2-(4-Methoxy­phenyl)-5-(4-methyl­pent-3-enyl)-2,3,3a,4,7,7a-hexa­hydro-1H-iso­indole-1,3-dione

Lynch, D.E.; McClenaghan, I.

doi:10.1107/S160053680300120X

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2-(4-Methoxyphenyl)-5-(4-methylpent-3-enyl)-2,3,3a,4,7,7a-hexahydro-1H-isoindole-1,3-dione

D. E. Lynch and I. McClenaghan

The structure of the title compound, C₂₁H₂₅NO₃, comprises a U-shaped molecule with two disordered atoms in the pentene chain. The two components of the two disordered alkane C atoms exist with unequal partial occupancies of 0.70 and 0.30. The dihedral angle between the planar imide ring [r.m.s. deviation 0.038 (3) Å] and the phenyl ring is 62.56 (14)°. C—H

O close contacts are observed from two different aromatic C atoms to the two oxo O atoms.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680300120X/na6195sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680300120X/na6195Isup2.hkl Contains datablock I

CCDC reference: 204704

checkCIF report

Key indicators

Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.008 Å
R factor = 0.074
wR factor = 0.223
Data-to-parameter ratio = 11.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           25.00
         From the CIF: _reflns_number_total               2934
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns         3148
         Completeness (_total/calc)             93.20%
          Alert C: < 95% complete

RINTA_01  Alert C The value of Rint is greater than 0.10
          Rint given   0.129


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 2 Alert Level C = Please check

Comment top

The title compound, (I), was prepared by a Diels–Alder reaction between 1-(4-methoxyphenyl)-3-pyrroline-2,5-dione and 7-methyl-3-methyleneocta-1,6-diene. The naming of (I) has proved difficult with several variants for the main ring system being previously given. The basic unsubstituted structure (Kirfel, 1976) was named as a tetrahydrophthalimide and several other substituted analogues have been similarly named, although numbering schemes differ significantly as to which four atoms are saturated. Other names include hydroisoindoline-1,3-dione (with differing numbers of saturated C atoms), cyclohex-4-ene-1,2-dicarboximide and azabicyclo[4.3.0]non-3-ene-7,9-dione, with the first being the most popular. The structure of (I) comprises a U-shaped molecule with two disordered atoms in the pentene chain (Fig. 1). The shape is dependent on the boat conformation displayed by the hydrophthalimide group. Of 136 current structures (Cambridge Structural Database, September 2002 release; Allen, 2002) containing a phthalimide ring similar to (I), only 48 do not have any bridging across the cyclohexene ring. From the 48, 23 compounds contain an N-phenyl moiety, of which 11 compounds share a similar boat conformation to (I). This conformation is also displayed by 5-(2-methyl-1,3-dioxo-2,3,3a,4,7,7a-hexahydro-1H-isoindol-5-yl)pent-2-enoic acid (Yliniemala et al., 1995) which is the nearest structural analogue to (I). In this structure, the pent-2-enoic acid chain is not disordered. In (I), the two components (A and B) of the two disordered alkane C atoms (C51 and C52) exist with unequal partial occupancies of 0.70 and 0.30, respectively, for A and B. The dihedral angle between the planar imide ring [r.m.s. deviation 0.038 (3) Å] and the phenyl ring is 62.56 (14)°. C—H···O close contacts are observed from two different aromatic C atoms to the two oxo O atoms (Table 1).

Experimental top

The title compound was obtained from Key Organics Ltd and crystals were grown from ethanol solution.

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON97 (Spek, 1997); software used to prepare material for publication: SHELXL97.

Figures top

Fig. 1. The molecular configuration and atom-numbering scheme for the title compound, showing ellipsoids at the 50% probability level.

2-(4-Methoxyphenyl)-5-(4-methylpent-3-enyl)-2,3,3a,4,7,7a-hexahydro- 1H-isoindole-1,3-dione top

Crystal data top

C₂₁H₂₅NO₃	F(000) = 728
M_r = 339.42	D_x = 1.262 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 17.001 (2) Å	Cell parameters from 20434 reflections
b = 6.5492 (10) Å	θ = 2.9–27.5°
c = 17.145 (3) Å	µ = 0.08 mm⁻¹
β = 110.584 (5)°	T = 150 K
V = 1787.1 (5) Å³	Prism, colourless
Z = 4	0.20 × 0.15 × 0.03 mm

Data collection top

Bruker–Nonius KappaCCD area-detector diffractometer	2934 independent reflections
Radiation source: Bruker–Nonius FR591 rotating anode	1368 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.129
Detector resolution: 9.091 pixels mm^-1	θ_max = 25.0°, θ_min = 3.2°
ϕ and ω scans	h = −18→20
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −7→7
T_min = 0.983, T_max = 0.998	l = −19→20
8778 measured reflections

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)] = 0.074	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.223	H-atom parameters constrained
S = 0.94	w = 1/[σ²(F_o²) + (0.1159P)²] where P = (F_o² + 2F_c²)/3
2934 reflections	(Δ/σ)_max < 0.001
247 parameters	Δρ_max = 0.30 e Å⁻³
29 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₂₁H₂₅NO₃	V = 1787.1 (5) Å³
M_r = 339.42	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.001 (2) Å	µ = 0.08 mm⁻¹
b = 6.5492 (10) Å	T = 150 K
c = 17.145 (3) Å	0.20 × 0.15 × 0.03 mm
β = 110.584 (5)°

Data collection top

Bruker–Nonius KappaCCD area-detector diffractometer	2934 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	1368 reflections with I > 2σ(I)
T_min = 0.983, T_max = 0.998	R_int = 0.129
8778 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.074	29 restraints
wR(F²) = 0.223	H-atom parameters constrained
S = 0.94	Δρ_max = 0.30 e Å⁻³
2934 reflections	Δρ_min = −0.32 e Å⁻³
247 parameters

Special details top

Geometry. Mean plane data ex SHELXL97 for molecule (I) ############################################

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

6.8624 (0.0327) x + 2.8607 (0.0127) y + 10.4700 (0.0286) z = 4.1434 (0.0199)

* −0.0159 (0.0025) C1 * 0.0455 (0.0024) N2 * −0.0532 (0.0027) C3 * 0.0403 (0.0028) C9 * −0.0166 (0.0027) C8

Rms deviation of fitted atoms = 0.0376

1.3752 (0.0278) x + 3.1373 (0.0091) y − 14.5166 (0.0145) z = 1.2319 (0.0115)

Angle to previous plane (with approximate e.s.d.) = 62.56 (0.14)

* −0.0017 (0.0028) C21 * 0.0040 (0.0028) C22 * −0.0023 (0.0028) C23 * −0.0016 (0.0028) C24 * 0.0039 (0.0027) C25 * −0.0022 (0.0027) C26

Rms deviation of fitted atoms = 0.0028

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	−0.2069 (3)	1.1541 (7)	0.2145 (3)	0.0426 (11)
O1	−0.19386 (19)	0.9842 (5)	0.24579 (19)	0.0563 (9)
N2	−0.16329 (19)	1.2394 (5)	0.16848 (19)	0.0354 (9)
C21	−0.0957 (3)	1.1381 (6)	0.1522 (2)	0.0370 (10)
C22	−0.1080 (3)	0.9563 (6)	0.1113 (2)	0.0399 (11)
H22	−0.1623	0.8960	0.0926	0.050*
C23	−0.0421 (3)	0.8575 (6)	0.0966 (3)	0.0393 (11)
H23	−0.0505	0.7299	0.0686	0.049*
C24	0.0358 (3)	0.9498 (6)	0.1239 (2)	0.0394 (11)
C25	0.0473 (3)	1.1336 (6)	0.1644 (3)	0.0411 (11)
H25	0.1013	1.1956	0.1823	0.051*
C26	−0.0178 (3)	1.2307 (6)	0.1796 (2)	0.0399 (11)
H26	−0.0092	1.3577	0.2082	0.050*
O21	0.10419 (17)	0.8646 (4)	0.11353 (18)	0.0479 (8)
C27	0.0941 (3)	0.6843 (7)	0.0644 (3)	0.0510 (12)
H271	0.0763	0.5714	0.0919	0.064*
H272	0.1476	0.6496	0.0581	0.064*
H273	0.0513	0.7079	0.0093	0.064*
C3	−0.1976 (3)	1.4218 (7)	0.1317 (3)	0.0434 (11)
O3	−0.17827 (18)	1.5097 (4)	0.07968 (19)	0.0518 (9)
C4	−0.3450 (3)	1.5392 (9)	0.0946 (4)	0.0791 (18)
H41	−0.3855	1.6036	0.1169	0.099*
H42	−0.3320	1.6386	0.0574	0.099*
C5	−0.3833 (3)	1.3527 (12)	0.0465 (3)	0.0704 (17)
C51A	−0.4068 (5)	1.3958 (12)	−0.0477 (4)	0.073 (2)	0.70
H511	−0.3603	1.4696	−0.0574	0.091*	0.70
H512	−0.4575	1.4835	−0.0673	0.091*	0.70
C51B	−0.4308 (10)	1.274 (3)	−0.0427 (9)	0.076 (6)	0.30
H513	−0.4835	1.3523	−0.0675	0.095*	0.30
H514	−0.4457	1.1287	−0.0403	0.095*	0.30
C52A	−0.4242 (5)	1.1936 (12)	−0.0973 (5)	0.075 (2)	0.70
H523	−0.4535	1.2222	−0.1573	0.094*	0.70
H524	−0.4608	1.1049	−0.0780	0.094*	0.70
C52B	−0.3773 (14)	1.295 (3)	−0.0984 (12)	0.094 (7)	0.30
H521	−0.3344	1.4042	−0.0787	0.118*	0.30
H522	−0.4121	1.3194	−0.1575	0.118*	0.30
C53	−0.3383 (4)	1.0818 (11)	−0.0842 (4)	0.097 (2)
H53	−0.2874	1.1382	−0.0471	0.121*
C54	−0.3365 (3)	0.9123 (9)	−0.1238 (3)	0.0637 (15)
C55	−0.2582 (3)	0.7912 (8)	−0.1072 (3)	0.0641 (14)
H551	−0.2099	0.8717	−0.0729	0.080*
H552	−0.2516	0.7568	−0.1602	0.080*
H553	−0.2618	0.6654	−0.0777	0.080*
C56	−0.4106 (3)	0.8276 (9)	−0.1907 (4)	0.0928 (19)
H561	−0.4273	0.6989	−0.1719	0.116*
H562	−0.3962	0.8025	−0.2405	0.116*
H563	−0.4571	0.9252	−0.2041	0.116*
C6	−0.3888 (3)	1.1894 (11)	0.0879 (4)	0.0758 (17)
H6	−0.4113	1.0666	0.0593	0.095*
C7	−0.3595 (3)	1.1980 (8)	0.1807 (3)	0.0653 (15)
H71	−0.3561	1.0575	0.2030	0.082*
H72	−0.4009	1.2746	0.1978	0.082*
C8	−0.2733 (3)	1.3006 (7)	0.2179 (3)	0.0479 (12)
H8	−0.2628	1.3423	0.2768	0.060*
C9	−0.2638 (3)	1.4835 (7)	0.1672 (3)	0.0492 (12)
H9	−0.2438	1.6044	0.2046	0.061*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.042 (3)	0.042 (3)	0.041 (3)	0.003 (2)	0.011 (2)	−0.001 (2)
O1	0.058 (2)	0.053 (2)	0.067 (2)	0.0071 (17)	0.0332 (18)	0.0113 (18)
N2	0.034 (2)	0.034 (2)	0.041 (2)	0.0016 (16)	0.0164 (17)	0.0014 (17)
C21	0.034 (3)	0.038 (3)	0.037 (2)	−0.002 (2)	0.009 (2)	−0.001 (2)
C22	0.030 (3)	0.048 (3)	0.040 (3)	−0.005 (2)	0.010 (2)	−0.005 (2)
C23	0.036 (3)	0.034 (2)	0.048 (3)	−0.002 (2)	0.015 (2)	−0.006 (2)
C24	0.038 (3)	0.044 (3)	0.039 (3)	0.001 (2)	0.016 (2)	−0.002 (2)
C25	0.032 (3)	0.044 (3)	0.048 (3)	0.000 (2)	0.015 (2)	−0.001 (2)
C26	0.039 (3)	0.039 (2)	0.040 (3)	−0.007 (2)	0.012 (2)	−0.003 (2)
O21	0.0316 (18)	0.0525 (19)	0.061 (2)	0.0032 (14)	0.0187 (15)	−0.0059 (16)
C27	0.042 (3)	0.052 (3)	0.058 (3)	0.009 (2)	0.018 (2)	−0.007 (3)
C3	0.042 (3)	0.041 (3)	0.049 (3)	−0.002 (2)	0.016 (2)	0.004 (2)
O3	0.047 (2)	0.0461 (18)	0.065 (2)	0.0022 (15)	0.0223 (18)	0.0094 (17)
C4	0.051 (4)	0.099 (5)	0.098 (5)	0.034 (3)	0.039 (3)	0.046 (4)
C5	0.038 (3)	0.119 (5)	0.049 (4)	0.020 (3)	0.009 (3)	−0.006 (4)
C51A	0.059 (4)	0.091 (4)	0.075 (4)	0.005 (3)	0.030 (3)	0.013 (4)
C51B	0.072 (7)	0.073 (7)	0.080 (7)	0.006 (5)	0.023 (5)	−0.006 (5)
C52A	0.064 (4)	0.089 (4)	0.064 (4)	0.006 (4)	0.013 (3)	−0.005 (4)
C52B	0.099 (8)	0.093 (8)	0.091 (8)	0.000 (5)	0.033 (5)	0.001 (5)
C53	0.115 (6)	0.118 (5)	0.051 (4)	0.033 (4)	0.021 (3)	0.000 (4)
C54	0.058 (4)	0.079 (4)	0.056 (3)	0.002 (3)	0.021 (3)	0.010 (3)
C55	0.047 (3)	0.084 (4)	0.061 (3)	−0.002 (3)	0.018 (3)	0.002 (3)
C56	0.058 (4)	0.102 (5)	0.102 (5)	0.003 (3)	0.008 (4)	0.010 (4)
C6	0.031 (3)	0.101 (5)	0.094 (5)	−0.002 (3)	0.021 (3)	−0.021 (4)
C7	0.046 (3)	0.072 (3)	0.087 (4)	−0.001 (3)	0.035 (3)	−0.003 (3)
C8	0.042 (3)	0.058 (3)	0.046 (3)	0.005 (2)	0.018 (2)	−0.006 (2)
C9	0.044 (3)	0.045 (3)	0.059 (3)	0.008 (2)	0.019 (3)	−0.002 (2)

Geometric parameters (Å, º) top

C1—O1	1.222 (5)	C51A—H512	0.99
C1—N2	1.377 (5)	C52A—C53	1.577 (9)
C1—C8	1.498 (6)	C52A—H523	0.99
N2—C3	1.381 (5)	C52A—H524	0.99
N2—C21	1.438 (5)	C53—H53	0.95
C21—C22	1.359 (5)	C51B—C52B	1.539 (16)
C21—C26	1.380 (5)	C51B—H513	0.99
C22—C23	1.391 (5)	C51B—H514	0.99
C22—H22	0.95	C52B—H521	0.99
C23—C24	1.379 (6)	C52B—H522	0.99
C23—H23	0.95	C54—C53	1.307 (7)
C24—O21	1.357 (5)	C54—C56	1.481 (7)
C24—C25	1.369 (5)	C54—C55	1.488 (6)
C25—C26	1.378 (5)	C55—H551	0.98
C25—H25	0.95	C55—H552	0.98
C26—H26	0.95	C55—H553	0.98
O21—C27	1.426 (5)	C56—H561	0.98
C27—H271	0.98	C56—H562	0.98
C27—H272	0.98	C56—H563	0.98
C27—H273	0.98	C6—C5	1.305 (7)
C3—O3	1.200 (5)	C6—C7	1.491 (7)
C3—C9	1.511 (6)	C6—H6	0.95
C4—C5	1.489 (8)	C7—C8	1.532 (6)
C4—C9	1.542 (7)	C7—H71	0.99
C4—H41	0.99	C7—H72	0.99
C4—H42	0.99	C8—C9	1.522 (6)
C5—C51A	1.548 (8)	C8—H8	1.00
C51A—C52A	1.545 (9)	C9—H9	1.00
C51A—H511	0.99

O1—C1—N2	124.7 (4)	C54—C56—H562	109.5
O1—C1—C8	126.1 (4)	H561—C56—H562	109.5
N2—C1—C8	109.1 (4)	C54—C56—H563	109.5
C1—N2—C3	112.7 (3)	H561—C56—H563	109.5
C1—N2—C21	123.6 (3)	H562—C56—H563	109.5
C3—N2—C21	123.3 (3)	C5—C6—C7	119.2 (5)
C22—C21—C26	121.1 (4)	C5—C6—H6	120.4
C22—C21—N2	121.0 (4)	C7—C6—H6	120.4
C26—C21—N2	117.9 (4)	C6—C7—C8	111.9 (4)
C21—C22—C23	120.8 (4)	C6—C7—H71	109.2
C21—C22—H22	119.6	C8—C7—H71	109.2
C23—C22—H22	119.6	C6—C7—H72	109.2
C24—C23—C22	118.2 (4)	C8—C7—H72	109.2
C24—C23—H23	120.9	H71—C7—H72	107.9
C22—C23—H23	120.9	C1—C8—C9	104.4 (3)
O21—C24—C25	116.8 (4)	C1—C8—C7	109.0 (4)
O21—C24—C23	122.7 (4)	C9—C8—C7	112.6 (4)
C25—C24—C23	120.4 (4)	C1—C8—H8	110.2
C24—C25—C26	121.4 (4)	C9—C8—H8	110.2
C24—C25—H25	119.3	C7—C8—H8	110.2
C26—C25—H25	119.3	C3—C9—C8	105.3 (3)
C25—C26—C21	118.0 (4)	C3—C9—C4	108.7 (4)
C25—C26—H26	121.0	C8—C9—C4	113.7 (4)
C21—C26—H26	121.0	C3—C9—H9	109.7
C24—O21—C27	119.2 (3)	C8—C9—H9	109.7
O21—C27—H271	109.5	C4—C9—H9	109.7
O21—C27—H272	109.5	C6—C5—C4	118.1 (5)
H271—C27—H272	109.5	C6—C5—C51A	132.5 (7)
O21—C27—H273	109.5	C4—C5—C51A	109.3 (6)
H271—C27—H273	109.5	C5—C51A—C52A	110.4 (6)
H272—C27—H273	109.5	C5—C51A—H511	109.6
O3—C3—N2	124.9 (4)	C52A—C51A—H511	109.6
O3—C3—C9	127.5 (4)	C5—C51A—H512	109.6
N2—C3—C9	107.6 (4)	C52A—C51A—H512	109.6
C5—C4—C9	110.2 (4)	H511—C51A—H512	108.1
C5—C4—H41	109.6	C51A—C52A—C53	109.3 (6)
C9—C4—H41	109.6	C51A—C52A—H523	109.8
C5—C4—H42	109.6	C53—C52A—H523	109.8
C9—C4—H42	109.6	C51A—C52A—H524	109.8
H41—C4—H42	108.1	C53—C52A—H524	109.8
C53—C54—C56	123.5 (6)	H523—C52A—H524	108.3
C53—C54—C55	122.4 (5)	C54—C53—C52A	120.6 (6)
C56—C54—C55	114.0 (5)	C54—C53—H53	119.7
C54—C55—H551	109.5	C52A—C53—H53	119.7
C54—C55—H552	109.5	C52B—C51B—H513	109.3
H551—C55—H552	109.5	C52B—C51B—H514	109.3
C54—C55—H553	109.5	H513—C51B—H514	108.0
H551—C55—H553	109.5	C51B—C52B—H521	112.2
H552—C55—H553	109.5	C51B—C52B—H522	112.2
C54—C56—H561	109.5	H521—C52B—H522	109.8

O1—C1—N2—C3	172.3 (4)	N2—C1—C8—C9	0.5 (4)
C8—C1—N2—C3	−6.4 (4)	O1—C1—C8—C7	−57.6 (6)
O1—C1—N2—C21	−0.6 (6)	N2—C1—C8—C7	121.1 (4)
C8—C1—N2—C21	−179.3 (4)	C6—C7—C8—C1	−76.0 (5)
C1—N2—C21—C22	59.6 (5)	C6—C7—C8—C9	39.5 (6)
C3—N2—C21—C22	−112.6 (4)	O3—C3—C9—C8	169.8 (4)
C1—N2—C21—C26	−120.1 (4)	N2—C3—C9—C8	−8.6 (5)
C3—N2—C21—C26	67.7 (5)	O3—C3—C9—C4	47.6 (6)
C26—C21—C22—C23	0.6 (6)	N2—C3—C9—C4	−130.8 (4)
N2—C21—C22—C23	−179.1 (3)	C1—C8—C9—C3	4.8 (5)
C21—C22—C23—C24	−0.6 (6)	C7—C8—C9—C3	−113.3 (4)
C22—C23—C24—O21	179.2 (4)	C1—C8—C9—C4	123.8 (4)
C22—C23—C24—C25	0.1 (6)	C7—C8—C9—C4	5.6 (5)
O21—C24—C25—C26	−178.6 (3)	C5—C4—C9—C3	69.5 (5)
C23—C24—C25—C26	0.5 (6)	C5—C4—C9—C8	−47.4 (6)
C24—C25—C26—C21	−0.6 (6)	C7—C6—C5—C4	2.0 (7)
C22—C21—C26—C25	0.0 (6)	C7—C6—C5—C51A	179.6 (6)
N2—C21—C26—C25	179.7 (3)	C9—C4—C5—C6	45.5 (6)
C25—C24—O21—C27	−173.5 (3)	C9—C4—C5—C51A	−132.7 (5)
C23—C24—O21—C27	7.4 (6)	C6—C5—C51A—C52A	−12.8 (10)
C1—N2—C3—O3	−169.0 (4)	C4—C5—C51A—C52A	164.9 (6)
C21—N2—C3—O3	4.0 (6)	C5—C51A—C52A—C53	−74.5 (8)
C1—N2—C3—C9	9.5 (5)	C56—C54—C53—C52A	8.3 (9)
C21—N2—C3—C9	−177.5 (4)	C55—C54—C53—C52A	−174.0 (6)
C5—C6—C7—C8	−46.6 (7)	C51A—C52A—C53—C54	−176.2 (6)
O1—C1—C8—C9	−178.2 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22···O3ⁱ	0.95	2.55	3.134 (5)	120
C25—H25···O1ⁱⁱ	0.95	2.49	3.340 (5)	149

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

Experimental details

Crystal data
Chemical formula	C₂₁H₂₅NO₃
M_r	339.42
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	17.001 (2), 6.5492 (10), 17.145 (3)
β (°)	110.584 (5)
V (Å³)	1787.1 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.20 × 0.15 × 0.03

Data collection
Diffractometer	Bruker–Nonius KappaCCD area-detector diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1995)
T_min, T_max	0.983, 0.998
No. of measured, independent and observed [I > 2σ(I)] reflections	8778, 2934, 1368
R_int	0.129
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.074, 0.223, 0.94
No. of reflections	2934
No. of parameters	247
No. of restraints	29
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.32

Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), DENZO and COLLECT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON97 (Spek, 1997), SHELXL97.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22···O3ⁱ	0.95	2.55	3.134 (5)	120
C25—H25···O1ⁱⁱ	0.95	2.49	3.340 (5)	149

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

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