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The title compound, C18H20F3N2OS+·Cl, was synthesized from 2-acetothio­phene, 1-[3-(trifluoro­meth­yl)phen­yl]­piperazine and paraformaldehyde. There are two independent ion pairs in the asymmetric unit. In each cation, the piperazine ring adopts a chair conformation and the F atoms of the trifluoro­methyl groups are disordered over two sites with a ratio of major and minor occupancy of approximately 0.6:0.4. Two inter­molecular N—H...Cl hydrogen bonds help to stabilize the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807029522/lh2431sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807029522/lh2431Isup2.hkl
Contains datablock I

CCDC reference: 655012

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.007 Å
  • Disorder in main residue
  • R factor = 0.062
  • wR factor = 0.187
  • Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C18 PLAT431_ALERT_2_B Short Inter HL..A Contact F2 .. F2 .. 2.45 Ang.
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 43 Perc. PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.10 Ratio PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.84 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for S1 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for S2 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C32 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C12 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C34 PLAT301_ALERT_3_C Main Residue Disorder ......................... 11.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 7 PLAT410_ALERT_2_C Short Intra H...H Contact H9A .. H17A .. 1.94 Ang. PLAT410_ALERT_2_C Short Intra H...H Contact H10B .. H13A .. 1.94 Ang. PLAT410_ALERT_2_C Short Intra H...H Contact H27B .. H31A .. 1.93 Ang. PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 33.20 Deg. F1 -C18 -F1' 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 41.30 Deg. F2' -C18 -F2 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 41.00 Deg. F6' -C36 -F6 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 30.20 Deg. F5 -C36 -F5' 1.555 1.555 1.555
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 156
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 19 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 17 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Mannich bases can be used as anti-corrosion reagents or as a class of selective antidepressants with a low incidence of side effects (Oficialdegui et al., 2000; Martinez et al., 2001; Esparza et al., 2001; Orus et al., 2002). The title compound, was synthesized from 2-acetothiophene, 1-(3-Trifluoromethyl-phenyl)-piperazineand and paraformaldehyde. The molecular structure of the title compound is illustrated in Fig. 1. The asymmetric unit contains two independent molecules. Two intermolecular N—H···Cl hydrogen bonds help to consolidate the crystal packing. In each molecule, the piperazine ring has a chair conformation and the F atoms of the CF3 groups are disordered over two sites.

Related literature top

For background information, see: Oficialdegui et al. (2000); Martinez et al. (2001); Esparza et al. (2001); Orus et al. (2002).

Experimental top

A mixture of 2-acetothiophene 1.26 (10 mmol), 1-(3-Trifluoromethyl-phenyl)-piperazine 2.3 g (15 mmol) and concentrated hydrochloric acid (10 ml) in absolute ethanol(20 ml) was refluxed. Paraformaldehyde 0.9 g (45 mmol) was added over a period of 20 min. The reaction mixture was refluxed for another 12 h, cooled and the solid was precipitated. 20 ml acetone was added to the mixture and stirred for 30 min. The mixture was filtrated, washed with ethyl ether, dried in vacuum to give the title compound. The title compound was dissolved in absolute methanol; the solution was kept at ambient temperature for 15 d by natural evaporation to give single crystals suitable for X-ray analysis.

Refinement top

Carbon-bound H atoms were positioned geometrically, with C—H = 0.93–0.97 Å and Uiso(H) = 1.2 Ueq(C), The nitrogen-bound H atoms were refined freely.

Structure description top

Mannich bases can be used as anti-corrosion reagents or as a class of selective antidepressants with a low incidence of side effects (Oficialdegui et al., 2000; Martinez et al., 2001; Esparza et al., 2001; Orus et al., 2002). The title compound, was synthesized from 2-acetothiophene, 1-(3-Trifluoromethyl-phenyl)-piperazineand and paraformaldehyde. The molecular structure of the title compound is illustrated in Fig. 1. The asymmetric unit contains two independent molecules. Two intermolecular N—H···Cl hydrogen bonds help to consolidate the crystal packing. In each molecule, the piperazine ring has a chair conformation and the F atoms of the CF3 groups are disordered over two sites.

For background information, see: Oficialdegui et al. (2000); Martinez et al. (2001); Esparza et al. (2001); Orus et al. (2002).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of one of the cations drawn with 30% probability ellipsoids.
1-[2-(2-Thienylcarbonyl)ethyl]-4-[3-(trifluoromethyl)phenyl]piperazin-1-ium chloride top
Crystal data top
C18H20F3N2OS+·ClF(000) = 1680
Mr = 404.89Dx = 1.386 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3440 reflections
a = 10.5715 (14) Åθ = 2.3–22.6°
b = 10.4989 (14) ŵ = 0.34 mm1
c = 34.966 (8) ÅT = 294 K
β = 90.040 (6)°Block, colorless
V = 3880.8 (12) Å30.20 × 0.14 × 0.12 mm
Z = 8
Data collection top
Bruker SMART CCD
diffractometer
7997 independent reflections
Radiation source: fine-focus sealed tube3476 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.061
φ and ω scansθmax = 26.5°, θmin = 1.2°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 138
Tmin = 0.935, Tmax = 0.960k = 1113
21590 measured reflectionsl = 4333
Refinement top
Refinement on F2156 restraints
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.062 w = 1/[σ2(Fo2) + (0.04P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.187(Δ/σ)max < 0.001
S = 1.00Δρmax = 0.42 e Å3
7997 reflectionsΔρmin = 0.29 e Å3
533 parameters
Crystal data top
C18H20F3N2OS+·ClV = 3880.8 (12) Å3
Mr = 404.89Z = 8
Monoclinic, P21/nMo Kα radiation
a = 10.5715 (14) ŵ = 0.34 mm1
b = 10.4989 (14) ÅT = 294 K
c = 34.966 (8) Å0.20 × 0.14 × 0.12 mm
β = 90.040 (6)°
Data collection top
Bruker SMART CCD
diffractometer
7997 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
3476 reflections with I > 2σ(I)
Tmin = 0.935, Tmax = 0.960Rint = 0.061
21590 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.062156 restraints
wR(F2) = 0.187H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.42 e Å3
7997 reflectionsΔρmin = 0.29 e Å3
533 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
xyzUiso*/UeqOcc. (<1)
S10.87631 (13)0.26060 (17)0.11320 (4)0.0945 (5)
S20.13158 (12)0.17445 (15)0.39331 (4)0.0845 (5)
Cl10.95342 (8)0.50699 (9)0.22049 (3)0.0532 (3)
Cl20.45144 (9)0.43229 (10)0.22268 (3)0.0567 (3)
F40.6149 (10)0.3307 (14)0.0024 (4)0.160 (5)0.59 (2)
F50.4496 (17)0.2631 (12)0.0181 (4)0.154 (4)0.59 (2)
F60.4203 (15)0.3934 (11)0.0185 (3)0.137 (5)0.59 (2)
F4'0.570 (2)0.260 (2)0.0160 (5)0.160 (7)0.41 (2)
F5'0.376 (2)0.2455 (18)0.0130 (5)0.152 (7)0.41 (2)
F6'0.503 (2)0.3963 (16)0.0258 (4)0.129 (6)0.41 (2)
O10.9179 (3)0.1508 (3)0.19011 (9)0.0654 (9)
O20.0775 (3)0.2832 (3)0.31653 (8)0.0616 (8)
N10.7286 (3)0.2251 (3)0.29390 (9)0.0439 (8)
H1A0.669 (3)0.163 (3)0.2889 (11)0.064 (13)*
N20.6407 (3)0.3079 (3)0.36817 (10)0.0554 (9)
N30.2638 (3)0.2183 (3)0.21098 (9)0.0397 (8)
H3A0.330 (3)0.276 (4)0.2164 (12)0.086 (16)*
N40.3515 (3)0.1331 (3)0.13693 (9)0.0492 (9)
C10.7761 (6)0.3490 (6)0.08685 (14)0.100 (2)
H10.78950.36840.06120.120*
C20.6737 (5)0.3892 (5)0.10693 (15)0.0781 (15)
H20.60840.43770.09660.094*
C30.6785 (4)0.3486 (4)0.14507 (12)0.0557 (11)
H30.61670.36810.16300.067*
C40.7836 (4)0.2773 (4)0.15315 (12)0.0538 (11)
C50.8246 (4)0.2186 (4)0.18879 (12)0.0492 (11)
C60.7438 (4)0.2431 (4)0.22355 (11)0.0540 (11)
H6A0.71500.33080.22320.065*
H6B0.66990.18850.22270.065*
C70.8153 (3)0.2185 (4)0.26006 (11)0.0489 (11)
H7A0.85420.13500.25890.059*
H7B0.88200.28130.26290.059*
C80.6711 (4)0.3527 (4)0.29960 (12)0.0545 (11)
H8A0.62610.37770.27660.065*
H8B0.73720.41480.30430.065*
C90.5804 (4)0.3512 (4)0.33305 (12)0.0583 (12)
H9A0.54720.43630.33690.070*
H9B0.50980.29550.32710.070*
C100.7027 (4)0.1857 (4)0.36287 (12)0.0602 (12)
H10A0.63920.12080.35830.072*
H10B0.74790.16340.38610.072*
C110.7940 (4)0.1878 (4)0.32990 (12)0.0551 (11)
H11A0.86160.24780.33530.066*
H11B0.83140.10400.32680.066*
C120.5690 (4)0.3231 (5)0.40204 (14)0.0648 (13)
C130.6025 (5)0.2608 (5)0.43516 (15)0.0832 (16)
H13A0.67170.20620.43500.100*
C140.5359 (6)0.2777 (7)0.46829 (18)0.102 (2)
C150.4349 (7)0.3582 (8)0.4698 (2)0.131 (3)
H15A0.39310.37240.49270.157*
C160.3960 (6)0.4176 (7)0.4372 (2)0.133 (3)
H16A0.32420.46880.43750.159*
C170.4637 (6)0.4017 (6)0.40344 (18)0.108 (2)
H17A0.43790.44450.38150.129*
C180.5752 (7)0.2091 (8)0.5042 (3)0.152 (3)
F10.6814 (12)0.1474 (16)0.5034 (5)0.212 (10)0.40
F20.4798 (13)0.1113 (12)0.5086 (4)0.222 (8)0.40
F30.5516 (15)0.2816 (12)0.5349 (3)0.191 (6)0.40
F1'0.6351 (9)0.0965 (7)0.4965 (2)0.139 (3)0.60
F2'0.4833 (10)0.1807 (13)0.5273 (3)0.231 (5)0.60
F3'0.6644 (7)0.2900 (8)0.5220 (2)0.184 (4)0.60
C190.2390 (5)0.0884 (5)0.41821 (14)0.0835 (16)
H190.23030.07000.44410.100*
C200.3376 (4)0.0491 (4)0.39733 (13)0.0668 (13)
H200.40480.00120.40670.080*
C210.3257 (4)0.0905 (4)0.35889 (12)0.0516 (11)
H210.38520.07280.34000.062*
C220.2179 (4)0.1591 (4)0.35233 (11)0.0476 (10)
C230.1737 (4)0.2176 (4)0.31697 (11)0.0460 (10)
C240.2519 (3)0.1999 (4)0.28165 (11)0.0505 (11)
H24A0.28400.11340.28110.061*
H24B0.32390.25700.28270.061*
C250.1788 (3)0.2249 (4)0.24523 (11)0.0442 (10)
H25A0.11180.16240.24270.053*
H25B0.14010.30860.24650.053*
C260.3225 (4)0.0914 (4)0.20559 (11)0.0498 (11)
H26A0.25710.02850.20100.060*
H26B0.36760.06730.22860.060*
C270.4123 (4)0.0936 (4)0.17252 (11)0.0532 (11)
H27A0.48120.15160.17820.064*
H27B0.44800.00920.16920.064*
C280.2864 (4)0.2552 (4)0.14174 (12)0.0530 (11)
H28A0.23980.27500.11860.064*
H28B0.34860.32190.14570.064*
C290.1965 (4)0.2530 (4)0.17514 (11)0.0532 (11)
H29A0.15790.33630.17810.064*
H29B0.12970.19180.17030.064*
C300.4274 (4)0.1209 (4)0.10424 (12)0.0562 (11)
C310.5111 (5)0.0189 (5)0.10076 (15)0.0978 (19)
H31A0.51730.04090.12030.117*
C320.5852 (6)0.0065 (7)0.0684 (2)0.126 (2)
H32A0.64190.06100.06690.152*
C330.5778 (6)0.0897 (7)0.03866 (17)0.104 (2)
H33A0.62670.07940.01680.125*
C340.4960 (5)0.1886 (6)0.04236 (15)0.0806 (15)
C350.4210 (4)0.2047 (5)0.07409 (13)0.0644 (13)
H35A0.36530.27310.07520.077*
C360.4935 (10)0.2888 (9)0.0119 (2)0.124 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0841 (10)0.1419 (15)0.0576 (9)0.0016 (9)0.0215 (7)0.0117 (9)
S20.0848 (10)0.1166 (12)0.0520 (8)0.0144 (8)0.0242 (7)0.0045 (8)
Cl10.0477 (6)0.0448 (7)0.0672 (8)0.0020 (5)0.0027 (5)0.0029 (5)
Cl20.0492 (6)0.0460 (7)0.0749 (8)0.0021 (5)0.0017 (5)0.0066 (6)
F40.144 (7)0.195 (8)0.142 (8)0.050 (6)0.040 (6)0.054 (6)
F50.176 (10)0.189 (7)0.097 (6)0.023 (8)0.038 (7)0.022 (5)
F60.173 (9)0.129 (6)0.108 (6)0.029 (6)0.059 (6)0.047 (5)
F4'0.167 (10)0.201 (11)0.111 (9)0.018 (8)0.069 (8)0.027 (7)
F5'0.152 (10)0.177 (10)0.127 (9)0.019 (8)0.020 (8)0.025 (7)
F6'0.169 (11)0.117 (8)0.100 (7)0.012 (8)0.004 (8)0.035 (6)
O10.0550 (18)0.066 (2)0.075 (2)0.0076 (16)0.0098 (16)0.0073 (17)
O20.0543 (18)0.064 (2)0.066 (2)0.0113 (16)0.0070 (15)0.0064 (16)
N10.0398 (19)0.039 (2)0.053 (2)0.0027 (17)0.0023 (16)0.0015 (17)
N20.056 (2)0.057 (2)0.053 (2)0.0002 (18)0.0019 (18)0.0038 (19)
N30.0378 (18)0.039 (2)0.042 (2)0.0011 (16)0.0020 (15)0.0046 (15)
N40.059 (2)0.050 (2)0.038 (2)0.0023 (17)0.0003 (17)0.0005 (16)
C10.119 (5)0.144 (6)0.037 (3)0.031 (4)0.010 (3)0.002 (3)
C20.087 (4)0.086 (4)0.061 (4)0.018 (3)0.008 (3)0.005 (3)
C30.063 (3)0.055 (3)0.049 (3)0.013 (2)0.007 (2)0.000 (2)
C40.049 (3)0.064 (3)0.048 (3)0.014 (2)0.007 (2)0.009 (2)
C50.043 (2)0.048 (3)0.057 (3)0.012 (2)0.005 (2)0.010 (2)
C60.046 (2)0.063 (3)0.054 (3)0.000 (2)0.009 (2)0.001 (2)
C70.040 (2)0.050 (3)0.057 (3)0.0002 (19)0.002 (2)0.004 (2)
C80.060 (3)0.038 (3)0.066 (3)0.005 (2)0.006 (2)0.002 (2)
C90.063 (3)0.047 (3)0.065 (3)0.009 (2)0.007 (2)0.006 (2)
C100.066 (3)0.070 (3)0.045 (3)0.010 (2)0.002 (2)0.011 (2)
C110.055 (2)0.062 (3)0.048 (3)0.010 (2)0.006 (2)0.011 (2)
C120.057 (3)0.075 (3)0.062 (3)0.012 (2)0.006 (2)0.015 (3)
C130.072 (3)0.122 (4)0.056 (3)0.004 (3)0.008 (3)0.001 (3)
C140.094 (4)0.153 (6)0.061 (4)0.004 (4)0.009 (3)0.003 (4)
C150.125 (5)0.179 (7)0.088 (5)0.010 (5)0.029 (4)0.033 (5)
C160.117 (5)0.161 (6)0.120 (6)0.040 (4)0.031 (5)0.021 (5)
C170.116 (4)0.119 (5)0.088 (4)0.039 (4)0.023 (3)0.013 (4)
C180.120 (6)0.194 (8)0.142 (7)0.012 (6)0.045 (6)0.013 (6)
F10.210 (12)0.231 (13)0.194 (12)0.015 (9)0.021 (8)0.046 (9)
F20.255 (12)0.207 (11)0.205 (12)0.011 (9)0.029 (9)0.011 (9)
F30.234 (10)0.224 (10)0.114 (8)0.061 (9)0.019 (8)0.005 (7)
F1'0.169 (6)0.177 (7)0.070 (4)0.007 (6)0.020 (4)0.049 (4)
F2'0.253 (8)0.299 (10)0.141 (7)0.016 (8)0.117 (6)0.045 (7)
F3'0.177 (6)0.250 (8)0.126 (6)0.073 (6)0.054 (5)0.071 (5)
C190.111 (4)0.099 (4)0.040 (3)0.001 (3)0.001 (3)0.003 (3)
C200.078 (3)0.069 (3)0.054 (3)0.001 (3)0.006 (3)0.000 (3)
C210.057 (3)0.052 (3)0.045 (3)0.010 (2)0.006 (2)0.004 (2)
C220.048 (2)0.050 (3)0.045 (3)0.003 (2)0.0085 (19)0.004 (2)
C230.044 (2)0.042 (3)0.052 (3)0.006 (2)0.004 (2)0.004 (2)
C240.043 (2)0.066 (3)0.042 (3)0.004 (2)0.0051 (19)0.005 (2)
C250.041 (2)0.045 (3)0.047 (3)0.0006 (18)0.0030 (19)0.0085 (19)
C260.062 (3)0.045 (3)0.042 (3)0.008 (2)0.003 (2)0.009 (2)
C270.061 (3)0.050 (3)0.048 (3)0.013 (2)0.002 (2)0.002 (2)
C280.056 (3)0.056 (3)0.047 (3)0.008 (2)0.001 (2)0.010 (2)
C290.048 (2)0.062 (3)0.050 (3)0.008 (2)0.006 (2)0.011 (2)
C300.067 (3)0.056 (3)0.046 (3)0.004 (2)0.004 (2)0.008 (2)
C310.140 (5)0.089 (4)0.064 (4)0.036 (4)0.034 (3)0.004 (3)
C320.147 (6)0.146 (7)0.086 (5)0.052 (5)0.033 (4)0.014 (5)
C330.118 (5)0.131 (6)0.063 (4)0.009 (4)0.037 (4)0.013 (4)
C340.093 (4)0.095 (4)0.053 (4)0.012 (3)0.019 (3)0.003 (3)
C350.072 (3)0.074 (3)0.047 (3)0.002 (2)0.007 (2)0.003 (3)
C360.169 (9)0.149 (8)0.054 (5)0.003 (7)0.031 (5)0.002 (5)
Geometric parameters (Å, º) top
S1—C11.683 (6)C12—C171.387 (6)
S1—C41.716 (4)C13—C141.367 (7)
S2—C191.692 (5)C13—H13A0.9300
S2—C221.707 (4)C14—C151.363 (8)
F4—C361.397 (14)C14—C181.505 (10)
F5—C361.178 (13)C15—C161.363 (9)
F6—C361.363 (13)C15—H15A0.9300
F4'—C361.303 (15)C16—C171.389 (8)
F5'—C361.58 (2)C16—H16A0.9300
F6'—C361.234 (17)C17—H17A0.9300
O1—C51.218 (4)C18—F11.296 (9)
O2—C231.228 (4)C18—F2'1.298 (8)
N1—C81.484 (5)C18—F31.340 (9)
N1—C111.488 (5)C18—F1'1.368 (8)
N1—C71.499 (5)C18—F3'1.413 (8)
N1—H1A0.93 (3)C18—F21.448 (9)
N2—C121.416 (5)C19—C201.339 (6)
N2—C101.452 (5)C19—H190.9300
N2—C91.456 (5)C20—C211.418 (6)
N3—C261.482 (5)C20—H200.9300
N3—C291.486 (5)C21—C221.367 (5)
N3—C251.499 (4)C21—H210.9300
N3—H3A0.94 (3)C22—C231.458 (5)
N4—C301.403 (5)C23—C241.498 (5)
N4—C271.461 (5)C24—C251.512 (5)
N4—C281.465 (5)C24—H24A0.9700
C1—C21.358 (6)C24—H24B0.9700
C1—H10.9300C25—H25A0.9700
C2—C31.401 (6)C25—H25B0.9700
C2—H20.9300C26—C271.497 (5)
C3—C41.369 (5)C26—H26A0.9700
C3—H30.9300C26—H26B0.9700
C4—C51.456 (6)C27—H27A0.9700
C5—C61.508 (5)C27—H27B0.9700
C6—C71.505 (5)C28—C291.507 (5)
C6—H6A0.9700C28—H28A0.9700
C6—H6B0.9700C28—H28B0.9700
C7—H7A0.9700C29—H29A0.9700
C7—H7B0.9700C29—H29B0.9700
C8—C91.513 (5)C30—C351.375 (6)
C8—H8A0.9700C30—C311.395 (6)
C8—H8B0.9700C31—C321.384 (7)
C9—H9A0.9700C31—H31A0.9300
C9—H9B0.9700C32—C331.359 (8)
C10—C111.504 (5)C32—H32A0.9300
C10—H10A0.9700C33—C341.357 (7)
C10—H10B0.9700C33—H33A0.9300
C11—H11A0.9700C34—C351.375 (6)
C11—H11B0.9700C34—C361.498 (9)
C12—C131.376 (6)C35—H35A0.9300
C1—S1—C491.7 (3)F2'—C18—F241.3 (7)
C19—S2—C2291.3 (2)F3—C18—F2100.7 (9)
C8—N1—C11108.3 (3)F1'—C18—F274.4 (8)
C8—N1—C7113.5 (3)F3'—C18—F2147.5 (11)
C11—N1—C7111.8 (3)F1—C18—C14117.4 (9)
C8—N1—H1A112 (2)F2'—C18—C14115.0 (8)
C11—N1—H1A107 (2)F3—C18—C14110.2 (8)
C7—N1—H1A104 (2)F1'—C18—C14112.1 (7)
C12—N2—C10116.7 (4)F3'—C18—C14105.2 (7)
C12—N2—C9115.8 (4)F2—C18—C14103.7 (8)
C10—N2—C9111.5 (3)C20—C19—S2114.0 (4)
C26—N3—C29108.3 (3)C20—C19—H19123.0
C26—N3—C25113.3 (3)S2—C19—H19123.0
C29—N3—C25112.0 (3)C19—C20—C21110.7 (4)
C26—N3—H3A107 (3)C19—C20—H20124.6
C29—N3—H3A111 (3)C21—C20—H20124.6
C25—N3—H3A105 (3)C22—C21—C20113.2 (4)
C30—N4—C27114.6 (3)C22—C21—H21123.4
C30—N4—C28116.3 (3)C20—C21—H21123.4
C27—N4—C28110.9 (3)C21—C22—C23129.1 (4)
C2—C1—S1112.9 (4)C21—C22—S2110.8 (3)
C2—C1—H1123.5C23—C22—S2120.1 (3)
S1—C1—H1123.5O2—C23—C22120.8 (4)
C1—C2—C3111.7 (5)O2—C23—C24121.1 (4)
C1—C2—H2124.2C22—C23—C24118.1 (4)
C3—C2—H2124.2C23—C24—C25113.0 (3)
C4—C3—C2113.1 (4)C23—C24—H24A109.0
C4—C3—H3123.5C25—C24—H24A109.0
C2—C3—H3123.5C23—C24—H24B109.0
C3—C4—C5130.5 (4)C25—C24—H24B109.0
C3—C4—S1110.6 (3)H24A—C24—H24B107.8
C5—C4—S1118.9 (3)N3—C25—C24111.0 (3)
O1—C5—C4121.4 (4)N3—C25—H25A109.4
O1—C5—C6121.9 (4)C24—C25—H25A109.4
C4—C5—C6116.7 (4)N3—C25—H25B109.4
C7—C6—C5111.7 (3)C24—C25—H25B109.4
C7—C6—H6A109.3H25A—C25—H25B108.0
C5—C6—H6A109.3N3—C26—C27110.5 (3)
C7—C6—H6B109.3N3—C26—H26A109.5
C5—C6—H6B109.3C27—C26—H26A109.5
H6A—C6—H6B107.9N3—C26—H26B109.5
N1—C7—C6110.8 (3)C27—C26—H26B109.5
N1—C7—H7A109.5H26A—C26—H26B108.1
C6—C7—H7A109.5N4—C27—C26112.5 (3)
N1—C7—H7B109.5N4—C27—H27A109.1
C6—C7—H7B109.5C26—C27—H27A109.1
H7A—C7—H7B108.1N4—C27—H27B109.1
N1—C8—C9110.7 (3)C26—C27—H27B109.1
N1—C8—H8A109.5H27A—C27—H27B107.8
C9—C8—H8A109.5N4—C28—C29111.9 (3)
N1—C8—H8B109.5N4—C28—H28A109.2
C9—C8—H8B109.5C29—C28—H28A109.2
H8A—C8—H8B108.1N4—C28—H28B109.2
N2—C9—C8112.2 (3)C29—C28—H28B109.2
N2—C9—H9A109.2H28A—C28—H28B107.9
C8—C9—H9A109.2N3—C29—C28110.8 (3)
N2—C9—H9B109.2N3—C29—H29A109.5
C8—C9—H9B109.2C28—C29—H29A109.5
H9A—C9—H9B107.9N3—C29—H29B109.5
N2—C10—C11112.0 (3)C28—C29—H29B109.5
N2—C10—H10A109.2H29A—C29—H29B108.1
C11—C10—H10A109.2C35—C30—C31117.1 (4)
N2—C10—H10B109.2C35—C30—N4122.6 (4)
C11—C10—H10B109.2C31—C30—N4120.3 (4)
H10A—C10—H10B107.9C32—C31—C30120.2 (5)
N1—C11—C10110.7 (3)C32—C31—H31A119.9
N1—C11—H11A109.5C30—C31—H31A119.9
C10—C11—H11A109.5C33—C32—C31122.2 (6)
N1—C11—H11B109.5C33—C32—H32A118.9
C10—C11—H11B109.5C31—C32—H32A118.9
H11A—C11—H11B108.1C34—C33—C32117.1 (5)
C13—C12—C17117.3 (5)C34—C33—H33A121.5
C13—C12—N2120.8 (5)C32—C33—H33A121.5
C17—C12—N2121.8 (5)C33—C34—C35122.6 (5)
C14—C13—C12121.3 (6)C33—C34—C36118.7 (6)
C14—C13—H13A119.4C35—C34—C36118.5 (6)
C12—C13—H13A119.4C30—C35—C34120.8 (5)
C15—C14—C13121.1 (7)C30—C35—H35A119.6
C15—C14—C18118.7 (6)C34—C35—H35A119.6
C13—C14—C18120.2 (6)F5—C36—F6'126.5 (13)
C14—C15—C16119.2 (7)F5—C36—F4'61.7 (9)
C14—C15—H15A120.4F6'—C36—F4'117.1 (15)
C16—C15—H15A120.4F5—C36—F696.4 (12)
C15—C16—C17120.0 (7)F6'—C36—F641.0 (7)
C15—C16—H16A120.0F4'—C36—F6131.8 (10)
C17—C16—H16A120.0F5—C36—F4102.9 (9)
C12—C17—C16121.0 (6)F6'—C36—F474.2 (12)
C12—C17—H17A119.5F4'—C36—F447.5 (9)
C16—C17—H17A119.5F6—C36—F4108.0 (11)
F1—C18—F2'123.1 (13)F5—C36—C34118.6 (11)
F1—C18—F3117.5 (11)F6'—C36—C34111.1 (9)
F2'—C18—F359.5 (7)F4'—C36—C34111.0 (10)
F1—C18—F1'33.2 (9)F6—C36—C34117.1 (7)
F2'—C18—F1'105.7 (8)F4—C36—C34111.9 (8)
F3—C18—F1'137.3 (11)F5—C36—F5'30.2 (10)
F1—C18—F3'74.4 (9)F6'—C36—F5'123.2 (15)
F2'—C18—F3'111.4 (10)F4'—C36—F5'90.5 (14)
F3—C18—F3'55.3 (7)F6—C36—F5'83.0 (12)
F1'—C18—F3'107.3 (8)F4—C36—F5'133.0 (10)
F1—C18—F2104.5 (10)C34—C36—F5'101.7 (10)
C4—S1—C1—C21.0 (4)C22—S2—C19—C200.5 (4)
S1—C1—C2—C31.1 (6)S2—C19—C20—C210.2 (6)
C1—C2—C3—C40.7 (6)C19—C20—C21—C220.3 (6)
C2—C3—C4—C5179.4 (4)C20—C21—C22—C23179.5 (4)
C2—C3—C4—S10.1 (5)C20—C21—C22—S20.6 (4)
C1—S1—C4—C30.6 (4)C19—S2—C22—C210.6 (3)
C1—S1—C4—C5178.9 (4)C19—S2—C22—C23179.6 (3)
C3—C4—C5—O1175.2 (4)C21—C22—C23—O2175.4 (4)
S1—C4—C5—O15.4 (5)S2—C22—C23—O23.3 (5)
C3—C4—C5—C63.2 (6)C21—C22—C23—C242.1 (6)
S1—C4—C5—C6176.3 (3)S2—C22—C23—C24179.2 (3)
O1—C5—C6—C721.4 (6)O2—C23—C24—C2521.7 (5)
C4—C5—C6—C7160.3 (3)C22—C23—C24—C25160.8 (3)
C8—N1—C7—C663.1 (4)C26—N3—C25—C2461.9 (4)
C11—N1—C7—C6174.0 (3)C29—N3—C25—C24175.3 (3)
C5—C6—C7—N1171.9 (3)C23—C24—C25—N3174.6 (3)
C11—N1—C8—C957.8 (4)C29—N3—C26—C2758.7 (4)
C7—N1—C8—C9177.5 (3)C25—N3—C26—C27176.4 (3)
C12—N2—C9—C8170.1 (3)C30—N4—C27—C26172.1 (3)
C10—N2—C9—C853.4 (5)C28—N4—C27—C2653.7 (4)
N1—C8—C9—N256.2 (5)N3—C26—C27—N457.4 (4)
C12—N2—C10—C11169.9 (3)C30—N4—C28—C29173.5 (3)
C9—N2—C10—C1154.0 (5)C27—N4—C28—C2953.1 (4)
C8—N1—C11—C1058.5 (4)C26—N3—C29—C2858.7 (4)
C7—N1—C11—C10175.8 (3)C25—N3—C29—C28175.7 (3)
N2—C10—C11—N157.4 (5)N4—C28—C29—N356.8 (4)
C10—N2—C12—C1330.9 (6)C27—N4—C30—C35145.6 (4)
C9—N2—C12—C13165.2 (4)C28—N4—C30—C3514.0 (6)
C10—N2—C12—C17149.8 (5)C27—N4—C30—C3136.2 (6)
C9—N2—C12—C1715.5 (6)C28—N4—C30—C31167.8 (4)
C17—C12—C13—C141.2 (8)C35—C30—C31—C321.2 (8)
N2—C12—C13—C14178.1 (5)N4—C30—C31—C32179.5 (5)
C12—C13—C14—C150.9 (9)C30—C31—C32—C331.5 (11)
C12—C13—C14—C18179.6 (5)C31—C32—C33—C341.5 (11)
C13—C14—C15—C163.4 (11)C32—C33—C34—C351.3 (9)
C18—C14—C15—C16177.9 (7)C32—C33—C34—C36174.6 (7)
C14—C15—C16—C173.8 (12)C31—C30—C35—C341.0 (7)
C13—C12—C17—C160.7 (9)N4—C30—C35—C34179.3 (4)
N2—C12—C17—C16178.6 (5)C33—C34—C35—C301.1 (8)
C15—C16—C17—C121.8 (11)C36—C34—C35—C30174.8 (6)
C15—C14—C18—F1170.6 (11)C33—C34—C36—F571.9 (16)
C13—C14—C18—F18.2 (13)C35—C34—C36—F5112.1 (14)
C15—C14—C18—F2'32.4 (12)C33—C34—C36—F6'128.6 (14)
C13—C14—C18—F2'148.8 (9)C35—C34—C36—F6'47.5 (17)
C15—C14—C18—F332.4 (11)C33—C34—C36—F4'4 (2)
C13—C14—C18—F3146.4 (9)C35—C34—C36—F4'179.6 (17)
C15—C14—C18—F1'153.2 (8)C33—C34—C36—F6173.2 (12)
C13—C14—C18—F1'28.0 (9)C35—C34—C36—F62.9 (15)
C15—C14—C18—F3'90.5 (8)C33—C34—C36—F447.8 (14)
C13—C14—C18—F3'88.3 (8)C35—C34—C36—F4128.3 (11)
C15—C14—C18—F274.7 (10)C33—C34—C36—F5'98.7 (10)
C13—C14—C18—F2106.5 (9)C35—C34—C36—F5'85.3 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···Cl20.94 (3)2.10 (3)3.025 (3)168 (4)
N1—H1A···Cl1i0.93 (3)2.11 (3)3.033 (3)174 (3)
Symmetry code: (i) x+3/2, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC18H20F3N2OS+·Cl
Mr404.89
Crystal system, space groupMonoclinic, P21/n
Temperature (K)294
a, b, c (Å)10.5715 (14), 10.4989 (14), 34.966 (8)
β (°) 90.040 (6)
V3)3880.8 (12)
Z8
Radiation typeMo Kα
µ (mm1)0.34
Crystal size (mm)0.20 × 0.14 × 0.12
Data collection
DiffractometerBruker SMART CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 1997)
Tmin, Tmax0.935, 0.960
No. of measured, independent and
observed [I > 2σ(I)] reflections
21590, 7997, 3476
Rint0.061
(sin θ/λ)max1)0.628
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.062, 0.187, 1.00
No. of reflections7997
No. of parameters533
No. of restraints156
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.42, 0.29

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···Cl20.94 (3)2.10 (3)3.025 (3)168 (4)
N1—H1A···Cl1i0.93 (3)2.11 (3)3.033 (3)174 (3)
Symmetry code: (i) x+3/2, y1/2, z+1/2.
 

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