Literature DB >> 22219945

(2,4-Difluoro-phen-yl)[1-(1H-1,2,4-triazol-1-yl)cyclo-prop-yl]methanone.

Chunli Wu1, Wei Lei, Huiyan Ma, Jiabin Qiao, Aixing Li.   

Abstract

The asymmetric unit of the title compound, C(12)H(9)F(2)N(3)O, contains two independent mol-ecules (A and B) in which the benzene and cyclo-propane rings form dihedral angles of 33.0 (1) and 29.7 (1)°, respectively. In the crystal, weak inter-molecular C-H⋯O hydrogen bonds link alternating A and B mol-ecules into chains along [010].

Entities:  

Year:  2011        PMID: 22219945      PMCID: PMC3247327          DOI: 10.1107/S1600536811040037

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN: 1600-5368


Related literature

For applications of triazole derivatives, see: Che & Zhang (2009 ▶); Lieven & Leo (2005 ▶). For related structures, see: Tarun et al. (1998 ▶).

Experimental

Crystal data

C12H9F2N3O M = 249.22 Triclinic, a = 9.6067 (11) Å b = 11.4840 (13) Å c = 11.9127 (14) Å α = 73.652 (1)° β = 84.202 (2)° γ = 69.260 (1)° V = 1179.4 (2) Å3 Z = 4 Mo Kα radiation μ = 0.12 mm−1 T = 298 K 0.49 × 0.40 × 0.38 mm

Data collection

Rigaku R-AXIS CCD detector diffractometer Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.983, T max = 0.986 5900 measured reflections 4080 independent reflections 2816 reflections with I > 2σ(I) R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.038 wR(F 2) = 0.111 S = 1.02 4080 reflections 326 parameters H-atom parameters constrained Δρmax = 0.14 e Å−3 Δρmin = −0.16 e Å−3 Data collection: R-AXIS II Software (Rigaku, 1997 ▶); cell refinement: R-AXIS II Software; data reduction: R-AXIS II Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: TEXSAN (Molecular Structure Corporation, 1992 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811040037/cv5156sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811040037/cv5156Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811040037/cv5156Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C12H9F2N3OF(000) = 512
Mr = 249.22Dx = 1.404 Mg m3
Triclinic, P1Melting point: 362.15 K
a = 9.6067 (11) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.4840 (13) ÅCell parameters from 2449 reflections
c = 11.9127 (14) Åθ = 4.9–52.5°
α = 73.652 (1)°µ = 0.12 mm1
β = 84.202 (2)°T = 298 K
γ = 69.260 (1)°Block, colourless
V = 1179.4 (2) Å30.49 × 0.40 × 0.38 mm
Z = 4
Rigaku R-AXIS CCD detector diffractometer4080 independent reflections
Radiation source: fine-focus sealed tube2816 reflections with I > 2σ(I)
graphiteRint = 0.017
φ and ω scansθmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)h = −10→11
Tmin = 0.983, Tmax = 0.986k = −13→12
5900 measured reflectionsl = −13→14
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.111w = 1/[σ2(Fo2) + (0.0469P)2 + 0.2296P] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
4080 reflectionsΔρmax = 0.14 e Å3
326 parametersΔρmin = −0.16 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0200 (19)
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.
xyzUiso*/Ueq
F11.40947 (15)0.64219 (16)0.00685 (15)0.1017 (5)
F20.96387 (13)0.81942 (11)0.18986 (12)0.0717 (4)
F30.93617 (18)0.62666 (18)0.51796 (17)0.1195 (6)
F40.49568 (16)0.58407 (11)0.69708 (13)0.0857 (4)
C11.2783 (2)0.6334 (2)0.0552 (2)0.0647 (6)
C21.2443 (2)0.5265 (2)0.0588 (2)0.0668 (6)
H2A1.31020.45970.03020.080*
C31.1099 (2)0.52091 (19)0.10591 (18)0.0584 (5)
H3A1.08510.44850.11020.070*
C41.0094 (2)0.62149 (17)0.14757 (16)0.0478 (5)
C51.0544 (2)0.72398 (18)0.14347 (17)0.0512 (5)
C61.1876 (2)0.7330 (2)0.09827 (18)0.0591 (6)
H6A1.21510.80330.09690.071*
C70.8640 (2)0.61067 (19)0.19488 (18)0.0556 (5)
C80.7238 (2)0.72473 (17)0.16397 (16)0.0463 (5)
C90.5788 (2)0.7042 (2)0.1994 (2)0.0678 (6)
H9A0.49490.75410.14700.081*
H9B0.58170.61750.24030.081*
C100.6327 (3)0.7735 (2)0.26206 (19)0.0700 (6)
H10A0.66890.72910.34130.084*
H10B0.58200.86580.24800.084*
N20.7482 (2)0.78048 (16)−0.04611 (14)0.0591 (5)
N30.7144 (2)0.99200 (16)−0.08345 (15)0.0647 (5)
C130.8010 (3)0.6783 (3)0.5629 (2)0.0762 (7)
C140.7534 (3)0.8061 (2)0.5600 (2)0.0788 (7)
H14A0.81350.85580.52960.095*
C150.6152 (3)0.8589 (2)0.6032 (2)0.0691 (7)
H15A0.58210.94550.60300.083*
C160.5225 (2)0.78710 (18)0.64746 (18)0.0573 (6)
C170.5794 (3)0.65813 (19)0.64870 (19)0.0604 (6)
C180.7182 (3)0.6007 (2)0.6075 (2)0.0690 (6)
H18A0.75400.51340.61000.083*
C190.3729 (3)0.8500 (2)0.69230 (19)0.0678 (6)
C200.2382 (2)0.83360 (19)0.65607 (17)0.0582 (5)
C210.1380 (3)0.7875 (3)0.7494 (2)0.0928 (9)
H21A0.09000.73200.73420.111*
H21B0.16600.76840.83030.111*
C220.0889 (3)0.9228 (3)0.6814 (2)0.0884 (8)
H22A0.08640.98710.72040.106*
H22B0.01050.95070.62440.106*
N60.2577 (2)0.69776 (17)0.41577 (15)0.0633 (5)
N50.26550 (18)0.87964 (14)0.44550 (14)0.0533 (4)
C120.7074 (2)0.94269 (18)0.02927 (17)0.0536 (5)
H12A0.69070.98940.08460.064*
C110.7406 (3)0.8883 (2)−0.12474 (18)0.0662 (6)
H11A0.75250.8930−0.20420.079*
N10.72688 (16)0.81780 (13)0.05495 (12)0.0423 (4)
N40.25081 (17)0.79612 (14)0.54907 (13)0.0464 (4)
C240.2467 (2)0.68990 (19)0.52741 (19)0.0588 (5)
H24A0.23710.61900.58470.071*
C230.2694 (2)0.81488 (19)0.37037 (18)0.0542 (5)
H23A0.27970.84790.29040.065*
O10.85746 (19)0.50900 (16)0.25590 (17)0.0984 (6)
O20.3590 (2)0.9191 (2)0.75643 (18)0.1132 (7)
U11U22U33U12U13U23
F10.0625 (9)0.1236 (13)0.1359 (14)−0.0376 (9)0.0205 (9)−0.0597 (11)
F20.0660 (8)0.0637 (8)0.0980 (10)−0.0180 (6)−0.0012 (7)−0.0458 (7)
F30.0818 (12)0.1246 (14)0.1586 (17)−0.0256 (10)−0.0010 (10)−0.0595 (13)
F40.1023 (11)0.0479 (7)0.1065 (11)−0.0320 (7)−0.0159 (8)−0.0061 (7)
C10.0459 (12)0.0778 (16)0.0745 (15)−0.0183 (11)−0.0014 (10)−0.0297 (13)
C20.0566 (14)0.0630 (14)0.0824 (16)−0.0086 (11)−0.0069 (11)−0.0345 (12)
C30.0601 (13)0.0419 (11)0.0718 (14)−0.0118 (10)−0.0159 (11)−0.0146 (10)
C40.0504 (11)0.0401 (10)0.0495 (11)−0.0122 (9)−0.0116 (9)−0.0065 (8)
C50.0519 (12)0.0468 (11)0.0566 (12)−0.0101 (9)−0.0101 (9)−0.0215 (9)
C60.0542 (13)0.0580 (13)0.0741 (15)−0.0230 (10)−0.0108 (11)−0.0225 (11)
C70.0643 (13)0.0430 (12)0.0546 (12)−0.0207 (10)−0.0066 (10)−0.0001 (9)
C80.0522 (11)0.0431 (11)0.0444 (11)−0.0203 (9)−0.0006 (9)−0.0075 (8)
C90.0594 (13)0.0629 (14)0.0797 (16)−0.0295 (11)0.0040 (11)−0.0068 (12)
C100.0797 (16)0.0751 (15)0.0522 (13)−0.0272 (13)0.0119 (11)−0.0155 (11)
N20.0828 (13)0.0495 (10)0.0472 (10)−0.0189 (9)−0.0041 (8)−0.0197 (8)
N30.0933 (14)0.0466 (10)0.0496 (11)−0.0238 (9)−0.0031 (9)−0.0048 (8)
C130.0669 (16)0.0743 (17)0.0896 (18)−0.0180 (14)−0.0208 (13)−0.0258 (14)
C140.0871 (19)0.0678 (16)0.0901 (18)−0.0367 (15)−0.0249 (15)−0.0121 (14)
C150.0893 (18)0.0437 (12)0.0798 (16)−0.0221 (12)−0.0336 (14)−0.0140 (11)
C160.0774 (15)0.0406 (11)0.0577 (13)−0.0164 (10)−0.0262 (11)−0.0146 (9)
C170.0800 (16)0.0407 (11)0.0635 (14)−0.0227 (11)−0.0236 (11)−0.0075 (10)
C180.0771 (16)0.0447 (12)0.0835 (16)−0.0082 (12)−0.0308 (13)−0.0198 (11)
C190.0935 (18)0.0516 (13)0.0608 (14)−0.0151 (12)−0.0176 (12)−0.0253 (11)
C200.0743 (14)0.0527 (12)0.0469 (12)−0.0143 (11)−0.0016 (10)−0.0210 (10)
C210.117 (2)0.112 (2)0.0538 (15)−0.0430 (19)0.0201 (14)−0.0304 (15)
C220.0852 (18)0.094 (2)0.0825 (18)−0.0074 (15)0.0070 (14)−0.0493 (16)
N60.0885 (13)0.0544 (11)0.0570 (11)−0.0311 (10)0.0008 (9)−0.0215 (9)
N50.0702 (11)0.0415 (9)0.0490 (10)−0.0234 (8)0.0010 (8)−0.0078 (8)
C120.0735 (14)0.0383 (11)0.0507 (12)−0.0181 (10)−0.0012 (10)−0.0151 (9)
C110.0932 (17)0.0598 (14)0.0409 (12)−0.0215 (12)−0.0025 (11)−0.0111 (11)
N10.0511 (9)0.0361 (8)0.0403 (8)−0.0138 (7)−0.0024 (7)−0.0117 (7)
N40.0597 (10)0.0391 (8)0.0428 (9)−0.0187 (7)−0.0004 (7)−0.0121 (7)
C240.0857 (15)0.0456 (12)0.0534 (13)−0.0350 (11)0.0014 (10)−0.0105 (9)
C230.0663 (13)0.0528 (12)0.0447 (11)−0.0221 (10)0.0050 (9)−0.0140 (9)
O10.0834 (12)0.0565 (10)0.1217 (15)−0.0247 (9)−0.0031 (10)0.0301 (10)
O20.1266 (16)0.1143 (15)0.1246 (16)−0.0233 (12)−0.0190 (12)−0.0879 (14)
F1—C11.357 (3)C13—C141.365 (3)
F2—C51.354 (2)C14—C151.364 (3)
F3—C131.348 (3)C14—H14A0.9300
F4—C171.348 (2)C15—C161.390 (3)
C1—C61.366 (3)C15—H15A0.9300
C1—C21.366 (3)C16—C171.382 (3)
C2—C31.371 (3)C16—C191.483 (3)
C2—H2A0.9300C17—C181.371 (3)
C3—C41.396 (3)C18—H18A0.9300
C3—H3A0.9300C19—O21.215 (2)
C4—C51.378 (3)C19—C201.493 (3)
C4—C71.486 (3)C20—N41.437 (2)
C5—C61.364 (3)C20—C221.498 (3)
C6—H6A0.9300C20—C211.502 (3)
C7—O11.209 (2)C21—C221.464 (4)
C7—C81.498 (3)C21—H21A0.9700
C8—N11.436 (2)C21—H21B0.9700
C8—C91.494 (3)C22—H22A0.9700
C8—C101.503 (3)C22—H22B0.9700
C9—C101.470 (3)N6—C241.303 (3)
C9—H9A0.9700N6—C231.342 (3)
C9—H9B0.9700N5—C231.305 (2)
C10—H10A0.9700N5—N41.363 (2)
C10—H10B0.9700C12—N11.327 (2)
N2—C111.309 (3)C12—H12A0.9300
N2—N11.361 (2)C11—H11A0.9300
N3—C121.307 (2)N4—C241.330 (2)
N3—C111.348 (3)C24—H24A0.9300
C13—C181.364 (3)C23—H23A0.9300
F1—C1—C6117.4 (2)C17—C16—C15116.4 (2)
F1—C1—C2118.9 (2)C17—C16—C19124.0 (2)
C6—C1—C2123.7 (2)C15—C16—C19119.55 (19)
C1—C2—C3117.9 (2)F4—C17—C18118.42 (19)
C1—C2—H2A121.1F4—C17—C16117.9 (2)
C3—C2—H2A121.1C18—C17—C16123.6 (2)
C2—C3—C4121.47 (19)C13—C18—C17116.4 (2)
C2—C3—H3A119.3C13—C18—H18A121.8
C4—C3—H3A119.3C17—C18—H18A121.8
C5—C4—C3116.77 (19)O2—C19—C16119.7 (2)
C5—C4—C7124.50 (17)O2—C19—C20119.5 (2)
C3—C4—C7118.72 (17)C16—C19—C20120.83 (17)
F2—C5—C6117.88 (17)N4—C20—C19116.14 (18)
F2—C5—C4118.42 (18)N4—C20—C22116.23 (18)
C6—C5—C4123.66 (18)C19—C20—C22117.79 (19)
C5—C6—C1116.47 (19)N4—C20—C21117.26 (19)
C5—C6—H6A121.8C19—C20—C21118.64 (19)
C1—C6—H6A121.8C22—C20—C2158.42 (17)
O1—C7—C4120.29 (19)C22—C21—C2060.67 (17)
O1—C7—C8119.54 (19)C22—C21—H21A117.7
C4—C7—C8120.14 (16)C20—C21—H21A117.7
N1—C8—C9116.98 (16)C22—C21—H21B117.7
N1—C8—C7115.56 (15)C20—C21—H21B117.7
C9—C8—C7118.05 (17)H21A—C21—H21B114.8
N1—C8—C10117.75 (16)C21—C22—C2060.91 (16)
C9—C8—C1058.74 (14)C21—C22—H22A117.7
C7—C8—C10117.95 (17)C20—C22—H22A117.7
C10—C9—C860.96 (14)C21—C22—H22B117.7
C10—C9—H9A117.7C20—C22—H22B117.7
C8—C9—H9A117.7H22A—C22—H22B114.8
C10—C9—H9B117.7C24—N6—C23102.17 (16)
C8—C9—H9B117.7C23—N5—N4102.04 (15)
H9A—C9—H9B114.8N3—C12—N1111.64 (17)
C9—C10—C860.30 (14)N3—C12—H12A124.2
C9—C10—H10A117.7N1—C12—H12A124.2
C8—C10—H10A117.7N2—C11—N3115.84 (18)
C9—C10—H10B117.7N2—C11—H11A122.1
C8—C10—H10B117.7N3—C11—H11A122.1
H10A—C10—H10B114.9C12—N1—N2108.90 (15)
C11—N2—N1101.85 (15)C12—N1—C8132.04 (15)
C12—N3—C11101.76 (17)N2—N1—C8119.02 (14)
F3—C13—C18118.3 (2)C24—N4—N5108.55 (15)
F3—C13—C14118.2 (3)C24—N4—C20131.78 (17)
C18—C13—C14123.4 (3)N5—N4—C20119.64 (15)
C15—C14—C13118.1 (2)N6—C24—N4111.46 (18)
C15—C14—H14A120.9N6—C24—H24A124.3
C13—C14—H14A120.9N4—C24—H24A124.3
C14—C15—C16122.0 (2)N5—C23—N6115.78 (18)
C14—C15—H15A119.0N5—C23—H23A122.1
C16—C15—H15A119.0N6—C23—H23A122.1
F1—C1—C2—C3−178.8 (2)C17—C16—C19—O2132.8 (2)
C6—C1—C2—C31.6 (4)C15—C16—C19—O2−45.8 (3)
C1—C2—C3—C40.9 (3)C17—C16—C19—C20−49.5 (3)
C2—C3—C4—C5−2.6 (3)C15—C16—C19—C20131.9 (2)
C2—C3—C4—C7178.48 (19)O2—C19—C20—N4156.3 (2)
C3—C4—C5—F2−175.89 (17)C16—C19—C20—N4−21.4 (3)
C7—C4—C5—F22.9 (3)O2—C19—C20—C2211.7 (3)
C3—C4—C5—C62.1 (3)C16—C19—C20—C22−166.0 (2)
C7—C4—C5—C6−179.09 (19)O2—C19—C20—C21−55.6 (3)
F2—C5—C6—C1178.18 (18)C16—C19—C20—C21126.7 (2)
C4—C5—C6—C10.2 (3)N4—C20—C21—C22−105.5 (2)
F1—C1—C6—C5178.23 (19)C19—C20—C21—C22106.7 (2)
C2—C1—C6—C5−2.1 (3)N4—C20—C22—C21107.2 (2)
C5—C4—C7—O1−137.7 (2)C19—C20—C22—C21−108.2 (2)
C3—C4—C7—O141.0 (3)C11—N3—C12—N1−0.4 (2)
C5—C4—C7—C844.3 (3)N1—N2—C11—N3−0.8 (3)
C3—C4—C7—C8−136.94 (19)C12—N3—C11—N20.8 (3)
O1—C7—C8—N1−152.1 (2)N3—C12—N1—N2−0.1 (2)
C4—C7—C8—N125.9 (2)N3—C12—N1—C8−177.66 (18)
O1—C7—C8—C9−6.6 (3)C11—N2—N1—C120.5 (2)
C4—C7—C8—C9171.43 (17)C11—N2—N1—C8178.46 (17)
O1—C7—C8—C1060.9 (3)C9—C8—N1—C1293.1 (2)
C4—C7—C8—C10−121.1 (2)C7—C8—N1—C12−121.0 (2)
N1—C8—C9—C10−107.59 (19)C10—C8—N1—C1226.0 (3)
C7—C8—C9—C10107.3 (2)C9—C8—N1—N2−84.3 (2)
N1—C8—C10—C9106.28 (19)C7—C8—N1—N261.6 (2)
C7—C8—C10—C9−107.5 (2)C10—C8—N1—N2−151.36 (17)
F3—C13—C14—C15178.6 (2)C23—N5—N4—C24−0.2 (2)
C18—C13—C14—C15−0.7 (4)C23—N5—N4—C20−178.35 (17)
C13—C14—C15—C16−1.0 (3)C19—C20—N4—C24115.3 (2)
C14—C15—C16—C171.9 (3)C22—C20—N4—C24−99.5 (3)
C14—C15—C16—C19−179.5 (2)C21—C20—N4—C24−33.2 (3)
C15—C16—C17—F4176.35 (18)C19—C20—N4—N5−67.0 (2)
C19—C16—C17—F4−2.2 (3)C22—C20—N4—N578.1 (2)
C15—C16—C17—C18−1.1 (3)C21—C20—N4—N5144.4 (2)
C19—C16—C17—C18−179.7 (2)C23—N6—C24—N40.2 (2)
F3—C13—C18—C17−177.9 (2)N5—N4—C24—N60.0 (2)
C14—C13—C18—C171.4 (3)C20—N4—C24—N6177.81 (19)
F4—C17—C18—C13−177.89 (19)N4—N5—C23—N60.4 (2)
C16—C17—C18—C13−0.5 (3)C24—N6—C23—N5−0.4 (2)
D—H···AD—HH···AD···AD—H···A
C12—H12A···O2i0.932.353.268 (2)171.
C24—H24A···O1ii0.932.373.265 (3)161.
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯ADAD—H⋯A
C12—H12A⋯O2i0.932.353.268 (2)171
C24—H24A⋯O1ii0.932.373.265 (3)161

Symmetry codes: (i) ; (ii) .

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