4,4′-Diethyl-2,2′-[(N-cyclo­hexyl­imino)­bis­(methyl­ene)]diphenol

Wattanathana, W.; Veranitisagul, C.; Kaewvilai, A.; Laobuthee, A.; Koonsaeng, N.

doi:10.1107/S1600536812040342

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 10| October 2012| Page o3050

https://doi.org/10.1107/S1600536812040342

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4,4′-Diethyl-2,2′-[(N-cyclohexylimino)bis(methylene)]diphenol

Worawat Wattanathana,^a Chatchai Veranitisagul,^b Attaphon Kaewvilai,^c Apirat Laobuthee ^c and Nattamon Koonsaeng ^a ^*

^aDepartment of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, Thailand, ^bDepartment of Materials and Metallurgical Engineering, Faculty of Engineering, Rajamangala University of Technology Thanyaburi, Pathumthani 12110, Thailand, and ^cDepartment of Materials Engineering, Faculty of Engineering and Center of Advanced Studies in Industrial Technology, Kasetsart University, Bangkok 10900, Thailand
^*Correspondence e-mail: fscinmk@ku.ac.th

(Received 7 September 2012; accepted 24 September 2012; online 29 September 2012)

The title compound, C₂₄H₃₃NO₂, exhibits an intramolecular hydrogen bond between a phenol –OH group and the N atom. In the crystal, molecules are connected by pairs of O—H⋯O hydrogen bonds.

Related literature

For details of the synthesis of N,N-bis(2-hydroxybenzyl)alkylamines, see: Laobuthee et al. (2003 ). For their metal-responsive properties, see: Veranitisagul et al. (2011 ). For their use in the synthesis of macrocyclic molecules, see: Rungsimanon et al. (2008 ).

Experimental

Crystal data

C₂₄H₃₃NO₂
M_r = 367.51
Triclinic, $[P \overline 1]$
a = 9.4224 (12) Å
b = 10.3799 (16) Å
c = 11.8143 (18) Å
α = 82.140 (4)°
β = 73.960 (4)°
γ = 81.676 (4)°
V = 1093.1 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 296 K
0.90 × 0.44 × 0.24 mm

Data collection

Bruker APEXII CCD diffractometer
8721 measured reflections
5350 independent reflections
3648 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.185
S = 1.12
5350 reflections
252 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 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—H1⋯O2	0.94 (3)	2.52 (2)	3.156 (2)	124.8 (18)
O1—H1⋯N	0.94 (3)	1.79 (3)	2.6352 (19)	147.8 (19)
O2—H2⋯O1ⁱ	0.88 (3)	1.84 (3)	2.708 (2)	168 (3)
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812040342/gg2100sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812040342/gg2100Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812040342/gg2100Isup3.cml

checkCIF report

Related literature top

For details of the synthesis of N,N-bis(2-hydroxybenzyl)alkylamines, see: Laobuthee et al. (2003). For their metal-responsive properties, see: Veranitisagul et al. (2011). For their use in the synthesis of macrocyclic molecules, see: Rungsimanon et al. (2008).

Experimental top

The preparation of the title compound was reported elsewhere (Laobuthee et al., 2003). Colorless blocks were recrystallized from 2-propanol solution.

Structure description top

For details of the synthesis of N,N-bis(2-hydroxybenzyl)alkylamines, see: Laobuthee et al. (2003). For their metal-responsive properties, see: Veranitisagul et al. (2011). For their use in the synthesis of macrocyclic molecules, see: Rungsimanon et al. (2008).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008 and publCIF (Westrip, 2010).

Figures top

Fig. 1. Molecular structure of the title compound (arbitrary spheres for the H atoms).

4,4'-Diethyl-2,2'-[(N-cyclohexylimino)bis(methylene)]diphenol top

Crystal data top

C₂₄H₃₃NO₂	Z = 2
M_r = 367.51	F(000) = 400.0
Triclinic, P1	D_x = 1.117 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.4224 (12) Å	Cell parameters from 3314 reflections
b = 10.3799 (16) Å	θ = 2.6–28.2°
c = 11.8143 (18) Å	µ = 0.07 mm⁻¹
α = 82.140 (4)°	T = 296 K
β = 73.960 (4)°	Block, colourless
γ = 81.676 (4)°	0.90 × 0.44 × 0.24 mm
V = 1093.1 (3) Å³

Data collection top

Bruker APEXII CCD diffractometer	3648 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.022
Graphite monochromator	θ_max = 28.2°, θ_min = 1.8°
φ and ω scans	h = −12→12
8721 measured reflections	k = −13→13
5350 independent reflections	l = −15→15

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.185	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ²(F_o²) + (0.085P)² + 0.1411P] where P = (F_o² + 2F_c²)/3
5350 reflections	(Δ/σ)_max < 0.001
252 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₄H₃₃NO₂	γ = 81.676 (4)°
M_r = 367.51	V = 1093.1 (3) Å³
Triclinic, P1	Z = 2
a = 9.4224 (12) Å	Mo Kα radiation
b = 10.3799 (16) Å	µ = 0.07 mm⁻¹
c = 11.8143 (18) Å	T = 296 K
α = 82.140 (4)°	0.90 × 0.44 × 0.24 mm
β = 73.960 (4)°

Data collection top

Bruker APEXII CCD diffractometer	3648 reflections with I > 2σ(I)
8721 measured reflections	R_int = 0.022
5350 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	0 restraints
wR(F²) = 0.185	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	Δρ_max = 0.27 e Å⁻³
5350 reflections	Δρ_min = −0.23 e Å⁻³
252 parameters

Special details top

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
N	0.15859 (13)	0.23370 (12)	0.54691 (10)	0.0404 (3)
O1	0.42889 (14)	0.18278 (12)	0.57669 (13)	0.0633 (4)
O2	0.32304 (15)	−0.01044 (13)	0.44034 (11)	0.0627 (4)
C6	0.29872 (16)	0.39939 (15)	0.58608 (13)	0.0436 (3)
C8	0.09657 (17)	0.19375 (17)	0.45693 (14)	0.0487 (4)
H8A	0.0189	0.2606	0.4417	0.058*
H8B	0.0520	0.1132	0.4875	0.058*
C9	0.21273 (17)	0.17318 (17)	0.34271 (14)	0.0479 (4)
C19	0.06585 (15)	0.21269 (15)	0.67028 (13)	0.0432 (3)
H19A	0.1157	0.2486	0.7196	0.052*
C5	0.2872 (2)	0.52251 (17)	0.62205 (16)	0.0560 (4)
H5A	0.2120	0.5852	0.6064	0.067*
C1	0.41114 (16)	0.30665 (16)	0.61073 (14)	0.0468 (4)
C2	0.50701 (18)	0.3377 (2)	0.67020 (17)	0.0594 (5)
H2A	0.5813	0.2750	0.6872	0.071*
C14	0.32556 (18)	0.06974 (17)	0.33839 (15)	0.0509 (4)
C10	0.2111 (2)	0.2556 (2)	0.23952 (16)	0.0619 (5)
H10A	0.1357	0.3246	0.2419	0.074*
C13	0.4330 (2)	0.0513 (2)	0.23316 (17)	0.0639 (5)
H13A	0.5090	−0.0171	0.2303	0.077*
C4	0.3830 (2)	0.55644 (19)	0.68038 (17)	0.0634 (5)
C3	0.4923 (2)	0.4615 (2)	0.70427 (17)	0.0634 (5)
H3A	0.5574	0.4816	0.7442	0.076*
C12	0.4272 (2)	0.1345 (2)	0.13275 (18)	0.0745 (6)
H12A	0.4992	0.1200	0.0625	0.089*
C11	0.3180 (3)	0.2386 (2)	0.13297 (17)	0.0729 (6)
C20	0.0648 (3)	0.0674 (2)	0.71237 (18)	0.0735 (6)
H20A	0.1661	0.0253	0.6976	0.088*
H20B	0.0130	0.0273	0.6683	0.088*
C24	−0.0908 (2)	0.2822 (3)	0.69530 (19)	0.0811 (7)
H24A	−0.1468	0.2483	0.6505	0.097*
H24B	−0.0878	0.3750	0.6708	0.097*
C21	−0.0116 (3)	0.0471 (2)	0.8443 (2)	0.0883 (7)
H21A	−0.0157	−0.0457	0.8684	0.106*
H21B	0.0460	0.0794	0.8887	0.106*
C15	0.3654 (3)	0.6929 (2)	0.7176 (3)	0.0950 (8)
H15A	0.4601	0.7105	0.7263	0.114*
H15B	0.3409	0.7553	0.6550	0.114*
C23	−0.1674 (2)	0.2610 (3)	0.8282 (2)	0.0953 (9)
H23A	−0.1171	0.3032	0.8719	0.114*
H23B	−0.2694	0.3015	0.8428	0.114*
C17	0.3115 (4)	0.3322 (3)	0.0225 (2)	0.1067 (9)
H17A	0.2822	0.4205	0.0453	0.128*
H17B	0.4102	0.3302	−0.0312	0.128*
C22	−0.1661 (3)	0.1168 (3)	0.8725 (2)	0.0993 (9)
H22A	−0.2087	0.1074	0.9575	0.119*
H22B	−0.2272	0.0769	0.8362	0.119*
C16	0.2541 (4)	0.7143 (3)	0.8259 (3)	0.1463 (15)
H16A	0.2500	0.8027	0.8432	0.219*
H16B	0.2785	0.6548	0.8892	0.219*
H16C	0.1592	0.6998	0.8178	0.219*
C18	0.2088 (4)	0.3018 (5)	−0.0399 (3)	0.1597 (18)
H18A	0.2107	0.3637	−0.1083	0.240*
H18B	0.1100	0.3064	0.0118	0.240*
H18C	0.2379	0.2151	−0.0641	0.240*
C7	0.20041 (18)	0.36794 (15)	0.51474 (15)	0.0490 (4)
H7A	0.1110	0.4295	0.5272	0.059*
H7B	0.2520	0.3783	0.4313	0.059*
H1	0.347 (3)	0.176 (2)	0.548 (2)	0.107 (9)*
H2	0.398 (3)	−0.073 (3)	0.430 (2)	0.095 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N	0.0376 (6)	0.0464 (7)	0.0397 (6)	−0.0025 (5)	−0.0143 (5)	−0.0062 (5)
O1	0.0465 (6)	0.0623 (8)	0.0889 (10)	0.0105 (5)	−0.0289 (6)	−0.0287 (7)
O2	0.0614 (8)	0.0638 (8)	0.0573 (8)	0.0116 (6)	−0.0139 (6)	−0.0103 (6)
C6	0.0435 (8)	0.0465 (8)	0.0403 (8)	−0.0091 (6)	−0.0092 (6)	−0.0023 (6)
C8	0.0416 (8)	0.0629 (10)	0.0467 (8)	−0.0035 (7)	−0.0193 (6)	−0.0096 (7)
C9	0.0465 (8)	0.0600 (10)	0.0430 (8)	−0.0093 (7)	−0.0169 (7)	−0.0105 (7)
C19	0.0360 (7)	0.0535 (9)	0.0419 (8)	−0.0032 (6)	−0.0117 (6)	−0.0092 (6)
C5	0.0613 (10)	0.0481 (9)	0.0579 (10)	−0.0094 (8)	−0.0136 (8)	−0.0038 (8)
C1	0.0371 (7)	0.0554 (9)	0.0481 (9)	−0.0062 (6)	−0.0086 (6)	−0.0098 (7)
C2	0.0418 (8)	0.0740 (12)	0.0662 (11)	−0.0100 (8)	−0.0165 (8)	−0.0117 (9)
C14	0.0499 (9)	0.0589 (10)	0.0484 (9)	−0.0097 (7)	−0.0137 (7)	−0.0156 (7)
C10	0.0668 (11)	0.0746 (12)	0.0518 (10)	−0.0144 (9)	−0.0263 (9)	−0.0028 (9)
C13	0.0523 (10)	0.0784 (13)	0.0632 (12)	−0.0129 (9)	−0.0055 (8)	−0.0291 (10)
C4	0.0730 (12)	0.0642 (11)	0.0548 (10)	−0.0314 (10)	−0.0042 (9)	−0.0128 (8)
C3	0.0548 (10)	0.0844 (14)	0.0581 (11)	−0.0291 (10)	−0.0136 (8)	−0.0114 (9)
C12	0.0691 (12)	0.1093 (18)	0.0493 (11)	−0.0365 (12)	−0.0006 (9)	−0.0245 (11)
C11	0.0801 (14)	0.1002 (16)	0.0462 (10)	−0.0369 (12)	−0.0178 (9)	−0.0033 (10)
C20	0.0908 (15)	0.0628 (12)	0.0577 (11)	−0.0216 (10)	0.0021 (10)	−0.0050 (9)
C24	0.0465 (10)	0.128 (2)	0.0611 (12)	0.0191 (11)	−0.0117 (9)	−0.0200 (12)
C21	0.1108 (19)	0.0852 (16)	0.0598 (13)	−0.0401 (14)	0.0038 (12)	0.0003 (11)
C15	0.122 (2)	0.0749 (15)	0.0982 (18)	−0.0377 (14)	−0.0226 (16)	−0.0284 (13)
C23	0.0506 (11)	0.163 (3)	0.0645 (13)	0.0154 (14)	−0.0041 (9)	−0.0361 (16)
C17	0.130 (2)	0.145 (3)	0.0532 (13)	−0.0617 (19)	−0.0274 (14)	0.0172 (14)
C22	0.0791 (16)	0.167 (3)	0.0577 (13)	−0.0605 (17)	0.0003 (11)	−0.0198 (15)
C16	0.151 (3)	0.111 (2)	0.162 (3)	−0.030 (2)	0.020 (3)	−0.077 (2)
C18	0.156 (3)	0.253 (5)	0.091 (2)	−0.105 (3)	−0.064 (2)	0.063 (3)
C7	0.0528 (9)	0.0464 (9)	0.0505 (9)	−0.0030 (7)	−0.0218 (7)	−0.0001 (7)

Geometric parameters (Å, º) top

N—C7	1.474 (2)	C12—C11	1.380 (3)
N—C8	1.4756 (19)	C12—H12A	0.9300
N—C19	1.4833 (19)	C11—C17	1.527 (3)
O1—C1	1.373 (2)	C20—C21	1.525 (3)
O1—H1	0.94 (3)	C20—H20A	0.9700
O2—C14	1.364 (2)	C20—H20B	0.9700
O2—H2	0.88 (3)	C24—C23	1.536 (3)
C6—C5	1.381 (2)	C24—H24A	0.9700
C6—C1	1.390 (2)	C24—H24B	0.9700
C6—C7	1.506 (2)	C21—C22	1.498 (4)
C8—C9	1.503 (2)	C21—H21A	0.9700
C8—H8A	0.9700	C21—H21B	0.9700
C8—H8B	0.9700	C15—C16	1.433 (4)
C9—C10	1.393 (2)	C15—H15A	0.9700
C9—C14	1.393 (2)	C15—H15B	0.9700
C19—C24	1.515 (2)	C23—C22	1.516 (4)
C19—C20	1.522 (2)	C23—H23A	0.9700
C19—H19A	0.9800	C23—H23B	0.9700
C5—C4	1.384 (3)	C17—C18	1.458 (4)
C5—H5A	0.9300	C17—H17A	0.9700
C1—C2	1.382 (2)	C17—H17B	0.9700
C2—C3	1.375 (3)	C22—H22A	0.9700
C2—H2A	0.9300	C22—H22B	0.9700
C14—C13	1.386 (2)	C16—H16A	0.9600
C10—C11	1.393 (3)	C16—H16B	0.9600
C10—H10A	0.9300	C16—H16C	0.9600
C13—C12	1.377 (3)	C18—H18A	0.9600
C13—H13A	0.9300	C18—H18B	0.9600
C4—C3	1.379 (3)	C18—H18C	0.9600
C4—C15	1.514 (3)	C7—H7A	0.9700
C3—H3A	0.9300	C7—H7B	0.9700

C7—N—C8	111.05 (12)	C21—C20—H20B	109.5
C7—N—C19	112.92 (12)	H20A—C20—H20B	108.1
C8—N—C19	114.48 (11)	C19—C24—C23	109.84 (17)
C1—O1—H1	106.7 (16)	C19—C24—H24A	109.7
C14—O2—H2	111.5 (16)	C23—C24—H24A	109.7
C5—C6—C1	117.94 (15)	C19—C24—H24B	109.7
C5—C6—C7	121.62 (15)	C23—C24—H24B	109.7
C1—C6—C7	120.30 (14)	H24A—C24—H24B	108.2
N—C8—C9	112.25 (12)	C22—C21—C20	111.5 (2)
N—C8—H8A	109.2	C22—C21—H21A	109.3
C9—C8—H8A	109.2	C20—C21—H21A	109.3
N—C8—H8B	109.2	C22—C21—H21B	109.3
C9—C8—H8B	109.2	C20—C21—H21B	109.3
H8A—C8—H8B	107.9	H21A—C21—H21B	108.0
C10—C9—C14	118.44 (16)	C16—C15—C4	114.7 (2)
C10—C9—C8	121.57 (16)	C16—C15—H15A	108.6
C14—C9—C8	119.99 (15)	C4—C15—H15A	108.6
N—C19—C24	116.08 (14)	C16—C15—H15B	108.6
N—C19—C20	111.12 (13)	C4—C15—H15B	108.6
C24—C19—C20	110.84 (17)	H15A—C15—H15B	107.6
N—C19—H19A	106.0	C22—C23—C24	111.7 (2)
C24—C19—H19A	106.0	C22—C23—H23A	109.3
C20—C19—H19A	106.0	C24—C23—H23A	109.3
C6—C5—C4	122.68 (17)	C22—C23—H23B	109.3
C6—C5—H5A	118.7	C24—C23—H23B	109.3
C4—C5—H5A	118.7	H23A—C23—H23B	107.9
O1—C1—C2	118.84 (15)	C18—C17—C11	113.9 (2)
O1—C1—C6	120.72 (14)	C18—C17—H17A	108.8
C2—C1—C6	120.44 (16)	C11—C17—H17A	108.8
C3—C2—C1	119.93 (18)	C18—C17—H17B	108.8
C3—C2—H2A	120.0	C11—C17—H17B	108.8
C1—C2—H2A	120.0	H17A—C17—H17B	107.7
O2—C14—C13	122.99 (17)	C21—C22—C23	111.59 (18)
O2—C14—C9	117.11 (15)	C21—C22—H22A	109.3
C13—C14—C9	119.90 (17)	C23—C22—H22A	109.3
C11—C10—C9	122.5 (2)	C21—C22—H22B	109.3
C11—C10—H10A	118.8	C23—C22—H22B	109.3
C9—C10—H10A	118.8	H22A—C22—H22B	108.0
C12—C13—C14	119.99 (19)	C15—C16—H16A	109.5
C12—C13—H13A	120.0	C15—C16—H16B	109.5
C14—C13—H13A	120.0	H16A—C16—H16B	109.5
C3—C4—C5	117.73 (17)	C15—C16—H16C	109.5
C3—C4—C15	121.8 (2)	H16A—C16—H16C	109.5
C5—C4—C15	120.5 (2)	H16B—C16—H16C	109.5
C4—C3—C2	121.27 (17)	C17—C18—H18A	109.5
C4—C3—H3A	119.4	C17—C18—H18B	109.5
C2—C3—H3A	119.4	H18A—C18—H18B	109.5
C11—C12—C13	122.14 (18)	C17—C18—H18C	109.5
C11—C12—H12A	118.9	H18A—C18—H18C	109.5
C13—C12—H12A	118.9	H18B—C18—H18C	109.5
C12—C11—C10	117.07 (19)	N—C7—C6	112.32 (12)
C12—C11—C17	122.6 (2)	N—C7—H7A	109.1
C10—C11—C17	120.4 (2)	C6—C7—H7A	109.1
C19—C20—C21	110.63 (17)	N—C7—H7B	109.1
C19—C20—H20A	109.5	C6—C7—H7B	109.1
C21—C20—H20A	109.5	H7A—C7—H7B	107.9
C19—C20—H20B	109.5

C7—N—C8—C9	70.20 (17)	C6—C5—C4—C15	179.91 (18)
C19—N—C8—C9	−160.49 (13)	C5—C4—C3—C2	0.7 (3)
N—C8—C9—C10	−112.40 (16)	C15—C4—C3—C2	179.84 (19)
N—C8—C9—C14	67.57 (19)	C1—C2—C3—C4	0.1 (3)
C7—N—C19—C24	69.65 (18)	C14—C13—C12—C11	1.0 (3)
C8—N—C19—C24	−58.74 (19)	C13—C12—C11—C10	−1.0 (3)
C7—N—C19—C20	−162.49 (14)	C13—C12—C11—C17	179.35 (19)
C8—N—C19—C20	69.13 (18)	C9—C10—C11—C12	0.6 (3)
C1—C6—C5—C4	0.4 (2)	C9—C10—C11—C17	−179.71 (18)
C7—C6—C5—C4	−175.33 (16)	N—C19—C20—C21	171.75 (17)
C5—C6—C1—O1	−179.63 (15)	C24—C19—C20—C21	−57.6 (2)
C7—C6—C1—O1	−3.9 (2)	N—C19—C24—C23	−174.90 (18)
C5—C6—C1—C2	0.5 (2)	C20—C19—C24—C23	57.1 (2)
C7—C6—C1—C2	176.22 (15)	C19—C20—C21—C22	56.1 (3)
O1—C1—C2—C3	179.41 (16)	C3—C4—C15—C16	−97.6 (3)
C6—C1—C2—C3	−0.7 (3)	C5—C4—C15—C16	81.5 (3)
C10—C9—C14—O2	−179.05 (14)	C19—C24—C23—C22	−55.7 (3)
C8—C9—C14—O2	1.0 (2)	C12—C11—C17—C18	97.7 (3)
C10—C9—C14—C13	0.3 (2)	C10—C11—C17—C18	−81.9 (4)
C8—C9—C14—C13	−179.66 (14)	C20—C21—C22—C23	−54.7 (3)
C14—C9—C10—C11	−0.3 (3)	C24—C23—C22—C21	54.8 (3)
C8—C9—C10—C11	179.68 (16)	C8—N—C7—C6	−165.28 (12)
O2—C14—C13—C12	178.65 (16)	C19—N—C7—C6	64.58 (16)
C9—C14—C13—C12	−0.7 (3)	C5—C6—C7—N	−143.79 (15)
C6—C5—C4—C3	−1.0 (3)	C1—C6—C7—N	40.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.94 (3)	2.52 (2)	3.156 (2)	124.8 (18)
O1—H1···N	0.94 (3)	1.79 (3)	2.6352 (19)	147.8 (19)
O2—H2···O1ⁱ	0.88 (3)	1.84 (3)	2.708 (2)	168 (3)

Symmetry code: (i) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₄H₃₃NO₂
M_r	367.51
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	9.4224 (12), 10.3799 (16), 11.8143 (18)
α, β, γ (°)	82.140 (4), 73.960 (4), 81.676 (4)
V (Å³)	1093.1 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.90 × 0.44 × 0.24

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8721, 5350, 3648
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.665

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.185, 1.12
No. of reflections	5350
No. of parameters	252
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.23

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008 and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.94 (3)	2.52 (2)	3.156 (2)	124.8 (18)
O1—H1···N	0.94 (3)	1.79 (3)	2.6352 (19)	147.8 (19)
O2—H2···O1ⁱ	0.88 (3)	1.84 (3)	2.708 (2)	168 (3)

Symmetry code: (i) −x+1, −y, −z+1.

Acknowledgements

This work was supported by the Thailand Research Fund, Office of the Higher Education Commission, and Rajamangala University of Technology Thanyaburi (grant No. MRG5480046). The authors would like to thank the Department of Chemistry, Faculty of Science, Kasetsart University, and the Center of Advanced Studies in Industrial Technology, Faculty of Engineering, Kasetsart University for partial support.

References

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