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In the title salt, C23H27F3N2OS+·2C4H3O4, a non-merohedral twin [ratio of the twin components = 0.402 (1):0.598 (1)], the –CF3 group is disordered over two sets of sites with occupancy factors in the ratio 0.873 (2):0.127 (2). The dihedral angle between the two outer aromatic rings of the 9H-thioxanthene unit, whose thio­pyran ring has a screw-boat conformation, is 33.01 (9)°. The diprotonated piperazine ring adopts a chair conformation. In the crystal, inter­molecular O—H...O, N—H...O and C—H...O hydrogen bonds between neighboring mol­ecules form zigzag chains along the a axis and contribute to the stabilization of the packing.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053681102722X/tk2763sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053681102722X/tk2763Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S160053681102722X/tk2763Isup3.cml
Supplementary material

CCDC reference: 841203

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.003 Å
  • Disorder in main residue
  • R factor = 0.055
  • wR factor = 0.162
  • Data-to-parameter ratio = 27.0

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT924_ALERT_1_A The Reported and Calculated Rho(min) Differ by . 5.46 eA-3
Author Response: Both cif and fcf files were generated during the last refinement. This was refined as a non-merohedral twin and thus an unmerged hkl file in hklf 5 format had to be used. This is the source of the discrepancies between what is contained in the cif and fcf files.
PLAT926_ALERT_1_A Reported and Calculated   R1 Differ by .........    -0.3132
Author Response: Both cif and fcf files were generated during the last refinement. This was refined as a non-merohedral twin and thus an unmerged hkl file in hklf 5 format had to be used. This is the source of the discrepancies between what is contained in the cif and fcf files.
PLAT927_ALERT_1_A Reported and Calculated  wR2 Differ by .........    -0.7292
Author Response: Both cif and fcf files were generated during the last refinement. This was refined as a non-merohedral twin and thus an unmerged hkl file in hklf 5 format had to be used. This is the source of the discrepancies betwee what is contained in the cif and fcf files.
PLAT928_ALERT_1_A Reported and Calculated    S value   Differ by .     -3.463
Author Response: Both cif and fcf files were generated during the last refinement. This was refined as a non-merohedral twin and thus an unmerged hkl file in hklf 5 format had to be used. This is the source of the discrepancies between what is contained in the cif and fcf files.

Alert level B PLAT021_ALERT_1_B Ratio Unique / Expected Reflections too High ... 1.805
Alert level C PLAT213_ALERT_2_C Atom F3A has ADP max/min Ratio ..... 3.1 prola PLAT213_ALERT_2_C Atom F3B has ADP max/min Ratio ..... 3.1 prola PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C8 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.9 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 3.0 PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 2 PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 103
Alert level G PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 7 PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF .... ? PLAT301_ALERT_3_G Note: Main Residue Disorder ................... 10 Perc. PLAT432_ALERT_2_G Short Inter X...Y Contact C6 .. F2B .. 2.93 Ang. PLAT432_ALERT_2_G Short Inter X...Y Contact C10 .. F3B .. 2.79 Ang. PLAT432_ALERT_2_G Short Inter X...Y Contact C12 .. F1B .. 2.91 Ang. PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 4 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 12
4 ALERT level A = Most likely a serious problem - resolve or explain 1 ALERT level B = A potentially serious problem, consider carefully 7 ALERT level C = Check. Ensure it is not caused by an omission or oversight 8 ALERT level G = General information/check it is not something unexpected 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 9 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Comment top

Flupentixol (systematic IUPAC name: 2-[4-[3-[(EZ)-2-(trifluoromethyl)-9H-thioxanthen-9-ylidene] propyl]piperazin-1-yl]ethanol is a typical antipsychotic drug of the thioxanthene class. In addition to pure drug preparations, it is also available as deanxit, a combination product containing both melitracen and flupentixol.The antidepressant action of flupentixol has been described (Robertson & Trimble, 1981). The crystal structures of α-flupenthixol (Post et al., 1975b), β-flupenthixol (Post et al., 1975a) and piflutixol (Jones et al., 1977) have been reported. In view of the importance of flupentixol, this paper reports the crystal structure of the title salt, (I), C23H27F3N2+OS2.2[C4H3O4-], formed by the reaction of flupentixol and fumaric acid.

The crystal studied was a non-merohedral twin, the ratio of the twin components being 0.402 (1): 0.598 (1). In (I), Fig. 1, the thiopyran ring of the 9H-thioxanthene ring system (S1/C1/C2/C7C9/C14) has a screw-boat conformation: the puckering parameters (Cremer & Pople, 1975) of QT = 0.5118 (15) Å, θ = 87.53 (19)° and ϕ = 3.2 (2) °. The dihedral angle between the two outer aromatic rings of the 9H-thioxanthene unit is 33.01 (9) °. The diprotonated piperazine ring (N1/N2/C18–C21) adopts a chair conformation with puckering parameters QT = 0.580 (13) Å, θ = 178.76 (12) ° and ϕ = 177 (7) °.

In the crystal structure, intermolecular O—H···O, N—H···O and C—H···O hydrogen bonds (Table 1) contributes to crystal packing forming the zigzag chains parallel to the [100] direction (Fig. 2).

Related literature top

The title compound was formed by the reaction of flupentixol (systematic name: 2-[4-[3-[(EZ)-2-(trifluoromethyl)-9H-thioxanthen-9-ylidene]propyl]piperazin-1-yl]ethanol and fumaric acid. For the antidepressant action of flupentixol, see: Robertson & Trimble, (1981). For related structures, see: Post et al. (1975a,b); Jones et al. (1977). For ring puckering parameters, see: Cremer & Pople (1975).

Experimental top

Flupenthixol base (2.0 g, 0.046 mol) was dissolved in 10 ml of ethyl acetate and fumaric acid (1.067 g, 0.092 mol) was added at 323 K. The solution was stirred in a round bottomed flask at 343 K for 30 min. The mixture was cooled to room temperature and the product formed was filtered and dried. X-ray quality crystals were obtained from a 1:1 mixture of dichloromethane and methanol by slow evaporation (M.pt.: 431-433 K).

Refinement top

All H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.93–0.97 Å, N–H = 0.91 Å and O–H = 0.82 Å, and with Uiso(H) = 1.5Ueq(O) for hydroxyl H atoms and 1.2Ueq(C) for other H atoms. The CF3 group is disordered over two sets of sites with occupations of 0.873 (2) and 0.127 (2), respectively. The structure was refined as a non-merohedral twin (using HKLF 5 in SHELXL) with the final ratio of the twin components being 0.402 (1):0.598 (1); as such there is no value for Rint.

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: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. Molecular structure of (I) with the atom labeling scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level. Hydrogen bond connections between the components of the asymmetric unit are shown as dashed lines. Only the major orientation of the disordered CF3 group is shown.
[Figure 2] Fig. 2. Perspective view of the crystal packing and hydrogen bonding (dashed lines) of (I) down the b axis.
1-(2-Hydroxyethyl)-4-{3-[(E)-2-(trifluoromethyl)-9H-thioxanthen- 9-ylidene]propyl}piperazine-1,4-diium bis(3-carboxyprop-2-enoate) top
Crystal data top
C23H27F3N2OS2+·2C4H3O4Z = 2
Mr = 666.66F(000) = 696
Triclinic, P1Dx = 1.422 Mg m3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54184 Å
a = 6.4175 (2) ÅCell parameters from 5369 reflections
b = 9.6185 (4) Åθ = 4.6–75.4°
c = 25.5771 (10) ŵ = 1.59 mm1
α = 96.377 (4)°T = 295 K
β = 96.295 (3)°Thick needle, colourless
γ = 92.774 (3)°0.53 × 0.17 × 0.12 mm
V = 1556.63 (10) Å3
Data collection top
Oxford Diffraction Xcalibur Ruby Gemini
diffractometer
11625 independent reflections
Radiation source: Enhance (Cu) X-ray Source9926 reflections with i > 2σ(i)
Graphite monochromatorRint = 0.000
Detector resolution: 10.5081 pixels mm-1θmax = 75.7°, θmin = 4.6°
ω scansh = 85
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2007)
k = 1112
Tmin = 0.643, Tmax = 1.000l = 3131
11625 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.162H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0915P)2 + 0.2879P]
where P = (Fo2 + 2Fc2)/3
11625 reflections(Δ/σ)max = 0.001
430 parametersΔρmax = 0.47 e Å3
12 restraintsΔρmin = 0.27 e Å3
Crystal data top
C23H27F3N2OS2+·2C4H3O4γ = 92.774 (3)°
Mr = 666.66V = 1556.63 (10) Å3
Triclinic, P1Z = 2
a = 6.4175 (2) ÅCu Kα radiation
b = 9.6185 (4) ŵ = 1.59 mm1
c = 25.5771 (10) ÅT = 295 K
α = 96.377 (4)°0.53 × 0.17 × 0.12 mm
β = 96.295 (3)°
Data collection top
Oxford Diffraction Xcalibur Ruby Gemini
diffractometer
11625 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2007)
9926 reflections with i > 2σ(i)
Tmin = 0.643, Tmax = 1.000Rint = 0.000
11625 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05512 restraints
wR(F2) = 0.162H-atom parameters constrained
S = 1.03Δρmax = 0.47 e Å3
11625 reflectionsΔρmin = 0.27 e Å3
430 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
xyzUiso*/UeqOcc. (<1)
S10.28261 (7)0.43649 (6)0.60072 (2)0.0659 (2)
F1A0.4612 (4)0.9150 (2)0.57634 (7)0.1255 (9)0.873 (2)
F2A0.4440 (3)0.8145 (2)0.49990 (8)0.0980 (7)0.873 (2)
F3A0.2283 (3)0.9651 (2)0.51652 (13)0.1469 (15)0.873 (2)
O11.32172 (19)0.39302 (13)0.98491 (5)0.0546 (4)
N10.66238 (16)0.39316 (11)0.79768 (4)0.0305 (3)
N20.91809 (17)0.37193 (11)0.89824 (4)0.0306 (3)
C10.1779 (2)0.48863 (17)0.64991 (6)0.0438 (4)
C20.1109 (3)0.56962 (18)0.60557 (6)0.0477 (5)
C30.2459 (3)0.66960 (18)0.58916 (7)0.0516 (5)
C40.1775 (3)0.7513 (2)0.55001 (8)0.0582 (6)
C50.0262 (3)0.7307 (2)0.52472 (8)0.0656 (7)
C60.1606 (3)0.6297 (2)0.53930 (8)0.0651 (7)
C70.0948 (3)0.55110 (19)0.58004 (7)0.0521 (5)
C80.3238 (3)0.8631 (2)0.53587 (8)0.0680 (7)
C90.1214 (3)0.3095 (2)0.62478 (7)0.0547 (5)
C100.2118 (4)0.1745 (2)0.62336 (9)0.0729 (7)
C110.0916 (4)0.0699 (2)0.64065 (10)0.0856 (9)
C120.1184 (4)0.0977 (2)0.65792 (9)0.0724 (8)
C130.2079 (3)0.23213 (19)0.66001 (7)0.0562 (6)
C140.0877 (3)0.34244 (18)0.64521 (6)0.0477 (5)
C150.3059 (2)0.54985 (16)0.69190 (6)0.0451 (5)
C160.3723 (2)0.49081 (16)0.74246 (6)0.0429 (4)
C170.6030 (2)0.45802 (15)0.74784 (5)0.0371 (4)
C180.8816 (2)0.34649 (14)0.79991 (5)0.0341 (3)
C190.9388 (2)0.27621 (13)0.84905 (5)0.0340 (4)
C200.6999 (2)0.42049 (14)0.89560 (5)0.0340 (3)
C210.6437 (2)0.49041 (13)0.84642 (5)0.0337 (4)
C220.9676 (2)0.30256 (14)0.94779 (6)0.0382 (4)
C231.1958 (3)0.27466 (16)0.95978 (6)0.0461 (5)
F3B0.268 (2)0.8830 (13)0.4868 (3)0.1469 (15)0.127 (2)
F1B0.304 (2)0.9803 (8)0.5651 (4)0.1255 (9)0.127 (2)
F2B0.5195 (10)0.8365 (13)0.5404 (5)0.0980 (7)0.127 (2)
O1A0.35437 (16)0.18909 (10)0.79446 (5)0.0436 (3)
O2A0.60481 (16)0.05328 (11)0.77149 (6)0.0524 (4)
O3A0.02774 (18)0.30289 (11)0.78941 (6)0.0588 (4)
O4A0.25463 (17)0.18840 (12)0.77479 (7)0.0663 (5)
C1A0.4234 (2)0.07131 (14)0.78390 (6)0.0364 (4)
C2A0.2834 (2)0.05762 (14)0.78550 (6)0.0385 (4)
C3A0.0781 (2)0.06083 (14)0.78089 (6)0.0383 (4)
C4A0.0509 (2)0.19431 (14)0.78216 (7)0.0422 (4)
O1B0.24341 (15)0.57369 (10)0.90547 (4)0.0412 (3)
O2B0.01770 (15)0.70858 (11)0.92034 (5)0.0456 (3)
O3B0.55830 (18)1.06667 (11)0.90607 (7)0.0639 (5)
O4B0.84275 (17)0.95113 (12)0.91559 (7)0.0623 (5)
C1B0.1684 (2)0.69183 (13)0.91202 (5)0.0337 (4)
C2B0.3074 (2)0.82060 (14)0.91032 (6)0.0391 (4)
C3B0.5119 (2)0.82417 (13)0.91468 (6)0.0362 (4)
C4B0.6382 (2)0.95740 (14)0.91189 (7)0.0424 (4)
H1A0.573800.316400.797700.0370*
H5A0.071500.784600.498100.0790*
H2A1.009300.448000.899600.0370*
H3A0.384400.681800.604700.0620*
H11.326300.452700.964500.0820*
H12A0.200200.026000.668200.0870*
H13A0.350300.249800.671400.0670*
H15A0.360100.640000.689300.0540*
H16A0.286700.405700.743900.0510*
H6A0.296100.613800.521900.0780*
H10A0.352800.154800.610800.0870*
H11A0.152800.019700.640600.1030*
H18A0.978700.426900.799800.0410*
H18B0.894400.281500.768800.0410*
H19A0.847600.192300.848000.0410*
H19B1.082200.248400.849700.0410*
H20A0.687800.486000.926600.0410*
H20B0.601400.340900.895900.0410*
H21A0.500900.519500.845800.0400*
H21B0.736500.573400.847100.0400*
H22A0.925500.361800.977600.0460*
H22B0.884500.214400.944300.0460*
H23A1.206800.200100.982400.0550*
H23B1.250100.242200.926900.0550*
H16B0.347800.557500.772100.0510*
H17A0.629400.394200.717500.0450*
H17B0.689500.543700.748200.0450*
H2AA0.347100.140900.790100.0460*
H3AA0.010800.021400.776700.0460*
H4A0.284000.107400.771800.0990*
H2BA0.243200.903800.905800.0470*
H3BA0.580200.742700.919600.0430*
H4B0.873700.871100.919800.0930*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0438 (2)0.0814 (3)0.0728 (3)0.0019 (2)0.0006 (2)0.0191 (2)
F1A0.170 (2)0.1107 (15)0.0830 (12)0.0800 (15)0.0226 (12)0.0305 (11)
F2A0.1009 (13)0.0998 (12)0.0986 (13)0.0100 (10)0.0312 (10)0.0223 (11)
F3A0.1041 (14)0.0976 (15)0.267 (4)0.0260 (11)0.0317 (17)0.126 (2)
O10.0495 (6)0.0579 (7)0.0531 (6)0.0124 (5)0.0078 (5)0.0118 (5)
N10.0287 (5)0.0269 (5)0.0353 (5)0.0042 (4)0.0045 (4)0.0035 (4)
N20.0294 (5)0.0255 (5)0.0361 (5)0.0052 (4)0.0029 (4)0.0036 (4)
C10.0413 (8)0.0470 (8)0.0442 (7)0.0051 (6)0.0033 (6)0.0112 (6)
C20.0482 (9)0.0500 (8)0.0446 (8)0.0046 (7)0.0014 (6)0.0097 (6)
C30.0498 (9)0.0530 (9)0.0525 (9)0.0025 (7)0.0012 (7)0.0155 (7)
C40.0674 (11)0.0531 (10)0.0563 (10)0.0080 (8)0.0036 (8)0.0175 (8)
C50.0748 (13)0.0643 (11)0.0585 (10)0.0112 (9)0.0086 (9)0.0239 (9)
C60.0575 (11)0.0723 (12)0.0632 (11)0.0093 (9)0.0139 (8)0.0161 (9)
C70.0477 (9)0.0575 (9)0.0508 (9)0.0049 (7)0.0001 (7)0.0096 (7)
C80.0813 (14)0.0591 (11)0.0668 (12)0.0025 (10)0.0049 (10)0.0258 (9)
C90.0535 (10)0.0628 (10)0.0470 (8)0.0071 (8)0.0020 (7)0.0115 (7)
C100.0738 (13)0.0746 (13)0.0660 (12)0.0245 (11)0.0044 (10)0.0145 (10)
C110.112 (2)0.0604 (12)0.0783 (14)0.0293 (12)0.0090 (13)0.0156 (11)
C120.0983 (17)0.0516 (10)0.0644 (12)0.0033 (10)0.0059 (11)0.0127 (9)
C130.0656 (11)0.0499 (9)0.0516 (9)0.0005 (8)0.0009 (8)0.0088 (7)
C140.0534 (9)0.0508 (9)0.0386 (7)0.0028 (7)0.0030 (6)0.0084 (6)
C150.0456 (8)0.0420 (8)0.0477 (8)0.0038 (6)0.0003 (6)0.0109 (6)
C160.0417 (8)0.0444 (8)0.0425 (7)0.0044 (6)0.0009 (6)0.0081 (6)
C170.0380 (7)0.0363 (7)0.0372 (7)0.0030 (5)0.0030 (5)0.0086 (5)
C180.0300 (6)0.0335 (6)0.0390 (6)0.0002 (5)0.0084 (5)0.0020 (5)
C190.0322 (7)0.0283 (6)0.0407 (7)0.0011 (5)0.0048 (5)0.0003 (5)
C200.0301 (6)0.0337 (6)0.0382 (6)0.0014 (5)0.0078 (5)0.0021 (5)
C210.0320 (7)0.0287 (6)0.0396 (7)0.0015 (5)0.0045 (5)0.0010 (5)
C220.0410 (8)0.0324 (6)0.0406 (7)0.0061 (5)0.0016 (5)0.0085 (5)
C230.0504 (9)0.0390 (7)0.0479 (8)0.0036 (6)0.0044 (6)0.0099 (6)
F3B0.1041 (14)0.0976 (15)0.267 (4)0.0260 (11)0.0317 (17)0.126 (2)
F1B0.170 (2)0.1107 (15)0.0830 (12)0.0800 (15)0.0226 (12)0.0305 (11)
F2B0.1009 (13)0.0998 (12)0.0986 (13)0.0100 (10)0.0312 (10)0.0223 (11)
O1A0.0335 (5)0.0286 (5)0.0689 (7)0.0024 (4)0.0080 (4)0.0069 (4)
O2A0.0296 (5)0.0373 (5)0.0908 (9)0.0036 (4)0.0150 (5)0.0038 (5)
O3A0.0432 (6)0.0316 (5)0.1042 (10)0.0014 (4)0.0123 (6)0.0179 (6)
O4A0.0322 (6)0.0350 (5)0.1307 (13)0.0056 (4)0.0127 (6)0.0059 (7)
C1A0.0283 (7)0.0299 (6)0.0501 (7)0.0038 (5)0.0012 (5)0.0071 (5)
C2A0.0328 (7)0.0274 (6)0.0561 (8)0.0006 (5)0.0046 (6)0.0101 (5)
C3A0.0327 (7)0.0264 (6)0.0558 (8)0.0015 (5)0.0062 (6)0.0055 (5)
C4A0.0343 (7)0.0295 (6)0.0630 (9)0.0034 (5)0.0104 (6)0.0046 (6)
O1B0.0353 (5)0.0274 (4)0.0616 (6)0.0028 (4)0.0073 (4)0.0085 (4)
O2B0.0287 (5)0.0359 (5)0.0730 (7)0.0039 (4)0.0117 (4)0.0066 (5)
O3B0.0389 (6)0.0322 (5)0.1227 (12)0.0019 (4)0.0075 (6)0.0216 (6)
O4B0.0291 (6)0.0342 (5)0.1242 (12)0.0051 (4)0.0110 (6)0.0134 (6)
C1B0.0293 (7)0.0292 (6)0.0423 (7)0.0045 (5)0.0024 (5)0.0076 (5)
C2B0.0318 (7)0.0266 (6)0.0599 (8)0.0007 (5)0.0047 (6)0.0113 (6)
C3B0.0301 (7)0.0260 (6)0.0522 (8)0.0024 (5)0.0029 (5)0.0071 (5)
C4B0.0305 (7)0.0296 (6)0.0671 (9)0.0037 (5)0.0051 (6)0.0087 (6)
Geometric parameters (Å, º) top
S1—C71.757 (2)C12—C131.382 (3)
S1—C91.758 (2)C13—C141.403 (3)
F1A—C81.319 (3)C15—C161.497 (2)
F1B—C81.301 (9)C16—C171.5233 (18)
F2A—C81.325 (3)C18—C191.5110 (18)
F2B—C81.289 (7)C20—C211.5088 (18)
F3A—C81.297 (3)C22—C231.506 (2)
F3B—C81.304 (8)C3—H3A0.9300
O1—C231.413 (2)C5—H5A0.9300
O1—H10.8200C6—H6A0.9300
O1A—C1A1.2488 (17)C10—H10A0.9300
O2A—C1A1.2548 (17)C11—H11A0.9300
O3A—C4A1.2055 (18)C12—H12A0.9300
O4A—C4A1.3053 (17)C13—H13A0.9300
O4A—H4A0.8200C15—H15A0.9300
O1B—C1B1.2567 (16)C16—H16B0.9700
O2B—C1B1.2507 (16)C16—H16A0.9700
O3B—C4B1.2083 (18)C17—H17A0.9700
O4B—C4B1.3105 (17)C17—H17B0.9700
O4B—H4B0.8200C18—H18B0.9700
N1—C211.4927 (16)C18—H18A0.9700
N1—C181.4944 (17)C19—H19A0.9700
N1—C171.5009 (17)C19—H19B0.9700
N2—C221.5074 (18)C20—H20B0.9700
N2—C201.4943 (17)C20—H20A0.9700
N2—C191.4965 (16)C21—H21B0.9700
N1—H1A0.9100C21—H21A0.9700
N2—H2A0.9100C22—H22B0.9700
C1—C141.482 (2)C22—H22A0.9700
C1—C151.340 (2)C23—H23A0.9700
C1—C21.483 (2)C23—H23B0.9700
C2—C71.401 (3)C1A—C2A1.5028 (19)
C2—C31.393 (3)C2A—C3A1.3084 (18)
C3—C41.387 (3)C3A—C4A1.4990 (19)
C4—C51.388 (3)C2A—H2AA0.9300
C4—C81.494 (3)C3A—H3AA0.9300
C5—C61.377 (3)C1B—C2B1.4984 (18)
C6—C71.395 (3)C2B—C3B1.3033 (18)
C9—C101.391 (3)C3B—C4B1.4956 (19)
C9—C141.394 (3)C2B—H2BA0.9300
C10—C111.379 (3)C3B—H3BA0.9300
C11—C121.375 (4)
C7—S1—C9100.77 (9)C10—C11—H11A120.00
C23—O1—H1110.00C11—C12—H12A120.00
C4A—O4A—H4A109.00C13—C12—H12A120.00
C4B—O4B—H4B109.00C14—C13—H13A119.00
C17—N1—C21112.51 (10)C12—C13—H13A119.00
C17—N1—C18111.12 (10)C1—C15—H15A116.00
C18—N1—C21108.81 (9)C16—C15—H15A116.00
C20—N2—C22109.94 (10)C15—C16—H16B109.00
C19—N2—C22112.35 (10)C17—C16—H16B109.00
C19—N2—C20109.06 (10)H16A—C16—H16B108.00
C18—N1—H1A108.00C15—C16—H16A109.00
C21—N1—H1A108.00C17—C16—H16A109.00
C17—N1—H1A108.00N1—C17—H17B109.00
C22—N2—H2A108.00N1—C17—H17A109.00
C20—N2—H2A108.00H17A—C17—H17B108.00
C19—N2—H2A109.00C16—C17—H17A109.00
C14—C1—C15123.86 (14)C16—C17—H17B109.00
C2—C1—C15120.13 (15)N1—C18—H18B109.00
C2—C1—C14115.96 (13)C19—C18—H18B109.00
C1—C2—C3121.69 (16)H18A—C18—H18B108.00
C3—C2—C7117.77 (16)C19—C18—H18A109.00
C1—C2—C7120.50 (15)N1—C18—H18A109.00
C2—C3—C4121.22 (17)N2—C19—H19B109.00
C3—C4—C5120.28 (18)C18—C19—H19B109.00
C3—C4—C8119.45 (17)H19A—C19—H19B108.00
C5—C4—C8120.27 (18)N2—C19—H19A109.00
C4—C5—C6119.44 (18)C18—C19—H19A109.00
C5—C6—C7120.41 (18)N2—C20—H20B109.00
C2—C7—C6120.82 (17)C21—C20—H20A109.00
S1—C7—C2121.38 (14)H20A—C20—H20B108.00
S1—C7—C6117.70 (15)N2—C20—H20A109.00
F1B—C8—F2B108.3 (8)C21—C20—H20B109.00
F1B—C8—F3B107.2 (7)N1—C21—H21A109.00
F2B—C8—F3B108.1 (8)C20—C21—H21B109.00
F2A—C8—F3A105.9 (2)H21A—C21—H21B108.00
F2A—C8—C4112.33 (17)C20—C21—H21A109.00
F2B—C8—C4115.3 (6)N1—C21—H21B109.00
F1B—C8—C4109.6 (5)N2—C22—H22B109.00
F1A—C8—F2A103.16 (19)C23—C22—H22A109.00
F1A—C8—F3A109.0 (2)H22A—C22—H22B108.00
F1A—C8—C4112.26 (18)C23—C22—H22B109.00
F3A—C8—C4113.45 (18)N2—C22—H22A109.00
F3B—C8—C4108.1 (6)C22—C23—H23A109.00
S1—C9—C14121.65 (14)O1—C23—H23A109.00
S1—C9—C10117.29 (16)O1—C23—H23B109.00
C10—C9—C14121.06 (18)H23A—C23—H23B108.00
C9—C10—C11119.8 (2)C22—C23—H23B109.00
C10—C11—C12120.24 (19)O2A—C1A—C2A117.17 (12)
C11—C12—C13120.02 (19)O1A—C1A—O2A123.74 (13)
C12—C13—C14121.17 (19)O1A—C1A—C2A119.10 (12)
C1—C14—C9120.51 (16)C1A—C2A—C3A124.55 (13)
C9—C14—C13117.48 (17)C2A—C3A—C4A121.36 (12)
C1—C14—C13122.01 (16)O4A—C4A—C3A116.89 (12)
C1—C15—C16127.88 (14)O3A—C4A—O4A120.88 (13)
C15—C16—C17112.50 (11)O3A—C4A—C3A122.23 (12)
N1—C17—C16111.24 (11)C1A—C2A—H2AA118.00
N1—C18—C19111.20 (10)C3A—C2A—H2AA118.00
N2—C19—C18111.35 (10)C4A—C3A—H3AA119.00
N2—C20—C21111.66 (10)C2A—C3A—H3AA119.00
N1—C21—C20110.95 (10)O1B—C1B—O2B123.45 (12)
N2—C22—C23114.20 (11)O2B—C1B—C2B117.50 (11)
O1—C23—C22113.68 (13)O1B—C1B—C2B119.05 (12)
C4—C3—H3A119.00C1B—C2B—C3B124.58 (12)
C2—C3—H3A119.00C2B—C3B—C4B120.93 (12)
C6—C5—H5A120.00O3B—C4B—C3B122.51 (12)
C4—C5—H5A120.00O4B—C4B—C3B116.97 (12)
C7—C6—H6A120.00O3B—C4B—O4B120.52 (13)
C5—C6—H6A120.00C1B—C2B—H2BA118.00
C9—C10—H10A120.00C3B—C2B—H2BA118.00
C11—C10—H10A120.00C2B—C3B—H3BA120.00
C12—C11—H11A120.00C4B—C3B—H3BA120.00
C9—S1—C7—C230.94 (17)C3—C4—C8—F1A29.5 (3)
C9—S1—C7—C6152.85 (15)C3—C4—C8—F2A86.2 (2)
C7—S1—C9—C10152.63 (16)C3—C4—C8—F3A153.7 (2)
C7—S1—C9—C1428.28 (17)C5—C4—C8—F1A149.5 (2)
C18—N1—C17—C16173.66 (11)C5—C4—C8—F2A94.8 (2)
C21—N1—C17—C1664.06 (14)C5—C4—C8—F3A25.4 (3)
C17—N1—C18—C19177.84 (10)C4—C5—C6—C71.7 (3)
C21—N1—C18—C1957.75 (13)C5—C6—C7—S1173.90 (15)
C17—N1—C21—C20178.72 (10)C5—C6—C7—C22.3 (3)
C18—N1—C21—C2057.70 (13)S1—C9—C10—C11178.60 (18)
C20—N2—C19—C1855.99 (13)C14—C9—C10—C112.3 (3)
C22—N2—C19—C18178.15 (10)S1—C9—C14—C13.3 (2)
C19—N2—C20—C2156.27 (13)S1—C9—C14—C13175.63 (13)
C22—N2—C20—C21179.87 (11)C10—C9—C14—C1175.76 (17)
C19—N2—C22—C2369.51 (14)C10—C9—C14—C135.3 (3)
C20—N2—C22—C23168.83 (11)C9—C10—C11—C121.8 (4)
C14—C1—C2—C3146.11 (16)C10—C11—C12—C132.6 (4)
C14—C1—C2—C736.3 (2)C11—C12—C13—C140.6 (3)
C15—C1—C2—C336.4 (2)C12—C13—C14—C1176.62 (17)
C15—C1—C2—C7141.17 (16)C12—C13—C14—C94.5 (3)
C2—C1—C14—C939.3 (2)C1—C15—C16—C17110.09 (16)
C2—C1—C14—C13139.62 (16)C15—C16—C17—N1177.47 (12)
C15—C1—C14—C9138.10 (16)N1—C18—C19—N258.15 (14)
C15—C1—C14—C1343.0 (2)N2—C20—C21—N158.42 (13)
C2—C1—C15—C16173.11 (14)N2—C22—C23—O181.02 (15)
C14—C1—C15—C164.1 (2)O1A—C1A—C2A—C3A22.3 (2)
C1—C2—C3—C4175.68 (17)O2A—C1A—C2A—C3A157.25 (16)
C7—C2—C3—C42.0 (3)C1A—C2A—C3A—C4A179.16 (14)
C1—C2—C7—S12.1 (2)C2A—C3A—C4A—O3A2.8 (3)
C1—C2—C7—C6178.20 (16)C2A—C3A—C4A—O4A176.90 (16)
C3—C2—C7—S1175.58 (14)O1B—C1B—C2B—C3B16.6 (2)
C3—C2—C7—C60.5 (3)O2B—C1B—C2B—C3B162.92 (15)
C2—C3—C4—C52.7 (3)C1B—C2B—C3B—C4B179.28 (14)
C2—C3—C4—C8176.38 (17)C2B—C3B—C4B—O3B0.7 (3)
C3—C4—C5—C60.8 (3)C2B—C3B—C4B—O4B178.69 (16)
C8—C4—C5—C6178.23 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O1Bi0.822.052.8365 (16)162
N1—H1A···O1A0.911.812.7055 (15)168
N1—H1A···O2A0.912.573.2580 (15)133
N2—H2A···O1Bi0.911.862.7572 (15)167
N2—H2A···O2Bi0.912.523.2230 (15)134
O4A—H4A···O2Aii0.821.732.5406 (16)167
O4B—H4B···O2Bi0.821.742.5497 (16)168
C2A—H2AA···O3A0.932.512.8251 (17)100
C2B—H2BA···O3B0.932.502.8165 (17)100
C16—H16B···O3Aiii0.972.563.2782 (19)131
C17—H17B···O4Aiv0.972.593.4520 (19)148
C19—H19A···O2A0.972.573.2871 (18)131
C19—H19B···O1Ai0.972.413.2461 (17)144
C20—H20A···O1v0.972.443.3877 (18)167
C21—H21A···O1B0.972.413.2098 (16)140
C21—H21B···O2Bi0.972.513.2367 (17)132
C22—H22B···O3Bvi0.972.513.3848 (18)150
C22—H22B···O4Bvi0.972.553.4236 (18)150
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z; (iii) x, y+1, z; (iv) x+1, y+1, z; (v) x+2, y+1, z+2; (vi) x, y1, z.

Experimental details

Crystal data
Chemical formulaC23H27F3N2OS2+·2C4H3O4
Mr666.66
Crystal system, space groupTriclinic, P1
Temperature (K)295
a, b, c (Å)6.4175 (2), 9.6185 (4), 25.5771 (10)
α, β, γ (°)96.377 (4), 96.295 (3), 92.774 (3)
V3)1556.63 (10)
Z2
Radiation typeCu Kα
µ (mm1)1.59
Crystal size (mm)0.53 × 0.17 × 0.12
Data collection
DiffractometerOxford Diffraction Xcalibur Ruby Gemini
diffractometer
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2007)
Tmin, Tmax0.643, 1.000
No. of measured, independent and
observed [i > 2σ(i)] reflections
11625, 11625, 9926
Rint0.000
(sin θ/λ)max1)0.628
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.162, 1.03
No. of reflections11625
No. of parameters430
No. of restraints12
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.47, 0.27

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O1Bi0.822.052.8365 (16)162
N1—H1A···O1A0.911.812.7055 (15)168
N1—H1A···O2A0.912.573.2580 (15)133
N2—H2A···O1Bi0.911.862.7572 (15)167
N2—H2A···O2Bi0.912.523.2230 (15)134
O4A—H4A···O2Aii0.821.732.5406 (16)167
O4B—H4B···O2Bi0.821.742.5497 (16)168
C2A—H2AA···O3A0.932.512.8251 (17)100
C2B—H2BA···O3B0.932.502.8165 (17)100
C16—H16B···O3Aiii0.972.563.2782 (19)131
C17—H17B···O4Aiv0.972.593.4520 (19)148
C19—H19A···O2A0.972.573.2871 (18)131
C19—H19B···O1Ai0.972.413.2461 (17)144
C20—H20A···O1v0.972.443.3877 (18)167
C21—H21A···O1B0.972.413.2098 (16)140
C21—H21B···O2Bi0.972.513.2367 (17)132
C22—H22B···O3Bvi0.972.513.3848 (18)150
C22—H22B···O4Bvi0.972.553.4236 (18)150
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z; (iii) x, y+1, z; (iv) x+1, y+1, z; (v) x+2, y+1, z+2; (vi) x, y1, z.
 

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