Ethyl 1-sec-butyl-2-p-tolyl-1H-benzimidazole-5-carboxyl­ate

Arumugam, N.; Abdul Rahim, A.S.; Osman, H.; Yeap, C.S.; Fun, H.-K.

doi:10.1107/S1600536810015242

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 5| May 2010| Pages o1214-o1215

https://doi.org/10.1107/S1600536810015242

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Ethyl 1-sec-butyl-2-p-tolyl-1H-benzimidazole-5-carboxylate

Natarajan Arumugam,^a Aisyah Saad Abdul Rahim,^a ‡ Hasnah Osman,^b Chin Sing Yeap ^c § and Hoong-Kun Fun ^c ^*¶

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

(Received 6 April 2010; accepted 26 April 2010; online 30 April 2010)

In the title compound, C₂₁H₂₄N₂O₂, the butyl group is disordered over two orientations with refined site occupancies of 0.883 (3) and 0.117 (3). The dihedral angle between the mean plane of benzimidazole ring system and the benzene ring is 39.32 (4)° and the dihedral angle between the mean plane of carboxylate group and the benzimidazole ring system is 6.87 (5)°. A weak intramolecular C—H⋯π interaction may have some influence on the conformation of the molecule. In the crystal structure, molecules are linked into infinite chains along the b axis by weak intermolecular C—H⋯O hydrogen bonds.

Related literature

For background information on benzimidazole derivatives, their biological activity and medical applications, see: Richter (1997 ); Can-Eke et al. (1998 ); Evans et al. (1997 ); Garuti et al. (2000 ); Sondhi et al. (2005 ). For the synthesis of the title compound and related structures, see: Arumugam et al. (2010a ,b ,c ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₁H₂₄N₂O₂
M_r = 336.42
Monoclinic, P 2₁ /c
a = 10.6093 (7) Å
b = 12.5617 (9) Å
c = 13.6025 (10) Å
β = 96.412 (2)°
V = 1801.5 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.46 × 0.29 × 0.24 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.964, T_max = 0.981
31247 measured reflections
8425 independent reflections
6598 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.177
S = 1.08
8425 reflections
249 parameters
H-atom parameters constrained
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is centroid of the N1/C7/N2/C13/C8 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12A⋯O1ⁱ	0.93	2.58	3.5007 (13)	173
C20—H20C⋯Cg1	0.96	2.72	3.3432 (13)	123
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); 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: https://doi.org/10.1107/S1600536810015242/lh5024sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810015242/lh5024Isup2.hkl

checkCIF report

Comment top

Benzimidazoles are important heterocyclic compounds from the view point of their biological activities. Substituted benzimidazole derivatives have diverse therapeutic applications as they exhibit antiulcerative (Richter, 1997), antioxidant (Can-Eke et al., 1998), anti-HIV-1 (Evans et al., 1997), antiproliferative (Garuti et al., 2000) and antikinase (Sondhi et al., 2005) activities. In view of their importance, the crystal structure determination of the title compound was carried out and the results are presented herein.

The geometric parameters of the title compound (Fig. 1) are comparable to those closely related structures (Arumugam et al., 2010a,b,c). The butyl group is disordered over two positions with refined site-occupancies of 0.883 (3) and 0.117 (3). The dihedral angle between the mean plane of benzimidazole ring system (C7/N1/C8–C13/N2) and the benzene ring (C1–C6) is 39.32 (4)°. The mean plane of carboxylate group (O1/O2/C14–C16) is slightly twisted from the mean plane of benzimidazole ring system with a dihedral angle of 6.87 (5)°. In the crystal structure, the molecules are linked into infinite one-dimensional chains along b axis by intermolecular C12—H12A···O1ⁱ hydrogen bonds (Fig. 2, Table 1). A weak intramolecular C20—H20C···Cg1 interaction may have some influence on the conformation of the molecule (Table 1).

Related literature top

For background information on benzimidazole derivatives, their biological activity and medical applications, see: Richter (1997); Can-Eke et al. (1998); Evans et al. (1997); Garuti et al. (2000); Sondhi et al. (2005). For the synthesis of the title compound and related structures, see: Arumugam et al. (2010a,b,c). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

The title compound was synthesised using the previous procedures (Arumugam et al., 2010a,b,c) and recrystallized from EtOAc by slow evaporation technique.

Structure description top

For background information on benzimidazole derivatives, their biological activity and medical applications, see: Richter (1997); Can-Eke et al. (1998); Evans et al. (1997); Garuti et al. (2000); Sondhi et al. (2005). For the synthesis of the title compound and related structures, see: Arumugam et al. (2010a,b,c). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 atom labels and 50% probability displacement ellipsoids for non-H atoms. All disorder components are shown.
	Fig. 2. The crystal packing of the title compound, viewed along the a axis, showing one-dimensional chains along the b axis. Intermolecular hydrogen bonds are shown as dashed lines. Only the major disorder component is shown.

Ethyl 1-sec-butyl-2-p-tolyl-1H-benzimidazole-5-carboxylate top

Crystal data top

C₂₁H₂₄N₂O₂	F(000) = 720
M_r = 336.42	D_x = 1.240 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9348 reflections
a = 10.6093 (7) Å	θ = 2.5–35.7°
b = 12.5617 (9) Å	µ = 0.08 mm⁻¹
c = 13.6025 (10) Å	T = 100 K
β = 96.412 (2)°	Block, colourless
V = 1801.5 (2) Å³	0.46 × 0.29 × 0.24 mm
Z = 4

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	8425 independent reflections
Radiation source: fine-focus sealed tube	6598 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
φ and ω scans	θ_max = 35.9°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −17→17
T_min = 0.964, T_max = 0.981	k = −20→18
31247 measured reflections	l = −22→22

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.177	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0965P)² + 0.2974P] where P = (F_o² + 2F_c²)/3
8425 reflections	(Δ/σ)_max = 0.001
249 parameters	Δρ_max = 0.58 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₂₁H₂₄N₂O₂	V = 1801.5 (2) Å³
M_r = 336.42	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.6093 (7) Å	µ = 0.08 mm⁻¹
b = 12.5617 (9) Å	T = 100 K
c = 13.6025 (10) Å	0.46 × 0.29 × 0.24 mm
β = 96.412 (2)°

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	8425 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	6598 reflections with I > 2σ(I)
T_min = 0.964, T_max = 0.981	R_int = 0.050
31247 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.177	H-atom parameters constrained
S = 1.08	Δρ_max = 0.58 e Å⁻³
8425 reflections	Δρ_min = −0.35 e Å⁻³
249 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems 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	Occ. (<1)
O1	0.49342 (7)	0.02746 (7)	0.17217 (6)	0.02380 (16)
O2	0.65726 (7)	−0.02944 (6)	0.09409 (6)	0.02268 (16)
N1	0.97240 (7)	0.27803 (6)	0.12066 (6)	0.01543 (14)
N2	0.88175 (7)	0.41780 (6)	0.19145 (6)	0.01655 (14)
C1	1.08554 (9)	0.54848 (8)	0.10257 (7)	0.01777 (16)
H1A	1.0063	0.5810	0.0955	0.021*
C2	1.19164 (9)	0.60526 (8)	0.08166 (7)	0.01913 (17)
H2A	1.1826	0.6757	0.0611	0.023*
C3	1.31155 (9)	0.55829 (8)	0.09096 (7)	0.01821 (16)
C4	1.32288 (9)	0.45317 (8)	0.12279 (8)	0.02007 (17)
H4A	1.4023	0.4209	0.1299	0.024*
C5	1.21734 (8)	0.39545 (8)	0.14411 (7)	0.01823 (16)
H5A	1.2267	0.3251	0.1651	0.022*
C6	1.09738 (8)	0.44266 (7)	0.13421 (7)	0.01533 (15)
C7	0.98590 (8)	0.37775 (7)	0.15004 (7)	0.01501 (15)
C8	0.85266 (8)	0.24973 (7)	0.14314 (6)	0.01444 (14)
C9	0.78890 (8)	0.15330 (7)	0.12648 (7)	0.01558 (15)
H9A	0.8262	0.0964	0.0969	0.019*
C10	0.66749 (8)	0.14490 (7)	0.15547 (7)	0.01544 (15)
C11	0.61067 (8)	0.23144 (8)	0.19943 (7)	0.01795 (16)
H11A	0.5293	0.2235	0.2176	0.022*
C12	0.67222 (9)	0.32803 (8)	0.21644 (7)	0.01830 (16)
H12A	0.6344	0.3848	0.2457	0.022*
C13	0.79460 (8)	0.33574 (7)	0.18720 (7)	0.01546 (15)
C14	0.59579 (9)	0.04345 (8)	0.14279 (7)	0.01746 (16)
C15	0.59689 (11)	−0.13214 (8)	0.07980 (9)	0.0248 (2)
H15A	0.5092	−0.1239	0.0519	0.030*
H15B	0.5987	−0.1694	0.1424	0.030*
C16	0.67033 (12)	−0.19304 (10)	0.00983 (10)	0.0309 (2)
H16A	0.6344	−0.2628	−0.0007	0.046*
H16B	0.7572	−0.1992	0.0377	0.046*
H16C	0.6662	−0.1560	−0.0522	0.046*
C17	0.88130 (11)	0.51250 (9)	0.25531 (10)	0.0177 (2)	0.883 (3)
H17A	0.9632	0.5481	0.2535	0.021*	0.883 (3)
C18	0.77857 (12)	0.59232 (10)	0.21723 (12)	0.0295 (3)	0.883 (3)
H18A	0.7830	0.6054	0.1482	0.044*	0.883 (3)
H18B	0.7915	0.6578	0.2533	0.044*	0.883 (3)
H18C	0.6967	0.5639	0.2263	0.044*	0.883 (3)
C19	0.87392 (12)	0.47809 (11)	0.36205 (9)	0.0252 (3)	0.883 (3)
H19A	0.8852	0.5399	0.4048	0.030*	0.883 (3)
H19B	0.7904	0.4489	0.3678	0.030*	0.883 (3)
C20	0.97390 (13)	0.39537 (13)	0.39635 (9)	0.0283 (3)	0.883 (3)
H20A	0.9696	0.3794	0.4649	0.042*	0.883 (3)
H20B	1.0565	0.4228	0.3880	0.042*	0.883 (3)
H20C	0.9588	0.3317	0.3578	0.042*	0.883 (3)
C17B	0.9123 (10)	0.4910 (8)	0.2883 (8)	0.0205 (17)*	0.117 (3)
H17B	0.9914	0.5291	0.2810	0.025*	0.117 (3)
C18B	0.9279 (12)	0.4407 (10)	0.3838 (8)	0.028 (2)*	0.117 (3)
H18D	0.9359	0.4942	0.4345	0.042*	0.117 (3)
H18E	1.0028	0.3973	0.3895	0.042*	0.117 (3)
H18F	0.8553	0.3970	0.3912	0.042*	0.117 (3)
C19B	0.8068 (10)	0.5725 (9)	0.2776 (8)	0.028 (2)*	0.117 (3)
H19C	0.8237	0.6249	0.3298	0.034*	0.117 (3)
H19D	0.7281	0.5370	0.2878	0.034*	0.117 (3)
C20B	0.7858 (14)	0.6360 (12)	0.1703 (11)	0.041 (3)*	0.117 (3)
H20D	0.7288	0.6946	0.1751	0.061*	0.117 (3)
H20E	0.7507	0.5879	0.1196	0.061*	0.117 (3)
H20F	0.8659	0.6623	0.1541	0.061*	0.117 (3)
C21	1.42509 (11)	0.62003 (10)	0.06554 (8)	0.0258 (2)
H21A	1.5001	0.5936	0.1038	0.039*
H21B	1.4142	0.6940	0.0802	0.039*
H21C	1.4334	0.6119	−0.0036	0.039*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0180 (3)	0.0222 (4)	0.0325 (4)	−0.0070 (2)	0.0084 (3)	−0.0006 (3)
O2	0.0226 (3)	0.0155 (3)	0.0316 (4)	−0.0089 (2)	0.0100 (3)	−0.0062 (3)
N1	0.0142 (3)	0.0130 (3)	0.0200 (3)	−0.0026 (2)	0.0059 (2)	−0.0017 (2)
N2	0.0157 (3)	0.0132 (3)	0.0217 (3)	−0.0031 (2)	0.0066 (3)	−0.0045 (2)
C1	0.0181 (4)	0.0147 (4)	0.0207 (4)	−0.0026 (3)	0.0031 (3)	0.0002 (3)
C2	0.0231 (4)	0.0151 (4)	0.0195 (4)	−0.0057 (3)	0.0035 (3)	0.0004 (3)
C3	0.0187 (4)	0.0190 (4)	0.0175 (4)	−0.0073 (3)	0.0046 (3)	−0.0017 (3)
C4	0.0163 (4)	0.0195 (4)	0.0252 (4)	−0.0035 (3)	0.0057 (3)	0.0000 (3)
C5	0.0160 (3)	0.0152 (4)	0.0242 (4)	−0.0019 (3)	0.0056 (3)	0.0004 (3)
C6	0.0153 (3)	0.0138 (4)	0.0174 (3)	−0.0034 (3)	0.0044 (3)	−0.0016 (3)
C7	0.0141 (3)	0.0135 (4)	0.0181 (3)	−0.0025 (2)	0.0047 (3)	−0.0014 (3)
C8	0.0139 (3)	0.0123 (3)	0.0178 (3)	−0.0025 (2)	0.0045 (3)	−0.0015 (3)
C9	0.0155 (3)	0.0127 (3)	0.0192 (4)	−0.0028 (3)	0.0048 (3)	−0.0018 (3)
C10	0.0153 (3)	0.0139 (4)	0.0175 (3)	−0.0037 (3)	0.0037 (3)	−0.0001 (3)
C11	0.0145 (3)	0.0184 (4)	0.0217 (4)	−0.0024 (3)	0.0056 (3)	−0.0012 (3)
C12	0.0153 (3)	0.0168 (4)	0.0238 (4)	−0.0016 (3)	0.0068 (3)	−0.0038 (3)
C13	0.0142 (3)	0.0135 (4)	0.0193 (4)	−0.0026 (3)	0.0047 (3)	−0.0028 (3)
C14	0.0166 (3)	0.0162 (4)	0.0197 (4)	−0.0044 (3)	0.0027 (3)	0.0008 (3)
C15	0.0265 (5)	0.0175 (4)	0.0314 (5)	−0.0108 (3)	0.0076 (4)	−0.0043 (4)
C16	0.0303 (5)	0.0212 (5)	0.0426 (6)	−0.0081 (4)	0.0110 (5)	−0.0081 (4)
C17	0.0177 (4)	0.0137 (4)	0.0224 (5)	−0.0019 (3)	0.0046 (4)	−0.0060 (4)
C18	0.0230 (5)	0.0171 (5)	0.0492 (9)	0.0041 (4)	0.0076 (5)	−0.0052 (5)
C19	0.0232 (5)	0.0321 (7)	0.0213 (5)	−0.0070 (5)	0.0070 (4)	−0.0101 (4)
C20	0.0289 (6)	0.0361 (7)	0.0195 (5)	−0.0105 (5)	0.0007 (4)	0.0019 (4)
C21	0.0246 (4)	0.0261 (5)	0.0280 (5)	−0.0124 (4)	0.0090 (4)	−0.0016 (4)

Geometric parameters (Å, º) top

O1—C14	1.2151 (11)	C15—H15A	0.9700
O2—C14	1.3412 (12)	C15—H15B	0.9700
O2—C15	1.4438 (12)	C16—H16A	0.9600
N1—C7	1.3178 (12)	C16—H16B	0.9600
N1—C8	1.3858 (11)	C16—H16C	0.9600
N2—C13	1.3817 (11)	C17—C19	1.5253 (18)
N2—C7	1.3895 (11)	C17—C18	1.5281 (19)
N2—C17	1.4733 (13)	C17—H17A	0.9800
N2—C17B	1.609 (10)	C18—H18A	0.9600
C1—C2	1.3886 (13)	C18—H18B	0.9600
C1—C6	1.3985 (13)	C18—H18C	0.9600
C1—H1A	0.9300	C19—C20	1.521 (2)
C2—C3	1.3952 (14)	C19—H19A	0.9700
C2—H2A	0.9300	C19—H19B	0.9700
C3—C4	1.3907 (14)	C20—H20A	0.9600
C3—C21	1.5051 (13)	C20—H20B	0.9600
C4—C5	1.3914 (13)	C20—H20C	0.9600
C4—H4A	0.9300	C17B—C18B	1.438 (16)
C5—C6	1.3969 (13)	C17B—C19B	1.512 (15)
C5—H5A	0.9300	C17B—H17B	0.9800
C6—C7	1.4720 (12)	C18B—H18D	0.9600
C8—C9	1.3935 (12)	C18B—H18E	0.9600
C8—C13	1.4101 (12)	C18B—H18F	0.9600
C9—C10	1.3926 (12)	C19B—C20B	1.656 (19)
C9—H9A	0.9300	C19B—H19C	0.9700
C10—C11	1.4083 (13)	C19B—H19D	0.9700
C10—C14	1.4842 (13)	C20B—H20D	0.9600
C11—C12	1.3851 (13)	C20B—H20E	0.9600
C11—H11A	0.9300	C20B—H20F	0.9600
C12—C13	1.4031 (12)	C21—H21A	0.9600
C12—H12A	0.9300	C21—H21B	0.9600
C15—C16	1.5047 (17)	C21—H21C	0.9600

C14—O2—C15	116.33 (8)	O2—C15—H15B	110.4
C7—N1—C8	104.38 (7)	C16—C15—H15B	110.4
C13—N2—C7	105.76 (7)	H15A—C15—H15B	108.6
C13—N2—C17	125.52 (8)	C15—C16—H16A	109.5
C7—N2—C17	125.91 (8)	C15—C16—H16B	109.5
C13—N2—C17B	122.2 (4)	H16A—C16—H16B	109.5
C7—N2—C17B	116.2 (4)	C15—C16—H16C	109.5
C2—C1—C6	120.28 (9)	H16A—C16—H16C	109.5
C2—C1—H1A	119.9	H16B—C16—H16C	109.5
C6—C1—H1A	119.9	N2—C17—C19	109.65 (10)
C1—C2—C3	121.07 (9)	N2—C17—C18	112.27 (11)
C1—C2—H2A	119.5	C19—C17—C18	113.46 (10)
C3—C2—H2A	119.5	N2—C17—H17A	107.0
C4—C3—C2	118.42 (8)	C19—C17—H17A	107.0
C4—C3—C21	121.15 (9)	C18—C17—H17A	107.0
C2—C3—C21	120.42 (10)	C20—C19—C17	112.18 (10)
C3—C4—C5	121.07 (9)	C20—C19—H19A	109.2
C3—C4—H4A	119.5	C17—C19—H19A	109.2
C5—C4—H4A	119.5	C20—C19—H19B	109.2
C4—C5—C6	120.29 (9)	C17—C19—H19B	109.2
C4—C5—H5A	119.9	H19A—C19—H19B	107.9
C6—C5—H5A	119.9	C18B—C17B—C19B	113.2 (9)
C5—C6—C1	118.86 (8)	C18B—C17B—N2	118.7 (8)
C5—C6—C7	119.27 (8)	C19B—C17B—N2	103.2 (8)
C1—C6—C7	121.71 (8)	C18B—C17B—H17B	107.0
N1—C7—N2	113.75 (7)	C19B—C17B—H17B	107.0
N1—C7—C6	122.96 (8)	N2—C17B—H17B	107.0
N2—C7—C6	123.17 (8)	C17B—C18B—H18D	109.5
N1—C8—C9	128.86 (8)	C17B—C18B—H18E	109.5
N1—C8—C13	110.60 (7)	H18D—C18B—H18E	109.5
C9—C8—C13	120.53 (8)	C17B—C18B—H18F	109.5
C10—C9—C8	117.86 (8)	H18D—C18B—H18F	109.5
C10—C9—H9A	121.1	H18E—C18B—H18F	109.5
C8—C9—H9A	121.1	C17B—C19B—C20B	115.8 (9)
C9—C10—C11	121.00 (8)	C17B—C19B—H19C	108.3
C9—C10—C14	120.69 (8)	C20B—C19B—H19C	108.3
C11—C10—C14	118.29 (8)	C17B—C19B—H19D	108.3
C12—C11—C10	122.07 (8)	C20B—C19B—H19D	108.3
C12—C11—H11A	119.0	H19C—C19B—H19D	107.4
C10—C11—H11A	119.0	C19B—C20B—H20D	109.5
C11—C12—C13	116.55 (8)	C19B—C20B—H20E	109.5
C11—C12—H12A	121.7	H20D—C20B—H20E	109.5
C13—C12—H12A	121.7	C19B—C20B—H20F	109.5
N2—C13—C12	132.51 (8)	H20D—C20B—H20F	109.5
N2—C13—C8	105.51 (7)	H20E—C20B—H20F	109.5
C12—C13—C8	121.98 (8)	C3—C21—H21A	109.5
O1—C14—O2	123.46 (9)	C3—C21—H21B	109.5
O1—C14—C10	124.68 (9)	H21A—C21—H21B	109.5
O2—C14—C10	111.86 (8)	C3—C21—H21C	109.5
O2—C15—C16	106.63 (8)	H21A—C21—H21C	109.5
O2—C15—H15A	110.4	H21B—C21—H21C	109.5
C16—C15—H15A	110.4

C6—C1—C2—C3	0.45 (15)	C17B—N2—C13—C12	44.5 (5)
C1—C2—C3—C4	−0.67 (14)	C7—N2—C13—C8	0.23 (10)
C1—C2—C3—C21	178.44 (9)	C17—N2—C13—C8	−161.60 (10)
C2—C3—C4—C5	0.58 (15)	C17B—N2—C13—C8	−135.9 (5)
C21—C3—C4—C5	−178.53 (9)	C11—C12—C13—N2	179.26 (10)
C3—C4—C5—C6	−0.26 (15)	C11—C12—C13—C8	−0.27 (14)
C4—C5—C6—C1	0.02 (14)	N1—C8—C13—N2	−0.09 (10)
C4—C5—C6—C7	175.50 (9)	C9—C8—C13—N2	−179.20 (8)
C2—C1—C6—C5	−0.12 (14)	N1—C8—C13—C12	179.55 (9)
C2—C1—C6—C7	−175.48 (9)	C9—C8—C13—C12	0.43 (14)
C8—N1—C7—N2	0.25 (10)	C15—O2—C14—O1	−1.73 (15)
C8—N1—C7—C6	−175.82 (8)	C15—O2—C14—C10	178.60 (8)
C13—N2—C7—N1	−0.31 (11)	C9—C10—C14—O1	174.76 (10)
C17—N2—C7—N1	161.42 (10)	C11—C10—C14—O1	−3.91 (15)
C17B—N2—C7—N1	138.9 (4)	C9—C10—C14—O2	−5.57 (13)
C13—N2—C7—C6	175.74 (9)	C11—C10—C14—O2	175.76 (8)
C17—N2—C7—C6	−22.52 (15)	C14—O2—C15—C16	170.62 (10)
C17B—N2—C7—C6	−45.1 (5)	C13—N2—C17—C19	51.97 (14)
C5—C6—C7—N1	−38.44 (13)	C7—N2—C17—C19	−106.28 (11)
C1—C6—C7—N1	136.90 (10)	C17B—N2—C17—C19	−36.7 (9)
C5—C6—C7—N2	145.86 (9)	C13—N2—C17—C18	−75.12 (14)
C1—C6—C7—N2	−38.79 (13)	C7—N2—C17—C18	126.63 (11)
C7—N1—C8—C9	178.93 (9)	C17B—N2—C17—C18	−163.7 (10)
C7—N1—C8—C13	−0.10 (10)	N2—C17—C19—C20	51.24 (13)
N1—C8—C9—C10	−179.49 (9)	C18—C17—C19—C20	177.66 (10)
C13—C8—C9—C10	−0.55 (13)	C13—N2—C17B—C18B	43.5 (10)
C8—C9—C10—C11	0.54 (14)	C7—N2—C17B—C18B	−88.4 (9)
C8—C9—C10—C14	−178.09 (8)	C17—N2—C17B—C18B	149.4 (15)
C9—C10—C11—C12	−0.41 (15)	C13—N2—C17B—C19B	−82.6 (7)
C14—C10—C11—C12	178.26 (9)	C7—N2—C17B—C19B	145.4 (5)
C10—C11—C12—C13	0.26 (14)	C17—N2—C17B—C19B	23.2 (7)
C7—N2—C13—C12	−179.36 (10)	C18B—C17B—C19B—C20B	178.5 (9)
C17—N2—C13—C12	18.81 (17)	N2—C17B—C19B—C20B	−51.9 (10)

Hydrogen-bond geometry (Å, º) top

Cg1 is centroid of the N1/C7/N2/C13/C8 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O1ⁱ	0.93	2.58	3.5007 (13)	173
C20—H20C···Cg1	0.96	2.72	3.3432 (13)	123

Symmetry code: (i) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₄N₂O₂
M_r	336.42
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	10.6093 (7), 12.5617 (9), 13.6025 (10)
β (°)	96.412 (2)
V (Å³)	1801.5 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.46 × 0.29 × 0.24

Data collection
Diffractometer	Bruker APEXII DUO CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.964, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	31247, 8425, 6598
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.825

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.177, 1.08
No. of reflections	8425
No. of parameters	249
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.35

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

Hydrogen-bond geometry (Å, º) top

Cg1 is centroid of the N1/C7/N2/C13/C8 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O1ⁱ	0.93	2.58	3.5007 (13)	173
C20—H20C···Cg1	0.96	2.72	3.3432 (13)	123

Symmetry code: (i) −x+1, y+1/2, −z+1/2.

Footnotes

‡Additional correspondence author, e-mail: aisyah@usm.my.

§Thomson Reuters ResearcherID: A-5523-2009.

¶Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

NA, ASAR and HO are grateful to Universiti Sains Malaysia (USM) for funding the synthetic chemistry work under the USM Research University Grant (1001/PFARMASI/815026). NA thanks USM for the award of a postdoctoral fellowship. HKF and CSY thank USM for the Research University Golden Goose Grant (1001/PFIZIK/811012). CSY also thanks USM for the award of a USM fellowship.

References

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