	−0.0042 (10)
C11	0.0743 (13)	0.0736 (13)	0.0495 (10)	−0.0156 (10)	0.0252 (9)	−0.0170 (9)
C12	0.0485 (9)	0.0528 (9)	0.0429 (8)	−0.0109 (7)	0.0111 (7)	−0.0079 (7)
C13	0.0311 (6)	0.0413 (7)	0.0357 (7)	−0.0030 (5)	0.0045 (5)	0.0006 (5)
C14	0.0584 (10)	0.0599 (10)	0.0412 (8)	0.0141 (8)	0.0076 (7)	−0.0022 (7)
C15	0.0296 (6)	0.0377 (7)	0.0538 (9)	0.0010 (5)	0.0028 (6)	0.0079 (6)
C16	0.0329 (7)	0.0379 (8)	0.0779 (12)	0.0043 (6)	0.0158 (7)	0.0000 (7)
C17	0.0317 (7)	0.0475 (9)	0.0802 (12)	0.0003 (6)	0.0158 (8)	0.0068 (8)
C18	0.072 (4)	0.133 (6)	0.089 (3)	0.010 (4)	0.037 (3)	0.057 (3)
C19	0.111 (6)	0.055 (3)	0.147 (6)	−0.028 (4)	0.055 (4)	0.011 (3)
C18A	0.077 (9)	0.056 (6)	0.063 (6)	−0.027 (6)	0.001 (6)	0.000 (5)
C19A	0.039 (5)	0.042 (6)	0.072 (7)	−0.007 (4)	0.014 (4)	−0.007 (5)

Geometric parameters (Å, º) top

S1—C7	1.7535 (15)	C6—H6A	0.9500
S1—C8	1.7602 (16)	C8—C9	1.392 (2)
F1—C14	1.354 (3)	C8—C13	1.397 (2)
F2—C14	1.370 (5)	C9—C10	1.374 (3)
F3—C14	1.280 (5)	C9—H9A	0.9500
F1A—C14	1.360 (7)	C10—C11	1.381 (3)
F1A—F3A	2.102 (9)	C10—H10A	0.9500
F2A—C14	1.273 (8)	C11—C12	1.385 (2)
F3A—C14	1.357 (9)	C11—H11A	0.9500
F1B—C14	1.443 (10)	C12—C13	1.386 (2)
F2B—C14	1.237 (9)	C12—H12A	0.9500
F3B—C14	1.292 (10)	C15—C16	1.529 (2)
O1—C1	1.4134 (15)	C15—H15A	0.9900
O1—H1A	0.87 (2)	C15—H15B	0.9900
N1—C18A	1.429 (14)	C16—C17	1.520 (2)
N1—C19	1.439 (8)	C16—H16A	0.9900
N1—C17	1.456 (2)	C16—H16B	0.9900
N1—C18	1.481 (7)	C17—H17A	0.9900
N1—C19A	1.517 (12)	C17—H17B	0.9900
C1—C13	1.5213 (19)	C18—H18A	0.9800
C1—C2	1.5263 (19)	C18—H18B	0.9800
C1—C15	1.5489 (19)	C18—H18C	0.9800
C2—C3	1.3873 (19)	C19—H19A	0.9800
C2—C7	1.3989 (19)	C19—H19B	0.9800
C3—C4	1.386 (2)	C19—H19C	0.9800
C3—H3A	0.9500	C18A—H18D	0.9800
C4—C5	1.388 (2)	C18A—H18E	0.9800
C4—C14	1.486 (2)	C18A—H18F	0.9800
C5—C6	1.374 (2)	C19A—H19D	0.9800
C5—H5A	0.9500	C19A—H19E	0.9800
C6—C7	1.394 (2)	C19A—H19F	0.9800

C7—S1—C8	99.63 (7)	F3—C14—F1A	77.7 (5)
C1—O1—H1A	109.8 (15)	F3B—C14—F1A	122.8 (9)
C18A—N1—C19	101.1 (8)	F2B—C14—F2	64.3 (9)
C18A—N1—C17	118.6 (10)	F3A—C14—F2	87.4 (5)
C19—N1—C17	112.2 (6)	F3—C14—F2	106.0 (4)
C19—N1—C18	111.1 (5)	F1—C14—F2	101.1 (3)
C17—N1—C18	108.1 (6)	F3B—C14—F2	59.2 (9)
C18A—N1—C19A	107.5 (9)	F1A—C14—F2	130.2 (5)
C17—N1—C19A	103.5 (8)	F2B—C14—F1B	101.8 (7)
C18—N1—C19A	116.8 (9)	F3A—C14—F1B	73.0 (7)
O1—C1—C13	108.24 (11)	F2A—C14—F1B	131.2 (7)
O1—C1—C2	110.70 (11)	F3—C14—F1B	48.9 (7)
C13—C1—C2	108.84 (10)	F1—C14—F1B	68.4 (7)
O1—C1—C15	111.19 (11)	F3B—C14—F1B	99.1 (8)
C13—C1—C15	107.85 (11)	F2—C14—F1B	138.9 (6)
C2—C1—C15	109.92 (11)	F2B—C14—C4	116.4 (6)
C3—C2—C7	118.09 (13)	F3A—C14—C4	111.1 (6)
C3—C2—C1	120.40 (12)	F2A—C14—C4	115.3 (6)
C7—C2—C1	121.50 (12)	F3—C14—C4	116.1 (3)
C4—C3—C2	120.78 (13)	F1—C14—C4	111.4 (2)
C4—C3—H3A	119.6	F3B—C14—C4	113.8 (7)
C2—C3—H3A	119.6	F1A—C14—C4	110.6 (3)
C3—C4—C5	120.41 (15)	F2—C14—C4	111.3 (3)
C3—C4—C14	119.30 (15)	F1B—C14—C4	109.4 (4)
C5—C4—C14	120.27 (15)	C16—C15—C1	117.70 (13)
C6—C5—C4	119.75 (15)	C16—C15—H15A	107.9
C6—C5—H5A	120.1	C1—C15—H15A	107.9
C4—C5—H5A	120.1	C16—C15—H15B	107.9
C5—C6—C7	119.83 (15)	C1—C15—H15B	107.9
C5—C6—H6A	120.1	H15A—C15—H15B	107.2
C7—C6—H6A	120.1	C17—C16—C15	115.14 (14)
C6—C7—C2	121.02 (14)	C17—C16—H16A	108.5
C6—C7—S1	117.41 (11)	C15—C16—H16A	108.5
C2—C7—S1	121.55 (11)	C17—C16—H16B	108.5
C9—C8—C13	120.68 (15)	C15—C16—H16B	108.5
C9—C8—S1	116.99 (12)	H16A—C16—H16B	107.5
C13—C8—S1	122.30 (11)	N1—C17—C16	113.97 (13)
C10—C9—C8	119.86 (17)	N1—C17—H17A	108.8
C10—C9—H9A	120.1	C16—C17—H17A	108.8
C8—C9—H9A	120.1	N1—C17—H17B	108.8
C9—C10—C11	120.25 (17)	C16—C17—H17B	108.8
C9—C10—H10A	119.9	H17A—C17—H17B	107.7
C11—C10—H10A	119.9	N1—C18—H18A	109.5
C10—C11—C12	119.87 (17)	N1—C18—H18B	109.5
C10—C11—H11A	120.1	H18A—C18—H18B	109.5
C12—C11—H11A	120.1	N1—C18—H18C	109.5
C13—C12—C11	121.09 (16)	H18A—C18—H18C	109.5
C13—C12—H12A	119.5	H18B—C18—H18C	109.5
C11—C12—H12A	119.5	N1—C19—H19A	109.5
C12—C13—C8	118.20 (14)	N1—C19—H19B	109.5
C12—C13—C1	121.02 (13)	H19A—C19—H19B	109.5
C8—C13—C1	120.74 (13)	N1—C19—H19C	109.5
F2B—C14—F3A	130.8 (9)	H19A—C19—H19C	109.5
F3A—C14—F2A	106.6 (6)	H19B—C19—H19C	109.5
F2B—C14—F3	126.1 (7)	N1—C18A—H18D	109.5
F2A—C14—F3	119.6 (6)	N1—C18A—H18E	109.5
F3A—C14—F1	129.6 (6)	H18D—C18A—H18E	109.5
F2A—C14—F1	77.8 (5)	N1—C18A—H18F	109.5
F3—C14—F1	109.7 (3)	H18D—C18A—H18F	109.5
F2B—C14—F3B	113.9 (9)	H18E—C18A—H18F	109.5
F2A—C14—F3B	80.3 (9)	N1—C19A—H19D	109.5
F3—C14—F3B	51.2 (9)	N1—C19A—H19E	109.5
F1—C14—F3B	134.7 (7)	H19D—C19A—H19E	109.5
F2B—C14—F1A	73.7 (9)	N1—C19A—H19F	109.5
F3A—C14—F1A	101.4 (6)	H19D—C19A—H19F	109.5
F2A—C14—F1A	110.8 (6)	H19E—C19A—H19F	109.5

O1—C1—C2—C3	−16.56 (16)	F1A—F3A—C14—F3	−10 (2)
C13—C1—C2—C3	−135.40 (12)	F1A—F3A—C14—F1	28.2 (6)
C15—C1—C2—C3	106.68 (14)	F1A—F3A—C14—F3B	141.1 (17)
O1—C1—C2—C7	164.96 (11)	F1A—F3A—C14—F2	130.6 (5)
C13—C1—C2—C7	46.11 (16)	F1A—F3A—C14—F1B	−12.8 (7)
C15—C1—C2—C7	−71.81 (15)	F1A—F3A—C14—C4	−117.6 (5)
C7—C2—C3—C4	3.40 (19)	F3A—F1A—C14—F2B	−129.4 (9)
C1—C2—C3—C4	−175.14 (12)	F3A—F1A—C14—F2A	−112.9 (7)
C2—C3—C4—C5	−0.8 (2)	F3A—F1A—C14—F3	4.3 (8)
C2—C3—C4—C14	177.44 (13)	F3A—F1A—C14—F1	−143.5 (7)
C3—C4—C5—C6	−2.0 (2)	F3A—F1A—C14—F3B	−21.1 (10)
C14—C4—C5—C6	179.71 (15)	F3A—F1A—C14—F2	−96.4 (8)
C4—C5—C6—C7	2.2 (2)	F3A—F1A—C14—F1B	24.2 (13)
C5—C6—C7—C2	0.4 (2)	F3A—F1A—C14—C4	117.9 (6)
C5—C6—C7—S1	−177.87 (13)	C3—C4—C14—F2B	−153.9 (11)
C3—C2—C7—C6	−3.2 (2)	C5—C4—C14—F2B	24.4 (11)
C1—C2—C7—C6	175.29 (13)	C3—C4—C14—F3A	39.4 (6)
C3—C2—C7—S1	175.02 (10)	C5—C4—C14—F3A	−142.3 (6)
C1—C2—C7—S1	−6.46 (17)	C3—C4—C14—F2A	160.8 (7)
C8—S1—C7—C6	149.19 (12)	C5—C4—C14—F2A	−20.9 (7)
C8—S1—C7—C2	−29.12 (12)	C3—C4—C14—F3	13.7 (5)
C7—S1—C8—C9	−148.84 (14)	C5—C4—C14—F3	−168.1 (4)
C7—S1—C8—C13	29.48 (14)	C3—C4—C14—F1	−112.9 (4)
C13—C8—C9—C10	−0.8 (3)	C5—C4—C14—F1	65.4 (4)
S1—C8—C9—C10	177.53 (17)	C3—C4—C14—F3B	70.5 (11)
C8—C9—C10—C11	−0.9 (3)	C5—C4—C14—F3B	−111.2 (11)
C9—C10—C11—C12	0.9 (4)	C3—C4—C14—F1A	−72.4 (8)
C10—C11—C12—C13	0.7 (3)	C5—C4—C14—F1A	105.9 (8)
C11—C12—C13—C8	−2.3 (3)	C3—C4—C14—F2	135.1 (4)
C11—C12—C13—C1	175.65 (16)	C5—C4—C14—F2	−46.7 (4)
C9—C8—C13—C12	2.4 (2)	C3—C4—C14—F1B	−39.2 (8)
S1—C8—C13—C12	−175.88 (12)	C5—C4—C14—F1B	139.0 (8)
C9—C8—C13—C1	−175.60 (15)	O1—C1—C15—C16	64.51 (17)
S1—C8—C13—C1	6.1 (2)	C13—C1—C15—C16	−176.96 (12)
O1—C1—C13—C12	16.06 (18)	C2—C1—C15—C16	−58.43 (16)
C2—C1—C13—C12	136.43 (14)	C1—C15—C16—C17	−86.15 (18)
C15—C1—C13—C12	−104.34 (16)	C18A—N1—C17—C16	84.4 (9)
O1—C1—C13—C8	−166.03 (13)	C19—N1—C17—C16	−158.3 (5)
C2—C1—C13—C8	−45.65 (17)	C18—N1—C17—C16	78.8 (4)
C15—C1—C13—C8	73.57 (16)	C19A—N1—C17—C16	−156.7 (7)
F1A—F3A—C14—F2B	78.2 (12)	C15—C16—C17—N1	71.3 (2)
F1A—F3A—C14—F2A	116.0 (6)

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of the C2–C7 and C8–C13 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.87 (2)	1.84 (2)	2.7141 (17)	176 (2)
C15—H15A···S1	0.99	2.76	3.4165 (15)	124
C5—H5A···Cg3ⁱ	0.95	2.96	3.798 (3)	148
C17—H17A···Cg2ⁱⁱ	0.99	2.97	3.949 (3)	170
C17—H17B···Cg3ⁱⁱ	0.99	2.83	3.659 (3)	142

Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₀F₃NOS
M_r	367.42
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	170
a, b, c (Å)	7.6183 (3), 13.9605 (4), 17.4172 (7)
β (°)	101.053 (4)
V (Å³)	1818.05 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.35 × 0.33 × 0.30

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2010)
T_min, T_max	0.929, 0.939
No. of measured, independent and observed [I > 2σ(I)] reflections	17330, 4697, 3901
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.676

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.116, 1.05
No. of reflections	4697
No. of parameters	306
No. of restraints	238
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.29

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), CrysAlis RED (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of the C2–C7 and C8–C13 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.87 (2)	1.84 (2)	2.7141 (17)	176 (2)
C15—H15A···S1	0.99	2.76	3.4165 (15)	123.8
C5—H5A···Cg3ⁱ	0.95	2.96	3.798 (3)	148
C17—H17A···Cg2ⁱⁱ	0.99	2.97	3.949 (3)	170
C17—H17B···Cg3ⁱⁱ	0.99	2.83	3.659 (3)	142

Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) x−1, y, z.

Acknowledgements

MSS thanks the University of Mysore and R. L. Fine Chem, Bangalore, for access to their research facilities. JPJ acknowledges the NSF–MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.

References

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Post, M. L., Kennard, O. & Horn, A. S. (1975a). Acta Cryst. B31, 2724–2726. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
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