organic compounds
N-Benzyl-2-(2-bromophenyl)-2-(2-nitrophenoxy)acetamide
aLaboratory of Asymmetric Catalysis and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou, Zhejiang 310027, People's Republic of China
*Correspondence e-mail: wyz@zju.edu.cn
The title compound, C21H17BrN2O4, a 2-phenoxy-2-phenylacetamide derivative, exhibits a stereogenic center but crystallizes as a racemate as indicated by the centrosymmetric In the molecular structure, the nitro-substituted benzene ring is coplanar [dihedral angle = 12.9 (1)°] with the plane formed by H—N—C(=O)—C=O due to intramolecular N—H⋯O hydrogen-bond interactions.
Related literature
For the synthesis and biological activity of 2-phenoxy-2-phenyl-acetamides, see: Dorsch et al. (2002); Wang et al. (2010); Lau et al. (2003). For additional synthetic procedures, see: Dai & Li (2007).
Experimental
Crystal data
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Refinement
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Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell 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: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2.
Supporting information
https://doi.org/10.1107/S1600536810014996/im2196sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810014996/im2196Isup2.hkl
To a solution of 2-nitrophenol (28 mg, 0.20 mmol) in anhydrous MeCN (0.2 mL, 1.0 M) in a 2-mL tube were added 2-bromobenzaldehyde (48.0 mg, 0.26 mmol), N,N-diisopropylethylamine (0.004 mL, 0.02 mmol, 10 mol%), and benzyl isocyanide (0.037 mL, 0.30 mmol, 1.5 equiv). The resulting mixture was stirred at 352 K under a nitrogen atmosphere for 72 h. The reaction mixture was concentrated under reduced pressure and the residue was then puried by flash
(silica gel, eluted with 20% EtOAc in light petroleum ether) to afford the title compound as a yellow solid (84.0 mg, 95%). mp 418-419 K (EtOAc-hexane). Single crystals suitable for X-ray diffraction of the title compound were grown in the mixed solvent of EtOAc and hexane (v:v = 1:3) at 283 K.The H atoms were placed in calculated positions with C—H = 0.93-0.98 Å, and included in the
in riding model, with Uiso(H) = 1.2Ueq (carrier atom).The title compound, C21H17BrN2O4, is a 2-phenoxy-2-phenyl-acetamide derivative, which have been reported to deliver various biological activities such as acting as inhibitors of the
factors Xa and IXa and are therefore used for the therapy of thromboembolic disorder and as safe and effective anticoagulants for myocardial infarction and ischemic disease (Dorsch, et al.; 2002, Wang et al., 2010). They are also active as glucokinase activators rendering their use for the treatment of type I and type II diabetes (Lau, et al.; 2003).The title compound has recently been obtained during the Lewis base-catalyzed phenol-Passerini three-component reaction (phenol-P-3CR) from nitrophenols, aryl α-carbon. The nitro-substituted benzene moiety is coplanar with the plane formed by atoms H22-N22-C8-C9-O2 due to intramolecular hydrogen bond interactions between N22-H22···O2 and N22-H22···O25.
and alkyl (Dai & Li; 2007). We report here its In the molecular structure (Fig. 1), there is one benzyl group linked to the amide nitrogen atom. In addition, one 2-bromobenzene and a 2-nitrophenoxy substituents are attached to theFor the synthesis and biological activity of 2-phenoxy-2-phenyl-acetamides, see: Dorsch et al. (2002); Wang et al. (2010); Lau et al. (2003). For additional synthetic procedures, see: Dai & Li (2007).
Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell
CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).Fig. 1. Molecular structure of (1). Displacement ellipsoids are drawn at the 40% probability level and H atoms are shown as small circles of arbitary radii. |
C21H17BrN2O4 | Z = 2 |
Mr = 441.28 | F(000) = 448 |
Triclinic, P1 | Dx = 1.524 Mg m−3 |
Hall symbol: -P 1 | Cu Kα radiation, λ = 1.54184 Å |
a = 7.5818 (5) Å | Cell parameters from 3052 reflections |
b = 10.4650 (7) Å | θ = 3.5–66.9° |
c = 13.1095 (10) Å | µ = 3.17 mm−1 |
α = 73.939 (6)° | T = 293 K |
β = 82.878 (6)° | Block, colorless |
γ = 74.447 (6)° | 0.38 × 0.26 × 0.18 mm |
V = 961.56 (12) Å3 |
Oxford Diffraction Xcalibur Atlas Gemini ultra diffractometer | 3363 independent reflections |
Radiation source: fine-focus sealed tube | 2522 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
Detector resolution: 10.3592 pixels mm-1 | θmax = 66.6°, θmin = 3.5° |
ω scans | h = −9→8 |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009) | k = −11→12 |
Tmin = 0.427, Tmax = 0.565 | l = −15→15 |
7135 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.105 | w = 1/[σ2(Fo2) + (0.0523P)2 + 0.350P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
3363 reflections | Δρmax = 0.37 e Å−3 |
254 parameters | Δρmin = −0.39 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0258 (10) |
C21H17BrN2O4 | γ = 74.447 (6)° |
Mr = 441.28 | V = 961.56 (12) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.5818 (5) Å | Cu Kα radiation |
b = 10.4650 (7) Å | µ = 3.17 mm−1 |
c = 13.1095 (10) Å | T = 293 K |
α = 73.939 (6)° | 0.38 × 0.26 × 0.18 mm |
β = 82.878 (6)° |
Oxford Diffraction Xcalibur Atlas Gemini ultra diffractometer | 3363 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009) | 2522 reflections with I > 2σ(I) |
Tmin = 0.427, Tmax = 0.565 | Rint = 0.030 |
7135 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.105 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.37 e Å−3 |
3363 reflections | Δρmin = −0.39 e Å−3 |
254 parameters |
Experimental. (CrysAlis Pro; Oxford Diffraction, 2009) Version 1.171.33.53 (release 17-11-2009 CrysAlis171 .NET) (compiled Nov 17 2009,16:58:22) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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. |
x | y | z | Uiso*/Ueq | ||
Br27 | 0.67572 (5) | 0.56595 (4) | 0.87665 (3) | 0.0848 (2) | |
O2 | 0.3651 (3) | 0.99683 (19) | 0.82814 (14) | 0.0599 (5) | |
O24 | 0.6787 (3) | 0.8846 (3) | 0.63093 (18) | 0.0856 (7) | |
O25 | 0.2519 (5) | 1.2538 (2) | 0.8109 (2) | 0.1010 (9) | |
O26 | 0.0566 (5) | 1.3176 (3) | 0.9264 (3) | 0.1318 (13) | |
N22 | 0.5004 (4) | 1.0913 (3) | 0.64616 (19) | 0.0712 (7) | |
H22 | 0.4153 | 1.1318 | 0.6846 | 0.085* | |
N23 | 0.1698 (4) | 1.2288 (3) | 0.8964 (2) | 0.0653 (7) | |
C1 | 0.6438 (6) | 1.3641 (4) | 0.5979 (3) | 0.0878 (11) | |
H1 | 0.5190 | 1.4028 | 0.6064 | 0.105* | |
C2 | 0.7724 (10) | 1.4280 (5) | 0.6178 (3) | 0.1174 (18) | |
H2 | 0.7341 | 1.5090 | 0.6395 | 0.141* | |
C3 | 0.9541 (11) | 1.3690 (8) | 0.6046 (4) | 0.126 (2) | |
H3 | 1.0401 | 1.4101 | 0.6182 | 0.152* | |
C4 | 1.0118 (7) | 1.2529 (7) | 0.5724 (4) | 0.1164 (18) | |
H4 | 1.1365 | 1.2150 | 0.5628 | 0.140* | |
C5 | 0.8863 (5) | 1.1907 (4) | 0.5537 (3) | 0.0829 (10) | |
H5 | 0.9267 | 1.1098 | 0.5320 | 0.099* | |
C6 | 0.7016 (4) | 1.2457 (4) | 0.5664 (2) | 0.0629 (8) | |
C7 | 0.5676 (6) | 1.1746 (5) | 0.5464 (3) | 0.0911 (13) | |
H7B | 0.4646 | 1.2424 | 0.5108 | 0.109* | |
H7A | 0.6259 | 1.1159 | 0.4998 | 0.109* | |
C8 | 0.5655 (4) | 0.9562 (4) | 0.6794 (2) | 0.0615 (8) | |
C9 | 0.4855 (4) | 0.8876 (3) | 0.7880 (2) | 0.0515 (6) | |
H9 | 0.5849 | 0.8396 | 0.8363 | 0.062* | |
C10 | 0.3835 (4) | 0.7874 (3) | 0.7772 (2) | 0.0477 (6) | |
C11 | 0.4463 (4) | 0.6461 (3) | 0.8127 (2) | 0.0577 (7) | |
C12 | 0.3448 (5) | 0.5585 (3) | 0.8030 (3) | 0.0745 (9) | |
H12 | 0.3896 | 0.4642 | 0.8271 | 0.089* | |
C13 | 0.1799 (5) | 0.6103 (4) | 0.7584 (3) | 0.0750 (9) | |
H13 | 0.1110 | 0.5511 | 0.7532 | 0.090* | |
C14 | 0.1141 (4) | 0.7491 (4) | 0.7209 (2) | 0.0673 (8) | |
H14 | 0.0017 | 0.7842 | 0.6895 | 0.081* | |
C15 | 0.2163 (4) | 0.8368 (3) | 0.7301 (2) | 0.0558 (7) | |
H15 | 0.1716 | 0.9309 | 0.7040 | 0.067* | |
C16 | 0.3115 (4) | 0.9775 (3) | 0.93255 (19) | 0.0460 (6) | |
C17 | 0.3463 (4) | 0.8503 (3) | 1.0060 (2) | 0.0544 (7) | |
H17 | 0.4134 | 0.7728 | 0.9846 | 0.065* | |
C18 | 0.2821 (4) | 0.8388 (3) | 1.1098 (2) | 0.0631 (8) | |
H18 | 0.3077 | 0.7534 | 1.1583 | 0.076* | |
C19 | 0.1805 (4) | 0.9514 (4) | 1.1434 (2) | 0.0698 (9) | |
H19 | 0.1373 | 0.9420 | 1.2140 | 0.084* | |
C20 | 0.1435 (4) | 1.0772 (3) | 1.0723 (2) | 0.0628 (8) | |
H20 | 0.0739 | 1.1537 | 1.0943 | 0.075* | |
C21 | 0.2096 (4) | 1.0908 (3) | 0.9674 (2) | 0.0488 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br27 | 0.0661 (3) | 0.0668 (3) | 0.1161 (4) | 0.00496 (17) | −0.0286 (2) | −0.0247 (2) |
O2 | 0.0875 (14) | 0.0447 (10) | 0.0454 (10) | −0.0160 (10) | 0.0037 (9) | −0.0113 (8) |
O24 | 0.0676 (14) | 0.124 (2) | 0.0680 (14) | −0.0247 (14) | 0.0139 (12) | −0.0354 (14) |
O25 | 0.165 (3) | 0.0495 (13) | 0.0740 (16) | −0.0125 (15) | −0.0038 (18) | −0.0060 (12) |
O26 | 0.135 (3) | 0.0565 (16) | 0.171 (3) | 0.0045 (17) | 0.036 (2) | −0.0219 (18) |
N22 | 0.0792 (18) | 0.085 (2) | 0.0506 (14) | −0.0405 (16) | 0.0013 (13) | −0.0016 (13) |
N23 | 0.0701 (16) | 0.0466 (14) | 0.084 (2) | −0.0138 (13) | −0.0136 (14) | −0.0209 (13) |
C1 | 0.103 (3) | 0.087 (3) | 0.062 (2) | −0.022 (2) | 0.0102 (19) | −0.0068 (19) |
C2 | 0.201 (6) | 0.094 (3) | 0.068 (3) | −0.065 (4) | 0.000 (3) | −0.015 (2) |
C3 | 0.175 (6) | 0.149 (5) | 0.083 (3) | −0.113 (5) | −0.031 (4) | 0.009 (3) |
C4 | 0.085 (3) | 0.156 (5) | 0.099 (3) | −0.057 (3) | −0.020 (2) | 0.014 (3) |
C5 | 0.081 (2) | 0.089 (3) | 0.069 (2) | −0.025 (2) | −0.0016 (18) | −0.0021 (18) |
C6 | 0.071 (2) | 0.078 (2) | 0.0367 (14) | −0.0313 (17) | −0.0043 (13) | 0.0037 (14) |
C7 | 0.104 (3) | 0.126 (3) | 0.0500 (18) | −0.070 (3) | −0.0088 (18) | 0.0084 (19) |
C8 | 0.0524 (17) | 0.088 (2) | 0.0523 (17) | −0.0299 (17) | −0.0051 (14) | −0.0172 (16) |
C9 | 0.0577 (16) | 0.0545 (15) | 0.0455 (14) | −0.0160 (13) | −0.0042 (12) | −0.0152 (12) |
C10 | 0.0467 (14) | 0.0546 (15) | 0.0455 (14) | −0.0130 (12) | 0.0004 (11) | −0.0192 (12) |
C11 | 0.0501 (15) | 0.0574 (17) | 0.0684 (18) | −0.0065 (13) | −0.0058 (13) | −0.0256 (14) |
C12 | 0.077 (2) | 0.0560 (18) | 0.100 (3) | −0.0164 (16) | −0.0095 (19) | −0.0330 (17) |
C13 | 0.075 (2) | 0.079 (2) | 0.088 (2) | −0.0344 (19) | −0.0033 (18) | −0.0341 (19) |
C14 | 0.0490 (16) | 0.098 (3) | 0.0607 (18) | −0.0223 (17) | −0.0044 (14) | −0.0242 (17) |
C15 | 0.0513 (15) | 0.0632 (17) | 0.0507 (15) | −0.0112 (14) | −0.0016 (12) | −0.0142 (13) |
C16 | 0.0512 (14) | 0.0500 (14) | 0.0443 (14) | −0.0208 (12) | −0.0049 (11) | −0.0148 (11) |
C17 | 0.0654 (17) | 0.0504 (15) | 0.0479 (15) | −0.0143 (13) | −0.0077 (13) | −0.0114 (12) |
C18 | 0.0674 (19) | 0.071 (2) | 0.0466 (16) | −0.0188 (16) | −0.0079 (14) | −0.0045 (14) |
C19 | 0.0681 (19) | 0.094 (3) | 0.0481 (16) | −0.0191 (18) | −0.0003 (14) | −0.0220 (17) |
C20 | 0.0556 (17) | 0.075 (2) | 0.0663 (19) | −0.0107 (15) | −0.0044 (14) | −0.0361 (16) |
C21 | 0.0486 (14) | 0.0482 (14) | 0.0561 (16) | −0.0161 (12) | −0.0107 (12) | −0.0165 (12) |
Br27—C11 | 1.903 (3) | C8—C9 | 1.538 (4) |
O2—C16 | 1.354 (3) | C9—C10 | 1.504 (4) |
O2—C9 | 1.439 (3) | C9—H9 | 0.9800 |
O24—C8 | 1.218 (4) | C10—C15 | 1.386 (4) |
O25—N23 | 1.209 (4) | C10—C11 | 1.388 (4) |
O26—N23 | 1.203 (4) | C11—C12 | 1.384 (4) |
N22—C8 | 1.331 (4) | C12—C13 | 1.357 (5) |
N22—C7 | 1.473 (4) | C12—H12 | 0.9300 |
N22—H22 | 0.8600 | C13—C14 | 1.370 (5) |
N23—C21 | 1.461 (4) | C13—H13 | 0.9300 |
C1—C6 | 1.358 (5) | C14—C15 | 1.387 (4) |
C1—C2 | 1.406 (7) | C14—H14 | 0.9300 |
C1—H1 | 0.9300 | C15—H15 | 0.9300 |
C2—C3 | 1.361 (8) | C16—C17 | 1.391 (4) |
C2—H2 | 0.9300 | C16—C21 | 1.391 (4) |
C3—C4 | 1.341 (8) | C17—C18 | 1.371 (4) |
C3—H3 | 0.9300 | C17—H17 | 0.9300 |
C4—C5 | 1.367 (6) | C18—C19 | 1.375 (5) |
C4—H4 | 0.9300 | C18—H18 | 0.9300 |
C5—C6 | 1.372 (5) | C19—C20 | 1.367 (5) |
C5—H5 | 0.9300 | C19—H19 | 0.9300 |
C6—C7 | 1.494 (5) | C20—C21 | 1.386 (4) |
C7—H7B | 0.9700 | C20—H20 | 0.9300 |
C7—H7A | 0.9700 | ||
C16—O2—C9 | 121.1 (2) | C10—C9—H9 | 109.5 |
C8—N22—C7 | 122.8 (3) | C8—C9—H9 | 109.5 |
C8—N22—H22 | 118.6 | C15—C10—C11 | 117.2 (3) |
C7—N22—H22 | 118.6 | C15—C10—C9 | 119.1 (3) |
O26—N23—O25 | 120.9 (3) | C11—C10—C9 | 123.7 (2) |
O26—N23—C21 | 118.1 (3) | C12—C11—C10 | 121.3 (3) |
O25—N23—C21 | 120.9 (3) | C12—C11—Br27 | 117.6 (2) |
C6—C1—C2 | 120.0 (4) | C10—C11—Br27 | 121.0 (2) |
C6—C1—H1 | 120.0 | C13—C12—C11 | 120.1 (3) |
C2—C1—H1 | 120.0 | C13—C12—H12 | 120.0 |
C3—C2—C1 | 118.7 (5) | C11—C12—H12 | 120.0 |
C3—C2—H2 | 120.7 | C12—C13—C14 | 120.4 (3) |
C1—C2—H2 | 120.7 | C12—C13—H13 | 119.8 |
C4—C3—C2 | 121.5 (5) | C14—C13—H13 | 119.8 |
C4—C3—H3 | 119.3 | C13—C14—C15 | 119.5 (3) |
C2—C3—H3 | 119.3 | C13—C14—H14 | 120.2 |
C3—C4—C5 | 119.6 (5) | C15—C14—H14 | 120.2 |
C3—C4—H4 | 120.2 | C10—C15—C14 | 121.5 (3) |
C5—C4—H4 | 120.2 | C10—C15—H15 | 119.3 |
C4—C5—C6 | 121.1 (5) | C14—C15—H15 | 119.3 |
C4—C5—H5 | 119.4 | O2—C16—C17 | 123.9 (2) |
C6—C5—H5 | 119.4 | O2—C16—C21 | 117.9 (2) |
C1—C6—C5 | 119.1 (4) | C17—C16—C21 | 118.2 (2) |
C1—C6—C7 | 121.0 (4) | C18—C17—C16 | 120.2 (3) |
C5—C6—C7 | 119.9 (4) | C18—C17—H17 | 119.9 |
N22—C7—C6 | 111.5 (3) | C16—C17—H17 | 119.9 |
N22—C7—H7B | 109.3 | C17—C18—C19 | 121.2 (3) |
C6—C7—H7B | 109.3 | C17—C18—H18 | 119.4 |
N22—C7—H7A | 109.3 | C19—C18—H18 | 119.4 |
C6—C7—H7A | 109.3 | C20—C19—C18 | 119.5 (3) |
H7B—C7—H7A | 108.0 | C20—C19—H19 | 120.2 |
O24—C8—N22 | 125.8 (3) | C18—C19—H19 | 120.2 |
O24—C8—C9 | 118.7 (3) | C19—C20—C21 | 120.0 (3) |
N22—C8—C9 | 115.5 (3) | C19—C20—H20 | 120.0 |
O2—C9—C10 | 111.1 (2) | C21—C20—H20 | 120.0 |
O2—C9—C8 | 106.1 (2) | C20—C21—C16 | 120.9 (3) |
C10—C9—C8 | 111.0 (2) | C20—C21—N23 | 117.2 (3) |
O2—C9—H9 | 109.5 | C16—C21—N23 | 121.9 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N22—H22···O2 | 0.86 | 2.08 | 2.521 (3) | 111 |
N22—H22···O25 | 0.86 | 2.39 | 3.227 (4) | 164 |
Experimental details
Crystal data | |
Chemical formula | C21H17BrN2O4 |
Mr | 441.28 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 7.5818 (5), 10.4650 (7), 13.1095 (10) |
α, β, γ (°) | 73.939 (6), 82.878 (6), 74.447 (6) |
V (Å3) | 961.56 (12) |
Z | 2 |
Radiation type | Cu Kα |
µ (mm−1) | 3.17 |
Crystal size (mm) | 0.38 × 0.26 × 0.18 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur Atlas Gemini ultra |
Absorption correction | Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009) |
Tmin, Tmax | 0.427, 0.565 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7135, 3363, 2522 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.105, 1.03 |
No. of reflections | 3363 |
No. of parameters | 254 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.37, −0.39 |
Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N22—H22···O2 | 0.86 | 2.08 | 2.521 (3) | 111 |
N22—H22···O25 | 0.86 | 2.39 | 3.227 (4) | 164 |
Acknowledgements
This work was supported by a research grant from the Natural Science Foundation of China (grant No. 20672092). Professor Wei-Min Dai is thanked for his valuable suggestions on this work. Mr Jiyong Liu of the X-ray crystallography facility of Zhejiang University is acknowledged for his assistance with the crystal structural analysis.
References
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The title compound, C21H17BrN2O4, is a 2-phenoxy-2-phenyl-acetamide derivative, which have been reported to deliver various biological activities such as acting as inhibitors of the coagulation factors Xa and IXa and are therefore used for the therapy of thromboembolic disorder and as safe and effective anticoagulants for myocardial infarction and ischemic disease (Dorsch, et al.; 2002, Wang et al., 2010). They are also active as glucokinase activators rendering their use for the treatment of type I and type II diabetes (Lau, et al.; 2003).
The title compound has recently been obtained during the Lewis base-catalyzed phenol-Passerini three-component reaction (phenol-P-3CR) from nitrophenols, aryl aldehydes and alkyl isocyanides (Dai & Li; 2007). We report here its crystal structure. In the molecular structure (Fig. 1), there is one benzyl group linked to the amide nitrogen atom. In addition, one 2-bromobenzene and a 2-nitrophenoxy substituents are attached to the α-carbon. The nitro-substituted benzene moiety is coplanar with the plane formed by atoms H22-N22-C8-C9-O2 due to intramolecular hydrogen bond interactions between N22-H22···O2 and N22-H22···O25.