1-(2-Hy­droxy­eth­yl)-4-[3-(2-trifluoro­methyl-9H-thioxanthen-9-yl­idene)prop­yl]piperazine-1,4-diium dichloride: the dihydro­chloride salt of flupentixol

Siddegowda, M.S.; Butcher, R.J.; Akkurt, M.; Yathirajan, H.S.; Narayana, B.

doi:10.1107/S1600536811028182

1-(2-Hydroxyethyl)-4-[3-(2-trifluoromethyl-9H-thioxanthen-9-ylidene)propyl]piperazine-1,4-diium dichloride: the dihydrochloride salt of flupentixol

M. S. Siddegowda, R. J. Butcher, M. Akkurt, H. S. Yathirajan and B. Narayana

In the title compound, C₂₃H₂₇F₃N₂OS⁺·2Cl⁻, the piperazinediium ring adopts a chair conformation. The dihedral angle between the two outer aromatic rings of the 9H-thioxanthene unit is 40.35 (18)°. The F atoms in the trifluoromethyl group are disordered over two sets of sites with occupancies of 0.803 (6) and 0.197 (6). In the crystal, molecules are connected by N—H

Cl, O—H

Cl C—H

O and C—H

Cl hydrogen bonds, forming chains propagating along [001]. There are also C—H

π interactions present in the crystal structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536811028182/su2290sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536811028182/su2290Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S1600536811028182/su2290Isup3.cml Supplementary material

CCDC reference: 841254

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.005 Å
Disorder in main residue
R factor = 0.069
wR factor = 0.230
Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.36
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for          S
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C14
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0050 Ang
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          3
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          6
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600        124

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          7
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained Atom Sites ....          6
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT Unusually Large.       0.13
PLAT301_ALERT_3_G Note: Main Residue  Disorder ...................         10 Perc.
PLAT432_ALERT_2_G Short Inter X...Y Contact  C6     ..  F3A     ..       2.95 Ang.
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         48

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   7 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   7 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

Flupentixol (formally called flupenthixol), 2-(4-(3-(2-(trifluoromethyl)-9H-thioxanthen-9-yl)propyl) piperazin-1-yl)ethanol, is a typical antipsychotic drug of the thioxanthene class. In addition to single drug preparations, it is also available as a deanxit; a combination product containing both melitracen and flupentixol. The antidepressant action of flupentixol has been described by (Robertson & Trimble, 1981). The crystal structures of α-flupenthixol (Post et al., 1975a) and β-flupenthixol (Post et al., 1975b) have been reported. In view of the importance of flupentixol, herein we report on the crystal structure of its Dihydrochloride salt.

In the molecule of the title compound, (Fig. 1), the piperazinediium ring exhibits a chair conformation, with puckering parameters Q_T = 0.584 (4) Å, θ = 5.5 (3) ° and ϕ = 175 (4) ° (Cremer & Pople, 1975). The two aromatic rings of the 9H-thioxanthene unit make a dihedral angle of 40.35 (18)°.

The crystal structure of the title compound is stabilized by N—H···Cl, O—H···Cl, C—H···O and C—H···Cl hydrogen bonds, forming chains propagating along the c axis direction (Table 1, Fig. 2). There are also C—H···π interactions present (Table 1).

Related literature top

For the antidepressant action of flupentixol, see: Robertson & Trimble (1981). For related structures, see: Post et al. (1975a,b). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

The title compound was a gift sample from R. L. Fine Chemicals, Bangalore, India. X-ray quality crystals were obtained from a 1:1 mixture of ethanol and methanol by slow evaporation (m.p.: 510–512 K).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (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: PLATON (Spek, 2009).

Figures top

	Fig. 1. ORTEP view of the title molecule, showing the atom labeling scheme and the displacement ellipsoids drawn at the 30% probability level. Only the major components of the disordered CF₃ group are shown.
	Fig. 2. Crystal packing diagram, with the hydrogen bonding (dashed lines), of the title compound viewed along the b axis. Only the major components of the disordered CF₃ group are shown.

1-(2-Hydroxyethyl)-4-[3-(2-trifluoromethyl-9H-thioxanthen-9- ylidene)propyl]piperazine-1,4-diium dichloride top

Crystal data top

C₂₃H₂₇F₃N₂OS²⁺·2Cl⁻	F(000) = 2112
M_r = 507.44	D_x = 1.346 Mg m⁻³
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -C 2yc	Cell parameters from 3191 reflections
a = 34.1750 (17) Å	θ = 5.2–75.3°
b = 7.1613 (3) Å	µ = 3.46 mm⁻¹
c = 22.6351 (11) Å	T = 295 K
β = 115.307 (6)°	Prism, colourless
V = 5008.0 (5) Å³	0.43 × 0.34 × 0.21 mm
Z = 8

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	5032 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3792 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
Detector resolution: 10.5081 pixels mm^-1	θ_max = 75.4°, θ_min = 5.5°
ω scans	h = −42→41
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	k = −8→8
T_min = 0.430, T_max = 1.000	l = −28→17
9840 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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.230	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.1341P)² + 2.8648P] where P = (F_o² + 2F_c²)/3
5032 reflections	(Δ/σ)_max < 0.001
289 parameters	Δρ_max = 1.02 e Å⁻³
48 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

C₂₃H₂₇F₃N₂OS²⁺·2Cl⁻	V = 5008.0 (5) Å³
M_r = 507.44	Z = 8
Monoclinic, C2/c	Cu Kα radiation
a = 34.1750 (17) Å	µ = 3.46 mm⁻¹
b = 7.1613 (3) Å	T = 295 K
c = 22.6351 (11) Å	0.43 × 0.34 × 0.21 mm
β = 115.307 (6)°

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	5032 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	3792 reflections with I > 2σ(I)
T_min = 0.430, T_max = 1.000	R_int = 0.028
9840 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.069	48 restraints
wR(F²) = 0.230	H-atom parameters constrained
S = 1.05	Δρ_max = 1.02 e Å⁻³
5032 reflections	Δρ_min = −0.43 e Å⁻³
289 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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)
S	0.57461 (4)	1.14222 (16)	0.35221 (7)	0.0884 (4)
F1B	0.57123 (16)	0.4027 (6)	0.17114 (19)	0.1148 (16)	0.803 (6)
F2B	0.5404 (2)	0.6060 (7)	0.0960 (2)	0.153 (2)	0.803 (6)
F3B	0.50494 (14)	0.4598 (8)	0.1387 (3)	0.156 (2)	0.803 (6)
O1	0.81039 (14)	0.4005 (6)	0.22005 (15)	0.1096 (15)
N1	0.74387 (7)	0.4815 (4)	0.39823 (12)	0.0526 (7)
N2	0.81206 (8)	0.4717 (4)	0.35317 (11)	0.0554 (8)
C1	0.60586 (9)	0.7385 (5)	0.38628 (16)	0.0576 (9)
C2	0.58158 (6)	0.7828 (3)	0.31479 (8)	0.0575 (9)
C3	0.57390 (7)	0.6452 (2)	0.26781 (10)	0.0638 (10)
C4	0.55139 (7)	0.6884 (3)	0.20190 (9)	0.0691 (11)
C5	0.53658 (8)	0.8693 (4)	0.18297 (8)	0.0803 (14)
C6	0.54426 (8)	1.0069 (3)	0.22994 (12)	0.0813 (16)
C7	0.56677 (7)	0.9636 (3)	0.29585 (11)	0.0675 (11)
C8	0.57315 (10)	1.0114 (6)	0.41747 (19)	0.0704 (11)
C9	0.55696 (12)	1.0993 (8)	0.4577 (2)	0.0892 (18)
C10	0.55546 (13)	1.0009 (10)	0.5087 (2)	0.098 (2)
C11	0.56923 (16)	0.8215 (10)	0.5202 (2)	0.098 (2)
C12	0.58549 (13)	0.7320 (7)	0.48050 (19)	0.0804 (14)
C13	0.58772 (10)	0.8272 (6)	0.42855 (17)	0.0639 (10)
C14	0.54294 (13)	0.5409 (7)	0.15137 (18)	0.0959 (18)
C15	0.64145 (11)	0.6333 (5)	0.41210 (17)	0.0631 (10)
C16	0.66663 (10)	0.5476 (5)	0.37845 (17)	0.0623 (10)
C17	0.71416 (10)	0.5881 (5)	0.41901 (15)	0.0574 (9)
C18	0.78999 (10)	0.5299 (6)	0.44121 (14)	0.0654 (12)
C19	0.82119 (10)	0.4273 (6)	0.42243 (15)	0.0669 (12)
C20	0.76719 (10)	0.4095 (5)	0.31076 (15)	0.0609 (10)
C21	0.73502 (9)	0.5109 (5)	0.32828 (14)	0.0585 (9)
C22	0.84554 (11)	0.3868 (6)	0.33492 (18)	0.0703 (13)
C23	0.84521 (12)	0.4698 (7)	0.27293 (19)	0.0754 (14)
F3A	0.5493 (6)	0.3669 (14)	0.1704 (10)	0.156 (2)	0.197 (6)
F1A	0.5709 (4)	0.581 (2)	0.1264 (8)	0.1148 (16)	0.197 (6)
F2A	0.5040 (3)	0.556 (3)	0.1030 (6)	0.153 (2)	0.197 (6)
Cl1	0.78205 (5)	0.58962 (13)	0.08841 (5)	0.0878 (4)
Cl2	0.81966 (4)	0.89329 (16)	0.34901 (7)	0.0992 (4)
H1B	0.80170	0.47920	0.19100	0.1640*
H5A	0.52150	0.89820	0.13890	0.0960*
H2A	0.81320	0.59790	0.34950	0.0670*
H3A	0.58380	0.52420	0.28050	0.0770*
H1A	0.74020	0.35790	0.40370	0.0630*
H11A	0.56790	0.75720	0.55500	0.1180*
H12A	0.59480	0.60870	0.48890	0.0960*
H15A	0.65200	0.61010	0.45670	0.0760*
H16A	0.65730	0.60030	0.33510	0.0750*
H6A	0.53430	1.12790	0.21730	0.0980*
H9A	0.54740	1.22240	0.45000	0.1070*
H10A	0.54480	1.05820	0.53570	0.1170*
H18A	0.79620	0.50020	0.48620	0.0790*
H18B	0.79410	0.66320	0.43860	0.0790*
H19A	0.85060	0.46350	0.45110	0.0800*
H19B	0.81840	0.29390	0.42710	0.0800*
H20A	0.76480	0.27620	0.31590	0.0730*
H20B	0.76080	0.43360	0.26540	0.0730*
H21A	0.73620	0.64340	0.32030	0.0700*
H21B	0.70610	0.46690	0.30050	0.0700*
H22A	0.84050	0.25350	0.32890	0.0840*
H22B	0.87390	0.40520	0.37060	0.0840*
H23A	0.84330	0.60480	0.27400	0.0900*
H23B	0.87180	0.43780	0.26970	0.0900*
H16B	0.66180	0.41380	0.37420	0.0750*
H17A	0.71910	0.72070	0.41650	0.0690*
H17B	0.72140	0.55860	0.46430	0.0690*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S	0.0929 (7)	0.0654 (6)	0.1139 (8)	0.0122 (5)	0.0508 (6)	0.0065 (5)
F1B	0.132 (3)	0.112 (3)	0.093 (2)	0.009 (2)	0.041 (2)	−0.020 (2)
F2B	0.246 (6)	0.139 (3)	0.070 (2)	−0.015 (4)	0.064 (3)	0.007 (2)
F3B	0.129 (3)	0.150 (4)	0.156 (4)	−0.058 (3)	0.030 (3)	−0.033 (3)
O1	0.124 (3)	0.129 (3)	0.0652 (16)	−0.048 (2)	0.0302 (17)	−0.0017 (17)
N1	0.0480 (12)	0.0530 (13)	0.0522 (13)	0.0016 (10)	0.0169 (10)	0.0101 (10)
N2	0.0478 (12)	0.0677 (15)	0.0464 (12)	−0.0014 (11)	0.0159 (9)	0.0046 (11)
C1	0.0474 (14)	0.0607 (17)	0.0644 (16)	−0.0007 (13)	0.0237 (12)	0.0043 (14)
C2	0.0438 (13)	0.0623 (17)	0.0693 (18)	0.0024 (12)	0.0269 (12)	0.0100 (15)
C3	0.0514 (15)	0.0686 (19)	0.0668 (18)	−0.0023 (14)	0.0208 (13)	0.0109 (16)
C4	0.0506 (16)	0.085 (2)	0.0688 (19)	−0.0043 (16)	0.0227 (14)	0.0097 (18)
C5	0.0608 (19)	0.106 (3)	0.075 (2)	0.014 (2)	0.0298 (17)	0.032 (2)
C6	0.077 (2)	0.085 (3)	0.094 (3)	0.027 (2)	0.048 (2)	0.037 (2)
C7	0.0565 (17)	0.072 (2)	0.083 (2)	0.0091 (15)	0.0385 (16)	0.0152 (18)
C8	0.0448 (14)	0.084 (2)	0.079 (2)	0.0041 (15)	0.0231 (14)	−0.0116 (19)
C9	0.0517 (18)	0.114 (4)	0.091 (3)	0.011 (2)	0.0202 (17)	−0.025 (3)
C10	0.0555 (19)	0.153 (5)	0.083 (3)	0.001 (3)	0.0279 (18)	−0.033 (3)
C11	0.078 (3)	0.149 (5)	0.073 (2)	−0.024 (3)	0.037 (2)	−0.011 (3)
C12	0.072 (2)	0.102 (3)	0.068 (2)	−0.010 (2)	0.0307 (17)	−0.002 (2)
C13	0.0429 (13)	0.081 (2)	0.0644 (18)	−0.0036 (14)	0.0198 (12)	−0.0025 (16)
C14	0.096 (3)	0.108 (4)	0.067 (2)	−0.014 (3)	0.019 (2)	−0.004 (2)
C15	0.0567 (16)	0.0662 (19)	0.0625 (17)	0.0038 (14)	0.0217 (14)	0.0051 (15)
C16	0.0529 (16)	0.0620 (18)	0.0651 (18)	0.0104 (14)	0.0185 (13)	0.0022 (15)
C17	0.0579 (16)	0.0559 (17)	0.0552 (15)	0.0031 (13)	0.0212 (13)	0.0033 (13)
C18	0.0523 (15)	0.095 (3)	0.0416 (14)	−0.0110 (16)	0.0130 (11)	0.0023 (15)
C19	0.0426 (14)	0.102 (3)	0.0483 (15)	−0.0018 (15)	0.0119 (11)	0.0122 (16)
C20	0.0485 (15)	0.075 (2)	0.0498 (15)	0.0028 (14)	0.0119 (12)	−0.0014 (14)
C21	0.0493 (14)	0.0712 (19)	0.0456 (14)	0.0073 (14)	0.0112 (11)	0.0058 (13)
C22	0.0511 (16)	0.091 (3)	0.0645 (18)	0.0055 (16)	0.0207 (14)	−0.0011 (17)
C23	0.0643 (19)	0.097 (3)	0.072 (2)	−0.0101 (19)	0.0360 (16)	−0.010 (2)
F3A	0.129 (3)	0.150 (4)	0.156 (4)	−0.058 (3)	0.030 (3)	−0.033 (3)
F1A	0.132 (3)	0.112 (3)	0.093 (2)	0.009 (2)	0.041 (2)	−0.020 (2)
F2A	0.246 (6)	0.139 (3)	0.070 (2)	−0.015 (4)	0.064 (3)	0.007 (2)
Cl1	0.1424 (10)	0.0536 (5)	0.0658 (5)	0.0110 (5)	0.0430 (6)	−0.0025 (4)
Cl2	0.0772 (6)	0.0709 (6)	0.1183 (9)	−0.0076 (5)	0.0121 (6)	0.0168 (6)

Geometric parameters (Å, º) top

S—C7	1.745 (3)	C11—C12	1.398 (7)
S—C8	1.768 (4)	C12—C13	1.389 (6)
F1A—C14	1.333 (16)	C15—C16	1.503 (5)
F1B—C14	1.321 (7)	C16—C17	1.513 (5)
F2A—C14	1.318 (13)	C18—C19	1.498 (5)
F2B—C14	1.305 (6)	C20—C21	1.505 (5)
F3A—C14	1.306 (12)	C22—C23	1.520 (6)
F3B—C14	1.337 (7)	C3—H3A	0.9300
O1—C23	1.370 (6)	C5—H5A	0.9300
O1—H1B	0.8200	C6—H6A	0.9300
N1—C18	1.497 (4)	C9—H9A	0.9300
N1—C21	1.494 (4)	C10—H10A	0.9300
N1—C17	1.498 (5)	C11—H11A	0.9300
N2—C19	1.496 (4)	C12—H12A	0.9300
N2—C20	1.488 (4)	C15—H15A	0.9300
N2—C22	1.501 (5)	C16—H16A	0.9700
N1—H1A	0.9100	C16—H16B	0.9700
N2—H2A	0.9100	C17—H17A	0.9700
C1—C13	1.487 (5)	C17—H17B	0.9700
C1—C2	1.503 (4)	C18—H18A	0.9700
C1—C15	1.335 (5)	C18—H18B	0.9700
C2—C7	1.390 (3)	C19—H19A	0.9700
C2—C3	1.390 (3)	C19—H19B	0.9700
C3—C4	1.390 (3)	C20—H20A	0.9700
C4—C14	1.492 (5)	C20—H20B	0.9700
C4—C5	1.390 (4)	C21—H21A	0.9700
C5—C6	1.390 (3)	C21—H21B	0.9700
C6—C7	1.390 (3)	C22—H22A	0.9700
C8—C13	1.394 (6)	C22—H22B	0.9700
C8—C9	1.401 (6)	C23—H23A	0.9700
C9—C10	1.372 (7)	C23—H23B	0.9700
C10—C11	1.355 (10)

C7—S—C8	99.91 (17)	N2—C22—C23	113.0 (3)
C23—O1—H1B	109.00	O1—C23—C22	109.0 (4)
C17—N1—C21	113.8 (2)	C2—C3—H3A	120.00
C18—N1—C21	109.6 (2)	C4—C3—H3A	120.00
C17—N1—C18	110.2 (3)	C4—C5—H5A	120.00
C19—N2—C22	111.1 (3)	C6—C5—H5A	120.00
C20—N2—C22	113.4 (3)	C5—C6—H6A	120.00
C19—N2—C20	108.0 (3)	C7—C6—H6A	120.00
C17—N1—H1A	108.00	C8—C9—H9A	121.00
C18—N1—H1A	108.00	C10—C9—H9A	121.00
C21—N1—H1A	108.00	C9—C10—H10A	119.00
C19—N2—H2A	108.00	C11—C10—H10A	120.00
C20—N2—H2A	108.00	C10—C11—H11A	120.00
C22—N2—H2A	108.00	C12—C11—H11A	120.00
C13—C1—C15	120.8 (3)	C11—C12—H12A	120.00
C2—C1—C13	114.4 (3)	C13—C12—H12A	120.00
C2—C1—C15	124.8 (3)	C1—C15—H15A	116.00
C3—C2—C7	119.99 (17)	C16—C15—H15A	116.00
C1—C2—C3	120.7 (2)	C15—C16—H16A	110.00
C1—C2—C7	119.3 (2)	C15—C16—H16B	110.00
C2—C3—C4	120.01 (16)	C17—C16—H16A	110.00
C3—C4—C5	119.98 (17)	C17—C16—H16B	110.00
C3—C4—C14	120.2 (2)	H16A—C16—H16B	108.00
C5—C4—C14	119.9 (2)	N1—C17—H17A	109.00
C4—C5—C6	120.01 (17)	N1—C17—H17B	109.00
C5—C6—C7	120.0 (2)	C16—C17—H17A	109.00
S—C7—C2	122.40 (17)	C16—C17—H17B	109.00
S—C7—C6	117.57 (17)	H17A—C17—H17B	108.00
C2—C7—C6	120.0 (2)	N1—C18—H18A	109.00
S—C8—C13	121.1 (3)	N1—C18—H18B	109.00
C9—C8—C13	121.2 (4)	C19—C18—H18A	109.00
S—C8—C9	117.7 (3)	C19—C18—H18B	109.00
C8—C9—C10	118.9 (5)	H18A—C18—H18B	108.00
C9—C10—C11	120.9 (5)	N2—C19—H19A	110.00
C10—C11—C12	120.8 (5)	N2—C19—H19B	110.00
C11—C12—C13	120.0 (5)	C18—C19—H19A	110.00
C1—C13—C12	121.6 (4)	C18—C19—H19B	110.00
C1—C13—C8	120.2 (3)	H19A—C19—H19B	108.00
C8—C13—C12	118.2 (4)	N2—C20—H20A	110.00
F1B—C14—F2B	109.4 (5)	N2—C20—H20B	109.00
F1B—C14—F3B	104.5 (5)	C21—C20—H20A	110.00
F1B—C14—C4	113.4 (3)	C21—C20—H20B	110.00
F2B—C14—F3B	106.8 (5)	H20A—C20—H20B	108.00
F2B—C14—C4	113.3 (4)	N1—C21—H21A	109.00
F3B—C14—C4	108.9 (4)	N1—C21—H21B	109.00
F3A—C14—C4	118.2 (9)	C20—C21—H21A	109.00
F1A—C14—C4	103.5 (7)	C20—C21—H21B	109.00
F2A—C14—C4	112.0 (9)	H21A—C21—H21B	108.00
F2A—C14—F3A	108.6 (13)	N2—C22—H22A	109.00
F1A—C14—F2A	106.4 (9)	N2—C22—H22B	109.00
F1A—C14—F3A	107.3 (12)	C23—C22—H22A	109.00
C1—C15—C16	128.4 (3)	C23—C22—H22B	109.00
C15—C16—C17	108.2 (3)	H22A—C22—H22B	108.00
N1—C17—C16	114.1 (3)	O1—C23—H23A	110.00
N1—C18—C19	112.4 (3)	O1—C23—H23B	110.00
N2—C19—C18	109.8 (3)	C22—C23—H23A	110.00
N2—C20—C21	110.7 (3)	C22—C23—H23B	110.00
N1—C21—C20	111.8 (3)	H23A—C23—H23B	108.00

C8—S—C7—C2	−31.8 (3)	C3—C2—C7—C6	0.0 (4)
C8—S—C7—C6	147.3 (2)	C2—C3—C4—C5	0.0 (4)
C7—S—C8—C9	−148.7 (3)	C2—C3—C4—C14	−179.8 (3)
C7—S—C8—C13	31.5 (4)	C3—C4—C5—C6	0.0 (4)
C18—N1—C17—C16	−179.7 (3)	C14—C4—C5—C6	179.8 (3)
C21—N1—C17—C16	56.7 (4)	C3—C4—C14—F1B	−25.0 (5)
C17—N1—C18—C19	−179.9 (3)	C3—C4—C14—F2B	−150.5 (4)
C21—N1—C18—C19	−53.9 (4)	C3—C4—C14—F3B	90.8 (4)
C17—N1—C21—C20	176.9 (3)	C5—C4—C14—F1B	155.2 (4)
C18—N1—C21—C20	53.0 (4)	C5—C4—C14—F2B	29.8 (6)
C20—N2—C19—C18	−60.8 (4)	C5—C4—C14—F3B	−89.0 (4)
C22—N2—C19—C18	174.2 (3)	C4—C5—C6—C7	0.0 (4)
C19—N2—C20—C21	60.8 (4)	C5—C6—C7—S	−179.1 (2)
C22—N2—C20—C21	−175.6 (3)	C5—C6—C7—C2	0.0 (4)
C19—N2—C22—C23	−164.1 (3)	S—C8—C9—C10	180.0 (4)
C20—N2—C22—C23	74.0 (4)	C13—C8—C9—C10	−0.2 (6)
C13—C1—C2—C3	−138.9 (3)	S—C8—C13—C1	1.5 (5)
C13—C1—C2—C7	41.1 (4)	S—C8—C13—C12	−179.7 (3)
C15—C1—C2—C3	42.8 (5)	C9—C8—C13—C1	−178.4 (4)
C15—C1—C2—C7	−137.2 (3)	C9—C8—C13—C12	0.5 (6)
C2—C1—C13—C8	−41.3 (5)	C8—C9—C10—C11	−0.2 (7)
C2—C1—C13—C12	139.9 (4)	C9—C10—C11—C12	0.2 (8)
C15—C1—C13—C8	137.1 (4)	C10—C11—C12—C13	0.1 (7)
C15—C1—C13—C12	−41.7 (6)	C11—C12—C13—C1	178.4 (4)
C2—C1—C15—C16	4.3 (6)	C11—C12—C13—C8	−0.4 (6)
C13—C1—C15—C16	−173.9 (4)	C1—C15—C16—C17	132.6 (4)
C1—C2—C3—C4	180.0 (2)	C15—C16—C17—N1	169.2 (3)
C7—C2—C3—C4	0.0 (4)	N1—C18—C19—N2	58.8 (4)
C1—C2—C7—S	−0.9 (3)	N2—C20—C21—N1	−58.1 (4)
C1—C2—C7—C6	−180.0 (3)	N2—C22—C23—O1	−75.4 (5)
C3—C2—C7—S	179.1 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C2–C7 and C8–C13 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1ⁱ	0.91	2.10	2.997 (3)	168
O1—H1B···Cl1	0.82	2.27	3.030 (4)	155
N2—H2A···Cl2	0.91	2.13	3.035 (3)	175
C17—H17A···Cl1ⁱⁱ	0.97	2.64	3.600 (4)	169
C18—H18A···Cl1ⁱⁱⁱ	0.97	2.64	3.561 (3)	159
C20—H20B···O1	0.97	2.34	2.999 (6)	125
C21—H21A···O1ⁱⁱ	0.97	2.35	3.153 (6)	140
C22—H22A···Cl2^iv	0.97	2.77	3.690 (4)	160
C19—H19A···Cg2^v	0.97	2.65	3.618 (4)	176
C23—H23B···Cg1ⁱ	0.97	2.69	3.658 (5)	174

Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) −x+3/2, y+1/2, −z+1/2; (iii) x, −y+1, z+1/2; (iv) x, y−1, z; (v) −x+3/2, −y+3/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₃H₂₇F₃N₂OS²⁺·2Cl⁻
M_r	507.44
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	295
a, b, c (Å)	34.1750 (17), 7.1613 (3), 22.6351 (11)
β (°)	115.307 (6)
V (Å³)	5008.0 (5)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	3.46
Crystal size (mm)	0.43 × 0.34 × 0.21

Data collection
Diffractometer	Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)
T_min, T_max	0.430, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	9840, 5032, 3792
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.230, 1.05
No. of reflections	5032
No. of parameters	289
No. of restraints	48
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.02, −0.43

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009).