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

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

doi:10.1107/S1600536810040742

organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page o2916

https://doi.org/10.1107/S1600536810040742

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Ethyl 4-[(3,5-di-tert-butyl-2-hydroxybenzyl)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 6 October 2010; accepted 11 October 2010; online 23 October 2010)

The title amine, C₂₄H₃₃NO₃, has two substituted aromatic rings at either end of the –CH₂NH– linkage [C_aryl–CH₂–NH–C_aryl torsion angle = 77.4 (3)°]. The amino and hydroxy groups are hydrogen-bond donors to the carbonyl O atom of an adjacent molecule. These hydrogen bonds give rise to a chain that runs along the b axis. One of the tert-butyl groups is disordered over two positions with a site-occupation factor of 0.834 (6) for the major occupied site.

Related literature

For the structure of the Schiff-base reactant, see: Shakir et al. (2010 ).

Experimental

Crystal data

C₂₄H₃₃NO₃
M_r = 383.51
Monoclinic, P 2₁ /c
a = 17.788 (3) Å
b = 8.9872 (14) Å
c = 14.235 (2) Å
β = 101.414 (2)°
V = 2230.7 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 100 K
0.30 × 0.10 × 0.03 mm

Data collection

Bruker SMART APEX diffractometer
17094 measured reflections
3928 independent reflections
2428 reflections with I > 2σ(I)
R_int = 0.092

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.154
S = 1.03
3928 reflections
283 parameters
45 restraints
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯O2ⁱ	0.84	2.13	2.909 (3)	154
N1—H1n⋯O2ⁱ	0.88	2.07	2.827 (3)	143
Symmetry code: (i) x, y+1, z.

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/S1600536810040742/bt5371sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810040742/bt5371Isup2.hkl

checkCIF report

Comment top

The Schiff base, ethyl 4-(di-3,5-tert-butyl-2-hydroxybenzylideneamino)benzoate, is an intensely orange-colored compound whose color can be attributed to the azomethine double-bond; in the crystal structure, the two aromatic rings are aligned at 24.9 (1) ° (Shakir et al., 2010). The reduction of this compound affords the title colorless compound (Scheme I, Fig. 1), which is a secondary amine. The amino and hydroxy groups are hydrogen-bond donors to the carbonyl oxygen atom of an adjacent molecule; the hydrogen bonds give rise to a chain that runs along the b-axis. One of the tert-butyl groups is disordered over two positions with respect to the methyl units in an 83.6 (6):16.4 (6) ratio.

Related literature top

For the structure of the Schiff-base reactant, see: Shakir et al. (2010).

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. The compound (0.5 g) was dissolved in methanol-THF (1:1) (20 ml). The solution was cooled to 273 K and three equivalents of sodium tetraborate were added. The mixture was stirred for 4 h until the orange color was discharged. The mixture was filtered and the solvent evaporated. The colorless compound was recrystallized from a hexane-ethanol mixure (yield 90%).

Structure description top

For the structure of the Schiff-base reactant, see: Shakir et al. (2010).

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. Anisotropic displacement ellipsoid plot (Barbour, 2001) of C₂₄H₃₃NO₃ at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder in one of the tert-butyl groups is not shown.
	Fig. 2. Hydrogen-bonded chain motif.

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

Crystal data top

C₂₄H₃₃NO₃	F(000) = 832
M_r = 383.51	D_x = 1.142 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1466 reflections
a = 17.788 (3) Å	θ = 2.1–21.3°
b = 8.9872 (14) Å	µ = 0.07 mm⁻¹
c = 14.235 (2) Å	T = 100 K
β = 101.414 (2)°	Prism, colorless
V = 2230.7 (6) Å³	0.30 × 0.10 × 0.03 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	2428 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.092
Graphite monochromator	θ_max = 25.0°, θ_min = 2.3°
ω scans	h = −20→21
17094 measured reflections	k = −10→10
3928 independent reflections	l = −16→16

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.058	H-atom parameters constrained
wR(F²) = 0.154	w = 1/[σ²(F_o²) + (0.0662P)² + 0.7154P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
3928 reflections	Δρ_max = 0.24 e Å⁻³
283 parameters	Δρ_min = −0.23 e Å⁻³
45 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0079 (12)

Crystal data top

C₂₄H₃₃NO₃	V = 2230.7 (6) Å³
M_r = 383.51	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.788 (3) Å	µ = 0.07 mm⁻¹
b = 8.9872 (14) Å	T = 100 K
c = 14.235 (2) Å	0.30 × 0.10 × 0.03 mm
β = 101.414 (2)°

Data collection top

Bruker SMART APEX diffractometer	2428 reflections with I > 2σ(I)
17094 measured reflections	R_int = 0.092
3928 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	45 restraints
wR(F²) = 0.154	H-atom parameters constrained
S = 1.03	Δρ_max = 0.24 e Å⁻³
3928 reflections	Δρ_min = −0.23 e Å⁻³
283 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.32463 (11)	0.7157 (2)	0.42898 (14)	0.0281 (5)
H1O	0.3613	0.7145	0.3998	0.042*
O2	0.46605 (11)	−0.2040 (2)	0.36814 (13)	0.0257 (5)
O3	0.58429 (11)	−0.1107 (2)	0.41969 (13)	0.0237 (5)
N1	0.41764 (13)	0.5020 (2)	0.31779 (16)	0.0223 (6)
H1N	0.4497	0.5690	0.3479	0.027*
C1	0.26841 (16)	0.6193 (3)	0.38515 (19)	0.0206 (6)
C2	0.20301 (16)	0.6027 (3)	0.4259 (2)	0.0224 (7)
C3	0.14725 (16)	0.5024 (3)	0.3809 (2)	0.0246 (7)
H3	0.1028	0.4890	0.4076	0.029*
C4	0.15296 (16)	0.4208 (3)	0.2993 (2)	0.0227 (7)
C5	0.21844 (16)	0.4441 (3)	0.2617 (2)	0.0227 (7)
H5	0.2236	0.3920	0.2052	0.027*
C6	0.27635 (15)	0.5401 (3)	0.30322 (19)	0.0197 (6)
C7	0.19398 (17)	0.6857 (3)	0.5172 (2)	0.0272 (7)
C8	0.11681 (17)	0.6522 (4)	0.5457 (2)	0.0388 (8)
H8A	0.1126	0.5451	0.5564	0.058*
H8B	0.0748	0.6841	0.4942	0.058*
H8C	0.1138	0.7061	0.6047	0.058*
C9	0.25655 (17)	0.6366 (4)	0.6014 (2)	0.0332 (8)
H9A	0.2537	0.5286	0.6097	0.050*
H9B	0.2490	0.6867	0.6600	0.050*
H9C	0.3070	0.6631	0.5885	0.050*
C10	0.1981 (2)	0.8544 (3)	0.5028 (2)	0.0399 (9)
H10A	0.2468	0.8797	0.4842	0.060*
H10B	0.1949	0.9054	0.5627	0.060*
H10C	0.1554	0.8860	0.4522	0.060*
C11	0.09420 (17)	0.3034 (3)	0.2554 (2)	0.0365 (8)
C12	0.0664 (3)	0.3407 (7)	0.1489 (3)	0.077 (2)	0.834 (6)
H12A	0.0275	0.2683	0.1199	0.115*	0.834 (6)
H12B	0.1099	0.3368	0.1161	0.115*	0.834 (6)
H12C	0.0442	0.4408	0.1428	0.115*	0.834 (6)
C13	0.1347 (3)	0.1529 (4)	0.2641 (4)	0.0600 (17)	0.834 (6)
H13A	0.0980	0.0750	0.2377	0.090*	0.834 (6)
H13B	0.1557	0.1318	0.3317	0.090*	0.834 (6)
H13C	0.1765	0.1552	0.2284	0.090*	0.834 (6)
C14	0.0263 (2)	0.2976 (5)	0.3027 (4)	0.0452 (13)	0.834 (6)
H14A	−0.0094	0.2209	0.2719	0.068*	0.834 (6)
H14B	0.0005	0.3944	0.2964	0.068*	0.834 (6)
H14C	0.0433	0.2735	0.3707	0.068*	0.834 (6)
C12'	0.1079 (13)	0.210 (2)	0.1736 (14)	0.048 (7)	0.166 (6)
H12D	0.1621	0.2163	0.1694	0.073*	0.166 (6)
H12E	0.0761	0.2472	0.1139	0.073*	0.166 (6)
H12F	0.0944	0.1068	0.1839	0.073*	0.166 (6)
C13'	0.0927 (15)	0.184 (2)	0.3315 (15)	0.074 (9)	0.166 (6)
H13D	0.1373	0.1185	0.3355	0.111*	0.166 (6)
H13E	0.0456	0.1248	0.3140	0.111*	0.166 (6)
H13F	0.0941	0.2313	0.3938	0.111*	0.166 (6)
C14'	0.0130 (7)	0.361 (2)	0.2415 (18)	0.048 (7)	0.166 (6)
H14D	−0.0041	0.3589	0.3028	0.072*	0.166 (6)
H14E	−0.0208	0.2991	0.1948	0.072*	0.166 (6)
H14F	0.0114	0.4641	0.2180	0.072*	0.166 (6)
C15	0.34660 (15)	0.5559 (3)	0.25896 (19)	0.0225 (7)
H15A	0.3374	0.5013	0.1974	0.027*
H15B	0.3531	0.6623	0.2445	0.027*
C16	0.43888 (16)	0.3562 (3)	0.33031 (19)	0.0203 (6)
C17	0.51327 (15)	0.3219 (3)	0.37876 (19)	0.0205 (6)
H17	0.5482	0.4004	0.4004	0.025*
C18	0.53670 (16)	0.1770 (3)	0.39565 (19)	0.0204 (6)
H18	0.5876	0.1565	0.4282	0.024*
C19	0.48608 (16)	0.0590 (3)	0.36514 (19)	0.0202 (6)
C20	0.41230 (16)	0.0918 (3)	0.31703 (19)	0.0220 (7)
H20	0.3774	0.0130	0.2960	0.026*
C21	0.38877 (16)	0.2380 (3)	0.29915 (18)	0.0208 (6)
H21	0.3382	0.2581	0.2654	0.025*
C22	0.50943 (15)	−0.0962 (3)	0.38371 (18)	0.0194 (6)
C23	0.61300 (17)	−0.2598 (3)	0.4479 (2)	0.0245 (7)
H23A	0.6072	−0.3259	0.3912	0.029*
H23B	0.5846	−0.3037	0.4944	0.029*
C24	0.69625 (17)	−0.2403 (3)	0.4929 (2)	0.0320 (8)
H24A	0.7188	−0.3374	0.5133	0.048*
H24B	0.7009	−0.1744	0.5486	0.048*
H24C	0.7234	−0.1964	0.4460	0.048*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0285 (12)	0.0281 (11)	0.0296 (12)	−0.0076 (9)	0.0102 (9)	−0.0064 (9)
O2	0.0288 (12)	0.0204 (11)	0.0285 (11)	−0.0036 (9)	0.0072 (9)	−0.0018 (9)
O3	0.0254 (11)	0.0184 (10)	0.0271 (11)	0.0027 (8)	0.0049 (9)	0.0050 (8)
N1	0.0229 (13)	0.0186 (13)	0.0255 (13)	0.0000 (10)	0.0045 (11)	−0.0029 (10)
C1	0.0232 (16)	0.0138 (14)	0.0229 (15)	0.0011 (12)	0.0001 (12)	−0.0007 (12)
C2	0.0201 (16)	0.0216 (15)	0.0254 (15)	0.0033 (12)	0.0044 (12)	0.0012 (12)
C3	0.0204 (16)	0.0246 (16)	0.0295 (17)	0.0006 (12)	0.0068 (13)	0.0009 (13)
C4	0.0191 (16)	0.0217 (15)	0.0252 (16)	0.0030 (12)	−0.0009 (13)	−0.0025 (12)
C5	0.0265 (17)	0.0197 (15)	0.0209 (15)	0.0051 (12)	0.0025 (13)	−0.0006 (12)
C6	0.0225 (16)	0.0176 (14)	0.0189 (14)	0.0036 (12)	0.0035 (12)	0.0029 (12)
C7	0.0275 (17)	0.0290 (17)	0.0277 (16)	0.0003 (13)	0.0114 (14)	−0.0037 (13)
C8	0.0319 (19)	0.051 (2)	0.0372 (19)	−0.0004 (16)	0.0151 (16)	−0.0107 (16)
C9	0.0332 (19)	0.0406 (19)	0.0275 (17)	−0.0082 (15)	0.0101 (14)	−0.0066 (15)
C10	0.047 (2)	0.0295 (18)	0.047 (2)	0.0008 (15)	0.0194 (17)	−0.0112 (16)
C11	0.0273 (18)	0.0364 (19)	0.044 (2)	−0.0023 (15)	0.0038 (16)	−0.0094 (16)
C12	0.063 (3)	0.113 (5)	0.047 (3)	−0.052 (3)	−0.009 (2)	−0.010 (3)
C13	0.045 (3)	0.033 (2)	0.106 (4)	−0.014 (2)	0.025 (3)	−0.032 (3)
C14	0.028 (2)	0.042 (3)	0.068 (3)	−0.0133 (19)	0.016 (2)	−0.016 (2)
C12'	0.043 (10)	0.047 (10)	0.053 (10)	−0.007 (8)	0.004 (8)	−0.026 (8)
C13'	0.078 (12)	0.063 (11)	0.078 (12)	−0.014 (9)	0.007 (9)	−0.005 (9)
C14'	0.046 (10)	0.050 (10)	0.048 (10)	−0.009 (8)	0.007 (8)	−0.012 (8)
C15	0.0259 (17)	0.0199 (15)	0.0218 (15)	0.0045 (12)	0.0047 (13)	0.0009 (12)
C16	0.0259 (16)	0.0195 (15)	0.0174 (14)	0.0004 (12)	0.0090 (12)	−0.0002 (12)
C17	0.0234 (16)	0.0173 (14)	0.0220 (15)	−0.0040 (12)	0.0075 (13)	−0.0046 (12)
C18	0.0201 (15)	0.0225 (15)	0.0191 (14)	0.0006 (12)	0.0054 (12)	−0.0018 (12)
C19	0.0218 (16)	0.0220 (15)	0.0181 (14)	0.0009 (12)	0.0072 (12)	−0.0004 (12)
C20	0.0244 (16)	0.0193 (15)	0.0234 (15)	−0.0033 (12)	0.0075 (13)	−0.0012 (12)
C21	0.0209 (15)	0.0245 (16)	0.0177 (15)	0.0000 (12)	0.0058 (12)	−0.0026 (12)
C22	0.0193 (16)	0.0228 (15)	0.0176 (14)	−0.0010 (13)	0.0070 (12)	−0.0016 (12)
C23	0.0359 (18)	0.0181 (15)	0.0212 (15)	0.0056 (13)	0.0095 (13)	0.0042 (12)
C24	0.0344 (19)	0.0292 (17)	0.0323 (18)	0.0076 (14)	0.0065 (15)	0.0098 (14)

Geometric parameters (Å, º) top

O1—C1	1.376 (3)	C12—H12A	0.9800
O1—H1O	0.8400	C12—H12B	0.9800
O2—C22	1.231 (3)	C12—H12C	0.9800
O3—C22	1.335 (3)	C13—H13A	0.9800
O3—C23	1.462 (3)	C13—H13B	0.9800
N1—C16	1.366 (3)	C13—H13C	0.9800
N1—C15	1.454 (3)	C14—H14A	0.9800
N1—H1N	0.8800	C14—H14B	0.9800
C1—C6	1.397 (4)	C14—H14C	0.9800
C1—C2	1.407 (4)	C12'—H12D	0.9800
C2—C3	1.398 (4)	C12'—H12E	0.9800
C2—C7	1.534 (4)	C12'—H12F	0.9800
C3—C4	1.395 (4)	C13'—H13D	0.9800
C3—H3	0.9500	C13'—H13E	0.9800
C4—C5	1.391 (4)	C13'—H13F	0.9800
C4—C11	1.529 (4)	C14'—H14D	0.9800
C5—C6	1.384 (4)	C14'—H14E	0.9800
C5—H5	0.9500	C14'—H14F	0.9800
C6—C15	1.513 (4)	C15—H15A	0.9900
C7—C10	1.534 (4)	C15—H15B	0.9900
C7—C9	1.531 (4)	C16—C17	1.400 (4)
C7—C8	1.536 (4)	C16—C21	1.401 (4)
C8—H8A	0.9800	C17—C18	1.374 (4)
C8—H8B	0.9800	C17—H17	0.9500
C8—H8C	0.9800	C18—C19	1.403 (4)
C9—H9A	0.9800	C18—H18	0.9500
C9—H9B	0.9800	C19—C20	1.387 (4)
C9—H9C	0.9800	C19—C22	1.465 (4)
C10—H10A	0.9800	C20—C21	1.387 (4)
C10—H10B	0.9800	C20—H20	0.9500
C10—H10C	0.9800	C21—H21	0.9500
C11—C12'	1.491 (9)	C23—C24	1.503 (4)
C11—C14	1.495 (5)	C23—H23A	0.9900
C11—C14'	1.511 (9)	C23—H23B	0.9900
C11—C13	1.526 (5)	C24—H24A	0.9800
C11—C13'	1.531 (10)	C24—H24B	0.9800
C11—C12	1.535 (5)	C24—H24C	0.9800

C1—O1—H1O	109.5	H13A—C13—H13B	109.5
C22—O3—C23	117.5 (2)	C11—C13—H13C	109.5
C16—N1—C15	125.5 (2)	H13A—C13—H13C	109.5
C16—N1—H1N	117.2	H13B—C13—H13C	109.5
C15—N1—H1N	117.2	C11—C14—H14A	109.5
O1—C1—C6	121.0 (3)	C11—C14—H14B	109.5
O1—C1—C2	117.8 (2)	H14A—C14—H14B	109.5
C6—C1—C2	121.2 (2)	C11—C14—H14C	109.5
C3—C2—C1	116.7 (3)	H14A—C14—H14C	109.5
C3—C2—C7	121.1 (3)	H14B—C14—H14C	109.5
C1—C2—C7	122.1 (2)	C11—C12'—H12D	109.5
C4—C3—C2	123.9 (3)	C11—C12'—H12E	109.5
C4—C3—H3	118.0	H12D—C12'—H12E	109.5
C2—C3—H3	118.0	C11—C12'—H12F	109.5
C5—C4—C3	116.5 (2)	H12D—C12'—H12F	109.5
C5—C4—C11	120.2 (3)	H12E—C12'—H12F	109.5
C3—C4—C11	123.2 (3)	C11—C13'—H13D	109.5
C6—C5—C4	122.6 (3)	C11—C13'—H13E	109.5
C6—C5—H5	118.7	H13D—C13'—H13E	109.5
C4—C5—H5	118.7	C11—C13'—H13F	109.5
C5—C6—C1	119.0 (3)	H13D—C13'—H13F	109.5
C5—C6—C15	119.1 (2)	H13E—C13'—H13F	109.5
C1—C6—C15	121.9 (2)	C11—C14'—H14D	109.5
C10—C7—C9	110.0 (3)	C11—C14'—H14E	109.5
C10—C7—C8	107.4 (3)	H14D—C14'—H14E	109.5
C9—C7—C8	106.6 (2)	C11—C14'—H14F	109.5
C10—C7—C2	110.6 (2)	H14D—C14'—H14F	109.5
C9—C7—C2	110.0 (2)	H14E—C14'—H14F	109.5
C8—C7—C2	112.2 (2)	N1—C15—C6	115.1 (2)
C7—C8—H8A	109.5	N1—C15—H15A	108.5
C7—C8—H8B	109.5	C6—C15—H15A	108.5
H8A—C8—H8B	109.5	N1—C15—H15B	108.5
C7—C8—H8C	109.5	C6—C15—H15B	108.5
H8A—C8—H8C	109.5	H15A—C15—H15B	107.5
H8B—C8—H8C	109.5	N1—C16—C17	119.0 (2)
C7—C9—H9A	109.5	N1—C16—C21	123.0 (2)
C7—C9—H9B	109.5	C17—C16—C21	118.0 (2)
H9A—C9—H9B	109.5	C18—C17—C16	121.3 (2)
C7—C9—H9C	109.5	C18—C17—H17	119.4
H9A—C9—H9C	109.5	C16—C17—H17	119.4
H9B—C9—H9C	109.5	C17—C18—C19	120.6 (3)
C7—C10—H10A	109.5	C17—C18—H18	119.7
C7—C10—H10B	109.5	C19—C18—H18	119.7
H10A—C10—H10B	109.5	C20—C19—C18	118.6 (2)
C7—C10—H10C	109.5	C20—C19—C22	119.9 (2)
H10A—C10—H10C	109.5	C18—C19—C22	121.5 (2)
H10B—C10—H10C	109.5	C19—C20—C21	120.9 (3)
C12'—C11—C14'	113.0 (13)	C19—C20—H20	119.5
C14—C11—C13	110.1 (3)	C21—C20—H20	119.5
C12'—C11—C13'	100.8 (15)	C20—C21—C16	120.7 (3)
C14'—C11—C13'	100.6 (13)	C20—C21—H21	119.7
C12'—C11—C4	120.1 (9)	C16—C21—H21	119.7
C14—C11—C4	112.8 (3)	O2—C22—O3	122.3 (2)
C14'—C11—C4	111.9 (9)	O2—C22—C19	124.9 (2)
C13—C11—C4	107.7 (3)	O3—C22—C19	112.8 (2)
C13'—C11—C4	107.6 (10)	O3—C23—C24	105.7 (2)
C14—C11—C12	108.7 (3)	O3—C23—H23A	110.6
C13—C11—C12	109.1 (4)	C24—C23—H23A	110.6
C4—C11—C12	108.3 (3)	O3—C23—H23B	110.6
C11—C12—H12A	109.5	C24—C23—H23B	110.6
C11—C12—H12B	109.5	H23A—C23—H23B	108.7
H12A—C12—H12B	109.5	C23—C24—H24A	109.5
C11—C12—H12C	109.5	C23—C24—H24B	109.5
H12A—C12—H12C	109.5	H24A—C24—H24B	109.5
H12B—C12—H12C	109.5	C23—C24—H24C	109.5
C11—C13—H13A	109.5	H24A—C24—H24C	109.5
C11—C13—H13B	109.5	H24B—C24—H24C	109.5

O1—C1—C2—C3	−179.0 (2)	C5—C4—C11—C13	60.4 (4)
C6—C1—C2—C3	0.7 (4)	C3—C4—C11—C13	−115.5 (4)
O1—C1—C2—C7	−1.2 (4)	C5—C4—C11—C13'	116.0 (12)
C6—C1—C2—C7	178.5 (2)	C3—C4—C11—C13'	−59.9 (12)
C1—C2—C3—C4	−0.5 (4)	C5—C4—C11—C12	−57.5 (4)
C7—C2—C3—C4	−178.3 (3)	C3—C4—C11—C12	126.6 (4)
C2—C3—C4—C5	−0.6 (4)	C16—N1—C15—C6	77.4 (3)
C2—C3—C4—C11	175.5 (3)	C5—C6—C15—N1	−113.9 (3)
C3—C4—C5—C6	1.5 (4)	C1—C6—C15—N1	65.8 (3)
C11—C4—C5—C6	−174.7 (3)	C15—N1—C16—C17	171.6 (2)
C4—C5—C6—C1	−1.3 (4)	C15—N1—C16—C21	−10.2 (4)
C4—C5—C6—C15	178.4 (2)	N1—C16—C17—C18	178.1 (3)
O1—C1—C6—C5	179.8 (2)	C21—C16—C17—C18	−0.1 (4)
C2—C1—C6—C5	0.2 (4)	C16—C17—C18—C19	−0.5 (4)
O1—C1—C6—C15	0.1 (4)	C17—C18—C19—C20	0.5 (4)
C2—C1—C6—C15	−179.6 (2)	C17—C18—C19—C22	−179.0 (2)
C3—C2—C7—C10	−123.6 (3)	C18—C19—C20—C21	0.1 (4)
C1—C2—C7—C10	58.7 (3)	C22—C19—C20—C21	179.6 (3)
C3—C2—C7—C9	114.7 (3)	C19—C20—C21—C16	−0.7 (4)
C1—C2—C7—C9	−63.1 (3)	N1—C16—C21—C20	−177.4 (3)
C3—C2—C7—C8	−3.8 (4)	C17—C16—C21—C20	0.7 (4)
C1—C2—C7—C8	178.5 (3)	C23—O3—C22—O2	−4.9 (4)
C5—C4—C11—C12'	1.7 (13)	C23—O3—C22—C19	175.4 (2)
C3—C4—C11—C12'	−174.2 (12)	C20—C19—C22—O2	−7.5 (4)
C5—C4—C11—C14	−177.9 (3)	C18—C19—C22—O2	172.0 (3)
C3—C4—C11—C14	6.2 (4)	C20—C19—C22—O3	172.2 (2)
C5—C4—C11—C14'	−134.4 (11)	C18—C19—C22—O3	−8.3 (4)
C3—C4—C11—C14'	49.7 (11)	C22—O3—C23—C24	−175.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···O2ⁱ	0.84	2.13	2.909 (3)	154
N1—H1n···O2ⁱ	0.88	2.07	2.827 (3)	143

Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₂₄H₃₃NO₃
M_r	383.51
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	17.788 (3), 8.9872 (14), 14.235 (2)
β (°)	101.414 (2)
V (Å³)	2230.7 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.30 × 0.10 × 0.03

Data collection
Diffractometer	Bruker SMART APEX
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	17094, 3928, 2428
R_int	0.092
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.154, 1.03
No. of reflections	3928
No. of parameters	283
No. of restraints	45
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.23

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—H1o···O2ⁱ	0.84	2.13	2.909 (3)	154
N1—H1n···O2ⁱ	0.88	2.07	2.827 (3)	143

Symmetry code: (i) x, y+1, z.

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
Shakir, R. M., Ariffin, A. & Ng, S. W. (2010). Acta Cryst. E66, o2915. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar