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In the title compound, C12H10F3N3O2S, the mol­ecules are linked into two-dimensional networks parallel to (1\overline{1}0) through a mixture of π–π stacking and N—H...N hydrogen-bond inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807014389/bg2038sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807014389/bg2038Isup2.hkl
Contains datablock I

CCDC reference: 646716

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.006 Å
  • Disorder in main residue
  • R factor = 0.063
  • wR factor = 0.171
  • Data-to-parameter ratio = 11.6

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C12 PLAT431_ALERT_2_B Short Inter HL..A Contact F2' .. F2' .. 2.48 Ang.
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) . 200 Ang. PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 400 Deg. PLAT301_ALERT_3_C Main Residue Disorder ......................... 12.00 Perc. PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); 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, 2001); software used to prepare material for publication: SHELXTL.

2-(o-Tolyloxy)-N-[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]acetamide top
Crystal data top
C12H10F3N3O2SZ = 2
Mr = 317.29F(000) = 324
Triclinic, P1Dx = 1.532 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.347 (2) ÅCell parameters from 1768 reflections
b = 9.430 (2) Åθ = 2.3–26.2°
c = 9.493 (2) ŵ = 0.28 mm1
α = 108.030 (4)°T = 298 K
β = 101.762 (4)°Block, yellow
γ = 94.381 (4)°0.30 × 0.26 × 0.15 mm
V = 687.8 (3) Å3
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2061 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.026
Graphite monochromatorθmax = 25.1°, θmin = 2.3°
φ and ω scansh = 99
3448 measured reflectionsk = 1011
2385 independent reflectionsl = 911
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)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.171H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0956P)2 + 0.3695P]
where P = (Fo2 + 2Fc2)/3
2385 reflections(Δ/σ)max < 0.001
205 parametersΔρmax = 0.33 e Å3
22 restraintsΔρmin = 0.31 e Å3
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)
C10.6139 (5)0.3226 (4)0.3743 (5)0.0781 (10)
H1A0.53640.41220.35040.117*
H1B0.72330.34850.37780.117*
H1C0.58500.27660.29730.117*
C20.6091 (4)0.2147 (4)0.5258 (4)0.0596 (8)
C30.5232 (4)0.2544 (5)0.6224 (5)0.0789 (11)
H30.46880.35260.59270.095*
C40.5159 (5)0.1545 (6)0.7592 (5)0.0916 (14)
H40.45820.18460.82170.110*
C50.5943 (6)0.0101 (6)0.8032 (5)0.0894 (13)
H50.58850.05860.89580.107*
C60.6821 (5)0.0360 (4)0.7126 (4)0.0704 (9)
H60.73590.13460.74410.085*
C70.6889 (4)0.0667 (3)0.5740 (3)0.0531 (7)
C80.8403 (4)0.1170 (3)0.5087 (4)0.0518 (7)
H8A0.93280.14550.59740.062*
H8B0.75810.18220.53240.062*
C90.8981 (3)0.1356 (3)0.3752 (4)0.0498 (7)
C101.0265 (4)0.3333 (3)0.3036 (4)0.0512 (7)
C111.1514 (4)0.3840 (3)0.1224 (4)0.0545 (7)
C121.2253 (4)0.3870 (4)0.0068 (4)0.0682 (9)
F11.1245 (4)0.3078 (4)0.1401 (3)0.1025 (11)0.888 (4)
F21.3662 (4)0.3397 (6)0.0004 (5)0.1396 (18)0.888 (4)
F31.2475 (5)0.5245 (3)0.0161 (3)0.1061 (12)0.888 (4)
F1'1.268 (3)0.2499 (14)0.067 (2)0.1025 (11)0.112 (4)
F2'1.3636 (18)0.481 (2)0.030 (2)0.1396 (18)0.112 (4)
F3'1.130 (2)0.410 (2)0.1245 (19)0.1061 (12)0.112 (4)
N10.9516 (3)0.2841 (3)0.3980 (3)0.0558 (6)
H10.936 (4)0.348 (3)0.479 (2)0.060 (9)*
N21.0869 (4)0.4754 (3)0.3417 (3)0.0625 (7)
N31.1607 (3)0.5045 (3)0.2349 (3)0.0620 (7)
O10.7715 (3)0.0337 (2)0.4738 (2)0.0550 (5)
O20.9037 (3)0.0362 (2)0.2612 (3)0.0622 (6)
S11.05329 (10)0.22043 (8)0.13205 (9)0.0570 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.093 (3)0.059 (2)0.077 (2)0.0171 (18)0.023 (2)0.0202 (18)
C20.0537 (17)0.068 (2)0.067 (2)0.0061 (14)0.0170 (15)0.0351 (16)
C30.064 (2)0.097 (3)0.100 (3)0.0068 (19)0.028 (2)0.063 (3)
C40.082 (3)0.143 (4)0.093 (3)0.038 (3)0.051 (2)0.076 (3)
C50.101 (3)0.121 (4)0.071 (2)0.042 (3)0.047 (2)0.044 (2)
C60.084 (2)0.075 (2)0.060 (2)0.0233 (19)0.0311 (18)0.0222 (17)
C70.0520 (16)0.0606 (18)0.0547 (17)0.0092 (13)0.0181 (13)0.0267 (14)
C80.0604 (17)0.0385 (14)0.0586 (17)0.0061 (12)0.0209 (14)0.0152 (13)
C90.0502 (15)0.0399 (14)0.0606 (18)0.0061 (12)0.0164 (13)0.0165 (13)
C100.0545 (16)0.0405 (14)0.0615 (18)0.0070 (12)0.0212 (14)0.0166 (13)
C110.0566 (17)0.0516 (17)0.0566 (18)0.0031 (13)0.0158 (14)0.0195 (14)
C120.078 (2)0.067 (2)0.061 (2)0.0000 (17)0.0240 (18)0.0216 (17)
F10.130 (2)0.103 (2)0.0589 (15)0.0206 (18)0.0282 (15)0.0104 (14)
F20.112 (2)0.247 (5)0.151 (3)0.101 (3)0.089 (2)0.139 (4)
F30.166 (3)0.0744 (16)0.094 (2)0.0044 (17)0.064 (2)0.0344 (14)
F1'0.130 (2)0.103 (2)0.0589 (15)0.0206 (18)0.0282 (15)0.0104 (14)
F2'0.112 (2)0.247 (5)0.151 (3)0.101 (3)0.089 (2)0.139 (4)
F3'0.166 (3)0.0744 (16)0.094 (2)0.0044 (17)0.064 (2)0.0344 (14)
N10.0691 (16)0.0380 (13)0.0626 (16)0.0028 (11)0.0300 (13)0.0121 (11)
N20.0805 (18)0.0409 (13)0.0687 (17)0.0007 (12)0.0335 (14)0.0136 (12)
N30.0744 (17)0.0498 (14)0.0655 (17)0.0003 (12)0.0296 (14)0.0183 (12)
O10.0699 (13)0.0427 (11)0.0553 (12)0.0009 (9)0.0269 (10)0.0149 (9)
O20.0803 (15)0.0435 (11)0.0635 (13)0.0031 (10)0.0296 (11)0.0124 (10)
S10.0663 (5)0.0458 (5)0.0569 (5)0.0014 (3)0.0204 (4)0.0122 (4)
Geometric parameters (Å, º) top
C1—C21.493 (5)C8—H8B0.9700
C1—H1A0.9600C9—O21.205 (4)
C1—H1B0.9600C9—N11.372 (4)
C1—H1C0.9600C10—N21.305 (4)
C2—C31.392 (5)C10—N11.361 (4)
C2—C71.393 (5)C10—S11.716 (3)
C3—C41.364 (6)C11—N31.280 (4)
C3—H30.9300C11—C121.488 (5)
C4—C51.363 (6)C11—S11.727 (3)
C4—H40.9300C12—F21.285 (4)
C5—C61.380 (5)C12—F2'1.315 (9)
C5—H50.9300C12—F3'1.318 (9)
C6—C71.387 (5)C12—F11.324 (4)
C6—H60.9300C12—F31.328 (4)
C7—O11.376 (4)C12—F1'1.349 (9)
C8—O11.402 (3)N1—H10.856 (10)
C8—C91.498 (4)N2—N31.373 (4)
C8—H8A0.9700
C2—C1—H1A109.5H8A—C8—H8B108.2
C2—C1—H1B109.5O2—C9—N1121.8 (3)
H1A—C1—H1B109.5O2—C9—C8126.5 (3)
C2—C1—H1C109.5N1—C9—C8111.7 (2)
H1A—C1—H1C109.5N2—C10—N1120.3 (3)
H1B—C1—H1C109.5N2—C10—S1114.8 (2)
C3—C2—C7117.2 (3)N1—C10—S1124.9 (2)
C3—C2—C1122.5 (3)N3—C11—C12120.8 (3)
C7—C2—C1120.3 (3)N3—C11—S1116.5 (2)
C4—C3—C2122.4 (4)C12—C11—S1122.7 (2)
C4—C3—H3118.8F2'—C12—F3'106.2 (8)
C2—C3—H3118.8F2—C12—F1108.8 (3)
C5—C4—C3119.2 (4)F2—C12—F3106.9 (3)
C5—C4—H4120.4F1—C12—F3103.1 (3)
C3—C4—H4120.4F2'—C12—F1'104.4 (8)
C4—C5—C6121.1 (4)F3'—C12—F1'103.8 (8)
C4—C5—H5119.4F2—C12—C11113.5 (3)
C6—C5—H5119.4F2'—C12—C11115.4 (10)
C5—C6—C7119.1 (4)F3'—C12—C11117.7 (10)
C5—C6—H6120.4F1—C12—C11111.6 (3)
C7—C6—H6120.4F3—C12—C11112.2 (3)
O1—C7—C6124.4 (3)F1'—C12—C11108.0 (10)
O1—C7—C2114.7 (3)C10—N1—C9124.7 (3)
C6—C7—C2121.0 (3)C10—N1—H1120 (2)
O1—C8—C9109.5 (2)C9—N1—H1115 (2)
O1—C8—H8A109.8C10—N2—N3112.5 (3)
C9—C8—H8A109.8C11—N3—N2111.0 (2)
O1—C8—H8B109.8C7—O1—C8117.3 (2)
C9—C8—H8B109.8C10—S1—C1185.24 (14)
C7—C2—C3—C40.1 (5)N3—C11—C12—F320.7 (5)
C1—C2—C3—C4178.4 (4)S1—C11—C12—F3160.5 (3)
C2—C3—C4—C50.5 (6)N3—C11—C12—F1'151.8 (10)
C3—C4—C5—C60.7 (6)S1—C11—C12—F1'26.9 (10)
C4—C5—C6—C70.6 (6)N2—C10—N1—C9173.7 (3)
C5—C6—C7—O1179.6 (3)S1—C10—N1—C95.3 (5)
C5—C6—C7—C20.2 (5)O2—C9—N1—C105.3 (5)
C3—C2—C7—O1179.9 (3)C8—C9—N1—C10172.9 (3)
C1—C2—C7—O11.5 (4)N1—C10—N2—N3178.8 (3)
C3—C2—C7—C60.1 (5)S1—C10—N2—N30.3 (4)
C1—C2—C7—C6178.3 (3)C12—C11—N3—N2179.1 (3)
O1—C8—C9—O27.9 (4)S1—C11—N3—N20.3 (4)
O1—C8—C9—N1174.0 (2)C10—N2—N3—C110.3 (4)
N3—C11—C12—F2100.7 (5)C6—C7—O1—C86.0 (4)
S1—C11—C12—F278.1 (4)C2—C7—O1—C8173.8 (3)
N3—C11—C12—F2'35.4 (12)C9—C8—O1—C7170.2 (2)
S1—C11—C12—F2'143.3 (11)N2—C10—S1—C110.1 (3)
N3—C11—C12—F3'91.3 (11)N1—C10—S1—C11178.9 (3)
S1—C11—C12—F3'90.0 (11)N3—C11—S1—C100.1 (3)
N3—C11—C12—F1135.9 (4)C12—C11—S1—C10178.9 (3)
S1—C11—C12—F145.4 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N2i0.86 (1)2.04 (1)2.885 (4)171 (3)
Symmetry code: (i) x+2, y+1, z+1.
 

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