Acta Cryst. (2009). E65, o1043 [ doi:10.1107/S1600536809013002 ]
The complete molecule of the title compound, C26H20N2O3, is generated by crystallographic twofold symmetry, with the central O atom lying on the rotation axis. The conformation is stabilized by an intramolecular N-H
O hydrogen bond. The dihedral angle between the inner and outer aromatic ring planes is 61.12 (5)°.
The title compound was prepared according to the reported procedure of Martín et al. (2006) and Wiklund et al. (2004). Colourless chunks of (I) were obtained by recrystallization from ethyl acetate.
The N-bound N atom was located in a difference map and its position and Uiso value were freely refined. The C-bound H atoms were placed in calculated positions with C—H = 0.95 Å and refined as riding with Uiso(H) = 1.2Ueq(C).
Data collection: RAPID-AUTO (Rigaku/MSC, 2004); cell refinement: RAPID-AUTO (Rigaku/MSC, 2004); data reduction: RAPID-AUTO (Rigaku/MSC, 2004); 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 (Sheldrick, 2008).
![[Figure 1]](./hb2927fig1thm.gif)
| Fig. 1. The molecular structure of (I) showing 50% probability displacement ellipsoids for the non-hydrogen atoms. Symmetry code: (i) –x, y, 1/2–y. |
| C26H20N2O3 | F(000) = 856 |
| Mr = 408.44 | Dx = 1.358 Mg m−3 |
| Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -C 2yc | Cell parameters from 3250 reflections |
| a = 9.090 (3) Å | θ = 3.4–27.5° |
| b = 21.056 (6) Å | µ = 0.09 mm−1 |
| c = 10.623 (3) Å | T = 93 K |
| β = 100.594 (3)° | Chunk, colourless |
| V = 1998.5 (10) Å3 | 0.33 × 0.30 × 0.18 mm |
| Z = 4 |
| Rigaku Spider diffractometer | 2000 reflections with I > 2σ(I) |
| Radiation source: Rotating Anode | Rint = 0.023 |
| graphite | θmax = 27.5°, θmin = 3.4° |
| ω scans | h = −11→11 |
| 8102 measured reflections | k = −27→27 |
| 2275 independent reflections | l = −10→13 |
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.111 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.00 | w = 1/[σ2(Fo2) + (0.0706P)2 + 0.28P] where P = (Fo2 + 2Fc2)/3 |
| 2275 reflections | (Δ/σ)max < 0.001 |
| 145 parameters | Δρmax = 0.25 e Å−3 |
| 0 restraints | Δρmin = −0.20 e Å−3 |
| C26H20N2O3 | V = 1998.5 (10) Å3 |
| Mr = 408.44 | Z = 4 |
| Monoclinic, C2/c | Mo Kα radiation |
| a = 9.090 (3) Å | µ = 0.09 mm−1 |
| b = 21.056 (6) Å | T = 93 K |
| c = 10.623 (3) Å | 0.33 × 0.30 × 0.18 mm |
| β = 100.594 (3)° |
| Rigaku Spider diffractometer | Rint = 0.023 |
| 8102 measured reflections | θmax = 27.5° |
| 2275 independent reflections | Standard reflections: 0 |
| 2000 reflections with I > 2σ(I) |
| R[F2 > 2σ(F2)] = 0.039 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.111 | Δρmax = 0.25 e Å−3 |
| S = 1.00 | Δρmin = −0.20 e Å−3 |
| 2275 reflections | Absolute structure: ? |
| 145 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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. |
| x | y | z | Uiso*/Ueq | ||
| O1 | 0.11910 (9) | 0.38137 (4) | 0.34545 (8) | 0.0229 (2) | |
| O2 | 0.0000 | 0.29421 (5) | 0.2500 | 0.0225 (3) | |
| N1 | 0.41159 (11) | 0.37188 (5) | 0.43582 (9) | 0.0204 (2) | |
| C1 | 0.56426 (13) | 0.43835 (6) | 0.59357 (11) | 0.0236 (3) | |
| H1 | 0.4845 | 0.4399 | 0.6401 | 0.028* | |
| C2 | 0.69505 (14) | 0.47174 (6) | 0.63703 (12) | 0.0275 (3) | |
| H2 | 0.7045 | 0.4964 | 0.7130 | 0.033* | |
| C3 | 0.81191 (14) | 0.46930 (6) | 0.57006 (13) | 0.0274 (3) | |
| H3 | 0.9020 | 0.4918 | 0.6006 | 0.033* | |
| C4 | 0.79712 (13) | 0.43398 (5) | 0.45834 (12) | 0.0246 (3) | |
| H4 | 0.8771 | 0.4324 | 0.4121 | 0.030* | |
| C5 | 0.66575 (13) | 0.40089 (5) | 0.41392 (11) | 0.0215 (3) | |
| H5 | 0.6555 | 0.3771 | 0.3369 | 0.026* | |
| C6 | 0.54946 (12) | 0.40262 (5) | 0.48214 (11) | 0.0185 (3) | |
| C7 | 0.39399 (12) | 0.30870 (5) | 0.40566 (10) | 0.0176 (2) | |
| C8 | 0.51448 (12) | 0.26579 (6) | 0.43627 (11) | 0.0207 (3) | |
| H8 | 0.6099 | 0.2811 | 0.4764 | 0.025* | |
| C9 | 0.49596 (13) | 0.20234 (6) | 0.40898 (11) | 0.0233 (3) | |
| H9 | 0.5787 | 0.1744 | 0.4313 | 0.028* | |
| C10 | 0.35825 (13) | 0.17796 (6) | 0.34912 (11) | 0.0234 (3) | |
| H10 | 0.3469 | 0.1339 | 0.3305 | 0.028* | |
| C11 | 0.23933 (13) | 0.21874 (5) | 0.31759 (11) | 0.0206 (3) | |
| H11 | 0.1453 | 0.2025 | 0.2763 | 0.025* | |
| C12 | 0.25345 (12) | 0.28396 (5) | 0.34495 (10) | 0.0179 (3) | |
| C13 | 0.12427 (12) | 0.32625 (5) | 0.31547 (10) | 0.0183 (2) | |
| H1N | 0.3269 (17) | 0.3947 (7) | 0.4330 (15) | 0.039 (4)* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0191 (4) | 0.0209 (4) | 0.0273 (5) | 0.0013 (3) | 0.0006 (3) | −0.0033 (3) |
| O2 | 0.0175 (6) | 0.0198 (6) | 0.0272 (6) | 0.000 | −0.0037 (5) | 0.000 |
| N1 | 0.0157 (5) | 0.0197 (5) | 0.0248 (5) | 0.0012 (4) | 0.0014 (4) | −0.0022 (4) |
| C1 | 0.0231 (6) | 0.0258 (6) | 0.0215 (6) | 0.0022 (5) | 0.0033 (5) | −0.0004 (5) |
| C2 | 0.0299 (7) | 0.0248 (6) | 0.0244 (6) | 0.0003 (5) | −0.0037 (5) | −0.0046 (5) |
| C3 | 0.0219 (6) | 0.0198 (6) | 0.0367 (7) | −0.0020 (4) | −0.0045 (5) | 0.0005 (5) |
| C4 | 0.0199 (6) | 0.0200 (6) | 0.0340 (7) | 0.0010 (4) | 0.0051 (5) | 0.0036 (5) |
| C5 | 0.0225 (6) | 0.0199 (6) | 0.0215 (6) | 0.0012 (4) | 0.0027 (5) | −0.0015 (4) |
| C6 | 0.0171 (6) | 0.0170 (5) | 0.0197 (5) | 0.0008 (4) | −0.0009 (4) | 0.0014 (4) |
| C7 | 0.0181 (6) | 0.0189 (5) | 0.0158 (5) | −0.0003 (4) | 0.0033 (4) | 0.0015 (4) |
| C8 | 0.0170 (6) | 0.0234 (6) | 0.0212 (6) | 0.0002 (4) | 0.0019 (4) | 0.0035 (4) |
| C9 | 0.0218 (6) | 0.0230 (6) | 0.0256 (6) | 0.0058 (4) | 0.0059 (5) | 0.0055 (5) |
| C10 | 0.0260 (6) | 0.0179 (5) | 0.0268 (6) | 0.0004 (5) | 0.0064 (5) | 0.0007 (5) |
| C11 | 0.0206 (6) | 0.0210 (6) | 0.0203 (6) | −0.0019 (4) | 0.0039 (4) | 0.0002 (4) |
| C12 | 0.0181 (6) | 0.0202 (6) | 0.0157 (5) | 0.0005 (4) | 0.0037 (4) | 0.0014 (4) |
| C13 | 0.0173 (6) | 0.0197 (5) | 0.0175 (5) | −0.0021 (4) | 0.0023 (4) | 0.0002 (4) |
| O1—C13 | 1.2067 (14) | C4—H4 | 0.9500 |
| O2—C13i | 1.3877 (12) | C5—C6 | 1.3876 (17) |
| O2—C13 | 1.3877 (12) | C5—H5 | 0.9500 |
| N1—C7 | 1.3708 (15) | C7—C8 | 1.4109 (15) |
| N1—C6 | 1.4159 (14) | C7—C12 | 1.4199 (15) |
| N1—H1N | 0.903 (16) | C8—C9 | 1.3708 (17) |
| C1—C2 | 1.3853 (18) | C8—H8 | 0.9500 |
| C1—C6 | 1.3880 (16) | C9—C10 | 1.3936 (17) |
| C1—H1 | 0.9500 | C9—H9 | 0.9500 |
| C2—C3 | 1.3838 (19) | C10—C11 | 1.3728 (16) |
| C2—H2 | 0.9500 | C10—H10 | 0.9500 |
| C3—C4 | 1.3860 (18) | C11—C12 | 1.4047 (15) |
| C3—H3 | 0.9500 | C11—H11 | 0.9500 |
| C4—C5 | 1.3881 (16) | C12—C13 | 1.4610 (15) |
| C13i—O2—C13 | 121.84 (12) | N1—C7—C8 | 121.02 (10) |
| C7—N1—C6 | 125.64 (9) | N1—C7—C12 | 121.25 (10) |
| C7—N1—H1N | 116.5 (10) | C8—C7—C12 | 117.72 (10) |
| C6—N1—H1N | 117.6 (10) | C9—C8—C7 | 121.02 (10) |
| C2—C1—C6 | 120.13 (11) | C9—C8—H8 | 119.5 |
| C2—C1—H1 | 119.9 | C7—C8—H8 | 119.5 |
| C6—C1—H1 | 119.9 | C8—C9—C10 | 121.37 (11) |
| C3—C2—C1 | 120.18 (11) | C8—C9—H9 | 119.3 |
| C3—C2—H2 | 119.9 | C10—C9—H9 | 119.3 |
| C1—C2—H2 | 119.9 | C11—C10—C9 | 118.80 (11) |
| C2—C3—C4 | 119.82 (11) | C11—C10—H10 | 120.6 |
| C2—C3—H3 | 120.1 | C9—C10—H10 | 120.6 |
| C4—C3—H3 | 120.1 | C10—C11—C12 | 121.54 (11) |
| C3—C4—C5 | 120.16 (12) | C10—C11—H11 | 119.2 |
| C3—C4—H4 | 119.9 | C12—C11—H11 | 119.2 |
| C5—C4—H4 | 119.9 | C11—C12—C7 | 119.53 (10) |
| C6—C5—C4 | 119.98 (11) | C11—C12—C13 | 120.82 (10) |
| C6—C5—H5 | 120.0 | C7—C12—C13 | 119.62 (10) |
| C4—C5—H5 | 120.0 | O1—C13—O2 | 122.15 (10) |
| C5—C6—C1 | 119.73 (10) | O1—C13—C12 | 126.76 (10) |
| C5—C6—N1 | 121.13 (10) | O2—C13—C12 | 111.05 (10) |
| C1—C6—N1 | 119.01 (10) | ||
| C6—C1—C2—C3 | −0.43 (18) | C8—C9—C10—C11 | −0.18 (18) |
| C1—C2—C3—C4 | 0.82 (18) | C9—C10—C11—C12 | −0.38 (17) |
| C2—C3—C4—C5 | −0.28 (18) | C10—C11—C12—C7 | 0.54 (17) |
| C3—C4—C5—C6 | −0.66 (17) | C10—C11—C12—C13 | −177.48 (11) |
| C4—C5—C6—C1 | 1.05 (16) | N1—C7—C12—C11 | −178.92 (10) |
| C4—C5—C6—N1 | 176.88 (10) | C8—C7—C12—C11 | −0.14 (16) |
| C2—C1—C6—C5 | −0.51 (17) | N1—C7—C12—C13 | −0.87 (16) |
| C2—C1—C6—N1 | −176.42 (10) | C8—C7—C12—C13 | 177.90 (10) |
| C7—N1—C6—C5 | 56.75 (16) | C13i—O2—C13—O1 | 18.14 (8) |
| C7—N1—C6—C1 | −127.39 (12) | C13i—O2—C13—C12 | −164.03 (10) |
| C6—N1—C7—C8 | 9.20 (17) | C11—C12—C13—O1 | 172.29 (11) |
| C6—N1—C7—C12 | −172.07 (10) | C7—C12—C13—O1 | −5.73 (18) |
| N1—C7—C8—C9 | 178.37 (10) | C11—C12—C13—O2 | −5.43 (14) |
| C12—C7—C8—C9 | −0.41 (17) | C7—C12—C13—O2 | 176.56 (9) |
| C7—C8—C9—C10 | 0.58 (18) |
| Symmetry codes: (i) −x, y, −z+1/2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1N···O1 | 0.903 (16) | 1.966 (15) | 2.6629 (14) | 132.7 (13) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1N···O1 | 0.903 (16) | 1.966 (15) | 2.6629 (14) | 132.7 (13) |
The authors thank the Scientific Researching Fund Projects of China West Normal University (grant No. 06B003) and the Youth Fund Projects of Sichuan Educational Department (grant No. 2006B039).
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Huelgas, G., Quintero, L., Anaya de Parrodi, C. & Bernès, S. (2006). Acta Cryst. E62, o3191–o3192.
Martín, A., Mesa, M., Docampo, M. L., Gómez, V. & Pellón, R. F. (2006). Synth. Commun. 36, 271–277.
Rigaku/MSC (2004). RAPID-AUTO. Rigaku/MSC Inc., The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Wiklund, P., Evans, M. R. & Bergman, J. (2004). J. Org. Chem. 69, 6371–6376.
N-Phenylanthranilic acid derivatives display a antipyretic acitivity, its RhI complex is known as a remarkably active hydrogenation catalyst. N-phenyl anthranilic acid anhydride, which is considered as an important reaction intermediate, We here report the crystal structure of the title compound, (I).
Bond lengths and angles in (I) (Fig. 1) are within their normal ranges. In each independent molecule, the arrangement of N—H···O hydrogen bond and the planar (O=C—O) group is almost coplanar with respect to its carrier benzene ring, with dihedral angle of 6.63 (1)°, but the two benzene rings in the diphenylamine units are twisted with a dihedral angle of 61.12 (4)°. The structure is stabilized by an intramolecular hydrogen bond from an H atom of a amido N atom to a carbonyl O atom on the six-membered ring.