Abstract
The title compound, C21H17BrN2O4, a 2-phenoxy-2-phenylacetamide derivative, exhibits a stereogenic center but crystallizes as a racemate as indicated by the centrosymmetric space group. 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
C21H17BrN2O4
M r = 441.28
Triclinic,
a = 7.5818 (5) Å
b = 10.4650 (7) Å
c = 13.1095 (10) Å
α = 73.939 (6)°
β = 82.878 (6)°
γ = 74.447 (6)°
V = 961.56 (12) Å3
Z = 2
Cu Kα radiation
μ = 3.17 mm−1
T = 293 K
0.38 × 0.26 × 0.18 mm
Data collection
Oxford Diffraction Xcalibur Atlas Gemini ultra diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.427, T max = 0.565
7135 measured reflections
3363 independent reflections
2522 reflections with I > 2σ(I)
R int = 0.030
Refinement
R[F 2 > 2σ(F 2)] = 0.038
wR(F 2) = 0.105
S = 1.03
3363 reflections
254 parameters
H-atom parameters constrained
Δρmax = 0.37 e Å−3
Δρmin = −0.39 e Å−3
Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); 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: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.
Supplementary Material
Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810014996/im2196sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S1600536810014996/im2196Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Table 1. Hydrogen-bond geometry (Å, °).
| 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 |
Acknowledgments
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.
supplementary crystallographic information
Comment
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.
Experimental
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 column chromatography (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.
Refinement
The H atoms were placed in calculated positions with C—H = 0.93-0.98 Å, and included in the refinement in riding model, with Uiso(H) = 1.2Ueq (carrier atom).
Figures
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.
Crystal data
| 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 |
Data collection
| Oxford Diffraction Xcalibur Atlas Gemini ultra diffractometer | 3363 independent reflections |
| Radiation source: fine-focus sealed tube | 2522 reflections with I > 2σ(I) |
| graphite | 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
| 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) |
Special details
| 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| 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) |
Atomic displacement parameters (Å2)
| 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) |
Geometric parameters (Å, °)
| 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) |
Hydrogen-bond geometry (Å, °)
| 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 |
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2196).
References
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810014996/im2196sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S1600536810014996/im2196Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report