Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807050039/rk2049sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807050039/rk2049Isup2.hkl |
CCDC reference: 667368
Spiroadduct (3a) was synthesized by the procedure described in (Roussel et al., 2003). Synthesis of (4): to a solution of spiroheterocycle (3a) (0.64 mmol) in the minimum volume of acetone (3 ml) was added activated zinc dust (61.18 mmol). To the resulting suspension was slowly added 3M HCl (52.5 ml). The mixture was then stirred for 2 h at room temperature. The zinc was filtered off and rinsed with 3 M HCl and CHCl3. To this mixture, while vigorously stirring, solid K2CO3 was slowly added until pH = 7. After stirring for two additional hours, the organic layer was separated, dried with Na2SO4, filtered and concentrated to give the product as a solid, which was recrystallized from CH2Cl2.
All H atoms attached to C atoms and N atom were fixed geometrically and treated as riding with C–H = 0.95 Å (aromatic), 0.99 Å (methylene), 1.00 Å (methine) and N–H = 0.88 Å with Uiso(H) = 1.2Ueq(C or N).
We previously reported that 1,3-dipolar cycloaddition of C,N-diphenylnitrone (1) to 3-methylenephtalide (2) produced a mixture of diastereoisomers (Roussel et al., 2003). The molecular structure of the major cycloadduct (3a) was confirmed by single-crystal X-ray diffraction (Daran et al., 2006) (Fig. 1).
In a previous paper (Laghrib et al., 2007), we described the evolution of isoxazolidines obtained by cycloaddition of C-tolyl-N-phenylnitrone with Tulipalin A in Zn / HCl media. The reduction of the nitrogen-oxygen bond of the heterocycle led to a functionalized γ-lactam. This reduction process has been successfully applied for the preparation of biologically active compounds (Goti et al., 1997; Padwa et al., 1981; Jung & Vu, 1996). We report here, on the evolution of major spiroadduct (3a) treated with Zn / 3M HCl. The reaction did not stop at the formation of aminoalcohol but was followed by dehydratation and hydrogenation to give (4) (Fig.2).
1H and 13C NMR studies of (4) did not provide much information on the structural behaviour of this product, therefore, we conducted single-crystal X-ray diffraction studies to get detailed information of the stereochemistry of (4).
The title compound (4) is built up from a phtalide fragment connected to a 2-N-phenyl-2-phenylethyl moiety (Fig. 2). The structural anlysis shows that compound (4) is the (SR/RS) diastereoisomer. The phtalide group is planar as expected with the largest deviation from the mean plane being 0.030 (2) Å at C41. It makes a dihedral angle of 51.37 (6)° with the N-phenyl group and 81.06 (6)° with the benzene ring. The benzene and the N-phenyl rings are nearly perpendicular with a dihedral angle of 80.01 (7)°. The occurrence of weak N–H···O and C–H···O hydrogen bonding interactions (see Table) help in stabilizing the packing.
For related structures, see: Daran et al. (2006); Laghrib et al. (2007). For related literature, see: Goti et al. (1997); Jung & Vu (1996); Padwa et al. (1981); Roussel et al. (2003).
Data collection: IPDS (Stoe, 2000); cell refinement: IPDS (Stoe, 2000); data reduction: X-RED (Stoe, 1996); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C22H19NO2 | Z = 2 |
Mr = 329.38 | F(000) = 348 |
Triclinic, P1 | Dx = 1.281 Mg m−3 |
a = 6.303 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 7.774 (2) Å | Cell parameters from 1428 reflections |
c = 17.466 (5) Å | θ = 2.2–26.2° |
α = 88.15 (3)° | µ = 0.08 mm−1 |
β = 88.99 (4)° | T = 180 K |
γ = 86.62 (4)° | Plate, colourless |
V = 853.8 (4) Å3 | 0.28 × 0.14 × 0.06 mm |
Stoe IPDS diffractometer | 1706 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.064 |
Graphite monochromator | θmax = 25.0°, θmin = 2.3° |
φ scans | h = −7→7 |
7801 measured reflections | k = −9→9 |
2852 independent reflections | l = −20→20 |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.083 | H-atom parameters constrained |
S = 0.81 | w = 1/[σ2(Fo2) + (0.0408P)2 where P = (Fo2 + 2Fc2)/3 |
2852 reflections | (Δ/σ)max = 0.001 |
226 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
C22H19NO2 | γ = 86.62 (4)° |
Mr = 329.38 | V = 853.8 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.303 (2) Å | Mo Kα radiation |
b = 7.774 (2) Å | µ = 0.08 mm−1 |
c = 17.466 (5) Å | T = 180 K |
α = 88.15 (3)° | 0.28 × 0.14 × 0.06 mm |
β = 88.99 (4)° |
Stoe IPDS diffractometer | 1706 reflections with I > 2σ(I) |
7801 measured reflections | Rint = 0.064 |
2852 independent reflections |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.083 | H-atom parameters constrained |
S = 0.81 | Δρmax = 0.16 e Å−3 |
2852 reflections | Δρmin = −0.16 e Å−3 |
226 parameters |
Experimental. The data were collected on a Stoe Imaging Plate Diffraction System (IPDS). The crystal-to-detector distance was 70 mm. 167 frames (3 min per frame) were obtained with 0 < φ < 250.5° and with the crystals rotated through 1.5° in φ. Coverage of the unique set was over 93.5% complete to at least 26.08°. Crystal decay was monitored by measuring 200 reflections per frame. The Stoe IPDS because of the fixed phi spindle does not allow easy access to the cusp of data along the mount axis which explains why the _diffrn_measured_fraction_theta_full is low, 0.94. This is an instrumentation-based restriction, which the authors have little control over. |
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 > 2σ(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 | ||
C1 | 0.6495 (3) | 0.8355 (2) | 0.27286 (9) | 0.0254 (4) | |
H1 | 0.5358 | 0.9230 | 0.2560 | 0.030* | |
C2 | 0.6137 (3) | 0.6640 (2) | 0.23486 (9) | 0.0272 (4) | |
H2A | 0.7379 | 0.5834 | 0.2456 | 0.033* | |
H2B | 0.4879 | 0.6140 | 0.2596 | 0.033* | |
C3 | 0.5806 (3) | 0.6733 (2) | 0.14912 (9) | 0.0247 (4) | |
H3 | 0.7025 | 0.7274 | 0.1223 | 0.030* | |
C4 | 0.2424 (3) | 0.6721 (3) | 0.09876 (9) | 0.0289 (5) | |
C31 | 0.5482 (3) | 0.4991 (2) | 0.11756 (9) | 0.0239 (4) | |
C41 | 0.3477 (3) | 0.5016 (2) | 0.08731 (9) | 0.0248 (4) | |
C51 | 0.2692 (3) | 0.3550 (3) | 0.05605 (9) | 0.0321 (5) | |
H51 | 0.1308 | 0.3573 | 0.0352 | 0.039* | |
C61 | 0.4010 (4) | 0.2075 (3) | 0.05679 (10) | 0.0387 (5) | |
H61 | 0.3534 | 0.1060 | 0.0354 | 0.046* | |
C71 | 0.6024 (4) | 0.2038 (3) | 0.08808 (10) | 0.0392 (5) | |
H71 | 0.6887 | 0.0994 | 0.0886 | 0.047* | |
C81 | 0.6799 (3) | 0.3501 (3) | 0.11865 (9) | 0.0322 (5) | |
H81 | 0.8181 | 0.3479 | 0.1395 | 0.039* | |
C111 | 0.9257 (3) | 1.0536 (2) | 0.26694 (9) | 0.0241 (4) | |
C112 | 1.1168 (3) | 1.1053 (2) | 0.23592 (9) | 0.0273 (4) | |
H112 | 1.1921 | 1.0348 | 0.1999 | 0.033* | |
C113 | 1.1997 (3) | 1.2580 (3) | 0.25650 (10) | 0.0310 (5) | |
H113 | 1.3323 | 1.2898 | 0.2355 | 0.037* | |
C114 | 1.0895 (3) | 1.3644 (2) | 0.30772 (10) | 0.0321 (5) | |
H114 | 1.1458 | 1.4692 | 0.3220 | 0.039* | |
C115 | 0.8979 (3) | 1.3164 (2) | 0.33753 (9) | 0.0303 (5) | |
H115 | 0.8216 | 1.3893 | 0.3724 | 0.036* | |
C116 | 0.8137 (3) | 1.1633 (2) | 0.31757 (9) | 0.0274 (4) | |
H116 | 0.6801 | 1.1329 | 0.3383 | 0.033* | |
C121 | 0.6298 (3) | 0.8057 (2) | 0.35941 (9) | 0.0265 (4) | |
C122 | 0.8025 (3) | 0.7506 (2) | 0.40326 (9) | 0.0321 (5) | |
H122 | 0.9399 | 0.7382 | 0.3802 | 0.039* | |
C123 | 0.7758 (4) | 0.7132 (3) | 0.48085 (10) | 0.0406 (5) | |
H123 | 0.8948 | 0.6733 | 0.5105 | 0.049* | |
C124 | 0.5789 (4) | 0.7336 (3) | 0.51517 (11) | 0.0451 (6) | |
H124 | 0.5615 | 0.7079 | 0.5684 | 0.054* | |
C125 | 0.4071 (4) | 0.7910 (3) | 0.47233 (11) | 0.0486 (6) | |
H125 | 0.2707 | 0.8059 | 0.4960 | 0.058* | |
C126 | 0.4324 (3) | 0.8273 (3) | 0.39477 (10) | 0.0385 (5) | |
H126 | 0.3128 | 0.8674 | 0.3655 | 0.046* | |
N1 | 0.8532 (2) | 0.8946 (2) | 0.24813 (8) | 0.0309 (4) | |
H1A | 0.9361 | 0.8266 | 0.2197 | 0.037* | |
O1 | 0.38175 (19) | 0.77239 (16) | 0.13285 (6) | 0.0298 (3) | |
O2 | 0.0643 (2) | 0.72846 (19) | 0.08469 (7) | 0.0448 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0253 (10) | 0.0290 (11) | 0.0227 (9) | −0.0062 (9) | −0.0024 (7) | −0.0033 (8) |
C2 | 0.0311 (11) | 0.0294 (11) | 0.0216 (8) | −0.0062 (9) | −0.0027 (7) | −0.0021 (8) |
C3 | 0.0195 (10) | 0.0293 (11) | 0.0253 (9) | −0.0010 (9) | −0.0016 (7) | 0.0001 (8) |
C4 | 0.0252 (11) | 0.0414 (13) | 0.0204 (9) | −0.0025 (10) | −0.0013 (8) | −0.0063 (8) |
C31 | 0.0259 (10) | 0.0278 (11) | 0.0183 (8) | −0.0038 (9) | 0.0020 (7) | −0.0031 (7) |
C41 | 0.0262 (10) | 0.0316 (11) | 0.0174 (8) | −0.0065 (9) | 0.0027 (7) | −0.0048 (8) |
C51 | 0.0339 (11) | 0.0409 (13) | 0.0231 (9) | −0.0140 (11) | 0.0011 (8) | −0.0058 (9) |
C61 | 0.0602 (15) | 0.0329 (13) | 0.0246 (10) | −0.0137 (12) | 0.0026 (9) | −0.0080 (9) |
C71 | 0.0592 (15) | 0.0280 (12) | 0.0299 (10) | 0.0027 (11) | 0.0035 (10) | −0.0049 (9) |
C81 | 0.0341 (12) | 0.0355 (12) | 0.0265 (10) | 0.0010 (10) | 0.0000 (8) | −0.0019 (8) |
C111 | 0.0251 (10) | 0.0264 (11) | 0.0209 (9) | −0.0028 (9) | −0.0030 (7) | 0.0003 (8) |
C112 | 0.0268 (11) | 0.0296 (11) | 0.0255 (9) | −0.0019 (9) | 0.0015 (8) | −0.0006 (8) |
C113 | 0.0272 (11) | 0.0326 (12) | 0.0332 (10) | −0.0053 (10) | 0.0012 (8) | 0.0037 (9) |
C114 | 0.0409 (13) | 0.0266 (11) | 0.0298 (10) | −0.0089 (10) | −0.0034 (9) | −0.0008 (8) |
C115 | 0.0387 (12) | 0.0277 (12) | 0.0246 (9) | −0.0012 (10) | −0.0003 (8) | −0.0033 (8) |
C116 | 0.0269 (11) | 0.0308 (11) | 0.0249 (9) | −0.0039 (9) | 0.0030 (7) | −0.0038 (8) |
C121 | 0.0311 (11) | 0.0263 (11) | 0.0230 (9) | −0.0064 (9) | −0.0006 (8) | −0.0064 (8) |
C122 | 0.0328 (12) | 0.0361 (12) | 0.0279 (10) | −0.0021 (10) | −0.0027 (8) | −0.0066 (9) |
C123 | 0.0480 (14) | 0.0443 (14) | 0.0295 (10) | −0.0001 (12) | −0.0105 (9) | −0.0018 (9) |
C124 | 0.0549 (15) | 0.0545 (15) | 0.0257 (10) | −0.0036 (13) | 0.0025 (10) | 0.0005 (10) |
C125 | 0.0404 (13) | 0.0701 (17) | 0.0346 (11) | −0.0037 (13) | 0.0123 (10) | 0.0017 (11) |
C126 | 0.0268 (11) | 0.0565 (15) | 0.0322 (11) | −0.0037 (11) | 0.0001 (8) | 0.0018 (10) |
N1 | 0.0305 (9) | 0.0307 (10) | 0.0328 (8) | −0.0095 (8) | 0.0096 (7) | −0.0128 (7) |
O1 | 0.0283 (7) | 0.0317 (8) | 0.0298 (7) | 0.0007 (6) | −0.0061 (5) | −0.0077 (6) |
O2 | 0.0276 (8) | 0.0636 (11) | 0.0433 (8) | 0.0077 (8) | −0.0087 (6) | −0.0151 (7) |
C1—N1 | 1.443 (2) | C111—N1 | 1.393 (2) |
C1—C121 | 1.526 (2) | C111—C116 | 1.401 (2) |
C1—C2 | 1.539 (2) | C112—C113 | 1.385 (3) |
C1—H1 | 1.0000 | C112—H112 | 0.9500 |
C2—C3 | 1.514 (2) | C113—C114 | 1.388 (2) |
C2—H2A | 0.9900 | C113—H113 | 0.9500 |
C2—H2B | 0.9900 | C114—C115 | 1.374 (3) |
C3—O1 | 1.459 (2) | C114—H114 | 0.9500 |
C3—C31 | 1.505 (2) | C115—C116 | 1.389 (3) |
C3—H3 | 1.0000 | C115—H115 | 0.9500 |
C4—O2 | 1.207 (2) | C116—H116 | 0.9500 |
C4—O1 | 1.365 (2) | C121—C122 | 1.381 (3) |
C4—C41 | 1.465 (3) | C121—C126 | 1.383 (3) |
C31—C41 | 1.377 (2) | C122—C123 | 1.386 (3) |
C31—C81 | 1.385 (3) | C122—H122 | 0.9500 |
C41—C51 | 1.399 (3) | C123—C124 | 1.372 (3) |
C51—C61 | 1.376 (3) | C123—H123 | 0.9500 |
C51—H51 | 0.9500 | C124—C125 | 1.371 (3) |
C61—C71 | 1.389 (3) | C124—H124 | 0.9500 |
C61—H61 | 0.9500 | C125—C126 | 1.383 (3) |
C71—C81 | 1.389 (3) | C125—H125 | 0.9500 |
C71—H71 | 0.9500 | C126—H126 | 0.9500 |
C81—H81 | 0.9500 | N1—H1A | 0.8800 |
C111—C112 | 1.388 (3) | ||
N1—C1—C121 | 113.53 (14) | C112—C111—C116 | 118.24 (16) |
N1—C1—C2 | 109.13 (14) | N1—C111—C116 | 122.22 (16) |
C121—C1—C2 | 107.81 (16) | C113—C112—C111 | 121.20 (16) |
N1—C1—H1 | 108.8 | C113—C112—H112 | 119.4 |
C121—C1—H1 | 108.8 | C111—C112—H112 | 119.4 |
C2—C1—H1 | 108.8 | C112—C113—C114 | 120.14 (18) |
C3—C2—C1 | 116.27 (15) | C112—C113—H113 | 119.9 |
C3—C2—H2A | 108.2 | C114—C113—H113 | 119.9 |
C1—C2—H2A | 108.2 | C115—C114—C113 | 119.20 (18) |
C3—C2—H2B | 108.2 | C115—C114—H114 | 120.4 |
C1—C2—H2B | 108.2 | C113—C114—H114 | 120.4 |
H2A—C2—H2B | 107.4 | C114—C115—C116 | 121.14 (17) |
O1—C3—C31 | 103.91 (14) | C114—C115—H115 | 119.4 |
O1—C3—C2 | 109.13 (13) | C116—C115—H115 | 119.4 |
C31—C3—C2 | 112.10 (15) | C115—C116—C111 | 120.04 (17) |
O1—C3—H3 | 110.5 | C115—C116—H116 | 120.0 |
C31—C3—H3 | 110.5 | C111—C116—H116 | 120.0 |
C2—C3—H3 | 110.5 | C122—C121—C126 | 118.79 (17) |
O2—C4—O1 | 120.36 (17) | C122—C121—C1 | 121.80 (16) |
O2—C4—C41 | 131.13 (18) | C126—C121—C1 | 119.35 (16) |
O1—C4—C41 | 108.50 (15) | C121—C122—C123 | 120.20 (19) |
C41—C31—C81 | 121.00 (17) | C121—C122—H122 | 119.9 |
C41—C31—C3 | 108.59 (15) | C123—C122—H122 | 119.9 |
C81—C31—C3 | 130.33 (16) | C124—C123—C122 | 120.47 (19) |
C31—C41—C51 | 121.69 (18) | C124—C123—H123 | 119.8 |
C31—C41—C4 | 108.45 (15) | C122—C123—H123 | 119.8 |
C51—C41—C4 | 129.77 (17) | C125—C124—C123 | 119.72 (19) |
C61—C51—C41 | 117.12 (18) | C125—C124—H124 | 120.1 |
C61—C51—H51 | 121.4 | C123—C124—H124 | 120.1 |
C41—C51—H51 | 121.4 | C124—C125—C126 | 120.1 (2) |
C51—C61—C71 | 121.41 (18) | C124—C125—H125 | 120.0 |
C51—C61—H61 | 119.3 | C126—C125—H125 | 120.0 |
C71—C61—H61 | 119.3 | C125—C126—C121 | 120.71 (19) |
C61—C71—C81 | 121.17 (19) | C125—C126—H126 | 119.6 |
C61—C71—H71 | 119.4 | C121—C126—H126 | 119.6 |
C81—C71—H71 | 119.4 | C111—N1—C1 | 123.48 (14) |
C31—C81—C71 | 117.60 (18) | C111—N1—H1A | 118.3 |
C31—C81—H81 | 121.2 | C1—N1—H1A | 118.3 |
C71—C81—H81 | 121.2 | C4—O1—C3 | 110.49 (13) |
C112—C111—N1 | 119.53 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O2i | 0.88 | 2.60 | 3.390 (2) | 150 |
C3—H3···O2i | 1.00 | 2.36 | 3.279 (3) | 152 |
C51—H51···O2ii | 0.95 | 2.57 | 3.366 (2) | 141 |
Symmetry codes: (i) x+1, y, z; (ii) −x, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C22H19NO2 |
Mr | 329.38 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 180 |
a, b, c (Å) | 6.303 (2), 7.774 (2), 17.466 (5) |
α, β, γ (°) | 88.15 (3), 88.99 (4), 86.62 (4) |
V (Å3) | 853.8 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.28 × 0.14 × 0.06 |
Data collection | |
Diffractometer | Stoe IPDS |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7801, 2852, 1706 |
Rint | 0.064 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.083, 0.81 |
No. of reflections | 2852 |
No. of parameters | 226 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.16, −0.16 |
Computer programs: IPDS (Stoe, 2000), X-RED (Stoe, 1996), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O2i | 0.88 | 2.60 | 3.390 (2) | 149.5 |
C3—H3···O2i | 1.00 | 2.36 | 3.279 (3) | 151.9 |
C51—H51···O2ii | 0.95 | 2.57 | 3.366 (2) | 141.1 |
Symmetry codes: (i) x+1, y, z; (ii) −x, −y+1, −z. |
We previously reported that 1,3-dipolar cycloaddition of C,N-diphenylnitrone (1) to 3-methylenephtalide (2) produced a mixture of diastereoisomers (Roussel et al., 2003). The molecular structure of the major cycloadduct (3a) was confirmed by single-crystal X-ray diffraction (Daran et al., 2006) (Fig. 1).
In a previous paper (Laghrib et al., 2007), we described the evolution of isoxazolidines obtained by cycloaddition of C-tolyl-N-phenylnitrone with Tulipalin A in Zn / HCl media. The reduction of the nitrogen-oxygen bond of the heterocycle led to a functionalized γ-lactam. This reduction process has been successfully applied for the preparation of biologically active compounds (Goti et al., 1997; Padwa et al., 1981; Jung & Vu, 1996). We report here, on the evolution of major spiroadduct (3a) treated with Zn / 3M HCl. The reaction did not stop at the formation of aminoalcohol but was followed by dehydratation and hydrogenation to give (4) (Fig.2).
1H and 13C NMR studies of (4) did not provide much information on the structural behaviour of this product, therefore, we conducted single-crystal X-ray diffraction studies to get detailed information of the stereochemistry of (4).
The title compound (4) is built up from a phtalide fragment connected to a 2-N-phenyl-2-phenylethyl moiety (Fig. 2). The structural anlysis shows that compound (4) is the (SR/RS) diastereoisomer. The phtalide group is planar as expected with the largest deviation from the mean plane being 0.030 (2) Å at C41. It makes a dihedral angle of 51.37 (6)° with the N-phenyl group and 81.06 (6)° with the benzene ring. The benzene and the N-phenyl rings are nearly perpendicular with a dihedral angle of 80.01 (7)°. The occurrence of weak N–H···O and C–H···O hydrogen bonding interactions (see Table) help in stabilizing the packing.