Literature DB >> 23284482

4-Bromo-2-[(E)-{[4-nitro-2-(trifluoro-meth-yl)phen-yl]imino}-meth-yl]phenol.

Mehmet Akkurt1, Alan R Kennedy, Shaaban K Mohamed, Antar A Abdelhamid, Gary J Miller.   

Abstract

Except two F atoms of the -CF(3) group, the title compound, C(14)H(8)BrF(3)N(2)O(3), has an almost planar conformation, the dihedral angle between the aromatic rings being 3.60 (16)°. The mol-ecule adopts the enol-imine tautomeric form, with an intra-molecular O-H⋯N hydrogen bond, which generates an S(6) ring motif. In the crystal, face-to-face π-π stacking [centroid-centroid distances = 3.669 (2) and 3.732 (2) Å] between the aromatic rings of the mol-ecules, which lie in sheets parallel to (202), help to establish the packing.

Entities:  

Year:  2012        PMID： 23284482      PMCID： PMC3515262          DOI： 10.1107/S1600536812042262

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


Related literature

For the biological activity of fluorine-containing compounds, see: Blair et al. (2000 ▶); Chawla et al. (2012 ▶); Bella et al. (2004 ▶); Chandra & Kumar (2005 ▶); Yang et al. (2000 ▶). For the synthesis of a similar azomethine compound, see: Mohamed et al. (2012 ▶). For the graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C14H8BrF3N2O3 M = 389.12 Monoclinic, a = 7.3596 (5) Å b = 16.4625 (10) Å c = 11.2599 (6) Å β = 94.955 (5)° V = 1359.12 (14) Å3 Z = 4 Mo Kα radiation μ = 3.08 mm−1 T = 123 K 0.20 × 0.18 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.546, T max = 0.575 6329 measured reflections 3149 independent reflections 2165 reflections with I > 2σ(I) R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.050 wR(F 2) = 0.090 S = 1.02 3149 reflections 203 parameters 1 restraint H-atom parameters constrained Δρmax = 0.51 e Å−3 Δρmin = −0.59 e Å−3 Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶). Click here for additional data file. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812042262/xu5632sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812042262/xu5632Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C14H8BrF3N2O3F(000) = 768
Mr = 389.12Dx = 1.902 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1836 reflections
a = 7.3596 (5) Åθ = 3.2–29.0°
b = 16.4625 (10) ŵ = 3.08 mm−1
c = 11.2599 (6) ÅT = 123 K
β = 94.955 (5)°Cut rod, yellow
V = 1359.12 (14) Å30.20 × 0.18 × 0.18 mm
Z = 4
Oxford Diffraction Xcalibur Eos diffractometer3149 independent reflections
Radiation source: Enhance (Mo) X-ray Source2165 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
Detector resolution: 16.0727 pixels mm-1θmax = 29.0°, θmin = 3.2°
ω scansh = −9→8
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)k = −18→22
Tmin = 0.546, Tmax = 0.575l = −14→15
6329 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0233P)2] where P = (Fo2 + 2Fc2)/3
3149 reflections(Δ/σ)max < 0.001
203 parametersΔρmax = 0.51 e Å−3
1 restraintΔρmin = −0.59 e Å−3
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
Br10.40760 (6)0.10935 (3)0.52512 (3)0.0305 (2)
F10.7671 (3)0.08414 (14)1.28090 (17)0.0313 (8)
F21.0022 (3)0.05148 (15)1.39501 (17)0.0404 (9)
F31.0339 (3)0.09587 (14)1.21958 (18)0.0321 (8)
O11.1326 (3)−0.22498 (18)1.4389 (2)0.0299 (9)
O21.0746 (4)−0.31205 (17)1.2960 (2)0.0286 (9)
O30.7242 (4)0.17073 (17)1.02757 (19)0.0262 (9)
N10.7788 (4)0.01384 (19)1.0499 (2)0.0168 (7)
N21.0692 (4)−0.2434 (2)1.3380 (3)0.0231 (11)
C10.6384 (5)0.0741 (2)0.8725 (3)0.0160 (11)
C20.5635 (4)0.0613 (2)0.7551 (3)0.0185 (11)
C30.5065 (5)0.1256 (3)0.6850 (3)0.0192 (11)
C40.5184 (5)0.2040 (3)0.7277 (3)0.0220 (12)
C50.5917 (5)0.2182 (2)0.8437 (3)0.0210 (12)
C60.6520 (5)0.1540 (2)0.9156 (3)0.0176 (11)
C70.6997 (4)0.0045 (2)0.9437 (3)0.0168 (7)
C80.8434 (4)−0.0537 (2)1.1180 (3)0.0145 (11)
C90.9215 (5)−0.0375 (2)1.2358 (3)0.0158 (11)
C100.9916 (4)−0.1002 (2)1.3070 (3)0.0185 (11)
C110.9869 (4)−0.1777 (2)1.2628 (3)0.0165 (11)
C120.9119 (5)−0.1958 (2)1.1491 (3)0.0194 (12)
C130.8421 (5)−0.1338 (2)1.0781 (3)0.0190 (11)
C140.9282 (5)0.0480 (3)1.2828 (3)0.0225 (12)
H1O0.757200.127301.062200.0390*
H20.552300.007600.724400.0220*
H40.476700.248100.678200.0260*
H50.600300.272200.873600.0250*
H70.68160−0.048700.912100.0200*
H101.04260−0.089701.385900.0220*
H120.90880−0.250201.120800.0230*
H130.79150−0.145700.999600.0230*
U11U22U33U12U13U23
Br10.0418 (3)0.0288 (3)0.0189 (2)0.0038 (2)−0.0083 (2)0.0014 (2)
F10.0389 (14)0.0225 (14)0.0323 (13)0.0074 (12)0.0023 (10)−0.0076 (11)
F20.0708 (18)0.0249 (16)0.0215 (12)0.0036 (15)−0.0195 (11)−0.0031 (11)
F30.0407 (14)0.0180 (14)0.0370 (13)−0.0091 (12)−0.0002 (10)−0.0010 (11)
O10.0367 (17)0.0287 (18)0.0221 (14)−0.0014 (15)−0.0098 (11)0.0078 (14)
O20.0364 (17)0.0168 (17)0.0325 (15)0.0032 (15)0.0019 (12)0.0047 (13)
O30.0387 (17)0.0174 (16)0.0206 (14)0.0006 (15)−0.0082 (11)0.0014 (12)
N10.0190 (12)0.0145 (13)0.0168 (11)−0.0024 (11)0.0008 (9)0.0019 (11)
N20.0215 (18)0.023 (2)0.0249 (18)0.0009 (17)0.0021 (13)0.0074 (16)
C10.0146 (19)0.017 (2)0.0164 (18)−0.0012 (17)0.0015 (14)0.0063 (17)
C20.0190 (19)0.015 (2)0.021 (2)−0.0019 (18)−0.0007 (14)−0.0029 (17)
C30.0156 (19)0.024 (2)0.0178 (19)−0.0020 (18)−0.0004 (14)0.0031 (17)
C40.020 (2)0.023 (2)0.023 (2)−0.0011 (19)0.0022 (15)0.0039 (18)
C50.025 (2)0.013 (2)0.025 (2)0.0003 (18)0.0022 (15)0.0016 (17)
C60.0170 (19)0.016 (2)0.0198 (19)−0.0017 (18)0.0014 (14)0.0005 (17)
C70.0190 (12)0.0145 (13)0.0168 (11)−0.0024 (11)0.0008 (9)0.0019 (11)
C80.0136 (18)0.016 (2)0.0139 (18)0.0001 (17)0.0015 (13)0.0036 (16)
C90.0169 (19)0.016 (2)0.0144 (18)−0.0003 (17)0.0015 (14)0.0020 (16)
C100.0168 (19)0.025 (2)0.0136 (18)−0.0014 (19)0.0009 (13)0.0002 (17)
C110.0138 (19)0.018 (2)0.0177 (18)0.0029 (17)0.0018 (14)0.0057 (17)
C120.022 (2)0.012 (2)0.024 (2)−0.0020 (18)0.0015 (15)−0.0028 (17)
C130.028 (2)0.014 (2)0.0139 (18)−0.0011 (18)−0.0037 (15)−0.0018 (16)
C140.029 (2)0.017 (2)0.020 (2)−0.001 (2)−0.0071 (16)0.0025 (17)
Br1—C31.902 (3)C4—C51.389 (5)
F1—C141.325 (5)C5—C61.381 (5)
F2—C141.333 (4)C8—C131.393 (5)
F3—C141.352 (5)C8—C91.425 (5)
O1—N21.228 (4)C9—C101.379 (5)
O2—N21.227 (4)C9—C141.503 (6)
O3—C61.354 (4)C10—C111.369 (5)
O3—H1O0.8400C11—C121.382 (5)
N1—C71.293 (4)C12—C131.369 (5)
N1—C81.410 (4)C2—H20.9500
N2—C111.471 (5)C4—H40.9500
C1—C61.403 (5)C5—H50.9500
C1—C71.448 (5)C7—H70.9500
C1—C21.404 (5)C10—H100.9500
C2—C31.365 (5)C12—H120.9500
C3—C41.378 (7)C13—H130.9500
C6—O3—H1O109.00N2—C11—C10118.7 (3)
C7—N1—C8120.9 (3)C10—C11—C12122.2 (3)
O1—N2—C11117.1 (3)N2—C11—C12119.1 (3)
O2—N2—C11118.7 (3)C11—C12—C13118.7 (3)
O1—N2—O2124.2 (3)C8—C13—C12121.7 (3)
C2—C1—C7118.8 (3)F1—C14—F3106.5 (3)
C6—C1—C7122.8 (3)F1—C14—C9114.4 (3)
C2—C1—C6118.5 (3)F1—C14—F2106.7 (3)
C1—C2—C3120.3 (3)F2—C14—C9111.9 (3)
Br1—C3—C2120.8 (3)F3—C14—C9111.3 (3)
Br1—C3—C4118.0 (3)F2—C14—F3105.5 (3)
C2—C3—C4121.2 (3)C1—C2—H2120.00
C3—C4—C5119.6 (4)C3—C2—H2120.00
C4—C5—C6120.1 (3)C3—C4—H4120.00
O3—C6—C5118.1 (3)C5—C4—H4120.00
C1—C6—C5120.3 (3)C4—C5—H5120.00
O3—C6—C1121.6 (3)C6—C5—H5120.00
N1—C7—C1120.8 (3)N1—C7—H7120.00
N1—C8—C13125.4 (3)C1—C7—H7120.00
C9—C8—C13117.9 (3)C9—C10—H10120.00
N1—C8—C9116.7 (3)C11—C10—H10120.00
C8—C9—C14120.1 (3)C11—C12—H12121.00
C10—C9—C14119.8 (3)C13—C12—H12121.00
C8—C9—C10120.1 (3)C8—C13—H13119.00
C9—C10—C11119.3 (3)C12—C13—H13119.00
C8—N1—C7—C1−178.1 (3)C4—C5—C6—C1−0.5 (6)
C7—N1—C8—C9−177.4 (3)N1—C8—C9—C10−178.5 (3)
C7—N1—C8—C134.8 (5)N1—C8—C9—C141.4 (5)
O1—N2—C11—C102.4 (4)C13—C8—C9—C10−0.5 (5)
O1—N2—C11—C12−179.2 (3)C13—C8—C9—C14179.3 (3)
O2—N2—C11—C10−175.8 (3)N1—C8—C13—C12178.3 (3)
O2—N2—C11—C122.5 (5)C9—C8—C13—C120.5 (5)
C6—C1—C2—C30.3 (5)C8—C9—C10—C110.7 (5)
C7—C1—C2—C3−179.2 (3)C14—C9—C10—C11−179.2 (3)
C2—C1—C6—O3−179.5 (3)C8—C9—C14—F157.2 (4)
C2—C1—C6—C50.4 (5)C8—C9—C14—F2178.7 (3)
C7—C1—C6—O30.0 (6)C8—C9—C14—F3−63.6 (4)
C7—C1—C6—C5179.9 (3)C10—C9—C14—F1−122.9 (3)
C2—C1—C7—N1176.1 (3)C10—C9—C14—F2−1.5 (5)
C6—C1—C7—N1−3.4 (5)C10—C9—C14—F3116.3 (4)
C1—C2—C3—Br1179.2 (3)C9—C10—C11—N2177.4 (3)
C1—C2—C3—C4−0.9 (5)C9—C10—C11—C12−0.8 (5)
Br1—C3—C4—C5−179.3 (3)N2—C11—C12—C13−177.5 (3)
C2—C3—C4—C50.8 (6)C10—C11—C12—C130.8 (5)
C3—C4—C5—C6−0.1 (6)C11—C12—C13—C8−0.6 (5)
C4—C5—C6—O3179.3 (3)
D—H···AD—HH···AD···AD—H···A
O3—H1O···N10.841.882.623 (4)146
C10—H10···F20.952.352.685 (4)100
C13—H13···O1i0.952.503.134 (4)125
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
O3—H1O⋯N10.841.882.623 (4)146
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