1′,3′,3′-Trimethyl-2,3-diphenyl-2,3-di­hydro­isoxazole-5(4H)-spiro-2′-indoline

Laghrib, N.; Daran, J.-C.; Fihi, R.; Majidi, L.; Azrour, M.

doi:10.1107/S1600536809002062

1',3',3'-Trimethyl-2,3-diphenyl-2,3-dihydroisoxazole-5(4H)-spiro-2'-indoline

N. Laghrib, J.-C. Daran, R. Fihi, L. Majidi and M. Azrour

Two diastereoisomers of the title compound, C₂₅H₂₆N₂O, have been prepared by cycloaddition between 1,3,3-trimethyl-2-methyleneindoline and C-phenyl-N-phenylnitrone. The stereochemistry of the major diastereoisomer, viz. S,R/R,S, is confirmed by the X-ray analysis. The oxazole and the pyrole rings have envelope conformations. The packing is stabilized by weak C-H

interactions involving the phenyl ring attached to the N atom of the oxazole and the phenyl ring of the indole fragment.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536809002062/fl2228sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536809002062/fl2228Isup2.hkl Contains datablock I

CCDC reference: 722101

checkCIF report

Key indicators

Single-crystal X-ray study
T = 180 K
Mean (C-C) = 0.005 Å
R factor = 0.042
wR factor = 0.105
Data-to-parameter ratio = 7.9

checkCIF/PLATON results

No syntax errors found



Alert level C
            Value of measurement temperature given =   180.000
            Value of melting point given =     0.000
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.89
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.04
           From the CIF: _reflns_number_total               2021
           Count of symmetry unique reflns         2073
           Completeness (_total/calc)             97.49%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT792_ALERT_1_G The Model has Chirality at C1      (Verify) ....          S
PLAT792_ALERT_1_G The Model has Chirality at C9      (Verify) ....          R

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Heterocyclic spirocompounds are of interest in synthetic organic chemistry (Pariera et al., 1993; Alonso-Perarnau et al., 1997; Cacciarini et al., 2000). The cycloaddition between dipolarophiles bearing an exocyclic carbon-carbon double bond and appropriate1,3-dipoles is one of the best methods for the synthesis of bicyclic spirocompounds.

As part of our research on bicyclic spirocompounds (Fihi et al., 1995; Roussel et al., 2000, 2003; Daran et al., 2006), we reported that methylene lactones react with 1,3-dipoles with high selectivity. In a previous article (Fihi et al., 2004) we reported that 1,3-dipolar cycloaddition of arylnitriloxydes and N-Phenylarylnitrilimines to 5-chloro-2-methylene-1,3,3-trimethylindoline is regiospecific. Arylnitriloxydes reactions lead to spiroheterocyclic compounds, whereas N-phenylarylnitrilimines reactions afforded evolutives products.

We report here, the cycloaddition of C-phenyl-N-phenylnitrone (2) to 2-methylene-1,3,3-trimethylindoline (1). The reaction produced a mixture of diastereoisomers (Fig. 2). The ratio (77 / 23%) of which was evaluated by ¹HNMR (performed on the crude reaction mixture). To confirm unambiguously the structure assignment of (3) and (3'), and to establish the stereochemistry of each spiroheterocycle, an X-ray structural analyses was carried out on the major spirocompound, because the ¹H and ¹³CNMR studies did not provide unambiguous information.

The stereochemistry of the major diastereoisomer, S,R/R,S, is confirmed by the X-ray analyses (Fig. 1). The oxazole and the pyrole rings have an envelope conformation with puckering parameters Q(2)= 0.399 (3)°, ϕ(2)= 218.9 (5)° and Q(2)= 0.274 (3)°, ϕ(2)= 218.9 (7)° (Cremer & Pople, 1975). The packing is stabilized by weak C—H···π interactions involving the phenyl attached to the nitrogen of the oxazole and the phenyl of the indole fragment (Table 1: Cg1is the centroid of the C21—C26 ring and Cg2 is the centroid of the C3—C8 ring).

Related literature top

For general background, see: Alonso-Perarnau et al. (1997); Cacciarini et al. (2000); Pariera et al. (1993). For related studies, see: Daran et al. (2006); Fihi et al. (1995, 2004); Roussel et al. (2000, 2003). For the synthetic procedure, see: Brüning et al. (1973). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

2-Methylene-1,3,3-trimethylindoline (1) is a commercial product. C-phenyl, N-diphenylnitrone (2) was synthesized according to the literature procedure (Brüning et al., 1973). A solution of (2) (1 g, 6 mmol), (1) (1,12 g, 6 mmol) in ethylacetate (40 ml) was stirred at reflux for 24 h. The solvent was then evaporated under reduced pressure. The residue was crystallized from ethanol, leading to a mixture of diastereiosomers (3) and (3'). They were separated and purified by chromatography on silica gel (eluant: dichloromethane / hexane: 10 / 90). The spirocompounds were finally recrystallized from dichloromethane.

Computing details top

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, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular view of (I). Displacement ellipsoids are drawn at the 30% probability level and H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. The formation of the title compound.

1',3',3'-Trimethyl-2,3-diphenyl-2,3-dihydroisoxazole-5(4H)-spiro- 2'-indoline top

Crystal data top

C₂₅H₂₆N₂O	F(000) = 792
M_r = 370.48	D_x = 1.225 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 8000 reflections
a = 18.0393 (18) Å	θ = 1.7–26.2°
b = 8.9854 (7) Å	µ = 0.08 mm⁻¹
c = 12.3947 (9) Å	T = 180 K
V = 2009.1 (3) Å³	Prism, colorless
Z = 4	0.48 × 0.36 × 0.28 mm

Data collection top

Stoe IPDS diffractometer	1581 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.059
Graphite monochromator	θ_max = 26.0°, θ_min = 2.5°
ϕ scans	h = −22→22
19030 measured reflections	k = −11→11
2021 independent reflections	l = −14→14

Refinement top

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H-atom parameters constrained
S = 1.15	w = 1/[σ²(F_o²) + (0.061P)²] where P = (F_o² + 2F_c²)/3
2021 reflections	(Δ/σ)_max = 0.007
256 parameters	Δρ_max = 0.26 e Å⁻³
1 restraint	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₂₅H₂₆N₂O	V = 2009.1 (3) Å³
M_r = 370.48	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 18.0393 (18) Å	µ = 0.08 mm⁻¹
b = 8.9854 (7) Å	T = 180 K
c = 12.3947 (9) Å	0.48 × 0.36 × 0.28 mm

Data collection top

Stoe IPDS diffractometer	1581 reflections with I > 2σ(I)
19030 measured reflections	R_int = 0.059
2021 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	1 restraint
wR(F²) = 0.105	H-atom parameters constrained
S = 1.15	Δρ_max = 0.26 e Å⁻³
2021 reflections	Δρ_min = −0.15 e Å⁻³
256 parameters

Special details top

Experimental. The data were collected on a Stoe Imaging Plate Diffraction System (IPDS). The crystal-to-detector distance was 70 mm. 167 frames (4 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 97.4% complete to at least 26.04°. Crystal decay was monitored by measuring 200 reflections per frame.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.43438 (17)	0.9280 (3)	0.0510 (3)	0.0360 (7)
C2	0.52004 (18)	0.9356 (3)	0.0701 (3)	0.0398 (7)
C3	0.53941 (16)	1.0776 (3)	0.0091 (3)	0.0346 (7)
C4	0.60643 (18)	1.1346 (4)	−0.0231 (3)	0.0470 (8)
H4	0.6508	1.0802	−0.0111	0.056*
C5	0.6086 (2)	1.2734 (4)	−0.0738 (3)	0.0523 (9)
H5	0.6547	1.3141	−0.0964	0.063*
C6	0.5439 (2)	1.3510 (4)	−0.0909 (3)	0.0482 (9)
H6	0.5460	1.4452	−0.1256	0.058*
C7	0.47568 (18)	1.2952 (3)	−0.0588 (3)	0.0412 (7)
H7	0.4312	1.3493	−0.0710	0.049*
C8	0.47495 (15)	1.1576 (3)	−0.0082 (3)	0.0327 (7)
C9	0.34450 (16)	0.7260 (3)	0.0744 (3)	0.0363 (7)
H9	0.2955	0.7656	0.0500	0.044*
C10	0.38766 (19)	0.8462 (4)	0.1354 (3)	0.0458 (8)
H10A	0.3531	0.9161	0.1713	0.055*
H10B	0.4199	0.8006	0.1908	0.055*
C21	0.36716 (14)	0.6294 (3)	−0.1120 (2)	0.0294 (6)
C22	0.40480 (18)	0.6491 (3)	−0.2083 (3)	0.0367 (7)
H22	0.4453	0.7164	−0.2117	0.044*
C23	0.38362 (18)	0.5708 (3)	−0.2998 (3)	0.0429 (7)
H23	0.4091	0.5856	−0.3660	0.051*
C24	0.32514 (17)	0.4710 (4)	−0.2943 (3)	0.0438 (8)
H24	0.3110	0.4163	−0.3565	0.053*
C25	0.28787 (18)	0.4513 (4)	−0.1993 (3)	0.0414 (8)
H25	0.2482	0.3821	−0.1959	0.050*
C26	0.30746 (15)	0.5317 (3)	−0.1074 (3)	0.0352 (7)
H26	0.2803	0.5199	−0.0423	0.042*
C91	0.33383 (16)	0.5862 (3)	0.1405 (3)	0.0359 (7)
C92	0.39087 (17)	0.4871 (3)	0.1574 (3)	0.0418 (8)
H92	0.4380	0.5056	0.1259	0.050*
C93	0.3806 (2)	0.3610 (4)	0.2195 (3)	0.0511 (9)
H93	0.4205	0.2936	0.2302	0.061*
C94	0.3131 (2)	0.3330 (4)	0.2658 (3)	0.0537 (9)
H94	0.3064	0.2460	0.3082	0.064*
C95	0.2549 (2)	0.4299 (4)	0.2513 (3)	0.0532 (9)
H95	0.2083	0.4109	0.2841	0.064*
C96	0.26512 (18)	0.5563 (4)	0.1878 (3)	0.0462 (8)
H96	0.2249	0.6229	0.1767	0.055*
C111	0.33893 (17)	1.1202 (4)	0.0002 (4)	0.0526 (9)
H11A	0.3290	1.2248	0.0175	0.079*
H11B	0.3032	1.0567	0.0380	0.079*
H11C	0.3342	1.1051	−0.0778	0.079*
C211	0.5371 (2)	0.9600 (4)	0.1901 (3)	0.0531 (9)
H21A	0.5894	0.9871	0.1986	0.080*
H21B	0.5270	0.8682	0.2301	0.080*
H21C	0.5058	1.0403	0.2181	0.080*
C212	0.5604 (2)	0.7992 (4)	0.0285 (4)	0.0576 (11)
H21D	0.5484	0.7845	−0.0479	0.086*
H21E	0.5448	0.7117	0.0698	0.086*
H21F	0.6139	0.8134	0.0366	0.086*
N1	0.41386 (13)	1.0819 (2)	0.0341 (2)	0.0369 (6)
N2	0.39329 (13)	0.7023 (2)	−0.0180 (2)	0.0323 (6)
O1	0.41789 (11)	0.8501 (2)	−0.04964 (17)	0.0370 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0486 (17)	0.0268 (14)	0.0327 (18)	−0.0061 (13)	0.0006 (14)	−0.0026 (13)
C2	0.0508 (18)	0.0289 (15)	0.040 (2)	0.0018 (13)	−0.0082 (15)	0.0004 (13)
C3	0.0405 (16)	0.0306 (15)	0.0327 (19)	−0.0027 (12)	0.0001 (13)	0.0003 (12)
C4	0.0412 (17)	0.0488 (19)	0.051 (2)	−0.0023 (14)	0.0057 (15)	−0.0044 (17)
C5	0.061 (2)	0.052 (2)	0.045 (2)	−0.0220 (17)	0.0183 (17)	−0.0051 (16)
C6	0.075 (2)	0.0369 (18)	0.033 (2)	−0.0124 (16)	0.0080 (16)	−0.0010 (14)
C7	0.0545 (18)	0.0294 (16)	0.040 (2)	−0.0016 (13)	−0.0020 (15)	0.0007 (14)
C8	0.0393 (15)	0.0278 (15)	0.0308 (17)	−0.0033 (11)	0.0016 (13)	−0.0016 (12)
C9	0.0392 (16)	0.0353 (15)	0.0344 (19)	−0.0024 (13)	0.0062 (13)	−0.0029 (12)
C10	0.0589 (19)	0.0389 (17)	0.040 (2)	−0.0125 (14)	0.0075 (16)	−0.0062 (15)
C21	0.0326 (14)	0.0234 (13)	0.0322 (18)	0.0021 (11)	−0.0030 (12)	−0.0014 (12)
C22	0.0439 (16)	0.0333 (15)	0.0328 (19)	−0.0024 (12)	0.0017 (13)	0.0000 (13)
C23	0.0537 (18)	0.0432 (17)	0.0318 (18)	0.0047 (14)	0.0002 (15)	−0.0054 (15)
C24	0.0491 (18)	0.0433 (17)	0.039 (2)	0.0008 (13)	−0.0094 (16)	−0.0094 (15)
C25	0.0419 (16)	0.0399 (16)	0.042 (2)	−0.0044 (13)	−0.0055 (15)	−0.0063 (15)
C26	0.0323 (14)	0.0364 (15)	0.0369 (18)	−0.0013 (12)	−0.0045 (13)	0.0005 (14)
C91	0.0445 (16)	0.0323 (15)	0.0307 (17)	−0.0099 (13)	0.0010 (14)	−0.0021 (13)
C92	0.0427 (16)	0.0409 (17)	0.042 (2)	−0.0040 (13)	−0.0009 (14)	−0.0015 (15)
C93	0.061 (2)	0.0437 (19)	0.048 (2)	−0.0014 (15)	−0.0055 (17)	0.0017 (16)
C94	0.066 (2)	0.0429 (19)	0.052 (2)	−0.0193 (17)	−0.0025 (18)	0.0060 (17)
C95	0.054 (2)	0.058 (2)	0.047 (2)	−0.0182 (18)	0.0122 (17)	0.0016 (18)
C96	0.0472 (17)	0.0453 (18)	0.046 (2)	−0.0044 (14)	0.0023 (16)	−0.0026 (16)
C111	0.0396 (17)	0.0475 (18)	0.071 (3)	0.0017 (14)	−0.0049 (18)	−0.0098 (18)
C211	0.066 (2)	0.0489 (19)	0.045 (2)	−0.0085 (16)	−0.0146 (18)	0.0061 (17)
C212	0.055 (2)	0.0375 (18)	0.081 (3)	0.0098 (16)	−0.0048 (19)	−0.0012 (18)
N1	0.0374 (13)	0.0269 (12)	0.0464 (17)	−0.0029 (11)	0.0025 (11)	−0.0012 (12)
N2	0.0410 (13)	0.0248 (12)	0.0311 (15)	−0.0095 (10)	0.0016 (10)	−0.0016 (11)
O1	0.0570 (13)	0.0239 (10)	0.0302 (12)	−0.0113 (8)	0.0029 (10)	−0.0018 (9)

Geometric parameters (Å, º) top

C1—N1	1.446 (4)	C23—C24	1.386 (5)
C1—O1	1.461 (4)	C23—H23	0.9500
C1—C10	1.531 (5)	C24—C25	1.367 (5)
C1—C2	1.565 (4)	C24—H24	0.9500
C2—C212	1.516 (5)	C25—C26	1.395 (4)
C2—C3	1.523 (4)	C25—H25	0.9500
C2—C211	1.534 (5)	C26—H26	0.9500
C3—C4	1.372 (4)	C91—C92	1.377 (4)
C3—C8	1.384 (4)	C91—C96	1.397 (4)
C4—C5	1.397 (5)	C92—C93	1.382 (5)
C4—H4	0.9500	C92—H92	0.9500
C5—C6	1.376 (5)	C93—C94	1.369 (6)
C5—H5	0.9500	C93—H93	0.9500
C6—C7	1.388 (5)	C94—C95	1.375 (6)
C6—H6	0.9500	C94—H94	0.9500
C7—C8	1.387 (4)	C95—C96	1.393 (5)
C7—H7	0.9500	C95—H95	0.9500
C8—N1	1.397 (4)	C96—H96	0.9500
C9—N2	1.460 (4)	C111—N1	1.457 (4)
C9—C91	1.512 (4)	C111—H11A	0.9800
C9—C10	1.531 (4)	C111—H11B	0.9800
C9—H9	1.0000	C111—H11C	0.9800
C10—H10A	0.9900	C211—H21A	0.9800
C10—H10B	0.9900	C211—H21B	0.9800
C21—C22	1.384 (4)	C211—H21C	0.9800
C21—C26	1.390 (4)	C212—H21D	0.9800
C21—N2	1.417 (4)	C212—H21E	0.9800
C22—C23	1.388 (5)	C212—H21F	0.9800
C22—H22	0.9500	N2—O1	1.454 (3)

N1—C1—O1	106.4 (2)	C25—C24—H24	120.0
N1—C1—C10	114.6 (3)	C23—C24—H24	120.0
O1—C1—C10	104.0 (2)	C24—C25—C26	120.8 (3)
N1—C1—C2	103.5 (2)	C24—C25—H25	119.6
O1—C1—C2	110.6 (2)	C26—C25—H25	119.6
C10—C1—C2	117.4 (3)	C21—C26—C25	119.3 (3)
C212—C2—C3	113.4 (3)	C21—C26—H26	120.3
C212—C2—C211	110.5 (3)	C25—C26—H26	120.3
C3—C2—C211	108.4 (3)	C92—C91—C96	118.4 (3)
C212—C2—C1	112.8 (3)	C92—C91—C9	121.6 (3)
C3—C2—C1	100.8 (2)	C96—C91—C9	120.0 (3)
C211—C2—C1	110.6 (3)	C91—C92—C93	120.9 (3)
C4—C3—C8	120.1 (3)	C91—C92—H92	119.5
C4—C3—C2	131.2 (3)	C93—C92—H92	119.5
C8—C3—C2	108.6 (3)	C94—C93—C92	120.2 (3)
C3—C4—C5	119.3 (3)	C94—C93—H93	119.9
C3—C4—H4	120.4	C92—C93—H93	119.9
C5—C4—H4	120.4	C93—C94—C95	120.5 (3)
C6—C5—C4	119.9 (3)	C93—C94—H94	119.8
C6—C5—H5	120.1	C95—C94—H94	119.8
C4—C5—H5	120.1	C94—C95—C96	119.3 (3)
C5—C6—C7	121.7 (3)	C94—C95—H95	120.3
C5—C6—H6	119.2	C96—C95—H95	120.3
C7—C6—H6	119.2	C95—C96—C91	120.7 (3)
C8—C7—C6	117.4 (3)	C95—C96—H96	119.7
C8—C7—H7	121.3	C91—C96—H96	119.7
C6—C7—H7	121.3	N1—C111—H11A	109.5
C3—C8—C7	121.7 (3)	N1—C111—H11B	109.5
C3—C8—N1	110.6 (3)	H11A—C111—H11B	109.5
C7—C8—N1	127.7 (3)	N1—C111—H11C	109.5
N2—C9—C91	112.4 (2)	H11A—C111—H11C	109.5
N2—C9—C10	100.6 (2)	H11B—C111—H11C	109.5
C91—C9—C10	112.6 (3)	C2—C211—H21A	109.5
N2—C9—H9	110.3	C2—C211—H21B	109.5
C91—C9—H9	110.3	H21A—C211—H21B	109.5
C10—C9—H9	110.3	C2—C211—H21C	109.5
C1—C10—C9	106.4 (3)	H21A—C211—H21C	109.5
C1—C10—H10A	110.5	H21B—C211—H21C	109.5
C9—C10—H10A	110.5	C2—C212—H21D	109.5
C1—C10—H10B	110.5	C2—C212—H21E	109.5
C9—C10—H10B	110.5	H21D—C212—H21E	109.5
H10A—C10—H10B	108.6	C2—C212—H21F	109.5
C22—C21—C26	119.7 (3)	H21D—C212—H21F	109.5
C22—C21—N2	119.1 (2)	H21E—C212—H21F	109.5
C26—C21—N2	121.0 (3)	C8—N1—C1	108.5 (2)
C21—C22—C23	120.3 (3)	C8—N1—C111	120.6 (3)
C21—C22—H22	119.8	C1—N1—C111	120.4 (2)
C23—C22—H22	119.8	C21—N2—O1	107.6 (2)
C24—C23—C22	119.8 (3)	C21—N2—C9	120.8 (2)
C24—C23—H23	120.1	O1—N2—C9	105.2 (2)
C22—C23—H23	120.1	N2—O1—C1	105.6 (2)
C25—C24—C23	120.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···Cg1ⁱ	0.95	2.89	3.735 (3)	149
C23—H23···Cg2ⁱⁱ	0.95	2.95	3.803 (4)	150

Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y+2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₅H₂₆N₂O
M_r	370.48
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	180
a, b, c (Å)	18.0393 (18), 8.9854 (7), 12.3947 (9)
V (Å³)	2009.1 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.48 × 0.36 × 0.28

Data collection
Diffractometer	Stoe IPDS diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	19030, 2021, 1581
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.105, 1.15
No. of reflections	2021
No. of parameters	256
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.15

Computer programs: IPDS (Stoe, 2000), X-RED (Stoe, 1996), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997).