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The title compound, C18H14F4N2O2S·CHCl3, forms a one-dimensional hydrogen-bonded chain via a single O—H...N inter­action; the chain runs approximately along the [110] axis. The two benzene rings are almost parallel to one another, forming a dihedral angle of 8.43 (8)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805027650/bh6024sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805027650/bh6024Isup2.hkl
Contains datablock I

CCDC reference: 287444

Key indicators

  • Single-crystal X-ray study
  • T = 253 K
  • Mean [sigma](C-C) = 0.003 Å
  • Disorder in main residue
  • R factor = 0.047
  • wR factor = 0.089
  • Data-to-parameter ratio = 14.6

checkCIF/PLATON results

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Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C11
Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT213_ALERT_2_C Atom F32 has ADP max/min Ratio ............. 3.20 prolat PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for S1 PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for Cl31 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C19 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.11 PLAT301_ALERT_3_C Main Residue Disorder ......................... 10.00 Perc. PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 43.00 Perc. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C8 - C9 ... 1.45 Ang.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

The title compound, (I), was prepared as an intermediate in the synthesis of Bicalutamide [trademark name for N-(4-cyano-3-trifluoromethyl-phenyl)-3-(4-fluoro-benzensulfonyl)-2-hydroxy-2-methyl-propionamide], a nonsteroidal antiandrogen which acts on the male hormones (androgens) but which has no steroidal effects (Tucker et al., 1988; Xiao et al., 2003).

The crystal structure of (I) comprises one N-(4-cyano-3-trifluoromethyl-phenyl)-3-(4-fluoro-phenyl-sulfanyl)-2-hydroxy-2-methyl-propionamide molecule and one CHCl3 solvent molecule. The solvent molecule is disordered because there are no hydrogen-bonding interactions between CHCl3 and the main moiety. The two benzene ring mean planes are almost parallel to each other, forming a dihedral angle of 8.43 (8)°.

Intermolecular O—H···N hydrogen bonds (Table 2) link the molecules into infinite chains, approximately parallel to the [010] axis. Atom O1 belonging to the hydroxy group acts a donor, while N2 atom of the cyano group serves as an acceptor. Because of this hydrogen-bond interaction, the cyano group deviates slightly from the plane of the benzene ring (C5–C8/C10/C12); the deviations of atoms C9 and N2 from the mean plane are 0.123 and 0.250 Å, respectively. The cyano group is unconjugated with the benzene ring, resulting in a C8—C9 bond length of 1.448 (3) Å, long compared with the value expected for a formal Csp2—Csp bond (Reference for standard value?). The chain is further stabilized by weak intermolecular N1—H1···O1 interactions (Table 2) to form layers in the crystal structure.

Experimental top

2-Hydroxy-2-methyl-3-p-tolylsulfanyl-propionic acid (36.5 g, 159 mmol), 2-trifluoromethyl-4-aminobenzonitrile (38.0 g, 200 mmol) and N,N-dimethyl acetamide (300 ml) were mixed in a 500 ml three-necked bottle and stirred at 263 K. Thionyl chloride (12 ml, 164 mmol) was then added dropwise to the solution and the resulting mixture was kept for 30 min at 258–263 K and then allowed to react for 24 h. After that time, the reaction solution was poured into ice–water (600 ml) and extracted with CH2Cl2 (Volume?). The organic part was washed with HCl (3 M, 4 × 300 ml), NaCl (saturated solution, 2 × 150 ml), NaHCO3 (saturated solution, 3 × 150 ml) and NaCl (saturated solution, 2 × 150 ml), and dried over anhydrous MgSO4. Compound (I) was recovered after vacuum distillation. The final product was recrystallized from a mixture of toluene and petroleum ether (5:1) (yield 26 g, 41%) (Thurlow, 1998; Sepp-Lorenzino & Slovin, 2000). Finally, compound (I) was recrystallized from chloroform, giving colourless crystals suitable for X-ray diffraction.

Refinement top

The Cl atoms of the chloroform molecule and the F atoms of the CF3 group were found to be disordered. Each atom was split over two sites and the site occupancy factors were roughly refined with the sums constrained to 1, and then fixed. H atoms belonging to the hydroxy and amido groups and to the CHCl3 molecule were located in difference maps and included in the refinement with as-found constrained O—H, N—H and C—H bond lengths. Other H atoms were placed in calculated positions and refined using a riding model. Constrained C—H bond lengths are 0.98 Å for aromatic CH, 0.97 Å for methylene CH2 and 0.96 Å for methyl CH3. For all H atoms, Uiso(H) values were refined and then fixed in the final cycles.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: Crystal Structure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: Crystal Structure.

Figures top
[Figure 1] Fig. 1. A view of (I), with displacement ellipsoids drawn at the 30% probability level and H atoms shown as small circles of arbitrary radii. Disordered Cl atoms in the solvent and F atoms in the CF3 group are depicted with open ellipsoids and dashed bonds.
[Figure 2] Fig. 2. A chain of molecules in (I). Hydrogen bonds are represented with dashed lines. [Symmetry codes: (i) 1 + x, 1 + y, z; (ii) −1 + x, −1 + y, z.]
N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-(4-fluorophenylsulfanyl)-2-hydroxy- 2-methylpropionamide chloroform solvate top
Crystal data top
C18H14F4N2O2S·CHCl3Z = 2
Mr = 517.75F(000) = 524.00
Triclinic, P1Dx = 1.561 Mg m3
Hall symbol: -P 1Melting point: 390(1) K
a = 8.8442 (9) ÅMo Kα radiation, λ = 0.7107 Å
b = 10.4591 (9) ÅCell parameters from 4876 reflections
c = 13.319 (1) Åθ = 2.2–27.5°
α = 110.718 (4)°µ = 0.56 mm1
β = 90.895 (2)°T = 253 K
γ = 105.595 (2)°Block, colourless
V = 1101.5 (2) Å30.42 × 0.33 × 0.28 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer
3260 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.025
ω scansθmax = 27.5°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1111
Tmin = 0.738, Tmax = 0.854k = 1313
9744 measured reflectionsl = 1717
4896 independent reflections
Refinement top
Refinement on F2H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.047 w = 1/[0.0002Fo2 + 3σ(Fo2) + 0.5]/(4Fo2)
wR(F2) = 0.089(Δ/σ)max = 0.010
S = 0.96Δρmax = 0.39 e Å3
4892 reflectionsΔρmin = 0.38 e Å3
334 parameters
Crystal data top
C18H14F4N2O2S·CHCl3γ = 105.595 (2)°
Mr = 517.75V = 1101.5 (2) Å3
Triclinic, P1Z = 2
a = 8.8442 (9) ÅMo Kα radiation
b = 10.4591 (9) ŵ = 0.56 mm1
c = 13.319 (1) ÅT = 253 K
α = 110.718 (4)°0.42 × 0.33 × 0.28 mm
β = 90.895 (2)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer
4896 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
3260 reflections with F2 > 2σ(F2)
Tmin = 0.738, Tmax = 0.854Rint = 0.025
9744 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.047334 parameters
wR(F2) = 0.089H-atom parameters constrained
S = 0.96Δρmax = 0.39 e Å3
4892 reflectionsΔρmin = 0.38 e Å3
Special details top

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl111.2062 (2)0.8504 (2)0.4380 (1)0.0960 (5)0.70
Cl121.1429 (8)0.8661 (8)0.4300 (6)0.172 (3)0.30
Cl211.0358 (2)0.9036 (2)0.6305 (1)0.1095 (5)0.80
Cl221.017 (2)0.923 (1)0.5951 (6)0.166 (4)0.20
Cl310.9634 (3)0.6151 (2)0.4646 (2)0.1167 (8)0.50
Cl320.9101 (3)0.6728 (2)0.4393 (2)0.1071 (7)0.50
S10.29974 (8)0.17911 (6)0.16587 (5)0.0675 (2)
F40.5753 (2)0.7802 (1)0.4490 (1)0.1209 (7)
F111.0834 (8)0.0945 (2)0.1285 (6)0.117 (2)0.60
F121.114 (1)0.0985 (3)0.1135 (7)0.078 (2)0.40
F211.2803 (3)0.272 (1)0.0626 (8)0.069 (2)0.40
F221.2746 (3)0.2951 (7)0.0757 (6)0.131 (2)0.60
F311.092 (1)0.276 (1)0.1613 (5)0.117 (2)0.70
F321.041 (2)0.234 (2)0.1663 (8)0.106 (4)0.30
O10.4501 (1)0.0655 (1)0.09616 (9)0.0475 (4)
O20.6803 (2)0.2435 (1)0.3121 (1)0.0509 (4)
N10.7076 (2)0.1402 (1)0.1344 (1)0.0418 (4)
N21.3224 (2)0.6270 (2)0.0573 (2)0.0659 (6)
C10.3477 (2)0.0824 (2)0.2440 (2)0.0505 (6)
C20.4850 (2)0.0225 (2)0.2082 (1)0.0399 (5)
C30.5171 (3)0.0599 (2)0.2764 (2)0.0530 (6)
C40.6341 (2)0.1476 (2)0.2239 (1)0.0382 (5)
C50.8428 (2)0.2384 (2)0.1241 (1)0.0378 (5)
C60.9007 (2)0.3776 (2)0.1980 (1)0.0485 (6)
C71.0292 (2)0.4711 (2)0.1784 (1)0.0491 (6)
C81.1023 (2)0.4287 (2)0.0867 (1)0.0393 (5)
C91.2283 (2)0.5361 (2)0.0681 (2)0.0471 (6)
C101.0473 (2)0.2868 (2)0.0147 (1)0.0378 (5)
C111.1237 (2)0.2332 (1)0.0851 (2)0.0539 (7)
C120.9196 (2)0.1936 (2)0.0341 (1)0.0389 (5)
C130.3847 (2)0.3598 (2)0.2522 (2)0.0517 (6)
C140.3347 (3)0.4153 (3)0.3517 (2)0.0672 (8)
C150.3985 (3)0.5561 (3)0.4186 (2)0.0731 (9)
C160.5099 (4)0.6404 (3)0.3832 (2)0.0784 (9)
C170.5615 (3)0.5922 (3)0.2851 (2)0.080 (1)
C180.4983 (3)0.4503 (3)0.2190 (2)0.0656 (8)
C191.0889 (3)0.7859 (2)0.5206 (2)0.0822 (9)
H20.37490.14680.31910.058*
H30.25520.00350.23730.058*
H60.85090.40990.26390.053*
H71.06900.56970.23070.053*
H120.88230.09400.01660.044*
H140.25190.35270.37540.082*
H150.36360.59400.48980.090*
H170.64270.65680.26190.102*
H180.53390.41370.14790.085*
H191.12780.73740.55880.094*
H310.54500.00310.35090.064*
H320.60290.09800.25140.065*
H330.42420.13680.26960.065*
H1010.41670.15950.08340.053*
H1110.66550.06610.07700.045*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl110.094 (1)0.101 (1)0.092 (1)0.0254 (8)0.0354 (7)0.0359 (7)
Cl120.255 (8)0.203 (5)0.158 (4)0.140 (5)0.101 (5)0.126 (4)
Cl210.0899 (8)0.129 (1)0.0675 (9)0.0435 (8)0.0094 (6)0.0205 (9)
Cl220.26 (1)0.196 (7)0.101 (6)0.152 (7)0.082 (6)0.058 (5)
Cl310.124 (2)0.101 (2)0.080 (1)0.008 (1)0.030 (1)0.002 (1)
Cl320.079 (1)0.114 (2)0.069 (1)0.006 (1)0.0094 (9)0.010 (1)
S10.0756 (4)0.0606 (4)0.0607 (4)0.0246 (3)0.0138 (3)0.0134 (3)
F40.172 (2)0.0521 (9)0.116 (1)0.016 (1)0.010 (1)0.0183 (9)
F110.117 (4)0.061 (3)0.102 (4)0.021 (2)0.071 (3)0.022 (2)
F120.132 (6)0.060 (4)0.077 (4)0.070 (4)0.047 (4)0.035 (4)
F210.036 (4)0.115 (5)0.075 (4)0.042 (4)0.017 (3)0.040 (4)
F220.087 (4)0.102 (3)0.123 (5)0.024 (3)0.068 (3)0.018 (3)
F310.154 (4)0.187 (6)0.077 (3)0.104 (4)0.055 (2)0.088 (3)
F320.17 (1)0.16 (1)0.036 (4)0.11 (1)0.050 (5)0.044 (5)
O10.0578 (8)0.0340 (7)0.0381 (7)0.0012 (6)0.0059 (6)0.0096 (6)
O20.0571 (9)0.0470 (8)0.0346 (7)0.0022 (6)0.0040 (6)0.0086 (6)
N10.0437 (9)0.0341 (8)0.0342 (8)0.0009 (7)0.0053 (7)0.0061 (7)
N20.062 (1)0.049 (1)0.078 (1)0.0031 (9)0.008 (1)0.028 (1)
C10.045 (1)0.051 (1)0.050 (1)0.0080 (9)0.009 (1)0.017 (1)
C20.045 (1)0.036 (1)0.033 (1)0.0052 (8)0.0055 (8)0.0121 (8)
C30.062 (1)0.049 (1)0.050 (1)0.011 (1)0.009 (1)0.025 (1)
C40.042 (1)0.036 (1)0.035 (1)0.0087 (8)0.0046 (8)0.0138 (8)
C50.038 (1)0.035 (1)0.036 (1)0.0043 (8)0.0019 (8)0.0127 (8)
C60.052 (1)0.039 (1)0.042 (1)0.0036 (9)0.0110 (9)0.0067 (9)
C70.053 (1)0.031 (1)0.047 (1)0.0002 (9)0.006 (1)0.0055 (9)
C80.035 (1)0.036 (1)0.043 (1)0.0031 (8)0.0042 (8)0.0159 (8)
C90.045 (1)0.040 (1)0.050 (1)0.0050 (9)0.0022 (9)0.0150 (9)
C100.035 (1)0.039 (1)0.039 (1)0.0081 (8)0.0040 (8)0.0154 (8)
C110.056 (2)0.046 (1)0.052 (1)0.006 (1)0.016 (1)0.015 (1)
C120.039 (1)0.0319 (9)0.037 (1)0.0034 (8)0.0003 (8)0.0082 (8)
C130.051 (1)0.056 (1)0.053 (1)0.023 (1)0.004 (1)0.022 (1)
C140.073 (2)0.062 (1)0.071 (2)0.025 (1)0.025 (1)0.026 (1)
C150.100 (2)0.061 (2)0.065 (2)0.038 (1)0.020 (1)0.021 (1)
C160.107 (2)0.051 (2)0.075 (2)0.024 (1)0.003 (2)0.021 (1)
C170.089 (2)0.062 (2)0.103 (2)0.014 (1)0.019 (2)0.051 (2)
C180.074 (2)0.077 (2)0.061 (1)0.034 (1)0.017 (1)0.036 (1)
C190.091 (2)0.088 (2)0.052 (1)0.024 (1)0.012 (1)0.011 (1)
Geometric parameters (Å, º) top
Cl11—C191.711 (3)C7—C81.379 (3)
Cl12—C191.705 (9)C8—C91.448 (3)
Cl21—C191.713 (3)C8—C101.396 (2)
Cl22—C191.72 (1)C10—C111.498 (3)
Cl31—C191.716 (3)C10—C121.374 (3)
Cl32—C191.763 (3)C13—C141.378 (3)
S1—C11.801 (3)C13—C181.379 (3)
S1—C131.769 (2)C14—C151.375 (3)
F4—C161.365 (2)C15—C161.346 (4)
F11—C111.300 (2)C16—C171.358 (4)
F12—C111.302 (4)C17—C181.380 (3)
F21—C111.330 (3)O1—H1010.8978
F22—C111.299 (3)N1—H1110.8599
F31—C111.30 (1)C1—H20.9700
F32—C111.30 (2)C1—H30.9700
O1—C21.425 (2)C3—H310.9600
O2—C41.218 (2)C3—H320.9600
N1—C41.354 (2)C3—H330.9600
N1—C51.396 (2)C6—H60.9800
N2—C91.137 (3)C7—H70.9800
C1—C21.521 (3)C12—H120.9800
C2—C31.525 (3)C14—H140.9800
C2—C41.537 (2)C15—H150.9800
C5—C61.386 (2)C17—H170.9800
C5—C121.385 (3)C18—H180.9800
C6—C71.382 (3)C19—H190.9507
Cl11···Cl212.952 (3)S1···H111vi3.4239
Cl11···Cl222.72 (1)F4···H2x2.9029
Cl11···Cl312.932 (3)F4···H152.5326
Cl11···Cl322.778 (3)F4···H172.5324
Cl11···F4i3.545 (3)F4···H31iv3.1136
Cl12···Cl212.779 (8)F4···H31x3.2373
Cl12···Cl222.44 (1)F4···H32iv3.2913
Cl12···Cl312.875 (9)F4···H33iv3.1998
Cl12···Cl322.508 (8)F11···H3vi3.0473
Cl21···Cl312.932 (2)F11···H122.3382
Cl21···Cl322.769 (2)F12···H3vi3.3537
Cl21···F11ii3.072 (6)F12···H122.4386
Cl21···F12ii3.242 (8)F21···H18i3.1876
Cl21···F32ii3.55 (2)F22···H18i3.3629
Cl22···Cl312.97 (1)F31···H3vi3.4609
Cl22···Cl322.612 (8)F31···H123.4034
Cl22···F11ii3.44 (1)F32···H3vi2.9493
Cl31···C63.470 (3)F32···H123.0241
Cl32···F43.427 (3)O1···H23.2219
Cl32···C63.563 (3)O1···H32.6146
Cl32···C163.506 (4)O1···H12vi3.0102
Cl32···C173.408 (4)O1···H313.2546
S1···F21iii3.52 (1)O1···H322.6212
S1···O13.060 (2)O1···H332.6619
S1···C22.784 (2)O1···H1112.1083
S1···C43.175 (2)O1···H111vi2.5060
S1···C142.750 (2)O2···H22.6333
S1···C182.738 (2)O2···H62.2642
F4···Cl11iii3.545 (3)O2···H15x2.6864
F4···C3iv3.390 (3)O2···H312.7091
F4···C143.581 (3)O2···H323.2406
F4···C152.333 (3)O2···H1113.0010
F4···C172.339 (3)N1···H62.6658
F4···C183.598 (3)N1···H122.5452
F11···Cl21v3.072 (6)N1···H183.5480
F11···Cl22v3.44 (1)N1···H323.3227
F11···F212.077 (7)N1···H1013.3176
F11···F222.184 (7)N1···H101vi3.1782
F11···F312.08 (1)N2···H73.3370
F11···F321.83 (2)N2···H32viii3.4371
F11···C102.332 (5)N2···H33viii2.9483
F11···C122.679 (7)N2···H101viii2.0603
F12···Cl21v3.242 (8)C1···H12vi3.2475
F12···F211.892 (9)C1···H143.0989
F12···F222.043 (8)C1···H312.7011
F12···F312.22 (1)C1···H323.3286
F12···F322.03 (2)C1···H332.6856
F12···C83.569 (6)C1···H1012.8968
F12···C102.329 (7)C2···H22.0465
F12···C122.73 (1)C2···H32.0454
F21···S1i3.52 (1)C2···H312.0574
F21···F312.12 (1)C2···H322.0508
F21···F322.37 (2)C2···H332.0569
F21···N23.392 (9)C2···H1011.9652
F21···C82.880 (8)C2···H1112.4630
F21···C92.858 (9)C3···H22.6817
F21···C102.335 (6)C3···H32.6656
F21···C123.461 (6)C3···H17ix3.3798
F22···F311.89 (1)C3···H1012.4529
F22···F322.19 (2)C3···H1113.4878
F22···N23.194 (7)C4···H22.6363
F22···C82.840 (6)C4···H33.3202
F22···C92.712 (7)C4···H62.7557
F22···C102.357 (5)C4···H183.5846
F22···C123.546 (5)C4···H312.6411
F31···C83.106 (7)C4···H322.6637
F31···C93.230 (7)C4···H333.3184
F31···C102.351 (8)C4···H1013.1346
F31···C123.293 (9)C4···H1111.8956
F32···Cl21v3.55 (2)C5···H62.0625
F32···C83.21 (1)C5···H73.2752
F32···C93.54 (1)C5···H122.0537
F32···C102.27 (1)C5···H101vi3.2803
F32···C123.02 (1)C5···H1111.9360
O1···O1vi3.335 (2)C6···H72.0477
O1···O23.545 (1)C6···H123.2751
O1···N12.575 (2)C6···H183.4473
O1···N1vi3.093 (2)C6···H1113.1739
O1···N2vii2.956 (2)C7···H62.0549
O1···C12.397 (2)C8···H63.2879
O1···C32.440 (3)C8···H72.0470
O1···C42.406 (2)C8···H123.2834
O1···C5vi3.475 (2)C9···H72.5731
O1···C12vi3.364 (2)C9···H18i3.5780
O2···N12.275 (2)C9···H33viii3.4755
O2···C12.913 (2)C9···H101viii3.1040
O2···C22.399 (2)C10···H73.2747
O2···C32.971 (2)C10···H122.0431
O2···C52.897 (2)C11···H122.6157
O2···C62.864 (3)C12···H3vi3.5420
O2···C133.359 (3)C12···H63.2797
O2···C183.538 (4)C12···H101vi3.2113
N1···O1vi3.093 (2)C12···H1112.4742
N1···C13.516 (3)C13···H22.6584
N1···C22.443 (2)C13···H33.5234
N1···C33.435 (3)C13···H142.0433
N1···C62.447 (2)C13···H153.2905
N1···C122.378 (2)C13···H173.2813
N2···O1viii2.956 (2)C13···H182.0499
N2···C3viii3.501 (2)C14···H22.8073
N2···C73.421 (3)C14···H152.0587
N2···C82.583 (3)C14···H15x3.4201
N2···C103.574 (2)C14···H183.2567
C1···C32.506 (4)C15···H142.0408
C1···C42.485 (3)C15···H15x3.3806
C1···C132.792 (3)C15···H173.2558
C1···C143.298 (3)C15···H19iii3.5905
C3···F4ix3.390 (3)C16···H143.2175
C3···N2vii3.501 (2)C16···H152.0333
C3···C42.481 (3)C16···H172.0402
C4···C52.470 (3)C16···H183.2439
C4···C63.005 (3)C16···H33iv3.4211
C4···C133.464 (3)C17···H63.5400
C5···O1vi3.475 (2)C17···H153.2602
C5···C72.393 (2)C17···H182.0524
C5···C82.785 (2)C17···H32iv3.3513
C5···C102.401 (3)C17···H33iv3.4364
C6···C82.407 (3)C18···H63.3301
C6···C102.769 (3)C18···H143.2528
C6···C122.390 (2)C18···H172.0596
C7···C92.421 (3)C19···H14x3.5083
C7···C102.388 (2)C19···H15i3.4879
C7···C122.747 (2)H2···F4x2.9029
C8···C112.523 (2)H3···Cl11vii3.5477
C8···C122.400 (2)H3···Cl12vii3.3996
C9···C102.505 (2)H3···Cl21x3.3079
C9···C112.974 (2)H3···Cl22x3.3646
C9···C18i3.581 (4)H3···F11vi3.0473
C11···C122.471 (3)H3···F12vi3.3537
C12···O1vi3.364 (2)H3···F31vi3.4609
C13···C152.404 (3)H3···F32vi2.9493
C13···C162.730 (3)H3···C12vi3.5420
C13···C172.393 (3)H12···S1vi2.8481
C14···C162.332 (3)H12···O1vi3.0102
C14···C172.730 (4)H12···C1vi3.2475
C14···C182.367 (4)H14···Cl21x3.1371
C15···C15x3.479 (5)H14···Cl22x3.3596
C15···C172.376 (4)H14···Cl31x2.8714
C15···C182.755 (4)H14···Cl32x2.9306
C16···C182.356 (3)H14···C19x3.5083
C18···C9iii3.581 (4)H15···Cl11iii3.5905
Cl11···H3viii3.5477H15···Cl31x3.3327
Cl11···H73.1565H15···Cl32x3.5835
Cl11···H15i3.5905H15···O2x2.6864
Cl11···H192.3246H15···C14x3.4201
Cl11···H31viii3.4236H15···C15x3.3806
Cl11···H33viii2.9960H15···C19iii3.4879
Cl12···H3viii3.3996H17···C3iv3.3798
Cl12···H73.1806H18···F21iii3.1876
Cl12···H192.5129H18···F22iii3.3629
Cl12···H33viii3.3035H18···C9iii3.5780
Cl21···H3x3.3079H19···C15i3.5905
Cl21···H14x3.1371H31···Cl11vii3.4236
Cl21···H192.0506H31···F4ix3.1136
Cl22···H3x3.3646H31···F4x3.2373
Cl22···H14x3.3596H32···F4ix3.2913
Cl22···H192.3115H32···N2vii3.4371
Cl31···H62.7294H32···C17ix3.3513
Cl31···H73.1757H33···Cl11vii2.9960
Cl31···H14x2.8714H33···Cl12vii3.3035
Cl31···H15x3.3327H33···F4ix3.1998
Cl31···H191.7701H33···N2vii2.9483
Cl32···H62.8165H33···C9vii3.4755
Cl32···H73.1100H33···C16ix3.4211
Cl32···H14x2.9306H33···C17ix3.4364
Cl32···H15x3.5835H101···N1vi3.1782
Cl32···H173.2456H101···N2vii2.0603
Cl32···H192.2677H101···C5vi3.2803
S1···H22.2994H101···C9vii3.1040
S1···H32.3010H101···C12vi3.2113
S1···H12vi2.8481H111···S1vi3.4239
S1···H142.8507H111···O1vi2.5060
S1···H182.8401
Cl11—C19—Cl21119.1 (1)C7—C8—C9117.8 (1)
Cl11—C19—Cl22105.2 (4)C10—C8—C9123.4 (2)
Cl11—C19—Cl31117.6 (1)C8—C10—C11121.3 (2)
Cl11—C19—Cl32106.2 (2)C8—C10—C12120.0 (2)
Cl12—C19—Cl21108.7 (3)C12—C10—C11118.7 (1)
Cl12—C19—Cl31114.3 (2)C18—C13—C14118.3 (2)
Cl21—C19—Cl31117.5 (2)C13—C14—C15121.7 (2)
Cl21—C19—Cl32105.6 (2)C13—C18—C17120.4 (2)
Cl22—C19—Cl31119.7 (4)C14—C15—C16118.0 (2)
S1—C1—C2113.6 (2)C15—C16—C17122.9 (2)
C13—S1—C1102.9 (1)C16—C17—C18118.7 (3)
S1—C13—C14121.3 (2)Cl11—C19—H19118.9327
S1—C13—C18120.3 (2)Cl12—C19—H19140.5302
F4—C16—C17118.4 (2)Cl21—C19—H1996.4389
F4—C16—C15118.7 (2)Cl22—C19—H19117.0419
F11—C11—F21104.3 (5)Cl31—C19—H1977.3166
F11—C11—F22114.3 (5)Cl32—C19—H19109.6825
F11—C11—F31106.1 (5)S1—C1—H2108.3710
F12—C11—F22103.5 (6)S1—C1—H3108.4947
F12—C11—F31117.1 (6)H101—O1—C2113.6427
F12—C11—C10112.4 (5)H111—N1—C4115.9415
F21—C11—F31107.7 (6)H111—N1—C5116.2185
F21—C11—F32128.4 (9)H2—C1—C2108.4686
F21—C11—C10111.2 (4)H3—C1—C2108.3745
F22—C11—F32114.8 (8)H3—C1—H2109.4548
F22—C11—C10114.7 (3)C2—C3—H31109.6748
F31—C11—C10114.1 (4)C2—C3—H32109.1022
F32—C11—C10108.3 (7)C2—C3—H33109.6251
O1—C2—C1108.9 (2)H32—C3—H31109.4779
O1—C2—C4108.6 (1)H33—C3—H31109.4741
O1—C2—C3111.6 (1)H33—C3—H32109.4726
O2—C4—C2120.6 (2)C5—C6—H6120.3401
O2—C4—N1124.2 (2)C5—C12—H12119.5708
N1—C4—C2115.2 (1)C6—C7—H7119.2658
C5—N1—C4127.8 (1)H6—C6—C7119.9811
N1—C5—C6123.2 (2)H7—C7—C8119.3980
N1—C5—C12117.6 (1)C10—C12—H12119.4789
N2—C9—C8175.4 (2)C13—C14—H14119.1366
C1—C2—C4108.7 (2)C13—C18—H18119.7595
C1—C2—C3110.7 (2)H14—C14—C15119.2082
C4—C2—C3108.3 (2)C14—C15—H15120.9946
C12—C5—C6119.2 (2)H15—C15—C16121.0356
C5—C6—C7119.7 (2)C16—C17—H17120.6299
C5—C12—C10121.0 (1)H17—C17—C18120.6217
C6—C7—C8121.3 (1)C17—C18—H18119.8896
C7—C8—C10118.7 (2)
C13—S1—C1—C2102.3 (1)C7—C8—C10—C11178.6 (2)
C1—S1—C13—C1462.2 (2)C8—C10—C11—F11164.7 (4)
C5—N1—C4—O22.0 (4)C8—C10—C11—F12149.4 (5)
C5—N1—C4—C2179.0 (2)C8—C10—C11—F2148.0 (6)
C4—N1—C5—C616.9 (3)C8—C10—C11—F2231.6 (5)
S1—C1—C2—O156.0 (2)C8—C10—C11—F3174.2 (4)
O1—C2—C4—O2174.4 (2)C8—C10—C11—F3298.1 (9)
O1—C2—C4—N16.6 (3)C8—C10—C12—C50.6 (3)
C1—C2—C4—O256.1 (3)S1—C13—C14—C15179.1 (3)
C1—C2—C4—N1124.9 (2)S1—C13—C18—C17178.2 (3)
N1—C5—C6—C7175.7 (2)C13—C14—C15—C161.5 (5)
N1—C5—C12—C10175.7 (2)C14—C15—C16—F4179.6 (3)
C5—C6—C7—C80.4 (4)F4—C16—C17—C18178.7 (3)
C6—C7—C8—C9175.3 (2)C16—C17—C18—C130.2 (4)
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z+1; (iii) x1, y, z; (iv) x, y+1, z; (v) x, y1, z1; (vi) x+1, y, z; (vii) x1, y1, z; (viii) x+1, y+1, z; (ix) x, y1, z; (x) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H101···N2vii0.902.062.957 (3)175
N1—H111···O1vi0.862.513.094 (3)126
Symmetry codes: (vi) x+1, y, z; (vii) x1, y1, z.

Experimental details

Crystal data
Chemical formulaC18H14F4N2O2S·CHCl3
Mr517.75
Crystal system, space groupTriclinic, P1
Temperature (K)253
a, b, c (Å)8.8442 (9), 10.4591 (9), 13.319 (1)
α, β, γ (°)110.718 (4), 90.895 (2), 105.595 (2)
V3)1101.5 (2)
Z2
Radiation typeMo Kα
µ (mm1)0.56
Crystal size (mm)0.42 × 0.33 × 0.28
Data collection
DiffractometerRigaku R-AXIS RAPID
diffractometer
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.738, 0.854
No. of measured, independent and
observed [F2 > 2σ(F2)] reflections
9744, 4896, 3260
Rint0.025
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.089, 0.96
No. of reflections4892
No. of parameters334
No. of restraints?
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.39, 0.38

Computer programs: PROCESS-AUTO (Rigaku, 1998), PROCESS-AUTO, Crystal Structure (Rigaku/MSC, 2004), SIR97 (Altomare et al., 1999), CRYSTALS (Betteridge et al., 2003), ORTEP-3 for Windows (Farrugia, 1997), Crystal Structure.

Selected bond lengths (Å) top
S1—C11.801 (3)O2—C41.218 (2)
S1—C131.769 (2)N2—C91.137 (3)
O1—C21.425 (2)C8—C91.448 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H101···N2i0.902.062.957 (3)175
N1—H111···O1ii0.862.513.094 (3)126
Symmetry codes: (i) x1, y1, z; (ii) x+1, y, z.
 

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