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In the title compound, C15H12FN3O, an intra­molecular C—H...F hydrogen bond forms a six-membered ring. Mol­ecules are linked into a tape along the b axis by an inter­molecular C—H...N hydrogen bond. The crystal packing is further stabilized by C—H...π and π–π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806046320/is2101sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806046320/is2101Isup2.hkl
Contains datablock I

CCDC reference: 630026

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.043
  • wR factor = 0.143
  • Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for N2 - N3 .. 8.46 su
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

3-(1H-Benzotriazol-1-yl)-1-(2-fluorophenyl)propan-1-one top
Crystal data top
C15H12FN3OF(000) = 560
Mr = 269.28Dx = 1.398 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 15.551 (6) ÅCell parameters from 2022 reflections
b = 5.971 (2) Åθ = 9.3–24.9°
c = 14.221 (6) ŵ = 0.10 mm1
β = 104.339 (6)°T = 293 K
V = 1279.4 (8) Å3Column, colourless
Z = 40.47 × 0.17 × 0.09 mm
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer
2520 independent reflections
Radiation source: fine-focus sealed tube1923 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
Detector resolution: 8.33 pixels mm-1θmax = 26.1°, θmin = 2.7°
ω scansh = 1916
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 76
Tmin = 0.954, Tmax = 0.991l = 1717
6710 measured reflections
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143H-atom parameters constrained
S = 0.97 w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
2520 reflections(Δ/σ)max = 0.001
181 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.19 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
F10.73132 (8)0.0299 (2)0.82666 (8)0.0783 (4)
C141.07969 (11)0.3440 (3)1.17473 (11)0.0476 (4)
H14A1.11980.23281.20260.057*
N10.84451 (9)0.5051 (2)1.09814 (10)0.0465 (4)
C80.74309 (10)0.2240 (3)1.00551 (10)0.0415 (4)
H8A0.72360.33280.95400.050*
H8B0.79250.14140.99220.050*
N20.82312 (10)0.7122 (3)1.06016 (11)0.0594 (4)
C100.93446 (10)0.4781 (2)1.12024 (9)0.0391 (4)
N30.89552 (10)0.8195 (2)1.05724 (11)0.0553 (4)
C150.99127 (11)0.3037 (3)1.16131 (10)0.0431 (4)
H15A0.97000.16811.17850.052*
C121.05736 (11)0.7183 (3)1.10718 (11)0.0473 (4)
H12A1.07900.85251.08910.057*
O10.63199 (9)0.0660 (3)1.07216 (10)0.0762 (5)
C110.96620 (11)0.6808 (2)1.09384 (10)0.0422 (4)
C70.66832 (10)0.0648 (3)1.00583 (12)0.0473 (4)
C60.63805 (10)0.1001 (3)0.92444 (11)0.0459 (4)
C50.67040 (11)0.1186 (3)0.84222 (12)0.0516 (4)
C90.77424 (11)0.3463 (3)1.10168 (12)0.0532 (5)
H9A0.72460.42551.11630.064*
H9B0.79600.23851.15310.064*
C131.11281 (11)0.5484 (3)1.14793 (11)0.0484 (4)
H13A1.17380.56761.15830.058*
C10.57469 (11)0.2587 (3)0.93320 (14)0.0610 (5)
H1A0.55050.25320.98680.073*
C40.64411 (13)0.2827 (3)0.77343 (14)0.0631 (5)
H4A0.66810.28930.71980.076*
C30.58224 (13)0.4361 (4)0.78476 (15)0.0708 (6)
H3B0.56400.54860.73890.085*
C20.54705 (13)0.4230 (4)0.86449 (16)0.0748 (6)
H2B0.50430.52600.87190.090*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0938 (9)0.0897 (9)0.0622 (7)0.0365 (7)0.0398 (7)0.0199 (6)
C140.0549 (10)0.0464 (10)0.0414 (9)0.0106 (7)0.0118 (7)0.0029 (7)
N10.0489 (8)0.0441 (8)0.0438 (7)0.0000 (6)0.0062 (6)0.0044 (6)
C80.0418 (9)0.0432 (9)0.0400 (8)0.0029 (7)0.0111 (6)0.0017 (6)
N20.0608 (10)0.0499 (9)0.0610 (9)0.0133 (7)0.0025 (7)0.0008 (7)
C100.0492 (9)0.0380 (9)0.0292 (7)0.0009 (7)0.0082 (6)0.0068 (6)
N30.0607 (10)0.0417 (9)0.0591 (9)0.0062 (7)0.0068 (7)0.0016 (6)
C150.0586 (10)0.0347 (8)0.0360 (8)0.0018 (7)0.0119 (7)0.0001 (6)
C120.0612 (11)0.0408 (9)0.0423 (9)0.0071 (8)0.0173 (7)0.0022 (6)
O10.0708 (9)0.1059 (12)0.0634 (9)0.0246 (8)0.0385 (7)0.0178 (8)
C110.0567 (10)0.0350 (8)0.0333 (7)0.0019 (7)0.0082 (7)0.0024 (6)
C70.0403 (9)0.0574 (11)0.0448 (9)0.0019 (7)0.0117 (7)0.0032 (7)
C60.0383 (8)0.0490 (10)0.0474 (9)0.0001 (7)0.0047 (7)0.0043 (7)
C50.0507 (10)0.0533 (10)0.0496 (9)0.0058 (8)0.0100 (7)0.0015 (8)
C90.0494 (10)0.0659 (12)0.0451 (9)0.0060 (8)0.0134 (7)0.0067 (8)
C130.0493 (9)0.0554 (10)0.0430 (9)0.0001 (8)0.0163 (7)0.0029 (7)
C10.0480 (10)0.0696 (12)0.0627 (11)0.0102 (9)0.0082 (8)0.0077 (9)
C40.0666 (12)0.0625 (12)0.0558 (11)0.0003 (10)0.0069 (9)0.0109 (9)
C30.0715 (14)0.0585 (12)0.0695 (13)0.0058 (10)0.0073 (10)0.0102 (9)
C20.0641 (13)0.0655 (14)0.0849 (16)0.0216 (10)0.0003 (11)0.0047 (11)
Geometric parameters (Å, º) top
F1—C51.355 (2)C12—C111.401 (2)
C14—C151.362 (2)C12—H12A0.9300
C14—C131.413 (2)O1—C71.214 (2)
C14—H14A0.9300C7—C61.503 (2)
N1—N21.357 (2)C6—C51.387 (2)
N1—C101.365 (2)C6—C11.394 (2)
N1—C91.457 (2)C5—C41.373 (3)
C8—C71.503 (2)C9—H9A0.9700
C8—C91.520 (2)C9—H9B0.9700
C8—H8A0.9700C13—H13A0.9300
C8—H8B0.9700C1—C21.377 (3)
N2—N31.305 (2)C1—H1A0.9300
C10—C111.393 (2)C4—C31.367 (3)
C10—C151.397 (2)C4—H4A0.9300
N3—C111.372 (2)C3—C21.378 (3)
C15—H15A0.9300C3—H3B0.9300
C12—C131.364 (2)C2—H2B0.9300
C15—C14—C13122.51 (15)C8—C7—C6120.46 (13)
C15—C14—H14A118.7C5—C6—C1115.68 (16)
C13—C14—H14A118.7C5—C6—C7126.25 (15)
N2—N1—C10109.59 (14)C1—C6—C7117.98 (15)
N2—N1—C9119.65 (14)F1—C5—C4116.57 (16)
C10—N1—C9130.50 (14)F1—C5—C6119.99 (15)
C7—C8—C9112.06 (13)C4—C5—C6123.44 (17)
C7—C8—H8A109.2N1—C9—C8110.86 (13)
C9—C8—H8A109.2N1—C9—H9A109.5
C7—C8—H8B109.2C8—C9—H9A109.5
C9—C8—H8B109.2N1—C9—H9B109.5
H8A—C8—H8B107.9C8—C9—H9B109.5
N3—N2—N1109.36 (14)H9A—C9—H9B108.1
N1—C10—C11104.27 (14)C12—C13—C14121.50 (16)
N1—C10—C15133.66 (15)C12—C13—H13A119.3
C11—C10—C15122.06 (15)C14—C13—H13A119.3
N2—N3—C11107.96 (14)C2—C1—C6121.61 (18)
C14—C15—C10116.04 (14)C2—C1—H1A119.2
C14—C15—H15A122.0C6—C1—H1A119.2
C10—C15—H15A122.0C3—C4—C5119.24 (19)
C13—C12—C11116.79 (15)C3—C4—H4A120.4
C13—C12—H12A121.6C5—C4—H4A120.4
C11—C12—H12A121.6C4—C3—C2119.59 (19)
N3—C11—C10108.82 (15)C4—C3—H3B120.2
N3—C11—C12130.09 (15)C2—C3—H3B120.2
C10—C11—C12121.09 (14)C1—C2—C3120.44 (19)
O1—C7—C8120.52 (15)C1—C2—H2B119.8
O1—C7—C6119.02 (15)C3—C2—H2B119.8
C10—N1—N2—N30.20 (18)O1—C7—C6—C5177.82 (17)
C9—N1—N2—N3175.08 (13)C8—C7—C6—C52.8 (3)
N2—N1—C10—C110.23 (16)O1—C7—C6—C15.7 (2)
C9—N1—C10—C11174.38 (15)C8—C7—C6—C1173.64 (15)
N2—N1—C10—C15178.92 (15)C1—C6—C5—F1179.10 (15)
C9—N1—C10—C156.9 (3)C7—C6—C5—F14.4 (3)
N1—N2—N3—C110.08 (18)C1—C6—C5—C41.0 (3)
C13—C14—C15—C100.7 (2)C7—C6—C5—C4175.50 (16)
N1—C10—C15—C14178.02 (15)N2—N1—C9—C883.72 (18)
C11—C10—C15—C140.5 (2)C10—N1—C9—C889.93 (19)
N2—N3—C11—C100.07 (17)C7—C8—C9—N1177.98 (13)
N2—N3—C11—C12179.16 (15)C11—C12—C13—C140.4 (2)
N1—C10—C11—N30.18 (16)C15—C14—C13—C120.3 (2)
C15—C10—C11—N3179.06 (13)C5—C6—C1—C20.4 (3)
N1—C10—C11—C12179.13 (13)C7—C6—C1—C2176.39 (17)
C15—C10—C11—C120.2 (2)F1—C5—C4—C3179.45 (17)
C13—C12—C11—N3178.45 (15)C6—C5—C4—C30.7 (3)
C13—C12—C11—C100.7 (2)C5—C4—C3—C20.3 (3)
C9—C8—C7—O19.6 (2)C6—C1—C2—C30.5 (3)
C9—C8—C7—C6169.74 (14)C4—C3—C2—C10.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8B···F10.972.402.760 (2)101
C8—H8B···N3i0.972.533.336 (3)140
C15—H15A···Cg3ii0.932.803.446 (2)127
Symmetry codes: (i) x, y1, z; (ii) x+2, y1/2, z+5/2.
 

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