Ethyl 4-[(3,5-di-tert-butyl-2-hy­droxy­benzyl­idene)­amino]­benzoate

Shakir, R.M.; Ariffin, A.; Ng, S.W.

doi:10.1107/S1600536810041383

organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page o2915

https://doi.org/10.1107/S1600536810041383

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Ethyl 4-[(3,5-di-tert-butyl-2-hydroxybenzylidene)amino]benzoate

Raied Mustafa Shakir,^a Azhar Ariffin ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 23 September 2010; accepted 14 October 2010; online 23 October 2010)

The title compound, a Schiff base, C₂₄H₃₁NO₃, has a substituted aromatic ring at both ends of the azomethine linkage and these make a dihedral angle of 24.9 (1)°. There is an intramolecular hydrogen bond between the hydroxy group (donor) and the N atom of themazomethine linkage.

Related literature

For the use of the methyl ester analog of the title compound as a second-harmonic generation material, see: Sliwa et al. (2008 ).

Experimental

Crystal data

C₂₄H₃₁NO₃
M_r = 381.50
Monoclinic, P 2₁ /c
a = 18.4789 (18) Å
b = 10.7194 (11) Å
c = 10.7768 (10) Å
β = 97.437 (2)°
V = 2116.7 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.30 × 0.05 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer
19941 measured reflections
4855 independent reflections
3123 reflections with I > 2σ(I)
R_int = 0.065

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.142
S = 1.01
4855 reflections
257 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.64 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.87 (1)	1.80 (2)	2.609 (2)	154 (3)

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810041383/fl2320sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810041383/fl2320Isup2.hkl

checkCIF report

Comment top

The Schiff base, methyl 4-(di-3,5-tert-butyl-2-hydroxybenzylideneamino)benzoate, is a material suitable for second-harmonic generation as it has electron-donating and electron-withdrawing components that are critical for the manifestation of a permanent dipole (Sliwa et al., 2008). Replacing the methyl group with an ethyl moiety leads to (I), an intensely orange-colored compound (Scheme I, Fig. 1) that crystallizes in a centric space group and is, therefore, not suitable as an SHG material. The azomethine bond has an E-configuration; the two aromatic rings are aligned at 24.9 (1) °. The compound is neutral as the hydroxy group bears a hydrogen atom which is a donor in an intra-molecular H bond to the azomethine nitrogen atom (Table 1). There are no important intermolecular contacts; on the other hand, the compound appears to pack in such a way as to accomodate the bulky t-butyl groups as far as possible (Fig. 2).

Related literature top

For the use of the methyl ester analog of the title compound as a second-harmonic generation material, see: Sliwa et al. (2008).

Experimental top

Ethyl 4-aminobenzoate (0.35 g) dissolved in ethanol (5 ml) was added to 3,5-di-tert-butyl-2-hydroxybenzaldehyde (0.5 g) dissolved in ethanol (20 ml). Several drops of acetic acid were added. The solution was heated for 3 h. The solvent was evaporated and the product recrystallized from ethanol to yield orange prisms in 80% yield that were suitable for data collection.

Structure description top

For the use of the methyl ester analog of the title compound as a second-harmonic generation material, see: Sliwa et al. (2008).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of the C₂₄H₃₁NO₃ at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 2. Van der Waals packing of two adjacent molecules.

Ethyl 4-[(di-3,5-tert-butyl-2-hydroxybenzylidene)amino]benzoate top

Crystal data top

C₂₄H₃₁NO₃	F(000) = 824
M_r = 381.50	D_x = 1.197 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 18.4789 (18) Å	Cell parameters from 2280 reflections
b = 10.7194 (11) Å	θ = 2.2–23.8°
c = 10.7768 (10) Å	µ = 0.08 mm⁻¹
β = 97.437 (2)°	T = 100 K
V = 2116.7 (4) Å³	Prism, orange
Z = 4	0.30 × 0.05 × 0.05 mm

Data collection top

Bruker SMART APEX diffractometer	3123 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.065
Graphite monochromator	θ_max = 27.5°, θ_min = 2.2°
ω scans	h = −24→23
19941 measured reflections	k = −13→13
4855 independent reflections	l = −13→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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.142	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0558P)² + 1.1473P] where P = (F_o² + 2F_c²)/3
4855 reflections	(Δ/σ)_max = 0.001
257 parameters	Δρ_max = 0.64 e Å⁻³
1 restraint	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₂₄H₃₁NO₃	V = 2116.7 (4) Å³
M_r = 381.50	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 18.4789 (18) Å	µ = 0.08 mm⁻¹
b = 10.7194 (11) Å	T = 100 K
c = 10.7768 (10) Å	0.30 × 0.05 × 0.05 mm
β = 97.437 (2)°

Data collection top

Bruker SMART APEX diffractometer	3123 reflections with I > 2σ(I)
19941 measured reflections	R_int = 0.065
4855 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	1 restraint
wR(F²) = 0.142	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.64 e Å⁻³
4855 reflections	Δρ_min = −0.26 e Å⁻³
257 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.78175 (8)	0.89233 (13)	0.62825 (14)	0.0252 (3)
H1	0.7466 (13)	0.885 (3)	0.567 (2)	0.086 (12)*
O2	0.42198 (8)	0.93692 (14)	0.03223 (14)	0.0291 (4)
O3	0.43875 (7)	0.73467 (13)	−0.01081 (13)	0.0237 (3)
N1	0.67954 (9)	0.79668 (16)	0.46645 (16)	0.0222 (4)
C1	0.78970 (11)	0.77878 (18)	0.68363 (19)	0.0203 (4)
C2	0.84179 (10)	0.76051 (18)	0.78972 (18)	0.0186 (4)
C3	0.85050 (10)	0.63866 (18)	0.83515 (18)	0.0180 (4)
H3	0.8862	0.6243	0.9054	0.022*
C4	0.80999 (10)	0.53616 (18)	0.78384 (18)	0.0183 (4)
C5	0.75592 (10)	0.56031 (19)	0.68469 (18)	0.0199 (4)
H5	0.7253	0.4941	0.6509	0.024*
C6	0.74560 (10)	0.67938 (19)	0.63368 (18)	0.0201 (4)
C7	0.94204 (12)	0.9088 (2)	0.7566 (2)	0.0290 (5)
H7A	0.9137	0.9359	0.6780	0.044*
H7B	0.9735	0.8388	0.7402	0.044*
H7C	0.9722	0.9782	0.7930	0.044*
C8	0.88965 (11)	0.86740 (19)	0.84883 (19)	0.0219 (4)
C9	0.84263 (13)	0.9784 (2)	0.8811 (2)	0.0295 (5)
H9A	0.8124	1.0072	0.8051	0.044*
H9B	0.8744	1.0464	0.9158	0.044*
H9C	0.8112	0.9521	0.9428	0.044*
C10	0.93590 (13)	0.8274 (2)	0.9709 (2)	0.0304 (5)
H10A	0.9670	0.7569	0.9542	0.046*
H10B	0.9037	0.8024	1.0320	0.046*
H10C	0.9665	0.8974	1.0044	0.046*
C11	0.82432 (11)	0.40232 (18)	0.82969 (18)	0.0197 (4)
C12	0.75683 (11)	0.3511 (2)	0.8825 (2)	0.0254 (5)
H12A	0.7465	0.4030	0.9529	0.038*
H12B	0.7662	0.2652	0.9111	0.038*
H12C	0.7148	0.3526	0.8169	0.038*
C13	0.84080 (12)	0.3212 (2)	0.7192 (2)	0.0259 (5)
H13A	0.8838	0.3540	0.6858	0.039*
H13B	0.7988	0.3225	0.6535	0.039*
H13C	0.8502	0.2352	0.7479	0.039*
C14	0.88904 (11)	0.3930 (2)	0.9334 (2)	0.0247 (5)
H14A	0.9330	0.4251	0.9025	0.037*
H14B	0.8966	0.3056	0.9583	0.037*
H14C	0.8789	0.4423	1.0057	0.037*
C15	0.68922 (11)	0.69415 (19)	0.52586 (19)	0.0219 (4)
H15	0.6589	0.6250	0.4995	0.026*
C16	0.62487 (10)	0.8028 (2)	0.36008 (19)	0.0213 (4)
C17	0.59190 (11)	0.9167 (2)	0.3314 (2)	0.0235 (5)
H17	0.6062	0.9876	0.3815	0.028*
C18	0.53831 (11)	0.9279 (2)	0.23032 (19)	0.0228 (5)
H18	0.5157	1.0064	0.2116	0.027*
C19	0.51707 (10)	0.82475 (19)	0.15535 (19)	0.0202 (4)
C20	0.55214 (11)	0.7112 (2)	0.18075 (19)	0.0214 (4)
H20	0.5391	0.6411	0.1286	0.026*
C21	0.60615 (11)	0.7002 (2)	0.28224 (19)	0.0234 (5)
H21	0.6305	0.6228	0.2990	0.028*
C22	0.45526 (11)	0.84073 (19)	0.05346 (19)	0.0209 (4)
C23	0.37799 (11)	0.7442 (2)	−0.1100 (2)	0.0265 (5)
H23A	0.3908	0.8002	−0.1768	0.032*
H23B	0.3347	0.7788	−0.0767	0.032*
C24	0.36159 (12)	0.6163 (2)	−0.1613 (2)	0.0281 (5)
H24A	0.3206	0.6204	−0.2286	0.042*
H24B	0.3488	0.5616	−0.0945	0.042*
H24C	0.4046	0.5830	−0.1944	0.042*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0265 (8)	0.0202 (8)	0.0271 (8)	−0.0029 (6)	−0.0030 (7)	0.0048 (6)
O2	0.0308 (8)	0.0244 (8)	0.0291 (8)	0.0063 (7)	−0.0075 (7)	0.0009 (7)
O3	0.0216 (7)	0.0233 (8)	0.0235 (8)	0.0036 (6)	−0.0069 (6)	−0.0009 (6)
N1	0.0198 (8)	0.0244 (9)	0.0225 (9)	0.0007 (7)	0.0031 (7)	0.0006 (8)
C1	0.0218 (10)	0.0195 (10)	0.0202 (10)	0.0052 (8)	0.0057 (8)	0.0059 (8)
C2	0.0173 (9)	0.0200 (10)	0.0187 (10)	0.0001 (8)	0.0031 (8)	0.0001 (8)
C3	0.0162 (9)	0.0229 (10)	0.0143 (9)	0.0016 (8)	−0.0008 (8)	0.0021 (8)
C4	0.0165 (9)	0.0206 (10)	0.0178 (10)	0.0008 (8)	0.0023 (8)	0.0009 (8)
C5	0.0173 (9)	0.0229 (11)	0.0191 (10)	−0.0008 (8)	0.0011 (8)	−0.0032 (8)
C6	0.0154 (9)	0.0273 (11)	0.0173 (10)	0.0025 (8)	0.0004 (8)	0.0000 (9)
C7	0.0294 (12)	0.0291 (12)	0.0286 (12)	−0.0085 (9)	0.0037 (10)	0.0017 (10)
C8	0.0252 (10)	0.0193 (10)	0.0204 (10)	−0.0026 (8)	0.0000 (8)	0.0017 (8)
C9	0.0393 (13)	0.0220 (11)	0.0273 (12)	−0.0012 (10)	0.0047 (10)	−0.0015 (9)
C10	0.0351 (12)	0.0253 (12)	0.0275 (12)	−0.0087 (10)	−0.0080 (10)	0.0024 (10)
C11	0.0201 (10)	0.0191 (10)	0.0192 (10)	0.0004 (8)	0.0002 (8)	−0.0015 (8)
C12	0.0262 (11)	0.0220 (11)	0.0280 (12)	−0.0025 (9)	0.0031 (9)	0.0009 (9)
C13	0.0309 (11)	0.0232 (11)	0.0232 (11)	0.0051 (9)	0.0023 (9)	−0.0025 (9)
C14	0.0269 (11)	0.0202 (11)	0.0254 (11)	0.0022 (9)	−0.0024 (9)	0.0009 (9)
C15	0.0212 (10)	0.0212 (11)	0.0235 (11)	−0.0011 (8)	0.0039 (8)	−0.0020 (9)
C16	0.0170 (9)	0.0283 (12)	0.0184 (10)	0.0001 (8)	0.0014 (8)	0.0009 (9)
C17	0.0216 (10)	0.0247 (11)	0.0238 (11)	−0.0014 (9)	0.0013 (9)	−0.0008 (9)
C18	0.0226 (10)	0.0227 (11)	0.0227 (11)	0.0021 (8)	0.0012 (9)	0.0015 (9)
C19	0.0187 (10)	0.0239 (11)	0.0174 (10)	0.0028 (8)	0.0004 (8)	0.0021 (8)
C20	0.0205 (10)	0.0228 (11)	0.0204 (10)	−0.0005 (8)	0.0016 (8)	0.0003 (9)
C21	0.0216 (10)	0.0241 (11)	0.0238 (11)	0.0060 (9)	0.0004 (8)	0.0039 (9)
C22	0.0194 (10)	0.0232 (11)	0.0198 (10)	0.0001 (8)	0.0012 (8)	0.0020 (9)
C23	0.0240 (11)	0.0295 (12)	0.0231 (11)	0.0018 (9)	−0.0082 (9)	0.0016 (9)
C24	0.0261 (11)	0.0306 (12)	0.0271 (12)	−0.0001 (10)	0.0012 (9)	−0.0006 (10)

Geometric parameters (Å, º) top

O1—C1	1.355 (2)	C11—C14	1.531 (3)
O1—H1	0.866 (10)	C11—C13	1.537 (3)
O2—C22	1.207 (2)	C11—C12	1.537 (3)
O3—C22	1.346 (2)	C12—H12A	0.9800
O3—C23	1.450 (2)	C12—H12B	0.9800
N1—C15	1.273 (3)	C12—H12C	0.9800
N1—C16	1.428 (3)	C13—H13A	0.9800
C1—C6	1.406 (3)	C13—H13B	0.9800
C1—C2	1.410 (3)	C13—H13C	0.9800
C2—C3	1.397 (3)	C14—H14A	0.9800
C2—C8	1.535 (3)	C14—H14B	0.9800
C3—C4	1.402 (3)	C14—H14C	0.9800
C3—H3	0.9500	C15—H15	0.9500
C4—C5	1.389 (3)	C16—C17	1.381 (3)
C4—C11	1.529 (3)	C16—C21	1.399 (3)
C5—C6	1.393 (3)	C17—C18	1.379 (3)
C5—H5	0.9500	C17—H17	0.9500
C6—C15	1.465 (3)	C18—C19	1.395 (3)
C7—C8	1.540 (3)	C18—H18	0.9500
C7—H7A	0.9800	C19—C20	1.389 (3)
C7—H7B	0.9800	C19—C22	1.488 (3)
C7—H7C	0.9800	C20—C21	1.387 (3)
C8—C10	1.534 (3)	C20—H20	0.9500
C8—C9	1.539 (3)	C21—H21	0.9500
C9—H9A	0.9800	C23—C24	1.494 (3)
C9—H9B	0.9800	C23—H23A	0.9900
C9—H9C	0.9800	C23—H23B	0.9900
C10—H10A	0.9800	C24—H24A	0.9800
C10—H10B	0.9800	C24—H24B	0.9800
C10—H10C	0.9800	C24—H24C	0.9800

C1—O1—H1	106 (2)	H12A—C12—H12B	109.5
C22—O3—C23	114.99 (16)	C11—C12—H12C	109.5
C15—N1—C16	118.83 (18)	H12A—C12—H12C	109.5
O1—C1—C6	119.20 (18)	H12B—C12—H12C	109.5
O1—C1—C2	120.37 (18)	C11—C13—H13A	109.5
C6—C1—C2	120.43 (18)	C11—C13—H13B	109.5
C3—C2—C1	116.73 (18)	H13A—C13—H13B	109.5
C3—C2—C8	121.24 (17)	C11—C13—H13C	109.5
C1—C2—C8	121.96 (18)	H13A—C13—H13C	109.5
C2—C3—C4	124.26 (18)	H13B—C13—H13C	109.5
C2—C3—H3	117.9	C11—C14—H14A	109.5
C4—C3—H3	117.9	C11—C14—H14B	109.5
C5—C4—C3	116.83 (18)	H14A—C14—H14B	109.5
C5—C4—C11	120.03 (17)	C11—C14—H14C	109.5
C3—C4—C11	123.12 (17)	H14A—C14—H14C	109.5
C4—C5—C6	121.49 (19)	H14B—C14—H14C	109.5
C4—C5—H5	119.3	N1—C15—C6	122.09 (19)
C6—C5—H5	119.3	N1—C15—H15	119.0
C5—C6—C1	120.03 (18)	C6—C15—H15	119.0
C5—C6—C15	117.32 (18)	C17—C16—C21	119.51 (19)
C1—C6—C15	122.63 (19)	C17—C16—N1	117.79 (19)
C8—C7—H7A	109.5	C21—C16—N1	122.64 (19)
C8—C7—H7B	109.5	C18—C17—C16	120.3 (2)
H7A—C7—H7B	109.5	C18—C17—H17	119.8
C8—C7—H7C	109.5	C16—C17—H17	119.8
H7A—C7—H7C	109.5	C17—C18—C19	120.5 (2)
H7B—C7—H7C	109.5	C17—C18—H18	119.7
C10—C8—C2	112.00 (17)	C19—C18—H18	119.7
C10—C8—C7	107.87 (18)	C20—C19—C18	119.40 (18)
C2—C8—C7	108.92 (17)	C20—C19—C22	122.69 (19)
C10—C8—C9	106.89 (17)	C18—C19—C22	117.87 (18)
C2—C8—C9	111.03 (17)	C21—C20—C19	120.0 (2)
C7—C8—C9	110.07 (18)	C21—C20—H20	120.0
C8—C9—H9A	109.5	C19—C20—H20	120.0
C8—C9—H9B	109.5	C20—C21—C16	120.18 (19)
H9A—C9—H9B	109.5	C20—C21—H21	119.9
C8—C9—H9C	109.5	C16—C21—H21	119.9
H9A—C9—H9C	109.5	O2—C22—O3	123.23 (18)
H9B—C9—H9C	109.5	O2—C22—C19	124.17 (19)
C8—C10—H10A	109.5	O3—C22—C19	112.57 (17)
C8—C10—H10B	109.5	O3—C23—C24	107.99 (17)
H10A—C10—H10B	109.5	O3—C23—H23A	110.1
C8—C10—H10C	109.5	C24—C23—H23A	110.1
H10A—C10—H10C	109.5	O3—C23—H23B	110.1
H10B—C10—H10C	109.5	C24—C23—H23B	110.1
C4—C11—C14	112.55 (16)	H23A—C23—H23B	108.4
C4—C11—C13	108.92 (16)	C23—C24—H24A	109.5
C14—C11—C13	108.30 (16)	C23—C24—H24B	109.5
C4—C11—C12	109.85 (16)	H24A—C24—H24B	109.5
C14—C11—C12	107.53 (17)	C23—C24—H24C	109.5
C13—C11—C12	109.64 (17)	H24A—C24—H24C	109.5
C11—C12—H12A	109.5	H24B—C24—H24C	109.5
C11—C12—H12B	109.5

O1—C1—C2—C3	−175.11 (17)	C3—C4—C11—C13	−122.2 (2)
C6—C1—C2—C3	4.6 (3)	C5—C4—C11—C12	−64.1 (2)
O1—C1—C2—C8	1.8 (3)	C3—C4—C11—C12	117.6 (2)
C6—C1—C2—C8	−178.52 (18)	C16—N1—C15—C6	178.21 (17)
C1—C2—C3—C4	−1.5 (3)	C5—C6—C15—N1	−174.29 (19)
C8—C2—C3—C4	−178.36 (18)	C1—C6—C15—N1	4.0 (3)
C2—C3—C4—C5	−2.7 (3)	C15—N1—C16—C17	151.3 (2)
C2—C3—C4—C11	175.58 (19)	C15—N1—C16—C21	−31.4 (3)
C3—C4—C5—C6	3.9 (3)	C21—C16—C17—C18	3.2 (3)
C11—C4—C5—C6	−174.44 (18)	N1—C16—C17—C18	−179.46 (18)
C4—C5—C6—C1	−0.9 (3)	C16—C17—C18—C19	−0.4 (3)
C4—C5—C6—C15	177.43 (18)	C17—C18—C19—C20	−2.2 (3)
O1—C1—C6—C5	176.18 (18)	C17—C18—C19—C22	175.61 (19)
C2—C1—C6—C5	−3.5 (3)	C18—C19—C20—C21	2.0 (3)
O1—C1—C6—C15	−2.1 (3)	C22—C19—C20—C21	−175.68 (18)
C2—C1—C6—C15	178.18 (18)	C19—C20—C21—C16	0.8 (3)
C3—C2—C8—C10	−9.4 (3)	C17—C16—C21—C20	−3.4 (3)
C1—C2—C8—C10	173.86 (19)	N1—C16—C21—C20	179.43 (18)
C3—C2—C8—C7	109.8 (2)	C23—O3—C22—O2	0.8 (3)
C1—C2—C8—C7	−66.9 (2)	C23—O3—C22—C19	178.95 (17)
C3—C2—C8—C9	−128.8 (2)	C20—C19—C22—O2	177.1 (2)
C1—C2—C8—C9	54.5 (2)	C18—C19—C22—O2	−0.6 (3)
C5—C4—C11—C14	176.14 (18)	C20—C19—C22—O3	−1.0 (3)
C3—C4—C11—C14	−2.1 (3)	C18—C19—C22—O3	−178.74 (18)
C5—C4—C11—C13	56.0 (2)	C22—O3—C23—C24	−173.52 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.87 (1)	1.80 (2)	2.609 (2)	154 (3)

Experimental details

Crystal data
Chemical formula	C₂₄H₃₁NO₃
M_r	381.50
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	18.4789 (18), 10.7194 (11), 10.7768 (10)
β (°)	97.437 (2)
V (Å³)	2116.7 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.05 × 0.05

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	19941, 4855, 3123
R_int	0.065
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.142, 1.01
No. of reflections	4855
No. of parameters	257
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.64, −0.26

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.87 (1)	1.80 (2)	2.609 (2)	154 (3)

Acknowledgements

We thank the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sliwa, M., Spangenberg, A., Metivier, R., Letard, S., Nakatani, K. & Yu, P. (2008). Res. Chem. Intermed. 34, 181–190. Web of Science CrossRef CAS Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar