Literature DB >> 22606137

(Z)-1-(2,4-Difluoro-phen-yl)-3-(4-fluoro-phen-yl)-2-(1H-1,2,4-triazol-1-yl)prop-2-en-1-one.

Ben-Tao Yin1, Jing-Song Lv, Yan Wang, Cheng-He Zhou.   

Abstract

In the title mol-ecule, C(17)H(10)F(3)N(3)O, the C=C bond connecting the triazole ring and 4-fluoro-phenyl groups adopts a Z conformation. The triazole ring forms dihedral angles of 15.3 (1) and 63.5 (1)°, with the 2,4-difluoro-substituted and 4-fluoro-substituted benzene rings, respectively. The dihedral angle between the two benzene rings is 51.8 (1)°.

Entities:  

Year:  2012        PMID： 22606137      PMCID： PMC3344134          DOI： 10.1107/S1600536812012123

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


Related literature

For the pharmacological activity of triazole derivatives, see: Wang & Zhou (2011 ▶); Zhou & Wang (2012 ▶). For the biological activity of chalcones, see: Jin et al. (2010 ▶). For related structures, see: Wang et al. (2009 ▶); Yan et al. (2009 ▶). For the synthesis, see: Yan et al. (2009 ▶).

Experimental

Crystal data

C17H10F3N3O M = 329.28 Monoclinic, a = 11.735 (6) Å b = 7.698 (4) Å c = 17.065 (7) Å β = 110.45 (3)° V = 1444.4 (12) Å3 Z = 4 Mo Kα radiation μ = 0.12 mm−1 T = 293 K 0.19 × 0.17 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.977, T max = 0.980 7601 measured reflections 2840 independent reflections 2095 reflections with I > 2σ(I) R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.042 wR(F 2) = 0.100 S = 1.01 2840 reflections 217 parameters H-atom parameters constrained Δρmax = 0.15 e Å−3 Δρmin = −0.21 e Å−3 Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812012123/lh5435sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812012123/lh5435Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812012123/lh5435Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C17H10F3N3OF(000) = 672
Mr = 329.28Dx = 1.514 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2158 reflections
a = 11.735 (6) Åθ = 2.9–23.2°
b = 7.698 (4) ŵ = 0.12 mm−1
c = 17.065 (7) ÅT = 293 K
β = 110.45 (3)°Block, colourless
V = 1444.4 (12) Å30.19 × 0.17 × 0.16 mm
Z = 4
Bruker APEXII CCD diffractometer2840 independent reflections
Radiation source: fine-focus sealed tube2095 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
φ and ω scansθmax = 26.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −14→14
Tmin = 0.977, Tmax = 0.980k = −9→9
7601 measured reflectionsl = −21→16
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.0398P)2 + 0.3484P] where P = (Fo2 + 2Fc2)/3
2840 reflections(Δ/σ)max = 0.001
217 parametersΔρmax = 0.15 e Å−3
0 restraintsΔρmin = −0.21 e Å−3
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
F1−0.10204 (11)0.63601 (19)0.88238 (9)0.0882 (4)
F20.09918 (11)0.6680 (2)0.69415 (7)0.0836 (4)
F30.87808 (11)1.03042 (17)1.09542 (8)0.0816 (4)
O10.29519 (13)0.4323 (2)0.74119 (9)0.0862 (5)
N10.52550 (12)0.49839 (18)0.83262 (8)0.0416 (3)
N20.61373 (13)0.40221 (19)0.88775 (9)0.0498 (4)
N30.64451 (15)0.4248 (2)0.76604 (10)0.0619 (5)
C1−0.00130 (16)0.6098 (3)0.86429 (13)0.0551 (5)
C2−0.00402 (16)0.6532 (3)0.78670 (12)0.0579 (5)
H2A−0.07320.70000.74690.070*
C30.09943 (16)0.6248 (2)0.77016 (10)0.0508 (4)
C40.20312 (15)0.5587 (2)0.82741 (10)0.0432 (4)
C50.20019 (16)0.5199 (2)0.90521 (11)0.0493 (4)
H5A0.26960.47630.94600.059*
C60.09753 (18)0.5442 (3)0.92381 (12)0.0576 (5)
H6A0.09580.51610.97640.069*
C70.30928 (16)0.5142 (2)0.80365 (11)0.0487 (4)
C80.43130 (14)0.5720 (2)0.85556 (9)0.0392 (4)
C90.54611 (17)0.5086 (3)0.76135 (11)0.0550 (5)
H9A0.49680.56790.71420.066*
C100.68092 (17)0.3624 (3)0.84397 (12)0.0565 (5)
H10A0.75040.29430.86560.068*
C110.45564 (14)0.6885 (2)0.91621 (9)0.0393 (4)
H11A0.39000.72030.93170.047*
C120.56903 (15)0.7736 (2)0.96193 (9)0.0382 (4)
C130.65828 (16)0.8061 (2)0.92821 (10)0.0458 (4)
H13A0.64770.76760.87450.055*
C140.76122 (17)0.8936 (2)0.97250 (11)0.0528 (5)
H14A0.82060.91660.94940.063*
C150.77542 (17)0.9468 (2)1.05143 (12)0.0529 (5)
C160.69124 (17)0.9189 (2)1.08757 (11)0.0509 (4)
H16A0.70390.95591.14190.061*
C170.58720 (16)0.8347 (2)1.04174 (10)0.0443 (4)
H17A0.52680.81791.06460.053*
U11U22U33U12U13U23
F10.0522 (7)0.1184 (11)0.1063 (10)0.0076 (7)0.0433 (7)−0.0049 (9)
F20.0626 (8)0.1346 (12)0.0478 (6)−0.0146 (7)0.0117 (5)0.0233 (7)
F30.0704 (8)0.0765 (8)0.0851 (9)−0.0227 (7)0.0113 (7)−0.0198 (7)
O10.0622 (9)0.1310 (14)0.0718 (9)−0.0220 (9)0.0314 (8)−0.0551 (10)
N10.0459 (8)0.0450 (8)0.0399 (7)0.0012 (7)0.0225 (6)−0.0033 (6)
N20.0484 (9)0.0524 (9)0.0539 (9)0.0084 (7)0.0243 (7)0.0022 (7)
N30.0605 (11)0.0776 (12)0.0593 (10)−0.0020 (9)0.0359 (9)−0.0177 (9)
C10.0413 (11)0.0612 (12)0.0693 (13)−0.0024 (9)0.0276 (9)−0.0047 (10)
C20.0383 (10)0.0628 (12)0.0636 (12)−0.0012 (9)0.0063 (9)0.0031 (10)
C30.0467 (11)0.0618 (11)0.0412 (9)−0.0114 (9)0.0120 (8)0.0041 (9)
C40.0416 (10)0.0451 (9)0.0442 (9)−0.0038 (8)0.0166 (8)−0.0025 (8)
C50.0488 (10)0.0527 (11)0.0484 (10)0.0081 (9)0.0194 (8)0.0069 (8)
C60.0578 (12)0.0678 (13)0.0562 (11)0.0033 (10)0.0312 (10)0.0060 (10)
C70.0496 (10)0.0573 (11)0.0432 (9)−0.0040 (9)0.0212 (8)−0.0076 (9)
C80.0428 (9)0.0425 (9)0.0371 (8)0.0045 (7)0.0202 (7)0.0018 (7)
C90.0610 (12)0.0677 (12)0.0429 (10)−0.0030 (10)0.0264 (9)−0.0078 (9)
C100.0490 (11)0.0603 (12)0.0664 (12)0.0040 (9)0.0279 (10)−0.0105 (10)
C110.0416 (9)0.0414 (9)0.0387 (8)0.0064 (7)0.0188 (7)0.0038 (7)
C120.0442 (9)0.0348 (8)0.0376 (8)0.0078 (7)0.0167 (7)0.0023 (7)
C130.0543 (11)0.0454 (10)0.0409 (9)−0.0011 (9)0.0206 (8)−0.0016 (8)
C140.0535 (11)0.0493 (11)0.0609 (11)−0.0043 (9)0.0266 (9)0.0004 (9)
C150.0527 (11)0.0401 (10)0.0560 (11)−0.0032 (9)0.0065 (9)−0.0048 (9)
C160.0632 (12)0.0448 (10)0.0422 (9)0.0062 (9)0.0151 (9)−0.0045 (8)
C170.0534 (11)0.0402 (9)0.0432 (9)0.0070 (8)0.0218 (8)−0.0009 (8)
F1—C11.337 (2)C5—H5A0.9300
F2—C31.3382 (19)C6—H6A0.9300
F3—C151.341 (2)C7—C81.465 (2)
O1—C71.199 (2)C8—C111.323 (2)
N1—C91.323 (2)C9—H9A0.9300
N1—N21.351 (2)C10—H10A0.9300
N1—C81.414 (2)C11—C121.443 (2)
N2—C101.298 (2)C11—H11A0.9300
N3—C91.300 (2)C12—C131.383 (2)
N3—C101.336 (2)C12—C171.385 (2)
C1—C61.345 (3)C13—C141.359 (3)
C1—C21.355 (3)C13—H13A0.9300
C2—C31.357 (3)C14—C151.361 (2)
C2—H2A0.9300C14—H14A0.9300
C3—C41.365 (2)C15—C161.352 (3)
C4—C51.373 (2)C16—C171.362 (3)
C4—C71.479 (2)C16—H16A0.9300
C5—C61.362 (2)C17—H17A0.9300
C9—N1—N2109.34 (14)N1—C8—C7113.87 (14)
C9—N1—C8130.00 (15)N3—C9—N1110.95 (18)
N2—N1—C8120.66 (12)N3—C9—H9A124.5
C10—N2—N1101.56 (14)N1—C9—H9A124.5
C9—N3—C10102.01 (15)N2—C10—N3116.13 (18)
F1—C1—C6118.75 (17)N2—C10—H10A121.9
F1—C1—C2117.86 (18)N3—C10—H10A121.9
C6—C1—C2123.38 (17)C8—C11—C12129.55 (15)
C1—C2—C3116.50 (18)C8—C11—H11A115.2
C1—C2—H2A121.7C12—C11—H11A115.2
C3—C2—H2A121.7C13—C12—C17117.96 (16)
F2—C3—C2117.55 (17)C13—C12—C11123.14 (14)
F2—C3—C4119.07 (16)C17—C12—C11118.80 (14)
C2—C3—C4123.36 (16)C14—C13—C12120.92 (16)
C3—C4—C5117.12 (16)C14—C13—H13A119.5
C3—C4—C7121.05 (15)C12—C13—H13A119.5
C5—C4—C7121.54 (16)C13—C14—C15118.50 (17)
C6—C5—C4121.25 (17)C13—C14—H14A120.8
C6—C5—H5A119.4C15—C14—H14A120.8
C4—C5—H5A119.4F3—C15—C16118.53 (17)
C1—C6—C5118.37 (17)F3—C15—C14118.29 (18)
C1—C6—H6A120.8C16—C15—C14123.18 (17)
C5—C6—H6A120.8C15—C16—C17117.69 (16)
O1—C7—C8119.94 (16)C15—C16—H16A121.2
O1—C7—C4119.85 (17)C17—C16—H16A121.2
C8—C7—C4120.21 (15)C16—C17—C12121.70 (16)
C11—C8—N1120.81 (15)C16—C17—H17A119.2
C11—C8—C7125.23 (15)C12—C17—H17A119.2
C9—N1—N2—C100.01 (19)O1—C7—C8—C11166.70 (18)
C8—N1—N2—C10−179.18 (15)C4—C7—C8—C11−12.5 (3)
F1—C1—C2—C3−179.89 (17)O1—C7—C8—N1−9.9 (3)
C6—C1—C2—C31.0 (3)C4—C7—C8—N1170.88 (14)
C1—C2—C3—F2−179.47 (17)C10—N3—C9—N10.6 (2)
C1—C2—C3—C4−1.0 (3)N2—N1—C9—N3−0.4 (2)
F2—C3—C4—C5178.52 (16)C8—N1—C9—N3178.68 (16)
C2—C3—C4—C50.1 (3)N1—N2—C10—N30.4 (2)
F2—C3—C4—C7−7.6 (3)C9—N3—C10—N2−0.6 (2)
C2—C3—C4—C7173.93 (18)N1—C8—C11—C127.1 (3)
C3—C4—C5—C60.9 (3)C7—C8—C11—C12−169.35 (16)
C7—C4—C5—C6−172.91 (17)C8—C11—C12—C1329.3 (3)
F1—C1—C6—C5−179.18 (17)C8—C11—C12—C17−154.43 (17)
C2—C1—C6—C5−0.1 (3)C17—C12—C13—C140.8 (2)
C4—C5—C6—C1−0.9 (3)C11—C12—C13—C14177.03 (16)
C3—C4—C7—O1−46.8 (3)C12—C13—C14—C150.8 (3)
C5—C4—C7—O1126.8 (2)C13—C14—C15—F3178.87 (16)
C3—C4—C7—C8132.36 (19)C13—C14—C15—C16−0.9 (3)
C5—C4—C7—C8−54.0 (2)F3—C15—C16—C17179.59 (15)
C9—N1—C8—C11−116.2 (2)C14—C15—C16—C17−0.6 (3)
N2—N1—C8—C1162.8 (2)C15—C16—C17—C122.3 (3)
C9—N1—C8—C760.6 (2)C13—C12—C17—C16−2.4 (2)
N2—N1—C8—C7−120.40 (17)C11—C12—C17—C16−178.81 (15)
  4 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

Review 2.  Recent researches in triazole compounds as medicinal drugs.

Authors:  C-H Zhou; Y Wang
Journal:  Curr Med Chem       Date:  2012       Impact factor: 4.530

3.  (Z)-1-(2,4-Difluoro-phen-yl)-3-phenyl-2-(1H-1,2,4-triazol-1-yl)prop-2-en-1-one.

Authors:  Cong-Yan Yan; Guang-Zhou Wang; Cheng-He Zhou
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-07-31

4.  (Z)-3-(9-Anthryl)-1-(4-chloro-phen-yl)-2-(4-nitro-1H-imidazol-1-yl)prop-2-en-1-one.

Authors:  Guang-Zhou Wang; Yi-Hui Lu; Cheng-He Zhou; Yi-Yi Zhang
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-04-25
  4 in total
  1 in total

1.  (Z)-1,3-Bis(4-chloro-phen-yl)-2-(1H-1,2,4-triazol-1-yl)prop-2-en-1-one.

Authors:  Ling-Ling Dai; Ben-Tao Yin; Jing-Song Lv; Sheng-Feng Cui; Cheng-He Zhou
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-04-21
  1 in total

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