4,4′,6,6′-Tetra-tert-butyl-2,2′-[1,2-phenyl­enebis(nitrilo­methyl­idyne)]diphenol acetone solvate

Eltayeb, N.E.; Teoh, S.G.; Chantrapromma, S.; Fun, H.-K.; Adnan, R.

doi:10.1107/S1600536808003905

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 3| March 2008| Pages o576-o577

doi:10.1107/S1600536808003905

Open

access

4,4′,6,6′-Tetra-tert-butyl-2,2′-[1,2-phenylenebis(nitrilomethylidyne)]diphenol acetone solvate

Naser Eltaher Eltayeb,^a ‡ Siang Guan Teoh,^a Suchada Chantrapromma,^b § Hoong-Kun Fun ^c ^* and Rohana Adnan ^a

^aSchool of Chemical Science, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 23 January 2008; accepted 6 February 2008; online 13 February 2008)

In the Schiff base molecule of the title compound, C₃₆H₄₈N₂O₂·C₃H₆O, the central benzene ring makes dihedral angles of 46.64 (10) and 49.34 (10)° with the two outer benzene rings, and the two outer benzene rings form an angle of 39.13 (8)°. There are two intramolecular O—H⋯N hydrogen bonds involving the two hydroxy groups, which generate S(6) ring motifs. In the crystal structure, the Schiff base molecules are linked into a chain along the a axis by C—H⋯π interactions. The acetone solvent molecules are attached to the chain via C—H⋯O hydrogen bonds.

Related literature

For bond-length data, see: Allen et al. (1987 ). For ring-motifs, see: Bernstein et al. (1995 ). For biological activities of Schiff base compounds, see: Dao et al. (2000 ); Eltayeb & Ahmed (2005a ,b ); Karthikeyan et al. (2006 ); Sriram et al. (2006 ). For related structures, see: Eltayeb, Teoh, Chantrapromma et al. (2007 ); Eltayeb, Teoh, Teh et al. (2007a ,b ).

Experimental

Crystal data

C₃₆H₄₈N₂O₂·C₃H₆O
M_r = 598.84
Triclinic, $[P \overline 1]$
a = 10.0008 (2) Å
b = 12.0020 (3) Å
c = 17.0366 (4) Å
α = 82.068 (1)°
β = 86.320 (1)°
γ = 65.764 (1)°
V = 1846.76 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 296 (2) K
0.59 × 0.55 × 0.43 mm

Data collection

Bruker SMART APEX2 CCD area-detecto diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.962, T_max = 0.972
26090 measured reflections
8384 independent reflections
5874 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.183
S = 1.04
8384 reflections
419 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the C1–C6 and C15–C20 ring centroids, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯N1	0.89 (2)	1.76 (3)	2.5809 (19)	153 (3)
O2—H1O2⋯N2	0.87 (3)	1.78 (3)	2.5956 (19)	155 (3)
C7—H7A⋯O3	0.93	2.58	3.460 (6)	158
C30—H30B⋯O2	0.96	2.36	2.994 (3)	123
C31—H31A⋯O2	0.96	2.34	2.989 (3)	124
C34—H34C⋯O1	0.96	2.32	2.968 (3)	124
C35—H35A⋯O1	0.96	2.35	2.996 (3)	124
C24—H24B⋯Cg2ⁱ	0.96	2.97	3.877 (3)	158
C26—H26A⋯Cg1ⁱⁱ	0.96	2.89	3.798 (2)	157
Symmetry codes: (i) x+1, y, z; (ii) x-1, y, z.

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); 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: SHELXTL and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808003905/ci2559sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808003905/ci2559Isup2.hkl

checkCIF report

Comment top

Schiff base compounds have received much attention because of their potential applications. Some of these compounds exhibit various pharmacological activities, such as anticancer (Dao et al., 2000), anti-HIV (Sriram et al., 2006), antibacterial and antifungal (Karthikeyan et al., 2006) properties. In addition, some of them may be used as analytical reagents for the determination of trace elements (Eltayeb & Ahmed, 2005a,b). Recently, we have reported the crystal structures of 2,2'-[1,2-phenylenebis(nitrilomethylidyne)]bis(5-methylphenol) (Eltayeb et al., 2007a) and 6,6'-dimethyl-2,2'-[1,2-phenylenebis(nitrilomethylidyne)]diphenol (Eltayeb et al., 2007b). In this paper, we report the crystal structure of the title compound, obtained by the reaction of o-phenylenediamine and 3,5-di-tert-butylsalicylaldehyde.

In the molecular structure of the title compound, the central benzene ring (C8–13) makes dihedral angles of 46.64 (10)° and 49.34 (10)°, respectively, with the two outer benzene rings, C1—C6 and C15—C20. The dihedral angle between the two outer benzene rings is 39.13 (8)°. The C8–N1–C7–C6 and C13–N2–C14–C15 torsion angles are 178.16 (15)° and -178.34 (16)°, respectively. Bond lengths and angles in the title compound are in normal ranges (Allen et al., 1987) and are comparable to those in related structures (Eltayeb et al., 2007; Eltayeb et al., 2007a,b).

The two intramolecular O—H···O hydrogen bonds, O1—H1O1···N1 and O2—H1O2···N2, generate S(6) ring motifs (Bernstein et al., 1995). In addition, intramolecular C—H···O interactions (Table 1) are observed.

In the crystal structure, the acetone molecule is linked to the Schiff base molecule via a C—H···O hydrogen bond. The crystal structure is further stabilized by C—H···π interactions involving the C1–C6 (centroid Cg1) and C15–C20 (centroid Cg2) rings, which link the molecules into a chain along the a axis.

Related literature top

For bond-length data, see: Allen et al. (1987). For ring-motifs, see: Bernstein et al. (1995). For biological activities of Schiff base compounds, see: Dao et al. (2000); Eltayeb & Ahmed (2005a,b); Karthikeyan et al. (2006); Sriram et al. (2006). For related structures, see: Eltayeb, Teoh, Chantrapromma et al. (2007); Eltayeb, Teoh, Teh et al. (2007a,b).

Experimental top

The title compound was synthesized by adding 3,5-di-tert-butylsalicylaldehyde (0.936 g, 4 mmol) to a solution of o-phenylenediamine (0.216 g, 2 mmol) in ethanol 95% (20 ml). The mixture was refluxed with stirring for 30 min. The resultant yellow solution was filtered. The yellow precipitate obtained after a few days, was dissolved in acetone (20 ml). Orange single crystals suitable for X-ray diffraction were formed after 6 d of slow evaporation of the acetone at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (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: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The asymmetric unit of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering. Hydrogen bonds are shown as dashed lines.
	Fig. 2. Part of the crystal packing of the title compound, showing a C—H···π bonded (dashed lines) chain along the a axis. For clarity, the solvent molecules and H atoms not involved in the interactions have been omitted.

4,4',6,6'-Tetra-tert-butyl-2,2'-[1,2- phenylenebis(nitrilomethylidyne)]diphenol acetone solvate top

Crystal data top

C₃₆H₄₈N₂O₂·C₃H₆O	Z = 2
M_r = 598.84	F(000) = 652
Triclinic, P1	D_x = 1.077 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.0008 (2) Å	Cell parameters from 8384 reflections
b = 12.0020 (3) Å	θ = 1.9–27.5°
c = 17.0366 (4) Å	µ = 0.07 mm⁻¹
α = 82.068 (1)°	T = 296 K
β = 86.320 (1)°	Block, orange
γ = 65.764 (1)°	0.59 × 0.55 × 0.43 mm
V = 1846.76 (7) Å³

Data collection top

Bruker SMART APEX2 CCD area-detecto diffractometer	8384 independent reflections
Radiation source: fine-focus sealed tube	5874 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
Detector resolution: 8.33 pixels mm^-1	θ_max = 27.5°, θ_min = 1.9°
ω scans	h = −11→12
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −15→15
T_min = 0.962, T_max = 0.972	l = −22→22
26090 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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.183	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.085P)² + 0.5109P] where P = (F_o² + 2F_c²)/3
8384 reflections	(Δ/σ)_max = 0.001
419 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₃₆H₄₈N₂O₂·C₃H₆O	γ = 65.764 (1)°
M_r = 598.84	V = 1846.76 (7) Å³
Triclinic, P1	Z = 2
a = 10.0008 (2) Å	Mo Kα radiation
b = 12.0020 (3) Å	µ = 0.07 mm⁻¹
c = 17.0366 (4) Å	T = 296 K
α = 82.068 (1)°	0.59 × 0.55 × 0.43 mm
β = 86.320 (1)°

Data collection top

Bruker SMART APEX2 CCD area-detecto diffractometer	8384 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	5874 reflections with I > 2σ(I)
T_min = 0.962, T_max = 0.972	R_int = 0.022
26090 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	0 restraints
wR(F²) = 0.183	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.45 e Å⁻³
8384 reflections	Δρ_min = −0.28 e Å⁻³
419 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	0.24853 (14)	0.02581 (13)	0.23910 (8)	0.0551 (3)
O2	−0.02994 (14)	0.37492 (14)	0.24879 (8)	0.0560 (4)
N1	0.25681 (16)	0.14200 (13)	0.10087 (8)	0.0460 (3)
N2	−0.01847 (16)	0.32660 (14)	0.10401 (8)	0.0459 (3)
C1	0.38900 (17)	0.00930 (15)	0.24923 (10)	0.0407 (4)
C2	0.45915 (18)	−0.04982 (14)	0.32187 (10)	0.0413 (4)
C3	0.60129 (18)	−0.06050 (15)	0.32878 (10)	0.0449 (4)
H3A	0.6489	−0.0987	0.3765	0.054*
C4	0.67862 (18)	−0.01843 (15)	0.26978 (11)	0.0451 (4)
C5	0.60684 (19)	0.03771 (16)	0.19953 (11)	0.0460 (4)
H5A	0.6550	0.0666	0.1586	0.055*
C6	0.46270 (18)	0.05235 (15)	0.18822 (10)	0.0421 (4)
C7	0.3908 (2)	0.11843 (16)	0.11444 (10)	0.0449 (4)
H7A	0.4441	0.1448	0.0753	0.054*
C8	0.19331 (19)	0.21018 (16)	0.02816 (9)	0.0447 (4)
C9	0.2644 (2)	0.1850 (2)	−0.04413 (11)	0.0614 (5)
H9A	0.3569	0.1211	−0.0455	0.074*
C10	0.1993 (3)	0.2537 (2)	−0.11419 (11)	0.0704 (6)
H10A	0.2480	0.2363	−0.1623	0.084*
C11	0.0627 (3)	0.3476 (2)	−0.11230 (11)	0.0668 (6)
H11A	0.0196	0.3952	−0.1592	0.080*
C12	−0.0113 (2)	0.37196 (19)	−0.04127 (11)	0.0575 (5)
H12A	−0.1044	0.4354	−0.0406	0.069*
C13	0.05201 (19)	0.30244 (16)	0.02944 (9)	0.0438 (4)
C14	−0.1540 (2)	0.34565 (17)	0.11173 (10)	0.0489 (4)
H14A	−0.2026	0.3410	0.0683	0.059*
C15	−0.23510 (19)	0.37409 (16)	0.18511 (10)	0.0449 (4)
C16	−0.38016 (19)	0.38473 (17)	0.18917 (11)	0.0489 (4)
H16A	−0.4213	0.3742	0.1448	0.059*
C17	−0.46321 (18)	0.41034 (15)	0.25708 (11)	0.0445 (4)
C18	−0.39582 (18)	0.42637 (15)	0.32176 (10)	0.0439 (4)
H18A	−0.4512	0.4449	0.3679	0.053*
C19	−0.25311 (18)	0.41677 (15)	0.32213 (10)	0.0417 (4)
C20	−0.17137 (18)	0.38860 (16)	0.25182 (10)	0.0424 (4)
C21	0.8335 (2)	−0.03120 (18)	0.28575 (13)	0.0549 (5)
C22	0.9056 (3)	0.0030 (4)	0.20973 (19)	0.1070 (11)
H22A	0.9107	−0.0499	0.1711	0.160*
H22B	1.0028	−0.0068	0.2212	0.160*
H22C	0.8485	0.0870	0.1892	0.160*
C23	0.9286 (3)	−0.1632 (3)	0.3171 (3)	0.1184 (13)
H23A	0.8956	−0.1825	0.3693	0.178*
H23B	1.0287	−0.1732	0.3194	0.178*
H23C	0.9218	−0.2174	0.2826	0.178*
C24	0.8236 (3)	0.0569 (3)	0.3431 (2)	0.0993 (10)
H24A	0.7817	0.0362	0.3923	0.149*
H24B	0.7628	0.1394	0.3212	0.149*
H24C	0.9199	0.0513	0.3524	0.149*
C25	−0.62039 (19)	0.41811 (17)	0.26502 (12)	0.0504 (4)
C26	−0.6241 (3)	0.3137 (2)	0.32638 (16)	0.0759 (7)
H26A	−0.5579	0.2361	0.3104	0.114*
H26B	−0.7218	0.3169	0.3304	0.114*
H26C	−0.5950	0.3226	0.3770	0.114*
C27	−0.6760 (2)	0.4069 (2)	0.18631 (15)	0.0714 (6)
H27A	−0.6773	0.4737	0.1477	0.107*
H27B	−0.7733	0.4100	0.1935	0.107*
H27C	−0.6122	0.3301	0.1683	0.107*
C28	−0.7245 (2)	0.5417 (2)	0.29181 (15)	0.0668 (6)
H28A	−0.7242	0.6076	0.2529	0.100*
H28B	−0.6925	0.5502	0.3417	0.100*
H28C	−0.8220	0.5447	0.2975	0.100*
C29	−0.1868 (2)	0.43580 (17)	0.39531 (10)	0.0487 (4)
C30	−0.1413 (3)	0.5437 (2)	0.37445 (14)	0.0736 (6)
H30A	−0.2253	0.6167	0.3564	0.110*
H30B	−0.0679	0.5251	0.3333	0.110*
H30C	−0.1022	0.5571	0.4206	0.110*
C31	−0.0546 (3)	0.3177 (2)	0.42414 (13)	0.0756 (7)
H31A	0.0179	0.2971	0.3827	0.113*
H31B	−0.0856	0.2516	0.4381	0.113*
H31C	−0.0133	0.3304	0.4697	0.113*
C32	−0.2966 (2)	0.4672 (2)	0.46406 (11)	0.0639 (5)
H32A	−0.3809	0.5410	0.4477	0.096*
H32B	−0.2516	0.4797	0.5082	0.096*
H32C	−0.3263	0.4007	0.4794	0.096*
C33	0.3806 (2)	−0.09823 (17)	0.38899 (10)	0.0485 (4)
C34	0.2432 (2)	0.0077 (2)	0.41472 (13)	0.0718 (6)
H34A	0.2702	0.0686	0.4316	0.108*
H34B	0.1960	−0.0233	0.4578	0.108*
H34C	0.1770	0.0441	0.3709	0.108*
C35	0.3409 (3)	−0.1970 (2)	0.36056 (14)	0.0717 (6)
H35A	0.2795	−0.1620	0.3148	0.108*
H35B	0.2896	−0.2264	0.4021	0.108*
H35C	0.4290	−0.2643	0.3470	0.108*
C36	0.4771 (2)	−0.15914 (19)	0.46241 (11)	0.0597 (5)
H36A	0.5021	−0.0995	0.4828	0.090*
H36B	0.5651	−0.2258	0.4481	0.090*
H36C	0.4245	−0.1902	0.5023	0.090*
O3	0.6258 (5)	0.2364 (5)	0.0147 (2)	0.227 (2)
C37	0.8191 (10)	0.1323 (9)	−0.0542 (7)	0.345 (8)
H37A	0.8795	0.1561	−0.0245	0.517*
H37B	0.8476	0.1354	−0.1090	0.517*
H37C	0.8309	0.0501	−0.0342	0.517*
C38	0.6661 (8)	0.2165 (6)	−0.0462 (2)	0.176 (3)
C39	0.5935 (11)	0.2473 (7)	−0.1217 (3)	0.266 (5)
H39A	0.5220	0.3310	−0.1262	0.399*
H39B	0.5456	0.1933	−0.1254	0.399*
H39C	0.6646	0.2381	−0.1637	0.399*
H1O1	0.221 (3)	0.072 (2)	0.1925 (15)	0.083 (8)*
H1O2	0.001 (3)	0.353 (2)	0.2023 (16)	0.084 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0384 (7)	0.0755 (9)	0.0528 (7)	−0.0286 (6)	−0.0115 (6)	0.0104 (6)
O2	0.0366 (7)	0.0876 (10)	0.0494 (7)	−0.0283 (7)	0.0041 (6)	−0.0191 (7)
N1	0.0396 (8)	0.0530 (8)	0.0396 (7)	−0.0134 (7)	−0.0015 (6)	−0.0038 (6)
N2	0.0390 (8)	0.0555 (8)	0.0398 (7)	−0.0151 (7)	0.0017 (6)	−0.0090 (6)
C1	0.0317 (8)	0.0428 (8)	0.0479 (9)	−0.0149 (7)	−0.0043 (7)	−0.0050 (7)
C2	0.0369 (9)	0.0401 (8)	0.0471 (9)	−0.0157 (7)	−0.0050 (7)	−0.0041 (7)
C3	0.0379 (9)	0.0432 (9)	0.0523 (9)	−0.0144 (7)	−0.0097 (8)	−0.0040 (7)
C4	0.0312 (8)	0.0437 (9)	0.0605 (10)	−0.0134 (7)	−0.0016 (8)	−0.0124 (7)
C5	0.0356 (9)	0.0499 (9)	0.0530 (10)	−0.0180 (8)	0.0053 (7)	−0.0088 (7)
C6	0.0359 (9)	0.0441 (8)	0.0444 (8)	−0.0136 (7)	−0.0004 (7)	−0.0073 (7)
C7	0.0420 (9)	0.0495 (9)	0.0412 (8)	−0.0169 (8)	0.0051 (7)	−0.0068 (7)
C8	0.0452 (10)	0.0494 (9)	0.0367 (8)	−0.0163 (8)	−0.0004 (7)	−0.0055 (7)
C9	0.0559 (12)	0.0681 (12)	0.0441 (10)	−0.0087 (10)	0.0054 (9)	−0.0112 (9)
C10	0.0746 (15)	0.0860 (15)	0.0364 (9)	−0.0185 (13)	0.0076 (9)	−0.0103 (9)
C11	0.0787 (15)	0.0719 (13)	0.0367 (9)	−0.0194 (12)	−0.0073 (9)	0.0030 (8)
C12	0.0537 (11)	0.0595 (11)	0.0466 (10)	−0.0104 (9)	−0.0061 (9)	−0.0029 (8)
C13	0.0446 (10)	0.0488 (9)	0.0372 (8)	−0.0175 (8)	−0.0008 (7)	−0.0074 (7)
C14	0.0427 (10)	0.0597 (10)	0.0431 (9)	−0.0176 (9)	−0.0041 (8)	−0.0109 (8)
C15	0.0356 (9)	0.0530 (9)	0.0445 (9)	−0.0155 (8)	0.0001 (7)	−0.0089 (7)
C16	0.0385 (9)	0.0598 (10)	0.0487 (9)	−0.0181 (8)	−0.0047 (8)	−0.0119 (8)
C17	0.0327 (9)	0.0433 (8)	0.0558 (10)	−0.0133 (7)	−0.0003 (7)	−0.0076 (7)
C18	0.0375 (9)	0.0458 (9)	0.0466 (9)	−0.0151 (7)	0.0046 (7)	−0.0079 (7)
C19	0.0392 (9)	0.0434 (8)	0.0429 (8)	−0.0171 (7)	0.0012 (7)	−0.0063 (7)
C20	0.0336 (8)	0.0486 (9)	0.0458 (9)	−0.0170 (7)	−0.0008 (7)	−0.0068 (7)
C21	0.0337 (9)	0.0586 (11)	0.0756 (13)	−0.0206 (8)	−0.0056 (9)	−0.0100 (9)
C22	0.0550 (15)	0.169 (3)	0.113 (2)	−0.0639 (19)	0.0065 (15)	−0.014 (2)
C23	0.0403 (13)	0.0770 (17)	0.225 (4)	−0.0162 (12)	−0.0399 (18)	0.016 (2)
C24	0.0628 (16)	0.123 (2)	0.133 (2)	−0.0449 (16)	−0.0094 (16)	−0.056 (2)
C25	0.0330 (9)	0.0524 (10)	0.0653 (11)	−0.0167 (8)	−0.0002 (8)	−0.0076 (8)
C26	0.0548 (13)	0.0703 (14)	0.1036 (18)	−0.0326 (11)	−0.0001 (12)	0.0087 (13)
C27	0.0423 (11)	0.0876 (16)	0.0907 (16)	−0.0283 (11)	−0.0076 (11)	−0.0222 (13)
C28	0.0402 (11)	0.0654 (12)	0.0904 (15)	−0.0158 (10)	0.0093 (10)	−0.0183 (11)
C29	0.0464 (10)	0.0596 (10)	0.0438 (9)	−0.0237 (9)	0.0002 (8)	−0.0122 (8)
C30	0.0842 (17)	0.0917 (16)	0.0721 (14)	−0.0584 (14)	0.0134 (12)	−0.0312 (12)
C31	0.0637 (14)	0.0875 (16)	0.0606 (12)	−0.0127 (12)	−0.0173 (11)	−0.0103 (11)
C32	0.0688 (14)	0.0813 (14)	0.0479 (10)	−0.0347 (12)	0.0078 (10)	−0.0191 (10)
C33	0.0442 (10)	0.0535 (10)	0.0484 (9)	−0.0227 (8)	−0.0074 (8)	0.0037 (7)
C34	0.0514 (12)	0.0857 (15)	0.0601 (12)	−0.0141 (11)	0.0040 (10)	0.0031 (11)
C35	0.0855 (16)	0.0786 (14)	0.0700 (13)	−0.0571 (13)	−0.0198 (12)	0.0145 (11)
C36	0.0620 (13)	0.0645 (12)	0.0500 (10)	−0.0255 (10)	−0.0116 (9)	0.0062 (9)
O3	0.243 (4)	0.409 (7)	0.144 (3)	−0.231 (5)	0.094 (3)	−0.137 (3)
C37	0.305 (11)	0.372 (13)	0.507 (18)	−0.242 (10)	0.246 (12)	−0.320 (13)
C38	0.300 (7)	0.273 (6)	0.091 (3)	−0.247 (6)	0.087 (4)	−0.083 (3)
C39	0.493 (15)	0.306 (9)	0.124 (4)	−0.295 (11)	0.035 (6)	−0.019 (5)

Geometric parameters (Å, º) top

O1—C1	1.3548 (19)	C23—H23C	0.96
O1—H1O1	0.89 (3)	C24—H24A	0.96
O2—C20	1.354 (2)	C24—H24B	0.96
O2—H1O2	0.87 (3)	C24—H24C	0.96
N1—C7	1.280 (2)	C25—C27	1.527 (3)
N1—C8	1.415 (2)	C25—C26	1.528 (3)
N2—C14	1.280 (2)	C25—C28	1.533 (3)
N2—C13	1.419 (2)	C26—H26A	0.96
C1—C6	1.399 (2)	C26—H26B	0.96
C1—C2	1.410 (2)	C26—H26C	0.96
C2—C3	1.385 (2)	C27—H27A	0.96
C2—C33	1.529 (2)	C27—H27B	0.96
C3—C4	1.394 (3)	C27—H27C	0.96
C3—H3A	0.93	C28—H28A	0.96
C4—C5	1.376 (2)	C28—H28B	0.96
C4—C21	1.531 (2)	C28—H28C	0.96
C5—C6	1.402 (2)	C29—C32	1.529 (3)
C5—H5A	0.93	C29—C30	1.532 (3)
C6—C7	1.449 (2)	C29—C31	1.533 (3)
C7—H7A	0.93	C30—H30A	0.96
C8—C9	1.388 (2)	C30—H30B	0.96
C8—C13	1.393 (2)	C30—H30C	0.96
C9—C10	1.384 (3)	C31—H31A	0.96
C9—H9A	0.93	C31—H31B	0.96
C10—C11	1.371 (3)	C31—H31C	0.96
C10—H10A	0.93	C32—H32A	0.96
C11—C12	1.379 (3)	C32—H32B	0.96
C11—H11A	0.93	C32—H32C	0.96
C12—C13	1.391 (2)	C33—C34	1.529 (3)
C12—H12A	0.93	C33—C36	1.534 (2)
C14—C15	1.448 (2)	C33—C35	1.538 (3)
C14—H14A	0.93	C34—H34A	0.96
C15—C16	1.401 (2)	C34—H34B	0.96
C15—C20	1.402 (2)	C34—H34C	0.96
C16—C17	1.374 (2)	C35—H35A	0.96
C16—H16A	0.93	C35—H35B	0.96
C17—C18	1.402 (2)	C35—H35C	0.96
C17—C25	1.534 (2)	C36—H36A	0.96
C18—C19	1.384 (2)	C36—H36B	0.96
C18—H18A	0.93	C36—H36C	0.96
C19—C20	1.406 (2)	O3—C38	1.111 (4)
C19—C29	1.535 (2)	C37—C38	1.456 (10)
C21—C24	1.507 (3)	C37—H37A	0.96
C21—C23	1.515 (3)	C37—H37B	0.96
C21—C22	1.530 (4)	C37—H37C	0.96
C22—H22A	0.96	C38—C39	1.444 (8)
C22—H22B	0.96	C39—H39A	0.96
C22—H22C	0.96	C39—H39B	0.96
C23—H23A	0.96	C39—H39C	0.96
C23—H23B	0.96

C1—O1—H1O1	105.8 (16)	C27—C25—C26	108.66 (19)
C20—O2—H1O2	104.6 (17)	C27—C25—C28	107.99 (17)
C7—N1—C8	119.31 (15)	C26—C25—C28	109.09 (18)
C14—N2—C13	119.35 (15)	C27—C25—C17	111.42 (16)
O1—C1—C6	119.97 (14)	C26—C25—C17	109.29 (15)
O1—C1—C2	119.56 (15)	C28—C25—C17	110.34 (16)
C6—C1—C2	120.47 (15)	C25—C26—H26A	109.5
C3—C2—C1	116.38 (15)	C25—C26—H26B	109.5
C3—C2—C33	122.46 (14)	H26A—C26—H26B	109.5
C1—C2—C33	121.16 (15)	C25—C26—H26C	109.5
C2—C3—C4	125.10 (15)	H26A—C26—H26C	109.5
C2—C3—H3A	117.5	H26B—C26—H26C	109.5
C4—C3—H3A	117.5	C25—C27—H27A	109.5
C5—C4—C3	116.75 (16)	C25—C27—H27B	109.5
C5—C4—C21	123.03 (17)	H27A—C27—H27B	109.5
C3—C4—C21	120.18 (16)	C25—C27—H27C	109.5
C4—C5—C6	121.45 (17)	H27A—C27—H27C	109.5
C4—C5—H5A	119.3	H27B—C27—H27C	109.5
C6—C5—H5A	119.3	C25—C28—H28A	109.5
C1—C6—C5	119.85 (15)	C25—C28—H28B	109.5
C1—C6—C7	121.48 (15)	H28A—C28—H28B	109.5
C5—C6—C7	118.57 (16)	C25—C28—H28C	109.5
N1—C7—C6	122.76 (16)	H28A—C28—H28C	109.5
N1—C7—H7A	118.6	H28B—C28—H28C	109.5
C6—C7—H7A	118.6	C32—C29—C30	107.16 (16)
C9—C8—C13	119.21 (16)	C32—C29—C31	107.54 (16)
C9—C8—N1	122.34 (16)	C30—C29—C31	110.67 (19)
C13—C8—N1	118.40 (14)	C32—C29—C19	112.08 (16)
C10—C9—C8	120.87 (18)	C30—C29—C19	109.44 (16)
C10—C9—H9A	119.6	C31—C29—C19	109.92 (16)
C8—C9—H9A	119.6	C29—C30—H30A	109.5
C11—C10—C9	119.65 (18)	C29—C30—H30B	109.5
C11—C10—H10A	120.2	H30A—C30—H30B	109.5
C9—C10—H10A	120.2	C29—C30—H30C	109.5
C10—C11—C12	120.33 (18)	H30A—C30—H30C	109.5
C10—C11—H11A	119.8	H30B—C30—H30C	109.5
C12—C11—H11A	119.8	C29—C31—H31A	109.5
C11—C12—C13	120.58 (18)	C29—C31—H31B	109.5
C11—C12—H12A	119.7	H31A—C31—H31B	109.5
C13—C12—H12A	119.7	C29—C31—H31C	109.5
C12—C13—C8	119.26 (16)	H31A—C31—H31C	109.5
C12—C13—N2	122.41 (16)	H31B—C31—H31C	109.5
C8—C13—N2	118.22 (14)	C29—C32—H32A	109.5
N2—C14—C15	122.85 (16)	C29—C32—H32B	109.5
N2—C14—H14A	118.6	H32A—C32—H32B	109.5
C15—C14—H14A	118.6	C29—C32—H32C	109.5
C16—C15—C20	119.76 (15)	H32A—C32—H32C	109.5
C16—C15—C14	118.42 (16)	H32B—C32—H32C	109.5
C20—C15—C14	121.81 (16)	C2—C33—C34	110.08 (15)
C17—C16—C15	121.63 (16)	C2—C33—C36	112.41 (15)
C17—C16—H16A	119.2	C34—C33—C36	107.34 (16)
C15—C16—H16A	119.2	C2—C33—C35	109.12 (16)
C16—C17—C18	116.59 (16)	C34—C33—C35	110.84 (18)
C16—C17—C25	123.30 (16)	C36—C33—C35	107.01 (16)
C18—C17—C25	120.08 (15)	C33—C34—H34A	109.5
C19—C18—C17	124.94 (16)	C33—C34—H34B	109.5
C19—C18—H18A	117.5	H34A—C34—H34B	109.5
C17—C18—H18A	117.5	C33—C34—H34C	109.5
C18—C19—C20	116.57 (15)	H34A—C34—H34C	109.5
C18—C19—C29	121.98 (15)	H34B—C34—H34C	109.5
C20—C19—C29	121.45 (15)	C33—C35—H35A	109.5
O2—C20—C15	119.90 (15)	C33—C35—H35B	109.5
O2—C20—C19	119.60 (15)	H35A—C35—H35B	109.5
C15—C20—C19	120.49 (16)	C33—C35—H35C	109.5
C24—C21—C23	111.8 (2)	H35A—C35—H35C	109.5
C24—C21—C22	107.3 (2)	H35B—C35—H35C	109.5
C23—C21—C22	107.7 (2)	C33—C36—H36A	109.5
C24—C21—C4	108.80 (17)	C33—C36—H36B	109.5
C23—C21—C4	110.02 (17)	H36A—C36—H36B	109.5
C22—C21—C4	111.11 (18)	C33—C36—H36C	109.5
C21—C22—H22A	109.5	H36A—C36—H36C	109.5
C21—C22—H22B	109.5	H36B—C36—H36C	109.5
H22A—C22—H22B	109.5	C38—C37—H37A	109.5
C21—C22—H22C	109.5	C38—C37—H37B	109.5
H22A—C22—H22C	109.5	H37A—C37—H37B	109.5
H22B—C22—H22C	109.5	C38—C37—H37C	109.5
C21—C23—H23A	109.5	H37A—C37—H37C	109.5
C21—C23—H23B	109.5	H37B—C37—H37C	109.5
H23A—C23—H23B	109.5	O3—C38—C39	132.8 (9)
C21—C23—H23C	109.5	O3—C38—C37	116.6 (8)
H23A—C23—H23C	109.5	C39—C38—C37	110.2 (6)
H23B—C23—H23C	109.5	C38—C39—H39A	109.5
C21—C24—H24A	109.5	C38—C39—H39B	109.5
C21—C24—H24B	109.5	H39A—C39—H39B	109.5
H24A—C24—H24B	109.5	C38—C39—H39C	109.5
C21—C24—H24C	109.5	H39A—C39—H39C	109.5
H24A—C24—H24C	109.5	H39B—C39—H39C	109.5
H24B—C24—H24C	109.5

O1—C1—C2—C3	−178.29 (15)	C15—C16—C17—C18	0.6 (3)
C6—C1—C2—C3	0.8 (2)	C15—C16—C17—C25	−177.69 (16)
O1—C1—C2—C33	1.3 (2)	C16—C17—C18—C19	−0.9 (3)
C6—C1—C2—C33	−179.58 (15)	C25—C17—C18—C19	177.48 (15)
C1—C2—C3—C4	−0.5 (2)	C17—C18—C19—C20	−0.1 (3)
C33—C2—C3—C4	179.91 (16)	C17—C18—C19—C29	179.91 (16)
C2—C3—C4—C5	−0.1 (3)	C16—C15—C20—O2	178.13 (16)
C2—C3—C4—C21	177.60 (16)	C14—C15—C20—O2	−0.6 (3)
C3—C4—C5—C6	0.4 (2)	C16—C15—C20—C19	−1.6 (3)
C21—C4—C5—C6	−177.27 (16)	C14—C15—C20—C19	179.70 (16)
O1—C1—C6—C5	178.51 (15)	C18—C19—C20—O2	−178.41 (15)
C2—C1—C6—C5	−0.6 (2)	C29—C19—C20—O2	1.6 (2)
O1—C1—C6—C7	2.0 (2)	C18—C19—C20—C15	1.3 (2)
C2—C1—C6—C7	−177.09 (15)	C29—C19—C20—C15	−178.68 (16)
C4—C5—C6—C1	0.0 (3)	C5—C4—C21—C24	107.0 (2)
C4—C5—C6—C7	176.58 (16)	C3—C4—C21—C24	−70.5 (2)
C8—N1—C7—C6	178.16 (15)	C5—C4—C21—C23	−130.1 (2)
C1—C6—C7—N1	0.5 (3)	C3—C4—C21—C23	52.3 (3)
C5—C6—C7—N1	−176.03 (16)	C5—C4—C21—C22	−10.9 (3)
C7—N1—C8—C9	45.8 (3)	C3—C4—C21—C22	171.5 (2)
C7—N1—C8—C13	−136.81 (18)	C16—C17—C25—C27	−5.8 (2)
C13—C8—C9—C10	2.9 (3)	C18—C17—C25—C27	176.03 (17)
N1—C8—C9—C10	−179.8 (2)	C16—C17—C25—C26	114.3 (2)
C8—C9—C10—C11	−0.2 (4)	C18—C17—C25—C26	−63.9 (2)
C9—C10—C11—C12	−1.5 (4)	C16—C17—C25—C28	−125.7 (2)
C10—C11—C12—C13	0.6 (4)	C18—C17—C25—C28	56.1 (2)
C11—C12—C13—C8	2.0 (3)	C18—C19—C29—C32	−0.8 (2)
C11—C12—C13—N2	178.2 (2)	C20—C19—C29—C32	179.21 (16)
C9—C8—C13—C12	−3.7 (3)	C18—C19—C29—C30	−119.52 (19)
N1—C8—C13—C12	178.86 (17)	C20—C19—C29—C30	60.5 (2)
C9—C8—C13—N2	180.00 (18)	C18—C19—C29—C31	118.74 (19)
N1—C8—C13—N2	2.6 (3)	C20—C19—C29—C31	−61.3 (2)
C14—N2—C13—C12	45.9 (3)	C3—C2—C33—C34	119.17 (19)
C14—N2—C13—C8	−137.91 (18)	C1—C2—C33—C34	−60.4 (2)
C13—N2—C14—C15	−178.34 (16)	C3—C2—C33—C36	−0.4 (2)
N2—C14—C15—C16	−175.52 (17)	C1—C2—C33—C36	179.98 (16)
N2—C14—C15—C20	3.2 (3)	C3—C2—C33—C35	−118.98 (18)
C20—C15—C16—C17	0.6 (3)	C1—C2—C33—C35	61.4 (2)
C14—C15—C16—C17	179.36 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···N1	0.89 (2)	1.76 (3)	2.5809 (19)	153 (3)
O2—H1O2···N2	0.87 (3)	1.78 (3)	2.5956 (19)	155 (3)
C7—H7A···O3	0.93	2.58	3.460 (6)	158
C30—H30B···O2	0.96	2.36	2.994 (3)	123
C31—H31A···O2	0.96	2.34	2.989 (3)	124
C34—H34C···O1	0.96	2.32	2.968 (3)	124
C35—H35A···O1	0.96	2.35	2.996 (3)	124
C24—H24B···Cg2ⁱ	0.96	2.97	3.877 (3)	158
C26—H26A···Cg1ⁱⁱ	0.96	2.89	3.798 (2)	157

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

Experimental details

Crystal data
Chemical formula	C₃₆H₄₈N₂O₂·C₃H₆O
M_r	598.84
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	10.0008 (2), 12.0020 (3), 17.0366 (4)
α, β, γ (°)	82.068 (1), 86.320 (1), 65.764 (1)
V (Å³)	1846.76 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.59 × 0.55 × 0.43

Data collection
Diffractometer	Bruker SMART APEX2 CCD area-detecto diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.962, 0.972
No. of measured, independent and observed [I > 2σ(I)] reflections	26090, 8384, 5874
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.183, 1.04
No. of reflections	8384
No. of parameters	419
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.28

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···N1	0.89 (2)	1.76 (3)	2.5809 (19)	153 (3)
O2—H1O2···N2	0.87 (3)	1.78 (3)	2.5956 (19)	155 (3)
C7—H7A···O3	0.93	2.58	3.460 (6)	158
C30—H30B···O2	0.96	2.36	2.994 (3)	123
C31—H31A···O2	0.96	2.34	2.989 (3)	124
C34—H34C···O1	0.96	2.32	2.968 (3)	124
C35—H35A···O1	0.96	2.35	2.996 (3)	124
C24—H24B···Cg2ⁱ	0.96	2.97	3.877 (3)	158
C26—H26A···Cg1ⁱⁱ	0.96	2.89	3.798 (2)	157

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

Footnotes

‡On study leave from: International University of Africa, Sudan. E-mail: nasertaha90@hotmail.com.

§Additional correspondence author. E-mail: suchada.c@psu.ac.th.

Acknowledgements

The authors thank the Malaysian Government, the Ministry of Science, Technology and Innovation, Malaysia (MOSTI), and Universiti Sains Malaysia for the E-Science Fund research grant (PKIMIA/613308) and facilities. The International University of Africa (Sudan) is acknowledged for providing study leave to NEE. The authors also thank Universiti Sains Malaysia for the Fundamental Research Grant Scheme (FRGS) grant No. 203/PFIZIK/671064.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–S19. CrossRef Web of Science Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chamg, N.-L. (1995). Angew. Chem. Int. Ed. Eng1. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dao, V.-T., Gaspard, C., Mayer, M., Werner, G. H., Nguyen, S. N. & Michelot, R. J. (2000). Eur. J. Med. Chem. 35, 805–813. Web of Science CrossRef PubMed CAS Google Scholar
Eltayeb, N. E. & Ahmed, T. A. (2005a). J. Sci. Tech. 6, 51–59. Google Scholar
Eltayeb, N. E. & Ahmed, T. A. (2005b). Sudan J. Basic Sci. 7, 97–108. Google Scholar
Eltayeb, N. E., Teoh, S. G., Chantrapromma, S., Fun, H.-K. & Ibrahim, K. (2007). Acta Cryst. E63, m2024–m2025. Web of Science CSD CrossRef IUCr Journals Google Scholar
Eltayeb, N. E., Teoh, S. G., Teh, J. B.-J., Fun, H.-K. & Ibrahim, K. (2007a). Acta Cryst. E63, o695–o696. Web of Science CSD CrossRef IUCr Journals Google Scholar
Eltayeb, N. E., Teoh, S. G., Teh, J. B.-J., Fun, H.-K. & Ibrahim, K. (2007b). Acta Cryst. E63, o766–o767. Web of Science CSD CrossRef IUCr Journals Google Scholar
Karthikeyan, M. S., Prasad, D. J., Poojary, B., Bhat, K. S., Holla, B. S. & Kumari, N. S. (2006). Bioorg. Med. Chem. 14, 7482–7489. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sriram, D., Yogeeswari, P., Myneedu, N. S. & Saraswat, V. (2006). Bioorg. Med. Chem. Lett. 16, 2127–2129. Web of Science CrossRef PubMed CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.