Literature DB >> 21522699

N-[4-Cyano-3-(trifluoro-meth-yl)phen-yl]-2-meth-oxy-benzamide.

S Nanjunda Swamy, H R Manjunath, B S Priya, M A Sridhar, K S Rangappa.   

Abstract

In the title compound, C(16)H(11)F(3)N(2)O(2), the carboxamide group connecting the two aromatic rings is in a syn-periplanar configuration; the mol-ecule is non-planar; the dihedral angle between the two aromatic rings is 13.95 (18)°. Intra-molecular N-H⋯O and C-H⋯O hydrogen bonds occur. In the crystal, mol-ecules are linked by inter-molecular C-H⋯O hydrogen bonds.

Entities:  

Year:  2010        PMID： 21522699      PMCID： PMC3050277          DOI： 10.1107/S1600536810050269

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


Related literature

For nucleosome, a repeat unit of chromatin, see: Luger & Richmond (1998 ▶). For the biological activity of substituted amide derivatives, see: Bylov et al. (1999 ▶); Gududuru et al. (2004 ▶). For the preparation of the title compound, see: Mantelingu et al. (2007 ▶). For a related structure, see: Saeed et al. (2010 ▶).

Experimental

Crystal data

C16H11F3N2O2 M = 320.27 Monoclinic, a = 15.117 (2) Å b = 13.907 (2) Å c = 14.5410 (11) Å β = 107.360 (8)° V = 2917.7 (6) Å3 Z = 8 Mo Kα radiation μ = 0.12 mm−1 T = 293 K 0.30 × 0.27 × 0.25 mm

Data collection

MacScience DIPLabo 32001 diffractometer 3420 measured reflections 1985 independent reflections 1623 reflections with I > 2σ(I) R int = 0.016 θmax = 23.3°

Refinement

R[F 2 > 2σ(F 2)] = 0.060 wR(F 2) = 0.206 S = 1.03 1985 reflections 209 parameters H-atom parameters constrained Δρmax = 0.30 e Å−3 Δρmin = −0.21 e Å−3 Data collection: XPRESS (MacScience, 2002 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and ORTEPII (Johnson, 1976) ▶; software used to prepare material for publication: SHELXL97. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810050269/jh2220sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810050269/jh2220Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C16H11F3N2O2Z = 8
Mr = 320.27F(000) = 1312
Monoclinic, C2/cDx = 1.458 Mg m−3
Hall symbol: -C 2ycMo Kα radiation, λ = 0.71073 Å
a = 15.117 (2) ŵ = 0.12 mm−1
b = 13.907 (2) ÅT = 293 K
c = 14.5410 (11) ÅBlock, colorless
β = 107.360 (8)°0.30 × 0.27 × 0.25 mm
V = 2917.7 (6) Å3
MacScience DIPLabo 32001 diffractometer1623 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.016
graphiteθmax = 23.3°, θmin = 2.3°
Detector resolution: 10.0 pixels mm-1h = −16→16
ω scansk = −15→14
3420 measured reflectionsl = −14→14
1985 independent reflections
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.060H-atom parameters constrained
wR(F2) = 0.206w = 1/[σ2(Fo2) + (0.1344P)2 + 1.7982P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.003
1985 reflectionsΔρmax = 0.30 e Å−3
209 parametersΔρmin = −0.21 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.006 (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
F190.08492 (17)−0.25311 (16)0.34995 (19)0.1107 (10)
F200.22717 (16)−0.24074 (17)0.37355 (18)0.1129 (10)
F210.1596 (3)−0.14673 (16)0.44676 (16)0.1520 (15)
O150.08614 (17)0.31412 (17)0.15351 (18)0.0881 (10)
O170.1218 (2)0.15110 (16)0.39923 (17)0.0913 (10)
N70.11310 (17)0.14525 (17)0.24161 (18)0.0674 (9)
N230.1364 (3)−0.3157 (4)0.1502 (3)0.1214 (19)
C10.1294 (2)−0.0219 (2)0.3009 (2)0.0643 (10)
C20.13454 (19)−0.1182 (2)0.2817 (2)0.0619 (10)
C30.1244 (2)−0.1500 (2)0.1890 (2)0.0675 (11)
C40.1073 (2)−0.0828 (2)0.1149 (2)0.0765 (11)
C50.1021 (2)0.0126 (2)0.1332 (2)0.0734 (12)
C60.11416 (19)0.0455 (2)0.2273 (2)0.0626 (11)
C80.1214 (2)0.1927 (2)0.3251 (2)0.0666 (11)
C90.1314 (2)0.2998 (2)0.3241 (2)0.0698 (11)
C100.1149 (2)0.3588 (2)0.2417 (3)0.0763 (14)
C110.1272 (3)0.4564 (3)0.2528 (4)0.0975 (18)
C120.1562 (3)0.4967 (3)0.3418 (4)0.113 (2)
C130.1740 (3)0.4411 (3)0.4235 (4)0.1078 (19)
C140.1608 (3)0.3431 (2)0.4140 (3)0.0852 (14)
C160.0674 (3)0.3715 (3)0.0683 (3)0.1134 (19)
C180.1520 (3)−0.1878 (2)0.3628 (2)0.0781 (14)
C220.1326 (3)−0.2568 (2)0.1652 (3)0.0644 (12)
H60.104900.181000.183200.0810*
H90.090100.058300.081500.0880*
H120.09920−0.103600.050000.0910*
H150.13630−0.000700.365500.0770*
H160.115200.496100.196500.1170*
H190.172000.303900.470700.1020*
H210.194600.468400.487000.1290*
H22A0.047400.330800.012600.1360*
H22B0.122800.404800.067700.1360*
H22C0.019700.417400.067300.1360*
H230.164500.565100.346700.1360*
U11U22U33U12U13U23
F190.1193 (18)0.0972 (16)0.124 (2)−0.0052 (13)0.0490 (14)0.0376 (13)
F200.1016 (17)0.1068 (17)0.1230 (19)0.0267 (13)0.0224 (13)0.0395 (13)
F210.310 (4)0.0802 (16)0.0651 (16)0.0290 (19)0.0550 (19)0.0146 (10)
O150.1043 (18)0.0797 (16)0.0830 (18)0.0090 (13)0.0323 (13)0.0272 (12)
O170.150 (2)0.0677 (15)0.0623 (15)−0.0031 (13)0.0410 (13)0.0051 (10)
N70.0877 (18)0.0593 (15)0.0600 (16)0.0034 (12)0.0296 (12)0.0067 (11)
N230.123 (3)0.149 (4)0.097 (3)−0.009 (3)0.040 (2)0.025 (3)
C10.0758 (19)0.0645 (18)0.0535 (17)0.0015 (14)0.0209 (13)0.0019 (13)
C20.0686 (18)0.0611 (17)0.0582 (18)0.0017 (13)0.0222 (13)0.0030 (13)
C30.0692 (18)0.0673 (19)0.069 (2)−0.0013 (14)0.0253 (14)−0.0025 (14)
C40.102 (2)0.079 (2)0.0536 (19)−0.0012 (17)0.0312 (15)−0.0052 (14)
C50.096 (2)0.070 (2)0.059 (2)0.0031 (16)0.0303 (15)0.0081 (14)
C60.0683 (18)0.0667 (19)0.0567 (18)0.0014 (13)0.0245 (13)0.0052 (13)
C80.0740 (19)0.0647 (19)0.065 (2)0.0022 (14)0.0268 (14)0.0041 (14)
C90.0688 (18)0.0625 (19)0.085 (2)0.0055 (14)0.0334 (16)0.0040 (15)
C100.069 (2)0.0632 (19)0.104 (3)0.0077 (14)0.0368 (18)0.0155 (17)
C110.103 (3)0.066 (2)0.132 (4)0.0093 (19)0.048 (2)0.020 (2)
C120.116 (3)0.058 (2)0.175 (5)0.005 (2)0.057 (3)0.001 (3)
C130.120 (3)0.075 (3)0.133 (4)0.000 (2)0.045 (3)−0.022 (2)
C140.096 (2)0.068 (2)0.096 (3)0.0034 (17)0.0353 (19)−0.0104 (18)
C160.133 (4)0.114 (3)0.098 (3)0.021 (3)0.042 (2)0.051 (2)
C180.099 (3)0.0649 (19)0.073 (2)0.0073 (19)0.0296 (17)0.0068 (15)
C220.077 (2)0.060 (2)0.062 (2)−0.0050 (18)0.0294 (15)−0.0145 (17)
F19—C181.332 (5)C8—C91.498 (4)
F20—C181.324 (5)C9—C141.387 (5)
F21—C181.321 (4)C9—C101.412 (5)
O15—C101.374 (5)C10—C111.373 (5)
O15—C161.429 (5)C11—C121.357 (8)
O17—C81.222 (4)C12—C131.375 (7)
N7—C61.404 (4)C13—C141.378 (5)
N7—C81.354 (4)C1—H150.9600
N23—C220.854 (6)C4—H120.9600
N7—H60.9600C5—H90.9600
C1—C61.389 (4)C11—H160.9600
C1—C21.375 (4)C12—H230.9600
C2—C181.487 (4)C13—H210.9600
C2—C31.383 (4)C14—H190.9600
C3—C41.391 (4)C16—H22A0.9600
C3—C221.538 (4)C16—H22B0.9600
C4—C51.360 (4)C16—H22C0.9600
C5—C61.402 (4)
F19···C222.982 (5)C22···F202.948 (5)
F19···C3i3.365 (4)C22···F19i3.230 (5)
F19···C22i3.230 (5)C22···F192.982 (5)
F20···C16ii3.351 (5)C8···H152.7500
F20···O15ii3.060 (4)C10···H62.6000
F20···C222.948 (5)C11···H22C2.7600
F20···F21iii3.088 (4)C11···H22B2.7700
F21···F20iii3.088 (4)C13···H22Ci2.9900
F19···H22Aiv2.8100C14···H22Ci3.0000
F19···H23v2.8100C16···H162.4900
F20···H23v2.8500C16···H63.0900
F21···H152.3200H6···O151.9000
F21···H9iv2.7700H6···C102.6000
O15···N72.648 (3)H6···C163.0900
O15···C9i3.406 (4)H6···H92.2300
O15···F20vi3.060 (4)H9···H62.2300
O17···C12.819 (4)H9···F21vii2.7700
O17···C4iv3.346 (4)H12···O17vii2.4100
O15···H61.9000H15···F212.3200
O17···H152.1900H15···O172.1900
O17···H192.3900H15···C82.7500
O17···H12iv2.4100H16···N23viii2.7400
N7···O152.648 (3)H16···C162.4900
N7···C8i3.448 (4)H16···H22B2.2900
N23···H16v2.7400H16···H22C2.2800
N23···H19vii2.8200H19···O172.3900
C1···O172.819 (4)H19···N23iv2.8200
C3···F19i3.365 (4)H21···H22Bix2.5300
C4···O17vii3.346 (4)H22A···F19vii2.8100
C4···C13ii3.529 (6)H22B···C112.7700
C5···C12ii3.569 (6)H22B···H162.2900
C8···N7i3.448 (4)H22B···H21x2.5300
C9···O15i3.406 (4)H22C···C112.7600
C10···C10i3.553 (5)H22C···H162.2800
C12···C5vi3.569 (6)H22C···C13i2.9900
C13···C4vi3.529 (6)H22C···C14i3.0000
C14···C16i3.557 (7)H23···F19viii2.8100
C16···C14i3.557 (7)H23···F20viii2.8500
C16···F20vi3.351 (5)
C10—O15—C16118.8 (3)C9—C14—C13121.3 (4)
C6—N7—C8127.8 (2)F19—C18—C2112.6 (3)
C6—N7—H6113.00F20—C18—F21107.2 (3)
C8—N7—H6120.00F20—C18—C2113.5 (3)
C2—C1—C6120.5 (3)F21—C18—C2113.4 (2)
C3—C2—C18120.4 (3)F19—C18—F20103.2 (2)
C1—C2—C18118.7 (2)F19—C18—F21106.1 (3)
C1—C2—C3120.9 (3)N23—C22—C3178.3 (5)
C2—C3—C22122.4 (3)C2—C1—H15120.00
C4—C3—C22118.9 (3)C6—C1—H15119.00
C2—C3—C4118.8 (3)C3—C4—H12120.00
C3—C4—C5120.8 (3)C5—C4—H12119.00
C4—C5—C6120.7 (3)C4—C5—H9120.00
N7—C6—C1124.0 (3)C6—C5—H9119.00
C1—C6—C5118.4 (3)C10—C11—H16119.00
N7—C6—C5117.6 (2)C12—C11—H16120.00
O17—C8—C9120.4 (3)C11—C12—H23119.00
O17—C8—N7122.3 (3)C13—C12—H23120.00
N7—C8—C9117.3 (2)C12—C13—H21122.00
C8—C9—C14115.3 (3)C14—C13—H21119.00
C8—C9—C10126.4 (3)C9—C14—H19119.00
C10—C9—C14118.3 (3)C13—C14—H19119.00
C9—C10—C11119.4 (4)O15—C16—H22A109.00
O15—C10—C11123.4 (4)O15—C16—H22B109.00
O15—C10—C9117.1 (2)O15—C16—H22C110.00
C10—C11—C12120.9 (5)H22A—C16—H22B109.00
C11—C12—C13121.1 (4)H22A—C16—H22C109.00
C12—C13—C14119.0 (5)H22B—C16—H22C109.00
C16—O15—C10—C11−0.3 (5)C22—C3—C4—C5−178.2 (3)
C16—O15—C10—C9179.1 (3)C2—C3—C4—C51.1 (5)
C8—N7—C6—C1−3.7 (5)C3—C4—C5—C60.2 (5)
C6—N7—C8—C9171.7 (3)C4—C5—C6—N7176.5 (3)
C8—N7—C6—C5178.5 (3)C4—C5—C6—C1−1.5 (5)
C6—N7—C8—O17−7.6 (5)N7—C8—C9—C1013.5 (5)
C6—C1—C2—C18179.3 (3)O17—C8—C9—C10−167.2 (3)
C6—C1—C2—C3−0.2 (5)O17—C8—C9—C1413.6 (5)
C2—C1—C6—N7−176.3 (3)N7—C8—C9—C14−165.8 (3)
C2—C1—C6—C51.5 (5)C8—C9—C10—C11180.0 (4)
C1—C2—C18—F210.8 (5)C14—C9—C10—O15179.8 (3)
C1—C2—C18—F19121.3 (3)C8—C9—C14—C13179.2 (4)
C1—C2—C18—F20−121.9 (3)C10—C9—C14—C13−0.2 (6)
C3—C2—C18—F21−179.7 (4)C14—C9—C10—C11−0.8 (5)
C18—C2—C3—C4179.4 (3)C8—C9—C10—O150.5 (5)
C18—C2—C3—C22−1.4 (5)O15—C10—C11—C12−179.7 (4)
C3—C2—C18—F2057.6 (4)C9—C10—C11—C120.9 (6)
C1—C2—C3—C22178.1 (3)C10—C11—C12—C13−0.1 (7)
C3—C2—C18—F19−59.2 (4)C11—C12—C13—C14−0.8 (7)
C1—C2—C3—C4−1.1 (5)C12—C13—C14—C91.0 (7)
D—H···AD—HH···AD···AD—H···A
N7—H6···O150.961.902.648 (3)133
C4—H12···O17vii0.962.413.346 (4)165
C1—H15···F210.962.322.673 (4)101
C1—H15···O170.962.192.819 (4)122
C14—H19···O170.962.392.729 (4)100
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N7—H6⋯O150.961.902.648 (3)133
C4—H12⋯O17i0.962.413.346 (4)165
C1—H15⋯O170.962.192.819 (4)122

Symmetry code: (i) .

  7 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.  The histone tails of the nucleosome.

Authors:  K Luger; T J Richmond
Journal:  Curr Opin Genet Dev       Date:  1998-04       Impact factor: 5.578

3.  Synthesis and anti-inflammatory activity of N-substituted 2-oxo-2H-1-benzopyran-3-carboxamides and their 2-iminoanalogues.

Authors: 
Journal:  Eur J Med Chem       Date:  1999-11-01       Impact factor: 6.514

4.  Synthesis and antiproliferative activity of 2-aryl-4-oxo-thiazolidin-3-yl-amides for prostate cancer.

Authors:  Veeresa Gududuru; Eunju Hurh; James T Dalton; Duane D Miller
Journal:  Bioorg Med Chem Lett       Date:  2004-11-01       Impact factor: 2.823

5.  Activation of p300 histone acetyltransferase by small molecules altering enzyme structure: probed by surface-enhanced Raman spectroscopy.

Authors:  K Mantelingu; A Hari Kishore; K Balasubramanyam; G V Pavan Kumar; M Altaf; S Nanjunda Swamy; Ruthrotha Selvi; Chandrima Das; Chandrabhas Narayana; K S Rangappa; Tapas K Kundu
Journal:  J Phys Chem B       Date:  2007-04-07       Impact factor: 2.991

6.  2-Methyl-N-p-tolyl-benzamide: a second monoclinic polymorph.

Authors:  Aamer Saeed; Rasheed Ahmad Khera; Jim Simpson
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-03-24

7.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  7 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.