(E)-N′-(2-Hydroxy­benzyl­idene)-2-(4-isobutyl­phen­yl)propanohydrazide

Goh, J.H.; Fun, H.-K.; Vinayaka, A.C.; Kalluraya, B.

doi:10.1107/S1600536809050971

organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o24

doi:10.1107/S1600536809050971

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(E)-N′-(2-Hydroxybenzylidene)-2-(4-isobutylphenyl)propanohydrazide

Jia Hao Goh,^a ‡ Hoong-Kun Fun,^a ^*§ A. C. Vinayaka ^b and B. Kalluraya ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India
^*Correspondence e-mail: hkfun@usm.my

(Received 25 November 2009; accepted 26 November 2009; online 4 December 2009)

The title hydrazide compound, C₂₀H₂₄N₂O₂, exists in a trans configuration with respect to the acyclic C=N bond and an intramolecular O—H⋯N hydrogen bond generates an S(6) ring motif. The mean plane through the formohydrazide unit is essentially planar [maximum deviation = 0.025 (2) Å], and forms dihedral angles of 24.45 (16) and 87.14 (16)° with the two benzene rings. In the crystal structure, intermolecular N—H⋯O and C—H⋯O hydrogen bonds link neighbouring molecules into extended chains along the c axis, which incorporate R₂²(16) ring motifs. An intermolecular C—H⋯π interaction is also observed.

Related literature

For the metal coordination and pharmacological activity of the title compound, see: Bedia et al. (2006 ); Rodrìguez-Argüelles et al. (2004 ); Rollas et al. (2002 ); Terzioglu & Gürsoy (2003 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For related structures, see: Fun et al. (2009a ,b ). For bond-length data, see: Allen et al. (1987 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₀H₂₄N₂O₂
M_r = 324.41
Monoclinic, P 2₁ /c
a = 5.5017 (2) Å
b = 33.0204 (14) Å
c = 9.7279 (4) Å
β = 91.731 (3)°
V = 1766.45 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.39 × 0.24 × 0.19 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.970, T_max = 0.985
18817 measured reflections
4059 independent reflections
3190 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.076
wR(F²) = 0.181
S = 1.18
4059 reflections
228 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O2ⁱ	0.87 (3)	1.96 (3)	2.790 (2)	159 (3)
O1—H1O1⋯N1	0.90 (4)	1.83 (4)	2.626 (3)	147 (4)
C14—H14A⋯O1ⁱ	0.93	2.51	3.272 (4)	139
C20—H20C⋯Cg1ⁱⁱ	0.96	2.80	3.722 (3)	161
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x+1, y, z. Cg1 is the centroid of the C10–C15 benzene ring.

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/S1600536809050971/hb5254sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809050971/hb5254Isup2.hkl

checkCIF report

Comment top

Hydrazone compounds are obtained by the reaction of aromatic and heterocyclic hydrazides with mono- and di-aldehydes or ketones and they have revealed very versatile behaviour in metal coordination (Rodrìguez-Argüelles et al., 2004). Hydrazones have been demonstrated to possess a variety of pharmacological activities (Bedia et al., 2006; Rollas et al., 2002; Terzioglu & Gürsoy, 2003). These observations have been the guidelines for the development of new hydrazone incorporating ibuprofen. Prompted by these observations and in continuation of our work (Fun et al., 2009b), we herein report the structure of this new hydrazone.

The title hydrazide compound (Fig. 1) exists in a trans configuration with respect to the acyclic C7═N1 bond. An intramolecular O1—H1O1···N1 hydrogen bond (Table 1) generates a six-membered ring, producing an S(6) ring motif (Bernstein et al., 1995). The mean plane through the formohydrazide unit (N1/N2/C8/O2) is essentially planar, with maximum deviation of 0.025 (2) Å for atom C8. This plane is inclined to the C1-C6 benzene ring at a dihedral angle of 24.45 (16)°, and almost perpendicular to the C10-C15 benzene ring, as indicated by the dihedral angle of 87.14 (16)°. The bond lengths and angles are within normal ranges and comparable to those closely related structures (Fun et al., 2009a,b).

In the crystal packing (Fig. 2), intermolecular N2—H1N2···O2 and C14—H14A···O1 hydrogen bonds (Table 1) link neighbouring molecules into one-dimensional infinite chains of R²₂(16) hydrogen bond ring motifs (Bernstein et al., 1995) along the c axis. An intermolecular C—H···π interaction (Table 1) involving the C10-C15 benzene ring is also observed.

Related literature top

For the metal coordination and pharmacological activity of the title compound, see: Bedia et al. (2006); Rodrìguez-Argüelles et al. (2004); Rollas et al. (2002); Terzioglu & Gürsoy (2003). For hydrogen-bond motifs, see: Bernstein et al. (1995). For related structures, see: Fun et al. (2009a,b). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986). Cg1 is the centroid of the C10–C15 benzene ring.

Experimental top

The title compound was obtained by refluxing for 1 h salicylaldehyde (0.01 mol), 2-(4-isobutylphenyl)propanehydrazide (0.01 mol) and ethanol (30 ml) with the addition of three drops of concentrated sulphuric acid. The solid product obtained was filtered, washed with ethanol and dried. Colourless blocks of (I) were obtained by slow evaporation from ethanol. Yield was 74 %. M.p. 426 K.

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 (I), showing 50% probability displacement ellipsoids for non-H atoms. The intramolecular hydrogen bond is shown as a dashed line.
	Fig. 2. The crystal structure of (I), viewed along the a axis, showing one-dimensional extended chains of R²₂(16) ring motif along the c axis. Intermolecular hydrogen bonds are shown as dashed lines.

(E)-N'-(2-Hydroxybenzylidene)-2-(4-isobutylphenyl)propanohydrazide top

Crystal data top

C₂₀H₂₄N₂O₂	F(000) = 696
M_r = 324.41	D_x = 1.220 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7778 reflections
a = 5.5017 (2) Å	θ = 2.4–30.0°
b = 33.0204 (14) Å	µ = 0.08 mm⁻¹
c = 9.7279 (4) Å	T = 100 K
β = 91.731 (3)°	Block, colourless
V = 1766.45 (12) Å³	0.39 × 0.24 × 0.19 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	4059 independent reflections
Radiation source: fine-focus sealed tube	3190 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ϕ and ω scans	θ_max = 27.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −7→7
T_min = 0.970, T_max = 0.985	k = −38→42
18817 measured reflections	l = −12→12

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)] = 0.076	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.181	H atoms treated by a mixture of independent and constrained refinement
S = 1.18	w = 1/[σ²(F_o²) + (0.0443P)² + 2.5698P] where P = (F_o² + 2F_c²)/3
4059 reflections	(Δ/σ)_max < 0.001
228 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₂₀H₂₄N₂O₂	V = 1766.45 (12) Å³
M_r = 324.41	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.5017 (2) Å	µ = 0.08 mm⁻¹
b = 33.0204 (14) Å	T = 100 K
c = 9.7279 (4) Å	0.39 × 0.24 × 0.19 mm
β = 91.731 (3)°

Data collection top

Bruker SMART APEXII CCD diffractometer	4059 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3190 reflections with I > 2σ(I)
T_min = 0.970, T_max = 0.985	R_int = 0.042
18817 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.076	0 restraints
wR(F²) = 0.181	H atoms treated by a mixture of independent and constrained refinement
S = 1.18	Δρ_max = 0.26 e Å⁻³
4059 reflections	Δρ_min = −0.28 e Å⁻³
228 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 esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	−0.2604 (4)	0.18426 (6)	0.5584 (2)	0.0358 (5)
O2	0.3223 (3)	0.25847 (5)	0.60286 (15)	0.0209 (4)
N1	0.1237 (4)	0.20555 (6)	0.4218 (2)	0.0199 (5)
N2	0.3012 (4)	0.23282 (6)	0.3875 (2)	0.0210 (5)
C1	−0.1353 (6)	0.11240 (9)	0.2812 (3)	0.0364 (7)
H1A	−0.0286	0.1087	0.2099	0.044*
C2	−0.3138 (6)	0.08401 (9)	0.3013 (3)	0.0367 (8)
H2A	−0.3268	0.0614	0.2448	0.044*
C3	−0.4735 (6)	0.08962 (9)	0.4065 (4)	0.0385 (8)
H3A	−0.5952	0.0706	0.4205	0.046*
C4	−0.4540 (5)	0.12339 (9)	0.4918 (4)	0.0382 (7)
H4A	−0.5625	0.1268	0.5624	0.046*
C5	−0.2736 (5)	0.15194 (8)	0.4721 (3)	0.0285 (6)
C6	−0.1095 (5)	0.14680 (8)	0.3650 (3)	0.0269 (6)
C7	0.0819 (5)	0.17603 (8)	0.3390 (3)	0.0276 (6)
H7A	0.1748	0.1732	0.2613	0.033*
C8	0.3850 (4)	0.25968 (7)	0.4827 (2)	0.0156 (5)
C9	0.5550 (5)	0.29208 (8)	0.4303 (3)	0.0235 (5)
H9A	0.6170	0.2834	0.3417	0.028*
C10	0.4016 (5)	0.33029 (8)	0.4081 (3)	0.0235 (5)
C11	0.4132 (5)	0.36299 (8)	0.4983 (3)	0.0310 (6)
H11A	0.5260	0.3628	0.5715	0.037*
C12	0.2587 (5)	0.39598 (8)	0.4807 (3)	0.0277 (6)
H12A	0.2735	0.4177	0.5411	0.033*
C13	0.0842 (6)	0.39741 (8)	0.3763 (3)	0.0277 (6)
C14	0.0756 (8)	0.36506 (9)	0.2855 (3)	0.0518 (11)
H14A	−0.0389	0.3652	0.2131	0.062*
C15	0.2335 (7)	0.33241 (9)	0.2998 (3)	0.0438 (9)
H15A	0.2259	0.3116	0.2354	0.053*
C16	−0.0929 (6)	0.43214 (8)	0.3616 (3)	0.0319 (7)
H16A	−0.1484	0.4392	0.4522	0.038*
H16B	−0.2334	0.4230	0.3075	0.038*
C17	0.0063 (6)	0.47049 (8)	0.2944 (3)	0.0331 (7)
H17A	0.1393	0.4809	0.3537	0.040*
C18	−0.1918 (7)	0.50278 (9)	0.2851 (3)	0.0435 (8)
H18A	−0.1264	0.5272	0.2472	0.065*
H18B	−0.2499	0.5082	0.3754	0.065*
H18C	−0.3239	0.4933	0.2270	0.065*
C19	0.1076 (7)	0.46188 (9)	0.1530 (3)	0.0402 (8)
H19A	0.1558	0.4869	0.1114	0.060*
H19B	−0.0152	0.4491	0.0960	0.060*
H19C	0.2460	0.4443	0.1628	0.060*
C20	0.7674 (5)	0.29712 (9)	0.5318 (4)	0.0423 (8)
H20A	0.8636	0.2729	0.5335	0.063*
H20B	0.7074	0.3022	0.6218	0.063*
H20C	0.8658	0.3195	0.5043	0.063*
H1N2	0.346 (6)	0.2342 (9)	0.303 (3)	0.034 (9)*
H1O1	−0.127 (8)	0.1984 (12)	0.539 (4)	0.064 (13)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0260 (11)	0.0248 (10)	0.0569 (14)	−0.0014 (8)	0.0068 (10)	−0.0075 (9)
O2	0.0300 (10)	0.0253 (9)	0.0074 (7)	0.0012 (7)	0.0012 (7)	−0.0001 (7)
N1	0.0248 (11)	0.0194 (10)	0.0150 (9)	−0.0027 (8)	−0.0055 (8)	0.0027 (8)
N2	0.0329 (12)	0.0221 (11)	0.0083 (9)	−0.0060 (9)	0.0021 (8)	0.0006 (8)
C1	0.060 (2)	0.0304 (15)	0.0184 (13)	−0.0137 (14)	−0.0084 (13)	0.0022 (11)
C2	0.057 (2)	0.0258 (15)	0.0268 (14)	−0.0115 (13)	−0.0136 (14)	0.0030 (12)
C3	0.0319 (16)	0.0256 (15)	0.057 (2)	−0.0059 (12)	−0.0153 (15)	0.0061 (14)
C4	0.0206 (14)	0.0292 (15)	0.065 (2)	0.0004 (11)	−0.0005 (14)	−0.0014 (14)
C5	0.0243 (13)	0.0198 (13)	0.0409 (16)	0.0032 (10)	−0.0087 (12)	0.0015 (11)
C6	0.0379 (15)	0.0226 (13)	0.0192 (12)	−0.0055 (11)	−0.0128 (11)	0.0059 (10)
C7	0.0434 (16)	0.0256 (14)	0.0134 (11)	−0.0049 (12)	−0.0048 (11)	0.0025 (10)
C8	0.0146 (11)	0.0190 (11)	0.0132 (10)	0.0031 (9)	−0.0001 (8)	0.0004 (9)
C9	0.0239 (13)	0.0202 (12)	0.0272 (13)	−0.0009 (10)	0.0118 (10)	−0.0033 (10)
C10	0.0311 (14)	0.0191 (12)	0.0212 (12)	−0.0024 (10)	0.0130 (10)	0.0016 (10)
C11	0.0232 (14)	0.0261 (14)	0.0435 (16)	−0.0025 (11)	−0.0013 (12)	−0.0117 (12)
C12	0.0255 (14)	0.0239 (13)	0.0339 (15)	−0.0010 (11)	0.0057 (11)	−0.0101 (11)
C13	0.0454 (17)	0.0201 (13)	0.0181 (12)	0.0021 (11)	0.0076 (11)	0.0042 (10)
C14	0.105 (3)	0.0295 (16)	0.0196 (14)	0.0204 (18)	−0.0219 (17)	−0.0017 (12)
C15	0.095 (3)	0.0228 (14)	0.0131 (12)	0.0159 (16)	−0.0038 (15)	−0.0027 (11)
C16	0.0447 (18)	0.0244 (14)	0.0265 (14)	0.0061 (12)	0.0002 (12)	0.0016 (11)
C17	0.0498 (19)	0.0229 (14)	0.0262 (14)	0.0030 (12)	−0.0069 (13)	0.0019 (11)
C18	0.062 (2)	0.0271 (15)	0.0413 (18)	0.0081 (15)	−0.0068 (16)	0.0036 (13)
C19	0.057 (2)	0.0328 (16)	0.0305 (16)	0.0008 (14)	−0.0011 (14)	0.0074 (13)
C20	0.0220 (14)	0.0266 (15)	0.078 (2)	−0.0012 (11)	−0.0006 (15)	−0.0134 (15)

Geometric parameters (Å, º) top

O1—C5	1.359 (3)	C11—C12	1.389 (4)
O1—H1O1	0.89 (4)	C11—H11A	0.9300
O2—C8	1.229 (3)	C12—C13	1.377 (4)
N1—C7	1.281 (3)	C12—H12A	0.9300
N1—N2	1.377 (3)	C13—C14	1.386 (4)
N2—C8	1.354 (3)	C13—C16	1.509 (4)
N2—H1N2	0.86 (3)	C14—C15	1.389 (4)
C1—C2	1.376 (4)	C14—H14A	0.9300
C1—C6	1.403 (4)	C15—H15A	0.9300
C1—H1A	0.9300	C16—C17	1.533 (4)
C2—C3	1.382 (5)	C16—H16A	0.9700
C2—H2A	0.9300	C16—H16B	0.9700
C3—C4	1.392 (4)	C17—C18	1.526 (4)
C3—H3A	0.9300	C17—C19	1.526 (4)
C4—C5	1.387 (4)	C17—H17A	0.9800
C4—H4A	0.9300	C18—H18A	0.9600
C5—C6	1.409 (4)	C18—H18B	0.9600
C6—C7	1.456 (4)	C18—H18C	0.9600
C7—H7A	0.9300	C19—H19A	0.9600
C8—C9	1.519 (3)	C19—H19B	0.9600
C9—C20	1.516 (4)	C19—H19C	0.9600
C9—C10	1.530 (4)	C20—H20A	0.9600
C9—H9A	0.9800	C20—H20B	0.9600
C10—C15	1.382 (4)	C20—H20C	0.9600
C10—C11	1.392 (4)

C5—O1—H1O1	108 (3)	C13—C12—H12A	119.1
C7—N1—N2	117.4 (2)	C11—C12—H12A	119.1
C8—N2—N1	119.4 (2)	C12—C13—C14	117.0 (3)
C8—N2—H1N2	121 (2)	C12—C13—C16	122.0 (2)
N1—N2—H1N2	119 (2)	C14—C13—C16	121.0 (3)
C2—C1—C6	122.0 (3)	C13—C14—C15	121.6 (3)
C2—C1—H1A	119.0	C13—C14—H14A	119.2
C6—C1—H1A	119.0	C15—C14—H14A	119.2
C1—C2—C3	119.1 (3)	C10—C15—C14	121.2 (3)
C1—C2—H2A	120.4	C10—C15—H15A	119.4
C3—C2—H2A	120.4	C14—C15—H15A	119.4
C2—C3—C4	120.6 (3)	C13—C16—C17	115.5 (3)
C2—C3—H3A	119.7	C13—C16—H16A	108.4
C4—C3—H3A	119.7	C17—C16—H16A	108.4
C5—C4—C3	120.3 (3)	C13—C16—H16B	108.4
C5—C4—H4A	119.8	C17—C16—H16B	108.4
C3—C4—H4A	119.8	H16A—C16—H16B	107.5
O1—C5—C4	118.3 (3)	C18—C17—C19	110.9 (2)
O1—C5—C6	121.9 (2)	C18—C17—C16	109.8 (3)
C4—C5—C6	119.8 (3)	C19—C17—C16	112.0 (2)
C1—C6—C5	118.1 (3)	C18—C17—H17A	108.0
C1—C6—C7	119.8 (3)	C19—C17—H17A	108.0
C5—C6—C7	122.1 (2)	C16—C17—H17A	108.0
N1—C7—C6	120.8 (3)	C17—C18—H18A	109.5
N1—C7—H7A	119.6	C17—C18—H18B	109.5
C6—C7—H7A	119.6	H18A—C18—H18B	109.5
O2—C8—N2	122.0 (2)	C17—C18—H18C	109.5
O2—C8—C9	122.4 (2)	H18A—C18—H18C	109.5
N2—C8—C9	115.6 (2)	H18B—C18—H18C	109.5
C20—C9—C8	109.2 (2)	C17—C19—H19A	109.5
C20—C9—C10	114.4 (2)	C17—C19—H19B	109.5
C8—C9—C10	106.6 (2)	H19A—C19—H19B	109.5
C20—C9—H9A	108.8	C17—C19—H19C	109.5
C8—C9—H9A	108.8	H19A—C19—H19C	109.5
C10—C9—H9A	108.8	H19B—C19—H19C	109.5
C15—C10—C11	117.3 (3)	C9—C20—H20A	109.5
C15—C10—C9	120.2 (2)	C9—C20—H20B	109.5
C11—C10—C9	122.4 (2)	H20A—C20—H20B	109.5
C12—C11—C10	120.9 (3)	C9—C20—H20C	109.5
C12—C11—H11A	119.5	H20A—C20—H20C	109.5
C10—C11—H11A	119.5	H20B—C20—H20C	109.5
C13—C12—C11	121.9 (3)

C7—N1—N2—C8	−167.2 (2)	N2—C8—C9—C10	99.7 (2)
C6—C1—C2—C3	0.4 (4)	C20—C9—C10—C15	167.3 (3)
C1—C2—C3—C4	−0.3 (4)	C8—C9—C10—C15	−71.9 (3)
C2—C3—C4—C5	0.0 (4)	C20—C9—C10—C11	−16.6 (4)
C3—C4—C5—O1	−179.5 (3)	C8—C9—C10—C11	104.2 (3)
C3—C4—C5—C6	0.1 (4)	C15—C10—C11—C12	1.0 (4)
C2—C1—C6—C5	−0.2 (4)	C9—C10—C11—C12	−175.2 (3)
C2—C1—C6—C7	−179.7 (3)	C10—C11—C12—C13	1.7 (4)
O1—C5—C6—C1	179.6 (2)	C11—C12—C13—C14	−2.5 (5)
C4—C5—C6—C1	0.0 (4)	C11—C12—C13—C16	176.6 (3)
O1—C5—C6—C7	−0.9 (4)	C12—C13—C14—C15	0.7 (5)
C4—C5—C6—C7	179.4 (3)	C16—C13—C14—C15	−178.4 (3)
N2—N1—C7—C6	−177.5 (2)	C11—C10—C15—C14	−2.8 (5)
C1—C6—C7—N1	−173.3 (2)	C9—C10—C15—C14	173.5 (3)
C5—C6—C7—N1	7.3 (4)	C13—C14—C15—C10	2.0 (6)
N1—N2—C8—O2	6.1 (3)	C12—C13—C16—C17	79.8 (3)
N1—N2—C8—C9	−172.1 (2)	C14—C13—C16—C17	−101.1 (3)
O2—C8—C9—C20	45.5 (3)	C13—C16—C17—C18	179.5 (2)
N2—C8—C9—C20	−136.3 (2)	C13—C16—C17—C19	55.8 (3)
O2—C8—C9—C10	−78.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O2ⁱ	0.87 (3)	1.96 (3)	2.790 (2)	159 (3)
O1—H1O1···N1	0.90 (4)	1.83 (4)	2.626 (3)	147 (4)
C14—H14A···O1ⁱ	0.93	2.51	3.272 (4)	139
C20—H20C···Cg1ⁱⁱ	0.96	2.80	3.722 (3)	161

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

Experimental details

Crystal data
Chemical formula	C₂₀H₂₄N₂O₂
M_r	324.41
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	5.5017 (2), 33.0204 (14), 9.7279 (4)
β (°)	91.731 (3)
V (Å³)	1766.45 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.39 × 0.24 × 0.19

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.970, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	18817, 4059, 3190
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.076, 0.181, 1.18
No. of reflections	4059
No. of parameters	228
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.28

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
N2—H1N2···O2ⁱ	0.87 (3)	1.96 (3)	2.790 (2)	159 (3)
O1—H1O1···N1	0.90 (4)	1.83 (4)	2.626 (3)	147 (4)
C14—H14A···O1ⁱ	0.93	2.51	3.272 (4)	139
C20—H20C···Cg1ⁱⁱ	0.96	2.80	3.722 (3)	161

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

Footnotes

‡Thomson Reuters ResearcherID: C-7576-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and JHG thank Universiti Sains Malaysia (USM) for the Research University Golden Goose grant (No. 1001/PFIZIK/811012). JHG also thanks USM for the award of a USM fellowship.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bedia, K.-K., Elçin, O., Seda, U., Fatma, K., Nathaly, S., Sevim, R. & Dimoglo, A. (2006). Eur. J. Med. Chem. 41, 1253–1261. Web of Science CrossRef PubMed CAS Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Fun, H.-K., Goh, J. H., Padaki, M., Malladi, S. & Isloor, A. M. (2009a). Acta Cryst. E65, o1591–o1592. Web of Science CSD CrossRef IUCr Journals Google Scholar
Fun, H.-K., Goh, J. H., Vinayaka, A. C. & Kalluraya, B. (2009b). Acta Cryst. E65, o2094. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rodrìguez-Argüelles, M. C., Ferrari, M. B., Bisceglie, F., Pelizzi, C., Pelosi, G., Pinelli, S. & Sassi, M. (2004). J. Inorg. Biochem. 98, 313–321. Web of Science PubMed Google Scholar
Rollas, S., Gulerman, N. & Erdeniz, H. (2002). Il Farmaco, 57, 171–174. 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. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Terzioglu, N. & Gürsoy, A. (2003). Eur. J. Med. Chem. 38, 781–786. Web of Science CrossRef PubMed CAS Google Scholar