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In the title compound, C19H15FN4OS, the dihedral angles between the planes of the triazole and the unsubstituted and F-substituted benzene rings are 23.0 (2) and 65.6 (6)°, respectively, while that between the two benzene rings is 87.4 (0)°. There are some intermolecular and intramolecular interactions in the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804013881/na6343sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804013881/na6343Isup2.hkl
Contains datablock I

CCDC reference: 245293

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • R factor = 0.073
  • wR factor = 0.152
  • Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C8 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT432_ALERT_2_C Short Inter X...Y Contact C12 .. C12 .. 3.19 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (sheldrick, 1990); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I) top
Crystal data top
C19H15FN4OSZ = 2
Mr = 366.41F(000) = 380
Triclinic, P1Dx = 1.407 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.3895 (19) ÅCell parameters from 20 reflections
b = 9.6613 (19) Åθ = 2–11°
c = 10.929 (2) ŵ = 0.21 mm1
α = 111.53 (3)°T = 293 K
β = 100.46 (3)°Pillar, yellow
γ = 102.08 (3)°0.20 × 0.20 × 0.18 mm
V = 864.7 (4) Å3
Data collection top
Siemens SMART CCD area detector
diffractometer
2441 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.023
Graphite monochromatorθmax = 25.9°, θmin = 2.1°
ω scansh = 611
3976 measured reflectionsk = 1211
3382 independent reflectionsl = 1313
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)] = 0.073Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152H-atom parameters constrained
S = 1.11 w = 1/[σ2(Fo2) + (0.0597P)2]
where P = (Fo2 + 2Fc2)/3
3382 reflections(Δ/σ)max < 0.001
235 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = 0.27 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*/Ueq
S10.05585 (10)0.82906 (11)0.40511 (8)0.0507 (3)
F10.8244 (3)0.5052 (3)0.4824 (2)0.0781 (7)
O10.3407 (3)0.8580 (3)0.5329 (2)0.0539 (6)
N10.0547 (3)0.7841 (3)0.1577 (2)0.0415 (7)
N20.3586 (3)0.7371 (3)0.1879 (2)0.0315 (6)
N30.3044 (3)0.6014 (3)0.0710 (2)0.0395 (6)
N40.5226 (3)0.7543 (3)0.0708 (3)0.0497 (7)
C10.2066 (4)0.9109 (4)0.0474 (3)0.0488 (9)
H1A0.25600.99550.13160.059*
C20.2426 (4)0.9107 (5)0.0698 (4)0.0636 (11)
H2A0.31730.99470.06420.076*
C30.1682 (5)0.7866 (5)0.1945 (4)0.0674 (11)
H3B0.19260.78650.27330.081*
C40.0583 (5)0.6635 (5)0.2025 (4)0.0636 (11)
H4B0.00770.58010.28720.076*
C50.0215 (4)0.6610 (4)0.0875 (3)0.0506 (9)
H5A0.05370.57680.09400.061*
C60.0976 (3)0.7855 (4)0.0389 (3)0.0385 (7)
C70.0930 (4)0.8051 (5)0.1660 (4)0.0657 (11)
H7A0.17120.72960.08310.079*
H7B0.09260.90900.17520.079*
C80.1248 (4)0.7836 (6)0.2857 (4)0.0813 (14)
H8A0.18450.67670.25860.098*
H8B0.18110.85240.32720.098*
C90.1452 (3)0.7929 (3)0.2735 (3)0.0352 (7)
C100.2870 (3)0.7725 (3)0.2945 (3)0.0336 (7)
C110.4870 (3)0.8239 (4)0.1840 (3)0.0417 (8)
H11A0.54420.92160.25290.050*
C120.4059 (4)0.6208 (4)0.0060 (3)0.0451 (8)
H12A0.39790.54650.08030.054*
C130.3700 (3)0.7876 (3)0.4262 (3)0.0386 (7)
C140.4954 (3)0.7137 (3)0.4322 (3)0.0369 (7)
C150.6273 (4)0.7929 (4)0.5399 (3)0.0458 (8)
H15A0.64040.89410.60220.055*
C160.7388 (4)0.7240 (4)0.5559 (3)0.0525 (9)
H16A0.82830.77810.62700.063*
C170.7154 (4)0.5743 (4)0.4653 (3)0.0506 (9)
C180.5872 (4)0.4906 (4)0.3584 (3)0.0481 (9)
H18A0.57450.38850.29850.058*
C190.4769 (4)0.5614 (4)0.3416 (3)0.0429 (8)
H19A0.38890.50690.26870.051*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0422 (5)0.0638 (6)0.0421 (5)0.0171 (4)0.0178 (4)0.0147 (4)
F10.0785 (16)0.0949 (17)0.0698 (14)0.0539 (15)0.0141 (12)0.0324 (13)
O10.0576 (15)0.0643 (16)0.0310 (12)0.0227 (13)0.0107 (11)0.0091 (11)
N10.0326 (15)0.0513 (17)0.0411 (15)0.0144 (13)0.0094 (12)0.0197 (13)
N20.0306 (14)0.0296 (13)0.0299 (13)0.0077 (11)0.0053 (11)0.0100 (11)
N30.0393 (15)0.0351 (14)0.0356 (14)0.0099 (12)0.0072 (12)0.0081 (12)
N40.0422 (17)0.0562 (19)0.0523 (17)0.0117 (15)0.0194 (14)0.0234 (15)
C10.051 (2)0.043 (2)0.048 (2)0.0110 (17)0.0093 (16)0.0186 (16)
C20.070 (3)0.065 (3)0.082 (3)0.026 (2)0.030 (2)0.052 (2)
C30.083 (3)0.095 (3)0.054 (2)0.048 (3)0.030 (2)0.046 (2)
C40.070 (3)0.074 (3)0.040 (2)0.030 (2)0.0050 (19)0.0168 (19)
C50.046 (2)0.051 (2)0.047 (2)0.0128 (17)0.0030 (16)0.0170 (17)
C60.0336 (18)0.0427 (18)0.0394 (17)0.0150 (15)0.0063 (14)0.0175 (15)
C70.040 (2)0.103 (3)0.069 (3)0.033 (2)0.0180 (19)0.043 (2)
C80.038 (2)0.137 (4)0.059 (2)0.026 (2)0.0142 (19)0.031 (3)
C90.0394 (18)0.0272 (16)0.0314 (16)0.0049 (14)0.0109 (13)0.0064 (13)
C100.0349 (17)0.0321 (16)0.0298 (15)0.0074 (14)0.0094 (13)0.0102 (13)
C110.0346 (18)0.0416 (18)0.0445 (18)0.0069 (15)0.0090 (15)0.0168 (15)
C120.050 (2)0.050 (2)0.0350 (17)0.0215 (18)0.0138 (16)0.0124 (16)
C130.0372 (18)0.0335 (17)0.0367 (17)0.0035 (14)0.0060 (14)0.0116 (14)
C140.0421 (19)0.0350 (17)0.0310 (15)0.0070 (15)0.0065 (14)0.0156 (13)
C150.051 (2)0.0432 (19)0.0380 (18)0.0123 (17)0.0053 (16)0.0162 (15)
C160.046 (2)0.057 (2)0.046 (2)0.0116 (18)0.0011 (16)0.0188 (18)
C170.051 (2)0.067 (2)0.050 (2)0.033 (2)0.0152 (17)0.0333 (19)
C180.066 (2)0.046 (2)0.0380 (17)0.0243 (19)0.0151 (17)0.0197 (16)
C190.050 (2)0.0417 (19)0.0333 (16)0.0106 (16)0.0073 (15)0.0160 (15)
Geometric parameters (Å, º) top
S1—C91.756 (3)C5—C61.389 (4)
S1—C81.799 (4)C5—H5A0.9300
F1—C171.354 (4)C7—C81.470 (5)
O1—C131.229 (3)C7—H7A0.9700
N1—C91.354 (4)C7—H7B0.9700
N1—C61.431 (4)C8—H8A0.9700
N1—C71.457 (4)C8—H8B0.9700
N2—C111.334 (4)C9—C101.377 (4)
N2—N31.365 (3)C10—C131.447 (4)
N2—C101.419 (3)C11—H11A0.9300
N3—C121.310 (4)C12—H12A0.9300
N4—C111.315 (4)C13—C141.503 (4)
N4—C121.349 (4)C14—C151.385 (4)
C1—C61.374 (4)C14—C191.392 (4)
C1—C21.382 (5)C15—C161.371 (4)
C1—H1A0.9300C15—H15A0.9300
C2—C31.374 (5)C16—C171.363 (5)
C2—H2A0.9300C16—H16A0.9300
C3—C41.366 (5)C17—C181.363 (4)
C3—H3B0.9300C18—C191.377 (4)
C4—C51.369 (5)C18—H18A0.9300
C4—H4B0.9300C19—H19A0.9300
C9—S1—C891.51 (16)C7—C8—H8B110.3
C9—N1—C6127.1 (3)S1—C8—H8B110.3
C9—N1—C7115.5 (3)H8A—C8—H8B108.6
C6—N1—C7116.3 (2)N1—C9—C10128.4 (3)
C11—N2—N3108.9 (3)N1—C9—S1111.0 (2)
C11—N2—C10127.6 (2)C10—C9—S1120.5 (2)
N3—N2—C10123.5 (2)C9—C10—N2121.4 (2)
C12—N3—N2101.6 (3)C9—C10—C13121.5 (3)
C11—N4—C12101.4 (3)N2—C10—C13117.1 (3)
C6—C1—C2119.7 (3)N4—C11—N2111.6 (3)
C6—C1—H1A120.1N4—C11—H11A124.2
C2—C1—H1A120.1N2—C11—H11A124.2
C3—C2—C1120.1 (4)N3—C12—N4116.5 (3)
C3—C2—H2A119.9N3—C12—H12A121.8
C1—C2—H2A119.9N4—C12—H12A121.8
C4—C3—C2119.8 (4)O1—C13—C10122.1 (3)
C4—C3—H3B120.1O1—C13—C14119.1 (3)
C2—C3—H3B120.1C10—C13—C14118.7 (3)
C3—C4—C5121.0 (4)C15—C14—C19118.7 (3)
C3—C4—H4B119.5C15—C14—C13119.0 (3)
C5—C4—H4B119.5C19—C14—C13121.9 (3)
C4—C5—C6119.3 (4)C16—C15—C14120.8 (3)
C4—C5—H5A120.3C16—C15—H15A119.6
C6—C5—H5A120.3C14—C15—H15A119.6
C1—C6—C5120.0 (3)C17—C16—C15118.5 (3)
C1—C6—N1121.1 (3)C17—C16—H16A120.7
C5—C6—N1118.8 (3)C15—C16—H16A120.7
N1—C7—C8108.7 (3)F1—C17—C18118.4 (3)
N1—C7—H7A109.9F1—C17—C16118.6 (3)
C8—C7—H7A109.9C18—C17—C16123.0 (3)
N1—C7—H7B109.9C17—C18—C19118.2 (3)
C8—C7—H7B109.9C17—C18—H18A120.9
H7A—C7—H7B108.3C19—C18—H18A120.9
C7—C8—S1106.9 (3)C18—C19—C14120.8 (3)
C7—C8—H8A110.3C18—C19—H19A119.6
S1—C8—H8A110.3C14—C19—H19A119.6
C11—N2—N3—C120.9 (3)C11—N2—C10—C9116.3 (3)
C10—N2—N3—C12179.6 (3)N3—N2—C10—C965.3 (4)
C6—C1—C2—C30.9 (5)C11—N2—C10—C1363.2 (4)
C1—C2—C3—C40.1 (6)N3—N2—C10—C13115.3 (3)
C2—C3—C4—C50.5 (6)C12—N4—C11—N20.8 (3)
C3—C4—C5—C60.2 (5)N3—N2—C11—N40.0 (3)
C2—C1—C6—C51.5 (5)C10—N2—C11—N4178.6 (3)
C2—C1—C6—N1178.2 (3)N2—N3—C12—N41.5 (4)
C4—C5—C6—C11.2 (5)C11—N4—C12—N31.5 (4)
C4—C5—C6—N1177.9 (3)C9—C10—C13—O119.9 (5)
C9—N1—C6—C160.8 (4)N2—C10—C13—O1159.5 (3)
C7—N1—C6—C1106.7 (4)C9—C10—C13—C14159.7 (3)
C9—N1—C6—C5122.5 (3)N2—C10—C13—C1420.9 (4)
C7—N1—C6—C570.1 (4)O1—C13—C14—C1539.9 (4)
C9—N1—C7—C817.1 (5)C10—C13—C14—C15140.5 (3)
C6—N1—C7—C8174.0 (3)O1—C13—C14—C19132.9 (3)
N1—C7—C8—S125.5 (4)C10—C13—C14—C1946.7 (4)
C9—S1—C8—C722.4 (3)C19—C14—C15—C161.1 (5)
C6—N1—C9—C1014.9 (5)C13—C14—C15—C16174.2 (3)
C7—N1—C9—C10177.5 (3)C14—C15—C16—C171.6 (5)
C6—N1—C9—S1167.3 (2)C15—C16—C17—F1178.9 (3)
C7—N1—C9—S10.3 (4)C15—C16—C17—C180.9 (5)
C8—S1—C9—N113.5 (3)F1—C17—C18—C19180.0 (3)
C8—S1—C9—C10164.5 (3)C16—C17—C18—C190.2 (5)
N1—C9—C10—N20.1 (5)C17—C18—C19—C140.7 (5)
S1—C9—C10—N2177.5 (2)C15—C14—C19—C180.0 (5)
N1—C9—C10—C13179.3 (3)C13—C14—C19—C18172.8 (3)
S1—C9—C10—C133.1 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2A···N4i0.932.613.519 (6)168
C4—H4B···F1ii0.932.533.317 (5)143
C11—H11A···O1iii0.932.383.279 (7)164
Symmetry codes: (i) x+1, y+2, z; (ii) x1, y, z1; (iii) x+1, y+2, z+1.
 

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