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The asymmetric unit of the title compound, C15H11F1N2, comprises two mol­ecules with dihedral angles of 50.6 (1)/49.2 (1) and 51.5 (1)/53.3 (1)° between the pyrazole and, respectively, the phenyl and 4-fluoro­phenyl rings. One intermolecular C—H...F close contact is noted for each unique mol­ecule.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802009911/na6165sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802009911/na6165Isup2.hkl
Contains datablock I

CCDC reference: 189891

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.082
  • wR factor = 0.238
  • Data-to-parameter ratio = 16.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON97 (Spek, 1997); software used to prepare material for publication: SHELXL97.

5-(4-Fluorophenyl)-1-phenylpyrazole top
Crystal data top
C15H11FN2Z = 4
Mr = 238.26F(000) = 496
Triclinic, P1Dx = 1.329 Mg m3
a = 7.847 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.904 (2) ÅCell parameters from 16018 reflections
c = 19.551 (4) Åθ = 2.9–27.5°
α = 90.20 (3)°µ = 0.09 mm1
β = 100.92 (3)°T = 150 K
γ = 90.61 (3)°Block, yellow
V = 1190.5 (4) Å30.20 × 0.18 × 0.10 mm
Data collection top
Bruker–Nonius KappaCCD area-detector
diffractometer
5311 independent reflections
Radiation source: Bruker–Nonius FR591 rotating anode3979 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.065
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.0°
φ and ω scansh = 1010
Absorption correction: multi-scan
SORTAV (Blessing, 1995)
k = 1010
Tmin = 0.982, Tmax = 0.991l = 2325
17989 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.082H-atom parameters constrained
wR(F2) = 0.238 w = 1/[σ2(Fo2) + (0.0756P)2 + 2.8942P]
where P = (Fo2 + 2Fc2)/3
S = 1.17(Δ/σ)max < 0.001
5311 reflectionsΔρmax = 0.32 e Å3
326 parametersΔρmin = 0.33 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.077 (9)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N1A0.4367 (4)0.1330 (4)0.36661 (15)0.0218 (6)
N2A0.5261 (4)0.2825 (4)0.37098 (15)0.0254 (7)
C3A0.3603 (5)0.2688 (5)0.45435 (18)0.0256 (7)
H3A0.30920.30050.49280.032*
C4A0.4788 (5)0.3629 (5)0.42401 (19)0.0271 (8)
H4A0.52070.47220.43970.034*
C5A0.3341 (4)0.1209 (4)0.41656 (17)0.0223 (7)
C6A0.4649 (4)0.0060 (4)0.31756 (18)0.0232 (7)
C7A0.5048 (4)0.1569 (5)0.33972 (19)0.0256 (8)
H7A0.51440.18540.38750.032*
C8A0.5306 (5)0.2786 (5)0.2915 (2)0.0270 (8)
H8A0.55800.39110.30630.034*
C9A0.5167 (5)0.2375 (5)0.2222 (2)0.0290 (8)
H9A0.53380.32140.18930.036*
C10A0.4774 (5)0.0718 (5)0.2005 (2)0.0293 (8)
H10A0.46810.04330.15280.037*
C11A0.4517 (5)0.0517 (5)0.24812 (18)0.0255 (8)
H11A0.42570.16460.23360.032*
C12A0.2110 (4)0.0204 (4)0.41833 (18)0.0225 (7)
C13A0.2022 (5)0.0992 (5)0.48138 (19)0.0263 (8)
H13A0.27640.06240.52300.033*
C14A0.0851 (5)0.2314 (5)0.4834 (2)0.0284 (8)
H14A0.07830.28620.52600.035*
C15A0.0201 (5)0.2804 (5)0.4225 (2)0.0281 (8)
F15A0.1352 (3)0.4114 (3)0.42401 (13)0.0363 (6)
C16A0.0170 (5)0.2055 (5)0.3591 (2)0.0281 (8)
H16A0.09240.24270.31770.035*
C17A0.1002 (5)0.0743 (5)0.35808 (19)0.0255 (7)
H17A0.10500.01970.31520.032*
N1B0.1848 (4)0.4929 (4)0.13510 (15)0.0216 (6)
N2B0.3247 (4)0.3953 (4)0.13030 (16)0.0249 (7)
C3B0.3901 (5)0.4668 (5)0.07906 (19)0.0274 (8)
H3B0.48980.42650.06340.034*
C4B0.2963 (5)0.6070 (5)0.05110 (19)0.0260 (8)
H4B0.31840.67720.01430.032*
C5B0.1646 (4)0.6222 (4)0.08822 (18)0.0230 (7)
C6B0.0749 (4)0.4461 (4)0.18318 (18)0.0220 (7)
C7B0.1017 (5)0.4289 (4)0.15942 (19)0.0244 (7)
H7B0.15070.44870.11190.031*
C8B0.2074 (5)0.3820 (5)0.2066 (2)0.0268 (8)
H8B0.32910.36980.19090.034*
C9B0.1363 (5)0.3533 (5)0.2755 (2)0.0274 (8)
H9B0.20820.32040.30730.034*
C10B0.0423 (5)0.3730 (5)0.29814 (19)0.0280 (8)
H10B0.09180.35490.34570.035*
C11B0.1481 (5)0.4185 (4)0.25210 (19)0.0247 (7)
H11B0.26990.43080.26770.031*
C12B0.0282 (4)0.7509 (4)0.08464 (18)0.0225 (7)
C13B0.0794 (5)0.7846 (5)0.02086 (19)0.0266 (8)
H13B0.06430.72450.01970.033*
C14B0.2085 (5)0.9054 (5)0.0162 (2)0.0284 (8)
H14B0.28240.92880.02700.036*
C15B0.2260 (5)0.9902 (4)0.0760 (2)0.0274 (8)
F15B0.3533 (3)1.1080 (3)0.07171 (12)0.0354 (6)
C16B0.1208 (5)0.9627 (5)0.1395 (2)0.0298 (8)
H16B0.13521.02520.17960.037*
C17B0.0069 (5)0.8412 (5)0.14350 (19)0.0268 (8)
H17B0.08070.81950.18690.033*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0228 (14)0.0216 (14)0.0217 (15)0.0047 (11)0.0063 (11)0.0007 (11)
N2A0.0278 (15)0.0238 (15)0.0243 (16)0.0066 (12)0.0048 (12)0.0006 (11)
C3A0.0272 (18)0.0289 (18)0.0206 (17)0.0029 (14)0.0042 (14)0.0009 (13)
C4A0.0313 (19)0.0239 (18)0.0253 (19)0.0051 (14)0.0039 (15)0.0034 (14)
C5A0.0199 (16)0.0282 (18)0.0186 (17)0.0010 (13)0.0032 (13)0.0033 (13)
C6A0.0188 (16)0.0280 (18)0.0231 (18)0.0015 (13)0.0050 (13)0.0020 (13)
C7A0.0224 (17)0.0298 (19)0.0244 (18)0.0010 (14)0.0039 (14)0.0014 (14)
C8A0.0230 (17)0.0240 (18)0.034 (2)0.0017 (14)0.0054 (15)0.0006 (14)
C9A0.0250 (18)0.033 (2)0.030 (2)0.0027 (15)0.0089 (15)0.0072 (15)
C10A0.0276 (18)0.037 (2)0.0241 (19)0.0007 (15)0.0076 (15)0.0007 (15)
C11A0.0253 (17)0.0272 (18)0.0249 (18)0.0008 (14)0.0069 (14)0.0025 (14)
C12A0.0203 (16)0.0223 (17)0.0255 (18)0.0006 (13)0.0063 (13)0.0007 (13)
C13A0.0255 (17)0.0293 (19)0.0246 (19)0.0002 (14)0.0058 (14)0.0032 (14)
C14A0.0316 (19)0.0274 (18)0.0283 (19)0.0003 (15)0.0108 (15)0.0053 (14)
C15A0.0246 (17)0.0224 (17)0.040 (2)0.0051 (14)0.0143 (16)0.0009 (15)
F15A0.0356 (12)0.0306 (12)0.0458 (14)0.0125 (10)0.0164 (10)0.0015 (10)
C16A0.0249 (18)0.032 (2)0.0273 (19)0.0045 (15)0.0045 (14)0.0036 (15)
C17A0.0257 (17)0.0281 (18)0.0231 (18)0.0022 (14)0.0058 (14)0.0015 (14)
N1B0.0195 (13)0.0249 (15)0.0213 (15)0.0031 (11)0.0055 (11)0.0012 (11)
N2B0.0217 (14)0.0288 (16)0.0248 (16)0.0046 (12)0.0053 (12)0.0017 (12)
C3B0.0235 (17)0.034 (2)0.0257 (19)0.0044 (14)0.0068 (14)0.0029 (14)
C4B0.0259 (17)0.0300 (19)0.0235 (18)0.0015 (14)0.0084 (14)0.0002 (14)
C5B0.0230 (17)0.0250 (17)0.0208 (17)0.0009 (13)0.0033 (13)0.0014 (13)
C6B0.0245 (17)0.0182 (16)0.0245 (18)0.0009 (13)0.0073 (13)0.0003 (12)
C7B0.0234 (17)0.0265 (18)0.0231 (18)0.0016 (14)0.0033 (14)0.0008 (13)
C8B0.0199 (16)0.0279 (18)0.033 (2)0.0005 (14)0.0062 (14)0.0004 (14)
C9B0.0289 (18)0.0251 (18)0.031 (2)0.0033 (14)0.0131 (15)0.0019 (14)
C10B0.0319 (19)0.0300 (19)0.0222 (18)0.0028 (15)0.0056 (15)0.0035 (14)
C11B0.0203 (16)0.0269 (18)0.0266 (19)0.0013 (13)0.0035 (13)0.0001 (14)
C12B0.0219 (16)0.0215 (17)0.0252 (18)0.0000 (13)0.0074 (13)0.0007 (13)
C13B0.0256 (18)0.0275 (18)0.0267 (19)0.0005 (14)0.0046 (14)0.0012 (14)
C14B0.0262 (18)0.0293 (19)0.028 (2)0.0022 (15)0.0009 (15)0.0052 (14)
C15B0.0236 (17)0.0234 (18)0.037 (2)0.0058 (14)0.0089 (15)0.0071 (15)
F15B0.0318 (12)0.0332 (12)0.0435 (14)0.0116 (9)0.0126 (10)0.0095 (10)
C16B0.034 (2)0.0287 (19)0.028 (2)0.0053 (15)0.0110 (16)0.0006 (15)
C17B0.0262 (18)0.0283 (18)0.0255 (19)0.0029 (14)0.0038 (14)0.0015 (14)
Geometric parameters (Å, º) top
N1A—N2A1.362 (4)N1B—C5B1.366 (4)
N1A—C5A1.381 (4)N1B—N2B1.366 (4)
N1A—C6A1.433 (4)N1B—C6B1.437 (4)
N2A—C4A1.328 (5)N2B—C3B1.334 (5)
C3A—C5A1.373 (5)C3B—C4B1.392 (5)
C3A—C4A1.403 (5)C3B—H3B0.95
C3A—H3A0.95C4B—C5B1.377 (5)
C4A—H4A0.95C4B—H4B0.95
C5A—C12A1.474 (5)C5B—C12B1.477 (5)
C6A—C7A1.380 (5)C6B—C11B1.380 (5)
C6A—C11A1.391 (5)C6B—C7B1.381 (5)
C7A—C8A1.387 (5)C7B—C8B1.400 (5)
C7A—H7A0.95C7B—H7B0.95
C8A—C9A1.380 (5)C8B—C9B1.378 (5)
C8A—H8A0.95C8B—H8B0.95
C9A—C10A1.397 (6)C9B—C10B1.394 (5)
C9A—H9A0.9500C9B—H9B0.95
C10A—C11A1.389 (5)C10B—C11B1.382 (5)
C10A—H10A0.95C10B—H10B0.95
C11A—H11A0.95C11B—H11B0.95
C12A—C17A1.388 (5)C12B—C17B1.390 (5)
C12A—C13A1.396 (5)C12B—C13B1.395 (5)
C13A—C14A1.390 (5)C13B—C14B1.390 (5)
C13A—H13A0.95C13B—H13B0.95
C14A—C15A1.366 (6)C14B—C15B1.375 (6)
C14A—H14A0.95C14B—H14B0.95
C15A—F15A1.371 (4)C15B—F15B1.364 (4)
C15A—C16A1.381 (5)C15B—C16B1.375 (5)
C16A—C17A1.381 (5)C16B—C17B1.387 (5)
C16A—H16A0.95C16B—H16B0.95
C17A—H17A0.95C17B—H17B0.95
N2A—N1A—C5A112.0 (3)C5B—N1B—N2B112.2 (3)
N2A—N1A—C6A120.1 (3)C5B—N1B—C6B128.4 (3)
C5A—N1A—C6A127.7 (3)N2B—N1B—C6B119.3 (3)
C4A—N2A—N1A104.2 (3)C3B—N2B—N1B103.8 (3)
C5A—C3A—C4A105.1 (3)N2B—C3B—C4B112.6 (3)
C5A—C3A—H3A127.4N2B—C3B—H3B123.7
C4A—C3A—H3A127.4C4B—C3B—H3B123.7
N2A—C4A—C3A112.6 (3)C5B—C4B—C3B105.2 (3)
N2A—C4A—H4A123.7C5B—C4B—H4B127.4
C3A—C4A—H4A123.7C3B—C4B—H4B127.4
C3A—C5A—N1A106.1 (3)N1B—C5B—C4B106.3 (3)
C3A—C5A—C12A131.0 (3)N1B—C5B—C12B123.1 (3)
N1A—C5A—C12A122.5 (3)C4B—C5B—C12B130.5 (3)
C7A—C6A—C11A121.6 (3)C11B—C6B—C7B121.3 (3)
C7A—C6A—N1A120.0 (3)C11B—C6B—N1B119.4 (3)
C11A—C6A—N1A118.4 (3)C7B—C6B—N1B119.3 (3)
C6A—C7A—C8A119.3 (3)C6B—C7B—C8B118.9 (3)
C6A—C7A—H7A120.4C6B—C7B—H7B120.6
C8A—C7A—H7A120.4C8B—C7B—H7B120.6
C9A—C8A—C7A120.5 (3)C9B—C8B—C7B120.6 (3)
C9A—C8A—H8A119.8C9B—C8B—H8B119.7
C7A—C8A—H8A119.8C7B—C8B—H8B119.7
C8A—C9A—C10A119.7 (3)C8B—C9B—C10B119.3 (3)
C8A—C9A—H9A120.2C8B—C9B—H9B120.4
C10A—C9A—H9A120.2C10B—C9B—H9B120.4
C11A—C10A—C9A120.6 (3)C11B—C10B—C9B120.8 (3)
C11A—C10A—H10A119.7C11B—C10B—H10B119.6
C9A—C10A—H10A119.7C9B—C10B—H10B119.6
C10A—C11A—C6A118.4 (3)C6B—C11B—C10B119.2 (3)
C10A—C11A—H11A120.8C6B—C11B—H11B120.4
C6A—C11A—H11A120.8C10B—C11B—H11B120.4
C17A—C12A—C13A119.2 (3)C17B—C12B—C13B119.4 (3)
C17A—C12A—C5A120.7 (3)C17B—C12B—C5B121.1 (3)
C13A—C12A—C5A120.0 (3)C13B—C12B—C5B119.5 (3)
C14A—C13A—C12A120.2 (3)C14B—C13B—C12B120.5 (3)
C14A—C13A—H13A119.9C14B—C13B—H13B119.7
C12A—C13A—H13A119.9C12B—C13B—H13B119.7
C15A—C14A—C13A118.2 (3)C15B—C14B—C13B118.1 (3)
C15A—C14A—H14A120.9C15B—C14B—H14B121.0
C13A—C14A—H14A120.9C13B—C14B—H14B121.0
C14A—C15A—F15A118.6 (3)F15B—C15B—C16B118.6 (3)
C14A—C15A—C16A123.7 (3)F15B—C15B—C14B118.2 (3)
F15A—C15A—C16A117.8 (3)C16B—C15B—C14B123.2 (3)
C15A—C16A—C17A117.3 (3)C15B—C16B—C17B118.1 (3)
C15A—C16A—H16A121.4C15B—C16B—H16B120.9
C17A—C16A—H16A121.4C17B—C16B—H16B120.9
C16A—C17A—C12A121.4 (3)C16B—C17B—C12B120.7 (3)
C16A—C17A—H17A119.3C16B—C17B—H17B119.6
C12A—C17A—H17A119.3C12B—C17B—H17B119.6
C5A—N1A—N2A—C4A0.1 (4)C5B—N1B—N2B—C3B0.3 (4)
C6A—N1A—N2A—C4A175.5 (3)C6B—N1B—N2B—C3B176.3 (3)
N1A—N2A—C4A—C3A0.0 (4)N1B—N2B—C3B—C4B0.1 (4)
C5A—C3A—C4A—N2A0.2 (4)N2B—C3B—C4B—C5B0.2 (4)
C4A—C3A—C5A—N1A0.3 (4)N2B—N1B—C5B—C4B0.5 (4)
C4A—C3A—C5A—C12A172.8 (4)C6B—N1B—C5B—C4B175.8 (3)
N2A—N1A—C5A—C3A0.3 (4)N2B—N1B—C5B—C12B177.1 (3)
C6A—N1A—C5A—C3A175.0 (3)C6B—N1B—C5B—C12B6.6 (5)
N2A—N1A—C5A—C12A173.5 (3)C3B—C4B—C5B—N1B0.4 (4)
C6A—N1A—C5A—C12A11.2 (5)C3B—C4B—C5B—C12B176.9 (4)
N2A—N1A—C6A—C7A127.2 (3)C5B—N1B—C6B—C11B131.1 (4)
C5A—N1A—C6A—C7A47.7 (5)N2B—N1B—C6B—C11B52.9 (4)
N2A—N1A—C6A—C11A52.6 (4)C5B—N1B—C6B—C7B49.1 (5)
C5A—N1A—C6A—C11A132.6 (4)N2B—N1B—C6B—C7B126.9 (3)
C11A—C6A—C7A—C8A0.7 (5)C11B—C6B—C7B—C8B0.3 (5)
N1A—C6A—C7A—C8A179.6 (3)N1B—C6B—C7B—C8B179.5 (3)
C6A—C7A—C8A—C9A0.0 (5)C6B—C7B—C8B—C9B0.0 (5)
C7A—C8A—C9A—C10A0.4 (5)C7B—C8B—C9B—C10B0.6 (5)
C8A—C9A—C10A—C11A0.2 (5)C8B—C9B—C10B—C11B0.9 (6)
C9A—C10A—C11A—C6A0.4 (5)C7B—C6B—C11B—C10B0.0 (5)
C7A—C6A—C11A—C10A0.8 (5)N1B—C6B—C11B—C10B179.8 (3)
N1A—C6A—C11A—C10A179.4 (3)C9B—C10B—C11B—C6B0.6 (6)
C3A—C5A—C12A—C17A125.8 (4)N1B—C5B—C12B—C17B52.5 (5)
N1A—C5A—C12A—C17A46.3 (5)C4B—C5B—C12B—C17B124.5 (4)
C3A—C5A—C12A—C13A52.7 (5)N1B—C5B—C12B—C13B128.6 (4)
N1A—C5A—C12A—C13A135.2 (4)C4B—C5B—C12B—C13B54.4 (5)
C17A—C12A—C13A—C14A0.8 (5)C17B—C12B—C13B—C14B1.0 (5)
C5A—C12A—C13A—C14A179.3 (3)C5B—C12B—C13B—C14B179.9 (3)
C12A—C13A—C14A—C15A0.3 (5)C12B—C13B—C14B—C15B0.2 (5)
C13A—C14A—C15A—F15A179.6 (3)C13B—C14B—C15B—F15B179.5 (3)
C13A—C14A—C15A—C16A0.2 (6)C13B—C14B—C15B—C16B0.9 (6)
C14A—C15A—C16A—C17A0.2 (6)F15B—C15B—C16B—C17B179.2 (3)
F15A—C15A—C16A—C17A179.6 (3)C14B—C15B—C16B—C17B1.2 (6)
C15A—C16A—C17A—C12A0.4 (5)C15B—C16B—C17B—C12B0.4 (6)
C13A—C12A—C17A—C16A0.9 (5)C13B—C12B—C17B—C16B0.7 (5)
C5A—C12A—C17A—C16A179.4 (3)C5B—C12B—C17B—C16B179.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3A—H3A···F15Ai0.952.483.415 (4)169
C4B—H4B···F15Bii0.952.443.385 (4)171
Symmetry codes: (i) x, y, z+1; (ii) x, y+2, z.
 

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