4-[3-(Benzyl­amino)-2-hy­droxy­prop­yl]-2,6-di-tert-butyl­phenol

Asgarova, A.R.; Allahverdiyev, M.A.; Khalilov, A.N.; Gurbanov, A.V.; Brito, I.

doi:10.1107/S1600536811027115

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2024

doi:10.1107/S1600536811027115

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4-[3-(Benzylamino)-2-hydroxypropyl]-2,6-di-tert-butylphenol

Ayten R. Asgarova,^a Mirze A. Allahverdiyev,^a Ali. N. Khalilov,^a Atash V. Gurbanov ^a and Iván Brito ^b ^*

^aDepartment of Organic Chemistry, Baku State University, Baku, Azerbaijan, and ^bDepartamento de Química, Facultad de Ciencias Básicas, Universidad de Antofagasta, Casilla 170, Antofagasta, Chile
^*Correspondence e-mail: ivanbritob@yahoo.com

(Received 4 July 2011; accepted 6 July 2011; online 13 July 2011)

In the title compound, C₂₄H₃₅NO₂, the planes of the two aromatic rings form a dihedral angle of 72.76 (4)°. In the crystal, molecules are linked by O—H⋯O and O—H⋯N hydrogen-bond interactions, forming an extended two-dimensional framework parallel to the ab plane.

Related literature

For related compounds see: Asgarova et al. (2011 ); Krysin et al. (2010 $[Krysin, A. P., Tolstikova, T. G., Bryzgalov, A. O., Shul\'ts, E. E. & Shakirov, M. M. (2010). Russ. Patent RU 2396248 C1.]$ )

Experimental

Crystal data

C₂₄H₃₅NO₂
M_r = 369.53
Orthorhombic, P b c a
a = 9.8053 (10) Å
b = 18.870 (2) Å
c = 23.584 (3) Å
V = 4363.7 (8) Å³
Z = 8
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 296 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.979, T_max = 0.986
42619 measured reflections
4758 independent reflections
3478 reflections with I > 2σ(I)
R_int = 0.113

Refinement

R[F² > 2σ(F²)] = 0.091
wR(F²) = 0.243
S = 1.00
4758 reflections
250 parameters
H-atom parameters constrained
Δρ_max = 0.21 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	0.94	1.96	2.811 (3)	149
O2—H2O⋯N1ⁱⁱ	0.93	2.01	2.873 (4)	155
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT-Plus (Bruker, 2005); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: WinGX (Farrugia, 1997 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811027115/bt5572sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811027115/bt5572Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811027115/bt5572Isup3.cml

checkCIF report

Comment top

Fig. 1 shows the molecular structure of title compound, (I). The benzene ring is coplanar with four and two of C and H atoms of the tert-butyl groups respectively, and with the O atom of the hydroxyl group on the aliphatic chain [r.m.s 0.0068 Å] and make a dihedral angle of 72.76 (4)° with the phenyl ring. In the crystal structure the molecules are linked by O—H···O and O—H···N hydrogen bond interactions forming an extended two-dimensional framework parallel to the ab plane, Fig. 2. In the literature, pharmaceutical activity of other similar compounds such as di-3-(3,5-di-tert-butyl-4-hydroxyphnyl)-2-hydroxy-1-(N-isopopylamino)propanesuccinate (Krysin et al., 2010) has been reported.

Related literature top

For related compounds see: Asgarova et al. (2011); Krysin et al. (2010)

Experimental top

A mixture of 2,6-di-tert-butyl-4-(3-chloro-2-hydroxypropyl)phenol (0.2 g, 0.00067 mol), with benzylamine (0.2 g, 0.0019 mol) and 0.1 g NaOH (0.1 g, 0.025 mol) was stirred in water (10 ml) for 8 h at 373K. After cooling down, the organic layer which was unsoluble in water easily separated. Then this solid crude product was crystallized in isopropanole. After recrystallizing in DMSO single crystals were obtained. Yield 0.2g (80.97%). MP 135 °C. ¹H NMR (300 MHz, DMSO-d₆) δ 1.35 (s, 18H, 2(CH₃)₃), 1.98 (s, 1H, NH), 2.49 (d, 2H, CH₂Ar),3.43 (s, 1H, OH), 3.67 (s, 4H, 2CH₂N), 4.62 (s, 1H, OH), 6.91 (s, 2H, 2CH_arom), 7.27(s, 5H, 5CH_arom). ¹³CNMR (75 MHz, DMSO-d₆) δ 30.90, 34.83,42.11, 53.63, 54.92, 71.36, 125.79, 126.92, 128.40, 128.52, 130.75, 139.21,141.34, 152.29

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2005); data reduction: SAINT-Plus (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 1997).

Figures top

	Fig. 1. The structure of (I), showing the atom-numbering scheme. H atom were omitted for clarity. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A view of (I) showing the two-dimensional framework constructed via O—H··· O and O—H··· N hydrogen bonds. Hydrogen bonds are depicted as dashed lines [symmetry code: (i) -x + 1/2, y - 1/2, z; (ii) -x + 1,-y + 1,-z + 1]. The tert-butyl groups and all H atoms not involved in hydrogen bonds were omitted for clarity

4-[3-(Benzylamino)-2-hydroxypropyl]-2,6-di-tert-butylphenol top

Crystal data top

C₂₄H₃₅NO₂	F(000) = 1616
M_r = 369.53	D_x = 1.125 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 7811 reflections
a = 9.8053 (10) Å	θ = 2.3–26.2°
b = 18.870 (2) Å	µ = 0.07 mm⁻¹
c = 23.584 (3) Å	T = 296 K
V = 4363.7 (8) Å³	Prism, colourless
Z = 8	0.30 × 0.20 × 0.20 mm

Data collection top

Bruker APEXII CCD diffractometer	4758 independent reflections
Radiation source: fine-focus sealed tube	3478 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.113
ϕ and ω scans	θ_max = 27.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −12→12
T_min = 0.979, T_max = 0.986	k = −24→24
42619 measured reflections	l = −30→30

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)] = 0.091	Hydrogen site location: difference Fourier map
wR(F²) = 0.243	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.080P)² + 7.4283P] where P = (F_o² + 2F_c²)/3
4758 reflections	(Δ/σ)_max < 0.001
250 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₄H₃₅NO₂	V = 4363.7 (8) Å³
M_r = 369.53	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 9.8053 (10) Å	µ = 0.07 mm⁻¹
b = 18.870 (2) Å	T = 296 K
c = 23.584 (3) Å	0.30 × 0.20 × 0.20 mm

Data collection top

Bruker APEXII CCD diffractometer	4758 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	3478 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.986	R_int = 0.113
42619 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.091	0 restraints
wR(F²) = 0.243	H-atom parameters constrained
S = 1.00	Δρ_max = 0.21 e Å⁻³
4758 reflections	Δρ_min = −0.23 e Å⁻³
250 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
O1	0.0783 (2)	0.17031 (12)	0.38558 (11)	0.0539 (6)
H1O	0.1199	0.1281	0.3981	0.081*
O2	0.3869 (2)	0.54317 (11)	0.44598 (10)	0.0494 (6)
H2O	0.4808	0.5481	0.4444	0.074*
N1	0.3259 (3)	0.48697 (14)	0.55264 (11)	0.0423 (6)
H1N	0.3293	0.5355	0.5496	0.051*
C1	0.3085 (4)	0.50627 (18)	0.65547 (14)	0.0480 (8)
C2	0.4181 (4)	0.4740 (2)	0.68157 (17)	0.0638 (10)
H2A	0.4528	0.4319	0.6670	0.077*
C3	0.4768 (5)	0.5039 (3)	0.72923 (18)	0.0777 (13)
H3A	0.5519	0.4824	0.7461	0.093*
C4	0.4248 (5)	0.5646 (3)	0.75143 (18)	0.0820 (14)
H4A	0.4623	0.5837	0.7843	0.098*
C5	0.3186 (6)	0.5974 (3)	0.7259 (2)	0.0935 (16)
H5A	0.2850	0.6397	0.7406	0.112*
C6	0.2600 (5)	0.5680 (3)	0.67820 (18)	0.0720 (12)
H6A	0.1864	0.5906	0.6612	0.086*
C7	0.2441 (4)	0.4746 (2)	0.60383 (15)	0.0557 (9)
H7A	0.2332	0.4240	0.6094	0.067*
H7B	0.1541	0.4949	0.5986	0.067*
C8	0.2504 (3)	0.46587 (18)	0.50201 (13)	0.0447 (7)
H8A	0.1696	0.4952	0.4985	0.054*
H8B	0.2210	0.4170	0.5061	0.054*
C9	0.3352 (3)	0.47289 (16)	0.44903 (13)	0.0407 (7)
H9A	0.4125	0.4401	0.4518	0.049*
C10	0.2549 (4)	0.45515 (19)	0.39529 (14)	0.0508 (8)
H10A	0.1756	0.4857	0.3934	0.061*
H10B	0.3115	0.4655	0.3626	0.061*
C11	0.2085 (3)	0.37951 (17)	0.39179 (12)	0.0394 (7)
C12	0.2873 (3)	0.32842 (18)	0.36563 (13)	0.0438 (7)
H12A	0.3699	0.3420	0.3496	0.053*
C13	0.2495 (3)	0.25828 (18)	0.36215 (13)	0.0424 (7)
C14	0.1253 (3)	0.23858 (16)	0.38807 (12)	0.0373 (6)
C15	0.0408 (3)	0.28881 (15)	0.41439 (12)	0.0346 (6)
C16	0.0847 (3)	0.35827 (16)	0.41475 (12)	0.0380 (7)
H16A	0.0289	0.3924	0.4311	0.046*
C17	−0.0959 (3)	0.26783 (17)	0.44140 (14)	0.0447 (7)
C18	−0.0733 (4)	0.2144 (2)	0.48945 (18)	0.0654 (11)
H18A	−0.1587	0.2044	0.5077	0.098*
H18B	−0.0106	0.2338	0.5166	0.098*
H18C	−0.0363	0.1713	0.4741	0.098*
C19	−0.1680 (4)	0.3316 (2)	0.46782 (19)	0.0654 (11)
H19A	−0.2506	0.3162	0.4859	0.098*
H19B	−0.1893	0.3654	0.4388	0.098*
H19C	−0.1093	0.3531	0.4955	0.098*
C20	−0.1917 (4)	0.2370 (2)	0.3965 (2)	0.0698 (12)
H20A	−0.2779	0.2257	0.4137	0.105*
H20B	−0.1521	0.1947	0.3809	0.105*
H20C	−0.2052	0.2711	0.3669	0.105*
C21	0.3381 (4)	0.2040 (2)	0.33008 (16)	0.0582 (10)
C22	0.2571 (5)	0.1687 (3)	0.2829 (2)	0.105 (2)
H22A	0.3158	0.1376	0.2618	0.157*
H22B	0.2208	0.2043	0.2581	0.157*
H22C	0.1836	0.1418	0.2991	0.157*
C23	0.4598 (5)	0.2401 (3)	0.3017 (3)	0.106 (2)
H23A	0.5140	0.2052	0.2825	0.158*
H23B	0.5141	0.2634	0.3300	0.158*
H23C	0.4276	0.2744	0.2748	0.158*
C24	0.3973 (5)	0.1493 (3)	0.3702 (2)	0.0795 (13)
H24A	0.4552	0.1175	0.3494	0.119*
H24B	0.3245	0.1229	0.3875	0.119*
H24C	0.4496	0.1726	0.3990	0.119*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0534 (13)	0.0337 (12)	0.0747 (16)	0.0011 (10)	−0.0039 (12)	0.0016 (11)
O2	0.0490 (12)	0.0341 (12)	0.0651 (15)	−0.0086 (10)	0.0005 (11)	0.0037 (10)
N1	0.0461 (14)	0.0367 (14)	0.0442 (14)	−0.0042 (11)	0.0033 (11)	−0.0043 (11)
C1	0.0559 (19)	0.0449 (19)	0.0433 (17)	−0.0066 (15)	0.0131 (15)	0.0010 (15)
C2	0.082 (3)	0.054 (2)	0.056 (2)	0.004 (2)	0.005 (2)	−0.0031 (18)
C3	0.081 (3)	0.097 (4)	0.055 (2)	−0.005 (3)	−0.004 (2)	0.002 (2)
C4	0.089 (3)	0.114 (4)	0.044 (2)	−0.020 (3)	0.008 (2)	−0.017 (3)
C5	0.106 (4)	0.101 (4)	0.074 (3)	0.008 (3)	0.017 (3)	−0.035 (3)
C6	0.075 (3)	0.079 (3)	0.063 (2)	0.009 (2)	0.011 (2)	−0.016 (2)
C7	0.0503 (18)	0.060 (2)	0.057 (2)	−0.0098 (17)	0.0099 (17)	0.0030 (18)
C8	0.0410 (15)	0.0418 (17)	0.0514 (18)	−0.0083 (14)	−0.0009 (14)	−0.0021 (15)
C9	0.0427 (16)	0.0295 (15)	0.0500 (17)	−0.0063 (12)	−0.0011 (13)	0.0042 (13)
C10	0.0574 (19)	0.049 (2)	0.0456 (18)	−0.0123 (16)	−0.0049 (16)	0.0118 (15)
C11	0.0428 (16)	0.0410 (17)	0.0344 (14)	−0.0074 (13)	−0.0057 (12)	0.0083 (13)
C12	0.0372 (15)	0.057 (2)	0.0375 (15)	−0.0035 (14)	0.0003 (12)	0.0092 (15)
C13	0.0374 (14)	0.0522 (19)	0.0377 (15)	0.0077 (14)	0.0001 (13)	0.0034 (14)
C14	0.0381 (14)	0.0344 (16)	0.0395 (15)	0.0004 (12)	−0.0042 (12)	0.0053 (12)
C15	0.0354 (14)	0.0348 (15)	0.0335 (14)	0.0006 (12)	−0.0003 (11)	0.0029 (12)
C16	0.0418 (15)	0.0363 (16)	0.0359 (14)	0.0020 (13)	−0.0020 (12)	−0.0006 (12)
C17	0.0361 (15)	0.0415 (18)	0.0563 (19)	−0.0004 (13)	0.0069 (14)	0.0008 (15)
C18	0.064 (2)	0.063 (3)	0.069 (2)	0.0023 (19)	0.021 (2)	0.012 (2)
C19	0.051 (2)	0.067 (3)	0.078 (3)	0.0075 (19)	0.0229 (19)	0.002 (2)
C20	0.0408 (18)	0.068 (3)	0.101 (3)	−0.0070 (18)	−0.009 (2)	−0.005 (2)
C21	0.0445 (18)	0.073 (3)	0.057 (2)	0.0152 (18)	0.0074 (16)	−0.0003 (19)
C22	0.083 (3)	0.157 (6)	0.075 (3)	0.041 (4)	−0.010 (3)	−0.052 (3)
C23	0.074 (3)	0.128 (5)	0.115 (4)	0.025 (3)	0.051 (3)	0.007 (4)
C24	0.062 (2)	0.084 (3)	0.093 (3)	0.031 (2)	−0.002 (2)	−0.001 (3)

Geometric parameters (Å, º) top

O1—C14	1.370 (4)	C12—H12A	0.9300
O1—H1O	0.9421	C13—C14	1.412 (4)
O2—C9	1.422 (4)	C13—C21	1.541 (5)
O2—H2O	0.9261	C14—C15	1.404 (4)
N1—C8	1.460 (4)	C15—C16	1.380 (4)
N1—C7	1.468 (4)	C15—C17	1.536 (4)
N1—H1N	0.9181	C16—H16A	0.9300
C1—C6	1.368 (5)	C17—C19	1.528 (5)
C1—C2	1.381 (5)	C17—C20	1.530 (5)
C1—C7	1.496 (5)	C17—C18	1.533 (5)
C2—C3	1.383 (6)	C18—H18A	0.9600
C2—H2A	0.9300	C18—H18B	0.9600
C3—C4	1.359 (7)	C18—H18C	0.9600
C3—H3A	0.9300	C19—H19A	0.9600
C4—C5	1.352 (7)	C19—H19B	0.9600
C4—H4A	0.9300	C19—H19C	0.9600
C5—C6	1.380 (6)	C20—H20A	0.9600
C5—H5A	0.9300	C20—H20B	0.9600
C6—H6A	0.9300	C20—H20C	0.9600
C7—H7A	0.9700	C21—C24	1.516 (6)
C7—H7B	0.9700	C21—C22	1.521 (6)
C8—C9	1.507 (4)	C21—C23	1.528 (6)
C8—H8A	0.9700	C22—H22A	0.9600
C8—H8B	0.9700	C22—H22B	0.9600
C9—C10	1.529 (4)	C22—H22C	0.9600
C9—H9A	0.9800	C23—H23A	0.9600
C10—C11	1.500 (5)	C23—H23B	0.9600
C10—H10A	0.9700	C23—H23C	0.9600
C10—H10B	0.9700	C24—H24A	0.9600
C11—C12	1.381 (5)	C24—H24B	0.9600
C11—C16	1.388 (4)	C24—H24C	0.9600
C12—C13	1.377 (5)

C14—O1—H1O	129.5	O1—C14—C13	121.3 (3)
C9—O2—H2O	116.8	C15—C14—C13	121.5 (3)
C8—N1—C7	110.6 (2)	C16—C15—C14	117.4 (3)
C8—N1—H1N	103.2	C16—C15—C17	121.0 (3)
C7—N1—H1N	104.0	C14—C15—C17	121.7 (3)
C6—C1—C2	118.1 (4)	C15—C16—C11	123.0 (3)
C6—C1—C7	120.9 (4)	C15—C16—H16A	118.5
C2—C1—C7	121.0 (3)	C11—C16—H16A	118.5
C1—C2—C3	120.4 (4)	C19—C17—C20	107.3 (3)
C1—C2—H2A	119.8	C19—C17—C18	106.5 (3)
C3—C2—H2A	119.8	C20—C17—C18	110.4 (3)
C4—C3—C2	120.1 (5)	C19—C17—C15	111.7 (3)
C4—C3—H3A	120.0	C20—C17—C15	110.3 (3)
C2—C3—H3A	120.0	C18—C17—C15	110.5 (3)
C5—C4—C3	120.2 (4)	C17—C18—H18A	109.5
C5—C4—H4A	119.9	C17—C18—H18B	109.5
C3—C4—H4A	119.9	H18A—C18—H18B	109.5
C4—C5—C6	119.9 (5)	C17—C18—H18C	109.5
C4—C5—H5A	120.0	H18A—C18—H18C	109.5
C6—C5—H5A	120.0	H18B—C18—H18C	109.5
C1—C6—C5	121.2 (5)	C17—C19—H19A	109.5
C1—C6—H6A	119.4	C17—C19—H19B	109.5
C5—C6—H6A	119.4	H19A—C19—H19B	109.5
N1—C7—C1	112.0 (3)	C17—C19—H19C	109.5
N1—C7—H7A	109.2	H19A—C19—H19C	109.5
C1—C7—H7A	109.2	H19B—C19—H19C	109.5
N1—C7—H7B	109.2	C17—C20—H20A	109.5
C1—C7—H7B	109.2	C17—C20—H20B	109.5
H7A—C7—H7B	107.9	H20A—C20—H20B	109.5
N1—C8—C9	112.0 (2)	C17—C20—H20C	109.5
N1—C8—H8A	109.2	H20A—C20—H20C	109.5
C9—C8—H8A	109.2	H20B—C20—H20C	109.5
N1—C8—H8B	109.2	C24—C21—C22	110.9 (4)
C9—C8—H8B	109.2	C24—C21—C23	106.1 (4)
H8A—C8—H8B	107.9	C22—C21—C23	106.4 (4)
O2—C9—C8	108.7 (3)	C24—C21—C13	111.3 (3)
O2—C9—C10	110.2 (3)	C22—C21—C13	110.8 (3)
C8—C9—C10	112.6 (3)	C23—C21—C13	111.1 (4)
O2—C9—H9A	108.4	C21—C22—H22A	109.5
C8—C9—H9A	108.4	C21—C22—H22B	109.5
C10—C9—H9A	108.4	H22A—C22—H22B	109.5
C11—C10—C9	114.2 (3)	C21—C22—H22C	109.5
C11—C10—H10A	108.7	H22A—C22—H22C	109.5
C9—C10—H10A	108.7	H22B—C22—H22C	109.5
C11—C10—H10B	108.7	C21—C23—H23A	109.5
C9—C10—H10B	108.7	C21—C23—H23B	109.5
H10A—C10—H10B	107.6	H23A—C23—H23B	109.5
C12—C11—C16	117.5 (3)	C21—C23—H23C	109.5
C12—C11—C10	121.3 (3)	H23A—C23—H23C	109.5
C16—C11—C10	121.2 (3)	H23B—C23—H23C	109.5
C13—C12—C11	123.2 (3)	C21—C24—H24A	109.5
C13—C12—H12A	118.4	C21—C24—H24B	109.5
C11—C12—H12A	118.4	H24A—C24—H24B	109.5
C12—C13—C14	117.4 (3)	C21—C24—H24C	109.5
C12—C13—C21	121.1 (3)	H24A—C24—H24C	109.5
C14—C13—C21	121.6 (3)	H24B—C24—H24C	109.5
O1—C14—C15	117.1 (3)

C6—C1—C2—C3	−0.2 (6)	C21—C13—C14—O1	−0.2 (4)
C7—C1—C2—C3	179.9 (4)	C12—C13—C14—C15	2.5 (4)
C1—C2—C3—C4	1.4 (7)	C21—C13—C14—C15	−176.2 (3)
C2—C3—C4—C5	−2.3 (7)	O1—C14—C15—C16	−177.1 (3)
C3—C4—C5—C6	2.0 (8)	C13—C14—C15—C16	−1.0 (4)
C2—C1—C6—C5	−0.2 (6)	O1—C14—C15—C17	2.4 (4)
C7—C1—C6—C5	179.8 (4)	C13—C14—C15—C17	178.5 (3)
C4—C5—C6—C1	−0.7 (8)	C14—C15—C16—C11	−1.7 (4)
C8—N1—C7—C1	−170.7 (3)	C17—C15—C16—C11	178.8 (3)
C6—C1—C7—N1	103.3 (4)	C12—C11—C16—C15	2.6 (4)
C2—C1—C7—N1	−76.8 (4)	C10—C11—C16—C15	−177.4 (3)
C7—N1—C8—C9	−175.8 (3)	C16—C15—C17—C19	−1.2 (4)
N1—C8—C9—O2	−54.2 (3)	C14—C15—C17—C19	179.3 (3)
N1—C8—C9—C10	−176.6 (3)	C16—C15—C17—C20	118.1 (3)
O2—C9—C10—C11	173.9 (3)	C14—C15—C17—C20	−61.4 (4)
C8—C9—C10—C11	−64.5 (4)	C16—C15—C17—C18	−119.5 (3)
C9—C10—C11—C12	−91.6 (4)	C14—C15—C17—C18	61.0 (4)
C9—C10—C11—C16	88.4 (4)	C12—C13—C21—C24	114.3 (4)
C16—C11—C12—C13	−0.9 (4)	C14—C13—C21—C24	−67.0 (4)
C10—C11—C12—C13	179.1 (3)	C12—C13—C21—C22	−121.8 (4)
C11—C12—C13—C14	−1.6 (5)	C14—C13—C21—C22	56.9 (5)
C11—C12—C13—C21	177.2 (3)	C12—C13—C21—C23	−3.8 (5)
C12—C13—C14—O1	178.5 (3)	C14—C13—C21—C23	174.9 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O2ⁱ	0.94	1.96	2.811 (3)	149
O2—H2O···N1ⁱⁱ	0.93	2.01	2.873 (4)	155

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

Experimental details

Crystal data
Chemical formula	C₂₄H₃₅NO₂
M_r	369.53
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	9.8053 (10), 18.870 (2), 23.584 (3)
V (Å³)	4363.7 (8)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.979, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	42619, 4758, 3478
R_int	0.113
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.091, 0.243, 1.00
No. of reflections	4758
No. of parameters	250
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.23

Computer programs: APEX2 (Bruker, 2005), SAINT-Plus (Bruker, 2005), SHELXTL (Sheldrick, 2008), WinGX (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O2ⁱ	0.94	1.96	2.811 (3)	149
O2—H2O···N1ⁱⁱ	0.93	2.01	2.873 (4)	155

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

Acknowledgements

The authors are grateful to Baku State University for supporting this study. IB thanks the Spanish Research Council (CSIC) for the provision of a free-of-charge licence to the Cambridge Structural Database.

References

Asgarova, A. R., Maharramov, A. M., Khalilov, A. N., Gurbanov, A. V. & Ng, S. W. (2011). Acta Cryst. E67, o852. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2005). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Krysin, A. P., Tolstikova, T. G., Bryzgalov, A. O., Shul\'ts, E. E. & Shakirov, M. M. (2010). Russ. Patent RU 2396248 C1. Google Scholar
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar