6,6′-Di-tert-butyl-2,2′-[1,2-phenyl­ene­bis(nitrilo­methyl­idyne)]diphenol

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

doi:10.1107/S1600536809048922

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 12| December 2009| Pages o3142-o3143

doi:10.1107/S1600536809048922

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6,6′-Di-tert-butyl-2,2′-[1,2-phenylenebis(nitrilomethylidyne)]diphenol

Naser Eltaher Eltayeb,^a ‡ Siang Guan Teoh,^a Chin Sing Yeap,^b § Hoong-Kun Fun ^b ^*¶ and Rohana Adnan ^a

^aSchool of Chemical Science, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 12 November 2009; accepted 17 November 2009; online 21 November 2009)

The molecule of the title Schiff base compound, C₂₈H₃₂N₂O₂, has a twisted geometry, the dihedral angles between the central benzene ring and the other two benzene rings being 29.12 (14) and 26.01 (14)°. Four intramolecular C—H⋯O hydrogen bonds and two intramolecular O—H⋯N hydrogen bonds stabilize the molecular structure. In the crystal packing, molecules are stacked along the a axis and stabilized by π–π interactions [centroid–centroid distance = 3.6724 (17) Å]. The crystal studied was found to be a non-merohedral twin, the refined ratio of twin components being 0.374 (5):0.626 (5).

Related literature

For biological applications of Schiff base derivatives, see: Dao et al. (2000 ); Eltayeb & Ahmed (2005a ,b ); Karthikeyan et al. (2006 ); Sriram et al. (2006 ). For related structures, see: Eltayeb et al. (2007a ,b ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₈H₃₂N₂O₂
M_r = 428.56
Triclinic, $[P \overline 1]$
a = 6.8312 (9) Å
b = 13.9632 (16) Å
c = 14.0689 (15) Å
α = 116.615 (5)°
β = 99.068 (4)°
γ = 98.209 (4)°
V = 1149.6 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.87 × 0.20 × 0.05 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.936, T_max = 0.996
4021 measured reflections
4021 independent reflections
3241 reflections with I > 2σ(I)

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.206
S = 1.19
4021 reflections
304 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O2⋯N2	0.91 (5)	1.73 (4)	2.584 (3)	156 (4)
O1—H1O1⋯N1	0.91 (5)	1.77 (6)	2.609 (3)	151 (5)
C22—H22A⋯O1	0.96	2.34	2.993 (3)	125
C23—H23A⋯O1	0.96	2.34	2.987 (4)	124
C26—H26B⋯O2	0.96	2.31	2.963 (4)	125
C27—H27C⋯O2	0.96	2.37	3.011 (4)	124

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; 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, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809048922/lh2954sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809048922/lh2954Isup2.hkl

checkCIF report

Comment top

Schiff bases have received much attention because of their potential applications with some of these compounds exhibiting various pharmacological activities, as noted by their 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). Previously, 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-tert-butyl-2-hydroxybenzaldehyde.

The title compound (Fig. 1) has a slightly twisted geometry with the dihedral angles between the two benzene rings (C1–C6 and C15–C20) with the central benzene ring (C8–C13) being 29.12 (14) and 26.01 (14)°. The geometrical parameters are comparable to previously reported structures (Eltayeb et al., 2007a,b). Two bifurcated intramolecular C—H···O hydrogen bonds and two intramolecular O—H···N hydrogen bonds stabilized the molecular structure (Fig. 1, Table 1). In the crystal packing (Fig. 2), the molecules are stacked along the a axis and stabilized by Cg1···Cg1 = 3.6724 (17) Å interactions [Cg1 is the centroid of C1–C6 phenyl ring; 1 - x, -y, 1 - z].

Related literature top

For biological applications of Schiff base derivatives, see: Dao et al. (2000); Eltayeb & Ahmed (2005a,b); Karthikeyan et al. (2006); Sriram et al. (2006). For related structures, see: Eltayeb et al. (2007a,b). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

To a solution of o-phenylenediamine (0.216 g, 2 mmol) in ethanol (20 ml) was added 3-tert-butyl-2-hydroxybenzaldehyde (0.7 ml, 4 mmol). The mixture was refluxed with stirring for 30 min. The resultant orange solution was filtered. Yellow precipitate obtained was dissolved in acetone. Yellow crystals suitable for XRD formed after a few days of slow evaporation of the solvent at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (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, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with 50% probability ellipsoids for non-H atoms. Intramolecular hydrogen bonds are shown as dashed lines.
	Fig. 2. The crystal packing of the title compound, viewed along the a axis, showing how the molecules are stacked along the a axis.

6,6'-Di-tert-butyl-2,2'-[1,2-phenylenebis(nitrilomethylidyne)]diphenol top

Crystal data top

C₂₈H₃₂N₂O₂	Z = 2
M_r = 428.56	F(000) = 460
Triclinic, P1	D_x = 1.238 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8312 (9) Å	Cell parameters from 4325 reflections
b = 13.9632 (16) Å	θ = 2.9–29.9°
c = 14.0689 (15) Å	µ = 0.08 mm⁻¹
α = 116.615 (5)°	T = 100 K
β = 99.068 (4)°	Plate, yellow
γ = 98.209 (4)°	0.87 × 0.20 × 0.05 mm
V = 1149.6 (2) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4021 independent reflections
Radiation source: fine-focus sealed tube	3241 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.000
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→7
T_min = 0.936, T_max = 0.996	k = −16→14
4021 measured reflections	l = −4→16

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.206	H atoms treated by a mixture of independent and constrained refinement
S = 1.19	w = 1/[σ²(F_o²) + (0.0995P)² + 0.5885P] where P = (F_o² + 2F_c²)/3
4021 reflections	(Δ/σ)_max < 0.001
304 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₂₈H₃₂N₂O₂	γ = 98.209 (4)°
M_r = 428.56	V = 1149.6 (2) Å³
Triclinic, P1	Z = 2
a = 6.8312 (9) Å	Mo Kα radiation
b = 13.9632 (16) Å	µ = 0.08 mm⁻¹
c = 14.0689 (15) Å	T = 100 K
α = 116.615 (5)°	0.87 × 0.20 × 0.05 mm
β = 99.068 (4)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4021 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3241 reflections with I > 2σ(I)
T_min = 0.936, T_max = 0.996	R_int = 0.000
4021 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.206	H atoms treated by a mixture of independent and constrained refinement
S = 1.19	Δρ_max = 0.32 e Å⁻³
4021 reflections	Δρ_min = −0.39 e Å⁻³
304 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.2350 (3)	0.09518 (15)	0.37885 (15)	0.0209 (5)
O2	−0.1083 (3)	0.11123 (16)	0.22061 (15)	0.0231 (5)
N1	0.0669 (3)	−0.11626 (17)	0.27055 (17)	0.0176 (5)
N2	−0.1856 (3)	−0.10123 (17)	0.10607 (18)	0.0177 (5)
C1	0.2757 (4)	0.0859 (2)	0.4710 (2)	0.0173 (6)
C2	0.3650 (4)	0.1817 (2)	0.5735 (2)	0.0180 (6)
C3	0.4083 (4)	0.1661 (2)	0.6647 (2)	0.0205 (6)
H3A	0.4711	0.2275	0.7327	0.025*
C4	0.3624 (4)	0.0631 (2)	0.6593 (2)	0.0213 (6)
H4A	0.3953	0.0565	0.7225	0.026*
C5	0.2682 (4)	−0.0287 (2)	0.5601 (2)	0.0185 (6)
H5A	0.2332	−0.0975	0.5562	0.022*
C6	0.2250 (4)	−0.0188 (2)	0.4652 (2)	0.0166 (6)
C7	0.1138 (4)	−0.1159 (2)	0.3629 (2)	0.0178 (6)
H7A	0.0740	−0.1818	0.3641	0.021*
C8	−0.0515 (4)	−0.2150 (2)	0.1771 (2)	0.0164 (6)
C9	−0.0387 (4)	−0.3197 (2)	0.1618 (2)	0.0209 (6)
H9A	0.0541	−0.3258	0.2136	0.025*
C10	−0.1613 (5)	−0.4144 (2)	0.0713 (2)	0.0246 (7)
H10A	−0.1506	−0.4834	0.0624	0.029*
C11	−0.3008 (5)	−0.4060 (2)	−0.0064 (2)	0.0239 (7)
H11A	−0.3866	−0.4694	−0.0663	0.029*
C12	−0.3115 (4)	−0.3039 (2)	0.0056 (2)	0.0211 (6)
H12A	−0.4059	−0.2991	−0.0465	0.025*
C13	−0.1838 (4)	−0.2070 (2)	0.0942 (2)	0.0174 (6)
C14	−0.2331 (4)	−0.0902 (2)	0.0202 (2)	0.0191 (6)
H14A	−0.2692	−0.1530	−0.0484	0.023*
C15	−0.2329 (4)	0.0154 (2)	0.0251 (2)	0.0181 (6)
C16	−0.2928 (4)	0.0202 (2)	−0.0721 (2)	0.0218 (6)
H16A	−0.3379	−0.0447	−0.1389	0.026*
C17	−0.2855 (4)	0.1196 (2)	−0.0698 (2)	0.0232 (6)
H17A	−0.3291	0.1223	−0.1344	0.028*
C18	−0.2127 (4)	0.2166 (2)	0.0297 (2)	0.0222 (6)
H18A	−0.2052	0.2835	0.0296	0.027*
C19	−0.1506 (4)	0.2182 (2)	0.1293 (2)	0.0202 (6)
C20	−0.1651 (4)	0.1147 (2)	0.1261 (2)	0.0187 (6)
C21	0.4042 (4)	0.2968 (2)	0.5821 (2)	0.0218 (6)
C22	0.2009 (4)	0.3178 (2)	0.5415 (2)	0.0241 (6)
H22A	0.1358	0.2601	0.4681	0.036*
H22B	0.2262	0.3876	0.5421	0.036*
H22C	0.1134	0.3191	0.5890	0.036*
C23	0.5547 (5)	0.3065 (2)	0.5150 (2)	0.0265 (7)
H23A	0.5013	0.2504	0.4397	0.040*
H23B	0.6834	0.2972	0.5439	0.040*
H23C	0.5739	0.3779	0.5194	0.040*
C24	0.4951 (5)	0.3884 (2)	0.7013 (2)	0.0271 (7)
H24A	0.6252	0.3795	0.7290	0.041*
H24B	0.4044	0.3838	0.7456	0.041*
H24C	0.5125	0.4591	0.7040	0.041*
C25	−0.0608 (5)	0.3263 (2)	0.2379 (2)	0.0237 (7)
C26	−0.1878 (5)	0.3344 (2)	0.3208 (3)	0.0306 (7)
H26A	−0.1278	0.4014	0.3887	0.046*
H26B	−0.1901	0.2723	0.3336	0.046*
H26C	−0.3248	0.3346	0.2921	0.046*
C27	0.1622 (5)	0.3313 (2)	0.2836 (2)	0.0263 (7)
H27A	0.2176	0.3976	0.3526	0.039*
H27B	0.2406	0.3311	0.2326	0.039*
H27C	0.1676	0.2683	0.2941	0.039*
C28	−0.0596 (5)	0.4277 (2)	0.2213 (3)	0.0299 (7)
H28A	−0.0024	0.4936	0.2905	0.045*
H28B	−0.1970	0.4272	0.1922	0.045*
H28C	0.0213	0.4258	0.1708	0.045*
H1O2	−0.127 (6)	0.038 (3)	0.199 (3)	0.049 (11)*
H1O1	0.174 (7)	0.026 (4)	0.322 (4)	0.064 (13)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0261 (11)	0.0191 (10)	0.0153 (9)	0.0031 (8)	0.0029 (8)	0.0079 (8)
O2	0.0313 (12)	0.0210 (10)	0.0194 (10)	0.0070 (9)	0.0042 (9)	0.0120 (8)
N1	0.0133 (12)	0.0176 (11)	0.0192 (12)	0.0036 (9)	0.0042 (9)	0.0066 (9)
N2	0.0142 (12)	0.0192 (11)	0.0206 (12)	0.0052 (9)	0.0042 (9)	0.0100 (9)
C1	0.0108 (13)	0.0255 (14)	0.0159 (13)	0.0061 (11)	0.0040 (10)	0.0095 (11)
C2	0.0105 (13)	0.0226 (14)	0.0186 (13)	0.0040 (11)	0.0057 (11)	0.0073 (11)
C3	0.0140 (14)	0.0250 (14)	0.0155 (13)	0.0033 (11)	0.0043 (11)	0.0040 (11)
C4	0.0170 (14)	0.0312 (15)	0.0175 (13)	0.0082 (12)	0.0051 (11)	0.0124 (12)
C5	0.0129 (14)	0.0247 (14)	0.0210 (14)	0.0081 (11)	0.0061 (11)	0.0120 (12)
C6	0.0088 (13)	0.0213 (13)	0.0201 (13)	0.0059 (10)	0.0053 (11)	0.0091 (11)
C7	0.0149 (14)	0.0201 (13)	0.0200 (14)	0.0065 (11)	0.0060 (11)	0.0098 (11)
C8	0.0130 (13)	0.0161 (13)	0.0179 (13)	0.0022 (10)	0.0063 (11)	0.0059 (11)
C9	0.0230 (15)	0.0227 (14)	0.0197 (14)	0.0091 (12)	0.0070 (12)	0.0110 (12)
C10	0.0336 (17)	0.0151 (13)	0.0249 (15)	0.0064 (12)	0.0109 (13)	0.0083 (12)
C11	0.0262 (16)	0.0192 (14)	0.0178 (14)	−0.0017 (12)	0.0055 (12)	0.0038 (11)
C12	0.0182 (14)	0.0250 (14)	0.0179 (13)	0.0028 (11)	0.0039 (11)	0.0094 (11)
C13	0.0136 (13)	0.0196 (13)	0.0185 (13)	0.0037 (11)	0.0073 (11)	0.0078 (11)
C14	0.0119 (13)	0.0232 (14)	0.0187 (13)	0.0024 (11)	0.0033 (11)	0.0079 (11)
C15	0.0096 (13)	0.0277 (14)	0.0202 (13)	0.0060 (11)	0.0044 (11)	0.0135 (12)
C16	0.0131 (14)	0.0320 (15)	0.0196 (14)	0.0044 (12)	0.0051 (11)	0.0117 (12)
C17	0.0135 (14)	0.0402 (16)	0.0265 (15)	0.0080 (12)	0.0063 (12)	0.0239 (13)
C18	0.0181 (14)	0.0298 (15)	0.0296 (15)	0.0107 (12)	0.0102 (12)	0.0206 (13)
C19	0.0142 (14)	0.0263 (14)	0.0264 (15)	0.0085 (11)	0.0091 (11)	0.0155 (12)
C20	0.0142 (14)	0.0270 (14)	0.0204 (14)	0.0077 (11)	0.0066 (11)	0.0146 (12)
C21	0.0194 (15)	0.0212 (14)	0.0217 (14)	0.0041 (11)	0.0068 (12)	0.0075 (12)
C22	0.0253 (16)	0.0233 (14)	0.0261 (15)	0.0075 (12)	0.0067 (13)	0.0133 (12)
C23	0.0259 (16)	0.0224 (14)	0.0274 (15)	0.0021 (12)	0.0087 (13)	0.0092 (12)
C24	0.0244 (16)	0.0227 (15)	0.0251 (15)	0.0022 (12)	0.0055 (13)	0.0052 (12)
C25	0.0277 (17)	0.0226 (14)	0.0257 (15)	0.0091 (12)	0.0104 (13)	0.0137 (12)
C26	0.0370 (19)	0.0291 (16)	0.0318 (16)	0.0139 (14)	0.0166 (15)	0.0156 (14)
C27	0.0267 (16)	0.0241 (14)	0.0245 (15)	0.0036 (12)	0.0049 (13)	0.0100 (12)
C28	0.0356 (18)	0.0275 (15)	0.0342 (17)	0.0111 (14)	0.0140 (14)	0.0185 (14)

Geometric parameters (Å, º) top

O1—C1	1.349 (3)	C15—C20	1.413 (4)
O1—H1O1	0.91 (4)	C16—C17	1.368 (4)
O2—C20	1.350 (3)	C16—H16A	0.9300
O2—H1O2	0.91 (4)	C17—C18	1.389 (4)
N1—C7	1.286 (3)	C17—H17A	0.9300
N1—C8	1.416 (3)	C18—C19	1.387 (4)
N2—C14	1.284 (3)	C18—H18A	0.9300
N2—C13	1.412 (3)	C19—C20	1.414 (4)
C1—C2	1.415 (4)	C19—C25	1.538 (4)
C1—C6	1.416 (4)	C21—C23	1.531 (4)
C2—C3	1.389 (4)	C21—C24	1.536 (4)
C2—C21	1.537 (4)	C21—C22	1.536 (4)
C3—C4	1.393 (4)	C22—H22A	0.9600
C3—H3A	0.9300	C22—H22B	0.9600
C4—C5	1.372 (4)	C22—H22C	0.9600
C4—H4A	0.9300	C23—H23A	0.9600
C5—C6	1.395 (4)	C23—H23B	0.9600
C5—H5A	0.9300	C23—H23C	0.9600
C6—C7	1.449 (4)	C24—H24A	0.9600
C7—H7A	0.9300	C24—H24B	0.9600
C8—C9	1.397 (4)	C24—H24C	0.9600
C8—C13	1.416 (4)	C25—C28	1.534 (4)
C9—C10	1.383 (4)	C25—C26	1.535 (4)
C9—H9A	0.9300	C25—C27	1.536 (4)
C10—C11	1.391 (4)	C26—H26A	0.9600
C10—H10A	0.9300	C26—H26B	0.9600
C11—C12	1.373 (4)	C26—H26C	0.9600
C11—H11A	0.9300	C27—H27A	0.9600
C12—C13	1.398 (4)	C27—H27B	0.9600
C12—H12A	0.9300	C27—H27C	0.9600
C14—C15	1.445 (4)	C28—H28A	0.9600
C14—H14A	0.9300	C28—H28B	0.9600
C15—C16	1.399 (4)	C28—H28C	0.9600

C1—O1—H1O1	107 (3)	C19—C18—H18A	118.5
C20—O2—H1O2	104 (2)	C17—C18—H18A	118.5
C7—N1—C8	118.6 (2)	C18—C19—C20	116.7 (2)
C14—N2—C13	119.5 (2)	C18—C19—C25	122.3 (2)
O1—C1—C2	119.7 (2)	C20—C19—C25	120.9 (2)
O1—C1—C6	120.1 (2)	O2—C20—C15	119.8 (2)
C2—C1—C6	120.3 (2)	O2—C20—C19	119.3 (2)
C3—C2—C1	116.8 (2)	C15—C20—C19	120.9 (2)
C3—C2—C21	122.5 (2)	C23—C21—C24	107.6 (2)
C1—C2—C21	120.7 (2)	C23—C21—C22	110.5 (2)
C2—C3—C4	123.2 (2)	C24—C21—C22	106.9 (2)
C2—C3—H3A	118.4	C23—C21—C2	110.6 (2)
C4—C3—H3A	118.4	C24—C21—C2	111.7 (2)
C5—C4—C3	119.5 (3)	C22—C21—C2	109.4 (2)
C5—C4—H4A	120.2	C21—C22—H22A	109.5
C3—C4—H4A	120.2	C21—C22—H22B	109.5
C4—C5—C6	119.9 (2)	H22A—C22—H22B	109.5
C4—C5—H5A	120.1	C21—C22—H22C	109.5
C6—C5—H5A	120.0	H22A—C22—H22C	109.5
C5—C6—C1	120.2 (2)	H22B—C22—H22C	109.5
C5—C6—C7	118.6 (2)	C21—C23—H23A	109.5
C1—C6—C7	121.0 (2)	C21—C23—H23B	109.5
N1—C7—C6	123.8 (2)	H23A—C23—H23B	109.5
N1—C7—H7A	118.1	C21—C23—H23C	109.5
C6—C7—H7A	118.1	H23A—C23—H23C	109.5
C9—C8—C13	118.7 (2)	H23B—C23—H23C	109.5
C9—C8—N1	122.9 (2)	C21—C24—H24A	109.5
C13—C8—N1	118.4 (2)	C21—C24—H24B	109.5
C10—C9—C8	121.3 (3)	H24A—C24—H24B	109.5
C10—C9—H9A	119.4	C21—C24—H24C	109.5
C8—C9—H9A	119.4	H24A—C24—H24C	109.5
C9—C10—C11	119.7 (2)	H24B—C24—H24C	109.5
C9—C10—H10A	120.1	C28—C25—C26	107.5 (2)
C11—C10—H10A	120.1	C28—C25—C27	107.1 (2)
C12—C11—C10	119.8 (3)	C26—C25—C27	110.9 (2)
C12—C11—H11A	120.1	C28—C25—C19	111.6 (2)
C10—C11—H11A	120.1	C26—C25—C19	110.5 (2)
C11—C12—C13	121.6 (3)	C27—C25—C19	109.2 (2)
C11—C12—H12A	119.2	C25—C26—H26A	109.5
C13—C12—H12A	119.2	C25—C26—H26B	109.5
C12—C13—N2	122.8 (2)	H26A—C26—H26B	109.5
C12—C13—C8	118.6 (2)	C25—C26—H26C	109.5
N2—C13—C8	118.6 (2)	H26A—C26—H26C	109.5
N2—C14—C15	122.9 (2)	H26B—C26—H26C	109.5
N2—C14—H14A	118.5	C25—C27—H27A	109.5
C15—C14—H14A	118.5	C25—C27—H27B	109.5
C16—C15—C20	119.2 (2)	H27A—C27—H27B	109.5
C16—C15—C14	119.5 (2)	C25—C27—H27C	109.5
C20—C15—C14	121.3 (2)	H27A—C27—H27C	109.5
C17—C16—C15	120.5 (3)	H27B—C27—H27C	109.5
C17—C16—H16A	119.8	C25—C28—H28A	109.5
C15—C16—H16A	119.8	C25—C28—H28B	109.5
C16—C17—C18	119.6 (3)	H28A—C28—H28B	109.5
C16—C17—H17A	120.2	C25—C28—H28C	109.5
C18—C17—H17A	120.2	H28A—C28—H28C	109.5
C19—C18—C17	123.1 (3)	H28B—C28—H28C	109.5

O1—C1—C2—C3	−178.2 (2)	N1—C8—C13—N2	2.6 (4)
C6—C1—C2—C3	3.2 (4)	C13—N2—C14—C15	−178.2 (2)
O1—C1—C2—C21	3.7 (4)	N2—C14—C15—C16	−178.0 (3)
C6—C1—C2—C21	−174.9 (2)	N2—C14—C15—C20	4.8 (4)
C1—C2—C3—C4	−2.1 (4)	C20—C15—C16—C17	0.1 (4)
C21—C2—C3—C4	176.0 (2)	C14—C15—C16—C17	−177.2 (2)
C2—C3—C4—C5	−0.5 (4)	C15—C16—C17—C18	1.8 (4)
C3—C4—C5—C6	2.0 (4)	C16—C17—C18—C19	−1.8 (4)
C4—C5—C6—C1	−0.8 (4)	C17—C18—C19—C20	−0.2 (4)
C4—C5—C6—C7	−176.1 (2)	C17—C18—C19—C25	177.0 (3)
O1—C1—C6—C5	179.5 (2)	C16—C15—C20—O2	179.5 (2)
C2—C1—C6—C5	−1.9 (4)	C14—C15—C20—O2	−3.2 (4)
O1—C1—C6—C7	−5.3 (4)	C16—C15—C20—C19	−2.2 (4)
C2—C1—C6—C7	173.3 (2)	C14—C15—C20—C19	175.1 (2)
C8—N1—C7—C6	−176.7 (2)	C18—C19—C20—O2	−179.5 (2)
C5—C6—C7—N1	−179.6 (3)	C25—C19—C20—O2	3.2 (4)
C1—C6—C7—N1	5.2 (4)	C18—C19—C20—C15	2.2 (4)
C7—N1—C8—C9	−32.3 (4)	C25—C19—C20—C15	−175.1 (2)
C7—N1—C8—C13	149.7 (2)	C3—C2—C21—C23	120.0 (3)
C13—C8—C9—C10	−4.1 (4)	C1—C2—C21—C23	−62.0 (3)
N1—C8—C9—C10	177.9 (2)	C3—C2—C21—C24	0.1 (4)
C8—C9—C10—C11	−0.1 (4)	C1—C2—C21—C24	178.1 (2)
C9—C10—C11—C12	2.0 (4)	C3—C2—C21—C22	−118.1 (3)
C10—C11—C12—C13	0.5 (4)	C1—C2—C21—C22	59.9 (3)
C11—C12—C13—N2	177.3 (2)	C18—C19—C25—C28	2.6 (4)
C11—C12—C13—C8	−4.7 (4)	C20—C19—C25—C28	179.7 (2)
C14—N2—C13—C12	−29.9 (4)	C18—C19—C25—C26	122.2 (3)
C14—N2—C13—C8	152.0 (3)	C20—C19—C25—C26	−60.7 (3)
C9—C8—C13—C12	6.4 (4)	C18—C19—C25—C27	−115.6 (3)
N1—C8—C13—C12	−175.6 (2)	C20—C19—C25—C27	61.5 (3)
C9—C8—C13—N2	−175.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···N2	0.91 (5)	1.73 (4)	2.584 (3)	156 (4)
O1—H1O1···N1	0.91 (5)	1.77 (6)	2.609 (3)	151 (5)
C22—H22A···O1	0.96	2.34	2.993 (3)	125
C23—H23A···O1	0.96	2.34	2.987 (4)	124
C26—H26B···O2	0.96	2.31	2.963 (4)	125
C27—H27C···O2	0.96	2.37	3.011 (4)	124

Experimental details

Crystal data
Chemical formula	C₂₈H₃₂N₂O₂
M_r	428.56
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	6.8312 (9), 13.9632 (16), 14.0689 (15)
α, β, γ (°)	116.615 (5), 99.068 (4), 98.209 (4)
V (Å³)	1149.6 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.87 × 0.20 × 0.05

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.936, 0.996
No. of measured, independent and observed [I > 2σ(I)] reflections	4021, 4021, 3241
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.206, 1.19
No. of reflections	4021
No. of parameters	304
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.39

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···N2	0.91 (5)	1.73 (4)	2.584 (3)	156 (4)
O1—H1O1···N1	0.91 (5)	1.77 (6)	2.609 (3)	151 (5)
C22—H22A···O1	0.9600	2.3400	2.993 (3)	125.00
C23—H23A···O1	0.9600	2.3400	2.987 (4)	124.00
C26—H26B···O2	0.9600	2.3100	2.963 (4)	125.00
C27—H27C···O2	0.9600	2.3700	3.011 (4)	124.00

Footnotes

‡Current address: Department of Chemistry, International University of Africa, Khartoum, Sudan. E-mail: nasertaha90@hotmail.com.

§Thomson Reuters ResearcherID: A-5523-2009.

¶Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors thank the Malaysian Government, the Ministry of Higher Education, (MOHE) and Universiti Sains Malaysia (USM) for the FRGS and RU research grants (PKIMIA/815002 and PKIMIA/811120). The International University of Africa (Sudan) is acknowledged for providing study leave to NEE. HKF and CSY thank USM for the Research University Golden Goose grant (1001/PFIZIK/811012). CSY thanks USM for the award of a USM Fellowship.

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